#------------------------------------------------------------------------------
#$Date: 2016-03-21 10:37:57 +0200 (Mon, 21 Mar 2016) $
#$Revision: 178660 $
#$URL: svn://www.crystallography.net/cod/cif/4/07/71/4077146.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_4077146
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            'C46 H38 Au Cl O P2'
_chemical_formula_weight         901.12
_chemical_name_systematic
;
 ?
;
_space_group_IT_number           9
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  'C -2yc'
_symmetry_space_group_name_H-M   'C 1 c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary
'isostructural with derivative lacking methoxy group'
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                90.00
_cell_angle_beta                 112.657(3)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   17.1531(11)
_cell_length_b                   15.8402(11)
_cell_length_c                   15.1264(8)
_cell_measurement_reflns_used    6284
_cell_measurement_temperature    133(2)
_cell_measurement_theta_max      28
_cell_measurement_theta_min      2
_cell_volume                     3792.8(4)
_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 1.000
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measurement_device_type  'Siemens 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  0.0278
_diffrn_reflns_av_sigmaI/netI    0.0291
_diffrn_reflns_limit_h_max       24
_diffrn_reflns_limit_h_min       -24
_diffrn_reflns_limit_k_max       22
_diffrn_reflns_limit_k_min       -22
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_number            39743
_diffrn_reflns_theta_full        30.00
_diffrn_reflns_theta_max         30.03
_diffrn_reflns_theta_min         1.82
_exptl_absorpt_coefficient_mu    4.069
_exptl_absorpt_correction_T_max  0.802
_exptl_absorpt_correction_T_min  0.615
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   SADABS
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.578
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       tablet
_exptl_crystal_F_000             1792
_exptl_crystal_size_max          0.25
_exptl_crystal_size_mid          0.18
_exptl_crystal_size_min          0.11
_refine_diff_density_max         0.995
_refine_diff_density_min         -0.320
_refine_diff_density_rms         0.062
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0.433(2)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.982
_refine_ls_hydrogen_treatment    'rigid methyl, others riding'
_refine_ls_matrix_type           full
_refine_ls_number_parameters     462
_refine_ls_number_reflns         10986
_refine_ls_number_restraints     152
_refine_ls_restrained_S_all      0.975
_refine_ls_R_factor_all          0.0201
_refine_ls_R_factor_gt           0.0179
_refine_ls_shift/su_max          0.005
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0170P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0355
_refine_ls_wR_factor_ref         0.0359
_reflns_number_gt                10391
_reflns_number_total             10986
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            om020753p.cif
_cod_data_source_block           noan
_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 (20
times).

'_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 (27 times).

Automatic conversion script
Id: cif_fix_values 1715 2011-07-08 13:25:40Z adriana 
;
_cod_original_sg_symbol_H-M      'C c'
_cod_database_code               4077146
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'x, -y, z+1/2'
'x+1/2, y+1/2, 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
Au Au -0.000868(6) 0.647731(4) 0.751224(6) 0.02126(2) Uani 1 1 d .
Cl Cl -0.06539(6) 0.63455(5) 0.85797(7) 0.03122(19) Uani 1 1 d .
C1 C 0.0539(2) 0.64751(16) 0.6595(3) 0.0237(7) Uani 1 1 d U
C2 C 0.08810(15) 0.63666(13) 0.60449(17) 0.0231(5) Uani 1 1 d U
C3 C 0.12494(14) 0.61798(14) 0.53604(16) 0.0222(4) Uani 1 1 d DU
C4 C 0.19759(15) 0.65953(14) 0.53635(17) 0.0243(5) Uani 1 1 d DU
H4 H 0.2235 0.7018 0.5831 0.029 Uiso 1 1 calc R
C5 C 0.23219(18) 0.63984(16) 0.4694(2) 0.0238(6) Uani 1 1 d DU
H5 H 0.2808 0.6692 0.4703 0.029 Uiso 1 1 calc R
C6 C 0.19615(14) 0.57765(13) 0.40142(16) 0.0217(4) Uani 1 1 d DU
C7 C 0.12321(14) 0.53603(14) 0.39909(15) 0.0235(4) Uani 1 1 d DU
H7 H 0.0976 0.4939 0.3522 0.028 Uiso 1 1 calc R
C8 C 0.08867(14) 0.55650(15) 0.46531(15) 0.0235(4) Uani 1 1 d DU
H8 H 0.0390 0.5281 0.4628 0.028 Uiso 1 1 calc R
O O 0.23668(12) 0.56011(11) 0.34120(13) 0.0269(4) Uani 1 1 d U
C9 C 0.20030(16) 0.49380(15) 0.27282(17) 0.0296(5) Uani 1 1 d U
H9A H 0.1969 0.4420 0.3066 0.035 Uiso 1 1 calc R
H9B H 0.2357 0.4838 0.2362 0.035 Uiso 1 1 calc R
H9C H 0.1435 0.5104 0.2291 0.035 Uiso 1 1 calc R
C10 C 0.60980(13) 0.62402(12) 0.11959(15) 0.0180(4) Uani 1 1 d .
H10 H 0.6108 0.6839 0.1176 0.022 Uiso 1 1 calc R
P1 P 0.51721(3) 0.57801(3) 0.04890(4) 0.01463(10) Uani 1 1 d .
P2 P 0.70105(3) 0.57726(3) 0.19343(4) 0.01484(10) Uani 1 1 d .
C11 C 0.43770(13) 0.58581(12) 0.09982(14) 0.0168(4) Uani 1 1 d DU
C12 C 0.35438(13) 0.55828(14) 0.04996(15) 0.0215(4) Uani 1 1 d DU
H12 H 0.3393 0.5310 -0.0103 0.026 Uiso 1 1 calc R
C13 C 0.29425(14) 0.57100(14) 0.08872(17) 0.0247(5) Uani 1 1 d DU
H13 H 0.2382 0.5512 0.0558 0.030 Uiso 1 1 calc R
C14 C 0.31574(15) 0.61281(14) 0.17603(17) 0.0254(5) Uani 1 1 d DU
H14 H 0.2738 0.6228 0.2014 0.031 Uiso 1 1 calc R
C15 C 0.39792(15) 0.63995(14) 0.22602(16) 0.0251(5) Uani 1 1 d DU
H15 H 0.4126 0.6676 0.2860 0.030 Uiso 1 1 calc R
C16 C 0.45879(14) 0.62634(13) 0.18775(15) 0.0205(4) Uani 1 1 d DU
H16 H 0.5152 0.6448 0.2218 0.025 Uiso 1 1 calc R
C21 C 0.53132(12) 0.46994(12) 0.02226(14) 0.0168(4) Uani 1 1 d DU
C22 C 0.49204(15) 0.40228(14) 0.04710(16) 0.0218(4) Uani 1 1 d DU
H22 H 0.4557 0.4118 0.0803 0.026 Uiso 1 1 calc R
C23 C 0.50647(16) 0.32056(15) 0.02289(19) 0.0310(5) Uani 1 1 d DU
H23 H 0.4794 0.2743 0.0392 0.037 Uiso 1 1 calc R
C24 C 0.55971(15) 0.30611(15) -0.02455(17) 0.0301(5) Uani 1 1 d DU
H24 H 0.5693 0.2501 -0.0404 0.036 Uiso 1 1 calc R
C25 C 0.59929(16) 0.37353(15) -0.04912(17) 0.0265(5) Uani 1 1 d DU
H25 H 0.6361 0.3636 -0.0816 0.032 Uiso 1 1 calc R
C26 C 0.58489(13) 0.45541(14) -0.02611(14) 0.0212(4) Uani 1 1 d DU
H26 H 0.6115 0.5016 -0.0433 0.025 Uiso 1 1 calc R
C31 C 0.47166(13) 0.62945(13) -0.06671(15) 0.0149(4) Uani 1 1 d DU
C32 C 0.48349(13) 0.71635(14) -0.07350(15) 0.0209(4) Uani 1 1 d DU
H32 H 0.5142 0.7479 -0.0174 0.025 Uiso 1 1 calc R
C33 C 0.45069(14) 0.75667(14) -0.16152(16) 0.0248(5) Uani 1 1 d DU
H33 H 0.4590 0.8156 -0.1654 0.030 Uiso 1 1 calc R
C34 C 0.40590(14) 0.71136(14) -0.24378(15) 0.0247(5) Uani 1 1 d DU
H34 H 0.3846 0.7390 -0.3042 0.030 Uiso 1 1 calc R
C35 C 0.39206(15) 0.62535(15) -0.23810(17) 0.0250(5) Uani 1 1 d DU
H35 H 0.3603 0.5945 -0.2944 0.030 Uiso 1 1 calc R
C36 C 0.42475(14) 0.58458(14) -0.15001(15) 0.0213(4) Uani 1 1 d DU
H36 H 0.4152 0.5259 -0.1463 0.026 Uiso 1 1 calc R
C41 C 0.78285(14) 0.58120(14) 0.14566(16) 0.0168(4) Uani 1 1 d DU
C42 C 0.86514(13) 0.55368(13) 0.19856(15) 0.0202(4) Uani 1 1 d DU
H42 H 0.8787 0.5299 0.2603 0.024 Uiso 1 1 calc R
C43 C 0.92712(14) 0.56102(14) 0.16118(16) 0.0242(4) Uani 1 1 d DU
H43 H 0.9829 0.5420 0.1975 0.029 Uiso 1 1 calc R
C44 C 0.90815(14) 0.59612(15) 0.07088(17) 0.0252(5) Uani 1 1 d DU
H44 H 0.9508 0.6011 0.0457 0.030 Uiso 1 1 calc R
C45 C 0.82662(16) 0.62381(15) 0.01785(17) 0.0247(5) Uani 1 1 d DU
H45 H 0.8134 0.6483 -0.0436 0.030 Uiso 1 1 calc R
C46 C 0.76431(16) 0.61567(17) 0.05492(18) 0.0196(5) Uani 1 1 d DU
H46 H 0.7084 0.6338 0.0180 0.023 Uiso 1 1 calc R
C51 C 0.74529(13) 0.63054(12) 0.30831(15) 0.0170(4) Uani 1 1 d DU
C52 C 0.80078(13) 0.58719(13) 0.38881(15) 0.0210(4) Uani 1 1 d DU
H52 H 0.8143 0.5298 0.3833 0.025 Uiso 1 1 calc R
C53 C 0.83580(15) 0.62784(14) 0.47625(16) 0.0257(5) Uani 1 1 d DU
H53 H 0.8733 0.5982 0.5306 0.031 Uiso 1 1 calc R
C54 C 0.81643(15) 0.71187(15) 0.48495(16) 0.0264(5) Uani 1 1 d DU
H54 H 0.8410 0.7398 0.5450 0.032 Uiso 1 1 calc R
C55 C 0.76114(14) 0.75474(14) 0.40573(15) 0.0246(5) Uani 1 1 d DU
H55 H 0.7475 0.8120 0.4120 0.030 Uiso 1 1 calc R
C56 C 0.72552(14) 0.71501(13) 0.31745(15) 0.0208(4) Uani 1 1 d DU
H56 H 0.6879 0.7450 0.2635 0.025 Uiso 1 1 calc R
C61 C 0.68677(12) 0.46917(12) 0.22168(14) 0.0170(4) Uani 1 1 d DU
C62 C 0.63482(13) 0.45450(14) 0.27248(14) 0.0212(4) Uani 1 1 d DU
H62 H 0.6083 0.5006 0.2899 0.025 Uiso 1 1 calc R
C63 C 0.62208(16) 0.37323(15) 0.29724(17) 0.0267(5) Uani 1 1 d DU
H63 H 0.5866 0.3633 0.3314 0.032 Uiso 1 1 calc R
C64 C 0.66174(16) 0.30550(15) 0.27176(17) 0.0310(5) Uani 1 1 d DU
H64 H 0.6532 0.2495 0.2886 0.037 Uiso 1 1 calc R
C65 C 0.71271(16) 0.32008(15) 0.22266(18) 0.0316(5) Uani 1 1 d DU
H65 H 0.7395 0.2738 0.2059 0.038 Uiso 1 1 calc R
C66 C 0.72616(14) 0.40171(13) 0.19666(16) 0.0221(4) Uani 1 1 d DU
H66 H 0.7616 0.4111 0.1625 0.026 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'
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'
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'
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 Cl 174.66(7) y
C2 C1 Au 171.8(2) y
C1 C2 C3 175.5(3) y
C8 C3 C4 117.3(2) y
C8 C3 C2 120.3(2) y
C4 C3 C2 122.4(2) y
C5 C4 C3 121.2(2) y
C6 C5 C4 120.4(3) y
O C6 C5 116.2(2) y
O C6 C7 124.3(2) y
C5 C6 C7 119.4(2) y
C8 C7 C6 119.9(2) y
C7 C8 C3 121.8(2) y
C6 O C9 115.83(19) y
P1 C10 P2 128.77(12) y
C10 P1 C21 112.08(10) y
C10 P1 C11 112.18(10) y
C21 P1 C11 110.44(9) y
C10 P1 C31 111.44(10) y
C21 P1 C31 104.92(9) y
C11 P1 C31 105.34(10) y
C10 P2 C61 113.20(10) y
C10 P2 C41 112.41(11) y
C61 P2 C41 108.91(10) y
C10 P2 C51 111.45(10) y
C61 P2 C51 105.04(9) y
C41 P2 C51 105.29(10) y
C16 C11 C12 119.48(19) ?
C16 C11 P1 118.45(16) ?
C12 C11 P1 121.87(16) ?
C13 C12 C11 119.9(2) ?
C12 C13 C14 120.2(2) ?
C15 C14 C13 120.4(2) ?
C14 C15 C16 119.5(2) ?
C15 C16 C11 120.5(2) ?
C22 C21 C26 119.92(19) ?
C22 C21 P1 123.51(16) ?
C26 C21 P1 116.57(15) ?
C21 C22 C23 119.4(2) ?
C24 C23 C22 120.7(2) ?
C23 C24 C25 120.0(2) ?
C26 C25 C24 119.8(2) ?
C25 C26 C21 120.1(2) ?
C36 C31 C32 118.83(19) ?
C36 C31 P1 121.69(16) ?
C32 C31 P1 119.48(16) ?
C33 C32 C31 120.44(19) ?
C34 C33 C32 120.3(2) ?
C33 C34 C35 120.1(2) ?
C36 C35 C34 119.9(2) ?
C35 C36 C31 120.5(2) ?
C46 C41 C42 118.9(2) ?
C46 C41 P2 119.23(18) ?
C42 C41 P2 121.87(17) ?
C43 C42 C41 120.3(2) ?
C42 C43 C44 120.5(2) ?
C45 C44 C43 119.7(2) ?
C44 C45 C46 119.8(2) ?
C45 C46 C41 120.9(2) ?
C56 C51 C52 119.42(19) ?
C56 C51 P2 120.74(15) ?
C52 C51 P2 119.83(15) ?
C53 C52 C51 120.1(2) ?
C52 C53 C54 120.3(2) ?
C55 C54 C53 119.7(2) ?
C54 C55 C56 120.7(2) ?
C55 C56 C51 119.67(19) ?
C66 C61 C62 119.94(19) ?
C66 C61 P2 122.66(16) ?
C62 C61 P2 117.39(16) ?
C63 C62 C61 120.2(2) ?
C62 C63 C64 119.6(2) ?
C65 C64 C63 120.0(2) ?
C64 C65 C66 121.3(2) ?
C61 C66 C65 119.0(2) ?
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_publ_flag
Au C1 1.952(4) y
Au Cl 2.2917(10) y
C1 C2 1.201(4) y
C2 C3 1.436(4) y
C3 C8 1.403(3) y
C3 C4 1.408(3) y
C4 C5 1.393(4) y
C5 C6 1.385(3) y
C6 O 1.370(3) y
C6 C7 1.403(3) y
C7 C8 1.384(3) y
O C9 1.437(3) y
C10 P1 1.700(2) y
C10 P2 1.703(2) y
P1 C21 1.796(2) y
P1 C11 1.810(2) y
P1 C31 1.811(2) y
P2 C61 1.804(2) y
P2 C41 1.810(2) y
P2 C51 1.814(2) y
C11 C16 1.393(3) ?
C11 C12 1.404(3) ?
C12 C13 1.383(3) ?
C13 C14 1.394(3) ?
C14 C15 1.386(3) ?
C15 C16 1.392(3) ?
C21 C22 1.392(3) ?
C21 C26 1.397(3) ?
C22 C23 1.393(3) ?
C23 C24 1.381(4) ?
C24 C25 1.391(4) ?
C25 C26 1.389(3) ?
C31 C36 1.400(3) ?
C31 C32 1.401(3) ?
C32 C33 1.386(3) ?
C33 C34 1.385(3) ?
C34 C35 1.391(3) ?
C35 C36 1.390(3) ?
C41 C46 1.395(3) ?
C41 C42 1.397(3) ?
C42 C43 1.388(3) ?
C43 C44 1.392(3) ?
C44 C45 1.388(3) ?
C45 C46 1.391(3) ?
C51 C56 1.400(3) ?
C51 C52 1.403(3) ?
C52 C53 1.383(3) ?
C53 C54 1.390(3) ?
C54 C55 1.386(3) ?
C55 C56 1.387(3) ?
C61 C66 1.392(3) ?
C61 C62 1.402(3) ?
C62 C63 1.381(3) ?
C63 C64 1.402(4) ?
C64 C65 1.367(4) ?
C65 C66 1.396(3) ?
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
C7 H7 Au 0.95 2.87 3.787(2) 162.9 2_564
