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#$Date: 2023-10-10 05:19:25 +0300 (Tue, 10 Oct 2023) $
#$Revision: 286864 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/02/28/2022898.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_2022898
loop_
_publ_author_name
'Rajendrakumar, Satyasree'
'Surampudi Venkata Sai Durga, Anuja'
'Balasubramanian, Sridhar'
_publ_section_title
;
 Strategic synthon approach in obtaining cocrystals and cocrystal
 polymorphs of a high-Z′ system deferiprone -- an anti-thalassemia
 drug
;
_journal_coeditor_code           LO5093
_journal_issue                   6
_journal_name_full
'Acta Crystallographica Section B Structural Science, Crystal Engineering and Materials'
_journal_page_first              946
_journal_page_last               964
_journal_paper_doi               10.1107/S205252062100980X
_journal_volume                  77
_journal_year                    2021
_chemical_formula_moiety         'C7 H9 N O2, 2(C6 H6 O3)'
_chemical_formula_sum            'C19 H21 N O8'
_chemical_formula_weight         391.37
_chemical_name_common            'Deferiprone-bis(Pyrogallol) (1:2)'
_space_group_crystal_system      monoclinic
_space_group_IT_number           15
_space_group_name_Hall           '-C 2yc'
_space_group_name_H-M_alt        'C 1 2/c 1'
_atom_sites_solution_hydrogens   mixed
_audit_creation_method           SHELXL-2018/3
_cell_angle_alpha                90
_cell_angle_beta                 107.0808(5)
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   28.0626(4)
_cell_length_b                   9.27190(10)
_cell_length_c                   14.6075(2)
_cell_measurement_reflns_used    9898
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      30.57
_cell_measurement_theta_min      2.62
_cell_volume                     3633.13(8)
_computing_cell_refinement       'SAINT (Bruker, 2016)'
_computing_data_collection       'APEX3 (Bruker, 2016)'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'DIAMOND (Brandenburg & Putz, 2005)'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_structure_solution    'SHELXT (Sheldrick, 2015)'
_diffrn_ambient_temperature      100(2)
_diffrn_measured_fraction_theta_full 0.995
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measurement_device_type  'Bruker D8 QUEST PHOTON-100'
_diffrn_measurement_method       'ω and φ'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0271
_diffrn_reflns_av_unetI/netI     0.0198
_diffrn_reflns_Laue_measured_fraction_full 0.995
_diffrn_reflns_Laue_measured_fraction_max 0.996
_diffrn_reflns_limit_h_max       34
_diffrn_reflns_limit_h_min       -34
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            23872
_diffrn_reflns_point_group_measured_fraction_full 0.995
_diffrn_reflns_point_group_measured_fraction_max 0.996
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         26.249
_diffrn_reflns_theta_min         2.324
_diffrn_source                   microfocus
_exptl_absorpt_coefficient_mu    0.113
_exptl_absorpt_correction_T_max  0.7461
_exptl_absorpt_correction_T_min  0.6926
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS, Bruker, 2016'
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.431
_exptl_crystal_description       needle
_exptl_crystal_F_000             1648
_exptl_crystal_size_max          0.320
_exptl_crystal_size_mid          0.180
_exptl_crystal_size_min          0.160
_refine_diff_density_max         0.434
_refine_diff_density_min         -0.304
_refine_diff_density_rms         0.072
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.046
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     283
_refine_ls_number_reflns         3664
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.046
_refine_ls_R_factor_all          0.0379
_refine_ls_R_factor_gt           0.0350
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.0563P)²+2.7534P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0936
_refine_ls_wR_factor_ref         0.0967
_reflns_Friedel_coverage         0.000
_reflns_number_gt                3357
_reflns_number_total             3664
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            lo5093sup1.cif
_cod_data_source_block           KA803_0m_def-pyro_1_2
_cod_original_sg_symbol_H-M      'C 2/c'
_cod_database_code               2022898
_shelx_shelxl_version_number     2018/3
_shelx_space_group_comment
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_shelx_estimated_absorpt_t_min   0.965
_shelx_estimated_absorpt_t_max   0.982
loop_
_space_group_symop_operation_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_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C 0.43916(4) -0.07673(12) 1.02071(8) 0.0132(2) Uani 1 1 d . . . . .
C2 C 0.44400(4) 0.07094(12) 1.02368(7) 0.0117(2) Uani 1 1 d . . . . .
C3 C 0.44137(4) 0.15283(12) 0.93988(7) 0.0113(2) Uani 1 1 d . . . . .
C4 C 0.43261(4) 0.07434(13) 0.85397(8) 0.0145(2) Uani 1 1 d . . . . .
H4 H 0.429760 0.123952 0.795703 0.017 Uiso 1 1 calc R U . . .
C5 C 0.42819(4) -0.07221(13) 0.85358(8) 0.0158(2) Uani 1 1 d . . . . .
H5 H 0.422651 -0.123025 0.794902 0.019 Uiso 1 1 calc R U . . .
C6 C 0.42792(4) -0.30550(13) 0.93044(9) 0.0205(3) Uani 1 1 d . . . . .
H6A H 0.418201 -0.336831 0.863421 0.031 Uiso 1 1 calc R U . . .
H6B H 0.402856 -0.337643 0.960631 0.031 Uiso 1 1 calc R U . . .
H6C H 0.460343 -0.347465 0.964452 0.031 Uiso 1 1 calc R U . . .
C7 C 0.44205(5) -0.16221(13) 1.10874(9) 0.0193(2) Uani 1 1 d . . . . .
H7A H 0.453893 -0.100239 1.165233 0.029 Uiso 1 1 calc R U . . .
H7B H 0.465237 -0.242826 1.113520 0.029 Uiso 1 1 calc R U . . .
H7C H 0.408913 -0.199693 1.105288 0.029 Uiso 1 1 calc R U . . .
O1 O 0.45241(3) 0.13873(9) 1.10948(5) 0.01534(18) Uani 1 1 d . . . . .
H1O H 0.4552(6) 0.230(2) 1.0988(12) 0.034(4) Uiso 1 1 d . . . . .
O2 O 0.44709(3) 0.29148(8) 0.94658(5) 0.01268(18) Uani 1 1 d . . . . .
N1 N 0.43149(3) -0.14677(10) 0.93469(7) 0.0144(2) Uani 1 1 d . . . . .
C8A C 0.41139(4) 0.45227(11) 0.73380(7) 0.0107(2) Uani 1 1 d . . . . .
C9A C 0.41208(4) 0.52017(11) 0.64935(7) 0.0107(2) Uani 1 1 d . . . . .
C10A C 0.36733(4) 0.55132(12) 0.57936(7) 0.0126(2) Uani 1 1 d . . . . .
C11A C 0.32198(4) 0.51724(13) 0.59421(8) 0.0159(2) Uani 1 1 d . . . . .
H11A H 0.291544 0.539665 0.546996 0.019 Uiso 1 1 calc R U . . .
C12A C 0.32171(4) 0.44987(13) 0.67907(8) 0.0168(2) Uani 1 1 d . . . . .
H12A H 0.290803 0.426236 0.689604 0.020 Uiso 1 1 calc R U . . .
C13A C 0.36601(4) 0.41654(12) 0.74881(8) 0.0142(2) Uani 1 1 d . . . . .
H13A H 0.365352 0.369731 0.806273 0.017 Uiso 1 1 calc R U . . .
O3A O 0.45640(3) 0.42227(8) 0.79924(5) 0.01282(18) Uani 1 1 d . . . . .
H2O H 0.4516(7) 0.374(2) 0.8531(13) 0.043(5) Uiso 1 1 d . . . . .
O4A O 0.45549(3) 0.56065(9) 0.63061(6) 0.01373(18) Uani 1 1 d . . . . .
H3O H 0.4815(7) 0.5131(19) 0.6648(13) 0.037(5) Uiso 1 1 d . . . . .
O5A O 0.36726(3) 0.61355(9) 0.49454(5) 0.01565(18) Uani 1 1 d . . . . .
H40 H 0.3971(7) 0.629(2) 0.4928(13) 0.039(5) Uiso 1 1 d . . . . .
C8B C 0.30615(4) 1.02767(13) 0.28780(8) 0.0172(2) Uani 1 1 d . . . . .
C9B C 0.30945(4) 0.94795(13) 0.37025(8) 0.0148(2) Uani 1 1 d . . . . .
C10B C 0.30958(4) 1.01835(13) 0.45470(8) 0.0171(2) Uani 1 1 d . . . . .
C11B C 0.30578(4) 1.16756(14) 0.45566(9) 0.0213(3) Uani 1 1 d . . . . .
H11B H 0.305663 1.216281 0.512810 0.026 Uiso 1 1 calc R U . . .
C12B C 0.30212(4) 1.24557(14) 0.37222(10) 0.0234(3) Uani 1 1 d . . . . .
H12B H 0.299365 1.347647 0.373056 0.028 Uiso 1 1 calc R U . . .
C13B C 0.30244(4) 1.17663(14) 0.28774(9) 0.0217(3) Uani 1 1 d . . . . .
H13B H 0.300172 1.230551 0.231318 0.026 Uiso 1 1 calc R U . . .
O3B O 0.30700(3) 0.95430(11) 0.20586(6) 0.0233(2) Uani 1 1 d . . . . .
H5O H 0.3088(7) 0.861(2) 0.2211(14) 0.047(5) Uiso 1 1 d . . . . .
O4B O 0.31178(3) 0.80175(9) 0.36250(6) 0.01821(19) Uani 1 1 d . . . . .
H6O H 0.3236(7) 0.760(2) 0.4197(15) 0.048(5) Uiso 1 1 d . . . . .
O5B O 0.31351(3) 0.92959(10) 0.53142(6) 0.0233(2) Uani 1 1 d . . . . .
H7O H 0.3116(7) 0.978(2) 0.5838(15) 0.049(5) Uiso 1 1 d . . . . .
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'
loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
N1 C1 C2 119.14(10) . . ?
N1 C1 C7 119.42(10) . . ?
C2 C1 C7 121.44(10) . . ?
O1 C2 C1 118.57(9) . . ?
O1 C2 C3 119.82(10) . . ?
C1 C2 C3 121.60(10) . . ?
O2 C3 C4 124.42(10) . . ?
O2 C3 C2 119.35(9) . . ?
C4 C3 C2 116.23(10) . . ?
C5 C4 C3 120.68(10) . . ?
C5 C4 H4 119.7 . . ?
C3 C4 H4 119.7 . . ?
N1 C5 C4 121.54(10) . . ?
N1 C5 H5 119.2 . . ?
C4 C5 H5 119.2 . . ?
N1 C6 H6A 109.5 . . ?
N1 C6 H6B 109.5 . . ?
H6A C6 H6B 109.5 . . ?
N1 C6 H6C 109.5 . . ?
H6A C6 H6C 109.5 . . ?
H6B C6 H6C 109.5 . . ?
C1 C7 H7A 109.5 . . ?
C1 C7 H7B 109.5 . . ?
H7A C7 H7B 109.5 . . ?
C1 C7 H7C 109.5 . . ?
H7A C7 H7C 109.5 . . ?
H7B C7 H7C 109.5 . . ?
C2 O1 H1O 106.6(11) . . ?
C5 N1 C1 120.80(10) . . ?
C5 N1 C6 119.15(10) . . ?
C1 N1 C6 120.03(10) . . ?
O3A C8A C9A 117.44(9) . . ?
O3A C8A C13A 122.65(9) . . ?
C9A C8A C13A 119.92(9) . . ?
O4A C9A C8A 122.93(9) . . ?
O4A C9A C10A 117.11(9) . . ?
C8A C9A C10A 119.95(9) . . ?
O5A C10A C11A 118.71(9) . . ?
O5A C10A C9A 120.84(9) . . ?
C11A C10A C9A 120.44(10) . . ?
C10A C11A C12A 119.13(10) . . ?
C10A C11A H11A 120.4 . . ?
C12A C11A H11A 120.4 . . ?
C11A C12A C13A 121.01(10) . . ?
C11A C12A H12A 119.5 . . ?
C13A C12A H12A 119.5 . . ?
C12A C13A C8A 119.55(10) . . ?
C12A C13A H13A 120.2 . . ?
C8A C13A H13A 120.2 . . ?
C8A O3A H2O 110.4(11) . . ?
C9A O4A H3O 112.8(12) . . ?
C10A O5A H40 110.9(12) . . ?
O3B C8B C13B 120.69(11) . . ?
O3B C8B C9B 118.27(11) . . ?
C13B C8B C9B 121.04(11) . . ?
O4B C9B C8B 116.64(10) . . ?
O4B C9B C10B 123.44(10) . . ?
C8B C9B C10B 119.91(11) . . ?
O5B C10B C11B 125.39(11) . . ?
O5B C10B C9B 114.93(10) . . ?
C11B C10B C9B 119.68(11) . . ?
C10B C11B C12B 119.61(11) . . ?
C10B C11B H11B 120.2 . . ?
C12B C11B H11B 120.2 . . ?
C13B C12B C11B 121.23(12) . . ?
C13B C12B H12B 119.4 . . ?
C11B C12B H12B 119.4 . . ?
C8B C13B C12B 118.51(11) . . ?
C8B C13B H13B 120.7 . . ?
C12B C13B H13B 120.7 . . ?
C8B O3B H5O 106.0(12) . . ?
C9B O4B H6O 111.4(13) . . ?
C10B O5B H7O 112.4(13) . . ?
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
C1 N1 1.3741(14) . ?
C1 C2 1.3753(16) . ?
C1 C7 1.4924(15) . ?
C2 O1 1.3593(13) . ?
C2 C3 1.4238(15) . ?
C3 O2 1.2957(14) . ?
C3 C4 1.4084(15) . ?
C4 C5 1.3643(17) . ?
C4 H4 0.9500 . ?
C5 N1 1.3513(15) . ?
C5 H5 0.9500 . ?
C6 N1 1.4752(15) . ?
C6 H6A 0.9800 . ?
C6 H6B 0.9800 . ?
C6 H6C 0.9800 . ?
C7 H7A 0.9800 . ?
C7 H7B 0.9800 . ?
C7 H7C 0.9800 . ?
O1 H1O 0.872(19) . ?
C8A O3A 1.3701(12) . ?
C8A C9A 1.3901(15) . ?
C8A C13A 1.3940(15) . ?
C9A O4A 1.3769(12) . ?
C9A C10A 1.3969(15) . ?
C10A O5A 1.3662(13) . ?
C10A C11A 1.3888(15) . ?
C11A C12A 1.3901(16) . ?
C11A H11A 0.9500 . ?
C12A C13A 1.3909(16) . ?
C12A H12A 0.9500 . ?
C13A H13A 0.9500 . ?
O3A H2O 0.95(2) . ?
O4A H3O 0.872(19) . ?
O5A H40 0.858(19) . ?
C8B O3B 1.3831(15) . ?
C8B C13B 1.3850(18) . ?
C8B C9B 1.3928(16) . ?
C9B O4B 1.3634(14) . ?
C9B C10B 1.3947(16) . ?
C10B O5B 1.3684(15) . ?
C10B C11B 1.3880(18) . ?
C11B C12B 1.3950(19) . ?
C11B H11B 0.9500 . ?
C12B C13B 1.3920(19) . ?
C12B H12B 0.9500 . ?
C13B H13B 0.9500 . ?
O3B H5O 0.89(2) . ?
O4B H6O 0.89(2) . ?
O5B H7O 0.91(2) . ?
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_site_symmetry_A
_geom_hbond_publ_flag
O1 H1O O4A 0.872(19) 1.992(19) 2.8029(12) 154(2) 6_566 yes
O3A H2O O2 0.95(2) 1.60(2) 2.5498(10) 177(2) . yes
O4A H3O O3A 0.872(19) 1.868(19) 2.7059(11) 161(2) 2_656 yes
O5A H40 O2 0.858(19) 1.877(19) 2.6846(11) 156(2) 6_565 yes
O3B H5O O4B 0.89(2) 2.11(2) 2.6595(12) 119(2) . yes
O4B H6O O5A 0.89(2) 1.94(2) 2.7249(11) 146(2) . yes
O5B H7O O3B 0.91(2) 1.93(2) 2.8213(12) 169(2) 6_576 yes
C6 H6C O2 0.98 2.59 3.4416(14) 145 5_657 yes
C13A H13A O4B 0.95 2.49 3.2642(13) 139 6_566 yes
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
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
N1 C1 C2 O1 -178.89(9) . . . . ?
C7 C1 C2 O1 1.11(15) . . . . ?
N1 C1 C2 C3 -0.14(15) . . . . ?
C7 C1 C2 C3 179.86(9) . . . . ?
O1 C2 C3 O2 0.05(14) . . . . ?
C1 C2 C3 O2 -178.69(9) . . . . ?
O1 C2 C3 C4 179.91(9) . . . . ?
C1 C2 C3 C4 1.17(15) . . . . ?
O2 C3 C4 C5 178.42(10) . . . . ?
C2 C3 C4 C5 -1.43(15) . . . . ?
C3 C4 C5 N1 0.69(17) . . . . ?
C4 C5 N1 C1 0.43(16) . . . . ?
C4 C5 N1 C6 -178.18(10) . . . . ?
C2 C1 N1 C5 -0.69(15) . . . . ?
C7 C1 N1 C5 179.31(9) . . . . ?
C2 C1 N1 C6 177.90(9) . . . . ?
C7 C1 N1 C6 -2.10(15) . . . . ?
O3A C8A C9A O4A -1.61(15) . . . . ?
C13A C8A C9A O4A 178.86(10) . . . . ?
O3A C8A C9A C10A 178.97(9) . . . . ?
C13A C8A C9A C10A -0.56(15) . . . . ?
O4A C9A C10A O5A 2.79(15) . . . . ?
C8A C9A C10A O5A -177.76(9) . . . . ?
O4A C9A C10A C11A -178.29(10) . . . . ?
C8A C9A C10A C11A 1.16(16) . . . . ?
O5A C10A C11A C12A 178.05(10) . . . . ?
C9A C10A C11A C12A -0.90(17) . . . . ?
C10A C11A C12A C13A 0.05(17) . . . . ?
C11A C12A C13A C8A 0.55(17) . . . . ?
O3A C8A C13A C12A -179.79(10) . . . . ?
C9A C8A C13A C12A -0.29(16) . . . . ?
O3B C8B C9B O4B -1.93(15) . . . . ?
C13B C8B C9B O4B 178.50(10) . . . . ?
O3B C8B C9B C10B 178.90(10) . . . . ?
C13B C8B C9B C10B -0.67(16) . . . . ?
O4B C9B C10B O5B 1.57(15) . . . . ?
C8B C9B C10B O5B -179.32(9) . . . . ?
O4B C9B C10B C11B -178.31(10) . . . . ?
C8B C9B C10B C11B 0.81(16) . . . . ?
O5B C10B C11B C12B 179.81(10) . . . . ?
C9B C10B C11B C12B -0.33(17) . . . . ?
C10B C11B C12B C13B -0.30(17) . . . . ?
O3B C8B C13B C12B -179.51(10) . . . . ?
C9B C8B C13B C12B 0.05(17) . . . . ?
C11B C12B C13B C8B 0.44(17) . . . . ?

_cod_database_fobs_code 2022898
