# Electronic Supplementary Material (ESI) for New Journal of Chemistry.
# This journal is © The Royal Society of Chemistry and the Centre National de la Recherche Scientifique 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
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#  data retrieval see:
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#  from this site to visualise CIF-encoded structures and 
#  to carry out CIF format checking respectively.
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data_zhao59

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C33 H24 Au N2 O3 P'
_chemical_formula_weight         724.48

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'
P P 0.1023 0.0942 '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           Triclinic
_symmetry_space_group_name_H-M   P-1

loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   8.7748(18)
_cell_length_b                   9.1491(18)
_cell_length_c                   17.558(4)
_cell_angle_alpha                93.54(3)
_cell_angle_beta                 97.12(3)
_cell_angle_gamma                98.33(3)
_cell_volume                     1379.4(5)
_cell_formula_units_Z            2
_cell_measurement_temperature    173(2)
_cell_measurement_reflns_used    5743
_cell_measurement_theta_min      2.26
_cell_measurement_theta_max      27.11

_exptl_crystal_description       plate
_exptl_crystal_colour            yellow
_exptl_crystal_size_max          0.44
_exptl_crystal_size_mid          0.33
_exptl_crystal_size_min          0.06
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.744
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             708
_exptl_absorpt_coefficient_mu    5.429
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.491935
_exptl_absorpt_correction_T_max  1.0
_exptl_absorpt_process_details   /SADABS/

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      173(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  'Bruker P4'
_diffrn_measurement_method       'ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            10395
_diffrn_reflns_av_R_equivalents  0.0385
_diffrn_reflns_av_unetI/netI     0.0602
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_theta_min         2.26
_diffrn_reflns_theta_max         26.00
_reflns_number_total             5257
_reflns_number_gt                4318
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'Bruker XSCANS'
_computing_cell_refinement       'Bruker XSCANS'
_computing_data_reduction        'Bruker SHELXTL'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_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)+(0.0803P)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_number_reflns         5257
_refine_ls_number_parameters     361
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0486
_refine_ls_R_factor_gt           0.0345
_refine_ls_wR_factor_ref         0.0918
_refine_ls_wR_factor_gt          0.0854
_refine_ls_goodness_of_fit_ref   0.768
_refine_ls_restrained_S_all      0.768
_refine_ls_shift/su_max          0.002
_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
Au1 Au 0.91274(2) 0.91365(2) 0.710404(12) 0.03032(9) Uani 1 1 d . . .
P1 P 0.73083(16) 0.74374(15) 0.63557(9) 0.0279(3) Uani 1 1 d . . .
O1 O 1.9177(5) 1.4812(5) 0.8685(3) 0.0496(11) Uani 1 1 d . . .
O2 O 2.3943(6) 2.1340(6) 1.0108(3) 0.0612(13) Uani 1 1 d . . .
O3 O 2.3270(7) 2.0903(7) 1.1220(3) 0.0770(17) Uani 1 1 d . . .
N1 N 1.7227(5) 1.5640(6) 0.9253(3) 0.0421(12) Uani 1 1 d . . .
H1A H 1.7049 1.6299 0.9587 0.051 Uiso 1 1 calc R . .
N2 N 2.3178(6) 2.0611(7) 1.0530(4) 0.0488(14) Uani 1 1 d . . .
C1 C 1.0842(5) 1.0653(5) 0.7676(3) 0.0246(11) Uani 1 1 d . . .
C2 C 1.1911(7) 1.1553(6) 0.7956(3) 0.0335(13) Uani 1 1 d . . .
C3 C 1.8731(6) 1.5722(7) 0.9106(4) 0.0375(14) Uani 1 1 d . . .
C11 C 0.5433(6) 0.7003(6) 0.6694(3) 0.0292(12) Uani 1 1 d . . .
C12 C 0.4505(7) 0.5651(7) 0.6501(4) 0.0406(14) Uani 1 1 d . . .
H12A H 0.4873 0.4909 0.6223 0.049 Uiso 1 1 calc R . .
C13 C 0.3013(7) 0.5379(7) 0.6718(4) 0.0442(15) Uani 1 1 d . . .
H13A H 0.2405 0.4453 0.6605 0.053 Uiso 1 1 calc R . .
C14 C 0.2465(7) 0.6509(7) 0.7102(4) 0.0406(14) Uani 1 1 d . . .
H14A H 0.1460 0.6354 0.7230 0.049 Uiso 1 1 calc R . .
C15 C 0.3380(7) 0.7863(7) 0.7300(4) 0.0433(15) Uani 1 1 d . . .
H15A H 0.2993 0.8611 0.7564 0.052 Uiso 1 1 calc R . .
C16 C 0.4885(6) 0.8124(6) 0.7108(3) 0.0347(13) Uani 1 1 d . . .
H16A H 0.5514 0.9032 0.7252 0.042 Uiso 1 1 calc R . .
C21 C 0.7964(6) 0.5653(6) 0.6228(3) 0.0315(12) Uani 1 1 d . . .
C22 C 0.8131(7) 0.5004(6) 0.5507(4) 0.0405(14) Uani 1 1 d . . .
H22A H 0.7895 0.5475 0.5063 0.049 Uiso 1 1 calc R . .
C23 C 0.8658(8) 0.3641(7) 0.5466(5) 0.0533(18) Uani 1 1 d . . .
H23A H 0.8778 0.3202 0.4990 0.064 Uiso 1 1 calc R . .
C24 C 0.9004(8) 0.2932(8) 0.6123(5) 0.060(2) Uani 1 1 d . . .
H24A H 0.9355 0.2022 0.6086 0.072 Uiso 1 1 calc R . .
C25 C 0.8831(7) 0.3565(8) 0.6834(5) 0.0509(17) Uani 1 1 d . . .
H25A H 0.9057 0.3082 0.7276 0.061 Uiso 1 1 calc R . .
C26 C 0.8321(7) 0.4922(6) 0.6887(4) 0.0396(14) Uani 1 1 d . . .
H26A H 0.8213 0.5354 0.7367 0.047 Uiso 1 1 calc R . .
C31 C 0.6896(6) 0.8036(6) 0.5392(3) 0.0300(12) Uani 1 1 d . . .
C32 C 0.8089(8) 0.8663(9) 0.5032(4) 0.0575(19) Uani 1 1 d . . .
H32A H 0.9096 0.8823 0.5292 0.069 Uiso 1 1 calc R . .
C33 C 0.7825(9) 0.9064(9) 0.4288(4) 0.065(2) Uani 1 1 d . . .
H33A H 0.8658 0.9483 0.4052 0.078 Uiso 1 1 calc R . .
C34 C 0.6345(9) 0.8854(8) 0.3888(4) 0.0516(17) Uani 1 1 d . . .
H34A H 0.6173 0.9109 0.3383 0.062 Uiso 1 1 calc R . .
C35 C 0.5144(8) 0.8266(8) 0.4248(4) 0.0552(18) Uani 1 1 d . . .
H35A H 0.4136 0.8138 0.3991 0.066 Uiso 1 1 calc R . .
C36 C 0.5399(7) 0.7848(7) 0.5002(4) 0.0439(15) Uani 1 1 d . . .
H36A H 0.4565 0.7446 0.5241 0.053 Uiso 1 1 calc R . .
C41 C 1.3269(7) 1.2592(6) 0.8293(3) 0.0351(13) Uani 1 1 d . . .
C42 C 1.4754(7) 1.2209(7) 0.8310(4) 0.0425(15) Uani 1 1 d . . .
H42A H 1.4863 1.1268 0.8111 0.051 Uiso 1 1 calc R . .
C43 C 1.6077(6) 1.3198(7) 0.8615(4) 0.0425(15) Uani 1 1 d . . .
H43A H 1.7056 1.2921 0.8615 0.051 Uiso 1 1 calc R . .
C44 C 1.5931(6) 1.4597(7) 0.8918(4) 0.0368(13) Uani 1 1 d . . .
C45 C 1.4460(6) 1.5012(6) 0.8898(4) 0.0369(13) Uani 1 1 d . . .
H45A H 1.4359 1.5956 0.9093 0.044 Uiso 1 1 calc R . .
C46 C 1.3144(6) 1.4021(7) 0.8588(3) 0.0363(13) Uani 1 1 d . . .
H46A H 1.2169 1.4311 0.8577 0.044 Uiso 1 1 calc R . .
C51 C 1.9842(6) 1.7020(7) 0.9504(3) 0.0365(13) Uani 1 1 d . . .
C52 C 2.1062(7) 1.7585(7) 0.9118(4) 0.0433(15) Uani 1 1 d . . .
H52A H 2.1148 1.7154 0.8635 0.052 Uiso 1 1 calc R . .
C53 C 2.2144(7) 1.8772(8) 0.9440(4) 0.0430(15) Uani 1 1 d . . .
H53A H 2.2929 1.9182 0.9172 0.052 Uiso 1 1 calc R . .
C54 C 2.2026(7) 1.9336(7) 1.0177(4) 0.0393(14) Uani 1 1 d . . .
C55 C 2.0863(7) 1.8793(8) 1.0586(3) 0.0417(15) Uani 1 1 d . . .
H55A H 2.0824 1.9190 1.1083 0.050 Uiso 1 1 calc R . .
C56 C 1.9748(7) 1.7638(7) 1.0239(4) 0.0410(14) Uani 1 1 d . . .
H56A H 1.8931 1.7271 1.0499 0.049 Uiso 1 1 calc R . .


_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
Au1 C1 2.012(5) . ?
Au1 P1 2.2802(18) . ?
P1 C11 1.817(5) . ?
P1 C21 1.819(5) . ?
P1 C31 1.821(6) . ?
O1 C3 1.217(7) . ?
O2 N2 1.224(8) . ?
O3 N2 1.215(7) . ?
N1 C3 1.368(7) . ?
N1 C44 1.414(8) . ?
N2 C54 1.477(8) . ?
C1 C2 1.187(8) . ?
C2 C41 1.450(9) . ?
C3 C51 1.498(9) . ?
C11 C12 1.377(8) . ?
C11 C16 1.396(7) . ?
C12 C13 1.401(8) . ?
C13 C14 1.376(9) . ?
C14 C15 1.375(9) . ?
C15 C16 1.395(8) . ?
C21 C26 1.396(8) . ?
C21 C22 1.397(8) . ?
C22 C23 1.392(8) . ?
C23 C24 1.381(11) . ?
C24 C25 1.379(11) . ?
C25 C26 1.382(8) . ?
C31 C32 1.364(8) . ?
C31 C36 1.385(8) . ?
C32 C33 1.380(10) . ?
C33 C34 1.379(11) . ?
C34 C35 1.358(10) . ?
C35 C36 1.401(9) . ?
C41 C42 1.396(7) . ?
C41 C46 1.401(8) . ?
C42 C43 1.391(9) . ?
C43 C44 1.386(8) . ?
C44 C45 1.394(7) . ?
C45 C46 1.389(8) . ?
C51 C52 1.392(8) . ?
C51 C56 1.393(9) . ?
C52 C53 1.375(9) . ?
C53 C54 1.385(9) . ?
C54 C55 1.372(9) . ?
C55 C56 1.385(9) . ?

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 Au1 P1 174.52(14) . . ?
C11 P1 C21 104.4(2) . . ?
C11 P1 C31 105.8(3) . . ?
C21 P1 C31 105.9(3) . . ?
C11 P1 Au1 116.91(19) . . ?
C21 P1 Au1 112.13(19) . . ?
C31 P1 Au1 110.93(19) . . ?
C3 N1 C44 127.6(5) . . ?
O3 N2 O2 124.0(6) . . ?
O3 N2 C54 117.7(6) . . ?
O2 N2 C54 118.3(6) . . ?
C2 C1 Au1 174.3(5) . . ?
C1 C2 C41 177.0(6) . . ?
O1 C3 N1 123.7(6) . . ?
O1 C3 C51 120.6(5) . . ?
N1 C3 C51 115.7(5) . . ?
C12 C11 C16 119.9(5) . . ?
C12 C11 P1 121.7(4) . . ?
C16 C11 P1 118.1(4) . . ?
C11 C12 C13 120.8(5) . . ?
C14 C13 C12 118.8(6) . . ?
C15 C14 C13 121.0(5) . . ?
C14 C15 C16 120.4(5) . . ?
C15 C16 C11 119.0(6) . . ?
C26 C21 C22 119.6(5) . . ?
C26 C21 P1 117.6(4) . . ?
C22 C21 P1 122.9(4) . . ?
C23 C22 C21 118.8(6) . . ?
C24 C23 C22 120.9(7) . . ?
C25 C24 C23 120.4(6) . . ?
C24 C25 C26 119.5(7) . . ?
C25 C26 C21 120.8(6) . . ?
C32 C31 C36 118.5(6) . . ?
C32 C31 P1 119.6(5) . . ?
C36 C31 P1 121.9(4) . . ?
C31 C32 C33 121.0(7) . . ?
C34 C33 C32 121.0(7) . . ?
C35 C34 C33 118.5(7) . . ?
C34 C35 C36 121.0(7) . . ?
C31 C36 C35 120.0(6) . . ?
C42 C41 C46 117.8(5) . . ?
C42 C41 C2 120.6(5) . . ?
C46 C41 C2 121.6(5) . . ?
C43 C42 C41 121.6(5) . . ?
C44 C43 C42 119.7(5) . . ?
C43 C44 C45 119.6(6) . . ?
C43 C44 N1 122.4(5) . . ?
C45 C44 N1 118.0(5) . . ?
C46 C45 C44 120.4(5) . . ?
C45 C46 C41 120.8(5) . . ?
C52 C51 C56 119.3(6) . . ?
C52 C51 C3 116.9(6) . . ?
C56 C51 C3 123.8(6) . . ?
C53 C52 C51 121.0(6) . . ?
C52 C53 C54 117.8(6) . . ?
C55 C54 C53 123.1(6) . . ?
C55 C54 N2 118.5(6) . . ?
C53 C54 N2 118.4(6) . . ?
C54 C55 C56 118.2(6) . . ?
C55 C56 C51 120.5(6) . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
N1 H1A O2 0.86 2.50 3.267(7) 149.7 2_997

_diffrn_measured_fraction_theta_max 0.969
_diffrn_reflns_theta_full        26.00
_diffrn_measured_fraction_theta_full 0.969
_refine_diff_density_max         2.092
_refine_diff_density_min         -1.074
_refine_diff_density_rms         0.142
_database_code_depnum_ccdc_archive 'CCDC 1013703'
