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#$Date: 2025-08-22 17:52:37 +0200 (Fri, 22 Aug 2025) $
#$Revision: 301865 $
#$URL: svn://saulius.grazulis.lt/cod-secondary/cif/7/22/81/7228150.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_7228150
loop_
_publ_author_name
'Kumar, Vineet'
'Thaimattam, Ram'
'Dutta, Sanjay'
'Munshi, Parthapratim'
'Ramanan, A.'
_publ_section_title
;
 Structural landscape of multicomponent solids based on sulfa drugs
;
_journal_name_full               CrystEngComm
_journal_paper_doi               10.1039/C7CE00217C
_journal_year                    2017
_chemical_formula_moiety         'C10 H10 N3 O3 S, 0.5(C4 H12 N2)'
_chemical_formula_sum            'C12 H16 N4 O3 S'
_chemical_formula_weight         296.35
_space_group_IT_number           2
_symmetry_cell_setting           triclinic
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           'SHELXTL-NT2000 ver.6.12'
_audit_update_record
;
2016-10-18 deposited with the CCDC.
2017-04-28 downloaded from the CCDC.
;
_cell_angle_alpha                108.255(3)
_cell_angle_beta                 94.274(5)
_cell_angle_gamma                104.221(3)
_cell_formula_units_Z            2
_cell_length_a                   8.0883(15)
_cell_length_b                   8.2003(16)
_cell_length_c                   11.818(2)
_cell_measurement_reflns_used    1065
_cell_measurement_temperature    298(2)
_cell_measurement_theta_max      24.97
_cell_measurement_theta_min      2.63
_cell_volume                     711.7(2)
_computing_cell_refinement       'Bruker SMART'
_computing_data_collection       'Bruker SMART'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      298(2)
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0071
_diffrn_reflns_av_sigmaI/netI    0.0231
_diffrn_reflns_limit_h_max       4
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_l_max       7
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            2501
_diffrn_reflns_theta_full        24.98
_diffrn_reflns_theta_max         24.98
_diffrn_reflns_theta_min         1.84
_exptl_absorpt_coefficient_mu    0.240
_exptl_absorpt_correction_T_max  .937
_exptl_absorpt_correction_T_min  .740
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(SADABS; Bruker, 2000)'
_exptl_crystal_colour            green
_exptl_crystal_density_diffrn    1.383
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             312
_exptl_crystal_size_max          .42
_exptl_crystal_size_mid          .25
_exptl_crystal_size_min          .16
_refine_diff_density_max         0.474
_refine_diff_density_min         -0.590
_refine_diff_density_rms         0.111
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.091
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     182
_refine_ls_number_reflns         2501
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.091
_refine_ls_R_factor_all          0.0660
_refine_ls_R_factor_gt           0.0640
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.1441P)²+0.4411P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1905
_refine_ls_wR_factor_ref         0.1972
_reflns_number_gt                2501
_reflns_number_total             2501
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            c7ce00217c2.cif
_cod_data_source_block           j5am
_cod_database_code               7228150
loop_
_symmetry_equiv_pos_as_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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
S1 S 0.17224(11) 1.01148(10) 0.85018(8) 0.0363(5) Uani 1 1 d .
O2 O 0.2263(4) 1.0288(3) 0.9728(2) 0.0472(9) Uani 1 1 d .
O1 O 0.0801(3) 1.1353(3) 0.8324(2) 0.0408(8) Uani 1 1 d .
C1 C 0.3649(5) 1.1231(4) 0.6918(4) 0.0365(13) Uani 1 1 d .
H1 H 0.2705 1.1564 0.6665 0.044 Uiso 1 1 calc R
O3 O -0.1245(4) 0.7184(3) 0.4877(2) 0.0507(9) Uani 1 1 d .
C2 C -0.0297(5) 0.7446(4) 0.6705(3) 0.0346(10) Uani 1 1 d .
C3 C 0.3570(5) 1.0472(4) 0.7834(3) 0.0330(11) Uani 1 1 d .
N2 N 0.0588(4) 0.8078(3) 0.7872(3) 0.0386(10) Uani 1 1 d .
N1 N 0.8011(5) 1.1309(4) 0.6263(4) 0.0508(12) Uani 1 1 d .
H1A H 0.8901 1.1041 0.6512 0.061 Uiso 1 1 calc R
H1B H 0.8049 1.1786 0.5709 0.061 Uiso 1 1 calc R
C4 C 0.4987(5) 0.9957(4) 0.8186(3) 0.0352(13) Uani 1 1 d .
H4 H 0.4950 0.9442 0.8786 0.042 Uiso 1 1 calc R
C5 C -0.1522(5) 0.5744(4) 0.6156(4) 0.0457(12) Uani 1 1 d .
H5 H -0.1873 0.4866 0.6501 0.055 Uiso 1 1 calc R
N4 N 0.0148(5) 0.6473(4) 0.9571(3) 0.0522(11) Uani 1 1 d .
H4A H 0.0225 0.6915 0.8963 0.063 Uiso 1 1 calc R
H4B H 0.0171 0.7372 1.0251 0.063 Uiso 1 1 calc R
N3 N -0.0091(4) 0.8336(4) 0.5959(3) 0.0486(11) Uani 1 1 d .
C6 C 0.6532(5) 1.0979(4) 0.6750(4) 0.0376(13) Uani 1 1 d .
C7 C 0.5089(5) 1.1483(4) 0.6399(4) 0.0427(14) Uani 1 1 d .
H7 H 0.5122 1.1999 0.5800 0.051 Uiso 1 1 calc R
C8 C 0.6436(5) 1.0204(4) 0.7654(3) 0.0356(12) Uani 1 1 d .
H8 H 0.7370 0.9851 0.7898 0.043 Uiso 1 1 calc R
C9 C -0.2058(5) 0.5666(4) 0.5055(4) 0.0440(12) Uani 1 1 d .
C10 C 0.1635(6) 0.5783(5) 0.9720(4) 0.0550(14) Uani 1 1 d .
H10A H 0.2696 0.6756 0.9935 0.066 Uiso 1 1 calc R
H10B H 0.1678 0.4897 0.8962 0.066 Uiso 1 1 calc R
C11 C -0.1497(6) 0.5055(5) 0.9308(4) 0.0604(15) Uani 1 1 d .
H11A H -0.1571 0.4141 0.8535 0.072 Uiso 1 1 calc R
H11B H -0.2454 0.5559 0.9254 0.072 Uiso 1 1 calc R
C12 C -0.3326(6) 0.4291(5) 0.4007(4) 0.0603(14) Uani 1 1 d .
H12A H -0.3757 0.3222 0.4193 0.090 Uiso 1 1 calc R
H12B H -0.2768 0.4023 0.3310 0.090 Uiso 1 1 calc R
H12C H -0.4270 0.4744 0.3842 0.090 Uiso 1 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'
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'
S S 0.1246 0.1234 '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
O2 S1 O1 116.60(16) . .
O2 S1 N2 104.93(15) . .
O1 S1 N2 111.78(14) . .
O2 S1 C3 107.84(16) . .
O1 S1 C3 106.46(16) . .
N2 S1 C3 109.04(16) . .
C7 C1 C3 120.6(3) . .
C7 C1 H1 119.7 . .
C3 C1 H1 119.7 . .
C9 O3 N3 108.2(3) . .
N3 C2 N2 124.1(3) . .
N3 C2 C5 111.3(3) . .
N2 C2 C5 124.5(3) . .
C4 C3 C1 118.8(4) . .
C4 C3 S1 119.8(3) . .
C1 C3 S1 121.4(3) . .
C2 N2 S1 121.8(2) . .
C6 N1 H1A 120.0 . .
C6 N1 H1B 120.0 . .
H1A N1 H1B 120.0 . .
C8 C4 C3 120.4(3) . .
C8 C4 H4 119.8 . .
C3 C4 H4 119.8 . .
C9 C5 C2 105.5(3) . .
C9 C5 H5 127.3 . .
C2 C5 H5 127.3 . .
C10 N4 C11 111.2(3) . .
C10 N4 H4A 109.4 . .
C11 N4 H4A 109.4 . .
C10 N4 H4B 109.4 . .
C11 N4 H4B 109.4 . .
H4A N4 H4B 108.0 . .
C2 N3 O3 104.8(3) . .
N1 C6 C8 121.1(3) . .
N1 C6 C7 121.0(4) . .
C8 C6 C7 117.8(5) . .
C1 C7 C6 121.2(4) . .
C1 C7 H7 119.4 . .
C6 C7 H7 119.4 . .
C4 C8 C6 121.2(3) . .
C4 C8 H8 119.4 . .
C6 C8 H8 119.4 . .
C5 C9 O3 110.2(3) . .
C5 C9 C12 134.2(4) . .
O3 C9 C12 115.6(4) . .
N4 C10 C11 110.7(4) . 2_567
N4 C10 H10A 109.5 . .
C11 C10 H10A 109.5 2_567 .
N4 C10 H10B 109.5 . .
C11 C10 H10B 109.5 2_567 .
H10A C10 H10B 108.1 . .
N4 C11 C10 111.0(3) . 2_567
N4 C11 H11A 109.4 . .
C10 C11 H11A 109.4 2_567 .
N4 C11 H11B 109.4 . .
C10 C11 H11B 109.4 2_567 .
H11A C11 H11B 108.0 . .
C9 C12 H12A 109.5 . .
C9 C12 H12B 109.5 . .
H12A C12 H12B 109.5 . .
C9 C12 H12C 109.5 . .
H12A C12 H12C 109.5 . .
H12B C12 H12C 109.5 . .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
S1 O2 1.435(3) .
S1 O1 1.454(2) .
S1 N2 1.597(3) .
S1 C3 1.746(4) .
C1 C7 1.358(6) .
C1 C3 1.405(6) .
C1 H1 0.9300 .
O3 C9 1.345(5) .
O3 N3 1.425(4) .
C2 N3 1.304(5) .
C2 N2 1.381(4) .
C2 C5 1.417(4) .
C3 C4 1.394(5) .
N1 C6 1.370(6) .
N1 H1A 0.8600 .
N1 H1B 0.8600 .
C4 C8 1.372(5) .
C4 H4 0.9300 .
C5 C9 1.318(5) .
C5 H5 0.9300 .
N4 C10 1.470(6) .
N4 C11 1.474(5) .
N4 H4A 0.9000 .
N4 H4B 0.9000 .
C6 C8 1.402(6) .
C6 C7 1.407(5) .
C7 H7 0.9300 .
C8 H8 0.9300 .
C9 C12 1.492(5) .
C10 C11 1.510(6) 2_567
C10 H10A 0.9700 .
C10 H10B 0.9700 .
C11 C10 1.510(6) 2_567
C11 H11A 0.9700 .
C11 H11B 0.9700 .
C12 H12A 0.9600 .
C12 H12B 0.9600 .
C12 H12C 0.9600 .
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_4
C7 C1 C3 C4 -1.0(5) .
C7 C1 C3 S1 -179.3(2) .
O2 S1 C3 C4 32.6(3) .
O1 S1 C3 C4 158.5(2) .
N2 S1 C3 C4 -80.8(3) .
O2 S1 C3 C1 -149.1(3) .
O1 S1 C3 C1 -23.2(3) .
N2 S1 C3 C1 97.5(3) .
N3 C2 N2 S1 10.8(6) .
C5 C2 N2 S1 -170.2(3) .
O2 S1 N2 C2 173.8(3) .
O1 S1 N2 C2 46.5(4) .
C3 S1 N2 C2 -70.9(3) .
C1 C3 C4 C8 0.6(5) .
S1 C3 C4 C8 179.0(2) .
N3 C2 C5 C9 -0.9(5) .
N2 C2 C5 C9 180.0(4) .
N2 C2 N3 O3 179.9(3) .
C5 C2 N3 O3 0.8(4) .
C9 O3 N3 C2 -0.4(4) .
C3 C1 C7 C6 0.7(5) .
N1 C6 C7 C1 -177.0(3) .
C8 C6 C7 C1 0.1(5) .
C3 C4 C8 C6 0.1(5) .
N1 C6 C8 C4 176.6(3) .
C7 C6 C8 C4 -0.5(5) .
C2 C5 C9 O3 0.6(5) .
C2 C5 C9 C12 -179.6(5) .
N3 O3 C9 C5 -0.1(5) .
N3 O3 C9 C12 -179.9(3) .
C11 N4 C10 C11 -56.1(5) 2_567
C10 N4 C11 C10 56.3(6) 2_567
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 PubChem 139203456
