#------------------------------------------------------------------------------
#$Date: 2016-03-21 10:37:57 +0200 (Mon, 21 Mar 2016) $
#$Revision: 178660 $
#$URL: svn://www.crystallography.net/cod/cif/4/07/71/4077147.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_4077147
loop_
_publ_author_name
'Vicente, José'
'Singhal, Anshu R.'
'Jones, Peter G.'
_publ_section_title
;
 New Ylide−, Alkynyl−, and Mixed
 Alkynyl/Ylide−Gold(I) Complexes
;
_journal_issue                   26
_journal_name_full               Organometallics
_journal_page_first              5887
_journal_paper_doi               10.1021/om020753p
_journal_volume                  21
_journal_year                    2002
_chemical_formula_sum            'C49 H42 Au N O3 P2'
_chemical_formula_weight         951.74
_chemical_name_systematic
;
 ?
;
_space_group_IT_number           2
_symmetry_cell_setting           triclinic
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                78.828(3)
_cell_angle_beta                 68.060(3)
_cell_angle_gamma                68.627(3)
_cell_formula_units_Z            2
_cell_length_a                   11.7875(11)
_cell_length_b                   13.4391(12)
_cell_length_c                   14.8753(12)
_cell_measurement_reflns_used    7344
_cell_measurement_temperature    133(2)
_cell_measurement_theta_max      30.5
_cell_measurement_theta_min      2.3
_cell_volume                     2030.9(3)
_computing_cell_refinement       'Bruker SAINT'
_computing_data_collection       'Bruker SMART'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'Siemens XP'
_computing_publication_material  SHELXL-97
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      133(2)
_diffrn_detector_area_resol_mean 8.192
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_device_type  'Bruker SMART 1000 CCD'
_diffrn_measurement_method       'ω- & φ-scan'
_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  0.0298
_diffrn_reflns_av_sigmaI/netI    0.0332
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_k_min       -18
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_number            40358
_diffrn_reflns_theta_full        30.00
_diffrn_reflns_theta_max         30.03
_diffrn_reflns_theta_min         1.48
_exptl_absorpt_coefficient_mu    3.745
_exptl_absorpt_correction_T_max  0.802
_exptl_absorpt_correction_T_min  0.608
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   SADABS
_exptl_crystal_colour            orange
_exptl_crystal_density_diffrn    1.556
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       tablet
_exptl_crystal_F_000             952
_exptl_crystal_size_max          0.26
_exptl_crystal_size_mid          0.22
_exptl_crystal_size_min          0.09
_refine_diff_density_max         2.104
_refine_diff_density_min         -1.108
_refine_diff_density_rms         0.103
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.007
_refine_ls_hydrogen_treatment    riding
_refine_ls_matrix_type           full
_refine_ls_number_parameters     505
_refine_ls_number_reflns         11830
_refine_ls_number_restraints     163
_refine_ls_restrained_S_all      1.000
_refine_ls_R_factor_all          0.0301
_refine_ls_R_factor_gt           0.0244
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0350P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0581
_refine_ls_wR_factor_ref         0.0597
_reflns_number_gt                10462
_reflns_number_total             11830
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            om020753p.cif
_cod_data_source_block           soffty
_cod_depositor_comments
;
The following automatic conversions were performed:

'_geom_bond_publ_flag' value 'Y' changed to 'y' according to
/home/saulius/struct/CIF-dictionaries/cif_core.dic dictionary named
'cif_core.dic' version 2.4.1 from 2010-06-29 (21
time).

'_geom_angle_publ_flag' value 'Y' changed to 'y' according to
/home/saulius/struct/CIF-dictionaries/cif_core.dic dictionary named
'cif_core.dic' version 2.4.1 from 2010-06-29 (31 time).

Automatic conversion script
Id: cif_fix_values 1715 2011-07-08 13:25:40Z adriana 
;
_cod_database_code               4077147
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -z'
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
Au Au 0.338677(8) 0.290805(7) 0.428676(6) 0.01973(3) Uani 1 1 d .
P1 P 0.59063(5) 0.30332(5) 0.26169(4) 0.01700(10) Uani 1 1 d .
P2 P 0.38076(5) 0.25354(4) 0.21742(4) 0.01645(10) Uani 1 1 d .
C1 C 0.2544(2) 0.27163(19) 0.57213(17) 0.0224(4) Uani 1 1 d U
C2 C 0.2245(2) 0.2489(2) 0.65662(18) 0.0259(5) Uani 1 1 d U
C3 C 0.2030(2) 0.2093(2) 0.75649(17) 0.0242(5) Uani 1 1 d DU
C4 C 0.2492(2) 0.2423(2) 0.81612(18) 0.0292(5) Uani 1 1 d DU
H4 H 0.2897 0.2960 0.7915 0.035 Uiso 1 1 calc R
C5 C 0.2372(3) 0.1985(2) 0.90924(18) 0.0319(6) Uani 1 1 d DU
H5 H 0.2693 0.2210 0.9489 0.038 Uiso 1 1 calc R
C6 C 0.1769(2) 0.1205(2) 0.94400(17) 0.0279(5) Uani 1 1 d DU
C7 C 0.1301(2) 0.0858(2) 0.88771(18) 0.0280(5) Uani 1 1 d DU
H7 H 0.0902 0.0318 0.9129 0.034 Uiso 1 1 calc R
C8 C 0.1422(2) 0.1305(2) 0.79493(18) 0.0277(5) Uani 1 1 d DU
H8 H 0.1089 0.1080 0.7561 0.033 Uiso 1 1 calc R
N N 0.1612(3) 0.07413(19) 1.04354(17) 0.0395(6) Uani 1 1 d U
O1 O 0.2112(3) 0.0996(2) 1.09029(16) 0.0656(8) Uani 1 1 d U
O2 O 0.1019(2) 0.00956(19) 1.07525(15) 0.0496(6) Uani 1 1 d U
C9 C 0.4423(2) 0.29840(18) 0.28084(15) 0.0188(4) Uani 1 1 d .
C11 C 0.7002(2) 0.18920(18) 0.31013(16) 0.0211(4) Uani 1 1 d DU
C12 C 0.8346(2) 0.1681(2) 0.26859(18) 0.0269(5) Uani 1 1 d DU
H12 H 0.8683 0.2140 0.2165 0.032 Uiso 1 1 calc R
C13 C 0.9183(2) 0.0803(2) 0.3035(2) 0.0319(6) Uani 1 1 d DU
H13 H 1.0089 0.0668 0.2753 0.038 Uiso 1 1 calc R
C14 C 0.8708(3) 0.0130(2) 0.37855(19) 0.0336(6) Uani 1 1 d DU
H14 H 0.9286 -0.0470 0.4018 0.040 Uiso 1 1 calc R
C15 C 0.7395(3) 0.0323(2) 0.42011(18) 0.0323(6) Uani 1 1 d DU
H15 H 0.7070 -0.0145 0.4718 0.039 Uiso 1 1 calc R
C16 C 0.6542(2) 0.12080(19) 0.38625(17) 0.0260(5) Uani 1 1 d DU
H16 H 0.5638 0.1342 0.4157 0.031 Uiso 1 1 calc R
C21 C 0.6895(2) 0.31735(18) 0.13584(16) 0.0198(4) Uani 1 1 d DU
C22 C 0.7439(2) 0.2295(2) 0.07858(17) 0.0245(5) Uani 1 1 d DU
H22 H 0.7296 0.1635 0.1063 0.029 Uiso 1 1 calc R
C23 C 0.8183(2) 0.2379(2) -0.01785(19) 0.0318(6) Uani 1 1 d DU
H23 H 0.8539 0.1783 -0.0566 0.038 Uiso 1 1 calc R
C24 C 0.8408(3) 0.3343(2) -0.0579(2) 0.0389(7) Uani 1 1 d DU
H24 H 0.8925 0.3402 -0.1240 0.047 Uiso 1 1 calc R
C25 C 0.7888(3) 0.4213(2) -0.0024(2) 0.0391(7) Uani 1 1 d DU
H25 H 0.8047 0.4867 -0.0303 0.047 Uiso 1 1 calc R
C26 C 0.7126(2) 0.4132(2) 0.09468(18) 0.0281(5) Uani 1 1 d DU
H26 H 0.6765 0.4734 0.1328 0.034 Uiso 1 1 calc R
C31 C 0.5730(2) 0.41914(18) 0.31809(16) 0.0189(4) Uani 1 1 d DU
C32 C 0.4636(2) 0.50853(19) 0.32337(17) 0.0218(4) Uani 1 1 d DU
H32 H 0.3996 0.5062 0.3004 0.026 Uiso 1 1 calc R
C33 C 0.4474(2) 0.6009(2) 0.36191(18) 0.0256(5) Uani 1 1 d DU
H33 H 0.3726 0.6614 0.3652 0.031 Uiso 1 1 calc R
C34 C 0.5411(2) 0.6043(2) 0.39566(18) 0.0261(5) Uani 1 1 d DU
H34 H 0.5303 0.6673 0.4221 0.031 Uiso 1 1 calc R
C35 C 0.6503(2) 0.5156(2) 0.39064(19) 0.0279(5) Uani 1 1 d DU
H35 H 0.7139 0.5180 0.4141 0.033 Uiso 1 1 calc R
C36 C 0.6666(2) 0.42376(19) 0.35154(17) 0.0241(5) Uani 1 1 d DU
H36 H 0.7421 0.3636 0.3475 0.029 Uiso 1 1 calc R
C41 C 0.4633(2) 0.24500(19) 0.08716(16) 0.0206(4) Uani 1 1 d DU
C42 C 0.5125(2) 0.1489(2) 0.04206(18) 0.0269(5) Uani 1 1 d DU
H42 H 0.5064 0.0843 0.0800 0.032 Uiso 1 1 calc R
C43 C 0.5704(3) 0.1478(2) -0.05851(19) 0.0351(6) Uani 1 1 d DU
H43 H 0.6026 0.0827 -0.0892 0.042 Uiso 1 1 calc R
C44 C 0.5809(3) 0.2416(3) -0.11355(19) 0.0392(7) Uani 1 1 d DU
H44 H 0.6214 0.2404 -0.1820 0.047 Uiso 1 1 calc R
C45 C 0.5331(3) 0.3370(2) -0.06984(19) 0.0351(6) Uani 1 1 d DU
H45 H 0.5409 0.4010 -0.1082 0.042 Uiso 1 1 calc R
C46 C 0.4736(2) 0.3393(2) 0.03005(17) 0.0270(5) Uani 1 1 d DU
H46 H 0.4396 0.4052 0.0599 0.032 Uiso 1 1 calc R
C51 C 0.3669(2) 0.12123(18) 0.26420(15) 0.0187(4) Uani 1 1 d DU
C52 C 0.4737(2) 0.04419(19) 0.28414(18) 0.0252(5) Uani 1 1 d DU
H52 H 0.5495 0.0619 0.2712 0.030 Uiso 1 1 calc R
C53 C 0.4704(2) -0.0577(2) 0.32249(19) 0.0282(5) Uani 1 1 d DU
H53 H 0.5430 -0.1091 0.3368 0.034 Uiso 1 1 calc R
C54 C 0.3604(2) -0.08404(19) 0.33974(18) 0.0266(5) Uani 1 1 d DU
H54 H 0.3582 -0.1541 0.3650 0.032 Uiso 1 1 calc R
C55 C 0.2545(2) -0.0093(2) 0.32054(19) 0.0285(5) Uani 1 1 d DU
H55 H 0.1795 -0.0281 0.3327 0.034 Uiso 1 1 calc R
C56 C 0.2564(2) 0.09380(19) 0.28333(17) 0.0228(5) Uani 1 1 d DU
H56 H 0.1825 0.1454 0.2710 0.027 Uiso 1 1 calc R
C61 C 0.2194(2) 0.34229(18) 0.22175(16) 0.0194(4) Uani 1 1 d DU
C62 C 0.1549(2) 0.42959(19) 0.27965(17) 0.0241(5) Uani 1 1 d DU
H62 H 0.1944 0.4433 0.3190 0.029 Uiso 1 1 calc R
C63 C 0.0329(2) 0.4965(2) 0.2798(2) 0.0311(5) Uani 1 1 d DU
H63 H -0.0107 0.5558 0.3194 0.037 Uiso 1 1 calc R
C64 C -0.0257(2) 0.4771(2) 0.2224(2) 0.0333(6) Uani 1 1 d DU
H64 H -0.1091 0.5230 0.2229 0.040 Uiso 1 1 calc R
C65 C 0.0379(2) 0.3909(2) 0.16462(19) 0.0299(5) Uani 1 1 d DU
H65 H -0.0023 0.3772 0.1257 0.036 Uiso 1 1 calc R
C66 C 0.1602(2) 0.32428(19) 0.16346(17) 0.0233(5) Uani 1 1 d DU
H66 H 0.2040 0.2660 0.1227 0.028 Uiso 1 1 calc R
O91 O -0.14440(18) 0.21555(15) 0.61364(13) 0.0309(4) Uani 1 1 d U
C92 C -0.1087(3) 0.2097(2) 0.5096(2) 0.0326(6) Uani 1 1 d U
H92A H -0.1866 0.2376 0.4897 0.039 Uiso 1 1 calc R
H92B H -0.0628 0.1347 0.4916 0.039 Uiso 1 1 calc R
C93 C -0.0223(3) 0.2769(2) 0.4613(2) 0.0386(6) Uani 1 1 d U
H93A H -0.0314 0.3095 0.3977 0.046 Uiso 1 1 calc R
H93B H 0.0692 0.2341 0.4518 0.046 Uiso 1 1 calc R
C94 C -0.0706(3) 0.3624(2) 0.5333(2) 0.0386(6) Uani 1 1 d U
H94A H -0.1481 0.4208 0.5261 0.046 Uiso 1 1 calc R
H94B H -0.0028 0.3930 0.5262 0.046 Uiso 1 1 calc R
C95 C -0.1027(3) 0.2960(2) 0.6303(2) 0.0321(6) Uani 1 1 d U
H95A H -0.0255 0.2625 0.6508 0.038 Uiso 1 1 calc R
H95B H -0.1721 0.3419 0.6816 0.038 Uiso 1 1 calc R
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'
loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_publ_flag
C1 Au C9 174.36(9) y
C9 P1 C21 116.15(10) y
C9 P1 C31 108.66(10) y
C21 P1 C31 105.76(10) y
C9 P1 C11 117.58(11) y
C21 P1 C11 102.20(10) y
C31 P1 C11 105.39(10) y
C9 P2 C41 118.01(10) y
C9 P2 C51 112.09(11) y
C41 P2 C51 105.82(10) y
C9 P2 C61 111.59(11) y
C41 P2 C61 101.45(10) y
C51 P2 C61 106.85(10) y
C2 C1 Au 168.9(2) y
C1 C2 C3 172.5(3) y
C4 C3 C8 118.2(2) y
C4 C3 C2 121.5(2) y
C8 C3 C2 120.1(2) y
C5 C4 C3 121.5(2) y
C4 C5 C6 118.3(2) y
C7 C6 C5 122.1(2) y
C7 C6 N 118.8(2) y
C5 C6 N 119.1(2) y
C8 C7 C6 119.1(2) y
C7 C8 C3 120.9(2) y
O1 N O2 123.1(2) y
O1 N C6 118.2(2) y
O2 N C6 118.7(2) y
P2 C9 P1 133.64(13) y
P2 C9 Au 110.66(11) y
P1 C9 Au 111.06(11) y
C16 C11 C12 118.4(2) ?
C16 C11 P1 121.59(18) ?
C12 C11 P1 119.98(18) ?
C13 C12 C11 120.3(2) ?
C14 C13 C12 120.4(2) ?
C13 C14 C15 120.2(2) ?
C14 C15 C16 120.0(2) ?
C11 C16 C15 120.7(2) ?
C26 C21 C22 119.1(2) ?
C26 C21 P1 121.69(18) ?
C22 C21 P1 119.23(17) ?
C23 C22 C21 120.7(2) ?
C22 C23 C24 119.5(2) ?
C25 C24 C23 120.6(2) ?
C24 C25 C26 120.0(3) ?
C21 C26 C25 120.2(2) ?
C36 C31 C32 119.1(2) ?
C36 C31 P1 122.80(17) ?
C32 C31 P1 117.98(16) ?
C33 C32 C31 120.6(2) ?
C32 C33 C34 119.7(2) ?
C35 C34 C33 120.0(2) ?
C36 C35 C34 120.2(2) ?
C35 C36 C31 120.3(2) ?
C42 C41 C46 119.1(2) ?
C42 C41 P2 122.50(18) ?
C46 C41 P2 118.33(17) ?
C43 C42 C41 120.1(2) ?
C44 C43 C42 119.9(3) ?
C45 C44 C43 120.6(2) ?
C44 C45 C46 120.0(3) ?
C45 C46 C41 120.3(2) ?
C56 C51 C52 118.8(2) ?
C56 C51 P2 124.20(17) ?
C52 C51 P2 116.97(16) ?
C53 C52 C51 120.9(2) ?
C54 C53 C52 119.4(2) ?
C55 C54 C53 120.4(2) ?
C54 C55 C56 120.4(2) ?
C55 C56 C51 120.0(2) ?
C62 C61 C66 119.0(2) ?
C62 C61 P2 121.77(17) ?
C66 C61 P2 119.18(18) ?
C63 C62 C61 120.1(2) ?
C62 C63 C64 120.4(2) ?
C65 C64 C63 119.9(2) ?
C64 C65 C66 120.1(2) ?
C65 C66 C61 120.5(2) ?
C95 O91 C92 109.12(19) ?
O91 C92 C93 106.4(2) ?
C92 C93 C94 103.0(2) ?
C93 C94 C95 100.8(2) ?
O91 C95 C94 106.2(2) ?
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_publ_flag
Au C1 1.999(2) y
Au C9 2.082(2) y
P1 C9 1.688(2) y
P1 C21 1.814(2) y
P1 C31 1.819(2) y
P1 C11 1.834(2) y
P2 C9 1.682(2) y
P2 C41 1.819(2) y
P2 C51 1.822(2) y
P2 C61 1.824(2) y
C1 C2 1.181(3) y
C2 C3 1.437(3) y
C3 C4 1.403(3) y
C3 C8 1.405(3) y
C4 C5 1.372(3) y
C5 C6 1.390(4) y
C6 C7 1.380(3) y
C6 N 1.462(3) y
C7 C8 1.371(3) y
N O1 1.222(3) y
N O2 1.225(3) y
C11 C16 1.386(3) ?
C11 C12 1.408(3) ?
C12 C13 1.389(3) ?
C13 C14 1.375(4) ?
C14 C15 1.378(4) ?
C15 C16 1.397(3) ?
C21 C26 1.391(3) ?
C21 C22 1.400(3) ?
C22 C23 1.382(3) ?
C23 C24 1.392(4) ?
C24 C25 1.376(4) ?
C25 C26 1.395(3) ?
C31 C36 1.394(3) ?
C31 C32 1.394(3) ?
C32 C33 1.388(3) ?
C33 C34 1.391(3) ?
C34 C35 1.388(4) ?
C35 C36 1.386(3) ?
C41 C42 1.397(3) ?
C41 C46 1.400(3) ?
C42 C43 1.394(3) ?
C43 C44 1.383(4) ?
C44 C45 1.381(4) ?
C45 C46 1.387(3) ?
C51 C56 1.395(3) ?
C51 C52 1.398(3) ?
C52 C53 1.387(3) ?
C53 C54 1.387(3) ?
C54 C55 1.375(3) ?
C55 C56 1.394(3) ?
C61 C62 1.396(3) ?
C61 C66 1.398(3) ?
C62 C63 1.390(3) ?
C63 C64 1.389(4) ?
C64 C65 1.384(4) ?
C65 C66 1.388(3) ?
O91 C95 1.433(3) ?
O91 C92 1.454(3) ?
C92 C93 1.497(4) ?
C93 C94 1.527(4) ?
C94 C95 1.536(4) ?
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
C66 H66 O1 0.95 2.34 3.182(3) 147.0 1_554
C43 H43 O1 0.95 2.62 3.371(4) 135.8 2_656
C23 H23 O2 0.95 2.44 3.301(4) 151.5 2_656
C33 H33 O91 0.95 2.53 3.454(3) 164.6 2_566
C55 H55 O91 0.95 2.62 3.308(3) 129.2 2_556
C7 H7 O2 0.95 2.46 3.254(3) 141.1 2_557
