#------------------------------------------------------------------------------
#$Date: 2016-02-18 17:37:37 +0200 (Thu, 18 Feb 2016) $
#$Revision: 176729 $
#$URL: svn://www.crystallography.net/cod/cif/1/51/66/1516658.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_1516658
loop_
_publ_author_name
'Leung, Man-kit'
'Yang, Chih-Chiang'
'Lee, Jiun-Haw'
'Tsai, Hsin-Hung'
'Lin, Chi-Feng'
'Huang, Chih-Yen'
'Su, Yuhlong Oliver'
'Chiu, Chi-Feng'
_publ_section_title
;
 The unusual electrochemical and photophysical behavior of
 2,2'-bis(1,3,4-oxadiazol-2-yl)biphenyls, effective electron transport
 hosts for phosphorescent organic light emitting diodes.
;
_journal_issue                   2
_journal_name_full               'Organic letters'
_journal_page_first              235
_journal_page_last               238
_journal_paper_doi               10.1021/ol062668+
_journal_volume                  9
_journal_year                    2007
_chemical_formula_sum            'C53 H33 Cl3 N6 O2'
_chemical_formula_weight         892.20
_chemical_name_systematic
; 
 ? 
;
_space_group_IT_number           13
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2yc'
_symmetry_space_group_name_H-M   'P 1 2/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                 102.3840(10)
_cell_angle_gamma                90.00
_cell_formula_units_Z            2
_cell_length_a                   11.0052(2)
_cell_length_b                   13.4251(2)
_cell_length_c                   14.8416(3)
_cell_measurement_reflns_used    31830
_cell_measurement_temperature    295(2)
_cell_measurement_theta_max      27.5
_cell_measurement_theta_min      1
_cell_volume                     2141.76(7)
_computing_cell_refinement       'HKL Denzo & Scalepack (Otwinowski & Minor)'
_computing_data_collection       'COLLECT (Nonius BV)'
_computing_data_reduction        'HKL Denzo & Scalepack (Otwinowski & Minor)'
_computing_molecular_graphics    SHELXTL
_computing_publication_material  SHELXTL
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      295(2)
_diffrn_measured_fraction_theta_full 0.984
_diffrn_measured_fraction_theta_max 0.984
_diffrn_measurement_device_type  'Nonius KappaCCD'
_diffrn_measurement_method       CCD
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0495
_diffrn_reflns_av_sigmaI/netI    0.0399
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            15147
_diffrn_reflns_theta_full        27.47
_diffrn_reflns_theta_max         27.47
_diffrn_reflns_theta_min         1.89
_exptl_absorpt_coefficient_mu    0.266
_exptl_absorpt_correction_T_max  0.988
_exptl_absorpt_correction_T_min  0.961
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
; 
multi-scan from symmetry-related measurements 
 Sortav (Blessing 1995) 
;
_exptl_crystal_density_diffrn    1.383
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             920
_exptl_crystal_size_max          0.30
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.15
_refine_diff_density_max         0.689
_refine_diff_density_min         -0.563
_refine_diff_density_rms         0.087
_refine_ls_extinction_coef       0.16(2)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     SHELXL
_refine_ls_goodness_of_fit_ref   1.722
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     300
_refine_ls_number_reflns         4846
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.722
_refine_ls_R_factor_all          0.1070
_refine_ls_R_factor_gt           0.0780
_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)+(0.1000P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2245
_refine_ls_wR_factor_ref         0.2490
_reflns_number_gt                3407
_reflns_number_total             4846
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ol062668%2Bsi20061101_081023.cif
_cod_data_source_block           ic12132
_cod_depositor_comments
;
The following automatic conversions were performed:

'_symmetry_cell_setting' value 'Monoclinic' changed to 'monoclinic'
according to
/usr/data/users/saulius/automatic-downloads/retrospective/ACS/lib/dictionaries/cif_core.dic
dictionary named 'cif_core.dic' version 2.4.2 from 2011-04-26.

Automatic conversion script
Id: cif_fix_values 2281 2013-09-26 08:29:07Z andrius 
;
_cod_original_sg_symbol_H-M      P2/c
_cod_database_code               1516658
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y, -z+1/2'
'-x, -y, -z'
'x, -y, 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
O1 O 0.12262(13) 0.23552(10) 0.84863(9) 0.0486(4) Uani 1 1 d .
N1 N 0.26475(18) 0.03731(15) 0.51815(12) 0.0583(5) Uani 1 1 d .
N2 N 0.1821(2) 0.31610(15) 0.73643(14) 0.0709(6) Uani 1 1 d .
N3 N 0.1841(2) 0.38204(14) 0.80920(14) 0.0727(6) Uani 1 1 d .
C1 C 0.3196(2) -0.05118(18) 0.49691(15) 0.0557(6) Uani 1 1 d .
C2 C 0.3395(2) -0.13989(19) 0.54575(18) 0.0652(7) Uani 1 1 d .
H2A H 0.3116 -0.1483 0.6001 0.078 Uiso 1 1 calc R
C3 C 0.4018(2) -0.2152(2) 0.5116(2) 0.0759(8) Uani 1 1 d .
H3A H 0.4162 -0.2753 0.5433 0.091 Uiso 1 1 calc R
C4 C 0.4434(3) -0.2022(3) 0.4301(2) 0.0861(9) Uani 1 1 d .
H4A H 0.4847 -0.2541 0.4078 0.103 Uiso 1 1 calc R
C5 C 0.4247(2) -0.1152(3) 0.38270(19) 0.0777(8) Uani 1 1 d .
H5A H 0.4533 -0.1076 0.3285 0.093 Uiso 1 1 calc R
C6 C 0.3622(2) -0.0369(2) 0.41551(16) 0.0648(7) Uani 1 1 d .
C7 C 0.3303(2) 0.0628(2) 0.38482(15) 0.0653(7) Uani 1 1 d .
C8 C 0.3455(3) 0.1165(3) 0.30808(18) 0.0815(9) Uani 1 1 d .
H8A H 0.3841 0.0877 0.2645 0.098 Uiso 1 1 calc R
C9 C 0.3032(3) 0.2116(3) 0.2976(2) 0.0947(10) Uani 1 1 d .
H9A H 0.3134 0.2480 0.2465 0.114 Uiso 1 1 calc R
C10 C 0.2451(3) 0.2558(3) 0.3618(2) 0.0895(9) Uani 1 1 d .
H10A H 0.2172 0.3211 0.3528 0.107 Uiso 1 1 calc R
C11 C 0.2280(3) 0.2043(2) 0.43863(18) 0.0726(7) Uani 1 1 d .
H11A H 0.1888 0.2337 0.4815 0.087 Uiso 1 1 calc R
C12 C 0.2712(2) 0.10727(18) 0.44945(15) 0.0588(6) Uani 1 1 d .
C13 C 0.1918(2) 0.04710(16) 0.58565(14) 0.0509(5) Uani 1 1 d .
C14 C 0.1057(2) -0.02632(16) 0.59391(15) 0.0536(6) Uani 1 1 d .
H14A H 0.0967 -0.0817 0.5554 0.064 Uiso 1 1 calc R
C15 C 0.0336(2) -0.01754(15) 0.65877(15) 0.0505(5) Uani 1 1 d .
H15A H -0.0218 -0.0683 0.6644 0.061 Uiso 1 1 calc R
C16 C 0.04174(18) 0.06557(15) 0.71636(13) 0.0446(5) Uani 1 1 d .
C17 C 0.12866(18) 0.13914(15) 0.70811(13) 0.0457(5) Uani 1 1 d .
C18 C 0.20402(19) 0.12879(16) 0.64383(14) 0.0510(5) Uani 1 1 d .
H18A H 0.2630 0.1774 0.6401 0.061 Uiso 1 1 calc R
C19 C 0.14613(19) 0.23117(15) 0.76241(14) 0.0476(5) Uani 1 1 d .
C20 C 0.1484(2) 0.33260(15) 0.87323(15) 0.0528(5) Uani 1 1 d .
C21 C 0.1345(2) 0.36717(16) 0.96306(16) 0.0574(6) Uani 1 1 d .
C22 C 0.0796(3) 0.3073(2) 1.01937(17) 0.0688(7) Uani 1 1 d .
H22A H 0.0498 0.2446 0.9990 0.083 Uiso 1 1 calc R
C23 C 0.0690(3) 0.3403(2) 1.10555(19) 0.0824(8) Uani 1 1 d .
H23A H 0.0332 0.2997 1.1434 0.099 Uiso 1 1 calc R
C24 C 0.1121(3) 0.4344(3) 1.1353(2) 0.0881(9) Uani 1 1 d .
H24A H 0.1053 0.4570 1.1932 0.106 Uiso 1 1 calc R
C25 C 0.1642(3) 0.4933(2) 1.0796(2) 0.0882(9) Uani 1 1 d .
H25A H 0.1919 0.5566 1.0995 0.106 Uiso 1 1 calc R
C26 C 0.1769(3) 0.46096(19) 0.99383(19) 0.0749(8) Uani 1 1 d .
H26A H 0.2138 0.5020 0.9568 0.090 Uiso 1 1 calc R
Cl1 Cl 0.5000 0.62334(16) 0.2500 0.2102(14) Uani 1 2 d S
Cl2 Cl 0.5000 0.4131(2) 0.2500 0.319(3) Uani 1 2 d S
Cl3 Cl 0.5162(3) 0.4945(3) 0.1091(3) 0.1990(17) Uani 0.50 1 d P
C27 C 0.5471(8) 0.5175(7) 0.2183(7) 0.131(3) Uani 0.50 1 d P
H27A H 0.6360 0.5174 0.2385 0.157 Uiso 0.50 1 d PR
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'
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
C19 O1 C20 102.82(16) . .
C1 N1 C12 108.30(18) . .
C1 N1 C13 125.09(19) . .
C12 N1 C13 125.3(2) . .
C19 N2 N3 106.51(18) . .
C20 N3 N2 106.74(18) . .
C2 C1 N1 129.7(2) . .
C2 C1 C6 121.6(2) . .
N1 C1 C6 108.6(2) . .
C3 C2 C1 118.3(2) . .
C3 C2 H2A 120.9 . .
C1 C2 H2A 120.9 . .
C2 C3 C4 120.7(3) . .
C2 C3 H3A 119.7 . .
C4 C3 H3A 119.7 . .
C5 C4 C3 121.1(3) . .
C5 C4 H4A 119.5 . .
C3 C4 H4A 119.5 . .
C4 C5 C6 119.8(3) . .
C4 C5 H5A 120.1 . .
C6 C5 H5A 120.1 . .
C5 C6 C1 118.6(3) . .
C5 C6 C7 134.1(2) . .
C1 C6 C7 107.3(2) . .
C8 C7 C12 119.7(3) . .
C8 C7 C6 132.9(3) . .
C12 C7 C6 107.4(2) . .
C9 C8 C7 118.9(3) . .
C9 C8 H8A 120.5 . .
C7 C8 H8A 120.5 . .
C8 C9 C10 121.4(3) . .
C8 C9 H9A 119.3 . .
C10 C9 H9A 119.3 . .
C11 C10 C9 121.1(3) . .
C11 C10 H10A 119.4 . .
C9 C10 H10A 119.4 . .
C10 C11 C12 117.5(3) . .
C10 C11 H11A 121.2 . .
C12 C11 H11A 121.2 . .
C11 C12 N1 130.2(2) . .
C11 C12 C7 121.3(2) . .
N1 C12 C7 108.4(2) . .
C18 C13 C14 118.89(19) . .
C18 C13 N1 121.37(19) . .
C14 C13 N1 119.75(19) . .
C15 C14 C13 120.4(2) . .
C15 C14 H14A 119.8 . .
C13 C14 H14A 119.8 . .
C14 C15 C16 121.69(19) . .
C14 C15 H15A 119.2 . .
C16 C15 H15A 119.2 . .
C15 C16 C17 117.76(18) . .
C15 C16 C16 116.17(14) . 2_556
C17 C16 C16 126.04(15) . 2_556
C16 C17 C18 120.42(18) . .
C16 C17 C19 123.98(18) . .
C18 C17 C19 115.58(18) . .
C13 C18 C17 120.78(19) . .
C13 C18 H18A 119.6 . .
C17 C18 H18A 119.6 . .
N2 C19 O1 112.03(18) . .
N2 C19 C17 126.31(19) . .
O1 C19 C17 121.65(17) . .
N3 C20 O1 111.90(19) . .
N3 C20 C21 128.5(2) . .
O1 C20 C21 119.60(19) . .
C26 C21 C22 119.1(2) . .
C26 C21 C20 120.0(2) . .
C22 C21 C20 120.9(2) . .
C23 C22 C21 120.4(3) . .
C23 C22 H22A 119.8 . .
C21 C22 H22A 119.8 . .
C22 C23 C24 119.7(3) . .
C22 C23 H23A 120.1 . .
C24 C23 H23A 120.1 . .
C25 C24 C23 119.8(3) . .
C25 C24 H24A 120.1 . .
C23 C24 H24A 120.1 . .
C24 C25 C26 121.2(3) . .
C24 C25 H25A 119.4 . .
C26 C25 H25A 119.4 . .
C25 C26 C21 119.8(3) . .
C25 C26 H26A 120.1 . .
C21 C26 H26A 120.1 . .
C27 Cl1 C27 57.0(6) . 2_655
C27 Cl2 C27 57.6(7) 2_655 .
C27 Cl2 Cl3 41.9(4) 2_655 2_655
C27 Cl2 Cl3 86.9(4) . 2_655
C27 Cl2 Cl3 86.9(4) 2_655 .
C27 Cl2 Cl3 41.9(4) . .
Cl3 Cl2 Cl3 125.81(18) 2_655 .
C27 Cl3 Cl2 41.5(4) . .
C27 C27 Cl2 61.2(3) 2_655 .
C27 C27 Cl3 126.0(9) 2_655 .
Cl2 C27 Cl3 96.7(6) . .
C27 C27 Cl1 61.5(3) 2_655 .
Cl2 C27 Cl1 122.7(5) . .
Cl3 C27 Cl1 116.7(6) . .
C27 C27 H27A 125.7 2_655 .
Cl2 C27 H27A 106.3 . .
Cl3 C27 H27A 107.1 . .
Cl1 C27 H27A 106.2 . .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
O1 C19 1.360(2) .
O1 C20 1.367(2) .
N1 C1 1.399(3) .
N1 C12 1.399(3) .
N1 C13 1.417(3) .
N2 C19 1.293(3) .
N2 N3 1.393(3) .
N3 C20 1.288(3) .
C1 C2 1.387(4) .
C1 C6 1.400(3) .
C2 C3 1.377(4) .
C2 H2A 0.9300 .
C3 C4 1.394(4) .
C3 H3A 0.9300 .
C4 C5 1.356(5) .
C4 H4A 0.9300 .
C5 C6 1.399(4) .
C5 H5A 0.9300 .
C6 C7 1.433(4) .
C7 C8 1.388(4) .
C7 C12 1.402(3) .
C8 C9 1.357(5) .
C8 H8A 0.9300 .
C9 C10 1.388(5) .
C9 H9A 0.9300 .
C10 C11 1.381(4) .
C10 H10A 0.9300 .
C11 C12 1.384(4) .
C11 H11A 0.9300 .
C13 C18 1.384(3) .
C13 C14 1.391(3) .
C14 C15 1.378(3) .
C14 H14A 0.9300 .
C15 C16 1.397(3) .
C15 H15A 0.9300 .
C16 C17 1.398(3) .
C16 C16 1.495(4) 2_556
C17 C18 1.399(3) .
C17 C19 1.465(3) .
C18 H18A 0.9300 .
C20 C21 1.450(3) .
C21 C26 1.386(3) .
C21 C22 1.388(4) .
C22 C23 1.382(4) .
C22 H22A 0.9300 .
C23 C24 1.387(4) .
C23 H23A 0.9300 .
C24 C25 1.358(5) .
C24 H24A 0.9300 .
C25 C26 1.380(4) .
C25 H25A 0.9300 .
C26 H26A 0.9300 .
Cl1 C27 1.617(10) .
Cl1 C27 1.617(10) 2_655
Cl2 C27 1.600(9) 2_655
Cl2 C27 1.600(9) .
Cl2 Cl3 2.400(5) 2_655
Cl2 Cl3 2.400(5) .
Cl3 C27 1.613(10) .
C27 C27 1.542(17) 2_655
C27 H27A 0.9599 .
