Impact of metal coordination on cytotoxicity of 3-aminopyridine-2-carboxaldehyde thiosemicarbazone (triapine) and novel insights into terminal dimethylation.
Kowol, Christian R.; Trondl, Robert; Heffeter, Petra; Arion, Vladimir B.; Jakupec, Michael A.; Roller, Alexander; Galanski, Markus; Berger, Walter; Keppler, Bernhard K.; Journal of medicinal chemistry 52 (2009) 5032–5043; doi:10.1021/jm900528d

data_1503671
_publ_section_title
;
 Impact of metal coordination on cytotoxicity of
 3-aminopyridine-2-carboxaldehyde thiosemicarbazone (triapine) and novel
 insights into terminal dimethylation.
;
_journal_issue                   16
_journal_name_full               'Journal of medicinal chemistry'
_journal_page_first              5032
_journal_page_last               5043
_journal_paper_doi               10.1021/jm900528d
_journal_volume                  52
_journal_year                    2009
_chemical_formula_moiety         'C14 H16 Ga N10 S2, C2 H6 O, N O3'
_chemical_formula_sum            'C16 H22 Ga N11 O4 S2'
_chemical_formula_weight         566.29
_chemical_name_systematic
; 
 ? 
;
_space_group_IT_number           2
_symmetry_cell_setting           triclinic
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                102.437(6)
_cell_angle_beta                 95.239(5)
_cell_angle_gamma                96.569(5)
_cell_formula_units_Z            2
_cell_length_a                   9.3441(7)
_cell_length_b                   9.7491(10)
_cell_length_c                   12.9501(13)
_cell_measurement_reflns_used    153
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      26.54
_cell_measurement_theta_min      2.87
_cell_volume                     1136.26(19)
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      296(2)
_diffrn_measured_fraction_theta_full 0.995
_diffrn_measured_fraction_theta_max 0.995
_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  0.1137
_diffrn_reflns_av_sigmaI/netI    0.1005
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            24622
_diffrn_reflns_theta_full        25.50
_diffrn_reflns_theta_max         25.50
_diffrn_reflns_theta_min         2.39
_exptl_absorpt_coefficient_mu    1.445
_exptl_absorpt_correction_T_max  0.9717
_exptl_absorpt_correction_T_min  0.9183
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   SADABS
_exptl_crystal_colour            orange
_exptl_crystal_density_diffrn    1.655
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             580
_exptl_crystal_size_max          0.06
_exptl_crystal_size_mid          0.05
_exptl_crystal_size_min          0.02
_refine_diff_density_max         1.224
_refine_diff_density_min         -0.981
_refine_diff_density_rms         0.123
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.000
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     314
_refine_ls_number_reflns         4226
_refine_ls_number_restraints     14
_refine_ls_restrained_S_all      1.019
_refine_ls_R_factor_all          0.1081
_refine_ls_R_factor_gt           0.0577
_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/[\s^2^(Fo^2^)+(0.0824P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1381
_refine_ls_wR_factor_ref         0.1526
_reflns_number_gt                2747
_reflns_number_total             4226
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            jm900528d_si_002.cif
_cod_data_source_block           chko263
_cod_original_cell_volume        1136.26(18)
_cod_original_sg_symbol_H-M      P-1
_cod_database_code               1503671