#------------------------------------------------------------------------------
#$Date: 2017-11-28 10:33:13 +0200 (Tue, 28 Nov 2017) $
#$Revision: 203694 $
#$URL: file:///home/coder/svn-repositories/cod/cif/1/54/82/1548261.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_1548261
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            'C35 H32 B2 F2 N4 P'
_chemical_formula_weight         599.23
_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   mixed
_cell_angle_alpha                106.603(3)
_cell_angle_beta                 102.639(3)
_cell_angle_gamma                104.799(3)
_cell_formula_units_Z            2
_cell_length_a                   8.1150(8)
_cell_length_b                   13.1620(13)
_cell_length_c                   16.2320(16)
_cell_measurement_reflns_used    2642
_cell_measurement_temperature    103.(2)
_cell_measurement_theta_max      21.8827
_cell_measurement_theta_min      2.5627
_cell_volume                     1524.6(3)
_computing_cell_refinement       'SAINT V8.34A (Bruker AXS Inc., 2013)'
_computing_data_collection       'APEX3 (Bruker AXS Inc., 2015)'
_computing_data_reduction        'SAINT V8.34A (Bruker AXS Inc., 2013)'
_computing_molecular_graphics    'XP (Bruker AXS Inc., 2015)'
_computing_publication_material  'APEX3 (Bruker AXS Inc., 2015)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_structure_solution    'XT, VERSION 2014/4'
_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  0.1015
_diffrn_reflns_av_unetI/netI     0.1120
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       19
_diffrn_reflns_limit_k_min       -19
_diffrn_reflns_limit_l_max       24
_diffrn_reflns_limit_l_min       -24
_diffrn_reflns_number            43901
_diffrn_reflns_theta_full        32.05
_diffrn_reflns_theta_max         32.05
_diffrn_reflns_theta_min         1.72
_diffrn_source                   'fine-focus sealed tube'
_diffrn_source_type              'Bruker KappaCCD'
_exptl_absorpt_coefficient_mu    0.135
_exptl_absorpt_correction_T_max  0.96
_exptl_absorpt_correction_T_min  0.84
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
SADABS-2014/5 - Bruker AXS area detector scaling and absorption correction
;
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.305
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             626
_exptl_crystal_size_max          0.400
_exptl_crystal_size_mid          0.320
_exptl_crystal_size_min          0.280
_refine_diff_density_max         0.416
_refine_diff_density_min         -0.391
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.037
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     403
_refine_ls_number_reflns         10572
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.037
_refine_ls_R_factor_all          0.1264
_refine_ls_R_factor_gt           0.0635
_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)+(0.0477P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1222
_refine_ls_wR_factor_ref         0.1462
_reflns_number_gt                5984
_reflns_number_total             10572
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            ncomms11871-s7.cif
_cod_data_source_block           V
_cod_depositor_comments
;
The following automatic conversions were performed:

'_exptl_absorpt_correction_type' value 'Multi-Scan' changed to
'multi-scan' according to the built-in table from CIF Core dictionary
named 'cif_core.dic' version 2.4.1 from 2010-06-29.

Automatic conversion script
Id: cif_fix_values 5376 2017-05-30 11:51:03Z andrius 
;
_cod_database_code               1548261
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 0.0103(3) 0.41655(17) 0.28680(14) 0.0167(4) Uani d . . . 1 . .
H H1B 0.036(2) 0.3550(16) 0.3206(13) 0.024(5) Uiso d . . . 1 . .
B B2 0.2750(3) 0.67798(17) 0.38484(14) 0.0165(4) Uani d . . . 1 . .
C C1 -0.2880(3) 0.24833(16) 0.18440(14) 0.0257(4) Uani d . . . 1 . .
H H1 -0.272 0.217 0.2303 0.031 Uiso calc U . R 1 . .
C C2 -0.4373(3) 0.19085(17) 0.10648(15) 0.0312(5) Uani d . . . 1 . .
H H2 -0.5212 0.1216 0.1001 0.037 Uiso calc U . R 1 . .
C C3 -0.4629(3) 0.23474(17) 0.03870(14) 0.0273(5) Uani d . . . 1 . .
H H3 -0.5635 0.1954 -0.0146 0.033 Uiso calc U . R 1 . .
C C4 -0.3416(2) 0.33596(17) 0.04899(13) 0.0251(4) Uani d . . . 1 . .
H H4 -0.3589 0.367 0.003 0.03 Uiso calc U . R 1 . .
C C5 -0.1936(2) 0.39254(16) 0.12707(12) 0.0204(4) Uani d . . . 1 . .
H H5 -0.1114 0.4622 0.1332 0.025 Uiso calc U . R 1 . .
C C6 -0.1615(2) 0.35054(15) 0.19680(12) 0.0179(4) Uani d . . . 1 . .
C C7 -0.1643(3) 0.49596(18) 0.39003(13) 0.0261(4) Uani d . . . 1 . .
H H7 -0.2587 0.4265 0.3725 0.031 Uiso calc U . R 1 . .
C C8 -0.1452(3) 0.59438(18) 0.45225(14) 0.0271(5) Uani d . . . 1 . .
H H8 -0.223 0.6072 0.4871 0.033 Uiso calc U . R 1 . .
C C9 0.0790(3) 0.78902(17) 0.52124(14) 0.0306(5) Uani d . . . 1 . .
H H9A 0.1704 0.7947 0.5747 0.046 Uiso calc U . R 1 . .
H H9B -0.0186 0.8101 0.5395 0.046 Uiso calc U . R 1 . .
H H9C 0.1332 0.8399 0.4932 0.046 Uiso calc U . R 1 . .
C C10 0.0844(2) 0.62297(15) 0.39696(12) 0.0169(4) Uani d . . . 1 . .
C C11 0.1933(2) 0.47450(14) 0.26992(11) 0.0145(3) Uani d . . . 1 . .
C C12 0.1955(3) 0.30186(15) 0.15462(13) 0.0231(4) Uani d . . . 1 . .
H H12A 0.1018 0.2613 0.1742 0.035 Uiso calc U . R 1 . .
H H12B 0.2901 0.268 0.1566 0.035 Uiso calc U . R 1 . .
H H12C 0.1433 0.2969 0.0926 0.035 Uiso calc U . R 1 . .
C C13 0.4382(2) 0.49245(16) 0.22527(12) 0.0194(4) Uani d . . . 1 . .
H H13 0.521 0.4754 0.195 0.023 Uiso calc U . R 1 . .
C C14 0.4594(2) 0.59219(16) 0.28697(12) 0.0195(4) Uani d . . . 1 . .
H H14 0.5613 0.6587 0.3083 0.023 Uiso calc U . R 1 . .
C C15 0.4297(2) 0.72462(15) 0.48214(12) 0.0162(4) Uani d . . . 1 . .
C C16 0.5223(2) 0.83850(16) 0.53678(13) 0.0220(4) Uani d . . . 1 . .
H H16 0.4956 0.8948 0.516 0.026 Uiso calc U . R 1 . .
C C17 0.6513(3) 0.87170(16) 0.62002(13) 0.0246(4) Uani d . . . 1 . .
H H17 0.7144 0.9496 0.654 0.03 Uiso calc U . R 1 . .
C C18 0.6885(3) 0.79169(16) 0.65372(13) 0.0239(4) Uani d . . . 1 . .
H H18 0.777 0.8141 0.7106 0.029 Uiso calc U . R 1 . .
C C19 0.5944(2) 0.67814(16) 0.60300(13) 0.0204(4) Uani d . . . 1 . .
H H19 0.6159 0.6224 0.6261 0.024 Uiso calc U . R 1 . .
C C20 0.4690(2) 0.64598(15) 0.51860(12) 0.0170(4) Uani d . . . 1 . .
H H20 0.4079 0.5679 0.4845 0.02 Uiso calc U . R 1 . .
C C21 0.0823(2) 0.72669(15) 0.22709(12) 0.0178(4) Uani d . . . 1 . .
C C22 -0.0971(3) 0.71511(16) 0.22134(13) 0.0238(4) Uani d . . . 1 . .
H H22 -0.1248 0.7446 0.2752 0.029 Uiso calc U . R 1 . .
C C23 -0.2352(3) 0.66207(18) 0.13958(14) 0.0275(5) Uani d . . . 1 . .
H H23 -0.3562 0.6534 0.1371 0.033 Uiso calc U . R 1 . .
C C24 -0.1912(3) 0.62249(16) 0.06246(13) 0.0233(4) Uani d . . . 1 . .
C C25 -0.0183(3) 0.63073(15) 0.06331(13) 0.0215(4) Uani d . . . 1 . .
H H25 0.0077 0.6025 0.0087 0.026 Uiso calc U . R 1 . .
C C26 0.1172(2) 0.68151(15) 0.14620(13) 0.0194(4) Uani d . . . 1 . .
H H26 0.2367 0.6857 0.1481 0.023 Uiso calc U . R 1 . .
C C27 0.4548(2) 0.86262(15) 0.31046(12) 0.0201(4) Uani d . . . 1 . .
C C28 0.4401(3) 0.90774(16) 0.24147(13) 0.0250(4) Uani d . . . 1 . .
H H28 0.3242 0.8994 0.206 0.03 Uiso calc U . R 1 . .
C C29 0.5900(3) 0.96414(16) 0.22357(14) 0.0287(5) Uani d . . . 1 . .
H H29 0.5773 0.9931 0.1761 0.034 Uiso calc U . R 1 . .
C C30 0.7576(3) 0.97704(16) 0.27620(14) 0.0280(5) Uani d . . . 1 . .
C C31 0.7806(3) 0.93603(16) 0.34488(14) 0.0261(4) Uani d . . . 1 . .
H H31 0.8976 0.9465 0.3805 0.031 Uiso calc U . R 1 . .
C C32 0.6292(3) 0.87872(15) 0.36140(13) 0.0233(4) Uani d . . . 1 . .
H H32 0.6445 0.8496 0.4087 0.028 Uiso calc U . R 1 . .
C C33 0.1061(3) 0.93514(18) 0.01422(16) 0.0364(5) Uani d . . . 1 . .
H H33 0.179 0.8909 0.0239 0.044 Uiso calc U . R 1 . .
C C34 0.0006(3) 0.95778(19) 0.06932(16) 0.0380(6) Uani d . . . 1 . .
H H34 0.0007 0.9289 0.1167 0.046 Uiso calc U . R 1 . .
C C35 -0.1045(3) 1.02282(19) 0.05465(16) 0.0380(6) Uani d . . . 1 . .
H H35 -0.1763 1.0387 0.0924 0.046 Uiso calc U . R 1 . .
F F1 -0.32484(15) 0.57072(10) -0.01873(8) 0.0338(3) Uani d . . . 1 . .
F F2 0.90459(16) 1.03295(11) 0.25951(9) 0.0434(4) Uani d . . . 1 . .
N N1 -0.02187(19) 0.51398(12) 0.35603(10) 0.0176(3) Uani d . . . 1 . .
N N2 0.0077(2) 0.67309(13) 0.45618(11) 0.0218(3) Uani d . . . 1 . .
N N3 0.30700(19) 0.58144(12) 0.31421(10) 0.0152(3) Uani d . . . 1 . .
N N4 0.27198(19) 0.41992(12) 0.21479(10) 0.0165(3) Uani d . . . 1 . .
P P1 0.25270(7) 0.80359(4) 0.33902(3) 0.01870(12) 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'
F F 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
P P 0.1023 0.0942 '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 C11 . . 105.65(14)
N1 B1 C6 . . 111.37(15)
C11 B1 C6 . . 114.90(15)
N3 B2 C10 . . 106.68(14)
N3 B2 C15 . . 110.69(15)
C10 B2 C15 . . 108.46(14)
N3 B2 P1 . . 112.04(12)
C10 B2 P1 . . 106.59(12)
C15 B2 P1 . . 112.09(12)
C6 C1 C2 . . 121.97(19)
C3 C2 C1 . . 120.00(18)
C4 C3 C2 . . 119.61(18)
C3 C4 C5 . . 119.81(19)
C4 C5 C6 . . 122.44(17)
C1 C6 C5 . . 116.16(17)
C1 C6 B1 . . 121.78(17)
C5 C6 B1 . . 122.06(16)
C8 C7 N1 . . 107.68(17)
C7 C8 N2 . . 107.29(17)
N1 C10 N2 . . 106.48(15)
N1 C10 B2 . . 125.82(15)
N2 C10 B2 . . 127.41(16)
N3 C11 N4 . . 107.10(15)
N3 C11 B1 . . 127.16(15)
N4 C11 B1 . . 125.35(15)
C14 C13 N4 . . 106.30(16)
C13 C14 N3 . . 108.52(16)
C20 C15 C16 . . 115.96(16)
C20 C15 B2 . . 118.17(15)
C16 C15 B2 . . 125.75(16)
C17 C16 C15 . . 122.32(17)
C18 C17 C16 . . 120.22(18)
C17 C18 C19 . . 119.03(18)
C20 C19 C18 . . 120.14(17)
C19 C20 C15 . . 122.26(17)
C26 C21 C22 . . 117.07(17)
C26 C21 P1 . . 125.31(14)
C22 C21 P1 . . 117.58(14)
C23 C22 C21 . . 122.16(18)
C24 C23 C22 . . 117.84(18)
F1 C24 C23 . . 118.78(17)
F1 C24 C25 . . 118.23(17)
C23 C24 C25 . . 122.98(18)
C24 C25 C26 . . 118.19(18)
C25 C26 C21 . . 121.71(17)
C32 C27 C28 . . 116.54(17)
C32 C27 P1 . . 123.44(14)
C28 C27 P1 . . 119.51(14)
C29 C28 C27 . . 122.02(19)
C30 C29 C28 . . 118.48(19)
F2 C30 C31 . . 119.04(19)
F2 C30 C29 . . 118.73(19)
C31 C30 C29 . . 122.23(19)
C30 C31 C32 . . 118.64(19)
C31 C32 C27 . . 122.08(18)
C35 C33 C34 2_575 . 119.8(2)
C35 C34 C33 . . 119.5(2)
C33 C35 C34 2_575 . 120.7(2)
C10 N1 C7 . . 109.18(15)
C10 N1 B1 . . 127.90(15)
C7 N1 B1 . . 122.74(15)
C10 N2 C8 . . 109.37(16)
C10 N2 C9 . . 127.39(16)
C8 N2 C9 . . 123.02(17)
C11 N3 C14 . . 108.29(14)
C11 N3 B2 . . 126.37(14)
C14 N3 B2 . . 125.34(15)
C11 N4 C13 . . 109.78(15)
C11 N4 C12 . . 125.55(15)
C13 N4 C12 . . 124.66(15)
C21 P1 C27 . . 102.50(8)
C21 P1 B2 . . 102.59(8)
C27 P1 B2 . . 110.48(9)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_site_symmetry_2
_geom_bond_distance
B1 N1 . 1.566(3)
B1 C11 . 1.607(3)
B1 C6 . 1.612(3)
B2 N3 . 1.569(2)
B2 C10 . 1.612(3)
B2 C15 . 1.622(3)
B2 P1 . 2.029(2)
C1 C6 . 1.398(2)
C1 C2 . 1.398(3)
C2 C3 . 1.383(3)
C3 C4 . 1.380(3)
C4 C5 . 1.393(2)
C5 C6 . 1.399(2)
C7 C8 . 1.343(3)
C7 N1 . 1.382(2)
C8 N2 . 1.374(2)
C9 N2 . 1.463(2)
C10 N1 . 1.347(2)
C10 N2 . 1.363(2)
C11 N3 . 1.348(2)
C11 N4 . 1.357(2)
C12 N4 . 1.459(2)
C13 C14 . 1.347(3)
C13 N4 . 1.381(2)
C14 N3 . 1.389(2)
C15 C20 . 1.400(2)
C15 C16 . 1.404(2)
C16 C17 . 1.387(3)
C17 C18 . 1.385(3)
C18 C19 . 1.390(3)
C19 C20 . 1.389(2)
C21 C26 . 1.400(3)
C21 C22 . 1.404(2)
C21 P1 . 1.8361(18)
C22 C23 . 1.387(3)
C23 C24 . 1.372(3)
C24 F1 . 1.364(2)
C24 C25 . 1.376(3)
C25 C26 . 1.389(2)
C27 C32 . 1.402(3)
C27 C28 . 1.407(3)
C27 P1 . 1.8430(19)
C28 C29 . 1.390(3)
C29 C30 . 1.378(3)
C30 F2 . 1.358(2)
C30 C31 . 1.369(3)
C31 C32 . 1.392(3)
C33 C35 2_575 1.381(3)
C33 C34 . 1.390(3)
C34 C35 . 1.385(3)
C35 C33 2_575 1.381(3)
