# Electronic Supplementary Material (ESI) for Dalton Transactions.
# This journal is © The Royal Society of Chemistry 2014

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#                                CCDC 
# 
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# 
#  This CIF contains data from an original supplementary publication
#  deposited with the CCDC, and may include chemical, crystal,
#  experimental, refinement, atomic coordinates,
#  anisotropic displacement parameters and molecular geometry data,
#  as required by the journal to which it was submitted.
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#  fide research purposes only. It may contain copyright material
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data_niu3

_audit_update_record             
;
2014-11-03 # Formatted by publCIF

;
# publcif _publ_body_element loop end

_audit_creation_method           SHELXL-2013
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C12 H12 Au Cl N2'
_chemical_formula_weight         416.65

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'
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'

_space_group_crystal_system      orthorhombic
_space_group_IT_number           61
_space_group_name_H-M_alt        'P b c a'
_space_group_name_Hall           '-P 2ac 2ab'

_shelx_space_group_comment       
; 
The symmetry employed for this shelxl refinement is uniquely defined 
by the following loop, which should always be used as a source of 
symmetry information in preference to the above space-group names. 
They are only intended as comments. 
;

loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'-x, y+1/2, -z+1/2'
'x+1/2, -y+1/2, -z'
'-x, -y, -z'
'x-1/2, y, -z-1/2'
'x, -y-1/2, z-1/2'
'-x-1/2, y-1/2, z'

_cell_length_a                   16.1759(9)
_cell_length_b                   9.0017(5)
_cell_length_c                   17.1889(9)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     2502.9(2)
_cell_formula_units_Z            8
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    9344
_cell_measurement_theta_min      2.0
_cell_measurement_theta_max      28.0

_exptl_crystal_description       needles
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      .
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    2.211
_exptl_crystal_F_000             1552
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.281
_exptl_crystal_size_mid          0.052
_exptl_crystal_size_min          0.051
_exptl_absorpt_coefficient_mu    11.942
_shelx_estimated_absorpt_T_min   0.134
_shelx_estimated_absorpt_T_max   0.581
_exptl_absorpt_correction_type   analytical
_exptl_absorpt_correction_T_min  0.2865
_exptl_absorpt_correction_T_max  0.7333
_exptl_absorpt_process_details   
'based on measured indexed crystal faces, Bruker SHELXTL  v6.14 (Bruker 2008)'

_exptl_special_details           ?

_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'fine-focus sealed tube'
_diffrn_measurement_device_type  'Bruker APEX-II DUO'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            20748
_diffrn_reflns_av_unetI/netI     0.0196
_diffrn_reflns_av_R_equivalents  0.0385
_diffrn_reflns_limit_h_min       -21
_diffrn_reflns_limit_h_max       20
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_theta_min         2.370
_diffrn_reflns_theta_max         27.495
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measured_fraction_theta_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 1.000
_diffrn_reflns_point_group_measured_fraction_full 1.000
_reflns_number_total             2870
_reflns_number_gt                2349
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_reflns_special_details          
; 
 Reflections were merged by SHELXL according to the crystal 
 class for the calculation of statistics and refinement. 
  
 _reflns_Friedel_fraction is defined as the number of unique 
 Friedel pairs measured divided by the number that would be 
 possible theoretically, ignoring centric projections and 
 systematic absences. 
;

_computing_data_collection       'Bruker APEX2 (Bruker, 2008)'
_computing_cell_refinement       'Bruker APEX2'
_computing_data_reduction        'Bruker SAINT (Bruker, 2008)'
_computing_structure_solution    'SHELXL-2013 (Sheldrick, 2013)'
_computing_structure_refinement  'SHELXL-2013 (Sheldrick, 2013)'
_computing_molecular_graphics    'SHELXL-2013 (Sheldrick, 2013)'
_computing_publication_material  'SHELXL-2013 (Sheldrick, 2013)'

_refine_special_details          
; 
All H atoms were positioned geometrically ( C---H = 0.93/1.00 Å) and 
allowed to ride with Uiso(H)= 1.2/1.5Ueq(C). 
Methyl ones were allowed to rotate around the corresponding C---C. 

The proton, H11a, on C11 was obtained from a Difference Fourier map and refined
 freely.  
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0285P)²+13.9963P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         2870
_refine_ls_number_parameters     150
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0391
_refine_ls_R_factor_gt           0.0274
_refine_ls_wR_factor_ref         0.0719
_refine_ls_wR_factor_gt          0.0628
_refine_ls_goodness_of_fit_ref   1.091
_refine_ls_restrained_S_all      1.091
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

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_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Au1 Au 0.02022(2) 0.06422(2) 0.39029(2) 0.02737(8) Uani 1 1 d . . . . .
Cl1 Cl -0.11949(8) 0.08843(14) 0.37334(8) 0.0273(3) Uani 1 1 d . . . . .
N1 N 0.1913(3) 0.1253(5) 0.4477(2) 0.0276(10) Uani 1 1 d . . . . .
N2 N 0.1927(3) -0.0319(5) 0.3516(2) 0.0273(10) Uani 1 1 d . . . . .
C1 C 0.1413(4) 0.0487(6) 0.3984(3) 0.0313(13) Uani 1 1 d . . . . .
C2 C 0.2739(4) 0.0954(6) 0.4322(3) 0.0272(11) Uani 1 1 d . . . . .
C3 C 0.3468(4) 0.1478(7) 0.4652(3) 0.0346(13) Uani 1 1 d . . . . .
H3A H 0.3463 0.2174 0.5067 0.042 Uiso 1 1 calc R U . . .
C4 C 0.4192(4) 0.0944(7) 0.4351(4) 0.0406(15) Uani 1 1 d . . . . .
H4A H 0.4701 0.1291 0.4558 0.049 Uiso 1 1 calc R U . . .
C5 C 0.4206(4) -0.0101(8) 0.3744(4) 0.0418(15) Uani 1 1 d . . . . .
H5A H 0.4721 -0.0467 0.3561 0.050 Uiso 1 1 calc R U . . .
C6 C 0.3482(4) -0.0604(7) 0.3410(4) 0.0380(14) Uani 1 1 d . . . . .
H6A H 0.3487 -0.1295 0.2992 0.046 Uiso 1 1 calc R U . . .
C7 C 0.2750(4) -0.0058(6) 0.3710(3) 0.0274(11) Uani 1 1 d . . . . .
C8 C 0.1655(4) -0.1271(6) 0.2879(3) 0.0318(12) Uani 1 1 d . . . . .
H8A H 0.1055 -0.1459 0.2931 0.038 Uiso 1 1 calc R U . . .
H8B H 0.1944 -0.2239 0.2915 0.038 Uiso 1 1 calc R U . . .
C9 C 0.1827(4) -0.0579(6) 0.2079(3) 0.0345(13) Uani 1 1 d . . . . .
H9A H 0.2426 -0.0381 0.2029 0.041 Uiso 1 1 calc R U . . .
H9B H 0.1669 -0.1294 0.1668 0.041 Uiso 1 1 calc R U . . .
C10 C 0.1369(4) 0.0813(7) 0.1965(3) 0.0325(13) Uani 1 1 d . . . . .
C11 C 0.0989(5) 0.1913(8) 0.1874(3) 0.0404(15) Uani 1 1 d . . . . .
H11A H 0.070(4) 0.275(9) 0.171(4) 0.05(2) Uiso 1 1 d . . . . .
C12 C 0.1636(4) 0.2227(6) 0.5102(3) 0.0329(13) Uani 1 1 d . . . . .
H12A H 0.1033 0.2164 0.5149 0.049 Uiso 1 1 calc R U . . .
H12B H 0.1795 0.3252 0.4984 0.049 Uiso 1 1 calc R U . . .
H12C H 0.1893 0.1918 0.5592 0.049 Uiso 1 1 calc R U . . .


_geom_special_details            
; 
 All esds (except the esd in the dihedral angle between two l.s. planes) 
 are estimated using the full covariance matrix.  The cell esds are taken 
 into account individually in the estimation of esds in distances, angles 
 and torsion angles; correlations between esds in cell parameters are only 
 used when they are defined by crystal symmetry.  An approximate (isotropic) 
 treatment of cell esds is used for estimating esds involving l.s. planes. 
;

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Au1 C1 1.969(7) . ?
Au1 Cl1 2.2891(13) . ?
N1 C1 1.359(7) . ?
N1 C2 1.389(7) . ?
N1 C12 1.457(7) . ?
N2 C1 1.366(7) . ?
N2 C7 1.392(8) . ?
N2 C8 1.458(7) . ?
C2 C7 1.390(8) . ?
C2 C3 1.390(8) . ?
C3 C4 1.368(9) . ?
C3 H3A 0.9500 . ?
C4 C5 1.405(10) . ?
C4 H4A 0.9500 . ?
C5 C6 1.381(10) . ?
C5 H5A 0.9500 . ?
C6 C7 1.383(9) . ?
C6 H6A 0.9500 . ?
C8 C9 1.534(7) . ?
C8 H8A 0.9900 . ?
C8 H8B 0.9900 . ?
C9 C10 1.469(9) . ?
C9 H9A 0.9900 . ?
C9 H9B 0.9900 . ?
C10 C11 1.176(9) . ?
C11 H11A 0.93(8) . ?
C12 H12A 0.9800 . ?
C12 H12B 0.9800 . ?
C12 H12C 0.9800 . ?

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
_geom_angle_publ_flag
C1 Au1 Cl1 176.44(16) . . ?
C1 N1 C2 110.7(5) . . ?
C1 N1 C12 125.6(5) . . ?
C2 N1 C12 123.7(5) . . ?
C1 N2 C7 110.5(5) . . ?
C1 N2 C8 124.8(5) . . ?
C7 N2 C8 124.6(5) . . ?
N1 C1 N2 106.0(5) . . ?
N1 C1 Au1 126.8(4) . . ?
N2 C1 Au1 127.0(4) . . ?
N1 C2 C7 106.5(5) . . ?
N1 C2 C3 132.2(5) . . ?
C7 C2 C3 121.3(6) . . ?
C4 C3 C2 116.9(6) . . ?
C4 C3 H3A 121.5 . . ?
C2 C3 H3A 121.5 . . ?
C3 C4 C5 122.0(6) . . ?
C3 C4 H4A 119.0 . . ?
C5 C4 H4A 119.0 . . ?
C6 C5 C4 121.0(6) . . ?
C6 C5 H5A 119.5 . . ?
C4 C5 H5A 119.5 . . ?
C5 C6 C7 117.0(6) . . ?
C5 C6 H6A 121.5 . . ?
C7 C6 H6A 121.5 . . ?
C6 C7 C2 121.7(6) . . ?
C6 C7 N2 132.0(5) . . ?
C2 C7 N2 106.3(5) . . ?
N2 C8 C9 112.3(4) . . ?
N2 C8 H8A 109.2 . . ?
C9 C8 H8A 109.2 . . ?
N2 C8 H8B 109.2 . . ?
C9 C8 H8B 109.2 . . ?
H8A C8 H8B 107.9 . . ?
C10 C9 C8 112.1(5) . . ?
C10 C9 H9A 109.2 . . ?
C8 C9 H9A 109.2 . . ?
C10 C9 H9B 109.2 . . ?
C8 C9 H9B 109.2 . . ?
H9A C9 H9B 107.9 . . ?
C11 C10 C9 178.8(7) . . ?
C10 C11 H11A 170(5) . . ?
N1 C12 H12A 109.5 . . ?
N1 C12 H12B 109.5 . . ?
H12A C12 H12B 109.5 . . ?
N1 C12 H12C 109.5 . . ?
H12A C12 H12C 109.5 . . ?
H12B C12 H12C 109.5 . . ?

_refine_diff_density_max         1.692
_refine_diff_density_min         -0.827
_refine_diff_density_rms         0.154

_shelxl_version_number           2013-3


_exptl_crystal_recrystallization_method 'Re-crystallisation from solvent: '
_database_code_depnum_ccdc_archive 'CCDC 1033701'
