Asymmetric Synthesis of CF3-Containing Tetrahydroquinoline via Thiourea-Catalyzed Cascade Reaction
Zhu, Yuanyuan; Li, Boyu; Wang, Cui; Dong, Zhenghao; Zhong, Xiaoling; Wang, Kairong; Yan, Wenjin; Wang, Rui; Org. Biomol. Chem.  (2017) –; doi:10.1039/C7OB01013C

data_7155651
_publ_section_title
;
 Asymmetric Synthesis of CF3-Containing Tetrahydroquinoline via
 Thiourea-Catalyzed Cascade Reaction
;
_journal_name_full               'Org. Biomol. Chem.'
_journal_paper_doi               10.1039/C7OB01013C
_journal_year                    2017
_chemical_absolute_configuration ad
_chemical_formula_moiety         'C24 H17 Cl F3 N3 O7 S'
_chemical_formula_sum            'C24 H17 Cl F3 N3 O7 S'
_chemical_formula_weight         583.92
_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   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_date             2017-01-13
_audit_creation_method
;
Olex2 1.2
(compiled 2016.11.30 svn.r3356 for OlexSys, GUI svn.r5269)
;
_audit_update_record
;
2017-03-03 deposited with the CCDC.
2017-05-18 downloaded from the CCDC.
;
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   9.6118(5)
_cell_length_b                   9.9839(5)
_cell_length_c                   26.2874(14)
_cell_measurement_reflns_used    1625
_cell_measurement_temperature    293.00(10)
_cell_measurement_theta_max      25.6450
_cell_measurement_theta_min      3.7470
_cell_volume                     2522.6(2)
_computing_cell_refinement
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET)
(compiled Feb  1 2013,16:14:44)
;
_computing_data_collection
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET)
(compiled Feb  1 2013,16:14:44)
;
_computing_data_reduction
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET)
(compiled Feb  1 2013,16:14:44)
;
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXS (Sheldrick, 2008)'
_diffrn_ambient_temperature      293.00(10)
_diffrn_detector_area_resol_mean 16.0733
_diffrn_measured_fraction_theta_full 0.9939
_diffrn_measured_fraction_theta_max 0.7469
_diffrn_measurement_details
;
  1 omega   37.00   84.00   1.0000    6.0000
omega____ theta____ kappa____ phi______ frames
    -       22.7867  178.0000 -180.0000 47

  2 omega   70.00  105.00   1.0000    6.0000
omega____ theta____ kappa____ phi______ frames
    -       22.7867 -178.0000  -90.0000 35

  3 omega  -20.00   41.00   1.0000    6.0000
omega____ theta____ kappa____ phi______ frames
    -       22.7867  -99.0000    0.0000 61
;
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, Eos'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_UB_11      -0.0698304000
_diffrn_orient_matrix_UB_12      0.0181369000
_diffrn_orient_matrix_UB_13      -0.0054453000
_diffrn_orient_matrix_UB_21      -0.0105258000
_diffrn_orient_matrix_UB_22      -0.0630781000
_diffrn_orient_matrix_UB_23      -0.0118829000
_diffrn_orient_matrix_UB_31      -0.0215747000
_diffrn_orient_matrix_UB_32      -0.0274046000
_diffrn_orient_matrix_UB_33      0.0235503000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.7107
_diffrn_reflns_av_R_equivalents  0.0235
_diffrn_reflns_av_unetI/netI     0.0509
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       32
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            6105
_diffrn_reflns_theta_full        26.02
_diffrn_reflns_theta_max         26.02
_diffrn_reflns_theta_min         3.71
_diffrn_source                   'SuperNova (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    0.307
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.43640
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET)
(compiled Feb  1 2013,16:14:44)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_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    1.537
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             1192
_exptl_crystal_size_max          0.21
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.14
_refine_diff_density_max         0.195
_refine_diff_density_min         -0.228
_refine_diff_density_rms         0.046
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0.06(9)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.062
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     352
_refine_ls_number_reflns         4290
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.062
_refine_ls_R_factor_all          0.0664
_refine_ls_R_factor_gt           0.0486
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.0394P)^2^+0.2110P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0949
_refine_ls_wR_factor_ref         0.1086
_reflns_number_gt                3385
_reflns_number_total             4290
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            c7ob01013c2.cif
_cod_data_source_block           zhuyy_0113_1
_cod_database_code               7155651
_reflns_odcompleteness_completeness 99.39
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     26.32
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
2.a Ternary CH refined with riding coordinates:
 C1(H1), C2(H2), C3(H3)
2.b Secondary CH2 refined with riding coordinates:
 C10(H10A,H10B)
2.c Aromatic/amide H refined with riding coordinates:
 C6(H6), C8(H8), C9(H9), C13(H13), C14(H14), C15(H15), C16(H16), C17(H17),
 C20(H20), C21(H21), C23(H23), C24(H24)
;
_olex2_date_sample_data_collection 2017-01-13
_olex2_submission_special_instructions 'No special instructions were received'