#------------------------------------------------------------------------------
#$Date: 2023-10-10 05:19:25 +0300 (Tue, 10 Oct 2023) $
#$Revision: 286864 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/02/28/2022893.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_2022893
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, 0.5(C6 H6 O2)'
_chemical_formula_sum            'C10 H12 N O3'
_chemical_formula_weight         194.21
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_atom_sites_solution_hydrogens   mixed
_audit_creation_method           SHELXL-2014/7
_cell_angle_alpha                72.4243(4)
_cell_angle_beta                 85.7351(4)
_cell_angle_gamma                73.9285(4)
_cell_formula_units_Z            2
_cell_length_a                   6.83171(9)
_cell_length_b                   7.09634(10)
_cell_length_c                   10.01294(14)
_cell_measurement_reflns_used    8964
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      30.54
_cell_measurement_theta_min      3.10
_cell_volume                     444.659(11)
_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  'SHELXL2014 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT (Sheldrick, 2015)'
_diffrn_ambient_temperature      100(2)
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.998
_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  0.0240
_diffrn_reflns_av_unetI/netI     0.0239
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            11173
_diffrn_reflns_point_group_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         30.537
_diffrn_reflns_theta_min         2.134
_exptl_absorpt_coefficient_mu    0.108
_exptl_absorpt_correction_T_max  0.7461
_exptl_absorpt_correction_T_min  0.7189
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS, Bruker,2016'
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.450
_exptl_crystal_description       block
_exptl_crystal_F_000             206
_exptl_crystal_size_max          0.410
_exptl_crystal_size_mid          0.380
_exptl_crystal_size_min          0.220
_refine_diff_density_max         0.452
_refine_diff_density_min         -0.264
_refine_diff_density_rms         0.055
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.048
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     137
_refine_ls_number_reflns         2708
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.048
_refine_ls_R_factor_all          0.0395
_refine_ls_R_factor_gt           0.0364
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.0512P)²+0.1917P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1001
_refine_ls_wR_factor_ref         0.1023
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2471
_reflns_number_total             2708
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            lo5093sup1.cif
_cod_data_source_block           KA254_0M_def-hq_1_0.5
_cod_original_cell_volume        444.660(11)
_cod_database_code               2022893
_shelx_shelxl_version_number     2014/7
_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   0.957
_shelx_estimated_absorpt_t_max   0.977
loop_
_space_group_symop_operation_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_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 1.06764(12) 0.64378(13) 0.60013(8) 0.00925(16) Uani 1 1 d . . . . .
C2 C 0.86615(13) 0.75480(13) 0.57949(8) 0.00904(16) Uani 1 1 d . . . . .
C3 C 0.71807(12) 0.73275(13) 0.68833(9) 0.00915(16) Uani 1 1 d . . . . .
C4 C 0.79096(13) 0.58247(13) 0.81665(9) 0.01072(16) Uani 1 1 d . . . . .
H4 H 0.6997 0.5572 0.8922 0.013 Uiso 1 1 calc R U . . .
C5 C 0.99177(13) 0.47335(13) 0.83276(9) 0.01053(16) Uani 1 1 d . . . . .
H5 H 1.0366 0.3727 0.9195 0.013 Uiso 1 1 calc R U . . .
C6 C 1.34255(13) 0.38421(14) 0.75540(10) 0.01397(18) Uani 1 1 d . . . . .
H6A H 1.3790 0.2921 0.6963 0.021 Uiso 1 1 calc R U . . .
H6B H 1.3606 0.3031 0.8542 0.021 Uiso 1 1 calc R U . . .
H6C H 1.4306 0.4774 0.7333 0.021 Uiso 1 1 calc R U . . .
C7 C 1.22236(13) 0.66929(14) 0.48694(9) 0.01321(17) Uani 1 1 d . . . . .
H7A H 1.1544 0.7622 0.3994 0.020 Uiso 1 1 calc R U . . .
H7B H 1.2910 0.5355 0.4736 0.020 Uiso 1 1 calc R U . . .
H7C H 1.3229 0.7270 0.5137 0.020 Uiso 1 1 calc R U . . .
N1 N 1.12814(11) 0.50447(11) 0.72884(8) 0.00952(15) Uani 1 1 d . . . . .
O1 O 0.80721(10) 0.88597(10) 0.45067(7) 0.01354(15) Uani 1 1 d . . . . .
H1O H 0.677(3) 0.949(3) 0.452(2) 0.052(6) Uiso 1 1 d . . . . .
O2 O 0.53234(10) 0.84161(10) 0.66573(7) 0.01308(15) Uani 1 1 d . . . . .
C8 C 0.20047(12) 0.92636(13) 0.95892(8) 0.00975(16) Uani 1 1 d . . . . .
C9 C 0.03678(13) 0.95351(13) 0.87318(8) 0.01011(16) Uani 1 1 d . . . . .
H9 H 0.0612 0.9223 0.7866 0.012 Uiso 1 1 calc R U . . .
C10 C -0.16245(13) 1.02634(13) 0.91429(9) 0.01028(16) Uani 1 1 d . . . . .
H10 H -0.2732 1.0439 0.8556 0.012 Uiso 1 1 calc R U . . .
O3 O 0.39904(10) 0.85127(11) 0.92593(7) 0.01518(15) Uani 1 1 d . . . . .
H2O H 0.412(3) 0.851(3) 0.840(2) 0.041(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 118.91(8) . . ?
N1 C1 C7 118.94(7) . . ?
C2 C1 C7 122.15(7) . . ?
O1 C2 C1 118.26(7) . . ?
O1 C2 C3 119.45(7) . . ?
C1 C2 C3 122.28(8) . . ?
O2 C3 C4 124.12(8) . . ?
O2 C3 C2 120.44(8) . . ?
C4 C3 C2 115.42(7) . . ?
C5 C4 C3 120.61(8) . . ?
C5 C4 H4 119.7 . . ?
C3 C4 H4 119.7 . . ?
N1 C5 C4 122.01(8) . . ?
N1 C5 H5 119.0 . . ?
C4 C5 H5 119.0 . . ?
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 . . ?
C5 N1 C1 120.70(7) . . ?
C5 N1 C6 118.77(7) . . ?
C1 N1 C6 120.53(7) . . ?
C2 O1 H1O 109.2(13) . . ?
O3 C8 C9 122.95(8) . . ?
O3 C8 C10 117.73(8) . 2_577 ?
C9 C8 C10 119.31(7) . 2_577 ?
C10 C9 C8 120.17(7) . . ?
C10 C9 H9 119.9 . . ?
C8 C9 H9 119.9 . . ?
C9 C10 C8 120.52(8) . 2_577 ?
C9 C10 H10 119.7 . . ?
C8 C10 H10 119.7 2_577 . ?
C8 O3 H2O 112.1(12) . . ?
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 1.3757(10) . ?
C1 C2 1.3790(11) . ?
C1 C7 1.4961(12) . ?
C2 O1 1.3554(10) . ?
C2 C3 1.4339(11) . ?
C3 O2 1.2855(10) . ?
C3 C4 1.4177(11) . ?
C4 C5 1.3700(11) . ?
C4 H4 0.9500 . ?
C5 N1 1.3529(11) . ?
C5 H5 0.9500 . ?
C6 N1 1.4742(11) . ?
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 0.88(2) . ?
C8 O3 1.3685(10) . ?
C8 C9 1.3959(12) . ?
C8 C10 1.3971(12) 2_577 ?
C9 C10 1.3946(11) . ?
C9 H9 0.9500 . ?
C10 C8 1.3970(12) 2_577 ?
C10 H10 0.9500 . ?
O3 H2O 0.86(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
O1 H1O O2 0.88(2) 1.91(2) 2.6523(9) 140.7(18) 2_676
O3 H2O O2 0.86(2) 1.88(2) 2.7097(9) 160.6(18) .
C4 H4 O3 0.95 2.58 3.1625(11) 120.2 .
C7 H7C O2 0.98 2.60 3.5361(12) 160.6 1_655
C9 H9 O1 0.95 2.59 3.2978(10) 131.5 2_676
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 -177.62(7) . . . . ?
C7 C1 C2 O1 2.13(13) . . . . ?
N1 C1 C2 C3 1.13(13) . . . . ?
C7 C1 C2 C3 -179.13(8) . . . . ?
O1 C2 C3 O2 -2.48(13) . . . . ?
C1 C2 C3 O2 178.79(8) . . . . ?
O1 C2 C3 C4 176.02(7) . . . . ?
C1 C2 C3 C4 -2.71(12) . . . . ?
O2 C3 C4 C5 -179.66(8) . . . . ?
C2 C3 C4 C5 1.90(12) . . . . ?
C3 C4 C5 N1 0.48(14) . . . . ?
C4 C5 N1 C1 -2.23(13) . . . . ?
C4 C5 N1 C6 178.60(8) . . . . ?
C2 C1 N1 C5 1.40(12) . . . . ?
C7 C1 N1 C5 -178.35(8) . . . . ?
C2 C1 N1 C6 -179.45(8) . . . . ?
C7 C1 N1 C6 0.80(12) . . . . ?
O3 C8 C9 C10 178.52(8) . . . . ?
C10 C8 C9 C10 -0.26(14) 2_577 . . . ?
C8 C9 C10 C8 0.26(14) . . . 2_577 ?

_cod_database_fobs_code 2022893
