Construction of Furan Derivatives with a Trifluoromethyl Stereogenic Center: Enantioselective Friedel-Crafts Alkylations via Formal Trienamine Catalysis.
Yang, Guang-Jun; Du, Wei; Chen, Ying-Chun; The Journal of organic chemistry 81 (2016) 10056–10061; doi:10.1021/acs.joc.6b01950

data_4037308
_publ_section_title
;
 Construction of Furan Derivatives with a Trifluoromethyl Stereogenic
 Center: Enantioselective Friedel-Crafts Alkylations via Formal Trienamine
 Catalysis.
;
_journal_issue                   20
_journal_name_full               'The Journal of organic chemistry'
_journal_page_first              10056
_journal_page_last               10061
_journal_paper_doi               10.1021/acs.joc.6b01950
_journal_volume                  81
_journal_year                    2016
_chemical_absolute_configuration rm
_chemical_formula_moiety         'C19 H17 F3 O3'
_chemical_formula_sum            'C19 H17 F3 O3'
_chemical_formula_weight         350.32
_space_group_crystal_system      monoclinic
_space_group_IT_number           4
_space_group_name_Hall           'P 2yb'
_space_group_name_H-M_alt        'P 1 21 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_audit_creation_date             2015-09-13
_audit_creation_method
;
Olex2 1.2
(compiled 2014.07.22 svn.r2960 for OlexSys, GUI svn.r4862)
;
_cell_angle_alpha                90
_cell_angle_beta                 91.3092(16)
_cell_angle_gamma                90
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_cell_length_a                   12.5614(2)
_cell_length_b                   5.24978(10)
_cell_length_c                   13.4122(3)
_cell_measurement_reflns_used    6648
_cell_measurement_temperature    290.70(10)
_cell_measurement_theta_max      71.1290
_cell_measurement_theta_min      4.7530
_cell_volume                     884.23(3)
_computing_cell_refinement
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
;
_computing_data_collection
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
;
_computing_data_reduction
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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)
;
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
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;
  1 omega   20.00  104.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       36.7203   57.0000 -120.0000 84

  2 omega   18.00  106.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
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  3 omega   57.00  109.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       36.7203  178.0000   60.0000 52

  4 omega   57.00  109.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       36.7203  178.0000   30.0000 52

  5 omega   20.00  104.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       36.7203   57.0000   60.0000 84

  6 omega    1.00   76.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       36.7203  -99.0000 -180.0000 75

  7 omega   39.00  110.00   1.0000    5.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -95.0000  -90.0000 71

  8 omega   38.00   91.00   1.0000    5.0000
omega____ theta____ kappa____ phi______ frames
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  9 omega   41.00  126.00   1.0000    5.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -61.0000 -150.0000 85

 10 omega   38.00   91.00   1.0000    5.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -30.0000 -180.0000 53

 11 omega   40.00   98.00   1.0000    5.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -45.0000   30.0000 58

 12 omega   40.00   98.00   1.0000    5.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -45.0000  120.0000 58

 13 omega   87.00  178.00   1.0000    5.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000   30.0000    0.0000 91

 14 omega   39.00  110.00   1.0000    5.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -95.0000  150.0000 71

 15 omega   38.00   91.00   1.0000    5.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -30.0000   60.0000 53

 16 omega  -35.00   66.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       36.7203  -19.0000  -60.0000 101

 17 omega  -35.00   66.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       36.7203  -19.0000 -180.0000 101

 18 omega   20.00  104.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       36.7203   57.0000  -30.0000 84

 19 omega   10.00  104.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       36.7203   77.0000   60.0000 94

 20 omega  -31.00   53.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       36.7203  -57.0000   90.0000 84

 21 omega   55.00  109.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       36.7203 -178.0000  150.0000 54

 22 omega   70.00  178.00   1.0000    5.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000   15.0000 -150.0000 108

 23 omega   91.00  176.00   1.0000    5.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000   45.0000  120.0000 85

 24 omega   39.00  110.00   1.0000    5.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -95.0000   60.0000 71

 25 omega   87.00  178.00   1.0000    5.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000   30.0000  -90.0000 91

 26 omega   87.00  178.00   1.0000    5.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000   30.0000   90.0000 91

 27 omega   40.00   98.00   1.0000    5.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -45.0000  -60.0000 58

 28 omega   10.00  104.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       36.7203   77.0000  -90.0000 94

 29 omega   20.00  104.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       36.7203   57.0000 -180.0000 84

 30 omega    1.00   60.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       36.7203  -99.0000  -60.0000 59

 31 omega   10.00  104.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       36.7203   77.0000  -30.0000 94
;
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_diffrn_orient_matrix_UB_13      -0.1087843000
_diffrn_orient_matrix_UB_21      -0.1121708000
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_diffrn_orient_matrix_UB_33      -0.0341694000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0302
_diffrn_reflns_av_unetI/netI     0.0210
_diffrn_reflns_Laue_measured_fraction_full 0.998
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_diffrn_reflns_limit_h_max       15
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_diffrn_reflns_limit_k_max       6
_diffrn_reflns_limit_k_min       -5
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_diffrn_reflns_limit_l_min       -16
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_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         71.284
_diffrn_reflns_theta_min         4.769
_diffrn_source                   'sealed X-ray tube'
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_exptl_absorpt_process_details
;
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.
;
_exptl_crystal_colour            'clear light colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
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_exptl_crystal_density_diffrn    1.316
_exptl_crystal_description       block
_exptl_crystal_F_000             364
_exptl_crystal_size_max          0.13
_exptl_crystal_size_mid          0.12
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_refine_diff_density_min         -0.173
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_refine_ls_abs_structure_details
;
 Flack x determined using 1126 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.04(9)
_refine_ls_extinction_method     none
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_refine_ls_matrix_type           full
_refine_ls_number_parameters     227
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_refine_ls_restrained_S_all      1.047
_refine_ls_R_factor_all          0.0481
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_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0815P)^2^+0.1200P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
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_reflns_number_gt                2983
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_cod_data_source_file            jo6b01950_si_002.cif
_cod_data_source_block           3m
_cod_database_code               4037308
_shelxl_version_number           2014-1
_chemical_oxdiff_formula         'C1 H1 O1 F1'
_reflns_odcompleteness_completeness 99.83
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.97
_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:
 C11(H11)
2.b Secondary CH2 refined with riding coordinates:
 C10(H10A,H10B), C22(H22A,H22B)
2.c Aromatic/amide H refined with riding coordinates:
 C20(H20), C19(H19), C8(H8), C7(H7), C2(H2), C4(H4), C6(H6), C3(H3), C5(H5)
2.d Idealised Me refined as rotating group:
 C25(H25A,H25B,H25C)
;
_shelx_res_checksum              29942
_shelx_hkl_checksum              26383
_olex2_submission_special_instructions 'No special instructions were received'