# Electronic Supplementary Material (ESI) for CrystEngComm.
# 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_d:\determination\solution\754\kh754-abs1

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C12 H9 Br1 Hg1 I2 N2 O1'
_chemical_formula_weight         731.50

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'
O O 0.0106 0.0060 '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'
Hg Hg -2.3894 9.2266 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
I I -0.4742 1.8119 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_symmetry_cell_setting           Monoclinic
_symmetry_space_group_name_H-M   C2/c

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

_cell_length_a                   25.3903(15)
_cell_length_b                   14.1304(6)
_cell_length_c                   9.1996(6)
_cell_angle_alpha                90.00
_cell_angle_beta                 99.658(5)
_cell_angle_gamma                90.00
_cell_volume                     3253.8(3)
_cell_formula_units_Z            8
_cell_measurement_temperature    298(2)
_cell_measurement_reflns_used    13230
_cell_measurement_theta_min      1.63
_cell_measurement_theta_max      26.00

_exptl_crystal_description       Block
_exptl_crystal_colour            Colorless
_exptl_crystal_size_max          0.35
_exptl_crystal_size_mid          0.12
_exptl_crystal_size_min          0.11
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    2.987
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             2592
_exptl_absorpt_coefficient_mu    15.705
_exptl_absorpt_correction_type   numerical
_exptl_absorpt_correction_T_min  0.0370
_exptl_absorpt_correction_T_max  0.1948
_exptl_absorpt_process_details   'shape of crystal determined optically'

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      298(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'STOE IPDS II'
_diffrn_measurement_method       'rotation method'
_diffrn_detector_area_resol_mean '0.15 mm'
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            13230
_diffrn_reflns_av_R_equivalents  0.0985
_diffrn_reflns_av_sigmaI/netI    0.0827
_diffrn_reflns_limit_h_min       -31
_diffrn_reflns_limit_h_max       31
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_theta_min         1.63
_diffrn_reflns_theta_max         26.00
_reflns_number_total             3201
_reflns_number_gt                2328
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'X-Area 1.31 (Stoe & Cie GmbH, 2005)'
_computing_cell_refinement       'X-Area 1.31 (Stoe & Cie GmbH, 2005)'
_computing_data_reduction        'X-Area 1.31 (Stoe & Cie GmbH, 2005)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    'ORTEP-3 for Windows (Farrugia, 1997)'
_computing_publication_material  'WinGX (Farrugia, 1999)'

_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. 
;

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0738P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         3201
_refine_ls_number_parameters     172
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0862
_refine_ls_R_factor_gt           0.0640
_refine_ls_wR_factor_ref         0.1517
_refine_ls_wR_factor_gt          0.1406
_refine_ls_goodness_of_fit_ref   1.023
_refine_ls_restrained_S_all      1.023
_refine_ls_shift/su_max          0.006
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C 0.3130(5) 0.3574(8) 0.4221(10) 0.035(2) Uani 1 1 d . . .
H1 H 0.3067 0.4166 0.3784 0.042 Uiso 1 1 calc R . .
C2 C 0.2942(5) 0.2763(9) 0.3466(11) 0.044(3) Uani 1 1 d . . .
H2 H 0.2747 0.2802 0.2518 0.053 Uiso 1 1 calc R . .
C3 C 0.3047(5) 0.1900(9) 0.4133(11) 0.041(3) Uani 1 1 d . . .
H3 H 0.2916 0.1357 0.3624 0.050 Uiso 1 1 calc R . .
C4 C 0.3506(5) 0.2599(8) 0.6244(10) 0.036(2) Uani 1 1 d . . .
H4 H 0.3693 0.2540 0.7200 0.043 Uiso 1 1 calc R . .
C5 C 0.3416(4) 0.3493(8) 0.5644(10) 0.032(2) Uani 1 1 d . . .
C6 C 0.3621(5) 0.4303(8) 0.6612(10) 0.032(2) Uani 1 1 d . . .
C7 C 0.3981(4) 0.5899(7) 0.6730(10) 0.031(2) Uani 1 1 d . . .
C8 C 0.4329(4) 0.5856(9) 0.8053(11) 0.040(3) Uani 1 1 d . . .
H8 H 0.4441 0.5274 0.8468 0.048 Uiso 1 1 calc R . .
C9 C 0.4508(4) 0.6693(9) 0.8755(11) 0.038(2) Uani 1 1 d . . .
C10 C 0.4379(6) 0.7560(10) 0.8133(15) 0.053(3) Uani 1 1 d . . .
H10 H 0.4510 0.8113 0.8607 0.063 Uiso 1 1 calc R . .
C11 C 0.4048(6) 0.7590(9) 0.6784(14) 0.054(3) Uani 1 1 d . . .
H11 H 0.3958 0.8174 0.6349 0.064 Uiso 1 1 calc R . .
C12 C 0.3854(5) 0.6803(9) 0.6081(12) 0.046(3) Uani 1 1 d . . .
H12 H 0.3636 0.6847 0.5165 0.056 Uiso 1 1 calc R . .
O1 O 0.3646(5) 0.4225(6) 0.7954(8) 0.057(3) Uani 1 1 d . . .
N1 N 0.3332(4) 0.1809(7) 0.5490(9) 0.039(2) Uani 1 1 d . . .
N2 N 0.3771(4) 0.5080(6) 0.5967(8) 0.034(2) Uani 1 1 d . . .
H2B H 0.3738 0.5081 0.5022 0.041 Uiso 1 1 calc R . .
Br1 Br 0.49487(6) 0.66192(13) 1.06384(15) 0.0650(4) Uani 1 1 d . . .
Hg1 Hg 0.35142(2) 0.02430(4) 0.64515(6) 0.0566(2) Uani 1 1 d . . .
I1 I 0.42908(4) 0.03706(7) 0.87066(9) 0.0575(3) Uani 1 1 d . . .
I2 I 0.27297(4) -0.07620(7) 0.49607(10) 0.0597(3) Uani 1 1 d . . .

loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_23
_atom_site_aniso_U_13
_atom_site_aniso_U_12
C1 0.045(6) 0.033(6) 0.026(4) 0.006(4) 0.001(4) 0.016(5)
C2 0.057(8) 0.042(7) 0.030(5) 0.007(5) 0.001(5) 0.004(6)
C3 0.057(7) 0.035(6) 0.030(5) -0.001(5) 0.003(5) -0.008(6)
C4 0.053(7) 0.032(6) 0.021(4) 0.001(4) 0.003(4) -0.006(5)
C5 0.032(6) 0.037(6) 0.027(4) 0.000(4) 0.010(4) 0.002(5)
C6 0.045(6) 0.028(5) 0.024(4) -0.002(4) 0.008(4) 0.001(5)
C7 0.044(6) 0.022(5) 0.031(4) 0.007(4) 0.017(4) 0.002(5)
C8 0.035(6) 0.052(7) 0.034(5) 0.002(5) 0.011(5) 0.001(5)
C9 0.028(5) 0.050(7) 0.037(5) -0.004(5) 0.009(4) 0.003(5)
C10 0.052(8) 0.045(8) 0.061(7) -0.017(6) 0.010(6) -0.012(6)
C11 0.067(9) 0.034(7) 0.060(7) -0.003(6) 0.012(7) 0.013(7)
C12 0.061(8) 0.039(7) 0.039(5) 0.008(5) 0.011(6) 0.007(6)
O1 0.115(8) 0.036(5) 0.023(3) -0.001(3) 0.016(4) -0.013(5)
N1 0.049(6) 0.028(5) 0.037(4) 0.006(4) -0.001(4) 0.003(4)
N2 0.051(6) 0.030(5) 0.022(3) 0.001(3) 0.006(4) 0.004(4)
Br1 0.0579(9) 0.0801(11) 0.0518(7) -0.0083(7) -0.0059(6) -0.0133(8)
Hg1 0.0616(4) 0.0346(3) 0.0637(3) 0.0033(2) -0.0178(2) -0.0026(2)
I1 0.0540(5) 0.0636(6) 0.0497(5) -0.0089(4) -0.0062(4) 0.0039(5)
I2 0.0545(6) 0.0475(5) 0.0698(5) -0.0100(4) -0.0109(4) -0.0048(4)

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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
C1 C2 1.384(16) . ?
C1 C5 1.391(14) . ?
C1 H1 0.9300 . ?
C2 C3 1.371(17) . ?
C2 H2 0.9300 . ?
C3 N1 1.340(14) . ?
C3 H3 0.9300 . ?
C4 N1 1.349(14) . ?
C4 C5 1.382(16) . ?
C4 H4 0.9300 . ?
C5 C6 1.490(15) . ?
C6 O1 1.231(11) . ?
C6 N2 1.332(14) . ?
C7 C8 1.381(15) . ?
C7 N2 1.411(14) . ?
C7 C12 1.423(15) . ?
C8 C9 1.388(17) . ?
C8 H8 0.9300 . ?
C9 C10 1.368(19) . ?
C9 Br1 1.901(11) . ?
C10 C11 1.376(19) . ?
C10 H10 0.9300 . ?
C11 C12 1.338(19) . ?
C11 H11 0.9300 . ?
C12 H12 0.9300 . ?
N1 Hg1 2.399(9) . ?
N2 H2B 0.8600 . ?
Hg1 I1 2.6176(10) . ?
Hg1 I2 2.6359(10) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C2 C1 C5 119.1(10) . . ?
C2 C1 H1 120.5 . . ?
C5 C1 H1 120.5 . . ?
C3 C2 C1 119.2(10) . . ?
C3 C2 H2 120.4 . . ?
C1 C2 H2 120.4 . . ?
N1 C3 C2 122.4(11) . . ?
N1 C3 H3 118.8 . . ?
C2 C3 H3 118.8 . . ?
N1 C4 C5 122.2(9) . . ?
N1 C4 H4 118.9 . . ?
C5 C4 H4 118.9 . . ?
C4 C5 C1 118.5(10) . . ?
C4 C5 C6 116.5(9) . . ?
C1 C5 C6 125.0(10) . . ?
O1 C6 N2 123.4(10) . . ?
O1 C6 C5 118.9(10) . . ?
N2 C6 C5 117.7(8) . . ?
C8 C7 N2 122.3(10) . . ?
C8 C7 C12 118.4(11) . . ?
N2 C7 C12 119.2(10) . . ?
C7 C8 C9 118.9(12) . . ?
C7 C8 H8 120.5 . . ?
C9 C8 H8 120.5 . . ?
C10 C9 C8 122.1(11) . . ?
C10 C9 Br1 119.6(10) . . ?
C8 C9 Br1 118.3(9) . . ?
C9 C10 C11 118.2(12) . . ?
C9 C10 H10 120.9 . . ?
C11 C10 H10 120.9 . . ?
C12 C11 C10 122.0(13) . . ?
C12 C11 H11 119.0 . . ?
C10 C11 H11 119.0 . . ?
C11 C12 C7 120.3(12) . . ?
C11 C12 H12 119.9 . . ?
C7 C12 H12 119.9 . . ?
C3 N1 C4 118.6(10) . . ?
C3 N1 Hg1 118.2(8) . . ?
C4 N1 Hg1 123.2(7) . . ?
C6 N2 C7 124.5(8) . . ?
C6 N2 H2B 117.7 . . ?
C7 N2 H2B 117.7 . . ?
N1 Hg1 I1 107.6(2) . . ?
N1 Hg1 I2 102.9(2) . . ?
I1 Hg1 I2 148.48(4) . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C5 C1 C2 C3 -0.7(17) . . . . ?
C1 C2 C3 N1 -0.8(19) . . . . ?
N1 C4 C5 C1 0.8(16) . . . . ?
N1 C4 C5 C6 178.8(10) . . . . ?
C2 C1 C5 C4 0.7(16) . . . . ?
C2 C1 C5 C6 -177.1(10) . . . . ?
C4 C5 C6 O1 -30.3(15) . . . . ?
C1 C5 C6 O1 147.5(12) . . . . ?
C4 C5 C6 N2 149.5(10) . . . . ?
C1 C5 C6 N2 -32.7(16) . . . . ?
N2 C7 C8 C9 -178.5(9) . . . . ?
C12 C7 C8 C9 5.0(15) . . . . ?
C7 C8 C9 C10 -4.3(16) . . . . ?
C7 C8 C9 Br1 175.8(7) . . . . ?
C8 C9 C10 C11 1.7(18) . . . . ?
Br1 C9 C10 C11 -178.4(9) . . . . ?
C9 C10 C11 C12 0(2) . . . . ?
C10 C11 C12 C7 1(2) . . . . ?
C8 C7 C12 C11 -3.5(17) . . . . ?
N2 C7 C12 C11 180.0(11) . . . . ?
C2 C3 N1 C4 2.2(18) . . . . ?
C2 C3 N1 Hg1 -177.2(9) . . . . ?
C5 C4 N1 C3 -2.3(16) . . . . ?
C5 C4 N1 Hg1 177.1(8) . . . . ?
O1 C6 N2 C7 0.8(18) . . . . ?
C5 C6 N2 C7 -179.0(10) . . . . ?
C8 C7 N2 C6 38.8(16) . . . . ?
C12 C7 N2 C6 -144.8(11) . . . . ?
C3 N1 Hg1 I1 163.7(8) . . . . ?
C4 N1 Hg1 I1 -15.7(9) . . . . ?
C3 N1 Hg1 I2 -24.6(9) . . . . ?
C4 N1 Hg1 I2 156.0(8) . . . . ?

_diffrn_measured_fraction_theta_max 1.000
_diffrn_reflns_theta_full        26.00
_diffrn_measured_fraction_theta_full 1.000
_refine_diff_density_max         1.614
_refine_diff_density_min         -1.248
_refine_diff_density_rms         0.347
_database_code_depnum_ccdc_archive 'CCDC 991770'
#######################################################################
#
#                 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_d:\determination\solution\b22\khb22

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C24 H18 Br2 Hg1 I2 N4 O2'
_chemical_formula_weight         1008.61

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'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Hg Hg -2.3894 9.2266 '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'
I I -0.4742 1.8119 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_symmetry_cell_setting           Monoclinic
_symmetry_space_group_name_H-M   C2/c

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

_cell_length_a                   24.3489(18)
_cell_length_b                   4.9200(6)
_cell_length_c                   28.395(2)
_cell_angle_alpha                90.00
_cell_angle_beta                 125.751(4)
_cell_angle_gamma                90.00
_cell_volume                     2760.6(4)
_cell_formula_units_Z            4
_cell_measurement_temperature    294(2)
_cell_measurement_reflns_used    8287
_cell_measurement_theta_min      1.77
_cell_measurement_theta_max      28.00

_exptl_crystal_description       Needle
_exptl_crystal_colour            Colorless
_exptl_crystal_size_max          0.31
_exptl_crystal_size_mid          0.07
_exptl_crystal_size_min          0.06
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    2.427
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1848
_exptl_absorpt_coefficient_mu    10.735
_exptl_absorpt_correction_type   numerical
_exptl_absorpt_correction_T_min  0.4021
_exptl_absorpt_correction_T_max  0.5248
_exptl_absorpt_process_details   'shape of crystal determined optically'

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      298(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'STOE IPDS II'
_diffrn_measurement_method       'rotation method'
_diffrn_detector_area_resol_mean '0.15 mm'
_diffrn_standards_number         0
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            8287
_diffrn_reflns_av_R_equivalents  0.1053
_diffrn_reflns_av_sigmaI/netI    0.0881
_diffrn_reflns_limit_h_min       -25
_diffrn_reflns_limit_h_max       32
_diffrn_reflns_limit_k_min       -6
_diffrn_reflns_limit_k_max       6
_diffrn_reflns_limit_l_min       -37
_diffrn_reflns_limit_l_max       37
_diffrn_reflns_theta_min         1.77
_diffrn_reflns_theta_max         28.00
_reflns_number_total             3335
_reflns_number_gt                2204
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'X-Area 1.31 (Stoe & Cie GmbH, 2005)'
_computing_cell_refinement       'X-Area 1.31 (Stoe & Cie GmbH, 2005)'
_computing_data_reduction        'X-Area 1.31 (Stoe & Cie GmbH, 2005)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    'ORTEP-3 for Windows (Farrugia, 1997)'
_computing_publication_material  'WinGX (Farrugia, 1999)'

_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. 
;

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0656P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         3335
_refine_ls_number_parameters     159
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0772
_refine_ls_R_factor_gt           0.0489
_refine_ls_wR_factor_ref         0.1280
_refine_ls_wR_factor_gt          0.1203
_refine_ls_goodness_of_fit_ref   0.885
_refine_ls_restrained_S_all      0.885
_refine_ls_shift/su_max          0.005
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C -0.1893(5) 0.704(2) 0.1076(4) 0.055(3) Uani 1 1 d . . .
H1 H -0.2199 0.8394 0.0838 0.066 Uiso 1 1 calc R . .
C2 C -0.1834(5) 0.623(2) 0.1568(4) 0.057(2) Uani 1 1 d . . .
H2 H -0.2101 0.7007 0.1668 0.068 Uiso 1 1 calc R . .
C3 C -0.1375(5) 0.426(2) 0.1906(4) 0.050(2) Uani 1 1 d . . .
H3 H -0.1345 0.3688 0.2232 0.060 Uiso 1 1 calc R . .
C4 C -0.1044(4) 0.3862(19) 0.1316(3) 0.0408(18) Uani 1 1 d . . .
H4 H -0.0777 0.3015 0.1224 0.049 Uiso 1 1 calc R . .
C5 C -0.1488(4) 0.5812(17) 0.0941(3) 0.0397(19) Uani 1 1 d . . .
C6 C -0.1518(4) 0.6726(16) 0.0431(3) 0.045(2) Uani 1 1 d . . .
C7 C -0.1290(5) 0.5278(19) -0.0274(4) 0.050(2) Uani 1 1 d . . .
C8 C -0.1662(5) 0.384(2) -0.0786(4) 0.050(2) Uani 1 1 d . . .
H8 H -0.1969 0.2520 -0.0843 0.060 Uiso 1 1 calc R . .
C9 C -0.1575(5) 0.438(2) -0.1211(4) 0.058(3) Uani 1 1 d . . .
C10 C -0.1113(7) 0.626(3) -0.1130(6) 0.082(4) Uani 1 1 d . . .
H10 H -0.1047 0.6571 -0.1417 0.098 Uiso 1 1 calc R . .
C11 C -0.0751(9) 0.769(4) -0.0620(7) 0.109(6) Uani 1 1 d . . .
H11 H -0.0444 0.8999 -0.0566 0.131 Uiso 1 1 calc R . .
C12 C -0.0833(6) 0.722(3) -0.0187(5) 0.077(4) Uani 1 1 d . . .
H12 H -0.0584 0.8193 0.0159 0.092 Uiso 1 1 calc R . .
N1 N -0.0964(4) 0.3091(15) 0.1796(3) 0.0445(17) Uani 1 1 d . . .
N2 N -0.1386(4) 0.4736(15) 0.0164(3) 0.0491(19) Uani 1 1 d . . .
H2B H -0.1361 0.3076 0.0270 0.059 Uiso 1 1 calc R . .
O1 O -0.1618(4) 0.9120(13) 0.0277(3) 0.062(2) Uani 1 1 d . . .
Hg1 Hg 0.0000 0.00209(11) 0.2500 0.04390(16) Uani 1 2 d S . .
Br1 Br -0.20955(7) 0.2491(4) -0.19244(5) 0.0875(4) Uani 1 1 d . . .
I1 I 0.03762(3) -0.12066(15) 0.18197(3) 0.0546(2) Uani 1 1 d . . .

loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_23
_atom_site_aniso_U_13
_atom_site_aniso_U_12
C1 0.056(5) 0.038(5) 0.047(5) 0.003(4) 0.017(4) 0.002(4)
C2 0.053(5) 0.063(7) 0.053(5) 0.005(5) 0.031(4) 0.006(5)
C3 0.052(5) 0.051(6) 0.041(5) 0.001(4) 0.024(4) -0.003(4)
C4 0.050(5) 0.036(4) 0.038(4) -0.004(3) 0.026(4) 0.001(4)
C5 0.047(4) 0.029(4) 0.034(4) -0.001(3) 0.019(3) 0.000(4)
C6 0.053(5) 0.023(4) 0.039(4) 0.001(3) 0.016(4) -0.001(4)
C7 0.062(5) 0.036(5) 0.051(5) 0.012(4) 0.031(4) 0.004(4)
C8 0.062(6) 0.037(5) 0.056(5) 0.001(4) 0.038(5) -0.002(5)
C9 0.065(6) 0.061(7) 0.050(5) 0.014(4) 0.035(5) 0.014(5)
C10 0.117(10) 0.069(8) 0.097(9) 0.013(7) 0.083(9) -0.005(8)
C11 0.149(14) 0.100(12) 0.108(11) -0.028(9) 0.093(11) -0.071(11)
C12 0.086(8) 0.080(9) 0.074(7) -0.019(6) 0.053(6) -0.038(7)
N1 0.054(4) 0.039(4) 0.038(3) 0.000(3) 0.025(3) -0.002(3)
N2 0.078(5) 0.025(4) 0.043(4) 0.002(3) 0.034(4) 0.001(4)
O1 0.090(5) 0.023(3) 0.056(4) 0.008(3) 0.034(4) 0.005(3)
Hg1 0.0506(3) 0.0434(3) 0.0346(2) 0.000 0.02309(19) 0.000
Br1 0.0914(8) 0.1247(13) 0.0517(6) -0.0049(6) 0.0449(6) -0.0015(8)
I1 0.0645(4) 0.0565(4) 0.0485(3) -0.0008(3) 0.0362(3) 0.0064(3)

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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
C1 C2 1.379(14) . ?
C1 C5 1.388(14) . ?
C1 H1 0.9300 . ?
C2 C3 1.363(14) . ?
C2 H2 0.9300 . ?
C3 N1 1.338(12) . ?
C3 H3 0.9300 . ?
C4 N1 1.315(11) . ?
C4 C5 1.371(12) . ?
C4 H4 0.9300 . ?
C5 C6 1.476(13) . ?
C6 O1 1.231(10) . ?
C6 N2 1.386(12) . ?
C7 C12 1.374(15) . ?
C7 C8 1.378(13) . ?
C7 N2 1.419(13) . ?
C8 C9 1.366(14) . ?
C8 H8 0.9300 . ?
C9 C10 1.368(17) . ?
C9 Br1 1.891(11) . ?
C10 C11 1.368(19) . ?
C10 H10 0.9300 . ?
C11 C12 1.378(18) . ?
C11 H11 0.9300 . ?
C12 H12 0.9300 . ?
N1 Hg1 2.510(7) . ?
N2 H2B 0.8600 . ?
Hg1 N1 2.511(7) 2 ?
Hg1 I1 2.6463(7) . ?
Hg1 I1 2.6464(7) 2 ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C2 C1 C5 118.9(9) . . ?
C2 C1 H1 120.6 . . ?
C5 C1 H1 120.6 . . ?
C3 C2 C1 118.4(10) . . ?
C3 C2 H2 120.8 . . ?
C1 C2 H2 120.8 . . ?
N1 C3 C2 124.1(10) . . ?
N1 C3 H3 118.0 . . ?
C2 C3 H3 118.0 . . ?
N1 C4 C5 125.4(9) . . ?
N1 C4 H4 117.3 . . ?
C5 C4 H4 117.3 . . ?
C4 C5 C1 117.2(8) . . ?
C4 C5 C6 122.6(8) . . ?
C1 C5 C6 120.1(8) . . ?
O1 C6 N2 122.8(9) . . ?
O1 C6 C5 121.8(9) . . ?
N2 C6 C5 115.3(7) . . ?
C12 C7 C8 120.7(10) . . ?
C12 C7 N2 120.2(9) . . ?
C8 C7 N2 119.1(9) . . ?
C9 C8 C7 119.1(10) . . ?
C9 C8 H8 120.4 . . ?
C7 C8 H8 120.4 . . ?
C8 C9 C10 121.3(10) . . ?
C8 C9 Br1 119.8(8) . . ?
C10 C9 Br1 118.9(9) . . ?
C9 C10 C11 118.8(11) . . ?
C9 C10 H10 120.6 . . ?
C11 C10 H10 120.6 . . ?
C10 C11 C12 121.3(13) . . ?
C10 C11 H11 119.4 . . ?
C12 C11 H11 119.4 . . ?
C7 C12 C11 118.7(11) . . ?
C7 C12 H12 120.6 . . ?
C11 C12 H12 120.6 . . ?
C4 N1 C3 116.0(8) . . ?
C4 N1 Hg1 120.2(6) . . ?
C3 N1 Hg1 123.4(6) . . ?
C6 N2 C7 123.8(7) . . ?
C6 N2 H2B 118.1 . . ?
C7 N2 H2B 118.1 . . ?
N1 Hg1 N1 106.0(3) . 2 ?
N1 Hg1 I1 96.74(17) . . ?
N1 Hg1 I1 99.05(18) 2 . ?
N1 Hg1 I1 99.05(18) . 2 ?
N1 Hg1 I1 96.74(17) 2 2 ?
I1 Hg1 I1 153.62(4) . 2 ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C5 C1 C2 C3 0.5(15) . . . . ?
C1 C2 C3 N1 1.5(16) . . . . ?
N1 C4 C5 C1 -1.0(13) . . . . ?
N1 C4 C5 C6 175.4(8) . . . . ?
C2 C1 C5 C4 -0.8(13) . . . . ?
C2 C1 C5 C6 -177.3(9) . . . . ?
C4 C5 C6 O1 -142.0(10) . . . . ?
C1 C5 C6 O1 34.2(13) . . . . ?
C4 C5 C6 N2 34.2(12) . . . . ?
C1 C5 C6 N2 -149.5(8) . . . . ?
C12 C7 C8 C9 -0.5(16) . . . . ?
N2 C7 C8 C9 179.4(9) . . . . ?
C7 C8 C9 C10 1.8(16) . . . . ?
C7 C8 C9 Br1 -178.5(7) . . . . ?
C8 C9 C10 C11 -2(2) . . . . ?
Br1 C9 C10 C11 178.1(13) . . . . ?
C9 C10 C11 C12 1(3) . . . . ?
C8 C7 C12 C11 0(2) . . . . ?
N2 C7 C12 C11 179.8(13) . . . . ?
C10 C11 C12 C7 0(3) . . . . ?
C5 C4 N1 C3 2.8(13) . . . . ?
C5 C4 N1 Hg1 -170.5(7) . . . . ?
C2 C3 N1 C4 -3.1(14) . . . . ?
C2 C3 N1 Hg1 169.9(8) . . . . ?
O1 C6 N2 C7 6.1(15) . . . . ?
C5 C6 N2 C7 -170.2(8) . . . . ?
C12 C7 N2 C6 51.5(14) . . . . ?
C8 C7 N2 C6 -128.3(10) . . . . ?
C4 N1 Hg1 N1 91.1(7) . . . 2 ?
C3 N1 Hg1 N1 -81.6(7) . . . 2 ?
C4 N1 Hg1 I1 -10.3(7) . . . . ?
C3 N1 Hg1 I1 176.9(7) . . . . ?
C4 N1 Hg1 I1 -169.1(6) . . . 2 ?
C3 N1 Hg1 I1 18.1(7) . . . 2 ?

_diffrn_measured_fraction_theta_max 0.996
_diffrn_reflns_theta_full        28.00
_diffrn_measured_fraction_theta_full 0.996
_refine_diff_density_max         1.254
_refine_diff_density_min         -1.251
_refine_diff_density_rms         0.231
_database_code_depnum_ccdc_archive 'CCDC 991771'
