#------------------------------------------------------------------------------
#$Date: 2016-03-26 17:29:18 +0200 (Sat, 26 Mar 2016) $
#$Revision: 180396 $
#$URL: svn://www.crystallography.net/cod/cif/7/20/65/7206588.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_7206588
loop_
_publ_author_name
'Li, Di'
'Wang, Kai'
'Huang, Shuo'
'Qu, Songnan'
'Liu, Xingyuan'
'Zhu, Qingxin'
'Zhang, Hongyu'
'Wang, Yue'
_publ_section_title
;
 Brightly fluorescent red organic solids bearing boron-bridged
 π--conjugated skeletons
;
_journal_issue                   39
_journal_name_full               'Journal of Materials Chemistry'
_journal_page_first              15298
_journal_paper_doi               10.1039/c1jm12498f
_journal_volume                  21
_journal_year                    2011
_chemical_formula_sum            'C44 H30 B2 N2 O4'
_chemical_formula_weight         672.32
_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                74.48(2)
_cell_angle_beta                 75.97(2)
_cell_angle_gamma                65.43(3)
_cell_formula_units_Z            1
_cell_length_a                   8.220(5)
_cell_length_b                   8.960(7)
_cell_length_c                   13.113(7)
_cell_measurement_temperature    293(2)
_cell_volume                     836.8(10)
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      293(2)
_diffrn_measured_fraction_theta_full 0.986
_diffrn_measured_fraction_theta_max 0.986
_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  0.0889
_diffrn_reflns_av_sigmaI/netI    0.1309
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            8244
_diffrn_reflns_theta_full        27.48
_diffrn_reflns_theta_max         27.48
_diffrn_reflns_theta_min         2.98
_exptl_absorpt_coefficient_mu    0.085
_exptl_absorpt_correction_T_max  0.9961
_exptl_absorpt_correction_T_min  0.9692
_exptl_absorpt_correction_type   multi-scan
_exptl_crystal_density_diffrn    1.334
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             350
_exptl_crystal_size_max          0.37
_exptl_crystal_size_mid          0.10
_exptl_crystal_size_min          0.05
_refine_diff_density_max         0.227
_refine_diff_density_min         -0.250
_refine_diff_density_rms         0.054
_refine_ls_extinction_coef       0.027(4)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     SHELXL
_refine_ls_goodness_of_fit_ref   1.015
_refine_ls_hydrogen_treatment    riding
_refine_ls_matrix_type           full
_refine_ls_number_parameters     236
_refine_ls_number_reflns         3776
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.015
_refine_ls_R_factor_all          0.1801
_refine_ls_R_factor_gt           0.0786
_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)+(0.0591P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1304
_refine_ls_wR_factor_ref         0.1631
_reflns_number_gt                1768
_reflns_number_total             3776
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            c1jm12498f.txt
_cod_data_source_block           1
_cod_original_cell_volume        836.7(10)
_cod_original_sg_symbol_H-M      P-1
_cod_database_code               7206588
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 0.2542(5) 0.2609(5) 0.2127(3) 0.0348(8) Uani 1 1 d .
C1 C 1.1497(4) 0.3338(4) -0.1357(2) 0.0345(7) Uani 1 1 d .
C2 C 1.3265(4) 0.2248(4) -0.1380(2) 0.0429(8) Uani 1 1 d .
H2 H 1.3598 0.1155 -0.1000 0.051 Uiso 1 1 calc R
C3 C 1.4513(5) 0.2899(5) -0.2013(3) 0.0486(9) Uani 1 1 d .
H3 H 1.5738 0.2235 -0.2047 0.058 Uiso 1 1 calc R
C4 C 1.3987(4) 0.4514(5) -0.2595(3) 0.0487(9) Uani 1 1 d .
H4 H 1.4876 0.4895 -0.3015 0.058 Uiso 1 1 calc R
C5 C 1.2190(4) 0.5591(4) -0.2580(2) 0.0450(8) Uani 1 1 d .
H5 H 1.1849 0.6673 -0.2977 0.054 Uiso 1 1 calc R
C6 C 1.0939(4) 0.4949(4) -0.1935(2) 0.0345(7) Uani 1 1 d .
C7 C 0.8556(4) 0.4466(4) -0.1007(2) 0.0336(7) Uani 1 1 d .
C8 C 0.6740(4) 0.4685(4) -0.0506(2) 0.0341(7) Uani 1 1 d .
C9 C 0.6252(4) 0.3357(4) 0.0104(2) 0.0384(8) Uani 1 1 d .
H9 H 0.7108 0.2270 0.0161 0.046 Uiso 1 1 calc R
C10 C 0.4509(4) 0.3651(4) 0.0620(2) 0.0354(8) Uani 1 1 d .
C11 C 0.1735(4) 0.1176(4) 0.2391(2) 0.0337(7) Uani 1 1 d .
C12 C 0.1060(5) 0.0892(4) 0.1616(3) 0.0495(9) Uani 1 1 d .
H12 H 0.1163 0.1493 0.0921 0.059 Uiso 1 1 calc R
C13 C 0.0241(5) -0.0251(5) 0.1842(3) 0.0590(10) Uani 1 1 d .
H13 H -0.0215 -0.0394 0.1307 0.071 Uiso 1 1 calc R
C14 C 0.0100(5) -0.1176(5) 0.2852(3) 0.0648(11) Uani 1 1 d .
H14 H -0.0455 -0.1945 0.3006 0.078 Uiso 1 1 calc R
C15 C 0.0778(5) -0.0962(5) 0.3629(3) 0.0617(11) Uani 1 1 d .
H15 H 0.0701 -0.1599 0.4314 0.074 Uiso 1 1 calc R
C16 C 0.1584(5) 0.0205(4) 0.3403(2) 0.0464(9) Uani 1 1 d .
H16 H 0.2034 0.0338 0.3945 0.056 Uiso 1 1 calc R
C17 C 0.3227(4) 0.2792(4) 0.3107(2) 0.0352(7) Uani 1 1 d .
C18 C 0.2162(5) 0.3874(5) 0.3814(3) 0.0516(10) Uani 1 1 d .
H18 H 0.1006 0.4610 0.3683 0.062 Uiso 1 1 calc R
C19 C 0.2783(5) 0.3883(6) 0.4713(3) 0.0623(11) Uani 1 1 d .
H19 H 0.2047 0.4621 0.5169 0.075 Uiso 1 1 calc R
C20 C 0.4483(6) 0.2797(6) 0.4921(3) 0.0618(11) Uani 1 1 d .
H20 H 0.4898 0.2787 0.5523 0.074 Uiso 1 1 calc R
C21 C 0.5563(5) 0.1729(5) 0.4236(3) 0.0570(10) Uani 1 1 d .
H21 H 0.6719 0.0999 0.4370 0.068 Uiso 1 1 calc R
C22 C 0.4941(5) 0.1734(4) 0.3351(2) 0.0461(9) Uani 1 1 d .
H22 H 0.5698 0.0999 0.2898 0.055 Uiso 1 1 calc R
N1 N 0.9031(3) 0.5635(3) -0.16918(18) 0.0342(6) Uani 1 1 d .
O1 O 0.9968(3) 0.3037(3) -0.07691(15) 0.0387(5) Uani 1 1 d .
O2 O 0.4006(3) 0.2363(3) 0.11633(15) 0.0372(5) 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'
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_1
_geom_angle_site_symmetry_3
O2 B1 C17 111.4(2) . .
O2 B1 C11 109.7(3) . .
C17 B1 C11 114.8(3) . .
O2 B1 N1 102.8(2) . 2_665
C17 B1 N1 110.0(3) . 2_665
C11 B1 N1 107.4(2) . 2_665
C2 C1 C6 124.5(3) . .
C2 C1 O1 127.2(3) . .
C6 C1 O1 108.2(3) . .
C1 C2 C3 114.8(3) . .
C1 C2 H2 122.6 . .
C3 C2 H2 122.6 . .
C2 C3 C4 121.7(3) . .
C2 C3 H3 119.1 . .
C4 C3 H3 119.1 . .
C3 C4 C5 122.8(3) . .
C3 C4 H4 118.6 . .
C5 C4 H4 118.6 . .
C6 C5 C4 115.7(3) . .
C6 C5 H5 122.2 . .
C4 C5 H5 122.2 . .
C1 C6 C5 120.5(3) . .
C1 C6 N1 106.6(2) . .
C5 C6 N1 132.9(3) . .
N1 C7 O1 113.3(3) . .
N1 C7 C8 124.4(3) . .
O1 C7 C8 122.2(3) . .
C9 C8 C10 122.0(3) . 2_665
C9 C8 C7 122.6(3) . .
C10 C8 C7 115.3(3) 2_665 .
C10 C9 C8 120.2(3) . .
C10 C9 H9 119.9 . .
C8 C9 H9 119.9 . .
O2 C10 C9 120.4(3) . .
O2 C10 C8 121.7(3) . 2_665
C9 C10 C8 117.8(3) . 2_665
C16 C11 C12 116.0(3) . .
C16 C11 B1 122.8(3) . .
C12 C11 B1 121.1(3) . .
C13 C12 C11 122.3(3) . .
C13 C12 H12 118.9 . .
C11 C12 H12 118.9 . .
C14 C13 C12 120.2(3) . .
C14 C13 H13 119.9 . .
C12 C13 H13 119.9 . .
C15 C14 C13 119.5(3) . .
C15 C14 H14 120.3 . .
C13 C14 H14 120.3 . .
C14 C15 C16 120.3(3) . .
C14 C15 H15 119.8 . .
C16 C15 H15 119.8 . .
C11 C16 C15 121.8(3) . .
C11 C16 H16 119.1 . .
C15 C16 H16 119.1 . .
C22 C17 C18 115.8(3) . .
C22 C17 B1 119.7(3) . .
C18 C17 B1 124.3(3) . .
C19 C18 C17 121.9(3) . .
C19 C18 H18 119.1 . .
C17 C18 H18 119.1 . .
C20 C19 C18 119.8(4) . .
C20 C19 H19 120.1 . .
C18 C19 H19 120.1 . .
C21 C20 C19 119.6(3) . .
C21 C20 H20 120.2 . .
C19 C20 H20 120.2 . .
C20 C21 C22 120.2(4) . .
C20 C21 H21 119.9 . .
C22 C21 H21 119.9 . .
C21 C22 C17 122.8(3) . .
C21 C22 H22 118.6 . .
C17 C22 H22 118.6 . .
C7 N1 C6 106.4(3) . .
C7 N1 B1 119.0(2) . 2_665
C6 N1 B1 134.4(2) . 2_665
C7 O1 C1 105.4(2) . .
C10 O2 B1 119.4(2) . .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
B1 O2 1.511(4) .
B1 C17 1.593(4) .
B1 C11 1.601(5) .
B1 N1 1.630(4) 2_665
C1 C2 1.371(4) .
C1 C6 1.379(4) .
C1 O1 1.396(3) .
C2 C3 1.381(4) .
C2 H2 0.9300 .
C3 C4 1.383(5) .
C3 H3 0.9300 .
C4 C5 1.387(4) .
C4 H4 0.9300 .
C5 C6 1.383(4) .
C5 H5 0.9300 .
C6 N1 1.414(4) .
C7 N1 1.312(4) .
C7 O1 1.346(4) .
C7 C8 1.431(4) .
C8 C9 1.396(4) .
C8 C10 1.408(4) 2_665
C9 C10 1.375(4) .
C9 H9 0.9300 .
C10 O2 1.350(3) .
C10 C8 1.408(4) 2_665
C11 C16 1.388(4) .
C11 C12 1.392(4) .
C12 C13 1.379(5) .
C12 H12 0.9300 .
C13 C14 1.368(5) .
C13 H13 0.9300 .
C14 C15 1.362(5) .
C14 H14 0.9300 .
C15 C16 1.391(4) .
C15 H15 0.9300 .
C16 H16 0.9300 .
C17 C22 1.390(4) .
C17 C18 1.396(4) .
C18 C19 1.395(4) .
C18 H18 0.9300 .
C19 C20 1.373(5) .
C19 H19 0.9300 .
C20 C21 1.370(5) .
C20 H20 0.9300 .
C21 C22 1.374(4) .
C21 H21 0.9300 .
C22 H22 0.9300 .
N1 B1 1.630(4) 2_665
