#------------------------------------------------------------------------------
#$Date: 2016-03-21 13:50:05 +0200 (Mon, 21 Mar 2016) $
#$Revision: 178703 $
#$URL: svn://www.crystallography.net/cod/cif/4/08/14/4081421.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_4081421
loop_
_publ_author_name
'Ghidiu, Michael J.'
'Pistner, Allen J.'
'Yap, Glenn P. A.'
'Lutterman, Daniel A.'
'Rosenthal, Joel'
_publ_section_title
;
 Thermal versus Photochemical Reductive Elimination of Aryl Chlorides from
 NHC--Gold Complexes
;
_journal_issue                   18
_journal_name_full               Organometallics
_journal_page_first              5026
_journal_paper_doi               10.1021/om400701f
_journal_volume                  32
_journal_year                    2013
_chemical_formula_sum            'C33 H36 Au F5 N2'
_chemical_formula_weight         752.60
_chemical_name_systematic
;
 ?
;
_space_group_IT_number           15
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-C 2yc'
_symmetry_space_group_name_H-M   'C 1 2/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                 99.470(2)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   10.8899(16)
_cell_length_b                   20.677(3)
_cell_length_c                   14.218(2)
_cell_measurement_reflns_used    1003
_cell_measurement_temperature    200(2)
_cell_measurement_theta_max      21.08
_cell_measurement_theta_min      2.40
_cell_volume                     3157.8(8)
_computing_cell_refinement       'SAINT (Bruker, 2002)'
_computing_data_collection       'SMART (Bruker, 2002)'
_computing_data_reduction        SAINT
_computing_molecular_graphics    'SHELXTL (Sheldrick, 2001)'
_computing_publication_material  'SHELXTL (Sheldrick, 2001)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      200(2)
_diffrn_detector_area_resol_mean 836.6
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device_type  'Bruker AXS APEX diffractometer'
_diffrn_measurement_method       ω
_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  0.0592
_diffrn_reflns_av_sigmaI/netI    0.0450
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       25
_diffrn_reflns_limit_k_min       -27
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            19482
_diffrn_reflns_theta_full        25.00
_diffrn_reflns_theta_max         28.29
_diffrn_reflns_theta_min         1.97
_diffrn_standards_decay_%        1
_diffrn_standards_interval_count 0
_diffrn_standards_interval_time  0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    4.712
_exptl_absorpt_correction_T_max  0.5882
_exptl_absorpt_correction_T_min  0.3013
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS (Sheldrick, 2003)'
_exptl_crystal_colour            Colorless
_exptl_crystal_density_diffrn    1.583
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       Block
_exptl_crystal_F_000             1488
_exptl_crystal_size_max          0.34
_exptl_crystal_size_mid          0.31
_exptl_crystal_size_min          0.13
_refine_diff_density_max         0.892
_refine_diff_density_min         -0.556
_refine_diff_density_rms         0.103
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.030
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     192
_refine_ls_number_reflns         3926
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.030
_refine_ls_R_factor_all          0.0378
_refine_ls_R_factor_gt           0.0307
_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)+(0.0231P)²+0.0842P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0569
_refine_ls_wR_factor_ref         0.0596
_reflns_number_gt                3493
_reflns_number_total             3926
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            om400701f_si_003.cif
_cod_data_source_block           joer053
_cod_depositor_comments
;
The following automatic conversions were performed:

'_symmetry_cell_setting' value 'Monoclinic' changed to 'monoclinic'
according to /home/saulius/struct/CIF-dictionaries/cif_core.dic
dictionary named 'cif_core.dic' version 2.4.2 from 2011-04-26.

Automatic conversion script
Id: cif_fix_values 1891 2012-01-12 08:04:46Z andrius 
;
_cod_original_cell_volume        3157.7(8)
_cod_original_sg_symbol_H-M      C2/c
_cod_database_code               4081421
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'
'-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 0.0000 0.267295(9) 0.2500 0.03162(7) Uani 1 2 d S
F1 F 0.1914(2) 0.16215(11) 0.19211(15) 0.0560(6) Uani 1 1 d .
F2 F 0.1932(3) 0.03303(13) 0.19584(18) 0.0784(8) Uani 1 1 d .
F3 F 0.0000 -0.03324(16) 0.2500 0.0831(12) Uani 1 2 d S
N1 N 0.0265(2) 0.40528(13) 0.32590(18) 0.0309(6) Uani 1 1 d .
C1 C 0.0000 0.3649(2) 0.2500 0.0285(10) Uani 1 2 d S
C2 C 0.0164(3) 0.46926(17) 0.2979(2) 0.0374(8) Uani 1 1 d .
H2A H 0.0299 0.5061 0.3382 0.045 Uiso 1 1 calc R
C3 C 0.1699(3) 0.37464(17) 0.4702(2) 0.0398(8) Uani 1 1 d .
C4 C 0.1841(4) 0.3563(2) 0.5658(3) 0.0538(11) Uani 1 1 d .
H4A H 0.2653 0.3492 0.6003 0.065 Uiso 1 1 calc R
C5 C 0.0821(4) 0.3482(2) 0.6114(3) 0.0573(11) Uani 1 1 d .
H5A H 0.0946 0.3362 0.6768 0.069 Uiso 1 1 calc R
C6 C -0.0364(4) 0.3574(2) 0.5636(3) 0.0536(11) Uani 1 1 d .
H6A H -0.1052 0.3517 0.5962 0.064 Uiso 1 1 calc R
C7 C -0.0570(3) 0.37487(18) 0.4679(2) 0.0416(9) Uani 1 1 d .
C8 C 0.0474(3) 0.38387(16) 0.4244(2) 0.0332(7) Uani 1 1 d .
C9 C 0.2808(3) 0.3813(2) 0.4189(3) 0.0472(10) Uani 1 1 d .
H9A H 0.2558 0.4106 0.3631 0.057 Uiso 1 1 calc R
C10 C 0.3149(4) 0.3164(3) 0.3805(4) 0.0782(16) Uani 1 1 d .
H10A H 0.2424 0.2984 0.3387 0.117 Uiso 1 1 calc R
H10B H 0.3411 0.2867 0.4338 0.117 Uiso 1 1 calc R
H10C H 0.3832 0.3222 0.3442 0.117 Uiso 1 1 calc R
C11 C 0.3961(4) 0.4101(2) 0.4796(3) 0.0657(13) Uani 1 1 d .
H11A H 0.3738 0.4507 0.5084 0.099 Uiso 1 1 calc R
H11B H 0.4593 0.4188 0.4395 0.099 Uiso 1 1 calc R
H11C H 0.4294 0.3796 0.5301 0.099 Uiso 1 1 calc R
C12 C -0.1883(3) 0.3852(2) 0.4147(3) 0.0493(10) Uani 1 1 d .
H12A H -0.1823 0.3931 0.3462 0.059 Uiso 1 1 calc R
C13 C -0.2703(4) 0.3261(2) 0.4189(4) 0.0719(13) Uani 1 1 d .
H13A H -0.2279 0.2878 0.3995 0.108 Uiso 1 1 calc R
H13B H -0.3493 0.3322 0.3756 0.108 Uiso 1 1 calc R
H13C H -0.2865 0.3204 0.4841 0.108 Uiso 1 1 calc R
C14 C -0.2453(4) 0.4453(2) 0.4520(4) 0.0731(14) Uani 1 1 d .
H14A H -0.3271 0.4535 0.4136 0.110 Uiso 1 1 calc R
H14B H -0.1908 0.4825 0.4476 0.110 Uiso 1 1 calc R
H14C H -0.2547 0.4386 0.5186 0.110 Uiso 1 1 calc R
C15 C 0.0938(3) 0.13185(18) 0.2216(2) 0.0401(8) Uani 1 1 d .
C16 C 0.0973(4) 0.06536(19) 0.2220(3) 0.0490(10) Uani 1 1 d .
C17 C 0.0000 0.0323(3) 0.2500 0.0543(16) Uani 1 2 d S
C33 C 0.0000 0.1696(2) 0.2500 0.0339(11) Uani 1 2 d S
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'
F F 0.0171 0.0103 '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
C1 Au C33 180.0 . .
C1 N1 C2 111.3(3) . .
C1 N1 C8 124.0(3) . .
C2 N1 C8 124.3(3) . .
N1 C1 N1 104.0(4) . 2
N1 C1 Au 127.98(19) . .
N1 C1 Au 127.98(19) 2 .
C2 C2 N1 106.63(18) 2 .
C4 C3 C8 115.8(3) . .
C4 C3 C9 121.7(3) . .
C8 C3 C9 122.5(3) . .
C5 C4 C3 121.4(4) . .
C6 C5 C4 120.9(4) . .
C5 C6 C7 120.6(4) . .
C6 C7 C8 117.2(3) . .
C6 C7 C12 120.8(3) . .
C8 C7 C12 122.0(3) . .
C7 C8 C3 124.0(3) . .
C7 C8 N1 117.4(3) . .
C3 C8 N1 118.6(3) . .
C3 C9 C10 110.8(3) . .
C3 C9 C11 114.2(3) . .
C10 C9 C11 108.8(3) . .
C7 C12 C13 112.2(3) . .
C7 C12 C14 110.2(3) . .
C13 C12 C14 111.5(4) . .
F1 C15 C16 116.1(3) . .
F1 C15 C33 118.6(3) . .
C16 C15 C33 125.3(4) . .
F2 C16 C17 120.3(4) . .
F2 C16 C15 121.2(4) . .
C17 C16 C15 118.5(4) . .
F3 C17 C16 119.8(3) . 2
F3 C17 C16 119.9(3) . .
C16 C17 C16 120.3(5) 2 .
C15 C33 C15 112.1(5) . 2
C15 C33 Au 123.9(2) . .
C15 C33 Au 123.9(2) 2 .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
Au C1 2.018(4) .
Au C33 2.021(5) .
F1 C15 1.358(4) .
F2 C16 1.343(4) .
F3 C17 1.355(6) .
N1 C1 1.358(4) .
N1 C2 1.381(4) .
N1 C8 1.450(4) .
C1 N1 1.358(4) 2
C2 C2 1.350(6) 2
C3 C4 1.394(5) .
C3 C8 1.399(5) .
C3 C9 1.516(5) .
C4 C5 1.385(6) .
C5 C6 1.369(5) .
C6 C7 1.390(5) .
C7 C8 1.394(5) .
C7 C12 1.519(5) .
C9 C10 1.517(6) .
C9 C11 1.524(5) .
C12 C13 1.520(6) .
C12 C14 1.522(6) .
C15 C16 1.375(5) .
C15 C33 1.397(4) .
C16 C17 1.374(5) .
C17 C16 1.374(5) 2
C33 C15 1.397(4) 2
loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_4
C2 N1 C1 N1 0.16(16) 2
C8 N1 C1 N1 173.0(3) 2
C2 N1 C1 Au -179.84(16) .
C8 N1 C1 Au -7.0(3) .
C33 Au C1 N1 96(100) .
C33 Au C1 N1 -84(100) 2
C1 N1 C2 C2 -0.4(4) 2
C8 N1 C2 C2 -173.3(3) 2
C8 C3 C4 C5 -0.3(6) .
C9 C3 C4 C5 -177.8(4) .
C3 C4 C5 C6 0.7(7) .
C4 C5 C6 C7 0.1(7) .
C5 C6 C7 C8 -1.3(6) .
C5 C6 C7 C12 -179.8(4) .
C6 C7 C8 C3 1.8(5) .
C12 C7 C8 C3 -179.7(4) .
C6 C7 C8 N1 -177.0(3) .
C12 C7 C8 N1 1.5(5) .
C4 C3 C8 C7 -1.0(5) .
C9 C3 C8 C7 176.5(3) .
C4 C3 C8 N1 177.8(3) .
C9 C3 C8 N1 -4.7(5) .
C1 N1 C8 C7 -84.7(4) .
C2 N1 C8 C7 87.3(4) .
C1 N1 C8 C3 96.4(3) .
C2 N1 C8 C3 -91.6(4) .
C4 C3 C9 C10 84.9(5) .
C8 C3 C9 C10 -92.5(4) .
C4 C3 C9 C11 -38.3(5) .
C8 C3 C9 C11 144.3(4) .
C6 C7 C12 C13 -56.5(5) .
C8 C7 C12 C13 125.1(4) .
C6 C7 C12 C14 68.5(5) .
C8 C7 C12 C14 -109.9(4) .
F1 C15 C16 F2 0.9(5) .
C33 C15 C16 F2 -178.1(3) .
F1 C15 C16 C17 -179.2(3) .
C33 C15 C16 C17 1.8(5) .
F2 C16 C17 F3 -0.9(4) .
C15 C16 C17 F3 179.2(2) .
F2 C16 C17 C16 179.1(4) 2
C15 C16 C17 C16 -0.8(2) 2
F1 C15 C33 C15 -179.9(3) 2
C16 C15 C33 C15 -0.9(2) 2
F1 C15 C33 Au 0.1(3) .
C16 C15 C33 Au 179.1(2) .
C1 Au C33 C15 160(100) .
C1 Au C33 C15 -20(100) 2
