#------------------------------------------------------------------------------
#$Date: 2019-09-23 10:34:52 +0300 (Mon, 23 Sep 2019) $
#$Revision: 218694 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/23/40/7234039.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_7234039
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'
_chemical_formula_sum            'C30 H18 B2 F2 N2 O2'
_chemical_formula_weight         498.08
_chemical_melting_point          368.9
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_atom_sites_solution_hydrogens   geom
_audit_creation_method           SHELXL-97
_cell_angle_alpha                90.027(3)
_cell_angle_beta                 96.603(3)
_cell_angle_gamma                113.011(3)
_cell_formula_units_Z            2
_cell_length_a                   10.3718(6)
_cell_length_b                   10.6554(6)
_cell_length_c                   11.3670(6)
_cell_measurement_reflns_used    11865
_cell_measurement_temperature    100(1)
_cell_measurement_theta_max      32.7328
_cell_measurement_theta_min      1.7363
_cell_volume                     1147.19(11)
_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(1)
_diffrn_detector                 'APEXII CCD camera'
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.994
_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  0.0411
_diffrn_reflns_av_unetI/netI     0.0547
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.994
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            35016
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.994
_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        25.242
_diffrn_reflns_theta_max         34.706
_diffrn_reflns_theta_min         1.806
_diffrn_source                   'rotating-anode X-ray source'
_exptl_absorpt_coefficient_mu    0.101
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.97884
_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    1.442
_exptl_crystal_description       cubic
_exptl_crystal_F_000             512
_exptl_crystal_preparation       Luminescent
_exptl_crystal_recrystallization_method
'Re-crystallisation from solvent: acetone'
_exptl_crystal_size_max          0.10
_exptl_crystal_size_mid          0.10
_exptl_crystal_size_min          0.07
_refine_diff_density_max         0.627
_refine_diff_density_min         -0.295
_refine_diff_density_rms         0.069
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.023
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     362
_refine_ls_number_reflns         9824
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.023
_refine_ls_R_factor_all          0.0906
_refine_ls_R_factor_gt           0.0557
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.0696P)²+0.3673P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1328
_refine_ls_wR_factor_ref         0.1484
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                6804
_reflns_number_total             9824
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            1000002.cif
_cod_data_source_block           PCOD1000002
_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        1147.18(11)
_cod_database_code               7234039
_shelx_space_group_comment
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_shelxl_version_number           2013-4
loop_
_space_group_symop_operation_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_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
F1A F 0.66697(9) 0.09834(8) 0.27160(8) 0.0161(2) Uani 0.867(2) 1 d . . P A 1
C3A C 0.79352(13) 0.20473(12) 0.28473(10) 0.0144(2) Uani 0.867(2) 1 d . . P A 1
C6A C 1.05414(13) 0.40836(14) 0.30412(12) 0.0175(2) Uani 0.867(2) 1 d . . P A 1
H6A H 1.1456 0.4793 0.3087 0.021 Uiso 0.867(2) 1 calc R U P A 1
F2A F 0.97554(10) 0.86858(9) 0.35603(9) 0.0219(2) Uani 0.867(2) 1 d . . P A 1
C9A C 0.85053(13) 0.75892(12) 0.36362(11) 0.0159(2) Uani 0.867(2) 1 d . . P A 1
C12A C 0.59407(13) 0.55327(13) 0.37145(12) 0.0171(2) Uani 0.867(2) 1 d . . P A
1
H12A H 0.5036 0.4823 0.3730 0.021 Uiso 0.867(2) 1 calc R U P A 1
F1B F 1.1729(6) 0.4754(7) 0.2969(6) 0.0251(16) Uani 0.133(2) 1 d . . P A 2
C3B C 0.79352(13) 0.20473(12) 0.28473(10) 0.0144(2) Uani 0.133(2) 1 d . . P A 2
H3B H 0.7028 0.1322 0.2747 0.017 Uiso 0.133(2) 1 calc R U P A 2
C6B C 1.05414(13) 0.40836(14) 0.30412(12) 0.0175(2) Uani 0.133(2) 1 d . . P A 2
C12B C 0.59407(13) 0.55327(13) 0.37145(12) 0.0171(2) Uani 0.133(2) 1 d . . P A
2
C9B C 0.85053(13) 0.75892(12) 0.36362(11) 0.0159(2) Uani 0.133(2) 1 d . . P A 2
H9B H 0.9387 0.8322 0.3588 0.019 Uiso 0.133(2) 1 calc R U P A 2
F2B F 0.4519(6) 0.4687(6) 0.3446(6) 0.0216(15) Uani 0.133(2) 1 d . . P A 2
O2 O 0.95457(9) 0.62891(9) 0.13371(7) 0.01356(17) Uani 1 1 d . . . . .
N2 N 1.10915(10) 0.69824(10) 0.31528(9) 0.01101(18) Uani 1 1 d . . . . .
O1 O 0.53515(9) 0.27023(9) 0.31102(8) 0.01460(17) Uani 1 1 d . . . . .
N1 N 0.59827(10) 0.36483(10) 0.12450(9) 0.01211(18) Uani 1 1 d . . . . .
C30 C 1.17696(12) 0.75613(11) 0.22177(10) 0.01067(19) Uani 1 1 d . . . . .
C2 C 0.79930(12) 0.33660(11) 0.27697(10) 0.01075(19) Uani 1 1 d . . . . .
C7 C 0.69735(12) 0.52486(12) 0.32098(10) 0.0119(2) Uani 1 1 d . . . . .
C21 C 0.45972(12) 0.28032(12) 0.11602(11) 0.0134(2) Uani 1 1 d . . . . .
C1 C 0.93592(12) 0.44198(12) 0.28418(10) 0.0114(2) Uani 1 1 d . . . . .
C25 C 1.31941(12) 0.84358(11) 0.23065(10) 0.0120(2) Uani 1 1 d . . . . .
C29 C 1.08454(12) 0.71440(11) 0.11538(10) 0.0116(2) Uani 1 1 d . . . . .
C22 C 1.17896(13) 0.72353(12) 0.42356(10) 0.0134(2) Uani 1 1 d . . . . .
H22 H 1.1318 0.6831 0.4893 0.016 Uiso 1 1 calc R U . . .
C8 C 0.83210(12) 0.63085(12) 0.31869(10) 0.0117(2) Uani 1 1 d . . . . .
C27 C 1.27981(14) 0.85525(13) 0.01861(11) 0.0164(2) Uani 1 1 d . . . . .
H27 H 1.3158 0.8911 -0.0528 0.020 Uiso 1 1 calc R U . . .
C20 C 0.42388(12) 0.22716(12) 0.22657(11) 0.0137(2) Uani 1 1 d . . . . .
C28 C 1.13566(13) 0.76448(12) 0.01146(10) 0.0144(2) Uani 1 1 d . . . . .
H28 H 1.0769 0.7394 -0.0624 0.017 Uiso 1 1 calc R U . . .
C13 C 0.65190(13) 0.42266(12) 0.02821(11) 0.0143(2) Uani 1 1 d . . . . .
H13 H 0.7487 0.4820 0.0332 0.017 Uiso 1 1 calc R U . . .
C14 C 0.56535(14) 0.39607(13) -0.08141(11) 0.0168(2) Uani 1 1 d . . . . .
H14 H 0.6050 0.4368 -0.1502 0.020 Uiso 1 1 calc R U . . .
C19 C 0.28589(13) 0.14181(13) 0.23385(13) 0.0174(2) Uani 1 1 d . . . . .
H19 H 0.2571 0.1033 0.3066 0.021 Uiso 1 1 calc R U . . .
C23 C 1.32292(13) 0.81027(12) 0.44125(11) 0.0149(2) Uani 1 1 d . . . . .
H23 H 1.3726 0.8284 0.5191 0.018 Uiso 1 1 calc R U . . .
C15 C 0.42443(14) 0.31214(13) -0.09052(12) 0.0179(2) Uani 1 1 d . . . . .
H15 H 0.3670 0.2955 -0.1649 0.021 Uiso 1 1 calc R U . . .
B1 B 0.66327(13) 0.37524(13) 0.26411(12) 0.0120(2) Uani 1 1 d . . . . .
C16 C 0.36552(13) 0.25073(13) 0.01140(12) 0.0157(2) Uani 1 1 d . . . . .
B2 B 0.95200(13) 0.59713(13) 0.26527(12) 0.0118(2) Uani 1 1 d . . . . .
C26 C 1.37036(13) 0.89434(12) 0.12230(11) 0.0153(2) Uani 1 1 d . . . . .
H26 H 1.4661 0.9547 0.1216 0.018 Uiso 1 1 calc R U . . .
C4 C 0.90941(15) 0.17012(13) 0.30599(11) 0.0189(2) Uani 1 1 d . . . . .
H4 H 0.8981 0.0776 0.3125 0.023 Uiso 1 1 calc R U . A 1
C10 C 0.74991(15) 0.78724(13) 0.41477(12) 0.0189(2) Uani 1 1 d . . . . .
H10 H 0.7694 0.8764 0.4459 0.023 Uiso 1 1 calc R U . A 1
C24 C 1.39256(13) 0.86927(12) 0.34643(11) 0.0147(2) Uani 1 1 d . . . . .
H24 H 1.4900 0.9273 0.3591 0.018 Uiso 1 1 calc R U . . .
C11 C 0.61991(14) 0.68208(14) 0.41939(12) 0.0192(2) Uani 1 1 d . . . . .
H11 H 0.5488 0.6978 0.4551 0.023 Uiso 1 1 calc R U . A 1
C17 C 0.22332(14) 0.16358(14) 0.02177(13) 0.0213(3) Uani 1 1 d . . . . .
H17 H 0.1535 0.1407 -0.0455 0.026 Uiso 1 1 calc R U . . .
C5 C 1.04212(15) 0.27465(14) 0.31738(12) 0.0202(3) Uani 1 1 d . . . . .
H5 H 1.1242 0.2553 0.3341 0.024 Uiso 1 1 calc R U . A 1
C18 C 0.18771(14) 0.11290(14) 0.12931(14) 0.0219(3) Uani 1 1 d . . . . .
H18 H 0.0920 0.0552 0.1344 0.026 Uiso 1 1 calc R U . . .
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'
F F 0.0171 0.0103 '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 115.17(11) . .
F1A C3A C2 119.57(11) . .
C4 C3A C2 125.26(12) . .
C5 C6A C1 122.24(12) . .
C5 C6A H6A 118.9 . .
C1 C6A H6A 118.9 . .
F2A C9A C10 115.72(11) . .
F2A C9A C8 119.59(11) . .
C10 C9A C8 124.68(12) . .
C11 C12A C7 122.04(12) . .
C11 C12A H12A 119.0 . .
C7 C12A H12A 119.0 . .
C29 O2 B2 109.94(9) . .
C22 N2 C30 119.82(10) . .
C22 N2 B2 131.95(10) . .
C30 N2 B2 108.04(9) . .
C20 O1 B1 110.61(9) . .
C13 N1 C21 119.33(11) . .
C13 N1 B1 133.58(10) . .
C21 N1 B1 107.06(9) . .
N2 C30 C25 124.30(11) . .
N2 C30 C29 110.60(10) . .
C25 C30 C29 125.09(10) . .
C3A C2 C1 116.14(10) . .
C3A C2 B1 124.37(10) . .
C1 C2 B1 119.47(10) . .
C12A C7 C8 118.90(11) . .
C12A C7 B1 120.85(11) . .
C8 C7 B1 120.24(10) . .
N1 C21 C16 124.41(11) . .
N1 C21 C20 110.79(11) . .
C16 C21 C20 124.79(11) . .
C6A C1 C2 119.13(11) . .
C6A C1 B2 121.48(10) . .
C2 C1 B2 119.37(10) . .
C30 C25 C24 115.28(10) . .
C30 C25 C26 115.68(11) . .
C24 C25 C26 129.04(11) . .
O2 C29 C28 129.64(11) . .
O2 C29 C30 111.95(10) . .
C28 C29 C30 118.41(11) . .
N2 C22 C23 119.97(10) . .
N2 C22 H22 120.0 . .
C23 C22 H22 120.0 . .
C9A C8 C7 116.68(10) . .
C9A C8 B2 124.40(10) . .
C7 C8 B2 118.93(10) . .
C26 C27 C28 124.06(11) . .
C26 C27 H27 118.0 . .
C28 C27 H27 118.0 . .
O1 C20 C19 129.63(12) . .
O1 C20 C21 112.24(10) . .
C19 C20 C21 118.13(12) . .
C29 C28 C27 117.45(11) . .
C29 C28 H28 121.3 . .
C27 C28 H28 121.3 . .
N1 C13 C14 120.03(11) . .
N1 C13 H13 120.0 . .
C14 C13 H13 120.0 . .
C15 C14 C13 121.04(12) . .
C15 C14 H14 119.5 . .
C13 C14 H14 119.5 . .
C20 C19 C18 118.03(12) . .
C20 C19 H19 121.0 . .
C18 C19 H19 121.0 . .
C24 C23 C22 120.48(11) . .
C24 C23 H23 119.8 . .
C22 C23 H23 119.8 . .
C14 C15 C16 119.59(12) . .
C14 C15 H15 120.2 . .
C16 C15 H15 120.2 . .
O1 B1 C2 114.10(10) . .
O1 B1 C7 110.34(9) . .
C2 B1 C7 112.63(10) . .
O1 B1 N1 98.81(9) . .
C2 B1 N1 110.36(9) . .
C7 B1 N1 109.73(9) . .
C21 C16 C15 115.57(11) . .
C21 C16 C17 115.87(12) . .
C15 C16 C17 128.56(12) . .
O2 B2 N2 99.14(8) . .
O2 B2 C8 110.83(10) . .
N2 B2 C8 113.79(9) . .
O2 B2 C1 110.75(9) . .
N2 B2 C1 108.94(9) . .
C8 B2 C1 112.62(9) . .
C27 C26 C25 119.29(11) . .
C27 C26 H26 120.4 . .
C25 C26 H26 120.4 . .
C5 C4 C3A 117.82(12) . .
C5 C4 H4 121.1 . .
C3A C4 H4 121.1 . .
C9A C10 C11 118.09(12) . .
C9A C10 H10 121.0 . .
C11 C10 H10 121.0 . .
C23 C24 C25 120.16(11) . .
C23 C24 H24 119.9 . .
C25 C24 H24 119.9 . .
C10 C11 C12A 119.53(11) . .
C10 C11 H11 120.2 . .
C12A C11 H11 120.2 . .
C18 C17 C16 119.51(13) . .
C18 C17 H17 120.2 . .
C16 C17 H17 120.2 . .
C4 C5 C6A 119.26(12) . .
C4 C5 H5 120.4 . .
C6A C5 H5 120.4 . .
C17 C18 C19 123.64(12) . .
C17 C18 H18 118.2 . .
C19 C18 H18 118.2 . .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
F1A C3A 1.3496(14) .
C3A C4 1.3852(18) .
C3A C2 1.3861(16) .
C6A C5 1.3906(19) .
C6A C1 1.4010(17) .
C6A H6A 0.9500 .
F2A C9A 1.3767(15) .
C9A C10 1.3799(18) .
C9A C8 1.3901(17) .
C12A C11 1.3895(18) .
C12A C7 1.4010(16) .
C12A H12A 0.9500 .
O2 C29 1.3398(14) .
O2 B2 1.5344(16) .
N2 C22 1.3244(15) .
N2 C30 1.3559(14) .
N2 B2 1.5981(16) .
O1 C20 1.3396(15) .
O1 B1 1.5176(15) .
N1 C13 1.3265(15) .
N1 C21 1.3570(15) .
N1 B1 1.6372(17) .
C30 C25 1.3966(16) .
C30 C29 1.4067(16) .
C2 C1 1.4158(16) .
C2 B1 1.6088(17) .
C7 C8 1.4155(16) .
C7 B1 1.6095(18) .
C21 C16 1.3999(17) .
C21 C20 1.4077(17) .
C1 B2 1.6125(18) .
C25 C24 1.4107(17) .
C25 C26 1.4197(16) .
C29 C28 1.3728(16) .
C22 C23 1.4057(17) .
C22 H22 0.9500 .
C8 B2 1.6023(17) .
C27 C26 1.3726(18) .
C27 C28 1.4209(17) .
C27 H27 0.9500 .
C20 C19 1.3754(17) .
C28 H28 0.9500 .
C13 C14 1.4080(17) .
C13 H13 0.9500 .
C14 C15 1.3747(19) .
C14 H14 0.9500 .
C19 C18 1.421(2) .
C19 H19 0.9500 .
C23 C24 1.3796(17) .
C23 H23 0.9500 .
C15 C16 1.4124(19) .
C15 H15 0.9500 .
C16 C17 1.4215(18) .
C26 H26 0.9500 .
C4 C5 1.383(2) .
C4 H4 0.9500 .
C10 C11 1.3825(19) .
C10 H10 0.9500 .
C24 H24 0.9500 .
C11 H11 0.9500 .
C17 C18 1.368(2) .
C17 H17 0.9500 .
C5 H5 0.9500 .
C18 H18 0.9500 .
