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_1551854
_publ_section_title
;
 Supramolecular synthon hierarchy in sulfonamide cocrystals with
 <i>syn</i>-amides and <i>N</i>-oxides
;
_journal_coeditor_code           LQ5020
_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, C5 H5 N O'
_chemical_formula_sum            'C22 H19 F3 N4 O3 S'
_chemical_formula_weight         476.47
_chemical_melting_point          383
_chemical_name_common            CEL2HP
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2yn'
_space_group_name_H-M_alt        'P 1 21/n 1'
_symmetry_space_group_name_Hall  '-P 2yn'
_symmetry_space_group_name_H-M   'P 1 21/n 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)
;
_audit_update_record
;
2017-07-07 # Formatted by publCIF

;
_cell_angle_alpha                90
_cell_angle_beta                 93.899(9)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   14.5182(15)
_cell_length_b                   8.2844(12)
_cell_length_c                   17.8349(18)
_cell_measurement_reflns_used    2029
_cell_measurement_temperature    298(2)
_cell_measurement_theta_max      24.4740
_cell_measurement_theta_min      3.0450
_cell_volume                     2140.1(4)
_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  -18.00   88.00   1.0000   50.0000
omega____ theta____ kappa____ phi______ frames
    -       18.7785   19.0000  -90.0000 106

  2 omega  -44.00   38.00   1.0000   50.0000
omega____ theta____ kappa____ phi______ frames
    -       18.7785  -57.0000   90.0000 82

  3 omega   -2.00   82.00   1.0000   50.0000
omega____ theta____ kappa____ phi______ frames
    -       18.7785   57.0000  -30.0000 84

  4 omega   50.00   76.00   1.0000   50.0000
omega____ theta____ kappa____ phi______ frames
    -       18.7785  179.0000  120.0000 26

  5 omega  -25.00   23.00   1.0000   50.0000
omega____ theta____ kappa____ phi______ frames
    -      -19.0128  -99.0000    0.0000 48

  6 omega  -25.00   21.00   1.0000   50.0000
omega____ theta____ kappa____ phi______ frames
    -      -19.0128  -99.0000 -180.0000 46
;
_diffrn_measurement_device_type  'Xcalibur, Eos, Gemini'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_UB_11      -0.0045541000
_diffrn_orient_matrix_UB_12      -0.0471337000
_diffrn_orient_matrix_UB_13      0.0327354000
_diffrn_orient_matrix_UB_21      0.0487802000
_diffrn_orient_matrix_UB_22      -0.0070519000
_diffrn_orient_matrix_UB_23      0.0049622000
_diffrn_orient_matrix_UB_31      0.0017684000
_diffrn_orient_matrix_UB_32      0.0709522000
_diffrn_orient_matrix_UB_33      0.0222396000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0671
_diffrn_reflns_av_unetI/netI     0.0828
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       17
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_number            12941
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_theta_full        24.708
_diffrn_reflns_theta_max         24.708
_diffrn_reflns_theta_min         2.712
_diffrn_source                   'Enhance (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    0.211
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.82495
_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    1.479
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       BLOCK
_exptl_crystal_F_000             984
_exptl_crystal_size_max          0.24
_exptl_crystal_size_mid          0.21
_exptl_crystal_size_min          0.20
_refine_diff_density_max         0.239
_refine_diff_density_min         -0.296
_refine_diff_density_rms         0.048
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.987
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     305
_refine_ls_number_reflns         3634
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.987
_refine_ls_R_factor_all          0.0968
_refine_ls_R_factor_gt           0.0494
_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^)+(0.0299P)^2^] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0891
_refine_ls_wR_factor_ref         0.1082
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2269
_reflns_number_total             3634
_reflns_threshold_expression     'I > 2\s(I)'
_publcif_datablock.id            {e6e66f9a-2d9c-4520-a5e5-afc88f9dafd0}
_cod_data_source_file            lq5020.cif
_cod_data_source_block           CEL2HP
_cod_database_code               1551854
_shelx_shelxl_version_number     2016/6
_chemical_oxdiff_formula         'C H N O S F'
_chemical_oxdiff_usercomment     CHP
_reflns_odcompleteness_completeness 99.77
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     24.66
_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:
 C16(H16), C2(H2), C13(H13), C17(H17), C10(H10), C14(H14), C6(H6), C9(H9),
 C7(H7), N4(H4), C19(H19), C22(H22), C20(H20), C21(H21)
2.b Idealised Me refined as rotating group:
 C11(H11A,H11B,H11C)
;
_shelx_res_checksum              24221
_shelx_hkl_checksum              30677
_olex2_submission_special_instructions 'No special instructions were received'