#------------------------------------------------------------------------------
#$Date: 2016-03-23 01:51:24 +0200 (Wed, 23 Mar 2016) $
#$Revision: 179158 $
#$URL: svn://www.crystallography.net/cod/cif/4/31/19/4311965.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_4311965
loop_
_publ_author_name
'Monica Baldini'
'Marisa Belicchi-Ferrari'
'Franco Bisceglie'
'Pier Paolo Dall'Aglio'
'Giorgio Pelosi'
'Silvana Pinelli'
'Pieralberto Tarasconi'
_publ_section_title
;
 Copper(II) Complexes with Substituted Thiosemicarbazones of
 α-Ketoglutaric Acid: Synthesis, X-ray Structures, DNA Binding Studies,
 and Nuclease and Biological Activity
;
_journal_name_full               'Inorganic Chemistry'
_journal_page_first              7170
_journal_page_last               7179
_journal_paper_doi               10.1021/ic049883b
_journal_volume                  43
_journal_year                    2004
_chemical_formula_sum            'C9 H13 N3 O4 S'
_chemical_formula_weight         259.28
_chemical_melting_point          172.5
_chemical_name_systematic
;
4-allyl-1-alphaketoglutaric acid thiosemicarbazone
;
_space_group_IT_number           14
_symmetry_space_group_name_Hall  '-P 2yn'
_symmetry_space_group_name_H-M   'P 1 21/n 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_cell_angle_alpha                90.000(0)
_cell_angle_beta                 91.86(2)
_cell_angle_gamma                90.000(0)
_cell_formula_units_Z            4
_cell_length_a                   13.227(3)
_cell_length_b                   5.269(1)
_cell_length_c                   18.927(3)
_cell_measurement_temperature    293(2)
_cell_volume                     1318.4(4)
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_diffrn_ambient_temperature      293(2)
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71069
_diffrn_reflns_av_R_equivalents  0.1041
_diffrn_reflns_av_sigmaI/netI    0.1592
_diffrn_reflns_limit_h_max       18
_diffrn_reflns_limit_h_min       -18
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_l_max       26
_diffrn_reflns_limit_l_min       0
_diffrn_reflns_number            7690
_diffrn_reflns_theta_full        30.01
_diffrn_reflns_theta_max         30.00
_diffrn_reflns_theta_min         3.00
_exptl_absorpt_coefficient_mu    0.253
_exptl_crystal_density_diffrn    1.306
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             544
_refine_diff_density_max         0.181
_refine_diff_density_min         -0.153
_refine_diff_density_rms         0.041
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.749
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     177
_refine_ls_number_reflns         3847
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.749
_refine_ls_R_factor_all          0.2096
_refine_ls_R_factor_gt           0.0442
_refine_ls_shift/su_max          0.239
_refine_ls_shift/su_mean         0.024
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0545P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0991
_refine_ls_wR_factor_ref         0.1412
_reflns_number_gt                1044
_reflns_number_total             3847
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ic049883bsi20040729_123239_2.cif
_cod_data_source_block           3
_cod_database_code               4311965
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, -y-1/2, z-1/2'
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
S1 S -0.09895(6) 0.14626(17) 0.76563(5) 0.0765(3) Uani 1 1 d . . .
O1 O -0.06413(15) -0.7178(4) 0.53274(11) 0.0618(6) Uani 1 1 d . . .
O2 O 0.08586(16) -0.9009(4) 0.55574(11) 0.0677(6) Uani 1 1 d . . .
O3 O 0.3949(2) -0.3452(6) 0.64571(15) 0.1159(12) Uani 1 1 d . . .
O4 O 0.33740(15) -0.6277(4) 0.72123(12) 0.0767(7) Uani 1 1 d . . .
N1 N -0.17355(18) -0.0605(5) 0.64804(13) 0.0658(7) Uani 1 1 d . . .
H1 H -0.1712 -0.1769 0.6163 0.079 Uiso 1 1 calc R . .
N2 N -0.02249(16) -0.2235(5) 0.68875(12) 0.0567(7) Uani 1 1 d . . .
H2 H 0.0297 -0.2221 0.7170 0.068 Uiso 1 1 calc R . .
N3 N -0.03016(17) -0.3916(5) 0.63523(12) 0.0529(6) Uani 1 1 d . . .
C1 C -0.1007(2) -0.0534(5) 0.69708(15) 0.0557(8) Uani 1 1 d . . .
C2 C 0.0407(2) -0.5554(5) 0.62704(14) 0.0502(7) Uani 1 1 d . . .
C3 C 0.0232(2) -0.7386(6) 0.56794(15) 0.0518(7) Uani 1 1 d . . .
C4 C 0.1379(2) -0.5818(5) 0.66929(14) 0.0541(8) Uani 1 1 d . . .
H3 H 0.1548 -0.7602 0.6741 0.065 Uiso 1 1 calc R . .
H4 H 0.1294 -0.5130 0.7163 0.065 Uiso 1 1 calc R . .
C5 C 0.2238(2) -0.4434(6) 0.63410(16) 0.0658(9) Uani 1 1 d . . .
H5 H 0.2282 -0.5017 0.5857 0.079 Uiso 1 1 calc R . .
H6 H 0.2094 -0.2629 0.6330 0.079 Uiso 1 1 calc R . .
C6 C 0.3225(2) -0.4873(7) 0.67230(19) 0.0662(9) Uani 1 1 d . . .
C7 C -0.2581(3) 0.1177(9) 0.6444(3) 0.0849(12) Uani 1 1 d . . .
C8 C -0.3208(4) 0.0783(13) 0.5804(3) 0.147(2) Uani 1 1 d . . .
C9 C -0.3298(16) -0.134(4) 0.5454(14) 0.136(8) Uiso 0.25 1 d P . .
C10 C -0.3621(17) 0.228(4) 0.5405(11) 0.115(6) Uiso 0.25 1 d P . .
C11 C -0.4009(16) 0.110(4) 0.5610(11) 0.118(6) Uiso 0.25 1 d P . .
C12 C -0.3325(19) 0.025(5) 0.5255(13) 0.132(8) Uiso 0.25 1 d P . .
H7 H -0.073(3) -0.857(7) 0.503(2) 0.126(15) Uiso 1 1 d . . .
H8 H -0.294(2) 0.088(5) 0.6850(15) 0.070(10) Uiso 1 1 d . . .
H9 H -0.238(3) 0.285(10) 0.630(2) 0.17(2) Uiso 1 1 d . . .
H10 H 0.443(3) -0.353(8) 0.670(2) 0.125(18) Uiso 1 1 d . . .
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'
S S 0.1246 0.1234 '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'
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
C1 N1 C7 123.9(3) . . ?
N3 N2 C1 118.3(2) . . ?
C2 N3 N2 119.6(2) . . ?
N1 C1 N2 115.8(3) . . ?
N1 C1 S1 123.8(2) . . ?
N2 C1 S1 120.4(2) . . ?
N3 C2 C3 115.3(3) . . ?
N3 C2 C4 127.9(3) . . ?
C3 C2 C4 116.8(3) . . ?
O2 C3 O1 123.5(3) . . ?
O2 C3 C2 120.4(3) . . ?
O1 C3 C2 116.0(3) . . ?
C2 C4 C5 111.2(2) . . ?
C6 C5 C4 111.6(3) . . ?
O4 C6 O3 122.6(3) . . ?
O4 C6 C5 126.2(3) . . ?
O3 C6 C5 111.1(3) . . ?
C8 C7 N1 111.2(4) . . ?
C11 C8 C12 67.7(15) . . ?
C11 C8 C10 45.4(11) . . ?
C12 C8 C10 61.4(14) . . ?
C11 C8 C9 83.8(15) . . ?
C12 C8 C9 44.2(14) . . ?
C10 C8 C9 102.2(16) . . ?
C11 C8 C7 139.0(13) . . ?
C12 C8 C7 153.2(15) . . ?
C10 C8 C7 131.0(13) . . ?
C9 C8 C7 125.7(13) . . ?
C12 C9 C8 55(2) . . ?
C12 C9 C11 49(2) . . ?
C8 C9 C11 43.3(10) . . ?
C12 C9 C10 24(2) . . ?
C8 C9 C10 37.2(9) . . ?
C11 C9 C10 27.2(8) . . ?
C11 C10 C8 62(2) . . ?
C11 C10 C12 71(2) . . ?
C8 C10 C12 53.9(14) . . ?
C11 C10 C9 55(2) . . ?
C8 C10 C9 40.6(10) . . ?
C12 C10 C9 18.5(15) . . ?
C10 C11 C8 73(2) . . ?
C10 C11 C12 65(2) . . ?
C8 C11 C12 54.6(15) . . ?
C10 C11 C9 97(2) . . ?
C8 C11 C9 52.8(12) . . ?
C12 C11 C9 34.2(15) . . ?
C9 C12 C8 81(3) . . ?
C9 C12 C10 138(3) . . ?
C8 C12 C10 64.7(18) . . ?
C9 C12 C11 97(3) . . ?
C8 C12 C11 57.7(15) . . ?
C10 C12 C11 44.1(14) . . ?
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
S1 C1 1.670(3) . ?
O1 C3 1.319(3) . ?
O2 C3 1.219(3) . ?
O3 C6 1.328(4) . ?
O4 C6 1.197(4) . ?
N1 C1 1.317(3) . ?
N1 C7 1.461(4) . ?
N2 N3 1.347(3) . ?
N2 C1 1.381(3) . ?
N3 C2 1.288(3) . ?
C2 C3 1.490(4) . ?
C2 C4 1.498(4) . ?
C4 C5 1.521(4) . ?
C5 C6 1.490(4) . ?
C7 C8 1.460(6) . ?
C8 C11 1.12(2) . ?
C8 C12 1.08(2) . ?
C8 C10 1.21(2) . ?
C8 C9 1.30(2) . ?
C9 C12 0.92(3) . ?
C9 C11 1.63(3) . ?
C9 C10 1.96(3) . ?
C10 C11 0.90(2) . ?
C10 C12 1.18(3) . ?
C11 C12 1.23(3) . ?
