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#$Date: 2017-10-13 14:42:48 +0300 (Fri, 13 Oct 2017) $
#$Revision: 201982 $
#$URL: file:///home/coder/svn-repositories/cod/cif/4/30/65/4306501.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_4306501
loop_
_publ_author_name
'Christian R. Kowol'
'Erwin Reisner'
'Ion Chiorescu'
'Vladimir B. Arion'
'Markus Galanski'
'Dirk V. Deubel'
'Bernhard K. Keppler'
_publ_section_title
;
An Electrochemical Study of Antineoplastic Gallium, Iron and Ruthenium
Complexes with Redox Noninnocent α-N-Heterocyclic Chalcogensemicarbazones
;
_journal_name_full               'Inorganic Chemistry'
_journal_page_first              11032
_journal_page_last               11047
_journal_paper_doi               10.1021/ic8013249
_journal_volume                  47
_journal_year                    2008
_chemical_formula_sum            'C13 H13 N5 S'
_chemical_formula_weight         271.34
_chemical_name_systematic
; 
Acetylpyrazine ⁴N-phenylthiosemicarbazone
;
_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                76.005(12)
_cell_angle_beta                 87.021(9)
_cell_angle_gamma                89.220(9)
_cell_formula_units_Z            2
_cell_length_a                   5.7844(14)
_cell_length_b                   10.036(3)
_cell_length_c                   11.314(4)
_cell_measurement_reflns_used    605
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      28.44
_cell_measurement_theta_min      3.11
_cell_volume                     636.4(3)
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      100(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     0.71073
_diffrn_reflns_av_R_equivalents  0.1025
_diffrn_reflns_av_sigmaI/netI    0.0821
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            12257
_diffrn_reflns_theta_full        24.99
_diffrn_reflns_theta_max         24.99
_diffrn_reflns_theta_min         2.44
_exptl_absorpt_coefficient_mu    0.247
_exptl_absorpt_correction_T_max  0.9975
_exptl_absorpt_correction_T_min  0.9615
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   SADABS
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.416
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       needle
_exptl_crystal_F_000             284
_exptl_crystal_size_max          0.16
_exptl_crystal_size_mid          0.01
_exptl_crystal_size_min          0.01
_refine_diff_density_max         0.258
_refine_diff_density_min         -0.293
_refine_diff_density_rms         0.065
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.031
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     177
_refine_ls_number_reflns         2236
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.031
_refine_ls_R_factor_all          0.0899
_refine_ls_R_factor_gt           0.0440
_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)+(0.0331P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0828
_refine_ls_wR_factor_ref         0.0920
_reflns_number_gt                1473
_reflns_number_total             2236
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ic8013249_si_002_1.cif
_cod_data_source_block           CHKO135
_cod_original_cell_volume        636.5(3)
_cod_database_code               4306501
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -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
S1 S 1.46863(12) 0.59874(7) 0.64211(7) 0.0184(2) Uani 1 1 d . . .
N1 N 0.6892(4) 0.0435(2) 0.6192(2) 0.0193(6) Uani 1 1 d . . .
N2 N 0.3754(4) 0.1245(2) 0.7859(2) 0.0218(6) Uani 1 1 d . . .
N3 N 0.9661(4) 0.3415(2) 0.6540(2) 0.0157(5) Uani 1 1 d . . .
N4 N 1.1605(4) 0.4191(2) 0.6156(2) 0.0169(5) Uani 1 1 d . . .
H4 H 1.2466 0.4087 0.5521 0.020 Uiso 1 1 calc R . .
N5 N 1.0601(4) 0.5307(2) 0.7638(2) 0.0188(6) Uani 1 1 d . . .
H50 H 0.948(5) 0.484(3) 0.770(3) 0.028(9) Uiso 1 1 d . . .
C1 C 0.5074(5) -0.0329(3) 0.6702(3) 0.0228(7) Uani 1 1 d . . .
H1 H 0.4826 -0.1171 0.6485 0.027 Uiso 1 1 calc R . .
C2 C 0.3541(5) 0.0053(3) 0.7529(3) 0.0230(7) Uani 1 1 d . . .
H2 H 0.2292 -0.0543 0.7878 0.028 Uiso 1 1 calc R . .
C3 C 0.5562(4) 0.2011(3) 0.7333(2) 0.0187(7) Uani 1 1 d . . .
H3 H 0.5771 0.2873 0.7522 0.022 Uiso 1 1 calc R . .
C4 C 0.7156(4) 0.1613(3) 0.6523(2) 0.0156(6) Uani 1 1 d . . .
C5 C 0.9227(4) 0.2452(3) 0.6016(2) 0.0162(6) Uani 1 1 d . . .
C6 C 1.0678(5) 0.2089(3) 0.5004(3) 0.0223(7) Uani 1 1 d . . .
H6A H 1.0750 0.2876 0.4294 0.033 Uiso 1 1 calc R . .
H6B H 0.9989 0.1303 0.4780 0.033 Uiso 1 1 calc R . .
H6C H 1.2245 0.1850 0.5274 0.033 Uiso 1 1 calc R . .
C7 C 1.2178(4) 0.5132(3) 0.6785(2) 0.0157(6) Uani 1 1 d . . .
C8 C 1.0757(5) 0.6173(3) 0.8460(2) 0.0167(6) Uani 1 1 d . . .
C9 C 0.8863(5) 0.6990(3) 0.8611(3) 0.0212(7) Uani 1 1 d . . .
H9 H 0.7557 0.7017 0.8130 0.025 Uiso 1 1 calc R . .
C10 C 0.8898(5) 0.7769(3) 0.9476(3) 0.0222(7) Uani 1 1 d . . .
H10 H 0.7606 0.8330 0.9583 0.027 Uiso 1 1 calc R . .
C11 C 1.0782(5) 0.7735(3) 1.0173(3) 0.0224(7) Uani 1 1 d . . .
H11 H 1.0784 0.8259 1.0769 0.027 Uiso 1 1 calc R . .
C12 C 1.2683(5) 0.6930(3) 1.0002(2) 0.0215(7) Uani 1 1 d . . .
H12 H 1.4006 0.6923 1.0467 0.026 Uiso 1 1 calc R . .
C13 C 1.2659(5) 0.6138(3) 0.9156(2) 0.0210(7) Uani 1 1 d . . .
H13 H 1.3947 0.5571 0.9054 0.025 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'
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 C4 116.3(2) . . ?
C3 N2 C2 115.1(2) . . ?
C5 N3 N4 118.4(2) . . ?
C7 N4 N3 118.4(2) . . ?
C7 N4 H4 120.8 . . ?
N3 N4 H4 120.8 . . ?
C7 N5 C8 127.6(2) . . ?
C7 N5 H50 114(2) . . ?
C8 N5 H50 118(2) . . ?
N1 C1 C2 122.6(3) . . ?
N1 C1 H1 118.7 . . ?
C2 C1 H1 118.7 . . ?
N2 C2 C1 122.0(3) . . ?
N2 C2 H2 119.0 . . ?
C1 C2 H2 119.0 . . ?
N2 C3 C4 123.2(2) . . ?
N2 C3 H3 118.4 . . ?
C4 C3 H3 118.4 . . ?
N1 C4 C3 120.7(2) . . ?
N1 C4 C5 117.5(2) . . ?
C3 C4 C5 121.7(2) . . ?
N3 C5 C4 115.2(2) . . ?
N3 C5 C6 125.6(2) . . ?
C4 C5 C6 119.2(2) . . ?
C5 C6 H6A 109.5 . . ?
C5 C6 H6B 109.5 . . ?
H6A C6 H6B 109.5 . . ?
C5 C6 H6C 109.5 . . ?
H6A C6 H6C 109.5 . . ?
H6B C6 H6C 109.5 . . ?
N5 C7 N4 115.1(2) . . ?
N5 C7 S1 125.6(2) . . ?
N4 C7 S1 119.3(2) . . ?
C13 C8 C9 120.4(2) . . ?
C13 C8 N5 121.5(2) . . ?
C9 C8 N5 118.0(3) . . ?
C8 C9 C10 119.2(3) . . ?
C8 C9 H9 120.4 . . ?
C10 C9 H9 120.4 . . ?
C11 C10 C9 120.7(3) . . ?
C11 C10 H10 119.6 . . ?
C9 C10 H10 119.6 . . ?
C10 C11 C12 119.6(3) . . ?
C10 C11 H11 120.2 . . ?
C12 C11 H11 120.2 . . ?
C13 C12 C11 120.3(3) . . ?
C13 C12 H12 119.8 . . ?
C11 C12 H12 119.8 . . ?
C8 C13 C12 119.8(3) . . ?
C8 C13 H13 120.1 . . ?
C12 C13 H13 120.1 . . ?
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 C7 1.677(3) . ?
N1 C1 1.331(3) . ?
N1 C4 1.337(3) . ?
N2 C3 1.333(3) . ?
N2 C2 1.346(3) . ?
N3 C5 1.284(3) . ?
N3 N4 1.367(3) . ?
N4 C7 1.366(3) . ?
N4 H4 0.8800 . ?
N5 C7 1.335(3) . ?
N5 C8 1.425(3) . ?
N5 H50 0.79(3) . ?
C1 C2 1.373(4) . ?
C1 H1 0.9500 . ?
C2 H2 0.9500 . ?
C3 C4 1.389(4) . ?
C3 H3 0.9500 . ?
C4 C5 1.481(4) . ?
C5 C6 1.498(4) . ?
C6 H6A 0.9800 . ?
C6 H6B 0.9800 . ?
C6 H6C 0.9800 . ?
C8 C13 1.381(4) . ?
C8 C9 1.387(4) . ?
C9 C10 1.393(4) . ?
C9 H9 0.9500 . ?
C10 C11 1.374(4) . ?
C10 H10 0.9500 . ?
C11 C12 1.389(4) . ?
C11 H11 0.9500 . ?
C12 C13 1.386(4) . ?
C12 H12 0.9500 . ?
C13 H13 0.9500 . ?
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
C5 N3 N4 C7 -174.2(2) . . . . ?
C4 N1 C1 C2 -0.3(4) . . . . ?
C3 N2 C2 C1 -0.6(4) . . . . ?
N1 C1 C2 N2 1.4(4) . . . . ?
C2 N2 C3 C4 -1.4(4) . . . . ?
C1 N1 C4 C3 -1.6(4) . . . . ?
C1 N1 C4 C5 177.1(2) . . . . ?
N2 C3 C4 N1 2.6(4) . . . . ?
N2 C3 C4 C5 -176.1(3) . . . . ?
N4 N3 C5 C4 177.0(2) . . . . ?
N4 N3 C5 C6 0.0(4) . . . . ?
N1 C4 C5 N3 -166.4(2) . . . . ?
C3 C4 C5 N3 12.3(4) . . . . ?
N1 C4 C5 C6 10.8(4) . . . . ?
C3 C4 C5 C6 -170.5(3) . . . . ?
C8 N5 C7 N4 177.5(2) . . . . ?
C8 N5 C7 S1 -4.2(4) . . . . ?
N3 N4 C7 N5 -7.5(3) . . . . ?
N3 N4 C7 S1 174.06(18) . . . . ?
C7 N5 C8 C13 -50.6(4) . . . . ?
C7 N5 C8 C9 134.0(3) . . . . ?
C13 C8 C9 C10 -0.2(4) . . . . ?
N5 C8 C9 C10 175.2(2) . . . . ?
C8 C9 C10 C11 0.0(4) . . . . ?
C9 C10 C11 C12 0.9(4) . . . . ?
C10 C11 C12 C13 -1.7(4) . . . . ?
C9 C8 C13 C12 -0.5(4) . . . . ?
N5 C8 C13 C12 -175.8(2) . . . . ?
C11 C12 C13 C8 1.5(4) . . . . ?
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 30660823
