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_7232540
_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         'C19 H21 F N O3, C4 H3 O4'
_chemical_formula_sum            'C23 H24 F N O7'
_chemical_formula_weight         445.43
_chemical_name_common            PRX-MAL
_chemical_name_systematic        'Paroxetine maleate'
_space_group_crystal_system      triclinic
_space_group_IT_number           1
_space_group_name_Hall           'P 1'
_space_group_name_H-M_alt        'P 1'
_symmetry_space_group_name_Hall  'P 1'
_symmetry_space_group_name_H-M   'P 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                77.740(4)
_cell_angle_beta                 77.333(4)
_cell_angle_gamma                71.079(3)
_cell_formula_units_Z            4
_cell_length_a                   11.629(2)
_cell_length_b                   11.649(2)
_cell_length_c                   17.584(5)
_cell_measurement_reflns_used    44075
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      26.372
_cell_measurement_theta_min      2.230
_cell_volume                     2172.6(8)
_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 0.999
_diffrn_measured_fraction_theta_max 0.988
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0430
_diffrn_reflns_av_unetI/netI     0.0515
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.988
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_number            44075
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.987
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         26.372
_diffrn_reflns_theta_min         2.230
_exptl_absorpt_coefficient_mu    0.106
_exptl_absorpt_correction_T_max  0.994
_exptl_absorpt_correction_T_min  0.979
_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    1.362
_exptl_crystal_description       prism
_exptl_crystal_F_000             936
_exptl_crystal_size_max          0.196
_exptl_crystal_size_mid          0.157
_exptl_crystal_size_min          0.06
_refine_diff_density_max         0.692
_refine_diff_density_min         -0.344
_refine_diff_density_rms         0.092
_refine_ls_abs_structure_details
;
 Flack x determined using 7124 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.1(4)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.040
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     1148
_refine_ls_number_reflns         16775
_refine_ls_number_restraints     174
_refine_ls_restrained_S_all      1.038
_refine_ls_R_factor_all          0.0666
_refine_ls_R_factor_gt           0.0654
_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^)+(0.1176P)^2^+1.4441P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1687
_refine_ls_wR_factor_ref         0.1708
_reflns_Friedel_coverage         0.999
_reflns_Friedel_fraction_full    0.998
_reflns_Friedel_fraction_max     0.987
_reflns_number_gt                16370
_reflns_number_total             16775
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c8ce02076k2.cif
_cod_data_source_block           prx_mal
_cod_depositor_comments
'Adding full bibliography for 7232537--7232540.cif.'
_cod_original_cell_volume        2172.6(9)
_cod_database_code               7232540
_shelx_shelxl_version_number     2014/7
_shelx_estimated_absorpt_t_max   0.994
_shelx_estimated_absorpt_t_min   0.979
_olex2_refinement_description
;
1. Twinned data refinement
 Scales: 0.7444(18)
 0.2556(18)
2. 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
3. Uiso/Uaniso restraints and constraints
Uanis(C11A) = Uanis(C10A)
4. Rigid body (RIGU) restrains
 C14B, C19B, C18B, C17B, C16B, C15B
 with sigma for 1-2 distances of 0.004 and sigma for 1-3 distances of 0.004
 C17A, C16A, C15A, C14A, C19A, C18A
 with sigma for 1-2 distances of 0.004 and sigma for 1-3 distances of 0.004
 O3A, C11A, C10A, O2A, C13A
 with sigma for 1-2 distances of 0.004 and sigma for 1-3 distances of 0.004
 C7A, C8A, C9A, C10A, C11A, C12A
 with sigma for 1-2 distances of 0.004 and sigma for 1-3 distances of 0.004
 C11C, C10C, C9C, C8C, C7C, C12C
 with sigma for 1-2 distances of 0.004 and sigma for 1-3 distances of 0.004
5.a Riding coordinates:
 O6A(H6A), O6B(H6B), O6C(H6C), O6D(H6D)
5.b Ternary CH refined with riding coordinates:
 C4A(H4A), C5A(H5A), C4B(H4B), C5B(H5B), C4C(H4C), C5C(H5C), C4D(H4D), C5D(H5D)
5.c Secondary CH2 refined with riding coordinates:
 N1A(H1AA,H1AB), C1A(H1AC,H1AD), C2A(H2AA,H2AB), C3A(H3AA,H3AB), C6A(H6AA,
 H6AB), C13A(H13A,H13B), N1B(H1BA,H1BB), C1B(H1BC,H1BD), C2B(H2BA,H2BB),
 C3B(H3BA,H3BB), C6B(H6BA,H6BB), C13B(H13C,H13D), N1C(H1CA,H1CB), C1C(H1CC,
 H1CD), C2C(H2CA,H2CB), C3C(H3CA,H3CB), C6C(H6CA,H6CB), C13C(H13E,H13F),
 N1D(H1DA,H1DB), C1D(H1DC,H1DD), C2D(H2DA,H2DB), C3D(H3DA,H3DB), C6D(H6DA,H6DB),
  C13D(H13G,H13H)
5.d Aromatic/amide H refined with riding coordinates:
 C8A(H8A), C9A(H9A), C12A(H12A), C15A(H15A), C16A(H16A), C18A(H18A),
 C19A(H19A), C21A(H21A), C22A(H22A), C8B(H8B), C9B(H9B), C12B(H12B), C15B(H15B),
  C16B(H16B), C18B(H18B), C19B(H19B), C21B(H21B), C22B(H22B), C8C(H8C),
 C9C(H9C), C12C(H12C), C15C(H15C), C16C(H16C), C18C(H18C), C19C(H19C),
 C21C(H21C), C22C(H22C), C8D(H8D), C9D(H9D), C12D(H12D), C15D(H15D), C16D(H16D),
  C18D(H18D), C19D(H19D), C21D(H21D), C22D(H22D)
;
_shelx_res_checksum              74630
_olex2_submission_special_instructions 'No special instructions were received'