Catalytic atroposelective dynamic kinetic resolutions and kinetic resolutions towards 3-arylquinolines <i>via</i> S<sub>N</sub>Ar.
Cardenas, Mariel M.; Saputra, Mirza A.; Gordon, Deane A.; Sanchez, Andrea N.; Yamamoto, Nobuyuki; Gustafson, Jeffrey L.; Chemical communications (Cambridge, England) 57 (2021) 10087–10090; doi:10.1039/d1cc04335h

data_7128941
_publ_section_title
;
 Catalytic atroposelective dynamic kinetic resolutions and kinetic
 resolutions towards 3-arylquinolines <i>via</i> S<sub>N</sub>Ar.
;
_journal_issue                   78
_journal_name_full
'Chemical communications (Cambridge, England)'
_journal_page_first              10087
_journal_page_last               10090
_journal_paper_doi               10.1039/d1cc04335h
_journal_volume                  57
_journal_year                    2021
_chemical_absolute_configuration ad
_chemical_formula_moiety         'C23 H15 F4 N S'
_chemical_formula_sum            'C23 H15 F4 N S'
_chemical_formula_weight         413.42
_chemical_name_systematic
3-(2-fluoro-5-(trifluoromethyl)phenyl)-4-methyl-2-(phenylthio)quinoline
_chemical_properties_physical    Heat-sensitive
_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     direct
_audit_creation_date             2020-04-24
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_audit_update_record
;
2020-04-25 deposited with the CCDC.	2021-09-06 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   9.8999(2)
_cell_length_b                   13.7881(3)
_cell_length_c                   27.3121(6)
_cell_measurement_reflns_used    9999
_cell_measurement_temperature    100
_cell_measurement_theta_max      31.85
_cell_measurement_theta_min      2.54
_cell_volume                     3728.12(14)
_computing_cell_refinement       'SAINT V8.38A (?, 2016)'
_computing_data_reduction        'SAINT V8.38A (?, 2016)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'XL (Sheldrick, 2008)'
_computing_structure_solution    'XS (Sheldrick, 2008)'
_diffrn_ambient_temperature      100
_diffrn_detector                 MoK\a
_diffrn_detector_type            graphite
_diffrn_measured_fraction_theta_full 0.996
_diffrn_measured_fraction_theta_max 0.997
_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  0.0343
_diffrn_reflns_av_unetI/netI     0.0153
_diffrn_reflns_Laue_measured_fraction_full 0.996
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_l_max       35
_diffrn_reflns_limit_l_min       -35
_diffrn_reflns_number            86653
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.101
_diffrn_reflns_theta_min         2.940
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.221
_exptl_absorpt_correction_T_max  0.9282
_exptl_absorpt_correction_T_min  0.8450
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
'SADABS-2016/2 (Bruker,2016/2) was used for absorption correction. wR2(int) was 0.0662 before and 0.0612 after correction. The Ratio of minimum to maximum transmission is 0.9104. The \l/2 correction factor is Not present.'
_exptl_crystal_colour            'clear colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.473
_exptl_crystal_description       block
_exptl_crystal_F_000             1696
_exptl_crystal_recrystallization_method 'Re-crystallisation from solvent'
_exptl_crystal_size_max          0.38
_exptl_crystal_size_mid          0.36
_exptl_crystal_size_min          0.32
_refine_diff_density_max         0.236
_refine_diff_density_min         -0.197
_refine_diff_density_rms         0.036
_refine_ls_abs_structure_details
;
 Refined as an inversion twin.
;
_refine_ls_abs_structure_Flack   -0.03(4)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.058
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     546
_refine_ls_number_reflns         8217
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.058
_refine_ls_R_factor_all          0.0226
_refine_ls_R_factor_gt           0.0223
_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^)+(0.0329P)^2^+0.8626P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0591
_refine_ls_wR_factor_ref         0.0594
_reflns_Friedel_coverage         0.790
_reflns_Friedel_fraction_full    1.000
_reflns_Friedel_fraction_max     1.000
_reflns_number_gt                8110
_reflns_number_total             8217
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d1cc04335h2.cif
_cod_data_source_block           mmc_07_124a_0m
_cod_depositor_comments
'Adding full bibliography for 7128940--7128941.cif.'
_cod_database_code               7128941
_shelx_shelxl_version_number     2017/1
_shelx_estimated_absorpt_t_max   0.933
_shelx_estimated_absorpt_t_min   0.921
_olex2_refinement_description
;
1. Twinned data refinement
 Scales: 1.03(4)
 -0.03(4)
2. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
3. Others
 Sof(F7A)=1-FVAR(1)
 Sof(F7)=FVAR(1)
 Sof(F6A)=1-FVAR(2)
 Sof(F6)=FVAR(2)
4.a Aromatic/amide H refined with riding coordinates:
 C40(H40), C29(H29), C47(H47), C22(H22), C6(H6), C7(H7), C37(H37), C31(H31),
 C15(H15), C8(H8), C38(H38), C17(H17), C46(H46), C30(H30), C20(H20), C24(H24),
 C14(H14), C43(H43), C44(H44), C23(H23), C32(H32), C45(H45), C21(H21), C9(H9)
4.b Idealised Me refined as rotating group:
 C11(H11A,H11B,H11C), C34(H34A,H34B,H34C)
;
_shelx_res_checksum              38660
_olex2_date_sample_completion    2020-02-16
_olex2_date_sample_data_collection 2020-02-11
_olex2_date_sample_submission    2020-02-11
_olex2_submission_special_instructions 'No special instructions were received'