# Electronic Supplementary Material (ESI) for RSC Advances
# This journal is © The Royal Society of Chemistry 2014

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#                                CCDC 
# 
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# 
#  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.
#
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#  fide research purposes only. It may contain copyright material
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data_jmi_11_5_0ma

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
 ?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C18 H15 Au Cl P'
_chemical_formula_sum            'C18 H15 Au Cl P'
_chemical_formula_weight         494.69

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'
P P 0.1023 0.0942 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cl Cl 0.1484 0.1585 '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   'P n m a'
_symmetry_space_group_name_Hall  '-P 2ac 2n'
_symmetry_Int_Tables_number      62


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

_cell_length_a                   24.7714(11)
_cell_length_b                   17.0229(7)
_cell_length_c                   7.5234(3)
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_volume                     3172.5(2)
_cell_formula_units_Z            8
_cell_measurement_temperature    200(2)
_cell_measurement_reflns_used    9921
_cell_measurement_theta_min      2.5
_cell_measurement_theta_max      30.1

_exptl_crystal_description       prism
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.22
_exptl_crystal_size_mid          0.11
_exptl_crystal_size_min          0.11
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    2.071
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1872
_exptl_absorpt_coefficient_mu    9.533
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.545
_exptl_absorpt_correction_T_max  0.746
_exptl_absorpt_process_details   
;
SADABS, Bruker AXS Inc., Madison, 
Wisconsin, USA.
;

_diffrn_ambient_temperature      200(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 APEX-II CCD'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         0
_diffrn_standards_interval_count ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            19125
_diffrn_reflns_av_R_equivalents  0.0165
_diffrn_reflns_av_sigmaI/netI    0.0141
_diffrn_reflns_limit_h_min       -28
_diffrn_reflns_limit_h_max       34
_diffrn_reflns_limit_k_min       -21
_diffrn_reflns_limit_k_max       23
_diffrn_reflns_limit_l_min       -10
_diffrn_reflns_limit_l_max       5
_diffrn_reflns_theta_min         2.90
_diffrn_reflns_theta_max         29.57
_reflns_number_total             4586
_reflns_number_gt                4058
_reflns_threshold_expression     >2\s(I)

_computing_data_collection       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SIR92 (Giacovazzo et al, 1993)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_molecular_graphics    'Ortep-3 for Windows (Farrugia, 1997)'
_computing_publication_material  'WinGX publication routines (Farrugia, 1999)'

_refine_special_details          
;
 Refinement of F^2^ against ALL reflections.  The weighted R-factor wR and
 goodness of fit S are based on F^2^, conventional R-factors R are based
 on F, with F set to zero for negative F^2^. The threshold expression of
 F^2^ > 2\s(F^2^) is used only for calculating R-factors(gt) etc. and is
 not relevant to the choice of reflections for refinement.  R-factors based
 on F^2^ 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/[\s^2^(Fo^2^)+(0.0117P)^2^+4.4642P] where P=(Fo^2^+2Fc^2^)/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     SHELXL
_refine_ls_extinction_coef       0.00136(3)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^
_refine_ls_number_reflns         4586
_refine_ls_number_parameters     208
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0191
_refine_ls_R_factor_gt           0.0141
_refine_ls_wR_factor_ref         0.0317
_refine_ls_wR_factor_gt          0.0297
_refine_ls_goodness_of_fit_ref   0.906
_refine_ls_restrained_S_all      0.906
_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 0.397633(4) 0.2500 0.343114(14) 0.02134(3) Uani 1 2 d S . .
Cl1 Cl 0.48837(3) 0.2500 0.38190(10) 0.03219(15) Uani 1 2 d S . .
P1 P 0.30897(3) 0.2500 0.31307(9) 0.02031(13) Uani 1 2 d S . .
C1 C 0.26776(7) 0.16871(11) 0.2995(2) 0.0203(3) Uani 1 1 d . . .
C2 C 0.21267(7) 0.17855(12) 0.2678(3) 0.0240(4) Uani 1 1 d . . .
H2 H 0.1914 0.1322 0.2601 0.029 Uiso 1 1 calc R . .
C3 C 0.18595(10) 0.2500 0.2463(4) 0.0243(5) Uani 1 2 d S . .
C4 C 0.12706(11) 0.2500 0.1973(4) 0.0315(6) Uani 1 2 d S . .
H4A H 0.1130 0.1963 0.2038 0.047 Uiso 0.50 1 calc PR . .
H4B H 0.1228 0.2701 0.0760 0.047 Uiso 0.50 1 calc PR . .
H4C H 0.1071 0.2836 0.2801 0.047 Uiso 0.50 1 calc PR . .
C6 C 0.27208(8) 0.02732(12) 0.2093(3) 0.0257(4) Uani 1 1 d . . .
H6 H 0.2435 0.0367 0.1280 0.031 Uiso 1 1 calc R . .
C7 C 0.29433(9) -0.04707(12) 0.2229(3) 0.0288(4) Uani 1 1 d . . .
H7 H 0.2808 -0.0883 0.1504 0.035 Uiso 1 1 calc R . .
C8 C 0.33612(8) -0.06205(12) 0.3412(3) 0.0279(4) Uani 1 1 d . . .
H8 H 0.3511 -0.1133 0.3501 0.033 Uiso 1 1 calc R . .
C9 C 0.35564(8) -0.00171(12) 0.4460(3) 0.0258(4) Uani 1 1 d . . .
H9 H 0.3843 -0.0115 0.5269 0.031 Uiso 1 1 calc R . .
C10 C 0.33370(7) 0.07305(11) 0.4338(2) 0.0227(4) Uani 1 1 d . . .
H10 H 0.3474 0.1140 0.5068 0.027 Uiso 1 1 calc R . .
Au2 Au 0.528819(4) 0.2500 0.851213(14) 0.02111(3) Uani 1 2 d S . .
Cl2 Cl 0.62056(3) 0.2500 0.83760(10) 0.02942(14) Uani 1 2 d S . .
P2 P 0.43984(3) 0.2500 0.85825(10) 0.01992(13) Uani 1 2 d S . .
C5 C 0.29158(7) 0.08872(11) 0.3149(2) 0.0205(3) Uani 1 1 d . . .
C11 C 0.39859(7) 0.16879(10) 0.8469(2) 0.0186(3) Uani 1 1 d . . .
C12 C 0.34261(7) 0.17840(11) 0.8442(2) 0.0203(3) Uani 1 1 d . . .
H12 H 0.3212 0.1321 0.8442 0.024 Uiso 1 1 calc R . .
C13 C 0.31538(10) 0.2500 0.8415(3) 0.0193(5) Uani 1 2 d S . .
C14 C 0.25502(11) 0.2500 0.8267(4) 0.0250(5) Uani 1 2 d S . .
H14A H 0.2411 0.3020 0.8585 0.038 Uiso 0.50 1 calc PR . .
H14B H 0.2400 0.2105 0.9076 0.038 Uiso 0.50 1 calc PR . .
H14C H 0.2446 0.2374 0.7043 0.038 Uiso 0.50 1 calc PR . .
C15 C 0.42242(7) 0.08885(10) 0.8430(2) 0.0199(3) Uani 1 1 d . . .
C16 C 0.39918(8) 0.02907(12) 0.9443(3) 0.0268(4) Uani 1 1 d . . .
H16 H 0.3690 0.0403 1.0179 0.032 Uiso 1 1 calc R . .
C17 C 0.41978(9) -0.04647(12) 0.9382(3) 0.0314(4) Uani 1 1 d . . .
H17 H 0.4033 -0.0870 1.0060 0.038 Uiso 1 1 calc R . .
C18 C 0.46431(9) -0.06319(12) 0.8338(3) 0.0302(4) Uani 1 1 d . . .
H18 H 0.4785 -0.1150 0.8304 0.036 Uiso 1 1 calc R . .
C19 C 0.48801(8) -0.00428(12) 0.7343(3) 0.0284(4) Uani 1 1 d . . .
H19 H 0.5188 -0.0157 0.6635 0.034 Uiso 1 1 calc R . .
C20 C 0.46717(7) 0.07149(11) 0.7372(3) 0.0240(4) Uani 1 1 d . . .
H20 H 0.4834 0.1115 0.6671 0.029 Uiso 1 1 calc R . .

loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_23
_atom_site_aniso_U_13
_atom_site_aniso_U_12
Au1 0.01655(5) 0.02090(5) 0.02656(5) 0.000 0.00065(4) 0.000
Cl1 0.0171(3) 0.0389(4) 0.0406(4) 0.000 0.0008(3) 0.000
P1 0.0159(3) 0.0181(3) 0.0269(3) 0.000 -0.0004(2) 0.000
C1 0.0193(8) 0.0203(9) 0.0214(8) -0.0011(7) 0.0014(6) -0.0017(7)
C2 0.0200(8) 0.0265(9) 0.0256(9) -0.0004(8) 0.0005(7) -0.0035(7)
C3 0.0180(12) 0.0311(14) 0.0237(13) 0.000 -0.0002(10) 0.000
C4 0.0189(13) 0.0382(17) 0.0373(16) 0.000 -0.0037(11) 0.000
C6 0.0257(9) 0.0257(10) 0.0258(9) -0.0014(8) -0.0020(8) -0.0059(8)
C7 0.0346(10) 0.0222(9) 0.0296(10) -0.0052(8) 0.0010(8) -0.0069(8)
C8 0.0311(10) 0.0200(9) 0.0326(10) -0.0002(8) 0.0062(8) 0.0006(8)
C9 0.0231(9) 0.0264(10) 0.0279(9) 0.0015(8) -0.0001(7) 0.0001(8)
C10 0.0231(9) 0.0223(9) 0.0228(9) -0.0025(7) -0.0018(7) -0.0022(7)
Au2 0.01739(5) 0.01793(5) 0.02801(5) 0.000 0.00045(4) 0.000
Cl2 0.0183(3) 0.0258(3) 0.0442(4) 0.000 0.0032(3) 0.000
P2 0.0169(3) 0.0156(3) 0.0273(3) 0.000 -0.0009(2) 0.000
C5 0.0196(8) 0.0205(9) 0.0215(8) 0.0004(7) 0.0025(7) -0.0022(7)
C11 0.0199(8) 0.0163(8) 0.0198(8) -0.0001(6) 0.0011(6) -0.0001(6)
C12 0.0203(8) 0.0185(8) 0.0221(8) -0.0003(7) 0.0005(7) -0.0020(7)
C13 0.0175(11) 0.0212(12) 0.0192(11) 0.000 0.0019(9) 0.000
C14 0.0201(12) 0.0230(13) 0.0320(14) 0.000 0.0010(11) 0.000
C15 0.0200(8) 0.0174(8) 0.0225(8) 0.0000(7) -0.0015(7) 0.0009(6)
C16 0.0267(10) 0.0227(9) 0.0310(10) 0.0019(8) 0.0040(8) 0.0011(7)
C17 0.0382(11) 0.0200(9) 0.0360(11) 0.0047(8) 0.0013(9) 0.0015(8)
C18 0.0358(11) 0.0207(9) 0.0341(11) -0.0039(8) -0.0054(9) 0.0093(8)
C19 0.0264(10) 0.0294(10) 0.0296(10) -0.0071(8) -0.0004(8) 0.0068(8)
C20 0.0229(9) 0.0235(9) 0.0257(9) -0.0018(8) 0.0015(7) -0.0001(7)

_geom_special_details            
;
 All s.u.'s (except the s.u. in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell s.u.'s are taken
 into account individually in the estimation of s.u.'s in distances, angles
 and torsion angles; correlations between s.u.'s in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell s.u.'s is used for estimating s.u.'s 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 P1 2.2078(7) . ?
Au1 Cl1 2.2666(7) . ?
P1 C1 1.7227(18) . ?
P1 C1 1.7227(18) 8_565 ?
C1 C2 1.395(2) . ?
C1 C5 1.488(3) . ?
C2 C3 1.394(2) . ?
C2 H2 0.9500 . ?
C3 C2 1.394(2) 8_565 ?
C3 C4 1.505(4) . ?
C4 H4A 0.9800 . ?
C4 H4B 0.9800 . ?
C4 H4C 0.9800 . ?
C6 C7 1.385(3) . ?
C6 C5 1.399(3) . ?
C6 H6 0.9500 . ?
C7 C8 1.389(3) . ?
C7 H7 0.9500 . ?
C8 C9 1.382(3) . ?
C8 H8 0.9500 . ?
C9 C10 1.387(3) . ?
C9 H9 0.9500 . ?
C10 C5 1.400(3) . ?
C10 H10 0.9500 . ?
Au2 P2 2.2047(7) . ?
Au2 Cl2 2.2749(7) . ?
P2 C11 1.7213(18) . ?
P2 C11 1.7213(18) 8_565 ?
C11 C12 1.396(2) . ?
C11 C15 1.484(2) . ?
C12 C13 1.393(2) . ?
C12 H12 0.9500 . ?
C13 C12 1.393(2) 8_565 ?
C13 C14 1.499(4) . ?
C14 H14A 0.9800 . ?
C14 H14B 0.9800 . ?
C14 H14C 0.9800 . ?
C15 C16 1.396(3) . ?
C15 C20 1.397(3) . ?
C16 C17 1.384(3) . ?
C16 H16 0.9500 . ?
C17 C18 1.384(3) . ?
C17 H17 0.9500 . ?
C18 C19 1.382(3) . ?
C18 H18 0.9500 . ?
C19 C20 1.389(3) . ?
C19 H19 0.9500 . ?
C20 H20 0.9500 . ?

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
P1 Au1 Cl1 178.48(3) . . ?
C1 P1 C1 106.90(13) . 8_565 ?
C1 P1 Au1 126.55(6) . . ?
C1 P1 Au1 126.55(6) 8_565 . ?
C2 C1 C5 120.72(16) . . ?
C2 C1 P1 119.55(15) . . ?
C5 C1 P1 119.69(13) . . ?
C1 C2 C3 126.09(19) . . ?
C1 C2 H2 117.0 . . ?
C3 C2 H2 117.0 . . ?
C2 C3 C2 121.5(2) 8_565 . ?
C2 C3 C4 119.26(12) 8_565 . ?
C2 C3 C4 119.26(12) . . ?
C3 C4 H4A 109.5 . . ?
C3 C4 H4B 109.5 . . ?
H4A C4 H4B 109.5 . . ?
C3 C4 H4C 109.5 . . ?
H4A C4 H4C 109.5 . . ?
H4B C4 H4C 109.5 . . ?
C7 C6 C5 120.26(18) . . ?
C7 C6 H6 119.9 . . ?
C5 C6 H6 119.9 . . ?
C6 C7 C8 120.78(18) . . ?
C6 C7 H7 119.6 . . ?
C8 C7 H7 119.6 . . ?
C9 C8 C7 119.32(19) . . ?
C9 C8 H8 120.3 . . ?
C7 C8 H8 120.3 . . ?
C8 C9 C10 120.48(18) . . ?
C8 C9 H9 119.8 . . ?
C10 C9 H9 119.8 . . ?
C9 C10 C5 120.61(17) . . ?
C9 C10 H10 119.7 . . ?
C5 C10 H10 119.7 . . ?
P2 Au2 Cl2 178.80(3) . . ?
C11 P2 C11 106.87(12) . 8_565 ?
C11 P2 Au2 126.32(6) . . ?
C11 P2 Au2 126.32(6) 8_565 . ?
C6 C5 C10 118.54(18) . . ?
C6 C5 C1 120.15(17) . . ?
C10 C5 C1 121.30(16) . . ?
C12 C11 C15 120.15(16) . . ?
C12 C11 P2 119.75(14) . . ?
C15 C11 P2 120.10(13) . . ?
C13 C12 C11 125.70(18) . . ?
C13 C12 H12 117.2 . . ?
C11 C12 H12 117.2 . . ?
C12 C13 C12 122.1(2) 8_565 . ?
C12 C13 C14 118.94(12) 8_565 . ?
C12 C13 C14 118.94(12) . . ?
C13 C14 H14A 109.5 . . ?
C13 C14 H14B 109.5 . . ?
H14A C14 H14B 109.5 . . ?
C13 C14 H14C 109.5 . . ?
H14A C14 H14C 109.5 . . ?
H14B C14 H14C 109.5 . . ?
C16 C15 C20 118.98(17) . . ?
C16 C15 C11 119.60(16) . . ?
C20 C15 C11 121.42(16) . . ?
C17 C16 C15 120.49(19) . . ?
C17 C16 H16 119.8 . . ?
C15 C16 H16 119.8 . . ?
C18 C17 C16 120.2(2) . . ?
C18 C17 H17 119.9 . . ?
C16 C17 H17 119.9 . . ?
C19 C18 C17 119.78(19) . . ?
C19 C18 H18 120.1 . . ?
C17 C18 H18 120.1 . . ?
C18 C19 C20 120.50(19) . . ?
C18 C19 H19 119.7 . . ?
C20 C19 H19 119.7 . . ?
C19 C20 C15 120.00(18) . . ?
C19 C20 H20 120.0 . . ?
C15 C20 H20 120.0 . . ?

_diffrn_measured_fraction_theta_max 0.999
_diffrn_reflns_theta_full        29.57
_diffrn_measured_fraction_theta_full 0.999
_refine_diff_density_max         0.529
_refine_diff_density_min         -0.993
_refine_diff_density_rms         0.079
_database_code_depnum_ccdc_archive 'CCDC 945516'