#------------------------------------------------------------------------------
#$Date: 2025-08-18 18:33:07 +0300 (Mon, 18 Aug 2025) $
#$Revision: 301779 $
#$URL: file:///home/coder/svn-repositories/cod/cif/1/54/58/1545835.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_1545835
loop_
_publ_author_name
'Bolla, Geetha'
'Nangia, Ashwini'
_publ_section_title
;
 Binary and ternary cocrystals of sulfa drug acetazolamide with pyridine
 carboxamides and cyclic amides
;
_journal_coeditor_code           ED5007
_journal_issue                   2
_journal_name_full               IUCrJ
_journal_page_first              152
_journal_page_last               160
_journal_paper_doi               10.1107/S2052252516000543
_journal_volume                  3
_journal_year                    2016
_chemical_formula_moiety         C4H6N4O3S2,C6H6N2O
_chemical_formula_sum            'C10 H12 N6 O4 S2'
_chemical_formula_weight         344.38
_chemical_melting_point          453
_chemical_name_common            ACETAZOLAMIDE;NICOTINAMIDE
_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           SHELXL-97
_cell_angle_alpha                69.797(11)
_cell_angle_beta                 85.463(12)
_cell_angle_gamma                81.889(12)
_cell_formula_units_Z            2
_cell_length_a                   5.1477(8)
_cell_length_b                   10.8147(14)
_cell_length_c                   14.2604(16)
_cell_measurement_reflns_used    1270
_cell_measurement_temperature    298(2)
_cell_measurement_theta_max      71.6760
_cell_measurement_theta_min      4.3720
_cell_volume                     737.20(18)
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      298(2)
_diffrn_detector_area_resol_mean '\w scans'
_diffrn_measured_fraction_theta_full 0.995
_diffrn_measured_fraction_theta_max 0.995
_diffrn_measurement_device_type  'Xcalibur, Eos, Gemini'
_diffrn_measurement_method       multi-scan
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0409
_diffrn_reflns_av_sigmaI/netI    0.0584
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_h_min       -3
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            4027
_diffrn_reflns_theta_full        67.07
_diffrn_reflns_theta_max         67.07
_diffrn_reflns_theta_min         3.30
_exptl_absorpt_coefficient_mu    3.554
_exptl_crystal_colour            COLORLES
_exptl_crystal_density_diffrn    1.551
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       BLOCK
_exptl_crystal_F_000             356
_exptl_crystal_size_max          0.22
_exptl_crystal_size_mid          0.21
_exptl_crystal_size_min          0.20
_refine_diff_density_max         0.407
_refine_diff_density_min         -0.590
_refine_diff_density_rms         0.075
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.006
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     220
_refine_ls_number_reflns         2607
_refine_ls_number_restraints     2
_refine_ls_restrained_S_all      1.006
_refine_ls_R_factor_all          0.0819
_refine_ls_R_factor_gt           0.0626
_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)+(0.1157P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1722
_refine_ls_wR_factor_ref         0.1935
_reflns_number_gt                1906
_reflns_number_total             2607
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ed5007.cif
_cod_data_source_block           ACZNAM11
_cod_original_cell_volume        737.20(17)
_cod_database_code               1545835
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 0.1492(2) 0.93431(10) 0.78260(8) 0.0528(4) Uani 1 1 d .
S2 S 0.5163(2) 0.78104(10) 0.67044(7) 0.0515(3) Uani 1 1 d .
N2 N 0.7184(7) 0.9964(3) 0.5809(2) 0.0533(9) Uani 1 1 d .
N3 N 0.9226(8) 0.8215(4) 0.5326(3) 0.0529(9) Uani 1 1 d .
N1 N 0.5204(7) 1.0284(3) 0.6423(3) 0.0543(9) Uani 1 1 d .
O1 O 0.8030(8) 0.6179(3) 0.5851(3) 0.0872(12) Uani 1 1 d .
O3 O 0.0075(6) 1.0630(3) 0.7454(3) 0.0690(9) Uani 1 1 d .
O2 O 0.0271(6) 0.8176(3) 0.7988(2) 0.0673(9) Uani 1 1 d .
N4 N 0.2823(9) 0.9208(5) 0.8817(3) 0.0592(10) Uani 1 1 d .
C2 C 0.7357(8) 0.8725(4) 0.5871(3) 0.0479(10) Uani 1 1 d .
C3 C 0.9479(10) 0.6950(5) 0.5328(4) 0.0637(12) Uani 1 1 d .
C1 C 0.4034(8) 0.9263(4) 0.6926(3) 0.0487(10) Uani 1 1 d .
C4 C 1.1615(13) 0.6621(5) 0.4648(5) 0.0875(19) Uani 1 1 d .
H4A H 1.2521 0.5757 0.4980 0.131 Uiso 1 1 calc R
H4B H 1.2829 0.7269 0.4477 0.131 Uiso 1 1 calc R
H4C H 1.0867 0.6627 0.4051 0.131 Uiso 1 1 calc R
O4 O 1.3130(6) 0.6472(3) 0.0123(2) 0.0590(8) Uani 1 1 d .
N6 N 1.2270(8) 0.4391(4) 0.0931(3) 0.0561(10) Uani 1 1 d D
C5 C 0.9382(8) 0.6198(4) 0.1226(3) 0.0479(9) Uani 1 1 d .
C10 C 1.1739(8) 0.5686(4) 0.0720(3) 0.0481(10) Uani 1 1 d .
N5 N 0.6488(8) 0.8116(4) 0.1285(3) 0.0655(11) Uani 1 1 d .
C6 C 0.8526(9) 0.7547(4) 0.0894(4) 0.0623(12) Uani 1 1 d .
H6 H 0.9449 0.8090 0.0360 0.075 Uiso 1 1 calc R
C9 C 0.8006(9) 0.5412(5) 0.2017(3) 0.0628(12) Uani 1 1 d .
H9 H 0.8511 0.4501 0.2270 0.075 Uiso 1 1 calc R
C7 C 0.5195(10) 0.7322(5) 0.2058(4) 0.0676(13) Uani 1 1 d .
H7 H 0.3773 0.7703 0.2351 0.081 Uiso 1 1 calc R
C8 C 0.5864(11) 0.5979(5) 0.2438(4) 0.0727(15) Uani 1 1 d .
H8 H 0.4897 0.5457 0.2969 0.087 Uiso 1 1 calc R
H6B H 1.360(6) 0.411(4) 0.066(3) 0.052(13) Uiso 1 1 d D
H3A H 1.028(9) 0.870(4) 0.506(3) 0.053(13) Uiso 1 1 d .
H6A H 1.125(7) 0.384(4) 0.128(3) 0.058(13) Uiso 1 1 d D
H4F H 0.328(8) 0.986(5) 0.885(3) 0.046(13) Uiso 1 1 d .
H4E H 0.320(10) 0.845(5) 0.918(4) 0.071(17) 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 0.0181 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
O3 S1 O2 121.4(2)
O3 S1 N4 108.5(2)
O2 S1 N4 108.5(2)
O3 S1 C1 106.4(2)
O2 S1 C1 103.6(2)
N4 S1 C1 107.6(2)
C2 S2 C1 85.42(19)
C2 N2 N1 112.2(3)
C3 N3 C2 124.2(4)
C3 N3 H3A 122(3)
C2 N3 H3A 113(3)
C1 N1 N2 111.1(3)
S1 N4 H4F 117(3)
S1 N4 H4E 114(4)
H4F N4 H4E 128(5)
N2 C2 N3 120.8(4)
N2 C2 S2 115.1(3)
N3 C2 S2 124.0(3)
O1 C3 N3 120.3(4)
O1 C3 C4 124.7(5)
N3 C3 C4 115.0(4)
N1 C1 S2 116.2(3)
N1 C1 S1 121.7(3)
S2 C1 S1 122.0(2)
C3 C4 H4A 109.5
C3 C4 H4B 109.5
H4A C4 H4B 109.5
C3 C4 H4C 109.5
H4A C4 H4C 109.5
H4B C4 H4C 109.5
C10 N6 H6B 118(3)
C10 N6 H6A 124(3)
H6B N6 H6A 118(4)
C9 C5 C6 116.9(4)
C9 C5 C10 124.0(4)
C6 C5 C10 119.1(4)
O4 C10 N6 121.8(4)
O4 C10 C5 120.1(4)
N6 C10 C5 118.2(3)
C6 N5 C7 117.0(4)
N5 C6 C5 124.6(4)
N5 C6 H6 117.7
C5 C6 H6 117.7
C5 C9 C8 119.7(4)
C5 C9 H9 120.2
C8 C9 H9 120.2
N5 C7 C8 123.1(4)
N5 C7 H7 118.5
C8 C7 H7 118.5
C7 C8 C9 118.7(4)
C7 C8 H8 120.6
C9 C8 H8 120.6
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
S1 O3 1.419(3)
S1 O2 1.429(3)
S1 N4 1.572(4)
S1 C1 1.774(4)
S2 C2 1.719(4)
S2 C1 1.721(4)
N2 C2 1.302(5)
N2 N1 1.377(5)
N3 C3 1.355(6)
N3 C2 1.364(5)
N3 H3A 0.79(5)
N1 C1 1.292(5)
O1 C3 1.211(6)
N4 H4F 0.79(4)
N4 H4E 0.81(5)
C3 C4 1.495(7)
C4 H4A 0.9600
C4 H4B 0.9600
C4 H4C 0.9600
O4 C10 1.239(5)
N6 C10 1.319(5)
N6 H6B 0.832(19)
N6 H6A 0.846(19)
C5 C9 1.370(6)
C5 C6 1.386(6)
C5 C10 1.499(6)
N5 C6 1.323(6)
N5 C7 1.337(6)
C6 H6 0.9300
C9 C8 1.382(6)
C9 H9 0.9300
C7 C8 1.366(7)
C7 H7 0.9300
C8 H8 0.9300
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 PubChem 139049940
