Chiral phosphoric acid-catalyzed asymmetric transfer hydrogenation of 3-trifluoromethylthioquinolines.
Zhou, Ji; Zhang, Qian-Fan; Zhao, Wei-Hao; Jiang, Guo-Fang; Organic & biomolecular chemistry 14 (2016) 6937–6941; doi:10.1039/c6ob01176d

data_7155169
_publ_section_title
;
 Chiral phosphoric acid-catalyzed asymmetric transfer hydrogenation of
 3-trifluoromethylthioquinolines.
;
_journal_issue                   29
_journal_name_full               'Organic &amp; biomolecular chemistry'
_journal_page_first              6937
_journal_page_last               6941
_journal_paper_doi               10.1039/c6ob01176d
_journal_volume                  14
_journal_year                    2016
_chemical_absolute_configuration ad
_chemical_formula_sum            'C17 H16 F3 N S'
_chemical_formula_weight         323.37
_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'
_symmetry_space_group_name_Hall  'P 2ac 2ab'
_symmetry_space_group_name_H-M   'P 21 21 21'
_atom_sites_solution_hydrogens   mixed
_audit_creation_method           SHELXL-2013
_audit_update_record
;
2015-11-27 deposited with the CCDC.
2016-06-17 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   9.8932(13)
_cell_length_b                   15.009(2)
_cell_length_c                   21.270(3)
_cell_measurement_reflns_used    2698
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      40.524
_cell_measurement_theta_min      4.541
_cell_volume                     3158.3(7)
_computing_cell_refinement       'Bruker SMART'
_computing_data_collection       'Bruker SMART'
_computing_data_reduction        'Bruker SHELXTL'
_computing_molecular_graphics    'Bruker SHELXTL'
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_computing_structure_solution    'Bruker SHELXTL'
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_diffrn_measured_fraction_theta_max 1.000
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_diffrn_measurement_method       'phi and omega scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0582
_diffrn_reflns_av_unetI/netI     0.0597
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_k_min       -18
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_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            18275
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 1.000
_diffrn_reflns_theta_full        25.242
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_diffrn_reflns_theta_min         1.661
_exptl_absorpt_coefficient_mu    0.231
_exptl_absorpt_correction_T_max  0.7456
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_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   sadabs
_exptl_crystal_colour            colorless
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_exptl_crystal_F_000             1344
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_exptl_crystal_size_mid          0.140
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_refine_ls_abs_structure_details
; 
 Flack x determined using 1541 quotients [(I+)-(I-)]/[(I+)+(I-)] 
 (Parsons and Flack (2004), Acta Cryst. A60, s61). 
;
_refine_ls_abs_structure_Flack   -0.01(5)
_refine_ls_extinction_method     none
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_refine_ls_number_reflns         5871
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.034
_refine_ls_R_factor_all          0.0720
_refine_ls_R_factor_gt           0.0539
_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^)+(0.0540P)^2^+0.0065P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1106
_refine_ls_wR_factor_ref         0.1186
_reflns_Friedel_coverage         0.773
_reflns_Friedel_fraction_full    1.000
_reflns_Friedel_fraction_max     1.000
_reflns_number_gt                4591
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_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c6ob01176d2.cif
_cod_data_source_block           cd15290
_cod_depositor_comments          'Adding full bibliography for 7155169.cif.'
_cod_original_cell_volume        3158.2(7)
_cod_database_code               7155169
_shelx_estimated_absorpt_t_min   0.951
_shelx_estimated_absorpt_t_max   0.977
_shelxl_version_number           2013-4
_shelx_res_checksum              3664