#------------------------------------------------------------------------------
#$Date: 2024-08-05 20:30:16 +0300 (Mon, 05 Aug 2024) $
#$Revision: 293703 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/13/32/7133271.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_7133271
loop_
_publ_author_name
'Pattathil, Vignesh'
'Pranckevicius, Conor'
_publ_section_title
;
 Aromaticity transfer in an annulated 1,4,2-diazaborole: facile access to
 Cₛ symmetric 1,4,2,5-diazadiborinines.
;
_journal_issue                   60
_journal_name_full               'Chemical communications (Cambridge, England)'
_journal_page_first              7705
_journal_page_last               7708
_journal_paper_doi               10.1039/d4cc02414a
_journal_volume                  60
_journal_year                    2024
_chemical_formula_sum            'C32 H33 B2 N3'
_chemical_formula_weight         481.23
_chemical_properties_physical
Air-sensitive,Moisture-sensitive,Oxygen-sensitive
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_atom_sites_solution_hydrogens   geom
_audit_creation_method           SHELXL-2019/1
_audit_update_record
;
2024-02-07 deposited with the CCDC.	2024-07-01 downloaded from the CCDC.
;
_cell_angle_alpha                105.413(2)
_cell_angle_beta                 90.951(2)
_cell_angle_gamma                109.556(2)
_cell_formula_units_Z            2
_cell_length_a                   8.9434(6)
_cell_length_b                   12.0020(8)
_cell_length_c                   13.5298(9)
_cell_measurement_reflns_used    9900
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      55.93
_cell_measurement_theta_min      4.866
_cell_volume                     1310.34(15)
_computing_cell_refinement       'SAINT V8.40B (Bruker AXS LLC, 2019)'
_computing_data_collection       'Bruker Instrument Service v8.5.0.27 Release'
_computing_data_reduction        'SAINT V8.40B (Bruker AXS LLC, 2019)'
_computing_molecular_graphics    'shelXle (C.B. Huebschle, rev 1503)'
_computing_publication_material  'shelXle (C.B. Huebschle, rev 1503)'
_computing_structure_refinement  'SHELXL-2019/1 (Sheldrick, 2019)'
_computing_structure_solution    'XT, VERSION 2018/2'
_diffrn_ambient_temperature      100(2)
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.994
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0503
_diffrn_reflns_av_unetI/netI     0.0483
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.994
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            31471
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.994
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         26.731
_diffrn_reflns_theta_min         2.075
_exptl_absorpt_coefficient_mu    0.070
_exptl_absorpt_correction_T_max  0.7457
_exptl_absorpt_correction_T_min  0.6877
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   sadabs
_exptl_crystal_colour            red
_exptl_crystal_density_diffrn    1.220
_exptl_crystal_description       plate
_exptl_crystal_F_000             512
_exptl_crystal_recrystallization_method
'Re-crystallisation from solvent: Benzene'
_exptl_crystal_size_max          0.200
_exptl_crystal_size_mid          0.120
_exptl_crystal_size_min          0.070
_refine_diff_density_max         0.277
_refine_diff_density_min         -0.273
_refine_diff_density_rms         0.072
_refine_ls_extinction_coef       0.014(3)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2019/1 (Sheldrick 2019)'
_refine_ls_goodness_of_fit_ref   1.061
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     341
_refine_ls_number_reflns         5543
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.061
_refine_ls_R_factor_all          0.0926
_refine_ls_R_factor_gt           0.0550
_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)+(0.0711P)²+0.8173P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1285
_refine_ls_wR_factor_ref         0.1619
_reflns_Friedel_coverage         0.000
_reflns_number_gt                3871
_reflns_number_total             5543
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d4cc02414a2.cif
_cod_data_source_block           diazadiborinine_a
_cod_depositor_comments
'Adding full bibliography for 7133270--7133276.cif.'
_cod_database_code               7133271
_shelx_shelxl_version_number     2019/1
_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.
;
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'
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
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
N001 N 0.64269(19) 0.79886(14) 0.59953(12) 0.0190(4) Uani 1 1 d . . . . .
N002 N 0.30363(18) 0.73842(14) 0.57593(12) 0.0188(4) Uani 1 1 d . . . . .
N003 N 0.26888(19) 0.68706(15) 0.40538(12) 0.0212(4) Uani 1 1 d . . . . .
C004 C 0.5605(2) 0.81137(17) 0.68993(14) 0.0196(4) Uani 1 1 d . . . . .
C005 C 0.3842(2) 0.72763(17) 0.48907(14) 0.0189(4) Uani 1 1 d . . . . .
C006 C 0.6588(2) 0.74080(17) 0.39855(14) 0.0194(4) Uani 1 1 d . . . . .
C007 C 0.2966(2) 0.67797(18) 0.29965(14) 0.0200(4) Uani 1 1 d . . . . .
C008 C 0.2864(2) 0.80219(18) 0.77547(15) 0.0205(4) Uani 1 1 d . . . . .
C009 C 0.8093(2) 0.82997(17) 0.61475(15) 0.0215(4) Uani 1 1 d . . . . .
H009 H 0.865430 0.823408 0.555720 0.026 Uiso 1 1 calc R U . . .
C00A C 0.1539(2) 0.70955(19) 0.79260(15) 0.0230(4) Uani 1 1 d . . . . .
H00A H 0.117417 0.630231 0.743527 0.028 Uiso 1 1 calc R U . . .
C00B C 0.3287(2) 0.57560(18) 0.23951(15) 0.0214(4) Uani 1 1 d . . . . .
C00C C 0.7033(2) 0.63613(18) 0.36339(15) 0.0202(4) Uani 1 1 d . . . . .
C00D C 0.7698(2) 0.61549(18) 0.27069(15) 0.0222(4) Uani 1 1 d . . . . .
H00D H 0.795379 0.542855 0.246907 0.027 Uiso 1 1 calc R U . . .
C00E C 0.1412(2) 0.70362(18) 0.54377(15) 0.0228(4) Uani 1 1 d . . . . .
H00E H 0.058763 0.701592 0.587370 0.027 Uiso 1 1 calc R U . . .
C00F C 0.8932(2) 0.86845(18) 0.70823(15) 0.0237(5) Uani 1 1 d . . . . .
H00F H 1.005758 0.888585 0.713853 0.028 Uiso 1 1 calc R U . . .
C00G C 0.6954(2) 0.82761(18) 0.34118(15) 0.0212(4) Uani 1 1 d . . . . .
C00H C 0.8142(2) 0.87928(18) 0.79923(15) 0.0238(4) Uani 1 1 d . . . . .
H00H H 0.871938 0.905812 0.865851 0.029 Uiso 1 1 calc R U . . .
C00I C 0.6541(2) 0.85036(18) 0.78704(15) 0.0229(4) Uani 1 1 d . . . . .
H00I H 0.600688 0.856482 0.847277 0.028 Uiso 1 1 calc R U . . .
C00J C 0.7998(2) 0.69836(19) 0.21208(15) 0.0239(5) Uani 1 1 d . . . . .
C00K C 0.3322(2) 0.91868(19) 0.84928(15) 0.0236(4) Uani 1 1 d . . . . .
H00K H 0.421003 0.984320 0.840170 0.028 Uiso 1 1 calc R U . . .
C00L C 0.6822(2) 0.54497(19) 0.42503(16) 0.0237(5) Uani 1 1 d . . . . .
H00B H 0.625071 0.461200 0.380305 0.036 Uiso 1 1 calc R U . . .
H00C H 0.620603 0.564226 0.482240 0.036 Uiso 1 1 calc R U . . .
H00G H 0.787230 0.550304 0.452534 0.036 Uiso 1 1 calc R U . . .
C00M C 0.3267(2) 0.76727(19) 0.15981(15) 0.0235(4) Uani 1 1 d . . . . .
H00M H 0.323019 0.831057 0.131724 0.028 Uiso 1 1 calc R U . . .
C00N C 0.1223(2) 0.67346(19) 0.44005(16) 0.0248(5) Uani 1 1 d . . . . .
H00N H 0.023870 0.647134 0.397830 0.030 Uiso 1 1 calc R U . . .
C00O C 0.3665(2) 0.57560(19) 0.14029(15) 0.0243(5) Uani 1 1 d . . . . .
H00O H 0.391178 0.508049 0.098862 0.029 Uiso 1 1 calc R U . . .
C00P C 0.7640(2) 0.80481(19) 0.24950(15) 0.0246(5) Uani 1 1 d . . . . .
H00P H 0.786798 0.863716 0.211685 0.030 Uiso 1 1 calc R U . . .
C00Q C 0.2891(2) 0.77256(18) 0.25984(15) 0.0207(4) Uani 1 1 d . . . . .
C00R C 0.2515(3) 0.9406(2) 0.93504(16) 0.0275(5) Uani 1 1 d . . . . .
H00R H 0.284437 1.020482 0.983105 0.033 Uiso 1 1 calc R U . . .
C00S C 0.6660(3) 0.94778(19) 0.38009(17) 0.0287(5) Uani 1 1 d . . . . .
H00J H 0.635774 0.972140 0.321313 0.043 Uiso 1 1 calc R U . . .
H00L H 0.763638 1.012046 0.419953 0.043 Uiso 1 1 calc R U . . .
H00Q H 0.579599 0.937128 0.424237 0.043 Uiso 1 1 calc R U . . .
C00T C 0.0739(2) 0.7298(2) 0.87918(16) 0.0266(5) Uani 1 1 d . . . . .
H00T H -0.014059 0.664439 0.889496 0.032 Uiso 1 1 calc R U . . .
C00U C 0.3695(2) 0.67157(19) 0.09937(15) 0.0246(5) Uani 1 1 d . . . . .
C00V C 0.2414(3) 0.87714(19) 0.32177(16) 0.0281(5) Uani 1 1 d . . . . .
H00S H 0.270783 0.944058 0.289121 0.042 Uiso 1 1 calc R U . . .
H00U H 0.296808 0.907779 0.392015 0.042 Uiso 1 1 calc R U . . .
H00V H 0.125732 0.847590 0.324448 0.042 Uiso 1 1 calc R U . . .
C00W C 0.3200(3) 0.46873(19) 0.28012(17) 0.0280(5) Uani 1 1 d . . . . .
H00W H 0.377797 0.420203 0.238466 0.042 Uiso 1 1 calc R U . . .
H00X H 0.208019 0.416395 0.276276 0.042 Uiso 1 1 calc R U . . .
H00Y H 0.368623 0.499962 0.352094 0.042 Uiso 1 1 calc R U . . .
C00X C 0.1231(3) 0.8459(2) 0.95034(16) 0.0284(5) Uani 1 1 d . . . . .
H00Z H 0.068709 0.860282 1.009477 0.034 Uiso 1 1 calc R U . . .
C00Y C 0.8730(3) 0.6745(2) 0.11234(16) 0.0326(5) Uani 1 1 d . . . . .
H010 H 0.819335 0.696079 0.060407 0.049 Uiso 1 1 calc R U . . .
H011 H 0.860178 0.586903 0.087762 0.049 Uiso 1 1 calc R U . . .
H012 H 0.986916 0.724883 0.124140 0.049 Uiso 1 1 calc R U . . .
C00Z C 0.4233(3) 0.6747(2) -0.00490(16) 0.0327(5) Uani 1 1 d . . . . .
H013 H 0.387316 0.590503 -0.051645 0.049 Uiso 1 1 calc R U . . .
H014 H 0.540152 0.710461 0.001876 0.049 Uiso 1 1 calc R U . . .
H015 H 0.377499 0.725144 -0.032869 0.049 Uiso 1 1 calc R U . . .
B1 B 0.5637(3) 0.75725(19) 0.49584(17) 0.0196(5) Uani 1 1 d . . . . .
B2 B 0.3844(3) 0.7824(2) 0.68029(17) 0.0199(5) Uani 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
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C009 N001 C004 117.31(16) . . ?
C009 N001 B1 119.16(16) . . ?
C004 N001 B1 123.52(16) . . ?
C005 N002 C00E 108.39(16) . . ?
C005 N002 B2 122.82(16) . . ?
C00E N002 B2 128.77(16) . . ?
C00N N003 C005 109.22(16) . . ?
C00N N003 C007 123.68(16) . . ?
C005 N003 C007 126.47(16) . . ?
C00I C004 N001 117.07(17) . . ?
C00I C004 B2 122.39(17) . . ?
N001 C004 B2 120.53(17) . . ?
N003 C005 N002 105.90(16) . . ?
N003 C005 B1 131.67(17) . . ?
N002 C005 B1 122.43(17) . . ?
C00C C006 C00G 117.80(17) . . ?
C00C C006 B1 120.96(17) . . ?
C00G C006 B1 121.18(17) . . ?
C00Q C007 C00B 122.04(18) . . ?
C00Q C007 N003 118.19(16) . . ?
C00B C007 N003 119.77(17) . . ?
C00A C008 C00K 116.34(18) . . ?
C00A C008 B2 123.98(18) . . ?
C00K C008 B2 119.68(18) . . ?
C00F C009 N001 123.50(18) . . ?
C00T C00A C008 122.16(19) . . ?
C00O C00B C007 117.54(18) . . ?
C00O C00B C00W 121.14(18) . . ?
C007 C00B C00W 121.31(18) . . ?
C00D C00C C006 120.25(18) . . ?
C00D C00C C00L 118.55(17) . . ?
C006 C00C C00L 121.20(17) . . ?
C00J C00D C00C 121.84(18) . . ?
C00N C00E N002 107.82(17) . . ?
C009 C00F C00H 120.35(19) . . ?
C00P C00G C006 120.27(18) . . ?
C00P C00G C00S 119.14(18) . . ?
C006 C00G C00S 120.56(17) . . ?
C00I C00H C00F 117.48(18) . . ?
C00H C00I C004 124.24(19) . . ?
C00P C00J C00D 117.90(18) . . ?
C00P C00J C00Y 121.20(19) . . ?
C00D C00J C00Y 120.88(19) . . ?
C00R C00K C008 121.99(19) . . ?
C00Q C00M C00U 122.20(19) . . ?
C00E C00N N003 108.66(18) . . ?
C00B C00O C00U 122.25(18) . . ?
C00J C00P C00G 121.76(18) . . ?
C00M C00Q C007 117.77(18) . . ?
C00M C00Q C00V 120.27(18) . . ?
C007 C00Q C00V 121.96(17) . . ?
C00X C00R C00K 119.9(2) . . ?
C00X C00T C00A 119.70(19) . . ?
C00M C00U C00O 117.95(18) . . ?
C00M C00U C00Z 120.65(19) . . ?
C00O C00U C00Z 121.35(18) . . ?
C00R C00X C00T 119.88(19) . . ?
N001 B1 C005 114.43(17) . . ?
N001 B1 C006 121.60(18) . . ?
C005 B1 C006 123.95(17) . . ?
N002 B2 C004 116.22(17) . . ?
N002 B2 C008 119.87(18) . . ?
C004 B2 C008 123.86(18) . . ?
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
N001 C009 1.406(2) . ?
N001 C004 1.437(2) . ?
N001 B1 1.441(3) . ?
N002 C005 1.388(2) . ?
N002 C00E 1.396(3) . ?
N002 B2 1.452(3) . ?
N003 C00N 1.372(3) . ?
N003 C005 1.384(2) . ?
N003 C007 1.438(2) . ?
C004 C00I 1.421(3) . ?
C004 B2 1.490(3) . ?
C005 B1 1.519(3) . ?
C006 C00C 1.409(3) . ?
C006 C00G 1.416(3) . ?
C006 B1 1.584(3) . ?
C007 C00Q 1.399(3) . ?
C007 C00B 1.402(3) . ?
C008 C00A 1.400(3) . ?
C008 C00K 1.407(3) . ?
C008 B2 1.580(3) . ?
C009 C00F 1.342(3) . ?
C00A C00T 1.392(3) . ?
C00B C00O 1.390(3) . ?
C00B C00W 1.504(3) . ?
C00C C00D 1.395(3) . ?
C00C C00L 1.510(3) . ?
C00D C00J 1.392(3) . ?
C00E C00N 1.345(3) . ?
C00F C00H 1.427(3) . ?
C00G C00P 1.395(3) . ?
C00G C00S 1.510(3) . ?
C00H C00I 1.351(3) . ?
C00J C00P 1.388(3) . ?
C00J C00Y 1.510(3) . ?
C00K C00R 1.389(3) . ?
C00M C00Q 1.390(3) . ?
C00M C00U 1.393(3) . ?
C00O C00U 1.397(3) . ?
C00Q C00V 1.507(3) . ?
C00R C00X 1.383(3) . ?
C00T C00X 1.387(3) . ?
C00U C00Z 1.504(3) . ?
