#------------------------------------------------------------------------------
#$Date: 2020-07-06 04:44:48 +0300 (Mon, 06 Jul 2020) $
#$Revision: 253776 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/12/65/7126542.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_7126542
loop_
_publ_author_name
'Chen, Yu'
'Quan, Yangjian'
'Xie, Zuowei'
_publ_section_title
;
 Ir-catalyzed selective dehydrogenative cross-coupling of aryls with
 o-carboranes via a mixed directing-group strategy.
;
_journal_issue                   51
_journal_name_full
'Chemical communications (Cambridge, England)'
_journal_page_first              7001
_journal_page_last               7004
_journal_paper_doi               10.1039/d0cc02531c
_journal_volume                  56
_journal_year                    2020
_chemical_formula_sum            'C17 H23.25 B10 N'
_chemical_formula_weight         349.71
_space_group_crystal_system      orthorhombic
_space_group_IT_number           62
_space_group_name_Hall           '-P 2ac 2n'
_space_group_name_H-M_alt        'P n m a'
_atom_sites_solution_hydrogens   geom
_audit_creation_method           SHELXL-2014/6
_audit_update_record
;
2020-03-02 deposited with the CCDC.	2020-05-15 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   10.6954(6)
_cell_length_b                   10.2783(6)
_cell_length_c                   18.0417(9)
_cell_measurement_reflns_used    260
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      15
_cell_measurement_theta_min      15
_cell_volume                     1983.33(19)
_computing_cell_refinement       'BRUKER D8VENTURE DIFFRACTOMETER'
_computing_data_collection       'BRUKER D8VENTURE DIFFRACTOMETER'
_computing_data_reduction        'BRUKER D8VENTURE DIFFRACTOMETER'
_computing_molecular_graphics    'BRUKER SHELXTL'
_computing_publication_material  'BRUKER SHELXTL'
_computing_structure_refinement  'SHELXL-2014/6 (Sheldrick, 2014)'
_diffrn_ambient_temperature      296(2)
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_device_type  'BRUKER D8VENTURE DIFFRACTOMETER'
_diffrn_measurement_method       'PHI & OMEGA SCAN'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0470
_diffrn_reflns_av_unetI/netI     0.0163
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_number            44175
_diffrn_reflns_point_group_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         25.248
_diffrn_reflns_theta_min         2.214
_exptl_absorpt_coefficient_mu    0.060
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_correction_T_min  0.6349
_exptl_absorpt_correction_type   multi-scan
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.171
_exptl_crystal_description       block
_exptl_crystal_F_000             729
_exptl_crystal_size_max          0.500
_exptl_crystal_size_mid          0.400
_exptl_crystal_size_min          0.300
_refine_diff_density_max         0.423
_refine_diff_density_min         -0.540
_refine_diff_density_rms         0.066
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.096
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     148
_refine_ls_number_reflns         1899
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.096
_refine_ls_R_factor_all          0.0941
_refine_ls_R_factor_gt           0.0797
_refine_ls_shift/su_max          0.003
_refine_ls_shift/su_mean         0.001
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.1517P)²+0.9328P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2376
_refine_ls_wR_factor_ref         0.2543
_reflns_Friedel_coverage         0.000
_reflns_number_gt                1517
_reflns_number_total             1899
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d0cc02531c2.cif
_cod_data_source_block           3at
_cod_depositor_comments
'Adding full bibliography for 7126537--7126543.cif.'
_cod_database_code               7126542
_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   0.971
_shelx_estimated_absorpt_t_max   0.982
_shelxl_version_number           2014/6
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'-x, y+1/2, -z'
'x+1/2, -y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, y, -z-1/2'
'x, -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
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
N1 N 0.6323(2) 0.1415(2) 0.61956(13) 0.0549(7) Uani 0.5 1 d . . P . .
C22 C 0.6323(2) 0.1415(2) 0.61956(13) 0.0549(7) Uani 0.5 1 d . . P . .
C1 C 0.7285(3) 0.2500 0.46364(18) 0.0433(8) Uani 1 2 d S T P . .
H1 H 0.6977 0.2500 0.5218 0.052 Uiso 1 2 calc R U P . .
C2 C 0.8305(3) 0.1655(3) 0.41354(17) 0.0583(8) Uani 0.5 1 d . . P . .
B9 B 0.8305(3) 0.1655(3) 0.41354(17) 0.0583(8) Uani 0.5 1 d . . P . .
C11 C 0.9221(5) 0.0884(7) 0.4526(4) 0.0686(16) Uani 0.5 1 d . . P . .
H11A H 0.9750 0.0448 0.4175 0.103 Uiso 0.5 1 calc R U P . .
H11B H 0.9721 0.1440 0.4834 0.103 Uiso 0.5 1 calc R U P . .
H11C H 0.8803 0.0251 0.4828 0.103 Uiso 0.5 1 calc R U P . .
C12 C 0.4569(3) 0.2500 0.47669(19) 0.0469(9) Uani 1 2 d S T P . .
C13 C 0.3449(4) 0.2500 0.4389(2) 0.0646(11) Uani 1 2 d S T P . .
H13A H 0.3458 0.2500 0.3873 0.077 Uiso 1 2 calc R U P . .
C14 C 0.2309(4) 0.2500 0.4754(3) 0.0754(14) Uani 1 2 d S T P . .
H14A H 0.1568 0.2500 0.4484 0.091 Uiso 1 2 calc R U P . .
C15 C 0.2272(4) 0.2500 0.5504(3) 0.0669(12) Uani 1 2 d S T P . .
H15A H 0.1506 0.2500 0.5748 0.080 Uiso 1 2 calc R U P . .
C16 C 0.3357(4) 0.2500 0.5906(2) 0.0593(10) Uani 1 2 d S T P . .
H16A H 0.3324 0.2500 0.6421 0.071 Uiso 1 2 calc R U P . .
C17 C 0.4514(3) 0.2500 0.5546(2) 0.0458(8) Uani 1 2 d S T P . .
C18 C 0.5671(3) 0.2500 0.59949(19) 0.0490(9) Uani 1 2 d S T P . .
C19 C 0.7462(2) 0.1817(3) 0.65234(13) 0.0555(7) Uani 1 1 d . . . . .
C20 C 0.8488(3) 0.1130(5) 0.67900(18) 0.0894(13) Uani 1 1 d . . . . .
H20A H 0.8495 0.0225 0.6795 0.107 Uiso 1 1 calc R U . . .
C21 C 0.9488(3) 0.1832(5) 0.70453(18) 0.129(3) Uani 1 1 d . . . . .
H21 H 1.0185 0.1392 0.7224 0.155 Uiso 1 1 calc R U . . .
B3 B 0.6786(3) 0.1106(3) 0.42277(17) 0.0514(8) Uani 1 1 d . . . . .
H3 H 0.6301 0.0275 0.4483 0.062 Uiso 1 1 calc R U . . .
B4 B 0.5802(4) 0.2500 0.4282(2) 0.0451(9) Uani 1 2 d S T P . .
B5 B 0.8530(5) 0.2500 0.3323(3) 0.0673(13) Uani 1 2 d S T P . .
H5 H 0.9203 0.2500 0.2862 0.081 Uiso 1 2 calc R U P . .
B6 B 0.7557(3) 0.1102(4) 0.33606(19) 0.0651(10) Uani 1 1 d . . . . .
H6 H 0.7618 0.0263 0.2984 0.078 Uiso 1 1 calc R U . . .
B7 B 0.5979(3) 0.1638(3) 0.34283(16) 0.0571(9) Uani 1 1 d . . . . .
H7 H 0.5204 0.1076 0.3188 0.069 Uiso 1 1 calc R U . . .
B8 B 0.7051(5) 0.2500 0.2864(2) 0.0665(13) Uani 1 2 d S T P . .
H8 H 0.6973 0.2500 0.2256 0.080 Uiso 1 2 calc R U P . .
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'
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
C18 N1 C19 108.2(2) . . ?
B9 C1 C2 0.0 7_565 7_565 ?
B9 C1 C2 63.0 7_565 . ?
C2 C1 C2 63.0(3) 7_565 . ?
B9 C1 B3 61.92(17) 7_565 7_565 ?
C2 C1 B3 61.92(17) 7_565 7_565 ?
C2 C1 B3 114.3(2) . 7_565 ?
B9 C1 B3 114.3(2) 7_565 . ?
C2 C1 B3 114.3(2) 7_565 . ?
C2 C1 B3 61.92(17) . . ?
B3 C1 B3 115.1(3) 7_565 . ?
B9 C1 B4 113.9(2) 7_565 . ?
C2 C1 B4 113.9(2) 7_565 . ?
C2 C1 B4 113.9(2) . . ?
B3 C1 B4 62.99(15) 7_565 . ?
B3 C1 B4 62.99(15) . . ?
C11 C2 C1 117.9(3) . . ?
C11 C2 B6 122.3(4) . . ?
C1 C2 B6 108.1(2) . . ?
C11 C2 B5 126.7(4) . . ?
C1 C2 B5 106.9(2) . . ?
B6 C2 B5 62.4(2) . . ?
C11 C2 B3 114.3(3) . . ?
C1 C2 B3 60.05(16) . . ?
B6 C2 B3 61.95(18) . . ?
B5 C2 B3 112.2(3) . . ?
C11 C2 B9 123.3(3) . 7_565 ?
C1 C2 B9 58.50(13) . 7_565 ?
B6 C2 B9 109.44(17) . 7_565 ?
B5 C2 B9 59.68(13) . 7_565 ?
B3 C2 B9 109.06(15) . 7_565 ?
C11 C2 C2 123.3(3) . 7_565 ?
C1 C2 C2 58.50(13) . 7_565 ?
B6 C2 C2 109.44(17) . 7_565 ?
B5 C2 C2 59.68(13) . 7_565 ?
B3 C2 C2 109.06(15) . 7_565 ?
B9 C2 C2 0.0 7_565 7_565 ?
C13 C12 C17 117.3(3) . . ?
C13 C12 B4 116.8(3) . . ?
C17 C12 B4 125.9(3) . . ?
C12 C13 C14 122.0(4) . . ?
C15 C14 C13 120.0(4) . . ?
C14 C15 C16 120.4(4) . . ?
C15 C16 C17 120.3(4) . . ?
C16 C17 C12 120.1(3) . . ?
C16 C17 C18 119.1(3) . . ?
C12 C17 C18 120.8(3) . . ?
C22 C18 N1 0.0 7_565 7_565 ?
C22 C18 N1 109.7 7_565 . ?
N1 C18 N1 109.7(3) 7_565 . ?
C22 C18 C17 124.95(17) 7_565 . ?
N1 C18 C17 124.95(17) 7_565 . ?
N1 C18 C17 124.95(17) . . ?
C20 C19 C19 120.5(2) . 7_565 ?
C20 C19 N1 132.5(3) . . ?
C19 C19 N1 106.94(16) 7_565 . ?
C21 C20 C19 117.7(4) . . ?
C20 C21 C21 121.8(3) . 7_565 ?
C1 B3 C2 58.03(18) . . ?
C1 B3 B7 104.3(2) . . ?
C2 B3 B7 106.2(2) . . ?
C1 B3 B6 103.8(2) . . ?
C2 B3 B6 58.45(18) . . ?
B7 B3 B6 60.42(18) . . ?
C1 B3 B4 58.84(18) . . ?
C2 B3 B4 107.3(2) . . ?
B7 B3 B4 60.49(19) . . ?
B6 B3 B4 109.0(2) . . ?
C12 B4 C1 124.5(3) . . ?
C12 B4 B3 121.51(16) . 7_565 ?
C1 B4 B3 58.16(15) . 7_565 ?
C12 B4 B3 121.52(16) . . ?
C1 B4 B3 58.17(15) . . ?
B3 B4 B3 107.2(3) 7_565 . ?
C12 B4 B7 124.4(2) . 7_565 ?
C1 B4 B7 102.9(2) . 7_565 ?
B3 B4 B7 59.40(16) 7_565 7_565 ?
B3 B4 B7 106.8(2) . 7_565 ?
C12 B4 B7 124.4(2) . . ?
C1 B4 B7 102.9(2) . . ?
B3 B4 B7 106.8(2) 7_565 . ?
B3 B4 B7 59.40(16) . . ?
B7 B4 B7 59.4(3) 7_565 . ?
C2 B5 B9 60.6 . 7_565 ?
C2 B5 C2 60.6(3) . 7_565 ?
B9 B5 C2 0.0 7_565 7_565 ?
C2 B5 B6 58.48(18) . . ?
B9 B5 B6 107.1(3) 7_565 . ?
C2 B5 B6 107.1(3) 7_565 . ?
C2 B5 B6 107.1(3) . 7_565 ?
B9 B5 B6 58.48(18) 7_565 7_565 ?
C2 B5 B6 58.48(18) 7_565 7_565 ?
B6 B5 B6 108.1(3) . 7_565 ?
C2 B5 B8 105.8(3) . . ?
B9 B5 B8 105.8(3) 7_565 . ?
C2 B5 B8 105.8(3) 7_565 . ?
B6 B5 B8 59.9(2) . . ?
B6 B5 B8 59.9(2) 7_565 . ?
C2 B6 B3 59.60(18) . . ?
C2 B6 B5 59.2(2) . . ?
B3 B6 B5 107.8(2) . . ?
C2 B6 B8 106.6(3) . . ?
B3 B6 B8 107.6(2) . . ?
B5 B6 B8 60.3(2) . . ?
C2 B6 B7 106.6(2) . . ?
B3 B6 B7 59.74(17) . . ?
B5 B6 B7 107.9(3) . . ?
B8 B6 B7 59.7(2) . . ?
B3 B7 B8 108.0(3) . . ?
B3 B7 B7 108.03(15) . 7_565 ?
B8 B7 B7 59.99(13) . 7_565 ?
B3 B7 B6 59.83(18) . . ?
B8 B7 B6 60.1(2) . . ?
B7 B7 B6 108.04(17) 7_565 . ?
B3 B7 B4 60.11(16) . . ?
B8 B7 B4 108.4(2) . . ?
B7 B7 B4 60.28(13) 7_565 . ?
B6 B7 B4 108.3(2) . . ?
B7 B8 B7 60.0(3) . 7_565 ?
B7 B8 B6 60.19(18) . . ?
B7 B8 B6 108.1(3) 7_565 . ?
B7 B8 B6 108.1(3) . 7_565 ?
B7 B8 B6 60.18(18) 7_565 7_565 ?
B6 B8 B6 107.9(3) . 7_565 ?
B7 B8 B5 107.9(3) . . ?
B7 B8 B5 107.9(3) 7_565 . ?
B6 B8 B5 59.77(19) . . ?
B6 B8 B5 59.77(19) 7_565 . ?
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
N1 C18 1.364(3) . ?
N1 C19 1.416(4) . ?
C1 B9 1.662(4) 7_565 ?
C1 C2 1.662(4) 7_565 ?
C1 C2 1.662(4) . ?
C1 B3 1.697(3) 7_565 ?
C1 B3 1.697(3) . ?
C1 B4 1.710(5) . ?
C2 C11 1.444(7) . ?
C2 B6 1.708(5) . ?
C2 B5 1.720(5) . ?
C2 B3 1.729(4) . ?
C2 B9 1.737(7) 7_565 ?
C2 C2 1.737(7) 7_565 ?
C12 C13 1.378(5) . ?
C12 C17 1.407(5) . ?
C12 B4 1.583(5) . ?
C13 C14 1.386(6) . ?
C14 C15 1.354(7) . ?
C15 C16 1.367(6) . ?
C16 C17 1.398(5) . ?
C17 C18 1.479(5) . ?
C18 C22 1.364(3) 7_565 ?
C18 N1 1.364(3) 7_565 ?
C19 C20 1.391(4) . ?
C19 C19 1.404(6) 7_565 ?
C20 C21 1.369(6) . ?
C21 C21 1.373(11) 7_565 ?
B3 B7 1.767(4) . ?
B3 B6 1.769(4) . ?
B3 B4 1.780(4) . ?
B4 B3 1.780(4) 7_565 ?
B4 B7 1.787(4) 7_565 ?
B4 B7 1.787(4) . ?
B5 B9 1.720(5) 7_565 ?
B5 C2 1.720(5) 7_565 ?
B5 B6 1.775(5) . ?
B5 B6 1.775(5) 7_565 ?
B5 B8 1.785(7) . ?
B6 B8 1.778(5) . ?
B6 B7 1.779(5) . ?
B7 B8 1.771(5) . ?
B7 B7 1.772(7) 7_565 ?
B8 B7 1.771(5) 7_565 ?
B8 B6 1.778(5) 7_565 ?
