Enantioselective Synthesis of Trisubstituted Allenes via Cu(I)-Catalyzed Coupling of Diazoalkanes with Terminal Alkynes.
Chu, Wen-Dao; Zhang, Lei; Zhang, Zhikun; Zhou, Qi; Mo, Fanyang; Zhang, Yan; Wang, Jianbo; Journal of the American Chemical Society 138 (2016) 14558–14561; doi:10.1021/jacs.6b09674

data_4131125
_publ_section_title
;
 Enantioselective Synthesis of Trisubstituted Allenes via Cu(I)-Catalyzed
 Coupling of Diazoalkanes with Terminal Alkynes.
;
_journal_issue                   44
_journal_name_full               'Journal of the American Chemical Society'
_journal_page_first              14558
_journal_page_last               14561
_journal_paper_doi               10.1021/jacs.6b09674
_journal_volume                  138
_journal_year                    2016
_chemical_formula_moiety         'C22 H18'
_chemical_formula_sum            'C22 H18'
_chemical_formula_weight         282.36
_space_group_crystal_system      monoclinic
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_space_group_name_Hall           'P 2yb'
_space_group_name_H-M_alt        'P 1 21 1'
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Olex2 1.2
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CrysAlisPro, Agilent Technologies,
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CrysAlisPro, Agilent Technologies,
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omega____ theta____ kappa____ phi______ frames
    -       52.0000   80.0000   32.8574 28

138 omega   22.00   49.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -       56.0000   78.0000    4.8914 27

139 omega   22.00   49.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -       56.0000   78.0000  -63.8824 27

140 omega   23.00  134.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -       56.0000   76.0000   54.1928 111

141 omega   26.00  139.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -       60.0000   77.0000  146.6495 113

142 omega   27.00  137.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -       60.0000   74.0000 -145.5454 110

143 omega   31.00  142.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -       64.0000   76.0000  -29.2156 111

144 omega   31.00  142.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -       64.0000   76.0000   47.6154 111

145 omega   34.00  147.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -       68.0000   77.0000  -89.2719 113

146 omega   35.00  146.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -       68.0000   76.0000  153.5208 111

147 omega   35.00  146.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -       68.0000   75.0000 -125.1544 111

148 omega   38.00  151.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -       72.0000   77.0000   94.9029 113

149 omega   39.00  149.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -       72.0000   73.0000  -39.0107 110

150 omega   48.00  156.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -       80.0000   71.0000  137.4964 108

151 omega   49.00  154.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -       80.0000   62.0000 -161.2363 105

152 omega   52.00  160.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -       84.0000   69.0000   33.4499 108

153 omega   60.00  167.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -       92.0000   68.0000   91.7367 107

154 omega   64.00  172.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -       96.0000   71.0000  173.0942 108

155 omega   69.00  171.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -       96.0000   40.0000  -91.0506 102

156 omega   63.00  173.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -       96.0000   73.0000  116.4997 110

157 omega   68.00  176.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      100.0000   70.0000  -15.4257 108

158 omega   67.00  177.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      100.0000   72.0000   91.5391 110

159 omega   79.00  178.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000   77.0000 -150.0000 99

160 omega   37.00  120.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000 -121.0000 -123.3961 83

161 omega   79.00  178.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000   77.0000   30.0000 99

162 omega   79.00  178.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000   77.0000  -60.0000 99

163 omega   83.00  178.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000   61.0000  -90.0000 95

164 omega   24.00  178.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000    0.0000 -120.0000 154

165 omega   24.00  178.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000    0.0000 -150.0000 154

166 omega   24.00  178.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000    0.0000 -180.0000 154

167 omega   85.00  178.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000   45.0000  -60.0000 93

168 omega   24.00  178.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000    0.0000  -90.0000 154

169 omega   85.00  178.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000   45.0000  -90.0000 93
;
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, Atlas'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_UB_11      -0.1802443000
_diffrn_orient_matrix_UB_12      -0.0908161000
_diffrn_orient_matrix_UB_13      -0.0222444000
_diffrn_orient_matrix_UB_21      0.0630780000
_diffrn_orient_matrix_UB_22      -0.2576611000
_diffrn_orient_matrix_UB_23      -0.0054063000
_diffrn_orient_matrix_UB_31      0.0033344000
_diffrn_orient_matrix_UB_32      -0.0388709000
_diffrn_orient_matrix_UB_33      0.0878925000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.2039
_diffrn_reflns_av_unetI/netI     0.0493
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       6
_diffrn_reflns_limit_k_min       -6
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            60024
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         72.032
_diffrn_reflns_theta_min         5.215
_diffrn_source                   'SuperNova (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    0.507
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.35742
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.32 (release 02-08-2013 CrysAlis171 .NET)
(compiled Aug  2 2013,16:46:58)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour
;
;
_exptl_crystal_density_diffrn    1.195
_exptl_crystal_description
;
;
_exptl_crystal_F_000             300
_exptl_crystal_size_max          0.1
_exptl_crystal_size_mid          0.1
_exptl_crystal_size_min          0.05
_refine_diff_density_max         0.242
_refine_diff_density_min         -0.197
_refine_diff_density_rms         0.045
_refine_ls_abs_structure_details
;
 Flack x determined using 1340 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.1(7)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.041
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     200
_refine_ls_number_reflns         3076
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.041
_refine_ls_R_factor_all          0.0431
_refine_ls_R_factor_gt           0.0429
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0674P)^2^+0.1086P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1175
_refine_ls_wR_factor_ref         0.1178
_reflns_Friedel_coverage         0.800
_reflns_Friedel_fraction_full    0.998
_reflns_Friedel_fraction_max     0.995
_reflns_number_gt                3048
_reflns_number_total             3076
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            ja6b09674_si_002.cif
_cod_data_source_block           exp_7705
_cod_original_cell_volume        784.549(16)
_cod_database_code               4131125
_shelxl_version_number           2014-3
_chemical_oxdiff_formula         'C22 H18'
_shelx_estimated_absorpt_t_max   0.975
_shelx_estimated_absorpt_t_min   0.951
_reflns_odcompleteness_completeness 99.88
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     71.98
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C2(H2), C3(H3), C5(H5), C6(H6), C8(H8), C9(H9), C10(H10), C11(H11), C12(H12),
 C15(H15), C18(H18), C19(H19), C20(H20), C21(H21), C22(H22)
2.b Idealised Me refined as rotating group:
 C16(H16A,H16B,H16C)
;
_olex2_submission_special_instructions 'No special instructions were received'