Enantioselective Copper-Catalyzed Oxy-Alkynylation of Diazo Compounds.
Hari, Durga Prasad; Waser, Jerome; Journal of the American Chemical Society 139 (2017) 8420–8423; doi:10.1021/jacs.7b04756

data_4131348
_publ_section_title
;
 Enantioselective Copper-Catalyzed Oxy-Alkynylation of Diazo Compounds.
;
_journal_issue                   25
_journal_name_full               'Journal of the American Chemical Society'
_journal_page_first              8420
_journal_page_last               8423
_journal_paper_doi               10.1021/jacs.7b04756
_journal_volume                  139
_journal_year                    2017
_chemical_absolute_configuration rmad
_chemical_formula_sum            'C36 H51 I O4 Si'
_chemical_formula_weight         702.76
_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   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-2016/6
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   9.3812(2)
_cell_length_b                   12.8730(2)
_cell_length_c                   29.8093(7)
_cell_measurement_reflns_used    18603
_cell_measurement_temperature    140.00(10)
_cell_measurement_theta_max      73.3620
_cell_measurement_theta_min      3.7060
_cell_volume                     3599.90(13)
_computing_cell_refinement       'CrysAlisPro 1.171.38.43 (Rigaku OD, 2015)'
_computing_data_collection       'CrysAlisPro 1.171.38.43 (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.38.43 (Rigaku OD, 2015)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'CIFTAB (Sheldrick, 2016)'
_computing_structure_refinement  'SHELXL-2016/6 (Sheldrick, 2016)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      140.00(10)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 5.1333
_diffrn_detector_type            Atlas
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.990
_diffrn_measurement_details
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  t~exp~   \w     \q     \k     \f   Frames
--------------------------------------------------------------------------
  1  \w    -70.00  20.00   1.00    1.00    --  -42.26  57.00 -30.00   90
  2  \w    -28.00  -2.00   1.00    1.00    --  -42.26 125.00-120.00   26
  3  \w    -65.00  24.00   1.00    1.00    --  -42.26  57.00-180.00   89
  4  \w    -89.00 -64.00   1.00    1.00    --  -42.26 125.00-120.00   25
  5  \w   -115.00 -15.00   1.00    1.00    --  -42.26 -57.00  30.00  100
  6  \w   -104.00 -76.00   1.00    1.00    --  -42.26-147.00  95.00   28
  7  \w     33.00  94.00   1.00    2.48    --  105.68 -45.00  60.00   61
  8  \w     54.00  89.00   1.00    2.48    --  105.68 -77.00 150.00   35
  9  \w     23.00 107.00   1.00    2.48    --  105.68 -94.00  90.00   84
 10  \w     54.00 106.00   1.00    2.48    --  105.68 -94.00   0.00   52
 11  \w     94.00 122.00   1.00    2.48    --  105.68-125.00 -60.00   28
 12  \w     71.00 130.00   1.00    2.48    --  105.68 -45.00-120.00   59
 13  \w    111.00 178.00   1.00    2.48    --  105.68  77.00 -60.00   67
 14  \w    118.00 145.00   1.00    2.48    --  105.68 125.00 -30.00   27
 15  \w    110.00 173.00   1.00    2.48    --  105.68 125.00  60.00   63
 16  \w     34.00  71.00   1.00    2.48    --  105.68 -61.00   0.00   37
 17  \w     35.00  73.00   1.00    2.48    --  105.68-125.00 -60.00   38
 18  \w     24.00  89.00   1.00    2.48    --  105.68 -94.00-120.00   65
 19  \w     19.00 175.00   1.00    2.48    --  105.68   0.00 -60.00  156
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, Atlas'
_diffrn_measurement_method       '\w scans'
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0451
_diffrn_reflns_av_unetI/netI     0.0352
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.990
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       37
_diffrn_reflns_limit_l_min       -36
_diffrn_reflns_number            25820
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.982
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         73.880
_diffrn_reflns_theta_min         3.740
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    7.573
_exptl_absorpt_correction_T_max  0.14825
_exptl_absorpt_correction_T_min  0.05124
_exptl_absorpt_correction_type   sphere
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.38.43 (Rigaku Oxford Diffraction, 2015)
Spherical absorption correction using equivalent radius
and absorption coefficient.
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.297
_exptl_crystal_description       prism
_exptl_crystal_F_000             1464
_exptl_crystal_size_max          0.486
_exptl_crystal_size_mid          0.253
_exptl_crystal_size_min          0.180
_exptl_crystal_size_rad          0.1532
_refine_diff_density_max         2.291
_refine_diff_density_min         -0.622
_refine_diff_density_rms         0.086
_refine_ls_abs_structure_details
;
 Flack x determined using 2890 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.003(5)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.073
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     444
_refine_ls_number_reflns         7160
_refine_ls_number_restraints     111
_refine_ls_restrained_S_all      1.070
_refine_ls_R_factor_all          0.0494
_refine_ls_R_factor_gt           0.0491
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0882P)^2^+2.0106P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1364
_refine_ls_wR_factor_ref         0.1368
_reflns_Friedel_coverage         0.761
_reflns_Friedel_fraction_full    1.000
_reflns_Friedel_fraction_max     0.972
_reflns_number_gt                7073
_reflns_number_total             7160
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            ja7b04756_si_002.cif
_cod_data_source_block           shelx
_cod_database_code               4131348
_shelx_shelxl_version_number     2016/6
_shelx_res_checksum              94225
_shelx_hkl_checksum              11480