#------------------------------------------------------------------------------
#$Date: 2017-10-13 09:09:21 +0300 (Fri, 13 Oct 2017) $
#$Revision: 201973 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/20/63/2206322.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_2206322
loop_
_publ_author_name
'Song, Xin-Jian'
'Shi, Bo-An'
'Wang, Yan-Gang'
'Liu, Hong-Xia'
'Wang, Yan'
_publ_section_title
2-(2,4-Dichlorophenoxy)-N-[5-(3-pyridyl)-1,3,4-thiadiazol-2-yl]acetamide
_journal_issue                   7
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o2254
_journal_page_last               o2255
_journal_paper_doi               10.1107/S1600536805019343
_journal_volume                  61
_journal_year                    2005
_chemical_formula_iupac          'C15 H10 Cl2 N4 O2 S'
_chemical_formula_moiety         'C15 H10 Cl2 N4 O2 S'
_chemical_formula_sum            'C15 H10 Cl2 N4 O2 S'
_chemical_formula_weight         381.23
_chemical_melting_point          528
_chemical_name_systematic
;
2-(2,4-Dichlorophenoxy)-N-[5-(3-pyridyl)-1,3,4-thiadiazol-2-yl]acetamide
;
_space_group_IT_number           14
_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           SHELXL97
_cell_angle_alpha                90.00
_cell_angle_beta                 92.811(2)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   7.6550(7)
_cell_length_b                   9.0221(8)
_cell_length_c                   22.927(2)
_cell_measurement_reflns_used    2934
_cell_measurement_temperature    292(2)
_cell_measurement_theta_max      27.67
_cell_measurement_theta_min      2.43
_cell_volume                     1581.5(2)
_computing_cell_refinement       'SAINT (Bruker, 2001)'
_computing_data_collection       'SMART (Bruker, 2001)'
_computing_data_reduction        SAINT
_computing_molecular_graphics    'SHELXTL (Sheldrick, 2001)'
_computing_publication_material  SHELXTL
_computing_structure_refinement  'SHELXL97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 1997)'
_diffrn_ambient_temperature      292(2)
_diffrn_measured_fraction_theta_full 0.996
_diffrn_measured_fraction_theta_max 0.996
_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  0.0237
_diffrn_reflns_av_sigmaI/netI    0.0321
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       28
_diffrn_reflns_limit_l_min       -28
_diffrn_reflns_number            8360
_diffrn_reflns_theta_full        26.00
_diffrn_reflns_theta_max         26.00
_diffrn_reflns_theta_min         1.78
_diffrn_standards_decay_%        0
_diffrn_standards_interval_count 0
_diffrn_standards_interval_time  0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.559
_exptl_absorpt_correction_T_max  0.8964
_exptl_absorpt_correction_T_min  0.8502
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(SADABS; Sheldrick, 1996)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.601
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             776
_exptl_crystal_size_max          0.30
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.20
_refine_diff_density_max         0.386
_refine_diff_density_min         -0.208
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.078
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     217
_refine_ls_number_reflns         3100
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.078
_refine_ls_R_factor_all          0.0503
_refine_ls_R_factor_gt           0.0419
_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)+(0.0684P)²+0.38P] where P = (Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1076
_refine_ls_wR_factor_ref         0.1216
_reflns_number_gt                2641
_reflns_number_total             3100
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            ww6406.cif
_cod_data_source_block           I
_cod_depositor_comments
;
The following automatic conversions were performed:
'_symmetry_cell_setting' value 'Monoclinic' changed to 'monoclinic'
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 

The following automatic conversions were performed:

'_symmetry_cell_setting' value 'Monoclinic' changed to 'monoclinic'
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_values 1715 2011-07-08 13:25:40Z adriana 
;
_cod_original_cell_volume        1581.6(2)
_cod_original_sg_symbol_H-M      'P 21 /c'
_cod_database_code               2206322
_cod_database_fobs_code          2206322
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_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_type_symbol
C6 0.8000(3) 0.7468(2) 0.12476(9) 0.0307(5) Uani d . 1 C
C1 0.8454(3) 0.8435(3) 0.08093(9) 0.0357(5) Uani d . 1 C
C2 0.9129(3) 0.9821(3) 0.09370(10) 0.0390(5) Uani d . 1 C
H2 0.9429 1.0457 0.0639 0.047 Uiso calc R 1 H
C3 0.9354(3) 1.0252(2) 0.15107(10) 0.0347(5) Uani d . 1 C
C4 0.8882(3) 0.9337(3) 0.19528(11) 0.0398(6) Uani d . 1 C
H4 0.9016 0.9647 0.2339 0.048 Uiso calc R 1 H
C5 0.8202(3) 0.7947(3) 0.18206(10) 0.0383(6) Uani d . 1 C
H5 0.7877 0.7328 0.2121 0.046 Uiso calc R 1 H
C7 0.6985(3) 0.5153(2) 0.15412(10) 0.0377(5) Uani d . 1 C
H7A 0.6156 0.5634 0.1786 0.045 Uiso calc R 1 H
H7B 0.8044 0.4960 0.1779 0.045 Uiso calc R 1 H
C8 0.6227(3) 0.3705(2) 0.13181(10) 0.0346(5) Uani d . 1 C
C9 0.4995(3) 0.1486(2) 0.17362(9) 0.0297(5) Uani d . 1 C
C10 0.3824(3) -0.0900(2) 0.15232(9) 0.0307(5) Uani d . 1 C
C11 0.3137(3) -0.2302(2) 0.12851(10) 0.0327(5) Uani d . 1 C
C15 0.2317(3) -0.3286(3) 0.16523(10) 0.0388(5) Uani d . 1 C
H15 0.2238 -0.3020 0.2042 0.047 Uiso calc R 1 H
C14 0.1757(4) -0.4917(3) 0.09168(12) 0.0572(8) Uani d . 1 C
H14 0.1280 -0.5811 0.0785 0.069 Uiso calc R 1 H
C13 0.2532(4) -0.4032(3) 0.05207(12) 0.0603(8) Uani d . 1 C
H13 0.2586 -0.4324 0.0133 0.072 Uiso calc R 1 H
C12 0.3231(4) -0.2696(3) 0.07075(11) 0.0484(7) Uani d . 1 C
H12 0.3760 -0.2069 0.0447 0.058 Uiso calc R 1 H
Cl1 0.81031(12) 0.79051(8) 0.00883(3) 0.0654(3) Uani d . 1 Cl
Cl2 1.02256(9) 1.19985(7) 0.16702(3) 0.0489(2) Uani d . 1 Cl
N1 0.5670(3) 0.2889(2) 0.17763(8) 0.0346(4) Uani d . 1 N
H1 0.5750 0.3290 0.2117 0.041 Uiso calc R 1 H
N2 0.4626(3) 0.0771(2) 0.22056(8) 0.0358(5) Uani d . 1 N
N3 0.3953(3) -0.0613(2) 0.20804(8) 0.0352(4) Uani d . 1 N
N4 0.1641(3) -0.4580(2) 0.14819(9) 0.0493(6) Uani d . 1 N
O1 0.7374(2) 0.61078(17) 0.10759(6) 0.0379(4) Uani d . 1 O
O2 0.6136(3) 0.3275(2) 0.08191(7) 0.0505(5) Uani d . 1 O
S1 0.45450(8) 0.05412(6) 0.10930(2) 0.03408(18) Uani d . 1 S
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
_geom_angle_publ_flag
O1 C6 C5 125.05(19) ?
O1 C6 C1 116.87(19) ?
C5 C6 C1 118.1(2) ?
C2 C1 C6 121.4(2) ?
C2 C1 Cl1 119.50(18) ?
C6 C1 Cl1 119.09(18) ?
C3 C2 C1 119.2(2) ?
C3 C2 H2 120.4 ?
C1 C2 H2 120.4 ?
C4 C3 C2 120.9(2) ?
C4 C3 Cl2 120.10(18) ?
C2 C3 Cl2 119.01(18) ?
C3 C4 C5 119.6(2) ?
C3 C4 H4 120.2 ?
C5 C4 H4 120.2 ?
C6 C5 C4 120.9(2) ?
C6 C5 H5 119.6 ?
C4 C5 H5 119.6 ?
O1 C7 C8 111.30(18) ?
O1 C7 H7A 109.4 ?
C8 C7 H7A 109.4 ?
O1 C7 H7B 109.4 ?
C8 C7 H7B 109.4 ?
H7A C7 H7B 108.0 ?
O2 C8 N1 123.3(2) yes
O2 C8 C7 127.1(2) yes
N1 C8 C7 109.58(18) yes
N2 C9 N1 120.06(19) ?
N2 C9 S1 114.90(17) ?
N1 C9 S1 125.04(16) ?
N3 C10 C11 123.07(19) yes
N3 C10 S1 113.39(16) ?
C11 C10 S1 123.54(16) ?
C12 C11 C15 117.6(2) ?
C12 C11 C10 123.1(2) ?
C15 C11 C10 119.3(2) ?
N4 C15 C11 124.3(2) ?
N4 C15 H15 117.9 ?
C11 C15 H15 117.9 ?
N4 C14 C13 124.3(3) ?
N4 C14 H14 117.9 ?
C13 C14 H14 117.9 ?
C14 C13 C12 118.6(3) ?
C14 C13 H13 120.7 ?
C12 C13 H13 120.7 ?
C11 C12 C13 119.1(2) ?
C11 C12 H12 120.4 ?
C13 C12 H12 120.4 ?
C8 N1 C9 125.25(19) yes
C8 N1 H1 117.4 ?
C9 N1 H1 117.4 ?
C9 N2 N3 111.89(18) ?
C10 N3 N2 113.24(18) ?
C15 N4 C14 116.1(2) ?
C6 O1 C7 114.39(17) yes
C9 S1 C10 86.58(10) ?
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_publ_flag
C6 O1 1.368(3) yes
C6 C5 1.385(3) ?
C6 C1 1.387(3) ?
C1 C2 1.380(3) ?
C1 Cl1 1.729(2) ?
C2 C3 1.374(3) ?
C2 H2 0.9300 ?
C3 C4 1.369(3) ?
C3 Cl2 1.743(2) ?
C4 C5 1.386(3) ?
C4 H4 0.9300 ?
C5 H5 0.9300 ?
C7 O1 1.414(3) ?
C7 C8 1.509(3) yes
C7 H7A 0.9700 ?
C7 H7B 0.9700 ?
C8 O2 1.207(3) yes
C8 N1 1.368(3) yes
C9 N2 1.298(3) yes
C9 N1 1.368(3) yes
C9 S1 1.724(2) ?
C10 N3 1.302(3) yes
C10 C11 1.465(3) yes
C10 S1 1.738(2) ?
C11 C12 1.377(3) ?
C11 C15 1.394(3) ?
C15 N4 1.328(3) yes
C15 H15 0.9300 ?
C14 N4 1.338(3) yes
C14 C13 1.366(4) ?
C14 H14 0.9300 ?
C13 C12 1.378(4) ?
C13 H13 0.9300 ?
C12 H12 0.9300 ?
N1 H1 0.8600 ?
N2 N3 1.376(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
C14 H14 Cl1 3_655 0.93 2.81 3.552(3) 138
C7 H7A N2 2_655 0.97 2.42 3.230(3) 141
N1 H1 N3 2_655 0.86 2.09 2.951(3) 176
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
_geom_torsion_publ_flag
O1 C6 C1 C2 -178.8(2) ?
C5 C6 C1 C2 1.6(4) ?
O1 C6 C1 Cl1 3.2(3) ?
C5 C6 C1 Cl1 -176.47(19) ?
C6 C1 C2 C3 -0.1(4) ?
Cl1 C1 C2 C3 178.00(19) ?
C1 C2 C3 C4 -1.4(4) ?
C1 C2 C3 Cl2 179.44(18) ?
C2 C3 C4 C5 1.4(4) ?
Cl2 C3 C4 C5 -179.54(18) ?
O1 C6 C5 C4 178.7(2) ?
C1 C6 C5 C4 -1.7(4) ?
C3 C4 C5 C6 0.3(4) ?
O1 C7 C8 O2 9.0(4) yes
O1 C7 C8 N1 -172.60(19) yes
N3 C10 C11 C12 -170.3(2) ?
S1 C10 C11 C12 9.7(3) ?
N3 C10 C11 C15 10.9(3) ?
S1 C10 C11 C15 -169.10(18) yes
C12 C11 C15 N4 0.7(4) ?
C10 C11 C15 N4 179.6(2) ?
N4 C14 C13 C12 -0.6(5) ?
C15 C11 C12 C13 -0.5(4) ?
C10 C11 C12 C13 -179.3(3) ?
C14 C13 C12 C11 0.4(5) ?
O2 C8 N1 C9 2.0(4) yes
C7 C8 N1 C9 -176.5(2) ?
N2 C9 N1 C8 174.9(2) ?
S1 C9 N1 C8 -5.9(3) yes
N1 C9 N2 N3 179.63(19) ?
S1 C9 N2 N3 0.4(3) ?
C11 C10 N3 N2 -179.75(19) ?
S1 C10 N3 N2 0.3(2) ?
C9 N2 N3 C10 -0.4(3) ?
C11 C15 N4 C14 -0.9(4) ?
C13 C14 N4 C15 0.8(5) ?
C5 C6 O1 C7 -2.3(3) yes
C1 C6 O1 C7 178.1(2) ?
C8 C7 O1 C6 177.43(19) ?
N2 C9 S1 C10 -0.19(18) ?
N1 C9 S1 C10 -179.4(2) ?
N3 C10 S1 C9 -0.05(18) ?
C11 C10 S1 C9 179.97(19) ?
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 3345247
