#------------------------------------------------------------------------------
#$Date: 2016-03-23 03:41:20 +0200 (Wed, 23 Mar 2016) $
#$Revision: 179257 $
#$URL: svn://www.crystallography.net/cod/cif/4/31/77/4317748.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/
#
# All data on this site have been placed in the public domain by the
# contributors.
#
data_4317748
loop_
_publ_author_name
'José S. Casas'
'María V. Castaño'
'Eduardo E. Castellano'
'Javier Ellena'
'María S. García-Tasende'
'Ángeles Gato'
'Agustín Sánchez'
'Luisa M. Sanjuán'
'José Sordo'
_publ_section_title
;
 Metal-Induced Cyclization of Thiosemicarbazones Derived from β-Keto
 Amides and β-Keto Esters: Open-Chain and Cyclized Ligands in Zinc(II)
 Complexes
;
_journal_name_full               'Inorganic Chemistry'
_journal_page_first              1550
_journal_page_last               1557
_journal_paper_doi               10.1021/ic0111942
_journal_volume                  41
_journal_year                    2002
_chemical_formula_sum            'C16 H30 N6 O5 S4 Zn'
_chemical_formula_weight         580.07
_chemical_name_systematic
;
 ?
;
_space_group_IT_number           12
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-C 2y'
_symmetry_space_group_name_H-M   'C 1 2/m 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                 100.17(3)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   15.266(9)
_cell_length_b                   20.072(5)
_cell_length_c                   8.2770(10)
_cell_measurement_reflns_used    25
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      36
_cell_measurement_theta_min      19
_cell_volume                     2496.4(16)
_computing_cell_refinement       'CAD4 Express (Enraf Nonius, 1994)'
_computing_data_collection       'CAD4 Express (Enraf Nonius, 1994)'
_computing_data_reduction        'XCAD4 (Harms & Wocadlo, 1995)'
_computing_molecular_graphics    'Ortep-3 for Windows (Farrugia, 1997)'
_computing_publication_material  'WinGX publication routines (Farrugia, 1999)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      293(2)
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measurement_device_type  'Enraf Nonius CAD4'
_diffrn_measurement_method       'non-profiled omega/2theta scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0155
_diffrn_reflns_av_sigmaI/netI    0.0232
_diffrn_reflns_limit_h_max       18
_diffrn_reflns_limit_h_min       0
_diffrn_reflns_limit_k_max       23
_diffrn_reflns_limit_k_min       0
_diffrn_reflns_limit_l_max       9
_diffrn_reflns_limit_l_min       -9
_diffrn_reflns_number            2378
_diffrn_reflns_theta_full        67.03
_diffrn_reflns_theta_max         67.03
_diffrn_reflns_theta_min         3.67
_diffrn_standards_decay_%        10
_diffrn_standards_interval_time  30
_diffrn_standards_number         1
_exptl_absorpt_coefficient_mu    4.837
_exptl_absorpt_correction_T_max  0.6098
_exptl_absorpt_correction_T_min  0.4368
_exptl_absorpt_correction_type   psi-scan
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.543
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             1208
_exptl_crystal_size_max          0.325
_exptl_crystal_size_mid          0.175
_exptl_crystal_size_min          0.075
_refine_diff_density_max         0.834
_refine_diff_density_min         -0.672
_refine_diff_density_rms         0.079
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.045
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     166
_refine_ls_number_reflns         2289
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.045
_refine_ls_R_factor_all          0.0577
_refine_ls_R_factor_gt           0.0442
_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)+(0.0837P)²+3.3981P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1209
_refine_ls_wR_factor_ref         0.1297
_reflns_number_gt                1868
_reflns_number_total             2289
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ic0111942_4.cif
_cod_data_source_block           '[Zn(L2)2(H2O)].2DMSO'
_cod_database_code               4317748
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y, -z'
'x+1/2, y+1/2, z'
'-x+1/2, y+1/2, -z'
'-x, -y, -z'
'x, -y, z'
'-x+1/2, -y+1/2, -z'
'x+1/2, -y+1/2, z'
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
Zn1 Zn 0.0000 0.31985(3) 0.5000 0.0368(2) Uani 1 2 d S . .
S1 S 0.07959(6) 0.38060(5) 0.73086(11) 0.0500(3) Uani 1 1 d . . .
S1S S 0.03546(9) 0.0000 0.29771(19) 0.0595(4) Uani 1 2 d S . .
S2S S 0.32494(15) 0.02810(10) -0.1545(2) 0.0550(5) Uani 0.50 1 d P . .
O1 O 0.35138(14) 0.35951(12) 0.5479(3) 0.0414(5) Uani 1 1 d . . .
O1W O 0.0000 0.21561(16) 0.5000 0.0459(8) Uani 1 2 d S . .
H1O H 0.0445 0.1854 0.4946 0.055 Uiso 1 1 d R . .
O1S O 0.1014(3) 0.0000 0.1849(6) 0.0691(11) Uani 1 2 d S . .
O2S O 0.2641(3) 0.0000 -0.0376(5) 0.0702(12) Uani 1 2 d S . .
N1 N 0.25125(19) 0.40625(15) 0.7678(4) 0.0484(7) Uani 1 1 d . . .
H11 H 0.3025 0.4041 0.7385 0.058 Uiso 1 1 calc R . .
H12 H 0.2454 0.4271 0.8560 0.058 Uiso 1 1 calc R . .
N2 N 0.19631(16) 0.34542(12) 0.5394(3) 0.0329(5) Uani 1 1 d . . .
N3 N 0.12481(16) 0.31815(13) 0.4328(3) 0.0360(6) Uani 1 1 d . . .
C1 C 0.1823(2) 0.37781(15) 0.6783(4) 0.0360(7) Uani 1 1 d . . .
C2 C 0.1587(2) 0.29717(15) 0.3039(4) 0.0333(6) Uani 1 1 d . . .
C4 C 0.27641(19) 0.33907(15) 0.4719(4) 0.0321(6) Uani 1 1 d . . .
C3 C 0.2496(2) 0.30933(15) 0.3202(4) 0.0339(6) Uani 1 1 d . . .
C5 C 0.0994(2) 0.2652(2) 0.1640(4) 0.0490(9) Uani 1 1 d . . .
H51 H 0.0399 0.2630 0.1869 0.074 Uiso 1 1 calc R . .
H52 H 0.1203 0.2209 0.1484 0.074 Uiso 1 1 calc R . .
H53 H 0.0995 0.2909 0.0662 0.074 Uiso 1 1 calc R . .
C6 C 0.3079(2) 0.29448(19) 0.1962(4) 0.0447(8) Uani 1 1 d . . .
H61 H 0.2968 0.3265 0.1089 0.067 Uiso 1 1 calc R . .
H62 H 0.2950 0.2506 0.1523 0.067 Uiso 1 1 calc R . .
H63 H 0.3693 0.2968 0.2481 0.067 Uiso 1 1 calc R . .
C11S C -0.0387(3) -0.0667(2) 0.2312(7) 0.0746(13) Uani 1 1 d . . .
H11A H -0.0640 -0.0607 0.1175 0.112 Uiso 1 1 calc R . .
H11B H -0.0853 -0.0674 0.2952 0.112 Uiso 1 1 calc R . .
H11C H -0.0067 -0.1081 0.2449 0.112 Uiso 1 1 calc R . .
C21S C 0.2693(5) 0.0000 -0.3527(7) 0.0761(19) Uani 1 2 d S . .
H21A H 0.3113 -0.0022 -0.4264 0.114 Uiso 1 2 calc SR . .
H21B H 0.2226 0.0306 -0.3951 0.114 Uiso 0.50 1 calc PR . .
H21C H 0.2445 -0.0434 -0.3424 0.114 Uiso 0.50 1 calc PR . .
C22S C 0.4054(7) -0.0373(6) -0.1429(15) 0.103(4) Uani 0.50 1 d P . .
H22A H 0.4423 -0.0372 -0.0362 0.154 Uiso 0.50 1 calc PR . .
H22B H 0.4418 -0.0303 -0.2250 0.154 Uiso 0.50 1 calc PR . .
H22C H 0.3755 -0.0793 -0.1614 0.154 Uiso 0.50 1 calc PR . .
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 '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 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
S S 0.3331 0.5567 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Zn Zn -1.5491 0.6778 '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_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
N3 Zn1 N3 178.11(15) 2_556 . ?
N3 Zn1 O1W 89.06(7) 2_556 . ?
N3 Zn1 O1W 89.06(7) . . ?
N3 Zn1 S1 98.86(8) 2_556 . ?
N3 Zn1 S1 82.10(8) . . ?
O1W Zn1 S1 120.44(3) . . ?
N3 Zn1 S1 82.10(8) 2_556 2_556 ?
N3 Zn1 S1 98.86(8) . 2_556 ?
O1W Zn1 S1 120.44(3) . 2_556 ?
S1 Zn1 S1 119.13(6) . 2_556 ?
C1 S1 Zn1 98.01(11) . . ?
O1S S1S C11S 105.7(2) . . ?
O1S S1S C11S 105.7(2) . 6 ?
C11S S1S C11S 97.8(3) . 6 ?
O2S S2S C22S 100.4(4) . . ?
O2S S2S C21S 102.4(3) . . ?
C22S S2S C21S 91.6(5) . . ?
C1 N2 N3 119.9(2) . . ?
C1 N2 C4 129.6(3) . . ?
N3 N2 C4 110.2(2) . . ?
C2 N3 N2 105.1(2) . . ?
C2 N3 Zn1 136.3(2) . . ?
N2 N3 Zn1 118.58(18) . . ?
N1 C1 N2 117.0(3) . . ?
N1 C1 S1 121.8(2) . . ?
N2 C1 S1 121.2(2) . . ?
N3 C2 C3 112.9(3) . . ?
N3 C2 C5 119.4(3) . . ?
C3 C2 C5 127.7(3) . . ?
O1 C4 C3 133.1(3) . . ?
O1 C4 N2 122.1(3) . . ?
C3 C4 N2 104.8(3) . . ?
C4 C3 C2 107.0(3) . . ?
C4 C3 C6 126.1(3) . . ?
C2 C3 C6 126.9(3) . . ?
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Zn1 N3 2.077(3) 2_556 ?
Zn1 N3 2.077(3) . ?
Zn1 O1W 2.092(3) . ?
Zn1 S1 2.4072(11) . ?
Zn1 S1 2.4072(11) 2_556 ?
S1 C1 1.701(3) . ?
S1S O1S 1.489(4) . ?
S1S C11S 1.777(5) . ?
S1S C11S 1.777(5) 6 ?
S2S O2S 1.561(4) . ?
S2S C22S 1.789(9) . ?
S2S C21S 1.799(6) . ?
O1 C4 1.273(4) . ?
N1 C1 1.306(4) . ?
N2 C1 1.370(4) . ?
N2 N3 1.389(3) . ?
N2 C4 1.437(4) . ?
N3 C2 1.334(4) . ?
C2 C3 1.392(4) . ?
C2 C5 1.485(4) . ?
C4 C3 1.385(4) . ?
C3 C6 1.502(4) . ?
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_site_symmetry_A
O1W H1O O1 0.92 1.91 2.810(3) 165.2 7_556
N1 H11 O1 0.86 2.06 2.741(4) 135.0 .
N1 H11 O1S 0.86 2.44 2.905(4) 115.0 7_556
N1 H12 O2S 0.86 2.12 2.960(4) 165.5 7_556
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_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
N3 Zn1 S1 C1 177.18(13) 2_556 . . . ?
N3 Zn1 S1 C1 -1.18(13) . . . . ?
O1W Zn1 S1 C1 83.04(11) . . . . ?
S1 Zn1 S1 C1 -96.96(11) 2_556 . . . ?
C1 N2 N3 C2 173.5(3) . . . . ?
C4 N2 N3 C2 -1.2(3) . . . . ?
C1 N2 N3 Zn1 -5.7(4) . . . . ?
C4 N2 N3 Zn1 179.61(19) . . . . ?
N3 Zn1 N3 C2 63.9(3) 2_556 . . . ?
O1W Zn1 N3 C2 63.9(3) . . . . ?
S1 Zn1 N3 C2 -175.2(3) . . . . ?
S1 Zn1 N3 C2 -56.8(3) 2_556 . . . ?
N3 Zn1 N3 N2 -117.2(2) 2_556 . . . ?
O1W Zn1 N3 N2 -117.2(2) . . . . ?
S1 Zn1 N3 N2 3.7(2) . . . . ?
S1 Zn1 N3 N2 122.1(2) 2_556 . . . ?
N3 N2 C1 N1 -175.5(3) . . . . ?
C4 N2 C1 N1 -2.0(5) . . . . ?
N3 N2 C1 S1 4.5(4) . . . . ?
C4 N2 C1 S1 178.0(2) . . . . ?
Zn1 S1 C1 N1 178.7(3) . . . . ?
Zn1 S1 C1 N2 -1.3(3) . . . . ?
N2 N3 C2 C3 0.0(4) . . . . ?
Zn1 N3 C2 C3 178.9(2) . . . . ?
N2 N3 C2 C5 -179.7(3) . . . . ?
Zn1 N3 C2 C5 -0.8(5) . . . . ?
C1 N2 C4 O1 7.0(5) . . . . ?
N3 N2 C4 O1 -179.0(3) . . . . ?
C1 N2 C4 C3 -172.1(3) . . . . ?
N3 N2 C4 C3 1.9(3) . . . . ?
O1 C4 C3 C2 179.2(3) . . . . ?
N2 C4 C3 C2 -1.9(3) . . . . ?
O1 C4 C3 C6 -1.9(6) . . . . ?
N2 C4 C3 C6 177.0(3) . . . . ?
N3 C2 C3 C4 1.3(4) . . . . ?
C5 C2 C3 C4 -179.1(3) . . . . ?
N3 C2 C3 C6 -177.6(3) . . . . ?
C5 C2 C3 C6 2.0(6) . . . . ?
