Spontaneous resolution of RS-fluoxetine through tetrafluoroborate conglomerate salt and racemic kryptoracemate formation via the sulfate ion
Carvalho, Paulo S.; Diniz, Luan F.; Fernandes, Christian; CrystEngComm 26 (2024) 4975–4984; doi:10.1039/D4CE00643G

data_7249177
_publ_section_title
;
 Spontaneous resolution of RS-fluoxetine through tetrafluoroborate
 conglomerate salt and racemic kryptoracemate formation via the sulfate
 ion
;
_journal_issue                   36
_journal_name_full               CrystEngComm
_journal_page_first              4975
_journal_page_last               4984
_journal_paper_doi               10.1039/D4CE00643G
_journal_volume                  26
_journal_year                    2024
_chemical_absolute_configuration ad
_chemical_formula_moiety         'C17 H19 F3 N O, B F4'
_chemical_formula_sum            'C17 H19 B F7 N O'
_chemical_formula_weight         397.14
_chemical_name_systematic        '(S)-Fluoxetine tetrafluoroborate'
_space_group_crystal_system      orthorhombic
_space_group_IT_number           19
_space_group_name_Hall           'P 2ac 2ab'
_space_group_name_H-M_alt        'P 21 21 21'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_audit_creation_date             2024-04-25
_audit_creation_method
;
Olex2 1.5
(compiled 2024.02.16 svn.r378c4104 for OlexSys, GUI svn.r6928)
;
_audit_update_record
;
2024-04-25 deposited with the CCDC.	2024-08-05 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   6.0800(19)
_cell_length_b                   10.8900(16)
_cell_length_c                   27.600(3)
_cell_measurement_reflns_used    5554
_cell_measurement_temperature    100.0(2)
_cell_measurement_theta_max      28.599
_cell_measurement_theta_min      1.391
_cell_volume                     1827.4(7)
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2014/7 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_diffrn_ambient_temperature      100.0(2)
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.990
_diffrn_measurement_device
'Manaca beamline,Sirius (Brazilian Synchrotron Light Laboratory, PILATUS2M'
_diffrn_radiation_type           synchrotron
_diffrn_radiation_wavelength     0.670185
_diffrn_reflns_av_R_equivalents  0.0393
_diffrn_reflns_av_unetI/netI     0.0118
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.990
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       37
_diffrn_reflns_limit_l_min       -37
_diffrn_reflns_number            122396
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.992
_diffrn_reflns_theta_full        23.710
_diffrn_reflns_theta_max         28.599
_diffrn_reflns_theta_min         1.391
_diffrn_source                   synchrotron
_exptl_absorpt_coefficient_mu    0.120
_exptl_absorpt_correction_type   none
_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    1.443
_exptl_crystal_description       prism
_exptl_crystal_F_000             816
_exptl_crystal_size_max          0.4
_exptl_crystal_size_mid          0.107
_exptl_crystal_size_min          0.07
_refine_diff_density_max         0.511
_refine_diff_density_min         -0.347
_refine_diff_density_rms         0.045
_refine_ls_abs_structure_details
;
 Flack x determined using 2348 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.08(5)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.064
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     245
_refine_ls_number_reflns         5554
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.064
_refine_ls_R_factor_all          0.0322
_refine_ls_R_factor_gt           0.0320
_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^)+(0.0541P)^2^+0.3866P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0907
_refine_ls_wR_factor_ref         0.0909
_reflns_Friedel_coverage         0.746
_reflns_Friedel_fraction_full    1.000
_reflns_Friedel_fraction_max     0.995
_reflns_number_gt                5518
_reflns_number_total             5554
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d4ce00643g2.cif
_cod_data_source_block           crd001-1-01_0002_run0_merged_hkl4_sg19
_cod_depositor_comments
'Adding full bibliography for 7249175--7249177.cif.'
_cod_database_code               7249177
_shelx_shelxl_version_number     2014/7
_shelx_estimated_absorpt_t_max   0.992
_shelx_estimated_absorpt_t_min   0.954
_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 Ternary CH refined with riding coordinates:
 C1(H1)
2.b Secondary CH2 refined with riding coordinates:
 N1(H1A,H1B), C2(H2A,H2B), C3(H3A,H3B)
2.c Aromatic/amide H refined with riding coordinates:
 C12(H12), C8(H8), C13(H13), C9(H9), C10(H10), C15(H15), C16(H16), C7(H7),
 C6(H6)
2.d Idealised Me refined as rotating group:
 C4(H4A,H4B,H4C)
;
_shelx_res_checksum              15505
_shelx_hkl_checksum              53000
_olex2_submission_special_instructions 'No special instructions were received'