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_7246241
_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, 2(H2 O)'
_chemical_formula_sum            'C21 H27 Cl2 N O8'
_chemical_formula_weight         492.33
_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   mixed
_atom_sites_solution_primary     dual
_audit_creation_date             2023-01-27
_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                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   7.1781(3)
_cell_length_b                   7.8320(3)
_cell_length_c                   41.7968(16)
_cell_measurement_reflns_used    9903
_cell_measurement_temperature    298.0(2)
_cell_measurement_theta_max      71.44
_cell_measurement_theta_min      4.23
_cell_volume                     2349.77(16)
_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 2018/2 (Sheldrick, 2018)'
_diffrn_ambient_temperature      298.0(2)
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.0999
_diffrn_reflns_av_unetI/netI     0.0689
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       51
_diffrn_reflns_limit_l_min       -50
_diffrn_reflns_number            36659
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_theta_full        67.679
_diffrn_reflns_theta_max         72.113
_diffrn_reflns_theta_min         4.231
_exptl_absorpt_coefficient_mu    2.892
_exptl_absorpt_correction_T_max  0.7536
_exptl_absorpt_correction_T_min  0.5106
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.1655 before and 0.0831 after correction.
The Ratio of minimum to maximum transmission is 0.6775.
The \l/2 correction factor is Not present.
;
_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    1.392
_exptl_crystal_description       plate
_exptl_crystal_F_000             1032
_exptl_crystal_size_max          0.22
_exptl_crystal_size_mid          0.093
_exptl_crystal_size_min          0.038
_refine_diff_density_max         0.316
_refine_diff_density_min         -0.339
_refine_diff_density_rms         0.055
_refine_ls_abs_structure_details
;
 Flack x determined using 1279 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.111(13)
_refine_ls_extinction_coef       0.0036(8)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2014/7 (Sheldrick 2014'
_refine_ls_goodness_of_fit_ref   1.039
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     299
_refine_ls_number_reflns         4616
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.039
_refine_ls_R_factor_all          0.0718
_refine_ls_R_factor_gt           0.0597
_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^)+(0.0963P)^2^+0.5790P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1636
_refine_ls_wR_factor_ref         0.1764
_reflns_Friedel_coverage         0.711
_reflns_Friedel_fraction_full    0.999
_reflns_Friedel_fraction_max     0.997
_reflns_number_gt                3746
_reflns_number_total             4616
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d3ce00094j2.cif
_cod_data_source_block           srt_(d)-tart
_cod_depositor_comments
'Adding full bibliography for 7246240--7246241.cif.'
_cod_database_code               7246241
_shelx_shelxl_version_number     2014/7
_shelx_estimated_absorpt_t_max   0.898
_shelx_estimated_absorpt_t_min   0.569
_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, All O(H,H) groups
2.a Free rotating group:
 OW2(HW2A,HW2B), OW1(HW1A,HW1B)
2.b Ternary CH refined with riding coordinates:
 C20(H20), C19(H19), C2(H2), C5(H5)
2.c Secondary CH2 refined with riding coordinates:
 N1(H1A,H1B), C4(H4A,H4B), C3(H3A,H3B)
2.d Aromatic/amide H refined with riding coordinates:
 C10(H10), C14(H14), C17(H17), C7(H7), C13(H13), C9(H9), C8(H8)
2.e Tetrahedral OH refined with riding coordinates:
 O6(H6)
2.f Idealised Me refined as rotating group:
 C1(H1C,H1D,H1E)
2.g Idealised tetrahedral OH refined as rotating group:
 O3(H3), O4(H4)
;
_shelx_res_checksum              35361
_shelx_hkl_checksum              78505
_olex2_submission_special_instructions 'No special instructions were received'