#------------------------------------------------------------------------------
#$Date: 2020-10-03 00:22:38 +0300 (Sat, 03 Oct 2020) $
#$Revision: 256945 $
#$URL: file:///home/coder/svn-repositories/cod/cif/4/51/81/4518108.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/
#
# All data on this site have been placed in the public domain by the
# contributors.
#
data_4518108
loop_
_publ_author_name
'Li, Zhenghua'
'Zhang, Liang'
'Nishiura, Masayoshi'
'Luo, Gen'
'Luo, Yi'
'Hou, Zhaomin'
_publ_section_title
;
 Enantioselective Cyanoborylation of Allenes by N-Heterocyclic
 Carbene-Copper Catalysts
;
_journal_name_full               'ACS Catalysis'
_journal_page_first              11685
_journal_page_last               11692
_journal_paper_doi               10.1021/acscatal.0c03018
_journal_year                    2020
_chemical_absolute_configuration ad
_chemical_formula_moiety         'C14 H18 Br N'
_chemical_formula_sum            'C14 H18 Br N'
_chemical_formula_weight         280.20
_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
_audit_creation_method           SHELXL-2018/3
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   6.4796(2)
_cell_length_b                   10.8112(4)
_cell_length_c                   17.4816(6)
_cell_measurement_reflns_used    240
_cell_measurement_temperature    173(2)
_cell_measurement_theta_max      25
_cell_measurement_theta_min      2
_cell_volume                     1224.63(7)
_computing_cell_refinement       'Bruker SMART APEX3 v2016.1-0'
_computing_data_collection       'Bruker SMART APEX3 v2016.1-0'
_computing_data_reduction        'Bruker SMART APEX3 v2016.1-0'
_computing_molecular_graphics    'Ortep-3 for Windows (Farrugia, 2012)'
_computing_publication_material  'WinGX publication routines (Farrugia, 2012)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_diffrn_ambient_temperature      173(2)
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measurement_device_type  'Bruker D8 Quest with CMOS'
_diffrn_measurement_method       'phi and omega scan'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0502
_diffrn_reflns_av_unetI/netI     0.0401
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_number            10435
_diffrn_reflns_point_group_measured_fraction_full 0.994
_diffrn_reflns_point_group_measured_fraction_max 0.994
_diffrn_reflns_theta_full        25.019
_diffrn_reflns_theta_max         25.019
_diffrn_reflns_theta_min         2.215
_exptl_absorpt_coefficient_mu    3.329
_exptl_absorpt_correction_T_max  0.745
_exptl_absorpt_correction_T_min  0.305
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   SADABS
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.520
_exptl_crystal_description       plate
_exptl_crystal_F_000             576
_exptl_crystal_size_max          0.480
_exptl_crystal_size_mid          0.450
_exptl_crystal_size_min          0.150
_refine_diff_density_max         0.329
_refine_diff_density_min         -0.449
_refine_diff_density_rms         0.069
_refine_ls_abs_structure_details
;
 Refined as an inversion twin.
;
_refine_ls_abs_structure_Flack   0.027(13)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.045
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     146
_refine_ls_number_reflns         2154
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.045
_refine_ls_R_factor_all          0.0258
_refine_ls_R_factor_gt           0.0235
_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/[σ²(Fo²)+(0.0254P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0557
_refine_ls_wR_factor_ref         0.0567
_reflns_Friedel_coverage         0.684
_reflns_Friedel_fraction_full    0.986
_reflns_Friedel_fraction_max     0.986
_reflns_number_gt                2055
_reflns_number_total             2154
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            cs0c03018_si_002.cif
_cod_data_source_block           shelx
_cod_database_code               4518108
_shelx_shelxl_version_number     2018/3
_shelx_space_group_comment
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_shelx_estimated_absorpt_t_min   0.298
_shelx_estimated_absorpt_t_max   0.635
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'x+1/2, -y+1/2, -z'
'-x, y+1/2, -z+1/2'
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Br1 Br 0.70239(6) 0.70400(3) 0.28258(2) 0.02501(12) Uani 1 1 d . . . . .
N1 N 0.9145(6) 0.3751(3) 0.29767(18) 0.0309(8) Uani 1 1 d . . . . .
C1 C 0.5803(5) 0.4717(3) 0.35739(19) 0.0169(7) Uani 1 1 d . . . . .
H1 H 0.471082 0.406829 0.352640 0.020 Uiso 1 1 calc R U . . .
C2 C 0.7678(6) 0.4180(3) 0.32275(19) 0.0203(8) Uani 1 1 d . . . . .
C3 C 0.5032(6) 0.5820(3) 0.3112(2) 0.0204(8) Uani 1 1 d . . . . .
C4 C 0.3106(6) 0.5957(4) 0.2895(2) 0.0302(8) Uani 1 1 d . . . . .
H4A H 0.210771 0.534934 0.302505 0.036 Uiso 1 1 calc R U . . .
H4B H 0.271165 0.666452 0.260756 0.036 Uiso 1 1 calc R U . . .
C5 C 0.6130(5) 0.4914(3) 0.44533(19) 0.0138(7) Uani 1 1 d . . . . .
C6 C 0.7940(6) 0.5796(3) 0.46341(18) 0.0156(7) Uani 1 1 d . . . . .
H6A H 0.922501 0.547402 0.440166 0.019 Uiso 1 1 calc R U . . .
H6B H 0.765779 0.662220 0.441338 0.019 Uiso 1 1 calc R U . . .
C7 C 0.4147(5) 0.5425(3) 0.48087(19) 0.0155(7) Uani 1 1 d . . . . .
H7A H 0.298385 0.485843 0.469861 0.019 Uiso 1 1 calc R U . . .
H7B H 0.382257 0.624087 0.458095 0.019 Uiso 1 1 calc R U . . .
C8 C 0.6586(5) 0.3637(3) 0.48144(19) 0.0173(8) Uani 1 1 d . . . . .
H8A H 0.543738 0.306190 0.470148 0.021 Uiso 1 1 calc R U . . .
H8B H 0.786345 0.329027 0.458943 0.021 Uiso 1 1 calc R U . . .
C9 C 0.6846(6) 0.3765(3) 0.56857(18) 0.0187(7) Uani 1 1 d . . . . .
H9 H 0.713398 0.293269 0.591188 0.022 Uiso 1 1 calc R U . . .
C10 C 0.8652(5) 0.4625(3) 0.5850(2) 0.0198(8) Uani 1 1 d . . . . .
H10A H 0.993059 0.428035 0.562521 0.024 Uiso 1 1 calc R U . . .
H10B H 0.885384 0.469981 0.640978 0.024 Uiso 1 1 calc R U . . .
C11 C 0.8211(5) 0.5906(3) 0.55053(18) 0.0169(7) Uani 1 1 d . . . . .
H11 H 0.938786 0.647481 0.562016 0.020 Uiso 1 1 calc R U . . .
C12 C 0.6220(5) 0.6431(3) 0.5854(2) 0.0187(7) Uani 1 1 d . . . . .
H12A H 0.638483 0.652117 0.641377 0.022 Uiso 1 1 calc R U . . .
H12B H 0.593589 0.725898 0.563536 0.022 Uiso 1 1 calc R U . . .
C13 C 0.4413(5) 0.5561(3) 0.5681(2) 0.0176(8) Uani 1 1 d . . . . .
H13 H 0.311877 0.590585 0.590840 0.021 Uiso 1 1 calc R U . . .
C14 C 0.4867(5) 0.4287(3) 0.6035(2) 0.0204(8) Uani 1 1 d . . . . .
H14A H 0.502916 0.436862 0.659573 0.024 Uiso 1 1 calc R U . . .
H14B H 0.370103 0.371839 0.593369 0.024 Uiso 1 1 calc R U . . .
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Br Br -0.2901 2.4595 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C2 C1 C3 111.1(3) . . ?
C2 C1 C5 110.2(3) . . ?
C3 C1 C5 117.2(3) . . ?
C2 C1 H1 105.8 . . ?
C3 C1 H1 105.8 . . ?
C5 C1 H1 105.8 . . ?
N1 C2 C1 178.3(4) . . ?
C4 C3 C1 123.6(4) . . ?
C4 C3 Br1 119.2(3) . . ?
C1 C3 Br1 117.2(3) . . ?
C3 C4 H4A 120.0 . . ?
C3 C4 H4B 120.0 . . ?
H4A C4 H4B 120.0 . . ?
C7 C5 C6 109.3(3) . . ?
C7 C5 C8 108.5(3) . . ?
C6 C5 C8 108.8(3) . . ?
C7 C5 C1 109.5(3) . . ?
C6 C5 C1 112.8(3) . . ?
C8 C5 C1 107.8(3) . . ?
C11 C6 C5 109.7(3) . . ?
C11 C6 H6A 109.7 . . ?
C5 C6 H6A 109.7 . . ?
C11 C6 H6B 109.7 . . ?
C5 C6 H6B 109.7 . . ?
H6A C6 H6B 108.2 . . ?
C5 C7 C13 110.0(3) . . ?
C5 C7 H7A 109.7 . . ?
C13 C7 H7A 109.7 . . ?
C5 C7 H7B 109.7 . . ?
C13 C7 H7B 109.7 . . ?
H7A C7 H7B 108.2 . . ?
C9 C8 C5 110.2(3) . . ?
C9 C8 H8A 109.6 . . ?
C5 C8 H8A 109.6 . . ?
C9 C8 H8B 109.6 . . ?
C5 C8 H8B 109.6 . . ?
H8A C8 H8B 108.1 . . ?
C10 C9 C14 110.1(3) . . ?
C10 C9 C8 109.0(3) . . ?
C14 C9 C8 109.7(3) . . ?
C10 C9 H9 109.3 . . ?
C14 C9 H9 109.3 . . ?
C8 C9 H9 109.3 . . ?
C9 C10 C11 109.5(3) . . ?
C9 C10 H10A 109.8 . . ?
C11 C10 H10A 109.8 . . ?
C9 C10 H10B 109.8 . . ?
C11 C10 H10B 109.8 . . ?
H10A C10 H10B 108.2 . . ?
C12 C11 C6 109.0(3) . . ?
C12 C11 C10 109.5(3) . . ?
C6 C11 C10 109.9(3) . . ?
C12 C11 H11 109.5 . . ?
C6 C11 H11 109.5 . . ?
C10 C11 H11 109.5 . . ?
C13 C12 C11 109.7(3) . . ?
C13 C12 H12A 109.7 . . ?
C11 C12 H12A 109.7 . . ?
C13 C12 H12B 109.7 . . ?
C11 C12 H12B 109.7 . . ?
H12A C12 H12B 108.2 . . ?
C12 C13 C14 109.0(3) . . ?
C12 C13 C7 109.8(3) . . ?
C14 C13 C7 109.5(3) . . ?
C12 C13 H13 109.5 . . ?
C14 C13 H13 109.5 . . ?
C7 C13 H13 109.5 . . ?
C9 C14 C13 109.3(3) . . ?
C9 C14 H14A 109.8 . . ?
C13 C14 H14A 109.8 . . ?
C9 C14 H14B 109.8 . . ?
C13 C14 H14B 109.8 . . ?
H14A C14 H14B 108.3 . . ?
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Br1 C3 1.912(4) . ?
N1 C2 1.145(5) . ?
C1 C2 1.476(5) . ?
C1 C3 1.524(5) . ?
C1 C5 1.566(5) . ?
C1 H1 1.0000 . ?
C3 C4 1.313(5) . ?
C4 H4A 0.9500 . ?
C4 H4B 0.9500 . ?
C5 C7 1.531(5) . ?
C5 C6 1.544(5) . ?
C5 C8 1.546(4) . ?
C6 C11 1.538(4) . ?
C6 H6A 0.9900 . ?
C6 H6B 0.9900 . ?
C7 C13 1.542(5) . ?
C7 H7A 0.9900 . ?
C7 H7B 0.9900 . ?
C8 C9 1.539(4) . ?
C8 H8A 0.9900 . ?
C8 H8B 0.9900 . ?
C9 C10 1.522(5) . ?
C9 C14 1.529(5) . ?
C9 H9 1.0000 . ?
C10 C11 1.537(4) . ?
C10 H10A 0.9900 . ?
C10 H10B 0.9900 . ?
C11 C12 1.536(5) . ?
C11 H11 1.0000 . ?
C12 C13 1.531(5) . ?
C12 H12A 0.9900 . ?
C12 H12B 0.9900 . ?
C13 C14 1.538(5) . ?
C13 H13 1.0000 . ?
C14 H14A 0.9900 . ?
C14 H14B 0.9900 . ?
loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C2 C1 C3 C4 130.9(4) . . . . ?
C5 C1 C3 C4 -101.2(4) . . . . ?
C2 C1 C3 Br1 -47.9(3) . . . . ?
C5 C1 C3 Br1 80.0(4) . . . . ?
C2 C1 C5 C7 -177.9(3) . . . . ?
C3 C1 C5 C7 53.7(4) . . . . ?
C2 C1 C5 C6 60.1(4) . . . . ?
C3 C1 C5 C6 -68.3(4) . . . . ?
C2 C1 C5 C8 -60.1(3) . . . . ?
C3 C1 C5 C8 171.6(3) . . . . ?
C7 C5 C6 C11 59.9(3) . . . . ?
C8 C5 C6 C11 -58.5(4) . . . . ?
C1 C5 C6 C11 -178.0(3) . . . . ?
C6 C5 C7 C13 -58.8(3) . . . . ?
C8 C5 C7 C13 59.8(3) . . . . ?
C1 C5 C7 C13 177.2(3) . . . . ?
C7 C5 C8 C9 -59.5(4) . . . . ?
C6 C5 C8 C9 59.4(4) . . . . ?
C1 C5 C8 C9 -178.0(3) . . . . ?
C5 C8 C9 C10 -60.7(4) . . . . ?
C5 C8 C9 C14 59.9(4) . . . . ?
C14 C9 C10 C11 -59.7(4) . . . . ?
C8 C9 C10 C11 60.7(4) . . . . ?
C5 C6 C11 C12 -60.5(3) . . . . ?
C5 C6 C11 C10 59.5(4) . . . . ?
C9 C10 C11 C12 59.1(4) . . . . ?
C9 C10 C11 C6 -60.6(4) . . . . ?
C6 C11 C12 C13 60.4(3) . . . . ?
C10 C11 C12 C13 -59.8(4) . . . . ?
C11 C12 C13 C14 60.2(4) . . . . ?
C11 C12 C13 C7 -59.7(4) . . . . ?
C5 C7 C13 C12 59.0(3) . . . . ?
C5 C7 C13 C14 -60.6(4) . . . . ?
C10 C9 C14 C13 60.4(3) . . . . ?
C8 C9 C14 C13 -59.6(4) . . . . ?
C12 C13 C14 C9 -60.2(4) . . . . ?
C7 C13 C14 C9 59.9(4) . . . . ?
