#------------------------------------------------------------------------------ #$Date: 2012-02-03 19:16:24 +0200 (Fri, 03 Feb 2012) $ #$Revision: 32112 $ #$URL: file:///home/coder/svn-repositories/cod/cif/2/10/22/2102207.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_2102207 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_coeditor_code OS0062 _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,C3 H7 N O' _chemical_formula_sum 'C21 H27 N O3' _chemical_formula_weight 341.44 _chemical_name_systematic ; diethylstilbestrol N,N-dimethylformamide solvate (1/1) ; _space_group_IT_number 2 _symmetry_cell_setting triclinic _symmetry_space_group_name_Hall '-P 1' _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 91.883(2) _cell_angle_beta 104.036(1) _cell_angle_gamma 104.311(1) _cell_formula_units_Z 2 _cell_length_a 7.6393(1) _cell_length_b 9.9833(3) _cell_length_c 13.3161(1) _cell_measurement_reflns_used 5987 _cell_measurement_temperature 150(2) _cell_measurement_theta_max 38.0 _cell_measurement_theta_min 2.1 _cell_volume 950.00(3) _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 0.873 _diffrn_measured_fraction_theta_max 0.873 _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 0.0135 _diffrn_reflns_av_sigmaI/netI 0.0150 _diffrn_reflns_limit_h_max 12 _diffrn_reflns_limit_h_min -12 _diffrn_reflns_limit_k_max 16 _diffrn_reflns_limit_k_min -17 _diffrn_reflns_limit_l_max 22 _diffrn_reflns_limit_l_min -22 _diffrn_reflns_number 14448 _diffrn_reflns_theta_full 38.02 _diffrn_reflns_theta_max 38.02 _diffrn_reflns_theta_min 2.12 _diffrn_standards_decay_% 0 _exptl_absorpt_coefficient_mu 0.079 _exptl_absorpt_correction_T_max 0.988 _exptl_absorpt_correction_T_min 0.946 _exptl_absorpt_correction_type empirical _exptl_absorpt_process_details 'SADABS (Sheldrick, 1996)' _exptl_crystal_colour colourless _exptl_crystal_density_diffrn 1.194 _exptl_crystal_density_meas 'not measured' _exptl_crystal_density_method 'not measured' _exptl_crystal_description plate _exptl_crystal_F_000 368 _exptl_crystal_size_max 0.70 _exptl_crystal_size_mid 0.65 _exptl_crystal_size_min 0.15 _refine_diff_density_max 0.501 _refine_diff_density_min -0.308 _refine_diff_density_rms 0.050 _refine_ls_extinction_method none _refine_ls_goodness_of_fit_ref 1.035 _refine_ls_hydrogen_treatment mixed _refine_ls_matrix_type full _refine_ls_number_parameters 251 _refine_ls_number_reflns 9040 _refine_ls_number_restraints 0 _refine_ls_restrained_S_all 1.035 _refine_ls_R_factor_all 0.0605 _refine_ls_R_factor_gt 0.0468 _refine_ls_shift/su_max 0.009 _refine_ls_shift/su_mean 0.000 _refine_ls_structure_factor_coef Fsqd _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0839P)^2^+0.1252P] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_gt 0.1334 _refine_ls_wR_factor_ref 0.1467 _reflns_number_gt 7209 _reflns_number_total 9040 _reflns_threshold_expression >2sigma(I) _[local]_cod_data_source_file os0062.cif _[local]_cod_data_source_block ddmf _[local]_cod_cif_authors_sg_H-M P-1 _cod_database_code 2102207 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' N N 0.0061 0.0033 '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 0.59398(9) 0.21122(7) 0.91708(4) 0.03045(13) Uani 1 1 d . H1A H 0.610(2) 0.1215(16) 0.9166(11) 0.046 Uiso 1 1 d . C1A C 0.29205(9) 0.28762(7) 0.62698(5) 0.01889(11) Uani 1 1 d . C2A C 0.35322(11) 0.16662(7) 0.63835(5) 0.02474(13) Uani 1 1 d . H2A H 0.3227(4) 0.0974(8) 0.5760(8) 0.030 Uiso 1 1 calc R C3A C 0.45560(11) 0.13933(8) 0.73396(6) 0.02540(13) Uani 1 1 d . H3A H 0.4964(5) 0.0548(11) 0.73975(9) 0.030 Uiso 1 1 calc R C4A C 0.49859(10) 0.23458(7) 0.82096(5) 0.02146(11) Uani 1 1 d . C5A C 0.44276(10) 0.35758(7) 0.81130(5) 0.02192(12) Uani 1 1 d . H5A H 0.4761(4) 0.4258(8) 0.8713(7) 0.026 Uiso 1 1 calc R C6A C 0.33921(9) 0.38252(7) 0.71556(5) 0.02009(11) Uani 1 1 d . H6A H 0.2977(5) 0.4697(10) 0.70985(8) 0.024 Uiso 1 1 calc R C7A C 0.17017(9) 0.31226(7) 0.52662(5) 0.01900(11) Uani 1 1 d . C8A C -0.01978(10) 0.32404(8) 0.53575(5) 0.02287(12) Uani 1 1 d . H81A H -0.0880(6) 0.3500(2) 0.4691(6) 0.027 Uiso 1 1 calc R H82A H -0.00195(18) 0.3992(6) 0.5908(5) 0.027 Uiso 1 1 calc R C9A C -0.13776(12) 0.18866(10) 0.56176(8) 0.03497(18) Uani 1 1 d . H91A H -0.2550(12) 0.2034(3) 0.5725(7) 0.052 Uiso 1 1 calc R H92A H -0.0674(8) 0.1593(6) 0.6256(7) 0.052 Uiso 1 1 calc R H93A H -0.1669(11) 0.1160(7) 0.5039(6) 0.052 Uiso 1 1 calc R O1'A O -0.22685(11) 0.43255(7) 0.05911(5) 0.03747(16) Uani 1 1 d . H1'A H -0.300(2) 0.3558(18) 0.0199(13) 0.056 Uiso 1 1 d . C1'A C 0.10433(9) 0.34757(7) 0.33765(5) 0.01956(11) Uani 1 1 d . C2'A C -0.06969(10) 0.25545(8) 0.28978(5) 0.02305(12) Uani 1 1 d . H2'A H -0.1131(5) 0.1702(11) 0.3222(4) 0.028 Uiso 1 1 calc R C3'A C -0.18326(10) 0.28155(8) 0.19701(5) 0.02474(13) Uani 1 1 d . H3'A H -0.3060(15) 0.2166(8) 0.1655(4) 0.030 Uiso 1 1 calc R C4'A C -0.12135(11) 0.40040(8) 0.14936(5) 0.02479(13) Uani 1 1 d . C5'A C 0.05289(11) 0.49203(8) 0.19457(5) 0.02516(13) Uani 1 1 d . H5'A H 0.0964(6) 0.5731(11) 0.1618(4) 0.030 Uiso 1 1 calc R C6'A C 0.16345(10) 0.46562(7) 0.28733(5) 0.02229(12) Uani 1 1 d . H6'A H 0.2828(15) 0.5294(8) 0.3177(4) 0.027 Uiso 1 1 calc R C7'A C 0.22714(9) 0.32388(7) 0.43787(5) 0.01954(11) Uani 1 1 d . C8'A C 0.42210(10) 0.32064(8) 0.43216(5) 0.02412(13) Uani 1 1 d . H83A H 0.5002(7) 0.31891(8) 0.5039(6) 0.029 Uiso 1 1 calc R H84A H 0.4807(5) 0.4075(7) 0.4043(2) 0.029 Uiso 1 1 calc R C9'A C 0.42217(13) 0.19472(11) 0.36309(7) 0.03529(18) Uani 1 1 d . H94A H 0.5498(11) 0.2010(5) 0.3583(6) 0.053 Uiso 1 1 calc R H95A H 0.3413(13) 0.1934(6) 0.2935(6) 0.053 Uiso 1 1 calc R H96A H 0.3754(13) 0.1094(7) 0.3934(5) 0.053 Uiso 1 1 calc R O1B O -0.34584(11) 0.96623(7) -0.07092(5) 0.03587(14) Uani 1 1 d . C1B C -0.24319(13) 0.95866(9) 0.01587(7) 0.03018(15) Uani 1 1 d . H11A H -0.2234(3) 1.0322(10) 0.0701(8) 0.036 Uiso 1 1 calc R N1B N -0.15913(12) 0.85932(9) 0.04036(7) 0.03512(16) Uani 1 1 d . C2B C -0.1871(3) 0.74435(14) -0.03609(13) 0.0687(5) Uani 1 1 d . H21B H -0.2879(19) 0.7420(9) -0.0891(9) 0.103 Uiso 1 1 calc R H22B H -0.206(2) 0.6638(11) -0.0061(5) 0.103 Uiso 1 1 calc R H23B H -0.0846(16) 0.7554(8) -0.0608(9) 0.103 Uiso 1 1 calc R C3B C -0.04010(15) 0.86109(15) 0.14505(11) 0.0519(3) Uani 1 1 d . H31B H -0.0382(13) 0.9419(11) 0.1878(5) 0.078 Uiso 1 1 calc R H32B H 0.0857(14) 0.8646(13) 0.14099(14) 0.078 Uiso 1 1 calc R H33B H -0.0892(11) 0.7779(11) 0.1755(5) 0.078 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 0.0367(3) 0.0322(3) 0.0192(2) 0.00630(19) -0.0029(2) 0.0124(2) C1A 0.0208(2) 0.0205(2) 0.0151(2) 0.00281(18) 0.00317(19) 0.00624(19) C2A 0.0328(3) 0.0229(3) 0.0181(2) 0.0005(2) 0.0015(2) 0.0118(2) C3A 0.0318(3) 0.0236(3) 0.0209(3) 0.0031(2) 0.0017(2) 0.0124(2) C4A 0.0221(3) 0.0243(3) 0.0169(2) 0.0050(2) 0.0022(2) 0.0065(2) C5A 0.0261(3) 0.0224(3) 0.0156(2) 0.00147(19) 0.0024(2) 0.0063(2) C6A 0.0239(3) 0.0201(3) 0.0166(2) 0.00263(18) 0.0044(2) 0.0071(2) C7A 0.0210(2) 0.0204(2) 0.0153(2) 0.00286(18) 0.00282(19) 0.00649(19) C8A 0.0227(3) 0.0279(3) 0.0199(3) 0.0053(2) 0.0056(2) 0.0095(2) C9A 0.0253(3) 0.0409(4) 0.0374(4) 0.0151(3) 0.0084(3) 0.0046(3) O1'A 0.0481(4) 0.0340(3) 0.0239(3) 0.0046(2) -0.0091(2) 0.0169(3) C1'A 0.0205(2) 0.0234(3) 0.0147(2) 0.00285(18) 0.00319(19) 0.0067(2) C2'A 0.0224(3) 0.0255(3) 0.0185(2) 0.0033(2) 0.0016(2) 0.0048(2) C3'A 0.0237(3) 0.0277(3) 0.0198(3) 0.0010(2) -0.0004(2) 0.0075(2) C4'A 0.0308(3) 0.0271(3) 0.0169(2) 0.0015(2) 0.0002(2) 0.0143(2) C5'A 0.0318(3) 0.0247(3) 0.0195(3) 0.0053(2) 0.0045(2) 0.0101(2) C6'A 0.0239(3) 0.0238(3) 0.0185(2) 0.0036(2) 0.0043(2) 0.0059(2) C7'A 0.0198(2) 0.0224(3) 0.0156(2) 0.00246(18) 0.00267(19) 0.00564(19) C8'A 0.0202(3) 0.0326(3) 0.0195(3) 0.0038(2) 0.0040(2) 0.0078(2) C9'A 0.0333(4) 0.0478(5) 0.0285(4) -0.0029(3) 0.0079(3) 0.0184(4) O1B 0.0449(4) 0.0352(3) 0.0307(3) 0.0138(2) 0.0089(3) 0.0160(3) C1B 0.0360(4) 0.0294(3) 0.0306(3) 0.0102(3) 0.0117(3) 0.0145(3) N1B 0.0395(4) 0.0369(4) 0.0415(4) 0.0211(3) 0.0206(3) 0.0207(3) C2B 0.1200(14) 0.0431(6) 0.0738(9) 0.0211(6) 0.0531(10) 0.0480(8) C3B 0.0312(4) 0.0713(8) 0.0589(7) 0.0417(6) 0.0129(4) 0.0180(5) loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance O1A C4A 1.3692(8) O1A H1A 0.934(15) C1A C2A 1.3990(9) C1A C6A 1.4037(9) C1A C7A 1.4982(8) C2A C3A 1.3971(9) C2A H2A 1.0043 C3A C4A 1.3939(10) C3A H3A 0.9683 C4A C5A 1.3960(10) C5A C6A 1.3936(9) C5A H5A 0.9733 C6A H6A 0.9970 C7A C7'A 1.3539(9) C7A C8A 1.5177(10) C8A C9A 1.5293(11) C8A H81A 0.9920 C8A H82A 0.9920 C9A H91A 0.9850 C9A H92A 0.9850 C9A H93A 0.9850 O1'A C4'A 1.3712(8) O1'A H1'A 0.890(17) C1'A C2'A 1.4019(10) C1'A C6'A 1.4063(9) C1'A C7'A 1.4967(8) C2'A C3'A 1.3999(9) C2'A H2'A 0.9872 C3'A C4'A 1.3970(11) C3'A H3'A 0.9832 C4'A C5'A 1.3944(11) C5'A C6'A 1.3906(9) C5'A H5'A 0.9581 C6'A H6'A 0.9582 C7'A C8'A 1.5178(10) C8'A C9'A 1.5332(12) C8'A H83A 0.9999 C8'A H84A 0.9999 C9'A H94A 0.9791 C9'A H95A 0.9791 C9'A H96A 0.9791 O1B C1B 1.2457(10) C1B N1B 1.3178(11) C1B H11A 0.9705 N1B C2B 1.4476(17) N1B C3B 1.4650(14) C2B H21B 0.9045 C2B H22B 0.9045 C2B H23B 0.9045 C3B H31B 0.9677 C3B H32B 0.9677 C3B H33B 0.9677 loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle C4A O1A H1A 111.0(9) C2A C1A C6A 117.41(6) C2A C1A C7A 121.96(6) C6A C1A C7A 120.50(6) C3A C2A C1A 121.84(6) C3A C2A H2A 119.1 C1A C2A H2A 119.1 C4A C3A C2A 119.55(6) C4A C3A H3A 120.2 C2A C3A H3A 120.2 O1A C4A C3A 121.96(6) O1A C4A C5A 118.26(6) C3A C4A C5A 119.78(6) C6A C5A C4A 119.88(6) C6A C5A H5A 120.1 C4A C5A H5A 120.1 C5A C6A C1A 121.50(6) C5A C6A H6A 119.2 C1A C6A H6A 119.2 C7'A C7A C1A 122.56(6) C7'A C7A C8A 124.28(6) C1A C7A C8A 113.16(5) C7A C8A C9A 112.41(6) C7A C8A H81A 109.1 C9A C8A H81A 109.1 C7A C8A H82A 109.1 C9A C8A H82A 109.1 H81A C8A H82A 107.9 C8A C9A H91A 109.5 C8A C9A H92A 109.5 H91A C9A H92A 109.5 C8A C9A H93A 109.5 H91A C9A H93A 109.5 H92A C9A H93A 109.5 C4'A O1'A H1'A 110.9(11) C2'A C1'A C6'A 117.45(6) C2'A C1'A C7'A 122.72(6) C6'A C1'A C7'A 119.82(6) C3'A C2'A C1'A 121.50(6) C3'A C2'A H2'A 119.2 C1'A C2'A H2'A 119.3 C4'A C3'A C2'A 119.68(7) C4'A C3'A H3'A 120.2 C2'A C3'A H3'A 120.2 O1'A C4'A C5'A 117.76(7) O1'A C4'A C3'A 122.47(7) C5'A C4'A C3'A 119.76(6) C6'A C5'A C4'A 119.97(7) C6'A C5'A H5'A 120.0 C4'A C5'A H5'A 120.0 C5'A C6'A C1'A 121.62(6) C5'A C6'A H6'A 119.2 C1'A C6'A H6'A 119.2 C7A C7'A C1'A 122.34(6) C7A C7'A C8'A 123.33(6) C1'A C7'A C8'A 114.28(5) C7'A C8'A C9'A 112.82(6) C7'A C8'A H83A 109.0 C9'A C8'A H83A 109.0 C7'A C8'A H84A 109.0 C9'A C8'A H84A 109.0 H83A C8'A H84A 107.8 C8'A C9'A H94A 109.5 C8'A C9'A H95A 109.5 H94A C9'A H95A 109.5 C8'A C9'A H96A 109.5 H94A C9'A H96A 109.5 H95A C9'A H96A 109.5 O1B C1B N1B 125.62(9) O1B C1B H11A 117.2 N1B C1B H11A 117.2 C1B N1B C2B 119.98(10) C1B N1B C3B 121.10(10) C2B N1B C3B 118.90(10) N1B C2B H21B 109.5 N1B C2B H22B 109.5 H21B C2B H22B 109.5 N1B C2B H23B 109.5 H21B C2B H23B 109.5 H22B C2B H23B 109.5 N1B C3B H31B 109.5 N1B C3B H32B 109.5 H31B C3B H32B 109.5 N1B C3B H33B 109.5 H31B C3B H33B 109.5 H32B C3B H33B 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 0.69(11) C7A C1A C2A C3A -175.32(7) C1A C2A C3A C4A 0.06(12) C2A C3A C4A O1A 178.15(7) C2A C3A C4A C5A -1.44(11) O1A C4A C5A C6A -177.55(6) C3A C4A C5A C6A 2.06(11) C4A C5A C6A C1A -1.31(11) C2A C1A C6A C5A -0.06(10) C7A C1A C6A C5A 176.01(6) C2A C1A C7A C7'A -63.18(10) C6A C1A C7A C7'A 120.93(7) C2A C1A C7A C8A 117.43(7) C6A C1A C7A C8A -58.46(8) C7'A C7A C8A C9A 115.91(8) C1A C7A C8A C9A -64.71(8) C6'A C1'A C2'A C3'A -1.83(10) C7'A C1'A C2'A C3'A 178.78(6) C1'A C2'A C3'A C4'A 1.31(11) C2'A C3'A C4'A O1'A -179.26(7) C2'A C3'A C4'A C5'A -0.03(11) O1'A C4'A C5'A C6'A 178.61(7) C3'A C4'A C5'A C6'A -0.66(11) C4'A C5'A C6'A C1'A 0.09(11) C2'A C1'A C6'A C5'A 1.13(10) C7'A C1'A C6'A C5'A -179.47(6) C1A C7A C7'A C1'A 179.59(6) C8A C7A C7'A C1'A -1.09(10) C1A C7A C7'A C8'A -3.24(10) C8A C7A C7'A C8'A 176.07(6) C2'A C1'A C7'A C7A -59.21(10) C6'A C1'A C7'A C7A 121.42(8) C2'A C1'A C7'A C8'A 123.39(7) C6'A C1'A C7'A C8'A -55.98(8) C7A C7'A C8'A C9'A 115.42(8) C1'A C7'A C8'A C9'A -67.21(8) O1B C1B N1B C2B -1.79(16) O1B C1B N1B C3B 179.62(9) 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 0.934(15) 1.671(15) 2.6009(9) 173.6(14) y 1_646 O1'A H1'A O1A 0.890(17) 1.836(18) 2.7032(10) 164.2(16) y 1_454