# Supplementary Material (ESI) for Dalton Transactions
# This journal is (c) The Royal Society of Chemistry 2009

data_global
_journal_name_full               'Dalton Trans.'

_journal_coden_Cambridge         0182

_publ_contact_author_name        'Vladimir Arion'
_publ_contact_author_email       VLADIMIR.ARION@UNIVIE.AC.AT

_publ_section_title              
;
Fluorescence properties and cellular distribution
of the investigational anti-cancer drug triapine
(3-aminopyridine-2-carboxaldehyde thiosemicarbazone) and its
zinc(II) complex
;
loop_
_publ_author_name
'Vladimir Arion'
'Michael Jakupec'
'Bernhard Keppler'
'Christian R. Kowol'
'Irene K Lichtscheidl'
;
R.Trondl
;

# Attachment 'CHKO468.CIF'

data_CHKO468
_database_code_depnum_ccdc_archive 'CCDC 732708'
_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
3-Aminopyridine-2-carbaldehyde-thiosemicarbazone-dichlorido-zinc(II)
monoethanol solvate
;
_chemical_name_common            
;
3-Aminopyridine-2-carbaldehyde-thiosemicarbazone-dichlorido-
zinc(ii) monoethanol solvate
;
_chemical_melting_point          ?
_chemical_formula_moiety         'C7 H9 Cl2 N5 S Zn, C2 H6 O'
_chemical_formula_sum            'C9 H15 Cl2 N5 O S Zn'
_chemical_formula_weight         377.59

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'
Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Zn Zn 0.2839 1.4301 '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'

_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_H-M   P21/c
_symmetry_space_group_name_Hall  '-P 2ybc'
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'

_cell_length_a                   11.4639(7)
_cell_length_b                   10.2716(5)
_cell_length_c                   12.7509(7)
_cell_angle_alpha                90.00
_cell_angle_beta                 99.422(4)
_cell_angle_gamma                90.00
_cell_volume                     1481.20(14)
_cell_formula_units_Z            4
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    888
_cell_measurement_theta_min      2.61
_cell_measurement_theta_max      30.47

_exptl_crystal_description       plate
_exptl_crystal_colour            yellow
_exptl_crystal_size_max          0.20
_exptl_crystal_size_mid          0.10
_exptl_crystal_size_min          0.03
_exptl_crystal_density_meas      'not measured'
_exptl_crystal_density_diffrn    1.693
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             768
_exptl_absorpt_coefficient_mu    2.158
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.6721
_exptl_absorpt_correction_T_max  0.9381
_exptl_absorpt_process_details   SADABS

_exptl_special_details           
;
?
;

_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Bruker X8 APEXII CCD'
_diffrn_measurement_method       ?
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            61508
_diffrn_reflns_av_R_equivalents  0.0692
_diffrn_reflns_av_sigmaI/netI    0.0328
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_theta_min         2.56
_diffrn_reflns_theta_max         30.10
_reflns_number_total             4342
_reflns_number_gt                3376
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    ?
_computing_publication_material  ?

_refine_special_details          
;
Refinement of F^2^ against ALL reflections. The weighted R-factor wR and
goodness of fit S are based on F^2^, conventional R-factors R are based
on F, with F set to zero for negative F^2^. The threshold expression of
F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is
not relevant to the choice of reflections for refinement. R-factors based
on F^2^ are statistically about twice as large as those based on F, and R-
factors based on ALL data will be even larger.
;

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[\s^2^(Fo^2^)+(0.0247P)^2^+1.1069P] where P=(Fo^2^+2Fc^2^)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         4342
_refine_ls_number_parameters     173
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0461
_refine_ls_R_factor_gt           0.0274
_refine_ls_wR_factor_ref         0.0642
_refine_ls_wR_factor_gt          0.0573
_refine_ls_goodness_of_fit_ref   1.005
_refine_ls_restrained_S_all      1.005
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000

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 0.193671(19) 0.92318(2) 0.204256(17) 0.01462(6) Uani 1 1 d . . .
Cl1 Cl 0.34243(4) 1.01522(5) 0.13304(4) 0.02421(11) Uani 1 1 d . . .
Cl2 Cl 0.22135(4) 0.91794(4) 0.38728(3) 0.01809(10) Uani 1 1 d . . .
S1 S 0.05291(4) 1.11039(4) 0.17083(4) 0.01681(10) Uani 1 1 d . . .
N1 N 0.23901(14) 0.72270(15) 0.18457(12) 0.0162(3) Uani 1 1 d . . .
N2 N 0.06772(15) 0.42647(15) 0.10681(13) 0.0192(3) Uani 1 1 d . . .
H2A H -0.0034 0.4588 0.0861 0.023 Uiso 1 1 calc R . .
H2B H 0.0794 0.3419 0.1043 0.023 Uiso 1 1 calc R . .
N3 N 0.03291(14) 0.83293(14) 0.13066(12) 0.0139(3) Uani 1 1 d . . .
N4 N -0.07124(14) 0.89856(14) 0.10345(12) 0.0154(3) Uani 1 1 d . . .
H4 H -0.1370 0.8567 0.0789 0.018 Uiso 1 1 calc R . .
N5 N -0.17203(14) 1.09005(15) 0.08115(13) 0.0179(3) Uani 1 1 d . . .
H5A H -0.2347 1.0452 0.0527 0.022 Uiso 1 1 calc R . .
H5B H -0.1765 1.1752 0.0870 0.022 Uiso 1 1 calc R . .
C1 C 0.34607(18) 0.6724(2) 0.21353(16) 0.0222(4) Uani 1 1 d . . .
H1 H 0.4101 0.7288 0.2392 0.027 Uiso 1 1 calc R . .
C2 C 0.36726(18) 0.5396(2) 0.20730(16) 0.0238(4) Uani 1 1 d . . .
H2 H 0.4450 0.5061 0.2269 0.029 Uiso 1 1 calc R . .
C3 C 0.27489(18) 0.45734(19) 0.17257(15) 0.0201(4) Uani 1 1 d . . .
H3 H 0.2883 0.3664 0.1685 0.024 Uiso 1 1 calc R . .
C4 C 0.16017(17) 0.50770(18) 0.14289(14) 0.0164(4) Uani 1 1 d . . .
C5 C 0.14710(16) 0.64345(17) 0.14879(14) 0.0139(3) Uani 1 1 d . . .
C6 C 0.03408(16) 0.70868(17) 0.11818(14) 0.0143(3) Uani 1 1 d . . .
H6 H -0.0355 0.6618 0.0903 0.017 Uiso 1 1 calc R . .
C7 C -0.07082(17) 1.02930(17) 0.11520(14) 0.0149(4) Uani 1 1 d . . .
O1 O 0.26169(13) 0.22851(14) 0.42513(15) 0.0327(4) Uani 1 1 d . . .
H1A H 0.2528 0.1474 0.4218 0.049 Uiso 1 1 calc R . .
C8 C 0.37973(19) 0.2608(2) 0.41121(18) 0.0278(5) Uani 1 1 d . . .
H8A H 0.3874 0.3567 0.4081 0.033 Uiso 1 1 calc R . .
H8B H 0.3948 0.2247 0.3427 0.033 Uiso 1 1 calc R . .
C9 C 0.47101(19) 0.2088(2) 0.49954(19) 0.0302(5) Uani 1 1 d . . .
H9A H 0.5501 0.2341 0.4872 0.045 Uiso 1 1 calc R . .
H9B H 0.4655 0.1136 0.5015 0.045 Uiso 1 1 calc R . .
H9C H 0.4569 0.2448 0.5675 0.045 Uiso 1 1 calc R . .

loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_23
_atom_site_aniso_U_13
_atom_site_aniso_U_12
Zn1 0.01782(11) 0.01258(10) 0.01330(10) -0.00086(8) 0.00210(8) -0.00362(8)
Cl1 0.0200(2) 0.0292(3) 0.0231(2) 0.0045(2) 0.00238(19) -0.0092(2)
Cl2 0.0242(2) 0.0160(2) 0.0134(2) -0.00074(16) 0.00104(17) 0.00040(18)
S1 0.0214(2) 0.01043(19) 0.0179(2) -0.00044(16) 0.00111(18) -0.00164(17)
N1 0.0184(8) 0.0171(7) 0.0137(7) -0.0020(6) 0.0044(6) -0.0026(6)
N2 0.0243(9) 0.0085(7) 0.0231(8) 0.0001(6) -0.0013(7) 0.0008(6)
N3 0.0173(8) 0.0117(7) 0.0128(7) 0.0005(6) 0.0021(6) 0.0005(6)
N4 0.0159(8) 0.0112(7) 0.0180(8) -0.0010(6) -0.0005(6) -0.0007(6)
N5 0.0204(8) 0.0131(7) 0.0194(8) 0.0009(6) 0.0008(6) 0.0006(6)
C1 0.0186(10) 0.0275(11) 0.0202(10) -0.0030(8) 0.0022(8) -0.0015(8)
C2 0.0199(10) 0.0274(10) 0.0231(10) 0.0009(8) 0.0012(8) 0.0065(8)
C3 0.0252(10) 0.0175(9) 0.0177(9) 0.0004(7) 0.0036(8) 0.0060(8)
C4 0.0248(10) 0.0135(8) 0.0108(8) -0.0004(7) 0.0026(7) 0.0011(7)
C5 0.0173(9) 0.0134(8) 0.0112(8) -0.0011(6) 0.0033(7) -0.0007(7)
C6 0.0177(9) 0.0126(8) 0.0127(8) -0.0006(6) 0.0024(7) -0.0020(7)
C7 0.0218(9) 0.0126(8) 0.0109(8) 0.0006(6) 0.0046(7) -0.0003(7)
O1 0.0215(8) 0.0175(7) 0.0578(11) -0.0058(7) 0.0022(7) 0.0017(6)
C8 0.0247(11) 0.0273(11) 0.0312(11) 0.0014(9) 0.0040(9) 0.0016(9)
C9 0.0239(11) 0.0329(12) 0.0333(12) -0.0002(10) 0.0031(9) 0.0071(9)

_geom_special_details            
;
All esds (except the esd in the dihedral angle between two l.s. planes)
are estimated using the full covariance matrix. The cell esds are taken
into account individually in the estimation of esds in distances, angles
and torsion angles; correlations between esds in cell parameters are only
used when they are defined by crystal symmetry. An approximate (isotropic)
treatment of cell esds is used for estimating esds involving l.s. planes.
;

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 2.1378(15) . ?
Zn1 N1 2.1486(16) . ?
Zn1 Cl1 2.2657(5) . ?
Zn1 Cl2 2.3038(5) . ?
Zn1 S1 2.5016(5) . ?
S1 C7 1.6970(19) . ?
N1 C1 1.327(3) . ?
N1 C5 1.350(2) . ?
N2 C4 1.368(2) . ?
N2 H2A 0.8800 . ?
N2 H2B 0.8800 . ?
N3 C6 1.286(2) . ?
N3 N4 1.366(2) . ?
N4 C7 1.351(2) . ?
N4 H4 0.8800 . ?
N5 C7 1.326(2) . ?
N5 H5A 0.8800 . ?
N5 H5B 0.8800 . ?
C1 C2 1.391(3) . ?
C1 H1 0.9500 . ?
C2 C3 1.370(3) . ?
C2 H2 0.9500 . ?
C3 C4 1.406(3) . ?
C3 H3 0.9500 . ?
C4 C5 1.406(2) . ?
C5 C6 1.454(3) . ?
C6 H6 0.9500 . ?
O1 C8 1.432(3) . ?
O1 H1A 0.8400 . ?
C8 C9 1.504(3) . ?
C8 H8A 0.9900 . ?
C8 H8B 0.9900 . ?
C9 H9A 0.9800 . ?
C9 H9B 0.9800 . ?
C9 H9C 0.9800 . ?

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 N1 74.97(6) . . ?
N3 Zn1 Cl1 131.02(4) . . ?
N1 Zn1 Cl1 98.09(4) . . ?
N3 Zn1 Cl2 113.60(4) . . ?
N1 Zn1 Cl2 95.74(4) . . ?
Cl1 Zn1 Cl2 115.33(2) . . ?
N3 Zn1 S1 76.87(4) . . ?
N1 Zn1 S1 151.46(4) . . ?
Cl1 Zn1 S1 96.767(19) . . ?
Cl2 Zn1 S1 99.705(18) . . ?
C7 S1 Zn1 99.54(6) . . ?
C1 N1 C5 119.62(17) . . ?
C1 N1 Zn1 124.81(13) . . ?
C5 N1 Zn1 115.27(12) . . ?
C4 N2 H2A 120.0 . . ?
C4 N2 H2B 120.0 . . ?
H2A N2 H2B 120.0 . . ?
C6 N3 N4 118.99(16) . . ?
C6 N3 Zn1 117.31(13) . . ?
N4 N3 Zn1 123.54(11) . . ?
C7 N4 N3 118.38(15) . . ?
C7 N4 H4 120.8 . . ?
N3 N4 H4 120.8 . . ?
C7 N5 H5A 120.0 . . ?
C7 N5 H5B 120.0 . . ?
H5A N5 H5B 120.0 . . ?
N1 C1 C2 121.89(19) . . ?
N1 C1 H1 119.1 . . ?
C2 C1 H1 119.1 . . ?
C3 C2 C1 119.36(19) . . ?
C3 C2 H2 120.3 . . ?
C1 C2 H2 120.3 . . ?
C2 C3 C4 119.97(18) . . ?
C2 C3 H3 120.0 . . ?
C4 C3 H3 120.0 . . ?
N2 C4 C5 122.65(17) . . ?
N2 C4 C3 120.34(17) . . ?
C5 C4 C3 116.98(17) . . ?
N1 C5 C4 122.13(17) . . ?
N1 C5 C6 115.12(16) . . ?
C4 C5 C6 122.74(17) . . ?
N3 C6 C5 116.80(17) . . ?
N3 C6 H6 121.6 . . ?
C5 C6 H6 121.6 . . ?
N5 C7 N4 116.38(17) . . ?
N5 C7 S1 122.17(14) . . ?
N4 C7 S1 121.45(14) . . ?
C8 O1 H1A 109.5 . . ?
O1 C8 C9 112.37(19) . . ?
O1 C8 H8A 109.1 . . ?
C9 C8 H8A 109.1 . . ?
O1 C8 H8B 109.1 . . ?
C9 C8 H8B 109.1 . . ?
H8A C8 H8B 107.9 . . ?
C8 C9 H9A 109.5 . . ?
C8 C9 H9B 109.5 . . ?
H9A C9 H9B 109.5 . . ?
C8 C9 H9C 109.5 . . ?
H9A C9 H9C 109.5 . . ?
H9B C9 H9C 109.5 . . ?

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 C7 0.99(7) . . . . ?
N1 Zn1 S1 C7 10.63(11) . . . . ?
Cl1 Zn1 S1 C7 131.61(6) . . . . ?
Cl2 Zn1 S1 C7 -111.17(6) . . . . ?
N3 Zn1 N1 C1 179.81(16) . . . . ?
Cl1 Zn1 N1 C1 49.40(16) . . . . ?
Cl2 Zn1 N1 C1 -67.26(15) . . . . ?
S1 Zn1 N1 C1 170.09(12) . . . . ?
N3 Zn1 N1 C5 -6.41(12) . . . . ?
Cl1 Zn1 N1 C5 -136.82(12) . . . . ?
Cl2 Zn1 N1 C5 106.52(12) . . . . ?
S1 Zn1 N1 C5 -16.13(19) . . . . ?
N1 Zn1 N3 C6 5.68(13) . . . . ?
Cl1 Zn1 N3 C6 93.37(14) . . . . ?
Cl2 Zn1 N3 C6 -84.08(14) . . . . ?
S1 Zn1 N3 C6 -179.07(14) . . . . ?
N1 Zn1 N3 N4 -178.93(14) . . . . ?
Cl1 Zn1 N3 N4 -91.25(14) . . . . ?
Cl2 Zn1 N3 N4 91.31(13) . . . . ?
S1 Zn1 N3 N4 -3.68(12) . . . . ?
C6 N3 N4 C7 -178.85(16) . . . . ?
Zn1 N3 N4 C7 5.8(2) . . . . ?
C5 N1 C1 C2 0.6(3) . . . . ?
Zn1 N1 C1 C2 174.13(15) . . . . ?
N1 C1 C2 C3 -1.5(3) . . . . ?
C1 C2 C3 C4 0.5(3) . . . . ?
C2 C3 C4 N2 179.14(18) . . . . ?
C2 C3 C4 C5 1.3(3) . . . . ?
C1 N1 C5 C4 1.3(3) . . . . ?
Zn1 N1 C5 C4 -172.85(13) . . . . ?
C1 N1 C5 C6 -179.39(17) . . . . ?
Zn1 N1 C5 C6 6.5(2) . . . . ?
N2 C4 C5 N1 179.99(17) . . . . ?
C3 C4 C5 N1 -2.2(3) . . . . ?
N2 C4 C5 C6 0.7(3) . . . . ?
C3 C4 C5 C6 178.54(17) . . . . ?
N4 N3 C6 C5 -179.75(15) . . . . ?
Zn1 N3 C6 C5 -4.1(2) . . . . ?
N1 C5 C6 N3 -1.6(2) . . . . ?
C4 C5 C6 N3 177.69(17) . . . . ?
N3 N4 C7 N5 175.59(15) . . . . ?
N3 N4 C7 S1 -4.5(2) . . . . ?
Zn1 S1 C7 N5 -178.67(14) . . . . ?
Zn1 S1 C7 N4 1.44(16) . . . . ?

_diffrn_measured_fraction_theta_max 0.999
_diffrn_reflns_theta_full        30.10
_diffrn_measured_fraction_theta_full 0.999
_refine_diff_density_max         0.449
_refine_diff_density_min         -0.478
_refine_diff_density_rms         0.083