#------------------------------------------------------------------------------
#$Date: 2016-02-21 02:03:34 +0200 (Sun, 21 Feb 2016) $
#$Revision: 176798 $
#$URL: svn://www.crystallography.net/cod/cif/2/23/29/2232979.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/. The original data for this entry
# were provided by IUCr Journals, http://journals.iucr.org/.
#
# The file may be used within the scientific community so long as
# proper attribution is given to the journal article from which the
# data were obtained.
#
data_2232979
loop_
_publ_author_name
'Wang, Haitao'
'Jia, Xiaoshi'
'Qu, Songnan'
'Bai, Binglian'
'Li, Min'
_publ_section_title
;
 5,5'-Bis(naphthalen-2-yl)-2,2'-bi(1,3,4-oxadiazole)
;
_journal_coeditor_code           VM2137
_journal_issue                   12
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o3360
_journal_paper_doi               10.1107/S1600536811048513
_journal_volume                  67
_journal_year                    2011
_chemical_formula_iupac          'C24 H14 N4 O2'
_chemical_formula_moiety         'C24 H14 N4 O2'
_chemical_formula_sum            'C24 H14 N4 O2'
_chemical_formula_weight         390.39
_chemical_name_systematic
;
5,5'-Bis(naphthalen-2-yl)-2,2'-bi(1,3,4-oxadiazole)
;
_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                 109.82(3)
_cell_angle_gamma                90.00
_cell_formula_units_Z            2
_cell_length_a                   7.8982(16)
_cell_length_b                   5.7107(11)
_cell_length_c                   21.503(5)
_cell_measurement_temperature    293(2)
_cell_volume                     912.4(4)
_computing_cell_refinement       'RAPID-AUTO (Rigaku, 1998)'
_computing_data_collection       'RAPID-AUTO (Rigaku, 1998)'
_computing_data_reduction        'CrystalStructure (Rigaku/MSC, 2002)'
_computing_molecular_graphics    'PLATON (Spek, 2009)'
_computing_publication_material  'SHELXL97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      293(2)
_diffrn_measured_fraction_theta_full 0.996
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measurement_device_type  'Rigaku R-AXIS RAPID'
_diffrn_measurement_method       'ω scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0297
_diffrn_reflns_av_sigmaI/netI    0.0267
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_l_max       27
_diffrn_reflns_limit_l_min       -27
_diffrn_reflns_number            8518
_diffrn_reflns_theta_full        27.48
_diffrn_reflns_theta_max         27.48
_diffrn_reflns_theta_min         3.71
_exptl_absorpt_coefficient_mu    0.094
_exptl_absorpt_correction_T_max  0.9888
_exptl_absorpt_correction_T_min  0.9833
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(ABSCOR; Higashi, 1995)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.421
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             404
_exptl_crystal_size_max          0.18
_exptl_crystal_size_mid          0.14
_exptl_crystal_size_min          0.12
_refine_diff_density_max         0.161
_refine_diff_density_min         -0.182
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.069
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     136
_refine_ls_number_reflns         2091
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.069
_refine_ls_R_factor_all          0.0571
_refine_ls_R_factor_gt           0.0386
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0577P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0993
_refine_ls_wR_factor_ref         0.1058
_reflns_number_gt                1468
_reflns_number_total             2091
_reflns_threshold_expression     I>2sigma(I)
_cod_data_source_file            vm2137.cif
_cod_data_source_block           I
_cod_original_cell_volume        912.4(3)
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               2232979
_cod_database_fobs_code          2232979
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_type_symbol
_atom_site_label
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_occupancy
_atom_site_symmetry_multiplicity
O O1 0.18040(11) 0.40921(16) 0.97102(4) 0.0412(2) Uani d . 1 1
N N1 0.01904(14) 0.7350(2) 0.94532(6) 0.0482(3) Uani d . 1 1
N N2 0.14392(14) 0.7347(2) 0.91193(6) 0.0479(3) Uani d . 1 1
C C1 0.04644(15) 0.5425(2) 0.97855(6) 0.0407(3) Uani d . 1 1
C C2 0.23461(16) 0.5413(2) 0.92839(6) 0.0388(3) Uani d . 1 1
C C3 0.38061(15) 0.4564(2) 0.90721(6) 0.0373(3) Uani d . 1 1
C C4 0.46713(17) 0.2407(2) 0.93102(6) 0.0448(3) Uani d . 1 1
H H4 0.4287 0.1499 0.9596 0.054 Uiso calc R 1 1
C C5 0.60641(17) 0.1660(2) 0.91221(7) 0.0453(3) Uani d . 1 1
H H5 0.6637 0.0256 0.9288 0.054 Uiso calc R 1 1
C C6 0.66520(15) 0.2993(2) 0.86777(6) 0.0389(3) Uani d . 1 1
C C7 0.80712(17) 0.2254(3) 0.84590(7) 0.0506(4) Uani d . 1 1
H H7 0.8681 0.0868 0.8621 0.061 Uiso calc R 1 1
C C8 0.85466(18) 0.3556(3) 0.80150(8) 0.0586(4) Uani d . 1 1
H H8 0.9466 0.3037 0.7870 0.070 Uiso calc R 1 1
C C9 0.76681(19) 0.5674(3) 0.77722(8) 0.0565(4) Uani d . 1 1
H H9 0.8008 0.6543 0.7468 0.068 Uiso calc R 1 1
C C10 0.63230(17) 0.6463(3) 0.79789(6) 0.0459(3) Uani d . 1 1
H H10 0.5763 0.7881 0.7821 0.055 Uiso calc R 1 1
C C11 0.57699(15) 0.5144(2) 0.84322(6) 0.0364(3) Uani d . 1 1
C C12 0.43475(15) 0.5888(2) 0.86414(6) 0.0379(3) Uani d . 1 1
H H12 0.3768 0.7297 0.8485 0.045 Uiso calc R 1 1
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_site_symmetry_3
_geom_angle
C1 O1 C2 . 101.84(10)
C1 N1 N2 . 105.54(11)
C2 N2 N1 . 106.25(11)
N1 C1 O1 . 113.78(11)
N1 C1 C1 3_567 127.93(15)
O1 C1 C1 3_567 118.28(15)
N2 C2 O1 . 112.58(11)
N2 C2 C3 . 128.24(12)
O1 C2 C3 . 119.18(12)
C12 C3 C4 . 120.03(11)
C12 C3 C2 . 119.22(12)
C4 C3 C2 . 120.75(12)
C5 C4 C3 . 120.24(12)
C5 C4 H4 . 119.9
C3 C4 H4 . 119.9
C4 C5 C6 . 120.93(13)
C4 C5 H5 . 119.5
C6 C5 H5 . 119.5
C5 C6 C7 . 122.68(13)
C5 C6 C11 . 118.86(11)
C7 C6 C11 . 118.45(12)
C8 C7 C6 . 120.48(14)
C8 C7 H7 . 119.8
C6 C7 H7 . 119.8
C7 C8 C9 . 120.87(14)
C7 C8 H8 . 119.6
C9 C8 H8 . 119.6
C10 C9 C8 . 120.39(14)
C10 C9 H9 . 119.8
C8 C9 H9 . 119.8
C9 C10 C11 . 120.50(14)
C9 C10 H10 . 119.8
C11 C10 H10 . 119.8
C12 C11 C10 . 121.71(12)
C12 C11 C6 . 119.00(11)
C10 C11 C6 . 119.29(11)
C3 C12 C11 . 120.93(12)
C3 C12 H12 . 119.5
C11 C12 H12 . 119.5
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_site_symmetry_2
_geom_bond_distance
O1 C1 . 1.3568(15)
O1 C2 . 1.3636(15)
N1 C1 . 1.2889(18)
N1 N2 . 1.4031(16)
N2 C2 . 1.2986(17)
C1 C1 3_567 1.443(3)
C2 C3 . 1.4588(17)
C3 C12 . 1.3714(17)
C3 C4 . 1.4175(18)
C4 C5 . 1.3629(19)
C4 H4 . 0.9300
C5 C6 . 1.4173(19)
C5 H5 . 0.9300
C6 C7 . 1.4190(17)
C6 C11 . 1.4228(18)
C7 C8 . 1.360(2)
C7 H7 . 0.9300
C8 C9 . 1.404(2)
C8 H8 . 0.9300
C9 C10 . 1.3600(19)
C9 H9 . 0.9300
C10 C11 . 1.4130(18)
C10 H10 . 0.9300
C11 C12 . 1.4098(17)
C12 H12 . 0.9300
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_site_symmetry_4
_geom_torsion
C1 N1 N2 C2 . 0.01(14)
N2 N1 C1 O1 . 0.15(15)
N2 N1 C1 C1 3_567 179.92(16)
C2 O1 C1 N1 . -0.23(14)
C2 O1 C1 C1 3_567 179.97(14)
N1 N2 C2 O1 . -0.16(14)
N1 N2 C2 C3 . -179.98(12)
C1 O1 C2 N2 . 0.24(13)
C1 O1 C2 C3 . -179.92(11)
N2 C2 C3 C12 . -0.4(2)
O1 C2 C3 C12 . 179.76(10)
N2 C2 C3 C4 . 179.09(12)
O1 C2 C3 C4 . -0.72(18)
C12 C3 C4 C5 . 1.19(19)
C2 C3 C4 C5 . -178.33(12)
C3 C4 C5 C6 . -1.2(2)
C4 C5 C6 C7 . -178.66(12)
C4 C5 C6 C11 . 0.41(19)
C5 C6 C7 C8 . 177.78(13)
C11 C6 C7 C8 . -1.28(19)
C6 C7 C8 C9 . 1.1(2)
C7 C8 C9 C10 . 0.1(2)
C8 C9 C10 C11 . -1.1(2)
C9 C10 C11 C12 . -178.28(12)
C9 C10 C11 C6 . 0.84(19)
C5 C6 C11 C12 . 0.36(17)
C7 C6 C11 C12 . 179.46(11)
C5 C6 C11 C10 . -178.78(11)
C7 C6 C11 C10 . 0.33(17)
C4 C3 C12 C11 . -0.42(18)
C2 C3 C12 C11 . 179.11(11)
C10 C11 C12 C3 . 178.77(11)
C6 C11 C12 C3 . -0.35(18)
