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#$Date: 2020-06-17 01:46:17 +0300 (Wed, 17 Jun 2020) $
#$Revision: 253180 $
#$URL: file:///home/coder/svn-repositories/cod/cif/4/13/50/4135067.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_4135067
loop_
_publ_author_name
'Scholz, Alexander Stefan'
'Massoth, Julian'
'Bursch, Markus'
'Mewes, Jan'
'Hetzke, Thilo'
'Wolf, Bernd'
'Bolte, Michael'
'Lerner, Hans-Wolfram'
'Grimme, Stefan'
'Wagner, Matthias'
_publ_section_title
;
 BNB-Doped Phenalenyls: Modular Synthesis, Optoelectronic Properties, and
 One-Electron Reduction.
;
_journal_name_full               'Journal of the American Chemical Society'
_journal_paper_doi               10.1021/jacs.0c03118
_journal_year                    2020
_chemical_formula_moiety         'C10 H10 B2'
_chemical_formula_sum            'C10 H10 B2'
_chemical_formula_weight         151.80
_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   mixed
_atom_sites_solution_primary     direct
_audit_creation_method           SHELXL-2016/6
_cell_angle_alpha                91.182(6)
_cell_angle_beta                 103.436(6)
_cell_angle_gamma                97.147(6)
_cell_formula_units_Z            4
_cell_length_a                   7.0969(5)
_cell_length_b                   8.5411(6)
_cell_length_c                   14.8555(11)
_cell_measurement_reflns_used    19290
_cell_measurement_temperature    173(2)
_cell_measurement_theta_max      29.85
_cell_measurement_theta_min      3.57
_cell_volume                     867.87(11)
_computing_cell_refinement       'X-Area (Stoe & Cie, 2001)'
_computing_data_collection       'X-Area (Stoe & Cie, 2001)'
_computing_data_reduction        'X-Area (Stoe & Cie, 2001)'
_computing_molecular_graphics    'XP in SHELXTL-Plus (Sheldrick, 2008)'
_computing_publication_material  SHELXL
_computing_structure_refinement  'SHELXL (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS (Sheldrick, 2008)'
_diffrn_ambient_temperature      173(2)
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.994
_diffrn_measurement_device_type  'STOE IPDS II two-circle-diffractometer'
_diffrn_measurement_method       ω
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0267
_diffrn_reflns_av_unetI/netI     0.0210
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.994
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_number            19290
_diffrn_reflns_point_group_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.994
_diffrn_reflns_theta_full        25.000
_diffrn_reflns_theta_max         29.581
_diffrn_reflns_theta_min         3.572
_diffrn_source                   'Genix 3D I\mS microfocus X-ray source'
_exptl_absorpt_coefficient_mu    0.062
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_correction_T_min  0.526
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'X-Area (Stoe & Cie, 2001)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.162
_exptl_crystal_description       block
_exptl_crystal_F_000             320
_exptl_crystal_size_max          0.290
_exptl_crystal_size_mid          0.290
_exptl_crystal_size_min          0.270
_refine_diff_density_max         0.286
_refine_diff_density_min         -0.198
_refine_diff_density_rms         0.043
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.056
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     249
_refine_ls_number_reflns         4841
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.056
_refine_ls_R_factor_all          0.0547
_refine_ls_R_factor_gt           0.0475
_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)+(0.0778P)²+0.1381P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1302
_refine_ls_wR_factor_ref         0.1351
_reflns_Friedel_coverage         0.000
_reflns_number_gt                4197
_reflns_number_total             4841
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            ja0c03118_si_021.cif
_cod_data_source_block           wa2446
_cod_database_code               4135067
_shelx_shelxl_version_number     2016/6
_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. 
;
_shelx_estimated_absorpt_t_min   0.982
_shelx_estimated_absorpt_t_max   0.983
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
B1 B 0.69452(16) 0.67094(14) 0.60327(7) 0.0279(2) Uani 1 1 d . . . . .
B2 B 0.75057(17) 0.85243(13) 0.67226(8) 0.0283(2) Uani 1 1 d . . . . .
H1 H 0.591(2) 0.7768(16) 0.6222(9) 0.036(3) Uiso 1 1 d . . . . .
H2 H 0.847(2) 0.7797(16) 0.6259(9) 0.037(3) Uiso 1 1 d . . . . .
H1B H 0.657(2) 0.6481(16) 0.5278(10) 0.039(4) Uiso 1 1 d . . . . .
H2B H 0.762(2) 0.9743(17) 0.6519(10) 0.042(4) Uiso 1 1 d . . . . .
C1 C 0.70994(13) 0.54602(11) 0.68021(6) 0.02325(18) Uani 1 1 d . . . . .
C2 C 0.75986(12) 0.62221(10) 0.77051(6) 0.02170(18) Uani 1 1 d . . . . .
C3 C 0.78485(13) 0.79089(11) 0.77308(6) 0.02415(19) Uani 1 1 d . . . . .
C4 C 0.83157(15) 0.87122(12) 0.85841(7) 0.0310(2) Uani 1 1 d . . . . .
H4 H 0.849523 0.983468 0.862026 0.037 Uiso 1 1 calc R U . . .
C5 C 0.85305(16) 0.78743(14) 0.94092(7) 0.0348(2) Uani 1 1 d . . . . .
H5 H 0.884926 0.844722 0.999132 0.042 Uiso 1 1 calc R U . . .
C6 C 0.82870(15) 0.62516(14) 0.93833(7) 0.0322(2) Uani 1 1 d . . . . .
H6 H 0.843571 0.571755 0.994506 0.039 Uiso 1 1 calc R U . . .
C7 C 0.78129(13) 0.53642(11) 0.85196(6) 0.02512(19) Uani 1 1 d . . . . .
C8 C 0.75294(15) 0.36881(12) 0.84119(7) 0.0308(2) Uani 1 1 d . . . . .
H8 H 0.767385 0.307493 0.894405 0.037 Uiso 1 1 calc R U . . .
C9 C 0.70471(15) 0.29472(12) 0.75426(8) 0.0320(2) Uani 1 1 d . . . . .
H9 H 0.685983 0.182558 0.748399 0.038 Uiso 1 1 calc R U . . .
C10 C 0.68236(14) 0.38221(12) 0.67320(7) 0.0286(2) Uani 1 1 d . . . . .
H10 H 0.648370 0.328405 0.613893 0.034 Uiso 1 1 calc R U . . .
B1A B 0.26599(16) 0.50488(13) 0.80812(8) 0.0276(2) Uani 1 1 d . . . . .
B2A B 0.20387(16) 0.46241(12) 0.68540(8) 0.0263(2) Uani 1 1 d . . . . .
H1A H 0.1057(19) 0.4523(16) 0.7500(9) 0.034(3) Uiso 1 1 d . . . . .
H2A H 0.360(2) 0.4595(16) 0.7470(9) 0.036(3) Uiso 1 1 d . . . . .
H1C H 0.286(2) 0.4227(16) 0.8657(9) 0.037(3) Uiso 1 1 d . . . . .
H2C H 0.1691(18) 0.3493(15) 0.6445(9) 0.029(3) Uiso 1 1 d . . . . .
C1A C 0.28873(13) 0.69082(12) 0.81331(6) 0.02485(19) Uani 1 1 d . . . . .
C2A C 0.25391(12) 0.75033(10) 0.72256(6) 0.02215(18) Uani 1 1 d . . . . .
C3A C 0.20713(13) 0.63361(10) 0.64813(6) 0.02240(18) Uani 1 1 d . . . . .
C4A C 0.17347(14) 0.68341(12) 0.55835(7) 0.0278(2) Uani 1 1 d . . . . .
H4A H 0.142120 0.607774 0.507552 0.033 Uiso 1 1 calc R U . . .
C5A C 0.18565(16) 0.84700(13) 0.54198(7) 0.0336(2) Uani 1 1 d . . . . .
H5A H 0.162455 0.879532 0.480036 0.040 Uiso 1 1 calc R U . . .
C6A C 0.23036(15) 0.95943(12) 0.61399(8) 0.0337(2) Uani 1 1 d . . . . .
H6A H 0.238123 1.068282 0.601263 0.040 Uiso 1 1 calc R U . . .
C7A C 0.26509(14) 0.91398(11) 0.70745(7) 0.0276(2) Uani 1 1 d . . . . .
C8A C 0.30949(16) 1.01972(12) 0.78721(9) 0.0364(2) Uani 1 1 d . . . . .
H8A H 0.316148 1.130383 0.779981 0.044 Uiso 1 1 calc R U . . .
C9A C 0.34275(17) 0.96260(14) 0.87454(9) 0.0395(3) Uani 1 1 d . . . . .
H9A H 0.372502 1.034833 0.926939 0.047 Uiso 1 1 calc R U . . .
C10A C 0.33364(15) 0.79814(14) 0.88816(7) 0.0336(2) Uani 1 1 d . . . . .
H10A H 0.358667 0.761793 0.949274 0.040 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'
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
C1 B1 B2 101.32(7) . . ?
C1 B1 H1 108.8(6) . . ?
B2 B1 H1 46.1(6) . . ?
C1 B1 H2 108.9(6) . . ?
B2 B1 H2 45.6(6) . . ?
H1 B1 H2 87.5(8) . . ?
C1 B1 H1B 127.7(7) . . ?
B2 B1 H1B 131.0(7) . . ?
H1 B1 H1B 107.7(9) . . ?
H2 B1 H1B 108.9(9) . . ?
C3 B2 B1 101.54(7) . . ?
C3 B2 H1 108.9(6) . . ?
B1 B2 H1 46.6(6) . . ?
C3 B2 H2 109.2(6) . . ?
B1 B2 H2 47.0(6) . . ?
H1 B2 H2 89.3(8) . . ?
C3 B2 H2B 127.9(8) . . ?
B1 B2 H2B 130.5(8) . . ?
H1 B2 H2B 108.3(10) . . ?
H2 B2 H2B 106.4(10) . . ?
C10 C1 C2 118.12(8) . . ?
C10 C1 B1 130.95(9) . . ?
C2 C1 B1 110.92(8) . . ?
C7 C2 C1 122.25(8) . . ?
C7 C2 C3 122.30(8) . . ?
C1 C2 C3 115.44(8) . . ?
C4 C3 C2 118.12(9) . . ?
C4 C3 B2 131.10(9) . . ?
C2 C3 B2 110.77(8) . . ?
C3 C4 C5 120.46(9) . . ?
C3 C4 H4 119.8 . . ?
C5 C4 H4 119.8 . . ?
C6 C5 C4 121.35(9) . . ?
C6 C5 H5 119.3 . . ?
C4 C5 H5 119.3 . . ?
C5 C6 C7 120.45(9) . . ?
C5 C6 H6 119.8 . . ?
C7 C6 H6 119.8 . . ?
C2 C7 C8 117.51(8) . . ?
C2 C7 C6 117.31(9) . . ?
C8 C7 C6 125.17(9) . . ?
C9 C8 C7 120.47(9) . . ?
C9 C8 H8 119.8 . . ?
C7 C8 H8 119.8 . . ?
C8 C9 C10 121.41(9) . . ?
C8 C9 H9 119.3 . . ?
C10 C9 H9 119.3 . . ?
C1 C10 C9 120.23(9) . . ?
C1 C10 H10 119.9 . . ?
C9 C10 H10 119.9 . . ?
C1A B1A B2A 101.38(7) . . ?
C1A B1A H1A 108.7(6) . . ?
B2A B1A H1A 46.9(6) . . ?
C1A B1A H2A 108.2(6) . . ?
H1A B1A H2A 88.0(8) . . ?
C1A B1A H1C 129.0(7) . . ?
B2A B1A H1C 129.7(7) . . ?
H1A B1A H1C 107.3(9) . . ?
H2A B1A H1C 108.0(9) . . ?
C3A B2A B1A 101.33(7) . . ?
C3A B2A H1A 109.0(6) . . ?
B1A B2A H1A 45.6(6) . . ?
C3A B2A H2A 107.8(6) . . ?
B1A B2A H2A 47.6(6) . . ?
H1A B2A H2A 89.2(8) . . ?
C3A B2A H2C 127.6(7) . . ?
B1A B2A H2C 131.1(7) . . ?
H1A B2A H2C 107.8(9) . . ?
H2A B2A H2C 108.7(9) . . ?
C10A C1A C2A 118.07(9) . . ?
C10A C1A B1A 131.09(9) . . ?
C2A C1A B1A 110.84(8) . . ?
C7A C2A C3A 122.17(8) . . ?
C7A C2A C1A 122.43(9) . . ?
C3A C2A C1A 115.40(8) . . ?
C4A C3A C2A 118.33(8) . . ?
C4A C3A B2A 130.62(9) . . ?
C2A C3A B2A 111.05(8) . . ?
C3A C4A C5A 120.23(9) . . ?
C3A C4A H4A 119.9 . . ?
C5A C4A H4A 119.9 . . ?
C6A C5A C4A 121.31(9) . . ?
C6A C5A H5A 119.3 . . ?
C4A C5A H5A 119.3 . . ?
C5A C6A C7A 120.52(9) . . ?
C5A C6A H6A 119.7 . . ?
C7A C6A H6A 119.7 . . ?
C2A C7A C6A 117.43(9) . . ?
C2A C7A C8A 117.20(9) . . ?
C6A C7A C8A 125.36(9) . . ?
C9A C8A C7A 120.41(10) . . ?
C9A C8A H8A 119.8 . . ?
C7A C8A H8A 119.8 . . ?
C8A C9A C10A 121.46(10) . . ?
C8A C9A H9A 119.3 . . ?
C10A C9A H9A 119.3 . . ?
C1A C10A C9A 120.42(10) . . ?
C1A C10A H10A 119.8 . . ?
C9A C10A H10A 119.8 . . ?
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
B1 C1 1.5741(14) . ?
B1 B2 1.7897(17) . ?
B1 H1 1.301(14) . ?
B1 H2 1.310(14) . ?
B1 H1B 1.099(14) . ?
B2 C3 1.5728(14) . ?
B2 H1 1.290(14) . ?
B2 H2 1.280(13) . ?
B2 H2B 1.089(15) . ?
C1 C10 1.3867(13) . ?
C1 C2 1.4263(12) . ?
C2 C7 1.4153(12) . ?
C2 C3 1.4282(12) . ?
C3 C4 1.3783(13) . ?
C4 C5 1.4192(15) . ?
C4 H4 0.9500 . ?
C5 C6 1.3738(16) . ?
C5 H5 0.9500 . ?
C6 C7 1.4246(13) . ?
C6 H6 0.9500 . ?
C7 C8 1.4211(14) . ?
C8 C9 1.3756(15) . ?
C8 H8 0.9500 . ?
C9 C10 1.4183(15) . ?
C9 H9 0.9500 . ?
C10 H10 0.9500 . ?
B1A C1A 1.5747(15) . ?
B1A B2A 1.7914(16) . ?
B1A H1A 1.281(13) . ?
B1A H2A 1.323(13) . ?
B1A H1C 1.113(14) . ?
B2A C3A 1.5736(14) . ?
B2A H1A 1.309(13) . ?
B2A H2A 1.267(14) . ?
B2A H2C 1.100(12) . ?
C1A C10A 1.3779(13) . ?
C1A C2A 1.4288(12) . ?
C2A C7A 1.4156(12) . ?
C2A C3A 1.4242(12) . ?
C3A C4A 1.3847(12) . ?
C4A C5A 1.4187(15) . ?
C4A H4A 0.9500 . ?
C5A C6A 1.3753(16) . ?
C5A H5A 0.9500 . ?
C6A C7A 1.4233(15) . ?
C6A H6A 0.9500 . ?
C7A C8A 1.4249(14) . ?
C8A C9A 1.3745(18) . ?
C8A H8A 0.9500 . ?
C9A C10A 1.4190(17) . ?
C9A H9A 0.9500 . ?
C10A H10A 0.9500 . ?
loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C1 B1 B2 C3 -0.17(9) . . . . ?
B2 B1 C1 C10 179.62(10) . . . . ?
B2 B1 C1 C2 0.07(9) . . . . ?
C10 C1 C2 C7 -0.13(13) . . . . ?
B1 C1 C2 C7 179.48(8) . . . . ?
C10 C1 C2 C3 -179.55(8) . . . . ?
B1 C1 C2 C3 0.07(11) . . . . ?
C7 C2 C3 C4 0.05(14) . . . . ?
C1 C2 C3 C4 179.46(8) . . . . ?
C7 C2 C3 B2 -179.61(8) . . . . ?
C1 C2 C3 B2 -0.20(11) . . . . ?
B1 B2 C3 C4 -179.38(10) . . . . ?
B1 B2 C3 C2 0.22(10) . . . . ?
C2 C3 C4 C5 -0.27(14) . . . . ?
B2 C3 C4 C5 179.31(10) . . . . ?
C3 C4 C5 C6 0.18(16) . . . . ?
C4 C5 C6 C7 0.14(16) . . . . ?
C1 C2 C7 C8 0.58(13) . . . . ?
C3 C2 C7 C8 179.95(8) . . . . ?
C1 C2 C7 C6 -179.11(8) . . . . ?
C3 C2 C7 C6 0.26(13) . . . . ?
C5 C6 C7 C2 -0.35(14) . . . . ?
C5 C6 C7 C8 179.98(10) . . . . ?
C2 C7 C8 C9 -0.59(14) . . . . ?
C6 C7 C8 C9 179.08(9) . . . . ?
C7 C8 C9 C10 0.17(15) . . . . ?
C2 C1 C10 C9 -0.32(14) . . . . ?
B1 C1 C10 C9 -179.84(9) . . . . ?
C8 C9 C10 C1 0.31(15) . . . . ?
C1A B1A B2A C3A 0.53(9) . . . . ?
B2A B1A C1A C10A 179.27(10) . . . . ?
B2A B1A C1A C2A -0.36(10) . . . . ?
C10A C1A C2A C7A 0.36(14) . . . . ?
B1A C1A C2A C7A -179.96(8) . . . . ?
C10A C1A C2A C3A -179.66(8) . . . . ?
B1A C1A C2A C3A 0.03(11) . . . . ?
C7A C2A C3A C4A 0.58(13) . . . . ?
C1A C2A C3A C4A -179.40(8) . . . . ?
C7A C2A C3A B2A -179.63(8) . . . . ?
C1A C2A C3A B2A 0.39(11) . . . . ?
B1A B2A C3A C4A 179.20(9) . . . . ?
B1A B2A C3A C2A -0.56(9) . . . . ?
C2A C3A C4A C5A -0.05(14) . . . . ?
B2A C3A C4A C5A -179.79(9) . . . . ?
C3A C4A C5A C6A -0.12(15) . . . . ?
C4A C5A C6A C7A -0.23(16) . . . . ?
C3A C2A C7A C6A -0.91(14) . . . . ?
C1A C2A C7A C6A 179.07(8) . . . . ?
C3A C2A C7A C8A 178.85(8) . . . . ?
C1A C2A C7A C8A -1.17(14) . . . . ?
C5A C6A C7A C2A 0.72(15) . . . . ?
C5A C6A C7A C8A -179.01(10) . . . . ?
C2A C7A C8A C9A 1.06(15) . . . . ?
C6A C7A C8A C9A -179.21(10) . . . . ?
C7A C8A C9A C10A -0.16(17) . . . . ?
C2A C1A C10A C9A 0.59(15) . . . . ?
B1A C1A C10A C9A -179.02(10) . . . . ?
C8A C9A C10A C1A -0.70(17) . . . . ?
