# Electronic Supplementary Material (ESI) for Dalton Transactions
# This journal is © The Royal Society of Chemistry 2013

#######################################################################
#
#                 Cambridge Crystallographic Data Centre
#                                CCDC 
# 
#######################################################################
# 
#  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.
#
#  This CIF is provided on the understanding that it is used for bona
#  fide research purposes only. It may contain copyright material
#  of the CCDC or of third parties, and may not be copied or further
#  disseminated in any form, whether machine-readable or not,
#  except for the purpose of generating routine backup copies
#  on your local computer system.
# 
#  For further information on the CCDC, data deposition and
#  data retrieval see:
#                         www.ccdc.cam.ac.uk
#
#  Bona fide researchers may freely download Mercury and enCIFer
#  from this site to visualise CIF-encoded structures and 
#  to carry out CIF format checking respectively.
#
data_I
_audit_creation_method           'APEX2 v2010.1-2'

_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C17 H16 Au Cl N4'
_chemical_formula_iupac          ?
_chemical_formula_weight         508.75
_chemical_absolute_configuration ?

_chemical_melting_point          ?

_space_group_crystal_system      orthorhombic
_space_group_name_H-M_alt        'P 21 21 21'
_space_group_name_Hall           'P 2ac 2ab'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'x+1/2, -y+1/2, -z'
'-x, y+1/2, -z+1/2'
'-x+1/2, -y, z+1/2'

_cell_length_a                   5.7600(8)
_cell_length_b                   7.9251(9)
_cell_length_c                   37.318(5)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     1703.5(4)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    2623
_cell_measurement_theta_min      3.27
_cell_measurement_theta_max      22.30
_cell_measurement_temperature    200.(2)

_exptl_crystal_description       platelet
_exptl_crystal_colour            orange
_exptl_crystal_size_max          0.73
_exptl_crystal_size_mid          0.42
_exptl_crystal_size_min          0.16
_exptl_crystal_density_diffrn    1.984
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             968

_exptl_absorpt_coefficient_mu    8.796
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS V2008/1 (Bruker AXS)'
_exptl_absorpt_correction_T_min  0.06
_exptl_absorpt_correction_T_max  0.33

_exptl_special_details           
;
;

_diffrn_ambient_temperature      200.(2)

_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_source         'sealed MicroFocus tube'
_diffrn_radiation_monochromator  'doubly curved silicon crystal'

_diffrn_measurement_device_type  'SMART X2S'
_diffrn_measurement_method       omega-scan

_diffrn_detector_area_resol_mean ?

_diffrn_reflns_number            16284
_diffrn_reflns_av_R_equivalents  0.1194
_diffrn_reflns_av_sigmaI/netI    0.0600
_diffrn_reflns_theta_min         2.79
_diffrn_reflns_theta_max         25.07
_diffrn_reflns_theta_full        25.07
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measured_fraction_theta_full 0.996
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_l_min       -44
_diffrn_reflns_limit_l_max       44

_refine_special_details          
;
Refinement of F^2^ against ALL reflections.  The weighted R-factor wR and
goodness of fit S are based on F^2^, conventional R-factors R are based
on F, with F set to zero for negative F^2^. The threshold expression of
F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is
not relevant to the choice of reflections for refinement.  R-factors based
on F^2^ are statistically about twice as large as those based on F, and R-
factors based on ALL data will be even larger.
;

_reflns_number_total             1801
_reflns_number_gt                1665
_reflns_threshold_expression     >2sigma(I)

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_R_factor_all          0.0572
_refine_ls_R_factor_gt           0.0512
_refine_ls_wR_factor_gt          0.1306
_refine_ls_wR_factor_ref         0.1335
_refine_ls_goodness_of_fit_ref   1.120
_refine_ls_restrained_S_all      1.120
_refine_ls_number_reflns         1801
_refine_ls_number_parameters     209
_refine_ls_number_restraints     0
_refine_ls_hydrogen_treatment    constr
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[\s^2^(Fo^2^)+(0.0734P)^2^+10.5934P] where P=(Fo^2^+2Fc^2^)/3'

_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap

_refine_ls_shift/su_max          0.009
_refine_ls_shift/su_mean         0.001
_refine_diff_density_max         1.890
_refine_diff_density_min         -2.673
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0.(10)

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 0.0000 '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 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cl Cl 0.1484 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Au Au -2.0133 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_computing_data_collection       'APEX2 Version 2009.9 (Bruker)'
_computing_cell_refinement       'SAINT Version 7.68A (Bruker, 2009)'
_computing_data_reduction        'SAINT (Bruker, 2009)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_molecular_graphics    
'ORTEP-3 for Windows version 2.02 (Farrugia, 1997)'
_computing_publication_material  'SHELXL-97 and publCIF (Westrip, 2010)'

loop_
_atom_site_type_symbol
_atom_site_label
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Au Au1 0.80012(13) 0.52657(8) 0.554127(18) 0.0308(2) Uani d . 1 . .
Cl Cl1 1.0331(7) 0.2921(5) 0.54746(11) 0.0292(9) Uani d . 1 . .
C C2 0.483(4) 0.999(3) 0.5524(5) 0.046(5) Uani d . 1 . .
H H2 0.4675 1.1112 0.5435 0.056 Uiso calc R 1 . .
N N3 0.658(3) 0.674(2) 0.7498(4) 0.040(4) Uani d . 1 . .
N N4 0.857(2) 0.622(2) 0.7547(4) 0.042(4) Uani d . 1 . .
C C1 0.617(3) 0.740(2) 0.5593(4) 0.027(4) Uani d . 1 . .
N N1 0.650(3) 0.883(2) 0.5422(4) 0.036(4) Uani d . 1 . .
C C3 0.352(4) 0.927(2) 0.5765(6) 0.044(5) Uani d . 1 . .
H H3 0.226 0.9794 0.5886 0.052 Uiso calc R 1 . .
N N2 0.427(3) 0.764(2) 0.5815(4) 0.039(4) Uani d . 1 . .
C C4 0.327(3) 0.640(3) 0.6051(4) 0.042(5) Uani d . 1 . .
H H4A 0.3576 0.5266 0.5952 0.05 Uiso calc R 1 . .
H H4B 0.1565 0.6566 0.6055 0.05 Uiso calc R 1 . .
C C5 0.416(3) 0.646(2) 0.6429(5) 0.032(4) Uani d . 1 . .
C C10 0.294(4) 0.728(2) 0.6699(4) 0.035(4) Uani d . 1 . .
H H10 0.1503 0.7813 0.6646 0.042 Uiso calc R 1 . .
C C9 0.378(3) 0.732(3) 0.7034(6) 0.042(5) Uani d . 1 . .
H H9 0.2926 0.7889 0.7214 0.05 Uiso calc R 1 . .
C C8 0.587(3) 0.655(2) 0.7125(5) 0.034(4) Uani d . 1 . .
C C11 0.930(3) 0.637(3) 0.7915(5) 0.037(5) Uani d . 1 . .
C C12 0.811(4) 0.717(2) 0.8183(5) 0.038(4) Uani d . 1 . .
H H12 0.6672 0.771 0.813 0.045 Uiso calc R 1 . .
C C13 0.896(4) 0.722(3) 0.8527(5) 0.047(5) Uani d . 1 . .
H H13 0.8131 0.7777 0.8713 0.056 Uiso calc R 1 . .
C C14 1.109(4) 0.641(3) 0.8596(5) 0.042(5) Uani d . 1 . .
H H14 1.1732 0.6438 0.883 0.051 Uiso calc R 1 . .
C C15 1.221(4) 0.561(3) 0.8330(5) 0.045(5) Uani d . 1 . .
H H15 1.3587 0.5002 0.8384 0.054 Uiso calc R 1 . .
C C16 1.142(3) 0.564(3) 0.7993(6) 0.043(5) Uani d . 1 . .
H H16 1.2329 0.5157 0.7806 0.052 Uiso calc R 1 . .
C C7 0.710(3) 0.575(3) 0.6858(5) 0.047(5) Uani d . 1 . .
H H7 0.855 0.5239 0.6913 0.056 Uiso calc R 1 . .
C C6 0.627(3) 0.567(2) 0.6521(5) 0.038(5) Uani d . 1 . .
H H6 0.7112 0.5075 0.6343 0.045 Uiso calc R 1 . .
C C17 0.825(3) 0.904(2) 0.5141(5) 0.041(4) Uani d . 1 . .
H H17A 0.9737 0.936 0.5251 0.061 Uiso calc R 1 . .
H H17B 0.7756 0.9928 0.4975 0.061 Uiso calc R 1 . .
H H17C 0.844 0.7978 0.501 0.061 Uiso calc R 1 . .

loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_12
_atom_site_aniso_U_13
_atom_site_aniso_U_23
Au1 0.0319(4) 0.0235(4) 0.0369(4) 0.0038(3) -0.0030(3) -0.0006(3)
Cl1 0.034(2) 0.018(2) 0.036(2) 0.0115(16) 0.0014(18) 0.0024(17)
C2 0.051(11) 0.039(12) 0.049(11) 0.005(9) -0.018(10) -0.015(11)
N3 0.026(9) 0.040(9) 0.054(10) -0.005(7) 0.001(7) 0.008(8)
N4 0.021(8) 0.059(12) 0.045(9) 0.010(7) -0.003(6) -0.001(8)
C1 0.028(8) 0.032(10) 0.021(8) 0.004(7) -0.004(7) 0.000(8)
N1 0.035(9) 0.032(9) 0.041(8) 0.005(7) -0.003(6) -0.005(7)
C3 0.051(13) 0.031(11) 0.049(11) 0.010(9) -0.001(10) 0.007(9)
N2 0.029(8) 0.039(10) 0.048(9) 0.004(8) -0.007(7) -0.009(8)
C4 0.027(10) 0.064(14) 0.035(10) -0.008(10) -0.004(8) 0.000(9)
C5 0.014(8) 0.033(10) 0.049(11) -0.008(8) 0.004(8) 0.009(9)
C10 0.030(8) 0.040(10) 0.037(10) 0.003(10) 0.005(9) 0.002(8)
C9 0.033(9) 0.036(11) 0.056(12) 0.004(9) 0.014(9) -0.008(10)
C8 0.028(9) 0.036(10) 0.037(10) -0.008(9) 0.003(8) 0.001(8)
C11 0.024(9) 0.046(12) 0.041(10) -0.014(9) -0.005(8) -0.002(9)
C12 0.026(8) 0.045(11) 0.042(10) 0.000(11) 0.004(10) -0.008(9)
C13 0.039(10) 0.052(14) 0.050(12) -0.002(11) 0.016(10) -0.002(10)
C14 0.049(12) 0.039(11) 0.039(10) -0.008(10) -0.012(9) 0.017(9)
C15 0.054(12) 0.044(12) 0.038(10) -0.003(11) 0.000(9) 0.003(9)
C16 0.018(8) 0.053(13) 0.060(12) -0.003(8) 0.009(8) -0.007(11)
C7 0.022(8) 0.064(14) 0.054(11) -0.002(11) -0.016(9) 0.013(11)
C6 0.029(9) 0.027(11) 0.057(12) 0.000(8) 0.009(8) 0.006(9)
C17 0.032(10) 0.024(9) 0.067(12) 0.011(9) 0.009(10) 0.006(9)

_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_site_symmetry_2
_geom_bond_distance
_geom_bond_publ_flag
Au1 C1 . 2.004(17) ?
Au1 Cl1 . 2.306(4) ?
C2 C3 . 1.31(3) ?
C2 N1 . 1.38(2) ?
C2 H2 . 0.95 ?
N3 N4 . 1.24(2) ?
N3 C8 . 1.46(2) ?
N4 C11 . 1.44(2) ?
C1 N1 . 1.31(2) ?
C1 N2 . 1.39(2) ?
N1 C17 . 1.47(2) ?
C3 N2 . 1.38(2) ?
C3 H3 . 0.95 ?
N2 C4 . 1.43(2) ?
C4 C5 . 1.50(2) ?
C4 H4A . 0.99 ?
C4 H4B . 0.99 ?
C5 C10 . 1.39(2) ?
C5 C6 . 1.41(2) ?
C10 C9 . 1.34(3) ?
C10 H10 . 0.95 ?
C9 C8 . 1.39(3) ?
C9 H9 . 0.95 ?
C8 C7 . 1.37(3) ?
C11 C12 . 1.37(3) ?
C11 C16 . 1.39(3) ?
C12 C13 . 1.38(3) ?
C12 H12 . 0.95 ?
C13 C14 . 1.41(3) ?
C13 H13 . 0.95 ?
C14 C15 . 1.34(3) ?
C14 H14 . 0.95 ?
C15 C16 . 1.34(3) ?
C15 H15 . 0.95 ?
C16 H16 . 0.95 ?
C7 C6 . 1.35(3) ?
C7 H7 . 0.95 ?
C6 H6 . 0.95 ?
C17 H17A . 0.98 ?
C17 H17B . 0.98 ?
C17 H17C . 0.98 ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle
_geom_angle_publ_flag
C1 Au1 Cl1 . . 176.0(5) ?
C3 C2 N1 . . 107.3(19) ?
C3 C2 H2 . . 126.4 ?
N1 C2 H2 . . 126.4 ?
N4 N3 C8 . . 111.6(17) ?
N3 N4 C11 . . 112.6(16) ?
N1 C1 N2 . . 106.8(15) ?
N1 C1 Au1 . . 127.3(13) ?
N2 C1 Au1 . . 125.9(13) ?
C1 N1 C2 . . 110.1(16) ?
C1 N1 C17 . . 123.1(15) ?
C2 N1 C17 . . 126.6(17) ?
C2 C3 N2 . . 108.9(19) ?
C2 C3 H3 . . 125.6 ?
N2 C3 H3 . . 125.6 ?
C1 N2 C3 . . 106.9(17) ?
C1 N2 C4 . . 126.4(17) ?
C3 N2 C4 . . 126.7(18) ?
N2 C4 C5 . . 114.7(16) ?
N2 C4 H4A . . 108.6 ?
C5 C4 H4A . . 108.6 ?
N2 C4 H4B . . 108.6 ?
C5 C4 H4B . . 108.6 ?
H4A C4 H4B . . 107.6 ?
C10 C5 C6 . . 117.8(18) ?
C10 C5 C4 . . 121.7(17) ?
C6 C5 C4 . . 120.6(18) ?
C9 C10 C5 . . 120.3(19) ?
C9 C10 H10 . . 119.9 ?
C5 C10 H10 . . 119.9 ?
C10 C9 C8 . . 122.0(19) ?
C10 C9 H9 . . 119.0 ?
C8 C9 H9 . . 119.0 ?
C7 C8 C9 . . 118.1(18) ?
C7 C8 N3 . . 126.5(18) ?
C9 C8 N3 . . 115.4(17) ?
C12 C11 C16 . . 119.0(19) ?
C12 C11 N4 . . 126.1(18) ?
C16 C11 N4 . . 114.9(18) ?
C11 C12 C13 . . 121.(2) ?
C11 C12 H12 . . 119.5 ?
C13 C12 H12 . . 119.5 ?
C12 C13 C14 . . 117.9(19) ?
C12 C13 H13 . . 121.0 ?
C14 C13 H13 . . 121.0 ?
C15 C14 C13 . . 120.0(19) ?
C15 C14 H14 . . 120.0 ?
C13 C14 H14 . . 120.0 ?
C16 C15 C14 . . 122.(2) ?
C16 C15 H15 . . 119.2 ?
C14 C15 H15 . . 119.2 ?
C15 C16 C11 . . 120.1(19) ?
C15 C16 H16 . . 119.9 ?
C11 C16 H16 . . 119.9 ?
C6 C7 C8 . . 120.8(19) ?
C6 C7 H7 . . 119.6 ?
C8 C7 H7 . . 119.6 ?
C7 C6 C5 . . 121.0(19) ?
C7 C6 H6 . . 119.5 ?
C5 C6 H6 . . 119.5 ?
N1 C17 H17A . . 109.5 ?
N1 C17 H17B . . 109.5 ?
H17A C17 H17B . . 109.5 ?
N1 C17 H17C . . 109.5 ?
H17A C17 H17C . . 109.5 ?
H17B C17 H17C . . 109.5 ?

_database_code_depnum_ccdc_archive 'CCDC 944152'
#######################################################################
#
#                 Cambridge Crystallographic Data Centre
#                                CCDC 
# 
#######################################################################
# 
#  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.
#
#  This CIF is provided on the understanding that it is used for bona
#  fide research purposes only. It may contain copyright material
#  of the CCDC or of third parties, and may not be copied or further
#  disseminated in any form, whether machine-readable or not,
#  except for the purpose of generating routine backup copies
#  on your local computer system.
# 
#  For further information on the CCDC, data deposition and
#  data retrieval see:
#                         www.ccdc.cam.ac.uk
#
#  Bona fide researchers may freely download Mercury and enCIFer
#  from this site to visualise CIF-encoded structures and 
#  to carry out CIF format checking respectively.
#
data_I
_audit_creation_method           'APEX2 v2010.1-2'

_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C22 H19 Br N4'
_chemical_formula_iupac          ?
_chemical_formula_weight         419.32

_chemical_melting_point          ?

_space_group_crystal_system      monoclinic
_space_group_name_H-M_alt        'P 1 21/n 1'
_space_group_name_Hall           '-P 2yn'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, -y-1/2, z-1/2'

_cell_length_a                   14.5077(15)
_cell_length_b                   9.0862(8)
_cell_length_c                   15.0053(15)
_cell_angle_alpha                90
_cell_angle_beta                 90.935(4)
_cell_angle_gamma                90
_cell_volume                     1977.7(3)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    4434
_cell_measurement_theta_min      2.28
_cell_measurement_theta_max      22.22
_cell_measurement_temperature    200.(2)

_exptl_crystal_description       prism
_exptl_crystal_colour            orange
_exptl_crystal_size_max          0.46
_exptl_crystal_size_mid          0.37
_exptl_crystal_size_min          0.24
_exptl_crystal_density_diffrn    1.408
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             856

_exptl_absorpt_coefficient_mu    2.092
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS V2008/1 (Bruker AXS)'
_exptl_absorpt_correction_T_min  0.45
_exptl_absorpt_correction_T_max  0.63

_exptl_special_details           
;
;

_diffrn_ambient_temperature      200.(2)

_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_source         'sealed MicroFocus tube'
_diffrn_radiation_monochromator  'doubly curved silicon crystal'

_diffrn_measurement_device_type  'SMART X2S'
_diffrn_measurement_method       omega-scan

_diffrn_detector_area_resol_mean ?

_diffrn_reflns_number            21594
_diffrn_reflns_av_R_equivalents  0.0521
_diffrn_reflns_av_sigmaI/netI    0.0317
_diffrn_reflns_theta_min         2.62
_diffrn_reflns_theta_max         25.03
_diffrn_reflns_theta_full        25.03
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measured_fraction_theta_full 0.998
_diffrn_reflns_limit_h_min       -17
_diffrn_reflns_limit_h_max       17
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_limit_l_max       17

_refine_special_details          
;
Refinement of F^2^ against ALL reflections.  The weighted R-factor wR and
goodness of fit S are based on F^2^, conventional R-factors R are based
on F, with F set to zero for negative F^2^. The threshold expression of
F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is
not relevant to the choice of reflections for refinement.  R-factors based
on F^2^ are statistically about twice as large as those based on F, and R-
factors based on ALL data will be even larger.
;

_reflns_number_total             3488
_reflns_number_gt                2776
_reflns_threshold_expression     >2sigma(I)

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_R_factor_all          0.0459
_refine_ls_R_factor_gt           0.0321
_refine_ls_wR_factor_gt          0.0720
_refine_ls_wR_factor_ref         0.0789
_refine_ls_goodness_of_fit_ref   1.040
_refine_ls_restrained_S_all      1.040
_refine_ls_number_reflns         3488
_refine_ls_number_parameters     244
_refine_ls_number_restraints     0
_refine_ls_hydrogen_treatment    constr
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[\s^2^(Fo^2^)+(0.0312P)^2^+0.9305P] where P=(Fo^2^+2Fc^2^)/3'

_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap

_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_diff_density_max         0.407
_refine_diff_density_min         -0.235
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?

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'
Br Br -0.2901 2.4595 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_computing_data_collection       'APEX2 Version 2009.9 (Bruker)'
_computing_cell_refinement       'SAINT Version 7.68A (Bruker, 2009)'
_computing_data_reduction        'SAINT (Bruker, 2009)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_molecular_graphics    
'ORTEP-3 for Windows version 2.02 (Farrugia, 1997)'
_computing_publication_material  'SHELXL-97 and publCIF (Westrip, 2010)'

loop_
_atom_site_type_symbol
_atom_site_label
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Br Br1 0.39695(2) 0.19632(3) 0.074923(17) 0.05251(11) Uani d . 1 . .
N N4 0.57039(17) 0.7756(3) 0.43860(15) 0.0583(6) Uani d . 1 . .
N N3 0.55367(16) 0.6610(2) 0.39750(15) 0.0549(6) Uani d . 1 . .
N N2 0.39774(14) 0.7056(2) 0.05450(13) 0.0414(5) Uani d . 1 . .
N N1 0.35155(18) 0.7992(2) -0.07003(14) 0.0543(6) Uani d . 1 . .
C C13 0.7014(2) 0.7410(5) 0.6885(2) 0.0791(10) Uani d . 1 . .
H H1 0.7295 0.7354 0.746 0.095 Uiso calc R 1 . .
C C14 0.6698(2) 0.8726(5) 0.6565(2) 0.0874(12) Uani d . 1 . .
H H2 0.6766 0.9588 0.6918 0.105 Uiso calc R 1 . .
C C15 0.6280(2) 0.8817(4) 0.5735(2) 0.0795(10) Uani d . 1 . .
H H3 0.6071 0.974 0.5513 0.095 Uiso calc R 1 . .
C C10 0.61658(19) 0.7557(3) 0.52249(18) 0.0544(7) Uani d . 1 . .
C C7 0.51035(17) 0.6811(3) 0.31277(17) 0.0456(6) Uani d . 1 . .
C C8 0.4884(2) 0.8162(3) 0.27564(18) 0.0545(7) Uani d . 1 . .
H H6 0.4994 0.9038 0.3087 0.065 Uiso calc R 1 . .
C C9 0.4508(2) 0.8244(3) 0.19128(18) 0.0558(7) Uani d . 1 . .
H H7 0.4354 0.9173 0.1661 0.067 Uiso calc R 1 . .
C C4 0.43532(17) 0.6958(2) 0.14262(16) 0.0403(5) Uani d . 1 . .
C C1 0.3874(2) 0.8298(3) 0.00803(17) 0.0516(7) Uani d . 1 . .
H H9 0.4037 0.9254 0.0285 0.062 Uiso calc R 1 . .
C C16 0.3275(3) 0.9139(3) -0.1367(2) 0.0929(13) Uani d . 1 . .
H H10A 0.3741 0.9935 -0.1331 0.111 Uiso calc R 1 . .
H H10B 0.2671 0.957 -0.1217 0.111 Uiso calc R 1 . .
C C17 0.3229(2) 0.8574(3) -0.23021(17) 0.0475(6) Uani d . 1 . .
C C18 0.3995(2) 0.8210(3) -0.2760(2) 0.0612(8) Uani d . 1 . .
H H12 0.4589 0.8275 -0.2487 0.073 Uiso calc R 1 . .
C C19 0.3893(3) 0.7735(3) -0.3647(3) 0.0813(11) Uani d . 1 . .
H H13 0.4419 0.7477 -0.3983 0.098 Uiso calc R 1 . .
C C20 0.3023(3) 0.7647(3) -0.4027(2) 0.0756(11) Uani d . 1 . .
H H14 0.2952 0.7327 -0.4627 0.091 Uiso calc R 1 . .
C C6 0.4927(2) 0.5548(3) 0.26412(18) 0.0582(7) Uani d . 1 . .
H H15 0.5063 0.4616 0.2899 0.07 Uiso calc R 1 . .
C C5 0.45588(19) 0.5612(3) 0.17911(17) 0.0526(7) Uani d . 1 . .
H H16 0.4448 0.4736 0.1461 0.063 Uiso calc R 1 . .
C C21 0.2290(3) 0.8000(3) -0.3568(3) 0.0760(10) Uani d . 1 . .
H H17 0.1694 0.7931 -0.3837 0.091 Uiso calc R 1 . .
C C22 0.2383(2) 0.8459(3) -0.2717(2) 0.0636(8) Uani d . 1 . .
H H22 0.1847 0.8711 -0.2396 0.076 Uiso calc R 1 . .
C C2 0.3382(2) 0.6502(3) -0.07615(18) 0.0591(8) Uani d . 1 . .
H H19 0.3132 0.5985 -0.126 0.071 Uiso calc R 1 . .
C C3 0.36685(19) 0.5911(3) 0.00078(17) 0.0516(7) Uani d . 1 . .
H H20 0.3662 0.4896 0.0159 0.062 Uiso calc R 1 . .
C C11 0.6492(2) 0.6230(4) 0.5544(2) 0.0669(8) Uani d . 1 . .
H H21 0.6421 0.5362 0.5197 0.08 Uiso calc R 1 . .
C C12 0.6921(2) 0.6167(5) 0.6370(2) 0.0823(10) Uani d . 1 . .
H H12A 0.7156 0.5256 0.6585 0.099 Uiso calc R 1 . .

loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_12
_atom_site_aniso_U_13
_atom_site_aniso_U_23
Br1 0.0794(2) 0.03161(15) 0.04595(17) 0.00360(12) -0.01722(13) -0.00522(11)
N4 0.0709(15) 0.0585(15) 0.0451(13) 0.0050(12) -0.0070(11) -0.0108(11)
N3 0.0672(15) 0.0508(13) 0.0462(13) 0.0028(11) -0.0104(11) -0.0060(10)
N2 0.0578(12) 0.0322(11) 0.0344(11) 0.0044(9) 0.0015(9) -0.0046(8)
N1 0.0921(17) 0.0341(11) 0.0364(12) 0.0117(11) -0.0065(11) -0.0032(9)
C13 0.0571(19) 0.130(3) 0.0500(19) 0.006(2) -0.0094(15) -0.015(2)
C14 0.081(2) 0.113(3) 0.067(2) 0.015(2) -0.0219(18) -0.040(2)
C15 0.090(2) 0.082(2) 0.066(2) 0.0156(19) -0.0217(18) -0.0265(18)
C10 0.0526(16) 0.0706(18) 0.0401(15) 0.0022(14) 0.0001(12) -0.0090(13)
C7 0.0504(14) 0.0452(15) 0.0411(14) 0.0019(11) -0.0028(11) -0.0029(11)
C8 0.0779(19) 0.0404(15) 0.0449(15) 0.0044(13) -0.0086(13) -0.0117(12)
C9 0.086(2) 0.0346(14) 0.0467(16) 0.0075(13) -0.0108(14) -0.0032(11)
C4 0.0481(13) 0.0367(13) 0.0363(13) 0.0021(11) 0.0024(10) -0.0031(10)
C1 0.0832(19) 0.0310(14) 0.0403(15) 0.0075(12) -0.0034(13) -0.0062(11)
C16 0.186(4) 0.0443(17) 0.0474(18) 0.032(2) -0.020(2) 0.0006(14)
C17 0.0742(19) 0.0298(12) 0.0383(14) 0.0060(12) -0.0085(13) 0.0027(10)
C18 0.0537(17) 0.0462(16) 0.083(2) 0.0004(13) -0.0124(16) 0.0031(15)
C19 0.104(3) 0.052(2) 0.089(3) 0.0147(18) 0.045(2) 0.0051(18)
C20 0.140(4) 0.0408(17) 0.0453(18) 0.003(2) -0.025(2) 0.0043(13)
C6 0.085(2) 0.0369(14) 0.0518(17) 0.0044(13) -0.0191(15) 0.0024(12)
C5 0.0747(19) 0.0328(14) 0.0499(16) 0.0008(12) -0.0107(14) -0.0062(11)
C21 0.095(3) 0.0466(18) 0.085(3) -0.0080(18) -0.043(2) 0.0103(17)
C22 0.0578(18) 0.0561(17) 0.077(2) 0.0033(14) 0.0007(16) 0.0173(15)
C2 0.096(2) 0.0366(14) 0.0440(16) 0.0013(14) -0.0146(15) -0.0063(12)
C3 0.0810(19) 0.0311(13) 0.0424(15) -0.0027(13) -0.0092(13) -0.0044(11)
C11 0.078(2) 0.073(2) 0.0493(18) 0.0019(17) -0.0092(15) -0.0043(15)
C12 0.087(2) 0.100(3) 0.059(2) 0.007(2) -0.0201(18) 0.0058(19)

_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_site_symmetry_2
_geom_bond_distance
_geom_bond_publ_flag
N4 N3 . 1.232(3) ?
N4 C10 . 1.428(3) ?
N3 C7 . 1.421(3) ?
N2 C1 . 1.334(3) ?
N2 C3 . 1.386(3) ?
N2 C4 . 1.425(3) ?
N1 C1 . 1.304(3) ?
N1 C2 . 1.371(3) ?
N1 C16 . 1.483(3) ?
C13 C14 . 1.365(5) ?
C13 C12 . 1.373(5) ?
C13 H1 . 0.95 ?
C14 C15 . 1.379(4) ?
C14 H2 . 0.95 ?
C15 C10 . 1.385(4) ?
C15 H3 . 0.95 ?
C10 C11 . 1.379(4) ?
C7 C6 . 1.382(4) ?
C7 C8 . 1.383(3) ?
C8 C9 . 1.372(4) ?
C8 H6 . 0.95 ?
C9 C4 . 1.394(3) ?
C9 H7 . 0.95 ?
C4 C5 . 1.371(3) ?
C1 H9 . 0.95 ?
C16 C17 . 1.494(4) ?
C16 H10A . 0.99 ?
C16 H10B . 0.99 ?
C17 C18 . 1.358(4) ?
C17 C22 . 1.371(4) ?
C18 C19 . 1.404(5) ?
C18 H12 . 0.95 ?
C19 C20 . 1.378(5) ?
C19 H13 . 0.95 ?
C20 C21 . 1.317(5) ?
C20 H14 . 0.95 ?
C6 C5 . 1.376(3) ?
C6 H15 . 0.95 ?
C5 H16 . 0.95 ?
C21 C22 . 1.347(5) ?
C21 H17 . 0.95 ?
C22 H22 . 0.95 ?
C2 C3 . 1.333(4) ?
C2 H19 . 0.95 ?
C3 H20 . 0.95 ?
C11 C12 . 1.379(4) ?
C11 H21 . 0.95 ?
C12 H12A . 0.95 ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle
_geom_angle_publ_flag
N3 N4 C10 . . 114.9(2) ?
N4 N3 C7 . . 114.9(2) ?
C1 N2 C3 . . 107.4(2) ?
C1 N2 C4 . . 125.2(2) ?
C3 N2 C4 . . 127.46(19) ?
C1 N1 C2 . . 108.9(2) ?
C1 N1 C16 . . 122.9(2) ?
C2 N1 C16 . . 128.2(2) ?
C14 C13 C12 . . 119.5(3) ?
C14 C13 H1 . . 120.2 ?
C12 C13 H1 . . 120.2 ?
C13 C14 C15 . . 120.7(3) ?
C13 C14 H2 . . 119.6 ?
C15 C14 H2 . . 119.6 ?
C14 C15 C10 . . 119.7(3) ?
C14 C15 H3 . . 120.1 ?
C10 C15 H3 . . 120.1 ?
C11 C10 C15 . . 119.6(3) ?
C11 C10 N4 . . 124.8(3) ?
C15 C10 N4 . . 115.6(3) ?
C6 C7 C8 . . 119.0(2) ?
C6 C7 N3 . . 116.2(2) ?
C8 C7 N3 . . 124.7(2) ?
C9 C8 C7 . . 120.3(2) ?
C9 C8 H6 . . 119.8 ?
C7 C8 H6 . . 119.8 ?
C8 C9 C4 . . 119.7(2) ?
C8 C9 H7 . . 120.1 ?
C4 C9 H7 . . 120.1 ?
C5 C4 C9 . . 120.4(2) ?
C5 C4 N2 . . 120.3(2) ?
C9 C4 N2 . . 119.3(2) ?
N1 C1 N2 . . 109.2(2) ?
N1 C1 H9 . . 125.4 ?
N2 C1 H9 . . 125.4 ?
N1 C16 C17 . . 113.5(2) ?
N1 C16 H10A . . 108.9 ?
C17 C16 H10A . . 108.9 ?
N1 C16 H10B . . 108.9 ?
C17 C16 H10B . . 108.9 ?
H10A C16 H10B . . 107.7 ?
C18 C17 C22 . . 119.0(3) ?
C18 C17 C16 . . 122.3(3) ?
C22 C17 C16 . . 118.6(3) ?
C17 C18 C19 . . 118.7(3) ?
C17 C18 H12 . . 120.7 ?
C19 C18 H12 . . 120.7 ?
C20 C19 C18 . . 119.4(3) ?
C20 C19 H13 . . 120.3 ?
C18 C19 H13 . . 120.3 ?
C21 C20 C19 . . 120.8(3) ?
C21 C20 H14 . . 119.6 ?
C19 C20 H14 . . 119.6 ?
C5 C6 C7 . . 121.3(2) ?
C5 C6 H15 . . 119.3 ?
C7 C6 H15 . . 119.3 ?
C4 C5 C6 . . 119.1(2) ?
C4 C5 H16 . . 120.4 ?
C6 C5 H16 . . 120.4 ?
C20 C21 C22 . . 120.1(3) ?
C20 C21 H17 . . 119.9 ?
C22 C21 H17 . . 119.9 ?
C21 C22 C17 . . 122.0(3) ?
C21 C22 H22 . . 119.0 ?
C17 C22 H22 . . 119.0 ?
C3 C2 N1 . . 107.3(2) ?
C3 C2 H19 . . 126.3 ?
N1 C2 H19 . . 126.3 ?
C2 C3 N2 . . 107.1(2) ?
C2 C3 H20 . . 126.4 ?
N2 C3 H20 . . 126.4 ?
C10 C11 C12 . . 119.7(3) ?
C10 C11 H21 . . 120.1 ?
C12 C11 H21 . . 120.1 ?
C13 C12 C11 . . 120.7(3) ?
C13 C12 H12A . . 119.7 ?
C11 C12 H12A . . 119.7 ?

_database_code_depnum_ccdc_archive 'CCDC 944153'
#######################################################################
#
#                 Cambridge Crystallographic Data Centre
#                                CCDC 
# 
#######################################################################
# 
#  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.
#
#  This CIF is provided on the understanding that it is used for bona
#  fide research purposes only. It may contain copyright material
#  of the CCDC or of third parties, and may not be copied or further
#  disseminated in any form, whether machine-readable or not,
#  except for the purpose of generating routine backup copies
#  on your local computer system.
# 
#  For further information on the CCDC, data deposition and
#  data retrieval see:
#                         www.ccdc.cam.ac.uk
#
#  Bona fide researchers may freely download Mercury and enCIFer
#  from this site to visualise CIF-encoded structures and 
#  to carry out CIF format checking respectively.
#
data_I
_vrf_REFNR01_I                   
;
PROBLEM: Ratio of reflections to parameters is < 6 for a
RESPONSE: All crystals were of low quality and weakly diffracting.
Therefore, no signals could be detected at high theta-angles.
;
_vrf_THETM01_I                   
;
PROBLEM: The value of sine(theta_max)/wavelength is less than 0.550
RESPONSE: see above
;
_vrf_PLAT023_I                   
;
PROBLEM: Resolution (too) Low [sin(theta)/Lambda < 0.6]..      19.18 Deg. 
RESPONSE: see above
;

_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_formula_moiety         'C22 H19 N4, F6 P'
_chemical_formula_sum            'C22 H19 F6 N4 P'
_chemical_formula_iupac          ?
_chemical_formula_weight         484.38

_chemical_melting_point          ?

_space_group_crystal_system      monoclinic
_space_group_name_H-M_alt        'C 1 2/c 1'
_space_group_name_Hall           '-C 2yc'
loop_
_space_group_symop_operation_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'

_cell_length_a                   25.965(5)
_cell_length_b                   12.038(2)
_cell_length_c                   14.377(3)
_cell_angle_alpha                90
_cell_angle_beta                 105.212(7)
_cell_angle_gamma                90
_cell_volume                     4336.3(15)
_cell_formula_units_Z            8
_cell_measurement_reflns_used    5529
_cell_measurement_theta_min      2.24
_cell_measurement_theta_max      19.07
_cell_measurement_temperature    205.(2)

_exptl_crystal_description       prism
_exptl_crystal_colour            orange
_exptl_crystal_size_max          0.370
_exptl_crystal_size_mid          0.280
_exptl_crystal_size_min          0.160
_exptl_crystal_density_diffrn    1.484
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1984

_exptl_absorpt_coefficient_mu    0.196
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS V2008/1 (Bruker AXS)'
_exptl_absorpt_correction_T_min  0.93
_exptl_absorpt_correction_T_max  0.97

_exptl_special_details           
;
;

_diffrn_ambient_temperature      205.(2)

_diffrn_source                   ?
_diffrn_source_type              ?

_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_source         'sealed MicroFocus tube'
_diffrn_radiation_monochromator  'doubly curved silicon crystal'

_diffrn_measurement_device_type  'SMART X2S'
_diffrn_measurement_method       omega-scan

_diffrn_detector_area_resol_mean ?

_diffrn_reflns_number            22246
_diffrn_reflns_av_R_equivalents  0.1037
_diffrn_reflns_av_sigmaI/netI    0.0580
_diffrn_reflns_theta_min         2.51
_diffrn_reflns_theta_max         19.18
_diffrn_reflns_theta_full        19.18
_diffrn_measured_fraction_theta_max 0.989
_diffrn_measured_fraction_theta_full 0.989
_diffrn_reflns_limit_h_min       -23
_diffrn_reflns_limit_h_max       23
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_limit_l_max       13

_refine_special_details          
;
Refinement of F^2^ against ALL reflections.  The weighted R-factor wR and
goodness of fit S are based on F^2^, conventional R-factors R are based
on F, with F set to zero for negative F^2^. The threshold expression of
F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is
not relevant to the choice of reflections for refinement.  R-factors based
on F^2^ are statistically about twice as large as those based on F, and R-
factors based on ALL data will be even larger.
;

_reflns_number_total             1781
_reflns_number_gt                1519
_reflns_threshold_expression     >2sigma(I)

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_R_factor_all          0.0620
_refine_ls_R_factor_gt           0.0534
_refine_ls_wR_factor_gt          0.1380
_refine_ls_wR_factor_ref         0.1442
_refine_ls_goodness_of_fit_ref   1.079
_refine_ls_restrained_S_all      1.079
_refine_ls_number_reflns         1781
_refine_ls_number_parameters     298
_refine_ls_number_restraints     0
_refine_ls_hydrogen_treatment    constr
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[\s^2^(Fo^2^)+(0.0545P)^2^+15.1905P] where P=(Fo^2^+2Fc^2^)/3'

_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap

_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_diff_density_max         0.467
_refine_diff_density_min         -0.340
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?

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'
P P 0.1023 0.0942 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'


_computing_data_collection       'APEX2 Version 2009.9 (Bruker)'
_computing_cell_refinement       'SAINT V8.27B (Bruker AXS Inc., 2012)'
_computing_data_reduction        'SAINT V8.27B (Bruker AXS Inc., 2012)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_molecular_graphics    
'ORTEP-3 for Windows version 2.02 (Farrugia, 1997)'
_computing_publication_material  'SHELXL-97 and publCIF'

loop_
_atom_site_type_symbol
_atom_site_label
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
P P1 0.68100(5) 0.55081(12) 0.00469(10) 0.0475(5) Uani d . 1 A 4
F F5 0.68700(12) 0.5420(3) 0.1168(2) 0.0838(12) Uani d . 1 A 4
F F6 0.67505(14) 0.5567(3) -0.1073(2) 0.0931(13) Uani d . 1 A 4
N N3 0.97199(17) 0.6798(4) 0.8551(3) 0.0387(11) Uani d . 1 B 4
N N2 0.87331(15) 0.7780(3) 0.7772(3) 0.0339(11) Uani d . 1 B 4
C C1 0.8558(2) 0.7028(4) 0.8282(4) 0.0394(13) Uani d . 1 B 4
H H1 0.8727 0.683 0.8922 0.047 Uiso calc R 1 B 4
N N1 0.81084(16) 0.6595(3) 0.7753(3) 0.0384(11) Uani d . 1 B 4
C C13 1.0420(3) 0.3015(5) 0.8984(4) 0.0642(17) Uani d . 1 B 4
H H13 1.0485 0.2248 0.9066 0.077 Uiso calc R 1 B 4
C C12 1.0831(2) 0.3723(5) 0.8954(4) 0.0596(16) Uani d . 1 B 4
H H14 1.1175 0.3444 0.9007 0.072 Uiso calc R 1 B 4
C C11 1.0732(2) 0.4849(5) 0.8846(4) 0.0508(15) Uani d . 1 B 4
H H15 1.1011 0.5337 0.8826 0.061 Uiso calc R 1 B 4
C C10 1.0231(2) 0.5258(5) 0.8766(3) 0.0394(13) Uani d . 1 B 4
N N4 1.01857(17) 0.6434(4) 0.8696(3) 0.0411(11) Uani d . 1 B 4
C C5 0.9693(2) 0.7975(4) 0.8511(3) 0.0383(13) Uani d . 1 B 4
C C4 0.9202(2) 0.8455(4) 0.8122(4) 0.0390(13) Uani d . 1 B 4
C C16 0.77754(19) 0.5753(4) 0.8075(4) 0.0505(15) Uani d . 1 B 4
H H16A 0.7433 0.5686 0.7588 0.061 Uiso calc R 1 B 4
H H16B 0.7702 0.6004 0.8676 0.061 Uiso calc R 1 B 4
C C17 0.80392(17) 0.4630(4) 0.8236(4) 0.0379(13) Uani d . 1 B 4
C C22 0.8217(2) 0.4214(5) 0.9145(4) 0.0530(15) Uani d . 1 B 4
H H22 0.8189 0.4647 0.9673 0.064 Uiso calc R 1 B 4
C C21 0.8439(2) 0.3164(6) 0.9300(5) 0.0664(17) Uani d . 1 B 4
H H21 0.8562 0.289 0.9932 0.08 Uiso calc R 1 B 4
C C20 0.8480(2) 0.2530(5) 0.8542(6) 0.0623(18) Uani d . 1 B 4
H H20 0.8628 0.1814 0.8648 0.075 Uiso calc R 1 B 4
C C14 0.9917(2) 0.3421(5) 0.8896(4) 0.0654(17) Uani d . 1 B 4
H H12 0.9637 0.2931 0.8907 0.078 Uiso calc R 1 B 4
C C15 0.9819(2) 0.4541(5) 0.8791(4) 0.0515(15) Uani d . 1 B 4
H H11 0.9474 0.4817 0.8736 0.062 Uiso calc R 1 B 4
C C6 1.0131(2) 0.8665(5) 0.8857(4) 0.0520(15) Uani d . 1 B 4
H H6 1.0468 0.8357 0.9145 0.062 Uiso calc R 1 B 4
C C7 1.0070(2) 0.9793(6) 0.8777(5) 0.0689(18) Uani d . 1 B 4
H H7 1.0367 1.0256 0.9017 0.083 Uiso calc R 1 B 4
C C8 0.9582(3) 1.0260(5) 0.8351(5) 0.0686(18) Uani d . 1 B 4
H H8 0.9549 1.1035 0.8285 0.082 Uiso calc R 1 B 4
C C9 0.9142(2) 0.9589(5) 0.8024(4) 0.0524(15) Uani d . 1 B 4
H H9 0.8806 0.9901 0.7737 0.063 Uiso calc R 1 B 4
C C19 0.8304(2) 0.2934(6) 0.7626(5) 0.0616(17) Uani d . 1 B 4
H H19 0.8333 0.2498 0.71 0.074 Uiso calc R 1 B 4
C C18 0.8084(2) 0.3986(5) 0.7471(4) 0.0542(16) Uani d . 1 B 4
H H18 0.7964 0.4263 0.6839 0.065 Uiso calc R 1 B 4
C C3 0.7990(2) 0.7106(5) 0.6879(4) 0.0521(15) Uani d . 1 B 4
H H2 0.769 0.6967 0.6362 0.062 Uiso calc R 1 B 4
C C2 0.8376(2) 0.7841(5) 0.6887(4) 0.0489(15) Uani d . 1 B 4
H H3 0.8398 0.8312 0.6378 0.059 Uiso calc R 1 B 4
F F1 0.7259(2) 0.6353(5) 0.0214(3) 0.179(3) Uani d . 1 A 4
F F2 0.63596(19) 0.6370(4) -0.0044(3) 0.1414(19) Uani d . 1 A 4
F F3 0.63623(13) 0.4578(3) -0.0156(3) 0.0894(12) Uani d . 1 A 4
F F4 0.72241(17) 0.4555(4) 0.0146(3) 0.1359(18) Uani d . 1 A 4

loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_12
_atom_site_aniso_U_13
_atom_site_aniso_U_23
P1 0.0392(9) 0.0506(11) 0.0485(11) -0.0002(8) 0.0041(7) 0.0070(7)
F5 0.069(2) 0.131(3) 0.048(2) -0.001(2) 0.0102(17) 0.006(2)
F6 0.098(3) 0.131(3) 0.046(2) -0.035(2) 0.0106(19) 0.011(2)
N3 0.032(3) 0.042(3) 0.038(3) 0.003(2) 0.002(2) -0.003(2)
N2 0.031(3) 0.028(3) 0.044(3) -0.003(2) 0.012(3) 0.004(2)
C1 0.028(3) 0.043(3) 0.042(3) 0.006(3) 0.000(3) -0.002(3)
N1 0.026(3) 0.034(3) 0.050(3) 0.002(2) 0.001(2) 0.002(2)
C13 0.067(5) 0.042(4) 0.074(5) 0.012(4) 0.001(3) -0.003(3)
C12 0.053(4) 0.059(5) 0.063(4) 0.016(4) 0.008(3) -0.002(3)
C11 0.041(4) 0.054(5) 0.053(4) 0.004(3) 0.005(3) -0.006(3)
C10 0.035(4) 0.046(4) 0.031(3) 0.006(3) -0.003(2) -0.002(3)
N4 0.035(3) 0.045(3) 0.040(3) 0.005(2) 0.002(2) -0.002(2)
C5 0.036(4) 0.036(4) 0.043(3) -0.001(3) 0.010(3) -0.007(3)
C4 0.036(4) 0.033(4) 0.050(3) -0.007(3) 0.016(3) -0.007(3)
C16 0.029(3) 0.040(4) 0.082(4) -0.003(3) 0.012(3) 0.007(3)
C17 0.020(3) 0.042(4) 0.049(4) -0.006(2) 0.005(3) -0.001(3)
C22 0.054(4) 0.053(4) 0.051(5) 0.001(3) 0.011(3) -0.005(3)
C21 0.068(4) 0.064(5) 0.066(5) 0.013(4) 0.016(3) 0.020(4)
C20 0.050(4) 0.042(4) 0.102(6) 0.006(3) 0.033(4) 0.014(5)
C14 0.060(5) 0.044(5) 0.085(5) -0.001(3) 0.007(3) 0.001(3)
C15 0.036(4) 0.050(5) 0.062(4) 0.001(3) 0.002(3) -0.002(3)
C6 0.035(4) 0.048(4) 0.069(4) -0.005(3) 0.007(3) -0.011(3)
C7 0.045(4) 0.054(5) 0.105(5) -0.015(3) 0.014(4) -0.020(4)
C8 0.051(4) 0.037(4) 0.116(6) -0.007(4) 0.018(4) -0.009(4)
C9 0.038(4) 0.038(4) 0.082(4) 0.000(3) 0.017(3) -0.006(3)
C19 0.067(4) 0.054(5) 0.073(5) -0.012(4) 0.034(4) -0.013(4)
C18 0.052(4) 0.053(4) 0.057(4) -0.007(3) 0.013(3) 0.004(4)
C3 0.036(4) 0.058(4) 0.051(4) -0.003(3) -0.009(3) 0.010(3)
C2 0.044(4) 0.055(4) 0.039(4) -0.001(3) -0.004(3) 0.013(3)
F1 0.202(5) 0.225(6) 0.084(3) -0.175(5) -0.013(3) 0.020(3)
F2 0.171(4) 0.117(4) 0.113(4) 0.095(3) -0.004(3) -0.007(3)
F3 0.081(2) 0.099(3) 0.082(3) -0.038(2) 0.0099(19) 0.006(2)
F4 0.106(3) 0.181(5) 0.125(4) 0.088(3) 0.038(3) 0.026(3)

_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_site_symmetry_2
_geom_bond_distance
_geom_bond_publ_flag
P1 F1 . 1.518(4) ?
P1 F2 . 1.543(4) ?
P1 F4 . 1.553(4) ?
P1 F6 . 1.578(3) ?
P1 F5 . 1.582(3) ?
P1 F3 . 1.585(3) ?
N3 N4 . 1.251(5) ?
N3 C5 . 1.419(6) ?
N2 C1 . 1.319(6) ?
N2 C2 . 1.365(6) ?
N2 C4 . 1.440(6) ?
C1 N1 . 1.321(6) ?
C1 H1 . 0.94 ?
N1 C3 . 1.360(6) ?
N1 C16 . 1.483(6) ?
C13 C14 . 1.367(7) ?
C13 C12 . 1.376(8) ?
C13 H13 . 0.94 ?
C12 C11 . 1.380(7) ?
C12 H14 . 0.94 ?
C11 C10 . 1.368(7) ?
C11 H15 . 0.94 ?
C10 C15 . 1.381(7) ?
C10 N4 . 1.422(6) ?
C5 C4 . 1.378(6) ?
C5 C6 . 1.389(7) ?
C4 C9 . 1.378(7) ?
C16 C17 . 1.506(7) ?
C16 H16A . 0.98 ?
C16 H16B . 0.98 ?
C17 C22 . 1.362(7) ?
C17 C18 . 1.374(7) ?
C22 C21 . 1.383(8) ?
C22 H22 . 0.94 ?
C21 C20 . 1.358(8) ?
C21 H21 . 0.94 ?
C20 C19 . 1.365(8) ?
C20 H20 . 0.94 ?
C14 C15 . 1.373(7) ?
C14 H12 . 0.94 ?
C15 H11 . 0.94 ?
C6 C7 . 1.368(8) ?
C6 H6 . 0.94 ?
C7 C8 . 1.376(8) ?
C7 H7 . 0.94 ?
C8 C9 . 1.378(7) ?
C8 H8 . 0.94 ?
C9 H9 . 0.94 ?
C19 C18 . 1.384(8) ?
C19 H19 . 0.94 ?
C18 H18 . 0.94 ?
C3 C2 . 1.334(7) ?
C3 H2 . 0.94 ?
C2 H3 . 0.94 ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle
_geom_angle_publ_flag
F1 P1 F2 . . 95.5(4) ?
F1 P1 F4 . . 89.8(3) ?
F2 P1 F4 . . 174.6(3) ?
F1 P1 F6 . . 89.8(2) ?
F2 P1 F6 . . 90.8(2) ?
F4 P1 F6 . . 90.4(2) ?
F1 P1 F5 . . 91.0(2) ?
F2 P1 F5 . . 90.1(2) ?
F4 P1 F5 . . 88.6(2) ?
F6 P1 F5 . . 178.8(2) ?
F1 P1 F3 . . 176.5(3) ?
F2 P1 F3 . . 87.5(3) ?
F4 P1 F3 . . 87.2(3) ?
F6 P1 F3 . . 88.49(19) ?
F5 P1 F3 . . 90.66(19) ?
N4 N3 C5 . . 113.0(4) ?
C1 N2 C2 . . 107.8(4) ?
C1 N2 C4 . . 125.2(4) ?
C2 N2 C4 . . 126.9(5) ?
N2 C1 N1 . . 109.4(4) ?
N2 C1 H1 . . 125.3 ?
N1 C1 H1 . . 125.3 ?
C1 N1 C3 . . 107.7(4) ?
C1 N1 C16 . . 126.1(5) ?
C3 N1 C16 . . 126.1(5) ?
C14 C13 C12 . . 120.2(5) ?
C14 C13 H13 . . 119.9 ?
C12 C13 H13 . . 119.9 ?
C13 C12 C11 . . 119.3(5) ?
C13 C12 H14 . . 120.3 ?
C11 C12 H14 . . 120.3 ?
C10 C11 C12 . . 120.5(5) ?
C10 C11 H15 . . 119.7 ?
C12 C11 H15 . . 119.7 ?
C11 C10 C15 . . 119.8(5) ?
C11 C10 N4 . . 115.1(5) ?
C15 C10 N4 . . 125.1(5) ?
N3 N4 C10 . . 114.7(4) ?
C4 C5 C6 . . 118.5(5) ?
C4 C5 N3 . . 117.7(5) ?
C6 C5 N3 . . 123.7(5) ?
C9 C4 C5 . . 121.7(5) ?
C9 C4 N2 . . 117.4(5) ?
C5 C4 N2 . . 120.9(5) ?
N1 C16 C17 . . 112.5(4) ?
N1 C16 H16A . . 109.1 ?
C17 C16 H16A . . 109.1 ?
N1 C16 H16B . . 109.1 ?
C17 C16 H16B . . 109.1 ?
H16A C16 H16B . . 107.8 ?
C22 C17 C18 . . 118.8(5) ?
C22 C17 C16 . . 120.2(5) ?
C18 C17 C16 . . 120.9(5) ?
C17 C22 C21 . . 120.9(5) ?
C17 C22 H22 . . 119.6 ?
C21 C22 H22 . . 119.6 ?
C20 C21 C22 . . 120.1(6) ?
C20 C21 H21 . . 119.9 ?
C22 C21 H21 . . 119.9 ?
C21 C20 C19 . . 119.8(6) ?
C21 C20 H20 . . 120.1 ?
C19 C20 H20 . . 120.1 ?
C13 C14 C15 . . 120.4(6) ?
C13 C14 H12 . . 119.8 ?
C15 C14 H12 . . 119.8 ?
C14 C15 C10 . . 119.6(5) ?
C14 C15 H11 . . 120.2 ?
C10 C15 H11 . . 120.2 ?
C7 C6 C5 . . 119.9(5) ?
C7 C6 H6 . . 120.1 ?
C5 C6 H6 . . 120.1 ?
C6 C7 C8 . . 121.0(5) ?
C6 C7 H7 . . 119.5 ?
C8 C7 H7 . . 119.5 ?
C7 C8 C9 . . 119.9(5) ?
C7 C8 H8 . . 120.1 ?
C9 C8 H8 . . 120.1 ?
C4 C9 C8 . . 119.0(5) ?
C4 C9 H9 . . 120.5 ?
C8 C9 H9 . . 120.5 ?
C20 C19 C18 . . 120.1(6) ?
C20 C19 H19 . . 119.9 ?
C18 C19 H19 . . 119.9 ?
C17 C18 C19 . . 120.3(5) ?
C17 C18 H18 . . 119.8 ?
C19 C18 H18 . . 119.8 ?
C2 C3 N1 . . 107.8(4) ?
C2 C3 H2 . . 126.1 ?
N1 C3 H2 . . 126.1 ?
C3 C2 N2 . . 107.3(4) ?
C3 C2 H3 . . 126.3 ?
N2 C2 H3 . . 126.3 ?

_database_code_depnum_ccdc_archive 'CCDC 944154'
#######################################################################
#
#                 Cambridge Crystallographic Data Centre
#                                CCDC 
# 
#######################################################################
# 
#  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.
#
#  This CIF is provided on the understanding that it is used for bona
#  fide research purposes only. It may contain copyright material
#  of the CCDC or of third parties, and may not be copied or further
#  disseminated in any form, whether machine-readable or not,
#  except for the purpose of generating routine backup copies
#  on your local computer system.
# 
#  For further information on the CCDC, data deposition and
#  data retrieval see:
#                         www.ccdc.cam.ac.uk
#
#  Bona fide researchers may freely download Mercury and enCIFer
#  from this site to visualise CIF-encoded structures and 
#  to carry out CIF format checking respectively.
#
data_I
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C22 H18 Au Cl N4'
_chemical_formula_iupac          ?
_chemical_formula_weight         570.82

_chemical_melting_point          ?

_space_group_crystal_system      monoclinic
_space_group_name_H-M_alt        'P 1 21/c 1'
_space_group_name_Hall           '-P 2ybc'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'

_cell_length_a                   12.734(3)
_cell_length_b                   13.625(2)
_cell_length_c                   12.379(3)
_cell_angle_alpha                90
_cell_angle_beta                 111.712(7)
_cell_angle_gamma                90
_cell_volume                     1995.4(7)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    6121
_cell_measurement_theta_min      2.2767
_cell_measurement_theta_max      24.4289
_cell_measurement_temperature    205.(2)

_exptl_crystal_description       platelet
_exptl_crystal_colour            orange
_exptl_crystal_size_max          0.490
_exptl_crystal_size_mid          0.260
_exptl_crystal_size_min          0.130
_exptl_crystal_density_diffrn    1.900
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1096

_exptl_absorpt_coefficient_mu    7.522
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS V2012/1 (Bruker AXS Inc.)'
_exptl_absorpt_correction_T_min  0.12
_exptl_absorpt_correction_T_max  0.44

_exptl_special_details           
;
The largest residual peak of 3.64 is near the gold atom.
coordinates:  0.468500   0.192000   0.861100
coordinates gold atom: 0.457291   0.114675   0.848457
;

_diffrn_ambient_temperature      205.(2)

_diffrn_source                   ?
_diffrn_source_type              ?

_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_source         'sealed MicroFocus tube'
_diffrn_radiation_monochromator  'doubly curved silicon crystal'

_diffrn_measurement_device_type  'SMART X2S'
_diffrn_measurement_method       omega-scan

_diffrn_detector_area_resol_mean ?

_diffrn_reflns_number            27343
_diffrn_reflns_av_R_equivalents  0.0780
_diffrn_reflns_av_sigmaI/netI    0.0582
_diffrn_reflns_theta_min         2.47
_diffrn_reflns_theta_max         28.33
_diffrn_reflns_theta_full        28.33
_diffrn_measured_fraction_theta_max 0.977
_diffrn_measured_fraction_theta_full 0.977
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_k_min       -18
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_limit_l_max       16

_refine_special_details          
;
Refinement of F^2^ against ALL reflections.  The weighted R-factor wR and
goodness of fit S are based on F^2^, conventional R-factors R are based
on F, with F set to zero for negative F^2^. The threshold expression of
F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is
not relevant to the choice of reflections for refinement.  R-factors based
on F^2^ are statistically about twice as large as those based on F, and R-
factors based on ALL data will be even larger.
;

_reflns_number_total             4854
_reflns_number_gt                3644
_reflns_threshold_expression     >2sigma(I)

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_R_factor_all          0.0618
_refine_ls_R_factor_gt           0.0405
_refine_ls_wR_factor_gt          0.0974
_refine_ls_wR_factor_ref         0.1063
_refine_ls_goodness_of_fit_ref   1.058
_refine_ls_restrained_S_all      1.058
_refine_ls_number_reflns         4854
_refine_ls_number_parameters     253
_refine_ls_number_restraints     0
_refine_ls_hydrogen_treatment    constr
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[\s^2^(Fo^2^)+(0.0437P)^2^+3.9493P] where P=(Fo^2^+2Fc^2^)/3'

_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap

_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_diff_density_max         3.641
_refine_diff_density_min         -1.090
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?

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'

_computing_data_collection       'APEX2 Version 2009.9 (Bruker)'
_computing_cell_refinement       'SAINT V8.27B (Bruker AXS Inc., 2012)'
_computing_data_reduction        'SAINT V8.27B (Bruker AXS Inc., 2012)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_molecular_graphics    
'ORTEP-3 for Windows version 2.02 (Farrugia, 1997)'
_computing_publication_material  'SHELXL-97 and publCIF'

loop_
_atom_site_type_symbol
_atom_site_label
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Au Au1 0.45729(2) 0.114675(17) 0.84846(2) 0.03362(10) Uani d . 1 . .
Cl Cl1 0.50476(16) -0.02753(12) 0.78077(15) 0.0463(4) Uani d . 1 . .
N N2 0.3227(5) 0.2966(4) 0.8259(4) 0.0365(12) Uani d . 1 . .
N N3 0.0492(5) 0.2005(4) 0.3691(4) 0.0427(14) Uani d . 1 . .
N N4 -0.0231(5) 0.1333(4) 0.3517(5) 0.0411(14) Uani d . 1 . .
N N1 0.4532(5) 0.2911(4) 0.9944(4) 0.0385(13) Uani d . 1 . .
C C1 0.4086(6) 0.2391(5) 0.8950(5) 0.0359(14) Uani d . 1 . .
C C5 0.2517(6) 0.2695(5) 0.7097(5) 0.0358(14) Uani d . 1 . .
C C6 0.1956(6) 0.1814(5) 0.6901(5) 0.0380(15) Uani d . 1 . .
H H9 0.2033 0.139 0.7525 0.046 Uiso calc R 1 . .
C C7 0.1277(6) 0.1553(5) 0.5782(6) 0.0391(15) Uani d . 1 . .
H H8 0.0903 0.0944 0.564 0.047 Uiso calc R 1 . .
C C8 0.1148(5) 0.2189(5) 0.4865(6) 0.0365(15) Uani d . 1 . .
C C9 -0.0856(6) 0.1147(5) 0.2317(6) 0.0387(15) Uani d . 1 . .
C C14 -0.0509(8) 0.1466(8) 0.1435(7) 0.074(3) Uani d . 1 . .
H H5 0.0173 0.1812 0.1618 0.089 Uiso calc R 1 . .
C C13 -0.1158(10) 0.1274(9) 0.0310(8) 0.093(4) Uani d . 1 . .
H H4 -0.0911 0.1467 -0.0286 0.112 Uiso calc R 1 . .
C C12 -0.2198(7) 0.0789(6) 0.0033(6) 0.0521(19) Uani d . 1 . .
H H3 -0.2651 0.0663 -0.0748 0.063 Uiso calc R 1 . .
C C11 -0.2537(7) 0.0510(5) 0.0880(6) 0.0455(17) Uani d . 1 . .
H H2 -0.3238 0.0194 0.0697 0.055 Uiso calc R 1 . .
C C10 -0.1857(7) 0.0683(5) 0.2040(6) 0.0486(18) Uani d . 1 . .
H H1 -0.2099 0.0475 0.2634 0.058 Uiso calc R 1 . .
C C15 0.1721(7) 0.3080(5) 0.5086(6) 0.0475(18) Uani d . 1 . .
H H7 0.1648 0.3511 0.447 0.057 Uiso calc R 1 . .
C C16 0.2399(6) 0.3334(5) 0.6213(6) 0.0461(18) Uani d . 1 . .
H H6 0.2775 0.3942 0.6366 0.055 Uiso calc R 1 . .
C C3 0.3162(7) 0.3824(5) 0.8814(6) 0.0448(18) Uani d . 1 . .
H H10 0.2649 0.4342 0.8508 0.054 Uiso calc R 1 . .
C C2 0.3969(7) 0.3780(5) 0.9871(6) 0.0450(17) Uani d . 1 . .
H H18 0.4123 0.4257 1.0459 0.054 Uiso calc R 1 . .
C C17 0.5532(6) 0.2624(5) 1.0957(5) 0.0440(17) Uani d . 1 . .
H H17 0.5653 0.1916 1.0927 0.053 Uiso calc R 1 . .
H H16 0.5394 0.2763 1.1669 0.053 Uiso calc R 1 . .
C C18 0.6578(6) 0.3158(5) 1.0997(5) 0.0372(15) Uani d . 1 . .
C C23 0.6738(9) 0.3501(6) 1.0029(7) 0.061(2) Uani d . 1 . .
H H15 0.6156 0.3426 0.9298 0.073 Uiso calc R 1 . .
C C22 0.7711(10) 0.3947(7) 1.0097(9) 0.073(3) Uani d . 1 . .
H H14 0.781 0.4153 0.9416 0.088 Uiso calc R 1 . .
C C21 0.8553(9) 0.4098(6) 1.1163(11) 0.070(3) Uani d . 1 . .
H H13 0.9214 0.4434 1.1215 0.085 Uiso calc R 1 . .
C C20 0.8433(8) 0.3766(6) 1.2127(9) 0.071(3) Uani d . 1 . .
H H12 0.9024 0.3846 1.2851 0.085 Uiso calc R 1 . .
C C19 0.7433(7) 0.3299(5) 1.2062(6) 0.0500(19) Uani d . 1 . .
H H11 0.7345 0.3081 1.2745 0.06 Uiso calc R 1 . .

loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_12
_atom_site_aniso_U_13
_atom_site_aniso_U_23
Au1 0.03268(16) 0.03388(15) 0.03052(14) 0.00252(11) 0.00726(10) -0.00107(10)
Cl1 0.0491(11) 0.0392(9) 0.0473(9) 0.0090(8) 0.0140(8) -0.0084(7)
N2 0.040(3) 0.035(3) 0.028(3) 0.002(3) 0.006(2) -0.007(2)
N3 0.044(4) 0.050(3) 0.029(3) -0.005(3) 0.008(3) -0.001(3)
N4 0.040(4) 0.047(4) 0.032(3) -0.001(3) 0.008(3) -0.005(2)
N1 0.037(3) 0.039(3) 0.032(3) 0.004(3) 0.004(2) -0.005(2)
C1 0.036(4) 0.036(3) 0.030(3) -0.005(3) 0.006(3) -0.004(3)
C5 0.032(4) 0.039(4) 0.032(3) 0.001(3) 0.008(3) -0.006(3)
C6 0.039(4) 0.039(4) 0.031(3) 0.002(3) 0.008(3) 0.002(3)
C7 0.037(4) 0.038(4) 0.038(3) -0.001(3) 0.010(3) -0.003(3)
C8 0.025(3) 0.045(4) 0.037(3) -0.001(3) 0.008(3) 0.001(3)
C9 0.035(4) 0.039(4) 0.033(3) 0.003(3) 0.003(3) -0.003(3)
C14 0.059(6) 0.120(8) 0.045(4) -0.046(6) 0.021(4) -0.022(5)
C13 0.084(8) 0.159(11) 0.036(4) -0.073(7) 0.021(5) -0.015(5)
C12 0.058(5) 0.053(4) 0.034(4) -0.009(4) 0.004(4) -0.005(3)
C11 0.046(5) 0.039(4) 0.047(4) -0.016(3) 0.013(3) -0.007(3)
C10 0.058(5) 0.047(4) 0.046(4) -0.016(4) 0.027(4) 0.000(3)
C15 0.052(5) 0.047(4) 0.036(4) -0.006(4) 0.008(3) 0.005(3)
C16 0.046(5) 0.035(4) 0.043(4) -0.009(3) -0.001(3) 0.003(3)
C3 0.056(5) 0.035(4) 0.041(4) 0.018(3) 0.015(3) -0.002(3)
C2 0.050(5) 0.038(4) 0.044(4) 0.000(3) 0.014(3) -0.011(3)
C17 0.051(5) 0.049(4) 0.024(3) -0.001(3) 0.004(3) 0.006(3)
C18 0.044(4) 0.032(3) 0.032(3) 0.005(3) 0.009(3) -0.001(3)
C23 0.084(7) 0.061(5) 0.036(4) -0.019(5) 0.021(4) -0.007(4)
C22 0.097(9) 0.078(7) 0.071(6) -0.020(6) 0.061(7) -0.006(5)
C21 0.055(6) 0.050(5) 0.123(9) 0.000(4) 0.052(6) 0.002(5)
C20 0.046(6) 0.065(6) 0.080(7) -0.001(4) -0.003(5) 0.009(5)
C19 0.052(5) 0.048(4) 0.038(4) -0.005(4) 0.003(3) 0.000(3)

_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_site_symmetry_2
_geom_bond_distance
_geom_bond_publ_flag
Au1 C1 . 1.963(6) ?
Au1 Cl1 . 2.2794(16) ?
N2 C1 . 1.360(8) ?
N2 C3 . 1.375(8) ?
N2 C5 . 1.435(8) ?
N3 N4 . 1.259(8) ?
N3 C8 . 1.406(8) ?
N4 C9 . 1.424(8) ?
N1 C1 . 1.350(8) ?
N1 C2 . 1.370(8) ?
N1 C17 . 1.472(8) ?
C5 C16 . 1.362(9) ?
C5 C6 . 1.373(9) ?
C6 C7 . 1.381(9) ?
C6 H9 . 0.94 ?
C7 C8 . 1.388(9) ?
C7 H8 . 0.94 ?
C8 C15 . 1.391(10) ?
C9 C10 . 1.349(10) ?
C9 C14 . 1.390(11) ?
C14 C13 . 1.356(11) ?
C14 H5 . 0.94 ?
C13 C12 . 1.404(12) ?
C13 H4 . 0.94 ?
C12 C11 . 1.330(10) ?
C12 H3 . 0.94 ?
C11 C10 . 1.395(10) ?
C11 H2 . 0.94 ?
C10 H1 . 0.94 ?
C15 C16 . 1.385(9) ?
C15 H7 . 0.94 ?
C16 H6 . 0.94 ?
C3 C2 . 1.333(10) ?
C3 H10 . 0.94 ?
C2 H18 . 0.94 ?
C17 C18 . 1.502(10) ?
C17 H17 . 0.98 ?
C17 H16 . 0.98 ?
C18 C23 . 1.369(10) ?
C18 C19 . 1.378(9) ?
C23 C22 . 1.355(13) ?
C23 H15 . 0.94 ?
C22 C21 . 1.373(14) ?
C22 H14 . 0.94 ?
C21 C20 . 1.336(14) ?
C21 H13 . 0.94 ?
C20 C19 . 1.399(12) ?
C20 H12 . 0.94 ?
C19 H11 . 0.94 ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle
_geom_angle_publ_flag
C1 Au1 Cl1 . . 175.76(19) ?
C1 N2 C3 . . 111.0(5) ?
C1 N2 C5 . . 122.9(5) ?
C3 N2 C5 . . 126.0(6) ?
N4 N3 C8 . . 115.1(5) ?
N3 N4 C9 . . 113.5(6) ?
C1 N1 C2 . . 111.2(6) ?
C1 N1 C17 . . 125.2(6) ?
C2 N1 C17 . . 123.5(6) ?
N1 C1 N2 . . 103.9(5) ?
N1 C1 Au1 . . 130.5(5) ?
N2 C1 Au1 . . 125.5(4) ?
C16 C5 C6 . . 121.4(6) ?
C16 C5 N2 . . 118.9(6) ?
C6 C5 N2 . . 119.7(6) ?
C5 C6 C7 . . 119.6(6) ?
C5 C6 H9 . . 120.2 ?
C7 C6 H9 . . 120.2 ?
C6 C7 C8 . . 120.0(6) ?
C6 C7 H8 . . 120.0 ?
C8 C7 H8 . . 120.0 ?
C7 C8 C15 . . 119.3(6) ?
C7 C8 N3 . . 125.4(6) ?
C15 C8 N3 . . 115.3(6) ?
C10 C9 C14 . . 119.5(7) ?
C10 C9 N4 . . 117.4(7) ?
C14 C9 N4 . . 123.1(7) ?
C13 C14 C9 . . 119.8(8) ?
C13 C14 H5 . . 120.1 ?
C9 C14 H5 . . 120.1 ?
C14 C13 C12 . . 120.2(8) ?
C14 C13 H4 . . 119.9 ?
C12 C13 H4 . . 119.9 ?
C11 C12 C13 . . 119.6(7) ?
C11 C12 H3 . . 120.2 ?
C13 C12 H3 . . 120.2 ?
C12 C11 C10 . . 120.3(7) ?
C12 C11 H2 . . 119.8 ?
C10 C11 H2 . . 119.8 ?
C9 C10 C11 . . 120.6(7) ?
C9 C10 H1 . . 119.7 ?
C11 C10 H1 . . 119.7 ?
C16 C15 C8 . . 120.1(6) ?
C16 C15 H7 . . 119.9 ?
C8 C15 H7 . . 119.9 ?
C5 C16 C15 . . 119.5(6) ?
C5 C16 H6 . . 120.3 ?
C15 C16 H6 . . 120.3 ?
C2 C3 N2 . . 106.6(6) ?
C2 C3 H10 . . 126.7 ?
N2 C3 H10 . . 126.7 ?
C3 C2 N1 . . 107.3(6) ?
C3 C2 H18 . . 126.3 ?
N1 C2 H18 . . 126.3 ?
N1 C17 C18 . . 112.2(5) ?
N1 C17 H17 . . 109.2 ?
C18 C17 H17 . . 109.2 ?
N1 C17 H16 . . 109.2 ?
C18 C17 H16 . . 109.2 ?
H17 C17 H16 . . 107.9 ?
C23 C18 C19 . . 118.0(7) ?
C23 C18 C17 . . 123.5(6) ?
C19 C18 C17 . . 118.4(6) ?
C22 C23 C18 . . 121.8(8) ?
C22 C23 H15 . . 119.1 ?
C18 C23 H15 . . 119.1 ?
C23 C22 C21 . . 119.8(8) ?
C23 C22 H14 . . 120.1 ?
C21 C22 H14 . . 120.1 ?
C20 C21 C22 . . 120.1(9) ?
C20 C21 H13 . . 120.0 ?
C22 C21 H13 . . 120.0 ?
C21 C20 C19 . . 120.4(9) ?
C21 C20 H12 . . 119.8 ?
C19 C20 H12 . . 119.8 ?
C18 C19 C20 . . 119.8(8) ?
C18 C19 H11 . . 120.1 ?
C20 C19 H11 . . 120.1 ?

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_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion
_geom_torsion_publ_flag
C8 N3 N4 C9 . . . . -178.2(6) ?
C2 N1 C1 N2 . . . . -0.1(8) ?
C17 N1 C1 N2 . . . . -176.7(6) ?
C2 N1 C1 Au1 . . . . 175.6(5) ?
C17 N1 C1 Au1 . . . . -1.0(11) ?
C3 N2 C1 N1 . . . . 0.9(8) ?
C5 N2 C1 N1 . . . . 179.5(6) ?
C3 N2 C1 Au1 . . . . -175.0(5) ?
C5 N2 C1 Au1 . . . . 3.6(9) ?
Cl1 Au1 C1 N1 . . . . -168.(2) ?
Cl1 Au1 C1 N2 . . . . 7.(3) ?
C1 N2 C5 C16 . . . . -126.3(7) ?
C3 N2 C5 C16 . . . . 52.2(10) ?
C1 N2 C5 C6 . . . . 55.1(9) ?
C3 N2 C5 C6 . . . . -126.5(8) ?
C16 C5 C6 C7 . . . . 1.6(11) ?
N2 C5 C6 C7 . . . . -179.7(6) ?
C5 C6 C7 C8 . . . . -1.3(11) ?
C6 C7 C8 C15 . . . . 1.0(11) ?
C6 C7 C8 N3 . . . . 179.4(7) ?
N4 N3 C8 C7 . . . . 18.2(10) ?
N4 N3 C8 C15 . . . . -163.4(7) ?
N3 N4 C9 C10 . . . . -159.6(7) ?
N3 N4 C9 C14 . . . . 16.9(11) ?
C10 C9 C14 C13 . . . . -2.5(15) ?
N4 C9 C14 C13 . . . . -179.0(10) ?
C9 C14 C13 C12 . . . . 2.4(18) ?
C14 C13 C12 C11 . . . . -0.7(17) ?
C13 C12 C11 C10 . . . . -0.9(14) ?
C14 C9 C10 C11 . . . . 0.8(12) ?
N4 C9 C10 C11 . . . . 177.5(7) ?
C12 C11 C10 C9 . . . . 0.9(12) ?
C7 C8 C15 C16 . . . . -1.0(11) ?
N3 C8 C15 C16 . . . . -179.6(7) ?
C6 C5 C16 C15 . . . . -1.6(12) ?
N2 C5 C16 C15 . . . . 179.7(7) ?
C8 C15 C16 C5 . . . . 1.3(12) ?
C1 N2 C3 C2 . . . . -1.4(9) ?
C5 N2 C3 C2 . . . . 180.0(7) ?
N2 C3 C2 N1 . . . . 1.3(9) ?
C1 N1 C2 C3 . . . . -0.8(9) ?
C17 N1 C2 C3 . . . . 175.9(7) ?
C1 N1 C17 C18 . . . . 100.4(8) ?
C2 N1 C17 C18 . . . . -75.8(9) ?
N1 C17 C18 C23 . . . . -27.8(10) ?
N1 C17 C18 C19 . . . . 153.2(6) ?
C19 C18 C23 C22 . . . . 1.5(13) ?
C17 C18 C23 C22 . . . . -177.4(8) ?
C18 C23 C22 C21 . . . . -2.5(15) ?
C23 C22 C21 C20 . . . . 3.0(15) ?
C22 C21 C20 C19 . . . . -2.6(15) ?
C23 C18 C19 C20 . . . . -1.1(11) ?
C17 C18 C19 C20 . . . . 178.0(7) ?
C21 C20 C19 C18 . . . . 1.6(13) ?

_database_code_depnum_ccdc_archive 'CCDC 944155'