Supramolecular synthon hierarchy in sulfonamide cocrystals with <i>syn</i>-amides and <i>N</i>-oxides
Bolla, Geetha; Nangia, Ashwini; IUCrJ 6 (2019) –; doi:10.1107/S2052252519005037

data_1551861
_publ_section_title
;
 Supramolecular synthon hierarchy in sulfonamide cocrystals with
 <i>syn</i>-amides and <i>N</i>-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          417
_chemical_name_common            HCT2HPFORMI
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2ybc'
_space_group_name_H-M_alt        'P 1 21/c 1'
_symmetry_space_group_name_Hall  '-P 2ybc'
_symmetry_space_group_name_H-M   'P 1 21/c 1'
_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                 113.113(9)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   6.8039(5)
_cell_length_b                   13.5399(8)
_cell_length_c                   18.8949(13)
_cell_measurement_reflns_used    2169
_cell_measurement_temperature    298(2)
_cell_measurement_theta_max      71.7220
_cell_measurement_theta_min      3.2640
_cell_volume                     1601.0(2)
_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 1.000
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measurement_details
;
  1 omega   -4.00   21.00   1.0000   15.0000
omega____ theta____ kappa____ phi______ frames
    -        0.0000  -99.0000  150.0000 25

  2 omega    9.00   35.00   1.0000   15.0000
omega____ theta____ kappa____ phi______ frames
    -        0.0000   57.0000  120.0000 26

  3 omega  -77.00   14.00   1.0000   15.0000
omega____ theta____ kappa____ phi______ frames
    -      -42.5000  111.0000   30.0000 91

  4 omega -106.00  -24.00   1.0000   15.0000
omega____ theta____ kappa____ phi______ frames
    -      -42.5000  -57.0000  -60.0000 82

  5 omega   -9.00   17.00   1.0000   15.0000
omega____ theta____ kappa____ phi______ frames
    -      -42.5000   37.0000 -180.0000 26

  6 omega -115.00  -59.00   1.0000   15.0000
omega____ theta____ kappa____ phi______ frames
    -      -42.5000  -37.0000    0.0000 56

  7 omega   33.00   80.00   1.0000   15.0000
omega____ theta____ kappa____ phi______ frames
    -       54.8467  -77.0000 -150.0000 47

  8 omega   55.00   93.00   1.0000   14.0000
omega____ theta____ kappa____ phi______ frames
    -      109.6934  -25.0000    0.0000 38

  9 omega   39.00   78.00   1.0000   14.0000
omega____ theta____ kappa____ phi______ frames
    -      109.6934  -37.0000  120.0000 39

 10 omega   39.00   92.00   1.0000   14.0000
omega____ theta____ kappa____ phi______ frames
    -      109.6934  -37.0000  -90.0000 53

 11 omega   42.00  129.00   1.0000   14.0000
omega____ theta____ kappa____ phi______ frames
    -      109.6934  -77.0000  -30.0000 87

 12 omega   84.00  159.00   1.0000   14.0000
omega____ theta____ kappa____ phi______ frames
    -      109.6934   37.0000 -120.0000 75

 13 omega   38.00   89.00   1.0000   14.0000
omega____ theta____ kappa____ phi______ frames
    -      109.6934  -37.0000  -30.0000 51

 14 omega   44.00  113.00   1.0000   14.0000
omega____ theta____ kappa____ phi______ frames
    -      109.6934 -111.0000  -30.0000 69

 15 omega   38.00   90.00   1.0000   14.0000
omega____ theta____ kappa____ phi______ frames
    -      109.6934  -25.0000 -150.0000 52

 16 omega   62.00   88.00   1.0000   14.0000
omega____ theta____ kappa____ phi______ frames
    -      109.6934  -25.0000   60.0000 26
;
_diffrn_measurement_device_type  'Xcalibur, Eos, Gemini'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_UB_11      0.0260864000
_diffrn_orient_matrix_UB_12      0.1105702000
_diffrn_orient_matrix_UB_13      -0.0134630000
_diffrn_orient_matrix_UB_21      0.0850837000
_diffrn_orient_matrix_UB_22      0.0184972000
_diffrn_orient_matrix_UB_23      0.0873738000
_diffrn_orient_matrix_UB_31      0.2296154000
_diffrn_orient_matrix_UB_32      -0.0194682000
_diffrn_orient_matrix_UB_33      0.0065369000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0239
_diffrn_reflns_av_unetI/netI     0.0354
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -5
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_number            5295
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 1.000
_diffrn_reflns_theta_full        67.064
_diffrn_reflns_theta_max         67.064
_diffrn_reflns_theta_min         4.139
_diffrn_source                   'Enhance (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    4.867
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.62290
_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    1.630
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       PLATE
_exptl_crystal_F_000             808
_exptl_crystal_size_max          0.24
_exptl_crystal_size_mid          0.22
_exptl_crystal_size_min          0.21
_refine_diff_density_max         0.937
_refine_diff_density_min         -0.416
_refine_diff_density_rms         0.108
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.155
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     226
_refine_ls_number_reflns         2853
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.155
_refine_ls_R_factor_all          0.0790
_refine_ls_R_factor_gt           0.0717
_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/[\s^2^(Fo^2^)+(0.0776P)^2^+5.6938P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1946
_refine_ls_wR_factor_ref         0.1991
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2452
_reflns_number_total             2853
_reflns_threshold_expression     'I > 2\s(I)'
_publcif_datablock.id            {d6af9464-a43b-41c3-acb2-cacf525e3008}
_cod_data_source_file            lq5020.cif
_cod_data_source_block           HCT2HPFORMI
_cod_database_code               1551861
_shelx_shelxl_version_number     2016/6
_chemical_oxdiff_formula         'C H N O S CL'
_chemical_oxdiff_usercomment     GEETHA
_reflns_odcompleteness_completeness 99.93
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.97
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups, All N(H) groups
 At 1.5 times of:
  All N(H,H) groups
2.a Secondary CH2 refined with riding coordinates:
 C7(H7A,H7B)
2.b Aromatic/amide H refined with riding coordinates:
 N1(H1), C1(H1A), N4(H4A), C4(H4), C10(H10), C9(H9), C12(H12), C11(H11)
;
_shelx_res_checksum              19651
_shelx_hkl_checksum              25119
_olex2_submission_special_instructions 'No special instructions were received'