#------------------------------------------------------------------------------
#$Date: 2017-10-13 11:42:48 +0300 (Fri, 13 Oct 2017) $
#$Revision: 201978 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/22/57/2225715.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_2225715
loop_
_publ_author_name
'Fun, Hoong-Kun'
'Rosli, Mohd Mustaqim'
'Rai, Sankappa'
'Isloor, Arun M.'
'Shetty, Prakash'
_publ_section_title
;
 3-(2,4-Dichlorophenyl)-5-phenyl-1,2,4-oxadiazole
;
_journal_coeditor_code           SJ2743
_journal_issue                   4
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o851
_journal_paper_doi               10.1107/S160053681000927X
_journal_volume                  66
_journal_year                    2010
_chemical_formula_iupac          'C14 H8 Cl2 N2 O'
_chemical_formula_moiety         'C14 H8 Cl2 N2 O'
_chemical_formula_sum            'C14 H8 Cl2 N2 O'
_chemical_formula_weight         291.12
_chemical_name_systematic
;
3-(2,4-Dichlorophenyl)-5-phenyl-1,2,4-oxadiazole
;
_space_group_IT_number           2
_symmetry_cell_setting           triclinic
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                99.044(2)
_cell_angle_beta                 91.158(2)
_cell_angle_gamma                98.891(2)
_cell_formula_units_Z            2
_cell_length_a                   3.8035(2)
_cell_length_b                   10.9666(7)
_cell_length_c                   14.6949(9)
_cell_measurement_reflns_used    7625
_cell_measurement_temperature    100.0(10)
_cell_measurement_theta_max      36.01
_cell_measurement_theta_min      2.54
_cell_volume                     597.43(6)
_computing_cell_refinement       'SAINT (Bruker, 2005)'
_computing_data_collection       'APEX2 (Bruker, 2005)'
_computing_data_reduction        'SAINT (Bruker, 2005)'
_computing_molecular_graphics    'SHELXTL (Sheldrick, 2008)'
_computing_publication_material
'SHELXTL (Sheldrick, 2008) and PLATON (Spek, 2009)'
_computing_structure_refinement  'SHELXTL (Sheldrick, 2008)'
_computing_structure_solution    'SHELXTL (Sheldrick, 2008)'
_diffrn_ambient_temperature      100.0(10)
_diffrn_measured_fraction_theta_full 0.989
_diffrn_measured_fraction_theta_max 0.989
_diffrn_measurement_device_type
;
Bruker SMART APEXII CCD area-detector diffractometer
;
_diffrn_measurement_method       'φ and 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  0.0347
_diffrn_reflns_av_sigmaI/netI    0.0281
_diffrn_reflns_limit_h_max       4
_diffrn_reflns_limit_h_min       -4
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_number            12084
_diffrn_reflns_theta_full        27.49
_diffrn_reflns_theta_max         27.49
_diffrn_reflns_theta_min         1.40
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.534
_exptl_absorpt_correction_T_max  0.9531
_exptl_absorpt_correction_T_min  0.8093
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(SADABS; Bruker, 2005)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.618
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             296
_exptl_crystal_size_max          0.41
_exptl_crystal_size_mid          0.13
_exptl_crystal_size_min          0.09
_refine_diff_density_max         0.545
_refine_diff_density_min         -0.386
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.135
_refine_ls_hydrogen_treatment    refall
_refine_ls_matrix_type           full
_refine_ls_number_parameters     204
_refine_ls_number_reflns         2692
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.135
_refine_ls_R_factor_all          0.0428
_refine_ls_R_factor_gt           0.0352
_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)+(0.0727P)²+0.3227P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0963
_refine_ls_wR_factor_ref         0.1214
_reflns_number_gt                2355
_reflns_number_total             2692
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            sj2743.cif
_cod_data_source_block           I
_cod_depositor_comments
;
The following automatic conversions were performed:
'_symmetry_cell_setting' value 'Triclinic' changed to 'triclinic'
according to '/home/saulius/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 1527 2010-12-29 10:47:43Z saulius 
;
_cod_database_code               2225715
_cod_database_fobs_code          2225715
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -z'
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_disorder_assembly
_atom_site_disorder_group
Cl Cl1 0.67894(14) 0.17290(4) 0.56305(3) 0.02303(17) Uani d . 1 . .
Cl Cl2 0.74585(13) 0.52050(4) 0.34575(3) 0.01905(16) Uani d . 1 . .
O O1 1.0808(4) 0.40239(12) 0.07273(9) 0.0188(3) Uani d . 1 . .
N N1 1.1293(4) 0.22993(14) 0.12866(10) 0.0152(3) Uani d . 1 . .
N N2 0.9704(5) 0.42193(15) 0.16440(11) 0.0186(3) Uani d . 1 . .
C C1 1.3840(5) 0.31992(18) -0.09742(13) 0.0182(4) Uani d . 1 . .
C C2 1.5167(6) 0.27272(19) -0.18064(13) 0.0207(4) Uani d . 1 . .
C C3 1.5623(5) 0.14861(19) -0.19917(13) 0.0197(4) Uani d . 1 . .
C C4 1.4763(5) 0.06975(18) -0.13435(12) 0.0180(4) Uani d . 1 . .
C C5 1.3476(5) 0.11647(17) -0.05099(12) 0.0157(4) Uani d . 1 . .
C C6 1.3013(5) 0.24188(17) -0.03204(12) 0.0146(4) Uani d . 1 . .
C C7 1.1707(5) 0.28734(17) 0.05746(12) 0.0152(4) Uani d . 1 . .
C C8 1.0052(5) 0.31698(17) 0.19311(12) 0.0141(4) Uani d . 1 . .
C C9 0.9255(5) 0.28872(16) 0.28577(12) 0.0146(4) Uani d . 1 . .
C C10 0.9670(5) 0.16979(17) 0.30360(12) 0.0155(4) Uani d . 1 . .
C C11 0.8962(5) 0.13252(18) 0.38802(13) 0.0172(4) Uani d . 1 . .
C C12 0.7795(5) 0.21663(18) 0.45703(12) 0.0171(4) Uani d . 1 . .
C C13 0.7382(5) 0.33600(18) 0.44337(12) 0.0172(4) Uani d . 1 . .
C C14 0.8094(5) 0.37087(16) 0.35794(12) 0.0155(4) Uani d . 1 . .
H H1A 1.360(7) 0.402(3) -0.0859(17) 0.026(6) Uiso d . 1 . .
H H2A 1.572(7) 0.323(2) -0.2233(18) 0.024(6) Uiso d . 1 . .
H H3A 1.664(7) 0.121(2) -0.2558(18) 0.029(7) Uiso d . 1 . .
H H4A 1.483(6) -0.015(2) -0.1458(15) 0.015(5) Uiso d . 1 . .
H H5A 1.325(7) 0.068(2) -0.0091(17) 0.020(6) Uiso d . 1 . .
H H10A 1.028(7) 0.109(2) 0.2564(16) 0.019(6) Uiso d . 1 . .
H H11A 0.922(6) 0.054(2) 0.3967(15) 0.014(5) Uiso d . 1 . .
H H13A 0.635(7) 0.390(2) 0.4924(17) 0.022(6) Uiso d . 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'
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_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle
_geom_angle_publ_flag
C7 O1 N2 . . 106.71(14) ?
C7 N1 C8 . . 102.57(15) ?
C8 N2 O1 . . 103.00(15) ?
C2 C1 C6 . . 119.53(18) ?
C2 C1 H1A . . 119.2(16) ?
C6 C1 H1A . . 121.2(16) ?
C3 C2 C1 . . 120.30(17) ?
C3 C2 H2A . . 119.8(16) ?
C1 C2 H2A . . 119.9(16) ?
C2 C3 C4 . . 120.40(18) ?
C2 C3 H3A . . 117.6(16) ?
C4 C3 H3A . . 122.0(16) ?
C5 C4 C3 . . 119.60(18) ?
C5 C4 H4A . . 116.9(14) ?
C3 C4 H4A . . 123.3(14) ?
C4 C5 C6 . . 120.14(17) ?
C4 C5 H5A . . 117.2(16) ?
C6 C5 H5A . . 122.2(16) ?
C1 C6 C5 . . 120.04(17) ?
C1 C6 C7 . . 121.86(17) ?
C5 C6 C7 . . 118.10(16) ?
N1 C7 O1 . . 113.04(16) ?
N1 C7 C6 . . 127.93(16) ?
O1 C7 C6 . . 119.03(16) ?
N2 C8 N1 . . 114.69(16) ?
N2 C8 C9 . . 125.14(17) ?
N1 C8 C9 . . 120.17(15) ?
C10 C9 C14 . . 117.16(16) ?
C10 C9 C8 . . 117.41(16) ?
C14 C9 C8 . . 125.43(16) ?
C11 C10 C9 . . 122.41(17) ?
C11 C10 H10A . . 116.9(14) ?
C9 C10 H10A . . 120.5(14) ?
C10 C11 C12 . . 118.35(17) ?
C10 C11 H11A . . 120.0(14) ?
C12 C11 H11A . . 121.6(14) ?
C13 C12 C11 . . 121.57(17) ?
C13 C12 Cl1 . . 118.49(15) ?
C11 C12 Cl1 . . 119.94(15) ?
C12 C13 C14 . . 118.95(17) ?
C12 C13 H13A . . 118.8(14) ?
C14 C13 H13A . . 121.9(14) ?
C13 C14 C9 . . 121.56(17) ?
C13 C14 Cl2 . . 116.22(14) ?
C9 C14 Cl2 . . 122.21(14) ?
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_site_symmetry_2
_geom_bond_distance
_geom_bond_publ_flag
Cl1 C12 . 1.7338(18) ?
Cl2 C14 . 1.7310(18) ?
O1 C7 . 1.344(2) ?
O1 N2 . 1.413(2) ?
N1 C7 . 1.303(2) ?
N1 C8 . 1.380(2) ?
N2 C8 . 1.311(2) ?
C1 C2 . 1.387(3) ?
C1 C6 . 1.394(2) ?
C1 H1A . 0.91(3) ?
C2 C3 . 1.384(3) ?
C2 H2A . 0.91(3) ?
C3 C4 . 1.395(3) ?
C3 H3A . 0.95(3) ?
C4 C5 . 1.381(3) ?
C4 H4A . 0.92(2) ?
C5 C6 . 1.399(3) ?
C5 H5A . 0.87(2) ?
C6 C7 . 1.457(2) ?
C8 C9 . 1.470(2) ?
C9 C10 . 1.401(3) ?
C9 C14 . 1.405(3) ?
C10 C11 . 1.385(3) ?
C10 H10A . 0.94(2) ?
C11 C12 . 1.388(3) ?
C11 H11A . 0.91(2) ?
C12 C13 . 1.387(3) ?
C13 C14 . 1.389(3) ?
C13 H13A . 0.99(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
_geom_hbond_publ_flag
C3 H3A Cl1 1_654 0.95(3) 2.81(3) 3.577(2) 138.6(19) yes
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_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion
_geom_torsion_publ_flag
C7 O1 N2 C8 . . . . -0.24(19) ?
C6 C1 C2 C3 . . . . 0.8(3) ?
C1 C2 C3 C4 . . . . -0.2(3) ?
C2 C3 C4 C5 . . . . -0.5(3) ?
C3 C4 C5 C6 . . . . 0.5(3) ?
C2 C1 C6 C5 . . . . -0.9(3) ?
C2 C1 C6 C7 . . . . 178.25(17) ?
C4 C5 C6 C1 . . . . 0.2(3) ?
C4 C5 C6 C7 . . . . -178.94(17) ?
C8 N1 C7 O1 . . . . -0.2(2) ?
C8 N1 C7 C6 . . . . 179.12(18) ?
N2 O1 C7 N1 . . . . 0.3(2) ?
N2 O1 C7 C6 . . . . -179.11(15) ?
C1 C6 C7 N1 . . . . -169.98(19) ?
C5 C6 C7 N1 . . . . 9.1(3) ?
C1 C6 C7 O1 . . . . 9.4(3) ?
C5 C6 C7 O1 . . . . -171.53(16) ?
O1 N2 C8 N1 . . . . 0.1(2) ?
O1 N2 C8 C9 . . . . 179.68(16) ?
C7 N1 C8 N2 . . . . 0.1(2) ?
C7 N1 C8 C9 . . . . -179.53(16) ?
N2 C8 C9 C10 . . . . 177.93(18) ?
N1 C8 C9 C10 . . . . -2.5(3) ?
N2 C8 C9 C14 . . . . -1.8(3) ?
N1 C8 C9 C14 . . . . 177.79(17) ?
C14 C9 C10 C11 . . . . 0.4(3) ?
C8 C9 C10 C11 . . . . -179.33(17) ?
C9 C10 C11 C12 . . . . 0.1(3) ?
C10 C11 C12 C13 . . . . -0.9(3) ?
C10 C11 C12 Cl1 . . . . 178.69(14) ?
C11 C12 C13 C14 . . . . 1.2(3) ?
Cl1 C12 C13 C14 . . . . -178.38(14) ?
C12 C13 C14 C9 . . . . -0.7(3) ?
C12 C13 C14 Cl2 . . . . 179.14(14) ?
C10 C9 C14 C13 . . . . -0.1(3) ?
C8 C9 C14 C13 . . . . 179.63(17) ?
C10 C9 C14 Cl2 . . . . -179.90(14) ?
C8 C9 C14 Cl2 . . . . -0.2(3) ?
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 9635338
