#------------------------------------------------------------------------------ #$Date: 2008-04-05 11:13:02 +0300 (Sat, 05 Apr 2008) $ #$Revision: 340 $ #$URL: file:///home/coder/svn-repositories/cod/cif/2/2102206.cif $ #------------------------------------------------------------------------------ # # This file is available in the Crystallography Open Database (COD), # http://www.crystallography.net/. The original data for this entry # were provided by IUCr Journals, http://journals.iucr.org/. # # The file may be used within the scientific community so long as # proper attribution is given to the journal article from which the # data were obtained. # data_2102206 loop_ _publ_author_name 'G\"orbitz, Carl Henrik' 'Hersleth, Hans-Petter' _publ_section_title ; Selective solvent inclusion as a tool for mapping molecular properties in crystal structures: a diethylstilbestrol example ; _journal_issue 6 _journal_name_full 'Acta Crystallographica Section B' _journal_page_first 1094 _journal_page_last 1102 _journal_volume 56 _journal_year 2000 _chemical_formula_moiety 'C18 H20 O2,C2 H6 O S' _chemical_formula_sum 'C20 H26 O3 S' _chemical_formula_weight 346.47 _chemical_name_systematic ; diethylstilbestrol dimethylsulfoxide solvate (1/1) ; _symmetry_cell_setting triclinic _symmetry_space_group_name_H-M P-1 _atom_sites_solution_hydrogens geom _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _audit_creation_method SHELXL-97 _cell_angle_alpha 90.975(2) _cell_angle_beta 105.924(2) _cell_angle_gamma 100.892(2) _cell_formula_units_Z 2 _cell_length_a 7.8841(5) _cell_length_b 9.1401(5) _cell_length_c 13.6505(8) _cell_measurement_reflns_used 5718 _cell_measurement_temperature 150(2) _cell_measurement_theta_max 37.9 _cell_measurement_theta_min 2.3 _cell_volume 926.41(9) _computing_cell_refinement 'SAINT (Bruker, 1998)' _computing_data_collection 'SMART (Bruker, 1998)' _computing_data_reduction 'SAINT (Bruker, 1998)' _computing_molecular_graphics 'SHELXTL (Sheldrick, 1997)' _computing_publication_material 'SHELXTL (Sheldrick, 1997)' _computing_structure_refinement 'SHELXTL (Sheldrick, 1997)' _computing_structure_solution 'SHELXTL (Sheldrick, 1997)' _diffrn_ambient_temperature 150(2) _diffrn_detector_area_resol_mean 8.3 _diffrn_measured_fraction_theta_full 0.880 _diffrn_measured_fraction_theta_max 0.880 _diffrn_measurement_device_type 'Siemens SMART CCD diffractometer' _diffrn_measurement_method 'Sets of exposures each taken over 0.3\% \w rotation' _diffrn_radiation_monochromator graphite _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_type MoK\a _diffrn_radiation_wavelength 0.71073 _diffrn_reflns_av_R_equivalents 0.0172 _diffrn_reflns_av_sigmaI/netI 0.0175 _diffrn_reflns_limit_h_max 13 _diffrn_reflns_limit_h_min -12 _diffrn_reflns_limit_k_max 15 _diffrn_reflns_limit_k_min -15 _diffrn_reflns_limit_l_max 23 _diffrn_reflns_limit_l_min -22 _diffrn_reflns_number 14256 _diffrn_reflns_theta_full 37.99 _diffrn_reflns_theta_max 37.99 _diffrn_reflns_theta_min 2.28 _diffrn_standards_decay_% none _exptl_absorpt_coefficient_mu 0.189 _exptl_absorpt_correction_T_max 0.972 _exptl_absorpt_correction_T_min 0.868 _exptl_absorpt_correction_type empirical _exptl_absorpt_process_details 'SADABS (Sheldrick, 1996)' _exptl_crystal_colour colourless _exptl_crystal_density_diffrn 1.242 _exptl_crystal_density_meas 'not measured' _exptl_crystal_density_method 'not measured' _exptl_crystal_description needle _exptl_crystal_F_000 372 _exptl_crystal_size_max 0.75 _exptl_crystal_size_mid 0.35 _exptl_crystal_size_min 0.15 _refine_diff_density_max 0.543 _refine_diff_density_min -0.322 _refine_diff_density_rms 0.066 _refine_ls_extinction_method none _refine_ls_goodness_of_fit_ref 1.065 _refine_ls_hydrogen_treatment mixed _refine_ls_matrix_type full _refine_ls_number_parameters 241 _refine_ls_number_reflns 8871 _refine_ls_number_restraints 0 _refine_ls_restrained_S_all 1.065 _refine_ls_R_factor_all 0.0507 _refine_ls_R_factor_gt 0.0404 _refine_ls_shift/su_max 0.012 _refine_ls_shift/su_mean 0.002 _refine_ls_structure_factor_coef Fsqd _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0658P)^2^+0.1723P] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_gt 0.1110 _refine_ls_wR_factor_ref 0.1214 _reflns_number_gt 7444 _reflns_number_total 8871 _reflns_threshold_expression >2sigma(I) _[local]_cod_data_source_file os0062.cif 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' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' S S 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' 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 O1A O 0.17303(9) 0.11935(8) 0.91369(5) 0.02410(11) Uani 1 1 d . H1A H 0.095(2) 0.1741(17) 0.9150(12) 0.036 Uiso 1 1 d . C1A C 0.32910(9) 0.17555(8) 0.64429(5) 0.01653(11) Uani 1 1 d . C2A C 0.23378(10) 0.27392(8) 0.67516(5) 0.01905(12) Uani 1 1 d . H2A H 0.2035(4) 0.3555(11) 0.6330(6) 0.023 Uiso 1 1 calc R C3A C 0.18111(10) 0.25809(9) 0.76462(6) 0.02015(12) Uani 1 1 d . H3A H 0.1141(9) 0.3271(9) 0.7840(3) 0.024 Uiso 1 1 calc R C4A C 0.22511(10) 0.14272(9) 0.82615(5) 0.01841(12) Uani 1 1 d . C5A C 0.32598(11) 0.04701(9) 0.79942(6) 0.02062(12) Uani 1 1 d . H5A H 0.3599(5) -0.0298(11) 0.8424(6) 0.025 Uiso 1 1 calc R C6A C 0.37698(10) 0.06406(9) 0.70969(6) 0.01943(12) Uani 1 1 d . H6A H 0.4476(9) -0.0030(9) 0.6919(2) 0.023 Uiso 1 1 calc R C7A C 0.37820(9) 0.18665(8) 0.54601(5) 0.01615(11) Uani 1 1 d . C8A C 0.57349(10) 0.18239(9) 0.55545(6) 0.01948(12) Uani 1 1 d . H81A H 0.58827(17) 0.17430(12) 0.4879(6) 0.023 Uiso 1 1 calc R H82B H 0.6017(3) 0.0943(8) 0.5886(3) 0.023 Uiso 1 1 calc R C9A C 0.70720(12) 0.31914(13) 0.61528(8) 0.03227(19) Uani 1 1 d . H91A H 0.8279(12) 0.3077(5) 0.6200(7) 0.048 Uiso 1 1 calc R H92B H 0.6933(10) 0.3284(7) 0.6828(7) 0.048 Uiso 1 1 calc R H93C H 0.6845(9) 0.4072(9) 0.5807(5) 0.048 Uiso 1 1 calc R O1'A O 0.43964(9) 0.24780(8) 0.08184(5) 0.02637(12) Uani 1 1 d . H1'A H 0.354(2) 0.1904(18) 0.0323(13) 0.040 Uiso 1 1 d . C1'A C 0.30326(9) 0.20581(8) 0.35734(5) 0.01625(11) Uani 1 1 d . C2'A C 0.43690(10) 0.32269(8) 0.34443(6) 0.01912(12) Uani 1 1 d . H2'A H 0.4991(9) 0.3946(10) 0.3998(8) 0.023 Uiso 1 1 calc R C3'A C 0.48075(10) 0.33607(9) 0.25239(6) 0.02057(12) Uani 1 1 d . H3'A H 0.5754(13) 0.4187(11) 0.24548(11) 0.025 Uiso 1 1 calc R C4'A C 0.39012(10) 0.23207(9) 0.17016(5) 0.01892(12) Uani 1 1 d . C5'A C 0.25476(10) 0.11557(9) 0.18031(6) 0.01981(12) Uani 1 1 d . H5'A H 0.1937(9) 0.0466(10) 0.1260(8) 0.024 Uiso 1 1 calc R C6'A C 0.21219(10) 0.10379(8) 0.27274(5) 0.01883(12) Uani 1 1 d . H6'A H 0.1148(13) 0.0210(11) 0.27903(10) 0.023 Uiso 1 1 calc R C7'A C 0.25389(9) 0.19111(8) 0.45543(5) 0.01637(11) Uani 1 1 d . C8'A C 0.05348(10) 0.17480(9) 0.44258(6) 0.01997(12) Uani 1 1 d . H83A H 0.0299(2) 0.1523(2) 0.5078(6) 0.024 Uiso 1 1 calc R H84B H -0.0117(6) 0.0904(8) 0.3934(5) 0.024 Uiso 1 1 calc R C9'A C -0.01909(13) 0.31426(12) 0.40619(8) 0.02932(17) Uani 1 1 d . H94A H -0.1499(12) 0.2946(4) 0.3956(7) 0.044 Uiso 1 1 calc R H95B H 0.0076(12) 0.3398(7) 0.3417(7) 0.044 Uiso 1 1 calc R H96C H 0.0384(11) 0.3978(8) 0.4580(6) 0.044 Uiso 1 1 calc R S1B S 0.79897(3) 0.26260(2) -0.021144(17) 0.02585(6) Uani 1 1 d . O1B O 0.95990(11) 0.29463(9) -0.06415(7) 0.03634(17) Uani 1 1 d . C1B C 0.88274(14) 0.33704(13) 0.10853(8) 0.03238(19) Uani 1 1 d . H11B H 0.9681(13) 0.2816(9) 0.1459(4) 0.049 Uiso 1 1 calc R H12B H 0.7848(9) 0.3297(11) 0.1383(4) 0.049 Uiso 1 1 calc R H13B H 0.9403(14) 0.4398(10) 0.11110(10) 0.049 Uiso 1 1 calc R C2B C 0.66923(14) 0.39785(13) -0.07177(8) 0.03256(19) Uani 1 1 d . H21B H 0.6202(12) 0.3773(7) -0.1433(7) 0.049 Uiso 1 1 calc R H22B H 0.7439(8) 0.4944(9) -0.0580(7) 0.049 Uiso 1 1 calc R H23B H 0.5745(12) 0.3939(8) -0.0410(7) 0.049 Uiso 1 1 calc R 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 0.0241(3) 0.0349(3) 0.0171(2) 0.0039(2) 0.00965(19) 0.0095(2) C1A 0.0163(3) 0.0192(3) 0.0147(2) 0.0005(2) 0.00444(19) 0.0050(2) C2A 0.0212(3) 0.0212(3) 0.0164(3) 0.0013(2) 0.0056(2) 0.0080(2) C3A 0.0207(3) 0.0243(3) 0.0176(3) 0.0004(2) 0.0063(2) 0.0086(2) C4A 0.0168(3) 0.0243(3) 0.0143(2) 0.0004(2) 0.0046(2) 0.0043(2) C5A 0.0223(3) 0.0244(3) 0.0178(3) 0.0046(2) 0.0073(2) 0.0086(2) C6A 0.0206(3) 0.0230(3) 0.0175(3) 0.0030(2) 0.0068(2) 0.0088(2) C7A 0.0162(3) 0.0182(3) 0.0149(2) 0.0005(2) 0.00474(19) 0.0053(2) C8A 0.0175(3) 0.0249(3) 0.0182(3) 0.0015(2) 0.0058(2) 0.0082(2) C9A 0.0193(3) 0.0409(5) 0.0330(4) -0.0085(4) 0.0051(3) 0.0016(3) O1'A 0.0248(3) 0.0387(3) 0.0162(2) 0.0025(2) 0.00889(19) 0.0031(2) C1'A 0.0163(3) 0.0184(3) 0.0145(2) 0.0015(2) 0.00435(19) 0.0045(2) C2'A 0.0201(3) 0.0194(3) 0.0173(3) 0.0004(2) 0.0058(2) 0.0020(2) C3'A 0.0208(3) 0.0223(3) 0.0183(3) 0.0027(2) 0.0065(2) 0.0021(2) C4'A 0.0186(3) 0.0245(3) 0.0154(3) 0.0034(2) 0.0059(2) 0.0068(2) C5'A 0.0201(3) 0.0232(3) 0.0155(3) -0.0008(2) 0.0046(2) 0.0036(2) C6'A 0.0185(3) 0.0209(3) 0.0161(3) 0.0002(2) 0.0048(2) 0.0020(2) C7'A 0.0159(3) 0.0182(3) 0.0154(2) 0.0011(2) 0.00496(19) 0.0038(2) C8'A 0.0157(3) 0.0259(3) 0.0182(3) 0.0018(2) 0.0050(2) 0.0033(2) C9'A 0.0243(4) 0.0377(4) 0.0307(4) 0.0094(3) 0.0091(3) 0.0155(3) S1B 0.02927(11) 0.02513(9) 0.02839(10) 0.00440(7) 0.01414(8) 0.00920(7) O1B 0.0397(4) 0.0421(4) 0.0411(4) 0.0080(3) 0.0271(3) 0.0184(3) C1B 0.0281(4) 0.0457(5) 0.0274(4) 0.0049(4) 0.0111(3) 0.0120(4) C2B 0.0299(4) 0.0396(5) 0.0349(4) 0.0139(4) 0.0146(3) 0.0145(4) loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance O1A C4A 1.3735(9) O1A H1A 0.869(16) C1A C2A 1.4025(10) C1A C6A 1.4033(10) C1A C7A 1.4949(9) C2A C3A 1.3950(10) C2A H2A 0.9752 C3A C4A 1.3951(11) C3A H3A 0.9709 C4A C5A 1.3937(11) C5A C6A 1.3925(10) C5A H5A 0.9525 C6A H6A 0.9710 C7A C7'A 1.3575(10) C7A C8A 1.5174(10) C8A C9A 1.5281(13) C8A H81A 0.9634 C8A H82B 0.9634 C9A H91A 0.9613 C9A H92B 0.9613 C9A H93C 0.9613 O1'A C4'A 1.3674(9) O1'A H1'A 0.889(17) C1'A C2'A 1.4019(10) C1'A C6'A 1.4050(10) C1'A C7'A 1.4950(9) C2'A C3'A 1.3930(10) C2'A H2'A 0.9496 C3'A C4'A 1.3932(11) C3'A H3'A 0.9822 C4'A C5'A 1.3959(11) C5'A C6'A 1.3927(10) C5'A H5'A 0.9233 C6'A H6'A 0.9943 C7'A C8'A 1.5190(10) C8'A C9'A 1.5297(12) C8'A H83A 0.9762 C8'A H84B 0.9762 C9'A H94A 0.9816 C9'A H95B 0.9817 C9'A H96C 0.9816 S1B O1B 1.5212(8) S1B C2B 1.7807(10) S1B C1B 1.7833(11) C1B H11B 0.9586 C1B H12B 0.9586 C1B H13B 0.9586 C2B H21B 0.9478 C2B H22B 0.9478 C2B H23B 0.9478 loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle C4A O1A H1A 108.4(10) C2A C1A C6A 117.16(6) C2A C1A C7A 122.23(6) C6A C1A C7A 120.62(6) C3A C2A C1A 121.73(7) C3A C2A H2A 119.1 C1A C2A H2A 119.1 C2A C3A C4A 119.71(7) C2A C3A H3A 120.1 C4A C3A H3A 120.1 O1A C4A C5A 117.94(7) O1A C4A C3A 122.31(7) C5A C4A C3A 119.76(7) C6A C5A C4A 119.77(7) C6A C5A H5A 120.1 C4A C5A H5A 120.1 C5A C6A C1A 121.79(7) C5A C6A H6A 119.1 C1A C6A H6A 119.1 C7'A C7A C1A 121.92(6) C7'A C7A C8A 123.37(6) C1A C7A C8A 114.60(6) C7A C8A C9A 113.90(6) C7A C8A H81A 108.8 C9A C8A H81A 108.8 C7A C8A H82B 108.8 C9A C8A H82B 108.8 H81A C8A H82B 107.7 C8A C9A H91A 109.5 C8A C9A H92B 109.5 H91A C9A H92B 109.5 C8A C9A H93C 109.5 H91A C9A H93C 109.5 H92B C9A H93C 109.5 C4'A O1'A H1'A 107.9(10) C2'A C1'A C6'A 117.23(6) C2'A C1'A C7'A 122.14(6) C6'A C1'A C7'A 120.60(6) C3'A C2'A C1'A 121.67(7) C3'A C2'A H2'A 119.2 C1'A C2'A H2'A 119.2 C2'A C3'A C4'A 119.91(7) C2'A C3'A H3'A 120.0 C4'A C3'A H3'A 120.0 O1'A C4'A C3'A 118.00(7) O1'A C4'A C5'A 122.27(7) C3'A C4'A C5'A 119.72(7) C6'A C5'A C4'A 119.71(7) C6'A C5'A H5'A 120.1 C4'A C5'A H5'A 120.1 C5'A C6'A C1'A 121.74(7) C5'A C6'A H6'A 119.1 C1'A C6'A H6'A 119.1 C7A C7'A C1'A 122.05(6) C7A C7'A C8'A 124.16(6) C1'A C7'A C8'A 113.73(6) C7'A C8'A C9'A 113.47(7) C7'A C8'A H83A 108.9 C9'A C8'A H83A 108.9 C7'A C8'A H84B 108.9 C9'A C8'A H84B 108.9 H83A C8'A H84B 107.7 C8'A C9'A H94A 109.5 C8'A C9'A H95B 109.5 H94A C9'A H95B 109.5 C8'A C9'A H96C 109.5 H94A C9'A H96C 109.5 H95B C9'A H96C 109.5 O1B S1B C2B 104.50(5) O1B S1B C1B 105.25(5) C2B S1B C1B 98.84(5) S1B C1B H11B 109.5 S1B C1B H12B 109.5 H11B C1B H12B 109.5 S1B C1B H13B 109.5 H11B C1B H13B 109.5 H12B C1B H13B 109.5 S1B C2B H21B 109.5 S1B C2B H22B 109.5 H21B C2B H22B 109.5 S1B C2B H23B 109.5 H21B C2B H23B 109.5 H22B C2B H23B 109.5 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 C6A C1A C2A C3A -2.89(11) C7A C1A C2A C3A 176.85(7) C1A C2A C3A C4A 0.64(12) C2A C3A C4A O1A -178.33(7) C2A C3A C4A C5A 1.94(12) O1A C4A C5A C6A 178.11(7) C3A C4A C5A C6A -2.16(12) C4A C5A C6A C1A -0.20(12) C2A C1A C6A C5A 2.67(11) C7A C1A C6A C5A -177.07(7) C2A C1A C7A C7'A -52.18(10) C6A C1A C7A C7'A 127.54(8) C2A C1A C7A C8A 131.54(7) C6A C1A C7A C8A -48.74(9) C7'A C7A C8A C9A 116.36(8) C1A C7A C8A C9A -67.42(9) C6'A C1'A C2'A C3'A -1.26(11) C7'A C1'A C2'A C3'A -179.42(7) C1'A C2'A C3'A C4'A 0.35(12) C2'A C3'A C4'A O1'A -178.83(7) C2'A C3'A C4'A C5'A 0.49(11) O1'A C4'A C5'A C6'A 178.91(7) C3'A C4'A C5'A C6'A -0.38(11) C4'A C5'A C6'A C1'A -0.58(11) C2'A C1'A C6'A C5'A 1.37(11) C7'A C1'A C6'A C5'A 179.57(7) C1A C7A C7'A C1'A 178.54(6) C8A C7A C7'A C1'A -5.51(11) C1A C7A C7'A C8'A -4.39(11) C8A C7A C7'A C8'A 171.56(7) C2'A C1'A C7'A C7A -54.86(10) C6'A C1'A C7'A C7A 127.04(8) C2'A C1'A C7'A C8'A 127.79(7) C6'A C1'A C7'A C8'A -50.31(9) C7A C7'A C8'A C9'A 116.47(8) C1'A C7'A C8'A C9'A -66.24(8) loop_ _geom_hbond_atom_site_label_D _geom_hbond_atom_site_label_H _geom_hbond_atom_site_label_A _geom_hbond_distance_DH _geom_hbond_distance_HA _geom_hbond_distance_DA _geom_hbond_angle_DHA _geom_hbond_publ_flag _geom_hbond_site_symmetry_A O1A H1A O1B 0.869(16) 1.738(16) 2.6004(10) 171.2(16) y 1_456 O1'A H1'A O1A 0.889(17) 1.852(17) 2.7191(9) 164.6(15) y 1_554