#------------------------------------------------------------------------------
#$Date: 2017-03-17 09:33:33 +0200 (Fri, 17 Mar 2017) $
#$Revision: 194322 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/24/20/2242083.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_2242083
loop_
_publ_author_name
'Kumar, Rajesh'
'Hussain, Shafqat'
'Khan, Khalid M.'
'Perveen, Shahnaz'
'Yousuf, Sammer'
_publ_section_title
;
 Crystal structure and Hirshfeld surface analysis of
 1-(4-chlorophenyl)-2-{[5-(4-chlorophenyl)-1,3,4-oxadiazol-2-yl]sulfanyl}ethanone
;
_journal_coeditor_code           RZ5206
_journal_issue                   4
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              524
_journal_page_last               527
_journal_paper_doi               10.1107/S2056989017003978
_journal_volume                  73
_journal_year                    2017
_chemical_formula_iupac          'C16 H10 Cl2 N2 O2 S'
_chemical_formula_moiety         'C16 H10 Cl2 N2 O2 S'
_chemical_formula_sum            'C16 H10 Cl2 N2 O2 S'
_chemical_formula_weight         365.22
_chemical_name_systematic
1-(4-Chlorophenyl)-2-{[5-(4-chlorophenyl)-1,3,4-oxadiazol-2-yl]sulfanyl}ethanone
_space_group_IT_number           14
_space_group_name_Hall           '-P 2ybc'
_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                 92.0880(10)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   19.1513(7)
_cell_length_b                   11.1589(4)
_cell_length_c                   7.5071(3)
_cell_measurement_reflns_used    3559
_cell_measurement_temperature    273(2)
_cell_measurement_theta_max      27.66
_cell_measurement_theta_min      3.19
_cell_volume                     1603.26(10)
_computing_cell_refinement
;
SAINT (Bruker, 2000)
;
_computing_data_collection
;
SMART (Bruker, 2000)
;
_computing_data_reduction
;
SAINT (Bruker, 2000)
;
_computing_molecular_graphics
;
SHELXTL (Sheldrick, 2008)
;
_computing_publication_material
;
SHELXTL, PARST (Nardelli, 1995) and PLATON (Spek, 2009)
;
_computing_structure_refinement
;
SHELXL97 (Sheldrick, 2008)
;
_computing_structure_solution
;
SHELXS97 (Sheldrick, 2008)
;
_diffrn_ambient_temperature      273(2)
_diffrn_measured_fraction_theta_full 0.947
_diffrn_measured_fraction_theta_max 0.947
_diffrn_measurement_device_type
;
Bruker SMART APEX CCD area-detector
;
_diffrn_measurement_method       'ω scan'
_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  0.0219
_diffrn_reflns_av_sigmaI/netI    0.0225
_diffrn_reflns_limit_h_max       25
_diffrn_reflns_limit_h_min       -25
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       9
_diffrn_reflns_limit_l_min       -9
_diffrn_reflns_number            11526
_diffrn_reflns_theta_full        28.30
_diffrn_reflns_theta_max         28.30
_diffrn_reflns_theta_min         1.06
_exptl_absorpt_coefficient_mu    0.545
_exptl_absorpt_correction_T_max  0.9450
_exptl_absorpt_correction_T_min  0.7839
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
(SADABS; Bruker, 2000)
;
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.513
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             744
_exptl_crystal_size_max          0.47
_exptl_crystal_size_mid          0.39
_exptl_crystal_size_min          0.11
_refine_diff_density_max         0.337
_refine_diff_density_min         -0.262
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.118
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     208
_refine_ls_number_reflns         3762
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.118
_refine_ls_R_factor_all          0.0579
_refine_ls_R_factor_gt           0.0452
_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)+(0.0690P)²+0.2639P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1165
_refine_ls_wR_factor_ref         0.1320
_reflns_number_gt                3058
_reflns_number_total             3762
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            rz5206sup1.cif
_cod_data_source_block           I
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               2242083
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
Cl Cl1 -0.31166(3) 0.71345(7) 0.43607(10) 0.0711(2) Uani d . 1 1
Cl Cl2 0.54160(4) 0.62796(12) -0.30547(16) 0.1258(4) Uani d . 1 1
S S1 0.09911(2) 0.52100(4) 0.14177(7) 0.04411(16) Uani d . 1 1
O O1 -0.01151(8) 0.43467(13) 0.3026(2) 0.0556(4) Uani d . 1 1
O O2 0.21861(7) 0.57741(12) 0.00900(19) 0.0427(3) Uani d . 1 1
N N1 0.14210(9) 0.72473(14) -0.0287(2) 0.0457(4) Uani d . 1 1
N N2 0.20649(9) 0.75906(16) -0.1028(3) 0.0508(4) Uani d . 1 1
C C1 -0.14356(11) 0.50990(18) 0.3877(3) 0.0448(5) Uani d . 1 1
H H1B -0.1303 0.4313 0.4130 0.054 Uiso calc R 1 1
C C2 -0.20957(11) 0.54753(19) 0.4258(3) 0.0494(5) Uani d . 1 1
H H2B -0.2410 0.4953 0.4766 0.059 Uiso calc R 1 1
C C3 -0.22851(10) 0.6646(2) 0.3873(3) 0.0463(5) Uani d . 1 1
C C4 -0.18228(10) 0.74359(19) 0.3131(3) 0.0471(5) Uani d . 1 1
H H4A -0.1958 0.8222 0.2889 0.057 Uiso calc R 1 1
C C5 -0.11620(10) 0.70548(17) 0.2752(3) 0.0428(4) Uani d . 1 1
H H5A -0.0849 0.7583 0.2250 0.051 Uiso calc R 1 1
C C6 -0.09600(9) 0.58753(16) 0.3118(3) 0.0375(4) Uani d . 1 1
C C7 -0.02636(10) 0.53891(16) 0.2705(3) 0.0394(4) Uani d . 1 1
C C8 0.02691(9) 0.61879(16) 0.1858(3) 0.0410(4) Uani d . 1 1
H H8A 0.0415 0.6828 0.2663 0.049 Uiso calc R 1 1
H H8B 0.0079 0.6537 0.0761 0.049 Uiso calc R 1 1
C C9 0.15279(9) 0.61954(16) 0.0337(3) 0.0385(4) Uani d . 1 1
C C10 0.24856(10) 0.67088(18) -0.0775(3) 0.0419(4) Uani d . 1 1
C C11 0.32086(10) 0.6589(2) -0.1300(3) 0.0466(5) Uani d . 1 1
C C12 0.35671(13) 0.7597(2) -0.1857(3) 0.0611(6) Uani d . 1 1
H H12A 0.3347 0.8340 -0.1876 0.073 Uiso calc R 1 1
C C13 0.42443(14) 0.7499(3) -0.2380(4) 0.0743(8) Uani d . 1 1
H H13A 0.4485 0.8174 -0.2747 0.089 Uiso calc R 1 1
C C14 0.45624(12) 0.6400(3) -0.2356(4) 0.0760(8) Uani d . 1 1
C C15 0.42210(13) 0.5394(3) -0.1805(5) 0.0819(9) Uani d . 1 1
H H15A 0.4444 0.4654 -0.1793 0.098 Uiso calc R 1 1
C C16 0.35398(12) 0.5494(2) -0.1265(4) 0.0643(7) Uani d . 1 1
H H16A 0.3305 0.4818 -0.0877 0.077 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'
S S 0.1246 0.1234 '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
C9 S1 C8 100.05(9)
C9 O2 C10 101.97(14)
C9 N1 N2 105.12(15)
C10 N2 N1 106.51(16)
C2 C1 C6 121.04(18)
C2 C1 H1B 119.5
C6 C1 H1B 119.5
C1 C2 C3 118.81(18)
C1 C2 H2B 120.6
C3 C2 H2B 120.6
C4 C3 C2 121.32(18)
C4 C3 Cl1 119.47(17)
C2 C3 Cl1 119.20(16)
C5 C4 C3 119.66(19)
C5 C4 H4A 120.2
C3 C4 H4A 120.2
C4 C5 C6 120.09(18)
C4 C5 H5A 120.0
C6 C5 H5A 120.0
C1 C6 C5 119.08(17)
C1 C6 C7 117.65(17)
C5 C6 C7 123.26(17)
O1 C7 C6 120.85(17)
O1 C7 C8 119.29(17)
C6 C7 C8 119.85(16)
C7 C8 S1 104.72(12)
C7 C8 H8A 110.8
S1 C8 H8A 110.8
C7 C8 H8B 110.8
S1 C8 H8B 110.8
H8A C8 H8B 108.9
N1 C9 O2 113.80(16)
N1 C9 S1 131.81(14)
O2 C9 S1 114.39(13)
N2 C10 O2 112.59(17)
N2 C10 C11 128.91(19)
O2 C10 C11 118.50(17)
C16 C11 C12 119.5(2)
C16 C11 C10 121.17(19)
C12 C11 C10 119.4(2)
C13 C12 C11 120.2(3)
C13 C12 H12A 119.9
C11 C12 H12A 119.9
C14 C13 C12 119.5(2)
C14 C13 H13A 120.3
C12 C13 H13A 120.3
C13 C14 C15 121.4(2)
C13 C14 Cl2 119.2(2)
C15 C14 Cl2 119.4(2)
C14 C15 C16 119.2(3)
C14 C15 H15A 120.4
C16 C15 H15A 120.4
C11 C16 C15 120.3(2)
C11 C16 H16A 119.9
C15 C16 H16A 119.9
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
Cl1 C3 1.735(2)
Cl2 C14 1.740(2)
S1 C9 1.7279(19)
S1 C8 1.8014(18)
O1 C7 1.219(2)
O2 C9 1.364(2)
O2 C10 1.366(2)
N1 C9 1.277(2)
N1 N2 1.424(2)
N2 C10 1.281(3)
C1 C2 1.372(3)
C1 C6 1.394(3)
C1 H1B 0.9300
C2 C3 1.384(3)
C2 H2B 0.9300
C3 C4 1.381(3)
C4 C5 1.375(3)
C4 H4A 0.9300
C5 C6 1.396(3)
C5 H5A 0.9300
C6 C7 1.483(2)
C7 C8 1.512(2)
C8 H8A 0.9700
C8 H8B 0.9700
C10 C11 1.459(3)
C11 C16 1.376(3)
C11 C12 1.390(3)
C12 C13 1.373(3)
C12 H12A 0.9300
C13 C14 1.369(4)
C13 H13A 0.9300
C14 C15 1.370(4)
C15 C16 1.385(3)
C15 H15A 0.9300
C16 H16A 0.9300
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
C1 H1B N1 2_545 0.93 2.48 3.353(3) 157.0 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
C9 N1 N2 C10 0.2(2)
C6 C1 C2 C3 0.1(3)
C1 C2 C3 C4 -0.5(3)
C1 C2 C3 Cl1 -179.61(17)
C2 C3 C4 C5 0.5(3)
Cl1 C3 C4 C5 179.62(16)
C3 C4 C5 C6 -0.1(3)
C2 C1 C6 C5 0.3(3)
C2 C1 C6 C7 -178.44(19)
C4 C5 C6 C1 -0.3(3)
C4 C5 C6 C7 178.38(18)
C1 C6 C7 O1 -0.2(3)
C5 C6 C7 O1 -178.9(2)
C1 C6 C7 C8 179.18(17)
C5 C6 C7 C8 0.5(3)
O1 C7 C8 S1 4.4(2)
C6 C7 C8 S1 -174.98(14)
C9 S1 C8 C7 176.28(13)
N2 N1 C9 O2 -0.2(2)
N2 N1 C9 S1 -179.78(16)
C10 O2 C9 N1 0.2(2)
C10 O2 C9 S1 179.80(13)
C8 S1 C9 N1 -11.3(2)
C8 S1 C9 O2 169.15(14)
N1 N2 C10 O2 -0.1(2)
N1 N2 C10 C11 179.0(2)
C9 O2 C10 N2 0.0(2)
C9 O2 C10 C11 -179.28(17)
N2 C10 C11 C16 -166.0(2)
O2 C10 C11 C16 13.1(3)
N2 C10 C11 C12 13.5(4)
O2 C10 C11 C12 -167.4(2)
C16 C11 C12 C13 0.5(4)
C10 C11 C12 C13 -179.1(2)
C11 C12 C13 C14 0.3(4)
C12 C13 C14 C15 -0.6(5)
C12 C13 C14 Cl2 179.0(2)
C13 C14 C15 C16 0.1(5)
Cl2 C14 C15 C16 -179.4(2)
C12 C11 C16 C15 -0.9(4)
C10 C11 C16 C15 178.6(2)
C14 C15 C16 C11 0.6(5)

_cod_database_fobs_code 2242083
