#------------------------------------------------------------------------------
#$Date: 2016-03-25 13:38:46 +0200 (Fri, 25 Mar 2016) $
#$Revision: 179855 $
#$URL: svn://www.crystallography.net/cod/cif/7/01/51/7015178.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_7015178
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_sum            'C14 H14 Au F5 N2 O S'
_chemical_formula_weight         550.30
_chemical_melting_point          '100-106 ^o^C'
_chemical_name_common            work
_chemical_name_systematic
;
?
;
_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   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                90.00
_cell_angle_beta                 114.25(3)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   6.7762(14)
_cell_length_b                   17.691(4)
_cell_length_c                   15.393(3)
_cell_measurement_reflns_used    3190
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      25.635
_cell_measurement_theta_min      2.3025
_cell_volume                     1682.5(7)
_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 0.993
_diffrn_measured_fraction_theta_max 0.993
_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  0.0340
_diffrn_reflns_av_sigmaI/netI    0.0407
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_k_max       21
_diffrn_reflns_limit_k_min       -21
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            9242
_diffrn_reflns_theta_full        25.72
_diffrn_reflns_theta_max         25.72
_diffrn_reflns_theta_min         1.85
_exptl_absorpt_coefficient_mu    8.922
_exptl_absorpt_correction_T_max  0.7756
_exptl_absorpt_correction_T_min  0.2559
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS (Sheldrick, 1997)'
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    2.172
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       needle
_exptl_crystal_F_000             1040
_exptl_crystal_size_max          0.21
_exptl_crystal_size_mid          0.05
_exptl_crystal_size_min          0.03
_refine_diff_density_max         1.386
_refine_diff_density_min         -0.594
_refine_diff_density_rms         0.156
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.972
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     221
_refine_ls_number_reflns         3191
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.972
_refine_ls_R_factor_all          0.0370
_refine_ls_R_factor_gt           0.0278
_refine_ls_shift/su_max          0.041
_refine_ls_shift/su_mean         0.001
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0337P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0585
_refine_ls_wR_factor_ref         0.0620
_reflns_number_gt                2708
_reflns_number_total             3191
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            c0dt01312a.txt
_cod_data_source_block           3
_cod_original_cell_volume        1682.6(6)
_cod_original_sg_symbol_H-M      P21/c
_cod_database_code               7015178
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
Au1 Au 0.11109(3) 0.720413(10) 0.716473(13) 0.01600(8) Uani 1 1 d . . .
S1 S 0.2226(2) 0.87754(7) 0.85484(9) 0.0182(3) Uani 1 1 d . . .
O1 O 0.4634(7) 0.5805(2) 0.9368(3) 0.0308(10) Uani 1 1 d . . .
N1 N 0.3984(7) 0.7978(2) 1.0056(3) 0.0148(9) Uani 1 1 d . . .
C1 C 0.6307(12) 0.4874(4) 0.8795(5) 0.0477(19) Uani 1 1 d . . .
H3 H 0.6349 0.4347 0.8998 0.072 Uiso 1 1 calc R . .
H2 H 0.7639 0.5131 0.9215 0.072 Uiso 1 1 calc R . .
H1 H 0.6181 0.4889 0.8138 0.072 Uiso 1 1 calc R . .
N2 N 0.2596(7) 0.7274(2) 0.8607(3) 0.0184(10) Uani 1 1 d . . .
H14 H 0.3008 0.6848 0.8926 0.022 Uiso 1 1 calc R . .
C2 C 0.4382(10) 0.5266(3) 0.8849(4) 0.0289(14) Uani 1 1 d . . .
C3 C 0.2205(12) 0.4966(4) 0.8248(5) 0.054(2) Uani 1 1 d . . .
H4 H 0.1102 0.5280 0.8330 0.081 Uiso 1 1 calc R . .
H6 H 0.2086 0.4446 0.8439 0.081 Uiso 1 1 calc R . .
H5 H 0.1987 0.4974 0.7578 0.081 Uiso 1 1 calc R . .
C11 C -0.0339(8) 0.7112(3) 0.5744(3) 0.0145(11) Uani 1 1 d . . .
F12 F -0.0481(5) 0.57839(15) 0.58294(19) 0.0216(7) Uani 1 1 d . . .
C12 C -0.0925(8) 0.6428(3) 0.5295(4) 0.0157(11) Uani 1 1 d . . .
F13 F -0.2455(5) 0.56381(17) 0.3928(2) 0.0264(7) Uani 1 1 d . . .
C13 C -0.1938(8) 0.6331(3) 0.4325(3) 0.0188(11) Uani 1 1 d . . .
F14 F -0.3406(5) 0.68806(18) 0.2794(2) 0.0292(7) Uani 1 1 d . . .
C14 C -0.2425(9) 0.6957(3) 0.3748(4) 0.0217(12) Uani 1 1 d . . .
F15 F -0.2318(5) 0.82815(18) 0.3585(2) 0.0312(8) Uani 1 1 d . . .
C15 C -0.1881(9) 0.7664(3) 0.4147(4) 0.0217(12) Uani 1 1 d . . .
F16 F -0.0340(5) 0.84391(16) 0.5484(2) 0.0265(7) Uani 1 1 d . . .
C16 C -0.0855(8) 0.7727(3) 0.5129(4) 0.0175(11) Uani 1 1 d . . .
C21 C 0.2986(8) 0.7893(3) 0.9095(4) 0.0173(11) Uani 1 1 d . . .
C22 C 0.3246(8) 0.9221(3) 0.9657(4) 0.0201(11) Uani 1 1 d . . .
H7 H 0.3186 0.9751 0.9742 0.024 Uiso 1 1 calc R . .
C23 C 0.4122(8) 0.8730(3) 1.0372(4) 0.0182(11) Uani 1 1 d . . .
C24 C 0.4729(9) 0.7327(3) 1.0698(4) 0.0198(12) Uani 1 1 d . . .
H10 H 0.3566 0.7158 1.0874 0.030 Uiso 1 1 calc R . .
H8 H 0.5992 0.7472 1.1273 0.030 Uiso 1 1 calc R . .
H9 H 0.5127 0.6915 1.0375 0.030 Uiso 1 1 calc R . .
C25 C 0.5172(9) 0.8904(3) 1.1412(3) 0.0232(12) Uani 1 1 d . . .
H11 H 0.5189 0.9452 1.1506 0.035 Uiso 1 1 calc R . .
H13 H 0.6660 0.8712 1.1679 0.035 Uiso 1 1 calc R . .
H12 H 0.4356 0.8661 1.1734 0.035 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'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
F F 0.0171 0.0103 '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'
Au Au -2.0133 8.8022 '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
C11 Au1 N2 178.78(17) . . ?
C22 S1 C21 90.7(2) . . ?
C21 N1 C23 114.5(4) . . ?
C21 N1 C24 121.7(4) . . ?
C23 N1 C24 123.7(4) . . ?
C2 C1 H3 109.5 . . ?
C2 C1 H2 109.5 . . ?
H3 C1 H2 109.5 . . ?
C2 C1 H1 109.5 . . ?
H3 C1 H1 109.5 . . ?
H2 C1 H1 109.5 . . ?
C21 N2 Au1 125.3(3) . . ?
C21 N2 H14 117.3 . . ?
Au1 N2 H14 117.3 . . ?
O1 C2 C3 121.9(6) . . ?
O1 C2 C1 120.5(6) . . ?
C3 C2 C1 117.6(6) . . ?
C2 C3 H4 109.5 . . ?
C2 C3 H6 109.5 . . ?
H4 C3 H6 109.5 . . ?
C2 C3 H5 109.5 . . ?
H4 C3 H5 109.5 . . ?
H6 C3 H5 109.5 . . ?
C12 C11 C16 114.1(5) . . ?
C12 C11 Au1 122.3(4) . . ?
C16 C11 Au1 123.6(4) . . ?
F12 C12 C11 119.1(4) . . ?
F12 C12 C13 116.1(4) . . ?
C11 C12 C13 124.8(5) . . ?
F13 C13 C14 119.4(4) . . ?
F13 C13 C12 121.7(4) . . ?
C14 C13 C12 118.9(5) . . ?
F14 C14 C13 120.3(5) . . ?
F14 C14 C15 120.0(5) . . ?
C13 C14 C15 119.7(5) . . ?
F15 C15 C14 120.1(5) . . ?
F15 C15 C16 121.0(5) . . ?
C14 C15 C16 118.9(5) . . ?
F16 C16 C15 116.4(4) . . ?
F16 C16 C11 120.0(5) . . ?
C15 C16 C11 123.6(5) . . ?
N2 C21 N1 128.2(5) . . ?
N2 C21 S1 121.8(4) . . ?
N1 C21 S1 109.9(4) . . ?
C23 C22 S1 112.1(4) . . ?
C23 C22 H7 123.9 . . ?
S1 C22 H7 123.9 . . ?
C22 C23 N1 112.7(4) . . ?
C22 C23 C25 127.3(5) . . ?
N1 C23 C25 120.0(4) . . ?
N1 C24 H10 109.5 . . ?
N1 C24 H8 109.5 . . ?
H10 C24 H8 109.5 . . ?
N1 C24 H9 109.5 . . ?
H10 C24 H9 109.5 . . ?
H8 C24 H9 109.5 . . ?
C23 C25 H11 109.5 . . ?
C23 C25 H13 109.5 . . ?
H11 C25 H13 109.5 . . ?
C23 C25 H12 109.5 . . ?
H11 C25 H12 109.5 . . ?
H13 C25 H12 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
Au1 C11 2.002(5) . ?
Au1 N2 2.031(4) . ?
S1 C22 1.744(5) . ?
S1 C21 1.748(5) . ?
O1 C2 1.211(6) . ?
N1 C21 1.359(6) . ?
N1 C23 1.406(6) . ?
N1 C24 1.466(6) . ?
C1 C2 1.509(9) . ?
C1 H3 0.9800 . ?
C1 H2 0.9800 . ?
C1 H1 0.9800 . ?
N2 C21 1.292(6) . ?
N2 H14 0.8800 . ?
C2 C3 1.481(9) . ?
C3 H4 0.9800 . ?
C3 H6 0.9800 . ?
C3 H5 0.9800 . ?
C11 C12 1.370(7) . ?
C11 C16 1.390(7) . ?
F12 C12 1.364(5) . ?
C12 C13 1.374(7) . ?
F13 C13 1.350(6) . ?
C13 C14 1.372(7) . ?
F14 C14 1.347(6) . ?
C14 C15 1.376(8) . ?
F15 C15 1.349(6) . ?
C15 C16 1.385(8) . ?
F16 C16 1.360(5) . ?
C22 C23 1.334(7) . ?
C22 H7 0.9500 . ?
C23 C25 1.493(7) . ?
C24 H10 0.9800 . ?
C24 H8 0.9800 . ?
C24 H9 0.9800 . ?
C25 H11 0.9800 . ?
C25 H13 0.9800 . ?
C25 H12 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
C16 C11 C12 F12 179.5(4) . . . . ?
Au1 C11 C12 F12 -0.9(7) . . . . ?
C16 C11 C12 C13 -0.1(8) . . . . ?
Au1 C11 C12 C13 179.4(4) . . . . ?
F12 C12 C13 F13 -0.2(7) . . . . ?
C11 C12 C13 F13 179.4(5) . . . . ?
F12 C12 C13 C14 -179.9(5) . . . . ?
C11 C12 C13 C14 -0.3(8) . . . . ?
F13 C13 C14 F14 -0.1(8) . . . . ?
C12 C13 C14 F14 179.6(5) . . . . ?
F13 C13 C14 C15 -179.2(5) . . . . ?
C12 C13 C14 C15 0.5(8) . . . . ?
F14 C14 C15 F15 -0.3(8) . . . . ?
C13 C14 C15 F15 178.8(5) . . . . ?
F14 C14 C15 C16 -179.4(5) . . . . ?
C13 C14 C15 C16 -0.3(8) . . . . ?
F15 C15 C16 F16 0.4(7) . . . . ?
C14 C15 C16 F16 179.5(5) . . . . ?
F15 C15 C16 C11 -179.2(5) . . . . ?
C14 C15 C16 C11 -0.1(8) . . . . ?
C12 C11 C16 F16 -179.3(4) . . . . ?
Au1 C11 C16 F16 1.2(7) . . . . ?
C12 C11 C16 C15 0.3(8) . . . . ?
Au1 C11 C16 C15 -179.2(4) . . . . ?
Au1 N2 C21 N1 -179.4(4) . . . . ?
Au1 N2 C21 S1 0.7(7) . . . . ?
C23 N1 C21 N2 -178.7(5) . . . . ?
C24 N1 C21 N2 -2.0(8) . . . . ?
C23 N1 C21 S1 1.2(5) . . . . ?
C24 N1 C21 S1 177.9(4) . . . . ?
C22 S1 C21 N2 178.6(5) . . . . ?
C22 S1 C21 N1 -1.3(4) . . . . ?
C21 S1 C22 C23 1.1(4) . . . . ?
S1 C22 C23 N1 -0.6(6) . . . . ?
S1 C22 C23 C25 179.2(4) . . . . ?
C21 N1 C23 C22 -0.4(7) . . . . ?
C24 N1 C23 C22 -177.0(5) . . . . ?
C21 N1 C23 C25 179.7(5) . . . . ?
C24 N1 C23 C25 3.1(8) . . . . ?
