Rational design, supramolecular synthesis and solid state characterization of two bicomponent solid forms of Mebendazole
Gutiérrez, Eduardo L. L.; Godoy, Agustin Alejandro; Narda, Griselda E.; Ellena, Javier A.; CrystEngComm  (2020) –; doi:10.1039/D0CE00924E

data_7241105
_publ_section_title
;
 Rational design, supramolecular synthesis and solid state
 characterization of two bicomponent solid forms of Mebendazole
;
_journal_name_full               CrystEngComm
_journal_paper_doi               10.1039/D0CE00924E
_journal_year                    2020
_chemical_formula_moiety         'C H3 O4 S, C16 H14 N3 O3'
_chemical_formula_sum            'C17 H17 N3 O7 S'
_chemical_formula_weight         407.39
_chemical_name_common            'Mebendazole methylbisulfate'
_chemical_name_systematic        'Mebendazole methylsulfate'
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_audit_creation_date             2019-05-02
_audit_creation_method
;
Olex2 1.2-ac3
(compiled 2017.08.10 svn.r3458 for OlexSys, GUI svn.r5381)
;
_audit_update_record
;
2020-04-08 deposited with the CCDC.	2020-08-21 downloaded from the CCDC.
;
_cell_angle_alpha                92.075(12)
_cell_angle_beta                 102.401(11)
_cell_angle_gamma                90.209(10)
_cell_formula_units_Z            2
_cell_length_a                   9.1092(11)
_cell_length_b                   9.9717(14)
_cell_length_c                   9.9908(14)
_cell_measurement_reflns_used    1318
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      32.5340
_cell_measurement_theta_min      2.9600
_cell_volume                     885.7(2)
_computing_cell_refinement       'CrysAlisPro 1.171.39.35c (Rigaku OD, 2017)'
_computing_data_collection       'CrysAlisPro 1.171.39.35c (Rigaku OD, 2017)'
_computing_data_reduction        'CrysAlisPro 1.171.39.35c (Rigaku OD, 2017)'
_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    'ShelXT (Sheldrick, 2015)'
_diffrn_ambient_temperature      293(2)
_diffrn_detector                 'CCD plate'
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.837
_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      9.00  37.00   1.00  300.00    --   27.63  54.00-150.00   28
  2  \w    -69.00 -39.00   1.00  300.00    --   27.63  54.00 -60.00   30
  3  \w     41.00 113.00   1.00  300.00    --   27.63  54.00 -60.00   72
  4  \w    -69.00 113.00   1.00  300.00    --   27.63  54.00  90.00  182
;
_diffrn_measurement_device       'two-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB Mini (ROW)'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0211285000
_diffrn_orient_matrix_UB_12      -0.0672579000
_diffrn_orient_matrix_UB_13      0.0142127000
_diffrn_orient_matrix_UB_21      0.0231230000
_diffrn_orient_matrix_UB_22      -0.0065819000
_diffrn_orient_matrix_UB_23      -0.0633127000
_diffrn_orient_matrix_UB_31      0.0733216000
_diffrn_orient_matrix_UB_32      0.0223629000
_diffrn_orient_matrix_UB_33      0.0328806000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0307
_diffrn_reflns_av_unetI/netI     0.1147
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.837
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            7638
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.837
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         34.533
_diffrn_reflns_theta_min         2.748
_diffrn_source                   'fine-focus sealed X-ray tube'
_diffrn_source_type              'Rigaku (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    0.231
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.94568
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.39.35c (Rigaku Oxford Diffraction, 2017)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            'clear light colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.528
_exptl_crystal_description       needle
_exptl_crystal_F_000             424
_exptl_crystal_recrystallization_method
'Re-crystallisation from solvent: Methanol'
_exptl_crystal_size_max          0.16
_exptl_crystal_size_mid          0.05
_exptl_crystal_size_min          0.02
_refine_diff_density_max         0.288
_refine_diff_density_min         -0.354
_refine_diff_density_rms         0.065
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.049
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     255
_refine_ls_number_reflns         6296
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.049
_refine_ls_R_factor_all          0.1639
_refine_ls_R_factor_gt           0.0649
_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^)+(0.0606P)^2^] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1512
_refine_ls_wR_factor_ref         0.1882
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2813
_reflns_number_total             6296
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d0ce00924e2.cif
_cod_data_source_block           mbzs3
_cod_database_code               7241105
_shelx_shelxl_version_number     2017/1
_chemical_oxdiff_formula         'C16 H13 N3 O7 S'
_chemical_oxdiff_usercomment     'Sulfato de MBZ'
_reflns_odcompleteness_completeness 99.89
_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
 At 1.5 times of:
  All C(H,H,H) groups
2.a Aromatic/amide H refined with riding coordinates:
 N11(H11), N18(H18), N13(H13), C15(H15), C9(H9), C8(H8), C24(H24), C25(H25),
 C26(H26), C28(H28), C27(H27)
2.b Idealised Me refined as rotating group:
 C21(H21A,H21B,H21C), C4(H4A,H4B,H4C)
;
_shelx_res_checksum              32750
_olex2_submission_original_sample_id 'Metilsulfato de mebendazole'
_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 1.068
_oxdiff_exptl_absorpt_empirical_full_min 0.930