#------------------------------------------------------------------------------
#$Date: 2016-03-21 03:54:20 +0200 (Mon, 21 Mar 2016) $
#$Revision: 178449 $
#$URL: svn://www.crystallography.net/cod/cif/4/02/70/4027007.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_4027007
loop_
_publ_author_name
'Benedikt Neue'
'Roland Fröhlich'
'Birgit Wibbeling'
'Aiko Fukazawa'
'Atsushi Wakamiya'
'Shigehiro Yamaguchi'
'Ernst-Ulrich Würthwein'
_publ_section_title
;
 Synthesis and Photophysical Properties of Aryl-Substituted
 2-Borylbenzaldimines and Their Extended π-Conjugated Congeners
;
_journal_name_full               'Journal of Organic Chemistry'
_journal_page_first              2176
_journal_page_last               2184
_journal_paper_doi               10.1021/jo202212s
_journal_volume                  77
_journal_year                    2012
_chemical_formula_sum            'C62 H64 B2 Cl4 N2'
_chemical_formula_weight         1000.57
_chemical_name_systematic
; 
 ? 
;
_space_group_IT_number           15
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-C 2yc'
_symmetry_space_group_name_H-M   'C 1 2/c 1'
_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                 121.608(2)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   37.6706(14)
_cell_length_b                   8.0291(5)
_cell_length_c                   21.1282(5)
_cell_measurement_reflns_used    5016
_cell_measurement_temperature    223(2)
_cell_measurement_theta_max      68.25
_cell_measurement_theta_min      0.88
_cell_volume                     5442.5(4)
_computing_cell_refinement       'Collect (Nonius B.V., 1998)'
_computing_data_collection       'Collect (Nonius B.V., 1998)'
_computing_data_reduction        'Denzo-SMN (Otwinowski & Minor, 1997)'
_computing_molecular_graphics    'XP (BrukerAXS, 2000)'
_computing_publication_material  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      223(2)
_diffrn_measured_fraction_theta_full 0.980
_diffrn_measured_fraction_theta_max 0.980
_diffrn_measurement_device_type  'Nonius KappaCCD APEXII'
_diffrn_measurement_method       'ω and φ scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.064
_diffrn_reflns_av_sigmaI/netI    0.0234
_diffrn_reflns_limit_h_max       44
_diffrn_reflns_limit_h_min       -43
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_limit_l_min       -24
_diffrn_reflns_number            37677
_diffrn_reflns_theta_full        67.03
_diffrn_reflns_theta_max         67.03
_diffrn_reflns_theta_min         4.19
_exptl_absorpt_coefficient_mu    2.279
_exptl_absorpt_correction_T_max  0.7560
_exptl_absorpt_correction_T_min  0.3954
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
'Denzo (Otwinowski, Borek, Majewski & Minor, 2003)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.221
_exptl_crystal_description       column
_exptl_crystal_F_000             2112
_exptl_crystal_size_max          0.50
_exptl_crystal_size_mid          0.13
_exptl_crystal_size_min          0.13
_refine_diff_density_max         0.621
_refine_diff_density_min         -0.515
_refine_diff_density_rms         0.046
_refine_ls_extinction_coef       0.00099(9)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     SHELXL
_refine_ls_goodness_of_fit_ref   1.041
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     333
_refine_ls_number_reflns         4762
_refine_ls_number_restraints     43
_refine_ls_restrained_S_all      1.136
_refine_ls_R_factor_all          0.0732
_refine_ls_R_factor_gt           0.0612
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0779P)²+8.8578P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1593
_refine_ls_wR_factor_ref         0.1704
_reflns_number_gt                3893
_reflns_number_total             4762
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            jo202212s_si_005.cif
_cod_data_source_block           wue6111
_cod_database_code               4027007
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y, -z+1/2'
'x+1/2, y+1/2, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y, z-1/2'
'-x+1/2, -y+1/2, -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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
N1 N 0.09666(6) 0.8595(2) 0.34428(11) 0.0341(5) Uani 1 1 d . . .
B1 B 0.13661(8) 0.9964(4) 0.38651(15) 0.0342(6) Uani 1 1 d . . .
C1 C 0.16641(7) 0.8730(3) 0.45443(13) 0.0347(5) Uani 1 1 d . . .
C2 C 0.20858(7) 0.8793(4) 0.50854(14) 0.0431(6) Uani 1 1 d . . .
H2 H 0.2247 0.9711 0.5106 0.052 Uiso 1 1 calc R . .
C3 C 0.22701(8) 0.7512(4) 0.55939(14) 0.0507(7) Uani 1 1 d . . .
H3 H 0.2555 0.7581 0.5961 0.061 Uiso 1 1 calc R . .
C4 C 0.20453(9) 0.6132(4) 0.55749(15) 0.0525(7) Uani 1 1 d . . .
H4 H 0.2176 0.5292 0.5935 0.063 Uiso 1 1 calc R . .
C5 C 0.16304(9) 0.5983(4) 0.50314(15) 0.0473(7) Uani 1 1 d . . .
H5 H 0.1475 0.5043 0.5007 0.057 Uiso 1 1 calc R . .
C6 C 0.14491(7) 0.7280(3) 0.45181(13) 0.0373(6) Uani 1 1 d . . .
C7 C 0.10394(7) 0.7316(3) 0.38704(14) 0.0377(6) Uani 1 1 d . . .
H7 H 0.0840 0.6485 0.3763 0.045 Uiso 1 1 calc R . .
C8 C 0.05613(7) 0.8775(3) 0.27816(13) 0.0364(6) Uani 1 1 d . . .
C9 C 0.05270(7) 0.8889(4) 0.21067(14) 0.0442(6) Uani 1 1 d . . .
H9 H 0.0768 0.8896 0.2080 0.053 Uiso 1 1 calc R . .
C10 C 0.01334(8) 0.8996(4) 0.14530(14) 0.0476(7) Uani 1 1 d . . .
H10 H 0.0114 0.9111 0.0993 0.057 Uiso 1 1 calc R . .
C11 C -0.02210(7) 0.8937(3) 0.14750(14) 0.0407(6) Uani 1 1 d . . .
H11 H -0.0482 0.8973 0.1030 0.049 Uiso 1 1 calc R . .
C12 C -0.01986(7) 0.8821(3) 0.21633(13) 0.0342(5) Uani 1 1 d . . .
C21 C 0.16071(7) 1.0348(3) 0.34222(12) 0.0345(5) Uani 1 1 d . . .
C22 C 0.16655(7) 0.9140(3) 0.29955(13) 0.0374(6) Uani 1 1 d . . .
C23 C 0.18841(8) 0.9537(4) 0.26480(14) 0.0478(7) Uani 1 1 d . . .
H23 H 0.1903 0.8734 0.2343 0.057 Uiso 1 1 calc R . .
C24 C 0.20735(9) 1.1060(4) 0.27349(16) 0.0531(8) Uani 1 1 d . . .
C25 C 0.20483(8) 1.2190(4) 0.32024(16) 0.0509(7) Uani 1 1 d . . .
H25 H 0.2187 1.3217 0.3292 0.061 Uiso 1 1 calc R . .
C26 C 0.18257(7) 1.1865(3) 0.35463(14) 0.0408(6) Uani 1 1 d . . .
C27 C 0.15385(9) 0.7334(4) 0.29412(17) 0.0498(7) Uani 1 1 d . . .
H27A H 0.1669 0.6686 0.2730 0.075 Uiso 1 1 calc R . .
H27B H 0.1238 0.7243 0.2626 0.075 Uiso 1 1 calc R . .
H27C H 0.1627 0.6915 0.3433 0.075 Uiso 1 1 calc R . .
C28 C 0.23191(13) 1.1442(6) 0.2366(2) 0.0841(12) Uani 1 1 d . . .
H28A H 0.2614 1.1301 0.2725 0.126 Uiso 1 1 calc R . .
H28B H 0.2266 1.2581 0.2187 0.126 Uiso 1 1 calc R . .
H28C H 0.2234 1.0688 0.1952 0.126 Uiso 1 1 calc R . .
C29 C 0.18453(9) 1.3182(4) 0.40767(18) 0.0537(7) Uani 1 1 d . . .
H29A H 0.2060 1.3988 0.4173 0.081 Uiso 1 1 calc R . .
H29B H 0.1910 1.2660 0.4540 0.081 Uiso 1 1 calc R . .
H29C H 0.1578 1.3742 0.3857 0.081 Uiso 1 1 calc R . .
C31 C 0.11145(7) 1.1449(3) 0.40244(14) 0.0375(6) Uani 1 1 d . . .
C32 C 0.11365(9) 1.1624(3) 0.47166(16) 0.0461(7) Uani 1 1 d . . .
C33 C 0.08392(10) 1.2564(4) 0.47640(19) 0.0555(8) Uani 1 1 d . . .
H33 H 0.0856 1.2617 0.5223 0.067 Uiso 1 1 calc R . .
C34 C 0.05223(9) 1.3415(4) 0.4169(2) 0.0583(8) Uani 1 1 d . . .
C35 C 0.05224(8) 1.3379(4) 0.35186(18) 0.0524(7) Uani 1 1 d . . .
H35 H 0.0321 1.4006 0.3112 0.063 Uiso 1 1 calc R . .
C36 C 0.08100(8) 1.2445(3) 0.34379(15) 0.0430(6) Uani 1 1 d . . .
C37 C 0.14840(12) 1.0924(5) 0.54443(17) 0.0671(9) Uani 1 1 d . . .
H37A H 0.1460 1.1353 0.5849 0.101 Uiso 1 1 calc R . .
H37B H 0.1751 1.1251 0.5517 0.101 Uiso 1 1 calc R . .
H37C H 0.1465 0.9719 0.5434 0.101 Uiso 1 1 calc R . .
C38 C 0.01986(12) 1.4368(5) 0.4240(3) 0.0874(13) Uani 1 1 d . . .
H38A H 0.0039 1.5067 0.3805 0.131 Uiso 1 1 calc R . .
H38B H 0.0336 1.5058 0.4682 0.131 Uiso 1 1 calc R . .
H38C H 0.0014 1.3589 0.4277 0.131 Uiso 1 1 calc R . .
C39 C 0.07793(10) 1.2648(4) 0.26983(16) 0.0563(8) Uani 1 1 d . . .
H39A H 0.0493 1.2473 0.2298 0.084 Uiso 1 1 calc R . .
H39B H 0.0958 1.1838 0.2660 0.084 Uiso 1 1 calc R . .
H39C H 0.0867 1.3763 0.2663 0.084 Uiso 1 1 calc R . .
C100 C 0.1001(7) 0.253(2) 0.1374(10) 0.099(2) Uani 0.250(3) 1 d PDU A 1
H10A H 0.1218 0.1941 0.1815 0.119 Uiso 0.250(3) 1 calc PR A 1
H10B H 0.0819 0.3091 0.1508 0.119 Uiso 0.250(3) 1 calc PR A 1
Cl1 Cl 0.0713(5) 0.1101(15) 0.0681(12) 0.1125(10) Uani 0.250(3) 1 d PDU A 1
Cl2 Cl 0.1229(3) 0.3985(9) 0.1098(4) 0.1465(10) Uani 0.250(3) 1 d PDU A 1
C101 C 0.11546(19) 0.2452(7) 0.1289(4) 0.099(2) Uani 0.750(3) 1 d PDU A 2
H10C H 0.1266 0.1939 0.1779 0.119 Uiso 0.750(3) 1 calc PR A 2
H10D H 0.1353 0.2248 0.1131 0.119 Uiso 0.750(3) 1 calc PR A 2
Cl3 Cl 0.06791(15) 0.1539(4) 0.0658(3) 0.1125(10) Uani 0.750(3) 1 d PDU A 2
Cl4 Cl 0.11040(9) 0.4557(3) 0.13569(13) 0.1465(10) Uani 0.750(3) 1 d PDU A 2
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 '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 0.0090 0.0039 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cl Cl 0.3639 0.7018 '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
C7 N1 C8 119.0(2) . .
C7 N1 B1 109.99(19) . .
C8 N1 B1 130.17(19) . .
C1 B1 C21 106.71(19) . .
C1 B1 C31 117.6(2) . .
C21 B1 C31 121.7(2) . .
C1 B1 N1 94.67(18) . .
C21 B1 N1 115.27(19) . .
C31 B1 N1 97.40(17) . .
C2 C1 C6 116.8(2) . .
C2 C1 B1 132.1(2) . .
C6 C1 B1 110.9(2) . .
C3 C2 C1 120.2(3) . .
C3 C2 H2 119.9 . .
C1 C2 H2 119.9 . .
C4 C3 C2 121.5(2) . .
C4 C3 H3 119.2 . .
C2 C3 H3 119.2 . .
C5 C4 C3 120.3(3) . .
C5 C4 H4 119.9 . .
C3 C4 H4 119.9 . .
C4 C5 C6 117.6(3) . .
C4 C5 H5 121.2 . .
C6 C5 H5 121.2 . .
C5 C6 C1 123.4(2) . .
C5 C6 C7 127.0(2) . .
C1 C6 C7 109.4(2) . .
N1 C7 C6 114.2(2) . .
N1 C7 H7 122.9 . .
C6 C7 H7 122.9 . .
C9 C8 C12 120.8(2) . 2
C9 C8 N1 119.5(2) . .
C12 C8 N1 119.8(2) 2 .
C8 C9 C10 120.3(2) . .
C8 C9 H9 119.8 . .
C10 C9 H9 119.8 . .
C11 C10 C9 120.9(2) . .
C11 C10 H10 119.5 . .
C9 C10 H10 119.5 . .
C10 C11 C12 120.4(2) . .
C10 C11 H11 119.8 . .
C12 C11 H11 119.8 . .
C11 C12 C12 119.5(3) . 2
C11 C12 C8 122.7(2) . 2
C12 C12 C8 117.8(3) 2 2
C26 C21 C22 115.9(2) . .
C26 C21 B1 119.9(2) . .
C22 C21 B1 123.5(2) . .
C23 C22 C21 120.6(2) . .
C23 C22 C27 115.4(2) . .
C21 C22 C27 123.7(2) . .
C24 C23 C22 122.6(3) . .
C24 C23 H23 118.7 . .
C22 C23 H23 118.7 . .
C23 C24 C25 117.0(3) . .
C23 C24 C28 121.5(3) . .
C25 C24 C28 121.5(3) . .
C24 C25 C26 122.4(3) . .
C24 C25 H25 118.8 . .
C26 C25 H25 118.8 . .
C25 C26 C21 121.0(3) . .
C25 C26 C29 116.5(2) . .
C21 C26 C29 122.4(2) . .
C22 C27 H27A 109.5 . .
C22 C27 H27B 109.5 . .
H27A C27 H27B 109.5 . .
C22 C27 H27C 109.5 . .
H27A C27 H27C 109.5 . .
H27B C27 H27C 109.5 . .
C24 C28 H28A 109.5 . .
C24 C28 H28B 109.5 . .
H28A C28 H28B 109.5 . .
C24 C28 H28C 109.5 . .
H28A C28 H28C 109.5 . .
H28B C28 H28C 109.5 . .
C26 C29 H29A 109.5 . .
C26 C29 H29B 109.5 . .
H29A C29 H29B 109.5 . .
C26 C29 H29C 109.5 . .
H29A C29 H29C 109.5 . .
H29B C29 H29C 109.5 . .
C36 C31 C32 115.3(2) . .
C36 C31 B1 120.9(2) . .
C32 C31 B1 123.0(2) . .
C33 C32 C31 120.6(3) . .
C33 C32 C37 115.3(3) . .
C31 C32 C37 124.0(2) . .
C34 C33 C32 123.1(3) . .
C34 C33 H33 118.4 . .
C32 C33 H33 118.4 . .
C35 C34 C33 116.6(3) . .
C35 C34 C38 122.1(3) . .
C33 C34 C38 121.3(3) . .
C34 C35 C36 122.6(3) . .
C34 C35 H35 118.7 . .
C36 C35 H35 118.7 . .
C35 C36 C31 121.3(3) . .
C35 C36 C39 115.0(3) . .
C31 C36 C39 123.6(2) . .
C32 C37 H37A 109.5 . .
C32 C37 H37B 109.5 . .
H37A C37 H37B 109.5 . .
C32 C37 H37C 109.5 . .
H37A C37 H37C 109.5 . .
H37B C37 H37C 109.5 . .
C34 C38 H38A 109.5 . .
C34 C38 H38B 109.5 . .
H38A C38 H38B 109.5 . .
C34 C38 H38C 109.5 . .
H38A C38 H38C 109.5 . .
H38B C38 H38C 109.5 . .
C36 C39 H39A 109.5 . .
C36 C39 H39B 109.5 . .
H39A C39 H39B 109.5 . .
C36 C39 H39C 109.5 . .
H39A C39 H39C 109.5 . .
H39B C39 H39C 109.5 . .
Cl1 C100 Cl2 111.5(9) . .
Cl1 C100 H10A 109.3 . .
Cl2 C100 H10A 109.3 . .
Cl1 C100 H10B 109.3 . .
Cl2 C100 H10B 109.3 . .
H10A C100 H10B 108.0 . .
Cl4 C101 Cl3 111.4(4) . .
Cl4 C101 H10C 109.4 . .
Cl3 C101 H10C 109.4 . .
Cl4 C101 H10D 109.4 . .
Cl3 C101 H10D 109.4 . .
H10C C101 H10D 108.0 . .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
N1 C7 1.298(3) .
N1 C8 1.438(3) .
N1 B1 1.692(3) .
B1 C1 1.616(4) .
B1 C21 1.638(3) .
B1 C31 1.664(4) .
C1 C2 1.389(3) .
C1 C6 1.402(3) .
C2 C3 1.383(4) .
C2 H2 0.9400 .
C3 C4 1.382(4) .
C3 H3 0.9400 .
C4 C5 1.376(4) .
C4 H4 0.9400 .
C5 C6 1.397(4) .
C5 H5 0.9400 .
C6 C7 1.429(3) .
C7 H7 0.9400 .
C8 C9 1.366(4) .
C8 C12 1.431(3) 2
C9 C10 1.403(3) .
C9 H9 0.9400 .
C10 C11 1.361(4) .
C10 H10 0.9400 .
C11 C12 1.415(3) .
C11 H11 0.9400 .
C12 C12 1.425(4) 2
C12 C8 1.431(3) 2
C21 C26 1.416(4) .
C21 C22 1.418(4) .
C22 C23 1.397(4) .
C22 C27 1.512(4) .
C23 C24 1.379(4) .
C23 H23 0.9400 .
C24 C25 1.381(4) .
C24 C28 1.521(4) .
C25 C26 1.392(4) .
C25 H25 0.9400 .
C26 C29 1.514(4) .
C27 H27A 0.9700 .
C27 H27B 0.9700 .
C27 H27C 0.9700 .
C28 H28A 0.9700 .
C28 H28B 0.9700 .
C28 H28C 0.9700 .
C29 H29A 0.9700 .
C29 H29B 0.9700 .
C29 H29C 0.9700 .
C31 C36 1.414(4) .
C31 C32 1.428(4) .
C32 C33 1.397(4) .
C32 C37 1.511(4) .
C33 C34 1.378(5) .
C33 H33 0.9400 .
C34 C35 1.375(5) .
C34 C38 1.511(4) .
C35 C36 1.400(4) .
C35 H35 0.9400 .
C36 C39 1.514(4) .
C37 H37A 0.9700 .
C37 H37B 0.9700 .
C37 H37C 0.9700 .
C38 H38A 0.9700 .
C38 H38B 0.9700 .
C38 H38C 0.9700 .
C39 H39A 0.9700 .
C39 H39B 0.9700 .
C39 H39C 0.9700 .
C100 Cl1 1.721(9) .
C100 Cl2 1.726(9) .
C100 H10A 0.9800 .
C100 H10B 0.9800 .
C101 Cl4 1.715(6) .
C101 Cl3 1.738(6) .
C101 H10C 0.9800 .
C101 H10D 0.9800 .
