Chiral Selenide-Catalyzed Enantioselective Construction of Saturated Trifluoromethylthiolated Azaheterocycles
Luo, Jie; Liu, Yannan; Zhao, Xiaodan; Organic Letters  (2017) –; doi:10.1021/acs.orglett.7b01392

data_1546354
_publ_section_title
;
 Chiral Selenide-Catalyzed Enantioselective Construction of Saturated
 Trifluoromethylthiolated Azaheterocycles
;
_journal_name_full               'Organic Letters'
_journal_paper_doi               10.1021/acs.orglett.7b01392
_journal_year                    2017
_chemical_absolute_configuration unk
_chemical_formula_moiety         'C13 H15 F3 N2 O4 S2'
_chemical_formula_sum            'C13 H15 F3 N2 O4 S2'
_chemical_formula_weight         384.40
_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_Int_Tables_number      19
_symmetry_space_group_name_Hall  'P 2ac 2ab'
_symmetry_space_group_name_H-M   'P 21 21 21'
_atom_sites_solution_primary     iterative
_audit_creation_date             2017-03-22
_audit_creation_method
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Olex2 1.2
(compiled 2017.01.04 svn.r3372 for OlexSys, GUI svn.r5292)
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_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   6.3432(2)
_cell_length_b                   12.8646(6)
_cell_length_c                   20.0976(8)
_cell_measurement_reflns_used    1955
_cell_measurement_temperature    298
_cell_measurement_theta_max      23.4760
_cell_measurement_theta_min      3.4320
_cell_volume                     1640.02(11)
_computing_cell_refinement
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CrysAlisPro, Agilent Technologies,
Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET)
(compiled Feb  1 2013,16:14:44)
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_computing_data_collection
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CrysAlisPro, Agilent Technologies,
Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET)
(compiled Feb  1 2013,16:14:44)
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_computing_data_reduction
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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  'olex2.refine (Bourhis et al., 2015)'
_computing_structure_solution    'olex2.solve (Bourhis et al., 2015)'
_diffrn_ambient_temperature      298
_diffrn_detector_area_resol_mean 16.0855
_diffrn_measured_fraction_theta_full 0.9979
_diffrn_measured_fraction_theta_max 0.9979
_diffrn_measurement_details
;
  1 omega  -13.00   51.00   1.0000   70.0000
omega____ theta____ kappa____ phi______ frames
    -      -18.0610   57.0000  120.0000 64

  2 omega  -87.00  -12.00   1.0000   70.0000
omega____ theta____ kappa____ phi______ frames
    -      -18.0610  -57.0000  150.0000 75

  3 omega   56.00   83.00   1.0000   70.0000
omega____ theta____ kappa____ phi______ frames
    -       18.0610 -138.0000  -16.0000 27

  4 omega    5.00   49.00   1.0000   70.0000
omega____ theta____ kappa____ phi______ frames
    -       18.0610  -99.0000  -30.0000 44
;
_diffrn_measurement_device_type  'Xcalibur, Sapphire3, Gemini ultra'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_UB_11      0.1082986000
_diffrn_orient_matrix_UB_12      0.0137049000
_diffrn_orient_matrix_UB_13      0.0002704000
_diffrn_orient_matrix_UB_21      0.0277288000
_diffrn_orient_matrix_UB_22      -0.0532366000
_diffrn_orient_matrix_UB_23      0.0027315000
_diffrn_orient_matrix_UB_31      0.0029992000
_diffrn_orient_matrix_UB_32      -0.0040654000
_diffrn_orient_matrix_UB_33      -0.0351908000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0310
_diffrn_reflns_av_unetI/netI     0.0520
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_l_max       26
_diffrn_reflns_limit_l_min       -25
_diffrn_reflns_number            6702
_diffrn_reflns_theta_full        24.9924
_diffrn_reflns_theta_max         24.99
_diffrn_reflns_theta_min         3.17
_diffrn_source                   'Enhance (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    0.377
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.86956
_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            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.5567
_exptl_crystal_description       block
_exptl_crystal_F_000             793.5209
_exptl_crystal_size_max          0.05
_exptl_crystal_size_mid          0.04
_exptl_crystal_size_min          0.04
_refine_diff_density_max         0.3027
_refine_diff_density_min         -0.2640
_refine_diff_density_rms         0.0613
_refine_ls_abs_structure_details
'Flack, H. D. (1983). Acta Cryst. A39, 876-881.'
_refine_ls_abs_structure_Flack   0.18(14)
_refine_ls_d_res_high            0.8411
_refine_ls_d_res_low             6.4323
_refine_ls_goodness_of_fit_ref   1.0667
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_constraints    25
_refine_ls_number_parameters     217
_refine_ls_number_reflns         2891
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.0667
_refine_ls_R_factor_all          0.0568
_refine_ls_R_factor_gt           0.0488
_refine_ls_shift/su_max          0.0000
_refine_ls_shift/su_mean         0.0000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0590P)^2^+0.2280P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1125
_refine_ls_wR_factor_ref         0.1172
_reflns_Friedel_coverage         0.999
_reflns_limit_h_max              7
_reflns_limit_h_min              -7
_reflns_limit_k_max              15
_reflns_limit_k_min              -15
_reflns_limit_l_max              23
_reflns_limit_l_min              -23
_reflns_number_gt                2579
_reflns_number_total             2891
_reflns_threshold_expression     I>=2u(I)
_cod_data_source_file            ol7b01392_si_003.cif
_cod_data_source_block           exp_21168
_cod_original_sg_symbol_Hall     ' P 2ac 2ab'
_cod_database_code               1546354
_reflns_odcompleteness_completeness 99.54
_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
 At 1.5 times of:
  All C(H,H,H) groups
2.a Ternary CH refined with riding coordinates:
 C13(H13), C14(H14)
2.b Secondary CH2 refined with riding coordinates:
 C19(H19a,H19b), C20(H20a,H20b), C23(H23a,H23b)
2.c Aromatic/amide H refined with riding coordinates:
 C5(H5), C9(H9), C16(H16), C17(H17)
2.d Idealised Me refined as rotating group:
 C15(H15a,H15b,H15c)
;
_olex2_submission_special_instructions 'No special instructions were received'