# Electronic Supplementary Material (ESI) for CrystEngComm.
# This journal is © The Royal Society of Chemistry 2017

####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_3
_database_code_depnum_ccdc_archive 'CCDC 1016891'
_audit_update_record             
;
2017-02-02 deposited with the CCDC.
2017-02-08 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C44 H28 F8 Hg3 I6 N12 O4'
_chemical_formula_weight         2303.95

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'
F F 0.0171 0.0103 '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           Triclinic
_symmetry_space_group_name_H-M   P-1

loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   7.8051(9)
_cell_length_b                   13.1360(15)
_cell_length_c                   14.1342(15)
_cell_angle_alpha                78.497(9)
_cell_angle_beta                 85.326(9)
_cell_angle_gamma                85.781(10)
_cell_volume                     1412.9(3)
_cell_formula_units_Z            1
_cell_measurement_temperature    298(2)
_cell_measurement_reflns_used    12427
_cell_measurement_theta_min      2.37
_cell_measurement_theta_max      27.00

_exptl_crystal_description       Prism
_exptl_crystal_colour            Colorless
_exptl_crystal_size_max          0.45
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.10
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    2.708
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1038
_exptl_absorpt_coefficient_mu    11.486
_exptl_absorpt_correction_type   numerical
_exptl_absorpt_correction_T_min  0.1012
_exptl_absorpt_correction_T_max  0.3021
_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            12427
_diffrn_reflns_av_R_equivalents  0.1001
_diffrn_reflns_av_sigmaI/netI    0.1021
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_theta_min         2.37
_diffrn_reflns_theta_max         27.00
_reflns_number_total             6115
_reflns_number_gt                5446
_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)+(0.1692P)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         6115
_refine_ls_number_parameters     349
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0953
_refine_ls_R_factor_gt           0.0875
_refine_ls_wR_factor_ref         0.1919
_refine_ls_wR_factor_gt          0.1825
_refine_ls_goodness_of_fit_ref   0.935
_refine_ls_restrained_S_all      0.935
_refine_ls_shift/su_max          0.005
_refine_ls_shift/su_mean         0.001

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 0.536(2) -0.4026(14) 0.8589(12) 0.049(4) Uani 1 1 d . . .
H1 H 0.6343 -0.4217 0.8925 0.058 Uiso 1 1 calc R . .
C2 C 0.550(2) -0.3825(14) 0.7590(12) 0.052(4) Uani 1 1 d . . .
H2 H 0.6587 -0.3881 0.7276 0.063 Uiso 1 1 calc R . .
C3 C 0.261(2) -0.3480(13) 0.7585(13) 0.049(4) Uani 1 1 d . . .
H3 H 0.1624 -0.3270 0.7255 0.059 Uiso 1 1 calc R . .
C4 C 0.248(2) -0.3700(11) 0.8558(11) 0.041(4) Uani 1 1 d . . .
C5 C 0.074(2) -0.3641(12) 0.9104(12) 0.046(4) Uani 1 1 d . . .
C6 C -0.051(2) -0.3770(12) 1.0792(11) 0.044(4) Uani 1 1 d . . .
C7 C -0.005(3) -0.4031(13) 1.1752(11) 0.053(4) Uani 1 1 d . . .
C8 C -0.130(3) -0.4039(16) 1.2537(14) 0.068(6) Uani 1 1 d . . .
H8 H -0.0993 -0.4178 1.3174 0.082 Uiso 1 1 calc R . .
C9 C -0.304(2) -0.3825(14) 1.2306(13) 0.058(5) Uani 1 1 d . . .
H9 H -0.3914 -0.3869 1.2797 0.069 Uiso 1 1 calc R . .
C10 C -0.341(2) -0.3563(14) 1.1388(15) 0.055(5) Uani 1 1 d . . .
C11 C -0.221(2) -0.3521(13) 1.0593(13) 0.050(4) Uani 1 1 d . . .
H11 H -0.2536 -0.3334 0.9961 0.060 Uiso 1 1 calc R . .
C12 C 0.740(2) -0.1135(15) 0.8298(14) 0.057(5) Uani 1 1 d . . .
H12 H 0.8504 -0.1227 0.8521 0.069 Uiso 1 1 calc R . .
C13 C 0.722(2) -0.0858(16) 0.7336(13) 0.059(5) Uani 1 1 d . . .
H13 H 0.8208 -0.0758 0.6922 0.071 Uiso 1 1 calc R . .
C14 C 0.435(2) -0.0884(14) 0.7588(12) 0.052(4) Uani 1 1 d . . .
H14 H 0.3266 -0.0823 0.7350 0.062 Uiso 1 1 calc R . .
C15 C 0.450(2) -0.1140(12) 0.8581(12) 0.048(4) Uani 1 1 d . . .
C16 C 0.289(2) -0.1268(12) 0.9213(12) 0.043(4) Uani 1 1 d . . .
C17 C 0.177(2) -0.1331(12) 1.0907(11) 0.047(4) Uani 1 1 d . . .
C18 C 0.004(2) -0.1219(13) 1.0731(13) 0.052(4) Uani 1 1 d . . .
H18 H -0.0312 -0.1139 1.0105 0.062 Uiso 1 1 calc R . .
C19 C -0.118(2) -0.1229(13) 1.1521(14) 0.056(5) Uani 1 1 d . . .
C20 C -0.075(3) -0.1384(16) 1.2418(15) 0.071(6) Uani 1 1 d . . .
H20 H -0.1592 -0.1397 1.2922 0.086 Uiso 1 1 calc R . .
C21 C 0.097(3) -0.1529(19) 1.2611(15) 0.081(7) Uani 1 1 d . . .
H21 H 0.1295 -0.1643 1.3243 0.097 Uiso 1 1 calc R . .
C38 C 0.218(3) -0.1501(14) 1.1855(12) 0.061(5) Uani 1 1 d . . .
N1 N 0.3869(17) -0.3957(11) 0.9077(9) 0.044(3) Uani 1 1 d . . .
N2 N 0.4176(16) -0.3558(11) 0.7064(9) 0.047(3) Uani 1 1 d . . .
N3 N 0.0860(16) -0.3781(10) 1.0057(9) 0.046(3) Uani 1 1 d . . .
H3A H 0.1884 -0.3890 1.0254 0.055 Uiso 1 1 calc R . .
N4 N 0.5989(17) -0.1287(12) 0.8959(10) 0.051(4) Uani 1 1 d . . .
N5 N 0.575(2) -0.0724(13) 0.6964(11) 0.064(4) Uani 1 1 d . . .
N6 N 0.3110(17) -0.1307(11) 1.0154(9) 0.048(3) Uani 1 1 d . . .
H6A H 0.4151 -0.1318 1.0316 0.057 Uiso 1 1 calc R . .
O1 O -0.0565(16) -0.3479(11) 0.8690(9) 0.061(3) Uani 1 1 d . . .
O2 O 0.1551(15) -0.1322(11) 0.8873(9) 0.059(3) Uani 1 1 d . . .
Hg1 Hg 0.46983(11) -0.32573(6) 0.52390(6) 0.0663(3) Uani 1 1 d . . .
Hg2 Hg 0.5000 0.0000 0.5000 0.0700(4) Uani 1 2 d S . .
F1 F 0.1587(13) -0.4272(10) 1.1931(8) 0.072(3) Uani 1 1 d . . .
F2 F -0.5080(15) -0.3357(10) 1.1181(10) 0.079(4) Uani 1 1 d . . .
F3 F 0.3892(17) -0.1578(12) 1.2025(9) 0.089(4) Uani 1 1 d . . .
F4 F -0.2832(16) -0.1083(10) 1.1320(11) 0.086(4) Uani 1 1 d . . .
I1 I 0.2405(2) -0.42920(11) 0.46675(12) 0.0749(5) Uani 1 1 d . . .
I2 I 0.76144(18) -0.23662(10) 0.51264(11) 0.0698(4) Uani 1 1 d . . .
I3 I 0.22056(15) -0.10555(9) 0.52969(8) 0.0530(4) Uani 1 1 d . . .


_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 N1 1.31(2) . ?
C1 C2 1.38(2) . ?
C1 H1 0.9300 . ?
C2 N2 1.31(2) . ?
C2 H2 0.9300 . ?
C3 C4 1.35(2) . ?
C3 N2 1.38(2) . ?
C3 H3 0.9300 . ?
C4 N1 1.34(2) . ?
C4 C5 1.51(2) . ?
C5 O1 1.200(19) . ?
C5 N3 1.33(2) . ?
C6 C11 1.38(2) . ?
C6 C7 1.40(2) . ?
C6 N3 1.432(19) . ?
C7 F1 1.33(2) . ?
C7 C8 1.41(2) . ?
C8 C9 1.42(3) . ?
C8 H8 0.9300 . ?
C9 C10 1.33(3) . ?
C9 H9 0.9300 . ?
C10 F2 1.36(2) . ?
C10 C11 1.40(2) . ?
C11 H11 0.9300 . ?
C12 C13 1.35(3) . ?
C12 N4 1.39(2) . ?
C12 H12 0.9300 . ?
C13 N5 1.29(2) . ?
C13 H13 0.9300 . ?
C14 N5 1.35(2) . ?
C14 C15 1.39(2) . ?
C14 H14 0.9300 . ?
C15 N4 1.30(2) . ?
C15 C16 1.48(2) . ?
C16 O2 1.20(2) . ?
C16 N6 1.35(2) . ?
C17 C38 1.37(2) . ?
C17 C18 1.39(2) . ?
C17 N6 1.427(19) . ?
C18 C19 1.40(2) . ?
C18 H18 0.9300 . ?
C19 C20 1.31(3) . ?
C19 F4 1.34(2) . ?
C20 C21 1.38(3) . ?
C20 H20 0.9300 . ?
C21 C38 1.36(3) . ?
C21 H21 0.9300 . ?
C38 F3 1.37(3) . ?
N2 Hg1 2.534(12) . ?
N3 H3A 0.8600 . ?
N6 H6A 0.8600 . ?
Hg1 I1 2.5954(18) . ?
Hg1 I2 2.6143(15) . ?
Hg2 I3 2.6304(11) . ?
Hg2 I3 2.6304(11) 2_656 ?

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
N1 C1 C2 121.8(16) . . ?
N1 C1 H1 119.1 . . ?
C2 C1 H1 119.1 . . ?
N2 C2 C1 123.0(15) . . ?
N2 C2 H2 118.5 . . ?
C1 C2 H2 118.5 . . ?
C4 C3 N2 121.6(15) . . ?
C4 C3 H3 119.2 . . ?
N2 C3 H3 119.2 . . ?
N1 C4 C3 122.1(14) . . ?
N1 C4 C5 117.8(13) . . ?
C3 C4 C5 120.1(15) . . ?
O1 C5 N3 126.2(16) . . ?
O1 C5 C4 121.5(16) . . ?
N3 C5 C4 112.3(13) . . ?
C11 C6 C7 120.4(15) . . ?
C11 C6 N3 123.3(15) . . ?
C7 C6 N3 116.4(15) . . ?
F1 C7 C6 119.5(15) . . ?
F1 C7 C8 119.2(16) . . ?
C6 C7 C8 121.3(18) . . ?
C7 C8 C9 116.8(18) . . ?
C7 C8 H8 121.6 . . ?
C9 C8 H8 121.6 . . ?
C10 C9 C8 119.6(16) . . ?
C10 C9 H9 120.2 . . ?
C8 C9 H9 120.2 . . ?
C9 C10 F2 118.8(16) . . ?
C9 C10 C11 125.1(18) . . ?
F2 C10 C11 116.1(18) . . ?
C6 C11 C10 116.6(17) . . ?
C6 C11 H11 121.7 . . ?
C10 C11 H11 121.7 . . ?
C13 C12 N4 121.5(17) . . ?
C13 C12 H12 119.3 . . ?
N4 C12 H12 119.3 . . ?
N5 C13 C12 123.4(16) . . ?
N5 C13 H13 118.3 . . ?
C12 C13 H13 118.3 . . ?
N5 C14 C15 121.4(17) . . ?
N5 C14 H14 119.3 . . ?
C15 C14 H14 119.3 . . ?
N4 C15 C14 122.3(15) . . ?
N4 C15 C16 120.2(15) . . ?
C14 C15 C16 117.5(16) . . ?
O2 C16 N6 126.1(15) . . ?
O2 C16 C15 120.2(16) . . ?
N6 C16 C15 113.7(14) . . ?
C38 C17 C18 117.3(16) . . ?
C38 C17 N6 119.8(17) . . ?
C18 C17 N6 122.8(15) . . ?
C17 C18 C19 118.3(18) . . ?
C17 C18 H18 120.9 . . ?
C19 C18 H18 120.9 . . ?
C20 C19 F4 120.5(17) . . ?
C20 C19 C18 123(2) . . ?
F4 C19 C18 116.6(19) . . ?
C19 C20 C21 119.7(18) . . ?
C19 C20 H20 120.2 . . ?
C21 C20 H20 120.2 . . ?
C38 C21 C20 119(2) . . ?
C38 C21 H21 120.7 . . ?
C20 C21 H21 120.7 . . ?
C21 C38 F3 119.6(19) . . ?
C21 C38 C17 123(2) . . ?
F3 C38 C17 117.2(16) . . ?
C1 N1 C4 116.6(14) . . ?
C2 N2 C3 114.8(14) . . ?
C2 N2 Hg1 118.2(10) . . ?
C3 N2 Hg1 126.9(11) . . ?
C5 N3 C6 127.7(14) . . ?
C5 N3 H3A 116.2 . . ?
C6 N3 H3A 116.2 . . ?
C15 N4 C12 115.0(15) . . ?
C13 N5 C14 116.4(16) . . ?
C16 N6 C17 125.7(14) . . ?
C16 N6 H6A 117.1 . . ?
C17 N6 H6A 117.1 . . ?
N2 Hg1 I1 105.1(3) . . ?
N2 Hg1 I2 97.0(3) . . ?
I1 Hg1 I2 155.83(6) . . ?
I3 Hg2 I3 180 . 2_656 ?

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
N1 C1 C2 N2 0(3) . . . . ?
N2 C3 C4 N1 3(3) . . . . ?
N2 C3 C4 C5 -177.9(14) . . . . ?
N1 C4 C5 O1 -175.3(16) . . . . ?
C3 C4 C5 O1 6(2) . . . . ?
N1 C4 C5 N3 5(2) . . . . ?
C3 C4 C5 N3 -173.8(15) . . . . ?
C11 C6 C7 F1 179.8(15) . . . . ?
N3 C6 C7 F1 0(2) . . . . ?
C11 C6 C7 C8 0(3) . . . . ?
N3 C6 C7 C8 179.5(16) . . . . ?
F1 C7 C8 C9 -177.0(17) . . . . ?
C6 C7 C8 C9 3(3) . . . . ?
C7 C8 C9 C10 -5(3) . . . . ?
C8 C9 C10 F2 -179.8(17) . . . . ?
C8 C9 C10 C11 3(3) . . . . ?
C7 C6 C11 C10 -1(2) . . . . ?
N3 C6 C11 C10 178.9(15) . . . . ?
C9 C10 C11 C6 0(3) . . . . ?
F2 C10 C11 C6 -177.3(15) . . . . ?
N4 C12 C13 N5 -1(3) . . . . ?
N5 C14 C15 N4 -3(3) . . . . ?
N5 C14 C15 C16 178.0(17) . . . . ?
N4 C15 C16 O2 -166.3(17) . . . . ?
C14 C15 C16 O2 12(2) . . . . ?
N4 C15 C16 N6 14(2) . . . . ?
C14 C15 C16 N6 -167.4(16) . . . . ?
C38 C17 C18 C19 3(2) . . . . ?
N6 C17 C18 C19 -178.5(15) . . . . ?
C17 C18 C19 C20 -3(3) . . . . ?
C17 C18 C19 F4 177.8(15) . . . . ?
F4 C19 C20 C21 -179.7(18) . . . . ?
C18 C19 C20 C21 1(3) . . . . ?
C19 C20 C21 C38 0(3) . . . . ?
C20 C21 C38 F3 176(2) . . . . ?
C20 C21 C38 C17 0(3) . . . . ?
C18 C17 C38 C21 -2(3) . . . . ?
N6 C17 C38 C21 179.6(18) . . . . ?
C18 C17 C38 F3 -177.9(15) . . . . ?
N6 C17 C38 F3 4(2) . . . . ?
C2 C1 N1 C4 1(3) . . . . ?
C3 C4 N1 C1 -3(2) . . . . ?
C5 C4 N1 C1 178.4(14) . . . . ?
C1 C2 N2 C3 1(3) . . . . ?
C1 C2 N2 Hg1 -178.8(14) . . . . ?
C4 C3 N2 C2 -2(2) . . . . ?
C4 C3 N2 Hg1 177.3(12) . . . . ?
O1 C5 N3 C6 0(3) . . . . ?
C4 C5 N3 C6 179.6(14) . . . . ?
C11 C6 N3 C5 -6(3) . . . . ?
C7 C6 N3 C5 174.5(15) . . . . ?
C14 C15 N4 C12 2(3) . . . . ?
C16 C15 N4 C12 -179.4(16) . . . . ?
C13 C12 N4 C15 0(3) . . . . ?
C12 C13 N5 C14 -1(3) . . . . ?
C15 C14 N5 C13 2(3) . . . . ?
O2 C16 N6 C17 -6(3) . . . . ?
C15 C16 N6 C17 174.0(14) . . . . ?
C38 C17 N6 C16 171.9(16) . . . . ?
C18 C17 N6 C16 -6(3) . . . . ?
C2 N2 Hg1 I1 132.1(13) . . . . ?
C3 N2 Hg1 I1 -47.4(14) . . . . ?
C2 N2 Hg1 I2 -37.9(13) . . . . ?
C3 N2 Hg1 I2 142.7(13) . . . . ?

_diffrn_measured_fraction_theta_max 0.995
_diffrn_reflns_theta_full        27.00
_diffrn_measured_fraction_theta_full 0.995
_refine_diff_density_max         1.251
_refine_diff_density_min         -1.362
_refine_diff_density_rms         0.571
####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_d:\determination\solution\c460\new-khc460-abs
_database_code_depnum_ccdc_archive 'CCDC 1016889'
_audit_update_record             
;
2014-07-29 deposited with the CCDC.
2017-02-08 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C11 H7 Cl2 F2 Hg1 N3 O1'
_chemical_formula_weight         506.69

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'
Cl Cl 0.1484 0.1585 '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'

_symmetry_cell_setting           Monoclinic
_symmetry_space_group_name_H-M   P21/c

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

_cell_length_a                   10.988(3)
_cell_length_b                   3.9173(9)
_cell_length_c                   31.538(9)
_cell_angle_alpha                90.00
_cell_angle_beta                 99.68(2)
_cell_angle_gamma                90.00
_cell_volume                     1338.2(6)
_cell_formula_units_Z            4
_cell_measurement_temperature    298(2)
_cell_measurement_reflns_used    10530
_cell_measurement_theta_min      2.47
_cell_measurement_theta_max      27.00

_exptl_crystal_description       Needle
_exptl_crystal_colour            Colorless
_exptl_crystal_size_max          0.20
_exptl_crystal_size_mid          0.07
_exptl_crystal_size_min          0.05
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    2.515
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             936
_exptl_absorpt_coefficient_mu    11.921
_exptl_absorpt_correction_type   numerical
_exptl_absorpt_correction_T_min  0.1381
_exptl_absorpt_correction_T_max  0.2611
_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            10530
_diffrn_reflns_av_R_equivalents  0.0889
_diffrn_reflns_av_sigmaI/netI    0.1025
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_k_min       -5
_diffrn_reflns_limit_k_max       5
_diffrn_reflns_limit_l_min       -38
_diffrn_reflns_limit_l_max       40
_diffrn_reflns_theta_min         2.47
_diffrn_reflns_theta_max         27.00
_reflns_number_total             2882
_reflns_number_gt                2520
_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)+(0.0557P)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         2882
_refine_ls_number_parameters     176
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0965
_refine_ls_R_factor_gt           0.0941
_refine_ls_wR_factor_ref         0.1981
_refine_ls_wR_factor_gt          0.1497
_refine_ls_goodness_of_fit_ref   0.968
_refine_ls_restrained_S_all      0.968
_refine_ls_shift/su_max          0.003
_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 0.452(2) 1.243(7) 0.1425(7) 0.038(6) Uani 1 1 d . . .
H1 H 0.5290 1.3475 0.1474 0.046 Uiso 1 1 calc R . .
C2 C 0.396(2) 1.170(7) 0.1764(8) 0.046(8) Uani 1 1 d . . .
H2 H 0.4354 1.2351 0.2036 0.055 Uiso 1 1 calc R . .
C3 C 0.238(2) 0.915(6) 0.1324(7) 0.042(5) Uani 1 1 d . . .
H3 H 0.1650 0.7927 0.1273 0.039 Uiso 1 1 calc R . .
C4 C 0.297(2) 1.001(5) 0.1009(9) 0.038(6) Uani 1 1 d . . .
C5 C 0.234(2) 0.908(7) 0.0563(9) 0.045(6) Uani 1 1 d . . .
C6 C 0.250(3) 0.983(6) -0.0236(9) 0.050(8) Uani 1 1 d . . .
C7 C 0.323(3) 1.120(6) -0.0500(11) 0.053(9) Uani 1 1 d . . .
C8 C 0.297(3) 1.125(8) -0.0938(9) 0.057(9) Uani 1 1 d . . .
H8 H 0.3504 1.2177 -0.1108 0.068 Uiso 1 1 calc R . .
C9 C 0.187(3) 0.983(6) -0.1104(9) 0.048(7) Uani 1 1 d . . .
H9 H 0.1627 0.9862 -0.1401 0.058 Uiso 1 1 calc R . .
C10 C 0.109(3) 0.833(7) -0.0856(10) 0.047(7) Uani 1 1 d . . .
C11 C 0.135(2) 0.837(7) -0.0418(11) 0.049(7) Uani 1 1 d . . .
H11 H 0.0805 0.7507 -0.0249 0.059 Uiso 1 1 calc R . .
N1 N 0.3978(18) 1.167(5) 0.1010(7) 0.040(5) Uani 1 1 d . . .
N2 N 0.2910(16) 1.017(6) 0.1736(6) 0.043(5) Uani 1 1 d . . .
N3 N 0.288(2) 1.007(5) 0.0204(8) 0.044(7) Uani 1 1 d . . .
H3A H 0.3593 1.1018 0.0275 0.067 Uiso 1 1 calc R . .
O1 O 0.136(2) 0.735(5) 0.0467(7) 0.071(7) Uani 1 1 d . . .
Hg1 Hg 0.17845(10) 0.9422(2) 0.23678(4) 0.0417(3) Uani 1 1 d . . .
Cl1 Cl 0.0328(6) 0.5590(18) 0.2013(2) 0.0455(15) Uani 1 1 d . . .
Cl2 Cl 0.3170(7) 1.2792(18) 0.2823(3) 0.0537(18) Uani 1 1 d . . .
F1 F 0.4322(15) 1.261(4) -0.0315(5) 0.061(5) Uani 1 1 d . . .
F2 F -0.0056(16) 0.709(4) -0.1071(5) 0.067(5) Uani 1 1 d . . .


_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 1.35(3) . ?
C1 N1 1.38(3) . ?
C1 H1 0.9300 . ?
C2 N2 1.29(3) . ?
C2 H2 0.9300 . ?
C3 C4 1.32(3) . ?
C3 N2 1.39(3) . ?
C3 H3 0.9300 . ?
C4 N1 1.28(3) . ?
C4 C5 1.51(4) . ?
C5 O1 1.27(3) . ?
C5 N3 1.42(3) . ?
C6 C7 1.36(3) . ?
C6 N3 1.38(4) . ?
C6 C11 1.42(4) . ?
C7 F1 1.36(3) . ?
C7 C8 1.36(4) . ?
C8 C9 1.35(4) . ?
C8 H8 0.9300 . ?
C9 C10 1.39(4) . ?
C9 H9 0.9300 . ?
C10 C11 1.36(4) . ?
C10 F2 1.41(3) . ?
C11 H11 0.9300 . ?
N2 Hg1 2.532(17) . ?
N3 H3A 0.8600 . ?
Hg1 Cl2 2.321(7) . ?
Hg1 Cl1 2.337(7) . ?

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 N1 122(2) . . ?
C2 C1 H1 119.2 . . ?
N1 C1 H1 119.2 . . ?
N2 C2 C1 125(2) . . ?
N2 C2 H2 117.7 . . ?
C1 C2 H2 117.7 . . ?
C4 C3 N2 117(2) . . ?
C4 C3 H3 121.5 . . ?
N2 C3 H3 121.5 . . ?
N1 C4 C3 131(3) . . ?
N1 C4 C5 113(2) . . ?
C3 C4 C5 116(2) . . ?
O1 C5 N3 114(3) . . ?
O1 C5 C4 127(2) . . ?
N3 C5 C4 119(2) . . ?
C7 C6 N3 119(3) . . ?
C7 C6 C11 119(3) . . ?
N3 C6 C11 122(2) . . ?
F1 C7 C6 118(3) . . ?
F1 C7 C8 117(2) . . ?
C6 C7 C8 125(3) . . ?
C9 C8 C7 114(3) . . ?
C9 C8 H8 122.9 . . ?
C7 C8 H8 122.9 . . ?
C8 C9 C10 124(3) . . ?
C8 C9 H9 118.2 . . ?
C10 C9 H9 118.2 . . ?
C11 C10 C9 121(3) . . ?
C11 C10 F2 121(3) . . ?
C9 C10 F2 118(3) . . ?
C10 C11 C6 116(3) . . ?
C10 C11 H11 122.1 . . ?
C6 C11 H11 122.1 . . ?
C4 N1 C1 110(2) . . ?
C2 N2 C3 115(2) . . ?
C2 N2 Hg1 123.4(16) . . ?
C3 N2 Hg1 121.5(14) . . ?
C6 N3 C5 133(2) . . ?
C6 N3 H3A 113.4 . . ?
C5 N3 H3A 113.4 . . ?
Cl2 Hg1 Cl1 170.6(2) . . ?
Cl2 Hg1 N2 93.7(5) . . ?
Cl1 Hg1 N2 94.8(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
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
N1 C1 C2 N2 2(4) . . . . ?
N2 C3 C4 N1 0(4) . . . . ?
N2 C3 C4 C5 -176(2) . . . . ?
N1 C4 C5 O1 177(3) . . . . ?
C3 C4 C5 O1 -6(4) . . . . ?
N1 C4 C5 N3 0(3) . . . . ?
C3 C4 C5 N3 177(2) . . . . ?
N3 C6 C7 F1 3(3) . . . . ?
C11 C6 C7 F1 179(2) . . . . ?
N3 C6 C7 C8 -178(2) . . . . ?
C11 C6 C7 C8 -2(4) . . . . ?
F1 C7 C8 C9 -180(2) . . . . ?
C6 C7 C8 C9 1(4) . . . . ?
C7 C8 C9 C10 -2(4) . . . . ?
C8 C9 C10 C11 4(4) . . . . ?
C8 C9 C10 F2 177(2) . . . . ?
C9 C10 C11 C6 -4(4) . . . . ?
F2 C10 C11 C6 -177(2) . . . . ?
C7 C6 C11 C10 3(4) . . . . ?
N3 C6 C11 C10 179(2) . . . . ?
C3 C4 N1 C1 4(4) . . . . ?
C5 C4 N1 C1 -180(2) . . . . ?
C2 C1 N1 C4 -5(4) . . . . ?
C1 C2 N2 C3 2(4) . . . . ?
C1 C2 N2 Hg1 -173(2) . . . . ?
C4 C3 N2 C2 -3(3) . . . . ?
C4 C3 N2 Hg1 172.1(16) . . . . ?
C7 C6 N3 C5 177(2) . . . . ?
C11 C6 N3 C5 1(4) . . . . ?
O1 C5 N3 C6 8(4) . . . . ?
C4 C5 N3 C6 -175(2) . . . . ?
C2 N2 Hg1 Cl2 6(2) . . . . ?
C3 N2 Hg1 Cl2 -168.5(18) . . . . ?
C2 N2 Hg1 Cl1 -169(2) . . . . ?
C3 N2 Hg1 Cl1 15.6(19) . . . . ?

_diffrn_measured_fraction_theta_max 0.997
_diffrn_reflns_theta_full        27.00
_diffrn_measured_fraction_theta_full 0.997
_refine_diff_density_max         1.251
_refine_diff_density_min         -1.258
_refine_diff_density_rms         0.336
####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_d:\determination\solution\914\new
_database_code_depnum_ccdc_archive 'CCDC 1016885'
_audit_update_record             
;
2014-07-29 deposited with the CCDC.
2017-02-08 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C11 H7 Br2 F2 Hg1 N3 O1'
_chemical_formula_weight         595.59

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'
F F 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_symmetry_cell_setting           Orthorhombic
_symmetry_space_group_name_H-M   Pbca

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

_cell_length_a                   6.7713(12)
_cell_length_b                   12.7185(15)
_cell_length_c                   33.489(4)
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_volume                     2884.1(7)
_cell_formula_units_Z            8
_cell_measurement_temperature    298(2)
_cell_measurement_reflns_used    15548
_cell_measurement_theta_min      2.43
_cell_measurement_theta_max      27.00

_exptl_crystal_description       Needle
_exptl_crystal_colour            Colorless
_exptl_crystal_size_max          0.38
_exptl_crystal_size_mid          0.08
_exptl_crystal_size_min          0.07
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    2.746
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             2160
_exptl_absorpt_coefficient_mu    16.234
_exptl_absorpt_correction_type   numerical
_exptl_absorpt_correction_T_min  0.7521
_exptl_absorpt_correction_T_max  0.8561
_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            15548
_diffrn_reflns_av_R_equivalents  0.1020
_diffrn_reflns_av_sigmaI/netI    0.1398
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_l_min       -42
_diffrn_reflns_limit_l_max       37
_diffrn_reflns_theta_min         2.43
_diffrn_reflns_theta_max         27.00
_reflns_number_total             3150
_reflns_number_gt                1646
_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)+(0.0791P)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         3150
_refine_ls_number_parameters     181
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0998
_refine_ls_R_factor_gt           0.0928
_refine_ls_wR_factor_ref         0.1996
_refine_ls_wR_factor_gt          0.1944
_refine_ls_goodness_of_fit_ref   1.032
_refine_ls_restrained_S_all      1.032
_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 0.442(3) 0.0368(18) 0.1072(8) 0.062(6) Uani 1 1 d . . .
H1 H 0.4484 -0.0356 0.1036 0.074 Uiso 1 1 calc R . .
C2 C 0.471(3) 0.101(2) 0.0741(6) 0.057(5) Uani 1 1 d . . .
H2 H 0.4961 0.0719 0.0492 0.068 Uiso 1 1 calc R . .
C3 C 0.436(2) 0.2410(16) 0.1151(6) 0.048(5) Uani 1 1 d . . .
H3 H 0.4366 0.3133 0.1194 0.058 Uiso 1 1 calc R . .
C4 C 0.407(3) 0.1746(17) 0.1478(6) 0.046(4) Uani 1 1 d . . .
C5 C 0.383(2) 0.2206(14) 0.1890(6) 0.039(4) Uani 1 1 d . . .
C6 C 0.378(2) 0.1554(14) 0.2584(6) 0.040(4) Uani 1 1 d . . .
C7 C 0.385(3) 0.061(2) 0.2803(7) 0.060(6) Uani 1 1 d . . .
C8 C 0.400(3) 0.064(2) 0.3213(7) 0.064(7) Uani 1 1 d . . .
H8 H 0.4141 0.0015 0.3356 0.077 Uiso 1 1 calc R . .
C9 C 0.395(3) 0.160(2) 0.3416(7) 0.059(6) Uani 1 1 d . . .
H9 H 0.3928 0.1615 0.3693 0.070 Uiso 1 1 calc R . .
C10 C 0.392(3) 0.251(2) 0.3202(8) 0.065(7) Uani 1 1 d . . .
C11 C 0.381(3) 0.2490(18) 0.2793(6) 0.051(5) Uani 1 1 d . . .
H11 H 0.3754 0.3121 0.2653 0.062 Uiso 1 1 calc R . .
N1 N 0.408(2) 0.0721(15) 0.1423(6) 0.054(4) Uani 1 1 d . . .
N2 N 0.461(2) 0.2057(15) 0.0787(5) 0.053(4) Uani 1 1 d . . .
N3 N 0.376(2) 0.1448(13) 0.2172(5) 0.046(4) Uani 1 1 d . . .
H3A H 0.3700 0.0814 0.2084 0.055 Uiso 1 1 calc R . .
O1 O 0.380(2) 0.3147(11) 0.1952(5) 0.059(4) Uani 1 1 d . . .
Hg1 Hg 0.51783(11) 0.32955(7) 0.02257(2) 0.0551(3) Uani 1 1 d . . .
Br1 Br 0.5368(3) 0.49387(19) 0.05950(7) 0.0647(7) Uani 1 1 d . . .
Br2 Br 0.5070(3) 0.1975(2) -0.03102(7) 0.0646(6) Uani 1 1 d . . .
F1 F 0.380(2) -0.0278(9) 0.2604(4) 0.065(3) Uani 1 1 d . . .
F2 F 0.390(3) 0.3421(12) 0.3401(4) 0.084(4) Uani 1 1 d . . .


_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 N1 1.28(3) . ?
C1 C2 1.39(3) . ?
C1 H1 0.9300 . ?
C2 N2 1.34(3) . ?
C2 H2 0.9300 . ?
C3 N2 1.31(3) . ?
C3 C4 1.39(3) . ?
C3 H3 0.9300 . ?
C4 N1 1.32(3) . ?
C4 C5 1.51(3) . ?
C5 O1 1.21(2) . ?
C5 N3 1.35(2) . ?
C6 C11 1.38(3) . ?
C6 N3 1.39(3) . ?
C6 C7 1.41(3) . ?
C7 F1 1.31(3) . ?
C7 C8 1.38(3) . ?
C8 C9 1.40(3) . ?
C8 H8 0.9300 . ?
C9 C10 1.36(3) . ?
C9 H9 0.9300 . ?
C10 F2 1.34(3) . ?
C10 C11 1.37(3) . ?
C11 H11 0.9300 . ?
N2 Hg1 2.483(18) . ?
N3 H3A 0.8600 . ?
Hg1 Br1 2.432(2) . ?
Hg1 Br2 2.458(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
N1 C1 C2 123(2) . . ?
N1 C1 H1 118.3 . . ?
C2 C1 H1 118.3 . . ?
N2 C2 C1 119.0(19) . . ?
N2 C2 H2 120.5 . . ?
C1 C2 H2 120.5 . . ?
N2 C3 C4 123(2) . . ?
N2 C3 H3 118.7 . . ?
C4 C3 H3 118.7 . . ?
N1 C4 C3 119.4(19) . . ?
N1 C4 C5 120.8(18) . . ?
C3 C4 C5 119.8(19) . . ?
O1 C5 N3 125.6(19) . . ?
O1 C5 C4 122.7(18) . . ?
N3 C5 C4 111.5(16) . . ?
C11 C6 N3 126.0(18) . . ?
C11 C6 C7 118.0(18) . . ?
N3 C6 C7 116.0(18) . . ?
F1 C7 C8 122(2) . . ?
F1 C7 C6 118(2) . . ?
C8 C7 C6 120(2) . . ?
C7 C8 C9 120(2) . . ?
C7 C8 H8 119.8 . . ?
C9 C8 H8 119.8 . . ?
C10 C9 C8 119(2) . . ?
C10 C9 H9 120.4 . . ?
C8 C9 H9 120.4 . . ?
F2 C10 C9 118(2) . . ?
F2 C10 C11 121(2) . . ?
C9 C10 C11 121(2) . . ?
C10 C11 C6 121(2) . . ?
C10 C11 H11 119.3 . . ?
C6 C11 H11 119.3 . . ?
C1 N1 C4 118(2) . . ?
C3 N2 C2 116.9(19) . . ?
C3 N2 Hg1 120.5(15) . . ?
C2 N2 Hg1 122.3(14) . . ?
C5 N3 C6 128.8(17) . . ?
C5 N3 H3A 115.6 . . ?
C6 N3 H3A 115.6 . . ?
Br1 Hg1 Br2 163.67(10) . . ?
Br1 Hg1 N2 99.7(4) . . ?
Br2 Hg1 N2 96.6(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
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
N1 C1 C2 N2 -1(3) . . . . ?
N2 C3 C4 N1 1(3) . . . . ?
N2 C3 C4 C5 179.1(16) . . . . ?
N1 C4 C5 O1 -179.8(18) . . . . ?
C3 C4 C5 O1 2(3) . . . . ?
N1 C4 C5 N3 4(2) . . . . ?
C3 C4 C5 N3 -174.0(15) . . . . ?
C11 C6 C7 F1 179.2(18) . . . . ?
N3 C6 C7 F1 -3(3) . . . . ?
C11 C6 C7 C8 -2(3) . . . . ?
N3 C6 C7 C8 175.9(17) . . . . ?
F1 C7 C8 C9 -176.6(19) . . . . ?
C6 C7 C8 C9 5(3) . . . . ?
C7 C8 C9 C10 -6(3) . . . . ?
C8 C9 C10 F2 -179(2) . . . . ?
C8 C9 C10 C11 4(3) . . . . ?
F2 C10 C11 C6 -178.5(19) . . . . ?
C9 C10 C11 C6 -2(3) . . . . ?
N3 C6 C11 C10 -177.1(18) . . . . ?
C7 C6 C11 C10 0(3) . . . . ?
C2 C1 N1 C4 -3(3) . . . . ?
C3 C4 N1 C1 2(3) . . . . ?
C5 C4 N1 C1 -175.7(18) . . . . ?
C4 C3 N2 C2 -4(3) . . . . ?
C4 C3 N2 Hg1 -178.5(13) . . . . ?
C1 C2 N2 C3 4(3) . . . . ?
C1 C2 N2 Hg1 178.2(14) . . . . ?
O1 C5 N3 C6 -4(3) . . . . ?
C4 C5 N3 C6 171.6(16) . . . . ?
C11 C6 N3 C5 2(3) . . . . ?
C7 C6 N3 C5 -175.3(16) . . . . ?
C3 N2 Hg1 Br1 5.0(14) . . . . ?
C2 N2 Hg1 Br1 -169.3(15) . . . . ?
C3 N2 Hg1 Br2 -173.8(13) . . . . ?
C2 N2 Hg1 Br2 12.0(16) . . . . ?

_diffrn_measured_fraction_theta_max 0.998
_diffrn_reflns_theta_full        27.00
_diffrn_measured_fraction_theta_full 0.998
_refine_diff_density_max         1.258
_refine_diff_density_min         -1.260
_refine_diff_density_rms         0.360
