#------------------------------------------------------------------------------ #$Date: 2016-02-13 14:50:18 +0200 (Sat, 13 Feb 2016) $ #$Revision: 176428 $ #$URL: file:///home/coder/svn-repositories/cod/cif/1/10/06/1100675.cif $ #------------------------------------------------------------------------------ # # This file is available in the Crystallography Open Database (COD), # http://www.crystallography.net/ # # All data on this site have been placed in the public domain by the # contributors. # data_1100675 loop_ _publ_author_name 'Doi, Mitsunobu' 'Ijiri, Yoshio' 'Akagi, Masao' 'Uenishi, Miharu' 'Urata, Hidehito' _publ_section_title ; Crystal Structure of 5'-Hydroxythalidomide In Vivo Metabolite of Thalidomide in Humans ; _journal_name_full ; Analytical Sciences: X-ray Structure Analysis Online ; _journal_page_first x51 _journal_page_last x52 _journal_paper_doi 10.2116/analscix.19.x51 _journal_volume 19 _journal_year 2003 _chemical_formula_moiety 'C13 H10 N2 O5' _chemical_formula_sum 'C13 H10 N2 O5' _chemical_formula_weight 274.23 _chemical_name_common 5hthalid _chemical_name_systematic 5'-Hydroxythalidomide _space_group_IT_number 15 _symmetry_cell_setting monoclinic _symmetry_space_group_name_Hall '-C 2yc' _symmetry_space_group_name_H-M 'C 1 2/c 1' _atom_sites_solution_hydrogens geom _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _cell_angle_alpha 90.00 _cell_angle_beta 95.9240(10) _cell_angle_gamma 90.00 _cell_formula_units_Z 8 _cell_length_a 21.7240(17) _cell_length_b 7.9633(6) _cell_length_c 13.6074(11) _cell_measurement_reflns_used 4272 _cell_measurement_temperature 90.0(2) _cell_measurement_theta_max 28.0 _cell_measurement_theta_min 2.7 _cell_volume 2341.4(3) _diffrn_ambient_temperature 90.0(2) _diffrn_detector_area_resol_mean 8.366 _diffrn_measurement_device_type 'Bruker AXS, SMART APEX area detector' _diffrn_measurement_method \w-scan _diffrn_radiation_monochromator graphite _diffrn_radiation_source 'MacScience, M18XCE rotating anode' _diffrn_radiation_type MoK\a _diffrn_radiation_wavelength 0.71073 _diffrn_reflns_av_R_equivalents 0.0234 _diffrn_reflns_av_sigmaI/netI 0.0226 _diffrn_reflns_limit_h_max 27 _diffrn_reflns_limit_h_min -28 _diffrn_reflns_limit_k_max 10 _diffrn_reflns_limit_k_min -10 _diffrn_reflns_limit_l_max 18 _diffrn_reflns_limit_l_min -17 _diffrn_reflns_number 9927 _diffrn_reflns_theta_max 28.28 _diffrn_reflns_theta_min 2.73 _diffrn_standards_decay_% 0.08 _diffrn_standards_interval_count 9927 _diffrn_standards_interval_time 360 _diffrn_standards_number 135 _exptl_absorpt_coefficient_mu 0.122 _exptl_absorpt_correction_T_max 1.0 _exptl_absorpt_correction_T_min 0.8821 _exptl_absorpt_correction_type empirical _exptl_absorpt_process_details 'SADABS (Sheldrick, 1996)' _exptl_crystal_colour colourless _exptl_crystal_density_diffrn 1.556 _exptl_crystal_density_method 'not measured' _exptl_crystal_description plate _exptl_crystal_F_000 1136 _exptl_crystal_size_max 0.38 _exptl_crystal_size_mid 0.30 _exptl_crystal_size_min 0.10 _refine_ls_extinction_method none _refine_ls_goodness_of_fit_ref 1.248 _refine_ls_hydrogen_treatment mixed _refine_ls_matrix_type full _refine_ls_number_parameters 185 _refine_ls_number_reflns 2770 _refine_ls_number_restraints 0 _refine_ls_restrained_S_all 1.248 _refine_ls_R_factor_all 0.0662 _refine_ls_R_factor_gt 0.0639 _refine_ls_shift/su_max <0.001 _refine_ls_shift/su_mean 0.000 _refine_ls_structure_factor_coef Fsqd _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0478P)^2^+5.7973P] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_gt 0.1432 _refine_ls_wR_factor_ref 0.1445 _reflns_number_gt 2661 _reflns_number_total 2770 _reflns_threshold_expression I>2\s(I) _cod_original_sg_symbol_H-M C2/c _cod_database_code 1100675 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' 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 C1 C 0.02939(10) 0.6082(2) 0.63039(14) 0.0153(4) Uani 1 1 d . . . O1 O 0.01652(7) 0.46223(19) 0.61661(12) 0.0213(4) Uani 1 1 d . . . N2 N 0.08850(8) 0.6692(2) 0.66432(13) 0.0150(4) Uani 1 1 d . . . C3 C 0.09019(10) 0.8447(3) 0.66399(14) 0.0151(4) Uani 1 1 d . . . O3 O 0.13670(7) 0.92752(19) 0.68384(12) 0.0213(4) Uani 1 1 d . . . C3A C 0.02551(9) 0.9003(3) 0.63583(14) 0.0141(4) Uani 1 1 d . . . C4 C 0.00125(10) 1.0609(3) 0.62712(15) 0.0171(4) Uani 1 1 d . . . H1 H 0.0266 1.1572 0.6400 0.021 Uiso 1 1 calc R . . C5 C -0.06220(11) 1.0753(3) 0.59859(16) 0.0206(5) Uani 1 1 d . . . H2 H -0.0805 1.1835 0.5916 0.025 Uiso 1 1 calc R . . C6 C -0.09901(11) 0.9330(3) 0.58023(16) 0.0224(5) Uani 1 1 d . . . H3 H -0.1421 0.9462 0.5615 0.027 Uiso 1 1 calc R . . C7 C -0.07405(10) 0.7719(3) 0.58881(15) 0.0188(4) Uani 1 1 d . . . H4 H -0.0991 0.6749 0.5761 0.023 Uiso 1 1 calc R . . C7A C -0.01107(10) 0.7595(2) 0.61679(14) 0.0145(4) Uani 1 1 d . . . N1' N 0.20422(8) 0.3992(2) 0.56697(12) 0.0151(4) Uani 1 1 d . . . H5 H 0.2181 0.3819 0.5093 0.018 Uiso 1 1 calc R . . C2' C 0.16300(9) 0.5297(3) 0.57195(15) 0.0156(4) Uani 1 1 d . . . O2' O 0.14389(8) 0.6066(2) 0.49844(11) 0.0225(4) Uani 1 1 d . . . C3' C 0.14497(9) 0.5700(3) 0.67457(14) 0.0138(4) Uani 1 1 d . . . H6 H 0.1784 0.6430 0.7077 0.017 Uiso 1 1 calc R . . C4' C 0.14231(9) 0.4122(3) 0.73765(14) 0.0154(4) Uani 1 1 d . . . H7 H 0.1323 0.4429 0.8047 0.018 Uiso 1 1 calc R . . H8 H 0.1095 0.3361 0.7076 0.018 Uiso 1 1 calc R . . C5' C 0.20469(9) 0.3238(3) 0.74428(14) 0.0141(4) Uani 1 1 d . . . H9 H 0.2355 0.4013 0.7801 0.017 Uiso 1 1 calc R . . O5' O 0.20621(7) 0.17306(19) 0.79890(11) 0.0175(3) Uani 1 1 d . . . H10 H 0.1799(13) 0.101(4) 0.765(2) 0.025(7) Uiso 1 1 d . . . C6' C 0.22604(9) 0.2929(3) 0.64228(15) 0.0142(4) Uani 1 1 d . . . O6' O 0.26113(7) 0.1789(2) 0.62674(11) 0.0225(4) 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 C1 0.0228(10) 0.0115(9) 0.0118(9) 0.0002(7) 0.0030(7) 0.0018(8) O1 0.0234(8) 0.0115(7) 0.0275(8) -0.0004(6) -0.0039(6) -0.0004(6) N2 0.0186(9) 0.0111(8) 0.0157(8) 0.0004(6) 0.0033(6) 0.0036(6) C3 0.0216(10) 0.0128(9) 0.0114(9) -0.0013(7) 0.0052(7) 0.0019(8) O3 0.0213(8) 0.0171(7) 0.0254(8) -0.0024(6) 0.0018(6) -0.0029(6) C3A 0.0189(10) 0.0133(9) 0.0112(8) 0.0000(7) 0.0057(7) 0.0022(7) C4 0.0263(11) 0.0120(9) 0.0137(9) 0.0001(7) 0.0051(8) 0.0036(8) C5 0.0289(11) 0.0168(10) 0.0172(10) 0.0038(8) 0.0083(8) 0.0091(9) C6 0.0199(10) 0.0304(12) 0.0177(10) 0.0043(9) 0.0054(8) 0.0077(9) C7 0.0211(11) 0.0199(10) 0.0159(10) 0.0028(8) 0.0035(8) -0.0022(8) C7A 0.0206(10) 0.0115(9) 0.0122(9) 0.0006(7) 0.0053(7) 0.0020(8) N1' 0.0202(9) 0.0156(8) 0.0100(7) 0.0015(6) 0.0040(6) 0.0053(7) C2' 0.0171(10) 0.0134(9) 0.0163(9) -0.0002(8) 0.0021(7) 0.0015(7) O2' 0.0299(9) 0.0228(8) 0.0151(7) 0.0058(6) 0.0040(6) 0.0116(7) C3' 0.0139(9) 0.0135(9) 0.0139(9) -0.0016(7) 0.0006(7) 0.0012(7) C4' 0.0160(9) 0.0176(10) 0.0128(9) 0.0007(8) 0.0027(7) 0.0018(8) C5' 0.0180(9) 0.0134(9) 0.0111(9) 0.0007(7) 0.0024(7) 0.0013(7) O5' 0.0212(8) 0.0151(7) 0.0162(7) 0.0039(6) 0.0016(6) 0.0018(6) C6' 0.0133(9) 0.0141(9) 0.0150(9) 0.0014(7) 0.0013(7) 0.0007(7) O6' 0.0261(8) 0.0254(8) 0.0167(7) 0.0054(6) 0.0059(6) 0.0140(7) 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'