#------------------------------------------------------------------------------
#$Date: 2025-08-22 17:52:37 +0200 (Fri, 22 Aug 2025) $
#$Revision: 301865 $
#$URL: svn://saulius.grazulis.lt/cod-secondary/cif/7/22/81/7228152.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_7228152
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         'C11 H11 N4 O2 S, C5 H7 N2'
_chemical_formula_sum            'C16 H18 N6 O2 S'
_chemical_formula_weight         358.42
_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                101.990(6)
_cell_angle_beta                 103.624(7)
_cell_angle_gamma                103.701(6)
_cell_formula_units_Z            2
_cell_length_a                   7.871(2)
_cell_length_b                   9.438(3)
_cell_length_c                   12.417(4)
_cell_measurement_reflns_used    1267
_cell_measurement_temperature    298(2)
_cell_measurement_theta_max      23.70
_cell_measurement_theta_min      2.31
_cell_volume                     836.3(4)
_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  0.0128
_diffrn_reflns_av_sigmaI/netI    0.0366
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       6
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            2952
_diffrn_reflns_theta_full        24.99
_diffrn_reflns_theta_max         24.99
_diffrn_reflns_theta_min         1.76
_exptl_absorpt_coefficient_mu    0.218
_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            colorless
_exptl_crystal_density_diffrn    1.423
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             376
_exptl_crystal_size_max          .39
_exptl_crystal_size_mid          .23
_exptl_crystal_size_min          .14
_refine_diff_density_max         0.393
_refine_diff_density_min         -0.449
_refine_diff_density_rms         0.111
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.053
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     227
_refine_ls_number_reflns         2952
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.053
_refine_ls_R_factor_all          0.0808
_refine_ls_R_factor_gt           0.0613
_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)+(0.1399P)²+0.3574P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1668
_refine_ls_wR_factor_ref         0.2067
_reflns_number_gt                1706
_reflns_number_total             2952
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            c7ce00217c2.cif
_cod_data_source_block           sf4pacm
_cod_original_cell_volume        836.4(4)
_cod_database_code               7228152
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 1.02689(14) 0.16683(11) 0.71558(10) 0.0322(5) Uani 1 1 d .
O2 O 1.1292(4) 0.0845(3) 0.7774(3) 0.0432(10) Uani 1 1 d .
O1 O 1.0723(4) 0.1878(3) 0.6125(3) 0.0403(9) Uani 1 1 d .
N5 N 1.0736(5) 0.5702(4) 0.8632(3) 0.0338(10) Uani 1 1 d .
C1 C 0.7212(6) -0.0636(4) 0.5761(4) 0.0365(13) Uani 1 1 d .
H1 H 0.7943 -0.0869 0.5303 0.044 Uiso 1 1 calc R
N4 N 0.8799(6) 0.4174(4) 0.6750(4) 0.0344(11) Uani 1 1 d .
C2 C 0.7934(6) 0.0605(4) 0.6737(4) 0.0280(11) Uani 1 1 d .
C3 C 0.5413(6) -0.1526(5) 0.5470(4) 0.0351(13) Uani 1 1 d .
H3 H 0.4949 -0.2372 0.4829 0.042 Uiso 1 1 calc R
N2 N 0.7018(5) 0.6129(4) 0.9780(4) 0.0413(12) Uani 1 1 d .
H2 H 0.7832 0.6336 1.0435 0.050 Uiso 1 1 calc R
C4 C 0.9976(6) 0.4373(4) 0.7773(4) 0.0291(12) Uani 1 1 d .
N3 N 1.0575(5) 0.3216(4) 0.8085(3) 0.0351(11) Uani 1 1 d .
N6 N 0.2478(5) -0.2066(4) 0.5840(4) 0.0474(12) Uani 1 1 d .
H6A H 0.1801 -0.1848 0.6261 0.057 Uiso 1 1 calc R
H6B H 0.2037 -0.2839 0.5240 0.057 Uiso 1 1 calc R
C5 C 0.6829(6) 0.0948(5) 0.7408(4) 0.0361(13) Uani 1 1 d .
H5 H 0.7307 0.1762 0.8071 0.043 Uiso 1 1 calc R
C6 C 0.4436(6) 0.5461(5) 0.7668(4) 0.0311(13) Uani 1 1 d .
C7 C 0.5007(6) 0.0074(5) 0.7089(4) 0.0385(13) Uani 1 1 d .
H7 H 0.4259 0.0329 0.7528 0.046 Uiso 1 1 calc R
C8 C 0.4295(6) -0.1166(5) 0.6128(4) 0.0377(13) Uani 1 1 d .
C9 C 1.0265(7) 0.6906(5) 0.8407(5) 0.0428(15) Uani 1 1 d .
N1 N 0.3207(6) 0.5148(4) 0.6654(4) 0.0453(12) Uani 1 1 d .
H1A H 0.2795 0.4237 0.6204 0.054 Uiso 1 1 calc R
H1B H 0.2820 0.5856 0.6443 0.054 Uiso 1 1 calc R
C10 C 0.6416(8) 0.7221(6) 0.9459(5) 0.0434(15) Uani 1 1 d .
H10 H 0.6852 0.8197 0.9959 0.052 Uiso 1 1 calc R
C11 C 0.6368(7) 0.4706(5) 0.9089(5) 0.0381(13) Uani 1 1 d .
H11 H 0.6793 0.3951 0.9331 0.046 Uiso 1 1 calc R
C12 C 0.8360(7) 0.5402(5) 0.6574(5) 0.0428(14) Uani 1 1 d .
H12 H 0.7532 0.5303 0.5871 0.051 Uiso 1 1 calc R
C13 C 0.5118(8) 0.4346(5) 0.8057(5) 0.0439(16) Uani 1 1 d .
H13 H 0.4695 0.3349 0.7592 0.053 Uiso 1 1 calc R
C14 C 0.9054(8) 0.6805(5) 0.7365(5) 0.0441(15) Uani 1 1 d .
H14 H 0.8729 0.7643 0.7210 0.053 Uiso 1 1 calc R
C15 C 0.5216(8) 0.6952(5) 0.8449(5) 0.0472(16) Uani 1 1 d .
H15 H 0.4865 0.7753 0.8236 0.057 Uiso 1 1 calc R
C16 C 1.1098(8) 0.8370(5) 0.9342(5) 0.0619(17) Uani 1 1 d .
H16A H 1.0767 0.8247 1.0021 0.093 Uiso 1 1 calc R
H16B H 1.0653 0.9146 0.9091 0.093 Uiso 1 1 calc R
H16C H 1.2408 0.8657 0.9515 0.093 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
O2 S1 O1 114.9(2)
O2 S1 N3 105.1(2)
O1 S1 N3 113.57(19)
O2 S1 C2 106.8(2)
O1 S1 C2 107.6(2)
N3 S1 C2 108.50(19)
C9 N5 C4 116.3(5)
C3 C1 C2 120.3(4)
C3 C1 H1 119.9
C2 C1 H1 119.9
C12 N4 C4 115.6(4)
C5 C2 C1 119.4(4)
C5 C2 S1 120.4(3)
C1 C2 S1 120.2(3)
C1 C3 C8 120.4(4)
C1 C3 H3 119.8
C8 C3 H3 119.8
C10 N2 C11 120.4(5)
C10 N2 H2 119.8
C11 N2 H2 119.8
N4 C4 N5 125.7(4)
N4 C4 N3 122.6(4)
N5 C4 N3 111.6(5)
C4 N3 S1 121.5(3)
C8 N6 H6A 120.0
C8 N6 H6B 120.0
H6A N6 H6B 120.0
C2 C5 C7 119.9(4)
C2 C5 H5 120.0
C7 C5 H5 120.0
N1 C6 C13 122.4(5)
N1 C6 C15 123.2(5)
C13 C6 C15 114.4(5)
C8 C7 C5 120.7(4)
C8 C7 H7 119.6
C5 C7 H7 119.6
C7 C8 C3 119.3(4)
C7 C8 N6 120.2(4)
C3 C8 N6 120.6(4)
N5 C9 C14 121.9(4)
N5 C9 C16 116.7(6)
C14 C9 C16 121.4(5)
C6 N1 H1A 120.0
C6 N1 H1B 120.0
H1A N1 H1B 120.0
C15 C10 N2 121.4(5)
C15 C10 H10 119.3
N2 C10 H10 119.3
N2 C11 C13 121.4(5)
N2 C11 H11 119.3
C13 C11 H11 119.3
N4 C12 C14 124.0(6)
N4 C12 H12 118.0
C14 C12 H12 118.0
C11 C13 C6 120.7(5)
C11 C13 H13 119.6
C6 C13 H13 119.6
C12 C14 C9 116.4(5)
C12 C14 H14 121.8
C9 C14 H14 121.8
C10 C15 C6 121.7(5)
C10 C15 H15 119.2
C6 C15 H15 119.2
C9 C16 H16A 109.5
C9 C16 H16B 109.5
H16A C16 H16B 109.5
C9 C16 H16C 109.5
H16A C16 H16C 109.5
H16B C16 H16C 109.5
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
S1 O2 1.447(3)
S1 O1 1.447(3)
S1 N3 1.589(3)
S1 C2 1.764(4)
N5 C9 1.337(6)
N5 C4 1.362(5)
C1 C3 1.383(6)
C1 C2 1.391(6)
C1 H1 0.9300
N4 C12 1.331(6)
N4 C4 1.331(6)
C2 C5 1.385(6)
C3 C8 1.387(6)
C3 H3 0.9300
N2 C10 1.327(7)
N2 C11 1.338(6)
N2 H2 0.8600
C4 N3 1.378(6)
N6 C8 1.397(5)
N6 H6A 0.8600
N6 H6B 0.8600
C5 C7 1.390(6)
C5 H5 0.9300
C6 N1 1.321(6)
C6 C13 1.409(7)
C6 C15 1.429(6)
C7 C8 1.379(6)
C7 H7 0.9300
C9 C14 1.384(8)
C9 C16 1.494(6)
N1 H1A 0.8600
N1 H1B 0.8600
C10 C15 1.314(7)
C10 H10 0.9300
C11 C13 1.339(7)
C11 H11 0.9300
C12 C14 1.371(7)
C12 H12 0.9300
C13 H13 0.9300
C14 H14 0.9300
C15 H15 0.9300
C16 H16A 0.9600
C16 H16B 0.9600
C16 H16C 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
C3 C1 C2 C5 -0.5(7)
C3 C1 C2 S1 176.1(4)
O2 S1 C2 C5 95.5(4)
O1 S1 C2 C5 -140.6(4)
N3 S1 C2 C5 -17.4(5)
O2 S1 C2 C1 -81.1(4)
O1 S1 C2 C1 42.8(4)
N3 S1 C2 C1 166.1(4)
C2 C1 C3 C8 1.8(7)
C12 N4 C4 N5 0.4(6)
C12 N4 C4 N3 -179.5(4)
C9 N5 C4 N4 -1.1(6)
C9 N5 C4 N3 178.8(3)
N4 C4 N3 S1 14.1(5)
N5 C4 N3 S1 -165.8(3)
O2 S1 N3 C4 172.3(3)
O1 S1 N3 C4 45.9(4)
C2 S1 N3 C4 -73.7(4)
C1 C2 C5 C7 -1.5(7)
S1 C2 C5 C7 -178.0(4)
C2 C5 C7 C8 2.1(8)
C5 C7 C8 C3 -0.8(8)
C5 C7 C8 N6 177.7(5)
C1 C3 C8 C7 -1.2(8)
C1 C3 C8 N6 -179.7(4)
C4 N5 C9 C14 0.8(6)
C4 N5 C9 C16 -179.8(4)
C11 N2 C10 C15 -2.1(7)
C10 N2 C11 C13 0.8(6)
C4 N4 C12 C14 0.6(6)
N2 C11 C13 C6 -0.4(7)
N1 C6 C13 C11 179.8(4)
C15 C6 C13 C11 1.2(6)
N4 C12 C14 C9 -0.8(7)
N5 C9 C14 C12 0.0(7)
C16 C9 C14 C12 -179.4(4)
N2 C10 C15 C6 3.0(7)
N1 C6 C15 C10 179.0(4)
C13 C6 C15 C10 -2.4(6)
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 PubChem 139203458
