#------------------------------------------------------------------------------
#$Date: 2017-10-13 12:31:46 +0300 (Fri, 13 Oct 2017) $
#$Revision: 201979 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/23/29/2232942.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_2232942
loop_
_publ_author_name
'Ji, Hao'
'Xu, Xu-Dong'
_publ_section_title
;
 2-Chloro-5-({[5-(4-methoxyphenyl)-1,3,4-oxadiazol-2-yl]sulfanyl}methyl)pyridine
;
_journal_coeditor_code           RZ2672
_journal_issue                   12
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o3490
_journal_paper_doi               10.1107/S1600536811050410
_journal_volume                  67
_journal_year                    2011
_chemical_formula_iupac          'C15 H12 Cl N3 O2 S'
_chemical_formula_moiety         'C15 H12 Cl N3 O2 S'
_chemical_formula_sum            'C15 H12 Cl N3 O2 S'
_chemical_formula_weight         333.80
_chemical_name_systematic
;
2-Chloro-5-({[5-(4-methoxyphenyl)-1,3,4-oxadiazol-2-yl]sulfanyl}methyl)pyridine
;
_space_group_IT_number           61
_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_Hall  '-P 2ac 2ab'
_symmetry_space_group_name_H-M   'P b c a'
_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            8
_cell_length_a                   12.311(2)
_cell_length_b                   8.1229(15)
_cell_length_c                   29.956(6)
_cell_measurement_reflns_used    2256
_cell_measurement_temperature    298(2)
_cell_measurement_theta_max      26
_cell_measurement_theta_min      4.2
_cell_volume                     2995.6(10)
_computing_cell_refinement       'SAINT (Bruker, 1998)'
_computing_data_collection       'SMART (Bruker, 1998)'
_computing_data_reduction        'SAINT (Bruker, 1998)'
_computing_molecular_graphics    'SHELXTL (Sheldrick, 2008)'
_computing_publication_material  SHELXTL
_computing_structure_refinement  'SHELXL97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      298(2)
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device_type
'Bruker SMART APEX area-detector diffractometer'
_diffrn_measurement_method       '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  0.0887
_diffrn_reflns_av_sigmaI/netI    0.0982
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       0
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       35
_diffrn_reflns_limit_l_min       0
_diffrn_reflns_number            5300
_diffrn_reflns_theta_full        25.32
_diffrn_reflns_theta_max         25.32
_diffrn_reflns_theta_min         1.36
_exptl_absorpt_coefficient_mu    0.404
_exptl_absorpt_correction_T_max  0.9796
_exptl_absorpt_correction_T_min  0.8861
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(SADABS; Sheldrick, 1996)'
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.480
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       needle
_exptl_crystal_F_000             1376
_exptl_crystal_size_max          0.30
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.05
_refine_diff_density_max         0.237
_refine_diff_density_min         -0.227
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.969
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     201
_refine_ls_number_reflns         2730
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.969
_refine_ls_R_factor_all          0.1257
_refine_ls_R_factor_gt           0.0599
_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)+(0.0512P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1207
_refine_ls_wR_factor_ref         0.1474
_reflns_number_gt                1514
_reflns_number_total             2730
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            rz2672.cif
_cod_data_source_block           I
_cod_database_code               2232942
_cod_database_fobs_code          2232942
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'-x, y+1/2, -z+1/2'
'x+1/2, -y+1/2, -z'
'-x, -y, -z'
'x-1/2, y, -z-1/2'
'x, -y-1/2, z-1/2'
'-x-1/2, y-1/2, 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_symmetry_multiplicity
C C1 0.5087(4) -0.2986(7) 0.24553(18) 0.0714(16) Uani d . 1 1
H H1A 0.5338 -0.1867 0.2461 0.107 Uiso calc R 1 1
H H1B 0.5102 -0.3387 0.2154 0.107 Uiso calc R 1 1
H H1C 0.5552 -0.3654 0.2638 0.107 Uiso calc R 1 1
C C2 0.3779(4) -0.2211(6) 0.29959(14) 0.0472(11) Uani d . 1 1
C C3 0.4536(3) -0.1655(5) 0.33013(14) 0.0455(11) Uani d . 1 1
H H3 0.5271 -0.1861 0.3256 0.055 Uiso calc R 1 1
C C4 0.4201(3) -0.0794(5) 0.36728(13) 0.0420(11) Uani d . 1 1
H H4 0.4715 -0.0414 0.3876 0.050 Uiso calc R 1 1
C C5 0.3108(3) -0.0486(5) 0.37482(13) 0.0371(10) Uani d . 1 1
C C6 0.2359(3) -0.1103(6) 0.34482(14) 0.0507(12) Uani d . 1 1
H H6 0.1621 -0.0936 0.3498 0.061 Uiso calc R 1 1
C C7 0.2693(4) -0.1962(6) 0.30773(15) 0.0600(14) Uani d . 1 1
H H7 0.2179 -0.2379 0.2880 0.072 Uiso calc R 1 1
C C8 0.2797(3) 0.0489(5) 0.41334(13) 0.0364(10) Uani d . 1 1
C C9 0.1752(3) 0.1674(5) 0.46014(14) 0.0396(11) Uani d . 1 1
C C10 0.1054(4) 0.3455(5) 0.52966(12) 0.0442(11) Uani d . 1 1
H H10A 0.1658 0.4113 0.5190 0.053 Uiso calc R 1 1
H H10B 0.0493 0.4206 0.5397 0.053 Uiso calc R 1 1
C C11 0.1431(3) 0.2446(5) 0.56864(13) 0.0384(10) Uani d . 1 1
C C12 0.2518(3) 0.2350(6) 0.57983(14) 0.0473(11) Uani d . 1 1
H H12 0.3018 0.2869 0.5613 0.057 Uiso calc R 1 1
C C13 0.2170(4) 0.0810(6) 0.64102(14) 0.0454(12) Uani d . 1 1
C C14 0.1079(4) 0.0776(6) 0.63222(15) 0.0518(12) Uani d . 1 1
H H14 0.0604 0.0206 0.6507 0.062 Uiso calc R 1 1
C C15 0.0706(3) 0.1604(6) 0.59533(14) 0.0481(12) Uani d . 1 1
H H15 -0.0030 0.1597 0.5884 0.058 Uiso calc R 1 1
N N1 0.3412(3) 0.1276(4) 0.44087(11) 0.0436(9) Uani d . 1 1
N N2 0.2721(3) 0.2060(5) 0.47184(11) 0.0447(9) Uani d . 1 1
N N3 0.2897(3) 0.1545(5) 0.61608(12) 0.0501(10) Uani d . 1 1
O O1 0.4021(3) -0.3058(5) 0.26198(11) 0.0770(12) Uani d . 1 1
O O2 0.1718(2) 0.0681(3) 0.42357(9) 0.0415(7) Uani d . 1 1
S S 0.05258(9) 0.22470(15) 0.48350(4) 0.0480(3) Uani d . 1 1
Cl Cl1 0.26557(11) -0.01868(18) 0.68838(4) 0.0683(4) 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'
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
O1 C1 H1A 109.5
O1 C1 H1B 109.5
H1A C1 H1B 109.5
O1 C1 H1C 109.5
H1A C1 H1C 109.5
H1B C1 H1C 109.5
O1 C2 C3 124.7(4)
O1 C2 C7 115.9(4)
C3 C2 C7 119.4(4)
C4 C3 C2 120.0(4)
C4 C3 H3 120.0
C2 C3 H3 120.0
C3 C4 C5 120.9(4)
C3 C4 H4 119.6
C5 C4 H4 119.6
C6 C5 C4 118.4(4)
C6 C5 C8 122.6(4)
C4 C5 C8 119.0(4)
C7 C6 C5 120.7(4)
C7 C6 H6 119.7
C5 C6 H6 119.7
C6 C7 C2 120.6(4)
C6 C7 H7 119.7
C2 C7 H7 119.7
N1 C8 O2 111.7(4)
N1 C8 C5 128.6(4)
O2 C8 C5 119.7(4)
N2 C9 O2 113.2(4)
N2 C9 S 129.5(4)
O2 C9 S 117.3(3)
C11 C10 S 114.1(3)
C11 C10 H10A 108.7
S C10 H10A 108.7
C11 C10 H10B 108.7
S C10 H10B 108.7
H10A C10 H10B 107.6
C15 C11 C12 117.2(4)
C15 C11 C10 121.5(4)
C12 C11 C10 121.3(4)
N3 C12 C11 123.9(4)
N3 C12 H12 118.1
C11 C12 H12 118.1
N3 C13 C14 124.7(4)
N3 C13 Cl1 116.2(3)
C14 C13 Cl1 119.0(4)
C13 C14 C15 118.2(4)
C13 C14 H14 120.9
C15 C14 H14 120.9
C14 C15 C11 119.6(4)
C14 C15 H15 120.2
C11 C15 H15 120.2
C8 N1 N2 106.8(3)
C9 N2 N1 105.7(3)
C13 N3 C12 116.3(4)
C2 O1 C1 118.4(4)
C9 O2 C8 102.5(3)
C9 S C10 98.1(2)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
C1 O1 1.404(6)
C1 H1A 0.9600
C1 H1B 0.9600
C1 H1C 0.9600
C2 O1 1.353(5)
C2 C3 1.381(6)
C2 C7 1.375(6)
C3 C4 1.378(5)
C3 H3 0.9300
C4 C5 1.387(5)
C4 H4 0.9300
C5 C6 1.382(5)
C5 C8 1.451(5)
C6 C7 1.375(6)
C6 H6 0.9300
C7 H7 0.9300
C8 N1 1.289(5)
C8 O2 1.372(4)
C9 N2 1.282(5)
C9 O2 1.361(5)
C9 S 1.728(4)
C10 C11 1.500(5)
C10 S 1.816(4)
C10 H10A 0.9700
C10 H10B 0.9700
C11 C15 1.379(5)
C11 C12 1.383(6)
C12 N3 1.350(5)
C12 H12 0.9300
C13 N3 1.310(5)
C13 C14 1.368(6)
C13 Cl1 1.740(4)
C14 C15 1.373(6)
C14 H14 0.9300
C15 H15 0.9300
N1 N2 1.411(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
O1 C2 C3 C4 179.6(4)
C7 C2 C3 C4 -3.0(7)
C2 C3 C4 C5 0.6(7)
C3 C4 C5 C6 1.8(6)
C3 C4 C5 C8 -177.3(4)
C4 C5 C6 C7 -1.8(7)
C8 C5 C6 C7 177.2(4)
C5 C6 C7 C2 -0.6(7)
O1 C2 C7 C6 -179.4(4)
C3 C2 C7 C6 3.0(8)
C6 C5 C8 N1 -171.9(4)
C4 C5 C8 N1 7.2(6)
C6 C5 C8 O2 6.8(6)
C4 C5 C8 O2 -174.1(4)
S C10 C11 C15 -69.6(5)
S C10 C11 C12 111.7(4)
C15 C11 C12 N3 -3.0(7)
C10 C11 C12 N3 175.8(4)
N3 C13 C14 C15 -1.8(8)
Cl1 C13 C14 C15 178.4(4)
C13 C14 C15 C11 -0.4(7)
C12 C11 C15 C14 2.6(7)
C10 C11 C15 C14 -176.1(4)
O2 C8 N1 N2 -0.1(5)
C5 C8 N1 N2 178.7(4)
O2 C9 N2 N1 0.2(5)
S C9 N2 N1 -179.1(3)
C8 N1 N2 C9 0.0(4)
C14 C13 N3 C12 1.6(7)
Cl1 C13 N3 C12 -178.6(3)
C11 C12 N3 C13 0.9(7)
C3 C2 O1 C1 -19.0(7)
C7 C2 O1 C1 163.5(5)
N2 C9 O2 C8 -0.2(4)
S C9 O2 C8 179.1(3)
N1 C8 O2 C9 0.2(4)
C5 C8 O2 C9 -178.7(3)
N2 C9 S C10 -2.2(5)
O2 C9 S C10 178.6(3)
C11 C10 S C9 -79.9(3)
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 26354619
