#------------------------------------------------------------------------------
#$Date: 2016-02-14 06:40:26 +0200 (Sun, 14 Feb 2016) $
#$Revision: 176432 $
#$URL: svn://www.crystallography.net/cod/cif/4/33/61/4336141.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_4336141
loop_
_publ_author_name
'Grzegorz Wesela-Bauman'
'Paulina Ciećwierz'
'Krzysztof Durka'
'Sergiusz Luliński'
'Janusz Serwatowski'
'Krzysztof Woźniak'
_publ_section_title
;
 Heteroleptic (2-Fluoro-3-pyridyl)arylborinic 8-Oxyquinolinates for the
 Potential Application in Organic Light-Emitting Devices
;
_journal_name_full               'Inorganic Chemistry'
_journal_page_first              10846
_journal_page_last               10859
_journal_paper_doi               10.1021/ic400729t
_journal_volume                  52
_journal_year                    2013
_chemical_formula_moiety         '2(C40 H28 B2 Cl2 F2 N4 O2 Zn), H2 O'
_chemical_formula_sum            'C80 H58 B4 Cl4 F4 N8 O5 Zn2'
_chemical_formula_weight         1603.16
_chemical_name_systematic
; 
 ? 
;
_space_group_IT_number           60
_symmetry_cell_setting           orthorhombic
_symmetry_Int_Tables_number      60
_symmetry_space_group_name_Hall  '-P 2n 2ab'
_symmetry_space_group_name_H-M   'P b c n'
_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                 90.00
_cell_angle_gamma                90.00
_cell_formula_units_Z            2
_cell_length_a                   14.2809(3)
_cell_length_b                   8.1483(2)
_cell_length_c                   31.1999(7)
_cell_measurement_temperature    100(1)
_cell_measurement_theta_max      32.4945
_cell_measurement_theta_min      1.9296
_cell_volume                     3630.58(14)
_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 0.978
_diffrn_measured_fraction_theta_max 0.978
_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  0.0827
_diffrn_reflns_av_sigmaI/netI    0.0425
_diffrn_reflns_limit_h_max       20
_diffrn_reflns_limit_h_min       -21
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       46
_diffrn_reflns_limit_l_min       -47
_diffrn_reflns_number            93231
_diffrn_reflns_theta_full        32.56
_diffrn_reflns_theta_max         32.56
_diffrn_reflns_theta_min         2.61
_diffrn_source                   'rotating-anode x-ray source'
_exptl_absorpt_coefficient_mu    0.878
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.90748
_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    1.466
_exptl_crystal_description       unspecific
_exptl_crystal_F_000             1636
_exptl_crystal_size_max          0.12
_exptl_crystal_size_mid          0.08
_exptl_crystal_size_min          0.02
_refine_diff_density_max         0.484
_refine_diff_density_min         -0.370
_refine_diff_density_rms         0.081
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.102
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     245
_refine_ls_number_reflns         6456
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.102
_refine_ls_R_factor_all          0.0788
_refine_ls_R_factor_gt           0.0473
_refine_ls_shift/su_max          0.002
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0475P)²+0.9705P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0919
_refine_ls_wR_factor_ref         0.1021
_reflns_number_gt                4835
_reflns_number_total             6456
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ic400729t_si_002_1.cif
_cod_data_source_block           17
_cod_original_sg_symbol_Hall     -P2n2ab
_cod_database_code               4336141
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x+1/2, -y+1/2, z+1/2'
'-x, y, -z+1/2'
'x+1/2, -y+1/2, -z'
'-x, -y, -z'
'x-1/2, y-1/2, -z-1/2'
'x, -y, z-1/2'
'-x-1/2, y-1/2, 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
O2 O 0.5000 0.6872(6) 0.2500 0.0512(14) Uani 0.50 2 d SP
H2A H 0.5415 0.6218 0.2585 0.077 Uiso 0.50 1 calc PR
Cl1 Cl 0.38258(3) 1.34912(5) 0.226135(14) 0.02163(10) Uani 1 1 d .
C1 C 0.34744(13) 0.6626(2) 0.14771(6) 0.0204(3) Uani 1 1 d .
H1 H 0.3792 0.6026 0.1694 0.024 Uiso 1 1 calc R
C2 C 0.24900(13) 0.6663(2) 0.14684(6) 0.0244(4) Uani 1 1 d .
H2 H 0.2147 0.6103 0.1684 0.029 Uiso 1 1 calc R
C3 C 0.20168(12) 0.7496(2) 0.11531(7) 0.0255(4) Uani 1 1 d .
H3 H 0.1352 0.7508 0.1152 0.031 Uiso 1 1 calc R
C4 C 0.25220(12) 0.8338(2) 0.08296(6) 0.0210(3) Uani 1 1 d .
C5 C 0.21798(13) 0.9249(2) 0.04758(6) 0.0266(4) Uani 1 1 d .
H5 H 0.1525 0.9341 0.0428 0.032 Uiso 1 1 calc R
C6 C 0.27996(14) 0.9994(2) 0.02036(6) 0.0257(4) Uani 1 1 d .
H6 H 0.2554 1.0592 -0.0033 0.031 Uiso 1 1 calc R
C7 C 0.37866(13) 0.9928(2) 0.02530(6) 0.0212(3) Uani 1 1 d .
H7 H 0.4191 1.0483 0.0060 0.025 Uiso 1 1 calc R
C8 C 0.41375(11) 0.9032(2) 0.05907(5) 0.0161(3) Uani 1 1 d .
C9 C 0.34983(11) 0.82590(19) 0.08693(5) 0.0152(3) Uani 1 1 d .
C10 C 0.54542(11) 0.5797(2) 0.09669(5) 0.0146(3) Uani 1 1 d .
C11 C 0.55825(12) 0.5311(2) 0.05414(5) 0.0181(3) Uani 1 1 d .
H11 H 0.5489 0.6087 0.0318 0.022 Uiso 1 1 calc R
C12 C 0.58442(13) 0.3713(2) 0.04367(6) 0.0217(4) Uani 1 1 d .
H12 H 0.5920 0.3411 0.0145 0.026 Uiso 1 1 calc R
C13 C 0.59939(13) 0.2562(2) 0.07559(6) 0.0223(4) Uani 1 1 d .
H13 H 0.6168 0.1471 0.0685 0.027 Uiso 1 1 calc R
C14 C 0.58860(14) 0.3026(2) 0.11810(6) 0.0235(4) Uani 1 1 d .
H14 H 0.5997 0.2252 0.1403 0.028 Uiso 1 1 calc R
C15 C 0.56157(12) 0.4619(2) 0.12841(6) 0.0198(3) Uani 1 1 d .
H15 H 0.5539 0.4912 0.1577 0.024 Uiso 1 1 calc R
C17 C 0.56271(11) 0.84558(19) 0.14812(5) 0.0143(3) Uani 1 1 d .
C18 C 0.52448(11) 0.95172(19) 0.17813(5) 0.0141(3) Uani 1 1 d .
C19 C 0.66089(11) 1.0028(2) 0.21370(6) 0.0194(3) Uani 1 1 d .
H20 H 0.6943 1.0558 0.2361 0.023 Uiso 1 1 calc R
C20 C 0.70832(12) 0.9003(2) 0.18625(6) 0.0251(4) Uani 1 1 d .
H19 H 0.7737 0.8826 0.1896 0.030 Uiso 1 1 calc R
C21 C 0.65905(12) 0.8228(2) 0.15349(6) 0.0212(3) Uani 1 1 d .
H18 H 0.6917 0.7527 0.1343 0.025 Uiso 1 1 calc R
B1 B 0.50656(12) 0.7599(2) 0.10860(6) 0.0147(3) Uani 1 1 d .
N1 N 0.39579(9) 0.74291(17) 0.11815(4) 0.0150(3) Uani 1 1 d .
N2 N 0.56810(9) 1.03019(17) 0.20962(4) 0.0143(3) Uani 1 1 d .
O1 O 0.50318(8) 0.87399(15) 0.07033(4) 0.0163(2) Uani 1 1 d .
Zn1 Zn 0.5000 1.19365(3) 0.2500 0.01439(7) Uani 1 2 d S
F1 F 0.43252(7) 0.98667(14) 0.17674(4) 0.0264(2) 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'
Zn Zn 0.2839 1.4301 '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'
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
N1 C1 C2 119.77(17) . .
N1 C1 H1 120.1 . .
C2 C1 H1 120.1 . .
C3 C2 C1 121.11(17) . .
C3 C2 H2 119.4 . .
C1 C2 H2 119.4 . .
C2 C3 C4 119.92(16) . .
C2 C3 H3 120.0 . .
C4 C3 H3 120.0 . .
C9 C4 C5 115.85(17) . .
C9 C4 C3 114.92(16) . .
C5 C4 C3 129.23(17) . .
C6 C5 C4 119.52(17) . .
C6 C5 H5 120.2 . .
C4 C5 H5 120.2 . .
C5 C6 C7 123.92(18) . .
C5 C6 H6 118.0 . .
C7 C6 H6 118.0 . .
C8 C7 C6 117.71(17) . .
C8 C7 H7 121.1 . .
C6 C7 H7 121.1 . .
O1 C8 C7 129.73(16) . .
O1 C8 C9 112.00(14) . .
C7 C8 C9 118.27(15) . .
N1 C9 C4 124.63(16) . .
N1 C9 C8 110.66(14) . .
C4 C9 C8 124.71(16) . .
C11 C10 C15 117.14(15) . .
C11 C10 B1 121.47(14) . .
C15 C10 B1 121.24(14) . .
C12 C11 C10 121.51(16) . .
C12 C11 H11 119.2 . .
C10 C11 H11 119.2 . .
C13 C12 C11 120.37(16) . .
C13 C12 H12 119.8 . .
C11 C12 H12 119.8 . .
C12 C13 C14 119.09(16) . .
C12 C13 H13 120.5 . .
C14 C13 H13 120.5 . .
C13 C14 C15 120.37(17) . .
C13 C14 H14 119.8 . .
C15 C14 H14 119.8 . .
C14 C15 C10 121.50(16) . .
C14 C15 H15 119.3 . .
C10 C15 H15 119.3 . .
C18 C17 C21 112.90(14) . .
C18 C17 B1 125.79(14) . .
C21 C17 B1 121.24(14) . .
N2 C18 F1 112.35(13) . .
N2 C18 C17 127.98(15) . .
F1 C18 C17 119.66(14) . .
N2 C19 C20 121.68(15) . .
N2 C19 H20 119.2 . .
C20 C19 H20 119.2 . .
C19 C20 C21 118.93(16) . .
C19 C20 H19 120.5 . .
C21 C20 H19 120.5 . .
C20 C21 C17 121.68(16) . .
C20 C21 H18 119.2 . .
C17 C21 H18 119.2 . .
O1 B1 C10 112.83(13) . .
O1 B1 N1 99.61(12) . .
C10 B1 N1 107.52(13) . .
O1 B1 C17 110.48(13) . .
C10 B1 C17 113.28(13) . .
N1 B1 C17 112.30(13) . .
C1 N1 C9 119.63(15) . .
C1 N1 B1 132.91(15) . .
C9 N1 B1 107.38(13) . .
C18 N2 C19 116.81(14) . .
C18 N2 Zn1 122.58(11) . .
C19 N2 Zn1 120.58(11) . .
C8 O1 B1 110.16(12) . .
N2 Zn1 N2 100.16(7) 3_655 .
N2 Zn1 Cl1 120.95(4) 3_655 3_655
N2 Zn1 Cl1 102.41(4) . 3_655
N2 Zn1 Cl1 102.41(4) 3_655 .
N2 Zn1 Cl1 120.95(4) . .
Cl1 Zn1 Cl1 110.75(3) 3_655 .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
O2 H2A 0.8400 .
Cl1 Zn1 2.2296(4) .
C1 N1 1.325(2) .
C1 C2 1.406(3) .
C1 H1 0.9500 .
C2 C3 1.373(3) .
C2 H2 0.9500 .
C3 C4 1.417(3) .
C3 H3 0.9500 .
C4 C9 1.401(2) .
C4 C5 1.417(3) .
C5 C6 1.369(3) .
C5 H5 0.9500 .
C6 C7 1.419(3) .
C6 H6 0.9500 .
C7 C8 1.376(2) .
C7 H7 0.9500 .
C8 O1 1.3458(19) .
C8 C9 1.409(2) .
C9 N1 1.355(2) .
C10 C11 1.397(2) .
C10 C15 1.398(2) .
C10 B1 1.613(2) .
C11 C12 1.394(2) .
C11 H11 0.9500 .
C12 C13 1.384(3) .
C12 H12 0.9500 .
C13 C14 1.388(3) .
C13 H13 0.9500 .
C14 C15 1.392(2) .
C14 H14 0.9500 .
C15 H15 0.9500 .
C17 C18 1.387(2) .
C17 C21 1.398(2) .
C17 B1 1.628(2) .
C18 N2 1.327(2) .
C18 F1 1.3445(18) .
C19 N2 1.350(2) .
C19 C20 1.375(2) .
C19 H20 0.9500 .
C20 C21 1.392(2) .
C20 H19 0.9500 .
C21 H18 0.9500 .
B1 O1 1.514(2) .
B1 N1 1.616(2) .
N2 Zn1 2.0754(14) .
Zn1 N2 2.0754(14) 3_655
Zn1 Cl1 2.2296(4) 3_655
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_4
N1 C1 C2 C3 1.2(3) .
C1 C2 C3 C4 -0.1(3) .
C2 C3 C4 C9 -1.2(2) .
C2 C3 C4 C5 179.27(17) .
C9 C4 C5 C6 -0.7(2) .
C3 C4 C5 C6 178.86(18) .
C4 C5 C6 C7 -0.5(3) .
C5 C6 C7 C8 1.3(3) .
C6 C7 C8 O1 178.24(16) .
C6 C7 C8 C9 -0.9(2) .
C5 C4 C9 N1 -178.96(15) .
C3 C4 C9 N1 1.4(2) .
C5 C4 C9 C8 1.1(2) .
C3 C4 C9 C8 -178.54(15) .
O1 C8 C9 N1 0.48(19) .
C7 C8 C9 N1 179.80(14) .
O1 C8 C9 C4 -179.57(14) .
C7 C8 C9 C4 -0.3(2) .
C15 C10 C11 C12 1.1(2) .
B1 C10 C11 C12 -174.65(15) .
C10 C11 C12 C13 -0.7(3) .
C11 C12 C13 C14 -0.4(3) .
C12 C13 C14 C15 1.1(3) .
C13 C14 C15 C10 -0.6(3) .
C11 C10 C15 C14 -0.5(3) .
B1 C10 C15 C14 175.30(16) .
C21 C17 C18 N2 0.4(2) .
B1 C17 C18 N2 -176.65(15) .
C21 C17 C18 F1 179.41(14) .
B1 C17 C18 F1 2.4(2) .
N2 C19 C20 C21 -0.1(3) .
C19 C20 C21 C17 -0.6(3) .
C18 C17 C21 C20 0.5(2) .
B1 C17 C21 C20 177.62(17) .
C11 C10 B1 O1 -10.2(2) .
C15 C10 B1 O1 174.22(14) .
C11 C10 B1 N1 98.63(17) .
C15 C10 B1 N1 -76.94(18) .
C11 C10 B1 C17 -136.68(16) .
C15 C10 B1 C17 47.7(2) .
C18 C17 B1 O1 84.91(19) .
C21 C17 B1 O1 -91.85(18) .
C18 C17 B1 C10 -147.38(16) .
C21 C17 B1 C10 35.9(2) .
C18 C17 B1 N1 -25.3(2) .
C21 C17 B1 N1 157.92(15) .
C2 C1 N1 C9 -1.0(2) .
C2 C1 N1 B1 -177.56(16) .
C4 C9 N1 C1 -0.3(2) .
C8 C9 N1 C1 179.64(14) .
C4 C9 N1 B1 177.03(15) .
C8 C9 N1 B1 -3.03(17) .
O1 B1 N1 C1 -179.04(16) .
C10 B1 N1 C1 63.2(2) .
C17 B1 N1 C1 -62.1(2) .
O1 B1 N1 C9 4.12(15) .
C10 B1 N1 C9 -113.66(14) .
C17 B1 N1 C9 121.06(14) .
F1 C18 N2 C19 179.90(14) .
C17 C18 N2 C19 -1.0(2) .
F1 C18 N2 Zn1 -2.02(19) .
C17 C18 N2 Zn1 177.09(13) .
C20 C19 N2 C18 0.8(3) .
C20 C19 N2 Zn1 -177.31(14) .
C7 C8 O1 B1 -176.70(17) .
C9 C8 O1 B1 2.51(18) .
C10 B1 O1 C8 109.84(15) .
N1 B1 O1 C8 -3.90(16) .
C17 B1 O1 C8 -122.20(14) .
C18 N2 Zn1 N2 77.84(12) 3_655
C19 N2 Zn1 N2 -104.15(13) 3_655
C18 N2 Zn1 Cl1 -157.10(12) 3_655
C19 N2 Zn1 Cl1 20.91(13) 3_655
C18 N2 Zn1 Cl1 -33.39(14) .
C19 N2 Zn1 Cl1 144.62(12) .
