#------------------------------------------------------------------------------
#$Date: 2019-11-17 07:30:56 +0200 (Sun, 17 Nov 2019) $
#$Revision: 228678 $
#$URL: file:///home/coder/svn-repositories/cod/cif/1/54/86/1548699.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_1548699
loop_
_publ_author_name
'Chan, Tek Long'
'Xie, Zuowei'
_publ_section_title
;
 Synthesis, structure and aromaticity of carborane-fused carbo- and
 heterocycles.
;
_journal_issue                   8
_journal_name_full               'Chemical science'
_journal_page_first              2284
_journal_page_last               2289
_journal_paper_doi               10.1039/c7sc04722c
_journal_volume                  9
_journal_year                    2018
_chemical_formula_sum            'C6 H17 B10 N'
_chemical_formula_weight         211.30
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2yn'
_space_group_name_H-M_alt        'P 1 21/n 1'
_symmetry_space_group_name_Hall  '-P 2yn'
_symmetry_space_group_name_H-M   'P 1 21/n 1'
_atom_sites_solution_hydrogens   geom
_audit_creation_method           SHELXL-2014/6
_audit_update_record
;
2017-10-31 deposited with the CCDC.
2018-01-16 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 108.729(6)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   11.9424(13)
_cell_length_b                   8.5259(8)
_cell_length_c                   13.3359(12)
_cell_measurement_reflns_used    63
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      15
_cell_measurement_theta_min      15
_cell_volume                     1286.0(2)
_computing_cell_refinement       'BRUKER KAPPA APEXII DUO DIFFRACTOMETER'
_computing_data_collection       'BRUKER KAPPA APEXII DUO DIFFRACTOMETER'
_computing_data_reduction        'BRUKER KAPPA APEXII DUO 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 0.996
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measurement_device_type  'BRUKER KAPPA APEXII DUO DIFFRACTOMETER'
_diffrn_measurement_method       'PHI & OMEGA SCAN'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0488
_diffrn_reflns_av_unetI/netI     0.0490
_diffrn_reflns_Laue_measured_fraction_full 0.996
_diffrn_reflns_Laue_measured_fraction_max 0.996
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_number            8033
_diffrn_reflns_point_group_measured_fraction_full 0.996
_diffrn_reflns_point_group_measured_fraction_max 0.996
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         25.236
_diffrn_reflns_theta_min         1.994
_exptl_absorpt_coefficient_mu    0.051
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_correction_T_min  0.6834
_exptl_absorpt_correction_type   multi-scan
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.091
_exptl_crystal_description       block
_exptl_crystal_F_000             440
_exptl_crystal_size_max          0.400
_exptl_crystal_size_mid          0.300
_exptl_crystal_size_min          0.200
_refine_diff_density_max         0.283
_refine_diff_density_min         -0.227
_refine_diff_density_rms         0.044
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.065
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     154
_refine_ls_number_reflns         2315
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.065
_refine_ls_R_factor_all          0.1208
_refine_ls_R_factor_gt           0.0768
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.1241P)²+0.6681P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2184
_refine_ls_wR_factor_ref         0.2534
_reflns_Friedel_coverage         0.000
_reflns_number_gt                1450
_reflns_number_total             2315
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            c7sc04722c2.cif
_cod_data_source_block           17
_cod_depositor_comments
'Adding full bibliography for 1548696--1548701.cif.'
_cod_database_code               1548699
_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   0.980
_shelx_estimated_absorpt_t_max   0.990
_shelxl_version_number           2014/6
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -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
N3 N 0.1106(3) 1.0085(3) 0.3299(2) 0.0700(9) Uani 1 1 d . .
C1 C -0.0312(3) 0.8520(3) 0.1995(2) 0.0457(8) Uani 1 1 d . .
C2 C 0.0683(3) 0.8508(3) 0.3149(2) 0.0481(8) Uani 1 1 d . .
C4 C 0.0479(3) 1.0950(4) 0.2425(3) 0.0664(10) Uani 1 1 d . .
H4A H 0.0592 1.2023 0.2375 0.080 Uiso 1 1 calc R U
C5 C -0.0308(3) 1.0136(3) 0.1653(2) 0.0542(9) Uani 1 1 d . .
C11 C -0.1120(3) 1.0739(4) 0.0662(3) 0.0690(10) Uani 1 1 d . .
H11A H -0.1579 0.9890 0.0262 0.103 Uiso 1 1 calc R U
H11B H -0.1638 1.1498 0.0813 0.103 Uiso 1 1 calc R U
H11C H -0.0677 1.1225 0.0260 0.103 Uiso 1 1 calc R U
C12 C 0.1832(4) 1.0692(5) 0.4315(3) 0.0789(12) Uani 1 1 d . .
H12A H 0.2168 0.9834 0.4781 0.118 Uiso 1 1 calc R U
H12B H 0.2455 1.1325 0.4220 0.118 Uiso 1 1 calc R U
H12C H 0.1354 1.1319 0.4617 0.118 Uiso 1 1 calc R U
B3 B -0.0793(4) 0.8319(5) 0.3094(3) 0.0621(11) Uani 1 1 d . .
H3 H -0.1309 0.9190 0.3367 0.075 Uiso 1 1 calc R U
B4 B -0.1430(3) 0.7232(5) 0.1943(3) 0.0612(10) Uani 1 1 d . .
H4 H -0.2360 0.7409 0.1463 0.073 Uiso 1 1 calc R U
B5 B -0.0326(3) 0.6792(4) 0.1344(3) 0.0548(10) Uani 1 1 d . .
H5 H -0.0551 0.6689 0.0480 0.066 Uiso 1 1 calc R U
B6 B 0.1035(3) 0.7595(4) 0.2121(3) 0.0508(9) Uani 1 1 d . .
H6 H 0.1699 0.7996 0.1767 0.061 Uiso 1 1 calc R U
B7 B 0.0342(4) 0.7232(5) 0.3990(3) 0.0650(11) Uani 1 1 d . .
H7 H 0.0571 0.7414 0.4849 0.078 Uiso 1 1 calc R U
B8 B -0.0994(4) 0.6314(5) 0.3211(4) 0.0738(13) Uani 1 1 d . .
H8 H -0.1641 0.5847 0.3562 0.089 Uiso 1 1 calc R U
B9 B -0.0731(4) 0.5377(5) 0.2132(3) 0.0649(11) Uani 1 1 d . .
H9 H -0.1219 0.4314 0.1775 0.078 Uiso 1 1 calc R U
B10 B 0.0775(4) 0.5615(4) 0.2255(3) 0.0610(10) Uani 1 1 d . .
H10 H 0.1265 0.4700 0.1989 0.073 Uiso 1 1 calc R U
B11 B 0.1447(3) 0.6793(4) 0.3397(3) 0.0601(11) Uani 1 1 d . .
H11 H 0.2384 0.6690 0.3877 0.072 Uiso 1 1 calc R U
B12 B 0.0372(4) 0.5373(5) 0.3412(3) 0.0694(12) Uani 1 1 d . .
H12 H 0.0613 0.4310 0.3901 0.083 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
C4 N3 C2 108.3(3)
C4 N3 C12 126.7(3)
C2 N3 C12 123.0(3)
C5 C1 C2 103.3(2)
C5 C1 B5 131.3(3)
C2 C1 B5 111.3(2)
C5 C1 B4 132.6(3)
C2 C1 B4 111.1(2)
B5 C1 B4 63.0(2)
C5 C1 B3 113.1(3)
C2 C1 B3 62.5(2)
B5 C1 B3 112.9(3)
B4 C1 B3 60.6(2)
C5 C1 B6 111.3(3)
C2 C1 B6 62.18(18)
B5 C1 B6 61.2(2)
B4 C1 B6 113.3(2)
B3 C1 B6 114.5(2)
N3 C2 C1 104.2(2)
N3 C2 B11 129.8(3)
C1 C2 B11 112.1(2)
N3 C2 B7 131.2(3)
C1 C2 B7 111.9(2)
B11 C2 B7 63.2(2)
N3 C2 B6 111.5(3)
C1 C2 B6 62.75(18)
B11 C2 B6 61.2(2)
B7 C2 B6 113.7(2)
N3 C2 B3 113.6(3)
C1 C2 B3 62.4(2)
B11 C2 B3 113.6(3)
B7 C2 B3 61.2(2)
B6 C2 B3 114.9(2)
C5 C4 N3 115.3(3)
C4 C5 C1 108.7(3)
C4 C5 C11 127.6(3)
C1 C5 C11 123.4(3)
B8 B3 B4 61.5(2)
B8 B3 C1 105.3(3)
B4 B3 C1 58.8(2)
B8 B3 C2 104.7(3)
B4 B3 C2 103.6(3)
C1 B3 C2 55.04(18)
B8 B3 B7 61.3(3)
B4 B3 B7 110.0(3)
C1 B3 B7 103.5(3)
C2 B3 B7 58.2(2)
C1 B4 B3 60.6(2)
C1 B4 B9 104.0(3)
B3 B4 B9 107.3(3)
C1 B4 B8 104.8(3)
B3 B4 B8 59.1(2)
B9 B4 B8 59.4(2)
C1 B4 B5 58.4(2)
B3 B4 B5 109.2(3)
B9 B4 B5 59.6(2)
B8 B4 B5 107.4(3)
C1 B5 B6 60.59(19)
C1 B5 B9 104.3(3)
B6 B5 B9 107.0(3)
C1 B5 B10 104.7(2)
B6 B5 B10 58.6(2)
B9 B5 B10 59.6(2)
C1 B5 B4 58.7(2)
B6 B5 B4 109.2(3)
B9 B5 B4 59.7(2)
B10 B5 B4 107.6(3)
B10 B6 C2 104.9(3)
B10 B6 C1 105.0(3)
C2 B6 C1 55.07(17)
B10 B6 B11 61.6(2)
C2 B6 B11 58.21(19)
C1 B6 B11 103.4(2)
B10 B6 B5 61.4(2)
C2 B6 B5 103.1(2)
C1 B6 B5 58.18(19)
B11 B6 B5 109.8(3)
C2 B7 B3 60.7(2)
C2 B7 B12 104.0(3)
B3 B7 B12 107.2(3)
C2 B7 B8 104.8(3)
B3 B7 B8 58.9(2)
B12 B7 B8 59.4(3)
C2 B7 B11 58.3(2)
B3 B7 B11 109.1(3)
B12 B7 B11 59.8(2)
B8 B7 B11 107.5(3)
B3 B8 B9 107.9(3)
B3 B8 B12 108.3(3)
B9 B8 B12 61.2(3)
B3 B8 B7 59.8(2)
B9 B8 B7 108.4(3)
B12 B8 B7 59.9(3)
B3 B8 B4 59.4(2)
B9 B8 B4 59.9(2)
B12 B8 B4 108.6(3)
B7 B8 B4 107.2(3)
B8 B9 B10 108.4(3)
B8 B9 B5 109.3(3)
B10 B9 B5 60.7(2)
B8 B9 B4 60.7(2)
B10 B9 B4 109.3(3)
B5 B9 B4 60.7(2)
B8 B9 B12 59.4(2)
B10 B9 B12 59.7(2)
B5 B9 B12 108.1(3)
B4 B9 B12 107.9(3)
B6 B10 B9 108.2(3)
B6 B10 B12 108.1(3)
B9 B10 B12 60.9(2)
B6 B10 B11 59.6(2)
B9 B10 B11 108.0(3)
B12 B10 B11 59.7(2)
B6 B10 B5 60.0(2)
B9 B10 B5 59.7(2)
B12 B10 B5 108.2(3)
B11 B10 B5 107.2(3)
C2 B11 B6 60.61(19)
C2 B11 B12 104.2(3)
B6 B11 B12 107.4(3)
C2 B11 B7 58.5(2)
B6 B11 B7 109.4(3)
B12 B11 B7 59.7(2)
C2 B11 B10 104.6(2)
B6 B11 B10 58.8(2)
B12 B11 B10 59.7(2)
B7 B11 B10 107.6(3)
B8 B12 B7 60.7(3)
B8 B12 B10 108.2(3)
B7 B12 B10 109.0(3)
B8 B12 B11 109.1(3)
B7 B12 B11 60.5(2)
B10 B12 B11 60.6(2)
B8 B12 B9 59.4(2)
B7 B12 B9 107.6(3)
B10 B12 B9 59.4(2)
B11 B12 B9 107.6(3)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
N3 C4 1.379(4)
N3 C2 1.427(4)
N3 C12 1.450(4)
C1 C5 1.451(4)
C1 C2 1.614(4)
C1 B5 1.707(5)
C1 B4 1.713(5)
C1 B3 1.746(5)
C1 B6 1.750(4)
C2 B11 1.699(5)
C2 B7 1.703(5)
C2 B6 1.741(5)
C2 B3 1.748(5)
C4 C5 1.343(4)
C5 C11 1.458(4)
B3 B8 1.740(6)
B3 B4 1.745(6)
B3 B7 1.756(6)
B4 B9 1.768(6)
B4 B8 1.782(6)
B4 B5 1.787(6)
B5 B6 1.761(5)
B5 B9 1.767(5)
B5 B10 1.785(5)
B6 B10 1.736(5)
B6 B11 1.751(5)
B7 B12 1.768(6)
B7 B8 1.781(6)
B7 B11 1.783(6)
B8 B9 1.759(6)
B8 B12 1.759(7)
B9 B10 1.765(6)
B9 B12 1.790(6)
B10 B12 1.769(6)
B10 B11 1.785(5)
B11 B12 1.769(6)
