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#$Date: 2024-08-05 20:30:16 +0300 (Mon, 05 Aug 2024) $
#$Revision: 293703 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/13/32/7133272.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_7133272
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            'C34 H43 B2 N3'
_chemical_formula_weight         515.33
_chemical_properties_physical    Air-sensitive,Moisture-sensitive
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2yn'
_space_group_name_H-M_alt        'P 1 21/n 1'
_atom_sites_solution_hydrogens   mixed
_audit_creation_method           SHELXL-2014/7
_audit_update_record
;
2024-02-07 deposited with the CCDC.	2024-07-01 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 104.319(2)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   11.6929(6)
_cell_length_b                   17.5821(9)
_cell_length_c                   14.6284(8)
_cell_measurement_reflns_used    9817
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      30.65
_cell_measurement_theta_min      2.32
_cell_volume                     2914.0(3)
_computing_cell_refinement       'Bruker SAINT'
_computing_data_collection       'Bruker APEX2'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_structure_solution    'SHELXS-97 (Sheldrick 2008)'
_diffrn_ambient_temperature      100(2)
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.992
_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  0.0676
_diffrn_reflns_av_unetI/netI     0.0650
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.992
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_k_max       25
_diffrn_reflns_limit_k_min       -24
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_number            44958
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.992
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         30.680
_diffrn_reflns_theta_min         1.845
_exptl_absorpt_coefficient_mu    0.067
_exptl_absorpt_correction_T_max  0.7461
_exptl_absorpt_correction_T_min  0.6936
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   sadabs
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.175
_exptl_crystal_description       needle
_exptl_crystal_F_000             1112
_exptl_crystal_recrystallization_method
'Re-crystallisation from solvent: Hexane'
_exptl_crystal_size_max          0.200
_exptl_crystal_size_mid          0.120
_exptl_crystal_size_min          0.070
_refine_diff_density_max         0.362
_refine_diff_density_min         -0.259
_refine_diff_density_rms         0.055
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.009
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     361
_refine_ls_number_reflns         8946
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.009
_refine_ls_R_factor_all          0.1012
_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)+(0.0584P)²+1.0051P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1201
_refine_ls_wR_factor_ref         0.1389
_reflns_Friedel_coverage         0.000
_reflns_number_gt                5786
_reflns_number_total             8946
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d4cc02414a2.cif
_cod_data_source_block           vpn041_a
_cod_depositor_comments
'Adding full bibliography for 7133270--7133276.cif.'
_cod_original_sg_symbol_H-M      'P 21/n'
_cod_database_code               7133272
_shelx_shelxl_version_number     2014/7
_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+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_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
N1_1 N 0.82547(10) 0.61997(7) 0.71625(8) 0.0142(2) Uani 1 1 d . . . . .
C1_1 C 0.82469(13) 0.64410(9) 0.89954(10) 0.0171(3) Uani 1 1 d . . . . .
H1A_1 H 0.8945 0.6768 0.9082 0.020 Uiso 1 1 calc R U . . .
B1_1 B 0.75137(14) 0.64750(10) 0.78891(11) 0.0137(3) Uani 1 1 d . . . . .
N2_1 N 0.85045(10) 0.58723(7) 0.57842(8) 0.0145(2) Uani 1 1 d . . . . .
C2_1 C 0.86530(14) 0.56186(10) 0.92879(11) 0.0223(3) Uani 1 1 d . . . . .
H2A_1 H 0.9247 0.5474 0.8960 0.027 Uiso 1 1 calc R U . . .
H2B_1 H 0.9027 0.5615 0.9958 0.027 Uiso 1 1 calc R U . . .
B2_1 B 0.65604(14) 0.66867(10) 0.57518(11) 0.0146(3) Uani 1 1 d . . . . .
H1_1 H 0.5771(15) 0.6309(10) 0.5639(12) 0.022 Uiso 1 1 d . U . . .
N3_1 N 0.63926(10) 0.73165(7) 0.65147(8) 0.0145(2) Uani 1 1 d . . . . .
C3_1 C 0.76797(15) 0.50150(9) 0.90903(11) 0.0230(3) Uani 1 1 d . . . . .
H3A_1 H 0.7239 0.5050 0.9570 0.028 Uiso 1 1 calc R U . . .
H3B_1 H 0.8043 0.4516 0.9141 0.028 Uiso 1 1 calc R U . . .
C4_1 C 0.68147(15) 0.50882(9) 0.81139(11) 0.0210(3) Uani 1 1 d . . . . .
H4A_1 H 0.6131 0.4773 0.8103 0.025 Uiso 1 1 calc R U . . .
H4B_1 H 0.7193 0.4889 0.7644 0.025 Uiso 1 1 calc R U . . .
C5_1 C 0.63889(13) 0.59025(9) 0.78293(10) 0.0158(3) Uani 1 1 d . . . . .
H5_1 H 0.5924 0.5890 0.7173 0.019 Uiso 1 1 calc R U . . .
C6_1 C 0.93592(13) 0.58676(9) 0.72995(10) 0.0178(3) Uani 1 1 d . . . . .
H6_1 H 0.9902 0.5803 0.7877 0.021 Uiso 1 1 calc R U . . .
C7_1 C 0.95138(13) 0.56531(9) 0.64496(10) 0.0179(3) Uani 1 1 d . . . . .
H7_1 H 1.0168 0.5407 0.6335 0.022 Uiso 1 1 calc R U . . .
C8_1 C 0.77518(12) 0.62201(8) 0.62318(10) 0.0131(3) Uani 1 1 d . . . . .
C9_1 C 0.69736(12) 0.72948(9) 0.74525(10) 0.0135(3) Uani 1 1 d . . . . .
C10_1 C 0.74828(15) 0.67207(9) 0.96605(11) 0.0213(3) Uani 1 1 d . . . . .
H10A_1 H 0.7900 0.6605 1.0305 0.026 Uiso 1 1 calc R U . . .
H10B_1 H 0.7413 0.7270 0.9607 0.026 Uiso 1 1 calc R U . . .
C11_1 C 0.62298(14) 0.63810(10) 0.94796(11) 0.0216(3) Uani 1 1 d . . . . .
H11A_1 H 0.6277 0.5903 0.9818 0.026 Uiso 1 1 calc R U . . .
H11B_1 H 0.5745 0.6723 0.9743 0.026 Uiso 1 1 calc R U . . .
C12_1 C 0.56058(13) 0.62361(10) 0.84378(10) 0.0188(3) Uani 1 1 d . . . . .
H12A_1 H 0.5277 0.6713 0.8158 0.023 Uiso 1 1 calc R U . . .
H12B_1 H 0.4952 0.5891 0.8414 0.023 Uiso 1 1 calc R U . . .
C13_1 C 0.82583(13) 0.57027(8) 0.47887(10) 0.0142(3) Uani 1 1 d . . . . .
C14_1 C 0.88894(12) 0.60775(8) 0.42271(10) 0.0152(3) Uani 1 1 d . . . . .
C15_1 C 0.85544(13) 0.59434(9) 0.32580(10) 0.0172(3) Uani 1 1 d . . . . .
H15_1 H 0.8944 0.6201 0.2868 0.021 Uiso 1 1 calc R U . . .
C16_1 C 0.76548(13) 0.54365(9) 0.28540(10) 0.0185(3) Uani 1 1 d . . . . .
C17_1 C 0.71021(13) 0.50418(9) 0.34492(10) 0.0174(3) Uani 1 1 d . . . . .
H17_1 H 0.6522 0.4687 0.3191 0.021 Uiso 1 1 calc R U . . .
C18_1 C 0.73912(13) 0.51623(9) 0.44194(10) 0.0155(3) Uani 1 1 d . . . . .
C19_1 C 0.66885(12) 0.71173(9) 0.47967(10) 0.0140(3) Uani 1 1 d . . . . .
C20_1 C 0.59411(12) 0.69316(9) 0.39064(10) 0.0151(3) Uani 1 1 d . . . . .
C21_1 C 0.61379(13) 0.72489(9) 0.30789(10) 0.0184(3) Uani 1 1 d . . . . .
H21_1 H 0.5645 0.7111 0.2501 0.022 Uiso 1 1 calc R U . . .
C22_1 C 0.70437(14) 0.77610(9) 0.30969(11) 0.0197(3) Uani 1 1 d . . . . .
C23_1 C 0.77361(13) 0.79784(9) 0.39769(11) 0.0191(3) Uani 1 1 d . . . . .
H23_1 H 0.8323 0.8341 0.4007 0.023 Uiso 1 1 calc R U . . .
C24_1 C 0.75747(13) 0.76673(9) 0.48144(10) 0.0151(3) Uani 1 1 d . . . . .
C25_1 C 0.56986(13) 0.79142(9) 0.61530(11) 0.0188(3) Uani 1 1 d . . . . .
H25_1 H 0.5277 0.7896 0.5525 0.023 Uiso 1 1 calc R U . . .
C26_1 C 0.55921(14) 0.85447(9) 0.66743(11) 0.0206(3) Uani 1 1 d . . . . .
H26_1 H 0.5075 0.8935 0.6418 0.025 Uiso 1 1 calc R U . . .
C27_1 C 0.62772(14) 0.85865(9) 0.75953(11) 0.0201(3) Uani 1 1 d . . . . .
H27_1 H 0.6284 0.9025 0.7953 0.024 Uiso 1 1 calc R U . . .
C28_1 C 0.69475(13) 0.79629(9) 0.79677(10) 0.0164(3) Uani 1 1 d . . . . .
H28_1 H 0.7401 0.7987 0.8586 0.020 Uiso 1 1 calc R U . . .
C29_1 C 0.99144(13) 0.65984(10) 0.46346(11) 0.0208(3) Uani 1 1 d . . . . .
H29A_1 H 1.0015 0.6951 0.4159 0.031 Uiso 1 1 calc R U . . .
H29B_1 H 1.0620 0.6302 0.4846 0.031 Uiso 1 1 calc R U . . .
H29C_1 H 0.9760 0.6874 0.5158 0.031 Uiso 1 1 calc R U . . .
C30_1 C 0.73005(17) 0.53157(12) 0.18030(12) 0.0331(4) Uani 1 1 d . . . . .
H30A_1 H 0.6480 0.5437 0.1567 0.050 Uiso 1 1 calc R U . . .
H30B_1 H 0.7431 0.4794 0.1664 0.050 Uiso 1 1 calc R U . . .
H30C_1 H 0.7765 0.5639 0.1507 0.050 Uiso 1 1 calc R U . . .
C31_1 C 0.67768(14) 0.47155(10) 0.50389(11) 0.0215(3) Uani 1 1 d . . . . .
H31A_1 H 0.6276 0.4339 0.4667 0.032 Uiso 1 1 calc R U . . .
H31B_1 H 0.6309 0.5054 0.5313 0.032 Uiso 1 1 calc R U . . .
H31C_1 H 0.7355 0.4470 0.5532 0.032 Uiso 1 1 calc R U . . .
C32_1 C 0.49120(13) 0.63921(9) 0.37970(11) 0.0196(3) Uani 1 1 d . . . . .
H32A_1 H 0.4456 0.6397 0.3154 0.029 Uiso 1 1 calc R U . . .
H32B_1 H 0.4424 0.6549 0.4203 0.029 Uiso 1 1 calc R U . . .
H32C_1 H 0.5201 0.5887 0.3965 0.029 Uiso 1 1 calc R U . . .
C33_1 C 0.72791(16) 0.80592(11) 0.21929(12) 0.0289(4) Uani 1 1 d . . . . .
H33A_1 H 0.6872 0.7749 0.1674 0.043 Uiso 1 1 calc R U . . .
H33B_1 H 0.8112 0.8044 0.2237 0.043 Uiso 1 1 calc R U . . .
H33C_1 H 0.7003 0.8574 0.2093 0.043 Uiso 1 1 calc R U . . .
C34_1 C 0.83859(13) 0.79460(9) 0.57311(11) 0.0188(3) Uani 1 1 d . . . . .
H34A_1 H 0.9042 0.8213 0.5597 0.028 Uiso 1 1 calc R U . . .
H34B_1 H 0.8670 0.7519 0.6132 0.028 Uiso 1 1 calc R U . . .
H34C_1 H 0.7958 0.8282 0.6043 0.028 Uiso 1 1 calc R U . . .
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
C8_1 N1_1 C6_1 108.44(12) . . ?
C8_1 N1_1 B1_1 119.41(12) . . ?
C6_1 N1_1 B1_1 131.95(12) . . ?
C2_1 C1_1 C10_1 107.87(13) . . ?
C2_1 C1_1 B1_1 110.95(12) . . ?
C10_1 C1_1 B1_1 111.49(12) . . ?
N1_1 B1_1 C1_1 114.10(12) . . ?
N1_1 B1_1 C9_1 103.10(11) . . ?
C1_1 B1_1 C9_1 118.38(12) . . ?
N1_1 B1_1 C5_1 109.68(12) . . ?
C1_1 B1_1 C5_1 104.33(12) . . ?
C9_1 B1_1 C5_1 106.99(12) . . ?
C8_1 N2_1 C7_1 109.01(12) . . ?
C8_1 N2_1 C13_1 125.81(12) . . ?
C7_1 N2_1 C13_1 125.01(12) . . ?
C3_1 C2_1 C1_1 115.61(13) . . ?
N3_1 B2_1 C8_1 106.60(11) . . ?
N3_1 B2_1 C19_1 109.04(12) . . ?
C8_1 B2_1 C19_1 110.84(12) . . ?
C25_1 N3_1 C9_1 120.88(13) . . ?
C25_1 N3_1 B2_1 115.16(12) . . ?
C9_1 N3_1 B2_1 123.77(12) . . ?
C2_1 C3_1 C4_1 113.89(13) . . ?
C3_1 C4_1 C5_1 115.06(13) . . ?
C4_1 C5_1 C12_1 113.35(12) . . ?
C4_1 C5_1 B1_1 110.78(12) . . ?
C12_1 C5_1 B1_1 108.56(12) . . ?
C7_1 C6_1 N1_1 108.42(13) . . ?
C6_1 C7_1 N2_1 106.48(13) . . ?
N1_1 C8_1 N2_1 107.56(12) . . ?
N1_1 C8_1 B2_1 124.53(12) . . ?
N2_1 C8_1 B2_1 127.35(12) . . ?
N3_1 C9_1 C28_1 116.32(13) . . ?
N3_1 C9_1 B1_1 117.50(12) . . ?
C28_1 C9_1 B1_1 125.86(12) . . ?
C11_1 C10_1 C1_1 116.01(13) . . ?
C12_1 C11_1 C10_1 115.54(13) . . ?
C11_1 C12_1 C5_1 115.52(12) . . ?
C18_1 C13_1 C14_1 122.10(13) . . ?
C18_1 C13_1 N2_1 118.37(12) . . ?
C14_1 C13_1 N2_1 119.53(13) . . ?
C15_1 C14_1 C13_1 117.49(13) . . ?
C15_1 C14_1 C29_1 120.01(13) . . ?
C13_1 C14_1 C29_1 122.49(13) . . ?
C16_1 C15_1 C14_1 122.14(13) . . ?
C17_1 C16_1 C15_1 118.19(14) . . ?
C17_1 C16_1 C30_1 121.05(14) . . ?
C15_1 C16_1 C30_1 120.77(14) . . ?
C16_1 C17_1 C18_1 121.94(14) . . ?
C17_1 C18_1 C13_1 117.91(13) . . ?
C17_1 C18_1 C31_1 120.12(14) . . ?
C13_1 C18_1 C31_1 121.98(13) . . ?
C24_1 C19_1 C20_1 117.25(13) . . ?
C24_1 C19_1 B2_1 121.68(12) . . ?
C20_1 C19_1 B2_1 121.02(13) . . ?
C21_1 C20_1 C19_1 120.44(14) . . ?
C21_1 C20_1 C32_1 117.07(13) . . ?
C19_1 C20_1 C32_1 122.49(13) . . ?
C22_1 C21_1 C20_1 122.00(14) . . ?
C21_1 C22_1 C23_1 117.55(14) . . ?
C21_1 C22_1 C33_1 120.87(15) . . ?
C23_1 C22_1 C33_1 121.57(15) . . ?
C22_1 C23_1 C24_1 121.94(14) . . ?
C23_1 C24_1 C19_1 120.64(13) . . ?
C23_1 C24_1 C34_1 117.23(13) . . ?
C19_1 C24_1 C34_1 122.13(13) . . ?
N3_1 C25_1 C26_1 122.67(14) . . ?
C25_1 C26_1 C27_1 118.25(14) . . ?
C28_1 C27_1 C26_1 118.44(15) . . ?
C27_1 C28_1 C9_1 122.71(14) . . ?
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
N1_1 C8_1 1.3434(17) . ?
N1_1 C6_1 1.3860(19) . ?
N1_1 B1_1 1.603(2) . ?
C1_1 C2_1 1.549(2) . ?
C1_1 C10_1 1.554(2) . ?
C1_1 B1_1 1.634(2) . ?
B1_1 C9_1 1.638(2) . ?
B1_1 C5_1 1.641(2) . ?
N2_1 C8_1 1.3646(18) . ?
N2_1 C7_1 1.3859(18) . ?
N2_1 C13_1 1.4439(18) . ?
C2_1 C3_1 1.530(2) . ?
B2_1 N3_1 1.618(2) . ?
B2_1 C8_1 1.620(2) . ?
B2_1 C19_1 1.628(2) . ?
N3_1 C25_1 1.3529(19) . ?
N3_1 C9_1 1.3725(18) . ?
C3_1 C4_1 1.538(2) . ?
C4_1 C5_1 1.539(2) . ?
C5_1 C12_1 1.542(2) . ?
C6_1 C7_1 1.353(2) . ?
C9_1 C28_1 1.400(2) . ?
C10_1 C11_1 1.543(2) . ?
C11_1 C12_1 1.539(2) . ?
C13_1 C18_1 1.397(2) . ?
C13_1 C14_1 1.398(2) . ?
C14_1 C15_1 1.394(2) . ?
C14_1 C29_1 1.509(2) . ?
C15_1 C16_1 1.394(2) . ?
C16_1 C17_1 1.391(2) . ?
C16_1 C30_1 1.505(2) . ?
C17_1 C18_1 1.391(2) . ?
C18_1 C31_1 1.509(2) . ?
C19_1 C24_1 1.413(2) . ?
C19_1 C20_1 1.415(2) . ?
C20_1 C21_1 1.403(2) . ?
C20_1 C32_1 1.509(2) . ?
C21_1 C22_1 1.385(2) . ?
C22_1 C23_1 1.394(2) . ?
C22_1 C33_1 1.510(2) . ?
C23_1 C24_1 1.397(2) . ?
C24_1 C34_1 1.519(2) . ?
C25_1 C26_1 1.368(2) . ?
C26_1 C27_1 1.389(2) . ?
C27_1 C28_1 1.379(2) . ?
