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_7249176
_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_formula_moiety         '0.494(O4 S), C17 H19 F3 N O, H2 O'
_chemical_formula_sum            'C17 H21 F3 N O3.97 S0.5'
_chemical_formula_weight         375.98
_chemical_name_systematic        'Fluoxetine sulfate hydrate'
_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   mixed
_atom_sites_solution_primary     dual
_audit_creation_date             2024-01-30
_audit_creation_method
;
Olex2 1.5
(compiled 2023.08.24 svn.re1ec1418 for OlexSys, GUI svn.r6817)
;
_audit_update_record
;
2024-04-25 deposited with the CCDC.	2024-08-05 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 106.070(11)
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   36.047(7)
_cell_length_b                   10.1156(17)
_cell_length_c                   10.3307(16)
_cell_measurement_reflns_used    9172
_cell_measurement_temperature    100.00
_cell_measurement_theta_max      26.39
_cell_measurement_theta_min      2.66
_cell_volume                     3619.8(11)
_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      100.00
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.978
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0873
_diffrn_reflns_av_unetI/netI     0.0418
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.978
_diffrn_reflns_limit_h_max       42
_diffrn_reflns_limit_h_min       -42
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_number            62222
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.977
_diffrn_reflns_theta_full        25.023
_diffrn_reflns_theta_max         25.023
_diffrn_reflns_theta_min         2.051
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.172
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            colourless
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.380
_exptl_crystal_description       prism
_exptl_crystal_F_000             1574
_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.17
_refine_diff_density_max         0.890
_refine_diff_density_min         -0.981
_refine_diff_density_rms         0.147
_refine_ls_abs_structure_details
;
 Flack x determined using 2347 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.11(3)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.086
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     329
_refine_ls_number_reflns         6370
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.086
_refine_ls_R_factor_all          0.1398
_refine_ls_R_factor_gt           0.1315
_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^)+100.6538P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2832
_refine_ls_wR_factor_ref         0.2879
_reflns_Friedel_coverage         0.883
_reflns_Friedel_fraction_full    1.000
_reflns_Friedel_fraction_max     0.976
_reflns_number_gt                5860
_reflns_number_total             6370
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d4ce00643g2.cif
_cod_data_source_block           flx-so4-h
_cod_depositor_comments
'Adding full bibliography for 7249175--7249177.cif.'
_cod_original_formula_sum        'C17 H21 F3 N O3.97 S0.50'
_cod_database_code               7249176
_shelx_shelxl_version_number     2014/7
_shelx_estimated_absorpt_t_max   0.971
_shelx_estimated_absorpt_t_min   0.966
_olex2_refinement_description
;
1. Twinned data refinement
 Scales: 0.957(3)
 0.043(3)
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 C(H,H,H) groups, All O(H,H) groups
3. Uiso/Uaniso restraints and constraints
Uanis(O01G) = Uanis(O008)
Uanis(C017) = Uanis(C01B) = Uanis(C01D) = Uanis(C018) = Uanis(C01A) =
Uanis(C014)
Uanis(C00B) = Uanis(C012)
Uanis(O1) = Uanis(O011)
Uanis(O01F) = Uanis(O1) = Uanis(O011)
Uanis(O0) = Uanis(O2)
Uanis(C00V) = Uanis(C012)
Uanis(C00O) = Uanis(C00G) = Uanis(C00N) = Uanis(C00U) = Uanis(C00H) =
Uanis(C00M)
Uanis(C00J) = Uanis(C013) = Uanis(C00W) = Uanis(C00Y) = Uanis(C00R) =
Uanis(C00E)
Uanis(C00F) = Uanis(C010) = Uanis(C00P) = Uanis(C00K) = Uanis(C015) =
Uanis(C00Q)
Uanis(O00C) = Uanis(O0) = Uanis(O2)
4. Others
 Fixed Sof: O0(0.5) H0A(0.5) H0B(0.5) O01F(0.5) O1(0.45) O2(0.5) H2A(0.5)
 H2B(0.5)
5.a Free rotating group:
 O00C(H00M,H00N), O0(H0A,H0B), O2(H2A,H2B)
5.b Ternary CH refined with riding coordinates:
 C00V(H00V), C00X(H00X)
5.c Secondary CH2 refined with riding coordinates:
 N00A(H00F,H00I), C00B(H00A,H00B), N00D(H00C,H00D), C012(H01A,H01B), C016(H01F,
 H01G), C019(H01H,H01I)
5.d Aromatic/amide H refined with riding coordinates:
 C00E(H00E), C00G(H00G), C00H(H00H), C00O(H00O), C00P(H00P), C00Q(H00Q),
 C00R(H00R), C00U(H00U), C00W(H00W), C00Y(H00Y), C010(H010), C013(H013),
 C014(H014), C015(H015), C018(H018), C01A(H01J), C01B(H01K), C01D(H01L)
5.e Idealised Me refined as rotating group:
 C00T(H00J,H00K,H00L), C01E(H01C,H01D,H01E)
;
_shelx_res_checksum              59026
_shelx_hkl_checksum              50368
_olex2_submission_special_instructions 'No special instructions were received'