#------------------------------------------------------------------------------
#$Date: 2016-02-13 14:50:18 +0200 (Sat, 13 Feb 2016) $
#$Revision: 176428 $
#$URL: svn://www.crystallography.net/cod/cif/7/03/59/7035936.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_7035936
loop_
_publ_author_name
'Zhang, Zhenyu'
'Zhang, Zuolun'
'Ye, Kaiqi'
'Zhang, Jingying'
'Zhang, Hongyu'
'Wang, Yue'
_publ_section_title
;
 Diboron complexes with bis-spiro structures as high-performance blue
 emitters for OLEDs.
;
_journal_issue                   32
_journal_name_full
'Dalton transactions (Cambridge, England : 2003)'
_journal_page_first              14436
_journal_page_last               14443
_journal_paper_doi               10.1039/c5dt02093j
_journal_volume                  44
_journal_year                    2015
_chemical_formula_sum            'C50 H34 B2 N4 O2'
_chemical_formula_weight         744.43
_chemical_name_common            dibm
_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
_audit_update_record
;
2015-05-22 deposited with the CCDC.
2015-07-08 downloaded from the CCDC.
;
_cell_angle_alpha                90.00
_cell_angle_beta                 110.48(3)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   23.440(5)
_cell_length_b                   9.4816(19)
_cell_length_c                   18.355(4)
_cell_measurement_temperature    293(2)
_cell_volume                     3821.5(16)
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      293(2)
_diffrn_measured_fraction_theta_full 0.990
_diffrn_measured_fraction_theta_max 0.990
_diffrn_measurement_device_type  'Rigaku RAXIS-RAPID'
_diffrn_measurement_method       'ω scans'
_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  0.0447
_diffrn_reflns_av_sigmaI/netI    0.0420
_diffrn_reflns_limit_h_max       28
_diffrn_reflns_limit_h_min       -30
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       23
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_number            17271
_diffrn_reflns_theta_full        27.48
_diffrn_reflns_theta_max         27.48
_diffrn_reflns_theta_min         3.09
_exptl_absorpt_coefficient_mu    0.079
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.294
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             1552
_exptl_crystal_size_max          0.598
_exptl_crystal_size_mid          0.433
_exptl_crystal_size_min          0.425
_refine_diff_density_max         0.213
_refine_diff_density_min         -0.157
_refine_diff_density_rms         0.043
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.990
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     330
_refine_ls_number_reflns         4341
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.990
_refine_ls_R_factor_all          0.0873
_refine_ls_R_factor_gt           0.0532
_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)+(0.1056P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1445
_refine_ls_wR_factor_ref         0.1722
_reflns_number_gt                2670
_reflns_number_total             4341
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            c5dt02093j2.cif
_cod_data_source_block           z1
_cod_depositor_comments
'Adding full bibliography for 7035935--7035936.cif.'
_cod_original_cell_volume        3821.6(13)
_cod_original_sg_symbol_H-M      C2/c
_cod_database_code               7035936
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
O1 O 0.09641(6) 1.11227(14) 0.11781(7) 0.0573(4) Uani 1 1 d
N1 N 0.07173(6) 0.86880(16) 0.14290(8) 0.0450(4) Uani 1 1 d
C14 C 0.15396(7) 0.99410(19) 0.23817(9) 0.0416(4) Uani 1 1 d
C13 C 0.11485(8) 0.87234(19) 0.21229(10) 0.0433(4) Uani 1 1 d
C19 C 0.14052(8) 1.11148(18) 0.18566(9) 0.0417(4) Uani 1 1 d
C20 C 0.06172(8) 0.9427(2) 0.00219(10) 0.0472(4) Uani 1 1 d
N2 N 0.11737(8) 0.74745(17) 0.25045(9) 0.0529(4) Uani 1 1 d
C21 C 0.01570(8) 0.95506(19) -0.07049(9) 0.0435(4) Uani 1 1 d
C18 C 0.17649(9) 1.2323(2) 0.20837(11) 0.0504(5) Uani 1 1 d
C15 C 0.20359(9) 1.0029(2) 0.30666(11) 0.0541(5) Uani 1 1 d
C7 C 0.14853(9) 0.7098(2) 0.33053(12) 0.0573(5) Uani 1 1 d
C22 C 0.02891(10) 0.9104(2) -0.13614(11) 0.0547(5) Uani 1 1 d
C23 C 0.08417(11) 0.8535(3) -0.13060(14) 0.0650(6) Uani 1 1 d
C17 C 0.22471(9) 1.2370(2) 0.27818(12) 0.0588(5) Uani 1 1 d
C1 C 0.04487(9) 0.7349(2) 0.13245(11) 0.0530(5) Uani 1 1 d
B1 B 0.05242(9) 0.9934(2) 0.08073(11) 0.0454(5) Uani 1 1 d
C12 C 0.13075(10) 0.7698(3) 0.38738(12) 0.0627(6) Uani 1 1 d
C6 C 0.07288(10) 0.6586(2) 0.19846(12) 0.0561(5) Uani 1 1 d
C16 C 0.23920(10) 1.1215(3) 0.32679(12) 0.0628(6) Uani 1 1 d
C24 C 0.12898(12) 0.8399(3) -0.05856(16) 0.0737(7) Uani 1 1 d
C2 C -0.00148(11) 0.6765(3) 0.06979(15) 0.0665(6) Uani 1 1 d
C8 C 0.19143(12) 0.6041(3) 0.34735(17) 0.0809(8) Uani 1 1 d
C3 C -0.01740(13) 0.5391(3) 0.07856(18) 0.0790(8) Uani 1 1 d
C25 C 0.11785(10) 0.8850(3) 0.00594(13) 0.0650(6) Uani 1 1 d
C4 C 0.01258(15) 0.4624(3) 0.1466(2) 0.0898(9) Uani 1 1 d
C5 C 0.05837(13) 0.5201(3) 0.20866(18) 0.0773(7) Uani 1 1 d
C11 C 0.15665(13) 0.7225(4) 0.46334(14) 0.0840(8) Uani 1 1 d
C10 C 0.19783(15) 0.6157(4) 0.48010(18) 0.0985(11) Uani 1 1 d
C9 C 0.21577(15) 0.5570(4) 0.4232(2) 0.1031(11) Uani 1 1 d
H1 H 0.1657(8) 1.314(2) 0.1752(11) 0.052(5) Uiso 1 1 d
H2 H -0.0008(10) 0.921(2) -0.1823(13) 0.067(7) Uiso 1 1 d
H3 H -0.0493(9) 0.500(2) 0.0356(12) 0.062(6) Uiso 1 1 d
H4 H 0.2134(9) 0.929(2) 0.3428(12) 0.064(6) Uiso 1 1 d
H5 H 0.2745(11) 1.120(3) 0.3846(14) 0.085(7) Uiso 1 1 d
H6 H 0.2521(9) 1.326(2) 0.2939(11) 0.060(6) Uiso 1 1 d
H7 H 0.1508(10) 0.879(2) 0.0628(14) 0.073(7) Uiso 1 1 d
H8 H 0.1699(13) 0.798(3) -0.0469(15) 0.101(9) Uiso 1 1 d
H9 H -0.0026(10) 0.373(3) 0.1477(13) 0.077(7) Uiso 1 1 d
H10 H -0.0209(11) 0.739(3) 0.0345(14) 0.079(8) Uiso 1 1 d
H11 H 0.0919(14) 0.826(3) -0.1697(17) 0.111(10) Uiso 1 1 d
H12 H 0.0976(10) 0.841(3) 0.3720(13) 0.072(7) Uiso 1 1 d
H13 H 0.2040(11) 0.562(3) 0.3006(14) 0.084(7) Uiso 1 1 d
H14 H 0.0822(11) 0.475(3) 0.2608(15) 0.090(8) Uiso 1 1 d
H15 H 0.2429(16) 0.481(4) 0.4251(18) 0.129(12) Uiso 1 1 d
H16 H 0.2181(17) 0.578(4) 0.535(2) 0.155(14) Uiso 1 1 d
H18 H 0.1390(13) 0.767(3) 0.4963(16) 0.095(9) Uiso 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'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 '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_3
C19 O1 B1 127.42(14) .
C13 N1 C1 108.11(15) .
C13 N1 B1 126.97(14) .
C1 N1 B1 124.92(15) .
C15 C14 C19 118.73(17) .
C15 C14 C13 125.50(17) .
C19 C14 C13 115.71(15) .
N1 C13 N2 110.71(16) .
N1 C13 C14 121.33(15) .
N2 C13 C14 127.90(16) .
O1 C19 C18 118.15(16) .
O1 C19 C14 123.91(15) .
C18 C19 C14 117.94(16) .
C21 C20 C25 118.49(17) .
C21 C20 B1 122.04(16) .
C25 C20 B1 119.47(17) .
C13 N2 C6 106.28(16) .
C13 N2 C7 130.83(17) .
C6 N2 C7 122.07(16) .
C20 C21 C22 117.64(17) .
C20 C21 B1 122.54(15) 5_575
C22 C21 B1 119.65(16) 5_575
C17 C18 C19 121.05(19) .
C16 C15 C14 122.20(19) .
C12 C7 C8 121.5(2) .
C12 C7 N2 119.51(18) .
C8 C7 N2 118.7(2) .
C23 C22 C21 122.5(2) .
C22 C23 C24 119.4(2) .
C16 C17 C18 120.77(19) .
C6 C1 C2 121.1(2) .
C6 C1 N1 107.79(17) .
C2 C1 N1 131.1(2) .
O1 B1 N1 104.54(14) .
O1 B1 C20 109.93(14) .
N1 B1 C20 109.08(16) .
O1 B1 C21 108.42(16) 5_575
N1 B1 C21 109.19(14) 5_575
C20 B1 C21 115.15(15) 5_575
C7 C12 C11 119.2(2) .
C1 C6 C5 123.9(2) .
C1 C6 N2 107.09(17) .
C5 C6 N2 129.0(2) .
C15 C16 C17 119.21(19) .
C25 C24 C23 119.3(2) .
C3 C2 C1 116.4(3) .
C7 C8 C9 118.2(3) .
C2 C3 C4 121.4(3) .
C24 C25 C20 122.6(2) .
C5 C4 C3 122.2(3) .
C4 C5 C6 115.0(3) .
C10 C11 C12 119.7(3) .
C11 C10 C9 120.9(3) .
C10 C9 C8 120.5(3) .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
O1 C19 1.311(2) .
O1 B1 1.518(2) .
N1 C13 1.321(2) .
N1 C1 1.400(2) .
N1 B1 1.594(2) .
C14 C15 1.385(3) .
C14 C19 1.433(2) .
C14 C13 1.447(2) .
C13 N2 1.366(2) .
C19 C18 1.397(3) .
C20 C21 1.396(2) .
C20 C25 1.404(3) .
C20 B1 1.605(3) .
N2 C6 1.418(3) .
N2 C7 1.439(2) .
C21 C22 1.410(2) .
C21 B1 1.617(3) 5_575
C18 C17 1.381(3) .
C15 C16 1.372(3) .
C7 C12 1.375(3) .
C7 C8 1.377(3) .
C22 C23 1.374(3) .
C23 C24 1.377(4) .
C17 C16 1.378(3) .
C1 C6 1.366(3) .
C1 C2 1.391(3) .
B1 C21 1.617(3) 5_575
C12 C11 1.386(3) .
C6 C5 1.386(3) .
C24 C25 1.367(3) .
C2 C3 1.380(4) .
C8 C9 1.382(4) .
C3 C4 1.403(4) .
C4 C5 1.376(4) .
C11 C10 1.357(5) .
C10 C9 1.372(5) .
