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_4514679
_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         'C17 H21 B Br N O2'
_chemical_formula_sum            'C17 H21 B Br N O2'
_chemical_formula_weight         362.07
_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             2019-01-24
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_cell_angle_alpha                90
_cell_angle_beta                 91.376(3)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   11.3502(4)
_cell_length_b                   7.4500(2)
_cell_length_c                   20.6376(6)
_cell_measurement_reflns_used    12081
_cell_measurement_temperature    100.03(15)
_cell_measurement_theta_max      28.4390
_cell_measurement_theta_min      1.7870
_cell_volume                     1744.59(9)
_computing_cell_refinement       'CrysAlisPro 1.171.40.35a (Rigaku OD, 2018)'
_computing_data_collection       'CrysAlisPro 1.171.40.35a (Rigaku OD, 2018)'
_computing_data_reduction        'CrysAlisPro 1.171.40.35a (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      100.03(15)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.877
_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    -24.00  52.00   1.00    2.00    --    7.50  22.00-109.00   76
  2  \w    -81.00  95.00   1.00    2.00    --    7.50  40.00 120.00  176
  3  \w    -79.00  94.00   1.00    2.00    --    7.50  60.00-180.00  173
  4  \w    -76.00 -48.00   1.00    2.00    --    7.50  10.00   0.00   28
  5  \w     25.00  50.00   1.00    2.00    --    7.50  10.00   0.00   25
  6  \w     58.00  96.00   1.00    2.00    --    7.50  60.00 150.00   38
  7  \w    -33.00  -8.00   1.00    2.00    --    7.50  10.00  30.00   25
  8  \w     58.00  83.00   1.00    2.00    --    7.50  22.00-109.00   25
;
_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      -0.0424750000
_diffrn_orient_matrix_UB_12      0.0340363000
_diffrn_orient_matrix_UB_13      0.0214863000
_diffrn_orient_matrix_UB_21      0.0403684000
_diffrn_orient_matrix_UB_22      -0.0115671000
_diffrn_orient_matrix_UB_23      0.0264237000
_diffrn_orient_matrix_UB_31      0.0217562000
_diffrn_orient_matrix_UB_32      0.0881594000
_diffrn_orient_matrix_UB_33      -0.0047163000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0547
_diffrn_reflns_av_unetI/netI     0.0597
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.877
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       27
_diffrn_reflns_limit_l_min       -29
_diffrn_reflns_number            29396
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.826
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         30.409
_diffrn_reflns_theta_min         1.795
_diffrn_source                   'Rotating-anode X-ray tube (dual wavelength)'
_diffrn_source_type              'Rigaku (Mo) X-ray DW Source'
_exptl_absorpt_coefficient_mu    2.362
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.38068
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.40.35a (Rigaku Oxford Diffraction, 2018)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            'clear colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.378
_exptl_crystal_description       block
_exptl_crystal_F_000             744
_exptl_crystal_size_max          0.452
_exptl_crystal_size_mid          0.266
_exptl_crystal_size_min          0.07
_refine_diff_density_max         0.790
_refine_diff_density_min         -0.448
_refine_diff_density_rms         0.067
_refine_ls_abs_structure_details
;
 Flack x determined using 2816 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.002(6)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.051
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     405
_refine_ls_number_reflns         8734
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.051
_refine_ls_R_factor_all          0.0536
_refine_ls_R_factor_gt           0.0407
_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^)+(0.0315P)^2^+0.8322P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0861
_refine_ls_wR_factor_ref         0.0894
_reflns_Friedel_coverage         0.759
_reflns_Friedel_fraction_full    1.000
_reflns_Friedel_fraction_max     0.767
_reflns_number_gt                7380
_reflns_number_total             8734
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            cs9b01911_si_002.cif
_cod_data_source_block           s5394l
_cod_database_code               4514679
_shelx_shelxl_version_number     2018/1
_shelx_estimated_absorpt_t_max   0.852
_shelx_estimated_absorpt_t_min   0.415
_diffrn_oxdiff_digest_frames
;
016b6daed9cced4fa0bdaa9ca578c662cc000287db9
;
_diffrn_oxdiff_digest_hkl
;
01ea8b2b7b16a0b82243deaa5db1e43d192bdc
;
_reflns_odcompleteness_completeness 99.95
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     26.32
_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:
 C9(H9), C26(H26)
2.b Secondary CH2 refined with riding coordinates:
 C11(H11A,H11B), C28(H28A,H28B)
2.c Aromatic/amide H refined with riding coordinates:
 C2(H2), C3(H3), C5(H5), C6(H6), C7(H7), C8(H8), C19(H19), C20(H20), C22(H22),
 C23(H23), C24(H24), C25(H25)
2.d Idealised Me refined as rotating group:
 C14(H14A,H14B,H14C), C15(H15A,H15B,H15C), C16(H16A,H16B,H16C), C17(H17A,H17B,
 H17C), C31(H31A,H31B,H31C), C32(H32A,H32B,H32C), C33(H33A,H33B,H33C), C34(H34A,
 H34B,H34C)
;
_shelx_res_checksum              69818
_shelx_hkl_checksum              51646
_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 1.629
_oxdiff_exptl_absorpt_empirical_full_min 0.645