Diastereomeric salts of (S,S)-sertraline with l- and d-tartaric acids: an investigation into chiral supramolecular discrimination
Carvalho, Paulo S.; Diniz, Luan F.; Ayala, Alejandro P.; CrystEngComm 25 (2023) 1693–1702; doi:10.1039/D3CE00094J

data_7246240
_publ_section_title
;
 Diastereomeric salts of (S,S)-sertraline with l- and d-tartaric acids: an
 investigation into chiral supramolecular discrimination
;
_journal_issue                   11
_journal_name_full               CrystEngComm
_journal_page_first              1693
_journal_page_last               1702
_journal_paper_doi               10.1039/D3CE00094J
_journal_volume                  25
_journal_year                    2023
_chemical_absolute_configuration ad
_chemical_formula_moiety         'C17 H18 Cl2 N, C4 H5 O6'
_chemical_formula_sum            'C21 H23 Cl2 N O6'
_chemical_formula_weight         456.30
_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             2023-01-25
_audit_creation_method
;
Olex2 1.5
(compiled 2022.04.07 svn.rca3783a0 for OlexSys, GUI svn.r6498)
;
_audit_update_record
;
2023-01-27 deposited with the CCDC.	2023-02-15 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 96.194(2)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   17.628(2)
_cell_length_b                   5.4719(7)
_cell_length_c                   21.601(3)
_cell_measurement_reflns_used    9881
_cell_measurement_temperature    100.0(2)
_cell_measurement_theta_max      30.94
_cell_measurement_theta_min      2.60
_cell_volume                     2071.4(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  (Sheldrick, 2015)'
_diffrn_ambient_temperature      100.0(2)
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.998
_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  0.0391
_diffrn_reflns_av_unetI/netI     0.0199
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_limit_h_max       22
_diffrn_reflns_limit_h_min       -22
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_l_max       27
_diffrn_reflns_limit_l_min       -27
_diffrn_reflns_number            41429
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.101
_diffrn_reflns_theta_min         2.846
_diffrn_source_current           0.0
_diffrn_source_power             0.0
_diffrn_source_voltage           0.0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.353
_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    1.463
_exptl_crystal_description       plate
_exptl_crystal_F_000             952
_exptl_crystal_size_max          0.16
_exptl_crystal_size_mid          0.064
_exptl_crystal_size_min          0.031
_refine_diff_density_max         0.677
_refine_diff_density_min         -0.822
_refine_diff_density_rms         0.050
_refine_ls_abs_structure_details
;
 Flack x determined using 1808 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.030(18)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.068
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     347
_refine_ls_number_reflns         4549
_refine_ls_number_restraints     62
_refine_ls_restrained_S_all      1.063
_refine_ls_R_factor_all          0.0449
_refine_ls_R_factor_gt           0.0407
_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^)+(0.0253P)^2^+3.8121P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0885
_refine_ls_wR_factor_ref         0.0912
_reflns_Friedel_coverage         0.807
_reflns_Friedel_fraction_full    1.000
_reflns_Friedel_fraction_max     1.000
_reflns_number_gt                4250
_reflns_number_total             4549
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d3ce00094j2.cif
_cod_data_source_block           srt-(l)-tart
_cod_depositor_comments
'Adding full bibliography for 7246240--7246241.cif.'
_cod_database_code               7246240
_shelx_shelxl_version_number     2014/7
_shelx_estimated_absorpt_t_max   0.989
_shelx_estimated_absorpt_t_min   0.946
_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, All O(H) groups
2. Restrained distances
 C12B-C5 \\sim C12-C5
 with sigma of 0.02
3. Uiso/Uaniso restraints and constraints
Uanis(C15B) \\sim Ueq, Uanis(C15) \\sim Ueq: with sigma of 0.1 and sigma for
terminal atoms of 0.2
Uanis(C17B) \\sim Ueq, Uanis(C13) \\sim Ueq: with sigma of 0.1 and sigma for
terminal atoms of 0.2
4. Rigid body (RIGU) restrains
 C12B, C17B, C16B, C15B, C14B, C13B
 with sigma for 1-2 distances of 0.004 and sigma for 1-3 distances of 0.004
5. Others
 Fixed Sof: C12(0.75) C17(0.75) H17(0.75) C16(0.75) C13(0.75) H13(0.75)
 C15(0.75) C14(0.75) H14(0.75) Cl1(0.75) Cl2(0.75) Cl2A(0.25) Cl1A(0.25)
 C12B(0.25) C17B(0.25) H17B(0.25) C13B(0.25) H13B(0.25) C16B(0.25) C14B(0.25)
 H14B(0.25) C15B(0.25) H5A(0.75) H5B(0.25)
6.a Ternary CH refined with riding coordinates:
 C19(H19), C20(H20), C2(H2), C5(H5A), C5(H5B)
6.b Secondary CH2 refined with riding coordinates:
 C3(H3A,H3B), N1(H1A,H1B), C4(H4A,H4B)
6.c Aromatic/amide H refined with riding coordinates:
 C10(H10), C7(H7), C9(H9), C8(H8), C17(H17), C13(H13), C14(H14), C17B(H17B),
 C13B(H13B), C14B(H14B)
6.d Idealised Me refined as rotating group:
 C1(H1C,H1D,H1E)
6.e Idealised tetrahedral OH refined as rotating group:
 O3(H3), O4(H4), O6(H6)
;
_shelx_res_checksum              94045
_shelx_hkl_checksum              85401
_olex2_submission_special_instructions 'No special instructions were received'