#------------------------------------------------------------------------------
#$Date: 2016-03-21 14:54:51 +0200 (Mon, 21 Mar 2016) $
#$Revision: 178729 $
#$URL: svn://www.crystallography.net/cod/cif/4/08/40/4084067.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_4084067
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_formula_moiety         'C20 H26 Au N O4 P , Sb F6'
_chemical_formula_sum            'C20 H26 Au F6 N O4 P Sb'
_chemical_formula_weight         808.10
_chemical_name_systematic
;
 ?
;
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2ybc'
_symmetry_space_group_name_H-M   'P 1 21/c 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                 94.626(2)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   8.6591(3)
_cell_length_b                   16.4937(5)
_cell_length_c                   18.0709(6)
_cell_measurement_temperature    200(2)
_cell_volume                     2572.49(15)
_computing_cell_refinement
'Dirax/lsq (Duisenberg & Schreurs, 1989-2000)'
_computing_data_collection       'Collect (Nonius BV, 1997-2000)'
_computing_data_reduction        'EvalCCD (Duisenberg & Schreurs 1990-2000)'
_computing_molecular_graphics    'DIAMOND (Brandenburg, 1999)'
_computing_publication_material  'SHELXL-97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_structure_solution    'SIR92 (Giacovazzo et al, 1993)'
_diffrn_ambient_temperature      200(2)
_diffrn_detector_area_resol_mean 9
_diffrn_measured_fraction_theta_full 0.994
_diffrn_measured_fraction_theta_max 0.994
_diffrn_measurement_device       '95mm CCD camera on κ-goniostat'
_diffrn_measurement_device_type  KappaCCD
_diffrn_measurement_method       CCD
_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  0.0269
_diffrn_reflns_av_sigmaI/netI    0.0258
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       26
_diffrn_reflns_limit_k_min       -26
_diffrn_reflns_limit_l_max       28
_diffrn_reflns_limit_l_min       -29
_diffrn_reflns_number            46134
_diffrn_reflns_theta_full        35.11
_diffrn_reflns_theta_max         35.11
_diffrn_reflns_theta_min         2.26
_diffrn_standards_decay_%        0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    6.878
_exptl_absorpt_correction_T_max  0.4710
_exptl_absorpt_correction_T_min  0.4097
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
; 
R.H. Blessing, Acta Cryst. (1995), A51, 33-38
;
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    2.087
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       plate-like
_exptl_crystal_F_000             1536
_exptl_crystal_size_max          0.14
_exptl_crystal_size_mid          0.14
_exptl_crystal_size_min          0.11
_refine_diff_density_max         3.968
_refine_diff_density_min         -2.109
_refine_diff_density_rms         0.159
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.186
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     314
_refine_ls_number_reflns         11342
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.186
_refine_ls_R_factor_all          0.0536
_refine_ls_R_factor_gt           0.0416
_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)+(0.0185P)²+1.0567P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0908
_refine_ls_wR_factor_ref         0.0945
_reflns_number_gt                9306
_reflns_number_total             11342
_reflns_threshold_expression     >2σ(I)
_cod_data_source_file            om500568q_si_001.cif
_cod_data_source_block           kblf
_cod_depositor_comments
;Adding full bibliography for 4084063--4084067.cif.

The following automatic conversions were performed:

'_exptl_crystal_density_meas' value 'not measured' was changed to '?'
- the value is perceived as not measured.

Automatic conversion script
Id: cif_fix_values 3008 2015-01-20 13:52:24Z robertas 
;
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               4084067
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -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
Au Au 0.146520(18) 0.226270(9) 0.055424(9) 0.02948(4) Uani 1 1 d .
P P 0.32912(13) 0.31653(6) 0.08975(6) 0.0306(2) Uani 1 1 d .
O1 O 0.4068(5) 0.3038(2) 0.1722(2) 0.0503(9) Uani 1 1 d .
H1 H 0.3603 0.2681 0.1928 0.060 Uiso 1 1 calc R
O2 O -0.2195(4) 0.1057(2) -0.14350(19) 0.0423(8) Uani 1 1 d .
O3 O -0.5400(4) -0.1287(2) -0.1078(2) 0.0481(9) Uani 1 1 d .
O4 O -0.1955(4) -0.0241(2) 0.08417(18) 0.0400(7) Uani 1 1 d .
N N -0.0204(4) 0.1438(2) 0.0206(2) 0.0333(7) Uani 1 1 d .
C1 C -0.1085(5) 0.0972(2) -0.0019(2) 0.0299(7) Uani 1 1 d .
C2 C -0.2187(4) 0.0396(2) -0.0305(2) 0.0284(7) Uani 1 1 d .
C3 C -0.2780(5) 0.0448(2) -0.1047(2) 0.0317(8) Uani 1 1 d .
C4 C -0.3879(5) -0.0107(3) -0.1332(3) 0.0346(8) Uani 1 1 d .
H4 H -0.4291 -0.0072 -0.1823 0.040 Uiso 1 1 calc R
C5 C -0.4348(5) -0.0714(3) -0.0867(3) 0.0348(9) Uani 1 1 d .
C6 C -0.3735(5) -0.0792(2) -0.0132(3) 0.0330(8) Uani 1 1 d .
H6 H -0.4055 -0.1211 0.0164 0.040 Uiso 1 1 calc R
C7 C -0.2651(5) -0.0239(2) 0.0147(2) 0.0303(7) Uani 1 1 d .
C8 C -0.2678(8) 0.1130(4) -0.2207(3) 0.0565(15) Uani 1 1 d .
H8A H -0.2457 0.0635 -0.2456 0.050 Uiso 1 1 calc R
H8B H -0.2130 0.1569 -0.2416 0.050 Uiso 1 1 calc R
H8C H -0.3771 0.1236 -0.2267 0.050 Uiso 1 1 calc R
C9 C -0.6205(7) -0.1229(3) -0.1803(3) 0.0532(14) Uani 1 1 d .
H9A H -0.6766 -0.0727 -0.1845 0.050 Uiso 1 1 calc R
H9B H -0.6916 -0.1674 -0.1876 0.050 Uiso 1 1 calc R
H9C H -0.5470 -0.1248 -0.2173 0.050 Uiso 1 1 calc R
C10 C -0.2162(7) -0.0932(3) 0.1295(3) 0.0501(12) Uani 1 1 d .
H10A H -0.3227 -0.0966 0.1404 0.050 Uiso 1 1 calc R
H10B H -0.1515 -0.0882 0.1750 0.050 Uiso 1 1 calc R
H10C H -0.1883 -0.1412 0.1038 0.050 Uiso 1 1 calc R
C11 C 0.4881(5) 0.3110(3) 0.0322(3) 0.0384(10) Uani 1 1 d .
C12 C 0.6405(6) 0.3209(4) 0.0612(4) 0.0567(15) Uani 1 1 d .
H12 H 0.6617 0.3320 0.1115 0.040 Uiso 1 1 calc R
C13 C 0.7591(7) 0.3143(4) 0.0164(6) 0.082(3) Uani 1 1 d .
H13 H 0.8605 0.3215 0.0365 0.040 Uiso 1 1 calc R
C14 C 0.7324(9) 0.2976(4) -0.0565(6) 0.084(3) Uani 1 1 d .
H14 H 0.8148 0.2922 -0.0861 0.040 Uiso 1 1 calc R
C15 C 0.5810(9) 0.2886(4) -0.0872(5) 0.070(2) Uani 1 1 d .
H15 H 0.5617 0.2783 -0.1377 0.040 Uiso 1 1 calc R
C16 C 0.4592(6) 0.2949(3) -0.0428(3) 0.0452(11) Uani 1 1 d .
H16 H 0.3579 0.2884 -0.0632 0.040 Uiso 1 1 calc R
C17 C 0.2619(6) 0.4220(3) 0.0898(3) 0.0391(9) Uani 1 1 d .
C18 C 0.2026(7) 0.4447(3) 0.0106(3) 0.0487(12) Uani 1 1 d .
H18A H 0.1596 0.4984 0.0102 0.050 Uiso 1 1 calc R
H18B H 0.1241 0.4069 -0.0074 0.050 Uiso 1 1 calc R
H18C H 0.2868 0.4432 -0.0208 0.050 Uiso 1 1 calc R
C19 C 0.3943(8) 0.4780(3) 0.1176(4) 0.0678(19) Uani 1 1 d .
H19A H 0.4784 0.4723 0.0864 0.050 Uiso 1 1 calc R
H19B H 0.4291 0.4637 0.1677 0.050 Uiso 1 1 calc R
H19C H 0.3587 0.5331 0.1161 0.050 Uiso 1 1 calc R
C20 C 0.1294(9) 0.4257(4) 0.1407(4) 0.0657(18) Uani 1 1 d .
H20A H 0.0873 0.4795 0.1402 0.050 Uiso 1 1 calc R
H20B H 0.1678 0.4118 0.1904 0.050 Uiso 1 1 calc R
H20C H 0.0499 0.3880 0.1236 0.050 Uiso 1 1 calc R
Sb Sb 0.08822(4) 0.15389(2) 0.275519(18) 0.04239(8) Uani 1 1 d .
F1 F 0.1026(5) 0.2132(3) 0.3642(3) 0.0795(12) Uani 1 1 d .
F2 F -0.0051(5) 0.2415(3) 0.2250(3) 0.0807(13) Uani 1 1 d .
F3 F -0.1054(5) 0.1180(3) 0.2987(2) 0.0762(12) Uani 1 1 d .
F4 F 0.2824(5) 0.1919(4) 0.2535(3) 0.111(2) Uani 1 1 d .
F5 F 0.1878(6) 0.0675(3) 0.3254(2) 0.0800(13) Uani 1 1 d .
F6 F 0.0727(7) 0.0944(4) 0.1890(2) 0.112(2) 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 0.0000 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'
Au Au -2.0133 8.8022 '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'
Sb Sb -0.5866 1.5461 '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'
loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
N Au P 178.29(11)
O1 P C11 104.4(2)
O1 P C17 103.5(2)
C11 P C17 107.9(2)
O1 P Au 114.10(14)
C11 P Au 111.46(16)
C17 P Au 114.63(16)
C3 O2 C8 118.6(4)
C5 O3 C9 118.6(4)
C7 O4 C10 118.0(4)
C1 N Au 176.3(4)
N C1 C2 179.4(5)
C3 C2 C7 120.0(4)
C3 C2 C1 119.6(4)
C7 C2 C1 120.3(4)
O2 C3 C4 125.0(4)
O2 C3 C2 114.8(4)
C4 C3 C2 120.2(4)
C5 C4 C3 118.4(4)
O3 C5 C4 124.0(4)
O3 C5 C6 113.6(4)
C4 C5 C6 122.4(4)
C7 C6 C5 118.9(4)
O4 C7 C6 125.5(4)
O4 C7 C2 114.5(4)
C6 C7 C2 120.0(4)
C16 C11 C12 118.9(5)
C16 C11 P 119.4(4)
C12 C11 P 121.6(5)
C13 C12 C11 120.3(7)
C14 C13 C12 121.3(7)
C13 C14 C15 119.5(6)
C16 C15 C14 120.1(8)
C15 C16 C11 119.8(6)
C19 C17 C18 110.3(5)
C19 C17 C20 111.0(5)
C18 C17 C20 110.0(5)
C19 C17 P 110.1(4)
C18 C17 P 108.4(3)
C20 C17 P 107.0(4)
F6 Sb F3 90.9(3)
F6 Sb F2 89.9(2)
F3 Sb F2 89.7(2)
F6 Sb F5 90.1(2)
F3 Sb F5 92.2(2)
F2 Sb F5 178.2(2)
F6 Sb F4 90.2(3)
F3 Sb F4 178.8(3)
F2 Sb F4 89.8(2)
F5 Sb F4 88.3(2)
F6 Sb F1 179.2(3)
F3 Sb F1 88.4(2)
F2 Sb F1 90.6(2)
F5 Sb F1 89.4(2)
F4 Sb F1 90.5(3)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
Au N 2.046(4)
Au P 2.2233(10)
P O1 1.598(3)
P C11 1.793(5)
P C17 1.834(5)
O2 C3 1.348(5)
O2 C8 1.429(6)
O3 C5 1.346(5)
O3 C9 1.437(7)
O4 C7 1.348(5)
O4 C10 1.424(6)
N C1 1.135(5)
C1 C2 1.414(5)
C2 C3 1.400(6)
C2 C7 1.407(6)
C3 C4 1.389(6)
C4 C5 1.389(7)
C5 C6 1.396(6)
C6 C7 1.375(6)
C11 C16 1.383(8)
C11 C12 1.391(7)
C12 C13 1.362(10)
C13 C14 1.348(13)
C14 C15 1.390(12)
C15 C16 1.379(8)
C17 C19 1.525(7)
C17 C18 1.529(7)
C17 C20 1.529(8)
Sb F6 1.842(4)
Sb F3 1.858(4)
Sb F2 1.858(4)
Sb F5 1.860(4)
Sb F4 1.867(4)
Sb F1 1.873(4)
