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_1551862
_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          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
;
  1 omega   35.00   73.00   1.0000   70.0000
omega____ theta____ kappa____ phi______ frames
    -       18.7785  179.0000    0.0000 38

  2 omega  -25.00   18.00   1.0000   70.0000
omega____ theta____ kappa____ phi______ frames
    -       18.7785  -99.0000 -150.0000 43

  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       '\w 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/[\s^2^(Fo^2^)+(0.0292P)^2^+0.8705P] where P=(Fo^2^+2Fc^2^)/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 > 2\s(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
_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)
;
_shelx_res_checksum              43139
_shelx_hkl_checksum              46807
_olex2_submission_special_instructions 'No special instructions were received'