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_1551860
_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, C5 H9 N O, H2 O'
_chemical_formula_sum            'C17 H22 Cl N3 O7 S'
_chemical_formula_weight         447.88
_chemical_melting_point          371
_chemical_name_common            FUROSVLM
_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)
;
_cell_angle_alpha                90
_cell_angle_beta                 93.12(3)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   11.116(5)
_cell_length_b                   8.447(2)
_cell_length_c                   21.388(7)
_cell_measurement_reflns_used    1013
_cell_measurement_temperature    298(2)
_cell_measurement_theta_max      20.0240
_cell_measurement_theta_min      3.0440
_cell_volume                     2005.3(12)
_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 0.997
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_details
;
  1 omega  -36.00   62.00   1.0000   63.0000
omega____ theta____ kappa____ phi______ frames
    -       18.7785  -19.0000  120.0000 98

  2 omega  -34.00   25.00   1.0000   63.0000
omega____ theta____ kappa____ phi______ frames
    -       18.7785  -57.0000   60.0000 59

  3 omega   64.00   92.00   1.0000   63.0000
omega____ theta____ kappa____ phi______ frames
    -       18.7785  174.0000    9.0000 28

  4 omega  -45.00  -13.00   1.0000   63.0000
omega____ theta____ kappa____ phi______ frames
    -       18.7785  -57.0000  -60.0000 32

  5 omega  -12.00   18.00   1.0000   63.0000
omega____ theta____ kappa____ phi______ frames
    -      -19.0128  -99.0000  -90.0000 30
;
_diffrn_measurement_device_type  'Xcalibur, Eos, Gemini'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_UB_11      -0.0036217000
_diffrn_orient_matrix_UB_12      -0.0111448000
_diffrn_orient_matrix_UB_13      0.0327435000
_diffrn_orient_matrix_UB_21      0.0626029000
_diffrn_orient_matrix_UB_22      -0.0161882000
_diffrn_orient_matrix_UB_23      0.0027429000
_diffrn_orient_matrix_UB_31      0.0119327000
_diffrn_orient_matrix_UB_32      0.0816347000
_diffrn_orient_matrix_UB_33      0.0050719000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0737
_diffrn_reflns_av_unetI/netI     0.1156
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_limit_l_min       -25
_diffrn_reflns_number            7859
_diffrn_reflns_point_group_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_theta_full        24.713
_diffrn_reflns_theta_max         24.713
_diffrn_reflns_theta_min         3.030
_diffrn_source                   'Enhance (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    0.340
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.94875
_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    1.483
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       PLATE
_exptl_crystal_F_000             936
_exptl_crystal_size_max          0.22
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.20
_refine_diff_density_max         0.256
_refine_diff_density_min         -0.294
_refine_diff_density_rms         0.052
_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     275
_refine_ls_number_reflns         3402
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.987
_refine_ls_R_factor_all          0.1472
_refine_ls_R_factor_gt           0.0650
_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^)+(0.0179P)^2^] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0875
_refine_ls_wR_factor_ref         0.1141
_reflns_Friedel_coverage         0.000
_reflns_number_gt                1676
_reflns_number_total             3402
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            lq5020.cif
_cod_data_source_block           FUROSVLM
_cod_original_cell_volume        2005.4(12)
_cod_database_code               1551860
_publcif_datablock.id            {9e8a0ef0-2512-4deb-95ac-e76781e7e617}
_shelx_shelxl_version_number     2016/6
_chemical_oxdiff_formula         'C H N O S Cl'
_chemical_oxdiff_usercomment     GEETHA
_reflns_odcompleteness_completeness 99.62
_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, All N(H,H) groups
 At 1.5 times of:
  All O(H,H) groups
2.a Free rotating group:
 O7(H7A,H7B)
2.b Secondary CH2 refined with riding coordinates:
 C8(H8A,H8B), C14(H14A,H14B), C17(H17A,H17B), C15(H15A,H15B), C16(H16A,H16B)
2.c Aromatic/amide H refined with riding coordinates:
 N2(H2), C3(H3), N3(H3A), C6(H6), C11(H11), C10(H10), C12(H12)
;
_shelx_res_checksum              3493
_shelx_hkl_checksum              16192
_olex2_submission_special_instructions 'No special instructions were received'