#------------------------------------------------------------------------------
#$Date: 2016-02-18 17:37:37 +0200 (Thu, 18 Feb 2016) $
#$Revision: 176729 $
#$URL: svn://www.crystallography.net/cod/cif/1/51/79/1517974.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_1517974
loop_
_publ_author_name
'Huang, Jau-Jiun'
'Leung, Man-Kit'
'Chiu, Tien-Lung'
'Chuang, Ya-Ting'
'Chou, Pi-Tai'
'Hung, Yu-Hsiang'
_publ_section_title
;
 Novel Benzimidazole Derivatives as Electron-Transporting Type Host To
 Achieve Highly Efficient Sky-Blue Phosphorescent Organic Light-Emitting
 Diode (PHOLED) Device.
;
_journal_issue                   20
_journal_name_full               'Organic letters'
_journal_page_first              5398
_journal_page_last               5401
_journal_paper_doi               10.1021/ol502602t
_journal_volume                  16
_journal_year                    2014
_chemical_formula_sum            'C40 H30 Cl4 N4'
_chemical_formula_weight         708.48
_chemical_name_systematic
; 
 ? 
;
_space_group_IT_number           15
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-C 2yc'
_symmetry_space_group_name_H-M   'C 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                 117.380(5)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   24.2923(14)
_cell_length_b                   10.3638(4)
_cell_length_c                   15.5395(6)
_cell_measurement_reflns_used    4185
_cell_measurement_temperature    200(2)
_cell_measurement_theta_max      29.2128
_cell_measurement_theta_min      2.8606
_cell_volume                     3474.0(3)
_computing_cell_refinement
; 
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. 
;
_computing_data_collection
; 
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. 
;
_computing_data_reduction
; 
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. 
;
_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      200(2)
_diffrn_measured_fraction_theta_full 0.981
_diffrn_measured_fraction_theta_max 0.981
_diffrn_measurement_device_type  'Oxford Diffraction Gemini A'
_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  0.0311
_diffrn_reflns_av_sigmaI/netI    0.0280
_diffrn_reflns_limit_h_max       30
_diffrn_reflns_limit_h_min       -30
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_number            17368
_diffrn_reflns_theta_full        27.50
_diffrn_reflns_theta_max         27.50
_diffrn_reflns_theta_min         2.87
_exptl_absorpt_coefficient_mu    0.376
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.95373
_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_density_diffrn    1.355
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1464
_exptl_crystal_size_max          0.20
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.10
_refine_diff_density_max         0.292
_refine_diff_density_min         -0.361
_refine_diff_density_rms         0.042
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.016
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     242
_refine_ls_number_reflns         3931
_refine_ls_number_restraints     3
_refine_ls_restrained_S_all      1.019
_refine_ls_R_factor_all          0.0716
_refine_ls_R_factor_gt           0.0477
_refine_ls_shift/su_max          0.003
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0593P)²+2.7021P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1144
_refine_ls_wR_factor_ref         0.1305
_reflns_number_gt                2898
_reflns_number_total             3931
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ol502602t_si_003.cif
_cod_data_source_block           ic15845
_cod_depositor_comments
;
The following automatic conversions were performed:

'_symmetry_cell_setting' value 'Monoclinic' changed to 'monoclinic'
according to
/home/saulius/struct/COD-crude-data--automatic-downloads/rss-feeds/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 2827 2014-09-09 07:05:25Z andrius 

 Adding full bibliography for 1517974--1517975.cif.
;
_cod_original_sg_symbol_H-M      C2/c
_cod_database_code               1517974
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y, -z+1/2'
'x+1/2, y+1/2, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y, z-1/2'
'-x+1/2, -y+1/2, -z'
'x+1/2, -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
N1 N 0.04784(7) 0.65648(14) 0.20075(10) 0.0310(3) Uani 1 1 d . . .
N2 N -0.04071(6) 0.55718(13) 0.09931(9) 0.0280(3) Uani 1 1 d . . .
C1 C 0.03007(8) 0.32093(16) 0.24787(11) 0.0299(4) Uani 1 1 d . . .
C2 C 0.06716(9) 0.21092(18) 0.28247(13) 0.0399(4) Uani 1 1 d . . .
H2A H 0.0531 0.1415 0.3072 0.048 Uiso 1 1 calc R . .
C3 C 0.12358(10) 0.2001(2) 0.28171(15) 0.0475(5) Uani 1 1 d . . .
H3A H 0.1479 0.1244 0.3062 0.057 Uiso 1 1 calc R . .
C4 C 0.14456(9) 0.2994(2) 0.24532(14) 0.0451(5) Uani 1 1 d . . .
H4A H 0.1833 0.2925 0.2445 0.054 Uiso 1 1 calc R . .
C5 C 0.10883(8) 0.40878(19) 0.21013(12) 0.0368(4) Uani 1 1 d . . .
H5A H 0.1233 0.4770 0.1851 0.044 Uiso 1 1 calc R . .
C6 C 0.05166(8) 0.42119(16) 0.21058(11) 0.0288(4) Uani 1 1 d . . .
C7 C 0.01938(8) 0.54501(16) 0.17210(11) 0.0270(4) Uani 1 1 d . . .
C8 C 0.00509(8) 0.74843(16) 0.14434(12) 0.0302(4) Uani 1 1 d . . .
C9 C 0.01200(10) 0.88211(17) 0.14191(14) 0.0389(4) Uani 1 1 d . . .
H9A H 0.0493 0.9237 0.1857 0.047 Uiso 1 1 calc R . .
C10 C -0.03698(11) 0.95116(19) 0.07405(15) 0.0459(5) Uani 1 1 d . . .
H10A H -0.0332 1.0420 0.0702 0.055 Uiso 1 1 calc R . .
C11 C -0.09228(11) 0.89037(19) 0.01044(15) 0.0476(5) Uani 1 1 d . . .
H11A H -0.1252 0.9413 -0.0354 0.057 Uiso 1 1 calc R . .
C12 C -0.10051(9) 0.75849(18) 0.01220(13) 0.0386(4) Uani 1 1 d . . .
H12A H -0.1382 0.7176 -0.0309 0.046 Uiso 1 1 calc R . .
C13 C -0.05050(8) 0.68919(16) 0.08071(12) 0.0302(4) Uani 1 1 d . . .
C14 C -0.08449(8) 0.45799(16) 0.04794(11) 0.0287(4) Uani 1 1 d . . .
C15 C -0.14310(9) 0.46423(18) 0.04194(13) 0.0372(4) Uani 1 1 d . . .
H15A H -0.1534 0.5322 0.0730 0.045 Uiso 1 1 calc R . .
C16 C -0.18662(9) 0.3710(2) -0.00946(14) 0.0456(5) Uani 1 1 d . . .
H16A H -0.2271 0.3756 -0.0145 0.055 Uiso 1 1 calc R . .
C17 C -0.17131(10) 0.2708(2) -0.05367(14) 0.0461(5) Uani 1 1 d . . .
H17A H -0.2011 0.2062 -0.0884 0.055 Uiso 1 1 calc R . .
C18 C -0.11267(10) 0.26519(18) -0.04701(13) 0.0401(4) Uani 1 1 d . . .
H18A H -0.1022 0.1966 -0.0774 0.048 Uiso 1 1 calc R . .
C19 C -0.06898(9) 0.35872(17) 0.00361(12) 0.0321(4) Uani 1 1 d . . .
H19A H -0.0287 0.3548 0.0079 0.038 Uiso 1 1 calc R . .
Cl1 Cl 0.2142(3) 0.8938(5) 0.3081(6) 0.131(2) Uani 0.556(17) 1 d PD A 1
Cl2 Cl 0.24007(18) 0.6239(3) 0.3439(6) 0.0872(13) Uani 0.556(17) 1 d P A 1
Cl1' Cl 0.21123(19) 0.8951(5) 0.2918(3) 0.0610(12) Uani 0.444(17) 1 d P A 2
Cl2' Cl 0.2430(3) 0.6395(8) 0.3792(7) 0.1123(19) Uani 0.444(17) 1 d P A 2
C20 C 0.18954(14) 0.7560(4) 0.3355(3) 0.0867(9) Uani 1 1 d D . .
H1 H 0.1989(18) 0.780(3) 0.3959(15) 0.130 Uiso 1 1 d D . .
H2 H 0.1534(12) 0.730(4) 0.289(2) 0.130 Uiso 1 1 d 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'
N N 0.0061 0.0033 '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_3
C7 N1 C8 105.42(14) .
C7 N2 C13 105.92(14) .
C7 N2 C14 128.78(14) .
C13 N2 C14 125.23(14) .
C2 C1 C6 117.72(16) .
C2 C1 C1 116.99(12) 2
C6 C1 C1 125.28(12) 2
C3 C2 C1 121.98(18) .
C4 C3 C2 119.89(18) .
C5 C4 C3 119.47(18) .
C4 C5 C6 121.29(18) .
C5 C6 C1 119.65(16) .
C5 C6 C7 114.91(15) .
C1 C6 C7 125.43(15) .
N1 C7 N2 112.98(14) .
N1 C7 C6 121.80(15) .
N2 C7 C6 125.06(15) .
N1 C8 C13 110.18(14) .
N1 C8 C9 129.39(17) .
C13 C8 C9 120.37(17) .
C10 C9 C8 117.69(19) .
C9 C10 C11 121.28(18) .
C12 C11 C10 122.10(19) .
C11 C12 C13 116.23(19) .
C12 C13 N2 132.07(17) .
C12 C13 C8 122.31(16) .
N2 C13 C8 105.50(15) .
C19 C14 C15 120.55(16) .
C19 C14 N2 120.64(15) .
C15 C14 N2 118.80(15) .
C16 C15 C14 119.69(17) .
C15 C16 C17 120.09(19) .
C18 C17 C16 119.77(18) .
C17 C18 C19 120.53(18) .
C14 C19 C18 119.36(17) .
Cl2' C20 Cl1 114.6(3) .
Cl2' C20 Cl1' 115.5(3) .
Cl1 C20 Cl1' 6.9(3) .
Cl2' C20 Cl2 17.5(3) .
Cl1 C20 Cl2 110.7(3) .
Cl1' C20 Cl2 109.4(3) .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
N1 C7 1.314(2) .
N1 C8 1.385(2) .
N2 C7 1.381(2) .
N2 C13 1.396(2) .
N2 C14 1.430(2) .
C1 C2 1.398(2) .
C1 C6 1.404(2) .
C1 C1 1.492(3) 2
C2 C3 1.381(3) .
C3 C4 1.380(3) .
C4 C5 1.379(3) .
C5 C6 1.398(2) .
C6 C7 1.479(2) .
C8 C13 1.397(2) .
C8 C9 1.398(2) .
C9 C10 1.373(3) .
C10 C11 1.399(3) .
C11 C12 1.383(3) .
C12 C13 1.391(2) .
C14 C19 1.383(2) .
C14 C15 1.385(2) .
C15 C16 1.383(3) .
C16 C17 1.387(3) .
C17 C18 1.381(3) .
C18 C19 1.385(3) .
Cl1 C20 1.678(7) .
Cl2 C20 1.803(5) .
Cl1' C20 1.775(6) .
Cl2' C20 1.671(7) .
