#------------------------------------------------------------------------------
#$Date: 2019-10-03 17:15:21 +0300 (Thu, 03 Oct 2019) $
#$Revision: 219077 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/01/34/7013406.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_7013406
loop_
_publ_author_name
'Blower, Philip J.'
'Castle, Thomas C.'
'Cowley, Andrew R.'
'Dilworth, Jonathan R.'
'Donnelly, Paul S.'
'Labisbal, Elena'
'Sowrey, Frank E.'
'Teat, Simon J.'
'Went, Michael J.'
_publ_section_title
;
 Structural trends in copper(II) bis(thiosemicarbazone) radiopharmaceuticals
;
_journal_coden_ASTM              DTARAF
_journal_issue                   23
_journal_name_full               'Dalton Transactions'
_journal_page_first              4416
_journal_page_last               4425
_journal_paper_doi               10.1039/b307499d
_journal_year                    2003
_chemical_formula_sum            'C10 H20 Cu N6 O S3'
_chemical_formula_weight         400.04
_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   difmap
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                90.00
_cell_angle_beta                 97.864(3)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   8.0485(13)
_cell_length_b                   14.086(2)
_cell_length_c                   15.071(2)
_cell_measurement_reflns_used    8401
_cell_measurement_temperature    150(2)
_cell_measurement_theta_max      29.29
_cell_measurement_theta_min      2.47
_cell_volume                     1692.5(4)
_computing_cell_refinement       'Bruker SAINT'
_computing_data_collection       'Bruker SMART'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL and local programs'
_computing_structure_refinement  'Bruker SHELXTL'
_computing_structure_solution    'Bruker SHELXTL'
_diffrn_ambient_temperature      150(2)
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.922
_diffrn_measurement_device_type  'Bruker SMART 1K CCD diffractometer'
_diffrn_measurement_method       'ω rotation with narrow frames'
_diffrn_radiation_monochromator  'silicon 111'
_diffrn_radiation_source         'Daresbury SRS station 9.8'
_diffrn_radiation_type           synchrotron
_diffrn_radiation_wavelength     0.6872
_diffrn_reflns_av_R_equivalents  0.0452
_diffrn_reflns_av_sigmaI/netI    0.0504
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       19
_diffrn_reflns_limit_k_min       -19
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_number            16313
_diffrn_reflns_theta_full        25.00
_diffrn_reflns_theta_max         29.38
_diffrn_reflns_theta_min         1.92
_diffrn_standards_decay_%        15
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    1.667
_exptl_absorpt_correction_T_max  0.96
_exptl_absorpt_correction_T_min  0.62
_exptl_absorpt_correction_type   multi-scan
_exptl_crystal_colour            orange/red
_exptl_crystal_density_diffrn    1.570
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       needle
_exptl_crystal_F_000             828
_exptl_crystal_size_max          0.30
_exptl_crystal_size_mid          0.03
_exptl_crystal_size_min          0.02
_refine_diff_density_max         0.461
_refine_diff_density_min         -0.364
_refine_diff_density_rms         0.090
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.040
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     196
_refine_ls_number_reflns         4753
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.040
_refine_ls_R_factor_all          0.0436
_refine_ls_R_factor_gt           0.0344
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0403P)²+0.3936P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0848
_refine_ls_wR_factor_ref         0.0899
_reflns_number_gt                3976
_reflns_number_total             4753
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            b307499d.txt
_cod_data_source_block           kent7
_cod_depositor_comments
;
 Updated bibliographic information.

 Antanas Vaitkus,
 2019-10-04
;
_cod_original_sg_symbol_H-M      P2(1)/c
_cod_database_code               7013406
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_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
Cu Cu 0.33333(3) 0.432877(16) 0.095127(14) 0.02354(8) Uani 1 1 d . . .
S1 S 0.30389(6) 0.47253(4) 0.23658(3) 0.02923(11) Uani 1 1 d . . .
C1 C 0.0721(3) 0.64900(15) -0.06121(13) 0.0329(4) Uani 1 1 d . . .
H1A H 0.0033 0.6730 -0.0173 0.049 Uiso 1 1 calc R . .
H1B H -0.0007 0.6300 -0.1158 0.049 Uiso 1 1 calc R . .
H1C H 0.1488 0.6990 -0.0756 0.049 Uiso 1 1 calc R . .
S2 S 0.47972(6) 0.29695(3) 0.09602(3) 0.02968(11) Uani 1 1 d . . .
C2 C 0.2363(3) 0.50950(15) -0.17905(12) 0.0311(4) Uani 1 1 d . . .
H2A H 0.3065 0.4619 -0.2034 0.047 Uiso 1 1 calc R . .
H2B H 0.2747 0.5732 -0.1927 0.047 Uiso 1 1 calc R . .
H2C H 0.1194 0.5013 -0.2062 0.047 Uiso 1 1 calc R . .
C11 C 0.1709(2) 0.56547(13) -0.02319(12) 0.0254(4) Uani 1 1 d . . .
N11 N 0.1968(2) 0.54576(11) 0.06170(10) 0.0244(3) Uani 1 1 d . . .
C12 C 0.1767(2) 0.57222(13) 0.20525(12) 0.0252(4) Uani 1 1 d . . .
N12 N 0.1315(2) 0.60261(11) 0.12238(10) 0.0258(3) Uani 1 1 d . . .
N13 N 0.1164(2) 0.61953(12) 0.27144(10) 0.0301(3) Uani 1 1 d . . .
H13 H 0.1460 0.6012 0.3272 0.036 Uiso 1 1 calc R . .
C13 C 0.0031(3) 0.70044(14) 0.25362(14) 0.0365(5) Uani 1 1 d . . .
H13A H 0.0671 0.7565 0.2400 0.055 Uiso 1 1 calc R . .
H13B H -0.0520 0.7132 0.3065 0.055 Uiso 1 1 calc R . .
H13C H -0.0820 0.6860 0.2025 0.055 Uiso 1 1 calc R . .
N21 N 0.3285(2) 0.42806(11) -0.03553(10) 0.0254(3) Uani 1 1 d . . .
C21 C 0.2488(2) 0.49746(14) -0.07986(11) 0.0259(4) Uani 1 1 d . . .
N22 N 0.4060(2) 0.35892(12) -0.07886(11) 0.0287(3) Uani 1 1 d . . .
C22 C 0.4816(2) 0.29615(13) -0.02109(13) 0.0276(4) Uani 1 1 d . . .
N23 N 0.5662(2) 0.22512(13) -0.05369(12) 0.0343(4) Uani 1 1 d . . .
H23 H 0.6176 0.1832 -0.0162 0.041 Uiso 1 1 calc R . .
C23 C 0.5758(3) 0.21500(16) -0.14919(15) 0.0418(5) Uani 1 1 d . . .
H23A H 0.4662 0.1954 -0.1803 0.063 Uiso 1 1 calc R . .
H23B H 0.6599 0.1669 -0.1581 0.063 Uiso 1 1 calc R . .
H23C H 0.6078 0.2759 -0.1734 0.063 Uiso 1 1 calc R . .
O1S O 0.21992(19) 0.56442(9) 0.45938(9) 0.0305(3) Uani 1 1 d . . .
S1S S 0.29323(6) 0.46578(3) 0.47768(3) 0.02683(11) Uani 1 1 d . . .
C1S C 0.2928(3) 0.44673(16) 0.59481(14) 0.0387(5) Uani 1 1 d . . .
H1S1 H 0.3730 0.4900 0.6288 0.058 Uiso 1 1 calc R . .
H1S2 H 0.3249 0.3809 0.6098 0.058 Uiso 1 1 calc R . .
H1S3 H 0.1802 0.4588 0.6101 0.058 Uiso 1 1 calc R . .
C2S C 0.1321(3) 0.38276(15) 0.43752(14) 0.0342(4) Uani 1 1 d . . .
H2S1 H 0.0314 0.3961 0.4654 0.051 Uiso 1 1 calc R . .
H2S2 H 0.1710 0.3181 0.4529 0.051 Uiso 1 1 calc R . .
H2S3 H 0.1054 0.3886 0.3723 0.051 Uiso 1 1 calc R . .
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'
Cu Cu 0.3201 1.2651 '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
S1 Cu S2 109.23(2) . . ?
S1 Cu N11 85.07(5) . . ?
S1 Cu N21 165.65(5) . . ?
S2 Cu N11 165.52(5) . . ?
S2 Cu N21 85.12(5) . . ?
N11 Cu N21 80.62(6) . . ?
Cu S1 C12 94.39(6) . . ?
H1A C1 H1B 109.5 . . ?
H1A C1 H1C 109.5 . . ?
H1A C1 C11 109.5 . . ?
H1B C1 H1C 109.5 . . ?
H1B C1 C11 109.5 . . ?
H1C C1 C11 109.5 . . ?
Cu S2 C22 94.34(7) . . ?
H2A C2 H2B 109.5 . . ?
H2A C2 H2C 109.5 . . ?
H2A C2 C21 109.5 . . ?
H2B C2 H2C 109.5 . . ?
H2B C2 C21 109.5 . . ?
H2C C2 C21 109.5 . . ?
C1 C11 N11 123.58(18) . . ?
C1 C11 C21 122.38(16) . . ?
N11 C11 C21 114.04(16) . . ?
Cu N11 C11 115.83(13) . . ?
Cu N11 N12 123.67(11) . . ?
C11 N11 N12 120.49(16) . . ?
S1 C12 N12 125.79(14) . . ?
S1 C12 N13 116.83(14) . . ?
N12 C12 N13 117.34(17) . . ?
N11 N12 C12 111.04(15) . . ?
C12 N13 H13 119.0 . . ?
C12 N13 C13 122.00(16) . . ?
H13 N13 C13 119.0 . . ?
N13 C13 H13A 109.5 . . ?
N13 C13 H13B 109.5 . . ?
N13 C13 H13C 109.5 . . ?
H13A C13 H13B 109.5 . . ?
H13A C13 H13C 109.5 . . ?
H13B C13 H13C 109.5 . . ?
Cu N21 C21 115.38(13) . . ?
Cu N21 N22 123.68(12) . . ?
C21 N21 N22 120.91(16) . . ?
C2 C21 C11 121.90(17) . . ?
C2 C21 N21 124.02(18) . . ?
C11 C21 N21 114.08(15) . . ?
N21 N22 C22 111.01(15) . . ?
S2 C22 N22 125.77(15) . . ?
S2 C22 N23 116.42(15) . . ?
N22 C22 N23 117.81(17) . . ?
C22 N23 H23 118.9 . . ?
C22 N23 C23 122.18(18) . . ?
H23 N23 C23 118.9 . . ?
N23 C23 H23A 109.5 . . ?
N23 C23 H23B 109.5 . . ?
N23 C23 H23C 109.5 . . ?
H23A C23 H23B 109.5 . . ?
H23A C23 H23C 109.5 . . ?
H23B C23 H23C 109.5 . . ?
O1S S1S C1S 105.27(9) . . ?
O1S S1S C2S 106.90(9) . . ?
C1S S1S C2S 97.86(11) . . ?
S1S C1S H1S1 109.5 . . ?
S1S C1S H1S2 109.5 . . ?
S1S C1S H1S3 109.5 . . ?
H1S1 C1S H1S2 109.5 . . ?
H1S1 C1S H1S3 109.5 . . ?
H1S2 C1S H1S3 109.5 . . ?
S1S C2S H2S1 109.5 . . ?
S1S C2S H2S2 109.5 . . ?
S1S C2S H2S3 109.5 . . ?
H2S1 C2S H2S2 109.5 . . ?
H2S1 C2S H2S3 109.5 . . ?
H2S2 C2S H2S3 109.5 . . ?
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
Cu S1 2.2474(6) . ?
Cu S2 2.2473(6) . ?
Cu N11 1.9592(16) . ?
Cu N21 1.9654(16) . ?
S1 C12 1.7636(19) . ?
C1 H1A 0.9800 . ?
C1 H1B 0.9800 . ?
C1 H1C 0.9800 . ?
C1 C11 1.490(3) . ?
S2 C22 1.7671(19) . ?
C2 H2A 0.9800 . ?
C2 H2B 0.9800 . ?
C2 H2C 0.9800 . ?
C2 C21 1.494(2) . ?
C11 N11 1.298(2) . ?
C11 C21 1.479(3) . ?
N11 N12 1.373(2) . ?
C12 N12 1.323(2) . ?
C12 N13 1.344(2) . ?
N13 H13 0.8800 . ?
N13 C13 1.462(3) . ?
C13 H13A 0.9800 . ?
C13 H13B 0.9800 . ?
C13 H13C 0.9800 . ?
N21 C21 1.303(2) . ?
N21 N22 1.369(2) . ?
N22 C22 1.329(3) . ?
C22 N23 1.341(2) . ?
N23 H23 0.8800 . ?
N23 C23 1.459(3) . ?
C23 H23A 0.9800 . ?
C23 H23B 0.9800 . ?
C23 H23C 0.9800 . ?
O1S S1S 1.5200(14) . ?
S1S C1S 1.786(2) . ?
S1S C2S 1.789(2) . ?
C1S H1S1 0.9800 . ?
C1S H1S2 0.9800 . ?
C1S H1S3 0.9800 . ?
C2S H2S1 0.9800 . ?
C2S H2S2 0.9800 . ?
C2S H2S3 0.9800 . ?
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
N13 H13 O1S 0.88 2.07 2.945(2) 177.4 .
N23 H23 O1S 0.88 2.22 3.072(2) 162.3 2_645
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
S2 Cu S1 C12 -176.22(6) . . . . ?
N11 Cu S1 C12 1.39(7) . . . . ?
N21 Cu S1 C12 5.6(2) . . . . ?
S1 Cu S2 C22 -177.34(6) . . . . ?
N11 Cu S2 C22 12.2(2) . . . . ?
N21 Cu S2 C22 2.21(7) . . . . ?
C1 C11 N11 Cu -179.22(14) . . . . ?
C1 C11 N11 N12 0.3(3) . . . . ?
C21 C11 N11 Cu 0.7(2) . . . . ?
C21 C11 N11 N12 -179.78(14) . . . . ?
S1 Cu N11 C11 177.53(13) . . . . ?
S1 Cu N11 N12 -1.98(13) . . . . ?
S2 Cu N11 C11 -11.5(3) . . . . ?
S2 Cu N11 N12 168.96(12) . . . . ?
N21 Cu N11 C11 -1.41(13) . . . . ?
N21 Cu N11 N12 179.07(14) . . . . ?
Cu S1 C12 N12 -1.27(17) . . . . ?
Cu S1 C12 N13 176.52(13) . . . . ?
S1 C12 N12 N11 0.1(2) . . . . ?
N13 C12 N12 N11 -177.69(15) . . . . ?
Cu N11 N12 C12 1.6(2) . . . . ?
C11 N11 N12 C12 -177.90(16) . . . . ?
S1 C12 N13 C13 -176.98(15) . . . . ?
N12 C12 N13 C13 1.0(3) . . . . ?
S1 Cu N21 C21 -2.3(3) . . . . ?
S1 Cu N21 N22 176.11(12) . . . . ?
S2 Cu N21 C21 179.44(13) . . . . ?
S2 Cu N21 N22 -2.17(13) . . . . ?
N11 Cu N21 C21 1.96(13) . . . . ?
N11 Cu N21 N22 -179.64(14) . . . . ?
Cu N21 C21 C2 177.36(14) . . . . ?
Cu N21 C21 C11 -2.1(2) . . . . ?
N22 N21 C21 C2 -1.1(3) . . . . ?
N22 N21 C21 C11 179.43(15) . . . . ?
C1 C11 C21 C2 1.4(3) . . . . ?
C1 C11 C21 N21 -179.14(17) . . . . ?
N11 C11 C21 C2 -178.55(16) . . . . ?
N11 C11 C21 N21 1.0(2) . . . . ?
Cu N21 N22 C22 0.7(2) . . . . ?
C21 N21 N22 C22 179.06(16) . . . . ?
N21 N22 C22 S2 2.0(2) . . . . ?
N21 N22 C22 N23 -178.58(15) . . . . ?
Cu S2 C22 N22 -3.08(17) . . . . ?
Cu S2 C22 N23 177.47(13) . . . . ?
S2 C22 N23 C23 179.04(15) . . . . ?
N22 C22 N23 C23 -0.5(3) . . . . ?
