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_7155652
_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 Br F3 N3 O7 S'
_chemical_formula_sum            'C24 H17 Br F3 N3 O7 S'
_chemical_formula_weight         628.38
_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            8
_cell_length_a                   9.9489(7)
_cell_length_b                   10.0773(5)
_cell_length_c                   51.389(3)
_cell_measurement_reflns_used    1730
_cell_measurement_temperature    292.65(16)
_cell_measurement_theta_max      25.4660
_cell_measurement_theta_min      3.7800
_cell_volume                     5152.2(5)
_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      292.65(16)
_diffrn_detector_area_resol_mean 16.0733
_diffrn_measured_fraction_theta_full 0.9526
_diffrn_measured_fraction_theta_max 0.6752
_diffrn_measurement_details
;
  1 omega   44.00   69.50   0.7500   10.0000
omega____ theta____ kappa____ phi______ frames
    -       22.7867  178.0000  150.0000 34

  2 omega  -43.00   51.50   0.7500   10.0000
omega____ theta____ kappa____ phi______ frames
    -       22.7867  -38.0000 -180.0000 126
;
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, Eos'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_UB_11      -0.0680025000
_diffrn_orient_matrix_UB_12      0.0211871000
_diffrn_orient_matrix_UB_13      0.0001865000
_diffrn_orient_matrix_UB_21      0.0188236000
_diffrn_orient_matrix_UB_22      0.0572808000
_diffrn_orient_matrix_UB_23      0.0071391000
_diffrn_orient_matrix_UB_31      0.0102973000
_diffrn_orient_matrix_UB_32      0.0349775000
_diffrn_orient_matrix_UB_33      -0.0118102000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.7107
_diffrn_reflns_av_R_equivalents  0.0508
_diffrn_reflns_av_unetI/netI     0.1123
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       28
_diffrn_reflns_limit_l_min       -63
_diffrn_reflns_number            10558
_diffrn_reflns_theta_full        25.50
_diffrn_reflns_theta_max         26.02
_diffrn_reflns_theta_min         3.45
_diffrn_source                   'SuperNova (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    1.748
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.65328
_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    1.620
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             2528
_exptl_crystal_size_max          0.22
_exptl_crystal_size_mid          0.21
_exptl_crystal_size_min          0.14
_refine_diff_density_max         0.327
_refine_diff_density_min         -0.469
_refine_diff_density_rms         0.078
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0.000(15)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.053
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     698
_refine_ls_number_reflns         7979
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.053
_refine_ls_R_factor_all          0.1158
_refine_ls_R_factor_gt           0.0683
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.0263P)^2^+4.8595P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1196
_refine_ls_wR_factor_ref         0.1490
_reflns_number_gt                4896
_reflns_number_total             7979
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            c7ob01013c2.cif
_cod_data_source_block           zhuyy_0113_2
_cod_database_code               7155652
_reflns_odcompleteness_completeness 95.26
_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:
 C9(H9), C10(H10), C11(H11), C33(H33), C34(H34), C35(H35)
2.b Secondary CH2 refined with riding coordinates:
 C8(H8A,H8B), C32(H32A,H32B)
2.c Aromatic/amide H refined with riding coordinates:
 C1(H1), C2(H2), C4(H4), C5(H5), C13(H13), C14(H14), C15(H15), C16(H16),
 C20(H20), C21(H21), C23(H23), C24(H24), C25(H25), C26(H26), C28(H28), C29(H29),
  C37(H37), C38(H38), C39(H39), C40(H40), C43(H43), C44(H44), C46(H46), C47(H47)
;
_olex2_date_sample_data_collection 2017-01-13
_olex2_submission_special_instructions 'No special instructions were received'