# Supplementary Material (ESI) for Chemical Communications
# This journal is © The Royal Society of Chemistry 2003



data_global
_publ_contact_author_email       nzhu@hkucc.hku.hk
_publ_contact_author_name        'Nianyong Zhu'
_journal_name_full               Chem.Commun.
_journal_coden_Cambridge         0182
_journal_year                    ?
_journal_volume                  ?
_journal_page_first              ?
loop_
_publ_author_name
C.M.Che
R.W.Y.Sun
W.Y.Yu
C.B.Ko
N.Y.Zhu
H.Z.Sun

data_mar629a
_database_code_CSD               201191

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C44 H28 Au Cl N4 O4'
_chemical_formula_sum            'C44 H28 Au Cl N4 O4'
_chemical_formula_weight         909.12

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
Au Au -2.0133 8.8022 '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'
C C 0.0033 0.0016 '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'
O O 0.0106 0.0060 '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'

_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_H-M   'P n n a'

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

_cell_length_a                   8.1020(16)
_cell_length_b                   20.964(4)
_cell_length_c                   20.060(4)
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_volume                     3407.2(12)
_cell_formula_units_Z            4
_cell_measurement_temperature    253(2)
_cell_measurement_reflns_used    0
_cell_measurement_theta_min      0
_cell_measurement_theta_max      0

_exptl_crystal_description       prism
_exptl_crystal_colour            black
_exptl_crystal_size_max          0.4
_exptl_crystal_size_mid          0.1
_exptl_crystal_size_min          0.1
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.772
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1792
_exptl_absorpt_coefficient_mu    4.451
_exptl_absorpt_correction_type   none
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   ?

_exptl_special_details           
;
?
;

_diffrn_ambient_temperature      253(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  'Mar IPDS mar300'
_diffrn_measurement_method       Oscillation
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            13426
_diffrn_reflns_av_R_equivalents  0.0478
_diffrn_reflns_av_sigmaI/netI    0.0756
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_k_min       -24
_diffrn_reflns_limit_k_max       25
_diffrn_reflns_limit_l_min       -24
_diffrn_reflns_limit_l_max       24
_diffrn_reflns_theta_min         1.40
_diffrn_reflns_theta_max         25.63
_reflns_number_total             3066
_reflns_number_gt                1782
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       Marcontrol
_computing_cell_refinement       Scalepack
_computing_data_reduction        Denzo
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1997)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_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^ > 2sigma(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^)+(0.0544P)^2^+0.0000P] 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    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         3066
_refine_ls_number_parameters     248
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0645
_refine_ls_R_factor_gt           0.0308
_refine_ls_wR_factor_ref         0.1040
_refine_ls_wR_factor_gt          0.0790
_refine_ls_goodness_of_fit_ref   0.934
_refine_ls_restrained_S_all      0.934
_refine_ls_shift/su_max          0.000
_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 0.7500 0.0000 0.075073(16) 0.02988(14) Uani 1 2 d S . .
N1 N 0.6872(6) -0.0640(3) 0.0033(3) 0.0294(13) Uani 1 1 d . . .
N2 N 0.6981(6) -0.0656(3) 0.1467(3) 0.0335(14) Uani 1 1 d . . .
C1 C 0.7500 0.0000 -0.0970(4) 0.0295(19) Uani 1 2 d S . .
C2 C 0.6798(9) -0.0522(3) -0.0647(3) 0.0292(15) Uani 1 1 d . . .
C3 C 0.5981(7) -0.1046(4) -0.0948(3) 0.0389(18) Uani 1 1 d . . .
H3 H 0.5737 -0.1084 -0.1399 0.047 Uiso 1 1 calc R . .
C4 C 0.5619(8) -0.1475(3) -0.0476(3) 0.0361(17) Uani 1 1 d . . .
H4 H 0.5088 -0.1863 -0.0545 0.043 Uiso 1 1 calc R . .
C5 C 0.6183(7) -0.1238(3) 0.0147(3) 0.0314(16) Uani 1 1 d . . .
C6 C 0.6128(8) -0.1555(3) 0.0751(3) 0.0347(16) Uani 1 1 d . . .
C7 C 0.6582(8) -0.1284(3) 0.1357(3) 0.0354(16) Uani 1 1 d . . .
C8 C 0.6608(9) -0.1605(4) 0.1978(3) 0.0466(19) Uani 1 1 d . . .
H8 H 0.6411 -0.2037 0.2046 0.056 Uiso 1 1 calc R . .
C9 C 0.6969(9) -0.1173(4) 0.2454(4) 0.046(2) Uani 1 1 d . . .
H9 H 0.7045 -0.1257 0.2908 0.055 Uiso 1 1 calc R . .
C10 C 0.7215(7) -0.0574(4) 0.2153(3) 0.0356(17) Uani 1 1 d . . .
C11 C 0.7500 0.0000 0.2470(5) 0.037(2) Uani 1 2 d S . .
C12 C 0.7500 0.0000 -0.1713(4) 0.034(2) Uani 1 2 d S . .
C13 C 0.8098(8) -0.0516(4) -0.2073(4) 0.0388(18) Uani 1 1 d . . .
H13 H 0.8509 -0.0868 -0.1845 0.047 Uiso 1 1 calc R . .
C14 C 0.8099(10) -0.0518(4) -0.2758(4) 0.056(2) Uani 1 1 d . . .
H14 H 0.8503 -0.0870 -0.2989 0.068 Uiso 1 1 calc R . .
C15 C 0.7500 0.0000 -0.3102(5) 0.051(3) Uani 1 2 d S . .
H15 H 0.7500 0.0000 -0.3566 0.062 Uiso 1 2 calc SR . .
C16 C 0.5565(9) -0.2233(3) 0.0761(3) 0.0373(17) Uani 1 1 d . . .
C17 C 0.6453(9) -0.2687(4) 0.0408(4) 0.050(2) Uani 1 1 d . . .
H17 H 0.7379 -0.2567 0.0164 0.060 Uiso 1 1 calc R . .
C18 C 0.5952(10) -0.3322(4) 0.0420(4) 0.056(2) Uani 1 1 d . . .
H18 H 0.6549 -0.3628 0.0187 0.067 Uiso 1 1 calc R . .
C19 C 0.4583(11) -0.3495(4) 0.0774(4) 0.055(2) Uani 1 1 d . . .
H19 H 0.4254 -0.3919 0.0782 0.067 Uiso 1 1 calc R . .
C20 C 0.3694(10) -0.3048(4) 0.1115(4) 0.052(2) Uani 1 1 d . . .
H20 H 0.2760 -0.3169 0.1352 0.062 Uiso 1 1 calc R . .
C21 C 0.4179(9) -0.2417(4) 0.1107(4) 0.0459(19) Uani 1 1 d . . .
H21 H 0.3564 -0.2114 0.1338 0.055 Uiso 1 1 calc R . .
C22 C 0.7500 0.0000 0.3213(5) 0.043(2) Uani 1 2 d S . .
C23 C 0.6353(10) 0.0364(4) 0.3570(4) 0.058(2) Uani 1 1 d . . .
H23 H 0.5587 0.0610 0.3340 0.070 Uiso 1 1 calc R . .
C24 C 0.6342(13) 0.0362(6) 0.4263(4) 0.078(3) Uani 1 1 d . . .
H24 H 0.5569 0.0602 0.4497 0.094 Uiso 1 1 calc R . .
C25 C 0.7500 0.0000 0.4598(6) 0.084(5) Uani 1 2 d S . .
H25 H 0.7500 0.0000 0.5062 0.100 Uiso 1 2 calc SR . .
Cl1 Cl 0.4475(4) 0.2500 0.2500 0.0678(9) Uani 1 2 d S . .
O1 O 0.5458(8) 0.2630(4) 0.1930(3) 0.114(3) Uani 1 1 d . . .
O2 O 0.3481(10) 0.1969(4) 0.2371(4) 0.134(3) Uani 1 1 d . . .

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 0.0351(2) 0.0277(2) 0.0268(2) 0.000 0.000 0.0031(2)
N1 0.035(3) 0.027(4) 0.026(3) -0.004(3) -0.001(2) 0.001(2)
N2 0.043(3) 0.033(4) 0.024(3) 0.008(3) 0.003(2) 0.001(2)
C1 0.033(5) 0.028(5) 0.027(4) 0.000 0.000 0.006(5)
C2 0.039(3) 0.025(4) 0.023(4) 0.001(3) -0.002(3) 0.005(3)
C3 0.036(4) 0.048(5) 0.033(4) -0.007(4) 0.004(3) -0.001(3)
C4 0.046(4) 0.026(4) 0.036(4) 0.001(3) 0.006(3) -0.002(3)
C5 0.039(4) 0.017(4) 0.037(4) -0.004(3) -0.002(3) -0.004(3)
C6 0.041(4) 0.028(4) 0.035(4) 0.000(4) 0.007(3) 0.002(3)
C7 0.050(4) 0.021(4) 0.036(4) 0.006(3) 0.006(3) 0.003(3)
C8 0.053(5) 0.044(5) 0.043(5) 0.008(4) -0.004(4) 0.002(4)
C9 0.055(4) 0.052(6) 0.031(4) 0.000(4) -0.003(3) -0.001(4)
C10 0.038(4) 0.043(5) 0.026(4) 0.008(3) 0.004(3) 0.001(3)
C11 0.035(5) 0.042(6) 0.032(5) 0.000 0.000 -0.009(6)
C12 0.041(5) 0.035(6) 0.025(5) 0.000 0.000 -0.005(6)
C13 0.042(4) 0.032(5) 0.042(5) -0.005(4) 0.004(3) 0.002(3)
C14 0.062(5) 0.065(6) 0.042(5) -0.007(5) -0.002(4) -0.010(4)
C15 0.056(7) 0.075(9) 0.023(5) 0.000 0.000 -0.009(8)
C16 0.049(4) 0.030(4) 0.033(4) 0.000(4) 0.001(3) 0.001(3)
C17 0.063(5) 0.035(5) 0.052(5) 0.004(4) 0.006(4) 0.001(4)
C18 0.085(6) 0.034(5) 0.049(5) -0.007(4) 0.002(5) 0.010(4)
C19 0.094(7) 0.027(5) 0.045(5) 0.006(4) -0.002(5) -0.013(5)
C20 0.071(6) 0.039(6) 0.045(5) 0.012(4) 0.003(4) -0.008(4)
C21 0.064(5) 0.031(5) 0.042(5) 0.005(4) 0.011(4) 0.004(4)
C22 0.057(6) 0.045(7) 0.027(5) 0.000 0.000 -0.017(7)
C23 0.073(6) 0.064(7) 0.039(5) -0.016(5) 0.012(4) -0.025(5)
C24 0.098(8) 0.086(9) 0.050(6) -0.021(6) 0.029(5) -0.042(7)
C25 0.135(15) 0.085(12) 0.031(7) 0.000 0.000 -0.065(12)
Cl1 0.069(2) 0.069(3) 0.064(2) -0.0142(19) 0.000 0.000
O1 0.115(5) 0.135(7) 0.093(5) 0.016(5) 0.041(5) 0.010(5)
O2 0.169(7) 0.129(7) 0.105(6) -0.024(6) 0.000(6) -0.092(6)

_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 N1 2.032(5) . ?
Au1 N1 2.032(5) 2_655 ?
Au1 N2 2.033(5) 2_655 ?
Au1 N2 2.033(5) . ?
N1 C2 1.389(7) . ?
N1 C5 1.391(8) . ?
N2 C7 1.373(8) . ?
N2 C10 1.400(8) . ?
C1 C2 1.393(8) 2_655 ?
C1 C2 1.393(8) . ?
C1 C12 1.491(12) . ?
C2 C3 1.416(9) . ?
C3 C4 1.339(9) . ?
C4 C5 1.422(9) . ?
C5 C6 1.382(9) . ?
C6 C7 1.392(9) . ?
C6 C16 1.493(9) . ?
C7 C8 1.415(9) . ?
C8 C9 1.347(9) . ?
C9 C10 1.409(10) . ?
C10 C11 1.380(8) . ?
C11 C10 1.380(8) 2_655 ?
C11 C22 1.491(13) . ?
C12 C13 1.387(9) 2_655 ?
C12 C13 1.387(9) . ?
C13 C14 1.376(10) . ?
C14 C15 1.375(10) . ?
C15 C14 1.375(10) 2_655 ?
C16 C21 1.376(9) . ?
C16 C17 1.388(9) . ?
C17 C18 1.392(10) . ?
C18 C19 1.366(10) . ?
C19 C20 1.365(10) . ?
C20 C21 1.379(10) . ?
C22 C23 1.398(10) . ?
C22 C23 1.398(10) 2_655 ?
C23 C24 1.391(11) . ?
C24 C25 1.382(13) . ?
C25 C24 1.382(13) 2_655 ?
Cl1 O2 1.397(7) . ?
Cl1 O2 1.397(7) 3 ?
Cl1 O1 1.421(6) . ?
Cl1 O1 1.421(6) 3 ?

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
N1 Au1 N1 89.8(3) . 2_655 ?
N1 Au1 N2 177.31(19) . 2_655 ?
N1 Au1 N2 90.1(2) 2_655 2_655 ?
N1 Au1 N2 90.1(2) . . ?
N1 Au1 N2 177.31(19) 2_655 . ?
N2 Au1 N2 90.1(3) 2_655 . ?
C2 N1 C5 107.7(6) . . ?
C2 N1 Au1 126.2(5) . . ?
C5 N1 Au1 125.4(4) . . ?
C7 N2 C10 107.9(6) . . ?
C7 N2 Au1 125.8(5) . . ?
C10 N2 Au1 125.6(5) . . ?
C2 C1 C2 124.6(8) 2_655 . ?
C2 C1 C12 117.7(4) 2_655 . ?
C2 C1 C12 117.7(4) . . ?
N1 C2 C1 125.4(6) . . ?
N1 C2 C3 107.5(6) . . ?
C1 C2 C3 127.0(6) . . ?
C4 C3 C2 108.8(6) . . ?
C3 C4 C5 108.4(6) . . ?
C6 C5 N1 126.2(6) . . ?
C6 C5 C4 126.2(6) . . ?
N1 C5 C4 107.5(6) . . ?
C5 C6 C7 124.1(7) . . ?
C5 C6 C16 118.7(6) . . ?
C7 C6 C16 117.2(6) . . ?
N2 C7 C6 126.4(6) . . ?
N2 C7 C8 108.1(6) . . ?
C6 C7 C8 125.4(7) . . ?
C9 C8 C7 107.9(7) . . ?
C8 C9 C10 109.0(7) . . ?
C11 C10 N2 125.8(7) . . ?
C11 C10 C9 127.1(7) . . ?
N2 C10 C9 107.0(6) . . ?
C10 C11 C10 125.0(9) . 2_655 ?
C10 C11 C22 117.5(4) . . ?
C10 C11 C22 117.5(4) 2_655 . ?
C13 C12 C13 117.4(9) 2_655 . ?
C13 C12 C1 121.3(4) 2_655 . ?
C13 C12 C1 121.3(4) . . ?
C14 C13 C12 121.5(8) . . ?
C15 C14 C13 119.9(8) . . ?
C14 C15 C14 119.8(10) 2_655 . ?
C21 C16 C17 119.3(7) . . ?
C21 C16 C6 121.6(7) . . ?
C17 C16 C6 119.2(6) . . ?
C16 C17 C18 119.7(7) . . ?
C19 C18 C17 119.9(8) . . ?
C20 C19 C18 120.5(8) . . ?
C19 C20 C21 120.2(8) . . ?
C16 C21 C20 120.4(7) . . ?
C23 C22 C23 118.5(10) . 2_655 ?
C23 C22 C11 120.7(5) . . ?
C23 C22 C11 120.7(5) 2_655 . ?
C24 C23 C22 121.0(10) . . ?
C25 C24 C23 118.9(11) . . ?
C24 C25 C24 121.7(12) . 2_655 ?
O2 Cl1 O2 109.6(8) . 3 ?
O2 Cl1 O1 109.1(5) . . ?
O2 Cl1 O1 108.6(5) 3 . ?
O2 Cl1 O1 108.6(5) . 3 ?
O2 Cl1 O1 109.1(5) 3 3 ?
O1 Cl1 O1 111.8(6) . 3 ?

_diffrn_measured_fraction_theta_max 0.953
_diffrn_reflns_theta_full        25.63
_diffrn_measured_fraction_theta_full 0.953
_refine_diff_density_max         0.716
_refine_diff_density_min         -1.590
_refine_diff_density_rms         0.265