#------------------------------------------------------------------------------
#$Date: 2016-03-26 17:05:35 +0200 (Sat, 26 Mar 2016) $
#$Revision: 180373 $
#$URL: svn://www.crystallography.net/cod/cif/7/20/42/7204228.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_7204228
loop_
_publ_author_name
'Wang, Changsheng'
'Jung, Gun-Young'
'Batsanov, Andrei S.'
'Bryce, Martin R.'
'Petty, Michael C.'
_publ_section_title
;
 New electron-transporting materials for light emitting diodes:
 1,3,4-oxadiazole--pyridine and 1,3,4-oxadiazole--pyrimidine hybrids
;
_journal_issue                   2
_journal_name_full               'Journal of Materials Chemistry'
_journal_page_first              173
_journal_paper_doi               10.1039/b106907c
_journal_volume                  12
_journal_year                    2002
_chemical_formula_sum            'C29 H29 N5 O2'
_chemical_formula_weight         479.57
_chemical_melting_point          490.1(6)
_chemical_name_systematic
; 
2,4-bis[2-(4-tert-butylphenyl)-1,3,4-oxadiazol-5-yl]pyridine
;
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2ybc'
_symmetry_space_group_name_H-M   'P 1 21/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                 90.221(4)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   18.7544(12)
_cell_length_b                   11.6181(7)
_cell_length_c                   11.4838(7)
_cell_measurement_reflns_used    870
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      23.0
_cell_measurement_theta_min      12.0
_cell_volume                     2502.2(3)
_computing_cell_refinement       'Bruker SMART'
_computing_data_collection       'Bruker SMART'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      100(2)
_diffrn_detector_area_resol_mean 8
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measurement_device_type  'SMART 1K CCD area detector'
_diffrn_measurement_method       'ω scans'
_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  0.0605
_diffrn_reflns_av_sigmaI/netI    0.0377
_diffrn_reflns_limit_h_max       24
_diffrn_reflns_limit_h_min       -24
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            27560
_diffrn_reflns_theta_full        27.50
_diffrn_reflns_theta_max         27.50
_diffrn_reflns_theta_min         2.06
_diffrn_standards_decay_%        0
_diffrn_standards_interval_count 0
_diffrn_standards_interval_time  0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.082
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.273
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    .
_exptl_crystal_description       shapeless
_exptl_crystal_F_000             1016
_exptl_crystal_size_max          0.35
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.15
_refine_diff_density_max         0.312
_refine_diff_density_min         -0.295
_refine_diff_density_rms         0.050
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.062
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     337
_refine_ls_number_reflns         5747
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.062
_refine_ls_R_factor_all          0.0660
_refine_ls_R_factor_gt           0.0465
_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)+(0.0425P)²+1.2996P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1052
_refine_ls_wR_factor_ref         0.1176
_reflns_number_gt                4388
_reflns_number_total             5747
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            b106907c.txt
_cod_data_source_block           2g
_cod_depositor_comments
;
The following automatic conversions were performed:
'_symmetry_cell_setting' value 'Monoclinic' changed to 'monoclinic'
according to '/home/adriana/struct/CIF-dictionaries/cif_core.dic'
dictionary named 'cif_core.dic' version 2.4.1 from 2010-06-29.

Automatic conversion script
Id: cif_fix_enum 1555 2011-01-17 13:19:09Z saulius 

The following automatic conversions were performed:

'_chemical_melting_point' value '216.3--217.6\% C' was changed to
'490.1(6)' - it was converted from degrees Celsius(C) to Kelvins(K),
the average value was taken and precision was estimated.

Automatic conversion script
Id: cif_fix_values 1569 2011-02-09 13:29:24Z adriana 
;
_cod_original_sg_symbol_H-M      P2(1)/c
_cod_database_code               7204228
#BEGIN Tags that were not found in dictionaries:
_ccdc_comments                   'light-emitting diode material'
#END Tags that were not found in dictionaries
loop_
_symmetry_equiv_pos_as_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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
N1 N 0.70873(7) 0.13061(12) 0.81720(12) 0.0238(3) Uani 1 1 d . . .
N2 N 0.75618(7) 0.12241(12) 0.91202(12) 0.0241(3) Uani 1 1 d . . .
N3 N 0.54624(7) 0.10577(12) 0.43169(12) 0.0234(3) Uani 1 1 d . . .
N4 N 0.50106(7) 0.08399(12) 0.33610(12) 0.0229(3) Uani 1 1 d . . .
O1 O 0.74469(6) 0.30614(9) 0.86354(9) 0.0195(2) Uani 1 1 d . . .
O2 O 0.50488(6) 0.27231(9) 0.36597(9) 0.0192(2) Uani 1 1 d . . .
C1 C 0.65688(8) 0.41073(13) 0.70138(13) 0.0223(3) Uani 0.50 1 d P A 1
H1 H 0.6819 0.4545 0.7556 0.027 Uiso 0.50 1 d PR A 1
N1C N 0.65688(8) 0.41073(13) 0.70138(13) 0.0223(3) Uani 0.50 1 d P A 2
C2 C 0.66088(8) 0.29417(14) 0.70077(13) 0.0194(3) Uani 1 1 d . . .
C3 C 0.62533(8) 0.22683(14) 0.61860(13) 0.0199(3) Uani 1 1 d . A .
H3 H 0.6289 0.1470 0.6194 0.024 Uiso 1 1 d R . .
C4 C 0.58404(8) 0.28324(13) 0.53463(13) 0.0191(3) Uani 1 1 d . . .
C5 C 0.57756(8) 0.40113(13) 0.53491(13) 0.0247(3) Uani 0.50 1 d P A 2
H5 H 0.5492 0.4391 0.4804 0.030 Uiso 0.50 1 d PR A 2
N5 N 0.57756(8) 0.40113(13) 0.53491(13) 0.0247(3) Uani 0.50 1 d P A 1
C6 C 0.61473(10) 0.46063(15) 0.61922(15) 0.0274(4) Uani 1 1 d . . .
H6 H 0.6106 0.5404 0.6199 0.033 Uiso 1 1 d R A .
C7 C 0.70394(8) 0.23868(14) 0.79210(13) 0.0193(3) Uani 1 1 d . A .
C8 C 0.77564(8) 0.22697(13) 0.93551(14) 0.0193(3) Uani 1 1 d . . .
C9 C 0.54622(8) 0.21595(13) 0.44572(13) 0.0192(3) Uani 1 1 d . A .
C10 C 0.47826(8) 0.18333(13) 0.30077(13) 0.0183(3) Uani 1 1 d . . .
C11 C 0.82595(8) 0.26802(13) 1.02390(13) 0.0188(3) Uani 1 1 d . . .
C12 C 0.85553(8) 0.37828(14) 1.01494(14) 0.0209(3) Uani 1 1 d . . .
H12 H 0.8422 0.4264 0.9539 0.025 Uiso 1 1 d R . .
C13 C 0.90445(8) 0.41598(13) 1.09701(14) 0.0207(3) Uani 1 1 d . . .
H13 H 0.9236 0.4895 1.0899 0.025 Uiso 1 1 d R . .
C14 C 0.92597(8) 0.34633(13) 1.19040(14) 0.0190(3) Uani 1 1 d . . .
C15 C 0.89560(8) 0.23657(14) 1.19824(14) 0.0208(3) Uani 1 1 d . . .
H15 H 0.9085 0.1887 1.2597 0.025 Uiso 1 1 d R . .
C16 C 0.84636(8) 0.19738(14) 1.11642(14) 0.0207(3) Uani 1 1 d . . .
H16 H 0.8272 0.1239 1.1234 0.025 Uiso 1 1 d R . .
C17 C 0.98056(9) 0.39254(14) 1.27890(14) 0.0216(3) Uani 1 1 d . . .
C18 C 1.00193(9) 0.30288(15) 1.37075(15) 0.0273(4) Uani 1 1 d . . .
H18A H 0.9606 0.2801 1.4141 0.034(3) Uiso 1 1 d R . .
H18B H 1.0366 0.3357 1.4227 0.034(3) Uiso 1 1 d R . .
H18C H 1.0220 0.2368 1.3329 0.034(3) Uiso 1 1 d R . .
C19 C 0.94806(10) 0.49795(15) 1.34135(15) 0.0290(4) Uani 1 1 d . . .
H19A H 0.9344 0.5545 1.2846 0.039(3) Uiso 1 1 d R . .
H19B H 0.9828 0.5304 1.3935 0.039(3) Uiso 1 1 d R . .
H19C H 0.9069 0.4745 1.3846 0.039(3) Uiso 1 1 d R . .
C20 C 1.04824(9) 0.42912(17) 1.21334(16) 0.0312(4) Uani 1 1 d . . .
H20A H 1.0677 0.3639 1.1731 0.036(3) Uiso 1 1 d R . .
H20B H 1.0828 0.4580 1.2679 0.036(3) Uiso 1 1 d R . .
H20C H 1.0365 0.4883 1.1581 0.036(3) Uiso 1 1 d R . .
C21 C 0.42836(8) 0.20933(13) 0.20637(13) 0.0173(3) Uani 1 1 d . . .
C22 C 0.42286(8) 0.31965(13) 0.15970(14) 0.0204(3) Uani 1 1 d . . .
H22 H 0.4538 0.3773 0.1843 0.024 Uiso 1 1 d R . .
C23 C 0.37096(8) 0.34379(13) 0.07657(14) 0.0207(3) Uani 1 1 d . . .
H23 H 0.3687 0.4172 0.0444 0.025 Uiso 1 1 d R . .
C24 C 0.32208(8) 0.26006(14) 0.03983(13) 0.0187(3) Uani 1 1 d . . .
C25 C 0.33001(8) 0.14879(13) 0.08523(13) 0.0199(3) Uani 1 1 d . . .
H25 H 0.2991 0.0910 0.0607 0.024 Uiso 1 1 d R . .
C26 C 0.38263(8) 0.12274(13) 0.16558(13) 0.0195(3) Uani 1 1 d . . .
H26 H 0.3877 0.0477 0.1925 0.023 Uiso 1 1 d R . .
C27 C 0.25877(9) 0.28863(15) -0.04050(14) 0.0232(4) Uani 1 1 d . . .
C28 C 0.19068(9) 0.28673(18) 0.03441(16) 0.0313(4) Uani 1 1 d . . .
H28A H 0.1842 0.2114 0.0670 0.032(3) Uiso 1 1 d R . .
H28B H 0.1503 0.3059 -0.0133 0.032(3) Uiso 1 1 d R . .
H28C H 0.1952 0.3420 0.0961 0.032(3) Uiso 1 1 d R . .
C29 C 0.26603(10) 0.40824(16) -0.09544(16) 0.0302(4) Uani 1 1 d . . .
H29A H 0.2665 0.4656 -0.0353 0.037(3) Uiso 1 1 d R . .
H29B H 0.2264 0.4217 -0.1468 0.037(3) Uiso 1 1 d R . .
H29C H 0.3096 0.4123 -0.1387 0.037(3) Uiso 1 1 d R . .
C30 C 0.25153(10) 0.19922(16) -0.13878(15) 0.0290(4) Uani 1 1 d . . .
H30A H 0.2941 0.1990 -0.1849 0.032(3) Uiso 1 1 d R . .
H30B H 0.2114 0.2186 -0.1871 0.032(3) Uiso 1 1 d R . .
H30C H 0.2445 0.1243 -0.1055 0.032(3) Uiso 1 1 d R . .
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'
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
_geom_angle_publ_flag
C7 N1 N2 106.37(13) . . ?
C8 N2 N1 105.92(13) . . ?
C9 N3 N4 105.99(13) . . ?
C10 N4 N3 106.33(13) . . ?
C8 O1 C7 102.28(12) . . ?
C9 O2 C10 102.10(12) . . ?
C2 C1 C6 117.04(14) . . ?
C1 C2 C3 122.52(15) . . ?
C1 C2 C7 117.67(14) . . ?
C3 C2 C7 119.80(14) . . ?
C2 C3 C4 117.79(14) . . ?
C5 C4 C3 120.95(14) . . ?
C5 C4 C9 119.34(14) . . ?
C3 C4 C9 119.70(14) . . ?
C4 C5 C6 117.20(15) . . ?
C1 C6 C5 124.45(16) . . ?
N1 C7 O1 112.67(14) . . ?
N1 C7 C2 128.55(14) . . ?
O1 C7 C2 118.77(14) . . ?
N2 C8 O1 112.76(14) . . ?
N2 C8 C11 129.05(14) . . ?
O1 C8 C11 118.17(13) . . ?
N3 C9 O2 113.11(13) . . ?
N3 C9 C4 127.98(14) . . ?
O2 C9 C4 118.90(13) . . ?
N4 C10 O2 112.46(13) . . ?
N4 C10 C21 128.78(14) . . ?
O2 C10 C21 118.74(13) . . ?
C16 C11 C12 119.13(14) . . ?
C16 C11 C8 120.72(14) . . ?
C12 C11 C8 120.13(14) . . ?
C13 C12 C11 120.09(15) . . ?
C12 C13 C14 121.77(15) . . ?
C15 C14 C13 117.34(14) . . ?
C15 C14 C17 123.09(14) . . ?
C13 C14 C17 119.57(14) . . ?
C16 C15 C14 121.58(15) . . ?
C15 C16 C11 120.08(15) . . ?
C18 C17 C14 112.89(13) . . ?
C18 C17 C20 108.06(14) . . ?
C14 C17 C20 108.77(13) . . ?
C18 C17 C19 108.74(14) . . ?
C14 C17 C19 108.71(13) . . ?
C20 C17 C19 109.62(14) . . ?
C22 C21 C26 119.19(14) . . ?
C22 C21 C10 121.46(14) . . ?
C26 C21 C10 119.28(14) . . ?
C23 C22 C21 120.05(14) . . ?
C22 C23 C24 121.53(14) . . ?
C23 C24 C25 117.39(14) . . ?
C23 C24 C27 122.28(14) . . ?
C25 C24 C27 120.20(14) . . ?
C26 C25 C24 121.66(14) . . ?
C25 C26 C21 120.03(14) . . ?
C29 C27 C24 111.91(14) . . ?
C29 C27 C30 108.53(14) . . ?
C24 C27 C30 111.10(13) . . ?
C29 C27 C28 108.52(14) . . ?
C24 C27 C28 107.54(13) . . ?
C30 C27 C28 109.17(14) . . ?
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
N1 C7 1.291(2) . ?
N1 N2 1.4069(18) . ?
N2 C8 1.296(2) . ?
N3 C9 1.290(2) . ?
N3 N4 1.4071(18) . ?
N4 C10 1.295(2) . ?
O1 C8 1.3647(19) . ?
O1 C7 1.3663(18) . ?
O2 C9 1.3649(18) . ?
O2 C10 1.3695(18) . ?
C1 C2 1.356(2) . ?
C1 C6 1.359(2) . ?
C2 C3 1.394(2) . ?
C2 C7 1.470(2) . ?
C3 C4 1.398(2) . ?
C4 C5 1.375(2) . ?
C4 C9 1.467(2) . ?
C5 C6 1.377(2) . ?
C8 C11 1.463(2) . ?
C10 C21 1.461(2) . ?
C11 C16 1.395(2) . ?
C11 C12 1.400(2) . ?
C12 C13 1.384(2) . ?
C13 C14 1.402(2) . ?
C14 C15 1.400(2) . ?
C14 C17 1.537(2) . ?
C15 C16 1.392(2) . ?
C17 C18 1.535(2) . ?
C17 C20 1.538(2) . ?
C17 C19 1.546(2) . ?
C21 C22 1.393(2) . ?
C21 C26 1.401(2) . ?
C22 C23 1.389(2) . ?
C23 C24 1.401(2) . ?
C24 C25 1.402(2) . ?
C24 C27 1.537(2) . ?
C25 C26 1.382(2) . ?
C27 C29 1.532(2) . ?
C27 C30 1.539(2) . ?
C27 C28 1.543(2) . ?
