#------------------------------------------------------------------------------
#$Date: 2019-11-28 17:49:38 +0200 (Thu, 28 Nov 2019) $
#$Revision: 244213 $
#$URL: file:///home/coder/svn-repositories/cod/cif/1/55/63/1556322.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_1556322
loop_
_publ_author_name
'O'Neill, James A. T.'
'Rosair, Georgina M.'
'Lee, Ai-Lan'
_publ_section_title
;
 Gold(iii)--oxo complexes as catalysts in intramolecular hydroamination
;
_journal_issue                   9
_journal_name_full               'Catalysis Science & Technology'
_journal_page_first              1818
_journal_paper_doi               10.1039/c2cy20255g
_journal_volume                  2
_journal_year                    2012
_chemical_formula_moiety         'C12 H13 N2, Au Cl4'
_chemical_formula_sum            'C12 H13 Au Cl4 N2'
_chemical_formula_weight         524.01
_space_group_IT_number           15
_space_group_name_Hall           '-C 2yc'
_space_group_name_H-M_alt        'C 1 2/c 1'
_symmetry_cell_setting           monoclinic
_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
_audit_update_record
;
2012-04-12 # Formatted by publCIF
;
_cell_angle_alpha                90.00
_cell_angle_beta                 99.676(2)
_cell_angle_gamma                90.00
_cell_formula_units_Z            8
_cell_length_a                   22.1175(10)
_cell_length_b                   14.7910(7)
_cell_length_c                   9.5257(4)
_cell_measurement_reflns_used    9980
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      32.12
_cell_measurement_theta_min      2.61
_cell_volume                     3071.9(2)
_computing_cell_refinement       'Bruker SAINT'
_computing_data_collection       'Bruker APEX2'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      100(2)
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.989
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_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  0.0574
_diffrn_reflns_av_sigmaI/netI    0.0370
_diffrn_reflns_limit_h_max       33
_diffrn_reflns_limit_h_min       -33
_diffrn_reflns_limit_k_max       22
_diffrn_reflns_limit_k_min       -22
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            40918
_diffrn_reflns_theta_full        25.00
_diffrn_reflns_theta_max         32.84
_diffrn_reflns_theta_min         2.75
_exptl_absorpt_coefficient_mu    10.260
_exptl_absorpt_correction_T_max  0.4941
_exptl_absorpt_correction_T_min  0.1921
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS (Bruker, 2008)'
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    2.266
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       BLOCK
_exptl_crystal_F_000             1968
_exptl_crystal_size_max          0.24
_exptl_crystal_size_mid          0.12
_exptl_crystal_size_min          0.08
_refine_diff_density_max         2.160
_refine_diff_density_min         -3.005
_refine_diff_density_rms         0.219
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.016
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     179
_refine_ls_number_reflns         5667
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.016
_refine_ls_R_factor_all          0.0356
_refine_ls_R_factor_gt           0.0275
_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)+(0.0350P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0615
_refine_ls_wR_factor_ref         0.0649
_reflns_number_gt                4911
_reflns_number_total             5667
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            c2cy20255g.txt
_cod_data_source_block           4256
_cod_original_sg_symbol_H-M      C2/c
_cod_database_code               1556322
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
Au1 Au 0.0000 0.208015(10) 0.7500 0.01017(4) Uani 1 2 d S
Cl1 Cl 0.01246(4) 0.31543(5) 0.58542(8) 0.01908(15) Uani 1 1 d .
Cl2 Cl 0.00954(4) 0.09930(5) 0.58575(8) 0.01777(15) Uani 1 1 d .
Au2 Au 0.2500 0.2500 1.0000 0.01197(4) Uani 1 2 d S
Cl3 Cl 0.14995(4) 0.20535(6) 0.94656(9) 0.02066(16) Uani 1 1 d .
Cl4 Cl 0.25391(4) 0.19809(6) 1.22731(8) 0.02152(16) Uani 1 1 d .
N1 N 0.15698(12) 0.38392(19) 0.4573(3) 0.0152(5) Uani 1 1 d .
N2 N 0.14796(12) 0.20592(18) 0.4723(3) 0.0130(5) Uani 1 1 d .
H2 H 0.1651(18) 0.240(3) 0.535(4) 0.016 Uiso 1 1 d .
C2 C 0.15860(15) 0.4746(2) 0.4643(3) 0.0178(6) Uani 1 1 d .
C3 C 0.11998(15) 0.5286(2) 0.3680(4) 0.0226(7) Uani 1 1 d .
H3 H 0.1214 0.5926 0.3765 0.027 Uiso 1 1 calc R
C4 C 0.07979(17) 0.4880(3) 0.2607(4) 0.0269(8) Uani 1 1 d .
H4 H 0.0536 0.5237 0.1932 0.032 Uiso 1 1 calc R
C5 C 0.07783(16) 0.3942(2) 0.2517(4) 0.0217(7) Uani 1 1 d .
H5 H 0.0506 0.3646 0.1782 0.026 Uiso 1 1 calc R
C6 C 0.11669(14) 0.3453(2) 0.3529(3) 0.0134(5) Uani 1 1 d .
C7 C 0.11504(15) 0.2459(2) 0.3546(3) 0.0136(6) Uani 1 1 d .
C8 C 0.08365(15) 0.1911(2) 0.2504(3) 0.0165(6) Uani 1 1 d .
H8 H 0.0602 0.2167 0.1672 0.020 Uiso 1 1 calc R
C9 C 0.08660(15) 0.0981(2) 0.2680(3) 0.0192(6) Uani 1 1 d .
H9 H 0.0648 0.0599 0.1967 0.023 Uiso 1 1 calc R
C10 C 0.12122(14) 0.0602(2) 0.3892(3) 0.0179(6) Uani 1 1 d .
H10 H 0.1235 -0.0036 0.4002 0.021 Uiso 1 1 calc R
C11 C 0.15232(14) 0.1160(2) 0.4934(3) 0.0144(6) Uani 1 1 d .
C12 C 0.18907(15) 0.0825(2) 0.6296(3) 0.0188(6) Uani 1 1 d .
H12A H 0.2314 0.1041 0.6376 0.028 Uiso 1 1 calc R
H12B H 0.1887 0.0163 0.6303 0.028 Uiso 1 1 calc R
H12C H 0.1712 0.1053 0.7101 0.028 Uiso 1 1 calc R
C13 C 0.20492(16) 0.5166(2) 0.5791(4) 0.0231(7) Uani 1 1 d .
H13A H 0.2186 0.4717 0.6532 0.035 Uiso 1 1 calc R
H13B H 0.1862 0.5680 0.6208 0.035 Uiso 1 1 calc R
H13C H 0.2402 0.5378 0.5381 0.035 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'
Au Au -2.0133 8.8022 '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'
N N 0.0061 0.0033 '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
Cl2 Au1 Cl2 90.20(4) . 2_556
Cl2 Au1 Cl1 89.07(3) . .
Cl2 Au1 Cl1 178.30(3) 2_556 .
Cl2 Au1 Cl1 178.30(3) . 2_556
Cl2 Au1 Cl1 89.07(3) 2_556 2_556
Cl1 Au1 Cl1 91.70(4) . 2_556
Cl3 Au2 Cl3 180.0 7_557 .
Cl3 Au2 Cl4 90.29(3) 7_557 .
Cl3 Au2 Cl4 89.71(3) . .
Cl3 Au2 Cl4 89.71(3) 7_557 7_557
Cl3 Au2 Cl4 90.29(3) . 7_557
Cl4 Au2 Cl4 180.0 . 7_557
C2 N1 C6 118.0(3) . .
C11 N2 C7 124.5(3) . .
C11 N2 H2 119(3) . .
C7 N2 H2 117(3) . .
N1 C2 C3 122.1(3) . .
N1 C2 C13 117.3(3) . .
C3 C2 C13 120.6(3) . .
C4 C3 C2 119.1(3) . .
C4 C3 H3 120.5 . .
C2 C3 H3 120.5 . .
C3 C4 C5 119.4(3) . .
C3 C4 H4 120.3 . .
C5 C4 H4 120.3 . .
C6 C5 C4 118.1(3) . .
C6 C5 H5 121.0 . .
C4 C5 H5 121.0 . .
N1 C6 C5 123.3(3) . .
N1 C6 C7 115.5(3) . .
C5 C6 C7 121.2(3) . .
N2 C7 C8 118.2(3) . .
N2 C7 C6 115.6(3) . .
C8 C7 C6 126.2(3) . .
C7 C8 C9 119.3(3) . .
C7 C8 H8 120.3 . .
C9 C8 H8 120.3 . .
C8 C9 C10 120.6(3) . .
C8 C9 H9 119.7 . .
C10 C9 H9 119.7 . .
C11 C10 C9 119.6(3) . .
C11 C10 H10 120.2 . .
C9 C10 H10 120.2 . .
N2 C11 C10 117.9(3) . .
N2 C11 C12 118.1(3) . .
C10 C11 C12 123.9(3) . .
C11 C12 H12A 109.5 . .
C11 C12 H12B 109.5 . .
H12A C12 H12B 109.5 . .
C11 C12 H12C 109.5 . .
H12A C12 H12C 109.5 . .
H12B C12 H12C 109.5 . .
C2 C13 H13A 109.5 . .
C2 C13 H13B 109.5 . .
H13A C13 H13B 109.5 . .
C2 C13 H13C 109.5 . .
H13A C13 H13C 109.5 . .
H13B C13 H13C 109.5 . .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
Au1 Cl2 2.2779(7) .
Au1 Cl2 2.2780(7) 2_556
Au1 Cl1 2.2810(7) .
Au1 Cl1 2.2810(7) 2_556
Au2 Cl3 2.2833(8) 7_557
Au2 Cl3 2.2833(8) .
Au2 Cl4 2.2853(8) .
Au2 Cl4 2.2853(8) 7_557
N1 C2 1.343(4) .
N1 C6 1.346(4) .
N2 C11 1.347(4) .
N2 C7 1.364(4) .
N2 H2 0.82(4) .
C2 C3 1.395(4) .
C2 C13 1.502(4) .
C3 C4 1.376(5) .
C3 H3 0.9500 .
C4 C5 1.389(5) .
C4 H4 0.9500 .
C5 C6 1.383(4) .
C5 H5 0.9500 .
C6 C7 1.471(4) .
C7 C8 1.376(4) .
C8 C9 1.386(5) .
C8 H8 0.9500 .
C9 C10 1.392(4) .
C9 H9 0.9500 .
C10 C11 1.382(4) .
C10 H10 0.9500 .
C11 C12 1.494(4) .
C12 H12A 0.9800 .
C12 H12B 0.9800 .
C12 H12C 0.9800 .
C13 H13A 0.9800 .
C13 H13B 0.9800 .
C13 H13C 0.9800 .
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
N2 H2 Cl4 0.82(4) 2.79(4) 3.581(3) 160(4) 7_557
