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_7232538
_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-FUM
_chemical_name_systematic        'Paroxetine fumarate'
_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   geom
_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                78.672(10)
_cell_angle_beta                 82.396(5)
_cell_angle_gamma                85.860(7)
_cell_formula_units_Z            2
_cell_length_a                   7.2223(3)
_cell_length_b                   7.9950(10)
_cell_length_c                   18.538(2)
_cell_measurement_reflns_used    38820
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      25.242
_cell_measurement_theta_min      2.849
_cell_volume                     1039.17(18)
_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 0.993
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measurement_device_type  'Bruker AXS Enraf-Nonius KappaCCD'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0383
_diffrn_reflns_av_unetI/netI     0.0412
_diffrn_reflns_Laue_measured_fraction_full 0.993
_diffrn_reflns_Laue_measured_fraction_max 0.996
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       28
_diffrn_reflns_limit_l_min       -28
_diffrn_reflns_number            38812
_diffrn_reflns_point_group_measured_fraction_full 0.991
_diffrn_reflns_point_group_measured_fraction_max 0.980
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         33.098
_diffrn_reflns_theta_min         2.849
_exptl_absorpt_coefficient_mu    0.111
_exptl_absorpt_correction_T_max  0.98361
_exptl_absorpt_correction_T_min  0.96640
_exptl_absorpt_correction_type   gaussian
_exptl_absorpt_process_details
'P. Coppens in Crystallographic Computing ed F.R. Ahmed, S.R. Hall and C.P. Huber, Copenhagen, Munksgaard, (1970) pp 255-270'
_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    1.424
_exptl_crystal_description       prism
_exptl_crystal_F_000             468
_exptl_crystal_size_max          0.38
_exptl_crystal_size_mid          0.27
_exptl_crystal_size_min          0.2
_refine_diff_density_max         0.398
_refine_diff_density_min         -0.256
_refine_diff_density_rms         0.050
_refine_ls_abs_structure_details
;
 Flack x determined using 6742 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.2(2)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.048
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     579
_refine_ls_number_reflns         15464
_refine_ls_number_restraints     3
_refine_ls_restrained_S_all      1.048
_refine_ls_R_factor_all          0.0432
_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^)+(0.0612P)^2^+0.1507P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1026
_refine_ls_wR_factor_ref         0.1061
_reflns_Friedel_coverage         0.968
_reflns_Friedel_fraction_full    0.988
_reflns_Friedel_fraction_max     0.964
_reflns_number_gt                14521
_reflns_number_total             15464
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c8ce02076k2.cif
_cod_data_source_block           prx-fum
_cod_depositor_comments
'Adding full bibliography for 7232537--7232540.cif.'
_cod_original_cell_volume        1039.16(19)
_cod_database_code               7232538
_shelx_shelxl_version_number     2014/7
_shelx_estimated_absorpt_t_max   0.978
_shelx_estimated_absorpt_t_min   0.959
_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
2.a Ternary CH refined with riding coordinates:
 C4A(H4A), C5A(H5A), C4B(H4B), C5B(H5B)
2.b 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)
2.c 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)
2.d Idealised tetrahedral OH refined as rotating group:
 O6A(H6A), O6B(H6B)
;
_shelx_res_checksum              29611
_olex2_submission_special_instructions 'No special instructions were received'