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

#######################################################################
#
#                 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        
2,6-Dimethyl-N-(2-pyridinylmethylene)phenylamine
_chemical_name_common            ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C14 H14 N2'
_chemical_formula_iupac          ?
_chemical_formula_weight         210.27

_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                   10.2806(13)
_cell_length_b                   11.5990(14)
_cell_length_c                   19.760(2)
_cell_angle_alpha                90
_cell_angle_beta                 97.596(4)
_cell_angle_gamma                90
_cell_volume                     2335.6(5)
_cell_formula_units_Z            8
_cell_measurement_reflns_used    3869
_cell_measurement_theta_min      2.66
_cell_measurement_theta_max      22.36
_cell_measurement_temperature    200.(2)

_exptl_crystal_description       cubic
_exptl_crystal_colour            yellow
_exptl_crystal_size_max          0.41
_exptl_crystal_size_mid          0.37
_exptl_crystal_size_min          0.32
_exptl_crystal_density_diffrn    1.196
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             896

_exptl_absorpt_coefficient_mu    0.072
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS V2008/1 (Bruker AXS)'
_exptl_absorpt_correction_T_min  0.97
_exptl_absorpt_correction_T_max  0.98

_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 8.3330

_diffrn_reflns_number            21615
_diffrn_reflns_av_R_equivalents  0.0554
_diffrn_reflns_av_sigmaI/netI    0.0373
_diffrn_reflns_theta_min         2.00
_diffrn_reflns_theta_max         23.07
_diffrn_reflns_theta_full        23.07
_diffrn_measured_fraction_theta_max 0.994
_diffrn_measured_fraction_theta_full 0.994
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_limit_l_max       21

_refine_special_details          
;
Refinement of F² against ALL reflections.  The weighted R-factor wR and
goodness of fit S are based on F², conventional R-factors R are based
on F, with F set to zero for negative F². The threshold expression of
F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is
not relevant to the choice of reflections for refinement.  R-factors based
on F² 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             3251
_reflns_number_gt                2277
_reflns_threshold_expression     >2sigma(I)

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_R_factor_all          0.0714
_refine_ls_R_factor_gt           0.0453
_refine_ls_wR_factor_gt          0.1123
_refine_ls_wR_factor_ref         0.1282
_refine_ls_goodness_of_fit_ref   1.028
_refine_ls_restrained_S_all      1.028
_refine_ls_number_reflns         3251
_refine_ls_number_parameters     293
_refine_ls_number_restraints     0
_refine_ls_hydrogen_treatment    constr
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0619P)²+0.4890P] where P=(Fo²+2Fc²)/3'

_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap

_refine_ls_shift/su_max          0.021
_refine_ls_shift/su_mean         0.000
_refine_diff_density_max         0.211
_refine_diff_density_min         -0.191
_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'

_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
N N1 0.54687(18) 0.56167(15) 0.11334(9) 0.0457(5) Uani d . 1 . .
N N2 0.78066(19) 0.77359(16) 0.17237(9) 0.0505(5) Uani d . 1 . .
N N3 0.05117(17) 0.16590(14) 0.10514(9) 0.0423(5) Uani d . 1 . .
N N4 0.27603(18) -0.04381(15) 0.17736(9) 0.0462(5) Uani d . 1 . .
C C1 0.4642(3) 0.2179(2) 0.15166(13) 0.0643(8) Uani d . 1 . .
H H1 0.4442 0.1394 0.1594 0.077 Uiso calc R 1 . .
C C2 0.5483(3) 0.2462(2) 0.10546(13) 0.0586(7) Uani d . 1 . .
H H2 0.5869 0.1867 0.0818 0.07 Uiso calc R 1 . .
C C3 0.5775(2) 0.36021(19) 0.09293(11) 0.0470(6) Uani d . 1 . .
C C4 0.5213(2) 0.44534(18) 0.12938(10) 0.0407(5) Uani d . 1 . .
C C5 0.6382(2) 0.61417(18) 0.14845(11) 0.0386(5) Uani d . 1 . .
H H5 0.6834 0.5771 0.1876 0.046 Uiso calc R 1 . .
C C6 0.6783(2) 0.73129(17) 0.13137(11) 0.0380(5) Uani d . 1 . .
C C7 0.6181(2) 0.7899(2) 0.07559(12) 0.0510(6) Uani d . 1 . .
H H7 0.5449 0.7572 0.0477 0.061 Uiso calc R 1 . .
C C8 0.6653(3) 0.8969(2) 0.06047(13) 0.0607(7) Uani d . 1 . .
H H8 0.6257 0.939 0.0219 0.073 Uiso calc R 1 . .
C C9 0.7700(2) 0.9411(2) 0.10214(13) 0.0573(7) Uani d . 1 . .
H H9 0.8047 1.0147 0.0933 0.069 Uiso calc R 1 . .
C C10 0.4096(3) 0.3039(2) 0.18644(12) 0.0586(7) Uani d . 1 . .
H H10 0.3519 0.2838 0.2184 0.07 Uiso calc R 1 . .
C C11 0.4361(2) 0.41826(19) 0.17633(11) 0.0481(6) Uani d . 1 . .
C C12 0.3739(3) 0.5094(2) 0.21526(12) 0.0656(7) Uani d . 1 . .
H H12A 0.2935 0.5371 0.1879 0.098 Uiso calc R 1 . .
H H12B 0.4352 0.5737 0.2252 0.098 Uiso calc R 1 . .
H H12C 0.3522 0.4768 0.2582 0.098 Uiso calc R 1 . .
C C13 0.8235(2) 0.8773(2) 0.15658(13) 0.0586(7) Uani d . 1 . .
H H13 0.8963 0.9089 0.1853 0.07 Uiso calc R 1 . .
C C14 0.6666(2) 0.3911(2) 0.04209(13) 0.0613(7) Uani d . 1 . .
H H14A 0.692 0.321 0.0195 0.092 Uiso calc R 1 . .
H H14B 0.7452 0.429 0.0654 0.092 Uiso calc R 1 . .
H H14C 0.6211 0.4436 0.008 0.092 Uiso calc R 1 . .
C C15 -0.0162(3) 0.5131(2) 0.14193(12) 0.0591(7) Uani d . 1 . .
H H15 -0.0309 0.5925 0.15 0.071 Uiso calc R 1 . .
C C16 0.0564(2) 0.48054(19) 0.09133(12) 0.0531(6) Uani d . 1 . .
H H16 0.0908 0.5379 0.0643 0.064 Uiso calc R 1 . .
C C17 0.0800(2) 0.36570(18) 0.07938(11) 0.0433(6) Uani d . 1 . .
C C18 0.0279(2) 0.28365(17) 0.11982(10) 0.0396(5) Uani d . 1 . .
C C19 0.1344(2) 0.11218(17) 0.14588(11) 0.0382(5) Uani d . 1 . .
H H19 0.1716 0.1497 0.1866 0.046 Uiso calc R 1 . .
C C20 0.1762(2) -0.00558(17) 0.13317(10) 0.0356(5) Uani d . 1 . .
C C21 0.3219(2) -0.14846(19) 0.16562(12) 0.0529(6) Uani d . 1 . .
H H21 0.3937 -0.1769 0.1963 0.063 Uiso calc R 1 . .
C C22 0.2724(2) -0.2173(2) 0.11236(12) 0.0527(6) Uani d . 1 . .
H H22 0.3093 -0.291 0.1061 0.063 Uiso calc R 1 . .
C C23 -0.0672(2) 0.4311(2) 0.18048(12) 0.0555(7) Uani d . 1 . .
H H23 -0.1176 0.4546 0.215 0.067 Uiso calc R 1 . .
C C24 -0.0475(2) 0.31471(19) 0.17057(11) 0.0456(6) Uani d . 1 . .
C C25 -0.1077(3) 0.2264(2) 0.21242(12) 0.0640(7) Uani d . 1 . .
H H25A -0.0383 0.1866 0.2423 0.096 Uiso calc R 1 . .
H H25B -0.1572 0.1704 0.182 0.096 Uiso calc R 1 . .
H H25C -0.167 0.2647 0.2403 0.096 Uiso calc R 1 . .
C C26 0.1685(2) -0.1776(2) 0.06841(12) 0.0545(7) Uani d . 1 . .
H H26 0.131 -0.2236 0.0311 0.065 Uiso calc R 1 . .
C C27 0.1195(2) -0.07080(19) 0.07906(11) 0.0478(6) Uani d . 1 . .
H H27 0.0467 -0.0417 0.0493 0.057 Uiso calc R 1 . .
C C28 0.1629(2) 0.3301(2) 0.02612(12) 0.0550(7) Uani d . 1 . .
H H28A 0.1752 0.396 -0.0034 0.082 Uiso calc R 1 . .
H H28B 0.1193 0.2675 -0.0014 0.082 Uiso calc R 1 . .
H H28C 0.2486 0.3035 0.0483 0.082 Uiso calc R 1 . .


_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
N1 C5 . 1.250(3) ?
N1 C4 . 1.419(3) ?
N2 C13 . 1.333(3) ?
N2 C6 . 1.334(3) ?
N3 C19 . 1.259(2) ?
N3 C18 . 1.423(3) ?
N4 C20 . 1.333(3) ?
N4 C21 . 1.334(3) ?
C1 C10 . 1.373(3) ?
C1 C2 . 1.378(4) ?
C1 H1 . 0.95 ?
C2 C3 . 1.385(3) ?
C2 H2 . 0.95 ?
C3 C4 . 1.392(3) ?
C3 C14 . 1.490(3) ?
C4 C11 . 1.393(3) ?
C5 C6 . 1.472(3) ?
C5 H5 . 0.95 ?
C6 C7 . 1.371(3) ?
C7 C8 . 1.380(3) ?
C7 H7 . 0.95 ?
C8 C9 . 1.366(3) ?
C8 H8 . 0.95 ?
C9 C13 . 1.360(3) ?
C9 H9 . 0.95 ?
C10 C11 . 1.374(3) ?
C10 H10 . 0.95 ?
C11 C12 . 1.499(3) ?
C12 H12A . 0.98 ?
C12 H12B . 0.98 ?
C12 H12C . 0.98 ?
C13 H13 . 0.95 ?
C14 H14A . 0.98 ?
C14 H14B . 0.98 ?
C14 H14C . 0.98 ?
C15 C23 . 1.366(3) ?
C15 C16 . 1.378(3) ?
C15 H15 . 0.95 ?
C16 C17 . 1.380(3) ?
C16 H16 . 0.95 ?
C17 C18 . 1.395(3) ?
C17 C28 . 1.497(3) ?
C18 C24 . 1.393(3) ?
C19 C20 . 1.464(3) ?
C19 H19 . 0.95 ?
C20 C27 . 1.375(3) ?
C21 C22 . 1.365(3) ?
C21 H21 . 0.95 ?
C22 C26 . 1.364(3) ?
C22 H22 . 0.95 ?
C23 C24 . 1.383(3) ?
C23 H23 . 0.95 ?
C24 C25 . 1.500(3) ?
C25 H25A . 0.98 ?
C25 H25B . 0.98 ?
C25 H25C . 0.98 ?
C26 C27 . 1.365(3) ?
C26 H26 . 0.95 ?
C27 H27 . 0.95 ?
C28 H28A . 0.98 ?
C28 H28B . 0.98 ?
C28 H28C . 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
C5 N1 C4 . . 119.16(18) ?
C13 N2 C6 . . 116.7(2) ?
C19 N3 C18 . . 117.58(18) ?
C20 N4 C21 . . 116.65(19) ?
C10 C1 C2 . . 119.5(2) ?
C10 C1 H1 . . 120.3 ?
C2 C1 H1 . . 120.3 ?
C1 C2 C3 . . 121.1(2) ?
C1 C2 H2 . . 119.5 ?
C3 C2 H2 . . 119.5 ?
C2 C3 C4 . . 118.0(2) ?
C2 C3 C14 . . 121.1(2) ?
C4 C3 C14 . . 120.8(2) ?
C3 C4 C11 . . 121.7(2) ?
C3 C4 N1 . . 117.21(19) ?
C11 C4 N1 . . 121.0(2) ?
N1 C5 C6 . . 122.4(2) ?
N1 C5 H5 . . 118.8 ?
C6 C5 H5 . . 118.8 ?
N2 C6 C7 . . 122.8(2) ?
N2 C6 C5 . . 115.00(19) ?
C7 C6 C5 . . 122.1(2) ?
C6 C7 C8 . . 119.0(2) ?
C6 C7 H7 . . 120.5 ?
C8 C7 H7 . . 120.5 ?
C9 C8 C7 . . 118.6(2) ?
C9 C8 H8 . . 120.7 ?
C7 C8 H8 . . 120.7 ?
C13 C9 C8 . . 118.5(2) ?
C13 C9 H9 . . 120.8 ?
C8 C9 H9 . . 120.8 ?
C1 C10 C11 . . 121.8(2) ?
C1 C10 H10 . . 119.1 ?
C11 C10 H10 . . 119.1 ?
C10 C11 C4 . . 117.9(2) ?
C10 C11 C12 . . 120.0(2) ?
C4 C11 C12 . . 122.1(2) ?
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 ?
N2 C13 C9 . . 124.4(2) ?
N2 C13 H13 . . 117.8 ?
C9 C13 H13 . . 117.8 ?
C3 C14 H14A . . 109.5 ?
C3 C14 H14B . . 109.5 ?
H14A C14 H14B . . 109.5 ?
C3 C14 H14C . . 109.5 ?
H14A C14 H14C . . 109.5 ?
H14B C14 H14C . . 109.5 ?
C23 C15 C16 . . 119.9(2) ?
C23 C15 H15 . . 120.0 ?
C16 C15 H15 . . 120.0 ?
C15 C16 C17 . . 120.9(2) ?
C15 C16 H16 . . 119.6 ?
C17 C16 H16 . . 119.6 ?
C16 C17 C18 . . 118.1(2) ?
C16 C17 C28 . . 121.0(2) ?
C18 C17 C28 . . 120.82(19) ?
C24 C18 C17 . . 121.90(19) ?
C24 C18 N3 . . 121.30(19) ?
C17 C18 N3 . . 116.76(18) ?
N3 C19 C20 . . 122.8(2) ?
N3 C19 H19 . . 118.6 ?
C20 C19 H19 . . 118.6 ?
N4 C20 C27 . . 122.49(19) ?
N4 C20 C19 . . 114.61(18) ?
C27 C20 C19 . . 122.9(2) ?
N4 C21 C22 . . 124.2(2) ?
N4 C21 H21 . . 117.9 ?
C22 C21 H21 . . 117.9 ?
C26 C22 C21 . . 118.3(2) ?
C26 C22 H22 . . 120.9 ?
C21 C22 H22 . . 120.9 ?
C15 C23 C24 . . 121.8(2) ?
C15 C23 H23 . . 119.1 ?
C24 C23 H23 . . 119.1 ?
C23 C24 C18 . . 117.4(2) ?
C23 C24 C25 . . 120.6(2) ?
C18 C24 C25 . . 122.0(2) ?
C24 C25 H25A . . 109.5 ?
C24 C25 H25B . . 109.5 ?
H25A C25 H25B . . 109.5 ?
C24 C25 H25C . . 109.5 ?
H25A C25 H25C . . 109.5 ?
H25B C25 H25C . . 109.5 ?
C22 C26 C27 . . 118.8(2) ?
C22 C26 H26 . . 120.6 ?
C27 C26 H26 . . 120.6 ?
C26 C27 C20 . . 119.5(2) ?
C26 C27 H27 . . 120.3 ?
C20 C27 H27 . . 120.3 ?
C17 C28 H28A . . 109.5 ?
C17 C28 H28B . . 109.5 ?
H28A C28 H28B . . 109.5 ?
C17 C28 H28C . . 109.5 ?
H28A C28 H28C . . 109.5 ?
H28B C28 H28C . . 109.5 ?

_database_code_depnum_ccdc_archive 'CCDC 985732'
#######################################################################
#
#                 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        
2,6-Diisopropyl-N-(2-pyridinylmethylene)phenylamine
_chemical_name_common            ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C18 H22 N2'
_chemical_formula_iupac          ?
_chemical_formula_weight         266.38
_chemical_absolute_configuration ?

_chemical_melting_point          ?

_space_group_crystal_system      tetragonal
_space_group_name_H-M_alt        'P -4 21 c'
_space_group_name_Hall           'P -4 2n'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'y, -x, -z'
'-y, x, -z'
'x+1/2, -y+1/2, -z+1/2'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, z'
'-y+1/2, -x+1/2, z+1/2'
'y+1/2, x+1/2, z+1/2'

_cell_length_a                   15.3674(11)
_cell_length_b                   15.3674(11)
_cell_length_c                   13.9783(11)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     3301.1(4)
_cell_formula_units_Z            8
_cell_measurement_reflns_used    6058
_cell_measurement_theta_min      2.91
_cell_measurement_theta_max      21.47
_cell_measurement_temperature    200.(2)

_exptl_crystal_description       cubic
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.40
_exptl_crystal_size_mid          0.32
_exptl_crystal_size_min          0.29
_exptl_crystal_density_diffrn    1.072
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1152

_exptl_absorpt_coefficient_mu    0.063
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS V2008/1 (Bruker AXS)'
_exptl_absorpt_correction_T_min  0.98
_exptl_absorpt_correction_T_max  0.98

_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 8.3330

_diffrn_reflns_number            34152
_diffrn_reflns_av_R_equivalents  0.0657
_diffrn_reflns_av_sigmaI/netI    0.0227
_diffrn_reflns_theta_min         2.65
_diffrn_reflns_theta_max         24.28
_diffrn_reflns_theta_full        24.28
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measured_fraction_theta_full 0.999
_diffrn_reflns_limit_h_min       -17
_diffrn_reflns_limit_h_max       17
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_limit_l_max       14

_refine_special_details          
;
Refinement of F² against ALL reflections.  The weighted R-factor wR and
goodness of fit S are based on F², conventional R-factors R are based
on F, with F set to zero for negative F². The threshold expression of
F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is
not relevant to the choice of reflections for refinement.  R-factors based
on F² 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             1507
_reflns_number_gt                1323
_reflns_threshold_expression     >2sigma(I)

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_R_factor_all          0.0434
_refine_ls_R_factor_gt           0.0348
_refine_ls_wR_factor_gt          0.0851
_refine_ls_wR_factor_ref         0.0916
_refine_ls_goodness_of_fit_ref   1.012
_refine_ls_restrained_S_all      1.012
_refine_ls_number_reflns         1507
_refine_ls_number_parameters     186
_refine_ls_number_restraints     0
_refine_ls_hydrogen_treatment    constr
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0525P)²+0.5536P] where P=(Fo²+2Fc²)/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         0.134
_refine_diff_density_min         -0.109
_refine_ls_extinction_method     SHELXL
_refine_ls_extinction_coef       0.0021(4)
_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'

_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
N N2 0.37030(10) 0.83990(11) 0.75593(13) 0.0332(4) Uani d . 1 . .
N N1 0.38820(12) 1.06718(13) 0.7881(2) 0.0576(7) Uani d . 1 . .
C C1 0.4205(3) 0.6957(2) 0.5119(2) 0.0792(10) Uani d . 1 . .
H H1A 0.3734 0.6587 0.5361 0.119 Uiso calc R 1 . .
H H1B 0.4723 0.66 0.5003 0.119 Uiso calc R 1 . .
H H1C 0.4022 0.7232 0.452 0.119 Uiso calc R 1 . .
C C2 0.44157(19) 0.76524(18) 0.58509(19) 0.0502(7) Uani d . 1 . .
H H2 0.389 0.8031 0.5915 0.06 Uiso calc R 1 . .
C C3 0.46129(15) 0.72851(16) 0.68315(18) 0.0390(6) Uani d . 1 . .
C C4 0.42875(13) 0.76782(13) 0.76605(17) 0.0320(5) Uani d . 1 . .
C C5 0.39846(13) 0.91487(14) 0.77410(19) 0.0367(5) Uani d . 1 . .
H H5 0.4581 0.921 0.7906 0.044 Uiso calc R 1 . .
C C6 0.34427(13) 0.99351(14) 0.77119(16) 0.0336(5) Uani d . 1 . .
C C7 0.25619(14) 0.99287(16) 0.75452(18) 0.0397(5) Uani d . 1 . .
H H7 0.2262 0.9397 0.7441 0.048 Uiso calc R 1 . .
C C8 0.21248(15) 1.07089(16) 0.7533(2) 0.0547(8) Uani d . 1 . .
H H8 0.1516 1.0723 0.7414 0.066 Uiso calc R 1 . .
C C9 0.25695(15) 1.14636(16) 0.7692(2) 0.0539(7) Uani d . 1 . .
H H9 0.2278 1.2009 0.7681 0.065 Uiso calc R 1 . .
C C10 0.34371(16) 1.14180(16) 0.7865(3) 0.0608(8) Uani d . 1 . .
H H10 0.3744 1.1944 0.798 0.073 Uiso calc R 1 . .
C C11 0.5160(3) 0.8226(2) 0.5508(3) 0.0849(11) Uani d . 1 . .
H H11A 0.569 0.7876 0.545 0.127 Uiso calc R 1 . .
H H11B 0.5256 0.8696 0.597 0.127 Uiso calc R 1 . .
H H11C 0.5012 0.8476 0.4884 0.127 Uiso calc R 1 . .
C C12 0.51503(16) 0.65565(16) 0.6942(2) 0.0485(7) Uani d . 1 . .
H H12 0.5397 0.6288 0.6394 0.058 Uiso calc R 1 . .
C C13 0.53265(15) 0.62246(15) 0.7835(2) 0.0509(7) Uani d . 1 . .
H H13 0.5687 0.5725 0.7897 0.061 Uiso calc R 1 . .
C C14 0.49869(16) 0.66079(16) 0.86339(19) 0.0449(6) Uani d . 1 . .
H H14 0.5113 0.6369 0.9245 0.054 Uiso calc R 1 . .
C C15 0.44588(14) 0.73442(15) 0.85685(18) 0.0368(6) Uani d . 1 . .
C C16 0.41096(17) 0.77565(17) 0.94754(18) 0.0447(6) Uani d . 1 . .
H H16 0.3646 0.8179 0.9285 0.054 Uiso calc R 1 . .
C C17 0.4828(2) 0.8271(2) 0.9989(2) 0.0681(9) Uani d . 1 . .
H H17A 0.5298 0.7875 1.0174 0.102 Uiso calc R 1 . .
H H17B 0.4587 0.8549 1.0562 0.102 Uiso calc R 1 . .
H H17C 0.5058 0.8719 0.9558 0.102 Uiso calc R 1 . .
C C18 0.3699(2) 0.7099(2) 1.0149(2) 0.0767(10) Uani d . 1 . .
H H18A 0.4137 0.6673 1.0346 0.115 Uiso calc R 1 . .
H H18B 0.3221 0.68 0.982 0.115 Uiso calc R 1 . .
H H18C 0.3472 0.74 1.0714 0.115 Uiso calc R 1 . .


_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
N2 C5 . 1.257(3) ?
N2 C4 . 1.433(3) ?
N1 C10 . 1.335(3) ?
N1 C6 . 1.339(3) ?
C1 C2 . 1.515(4) ?
C1 H1A . 0.98 ?
C1 H1B . 0.98 ?
C1 H1C . 0.98 ?
C2 C3 . 1.513(4) ?
C2 C11 . 1.521(4) ?
C2 H2 . 1.0 ?
C3 C4 . 1.399(3) ?
C3 C12 . 1.400(3) ?
C4 C15 . 1.394(3) ?
C5 C6 . 1.468(3) ?
C5 H5 . 0.95 ?
C6 C7 . 1.374(3) ?
C7 C8 . 1.374(3) ?
C7 H7 . 0.95 ?
C8 C9 . 1.364(3) ?
C8 H8 . 0.95 ?
C9 C10 . 1.357(3) ?
C9 H9 . 0.95 ?
C10 H10 . 0.95 ?
C11 H11A . 0.98 ?
C11 H11B . 0.98 ?
C11 H11C . 0.98 ?
C12 C13 . 1.375(4) ?
C12 H12 . 0.95 ?
C13 C14 . 1.366(4) ?
C13 H13 . 0.95 ?
C14 C15 . 1.395(3) ?
C14 H14 . 0.95 ?
C15 C16 . 1.515(3) ?
C16 C18 . 1.518(4) ?
C16 C17 . 1.536(4) ?
C16 H16 . 1.0 ?
C17 H17A . 0.98 ?
C17 H17B . 0.98 ?
C17 H17C . 0.98 ?
C18 H18A . 0.98 ?
C18 H18B . 0.98 ?
C18 H18C . 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
C5 N2 C4 . . 118.22(16) ?
C10 N1 C6 . . 117.71(19) ?
C2 C1 H1A . . 109.5 ?
C2 C1 H1B . . 109.5 ?
H1A C1 H1B . . 109.5 ?
C2 C1 H1C . . 109.5 ?
H1A C1 H1C . . 109.5 ?
H1B C1 H1C . . 109.5 ?
C3 C2 C1 . . 113.0(2) ?
C3 C2 C11 . . 110.6(2) ?
C1 C2 C11 . . 110.9(3) ?
C3 C2 H2 . . 107.4 ?
C1 C2 H2 . . 107.4 ?
C11 C2 H2 . . 107.4 ?
C4 C3 C12 . . 117.7(2) ?
C4 C3 C2 . . 121.2(2) ?
C12 C3 C2 . . 121.1(2) ?
C15 C4 C3 . . 121.84(19) ?
C15 C4 N2 . . 119.5(2) ?
C3 C4 N2 . . 118.4(2) ?
N2 C5 C6 . . 123.63(18) ?
N2 C5 H5 . . 118.2 ?
C6 C5 H5 . . 118.2 ?
N1 C6 C7 . . 122.2(2) ?
N1 C6 C5 . . 113.90(17) ?
C7 C6 C5 . . 123.9(2) ?
C6 C7 C8 . . 118.5(2) ?
C6 C7 H7 . . 120.7 ?
C8 C7 H7 . . 120.7 ?
C9 C8 C7 . . 119.6(2) ?
C9 C8 H8 . . 120.2 ?
C7 C8 H8 . . 120.2 ?
C10 C9 C8 . . 118.5(2) ?
C10 C9 H9 . . 120.7 ?
C8 C9 H9 . . 120.7 ?
N1 C10 C9 . . 123.4(2) ?
N1 C10 H10 . . 118.3 ?
C9 C10 H10 . . 118.3 ?
C2 C11 H11A . . 109.5 ?
C2 C11 H11B . . 109.5 ?
H11A C11 H11B . . 109.5 ?
C2 C11 H11C . . 109.5 ?
H11A C11 H11C . . 109.5 ?
H11B C11 H11C . . 109.5 ?
C13 C12 C3 . . 120.9(2) ?
C13 C12 H12 . . 119.6 ?
C3 C12 H12 . . 119.6 ?
C14 C13 C12 . . 120.4(2) ?
C14 C13 H13 . . 119.8 ?
C12 C13 H13 . . 119.8 ?
C13 C14 C15 . . 121.2(2) ?
C13 C14 H14 . . 119.4 ?
C15 C14 H14 . . 119.4 ?
C4 C15 C14 . . 117.9(2) ?
C4 C15 C16 . . 122.7(2) ?
C14 C15 C16 . . 119.4(2) ?
C15 C16 C18 . . 112.8(2) ?
C15 C16 C17 . . 110.6(2) ?
C18 C16 C17 . . 110.6(3) ?
C15 C16 H16 . . 107.5 ?
C18 C16 H16 . . 107.5 ?
C17 C16 H16 . . 107.5 ?
C16 C17 H17A . . 109.5 ?
C16 C17 H17B . . 109.5 ?
H17A C17 H17B . . 109.5 ?
C16 C17 H17C . . 109.5 ?
H17A C17 H17C . . 109.5 ?
H17B C17 H17C . . 109.5 ?
C16 C18 H18A . . 109.5 ?
C16 C18 H18B . . 109.5 ?
H18A C18 H18B . . 109.5 ?
C16 C18 H18C . . 109.5 ?
H18A C18 H18C . . 109.5 ?
H18B C18 H18C . . 109.5 ?

_database_code_depnum_ccdc_archive 'CCDC 985733'
#######################################################################
#
#                 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        
'2-(2,6-dimethylphenyl)imidazo[1,5-a]pyridin-2-ium hexafluorophosphate'
_chemical_name_common            ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C15 H15 F6 N2 P'
_chemical_formula_iupac          ?
_chemical_formula_weight         368.26

_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                   9.498(5)
_cell_length_b                   17.132(8)
_cell_length_c                   10.148(5)
_cell_angle_alpha                90
_cell_angle_beta                 107.178(15)
_cell_angle_gamma                90
_cell_volume                     1577.6(13)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    3805
_cell_measurement_theta_min      2.3748
_cell_measurement_theta_max      19.9870
_cell_measurement_temperature    200.(2)

_exptl_crystal_description       plate
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.42
_exptl_crystal_size_mid          0.26
_exptl_crystal_size_min          0.05
_exptl_crystal_density_diffrn    1.550
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             752

_exptl_absorpt_coefficient_mu    0.238
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS V2008/1 (Bruker AXS)'
_exptl_absorpt_correction_T_min  0.66
_exptl_absorpt_correction_T_max  0.99

_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 8.3330



_diffrn_reflns_number            5480
_diffrn_reflns_av_R_equivalents  0.1041
_diffrn_reflns_av_sigmaI/netI    0.0702
_diffrn_reflns_theta_min         2.38
_diffrn_reflns_theta_max         20.65
_diffrn_reflns_theta_full        20.65
_diffrn_measured_fraction_theta_max 0.989
_diffrn_measured_fraction_theta_full 0.989
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_l_min       -10
_diffrn_reflns_limit_l_max       9

_refine_special_details          
;
Refinement of F² against ALL reflections.  The weighted R-factor wR and
goodness of fit S are based on F², conventional R-factors R are based
on F, with F set to zero for negative F². The threshold expression of
F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is
not relevant to the choice of reflections for refinement.  R-factors based
on F² 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             800
_reflns_number_gt                584
_reflns_threshold_expression     >2sigma(I)

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_R_factor_all          0.0759
_refine_ls_R_factor_gt           0.0518
_refine_ls_wR_factor_gt          0.1166
_refine_ls_wR_factor_ref         0.1263
_refine_ls_goodness_of_fit_ref   1.063
_refine_ls_restrained_S_all      1.063
_refine_ls_number_reflns         800
_refine_ls_number_parameters     120
_refine_ls_number_restraints     0
_refine_ls_hydrogen_treatment    mixed
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0525P)²+1.6764P] where P=(Fo²+2Fc²)/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         0.250
_refine_diff_density_min         -0.242
_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 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
P P1 1.0 0.20648(12) 0.75 0.0439(7) Uani d S 1 . .
F F1 0.9107(4) 0.2067(2) 0.8568(3) 0.0988(15) Uani d . 1 . .
F F2 0.8941(3) 0.27133(18) 0.6615(4) 0.0762(12) Uani d . 1 . .
F F3 0.8928(4) 0.14166(19) 0.6637(3) 0.0817(12) Uani d . 1 . .
N N1 0.5 0.2041(3) 0.75 0.0278(14) Uani d S 1 . .
C C4 0.5420(6) 0.4622(3) 0.7025(5) 0.0451(15) Uani d . 1 . .
H H4 0.5695 0.5105 0.671 0.054 Uiso calc R 1 . .
C C2 0.5828(6) 0.3955(3) 0.6569(5) 0.0421(15) Uani d . 1 . .
C C3 0.5420(4) 0.3242(3) 0.7040(4) 0.0290(12) Uani d P 0.5 . .
N N2 0.5420(4) 0.3242(3) 0.7040(4) 0.0290(12) Uani d P 0.5 . .
C C1 0.5671(5) 0.2497(3) 0.6787(5) 0.0300(13) Uani d . 1 . .
C C5 0.5 0.1202(4) 0.75 0.0316(18) Uani d S 1 . .
C C6 0.4170(5) 0.0817(3) 0.6311(5) 0.0383(14) Uani d . 1 . .
C C7 0.4195(6) 0.0017(4) 0.6344(6) 0.0571(18) Uani d . 1 . .
H H7 0.3648 -0.0267 0.5556 0.068 Uiso calc R 1 . .
C C8 0.5 -0.0382(5) 0.75 0.058(2) Uani d S 1 . .
H H8 0.5 -0.0937 0.75 0.069 Uiso calc SR 1 . .
C C9 0.3288(6) 0.1247(3) 0.5062(5) 0.0517(16) Uani d . 1 . .
H H9A 0.2691 0.0876 0.4393 0.078 Uiso calc R 1 . .
H H9B 0.3953 0.1526 0.4648 0.078 Uiso calc R 1 . .
H H9C 0.264 0.1622 0.5325 0.078 Uiso calc R 1 . .
H H2 0.645(5) 0.393(2) 0.594(5) 0.046(15) Uiso d . 1 . .
H H1 0.621(5) 0.229(3) 0.622(5) 0.052(16) Uiso d . 1 . .


_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 . 1.561(3) ?
P1 F1 2_756 1.561(3) ?
P1 F3 . 1.584(3) ?
P1 F3 2_756 1.584(3) ?
P1 F2 2_756 1.587(3) ?
P1 F2 . 1.587(3) ?
N1 C1 2_656 1.347(6) ?
N1 C1 . 1.347(6) ?
N1 C5 . 1.437(8) ?
C4 C2 . 1.333(7) ?
C4 C4 2_656 1.423(10) ?
C4 H4 . 0.95 ?
C2 C3 . 1.406(6) ?
C2 H2 . 0.99(5) ?
C3 C1 . 1.337(6) ?
C3 N2 2_656 1.396(7) ?
C3 C3 2_656 1.396(7) ?
C1 H1 . 0.94(5) ?
C5 C6 2_656 1.396(6) ?
C5 C6 . 1.396(6) ?
C6 C7 . 1.371(7) ?
C6 C9 . 1.491(7) ?
C7 C8 . 1.378(7) ?
C7 H7 . 0.95 ?
C8 C7 2_656 1.378(7) ?
C8 H8 . 0.95 ?
C9 H9A . 0.98 ?
C9 H9B . 0.98 ?
C9 H9C . 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
F1 P1 F1 . 2_756 179.7(3) ?
F1 P1 F3 . . 89.6(2) ?
F1 P1 F3 2_756 . 90.6(2) ?
F1 P1 F3 . 2_756 90.6(2) ?
F1 P1 F3 2_756 2_756 89.6(2) ?
F3 P1 F3 . 2_756 91.0(3) ?
F1 P1 F2 . 2_756 89.37(19) ?
F1 P1 F2 2_756 2_756 90.4(2) ?
F3 P1 F2 . 2_756 178.99(19) ?
F3 P1 F2 2_756 2_756 88.93(18) ?
F1 P1 F2 . . 90.4(2) ?
F1 P1 F2 2_756 . 89.37(19) ?
F3 P1 F2 . . 88.93(18) ?
F3 P1 F2 2_756 . 179.00(19) ?
F2 P1 F2 2_756 . 91.2(3) ?
C1 N1 C1 2_656 . 109.0(6) ?
C1 N1 C5 2_656 . 125.5(3) ?
C1 N1 C5 . . 125.5(3) ?
C2 C4 C4 . 2_656 120.9(3) ?
C2 C4 H4 . . 119.5 ?
C4 C4 H4 2_656 . 119.5 ?
C4 C2 C3 . . 119.3(5) ?
C4 C2 H2 . . 123.(3) ?
C3 C2 H2 . . 117.(3) ?
C1 C3 N2 . 2_656 107.3(3) ?
C1 C3 C3 . 2_656 107.3(3) ?
N2 C3 C3 2_656 2_656 0.0(4) ?
C1 C3 C2 . . 132.9(4) ?
N2 C3 C2 2_656 . 119.8(3) ?
C3 C3 C2 2_656 . 119.8(3) ?
C3 C1 N1 . . 108.2(5) ?
C3 C1 H1 . . 129.(3) ?
N1 C1 H1 . . 122.(3) ?
C6 C5 C6 2_656 . 123.7(7) ?
C6 C5 N1 2_656 . 118.2(3) ?
C6 C5 N1 . . 118.2(3) ?
C7 C6 C5 . . 116.7(5) ?
C7 C6 C9 . . 121.1(5) ?
C5 C6 C9 . . 122.2(5) ?
C6 C7 C8 . . 121.2(6) ?
C6 C7 H7 . . 119.4 ?
C8 C7 H7 . . 119.4 ?
C7 C8 C7 . 2_656 120.5(8) ?
C7 C8 H8 . . 119.8 ?
C7 C8 H8 2_656 . 119.8 ?
C6 C9 H9A . . 109.5 ?
C6 C9 H9B . . 109.5 ?
H9A C9 H9B . . 109.5 ?
C6 C9 H9C . . 109.5 ?
H9A C9 H9C . . 109.5 ?
H9B C9 H9C . . 109.5 ?

# start Validation Reply Form
_vrf_PUBL006_GLOBAL              
;
PROBLEM: _publ_requested_journal is missing
RESPONSE: ...
;
_vrf_THETM01_I                   
;
PROBLEM: The value of sine(theta_max)/wavelength is less than 0.550
RESPONSE: The data were measured with the fully automated
diffractometer SMART X2S. With this instrument it is not possible to change
any parameters of the measurement strategy. Therefore, no reflections at
higher than the given theta angle could be measured.
;
_vrf_PLAT023_I                   
;
PROBLEM: Resolution (too) Low [sin(theta)/Lambda < 0.6]..      20.65 Deg. 
RESPONSE: The data were measured with the fully automated
diffractometer SMART X2S. With this instrument it is not possible to change
any parameters of the measurement strategy. Therefore, no reflections at
higher than the given theta angle could be measured.
;
# end Validation Reply Form

_database_code_depnum_ccdc_archive 'CCDC 985734'
#######################################################################
#
#                 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        
'2-(2,6-diisopropylphenyl)imidazo[1,5-a]pyridin-2-ium hexafluorophosphate'
_chemical_name_common            ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C19 H23 F6 N2 P'
_chemical_formula_iupac          ?
_chemical_formula_weight         424.36
_chemical_absolute_configuration ?

_chemical_melting_point          ?

_space_group_crystal_system      orthorhombic
_space_group_name_H-M_alt        'P n a 21'
_space_group_name_Hall           'P 2c -2n'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, z+1/2'
'-x+1/2, y+1/2, z+1/2'
'x+1/2, -y+1/2, z'

_cell_length_a                   16.3670(16)
_cell_length_b                   13.090(2)
_cell_length_c                   9.463(3)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     2027.4(7)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    9907
_cell_measurement_theta_min      2.4830
_cell_measurement_theta_max      20.9830
_cell_measurement_temperature    200.(2)

_exptl_crystal_description       plate
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.400
_exptl_crystal_size_mid          0.370
_exptl_crystal_size_min          0.130
_exptl_crystal_density_diffrn    1.390
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             880

_exptl_absorpt_coefficient_mu    0.196
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS V2012/1 (Bruker AXS Inc.)'
_exptl_absorpt_correction_T_min  0.82
_exptl_absorpt_correction_T_max  0.97

_exptl_special_details           
;
;

_diffrn_ambient_temperature      200.(2)

_diffrn_source                   ?
_diffrn_source_type              ?

_diffrn_radiation_type           ?
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_monochromator  ?

_diffrn_measurement_device_type  ?
_diffrn_measurement_method       ?

_diffrn_detector_area_resol_mean 8.3330

_diffrn_reflns_number            27566
_diffrn_reflns_av_R_equivalents  0.0714
_diffrn_reflns_av_sigmaI/netI    0.0308
_diffrn_reflns_theta_min         2.49
_diffrn_reflns_theta_max         21.80
_diffrn_reflns_theta_full        21.80
_diffrn_measured_fraction_theta_max 0.986
_diffrn_measured_fraction_theta_full 0.986
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_l_min       -9
_diffrn_reflns_limit_l_max       9

_refine_special_details          
;
Refinement of F² against ALL reflections.  The weighted R-factor wR and
goodness of fit S are based on F², conventional R-factors R are based
on F, with F set to zero for negative F². The threshold expression of
F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is
not relevant to the choice of reflections for refinement.  R-factors based
on F² 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             2382
_reflns_number_gt                2143
_reflns_threshold_expression     >2sigma(I)

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_R_factor_all          0.0624
_refine_ls_R_factor_gt           0.0553
_refine_ls_wR_factor_gt          0.1498
_refine_ls_wR_factor_ref         0.1576
_refine_ls_goodness_of_fit_ref   1.033
_refine_ls_restrained_S_all      1.032
_refine_ls_number_reflns         2382
_refine_ls_number_parameters     261
_refine_ls_number_restraints     5
_refine_ls_hydrogen_treatment    mixed
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.1082P)²+1.2494P] where P=(Fo²+2Fc²)/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         0.402
_refine_diff_density_min         -0.328
_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   0.1(2)

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 (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
C C8 0.25659(18) 0.8810(2) 0.8816(3) 0.0453(12) Uani d G 1 . .
C C13 0.22857(18) 0.7964(2) 0.8073(4) 0.0538(14) Uani d G 1 . .
C C12 0.2685(2) 0.7652(3) 0.6851(4) 0.0675(17) Uani d G 1 . .
H H12 0.2493 0.7073 0.6343 0.081 Uiso calc R 1 . .
C C11 0.3364(2) 0.8187(3) 0.6370(3) 0.0747(18) Uani d G 1 . .
H H11 0.3637 0.7973 0.5535 0.09 Uiso calc R 1 . .
C C10 0.36441(19) 0.9033(3) 0.7113(4) 0.0664(15) Uani d G 1 . .
H H10 0.4108 0.9399 0.6785 0.08 Uiso calc R 1 . .
C C9 0.32451(19) 0.9345(2) 0.8336(4) 0.0554(14) Uani d G 1 . .
P P1 0.06577(9) 0.20430(11) 0.74814(18) 0.0602(5) Uani d . 1 . .
F F3 0.0662(4) 0.3222(4) 0.7668(8) 0.157(2) Uani d . 1 . .
F F1 0.0270(3) 0.1906(4) 0.9000(4) 0.1134(16) Uani d . 1 . .
C C4 0.0869(3) 1.0596(4) 1.2285(7) 0.0624(15) Uani d D 1 . .
F F2 0.1532(3) 0.2132(4) 0.8236(5) 0.1178(16) Uani d . 1 . .
C C17 0.1520(3) 0.7375(4) 0.8599(7) 0.0643(16) Uani d . 1 . .
H H17 0.1346 0.7682 0.9519 0.077 Uiso calc R 1 . .
F F4 0.0813(3) 0.0842(3) 0.7358(5) 0.1095(15) Uani d . 1 . .
F F5 0.1106(4) 0.2245(4) 0.5998(5) 0.1260(19) Uani d . 1 . .
C C14 0.3587(3) 1.0274(4) 0.9127(7) 0.0620(15) Uani d . 1 . .
H H14 0.3253 1.0363 1.0003 0.074 Uiso calc R 1 . .
C C16 0.4467(4) 1.0102(6) 0.9589(8) 0.085(2) Uani d . 1 . .
H H16A 0.4664 1.0706 1.0098 0.127 Uiso calc R 1 . .
H H16B 0.481 0.9985 0.8755 0.127 Uiso calc R 1 . .
H H16C 0.4494 0.9505 1.0211 0.127 Uiso calc R 1 . .
C C1 0.2354(3) 0.8753(4) 1.1367(6) 0.0464(12) Uani d D 1 . .
N N2 0.2183(2) 0.9113(3) 1.0073(4) 0.0374(9) Uani d . 1 . .
C C2 0.1597(3) 0.9843(4) 1.0204(6) 0.0447(12) Uani d D 1 . .
C C5 0.0826(4) 1.0502(6) 1.3699(8) 0.0748(19) Uani d . 1 . .
H H5 0.0463 1.0929 1.4212 0.09 Uiso calc R 1 . .
C C6 0.1305(5) 0.9790(6) 1.4433(7) 0.082(2) Uani d . 1 . .
H H6 0.126 0.9753 1.5433 0.098 Uiso calc R 1 . .
C C7 0.1819(4) 0.9167(5) 1.3776(7) 0.0700(17) Uani d D 1 . .
C C15 0.3505(4) 1.1249(5) 0.8270(10) 0.095(2) Uani d . 1 . .
H H15A 0.3766 1.1813 0.8778 0.143 Uiso calc R 1 . .
H H15B 0.2925 1.1404 0.8128 0.143 Uiso calc R 1 . .
H H15C 0.3771 1.1158 0.7351 0.143 Uiso calc R 1 . .
C C19 0.0815(4) 0.7493(7) 0.7549(12) 0.114(3) Uani d . 1 . .
H H19A 0.071 0.822 0.7384 0.172 Uiso calc R 1 . .
H H19B 0.0323 0.7171 0.7937 0.172 Uiso calc R 1 . .
H H19C 0.096 0.7162 0.6655 0.172 Uiso calc R 1 . .
C C18 0.1704(5) 0.6252(5) 0.8849(12) 0.111(3) Uani d . 1 . .
H H18A 0.1757 0.5902 0.7938 0.166 Uiso calc R 1 . .
H H18B 0.1258 0.5943 0.9392 0.166 Uiso calc R 1 . .
H H18C 0.2216 0.6187 0.9378 0.166 Uiso calc R 1 . .
F F6 -0.0179(3) 0.1925(4) 0.6724(5) 0.1100(14) Uani d . 1 . .
N N1A 0.1411(3) 0.9936(3) 1.1564(5) 0.0456(11) Uani d P 0.5 . .
C C3A 0.1411(3) 0.9936(3) 1.1564(5) 0.0456(11) Uani d P 0.5 . .
N N1B 0.1891(3) 0.9235(3) 1.2288(5) 0.0440(11) Uani d P 0.5 . .
C C3B 0.1891(3) 0.9235(3) 1.2288(5) 0.0440(11) Uani d P 0.5 . .
H H1 0.273(2) 0.824(3) 1.163(5) 0.053(14) Uiso d D 1 . .
H H4 0.050(2) 1.094(3) 1.169(4) 0.042(14) Uiso d D 1 . .
H H7 0.214(3) 0.866(3) 1.423(6) 0.067(17) Uiso d D 1 . .
H H2 0.136(2) 1.024(3) 0.947(3) 0.028(11) Uiso d D 1 . .


_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
C8 C13 . 1.39 ?
C8 C9 . 1.39 ?
C8 N2 . 1.401(4) ?
C13 C12 . 1.39 ?
C13 C17 . 1.553(6) ?
C12 C11 . 1.39 ?
C12 H12 . 0.95 ?
C11 C10 . 1.39 ?
C11 H11 . 0.95 ?
C10 C9 . 1.39 ?
C10 H10 . 0.95 ?
C9 C14 . 1.534(6) ?
P1 F3 . 1.553(5) ?
P1 F6 . 1.554(4) ?
P1 F1 . 1.582(4) ?
P1 F4 . 1.597(4) ?
P1 F2 . 1.604(5) ?
P1 F5 . 1.605(5) ?
C4 C5 . 1.345(10) ?
C4 N1A . 1.413(7) ?
C4 H4 . 0.942(10) ?
C17 C18 . 1.519(9) ?
C17 C19 . 1.531(9) ?
C17 H17 . 1.0 ?
C14 C15 . 1.517(9) ?
C14 C16 . 1.523(8) ?
C14 H14 . 1.0 ?
C16 H16A . 0.98 ?
C16 H16B . 0.98 ?
C16 H16C . 0.98 ?
C1 N1B . 1.315(7) ?
C1 N2 . 1.341(6) ?
C1 H1 . 0.946(10) ?
N2 C2 . 1.360(6) ?
C2 N1A . 1.328(7) ?
C2 H2 . 0.946(10) ?
C5 C6 . 1.402(11) ?
C5 H5 . 0.95 ?
C6 C7 . 1.326(10) ?
C6 H6 . 0.95 ?
C7 N1B . 1.416(8) ?
C7 H7 . 0.947(10) ?
C15 H15A . 0.98 ?
C15 H15B . 0.98 ?
C15 H15C . 0.98 ?
C19 H19A . 0.98 ?
C19 H19B . 0.98 ?
C19 H19C . 0.98 ?
C18 H18A . 0.98 ?
C18 H18B . 0.98 ?
C18 H18C . 0.98 ?
N1A N1B . 1.389(6) ?

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
C13 C8 C9 . . 120.0 ?
C13 C8 N2 . . 120.4(2) ?
C9 C8 N2 . . 119.5(2) ?
C12 C13 C8 . . 120.0 ?
C12 C13 C17 . . 120.0(3) ?
C8 C13 C17 . . 120.0(3) ?
C13 C12 C11 . . 120.0 ?
C13 C12 H12 . . 120.0 ?
C11 C12 H12 . . 120.0 ?
C12 C11 C10 . . 120.0 ?
C12 C11 H11 . . 120.0 ?
C10 C11 H11 . . 120.0 ?
C11 C10 C9 . . 120.0 ?
C11 C10 H10 . . 120.0 ?
C9 C10 H10 . . 120.0 ?
C10 C9 C8 . . 120.0 ?
C10 C9 C14 . . 117.9(3) ?
C8 C9 C14 . . 122.1(3) ?
F3 P1 F6 . . 98.9(3) ?
F3 P1 F1 . . 90.6(3) ?
F6 P1 F1 . . 93.1(3) ?
F3 P1 F4 . . 170.3(3) ?
F6 P1 F4 . . 90.5(3) ?
F1 P1 F4 . . 91.1(3) ?
F3 P1 F2 . . 82.7(3) ?
F6 P1 F2 . . 178.1(3) ?
F1 P1 F2 . . 87.8(3) ?
F4 P1 F2 . . 87.8(3) ?
F3 P1 F5 . . 86.2(3) ?
F6 P1 F5 . . 90.9(3) ?
F1 P1 F5 . . 175.2(2) ?
F4 P1 F5 . . 91.4(3) ?
F2 P1 F5 . . 88.3(3) ?
C5 C4 N1A . . 117.2(6) ?
C5 C4 H4 . . 127.(3) ?
N1A C4 H4 . . 114.(3) ?
C18 C17 C19 . . 110.4(6) ?
C18 C17 C13 . . 111.7(4) ?
C19 C17 C13 . . 110.5(5) ?
C18 C17 H17 . . 108.0 ?
C19 C17 H17 . . 108.0 ?
C13 C17 H17 . . 108.0 ?
C15 C14 C16 . . 111.2(5) ?
C15 C14 C9 . . 111.9(5) ?
C16 C14 C9 . . 111.6(5) ?
C15 C14 H14 . . 107.3 ?
C16 C14 H14 . . 107.3 ?
C9 C14 H14 . . 107.3 ?
C14 C16 H16A . . 109.5 ?
C14 C16 H16B . . 109.5 ?
H16A C16 H16B . . 109.5 ?
C14 C16 H16C . . 109.5 ?
H16A C16 H16C . . 109.5 ?
H16B C16 H16C . . 109.5 ?
N1B C1 N2 . . 108.5(4) ?
N1B C1 H1 . . 123.(3) ?
N2 C1 H1 . . 129.(3) ?
C1 N2 C2 . . 108.1(4) ?
C1 N2 C8 . . 125.6(3) ?
C2 N2 C8 . . 126.3(4) ?
N1A C2 N2 . . 108.4(4) ?
N1A C2 H2 . . 124.(2) ?
N2 C2 H2 . . 127.(3) ?
C4 C5 C6 . . 121.6(6) ?
C4 C5 H5 . . 119.2 ?
C6 C5 H5 . . 119.2 ?
C7 C6 C5 . . 122.0(6) ?
C7 C6 H6 . . 119.0 ?
C5 C6 H6 . . 119.0 ?
C6 C7 N1B . . 118.7(7) ?
C6 C7 H7 . . 124.(4) ?
N1B C7 H7 . . 117.(4) ?
C14 C15 H15A . . 109.5 ?
C14 C15 H15B . . 109.5 ?
H15A C15 H15B . . 109.5 ?
C14 C15 H15C . . 109.5 ?
H15A C15 H15C . . 109.5 ?
H15B C15 H15C . . 109.5 ?
C17 C19 H19A . . 109.5 ?
C17 C19 H19B . . 109.5 ?
H19A C19 H19B . . 109.5 ?
C17 C19 H19C . . 109.5 ?
H19A C19 H19C . . 109.5 ?
H19B C19 H19C . . 109.5 ?
C17 C18 H18A . . 109.5 ?
C17 C18 H18B . . 109.5 ?
H18A C18 H18B . . 109.5 ?
C17 C18 H18C . . 109.5 ?
H18A C18 H18C . . 109.5 ?
H18B C18 H18C . . 109.5 ?
C2 N1A N1B . . 106.7(4) ?
C2 N1A C4 . . 131.9(5) ?
N1B N1A C4 . . 121.3(5) ?
C1 N1B N1A . . 108.4(4) ?
C1 N1B C7 . . 132.6(5) ?
N1A N1B C7 . . 119.0(5) ?

# start Validation Reply Form
_vrf_PLAT023_I                   
;
PROBLEM: Resolution (too) Low [sin(theta)/Lambda < 0.6]..      21.80 Degree
RESPONSE: The data were measured with the fully automated
diffractometer SMART X2S. With this instrument it is not possible to change
any parameters of the measurement strategy. Therefore, no reflections at
higher than the given theta angle could be measured.
;
# end Validation Reply Form

_database_code_depnum_ccdc_archive 'CCDC 985735'
#######################################################################
#
#                 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        
Chlorido-{2-(2,6-diisopropylphenyl)imidazo[1,5-a]pyridin-3-ylidene}silver(I)
_chemical_name_common            ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C38 H44 Ag F6 N4 P'
_chemical_formula_iupac          ?
_chemical_formula_weight         809.61

_chemical_melting_point          ?

_space_group_crystal_system      triclinic
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   8.527(2)
_cell_length_b                   10.424(3)
_cell_length_c                   11.059(3)
_cell_angle_alpha                84.065(8)
_cell_angle_beta                 73.767(8)
_cell_angle_gamma                80.064(9)
_cell_volume                     928.1(4)
_cell_formula_units_Z            1
_cell_measurement_reflns_used    3040
_cell_measurement_theta_min      2.51
_cell_measurement_theta_max      22.48
_cell_measurement_temperature    200.(2)

_exptl_crystal_description       needle
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.37
_exptl_crystal_size_mid          0.16
_exptl_crystal_size_min          0.14
_exptl_crystal_density_diffrn    1.449
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             416

_exptl_absorpt_coefficient_mu    0.649
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS V2008/1 (Bruker AXS)'
_exptl_absorpt_correction_T_min  0.80
_exptl_absorpt_correction_T_max  0.91

_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 8.3330

_diffrn_reflns_number            17396
_diffrn_reflns_av_R_equivalents  0.1344
_diffrn_reflns_av_sigmaI/netI    0.0960
_diffrn_reflns_theta_min         1.92
_diffrn_reflns_theta_max         25.07
_diffrn_reflns_theta_full        25.07
_diffrn_measured_fraction_theta_max 0.987
_diffrn_measured_fraction_theta_full 0.987
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_limit_l_max       13

_refine_special_details          
;
Refinement of F² against ALL reflections.  The weighted R-factor wR and
goodness of fit S are based on F², conventional R-factors R are based
on F, with F set to zero for negative F². The threshold expression of
F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is
not relevant to the choice of reflections for refinement.  R-factors based
on F² 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             3254
_reflns_number_gt                2657
_reflns_threshold_expression     >2sigma(I)

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_R_factor_all          0.0689
_refine_ls_R_factor_gt           0.0537
_refine_ls_wR_factor_gt          0.1100
_refine_ls_wR_factor_ref         0.1300
_refine_ls_goodness_of_fit_ref   1.028
_refine_ls_restrained_S_all      1.028
_refine_ls_number_reflns         3254
_refine_ls_number_parameters     233
_refine_ls_number_restraints     0
_refine_ls_hydrogen_treatment    constr
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0582P)²+0.0000P] where P=(Fo²+2Fc²)/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         0.774
_refine_diff_density_min         -0.748
_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'
Ag Ag -0.8971 1.1015 '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
Ag Ag1 0 0 1.0 0.0310(2) Uani d S 1 . .
P P1 0.5 0.5 0.5 0.0396(5) Uani d S 1 . .
F F1 0.4645(6) 0.4961(5) 0.3695(4) 0.1058(16) Uani d . 1 . .
F F2 0.4612(5) 0.3552(3) 0.5338(3) 0.0775(12) Uani d . 1 . .
F F3 0.6852(4) 0.4493(4) 0.4363(4) 0.1030(16) Uani d . 1 . .
N N1 0.1210(5) 0.2686(4) 1.0082(3) 0.0334(10) Uani d . 1 . .
N N2 0.2252(4) 0.1789(3) 0.8331(3) 0.0242(8) Uani d . 1 . .
C C1 0.1148(5) 0.1637(4) 0.9465(4) 0.0277(10) Uani d . 1 . .
C C2 0.2325(6) 0.3468(5) 0.9344(5) 0.0374(12) Uani d . 1 . .
C C3 0.2518(8) 0.4607(5) 0.9852(6) 0.0561(16) Uani d . 1 . .
H H3 0.3255 0.5173 0.937 0.067 Uiso calc R 1 . .
C C4 0.1611(10) 0.4868(6) 1.1058(7) 0.072(2) Uani d . 1 . .
H H4 0.174 0.562 1.1415 0.087 Uiso calc R 1 . .
C C5 0.0500(9) 0.4059(6) 1.1778(6) 0.064(2) Uani d . 1 . .
H H5 -0.0122 0.4279 1.2606 0.077 Uiso calc R 1 . .
C C6 0.0305(7) 0.2987(6) 1.1316(5) 0.0512(16) Uani d . 1 . .
H H6 -0.0435 0.2431 1.1814 0.061 Uiso calc R 1 . .
C C7 0.2968(6) 0.2887(4) 0.8229(4) 0.0330(11) Uani d . 1 . .
H H7 0.3763 0.3186 0.7516 0.04 Uiso calc R 1 . .
C C8 0.2566(5) 0.0862(4) 0.7373(4) 0.0238(10) Uani d . 1 . .
C C9 0.1782(5) 0.1167(4) 0.6407(4) 0.0276(10) Uani d . 1 . .
C C10 0.0612(6) 0.2440(5) 0.6327(4) 0.0337(11) Uani d . 1 . .
H H10 0.0877 0.3096 0.681 0.04 Uiso calc R 1 . .
C C11 0.0771(7) 0.2990(5) 0.4991(5) 0.0524(15) Uani d . 1 . .
H H11A 0.0437 0.2387 0.452 0.079 Uiso calc R 1 . .
H H11B 0.1921 0.3105 0.4589 0.079 Uiso calc R 1 . .
H H11C 0.0057 0.3835 0.4996 0.079 Uiso calc R 1 . .
C C12 -0.1161(6) 0.2212(5) 0.6936(5) 0.0468(14) Uani d . 1 . .
H H12A -0.1912 0.3029 0.6887 0.07 Uiso calc R 1 . .
H H12B -0.1282 0.1912 0.7822 0.07 Uiso calc R 1 . .
H H12C -0.1429 0.1549 0.6491 0.07 Uiso calc R 1 . .
C C13 0.2024(6) 0.0217(5) 0.5552(4) 0.0382(12) Uani d . 1 . .
H H13 0.1493 0.0385 0.489 0.046 Uiso calc R 1 . .
C C14 0.3017(6) -0.0962(5) 0.5642(5) 0.0450(14) Uani d . 1 . .
H H14 0.3163 -0.1597 0.5047 0.054 Uiso calc R 1 . .
C C15 0.3795(6) -0.1220(5) 0.6592(4) 0.0381(12) Uani d . 1 . .
H H15 0.4491 -0.203 0.6637 0.046 Uiso calc R 1 . .
C C16 0.3581(5) -0.0316(4) 0.7491(4) 0.0288(11) Uani d . 1 . .
C C17 0.4481(6) -0.0619(5) 0.8510(4) 0.0350(12) Uani d . 1 . .
H H17 0.4016 0.0064 0.914 0.042 Uiso calc R 1 . .
C C18 0.6299(6) -0.0539(7) 0.7971(5) 0.0603(17) Uani d . 1 . .
H H18A 0.6784 -0.1184 0.7332 0.09 Uiso calc R 1 . .
H H18B 0.6856 -0.072 0.8648 0.09 Uiso calc R 1 . .
H H18C 0.6436 0.0337 0.7582 0.09 Uiso calc R 1 . .
C C19 0.4233(7) -0.1940(5) 0.9209(5) 0.0534(16) Uani d . 1 . .
H H19A 0.3049 -0.198 0.9538 0.08 Uiso calc R 1 . .
H H19B 0.4747 -0.2053 0.991 0.08 Uiso calc R 1 . .
H H19C 0.4746 -0.2636 0.8628 0.08 Uiso calc R 1 . .


_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
Ag1 C1 2_557 2.065(5) ?
Ag1 C1 . 2.065(5) ?
P1 F3 2_666 1.560(3) ?
P1 F3 . 1.560(3) ?
P1 F1 . 1.560(4) ?
P1 F1 2_666 1.561(4) ?
P1 F2 . 1.586(3) ?
P1 F2 2_666 1.586(3) ?
N1 C1 . 1.363(6) ?
N1 C2 . 1.389(6) ?
N1 C6 . 1.405(6) ?
N2 C1 . 1.355(5) ?
N2 C7 . 1.368(6) ?
N2 C8 . 1.446(5) ?
C2 C7 . 1.360(7) ?
C2 C3 . 1.418(7) ?
C3 C4 . 1.370(9) ?
C3 H3 . 0.95 ?
C4 C5 . 1.399(10) ?
C4 H4 . 0.95 ?
C5 C6 . 1.330(9) ?
C5 H5 . 0.95 ?
C6 H6 . 0.95 ?
C7 H7 . 0.95 ?
C8 C16 . 1.392(6) ?
C8 C9 . 1.394(6) ?
C9 C13 . 1.390(6) ?
C9 C10 . 1.528(6) ?
C10 C11 . 1.506(7) ?
C10 C12 . 1.522(7) ?
C10 H10 . 1.0 ?
C11 H11A . 0.98 ?
C11 H11B . 0.98 ?
C11 H11C . 0.98 ?
C12 H12A . 0.98 ?
C12 H12B . 0.98 ?
C12 H12C . 0.98 ?
C13 C14 . 1.378(7) ?
C13 H13 . 0.95 ?
C14 C15 . 1.373(7) ?
C14 H14 . 0.95 ?
C15 C16 . 1.394(6) ?
C15 H15 . 0.95 ?
C16 C17 . 1.512(6) ?
C17 C18 . 1.511(7) ?
C17 C19 . 1.526(7) ?
C17 H17 . 1.0 ?
C18 H18A . 0.98 ?
C18 H18B . 0.98 ?
C18 H18C . 0.98 ?
C19 H19A . 0.98 ?
C19 H19B . 0.98 ?
C19 H19C . 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 Ag1 C1 2_557 . 180.0000(10) ?
F3 P1 F3 2_666 . 179.9990(10) ?
F3 P1 F1 2_666 . 91.9(3) ?
F3 P1 F1 . . 88.1(3) ?
F3 P1 F1 2_666 2_666 88.1(3) ?
F3 P1 F1 . 2_666 91.9(3) ?
F1 P1 F1 . 2_666 179.9990(10) ?
F3 P1 F2 2_666 . 88.8(2) ?
F3 P1 F2 . . 91.2(2) ?
F1 P1 F2 . . 89.3(2) ?
F1 P1 F2 2_666 . 90.7(2) ?
F3 P1 F2 2_666 2_666 91.2(2) ?
F3 P1 F2 . 2_666 88.8(2) ?
F1 P1 F2 . 2_666 90.7(2) ?
F1 P1 F2 2_666 2_666 89.3(2) ?
F2 P1 F2 . 2_666 179.9990(10) ?
C1 N1 C2 . . 111.9(4) ?
C1 N1 C6 . . 126.5(5) ?
C2 N1 C6 . . 121.6(5) ?
C1 N2 C7 . . 112.4(4) ?
C1 N2 C8 . . 121.1(4) ?
C7 N2 C8 . . 126.5(3) ?
N2 C1 N1 . . 103.2(4) ?
N2 C1 Ag1 . . 122.6(3) ?
N1 C1 Ag1 . . 133.7(3) ?
C7 C2 N1 . . 105.5(4) ?
C7 C2 C3 . . 135.9(5) ?
N1 C2 C3 . . 118.6(5) ?
C4 C3 C2 . . 118.1(6) ?
C4 C3 H3 . . 121.0 ?
C2 C3 H3 . . 121.0 ?
C3 C4 C5 . . 122.0(6) ?
C3 C4 H4 . . 119.0 ?
C5 C4 H4 . . 119.0 ?
C6 C5 C4 . . 120.7(6) ?
C6 C5 H5 . . 119.6 ?
C4 C5 H5 . . 119.6 ?
C5 C6 N1 . . 119.0(6) ?
C5 C6 H6 . . 120.5 ?
N1 C6 H6 . . 120.5 ?
C2 C7 N2 . . 106.9(4) ?
C2 C7 H7 . . 126.5 ?
N2 C7 H7 . . 126.5 ?
C16 C8 C9 . . 123.2(4) ?
C16 C8 N2 . . 118.3(4) ?
C9 C8 N2 . . 118.5(4) ?
C13 C9 C8 . . 116.9(4) ?
C13 C9 C10 . . 120.6(4) ?
C8 C9 C10 . . 122.4(4) ?
C11 C10 C12 . . 109.5(4) ?
C11 C10 C9 . . 112.8(4) ?
C12 C10 C9 . . 109.4(4) ?
C11 C10 H10 . . 108.4 ?
C12 C10 H10 . . 108.4 ?
C9 C10 H10 . . 108.4 ?
C10 C11 H11A . . 109.5 ?
C10 C11 H11B . . 109.5 ?
H11A C11 H11B . . 109.5 ?
C10 C11 H11C . . 109.5 ?
H11A C11 H11C . . 109.5 ?
H11B C11 H11C . . 109.5 ?
C10 C12 H12A . . 109.5 ?
C10 C12 H12B . . 109.5 ?
H12A C12 H12B . . 109.5 ?
C10 C12 H12C . . 109.5 ?
H12A C12 H12C . . 109.5 ?
H12B C12 H12C . . 109.5 ?
C14 C13 C9 . . 121.5(5) ?
C14 C13 H13 . . 119.3 ?
C9 C13 H13 . . 119.3 ?
C15 C14 C13 . . 120.0(5) ?
C15 C14 H14 . . 120.0 ?
C13 C14 H14 . . 120.0 ?
C14 C15 C16 . . 121.2(4) ?
C14 C15 H15 . . 119.4 ?
C16 C15 H15 . . 119.4 ?
C8 C16 C15 . . 117.1(4) ?
C8 C16 C17 . . 122.9(4) ?
C15 C16 C17 . . 119.9(4) ?
C18 C17 C16 . . 110.7(4) ?
C18 C17 C19 . . 110.6(4) ?
C16 C17 C19 . . 112.6(4) ?
C18 C17 H17 . . 107.6 ?
C16 C17 H17 . . 107.6 ?
C19 C17 H17 . . 107.6 ?
C17 C18 H18A . . 109.5 ?
C17 C18 H18B . . 109.5 ?
H18A C18 H18B . . 109.5 ?
C17 C18 H18C . . 109.5 ?
H18A C18 H18C . . 109.5 ?
H18B C18 H18C . . 109.5 ?
C17 C19 H19A . . 109.5 ?
C17 C19 H19B . . 109.5 ?
H19A C19 H19B . . 109.5 ?
C17 C19 H19C . . 109.5 ?
H19A C19 H19C . . 109.5 ?
H19B C19 H19C . . 109.5 ?

_database_code_depnum_ccdc_archive 'CCDC 985736'
#######################################################################
#
#                 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        
Bromido-{2-(2,6-dimethylphenyl)imidazo[1,5-a]pyridin-3-ylidene}gold(I)
_chemical_name_common            ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C15 H14 Au Br N2'
_chemical_formula_iupac          ?
_chemical_formula_weight         499.16

_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                   10.646(2)
_cell_length_b                   10.8148(19)
_cell_length_c                   13.179(3)
_cell_angle_alpha                90
_cell_angle_beta                 107.979(7)
_cell_angle_gamma                90
_cell_volume                     1443.3(5)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    3266
_cell_measurement_theta_min      2.75
_cell_measurement_theta_max      24.93
_cell_measurement_temperature    200.(2)

_exptl_crystal_description       plate
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.57
_exptl_crystal_size_mid          0.17
_exptl_crystal_size_min          0.08
_exptl_crystal_density_diffrn    2.297
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             928

_exptl_absorpt_coefficient_mu    12.949
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS V2008/1 (Bruker AXS)'
_exptl_absorpt_correction_T_min  0.05
_exptl_absorpt_correction_T_max  0.42

_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 8.3330

_diffrn_reflns_number            8914
_diffrn_reflns_av_R_equivalents  0.0646
_diffrn_reflns_av_sigmaI/netI    0.0624
_diffrn_reflns_theta_min         2.49
_diffrn_reflns_theta_max         25.01
_diffrn_reflns_theta_full        25.01
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measured_fraction_theta_full 0.997
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_limit_l_max       15

_refine_special_details          
;
Refinement of F² against ALL reflections.  The weighted R-factor wR and
goodness of fit S are based on F², conventional R-factors R are based
on F, with F set to zero for negative F². The threshold expression of
F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is
not relevant to the choice of reflections for refinement.  R-factors based
on F² 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             2539
_reflns_number_gt                2081
_reflns_threshold_expression     >2sigma(I)

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_R_factor_all          0.0499
_refine_ls_R_factor_gt           0.0391
_refine_ls_wR_factor_gt          0.1022
_refine_ls_wR_factor_ref         0.1105
_refine_ls_goodness_of_fit_ref   1.045
_refine_ls_restrained_S_all      1.045
_refine_ls_number_reflns         2539
_refine_ls_number_parameters     174
_refine_ls_number_restraints     0
_refine_ls_hydrogen_treatment    constr
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0536P)²+5.5738P] where P=(Fo²+2Fc²)/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         3.840
_refine_diff_density_min         -1.874
_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'
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 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 0.91329(3) 0.37149(3) -0.09260(3) 0.02089(16) Uani d . 1 . .
Br Br1 1.01209(10) 0.36249(9) -0.23337(9) 0.0350(3) Uani d . 1 . .
C C1 0.8222(8) 0.3785(7) 0.0190(7) 0.0186(18) Uani d . 1 . .
N N2 0.7434(7) 0.4726(6) 0.0320(6) 0.0204(16) Uani d . 1 . .
C C7 0.7096(8) 0.5820(8) -0.0262(7) 0.025(2) Uani d . 1 . .
H H7 0.7424 0.5976 -0.0844 0.03 Uiso calc R 1 . .
C C6 0.6314(9) 0.6649(8) -0.0006(8) 0.028(2) Uani d . 1 . .
H H6 0.6087 0.739 -0.0409 0.034 Uiso calc R 1 . .
C C5 0.5820(9) 0.6431(9) 0.0861(8) 0.033(3) Uani d . 1 . .
H H5 0.5284 0.7039 0.1046 0.039 Uiso calc R 1 . .
C C4 0.6101(9) 0.5371(9) 0.1430(7) 0.030(2) Uani d . 1 . .
H H4 0.5743 0.5226 0.1997 0.035 Uiso calc R 1 . .
C C3 0.6935(8) 0.4472(8) 0.1176(7) 0.0226(19) Uani d . 1 . .
C C2 0.7449(8) 0.3346(8) 0.1561(7) 0.025(2) Uani d . 1 . .
H H2 0.7314 0.2911 0.2146 0.03 Uiso calc R 1 . .
N N1 0.8201(6) 0.2966(6) 0.0934(6) 0.0211(16) Uani d . 1 . .
C C8 0.8937(8) 0.1802(7) 0.1092(7) 0.0204(18) Uani d . 1 . .
C C9 1.0265(8) 0.1837(8) 0.1644(7) 0.0221(19) Uani d . 1 . .
C C14 1.0967(9) 0.3013(9) 0.2101(8) 0.033(2) Uani d . 1 . .
H H14A 1.0897 0.3606 0.1523 0.05 Uiso calc R 1 . .
H H14B 1.19 0.2835 0.2466 0.05 Uiso calc R 1 . .
H H14C 1.0562 0.3365 0.261 0.05 Uiso calc R 1 . .
C C10 1.0977(9) 0.0723(8) 0.1777(7) 0.025(2) Uani d . 1 . .
H H10 1.1903 0.072 0.2127 0.03 Uiso calc R 1 . .
C C11 1.0316(10) -0.0384(9) 0.1392(8) 0.032(2) Uani d . 1 . .
H H11 1.0795 -0.1138 0.1481 0.038 Uiso calc R 1 . .
C C12 0.8967(10) -0.0383(9) 0.0883(8) 0.031(2) Uani d . 1 . .
H H12 0.8529 -0.1143 0.0644 0.037 Uiso calc R 1 . .
C C13 0.8245(8) 0.0702(8) 0.0714(7) 0.0231(19) Uani d . 1 . .
C C15 0.6769(10) 0.0722(10) 0.0123(9) 0.046(3) Uani d . 1 . .
H H15A 0.6488 -0.0096 -0.0183 0.069 Uiso calc R 1 . .
H H15B 0.6585 0.1338 -0.045 0.069 Uiso calc R 1 . .
H H15C 0.6285 0.0938 0.0622 0.069 Uiso calc R 1 . .


_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 . 1.997(8) ?
Au1 Br1 . 2.4006(11) ?
C1 N1 . 1.327(11) ?
C1 N2 . 1.362(10) ?
N2 C7 . 1.396(11) ?
N2 C3 . 1.414(11) ?
C7 C6 . 1.336(13) ?
C7 H7 . 0.95 ?
C6 C5 . 1.418(14) ?
C6 H6 . 0.95 ?
C5 C4 . 1.352(13) ?
C5 H5 . 0.95 ?
C4 C3 . 1.425(12) ?
C4 H4 . 0.95 ?
C3 C2 . 1.367(13) ?
C2 N1 . 1.379(11) ?
C2 H2 . 0.95 ?
N1 C8 . 1.464(10) ?
C8 C9 . 1.377(12) ?
C8 C13 . 1.406(12) ?
C9 C10 . 1.405(13) ?
C9 C14 . 1.503(12) ?
C14 H14A . 0.98 ?
C14 H14B . 0.98 ?
C14 H14C . 0.98 ?
C10 C11 . 1.403(13) ?
C10 H10 . 0.95 ?
C11 C12 . 1.385(13) ?
C11 H11 . 0.95 ?
C12 C13 . 1.382(13) ?
C12 H12 . 0.95 ?
C13 C15 . 1.523(13) ?
C15 H15A . 0.98 ?
C15 H15B . 0.98 ?
C15 H15C . 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 Br1 . . 177.1(2) ?
N1 C1 N2 . . 104.7(7) ?
N1 C1 Au1 . . 129.9(6) ?
N2 C1 Au1 . . 125.4(6) ?
C1 N2 C7 . . 128.9(7) ?
C1 N2 C3 . . 110.7(7) ?
C7 N2 C3 . . 120.4(7) ?
C6 C7 N2 . . 120.4(9) ?
C6 C7 H7 . . 119.8 ?
N2 C7 H7 . . 119.8 ?
C7 C6 C5 . . 120.4(9) ?
C7 C6 H6 . . 119.8 ?
C5 C6 H6 . . 119.8 ?
C4 C5 C6 . . 121.0(8) ?
C4 C5 H5 . . 119.5 ?
C6 C5 H5 . . 119.5 ?
C5 C4 C3 . . 119.7(8) ?
C5 C4 H4 . . 120.2 ?
C3 C4 H4 . . 120.2 ?
C2 C3 N2 . . 105.3(7) ?
C2 C3 C4 . . 136.7(8) ?
N2 C3 C4 . . 118.0(8) ?
C3 C2 N1 . . 106.4(8) ?
C3 C2 H2 . . 126.8 ?
N1 C2 H2 . . 126.8 ?
C1 N1 C2 . . 112.9(7) ?
C1 N1 C8 . . 123.3(7) ?
C2 N1 C8 . . 123.8(7) ?
C9 C8 C13 . . 123.4(8) ?
C9 C8 N1 . . 117.9(7) ?
C13 C8 N1 . . 118.6(7) ?
C8 C9 C10 . . 117.9(8) ?
C8 C9 C14 . . 122.5(8) ?
C10 C9 C14 . . 119.5(8) ?
C9 C14 H14A . . 109.5 ?
C9 C14 H14B . . 109.5 ?
H14A C14 H14B . . 109.5 ?
C9 C14 H14C . . 109.5 ?
H14A C14 H14C . . 109.5 ?
H14B C14 H14C . . 109.5 ?
C11 C10 C9 . . 119.7(8) ?
C11 C10 H10 . . 120.1 ?
C9 C10 H10 . . 120.1 ?
C12 C11 C10 . . 120.3(8) ?
C12 C11 H11 . . 119.9 ?
C10 C11 H11 . . 119.9 ?
C13 C12 C11 . . 121.4(8) ?
C13 C12 H12 . . 119.3 ?
C11 C12 H12 . . 119.3 ?
C12 C13 C8 . . 117.2(8) ?
C12 C13 C15 . . 121.9(8) ?
C8 C13 C15 . . 120.9(8) ?
C13 C15 H15A . . 109.5 ?
C13 C15 H15B . . 109.5 ?
H15A C15 H15B . . 109.5 ?
C13 C15 H15C . . 109.5 ?
H15A C15 H15C . . 109.5 ?
H15B C15 H15C . . 109.5 ?

_database_code_depnum_ccdc_archive 'CCDC 985737'
#######################################################################
#
#                 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        
'Bis{2-(2,6-diisopropylphenyl)imidazo[1,5-a]pyridin-3-ylidene}gold(I) PF6'
_chemical_name_common            ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C38 H44 Au F6 N4 P'
_chemical_formula_iupac          ?
_chemical_formula_weight         898.71

_chemical_melting_point          ?

_space_group_crystal_system      triclinic
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   8.6606(9)
_cell_length_b                   10.3644(11)
_cell_length_c                   11.0776(13)
_cell_angle_alpha                83.862(4)
_cell_angle_beta                 74.229(3)
_cell_angle_gamma                80.572(4)
_cell_volume                     941.95(18)
_cell_formula_units_Z            1
_cell_measurement_reflns_used    9655
_cell_measurement_theta_min      2.4683
_cell_measurement_theta_max      25.4758
_cell_measurement_temperature    200.(2)

_exptl_crystal_description       plate
_exptl_crystal_colour            yellow
_exptl_crystal_size_max          0.600
_exptl_crystal_size_mid          0.400
_exptl_crystal_size_min          0.050
_exptl_crystal_density_diffrn    1.584
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             448

_exptl_absorpt_coefficient_mu    4.009
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS V2012/1 (Bruker AXS Inc.)'
_exptl_absorpt_correction_T_min  0.49
_exptl_absorpt_correction_T_max  0.82

_exptl_special_details           
;
;

_diffrn_ambient_temperature      200.(2)

_diffrn_source                   ?
_diffrn_source_type              ?

_diffrn_radiation_type           ?
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_monochromator  ?

_diffrn_measurement_device_type  ?
_diffrn_measurement_method       ?

_diffrn_detector_area_resol_mean 8.3330

_diffrn_reflns_number            75271
_diffrn_reflns_av_R_equivalents  0.0502
_diffrn_reflns_av_sigmaI/netI    0.0176
_diffrn_reflns_theta_min         2.47
_diffrn_reflns_theta_max         27.08
_diffrn_reflns_theta_full        27.08
_diffrn_measured_fraction_theta_max 0.981
_diffrn_measured_fraction_theta_full 0.981
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_limit_l_max       14

_refine_special_details          
;
Refinement of F² against ALL reflections.  The weighted R-factor wR and
goodness of fit S are based on F², conventional R-factors R are based
on F, with F set to zero for negative F². The threshold expression of
F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is
not relevant to the choice of reflections for refinement.  R-factors based
on F² 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             4071
_reflns_number_gt                4068
_reflns_threshold_expression     >2sigma(I)

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_R_factor_all          0.0376
_refine_ls_R_factor_gt           0.0375
_refine_ls_wR_factor_gt          0.0933
_refine_ls_wR_factor_ref         0.0935
_refine_ls_goodness_of_fit_ref   1.028
_refine_ls_restrained_S_all      1.028
_refine_ls_number_reflns         4071
_refine_ls_number_parameters     233
_refine_ls_number_restraints     0
_refine_ls_hydrogen_treatment    constr
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0448P)²+5.4261P] where P=(Fo²+2Fc²)/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         3.885
_refine_diff_density_min         -1.054
_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'
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 (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 0 0.5 0.02820(9) Uani d S 1 . .
P P1 0.5 0.5 0 0.0451(5) Uani d S 1 . .
F F1 0.5312(11) 0.5054(7) 0.1321(6) 0.124(3) Uani d . 1 . .
F F2 0.5445(7) 0.6443(4) -0.0363(4) 0.0818(15) Uani d . 1 . .
F F3 0.6815(7) 0.4468(6) -0.0628(7) 0.122(3) Uani d . 1 . .
N N2 0.2241(5) 0.1765(4) 0.3347(3) 0.0240(7) Uani d . 1 . .
N N1 0.1177(5) 0.2629(4) 0.5104(4) 0.0319(9) Uani d . 1 . .
C C1 0.1162(6) 0.1581(4) 0.4466(4) 0.0262(9) Uani d . 1 . .
C C7 0.2935(6) 0.2888(5) 0.3258(4) 0.0303(9) Uani d . 1 . .
H H7 0.3719 0.3208 0.256 0.036 Uiso calc R 1 . .
C C2 0.2259(7) 0.3450(5) 0.4384(5) 0.0344(11) Uani d . 1 . .
C C3 0.2435(9) 0.4602(5) 0.4910(6) 0.0503(15) Uani d . 1 . .
H H3 0.317 0.5176 0.4449 0.06 Uiso calc R 1 . .
C C4 0.1518(11) 0.4850(7) 0.6095(7) 0.068(2) Uani d . 1 . .
H H4 0.1615 0.5614 0.6456 0.082 Uiso calc R 1 . .
C C5 0.0423(11) 0.4004(6) 0.6803(6) 0.062(2) Uani d . 1 . .
H H5 -0.0197 0.4211 0.7625 0.074 Uiso calc R 1 . .
C C6 0.0249(8) 0.2904(6) 0.6326(5) 0.0440(13) Uani d . 1 . .
H H6 -0.048 0.2333 0.6804 0.053 Uiso calc R 1 . .
C C9 0.2578(5) 0.0845(4) 0.2376(4) 0.0249(8) Uani d . 1 . .
C C10 0.1791(6) 0.1154(4) 0.1411(4) 0.0276(9) Uani d . 1 . .
C C11 0.2067(7) 0.0213(5) 0.0531(5) 0.0397(12) Uani d . 1 . .
H H11 0.156 0.0384 -0.0141 0.048 Uiso calc R 1 . .
C C12 0.3062(8) -0.0959(6) 0.0623(5) 0.0429(13) Uani d . 1 . .
H H12 0.3216 -0.1589 0.0022 0.051 Uiso calc R 1 . .
C C13 0.3834(7) -0.1226(5) 0.1576(5) 0.0381(11) Uani d . 1 . .
H H13 0.453 -0.203 0.1617 0.046 Uiso calc R 1 . .
C C14 0.3604(6) -0.0326(5) 0.2484(4) 0.0300(9) Uani d . 1 . .
C C15 0.4487(6) -0.0632(5) 0.3520(5) 0.0350(10) Uani d . 1 . .
H H15 0.4031 0.0049 0.4146 0.042 Uiso calc R 1 . .
C C16 0.4235(9) -0.1982(7) 0.4219(6) 0.0566(16) Uani d . 1 . .
H H16A 0.3072 -0.2028 0.4539 0.085 Uiso calc R 1 . .
H H16B 0.4738 -0.2101 0.4923 0.085 Uiso calc R 1 . .
H H16C 0.4734 -0.2674 0.3639 0.085 Uiso calc R 1 . .
C C8 0.6296(8) -0.0547(8) 0.2993(6) 0.0575(17) Uani d . 1 . .
H H8A 0.678 -0.1215 0.2386 0.086 Uiso calc R 1 . .
H H8B 0.6828 -0.0694 0.3682 0.086 Uiso calc R 1 . .
H H8C 0.6439 0.0324 0.2576 0.086 Uiso calc R 1 . .
C C17 0.0630(7) 0.2413(5) 0.1333(5) 0.0354(11) Uani d . 1 . .
H H17 0.0895 0.3074 0.1813 0.042 Uiso calc R 1 . .
C C18 -0.1111(8) 0.2168(6) 0.1953(6) 0.0488(14) Uani d . 1 . .
H H18A -0.137 0.1475 0.1536 0.073 Uiso calc R 1 . .
H H18B -0.1855 0.2975 0.1876 0.073 Uiso calc R 1 . .
H H18C -0.1223 0.1896 0.2844 0.073 Uiso calc R 1 . .
C C19 0.0769(9) 0.2988(6) -0.0017(6) 0.0548(16) Uani d . 1 . .
H H19A 0.1892 0.3128 -0.0415 0.082 Uiso calc R 1 . .
H H19B 0.0055 0.3827 -0.0008 0.082 Uiso calc R 1 . .
H H19C 0.0449 0.2378 -0.0491 0.082 Uiso calc R 1 . .


_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 . 2.014(5) ?
Au1 C1 2_556 2.014(5) ?
P1 F1 . 1.567(6) ?
P1 F1 2_665 1.568(6) ?
P1 F3 2_665 1.569(5) ?
P1 F3 . 1.569(5) ?
P1 F2 . 1.588(4) ?
P1 F2 2_665 1.588(4) ?
N2 C1 . 1.350(6) ?
N2 C7 . 1.378(6) ?
N2 C9 . 1.453(5) ?
N1 C1 . 1.362(6) ?
N1 C2 . 1.397(7) ?
N1 C6 . 1.405(7) ?
C7 C2 . 1.372(7) ?
C7 H7 . 0.95 ?
C2 C3 . 1.430(7) ?
C3 C4 . 1.363(11) ?
C3 H3 . 0.95 ?
C4 C5 . 1.416(12) ?
C4 H4 . 0.95 ?
C5 C6 . 1.353(9) ?
C5 H5 . 0.95 ?
C6 H6 . 0.95 ?
C9 C14 . 1.397(7) ?
C9 C10 . 1.400(6) ?
C10 C11 . 1.399(6) ?
C10 C17 . 1.522(7) ?
C11 C12 . 1.381(8) ?
C11 H11 . 0.95 ?
C12 C13 . 1.379(7) ?
C12 H12 . 0.95 ?
C13 C14 . 1.397(7) ?
C13 H13 . 0.95 ?
C14 C15 . 1.523(6) ?
C15 C8 . 1.530(8) ?
C15 C16 . 1.543(8) ?
C15 H15 . 1.0 ?
C16 H16A . 0.98 ?
C16 H16B . 0.98 ?
C16 H16C . 0.98 ?
C8 H8A . 0.98 ?
C8 H8B . 0.98 ?
C8 H8C . 0.98 ?
C17 C18 . 1.528(8) ?
C17 C19 . 1.530(8) ?
C17 H17 . 1.0 ?
C18 H18A . 0.98 ?
C18 H18B . 0.98 ?
C18 H18C . 0.98 ?
C19 H19A . 0.98 ?
C19 H19B . 0.98 ?
C19 H19C . 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 C1 . 2_556 180.0 ?
F1 P1 F1 . 2_665 180.0(6) ?
F1 P1 F3 . 2_665 86.5(5) ?
F1 P1 F3 2_665 2_665 93.5(5) ?
F1 P1 F3 . . 93.5(5) ?
F1 P1 F3 2_665 . 86.5(5) ?
F3 P1 F3 2_665 . 179.9990(10) ?
F1 P1 F2 . . 89.4(3) ?
F1 P1 F2 2_665 . 90.6(3) ?
F3 P1 F2 2_665 . 91.8(3) ?
F3 P1 F2 . . 88.2(3) ?
F1 P1 F2 . 2_665 90.6(3) ?
F1 P1 F2 2_665 2_665 89.4(3) ?
F3 P1 F2 2_665 2_665 88.2(3) ?
F3 P1 F2 . 2_665 91.8(3) ?
F2 P1 F2 . 2_665 179.9990(10) ?
C1 N2 C7 . . 112.7(4) ?
C1 N2 C9 . . 121.3(4) ?
C7 N2 C9 . . 125.9(4) ?
C1 N1 C2 . . 111.3(4) ?
C1 N1 C6 . . 126.7(5) ?
C2 N1 C6 . . 122.0(4) ?
N2 C1 N1 . . 104.0(4) ?
N2 C1 Au1 . . 124.8(3) ?
N1 C1 Au1 . . 131.1(3) ?
C2 C7 N2 . . 105.9(4) ?
C2 C7 H7 . . 127.1 ?
N2 C7 H7 . . 127.1 ?
C7 C2 N1 . . 106.1(4) ?
C7 C2 C3 . . 135.0(6) ?
N1 C2 C3 . . 118.9(5) ?
C4 C3 C2 . . 118.0(6) ?
C4 C3 H3 . . 121.0 ?
C2 C3 H3 . . 121.0 ?
C3 C4 C5 . . 122.0(6) ?
C3 C4 H4 . . 119.0 ?
C5 C4 H4 . . 119.0 ?
C6 C5 C4 . . 120.9(6) ?
C6 C5 H5 . . 119.5 ?
C4 C5 H5 . . 119.5 ?
C5 C6 N1 . . 118.2(6) ?
C5 C6 H6 . . 120.9 ?
N1 C6 H6 . . 120.9 ?
C14 C9 C10 . . 123.5(4) ?
C14 C9 N2 . . 118.5(4) ?
C10 C9 N2 . . 118.0(4) ?
C11 C10 C9 . . 116.6(4) ?
C11 C10 C17 . . 120.6(4) ?
C9 C10 C17 . . 122.7(4) ?
C12 C11 C10 . . 121.2(5) ?
C12 C11 H11 . . 119.4 ?
C10 C11 H11 . . 119.4 ?
C13 C12 C11 . . 120.7(5) ?
C13 C12 H12 . . 119.6 ?
C11 C12 H12 . . 119.6 ?
C12 C13 C14 . . 120.7(5) ?
C12 C13 H13 . . 119.6 ?
C14 C13 H13 . . 119.6 ?
C13 C14 C9 . . 117.3(4) ?
C13 C14 C15 . . 119.9(4) ?
C9 C14 C15 . . 122.8(4) ?
C14 C15 C8 . . 110.8(4) ?
C14 C15 C16 . . 112.4(5) ?
C8 C15 C16 . . 110.3(5) ?
C14 C15 H15 . . 107.7 ?
C8 C15 H15 . . 107.7 ?
C16 C15 H15 . . 107.7 ?
C15 C16 H16A . . 109.5 ?
C15 C16 H16B . . 109.5 ?
H16A C16 H16B . . 109.5 ?
C15 C16 H16C . . 109.5 ?
H16A C16 H16C . . 109.5 ?
H16B C16 H16C . . 109.5 ?
C15 C8 H8A . . 109.5 ?
C15 C8 H8B . . 109.5 ?
H8A C8 H8B . . 109.5 ?
C15 C8 H8C . . 109.5 ?
H8A C8 H8C . . 109.5 ?
H8B C8 H8C . . 109.5 ?
C10 C17 C18 . . 109.9(4) ?
C10 C17 C19 . . 112.9(5) ?
C18 C17 C19 . . 109.8(5) ?
C10 C17 H17 . . 108.1 ?
C18 C17 H17 . . 108.1 ?
C19 C17 H17 . . 108.1 ?
C17 C18 H18A . . 109.5 ?
C17 C18 H18B . . 109.5 ?
H18A C18 H18B . . 109.5 ?
C17 C18 H18C . . 109.5 ?
H18A C18 H18C . . 109.5 ?
H18B C18 H18C . . 109.5 ?
C17 C19 H19A . . 109.5 ?
C17 C19 H19B . . 109.5 ?
H19A C19 H19B . . 109.5 ?
C17 C19 H19C . . 109.5 ?
H19A C19 H19C . . 109.5 ?
H19B C19 H19C . . 109.5 ?

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
C7 N2 C1 N1 . . . . 0.0(5) ?
C9 N2 C1 N1 . . . . -179.7(4) ?
C7 N2 C1 Au1 . . . . -176.0(3) ?
C9 N2 C1 Au1 . . . . 4.3(6) ?
C2 N1 C1 N2 . . . . -0.1(5) ?
C6 N1 C1 N2 . . . . 179.7(4) ?
C2 N1 C1 Au1 . . . . 175.5(3) ?
C6 N1 C1 Au1 . . . . -4.7(7) ?
C1 Au1 C1 N2 2_556 . . . -30.(30) ?
C1 Au1 C1 N1 2_556 . . . 150.(30) ?
C1 N2 C7 C2 . . . . 0.0(5) ?
C9 N2 C7 C2 . . . . 179.7(4) ?
N2 C7 C2 N1 . . . . -0.1(5) ?
N2 C7 C2 C3 . . . . 179.8(6) ?
C1 N1 C2 C7 . . . . 0.1(5) ?
C6 N1 C2 C7 . . . . -179.7(4) ?
C1 N1 C2 C3 . . . . -179.8(5) ?
C6 N1 C2 C3 . . . . 0.4(7) ?
C7 C2 C3 C4 . . . . 179.4(6) ?
N1 C2 C3 C4 . . . . -0.7(8) ?
C2 C3 C4 C5 . . . . 0.4(10) ?
C3 C4 C5 C6 . . . . 0.1(11) ?
C4 C5 C6 N1 . . . . -0.4(9) ?
C1 N1 C6 C5 . . . . -179.6(5) ?
C2 N1 C6 C5 . . . . 0.2(8) ?
C1 N2 C9 C14 . . . . -78.6(6) ?
C7 N2 C9 C14 . . . . 101.8(5) ?
C1 N2 C9 C10 . . . . 98.4(5) ?
C7 N2 C9 C10 . . . . -81.2(6) ?
C14 C9 C10 C11 . . . . 0.5(7) ?
N2 C9 C10 C11 . . . . -176.3(4) ?
C14 C9 C10 C17 . . . . 177.8(5) ?
N2 C9 C10 C17 . . . . 0.9(7) ?
C9 C10 C11 C12 . . . . 0.2(8) ?
C17 C10 C11 C12 . . . . -177.1(5) ?
C10 C11 C12 C13 . . . . -1.0(10) ?
C11 C12 C13 C14 . . . . 1.2(9) ?
C12 C13 C14 C9 . . . . -0.5(8) ?
C12 C13 C14 C15 . . . . -179.2(5) ?
C10 C9 C14 C13 . . . . -0.4(7) ?
N2 C9 C14 C13 . . . . 176.4(4) ?
C10 C9 C14 C15 . . . . 178.3(4) ?
N2 C9 C14 C15 . . . . -4.9(7) ?
C13 C14 C15 C8 . . . . 71.6(7) ?
C9 C14 C15 C8 . . . . -107.0(6) ?
C13 C14 C15 C16 . . . . -52.4(7) ?
C9 C14 C15 C16 . . . . 129.0(5) ?
C11 C10 C17 C18 . . . . 82.7(6) ?
C9 C10 C17 C18 . . . . -94.5(5) ?
C11 C10 C17 C19 . . . . -40.2(7) ?
C9 C10 C17 C19 . . . . 142.7(5) ?

_database_code_depnum_ccdc_archive 'CCDC 985738'
#######################################################################
#
#                 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        
Tribromido-{2-(2,6-dimethylphenyl)imidazo[1,5-a]pyridin-3-ylidene}gold(III)
_chemical_name_common            ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C15 H14 Au Br3 N2'
_chemical_formula_iupac          ?
_chemical_formula_weight         658.98

_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                   9.591(2)
_cell_length_b                   14.252(3)
_cell_length_c                   12.728(3)
_cell_angle_alpha                90
_cell_angle_beta                 99.907(7)
_cell_angle_gamma                90
_cell_volume                     1713.9(6)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    1487
_cell_measurement_theta_min      2.46
_cell_measurement_theta_max      21.29
_cell_measurement_temperature    200.(2)

_exptl_crystal_description       plate
_exptl_crystal_colour            red
_exptl_crystal_size_max          0.63
_exptl_crystal_size_mid          0.24
_exptl_crystal_size_min          0.05
_exptl_crystal_density_diffrn    2.554
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1208

_exptl_absorpt_coefficient_mu    15.572
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS V2008/1 (Bruker AXS)'
_exptl_absorpt_correction_T_min  0.04
_exptl_absorpt_correction_T_max  0.51

_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 8.3330


_diffrn_reflns_number            10864
_diffrn_reflns_av_R_equivalents  0.0954
_diffrn_reflns_av_sigmaI/netI    0.0931
_diffrn_reflns_theta_min         2.16
_diffrn_reflns_theta_max         24.99
_diffrn_reflns_theta_full        24.99
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measured_fraction_theta_full 0.998
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_limit_l_max       15

_refine_special_details          
;
Refinement of F² against ALL reflections.  The weighted R-factor wR and
goodness of fit S are based on F², conventional R-factors R are based
on F, with F set to zero for negative F². The threshold expression of
F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is
not relevant to the choice of reflections for refinement.  R-factors based
on F² 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             3021
_reflns_number_gt                2122
_reflns_threshold_expression     >2sigma(I)

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_R_factor_all          0.0725
_refine_ls_R_factor_gt           0.0412
_refine_ls_wR_factor_gt          0.0804
_refine_ls_wR_factor_ref         0.0926
_refine_ls_goodness_of_fit_ref   0.994
_refine_ls_restrained_S_all      0.994
_refine_ls_number_reflns         3021
_refine_ls_number_parameters     192
_refine_ls_number_restraints     0
_refine_ls_hydrogen_treatment    constr
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0116P)²+0.0000P] where P=(Fo²+2Fc²)/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         1.021
_refine_diff_density_min         -0.959
_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'
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 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 0.84443(4) 0.21885(3) 0.82908(3) 0.02617(14) Uani d . 1 . .
Br Br1 0.93980(12) 0.10707(8) 0.96654(9) 0.0409(3) Uani d . 1 . .
Br Br2 0.72822(12) 0.31019(8) 0.67875(9) 0.0398(3) Uani d . 1 . .
Br Br3 1.07678(12) 0.23656(8) 0.77689(10) 0.0450(3) Uani d . 1 . .
N N2 0.5687(8) 0.1359(5) 0.8749(6) 0.023(2) Uani d . 1 . .
N N1 0.5976(9) 0.2774(5) 0.9337(6) 0.025(2) Uani d . 1 . .
C C1 0.6538(12) 0.2107(7) 0.8810(8) 0.032(3) Uani d . 1 . .
C C2 0.4532(10) 0.1569(7) 0.9222(7) 0.022(2) Uani d . 1 . .
C C3 0.4739(11) 0.2464(7) 0.9607(8) 0.034(3) Uani d . 1 . .
H H3 0.4136 0.2804 0.9989 0.041 Uiso calc R 1 . .
C C4 0.6541(10) 0.3713(6) 0.9505(8) 0.025(2) Uani d . 1 . .
C C5 0.5872(12) 0.4426(7) 0.8845(9) 0.037(3) Uani d . 1 . .
C C6 0.4581(11) 0.4246(8) 0.8011(8) 0.044(3) Uani d . 1 . .
H H6A 0.4831 0.3828 0.7461 0.067 Uiso calc R 1 . .
H H6B 0.4228 0.4842 0.7684 0.067 Uiso calc R 1 . .
H H6C 0.3844 0.3952 0.8345 0.067 Uiso calc R 1 . .
C C7 0.6463(13) 0.5325(7) 0.8985(9) 0.043(3) Uani d . 1 . .
H H7 0.6034 0.5828 0.8557 0.052 Uiso calc R 1 . .
C C8 0.7632(14) 0.5490(8) 0.9717(10) 0.053(4) Uani d . 1 . .
H H8 0.8041 0.6098 0.9766 0.064 Uiso calc R 1 . .
C C9 0.8250(13) 0.4788(8) 1.0401(10) 0.046(3) Uani d . 1 . .
H H9 0.9031 0.4933 1.0943 0.056 Uiso calc R 1 . .
C C10 0.7735(12) 0.3876(7) 1.0299(8) 0.034(3) Uani d . 1 . .
C C11 0.8408(12) 0.3138(8) 1.1055(8) 0.049(3) Uani d . 1 . .
H H11A 0.9328 0.2965 1.0876 0.074 Uiso calc R 1 . .
H H11B 0.7796 0.2583 1.1 0.074 Uiso calc R 1 . .
H H11C 0.8543 0.3381 1.1786 0.074 Uiso calc R 1 . .
C C12 0.3460(11) 0.0846(7) 0.9244(9) 0.037(3) Uani d . 1 . .
H H12 0.2663 0.0957 0.9578 0.044 Uiso calc R 1 . .
C C13 0.3637(12) 0.0004(7) 0.8769(9) 0.035(3) Uani d . 1 . .
H H13 0.2948 -0.0475 0.8771 0.042 Uiso calc R 1 . .
C C14 0.4811(14) -0.0168(7) 0.8281(9) 0.042(3) Uani d . 1 . .
H H14 0.4893 -0.0759 0.7953 0.051 Uiso calc R 1 . .
C C15 0.5842(11) 0.0489(7) 0.8262(8) 0.034(3) Uani d . 1 . .
H H15 0.6638 0.0362 0.7931 0.041 Uiso calc R 1 . .


_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 . 2.052(12) ?
Au1 Br2 . 2.4217(11) ?
Au1 Br1 . 2.4260(11) ?
Au1 Br3 . 2.4455(14) ?
N2 C1 . 1.338(12) ?
N2 C2 . 1.381(12) ?
N2 C15 . 1.406(12) ?
N1 C1 . 1.329(13) ?
N1 C3 . 1.365(13) ?
N1 C4 . 1.446(11) ?
C2 C3 . 1.368(13) ?
C2 C12 . 1.460(13) ?
C3 H3 . 0.95 ?
C4 C5 . 1.402(13) ?
C4 C10 . 1.410(13) ?
C5 C7 . 1.400(14) ?
C5 C6 . 1.508(14) ?
C6 H6A . 0.98 ?
C6 H6B . 0.98 ?
C6 H6C . 0.98 ?
C7 C8 . 1.349(15) ?
C7 H7 . 0.95 ?
C8 C9 . 1.390(15) ?
C8 H8 . 0.95 ?
C9 C10 . 1.389(14) ?
C9 H9 . 0.95 ?
C10 C11 . 1.495(14) ?
C11 H11A . 0.98 ?
C11 H11B . 0.98 ?
C11 H11C . 0.98 ?
C12 C13 . 1.367(14) ?
C12 H12 . 0.95 ?
C13 C14 . 1.397(15) ?
C13 H13 . 0.95 ?
C14 C15 . 1.365(15) ?
C14 H14 . 0.95 ?
C15 H15 . 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
C1 Au1 Br2 . . 88.3(3) ?
C1 Au1 Br1 . . 88.7(3) ?
Br2 Au1 Br1 . . 171.14(4) ?
C1 Au1 Br3 . . 176.0(3) ?
Br2 Au1 Br3 . . 92.69(4) ?
Br1 Au1 Br3 . . 90.89(4) ?
C1 N2 C2 . . 109.2(8) ?
C1 N2 C15 . . 128.3(10) ?
C2 N2 C15 . . 122.5(9) ?
C1 N1 C3 . . 110.0(9) ?
C1 N1 C4 . . 124.2(9) ?
C3 N1 C4 . . 125.6(9) ?
N1 C1 N2 . . 107.6(10) ?
N1 C1 Au1 . . 125.7(7) ?
N2 C1 Au1 . . 126.5(8) ?
C3 C2 N2 . . 106.3(9) ?
C3 C2 C12 . . 135.2(10) ?
N2 C2 C12 . . 118.4(9) ?
N1 C3 C2 . . 106.8(9) ?
N1 C3 H3 . . 126.6 ?
C2 C3 H3 . . 126.6 ?
C5 C4 C10 . . 122.8(9) ?
C5 C4 N1 . . 117.5(9) ?
C10 C4 N1 . . 119.7(8) ?
C7 C5 C4 . . 117.0(10) ?
C7 C5 C6 . . 120.7(10) ?
C4 C5 C6 . . 122.3(10) ?
C5 C6 H6A . . 109.5 ?
C5 C6 H6B . . 109.5 ?
H6A C6 H6B . . 109.5 ?
C5 C6 H6C . . 109.5 ?
H6A C6 H6C . . 109.5 ?
H6B C6 H6C . . 109.5 ?
C8 C7 C5 . . 121.1(11) ?
C8 C7 H7 . . 119.4 ?
C5 C7 H7 . . 119.4 ?
C7 C8 C9 . . 121.5(11) ?
C7 C8 H8 . . 119.3 ?
C9 C8 H8 . . 119.3 ?
C10 C9 C8 . . 120.5(11) ?
C10 C9 H9 . . 119.7 ?
C8 C9 H9 . . 119.7 ?
C9 C10 C4 . . 117.0(10) ?
C9 C10 C11 . . 119.4(10) ?
C4 C10 C11 . . 123.6(9) ?
C10 C11 H11A . . 109.5 ?
C10 C11 H11B . . 109.5 ?
H11A C11 H11B . . 109.5 ?
C10 C11 H11C . . 109.5 ?
H11A C11 H11C . . 109.5 ?
H11B C11 H11C . . 109.5 ?
C13 C12 C2 . . 118.0(11) ?
C13 C12 H12 . . 121.0 ?
C2 C12 H12 . . 121.0 ?
C12 C13 C14 . . 121.4(10) ?
C12 C13 H13 . . 119.3 ?
C14 C13 H13 . . 119.3 ?
C15 C14 C13 . . 122.0(11) ?
C15 C14 H14 . . 119.0 ?
C13 C14 H14 . . 119.0 ?
C14 C15 N2 . . 117.7(11) ?
C14 C15 H15 . . 121.2 ?
N2 C15 H15 . . 121.2 ?

_database_code_depnum_ccdc_archive 'CCDC 985739'
#######################################################################
#
#                 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        
Tribromido-{2-(2,6-diisopropylphenyl)imidazo[1,5-a]pyridin-3-ylidene}gold(III)
_chemical_name_common            ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C19 H22 Au Br3 N2'
_chemical_formula_iupac          ?
_chemical_formula_weight         715.08

_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                   10.005(4)
_cell_length_b                   13.609(5)
_cell_length_c                   16.219(6)
_cell_angle_alpha                90
_cell_angle_beta                 100.229(14)
_cell_angle_gamma                90
_cell_volume                     2173.2(14)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    6235
_cell_measurement_theta_min      2.22
_cell_measurement_theta_max      24.19
_cell_measurement_temperature    300.(2)

_exptl_crystal_description       cube
_exptl_crystal_colour            red
_exptl_crystal_size_max          0.45
_exptl_crystal_size_mid          0.44
_exptl_crystal_size_min          0.37
_exptl_crystal_density_diffrn    2.186
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1336

_exptl_absorpt_coefficient_mu    12.290
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS V2008/1 (Bruker AXS)'
_exptl_absorpt_correction_T_min  0.07
_exptl_absorpt_correction_T_max  0.09

_exptl_special_details           
;
;

_diffrn_ambient_temperature      300.(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 8.3330

_diffrn_reflns_number            23730
_diffrn_reflns_av_R_equivalents  0.0722
_diffrn_reflns_av_sigmaI/netI    0.0477
_diffrn_reflns_theta_min         2.23
_diffrn_reflns_theta_max         25.05
_diffrn_reflns_theta_full        25.05
_diffrn_measured_fraction_theta_max 0.994
_diffrn_measured_fraction_theta_full 0.994
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_limit_l_max       19

_refine_special_details          
;
Refinement of F² against ALL reflections.  The weighted R-factor wR and
goodness of fit S are based on F², conventional R-factors R are based
on F, with F set to zero for negative F². The threshold expression of
F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is
not relevant to the choice of reflections for refinement.  R-factors based
on F² 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             3826
_reflns_number_gt                3065
_reflns_threshold_expression     >2sigma(I)

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_R_factor_all          0.0439
_refine_ls_R_factor_gt           0.0296
_refine_ls_wR_factor_gt          0.0619
_refine_ls_wR_factor_ref         0.0671
_refine_ls_goodness_of_fit_ref   1.010
_refine_ls_restrained_S_all      1.010
_refine_ls_number_reflns         3826
_refine_ls_number_parameters     230
_refine_ls_number_restraints     0
_refine_ls_hydrogen_treatment    constr
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0215P)²+1.8689P] where P=(Fo²+2Fc²)/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         0.933
_refine_diff_density_min         -1.138
_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'
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 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 Br2 0.04953(7) 0.78494(5) 0.48398(4) 0.05076(18) Uani d . 1 . .
Au Au1 -0.02153(2) 0.645276(16) 0.559103(13) 0.03417(9) Uani d . 1 . .
Br Br3 -0.23244(7) 0.63274(6) 0.45788(4) 0.0598(2) Uani d . 1 . .
Br Br1 -0.08268(7) 0.50146(5) 0.63073(4) 0.0589(2) Uani d . 1 . .
C C16 0.0181(9) 0.4572(6) 0.8562(5) 0.085(3) Uani d . 1 . .
H H16A -0.0271 0.4645 0.9033 0.128 Uiso calc R 1 . .
H H16B 0.0791 0.4022 0.8654 0.128 Uiso calc R 1 . .
H H16C -0.048 0.4462 0.8064 0.128 Uiso calc R 1 . .
C C15 0.2056(8) 0.5651(6) 0.9253(4) 0.076(2) Uani d . 1 . .
H H15A 0.2695 0.6142 0.9151 0.115 Uiso calc R 1 . .
H H15B 0.2523 0.5042 0.94 0.115 Uiso calc R 1 . .
H H15C 0.1619 0.5859 0.9704 0.115 Uiso calc R 1 . .
N N1 0.1537(4) 0.6975(3) 0.7254(3) 0.0305(10) Uani d . 1 . .
N N2 0.2778(4) 0.6617(3) 0.6343(3) 0.0320(11) Uani d . 1 . .
C C6 0.4615(6) 0.6360(5) 0.5646(4) 0.058(2) Uani d . 1 . .
H H6 0.4956 0.6158 0.5176 0.07 Uiso calc R 1 . .
C C4 0.5064(6) 0.6993(5) 0.7039(4) 0.0500(17) Uani d . 1 . .
H H4 0.5669 0.721 0.7506 0.06 Uiso calc R 1 . .
C C9 0.0143(6) 0.6421(5) 0.8256(4) 0.0469(16) Uani d . 1 . .
C C13 -0.0334(6) 0.8002(5) 0.7529(4) 0.0459(16) Uani d . 1 . .
C C1 0.1472(5) 0.6634(4) 0.6467(3) 0.0324(13) Uani d . 1 . .
C C2 0.2848(5) 0.7187(4) 0.7615(4) 0.0359(13) Uani d . 1 . .
H H2 0.3135 0.7438 0.815 0.043 Uiso calc R 1 . .
C C7 0.3269(6) 0.6315(4) 0.5634(4) 0.0424(15) Uani d . 1 . .
H H7 0.2682 0.6087 0.5164 0.051 Uiso calc R 1 . .
C C5 0.5524(7) 0.6707(5) 0.6352(5) 0.0599(19) Uani d . 1 . .
H H5 0.6449 0.6737 0.634 0.072 Uiso calc R 1 . .
C C8 0.0384(5) 0.7130(4) 0.7680(3) 0.0364(14) Uani d . 1 . .
C C3 0.3644(5) 0.6965(4) 0.7055(4) 0.0367(14) Uani d . 1 . .
C C14 0.0982(7) 0.5504(5) 0.8457(4) 0.0557(18) Uani d . 1 . .
H H14 0.1468 0.5391 0.7992 0.067 Uiso calc R 1 . .
C C12 -0.1393(7) 0.8163(6) 0.7982(5) 0.065(2) Uani d . 1 . .
H H12 -0.191 0.8734 0.7897 0.078 Uiso calc R 1 . .
C C10 -0.0927(7) 0.6622(6) 0.8685(4) 0.066(2) Uani d . 1 . .
H H10 -0.1146 0.6169 0.9069 0.079 Uiso calc R 1 . .
C C11 -0.1656(8) 0.7481(7) 0.8544(5) 0.074(2) Uani d . 1 . .
H H11 -0.2351 0.7599 0.8843 0.089 Uiso calc R 1 . .
C C17 0.0016(7) 0.8793(5) 0.6951(4) 0.0512(17) Uani d . 1 . .
H H17 0.0545 0.8486 0.6567 0.061 Uiso calc R 1 . .
C C18 0.0911(9) 0.9570(6) 0.7450(5) 0.082(3) Uani d . 1 . .
H H18A 0.0435 0.9863 0.7852 0.124 Uiso calc R 1 . .
H H18B 0.1132 1.0067 0.7076 0.124 Uiso calc R 1 . .
H H18C 0.1732 0.9269 0.7737 0.124 Uiso calc R 1 . .
C C19 -0.1227(8) 0.9273(7) 0.6420(5) 0.102(3) Uani d . 1 . .
H H19A -0.1768 0.8778 0.6096 0.153 Uiso calc R 1 . .
H H19B -0.0937 0.9747 0.6051 0.153 Uiso calc R 1 . .
H H19C -0.1756 0.9594 0.678 0.153 Uiso calc R 1 . .


_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
Br2 Au1 . 2.4311(9) ?
Au1 C1 . 2.020(6) ?
Au1 Br1 . 2.4097(9) ?
Au1 Br3 . 2.4385(10) ?
C16 C14 . 1.526(9) ?
C16 H16A . 0.96 ?
C16 H16B . 0.96 ?
C16 H16C . 0.96 ?
C15 C14 . 1.539(9) ?
C15 H15A . 0.96 ?
C15 H15B . 0.96 ?
C15 H15C . 0.96 ?
N1 C1 . 1.348(7) ?
N1 C2 . 1.368(7) ?
N1 C8 . 1.462(6) ?
N2 C1 . 1.358(6) ?
N2 C7 . 1.390(7) ?
N2 C3 . 1.399(7) ?
C6 C7 . 1.345(8) ?
C6 C5 . 1.412(9) ?
C6 H6 . 0.93 ?
C4 C5 . 1.336(9) ?
C4 C3 . 1.425(7) ?
C4 H4 . 0.93 ?
C9 C8 . 1.393(8) ?
C9 C10 . 1.403(9) ?
C9 C14 . 1.506(9) ?
C13 C8 . 1.386(8) ?
C13 C12 . 1.410(8) ?
C13 C17 . 1.509(9) ?
C2 C3 . 1.344(7) ?
C2 H2 . 0.93 ?
C7 H7 . 0.93 ?
C5 H5 . 0.93 ?
C14 H14 . 0.98 ?
C12 C11 . 1.358(11) ?
C12 H12 . 0.93 ?
C10 C11 . 1.375(11) ?
C10 H10 . 0.93 ?
C11 H11 . 0.93 ?
C17 C18 . 1.522(9) ?
C17 C19 . 1.527(9) ?
C17 H17 . 0.98 ?
C18 H18A . 0.96 ?
C18 H18B . 0.96 ?
C18 H18C . 0.96 ?
C19 H19A . 0.96 ?
C19 H19B . 0.96 ?
C19 H19C . 0.96 ?

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 Br1 . . 90.69(15) ?
C1 Au1 Br2 . . 88.56(15) ?
Br1 Au1 Br2 . . 176.84(3) ?
C1 Au1 Br3 . . 176.00(15) ?
Br1 Au1 Br3 . . 90.25(3) ?
Br2 Au1 Br3 . . 90.71(3) ?
C14 C16 H16A . . 109.5 ?
C14 C16 H16B . . 109.5 ?
H16A C16 H16B . . 109.5 ?
C14 C16 H16C . . 109.5 ?
H16A C16 H16C . . 109.5 ?
H16B C16 H16C . . 109.5 ?
C14 C15 H15A . . 109.5 ?
C14 C15 H15B . . 109.5 ?
H15A C15 H15B . . 109.5 ?
C14 C15 H15C . . 109.5 ?
H15A C15 H15C . . 109.5 ?
H15B C15 H15C . . 109.5 ?
C1 N1 C2 . . 111.0(4) ?
C1 N1 C8 . . 125.9(4) ?
C2 N1 C8 . . 123.0(4) ?
C1 N2 C7 . . 128.3(5) ?
C1 N2 C3 . . 110.0(4) ?
C7 N2 C3 . . 121.7(5) ?
C7 C6 C5 . . 121.7(6) ?
C7 C6 H6 . . 119.1 ?
C5 C6 H6 . . 119.1 ?
C5 C4 C3 . . 120.0(6) ?
C5 C4 H4 . . 120.0 ?
C3 C4 H4 . . 120.0 ?
C8 C9 C10 . . 115.8(6) ?
C8 C9 C14 . . 124.2(5) ?
C10 C9 C14 . . 120.0(6) ?
C8 C13 C12 . . 117.0(6) ?
C8 C13 C17 . . 123.4(5) ?
C12 C13 C17 . . 119.4(6) ?
N1 C1 N2 . . 105.1(5) ?
N1 C1 Au1 . . 127.0(4) ?
N2 C1 Au1 . . 126.8(4) ?
C3 C2 N1 . . 107.6(5) ?
C3 C2 H2 . . 126.2 ?
N1 C2 H2 . . 126.2 ?
C6 C7 N2 . . 118.4(6) ?
C6 C7 H7 . . 120.8 ?
N2 C7 H7 . . 120.8 ?
C4 C5 C6 . . 120.4(6) ?
C4 C5 H5 . . 119.8 ?
C6 C5 H5 . . 119.8 ?
C13 C8 C9 . . 124.4(5) ?
C13 C8 N1 . . 117.8(5) ?
C9 C8 N1 . . 117.6(5) ?
C2 C3 N2 . . 106.2(5) ?
C2 C3 C4 . . 136.0(6) ?
N2 C3 C4 . . 117.8(5) ?
C9 C14 C16 . . 115.4(6) ?
C9 C14 C15 . . 110.7(6) ?
C16 C14 C15 . . 108.4(6) ?
C9 C14 H14 . . 107.3 ?
C16 C14 H14 . . 107.3 ?
C15 C14 H14 . . 107.3 ?
C11 C12 C13 . . 119.8(7) ?
C11 C12 H12 . . 120.1 ?
C13 C12 H12 . . 120.1 ?
C11 C10 C9 . . 120.8(7) ?
C11 C10 H10 . . 119.6 ?
C9 C10 H10 . . 119.6 ?
C12 C11 C10 . . 122.2(7) ?
C12 C11 H11 . . 118.9 ?
C10 C11 H11 . . 118.9 ?
C13 C17 C18 . . 110.2(6) ?
C13 C17 C19 . . 113.6(6) ?
C18 C17 C19 . . 110.3(6) ?
C13 C17 H17 . . 107.5 ?
C18 C17 H17 . . 107.5 ?
C19 C17 H17 . . 107.5 ?
C17 C18 H18A . . 109.5 ?
C17 C18 H18B . . 109.5 ?
H18A C18 H18B . . 109.5 ?
C17 C18 H18C . . 109.5 ?
H18A C18 H18C . . 109.5 ?
H18B C18 H18C . . 109.5 ?
C17 C19 H19A . . 109.5 ?
C17 C19 H19B . . 109.5 ?
H19A C19 H19B . . 109.5 ?
C17 C19 H19C . . 109.5 ?
H19A C19 H19C . . 109.5 ?
H19B C19 H19C . . 109.5 ?

_database_code_depnum_ccdc_archive 'CCDC 985740'
