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_7249175
_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         '2(O2 S0.5), 2(C17 H19 F3 N O)'
_chemical_formula_sum            'C34 H38 F6 N2 O6 S'
_chemical_formula_weight         716.72
_chemical_name_systematic        'Fluoxetine sulfate'
_space_group_crystal_system      monoclinic
_space_group_IT_number           5
_space_group_name_Hall           'C 2y'
_space_group_name_H-M_alt        'C 1 2 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_audit_creation_date             2021-10-27
_audit_creation_method
;
Olex2 1.5
(compiled 2021.10.07 svn.r9718050b for OlexSys, GUI svn.r6410)
;
_audit_update_record
;
2024-04-25 deposited with the CCDC.	2024-08-05 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 105.192(3)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   37.617(3)
_cell_length_b                   10.0630(7)
_cell_length_c                   10.2534(7)
_cell_measurement_reflns_used    25.297
_cell_measurement_temperature    298.0(2)
_cell_measurement_theta_max      25.297
_cell_measurement_theta_min      2.070
_cell_volume                     3745.7(5)
_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      296.15
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.974
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0386
_diffrn_reflns_av_unetI/netI     0.0601
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.974
_diffrn_reflns_limit_h_max       45
_diffrn_reflns_limit_h_min       -38
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_number            13009
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.970
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         25.297
_diffrn_reflns_theta_min         2.070
_exptl_absorpt_coefficient_mu    0.159
_exptl_absorpt_correction_T_max  0.7452
_exptl_absorpt_correction_T_min  0.6183
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
SADABS-2008/1 (Bruker,2008) was used for absorption correction.
wR2(int) was 0.1312 before and 0.0603 after correction.
The Ratio of minimum to maximum transmission is 0.8297.
The \l/2 correction factor is 0.0015.
;
_exptl_crystal_density_diffrn    1.271
_exptl_crystal_description       prism
_exptl_crystal_F_000             1496
_exptl_crystal_size_max          0.281
_exptl_crystal_size_mid          0.248
_exptl_crystal_size_min          0.126
_refine_diff_density_max         0.651
_refine_diff_density_min         -0.259
_refine_diff_density_rms         0.069
_refine_ls_abs_structure_details
;
 Flack x determined using 1487 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.09(6)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.035
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     464
_refine_ls_number_reflns         6542
_refine_ls_number_restraints     73
_refine_ls_restrained_S_all      1.035
_refine_ls_R_factor_all          0.1179
_refine_ls_R_factor_gt           0.0828
_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^)+(0.1786P)^2^] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2323
_refine_ls_wR_factor_ref         0.2670
_reflns_Friedel_coverage         0.879
_reflns_Friedel_fraction_full    0.998
_reflns_Friedel_fraction_max     0.967
_reflns_number_gt                4251
_reflns_number_total             6542
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d4ce00643g2.cif
_cod_data_source_block           flu_so4_mo_298k
_cod_depositor_comments
'Adding full bibliography for 7249175--7249177.cif.'
_cod_database_code               7249175
_shelx_shelxl_version_number     2014/7
_olex2_refinement_description
;
1. Twinned data refinement
 Scales: 0.97307
 0.02693
2. Rigid body (RIGU) restrains
 O5B, O4B
 with sigma for 1-2 distances of 0.004 and sigma for 1-3 distances of 0.004
 O5, O4
 with sigma for 1-2 distances of 0.004 and sigma for 1-3 distances of 0.004
 C3, C2, C1, C6, C5, C4
 with sigma for 1-2 distances of 0.004 and sigma for 1-3 distances of 0.004
 C6', C1', C2', C3', C4', C5'
 with sigma for 1-2 distances of 0.004 and sigma for 1-3 distances of 0.004
3. Others
 Fixed Sof: O4(0.55) O5(0.55) O5B(0.45) O4B(0.45)
4.a Ternary CH refined with riding coordinates:
 C7S(H7S), C7R(H7R)
4.b Secondary CH2 refined with riding coordinates:
 N004(H00A,H00B), N007(H00C,H00D), C9'(H9'A,H9'B), C8(H8A,H8B), C9(H9A,H9B),
 C8'(H8'A,H8'B)
4.c Aromatic/amide H refined with riding coordinates:
 C12(H12), C5(H5), C13'(H13'), C16'(H16'), C12'(H12'), C5'(H5'), C15(H15),
 C4'(H4'), C1(H1), C3'(H3'), C13(H13), C2(H2), C2'(H2'), C16(H16), C15'(H15'),
 C3(H3), C1'(H1'), C4(H4)
4.d Idealised Me refined as rotating group:
 C10'(H10A,H10B,H10C), C10(H10D,H10E,H10F)
;
_olex2_submission_special_instructions 'No special instructions were received'