#------------------------------------------------------------------------------
#$Date: 2017-10-13 11:42:48 +0300 (Fri, 13 Oct 2017) $
#$Revision: 201978 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/22/57/2225799.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_2225799
loop_
_publ_author_name
'Fun, Hoong-Kun'
'Rosli, Mohd Mustaqim'
'Rai, Sankappa'
'Isloor, Arun M.'
'Shetty, Prakash'
_publ_section_title
;
 5-(2,4-Dichlorophenyl)-3-(4-nitrophenyl)-1,2,4-oxadiazole
;
_journal_coeditor_code           CI5063
_journal_issue                   5
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o1196
_journal_page_last               o1197
_journal_paper_doi               10.1107/S1600536810011153
_journal_volume                  66
_journal_year                    2010
_chemical_formula_iupac          'C14 H7 Cl2 N3 O3'
_chemical_formula_moiety         'C14 H7 Cl2 N3 O3'
_chemical_formula_sum            'C14 H7 Cl2 N3 O3'
_chemical_formula_weight         336.13
_chemical_name_systematic
;
5-(2,4-Dichlorophenyl)-3-(4-nitrophenyl)-1,2,4-oxadiazole
;
_space_group_IT_number           29
_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_Hall  'P 2c -2ac'
_symmetry_space_group_name_H-M   'P c a 21'
_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                 90.00
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   13.5272(5)
_cell_length_b                   6.5362(2)
_cell_length_c                   15.6880(5)
_cell_measurement_reflns_used    2389
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      30.07
_cell_measurement_theta_min      2.60
_cell_volume                     1387.08(8)
_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      296(2)
_diffrn_measured_fraction_theta_full 0.996
_diffrn_measured_fraction_theta_max 0.996
_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  0.0451
_diffrn_reflns_av_sigmaI/netI    0.0449
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            9845
_diffrn_reflns_theta_full        26.00
_diffrn_reflns_theta_max         26.00
_diffrn_reflns_theta_min         2.60
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.484
_exptl_absorpt_correction_T_max  0.9800
_exptl_absorpt_correction_T_min  0.8428
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(SADABS; Bruker, 2005)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.610
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       plate
_exptl_crystal_F_000             680
_exptl_crystal_size_max          0.37
_exptl_crystal_size_mid          0.11
_exptl_crystal_size_min          0.04
_refine_diff_density_max         0.244
_refine_diff_density_min         -0.223
_refine_ls_abs_structure_details 'Flack (1983), 1243 Friedel pairs'
_refine_ls_abs_structure_Flack   -0.01(7)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.061
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     199
_refine_ls_number_reflns         2658
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.061
_refine_ls_R_factor_all          0.0690
_refine_ls_R_factor_gt           0.0484
_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)+(0.0361P)²+0.1623P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0842
_refine_ls_wR_factor_ref         0.0912
_reflns_number_gt                2029
_reflns_number_total             2658
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            ci5063.cif
_cod_data_source_block           I
_cod_depositor_comments
;
The following automatic conversions were performed:
'_symmetry_cell_setting' value 'Orthorhombic' changed to 'orthorhombic'
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               2225799
_cod_database_fobs_code          2225799
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, z+1/2'
'x+1/2, -y, z'
'-x+1/2, y, 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_disorder_assembly
_atom_site_disorder_group
Cl Cl1 0.37074(7) 1.17134(15) 0.20371(7) 0.0672(3) Uani d . 1 . .
Cl Cl2 0.08039(7) 0.73697(16) 0.34239(10) 0.0814(4) Uani d . 1 . .
O O1 0.15793(17) 0.3687(4) 0.41360(18) 0.0643(8) Uani d . 1 . .
O O2 0.3673(2) -0.6615(5) 0.6679(2) 0.0975(12) Uani d . 1 . .
O O3 0.5067(2) -0.5915(5) 0.6109(2) 0.0959(11) Uani d . 1 . .
N N1 0.1636(2) 0.1879(5) 0.4615(2) 0.0653(10) Uani d . 1 . .
N N2 0.3154(2) 0.2966(4) 0.4278(2) 0.0454(7) Uani d . 1 . .
N N3 0.4200(3) -0.5541(5) 0.6249(2) 0.0646(9) Uani d . 1 . .
C C1 0.3731(2) 0.6429(5) 0.3289(2) 0.0515(10) Uani d . 1 . .
H H1A 0.4198 0.5472 0.3463 0.062 Uiso calc R 1 . .
C C2 0.4043(3) 0.8143(5) 0.2848(3) 0.0562(10) Uani d . 1 . .
H H2A 0.4709 0.8346 0.2729 0.067 Uiso calc R 1 . .
C C3 0.3342(3) 0.9546(5) 0.2589(2) 0.0478(9) Uani d . 1 . .
C C4 0.2351(3) 0.9269(5) 0.2767(2) 0.0493(9) Uani d . 1 . .
H H4A 0.1888 1.0233 0.2594 0.059 Uiso calc R 1 . .
C C5 0.2060(2) 0.7551(5) 0.3204(2) 0.0484(9) Uani d . 1 . .
C C6 0.2735(2) 0.6087(4) 0.3481(2) 0.0417(8) Uani d . 1 . .
C C7 0.2522(2) 0.4235(5) 0.3964(2) 0.0423(8) Uani d . 1 . .
C C8 0.2581(3) 0.1536(5) 0.4676(2) 0.0434(8) Uani d . 1 . .
C C9 0.2984(2) -0.0278(5) 0.5105(2) 0.0411(8) Uani d . 1 . .
C C10 0.2372(2) -0.1701(5) 0.5499(2) 0.0463(9) Uani d . 1 . .
H H10A 0.1692 -0.1493 0.5501 0.056 Uiso calc R 1 . .
C C11 0.2759(3) -0.3416(5) 0.5887(2) 0.0491(10) Uani d . 1 . .
H H11A 0.2350 -0.4357 0.6158 0.059 Uiso calc R 1 . .
C C12 0.3767(3) -0.3693(5) 0.5861(2) 0.0457(9) Uani d . 1 . .
C C13 0.4388(3) -0.2323(5) 0.5472(2) 0.0547(10) Uani d . 1 . .
H H13A 0.5066 -0.2559 0.5458 0.066 Uiso calc R 1 . .
C C14 0.3995(2) -0.0590(5) 0.5103(2) 0.0508(9) Uani d . 1 . .
H H14A 0.4411 0.0369 0.4851 0.061 Uiso calc R 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 N1 . . 106.2(2) ?
C8 N1 O1 . . 103.8(3) ?
C7 N2 C8 . . 103.8(3) ?
O2 N3 O3 . . 123.6(4) ?
O2 N3 C12 . . 118.2(3) ?
O3 N3 C12 . . 118.2(4) ?
C2 C1 C6 . . 122.1(3) ?
C2 C1 H1A . . 119.0 ?
C6 C1 H1A . . 119.0 ?
C3 C2 C1 . . 118.4(3) ?
C3 C2 H2A . . 120.8 ?
C1 C2 H2A . . 120.8 ?
C2 C3 C4 . . 121.3(3) ?
C2 C3 Cl1 . . 119.6(3) ?
C4 C3 Cl1 . . 119.1(3) ?
C5 C4 C3 . . 119.1(3) ?
C5 C4 H4A . . 120.4 ?
C3 C4 H4A . . 120.4 ?
C4 C5 C6 . . 122.0(3) ?
C4 C5 Cl2 . . 115.8(3) ?
C6 C5 Cl2 . . 122.1(3) ?
C5 C6 C1 . . 117.0(3) ?
C5 C6 C7 . . 127.1(3) ?
C1 C6 C7 . . 115.8(3) ?
N2 C7 O1 . . 112.3(3) ?
N2 C7 C6 . . 127.0(3) ?
O1 C7 C6 . . 120.7(3) ?
N1 C8 N2 . . 113.9(3) ?
N1 C8 C9 . . 122.5(3) ?
N2 C8 C9 . . 123.5(3) ?
C14 C9 C10 . . 119.4(3) ?
C14 C9 C8 . . 119.0(3) ?
C10 C9 C8 . . 121.6(3) ?
C11 C10 C9 . . 121.0(3) ?
C11 C10 H10A . . 119.5 ?
C9 C10 H10A . . 119.5 ?
C10 C11 C12 . . 118.0(3) ?
C10 C11 H11A . . 121.0 ?
C12 C11 H11A . . 121.0 ?
C13 C12 C11 . . 122.3(3) ?
C13 C12 N3 . . 118.4(3) ?
C11 C12 N3 . . 119.3(3) ?
C12 C13 C14 . . 119.2(3) ?
C12 C13 H13A . . 120.4 ?
C14 C13 H13A . . 120.4 ?
C13 C14 C9 . . 120.1(3) ?
C13 C14 H14A . . 120.0 ?
C9 C14 H14A . . 120.0 ?
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 C3 . 1.732(3) ?
Cl2 C5 . 1.739(3) ?
O1 C7 . 1.352(4) ?
O1 N1 . 1.403(4) ?
O2 N3 . 1.207(4) ?
O3 N3 . 1.218(4) ?
N1 C8 . 1.302(5) ?
N2 C7 . 1.289(4) ?
N2 C8 . 1.366(4) ?
N3 C12 . 1.474(5) ?
C1 C2 . 1.383(5) ?
C1 C6 . 1.398(4) ?
C1 H1A . 0.93 ?
C2 C3 . 1.380(5) ?
C2 H2A . 0.93 ?
C3 C4 . 1.381(5) ?
C4 C5 . 1.373(5) ?
C4 H4A . 0.93 ?
C5 C6 . 1.392(4) ?
C6 C7 . 1.458(4) ?
C8 C9 . 1.468(4) ?
C9 C14 . 1.384(4) ?
C9 C10 . 1.390(4) ?
C10 C11 . 1.378(4) ?
C10 H10A . 0.93 ?
C11 C12 . 1.377(5) ?
C11 H11A . 0.93 ?
C12 C13 . 1.371(5) ?
C13 C14 . 1.379(5) ?
C13 H13A . 0.93 ?
C14 H14A . 0.93 ?
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
C13 H13A N1 3_555 0.93 2.54 3.338(5) 144 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 N1 C8 . . . . -0.2(4) ?
C6 C1 C2 C3 . . . . -0.3(5) ?
C1 C2 C3 C4 . . . . 0.4(5) ?
C1 C2 C3 Cl1 . . . . 179.9(3) ?
C2 C3 C4 C5 . . . . -0.6(5) ?
Cl1 C3 C4 C5 . . . . 179.9(3) ?
C3 C4 C5 C6 . . . . 0.7(5) ?
C3 C4 C5 Cl2 . . . . 178.3(3) ?
C4 C5 C6 C1 . . . . -0.6(5) ?
Cl2 C5 C6 C1 . . . . -178.0(3) ?
C4 C5 C6 C7 . . . . 178.5(3) ?
Cl2 C5 C6 C7 . . . . 1.0(5) ?
C2 C1 C6 C5 . . . . 0.4(5) ?
C2 C1 C6 C7 . . . . -178.8(3) ?
C8 N2 C7 O1 . . . . -0.3(4) ?
C8 N2 C7 C6 . . . . 179.1(3) ?
N1 O1 C7 N2 . . . . 0.4(4) ?
N1 O1 C7 C6 . . . . -179.1(3) ?
C5 C6 C7 N2 . . . . -174.0(4) ?
C1 C6 C7 N2 . . . . 5.0(5) ?
C5 C6 C7 O1 . . . . 5.3(5) ?
C1 C6 C7 O1 . . . . -175.6(3) ?
O1 N1 C8 N2 . . . . 0.1(4) ?
O1 N1 C8 C9 . . . . -177.5(3) ?
C7 N2 C8 N1 . . . . 0.2(4) ?
C7 N2 C8 C9 . . . . 177.7(3) ?
N1 C8 C9 C14 . . . . 176.5(4) ?
N2 C8 C9 C14 . . . . -0.8(5) ?
N1 C8 C9 C10 . . . . -2.4(5) ?
N2 C8 C9 C10 . . . . -179.7(3) ?
C14 C9 C10 C11 . . . . 0.0(5) ?
C8 C9 C10 C11 . . . . 178.9(3) ?
C9 C10 C11 C12 . . . . -1.0(5) ?
C10 C11 C12 C13 . . . . 0.6(5) ?
C10 C11 C12 N3 . . . . -178.3(3) ?
O2 N3 C12 C13 . . . . 171.1(4) ?
O3 N3 C12 C13 . . . . -9.9(6) ?
O2 N3 C12 C11 . . . . -9.9(5) ?
O3 N3 C12 C11 . . . . 169.0(4) ?
C11 C12 C13 C14 . . . . 0.8(6) ?
N3 C12 C13 C14 . . . . 179.7(3) ?
C12 C13 C14 C9 . . . . -1.8(6) ?
C10 C9 C14 C13 . . . . 1.4(6) ?
C8 C9 C14 C13 . . . . -177.5(3) ?
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 612744
