Pharmaceutical paroxetine-based organic salts of carboxylic acids with optimized properties: the identification and characterization of potential novel API solid forms
Carvalho, Paulo S.; Diniz, Luan F.; Tenorio, Juan C.; Souza, Matheus S.; Franco, Chris H. J.; Rial, Rafael C.; Warszawski de Oliveira, Karla Regina; Nazario, Carlos E. D.; Ellena, Javier; CrystEngComm 21 (2019) 3668–; doi:10.1039/C8CE02076K

data_7232539
_publ_section_title
;
 Pharmaceutical paroxetine-based organic salts of carboxylic acids with
 optimized properties: the identification and characterization of
 potential novel API solid forms
;
_journal_issue                   24
_journal_name_full               CrystEngComm
_journal_page_first              3668
_journal_paper_doi               10.1039/C8CE02076K
_journal_volume                  21
_journal_year                    2019
_chemical_absolute_configuration ad
_chemical_formula_moiety
'0.5(C4 H4 O6), 0.5(C4 H6 O6), C19 H21 F N O3, 0.5(H2 O)'
_chemical_formula_sum            'C23 H27 F N O9.5'
_chemical_formula_weight         488.45
_chemical_name_common            PRX-TART
_chemical_name_systematic        'Paroxetine tartrate'
_space_group_crystal_system      monoclinic
_space_group_IT_number           4
_space_group_name_Hall           'P 2yb'
_space_group_name_H-M_alt        'P 1 21 1'
_symmetry_space_group_name_Hall  'P 2yb'
_symmetry_space_group_name_H-M   'P 1 21 1'
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     dual
_audit_creation_date             2019-03-10
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_audit_update_record
;
2019-03-11 deposited with the CCDC.    2019-03-25 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 97.036(2)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   14.3395(17)
_cell_length_b                   7.9557(9)
_cell_length_c                   19.608(2)
_cell_measurement_reflns_used    9943
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      27.64
_cell_measurement_theta_min      2.77
_cell_volume                     2220.1(4)
_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      100(2)
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0497
_diffrn_reflns_av_unetI/netI     0.0397
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.996
_diffrn_reflns_limit_h_max       19
_diffrn_reflns_limit_h_min       -19
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       26
_diffrn_reflns_limit_l_min       -26
_diffrn_reflns_number            55494
_diffrn_reflns_point_group_measured_fraction_full 0.996
_diffrn_reflns_point_group_measured_fraction_max 0.992
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         28.395
_diffrn_reflns_theta_min         1.873
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.119
_exptl_absorpt_correction_T_max  0.996
_exptl_absorpt_correction_T_min  0.988
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
'R.H. Blessing, Acta Crystallogr., Sect A 1995, 51, 33-38.'
_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    1.461
_exptl_crystal_description       prism
_exptl_crystal_F_000             1028
_exptl_crystal_size_max          0.101
_exptl_crystal_size_mid          0.064
_exptl_crystal_size_min          0.033
_refine_diff_density_max         0.979
_refine_diff_density_min         -0.332
_refine_diff_density_rms         0.054
_refine_ls_abs_structure_details
;
 Flack x determined using 3868 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.4(2)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.037
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     631
_refine_ls_number_reflns         11054
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.037
_refine_ls_R_factor_all          0.0520
_refine_ls_R_factor_gt           0.0414
_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^)+(0.0494P)^2^+0.8735P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0961
_refine_ls_wR_factor_ref         0.1024
_reflns_Friedel_coverage         0.862
_reflns_Friedel_fraction_full    0.993
_reflns_Friedel_fraction_max     0.988
_reflns_number_gt                9635
_reflns_number_total             11054
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c8ce02076k2.cif
_cod_data_source_block           prx-tart
_cod_depositor_comments
'Adding full bibliography for 7232537--7232540.cif.'
_cod_original_cell_volume        2220.0(4)
_cod_original_formula_sum        'C23 H27 F N O9.50'
_cod_database_code               7232539
_shelx_shelxl_version_number     2014/7
_shelx_estimated_absorpt_t_max   0.996
_shelx_estimated_absorpt_t_min   0.988
_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 O(H) groups, All O(H,H) groups
2.a Free rotating group:
 OW1(HW1A,HW1B)
2.b Ternary CH refined with riding coordinates:
 C2(H2), C3(H3), C6(H6), C7(H7A), C4A(H4A), C5A(H5A), C4B(H4B), C5B(H5B)
2.c Secondary CH2 refined with riding coordinates:
 N1A(H1AA,H1AB), C1A(H1AC,H1AD), C2A(H2AA,H2AB), C3A(H3AA,H3AB), C13A(H13A,
 H13B), N1B(H1BA,H1BB), C1B(H1BC,H1BD), C2B(H2BA,H2BB), C3B(H3BA,H3BB),
 C6A(H6AA,H6AB), C6B(H6BA,H6BB), C13B(H13C,H13D)
2.d Aromatic/amide H refined with riding coordinates:
 C8A(H8A), C9A(H9A), C12A(H12A), C15A(H15A), C16A(H16A), C18A(H18A),
 C19A(H19A), C8B(H8B), C9B(H9B), C12B(H12B), C15B(H15B), C16B(H16B), C18B(H18B),
  C19B(H19B)
2.e Idealised tetrahedral OH refined as rotating group:
 O5(H5), O6(H6A), O7(H7), O9(H9), O10(H10), O11(H11)
;
_shelx_res_checksum              61216
_olex2_submission_special_instructions 'No special instructions were received'