Synthesis of Chiral Bis(3-indolyl)methanes Bearing a Trifluoromethylated All-Carbon Quaternary Stereocenter via Nickel-Catalyzed Asymmetric Friedel-Crafts Alkylation Reaction.
Zhu, Wen-Jing; Gong, Jun-Fang; Song, Mao-Ping; The Journal of organic chemistry  (2020) –; doi:10.1021/acs.joc.0c00336

data_4038591
_publ_section_title
;
 Synthesis of Chiral Bis(3-indolyl)methanes Bearing a Trifluoromethylated
 All-Carbon Quaternary Stereocenter via Nickel-Catalyzed Asymmetric
 Friedel-Crafts Alkylation Reaction.
;
_journal_name_full               'The Journal of organic chemistry'
_journal_paper_doi               10.1021/acs.joc.0c00336
_journal_year                    2020
_chemical_absolute_configuration ad
_chemical_formula_moiety         'C27 H22 F3 N3 O5 S'
_chemical_formula_sum            'C27 H22 F3 N3 O5 S'
_chemical_formula_weight         557.53
_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   mixed
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Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
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_cell_measurement_temperature    293(2)
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_cell_measurement_theta_min      4.6190
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_computing_cell_refinement
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CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
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_computing_data_collection
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CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
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CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
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_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
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  1 omega  -91.00  -51.00   1.0000    1.4000
omega____ theta____ kappa____ phi______ frames
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  2 omega -108.00  -34.00   1.0000    1.4000
omega____ theta____ kappa____ phi______ frames
    -      -33.5000  178.0000  120.0000 74

  3 omega   65.00  109.00   1.0000    1.4000
omega____ theta____ kappa____ phi______ frames
    -       36.4734  178.0000 -120.0000 44

  4 omega  -34.00   -6.00   1.0000    1.4000
omega____ theta____ kappa____ phi______ frames
    -       36.4734    0.0000 -180.0000 28

  5 omega   68.00   94.00   1.0000    1.4000
omega____ theta____ kappa____ phi______ frames
    -       36.4734  178.0000 -180.0000 26

  6 omega   22.00   99.00   1.0000    1.4000
omega____ theta____ kappa____ phi______ frames
    -       36.4734   57.0000  150.0000 77

  7 omega    9.00   35.00   1.0000    1.4000
omega____ theta____ kappa____ phi______ frames
    -       36.4734    0.0000 -180.0000 26

  8 omega   58.00  105.00   1.0000    1.4000
omega____ theta____ kappa____ phi______ frames
    -       36.4734  178.0000  150.0000 47

  9 omega   64.00  110.00   1.0000    1.4000
omega____ theta____ kappa____ phi______ frames
    -       36.4734  178.0000    0.0000 46

 10 omega   47.00   92.00   1.0000    9.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -45.0000 -120.0000 45

 11 omega   78.00  108.00   1.0000    9.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000 -111.0000 -150.0000 30

 12 omega   40.00   74.00   1.0000    9.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000 -111.0000 -150.0000 34

 13 omega   47.00  104.00   1.0000    9.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -94.0000   60.0000 57

 14 omega   50.00   86.00   1.0000    9.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -45.0000   30.0000 36

 15 omega   38.00   95.00   1.0000    9.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -45.0000   90.0000 57

 16 omega   71.00  109.00   1.0000    9.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -94.0000 -120.0000 38

 17 omega   61.00  128.00   1.0000    9.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -61.0000  150.0000 67

 18 omega   40.00   88.00   1.0000    9.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -30.0000  -60.0000 48

 19 omega  110.00  173.00   1.0000    9.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000   45.0000  -90.0000 63
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_diffrn_measurement_device       'four-circle diffractometer'
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_diffrn_orient_matrix_UB_11      -0.0530855000
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_diffrn_orient_matrix_UB_21      -0.0362615000
_diffrn_orient_matrix_UB_22      0.1385045000
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_diffrn_orient_matrix_UB_31      -0.1379619000
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_diffrn_orient_matrix_UB_33      -0.0178539000
_diffrn_radiation_monochromator  graphite
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_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
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_diffrn_reflns_av_unetI/netI     0.0429
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_diffrn_reflns_limit_h_min       -12
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_diffrn_reflns_limit_l_min       -28
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_diffrn_reflns_point_group_measured_fraction_full 0.981
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_diffrn_reflns_theta_full        67.055
_diffrn_reflns_theta_max         67.055
_diffrn_reflns_theta_min         3.647
_diffrn_source                   'Enhance (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    1.722
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.79963
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
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CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
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_exptl_crystal_colour            colourless
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_exptl_crystal_size_mid          0.15
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_refine_ls_abs_structure_details
;
 Flack x determined using 1400 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.002(14)
_refine_ls_extinction_method     none
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_refine_ls_matrix_type           full
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'w=1/[\s^2^(Fo^2^)+(0.1000P)^2^] where P=(Fo^2^+2Fc^2^)/3'
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_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            jo0c00336_si_002.cif
_cod_data_source_block           201906166
_cod_database_code               4038591
_shelx_shelxl_version_number     2014/7
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_reflns_odcompleteness_iscentric 1
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_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 Secondary CH2 refined with riding coordinates:
 C11(H11A,H11B)
2.b Aromatic/amide H refined with riding coordinates:
 C1(H1), C2(H2), C3(H3), C4(H4), C8(H8), C12(H12), C16(H16), C18(H18),
 C19(H19), C22(H22), C23(H23), C25(H25), C26(H26)
2.c Idealised Me refined as rotating group:
 C20(H20A,H20B,H20C), C27(H27A,H27B,H27C)
;
_olex2_submission_special_instructions 'No special instructions were received'