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_1551855
_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         'C17 H14 F3 N3 O2 S, C6 H7 N O'
_chemical_formula_sum            'C23 H21 F3 N4 O3 S'
_chemical_formula_weight         490.50
_chemical_melting_point          388
_chemical_name_common            CELMeHP
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -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                113.451(10)
_cell_angle_beta                 100.897(8)
_cell_angle_gamma                101.744(7)
_cell_formula_units_Z            2
_cell_length_a                   10.0694(8)
_cell_length_b                   10.6113(10)
_cell_length_c                   12.6499(14)
_cell_measurement_reflns_used    1937
_cell_measurement_temperature    298(2)
_cell_measurement_theta_max      27.1570
_cell_measurement_theta_min      3.1490
_cell_volume                     1157.9(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 0.999
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_details
;
  1 omega  -53.00   45.00   1.0000   53.0000
omega____ theta____ kappa____ phi______ frames
    -       18.7785  -37.0000 -180.0000 98

  2 omega    4.00   80.00   1.0000   53.0000
omega____ theta____ kappa____ phi______ frames
    -       18.7785   57.0000   90.0000 76

  3 omega   -5.00   84.00   1.0000   53.0000
omega____ theta____ kappa____ phi______ frames
    -       18.7785   37.0000    0.0000 89

  4 omega   36.00   79.00   1.0000   53.0000
omega____ theta____ kappa____ phi______ frames
    -       18.7785  179.0000 -150.0000 43

  5 omega  -19.00   13.00   1.0000   53.0000
omega____ theta____ kappa____ phi______ frames
    -      -19.0128  -99.0000  -30.0000 32

  6 omega  -25.00   20.00   1.0000   53.0000
omega____ theta____ kappa____ phi______ frames
    -      -19.0128  -99.0000  150.0000 45
;
_diffrn_measurement_device_type  'Xcalibur, Eos, Gemini'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_UB_11      0.0542540000
_diffrn_orient_matrix_UB_12      0.0674592000
_diffrn_orient_matrix_UB_13      0.0342965000
_diffrn_orient_matrix_UB_21      -0.0199334000
_diffrn_orient_matrix_UB_22      0.0198267000
_diffrn_orient_matrix_UB_23      -0.0465936000
_diffrn_orient_matrix_UB_31      -0.0484758000
_diffrn_orient_matrix_UB_32      0.0304498000
_diffrn_orient_matrix_UB_33      0.0275611000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0260
_diffrn_reflns_av_unetI/netI     0.0538
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            8277
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         26.371
_diffrn_reflns_theta_min         2.948
_diffrn_source                   'Enhance (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    0.197
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.84503
_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    1.407
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       PLATE
_exptl_crystal_F_000             508
_exptl_crystal_size_max          0.24
_exptl_crystal_size_mid          0.22
_exptl_crystal_size_min          0.20
_refine_diff_density_max         0.818
_refine_diff_density_min         -0.359
_refine_diff_density_rms         0.059
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.033
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     315
_refine_ls_number_reflns         4717
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.033
_refine_ls_R_factor_all          0.1030
_refine_ls_R_factor_gt           0.0675
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.1023P)^2^+0.4128P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1780
_refine_ls_wR_factor_ref         0.2048
_reflns_Friedel_coverage         0.000
_reflns_number_gt                3080
_reflns_number_total             4717
_reflns_threshold_expression     'I > 2\s(I)'
_publcif_datablock.id            {2677737d-c1d1-4a27-93f2-3ff084cde64f}
_cod_data_source_file            lq5020.cif
_cod_data_source_block           CELMeHP
_cod_database_code               1551855
_shelx_shelxl_version_number     2016/6
_chemical_oxdiff_formula         'C H N O S F'
_chemical_oxdiff_usercomment     Geetha
_reflns_odcompleteness_completeness 99.83
_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 N(H) groups, All N(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C5(H5), C12(H12), C4(H4), C18(H18), C19(H19), C21(H21), C25(H25), C27(H27),
 C28(H28), N1(H1), C29(H29), C31(H31), C33(H33)
2.b Idealised Me refined as rotating group:
 C32(H32A,H32B,H32C), C30(H30A,H30B,H30C)
;
_shelx_res_checksum              10726
_shelx_hkl_checksum              61282
_olex2_submission_special_instructions 'No special instructions were received'