#------------------------------------------------------------------------------
#$Date: 2017-11-28 10:32:20 +0200 (Tue, 28 Nov 2017) $
#$Revision: 203690 $
#$URL: file:///home/coder/svn-repositories/cod/cif/1/54/82/1548257.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_1548257
loop_
_publ_author_name
'Baolin Wang'
'Yongxin Li'
'Rakesh Ganguly'
'Hajime Hirao'
'Rei Kinjo'
_publ_section_title
;
 Ambiphilic boron in 1,4,2,5-diazadiborinine
;
_journal_name_full               'Nature Communications'
_journal_page_first              11871
_journal_paper_doi               10.1038/ncomms11871
_journal_volume                  7
_journal_year                    2016
_chemical_formula_sum            'C20 H20 B2 N4'
_chemical_formula_weight         338.02
_space_group_crystal_system      monoclinic
_space_group_IT_number           15
_space_group_name_Hall           '-C 2yc'
_space_group_name_H-M_alt        'C 1 2/c 1'
_symmetry_space_group_name_Hall  '-C 2yc'
_symmetry_space_group_name_H-M   'C 1 2/c 1'
_atom_sites_solution_hydrogens   geom
_cell_angle_alpha                90
_cell_angle_beta                 132.202(4)
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   28.875(4)
_cell_length_b                   8.4730(15)
_cell_length_c                   19.549(3)
_cell_measurement_reflns_used    1878
_cell_measurement_temperature    103.(2)
_cell_measurement_theta_max      23.2262
_cell_measurement_theta_min      2.8130
_cell_volume                     3543.0(10)
_computing_cell_refinement       'SAINT V8.34A (Bruker AXS Inc., 2013)'
_computing_data_collection       'APEX2 (Bruker AXS Inc., 2014)'
_computing_data_reduction        'SAINT V8.34A (Bruker AXS Inc., 2013)'
_computing_molecular_graphics    'XP (Bruker AXS Inc., 2014)'
_computing_publication_material  'APEX2 (Bruker AXS Inc., 2014)'
_computing_structure_refinement  'SHELXL-2014/6 (Sheldrick, 2014)'
_computing_structure_solution    'SHELXT (Bruker AXS Inc., 2014)'
_diffrn_ambient_temperature      103.(2)
_diffrn_detector_area_resol_mean 8.3333
_diffrn_measured_fraction_theta_full 0.996
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0649
_diffrn_reflns_av_unetI/netI     0.0726
_diffrn_reflns_limit_h_max       39
_diffrn_reflns_limit_h_min       -38
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       26
_diffrn_reflns_limit_l_min       -26
_diffrn_reflns_number            17195
_diffrn_reflns_theta_full        29.13
_diffrn_reflns_theta_max         29.13
_diffrn_reflns_theta_min         1.90
_diffrn_source                   'fine-focus sealed tube'
_exptl_absorpt_coefficient_mu    0.075
_exptl_absorpt_correction_T_max  0.99
_exptl_absorpt_correction_T_min  0.78
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS V2014/4 (Bruker AXS Inc.)'
_exptl_crystal_colour            orange
_exptl_crystal_density_diffrn    1.267
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             1424
_exptl_crystal_size_max          0.240
_exptl_crystal_size_mid          0.180
_exptl_crystal_size_min          0.160
_refine_diff_density_max         0.340
_refine_diff_density_min         -0.264
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.015
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     237
_refine_ls_number_reflns         4769
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.015
_refine_ls_R_factor_all          0.0913
_refine_ls_R_factor_gt           0.0538
_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)+(0.0417P)²+2.8295P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1094
_refine_ls_wR_factor_ref         0.1261
_reflns_number_gt                3192
_reflns_number_total             4769
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            ncomms11871-s3.cif
_cod_data_source_block           II
_cod_database_code               1548257
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y, -z+1/2'
'x+1/2, y+1/2, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y, z-1/2'
'-x+1/2, -y+1/2, -z'
'x+1/2, -y+1/2, z-1/2'
loop_
_atom_site_type_symbol
_atom_site_label
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_calc_flag
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_refinement_flags_posn
_atom_site_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
B B1 0.22562(8) 0.3409(2) 0.03736(13) 0.0137(4) Uani d . . . 1 . .
B B2 0.53668(9) 0.3982(2) 0.58625(13) 0.0141(4) Uani d . . . 1 . .
C C1 0.29125(7) 0.3263(2) -0.00558(11) 0.0133(3) Uani d . . . 1 . .
C C2 0.29047(8) 0.5631(2) 0.04808(12) 0.0158(4) Uani d . . . 1 . .
H H2 0.282 0.6438 0.0721 0.019 Uiso calc U . R 1 . .
C C3 0.32601(8) 0.5785(2) 0.02690(12) 0.0171(4) Uani d . . . 1 . .
H H3 0.3467 0.6721 0.0332 0.021 Uiso calc U . R 1 . .
C C4 0.35951(9) 0.4078(2) -0.03760(14) 0.0247(4) Uani d . . . 1 . .
H H4A 0.3843 0.5009 -0.0253 0.037 Uiso calc U . R 1 . .
H H4B 0.3287 0.3868 -0.1041 0.037 Uiso calc U . R 1 . .
H H4C 0.3872 0.3164 -0.0052 0.037 Uiso calc U . R 1 . .
C C5 0.19989(8) 0.4554(2) 0.06950(12) 0.0157(4) Uani d . . . 1 . .
C C6 0.13620(8) 0.4977(2) 0.00830(12) 0.0168(4) Uani d . . . 1 . .
H H6 0.1082 0.4498 -0.051 0.02 Uiso calc U . R 1 . .
C C7 0.11282(8) 0.6072(2) 0.03154(13) 0.0194(4) Uani d . . . 1 . .
H H7 0.0697 0.6335 -0.0119 0.023 Uiso calc U . R 1 . .
C C8 0.15219(9) 0.6778(2) 0.11771(14) 0.0224(4) Uani d . . . 1 . .
H H8 0.1363 0.7519 0.134 0.027 Uiso calc U . R 1 . .
C C9 0.21525(9) 0.6388(2) 0.17999(14) 0.0254(4) Uani d . . . 1 . .
H H9 0.2427 0.6865 0.2394 0.03 Uiso calc U . R 1 . .
C C10 0.23840(8) 0.5302(2) 0.15592(13) 0.0208(4) Uani d . . . 1 . .
H H10 0.2818 0.5059 0.1995 0.025 Uiso calc U . R 1 . .
C C11 0.47492(7) 0.4295(2) 0.41468(11) 0.0133(3) Uani d . . . 1 . .
C C12 0.51163(8) 0.1840(2) 0.47415(12) 0.0152(3) Uani d . . . 1 . .
H H12 0.5325 0.0984 0.5164 0.018 Uiso calc U . R 1 . .
C C13 0.47892(8) 0.1763(2) 0.38288(12) 0.0171(4) Uani d . . . 1 . .
H H13 0.4726 0.0841 0.3499 0.021 Uiso calc U . R 1 . .
C C14 0.41581(9) 0.3612(2) 0.24809(12) 0.0267(4) Uani d . . . 1 . .
H H14A 0.3988 0.2633 0.212 0.04 Uiso calc U . R 1 . .
H H14B 0.4399 0.4168 0.2369 0.04 Uiso calc U . R 1 . .
H H14C 0.3814 0.4285 0.2295 0.04 Uiso calc U . R 1 . .
C C15 0.57153(7) 0.27925(19) 0.66974(11) 0.0137(3) Uani d . . . 1 . .
C C16 0.54973(8) 0.2516(2) 0.71513(11) 0.0157(3) Uani d . . . 1 . .
H H16 0.5133 0.305 0.6943 0.019 Uiso calc U . R 1 . .
C C17 0.58004(8) 0.1487(2) 0.78940(12) 0.0176(4) Uani d . . . 1 . .
H H17 0.5641 0.1326 0.8184 0.021 Uiso calc U . R 1 . .
C C18 0.63338(8) 0.0692(2) 0.82147(12) 0.0185(4) Uani d . . . 1 . .
H H18 0.6545 0.0003 0.873 0.022 Uiso calc U . R 1 . .
C C19 0.65556(8) 0.0917(2) 0.77740(12) 0.0187(4) Uani d . . . 1 . .
H H19 0.6918 0.0368 0.7984 0.022 Uiso calc U . R 1 . .
C C20 0.62505(8) 0.1938(2) 0.70299(12) 0.0168(4) Uani d . . . 1 . .
H H20 0.6407 0.2067 0.6734 0.02 Uiso calc U . R 1 . .
N N1 0.26801(6) 0.40731(16) 0.02858(9) 0.0127(3) Uani d . . . 1 . .
N N2 0.32742(7) 0.43632(17) -0.00526(10) 0.0160(3) Uani d . . . 1 . .
N N3 0.50960(6) 0.33992(16) 0.49603(9) 0.0123(3) Uani d . . . 1 . .
N N4 0.45616(7) 0.32400(17) 0.34547(10) 0.0164(3) Uani d . . . 1 . .
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_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle
N1 B1 C1 . 7 112.50(15)
N1 B1 C5 . . 117.67(15)
C1 B1 C5 7 . 129.58(15)
N3 B2 C11 . 5_666 112.53(15)
N3 B2 C15 . . 119.22(15)
C11 B2 C15 5_666 . 128.22(15)
N2 C1 N1 . . 105.47(14)
N2 C1 B1 . 7 132.06(15)
N1 C1 B1 . 7 122.41(14)
C3 C2 N1 . . 108.37(15)
C2 C3 N2 . . 108.65(15)
C10 C5 C6 . . 115.74(16)
C10 C5 B1 . . 123.36(15)
C6 C5 B1 . . 120.71(15)
C7 C6 C5 . . 122.36(17)
C8 C7 C6 . . 120.26(17)
C7 C8 C9 . . 119.04(17)
C8 C9 C10 . . 120.36(18)
C9 C10 C5 . . 122.24(17)
N4 C11 N3 . . 105.67(14)
N4 C11 B2 . 5_666 132.63(15)
N3 C11 B2 . 5_666 121.69(14)
C13 C12 N3 . . 108.28(15)
C12 C13 N4 . . 108.67(15)
C20 C15 C16 . . 116.06(15)
C20 C15 B2 . . 123.05(15)
C16 C15 B2 . . 120.88(15)
C17 C16 C15 . . 121.88(16)
C18 C17 C16 . . 120.42(16)
C17 C18 C19 . . 119.22(16)
C20 C19 C18 . . 120.26(16)
C19 C20 C15 . . 122.13(16)
C1 N1 C2 . . 107.90(13)
C1 N1 B1 . . 125.09(14)
C2 N1 B1 . . 126.95(14)
C3 N2 C1 . . 109.61(13)
C3 N2 C4 . . 124.79(14)
C1 N2 C4 . . 125.55(15)
C12 N3 C11 . . 107.94(13)
C12 N3 B2 . . 126.26(14)
C11 N3 B2 . . 125.76(14)
C13 N4 C11 . . 109.43(14)
C13 N4 C14 . . 124.91(15)
C11 N4 C14 . . 125.56(15)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_site_symmetry_2
_geom_bond_distance
B1 N1 . 1.458(2)
B1 C1 7 1.491(3)
B1 C5 . 1.586(2)
B2 N3 . 1.454(2)
B2 C11 5_666 1.496(3)
B2 C15 . 1.576(3)
C1 N2 . 1.397(2)
C1 N1 . 1.403(2)
C1 B1 7 1.491(3)
C2 C3 . 1.346(2)
C2 N1 . 1.406(2)
C3 N2 . 1.372(2)
C4 N2 . 1.450(2)
C5 C10 . 1.403(2)
C5 C6 . 1.409(2)
C6 C7 . 1.391(2)
C7 C8 . 1.384(3)
C8 C9 . 1.389(3)
C9 C10 . 1.392(3)
C11 N4 . 1.392(2)
C11 N3 . 1.403(2)
C11 B2 5_666 1.496(3)
C12 C13 . 1.348(2)
C12 N3 . 1.402(2)
C13 N4 . 1.374(2)
C14 N4 . 1.449(2)
C15 C20 . 1.409(2)
C15 C16 . 1.410(2)
C16 C17 . 1.389(2)
C17 C18 . 1.386(2)
C18 C19 . 1.389(2)
C19 C20 . 1.385(2)
