#------------------------------------------------------------------------------
#$Date: 2022-02-17 04:59:58 +0200 (Thu, 17 Feb 2022) $
#$Revision: 273002 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/02/25/2022566.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_2022566
loop_
_publ_author_name
'Shahbaz, Muhammad'
'Khan, Umair Ahmed'
'Chaudhary, M. Iqbal'
'Yousuf, Sammer'
_publ_section_title
;
 A new bioactive cocrystal of coumarin-3-carboxylic acid and thiourea:
 detailed structural features and biological activity studies
;
_journal_coeditor_code           OV3156
_journal_issue                   3
_journal_name_full               'Acta Crystallographica Section C'
_journal_page_first
;
;
_journal_paper_doi               10.1107/S205322962200081X
_journal_volume                  78
_journal_year                    2022
_chemical_formula_iupac          'C10 H6 O4, C H4 N2 S'
_chemical_formula_moiety         'C10 H6 O4, C H4 N2 S'
_chemical_formula_sum            'C11 H10 N2 O4 S'
_chemical_formula_weight         266.27
_chemical_name_common
;
Coumarin-3-carboxylic acid--thiourea (1/1)
;
_chemical_name_systematic
;
2-Oxochromene-3-carboxylic acid--thiourea (1/1)
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2yn'
_space_group_name_H-M_alt        'P 1 21/n 1'
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-2018/3
_cell_angle_alpha                90
_cell_angle_beta                 91.9050(10)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   11.0390(4)
_cell_length_b                   6.7554(2)
_cell_length_c                   15.6951(4)
_cell_measurement_reflns_used    7384
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      68.32
_cell_measurement_theta_min      4.82
_cell_volume                     1169.78(6)
_computing_cell_refinement
;
SAINT (Bruker, 2016)
;
_computing_data_collection
;
APEX3 (Bruker, 2016)
;
_computing_data_reduction
;
SAINT (Bruker, 2016)
;
_computing_molecular_graphics
;
SHELXTL (Bruker, 2016), ORTEP-3 for Windows (Farrugia,
2012)
and Mercury (Macrae et al., 2020)
;
_computing_publication_material
;
SHELXTL (Bruker, 2016), PLATON (Spek, 2020)
;
_computing_structure_refinement
;
SHELXL2018 (Sheldrick, 2015b)
;
_computing_structure_solution
;
SHELXT2014 (Sheldrick, 2015a)
;
_diffrn_ambient_temperature      293(2)
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.994
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.0536
_diffrn_reflns_av_unetI/netI     0.0331
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            14985
_diffrn_reflns_theta_full        67.679
_diffrn_reflns_theta_max         68.319
_diffrn_reflns_theta_min         4.823
_exptl_absorpt_coefficient_mu    2.574
_exptl_absorpt_correction_T_max  0.8820
_exptl_absorpt_correction_T_min  0.6270
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
(Blessing, 1995)
;
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.512
_exptl_crystal_description       block
_exptl_crystal_F_000             552
_exptl_crystal_size_max          0.20
_exptl_crystal_size_mid          0.08
_exptl_crystal_size_min          0.05
_refine_diff_density_max         0.306
_refine_diff_density_min         -0.361
_refine_ls_extinction_coef       0.0070(7)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method
;
SHELXL2018 (Sheldrick, 2015b)
;
_refine_ls_goodness_of_fit_ref   1.050
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     184
_refine_ls_number_reflns         2131
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.050
_refine_ls_R_factor_all          0.0447
_refine_ls_R_factor_gt           0.0373
_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)+(0.0538P)²+0.4417P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0962
_refine_ls_wR_factor_ref         0.1015
_reflns_number_gt                1837
_reflns_number_total             2131
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            ov3156sup1.cif
_cod_data_source_block           I
_cod_original_sg_symbol_H-M      'P 21/n'
_cod_database_code               2022566
_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.
;
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, -y-1/2, z-1/2'
loop_
_atom_site_type_symbol
_atom_site_label
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_calc_flag
_atom_site_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
S S1 0.52560(5) 0.12316(7) 0.22997(3) 0.0425(2) Uani d 1 . .
O O1 0.23789(11) 0.76206(18) 0.57140(7) 0.0329(3) Uani d 1 . .
O O2 0.32849(13) 0.4796(2) 0.59563(8) 0.0414(4) Uani d 1 . .
O O3 0.42709(12) 0.2827(2) 0.45638(8) 0.0381(3) Uani d 1 . .
O O4 0.38776(17) 0.4288(3) 0.33155(9) 0.0553(5) Uani d 1 . .
N N1 0.54529(16) -0.0809(3) 0.37445(10) 0.0364(4) Uani d 1 . .
N N2 0.6478(2) -0.2027(3) 0.26301(12) 0.0552(6) Uani d 1 . .
C C1 0.38209(16) 0.4166(3) 0.41498(11) 0.0318(4) Uani d 1 . .
C C2 0.31493(16) 0.5869(3) 0.45029(11) 0.0288(4) Uani d 1 . .
C C3 0.27019(16) 0.7320(3) 0.39856(11) 0.0306(4) Uani d 1 . .
H H3 0.279613 0.721317 0.340076 0.037 Uiso calc 1 . .
C C4 0.20913(16) 0.9007(3) 0.43099(11) 0.0294(4) Uani d 1 . .
C C5 0.16299(18) 1.0564(3) 0.38025(13) 0.0368(4) Uani d 1 . .
H H5 0.169816 1.051573 0.321381 0.044 Uiso calc 1 . .
C C6 0.10799(18) 1.2152(3) 0.41703(14) 0.0408(5) Uani d 1 . .
H H6 0.077090 1.317480 0.383123 0.049 Uiso calc 1 . .
C C7 0.09836(18) 1.2235(3) 0.50517(14) 0.0399(5) Uani d 1 . .
H H7 0.061458 1.332351 0.529651 0.048 Uiso calc 1 . .
C C8 0.14259(17) 1.0730(3) 0.55682(13) 0.0365(4) Uani d 1 . .
H H8 0.136115 1.079119 0.615686 0.044 Uiso calc 1 . .
C C9 0.19660(16) 0.9135(3) 0.51880(11) 0.0294(4) Uani d 1 . .
C C10 0.29784(15) 0.5981(3) 0.54205(11) 0.0289(4) Uani d 1 . .
C C11 0.57597(16) -0.0651(3) 0.29395(11) 0.0313(4) Uani d 1 . .
H H1A 0.506(2) 0.014(4) 0.3975(14) 0.040(6) Uiso d 1 . .
H H1B 0.571(2) -0.178(4) 0.4077(15) 0.050(7) Uiso d 1 . .
H H2A 0.677(2) -0.302(4) 0.2940(19) 0.070(8) Uiso d 1 . .
H H4A 0.427(3) 0.340(4) 0.3099(18) 0.070(9) Uiso d 1 . .
H H2B 0.672(3) -0.190(4) 0.210(2) 0.076(9) Uiso d 1 . .
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 '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 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
S S 0.3331 0.5567 '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_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle
_geom_angle_publ_flag
C10 O1 C9 . . 123.23(13) ?
C1 O4 H4A . . 114(2) ?
C11 N1 H1A . . 119.4(14) ?
C11 N1 H1B . . 122.7(15) ?
H1A N1 H1B . . 118(2) ?
C11 N2 H2A . . 122.8(18) ?
C11 N2 H2B . . 118.4(19) ?
H2A N2 H2B . . 119(3) ?
O3 C1 O4 . . 123.29(17) ?
O3 C1 C2 . . 125.39(16) ?
O4 C1 C2 . . 111.31(16) ?
C3 C2 C10 . . 119.77(16) ?
C3 C2 C1 . . 120.86(16) ?
C10 C2 C1 . . 119.37(15) ?
C2 C3 C4 . . 122.08(16) ?
C2 C3 H3 . . 119.0 ?
C4 C3 H3 . . 119.0 ?
C9 C4 C5 . . 117.93(17) ?
C9 C4 C3 . . 117.83(16) ?
C5 C4 C3 . . 124.23(17) ?
C6 C5 C4 . . 120.33(18) ?
C6 C5 H5 . . 119.8 ?
C4 C5 H5 . . 119.8 ?
C5 C6 C7 . . 119.99(18) ?
C5 C6 H6 . . 120.0 ?
C7 C6 H6 . . 120.0 ?
C8 C7 C6 . . 121.14(18) ?
C8 C7 H7 . . 119.4 ?
C6 C7 H7 . . 119.4 ?
C9 C8 C7 . . 118.16(18) ?
C9 C8 H8 . . 120.9 ?
C7 C8 H8 . . 120.9 ?
C8 C9 O1 . . 117.34(16) ?
C8 C9 C4 . . 122.44(17) ?
O1 C9 C4 . . 120.21(16) ?
O2 C10 O1 . . 115.39(15) ?
O2 C10 C2 . . 127.80(17) ?
O1 C10 C2 . . 116.80(15) ?
N1 C11 N2 . . 117.97(18) ?
N1 C11 S1 . . 122.29(15) ?
N2 C11 S1 . . 119.73(14) ?
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_site_symmetry_2
_geom_bond_distance
_geom_bond_publ_flag
S1 C11 . 1.7024(18) ?
O1 C10 . 1.377(2) ?
O1 C9 . 1.383(2) ?
O2 C10 . 1.201(2) ?
O3 C1 . 1.211(2) ?
O4 C1 . 1.316(2) ?
O4 H4A . 0.82(3) ?
N1 C11 . 1.323(2) ?
N1 H1A . 0.86(2) ?
N1 H1B . 0.88(3) ?
N2 C11 . 1.325(3) ?
N2 H2A . 0.88(3) ?
N2 H2B . 0.89(3) ?
C1 C2 . 1.486(2) ?
C2 C3 . 1.356(3) ?
C2 C10 . 1.461(2) ?
C3 C4 . 1.426(2) ?
C3 H3 . 0.9300 ?
C4 C9 . 1.392(2) ?
C4 C5 . 1.405(3) ?
C5 C6 . 1.370(3) ?
C5 H5 . 0.9300 ?
C6 C7 . 1.392(3) ?
C6 H6 . 0.9300 ?
C7 C8 . 1.379(3) ?
C7 H7 . 0.9300 ?
C8 C9 . 1.377(3) ?
C8 H8 . 0.9300 ?
loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_site_symmetry_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_publ_flag
C8 H8 S1 4_576 0.93 2.98 3.6742(19) 132.4 yes
N1 H1A O3 . 0.86(2) 2.23(3) 3.082(2) 172(2) yes
N1 H1B O2 3_656 0.88(3) 2.32(3) 3.062(2) 142(2) yes
N1 H1B O3 3_656 0.88(3) 2.25(2) 2.991(2) 142(2) yes
N2 H2A O2 3_656 0.88(3) 2.11(3) 2.907(2) 150(3) yes
N2 H2B O1 4_665 0.89(3) 2.37(3) 3.224(2) 162(3) yes
O4 H4A S1 . 0.82(3) 2.23(3) 3.0466(16) 170(3) 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_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion
_geom_torsion_publ_flag
O3 C1 C2 C3 . . . . 178.48(18) ?
O4 C1 C2 C3 . . . . -1.2(3) ?
O3 C1 C2 C10 . . . . -1.1(3) ?
O4 C1 C2 C10 . . . . 179.26(17) ?
C10 C2 C3 C4 . . . . 1.8(3) ?
C1 C2 C3 C4 . . . . -177.74(16) ?
C2 C3 C4 C9 . . . . 0.2(3) ?
C2 C3 C4 C5 . . . . 178.91(17) ?
C9 C4 C5 C6 . . . . 0.2(3) ?
C3 C4 C5 C6 . . . . -178.46(18) ?
C4 C5 C6 C7 . . . . 0.4(3) ?
C5 C6 C7 C8 . . . . -0.5(3) ?
C6 C7 C8 C9 . . . . -0.1(3) ?
C7 C8 C9 O1 . . . . -178.55(16) ?
C7 C8 C9 C4 . . . . 0.8(3) ?
C10 O1 C9 C8 . . . . -177.31(16) ?
C10 O1 C9 C4 . . . . 3.3(2) ?
C5 C4 C9 C8 . . . . -0.9(3) ?
C3 C4 C9 C8 . . . . 177.91(17) ?
C5 C4 C9 O1 . . . . 178.47(15) ?
C3 C4 C9 O1 . . . . -2.8(2) ?
C9 O1 C10 O2 . . . . 179.72(15) ?
C9 O1 C10 C2 . . . . -1.2(2) ?
C3 C2 C10 O2 . . . . 177.57(18) ?
C1 C2 C10 O2 . . . . -2.9(3) ?
C3 C2 C10 O1 . . . . -1.4(2) ?
C1 C2 C10 O1 . . . . 178.22(15) ?

_cod_database_fobs_code 2022566
