Pharmaceutical salt and salt hydrates of vortioxetine with sulfonic acid to ameliorate the solubility and hygroscopicity via the charge-assisted hydrogen bond assembly
Du, Rongkai; Xu, Juan; Li, Jing; Zhang, Lei; Ning, Lifeng; Li, Shan; New Journal of Chemistry 45 (2021) 1474–1481; doi:10.1039/D0NJ05052K

data_7060269
_publ_section_title
;
 Pharmaceutical salt and salt hydrates of vortioxetine with sulfonic acid
 to ameliorate the solubility and hygroscopicity via the charge-assisted
 hydrogen bond assembly
;
_journal_issue                   3
_journal_name_full               'New Journal of Chemistry'
_journal_page_first              1474
_journal_page_last               1481
_journal_paper_doi               10.1039/D0NJ05052K
_journal_volume                  45
_journal_year                    2021
_chemical_formula_moiety         'C18 H23 N2 S, C7 H5 O6 S, H2 O'
_chemical_formula_sum            'C25 H30 N2 O7 S2'
_chemical_formula_weight         534.63
_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   mixed
_atom_sites_solution_primary     dual
_audit_creation_date             2019-08-20
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_audit_update_record
;
2019-10-06 deposited with the CCDC.	2020-12-07 downloaded from the CCDC.
;
_cell_angle_alpha                94.929(5)
_cell_angle_beta                 98.640(5)
_cell_angle_gamma                104.714(5)
_cell_formula_units_Z            2
_cell_length_a                   7.7358(5)
_cell_length_b                   12.5412(8)
_cell_length_c                   13.7109(8)
_cell_measurement_reflns_used    3886
_cell_measurement_temperature    173.00(10)
_cell_measurement_theta_max      28.6700
_cell_measurement_theta_min      3.5550
_cell_volume                     1261.20(14)
_computing_cell_refinement       'CrysAlisPro 1.171.38.41 (Rigaku OD, 2015)'
_computing_data_collection       'CrysAlisPro 1.171.38.41 (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.38.41 (Rigaku OD, 2015)'
_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_environment      N~2~
_diffrn_ambient_temperature      173.00(10)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 16.1213
_diffrn_detector_type            Eos
_diffrn_measured_fraction_theta_full 0.996
_diffrn_measured_fraction_theta_max 0.823
_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    -45.00  85.00   1.00    2.00    --   15.65   0.00   0.00  130
  2  \w     -6.00  22.00   1.00    2.00    --  -16.28 -99.00 150.00   28
  3  \w    -22.00  21.00   1.00    2.00    --  -16.28 -99.00  60.00   43
  4  \w    -51.00  29.00   1.00    2.00    --   15.65 -57.00 150.00   80
  5  \w    -58.00 -17.00   1.00    2.00    --  -16.28 110.00-119.00   41
  6  \w    -67.00   2.00   1.00    2.00    --  -16.28 -77.00   0.00   69
;
_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      -0.0127928000
_diffrn_orient_matrix_UB_12      0.0105636000
_diffrn_orient_matrix_UB_13      -0.0502083000
_diffrn_orient_matrix_UB_21      0.0533005000
_diffrn_orient_matrix_UB_22      -0.0361008000
_diffrn_orient_matrix_UB_23      -0.0117328000
_diffrn_orient_matrix_UB_31      -0.0792361000
_diffrn_orient_matrix_UB_32      -0.0454214000
_diffrn_orient_matrix_UB_33      -0.0112433000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0219
_diffrn_reflns_av_unetI/netI     0.0405
_diffrn_reflns_Laue_measured_fraction_full 0.996
_diffrn_reflns_Laue_measured_fraction_max 0.823
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            10892
_diffrn_reflns_point_group_measured_fraction_full 0.996
_diffrn_reflns_point_group_measured_fraction_max 0.823
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         29.415
_diffrn_reflns_theta_min         3.527
_diffrn_source                   'fine-focus sealed X-ray tube'
_diffrn_source_type              'Enhance (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    0.260
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.11730
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.38.41 (Rigaku Oxford Diffraction, 2015)
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    1.408
_exptl_crystal_description       block
_exptl_crystal_F_000             564
_exptl_crystal_size_max          0.37
_exptl_crystal_size_mid          0.34
_exptl_crystal_size_min          0.15
_refine_diff_density_max         0.358
_refine_diff_density_min         -0.447
_refine_diff_density_rms         0.051
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.031
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     351
_refine_ls_number_reflns         5739
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.031
_refine_ls_R_factor_all          0.0542
_refine_ls_R_factor_gt           0.0394
_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^)+(0.0468P)^2^+0.3355P]
 where P=(Fo^2^+2Fc^2^)/3
;
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0953
_refine_ls_wR_factor_ref         0.1035
_reflns_Friedel_coverage         0.000
_reflns_number_gt                4584
_reflns_number_total             5739
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d0nj05052k2.cif
_cod_data_source_block           VOT-SSA-H2O
_cod_depositor_comments
'Adding full bibliography for 7060266--7060269.cif.'
_cod_database_code               7060269
_shelxl_version_number           2013-2
_shelx_estimated_absorpt_t_max   0.962
_shelx_estimated_absorpt_t_min   0.910
_reflns_odcompleteness_completeness 99.67
_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 C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Secondary CH2 refined with riding coordinates:
 C1(H1A,H1B), C2(H2A,H2B), C3(H3A,H3B), C4(H4A,H4B)
2.b Aromatic/amide H refined with riding coordinates:
 C6(H6), C7(H7), C8(H8), C9(H9), C13(H13), C15(H15), C16(H16), C21(H21),
 C22(H22), C24(H24)
2.c Idealised Me refined as rotating group:
 C17(H17A,H17B,H17C), C18(H18A,H18B,H18C)
;
_shelx_res_checksum              81808
_shelx_hkl_checksum              45803
_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 8.326
_oxdiff_exptl_absorpt_empirical_full_min 0.528