#------------------------------------------------------------------------------
#$Date: 2017-11-28 10:58:30 +0200 (Tue, 28 Nov 2017) $
#$Revision: 203700 $
#$URL: file:///home/coder/svn-repositories/cod/cif/1/54/82/1548267.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_1548267
loop_
_publ_author_name
'Di Wu'
'Lingbing Kong'
'Yongxin Li'
'Rakesh Ganguly'
'Rei Kinjo'
_publ_section_title
;
 1,3,2,5-Diazadiborinine featuring nucleophilic and electrophilic boron
 centres
;
_journal_name_full               'Nature Communications'
_journal_page_first              7340
_journal_paper_doi               10.1038/ncomms8340
_journal_volume                  6
_journal_year                    2015
_chemical_formula_sum            'C78 H83 B4 F11 N4 O10 S2'
_chemical_formula_weight         1552.84
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -1'
_atom_sites_solution_hydrogens   geom
_cell_angle_alpha                98.334(4)
_cell_angle_beta                 90.656(4)
_cell_angle_gamma                109.608(4)
_cell_formula_units_Z            1
_cell_length_a                   10.8994(10)
_cell_length_b                   13.3303(14)
_cell_length_c                   14.0182(13)
_cell_measurement_reflns_used    3065
_cell_measurement_temperature    103.(2)
_cell_measurement_theta_max      27.7105
_cell_measurement_theta_min      2.4905
_cell_volume                     1894.4(3)
_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)'
_diffrn_ambient_temperature      103.(2)
_diffrn_detector_area_resol_mean 8.3333
_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_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.1022
_diffrn_reflns_av_unetI/netI     0.1471
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            27307
_diffrn_reflns_theta_full        28.32
_diffrn_reflns_theta_max         28.32
_diffrn_reflns_theta_min         2.40
_diffrn_source                   'fine-focus sealed tube'
_exptl_absorpt_coefficient_mu    0.159
_exptl_absorpt_correction_T_max  0.99
_exptl_absorpt_correction_T_min  0.85
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS V2014/4 (Bruker AXS Inc.)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.361
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       plate
_exptl_crystal_F_000             810
_exptl_crystal_size_max          0.420
_exptl_crystal_size_mid          0.100
_exptl_crystal_size_min          0.060
_refine_diff_density_max         1.084
_refine_diff_density_min         -0.466
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.017
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     517
_refine_ls_number_reflns         9409
_refine_ls_number_restraints     61
_refine_ls_restrained_S_all      1.015
_refine_ls_R_factor_all          0.1710
_refine_ls_R_factor_gt           0.0790
_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)+(0.0900P)²+0.4089P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1730
_refine_ls_wR_factor_ref         0.2145
_reflns_number_gt                4639
_reflns_number_total             9409
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            ncomms8340-s4.cif
_cod_data_source_block           III
_cod_database_code               1548267
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'
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 0.6741(4) 0.7561(3) 0.7863(3) 0.0159(8) Uani d . . . 1 . .
B B2 0.4178(4) 0.5488(3) 0.7546(3) 0.0193(9) Uani d . . . 1 . .
C C1 0.4983(3) 0.6134(3) 0.6740(2) 0.0163(7) Uani d . . . 1 . .
C C2 0.4979(3) 0.6123(3) 0.8542(2) 0.0165(7) Uani d . . . 1 . .
C C3 0.8305(3) 0.7949(3) 0.7928(2) 0.0179(8) Uani d . . . 1 . .
C C4 0.8918(3) 0.7176(3) 0.7846(2) 0.0241(8) Uani d . . . 1 . .
H H4 0.8403 0.6432 0.7721 0.029 Uiso calc U . R 1 . .
C C5 1.0264(4) 0.7476(4) 0.7946(3) 0.0366(11) Uani d . . . 1 . .
H H5 1.066 0.6937 0.7891 0.044 Uiso calc U . R 1 . .
C C6 1.1038(4) 0.8550(4) 0.8124(3) 0.0422(12) Uani d . . . 1 . .
H H6 1.196 0.8751 0.8203 0.051 Uiso calc U . R 1 . .
C C7 1.0460(4) 0.9321(4) 0.8186(3) 0.0386(11) Uani d . . . 1 . .
H H7 1.0985 1.0063 0.8299 0.046 Uiso calc U . R 1 . .
C C8 0.9098(3) 0.9024(3) 0.8085(2) 0.0265(9) Uani d . . . 1 . .
H H8 0.8711 0.9569 0.8126 0.032 Uiso calc U . R 1 . .
C C9 0.4281(3) 0.4286(3) 0.7385(2) 0.0171(7) Uani d . . . 1 . .
C C10 0.5483(3) 0.4126(3) 0.7394(2) 0.0211(8) Uani d . . . 1 . .
H H10 0.626 0.4737 0.7503 0.025 Uiso calc U . R 1 . .
C C11 0.5581(4) 0.3104(3) 0.7249(3) 0.0270(9) Uani d . . . 1 . .
H H11 0.6415 0.3025 0.7261 0.032 Uiso calc U . R 1 . .
C C12 0.4469(4) 0.2206(3) 0.7087(3) 0.0281(9) Uani d . . . 1 . .
H H12 0.4532 0.1505 0.698 0.034 Uiso calc U . R 1 . .
C C13 0.3259(4) 0.2330(3) 0.7081(3) 0.0274(9) Uani d . . . 1 . .
H H13 0.2488 0.1713 0.6974 0.033 Uiso calc U . R 1 . .
C C14 0.3174(3) 0.3357(3) 0.7232(2) 0.0209(8) Uani d . . . 1 . .
H H14 0.2336 0.3429 0.7231 0.025 Uiso calc U . R 1 . .
C C15 0.2711(3) 0.5526(3) 0.7536(3) 0.0240(8) Uani d . . . 1 . .
H H15A 0.2746 0.6278 0.761 0.036 Uiso calc U . R 1 . .
H H15B 0.226 0.519 0.807 0.036 Uiso calc U . R 1 . .
H H15C 0.2238 0.5133 0.6921 0.036 Uiso calc U . R 1 . .
C C16 0.5259(3) 0.6656(3) 0.5277(2) 0.0239(8) Uani d . . . 1 . .
H H16A 0.4795 0.7165 0.5199 0.029 Uiso calc U . R 1 . .
H H16B 0.5413 0.6327 0.463 0.029 Uiso calc U . R 1 . .
C C17 0.6539(3) 0.7226(3) 0.5880(2) 0.0200(8) Uani d . . . 1 . .
C C18 0.7553(4) 0.6692(3) 0.5580(3) 0.0274(9) Uani d . . . 1 . .
H H18A 0.7771 0.6785 0.4914 0.041 Uiso calc U . R 1 . .
H H18B 0.7193 0.5921 0.5621 0.041 Uiso calc U . R 1 . .
H H18C 0.8343 0.7029 0.6013 0.041 Uiso calc U . R 1 . .
C C19 0.7046(4) 0.8421(3) 0.5850(2) 0.0261(9) Uani d . . . 1 . .
H H19A 0.6399 0.874 0.6097 0.039 Uiso calc U . R 1 . .
H H19B 0.7203 0.8543 0.5182 0.039 Uiso calc U . R 1 . .
H H19C 0.7864 0.8758 0.6252 0.039 Uiso calc U . R 1 . .
C C20 0.5291(3) 0.6628(3) 1.0160(2) 0.0230(8) Uani d . . . 1 . .
H H20A 0.5404 0.6289 1.0723 0.028 Uiso calc U . R 1 . .
H H20B 0.4888 0.7181 1.0365 0.028 Uiso calc U . R 1 . .
C C21 0.6588(3) 0.7115(3) 0.9722(2) 0.0187(8) Uani d . . . 1 . .
C C22 0.7233(4) 0.8298(3) 1.0141(3) 0.0283(9) Uani d . . . 1 . .
H H22A 0.808 0.8583 0.9866 0.043 Uiso calc U . R 1 . .
H H22B 0.7362 0.8374 1.0844 0.043 Uiso calc U . R 1 . .
H H22C 0.6674 0.8701 0.9984 0.043 Uiso calc U . R 1 . .
C C23 0.7472(3) 0.6463(3) 0.9853(3) 0.0273(9) Uani d . . . 1 . .
H H23A 0.7031 0.571 0.9559 0.041 Uiso calc U . R 1 . .
H H23B 0.7668 0.6499 1.0544 0.041 Uiso calc U . R 1 . .
H H23C 0.8287 0.6762 0.9541 0.041 Uiso calc U . R 1 . .
C C24 0.5636(4) 1.0184(3) 0.8580(3) 0.0319(10) Uani d . . . 1 . .
C C25 0.0820(4) 0.8812(4) 0.4547(4) 0.0506(13) Uani d . . D 1 . .
C C26 0.1738(5) 0.8773(4) 0.3900(3) 0.0487(13) Uani d . . . 1 . .
H H26 0.1529 0.8652 0.3224 0.058 Uiso calc U . R 1 . .
C C27 0.2970(5) 0.8913(4) 0.4257(4) 0.0489(13) Uani d . . . 1 . .
H H27 0.3628 0.8905 0.382 0.059 Uiso calc U . R 1 . .
C C28 0.3267(5) 0.9063(4) 0.5213(3) 0.0505(13) Uani d . . . 1 . .
H H28 0.4122 0.9143 0.5446 0.061 Uiso calc U . R 1 . .
C C29 0.2326(4) 0.9100(4) 0.5851(3) 0.0515(13) Uani d . . . 1 . .
H H29 0.2537 0.9213 0.6526 0.062 Uiso calc U . R 1 . .
C C30 0.1087(4) 0.8975(4) 0.5521(3) 0.0509(13) Uani d . . . 1 . .
H H30 0.0434 0.9002 0.5957 0.061 Uiso calc U . R 1 . .
C C31 0.9573(4) 0.2594(4) 0.8654(3) 0.0364(10) Uani d . . D 1 . .
C C32 0.8977(4) 0.2313(4) 0.9471(3) 0.0444(12) Uani d . . . 1 . .
H H32 0.8997 0.169 0.9717 0.053 Uiso calc U . R 1 . .
C C33 0.8338(4) 0.2974(4) 0.9931(3) 0.0431(12) Uani d . . . 1 . .
H H33 0.7911 0.2805 1.0504 0.052 Uiso calc U . R 1 . .
C C34 0.8321(4) 0.3856(4) 0.9569(3) 0.0439(12) Uani d . . . 1 . .
H H34 0.7878 0.4297 0.9893 0.053 Uiso calc U . R 1 . .
C C35 0.8934(4) 0.4129(4) 0.8737(3) 0.0426(11) Uani d . . . 1 . .
H H35 0.893 0.4759 0.8497 0.051 Uiso calc U . R 1 . .
C C36 0.9557(4) 0.3466(4) 0.8259(3) 0.0393(11) Uani d . . . 1 . .
H H36 0.996 0.3616 0.7673 0.047 Uiso calc U . R 1 . .
F F6 -0.0829(9) 0.5007(6) 0.6751(5) 0.105(3) Uani d U P D 0.5 A -1
C C37 -0.0451(15) 0.4991(13) 0.5856(11) 0.051(3) Uani d U P DG 0.5 A -1
C C38 0.0470(16) 0.5891(13) 0.5581(11) 0.056(3) Uani d U P DG 0.5 A -1
H H38 0.0828 0.6534 0.6035 0.068 Uiso calc U P R 0.5 A -1
C C39 0.0869(19) 0.5852(15) 0.4642(11) 0.078(5) Uani d U P G 0.5 A -1
H H39 0.15 0.6468 0.4455 0.094 Uiso calc U P R 0.5 A -1
C C40 0.035(2) 0.4912(17) 0.3978(11) 0.091(6) Uani d U P G 0.5 A -1
H H40 0.0619 0.4886 0.3337 0.109 Uiso calc U P R 0.5 A -1
C C41 -0.058(2) 0.4012(15) 0.4253(11) 0.084(6) Uani d U P G 0.5 A -1
H H41 -0.0932 0.3369 0.3799 0.101 Uiso calc U P R 0.5 A -1
C C42 -0.0974(17) 0.4051(13) 0.5191(11) 0.063(4) Uani d U P DG 0.5 A -1
H H42 -0.1604 0.3435 0.5379 0.076 Uiso calc U P R 0.5 A -1
F F1 0.6430(2) 1.07526(19) 0.79804(17) 0.0429(7) Uani d . . . 1 . .
F F2 0.6257(2) 1.03821(18) 0.94302(16) 0.0375(6) Uani d . . . 1 . .
F F3 0.4613(2) 1.0505(2) 0.86597(19) 0.0487(7) Uani d . . . 1 . .
F F4 -0.0391(3) 0.8695(3) 0.4214(2) 0.0922(12) Uani d . . D 1 . .
F F5 1.0189(3) 0.1949(3) 0.8217(2) 0.0723(9) Uani d . . D 1 . .
N N1 0.6076(3) 0.6944(2) 0.68613(18) 0.0146(6) Uani d . . . 1 . .
N N2 0.6106(2) 0.6896(2) 0.86602(18) 0.0138(6) Uani d . . . 1 . .
O O1 0.4510(2) 0.5823(2) 0.58301(16) 0.0232(6) Uani d . . . 1 . .
O O2 0.4501(2) 0.5818(2) 0.93665(15) 0.0210(6) Uani d . . . 1 . .
O O3 0.6403(2) 0.86230(19) 0.80428(16) 0.0181(5) Uani d . . . 1 . .
O O4 0.4462(3) 0.8637(3) 0.71719(19) 0.0411(8) Uani d . . . 1 . .
O O5 0.4328(2) 0.8228(2) 0.88211(18) 0.0289(6) Uani d . . . 1 . .
S S1 0.50788(9) 0.87488(8) 0.80959(6) 0.0232(2) 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'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
F F 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
S S 0.1246 0.1234 '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
N2 B1 N1 . . 109.3(3)
N2 B1 O3 . . 106.4(2)
N1 B1 O3 . . 106.6(3)
N2 B1 C3 . . 113.8(3)
N1 B1 C3 . . 114.9(3)
O3 B1 C3 . . 105.2(3)
C2 B2 C1 . . 104.0(3)
C2 B2 C15 . . 110.8(3)
C1 B2 C15 . . 110.4(3)
C2 B2 C9 . . 107.5(3)
C1 B2 C9 . . 108.2(3)
C15 B2 C9 . . 115.3(3)
N1 C1 O1 . . 113.9(3)
N1 C1 B2 . . 128.1(3)
O1 C1 B2 . . 118.0(3)
N2 C2 O2 . . 113.7(3)
N2 C2 B2 . . 127.7(3)
O2 C2 B2 . . 118.5(3)
C8 C3 C4 . . 117.4(3)
C8 C3 B1 . . 123.4(3)
C4 C3 B1 . . 119.2(3)
C5 C4 C3 . . 121.1(4)
C6 C5 C4 . . 120.8(4)
C7 C6 C5 . . 119.2(4)
C6 C7 C8 . . 120.4(4)
C3 C8 C7 . . 121.2(4)
C10 C9 C14 . . 116.2(3)
C10 C9 B2 . . 121.8(3)
C14 C9 B2 . . 122.0(3)
C11 C10 C9 . . 122.3(3)
C12 C11 C10 . . 120.0(4)
C11 C12 C13 . . 119.6(4)
C12 C13 C14 . . 119.9(4)
C13 C14 C9 . . 122.1(3)
O1 C16 C17 . . 104.4(3)
C19 C17 C16 . . 112.1(3)
C19 C17 N1 . . 113.7(3)
C16 C17 N1 . . 98.8(2)
C19 C17 C18 . . 112.1(3)
C16 C17 C18 . . 110.7(3)
N1 C17 C18 . . 108.7(3)
O2 C20 C21 . . 103.4(2)
C22 C21 C20 . . 111.2(3)
C22 C21 C23 . . 112.0(3)
C20 C21 C23 . . 110.1(3)
C22 C21 N2 . . 114.9(3)
C20 C21 N2 . . 99.1(3)
C23 C21 N2 . . 108.8(3)
F2 C24 F3 . . 109.2(3)
F2 C24 F1 . . 108.9(3)
F3 C24 F1 . . 108.0(3)
F2 C24 S1 . . 111.3(3)
F3 C24 S1 . . 108.9(3)
F1 C24 S1 . . 110.5(3)
F4 C25 C30 . . 118.4(4)
F4 C25 C26 . . 119.1(5)
C30 C25 C26 . . 122.5(4)
C25 C26 C27 . . 117.9(4)
C28 C27 C26 . . 121.4(4)
C27 C28 C29 . . 119.6(5)
C30 C29 C28 . . 120.6(5)
C25 C30 C29 . . 117.9(4)
F5 C31 C32 . . 116.7(4)
F5 C31 C36 . . 119.4(4)
C32 C31 C36 . . 123.9(4)
C31 C32 C33 . . 117.3(4)
C34 C33 C32 . . 120.5(4)
C33 C34 C35 . . 121.4(4)
C34 C35 C36 . . 118.9(5)
C31 C36 C35 . . 118.0(4)
F6 C37 C38 . . 120.9(7)
F6 C37 C42 . . 119.1(7)
C38 C37 C42 . . 120.0
C39 C38 C37 . . 120.0
C38 C39 C40 . . 120.0
C41 C40 C39 . . 120.0
C40 C41 C42 . . 120.0
C41 C42 C37 . . 120.0
C1 N1 C17 . . 109.6(3)
C1 N1 B1 . . 124.2(3)
C17 N1 B1 . . 126.1(3)
C2 N2 C21 . . 108.8(3)
C2 N2 B1 . . 124.2(3)
C21 N2 B1 . . 126.7(3)
C1 O1 C16 . . 107.3(3)
C2 O2 C20 . . 107.4(3)
S1 O3 B1 . . 128.7(2)
O4 S1 O5 . . 118.84(17)
O4 S1 O3 . . 112.74(14)
O5 S1 O3 . . 113.29(15)
O4 S1 C24 . . 106.2(2)
O5 S1 C24 . . 105.27(16)
O3 S1 C24 . . 97.52(16)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_site_symmetry_2
_geom_bond_distance
B1 N2 . 1.551(5)
B1 N1 . 1.554(4)
B1 O3 . 1.566(5)
B1 C3 . 1.603(5)
B2 C2 . 1.600(5)
B2 C1 . 1.608(5)
B2 C15 . 1.617(5)
B2 C9 . 1.627(5)
C1 N1 . 1.301(4)
C1 O1 . 1.325(4)
C2 N2 . 1.302(4)
C2 O2 . 1.334(4)
C3 C8 . 1.386(5)
C3 C4 . 1.397(5)
C4 C5 . 1.385(5)
C5 C6 . 1.380(6)
C6 C7 . 1.368(6)
C7 C8 . 1.402(5)
C9 C10 . 1.397(5)
C9 C14 . 1.397(5)
C10 C11 . 1.388(5)
C11 C12 . 1.377(5)
C12 C13 . 1.383(5)
C13 C14 . 1.389(5)
C16 O1 . 1.468(4)
C16 C17 . 1.521(5)
C17 C19 . 1.509(5)
C17 N1 . 1.525(4)
C17 C18 . 1.535(5)
C20 O2 . 1.466(4)
C20 C21 . 1.522(5)
C21 C22 . 1.518(5)
C21 C23 . 1.523(5)
C21 N2 . 1.527(4)
C24 F2 . 1.311(5)
C24 F3 . 1.322(4)
C24 F1 . 1.338(4)
C24 S1 . 1.823(4)
C25 F4 . 1.346(5)
C25 C30 . 1.363(6)
C25 C26 . 1.367(6)
C26 C27 . 1.370(6)
C27 C28 . 1.345(6)
C28 C29 . 1.378(6)
C29 C30 . 1.370(6)
C31 F5 . 1.345(5)
C31 C32 . 1.360(6)
C31 C36 . 1.364(6)
C32 C33 . 1.392(6)
C33 C34 . 1.352(6)
C34 C35 . 1.386(6)
C35 C36 . 1.390(6)
F6 C37 . 1.325(13)
C37 C38 . 1.39
C37 C42 . 1.39
C38 C39 . 1.39
C39 C40 . 1.39
C40 C41 . 1.39
C41 C42 . 1.39
O3 S1 . 1.509(2)
O4 S1 . 1.417(3)
O5 S1 . 1.424(2)
