#------------------------------------------------------------------------------
#$Date: 2016-02-16 22:30:59 +0200 (Tue, 16 Feb 2016) $
#$Revision: 176467 $
#$URL: svn://www.crystallography.net/cod/cif/4/08/40/4084066.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_4084066
loop_
_publ_author_name
'Schröder, Felix'
'Tugny, Coralie'
'Salanouve, Elise'
'Clavier, Hervé'
'Giordano, Laurent'
'Moraleda, Delphine'
'Gimbert, Yves'
'Mouriès-Mansuy, Virginie'
'Goddard, Jean-Philippe'
'Fensterbank, Louis'
_publ_section_title
;
 Secondary Phosphine Oxide--Gold(I) Complexes and Their First Application
 in Catalysis
;
_journal_issue                   15
_journal_name_full               Organometallics
_journal_page_first              4051
_journal_paper_doi               10.1021/om500568q
_journal_volume                  33
_journal_year                    2014
_chemical_compound_source        'synthesis as described'
_chemical_formula_moiety         'C12 H17 Au1 Cl1 O1 P1'
_chemical_formula_sum            'C12 H17 Au Cl O P'
_chemical_formula_weight         440.64
_chemical_name_systematic
;
 ?
;
_space_group_IT_number           61
_symmetry_cell_setting           orthorhombic
_symmetry_Int_Tables_number      61
_symmetry_space_group_name_Hall  '-P 2ac 2ab'
_symmetry_space_group_name_H-M   'P b c a'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_conform_dict_location     ftp://ftp.iucr.org/pub/cif_core.dic
_audit_conform_dict_name         cif_core.dic
_audit_conform_dict_version      2.4
_audit_creation_date             2013-03-26T10:18:33-00:00
_audit_creation_method           'WinGX routine CIF_UPDATE'
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   6.3972(1)
_cell_length_b                   19.2951(4)
_cell_length_c                   21.8976(6)
_cell_measurement_reflns_used    32727
_cell_measurement_temperature    203(2)
_cell_measurement_theta_max      28.11
_cell_measurement_theta_min      2.81
_cell_measurement_wavelength     0.71073
_cell_volume                     2702.92(10)
_computing_molecular_graphics    'Ortep-3 for Windows (Farrugia, 1997)'
_computing_publication_material  'WinGX publication routines (Farrugia, 1999)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      203(2)
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.987
_diffrn_measurement_device_type  KappaCCD
_diffrn_measurement_method       'Omega + Phi scan'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0635
_diffrn_reflns_av_unetI/netI     0.0333
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       25
_diffrn_reflns_limit_k_min       -21
_diffrn_reflns_limit_l_max       28
_diffrn_reflns_limit_l_min       -25
_diffrn_reflns_number            30097
_diffrn_reflns_theta_full        25
_diffrn_reflns_theta_max         28.11
_diffrn_reflns_theta_min         2.81
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    11.179
_exptl_absorpt_correction_T_max  0.49
_exptl_absorpt_correction_T_min  0.3425
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
        [c.f. r.h. blessing, acta cryst. (1995), a51, 33-38]
;
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    2.166
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             1664
_exptl_crystal_size_max          0.14
_exptl_crystal_size_mid          0.1
_exptl_crystal_size_min          0.025
_refine_diff_density_max         1.567
_refine_diff_density_min         -2.038
_refine_diff_density_rms         0.181
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.071
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     146
_refine_ls_number_reflns         3268
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.071
_refine_ls_R_factor_all          0.05
_refine_ls_R_factor_gt           0.0343
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0438P)²+5.5034P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0789
_refine_ls_wR_factor_ref         0.0843
_reflns_number_gt                2634
_reflns_number_total             3268
_reflns_threshold_expression     >2σ(I)
_cod_data_source_file            om500568q_si_001.cif
_cod_data_source_block           hc6-167
_cod_depositor_comments
'Adding full bibliography for 4084063--4084067.cif.'
_cod_original_formula_sum        'C12 H17 Au1 Cl1 O1 P1'
_cod_database_code               4084066
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'x+1/2, -y+1/2, -z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, y, -z-1/2'
'-x-1/2, y-1/2, z'
'x, -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
C1 C 0.2864(9) -0.0188(3) 0.3378(2) 0.0287(11) Uani 1 1 d .
C2 C 0.4126(10) -0.0747(3) 0.3529(3) 0.0371(13) Uani 1 1 d .
H2 H 0.5463 -0.0671 0.3682 0.044 Uiso 1 1 calc R
C3 C 0.3386(11) -0.1425(3) 0.3451(4) 0.0451(17) Uani 1 1 d .
H3 H 0.4224 -0.18 0.3555 0.054 Uiso 1 1 calc R
C4 C 0.1424(10) -0.1530(3) 0.3221(3) 0.0430(15) Uani 1 1 d .
H4 H 0.0942 -0.198 0.3167 0.052 Uiso 1 1 calc R
C5 C 0.0145(10) -0.0981(3) 0.3066(3) 0.0390(13) Uani 1 1 d .
H5 H -0.1187 -0.1061 0.2911 0.047 Uiso 1 1 calc R
C6 C 0.0873(9) -0.0310(3) 0.3146(3) 0.0354(12) Uani 1 1 d .
H6 H 0.0021 0.0063 0.3043 0.042 Uiso 1 1 calc R
C7 C 0.2285(9) 0.1039(3) 0.4110(3) 0.0299(11) Uani 1 1 d .
H7 H 0.0801 0.1025 0.4 0.036 Uiso 1 1 calc R
C8 C 0.2527(10) 0.0615(3) 0.4694(3) 0.0375(13) Uani 1 1 d .
H8A H 0.209 0.0141 0.462 0.045 Uiso 1 1 calc R
H8B H 0.3984 0.0608 0.4816 0.045 Uiso 1 1 calc R
C9 C 0.1210(11) 0.0925(3) 0.5206(3) 0.0485(16) Uani 1 1 d .
H9A H 0.1423 0.066 0.5577 0.058 Uiso 1 1 calc R
H9B H -0.0257 0.0895 0.5098 0.058 Uiso 1 1 calc R
C10 C 0.1794(10) 0.1681(3) 0.5320(3) 0.0458(16) Uani 1 1 d .
H10A H 0.0895 0.1872 0.5634 0.055 Uiso 1 1 calc R
H10B H 0.3226 0.1707 0.5463 0.055 Uiso 1 1 calc R
C11 C 0.1566(10) 0.2102(3) 0.4742(3) 0.0403(14) Uani 1 1 d .
H11A H 0.2019 0.2574 0.482 0.048 Uiso 1 1 calc R
H11B H 0.0105 0.2116 0.4625 0.048 Uiso 1 1 calc R
C12 C 0.2845(9) 0.1801(3) 0.4218(3) 0.0331(12) Uani 1 1 d .
H12A H 0.4322 0.1839 0.4312 0.04 Uiso 1 1 calc R
H12B H 0.2577 0.2064 0.3849 0.04 Uiso 1 1 calc R
O1 O 0.6078(6) 0.0609(2) 0.3702(2) 0.0368(9) Uani 1 1 d .
H1 H 0.6792 0.0929 0.357 0.055 Uiso 1 1 calc R
P1 P 0.3724(2) 0.06961(7) 0.34681(7) 0.0273(3) Uani 1 1 d .
Cl1 Cl 0.3119(2) 0.19919(7) 0.17356(7) 0.0362(3) Uani 1 1 d .
Au1 Au 0.34147(3) 0.134022(10) 0.262321(10) 0.02701(9) Uani 1 1 d .
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 0 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.006 '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_site_symmetry_1
_geom_angle_site_symmetry_3
C2 C1 C6 119.3(5) . .
C2 C1 P1 122.1(4) . .
C6 C1 P1 118.6(4) . .
C1 C2 C3 120.0(6) . .
C1 C2 H2 120 . .
C3 C2 H2 120 . .
C4 C3 C2 119.6(6) . .
C4 C3 H3 120.2 . .
C2 C3 H3 120.2 . .
C3 C4 C5 121.4(6) . .
C3 C4 H4 119.3 . .
C5 C4 H4 119.3 . .
C4 C5 C6 119.1(6) . .
C4 C5 H5 120.4 . .
C6 C5 H5 120.4 . .
C5 C6 C1 120.7(5) . .
C5 C6 H6 119.7 . .
C1 C6 H6 119.7 . .
C8 C7 C12 111.2(5) . .
C8 C7 P1 113.9(4) . .
C12 C7 P1 110.6(4) . .
C8 C7 H7 106.9 . .
C12 C7 H7 106.9 . .
P1 C7 H7 106.9 . .
C9 C8 C7 110.5(5) . .
C9 C8 H8A 109.5 . .
C7 C8 H8A 109.5 . .
C9 C8 H8B 109.5 . .
C7 C8 H8B 109.5 . .
H8A C8 H8B 108.1 . .
C8 C9 C10 111.1(5) . .
C8 C9 H9A 109.4 . .
C10 C9 H9A 109.4 . .
C8 C9 H9B 109.4 . .
C10 C9 H9B 109.4 . .
H9A C9 H9B 108 . .
C11 C10 C9 110.7(5) . .
C11 C10 H10A 109.5 . .
C9 C10 H10A 109.5 . .
C11 C10 H10B 109.5 . .
C9 C10 H10B 109.5 . .
H10A C10 H10B 108.1 . .
C10 C11 C12 112.0(5) . .
C10 C11 H11A 109.2 . .
C12 C11 H11A 109.2 . .
C10 C11 H11B 109.2 . .
C12 C11 H11B 109.2 . .
H11A C11 H11B 107.9 . .
C11 C12 C7 110.9(5) . .
C11 C12 H12A 109.5 . .
C7 C12 H12A 109.5 . .
C11 C12 H12B 109.5 . .
C7 C12 H12B 109.5 . .
H12A C12 H12B 108.1 . .
P1 O1 H1 109.5 . .
O1 P1 C1 102.9(2) . .
O1 P1 C7 105.6(3) . .
C1 P1 C7 106.0(2) . .
O1 P1 Au1 113.98(16) . .
C1 P1 Au1 114.07(18) . .
C7 P1 Au1 113.29(18) . .
P1 Au1 Cl1 178.93(5) . .
P1 Au1 Au1 102.99(4) . 6_556
Cl1 Au1 Au1 77.32(3) . 6_556
P1 Au1 Au1 92.88(3) . 6_656
Cl1 Au1 Au1 86.63(3) . 6_656
Au1 Au1 Au1 160.849(15) 6_556 6_656
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
C1 C2 1.386(8) .
C1 C6 1.392(8) .
C1 P1 1.804(5) .
C2 C3 1.402(8) .
C2 H2 0.93 .
C3 C4 1.368(9) .
C3 H3 0.93 .
C4 C5 1.379(9) .
C4 H4 0.93 .
C5 C6 1.388(8) .
C5 H5 0.93 .
C6 H6 0.93 .
C7 C8 1.525(8) .
C7 C12 1.532(7) .
C7 P1 1.807(6) .
C7 H7 0.98 .
C8 C9 1.524(9) .
C8 H8A 0.97 .
C8 H8B 0.97 .
C9 C10 1.526(9) .
C9 H9A 0.97 .
C9 H9B 0.97 .
C10 C11 1.510(9) .
C10 H10A 0.97 .
C10 H10B 0.97 .
C11 C12 1.524(8) .
C11 H11A 0.97 .
C11 H11B 0.97 .
C12 H12A 0.97 .
C12 H12B 0.97 .
O1 P1 1.599(4) .
O1 H1 0.82 .
P1 Au1 2.2376(14) .
Cl1 Au1 2.3227(14) .
Au1 Au1 3.2438 6_556
Au1 Au1 3.2438 6_656
