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#$Date: 2024-10-04 01:13:05 +0300 (Fri, 04 Oct 2024) $
#$Revision: 295024 $
#$URL: file:///home/coder/svn-repositories/cod/cif/1/57/27/1572771.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_1572771
loop_
_publ_author_name
'Zhang, Chonghe'
'Gilliard, Robert J.'
'Cummins, Christopher'
_publ_section_title
;
 Arene extrusion as an approach to reductive elimination at boron:
 Implication of carbene-ligated haloborylene as a transient reactive
 intermediate
;
_journal_name_full               'Chemical Science'
_journal_paper_doi               10.1039/D4SC05524A
_journal_year                    2024
_chemical_formula_sum            'C23 H35 B Cl N'
_chemical_formula_weight         371.78
_space_group_crystal_system      orthorhombic
_space_group_IT_number           61
_space_group_name_Hall           '-P 2ac 2ab'
_space_group_name_H-M_alt        'P b c a'
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-2019/1
_audit_update_record
;
2023-09-26 deposited with the CCDC.	2024-10-02 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   12.0999(10)
_cell_length_b                   13.3302(10)
_cell_length_c                   25.993(2)
_cell_measurement_reflns_used    9357
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      31.05
_cell_measurement_theta_min      2.40
_cell_volume                     4192.5(6)
_computing_cell_refinement       'SAINT 8.38A (Bruker-AXS, 2017)'
_computing_data_collection       'APEX3 v2017.3.0 (Bruker-AXS, 2017)'
_computing_data_reduction        'SAINT 8.38A (Bruker-AXS, 2017)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-2019/1 (Sheldrick, 2019)'
_computing_structure_solution    'SHELXT-2015 (Sheldrick, 2015)'
_diffrn_ambient_temperature      100(2)
_diffrn_detector_area_resol_mean 7.4
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device_type  'Bruker Photon3 CPAD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0383
_diffrn_reflns_av_unetI/netI     0.0093
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_limit_h_max       17
_diffrn_reflns_limit_h_min       -17
_diffrn_reflns_limit_k_max       19
_diffrn_reflns_limit_k_min       -19
_diffrn_reflns_limit_l_max       37
_diffrn_reflns_limit_l_min       -37
_diffrn_reflns_number            277772
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         31.052
_diffrn_reflns_theta_min         1.567
_diffrn_source
'I\mS micro-focus sealed tube, multilayer optics'
_exptl_absorpt_coefficient_mu    0.189
_exptl_absorpt_correction_T_max  0.7462
_exptl_absorpt_correction_T_min  0.7150
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS (Herbst-Irmer et al., 2015)'
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.178
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       plate
_exptl_crystal_F_000             1616
_exptl_crystal_size_max          0.119
_exptl_crystal_size_mid          0.111
_exptl_crystal_size_min          0.039
_refine_diff_density_max         0.450
_refine_diff_density_min         -0.325
_refine_diff_density_rms         0.045
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.058
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     243
_refine_ls_number_reflns         6699
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.059
_refine_ls_R_factor_all          0.0355
_refine_ls_R_factor_gt           0.0327
_refine_ls_shift/su_max          0.003
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.0460P)²+1.5076P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0897
_refine_ls_wR_factor_ref         0.0924
_reflns_Friedel_coverage         0.000
_reflns_number_gt                6214
_reflns_number_total             6699
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d4sc05524a3.cif
_cod_data_source_block           5Cl
_cod_database_code               1572771
_shelx_shelxl_version_number     2019/1
_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   0.978
_shelx_estimated_absorpt_t_max   0.993
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'-x, y+1/2, -z+1/2'
'x+1/2, -y+1/2, -z'
'-x, -y, -z'
'x-1/2, y, -z-1/2'
'x, -y-1/2, z-1/2'
'-x-1/2, y-1/2, 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_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
Cl1 Cl 0.72496(2) 0.45234(2) 0.52206(2) 0.02085(6) Uani 1 1 d . . . . .
N1 N 0.57467(5) 0.23467(5) 0.61388(3) 0.01298(12) Uani 1 1 d . . . . .
B1 B 0.65534(8) 0.39618(7) 0.58163(4) 0.01628(16) Uani 1 1 d D . . . .
H1 H 0.7259(9) 0.3998(10) 0.6125(4) 0.020 Uiso 1 1 d D U . . .
C1 C 0.54958(8) 0.46695(6) 0.59681(3) 0.02009(16) Uani 1 1 d . . . . .
H1A H 0.577451 0.526838 0.615215 0.024 Uiso 1 1 calc R U . . .
H1B H 0.514411 0.490486 0.564605 0.024 Uiso 1 1 calc R U . . .
C2 C 0.45975(7) 0.41653(6) 0.63057(3) 0.01915(15) Uani 1 1 d . . . . .
H2 H 0.422925 0.364301 0.608924 0.023 Uiso 1 1 calc R U . . .
C3 C 0.37077(8) 0.49137(8) 0.64674(4) 0.0284(2) Uani 1 1 d . . . . .
H3A H 0.315449 0.457235 0.667989 0.043 Uiso 1 1 calc R U . . .
H3B H 0.335077 0.519121 0.616029 0.043 Uiso 1 1 calc R U . . .
H3C H 0.404677 0.545809 0.666561 0.043 Uiso 1 1 calc R U . . .
C4 C 0.60743(6) 0.28401(6) 0.57317(3) 0.01261(13) Uani 1 1 d . . . . .
C5 C 0.57609(6) 0.22790(6) 0.52489(3) 0.01290(13) Uani 1 1 d . . . . .
C6 C 0.52381(7) 0.12898(6) 0.54490(3) 0.01592(14) Uani 1 1 d . . . . .
H6A H 0.452934 0.115842 0.527112 0.019 Uiso 1 1 calc R U . . .
H6B H 0.574165 0.071801 0.538471 0.019 Uiso 1 1 calc R U . . .
C7 C 0.50450(7) 0.14202(6) 0.60287(3) 0.01537(14) Uani 1 1 d . . . . .
C8 C 0.38365(7) 0.16525(8) 0.61575(4) 0.02508(18) Uani 1 1 d . . . . .
H8A H 0.378027 0.186464 0.651755 0.038 Uiso 1 1 calc R U . . .
H8B H 0.338680 0.105005 0.610404 0.038 Uiso 1 1 calc R U . . .
H8C H 0.356926 0.219157 0.593335 0.038 Uiso 1 1 calc R U . . .
C9 C 0.54173(9) 0.05062(7) 0.63347(4) 0.02478(19) Uani 1 1 d . . . . .
H9A H 0.618855 0.035221 0.625110 0.037 Uiso 1 1 calc R U . . .
H9B H 0.495016 -0.006924 0.624654 0.037 Uiso 1 1 calc R U . . .
H9C H 0.535258 0.064760 0.670351 0.037 Uiso 1 1 calc R U . . .
C10 C 0.49373(7) 0.29378(6) 0.49424(3) 0.01592(14) Uani 1 1 d . . . . .
H10A H 0.425921 0.303704 0.514941 0.019 Uiso 1 1 calc R U . . .
H10B H 0.527211 0.360455 0.488041 0.019 Uiso 1 1 calc R U . . .
C11 C 0.46284(7) 0.24620(7) 0.44264(3) 0.02024(16) Uani 1 1 d . . . . .
H11A H 0.421252 0.183382 0.448810 0.024 Uiso 1 1 calc R U . . .
H11B H 0.414387 0.292554 0.423227 0.024 Uiso 1 1 calc R U . . .
C12 C 0.56588(8) 0.22317(7) 0.41081(3) 0.02262(17) Uani 1 1 d . . . . .
H12A H 0.603290 0.286706 0.401540 0.027 Uiso 1 1 calc R U . . .
H12B H 0.544032 0.188998 0.378558 0.027 Uiso 1 1 calc R U . . .
C13 C 0.64594(7) 0.15630(7) 0.44086(3) 0.02031(16) Uani 1 1 d . . . . .
H13A H 0.610418 0.090847 0.447974 0.024 Uiso 1 1 calc R U . . .
H13B H 0.712837 0.143856 0.419880 0.024 Uiso 1 1 calc R U . . .
C14 C 0.67900(7) 0.20600(6) 0.49164(3) 0.01657(14) Uani 1 1 d . . . . .
H14A H 0.718546 0.269495 0.484460 0.020 Uiso 1 1 calc R U . . .
H14B H 0.729769 0.161225 0.510745 0.020 Uiso 1 1 calc R U . . .
C15 C 0.74684(7) 0.16549(7) 0.68824(3) 0.01836(15) Uani 1 1 d . . . . .
H15 H 0.735379 0.142297 0.652042 0.022 Uiso 1 1 calc R U . . .
C16 C 0.75171(9) 0.07282(8) 0.72311(4) 0.0281(2) Uani 1 1 d . . . . .
H16A H 0.771655 0.093336 0.758104 0.042 Uiso 1 1 calc R U . . .
H16B H 0.807325 0.025955 0.709930 0.042 Uiso 1 1 calc R U . . .
H16C H 0.679282 0.039939 0.723583 0.042 Uiso 1 1 calc R U . . .
C17 C 0.85721(7) 0.22192(8) 0.69075(4) 0.02467(18) Uani 1 1 d . . . . .
H17A H 0.853773 0.281214 0.668519 0.037 Uiso 1 1 calc R U . . .
H17B H 0.916877 0.177733 0.679073 0.037 Uiso 1 1 calc R U . . .
H17C H 0.871489 0.242872 0.726277 0.037 Uiso 1 1 calc R U . . .
C18 C 0.58141(6) 0.27751(6) 0.66529(3) 0.01461(14) Uani 1 1 d . . . . .
C19 C 0.65455(7) 0.23808(6) 0.70174(3) 0.01654(14) Uani 1 1 d . . . . .
C20 C 0.65028(8) 0.27886(7) 0.75154(3) 0.02173(17) Uani 1 1 d . . . . .
H20 H 0.696471 0.251938 0.777675 0.026 Uiso 1 1 calc R U . . .
C21 C 0.58011(8) 0.35740(7) 0.76320(3) 0.02413(18) Uani 1 1 d . . . . .
H21 H 0.576503 0.382247 0.797410 0.029 Uiso 1 1 calc R U . . .
C22 C 0.51475(8) 0.40026(7) 0.72507(3) 0.02216(17) Uani 1 1 d . . . . .
H22 H 0.469081 0.456016 0.733223 0.027 Uiso 1 1 calc R U . . .
C23 C 0.51533(7) 0.36251(6) 0.67506(3) 0.01728(15) 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'
H H 0.0000 0.0000 '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'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cl Cl 0.1484 0.1585 '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
C4 N1 C18 121.91(7) . . ?
C4 N1 C7 115.10(6) . . ?
C18 N1 C7 121.39(6) . . ?
C4 B1 C1 106.55(7) . . ?
C4 B1 Cl1 114.13(6) . . ?
C1 B1 Cl1 108.26(6) . . ?
C4 B1 H1 113.0(6) . . ?
C1 B1 H1 112.3(6) . . ?
Cl1 B1 H1 102.6(6) . . ?
C2 C1 B1 115.75(7) . . ?
C2 C1 H1A 108.3 . . ?
B1 C1 H1A 108.3 . . ?
C2 C1 H1B 108.3 . . ?
B1 C1 H1B 108.3 . . ?
H1A C1 H1B 107.4 . . ?
C23 C2 C3 114.36(8) . . ?
C23 C2 C1 109.03(7) . . ?
C3 C2 C1 111.52(7) . . ?
C23 C2 H2 107.2 . . ?
C3 C2 H2 107.2 . . ?
C1 C2 H2 107.2 . . ?
C2 C3 H3A 109.5 . . ?
C2 C3 H3B 109.5 . . ?
H3A C3 H3B 109.5 . . ?
C2 C3 H3C 109.5 . . ?
H3A C3 H3C 109.5 . . ?
H3B C3 H3C 109.5 . . ?
N1 C4 C5 110.33(6) . . ?
N1 C4 B1 117.60(7) . . ?
C5 C4 B1 131.35(7) . . ?
C4 C5 C14 110.88(6) . . ?
C4 C5 C10 107.96(6) . . ?
C14 C5 C10 109.78(6) . . ?
C4 C5 C6 104.17(6) . . ?
C14 C5 C6 110.83(6) . . ?
C10 C5 C6 113.07(6) . . ?
C7 C6 C5 107.15(6) . . ?
C7 C6 H6A 110.3 . . ?
C5 C6 H6A 110.3 . . ?
C7 C6 H6B 110.3 . . ?
C5 C6 H6B 110.3 . . ?
H6A C6 H6B 108.5 . . ?
C9 C7 N1 112.64(7) . . ?
C9 C7 C8 109.27(7) . . ?
N1 C7 C8 109.06(7) . . ?
C9 C7 C6 112.16(7) . . ?
N1 C7 C6 101.01(6) . . ?
C8 C7 C6 112.51(7) . . ?
C7 C8 H8A 109.5 . . ?
C7 C8 H8B 109.5 . . ?
H8A C8 H8B 109.5 . . ?
C7 C8 H8C 109.5 . . ?
H8A C8 H8C 109.5 . . ?
H8B C8 H8C 109.5 . . ?
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 . . ?
C11 C10 C5 111.90(7) . . ?
C11 C10 H10A 109.2 . . ?
C5 C10 H10A 109.2 . . ?
C11 C10 H10B 109.2 . . ?
C5 C10 H10B 109.2 . . ?
H10A C10 H10B 107.9 . . ?
C12 C11 C10 111.02(7) . . ?
C12 C11 H11A 109.4 . . ?
C10 C11 H11A 109.4 . . ?
C12 C11 H11B 109.4 . . ?
C10 C11 H11B 109.4 . . ?
H11A C11 H11B 108.0 . . ?
C11 C12 C13 110.92(7) . . ?
C11 C12 H12A 109.5 . . ?
C13 C12 H12A 109.5 . . ?
C11 C12 H12B 109.5 . . ?
C13 C12 H12B 109.5 . . ?
H12A C12 H12B 108.0 . . ?
C14 C13 C12 110.70(7) . . ?
C14 C13 H13A 109.5 . . ?
C12 C13 H13A 109.5 . . ?
C14 C13 H13B 109.5 . . ?
C12 C13 H13B 109.5 . . ?
H13A C13 H13B 108.1 . . ?
C13 C14 C5 110.73(7) . . ?
C13 C14 H14A 109.5 . . ?
C5 C14 H14A 109.5 . . ?
C13 C14 H14B 109.5 . . ?
C5 C14 H14B 109.5 . . ?
H14A C14 H14B 108.1 . . ?
C19 C15 C16 113.90(7) . . ?
C19 C15 C17 108.53(7) . . ?
C16 C15 C17 109.65(8) . . ?
C19 C15 H15 108.2 . . ?
C16 C15 H15 108.2 . . ?
C17 C15 H15 108.2 . . ?
C15 C16 H16A 109.5 . . ?
C15 C16 H16B 109.5 . . ?
H16A C16 H16B 109.5 . . ?
C15 C16 H16C 109.5 . . ?
H16A C16 H16C 109.5 . . ?
H16B C16 H16C 109.5 . . ?
C15 C17 H17A 109.5 . . ?
C15 C17 H17B 109.5 . . ?
H17A C17 H17B 109.5 . . ?
C15 C17 H17C 109.5 . . ?
H17A C17 H17C 109.5 . . ?
H17B C17 H17C 109.5 . . ?
C19 C18 C23 122.60(7) . . ?
C19 C18 N1 120.65(7) . . ?
C23 C18 N1 116.67(7) . . ?
C18 C19 C20 117.09(8) . . ?
C18 C19 C15 123.24(7) . . ?
C20 C19 C15 119.10(7) . . ?
C21 C20 C19 121.18(8) . . ?
C21 C20 H20 119.4 . . ?
C19 C20 H20 119.4 . . ?
C20 C21 C22 120.31(8) . . ?
C20 C21 H21 119.8 . . ?
C22 C21 H21 119.8 . . ?
C21 C22 C23 120.89(8) . . ?
C21 C22 H22 119.6 . . ?
C23 C22 H22 119.6 . . ?
C22 C23 C18 117.44(8) . . ?
C22 C23 C2 122.45(8) . . ?
C18 C23 C2 119.67(7) . . ?
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
Cl1 B1 1.9150(9) . ?
N1 C4 1.3075(10) . ?
N1 C18 1.4555(10) . ?
N1 C7 1.5258(10) . ?
B1 C4 1.6186(12) . ?
B1 C1 1.6381(13) . ?
B1 H1 1.173(10) . ?
C1 C2 1.5503(12) . ?
C1 H1A 0.9900 . ?
C1 H1B 0.9900 . ?
C2 C23 1.5190(12) . ?
C2 C3 1.5267(12) . ?
C2 H2 1.0000 . ?
C3 H3A 0.9800 . ?
C3 H3B 0.9800 . ?
C3 H3C 0.9800 . ?
C4 C5 1.5093(10) . ?
C5 C14 1.5436(11) . ?
C5 C10 1.5488(11) . ?
C5 C6 1.5523(11) . ?
C6 C7 1.5347(11) . ?
C6 H6A 0.9900 . ?
C6 H6B 0.9900 . ?
C7 C9 1.5231(12) . ?
C7 C8 1.5317(12) . ?
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 C11 1.5301(11) . ?
C10 H10A 0.9900 . ?
C10 H10B 0.9900 . ?
C11 C12 1.5276(13) . ?
C11 H11A 0.9900 . ?
C11 H11B 0.9900 . ?
C12 C13 1.5307(13) . ?
C12 H12A 0.9900 . ?
C12 H12B 0.9900 . ?
C13 C14 1.5303(12) . ?
C13 H13A 0.9900 . ?
C13 H13B 0.9900 . ?
C14 H14A 0.9900 . ?
C14 H14B 0.9900 . ?
C15 C19 1.5187(12) . ?
C15 C16 1.5334(13) . ?
C15 C17 1.5342(13) . ?
C15 H15 1.0000 . ?
C16 H16A 0.9800 . ?
C16 H16B 0.9800 . ?
C16 H16C 0.9800 . ?
C17 H17A 0.9800 . ?
C17 H17B 0.9800 . ?
C17 H17C 0.9800 . ?
C18 C19 1.3989(11) . ?
C18 C23 1.4099(11) . ?
C19 C20 1.4051(12) . ?
C20 C21 1.3816(14) . ?
C20 H20 0.9500 . ?
C21 C22 1.3907(14) . ?
C21 H21 0.9500 . ?
C22 C23 1.3941(12) . ?
C22 H22 0.9500 . ?
