#------------------------------------------------------------------------------
#$Date: 2019-09-23 10:35:23 +0300 (Mon, 23 Sep 2019) $
#$Revision: 218698 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/23/40/7234043.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_7234043
loop_
_publ_author_name
'Krzysztof Durka'
'Ireneusz Glowacki'
'Sergiusz Lulinski'
'Beata Luszczynska'
'Jaromir Smetek'
'Pawel Szczepanik'
'Janusz Serwatowski'
'Urszula E. Wawrzyniak'
'Grzegorz Wesela-Bauman'
'Ewelina Witkowska'
'Gabriela Wiosna-Salyga'
'Krzysztof Wozniak'
_publ_section_title
;
 Efficient 8-oxyquinolinato emitters based on a
 9,10-dihydro-9,10-diboraanthracene scaffold for applications in
 optoelectronic devices
;
_journal_name_full               'Journal of Materials Chemistry C'
_journal_page_first              1354
_journal_page_last               1364
_journal_paper_doi               10.1039/C4TC02350A
_journal_volume                  3
_journal_year                    2015
_chemical_formula_moiety         'C26 H16 B2 N2 O2 S2'
_chemical_formula_sum            'C26 H16 B2 N2 O2 S2'
_chemical_formula_weight         474.15
_chemical_melting_point          360.7
_chemical_name_systematic
;
 4,8-bis(8-oxyquinolinato)-4,8-Dihydro-p-diborino[2,3-b:5,6-b']dithiophene
;
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_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                92.99(2)
_cell_angle_beta                 101.30(1)
_cell_angle_gamma                113.32(1)
_cell_formula_units_Z            1
_cell_length_a                   7.9127(4)
_cell_length_b                   9.3250(4)
_cell_length_c                   9.8060(4)
_cell_measurement_reflns_used    622
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      27.157
_cell_measurement_theta_min      4.020
_cell_volume                     644.76(9)
_computing_cell_refinement       'Bruker APEX2 software'
_computing_data_collection       'Bruker APEX2 software'
_computing_data_reduction
;
 SAINT intergration software, Bruker AXS
 SORTAV, R. H. Blessing, Acta Cryst., 1995, A51, 33
;
_computing_structure_refinement
;
 SHELXS-97, G. M. Sheldrick, Acta. Cryst., 2008, A64, 112
;
_computing_structure_solution
;
 SHELXS-97, G. M. Sheldrick, Acta. Cryst., 2008, A64, 112
;
_diffrn_ambient_temperature      100(2)
_diffrn_detector                 'APEXII CCD camera'
_diffrn_measured_fraction_theta_full 0.989
_diffrn_measured_fraction_theta_max 0.989
_diffrn_measurement_device       'κ-geometry diffractometer'
_diffrn_measurement_device_type  'Bruker APEXII'
_diffrn_measurement_method       'omega scans'
_diffrn_orient_matrix_type       'X-axis to radiation source'
_diffrn_radiation_monochromator  'multi-layer optics'
_diffrn_radiation_probe          x-ray
_diffrn_radiation_source         'TXS rotating anode'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0267
_diffrn_reflns_av_sigmaI/netI    0.0397
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_number            13958
_diffrn_reflns_reduction_process
;
 Scaled and merged with SORTAV
 R. H. Blessing, Cryst. Rev., 1987, 1, 3
 R. H. Blessing, J. Appl. Cryst., 1989, 22, 396
;
_diffrn_reflns_theta_full        32.77
_diffrn_reflns_theta_max         27.51
_diffrn_reflns_theta_min         2.40
_diffrn_source                   'rotating-anode X-ray source'
_exptl_absorpt_coefficient_mu    0.231
_exptl_absorpt_correction_T_max  0.7454
_exptl_absorpt_correction_T_min  0.4508
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
 R. H. Blessing, Acta Cryst., 1995, A51, 33
;
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.221
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       unspecified
_exptl_crystal_F_000             244
_exptl_crystal_preparation       Luminescent
_exptl_crystal_recrystallization_method
'Re-crystallisation from solvent: acetone'
_exptl_crystal_size_max          0.15
_exptl_crystal_size_mid          0.12
_exptl_crystal_size_min          0.10
_refine_diff_density_max         0.892
_refine_diff_density_min         -0.492
_refine_diff_density_rms         0.089
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.122
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     154
_refine_ls_number_reflns         3992
_refine_ls_number_restraints     2
_refine_ls_restrained_S_all      1.127
_refine_ls_R_factor_all          0.0803
_refine_ls_R_factor_gt           0.0598
_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)+(0.1102P)²+0.1767P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1795
_refine_ls_wR_factor_ref         0.1889
_reflns_number_gt                2948
_reflns_number_total             2992
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            1000006.cif
_cod_data_source_block           PCOD1000006
_cod_depositor_comments
;
The following automatic conversions were performed:

data item '_diffrn_radiation_probe' value 'X-ray' was changed to
'x-ray' in accordance with the built-in table derived from the CIF
Core dictionary named 'cif_core.dic' version 2.4.5 last updated on
2014-11-21.

Automatic conversion script
Id: cif_fix_values 6909 2019-04-08 15:41:33Z antanas 
;
_cod_original_sg_symbol_Hall     -P1
_cod_original_sg_symbol_H-M      P-1
_cod_database_code               7234043
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
_atom_site_disorder_assembly
_atom_site_disorder_group
S1 S 0.35362(7) 0.74515(7) 0.22520(5) 0.02567(18) Uani 1 1 d U . .
O1 O 0.49956(19) 1.14046(18) 0.24997(15) 0.0211(3) Uani 1 1 d . . .
N1 N 0.1955(2) 1.0320(2) 0.30250(16) 0.0172(3) Uani 1 1 d . . .
C1 C 0.4268(2) 0.8877(2) 0.36896(19) 0.0164(3) Uani 1 1 d U . .
C13 C 0.1994(3) 1.1241(2) 0.19978(19) 0.0171(4) Uani 1 1 d . . .
C3 C 0.5150(3) 0.6863(2) 0.4546(2) 0.0164(4) Uani 1 1 d U . .
H3 H 0.5675 0.6357 0.5211 0.020 Uiso 1 1 calc R . .
C2 C 0.5090(3) 0.8429(2) 0.4865(2) 0.0168(4) Uani 1 1 d . . .
B1 B 0.4114(3) 1.0514(3) 0.3623(2) 0.0170(4) Uani 1 1 d . . .
C8 C 0.0433(3) 1.1510(3) 0.1317(2) 0.0264(5) Uani 1 1 d . . .
C12 C 0.3786(3) 1.1862(2) 0.1701(2) 0.0200(4) Uani 1 1 d . . .
C5 C 0.0371(3) 0.9581(3) 0.3419(2) 0.0235(4) Uani 1 1 d . . .
H5 H 0.0331 0.8919 0.4128 0.028 Uiso 1 1 calc R . .
C11 C 0.4059(4) 1.2813(3) 0.0661(2) 0.0291(5) Uani 1 1 d . . .
H11 H 0.5250 1.3255 0.0421 0.035 Uiso 1 1 calc R . .
C4 C 0.4341(3) 0.6269(3) 0.3162(2) 0.0275(5) Uani 1 1 d U . .
H4 H 0.4240 0.5286 0.2749 0.033 Uiso 1 1 calc R . .
C6 C -0.1274(3) 0.9779(3) 0.2781(3) 0.0310(5) Uani 1 1 d . . .
H6 H -0.2421 0.9236 0.3060 0.037 Uiso 1 1 calc R . .
C7 C -0.1237(3) 1.0734(3) 0.1777(3) 0.0314(5) Uani 1 1 d . . .
H7 H -0.2345 1.0878 0.1382 0.038 Uiso 1 1 calc R . .
C9 C 0.0756(4) 1.2499(3) 0.0272(2) 0.0359(6) Uani 1 1 d . . .
H9 H -0.0231 1.2746 -0.0221 0.043 Uiso 1 1 calc R . .
C10 C 0.2521(4) 1.3107(3) -0.0034(2) 0.0360(6) Uani 1 1 d . . .
H10 H 0.2704 1.3760 -0.0752 0.043 Uiso 1 1 calc R . .
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'
S S 0.1246 0.1234 '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
C4 S1 C1 93.55(10) . .
C12 O1 B1 110.28(14) . .
C5 N1 C13 119.89(17) . .
C5 N1 B1 132.73(16) . .
C13 N1 B1 107.14(15) . .
C2 C1 B1 125.39(18) . .
C2 C1 S1 110.73(14) . .
B1 C1 S1 123.78(14) . .
N1 C13 C12 110.69(16) . .
N1 C13 C8 124.23(19) . .
C12 C13 C8 125.07(19) . .
C4 C3 C2 110.17(16) . .
C4 C3 H3 124.9 . .
C2 C3 H3 124.9 . .
C1 C2 C3 112.02(17) . .
C1 C2 B1 122.98(17) . 2_676
C3 C2 B1 125.00(16) . 2_676
O1 B1 C1 113.05(15) . .
O1 B1 C2 112.37(16) . 2_676
C1 B1 C2 111.50(15) . 2_676
O1 B1 N1 98.28(13) . .
C1 B1 N1 112.94(16) . .
C2 B1 N1 107.95(14) 2_676 .
C13 C8 C9 115.7(2) . .
C13 C8 C7 114.9(2) . .
C9 C8 C7 129.5(2) . .
O1 C12 C11 129.54(19) . .
O1 C12 C13 112.33(16) . .
C11 C12 C13 118.13(19) . .
N1 C5 C6 119.6(2) . .
N1 C5 H5 120.2 . .
C6 C5 H5 120.2 . .
C12 C11 C10 118.0(2) . .
C12 C11 H11 121.0 . .
C10 C11 H11 121.0 . .
C3 C4 S1 113.52(16) . .
C3 C4 H4 123.2 . .
S1 C4 H4 123.2 . .
C7 C6 C5 121.0(2) . .
C7 C6 H6 119.5 . .
C5 C6 H6 119.5 . .
C6 C7 C8 120.43(19) . .
C6 C7 H7 119.8 . .
C8 C7 H7 119.8 . .
C10 C9 C8 119.5(2) . .
C10 C9 H9 120.2 . .
C8 C9 H9 120.2 . .
C9 C10 C11 123.6(2) . .
C9 C10 H10 118.2 . .
C11 C10 H10 118.2 . .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
S1 C4 1.689(2) .
S1 C1 1.722(2) .
O1 C12 1.333(2) .
O1 B1 1.526(3) .
N1 C5 1.315(3) .
N1 C13 1.355(2) .
N1 B1 1.626(2) .
C1 C2 1.378(2) .
C1 B1 1.582(3) .
C13 C12 1.400(3) .
C13 C8 1.405(3) .
C3 C4 1.363(3) .
C3 C2 1.499(3) .
C3 H3 0.9500 .
C2 B1 1.598(3) 2_676
B1 C2 1.598(3) 2_676
C8 C9 1.407(3) .
C8 C7 1.409(4) .
C12 C11 1.378(3) .
C5 C6 1.415(3) .
C5 H5 0.9500 .
C11 C10 1.407(3) .
C11 H11 0.9500 .
C4 H4 0.9500 .
C6 C7 1.358(4) .
C6 H6 0.9500 .
C7 H7 0.9500 .
C9 C10 1.385(4) .
C9 H9 0.9500 .
C10 H10 0.9500 .
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_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
C4 S1 C1 C2 -1.22(16) . . . .
C4 S1 C1 B1 175.38(17) . . . .
C5 N1 C13 C12 -177.60(18) . . . .
B1 N1 C13 C12 7.3(2) . . . .
C5 N1 C13 C8 1.6(3) . . . .
B1 N1 C13 C8 -173.53(18) . . . .
B1 C1 C2 C3 -175.15(16) . . . .
S1 C1 C2 C3 1.4(2) . . . .
B1 C1 C2 B1 4.4(3) . . . 2_676
S1 C1 C2 B1 -179.03(14) . . . 2_676
C4 C3 C2 C1 -0.9(2) . . . .
C4 C3 C2 B1 179.54(18) . . . 2_676
C12 O1 B1 C1 129.78(17) . . . .
C12 O1 B1 C2 -102.93(18) . . . 2_676
C12 O1 B1 N1 10.44(19) . . . .
C2 C1 B1 O1 123.8(2) . . . .
S1 C1 B1 O1 -52.3(2) . . . .
C2 C1 B1 C2 -4.0(3) . . . 2_676
S1 C1 B1 C2 179.91(13) . . . 2_676
C2 C1 B1 N1 -125.75(19) . . . .
S1 C1 B1 N1 58.1(2) . . . .
C5 N1 B1 O1 175.3(2) . . . .
C13 N1 B1 O1 -10.45(19) . . . .
C5 N1 B1 C1 55.9(3) . . . .
C13 N1 B1 C1 -129.88(17) . . . .
C5 N1 B1 C2 -67.8(3) . . . 2_676
C13 N1 B1 C2 106.39(17) . . . 2_676
N1 C13 C8 C9 -179.69(19) . . . .
C12 C13 C8 C9 -0.6(3) . . . .
N1 C13 C8 C7 -0.2(3) . . . .
C12 C13 C8 C7 178.81(19) . . . .
B1 O1 C12 C11 173.3(2) . . . .
B1 O1 C12 C13 -7.4(2) . . . .
N1 C13 C12 O1 -0.4(2) . . . .
C8 C13 C12 O1 -179.53(18) . . . .
N1 C13 C12 C11 179.09(18) . . . .
C8 C13 C12 C11 -0.1(3) . . . .
C13 N1 C5 C6 -1.1(3) . . . .
B1 N1 C5 C6 172.54(19) . . . .
O1 C12 C11 C10 179.7(2) . . . .
C13 C12 C11 C10 0.3(3) . . . .
C2 C3 C4 S1 0.0(2) . . . .
C1 S1 C4 C3 0.72(18) . . . .
N1 C5 C6 C7 -0.7(3) . . . .
C5 C6 C7 C8 2.0(3) . . . .
C13 C8 C7 C6 -1.5(3) . . . .
C9 C8 C7 C6 177.8(2) . . . .
C13 C8 C9 C10 1.1(3) . . . .
C7 C8 C9 C10 -178.3(2) . . . .
C8 C9 C10 C11 -0.9(4) . . . .
C12 C11 C10 C9 0.1(4) . . . .
