Mebendazolium mesylate anhydride salt: rational design based on supramolecular assembly, synthesis, and solid-state characterization
Gutiérrez, Eduardo L.; Godoy, Agustín A.; Brusau, Elena V.; Vega, Daniel; Narda, Griselda E.; Suárez, Sebastián; Di Salvo, Florencia; RSC Advances 14 (2024) 181–192; doi:10.1039/D3RA07422F

data_7247939
_publ_section_title
;
 Mebendazolium mesylate anhydride salt: rational design based on
 supramolecular assembly, synthesis, and solid-state characterization
;
_journal_issue                   1
_journal_name_full               'RSC Advances'
_journal_page_first              181
_journal_page_last               192
_journal_paper_doi               10.1039/D3RA07422F
_journal_volume                  14
_journal_year                    2024
_chemical_absolute_configuration rm
_chemical_formula_moiety         'C16 H14 N3 O3, C H3 O3 S'
_chemical_formula_sum            'C17 H17 N3 O6 S'
_chemical_formula_weight         391.39
_chemical_name_systematic        'Mebendazolium mesylate anhydride salt'
_space_group_crystal_system      orthorhombic
_space_group_IT_number           19
_space_group_name_Hall           'P 2ac 2ab'
_space_group_name_H-M_alt        'P 21 21 21'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_audit_creation_date             2023-10-19
_audit_creation_method
;
Olex2 1.5
(compiled 2023.08.24 svn.re1ec1418 for OlexSys, GUI svn.r6817)
;
_audit_update_record
;
2023-10-23 deposited with the CCDC.	2023-12-08 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   7.2177(3)
_cell_length_b                   9.2009(4)
_cell_length_c                   27.0007(17)
_cell_measurement_reflns_used    2765
_cell_measurement_temperature    293
_cell_measurement_theta_max      72.1140
_cell_measurement_theta_min      4.7940
_cell_volume                     1793.10(16)
_computing_cell_refinement       'CrysAlisPro 1.171.41.95a (Rigaku OD, 2021)'
_computing_data_collection       'CrysAlisPro 1.171.41.95a (Rigaku OD, 2021)'
_computing_data_reduction        'CrysAlisPro 1.171.41.95a (Rigaku OD, 2021)'
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2019/2 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXS  (Sheldrick, 2008)'
_diffrn_ambient_temperature      293
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 16.1158
_diffrn_detector_type            Eos
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measurement_details
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  t~exp~   \w     \q     \k     \f   Frames
  1  \w    -12.00  13.00   1.00   13.57    --    0.00  98.00  20.00   25
  2  \w    -78.00 -23.00   1.00   55.52    --  -59.32  98.00  20.00   55
  3  \w   -133.00 -84.00   1.00   55.52    --  -59.32 -98.00 -87.00   49
  4  \w      1.00  55.00   1.00   55.52    --   59.32 -98.00 -87.00   54
  5  \w     74.00  99.00   1.00  156.51    --  116.00 -98.00 -87.00   25
  6  \w    112.00 138.00   1.00  156.51    --  116.00  98.00  20.00   26
  7  \w    -69.00 -38.00   1.00   13.57    --    0.00 178.00 120.00   31
  8  \w    -82.00 -37.00   1.00   13.57    --    0.00 178.00 -30.00   45
  9  \w   -121.00 -76.00   1.00   55.52    --  -59.32-125.00   0.00   45
 10  \w   -131.00 -93.00   1.00   55.52    --  -59.32 -94.00-150.00   38
 11  \w   -123.00 -84.00   1.00   55.52    --  -59.32 -94.00  60.00   39
 12  \w   -133.00 -84.00   1.00   55.52    --  -59.32 -94.00 150.00   49
 13  \w    147.00 176.00   1.00  156.51    --  116.00  77.00-120.00   29
 14  \w     43.00 106.00   1.00  156.51    --  116.00 -91.00-150.00   63
 15  \w     63.00 107.00   1.00  156.51    --  116.00 -63.00 -90.00   44
 16  \w     48.00  95.00   1.00  156.51    --  116.00 -91.00 -30.00   47
 17  \w    131.00 165.00   1.00  156.51    --  116.00  63.00 150.00   34
 18  \w    102.00 135.00   1.00  156.51    --  116.00  77.00-120.00   33
 19  \w    100.00 127.00   1.00  156.51    --  116.00 -77.00 -90.00   27
 20  \w    104.00 162.00   1.00  156.51    --  116.00  77.00-180.00   58
 21  \w     47.00  74.00   1.00  156.51    --  116.00 -77.00 -90.00   27
 22  \w    103.00 130.00   1.00  156.51    --  116.00  37.00 150.00   27
 23  \w    135.00 175.00   1.00  156.51    --  116.00 111.00 -60.00   40
 24  \w    112.00 178.00   1.00  156.51    --  116.00 111.00 -90.00   66
 25  \w     44.00  90.00   1.00  156.51    --  116.00 -91.00  90.00   46
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'Xcalibur, Eos, Gemini'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.1286180000
_diffrn_orient_matrix_UB_12      -0.0186354000
_diffrn_orient_matrix_UB_13      0.0451612000
_diffrn_orient_matrix_UB_21      0.1199099000
_diffrn_orient_matrix_UB_22      -0.1079450000
_diffrn_orient_matrix_UB_23      -0.0295445000
_diffrn_orient_matrix_UB_31      0.1209290000
_diffrn_orient_matrix_UB_32      0.1265543000
_diffrn_orient_matrix_UB_33      -0.0186179000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0440
_diffrn_reflns_av_unetI/netI     0.0547
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.996
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       33
_diffrn_reflns_limit_l_min       -33
_diffrn_reflns_number            6778
_diffrn_reflns_point_group_measured_fraction_full 0.929
_diffrn_reflns_point_group_measured_fraction_max 0.914
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         73.631
_diffrn_reflns_theta_min         5.078
_diffrn_source                   'fine-focus sealed X-ray tube'
_diffrn_source_type              'Enhance (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    1.975
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.64360
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.41.95a (Rigaku Oxford Diffraction, 2021)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            'clear whiteish colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   whiteish
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.450
_exptl_crystal_description       block
_exptl_crystal_F_000             816
_exptl_crystal_recrystallization_method
'Re-crystallisation from solvent: methanol'
_exptl_crystal_size_max          0.3
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.1
_refine_diff_density_max         0.294
_refine_diff_density_min         -0.411
_refine_diff_density_rms         0.063
_refine_ls_abs_structure_details
;
 Flack x determined using 822 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.12(4)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.123
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     246
_refine_ls_number_reflns         3311
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.123
_refine_ls_R_factor_all          0.0773
_refine_ls_R_factor_gt           0.0628
_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^)+(0.0622P)^2^+1.9502P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1717
_refine_ls_wR_factor_ref         0.1814
_reflns_Friedel_coverage         0.577
_reflns_Friedel_fraction_full    0.833
_reflns_Friedel_fraction_max     0.799
_reflns_number_gt                2774
_reflns_number_total             3311
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d3ra07422f2.cif
_cod_data_source_block           MBZH-MsO
_cod_original_cell_volume        1793.09(16)
_cod_database_code               7247939
_shelx_shelxl_version_number     2019/2
_olex2_refinement_description
;
1.a Aromatic/amide H refined with riding coordinates:
 N1(H1), N2(H2), N3(H3), C6(H6), C7(H7), C9(H9), C12(H12), C13(H13), C14(H14),
 C15(H15), C16(H16)
1.b Idealised Me refined as rotating group:
 C1(H1A,H1B,H1C), C17(H17A,H17B,H17C)
;
_shelx_res_checksum              21955
_shelx_hkl_checksum              84539
_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 1.481
_oxdiff_exptl_absorpt_empirical_full_min 0.456