#------------------------------------------------------------------------------
#$Date: 2019-09-23 10:35:08 +0300 (Mon, 23 Sep 2019) $
#$Revision: 218696 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/23/40/7234041.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_7234041
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 Cl2 N2 O2'
_chemical_formula_sum            'C30 H18 B2 Cl2 N2 O2'
_chemical_formula_weight         530.98
_chemical_melting_point          392.6
_chemical_name_systematic
;
 1,6-Dichloro-5,10-Bis(8-oxyquinolinato)-5,10-dihydroboranthrene
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2ybc'
_space_group_name_H-M_alt        'P 1 21/c 1'
_atom_sites_solution_hydrogens   geom
_cell_angle_alpha                90
_cell_angle_beta                 91.600(3)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   9.9401(3)
_cell_length_b                   12.5613(5)
_cell_length_c                   19.6590(8)
_cell_measurement_reflns_used    13623
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      35.6240
_cell_measurement_theta_min      2.0380
_cell_volume                     2453.68(16)
_computing_cell_refinement
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.31 (release 14-01-2014 CrysAlis171 .NET)
(compiled Jan 14 2014,18:38:05)
;
_computing_data_collection
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.31 (release 14-01-2014 CrysAlis171 .NET)
(compiled Jan 14 2014,18:38:05)
;
_computing_data_reduction
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.31 (release 14-01-2014 CrysAlis171 .NET)
(compiled Jan 14 2014,18:38:05)
;
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      100.01(10)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 8.0013
_diffrn_detector_type            Eos
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.969
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Single source at offset, Eos'
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0549
_diffrn_reflns_av_unetI/netI     0.0563
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.969
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_k_max       21
_diffrn_reflns_limit_k_min       -21
_diffrn_reflns_limit_l_max       33
_diffrn_reflns_limit_l_min       -33
_diffrn_reflns_number            61281
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.969
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         37.382
_diffrn_reflns_theta_min         1.924
_diffrn_source                   'SuperNova (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    0.298
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.86384
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.31 (release 14-01-2014 CrysAlis171 .NET)
(compiled Jan 14 2014,18:38:05)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.437
_exptl_crystal_description       cubic
_exptl_crystal_F_000             1088
_exptl_crystal_preparation       Luminescent
_exptl_crystal_recrystallization_method
'Re-crystallisation from solvent: acetone'
_exptl_crystal_size_max          0.05
_exptl_crystal_size_mid          0.04
_exptl_crystal_size_min          0.04
_refine_diff_density_max         2.227
_refine_diff_density_min         -0.508
_refine_diff_density_rms         0.098
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.036
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     343
_refine_ls_number_reflns         12402
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.036
_refine_ls_R_factor_all          0.1225
_refine_ls_R_factor_gt           0.0747
_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)+(0.0993P)²+1.8644P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1931
_refine_ls_wR_factor_ref         0.2238
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                7705
_reflns_number_total             12402
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            1000004.cif
_cod_data_source_block           PCOD1000004
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               7234041
_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+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_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
C1 C 0.14332(17) 0.13775(14) 0.33704(9) 0.0201(3) Uani 1 1 d . . . . .
C2 C 0.22619(18) 0.05679(15) 0.31043(9) 0.0220(3) Uani 1 1 d . . . . .
C3 C 0.1669(2) -0.00785(17) 0.25950(10) 0.0273(4) Uani 1 1 d . . . . .
C4 C 0.0390(2) 0.0099(2) 0.23094(10) 0.0318(4) Uani 1 1 d . . . . .
H4 H 0.0044 -0.0343 0.1954 0.038 Uiso 1 1 calc R U . . .
C5 C -0.0363(2) 0.09315(19) 0.25545(11) 0.0300(4) Uani 1 1 d . . . . .
H5 H -0.1224 0.1083 0.2356 0.036 Uiso 1 1 calc R U . . .
C6 C 0.01338(18) 0.15483(16) 0.30907(10) 0.0245(3) Uani 1 1 d . . . . .
H6 H -0.0413 0.2094 0.3272 0.029 Uiso 1 1 calc R U . . .
C7 C 0.43808(17) 0.15404(15) 0.37424(9) 0.0217(3) Uani 1 1 d . . . . .
C8 C 0.35349(18) 0.22853(14) 0.40610(9) 0.0213(3) Uani 1 1 d . . . . .
C9 C 0.41773(19) 0.31130(15) 0.44149(10) 0.0245(3) Uani 1 1 d . . . . .
C10 C 0.5568(2) 0.32648(16) 0.44434(11) 0.0272(4) Uani 1 1 d . . . . .
H10 H 0.5953 0.3857 0.4677 0.033 Uiso 1 1 calc R U . . .
C11 C 0.6373(2) 0.25327(17) 0.41232(11) 0.0291(4) Uani 1 1 d . . . . .
H11 H 0.7324 0.2612 0.4140 0.035 Uiso 1 1 calc R U . . .
C12 C 0.57877(19) 0.16842(17) 0.37783(11) 0.0266(4) Uani 1 1 d . . . . .
H12 H 0.6349 0.1185 0.3560 0.032 Uiso 1 1 calc R U . . .
C13 C 0.19164(18) 0.05385(14) 0.49940(9) 0.0211(3) Uani 1 1 d . . . . .
H13 H 0.2584 0.0118 0.4785 0.025 Uiso 1 1 calc R U . . .
C14 C 0.13491(19) 0.02008(15) 0.56058(9) 0.0236(3) Uani 1 1 d . . . . .
H14 H 0.1633 -0.0453 0.5806 0.028 Uiso 1 1 calc R U . . .
C15 C 0.0390(2) 0.08030(16) 0.59183(9) 0.0251(3) Uani 1 1 d . . . . .
H15 H 0.0017 0.0565 0.6331 0.030 Uiso 1 1 calc R U . . .
C16 C -0.00405(19) 0.17787(15) 0.56239(9) 0.0232(3) Uani 1 1 d . . . . .
C17 C -0.0992(2) 0.25228(18) 0.58658(11) 0.0309(4) Uani 1 1 d . . . . .
H17 H -0.1452 0.2390 0.6274 0.037 Uiso 1 1 calc R U . . .
C18 C -0.1236(2) 0.34390(18) 0.54996(12) 0.0327(4) Uani 1 1 d . . . . .
H18 H -0.1870 0.3929 0.5672 0.039 Uiso 1 1 calc R U . . .
C19 C -0.06080(19) 0.37036(16) 0.48828(11) 0.0271(4) Uani 1 1 d . . . . .
H19 H -0.0813 0.4347 0.4648 0.033 Uiso 1 1 calc R U . . .
C20 C 0.03126(18) 0.29873(14) 0.46372(10) 0.0222(3) Uani 1 1 d . . . . .
C21 C 0.05704(17) 0.20516(14) 0.50124(9) 0.0200(3) Uani 1 1 d . . . . .
C22 C 0.5094(2) 0.0609(2) 0.22048(11) 0.0312(4) Uani 1 1 d . . . . .
H22 H 0.4601 0.1215 0.2051 0.037 Uiso 1 1 calc R U . . .
C23 C 0.6125(2) 0.0185(2) 0.18088(12) 0.0361(5) Uani 1 1 d . . . . .
H23 H 0.6306 0.0499 0.1381 0.043 Uiso 1 1 calc R U . . .
C24 C 0.6863(2) -0.0665(2) 0.20272(12) 0.0359(5) Uani 1 1 d . . . . .
H24 H 0.7557 -0.0937 0.1754 0.043 Uiso 1 1 calc R U . . .
C25 C 0.66008(19) -0.11458(18) 0.26630(11) 0.0305(4) Uani 1 1 d . . . . .
C26 C 0.7262(2) -0.20070(19) 0.29896(13) 0.0354(5) Uani 1 1 d . . . . .
H26 H 0.8003 -0.2344 0.2784 0.042 Uiso 1 1 calc R U . . .
C27 C 0.6824(2) -0.23534(18) 0.36098(14) 0.0373(5) Uani 1 1 d . . . . .
H27 H 0.7288 -0.2930 0.3823 0.045 Uiso 1 1 calc R U . . .
C28 C 0.5715(2) -0.19000(17) 0.39511(12) 0.0316(4) Uani 1 1 d . . . . .
H28 H 0.5434 -0.2174 0.4374 0.038 Uiso 1 1 calc R U . . .
C29 C 0.5068(2) -0.10524(16) 0.36466(11) 0.0263(4) Uani 1 1 d . . . . .
C30 C 0.55308(19) -0.06926(16) 0.30132(10) 0.0258(4) Uani 1 1 d . . . . .
B1 B 0.1930(2) 0.20692(16) 0.40155(10) 0.0203(3) Uani 1 1 d . . . . .
B2 B 0.3789(2) 0.04723(18) 0.33831(11) 0.0228(4) Uani 1 1 d . . . . .
N1 N 0.15139(15) 0.14488(11) 0.47095(8) 0.0190(3) Uani 1 1 d . . . . .
N2 N 0.48164(16) 0.01547(14) 0.27940(8) 0.0250(3) Uani 1 1 d . . . . .
O1 O 0.10459(14) 0.30460(10) 0.40773(7) 0.0237(3) Uani 1 1 d . . . . .
O2 O 0.40195(14) -0.04776(11) 0.38552(7) 0.0259(3) Uani 1 1 d . . . . .
Cl1 Cl 0.25160(6) -0.12061(5) 0.22916(3) 0.04231(16) Uani 1 1 d . . . . .
Cl2 Cl 0.32508(5) 0.40478(4) 0.48783(3) 0.03163(12) 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'
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
C6 C1 C2 120.12(17) . .
C6 C1 B1 119.06(16) . .
C2 C1 B1 120.74(15) . .
C3 C2 C1 116.15(17) . .
C3 C2 B2 125.04(17) . .
C1 C2 B2 118.79(16) . .
C4 C3 C2 123.65(19) . .
C4 C3 Cl1 115.60(16) . .
C2 C3 Cl1 120.73(15) . .
C5 C4 C3 118.56(19) . .
C5 C4 H4 120.7 . .
C3 C4 H4 120.7 . .
C4 C5 C6 120.21(19) . .
C4 C5 H5 119.9 . .
C6 C5 H5 119.9 . .
C5 C6 C1 121.02(19) . .
C5 C6 H6 119.5 . .
C1 C6 H6 119.5 . .
C12 C7 C8 119.58(17) . .
C12 C7 B2 118.42(16) . .
C8 C7 B2 121.83(15) . .
C9 C8 C7 116.34(16) . .
C9 C8 B1 126.10(16) . .
C7 C8 B1 117.48(15) . .
C10 C9 C8 124.12(18) . .
C10 C9 Cl2 114.83(15) . .
C8 C9 Cl2 121.04(14) . .
C11 C10 C9 118.45(18) . .
C11 C10 H10 120.8 . .
C9 C10 H10 120.8 . .
C10 C11 C12 119.68(18) . .
C10 C11 H11 120.2 . .
C12 C11 H11 120.2 . .
C11 C12 C7 121.77(18) . .
C11 C12 H12 119.1 . .
C7 C12 H12 119.1 . .
N1 C13 C14 119.70(17) . .
N1 C13 H13 120.1 . .
C14 C13 H13 120.1 . .
C15 C14 C13 120.99(17) . .
C15 C14 H14 119.5 . .
C13 C14 H14 119.5 . .
C14 C15 C16 119.93(16) . .
C14 C15 H15 120.0 . .
C16 C15 H15 120.0 . .
C21 C16 C15 115.33(16) . .
C21 C16 C17 115.70(18) . .
C15 C16 C17 128.97(18) . .
C18 C17 C16 118.99(18) . .
C18 C17 H17 120.5 . .
C16 C17 H17 120.5 . .
C17 C18 C19 124.61(18) . .
C17 C18 H18 117.7 . .
C19 C18 H18 117.7 . .
C20 C19 C18 117.26(19) . .
C20 C19 H19 121.4 . .
C18 C19 H19 121.4 . .
O1 C20 C19 129.28(18) . .
O1 C20 C21 112.42(15) . .
C19 C20 C21 118.29(17) . .
N1 C21 C16 124.10(17) . .
N1 C21 C20 110.75(15) . .
C16 C21 C20 125.15(16) . .
N2 C22 C23 119.5(2) . .
N2 C22 H22 120.3 . .
C23 C22 H22 120.3 . .
C24 C23 C22 121.2(2) . .
C24 C23 H23 119.4 . .
C22 C23 H23 119.4 . .
C23 C24 C25 120.14(19) . .
C23 C24 H24 119.9 . .
C25 C24 H24 119.9 . .
C30 C25 C26 115.9(2) . .
C30 C25 C24 114.8(2) . .
C26 C25 C24 129.2(2) . .
C27 C26 C25 119.3(2) . .
C27 C26 H26 120.3 . .
C25 C26 H26 120.3 . .
C26 C27 C28 124.0(2) . .
C26 C27 H27 118.0 . .
C28 C27 H27 118.0 . .
C29 C28 C27 117.6(2) . .
C29 C28 H28 121.2 . .
C27 C28 H28 121.2 . .
O2 C29 C28 130.0(2) . .
O2 C29 C30 111.84(17) . .
C28 C29 C30 118.16(19) . .
N2 C30 C25 124.4(2) . .
N2 C30 C29 110.71(16) . .
C25 C30 C29 124.9(2) . .
O1 B1 C1 109.60(15) . .
O1 B1 C8 115.62(15) . .
C1 B1 C8 114.57(14) . .
O1 B1 N1 99.11(13) . .
C1 B1 N1 108.80(14) . .
C8 B1 N1 107.81(14) . .
O2 B2 C2 113.05(15) . .
O2 B2 N2 98.96(14) . .
C2 B2 N2 112.63(15) . .
O2 B2 C7 109.64(15) . .
C2 B2 C7 114.58(16) . .
N2 B2 C7 106.73(14) . .
C13 N1 C21 119.94(15) . .
C13 N1 B1 132.93(15) . .
C21 N1 B1 107.13(14) . .
C22 N2 C30 119.96(17) . .
C22 N2 B2 132.12(18) . .
C30 N2 B2 107.75(16) . .
C20 O1 B1 110.57(14) . .
C29 O2 B2 109.88(15) . .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
C1 C6 1.406(3) .
C1 C2 1.418(3) .
C1 B1 1.604(3) .
C2 C3 1.406(3) .
C2 B2 1.604(3) .
C3 C4 1.393(3) .
C3 Cl1 1.760(2) .
C4 C5 1.380(3) .
C4 H4 0.9500 .
C5 C6 1.388(3) .
C5 H5 0.9500 .
C6 H6 0.9500 .
C7 C12 1.410(3) .
C7 C8 1.416(3) .
C7 B2 1.619(3) .
C8 C9 1.396(3) .
C8 B1 1.618(3) .
C9 C10 1.395(3) .
C9 Cl2 1.7618(19) .
C10 C11 1.382(3) .
C10 H10 0.9500 .
C11 C12 1.383(3) .
C11 H11 0.9500 .
C12 H12 0.9500 .
C13 N1 1.330(2) .
C13 C14 1.408(2) .
C13 H13 0.9500 .
C14 C15 1.375(3) .
C14 H14 0.9500 .
C15 C16 1.416(3) .
C15 H15 0.9500 .
C16 C21 1.404(2) .
C16 C17 1.421(3) .
C17 C18 1.375(3) .
C17 H17 0.9500 .
C18 C19 1.419(3) .
C18 H18 0.9500 .
C19 C20 1.380(3) .
C19 H19 0.9500 .
C20 O1 1.339(2) .
C20 C21 1.407(3) .
C21 N1 1.356(2) .
C22 N2 1.327(3) .
C22 C23 1.408(3) .
C22 H22 0.9500 .
C23 C24 1.358(4) .
C23 H23 0.9500 .
C24 C25 1.419(3) .
C24 H24 0.9500 .
C25 C30 1.404(3) .
C25 C26 1.411(3) .
C26 C27 1.377(4) .
C26 H26 0.9500 .
C27 C28 1.425(3) .
C27 H27 0.9500 .
C28 C29 1.373(3) .
C28 H28 0.9500 .
C29 O2 1.341(2) .
C29 C30 1.414(3) .
C30 N2 1.344(3) .
B1 O1 1.516(2) .
B1 N1 1.634(2) .
B2 O2 1.525(3) .
B2 N2 1.616(2) .
