#------------------------------------------------------------------------------
#$Date: 2017-10-13 11:03:29 +0300 (Fri, 13 Oct 2017) $
#$Revision: 201974 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/21/01/2210139.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_2210139
loop_
_publ_author_name
'Qian-Jin Li'
'Chun-Long Yang'
'Xue-Qun Xie'
'Jin-Xiang Luo'
_publ_section_title
;
 N-(2,4-Dichlorophenoxyacetyl)-N'-(4-nitrophenyl)thiourea
;
_journal_coeditor_code           BX2018
_journal_issue                   9
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o4102
_journal_page_last               o4103
_journal_paper_doi               10.1107/S1600536806033010
_journal_volume                  62
_journal_year                    2006
_chemical_formula_iupac          'C15 H11 Cl2 N3 O4 S'
_chemical_formula_moiety         'C15 H11 Cl2 N3 O4 S'
_chemical_formula_sum            'C15 H11 Cl2 N3 O4 S'
_chemical_formula_weight         400.23
_chemical_name_systematic
;
N-(2,4-dichlorophenoxyacetyl)-N'-(4-nitrophenyl)thiourea
;
_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
_cell_angle_alpha                90.00
_cell_angle_beta                 109.18(3)
_cell_angle_gamma                90.00
_cell_formula_units_Z            8
_cell_length_a                   23.315(5)
_cell_length_b                   8.3190(17)
_cell_length_c                   18.452(4)
_cell_measurement_reflns_used    25
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      13
_cell_measurement_theta_min      10
_cell_volume                     3380.2(14)
_computing_cell_refinement       'CAD-4 Software'
_computing_data_collection       'CAD-4 Software (Enraf--Nonius, 1989)'
_computing_data_reduction        'XCAD4 (Harms & Wocadlo, 1995)'
_computing_molecular_graphics    'SHELXTL (Bruker, 1998)'
_computing_publication_material  SHELXTL
_computing_structure_refinement  'SHELXL97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 1997)'
_diffrn_ambient_temperature      293(2)
_diffrn_measured_fraction_theta_full 0.996
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measurement_device_type  'Enraf--Nonius CAD-4'
_diffrn_measurement_method       ω/2θ
_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  0.0403
_diffrn_reflns_av_sigmaI/netI    0.0552
_diffrn_reflns_limit_h_max       28
_diffrn_reflns_limit_h_min       0
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       0
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_number            3400
_diffrn_reflns_theta_full        26.02
_diffrn_reflns_theta_max         26.02
_diffrn_reflns_theta_min         1.85
_diffrn_standards_decay_%        0
_diffrn_standards_interval_count 200
_diffrn_standards_interval_time  2
_diffrn_standards_number         3
_exptl_absorpt_coefficient_mu    0.534
_exptl_absorpt_correction_T_max  0.9007
_exptl_absorpt_correction_T_min  0.8148
_exptl_absorpt_correction_type   psi-scan
_exptl_absorpt_process_details   '(XCAD4; Harms & Wocadlo, 1995)'
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.573
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             1632
_exptl_crystal_size_max          0.40
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.20
_refine_diff_density_max         0.347
_refine_diff_density_min         -0.319
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.083
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     226
_refine_ls_number_reflns         3316
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.083
_refine_ls_R_factor_all          0.1183
_refine_ls_R_factor_gt           0.0639
_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)+(0.065P)²+3.2P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1386
_refine_ls_wR_factor_ref         0.1701
_reflns_number_gt                1943
_reflns_number_total             3316
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            bx2018.cif
_cod_data_source_block           I
_cod_original_sg_symbol_Hall     -c2yc
_cod_original_sg_symbol_H-M      'C 2/c'
_cod_database_code               2210139
_cod_database_fobs_code          2210139
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
Cl Cl1 0.30929(7) -0.16682(16) 0.13860(10) 0.0885(5) Uani d . 1
Cl Cl2 0.50527(5) 0.18519(16) 0.14942(7) 0.0669(4) Uani d . 1
S S 0.63448(6) 0.47539(16) 0.03631(7) 0.0687(4) Uani d . 1
O O1 0.45816(13) 0.1708(4) -0.01329(17) 0.0625(9) Uani d . 1
O O2 0.48267(14) 0.3136(4) -0.17918(18) 0.0686(9) Uani d . 1
O O3 0.72048(17) 0.8842(5) -0.2984(2) 0.0862(12) Uani d . 1
O O4 0.79429(17) 0.8514(5) -0.1942(2) 0.0872(12) Uani d . 1
N N1 0.53525(16) 0.3406(4) -0.05133(19) 0.0509(9) Uani d . 1
H H1A 0.5331 0.3140 -0.0073 0.061 Uiso calc R 1
N N2 0.58891(15) 0.4661(4) -0.11901(18) 0.0493(9) Uani d . 1
H H2A 0.5602 0.4244 -0.1563 0.059 Uiso calc R 1
N N3 0.74164(19) 0.8327(5) -0.2334(2) 0.0626(10) Uani d . 1
C C1 0.3522(2) -0.0664(5) 0.0917(3) 0.0572(12) Uani d . 1
C C2 0.3332(2) -0.0604(5) 0.0134(3) 0.0616(13) Uani d . 1
H H2B 0.2966 -0.1085 -0.0148 0.074 Uiso calc R 1
C C3 0.3675(2) 0.0160(5) -0.0240(3) 0.0573(11) Uani d . 1
H H3A 0.3550 0.0157 -0.0773 0.069 Uiso calc R 1
C C4 0.42072(19) 0.0937(5) 0.0174(2) 0.0485(10) Uani d . 1
C C5 0.43892(18) 0.0884(5) 0.0971(2) 0.0488(10) Uani d . 1
C C6 0.4053(2) 0.0077(5) 0.1344(3) 0.0554(11) Uani d . 1
H H6A 0.4182 0.0033 0.1877 0.067 Uiso calc R 1
C C7 0.4400(2) 0.1938(6) -0.0935(2) 0.0570(12) Uani d . 1
H H7A 0.4017 0.2513 -0.1110 0.068 Uiso calc R 1
H H7B 0.4345 0.0906 -0.1194 0.068 Uiso calc R 1
C C8 0.4884(2) 0.2891(5) -0.1123(3) 0.0517(11) Uani d . 1
C C9 0.5865(2) 0.4302(5) -0.0488(2) 0.0512(11) Uani d . 1
C C10 0.63035(19) 0.5604(5) -0.1419(2) 0.0460(10) Uani d . 1
C C11 0.61426(19) 0.5855(5) -0.2200(2) 0.0536(11) Uani d . 1
H H11A 0.5784 0.5412 -0.2525 0.064 Uiso calc R 1
C C12 0.65013(19) 0.6741(5) -0.2502(2) 0.0528(11) Uani d . 1
H H12A 0.6390 0.6906 -0.3029 0.063 Uiso calc R 1
C C13 0.70294(18) 0.7385(5) -0.2014(2) 0.0445(10) Uani d . 1
C C14 0.7206(2) 0.7137(5) -0.1237(2) 0.0550(11) Uani d . 1
H H14A 0.7567 0.7572 -0.0915 0.066 Uiso calc R 1
C C15 0.68373(19) 0.6229(5) -0.0938(2) 0.0549(11) Uani d . 1
H H15A 0.6952 0.6044 -0.0412 0.066 Uiso calc R 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
_geom_angle_publ_flag
C4 O1 C7 119.5(3) yes
C8 N1 C9 130.2(4) yes
C8 N1 H1A 114.9 ?
C9 N1 H1A 114.9 ?
C9 N2 C10 131.2(4) yes
C9 N2 H2A 114.4 ?
C10 N2 H2A 114.4 ?
O4 N3 O3 123.2(4) ?
O4 N3 C13 117.8(4) ?
O3 N3 C13 119.0(4) ?
C2 C1 C6 120.6(4) ?
C2 C1 Cl1 120.3(4) ?
C6 C1 Cl1 119.1(4) ?
C1 C2 C3 120.5(4) ?
C1 C2 H2B 119.7 ?
C3 C2 H2B 119.7 ?
C2 C3 C4 120.3(4) ?
C2 C3 H3A 119.9 ?
C4 C3 H3A 119.9 ?
O1 C4 C3 125.2(4) ?
O1 C4 C5 116.4(4) ?
C3 C4 C5 118.3(4) ?
C6 C5 C4 121.2(4) ?
C6 C5 Cl2 120.0(4) ?
C4 C5 Cl2 118.8(3) ?
C1 C6 C5 119.1(4) ?
C1 C6 H6A 120.5 ?
C5 C6 H6A 120.5 ?
O1 C7 C8 108.8(4) yes
O1 C7 H7A 109.9 ?
C8 C7 H7A 109.9 ?
O1 C7 H7B 109.9 ?
C8 C7 H7B 109.9 ?
H7A C7 H7B 108.3 ?
O2 C8 N1 125.4(4) yes
O2 C8 C7 118.7(4) yes
N1 C8 C7 115.8(4) yes
N2 C9 N1 113.0(4) yes
N2 C9 S 129.5(3) yes
N1 C9 S 117.5(3) yes
C15 C10 C11 119.7(4) ?
C15 C10 N2 125.6(4) yes
C11 C10 N2 114.7(4) ?
C12 C11 C10 121.0(4) ?
C12 C11 H11A 119.5 ?
C10 C11 H11A 119.5 ?
C11 C12 C13 118.7(4) ?
C11 C12 H12A 120.6 ?
C13 C12 H12A 120.6 ?
C14 C13 C12 121.6(4) ?
C14 C13 N3 119.4(4) ?
C12 C13 N3 119.0(4) ?
C13 C14 C15 119.0(4) ?
C13 C14 H14A 120.5 ?
C15 C14 H14A 120.5 ?
C10 C15 C14 119.9(4) ?
C10 C15 H15A 120.1 ?
C14 C15 H15A 120.1 ?
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_publ_flag
Cl1 C1 1.738(5) ?
Cl2 C5 1.730(4) ?
S C9 1.644(5) yes
O1 C4 1.349(5) yes
O1 C7 1.413(5) yes
O2 C8 1.215(5) ?
O3 N3 1.215(5) ?
O4 N3 1.213(5) ?
N1 C8 1.355(5) yes
N1 C9 1.395(5) yes
N1 H1A 0.8600 ?
N2 C9 1.350(5) yes
N2 C10 1.412(5) yes
N2 H2A 0.8600 ?
N3 C13 1.459(5) ?
C1 C2 1.365(6) ?
C1 C6 1.375(6) ?
C2 C3 1.372(6) ?
C2 H2B 0.9300 ?
C3 C4 1.385(6) ?
C3 H3A 0.9300 ?
C4 C5 1.391(6) ?
C5 C6 1.376(6) ?
C6 H6A 0.9300 ?
C7 C8 1.509(6) yes
C7 H7A 0.9700 ?
C7 H7B 0.9700 ?
C10 C15 1.371(6) yes
C10 C11 1.381(5) yes
C11 C12 1.364(6) ?
C11 H11A 0.9300 ?
C12 C13 1.373(6) ?
C12 H12A 0.9300 ?
C13 C14 1.371(6) ?
C14 C15 1.388(6) ?
C14 H14A 0.9300 ?
C15 H15A 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
N1 H1A O1 . 0.86 2.09 2.559(5) 113.9 yes
N2 H2A O2 . 0.86 1.95 2.678(5) 141.8 yes
C11 H11A O2 2_654 0.93 2.45 3.305(5) 152.1 yes
C15 H15A S . 0.93 2.56 3.225(5) 129.1 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
C6 C1 C2 C3 1.8(7)
Cl1 C1 C2 C3 -178.7(3)
C1 C2 C3 C4 -2.6(7)
C7 O1 C4 C3 8.1(6)
C7 O1 C4 C5 -174.2(4)
C2 C3 C4 O1 179.2(4)
C2 C3 C4 C5 1.6(7)
O1 C4 C5 C6 -177.6(4)
C3 C4 C5 C6 0.3(6)
O1 C4 C5 Cl2 2.3(5)
C3 C4 C5 Cl2 -179.9(3)
C2 C1 C6 C5 0.1(6)
Cl1 C1 C6 C5 -179.4(3)
C4 C5 C6 C1 -1.1(6)
Cl2 C5 C6 C1 179.0(3)
C4 O1 C7 C8 177.4(4)
C9 N1 C8 O2 0.0(7)
C9 N1 C8 C7 -180.0(4)
O1 C7 C8 O2 175.9(4)
O1 C7 C8 N1 -4.1(5)
C10 N2 C9 N1 176.0(4)
C10 N2 C9 S -4.5(7)
C8 N1 C9 N2 -1.5(6)
C8 N1 C9 S 178.8(3)
C9 N2 C10 C15 8.6(7)
C9 N2 C10 C11 -172.8(4)
C15 C10 C11 C12 -1.2(7)
N2 C10 C11 C12 -179.9(4)
C10 C11 C12 C13 0.0(7)
C11 C12 C13 C14 1.0(6)
C11 C12 C13 N3 179.7(4)
O4 N3 C13 C14 18.4(6)
O3 N3 C13 C14 -163.9(4)
O4 N3 C13 C12 -160.4(4)
O3 N3 C13 C12 17.3(6)
C12 C13 C14 C15 -0.8(6)
N3 C13 C14 C15 -179.5(4)
C11 C10 C15 C14 1.4(6)
N2 C10 C15 C14 179.9(4)
C13 C14 C15 C10 -0.4(7)
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 3821315
