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#$Date: 2016-03-22 13:50:58 +0200 (Tue, 22 Mar 2016) $
#$Revision: 178980 $
#$URL: svn://www.crystallography.net/cod/cif/4/12/03/4120394.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_4120394
loop_
_publ_author_name
'Christian Reus'
'Sabine Weidlich'
'Michael Bolte'
'Hans-Wolfram Lerner'
'Matthias Wagner'
_publ_section_title
;
 C-Functionalized, Air- and Water-Stable
 9,10-Dihydro-9,10-diboraanthracenes: Efficient Blue to Red Emitting
 Luminophores
;
_journal_name_full               'Journal of the American Chemical Society'
_journal_page_first              12892
_journal_page_last               12907
_journal_paper_doi               10.1021/ja406766e
_journal_volume                  135
_journal_year                    2013
_chemical_formula_moiety         'C44 H40 B2 Cl6'
_chemical_formula_sum            'C44 H40 B2 Cl6'
_chemical_formula_weight         803.08
_chemical_name_systematic        ?
_space_group_IT_number           2
_symmetry_cell_setting           triclinic
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                105.904(9)
_cell_angle_beta                 93.977(10)
_cell_angle_gamma                116.008(9)
_cell_formula_units_Z            1
_cell_length_a                   9.5641(12)
_cell_length_b                   9.7285(11)
_cell_length_c                   13.4353(16)
_cell_measurement_reflns_used    7585
_cell_measurement_temperature    173(2)
_cell_measurement_theta_max      25.9
_cell_measurement_theta_min      3.3
_cell_volume                     1054.2(3)
_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 (Sheldrick, 2008)'
_computing_publication_material  SHELXL97
_computing_structure_refinement  'SHELXL97 (Sheldrick, 2008) '
_computing_structure_solution    'SHELXS97 (Sheldrick, 2008) '
_diffrn_ambient_temperature      173(2)
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_device_type  'STOE IPDS II two-circle-diffractometer'
_diffrn_measurement_method       ω
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0924
_diffrn_reflns_av_sigmaI/netI    0.0778
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            14674
_diffrn_reflns_theta_full        25.00
_diffrn_reflns_theta_max         25.03
_diffrn_reflns_theta_min         3.20
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.438
_exptl_absorpt_correction_T_max  0.9700
_exptl_absorpt_correction_T_min  0.9215
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'MULABS (Spek, 2003; Blessing, 1995)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.265
_exptl_crystal_description       plate
_exptl_crystal_F_000             416
_exptl_crystal_size_max          0.19
_exptl_crystal_size_mid          0.16
_exptl_crystal_size_min          0.07
_refine_diff_density_max         0.657
_refine_diff_density_min         -0.487
_refine_diff_density_rms         0.081
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.018
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     238
_refine_ls_number_reflns         3715
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.018
_refine_ls_R_factor_all          0.1191
_refine_ls_R_factor_gt           0.0791
_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)+(0.1370P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2070
_refine_ls_wR_factor_ref         0.2290
_reflns_number_gt                2344
_reflns_number_total             3715
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            ja406766e_si_001_04.cif
_cod_data_source_block           wa1311
_cod_original_cell_volume        1054.2(2)
_cod_database_code               4120394
loop_
_symmetry_equiv_pos_as_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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
B1 B 0.4086(5) 0.8468(6) 0.4048(3) 0.0305(9) Uani 1 1 d .
C1 C 0.4332(5) 0.8383(5) 0.5184(3) 0.0307(8) Uani 1 1 d .
C2 C 0.5199(5) 0.9818(5) 0.6082(3) 0.0286(8) Uani 1 1 d .
C3 C 0.5373(5) 0.9675(5) 0.7088(3) 0.0323(9) Uani 1 1 d .
H3 H 0.5955 1.0636 0.7688 0.039 Uiso 1 1 calc R
C4 C 0.4720(5) 0.8170(5) 0.7241(3) 0.0322(9) Uani 1 1 d .
C5 C 0.3874(5) 0.6783(5) 0.6356(3) 0.0386(10) Uani 1 1 d .
H5 H 0.3416 0.5747 0.6441 0.046 Uiso 1 1 calc R
C6 C 0.3681(5) 0.6882(5) 0.5344(3) 0.0384(10) Uani 1 1 d .
H6 H 0.3097 0.5911 0.4750 0.046 Uiso 1 1 calc R
C11 C 0.3186(5) 0.6906(5) 0.3036(3) 0.0295(8) Uani 1 1 d .
C12 C 0.1563(5) 0.6296(5) 0.2591(3) 0.0380(9) Uani 1 1 d .
C13 C 0.0829(5) 0.4965(5) 0.1652(3) 0.0411(10) Uani 1 1 d .
H13 H -0.0257 0.4580 0.1347 0.049 Uiso 1 1 calc R
C14 C 0.1628(5) 0.4186(5) 0.1148(3) 0.0382(10) Uani 1 1 d .
C15 C 0.3211(5) 0.4771(5) 0.1594(3) 0.0356(9) Uani 1 1 d .
H15 H 0.3772 0.4240 0.1263 0.043 Uiso 1 1 calc R
C16 C 0.4011(5) 0.6128(5) 0.2525(3) 0.0328(9) Uani 1 1 d .
C17 C 0.0635(6) 0.7075(7) 0.3133(5) 0.0583(13) Uani 1 1 d .
H17A H -0.0301 0.6813 0.2618 0.087 Uiso 1 1 calc R
H17B H 0.1314 0.8257 0.3423 0.087 Uiso 1 1 calc R
H17C H 0.0287 0.6663 0.3709 0.087 Uiso 1 1 calc R
C18 C 0.0812(7) 0.2766(6) 0.0120(4) 0.0545(13) Uani 1 1 d .
H18A H 0.0507 0.1749 0.0264 0.082 Uiso 1 1 calc R
H18B H 0.1544 0.2872 -0.0364 0.082 Uiso 1 1 calc R
H18C H -0.0143 0.2755 -0.0206 0.082 Uiso 1 1 calc R
C19 C 0.5764(6) 0.6785(6) 0.2963(4) 0.0486(11) Uani 1 1 d .
H19A H 0.6176 0.6176 0.2478 0.073 Uiso 1 1 calc R
H19B H 0.5907 0.6669 0.3659 0.073 Uiso 1 1 calc R
H19C H 0.6344 0.7937 0.3036 0.073 Uiso 1 1 calc R
C21 C 0.4921(5) 0.8102(5) 0.8332(3) 0.0341(9) Uani 1 1 d .
C22 C 0.3712(6) 0.6897(5) 0.8601(3) 0.0413(10) Uani 1 1 d .
H22 H 0.2764 0.6113 0.8084 0.050 Uiso 1 1 calc R
C23 C 0.3889(6) 0.6838(6) 0.9627(4) 0.0470(11) Uani 1 1 d .
H23 H 0.3055 0.6019 0.9805 0.056 Uiso 1 1 calc R
C24 C 0.5246(6) 0.7944(6) 1.0371(3) 0.0495(12) Uani 1 1 d .
H24 H 0.5362 0.7882 1.1063 0.059 Uiso 1 1 calc R
C25 C 0.6458(6) 0.9158(6) 1.0127(4) 0.0478(11) Uani 1 1 d .
H25 H 0.7394 0.9945 1.0653 0.057 Uiso 1 1 calc R
C26 C 0.6298(5) 0.9219(6) 0.9099(3) 0.0401(10) Uani 1 1 d .
H26 H 0.7142 1.0036 0.8926 0.048 Uiso 1 1 calc R
C1L C -0.0885(6) 0.7709(6) 0.6775(4) 0.0525(12) Uani 1 1 d .
H1L H -0.1563 0.6802 0.7023 0.063 Uiso 1 1 calc R
Cl1 Cl -0.2077(2) 0.7694(2) 0.57305(14) 0.0918(7) Uani 1 1 d .
Cl2 Cl -0.0179(2) 0.9527(2) 0.78255(12) 0.0885(6) Uani 1 1 d .
Cl3 Cl 0.0648(2) 0.7375(3) 0.63692(18) 0.0970(7) 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'
Cl Cl 0.1484 0.1585 '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
C1 B1 C2 118.4(4) . 2_676
C1 B1 C11 122.4(4) . .
C2 B1 C11 119.2(3) 2_676 .
C6 C1 C2 118.4(3) . .
C6 C1 B1 120.5(4) . .
C2 C1 B1 121.1(3) . .
C3 C2 C1 118.9(4) . .
C3 C2 B1 120.7(3) . 2_676
C1 C2 B1 120.5(3) . 2_676
C4 C3 C2 122.5(4) . .
C4 C3 H3 118.8 . .
C2 C3 H3 118.8 . .
C5 C4 C3 117.9(3) . .
C5 C4 C21 122.3(4) . .
C3 C4 C21 119.8(4) . .
C4 C5 C6 121.1(4) . .
C4 C5 H5 119.4 . .
C6 C5 H5 119.4 . .
C5 C6 C1 121.3(4) . .
C5 C6 H6 119.3 . .
C1 C6 H6 119.3 . .
C16 C11 C12 118.7(4) . .
C16 C11 B1 120.2(4) . .
C12 C11 B1 121.0(3) . .
C13 C12 C11 119.4(4) . .
C13 C12 C17 120.6(4) . .
C11 C12 C17 120.0(4) . .
C14 C13 C12 122.3(4) . .
C14 C13 H13 118.8 . .
C12 C13 H13 118.8 . .
C15 C14 C13 118.2(4) . .
C15 C14 C18 120.6(4) . .
C13 C14 C18 121.2(4) . .
C14 C15 C16 121.6(4) . .
C14 C15 H15 119.2 . .
C16 C15 H15 119.2 . .
C15 C16 C11 119.8(4) . .
C15 C16 C19 120.3(4) . .
C11 C16 C19 119.9(4) . .
C12 C17 H17A 109.5 . .
C12 C17 H17B 109.5 . .
H17A C17 H17B 109.5 . .
C12 C17 H17C 109.5 . .
H17A C17 H17C 109.5 . .
H17B C17 H17C 109.5 . .
C14 C18 H18A 109.5 . .
C14 C18 H18B 109.5 . .
H18A C18 H18B 109.5 . .
C14 C18 H18C 109.5 . .
H18A C18 H18C 109.5 . .
H18B C18 H18C 109.5 . .
C16 C19 H19A 109.5 . .
C16 C19 H19B 109.5 . .
H19A C19 H19B 109.5 . .
C16 C19 H19C 109.5 . .
H19A C19 H19C 109.5 . .
H19B C19 H19C 109.5 . .
C26 C21 C22 118.5(4) . .
C26 C21 C4 121.4(4) . .
C22 C21 C4 120.1(4) . .
C21 C22 C23 120.3(4) . .
C21 C22 H22 119.8 . .
C23 C22 H22 119.8 . .
C24 C23 C22 120.4(4) . .
C24 C23 H23 119.8 . .
C22 C23 H23 119.8 . .
C23 C24 C25 120.4(4) . .
C23 C24 H24 119.8 . .
C25 C24 H24 119.8 . .
C24 C25 C26 119.6(5) . .
C24 C25 H25 120.2 . .
C26 C25 H25 120.2 . .
C21 C26 C25 120.7(4) . .
C21 C26 H26 119.6 . .
C25 C26 H26 119.6 . .
Cl3 C1L Cl1 111.2(3) . .
Cl3 C1L Cl2 111.9(3) . .
Cl1 C1L Cl2 109.8(3) . .
Cl3 C1L H1L 107.9 . .
Cl1 C1L H1L 107.9 . .
Cl2 C1L H1L 107.9 . .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
B1 C1 1.559(6) .
B1 C2 1.567(6) 2_676
B1 C11 1.567(6) .
C1 C6 1.400(6) .
C1 C2 1.420(5) .
C2 C3 1.402(5) .
C2 B1 1.567(6) 2_676
C3 C4 1.399(6) .
C3 H3 0.9500 .
C4 C5 1.385(6) .
C4 C21 1.488(5) .
C5 C6 1.395(6) .
C5 H5 0.9500 .
C6 H6 0.9500 .
C11 C16 1.407(5) .
C11 C12 1.410(6) .
C12 C13 1.395(6) .
C12 C17 1.507(7) .
C13 C14 1.383(6) .
C13 H13 0.9500 .
C14 C15 1.381(6) .
C14 C18 1.511(6) .
C15 C16 1.403(6) .
C15 H15 0.9500 .
C16 C19 1.511(6) .
C17 H17A 0.9800 .
C17 H17B 0.9800 .
C17 H17C 0.9800 .
C18 H18A 0.9800 .
C18 H18B 0.9800 .
C18 H18C 0.9800 .
C19 H19A 0.9800 .
C19 H19B 0.9800 .
C19 H19C 0.9800 .
C21 C26 1.386(6) .
C21 C22 1.394(6) .
C22 C23 1.396(6) .
C22 H22 0.9500 .
C23 C24 1.359(7) .
C23 H23 0.9500 .
C24 C25 1.382(7) .
C24 H24 0.9500 .
C25 C26 1.399(6) .
C25 H25 0.9500 .
C26 H26 0.9500 .
C1L Cl3 1.727(5) .
C1L Cl1 1.738(5) .
C1L Cl2 1.740(5) .
C1L H1L 1.0000 .
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 B1 C1 C6 178.4(4) 2_676 .
C11 B1 C1 C6 -3.0(6) . .
C2 B1 C1 C2 -0.8(6) 2_676 .
C11 B1 C1 C2 177.8(4) . .
C6 C1 C2 C3 0.2(6) . .
B1 C1 C2 C3 179.4(4) . .
C6 C1 C2 B1 -178.4(4) . 2_676
B1 C1 C2 B1 0.9(6) . 2_676
C1 C2 C3 C4 -0.1(6) . .
B1 C2 C3 C4 178.4(4) 2_676 .
C2 C3 C4 C5 -0.1(6) . .
C2 C3 C4 C21 -178.9(4) . .
C3 C4 C5 C6 0.2(6) . .
C21 C4 C5 C6 179.0(4) . .
C4 C5 C6 C1 -0.2(7) . .
C2 C1 C6 C5 -0.1(6) . .
B1 C1 C6 C5 -179.3(4) . .
C1 B1 C11 C16 -85.5(5) . .
C2 B1 C11 C16 93.2(4) 2_676 .
C1 B1 C11 C12 97.5(5) . .
C2 B1 C11 C12 -83.8(5) 2_676 .
C16 C11 C12 C13 -1.1(6) . .
B1 C11 C12 C13 175.9(4) . .
C16 C11 C12 C17 178.5(4) . .
B1 C11 C12 C17 -4.5(6) . .
C11 C12 C13 C14 1.6(6) . .
C17 C12 C13 C14 -178.0(4) . .
C12 C13 C14 C15 -0.7(6) . .
C12 C13 C14 C18 -178.9(4) . .
C13 C14 C15 C16 -0.8(6) . .
C18 C14 C15 C16 177.4(4) . .
C14 C15 C16 C11 1.3(6) . .
C14 C15 C16 C19 -177.0(4) . .
C12 C11 C16 C15 -0.3(6) . .
B1 C11 C16 C15 -177.3(4) . .
C12 C11 C16 C19 178.0(4) . .
B1 C11 C16 C19 1.0(6) . .
C5 C4 C21 C26 146.7(4) . .
C3 C4 C21 C26 -34.5(6) . .
C5 C4 C21 C22 -33.3(6) . .
C3 C4 C21 C22 145.4(4) . .
C26 C21 C22 C23 0.6(6) . .
C4 C21 C22 C23 -179.4(4) . .
C21 C22 C23 C24 -0.6(7) . .
C22 C23 C24 C25 1.1(7) . .
C23 C24 C25 C26 -1.6(7) . .
C22 C21 C26 C25 -1.1(6) . .
C4 C21 C26 C25 178.9(4) . .
C24 C25 C26 C21 1.6(7) . .
