# Electronic Supplementary Material (ESI) for Dalton Transactions.
# This journal is © The Royal Society of Chemistry 2015

####################################################################### 
# 
# 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_1
_database_code_depnum_ccdc_archive 'CCDC 1034446'
_audit_update_record             
;
2015-01-29 deposited with the CCDC.
2015-02-10 downloaded from the CCDC.
;


_audit_creation_method           SHELXL-2013
_chemical_name_systematic        
;
 ?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C12 H9 Br2 F Hg N2'
_chemical_formula_sum            'C12 H9 Br2 F Hg N2'
_chemical_formula_weight         560.62

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'
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'

_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'

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

loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   3.9779(2)
_cell_length_b                   18.8497(7)
_cell_length_c                   19.0199(8)
_cell_angle_alpha                104.225(3)
_cell_angle_beta                 91.415(3)
_cell_angle_gamma                94.296(3)
_cell_volume                     1377.17(11)
_cell_formula_units_Z            4
_cell_measurement_temperature    100(1)
_cell_measurement_reflns_used    2443
_cell_measurement_theta_min      3.3390
_cell_measurement_theta_max      28.1770

_exptl_crystal_description       needle
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    2.704
_exptl_crystal_F_000             1016
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.45
_exptl_crystal_size_mid          0.07
_exptl_crystal_size_min          0.07
_exptl_absorpt_coefficient_mu    16.972
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_T_min  0.70206
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.33 (release 27-03-2014 CrysAlis171 .NET)
(compiled Mar 27 2014,17:12:48)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;

_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      100(1)
_diffrn_radiation_wavelength     0.7107
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_source         'Enhance (Mo) X-ray Source'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Xcalibur, Eos'
_diffrn_detector_area_resol_mean 16.1544
_diffrn_measurement_method       ω-scan
_diffrn_reflns_number            8389
_diffrn_reflns_av_unetI/netI     0.0642
_diffrn_reflns_av_R_equivalents  0.0499
_diffrn_reflns_limit_h_min       -4
_diffrn_reflns_limit_h_max       4
_diffrn_reflns_limit_k_min       -22
_diffrn_reflns_limit_k_max       21
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_theta_min         3.228
_diffrn_reflns_theta_max         24.999
_diffrn_reflns_theta_full        25.000
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measured_fraction_theta_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_point_group_measured_fraction_full 0.997
_reflns_number_total             4843
_reflns_number_gt                4108
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_reflns_special_details          
;
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;

_computing_data_collection       'CrysAlis Pro (Agilent Technologies (2011))'
_computing_cell_refinement       'CrysAlis Pro (Agilent Technologies (2011))'
_computing_data_reduction        'CrysAlis Pro (Agilent Technologies (2011))'
_computing_structure_solution    'SIR92 (Altomare et al., 1993)'
_computing_structure_refinement  'SHELXL-2013 (Sheldrick, 2013)'
_computing_molecular_graphics    'Mercury (MacRae et al., 2009)'
_computing_publication_material  'SHELXL-2013 (Sheldrick, 2013)'

_refine_special_details          
;
Refined as a 2-component twin.
High residual density peaks are observed close to Hg atom (around 0.9A)
Restraints for the planarity of the aromatic rings (FLAT), for the 
shape of ellipsoids (ISOR) and for similar geometry of pyridine rings (SAME)
have been applied to keep the model physically reasonable.
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0920P)²+75.4000P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         4843
_refine_ls_number_parameters     326
_refine_ls_number_restraints     204
_refine_ls_R_factor_all          0.0862
_refine_ls_R_factor_gt           0.0750
_refine_ls_wR_factor_ref         0.2258
_refine_ls_wR_factor_gt          0.2198
_refine_ls_goodness_of_fit_ref   1.260
_refine_ls_restrained_S_all      1.236
_refine_ls_shift/su_max          0.009
_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_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Hg1A Hg 1.1788(2) 0.42067(5) -0.44082(5) 0.0171(3) Uani 1 1 d . . . . .
Br1A Br 1.5460(5) 0.34066(13) -0.52315(12) 0.0172(5) Uani 1 1 d . . . . .
Br2A Br 0.8555(6) 0.52440(13) -0.38069(13) 0.0185(5) Uani 1 1 d . . . . .
N1A N 1.102(4) 0.3447(10) -0.3552(9) 0.021(4) Uani 1 1 d D U . . .
C2A C 1.208(4) 0.2772(11) -0.3716(10) 0.017(5) Uani 1 1 d D U . . .
H2A H 1.3030 0.2593 -0.4172 0.020 Uiso 1 1 calc R U . . .
C3A C 1.182(4) 0.2330(11) -0.3237(11) 0.019(5) Uani 1 1 d D U . . .
H3A H 1.2580 0.1851 -0.3362 0.023 Uiso 1 1 calc R U . . .
C4A C 1.044(4) 0.2593(11) -0.2576(11) 0.018(5) Uani 1 1 d D U . . .
C5A C 0.935(4) 0.3287(11) -0.2405(11) 0.022(5) Uani 1 1 d D U . . .
H5A H 0.8386 0.3476 -0.1952 0.026 Uiso 1 1 calc R U . . .
C6A C 0.968(4) 0.3704(12) -0.2911(11) 0.022(5) Uani 1 1 d D U . . .
H6A H 0.8934 0.4184 -0.2799 0.026 Uiso 1 1 calc R U . . .
C7A C 1.024(5) 0.2123(12) -0.2055(12) 0.012(4) Uani 1 1 d . U . . .
H7A H 1.1450 0.1698 -0.2129 0.015 Uiso 1 1 calc R U . . .
N8A N 0.835(5) 0.2301(11) -0.1488(10) 0.017(4) Uani 1 1 d . U . . .
C9A C 0.796(4) 0.1832(12) -0.1023(12) 0.015(5) Uani 1 1 d . U . . .
C10A C 0.668(4) 0.2163(14) -0.0341(13) 0.020(5) Uani 1 1 d . U . . .
H10A H 0.6062 0.2653 -0.0255 0.024 Uiso 1 1 calc R U . . .
C11A C 0.629(5) 0.1795(15) 0.0205(15) 0.030(6) Uani 1 1 d . U . . .
H11A H 0.5420 0.2020 0.0660 0.036 Uiso 1 1 calc R U . . .
C12A C 0.722(5) 0.1083(15) 0.0051(14) 0.026(6) Uani 1 1 d . U . . .
F12A F 0.674(4) 0.0699(9) 0.0559(8) 0.034(4) Uani 1 1 d . U . . .
C13A C 0.850(5) 0.0726(13) -0.0611(12) 0.018(5) Uani 1 1 d . U . . .
H13A H 0.9110 0.0236 -0.0696 0.021 Uiso 1 1 calc R U . . .
C14A C 0.885(4) 0.1129(14) -0.1148(14) 0.024(5) Uani 1 1 d . U . . .
H14A H 0.9713 0.0905 -0.1603 0.029 Uiso 1 1 calc R U . . .
Hg1B Hg 1.1744(2) 0.96625(5) -0.39622(5) 0.0163(3) Uani 1 1 d . . . . .
Br1B Br 0.7446(5) 0.90422(12) -0.49270(12) 0.0167(5) Uani 1 1 d . . . . .
Br2B Br 1.5946(5) 1.05681(12) -0.31591(12) 0.0173(5) Uani 1 1 d . . . . .
N1B N 1.185(4) 0.8740(9) -0.3274(8) 0.014(4) Uani 1 1 d D U . . .
C2B C 1.368(4) 0.8837(11) -0.2647(10) 0.017(5) Uani 1 1 d D U . . .
H2B H 1.4733 0.9312 -0.2429 0.021 Uiso 1 1 calc R U . . .
C3B C 1.412(4) 0.8285(11) -0.2304(11) 0.020(5) Uani 1 1 d D U . . .
H3B H 1.5429 0.8377 -0.1862 0.024 Uiso 1 1 calc R U . . .
C4B C 1.259(4) 0.7593(11) -0.2623(10) 0.015(5) Uani 1 1 d D U . . .
C5B C 1.070(4) 0.7485(11) -0.3263(10) 0.012(4) Uani 1 1 d D U . . .
H5B H 0.9625 0.7014 -0.3489 0.014 Uiso 1 1 calc R U . . .
C6B C 1.039(4) 0.8067(11) -0.3573(11) 0.017(5) Uani 1 1 d D U . . .
H6B H 0.9094 0.7987 -0.4015 0.021 Uiso 1 1 calc R U . . .
C7B C 1.303(6) 0.6937(14) -0.2320(13) 0.022(5) Uani 1 1 d . U . . .
H7B H 1.1600 0.6497 -0.2491 0.026 Uiso 1 1 calc R U . . .
N8B N 1.529(5) 0.6979(11) -0.1840(10) 0.018(4) Uani 1 1 d . U . . .
C9B C 1.580(4) 0.6354(13) -0.1562(11) 0.014(5) Uani 1 1 d . U . . .
C10B C 1.756(4) 0.6470(14) -0.0884(12) 0.018(5) Uani 1 1 d . U . . .
H10B H 1.8404 0.6954 -0.0637 0.022 Uiso 1 1 calc R U . . .
C11B C 1.808(4) 0.5907(13) -0.0577(12) 0.017(5) Uani 1 1 d . U . . .
H11B H 1.9270 0.5990 -0.0121 0.020 Uiso 1 1 calc R U . . .
C12B C 1.681(5) 0.5198(15) -0.0954(13) 0.024(6) Uani 1 1 d . U . . .
F12B F 1.730(4) 0.4639(8) -0.0640(9) 0.030(3) Uani 1 1 d . U . . .
C13B C 1.510(5) 0.5043(14) -0.1607(12) 0.020(5) Uani 1 1 d . U . . .
H13B H 1.4279 0.4555 -0.1845 0.024 Uiso 1 1 calc R U . . .
C14B C 1.458(4) 0.5629(13) -0.1913(12) 0.016(5) Uani 1 1 d . U . . .
H14B H 1.3387 0.5537 -0.2370 0.019 Uiso 1 1 calc R U . . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Hg1A N1A 2.429(19) . ?
Hg1A Br2A 2.477(2) . ?
Hg1A Br1A 2.478(2) . ?
Hg1A Br1A 3.023(2) 1_455 ?
Br1A Hg1A 3.023(2) 1_655 ?
N1A C6A 1.34(2) . ?
N1A C2A 1.34(2) . ?
C2A C3A 1.38(3) . ?
C3A C4A 1.38(2) . ?
C4A C5A 1.37(2) . ?
C4A C7A 1.48(3) . ?
C5A C6A 1.39(3) . ?
C7A N8A 1.32(3) . ?
N8A C9A 1.40(3) . ?
C9A C14A 1.36(3) . ?
C9A C10A 1.42(3) . ?
C10A C11A 1.39(4) . ?
C11A C12A 1.38(4) . ?
C12A F12A 1.35(3) . ?
C12A C13A 1.40(3) . ?
C13A C14A 1.42(4) . ?
Hg1B N1B 2.421(17) . ?
Hg1B Br1B 2.480(2) . ?
Hg1B Br2B 2.491(2) . ?
Hg1B Br1B 3.070(2) 1_655 ?
Br1B Hg1B 3.070(2) 1_455 ?
N1B C6B 1.34(2) . ?
N1B C2B 1.35(2) . ?
C2B C3B 1.37(3) . ?
C3B C4B 1.38(3) . ?
C4B C5B 1.38(2) . ?
C4B C7B 1.51(3) . ?
C5B C6B 1.38(3) . ?
C7B N8B 1.25(3) . ?
N8B C9B 1.43(3) . ?
C9B C14B 1.41(3) . ?
C9B C10B 1.41(3) . ?
C10B C11B 1.36(3) . ?
C11B C12B 1.40(4) . ?
C12B F12B 1.36(3) . ?
C12B C13B 1.36(4) . ?
C13B C14B 1.40(3) . ?

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
N1A Hg1A Br2A 99.2(4) . . ?
N1A Hg1A Br1A 97.0(4) . . ?
Br2A Hg1A Br1A 163.70(9) . . ?
N1A Hg1A Br1A 88.3(4) . 1_455 ?
Br2A Hg1A Br1A 90.63(7) . 1_455 ?
Br1A Hg1A Br1A 92.07(7) . 1_455 ?
Hg1A Br1A Hg1A 92.07(7) . 1_655 ?
C6A N1A C2A 119.7(18) . . ?
C6A N1A Hg1A 121.1(14) . . ?
C2A N1A Hg1A 119.2(13) . . ?
N1A C2A C3A 121.5(18) . . ?
C2A C3A C4A 119.0(18) . . ?
C5A C4A C3A 119.7(19) . . ?
C5A C4A C7A 121.3(19) . . ?
C3A C4A C7A 119.0(19) . . ?
C4A C5A C6A 118.4(19) . . ?
N1A C6A C5A 121.7(19) . . ?
N8A C7A C4A 119(2) . . ?
C7A N8A C9A 120(2) . . ?
C14A C9A N8A 127(2) . . ?
C14A C9A C10A 119(2) . . ?
N8A C9A C10A 114(2) . . ?
C11A C10A C9A 122(2) . . ?
C12A C11A C10A 116(3) . . ?
F12A C12A C11A 118(2) . . ?
F12A C12A C13A 118(2) . . ?
C11A C12A C13A 124(3) . . ?
C12A C13A C14A 117(2) . . ?
C9A C14A C13A 121(2) . . ?
N1B Hg1B Br1B 99.7(4) . . ?
N1B Hg1B Br2B 96.1(4) . . ?
Br1B Hg1B Br2B 164.16(9) . . ?
N1B Hg1B Br1B 93.5(3) . 1_655 ?
Br1B Hg1B Br1B 90.93(7) . 1_655 ?
Br2B Hg1B Br1B 89.65(7) . 1_655 ?
Hg1B Br1B Hg1B 90.93(7) . 1_455 ?
C6B N1B C2B 117.4(17) . . ?
C6B N1B Hg1B 118.6(12) . . ?
C2B N1B Hg1B 123.4(13) . . ?
N1B C2B C3B 123.7(18) . . ?
C2B C3B C4B 118.0(18) . . ?
C5B C4B C3B 119.2(18) . . ?
C5B C4B C7B 117.9(19) . . ?
C3B C4B C7B 122.9(19) . . ?
C4B C5B C6B 119.3(18) . . ?
N1B C6B C5B 122.5(18) . . ?
N8B C7B C4B 119(2) . . ?
C7B N8B C9B 120(2) . . ?
C14B C9B C10B 118(2) . . ?
C14B C9B N8B 124(2) . . ?
C10B C9B N8B 118(2) . . ?
C11B C10B C9B 122(2) . . ?
C10B C11B C12B 118(2) . . ?
F12B C12B C13B 118(2) . . ?
F12B C12B C11B 118(2) . . ?
C13B C12B C11B 124(2) . . ?
C12B C13B C14B 117(2) . . ?
C13B C14B C9B 121(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
C6A N1A C2A C3A 0.0(3) . . . . ?
Hg1A N1A C2A C3A 177.5(9) . . . . ?
N1A C2A C3A C4A 0.0(3) . . . . ?
C2A C3A C4A C5A 0.1(7) . . . . ?
C2A C3A C4A C7A -178.6(15) . . . . ?
C3A C4A C5A C6A -0.1(9) . . . . ?
C7A C4A C5A C6A 178.6(16) . . . . ?
C2A N1A C6A C5A 0.0(7) . . . . ?
Hg1A N1A C6A C5A -177.5(10) . . . . ?
C4A C5A C6A N1A 0.0(9) . . . . ?
C5A C4A C7A N8A 15(2) . . . . ?
C3A C4A C7A N8A -166.8(16) . . . . ?
C4A C7A N8A C9A 175.5(17) . . . . ?
C7A N8A C9A C14A -12(3) . . . . ?
C7A N8A C9A C10A 164.0(16) . . . . ?
C14A C9A C10A C11A 0.0(3) . . . . ?
N8A C9A C10A C11A -176.6(15) . . . . ?
C9A C10A C11A C12A 0.1(3) . . . . ?
C10A C11A C12A F12A -177.3(16) . . . . ?
C10A C11A C12A C13A -0.2(7) . . . . ?
F12A C12A C13A C14A 177.3(16) . . . . ?
C11A C12A C13A C14A 0.2(9) . . . . ?
N8A C9A C14A C13A 176.2(17) . . . . ?
C10A C9A C14A C13A 0.1(7) . . . . ?
C12A C13A C14A C9A -0.2(8) . . . . ?
C6B N1B C2B C3B 0.0(3) . . . . ?
Hg1B N1B C2B C3B -171.0(9) . . . . ?
N1B C2B C3B C4B 0.1(3) . . . . ?
C2B C3B C4B C5B -0.2(7) . . . . ?
C2B C3B C4B C7B 176.8(17) . . . . ?
C3B C4B C5B C6B 0.3(9) . . . . ?
C7B C4B C5B C6B -176.9(16) . . . . ?
C2B N1B C6B C5B 0.1(7) . . . . ?
Hg1B N1B C6B C5B 171.5(10) . . . . ?
C4B C5B C6B N1B -0.2(10) . . . . ?
C5B C4B C7B N8B 164.2(18) . . . . ?
C3B C4B C7B N8B -13(3) . . . . ?
C4B C7B N8B C9B -178.2(17) . . . . ?
C7B N8B C9B C14B 18(3) . . . . ?
C7B N8B C9B C10B -160.5(18) . . . . ?
C14B C9B C10B C11B 0.0(3) . . . . ?
N8B C9B C10B C11B 178.5(15) . . . . ?
C9B C10B C11B C12B 0.0(3) . . . . ?
C10B C11B C12B F12B -179.1(15) . . . . ?
C10B C11B C12B C13B 0.1(7) . . . . ?
F12B C12B C13B C14B 179.0(16) . . . . ?
C11B C12B C13B C14B -0.2(9) . . . . ?
C12B C13B C14B C9B 0.2(9) . . . . ?
C10B C9B C14B C13B -0.1(7) . . . . ?
N8B C9B C14B C13B -178.5(16) . . . . ?


_refine_diff_density_max         6.153
_refine_diff_density_min         -3.734
_refine_diff_density_rms         0.521

_shelxl_version_number           2013-4



####################################################################### 
# 
# 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_2_lt
_database_code_depnum_ccdc_archive 'CCDC 1034447'
_audit_update_record             
;
2015-01-29 deposited with the CCDC.
2015-02-10 downloaded from the CCDC.
;
_audit_creation_method           SHELXL-2013
_chemical_name_systematic        
;
 ?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C12 H9 Br2 Cl Hg N2'
_chemical_formula_sum            'C12 H9 Br2 Cl Hg N2'
_chemical_formula_weight         577.07

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
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'

_space_group_crystal_system      orthorhombic
_space_group_IT_number           19
_space_group_name_H-M_alt        'P 21 21 21'
_space_group_name_Hall           'P 2ac 2ab'

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

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

_cell_length_a                   4.7120(2)
_cell_length_b                   16.4085(7)
_cell_length_c                   17.6773(8)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     1366.75(10)
_cell_formula_units_Z            4
_cell_measurement_temperature    100(1)
_cell_measurement_reflns_used    5149
_cell_measurement_theta_min      3.3780
_cell_measurement_theta_max      28.0570

_exptl_crystal_description       prism
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    2.804
_exptl_crystal_F_000             1048
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.4
_exptl_crystal_size_mid          0.06
_exptl_crystal_size_min          0.06
_exptl_absorpt_coefficient_mu    17.285
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_T_min  0.33478
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.33 (release 27-03-2014 CrysAlis171 .NET)
(compiled Mar 27 2014,17:12:48)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;

_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      100(1)
_diffrn_radiation_wavelength     0.7107
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_source         'Enhance (Mo) X-ray Source'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Xcalibur, Eos'
_diffrn_detector_area_resol_mean 16.1544
_diffrn_measurement_method       ω-scan
_diffrn_reflns_number            12993
_diffrn_reflns_av_unetI/netI     0.0365
_diffrn_reflns_av_R_equivalents  0.0475
_diffrn_reflns_limit_h_min       -5
_diffrn_reflns_limit_h_max       5
_diffrn_reflns_limit_k_min       -19
_diffrn_reflns_limit_k_max       20
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_theta_min         3.388
_diffrn_reflns_theta_max         25.993
_diffrn_reflns_theta_full        25.000
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measured_fraction_theta_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.996
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_point_group_measured_fraction_full 0.998
_reflns_number_total             2680
_reflns_number_gt                2595
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.681
_reflns_Friedel_fraction_max     0.997
_reflns_Friedel_fraction_full    1.000

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

_computing_data_collection       'CrysAlis Pro (Agilent Technologies (2011))'
_computing_cell_refinement       'CrysAlis Pro (Agilent Technologies (2011))'
_computing_data_reduction        'CrysAlis Pro (Agilent Technologies (2011))'
_computing_structure_solution    'SIR92 (Altomare et al., 1993)'
_computing_structure_refinement  'SHELXL-2013 (Sheldrick, 2013)'
_computing_molecular_graphics    'Mercury (MacRae et al., 2009)'
_computing_publication_material  'SHELXL-2013 (Sheldrick, 2013)'

_refine_special_details          
;
 ISOR restraints were aplied for one C atom, in order to avoid wxcentric 
shapes of the ellipsoid

;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0221P)²] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_abs_structure_details 
;
 Flack x determined using 1023 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons and Flack (2004), Acta Cryst. A60, s61).
;
_refine_ls_abs_structure_Flack   -0.018(6)
_chemical_absolute_configuration ?
_refine_ls_number_reflns         2680
_refine_ls_number_parameters     163
_refine_ls_number_restraints     6
_refine_ls_R_factor_all          0.0238
_refine_ls_R_factor_gt           0.0221
_refine_ls_wR_factor_ref         0.0484
_refine_ls_wR_factor_gt          0.0473
_refine_ls_goodness_of_fit_ref   1.034
_refine_ls_restrained_S_all      1.033
_refine_ls_shift/su_max          0.002
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
N1 N 0.2992(12) 1.0563(4) 0.5390(3) 0.0096(14) Uani 1 1 d . . . . .
Hg1 Hg -0.03078(6) 1.14516(2) 0.47693(2) 0.01184(9) Uani 1 1 d . . . . .
Br1 Br -0.11434(18) 1.07251(5) 0.35727(4) 0.0173(2) Uani 1 1 d . . . . .
Br2 Br -0.13409(17) 1.23181(5) 0.58949(4) 0.01394(19) Uani 1 1 d . . . . .
C2 C 0.4294(15) 0.9987(4) 0.4987(4) 0.0110(17) Uani 1 1 d . . . . .
H2 H 0.3826 0.9928 0.4467 0.013 Uiso 1 1 calc R U . . .
C3 C 0.6305(15) 0.9469(5) 0.5299(5) 0.0143(17) Uani 1 1 d . . . . .
H3 H 0.7221 0.9074 0.4991 0.017 Uiso 1 1 calc R U . . .
C4 C 0.6983(15) 0.9530(5) 0.6067(4) 0.0087(16) Uani 1 1 d . U . . .
C5 C 0.5585(17) 1.0121(5) 0.6473(4) 0.0136(17) Uani 1 1 d . . . . .
H5 H 0.5977 1.0181 0.6997 0.016 Uiso 1 1 calc R U . . .
C6 C 0.3622(16) 1.0629(5) 0.6134(4) 0.0130(17) Uani 1 1 d . . . . .
H6 H 0.2697 1.1033 0.6430 0.016 Uiso 1 1 calc R U . . .
C7 C 0.9125(17) 0.8994(5) 0.6406(4) 0.0138(17) Uani 1 1 d . . . . .
H7 H 0.9510 0.9029 0.6932 0.017 Uiso 1 1 calc R U . . .
N8 N 1.0473(13) 0.8484(4) 0.6000(3) 0.0109(13) Uani 1 1 d . . . . .
C9 C 1.2510(16) 0.7952(5) 0.6308(5) 0.0128(18) Uani 1 1 d . . . . .
C10 C 1.3476(16) 0.7944(5) 0.7062(4) 0.0111(17) Uani 1 1 d . . . . .
H10 H 1.2716 0.8320 0.7417 0.013 Uiso 1 1 calc R U . . .
C11 C 1.5524(17) 0.7392(5) 0.7289(4) 0.0126(17) Uani 1 1 d . . . . .
H11 H 1.6183 0.7394 0.7797 0.015 Uiso 1 1 calc R U . . .
C12 C 1.6613(16) 0.6835(5) 0.6777(4) 0.0103(17) Uani 1 1 d . . . . .
Cl12 Cl 1.9145(4) 0.61241(12) 0.70499(11) 0.0152(4) Uani 1 1 d . . . . .
C13 C 1.5730(16) 0.6840(5) 0.6028(4) 0.0132(17) Uani 1 1 d . . . . .
H13 H 1.6504 0.6464 0.5675 0.016 Uiso 1 1 calc R U . . .
C14 C 1.3709(16) 0.7399(5) 0.5805(4) 0.0108(16) Uani 1 1 d . . . . .
H14 H 1.3118 0.7407 0.5291 0.013 Uiso 1 1 calc R U . . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
N1 C2 1.333(9) . ?
N1 C6 1.353(9) . ?
N1 Hg1 2.398(6) . ?
Hg1 Br1 2.4598(8) . ?
Hg1 Br2 2.4935(8) . ?
Hg1 Br2 2.9914(8) 3_576 ?
Br2 Hg1 2.9914(8) 3_476 ?
C2 C3 1.387(10) . ?
C3 C4 1.398(10) . ?
C4 C5 1.374(11) . ?
C4 C7 1.467(11) . ?
C5 C6 1.382(10) . ?
C7 N8 1.273(10) . ?
N8 C9 1.406(10) . ?
C9 C14 1.391(11) . ?
C9 C10 1.409(10) . ?
C10 C11 1.383(10) . ?
C11 C12 1.385(10) . ?
C12 C13 1.387(10) . ?
C12 Cl12 1.737(8) . ?
C13 C14 1.380(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 N1 C6 118.4(7) . . ?
C2 N1 Hg1 119.1(5) . . ?
C6 N1 Hg1 122.6(5) . . ?
N1 Hg1 Br1 101.68(15) . . ?
N1 Hg1 Br2 96.22(14) . . ?
Br1 Hg1 Br2 158.64(3) . . ?
N1 Hg1 Br2 100.66(14) . 3_576 ?
Br1 Hg1 Br2 95.14(3) . 3_576 ?
Br2 Hg1 Br2 92.89(2) . 3_576 ?
Hg1 Br2 Hg1 101.16(3) . 3_476 ?
N1 C2 C3 122.5(7) . . ?
C2 C3 C4 119.8(7) . . ?
C5 C4 C3 116.6(7) . . ?
C5 C4 C7 122.6(7) . . ?
C3 C4 C7 120.7(7) . . ?
C4 C5 C6 121.3(7) . . ?
N1 C6 C5 121.3(7) . . ?
N8 C7 C4 120.5(7) . . ?
C7 N8 C9 122.1(7) . . ?
C14 C9 N8 115.8(7) . . ?
C14 C9 C10 117.8(7) . . ?
N8 C9 C10 126.4(7) . . ?
C11 C10 C9 120.5(7) . . ?
C10 C11 C12 120.0(7) . . ?
C11 C12 C13 120.6(7) . . ?
C11 C12 Cl12 121.0(6) . . ?
C13 C12 Cl12 118.4(6) . . ?
C14 C13 C12 118.9(7) . . ?
C13 C14 C9 122.1(7) . . ?

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
C6 N1 C2 C3 -1.5(11) . . . . ?
Hg1 N1 C2 C3 177.6(5) . . . . ?
N1 C2 C3 C4 1.5(12) . . . . ?
C2 C3 C4 C5 -0.5(11) . . . . ?
C2 C3 C4 C7 -179.4(7) . . . . ?
C3 C4 C5 C6 -0.3(11) . . . . ?
C7 C4 C5 C6 178.5(7) . . . . ?
C2 N1 C6 C5 0.6(11) . . . . ?
Hg1 N1 C6 C5 -178.4(6) . . . . ?
C4 C5 C6 N1 0.3(12) . . . . ?
C5 C4 C7 N8 -176.4(7) . . . . ?
C3 C4 C7 N8 2.4(11) . . . . ?
C4 C7 N8 C9 -179.0(7) . . . . ?
C7 N8 C9 C14 176.9(7) . . . . ?
C7 N8 C9 C10 -4.8(12) . . . . ?
C14 C9 C10 C11 -0.9(11) . . . . ?
N8 C9 C10 C11 -179.2(7) . . . . ?
C9 C10 C11 C12 -0.9(12) . . . . ?
C10 C11 C12 C13 1.9(12) . . . . ?
C10 C11 C12 Cl12 -179.0(6) . . . . ?
C11 C12 C13 C14 -1.2(12) . . . . ?
Cl12 C12 C13 C14 179.7(6) . . . . ?
C12 C13 C14 C9 -0.6(12) . . . . ?
N8 C9 C14 C13 -179.8(7) . . . . ?
C10 C9 C14 C13 1.6(11) . . . . ?

_refine_diff_density_max         2.165
_refine_diff_density_min         -1.046
_refine_diff_density_rms         0.158

_shelxl_version_number           2013-4



####################################################################### 
# 
# 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 1034448'
_audit_update_record             
;
2015-01-29 deposited with the CCDC.
2015-02-10 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2013
_chemical_name_systematic        
;
 ?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C24 H18 Br4 Hg N4'
_chemical_formula_sum            'C24 H18 Br4 Hg N4'
_chemical_formula_weight         882.65

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
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'

_space_group_crystal_system      orthorhombic
_space_group_IT_number           43
_space_group_name_H-M_alt        'F d d 2'
_space_group_name_Hall           'F 2 -2d'

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

loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, z'
'-x+1/4, y+1/4, z+1/4'
'x+1/4, -y+1/4, z+1/4'
'x, y+1/2, z+1/2'
'-x, -y+1/2, z+1/2'
'-x+1/4, y+3/4, z+3/4'
'x+1/4, -y+3/4, z+3/4'
'x+1/2, y, z+1/2'
'-x+1/2, -y, z+1/2'
'-x+3/4, y+1/4, z+3/4'
'x+3/4, -y+1/4, z+3/4'
'x+1/2, y+1/2, z'
'-x+1/2, -y+1/2, z'
'-x+3/4, y+3/4, z+1/4'
'x+3/4, -y+3/4, z+1/4'

_cell_length_a                   26.9001(7)
_cell_length_b                   37.9178(9)
_cell_length_c                   4.8030(2)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     4899.0(3)
_cell_formula_units_Z            8
_cell_measurement_temperature    100(1)
_cell_measurement_reflns_used    4543
_cell_measurement_theta_min      3.1920
_cell_measurement_theta_max      27.9250

_exptl_crystal_description       needle
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    2.393
_exptl_crystal_F_000             3280
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.3
_exptl_crystal_size_mid          0.05
_exptl_crystal_size_min          0.05
_exptl_absorpt_coefficient_mu    12.830
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_T_min  0.29231
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.31 (release 14-01-2014 CrysAlis171 .NET)
(compiled Jan 14 2014,18:38:05)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;

_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      100(1)
_diffrn_radiation_wavelength     0.7107
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_source         'Enhance (Mo) X-ray Source'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Xcalibur, Eos'
_diffrn_detector_area_resol_mean 16.1544
_diffrn_measurement_method       ω-scan
_diffrn_reflns_number            8916
_diffrn_reflns_av_unetI/netI     0.0477
_diffrn_reflns_av_R_equivalents  0.0611
_diffrn_reflns_limit_h_min       -34
_diffrn_reflns_limit_h_max       35
_diffrn_reflns_limit_k_min       -49
_diffrn_reflns_limit_k_max       49
_diffrn_reflns_limit_l_min       -6
_diffrn_reflns_limit_l_max       6
_diffrn_reflns_theta_min         3.029
_diffrn_reflns_theta_max         28.152
_diffrn_reflns_theta_full        25.000
_diffrn_measured_fraction_theta_max 0.937
_diffrn_measured_fraction_theta_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.937
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.827
_diffrn_reflns_point_group_measured_fraction_full 0.943
_reflns_number_total             2491
_reflns_number_gt                2349
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.582
_reflns_Friedel_fraction_max     0.689
_reflns_Friedel_fraction_full    0.872

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

_computing_data_collection       'CrysAlis Pro (Agilent Technologies (2011))'
_computing_cell_refinement       'CrysAlis Pro (Agilent Technologies (2011))'
_computing_data_reduction        'CrysAlis Pro (Agilent Technologies (2011))'
_computing_structure_solution    'SIR92 (Altomare et al., 1993)'
_computing_structure_refinement  'SHELXL-2013 (Sheldrick, 2013)'
_computing_molecular_graphics    'Mercury (MacRae et al., 2009)'
_computing_publication_material  'SHELXL-2013 (Sheldrick, 2013)'

_refine_special_details          
;
High residual density peaks are observed close to Hg atom (around 0.9A)
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0520P)²+2.3329P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_abs_structure_details 
;
 Flack x determined using 826 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons and Flack (2004), Acta Cryst. A60, s61).
;
_refine_ls_abs_structure_Flack   -0.009(12)
_chemical_absolute_configuration ?
_refine_ls_number_reflns         2491
_refine_ls_number_parameters     150
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0402
_refine_ls_R_factor_gt           0.0369
_refine_ls_wR_factor_ref         0.0911
_refine_ls_wR_factor_gt          0.0891
_refine_ls_goodness_of_fit_ref   1.125
_refine_ls_restrained_S_all      1.125
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Hg1 Hg 0.0000 1.0000 -0.81472(10) 0.01452(16) Uani 1 2 d S T P . .
Br1 Br -0.04437(4) 0.94422(3) -0.9359(3) 0.0202(3) Uani 1 1 d . . . . .
N1 N 0.0607(3) 0.9743(2) -0.5067(19) 0.0136(19) Uani 1 1 d . . . . .
C2 C 0.0607(4) 0.9399(3) -0.435(3) 0.017(2) Uani 1 1 d . . . . .
H2 H 0.0368 0.9248 -0.5180 0.020 Uiso 1 1 calc R U . . .
C3 C 0.0935(4) 0.9259(3) -0.246(2) 0.016(2) Uani 1 1 d . . . . .
H3 H 0.0921 0.9016 -0.2019 0.019 Uiso 1 1 calc R U . . .
C4 C 0.1290(4) 0.9476(3) -0.120(2) 0.012(2) Uani 1 1 d . . . . .
C5 C 0.1293(4) 0.9831(3) -0.195(2) 0.014(2) Uani 1 1 d . . . . .
H5 H 0.1524 0.9989 -0.1125 0.016 Uiso 1 1 calc R U . . .
C6 C 0.0960(4) 0.9949(3) -0.391(3) 0.015(2) Uani 1 1 d . . . . .
H6 H 0.0979 1.0189 -0.4485 0.018 Uiso 1 1 calc R U . . .
C7 C 0.1633(4) 0.9331(2) 0.088(2) 0.013(2) Uani 1 1 d . . . . .
H7 H 0.1641 0.9084 0.1200 0.015 Uiso 1 1 calc R U . . .
N8 N 0.1920(3) 0.9532(2) 0.224(2) 0.014(2) Uani 1 1 d . . . . .
C9 C 0.2253(4) 0.9393(2) 0.427(2) 0.0108(19) Uani 1 1 d . . . . .
C10 C 0.2265(4) 0.9048(3) 0.523(2) 0.014(2) Uani 1 1 d . . . . .
H10 H 0.2034 0.8881 0.4524 0.017 Uiso 1 1 calc R U . . .
C11 C 0.2616(4) 0.8946(3) 0.724(2) 0.015(2) Uani 1 1 d . . . . .
H11 H 0.2623 0.8710 0.7921 0.018 Uiso 1 1 calc R U . . .
C12 C 0.2950(4) 0.9193(3) 0.821(3) 0.013(2) Uani 1 1 d . . . . .
Br12 Br 0.34417(4) 0.90572(3) 1.0857(2) 0.0166(2) Uani 1 1 d . . . . .
C13 C 0.2941(4) 0.9537(3) 0.733(2) 0.013(2) Uani 1 1 d . . . . .
H13 H 0.3172 0.9704 0.8035 0.015 Uiso 1 1 calc R U . . .
C14 C 0.2589(4) 0.9635(3) 0.538(2) 0.013(2) Uani 1 1 d . . . . .
H14 H 0.2574 0.9874 0.4792 0.016 Uiso 1 1 calc R U . . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Hg1 N1 2.409(9) 2_575 ?
Hg1 N1 2.410(9) . ?
Hg1 Br1 2.4975(11) . ?
Hg1 Br1 2.4975(11) 2_575 ?
N1 C2 1.347(13) . ?
N1 C6 1.350(13) . ?
C2 C3 1.371(16) . ?
C2 H2 0.9500 . ?
C3 C4 1.399(14) . ?
C3 H3 0.9500 . ?
C4 C5 1.393(14) . ?
C4 C7 1.466(14) . ?
C5 C6 1.376(16) . ?
C5 H5 0.9500 . ?
C6 H6 0.9500 . ?
C7 N8 1.267(13) . ?
C7 H7 0.9500 . ?
N8 C9 1.424(13) . ?
C9 C10 1.386(14) . ?
C9 C14 1.395(14) . ?
C10 C11 1.407(16) . ?
C10 H10 0.9500 . ?
C11 C12 1.379(15) . ?
C11 H11 0.9500 . ?
C12 C13 1.374(14) . ?
C12 Br12 1.903(11) . ?
C13 C14 1.381(15) . ?
C13 H13 0.9500 . ?
C14 H14 0.9500 . ?

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 Hg1 N1 104.2(4) 2_575 . ?
N1 Hg1 Br1 99.3(2) 2_575 . ?
N1 Hg1 Br1 97.1(2) . . ?
N1 Hg1 Br1 97.1(2) 2_575 2_575 ?
N1 Hg1 Br1 99.3(2) . 2_575 ?
Br1 Hg1 Br1 153.05(6) . 2_575 ?
C2 N1 C6 117.1(9) . . ?
C2 N1 Hg1 123.3(7) . . ?
C6 N1 Hg1 119.6(7) . . ?
N1 C2 C3 122.9(10) . . ?
N1 C2 H2 118.5 . . ?
C3 C2 H2 118.5 . . ?
C2 C3 C4 120.0(9) . . ?
C2 C3 H3 120.0 . . ?
C4 C3 H3 120.0 . . ?
C5 C4 C3 117.2(9) . . ?
C5 C4 C7 122.4(9) . . ?
C3 C4 C7 120.3(9) . . ?
C6 C5 C4 119.3(9) . . ?
C6 C5 H5 120.3 . . ?
C4 C5 H5 120.3 . . ?
N1 C6 C5 123.3(10) . . ?
N1 C6 H6 118.3 . . ?
C5 C6 H6 118.3 . . ?
N8 C7 C4 120.6(9) . . ?
N8 C7 H7 119.7 . . ?
C4 C7 H7 119.7 . . ?
C7 N8 C9 120.9(9) . . ?
C10 C9 C14 118.6(10) . . ?
C10 C9 N8 126.2(9) . . ?
C14 C9 N8 115.2(9) . . ?
C9 C10 C11 120.3(10) . . ?
C9 C10 H10 119.9 . . ?
C11 C10 H10 119.9 . . ?
C12 C11 C10 118.9(10) . . ?
C12 C11 H11 120.6 . . ?
C10 C11 H11 120.6 . . ?
C13 C12 C11 121.9(10) . . ?
C13 C12 Br12 118.4(8) . . ?
C11 C12 Br12 119.7(8) . . ?
C12 C13 C14 118.6(10) . . ?
C12 C13 H13 120.7 . . ?
C14 C13 H13 120.7 . . ?
C13 C14 C9 121.7(10) . . ?
C13 C14 H14 119.2 . . ?
C9 C14 H14 119.2 . . ?

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
C6 N1 C2 C3 2.1(17) . . . . ?
Hg1 N1 C2 C3 -176.0(9) . . . . ?
N1 C2 C3 C4 0.0(18) . . . . ?
C2 C3 C4 C5 -0.4(16) . . . . ?
C2 C3 C4 C7 178.2(10) . . . . ?
C3 C4 C5 C6 -1.2(15) . . . . ?
C7 C4 C5 C6 -179.9(10) . . . . ?
C2 N1 C6 C5 -3.9(16) . . . . ?
Hg1 N1 C6 C5 174.3(8) . . . . ?
C4 C5 C6 N1 3.5(16) . . . . ?
C5 C4 C7 N8 6.1(16) . . . . ?
C3 C4 C7 N8 -172.5(10) . . . . ?
C4 C7 N8 C9 179.7(9) . . . . ?
C7 N8 C9 C10 -8.4(16) . . . . ?
C7 N8 C9 C14 172.7(10) . . . . ?
C14 C9 C10 C11 -1.3(16) . . . . ?
N8 C9 C10 C11 179.8(9) . . . . ?
C9 C10 C11 C12 -0.7(16) . . . . ?
C10 C11 C12 C13 1.7(17) . . . . ?
C10 C11 C12 Br12 -178.2(8) . . . . ?
C11 C12 C13 C14 -0.7(17) . . . . ?
Br12 C12 C13 C14 179.2(8) . . . . ?
C12 C13 C14 C9 -1.5(17) . . . . ?
C10 C9 C14 C13 2.5(16) . . . . ?
N8 C9 C14 C13 -178.6(9) . . . . ?

_refine_diff_density_max         4.192
_refine_diff_density_min         -2.168
_refine_diff_density_rms         0.251

_shelxl_version_number           2013-4



####################################################################### 
# 
# 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_4
_database_code_depnum_ccdc_archive 'CCDC 1034449'
_audit_update_record             
;
2015-01-29 deposited with the CCDC.
2015-02-10 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2013
_chemical_name_systematic        
;
 ?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C12 H9 Br2 Hg I N2'
_chemical_formula_sum            'C12 H9 Br2 Hg I N2'
_chemical_formula_weight         668.52


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'
I I -0.4742 1.8119 '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'

_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 21/c'
_space_group_name_Hall           '-P 2ybc'

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

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

_cell_length_a                   4.0584(2)
_cell_length_b                   23.4890(6)
_cell_length_c                   15.5548(5)
_cell_angle_alpha                90
_cell_angle_beta                 94.887(3)
_cell_angle_gamma                90
_cell_volume                     1477.41(9)
_cell_formula_units_Z            4
_cell_measurement_temperature    100(1)
_cell_measurement_reflns_used    22378
_cell_measurement_theta_min      3.4520
_cell_measurement_theta_max      28.3170

_exptl_crystal_description       plate
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    3.006
_exptl_crystal_F_000             1192
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.3
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.05
_exptl_absorpt_coefficient_mu    17.900
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_T_min  0.10084
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;

_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      100(1)
_diffrn_radiation_wavelength     0.7107
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_source         'Enhance (Mo) X-ray Source'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Xcalibur, Eos'
_diffrn_detector_area_resol_mean 16.1544
_diffrn_measurement_method       ω-scan
_diffrn_reflns_number            2600
_diffrn_reflns_av_unetI/netI     0.0280
_diffrn_reflns_av_R_equivalents  ?
_diffrn_reflns_limit_h_min       -4
_diffrn_reflns_limit_h_max       4
_diffrn_reflns_limit_k_min       -27
_diffrn_reflns_limit_k_max       27
_diffrn_reflns_limit_l_min       -2
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_theta_min         2.768
_diffrn_reflns_theta_max         24.998
_diffrn_reflns_theta_full        25.000
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measured_fraction_theta_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_point_group_measured_fraction_full 0.998
_reflns_number_total             2600
_reflns_number_gt                2526
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_reflns_special_details          
;
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;

_computing_data_collection       'CrysAlis Pro (Agilent Technologies (2011))'
_computing_cell_refinement       'CrysAlis Pro (Agilent Technologies (2011))'
_computing_data_reduction        'CrysAlis Pro (Agilent Technologies (2011))'
_computing_structure_solution    'SIR92 (Altomare et al., 1993)'
_computing_structure_refinement  'SHELXL-2013 (Sheldrick, 2013)'
_computing_molecular_graphics    'Mercury (MacRae et al., 2009)'
_computing_publication_material  'SHELXL-2013 (Sheldrick, 2013)'

_refine_special_details          
;
Refined as a 2-component twin.
High residual density peaks are observed close to Hg atom (around 1A).
Restraints to avoid excentric shapes of ellipsoids (ISOR) for C atoms have 
been used.
;

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0500P)²+255.7889P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         2600
_refine_ls_number_parameters     164
_refine_ls_number_restraints     72
_refine_ls_R_factor_all          0.0797
_refine_ls_R_factor_gt           0.0783
_refine_ls_wR_factor_ref         0.2151
_refine_ls_wR_factor_gt          0.2144
_refine_ls_goodness_of_fit_ref   1.204
_refine_ls_restrained_S_all      1.188
_refine_ls_shift/su_max          0.009
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
N1 N 0.739(6) 0.3039(9) 0.9255(14) 0.020(5) Uani 1 1 d . . . . .
Hg1 Hg 0.7604(2) 0.24295(4) 0.80357(6) 0.0174(3) Uani 1 1 d . . . . .
Br1 Br 1.1608(7) 0.16912(11) 0.85641(17) 0.0222(6) Uani 1 1 d . . . . .
Br2 Br 0.3738(6) 0.29234(11) 0.69786(16) 0.0185(6) Uani 1 1 d . . . . .
C2 C 0.880(7) 0.2891(12) 1.0038(18) 0.025(6) Uani 1 1 d . U . . .
H2 H 0.9964 0.2541 1.0102 0.030 Uiso 1 1 calc R U . . .
C3 C 0.859(7) 0.3235(11) 1.0748(17) 0.019(5) Uani 1 1 d . U . . .
H3 H 0.9644 0.3125 1.1291 0.023 Uiso 1 1 calc R U . . .
C4 C 0.683(7) 0.3746(12) 1.0673(17) 0.022(6) Uani 1 1 d . U . . .
C5 C 0.539(6) 0.3890(11) 0.9855(16) 0.018(5) Uani 1 1 d . U . . .
H5 H 0.4161 0.4233 0.9771 0.021 Uiso 1 1 calc R U . . .
C6 C 0.576(7) 0.3535(11) 0.9176(16) 0.019(5) Uani 1 1 d . U . . .
H6 H 0.4817 0.3644 0.8621 0.023 Uiso 1 1 calc R U . . .
C7 C 0.643(7) 0.4088(11) 1.1437(17) 0.021(6) Uani 1 1 d . U . . .
H7 H 0.7779 0.4019 1.1956 0.025 Uiso 1 1 calc R U . . .
N8 N 0.422(6) 0.4488(10) 1.1401(13) 0.026(5) Uani 1 1 d . . . . .
C9 C 0.376(7) 0.4812(11) 1.2156(16) 0.018(5) Uani 1 1 d . U . . .
C10 C 0.190(7) 0.5299(12) 1.1998(17) 0.023(6) Uani 1 1 d . U . . .
H10 H 0.1144 0.5399 1.1423 0.028 Uiso 1 1 calc R U . . .
C11 C 0.113(7) 0.5650(11) 1.2693(16) 0.019(5) Uani 1 1 d . U . . .
H11 H -0.0173 0.5983 1.2590 0.023 Uiso 1 1 calc R U . . .
C12 C 0.230(7) 0.5501(11) 1.3524(16) 0.019(5) Uani 1 1 d . U . . .
I12 I 0.1050(5) 0.59951(7) 1.45673(10) 0.0209(4) Uani 1 1 d . . . . .
C13 C 0.419(7) 0.5018(11) 1.3659(17) 0.019(5) Uani 1 1 d . U . . .
H13 H 0.5024 0.4921 1.4229 0.023 Uiso 1 1 calc R U . . .
C14 C 0.490(7) 0.4672(12) 1.2981(17) 0.021(6) Uani 1 1 d . U . . .
H14 H 0.6175 0.4336 1.3088 0.026 Uiso 1 1 calc R U . . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
N1 C6 1.34(3) . ?
N1 C2 1.35(4) . ?
N1 Hg1 2.38(2) . ?
Hg1 Br2 2.464(3) . ?
Hg1 Br1 2.469(3) . ?
C2 C3 1.38(4) . ?
C3 C4 1.40(4) . ?
C4 C5 1.40(4) . ?
C4 C7 1.45(4) . ?
C5 C6 1.36(4) . ?
C7 N8 1.30(4) . ?
N8 C9 1.42(3) . ?
C9 C14 1.37(4) . ?
C9 C10 1.38(4) . ?
C10 C11 1.41(4) . ?
C11 C12 1.39(4) . ?
C12 C13 1.37(4) . ?
C12 I12 2.09(3) . ?
C13 C14 1.38(4) . ?

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
C6 N1 C2 118(2) . . ?
C6 N1 Hg1 120.0(17) . . ?
C2 N1 Hg1 121.5(18) . . ?
N1 Hg1 Br2 100.6(5) . . ?
N1 Hg1 Br1 103.0(6) . . ?
Br2 Hg1 Br1 156.41(10) . . ?
N1 C2 C3 122(3) . . ?
C2 C3 C4 120(3) . . ?
C3 C4 C5 117(2) . . ?
C3 C4 C7 120(2) . . ?
C5 C4 C7 123(2) . . ?
C6 C5 C4 119(2) . . ?
N1 C6 C5 123(3) . . ?
N8 C7 C4 119(2) . . ?
C7 N8 C9 119(2) . . ?
C14 C9 C10 120(2) . . ?
C14 C9 N8 126(2) . . ?
C10 C9 N8 114(2) . . ?
C9 C10 C11 120(2) . . ?
C12 C11 C10 119(2) . . ?
C13 C12 C11 120(2) . . ?
C13 C12 I12 120.6(19) . . ?
C11 C12 I12 120(2) . . ?
C12 C13 C14 121(2) . . ?
C9 C14 C13 120(3) . . ?

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
C6 N1 C2 C3 0(4) . . . . ?
Hg1 N1 C2 C3 -178(2) . . . . ?
N1 C2 C3 C4 1(4) . . . . ?
C2 C3 C4 C5 -1(4) . . . . ?
C2 C3 C4 C7 176(3) . . . . ?
C3 C4 C5 C6 0(4) . . . . ?
C7 C4 C5 C6 -177(3) . . . . ?
C2 N1 C6 C5 -2(4) . . . . ?
Hg1 N1 C6 C5 176(2) . . . . ?
C4 C5 C6 N1 2(4) . . . . ?
C3 C4 C7 N8 -165(3) . . . . ?
C5 C4 C7 N8 12(4) . . . . ?
C4 C7 N8 C9 178(2) . . . . ?
C7 N8 C9 C14 -15(4) . . . . ?
C7 N8 C9 C10 166(3) . . . . ?
C14 C9 C10 C11 -1(4) . . . . ?
N8 C9 C10 C11 177(2) . . . . ?
C9 C10 C11 C12 1(4) . . . . ?
C10 C11 C12 C13 0(4) . . . . ?
C10 C11 C12 I12 -178(2) . . . . ?
C11 C12 C13 C14 -1(4) . . . . ?
I12 C12 C13 C14 177(2) . . . . ?
C10 C9 C14 C13 0(4) . . . . ?
N8 C9 C14 C13 -178(3) . . . . ?
C12 C13 C14 C9 1(4) . . . . ?

_refine_diff_density_max         9.656
_refine_diff_density_min         -3.936
_refine_diff_density_rms         0.580

_shelxl_version_number           2013-4



####################################################################### 
# 
# 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_5
_database_code_depnum_ccdc_archive 'CCDC 1034450'
_audit_update_record             
;
2015-01-29 deposited with the CCDC.
2015-02-10 downloaded from the CCDC.
;


_audit_creation_method           SHELXL-2013
_chemical_name_systematic        
;
 ?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C12 H9 F Hg I2 N2'
_chemical_formula_sum            'C12 H9 F Hg I2 N2'
_chemical_formula_weight         654.60

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'
I I -0.4742 1.8119 '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'

_space_group_crystal_system      orthorhombic
_space_group_IT_number           43
_space_group_name_H-M_alt        'F d d 2'
_space_group_name_Hall           'F 2 -2d'

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

loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, z'
'-x+1/4, y+1/4, z+1/4'
'x+1/4, -y+1/4, z+1/4'
'x, y+1/2, z+1/2'
'-x, -y+1/2, z+1/2'
'-x+1/4, y+3/4, z+3/4'
'x+1/4, -y+3/4, z+3/4'
'x+1/2, y, z+1/2'
'-x+1/2, -y, z+1/2'
'-x+3/4, y+1/4, z+3/4'
'x+3/4, -y+1/4, z+3/4'
'x+1/2, y+1/2, z'
'-x+1/2, -y+1/2, z'
'-x+3/4, y+3/4, z+1/4'
'x+3/4, -y+3/4, z+1/4'

_cell_length_a                   37.6061(3)
_cell_length_b                   38.3258(8)
_cell_length_c                   4.2956(2)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     6191.2(3)
_cell_formula_units_Z            16
_cell_measurement_temperature    100(1)
_cell_measurement_reflns_used    13207
_cell_measurement_theta_min      3.0150
_cell_measurement_theta_max      26.2010

_exptl_crystal_description       prism
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    2.809
_exptl_crystal_F_000             4640
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.25
_exptl_crystal_size_mid          0.08
_exptl_crystal_size_min          0.08
_exptl_absorpt_coefficient_mu    13.928
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_T_min  0.15643
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.32 (release 02-08-2013 CrysAlis171 .NET)
(compiled Aug  2 2013,16:46:58)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;

_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      100(1)
_diffrn_radiation_wavelength     0.7107
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_source         'Enhance (Mo) X-ray Source'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Xcalibur, Eos'
_diffrn_detector_area_resol_mean 16.1544
_diffrn_measurement_method       ω-scan
_diffrn_reflns_number            59704
_diffrn_reflns_av_unetI/netI     0.0227
_diffrn_reflns_av_R_equivalents  0.0677
_diffrn_reflns_limit_h_min       -46
_diffrn_reflns_limit_h_max       46
_diffrn_reflns_limit_k_min       0
_diffrn_reflns_limit_k_max       46
_diffrn_reflns_limit_l_min       -5
_diffrn_reflns_limit_l_max       5
_diffrn_reflns_theta_min         3.036
_diffrn_reflns_theta_max         25.991
_diffrn_reflns_theta_full        25.000
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measured_fraction_theta_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_point_group_measured_fraction_full 0.998
_reflns_number_total             3050
_reflns_number_gt                2869
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.755
_reflns_Friedel_fraction_max     1.000
_reflns_Friedel_fraction_full    1.000

_reflns_special_details          
;
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;

_computing_data_collection       'CrysAlis Pro (Agilent Technologies (2011))'
_computing_cell_refinement       'CrysAlis Pro (Agilent Technologies (2011))'
_computing_data_reduction        'CrysAlis Pro (Agilent Technologies (2011))'
_computing_structure_solution    'SIR92 (Altomare et al., 1993)'
_computing_structure_refinement  'SHELXL-2013 (Sheldrick, 2013)'
_computing_molecular_graphics    'Mercury (MacRae et al., 2009)'
_computing_publication_material  'SHELXL-2013 (Sheldrick, 2013)'

_refine_special_details          
;
Refined as a 2-component twin.
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0350P)²+2.5020P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_abs_structure_details 
;
 Flack x determined using 1170 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons and Flack (2004), Acta Cryst. A60, s61).
;
_refine_ls_abs_structure_Flack   -0.007(3)
_chemical_absolute_configuration ?
_refine_ls_number_reflns         3050
_refine_ls_number_parameters     164
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0283
_refine_ls_R_factor_gt           0.0251
_refine_ls_wR_factor_ref         0.0598
_refine_ls_wR_factor_gt          0.0584
_refine_ls_goodness_of_fit_ref   1.024
_refine_ls_restrained_S_all      1.024
_refine_ls_shift/su_max          0.002
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
N1 N -0.0152(2) 0.87896(19) 0.832(2) 0.054(2) Uani 1 1 d . . . . .
Hg1 Hg -0.05658(2) 0.83078(2) 0.88121(10) 0.05513(14) Uani 1 1 d . . . . .
I1 I -0.11126(2) 0.85507(2) 0.56917(15) 0.05643(19) Uani 1 1 d . . . . .
I2 I -0.02392(2) 0.78871(2) 1.27210(14) 0.05641(19) Uani 1 1 d . . . . .
C2 C -0.0226(3) 0.9090(3) 0.686(3) 0.061(3) Uani 1 1 d . . . . .
H2 H -0.0461 0.9126 0.6117 0.073 Uiso 1 1 calc R U . . .
C3 C 0.0019(3) 0.9350(3) 0.638(3) 0.063(3) Uani 1 1 d . . . . .
H3 H -0.0046 0.9561 0.5378 0.076 Uiso 1 1 calc R U . . .
C4 C 0.0362(3) 0.9294(2) 0.739(3) 0.051(2) Uani 1 1 d . . . . .
C5 C 0.0442(3) 0.8995(3) 0.890(3) 0.072(4) Uani 1 1 d . . . . .
H5 H 0.0677 0.8955 0.9645 0.086 Uiso 1 1 calc R U . . .
C6 C 0.0179(3) 0.8746(3) 0.933(3) 0.070(3) Uani 1 1 d . . . . .
H6 H 0.0237 0.8537 1.0394 0.084 Uiso 1 1 calc R U . . .
C7 C 0.0647(3) 0.9554(3) 0.684(3) 0.056(3) Uani 1 1 d . . . . .
H7 H 0.0864 0.9533 0.7952 0.067 Uiso 1 1 calc R U . . .
N8 N 0.0609(2) 0.9802(2) 0.497(3) 0.059(2) Uani 1 1 d . . . . .
C9 C 0.0894(3) 1.0031(2) 0.435(3) 0.053(3) Uani 1 1 d . . . . .
C10 C 0.1241(3) 0.9991(3) 0.542(3) 0.069(3) Uani 1 1 d . . . . .
H10 H 0.1300 0.9795 0.6672 0.083 Uiso 1 1 calc R U . . .
C11 C 0.1503(3) 1.0233(3) 0.467(4) 0.078(4) Uani 1 1 d . . . . .
H11 H 0.1738 1.0214 0.5465 0.093 Uiso 1 1 calc R U . . .
C12 C 0.1405(3) 1.0503(3) 0.272(4) 0.078(4) Uani 1 1 d . . . . .
F12 F 0.1667(2) 1.07357(18) 0.194(3) 0.112(3) Uani 1 1 d . . . . .
C13 C 0.1070(3) 1.0549(3) 0.156(4) 0.073(3) Uani 1 1 d . . . . .
H13 H 0.1013 1.0741 0.0244 0.088 Uiso 1 1 calc R U . . .
C14 C 0.0823(3) 1.0305(2) 0.238(3) 0.059(3) Uani 1 1 d . . . . .
H14 H 0.0590 1.0326 0.1554 0.071 Uiso 1 1 calc R U . . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
N1 C6 1.329(12) . ?
N1 C2 1.341(12) . ?
N1 Hg1 2.423(7) . ?
Hg1 I1 2.6252(7) . ?
Hg1 I2 2.6321(7) . ?
Hg1 I2 3.3097(8) 1_554 ?
I2 Hg1 3.3097(8) 1_556 ?
C2 C3 1.371(14) . ?
C2 H2 0.9500 . ?
C3 C4 1.378(14) . ?
C3 H3 0.9500 . ?
C4 C5 1.349(15) . ?
C4 C7 1.483(14) . ?
C5 C6 1.388(14) . ?
C5 H5 0.9500 . ?
C6 H6 0.9500 . ?
C7 N8 1.254(14) . ?
C7 H7 0.9500 . ?
N8 C9 1.411(12) . ?
C9 C14 1.375(15) . ?
C9 C10 1.390(14) . ?
C10 C11 1.392(15) . ?
C10 H10 0.9500 . ?
C11 C12 1.38(2) . ?
C11 H11 0.9500 . ?
C12 C13 1.367(18) . ?
C12 F12 1.367(12) . ?
C13 C14 1.366(14) . ?
C13 H13 0.9500 . ?
C14 H14 0.9500 . ?

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
C6 N1 C2 116.9(8) . . ?
C6 N1 Hg1 118.5(6) . . ?
C2 N1 Hg1 124.3(6) . . ?
N1 Hg1 I1 100.84(19) . . ?
N1 Hg1 I2 102.9(2) . . ?
I1 Hg1 I2 155.29(3) . . ?
N1 Hg1 I2 93.7(2) . 1_554 ?
I1 Hg1 I2 93.42(2) . 1_554 ?
I2 Hg1 I2 91.88(2) . 1_554 ?
Hg1 I2 Hg1 91.88(2) . 1_556 ?
N1 C2 C3 123.7(9) . . ?
N1 C2 H2 118.1 . . ?
C3 C2 H2 118.1 . . ?
C2 C3 C4 117.9(10) . . ?
C2 C3 H3 121.0 . . ?
C4 C3 H3 121.0 . . ?
C5 C4 C3 119.6(10) . . ?
C5 C4 C7 119.0(10) . . ?
C3 C4 C7 121.4(10) . . ?
C4 C5 C6 119.1(10) . . ?
C4 C5 H5 120.4 . . ?
C6 C5 H5 120.4 . . ?
N1 C6 C5 122.7(10) . . ?
N1 C6 H6 118.7 . . ?
C5 C6 H6 118.7 . . ?
N8 C7 C4 122.1(10) . . ?
N8 C7 H7 119.0 . . ?
C4 C7 H7 119.0 . . ?
C7 N8 C9 120.4(9) . . ?
C14 C9 C10 118.0(10) . . ?
C14 C9 N8 116.3(9) . . ?
C10 C9 N8 125.6(10) . . ?
C9 C10 C11 120.9(12) . . ?
C9 C10 H10 119.6 . . ?
C11 C10 H10 119.6 . . ?
C12 C11 C10 116.9(11) . . ?
C12 C11 H11 121.5 . . ?
C10 C11 H11 121.5 . . ?
C13 C12 F12 119.3(13) . . ?
C13 C12 C11 124.3(10) . . ?
F12 C12 C11 116.4(12) . . ?
C14 C13 C12 116.3(12) . . ?
C14 C13 H13 121.8 . . ?
C12 C13 H13 121.8 . . ?
C13 C14 C9 123.5(11) . . ?
C13 C14 H14 118.2 . . ?
C9 C14 H14 118.2 . . ?

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
C6 N1 C2 C3 -0.2(19) . . . . ?
Hg1 N1 C2 C3 -174.5(10) . . . . ?
N1 C2 C3 C4 2(2) . . . . ?
C2 C3 C4 C5 -2(2) . . . . ?
C2 C3 C4 C7 177.3(11) . . . . ?
C3 C4 C5 C6 1(2) . . . . ?
C7 C4 C5 C6 -178.1(12) . . . . ?
C2 N1 C6 C5 -0.7(19) . . . . ?
Hg1 N1 C6 C5 174.0(11) . . . . ?
C4 C5 C6 N1 0(2) . . . . ?
C5 C4 C7 N8 165.7(12) . . . . ?
C3 C4 C7 N8 -13.7(19) . . . . ?
C4 C7 N8 C9 -175.8(10) . . . . ?
C7 N8 C9 C14 -176.7(11) . . . . ?
C7 N8 C9 C10 7.1(17) . . . . ?
C14 C9 C10 C11 3.9(18) . . . . ?
N8 C9 C10 C11 -180.0(11) . . . . ?
C9 C10 C11 C12 -2.9(19) . . . . ?
C10 C11 C12 C13 1(2) . . . . ?
C10 C11 C12 F12 -178.5(12) . . . . ?
F12 C12 C13 C14 179.0(12) . . . . ?
C11 C12 C13 C14 -1(2) . . . . ?
C12 C13 C14 C9 2.0(19) . . . . ?
C10 C9 C14 C13 -3.5(17) . . . . ?
N8 C9 C14 C13 -180.0(11) . . . . ?

_refine_diff_density_max         0.630
_refine_diff_density_min         -0.536
_refine_diff_density_rms         0.093

_shelxl_version_number           2013-4



####################################################################### 
# 
# 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_6_lt
_database_code_depnum_ccdc_archive 'CCDC 1034451'
_audit_update_record             
;
2015-01-29 deposited with the CCDC.
2015-02-10 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2013
_chemical_name_systematic        
;
 ?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C12 H9 Cl Hg I2 N2'
_chemical_formula_sum            'C12 H9 Cl Hg I2 N2'
_chemical_formula_weight         671.05

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
I I -0.4742 1.8119 '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'

_space_group_crystal_system      orthorhombic
_space_group_IT_number           19
_space_group_name_H-M_alt        'P 21 21 21'
_space_group_name_Hall           'P 2ac 2ab'

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

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

_cell_length_a                   4.7590(2)
_cell_length_b                   16.9800(10)
_cell_length_c                   18.1555(7)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     1467.11(12)
_cell_formula_units_Z            4
_cell_measurement_temperature    100(1)
_cell_measurement_reflns_used    5153
_cell_measurement_theta_min      3.2750
_cell_measurement_theta_max      28.1200

_exptl_crystal_description       prism
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    3.038
_exptl_crystal_F_000             1192
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.4
_exptl_crystal_size_mid          0.1
_exptl_crystal_size_min          0.1
_exptl_absorpt_coefficient_mu    14.865
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_T_min  0.34233
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.32 (release 02-08-2013 CrysAlis171 .NET)
(compiled Aug  2 2013,16:46:58)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;

_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      100(1)
_diffrn_radiation_wavelength     0.7107
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_source         'Enhance (Mo) X-ray Source'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Xcalibur, Eos'
_diffrn_detector_area_resol_mean 16.1544
_diffrn_measurement_method       ω-scan
_diffrn_reflns_number            10372
_diffrn_reflns_av_unetI/netI     0.0776
_diffrn_reflns_av_R_equivalents  0.1119
_diffrn_reflns_limit_h_min       -5
_diffrn_reflns_limit_h_max       5
_diffrn_reflns_limit_k_min       -20
_diffrn_reflns_limit_k_max       19
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_theta_min         3.285
_diffrn_reflns_theta_max         24.994
_diffrn_reflns_theta_full        25.000
_diffrn_measured_fraction_theta_max 0.992
_diffrn_measured_fraction_theta_full 0.992
_diffrn_reflns_Laue_measured_fraction_max 0.992
_diffrn_reflns_Laue_measured_fraction_full 0.992
_diffrn_reflns_point_group_measured_fraction_max 0.995
_diffrn_reflns_point_group_measured_fraction_full 0.995
_reflns_number_total             2582
_reflns_number_gt                2517
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.679
_reflns_Friedel_fraction_max     0.999
_reflns_Friedel_fraction_full    0.999

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

_computing_data_collection       'CrysAlis Pro (Agilent Technologies (2011))'
_computing_cell_refinement       'CrysAlis Pro (Agilent Technologies (2011))'
_computing_data_reduction        'CrysAlis Pro (Agilent Technologies (2011))'
_computing_structure_solution    'SIR92 (Altomare et al., 1993)'
_computing_structure_refinement  'SHELXL-2013 (Sheldrick, 2013)'
_computing_molecular_graphics    'Mercury (MacRae et al., 2009)'
_computing_publication_material  'SHELXL-2013 (Sheldrick, 2013)'

_refine_special_details          
;
ISOR restraints were aplied for C and N atoms, in order to avoid wxcentric 
shapes of the ellipsoids
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0700P)²+3.6416P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_abs_structure_details 
;
 Flack x determined using 944 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons and Flack (2004), Acta Cryst. A60, s61).
;
_refine_ls_abs_structure_Flack   0.003(6)
_chemical_absolute_configuration ?
_refine_ls_number_reflns         2582
_refine_ls_number_parameters     163
_refine_ls_number_restraints     84
_refine_ls_R_factor_all          0.0500
_refine_ls_R_factor_gt           0.0490
_refine_ls_wR_factor_ref         0.1064
_refine_ls_wR_factor_gt          0.1052
_refine_ls_goodness_of_fit_ref   0.977
_refine_ls_restrained_S_all      0.966
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
N1 N 0.697(3) 0.9514(7) 0.4573(8) 0.016(3) Uani 1 1 d . U . . .
Hg1 Hg 1.01355(12) 0.86089(3) 0.51926(3) 0.0146(2) Uani 1 1 d . . . . .
I1 I 1.1140(2) 0.93444(6) 0.64401(6) 0.0179(3) Uani 1 1 d . . . . .
I2 I 1.1335(2) 0.77117(6) 0.40403(6) 0.0150(3) Uani 1 1 d . . . . .
C2 C 0.572(3) 1.0089(8) 0.4976(10) 0.015(3) Uani 1 1 d . U . . .
H2 H 0.6209 1.0146 0.5481 0.018 Uiso 1 1 calc R U . . .
C3 C 0.374(3) 1.0596(9) 0.4678(9) 0.015(3) Uani 1 1 d . U . . .
H3 H 0.2934 1.0998 0.4975 0.018 Uiso 1 1 calc R U . . .
C4 C 0.297(3) 1.0520(8) 0.3972(9) 0.012(3) Uani 1 1 d . U . . .
C5 C 0.425(3) 0.9953(9) 0.3547(10) 0.018(4) Uani 1 1 d . U . . .
H5 H 0.3814 0.9902 0.3038 0.021 Uiso 1 1 calc R U . . .
C6 C 0.622(3) 0.9448(9) 0.3886(10) 0.016(3) Uani 1 1 d . U . . .
H6 H 0.7036 0.9040 0.3599 0.020 Uiso 1 1 calc R U . . .
C7 C 0.092(3) 1.1038(9) 0.3624(10) 0.016(3) Uani 1 1 d . U . . .
H7 H 0.0578 1.1007 0.3109 0.019 Uiso 1 1 calc R U . . .
N8 N -0.046(3) 1.1547(7) 0.4030(8) 0.014(3) Uani 1 1 d . U . . .
C9 C -0.252(3) 1.2050(8) 0.3719(9) 0.012(3) Uani 1 1 d . U . . .
C10 C -0.345(3) 1.2058(8) 0.3001(9) 0.014(3) Uani 1 1 d . U . . .
H10 H -0.2690 1.1686 0.2665 0.017 Uiso 1 1 calc R U . . .
C11 C -0.543(3) 1.2586(9) 0.2751(10) 0.017(4) Uani 1 1 d . U . . .
H11 H -0.6039 1.2583 0.2253 0.021 Uiso 1 1 calc R U . . .
C12 C -0.651(3) 1.3128(8) 0.3261(9) 0.012(3) Uani 1 1 d . U . . .
Cl12 Cl -0.9013(8) 1.3816(2) 0.2972(2) 0.0190(9) Uani 1 1 d . . . . .
C13 C -0.567(3) 1.3133(9) 0.3984(10) 0.018(4) Uani 1 1 d . U . . .
H13 H -0.6434 1.3502 0.4324 0.021 Uiso 1 1 calc R U . . .
C14 C -0.369(3) 1.2590(8) 0.4206(9) 0.010(3) Uani 1 1 d . U . . .
H14 H -0.3115 1.2583 0.4707 0.012 Uiso 1 1 calc R U . . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
N1 C6 1.30(2) . ?
N1 C2 1.36(2) . ?
N1 Hg1 2.427(13) . ?
Hg1 I1 2.6303(12) . ?
Hg1 I2 2.6502(12) . ?
Hg1 I2 3.1998(11) 3_466 ?
I2 Hg1 3.1998(11) 3_566 ?
C2 C3 1.38(2) . ?
C3 C4 1.34(2) . ?
C4 C5 1.38(2) . ?
C4 C7 1.46(2) . ?
C5 C6 1.41(2) . ?
C7 N8 1.31(2) . ?
N8 C9 1.42(2) . ?
C9 C10 1.38(2) . ?
C9 C14 1.39(2) . ?
C10 C11 1.38(2) . ?
C11 C12 1.40(2) . ?
C12 C13 1.37(2) . ?
C12 Cl12 1.748(15) . ?
C13 C14 1.38(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
C6 N1 C2 117.1(15) . . ?
C6 N1 Hg1 124.1(11) . . ?
C2 N1 Hg1 118.6(12) . . ?
N1 Hg1 I1 102.2(3) . . ?
N1 Hg1 I2 97.6(4) . . ?
I1 Hg1 I2 155.99(4) . . ?
N1 Hg1 I2 107.2(3) . 3_466 ?
I1 Hg1 I2 93.48(3) . 3_466 ?
I2 Hg1 I2 93.58(3) . 3_466 ?
Hg1 I2 Hg1 100.43(4) . 3_566 ?
N1 C2 C3 122.4(17) . . ?
C4 C3 C2 120.0(15) . . ?
C3 C4 C5 118.9(15) . . ?
C3 C4 C7 122.6(15) . . ?
C5 C4 C7 118.4(16) . . ?
C4 C5 C6 118.3(17) . . ?
N1 C6 C5 123.3(15) . . ?
N8 C7 C4 119.3(17) . . ?
C7 N8 C9 121.2(16) . . ?
C10 C9 C14 117.8(14) . . ?
C10 C9 N8 127.3(15) . . ?
C14 C9 N8 115.0(15) . . ?
C9 C10 C11 122.6(15) . . ?
C10 C11 C12 117.4(16) . . ?
C13 C12 C11 121.9(14) . . ?
C13 C12 Cl12 118.7(12) . . ?
C11 C12 Cl12 119.4(13) . . ?
C12 C13 C14 118.3(15) . . ?
C13 C14 C9 122.0(16) . . ?

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
C6 N1 C2 C3 -1(2) . . . . ?
Hg1 N1 C2 C3 -175.5(11) . . . . ?
N1 C2 C3 C4 1(2) . . . . ?
C2 C3 C4 C5 -2(2) . . . . ?
C2 C3 C4 C7 -179.6(14) . . . . ?
C3 C4 C5 C6 3(2) . . . . ?
C7 C4 C5 C6 -179.5(13) . . . . ?
C2 N1 C6 C5 2(2) . . . . ?
Hg1 N1 C6 C5 176.1(11) . . . . ?
C4 C5 C6 N1 -3(2) . . . . ?
C3 C4 C7 N8 -7(2) . . . . ?
C5 C4 C7 N8 175.5(14) . . . . ?
C4 C7 N8 C9 -178.6(12) . . . . ?
C7 N8 C9 C10 3(2) . . . . ?
C7 N8 C9 C14 -176.6(13) . . . . ?
C14 C9 C10 C11 1(2) . . . . ?
N8 C9 C10 C11 -178.6(14) . . . . ?
C9 C10 C11 C12 0(2) . . . . ?
C10 C11 C12 C13 -1(2) . . . . ?
C10 C11 C12 Cl12 179.5(11) . . . . ?
C11 C12 C13 C14 0(2) . . . . ?
Cl12 C12 C13 C14 -179.8(11) . . . . ?
C12 C13 C14 C9 1(2) . . . . ?
C10 C9 C14 C13 -2(2) . . . . ?
N8 C9 C14 C13 178.3(13) . . . . ?


_refine_diff_density_max         3.476
_refine_diff_density_min         -3.182
_refine_diff_density_rms         0.461

_shelxl_version_number           2013-4



####################################################################### 
# 
# 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_7
_database_code_depnum_ccdc_archive 'CCDC 1034452'
_audit_update_record             
;
2015-01-29 deposited with the CCDC.
2015-02-10 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2013
_chemical_name_systematic        
;
 ?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C12 H9 Br Hg I2 N2'
_chemical_formula_sum            'C12 H9 Br Hg I2 N2'
_chemical_formula_weight         715.51

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'
I I -0.4742 1.8119 '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'

_space_group_crystal_system      orthorhombic
_space_group_IT_number           33
_space_group_name_H-M_alt        'P n a 21'
_space_group_name_Hall           'P 2c -2n'

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

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

_cell_length_a                   16.3554(7)
_cell_length_b                   22.6143(7)
_cell_length_c                   4.2385(2)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     1567.68(11)
_cell_formula_units_Z            4
_cell_measurement_temperature    100(1)
_cell_measurement_reflns_used    1724
_cell_measurement_theta_min      4.1390
_cell_measurement_theta_max      27.3970

_exptl_crystal_description       prism
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    3.032
_exptl_crystal_F_000             1264
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.35
_exptl_crystal_size_mid          0.07
_exptl_crystal_size_min          0.07
_exptl_absorpt_coefficient_mu    16.290
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_T_min  0.44488
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.32 (release 02-08-2013 CrysAlis171 .NET)
(compiled Aug  2 2013,16:46:58)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;

_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      100(1)
_diffrn_radiation_wavelength     0.7107
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_source         'Enhance (Mo) X-ray Source'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Xcalibur, Eos'
_diffrn_detector_area_resol_mean 16.1544
_diffrn_measurement_method       ω-scan
_diffrn_reflns_number            4914
_diffrn_reflns_av_unetI/netI     0.0622
_diffrn_reflns_av_R_equivalents  0.0356
_diffrn_reflns_limit_h_min       -21
_diffrn_reflns_limit_h_max       21
_diffrn_reflns_limit_k_min       -27
_diffrn_reflns_limit_k_max       23
_diffrn_reflns_limit_l_min       -3
_diffrn_reflns_limit_l_max       5
_diffrn_reflns_theta_min         2.975
_diffrn_reflns_theta_max         28.255
_diffrn_reflns_theta_full        25.000
_diffrn_measured_fraction_theta_max 0.859
_diffrn_measured_fraction_theta_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.859
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.630
_diffrn_reflns_point_group_measured_fraction_full 0.764
_reflns_number_total             2459
_reflns_number_gt                2229
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.297
_reflns_Friedel_fraction_max     0.332
_reflns_Friedel_fraction_full    0.450

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

_computing_data_collection       'CrysAlis Pro (Agilent Technologies (2011))'
_computing_cell_refinement       'CrysAlis Pro (Agilent Technologies (2011))'
_computing_data_reduction        'CrysAlis Pro (Agilent Technologies (2011))'
_computing_structure_solution    'SIR92 (Altomare et al., 1993)'
_computing_structure_refinement  'SHELXL-2013 (Sheldrick, 2013)'
_computing_molecular_graphics    'Mercury (MacRae et al., 2009)'
_computing_publication_material  'SHELXL-2013 (Sheldrick, 2013)'

_refine_special_details          
;
ISOR restraints were aplied for two C atoms, in order to avoid wxcentric 
shapes of the ellipsoids
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0100P)²] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_abs_structure_details 
;
 Classical Flack method preferred over Parsons because s.u. lower.
;
_refine_ls_abs_structure_Flack   0.013(9)
_chemical_absolute_configuration ?
_refine_ls_number_reflns         2459
_refine_ls_number_parameters     163
_refine_ls_number_restraints     13
_refine_ls_R_factor_all          0.0354
_refine_ls_R_factor_gt           0.0296
_refine_ls_wR_factor_ref         0.0487
_refine_ls_wR_factor_gt          0.0454
_refine_ls_goodness_of_fit_ref   0.940
_refine_ls_restrained_S_all      0.938
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
N1 N 0.5441(5) -0.2096(4) 0.046(2) 0.020(2) Uani 1 1 d . . . . .
Hg1 Hg 0.48129(3) -0.11223(2) 0.06229(13) 0.02002(12) Uani 1 1 d . . . . .
I1 I 0.34252(5) -0.13486(3) 0.35774(19) 0.02342(19) Uani 1 1 d . . . . .
I2 I 0.57907(4) -0.05967(3) -0.35242(16) 0.01706(17) Uani 1 1 d . . . . .
C2 C 0.6134(7) -0.2200(5) -0.100(3) 0.021(3) Uani 1 1 d . . . . .
H2 H 0.6430 -0.1870 -0.1792 0.025 Uiso 1 1 calc R U . . .
C3 C 0.6467(7) -0.2762(5) -0.148(3) 0.023(3) Uani 1 1 d . . . . .
H3 H 0.6958 -0.2812 -0.2642 0.027 Uiso 1 1 calc R U . . .
C4 C 0.6059(7) -0.3248(5) -0.019(2) 0.020(3) Uani 1 1 d . . . . .
C5 C 0.5325(7) -0.3131(5) 0.138(3) 0.022(3) Uani 1 1 d . . . . .
H5 H 0.5014 -0.3448 0.2223 0.026 Uiso 1 1 calc R U . . .
C6 C 0.5048(7) -0.2559(5) 0.171(3) 0.021(3) Uani 1 1 d . . . . .
H6 H 0.4560 -0.2491 0.2873 0.025 Uiso 1 1 calc R U . . .
C7 C 0.6358(7) -0.3858(5) -0.067(3) 0.021(3) Uani 1 1 d . . . . .
H7 H 0.6824 -0.3921 -0.1971 0.026 Uiso 1 1 calc R U . . .
N8 N 0.6026(5) -0.4285(4) 0.055(2) 0.022(2) Uani 1 1 d . . . . .
C9 C 0.6318(7) -0.4871(5) 0.004(3) 0.020(3) Uani 1 1 d . . . . .
C10 C 0.6997(6) -0.5017(5) -0.186(3) 0.019(3) Uani 1 1 d . . . . .
H10 H 0.7305 -0.4712 -0.2841 0.023 Uiso 1 1 calc R U . . .
C11 C 0.7216(7) -0.5600(5) -0.231(3) 0.019(3) Uani 1 1 d . U . . .
H11 H 0.7666 -0.5704 -0.3617 0.023 Uiso 1 1 calc R U . . .
C12 C 0.6752(7) -0.6033(5) -0.077(3) 0.020(3) Uani 1 1 d . . . . .
Br12 Br 0.70418(7) -0.68430(5) -0.1492(3) 0.0257(3) Uani 1 1 d . . . . .
C13 C 0.6093(6) -0.5909(5) 0.110(3) 0.022(3) Uani 1 1 d . U . . .
H13 H 0.5795 -0.6214 0.2134 0.026 Uiso 1 1 calc R U . . .
C14 C 0.5881(7) -0.5319(5) 0.143(3) 0.022(3) Uani 1 1 d . . . . .
H14 H 0.5415 -0.5221 0.2669 0.027 Uiso 1 1 calc R U . . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
N1 C2 1.313(13) . ?
N1 C6 1.338(13) . ?
N1 Hg1 2.431(9) . ?
Hg1 I1 2.6422(9) . ?
Hg1 I2 2.6570(8) . ?
Hg1 I2 3.1819(9) 1_556 ?
I2 Hg1 3.1818(9) 1_554 ?
C2 C3 1.396(14) . ?
C3 C4 1.396(15) . ?
C4 C5 1.399(15) . ?
C4 C7 1.478(15) . ?
C5 C6 1.377(15) . ?
C7 N8 1.221(13) . ?
N8 C9 1.425(13) . ?
C9 C14 1.373(15) . ?
C9 C10 1.413(14) . ?
C10 C11 1.380(14) . ?
C11 C12 1.399(14) . ?
C12 C13 1.370(15) . ?
C12 Br12 1.916(11) . ?
C13 C14 1.386(14) . ?

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 N1 C6 117.5(10) . . ?
C2 N1 Hg1 122.7(8) . . ?
C6 N1 Hg1 119.6(7) . . ?
N1 Hg1 I1 101.6(2) . . ?
N1 Hg1 I2 97.6(2) . . ?
I1 Hg1 I2 156.52(3) . . ?
N1 Hg1 I2 98.5(2) . 1_556 ?
I1 Hg1 I2 97.74(3) . 1_556 ?
I2 Hg1 I2 92.65(2) . 1_556 ?
Hg1 I2 Hg1 92.65(2) . 1_554 ?
N1 C2 C3 124.6(11) . . ?
C4 C3 C2 118.3(11) . . ?
C3 C4 C5 116.5(11) . . ?
C3 C4 C7 121.6(10) . . ?
C5 C4 C7 121.8(11) . . ?
C6 C5 C4 120.6(11) . . ?
N1 C6 C5 122.4(11) . . ?
N8 C7 C4 122.2(11) . . ?
C7 N8 C9 121.5(10) . . ?
C14 C9 C10 118.9(10) . . ?
C14 C9 N8 116.6(10) . . ?
C10 C9 N8 124.5(10) . . ?
C11 C10 C9 120.4(11) . . ?
C10 C11 C12 117.6(11) . . ?
C13 C12 C11 123.7(11) . . ?
C13 C12 Br12 118.9(9) . . ?
C11 C12 Br12 117.4(8) . . ?
C12 C13 C14 116.9(11) . . ?
C9 C14 C13 122.4(11) . . ?

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
C6 N1 C2 C3 3.4(18) . . . . ?
Hg1 N1 C2 C3 -172.0(9) . . . . ?
N1 C2 C3 C4 -3.1(19) . . . . ?
C2 C3 C4 C5 2.4(17) . . . . ?
C2 C3 C4 C7 178.1(11) . . . . ?
C3 C4 C5 C6 -2.3(16) . . . . ?
C7 C4 C5 C6 -178.1(11) . . . . ?
C2 N1 C6 C5 -3.2(17) . . . . ?
Hg1 N1 C6 C5 172.3(9) . . . . ?
C4 C5 C6 N1 2.8(18) . . . . ?
C3 C4 C7 N8 176.9(12) . . . . ?
C5 C4 C7 N8 -7.6(18) . . . . ?
C4 C7 N8 C9 179.5(10) . . . . ?
C7 N8 C9 C14 -177.7(11) . . . . ?
C7 N8 C9 C10 -0.3(18) . . . . ?
C14 C9 C10 C11 -0.1(17) . . . . ?
N8 C9 C10 C11 -177.4(11) . . . . ?
C9 C10 C11 C12 -1.1(17) . . . . ?
C10 C11 C12 C13 0.8(18) . . . . ?
C10 C11 C12 Br12 178.5(9) . . . . ?
C11 C12 C13 C14 0.7(17) . . . . ?
Br12 C12 C13 C14 -176.9(9) . . . . ?
C10 C9 C14 C13 1.7(18) . . . . ?
N8 C9 C14 C13 179.3(11) . . . . ?
C12 C13 C14 C9 -2.0(18) . . . . ?

_refine_diff_density_max         1.414
_refine_diff_density_min         -1.374
_refine_diff_density_rms         0.229

_shelxl_version_number           2013-4



####################################################################### 
# 
# 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_8lt
_database_code_depnum_ccdc_archive 'CCDC 1034453'
_audit_update_record             
;
2015-01-29 deposited with the CCDC.
2015-02-10 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2013
_chemical_name_systematic        
;
 ?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C12 H9 Hg I3 N2'
_chemical_formula_sum            'C12 H9 Hg I3 N2'
_chemical_formula_weight         762.50

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'
N N 0.0061 0.0033 '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'
Hg Hg -2.3894 9.2266 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 21/c'
_space_group_name_Hall           '-P 2ybc'

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

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

_cell_length_a                   4.2727(2)
_cell_length_b                   24.0248(8)
_cell_length_c                   15.4948(5)
_cell_angle_alpha                90
_cell_angle_beta                 95.495(3)
_cell_angle_gamma                90
_cell_volume                     1583.24(10)
_cell_formula_units_Z            4
_cell_measurement_temperature    100(1)
_cell_measurement_reflns_used    8077
_cell_measurement_theta_min      3.3840
_cell_measurement_theta_max      28.1730

_exptl_crystal_description       prism
_exptl_crystal_colour            pale-yellow
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    3.199
_exptl_crystal_F_000             1336
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.1
_exptl_absorpt_coefficient_mu    15.556
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_T_min  0.21300
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;

_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      100(1)
_diffrn_radiation_wavelength     0.7107
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_source         'Enhance (Mo) X-ray Source'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Xcalibur, Eos'
_diffrn_detector_area_resol_mean 16.1544
_diffrn_measurement_method       ω-scan
_diffrn_reflns_number            16613
_diffrn_reflns_av_unetI/netI     0.0203
_diffrn_reflns_av_R_equivalents  0.0483
_diffrn_reflns_limit_h_min       -5
_diffrn_reflns_limit_h_max       5
_diffrn_reflns_limit_k_min       -28
_diffrn_reflns_limit_k_max       28
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_theta_min         2.774
_diffrn_reflns_theta_max         24.998
_diffrn_reflns_theta_full        25.000
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measured_fraction_theta_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_point_group_measured_fraction_full 0.999
_reflns_number_total             4894
_reflns_number_gt                4572
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_reflns_special_details          
;
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;

_computing_data_collection       'CrysAlis Pro (Agilent Technologies (2011))'
_computing_cell_refinement       'CrysAlis Pro (Agilent Technologies (2011))'
_computing_data_reduction        'CrysAlis Pro (Agilent Technologies (2011))'
_computing_structure_solution    'SIR92 (Altomare et al., 1993)'
_computing_structure_refinement  'SHELXL-2013 (Sheldrick, 2013)'
_computing_molecular_graphics    'Mercury (MacRae et al., 2009)'
_computing_publication_material  'SHELXL-2013 (Sheldrick, 2013)'

_refine_special_details          
;
Refined as a 2-component twin.
High residual density peaks are observed close to Hg atom (around 0.9A)
ISOR restraints were aplied for two C atoms, in order to avoid wxcentric 
shapes of the ellipsoids
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0995P)²+4.8940P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         4894
_refine_ls_number_parameters     164
_refine_ls_number_restraints     12
_refine_ls_R_factor_all          0.0615
_refine_ls_R_factor_gt           0.0587
_refine_ls_wR_factor_ref         0.1631
_refine_ls_wR_factor_gt          0.1609
_refine_ls_goodness_of_fit_ref   1.356
_refine_ls_restrained_S_all      1.355
_refine_ls_shift/su_max          0.004
_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_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
N1 N 0.734(3) 0.1907(6) 1.0768(8) 0.016(3) Uani 1 1 d . . . . .
Hg1 Hg 0.71096(15) 0.25283(2) 1.19823(4) 0.0170(2) Uani 1 1 d . . . . .
I1 I 0.3032(3) 0.32885(4) 1.13617(7) 0.0194(3) Uani 1 1 d . . . . .
I2 I 1.0900(2) 0.20337(4) 1.31798(6) 0.0153(3) Uani 1 1 d . . . . .
C2 C 0.600(4) 0.2031(7) 0.9986(11) 0.020(4) Uani 1 1 d . . . . .
H2 H 0.4807 0.2364 0.9912 0.023 Uiso 1 1 calc R U . . .
C3 C 0.626(4) 0.1699(7) 0.9278(11) 0.023(4) Uani 1 1 d . . . . .
H3 H 0.5180 0.1797 0.8735 0.027 Uiso 1 1 calc R U . . .
C4 C 0.809(4) 0.1223(7) 0.9350(10) 0.017(3) Uani 1 1 d . . . . .
C5 C 0.952(4) 0.1096(6) 1.0182(11) 0.020(4) Uani 1 1 d . . . . .
H5 H 1.0772 0.0771 1.0275 0.024 Uiso 1 1 calc R U . . .
C6 C 0.908(4) 0.1447(7) 1.0855(11) 0.025(4) Uani 1 1 d . U . . .
H6 H 1.0071 0.1358 1.1413 0.030 Uiso 1 1 calc R U . . .
C7 C 0.862(4) 0.0884(6) 0.8594(10) 0.019(4) Uani 1 1 d . . . . .
H7 H 0.7353 0.0947 0.8065 0.023 Uiso 1 1 calc R U . . .
N8 N 1.069(3) 0.0510(5) 0.8623(8) 0.018(3) Uani 1 1 d . . . . .
C9 C 1.130(4) 0.0194(7) 0.7875(11) 0.018(3) Uani 1 1 d . . . . .
C10 C 1.328(4) -0.0251(7) 0.8036(9) 0.016(3) Uani 1 1 d . U . . .
H10 H 1.4130 -0.0333 0.8611 0.019 Uiso 1 1 calc R U . . .
C11 C 1.405(4) -0.0583(7) 0.7341(11) 0.022(4) Uani 1 1 d . . . . .
H11 H 1.5345 -0.0902 0.7446 0.026 Uiso 1 1 calc R U . . .
C12 C 1.290(4) -0.0444(7) 0.6497(10) 0.016(3) Uani 1 1 d . . . . .
I12 I 1.4170(2) -0.09022(4) 0.54431(6) 0.0163(3) Uani 1 1 d . . . . .
C13 C 1.090(4) 0.0014(6) 0.6350(10) 0.013(3) Uani 1 1 d . . . . .
H13 H 1.0106 0.0109 0.5775 0.015 Uiso 1 1 calc R U . . .
C14 C 1.009(4) 0.0325(7) 0.7037(11) 0.020(4) Uani 1 1 d . . . . .
H14 H 0.8703 0.0632 0.6938 0.024 Uiso 1 1 calc R U . . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
N1 C2 1.32(2) . ?
N1 C6 1.33(2) . ?
N1 Hg1 2.410(13) . ?
Hg1 I2 2.6273(11) . ?
Hg1 I1 2.6408(12) . ?
C2 C3 1.37(2) . ?
C3 C4 1.38(2) . ?
C4 C5 1.41(2) . ?
C4 C7 1.46(2) . ?
C5 C6 1.37(2) . ?
C7 N8 1.26(2) . ?
N8 C9 1.43(2) . ?
C9 C10 1.37(2) . ?
C9 C14 1.39(2) . ?
C10 C11 1.40(2) . ?
C11 C12 1.39(2) . ?
C12 C13 1.40(2) . ?
C12 I12 2.085(15) . ?
C13 C14 1.37(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 N1 C6 117.8(14) . . ?
C2 N1 Hg1 122.0(11) . . ?
C6 N1 Hg1 119.9(11) . . ?
N1 Hg1 I2 101.7(3) . . ?
N1 Hg1 I1 102.6(3) . . ?
I2 Hg1 I1 155.57(4) . . ?
N1 C2 C3 122.9(16) . . ?
C2 C3 C4 120.4(16) . . ?
C3 C4 C5 116.5(14) . . ?
C3 C4 C7 121.8(15) . . ?
C5 C4 C7 121.7(15) . . ?
C6 C5 C4 119.1(15) . . ?
N1 C6 C5 123.4(16) . . ?
N8 C7 C4 122.2(15) . . ?
C7 N8 C9 122.2(14) . . ?
C10 C9 C14 121.0(15) . . ?
C10 C9 N8 115.1(15) . . ?
C14 C9 N8 123.8(15) . . ?
C9 C10 C11 119.3(14) . . ?
C12 C11 C10 119.8(15) . . ?
C11 C12 C13 119.9(14) . . ?
C11 C12 I12 120.9(12) . . ?
C13 C12 I12 119.3(11) . . ?
C14 C13 C12 119.8(15) . . ?
C13 C14 C9 120.2(15) . . ?

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
C6 N1 C2 C3 2(3) . . . . ?
Hg1 N1 C2 C3 176.0(13) . . . . ?
N1 C2 C3 C4 -3(3) . . . . ?
C2 C3 C4 C5 2(3) . . . . ?
C2 C3 C4 C7 -175.2(16) . . . . ?
C3 C4 C5 C6 -1(3) . . . . ?
C7 C4 C5 C6 176.3(17) . . . . ?
C2 N1 C6 C5 -1(3) . . . . ?
Hg1 N1 C6 C5 -175.0(14) . . . . ?
C4 C5 C6 N1 0(3) . . . . ?
C3 C4 C7 N8 167.3(17) . . . . ?
C5 C4 C7 N8 -10(3) . . . . ?
C4 C7 N8 C9 -177.2(15) . . . . ?
C7 N8 C9 C10 -170.7(16) . . . . ?
C7 N8 C9 C14 11(3) . . . . ?
C14 C9 C10 C11 -1(2) . . . . ?
N8 C9 C10 C11 -179.3(14) . . . . ?
C9 C10 C11 C12 3(2) . . . . ?
C10 C11 C12 C13 -2(2) . . . . ?
C10 C11 C12 I12 176.8(12) . . . . ?
C11 C12 C13 C14 0(2) . . . . ?
I12 C12 C13 C14 -178.8(12) . . . . ?
C12 C13 C14 C9 1(2) . . . . ?
C10 C9 C14 C13 -1(3) . . . . ?
N8 C9 C14 C13 177.2(15) . . . . ?

_refine_diff_density_max         2.185
_refine_diff_density_min         -3.003
_refine_diff_density_rms         0.417

_shelxl_version_number           2013-4



