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_1551858
_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         'C12 H11 Cl N2 O5 S, 0.5(C2 H6 O), C4 H7 N O'
_chemical_formula_sum            'C17 H21 Cl N3 O6.5 S'
_chemical_formula_weight         439.38
_chemical_melting_point          383
_chemical_name_common            FUROS2PY
_space_group_crystal_system      monoclinic
_space_group_IT_number           15
_space_group_name_Hall           '-C 2yc'
_space_group_name_H-M_alt        'C 1 2/c 1'
_symmetry_space_group_name_Hall  '-C 2yc'
_symmetry_space_group_name_H-M   'C 1 2/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                 123.868(16)
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   23.819(3)
_cell_length_b                   8.4372(5)
_cell_length_c                   23.450(2)
_cell_measurement_reflns_used    3313
_cell_measurement_temperature    298(2)
_cell_measurement_theta_max      28.1720
_cell_measurement_theta_min      3.4250
_cell_volume                     3913.0(10)
_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      293(2)
_diffrn_detector_area_resol_mean 16.3291
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_details
;
  1 omega   19.00   91.00   1.0000   53.0000
omega____ theta____ kappa____ phi______ frames
    -       18.9347   37.0000  150.0000 72

  2 omega   45.00   71.00   1.0000   53.0000
omega____ theta____ kappa____ phi______ frames
    -       18.9347  179.0000    0.0000 26

  3 omega  -13.00   89.00   1.0000   53.0000
omega____ theta____ kappa____ phi______ frames
    -       18.9347   19.0000   90.0000 102

  4 omega  -18.00   21.00   1.0000   53.0000
omega____ theta____ kappa____ phi______ frames
    -      -19.1691  -99.0000   30.0000 39
;
_diffrn_measurement_device_type  'Xcalibur, Eos, Gemini'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_UB_11      0.0179915000
_diffrn_orient_matrix_UB_12      0.0209658000
_diffrn_orient_matrix_UB_13      -0.0148757000
_diffrn_orient_matrix_UB_21      -0.0306719000
_diffrn_orient_matrix_UB_22      -0.0005533000
_diffrn_orient_matrix_UB_23      -0.0330722000
_diffrn_orient_matrix_UB_31      -0.0048449000
_diffrn_orient_matrix_UB_32      0.0813429000
_diffrn_orient_matrix_UB_33      0.0036121000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0239
_diffrn_reflns_av_unetI/netI     0.0303
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_limit_h_max       28
_diffrn_reflns_limit_h_min       -28
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       27
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            7270
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_theta_full        24.710
_diffrn_reflns_theta_max         24.710
_diffrn_reflns_theta_min         2.978
_diffrn_source                   'Enhance (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    0.345
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.80170
_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    1.492
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       BLOCK
_exptl_crystal_F_000             1836
_exptl_crystal_size_max          0.25
_exptl_crystal_size_mid          0.22
_exptl_crystal_size_min          0.20
_refine_diff_density_max         0.414
_refine_diff_density_min         -0.532
_refine_diff_density_rms         0.086
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.058
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     274
_refine_ls_number_reflns         3327
_refine_ls_number_restraints     3
_refine_ls_restrained_S_all      1.058
_refine_ls_R_factor_all          0.0726
_refine_ls_R_factor_gt           0.0596
_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^)+(0.0917P)^2^+5.9596P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1601
_refine_ls_wR_factor_ref         0.1718
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2676
_reflns_number_total             3327
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            lq5020.cif
_cod_data_source_block           FUROS2PY
_cod_depositor_comments
;

2022-09-15
Z value and formula fixed to values more according to usual
chemical conventions.                 miguel
;
_cod_original_formula_sum            'C34 H43 Cl2 N6 O13 S2'
_cod_original_formula_weight         878.76
_cod_original_formula_moiety
'2(C12 H11 Cl N2 O5 S), C2 H7 O, 2(C4 H7 N O)'
_cod_original_formula_units_Z            4
_cod_original_cell_volume        3913.0(9)
_cod_database_code               1551858
_publcif_datablock.id            {d13c21dc-338a-43e4-b242-c21ab5e529fa}
_shelx_shelxl_version_number     2016/6
_chemical_oxdiff_formula         'C H N O S'
_chemical_oxdiff_usercomment     GEETHA
_reflns_odcompleteness_completeness 99.75
_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 C(H,H) groups, All N(H) groups
 At 1.5 times of:
  All C(H,H,H) groups, All O(H) groups
2. Restrained distances
 O7-H7
 0.9 with sigma of 0.02
 N1-H1A
 0.9 with sigma of 0.02
 N1-H1B
 0.9 with sigma of 0.02
3.a Secondary CH2 refined with riding coordinates:
 C8(H8A,H8B), C14(H14A,H14B), C16(H16A,H16B), C15(H15A,H15B)
3.b Aromatic/amide H refined with riding coordinates:
 C3(H3), N2(H2), C6(H6), C10(H10), C12(H12), C11(H11)
3.c Idealised Me refined as rotating group:
 C17(H17A,H17B,H17C)
3.d Idealised tetrahedral OH refined as rotating group:
 O4(H4)
;
_shelx_res_checksum              28528
_shelx_hkl_checksum              20324
_olex2_submission_special_instructions 'No special instructions were received'