#------------------------------------------------------------------------------
#$Date: 2020-07-06 04:44:48 +0300 (Mon, 06 Jul 2020) $
#$Revision: 253776 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/12/65/7126541.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_7126541
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            'C13 H20 B10 N2'
_chemical_formula_weight         312.41
_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
_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                   11.3782(12)
_cell_length_b                   11.4876(11)
_cell_length_c                   13.5646(15)
_cell_measurement_reflns_used    349
_cell_measurement_temperature    298(2)
_cell_measurement_theta_max      15
_cell_measurement_theta_min      15
_cell_volume                     1773.0(3)
_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      298(2)
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_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  0.1414
_diffrn_reflns_av_unetI/netI     0.0491
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            67985
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 1.000
_diffrn_reflns_theta_full        25.233
_diffrn_reflns_theta_max         25.233
_diffrn_reflns_theta_min         2.323
_exptl_absorpt_coefficient_mu    0.060
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_correction_T_min  0.5181
_exptl_absorpt_correction_type   multi-scan
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.170
_exptl_crystal_description       block
_exptl_crystal_F_000             648
_exptl_crystal_size_max          0.400
_exptl_crystal_size_mid          0.300
_exptl_crystal_size_min          0.200
_refine_diff_density_max         0.558
_refine_diff_density_min         -0.265
_refine_diff_density_rms         0.058
_refine_ls_abs_structure_details
;
 Flack x determined using 774 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -5.4(10)
_refine_ls_extinction_coef       0.030(9)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2018/3 (Sheldrick 2018)'
_refine_ls_goodness_of_fit_ref   1.037
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     227
_refine_ls_number_reflns         3218
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.037
_refine_ls_R_factor_all          0.1113
_refine_ls_R_factor_gt           0.0826
_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)+(0.1321P)²+0.8621P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2131
_refine_ls_wR_factor_ref         0.2336
_reflns_Friedel_coverage         0.741
_reflns_Friedel_fraction_full    1.000
_reflns_Friedel_fraction_max     1.000
_reflns_number_gt                2380
_reflns_number_total             3218
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d0cc02531c2.cif
_cod_data_source_block           3aq
_cod_depositor_comments
'Adding full bibliography for 7126537--7126543.cif.'
_cod_database_code               7126541
_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   0.976
_shelx_estimated_absorpt_t_max   0.988
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'
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 0.4685(4) 0.9142(4) 0.1951(3) 0.0532(12) Uani 1 1 d . . . . .
N2 N 0.5764(4) 0.7379(4) 0.2036(3) 0.0564(12) Uani 1 1 d . . . . .
C1 C 0.2377(7) 0.9123(7) 0.3037(6) 0.087(2) Uani 1 1 d . . . . .
H1 H 0.300077 0.967917 0.263466 0.104 Uiso 1 1 calc R U . . .
C2 C 0.2265(9) 0.9188(8) 0.4193(6) 0.100(3) Uani 1 1 d . . . . .
C11 C 0.3097(10) 1.0037(11) 0.4727(9) 0.166(6) Uani 1 1 d . . . . .
H11A H 0.370473 0.960558 0.505437 0.249 Uiso 1 1 calc R U . . .
H11B H 0.344438 1.055659 0.425480 0.249 Uiso 1 1 calc R U . . .
H11C H 0.266074 1.047864 0.520307 0.249 Uiso 1 1 calc R U . . .
C12 C 0.2714(4) 0.7352(4) 0.1528(3) 0.0411(11) Uani 1 1 d . . . . .
C13 C 0.1931(5) 0.6724(5) 0.0902(4) 0.0545(15) Uani 1 1 d . . . . .
H13A H 0.114391 0.666028 0.107937 0.065 Uiso 1 1 calc R U . . .
C14 C 0.2307(6) 0.6213(5) 0.0046(4) 0.0656(17) Uani 1 1 d . . . . .
H14A H 0.176647 0.583024 -0.035357 0.079 Uiso 1 1 calc R U . . .
C15 C 0.3459(6) 0.6253(6) -0.0232(5) 0.0710(18) Uani 1 1 d . . . . .
H15A H 0.370849 0.588945 -0.080774 0.085 Uiso 1 1 calc R U . . .
C16 C 0.4241(5) 0.6843(5) 0.0355(4) 0.0565(15) Uani 1 1 d . . . . .
H16A H 0.502723 0.687246 0.017017 0.068 Uiso 1 1 calc R U . . .
C17 C 0.3889(4) 0.7402(4) 0.1225(3) 0.0399(11) Uani 1 1 d . . . . .
C18 C 0.4835(4) 0.8010(4) 0.1791(3) 0.0402(12) Uani 1 1 d . . . . .
C19 C 0.5561(5) 0.9669(5) 0.2443(5) 0.0637(17) Uani 1 1 d . . . . .
H19A H 0.549820 1.046070 0.257450 0.076 Uiso 1 1 calc R U . . .
C20 C 0.6536(6) 0.9092(7) 0.2755(5) 0.0695(18) Uani 1 1 d . . . . .
H20A H 0.712619 0.946643 0.310783 0.083 Uiso 1 1 calc R U . . .
C21 C 0.6605(5) 0.7947(6) 0.2529(5) 0.0648(17) Uani 1 1 d . . . . .
H21A H 0.726861 0.753515 0.272590 0.078 Uiso 1 1 calc R U . . .
B3 B 0.1232(11) 0.9733(12) 0.3624(11) 0.131(5) Uani 1 1 d . . . . .
H3 H 0.104381 1.067172 0.364541 0.157 Uiso 1 1 calc R U . . .
B4 B 0.1081(9) 0.8910(10) 0.2572(8) 0.109(4) Uani 1 1 d . . . . .
H4 H 0.077657 0.930626 0.187969 0.131 Uiso 1 1 calc R U . . .
B5 B 0.2151(5) 0.7784(5) 0.2520(4) 0.0440(13) Uani 1 1 d . . . . .
B6 B 0.2943(7) 0.8051(9) 0.3610(5) 0.080(3) Uani 1 1 d . . . . .
H6 H 0.389263 0.787251 0.363037 0.096 Uiso 1 1 calc R U . . .
B7 B 0.0936(8) 0.8790(11) 0.4653(8) 0.102(3) Uani 1 1 d . . . . .
H7 H 0.051386 0.904595 0.534930 0.122 Uiso 1 1 calc R U . . .
B8 B 0.0160(8) 0.8726(15) 0.3567(10) 0.141(6) Uani 1 1 d . . . . .
H8 H -0.076722 0.899468 0.354209 0.169 Uiso 1 1 calc R U . . .
B9 B 0.0683(8) 0.7540(13) 0.2896(9) 0.136(6) Uani 1 1 d . . . . .
H9 H 0.007383 0.702715 0.243981 0.163 Uiso 1 1 calc R U . . .
B10 B 0.1932(11) 0.6937(8) 0.3585(8) 0.110(4) Uani 1 1 d . . . . .
H10 H 0.217264 0.600918 0.358718 0.132 Uiso 1 1 calc R U . . .
B11 B 0.2098(9) 0.7865(11) 0.4642(7) 0.102(3) Uani 1 1 d . . . . .
H11 H 0.250038 0.758462 0.534048 0.122 Uiso 1 1 calc R U . . .
B12 B 0.0706(13) 0.7408(11) 0.4234(10) 0.156(7) Uani 1 1 d . . . . .
H12 H 0.016665 0.676849 0.463458 0.187 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'
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 115.2(5) . . ?
C18 N2 C21 115.5(5) . . ?
C2 C1 B6 65.4(6) . . ?
C2 C1 B4 108.7(7) . . ?
B6 C1 B4 116.2(7) . . ?
C2 C1 B3 56.3(7) . . ?
B6 C1 B3 113.9(8) . . ?
B4 C1 B3 62.8(6) . . ?
C2 C1 B5 116.0(6) . . ?
B6 C1 B5 64.2(4) . . ?
B4 C1 B5 64.4(5) . . ?
B3 C1 B5 117.0(6) . . ?
B3 C2 C11 116.6(9) . . ?
B3 C2 C1 65.3(7) . . ?
C11 C2 C1 116.6(8) . . ?
B3 C2 B11 118.2(9) . . ?
C11 C2 B11 118.7(10) . . ?
C1 C2 B11 109.5(6) . . ?
B3 C2 B7 67.3(8) . . ?
C11 C2 B7 123.0(7) . . ?
C1 C2 B7 115.1(7) . . ?
B11 C2 B7 60.9(6) . . ?
B3 C2 B6 115.0(7) . . ?
C11 C2 B6 115.1(8) . . ?
C1 C2 B6 57.8(5) . . ?
B11 C2 B6 61.3(5) . . ?
B7 C2 B6 111.5(7) . . ?
C17 C12 C13 116.2(5) . . ?
C17 C12 B5 128.9(4) . . ?
C13 C12 B5 114.5(4) . . ?
C14 C13 C12 121.8(5) . . ?
C15 C14 C13 121.3(5) . . ?
C14 C15 C16 118.6(6) . . ?
C15 C16 C17 122.0(5) . . ?
C12 C17 C16 120.1(4) . . ?
C12 C17 C18 123.7(4) . . ?
C16 C17 C18 116.2(4) . . ?
N2 C18 N1 126.7(5) . . ?
N2 C18 C17 116.6(4) . . ?
N1 C18 C17 116.6(5) . . ?
N1 C19 C20 122.7(5) . . ?
C21 C20 C19 116.8(6) . . ?
N2 C21 C20 123.1(6) . . ?
C2 B3 C1 58.4(6) . . ?
C2 B3 B8 107.3(11) . . ?
C1 B3 B8 104.7(7) . . ?
C2 B3 B4 105.6(8) . . ?
C1 B3 B4 57.0(5) . . ?
B8 B3 B4 60.8(7) . . ?
C2 B3 B7 60.6(8) . . ?
C1 B3 B7 105.2(9) . . ?
B8 B3 B7 59.1(8) . . ?
B4 B3 B7 107.1(9) . . ?
C1 B4 B9 106.4(8) . . ?
C1 B4 B3 60.3(6) . . ?
B9 B4 B3 108.8(9) . . ?
C1 B4 B8 105.5(7) . . ?
B9 B4 B8 61.3(7) . . ?
B3 B4 B8 58.5(7) . . ?
C1 B4 B5 60.2(4) . . ?
B9 B4 B5 61.2(5) . . ?
B3 B4 B5 111.4(8) . . ?
B8 B4 B5 111.0(8) . . ?
C12 B5 C1 125.0(5) . . ?
C12 B5 B6 124.5(5) . . ?
C1 B5 B6 54.6(5) . . ?
C12 B5 B10 125.9(5) . . ?
C1 B5 B10 100.5(5) . . ?
B6 B5 B10 58.6(5) . . ?
C12 B5 B9 125.6(5) . . ?
C1 B5 B9 99.6(5) . . ?
B6 B5 B9 105.6(6) . . ?
B10 B5 B9 62.7(7) . . ?
C12 B5 B4 122.9(5) . . ?
C1 B5 B4 55.4(5) . . ?
B6 B5 B4 101.0(5) . . ?
B10 B5 B4 105.8(6) . . ?
B9 B5 B4 57.1(7) . . ?
C1 B6 C2 56.8(5) . . ?
C1 B6 B11 105.6(7) . . ?
C2 B6 B11 57.6(6) . . ?
C1 B6 B10 107.2(6) . . ?
C2 B6 B10 106.0(6) . . ?
B11 B6 B10 63.1(6) . . ?
C1 B6 B5 61.1(4) . . ?
C2 B6 B5 106.9(6) . . ?
B11 B6 B5 112.2(6) . . ?
B10 B6 B5 60.8(5) . . ?
B11 B7 C2 58.1(6) . . ?
B11 B7 B12 62.2(8) . . ?
C2 B7 B12 105.4(7) . . ?
B11 B7 B8 111.5(7) . . ?
C2 B7 B8 98.9(7) . . ?
B12 B7 B8 66.2(9) . . ?
B11 B7 B3 103.0(7) . . ?
C2 B7 B3 52.1(6) . . ?
B12 B7 B3 109.3(8) . . ?
B8 B7 B3 57.1(8) . . ?
B3 B8 B7 63.8(8) . . ?
B3 B8 B4 60.7(8) . . ?
B7 B8 B4 110.7(7) . . ?
B3 B8 B9 108.3(7) . . ?
B7 B8 B9 107.8(9) . . ?
B4 B8 B9 58.6(6) . . ?
B3 B8 B12 107.1(9) . . ?
B7 B8 B12 56.6(7) . . ?
B4 B8 B12 106.1(7) . . ?
B9 B8 B12 60.4(8) . . ?
B4 B9 B8 60.1(8) . . ?
B4 B9 B5 61.7(5) . . ?
B8 B9 B5 110.4(7) . . ?
B4 B9 B12 109.4(7) . . ?
B8 B9 B12 63.2(7) . . ?
B5 B9 B12 106.7(8) . . ?
B4 B9 B10 106.0(6) . . ?
B8 B9 B10 107.0(7) . . ?
B5 B9 B10 58.4(5) . . ?
B12 B9 B10 56.7(7) . . ?
B6 B10 B12 107.2(7) . . ?
B6 B10 B5 60.7(4) . . ?
B12 B10 B5 111.0(8) . . ?
B6 B10 B11 58.2(6) . . ?
B12 B10 B11 59.7(6) . . ?
B5 B10 B11 108.2(6) . . ?
B6 B10 B9 104.3(6) . . ?
B12 B10 B9 61.2(8) . . ?
B5 B10 B9 58.9(5) . . ?
B11 B10 B9 105.3(6) . . ?
C2 B11 B7 61.0(7) . . ?
C2 B11 B6 61.1(6) . . ?
B7 B11 B6 111.5(8) . . ?
C2 B11 B12 105.2(9) . . ?
B7 B11 B12 59.2(6) . . ?
B6 B11 B12 106.6(7) . . ?
C2 B11 B10 105.3(6) . . ?
B7 B11 B10 107.2(8) . . ?
B6 B11 B10 58.7(5) . . ?
B12 B11 B10 58.4(6) . . ?
B7 B12 B10 109.6(8) . . ?
B7 B12 B11 58.6(7) . . ?
B10 B12 B11 61.9(7) . . ?
B7 B12 B9 104.8(10) . . ?
B10 B12 B9 62.1(6) . . ?
B11 B12 B9 107.6(6) . . ?
B7 B12 B8 57.2(7) . . ?
B10 B12 B8 105.9(8) . . ?
B11 B12 B8 102.1(8) . . ?
B9 B12 B8 56.3(8) . . ?
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 1.329(6) . ?
N1 C19 1.344(7) . ?
N2 C18 1.323(6) . ?
N2 C21 1.338(7) . ?
C1 C2 1.575(11) . ?
C1 B6 1.592(13) . ?
C1 B4 1.622(13) . ?
C1 B3 1.680(12) . ?
C1 B5 1.710(9) . ?
C2 B3 1.539(17) . ?
C2 C11 1.540(12) . ?
C2 B11 1.648(15) . ?
C2 B7 1.699(13) . ?
C2 B6 1.711(12) . ?
C12 C17 1.400(7) . ?
C12 C13 1.427(7) . ?
C12 B5 1.570(8) . ?
C13 C14 1.370(8) . ?
C14 C15 1.364(9) . ?
C15 C16 1.373(8) . ?
C16 C17 1.402(7) . ?
C17 C18 1.495(7) . ?
C19 C20 1.360(9) . ?
C20 C21 1.353(9) . ?
B3 B8 1.682(19) . ?
B3 B4 1.720(16) . ?
B3 B7 1.80(2) . ?
B4 B9 1.695(19) . ?
B4 B8 1.721(17) . ?
B4 B5 1.778(10) . ?
B5 B6 1.758(9) . ?
B5 B10 1.760(10) . ?
B5 B9 1.769(9) . ?
B6 B11 1.713(11) . ?
B6 B10 1.722(14) . ?
B7 B11 1.696(15) . ?
B7 B12 1.707(15) . ?
B7 B8 1.719(16) . ?
B8 B9 1.743(16) . ?
B8 B12 1.87(2) . ?
B9 B12 1.82(2) . ?
B9 B10 1.837(18) . ?
B10 B12 1.736(14) . ?
B10 B11 1.797(16) . ?
B11 B12 1.759(18) . ?
