#------------------------------------------------------------------------------
#$Date: 2016-02-20 22:30:07 +0200 (Sat, 20 Feb 2016) $
#$Revision: 176789 $
#$URL: svn://www.crystallography.net/cod/cif/2/22/04/2220476.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_2220476
loop_
_publ_author_name
'Khawar Rauf, M.'
'Bolte, Michael'
'Badshah, Amin'
_publ_section_title
;
 1-(2,6-Dichlorobenzoyl)-3-(3-methoxyphenyl)thiourea
;
_journal_coeditor_code           DN2414
_journal_issue                   1
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o142
_journal_paper_doi               10.1107/S1600536808041263
_journal_volume                  65
_journal_year                    2009
_chemical_formula_iupac          'C15 H12 Cl2 N2 O2 S'
_chemical_formula_moiety         'C15 H12 Cl2 N2 O2 S'
_chemical_formula_sum            'C15 H12 Cl2 N2 O2 S'
_chemical_formula_weight         355.23
_chemical_name_systematic
;
1-(2,6-Dichlorobenzoyl)-3-(3-methoxyphenyl)thiourea
;
_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           SHELXL-97
_cell_angle_alpha                90.00
_cell_angle_beta                 104.447(4)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   10.7215(6)
_cell_length_b                   11.2370(8)
_cell_length_c                   13.8065(8)
_cell_measurement_reflns_used    7361
_cell_measurement_temperature    173(2)
_cell_measurement_theta_max      28.2
_cell_measurement_theta_min      3.5
_cell_volume                     1610.77(18)
_computing_cell_refinement       'X-Area (Stoe & Cie, 2001)'
_computing_data_collection       'X-Area (Stoe & Cie, 2001)'
_computing_data_reduction        'X-Area (Stoe & Cie, 2001)'
_computing_molecular_graphics    'XP in SHELXTL-Plus (Sheldrick, 2008)'
_computing_publication_material  'SHELXL97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      173(2)
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measurement_device_type  'STOE IPDS II two-circle-diffractometer'
_diffrn_measurement_method       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  0.0604
_diffrn_reflns_av_sigmaI/netI    0.0341
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            19919
_diffrn_reflns_theta_full        25.00
_diffrn_reflns_theta_max         28.60
_diffrn_reflns_theta_min         3.55
_exptl_absorpt_coefficient_mu    0.539
_exptl_absorpt_correction_T_max  0.7973
_exptl_absorpt_correction_T_min  0.7856
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(MULABS; Spek, 2003; Blessing, 1995)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.465
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             728
_exptl_crystal_size_max          0.47
_exptl_crystal_size_mid          0.47
_exptl_crystal_size_min          0.44
_refine_diff_density_max         0.326
_refine_diff_density_min         -0.332
_refine_ls_extinction_coef       0.0178(13)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     SHELXL
_refine_ls_goodness_of_fit_ref   1.072
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     218
_refine_ls_number_reflns         4113
_refine_ls_number_restraints     2
_refine_ls_restrained_S_all      1.072
_refine_ls_R_factor_all          0.0399
_refine_ls_R_factor_gt           0.0347
_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)+(0.0324P)²+0.7918P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0850
_refine_ls_wR_factor_ref         0.0874
_reflns_number_gt                3704
_reflns_number_total             4113
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            dn2414.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        1610.77(17)
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               2220476
_cod_database_fobs_code          2220476
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_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_disorder_assembly
_atom_site_disorder_group
S S1 0.10910(3) 0.40403(4) 0.62296(3) 0.02598(11) Uani d . 1 . .
Cl Cl1 0.19499(5) 0.79513(4) 0.43009(3) 0.03990(12) Uani d . 1 . .
Cl Cl2 0.19839(4) 0.38864(4) 0.22155(3) 0.03747(12) Uani d . 1 . .
O O1 0.37925(9) 0.51869(10) 0.42963(7) 0.0259(2) Uani d . 1 . .
O O2 0.41731(16) 0.32269(15) 0.95663(9) 0.0556(4) Uani d D 1 . .
N N1 0.18818(11) 0.50043(11) 0.47460(8) 0.0194(2) Uani d . 1 . .
H H1 0.1077(18) 0.5144(16) 0.4543(13) 0.021(4) Uiso d . 1 . .
N N2 0.35139(11) 0.41869(11) 0.60087(8) 0.0190(2) Uani d . 1 . .
H H2 0.400(2) 0.4382(19) 0.5596(16) 0.038(5) Uiso d . 1 . .
C C1 0.26337(12) 0.53548(12) 0.41218(9) 0.0177(2) Uani d . 1 . .
C C2 0.22582(12) 0.44147(12) 0.56675(9) 0.0175(2) Uani d . 1 . .
C C11 0.18968(12) 0.59740(12) 0.31805(9) 0.0179(2) Uani d . 1 . .
C C12 0.15568(14) 0.71706(13) 0.31802(11) 0.0238(3) Uani d . 1 . .
C C13 0.09316(16) 0.77639(16) 0.23118(13) 0.0348(4) Uani d . 1 . .
H H13 0.0715 0.8582 0.2331 0.042 Uiso calc R 1 . .
C C14 0.06301(18) 0.71414(19) 0.14161(13) 0.0419(5) Uani d . 1 . .
H H14 0.0199 0.7535 0.0817 0.050 Uiso calc R 1 . .
C C15 0.09516(17) 0.59545(18) 0.13874(11) 0.0377(4) Uani d . 1 . .
H H15 0.0740 0.5534 0.0771 0.045 Uiso calc R 1 . .
C C16 0.15873(14) 0.53731(14) 0.22639(10) 0.0241(3) Uani d . 1 . .
C C21 0.41141(12) 0.35406(12) 0.69003(9) 0.0179(2) Uani d . 1 A .
C C22 0.38111(14) 0.37739(14) 0.78086(10) 0.0247(3) Uani d . 1 . .
H H22 0.3202 0.4371 0.7856 0.030 Uiso calc R 1 A .
C C23 0.44246(16) 0.31089(15) 0.86431(10) 0.0294(3) Uani d D 1 A .
C C24 0.53374(15) 0.22526(14) 0.85823(11) 0.0285(3) Uani d . 1 . .
H H24 0.5747 0.1802 0.9156 0.034 Uiso calc R 1 A .
C C25 0.56442(15) 0.20629(14) 0.76804(11) 0.0267(3) Uani d . 1 A .
H H25 0.6280 0.1489 0.7640 0.032 Uiso calc R 1 . .
C C26 0.50342(13) 0.27027(13) 0.68283(10) 0.0219(3) Uani d . 1 . .
H H26 0.5246 0.2566 0.6209 0.026 Uiso calc R 1 A .
C C27 0.3347(12) 0.4200(12) 0.9700(4) 0.067(2) Uani d PD 0.76(3) A 1
H H27A 0.3239 0.4185 1.0384 0.101 Uiso calc PR 0.76(3) A 1
H H27B 0.2505 0.4117 0.9224 0.101 Uiso calc PR 0.76(3) A 1
H H27C 0.3739 0.4957 0.9582 0.101 Uiso calc PR 0.76(3) A 1
C C27' 0.293(2) 0.374(2) 0.9566(14) 0.050(4) Uani d PD 0.24(3) A 2
H H27D 0.2833 0.3776 1.0254 0.075 Uiso calc PR 0.24(3) A 2
H H27E 0.2241 0.3237 0.9163 0.075 Uiso calc PR 0.24(3) A 2
H H27F 0.2864 0.4540 0.9282 0.075 Uiso calc PR 0.24(3) A 2
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'
Cl Cl 0.1484 0.1585 '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_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle
_geom_angle_publ_flag
C23 O2 C27' . . 115.5(7) ?
C23 O2 C27 . . 117.3(3) ?
C1 N1 C2 . . 128.51(11) ?
C1 N1 H1 . . 116.4(12) ?
C2 N1 H1 . . 115.1(12) ?
C2 N2 C21 . . 126.59(11) ?
C2 N2 H2 . . 115.4(13) ?
C21 N2 H2 . . 117.6(13) ?
O1 C1 N1 . . 123.98(12) ?
O1 C1 C11 . . 121.95(11) ?
N1 C1 C11 . . 114.07(11) ?
N2 C2 N1 . . 116.58(11) ?
N2 C2 S1 . . 126.15(10) ?
N1 C2 S1 . . 117.27(9) ?
C12 C11 C16 . . 117.55(12) ?
C12 C11 C1 . . 121.67(12) ?
C16 C11 C1 . . 120.70(12) ?
C13 C12 C11 . . 122.22(15) ?
C13 C12 Cl1 . . 118.95(13) ?
C11 C12 Cl1 . . 118.82(10) ?
C14 C13 C12 . . 118.84(16) ?
C14 C13 H13 . . 120.6 ?
C12 C13 H13 . . 120.6 ?
C15 C14 C13 . . 120.57(14) ?
C15 C14 H14 . . 119.7 ?
C13 C14 H14 . . 119.7 ?
C14 C15 C16 . . 119.94(16) ?
C14 C15 H15 . . 120.0 ?
C16 C15 H15 . . 120.0 ?
C15 C16 C11 . . 120.87(15) ?
C15 C16 Cl2 . . 119.39(12) ?
C11 C16 Cl2 . . 119.74(11) ?
C26 C21 C22 . . 121.43(12) ?
C26 C21 N2 . . 117.20(11) ?
C22 C21 N2 . . 121.34(12) ?
C23 C22 C21 . . 118.32(13) ?
C23 C22 H22 . . 120.8 ?
C21 C22 H22 . . 120.8 ?
O2 C23 C24 . . 115.28(13) ?
O2 C23 C22 . . 123.66(14) ?
C24 C23 C22 . . 121.05(13) ?
C25 C24 C23 . . 119.40(13) ?
C25 C24 H24 . . 120.3 ?
C23 C24 H24 . . 120.3 ?
C24 C25 C26 . . 120.92(13) ?
C24 C25 H25 . . 119.5 ?
C26 C25 H25 . . 119.5 ?
C21 C26 C25 . . 118.84(12) ?
C21 C26 H26 . . 120.6 ?
C25 C26 H26 . . 120.6 ?
O2 C27 H27A . . 109.5 ?
O2 C27 H27B . . 109.5 ?
H27A C27 H27B . . 109.5 ?
O2 C27 H27C . . 109.5 ?
H27A C27 H27C . . 109.5 ?
H27B C27 H27C . . 109.5 ?
O2 C27' H27D . . 109.5 ?
O2 C27' H27E . . 109.5 ?
H27D C27' H27E . . 109.5 ?
O2 C27' H27F . . 109.5 ?
H27D C27' H27F . . 109.5 ?
H27E C27' H27F . . 109.5 ?
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_site_symmetry_2
_geom_bond_distance
_geom_bond_publ_flag
S1 C2 . 1.6822(13) ?
Cl1 C12 . 1.7367(16) ?
Cl2 C16 . 1.7293(16) ?
O1 C1 . 1.2198(16) ?
O2 C23 . 1.3735(17) ?
O2 C27' . 1.454(12) ?
O2 C27 . 1.448(5) ?
N1 C1 . 1.3763(16) ?
N1 C2 . 1.4015(16) ?
N1 H1 . 0.852(18) ?
N2 C2 . 1.3355(16) ?
N2 C21 . 1.4358(15) ?
N2 H2 . 0.89(2) ?
C1 C11 . 1.5116(17) ?
C11 C12 . 1.393(2) ?
C11 C16 . 1.3993(19) ?
C12 C13 . 1.389(2) ?
C13 C14 . 1.387(3) ?
C13 H13 . 0.9500 ?
C14 C15 . 1.381(3) ?
C14 H14 . 0.9500 ?
C15 C16 . 1.394(2) ?
C15 H15 . 0.9500 ?
C21 C26 . 1.3852(19) ?
C21 C22 . 1.3965(18) ?
C22 C23 . 1.3930(19) ?
C22 H22 . 0.9500 ?
C23 C24 . 1.390(2) ?
C24 C25 . 1.382(2) ?
C24 H24 . 0.9500 ?
C25 C26 . 1.3946(19) ?
C25 H25 . 0.9500 ?
C26 H26 . 0.9500 ?
C27 H27A . 0.9800 ?
C27 H27B . 0.9800 ?
C27 H27C . 0.9800 ?
C27' H27D . 0.9800 ?
C27' H27E . 0.9800 ?
C27' H27F . 0.9800 ?
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 H2 O1 . 0.89(2) 1.97(2) 2.7007(15) 137.9(18)
N2 H2 O1 3_666 0.89(2) 2.38(2) 3.1015(16) 137.8(18)
N1 H1 S1 3_566 0.852(18) 2.479(19) 3.3141(12) 166.7(16)
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_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion
_geom_torsion_publ_flag
C2 N1 C1 O1 . . . . 0.2(2) ?
C2 N1 C1 C11 . . . . 179.99(13) ?
C21 N2 C2 N1 . . . . -176.37(12) ?
C21 N2 C2 S1 . . . . 2.5(2) ?
C1 N1 C2 N2 . . . . 2.1(2) ?
C1 N1 C2 S1 . . . . -176.87(12) ?
O1 C1 C11 C12 . . . . -99.98(17) ?
N1 C1 C11 C12 . . . . 80.23(16) ?
O1 C1 C11 C16 . . . . 76.83(18) ?
N1 C1 C11 C16 . . . . -102.97(15) ?
C16 C11 C12 C13 . . . . 0.1(2) ?
C1 C11 C12 C13 . . . . 176.99(13) ?
C16 C11 C12 Cl1 . . . . -178.93(10) ?
C1 C11 C12 Cl1 . . . . -2.03(17) ?
C11 C12 C13 C14 . . . . 0.4(2) ?
Cl1 C12 C13 C14 . . . . 179.37(13) ?
C12 C13 C14 C15 . . . . -0.3(3) ?
C13 C14 C15 C16 . . . . -0.1(3) ?
C14 C15 C16 C11 . . . . 0.6(2) ?
C14 C15 C16 Cl2 . . . . -179.99(14) ?
C12 C11 C16 C15 . . . . -0.6(2) ?
C1 C11 C16 C15 . . . . -177.50(13) ?
C12 C11 C16 Cl2 . . . . -179.99(10) ?
C1 C11 C16 Cl2 . . . . 3.08(18) ?
C2 N2 C21 C26 . . . . 135.10(15) ?
C2 N2 C21 C22 . . . . -46.8(2) ?
C26 C21 C22 C23 . . . . -2.4(2) ?
N2 C21 C22 C23 . . . . 179.66(14) ?
C27' O2 C23 C24 . . . . -156.8(14) ?
C27 O2 C23 C24 . . . . 172.8(8) ?
C27' O2 C23 C22 . . . . 22.3(14) ?
C27 O2 C23 C22 . . . . -8.1(8) ?
C21 C22 C23 O2 . . . . -177.57(17) ?
C21 C22 C23 C24 . . . . 1.4(2) ?
O2 C23 C24 C25 . . . . 179.39(17) ?
C22 C23 C24 C25 . . . . 0.3(3) ?
C23 C24 C25 C26 . . . . -1.2(3) ?
C22 C21 C26 C25 . . . . 1.5(2) ?
N2 C21 C26 C25 . . . . 179.58(13) ?
C24 C25 C26 C21 . . . . 0.3(2) ?
