data_01 # 1. SUBMISSION DETAILS _publ_contact_author ; Itzia I. Padilla-Mart/'inez Departamento de Qu/'imica UPIBI-IPN Av. Acueducto s/n, Col. Barrio la Laguna Ticoman C.P 07340 M/'exico, D. F. ; _publ_contact_author_phone '525 729 6000 EXT 56324' _publ_contact_author_fax '525 729 6000 EXT 56325' _publ_contact_author_email ipadilla@acei.upibi.ipn.mx _publ_requested_journal 'Crystal Growth and Design' _publ_requested_category 'LC' # 3. TITLE AND AUTHOR LIST _publ_section_title ; Ethyl coumarin-3-carboxilate ; _publ_section_abstract ; The crystallographic study of 3-carboxycoumarins 1-4 and 3-amidocoumarin 5-6 is reported in the context of crystal engineering. The formers can be depicted as two fused rings with opposed polarity which appeared associated through paralled displaced pi-stacking interactions. The benzenoid ring B and the lactone ring L of one molecule interact with the ing L' and benzenoid ring B' of thepartner molecule with mean interplanar and mean intercentroid distances ranging between 3.385(6)-3.67(2)A and 3.679(1)-4.081(3)A, respectively. Among the six possible arrangements formed by pairwise overlapping the anti tail-to-tail orientation was the most frequently observed. Pairing through pi-stacking interactions is less favoured when changing the 3-carboxy for a 3-amido group or even annulled increasing the H-bonding capability of the 3-amido group as in 3-oxalamate 6. These fused polar rings can also associate through pi-stacking interactions in the presence of weak interactions such C--H..X(X=O or aromatic ring), as long as these associations do not slip so far the molecular planes to avoid subsequent pi-stacking interactions ; _publ_section_comment ; The supramolecular structure observed in 3-carboxy and 3-amidocoumarins 1-6 is directed by a balance between parallel displaced pi-stacking, weak aryl C-X..pi and strong N-H..O hydrogen bonding interactions. ; loop_ _publ_author_name _publ_author_address ; 'Efr/'en V. Garc/'ia-B/'aez' Departamento de Qu/'imica UPIBI-IPN Av. Acueducto s/n Col. Barrio la Laguna Ticoman C.P. 07340. M/'exico, D. F. ; 'Francisco J. Mart/'inez-Mart/'inez' Departamento de Qu/'imica UPIBI-IPN Av. Acueducto s/n, Col. Barrio la Laguna Ticoman C.P. 07340. M/'exico D. F. ; 'Herbert Hopfl' Centro de Investigaciones Qu/'imicas Universidad Autonoma del Estado de Morelos Cuernavaca Morelos ; _audit_creation_method SHELXL-97 _chemical_name_systematic ; Ethyl coumarin-3-carboxilate ; _chemical_name_common ? _chemical_formula_moiety ? _chemical_formula_structural ? _chemical_formula_analytical 'C12 H10 O4' _chemical_formula_sum 'C12 H10 O4' _chemical_formula_weight 218.20 _chemical_melting_point ? _chemical_compound_source ? loop_ _symmetry_cell_setting Monoclinic _symmetry_space_group_name_H-M P2(1)/c loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y-1/2, z-1/2' loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0 0 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.006 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _cell_length_a 7.9350(3) _cell_length_b 15.7742(6) _cell_length_c 8.7577(4) _cell_angle_alpha 90 _cell_angle_beta 108.2180 _cell_angle_gamma 90 _cell_volume 1041.24(7) _cell_formula_units_Z 4 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used 200 _cell_measurement_theta_min 20 _exptl_crystal_description rectangular _exptl_crystal_colour colorless _exptl_crystal_size_max 0.4 _exptl_crystal_size_mid 0.3 _exptl_crystal_size_min 0.2 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.392 _exptl_crystal_density_method ? _exptl_crystal_F_000 456 _exptl_absorpt_coefficient_mu 0.105 _exptl_absorpt_correction_type none _exptl_absorpt_correction_T_min ? _exptl_absorpt_correction_T_max ? _exptl_special_details ; Diffractometer operator H. Hopfl scanspeed_seconds/frame 10 1200 frames measured in phi (0-360) with chi=0 and om=2th=25 65 frames measured in om (15-35) with chi=280, 2th=29 and phi=0 Crystal mounted in glass fibber ; _diffrn_ambient_temperature 293(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device 'Bruker SMART Area-detector' _diffrn_measurement_method 'phi and omega scans' _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% 0 _diffrn_reflns_number 6798 _diffrn_reflns_av_R_equivalents 0.0253 _diffrn_reflns_av_sigmaI/netI 0.0199 _diffrn_reflns_limit_h_min -9 _diffrn_reflns_limit_h_max 9 _diffrn_reflns_limit_k_min -19 _diffrn_reflns_limit_k_max 19 _diffrn_reflns_limit_l_min -8 _diffrn_reflns_limit_l_max 10 _diffrn_reflns_theta_min 2.58 _diffrn_reflns_theta_max 26.00 _diffrn_reflns_theta_full 26 _diffrn_measured_fraction_theta_full 1 _diffrn_measured_fraction_theta_max 1 _reflns_number_total 2046 _reflns_number_observed 1604 _reflns_observed_criterion >2sigma(I) _computing_data_collection 'SMART (V4.C50)' _computing_cell_refinement 'SMART (V4.C50)' _computing_data_reduction 'SAINT (V4.D50)' _computing_structure_solution 'SHELXS-86 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-93 (Sheldrick, 1993)' _computing_molecular_graphics 'Cameron-WinGx (Farrugia 1997)' _computing_publication_material 'SHELXL (Sheldrick 1997)' _refine_special_details ; Refinement on F^2^ for ALL reflections except for 0 with very negative F^2^ or flagged by the user for potential systematic errors. Weighted R-factors wR and all goodnesses of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The observed criterion of F^2^ > 2sigma(F^2^) is used only for calculating _R_factor_obs etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0911P)^2^+0.0268P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary 'direct methods' _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geometrically _refine_ls_hydrogen_treatment mixed _refine_ls_extinction_method SHELXL _refine_ls_extinction_coef 0.2885(188) _refine_ls_extinction_expression 'Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^' _refine_ls_number_reflns 2046 _refine_ls_number_parameters 186 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0577 _refine_ls_R_factor_obs 0.0474 _refine_ls_wR_factor_all 0.1318 _refine_ls_wR_factor_obs 0.1227 _refine_ls_goodness_of_fit_all 1.045 _refine_ls_goodness_of_fit_obs 1.111 _refine_ls_restrained_S_all 1.045 _refine_ls_restrained_S_obs 1.111 _refine_ls_shift/esd_max 0.000 _refine_ls_shift/esd_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_thermal_displace_type _atom_site_occupancy _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_group O1 O 0.10816(14) 0.01844(6) 0.22116(12) 0.0559(3) Uani 1 d . . O2 O 0.2844(2) 0.12679(8) 0.23190(14) 0.0803(4) Uani 1 d . . O11 O 0.4528(2) 0.19220(8) 0.53707(15) 0.0766(4) Uani 1 d . . O12 O 0.50414(14) 0.09546(6) 0.73175(12) 0.0555(3) Uani 1 d . . C2 C 0.2396(2) 0.07291(9) 0.3075(2) 0.0519(4) Uani 1 d . . C3 C 0.3101(2) 0.05739(8) 0.4809(2) 0.0437(4) Uani 1 d . . C4 C 0.2651(2) -0.01368(8) 0.5440(2) 0.0445(4) Uani 1 d . . C5 C 0.0932(2) -0.14977(10) 0.5049(2) 0.0551(4) Uani 1 d . . C6 C -0.0304(2) -0.20191(10) 0.4049(2) 0.0593(4) Uani 1 d . . C7 C -0.1108(2) -0.17972(10) 0.2453(2) 0.0575(4) Uani 1 d . . C8 C -0.0662(2) -0.10555(10) 0.1849(2) 0.0552(4) Uani 1 d . . C9 C 0.0611(2) -0.05375(8) 0.2860(2) 0.0461(4) Uani 1 d . . C10 C 0.1417(2) -0.07362(8) 0.4474(2) 0.0439(4) Uani 1 d . . C11 C 0.4302(2) 0.12281(9) 0.5819(2) 0.0470(4) Uani 1 d . . C13 C 0.6070(2) 0.15754(11) 0.8465(2) 0.0612(4) Uani 1 d . . C14 C 0.6509(4) 0.1193(2) 1.0084(2) 0.0902(7) Uani 1 d . . H4A H 0.3224(19) -0.0254(9) 0.6589(19) 0.052(4) Uiso 1 d . . H13B H 0.5318(25) 0.2056(12) 0.8375(21) 0.069(5) Uiso 1 d . . H6A H -0.0603(23) -0.2548(13) 0.4480(22) 0.072(5) Uiso 1 d . . H13A H 0.7107(26) 0.1732(12) 0.8117(23) 0.078(5) Uiso 1 d . . H7A H -0.2019(23) -0.2174(11) 0.1741(22) 0.065(5) Uiso 1 d . . H14B H 0.7136(34) 0.0639(18) 1.0227(30) 0.118(9) Uiso 1 d . . H8A H -0.1169(21) -0.0883(10) 0.0776(22) 0.059(4) Uiso 1 d . . H5A H 0.1521(22) -0.1617(11) 0.6198(22) 0.064(5) Uiso 1 d . . H14A H 0.5401(38) 0.1063(16) 1.0362(30) 0.116(9) Uiso 1 d . . H14C H 0.7205(35) 0.1561(16) 1.0809(34) 0.109(8) Uiso 1 d . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 O1 0.0683(7) 0.0548(6) 0.0377(5) 0.0064(4) 0.0064(4) -0.0005(5) O2 0.1175(10) 0.0661(7) 0.0518(7) 0.0127(6) 0.0182(6) -0.0196(7) O11 0.0970(10) 0.0599(7) 0.0663(8) 0.0061(6) 0.0161(7) -0.0239(6) O12 0.0631(6) 0.0496(6) 0.0466(6) -0.0059(4) 0.0067(5) -0.0015(4) C2 0.0651(9) 0.0451(7) 0.0440(8) 0.0042(6) 0.0147(6) 0.0039(6) C3 0.0455(7) 0.0435(7) 0.0421(7) -0.0001(5) 0.0135(6) 0.0058(5) C4 0.0469(7) 0.0485(8) 0.0367(7) 0.0021(6) 0.0110(6) 0.0052(6) C5 0.0651(9) 0.0524(8) 0.0467(8) 0.0034(6) 0.0160(7) -0.0004(7) C6 0.0704(10) 0.0502(9) 0.0610(10) -0.0045(7) 0.0258(8) -0.0063(7) C7 0.0559(9) 0.0595(9) 0.0584(9) -0.0150(7) 0.0196(7) -0.0039(7) C8 0.0552(9) 0.0646(9) 0.0416(8) -0.0062(7) 0.0091(7) 0.0047(7) C9 0.0508(8) 0.0464(7) 0.0411(7) -0.0006(6) 0.0145(6) 0.0070(6) C10 0.0484(7) 0.0438(7) 0.0392(7) -0.0006(5) 0.0130(5) 0.0047(5) C11 0.0474(7) 0.0469(7) 0.0479(8) -0.0013(6) 0.0167(6) 0.0028(6) C13 0.0585(9) 0.0625(10) 0.0576(9) -0.0195(7) 0.0110(7) -0.0041(8) C14 0.108(2) 0.088(2) 0.0545(11) -0.0115(11) -0.0044(11) -0.0006(14) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag O1 C9 1.375(2) . ? O1 C2 1.380(2) . ? O2 C2 1.198(2) . ? O11 C11 1.195(2) . ? O12 C11 1.331(2) . ? O12 C13 1.457(2) . ? C2 C3 1.465(2) . ? C3 C4 1.347(2) . ? C3 C11 1.493(2) . ? C4 C10 1.432(2) . ? C4 H4A 0.98(2) . ? C5 C6 1.367(2) . ? C5 C10 1.402(2) . ? C5 H5A 0.99(2) . ? C6 C7 1.388(2) . ? C6 H6A 0.97(2) . ? C7 C8 1.375(2) . ? C7 H7A 0.99(2) . ? C8 C9 1.383(2) . ? C8 H8A 0.94(2) . ? C9 C10 1.393(2) . ? C13 C14 1.479(3) . ? C13 H13B 0.95(2) . ? C13 H13A 0.99(2) . ? C14 H14B 0.99(3) . ? C14 H14A 1.00(3) . ? C14 H14C 0.91(3) . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C9 O1 C2 123.06(11) . . ? C11 O12 C13 116.21(12) . . ? O2 C2 O1 116.29(13) . . ? O2 C2 C3 127.46(14) . . ? O1 C2 C3 116.25(12) . . ? C4 C3 C2 120.01(13) . . ? C4 C3 C11 122.28(12) . . ? C2 C3 C11 117.71(12) . . ? C3 C4 C10 121.81(12) . . ? C3 C4 H4A 118.7(9) . . ? C10 C4 H4A 119.5(9) . . ? C6 C5 C10 120.52(14) . . ? C6 C5 H5A 123.7(10) . . ? C10 C5 H5A 115.8(10) . . ? C5 C6 C7 120.35(15) . . ? C5 C6 H6A 118.7(11) . . ? C7 C6 H6A 121.0(11) . . ? C8 C7 C6 120.65(15) . . ? C8 C7 H7A 119.5(10) . . ? C6 C7 H7A 119.8(10) . . ? C7 C8 C9 118.74(14) . . ? C7 C8 H8A 123.4(10) . . ? C9 C8 H8A 117.9(10) . . ? O1 C9 C8 117.61(12) . . ? O1 C9 C10 120.48(12) . . ? C8 C9 C10 121.90(13) . . ? C9 C10 C5 117.83(13) . . ? C9 C10 C4 117.61(12) . . ? C5 C10 C4 124.54(12) . . ? O11 C11 O12 123.77(14) . . ? O11 C11 C3 124.87(14) . . ? O12 C11 C3 111.31(12) . . ? O12 C13 C14 107.5(2) . . ? O12 C13 H13B 106.0(11) . . ? C14 C13 H13B 111.0(11) . . ? O12 C13 H13A 107.1(11) . . ? C14 C13 H13A 115.3(11) . . ? H13B C13 H13A 109.5(16) . . ? C13 C14 H14B 116.0(15) . . ? C13 C14 H14A 110.8(15) . . ? H14B C14 H14A 103.4(21) . . ? C13 C14 H14C 108.5(16) . . ? H14B C14 H14C 107.6(21) . . ? H14A C14 H14C 110.4(23) . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag C9 O1 C2 O2 170.05(13) . . . . ? C9 O1 C2 C3 -9.0(2) . . . . ? O2 C2 C3 C4 -169.7(2) . . . . ? O1 C2 C3 C4 9.3(2) . . . . ? O2 C2 C3 C11 10.8(2) . . . . ? O1 C2 C3 C11 -170.21(11) . . . . ? C2 C3 C4 C10 -3.2(2) . . . . ? C11 C3 C4 C10 176.30(11) . . . . ? C10 C5 C6 C7 -0.6(2) . . . . ? C5 C6 C7 C8 0.6(2) . . . . ? C6 C7 C8 C9 0.4(2) . . . . ? C2 O1 C9 C8 -176.68(12) . . . . ? C2 O1 C9 C10 2.5(2) . . . . ? C7 C8 C9 O1 177.57(12) . . . . ? C7 C8 C9 C10 -1.6(2) . . . . ? O1 C9 C10 C5 -177.51(12) . . . . ? C8 C9 C10 C5 1.6(2) . . . . ? O1 C9 C10 C4 4.1(2) . . . . ? C8 C9 C10 C4 -176.78(12) . . . . ? C6 C5 C10 C9 -0.5(2) . . . . ? C6 C5 C10 C4 177.76(13) . . . . ? C3 C4 C10 C9 -3.6(2) . . . . ? C3 C4 C10 C5 178.16(13) . . . . ? C13 O12 C11 O11 4.6(2) . . . . ? C13 O12 C11 C3 -172.78(11) . . . . ? C4 C3 C11 O11 -167.89(14) . . . . ? C2 C3 C11 O11 11.6(2) . . . . ? C4 C3 C11 O12 9.4(2) . . . . ? C2 C3 C11 O12 -171.06(11) . . . . ? C11 O12 C13 C14 170.5(2) . . . . ? _refine_diff_density_max 0.175 _refine_diff_density_min -0.287 _refine_diff_density_rms 0.072 data_02 # 1. SUBMISSION DETAILS _publ_contact_author ; Itzia I. Padilla-Mart/'inez Departamento de Qu/'imica UPIBI-IPN Av. Acueducto s/n, Col. Barrio la Laguna Ticoman C.P 07340 M/'exico, D. F. ; _publ_contact_author_phone '525 729 6000 EXT 56324' _publ_contact_author_fax '525 729 6000 EXT 56325' _publ_contact_author_email ipadilla@acei.upibi.ipn.mx _publ_requested_journal 'Crystal Growth and Design' _publ_requested_category 'LC' # 3. TITLE AND AUTHOR LIST _publ_section_title ; N-(2-phenylmethyl)-2-R,S)-2-oxo-2H-1-benzopyran-3-carboxamide ; _publ_section_abstract ; The crystallographic study of 3-carboxycoumarins 1-4 and 3-amidocoumarin 5-6 is reported in the context of crystal engineering. The formers can be depicted as two fused rings with opposed polarity which appeared associated through paralled displaced pi-stacking interactions. The benzenoid ring B and the lactone ring L of one molecule interact with the ing L' and benzenoid ring B' of the partner molecule with mean interplanar and mean intercentroid distances ranging between 3.385(6)-3.67(2)A and 3.679(1)-4.081(3)A, respectively. Among the six possible arrangements formed by pairwise overlapping the anti tail-to-tail orientation was the most frequently observed. Pairing through pi-stacking interactions is less favoured when changing the 3-carboxy for a 3-amido group or even annulled increasing the H-bonding capability of the 3-amido group as in 3-oxalamate 6. These fused polar rings can also associate through pi-stacking interactions in the presence of weak interactions such C--H..X(X=O or aromatic ring), as long as these associations do not slip so far the molecular planesto avoid subsequent pi-stacking interactions ; _publ_section_comment ; The supramolecular structure observed in 3-carboxy and 3-amidocoumarins 1-6 is directed by a balance between parallel displaced pi-stacking, weak aryl C-X..pi and strong N-H..O hydrogen bonding interactions. ; loop_ _publ_author_name _publ_author_address ; 'Efr/'en V. Garc/'ia-B/'aez' Departamento de Qu/'imica UPIBI-IPN Av. Acueducto s/n Col. Barrio la Laguna Ticoman C.P. 07340. M/'exico, D. F. ; 'Francisco J. Mart/'inez-Mart/'inez' Departamento de Qu/'imica UPIBI-IPN Av. Acueducto s/n, Col. Barrio la Laguna Ticoman C.P. 07340. M/'exico D. F. ; 'Herbert Hopfl' Centro de Investigaciones Qu/'imicas Universidad Autonoma del Estado de Morelos Cuernavaca Morelos ; _audit_creation_method SHELXL-97 _chemical_name_systematic ; N-(2-phenylmethyl)-2-R,S)-2-oxo-2H-1-benzopyran-3-carboxamide ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C17 H13 N1 O3' _chemical_formula_sum 'C17 H13 N1 O3' _chemical_formula_weight 279.29 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source 'C' 'C' 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 'H' 'H' 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 'N' 'N' 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 'O' 'O' 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Triclinic _symmetry_space_group_name_H-M P-1 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 5.8253(6) _cell_length_b 9.6992(10) _cell_length_c 25.142(3) _cell_angle_alpha 95.038(2) _cell_angle_beta 94.262(2) _cell_angle_gamma 101.515(2) _cell_volume 1380.4(2) _cell_formula_units_Z 4 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used 200 _cell_measurement_theta_min 20 _cell_measurement_theta_max 25 _exptl_crystal_description prism _exptl_crystal_colour colorless _exptl_crystal_size_max 0.30 _exptl_crystal_size_mid 0.16 _exptl_crystal_size_min 0.09 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.344 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 584 _exptl_absorpt_coefficient_mu 0.093 _exptl_absorpt_correction_type none _exptl_absorpt_correction_T_min ? _exptl_absorpt_correction_T_max ? _exptl_absorpt_process_details ? _exptl_special_details ; Diffractometer operator H. Hopfl scanspeed_seconds/frame 10 1200 frames measured in phi (0-360) with chi=0 and om=2th=25 65 frames measured in om (15-35) with chi=280, 2th=29 and phi=0 Crystal mounted in glass fibber ; _diffrn_ambient_temperature 293(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Bruker SMART Area-detector' _diffrn_measurement_method 'phi and omega scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time 0 _diffrn_standards_decay_% ? _diffrn_reflns_number 16116 _diffrn_reflns_av_R_equivalents 0.0538 _diffrn_reflns_av_sigmaI/netI 0.1127 _diffrn_reflns_limit_h_min -7 _diffrn_reflns_limit_h_max 7 _diffrn_reflns_limit_k_min -12 _diffrn_reflns_limit_k_max 12 _diffrn_reflns_limit_l_min -32 _diffrn_reflns_limit_l_max 33 _diffrn_reflns_theta_min 1.63 _diffrn_reflns_theta_max 27.99 _reflns_number_total 6353 _reflns_number_gt 2341 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'SMART (V4.C50)' _computing_cell_refinement 'SMART (V4.C50)' _computing_data_reduction 'SAINT (V4.D50)' _computing_structure_solution 'SHELXS-86 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-93 (Sheldrick, 1993)' _computing_molecular_graphics 'Cameron-WinGx (Farrugia 1997)' _computing_publication_material 'SHELXL (Sheldrick 1997)' _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0496P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment mixed _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 6353 _refine_ls_number_parameters 483 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.1676 _refine_ls_R_factor_gt 0.0467 _refine_ls_wR_factor_ref 0.1158 _refine_ls_wR_factor_gt 0.0910 _refine_ls_goodness_of_fit_ref 0.972 _refine_ls_restrained_S_all 0.972 _refine_ls_shift/su_max 0.039 _refine_ls_shift/su_mean 0.005 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group H4A H 0.834(3) 0.8760(19) 0.5059(7) 0.054(6) Uiso 1 1 d . . . H5A H 0.942(3) 0.7459(19) 0.5808(7) 0.050(6) Uiso 1 1 d . . . H4 H 0.209(3) 0.5894(19) 1.0103(7) 0.047(6) Uiso 1 1 d . . . H8 H 1.065(3) 0.881(2) 1.0663(7) 0.050(6) Uiso 1 1 d . . . H7 H 1.099(4) 0.733(2) 1.1359(8) 0.081(8) Uiso 1 1 d . . . H131 H -0.213(4) 0.732(2) 0.8588(9) 0.083(9) Uiso 1 1 d . . . H5 H 0.425(4) 0.516(2) 1.0899(7) 0.075(7) Uiso 1 1 d . . . H8A H 0.174(4) 0.480(2) 0.5621(8) 0.075(8) Uiso 1 1 d . . . H17A H 0.623(4) 0.878(2) 0.1557(9) 0.082(8) Uiso 1 1 d . . . H19A H 0.250(4) 1.082(2) 0.2569(8) 0.073(7) Uiso 1 1 d . . . H13A H 0.606(5) 1.141(3) 0.3659(10) 0.108(11) Uiso 1 1 d . . . H13B H 0.337(4) 1.114(2) 0.3462(8) 0.078(8) Uiso 1 1 d . . . H19 H 0.258(5) 0.732(3) 0.7781(10) 0.118(11) Uiso 1 1 d . . . H6A H 0.833(4) 0.570(2) 0.6402(8) 0.076(8) Uiso 1 1 d . . . H16A H 0.856(4) 0.845(2) 0.2311(9) 0.081(9) Uiso 1 1 d . . . H18A H 0.325(4) 1.000(2) 0.1702(8) 0.076(8) Uiso 1 1 d . . . H7A H 0.450(3) 0.444(2) 0.6285(8) 0.065(7) Uiso 1 1 d . . . H6 H 0.794(4) 0.559(2) 1.1497(9) 0.083(8) Uiso 1 1 d . . . H12 H 0.267(5) 0.860(3) 0.8846(11) 0.126(12) Uiso 1 1 d . . . H15A H 0.799(4) 0.927(2) 0.3199(9) 0.098(9) Uiso 1 1 d . . . H12A H 0.275(5) 0.899(3) 0.3855(10) 0.120(10) Uiso 1 1 d . . . H15 H -0.369(5) 0.516(3) 0.8072(11) 0.131(12) Uiso 1 1 d . . . H132 H -0.059(4) 0.848(3) 0.8274(10) 0.111(10) Uiso 1 1 d . . . H16 H -0.318(6) 0.339(4) 0.7444(13) 0.175(18) Uiso 1 1 d . . . H17 H 0.004(5) 0.349(3) 0.6939(13) 0.156(14) Uiso 1 1 d . . . H18 H 0.317(8) 0.553(4) 0.7138(16) 0.22(2) Uiso 1 1 d . . . O1A O 0.2373(2) 0.65752(15) 0.49444(6) 0.0602(4) Uani 1 1 d . . . O2A O 0.1283(3) 0.75536(17) 0.42420(7) 0.0770(5) Uani 1 1 d . . . N12A N 0.4363(4) 0.9647(2) 0.38751(7) 0.0642(6) Uani 1 1 d . . . C3A C 0.5244(4) 0.8413(2) 0.46319(8) 0.0487(5) Uani 1 1 d . . . C4A C 0.6837(4) 0.8211(2) 0.50147(9) 0.0505(6) Uani 1 1 d . . . C10A C 0.6297(4) 0.7175(2) 0.53802(8) 0.0480(5) Uani 1 1 d . . . C9A C 0.4025(4) 0.6376(2) 0.53360(9) 0.0518(6) Uani 1 1 d . . . C11A C 0.5943(4) 0.9532(2) 0.42714(9) 0.0553(6) Uani 1 1 d . . . O11A O 0.7889(3) 1.03099(17) 0.43469(6) 0.0796(5) Uani 1 1 d . . . C8A C 0.3319(5) 0.5353(3) 0.56714(11) 0.0636(7) Uani 1 1 d . . . C5A C 0.7893(5) 0.6913(3) 0.57803(10) 0.0612(7) Uani 1 1 d . . . C2A C 0.2888(4) 0.7536(2) 0.45814(9) 0.0552(6) Uani 1 1 d . . . C19A C 0.3873(4) 1.0352(2) 0.25106(10) 0.0595(6) Uani 1 1 d . . . C7A C 0.4949(5) 0.5121(3) 0.60612(11) 0.0686(8) Uani 1 1 d . . . C6A C 0.7238(5) 0.5894(3) 0.61146(11) 0.0674(7) Uani 1 1 d . . . C14A C 0.5225(4) 1.0139(2) 0.29525(9) 0.0525(6) Uani 1 1 d . . . C13A C 0.4796(7) 1.0721(3) 0.35028(10) 0.0738(8) Uani 1 1 d . . . C17A C 0.6011(5) 0.9131(3) 0.19261(12) 0.0701(7) Uani 1 1 d . . . C18A C 0.4253(5) 0.9851(3) 0.20001(11) 0.0692(7) Uani 1 1 d . . . C15A C 0.7012(5) 0.9416(3) 0.28737(12) 0.0738(8) Uani 1 1 d . . . C16A C 0.7386(5) 0.8920(3) 0.23649(13) 0.0799(8) Uani 1 1 d . . . O1 O 0.7257(3) 0.87427(15) 0.99859(6) 0.0623(4) Uani 1 1 d . . . C10 C 0.5447(4) 0.6809(2) 1.04486(8) 0.0482(5) Uani 1 1 d . . . C3 C 0.3327(4) 0.7450(2) 0.96708(8) 0.0504(6) Uani 1 1 d . . . C4 C 0.3425(4) 0.6635(2) 1.00737(9) 0.0533(6) Uani 1 1 d . . . O2 O 0.5540(3) 0.93691(17) 0.92696(6) 0.0779(5) Uani 1 1 d . . . O11 O -0.0567(3) 0.62813(18) 0.93639(6) 0.0749(5) Uani 1 1 d . . . C8 C 0.9412(4) 0.8102(3) 1.07217(10) 0.0647(7) Uani 1 1 d . . . N12 N 0.1268(4) 0.7850(2) 0.88473(8) 0.0705(6) Uani 1 1 d . . . C11 C 0.1180(5) 0.7155(3) 0.92838(9) 0.0579(6) Uani 1 1 d . . . C5 C 0.5648(5) 0.5954(3) 1.08614(9) 0.0586(6) Uani 1 1 d . . . C9 C 0.7361(4) 0.7878(2) 1.03922(8) 0.0509(6) Uani 1 1 d . . . C7 C 0.9580(5) 0.7233(3) 1.11167(11) 0.0676(7) Uani 1 1 d . . . C2 C 0.5355(4) 0.8558(2) 0.96163(9) 0.0579(6) Uani 1 1 d . . . C14 C -0.0506(4) 0.6406(3) 0.79997(9) 0.0606(6) Uani 1 1 d . . . C6 C 0.7697(5) 0.6147(3) 1.11873(10) 0.0637(7) Uani 1 1 d . . . C13 C -0.0647(6) 0.7587(4) 0.84231(12) 0.0808(9) Uani 1 1 d . . . C19 C 0.1404(6) 0.6500(4) 0.77086(13) 0.0875(9) Uani 1 1 d . . . C15 C -0.2224(6) 0.5187(4) 0.78973(13) 0.0873(9) Uani 1 1 d . . . C18 C 0.1643(7) 0.5476(5) 0.73263(14) 0.1075(11) Uani 1 1 d . . . C17 C -0.0055(9) 0.4284(5) 0.72258(15) 0.1065(12) Uani 1 1 d . . . C16 C -0.1973(9) 0.4119(4) 0.75055(17) 0.1095(13) Uani 1 1 d . . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 O1A 0.0507(10) 0.0578(10) 0.0658(10) 0.0069(8) 0.0103(8) -0.0057(8) O2A 0.0571(11) 0.0841(12) 0.0813(12) 0.0136(10) -0.0096(10) -0.0022(9) N12A 0.0757(16) 0.0650(14) 0.0482(12) 0.0085(11) -0.0007(12) 0.0073(12) C3A 0.0457(14) 0.0430(13) 0.0537(14) 0.0006(11) 0.0063(12) 0.0019(11) C4A 0.0461(15) 0.0431(14) 0.0593(16) 0.0047(12) 0.0092(12) 0.0009(12) C10A 0.0482(14) 0.0431(13) 0.0522(14) 0.0039(11) 0.0110(12) 0.0066(11) C9A 0.0505(15) 0.0458(14) 0.0575(15) -0.0017(12) 0.0140(12) 0.0060(12) C11A 0.0655(17) 0.0459(14) 0.0517(15) 0.0036(12) 0.0066(13) 0.0051(13) O11A 0.0684(11) 0.0718(11) 0.0885(13) 0.0329(9) -0.0051(9) -0.0153(10) C8A 0.0691(19) 0.0503(15) 0.0685(18) 0.0069(14) 0.0282(15) -0.0027(15) C5A 0.0579(17) 0.0568(16) 0.0677(17) 0.0111(14) 0.0120(14) 0.0048(14) C2A 0.0571(17) 0.0515(15) 0.0540(15) -0.0004(12) 0.0109(13) 0.0049(13) C19A 0.0621(17) 0.0641(16) 0.0545(17) 0.0053(13) 0.0057(13) 0.0190(13) C7A 0.091(2) 0.0512(16) 0.0689(19) 0.0169(15) 0.0299(17) 0.0151(16) C6A 0.075(2) 0.0635(18) 0.0695(19) 0.0189(15) 0.0163(16) 0.0202(16) C14A 0.0583(15) 0.0448(13) 0.0517(15) 0.0071(11) 0.0002(12) 0.0057(11) C13A 0.104(3) 0.0645(19) 0.0530(18) 0.0049(15) -0.0015(17) 0.0208(19) C17A 0.086(2) 0.0647(18) 0.063(2) 0.0077(15) 0.0205(17) 0.0177(15) C18A 0.082(2) 0.0717(18) 0.0568(18) 0.0074(14) -0.0005(16) 0.0248(15) C15A 0.0729(19) 0.085(2) 0.066(2) 0.0106(16) -0.0048(16) 0.0262(16) C16A 0.069(2) 0.085(2) 0.094(3) 0.0108(18) 0.0205(18) 0.0317(16) O1 0.0608(11) 0.0650(10) 0.0569(10) 0.0118(9) 0.0086(8) -0.0002(8) C10 0.0515(15) 0.0434(13) 0.0468(14) 0.0022(11) 0.0076(11) 0.0035(12) C3 0.0610(15) 0.0453(14) 0.0443(14) 0.0017(11) 0.0104(11) 0.0085(12) C4 0.0546(16) 0.0498(15) 0.0522(15) 0.0028(12) 0.0083(12) 0.0027(13) O2 0.0891(13) 0.0743(12) 0.0662(11) 0.0266(10) 0.0112(9) -0.0024(9) O11 0.0634(11) 0.0811(12) 0.0735(11) 0.0131(9) -0.0037(9) 0.0008(10) C8 0.0492(17) 0.0751(19) 0.0659(18) 0.0028(15) 0.0125(14) 0.0034(15) N12 0.0842(17) 0.0730(15) 0.0536(14) 0.0112(12) -0.0021(12) 0.0157(13) C11 0.0713(18) 0.0536(15) 0.0491(15) 0.0033(13) 0.0051(14) 0.0150(14) C5 0.0631(17) 0.0558(16) 0.0569(16) 0.0061(13) 0.0074(14) 0.0116(14) C9 0.0534(15) 0.0557(15) 0.0450(14) 0.0056(12) 0.0117(12) 0.0123(12) C7 0.0582(18) 0.085(2) 0.0614(18) 0.0029(15) 0.0032(15) 0.0209(16) C2 0.0670(17) 0.0548(15) 0.0518(15) 0.0049(13) 0.0157(14) 0.0089(13) C14 0.0620(17) 0.0710(18) 0.0503(15) 0.0210(14) -0.0030(13) 0.0141(15) C6 0.0686(19) 0.0635(17) 0.0606(17) 0.0074(14) 0.0049(15) 0.0176(15) C13 0.086(2) 0.094(2) 0.068(2) 0.0197(19) -0.0041(18) 0.0328(19) C19 0.080(2) 0.098(3) 0.078(2) 0.0002(19) 0.0135(17) 0.001(2) C15 0.072(2) 0.107(3) 0.077(2) 0.025(2) 0.0010(17) -0.002(2) C18 0.106(3) 0.131(3) 0.083(2) -0.006(2) 0.014(2) 0.024(3) C17 0.151(4) 0.097(3) 0.075(3) 0.006(2) -0.013(3) 0.044(3) C16 0.135(4) 0.081(3) 0.092(3) 0.022(2) -0.028(3) -0.018(3) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag O1A C2A 1.367(2) . ? O1A C9A 1.379(2) . ? O2A C2A 1.222(2) . ? N12A C11A 1.333(3) . ? N12A C13A 1.458(3) . ? N12A H12A 1.02(3) . ? C3A C4A 1.341(3) . ? C3A C2A 1.453(3) . ? C3A C11A 1.488(3) . ? C4A C10A 1.426(3) . ? C4A H4A 0.922(19) . ? C10A C9A 1.385(3) . ? C10A C5A 1.393(3) . ? C9A C8A 1.378(3) . ? C11A O11A 1.221(2) . ? C8A C7A 1.378(3) . ? C8A H8A 0.96(2) . ? C5A C6A 1.368(3) . ? C5A H5A 0.933(18) . ? C19A C14A 1.368(3) . ? C19A C18A 1.381(3) . ? C19A H19A 1.01(2) . ? C7A C6A 1.384(3) . ? C7A H7A 0.92(2) . ? C6A H6A 0.98(2) . ? C14A C15A 1.383(3) . ? C14A C13A 1.506(3) . ? C13A H13A 0.92(3) . ? C13A H13B 0.99(2) . ? C17A C18A 1.364(3) . ? C17A C16A 1.369(3) . ? C17A H17A 0.99(2) . ? C18A H18A 0.96(2) . ? C15A C16A 1.375(3) . ? C15A H15A 1.00(2) . ? C16A H16A 0.91(2) . ? O1 C2 1.364(2) . ? O1 C9 1.383(2) . ? C10 C9 1.388(3) . ? C10 C5 1.396(3) . ? C10 C4 1.425(3) . ? C3 C4 1.343(3) . ? C3 C2 1.454(3) . ? C3 C11 1.490(3) . ? C4 H4 0.959(19) . ? O2 C2 1.221(2) . ? O11 C11 1.229(3) . ? C8 C7 1.368(3) . ? C8 C9 1.371(3) . ? C8 H8 0.920(19) . ? N12 C11 1.336(3) . ? N12 C13 1.452(3) . ? N12 H12 0.98(3) . ? C5 C6 1.368(3) . ? C5 H5 1.02(2) . ? C7 C6 1.395(3) . ? C7 H7 0.97(2) . ? C14 C19 1.369(3) . ? C14 C15 1.379(4) . ? C14 C13 1.513(4) . ? C6 H6 1.00(2) . ? C13 H131 0.98(2) . ? C13 H132 0.97(3) . ? C19 C18 1.355(4) . ? C19 H19 0.93(3) . ? C15 C16 1.403(5) . ? C15 H15 0.98(3) . ? C18 C17 1.354(5) . ? C18 H18 1.03(4) . ? C17 C16 1.354(5) . ? C17 H17 1.02(3) . ? C16 H16 0.88(4) . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C2A O1A C9A 122.41(18) . . ? C11A N12A C13A 123.0(3) . . ? C11A N12A H12A 117.2(15) . . ? C13A N12A H12A 119.7(15) . . ? C4A C3A C2A 119.1(2) . . ? C4A C3A C11A 118.9(2) . . ? C2A C3A C11A 122.0(2) . . ? C3A C4A C10A 122.3(2) . . ? C3A C4A H4A 121.0(12) . . ? C10A C4A H4A 116.7(12) . . ? C9A C10A C5A 117.7(2) . . ? C9A C10A C4A 117.8(2) . . ? C5A C10A C4A 124.6(2) . . ? C8A C9A O1A 117.3(2) . . ? C8A C9A C10A 122.3(3) . . ? O1A C9A C10A 120.4(2) . . ? O11A C11A N12A 122.5(2) . . ? O11A C11A C3A 120.2(2) . . ? N12A C11A C3A 117.4(2) . . ? C7A C8A C9A 118.3(3) . . ? C7A C8A H8A 121.7(13) . . ? C9A C8A H8A 119.9(13) . . ? C6A C5A C10A 121.0(3) . . ? C6A C5A H5A 121.9(12) . . ? C10A C5A H5A 117.0(11) . . ? O2A C2A O1A 115.3(2) . . ? O2A C2A C3A 126.8(2) . . ? O1A C2A C3A 117.9(2) . . ? C14A C19A C18A 121.4(2) . . ? C14A C19A H19A 118.1(11) . . ? C18A C19A H19A 120.3(11) . . ? C8A C7A C6A 120.9(3) . . ? C8A C7A H7A 119.2(13) . . ? C6A C7A H7A 119.9(13) . . ? C5A C6A C7A 119.8(3) . . ? C5A C6A H6A 122.1(13) . . ? C7A C6A H6A 118.1(13) . . ? C19A C14A C15A 118.0(2) . . ? C19A C14A C13A 120.1(2) . . ? C15A C14A C13A 121.9(2) . . ? N12A C13A C14A 113.3(2) . . ? N12A C13A H13A 106.7(16) . . ? C14A C13A H13A 111.8(16) . . ? N12A C13A H13B 107.9(13) . . ? C14A C13A H13B 107.4(13) . . ? H13A C13A H13B 110(2) . . ? C18A C17A C16A 118.9(3) . . ? C18A C17A H17A 118.3(13) . . ? C16A C17A H17A 122.8(13) . . ? C17A C18A C19A 120.2(3) . . ? C17A C18A H18A 120.9(13) . . ? C19A C18A H18A 118.9(13) . . ? C16A C15A C14A 120.4(3) . . ? C16A C15A H15A 122.5(13) . . ? C14A C15A H15A 117.1(13) . . ? C17A C16A C15A 121.0(3) . . ? C17A C16A H16A 118.3(15) . . ? C15A C16A H16A 120.7(15) . . ? C2 O1 C9 122.50(18) . . ? C9 C10 C5 117.9(2) . . ? C9 C10 C4 117.8(2) . . ? C5 C10 C4 124.3(2) . . ? C4 C3 C2 118.8(2) . . ? C4 C3 C11 119.0(2) . . ? C2 C3 C11 122.2(2) . . ? C3 C4 C10 122.6(2) . . ? C3 C4 H4 118.3(11) . . ? C10 C4 H4 119.1(11) . . ? C7 C8 C9 118.7(3) . . ? C7 C8 H8 122.1(12) . . ? C9 C8 H8 119.2(12) . . ? C11 N12 C13 122.6(3) . . ? C11 N12 H12 115.2(17) . . ? C13 N12 H12 122.1(17) . . ? O11 C11 N12 122.2(2) . . ? O11 C11 C3 120.4(2) . . ? N12 C11 C3 117.3(2) . . ? C6 C5 C10 120.6(3) . . ? C6 C5 H5 121.7(11) . . ? C10 C5 H5 117.7(11) . . ? C8 C9 O1 117.7(2) . . ? C8 C9 C10 122.3(2) . . ? O1 C9 C10 120.0(2) . . ? C8 C7 C6 120.8(3) . . ? C8 C7 H7 122.5(14) . . ? C6 C7 H7 116.7(14) . . ? O2 C2 O1 115.4(2) . . ? O2 C2 C3 126.4(2) . . ? O1 C2 C3 118.2(2) . . ? C19 C14 C15 117.1(3) . . ? C19 C14 C13 120.4(3) . . ? C15 C14 C13 122.6(3) . . ? C5 C6 C7 119.7(3) . . ? C5 C6 H6 124.3(13) . . ? C7 C6 H6 115.8(13) . . ? N12 C13 C14 113.4(2) . . ? N12 C13 H131 107.8(13) . . ? C14 C13 H131 108.0(14) . . ? N12 C13 H132 105.7(16) . . ? C14 C13 H132 111.9(15) . . ? H131 C13 H132 110(2) . . ? C18 C19 C14 123.2(3) . . ? C18 C19 H19 119.5(17) . . ? C14 C19 H19 117.3(17) . . ? C14 C15 C16 119.9(3) . . ? C14 C15 H15 117.5(18) . . ? C16 C15 H15 122.2(18) . . ? C17 C18 C19 119.4(4) . . ? C17 C18 H18 119(2) . . ? C19 C18 H18 122(2) . . ? C18 C17 C16 120.2(4) . . ? C18 C17 H17 122(2) . . ? C16 C17 H17 118(2) . . ? C17 C16 C15 120.2(4) . . ? C17 C16 H16 124(2) . . ? C15 C16 H16 115(2) . . ? _diffrn_measured_fraction_theta_max 0.952 _diffrn_reflns_theta_full 27.99 _diffrn_measured_fraction_theta_full 0.952 _refine_diff_density_max 0.124 _refine_diff_density_min -0.149 _refine_diff_density_rms 0.032 data_03 # 1. SUBMISSION DETAILS _publ_contact_author ; Itzia I. Padilla-Mart/'inez Departamento de Qu/'imica UPIBI-IPN Av. Acueducto s/n, Col. Barrio la Laguna Ticoman C.P 07340 M/'exico, D. F. ; _publ_contact_author_phone '525 729 6000 EXT 56324' _publ_contact_author_fax '525 729 6000 EXT 56325' _publ_contact_author_email ipadilla@acei.upibi.ipn.mx _publ_requested_journal 'Crystal Growth and Design' _publ_requested_category 'LC' # 3. TITLE AND AUTHOR LIST _publ_section_title ; N-[1-(R,S)-((2H-1-benzopyran-2-oxo-3-yl)carboxyl)methyl]benzylamide ; _publ_section_abstract ; The crystallographic study of 3-carboxycoumarins 1-4 and 3-amidocoumarin 5-6 is reported in the context of crystal engineering. The formers can be depicted as two fused rings with opposed polarity which appeared associated through paralled displaced pi-stacking interactions. The benzenoid ring B and the lactone ring L of one molecule interact with the ing L' and benzenoid ring B' of the partner molecule with mean interplanar and mean intercentroid distances ranging between 3.385(6)-3.67(2)A and 3.679(1)-4.081(3)A, respectively. Among the six possible arrangements formed by pairwise overlapping the anti tail-to-tail orientation was the most frequently observed. Pairing through pi-stacking interactions is less favo ured when changing the 3-carboxy for a 3-amido group or even annulled increasing the H-bonding capability of the 3-amido group as in 3-oxalamate 6. These fused polar rings can also associate through pi-stacking interactions in the presence of weak interactions such C--H..X(X=O or aromatic ring), as long as these associations do not slip so far the molecular planes to avoid subsequent pi-stacking interactions ; _publ_section_comment ; The supramolecular structure observed in 3-carboxy and 3-amidocoumarins 1-6 is directed by a balance between parallel displaced pi-stacking, weak aryl C-X..pi and strong N-H..O hydrogen bonding interactions. ; loop_ _publ_author_name _publ_author_address ; 'Efr/'en V. Garc/'ia-B/'aez' Departamento de Qu/'imica UPIBI-IPN Av. Acueducto s/n Col. Barrio la Laguna Ticoman C.P. 07340. M/'exico, D. F. ; 'Francisco J. Mart/'inez-Mart/'inez' Departamento de Qu/'imica UPIBI-IPN Av. Acueducto s/n, Col. Barrio la Laguna Ticoman C.P. 07340. M/'exico D. F. ; 'Herbert Hopfl' Centro de Investigaciones Qu/'imicas Universidad Autonoma del Estado de Morelos Cuernavaca Morelos ; _audit_creation_method SHELXL-97 _chemical_name_systematic ; N-[1-(R,S)-((2H-1-benzopyran-2-oxo-3-yl)carboxyl)methyl]benzylamide ; _chemical_name_common ? _chemical_formula_moiety ? _chemical_formula_structural ? _chemical_formula_analytical 'C18 H15 N O3' _chemical_formula_sum 'C18 H15 N O3' _chemical_formula_weight 293.31 _chemical_melting_point ? _chemical_compound_source ? _symmetry_cell_setting Triclinic _symmetry_space_group_name_Hall '-P 1' _symmetry_space_group_name_H-M 'P -1' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source 'C' 'C' 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 'H' 'H' 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 'N' 'N' 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 'O' 'O' 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _cell_length_a 5.8914(6) _cell_length_b 7.9956(9) _cell_length_c 16.114(2) _cell_angle_alpha 98.317(2) _cell_angle_beta 92.667(2) _cell_angle_gamma 102.673(2) _cell_volume 730.37(14) _cell_formula_units_Z 2 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used 200 _cell_measurement_theta_min 20 _cell_measurement_theta_max 25 _exptl_crystal_description prism _exptl_crystal_colour colorless _exptl_crystal_size_max 0.4 _exptl_crystal_size_mid 0.3 _exptl_crystal_size_min 0.3 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.334 _exptl_crystal_density_method ? _exptl_crystal_F_000 308 _exptl_absorpt_coefficient_mu 0.091 _exptl_absorpt_correction_type none _exptl_absorpt_correction_T_min ? _exptl_absorpt_correction_T_max ? _exptl_special_details ; Diffractometer operator H. Hopfl scanspeed_seconds/frame 10 1200 frames measured in phi (0-360) with chi=0 and om=2th=25 65 frames measured in om (15-35) with chi=280, 2th=29 and phi=0 Crystal mounted in glass fibber ; _diffrn_ambient_temperature 293(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device 'Bruker SMART Area-detector' _diffrn_measurement_method 'phi and omega scans' _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% 0 _diffrn_reflns_number 8340 _diffrn_reflns_av_R_equivalents 0.0646 _diffrn_reflns_av_sigmaI/netI 0.0594 _diffrn_reflns_limit_h_min -7 _diffrn_reflns_limit_h_max 7 _diffrn_reflns_limit_k_min -10 _diffrn_reflns_limit_k_max 10 _diffrn_reflns_limit_l_min -20 _diffrn_reflns_limit_l_max 20 _diffrn_reflns_theta_min 1.28 _diffrn_reflns_theta_max 27.53 _reflns_number_total 3279 _reflns_number_gt 2107 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'SMART (V4.C50)' _computing_cell_refinement 'SMART (V4.C50)' _computing_data_reduction 'SAINT (V4.D50)' _computing_structure_solution 'SHELXS-86 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-93 (Sheldrick, 1993)' _computing_molecular_graphics 'Cameron-WinGx (Farrugia 1997)' _computing_publication_material 'SHELXL (Sheldrick 1997)' _refine_special_details ; Refinement on F^2^ for ALL reflections except for 0 with very negative F^2^ or flagged by the user for potential systematic errors. Weighted R-factors wR and all goodnesses of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The observed criterion of F^2^ > 2sigma(F^2^) is used only for calculating _R_factor_obs etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.1316P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary 'direct methods' _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geometrically _refine_ls_hydrogen_treatment mixed _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 3279 _refine_ls_number_parameters 259 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.1107 _refine_ls_R_factor_gt 0.0784 _refine_ls_wR_factor_all 0.2345 _refine_ls_wR_factor_ref 0.2148 _refine_ls_goodness_of_fit_all 1.036 _refine_ls_goodness_of_fit_ref 1.201 _refine_ls_restrained_S_all 1.036 _refine_ls_restrained_S_ref 1.201 _refine_ls_shift/su_max -0.001 _refine_ls_shift/esd_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_thermal_displace_type _atom_site_occupancy _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_group N12 N 0.7443(4) 0.8434(3) 0.21026(12) 0.0451(5) Uani 1 d . . O1 O 0.6822(3) 0.6650(3) 0.44573(11) 0.0601(6) Uani 1 d . . O11 O 1.1341(3) 0.9147(3) 0.23722(11) 0.0630(6) Uani 1 d . . O2 O 0.5054(3) 0.6663(3) 0.32370(12) 0.0704(7) Uani 1 d . . C3 C 0.9123(4) 0.8005(3) 0.34316(14) 0.0416(6) Uani 1 d . . C11 C 0.9400(4) 0.8584(3) 0.25865(14) 0.0438(6) Uani 1 d . . C10 C 1.0910(4) 0.7875(3) 0.48082(15) 0.0470(6) Uani 1 d . . C4 C 1.1015(5) 0.8345(3) 0.3979(2) 0.0492(6) Uani 1 d . . C9 C 0.8761(4) 0.7041(3) 0.50258(15) 0.0489(6) Uani 1 d . . C14 C 0.7886(4) 1.0827(3) 0.12722(13) 0.0413(6) Uani 1 d . . C2 C 0.6890(5) 0.7088(3) 0.3664(2) 0.0499(6) Uani 1 d . . C13 C 0.7440(5) 0.8879(3) 0.12526(14) 0.0444(6) Uani 1 d . . C19 C 0.6310(5) 1.1755(3) 0.15864(15) 0.0500(6) Uani 1 d . . C8 C 0.8443(6) 0.6559(4) 0.5808(2) 0.0648(8) Uani 1 d . . C5 C 1.2806(5) 0.8211(4) 0.5411(2) 0.0611(7) Uani 1 d . . C15 C 0.9877(5) 1.1682(3) 0.0959(2) 0.0545(7) Uani 1 d . . C7 C 1.0323(6) 0.6938(4) 0.6393(2) 0.0662(8) Uani 1 d . . C17 C 0.8735(7) 1.4372(4) 0.1277(2) 0.0720(9) Uani 1 d . . C18 C 0.6770(6) 1.3545(4) 0.1594(2) 0.0644(8) Uani 1 d . . C6 C 1.2493(6) 0.7747(4) 0.6193(2) 0.0665(8) Uani 1 d . . C16 C 1.0288(6) 1.3452(4) 0.0959(2) 0.0696(9) Uani 1 d . . C20 C 0.5168(6) 0.7914(4) 0.0765(2) 0.0619(8) Uani 1 d . . H12A H 0.6146(46) 0.8086(35) 0.2295(16) 0.048(7) Uiso 1 d . . H20A H 0.3698(56) 0.8072(44) 0.1022(22) 0.085(11) Uiso 1 d . . H4A H 1.2491(50) 0.8866(39) 0.3829(17) 0.062(8) Uiso 1 d . . H13A H 0.8852(43) 0.8492(35) 0.1002(16) 0.054(7) Uiso 1 d . . H5A H 1.4411(53) 0.8717(39) 0.5260(18) 0.068(8) Uiso 1 d . . H8A H 0.6986(57) 0.6131(44) 0.5916(20) 0.076(10) Uiso 1 d . . H16A H 1.1602(56) 1.3999(43) 0.0737(20) 0.079(10) Uiso 1 d . . H19A H 0.4894(47) 1.1172(35) 0.1815(16) 0.052(7) Uiso 1 d . . H20B H 0.5085(46) 0.8133(38) 0.0221(20) 0.064(8) Uiso 1 d . . H18A H 0.5638(50) 1.4167(41) 0.1793(19) 0.068(9) Uiso 1 d . . H6A H 1.3848(54) 0.7978(40) 0.6564(19) 0.068(8) Uiso 1 d . . H7A H 0.9983(55) 0.6630(41) 0.6932(20) 0.077(9) Uiso 1 d . . H17A H 0.9074(52) 1.5535(46) 0.1295(20) 0.078(9) Uiso 1 d . . H15A H 1.1059(49) 1.1075(39) 0.0758(17) 0.060(8) Uiso 1 d . . H20C H 0.5084(55) 0.6679(46) 0.0685(20) 0.078(9) Uiso 1 d . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 N12 0.0511(12) 0.0430(11) 0.0409(11) 0.0125(9) 0.0038(10) 0.0059(9) O1 0.0550(11) 0.0729(13) 0.0504(11) 0.0244(9) 0.0016(8) 0.0014(9) O11 0.0573(12) 0.0775(14) 0.0542(11) 0.0247(10) 0.0069(9) 0.0057(10) O2 0.0517(11) 0.095(2) 0.0609(12) 0.0324(11) -0.0043(9) -0.0020(10) C3 0.0510(14) 0.0344(12) 0.0384(12) 0.0058(9) 0.0018(10) 0.0082(10) C11 0.0495(14) 0.0385(12) 0.0423(13) 0.0069(10) 0.0028(10) 0.0078(10) C10 0.0559(15) 0.0430(13) 0.0413(12) 0.0044(10) 0.0017(11) 0.0115(11) C4 0.0501(15) 0.0493(14) 0.0458(13) 0.0081(11) 0.0057(11) 0.0056(11) C9 0.057(2) 0.0472(14) 0.0421(13) 0.0106(11) 0.0009(11) 0.0094(11) C14 0.0509(13) 0.0364(12) 0.0344(11) 0.0061(9) -0.0057(9) 0.0069(10) C2 0.0535(15) 0.0515(14) 0.0453(13) 0.0155(11) 0.0032(11) 0.0086(12) C13 0.060(2) 0.0345(12) 0.0365(12) 0.0068(9) -0.0013(11) 0.0061(11) C19 0.057(2) 0.0522(15) 0.0399(13) 0.0052(11) -0.0023(11) 0.0141(13) C8 0.073(2) 0.071(2) 0.052(2) 0.0235(14) 0.0097(15) 0.011(2) C5 0.060(2) 0.071(2) 0.0491(15) 0.0090(13) -0.0023(13) 0.0104(14) C15 0.059(2) 0.0432(14) 0.060(2) 0.0104(12) 0.0040(13) 0.0073(12) C7 0.088(2) 0.072(2) 0.0414(15) 0.0164(14) 0.0010(14) 0.020(2) C17 0.104(3) 0.0333(15) 0.073(2) 0.0052(14) -0.012(2) 0.009(2) C18 0.086(2) 0.055(2) 0.055(2) -0.0007(13) -0.0099(15) 0.032(2) C6 0.076(2) 0.075(2) 0.048(2) 0.0076(14) -0.0103(14) 0.019(2) C16 0.074(2) 0.047(2) 0.083(2) 0.0185(15) 0.004(2) -0.0028(15) C20 0.082(2) 0.045(2) 0.048(2) 0.0067(12) -0.0135(15) -0.0057(14) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag N12 C11 1.334(3) . ? N12 C13 1.464(3) . ? N12 H12A 0.84(3) . ? O1 C2 1.374(3) . ? O1 C9 1.380(3) . ? O11 C11 1.219(3) . ? O2 C2 1.209(3) . ? C3 C4 1.342(3) . ? C3 C2 1.452(3) . ? C3 C11 1.505(3) . ? C10 C9 1.382(4) . ? C10 C5 1.398(4) . ? C10 C4 1.440(3) . ? C4 H4A 0.94(3) . ? C9 C8 1.379(3) . ? C14 C15 1.378(3) . ? C14 C19 1.381(4) . ? C14 C13 1.518(3) . ? C13 C20 1.509(4) . ? C13 H13A 1.03(3) . ? C19 C18 1.395(4) . ? C19 H19A 0.98(3) . ? C8 C7 1.371(4) . ? C8 H8A 0.89(3) . ? C5 C6 1.374(4) . ? C5 H5A 1.00(3) . ? C15 C16 1.382(4) . ? C15 H15A 0.97(3) . ? C7 C6 1.375(5) . ? C7 H7A 0.95(3) . ? C17 C18 1.362(5) . ? C17 C16 1.368(5) . ? C17 H17A 0.90(3) . ? C18 H18A 0.96(3) . ? C6 H6A 0.94(3) . ? C16 H16A 0.92(3) . ? C20 H20A 1.00(3) . ? C20 H20B 0.92(3) . ? C20 H20C 0.97(3) . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C11 N12 C13 122.9(2) . . ? C11 N12 H12A 119.0(17) . . ? C13 N12 H12A 118.1(17) . . ? C2 O1 C9 122.9(2) . . ? C4 C3 C2 119.7(2) . . ? C4 C3 C11 118.3(2) . . ? C2 C3 C11 122.0(2) . . ? O11 C11 N12 123.2(2) . . ? O11 C11 C3 120.1(2) . . ? N12 C11 C3 116.7(2) . . ? C9 C10 C5 117.6(2) . . ? C9 C10 C4 117.3(2) . . ? C5 C10 C4 125.1(2) . . ? C3 C4 C10 122.3(2) . . ? C3 C4 H4A 121.1(17) . . ? C10 C4 H4A 116.6(17) . . ? C8 C9 O1 117.0(2) . . ? C8 C9 C10 122.4(2) . . ? O1 C9 C10 120.6(2) . . ? C15 C14 C19 119.4(2) . . ? C15 C14 C13 119.6(2) . . ? C19 C14 C13 121.0(2) . . ? O2 C2 O1 115.4(2) . . ? O2 C2 C3 127.4(2) . . ? O1 C2 C3 117.3(2) . . ? N12 C13 C20 108.8(2) . . ? N12 C13 C14 111.5(2) . . ? C20 C13 C14 112.7(2) . . ? N12 C13 H13A 105.0(14) . . ? C20 C13 H13A 112.0(15) . . ? C14 C13 H13A 106.6(14) . . ? C14 C19 C18 119.6(3) . . ? C14 C19 H19A 120.5(16) . . ? C18 C19 H19A 119.8(16) . . ? C7 C8 C9 118.8(3) . . ? C7 C8 H8A 124.1(20) . . ? C9 C8 H8A 116.7(20) . . ? C6 C5 C10 120.2(3) . . ? C6 C5 H5A 119.8(16) . . ? C10 C5 H5A 119.9(16) . . ? C14 C15 C16 120.3(3) . . ? C14 C15 H15A 121.4(16) . . ? C16 C15 H15A 118.3(17) . . ? C8 C7 C6 120.4(3) . . ? C8 C7 H7A 115.1(19) . . ? C6 C7 H7A 124.6(19) . . ? C18 C17 C16 120.1(3) . . ? C18 C17 H17A 121.1(20) . . ? C16 C17 H17A 118.8(20) . . ? C17 C18 C19 120.4(3) . . ? C17 C18 H18A 120.6(17) . . ? C19 C18 H18A 118.9(18) . . ? C5 C6 C7 120.7(3) . . ? C5 C6 H6A 115.9(18) . . ? C7 C6 H6A 123.4(18) . . ? C17 C16 C15 120.2(3) . . ? C17 C16 H16A 120.4(21) . . ? C15 C16 H16A 119.3(21) . . ? C13 C20 H20A 116.8(20) . . ? C13 C20 H20B 112.4(18) . . ? H20A C20 H20B 108.6(25) . . ? C13 C20 H20C 109.8(19) . . ? H20A C20 H20C 105.8(27) . . ? H20B C20 H20C 102.4(26) . . ? _refine_diff_density_max 0.315 _refine_diff_density_min -0.258 _refine_diff_density_rms 0.061 data_04 # 1. SUBMISSION DETAILS _publ_contact_author ; Itzia I. Padilla-Mart/'inez Departamento de Qu/'imica UPIBI-IPN Av. Acueducto s/n, Col. Barrio la Laguna Ticoman C.P 07340 M/'exico, D. F. ; _publ_contact_author_phone '525 729 6000 EXT 56324' _publ_contact_author_fax '525 729 6000 EXT 56325' _publ_contact_author_email ipadilla@acei.upibi.ipn.mx _publ_requested_journal 'Crystal Growth and Design' _publ_requested_category 'LC' # 3. TITLE AND AUTHOR LIST _publ_section_title ; N-[(2H-1-benzopyran-2-oxo-3-yl)carboxyl]piperidimide ; _publ_section_abstract ; The crystallographic study of 3-carboxycoumarins 1-4 and 3-amidocoumarin 5-6 is reported in the context of crystal engineering. The formers can be depicted as two fused rings with opposed polarity which appeared associated through paralled displaced pi-stacking interactions. The benzenoid ring B and the lactone ring L of one molecule interact with the ing L' and benzenoid ring B' of the partner molecule with mean interplanar and mean intercentroid distances ranging between 3.385(6)-3.67(2)A and 3.679(1)-4.081(3)A, respectively. Among the six possible arrangements formed by pairwise overlapping the anti tail-to-tail orientation was the most frequently observed. Pairing through pi-stacking interactions is less favoured when changing the 3-carboxy for a 3-amido group or even annulled increasing the H-bonding capability of the 3-amido group as in 3-oxalamate 6. These fused polar rings can also associate through pi-stacking interactions in the presence of weak interactions such C--H..X(X=O or aromatic ring), as long as these associations do not slip so far the molecular planeshto avoid subsequent pi-stacking interactions ; _publ_section_comment ; The supramolecular structure observed in 3-carboxy and 3-amidocoumarins 1-6 is directed by a balance between parallel displaced pi-stacking, weak aryl C-X..pi and strong N-H..O hydrogen bonding interactions. ; loop_ _publ_author_name _publ_author_address ; 'Efr/'en V. Garc/'ia-B/'aez' Departamento de Qu/'imica UPIBI-IPN Av. Acueducto s/n Col. Barrio la Laguna Ticoman C.P. 07340. M/'exico, D. F. ; 'Francisco J. Mart/'inez-Mart/'inez' Departamento de Qu/'imica UPIBI-IPN Av. Acueducto s/n, Col. Barrio la Laguna Ticoman C.P. 07340. M/'exico D. F. ; 'Herbert Hopfl' Centro de Investigaciones Qu/'imicas Universidad Autonoma del Estado de Morelos Cuernavaca Morelos ; _chemical_name_common ? _chemical_formula_moiety ? _chemical_formula_structural ? _chemical_formula_analytical 'C15 H15 N O3' _chemical_formula_sum 'C15 H15 N O3' _chemical_formula_weight 257.28 _chemical_melting_point ? _chemical_compound_source ? loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source 'C' 'C' 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 'H' 'H' 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 'N' 'N' 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 'O' 'O' 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Monoclinic _symmetry_space_group_name_H-M C2/c loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y, -z+1/2' 'x+1/2, y+1/2, z' '-x+1/2, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y, z-1/2' '-x+1/2, -y+1/2, -z' 'x+1/2, -y+1/2, z-1/2' _cell_length_a 16.509(4) _cell_length_b 8.732(2) _cell_length_c 18.498(4) _cell_angle_alpha 90.00 _cell_angle_beta 103.301(4) _cell_angle_gamma 90.00 _cell_volume 2595.2(10) _cell_formula_units_Z 8 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used 200 _cell_measurement_theta_min 20 _cell_measurement_theta_max 25 _exptl_crystal_description prism _exptl_crystal_colour colorless _exptl_crystal_size_max 0.5 _exptl_crystal_size_mid 0.3 _exptl_crystal_size_min 0.2 _exptl_crystal_density_diffrn 1.317 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1088 _exptl_absorpt_coefficient_mu 0.092 _exptl_absorpt_correction_type none _exptl_absorpt_correction_T_min ? _exptl_absorpt_correction_T_max ? _exptl_special_details ; Diffractometer operator H. Hopfl scanspeed_seconds/frame 10 1200 frames measured in phi (0-360) with chi=0 and om=2th=25 65 frames measured in om (15-35) with chi=280, 2th=29 and phi=0 Crystal mounted in glass fibber ; _diffrn_ambient_temperature 293(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device 'Bruker SMART Area-detector' _diffrn_measurement_method 'phi and omega scans' _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% 0 _diffrn_reflns_number 8230 _diffrn_reflns_av_R_equivalents 0.1195 _diffrn_reflns_av_sigmaI/netI 0.1384 _diffrn_reflns_limit_h_min -20 _diffrn_reflns_limit_h_max 14 _diffrn_reflns_limit_k_min -10 _diffrn_reflns_limit_k_max 10 _diffrn_reflns_limit_l_min -21 _diffrn_reflns_limit_l_max 22 _diffrn_reflns_theta_min 2.26 _reflns_number_total 2592 _diffrn_reflns_theta_max 26.21 _diffrn_reflns_theta_full 26.21 _diffrn_measured_fraction_theta_full 0.991 _diffrn_measured_fraction_theta_max 0.991 _reflns_number_gt 1253 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'SMART (V4.C50)' _computing_cell_refinement 'SMART (V4.C50)' _computing_data_reduction 'SAINT (V4.D50)' _computing_structure_solution 'SHELXS-86 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-93 (Sheldrick, 1993)' _computing_molecular_graphics 'Cameron-WinGx (Farrugia 1997)' _computing_publication_material 'SHELXL (Sheldrick 1997)' _refine_special_details ; Refinement on F^2^ for ALL reflections except for 0 with very negative F^2^ or flagged by the user for potential systematic errors. Weighted R-factors wR and all goodnesses of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The observed criterion of F^2^ > 2sigma(F^2^) is used only for calculating _R_factor_obs etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.1537P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary 'direct methods' _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geometrically _refine_ls_hydrogen_treatment mixed _refine_ls_extinction_method SHELXL _refine_ls_extinction_coef 0.0134(29) _refine_ls_extinction_expression 'Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^' _refine_ls_number_reflns 2592 _refine_ls_number_parameters 233 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.1233 _refine_ls_R_factor_gt 0.0743 _refine_ls_wR_factor_all 0.2662 _refine_ls_wR_factor_ref 0.1990 _refine_ls_goodness_of_fit_all 0.943 _refine_ls_goodness_of_fit_ref 1.052 _refine_ls_restrained_S_all 0.943 _refine_ls_restrained_S_ref 1.052 _refine_ls_shift/su_max 0.031 _refine_ls_shift/esd_mean 0.007 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_thermal_displace_type _atom_site_occupancy _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_group O1 O 0.1858(2) 0.4251(2) 0.47502(12) 0.0673(8) Uani 1 d . . C3 C 0.1277(2) 0.5639(3) 0.3618(2) 0.0517(8) Uani 1 d . . C4 C 0.0533(3) 0.5092(3) 0.3621(2) 0.0570(9) Uani 1 d . . H4A H 0.0052(25) 0.5319(38) 0.3210(21) 0.062(9) Uiso 1 d . . O11 O 0.1279(2) 0.5956(3) 0.23616(11) 0.0714(8) Uani 1 d . . C11 C 0.1425(2) 0.6571(3) 0.29744(15) 0.0527(8) Uani 1 d . . N12 N 0.1696(2) 0.7993(3) 0.30919(13) 0.0636(9) Uani 1 d . . O2 O 0.2705(2) 0.5577(3) 0.4232(2) 0.0846(9) Uani 1 d . . C9 C 0.0399(2) 0.4061(3) 0.4187(2) 0.0582(9) Uani 1 d . . C10 C 0.1085(2) 0.3680(3) 0.4747(2) 0.0591(10) Uani 1 d . . C2 C 0.1997(3) 0.5198(3) 0.4201(2) 0.0615(9) Uani 1 d . . C5 C -0.0360(3) 0.3394(4) 0.4201(2) 0.0718(11) Uani 1 d . . H5A H -0.0822(27) 0.3678(43) 0.3842(21) 0.068(11) Uiso 1 d . . C8 C 0.1019(4) 0.2661(5) 0.5308(3) 0.0794(14) Uani 1 d . . H8A H 0.1422(32) 0.2556(60) 0.5602(29) 0.100(20) Uiso 1 d . . C13 C 0.1837(4) 0.8808(4) 0.3802(2) 0.0710(13) Uani 1 d . . H13A H 0.2342(43) 0.8948(75) 0.3897(35) 0.139(25) Uiso 1 d . . H13B H 0.1646(21) 0.8157(35) 0.4097(18) 0.060(9) Uiso 1 d . . C17 C 0.1881(3) 0.8922(4) 0.2488(2) 0.0710(12) Uani 1 d . . H17A H 0.1733(23) 0.8316(39) 0.2055(20) 0.070(10) Uiso 1 d . . H17B H 0.2548(38) 0.9120(63) 0.2605(28) 0.122(17) Uiso 1 d . . C6 C -0.0423(4) 0.2372(4) 0.4748(3) 0.085(2) Uani 1 d . . H6A H -0.0845(31) 0.1950(50) 0.4784(24) 0.091(14) Uiso 1 d . . C7 C 0.0269(4) 0.2038(4) 0.5308(3) 0.0828(14) Uani 1 d . . H7A H 0.0168(30) 0.1270(53) 0.5656(24) 0.100(13) Uiso 1 d . . C14 C 0.1323(4) 1.0250(4) 0.3716(3) 0.087(2) Uani 1 d . . H14A H 0.1297(29) 1.0727(50) 0.4128(26) 0.100(13) Uiso 1 d . . H14B H 0.0692(35) 0.9894(46) 0.3553(25) 0.094(14) Uiso 1 d . . C16 C 0.1363(4) 1.0359(5) 0.2379(2) 0.090(2) Uani 1 d . . H16A H 0.0751(38) 1.0070(51) 0.2222(27) 0.104(17) Uiso 1 d . . H16B H 0.1457(27) 1.0921(45) 0.1955(24) 0.088(11) Uiso 1 d . . C15 C 0.1509(5) 1.1244(4) 0.3107(3) 0.109(2) Uani 1 d . . H15A H 0.2173(49) 1.1620(80) 0.3258(35) 0.158(26) Uiso 1 d . . H15B H 0.1051(39) 1.2167(64) 0.3002(32) 0.137(17) Uiso 1 d . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 O1 0.073(2) 0.0678(12) 0.0615(13) 0.0148(10) 0.0155(12) 0.0011(12) C3 0.066(2) 0.0430(13) 0.050(2) -0.0019(11) 0.021(2) 0.0018(14) C4 0.073(3) 0.0506(15) 0.051(2) -0.0015(13) 0.021(2) 0.004(2) O11 0.096(2) 0.0734(14) 0.0482(12) -0.0124(10) 0.0232(13) -0.0117(13) C11 0.065(2) 0.0529(14) 0.0443(14) -0.0014(12) 0.0203(15) 0.0047(14) N12 0.099(3) 0.0491(13) 0.0505(14) -0.0008(10) 0.034(2) -0.0012(14) O2 0.070(2) 0.098(2) 0.087(2) 0.0212(14) 0.019(2) -0.005(2) C9 0.078(3) 0.0464(14) 0.056(2) -0.0078(13) 0.029(2) -0.005(2) C10 0.081(3) 0.0449(13) 0.058(2) -0.0032(13) 0.030(2) -0.004(2) C2 0.070(3) 0.058(2) 0.062(2) 0.0053(14) 0.026(2) 0.000(2) C5 0.080(3) 0.072(2) 0.071(2) -0.007(2) 0.034(2) -0.009(2) C8 0.115(4) 0.062(2) 0.069(2) 0.010(2) 0.036(3) 0.002(2) C13 0.112(4) 0.053(2) 0.056(2) -0.0067(14) 0.035(2) -0.006(2) C17 0.101(3) 0.060(2) 0.064(2) 0.005(2) 0.046(2) -0.001(2) C6 0.108(4) 0.068(2) 0.098(3) -0.019(2) 0.062(3) -0.033(3) C7 0.119(4) 0.063(2) 0.081(3) 0.001(2) 0.053(3) -0.014(2) C14 0.126(5) 0.063(2) 0.085(3) -0.011(2) 0.055(3) 0.003(2) C16 0.129(5) 0.074(2) 0.081(3) 0.019(2) 0.051(3) 0.012(3) C15 0.175(7) 0.058(2) 0.115(4) 0.008(2) 0.079(4) 0.022(3) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag O1 C10 1.368(4) . ? O1 C2 1.370(4) . ? C3 C4 1.319(5) . ? C3 C2 1.461(5) . ? C3 C11 1.509(3) . ? C4 C9 1.435(4) . ? C4 H4A 0.99(4) . ? O11 C11 1.227(3) . ? C11 N12 1.321(4) . ? N12 C13 1.465(4) . ? N12 C17 1.468(3) . ? O2 C2 1.203(4) . ? C9 C5 1.388(5) . ? C9 C10 1.388(5) . ? C10 C8 1.390(5) . ? C5 C6 1.370(6) . ? C5 H5A 0.92(4) . ? C8 C7 1.353(8) . ? C8 H8A 0.76(5) . ? C13 C14 1.506(6) . ? C13 H13A 0.82(7) . ? C13 H13B 0.89(3) . ? C17 C16 1.506(6) . ? C17 H17A 0.95(4) . ? C17 H17B 1.09(6) . ? C6 C7 1.386(7) . ? C6 H6A 0.80(5) . ? C7 H7A 0.97(5) . ? C14 C15 1.510(6) . ? C14 H14A 0.88(5) . ? C14 H14B 1.06(5) . ? C16 C15 1.522(7) . ? C16 H16A 1.02(6) . ? C16 H16B 0.97(4) . ? C15 H15A 1.12(8) . ? C15 H15B 1.09(6) . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C10 O1 C2 122.2(3) . . ? C4 C3 C2 120.1(3) . . ? C4 C3 C11 121.3(3) . . ? C2 C3 C11 118.2(3) . . ? C3 C4 C9 122.0(4) . . ? C3 C4 H4A 120.6(19) . . ? C9 C4 H4A 117.2(20) . . ? O11 C11 N12 123.4(2) . . ? O11 C11 C3 117.4(3) . . ? N12 C11 C3 119.2(2) . . ? C11 N12 C13 125.6(2) . . ? C11 N12 C17 121.1(3) . . ? C13 N12 C17 113.3(3) . . ? C5 C9 C10 118.0(3) . . ? C5 C9 C4 124.7(4) . . ? C10 C9 C4 117.3(3) . . ? O1 C10 C9 121.0(3) . . ? O1 C10 C8 117.5(4) . . ? C9 C10 C8 121.4(4) . . ? O2 C2 O1 117.2(4) . . ? O2 C2 C3 125.4(3) . . ? O1 C2 C3 117.3(3) . . ? C6 C5 C9 120.7(5) . . ? C6 C5 H5A 121.1(24) . . ? C9 C5 H5A 118.2(24) . . ? C7 C8 C10 119.1(5) . . ? C7 C8 H8A 126.9(40) . . ? C10 C8 H8A 113.9(41) . . ? N12 C13 C14 110.0(4) . . ? N12 C13 H13A 102.0(44) . . ? C14 C13 H13A 114.8(47) . . ? N12 C13 H13B 103.4(19) . . ? C14 C13 H13B 109.0(20) . . ? H13A C13 H13B 116.6(51) . . ? N12 C17 C16 110.6(3) . . ? N12 C17 H17A 106.1(19) . . ? C16 C17 H17A 108.9(22) . . ? N12 C17 H17B 108.4(28) . . ? C16 C17 H17B 114.4(29) . . ? H17A C17 H17B 108.1(33) . . ? C5 C6 C7 119.9(5) . . ? C5 C6 H6A 125.0(34) . . ? C7 C6 H6A 115.0(33) . . ? C8 C7 C6 120.8(4) . . ? C8 C7 H7A 125.1(29) . . ? C6 C7 H7A 113.8(29) . . ? C13 C14 C15 110.6(4) . . ? C13 C14 H14A 116.4(30) . . ? C15 C14 H14A 115.7(28) . . ? C13 C14 H14B 106.2(23) . . ? C15 C14 H14B 108.1(24) . . ? H14A C14 H14B 98.3(37) . . ? C17 C16 C15 109.6(5) . . ? C17 C16 H16A 109.2(26) . . ? C15 C16 H16A 108.8(26) . . ? C17 C16 H16B 109.8(23) . . ? C15 C16 H16B 115.9(23) . . ? H16A C16 H16B 103.3(39) . . ? C14 C15 C16 110.5(4) . . ? C14 C15 H15A 109.7(35) . . ? C16 C15 H15A 108.5(33) . . ? C14 C15 H15B 107.8(29) . . ? C16 C15 H15B 104.8(32) . . ? H15A C15 H15B 115.3(49) . . ? _refine_diff_density_max 0.385 _refine_diff_density_min -0.403 _refine_diff_density_rms 0.092 data_05 # 1. SUBMISSION DETAILS _publ_contact_author ; Itzia I. Padilla-Mart/'inez Departamento de Qu/'imica UPIBI-IPN Av. Acueducto s/n, Col. Barrio la Laguna Ticoman C.P 07340 M/'exico, D. F. ; _publ_contact_author_phone '525 729 6000 EXT 56324' _publ_contact_author_fax '525 729 6000 EXT 56325' _publ_contact_author_email ipadilla@acei.upibi.ipn.mx _publ_requested_journal 'Crystal Growth and Design' _publ_requested_category 'LC' # 3. TITLE AND AUTHOR LIST _publ_section_title ; Acetoamidocoumarin ; _publ_section_abstract ; The crystallographic study of 3-carboxycoumarins 1-4 and 3-amidocoumarin 5-6 is reported in the context of crystal engineering. The formers can be depicted as two fused rings with opposed polarity which appeared associated through paralled displaced pi-stacking interactions. The benzenoid ring B and the lactone ring L of one molecule interact with the ing L' and benzenoid ring B' of the partner molecule with mean interplanar and mean intercentroid distances ranging between 3.385(6)-3.67(2)A and 3.679(1)-4.081(3)A, respectively. Among the six possible arrangements formed by pairwise overlapping the anti tail-to-tail orientation was the most frequently observed. Pairing through pi-stacking interactions is less favoured when changing the 3-carboxy for a 3-amido group or even annulled increasing the H-bonding capability of the 3-amido group as in 3-oxalamate 6. These fused polar rings can also associate through pi-stacking interactions in the presence of weak interactions such C--H..X(X=O or aromatic ring), as long as these associations do not slip so far the molecular planes to avoid subsequent pi-stacking interactions ; _publ_section_comment ; The supramolecular structure observed in 3-carboxy and 3-amidocoumarins 1-6 is directed by a balance between parallel displaced pi-stacking, weak aryl C-X..pi and strong N-H..O hydrogen bonding interactions. ; loop_ _publ_author_name _publ_author_address ; 'Efr/'en V. Garc/'ia-B/'aez' Departamento de Qu/'imica UPIBI-IPN Av. Acueducto s/n Col. Barrio la Laguna Ticoman C.P. 07340. M/'exico, D. F. ; 'Francisco J. Mart/'inez-Mart/'inez' Departamento de Qu/'imica UPIBI-IPN Av. Acueducto s/n, Col. Barrio la Laguna Ticoman C.P. 07340. M/'exico D. F. ; 'Herbert Hopfl' Centro de Investigaciones Qu/'imicas Universidad Autonoma del Estado de Morelos Cuernavaca Morelos ; _audit_creation_method SHELXL-97 _chemical_name_systematic ; Acetoamidocoumarin ; _chemical_name_common ? _chemical_formula_moiety ? _chemical_formula_structural ? _chemical_formula_analytical 'C11 H9 N O3' _chemical_formula_sum 'C11 H9 N O3' _chemical_formula_weight 203.19 _chemical_melting_point ? _chemical_compound_source ? loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source 'C' 'C' 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 'H' 'H' 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 'N' 'N' 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 'O' 'O' 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Monoclinic _symmetry_space_group_name_H-M P2(1)/c loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y-1/2, z-1/2' _cell_length_a 10.0907(13) _cell_length_b 4.8785(6) _cell_length_c 19.096(2) _cell_angle_alpha 90.00 _cell_angle_beta 99.591(2) _cell_angle_gamma 90.00 _cell_volume 926.9(2) _cell_formula_units_Z 4 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used 200 _cell_measurement_theta_min 20 _cell_measurement_theta_max 25 _exptl_crystal_description rectangular _exptl_crystal_colour colorless _exptl_crystal_size_max 0.5 _exptl_crystal_size_mid 0.4 _exptl_crystal_size_min 0.4 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.456 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 424 _exptl_absorpt_coefficient_mu 0.108 _exptl_absorpt_correction_type none _exptl_absorpt_correction_T_min ? _exptl_absorpt_correction_T_max ? _exptl_absorpt_process_details ? _exptl_special_details ; Diffractometer operator H. Hopfl scanspeed_seconds/frame 10 1200 frames measured in phi (0-360) with chi=0 and om=2th=25 65 frames measured in om (15-35) with chi=280, 2th=29 and phi=0 Crystal mounted in glass fibber ; _diffrn_ambient_temperature 293(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Bruker SMART Area-detector' _diffrn_measurement_method 'phi and omega scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time 0 _diffrn_standards_decay_% ? _diffrn_reflns_number 10109 _diffrn_reflns_av_R_equivalents 0.0454 _diffrn_reflns_av_sigmaI/netI 0.0474 _diffrn_reflns_limit_h_min -12 _diffrn_reflns_limit_h_max 13 _diffrn_reflns_limit_k_min -6 _diffrn_reflns_limit_k_max 6 _diffrn_reflns_limit_l_min -24 _diffrn_reflns_limit_l_max 24 _diffrn_reflns_theta_min 2.05 _diffrn_reflns_theta_max 27.58 _reflns_number_total 2145 _reflns_number_gt 1373 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'SMART (V4.C50)' _computing_cell_refinement 'SMART (V4.C50)' _computing_data_reduction 'SAINT (V4.D50)' _computing_structure_solution 'SHELXS (Sheldrick 1997)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'XP (SHELXTL-Ver.5)' _computing_publication_material 'SHELXL (Sheldrick 1997)' _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0616P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment mixed _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 2145 _refine_ls_number_parameters 172 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.1020 _refine_ls_R_factor_gt 0.0590 _refine_ls_wR_factor_ref 0.1350 _refine_ls_wR_factor_gt 0.1188 _refine_ls_goodness_of_fit_ref 1.031 _refine_ls_restrained_S_all 1.031 _refine_ls_shift/su_max 0.002 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group O1 O 0.15948(14) 0.5326(3) 0.12189(7) 0.0450(4) Uani 1 1 d . . . O2 O 0.03880(16) 0.2148(3) 0.05966(8) 0.0562(5) Uani 1 1 d . . . C9 C 0.2641(2) 0.7184(4) 0.13104(10) 0.0388(5) Uani 1 1 d . . . C4 C 0.3148(2) 0.5870(5) 0.01622(12) 0.0434(5) Uani 1 1 d . . . H4A H 0.369(2) 0.607(5) -0.0191(11) 0.051(6) Uiso 1 1 d . . . N11 N 0.16771(19) 0.2507(4) -0.05262(10) 0.0446(5) Uani 1 1 d . . . H11A H 0.104(2) 0.134(5) -0.0474(11) 0.053(7) Uiso 1 1 d . . . C5 C 0.4513(2) 0.9336(5) 0.09417(13) 0.0489(6) Uani 1 1 d . . . H5A H 0.507(2) 0.948(4) 0.0604(11) 0.043(6) Uiso 1 1 d . . . C10 C 0.3455(2) 0.7451(4) 0.08005(11) 0.0394(5) Uani 1 1 d . . . C8 C 0.2828(2) 0.8705(5) 0.19289(12) 0.0461(6) Uani 1 1 d . . . H8A H 0.223(2) 0.842(4) 0.2256(10) 0.041(6) Uiso 1 1 d . . . C3 C 0.21154(19) 0.4117(4) 0.00720(11) 0.0385(5) Uani 1 1 d . . . C2 C 0.1305(2) 0.3753(4) 0.06277(11) 0.0396(5) Uani 1 1 d . . . O12 O 0.26655(17) 0.4809(4) -0.13217(8) 0.0664(6) Uani 1 1 d . . . C6 C 0.4709(3) 1.0877(5) 0.15503(13) 0.0514(6) Uani 1 1 d . . . H6A H 0.542(2) 1.210(4) 0.1640(10) 0.042(6) Uiso 1 1 d . . . C7 C 0.3858(2) 1.0570(5) 0.20375(13) 0.0498(6) Uani 1 1 d . . . H7A H 0.397(2) 1.150(5) 0.2476(12) 0.059(7) Uiso 1 1 d . . . C12 C 0.1922(2) 0.3003(4) -0.11950(11) 0.0451(6) Uani 1 1 d . . . C13 C 0.1197(4) 0.1146(7) -0.17541(16) 0.0617(8) Uani 1 1 d . . . H13A H 0.149(3) 0.130(7) -0.2150(19) 0.115(12) Uiso 1 1 d . . . H13B H 0.136(4) -0.073(11) -0.162(2) 0.19(2) Uiso 1 1 d . . . H13C H 0.037(5) 0.143(10) -0.181(2) 0.18(2) Uiso 1 1 d . . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 O1 0.0490(9) 0.0466(9) 0.0405(9) -0.0022(7) 0.0106(7) -0.0109(7) O2 0.0605(10) 0.0562(10) 0.0539(10) -0.0056(8) 0.0159(8) -0.0230(8) C9 0.0397(12) 0.0341(12) 0.0407(12) 0.0037(9) 0.0009(9) -0.0005(9) C4 0.0452(13) 0.0479(13) 0.0384(13) 0.0034(10) 0.0109(10) -0.0028(11) N11 0.0531(12) 0.0409(11) 0.0405(11) -0.0012(9) 0.0096(9) -0.0108(9) C5 0.0494(14) 0.0549(15) 0.0417(14) 0.0064(11) 0.0058(11) -0.0129(12) C10 0.0428(12) 0.0386(12) 0.0353(11) 0.0077(9) 0.0018(9) -0.0014(10) C8 0.0496(14) 0.0477(14) 0.0406(13) 0.0013(11) 0.0066(11) -0.0010(11) C3 0.0420(12) 0.0340(11) 0.0392(12) 0.0020(9) 0.0055(9) -0.0014(10) C2 0.0411(12) 0.0355(12) 0.0410(13) 0.0026(10) 0.0037(10) -0.0039(10) O12 0.0814(12) 0.0707(12) 0.0510(11) -0.0011(8) 0.0227(9) -0.0297(10) C6 0.0559(15) 0.0466(14) 0.0466(14) 0.0060(11) -0.0064(12) -0.0145(12) C7 0.0598(15) 0.0446(13) 0.0415(14) -0.0031(11) -0.0020(12) -0.0021(12) C12 0.0495(13) 0.0450(13) 0.0426(13) 0.0004(11) 0.0128(10) 0.0000(11) C13 0.076(2) 0.068(2) 0.0430(16) -0.0131(13) 0.0147(14) -0.0133(16) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag O1 C2 1.356(2) . ? O1 C9 1.380(2) . ? O2 C2 1.206(2) . ? C9 C8 1.381(3) . ? C9 C10 1.381(3) . ? C4 C3 1.337(3) . ? C4 C10 1.432(3) . ? C4 H4A 0.94(2) . ? N11 C12 1.362(3) . ? N11 C3 1.396(3) . ? N11 H11A 0.88(2) . ? C5 C6 1.370(3) . ? C5 C10 1.401(3) . ? C5 H5A 0.92(2) . ? C8 C7 1.371(3) . ? C8 H8A 0.95(2) . ? C3 C2 1.455(3) . ? O12 C12 1.208(2) . ? C6 C7 1.375(3) . ? C6 H6A 0.93(2) . ? C7 H7A 0.94(2) . ? C12 C13 1.495(3) . ? C13 H13A 0.86(4) . ? C13 H13B 0.96(5) . ? C13 H13C 0.83(4) . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C2 O1 C9 122.10(16) . . ? O1 C9 C8 117.00(19) . . ? O1 C9 C10 120.34(18) . . ? C8 C9 C10 122.7(2) . . ? C3 C4 C10 120.5(2) . . ? C3 C4 H4A 120.4(13) . . ? C10 C4 H4A 119.1(13) . . ? C12 N11 C3 125.79(19) . . ? C12 N11 H11A 118.2(14) . . ? C3 N11 H11A 114.2(15) . . ? C6 C5 C10 121.4(2) . . ? C6 C5 H5A 122.0(13) . . ? C10 C5 H5A 116.6(13) . . ? C9 C10 C5 116.8(2) . . ? C9 C10 C4 118.66(19) . . ? C5 C10 C4 124.5(2) . . ? C7 C8 C9 118.6(2) . . ? C7 C8 H8A 123.3(12) . . ? C9 C8 H8A 118.2(12) . . ? C4 C3 N11 126.8(2) . . ? C4 C3 C2 120.3(2) . . ? N11 C3 C2 112.85(18) . . ? O2 C2 O1 117.76(19) . . ? O2 C2 C3 124.3(2) . . ? O1 C2 C3 117.96(18) . . ? C5 C6 C7 119.8(2) . . ? C5 C6 H6A 120.5(13) . . ? C7 C6 H6A 119.7(12) . . ? C8 C7 C6 120.9(2) . . ? C8 C7 H7A 115.6(14) . . ? C6 C7 H7A 123.3(14) . . ? O12 C12 N11 122.2(2) . . ? O12 C12 C13 123.0(2) . . ? N11 C12 C13 114.7(2) . . ? C12 C13 H13A 112(2) . . ? C12 C13 H13B 110(3) . . ? H13A C13 H13B 105(3) . . ? C12 C13 H13C 110(3) . . ? H13A C13 H13C 111(4) . . ? H13B C13 H13C 108(4) . . ? _diffrn_measured_fraction_theta_max 0.994 _diffrn_reflns_theta_full 27.58 _diffrn_measured_fraction_theta_full 0.994 _refine_diff_density_max 0.246 _refine_diff_density_min -0.232 _refine_diff_density_rms 0.039 data_06 # 1. SUBMISSION DETAILS _publ_contact_author ; Itzia I. Padilla-Mart/'inez Departamento de Qu/'imica UPIBI-IPN Av. Acueducto s/n, Col. Barrio la Laguna Ticoman C.P 07340 M/'exico, D. F. ; _publ_contact_author_phone '525 729 6000 EXT 56324' _publ_contact_author_fax '525 729 6000 EXT 56325' _publ_contact_author_email ipadilla@acei.upibi.ipn.mx _publ_requested_journal 'Crystal Growth and Design' _publ_requested_category 'LC' # 3. TITLE AND AUTHOR LIST _publ_section_title ; Ethyl N-[(2H-1-benzopyran-2-oxo-3-yl)amin]oxalamate ; _publ_section_abstract ; The crystallographic study of 3-carboxycoumarins 1-4 and 3-amidocoumarin 5-6 is reported in the context of crystal engineering. The formers can be depicted as two fused rings with opposed polarity which appeared associated through paralled displaced pi-stacking interactions. The benzenoid ring B and the lactone ring L of one molecule interact with the ing L' and benzenoid ring B' of the partner molecule with mean interplanar and mean intercentroid distances ranging between 3.385(6)-3.67(2)A and 3.679(1)-4.081(3)A, respectively. Among the six possible arrangements formed by pairwise overlapping the anti tail-to-tail orientation was the most frequently observed. Pairing through pi-stacking interactions is less favoured when changing the 3-carboxy for a 3-amido group or even annulled increasing the H-bonding capability of the 3-amido group as in 3-oxalamate 6. These fused polar rings can also associate through pi-stacking interactions in the presence of weak interactions such C--H..X(X=O or aromatic ring), as long as these associations do not slip so far the molecular planes to avoid subsequent pi-stacking interactions ; _publ_section_comment ; The supramolecular structure observed in 3-carboxy and 3-amidocoumarins 1-6 is directed by a balance between parallel displaced pi-stacking, weak aryl C-X..pi and strong N-H..O hydrogen bonding interactions. ; loop_ _publ_author_name _publ_author_address ; 'Efr/'en V. Garc/'ia-B/'aez' Departamento de Qu/'imica UPIBI-IPN Av. Acueducto s/n Col. Barrio la Laguna Ticoman C.P. 07340. M/'exico, D. F. ; 'Francisco J. Mart/'inez-Mart/'inez' Departamento de Qu/'imica UPIBI-IPN Av. Acueducto s/n, Col. Barrio la Laguna Ticoman C.P. 07340. M/'exico D. F. ; 'Herbert Hopfl' Centro de Investigaciones Qu/'imicas Universidad Autonoma del Estado de Morelos Cuernavaca Morelos ; ? ; _chemical_name_common ? _chemical_formula_moiety ? _chemical_formula_structural ? ; _chemical_formula_moiety 'C13 H11 N O5' _chemical_formula_sum 'C13 H11 N O5' _chemical_formula_weight 261.23 _chemical_formula_analytical ? _chemical_melting_point ? _chemical_compound_source ? loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source 'C' 'C' 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 'H' 'H' 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 'N' 'N' 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 'O' 'O' 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Monoclinic _symmetry_space_group_name_H-M P2(1)/n loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, y+1/2, -z+1/2' '-x, -y, -z' 'x-1/2, -y-1/2, z-1/2' _cell_length_a 5.7160(10) _cell_length_b 18.239(4) _cell_length_c 11.637(2) _cell_angle_alpha 90.00 _cell_angle_beta 99.85(3) _cell_angle_gamma 90.00 _cell_volume 1195.3(4) _cell_formula_units_Z 4 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used 25 _cell_measurement_theta_min 2.15 _cell_measurement_theta_max 27 _exptl_crystal_description prism _exptl_crystal_colour colorless _exptl_crystal_size_max 0.4 _exptl_crystal_size_mid 0.3 _exptl_crystal_size_min 0.2 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.452 _exptl_crystal_density_method ? _exptl_crystal_F_000 544 _exptl_absorpt_coefficient_mu 0.113 _exptl_absorpt_correction_type none _exptl_absorpt_correction_T_min ? _exptl_absorpt_correction_T_max ? _exptl_special_details ; Diffractometer operator Efren Garcia scanwidth_degrees 0.7 low_scanspeed_degrees/min 16.1 high_scanspeed_degrees/min 60 Background measurement : Stationary crystal and stationary counter at the beginning and end of scan, each for 25% of total scan time Crystal mounted in glass fibber ; _diffrn_ambient_temperature 293(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device 'Enraf-Nonius CAD4' _diffrn_measurement_method \w _diffrn_standards_number 3 _diffrn_standards_interval_count 100 _diffrn_standards_interval_time ? _diffrn_standards_decay_% 0 _diffrn_reflns_number 7276 _diffrn_reflns_av_R_equivalents 0.0330 _diffrn_reflns_av_sigmaI/netI 0.0266 _diffrn_reflns_limit_h_min -6 _diffrn_reflns_limit_h_max 6 _diffrn_reflns_limit_k_min -21 _diffrn_reflns_limit_k_max 19 _diffrn_reflns_limit_l_min -13 _diffrn_reflns_limit_l_max 13 _diffrn_reflns_theta_min 2.10 _diffrn_reflns_theta_max 25.03 _diffrn_reflns_theta_full 25.03 _diffrn_measured_fraction_theta_full 0.972 _diffrn_measured_fraction_theta_max 0.972 _reflns_number_total 2114 _reflns_number_gt 1629 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'CAD4-EXPRESS (Ver. 2.00)' _computing_cell_refinement 'CAD4-EXPRESS (Ver. 2.00)' _computing_data_reduction 'XSCANS (Ver. 2.0)' _computing_structure_solution 'SHELXS-86 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-93 (Sheldrick, 1993)' _computing_molecular_graphics 'Cameron-WinGx (Farrugia 1997)' _computing_publication_material 'SHELXL (Sheldrick 1997)'' _refine_special_details ; Refinement on F^2^ for ALL reflections except for 0 with very negative F^2^ or flagged by the user for potential systematic errors. Weighted R-factors wR and all goodnesses of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The observed criterion of F^2^ > 2sigma(F^2^) is used only for calculating _R_factor_obs etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0638P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary 'direct methods' _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geometrically _refine_ls_hydrogen_treatment mixed _refine_ls_extinction_method SHELXL _refine_ls_extinction_coef 0.0695(50) _refine_ls_extinction_expression 'Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^' _refine_ls_number_reflns 2114 _refine_ls_number_parameters 217 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0490 _refine_ls_R_factor_gt 0.0371 _refine_ls_wR_factor_all 0.1007 _refine_ls_wR_factor_ref 0.0938 _refine_ls_goodness_of_fit_all 1.031 _refine_ls_goodness_of_fit_ref 1.111 _refine_ls_restrained_S_all 1.031 _refine_ls_restrained_S_ref 1.111 _refine_ls_shift/su_max 0.001 _refine_ls_shift/esd_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_thermal_displace_type _atom_site_occupancy _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_group O1 O -0.8083(2) 0.83511(6) 0.39515(9) 0.0508(3) Uani 1 d . . O2 O -0.6569(2) 0.76687(6) 0.54566(10) 0.0604(3) Uani 1 d . . O12 O 0.0553(2) 0.92054(6) 0.59704(9) 0.0513(3) Uani 1 d . . O13 O -0.0061(2) 0.77207(8) 0.77716(11) 0.0778(4) Uani 1 d . . O14 O 0.2875(2) 0.85424(6) 0.78931(9) 0.0555(3) Uani 1 d . . N11 N -0.2510(2) 0.84014(8) 0.59397(11) 0.0475(3) Uani 1 d . . H11A H -0.2935(32) 0.8056(10) 0.6313(16) 0.061(5) Uiso 1 d . . C2 C -0.6303(3) 0.81848(9) 0.48361(13) 0.0462(4) Uani 1 d . . C3 C -0.4179(2) 0.86436(8) 0.50010(12) 0.0419(4) Uani 1 d . . C4 C -0.4012(3) 0.92262(8) 0.43116(12) 0.0447(4) Uani 1 d . . H4A H -0.2620(29) 0.9535(9) 0.4433(13) 0.050(4) Uiso 1 d . . C5 C -0.5951(3) 0.99886(9) 0.26333(13) 0.0515(4) Uani 1 d . . H5A H -0.4619(32) 1.0292(10) 0.2748(14) 0.064(5) Uiso 1 d . . C6 C -0.7895(3) 1.01206(10) 0.17786(15) 0.0591(5) Uani 1 d . . H6A H -0.7835(30) 1.0539(10) 0.1249(15) 0.067(5) Uiso 1 d . . C7 C -0.9850(3) 0.96655(11) 0.16484(15) 0.0627(5) Uani 1 d . . H7A H -1.1272(34) 0.9752(10) 0.1040(16) 0.072(5) Uiso 1 d . . C8 C -0.9899(3) 0.90684(11) 0.23692(14) 0.0568(4) Uani 1 d . . H8A H -1.1209(35) 0.8740(9) 0.2299(14) 0.058(5) Uiso 1 d . . C9 C -0.7952(3) 0.89455(8) 0.32297(12) 0.0451(4) Uani 1 d . . C10 C -0.5955(3) 0.93909(8) 0.33882(12) 0.0436(4) Uani 1 d . . C12 C -0.0357(3) 0.86846(8) 0.63591(12) 0.0426(4) Uani 1 d . . C13 C 0.0831(3) 0.82510(9) 0.74293(13) 0.0480(4) Uani 1 d . . C15 C 0.4196(4) 0.81852(11) 0.8936(2) 0.0614(5) Uani 1 d . . H15A H 0.5984(38) 0.8259(10) 0.8844(16) 0.081(6) Uiso 1 d . . H15B H 0.3685(32) 0.7656(11) 0.8931(15) 0.069(5) Uiso 1 d . . C16 C 0.3711(6) 0.8556(2) 0.9993(2) 0.0853(7) Uani 1 d . . H16A H 0.4663(43) 0.8346(13) 1.0667(21) 0.097(7) Uiso 1 d . . H16B H 0.4144(40) 0.9061(14) 0.9925(18) 0.094(8) Uiso 1 d . . H16C H 0.2016(49) 0.8493(13) 1.0035(20) 0.112(9) Uiso 1 d . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 O1 0.0416(6) 0.0570(7) 0.0526(6) -0.0027(5) 0.0049(5) -0.0100(5) O2 0.0582(7) 0.0596(7) 0.0624(7) 0.0072(6) 0.0076(5) -0.0170(5) O12 0.0473(6) 0.0535(7) 0.0525(6) 0.0061(5) 0.0064(5) -0.0081(5) O13 0.0717(8) 0.0849(10) 0.0721(8) 0.0308(7) -0.0015(6) -0.0241(7) O14 0.0496(6) 0.0534(7) 0.0583(7) 0.0070(5) -0.0050(5) -0.0009(5) N11 0.0450(8) 0.0500(8) 0.0470(7) 0.0033(6) 0.0062(6) -0.0076(6) C2 0.0438(9) 0.0492(9) 0.0465(8) -0.0064(7) 0.0106(7) -0.0061(7) C3 0.0395(8) 0.0460(8) 0.0411(8) -0.0057(6) 0.0100(6) -0.0035(6) C4 0.0415(8) 0.0480(9) 0.0458(8) -0.0058(6) 0.0106(7) -0.0051(7) C5 0.0533(10) 0.0515(10) 0.0507(9) -0.0014(7) 0.0118(8) -0.0014(8) C6 0.0657(11) 0.0615(11) 0.0500(9) 0.0021(8) 0.0097(8) 0.0065(9) C7 0.0567(11) 0.0789(13) 0.0490(9) -0.0043(8) -0.0005(8) 0.0104(9) C8 0.0451(10) 0.0711(12) 0.0531(9) -0.0097(8) 0.0048(8) -0.0026(8) C9 0.0435(8) 0.0505(9) 0.0427(8) -0.0066(7) 0.0111(7) -0.0011(7) C10 0.0421(8) 0.0475(8) 0.0427(8) -0.0074(6) 0.0118(6) -0.0005(6) C12 0.0414(8) 0.0454(9) 0.0425(8) -0.0030(6) 0.0113(6) -0.0022(7) C13 0.0474(9) 0.0522(9) 0.0455(8) 0.0010(7) 0.0109(7) -0.0035(7) C15 0.0581(11) 0.0581(11) 0.0625(11) 0.0066(8) -0.0050(9) 0.0105(9) C16 0.102(2) 0.090(2) 0.0595(13) 0.0015(11) 0.0016(13) 0.023(2) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag O1 C2 1.353(2) . ? O1 C9 1.381(2) . ? O2 C2 1.212(2) . ? O12 C12 1.207(2) . ? O13 C13 1.193(2) . ? O14 C13 1.312(2) . ? O14 C15 1.467(2) . ? N11 C12 1.347(2) . ? N11 C3 1.394(2) . ? N11 H11A 0.83(2) . ? C2 C3 1.459(2) . ? C3 C4 1.345(2) . ? C4 C10 1.439(2) . ? C4 H4A 0.96(2) . ? C5 C6 1.380(2) . ? C5 C10 1.400(2) . ? C5 H5A 0.93(2) . ? C6 C7 1.379(3) . ? C6 H6A 0.99(2) . ? C7 C8 1.378(3) . ? C7 H7A 0.99(2) . ? C8 C9 1.382(2) . ? C8 H8A 0.95(2) . ? C9 C10 1.387(2) . ? C12 C13 1.532(2) . ? C15 C16 1.471(3) . ? C15 H15A 1.05(2) . ? C15 H15B 1.01(2) . ? C16 H16A 0.96(3) . ? C16 H16B 0.96(2) . ? C16 H16C 0.98(3) . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C2 O1 C9 121.78(11) . . ? C13 O14 C15 117.16(14) . . ? C12 N11 C3 128.56(14) . . ? C12 N11 H11A 115.8(13) . . ? C3 N11 H11A 115.5(13) . . ? O2 C2 O1 118.22(13) . . ? O2 C2 C3 123.61(14) . . ? O1 C2 C3 118.17(13) . . ? C4 C3 N11 127.50(14) . . ? C4 C3 C2 121.14(14) . . ? N11 C3 C2 111.34(13) . . ? C3 C4 C10 119.06(14) . . ? C3 C4 H4A 121.0(9) . . ? C10 C4 H4A 120.0(9) . . ? C6 C5 C10 120.0(2) . . ? C6 C5 H5A 122.5(11) . . ? C10 C5 H5A 117.5(11) . . ? C7 C6 C5 120.8(2) . . ? C7 C6 H6A 120.8(10) . . ? C5 C6 H6A 118.4(11) . . ? C8 C7 C6 120.6(2) . . ? C8 C7 H7A 117.3(10) . . ? C6 C7 H7A 122.1(10) . . ? C7 C8 C9 118.1(2) . . ? C7 C8 H8A 122.9(11) . . ? C9 C8 H8A 119.0(11) . . ? O1 C9 C8 116.55(14) . . ? O1 C9 C10 120.52(13) . . ? C8 C9 C10 122.93(15) . . ? C9 C10 C5 117.52(15) . . ? C9 C10 C4 119.31(14) . . ? C5 C10 C4 123.17(15) . . ? O12 C12 N11 126.24(14) . . ? O12 C12 C13 123.45(13) . . ? N11 C12 C13 110.31(13) . . ? O13 C13 O14 126.30(15) . . ? O13 C13 C12 122.30(14) . . ? O14 C13 C12 111.39(13) . . ? O14 C15 C16 110.1(2) . . ? O14 C15 H15A 103.3(10) . . ? C16 C15 H15A 110.5(11) . . ? O14 C15 H15B 108.2(10) . . ? C16 C15 H15B 110.4(10) . . ? H15A C15 H15B 114.0(15) . . ? C15 C16 H16A 109.9(14) . . ? C15 C16 H16B 106.5(13) . . ? H16A C16 H16B 109.5(20) . . ? C15 C16 H16C 108.4(15) . . ? H16A C16 H16C 109.8(20) . . ? H16B C16 H16C 112.6(21) . . ? _refine_diff_density_max 0.142 _refine_diff_density_min -0.210 _refine_diff_density_rms 0.049