#------------------------------------------------------------------------------
#$Date: 2016-03-25 13:38:46 +0200 (Fri, 25 Mar 2016) $
#$Revision: 179855 $
#$URL: svn://www.crystallography.net/cod/cif/7/01/51/7015175.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_7015175
loop_
_publ_author_name
'Coetzee, Jacorien'
'Cronje, Stephanie'
'Dobrzańska, Liliana'
'Raubenheimer, Helgard G.'
'Jooné, Gisela'
'Nell, Margo J.'
'Hoppe, Heinrich C.'
_publ_section_title
;
 Novel N-heterocyclic ylideneamine gold(I) complexes: synthesis,
 characterisation and screening for antitumour and antimalarial
 activity.
;
_journal_issue                   7
_journal_name_full
'Dalton transactions (Cambridge, England : 2003)'
_journal_page_first              1471
_journal_page_last               1483
_journal_paper_doi               10.1039/c0dt01312a
_journal_volume                  40
_journal_year                    2011
_chemical_formula_moiety         'C5 H8 N2 S'
_chemical_formula_sum            'C5 H8 N2 S'
_chemical_formula_weight         128.19
_chemical_melting_point          '46-48 ^o^C'
_chemical_name_common            work
_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                108.286(3)
_cell_angle_beta                 101.346(3)
_cell_angle_gamma                91.652(3)
_cell_formula_units_Z            8
_cell_length_a                   6.9494(14)
_cell_length_b                   13.498(3)
_cell_length_c                   14.301(3)
_cell_measurement_reflns_used    1620
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      25.652
_cell_measurement_theta_min      2.5515
_cell_volume                     1242.9(5)
_computing_cell_refinement       'SAINT (Bruker, 2003)'
_computing_data_collection       'SMART (Bruker, 2003)'
_computing_data_reduction        SAINT
_computing_molecular_graphics    'X-Seed (Barbour, 2003)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      100(2)
_diffrn_measured_fraction_theta_full 0.980
_diffrn_measured_fraction_theta_max 0.976
_diffrn_measurement_device_type  'Bruker APEX CCD area-detector'
_diffrn_measurement_method       ω
_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  0.0467
_diffrn_reflns_av_sigmaI/netI    0.0968
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_l_max       7
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            6852
_diffrn_reflns_theta_full        25.50
_diffrn_reflns_theta_max         25.69
_diffrn_reflns_theta_min         1.60
_exptl_absorpt_coefficient_mu    0.408
_exptl_absorpt_correction_T_max  0.9799
_exptl_absorpt_correction_T_min  0.8874
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS (Sheldrick, 1997)'
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.370
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             544
_exptl_crystal_size_max          0.30
_exptl_crystal_size_mid          0.10
_exptl_crystal_size_min          0.05
_refine_diff_density_max         0.433
_refine_diff_density_min         -0.274
_refine_diff_density_rms         0.067
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.880
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     301
_refine_ls_number_reflns         4625
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.880
_refine_ls_R_factor_all          0.0774
_refine_ls_R_factor_gt           0.0457
_refine_ls_shift/su_max          0.002
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0265P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0807
_refine_ls_wR_factor_ref         0.0886
_reflns_number_gt                3101
_reflns_number_total             4625
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            c0dt01312a.txt
_cod_data_source_block           II
_cod_original_cell_volume        1242.9(4)
_cod_original_sg_symbol_H-M      P-1
_cod_database_code               7015175
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 0.28681(11) -0.12126(6) 1.05834(6) 0.01761(19) Uani 1 1 d . . .
N1 N 0.2697(3) 0.05823(17) 1.03296(17) 0.0147(5) Uani 1 1 d . . .
C1 C 0.3141(4) 0.0180(2) 1.1108(2) 0.0150(7) Uani 1 1 d . . .
S2 S 0.17573(11) 0.29950(6) 0.83201(6) 0.0205(2) Uani 1 1 d . . .
N2 N 0.3658(4) 0.07499(18) 1.20362(18) 0.0179(6) Uani 1 1 d . . .
H8 H 0.3852 0.0395 1.2368 0.022 Uiso 1 1 calc R . .
C2 C 0.2151(4) -0.0160(2) 0.9362(2) 0.0164(7) Uani 1 1 d . . .
S3 S 0.90125(11) 0.70773(6) 0.68916(6) 0.01976(19) Uani 1 1 d . . .
N3 N 0.0479(3) 0.47984(18) 0.87299(18) 0.0177(6) Uani 1 1 d . . .
C3 C 0.2173(4) -0.1143(2) 0.9369(2) 0.0180(7) Uani 1 1 d . . .
H1 H 0.1846 -0.1740 0.8777 0.022 Uiso 1 1 calc R . .
S4 S 0.32297(11) 0.18618(6) 0.56989(6) 0.02025(19) Uani 1 1 d . . .
N4 N -0.2060(3) 0.34876(19) 0.8381(2) 0.0229(6) Uani 1 1 d . . .
H16 H -0.2234 0.2885 0.8177 0.028 Uiso 1 1 calc R . .
C4 C 0.2796(4) 0.1714(2) 1.0561(2) 0.0188(7) Uani 1 1 d . . .
H2 H 0.1854 0.1999 1.0981 0.028 Uiso 1 1 calc R . .
H4 H 0.2469 0.1881 0.9933 0.028 Uiso 1 1 calc R . .
H3 H 0.4133 0.2025 1.0926 0.028 Uiso 1 1 calc R . .
N5 N 0.6854(3) 0.53424(18) 0.63639(18) 0.0192(6) Uani 1 1 d . . .
C5 C 0.1631(4) 0.0174(2) 0.8451(2) 0.0196(7) Uani 1 1 d . . .
H7 H 0.1242 -0.0447 0.7848 0.029 Uiso 1 1 calc R . .
H6 H 0.2775 0.0575 0.8395 0.029 Uiso 1 1 calc R . .
H5 H 0.0532 0.0612 0.8512 0.029 Uiso 1 1 calc R . .
N6 N 0.5072(3) 0.67740(18) 0.69110(19) 0.0199(6) Uani 1 1 d . . .
H24 H 0.5256 0.7375 0.7146 0.024 Uiso 1 1 calc R . .
C6 C -0.0250(4) 0.3771(2) 0.8469(2) 0.0170(7) Uani 1 1 d . . .
N7 N 0.6608(3) 0.11630(18) 0.58032(18) 0.0160(6) Uani 1 1 d . . .
C7 C 0.2498(4) 0.4975(2) 0.8787(2) 0.0176(7) Uani 1 1 d . . .
N8 N 0.5358(4) 0.1230(2) 0.72179(19) 0.0226(6) Uani 1 1 d . . .
H32 H 0.4438 0.1392 0.7432 0.027 Uiso 1 1 calc R . .
C8 C 0.3401(4) 0.4103(2) 0.8592(2) 0.0213(7) Uani 1 1 d . . .
H9 H 0.4770 0.4083 0.8599 0.026 Uiso 1 1 calc R . .
C9 C -0.0869(4) 0.5618(2) 0.8912(2) 0.0250(8) Uani 1 1 d . . .
H12 H -0.1741 0.5582 0.8271 0.037 Uiso 1 1 calc R . .
H11 H -0.0107 0.6306 0.9211 0.037 Uiso 1 1 calc R . .
H10 H -0.1663 0.5513 0.9374 0.037 Uiso 1 1 calc R . .
C10 C 0.3425(4) 0.6061(2) 0.9054(2) 0.0260(8) Uani 1 1 d . . .
H15 H 0.4834 0.6044 0.9054 0.039 Uiso 1 1 calc R . .
H14 H 0.3257 0.6476 0.9725 0.039 Uiso 1 1 calc R . .
H13 H 0.2795 0.6379 0.8557 0.039 Uiso 1 1 calc R . .
C11 C 0.6668(4) 0.6400(2) 0.6735(2) 0.0164(7) Uani 1 1 d . . .
C12 C 0.8735(4) 0.5066(2) 0.6240(2) 0.0197(7) Uani 1 1 d . . .
C13 C 1.0052(4) 0.5896(2) 0.6480(2) 0.0208(7) Uani 1 1 d . . .
H17 H 1.1393 0.5849 0.6434 0.025 Uiso 1 1 calc R . .
C14 C 0.5161(4) 0.4594(2) 0.6190(2) 0.0286(8) Uani 1 1 d . . .
H18 H 0.4063 0.4723 0.5710 0.043 Uiso 1 1 calc R . .
H19 H 0.4765 0.4676 0.6829 0.043 Uiso 1 1 calc R . .
H20 H 0.5517 0.3879 0.5913 0.043 Uiso 1 1 calc R . .
C15 C 0.9092(5) 0.3940(2) 0.5871(2) 0.0279(8) Uani 1 1 d . . .
H23 H 1.0465 0.3886 0.5804 0.042 Uiso 1 1 calc R . .
H22 H 0.8210 0.3594 0.5213 0.042 Uiso 1 1 calc R . .
H21 H 0.8837 0.3600 0.6354 0.042 Uiso 1 1 calc R . .
C16 C 0.5181(4) 0.1376(2) 0.6365(2) 0.0167(7) Uani 1 1 d . . .
C17 C 0.6184(4) 0.1361(2) 0.4889(2) 0.0177(7) Uani 1 1 d . . .
C18 C 0.4442(4) 0.1732(2) 0.4712(2) 0.0200(7) Uani 1 1 d . . .
H25 H 0.3923 0.1904 0.4122 0.024 Uiso 1 1 calc R . .
C19 C 0.8431(4) 0.0785(2) 0.6205(2) 0.0235(7) Uani 1 1 d . . .
H26 H 0.9226 0.1357 0.6769 0.035 Uiso 1 1 calc R . .
H28 H 0.9175 0.0539 0.5674 0.035 Uiso 1 1 calc R . .
H27 H 0.8115 0.0206 0.6442 0.035 Uiso 1 1 calc R . .
C20 C 0.7629(4) 0.1171(2) 0.4215(2) 0.0216(7) Uani 1 1 d . . .
H31 H 0.7116 0.1381 0.3624 0.032 Uiso 1 1 calc R . .
H30 H 0.7829 0.0424 0.3996 0.032 Uiso 1 1 calc R . .
H29 H 0.8889 0.1583 0.4585 0.032 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
C3 S1 C1 90.96(14) . . ?
C1 N1 C2 115.5(2) . . ?
C1 N1 C4 118.9(2) . . ?
C2 N1 C4 125.6(2) . . ?
N2 C1 N1 123.5(3) . . ?
N2 C1 S1 128.5(2) . . ?
N1 C1 S1 108.0(2) . . ?
C8 S2 C6 91.64(14) . . ?
C1 N2 H8 109.5 . . ?
C3 C2 N1 113.0(3) . . ?
C3 C2 C5 126.1(3) . . ?
N1 C2 C5 120.9(3) . . ?
C13 S3 C11 91.48(14) . . ?
C6 N3 C7 115.9(2) . . ?
C6 N3 C9 119.1(2) . . ?
C7 N3 C9 124.9(2) . . ?
C2 C3 S1 112.4(2) . . ?
C2 C3 H1 123.8 . . ?
S1 C3 H1 123.8 . . ?
C18 S4 C16 91.57(14) . . ?
C6 N4 H16 109.5 . . ?
N1 C4 H2 109.5 . . ?
N1 C4 H4 109.5 . . ?
H2 C4 H4 109.5 . . ?
N1 C4 H3 109.5 . . ?
H2 C4 H3 109.5 . . ?
H4 C4 H3 109.5 . . ?
C11 N5 C12 116.2(2) . . ?
C11 N5 C14 119.3(2) . . ?
C12 N5 C14 124.5(2) . . ?
C2 C5 H7 109.5 . . ?
C2 C5 H6 109.5 . . ?
H7 C5 H6 109.5 . . ?
C2 C5 H5 109.5 . . ?
H7 C5 H5 109.5 . . ?
H6 C5 H5 109.5 . . ?
C11 N6 H24 109.5 . . ?
N4 C6 N3 123.1(3) . . ?
N4 C6 S2 129.4(2) . . ?
N3 C6 S2 107.5(2) . . ?
C16 N7 C17 115.6(2) . . ?
C16 N7 C19 119.1(2) . . ?
C17 N7 C19 125.3(2) . . ?
C8 C7 N3 113.4(3) . . ?
C8 C7 C10 126.6(3) . . ?
N3 C7 C10 120.0(2) . . ?
C16 N8 H32 109.5 . . ?
C7 C8 S2 111.5(2) . . ?
C7 C8 H9 124.2 . . ?
S2 C8 H9 124.2 . . ?
N3 C9 H12 109.5 . . ?
N3 C9 H11 109.5 . . ?
H12 C9 H11 109.5 . . ?
N3 C9 H10 109.5 . . ?
H12 C9 H10 109.5 . . ?
H11 C9 H10 109.5 . . ?
C7 C10 H15 109.5 . . ?
C7 C10 H14 109.5 . . ?
H15 C10 H14 109.5 . . ?
C7 C10 H13 109.5 . . ?
H15 C10 H13 109.5 . . ?
H14 C10 H13 109.5 . . ?
N6 C11 N5 123.7(3) . . ?
N6 C11 S3 128.9(2) . . ?
N5 C11 S3 107.3(2) . . ?
C13 C12 N5 113.0(3) . . ?
C13 C12 C15 127.0(3) . . ?
N5 C12 C15 120.0(3) . . ?
C12 C13 S3 111.9(2) . . ?
C12 C13 H17 124.0 . . ?
S3 C13 H17 124.0 . . ?
N5 C14 H18 109.5 . . ?
N5 C14 H19 109.5 . . ?
H18 C14 H19 109.5 . . ?
N5 C14 H20 109.5 . . ?
H18 C14 H20 109.5 . . ?
H19 C14 H20 109.5 . . ?
C12 C15 H23 109.5 . . ?
C12 C15 H22 109.5 . . ?
H23 C15 H22 109.5 . . ?
C12 C15 H21 109.5 . . ?
H23 C15 H21 109.5 . . ?
H22 C15 H21 109.5 . . ?
N8 C16 N7 122.8(3) . . ?
N8 C16 S4 129.3(2) . . ?
N7 C16 S4 107.9(2) . . ?
C18 C17 N7 113.3(3) . . ?
C18 C17 C20 126.0(3) . . ?
N7 C17 C20 120.6(2) . . ?
C17 C18 S4 111.6(2) . . ?
C17 C18 H25 124.2 . . ?
S4 C18 H25 124.2 . . ?
N7 C19 H26 109.5 . . ?
N7 C19 H28 109.5 . . ?
H26 C19 H28 109.5 . . ?
N7 C19 H27 109.5 . . ?
H26 C19 H27 109.5 . . ?
H28 C19 H27 109.5 . . ?
C17 C20 H31 109.5 . . ?
C17 C20 H30 109.5 . . ?
H31 C20 H30 109.5 . . ?
C17 C20 H29 109.5 . . ?
H31 C20 H29 109.5 . . ?
H30 C20 H29 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
S1 C3 1.742(3) . ?
S1 C1 1.781(3) . ?
N1 C1 1.372(4) . ?
N1 C2 1.401(3) . ?
N1 C4 1.455(3) . ?
C1 N2 1.280(3) . ?
S2 C8 1.748(3) . ?
S2 C6 1.775(3) . ?
N2 H8 0.7700 . ?
C2 C3 1.329(4) . ?
C2 C5 1.491(4) . ?
S3 C13 1.748(3) . ?
S3 C11 1.784(3) . ?
N3 C6 1.371(4) . ?
N3 C7 1.398(4) . ?
N3 C9 1.464(3) . ?
C3 H1 0.9500 . ?
S4 C18 1.747(3) . ?
S4 C16 1.764(3) . ?
N4 C6 1.274(3) . ?
N4 H16 0.7700 . ?
C4 H2 0.9800 . ?
C4 H4 0.9800 . ?
C4 H3 0.9800 . ?
N5 C11 1.378(3) . ?
N5 C12 1.399(4) . ?
N5 C14 1.458(4) . ?
C5 H7 0.9800 . ?
C5 H6 0.9800 . ?
C5 H5 0.9800 . ?
N6 C11 1.269(3) . ?
N6 H24 0.7700 . ?
N7 C16 1.377(4) . ?
N7 C17 1.393(4) . ?
N7 C19 1.460(3) . ?
C7 C8 1.328(4) . ?
C7 C10 1.485(4) . ?
N8 C16 1.278(4) . ?
N8 H32 0.7700 . ?
C8 H9 0.9500 . ?
C9 H12 0.9800 . ?
C9 H11 0.9800 . ?
C9 H10 0.9800 . ?
C10 H15 0.9800 . ?
C10 H14 0.9800 . ?
C10 H13 0.9800 . ?
C12 C13 1.336(4) . ?
C12 C15 1.491(4) . ?
C13 H17 0.9500 . ?
C14 H18 0.9800 . ?
C14 H19 0.9800 . ?
C14 H20 0.9800 . ?
C15 H23 0.9800 . ?
C15 H22 0.9800 . ?
C15 H21 0.9800 . ?
C17 C18 1.332(4) . ?
C17 C20 1.498(4) . ?
C18 H25 0.9500 . ?
C19 H26 0.9800 . ?
C19 H28 0.9800 . ?
C19 H27 0.9800 . ?
C20 H31 0.9800 . ?
C20 H30 0.9800 . ?
C20 H29 0.9800 . ?
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
C2 N1 C1 N2 -179.7(3) . . . . ?
C4 N1 C1 N2 -0.6(4) . . . . ?
C2 N1 C1 S1 0.4(3) . . . . ?
C4 N1 C1 S1 179.59(19) . . . . ?
C3 S1 C1 N2 179.9(3) . . . . ?
C3 S1 C1 N1 -0.2(2) . . . . ?
C1 N1 C2 C3 -0.4(3) . . . . ?
C4 N1 C2 C3 -179.5(3) . . . . ?
C1 N1 C2 C5 180.0(2) . . . . ?
C4 N1 C2 C5 0.9(4) . . . . ?
N1 C2 C3 S1 0.2(3) . . . . ?
C5 C2 C3 S1 179.8(2) . . . . ?
C1 S1 C3 C2 0.0(2) . . . . ?
C7 N3 C6 N4 -179.6(3) . . . . ?
C9 N3 C6 N4 -0.5(4) . . . . ?
C7 N3 C6 S2 1.5(3) . . . . ?
C9 N3 C6 S2 -179.4(2) . . . . ?
C8 S2 C6 N4 180.0(3) . . . . ?
C8 S2 C6 N3 -1.2(2) . . . . ?
C6 N3 C7 C8 -1.1(4) . . . . ?
C9 N3 C7 C8 179.8(3) . . . . ?
C6 N3 C7 C10 179.4(3) . . . . ?
C9 N3 C7 C10 0.3(4) . . . . ?
N3 C7 C8 S2 0.1(3) . . . . ?
C10 C7 C8 S2 179.6(2) . . . . ?
C6 S2 C8 C7 0.7(2) . . . . ?
C12 N5 C11 N6 -178.3(3) . . . . ?
C14 N5 C11 N6 -2.2(4) . . . . ?
C12 N5 C11 S3 2.1(3) . . . . ?
C14 N5 C11 S3 178.2(2) . . . . ?
C13 S3 C11 N6 179.0(3) . . . . ?
C13 S3 C11 N5 -1.4(2) . . . . ?
C11 N5 C12 C13 -1.8(4) . . . . ?
C14 N5 C12 C13 -177.8(3) . . . . ?
C11 N5 C12 C15 178.2(3) . . . . ?
C14 N5 C12 C15 2.2(4) . . . . ?
N5 C12 C13 S3 0.6(3) . . . . ?
C15 C12 C13 S3 -179.4(3) . . . . ?
C11 S3 C13 C12 0.4(2) . . . . ?
C17 N7 C16 N8 179.7(3) . . . . ?
C19 N7 C16 N8 -2.0(4) . . . . ?
C17 N7 C16 S4 -0.6(3) . . . . ?
C19 N7 C16 S4 177.72(19) . . . . ?
C18 S4 C16 N8 -179.7(3) . . . . ?
C18 S4 C16 N7 0.7(2) . . . . ?
C16 N7 C17 C18 0.1(4) . . . . ?
C19 N7 C17 C18 -178.0(3) . . . . ?
C16 N7 C17 C20 179.4(2) . . . . ?
C19 N7 C17 C20 1.2(4) . . . . ?
N7 C17 C18 S4 0.4(3) . . . . ?
C20 C17 C18 S4 -178.8(2) . . . . ?
C16 S4 C18 C17 -0.6(2) . . . . ?
