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_4514681
_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         'C11 H10 I0.96 N O'
_chemical_formula_sum            'C11 H10 I0.96 N O'
_chemical_formula_weight         294.02
_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             2019-04-02
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_cell_angle_alpha                90
_cell_angle_beta                 99.353(5)
_cell_angle_gamma                90
_cell_formula_units_Z            2
_cell_length_a                   9.8268(5)
_cell_length_b                   5.6439(3)
_cell_length_c                   9.8652(5)
_cell_measurement_reflns_used    1478
_cell_measurement_temperature    99.95(17)
_cell_measurement_theta_max      29.8390
_cell_measurement_theta_min      11.1400
_cell_volume                     539.86(5)
_computing_cell_refinement       'CrysAlisPro 1.171.40.42a (Rigaku OD, 2019)'
_computing_data_collection       'CrysAlisPro 1.171.40.42a (Rigaku OD, 2019)'
_computing_data_reduction        'CrysAlisPro 1.171.40.42a (Rigaku OD, 2019)'
_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      99.95(17)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.879
_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    -93.00 -11.00   1.00    1.00    --   -5.00  23.00  92.00   82
  2  \w    -37.00  30.00   1.00    1.00    --    7.50  23.00  92.00   67
  3  \w     46.00  95.00   1.00    1.00    --    7.50  60.00  30.00   49
  4  \w     48.00  75.00   1.00    1.00    --    7.50  30.00 -30.00   27
  5  \w    -53.00  96.00   1.00    1.00    --    7.50  50.00   0.00  149
  6  \w    -78.00  23.00   1.00    1.00    --    7.50  60.00-150.00  101
  7  \w    -38.00   6.00   1.00    1.00    --    7.50  60.00  30.00   44
;
_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      -0.0259207000
_diffrn_orient_matrix_UB_12      -0.0491893000
_diffrn_orient_matrix_UB_13      -0.0652702000
_diffrn_orient_matrix_UB_21      -0.0672637000
_diffrn_orient_matrix_UB_22      -0.0026364000
_diffrn_orient_matrix_UB_23      0.0173093000
_diffrn_orient_matrix_UB_31      -0.0124807000
_diffrn_orient_matrix_UB_32      0.1156624000
_diffrn_orient_matrix_UB_33      -0.0273324000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0447
_diffrn_reflns_av_unetI/netI     0.0525
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.879
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_number            3833
_diffrn_reflns_point_group_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.826
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         30.218
_diffrn_reflns_theta_min         2.092
_diffrn_source                   'Rotating-anode X-ray tube (dual wavelength)'
_diffrn_source_type              'Rigaku (Mo) X-ray DW Source'
_exptl_absorpt_coefficient_mu    2.818
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.64767
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.40.42a (Rigaku Oxford Diffraction, 2019)
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    1.809
_exptl_crystal_description       needle
_exptl_crystal_F_000             284
_exptl_crystal_size_max          0.249
_exptl_crystal_size_mid          0.017
_exptl_crystal_size_min          0.015
_refine_diff_density_max         2.561
_refine_diff_density_min         -2.481
_refine_diff_density_rms         0.307
_refine_ls_abs_structure_details
;
 Flack x determined using 940 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.02(7)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.228
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     130
_refine_ls_number_reflns         3833
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.228
_refine_ls_R_factor_all          0.0714
_refine_ls_R_factor_gt           0.0590
_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^)+(0.1049P)^2^+11.8661P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2182
_refine_ls_wR_factor_ref         0.2365
_reflns_Friedel_coverage         0.720
_reflns_Friedel_fraction_full    0.994
_reflns_Friedel_fraction_max     0.763
_reflns_number_gt                3332
_reflns_number_total             3833
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            cs9b01911_si_004.cif
_cod_data_source_block           s5447l_twin1_hklf4
_cod_database_code               4514681
_shelx_shelxl_version_number     2018/1
_shelx_estimated_absorpt_t_max   0.959
_shelx_estimated_absorpt_t_min   0.541
_olex2_refinement_description
;
1. Twinned data refinement
 Scales: 0.496(11)
 0.271(8) 0.233(7)
2. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
3.a Ternary CH refined with riding coordinates:
 C4(H4), C1(H1), C2(H2)
3.b Secondary CH2 refined with riding coordinates:
 C3(H3A,H3B)
3.c Aromatic/amide H refined with riding coordinates:
 C8(H8), C9(H9), C10(H10), C6(H6), C7(H7)
;
_shelx_res_checksum              38699
_shelx_hkl_checksum              46425
_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 1.370
_oxdiff_exptl_absorpt_empirical_full_min 0.683
_oxdiff_twin_integration_method  simultaneous
_oxdiff_twin_items               3
_twin_special_details
;
Component 2 rotated by 1.1210\% 
 around [0.21 -0.98 0.03] (reciprocal) or [0.08 -1.00 0.02] (direct)
Component 3 rotated by 1.6544\% 
 around [-0.12 0.01 0.99] (reciprocal) or [0.05 0.04 1.00] (direct)
;