#------------------------------------------------------------------------------
#$Date: 2016-02-14 16:26:36 +0200 (Sun, 14 Feb 2016) $
#$Revision: 176435 $
#$URL: svn://www.crystallography.net/cod/cif/2/22/31/2223194.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_2223194
loop_
_publ_author_name
'Akhtar, Tashfeen'
'Khawar Rauf, M.'
'Hameed, Shahid'
'Lu, Xiaoming'
_publ_section_title
;
 5-[1-(3,4-Dichlorophenoxy)ethyl]-1,3,4-oxadiazole-2(3H)-thione
 hemihydrate
;
_journal_coeditor_code           SU2129
_journal_issue                   9
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o2075
_journal_page_last               o2076
_journal_paper_doi               10.1107/S1600536809029894
_journal_volume                  65
_journal_year                    2009
_chemical_formula_iupac          'C10 H8 Cl2 N2 O2 S, 0.5H2 O'
_chemical_formula_moiety         'C10 H8 Cl2 N2 O2 S, 0.5(H2 O)'
_chemical_formula_sum            'C10 H9 Cl2 N2 O2.5 S'
_chemical_formula_weight         300.15
_chemical_name_systematic
;
5-[1-(3,4-Dichlorophenoxy)ethyl]-1,3,4-oxadiazole-2(3H)-
thione hemihydrate
;
_space_group_IT_number           15
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-C 2yc'
_symmetry_space_group_name_H-M   'C 1 2/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                 92.9130(10)
_cell_angle_gamma                90.00
_cell_formula_units_Z            8
_cell_length_a                   11.8725(2)
_cell_length_b                   7.89320(10)
_cell_length_c                   26.6092(4)
_cell_measurement_reflns_used    4427
_cell_measurement_temperature    123(2)
_cell_measurement_theta_max      28.28
_cell_measurement_theta_min      3.10
_cell_volume                     2490.38(6)
_computing_cell_refinement       'SAINT (Bruker, 2007)'
_computing_data_collection       'SMART (Bruker, 2007)'
_computing_data_reduction        'SAINT (Bruker, 2007)'
_computing_molecular_graphics
'ORTEP-3 (Farrugia, 1997) and Mercury (Macrae et al.,  2006)'
_computing_publication_material  'SHELXTL (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      123(2)
_diffrn_measured_fraction_theta_full 0.993
_diffrn_measured_fraction_theta_max 0.993
_diffrn_measurement_device_type  'Bruker SMART CCD area-detector'
_diffrn_measurement_method       'φ and ω'
_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  0.0190
_diffrn_reflns_av_sigmaI/netI    0.0199
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       35
_diffrn_reflns_limit_l_min       -35
_diffrn_reflns_number            10568
_diffrn_reflns_theta_full        28.28
_diffrn_reflns_theta_max         28.28
_diffrn_reflns_theta_min         3.10
_exptl_absorpt_coefficient_mu    0.684
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.601
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             1224
_exptl_crystal_size_max          0.40
_exptl_crystal_size_mid          0.30
_exptl_crystal_size_min          0.25
_refine_diff_density_max         0.222
_refine_diff_density_min         -0.214
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.088
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     162
_refine_ls_number_reflns         3088
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.088
_refine_ls_R_factor_all          0.0352
_refine_ls_R_factor_gt           0.0270
_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)+(0.0399P)²+0.7008P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0744
_refine_ls_wR_factor_ref         0.0778
_reflns_number_gt                2490
_reflns_number_total             3088
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            su2129.cif
_cod_data_source_block           I
_cod_original_sg_symbol_H-M      'C 2/c'
_cod_original_formula_sum        'C10 H9 Cl2 N2 O2.50 S'
_cod_database_code               2223194
_cod_database_fobs_code          2223194
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y, -z+1/2'
'x+1/2, y+1/2, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y, z-1/2'
'-x+1/2, -y+1/2, -z'
'x+1/2, -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_disorder_assembly
_atom_site_disorder_group
O O1 0.25873(7) 0.32348(12) 0.33123(4) 0.0347(2) Uani d . 1 . .
C C1 0.26630(11) 0.47444(17) 0.30643(5) 0.0321(3) Uani d . 1 . .
S S1 0.15653(3) 0.59419(5) 0.290316(15) 0.04313(11) Uani d . 1 . .
N N1 0.37606(9) 0.49544(15) 0.30057(4) 0.0373(3) Uani d . 1 . .
H H1 0.4040 0.5814 0.2857 0.045 Uiso calc R 1 . .
N N2 0.44029(9) 0.36407(16) 0.32095(5) 0.0379(3) Uani d . 1 . .
C C2 0.36727(11) 0.26539(17) 0.33892(5) 0.0330(3) Uani d . 1 . .
C C3 0.38524(12) 0.09920(18) 0.36521(5) 0.0381(3) Uani d . 1 . .
H H3 0.4630 0.0612 0.3616 0.046 Uiso calc R 1 . .
C C4 0.30442(15) -0.0347(2) 0.34486(6) 0.0495(4) Uani d . 1 . .
H H4A 0.3187 -0.1393 0.3625 0.074 Uiso calc R 1 . .
H H4B 0.3148 -0.0510 0.3096 0.074 Uiso calc R 1 . .
H H4C 0.2284 0.0010 0.3495 0.074 Uiso calc R 1 . .
O O2 0.36403(8) 0.11531(14) 0.41765(4) 0.0417(2) Uani d . 1 . .
C C5 0.44340(11) 0.18810(17) 0.45029(5) 0.0351(3) Uani d . 1 . .
C C6 0.54468(11) 0.25923(18) 0.43709(5) 0.0374(3) Uani d . 1 . .
H H6 0.5649 0.2584 0.4038 0.045 Uiso calc R 1 . .
C C7 0.61526(11) 0.33147(19) 0.47429(5) 0.0379(3) Uani d . 1 . .
H H7 0.6830 0.3797 0.4656 0.046 Uiso calc R 1 . .
C C8 0.58683(11) 0.33307(17) 0.52386(5) 0.0354(3) Uani d . 1 . .
Cl Cl1 0.67766(3) 0.42681(5) 0.568937(14) 0.04480(11) Uani d . 1 . .
C C9 0.48523(12) 0.26045(17) 0.53664(5) 0.0360(3) Uani d . 1 . .
Cl Cl2 0.44427(3) 0.26092(6) 0.598122(14) 0.05328(13) Uani d . 1 . .
C C10 0.41405(11) 0.18835(18) 0.50013(5) 0.0380(3) Uani d . 1 . .
H H10 0.3464 0.1399 0.5089 0.046 Uiso calc R 1 . .
O O1W 0.5000 0.75760(19) 0.2500 0.0457(4) Uani d S 1 . .
H H1W 0.5445(15) 0.817(2) 0.2687(7) 0.059 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'
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_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle
_geom_angle_publ_flag
C1 O1 C2 . . 106.18(10) ?
N1 C1 O1 . . 104.71(11) ?
N1 C1 S1 . . 131.59(11) ?
O1 C1 S1 . . 123.69(9) ?
C1 N1 N2 . . 112.63(11) ?
C1 N1 H1 . . 123.7 ?
N2 N1 H1 . . 123.7 ?
C2 N2 N1 . . 103.48(10) ?
N2 C2 O1 . . 112.99(12) ?
N2 C2 C3 . . 128.79(12) ?
O1 C2 C3 . . 118.20(11) ?
O2 C3 C2 . . 110.40(11) ?
O2 C3 C4 . . 105.72(12) ?
C2 C3 C4 . . 111.92(12) ?
O2 C3 H3 . . 109.6 ?
C2 C3 H3 . . 109.6 ?
C4 C3 H3 . . 109.6 ?
C3 C4 H4A . . 109.5 ?
C3 C4 H4B . . 109.5 ?
H4A C4 H4B . . 109.5 ?
C3 C4 H4C . . 109.5 ?
H4A C4 H4C . . 109.5 ?
H4B C4 H4C . . 109.5 ?
C5 O2 C3 . . 120.17(10) ?
O2 C5 C10 . . 114.02(12) ?
O2 C5 C6 . . 125.73(12) ?
C10 C5 C6 . . 120.25(14) ?
C7 C6 C5 . . 119.04(13) ?
C7 C6 H6 . . 120.5 ?
C5 C6 H6 . . 120.5 ?
C8 C7 C6 . . 121.23(13) ?
C8 C7 H7 . . 119.4 ?
C6 C7 H7 . . 119.4 ?
C7 C8 C9 . . 119.15(13) ?
C7 C8 Cl1 . . 119.41(11) ?
C9 C8 Cl1 . . 121.44(10) ?
C10 C9 C8 . . 120.36(12) ?
C10 C9 Cl2 . . 118.41(11) ?
C8 C9 Cl2 . . 121.22(11) ?
C9 C10 C5 . . 119.97(13) ?
C9 C10 H10 . . 120.0 ?
C5 C10 H10 . . 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
O1 C1 . 1.3672(16) ?
O1 C2 . 1.3733(15) ?
C1 N1 . 1.3306(16) ?
C1 S1 . 1.6489(13) ?
N1 N2 . 1.3817(16) ?
N1 H1 . 0.8600 ?
N2 C2 . 1.2763(18) ?
C2 C3 . 1.4967(19) ?
C3 O2 . 1.4363(17) ?
C3 C4 . 1.509(2) ?
C3 H3 . 0.9800 ?
C4 H4A . 0.9600 ?
C4 H4B . 0.9600 ?
C4 H4C . 0.9600 ?
O2 C5 . 1.3745(17) ?
C5 C10 . 1.3882(19) ?
C5 C6 . 1.3884(19) ?
C6 C7 . 1.387(2) ?
C6 H6 . 0.9300 ?
C7 C8 . 1.3783(19) ?
C7 H7 . 0.9300 ?
C8 C9 . 1.3931(19) ?
C8 Cl1 . 1.7371(15) ?
C9 C10 . 1.378(2) ?
C9 Cl2 . 1.7302(14) ?
C10 H10 . 0.9300 ?
O1W H1W . 0.846(17) ?
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
N1 H1 O1W . 0.86 2.06 2.9084(16) 168
O1W H1W S1 3 0.846(17) 2.612(18) 3.3854(13) 152.5(17)
