# CIF Copied by cif2cif, version 0.0.8 - beta ( 2 Apr 98) data_global _publ_requested_journal J.Am.Chem.Soc. _publ_contact_author_name 'Christian Nilewski' _publ_contact_author_address ;ETH Zurich Laboratory of Organic Chemistry HCI H330 Wolfgang-Pauli-Strasse 10 8093 Zurich ; _publ_contact_author_email cnilewski@org.chem.ethz.ch _publ_contact_author_phone ' +41 44 632 29 43' _publ_contact_author_fax ' +41 44 632 13 28' loop_ _publ_author_name _publ_author_address 'Nilewski, C' ;ETH Zurich Laboratory of Organic Chemistry HCI H330 Wolfgang-Pauli-Strasse 10 8093 Zurich ; 'Geisser, R. W.' ;ETH Zurich Laboratory of Organic Chemistry HCI G330 Wolfgang-Pauli-Strasse 10 8093 Zurich ; 'Ebert, M.-O.' ;ETH Zurich Laboratory of Organic Chemistry HCI D317 Wolfgang-Pauli-Strasse 10 8093 Zurich ; 'Carreira, E. M.' ;ETH Zurich Laboratory of Organic Chemistry HCI H335 Wolfgang-Pauli-Strasse 10 8093 Zurich ; _audit_creation_method maXus _publ_section_title ; Crystal and molecular structure of ca010408 ; _publ_section_abstract ; We present the crystal and molecular structure of ca010408 ; _publ_section_comment ; The study of the titled structure was undertaken to establish its three dimensional structure. Geometries are tabulated below. All diagrams and calculations were performed using maXus (Bruker Nonius, Delft & MacScience, Japan). ; _publ_section_synopsis ; ; _publ_section_exptl_prep ; ; _publ_section_exptl_refinement ; ; _publ_section_figure_captions ; ; _publ_section_acknowledgements ; ; _chemical_compound_source 'Carreira laboratory' _exptl_crystal_description needle _exptl_crystal_size_max .4 _exptl_crystal_size_mid .02 _exptl_crystal_size_min .01 _exptl_crystal_F_000 456.0 _exptl_crystal_colour Colourless _cell_measurement_temperature 203 _refine_ls_hydrogen_treatment refall # Submission details _diffrn_measurement_device KappaCCD _computing_data_collection KappaCCD _computing_data_reduction 'Denzo and Scalepak (Otwinowski & Minor, 1997)' _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_reflns_limit_h_min -8 _diffrn_reflns_limit_h_max 8 _diffrn_reflns_limit_k_min -16 _diffrn_reflns_limit_k_max 16 _diffrn_reflns_limit_l_min -15 _diffrn_reflns_limit_l_max 16 loop_ _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_wavelength_id all _diffrn_orient_matrix_type X=UH _diffrn_orient_matrix_UB_11 0.15195 _diffrn_orient_matrix_UB_12 0.05918 _diffrn_orient_matrix_UB_13 0.02980 _diffrn_orient_matrix_UB_21 0.01678 _diffrn_orient_matrix_UB_22 -0.04406 _diffrn_orient_matrix_UB_23 -0.06347 _diffrn_orient_matrix_UB_31 -0.02988 _diffrn_orient_matrix_UB_32 0.05913 _diffrn_orient_matrix_UB_33 -0.04301 _cell_formula_units_Z 4 _exptl_crystal_density_diffrn 1.476 _exptl_crystal_density_method 'not measured' _exptl_special_details ; ? ; _chemical_formula_weight 221.511 _diffrn_radiation_type ' MoK\a' loop_ _symmetry_equiv_pos_as_xyz +X,+Y,+Z -X,-Y,-Z _symmetry_space_group_name_H-M 'P -1 ' _symmetry_cell_setting Triclinic _chemical_formula_moiety 'C6 H11 Cl3 O2 ' _chemical_formula_sum 'C6 H11 Cl3 O2 ' _chemical_name_systematic ; ? ; _cell_length_a 6.2122(4) _cell_length_b 12.8417(9) _cell_length_c 12.9157(9) _cell_angle_alpha 84.887(3) _cell_angle_beta 79.116(3) _cell_angle_gamma 80.662(3) _cell_volume 996.59(12) _diffrn_reflns_number 7478 _diffrn_reflns_theta_max 27.47 _diffrn_reflns_theta_min 3.22 _diffrn_reflns_theta_full 27.47 _cell_measurement_reflns_used 18113 _cell_measurement_theta_min 2.910 _cell_measurement_theta_max 27.485 _diffrn_measurement_method CCD _computing_cell_refinement 'HKL Scalepack (Otwinowski & Minor 1997)' _diffrn_reflns_av_R_equivalents 0.067 _computing_structure_solution 'SIR97(Altomare et al., J. Appl. Cryst.,1999)' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _exptl_absorpt_correction_type none _exptl_absorpt_correction_T_min ? _exptl_absorpt_correction_T_max ? 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' Cl Cl 0.1484 0.1585 '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' _exptl_absorpt_coefficient_mu 0.873 _reflns_number_total 4503 _reflns_number_gt 3112 _reflns_threshold_expression >2sigma(I) _computing_structure_refinement 'SHELXL-97 (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^)+ (0.1000P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 4503 _refine_ls_number_parameters 287 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0871 _refine_ls_R_factor_gt 0.0523 _refine_ls_wR_factor_ref 0.1659 _refine_ls_wR_factor_gt 0.1355 _refine_ls_goodness_of_fit_ref 0.904 _refine_ls_restrained_S_all 0.904 _refine_ls_shift/su_max 0.038 _refine_ls_shift/su_mean 0.002 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 Cl8 Cl 0.78834(16) -0.67299(8) 0.77818(8) 0.0379(3) Uani 1 1 d . . . Cl10 Cl 0.39124(14) -0.35768(8) 0.92516(7) 0.0354(2) Uani 1 1 d . . . Cl11 Cl 0.83639(16) -0.34427(8) 1.01835(7) 0.0364(2) Uani 1 1 d . . . Cl19 Cl 0.26068(16) -0.21588(8) 0.67922(7) 0.0362(2) Uani 1 1 d . . . Cl21 Cl 0.30978(15) -0.00110(7) 0.37686(7) 0.0334(2) Uani 1 1 d . . . Cl22 Cl 0.85387(15) -0.08924(9) 0.33158(8) 0.0426(3) Uani 1 1 d . . . O7 O 0.3467(4) -0.5700(3) 0.6942(2) 0.0406(7) Uani 1 1 d . . . O9 O 0.9414(4) -0.4520(2) 0.7276(2) 0.0329(6) Uani 1 1 d . . . O18 O -0.0923(4) -0.2918(3) 0.5732(2) 0.0383(7) Uani 1 1 d . . . O20 O 0.5829(4) -0.2900(2) 0.4626(2) 0.0313(6) Uani 1 1 d . . . C1 C 0.5173(7) -0.5099(3) 0.6980(3) 0.0332(8) Uani 1 1 d . . . C2 C 0.6251(6) -0.5432(3) 0.7944(3) 0.0276(7) Uani 1 1 d . . . C3 C 0.7751(5) -0.4697(3) 0.8176(3) 0.0251(7) Uani 1 1 d . . . C4 C 0.6567(6) -0.3576(3) 0.8422(3) 0.0269(7) Uani 1 1 d . . . C5 C 0.8008(7) -0.2933(3) 0.8866(3) 0.0322(8) Uani 1 1 d . . . C6 C 0.7126(10) -0.1762(4) 0.8873(4) 0.0488(11) Uani 1 1 d . . . C12 C 0.1266(6) -0.2895(3) 0.5159(3) 0.0334(8) Uani 1 1 d . . . C13 C 0.2281(6) -0.1982(3) 0.5422(3) 0.0269(7) Uani 1 1 d . . . C14 C 0.4536(5) -0.1872(3) 0.4740(3) 0.0255(7) Uani 1 1 d . . . C15 C 0.4318(6) -0.1370(3) 0.3627(3) 0.0264(7) Uani 1 1 d . . . C16 C 0.6474(6) -0.1457(3) 0.2835(3) 0.0326(8) Uani 1 1 d . . . C17 C 0.6224(9) -0.0967(4) 0.1742(3) 0.0479(12) Uani 1 1 d . . . H1A H 0.636(7) -0.519(3) 0.633(3) 0.037(11) Uiso 1 1 d . . . H1B H 0.443(6) -0.433(3) 0.707(3) 0.025(9) Uiso 1 1 d . . . H2 H 0.529(8) -0.556(4) 0.855(4) 0.066(16) Uiso 1 1 d . . . H3 H 0.846(7) -0.499(3) 0.879(3) 0.043(12) Uiso 1 1 d . . . H4 H 0.628(6) -0.320(3) 0.781(3) 0.033(10) Uiso 1 1 d . . . H5 H 0.948(7) -0.301(4) 0.845(4) 0.044(12) Uiso 1 1 d . . . H6A H 0.706(8) -0.152(4) 0.812(4) 0.065(15) Uiso 1 1 d . . . H6B H 0.583(9) -0.162(4) 0.934(5) 0.069(17) Uiso 1 1 d . . . H6C H 0.818(9) -0.140(5) 0.912(5) 0.072(18) Uiso 1 1 d . . . H7 H 0.381(8) -0.616(5) 0.644(4) 0.061(16) Uiso 1 1 d . . . H9 H 1.067(13) -0.484(7) 0.726(7) 0.13(3) Uiso 1 1 d . . . H12A H 0.208(7) -0.356(4) 0.532(4) 0.044(12) Uiso 1 1 d . . . H12B H 0.119(7) -0.281(4) 0.443(4) 0.049(13) Uiso 1 1 d . . . H13 H 0.135(6) -0.133(3) 0.536(3) 0.032(10) Uiso 1 1 d . . . H14 H 0.540(5) -0.144(3) 0.506(2) 0.013(8) Uiso 1 1 d . . . H15 H 0.330(6) -0.171(3) 0.334(3) 0.024(9) Uiso 1 1 d . . . H16 H 0.703(6) -0.217(3) 0.276(3) 0.019(9) Uiso 1 1 d . . . H17A H 0.577(8) -0.014(4) 0.173(4) 0.057(14) Uiso 1 1 d . . . H17B H 0.495(9) -0.119(5) 0.153(4) 0.069(18) Uiso 1 1 d . . . H17C H 0.758(8) -0.105(4) 0.125(4) 0.057(14) Uiso 1 1 d . . . H18 H -0.081(7) -0.332(3) 0.621(3) 0.028(11) Uiso 1 1 d . . . H20 H 0.670(9) -0.291(5) 0.491(4) 0.060(18) 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 Cl8 0.0435(5) 0.0298(5) 0.0401(5) -0.0058(4) -0.0099(4) 0.0001(4) Cl10 0.0255(4) 0.0462(6) 0.0309(4) -0.0057(4) 0.0002(3) 0.0007(4) Cl11 0.0371(5) 0.0447(6) 0.0290(4) -0.0012(4) -0.0092(4) -0.0072(4) Cl19 0.0422(5) 0.0414(5) 0.0247(4) -0.0007(4) -0.0053(4) -0.0068(4) Cl21 0.0338(5) 0.0291(5) 0.0346(5) -0.0005(4) -0.0035(4) -0.0008(4) Cl22 0.0284(5) 0.0462(6) 0.0526(6) -0.0029(5) -0.0019(4) -0.0097(4) O7 0.0249(13) 0.0514(18) 0.0480(16) -0.0204(14) -0.0074(12) -0.0029(12) O9 0.0260(13) 0.0359(15) 0.0314(13) 0.0000(11) 0.0043(10) -0.0007(11) O18 0.0278(14) 0.0500(18) 0.0364(15) 0.0143(14) -0.0070(11) -0.0113(12) O20 0.0280(13) 0.0293(14) 0.0365(14) -0.0041(11) -0.0091(11) 0.0010(11) C1 0.035(2) 0.035(2) 0.0319(19) -0.0048(16) -0.0118(16) -0.0036(16) C2 0.0291(17) 0.0275(18) 0.0265(17) -0.0055(14) -0.0050(14) -0.0031(14) C3 0.0207(16) 0.0306(18) 0.0225(16) 0.0008(14) -0.0006(13) -0.0046(13) C4 0.0259(17) 0.0291(18) 0.0239(16) -0.0012(14) -0.0017(13) -0.0019(14) C5 0.040(2) 0.033(2) 0.0230(16) -0.0017(14) -0.0001(15) -0.0084(16) C6 0.078(4) 0.030(2) 0.038(2) -0.0010(18) -0.009(2) -0.010(2) C12 0.0293(19) 0.044(2) 0.0282(18) -0.0011(17) -0.0019(15) -0.0126(17) C13 0.0283(17) 0.0290(18) 0.0212(15) 0.0028(14) -0.0031(13) -0.0010(14) C14 0.0233(16) 0.0256(18) 0.0280(17) -0.0030(14) -0.0050(13) -0.0034(14) C15 0.0263(17) 0.0256(18) 0.0272(17) -0.0012(14) -0.0045(14) -0.0045(14) C16 0.037(2) 0.030(2) 0.0300(18) -0.0040(15) -0.0022(15) -0.0052(16) C17 0.054(3) 0.056(3) 0.027(2) 0.0063(19) 0.0053(19) -0.007(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 Cl8 C2 1.812(4) . ? Cl10 C4 1.789(3) . ? Cl11 C5 1.808(4) . ? Cl19 C13 1.809(3) . ? Cl21 C15 1.797(4) . ? Cl22 C16 1.800(4) . ? O7 C1 1.418(5) . ? O9 C3 1.430(4) . ? O18 C12 1.424(4) . ? O20 C14 1.434(4) . ? C1 C2 1.520(5) . ? C2 C3 1.513(5) . ? C3 C4 1.538(5) . ? C4 C5 1.527(5) . ? C5 C6 1.514(6) . ? C12 C13 1.509(6) . ? C13 C14 1.528(5) . ? C14 C15 1.543(5) . ? C15 C16 1.519(5) . ? C16 C17 1.518(5) . ? O7 H7 0.89(6) . ? O9 H9 0.82(8) . ? O18 H18 0.78(4) . ? O20 H20 0.71(5) . ? C1 H1A 1.01(4) . ? C1 H1B 1.03(4) . ? C2 H2 0.91(5) . ? C3 H3 0.99(4) . ? C4 H4 0.92(4) . ? C5 H5 0.96(4) . ? C6 H6A 1.00(5) . ? C6 H6B 0.92(5) . ? C6 H6C 0.97(6) . ? C12 H12A 0.94(5) . ? C12 H12B 0.95(5) . ? C13 H13 0.94(4) . ? C14 H14 0.99(4) . ? C15 H15 0.97(4) . ? C16 H16 0.94(4) . ? C17 H17A 1.05(5) . ? C17 H17B 0.98(6) . ? C17 H17C 0.95(5) . ? 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 O7 C1 C2 111.5(3) . . ? C3 C2 C1 115.3(3) . . ? C3 C2 Cl8 107.6(2) . . ? C1 C2 Cl8 109.4(2) . . ? O9 C3 C2 111.3(3) . . ? O9 C3 C4 103.3(3) . . ? C2 C3 C4 114.2(3) . . ? C5 C4 C3 112.4(3) . . ? C5 C4 Cl10 111.5(2) . . ? C3 C4 Cl10 112.6(3) . . ? C6 C5 C4 113.5(4) . . ? C6 C5 Cl11 109.8(3) . . ? C4 C5 Cl11 110.6(3) . . ? O18 C12 C13 112.6(3) . . ? C12 C13 C14 113.7(3) . . ? C12 C13 Cl19 108.8(3) . . ? C14 C13 Cl19 108.6(2) . . ? O20 C14 C13 109.0(3) . . ? O20 C14 C15 108.1(3) . . ? C13 C14 C15 112.1(3) . . ? C16 C15 C14 114.7(3) . . ? C16 C15 Cl21 110.9(3) . . ? C14 C15 Cl21 107.5(2) . . ? C17 C16 C15 113.9(3) . . ? C17 C16 Cl22 109.7(3) . . ? C15 C16 Cl22 110.8(3) . . ? C1 O7 H7 114(4) . . ? C3 O9 H9 119(6) . . ? C12 O18 H18 106(3) . . ? C14 O20 H20 106(5) . . ? O7 C1 H1A 110(3) . . ? C2 C1 H1A 109(2) . . ? O7 C1 H1B 107(2) . . ? C2 C1 H1B 106(2) . . ? H1A C1 H1B 113(3) . . ? C3 C2 H2 108(4) . . ? C1 C2 H2 115(3) . . ? Cl8 C2 H2 100(3) . . ? O9 C3 H3 110(2) . . ? C2 C3 H3 110(3) . . ? C4 C3 H3 108(2) . . ? C5 C4 H4 105(3) . . ? C3 C4 H4 110(3) . . ? Cl10 C4 H4 105(2) . . ? C6 C5 H5 108(3) . . ? C4 C5 H5 110(3) . . ? Cl11 C5 H5 105(3) . . ? C5 C6 H6A 106(3) . . ? C5 C6 H6B 113(4) . . ? H6A C6 H6B 116(4) . . ? C5 C6 H6C 109(3) . . ? H6A C6 H6C 109(5) . . ? H6B C6 H6C 105(5) . . ? O18 C12 H12A 106(3) . . ? C13 C12 H12A 113(3) . . ? O18 C12 H12B 108(3) . . ? C13 C12 H12B 108(3) . . ? H12A C12 H12B 111(4) . . ? C12 C13 H13 112(3) . . ? C14 C13 H13 108(3) . . ? Cl19 C13 H13 106(2) . . ? O20 C14 H14 107.1(18) . . ? C13 C14 H14 112.8(18) . . ? C15 C14 H14 107.5(19) . . ? C16 C15 H15 107(2) . . ? C14 C15 H15 110(2) . . ? Cl21 C15 H15 107(2) . . ? C17 C16 H16 107(2) . . ? C15 C16 H16 108(2) . . ? Cl22 C16 H16 106(2) . . ? C16 C17 H17A 113(3) . . ? C16 C17 H17B 110(3) . . ? H17A C17 H17B 102(4) . . ? C16 C17 H17C 113(3) . . ? H17A C17 H17C 103(4) . . ? H17B C17 H17C 116(4) . . ? 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 O7 C1 C2 C3 -168.0(3) . . . . ? O7 C1 C2 Cl8 70.7(3) . . . . ? C1 C2 C3 O9 -54.2(4) . . . . ? Cl8 C2 C3 O9 68.1(3) . . . . ? C1 C2 C3 C4 62.2(4) . . . . ? Cl8 C2 C3 C4 -175.4(2) . . . . ? O9 C3 C4 C5 -70.6(3) . . . . ? C2 C3 C4 C5 168.4(3) . . . . ? O9 C3 C4 Cl10 162.4(2) . . . . ? C2 C3 C4 Cl10 41.4(4) . . . . ? C3 C4 C5 C6 166.4(3) . . . . ? Cl10 C4 C5 C6 -66.1(4) . . . . ? C3 C4 C5 Cl11 -69.8(3) . . . . ? Cl10 C4 C5 Cl11 57.7(3) . . . . ? O18 C12 C13 C14 -174.2(3) . . . . ? O18 C12 C13 Cl19 64.7(4) . . . . ? C12 C13 C14 O20 -42.6(4) . . . . ? Cl19 C13 C14 O20 78.7(3) . . . . ? C12 C13 C14 C15 77.1(4) . . . . ? Cl19 C13 C14 C15 -161.7(2) . . . . ? O20 C14 C15 C16 -46.9(4) . . . . ? C13 C14 C15 C16 -167.1(3) . . . . ? O20 C14 C15 Cl21 -170.7(2) . . . . ? C13 C14 C15 Cl21 69.1(3) . . . . ? C14 C15 C16 C17 179.6(4) . . . . ? Cl21 C15 C16 C17 -58.5(4) . . . . ? C14 C15 C16 Cl22 -56.1(4) . . . . ? Cl21 C15 C16 Cl22 65.9(3) . . . . ? _diffrn_measured_fraction_theta_max 0.991 _diffrn_measured_fraction_theta_full 0.991 _refine_diff_density_max 0.358 _refine_diff_density_min -0.537 _refine_diff_density_rms 0.089 _publ_section_references ; Mackay, S., Gilmore, C. J.,Edwards, C., Stewart, N. & Shankland, K. (1999). maXus Computer Program for the Solution and Refinement of Crystal Structures. Bruker Nonius, The Netherlands, MacScience, Japan & The University of Glasgow. Johnson, C. K. (1976). ORTEP-II. A Fortran Thermal-Ellipsoid Plot Program. Report ORNL-5138. Oak Ridge National Laboratory, Oak Ridge, Tennessee, USA. Otwinowski, Z. and Minor, W, (1997). In Methods in Enzymology, 276, edited by C.W. Carter, Jr. & R.M. Sweet pp. 307-326, New York:Academic Press. Altomare, A., Burla, M.C., Camalli, M., Cascarano, G.L., Giacovazzo, C., Guagliardi, A., Moliterni, A.G.G & Spagna, R. (1999). J. Appl. Cryst. 32, 115-119. Sheldrick, G. M. (1997). SHELXL97. Program for the Refinement of Crystal Structures. University of G\"ottingen, Germany. ;