Enantioselective and Regioselective Copper-Catalyzed Borocyanation of 1-Aryl-1,3-Butadienes
Jia, Tao; Smith, Marshall J.; Pulis, Alexander P.; Perry, Gregory J. P.; Procter, David J.; ACS Catalysis 9 (2019) 6744–; doi:10.1021/acscatal.9b01911

data_4514680
_publ_section_title
;
 Enantioselective and Regioselective Copper-Catalyzed Borocyanation of
 1-Aryl-1,3-Butadienes
;
_journal_issue                   8
_journal_name_full               'ACS Catalysis'
_journal_page_first              6744
_journal_paper_doi               10.1021/acscatal.9b01911
_journal_volume                  9
_journal_year                    2019
_chemical_absolute_configuration ad
_chemical_formula_moiety         'C20 H16 Br N O2'
_chemical_formula_sum            'C20 H16 Br N O2'
_chemical_formula_weight         382.25
_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'
_symmetry_space_group_name_Hall  'P 2yb'
_symmetry_space_group_name_H-M   'P 1 21 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_audit_creation_date             2019-03-22
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_cell_angle_alpha                90
_cell_angle_beta                 97.0979(12)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   14.62776(18)
_cell_length_b                   8.05742(10)
_cell_length_c                   15.00218(18)
_cell_measurement_reflns_used    17466
_cell_measurement_temperature    100.0(3)
_cell_measurement_theta_max      75.6730
_cell_measurement_theta_min      2.9550
_cell_volume                     1754.64(4)
_computing_cell_refinement       'CrysAlisPro 1.171.40.14d (Rigaku OD, 2018)'
_computing_data_collection       'CrysAlisPro 1.171.40.14d (Rigaku OD, 2018)'
_computing_data_reduction        'CrysAlisPro 1.171.40.14d (Rigaku OD, 2018)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      100.0(3)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_measured_fraction_theta_full 0.903
_diffrn_measured_fraction_theta_max 0.957
_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     84.00 134.00   1.00    1.00    --   44.80  40.00-180.00   50
  2  \w     27.00  88.00   1.00    1.00    --   44.80  50.00 120.00   61
  3  \w     -8.00 133.00   1.00    1.00    --   44.80  30.00   0.00  141
  4  \w    -29.00  -3.00   1.00    1.00    --   44.80  50.00 120.00   26
  5  \w     29.00  56.00   1.00    1.00    --   44.80  40.00-180.00   27
  6  \w    -45.00 134.00   1.00    1.00    --   44.80  60.00 -30.00  179
  7  \w     88.00 115.00   1.00    1.00    --   44.80   0.00-180.00   27
  8  \w     90.00 123.00   1.00    1.00    --   44.80  50.00 120.00   33
  9  \w     20.00 198.00   1.00    1.00    --  108.20  50.00-180.00  178
 10  \w    150.00 176.00   1.00    1.00    --  108.20  50.00  60.00   26
 11  \w    121.00 196.00   1.00    1.00    --  108.20  50.00   0.00   75
 12  \w    148.00 175.00   1.00    1.00    --  108.20  50.00 -90.00   27
 13  \w     77.00 132.00   1.00    1.00    --  108.20  50.00  60.00   55
 14  \w     58.00  85.00   1.00    1.00    --  108.20  50.00 120.00   27
 15  \w    145.00 188.00   1.00    1.00    --  108.20  50.00-150.00   43
 16  \w     51.00 111.00   1.00    1.00    --  108.20  50.00   0.00   60
 17  \w     75.00 101.00   1.00    1.00    --  108.20  50.00-150.00   26
 18  \w     20.00 197.00   1.00    1.00    --  108.20  50.00  30.00  177
 19  \w    112.00 178.00   1.00    1.00    --  108.20  50.00 -60.00   66
 20  \w    145.00 198.00   1.00    1.00    --  108.20  50.00 120.00   53
 21  \w     45.00 168.00   1.00    1.00    --  108.20  50.00 150.00  123
 22  \w    127.00 152.00   1.00    1.00    --  108.20  30.00  90.00   25
 23  \w     28.00 195.00   1.00    1.00    --  108.20  40.00-120.00  167
 24  \w    142.00 170.00   1.00    1.00    --  108.20  50.00  90.00   28
 25  \w     19.00 116.00   1.00    1.00    --  108.20  30.00  90.00   97
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB AFC11 (RINC): quarter-chi single'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0824455000
_diffrn_orient_matrix_UB_12      -0.0350766000
_diffrn_orient_matrix_UB_13      -0.0717713000
_diffrn_orient_matrix_UB_21      0.0253761000
_diffrn_orient_matrix_UB_22      -0.1857836000
_diffrn_orient_matrix_UB_23      0.0018031000
_diffrn_orient_matrix_UB_31      -0.0617087000
_diffrn_orient_matrix_UB_32      -0.0293960000
_diffrn_orient_matrix_UB_33      0.0745277000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0396
_diffrn_reflns_av_unetI/netI     0.0296
_diffrn_reflns_Laue_measured_fraction_full 0.903
_diffrn_reflns_Laue_measured_fraction_max 0.957
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_h_min       -17
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            16624
_diffrn_reflns_point_group_measured_fraction_full 0.893
_diffrn_reflns_point_group_measured_fraction_max 0.948
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         65.082
_diffrn_reflns_theta_min         2.968
_diffrn_source                   'Rotating-anode X-ray tube (dual wavelength)'
_diffrn_source_type              'Rigaku (Cu) X-ray DW Source'
_exptl_absorpt_coefficient_mu    3.280
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.63817
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.40.14d (Rigaku Oxford Diffraction, 2018)
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
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.447
_exptl_crystal_description       block
_exptl_crystal_F_000             776
_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.1
_refine_diff_density_max         0.293
_refine_diff_density_min         -0.380
_refine_diff_density_rms         0.051
_refine_ls_abs_structure_details
;
 Flack x determined using 2432 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.016(13)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.063
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     433
_refine_ls_number_reflns         5680
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.062
_refine_ls_R_factor_all          0.0359
_refine_ls_R_factor_gt           0.0322
_refine_ls_shift/su_max          0.003
_refine_ls_shift/su_mean         0.001
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0597P)^2^+0.7321P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0875
_refine_ls_wR_factor_ref         0.0942
_reflns_Friedel_coverage         0.836
_reflns_Friedel_fraction_full    0.881
_reflns_Friedel_fraction_max     0.938
_reflns_number_gt                5489
_reflns_number_total             5680
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            cs9b01911_si_003.cif
_cod_data_source_block           s5433l
_cod_database_code               4514680
_shelxl_version_number           2014/6
_shelx_estimated_absorpt_t_max   0.735
_shelx_estimated_absorpt_t_min   0.560
_diffrn_oxdiff_digest_frames
;
011050bce5ddea884c0675312cd00598ad00032ba15
;
_diffrn_oxdiff_digest_hkl
;
01c197746489d0ec663e9a4ea6f575fe144106
;
_reflns_odcompleteness_completeness 95.85
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     68.13
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
2.a Ternary CH refined with riding coordinates:
 C7(H7), C27(H27)
2.b Secondary CH2 refined with riding coordinates:
 C6(H6A,H6B), C26(H26A,H26B)
2.c Aromatic/amide H refined with riding coordinates:
 C10(H10), C12(H12), C17(H17), C15(H15), C14(H14), C13(H13), C16(H16), C3(H3),
 C19(H19), C2(H2), C20(H20), C35(H35), C32(H32), C30(H30), C37(H37), C22(H22),
 C40(H40), C36(H36), C23(H23), C34(H34), C33(H33), C39(H39)
2.d X=CH2 refined with riding coordinates:
 C18(H18A,H18B), C38(H38A,H38B)
;
_shelx_res_checksum              39202
_shelx_hkl_checksum              97684
_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 1.649
_oxdiff_exptl_absorpt_empirical_full_min 0.787