#------------------------------------------------------------------------------
#$Date: 2016-02-21 02:03:34 +0200 (Sun, 21 Feb 2016) $
#$Revision: 176798 $
#$URL: svn://www.crystallography.net/cod/cif/2/23/63/2236361.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_2236361
loop_
_publ_author_name
'Song, Man-Man'
'Wu, Kong-Li'
'Zhu, Lin'
'Zheng, Juan'
'Xu, Yan'
_publ_section_title
;
 5-Phenyl-1,3,4-oxadiazol-2-amine
;
_journal_coeditor_code           IM2386
_journal_issue                   10
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o3058
_journal_paper_doi               10.1107/S1600536812040640
_journal_volume                  68
_journal_year                    2012
_chemical_formula_iupac          'C8 H7 N3 O'
_chemical_formula_moiety         'C8 H7 N3 O'
_chemical_formula_sum            'C8 H7 N3 O'
_chemical_formula_weight         161.17
_chemical_name_systematic
;
5-Phenyl-1,3,4-oxadiazol-2-amine
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2ybc'
_space_group_name_H-M_alt        'P 1 21/c 1'
_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                 130.193(18)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   11.194(3)
_cell_length_b                   5.8990(5)
_cell_length_c                   15.034(5)
_cell_measurement_reflns_used    656
_cell_measurement_temperature    291(2)
_cell_measurement_theta_max      26.3094
_cell_measurement_theta_min      3.4485
_cell_volume                     758.3(4)
_computing_cell_refinement       'CrysAlis PRO (Agilent, 2011)'
_computing_data_collection       'CrysAlis PRO (Agilent, 2011)'
_computing_data_reduction        'CrysAlis PRO (Agilent, 2011)'
_computing_molecular_graphics
'OLEX2 (Dolomanov et al., 2009)'
_computing_publication_material
'OLEX2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      291.15
_diffrn_detector_area_resol_mean 16.2312
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device_type  'Agilent Xcalibur Eos Gemini'
_diffrn_measurement_method       'ω scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.7107
_diffrn_reflns_av_R_equivalents  0.0398
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_k_min       -4
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            2912
_diffrn_reflns_theta_full        26.35
_diffrn_reflns_theta_max         26.35
_diffrn_reflns_theta_min         3.55
_exptl_absorpt_coefficient_mu    0.099
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.85136
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
(CrysAlis PRO; Agilent, 2011)
;
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.412
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             336
_exptl_crystal_size_max          0.26
_exptl_crystal_size_mid          0.24
_exptl_crystal_size_min          0.22
_refine_diff_density_max         0.168
_refine_diff_density_min         -0.150
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.018
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     109
_refine_ls_number_reflns         1551
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.018
_refine_ls_R_factor_all          0.1158
_refine_ls_R_factor_gt           0.0556
_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)+(0.0540P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1098
_refine_ls_wR_factor_ref         0.1369
_reflns_number_gt                877
_reflns_number_total             1551
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            im2386.cif
_cod_data_source_block           I
_cod_original_cell_volume        758.3(3)
_cod_database_code               2236361
_cod_database_fobs_code          2236361
loop_
_space_group_symop_id
_space_group_symop_operation_xyz
1 'x, y, z'
2 '-x, y+1/2, -z+1/2'
3 '-x, -y, -z'
4 '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 -0.15541(17) 0.6145(2) 0.02276(13) 0.0495(5) Uani d . 1 1
N N1 -0.2177(2) 0.2637(3) -0.04164(18) 0.0617(7) Uani d . 1 1
N N2 -0.3435(2) 0.4062(3) -0.12624(17) 0.0594(7) Uani d . 1 1
N N3 -0.3795(2) 0.8025(3) -0.12550(17) 0.0622(7) Uani d . 1 1
H H3A -0.4628 0.8128 -0.2012 0.075 Uiso d R 1 1
H H3B -0.3161 0.9341 -0.0922 0.075 Uiso d R 1 1
C C1 0.1056(3) 0.1191(4) 0.1680(2) 0.0624(8) Uani d . 1 1
H H1 0.0506 0.0125 0.1084 0.075 Uiso calc R 1 1
C C2 0.2512(3) 0.0674(4) 0.2723(3) 0.0683(9) Uani d . 1 1
H H2 0.2942 -0.0749 0.2825 0.082 Uiso calc R 1 1
C C3 0.3329(3) 0.2221(5) 0.3606(2) 0.0714(9) Uani d . 1 1
H H3 0.4308 0.1850 0.4303 0.086 Uiso calc R 1 1
C C4 0.2704(3) 0.4311(5) 0.3463(2) 0.0720(9) Uani d . 1 1
H H4 0.3259 0.5365 0.4065 0.086 Uiso calc R 1 1
C C5 0.1250(3) 0.4866(4) 0.2428(2) 0.0578(8) Uani d . 1 1
H H5 0.0828 0.6292 0.2336 0.069 Uiso calc R 1 1
C C6 0.0423(3) 0.3320(4) 0.1532(2) 0.0457(6) Uani d . 1 1
C C7 -0.1115(3) 0.3912(4) 0.0434(2) 0.0450(6) Uani d . 1 1
C C8 -0.3014(3) 0.6083(4) -0.0839(2) 0.0477(7) Uani d . 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
C8 O1 C7 102.89(16)
C7 N1 N2 106.97(18)
C8 N2 N1 105.75(18)
H3A N3 H3B 115.3
C8 N3 H3A 119.2
C8 N3 H3B 114.6
C2 C1 H1 120.4
C2 C1 C6 119.2(2)
C6 C1 H1 120.4
C1 C2 H2 119.5
C3 C2 C1 121.0(2)
C3 C2 H2 119.5
C2 C3 H3 120.1
C4 C3 C2 119.8(3)
C4 C3 H3 120.1
C3 C4 H4 119.9
C3 C4 C5 120.2(2)
C5 C4 H4 119.9
C4 C5 H5 119.8
C6 C5 C4 120.3(2)
C6 C5 H5 119.8
C1 C6 C7 120.3(2)
C5 C6 C1 119.5(2)
C5 C6 C7 120.3(2)
O1 C7 C6 118.30(19)
N1 C7 O1 111.77(19)
N1 C7 C6 129.9(2)
N2 C8 O1 112.6(2)
N2 C8 N3 130.2(2)
N3 C8 O1 117.12(19)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
O1 C7 1.369(2)
O1 C8 1.364(3)
N1 N2 1.413(3)
N1 C7 1.285(3)
N2 C8 1.289(3)
N3 H3A 0.8936
N3 H3B 0.9476
N3 C8 1.328(3)
C1 H1 0.9300
C1 C2 1.382(3)
C1 C6 1.387(3)
C2 H2 0.9300
C2 C3 1.366(4)
C3 H3 0.9300
C3 C4 1.364(4)
C4 H4 0.9300
C4 C5 1.382(3)
C5 H5 0.9300
C5 C6 1.376(3)
C6 C7 1.464(3)
loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_site_symmetry_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
N3 H3A N2 2_454 0.89 2.12 2.997(3) 168.7
N3 H3B N1 1_565 0.95 2.12 3.054(3) 168.4
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
N1 N2 C8 O1 0.7(3)
N1 N2 C8 N3 -176.1(3)
N2 N1 C7 O1 -0.4(3)
N2 N1 C7 C6 -180.0(2)
C1 C2 C3 C4 0.1(5)
C1 C6 C7 O1 -166.5(2)
C1 C6 C7 N1 13.1(4)
C2 C1 C6 C5 -0.5(4)
C2 C1 C6 C7 179.8(3)
C2 C3 C4 C5 -0.1(5)
C3 C4 C5 C6 -0.2(4)
C4 C5 C6 C1 0.5(4)
C4 C5 C6 C7 -179.8(2)
C5 C6 C7 O1 13.9(3)
C5 C6 C7 N1 -166.5(3)
C6 C1 C2 C3 0.3(4)
C7 O1 C8 N2 -0.9(3)
C7 O1 C8 N3 176.4(2)
C7 N1 N2 C8 -0.2(3)
C8 O1 C7 N1 0.8(3)
C8 O1 C7 C6 -179.6(2)
