#------------------------------------------------------------------------------
#$Date: 2025-01-10 10:08:49 +0200 (Fri, 10 Jan 2025) $
#$Revision: 297258 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/13/41/7134155.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_7134155
loop_
_publ_author_name
'Müller, Matthias'
'Maichle-Mössmer, Cäcilia'
'Bettinger, Holger F.'
_publ_section_title
;
 C--H functionalization of tetramethylsilane employing a borylnitrene
;
_journal_coden_ASTM              CHCOFS
_journal_issue                   100
_journal_name_full
;
 Chemical Communications (Cambridge, United Kingdom)
;
_journal_page_first              11773
_journal_page_last               11775
_journal_paper_doi               10.1039/c3cc47753c
_journal_volume                  49
_journal_year                    2013
_chemical_formula_sum            'C16 H35 B2 N O4 Si'
_chemical_formula_weight         355.16
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_symmetry_cell_setting           triclinic
_symmetry_space_group_name_H-M   'P -1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_block_doi                 10.5517/cc10rffm
_audit_creation_method           SHELXL-97
_audit_update_record
;
2013-06-20 deposited with the CCDC.	2024-11-26 downloaded from the CCDC.
;
_cell_angle_alpha                107.567(4)
_cell_angle_beta                 97.679(5)
_cell_angle_gamma                102.186(4)
_cell_formula_units_Z            2
_cell_length_a                   6.6093(14)
_cell_length_b                   10.898(2)
_cell_length_c                   15.669(3)
_cell_measurement_reflns_used    8687
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      56.71
_cell_measurement_theta_min      5.580
_cell_volume                     1027.9(4)
_computing_cell_refinement       SAINT
_computing_data_collection       COSMO
_computing_data_reduction        SAINT
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      100(2)
_diffrn_measured_fraction_theta_full 0.995
_diffrn_measured_fraction_theta_max 0.995
_diffrn_measurement_device_type  'APEX II DUO'
_diffrn_measurement_method       omega-scans
_diffrn_radiation_monochromator  multilayer
_diffrn_radiation_source         'Imus-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0349
_diffrn_reflns_av_sigmaI/netI    0.0303
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_number            19057
_diffrn_reflns_theta_full        28.41
_diffrn_reflns_theta_max         28.41
_diffrn_reflns_theta_min         1.39
_exptl_absorpt_coefficient_mu    0.132
_exptl_absorpt_correction_T_max  0.9799
_exptl_absorpt_correction_T_min  0.9209
_exptl_absorpt_correction_type   numerical
_exptl_absorpt_process_details   sadabs
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.148
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       needle
_exptl_crystal_F_000             388
_exptl_crystal_size_max          0.45
_exptl_crystal_size_mid          0.13
_exptl_crystal_size_min          0.11
_refine_diff_density_max         0.475
_refine_diff_density_min         -0.382
_refine_diff_density_rms         0.051
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.017
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     228
_refine_ls_number_reflns         5139
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.017
_refine_ls_R_factor_all          0.0416
_refine_ls_R_factor_gt           0.0373
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0428P)²+0.5993P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0964
_refine_ls_wR_factor_ref         0.0993
_reflns_number_gt                4596
_reflns_number_total             5139
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            c3cc47753c2.cif
_cod_data_source_block           mo_mmf572_0m
_cod_original_cell_volume        1027.8(4)
_cod_original_sg_symbol_H-M      P-1
_cod_database_code               7134155
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -z'
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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C -0.06645(19) 0.52665(11) 0.71002(8) 0.0126(2) Uani 1 1 d . . .
C2 C 0.17180(19) 0.58412(11) 0.71127(8) 0.0128(2) Uani 1 1 d . . .
C3 C -0.1876(2) 0.40967(12) 0.62489(9) 0.0186(3) Uani 1 1 d . . .
H3A H -0.3319 0.3766 0.6321 0.028 Uiso 1 1 calc R . .
H3B H -0.1159 0.3381 0.6162 0.028 Uiso 1 1 calc R . .
H3C H -0.1931 0.4387 0.5714 0.028 Uiso 1 1 calc R . .
C4 C -0.0981(2) 0.49373(13) 0.79617(9) 0.0170(2) Uani 1 1 d . . .
H4A H -0.0138 0.5686 0.8504 0.025 Uiso 1 1 calc R . .
H4B H -0.0526 0.4132 0.7944 0.025 Uiso 1 1 calc R . .
H4C H -0.2482 0.4783 0.7990 0.025 Uiso 1 1 calc R . .
C5 C 0.2126(2) 0.57438(13) 0.61614(9) 0.0186(3) Uani 1 1 d . . .
H5A H 0.1131 0.6113 0.5860 0.028 Uiso 1 1 calc R . .
H5B H 0.1929 0.4806 0.5796 0.028 Uiso 1 1 calc R . .
H5C H 0.3580 0.6251 0.6218 0.028 Uiso 1 1 calc R . .
C6 C 0.3259(2) 0.52784(12) 0.75868(9) 0.0179(2) Uani 1 1 d . . .
H6A H 0.4703 0.5675 0.7546 0.027 Uiso 1 1 calc R . .
H6B H 0.2902 0.4307 0.7288 0.027 Uiso 1 1 calc R . .
H6C H 0.3168 0.5489 0.8232 0.027 Uiso 1 1 calc R . .
C7 C 0.43599(18) 1.16149(11) 0.91360(8) 0.0127(2) Uani 1 1 d . . .
C8 C 0.24473(18) 1.20515(11) 0.95029(8) 0.0119(2) Uani 1 1 d . . .
C9 C 0.5093(2) 1.22702(13) 0.84548(9) 0.0196(3) Uani 1 1 d . . .
H9A H 0.6082 1.1828 0.8153 0.029 Uiso 1 1 calc R . .
H9B H 0.5804 1.3218 0.8781 0.029 Uiso 1 1 calc R . .
H9C H 0.3865 1.2185 0.7994 0.029 Uiso 1 1 calc R . .
C10 C 0.6244(2) 1.17783(13) 0.98711(9) 0.0186(3) Uani 1 1 d . . .
H10A H 0.5795 1.1258 1.0257 0.028 Uiso 1 1 calc R . .
H10B H 0.6804 1.2723 1.0249 0.028 Uiso 1 1 calc R . .
H10C H 0.7348 1.1459 0.9581 0.028 Uiso 1 1 calc R . .
C11 C 0.2413(2) 1.34791(12) 0.96139(9) 0.0174(2) Uani 1 1 d . . .
H11A H 0.2479 1.3628 0.9031 0.026 Uiso 1 1 calc R . .
H11B H 0.3634 1.4096 1.0085 0.026 Uiso 1 1 calc R . .
H11C H 0.1103 1.3635 0.9798 0.026 Uiso 1 1 calc R . .
C12 C 0.2163(2) 1.17625(12) 1.03809(8) 0.0159(2) Uani 1 1 d . . .
H12A H 0.0801 1.1889 1.0517 0.024 Uiso 1 1 calc R . .
H12B H 0.3313 1.2374 1.0889 0.024 Uiso 1 1 calc R . .
H12C H 0.2192 1.0839 1.0300 0.024 Uiso 1 1 calc R . .
C13 C -0.24364(18) 0.89007(12) 0.75151(8) 0.0127(2) Uani 1 1 d . . .
H13A H -0.2719 0.9630 0.8001 0.015 Uiso 1 1 calc R . .
H13B H -0.3442 0.8052 0.7459 0.015 Uiso 1 1 calc R . .
C14 C -0.0903(2) 1.07879(13) 0.64875(10) 0.0221(3) Uani 1 1 d . . .
H14A H 0.0534 1.0695 0.6631 0.033 Uiso 1 1 calc R . .
H14B H -0.1091 1.1538 0.6976 0.033 Uiso 1 1 calc R . .
H14C H -0.1122 1.0953 0.5905 0.033 Uiso 1 1 calc R . .
C15 C -0.5646(2) 0.93595(15) 0.61249(10) 0.0231(3) Uani 1 1 d . . .
H15A H -0.5794 1.0168 0.6573 0.035 Uiso 1 1 calc R . .
H15B H -0.6645 0.8576 0.6154 0.035 Uiso 1 1 calc R . .
H15C H -0.5950 0.9410 0.5509 0.035 Uiso 1 1 calc R . .
C16 C -0.2441(2) 0.78220(13) 0.54524(9) 0.0208(3) Uani 1 1 d . . .
H16A H -0.2702 0.7989 0.4872 0.031 Uiso 1 1 calc R . .
H16B H -0.3416 0.6977 0.5401 0.031 Uiso 1 1 calc R . .
H16C H -0.0978 0.7770 0.5592 0.031 Uiso 1 1 calc R . .
N1 N -0.02141(15) 0.88247(9) 0.77804(7) 0.01121(19) Uani 1 1 d . . .
O1 O -0.15276(13) 0.63956(8) 0.71207(6) 0.01296(17) Uani 1 1 d . . .
O2 O 0.20870(13) 0.72551(8) 0.76316(6) 0.01304(17) Uani 1 1 d . . .
O3 O 0.06563(13) 1.11584(8) 0.87792(6) 0.01257(17) Uani 1 1 d . . .
O4 O 0.34341(13) 1.01943(8) 0.86259(6) 0.01328(17) Uani 1 1 d . . .
B1 B 0.0144(2) 0.75310(13) 0.75179(9) 0.0118(2) Uani 1 1 d . . .
B2 B 0.1285(2) 1.00257(13) 0.83765(9) 0.0118(2) Uani 1 1 d . . .
Si1 Si -0.28725(5) 0.92159(3) 0.63917(2) 0.01364(9) 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 0.0033 0.0016 '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'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
B B 0.0013 0.0007 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Si Si 0.0817 0.0704 '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'
loop_
_citation_id
_citation_doi
_citation_year
1 10.1039/C3CC47753C 2013
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
O1 C1 C3 108.23(9) . .
O1 C1 C4 107.33(9) . .
C3 C1 C4 110.48(10) . .
O1 C1 C2 102.17(9) . .
C3 C1 C2 115.30(10) . .
C4 C1 C2 112.62(10) . .
O2 C2 C6 109.04(9) . .
O2 C2 C5 107.07(9) . .
C6 C2 C5 109.84(10) . .
O2 C2 C1 102.32(9) . .
C6 C2 C1 115.16(10) . .
C5 C2 C1 112.80(10) . .
C1 C3 H3A 109.5 . .
C1 C3 H3B 109.5 . .
H3A C3 H3B 109.5 . .
C1 C3 H3C 109.5 . .
H3A C3 H3C 109.5 . .
H3B C3 H3C 109.5 . .
C1 C4 H4A 109.5 . .
C1 C4 H4B 109.5 . .
H4A C4 H4B 109.5 . .
C1 C4 H4C 109.5 . .
H4A C4 H4C 109.5 . .
H4B C4 H4C 109.5 . .
C2 C5 H5A 109.5 . .
C2 C5 H5B 109.5 . .
H5A C5 H5B 109.5 . .
C2 C5 H5C 109.5 . .
H5A C5 H5C 109.5 . .
H5B C5 H5C 109.5 . .
C2 C6 H6A 109.5 . .
C2 C6 H6B 109.5 . .
H6A C6 H6B 109.5 . .
C2 C6 H6C 109.5 . .
H6A C6 H6C 109.5 . .
H6B C6 H6C 109.5 . .
O4 C7 C10 108.94(9) . .
O4 C7 C9 107.21(9) . .
C10 C7 C9 109.95(11) . .
O4 C7 C8 102.12(9) . .
C10 C7 C8 114.99(10) . .
C9 C7 C8 113.01(10) . .
O3 C8 C11 108.25(9) . .
O3 C8 C12 107.33(9) . .
C11 C8 C12 110.37(10) . .
O3 C8 C7 101.97(9) . .
C11 C8 C7 115.56(10) . .
C12 C8 C7 112.63(10) . .
C7 C9 H9A 109.5 . .
C7 C9 H9B 109.5 . .
H9A C9 H9B 109.5 . .
C7 C9 H9C 109.5 . .
H9A C9 H9C 109.5 . .
H9B C9 H9C 109.5 . .
C7 C10 H10A 109.5 . .
C7 C10 H10B 109.5 . .
H10A C10 H10B 109.5 . .
C7 C10 H10C 109.5 . .
H10A C10 H10C 109.5 . .
H10B C10 H10C 109.5 . .
C8 C11 H11A 109.5 . .
C8 C11 H11B 109.5 . .
H11A C11 H11B 109.5 . .
C8 C11 H11C 109.5 . .
H11A C11 H11C 109.5 . .
H11B C11 H11C 109.5 . .
C8 C12 H12A 109.5 . .
C8 C12 H12B 109.5 . .
H12A C12 H12B 109.5 . .
C8 C12 H12C 109.5 . .
H12A C12 H12C 109.5 . .
H12B C12 H12C 109.5 . .
N1 C13 Si1 111.12(8) . .
N1 C13 H13A 109.4 . .
Si1 C13 H13A 109.4 . .
N1 C13 H13B 109.4 . .
Si1 C13 H13B 109.4 . .
H13A C13 H13B 108.0 . .
Si1 C14 H14A 109.5 . .
Si1 C14 H14B 109.5 . .
H14A C14 H14B 109.5 . .
Si1 C14 H14C 109.5 . .
H14A C14 H14C 109.5 . .
H14B C14 H14C 109.5 . .
Si1 C15 H15A 109.5 . .
Si1 C15 H15B 109.5 . .
H15A C15 H15B 109.5 . .
Si1 C15 H15C 109.5 . .
H15A C15 H15C 109.5 . .
H15B C15 H15C 109.5 . .
Si1 C16 H16A 109.5 . .
Si1 C16 H16B 109.5 . .
H16A C16 H16B 109.5 . .
Si1 C16 H16C 109.5 . .
H16A C16 H16C 109.5 . .
H16B C16 H16C 109.5 . .
B1 N1 B2 125.51(10) . .
B1 N1 C13 116.98(10) . .
B2 N1 C13 116.92(9) . .
B1 O1 C1 106.56(9) . .
B1 O2 C2 106.20(9) . .
B2 O3 C8 106.05(9) . .
B2 O4 C7 106.37(9) . .
O2 B1 O1 113.11(10) . .
O2 B1 N1 125.97(11) . .
O1 B1 N1 120.92(11) . .
O4 B2 O3 113.15(10) . .
O4 B2 N1 125.67(11) . .
O3 B2 N1 121.17(11) . .
C16 Si1 C14 107.58(7) . .
C16 Si1 C15 110.17(6) . .
C14 Si1 C15 110.73(7) . .
C16 Si1 C13 110.35(6) . .
C14 Si1 C13 109.24(6) . .
C15 Si1 C13 108.76(6) . .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
C1 O1 1.4553(13) .
C1 C3 1.5174(17) .
C1 C4 1.5267(17) .
C1 C2 1.5621(17) .
C2 O2 1.4584(14) .
C2 C6 1.5173(16) .
C2 C5 1.5264(17) .
C3 H3A 0.9800 .
C3 H3B 0.9800 .
C3 H3C 0.9800 .
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 H6A 0.9800 .
C6 H6B 0.9800 .
C6 H6C 0.9800 .
C7 O4 1.4603(14) .
C7 C10 1.5192(17) .
C7 C9 1.5285(17) .
C7 C8 1.5614(16) .
C8 O3 1.4570(14) .
C8 C11 1.5178(16) .
C8 C12 1.5272(16) .
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 H11A 0.9800 .
C11 H11B 0.9800 .
C11 H11C 0.9800 .
C12 H12A 0.9800 .
C12 H12B 0.9800 .
C12 H12C 0.9800 .
C13 N1 1.4987(15) .
C13 Si1 1.8896(13) .
C13 H13A 0.9900 .
C13 H13B 0.9900 .
C14 Si1 1.8715(14) .
C14 H14A 0.9800 .
C14 H14B 0.9800 .
C14 H14C 0.9800 .
C15 Si1 1.8751(14) .
C15 H15A 0.9800 .
C15 H15B 0.9800 .
C15 H15C 0.9800 .
C16 Si1 1.8711(13) .
C16 H16A 0.9800 .
C16 H16B 0.9800 .
C16 H16C 0.9800 .
N1 B1 1.4247(16) .
N1 B2 1.4264(16) .
O1 B1 1.3831(16) .
O2 B1 1.3805(15) .
O3 B2 1.3826(15) .
O4 B2 1.3789(16) .
