#------------------------------------------------------------------------------
#$Date: 2025-08-18 23:06:14 +0200 (Mon 18 de Aug de 2025) $
#$Revision: 301780 $
#$URL: svn://www.crystallography.net/cod/cif/1/55/18/1551862.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_1551862
loop_
_publ_author_name
'Bolla, Geetha'
'Nangia, Ashwini'
_publ_section_title
;
 Supramolecular synthon hierarchy in sulfonamide cocrystals with
 syn-amides and N-oxides
;
_journal_issue                   4
_journal_name_full               IUCrJ
_journal_page_first
;
;
_journal_paper_doi               10.1107/S2052252519005037
_journal_volume                  6
_journal_year                    2019
_chemical_formula_moiety         'C7 H8 Cl N3 O4 S2, C5 H5 N O'
_chemical_formula_sum            'C12 H13 Cl N4 O5 S2'
_chemical_formula_weight         392.83
_chemical_melting_point          407
_chemical_name_common            HCTHPFORMII
_space_group_crystal_system      orthorhombic
_space_group_IT_number           33
_space_group_name_Hall           'P 2c -2n'
_space_group_name_H-M_alt        'P n a 21'
_symmetry_space_group_name_Hall  'P 2c -2n'
_symmetry_space_group_name_H-M   'P n a 21'
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     direct
_audit_creation_date             2017-06-24
_audit_creation_method
;
Olex2 1.2
(compiled 2017.03.28 svn.r3405 for OlexSys, GUI svn.r5337)
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   29.442(4)
_cell_length_b                   7.3421(9)
_cell_length_c                   7.0867(7)
_cell_measurement_reflns_used    972
_cell_measurement_temperature    298(2)
_cell_measurement_theta_max      25.8290
_cell_measurement_theta_min      2.8600
_cell_volume                     1531.9(3)
_computing_cell_refinement
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET)
(compiled Feb  1 2013,16:14:44)
;
_computing_data_collection
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET)
(compiled Feb  1 2013,16:14:44)
;
_computing_data_reduction
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET)
(compiled Feb  1 2013,16:14:44)
;
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'SIR2004 (Burla et al., 2007)'
_diffrn_ambient_temperature      298(2)
_diffrn_detector_area_resol_mean 16.3291
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_details
;
#__ type_ start__ end____ width___ exp.time_
  1 omega   35.00   73.00   1.0000   70.0000
omega____ theta____ kappa____ phi______ frames
    -       18.7785  179.0000    0.0000 38

#__ type_ start__ end____ width___ exp.time_
  2 omega  -25.00   18.00   1.0000   70.0000
omega____ theta____ kappa____ phi______ frames
    -       18.7785  -99.0000 -150.0000 43

#__ type_ start__ end____ width___ exp.time_
  3 omega  -10.00   51.00   1.0000   70.0000
omega____ theta____ kappa____ phi______ frames
    -       18.7785  -99.0000   60.0000 61
;
_diffrn_measurement_device_type  'Xcalibur, Eos, Gemini'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_UB_11      0.0205454000
_diffrn_orient_matrix_UB_12      0.0002490000
_diffrn_orient_matrix_UB_13      -0.0522428000
_diffrn_orient_matrix_UB_21      0.0093907000
_diffrn_orient_matrix_UB_22      -0.0646732000
_diffrn_orient_matrix_UB_23      0.0632478000
_diffrn_orient_matrix_UB_31      -0.0083746000
_diffrn_orient_matrix_UB_32      -0.0718224000
_diffrn_orient_matrix_UB_33      -0.0572619000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0555
_diffrn_reflns_av_unetI/netI     0.1204
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       29
_diffrn_reflns_limit_h_min       -36
_diffrn_reflns_limit_k_max       5
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       6
_diffrn_reflns_limit_l_min       -8
_diffrn_reflns_number            3787
_diffrn_reflns_point_group_measured_fraction_full 0.788
_diffrn_reflns_point_group_measured_fraction_max 0.779
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         26.371
_diffrn_reflns_theta_min         2.767
_diffrn_source                   'Enhance (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    0.556
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.62814
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET)
(compiled Feb  1 2013,16:14:44)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            COLORLES
_exptl_crystal_density_diffrn    1.703
_exptl_crystal_description       PLATE
_exptl_crystal_F_000             808
_exptl_crystal_size_max          0.19
_exptl_crystal_size_mid          0.19
_exptl_crystal_size_min          0.15
_refine_diff_density_max         0.415
_refine_diff_density_min         -0.341
_refine_diff_density_rms         0.087
_refine_ls_abs_structure_details
;
 Flack x determined using 284 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.15(16)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.090
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     230
_refine_ls_number_reflns         2439
_refine_ls_number_restraints     2
_refine_ls_restrained_S_all      1.089
_refine_ls_R_factor_all          0.1302
_refine_ls_R_factor_gt           0.0805
_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)+(0.0292P)²+0.8705P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1161
_refine_ls_wR_factor_ref         0.1278
_reflns_Friedel_coverage         0.439
_reflns_Friedel_fraction_full    0.536
_reflns_Friedel_fraction_max     0.520
_reflns_number_gt                1499
_reflns_number_total             2439
_reflns_threshold_expression     'I > 2σ(I)'
_publcif_datablock.id            {2815d072-ab9a-401b-a018-5ea5da7bbc02}
_cod_data_source_file            lq5020.cif
_cod_data_source_block           HCTHPFORMII
_cod_database_code               1551862
_shelx_shelxl_version_number     2016/6
_chemical_oxdiff_formula         'C H N O S CL'
_chemical_oxdiff_usercomment     GEETHA
_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.
;
_reflns_odcompleteness_completeness 99.79
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     26.32
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups, All N(H) groups, All N(H,H) groups
2. Restrained distances
 N4-H4A
 0.85 with sigma of 0.02
3.a Secondary CH2 refined with riding coordinates:
 C7(H7A,H7B)
3.b Aromatic/amide H refined with riding coordinates:
 C1(H1), C4(H4), N1(H1A), C9(H9), C12(H12), C10(H10), C11(H11)
;
_olex2_submission_special_instructions 'No special instructions were received'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, z+1/2'
'-x+1/2, y+1/2, z+1/2'
'x+1/2, -y+1/2, 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
S2 S 0.77132(9) 0.6948(4) 0.6662(4) 0.0294(6) Uani 1 1 d .
S1 S 0.94206(9) 0.7031(4) 0.9351(4) 0.0344(7) Uani 1 1 d .
Cl1 Cl 0.81182(10) 0.8265(4) 0.2615(4) 0.0509(8) Uani 1 1 d .
C1 C 0.8589(3) 0.7092(12) 0.7702(15) 0.028(2) Uani 1 1 d .
H1 H 0.847749 0.674684 0.887538 0.033 Uiso 1 1 calc R
C4 C 0.8922(4) 0.8055(14) 0.4233(16) 0.037(3) Uani 1 1 d .
H4 H 0.902895 0.838507 0.304650 0.044 Uiso 1 1 calc R
N1 N 0.9677(3) 0.7917(12) 0.5392(12) 0.039(2) Uani 1 1 d .
H1A H 0.977058 0.811686 0.426097 0.047 Uiso 1 1 calc R
O3 O 0.7688(2) 0.6339(9) 0.8559(9) 0.0374(19) Uani 1 1 d .
C5 C 0.9225(3) 0.7783(13) 0.5673(15) 0.032(3) Uani 1 1 d .
O1 O 0.9501(2) 0.8764(10) 1.0210(10) 0.043(2) Uani 1 1 d .
O4 O 0.7543(2) 0.5826(10) 0.5183(10) 0.0391(17) Uani 1 1 d .
C2 C 0.8296(4) 0.7357(12) 0.6236(14) 0.027(3) Uani 1 1 d .
C3 C 0.8464(4) 0.7849(14) 0.4511(15) 0.032(2) Uani 1 1 d .
C7 C 1.0008(4) 0.7752(15) 0.6822(17) 0.042(3) Uani 1 1 d .
H7A H 1.005281 0.893174 0.741036 0.051 Uiso 1 1 calc R
H7B H 1.029395 0.738739 0.625748 0.051 Uiso 1 1 calc R
C6 C 0.9048(3) 0.7329(12) 0.7461(15) 0.027(2) Uani 1 1 d .
O2 O 0.9281(2) 0.5574(9) 1.0528(9) 0.0388(19) Uani 1 1 d .
N2 N 0.9882(3) 0.6430(12) 0.8270(13) 0.041(3) Uani 1 1 d .
H2 H 0.988(4) 0.538(14) 0.798(14) 0.050 Uiso 1 1 d R
N3 N 0.7438(3) 0.8795(11) 0.6559(13) 0.035(2) Uani 1 1 d .
H3A H 0.745(4) 0.948(12) 0.739(16) 0.042 Uiso 1 1 d R
H3B H 0.742(3) 0.953(13) 0.548(12) 0.042 Uiso 1 1 d R
O5 O 0.9651(2) 0.2714(10) 0.7558(12) 0.052(2) Uani 1 1 d .
C8 C 0.9253(4) 0.2609(13) 0.6994(16) 0.040(3) Uani 1 1 d .
N4 N 0.9150(5) 0.3136(16) 0.5196(17) 0.065(3) Uani 1 1 d D
C9 C 0.8895(4) 0.1947(15) 0.8020(17) 0.047(3) Uani 1 1 d .
H9 H 0.895199 0.147796 0.921571 0.056 Uiso 1 1 calc R
C12 C 0.8720(6) 0.308(2) 0.454(3) 0.088(6) Uani 1 1 d .
H12 H 0.866545 0.345914 0.331158 0.106 Uiso 1 1 calc R
C10 C 0.8465(5) 0.1946(18) 0.737(3) 0.075(5) Uani 1 1 d .
H10 H 0.822697 0.156650 0.814377 0.090 Uiso 1 1 calc R
C11 C 0.8383(6) 0.252(2) 0.554(3) 0.102(9) Uani 1 1 d .
H11 H 0.809033 0.250337 0.504209 0.122 Uiso 1 1 calc R
H4A H 0.931(8) 0.38(3) 0.45(4) 0.33(17) Uiso 1 1 d 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'
S S 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cl Cl 0.1484 0.1585 '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 S2 O4 119.8(4)
O3 S2 C2 105.4(5)
O3 S2 N3 106.7(5)
O4 S2 C2 108.3(5)
O4 S2 N3 106.4(5)
N3 S2 C2 110.1(5)
O1 S1 C6 108.6(4)
O1 S1 N2 107.7(5)
O2 S1 O1 117.9(4)
O2 S1 C6 111.3(4)
O2 S1 N2 108.4(5)
N2 S1 C6 101.4(5)
C2 C1 H1 119.7
C2 C1 C6 120.7(10)
C6 C1 H1 119.7
C5 C4 H4 119.4
C5 C4 C3 121.2(10)
C3 C4 H4 119.4
C5 N1 H1A 117.7
C5 N1 C7 124.6(9)
C7 N1 H1A 117.7
C4 C5 C6 117.5(9)
N1 C5 C4 121.5(10)
N1 C5 C6 121.0(10)
C1 C2 S2 117.4(7)
C1 C2 C3 119.2(10)
C3 C2 S2 123.3(8)
C4 C3 Cl1 116.9(9)
C2 C3 Cl1 122.2(8)
C2 C3 C4 120.9(11)
N1 C7 H7A 109.0
N1 C7 H7B 109.0
N1 C7 N2 112.8(9)
H7A C7 H7B 107.8
N2 C7 H7A 109.0
N2 C7 H7B 109.0
C1 C6 S1 120.5(9)
C1 C6 C5 120.4(10)
C5 C6 S1 119.1(7)
S1 N2 H2 112(8)
C7 N2 S1 111.3(7)
C7 N2 H2 118(8)
S2 N3 H3A 120(8)
S2 N3 H3B 124(6)
H3A N3 H3B 104(9)
O5 C8 N4 119.5(12)
O5 C8 C9 125.3(11)
N4 C8 C9 115.2(12)
C8 N4 H4A 126(10)
C12 N4 C8 121.3(15)
C12 N4 H4A 110(10)
C8 C9 H9 118.5
C10 C9 C8 122.9(13)
C10 C9 H9 118.5
N4 C12 H12 118.4
C11 C12 N4 123.1(18)
C11 C12 H12 118.4
C9 C10 H10 120.6
C9 C10 C11 118.8(16)
C11 C10 H10 120.6
C12 C11 C10 118.5(15)
C12 C11 H11 120.8
C10 C11 H11 120.8
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
S2 O3 1.419(6)
S2 O4 1.424(7)
S2 C2 1.768(11)
S2 N3 1.582(8)
S1 O1 1.430(7)
S1 C6 1.745(10)
S1 O2 1.418(7)
S1 N2 1.622(10)
Cl1 C3 1.713(11)
C1 H1 0.9300
C1 C2 1.365(13)
C1 C6 1.372(12)
C4 H4 0.9300
C4 C5 1.370(14)
C4 C3 1.372(14)
N1 H1A 0.8600
N1 C5 1.349(12)
N1 C7 1.410(13)
C5 C6 1.410(13)
C2 C3 1.367(14)
C7 H7A 0.9700
C7 H7B 0.9700
C7 N2 1.460(13)
N2 H2 0.80(10)
N3 H3A 0.77(10)
N3 H3B 0.94(9)
O5 C8 1.242(12)
C8 N4 1.366(15)
C8 C9 1.368(15)
N4 C12 1.347(19)
N4 H4A 0.85(3)
C9 H9 0.9300
C9 C10 1.348(17)
C12 H12 0.9300
C12 C11 1.29(2)
C10 H10 0.9300
C10 C11 1.39(2)
C11 H11 0.9300
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 PubChem 168303059
