# Electronic Supplementary Material (ESI) for New Journal of Chemistry.
# This journal is © The Royal Society of Chemistry 2014

#######################################################################
#
#                 Cambridge Crystallographic Data Centre
#                                CCDC 
# 
#######################################################################
# 
#  This CIF contains data from an original supplementary publication
#  deposited with the CCDC, and may include chemical, crystal,
#  experimental, refinement, atomic coordinates,
#  anisotropic displacement parameters and molecular geometry data,
#  as required by the journal to which it was submitted.
#
#  This CIF is provided on the understanding that it is used for bona
#  fide research purposes only. It may contain copyright material
#  of the CCDC or of third parties, and may not be copied or further
#  disseminated in any form, whether machine-readable or not,
#  except for the purpose of generating routine backup copies
#  on your local computer system.
# 
#  For further information on the CCDC, data deposition and
#  data retrieval see:
#                         www.ccdc.cam.ac.uk
#
#  Bona fide researchers may freely download Mercury and enCIFer
#  from this site to visualise CIF-encoded structures and 
#  to carry out CIF format checking respectively.
#
data_test_0

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C20 H18 Au2 Fe N6 O4'
_chemical_formula_weight         856.19

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'
Fe Fe 0.3463 0.8444 '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'

_symmetry_cell_setting           Orthorhombic
_symmetry_space_group_name_H-M   Fdd2

loop_
_symmetry_equiv_pos_as_xyz
" 'x, y, z' "
" '-x, -y, z' "
" 'x+1/4, -y+1/4, z+1/4' "
" '-x+1/4, y+1/4, z+1/4' "
" 'x, y+1/2, z+1/2' "
" '-x, -y+1/2, z+1/2' "
" 'x+1/4, -y+3/4, z+3/4' "
" '-x+1/4, y+3/4, z+3/4' "
" 'x+1/2, y, z+1/2' "
" '-x+1/2, -y, z+1/2' "
" 'x+3/4, -y+1/4, z+3/4' "
" '-x+3/4, y+1/4, z+3/4' "
" 'x+1/2, y+1/2, z' "
" '-x+1/2, -y+1/2, z' "
" 'x+3/4, -y+3/4, z+1/4' "
" '-x+3/4, y+3/4, z+1/4' "

_cell_length_a                   15.4367(7)
_cell_length_b                   46.264(2)
_cell_length_c                   14.2833(6)
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_volume                     10200.5(8)
_cell_formula_units_Z            16
_cell_measurement_temperature    298(2)
_cell_measurement_reflns_used    5882
_cell_measurement_theta_min      2.35
_cell_measurement_theta_max      30.06

_exptl_crystal_description       Orthorhombic
_exptl_crystal_colour            yellow
_exptl_crystal_size_max          0.25
_exptl_crystal_size_mid          0.23
_exptl_crystal_size_min          0.20
_exptl_crystal_density_meas      'not measured'
_exptl_crystal_density_diffrn    2.230
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             6336
_exptl_absorpt_coefficient_mu    12.074
_exptl_absorpt_correction_type   empirical
_exptl_absorpt_correction_T_min  0.1522
_exptl_absorpt_correction_T_max  0.1962
_exptl_absorpt_process_details   'SADABS; Sheldrick 1996'

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      298(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  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean 8.333
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        0
_diffrn_reflns_number            18621
_diffrn_reflns_av_R_equivalents  0.0264
_diffrn_reflns_av_sigmaI/netI    0.0412
_diffrn_reflns_limit_h_min       -22
_diffrn_reflns_limit_h_max       17
_diffrn_reflns_limit_k_min       -66
_diffrn_reflns_limit_k_max       59
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_theta_min         1.76
_diffrn_reflns_theta_max         30.86
_reflns_number_total             7406
_reflns_number_gt                5924
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'Bruker SMART'
_computing_cell_refinement       'Bruker SMART'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'

_refine_special_details          
; 
 Refinement of F² against ALL reflections.  The weighted R-factor wR and 
" goodness of fit S are based on F², conventional R-factors R are based "
" on F, with F set to zero for negative F². The threshold expression of "
 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is 
 not relevant to the choice of reflections for refinement.  R-factors based 
" on F² 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/[σ²(Fo²)+(0.0180P)²+0.0000P] where P=(Fo²+2Fc²)/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_abs_structure_details 
" 'Flack H D (1983), Acta Cryst. A39, 876-881' "
_refine_ls_abs_structure_Flack   0.005(7)
_refine_ls_number_reflns         7406
_refine_ls_number_parameters     301
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0432
_refine_ls_R_factor_gt           0.0300
_refine_ls_wR_factor_ref         0.0591
_refine_ls_wR_factor_gt          0.0561
_refine_ls_goodness_of_fit_ref   0.992
_refine_ls_restrained_S_all      0.992
_refine_ls_shift/su_max          0.003
_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
Fe1 Fe 0.73300(4) 0.466733(13) 0.47903(8) 0.02244(12) Uani 1 1 d . . .
Au1 Au 0.482427(15) 0.466882(4) 0.728135(12) 0.03844(8) Uani 1 1 d . . .
Au2 Au 0.977268(13) 0.467412(4) 0.737656(11) 0.03488(7) Uani 1 1 d . . .
C1 C 0.8877(4) 0.46771(12) 0.3216(4) 0.0347(14) Uani 1 1 d . . .
C2 C 0.5765(4) 0.46245(12) 0.3235(4) 0.0395(15) Uani 1 1 d . . .
C3 C 0.5776(4) 0.46481(11) 0.6353(5) 0.0384(15) Uani 1 1 d . . .
C4 C 0.8796(4) 0.47128(12) 0.6470(4) 0.0357(14) Uani 1 1 d . . .
C5 C 0.7588(4) 0.40617(13) 0.5710(4) 0.0354(13) Uani 1 1 d . . .
H5 H 0.7476 0.4172 0.6241 0.042 Uiso 1 1 calc R . .
C6 C 0.7772(4) 0.37725(12) 0.5838(4) 0.0384(13) Uani 1 1 d . . .
C7 C 0.7958(4) 0.36083(11) 0.5067(4) 0.0483(15) Uani 1 1 d . . .
H7 H 0.8086 0.3413 0.5122 0.058 Uiso 1 1 calc R . .
C8 C 0.7950(5) 0.37445(13) 0.4197(4) 0.0504(16) Uani 1 1 d . . .
H8 H 0.8072 0.3640 0.3657 0.060 Uiso 1 1 calc R . .
C9 C 0.7760(4) 0.40348(14) 0.4139(4) 0.0469(16) Uani 1 1 d . . .
H9 H 0.7774 0.4123 0.3555 0.056 Uiso 1 1 calc R . .
C10 C 0.7263(4) 0.52428(12) 0.3713(4) 0.0432(14) Uani 1 1 d . . .
H10 H 0.7305 0.5112 0.3220 0.052 Uiso 1 1 calc R . .
C11 C 0.7299(4) 0.55367(12) 0.3520(4) 0.0466(15) Uani 1 1 d . . .
H11 H 0.7344 0.5601 0.2905 0.056 Uiso 1 1 calc R . .
C12 C 0.7269(4) 0.57305(13) 0.4241(4) 0.0441(14) Uani 1 1 d . . .
H12 H 0.7314 0.5928 0.4128 0.053 Uiso 1 1 calc R . .
C13 C 0.7169(4) 0.56270(12) 0.5139(3) 0.0408(13) Uani 1 1 d . . .
C14 C 0.7125(3) 0.53375(11) 0.5293(4) 0.0373(12) Uani 1 1 d . . .
H14 H 0.7061 0.5272 0.5904 0.045 Uiso 1 1 calc R . .
C15 C 0.7781(4) 0.36476(14) 0.6798(4) 0.0452(14) Uani 1 1 d . . .
C16 C 0.7906(5) 0.32196(14) 0.7687(4) 0.0611(19) Uani 1 1 d . . .
H16A H 0.7355 0.3242 0.8006 0.073 Uiso 1 1 calc R . .
H16B H 0.8358 0.3299 0.8081 0.073 Uiso 1 1 calc R . .
C17 C 0.8078(4) 0.29099(12) 0.7489(5) 0.0571(17) Uani 1 1 d . . .
H17A H 0.7583 0.2826 0.7186 0.086 Uiso 1 1 calc R . .
H17B H 0.8189 0.2810 0.8065 0.086 Uiso 1 1 calc R . .
H17C H 0.8574 0.2894 0.7087 0.086 Uiso 1 1 calc R . .
C18 C 0.7114(5) 0.58269(14) 0.5973(5) 0.063(2) Uani 1 1 d . . .
C19 C 0.6950(6) 0.63338(18) 0.6409(6) 0.090(3) Uani 1 1 d . . .
H19A H 0.6591 0.6490 0.6171 0.108 Uiso 1 1 calc R . .
H19B H 0.6693 0.6259 0.6980 0.108 Uiso 1 1 calc R . .
C20 C 0.7804(7) 0.6429(2) 0.6568(7) 0.135(5) Uani 1 1 d . . .
H20A H 0.8156 0.6269 0.6757 0.203 Uiso 1 1 calc R . .
H20B H 0.7803 0.6573 0.7053 0.203 Uiso 1 1 calc R . .
H20C H 0.8033 0.6511 0.6003 0.203 Uiso 1 1 calc R . .
N1 N 0.8347(3) 0.46805(10) 0.3764(3) 0.0384(13) Uani 1 1 d . . .
N2 N 0.6346(3) 0.46041(10) 0.3720(4) 0.0403(12) Uani 1 1 d . . .
N3 N 0.6332(3) 0.46431(10) 0.5820(4) 0.0391(13) Uani 1 1 d . . .
N4 N 0.8261(3) 0.47237(11) 0.5914(3) 0.0333(11) Uani 1 1 d . . .
N5 N 0.7558(2) 0.41943(8) 0.4886(3) 0.0315(8) Uani 1 1 d . . .
N6 N 0.7168(3) 0.51405(9) 0.4590(3) 0.0353(10) Uani 1 1 d . . .
O1 O 0.7674(4) 0.37887(9) 0.7499(3) 0.0766(16) Uani 1 1 d . . .
O2 O 0.7887(3) 0.33659(8) 0.6795(3) 0.0535(11) Uani 1 1 d . . .
O3 O 0.7136(5) 0.57535(11) 0.6765(3) 0.104(2) Uani 1 1 d . . .
O4 O 0.7050(5) 0.60964(11) 0.5684(4) 0.094(2) Uani 1 1 d . . .


_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
Fe1 N3 2.133(5) . ?
Fe1 N1 2.148(5) . ?
Fe1 N4 2.170(5) . ?
Fe1 N2 2.175(5) . ?
Fe1 N5 2.221(4) . ?
Fe1 N6 2.222(4) . ?
Au1 C1 1.980(6) 9_455 ?
Au1 C3 1.981(6) . ?
Au1 Au1 3.1120(4) 2_665 ?
Au2 C2 1.975(6) 9 ?
Au2 C4 1.995(6) . ?
Au2 Au2 3.0959(4) 2_765 ?
C1 N1 1.133(6) . ?
C1 Au1 1.980(6) 9_554 ?
C2 N2 1.137(7) . ?
C2 Au2 1.975(6) 9_454 ?
C3 N3 1.148(7) . ?
C4 N4 1.147(6) . ?
C5 N5 1.328(7) . ?
C5 C6 1.380(8) . ?
C5 H5 0.9300 . ?
C6 C7 1.368(7) . ?
C6 C15 1.488(7) . ?
C7 C8 1.394(8) . ?
C7 H7 0.9300 . ?
C8 C9 1.377(8) . ?
C8 H8 0.9300 . ?
C9 N5 1.335(7) . ?
C9 H9 0.9300 . ?
C10 N6 1.346(6) . ?
C10 C11 1.389(8) . ?
C10 H10 0.9300 . ?
C11 C12 1.366(8) . ?
C11 H11 0.9300 . ?
C12 C13 1.378(7) . ?
C12 H12 0.9300 . ?
C13 C14 1.359(7) . ?
C13 C18 1.511(8) . ?
C14 N6 1.358(6) . ?
C14 H14 0.9300 . ?
C15 O1 1.207(6) . ?
C15 O2 1.314(7) . ?
C16 O2 1.443(6) . ?
C16 C17 1.485(8) . ?
C16 H16A 0.9700 . ?
C16 H16B 0.9700 . ?
C17 H17A 0.9600 . ?
C17 H17B 0.9600 . ?
C17 H17C 0.9600 . ?
C18 O3 1.182(7) . ?
C18 O4 1.317(8) . ?
C19 C20 1.409(11) . ?
C19 O4 1.517(8) . ?
C19 H19A 0.9700 . ?
C19 H19B 0.9700 . ?
C20 H20A 0.9600 . ?
C20 H20B 0.9600 . ?
C20 H20C 0.9600 . ?

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 Fe1 N1 178.47(19) . . ?
N3 Fe1 N4 88.5(2) . . ?
N1 Fe1 N4 90.99(15) . . ?
N3 Fe1 N2 88.50(16) . . ?
N1 Fe1 N2 91.95(19) . . ?
N4 Fe1 N2 176.96(18) . . ?
N3 Fe1 N5 91.14(17) . . ?
N1 Fe1 N5 87.39(17) . . ?
N4 Fe1 N5 88.15(17) . . ?
N2 Fe1 N5 91.23(17) . . ?
N3 Fe1 N6 93.42(17) . . ?
N1 Fe1 N6 88.05(16) . . ?
N4 Fe1 N6 92.95(16) . . ?
N2 Fe1 N6 87.91(16) . . ?
N5 Fe1 N6 175.33(17) . . ?
C1 Au1 C3 178.3(2) 9_455 . ?
C1 Au1 Au1 96.30(16) 9_455 2_665 ?
C3 Au1 Au1 85.32(16) . 2_665 ?
C2 Au2 C4 177.5(2) 9 . ?
C2 Au2 Au2 86.42(16) 9 2_765 ?
C4 Au2 Au2 94.81(16) . 2_765 ?
N1 C1 Au1 178.6(6) . 9_554 ?
N2 C2 Au2 177.8(6) . 9_454 ?
N3 C3 Au1 178.3(5) . . ?
N4 C4 Au2 175.8(5) . . ?
N5 C5 C6 124.9(5) . . ?
N5 C5 H5 117.6 . . ?
C6 C5 H5 117.6 . . ?
C7 C6 C5 118.4(5) . . ?
C7 C6 C15 121.6(5) . . ?
C5 C6 C15 120.0(5) . . ?
C6 C7 C8 117.7(5) . . ?
C6 C7 H7 121.2 . . ?
C8 C7 H7 121.2 . . ?
C9 C8 C7 119.8(5) . . ?
C9 C8 H8 120.1 . . ?
C7 C8 H8 120.1 . . ?
N5 C9 C8 122.8(5) . . ?
N5 C9 H9 118.6 . . ?
C8 C9 H9 118.6 . . ?
N6 C10 C11 122.2(5) . . ?
N6 C10 H10 118.9 . . ?
C11 C10 H10 118.9 . . ?
C12 C11 C10 119.4(5) . . ?
C12 C11 H11 120.3 . . ?
C10 C11 H11 120.3 . . ?
C11 C12 C13 118.5(5) . . ?
C11 C12 H12 120.7 . . ?
C13 C12 H12 120.7 . . ?
C14 C13 C12 119.9(5) . . ?
C14 C13 C18 118.2(5) . . ?
C12 C13 C18 121.9(5) . . ?
N6 C14 C13 122.6(5) . . ?
N6 C14 H14 118.7 . . ?
C13 C14 H14 118.7 . . ?
O1 C15 O2 123.8(5) . . ?
O1 C15 C6 123.6(6) . . ?
O2 C15 C6 112.6(5) . . ?
O2 C16 C17 106.7(5) . . ?
O2 C16 H16A 110.4 . . ?
C17 C16 H16A 110.4 . . ?
O2 C16 H16B 110.4 . . ?
C17 C16 H16B 110.4 . . ?
H16A C16 H16B 108.6 . . ?
C16 C17 H17A 109.5 . . ?
C16 C17 H17B 109.5 . . ?
H17A C17 H17B 109.5 . . ?
C16 C17 H17C 109.5 . . ?
H17A C17 H17C 109.5 . . ?
H17B C17 H17C 109.5 . . ?
O3 C18 O4 125.1(6) . . ?
O3 C18 C13 125.3(6) . . ?
O4 C18 C13 109.7(6) . . ?
C20 C19 O4 104.0(8) . . ?
C20 C19 H19A 111.0 . . ?
O4 C19 H19A 111.0 . . ?
C20 C19 H19B 111.0 . . ?
O4 C19 H19B 111.0 . . ?
H19A C19 H19B 109.0 . . ?
C19 C20 H20A 109.5 . . ?
C19 C20 H20B 109.5 . . ?
H20A C20 H20B 109.5 . . ?
C19 C20 H20C 109.5 . . ?
H20A C20 H20C 109.5 . . ?
H20B C20 H20C 109.5 . . ?
C1 N1 Fe1 177.5(5) . . ?
C2 N2 Fe1 165.4(5) . . ?
C3 N3 Fe1 175.3(5) . . ?
C4 N4 Fe1 169.7(5) . . ?
C5 N5 C9 116.4(4) . . ?
C5 N5 Fe1 121.0(4) . . ?
C9 N5 Fe1 122.2(4) . . ?
C10 N6 C14 117.2(5) . . ?
C10 N6 Fe1 117.0(4) . . ?
C14 N6 Fe1 124.8(3) . . ?
C15 O2 C16 117.7(4) . . ?
C18 O4 C19 118.6(6) . . ?

_diffrn_measured_fraction_theta_max 0.948
_diffrn_reflns_theta_full        25.00
_diffrn_measured_fraction_theta_full 1.000
_refine_diff_density_max         0.817
_refine_diff_density_min         -1.067
_refine_diff_density_rms         0.125
_database_code_depnum_ccdc_archive 'CCDC 975916'
