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#$Date: 2016-03-22 12:43:07 +0200 (Tue, 22 Mar 2016) $
#$Revision: 178960 $
#$URL: svn://www.crystallography.net/cod/cif/4/11/89/4118995.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_4118995
loop_
_publ_author_name
'Holger Braunschweig'
'Alexander Damme'
'J. Oscar C. Jimenez-Halla'
'Christian Hörl'
'Ivo Krummenacher'
'Thomas Kupfer'
'Lisa Mailänder'
'Krzysztof Radacki'
_publ_section_title
;
 1-Heteroaromatic-Substituted Tetraphenylboroles: π-π Interactions
 Between Aromatic and Antiaromatic Rings Through a B-C Bond
;
_journal_name_full               'Journal of the American Chemical Society'
_journal_page_first              20169
_journal_page_last               20177
_journal_paper_doi               10.1021/ja309935t
_journal_volume                  134
_journal_year                    2012
_chemical_formula_moiety         'C33 H26 B N'
_chemical_formula_sum            'C33 H26 B N'
_chemical_formula_weight         447.36
_chemical_name_common
;
?
;
_chemical_name_systematic
; 
?
;
_space_group_IT_number           96
_symmetry_cell_setting           tetragonal
_symmetry_space_group_name_Hall  'P 4nw 2abw'
_symmetry_space_group_name_H-M   'P 43 21 2'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   9.9150(6)
_cell_length_b                   9.9150(6)
_cell_length_c                   25.0921(15)
_cell_measurement_reflns_used    8095
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      25.80
_cell_measurement_theta_min      2.21
_cell_volume                     2466.7(3)
_computing_cell_refinement       'Saint+ ver. 7.68A (Bruker AXS)'
_computing_data_collection       'APEX2 ver. 2010.3 (Bruker AXS)'
_computing_data_reduction        'Saint+ ver. 7.68A (Bruker AXS)'
_computing_molecular_graphics    'XP ver. 5.1 (Bruker AXS, 1998)'
_computing_publication_material  'SHELXL-97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      293(2)
_diffrn_detector_area_resol_mean 8.333
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_device_type  'Bruker X8-APEX II'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_monochromator  'multi-layer mirror'
_diffrn_radiation_source         'rotating anode'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0691
_diffrn_reflns_av_sigmaI/netI    0.0258
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_limit_l_min       -31
_diffrn_reflns_number            26171
_diffrn_reflns_theta_full        26.00
_diffrn_reflns_theta_max         26.42
_diffrn_reflns_theta_min         2.21
_exptl_absorpt_coefficient_mu    0.068
_exptl_absorpt_correction_T_max  0.7454
_exptl_absorpt_correction_T_min  0.5810
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'Sadabs 2008/1 (Bruker 2008)'
_exptl_crystal_colour            red
_exptl_crystal_density_diffrn    1.205
_exptl_crystal_description       plate
_exptl_crystal_F_000             944
_exptl_crystal_size_max          0.26
_exptl_crystal_size_mid          0.14
_exptl_crystal_size_min          0.06
_refine_diff_density_max         0.156
_refine_diff_density_min         -0.138
_refine_diff_density_rms         0.030
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.139
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     187
_refine_ls_number_reflns         1543
_refine_ls_number_restraints     88
_refine_ls_restrained_S_all      1.129
_refine_ls_R_factor_all          0.0511
_refine_ls_R_factor_gt           0.0397
_refine_ls_shift/su_max          0.029
_refine_ls_shift/su_mean         0.002
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0295P)²+0.8095P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0913
_refine_ls_wR_factor_ref         0.0958
_reflns_number_gt                1296
_reflns_number_total             1543
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ja309935t_si_001_4.cif
_cod_data_source_block           11
_cod_database_code               4118995
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, z+1/2'
'-y+1/2, x+1/2, z+3/4'
'y+1/2, -x+1/2, z+1/4'
'-x+1/2, y+1/2, -z+3/4'
'x+1/2, -y+1/2, -z+1/4'
'y, x, -z'
'-y, -x, -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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
B1_1 B 0.6411(3) 0.6411(3) 0.0000 0.0323(8) Uani 1 2 d S . .
C2_1 C 0.6400(2) 0.7820(2) 0.02934(8) 0.0319(5) Uani 1 1 d . A .
C3_1 C 0.7590(2) 0.8440(2) 0.01866(8) 0.0316(5) Uani 1 1 d . . .
C1_2 C 0.5344(2) 0.8369(2) 0.06500(9) 0.0328(5) Uani 1 1 d . . .
C2_2 C 0.4090(3) 0.8706(3) 0.04443(10) 0.0449(6) Uani 1 1 d . A .
H2_2 H 0.3929 0.8595 0.0082 0.054 Uiso 1 1 calc R . .
C3_2 C 0.3081(3) 0.9200(3) 0.07659(11) 0.0485(7) Uani 1 1 d . . .
H3_2 H 0.2254 0.9439 0.0618 0.058 Uiso 1 1 calc R A .
C4_2 C 0.3289(3) 0.9342(3) 0.13005(11) 0.0473(7) Uani 1 1 d . A .
H4_2 H 0.2597 0.9650 0.1519 0.057 Uiso 1 1 calc R . .
C5_2 C 0.4529(3) 0.9025(3) 0.15141(10) 0.0460(7) Uani 1 1 d . . .
H5_2 H 0.4678 0.9135 0.1877 0.055 Uiso 1 1 calc R A .
C6_2 C 0.5552(3) 0.8545(2) 0.11930(9) 0.0380(6) Uani 1 1 d . A .
H6_2 H 0.6387 0.8339 0.1341 0.046 Uiso 1 1 calc R . .
C1_3 C 0.8054(2) 0.9736(2) 0.04164(9) 0.0327(5) Uani 1 1 d . A .
C2_3 C 0.7220(3) 1.0868(2) 0.04307(9) 0.0361(6) Uani 1 1 d . . .
H2_3 H 0.6363 1.0828 0.0280 0.043 Uiso 1 1 calc R A .
C3_3 C 0.7656(3) 1.2045(3) 0.06664(9) 0.0410(6) Uani 1 1 d . A .
H3_3 H 0.7097 1.2798 0.0668 0.049 Uiso 1 1 calc R . .
C4_3 C 0.8906(3) 1.2121(3) 0.08991(10) 0.0462(7) Uani 1 1 d . . .
H4_3 H 0.9190 1.2916 0.1061 0.055 Uiso 1 1 calc R A .
C5_3 C 0.9737(3) 1.1005(3) 0.08910(10) 0.0484(7) Uani 1 1 d . A .
H5_3 H 1.0584 1.1048 0.1050 0.058 Uiso 1 1 calc R . .
C6_3 C 0.9321(2) 0.9824(3) 0.06489(10) 0.0404(6) Uani 1 1 d . . .
H6_3 H 0.9895 0.9082 0.0642 0.048 Uiso 1 1 calc R A .
C1_4 C 0.5372(19) 0.530(2) -0.0010(11) 0.0368(14) Uani 0.50 1 d PDU A -1
C2_4 C 0.5215(12) 0.4187(14) -0.0256(4) 0.0433(17) Uani 0.50 1 d PDU A -1
H2_4 H 0.5843 0.3865 -0.0500 0.052 Uiso 0.50 1 calc PR A -1
N3_4 N 0.4064(7) 0.3502(9) -0.0137(3) 0.0434(15) Uani 0.50 1 d PDU A -1
C4_4 C 0.3384(11) 0.4276(10) 0.0237(3) 0.0444(16) Uani 0.50 1 d PDU A -1
H4_4 H 0.2561 0.4051 0.0391 0.053 Uiso 0.50 1 calc PR A -1
C5_4 C 0.4074(14) 0.5375(12) 0.0342(4) 0.0430(16) Uani 0.50 1 d PDU A -1
H5_4 H 0.3839 0.6059 0.0578 0.052 Uiso 0.50 1 calc PR A -1
C6_4 C 0.3658(6) 0.2231(6) -0.0360(2) 0.0523(14) Uani 0.50 1 d PDU A -1
H6A_4 H 0.3709 0.1544 -0.0091 0.078 Uiso 0.50 1 calc PR A -1
H6B_4 H 0.4247 0.2001 -0.0650 0.078 Uiso 0.50 1 calc PR A -1
H6C_4 H 0.2748 0.2297 -0.0488 0.078 Uiso 0.50 1 calc PR A -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'
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
C2_1 B1_1 C2_1 103.2(3) 7 .
C3_1 C2_1 B1_1 107.6(2) . .
C2_1 C3_1 C3_1 110.71(13) . 7
C2_2 C1_2 C6_2 117.9(2) . .
C3_2 C2_2 C1_2 121.3(2) . .
C3_2 C2_2 H2_2 119.4 . .
C1_2 C2_2 H2_2 119.4 . .
C4_2 C3_2 C2_2 120.2(3) . .
C4_2 C3_2 H3_2 119.9 . .
C2_2 C3_2 H3_2 119.9 . .
C3_2 C4_2 C5_2 119.6(2) . .
C3_2 C4_2 H4_2 120.2 . .
C5_2 C4_2 H4_2 120.2 . .
C4_2 C5_2 C6_2 120.5(2) . .
C4_2 C5_2 H5_2 119.7 . .
C6_2 C5_2 H5_2 119.7 . .
C5_2 C6_2 C1_2 120.4(2) . .
C5_2 C6_2 H6_2 119.8 . .
C1_2 C6_2 H6_2 119.8 . .
C6_3 C1_3 C2_3 118.4(2) . .
C3_3 C2_3 C1_3 120.4(2) . .
C3_3 C2_3 H2_3 119.8 . .
C1_3 C2_3 H2_3 119.8 . .
C4_3 C3_3 C2_3 120.9(2) . .
C4_3 C3_3 H3_3 119.6 . .
C2_3 C3_3 H3_3 119.6 . .
C3_3 C4_3 C5_3 119.3(3) . .
C3_3 C4_3 H4_3 120.3 . .
C5_3 C4_3 H4_3 120.3 . .
C4_3 C5_3 C6_3 120.5(3) . .
C4_3 C5_3 H5_3 119.7 . .
C6_3 C5_3 H5_3 119.7 . .
C5_3 C6_3 C1_3 120.5(2) . .
C5_3 C6_3 H6_3 119.7 . .
C1_3 C6_3 H6_3 119.7 . .
C5_4 C1_4 C2_4 102.4(6) . .
N3_4 C2_4 C1_4 115.4(15) . .
N3_4 C2_4 H2_4 122.3 . .
C1_4 C2_4 H2_4 122.3 . .
C4_4 N3_4 C2_4 106.2(10) . .
C4_4 N3_4 C6_4 127.8(10) . .
C2_4 N3_4 C6_4 125.9(7) . .
C5_4 C4_4 N3_4 110.0(11) . .
C5_4 C4_4 H4_4 125.0 . .
N3_4 C4_4 H4_4 125.0 . .
C4_4 C5_4 C1_4 106.0(12) . .
C4_4 C5_4 H5_4 127.0 . .
C1_4 C5_4 H5_4 127.0 . .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
B1_1 C2_1 1.580(3) 7
B1_1 C2_1 1.580(3) .
C2_1 C3_1 1.357(3) .
C3_1 C3_1 1.516(4) 7
C1_2 C2_2 1.386(3) .
C1_2 C6_2 1.389(3) .
C2_2 C3_2 1.376(4) .
C2_2 H2_2 0.9300 .
C3_2 C4_2 1.364(4) .
C3_2 H3_2 0.9300 .
C4_2 C5_2 1.378(4) .
C4_2 H4_2 0.9300 .
C5_2 C6_2 1.380(3) .
C5_2 H5_2 0.9300 .
C6_2 H6_2 0.9300 .
C1_3 C6_3 1.388(3) .
C1_3 C2_3 1.394(3) .
C2_3 C3_3 1.379(3) .
C2_3 H2_3 0.9300 .
C3_3 C4_3 1.372(4) .
C3_3 H3_3 0.9300 .
C4_3 C5_3 1.380(4) .
C4_3 H4_3 0.9300 .
C5_3 C6_3 1.383(3) .
C5_3 H5_3 0.9300 .
C6_3 H6_3 0.9300 .
C1_4 C5_4 1.56(4) .
C1_4 C2_4 1.27(3) .
C2_4 N3_4 1.362(14) .
C2_4 H2_4 0.9300 .
N3_4 C4_4 1.387(7) .
N3_4 C6_4 1.437(10) .
C4_4 C5_4 1.313(16) .
C4_4 H4_4 0.9300 .
C5_4 H5_4 0.9300 .
C6_4 H6A_4 0.9600 .
C6_4 H6B_4 0.9600 .
C6_4 H6C_4 0.9600 .
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_4
C2_1 B1_1 C2_1 C3_1 -0.98(11) 7 .
B1_1 C2_1 C3_1 C3_1 2.4(3) . 7
C6_2 C1_2 C2_2 C3_2 0.0(4) . .
C1_2 C2_2 C3_2 C4_2 -1.4(4) . .
C2_2 C3_2 C4_2 C5_2 1.9(4) . .
C3_2 C4_2 C5_2 C6_2 -1.1(4) . .
C4_2 C5_2 C6_2 C1_2 -0.4(4) . .
C2_2 C1_2 C6_2 C5_2 0.9(4) . .
C6_3 C1_3 C2_3 C3_3 0.6(4) . .
C1_3 C2_3 C3_3 C4_3 -1.2(4) . .
C2_3 C3_3 C4_3 C5_3 0.7(4) . .
C3_3 C4_3 C5_3 C6_3 0.3(4) . .
C4_3 C5_3 C6_3 C1_3 -0.9(4) . .
C2_3 C1_3 C6_3 C5_3 0.4(4) . .
C5_4 C1_4 C2_4 N3_4 -0.01(5) . .
C1_4 C2_4 N3_4 C4_4 -0.04(6) . .
C1_4 C2_4 N3_4 C6_4 179.99(7) . .
C2_4 N3_4 C4_4 C5_4 0.08(11) . .
C6_4 N3_4 C4_4 C5_4 -179.95(10) . .
N3_4 C4_4 C5_4 C1_4 -0.08(13) . .
C2_4 C1_4 C5_4 C4_4 0.05(10) . .
