#------------------------------------------------------------------------------
#$Date: 2019-11-17 08:06:17 +0200 (Sun, 17 Nov 2019) $
#$Revision: 228802 $
#$URL: file:///home/coder/svn-repositories/cod/cif/1/54/96/1549636.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_1549636
loop_
_publ_author_name
'Lyu, Hairong'
'Quan, Yangjian'
'Xie, Zuowei'
_publ_section_title
;
 Rhodium catalyzed cascade cyclization featuring B-H and C-H activation:
 one-step construction of carborane-fused N-polyheterocycles.
;
_journal_issue                   30
_journal_name_full               'Chemical science'
_journal_page_first              6390
_journal_page_last               6394
_journal_paper_doi               10.1039/c8sc01568f
_journal_volume                  9
_journal_year                    2018
_chemical_formula_sum            'C18 H22 B10 N'
_chemical_formula_weight         360.46
_space_group_crystal_system      orthorhombic
_space_group_IT_number           40
_space_group_name_Hall           'A 2 -2a'
_space_group_name_H-M_alt        'A m a 2'
_symmetry_space_group_name_Hall  'A 2 -2a'
_symmetry_space_group_name_H-M   'A m a 2'
_atom_sites_solution_hydrogens   mixed
_audit_creation_method           SHELXL-2014/6
_audit_update_record
;
2018-02-12 deposited with the CCDC.
2018-06-28 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   7.2240(3)
_cell_length_b                   24.5840(11)
_cell_length_c                   11.2382(5)
_cell_measurement_reflns_used    203
_cell_measurement_temperature    297(2)
_cell_measurement_theta_max      15
_cell_measurement_theta_min      15
_cell_volume                     1995.85(15)
_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      297(2)
_diffrn_measured_fraction_theta_full 0.991
_diffrn_measured_fraction_theta_max 0.991
_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  0.0382
_diffrn_reflns_av_unetI/netI     0.0161
_diffrn_reflns_Laue_measured_fraction_full 0.991
_diffrn_reflns_Laue_measured_fraction_max 0.991
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       29
_diffrn_reflns_limit_k_min       -29
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            25052
_diffrn_reflns_point_group_measured_fraction_full 0.993
_diffrn_reflns_point_group_measured_fraction_max 0.993
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         25.234
_diffrn_reflns_theta_min         3.315
_exptl_absorpt_coefficient_mu    0.061
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_correction_T_min  0.6689
_exptl_absorpt_correction_type   multi-scan
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.200
_exptl_crystal_description       block
_exptl_crystal_F_000             748
_exptl_crystal_size_max          0.500
_exptl_crystal_size_mid          0.400
_exptl_crystal_size_min          0.300
_refine_diff_density_max         0.169
_refine_diff_density_min         -0.174
_refine_diff_density_rms         0.034
_refine_ls_abs_structure_details
;
 Flack x determined using 793 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   1.7(7)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.054
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     174
_refine_ls_number_reflns         1961
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.054
_refine_ls_R_factor_all          0.0542
_refine_ls_R_factor_gt           0.0496
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.1017P)²+0.3867P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1390
_refine_ls_wR_factor_ref         0.1439
_reflns_Friedel_coverage         0.900
_reflns_Friedel_fraction_full    0.995
_reflns_Friedel_fraction_max     0.995
_reflns_number_gt                1786
_reflns_number_total             1961
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            c8sc01568f2.cif
_cod_data_source_block           LHR735
_cod_depositor_comments
'Adding full bibliography for 1549634--1549636.cif.'
_cod_database_code               1549636
_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   0.970
_shelx_estimated_absorpt_t_max   0.982
_shelxl_version_number           2014/6
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, z'
'x+1/2, -y, z'
'-x+1/2, y, z'
'x, y+1/2, z+1/2'
'-x, -y+1/2, z+1/2'
'x+1/2, -y+1/2, z+1/2'
'-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
N1 N 0.7500 0.04037(13) 0.6453(3) 0.0449(8) Uani 1 2 d S T P
C1 C 0.7500 0.13260(15) 0.5638(4) 0.0463(9) Uani 1 2 d S T P
C2 C 0.6322(7) 0.12933(15) 0.4361(3) 0.0740(11) Uani 0.5 1 d . . P
B6 B 0.6322(7) 0.12933(15) 0.4361(3) 0.0740(11) Uani 0.5 1 d . . P
C11 C 0.5401(14) 0.0807(3) 0.4089(8) 0.090(3) Uani 0.5 1 d . . P
H11A H 0.4784 0.0843 0.3337 0.135 Uiso 0.5 1 calc R U P
H11B H 0.6282 0.0515 0.4047 0.135 Uiso 0.5 1 calc R U P
H11C H 0.4506 0.0730 0.4698 0.135 Uiso 0.5 1 calc R U P
C12 C 0.7500 0.09326(14) 0.6639(4) 0.0403(9) Uani 1 2 d S T P
C13 C 0.7500 0.11907(14) 0.7737(4) 0.0434(9) Uani 1 2 d S T P
C14 C 0.7500 0.18127(16) 0.7671(5) 0.0605(11) Uani 1 2 d S T P
H14A H 0.8592 0.1962 0.8053 0.073 Uiso 0.5 1 calc R U P
H14B H 0.6408 0.1962 0.8053 0.073 Uiso 0.5 1 calc R U P
C15 C 0.7500 0.08783(16) 0.8759(4) 0.0435(9) Uani 1 2 d S T P
C16 C 0.7500 0.1174(2) 0.9941(5) 0.0715(14) Uani 1 2 d S T P
C17 C 0.7500 0.03010(16) 0.8627(4) 0.0424(9) Uani 1 2 d S T P
C18 C 0.7500 -0.00934(18) 0.9604(4) 0.0538(10) Uani 1 2 d S T P
C19 C 0.7500 0.0034(3) 1.0802(5) 0.131(4) Uani 1 2 d S T P
H19A H 0.7500 0.0398 1.1028 0.157 Uiso 1 2 calc R U P
C20 C 0.7500 -0.0357(3) 1.1666(6) 0.138(4) Uani 1 2 d S T P
H20A H 0.7500 -0.0250 1.2460 0.166 Uiso 1 2 calc R U P
C21 C 0.7500 -0.0896(3) 1.1408(6) 0.093(2) Uani 1 2 d S T P
H21A H 0.7500 -0.1155 1.2012 0.112 Uiso 1 2 calc R U P
C22 C 0.7500 -0.10469(19) 1.0258(5) 0.0687(13) Uani 1 2 d S T P
H22A H 0.7500 -0.1415 1.0064 0.082 Uiso 1 2 calc R U P
C23 C 0.7500 -0.06530(16) 0.9337(4) 0.0520(11) Uani 1 2 d S T P
C24 C 0.7500 -0.08378(16) 0.8134(5) 0.0574(11) Uani 1 2 d S T P
H24A H 0.7500 -0.1209 0.7974 0.069 Uiso 1 2 calc R U P
C25 C 0.7500 -0.04822(16) 0.7235(4) 0.0526(10) Uani 1 2 d S T P
H25A H 0.7500 -0.0609 0.6456 0.063 Uiso 1 2 calc R U P
C26 C 0.7500 0.00902(14) 0.7452(3) 0.0414(9) Uani 1 2 d S T P
B3 B 0.5514(5) 0.16936(15) 0.5523(4) 0.0601(9) Uani 1 1 d . . .
H3 H 0.4312 0.1697 0.6124 0.072 Uiso 1 1 calc R U .
B4 B 0.7500 0.19466(18) 0.6289(5) 0.0526(11) Uani 1 2 d S T P
B5 B 0.5528(7) 0.19451(18) 0.4068(4) 0.0770(13) Uani 1 1 d . . .
H5 H 0.4342 0.2137 0.3620 0.092 Uiso 1 1 calc R U .
B7 B 0.6260(6) 0.23681(15) 0.5267(4) 0.0678(10) Uani 1 1 d . . .
H7 H 0.5454 0.2722 0.5566 0.081 Uiso 1 1 calc R U .
B8 B 0.7500 0.1676(3) 0.3335(6) 0.0835(19) Uani 1 2 d S T P
H8 H 0.7500 0.1733 0.2365 0.100 Uiso 1 2 calc R U P
B9 B 0.7500 0.2367(3) 0.3911(7) 0.0770(18) Uani 1 2 d S T P
H9 H 0.7500 0.2726 0.3326 0.092 Uiso 1 2 calc R U P
H16A H 0.806(5) 0.1584(17) 0.974(4) 0.023(12) Uiso 0.5 1 d . . P
H16B H 0.852(6) 0.1132(17) 1.043(4) 0.104(15) Uiso 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'
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
C12 N1 C26 115.4(3) . .
C12 C1 B6 128.3(3) . 4_655
C12 C1 C2 128.3(3) . 4_655
B6 C1 C2 0.0 4_655 4_655
C12 C1 C2 128.3(3) . .
B6 C1 C2 61.2 4_655 .
C2 C1 C2 61.2(4) 4_655 .
C12 C1 B4 105.1(3) . .
B6 C1 B4 114.5(3) 4_655 .
C2 C1 B4 114.5(3) 4_655 .
C2 C1 B4 114.5(3) . .
C12 C1 B3 113.8(2) . .
B6 C1 B3 113.0(3) 4_655 .
C2 C1 B3 113.0(3) 4_655 .
C2 C1 B3 62.0(2) . .
B4 C1 B3 63.49(19) . .
C12 C1 B3 113.8(2) . 4_655
B6 C1 B3 62.0(2) 4_655 4_655
C2 C1 B3 62.0(2) 4_655 4_655
C2 C1 B3 113.0(3) . 4_655
B4 C1 B3 63.49(19) . 4_655
B3 C1 B3 115.1(3) . 4_655
C11 C2 C1 118.0(4) . .
C11 C2 B6 118.3(5) . 4_655
C1 C2 B6 59.38(18) . 4_655
C11 C2 C2 118.3(5) . 4_655
C1 C2 C2 59.38(18) . 4_655
B6 C2 C2 0.0 4_655 4_655
C11 C2 B8 123.9(5) . .
C1 C2 B8 107.4(3) . .
B6 C2 B8 60.21(18) 4_655 .
C2 C2 B8 60.21(18) 4_655 .
C11 C2 B5 126.2(5) . .
C1 C2 B5 106.7(3) . .
B6 C2 B5 109.3(2) 4_655 .
C2 C2 B5 109.3(2) 4_655 .
B8 C2 B5 61.9(3) . .
C11 C2 B3 119.2(6) . .
C1 C2 B3 59.83(19) . .
B6 C2 B3 109.63(18) 4_655 .
C2 C2 B3 109.63(18) 4_655 .
B8 C2 B3 111.2(4) . .
B5 C2 B3 60.5(2) . .
N1 C12 C13 126.3(3) . .
N1 C12 C1 121.6(3) . .
C13 C12 C1 112.1(3) . .
C15 C13 C12 119.0(3) . .
C15 C13 C14 126.5(4) . .
C12 C13 C14 114.4(4) . .
C13 C14 B4 104.8(4) . .
C13 C15 C17 117.8(4) . .
C13 C15 C16 117.6(4) . .
C17 C15 C16 124.7(4) . .
C26 C17 C15 117.4(3) . .
C26 C17 C18 117.1(4) . .
C15 C17 C18 125.4(4) . .
C19 C18 C23 115.4(5) . .
C19 C18 C17 125.5(5) . .
C23 C18 C17 119.1(4) . .
C20 C19 C18 122.2(6) . .
C21 C20 C19 122.4(7) . .
C22 C21 C20 118.4(5) . .
C21 C22 C23 120.9(5) . .
C18 C23 C22 120.8(4) . .
C18 C23 C24 120.9(4) . .
C22 C23 C24 118.3(4) . .
C25 C24 C23 120.5(4) . .
C24 C25 C26 121.1(4) . .
N1 C26 C17 124.1(3) . .
N1 C26 C25 114.7(3) . .
C17 C26 C25 121.2(4) . .
C1 B3 C2 58.2(2) . .
C1 B3 B5 104.7(3) . .
C2 B3 B5 59.7(2) . .
C1 B3 B7 104.7(3) . .
C2 B3 B7 107.9(3) . .
B5 B3 B7 60.9(2) . .
C1 B3 B4 58.0(2) . .
C2 B3 B4 106.9(3) . .
B5 B3 B4 108.9(3) . .
B7 B3 B4 60.4(2) . .
C14 B4 C1 103.6(3) . .
C14 B4 B3 113.5(2) . .
C1 B4 B3 58.49(18) . .
C14 B4 B3 113.5(2) . 4_655
C1 B4 B3 58.49(18) . 4_655
B3 B4 B3 107.0(4) . 4_655
C14 B4 B7 138.5(3) . .
C1 B4 B7 104.2(3) . .
B3 B4 B7 59.3(2) . .
B3 B4 B7 107.2(3) 4_655 .
C14 B4 B7 138.5(3) . 4_655
C1 B4 B7 104.2(3) . 4_655
B3 B4 B7 107.2(3) . 4_655
B3 B4 B7 59.3(2) 4_655 4_655
B7 B4 B7 60.1(3) . 4_655
C2 B5 B3 59.8(2) . .
C2 B5 B9 107.1(3) . .
B3 B5 B9 107.8(4) . .
C2 B5 B8 58.5(3) . .
B3 B5 B8 107.9(3) . .
B9 B5 B8 61.7(3) . .
C2 B5 B7 107.3(3) . .
B3 B5 B7 60.1(2) . .
B9 B5 B7 59.7(3) . .
B8 B5 B7 109.3(3) . .
B3 B7 B9 107.1(3) . .
B3 B7 B5 59.0(2) . .
B9 B7 B5 59.9(3) . .
B3 B7 B4 60.28(19) . .
B9 B7 B4 107.4(3) . .
B5 B7 B4 107.2(3) . .
B3 B7 B7 107.76(17) . 4_655
B9 B7 B7 59.56(19) . 4_655
B5 B7 B7 107.3(2) . 4_655
B4 B7 B7 59.93(16) . 4_655
C2 B8 B6 59.6 . 4_655
C2 B8 C2 59.6(4) . 4_655
B6 B8 C2 0.0 4_655 4_655
C2 B8 B5 107.0(4) . 4_655
B6 B8 B5 59.6(2) 4_655 4_655
C2 B8 B5 59.6(2) 4_655 4_655
C2 B8 B5 59.6(2) . .
B6 B8 B5 107.0(4) 4_655 .
C2 B8 B5 107.0(4) 4_655 .
B5 B8 B5 106.9(5) 4_655 .
C2 B8 B9 105.9(4) . .
B6 B8 B9 105.9(4) 4_655 .
C2 B8 B9 105.9(4) 4_655 .
B5 B8 B9 59.1(3) 4_655 .
B5 B8 B9 59.1(3) . .
B7 B9 B7 60.9(4) . 4_655
B7 B9 B5 60.5(3) . .
B7 B9 B5 108.8(4) 4_655 .
B7 B9 B5 108.8(4) . 4_655
B7 B9 B5 60.5(3) 4_655 4_655
B5 B9 B5 107.1(4) . 4_655
B7 B9 B8 107.9(3) . .
B7 B9 B8 107.9(3) 4_655 .
B5 B9 B8 59.2(3) . .
B5 B9 B8 59.2(3) 4_655 .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
N1 C12 1.317(5) .
N1 C26 1.361(5) .
C1 C12 1.483(5) .
C1 B6 1.671(5) 4_655
C1 C2 1.671(5) 4_655
C1 C2 1.671(5) .
C1 B4 1.692(6) .
C1 B3 1.700(4) .
C1 B3 1.700(4) 4_655
C2 C11 1.402(9) .
C2 B6 1.703(9) 4_655
C2 C2 1.703(9) 4_655
C2 B8 1.713(7) .
C2 B5 1.733(6) .
C2 B3 1.736(6) .
C12 C13 1.388(5) .
C13 C15 1.382(6) .
C13 C14 1.531(5) .
C14 B4 1.587(7) .
C15 C17 1.427(5) .
C15 C16 1.514(6) .
C17 C26 1.418(5) .
C17 C18 1.465(6) .
C18 C19 1.383(8) .
C18 C23 1.408(6) .
C19 C20 1.367(8) .
C20 C21 1.355(10) .
C21 C22 1.345(9) .
C22 C23 1.417(6) .
C23 C24 1.426(7) .
C24 C25 1.335(7) .
C25 C26 1.428(5) .
B3 B5 1.748(6) .
B3 B7 1.767(5) .
B3 B4 1.785(5) .
B4 B3 1.785(5) 4_655
B4 B7 1.787(6) .
B4 B7 1.787(6) 4_655
B5 B9 1.772(6) .
B5 B8 1.774(7) .
B5 B7 1.782(7) .
B7 B9 1.768(8) .
B7 B7 1.791(8) 4_655
B8 B6 1.714(7) 4_655
B8 C2 1.714(7) 4_655
B8 B5 1.774(7) 4_655
B8 B9 1.819(10) .
B9 B7 1.768(8) 4_655
B9 B5 1.772(6) 4_655
