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_7060267
_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 H7 O3 S'
_chemical_formula_sum            'C25 H30 N2 O3 S2'
_chemical_formula_weight         470.63
_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             2019-12-09
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_audit_update_record
;
2020-02-28 deposited with the CCDC.	2020-12-07 downloaded from the CCDC.
;
_cell_angle_alpha                71.121(7)
_cell_angle_beta                 86.114(5)
_cell_angle_gamma                87.188(6)
_cell_formula_units_Z            4
_cell_length_a                   6.3667(4)
_cell_length_b                   17.6099(15)
_cell_length_c                   23.2688(15)
_cell_measurement_reflns_used    3552
_cell_measurement_temperature    373.0(3)
_cell_measurement_theta_max      23.7030
_cell_measurement_theta_min      4.0040
_cell_volume                     2461.8(3)
_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      air
_diffrn_ambient_temperature      373.0(3)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 16.1213
_diffrn_detector_type            Eos
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.834
_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      4.00  43.20   0.80    5.00    --  -16.28  38.00   0.00   49
  2  \w      2.00  85.20   0.80    5.00    --   15.65  38.00 -60.00  104
  3  \w    -29.00   0.60   0.80    5.00    --  -16.28  57.00 120.00   37
  4  \w    -53.00  35.00   0.80    5.00    --   15.65 -38.00 120.00  110
  5  \w    -14.00  22.80   0.80    5.00    --  -16.28 -99.00 -90.00   46
  6  \w    -25.00   2.20   0.80    5.00    --  -16.28 -99.00-180.00   34
  7  \w    -80.00   0.00   0.80    5.00    --  -16.28 -57.00   0.00  100
  8  \w     35.00  64.60   0.80    5.00    --   15.65 178.00 -60.00   37
;
_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      -0.0739455000
_diffrn_orient_matrix_UB_12      -0.0292137000
_diffrn_orient_matrix_UB_13      0.0162594000
_diffrn_orient_matrix_UB_21      0.0729483000
_diffrn_orient_matrix_UB_22      -0.0168238000
_diffrn_orient_matrix_UB_23      0.0227992000
_diffrn_orient_matrix_UB_31      -0.0411082000
_diffrn_orient_matrix_UB_32      0.0260208000
_diffrn_orient_matrix_UB_33      0.0160259000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0684
_diffrn_reflns_av_unetI/netI     0.1242
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.834
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       23
_diffrn_reflns_limit_k_min       -23
_diffrn_reflns_limit_l_max       29
_diffrn_reflns_limit_l_min       -29
_diffrn_reflns_number            21772
_diffrn_reflns_point_group_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.834
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         29.404
_diffrn_reflns_theta_min         3.467
_diffrn_source                   'fine-focus sealed X-ray tube'
_diffrn_source_type              'Enhance (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    0.245
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.73425
_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    1.270
_exptl_crystal_description       block
_exptl_crystal_F_000             1000
_exptl_crystal_size_max          0.3
_exptl_crystal_size_mid          0.28
_exptl_crystal_size_min          0.24
_refine_diff_density_max         1.335
_refine_diff_density_min         -0.424
_refine_diff_density_rms         0.142
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.393
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     582
_refine_ls_number_reflns         11341
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.393
_refine_ls_R_factor_all          0.2680
_refine_ls_R_factor_gt           0.1815
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
;
 w=1/[\s^2^(Fo^2^)+(0.2000P)^2^]
 where P=(Fo^2^+2Fc^2^)/3
;
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.4551
_refine_ls_wR_factor_ref         0.5054
_reflns_Friedel_coverage         0.000
_reflns_number_gt                4967
_reflns_number_total             11341
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d0nj05052k2.cif
_cod_data_source_block           VOT-TA
_cod_depositor_comments
'Adding full bibliography for 7060266--7060269.cif.'
_cod_database_code               7060267
_shelxl_version_number           2013-2
_shelx_estimated_absorpt_t_max   0.944
_shelx_estimated_absorpt_t_min   0.930
_reflns_odcompleteness_completeness 99.75
_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, All N(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Everything fixed:
 H18A, H18B, H18C
2.b Secondary CH2 refined with riding coordinates:
 C1A(H1AA,H1AB), N1A(H1AC,H1AD), C2A(H2AA,H2AB), C3A(H3AA,H3AB), C4A(H4AA,
 H4AB), C1B(H1BA,H1BB), N1B(H1BC,H1BD), C2B(H2BA,H2BB), C3B(H3BA,H3BB),
 C4B(H4BA,H4BB)
2.c Aromatic/amide H refined with riding coordinates:
 C6A(H6A), C7A(H7A), C8A(H8A), C9A(H9A), C13A(H13A), C15A(H15A), C16A(H16A),
 C6B(H6B), C7B(H7B), C8B(H8B), C9B(H9B), C13B(H13B), C15B(H15B), C16B(H16B),
 C20A(H20A), C21A(H21A), C23A(H23A), C24A(H24A), C20B(H20B), C21B(H21B),
 C23B(H23B), C24B(H24B)
2.d Idealised Me refined as rotating group:
 C17A(H17A,H17B,H17C), C17B(H17D,H17E,H17F), C18B(H18D,H18E,H18F), C25A(H25A,
 H25B,H25C), C25B(H25D,H25E,H25F)
;
_shelx_res_checksum              89328
_shelx_hkl_checksum              9043
_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 1.508
_oxdiff_exptl_absorpt_empirical_full_min 0.694