#------------------------------------------------------------------------------
#$Date: 2016-03-22 13:56:23 +0200 (Tue, 22 Mar 2016) $
#$Revision: 178982 $
#$URL: svn://www.crystallography.net/cod/cif/4/12/05/4120593.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_4120593
loop_
_publ_author_name
'Guenther, Johannes'
'Mallet-Ladeira, Sonia'
'Estevez, Laura'
'Miqueu, Karinne'
'Amgoune, Abderrahmane'
'Bourissou, Didier'
_publ_section_title
;
 Activation of Aryl Halides at Gold(I): Practical Synthesis of (P,C)
 Cyclometalated Gold(III) Complexes.
;
_journal_issue                   5
_journal_name_full               'Journal of the American Chemical Society'
_journal_page_first              1778
_journal_page_last               1781
_journal_paper_doi               10.1021/ja412432k
_journal_volume                  136
_journal_year                    2014
_chemical_compound_source        'synthesis as described'
_chemical_formula_moiety         'C22 H16 Au I2 P'
_chemical_formula_sum            'C22 H16 Au I2 P'
_chemical_formula_weight         762.09
_chemical_name_systematic
;
 ?
;
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_Int_Tables_number      14
_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
_cell_angle_alpha                90
_cell_angle_beta                 114.000(2)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   15.3537(6)
_cell_length_b                   9.0513(3)
_cell_length_c                   16.4471(6)
_cell_measurement_reflns_used    9920
_cell_measurement_temperature    193(2)
_cell_measurement_theta_max      33.14
_cell_measurement_theta_min      2.63
_cell_measurement_wavelength     0.71073
_cell_volume                     2088.06(14)
_computing_cell_refinement       'APEX2 and SAINT (Bruker, 2008)'
_computing_data_collection       'APEX2 (Bruker, 2008)'
_computing_data_reduction        'SAINT (Bruker, 2008)'
_computing_molecular_graphics    'Ortep-3 for Windows (Farrugia, 1997)'
_computing_publication_material  'WinGX publication routines (Farrugia, 1999)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      193(2)
_diffrn_measured_fraction_theta_full 0.993
_diffrn_measured_fraction_theta_max 0.993
_diffrn_measurement_device_type  'Bruker Kappa APEX II Quazar'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_radiation_monochromator  'multilayer optics'
_diffrn_radiation_probe          x-ray
_diffrn_radiation_source         'microfocus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0528
_diffrn_reflns_av_unetI/netI     0.0541
_diffrn_reflns_limit_h_max       21
_diffrn_reflns_limit_h_min       -23
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       25
_diffrn_reflns_limit_l_min       -25
_diffrn_reflns_number            25612
_diffrn_reflns_theta_full        33.21
_diffrn_reflns_theta_max         33.21
_diffrn_reflns_theta_min         3.06
_diffrn_standards_decay_%        0
_diffrn_standards_interval_count 0
_diffrn_standards_interval_time  0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    10.083
_exptl_absorpt_correction_T_max  0.133
_exptl_absorpt_correction_T_min  0.025
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(SADABS; Bruker, 2008)'
_exptl_crystal_colour            red
_exptl_crystal_density_diffrn    2.424
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             1392
_exptl_crystal_size_max          0.4
_exptl_crystal_size_mid          0.4
_exptl_crystal_size_min          0.2
_refine_diff_density_max         2.627
_refine_diff_density_min         -4.011
_refine_diff_density_rms         0.273
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.03
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     235
_refine_ls_number_reflns         7949
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.03
_refine_ls_R_factor_all          0.0484
_refine_ls_R_factor_gt           0.0374
_refine_ls_shift/su_max          0.002
_refine_ls_shift/su_mean         0
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0477P)²+0.0513P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0902
_refine_ls_wR_factor_ref         0.0953
_reflns_number_gt                6557
_reflns_number_total             7949
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ja412432k_si_002.cif
_cod_data_source_block           3a
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               4120593
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
C1 C 0.0928(3) 0.9593(5) 0.2080(3) 0.0242(8) Uani 1 1 d .
C2 C 0.0299(4) 1.0466(6) 0.2255(4) 0.0363(11) Uani 1 1 d .
H2 H 0.0519 1.1028 0.2789 0.044 Uiso 1 1 calc R
C3 C -0.0673(4) 1.0553(7) 0.1660(4) 0.0454(15) Uani 1 1 d .
H3 H -0.1086 1.1202 0.179 0.055 Uiso 1 1 calc R
C4 C -0.1020(4) 0.9735(7) 0.0917(4) 0.0427(13) Uani 1 1 d .
H4 H -0.1681 0.9775 0.0542 0.051 Uiso 1 1 calc R
C5 C -0.0408(3) 0.8806(5) 0.0684(3) 0.0278(9) Uani 1 1 d .
C6 C -0.0726(3) 0.7960(6) -0.0106(3) 0.0362(11) Uani 1 1 d .
H6 H -0.1384 0.7972 -0.0494 0.043 Uiso 1 1 calc R
C7 C -0.0121(3) 0.7137(6) -0.0323(3) 0.0362(11) Uani 1 1 d .
H7 H -0.0359 0.6569 -0.0855 0.043 Uiso 1 1 calc R
C8 C 0.0863(3) 0.7109(5) 0.0232(3) 0.0293(9) Uani 1 1 d .
H8 H 0.129 0.6544 0.0072 0.035 Uiso 1 1 calc R
C9 C 0.1192(3) 0.7912(4) 0.1006(3) 0.0203(7) Uani 1 1 d .
C10 C 0.0578(3) 0.8771(4) 0.1263(3) 0.0200(7) Uani 1 1 d .
C11 C 0.2875(3) 0.6229(4) 0.2075(2) 0.0180(7) Uani 1 1 d .
C12 C 0.2264(3) 0.5207(4) 0.2202(3) 0.0255(8) Uani 1 1 d .
H12 H 0.1609 0.5439 0.202 0.031 Uiso 1 1 calc R
C13 C 0.2610(4) 0.3854(5) 0.2592(4) 0.0369(11) Uani 1 1 d .
H13 H 0.2196 0.3164 0.2691 0.044 Uiso 1 1 calc R
C14 C 0.3561(4) 0.3513(4) 0.2836(3) 0.0342(11) Uani 1 1 d .
H14 H 0.3804 0.2593 0.3112 0.041 Uiso 1 1 calc R
C15 C 0.4154(4) 0.4498(4) 0.2680(3) 0.0328(11) Uani 1 1 d .
H15 H 0.4799 0.4233 0.2826 0.039 Uiso 1 1 calc R
C16 C 0.3828(3) 0.5869(5) 0.2315(3) 0.0279(9) Uani 1 1 d .
H16 H 0.425 0.6558 0.2228 0.034 Uiso 1 1 calc R
C17 C 0.3060(3) 0.8970(4) 0.1176(2) 0.0159(6) Uani 1 1 d .
C18 C 0.3296(3) 0.8261(5) 0.0545(3) 0.0255(8) Uani 1 1 d .
H18 H 0.3177 0.7233 0.044 0.031 Uiso 1 1 calc R
C19 C 0.3703(4) 0.9051(6) 0.0070(3) 0.0333(10) Uani 1 1 d .
H19 H 0.3871 0.8558 -0.0356 0.04 Uiso 1 1 calc R
C20 C 0.3870(3) 1.0555(5) 0.0208(3) 0.0295(9) Uani 1 1 d .
H20 H 0.4132 1.1095 -0.0135 0.035 Uiso 1 1 calc R
C21 C 0.3654(3) 1.1266(5) 0.0847(3) 0.0256(8) Uani 1 1 d .
H21 H 0.3789 1.2288 0.096 0.031 Uiso 1 1 calc R
C22 C 0.3243(3) 1.0488(4) 0.1322(3) 0.0185(7) Uani 1 1 d .
H22 H 0.3082 1.0985 0.1751 0.022 Uiso 1 1 calc R
P1 P 0.24275(6) 0.80599(10) 0.17422(6) 0.01557(17) Uani 1 1 d .
I1 I 0.22804(3) 1.07343(3) 0.42793(2) 0.03606(9) Uani 1 1 d .
I2 I 0.42537(2) 0.92204(3) 0.373673(19) 0.02848(7) Uani 1 1 d .
Au1 Au 0.236535(11) 0.940412(14) 0.289259(9) 0.01729(5) 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'
P P 0.1023 0.0942 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
I I -0.4742 1.8119 '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
C2 C1 C10 118.0(4)
C2 C1 Au1 124.8(4)
C10 C1 Au1 117.1(3)
C1 C2 C3 121.5(5)
C1 C2 H2 119.2
C3 C2 H2 119.2
C4 C3 C2 121.1(5)
C4 C3 H3 119.4
C2 C3 H3 119.4
C3 C4 C5 120.7(5)
C3 C4 H4 119.7
C5 C4 H4 119.7
C6 C5 C10 118.7(4)
C6 C5 C4 123.2(4)
C10 C5 C4 118.1(4)
C7 C6 C5 121.7(4)
C7 C6 H6 119.2
C5 C6 H6 119.2
C6 C7 C8 120.7(5)
C6 C7 H7 119.7
C8 C7 H7 119.7
C9 C8 C7 118.9(5)
C9 C8 H8 120.5
C7 C8 H8 120.5
C8 C9 C10 122.1(4)
C8 C9 P1 123.8(3)
C10 C9 P1 114.1(3)
C9 C10 C5 117.9(4)
C9 C10 C1 121.6(4)
C5 C10 C1 120.4(4)
C16 C11 C12 119.8(4)
C16 C11 P1 122.1(3)
C12 C11 P1 117.6(3)
C13 C12 C11 120.2(4)
C13 C12 H12 119.9
C11 C12 H12 119.9
C14 C13 C12 119.4(4)
C14 C13 H13 120.3
C12 C13 H13 120.3
C15 C14 C13 120.3(4)
C15 C14 H14 119.8
C13 C14 H14 119.8
C14 C15 C16 121.0(5)
C14 C15 H15 119.5
C16 C15 H15 119.5
C15 C16 C11 119.2(4)
C15 C16 H16 120.4
C11 C16 H16 120.4
C18 C17 C22 119.1(4)
C18 C17 P1 122.4(3)
C22 C17 P1 118.3(3)
C19 C18 C17 120.0(4)
C19 C18 H18 120
C17 C18 H18 120
C18 C19 C20 120.7(5)
C18 C19 H19 119.7
C20 C19 H19 119.7
C21 C20 C19 119.8(4)
C21 C20 H20 120.1
C19 C20 H20 120.1
C22 C21 C20 120.0(4)
C22 C21 H21 120
C20 C21 H21 120
C21 C22 C17 120.5(4)
C21 C22 H22 119.7
C17 C22 H22 119.7
C11 P1 C9 107.83(17)
C11 P1 C17 111.21(18)
C9 P1 C17 109.32(18)
C11 P1 Au1 112.29(13)
C9 P1 Au1 102.14(14)
C17 P1 Au1 113.49(12)
C1 Au1 P1 84.39(12)
C1 Au1 I1 96.08(12)
P1 Au1 I1 175.06(2)
C1 Au1 I2 172.18(12)
P1 Au1 I2 89.72(2)
I1 Au1 I2 90.228(12)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
C1 C2 1.366(6)
C1 C10 1.436(6)
C1 Au1 2.070(4)
C2 C3 1.415(8)
C2 H2 0.95
C3 C4 1.340(9)
C3 H3 0.95
C4 C5 1.425(8)
C4 H4 0.95
C5 C6 1.413(7)
C5 C10 1.423(6)
C6 C7 1.348(8)
C6 H6 0.95
C7 C8 1.412(6)
C7 H7 0.95
C8 C9 1.371(6)
C8 H8 0.95
C9 C10 1.414(6)
C9 P1 1.793(4)
C11 C16 1.391(6)
C11 C12 1.392(6)
C11 P1 1.792(4)
C12 C13 1.384(6)
C12 H12 0.95
C13 C14 1.383(7)
C13 H13 0.95
C14 C15 1.371(7)
C14 H14 0.95
C15 C16 1.381(6)
C15 H15 0.95
C16 H16 0.95
C17 C18 1.388(6)
C17 C22 1.404(5)
C17 P1 1.796(4)
C18 C19 1.383(7)
C18 H18 0.95
C19 C20 1.387(6)
C19 H19 0.95
C20 C21 1.383(7)
C20 H20 0.95
C21 C22 1.380(6)
C21 H21 0.95
C22 H22 0.95
P1 Au1 2.2839(10)
I1 Au1 2.6288(3)
I2 Au1 2.6621(3)
