#------------------------------------------------------------------------------
#$Date: 2019-09-23 10:34:59 +0300 (Mon, 23 Sep 2019) $
#$Revision: 218695 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/23/40/7234040.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_7234040
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         'C30 H18 B2 F2 N2 O2, 2(C H Cl3)'
_chemical_formula_sum            'C32 H20 B2 Cl6 F2 N2 O2'
_chemical_formula_weight         736.82
_chemical_melting_point          368.9
_chemical_name_systematic
;
 1,6-Difluoro-5,10-bis(8-oxyquinolinato)-5,10-dihydroboranthrene
;
_space_group_IT_number           14
_space_group_name_Hall           '-P 2ybc'
_space_group_name_H-M_alt        'P 1 21/c 1'
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2ybc'
_symmetry_space_group_name_H-M   'P 1 21/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                 107.299(3)
_cell_angle_gamma                90.00
_cell_formula_units_Z            2
_cell_length_a                   9.5314(2)
_cell_length_b                   14.0687(3)
_cell_length_c                   12.3085(3)
_cell_measurement_reflns_used    14321
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      32.6156
_cell_measurement_theta_min      1.7294
_cell_volume                     1575.84(7)
_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  0.0314
_diffrn_reflns_av_sigmaI/netI    0.0242
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       21
_diffrn_reflns_limit_k_min       -21
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            37161
_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        32.69
_diffrn_reflns_theta_max         32.69
_diffrn_reflns_theta_min         2.24
_diffrn_source                   'rotating-anode X-ray source'
_exptl_absorpt_coefficient_mu    0.593
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.90424
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.20 (release 27-06-2012 CrysAlis171 .NET)
(compiled Jul 11 2012,15:38:31)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.553
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       cubic
_exptl_crystal_F_000             744
_exptl_crystal_preparation       Luminescent
_exptl_crystal_recrystallization_method
'Re-crystallisation from solvent: CHCl3'
_exptl_crystal_size_max          0.15
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.15
_refine_diff_density_max         1.291
_refine_diff_density_min         -1.365
_refine_diff_density_rms         0.071
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.035
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     218
_refine_ls_number_reflns         5560
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.038
_refine_ls_R_factor_all          0.0618
_refine_ls_R_factor_gt           0.0450
_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)+(0.0362P)²+1.5530P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1007
_refine_ls_wR_factor_ref         0.1099
_reflns_number_gt                4366
_reflns_number_total             5560
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            1000003.cif
_cod_data_source_block           PCOD1000003
_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_cell_volume        1575.84(6)
_cod_original_sg_symbol_Hall     -P2ybc
_cod_original_sg_symbol_H-M      P2(1)/c
_cod_database_code               7234040
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -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
F1A F 0.66767(15) -0.03457(10) 0.81578(11) 0.0235(3) Uani 0.700(3) 1 d PU A 1
C3A C 0.71140(18) -0.01681(11) 0.72641(12) 0.0216(3) Uani 0.700(3) 1 d PU A 1
C6A C 0.81787(17) 0.02663(11) 0.55152(15) 0.0236(3) Uani 0.700(3) 1 d P A 1
H6A H 0.8558 0.0422 0.4906 0.028 Uiso 0.700(3) 1 calc PR A 1
F1B F 0.8818(3) 0.0514(3) 0.4838(3) 0.0265(9) Uani 0.300(3) 1 d P A 2
C3B C 0.71140(18) -0.01681(11) 0.72641(12) 0.0216(3) Uani 0.300(3) 1 d P A 2
H3B H 0.6751 -0.0319 0.7883 0.026 Uiso 0.300(3) 1 calc PR A 2
C6B C 0.81787(17) 0.02663(11) 0.55152(15) 0.0236(3) Uani 0.300(3) 1 d P A 2
C19 C 0.16488(18) 0.28489(12) 0.05149(14) 0.0248(3) Uani 1 1 d . . .
H19 H 0.1825 0.3550 0.0519 0.030 Uiso 1 1 calc R . .
Cl1 Cl 0.32498(5) 0.22630(4) 0.04501(4) 0.03658(12) Uani 1 1 d . . .
Cl3 Cl 0.12417(5) 0.25474(3) 0.17680(4) 0.03408(11) Uani 1 1 d . . .
Cl2 Cl 0.01642(6) 0.25720(6) -0.06755(5) 0.05821(19) Uani 1 1 d . . .
O1 O 0.38591(12) 0.04645(7) 0.67907(9) 0.0182(2) Uani 1 1 d . . .
N1 N 0.40457(13) -0.12166(8) 0.65583(10) 0.0155(2) Uani 1 1 d . . .
C12 C 0.31973(17) -0.26511(11) 0.77875(13) 0.0224(3) Uani 1 1 d . . .
H12 H 0.2900 -0.3152 0.8188 0.027 Uiso 1 1 calc R . .
C2 C 0.60986(15) -0.00925(9) 0.61836(11) 0.0152(2) Uani 1 1 d . . .
C1 C 0.66612(15) 0.01306(9) 0.52753(12) 0.0154(2) Uani 1 1 d . . .
C7 C 0.34147(15) -0.00223(10) 0.75659(12) 0.0173(2) Uani 1 1 d . . .
C15 C 0.34851(15) -0.10123(10) 0.74213(11) 0.0156(2) Uani 1 1 d . . .
C8 C 0.29274(17) 0.03108(12) 0.84394(13) 0.0225(3) Uani 1 1 d . . .
H8 H 0.2889 0.0973 0.8579 0.027 Uiso 1 1 calc R . .
B1 B 0.43743(17) -0.02149(11) 0.60117(13) 0.0154(3) Uani 1 1 d . . .
C14 C 0.42127(16) -0.21179(10) 0.63059(13) 0.0190(3) Uani 1 1 d . . .
H14 H 0.4621 -0.2268 0.5710 0.023 Uiso 1 1 calc R . .
C10 C 0.25048(17) -0.13328(13) 0.89632(13) 0.0247(3) Uani 1 1 d . . .
H10 H 0.2168 -0.1755 0.9434 0.030 Uiso 1 1 calc R . .
C11 C 0.30377(15) -0.16931(11) 0.80804(12) 0.0188(3) Uani 1 1 d . . .
C5 C 0.91498(17) 0.01844(12) 0.65966(16) 0.0277(3) Uani 1 1 d . . .
H5 H 1.0173 0.0280 0.6724 0.033 Uiso 1 1 calc R A 1
C13 C 0.37870(17) -0.28545(11) 0.69173(13) 0.0222(3) Uani 1 1 d . . .
H13 H 0.3907 -0.3498 0.6728 0.027 Uiso 1 1 calc R . .
C9 C 0.24828(17) -0.03682(13) 0.91265(13) 0.0257(3) Uani 1 1 d . . .
H9 H 0.2151 -0.0141 0.9734 0.031 Uiso 1 1 calc R . .
C4 C 0.86072(18) -0.00387(12) 0.74921(14) 0.0276(3) Uani 1 1 d . A .
H4 H 0.9249 -0.0101 0.8245 0.033 Uiso 1 1 calc R B 1
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'
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'
F F 0.0171 0.0103 '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
F1A C3A C4 114.90(14) . .
F1A C3A C2 120.68(15) . .
C4 C3A C2 124.40(15) . .
C5 C6A C1 123.08(16) . .
C5 C6A H6A 118.5 . .
C1 C6A H6A 118.5 . .
Cl3 C19 Cl2 110.34(9) . .
Cl3 C19 Cl1 110.45(9) . .
Cl2 C19 Cl1 110.75(9) . .
Cl3 C19 H19 108.4 . .
Cl2 C19 H19 108.4 . .
Cl1 C19 H19 108.4 . .
C7 O1 B1 110.73(11) . .
C14 N1 C15 119.30(12) . .
C14 N1 B1 132.69(12) . .
C15 N1 B1 108.00(11) . .
C13 C12 C11 119.66(13) . .
C13 C12 H12 120.2 . .
C11 C12 H12 120.2 . .
C3A C2 C1 116.88(13) . .
C3A C2 B1 120.70(13) . .
C1 C2 B1 122.37(12) . .
C6A C1 C2 118.36(13) . .
C6A C1 B1 119.49(13) . 3_656
C2 C1 B1 122.14(12) . 3_656
O1 C7 C8 129.36(14) . .
O1 C7 C15 112.21(12) . .
C8 C7 C15 118.43(14) . .
N1 C15 C11 124.62(13) . .
N1 C15 C7 110.72(12) . .
C11 C15 C7 124.66(13) . .
C7 C8 C9 117.79(15) . .
C7 C8 H8 121.1 . .
C9 C8 H8 121.1 . .
O1 B1 C1 110.74(11) . 3_656
O1 B1 C2 110.90(11) . .
C1 B1 C2 115.38(11) 3_656 .
O1 B1 N1 98.28(10) . .
C1 B1 N1 109.53(11) 3_656 .
C2 B1 N1 110.69(11) . .
N1 C14 C13 120.28(14) . .
N1 C14 H14 119.9 . .
C13 C14 H14 119.9 . .
C9 C10 C11 119.24(14) . .
C9 C10 H10 120.4 . .
C11 C10 H10 120.4 . .
C15 C11 C12 115.42(14) . .
C15 C11 C10 115.97(14) . .
C12 C11 C10 128.60(14) . .
C6A C5 C4 118.92(15) . .
C6A C5 H5 120.5 . .
C4 C5 H5 120.5 . .
C12 C13 C14 120.70(14) . .
C12 C13 H13 119.7 . .
C14 C13 H13 119.7 . .
C10 C9 C8 123.85(14) . .
C10 C9 H9 118.1 . .
C8 C9 H9 118.1 . .
C3A C4 C5 118.36(14) . .
C3A C4 H4 120.8 . .
C5 C4 H4 120.8 . .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
F1A C3A 1.311(2) .
C3A C4 1.378(2) .
C3A C2 1.3969(19) .
C6A C5 1.382(2) .
C6A C1 1.401(2) .
C6A H6A 0.9500 .
C19 Cl3 1.7508(17) .
C19 Cl2 1.7516(18) .
C19 Cl1 1.7569(17) .
C19 H19 1.0000 .
O1 C7 1.3414(17) .
O1 B1 1.5344(18) .
N1 C14 1.3262(18) .
N1 C15 1.3543(18) .
N1 B1 1.6316(19) .
C12 C13 1.380(2) .
C12 C11 1.415(2) .
C12 H12 0.9500 .
C2 C1 1.4116(19) .
C2 B1 1.603(2) .
C1 B1 1.602(2) 3_656
C7 C8 1.374(2) .
C7 C15 1.4083(19) .
C15 C11 1.4010(19) .
C8 C9 1.421(2) .
C8 H8 0.9500 .
B1 C1 1.602(2) 3_656
C14 C13 1.409(2) .
C14 H14 0.9500 .
C10 C9 1.373(3) .
C10 C11 1.423(2) .
C10 H10 0.9500 .
C5 C4 1.386(3) .
C5 H5 0.9500 .
C13 H13 0.9500 .
C9 H9 0.9500 .
C4 H4 0.9500 .
