#------------------------------------------------------------------------------
#$Date: 2016-02-20 00:18:51 +0200 (Sat, 20 Feb 2016) $
#$Revision: 176760 $
#$URL: svn://www.crystallography.net/cod/cif/2/01/35/2013562.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_2013562
loop_
_publ_author_name
'Zhang, You-Ming'
'Xian, Liang'
'Wei, Tai-Bao'
_publ_section_title
Chlorobis[N'-ethoxycarbonyl-N-(4-methylphenyl)thiourea-κS]copper(I)
_journal_issue                   11
_journal_name_full               'Acta Crystallographica Section C'
_journal_page_first              m473
_journal_page_last               m474
_journal_paper_doi               10.1107/S0108270103022285
_journal_volume                  59
_journal_year                    2003
_chemical_formula_iupac          '[Cu Cl (C11 H14 N2 O2 S)2]'
_chemical_formula_moiety         'C22 H28 Cl Cu N4 O4 S2'
_chemical_formula_sum            'C22 H28 Cl Cu N4 O4 S2'
_chemical_formula_weight         575.59
_chemical_name_systematic
;
Chlorobis[N'-ethoxycarbonyl-N-(4-methylphenyl)thiourea-\kS]copper(I)
;
_space_group_IT_number           62
_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_Hall  '-P 2ac 2n'
_symmetry_space_group_name_H-M   'P n m a'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL97
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   22.826(7)
_cell_length_b                   6.971(2)
_cell_length_c                   16.593(5)
_cell_measurement_reflns_used    998
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      22.55
_cell_measurement_theta_min      2.95
_cell_volume                     2640.3(14)
_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, 1990)'
_diffrn_ambient_temperature      293(2)
_diffrn_measured_fraction_theta_full 0.994
_diffrn_measured_fraction_theta_max 0.994
_diffrn_measurement_device_type  'Make Model 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  0.068
_diffrn_reflns_av_sigmaI/netI    0.054
_diffrn_reflns_limit_h_max       28
_diffrn_reflns_limit_h_min       -27
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_number            14770
_diffrn_reflns_theta_full        26.42
_diffrn_reflns_theta_max         26.42
_diffrn_reflns_theta_min         1.52
_exptl_absorpt_coefficient_mu    1.121
_exptl_absorpt_correction_T_max  0.836
_exptl_absorpt_correction_T_min  0.542
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(SADABS; Bruker, 1998)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.448
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             1192
_exptl_crystal_size_max          0.30
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.16
_refine_diff_density_max         0.35
_refine_diff_density_min         -0.32
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.148
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     202
_refine_ls_number_reflns         2943
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.148
_refine_ls_R_factor_all          0.116
_refine_ls_R_factor_gt           0.059
_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)+(0.0741P)²+0.2626P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.131
_refine_ls_wR_factor_ref         0.161
_reflns_number_gt                1757
_reflns_number_total             2943
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            de1224.cif
_cod_data_source_block           I
_cod_depositor_comments
;
The following automatic conversions were performed:
'_symmetry_cell_setting' value 'Orthorhombic' changed to 'orthorhombic'
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 'Orthorhombic' changed to
'orthorhombic' 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 

The following automatic conversions were performed:

'_exptl_crystal_density_meas' value 'not measured' was changed to '?'
- the value is perceived as not measured.

Automatic conversion script
Id: cif_fix_values 3008 2015-01-20 13:52:24Z robertas 
;
_cod_original_cell_volume        2640.1(14)
_cod_original_sg_symbol_H-M      Pnma
_cod_database_code               2013562
_cod_database_fobs_code          2013562
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'-x, y+1/2, -z'
'x+1/2, -y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, y, -z-1/2'
'x, -y-1/2, z'
'-x-1/2, 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_disorder_assembly
_atom_site_disorder_group
_atom_site_type_symbol
Cu1 0.47544(3) 0.7500 0.32174(4) 0.0580(3) Uani d S 1 . . Cu
S1 0.45043(8) 0.7500 0.19262(9) 0.0654(6) Uani d S 1 . . S
S2 0.40543(6) 0.7500 0.41373(9) 0.0538(5) Uani d S 1 . . S
Cl1 0.57008(7) 0.7500 0.35843(10) 0.0833(7) Uani d S 1 . . Cl
N1 0.5099(2) 0.7500 0.0544(3) 0.0569(15) Uani d S 1 . . N
H1 0.5446 0.7500 0.0343 0.068 Uiso calc SR 1 . . H
N2 0.5649(2) 0.7500 0.1683(3) 0.0551(14) Uani d S 1 . . N
H2A 0.5659 0.7500 0.2201 0.066 Uiso calc SR 1 . . H
N3 0.4010(2) 0.7500 0.5717(3) 0.080(2) Uani d S 1 . . N
H3A 0.4190 0.7500 0.6172 0.096 Uiso calc SR 1 . . H
N4 0.4939(2) 0.7500 0.5183(3) 0.0460(13) Uani d S 1 . . N
H4 0.5154 0.7500 0.4757 0.055 Uiso calc SR 1 . . H
O1 0.6249(2) 0.7500 0.0579(3) 0.0832(16) Uani d S 1 . . O
O2 0.66131(19) 0.7500 0.1832(3) 0.0757(15) Uani d S 1 . . O
O3 0.4993(2) 0.7500 0.6561(3) 0.0928(19) Uani d S 1 . . O
O4 0.57942(16) 0.7500 0.5785(2) 0.0540(11) Uani d S 1 . . O
C1 0.4664(3) 0.7500 -0.0052(4) 0.0552(17) Uani d S 1 . . C
C2 0.4069(3) 0.7500 0.0070(4) 0.070(2) Uani d S 1 . . C
H2 0.3921 0.7500 0.0591 0.085 Uiso calc SR 1 . . H
C3 0.3692(3) 0.7500 -0.0577(4) 0.088(3) Uani d S 1 . . C
H3 0.3290 0.7500 -0.0482 0.106 Uiso calc SR 1 . . H
C4 0.3894(3) 0.7500 -0.1367(4) 0.0641(19) Uani d S 1 . . C
C5 0.4478(3) 0.7500 -0.1477(4) 0.072(2) Uani d S 1 . . C
H5 0.4628 0.7500 -0.1998 0.086 Uiso calc SR 1 . . H
C6 0.4857(3) 0.7500 -0.0837(4) 0.069(2) Uani d S 1 . . C
H6 0.5257 0.7500 -0.0937 0.082 Uiso calc SR 1 . . H
C7 0.3486(4) 0.7500 -0.2076(5) 0.092(3) Uani d S 1 . . C
H7A 0.3452 0.8779 -0.2285 0.138 Uiso calc PR 0.50 . . H
H7B 0.3107 0.7053 -0.1909 0.138 Uiso calc PR 0.50 . . H
H7C 0.3638 0.6667 -0.2487 0.138 Uiso calc PR 0.50 . . H
C8 0.5105(2) 0.7500 0.1331(4) 0.0509(16) Uani d S 1 . . C
C9 0.6179(3) 0.7500 0.1292(4) 0.0649(19) Uani d S 1 . . C
C10 0.7200(3) 0.7500 0.1477(5) 0.099(3) Uani d S 1 . . C
H10A 0.7258 0.8631 0.1146 0.119 Uiso calc PR 0.50 . . H
H10B 0.7258 0.6369 0.1146 0.119 Uiso calc PR 0.50 . . H
C11 0.7608(3) 0.7500 0.2167(5) 0.129(4) Uani d S 1 . . C
H11A 0.8004 0.7500 0.1972 0.193 Uiso calc SR 1 . . H
H11B 0.7542 0.6376 0.2488 0.193 Uiso calc PR 0.50 . . H
H11C 0.7542 0.8624 0.2488 0.193 Uiso calc PR 0.50 . . H
C12 0.3383(3) 0.7500 0.5751(4) 0.061(2) Uani d S 1 . . C
C13 0.3094(2) 0.5825(10) 0.5800(3) 0.0831(17) Uani d . 1 . . C
H13 0.3293 0.4668 0.5745 0.100 Uiso calc R 1 . . H
C14 0.2490(2) 0.5846(11) 0.5936(3) 0.0909(19) Uani d . 1 . . C
H14 0.2289 0.4687 0.5962 0.109 Uiso calc R 1 . . H
C15 0.2190(3) 0.7500 0.6028(4) 0.075(3) Uani d S 1 . . C
C16 0.1543(3) 0.7500 0.6234(5) 0.119(4) Uani d S 1 . . C
H16A 0.1477 0.8278 0.6703 0.178 Uiso calc PR 0.50 . . H
H16B 0.1417 0.6211 0.6340 0.178 Uiso calc PR 0.50 . . H
H16C 0.1324 0.8012 0.5789 0.178 Uiso calc PR 0.50 . . H
C17 0.4342(2) 0.7500 0.5071(3) 0.0454(15) Uani d S 1 . . C
C18 0.5224(3) 0.7500 0.5916(4) 0.0518(16) Uani d S 1 . . C
C19 0.6155(3) 0.7500 0.6510(4) 0.0623(19) Uani d S 1 . . C
H19A 0.6075 0.6370 0.6833 0.075 Uiso calc PR 0.50 . . H
H19B 0.6075 0.8630 0.6833 0.075 Uiso calc PR 0.50 . . H
C20 0.6773(3) 0.7500 0.6239(5) 0.093(3) Uani d S 1 . . C
H20A 0.6837 0.8562 0.5881 0.139 Uiso calc PR 0.50 . . H
H20B 0.6855 0.6322 0.5962 0.139 Uiso calc PR 0.50 . . H
H20C 0.7026 0.7616 0.6698 0.139 Uiso calc PR 0.50 . . 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'
Cu Cu 0.3201 1.2651 '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
S2 Cu1 S1 . 118.77(7)
S2 Cu1 Cl1 . 120.58(7)
S1 Cu1 Cl1 . 120.66(7)
C8 S1 Cu1 . 110.9(2)
C17 S2 Cu1 . 110.7(2)
C8 N1 C1 . 135.5(5)
C8 N1 H1 . 112.2
C1 N1 H1 . 112.2
C8 N2 C9 . 126.6(5)
C8 N2 H2A . 116.7
C9 N2 H2A . 116.7
C17 N3 C12 . 127.6(5)
C17 N3 H3A . 116.2
C12 N3 H3A . 116.2
C17 N4 C18 . 125.9(5)
C17 N4 H4 . 117.0
C18 N4 H4 . 117.0
C9 O2 C10 . 114.1(5)
C18 O4 C19 . 114.9(5)
C2 C1 C6 . 117.0(6)
C2 C1 N1 . 126.7(6)
C6 C1 N1 . 116.3(6)
C1 C2 C3 . 120.4(6)
C1 C2 H2 . 119.8
C3 C2 H2 . 119.8
C2 C3 C4 . 121.8(7)
C2 C3 H3 . 119.1
C4 C3 H3 . 119.1
C5 C4 C3 . 117.2(6)
C5 C4 C7 . 120.6(7)
C3 C4 C7 . 122.2(7)
C4 C5 C6 . 121.3(7)
C4 C5 H5 . 119.3
C6 C5 H5 . 119.3
C5 C6 C1 . 122.3(6)
C5 C6 H6 . 118.9
C1 C6 H6 . 118.9
C4 C7 H7A . 109.5
C4 C7 H7B . 109.5
H7A C7 H7B . 109.5
C4 C7 H7C . 109.5
H7A C7 H7C . 109.5
H7B C7 H7C . 109.5
N1 C8 N2 . 115.8(5)
N1 C8 S1 . 125.2(5)
N2 C8 S1 . 119.0(4)
O1 C9 O2 . 124.5(6)
O1 C9 N2 . 125.9(6)
O2 C9 N2 . 109.6(5)
O2 C10 C11 . 105.4(6)
O2 C10 H10A . 110.7
C11 C10 H10A . 110.7
O2 C10 H10B . 110.7
C11 C10 H10B . 110.7
H10A C10 H10B . 108.8
C10 C11 H11A . 109.5
C10 C11 H11B . 109.5
H11A C11 H11B . 109.5
C10 C11 H11C . 109.5
H11A C11 H11C . 109.5
H11B C11 H11C . 109.5
C13 C12 C13 7_575 120.8(7)
C13 C12 N3 7_575 119.5(3)
C13 C12 N3 . 119.5(3)
C12 C13 C14 . 119.0(6)
C12 C13 H13 . 120.5
C14 C13 H13 . 120.5
C15 C14 C13 . 121.9(6)
C15 C14 H14 . 119.0
C13 C14 H14 . 119.0
C14 C15 C14 7_575 117.2(7)
C14 C15 C16 7_575 121.4(4)
C14 C15 C16 . 121.4(4)
C15 C16 H16A . 109.5
C15 C16 H16B . 109.5
H16A C16 H16B . 109.5
C15 C16 H16C . 109.5
H16A C16 H16C . 109.5
H16B C16 H16C . 109.5
N3 C17 N4 . 117.5(5)
N3 C17 S2 . 121.7(4)
N4 C17 S2 . 120.8(4)
O3 C18 O4 . 125.7(5)
O3 C18 N4 . 125.6(6)
O4 C18 N4 . 108.7(5)
O4 C19 C20 . 106.7(6)
O4 C19 H19A . 110.4
C20 C19 H19A . 110.4
O4 C19 H19B . 110.4
C20 C19 H19B . 110.4
H19A C19 H19B . 108.6
C19 C20 H20A . 109.5
C19 C20 H20B . 109.5
H20A C20 H20B . 109.5
C19 C20 H20C . 109.5
H20A C20 H20C . 109.5
H20B C20 H20C . 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
Cu1 S2 . 2.2099(17) ?
Cu1 S1 . 2.2171(18) ?
Cu1 Cl1 . 2.2445(19) ?
S1 C8 . 1.689(6) ?
S2 C17 . 1.683(6) ?
N1 C8 . 1.306(8) ?
N1 C1 . 1.400(7) ?
N1 H1 . 0.8600 ?
N2 C8 . 1.373(7) ?
N2 C9 . 1.373(8) ?
N2 H2A . 0.8600 ?
N3 C17 . 1.312(8) ?
N3 C12 . 1.434(8) ?
N3 H3A . 0.8600 ?
N4 C17 . 1.374(7) ?
N4 C18 . 1.380(7) ?
N4 H4 . 0.8600 ?
O1 C9 . 1.192(8) ?
O2 C9 . 1.337(8) ?
O2 C10 . 1.464(8) ?
O3 C18 . 1.193(7) ?
O4 C18 . 1.319(7) ?
O4 C19 . 1.458(7) ?
C1 C2 . 1.373(9) ?
C1 C6 . 1.375(9) ?
C2 C3 . 1.376(9) ?
C2 H2 . 0.9300 ?
C3 C4 . 1.391(9) ?
C3 H3 . 0.9300 ?
C4 C5 . 1.345(10) ?
C4 C7 . 1.500(9) ?
C5 C6 . 1.369(9) ?
C5 H5 . 0.9300 ?
C6 H6 . 0.9300 ?
C7 H7A . 0.9600 ?
C7 H7B . 0.9600 ?
C7 H7C . 0.9600 ?
C10 C11 . 1.475(11) ?
C10 H10A . 0.9700 ?
C10 H10B . 0.9700 ?
C11 H11A . 0.9600 ?
C11 H11B . 0.9600 ?
C11 H11C . 0.9600 ?
C12 C13 7_575 1.343(7) ?
C12 C13 . 1.343(7) ?
C13 C14 . 1.397(7) ?
C13 H13 . 0.9300 ?
C14 C15 . 1.351(7) ?
C14 H14 . 0.9300 ?
C15 C14 7_575 1.351(7) ?
C15 C16 . 1.515(9) ?
C16 H16A . 0.9600 ?
C16 H16B . 0.9600 ?
C16 H16C . 0.9600 ?
C19 C20 . 1.480(9) ?
C19 H19A . 0.9700 ?
C19 H19B . 0.9700 ?
C20 H20A . 0.9600 ?
C20 H20B . 0.9600 ?
C20 H20C . 0.9600 ?
loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_publ_flag
N1 H1 O1 0.86 1.874 2.625 145 y
N2 H2A Cl1 0.86 2.297 3.157 179 y
N3 H3A O3 0.86 1.943 2.645 138 y
N4 H4 Cl1 0.86 2.313 3.172 178 y
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_4
_geom_torsion
S2 Cu1 S1 C8 . . 180.0
Cl1 Cu1 S1 C8 . . 0.0
S1 Cu1 S2 C17 . . 180.0
Cl1 Cu1 S2 C17 . . 0.0
C8 N1 C1 C2 . . 0.0
C8 N1 C1 C6 . . 180.0
C6 C1 C2 C3 . . 0.0
N1 C1 C2 C3 . . 180.0
C1 C2 C3 C4 . . 0.0
C2 C3 C4 C5 . . 0.0
C2 C3 C4 C7 . . 180.0
C3 C4 C5 C6 . . 0.0
C7 C4 C5 C6 . . 180.0
C4 C5 C6 C1 . . 0.0
C2 C1 C6 C5 . . 0.0
N1 C1 C6 C5 . . 180.0
C1 N1 C8 N2 . . 180.0
C1 N1 C8 S1 . . 0.0
C9 N2 C8 N1 . . 0.0
C9 N2 C8 S1 . . 180.0
Cu1 S1 C8 N1 . . 180.0
Cu1 S1 C8 N2 . . 0.0
C10 O2 C9 O1 . . 0.0
C10 O2 C9 N2 . . 180.0
C8 N2 C9 O1 . . 0.0
C8 N2 C9 O2 . . 180.0
C9 O2 C10 C11 . . 180.0
C17 N3 C12 C13 . 7_575 -92.7(5)
C17 N3 C12 C13 . . 92.7(5)
C13 C12 C13 C14 7_575 . -2.5(10)
N3 C12 C13 C14 . . 172.0(5)
C12 C13 C14 C15 . . -0.8(9)
C13 C14 C15 C14 . 7_575 4.0(11)
C13 C14 C15 C16 . . -175.6(6)
C12 N3 C17 N4 . . 180.0
C12 N3 C17 S2 . . 0.0000(10)
C18 N4 C17 N3 . . 0.0
C18 N4 C17 S2 . . 180.0
Cu1 S2 C17 N3 . . 180.0
Cu1 S2 C17 N4 . . 0.0
C19 O4 C18 O3 . . 0.0000(10)
C19 O4 C18 N4 . . 180.0
C17 N4 C18 O3 . . 0.0000(10)
C17 N4 C18 O4 . . 180.0
C18 O4 C19 C20 . . 180.0000(10)
