#------------------------------------------------------------------------------ #$Date: 2017-04-28 08:07:40 +0300 (Fri, 28 Apr 2017) $ #$Revision: 195842 $ #$URL: file:///home/coder/svn-repositories/cod/cif/7/22/81/7228138.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_7228138 loop_ _publ_author_name 'Xiong, Xinnuo' 'Du, Qiaohong' 'Zeng, Xia' 'He, Jiawei' 'Yang, Hongqin' 'Li, Hui' _publ_section_title ; Solvates and polymorphs of rebamipide: preparation, characterization, and physicochemical analysis ; _journal_issue 38 _journal_name_full 'RSC Adv.' _journal_page_first 23279 _journal_paper_doi 10.1039/C7RA02895D _journal_volume 7 _journal_year 2017 _chemical_formula_moiety 'C19 H15 Cl N2 O4, C H2 Cl2' _chemical_formula_sum 'C20 H17 Cl3 N2 O4' _chemical_formula_weight 455.71 _chemical_name_systematic ; ? ; _space_group_crystal_system monoclinic _space_group_IT_number 14 _space_group_name_Hall '-P 2ybc' _space_group_name_H-M_alt 'P 1 21/c 1' _symmetry_space_group_name_Hall '-P 2ybc' _symmetry_space_group_name_H-M 'P 1 21/c 1' _atom_sites_solution_hydrogens geom _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _audit_creation_date 2016-03-22 _audit_creation_method ; Olex2 1.2 (compiled 2016.02.19 svn.r3266 for OlexSys, GUI svn.r5155) ; _audit_update_record ; 2016-08-22 deposited with the CCDC. 2017-04-21 downloaded from the CCDC. ; _cell_angle_alpha 90.00 _cell_angle_beta 136.08(2) _cell_angle_gamma 90.00 _cell_formula_units_Z 4 _cell_length_a 14.3285(16) _cell_length_b 9.7542(4) _cell_length_c 21.475(2) _cell_measurement_reflns_used 2179 _cell_measurement_temperature 142.95(10) _cell_measurement_theta_max 27.4520 _cell_measurement_theta_min 3.4340 _cell_volume 2081.9(8) _computing_cell_refinement 'CrysAlisPro 1.171.38.41 (Rigaku OD, 2015)' _computing_data_collection 'CrysAlisPro 1.171.38.41 (Rigaku OD, 2015)' _computing_data_reduction 'CrysAlisPro 1.171.38.41 (Rigaku OD, 2015)' _computing_molecular_graphics 'Olex2 (Dolomanov et al., 2009)' _computing_publication_material 'Olex2 (Dolomanov et al., 2009)' _computing_structure_refinement 'ShelXL (Sheldrick, 2015)' _computing_structure_solution 'ShelXS (Sheldrick, 2008)' _diffrn_ambient_environment N~2~ _diffrn_ambient_temperature 142.95(10) _diffrn_detector 'CCD plate' _diffrn_detector_area_resol_mean 16.0874 _diffrn_detector_type Eos _diffrn_measured_fraction_theta_full 0.998 _diffrn_measured_fraction_theta_max 0.998 _diffrn_measurement_details ; List of Runs (angles in degrees, time in seconds): # Type Start End Width t~exp~ \w \q \k \f Frames #-------------------------------------------------------------------------- 1 \w -21.00 10.00 1.00 7.50 -- -14.97 -99.00-150.00 31 2 \w -47.00 45.00 1.00 7.50 -- 16.69 -19.00 30.00 92 3 \w -52.00 32.00 1.00 7.50 -- 16.69 -19.00 -60.00 84 ; _diffrn_measurement_device 'four-circle diffractometer' _diffrn_measurement_device_type 'Xcalibur, Eos' _diffrn_measurement_method '\w scans' _diffrn_orient_matrix_type 'CrysAlisPro convention (1999,Acta A55,543-557)' _diffrn_orient_matrix_UB_11 -0.0407074000 _diffrn_orient_matrix_UB_12 -0.0112349000 _diffrn_orient_matrix_UB_13 0.0070693000 _diffrn_orient_matrix_UB_21 0.0428028000 _diffrn_orient_matrix_UB_22 -0.0545278000 _diffrn_orient_matrix_UB_23 0.0298331000 _diffrn_orient_matrix_UB_31 0.0400471000 _diffrn_orient_matrix_UB_32 0.0467860000 _diffrn_orient_matrix_UB_33 0.0364481000 _diffrn_radiation_monochromator graphite _diffrn_radiation_probe x-ray _diffrn_radiation_type MoK\a _diffrn_radiation_wavelength 0.71073 _diffrn_reflns_av_R_equivalents 0.0000 _diffrn_reflns_av_unetI/netI 0.0508 _diffrn_reflns_limit_h_max 12 _diffrn_reflns_limit_h_min -17 _diffrn_reflns_limit_k_max 11 _diffrn_reflns_limit_k_min -12 _diffrn_reflns_limit_l_max 26 _diffrn_reflns_limit_l_min -18 _diffrn_reflns_number 8491 _diffrn_reflns_theta_full 26.37 _diffrn_reflns_theta_max 26.37 _diffrn_reflns_theta_min 2.93 _diffrn_source 'fine-focus sealed X-ray tube' _diffrn_source_type 'Enhance (Mo) X-ray Source' _exptl_absorpt_coefficient_mu 0.470 _exptl_absorpt_correction_T_max 1.00000 _exptl_absorpt_correction_T_min 0.94036 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details ; CrysAlisPro 1.171.38.41 (Rigaku Oxford Diffraction, 2015) Empirical absorption correction using spherical harmonics, implemented in SCALE3 ABSPACK scaling algorithm. ; _exptl_crystal_colour colorless _exptl_crystal_density_diffrn 1.454 _exptl_crystal_density_method 'not measured' _exptl_crystal_description block _exptl_crystal_F_000 936 _exptl_crystal_size_max 0.4 _exptl_crystal_size_mid 0.35 _exptl_crystal_size_min 0.3 _refine_diff_density_max 0.525 _refine_diff_density_min -0.627 _refine_diff_density_rms 0.063 _refine_ls_extinction_method none _refine_ls_goodness_of_fit_ref 0.912 _refine_ls_hydrogen_treatment mixed _refine_ls_matrix_type full _refine_ls_number_parameters 271 _refine_ls_number_reflns 8491 _refine_ls_number_restraints 0 _refine_ls_restrained_S_all 0.912 _refine_ls_R_factor_all 0.1030 _refine_ls_R_factor_gt 0.0590 _refine_ls_shift/su_max 0.003 _refine_ls_shift/su_mean 0.000 _refine_ls_structure_factor_coef Fsqd _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.1059P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_gt 0.1612 _refine_ls_wR_factor_ref 0.1755 _reflns_number_gt 4598 _reflns_number_total 8491 _reflns_threshold_expression >2sigma(I) _cod_data_source_file c7ra02895d2.cif _cod_data_source_block twin_twin1_hklf4 _cod_original_cell_volume 2081.9(3) _cod_database_code 7228138 _chemical_oxdiff_formula c8h4o4n2 _olex2_refinement_description ; 1. Twinned data refinement Scales: 0.5891(10) 0.4109(10) 2. Fixed Uiso At 1.2 times of: All C(H) groups, All C(H,H) groups, All N(H) groups 3.a Ternary CH refined with riding coordinates: C11(H11) 3.b Secondary CH2 refined with riding coordinates: C10(H10A,H10B), C20(H20A,H20B) 3.c Aromatic/amide H refined with riding coordinates: N2(H2), C2(H2A), C5(H5), C6(H6), C7(H7), C8(H8), C15(H15), C16(H16), C18(H18), C19(H19) ; _olex2_submission_special_instructions 'No special instructions were received' _oxdiff_exptl_absorpt_empirical_details ; Empirical correction (ABSPACK) includes: - Absorption correction using spherical harmonics - Frame scaling ; _oxdiff_exptl_absorpt_empirical_full_max 1.084 _oxdiff_exptl_absorpt_empirical_full_min 0.853 _oxdiff_twin_integration_method simultaneous _oxdiff_twin_items 2 _twin_special_details ; Component 2 rotated by 4.0599\% around [0.44 0.06 -0.90] (reciprocal) or [0.03 0.30 -0.95] (direct) ; loop_ _space_group_symop_id _space_group_symop_operation_xyz 1 'x, y, z' 2 '-x, y+1/2, -z+1/2' 3 '-x, -y, -z' 4 'x, -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_calc_flag _atom_site_refinement_flags_posn Cl1 Cl 0.44575(8) 0.27972(12) 0.39439(5) 0.1107(4) Uani 1 d . O1 O 0.60502(13) 0.63500(12) 0.82879(9) 0.0434(4) Uani 1 d . O2 O 0.85501(15) 0.03512(18) 0.81047(10) 0.0607(5) Uani 1 d . O3 O 0.85392(14) -0.12788(13) 0.96695(9) 0.0510(5) Uani 1 d . O4 O 0.65480(14) -0.12048(15) 0.82547(9) 0.0564(5) Uani 1 d . H4 H 0.643(2) -0.209(3) 0.8320(16) 0.071(8) Uiso 1 d . N1 N 0.81476(16) 0.58810(17) 0.96497(10) 0.0332(4) Uani 1 d . H1 H 0.830(2) 0.677(2) 0.9700(15) 0.058(7) Uiso 1 d . N2 N 0.70155(16) 0.12935(14) 0.80026(10) 0.0316(4) Uani 1 d . H2 H 0.6262 0.1759 0.7681 0.038 Uiso 1 calc R C1 C 0.69146(19) 0.54824(19) 0.88822(13) 0.0323(5) Uani 1 d . C2 C 0.66408(18) 0.40460(18) 0.87774(12) 0.0331(5) Uani 1 d . H2A H 0.5764 0.3732 0.8252 0.040 Uiso 1 calc R C3 C 0.75819(19) 0.31182(18) 0.93973(12) 0.0294(5) Uani 1 d . C4 C 0.89068(19) 0.35918(18) 1.02052(12) 0.0305(5) Uani 1 d . C5 C 0.9973(2) 0.2720(2) 1.09025(13) 0.0403(5) Uani 1 d . H5 H 0.9832 0.1757 1.0848 0.048 Uiso 1 calc R C6 C 1.1192(2) 0.3236(2) 1.16468(13) 0.0474(6) Uani 1 d . H6 H 1.1893 0.2633 1.2108 0.057 Uiso 1 calc R C7 C 1.1423(2) 0.4644(2) 1.17399(14) 0.0487(6) Uani 1 d . H7 H 1.2283 0.4993 1.2264 0.058 Uiso 1 calc R C8 C 1.0425(2) 0.5529(2) 1.10845(13) 0.0398(5) Uani 1 d . H8 H 1.0585 0.6489 1.1149 0.048 Uiso 1 calc R C9 C 0.91641(18) 0.49979(18) 1.03180(12) 0.0304(5) Uani 1 d . C10 C 0.7247(2) 0.16174(17) 0.92375(13) 0.0329(5) Uani 1 d . H10A H 0.6258 0.1509 0.8787 0.040 Uiso 1 calc R H10B H 0.7642 0.1189 0.9803 0.040 Uiso 1 calc R C11 C 0.77646(19) 0.08637(18) 0.89081(12) 0.0304(5) Uani 1 d . H11 H 0.8733 0.1105 0.9312 0.036 Uiso 1 calc R C12 C 0.7664(2) -0.06610(19) 0.89829(13) 0.0333(5) Uani 1 d . C13 C 0.7485(2) 0.0973(2) 0.76627(13) 0.0372(5) Uani 1 d . C14 C 0.6685(2) 0.1438(2) 0.67271(13) 0.0414(5) Uani 1 d . C15 C 0.5765(2) 0.2506(2) 0.63177(15) 0.0512(6) Uani 1 d . H15 H 0.5601 0.2948 0.6626 0.061 Uiso 1 calc R C16 C 0.5086(2) 0.2931(3) 0.54632(16) 0.0664(8) Uani 1 d . H16 H 0.4462 0.3667 0.5183 0.080 Uiso 1 calc R C17 C 0.5329(2) 0.2268(3) 0.50266(16) 0.0698(8) Uani 1 d . C18 C 0.6221(3) 0.1214(3) 0.54122(17) 0.0716(8) Uani 1 d . H18 H 0.6368 0.0766 0.5096 0.086 Uiso 1 calc R C19 C 0.6907(2) 0.0807(3) 0.62664(15) 0.0595(7) Uani 1 d . H19 H 0.7542 0.0082 0.6544 0.071 Uiso 1 calc R Cl2 Cl 0.18809(11) 0.53831(11) 0.36461(7) 0.1180(4) Uani 1 d . Cl3 Cl 0.14339(14) 0.24972(12) 0.36263(10) 0.1493(5) Uani 1 d . C20 C 0.0738(3) 0.4104(5) 0.3127(3) 0.1268(14) Uani 1 d . H20A H 0.0264 0.4055 0.2494 0.152 Uiso 1 calc R H20B H 0.0062 0.4326 0.3126 0.152 Uiso 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 Cl1 0.0586(5) 0.2188(11) 0.0454(4) 0.0395(5) 0.0343(4) 0.0083(6) O1 0.0319(8) 0.0251(7) 0.0444(8) 0.0052(6) 0.0178(7) 0.0015(6) O2 0.0460(10) 0.0930(13) 0.0461(9) 0.0188(9) 0.0341(8) 0.0277(9) O3 0.0489(9) 0.0260(7) 0.0344(8) 0.0047(6) 0.0154(8) -0.0007(7) O4 0.0377(9) 0.0265(8) 0.0445(9) 0.0061(7) 0.0094(8) -0.0042(7) N1 0.0342(10) 0.0197(9) 0.0340(9) -0.0017(8) 0.0206(8) -0.0008(8) N2 0.0311(9) 0.0256(8) 0.0327(9) 0.0062(7) 0.0213(8) 0.0079(7) C1 0.0295(11) 0.0266(11) 0.0339(10) -0.0009(9) 0.0206(10) 0.0002(9) C2 0.0286(11) 0.0277(11) 0.0326(10) -0.0035(9) 0.0187(9) -0.0036(9) C3 0.0382(11) 0.0258(10) 0.0309(10) 0.0002(8) 0.0271(10) 0.0002(9) C4 0.0360(11) 0.0270(10) 0.0294(10) 0.0029(8) 0.0238(9) 0.0050(9) C5 0.0463(13) 0.0338(11) 0.0346(11) 0.0055(9) 0.0271(11) 0.0080(10) C6 0.0393(13) 0.0519(14) 0.0306(11) 0.0093(10) 0.0184(11) 0.0151(11) C7 0.0353(13) 0.0583(15) 0.0323(11) -0.0074(11) 0.0176(10) -0.0033(11) C8 0.0378(12) 0.0346(11) 0.0358(11) -0.0050(9) 0.0228(10) -0.0024(10) C9 0.0310(11) 0.0296(11) 0.0284(10) 0.0013(8) 0.0206(9) 0.0035(9) C10 0.0412(12) 0.0229(10) 0.0386(11) 0.0035(9) 0.0300(10) 0.0016(9) C11 0.0305(10) 0.0227(10) 0.0318(10) 0.0015(8) 0.0204(9) 0.0005(8) C12 0.0322(11) 0.0253(11) 0.0310(11) -0.0002(9) 0.0190(10) 0.0024(9) C13 0.0350(12) 0.0344(11) 0.0381(11) 0.0010(10) 0.0250(11) 0.0014(10) C14 0.0343(12) 0.0496(13) 0.0348(11) 0.0020(10) 0.0231(10) -0.0031(10) C15 0.0481(14) 0.0614(15) 0.0434(13) 0.0100(12) 0.0327(12) 0.0052(12) C16 0.0504(15) 0.087(2) 0.0498(15) 0.0281(14) 0.0320(14) 0.0128(14) C17 0.0392(15) 0.124(3) 0.0369(13) 0.0146(15) 0.0243(13) -0.0075(16) C18 0.0543(16) 0.120(2) 0.0453(14) -0.0018(16) 0.0375(14) -0.0001(17) C19 0.0490(15) 0.0819(18) 0.0470(14) 0.0029(13) 0.0344(13) 0.0085(13) Cl2 0.1289(8) 0.1280(8) 0.1154(7) -0.0218(6) 0.0941(7) -0.0165(6) Cl3 0.1589(11) 0.1372(10) 0.1984(13) -0.0090(8) 0.1443(11) -0.0220(8) C20 0.072(2) 0.197(4) 0.125(3) -0.006(3) 0.075(2) 0.010(3) 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' 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' loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle C12 O4 H4 114.1(15) C1 N1 H1 115.2(14) C1 N1 C9 124.47(17) C9 N1 H1 120.2(15) C11 N2 H2 120.4 C13 N2 H2 120.4 C13 N2 C11 119.13(16) O1 C1 N1 120.80(17) O1 C1 C2 122.60(17) N1 C1 C2 116.60(17) C1 C2 H2A 118.8 C3 C2 C1 122.42(17) C3 C2 H2A 118.8 C2 C3 C4 119.04(17) C2 C3 C10 120.02(17) C4 C3 C10 120.94(16) C5 C4 C3 124.23(17) C9 C4 C3 118.53(16) C9 C4 C5 117.25(17) C4 C5 H5 119.4 C6 C5 C4 121.13(19) C6 C5 H5 119.4 C5 C6 H6 119.8 C5 C6 C7 120.43(19) C7 C6 H6 119.8 C6 C7 H7 119.7 C8 C7 C6 120.66(19) C8 C7 H7 119.7 C7 C8 H8 120.5 C7 C8 C9 118.92(19) C9 C8 H8 120.5 N1 C9 C4 118.89(17) N1 C9 C8 119.50(17) C4 C9 C8 121.60(17) C3 C10 H10A 109.0 C3 C10 H10B 109.0 C3 C10 C11 113.05(16) H10A C10 H10B 107.8 C11 C10 H10A 109.0 C11 C10 H10B 109.0 N2 C11 C10 110.10(15) N2 C11 H11 108.6 N2 C11 C12 113.03(15) C10 C11 H11 108.6 C12 C11 C10 107.92(16) C12 C11 H11 108.6 O3 C12 O4 124.37(18) O3 C12 C11 121.84(17) O4 C12 C11 113.76(16) O2 C13 N2 121.74(19) O2 C13 C14 120.7(2) N2 C13 C14 117.49(19) C15 C14 C13 122.5(2) C19 C14 C13 118.5(2) C19 C14 C15 118.9(2) C14 C15 H15 119.8 C16 C15 C14 120.3(2) C16 C15 H15 119.8 C15 C16 H16 120.6 C17 C16 C15 118.9(3) C17 C16 H16 120.6 C16 C17 Cl1 118.7(2) C18 C17 Cl1 119.4(2) C18 C17 C16 121.9(2) C17 C18 H18 120.5 C17 C18 C19 119.0(3) C19 C18 H18 120.5 C14 C19 H19 119.5 C18 C19 C14 121.0(3) C18 C19 H19 119.5 Cl2 C20 Cl3 113.8(2) Cl2 C20 H20A 108.8 Cl2 C20 H20B 108.8 Cl3 C20 H20A 108.8 Cl3 C20 H20B 108.8 H20A C20 H20B 107.7 loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance Cl1 C17 1.746(3) O1 C1 1.266(2) O2 C13 1.229(2) O3 C12 1.203(2) O4 H4 0.91(3) O4 C12 1.297(2) N1 H1 0.89(2) N1 C1 1.339(2) N1 C9 1.383(2) N2 H2 0.8800 N2 C11 1.450(2) N2 C13 1.339(3) C1 C2 1.428(3) C2 H2A 0.9500 C2 C3 1.350(2) C3 C4 1.443(3) C3 C10 1.501(3) C4 C5 1.415(3) C4 C9 1.395(2) C5 H5 0.9500 C5 C6 1.355(3) C6 H6 0.9500 C6 C7 1.393(3) C7 H7 0.9500 C7 C8 1.369(3) C8 H8 0.9500 C8 C9 1.399(3) C10 H10A 0.9900 C10 H10B 0.9900 C10 C11 1.533(3) C11 H11 1.0000 C11 C12 1.514(3) C13 C14 1.496(3) C14 C15 1.388(3) C14 C19 1.383(3) C15 H15 0.9500 C15 C16 1.383(3) C16 H16 0.9500 C16 C17 1.374(4) C17 C18 1.361(4) C18 H18 0.9500 C18 C19 1.375(3) C19 H19 0.9500 Cl2 C20 1.689(4) Cl3 C20 1.749(4) C20 H20A 0.9900 C20 H20B 0.9900 loop_ _twin_individual_id _twin_individual_mass_fraction_refined _oxdiff_twin_reflns_isolated _oxdiff_twin_reflns_overlapped _twin_individual_twin_lattice_type _twin_individual_twin_matrix_11 _twin_individual_twin_matrix_12 _twin_individual_twin_matrix_13 _twin_individual_twin_matrix_21 _twin_individual_twin_matrix_22 _twin_individual_twin_matrix_23 _twin_individual_twin_matrix_31 _twin_individual_twin_matrix_32 _twin_individual_twin_matrix_33 1 0.5891(10) 7828 1794 ref 1.0000 0.0000 0.0000 0.0000 1.0000 0.0000 0.0000 0.0000 1.0000 2 0.4109(10) 7858 1794 nmt 1.0070 0.0709 0.0087 -0.0688 0.9964 -0.0336 -0.0214 0.0016 0.9876