#------------------------------------------------------------------------------
#$Date: 2016-03-21 13:05:55 +0100 (lun 21 de mar de 2016) $
#$Revision: 178710 $
#$URL: svn://www.crystallography.net/cod/cif/4/08/21/4082147.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_4082147
loop_
_publ_author_name
'Boussonnière, Anne'
'Pan, Xiangcheng'
'Geib, Steven J.'
'Curran, Dennis P.'
_publ_section_title
;
 Borenium-Catalyzed Hydroborations of Silyl-Substituted Alkenes and
 Alkynes with a Readily Available N-Heterocyclic Carbene--Borane
;
_journal_issue                   24
_journal_name_full               Organometallics
_journal_page_first              7445
_journal_paper_doi               10.1021/om400932g
_journal_volume                  32
_journal_year                    2013
_chemical_absolute_configuration ad
_chemical_formula_sum            'C16 H25 B N2 Si'
_chemical_formula_weight         284.28
_chemical_name_systematic
;
 ?
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           9
_space_group_name_Hall           'C -2yc'
_space_group_name_H-M_alt        'C 1 c 1'
_symmetry_space_group_name_Hall  'C -2yc'
_symmetry_space_group_name_H-M   'C 1 c 1'
_atom_sites_solution_hydrogens   mixed
_audit_creation_method           SHELXL-2013
_cell_angle_alpha                90
_cell_angle_beta                 113.586(6)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   19.300(3)
_cell_length_b                   7.7161(10)
_cell_length_c                   12.3941(17)
_cell_measurement_temperature    173(2)
_cell_volume                     1691.5(4)
_computing_structure_refinement  'SHELXL-2013 (Sheldrick, 2013)'
_diffrn_ambient_temperature      173(2)
_diffrn_measured_fraction_theta_full 0.976
_diffrn_measured_fraction_theta_max 0.975
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.0661
_diffrn_reflns_av_unetI/netI     0.0746
_diffrn_reflns_Laue_measured_fraction_full 0.976
_diffrn_reflns_Laue_measured_fraction_max 0.975
_diffrn_reflns_limit_h_max       21
_diffrn_reflns_limit_h_min       -23
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            12873
_diffrn_reflns_point_group_measured_fraction_full 0.976
_diffrn_reflns_point_group_measured_fraction_max 0.975
_diffrn_reflns_theta_full        67.679
_diffrn_reflns_theta_max         68.428
_diffrn_reflns_theta_min         5.001
_exptl_absorpt_coefficient_mu    1.138
_exptl_absorpt_correction_T_max  0.876
_exptl_absorpt_correction_T_min  0.788
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'Bruker Sadabs'
_exptl_crystal_density_diffrn    1.116
_exptl_crystal_F_000             616
_exptl_crystal_size_max          0.220
_exptl_crystal_size_mid          0.140
_exptl_crystal_size_min          0.120
_refine_diff_density_max         1.046
_refine_diff_density_min         -1.542
_refine_diff_density_rms         0.154
_refine_ls_abs_structure_details
;
 Refined as an inversion twin.
;
_refine_ls_abs_structure_Flack   0.07(5)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.709
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     190
_refine_ls_number_reflns         2725
_refine_ls_number_restraints     2
_refine_ls_restrained_S_all      1.709
_refine_ls_R_factor_all          0.1302
_refine_ls_R_factor_gt           0.0362
_refine_ls_shift/su_max          0.019
_refine_ls_shift/su_mean         0.002
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.0782P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1052
_refine_ls_wR_factor_ref         0.1637
_reflns_Friedel_coverage         0.997
_reflns_Friedel_fraction_full    0.977
_reflns_Friedel_fraction_max     0.975
_reflns_number_gt                2164
_reflns_number_total             2725
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            om400932g_si_002.cif
_cod_data_source_block           xp_0521
_cod_original_cell_volume        1691.6(4)
_cod_database_code               4082147
#BEGIN Tags that were not found in dictionaries:
_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   0.788
_shelx_estimated_absorpt_t_max   0.876
_shelxl_version_number           2013-3
#END Tags that were not found in dictionaries
loop_
_space_group_symop_operation_xyz
'x, y, z'
'x, -y, z+1/2'
'x+1/2, y+1/2, z'
'x+1/2, -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
Si1 Si 0.47927(5) 0.09484(16) 0.21458(8) 0.0264(4) Uani 1 1 d . .
N1 N 0.7034(2) 0.5774(6) 0.3034(4) 0.0303(11) Uani 1 1 d . .
B1 B 0.6145(2) 0.2977(8) 0.2530(4) 0.0278(12) Uani 1 1 d . .
H1B H 0.625(3) 0.187(10) 0.193(6) 0.07(2) Uiso 1 1 d . .
H2B H 0.647(2) 0.264(7) 0.347(4) 0.026(12) Uiso 1 1 d . .
C1 C 0.6484(2) 0.4757(6) 0.2282(4) 0.0275(11) Uani 1 1 d . .
N2 N 0.6274(2) 0.5566(6) 0.1230(4) 0.0334(11) Uani 1 1 d . .
C2 C 0.7153(2) 0.7198(7) 0.2466(5) 0.0352(12) Uani 1 1 d . .
H2A H 0.7506 0.8103 0.2810 0.042 Uiso 1 1 calc R U
C3 C 0.6675(2) 0.7068(8) 0.1333(5) 0.0362(13) Uani 1 1 d . .
H3A H 0.6623 0.7862 0.0720 0.043 Uiso 1 1 calc R U
C4 C 0.7469(3) 0.5386(8) 0.4282(5) 0.0441(15) Uani 1 1 d . .
H4A H 0.7283 0.4308 0.4488 0.066 Uiso 1 1 calc R U
H4B H 0.7411 0.6337 0.4763 0.066 Uiso 1 1 calc R U
H4C H 0.8005 0.5256 0.4428 0.066 Uiso 1 1 calc R U
C5 C 0.5685(3) 0.4954(9) 0.0127(5) 0.0477(16) Uani 1 1 d . .
H5A H 0.5480 0.3853 0.0264 0.072 Uiso 1 1 calc R U
H5B H 0.5901 0.4785 -0.0459 0.072 Uiso 1 1 calc R U
H5C H 0.5279 0.5816 -0.0164 0.072 Uiso 1 1 calc R U
C6 C 0.52417(19) 0.3128(7) 0.2206(4) 0.0267(11) Uani 1 1 d . .
C7 C 0.4885(2) 0.4645(7) 0.2054(4) 0.0272(12) Uani 1 1 d . .
H7A H 0.5203 0.5635 0.2205 0.033 Uiso 1 1 calc R U
C8 C 0.5484(2) -0.0438(7) 0.3340(5) 0.0335(12) Uani 1 1 d . .
H8A H 0.5263 -0.1586 0.3326 0.050 Uiso 1 1 calc R U
H8B H 0.5600 0.0107 0.4106 0.050 Uiso 1 1 calc R U
H8C H 0.5950 -0.0560 0.3208 0.050 Uiso 1 1 calc R U
C9 C 0.4618(3) -0.0138(8) 0.0727(5) 0.0437(15) Uani 1 1 d . .
H9A H 0.4259 0.0550 0.0079 0.066 Uiso 1 1 calc R U
H9B H 0.4406 -0.1294 0.0724 0.066 Uiso 1 1 calc R U
H9C H 0.5095 -0.0244 0.0628 0.066 Uiso 1 1 calc R U
C10 C 0.3898(2) 0.0988(7) 0.2391(5) 0.0324(13) Uani 1 1 d . .
H10A H 0.3522 0.1705 0.1785 0.049 Uiso 1 1 calc R U
H10B H 0.3999 0.1474 0.3170 0.049 Uiso 1 1 calc R U
H10C H 0.3704 -0.0195 0.2346 0.049 Uiso 1 1 calc R U
C11 C 0.3797(2) 0.5941(6) 0.2400(4) 0.0292(13) Uani 1 1 d . .
H11A H 0.4143 0.6329 0.3149 0.035 Uiso 1 1 calc R U
C12 C 0.3032(2) 0.6301(7) 0.2044(5) 0.0360(13) Uani 1 1 d . .
H12A H 0.2858 0.6907 0.2555 0.043 Uiso 1 1 calc R U
C13 C 0.2527(2) 0.5780(7) 0.0952(5) 0.0354(14) Uani 1 1 d . .
H13A H 0.2004 0.6029 0.0709 0.042 Uiso 1 1 calc R U
C14 C 0.2776(2) 0.4899(7) 0.0207(5) 0.0341(13) Uani 1 1 d . .
H14A H 0.2427 0.4555 -0.0552 0.041 Uiso 1 1 calc R U
C15 C 0.3541(2) 0.4514(7) 0.0572(4) 0.0295(11) Uani 1 1 d . .
H15A H 0.3710 0.3894 0.0060 0.035 Uiso 1 1 calc R U
C16 C 0.4067(2) 0.5026(6) 0.1683(4) 0.0265(11) Uani 1 1 d . .
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 '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'
B B 0.0090 0.0039 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Si Si 0.2541 0.3302 '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
C9 Si1 C10 109.4(2)
C9 Si1 C6 110.4(3)
C10 Si1 C6 114.9(2)
C9 Si1 C8 107.0(3)
C10 Si1 C8 107.0(2)
C6 Si1 C8 107.9(2)
C1 N1 C2 110.9(4)
C1 N1 C4 124.8(5)
C2 N1 C4 124.2(4)
C1 B1 C6 111.7(4)
C1 B1 H1B 108(4)
C6 B1 H1B 109(3)
C1 B1 H2B 107(3)
C6 B1 H2B 112(2)
H1B B1 H2B 109(4)
N1 C1 N2 104.3(4)
N1 C1 B1 129.4(4)
N2 C1 B1 126.3(4)
C1 N2 C3 111.1(4)
C1 N2 C5 125.0(4)
C3 N2 C5 123.9(5)
C3 C2 N1 106.9(4)
C3 C2 H2A 126.5
N1 C2 H2A 126.5
C2 C3 N2 106.7(5)
C2 C3 H3A 126.7
N2 C3 H3A 126.7
N1 C4 H4A 109.5
N1 C4 H4B 109.5
H4A C4 H4B 109.5
N1 C4 H4C 109.5
H4A C4 H4C 109.5
H4B C4 H4C 109.5
N2 C5 H5A 109.5
N2 C5 H5B 109.5
H5A C5 H5B 109.5
N2 C5 H5C 109.5
H5A C5 H5C 109.5
H5B C5 H5C 109.5
C7 C6 B1 122.6(4)
C7 C6 Si1 125.2(3)
B1 C6 Si1 112.2(3)
C6 C7 C16 129.9(5)
C6 C7 H7A 115.0
C16 C7 H7A 115.0
Si1 C8 H8A 109.5
Si1 C8 H8B 109.5
H8A C8 H8B 109.5
Si1 C8 H8C 109.5
H8A C8 H8C 109.5
H8B C8 H8C 109.5
Si1 C9 H9A 109.5
Si1 C9 H9B 109.5
H9A C9 H9B 109.5
Si1 C9 H9C 109.5
H9A C9 H9C 109.5
H9B C9 H9C 109.5
Si1 C10 H10A 109.5
Si1 C10 H10B 109.5
H10A C10 H10B 109.5
Si1 C10 H10C 109.5
H10A C10 H10C 109.5
H10B C10 H10C 109.5
C16 C11 C12 121.4(4)
C16 C11 H11A 119.3
C12 C11 H11A 119.3
C13 C12 C11 120.0(5)
C13 C12 H12A 120.0
C11 C12 H12A 120.0
C12 C13 C14 120.2(4)
C12 C13 H13A 119.9
C14 C13 H13A 119.9
C15 C14 C13 119.8(5)
C15 C14 H14A 120.1
C13 C14 H14A 120.1
C14 C15 C16 121.0(5)
C14 C15 H15A 119.5
C16 C15 H15A 119.5
C11 C16 C15 117.6(4)
C11 C16 C7 121.8(4)
C15 C16 C7 120.6(4)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
Si1 C9 1.853(6)
Si1 C10 1.870(5)
Si1 C6 1.879(5)
Si1 C8 1.880(5)
N1 C1 1.349(6)
N1 C2 1.373(7)
N1 C4 1.465(7)
B1 C1 1.603(8)
B1 C6 1.629(5)
B1 H1B 1.20(8)
B1 H2B 1.11(5)
C1 N2 1.352(7)
N2 C3 1.371(7)
N2 C5 1.463(6)
C2 C3 1.340(7)
C2 H2A 0.9500
C3 H3A 0.9500
C4 H4A 0.9800
C4 H4B 0.9800
C4 H4C 0.9800
C5 H5A 0.9800
C5 H5B 0.9800
C5 H5C 0.9800
C6 C7 1.332(7)
C7 C16 1.488(5)
C7 H7A 0.9500
C8 H8A 0.9800
C8 H8B 0.9800
C8 H8C 0.9800
C9 H9A 0.9800
C9 H9B 0.9800
C9 H9C 0.9800
C10 H10A 0.9800
C10 H10B 0.9800
C10 H10C 0.9800
C11 C16 1.389(8)
C11 C12 1.389(6)
C11 H11A 0.9500
C12 C13 1.374(8)
C12 H12A 0.9500
C13 C14 1.379(8)
C13 H13A 0.9500
C14 C15 1.392(6)
C14 H14A 0.9500
C15 C16 1.400(6)
C15 H15A 0.9500
