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_7232537
_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 rm
_chemical_formula_moiety         'C2 O4, 2(C19 H21 F N O3), 0.5(O2H4)'
_chemical_formula_sum            'C40 H44 F2 N2 O11'
_chemical_formula_weight         766.78
_chemical_name_common            PRX-OXA
_chemical_name_systematic        'Paroxetine oxalate'
_space_group_crystal_system      monoclinic
_space_group_IT_number           5
_space_group_name_Hall           'I 2y'
_space_group_name_H-M_alt        'I 1 2 1'
_symmetry_space_group_name_Hall  'I 2y'
_symmetry_space_group_name_H-M   'I 1 2 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                90
_cell_angle_beta                 91.638(14)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   18.960(3)
_cell_length_b                   6.7993(11)
_cell_length_c                   29.935(5)
_cell_measurement_reflns_used    2690
_cell_measurement_temperature    298(2)
_cell_measurement_theta_max      22.6530
_cell_measurement_theta_min      3.0560
_cell_volume                     3857.5(11)
_computing_cell_refinement       'CrysAlisPro 1.171.39.35c (Rigaku OD, 2017)'
_computing_data_collection       'CrysAlisPro 1.171.39.35c (Rigaku OD, 2017)'
_computing_data_reduction        'CrysAlisPro 1.171.39.35c (Rigaku OD, 2017)'
_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      298(2)
_diffrn_detector                 'CCD plate'
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_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    -65.00 -38.00   1.00  162.50    --   27.63  54.00   0.00   27
  2  \w     19.00 118.00   1.00  162.50    --   27.63  54.00   0.00   99
  3  \w    -69.00 -43.00   1.00  162.50    --   27.63  54.00-120.00   26
  4  \w     16.00  41.00   1.00  162.50    --   27.63  54.00-120.00   25
  5  \w     30.00  57.00   1.00  162.50    --   27.63  54.00 -90.00   27
  6  \w    -69.00 116.00   1.00  162.50    --   27.63  54.00 120.00  185
;
_diffrn_measurement_device       'two-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB Mini (ROW)'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0302899000
_diffrn_orient_matrix_UB_12      -0.0124791000
_diffrn_orient_matrix_UB_13      0.0141830000
_diffrn_orient_matrix_UB_21      0.0219384000
_diffrn_orient_matrix_UB_22      0.0082573000
_diffrn_orient_matrix_UB_23      -0.0186838000
_diffrn_orient_matrix_UB_31      0.0015841000
_diffrn_orient_matrix_UB_32      0.1032268000
_diffrn_orient_matrix_UB_33      0.0034104000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0663
_diffrn_reflns_av_unetI/netI     0.0903
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_limit_h_max       23
_diffrn_reflns_limit_h_min       -23
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_l_max       37
_diffrn_reflns_limit_l_min       -37
_diffrn_reflns_number            13051
_diffrn_reflns_point_group_measured_fraction_full 0.960
_diffrn_reflns_point_group_measured_fraction_max 0.956
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         26.372
_diffrn_reflns_theta_min         2.723
_diffrn_source                   'fine-focus sealed X-ray tube'
_diffrn_source_type              'Rigaku (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    0.102
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.77596
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.39.35c (Rigaku Oxford Diffraction, 2017)
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    1.317
_exptl_crystal_description       prism
_exptl_crystal_F_000             1608
_exptl_crystal_size_max          0.35
_exptl_crystal_size_mid          0.11
_exptl_crystal_size_min          0.06
_refine_diff_density_max         0.286
_refine_diff_density_min         -0.240
_refine_diff_density_rms         0.052
_refine_ls_abs_structure_details
;
 Flack x determined using 917 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   1.1(10)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.021
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     505
_refine_ls_number_reflns         7554
_refine_ls_number_restraints     73
_refine_ls_restrained_S_all      1.027
_refine_ls_R_factor_all          0.1338
_refine_ls_R_factor_gt           0.0774
_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^)+(0.1131P)^2^] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2097
_refine_ls_wR_factor_ref         0.2645
_reflns_Friedel_coverage         0.761
_reflns_Friedel_fraction_full    0.915
_reflns_Friedel_fraction_max     0.906
_reflns_number_gt                3878
_reflns_number_total             7554
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c8ce02076k2.cif
_cod_data_source_block           prx-oxa
_cod_depositor_comments
'Adding full bibliography for 7232537--7232540.cif.'
_cod_original_cell_volume        3857.5(10)
_cod_database_code               7232537
_shelx_shelxl_version_number     2014/7
_chemical_oxdiff_formula         'C21 H20 N1 O7 F1'
_shelx_estimated_absorpt_t_max   0.994
_shelx_estimated_absorpt_t_min   0.965
_reflns_odcompleteness_completeness 99.81
_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
2. Rigid body (RIGU) restrains
 C16B, C15B, C14B, C19B, C18B, C17B
 with sigma for 1-2 distances of 0.004 and sigma for 1-3 distances of 0.004
 C15A, C16A, C17A, C18A, C19A, C14A
 with sigma for 1-2 distances of 0.004 and sigma for 1-3 distances of 0.004
3. Others
 Fixed Sof: OW1(0.5) OW2(0.5)
4.a Ternary CH refined with riding coordinates:
 C4A(H4A), C5A(H5A), C4B(H4B), C5B(H5B)
4.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)
4.c Aromatic/amide H refined with riding coordinates:
 C8A(H8A), C9A(H9A), C12A(H12A), C15A(H15A), C16A(H16A), C18B(H18B),
 C18A(H18A), C19A(H19A), C8B(H8B), C9B(H9B), C12B(H12B), C15B(H15B), C16B(H16B),
  C19B(H19B)
;
_shelx_res_checksum              64461
_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 1.235
_oxdiff_exptl_absorpt_empirical_full_min 0.826