#------------------------------------------------------------------------------
#$Date: 2017-10-13 09:09:21 +0300 (Fri, 13 Oct 2017) $
#$Revision: 201973 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/20/67/2206785.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_2206785
loop_
_publ_author_name
'Song, Xin-Jian'
'Tan, Xiao-Hong'
'Li, Yao-Hua'
'Zhang, Zheng-Wen'
'Wang, Yan-Gang'
_publ_section_title
;1-[(4-Nitrophenoxy)acetyl]-3-(5-thioxo-4,5-dihydro-1,3,4-thiadiazolin-2-yl)urea
 dimethylformamide solvate
;
_journal_coeditor_code           SG6022
_journal_issue                   9
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o3066
_journal_page_last               o3068
_journal_paper_doi               10.1107/S1600536805026942
_journal_volume                  61
_journal_year                    2005
_chemical_formula_iupac          'C11 H9 N5 O5 S2, C3 H7 N O'
_chemical_formula_moiety         'C11 H9 N5 O5 S2, C3 H7 N O'
_chemical_formula_sum            'C14 H16 N6 O6 S2'
_chemical_formula_weight         428.47
_chemical_melting_point          510
_chemical_name_systematic
;1-[(4-Nitrophenoxy)acetyl]-3-(5-thioxo-4,5-dihydro-1,3,4-thiadiazolin-2-yl)urea
dimethylformamide
 solvate
;
_space_group_IT_number           2
_symmetry_cell_setting           triclinic
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                68.893(2)
_cell_angle_beta                 70.744(2)
_cell_angle_gamma                70.897(2)
_cell_formula_units_Z            2
_cell_length_a                   7.9981(12)
_cell_length_b                   11.3139(16)
_cell_length_c                   12.0232(17)
_cell_measurement_reflns_used    1691
_cell_measurement_temperature    292(2)
_cell_measurement_theta_max      27.50
_cell_measurement_theta_min      2.41
_cell_volume                     931.0(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 0.990
_diffrn_measured_fraction_theta_max 0.990
_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  0.0508
_diffrn_reflns_av_sigmaI/netI    0.0610
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            4982
_diffrn_reflns_theta_full        25.00
_diffrn_reflns_theta_max         25.00
_diffrn_reflns_theta_min         1.87
_diffrn_standards_decay_%        0
_diffrn_standards_interval_count 0
_diffrn_standards_interval_time  0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.332
_exptl_absorpt_correction_T_max  0.9364
_exptl_absorpt_correction_T_min  0.9361
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(SADABS; Sheldrick, 1996)'
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.528
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             444
_exptl_crystal_size_max          0.20
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.20
_refine_diff_density_max         0.268
_refine_diff_density_min         -0.295
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.017
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     255
_refine_ls_number_reflns         3253
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.017
_refine_ls_R_factor_all          0.0671
_refine_ls_R_factor_gt           0.0469
_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)+(0.0673P)²+0.0083P] where P = (Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1096
_refine_ls_wR_factor_ref         0.1306
_reflns_number_gt                2384
_reflns_number_total             3253
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            sg6022.cif
_cod_data_source_block           I
_cod_depositor_comments
;
The following automatic conversions were performed:
'_symmetry_cell_setting' value 'Triclinic' changed to 'triclinic'
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 'Triclinic' changed to 'triclinic'
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_database_code               2206785
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -z'
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
C1 0.0102(4) 1.2362(3) 0.0449(3) 0.0445(7) Uani d . 1 C
C2 0.0080(4) 1.3051(3) 0.1198(3) 0.0491(8) Uani d . 1 C
H2 -0.0275 1.3957 0.0972 0.059 Uiso calc R 1 H
C3 0.0595(4) 1.2367(3) 0.2287(3) 0.0477(7) Uani d . 1 C
H3 0.0576 1.2815 0.2806 0.057 Uiso calc R 1 H
C4 0.1142(4) 1.1016(3) 0.2616(2) 0.0396(7) Uani d . 1 C
C5 0.1162(4) 1.0336(3) 0.1853(3) 0.0466(7) Uani d . 1 C
H5 0.1532 0.9431 0.2067 0.056 Uiso calc R 1 H
C6 0.0622(4) 1.1029(3) 0.0765(3) 0.0494(8) Uani d . 1 C
H6 0.0613 1.0587 0.0249 0.059 Uiso calc R 1 H
C7 0.2258(4) 0.9078(3) 0.4058(3) 0.0464(7) Uani d . 1 C
H7A 0.3233 0.8816 0.3394 0.056 Uiso calc R 1 H
H7B 0.1283 0.8666 0.4209 0.056 Uiso calc R 1 H
C8 0.2957(4) 0.8629(3) 0.5202(3) 0.0412(7) Uani d . 1 C
C9 0.3505(3) 0.9357(3) 0.6723(2) 0.0365(6) Uani d . 1 C
C10 0.4392(4) 0.7698(3) 0.8494(2) 0.0377(6) Uani d . 1 C
C11 0.5082(4) 0.7427(3) 1.0411(3) 0.0413(7) Uani d . 1 C
C12 0.2600(5) 0.4829(3) 0.3610(3) 0.0740(11) Uani d . 1 C
H12A 0.2379 0.4337 0.3190 0.111 Uiso calc R 1 H
H12B 0.3847 0.4894 0.3310 0.111 Uiso calc R 1 H
H12C 0.1810 0.5688 0.3463 0.111 Uiso calc R 1 H
C13 0.2259(6) 0.4867(4) 0.5728(4) 0.0792(12) Uani d . 1 C
H13A 0.1914 0.4367 0.6567 0.119 Uiso calc R 1 H
H13B 0.1411 0.5703 0.5591 0.119 Uiso calc R 1 H
H13C 0.3461 0.4987 0.5560 0.119 Uiso calc R 1 H
C14 0.2038(4) 0.2980(3) 0.5343(3) 0.0528(8) Uani d . 1 C
H14 0.1877 0.2593 0.6185 0.063 Uiso calc R 1 H
N1 -0.0412(4) 1.3055(3) -0.0715(2) 0.0560(7) Uani d . 1 N
N2 0.2994(3) 0.9560(2) 0.56589(19) 0.0387(6) Uani d . 1 N
H2A 0.2666 1.0358 0.5244 0.046 Uiso calc R 1 H
N3 0.3919(3) 0.8093(2) 0.7392(2) 0.0414(6) Uani d . 1 N
H3A 0.3884 0.7505 0.7111 0.050 Uiso calc R 1 H
N4 0.4752(4) 0.6484(2) 0.9077(2) 0.0478(6) Uani d . 1 N
N5 0.5131(3) 0.6363(2) 1.0150(2) 0.0483(6) Uani d . 1 N
H5A 0.5398 0.5604 1.0653 0.058 Uiso calc R 1 H
N6 0.2243(3) 0.4179(2) 0.4918(2) 0.0486(6) Uani d . 1 N
O1 -0.0813(4) 1.4245(3) -0.1013(2) 0.0898(9) Uani d . 1 O
O2 -0.0461(4) 1.2422(3) -0.1337(2) 0.0766(8) Uani d . 1 O
O3 0.1603(3) 1.04469(18) 0.37101(17) 0.0464(5) Uani d . 1 O
O4 0.3427(3) 0.74618(18) 0.56663(19) 0.0531(6) Uani d . 1 O
O5 0.3548(3) 1.02502(19) 0.70263(18) 0.0526(6) Uani d . 1 O
O6 0.2042(4) 0.2330(2) 0.4718(2) 0.0716(7) Uani d . 1 O
S1 0.44859(10) 0.87610(7) 0.92008(7) 0.0417(2) Uani d . 1 S
S2 0.55258(12) 0.74748(9) 1.16429(7) 0.0581(3) 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'
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
C6 C1 C2 121.6(3) ?
C6 C1 N1 118.5(3) ?
C2 C1 N1 119.9(3) ?
C3 C2 C1 118.5(3) ?
C3 C2 H2 120.8 ?
C1 C2 H2 120.8 ?
C2 C3 C4 120.7(3) ?
C2 C3 H3 119.6 ?
C4 C3 H3 119.6 ?
O3 C4 C3 115.6(2) ?
O3 C4 C5 124.2(3) ?
C3 C4 C5 120.1(3) ?
C6 C5 C4 118.9(3) ?
C6 C5 H5 120.6 ?
C4 C5 H5 120.6 ?
C1 C6 C5 120.2(3) ?
C1 C6 H6 119.9 ?
C5 C6 H6 119.9 ?
O3 C7 C8 110.7(2) yes
O3 C7 H7A 109.5 ?
C8 C7 H7A 109.5 ?
O3 C7 H7B 109.5 ?
C8 C7 H7B 109.5 ?
H7A C7 H7B 108.1 ?
O4 C8 N2 124.2(3) yes
O4 C8 C7 118.0(3) ?
N2 C8 C7 117.8(2) yes
O5 C9 N3 123.1(3) ?
O5 C9 N2 121.7(2) yes
N3 C9 N2 115.2(2) yes
N4 C10 N3 120.2(2) ?
N4 C10 S1 115.9(2) yes
N3 C10 S1 123.9(2) ?
N5 C11 S2 126.7(2) ?
N5 C11 S1 107.1(2) yes
S2 C11 S1 126.19(17) yes
N6 C12 H12A 109.5 ?
N6 C12 H12B 109.5 ?
H12A C12 H12B 109.5 ?
N6 C12 H12C 109.5 ?
H12A C12 H12C 109.5 ?
H12B C12 H12C 109.5 ?
N6 C13 H13A 109.5 ?
N6 C13 H13B 109.5 ?
H13A C13 H13B 109.5 ?
N6 C13 H13C 109.5 ?
H13A C13 H13C 109.5 ?
H13B C13 H13C 109.5 ?
O6 C14 N6 125.1(3) ?
O6 C14 H14 117.4 ?
N6 C14 H14 117.4 ?
O1 N1 O2 122.9(3) yes
O1 N1 C1 118.3(3) ?
O2 N1 C1 118.7(3) ?
C8 N2 C9 126.9(2) yes
C8 N2 H2A 116.5 ?
C9 N2 H2A 116.5 ?
C9 N3 C10 123.9(2) ?
C9 N3 H3A 118.1 ?
C10 N3 H3A 118.1 ?
C10 N4 N5 108.3(2) yes
C11 N5 N4 119.7(2) yes
C11 N5 H5A 120.1 ?
N4 N5 H5A 120.1 ?
C14 N6 C12 120.9(3) ?
C14 N6 C13 121.3(3) ?
C12 N6 C13 117.6(3) ?
C4 O3 C7 117.8(2) yes
C10 S1 C11 88.96(13) yes
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_publ_flag
C1 C6 1.368(4) ?
C1 C2 1.380(4) ?
C1 N1 1.457(4) ?
C2 C3 1.379(4) ?
C2 H2 0.9300 ?
C3 C4 1.387(4) ?
C3 H3 0.9300 ?
C4 O3 1.355(3) ?
C4 C5 1.388(4) ?
C5 C6 1.387(4) ?
C5 H5 0.9300 ?
C6 H6 0.9300 ?
C7 O3 1.412(3) ?
C7 C8 1.511(4) ?
C7 H7A 0.9700 ?
C7 H7B 0.9700 ?
C8 O4 1.216(3) yes
C8 N2 1.364(3) yes
C9 O5 1.205(3) yes
C9 N3 1.356(3) yes
C9 N2 1.389(3) yes
C10 N4 1.282(3) yes
C10 N3 1.374(3) yes
C10 S1 1.736(3) yes
C11 N5 1.335(3) yes
C11 S2 1.656(3) yes
C11 S1 1.740(3) yes
C12 N6 1.451(4) ?
C12 H12A 0.9600 ?
C12 H12B 0.9600 ?
C12 H12C 0.9600 ?
C13 N6 1.455(4) ?
C13 H13A 0.9600 ?
C13 H13B 0.9600 ?
C13 H13C 0.9600 ?
C14 O6 1.225(4) ?
C14 N6 1.311(4) ?
C14 H14 0.9300 ?
N1 O1 1.220(3) ?
N1 O2 1.224(3) ?
N2 H2A 0.8600 ?
N3 H3A 0.8600 ?
N4 N5 1.370(3) yes
N5 H5A 0.8600 ?
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
N2 H2A O6 1_565 0.86 2.02 2.852(3) 162
N5 H5A N4 2_667 0.86 2.30 2.991(3) 137
N2 H2A O3 . 0.86 2.23 2.652(3) 110
N3 H3A O4 . 0.86 1.91 2.601(3) 136
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
C6 C1 C2 C3 -0.1(5) ?
N1 C1 C2 C3 -179.2(3) ?
C1 C2 C3 C4 0.7(4) ?
C2 C3 C4 O3 -179.5(3) ?
C2 C3 C4 C5 -0.5(4) ?
O3 C4 C5 C6 178.6(3) ?
C3 C4 C5 C6 -0.3(4) ?
C2 C1 C6 C5 -0.7(5) ?
N1 C1 C6 C5 178.5(3) ?
C4 C5 C6 C1 0.9(5) ?
O3 C7 C8 O4 174.1(2) ?
O3 C7 C8 N2 -4.9(4) ?
C6 C1 N1 O1 -177.5(3) ?
C2 C1 N1 O1 1.7(4) ?
C6 C1 N1 O2 4.0(4) ?
C2 C1 N1 O2 -176.8(3) ?
O4 C8 N2 C9 -2.0(5) yes
C7 C8 N2 C9 176.9(2) ?
O5 C9 N2 C8 177.5(3) yes
N3 C9 N2 C8 -3.5(4) ?
O5 C9 N3 C10 1.5(4) ?
N2 C9 N3 C10 -177.6(2) yes
N4 C10 N3 C9 179.5(3) ?
S1 C10 N3 C9 1.2(4) yes
N3 C10 N4 N5 -178.4(2) ?
S1 C10 N4 N5 0.0(3) ?
S2 C11 N5 N4 -179.0(2) yes
S1 C11 N5 N4 0.4(3) ?
C10 N4 N5 C11 -0.2(4) ?
O6 C14 N6 C12 -3.4(5) ?
O6 C14 N6 C13 -178.6(3) ?
C3 C4 O3 C7 -176.8(2) ?
C5 C4 O3 C7 4.3(4) yes
C8 C7 O3 C4 171.9(2) yes
N4 C10 S1 C11 0.2(2) ?
N3 C10 S1 C11 178.5(2) ?
N5 C11 S1 C10 -0.3(2) ?
S2 C11 S1 C10 179.1(2) yes
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 21128915
