Highly Enantioselective Copper-Catalyzed Electrophilic Trifluoromethylation of β-Ketoesters
Qing-Hai Deng; Hubert Wadepohl; Lutz H. Gade; Journal of the American Chemical Society 134 (2012) 10769–10772; doi:10.1021/ja3039773

data_4118185
_publ_section_title
;
 Highly Enantioselective Copper-Catalyzed Electrophilic
 Trifluoromethylation of \b-Ketoesters
;
_journal_name_full               'Journal of the American Chemical Society'
_journal_page_first              10769
_journal_page_last               10772
_journal_paper_doi               10.1021/ja3039773
_journal_volume                  134
_journal_year                    2012
_chemical_formula_sum            'C20 H25 F3 O3'
_chemical_formula_weight         370.40
_space_group_IT_number           2
_symmetry_cell_setting           triclinic
_symmetry_Int_Tables_number      2
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -1'
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     iterative
_atom_sites_solution_secondary   difmap
_audit_block_code                ga_dq_11
_audit_creation_date
;
'Wed Apr 18 11:32:03 2012'
;
_audit_creation_method
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CrysAlisPro, Oxford Diffraction Ltd.,
Version 1.171.35.21 (release 20-01-2012 CrysAlis171 .NET)
(compiled Jan 23 2012,18:06:46)
;
_audit_update_record             'Wed Apr 18 12:26:20 CEST 2012'
_cell_angle_alpha                84.2465(16)
_cell_angle_beta                 66.5081(18)
_cell_angle_gamma                75.4175(17)
_cell_formula_units_Z            2
_cell_length_a                   9.49361(19)
_cell_length_b                   9.58111(20)
_cell_length_c                   11.7944(2)
_cell_measurement_reflns_used    32675
_cell_measurement_temperature    110.00(10)
_cell_measurement_theta_max      71.7527
_cell_measurement_theta_min      4.0836
_cell_volume                     952.20(4)
_computing_cell_refinement
;
CrysAlisPro, Agilent Technologies,
Version 1.171.35.21 (release 20-01-2012 CrysAlis171 .NET)
(compiled Jan 23 2012,18:06:46)
;
_computing_data_collection
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CrysAlisPro, Agilent Technologies,
Version 1.171.35.21 (release 20-01-2012 CrysAlis171 .NET)
(compiled Jan 23 2012,18:06:46)
;
_computing_data_reduction
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CrysAlisPro, Agilent Technologies,
Version 1.171.35.21 (release 20-01-2012 CrysAlis171 .NET)
(compiled Jan 23 2012,18:06:46)
;
_computing_publication_material  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SUPERFLIP (Palatinus, 2007-2009)'
_diffrn_ambient_temperature      110.00(10)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 7.9621
_diffrn_detector_type            'Agilent EOS'
_diffrn_measured_fraction_theta_full 0.984
_diffrn_measured_fraction_theta_max 0.976
_diffrn_measurement_details
;
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  5 omega  -56.00   21.00   1.0000    3.0000
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  9 omega -102.00  -76.00   1.0000    3.0000
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 10 omega  -36.00   24.00   1.0000    3.0000
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 11 omega  -40.00  -15.00   1.0000    3.0000
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 12 omega -105.00  -78.00   1.0000    3.0000
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 13 omega -113.00  -87.00   1.0000    3.0000
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 14 omega  -54.00  -13.00   1.0000    3.0000
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 15 omega  -41.00  -16.00   1.0000    3.0000
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 16 omega   17.00   44.00   1.0000    3.0000
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 17 omega   18.00   48.00   1.0000    3.0000
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 18 omega   21.00   47.00   1.0000    3.0000
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 19 omega   19.00   46.00   1.0000    3.0000
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 20 omega   19.00   44.00   1.0000    3.0000
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 21 omega   18.00   45.00   1.0000    3.0000
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 22 omega   19.00   46.00   1.0000    3.0000
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 23 omega   19.00   46.00   1.0000    3.0000
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 24 omega   25.00  113.00   1.0000    3.0000
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 25 omega  -15.00   20.00   1.0000    3.0000
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 26 omega   47.00  122.00   1.0000    3.0000
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 27 omega  -16.00   84.00   1.0000    3.0000
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 28 omega   43.00   78.00   1.0000    3.0000
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 29 omega   60.00   85.00   1.0000    3.0000
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 30 omega    1.00   87.00   1.0000    3.0000
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 31 omega   28.00  127.00   1.0000    3.0000
omega____ theta____ kappa____ phi______ frames
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 32 omega   30.00  117.00   1.0000    3.0000
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 33 omega  120.00  173.00   1.0000    6.0000
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 34 omega  119.00  177.00   1.0000    6.0000
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 35 omega   80.00  106.00   1.0000    6.0000
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 36 omega   92.00  119.00   1.0000    6.0000
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 37 omega   86.00  114.00   1.0000    6.0000
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 38 omega   85.00  115.00   1.0000    6.0000
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 39 omega   80.00  106.00   1.0000    6.0000
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 40 omega  151.00  176.00   1.0000    6.0000
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    -      110.2342   77.0000    0.0000 25

 41 omega   89.00  122.00   1.0000    6.0000
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 42 omega   80.00  105.00   1.0000    6.0000
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 43 omega   49.00  117.00   1.0000    6.0000
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 44 omega   80.00  105.00   1.0000    6.0000
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 45 omega  130.00  169.00   1.0000    6.0000
omega____ theta____ kappa____ phi______ frames
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 46 omega   80.00  106.00   1.0000    6.0000
omega____ theta____ kappa____ phi______ frames
    -      110.2342   77.0000  -60.0000 26

 47 omega   95.00  154.00   1.0000    6.0000
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 48 omega  118.00  175.00   1.0000    6.0000
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 49 omega   85.00  120.00   1.0000    6.0000
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 50 omega   80.00  106.00   1.0000    6.0000
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 51 omega   93.00  146.00   1.0000    6.0000
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 52 omega   86.00  118.00   1.0000    6.0000
omega____ theta____ kappa____ phi______ frames
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 53 omega   85.00  114.00   1.0000    6.0000
omega____ theta____ kappa____ phi______ frames
    -      110.2342   38.0000  120.0000 29

 54 omega   86.00  118.00   1.0000    6.0000
omega____ theta____ kappa____ phi______ frames
    -      110.2342   38.0000  -60.0000 32

 55 omega   87.00  129.00   1.0000    6.0000
omega____ theta____ kappa____ phi______ frames
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 56 omega   93.00  141.00   1.0000    6.0000
omega____ theta____ kappa____ phi______ frames
    -      110.2342   50.0000  150.0000 48

 57 omega   91.00  117.00   1.0000    6.0000
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    -      110.2342   25.0000    0.0000 26

 58 omega   91.00  117.00   1.0000    6.0000
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 59 omega   80.00  105.00   1.0000    6.0000
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 60 omega   93.00  119.00   1.0000    6.0000
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 61 omega   96.00  178.00   1.0000    6.0000
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 62 omega   91.00  177.00   1.0000    6.0000
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 63 omega   92.00  177.00   1.0000    6.0000
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 64 omega   82.00  108.00   1.0000    6.0000
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 65 omega  140.00  167.00   1.0000    6.0000
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 66 omega   80.00  106.00   1.0000    6.0000
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 67 omega   42.00   97.00   1.0000    6.0000
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 69 omega   94.00  122.00   1.0000    6.0000
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 71 omega   88.00  121.00   1.0000    6.0000
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 72 omega   40.00  140.00   1.0000    6.0000
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 73 omega   80.00  106.00   1.0000    6.0000
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 74 omega   89.00  115.00   1.0000    6.0000
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    -      110.2342   63.0000  120.0000 26

 75 omega   89.00  178.00   1.0000    6.0000
omega____ theta____ kappa____ phi______ frames
    -      110.2342   63.0000 -150.0000 89

 76 omega   93.00  121.00   1.0000    6.0000
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 77 omega   93.00  125.00   1.0000    6.0000
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 78 omega   80.00  106.00   1.0000    6.0000
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 80 omega   40.00   98.00   1.0000    6.0000
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 83 omega  125.00  151.00   1.0000    6.0000
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 84 omega   86.00  123.00   1.0000    6.0000
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 85 omega   85.00  112.00   1.0000    6.0000
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 87 omega   88.00  177.00   1.0000    6.0000
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 95 omega -111.00  -21.00   1.0000    3.0000
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 96 omega -113.00  -21.00   1.0000    3.0000
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 97 omega   15.00   49.00   1.0000    3.0000
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 98 omega   15.00   49.00   1.0000    3.0000
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 99 omega   18.00   46.00   1.0000    3.0000
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100 omega   20.00  120.00   1.0000    3.0000
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101 omega   19.00   47.00   1.0000    3.0000
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102 omega   19.00   47.00   1.0000    3.0000
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103 omega   19.00   49.00   1.0000    3.0000
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104 omega   24.00  124.00   1.0000    3.0000
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105 omega  -14.00   77.00   1.0000    3.0000
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106 omega  -16.00   87.00   1.0000    3.0000
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107 omega  -15.00   85.00   1.0000    3.0000
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108 omega  -18.00  128.00   1.0000    3.0000
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109 omega  -18.00  128.00   1.0000    3.0000
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110 omega   25.00  125.00   1.0000    3.0000
omega____ theta____ kappa____ phi______ frames
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111 omega  -18.00  128.00   1.0000    3.0000
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112 omega  -18.00  128.00   1.0000    3.0000
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113 omega  -15.00   85.00   1.0000    3.0000
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114 omega   28.00  124.00   1.0000    3.0000
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115 omega  -15.00   85.00   1.0000    3.0000
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116 omega   28.00  128.00   1.0000    3.0000
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117 omega   30.00  128.00   1.0000    3.0000
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118 omega   37.00  178.00   1.0000    6.0000
omega____ theta____ kappa____ phi______ frames
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119 omega   37.00   94.00   1.0000    6.0000
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120 omega   37.00   94.00   1.0000    6.0000
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121 omega   39.00  142.00   1.0000    6.0000
omega____ theta____ kappa____ phi______ frames
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122 omega   39.00  142.00   1.0000    6.0000
omega____ theta____ kappa____ phi______ frames
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123 omega   80.00  178.00   1.0000    6.0000
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127 omega   88.00  178.00   1.0000    6.0000
omega____ theta____ kappa____ phi______ frames
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128 omega   88.00  178.00   1.0000    6.0000
omega____ theta____ kappa____ phi______ frames
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129 omega   88.00  178.00   1.0000    6.0000
omega____ theta____ kappa____ phi______ frames
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130 omega   88.00  178.00   1.0000    6.0000
omega____ theta____ kappa____ phi______ frames
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131 omega   76.00  178.00   1.0000    6.0000
omega____ theta____ kappa____ phi______ frames
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132 omega   80.00  178.00   1.0000    6.0000
omega____ theta____ kappa____ phi______ frames
    -      110.2342   77.0000  -90.0000 98

133 omega   88.00  178.00   1.0000    6.0000
omega____ theta____ kappa____ phi______ frames
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134 omega   76.00  178.00   1.0000    6.0000
omega____ theta____ kappa____ phi______ frames
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135 omega   80.00  178.00   1.0000    6.0000
omega____ theta____ kappa____ phi______ frames
    -      110.2342   77.0000    0.0000 98

136 omega   80.00  178.00   1.0000    6.0000
omega____ theta____ kappa____ phi______ frames
    -      110.2342   77.0000 -180.0000 98

137 omega   40.00  141.00   1.0000    6.0000
omega____ theta____ kappa____ phi______ frames
    -      110.2342  -79.0000  131.0000 101

138 omega   85.00  178.00   1.0000    6.0000
omega____ theta____ kappa____ phi______ frames
    -      110.2342   38.0000 -180.0000 93

139 omega   85.00  178.00   1.0000    6.0000
omega____ theta____ kappa____ phi______ frames
    -      110.2342   38.0000  -60.0000 93

140 omega   88.00  178.00   1.0000    6.0000
omega____ theta____ kappa____ phi______ frames
    -      110.2342   50.0000 -120.0000 90

141 omega   80.00  178.00   1.0000    6.0000
omega____ theta____ kappa____ phi______ frames
    -      110.2342   77.0000  120.0000 98

142 omega   88.00  178.00   1.0000    6.0000
omega____ theta____ kappa____ phi______ frames
    -      110.2342   50.0000   90.0000 90

143 omega   37.00  178.00   1.0000    6.0000
omega____ theta____ kappa____ phi______ frames
    -      110.2342  -12.0000  -30.0000 141

144 omega   85.00  178.00   1.0000    6.0000
omega____ theta____ kappa____ phi______ frames
    -      110.2342   38.0000    0.0000 93

145 omega   85.00  178.00   1.0000    6.0000
omega____ theta____ kappa____ phi______ frames
    -      110.2342   38.0000  150.0000 93

146 omega   40.00  140.00   1.0000    6.0000
omega____ theta____ kappa____ phi______ frames
    -      110.2342  -77.0000   90.0000 100

147 omega   88.00  178.00   1.0000    6.0000
omega____ theta____ kappa____ phi______ frames
    -      110.2342   50.0000  -90.0000 90

148 omega   37.00  178.00   1.0000    6.0000
omega____ theta____ kappa____ phi______ frames
    -      110.2342    0.0000    0.0000 141

149 omega   37.00  178.00   1.0000    6.0000
omega____ theta____ kappa____ phi______ frames
    -      110.2342    0.0000  120.0000 141

150 omega   37.00  178.00   1.0000    6.0000
omega____ theta____ kappa____ phi______ frames
    -      110.2342  -12.0000 -150.0000 141

151 omega   37.00  178.00   1.0000    6.0000
omega____ theta____ kappa____ phi______ frames
    -      110.2342    0.0000    0.0000 141

152 omega   37.00  178.00   1.0000    6.0000
omega____ theta____ kappa____ phi______ frames
    -      110.2342    0.0000  120.0000 141

153 omega   37.00  178.00   1.0000    6.0000
omega____ theta____ kappa____ phi______ frames
    -      110.2342    0.0000  240.0000 141

154 omega   88.00  178.00   1.0000    6.0000
omega____ theta____ kappa____ phi______ frames
    -      110.2342   50.0000   30.0000 90

155 omega   37.00  178.00   1.0000    6.0000
omega____ theta____ kappa____ phi______ frames
    -      110.2342  -12.0000 -180.0000 141

156 omega   37.00  178.00   1.0000    6.0000
omega____ theta____ kappa____ phi______ frames
    -      110.2342    0.0000  240.0000 141

157 omega   38.00   93.00   1.0000    6.0000
omega____ theta____ kappa____ phi______ frames
    -      110.2342  -38.0000  -90.0000 55

158 omega   37.00  178.00   1.0000    6.0000
omega____ theta____ kappa____ phi______ frames
    -      110.2342    0.0000  120.0000 141

159 omega   37.00  178.00   1.0000    6.0000
omega____ theta____ kappa____ phi______ frames
    -      110.2342  -12.0000 -120.0000 141

160 omega   37.00  178.00   1.0000    6.0000
omega____ theta____ kappa____ phi______ frames
    -      110.2342  -12.0000  -90.0000 141

161 omega   37.00  178.00   1.0000    6.0000
omega____ theta____ kappa____ phi______ frames
    -      110.2342  -12.0000  -60.0000 141

162 omega   37.00  178.00   1.0000    6.0000
omega____ theta____ kappa____ phi______ frames
    -      110.2342    0.0000    0.0000 141

163 omega   90.00  178.00   1.0000    6.0000
omega____ theta____ kappa____ phi______ frames
    -      110.2342   54.0000 -167.0000 88

164 omega  -73.00   43.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -        0.0000    0.0000  120.0000 116

165 omega  -73.00   73.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -        0.0000    0.0000    0.0000 146

;
_diffrn_measurement_device       '\k-geometry diffractometer'
_diffrn_measurement_device_type  'Agilent SuperNova, Dual, Cu at zero, Eos'
_diffrn_measurement_method       '\w scans'
_diffrn_measurement_specimen_support 'polyimid foil'
_diffrn_orient_matrix_UB_11      -0.0869636000
_diffrn_orient_matrix_UB_12      -0.0812117000
_diffrn_orient_matrix_UB_13      -0.0471840000
_diffrn_orient_matrix_UB_21      0.0326431000
_diffrn_orient_matrix_UB_22      -0.1306601000
_diffrn_orient_matrix_UB_23      0.0808458000
_diffrn_orient_matrix_UB_31      -0.1564041000
_diffrn_orient_matrix_UB_32      0.0627400000
_diffrn_orient_matrix_UB_33      0.1073404000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.5418
_diffrn_reflns_av_R_equivalents  0.0630
_diffrn_reflns_av_sigmaI/netI    0.0882
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            49191
_diffrn_reflns_theta_full        66.97
_diffrn_reflns_theta_max         71.7527
_diffrn_reflns_theta_min         4.0836
_diffrn_source                   'Agilent SuperNova (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    0.886
_exptl_absorpt_correction_T_max  0.964
_exptl_absorpt_correction_T_min  0.922
_exptl_absorpt_correction_type   analytical
_exptl_absorpt_process_details
;
CrysAlisPro, Agilent Technologies,
Version 1.171.35.21 (release 20-01-2012 CrysAlis171 .NET)
(compiled Jan 23 2012,18:06:46)
Analytical numeric absorption correction using a multifaceted crystal
            model based on expressions derived by R.C. Clark & J.S. Reid.
(Clark, R. C. & Reid, J. S. (1995). Acta Cryst. A51, 887-897)
;
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.292
_exptl_crystal_description       irregular
_exptl_crystal_F_000             392
_exptl_crystal_size_max          0.2811
_exptl_crystal_size_mid          0.1707
_exptl_crystal_size_min          0.1022
_refine_diff_density_max         0.379
_refine_diff_density_min         -0.294
_refine_diff_density_rms         0.050
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.035
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     275
_refine_ls_number_reflns         3658
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.035
_refine_ls_R_factor_all          0.0417
_refine_ls_R_factor_gt           0.0409
_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^)+(0.0645P)^2^+0.3777P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1101
_refine_ls_wR_factor_ref         0.1111
_reflns_number_gt                3548
_reflns_number_total             3658
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ja3039773_si_002_2.cif
_cod_data_source_block           ga_qd11
_cod_original_cell_volume        952.20(3)
_cod_database_code               4118185
_audit_block_refno               1479
_audit_block_usercomment         'd6-140, irregular, colourless'
_cell_oxdiff_length_a            9.49361(19)
_cell_oxdiff_length_b            9.58112(19)
_cell_oxdiff_length_c            11.7944(2)
_cell_oxdiff_angle_alpha         84.2465(16)
_cell_oxdiff_angle_beta          66.5081(18)
_cell_oxdiff_angle_gamma         75.4175(17)
_cell_oxdiff_volume              952.20(3)
_cell_oxdiff_measurement_reflns_used 32660
_reflns_odcompleteness_completeness 98.44
_reflns_odcompleteness_theta     66.97
_reflns_odcompleteness_iscentric 1