#------------------------------------------------------------------------------
#$Date: 2016-02-16 22:30:59 +0200 (Tue, 16 Feb 2016) $
#$Revision: 176467 $
#$URL: svn://www.crystallography.net/cod/cif/4/02/84/4028460.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_4028460
loop_
_publ_author_name
'Wan Teng Teo'
'Weidong Rao'
'Ming Joo Koh'
'Philip Wai Hong Chan'
_publ_section_title
;
 Gold-Catalyzed Domino Aminocyclization/1,3-Sulfonyl Migration of
 N-Substituted N-Sulfonyl-aminobut-3-yn-2-ols to 1-Substituted
 3-Sulfonyl-1H-pyrroles
;
_journal_name_full               'Journal of Organic Chemistry'
_journal_page_first              7508
_journal_page_last               7517
_journal_paper_doi               10.1021/jo401083m
_journal_volume                  78
_journal_year                    2013
_chemical_formula_sum            'C28 H38.5 Au F2 N2 O2.25 P'
_chemical_formula_weight         705.04
_chemical_name_systematic
; 
 ? 
;
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2yn'
_symmetry_space_group_name_H-M   'P 1 21/n 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                 104.180(2)
_cell_angle_gamma                90.00
_cell_formula_units_Z            8
_cell_length_a                   18.7732(6)
_cell_length_b                   15.9334(5)
_cell_length_c                   20.2459(7)
_cell_measurement_reflns_used    9910
_cell_measurement_temperature    103(2)
_cell_measurement_theta_max      31.01
_cell_measurement_theta_min      2.44
_cell_volume                     5871.5(3)
_computing_cell_refinement       'Bruker SAINT'
_computing_data_collection       'Bruker APEX2'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      103(2)
_diffrn_measured_fraction_theta_full 0.995
_diffrn_measured_fraction_theta_max 0.995
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_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  0.0680
_diffrn_reflns_av_sigmaI/netI    0.0788
_diffrn_reflns_limit_h_max       26
_diffrn_reflns_limit_h_min       -27
_diffrn_reflns_limit_k_max       23
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       29
_diffrn_reflns_limit_l_min       -29
_diffrn_reflns_number            67782
_diffrn_reflns_theta_full        31.06
_diffrn_reflns_theta_max         31.06
_diffrn_reflns_theta_min         2.08
_exptl_absorpt_coefficient_mu    5.106
_exptl_absorpt_correction_T_max  0.4283
_exptl_absorpt_correction_T_min  0.2346
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   sadabs
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.595
_exptl_crystal_description       plate
_exptl_crystal_F_000             2804
_exptl_crystal_size_max          0.40
_exptl_crystal_size_mid          0.40
_exptl_crystal_size_min          0.20
_refine_diff_density_max         4.488
_refine_diff_density_min         -3.890
_refine_diff_density_rms         0.268
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.065
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     691
_refine_ls_number_reflns         18750
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.065
_refine_ls_R_factor_all          0.0932
_refine_ls_R_factor_gt           0.0434
_refine_ls_shift/su_max          0.002
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0563P)²+0.8716P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0933
_refine_ls_wR_factor_ref         0.1193
_reflns_number_gt                12895
_reflns_number_total             18750
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            jo401083m_si_002.cif
_cod_data_source_block           chan166s
_cod_original_formula_sum        'C28 H38.50 Au F2 N2 O2.25 P'
_cod_database_code               4028460
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, -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 0.236363(10) 0.136217(12) 0.722376(10) 0.01700(5) Uani 1 1 d . . .
Au2 Au 0.204894(11) 0.160760(12) 0.206873(10) 0.01895(6) Uani 1 1 d . . .
C1 C 0.2559(2) 0.2120(3) 0.6534(2) 0.0109(9) Uani 1 1 d . . .
C2 C 0.2687(3) 0.2746(3) 0.5576(3) 0.0175(10) Uani 1 1 d . . .
H2 H 0.2695 0.2827 0.5113 0.021 Uiso 1 1 calc R . .
C3 C 0.2833(3) 0.3322(3) 0.6063(3) 0.0181(10) Uani 1 1 d . . .
H3 H 0.2968 0.3889 0.6016 0.022 Uiso 1 1 calc R . .
C4 C 0.2313(3) 0.1237(3) 0.5488(3) 0.0150(9) Uani 1 1 d . . .
C5 C 0.2858(3) 0.0771(3) 0.5288(3) 0.0180(10) Uani 1 1 d . . .
C6 C 0.3662(3) 0.1027(3) 0.5511(3) 0.0212(11) Uani 1 1 d . . .
H6 H 0.3681 0.1655 0.5503 0.025 Uiso 1 1 calc R . .
C7 C 0.4008(3) 0.0747(4) 0.6238(3) 0.0294(13) Uani 1 1 d . . .
H7A H 0.3711 0.0952 0.6540 0.044 Uiso 1 1 calc R . .
H7B H 0.4506 0.0975 0.6384 0.044 Uiso 1 1 calc R . .
H7C H 0.4028 0.0132 0.6256 0.044 Uiso 1 1 calc R . .
C8 C 0.4129(3) 0.0701(4) 0.5036(4) 0.0387(16) Uani 1 1 d . . .
H8A H 0.4146 0.0087 0.5054 0.058 Uiso 1 1 calc R . .
H8B H 0.4628 0.0926 0.5184 0.058 Uiso 1 1 calc R . .
H8C H 0.3908 0.0883 0.4568 0.058 Uiso 1 1 calc R . .
C9 C 0.2638(3) 0.0066(3) 0.4890(3) 0.0229(11) Uani 1 1 d . . .
H9 H 0.2996 -0.0268 0.4753 0.027 Uiso 1 1 calc R . .
C10 C 0.1903(3) -0.0161(3) 0.4690(3) 0.0260(12) Uani 1 1 d . . .
H10 H 0.1762 -0.0642 0.4411 0.031 Uiso 1 1 calc R . .
C11 C 0.1377(3) 0.0306(3) 0.4893(3) 0.0228(11) Uani 1 1 d . . .
H11 H 0.0877 0.0138 0.4757 0.027 Uiso 1 1 calc R . .
C12 C 0.1567(3) 0.1025(3) 0.5297(3) 0.0183(10) Uani 1 1 d . . .
C13 C 0.0969(3) 0.1541(3) 0.5479(3) 0.0237(11) Uani 1 1 d . . .
H13 H 0.1206 0.2032 0.5755 0.028 Uiso 1 1 calc R . .
C14 C 0.0570(3) 0.1032(4) 0.5913(4) 0.0408(16) Uani 1 1 d . . .
H14A H 0.0334 0.0546 0.5653 0.061 Uiso 1 1 calc R . .
H14B H 0.0196 0.1384 0.6040 0.061 Uiso 1 1 calc R . .
H14C H 0.0923 0.0840 0.6326 0.061 Uiso 1 1 calc R . .
C15 C 0.0438(3) 0.1876(5) 0.4839(3) 0.0432(17) Uani 1 1 d . . .
H15A H 0.0712 0.2190 0.4566 0.065 Uiso 1 1 calc R . .
H15B H 0.0079 0.2248 0.4968 0.065 Uiso 1 1 calc R . .
H15C H 0.0181 0.1405 0.4571 0.065 Uiso 1 1 calc R . .
C16 C 0.2809(3) 0.3354(3) 0.7294(3) 0.0156(10) Uani 1 1 d . . .
C17 C 0.3481(3) 0.3352(3) 0.7773(3) 0.0166(10) Uani 1 1 d . . .
C18 C 0.4150(3) 0.2882(3) 0.7662(3) 0.0212(11) Uani 1 1 d . . .
H18 H 0.4027 0.2660 0.7185 0.025 Uiso 1 1 calc R . .
C19 C 0.4813(3) 0.3466(4) 0.7746(3) 0.0351(15) Uani 1 1 d . . .
H19A H 0.4678 0.3953 0.7446 0.053 Uiso 1 1 calc R . .
H19B H 0.5218 0.3164 0.7626 0.053 Uiso 1 1 calc R . .
H19C H 0.4967 0.3655 0.8220 0.053 Uiso 1 1 calc R . .
C20 C 0.4326(3) 0.2141(3) 0.8148(3) 0.0286(13) Uani 1 1 d . . .
H20A H 0.4433 0.2345 0.8619 0.043 Uiso 1 1 calc R . .
H20B H 0.4754 0.1840 0.8072 0.043 Uiso 1 1 calc R . .
H20C H 0.3903 0.1760 0.8067 0.043 Uiso 1 1 calc R . .
C21 C 0.3515(3) 0.3781(3) 0.8379(3) 0.0209(11) Uani 1 1 d . . .
H21 H 0.3966 0.3797 0.8718 0.025 Uiso 1 1 calc R . .
C22 C 0.2909(3) 0.4180(3) 0.8496(3) 0.0242(12) Uani 1 1 d . . .
H22 H 0.2948 0.4476 0.8911 0.029 Uiso 1 1 calc R . .
C23 C 0.2245(3) 0.4157(3) 0.8017(3) 0.0243(12) Uani 1 1 d . . .
H23 H 0.1826 0.4417 0.8112 0.029 Uiso 1 1 calc R . .
C24 C 0.2183(3) 0.3754(3) 0.7390(3) 0.0198(11) Uani 1 1 d . . .
C25 C 0.1452(3) 0.3752(4) 0.6864(3) 0.0295(13) Uani 1 1 d . . .
H25 H 0.1536 0.3516 0.6432 0.035 Uiso 1 1 calc R . .
C26 C 0.0899(3) 0.3184(5) 0.7091(4) 0.0457(18) Uani 1 1 d . . .
H26A H 0.1084 0.2606 0.7138 0.069 Uiso 1 1 calc R . .
H26B H 0.0427 0.3201 0.6750 0.069 Uiso 1 1 calc R . .
H26C H 0.0830 0.3379 0.7530 0.069 Uiso 1 1 calc R . .
C27 C 0.1153(3) 0.4647(4) 0.6714(4) 0.0428(17) Uani 1 1 d . . .
H27A H 0.1043 0.4885 0.7125 0.064 Uiso 1 1 calc R . .
H27B H 0.0704 0.4633 0.6346 0.064 Uiso 1 1 calc R . .
H27C H 0.1522 0.4996 0.6576 0.064 Uiso 1 1 calc R . .
C28 C 0.2107(3) 0.0785(3) 0.1370(3) 0.0168(10) Uani 1 1 d . . .
C29 C 0.2236(3) -0.0451(3) 0.0877(3) 0.0228(11) Uani 1 1 d . . .
H29 H 0.2338 -0.1027 0.0824 0.027 Uiso 1 1 calc R . .
C30 C 0.2018(3) 0.0110(3) 0.0377(3) 0.0221(11) Uani 1 1 d . . .
H30 H 0.1930 0.0010 -0.0099 0.026 Uiso 1 1 calc R . .
C31 C 0.2475(3) -0.0420(3) 0.2158(3) 0.0204(11) Uani 1 1 d . . .
C32 C 0.1932(3) -0.0887(3) 0.2361(3) 0.0256(12) Uani 1 1 d . . .
C33 C 0.1157(3) -0.0933(3) 0.1928(3) 0.0300(13) Uani 1 1 d . . .
H33 H 0.1179 -0.0852 0.1443 0.036 Uiso 1 1 calc R . .
C34 C 0.0701(3) -0.0210(4) 0.2110(4) 0.0427(17) Uani 1 1 d . . .
H34A H 0.0659 -0.0278 0.2580 0.064 Uiso 1 1 calc R . .
H34B H 0.0210 -0.0215 0.1801 0.064 Uiso 1 1 calc R . .
H34C H 0.0943 0.0325 0.2067 0.064 Uiso 1 1 calc R . .
C35 C 0.0788(4) -0.1778(4) 0.1972(4) 0.0474(19) Uani 1 1 d . . .
H35A H 0.1102 -0.2230 0.1877 0.071 Uiso 1 1 calc R . .
H35B H 0.0313 -0.1796 0.1638 0.071 Uiso 1 1 calc R . .
H35C H 0.0712 -0.1851 0.2431 0.071 Uiso 1 1 calc R . .
C36 C 0.2146(4) -0.1266(3) 0.2994(3) 0.0341(15) Uani 1 1 d . . .
H36 H 0.1795 -0.1586 0.3153 0.041 Uiso 1 1 calc R . .
C37 C 0.2846(4) -0.1199(4) 0.3402(3) 0.0371(16) Uani 1 1 d . . .
H37 H 0.2971 -0.1471 0.3832 0.045 Uiso 1 1 calc R . .
C38 C 0.3364(4) -0.0738(4) 0.3184(3) 0.0352(15) Uani 1 1 d . . .
H38 H 0.3846 -0.0689 0.3470 0.042 Uiso 1 1 calc R . .
C39 C 0.3194(3) -0.0339(3) 0.2550(3) 0.0262(12) Uani 1 1 d . . .
C40 C 0.3779(3) 0.0131(4) 0.2308(4) 0.0402(16) Uani 1 1 d . . .
H40 H 0.3535 0.0447 0.1887 0.048 Uiso 1 1 calc R . .
C41 C 0.4309(3) -0.0499(6) 0.2119(4) 0.058(2) Uani 1 1 d . . .
H41A H 0.4567 -0.0806 0.2528 0.087 Uiso 1 1 calc R . .
H41B H 0.4668 -0.0199 0.1927 0.087 Uiso 1 1 calc R . .
H41C H 0.4034 -0.0895 0.1782 0.087 Uiso 1 1 calc R . .
C42 C 0.4179(4) 0.0754(5) 0.2825(5) 0.061(2) Uani 1 1 d . . .
H42A H 0.3823 0.1127 0.2959 0.091 Uiso 1 1 calc R . .
H42B H 0.4513 0.1088 0.2627 0.091 Uiso 1 1 calc R . .
H42C H 0.4462 0.0455 0.3228 0.091 Uiso 1 1 calc R . .
C43 C 0.1728(3) 0.1646(3) 0.0326(3) 0.0185(10) Uani 1 1 d . . .
C44 C 0.1007(3) 0.1913(3) 0.0234(3) 0.0222(11) Uani 1 1 d . . .
C45 C 0.0427(3) 0.1452(4) 0.0500(3) 0.0308(13) Uani 1 1 d . . .
H45 H 0.0667 0.0947 0.0753 0.037 Uiso 1 1 calc R . .
C46 C -0.0190(4) 0.1145(5) -0.0083(4) 0.052(2) Uani 1 1 d . . .
H46A H -0.0452 0.1628 -0.0327 0.079 Uiso 1 1 calc R . .
H46B H -0.0531 0.0801 0.0098 0.079 Uiso 1 1 calc R . .
H46C H 0.0016 0.0808 -0.0396 0.079 Uiso 1 1 calc R . .
C47 C 0.0118(4) 0.1977(5) 0.0995(4) 0.0467(18) Uani 1 1 d . . .
H47A H -0.0109 0.2487 0.0765 0.070 Uiso 1 1 calc R . .
H47B H 0.0517 0.2132 0.1387 0.070 Uiso 1 1 calc R . .
H47C H -0.0252 0.1650 0.1151 0.070 Uiso 1 1 calc R . .
C48 C 0.0812(3) 0.2653(3) -0.0139(3) 0.0313(13) Uani 1 1 d . . .
H48 H 0.0324 0.2858 -0.0215 0.038 Uiso 1 1 calc R . .
C49 C 0.1318(4) 0.3091(4) -0.0399(3) 0.0389(16) Uani 1 1 d . . .
H49 H 0.1176 0.3594 -0.0648 0.047 Uiso 1 1 calc R . .
C50 C 0.2026(4) 0.2800(4) -0.0297(3) 0.0356(15) Uani 1 1 d . . .
H50 H 0.2369 0.3107 -0.0478 0.043 Uiso 1 1 calc R . .
C51 C 0.2248(3) 0.2068(3) 0.0063(3) 0.0266(12) Uani 1 1 d . . .
C52 C 0.3039(3) 0.1753(4) 0.0181(3) 0.0305(13) Uani 1 1 d . . .
H52 H 0.3031 0.1133 0.0254 0.037 Uiso 1 1 calc R . .
C53 C 0.3359(4) 0.1902(6) -0.0423(4) 0.068(3) Uani 1 1 d . . .
H53A H 0.3003 0.1731 -0.0841 0.101 Uiso 1 1 calc R . .
H53B H 0.3811 0.1572 -0.0370 0.101 Uiso 1 1 calc R . .
H53C H 0.3472 0.2499 -0.0450 0.101 Uiso 1 1 calc R . .
C54 C 0.3526(4) 0.2141(5) 0.0828(4) 0.0498(19) Uani 1 1 d . . .
H54A H 0.4005 0.1859 0.0939 0.075 Uiso 1 1 calc R . .
H54B H 0.3291 0.2071 0.1206 0.075 Uiso 1 1 calc R . .
H54C H 0.3595 0.2740 0.0753 0.075 Uiso 1 1 calc R . .
C55 C 0.1128(10) 0.4408(13) 0.4767(12) 0.051(5) Uani 0.50 1 d P A -1
H55A H 0.1118 0.4754 0.4364 0.076 Uiso 0.50 1 calc PR A -1
H55B H 0.1346 0.3861 0.4714 0.076 Uiso 0.50 1 calc PR A -1
H55C H 0.1424 0.4689 0.5173 0.076 Uiso 0.50 1 calc PR A -1
C56 C 0.0339(7) 0.4285(9) 0.4845(7) 0.039(3) Uani 0.50 1 d P A -1
H56A H 0.0037 0.4049 0.4414 0.047 Uiso 0.50 1 calc PR A -1
H56B H 0.0350 0.3865 0.5208 0.047 Uiso 0.50 1 calc PR A -1
C55A C 0.0871(10) 0.4048(12) 0.4777(11) 0.050(5) Uani 0.50 1 d P A -2
H55D H 0.0812 0.3695 0.5157 0.075 Uiso 0.50 1 calc PR A -2
H55E H 0.1386 0.4040 0.4753 0.075 Uiso 0.50 1 calc PR A -2
H55F H 0.0560 0.3832 0.4350 0.075 Uiso 0.50 1 calc PR A -2
C56A C 0.0648(7) 0.4933(9) 0.4887(8) 0.040(3) Uani 0.50 1 d P A -2
H56C H 0.1012 0.5174 0.5279 0.048 Uiso 0.50 1 calc PR A -2
H56D H 0.0662 0.5270 0.4480 0.048 Uiso 0.50 1 calc PR A -2
P1 P 0.14702(8) 0.06619(9) 0.82245(8) 0.0238(3) Uani 1 1 d . . .
F1 F 0.1318(3) 0.1567(2) 0.8391(2) 0.0634(14) Uani 1 1 d . . .
F2 F 0.0840(2) 0.0563(3) 0.7583(2) 0.0626(14) Uani 1 1 d . . .
O1 O 0.2157(2) 0.0646(2) 0.7996(2) 0.0304(9) Uani 1 1 d . . .
O2 O 0.1380(2) 0.0100(2) 0.8764(2) 0.0287(9) Uani 1 1 d . . .
P2 P 0.20788(9) 0.21787(9) 0.35466(8) 0.0263(3) Uani 1 1 d . . .
F3 F 0.1933(4) 0.2776(3) 0.4022(3) 0.0915(18) Uani 1 1 d . . .
F4 F 0.1672(2) 0.1364(2) 0.3590(2) 0.0493(11) Uani 1 1 d . . .
O3 O 0.1943(2) 0.2415(2) 0.2820(2) 0.0327(10) Uani 1 1 d . . .
O4 O 0.2853(3) 0.1812(4) 0.3771(3) 0.0651(17) Uani 1 1 d . . .
N1 N 0.2519(2) 0.2006(2) 0.5863(2) 0.0129(8) Uani 1 1 d . . .
N2 N 0.2751(2) 0.2935(2) 0.6654(2) 0.0160(8) Uani 1 1 d . . .
N3 N 0.2286(2) -0.0031(2) 0.1491(2) 0.0180(9) Uani 1 1 d . . .
N4 N 0.1946(2) 0.0874(2) 0.0695(2) 0.0170(9) Uani 1 1 d . . .
O6 O 0.0000 0.5000 0.5000 0.056(2) Uani 1 2 d S . .
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'
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'
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'
N N 0.0061 0.0033 '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
C1 Au1 O1 175.51(17) . .
C28 Au2 O3 176.28(18) . .
N2 C1 N1 104.7(4) . .
N2 C1 Au1 123.8(3) . .
N1 C1 Au1 131.5(3) . .
C3 C2 N1 107.7(4) . .
C3 C2 H2 126.1 . .
N1 C2 H2 126.1 . .
C2 C3 N2 106.7(4) . .
C2 C3 H3 126.7 . .
N2 C3 H3 126.7 . .
C12 C4 C5 123.0(4) . .
C12 C4 N1 118.1(4) . .
C5 C4 N1 118.7(4) . .
C9 C5 C4 117.5(5) . .
C9 C5 C6 121.5(4) . .
C4 C5 C6 120.9(4) . .
C5 C6 C7 111.4(4) . .
C5 C6 C8 113.5(5) . .
C7 C6 C8 109.3(5) . .
C5 C6 H6 107.5 . .
C7 C6 H6 107.5 . .
C8 C6 H6 107.5 . .
C6 C7 H7A 109.5 . .
C6 C7 H7B 109.5 . .
H7A C7 H7B 109.5 . .
C6 C7 H7C 109.5 . .
H7A C7 H7C 109.5 . .
H7B C7 H7C 109.5 . .
C6 C8 H8A 109.5 . .
C6 C8 H8B 109.5 . .
H8A C8 H8B 109.5 . .
C6 C8 H8C 109.5 . .
H8A C8 H8C 109.5 . .
H8B C8 H8C 109.5 . .
C5 C9 C10 121.0(5) . .
C5 C9 H9 119.5 . .
C10 C9 H9 119.5 . .
C11 C10 C9 120.4(5) . .
C11 C10 H10 119.8 . .
C9 C10 H10 119.8 . .
C10 C11 C12 121.2(5) . .
C10 C11 H11 119.4 . .
C12 C11 H11 119.4 . .
C11 C12 C4 116.9(5) . .
C11 C12 C13 119.4(5) . .
C4 C12 C13 123.7(5) . .
C12 C13 C14 110.6(5) . .
C12 C13 C15 110.7(5) . .
C14 C13 C15 111.4(5) . .
C12 C13 H13 108.0 . .
C14 C13 H13 108.0 . .
C15 C13 H13 108.0 . .
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 . .
C13 C15 H15A 109.5 . .
C13 C15 H15B 109.5 . .
H15A C15 H15B 109.5 . .
C13 C15 H15C 109.5 . .
H15A C15 H15C 109.5 . .
H15B C15 H15C 109.5 . .
C17 C16 C24 123.8(5) . .
C17 C16 N2 118.9(4) . .
C24 C16 N2 117.2(4) . .
C16 C17 C21 116.9(4) . .
C16 C17 C18 122.5(4) . .
C21 C17 C18 120.6(5) . .
C20 C18 C17 110.0(4) . .
C20 C18 C19 111.0(5) . .
C17 C18 C19 111.2(4) . .
C20 C18 H18 108.2 . .
C17 C18 H18 108.2 . .
C19 C18 H18 108.2 . .
C18 C19 H19A 109.5 . .
C18 C19 H19B 109.5 . .
H19A C19 H19B 109.5 . .
C18 C19 H19C 109.5 . .
H19A C19 H19C 109.5 . .
H19B C19 H19C 109.5 . .
C18 C20 H20A 109.5 . .
C18 C20 H20B 109.5 . .
H20A C20 H20B 109.5 . .
C18 C20 H20C 109.5 . .
H20A C20 H20C 109.5 . .
H20B C20 H20C 109.5 . .
C22 C21 C17 121.2(5) . .
C22 C21 H21 119.4 . .
C17 C21 H21 119.4 . .
C21 C22 C23 120.6(5) . .
C21 C22 H22 119.7 . .
C23 C22 H22 119.7 . .
C22 C23 C24 120.6(5) . .
C22 C23 H23 119.7 . .
C24 C23 H23 119.7 . .
C16 C24 C23 116.8(5) . .
C16 C24 C25 123.4(5) . .
C23 C24 C25 119.8(4) . .
C24 C25 C26 110.7(5) . .
C24 C25 C27 111.1(5) . .
C26 C25 C27 111.6(5) . .
C24 C25 H25 107.7 . .
C26 C25 H25 107.7 . .
C27 C25 H25 107.7 . .
C25 C26 H26A 109.5 . .
C25 C26 H26B 109.5 . .
H26A C26 H26B 109.5 . .
C25 C26 H26C 109.5 . .
H26A C26 H26C 109.5 . .
H26B C26 H26C 109.5 . .
C25 C27 H27A 109.5 . .
C25 C27 H27B 109.5 . .
H27A C27 H27B 109.5 . .
C25 C27 H27C 109.5 . .
H27A C27 H27C 109.5 . .
H27B C27 H27C 109.5 . .
N4 C28 N3 105.8(4) . .
N4 C28 Au2 129.3(4) . .
N3 C28 Au2 124.8(4) . .
C30 C29 N3 107.2(4) . .
C30 C29 H29 126.4 . .
N3 C29 H29 126.4 . .
C29 C30 N4 106.2(5) . .
C29 C30 H30 126.9 . .
N4 C30 H30 126.9 . .
C39 C31 C32 123.5(5) . .
C39 C31 N3 118.4(4) . .
C32 C31 N3 118.0(5) . .
C36 C32 C31 115.9(6) . .
C36 C32 C33 122.5(5) . .
C31 C32 C33 121.5(5) . .
C32 C33 C35 113.3(5) . .
C32 C33 C34 109.9(5) . .
C35 C33 C34 111.1(5) . .
C32 C33 H33 107.4 . .
C35 C33 H33 107.4 . .
C34 C33 H33 107.4 . .
C33 C34 H34A 109.5 . .
C33 C34 H34B 109.5 . .
H34A C34 H34B 109.5 . .
C33 C34 H34C 109.5 . .
H34A C34 H34C 109.5 . .
H34B C34 H34C 109.5 . .
C33 C35 H35A 109.5 . .
C33 C35 H35B 109.5 . .
H35A C35 H35B 109.5 . .
C33 C35 H35C 109.5 . .
H35A C35 H35C 109.5 . .
H35B C35 H35C 109.5 . .
C37 C36 C32 122.7(6) . .
C37 C36 H36 118.6 . .
C32 C36 H36 118.6 . .
C36 C37 C38 119.8(6) . .
C36 C37 H37 120.1 . .
C38 C37 H37 120.1 . .
C37 C38 C39 121.0(6) . .
C37 C38 H38 119.5 . .
C39 C38 H38 119.5 . .
C31 C39 C38 117.0(5) . .
C31 C39 C40 122.8(5) . .
C38 C39 C40 120.2(6) . .
C42 C40 C39 112.4(6) . .
C42 C40 C41 111.3(5) . .
C39 C40 C41 109.1(6) . .
C42 C40 H40 107.9 . .
C39 C40 H40 107.9 . .
C41 C40 H40 107.9 . .
C40 C41 H41A 109.5 . .
C40 C41 H41B 109.5 . .
H41A C41 H41B 109.5 . .
C40 C41 H41C 109.5 . .
H41A C41 H41C 109.5 . .
H41B C41 H41C 109.5 . .
C40 C42 H42A 109.5 . .
C40 C42 H42B 109.5 . .
H42A C42 H42B 109.5 . .
C40 C42 H42C 109.5 . .
H42A C42 H42C 109.5 . .
H42B C42 H42C 109.5 . .
C44 C43 C51 123.5(5) . .
C44 C43 N4 118.3(4) . .
C51 C43 N4 118.2(5) . .
C43 C44 C48 116.6(5) . .
C43 C44 C45 124.4(5) . .
C48 C44 C45 119.0(5) . .
C44 C45 C46 110.9(5) . .
C44 C45 C47 112.9(5) . .
C46 C45 C47 110.3(5) . .
C44 C45 H45 107.5 . .
C46 C45 H45 107.5 . .
C47 C45 H45 107.5 . .
C45 C46 H46A 109.5 . .
C45 C46 H46B 109.5 . .
H46A C46 H46B 109.5 . .
C45 C46 H46C 109.5 . .
H46A C46 H46C 109.5 . .
H46B C46 H46C 109.5 . .
C45 C47 H47A 109.5 . .
C45 C47 H47B 109.5 . .
H47A C47 H47B 109.5 . .
C45 C47 H47C 109.5 . .
H47A C47 H47C 109.5 . .
H47B C47 H47C 109.5 . .
C49 C48 C44 121.2(6) . .
C49 C48 H48 119.4 . .
C44 C48 H48 119.4 . .
C50 C49 C48 120.2(6) . .
C50 C49 H49 119.9 . .
C48 C49 H49 119.9 . .
C49 C50 C51 121.2(6) . .
C49 C50 H50 119.4 . .
C51 C50 H50 119.4 . .
C50 C51 C43 117.3(5) . .
C50 C51 C52 121.0(5) . .
C43 C51 C52 121.6(5) . .
C53 C52 C51 112.7(6) . .
C53 C52 C54 110.9(6) . .
C51 C52 C54 110.8(5) . .
C53 C52 H52 107.4 . .
C51 C52 H52 107.4 . .
C54 C52 H52 107.4 . .
C52 C53 H53A 109.5 . .
C52 C53 H53B 109.5 . .
H53A C53 H53B 109.5 . .
C52 C53 H53C 109.5 . .
H53A C53 H53C 109.5 . .
H53B C53 H53C 109.5 . .
C52 C54 H54A 109.5 . .
C52 C54 H54B 109.5 . .
H54A C54 H54B 109.5 . .
C52 C54 H54C 109.5 . .
H54A C54 H54C 109.5 . .
H54B C54 H54C 109.5 . .
O6 C56 C55 115.3(12) . .
O6 C56 H56A 108.5 . .
C55 C56 H56A 108.5 . .
O6 C56 H56B 108.5 . .
C55 C56 H56B 108.5 . .
H56A C56 H56B 107.5 . .
C56A C55A H55D 109.5 . .
C56A C55A H55E 109.5 . .
H55D C55A H55E 109.5 . .
C56A C55A H55F 109.5 . .
H55D C55A H55F 109.5 . .
H55E C55A H55F 109.5 . .
O6 C56A C55A 114.3(12) . .
O6 C56A H56C 108.7 . .
C55A C56A H56C 108.7 . .
O6 C56A H56D 108.7 . .
C55A C56A H56D 108.7 . .
H56C C56A H56D 107.6 . .
O2 P1 O1 119.8(2) . .
O2 P1 F1 110.8(2) . .
O1 P1 F1 108.1(2) . .
O2 P1 F2 111.4(2) . .
O1 P1 F2 106.5(2) . .
F1 P1 F2 97.9(3) . .
P1 O1 Au1 125.0(2) . .
F3 P2 O3 119.1(3) . .
F3 P2 F4 110.4(3) . .
O3 P2 F4 108.0(2) . .
F3 P2 O4 112.3(4) . .
O3 P2 O4 108.2(3) . .
F4 P2 O4 96.4(3) . .
P2 O3 Au2 123.8(2) . .
C1 N1 C2 110.2(4) . .
C1 N1 C4 125.6(4) . .
C2 N1 C4 124.1(4) . .
C1 N2 C3 110.7(4) . .
C1 N2 C16 124.4(4) . .
C3 N2 C16 124.8(4) . .
C28 N3 C29 109.9(4) . .
C28 N3 C31 125.1(4) . .
C29 N3 C31 125.0(4) . .
C28 N4 C30 110.9(4) . .
C28 N4 C43 125.7(4) . .
C30 N4 C43 123.4(4) . .
C56A O6 C56A 179.997(3) . 3_566
C56A O6 C56 127.9(8) . 3_566
C56A O6 C56 52.1(8) 3_566 3_566
C56A O6 C56 52.1(8) . .
C56A O6 C56 127.9(8) 3_566 .
C56 O6 C56 179.998(4) 3_566 .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
Au1 C1 1.947(4) .
Au1 O1 2.048(4) .
Au2 C28 1.951(5) .
Au2 O3 2.039(4) .
C1 N2 1.354(6) .
C1 N1 1.355(6) .
C2 C3 1.325(7) .
C2 N1 1.384(6) .
C2 H2 0.9500 .
C3 N2 1.388(6) .
C3 H3 0.9500 .
C4 C12 1.401(7) .
C4 C5 1.401(6) .
C4 N1 1.445(6) .
C5 C9 1.386(7) .
C5 C6 1.521(7) .
C6 C7 1.523(8) .
C6 C8 1.540(7) .
C6 H6 1.0000 .
C7 H7A 0.9800 .
C7 H7B 0.9800 .
C7 H7C 0.9800 .
C8 H8A 0.9800 .
C8 H8B 0.9800 .
C8 H8C 0.9800 .
C9 C10 1.387(8) .
C9 H9 0.9500 .
C10 C11 1.378(7) .
C10 H10 0.9500 .
C11 C12 1.400(7) .
C11 H11 0.9500 .
C12 C13 1.508(7) .
C13 C14 1.521(8) .
C13 C15 1.526(8) .
C13 H13 1.0000 .
C14 H14A 0.9800 .
C14 H14B 0.9800 .
C14 H14C 0.9800 .
C15 H15A 0.9800 .
C15 H15B 0.9800 .
C15 H15C 0.9800 .
C16 C17 1.389(7) .
C16 C24 1.392(7) .
C16 N2 1.439(6) .
C17 C21 1.391(7) .
C17 C18 1.526(7) .
C18 C20 1.521(7) .
C18 C19 1.530(8) .
C18 H18 1.0000 .
C19 H19A 0.9800 .
C19 H19B 0.9800 .
C19 H19C 0.9800 .
C20 H20A 0.9800 .
C20 H20B 0.9800 .
C20 H20C 0.9800 .
C21 C22 1.374(7) .
C21 H21 0.9500 .
C22 C23 1.381(8) .
C22 H22 0.9500 .
C23 C24 1.400(7) .
C23 H23 0.9500 .
C24 C25 1.517(8) .
C25 C26 1.531(9) .
C25 C27 1.535(8) .
C25 H25 1.0000 .
C26 H26A 0.9800 .
C26 H26B 0.9800 .
C26 H26C 0.9800 .
C27 H27A 0.9800 .
C27 H27B 0.9800 .
C27 H27C 0.9800 .
C28 N4 1.333(6) .
C28 N3 1.350(6) .
C29 C30 1.337(7) .
C29 N3 1.395(7) .
C29 H29 0.9500 .
C30 N4 1.398(6) .
C30 H30 0.9500 .
C31 C39 1.393(8) .
C31 C32 1.403(7) .
C31 N3 1.448(6) .
C32 C36 1.384(8) .
C32 C33 1.506(8) .
C33 C35 1.527(8) .
C33 C34 1.532(8) .
C33 H33 1.0000 .
C34 H34A 0.9800 .
C34 H34B 0.9800 .
C34 H34C 0.9800 .
C35 H35A 0.9800 .
C35 H35B 0.9800 .
C35 H35C 0.9800 .
C36 C37 1.373(10) .
C36 H36 0.9500 .
C37 C38 1.376(9) .
C37 H37 0.9500 .
C38 C39 1.397(8) .
C38 H38 0.9500 .
C39 C40 1.508(8) .
C40 C42 1.504(10) .
C40 C41 1.526(9) .
C40 H40 1.0000 .
C41 H41A 0.9800 .
C41 H41B 0.9800 .
C41 H41C 0.9800 .
C42 H42A 0.9800 .
C42 H42B 0.9800 .
C42 H42C 0.9800 .
C43 C44 1.389(7) .
C43 C51 1.395(7) .
C43 N4 1.445(6) .
C44 C48 1.398(7) .
C44 C45 1.517(8) .
C45 C46 1.518(9) .
C45 C47 1.524(9) .
C45 H45 1.0000 .
C46 H46A 0.9800 .
C46 H46B 0.9800 .
C46 H46C 0.9800 .
C47 H47A 0.9800 .
C47 H47B 0.9800 .
C47 H47C 0.9800 .
C48 C49 1.382(8) .
C48 H48 0.9500 .
C49 C50 1.375(9) .
C49 H49 0.9500 .
C50 C51 1.384(8) .
C50 H50 0.9500 .
C51 C52 1.529(8) .
C52 C53 1.508(8) .
C52 C54 1.532(9) .
C52 H52 1.0000 .
C53 H53A 0.9800 .
C53 H53B 0.9800 .
C53 H53C 0.9800 .
C54 H54A 0.9800 .
C54 H54B 0.9800 .
C54 H54C 0.9800 .
C55 C56 1.540(19) .
C55 H55A 0.9800 .
C55 H55B 0.9800 .
C55 H55C 0.9800 .
C56 O6 1.379(13) .
C56 H56A 0.9900 .
C56 H56B 0.9900 .
C55A C56A 1.50(2) .
C55A H55D 0.9800 .
C55A H55E 0.9800 .
C55A H55F 0.9800 .
C56A O6 1.295(12) .
C56A H56C 0.9900 .
C56A H56D 0.9900 .
P1 O2 1.453(4) .
P1 O1 1.473(4) .
P1 F1 1.524(4) .
P1 F2 1.535(4) .
P2 F3 1.427(5) .
P2 O3 1.479(4) .
P2 F4 1.519(4) .
P2 O4 1.529(5) .
O6 C56A 1.295(12) 3_566
O6 C56 1.379(13) 3_566
