#------------------------------------------------------------------------------
#$Date: 2017-03-04 13:55:48 +0100 (Sat 04 de Mar de 2017) $
#$Revision: 193368 $
#$URL: svn://www.crystallography.net/cod/cif/1/54/54/1545449.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_1545449
loop_
_publ_author_name
'Li, Huan-Huan'
'Bai, Fan'
'Yan, Hong'
'Lu, Chang-Sheng'
_publ_section_title
;
 Base-Promoted Decarboxylative Azo-Coupling: Construction of Unsymmetrical
 Azocarboranes.
;
_journal_issue                   4
_journal_name_full               'Organic letters'
_journal_page_first              862
_journal_page_last               865
_journal_paper_doi               10.1021/acs.orglett.7b00013
_journal_volume                  19
_journal_year                    2017
_chemical_formula_sum            'C10 H16 B10 N2'
_chemical_formula_weight         272.35
_chemical_name_systematic
; 
 ? 
;
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2yn'
_symmetry_space_group_name_H-M   'P 1 21/n 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                90.00
_cell_angle_beta                 95.029(3)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   7.5719(14)
_cell_length_b                   20.281(4)
_cell_length_c                   10.3153(18)
_cell_measurement_reflns_used    2956
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      25.51
_cell_measurement_theta_min      2.22
_cell_volume                     1578.0(5)
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      296(2)
_diffrn_measured_fraction_theta_full 0.995
_diffrn_measured_fraction_theta_max 0.995
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0480
_diffrn_reflns_av_sigmaI/netI    0.0393
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       26
_diffrn_reflns_limit_k_min       -26
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -9
_diffrn_reflns_number            14567
_diffrn_reflns_theta_full        27.77
_diffrn_reflns_theta_max         27.77
_diffrn_reflns_theta_min         2.01
_exptl_absorpt_coefficient_mu    0.058
_exptl_absorpt_correction_T_max  0.9838
_exptl_absorpt_correction_T_min  0.9838
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   sadabs
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.146
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             560
_exptl_crystal_size_max          0.28
_exptl_crystal_size_mid          0.28
_exptl_crystal_size_min          0.28
_refine_diff_density_max         0.217
_refine_diff_density_min         -0.194
_refine_diff_density_rms         0.038
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.034
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     207
_refine_ls_number_reflns         3694
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.034
_refine_ls_R_factor_all          0.0836
_refine_ls_R_factor_gt           0.0530
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.1081P)²+0.1389P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1572
_refine_ls_wR_factor_ref         0.1882
_reflns_number_gt                2484
_reflns_number_total             3694
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ol7b00013_si_002.cif
_cod_data_source_block           3as
_cod_depositor_comments
;
The following automatic conversions were performed:

'_symmetry_cell_setting' value 'Monoclinic' changed to 'monoclinic'
according to
/home/data/users/saulius/crontab/automatic-downloads/current/ACS/lib/dictionaries/cif_core.dic
dictionary named 'cif_core.dic' version 2.4.2 from 2011-04-26.

Automatic conversion script
Id: cif_fix_values 4973 2017-02-22 13:04:09Z antanas 
;
_cod_original_sg_symbol_H-M      'P2(1)/n  '
_cod_database_code               1545449
loop_
_symmetry_equiv_pos_as_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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
B3 B 0.5363(3) 0.19652(10) 0.8275(2) 0.0530(5) Uani 1 1 d .
H3 H 0.6035 0.2020 0.7378 0.064 Uiso 1 1 calc R
B6 B 0.2303(3) 0.14783(10) 0.9474(2) 0.0544(5) Uani 1 1 d .
H6 H 0.1020 0.1222 0.9340 0.065 Uiso 1 1 calc R
C3 C 0.2804(2) 0.03777(8) 0.58024(15) 0.0406(4) Uani 1 1 d .
C8 C 0.1906(2) 0.05445(8) 0.46277(15) 0.0433(4) Uani 1 1 d .
H8A H 0.1521 0.0975 0.4478 0.052 Uiso 1 1 calc R
N1 N 0.3940(2) 0.07591(7) 0.77316(13) 0.0479(4) Uani 1 1 d .
C4 C 0.3406(2) -0.02600(8) 0.60505(17) 0.0473(4) Uani 1 1 d .
H4A H 0.4012 -0.0369 0.6845 0.057 Uiso 1 1 calc R
C1 C 0.4128(2) 0.12941(8) 0.86604(15) 0.0432(4) Uani 1 1 d .
C2 C 0.3123(2) 0.20013(8) 0.83735(17) 0.0462(4) Uani 1 1 d .
C6 C 0.2183(2) -0.05680(9) 0.39137(17) 0.0524(5) Uani 1 1 d .
H6A H 0.1977 -0.0891 0.3278 0.063 Uiso 1 1 calc R
C7 C 0.1577(2) 0.00678(9) 0.36655(15) 0.0452(4) Uani 1 1 d .
C5 C 0.3084(3) -0.07298(8) 0.50865(18) 0.0541(5) Uani 1 1 d .
H5A H 0.3481 -0.1160 0.5233 0.065 Uiso 1 1 calc R
B12 B 0.4448(3) 0.24952(11) 1.0704(2) 0.0602(6) Uani 1 1 d .
H12 H 0.4563 0.2903 1.1409 0.072 Uiso 1 1 calc R
B11 B 0.2464(3) 0.23403(10) 0.9735(2) 0.0566(6) Uani 1 1 d .
H11 H 0.1275 0.2648 0.9782 0.068 Uiso 1 1 calc R
B7 B 0.4335(3) 0.26373(10) 0.9011(2) 0.0566(6) Uani 1 1 d .
H7 H 0.4357 0.3136 0.8591 0.068 Uiso 1 1 calc R
B5 B 0.4223(4) 0.11038(11) 1.0260(2) 0.0627(6) Uani 1 1 d .
H5 H 0.4191 0.0600 1.0654 0.075 Uiso 1 1 calc R
B10 B 0.3191(4) 0.17754(13) 1.0985(2) 0.0685(7) Uani 1 1 d .
H10 H 0.2485 0.1713 1.1865 0.082 Uiso 1 1 calc R
B8 B 0.6242(3) 0.22635(12) 0.9803(3) 0.0649(6) Uani 1 1 d .
H8 H 0.7528 0.2519 0.9918 0.078 Uiso 1 1 calc R
B9 B 0.5536(4) 0.17332(13) 1.1024(2) 0.0711(7) Uani 1 1 d .
H9 H 0.6365 0.1645 1.1938 0.085 Uiso 1 1 calc R
B4 B 0.6089(3) 0.14027(12) 0.9523(2) 0.0613(6) Uani 1 1 d .
H4 H 0.7264 0.1092 0.9439 0.074 Uiso 1 1 calc R
N2 N 0.30390(19) 0.09042(7) 0.67234(13) 0.0443(4) Uani 1 1 d .
C9 C 0.0578(3) 0.02272(10) 0.24580(17) 0.0548(5) Uani 1 1 d .
C10 C -0.0286(4) 0.03408(14) 0.1498(2) 0.0775(7) Uani 1 1 d .
H2 H 0.250(3) 0.2035(9) 0.7570(19) 0.055(5) Uiso 1 1 d .
H10A H -0.095(4) 0.0371(17) 0.081(3) 0.132(12) 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
C2 B3 C1 57.12(10)
C2 B3 B8 103.36(16)
C1 B3 B8 103.63(16)
C2 B3 B4 103.35(16)
C1 B3 B4 57.45(11)
B8 B3 B4 60.17(13)
C2 B3 B7 57.75(11)
C1 B3 B7 103.99(16)
B8 B3 B7 59.95(13)
B4 B3 B7 107.70(16)
C2 B6 C1 57.07(11)
C2 B6 B10 104.16(15)
C1 B6 B10 104.34(16)
C2 B6 B11 57.63(12)
C1 B6 B11 103.96(15)
B10 B6 B11 60.59(13)
C2 B6 B5 103.81(16)
C1 B6 B5 57.88(12)
B10 B6 B5 60.30(13)
B11 B6 B5 108.12(15)
C8 C3 C4 121.31(15)
C8 C3 N2 115.08(14)
C4 C3 N2 123.61(14)
C3 C8 C7 119.99(15)
N2 N1 C1 113.34(13)
C5 C4 C3 118.35(16)
N1 C1 C2 121.33(12)
N1 C1 B4 118.74(14)
C2 C1 B4 110.88(13)
N1 C1 B5 117.96(14)
C2 C1 B5 110.83(14)
B4 C1 B5 63.41(14)
N1 C1 B3 117.71(15)
C2 C1 B3 61.19(11)
B4 C1 B3 62.88(13)
B5 C1 B3 115.44(14)
N1 C1 B6 116.74(14)
C2 C1 B6 61.16(11)
B4 C1 B6 115.11(15)
B5 C1 B6 62.61(14)
B3 C1 B6 114.70(14)
C1 C2 B11 112.01(14)
C1 C2 B7 111.83(13)
B11 C2 B7 63.32(13)
C1 C2 B3 61.69(11)
B11 C2 B3 115.89(14)
B7 C2 B3 63.03(12)
C1 C2 B6 61.76(11)
B11 C2 B6 63.02(12)
B7 C2 B6 115.67(14)
B3 C2 B6 115.64(14)
C5 C6 C7 121.03(15)
C6 C7 C8 118.63(15)
C6 C7 C9 120.70(15)
C8 C7 C9 120.64(16)
C6 C5 C4 120.69(16)
B11 B12 B7 60.09(13)
B11 B12 B9 108.09(15)
B7 B12 B9 107.99(17)
B11 B12 B8 108.04(16)
B7 B12 B8 59.86(14)
B9 B12 B8 60.09(15)
B11 B12 B10 60.24(13)
B7 B12 B10 108.33(14)
B9 B12 B10 60.00(16)
B8 B12 B10 108.24(16)
C2 B11 B12 104.30(16)
C2 B11 B7 58.45(12)
B12 B11 B7 60.14(13)
C2 B11 B6 59.35(11)
B12 B11 B6 107.85(15)
B7 B11 B6 108.64(15)
C2 B11 B10 104.33(15)
B12 B11 B10 60.50(14)
B7 B11 B10 108.58(17)
B6 B11 B10 59.10(13)
C2 B7 B11 58.23(12)
C2 B7 B12 103.84(16)
B11 B7 B12 59.77(14)
C2 B7 B8 104.32(14)
B11 B7 B8 108.18(17)
B12 B7 B8 60.36(14)
C2 B7 B3 59.22(11)
B11 B7 B3 108.53(15)
B12 B7 B3 108.24(15)
B8 B7 B3 59.75(13)
C1 B5 B9 104.21(17)
C1 B5 B10 104.75(15)
B9 B5 B10 60.37(15)
C1 B5 B4 57.94(12)
B9 B5 B4 60.22(15)
B10 B5 B4 108.49(17)
C1 B5 B6 59.51(12)
B9 B5 B6 107.59(16)
B10 B5 B6 59.22(13)
B4 B5 B6 108.09(15)
B6 B10 B5 60.49(13)
B6 B10 B9 107.99(17)
B5 B10 B9 59.61(15)
B6 B10 B11 60.32(12)
B5 B10 B11 108.05(16)
B9 B10 B11 107.05(18)
B6 B10 B12 107.84(17)
B5 B10 B12 107.46(19)
B9 B10 B12 59.66(15)
B11 B10 B12 59.26(13)
B3 B8 B7 60.31(12)
B3 B8 B4 60.13(12)
B7 B8 B4 107.95(14)
B3 B8 B9 108.23(16)
B7 B8 B9 107.64(18)
B4 B8 B9 59.93(14)
B3 B8 B12 108.21(15)
B7 B8 B12 59.77(14)
B4 B8 B12 107.69(18)
B9 B8 B12 59.75(15)
B5 B9 B12 108.33(16)
B5 B9 B4 60.13(14)
B12 B9 B4 108.03(16)
B5 B9 B8 108.36(15)
B12 B9 B8 60.16(15)
B4 B9 B8 59.95(15)
B5 B9 B10 60.03(14)
B12 B9 B10 60.34(14)
B4 B9 B10 108.15(15)
B8 B9 B10 108.55(16)
C1 B4 B5 58.65(12)
C1 B4 B3 59.67(11)
B5 B4 B3 108.92(15)
C1 B4 B9 104.31(17)
B5 B4 B9 59.65(15)
B3 B4 B9 108.03(16)
C1 B4 B8 104.96(14)
B5 B4 B8 108.11(17)
B3 B4 B8 59.70(13)
B9 B4 B8 60.12(15)
N1 N2 C3 114.28(13)
C10 C9 C7 177.2(2)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
B3 C2 1.709(3)
B3 C1 1.717(3)
B3 B8 1.763(3)
B3 B4 1.771(3)
B3 B7 1.773(3)
B6 C2 1.710(3)
B6 C1 1.720(3)
B6 B10 1.749(3)
B6 B11 1.771(3)
B6 B5 1.772(3)
C3 C8 1.378(2)
C3 C4 1.388(2)
C3 N2 1.430(2)
C8 C7 1.392(2)
N1 N2 1.2286(17)
N1 C1 1.446(2)
C4 C5 1.383(2)
C1 C2 1.638(2)
C1 B4 1.677(2)
C1 B5 1.690(3)
C2 B11 1.679(3)
C2 B7 1.683(2)
C6 C5 1.376(2)
C6 C7 1.385(3)
C7 C9 1.436(2)
B12 B11 1.759(3)
B12 B7 1.765(3)
B12 B9 1.768(3)
B12 B8 1.776(4)
B12 B10 1.781(4)
B11 B7 1.764(4)
B11 B10 1.776(3)
B7 B8 1.767(3)
B5 B9 1.761(3)
B5 B10 1.769(4)
B5 B4 1.770(4)
B10 B9 1.775(4)
B8 B4 1.772(3)
B8 B9 1.775(4)
B9 B4 1.771(4)
C9 C10 1.161(3)
