#------------------------------------------------------------------------------
#$Date: 2016-02-20 05:06:23 +0200 (Sat, 20 Feb 2016) $
#$Revision: 176774 $
#$URL: svn://www.crystallography.net/cod/cif/2/20/78/2207873.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_2207873
loop_
_publ_author_name
'Liu, Guo-Hua'
'Xue, Yun-Ning'
'Xue, Si-Jia'
_publ_section_title
N'-(4-Chloro-6-methoxypyrimidin-2-yl)-N-[2-(2,4-dichlorophenoxy)propionyl]thiourea
_journal_coeditor_code           SG6044
_journal_issue                   1
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o133
_journal_page_last               o135
_journal_paper_doi               10.1107/S1600536805040869
_journal_volume                  62
_journal_year                    2006
_chemical_formula_iupac          'C15 H13 Cl3 N4 O3 S'
_chemical_formula_moiety         'C15 H13 Cl3 N4 O3 S'
_chemical_formula_sum            'C15 H13 Cl3 N4 O3 S'
_chemical_formula_weight         435.70
_chemical_name_systematic
;
N'-(4-Chloro-6-methoxypyrimidin-2-yl)-
N-[2-(2,4-dichlorophenoxy)propionyl]thiourea
;
_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                105.302(10)
_cell_angle_beta                 105.729(9)
_cell_angle_gamma                90.698(11)
_cell_formula_units_Z            2
_cell_length_a                   7.939(5)
_cell_length_b                   10.183(7)
_cell_length_c                   12.764(9)
_cell_measurement_reflns_used    763
_cell_measurement_temperature    298(2)
_cell_measurement_theta_max      54.00
_cell_measurement_theta_min      5.230
_cell_volume                     954.1(11)
_computing_cell_refinement       SMART
_computing_data_collection       'SMART (Bruker, 1998)'
_computing_data_reduction        'SAINT (Bruker, 1998)'
_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      298(2)
_diffrn_measured_fraction_theta_full 0.980
_diffrn_measured_fraction_theta_max 0.980
_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  0.0294
_diffrn_reflns_av_sigmaI/netI    0.0470
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            3986
_diffrn_reflns_theta_full        25.01
_diffrn_reflns_theta_max         25.01
_diffrn_reflns_theta_min         1.73
_diffrn_standards_decay_%        4.98
_exptl_absorpt_coefficient_mu    0.613
_exptl_absorpt_correction_T_max  0.9700
_exptl_absorpt_correction_T_min  0.9137
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(SADABS; Bruker, 1998)'
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.517
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       plate
_exptl_crystal_F_000             444
_exptl_crystal_size_max          0.15
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.05
_refine_diff_density_max         0.352
_refine_diff_density_min         -0.347
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.924
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     235
_refine_ls_number_reflns         3289
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.924
_refine_ls_R_factor_all          0.0818
_refine_ls_R_factor_gt           0.0517
_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)+(0.0803P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1254
_refine_ls_wR_factor_ref         0.1385
_reflns_number_gt                2056
_reflns_number_total             3289
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            sg6044.cif
_cod_data_source_block           5
_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               2207873
_cod_database_fobs_code          2207873
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
Cl1 1.0076(2) 0.18363(13) 0.50979(10) 0.1061(5) Uani d . 1 Cl
Cl2 1.25298(12) 0.53913(12) 0.32880(10) 0.0828(4) Uani d . 1 Cl
Cl3 0.54098(14) 0.97877(14) -0.36176(10) 0.0955(4) Uani d . 1 Cl
N1 0.9193(3) 0.6547(3) 0.0613(2) 0.0476(7) Uani d . 1 N
H1A 0.9959 0.6240 0.1088 0.057 Uiso calc R 1 H
N2 0.8628(3) 0.7666(3) -0.0768(2) 0.0474(7) Uani d . 1 N
H2B 0.7571 0.7362 -0.0850 0.057 Uiso calc R 1 H
N3 1.0360(3) 0.9066(3) -0.1330(2) 0.0488(7) Uani d . 1 N
N4 0.7243(3) 0.8685(3) -0.2104(2) 0.0529(7) Uani d . 1 N
O1 0.8935(3) 0.5490(2) 0.2157(2) 0.0558(6) Uani d . 1 O
O2 0.6221(3) 0.6516(3) -0.0110(2) 0.0600(7) Uani d . 1 O
O3 1.1951(3) 1.0461(3) -0.1932(2) 0.0659(7) Uani d . 1 O
S1 1.20328(11) 0.74398(10) 0.02729(8) 0.0601(3) Uani d . 1 S
C1 0.9687(6) 0.2914(4) 0.4211(3) 0.0678(11) Uani d . 1 C
C2 1.1087(6) 0.3628(4) 0.4124(3) 0.0669(11) Uani d . 1 C
H2A 1.2225 0.3541 0.4530 0.080 Uiso calc R 1 H
C3 1.0785(5) 0.4483(4) 0.3423(3) 0.0540(9) Uani d . 1 C
C4 0.9088(4) 0.4616(3) 0.2819(3) 0.0505(8) Uani d . 1 C
C5 0.7707(5) 0.3861(4) 0.2920(3) 0.0610(10) Uani d . 1 C
H5A 0.6564 0.3924 0.2507 0.073 Uiso calc R 1 H
C6 0.8006(6) 0.3017(4) 0.3624(3) 0.0691(11) Uani d . 1 C
H6A 0.7072 0.2524 0.3698 0.083 Uiso calc R 1 H
C7 0.7222(4) 0.5686(4) 0.1499(3) 0.0505(8) Uani d . 1 C
H7A 0.6538 0.4795 0.1146 0.061 Uiso calc R 1 H
C8 0.6249(5) 0.6609(4) 0.2211(3) 0.0665(10) Uani d . 1 C
H8A 0.6079 0.6208 0.2780 0.100 Uiso calc R 1 H
H8B 0.5127 0.6730 0.1739 0.100 Uiso calc R 1 H
H8C 0.6918 0.7481 0.2569 0.100 Uiso calc R 1 H
C9 0.7492(4) 0.6273(3) 0.0583(3) 0.0468(8) Uani d . 1 C
C10 0.9893(4) 0.7245(3) -0.0003(3) 0.0427(7) Uani d . 1 C
C11 0.8781(4) 0.8511(3) -0.1438(3) 0.0453(8) Uani d . 1 C
C12 0.7373(5) 0.9523(4) -0.2726(3) 0.0565(9) Uani d . 1 C
C13 0.8900(5) 1.0161(4) -0.2718(3) 0.0572(9) Uani d . 1 C
H13A 0.8933 1.0742 -0.3166 0.069 Uiso calc R 1 H
C14 1.0405(4) 0.9872(3) -0.1985(3) 0.0503(8) Uani d . 1 C
C15 1.3498(4) 1.0112(4) -0.1189(4) 0.0694(11) Uani d . 1 C
H15A 1.4524 1.0590 -0.1220 0.104 Uiso calc R 1 H
H15B 1.3583 0.9144 -0.1426 0.104 Uiso calc R 1 H
H15C 1.3413 1.0368 -0.0426 0.104 Uiso calc R 1 H
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
C9 N1 C10 130.5(3) yes
C9 N1 H1A 114.8 ?
C10 N1 H1A 114.8 ?
C10 N2 C11 129.9(3) ?
C10 N2 H2B 115.0 ?
C11 N2 H2B 115.0 ?
C14 N3 C11 115.6(3) ?
C11 N4 C12 113.4(3) ?
C4 O1 C7 119.5(2) ?
C14 O3 C15 116.8(3) ?
C6 C1 C2 121.8(4) ?
C6 C1 Cl1 119.4(3) ?
C2 C1 Cl1 118.8(3) ?
C1 C2 C3 119.0(4) ?
C1 C2 H2A 120.5 ?
C3 C2 H2A 120.5 ?
C2 C3 C4 120.6(3) ?
C2 C3 Cl2 120.1(3) ?
C4 C3 Cl2 119.3(3) ?
O1 C4 C5 125.5(3) ?
O1 C4 C3 115.9(3) ?
C5 C4 C3 118.6(3) ?
C6 C5 C4 120.7(4) ?
C6 C5 H5A 119.6 ?
C4 C5 H5A 119.6 ?
C1 C6 C5 119.2(4) ?
C1 C6 H6A 120.4 ?
C5 C6 H6A 120.4 ?
O1 C7 C8 112.1(3) ?
O1 C7 C9 106.9(2) yes
C8 C7 C9 111.0(3) ?
O1 C7 H7A 108.9 ?
C8 C7 H7A 108.9 ?
C9 C7 H7A 108.9 ?
C7 C8 H8A 109.5 ?
C7 C8 H8B 109.5 ?
H8A C8 H8B 109.5 ?
C7 C8 H8C 109.5 ?
H8A C8 H8C 109.5 ?
H8B C8 H8C 109.5 ?
O2 C9 N1 123.8(3) ?
O2 C9 C7 120.0(3) ?
N1 C9 C7 116.2(3) yes
N2 C10 N1 112.5(3) yes
N2 C10 S1 129.5(2) yes
N1 C10 S1 118.0(2) yes
N3 C11 N4 128.1(3) ?
N3 C11 N2 118.8(3) ?
N4 C11 N2 113.0(3) ?
N4 C12 C13 125.4(3) ?
N4 C12 Cl3 115.6(3) ?
C13 C12 Cl3 119.0(3) ?
C12 C13 C14 114.6(3) ?
C12 C13 H13A 122.7 ?
C14 C13 H13A 122.7 ?
N3 C14 O3 119.2(3) ?
N3 C14 C13 122.8(3) ?
O3 C14 C13 118.0(3) ?
O3 C15 H15A 109.5 ?
O3 C15 H15B 109.5 ?
H15A C15 H15B 109.5 ?
O3 C15 H15C 109.5 ?
H15A C15 H15C 109.5 ?
H15B C15 H15C 109.5 ?
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_publ_flag
Cl1 C1 1.748(4) ?
Cl2 C3 1.728(4) ?
Cl3 C12 1.734(4) ?
N1 C9 1.364(4) yes
N1 C10 1.398(4) yes
N1 H1A 0.8600 ?
N2 C10 1.358(4) yes
N2 C11 1.390(4) ?
N2 H2B 0.8600 ?
N3 C14 1.323(4) ?
N3 C11 1.326(4) ?
N4 C11 1.329(4) ?
N4 C12 1.330(4) ?
O1 C4 1.367(4) ?
O1 C7 1.439(4) ?
O2 C9 1.225(3) yes
O3 C14 1.337(4) ?
O3 C15 1.446(4) ?
S1 C10 1.637(3) yes
C1 C6 1.362(6) ?
C1 C2 1.365(6) ?
C2 C3 1.384(5) ?
C2 H2A 0.9300 ?
C3 C4 1.387(5) ?
C4 C5 1.384(5) ?
C5 C6 1.379(5) ?
C5 H5A 0.9300 ?
C6 H6A 0.9300 ?
C7 C8 1.502(5) ?
C7 C9 1.507(4) ?
C7 H7A 0.9800 ?
C8 H8A 0.9600 ?
C8 H8B 0.9600 ?
C8 H8C 0.9600 ?
C12 C13 1.364(5) ?
C13 C14 1.392(5) ?
C13 H13A 0.9300 ?
C15 H15A 0.9600 ?
C15 H15B 0.9600 ?
C15 H15C 0.9600 ?
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
C15 H15C N2 2_775 0.96 2.96 3.688(5) 134
C8 H8C O3 2_775 0.96 2.67 3.435(5) 138
C8 H8B S1 1_455 0.96 2.89 3.837(4) 171
C7 H7A S1 2_765 0.98 2.96 3.545(4) 120
C7 H7A O2 2_665 0.98 2.40 3.281(4) 150
N2 H2B O2 . 0.86 1.93 2.657(3) 141
N1 H1A O1 . 0.86 2.06 2.533(3) 114
