#------------------------------------------------------------------------------
#$Date: 2025-08-22 17:52:37 +0200 (Fri 22 de Aug de 2025) $
#$Revision: 301865 $
#$URL: svn://www.crystallography.net/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
_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  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -21.00  10.00   1.00    7.50    --  -14.97 -99.00-150.00   31
  2  ω    -47.00  45.00   1.00    7.50    --   16.69 -19.00  30.00   92
  3  ω    -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       'ω 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/[σ²(Fo²)+(0.1059P)²+0.0000P] where P=(Fo²+2Fc²)/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)
_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)
;
_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
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_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
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 PubChem 139203451
