#============================================================================== # 1. SUBMISSION DETAILS _publ_contact_author ; Peter G. Jones Institut f\"ur Anorganische und Analytische Chemie Technische Universit\"at Braunschweig Postfach 3329 38023 Braunschweig Germany ; _publ_contact_author_phone '049 531 391-5382' _publ_contact_author_fax '049 531 391-5387' _publ_contact_author_email p.jones@tu-bs.de _publ_requested_journal 'J. Org. Chem.' #============================================================================== # 3. TITLE AND AUTHOR LIST _publ_section_title ; Synthesis of 5- and 6-Unsubstituted Pyrrolidines and Piperidines from Donor-Acceptor Cyclopropanes and Cyclobutanes: 1,3,5 Triazinanes as Surrogate for Formylimines ; loop_ _publ_author_name _publ_author_address 'Garve, Lennart' ; Institut f\"ur Organische Chemie Technische Universit\"at Braunschweig Postfach 3329 38023 Braunschweig Germany ; 'Kreft, Alexander' ; Institut f\"ur Organische Chemie Technische Universit\"at Braunschweig Postfach 3329 38023 Braunschweig Germany ; 'Jones, Peter G.' ; Institut f\"ur Anorganische und Analytische Chemie Technische Universit\"at Braunschweig Postfach 3329 38023 Braunschweig Germany ; 'Werz, Daniel' ; Institut f\"ur Organische Chemie Technische Universit\"at Braunschweig Postfach 3329 38023 Braunschweig Germany ; #============================================================================= # cif data for "varge" #============================================================================= data_varge _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C20 H20 Br N O4' _chemical_formula_weight 418.28 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source 'C' 'C' 0.0181 0.0091 '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' 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 'O' 'O' 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 'Br' 'Br' -0.6763 1.2805 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M 'P 21/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 13.3569(2) _cell_length_b 8.15707(12) _cell_length_c 17.6178(3) _cell_angle_alpha 90.00 _cell_angle_beta 107.1564(9) _cell_angle_gamma 90.00 _cell_volume 1834.10(5) _cell_formula_units_Z 4 _cell_measurement_temperature 100(2) _cell_measurement_reflns_used 25264 _cell_measurement_theta_min 3.4460 _cell_measurement_theta_max 75.9600 _exptl_crystal_description plate _exptl_crystal_colour colourless _exptl_crystal_size_max 0.20 _exptl_crystal_size_mid 0.10 _exptl_crystal_size_min 0.04 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.515 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 856 _exptl_absorpt_coefficient_mu 3.271 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.63491 _exptl_absorpt_correction_T_max 1.00000 _exptl_absorpt_process_details ; CrysAlisPro 1.171.38.43c (Rigaku Oxford Diffraction, 2015) Empirical absorption correction using spherical harmonics, implemented in SCALE3 ABSPACK scaling algorithm. ; _exptl_special_details ; ? ; _diffrn_ambient_temperature 100(2) _diffrn_radiation_wavelength 1.54184 _diffrn_radiation_type CuK\a _diffrn_source 'micro-focus sealed X-ray tube' _diffrn_radiation_monochromator mirror _diffrn_measurement_device_type 'Oxford Diffraction Xcalibur, Atlas, Nova' _diffrn_measurement_method \w-scan _diffrn_detector_area_resol_mean 10.3543 _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 54952 _diffrn_reflns_av_R_equivalents 0.0589 _diffrn_reflns_av_sigmaI/netI 0.0194 _diffrn_reflns_limit_h_min -16 _diffrn_reflns_limit_h_max 16 _diffrn_reflns_limit_k_min -10 _diffrn_reflns_limit_k_max 10 _diffrn_reflns_limit_l_min -22 _diffrn_reflns_limit_l_max 21 _diffrn_reflns_theta_min 3.46 _diffrn_reflns_theta_max 76.20 _reflns_number_total 3838 _reflns_number_gt 3445 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'CrysAlisPro 1.171.38.43c (Rigaku OD, 2015)' _computing_cell_refinement 'CrysAlisPro 1.171.38.43c (Rigaku OD, 2015)' _computing_data_reduction 'CrysAlisPro 1.171.38.43c (Rigaku OD, 2015)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Siemens XP' _computing_publication_material SHELXL-97 _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^)+(0.0389P)^2^+1.3205P] 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 constr _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 3838 _refine_ls_number_parameters 237 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0333 _refine_ls_R_factor_gt 0.0286 _refine_ls_wR_factor_ref 0.0746 _refine_ls_wR_factor_gt 0.0709 _refine_ls_goodness_of_fit_ref 1.046 _refine_ls_restrained_S_all 1.046 _refine_ls_shift/su_max 0.001 _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 N1 N 0.73701(12) 0.3912(2) 0.42202(9) 0.0235(3) Uani 1 1 d . . . C2 C 0.83357(14) 0.4830(2) 0.45161(11) 0.0235(4) Uani 1 1 d . . . H2A H 0.8943 0.4082 0.4701 0.028 Uiso 1 1 calc R . . H2B H 0.8309 0.5553 0.4961 0.028 Uiso 1 1 calc R . . C3 C 0.84108(14) 0.5848(2) 0.37959(11) 0.0208(4) Uani 1 1 d . . . C4 C 0.72560(14) 0.6050(2) 0.33045(11) 0.0226(4) Uani 1 1 d . . . H4A H 0.7195 0.6186 0.2734 0.027 Uiso 1 1 calc R . . H4B H 0.6943 0.7018 0.3486 0.027 Uiso 1 1 calc R . . C5 C 0.67047(13) 0.4463(2) 0.34410(10) 0.0199(3) Uani 1 1 d . . . H5 H 0.6713 0.3634 0.3025 0.024 Uiso 1 1 calc R . . C6 C 0.71884(14) 0.2532(2) 0.46084(11) 0.0197(3) Uani 1 1 d . . . C7 C 0.78551(14) 0.2138(2) 0.53698(11) 0.0213(4) Uani 1 1 d . . . H7 H 0.8437 0.2825 0.5610 0.026 Uiso 1 1 calc R . . C8 C 0.76730(14) 0.0762(2) 0.57717(11) 0.0233(4) Uani 1 1 d . . . H8 H 0.8127 0.0511 0.6285 0.028 Uiso 1 1 calc R . . C9 C 0.68300(14) -0.0245(2) 0.54245(11) 0.0219(4) Uani 1 1 d . . . C10 C 0.61625(15) 0.0108(2) 0.46747(11) 0.0221(4) Uani 1 1 d . . . H10 H 0.5589 -0.0597 0.4438 0.026 Uiso 1 1 calc R . . C11 C 0.63343(14) 0.1489(2) 0.42714(11) 0.0206(3) Uani 1 1 d . . . H11 H 0.5870 0.1734 0.3762 0.025 Uiso 1 1 calc R . . C12 C 0.89428(14) 0.7480(2) 0.40897(12) 0.0232(4) Uani 1 1 d . . . C13 C 0.91977(18) 1.0186(3) 0.37367(15) 0.0360(5) Uani 1 1 d . . . H13A H 0.8898 1.0615 0.4142 0.054 Uiso 1 1 calc R . . H13B H 0.9014 1.0914 0.3274 0.054 Uiso 1 1 calc R . . H13C H 0.9962 1.0127 0.3956 0.054 Uiso 1 1 calc R . . C14 C 0.90164(14) 0.4866(2) 0.33473(11) 0.0233(4) Uani 1 1 d . . . C15 C 1.07057(17) 0.4096(3) 0.33107(15) 0.0385(5) Uani 1 1 d . . . H15A H 1.0734 0.3003 0.3547 0.058 Uiso 1 1 calc R . . H15B H 1.1414 0.4555 0.3443 0.058 Uiso 1 1 calc R . . H15C H 1.0414 0.4014 0.2732 0.058 Uiso 1 1 calc R . . C16 C 0.55830(13) 0.4871(2) 0.34075(11) 0.0193(3) Uani 1 1 d . . . C17 C 0.47770(14) 0.4553(2) 0.27170(11) 0.0214(4) Uani 1 1 d . . . H17 H 0.4915 0.3955 0.2296 0.026 Uiso 1 1 calc R . . C18 C 0.37619(14) 0.5114(2) 0.26437(11) 0.0244(4) Uani 1 1 d . . . H18 H 0.3212 0.4901 0.2171 0.029 Uiso 1 1 calc R . . C19 C 0.35561(15) 0.5977(2) 0.32579(12) 0.0262(4) Uani 1 1 d . . . H19 H 0.2869 0.6374 0.3202 0.031 Uiso 1 1 calc R . . C20 C 0.43524(16) 0.6262(2) 0.39534(12) 0.0266(4) Uani 1 1 d . . . H20 H 0.4210 0.6840 0.4378 0.032 Uiso 1 1 calc R . . C21 C 0.53602(15) 0.5700(2) 0.40292(11) 0.0237(4) Uani 1 1 d . . . H21 H 0.5902 0.5884 0.4510 0.028 Uiso 1 1 calc R . . O1 O 0.94271(12) 0.77733(18) 0.47668(9) 0.0330(3) Uani 1 1 d . . . O2 O 0.87829(11) 0.85573(16) 0.34986(8) 0.0276(3) Uani 1 1 d . . . O3 O 1.00453(10) 0.51569(18) 0.36216(9) 0.0295(3) Uani 1 1 d . . . O4 O 0.86251(11) 0.38880(19) 0.28336(9) 0.0342(3) Uani 1 1 d . . . Br1 Br 0.658403(16) -0.21181(2) 0.598804(12) 0.02703(8) 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 N1 0.0194(7) 0.0222(8) 0.0237(8) 0.0067(6) -0.0014(6) -0.0040(6) C2 0.0216(8) 0.0250(9) 0.0214(9) 0.0029(7) 0.0026(7) -0.0052(7) C3 0.0199(8) 0.0178(8) 0.0226(9) 0.0028(7) 0.0029(7) -0.0021(6) C4 0.0198(8) 0.0212(9) 0.0248(9) 0.0045(7) 0.0034(7) -0.0017(7) C5 0.0195(8) 0.0181(8) 0.0197(8) 0.0026(7) 0.0021(7) -0.0015(6) C6 0.0211(8) 0.0177(8) 0.0200(9) 0.0013(7) 0.0057(7) 0.0012(7) C7 0.0199(8) 0.0219(9) 0.0207(9) 0.0001(7) 0.0036(7) -0.0009(7) C8 0.0243(9) 0.0253(9) 0.0196(8) 0.0026(7) 0.0056(7) 0.0025(7) C9 0.0271(9) 0.0184(8) 0.0214(9) 0.0027(7) 0.0088(7) 0.0004(7) C10 0.0250(8) 0.0204(8) 0.0205(8) -0.0005(7) 0.0061(7) -0.0033(7) C11 0.0223(8) 0.0199(8) 0.0182(8) 0.0002(7) 0.0036(7) -0.0006(7) C12 0.0198(8) 0.0227(9) 0.0268(10) 0.0006(7) 0.0066(7) -0.0016(7) C13 0.0400(11) 0.0193(9) 0.0446(13) -0.0021(9) 0.0062(10) -0.0077(8) C14 0.0236(9) 0.0222(9) 0.0225(9) 0.0038(7) 0.0044(7) -0.0011(7) C15 0.0290(10) 0.0453(13) 0.0454(13) -0.0117(11) 0.0175(9) 0.0005(9) C16 0.0205(8) 0.0149(8) 0.0211(8) 0.0029(7) 0.0040(7) -0.0019(6) C17 0.0241(8) 0.0198(8) 0.0192(8) -0.0003(7) 0.0047(7) -0.0019(7) C18 0.0212(8) 0.0234(9) 0.0252(9) 0.0026(7) 0.0014(7) -0.0024(7) C19 0.0227(9) 0.0222(9) 0.0350(11) 0.0047(8) 0.0104(8) 0.0012(7) C20 0.0315(10) 0.0213(9) 0.0306(10) -0.0029(8) 0.0148(8) -0.0013(7) C21 0.0265(9) 0.0215(9) 0.0217(9) -0.0009(7) 0.0048(7) -0.0032(7) O1 0.0378(8) 0.0298(8) 0.0268(8) -0.0035(6) 0.0023(6) -0.0081(6) O2 0.0316(7) 0.0183(6) 0.0298(7) 0.0016(5) 0.0043(6) -0.0055(5) O3 0.0223(6) 0.0344(8) 0.0330(8) -0.0071(6) 0.0101(6) -0.0026(6) O4 0.0294(7) 0.0333(8) 0.0362(8) -0.0101(6) 0.0043(6) -0.0010(6) Br1 0.03341(12) 0.02267(11) 0.02402(12) 0.00583(7) 0.00693(8) -0.00416(7) _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 N1 C6 1.376(2) . ? N1 C2 1.449(2) . ? N1 C5 1.468(2) . ? C2 C3 1.544(3) . ? C3 C14 1.516(3) . ? C3 C12 1.526(2) . ? C3 C4 1.539(2) . ? C4 C5 1.543(2) . ? C5 C16 1.519(2) . ? C6 C11 1.406(2) . ? C6 C7 1.411(2) . ? C7 C8 1.387(3) . ? C8 C9 1.382(3) . ? C9 C10 1.388(3) . ? C9 Br1 1.9031(18) . ? C10 C11 1.387(3) . ? C12 O1 1.201(2) . ? C12 O2 1.331(2) . ? C13 O2 1.453(2) . ? C14 O4 1.204(2) . ? C14 O3 1.337(2) . ? C15 O3 1.453(3) . ? C16 C17 1.391(2) . ? C16 C21 1.392(3) . ? C17 C18 1.400(3) . ? C18 C19 1.385(3) . ? C19 C20 1.385(3) . ? C20 C21 1.390(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 C6 N1 C2 120.85(15) . . ? C6 N1 C5 124.63(15) . . ? C2 N1 C5 114.05(14) . . ? N1 C2 C3 104.41(14) . . ? C14 C3 C12 111.77(15) . . ? C14 C3 C4 111.32(15) . . ? C12 C3 C4 112.76(15) . . ? C14 C3 C2 108.56(15) . . ? C12 C3 C2 109.10(15) . . ? C4 C3 C2 102.86(14) . . ? C3 C4 C5 105.54(14) . . ? N1 C5 C16 114.93(15) . . ? N1 C5 C4 102.55(14) . . ? C16 C5 C4 108.70(14) . . ? N1 C6 C11 121.69(16) . . ? N1 C6 C7 120.32(16) . . ? C11 C6 C7 117.99(17) . . ? C8 C7 C6 120.90(17) . . ? C9 C8 C7 119.84(17) . . ? C8 C9 C10 120.60(17) . . ? C8 C9 Br1 119.31(14) . . ? C10 C9 Br1 120.09(14) . . ? C11 C10 C9 119.91(17) . . ? C10 C11 C6 120.76(16) . . ? O1 C12 O2 124.07(18) . . ? O1 C12 C3 124.84(18) . . ? O2 C12 C3 111.07(16) . . ? O4 C14 O3 124.14(19) . . ? O4 C14 C3 124.19(17) . . ? O3 C14 C3 111.58(16) . . ? C17 C16 C21 119.28(17) . . ? C17 C16 C5 119.56(16) . . ? C21 C16 C5 120.88(16) . . ? C16 C17 C18 119.89(17) . . ? C19 C18 C17 120.27(17) . . ? C20 C19 C18 119.93(18) . . ? C19 C20 C21 119.93(18) . . ? C20 C21 C16 120.66(17) . . ? C12 O2 C13 114.74(16) . . ? C14 O3 C15 115.58(16) . . ? 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 C6 N1 C2 C3 160.73(17) . . . . ? C5 N1 C2 C3 -11.8(2) . . . . ? N1 C2 C3 C14 -90.98(17) . . . . ? N1 C2 C3 C12 146.99(15) . . . . ? N1 C2 C3 C4 27.06(19) . . . . ? C14 C3 C4 C5 83.18(18) . . . . ? C12 C3 C4 C5 -150.27(16) . . . . ? C2 C3 C4 C5 -32.90(19) . . . . ? C6 N1 C5 C16 61.4(2) . . . . ? C2 N1 C5 C16 -126.47(17) . . . . ? C6 N1 C5 C4 179.13(17) . . . . ? C2 N1 C5 C4 -8.7(2) . . . . ? C3 C4 C5 N1 25.80(19) . . . . ? C3 C4 C5 C16 147.89(15) . . . . ? C2 N1 C6 C11 -170.36(18) . . . . ? C5 N1 C6 C11 1.3(3) . . . . ? C2 N1 C6 C7 10.6(3) . . . . ? C5 N1 C6 C7 -177.75(17) . . . . ? N1 C6 C7 C8 179.19(17) . . . . ? C11 C6 C7 C8 0.1(3) . . . . ? C6 C7 C8 C9 0.2(3) . . . . ? C7 C8 C9 C10 0.1(3) . . . . ? C7 C8 C9 Br1 -179.45(14) . . . . ? C8 C9 C10 C11 -0.6(3) . . . . ? Br1 C9 C10 C11 178.93(14) . . . . ? C9 C10 C11 C6 0.9(3) . . . . ? N1 C6 C11 C10 -179.70(17) . . . . ? C7 C6 C11 C10 -0.6(3) . . . . ? C14 C3 C12 O1 -105.0(2) . . . . ? C4 C3 C12 O1 128.7(2) . . . . ? C2 C3 C12 O1 15.1(3) . . . . ? C14 C3 C12 O2 76.29(19) . . . . ? C4 C3 C12 O2 -50.0(2) . . . . ? C2 C3 C12 O2 -163.64(15) . . . . ? C12 C3 C14 O4 -152.32(19) . . . . ? C4 C3 C14 O4 -25.2(3) . . . . ? C2 C3 C14 O4 87.3(2) . . . . ? C12 C3 C14 O3 31.0(2) . . . . ? C4 C3 C14 O3 158.11(15) . . . . ? C2 C3 C14 O3 -89.37(18) . . . . ? N1 C5 C16 C17 -145.69(16) . . . . ? C4 C5 C16 C17 100.08(19) . . . . ? N1 C5 C16 C21 40.4(2) . . . . ? C4 C5 C16 C21 -73.8(2) . . . . ? C21 C16 C17 C18 2.1(3) . . . . ? C5 C16 C17 C18 -171.84(16) . . . . ? C16 C17 C18 C19 -0.4(3) . . . . ? C17 C18 C19 C20 -1.2(3) . . . . ? C18 C19 C20 C21 0.9(3) . . . . ? C19 C20 C21 C16 0.9(3) . . . . ? C17 C16 C21 C20 -2.4(3) . . . . ? C5 C16 C21 C20 171.47(17) . . . . ? O1 C12 O2 C13 -3.0(3) . . . . ? C3 C12 O2 C13 175.67(16) . . . . ? O4 C14 O3 C15 -5.5(3) . . . . ? C3 C14 O3 C15 171.22(17) . . . . ? _diffrn_measured_fraction_theta_max 0.997 _diffrn_reflns_theta_full 75.00 _diffrn_measured_fraction_theta_full 1.000 _refine_diff_density_max 0.539 _refine_diff_density_min -0.621 _refine_diff_density_rms 0.064 _iucr_refine_instructions_details ; TITL varge in P2(1)/c CELL 1.54184 13.356878 8.157073 17.617826 90.0000 107.1564 90.0000 ZERR 4.00 0.0002 0.00012 0.0003 0.0000 0.0009 0.0000 LATT 1 SYMM -x, y+1/2,-z+1/2 SFAC C H N O Br UNIT 80.00 80.00 4.00 16.00 4.00 TEMP -173 SIZE 0.2 0.1 0.04 FMAP 2 PLAN 10 L.S. 4 ACTA 150 CONF WGHT 0.038900 1.320500 FVAR 4.35616 N1 3 0.737011 0.391224 0.422016 11.00000 0.01939 0.02224 = 0.02374 0.00666 -0.00139 -0.00399 C2 1 0.833570 0.482963 0.451606 11.00000 0.02163 0.02499 = 0.02145 0.00291 0.00256 -0.00520 AFIX 23 H2A 2 0.894297 0.408197 0.470097 11.00000 -1.20000 H2B 2 0.830877 0.555272 0.496092 11.00000 -1.20000 AFIX 0 C3 1 0.841076 0.584798 0.379592 11.00000 0.01991 0.01778 = 0.02258 0.00284 0.00291 -0.00205 C4 1 0.725598 0.604958 0.330449 11.00000 0.01976 0.02115 = 0.02482 0.00454 0.00341 -0.00166 AFIX 23 H4A 2 0.719453 0.618648 0.273418 11.00000 -1.20000 H4B 2 0.694282 0.701783 0.348610 11.00000 -1.20000 AFIX 0 C5 1 0.670470 0.446289 0.344097 11.00000 0.01952 0.01810 = 0.01972 0.00261 0.00213 -0.00154 AFIX 13 H5 2 0.671305 0.363381 0.302477 11.00000 -1.20000 AFIX 0 C6 1 0.718836 0.253215 0.460839 11.00000 0.02114 0.01765 = 0.01997 0.00128 0.00568 0.00117 C7 1 0.785506 0.213785 0.536977 11.00000 0.01992 0.02189 = 0.02070 0.00007 0.00362 -0.00087 AFIX 43 H7 2 0.843658 0.282464 0.561023 11.00000 -1.20000 AFIX 0 C8 1 0.767297 0.076160 0.577172 11.00000 0.02427 0.02526 = 0.01965 0.00259 0.00559 0.00245 AFIX 43 H8 2 0.812666 0.051105 0.628463 11.00000 -1.20000 AFIX 0 C9 1 0.683003 -0.024456 0.542446 11.00000 0.02712 0.01843 = 0.02136 0.00268 0.00884 0.00040 C10 1 0.616248 0.010775 0.467466 11.00000 0.02500 0.02037 = 0.02045 -0.00054 0.00613 -0.00333 AFIX 43 H10 2 0.558878 -0.059657 0.443814 11.00000 -1.20000 AFIX 0 C11 1 0.633432 0.148924 0.427144 11.00000 0.02229 0.01986 = 0.01819 0.00018 0.00364 -0.00063 AFIX 43 H11 2 0.586976 0.173391 0.376174 11.00000 -1.20000 AFIX 0 C12 1 0.894278 0.747964 0.408972 11.00000 0.01980 0.02273 = 0.02684 0.00063 0.00660 -0.00157 C13 1 0.919769 1.018584 0.373675 11.00000 0.04001 0.01932 = 0.04462 -0.00210 0.00621 -0.00771 AFIX 137 H13A 2 0.889750 1.061453 0.414156 11.00000 -1.50000 H13B 2 0.901361 1.091417 0.327377 11.00000 -1.50000 H13C 2 0.996180 1.012739 0.395552 11.00000 -1.50000 AFIX 0 C14 1 0.901635 0.486647 0.334728 11.00000 0.02358 0.02218 = 0.02248 0.00380 0.00442 -0.00113 C15 1 1.070570 0.409592 0.331067 11.00000 0.02904 0.04528 = 0.04545 -0.01172 0.01750 0.00048 AFIX 137 H15A 2 1.073385 0.300280 0.354685 11.00000 -1.50000 H15B 2 1.141431 0.455534 0.344325 11.00000 -1.50000 H15C 2 1.041425 0.401418 0.273225 11.00000 -1.50000 AFIX 0 C16 1 0.558296 0.487124 0.340745 11.00000 0.02047 0.01491 = 0.02111 0.00289 0.00404 -0.00187 C17 1 0.477695 0.455263 0.271703 11.00000 0.02407 0.01979 = 0.01918 -0.00030 0.00474 -0.00193 AFIX 43 H17 2 0.491468 0.395537 0.229579 11.00000 -1.20000 AFIX 0 C18 1 0.376189 0.511360 0.264370 11.00000 0.02116 0.02337 = 0.02524 0.00264 0.00142 -0.00237 AFIX 43 H18 2 0.321224 0.490100 0.217073 11.00000 -1.20000 AFIX 0 C19 1 0.355606 0.597705 0.325788 11.00000 0.02266 0.02225 = 0.03504 0.00472 0.01038 0.00123 AFIX 43 H19 2 0.286934 0.637369 0.320212 11.00000 -1.20000 AFIX 0 C20 1 0.435239 0.626161 0.395338 11.00000 0.03152 0.02130 = 0.03059 -0.00286 0.01484 -0.00130 AFIX 43 H20 2 0.421032 0.683987 0.437822 11.00000 -1.20000 AFIX 0 C21 1 0.536015 0.570004 0.402923 11.00000 0.02651 0.02146 = 0.02174 -0.00087 0.00478 -0.00320 AFIX 43 H21 2 0.590205 0.588380 0.451018 11.00000 -1.20000 AFIX 0 O1 4 0.942708 0.777333 0.476680 11.00000 0.03779 0.02975 = 0.02678 -0.00355 0.00228 -0.00810 O2 4 0.878285 0.855726 0.349864 11.00000 0.03164 0.01834 = 0.02979 0.00156 0.00428 -0.00554 O3 4 1.004529 0.515695 0.362157 11.00000 0.02232 0.03437 = 0.03301 -0.00707 0.01005 -0.00263 O4 4 0.862506 0.388803 0.283363 11.00000 0.02941 0.03330 = 0.03624 -0.01009 0.00426 -0.00098 BR1 5 0.658403 -0.211814 0.598804 11.00000 0.03341 0.02267 = 0.02402 0.00583 0.00693 -0.00416 HKLF 4 ; # end of cif file