# Electronic Supplementary Material (ESI) for CrystEngComm.
# This journal is © The Royal Society of Chemistry 2016

####################################################################### 
# 
# 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_001-Br
_database_code_depnum_ccdc_archive 'CCDC 1485718'
_audit_update_record             
;
2016-06-15 deposited with the CCDC.
2016-08-12 downloaded from the CCDC.
;
# start Validation Reply Form
_vrf_PLAT972_001-Br              
;
PROBLEM: Check Calcd Residual Density  0.91A From     Hg1      -3.79 eA-3
RESPONSE: As the large negative (-3.79 eA-3) difference Fourier peak is located at short distance from Hg1 (0.91 A), the peak is a ghost of the  heavy Hg atom.
;
_vrf_PLAT971_001-Br              
;
PROBLEM: Check Calcd Residual Density  0.96A From     Hg1       2.57 eA-3
RESPONSE: As the large negative (2.57 eA-3) difference Fourier peak is located at short distance from Hg1 (0.96 A), the peak is a ghost of the  heavy Hg atom.
;
_vrf_PLAT972_001-Br_2            
;
PROBLEM: Check Calcd Residual Density  0.96A From     Hg1      -2.82 eA-3
RESPONSE: As the large negative (-2.82 eA-3) difference Fourier peak is located at short distance from Hg1 (0.96 A), the peak is a ghost of the  heavy Hg atom.
;
# Added during the CSD deposition process: Wednesday 15 June 2016 08:59 AM
# end Validation Reply Form


_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C14 H20 Br2 Hg N2 Si2'
_chemical_formula_weight         632.91

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'
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'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Si Si 0.0817 0.0704 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      monoclinic
_space_group_IT_number           13
_space_group_name_H-M_alt        'P 2/n'
_space_group_name_Hall           '-P 2yac'

_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, -y, -z'
'x-1/2, -y, z-1/2'

_cell_length_a                   11.2748(2)
_cell_length_b                   6.65010(10)
_cell_length_c                   14.1700(2)
_cell_angle_alpha                90
_cell_angle_beta                 108.5960(10)
_cell_angle_gamma                90
_cell_volume                     1006.98(3)
_cell_formula_units_Z            2
_cell_measurement_temperature    173(2)
_cell_measurement_reflns_used    5180
_cell_measurement_theta_min      2.79
_cell_measurement_theta_max      27.77

_exptl_crystal_description       block
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    2.087
_exptl_crystal_F_000             592
_exptl_transmission_factor_min   0.065
_exptl_transmission_factor_max   0.096
_exptl_crystal_size_max          0.410
_exptl_crystal_size_mid          0.210
_exptl_crystal_size_min          0.200
_exptl_absorpt_coefficient_mu    11.725
_shelx_estimated_absorpt_T_min   0.086
_shelx_estimated_absorpt_T_max   0.203
_exptl_absorpt_correction_type   Multi-scan
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   SADABS
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      173(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruker Breeze CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            15469
_diffrn_reflns_av_unetI/netI     0.0821
_diffrn_reflns_av_R_equivalents  0.2003
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_theta_min         2.022
_diffrn_reflns_theta_max         26.498
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measured_fraction_theta_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 1.000
_diffrn_reflns_point_group_measured_fraction_full 1.000
_reflns_number_total             2105
_reflns_number_gt                1827
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_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       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0629P)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_number_reflns         2105
_refine_ls_number_parameters     114
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0509
_refine_ls_R_factor_gt           0.0468
_refine_ls_wR_factor_ref         0.1113
_refine_ls_wR_factor_gt          0.1097
_refine_ls_goodness_of_fit_ref   1.008
_refine_ls_restrained_S_all      1.008
_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
Hg1 Hg 0.7500 -0.32388(5) 0.2500 0.03094(16) Uani 1 2 d S T P . .
Br1 Br 0.65195(7) -0.47498(11) 0.36818(5) 0.0374(2) Uani 1 1 d . . . . .
Si1 Si 0.23563(18) 0.0263(4) 0.16562(13) 0.0480(6) Uani 1 1 d . . . . .
N1 N 0.6006(5) -0.0715(9) 0.1754(4) 0.0316(12) Uani 1 1 d . . . . .
C1 C 0.4863(6) -0.0827(9) 0.1847(4) 0.0253(12) Uani 1 1 d . . . . .
H1A H 0.4679 -0.1948 0.2193 0.030 Uiso 1 1 calc R U . . .
C2 C 0.3936(6) 0.0583(10) 0.1473(4) 0.0295(14) Uani 1 1 d . . . . .
C3 C 0.4238(9) 0.2197(11) 0.0965(5) 0.046(2) Uani 1 1 d . . . . .
H3A H 0.3629 0.3203 0.0685 0.056 Uiso 1 1 calc R U . . .
C4 C 0.5411(8) 0.2350(13) 0.0863(5) 0.047(2) Uani 1 1 d . . . . .
H4A H 0.5618 0.3459 0.0523 0.056 Uiso 1 1 calc R U . . .
C5 C 0.6285(8) 0.0855(13) 0.1267(5) 0.0450(19) Uani 1 1 d . . . . .
H5A H 0.7094 0.0945 0.1197 0.054 Uiso 1 1 calc R U . . .
C6 C 0.1670(16) 0.317(2) 0.1356(10) 0.036(3) Uani 0.5 1 d . . P A 1
H6A H 0.2172 0.4079 0.1874 0.043 Uiso 0.5 1 calc R U P A 1
H6B H 0.1716 0.3595 0.0707 0.043 Uiso 0.5 1 calc R U P A 1
H6C H 0.0797 0.3205 0.1346 0.043 Uiso 0.5 1 calc R U P A 1
C7 C 0.1483(15) -0.131(2) 0.0756(11) 0.041(3) Uani 0.5 1 d . . P A 1
H7A H 0.0659 -0.1494 0.0838 0.049 Uiso 0.5 1 calc R U P A 1
H7B H 0.1380 -0.0725 0.0100 0.049 Uiso 0.5 1 calc R U P A 1
H7C H 0.1905 -0.2612 0.0812 0.049 Uiso 0.5 1 calc R U P A 1
C6' C 0.1063(14) 0.1644(18) 0.0897(10) 0.031(3) Uani 0.5 1 d . . P A 2
H6'A H 0.0318 0.1317 0.1081 0.037 Uiso 0.5 1 calc R U P A 2
H6'B H 0.1238 0.3087 0.0993 0.037 Uiso 0.5 1 calc R U P A 2
H6'C H 0.0915 0.1295 0.0197 0.037 Uiso 0.5 1 calc R U P A 2
C7' C 0.1906(12) -0.2771(19) 0.1342(9) 0.026(3) Uani 0.5 1 d . . P A 2
H7'A H 0.2595 -0.3613 0.1745 0.031 Uiso 0.5 1 calc R U P A 2
H7'B H 0.1142 -0.3093 0.1500 0.031 Uiso 0.5 1 calc R U P A 2
H7'C H 0.1769 -0.3028 0.0634 0.031 Uiso 0.5 1 calc R U P A 2


_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 2.374(5) 2_655 ?
Hg1 N1 2.374(5) . ?
Hg1 Br1 2.4934(6) . ?
Hg1 Br1 2.4934(6) 2_655 ?
Si1 C7 1.699(15) . ?
Si1 C6' 1.768(13) . ?
Si1 C2 1.892(7) . ?
Si1 C6 2.075(12) . ?
Si1 C7' 2.094(13) . ?
Si1 Si1 2.309(3) 2 ?
N1 C1 1.340(7) . ?
N1 C5 1.343(9) . ?
C1 C2 1.378(8) . ?
C1 H1A 0.9500 . ?
C2 C3 1.394(11) . ?
C3 C4 1.379(12) . ?
C3 H3A 0.9500 . ?
C4 C5 1.388(13) . ?
C4 H4A 0.9500 . ?
C5 H5A 0.9500 . ?
C6 H6A 0.9800 . ?
C6 H6B 0.9800 . ?
C6 H6C 0.9800 . ?
C7 H7A 0.9800 . ?
C7 H7B 0.9800 . ?
C7 H7C 0.9800 . ?
C6' H6'A 0.9800 . ?
C6' H6'B 0.9800 . ?
C6' H6'C 0.9800 . ?
C7' H7'A 0.9800 . ?
C7' H7'B 0.9800 . ?
C7' H7'C 0.9800 . ?

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 90.0(3) 2_655 . ?
N1 Hg1 Br1 112.90(12) 2_655 . ?
N1 Hg1 Br1 100.41(12) . . ?
N1 Hg1 Br1 100.41(12) 2_655 2_655 ?
N1 Hg1 Br1 112.91(12) . 2_655 ?
Br1 Hg1 Br1 132.47(4) . 2_655 ?
C7 Si1 C2 108.2(6) . . ?
C6' Si1 C2 119.2(6) . . ?
C7 Si1 C6 109.3(7) . . ?
C2 Si1 C6 100.0(5) . . ?
C6' Si1 C7' 105.9(6) . . ?
C2 Si1 C7' 104.7(4) . . ?
C7 Si1 Si1 129.3(6) . 2 ?
C6' Si1 Si1 116.5(5) . 2 ?
C2 Si1 Si1 108.4(2) . 2 ?
C6 Si1 Si1 97.6(4) . 2 ?
C7' Si1 Si1 99.5(3) . 2 ?
C1 N1 C5 119.0(6) . . ?
C1 N1 Hg1 119.0(4) . . ?
C5 N1 Hg1 122.0(5) . . ?
N1 C1 C2 124.0(6) . . ?
N1 C1 H1A 118.0 . . ?
C2 C1 H1A 118.0 . . ?
C1 C2 C3 116.3(7) . . ?
C1 C2 Si1 120.1(5) . . ?
C3 C2 Si1 123.6(5) . . ?
C4 C3 C2 120.8(7) . . ?
C4 C3 H3A 119.6 . . ?
C2 C3 H3A 119.6 . . ?
C3 C4 C5 118.9(7) . . ?
C3 C4 H4A 120.6 . . ?
C5 C4 H4A 120.6 . . ?
N1 C5 C4 121.1(7) . . ?
N1 C5 H5A 119.4 . . ?
C4 C5 H5A 119.4 . . ?
Si1 C6 H6A 109.5 . . ?
Si1 C6 H6B 109.5 . . ?
H6A C6 H6B 109.5 . . ?
Si1 C6 H6C 109.5 . . ?
H6A C6 H6C 109.5 . . ?
H6B C6 H6C 109.5 . . ?
Si1 C7 H7A 109.5 . . ?
Si1 C7 H7B 109.5 . . ?
H7A C7 H7B 109.5 . . ?
Si1 C7 H7C 109.5 . . ?
H7A C7 H7C 109.5 . . ?
H7B C7 H7C 109.5 . . ?
Si1 C6' H6'A 109.5 . . ?
Si1 C6' H6'B 109.5 . . ?
H6'A C6' H6'B 109.5 . . ?
Si1 C6' H6'C 109.5 . . ?
H6'A C6' H6'C 109.5 . . ?
H6'B C6' H6'C 109.5 . . ?
Si1 C7' H7'A 109.5 . . ?
Si1 C7' H7'B 109.5 . . ?
H7'A C7' H7'B 109.5 . . ?
Si1 C7' H7'C 109.5 . . ?
H7'A C7' H7'C 109.5 . . ?
H7'B C7' H7'C 109.5 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C5 N1 C1 C2 -0.1(9) . . . . ?
Hg1 N1 C1 C2 177.9(4) . . . . ?
N1 C1 C2 C3 0.4(9) . . . . ?
N1 C1 C2 Si1 -179.8(4) . . . . ?
C7 Si1 C2 C1 -83.1(7) . . . . ?
C6' Si1 C2 C1 -162.4(6) . . . . ?
C6 Si1 C2 C1 162.7(6) . . . . ?
C7' Si1 C2 C1 -44.3(6) . . . . ?
Si1 Si1 C2 C1 61.2(5) 2 . . . ?
C7 Si1 C2 C3 96.7(8) . . . . ?
C6' Si1 C2 C3 17.3(8) . . . . ?
C6 Si1 C2 C3 -17.5(7) . . . . ?
C7' Si1 C2 C3 135.5(6) . . . . ?
Si1 Si1 C2 C3 -119.1(5) 2 . . . ?
C1 C2 C3 C4 -0.7(10) . . . . ?
Si1 C2 C3 C4 179.5(6) . . . . ?
C2 C3 C4 C5 0.7(12) . . . . ?
C1 N1 C5 C4 0.0(11) . . . . ?
Hg1 N1 C5 C4 -177.9(6) . . . . ?
C3 C4 C5 N1 -0.3(12) . . . . ?

_refine_diff_density_max         2.555
_refine_diff_density_min         -3.621
_refine_diff_density_rms         0.271

_vrf_PLAT972_nth                 
;
PROBLEM: Check Calcd Residual Density  0.91A From     Hg1      -3.79 eA-3  
RESPONSE: As the large negative (-3.79 eA-3) difference Fourier peak is
located at short distance from Hg1 (0.91 A), the peak is a ghost of the 
heavy Hg atom.
;

####################################################################### 
# 
# 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_002-Br-hv
_database_code_depnum_ccdc_archive 'CCDC 1485719'
_audit_update_record             
;
2016-06-15 deposited with the CCDC.
2016-08-12 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C14 H22 Br5 Cl Hg2 N2 Si2'
_chemical_formula_weight         1110.69

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Br Br -0.2901 2.4595 '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'
Hg Hg -2.3894 9.2266 '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'
Si Si 0.0817 0.0704 '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/n'
_space_group_name_Hall           '-P 2yn'

_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+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, -y-1/2, z-1/2'

_cell_length_a                   12.8706(7)
_cell_length_b                   8.2506(5)
_cell_length_c                   13.8348(10)
_cell_angle_alpha                90
_cell_angle_beta                 113.876(5)
_cell_angle_gamma                90
_cell_volume                     1343.40(15)
_cell_formula_units_Z            2
_cell_measurement_temperature    173(2)
_cell_measurement_reflns_used    418
_cell_measurement_theta_min      2.95
_cell_measurement_theta_max      14.41

_exptl_crystal_description       block
_exptl_crystal_colour            brown
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    2.746
_exptl_crystal_F_000             1000
_exptl_transmission_factor_min   0.051
_exptl_transmission_factor_max   0.084
_exptl_crystal_size_max          0.180
_exptl_crystal_size_mid          0.140
_exptl_crystal_size_min          0.130
_exptl_absorpt_coefficient_mu    19.043
_shelx_estimated_absorpt_T_min   0.131
_shelx_estimated_absorpt_T_max   0.191
_exptl_absorpt_correction_type   Multi-scan
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   SADABS
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      173(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruker Breeze CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            11348
_diffrn_reflns_av_unetI/netI     0.2640
_diffrn_reflns_av_R_equivalents  0.1378
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_theta_min         1.825
_diffrn_reflns_theta_max         25.998
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measured_fraction_theta_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_point_group_measured_fraction_full 1.000
_reflns_number_total             2630
_reflns_number_gt                982
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_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       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0471P)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_number_reflns         2630
_refine_ls_number_parameters     118
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1226
_refine_ls_R_factor_gt           0.0594
_refine_ls_wR_factor_ref         0.1436
_refine_ls_wR_factor_gt          0.1345
_refine_ls_goodness_of_fit_ref   0.693
_refine_ls_restrained_S_all      0.693
_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
Hg1 Hg 0.55788(8) 0.41623(10) 0.14312(7) 0.0522(3) Uani 1 1 d . . . . .
Br1 Br 0.4608(2) 0.5211(3) 0.25487(19) 0.0598(7) Uani 1 1 d . . . . .
Br2 Br 0.7019(2) 0.2026(3) 0.15274(19) 0.0652(8) Uani 1 1 d . . . . .
X3 Br 0.3754(2) 0.3410(3) -0.0468(2) 0.0312(7) Uani 0.5 1 d . . P . .
X3' Cl 0.3754(2) 0.3410(3) -0.0468(2) 0.0312(7) Uani 0.5 1 d . . P . .
Si1 Si 0.0098(5) 0.6191(6) 0.0484(5) 0.0420(15) Uani 1 1 d . . . . .
N1 N -0.0518(15) 0.4086(18) 0.2881(14) 0.049(5) Uani 1 1 d . . . . .
H1B H -0.1080 0.3519 0.2918 0.059 Uiso 1 1 calc R U . . .
C1 C -0.0662(16) 0.470(2) 0.1933(16) 0.040(5) Uani 1 1 d . . . . .
H1A H -0.1363 0.4571 0.1338 0.048 Uiso 1 1 calc R U . . .
C2 C 0.0228(15) 0.553(2) 0.1843(14) 0.029(5) Uani 1 1 d . . . . .
C3 C 0.1183(15) 0.572(2) 0.2728(16) 0.046(6) Uani 1 1 d . . . . .
H3A H 0.1808 0.6278 0.2685 0.055 Uiso 1 1 calc R U . . .
C4 C 0.1283(19) 0.512(2) 0.3713(17) 0.046(6) Uani 1 1 d . . . . .
H4A H 0.1953 0.5312 0.4331 0.055 Uiso 1 1 calc R U . . .
C5 C 0.0411(17) 0.428(2) 0.3764(16) 0.042(5) Uani 1 1 d . . . . .
H5A H 0.0459 0.3826 0.4413 0.050 Uiso 1 1 calc R U . . .
C6 C -0.1152(16) 0.757(3) -0.0065(18) 0.072(8) Uani 1 1 d . . . . .
H6A H -0.1844 0.6969 -0.0160 0.087 Uiso 1 1 calc R U . . .
H6B H -0.1054 0.8472 0.0425 0.087 Uiso 1 1 calc R U . . .
H6C H -0.1217 0.7994 -0.0749 0.087 Uiso 1 1 calc R U . . .
C7 C 0.1427(15) 0.732(2) 0.0670(17) 0.051(6) Uani 1 1 d . . . . .
H7A H 0.2080 0.6583 0.0958 0.062 Uiso 1 1 calc R U . . .
H7B H 0.1367 0.7741 -0.0013 0.062 Uiso 1 1 calc R U . . .
H7C H 0.1531 0.8219 0.1161 0.062 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 Br1 2.502(2) . ?
Hg1 Br2 2.522(3) . ?
Hg1 X3' 2.730(3) 3_665 ?
Hg1 X3 2.730(3) 3_665 ?
Hg1 X3 2.795(3) . ?
X3 Hg1 2.730(3) 3_665 ?
Si1 C6 1.864(18) . ?
Si1 C7 1.871(17) . ?
Si1 C2 1.901(18) . ?
Si1 Si1 2.332(11) 3_565 ?
N1 C5 1.33(2) . ?
N1 C1 1.35(2) . ?
N1 H1B 0.8800 . ?
C1 C2 1.38(2) . ?
C1 H1A 0.9500 . ?
C2 C3 1.35(2) . ?
C3 C4 1.40(2) . ?
C3 H3A 0.9500 . ?
C4 C5 1.35(3) . ?
C4 H4A 0.9500 . ?
C5 H5A 0.9500 . ?
C6 H6A 0.9800 . ?
C6 H6B 0.9800 . ?
C6 H6C 0.9800 . ?
C7 H7A 0.9800 . ?
C7 H7B 0.9800 . ?
C7 H7C 0.9800 . ?

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
Br1 Hg1 Br2 138.50(9) . . ?
Br1 Hg1 X3' 112.46(8) . 3_665 ?
Br2 Hg1 X3' 99.73(8) . 3_665 ?
Br1 Hg1 X3 112.46(8) . 3_665 ?
Br2 Hg1 X3 99.73(8) . 3_665 ?
X3' Hg1 X3 0.0 3_665 3_665 ?
Br1 Hg1 X3 102.60(8) . . ?
Br2 Hg1 X3 102.38(8) . . ?
X3' Hg1 X3 90.8 3_665 . ?
X3 Hg1 X3 90.85(8) 3_665 . ?
Hg1 X3 Hg1 89.15(8) 3_665 . ?
C6 Si1 C7 110.1(9) . . ?
C6 Si1 C2 107.1(9) . . ?
C7 Si1 C2 107.3(9) . . ?
C6 Si1 Si1 113.9(8) . 3_565 ?
C7 Si1 Si1 112.2(7) . 3_565 ?
C2 Si1 Si1 105.7(6) . 3_565 ?
C5 N1 C1 124.7(18) . . ?
C5 N1 H1B 117.7 . . ?
C1 N1 H1B 117.7 . . ?
N1 C1 C2 118.7(18) . . ?
N1 C1 H1A 120.6 . . ?
C2 C1 H1A 120.6 . . ?
C3 C2 C1 117.4(18) . . ?
C3 C2 Si1 123.2(15) . . ?
C1 C2 Si1 119.2(14) . . ?
C2 C3 C4 122.1(19) . . ?
C2 C3 H3A 118.9 . . ?
C4 C3 H3A 118.9 . . ?
C5 C4 C3 119(2) . . ?
C5 C4 H4A 120.6 . . ?
C3 C4 H4A 120.6 . . ?
N1 C5 C4 118(2) . . ?
N1 C5 H5A 120.9 . . ?
C4 C5 H5A 120.9 . . ?
Si1 C6 H6A 109.5 . . ?
Si1 C6 H6B 109.5 . . ?
H6A C6 H6B 109.5 . . ?
Si1 C6 H6C 109.5 . . ?
H6A C6 H6C 109.5 . . ?
H6B C6 H6C 109.5 . . ?
Si1 C7 H7A 109.5 . . ?
Si1 C7 H7B 109.5 . . ?
H7A C7 H7B 109.5 . . ?
Si1 C7 H7C 109.5 . . ?
H7A C7 H7C 109.5 . . ?
H7B C7 H7C 109.5 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C5 N1 C1 C2 3(3) . . . . ?
N1 C1 C2 C3 -2(3) . . . . ?
N1 C1 C2 Si1 173.1(13) . . . . ?
C1 C2 C3 C4 0(3) . . . . ?
Si1 C2 C3 C4 -175.7(14) . . . . ?
C2 C3 C4 C5 3(3) . . . . ?
C1 N1 C5 C4 -1(3) . . . . ?
C3 C4 C5 N1 -2(3) . . . . ?

_refine_diff_density_max         2.070
_refine_diff_density_min         -1.817
_refine_diff_density_rms         0.308

####################################################################### 
# 
# 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_003-I
_database_code_depnum_ccdc_archive 'CCDC 1485720'
_audit_update_record             
;
2016-06-15 deposited with the CCDC.
2016-08-12 downloaded from the CCDC.
;
# start Validation Reply Form
_vrf_PLAT972_003-I               
;
PROBLEM: Check Calcd Residual Density  0.06A From      I1      -4.30 eA-3
RESPONSE: As the large negative (-4.30 eA-3) difference Fourier peak is located at short distance from Hg1 (0.06 A), the peak is a ghost of the heavy Hg atom.
;
_vrf_PLAT972_003-I_2             
;
PROBLEM: Check Calcd Residual Density  1.05A From     Hg1      -3.65 eA-3
RESPONSE: As the large negative (-3.65 eA-3) difference Fourier peak is located at short distance from Hg1 (1.05 A), the peak is a ghost of the heavy Hg atom.
;
_vrf_PLAT974_003-I               
;
PROBLEM: Check Calcd Negative Residual Density on     Hg1      -4.81 eA-3
RESPONSE: As the large negative (-4.81 eA-3) difference Fourier peak is located at short distance from Hg1, the peak is a ghost of the heavy Hg atom.
;
# Added during the CSD deposition process: Wednesday 15 June 2016 08:59 AM
# end Validation Reply Form


_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C14 H20 Hg I2 N2 Si2'
_chemical_formula_weight         726.89

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'
Si Si 0.0817 0.0704 '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           15
_space_group_name_H-M_alt        'C 2/c'
_space_group_name_Hall           '-C 2yc'

_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'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y, z-1/2'
'-x+1/2, -y+1/2, -z'
'x+1/2, -y+1/2, z-1/2'

_cell_length_a                   9.5172(4)
_cell_length_b                   13.6206(4)
_cell_length_c                   16.3559(5)
_cell_angle_alpha                90
_cell_angle_beta                 98.700(2)
_cell_angle_gamma                90
_cell_volume                     2095.82(13)
_cell_formula_units_Z            4
_cell_measurement_temperature    173(2)
_cell_measurement_reflns_used    8836
_cell_measurement_theta_min      2.52
_cell_measurement_theta_max      28.49

_exptl_crystal_description       block
_exptl_crystal_colour            colorless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    2.304
_exptl_crystal_F_000             1328
_exptl_transmission_factor_min   0.071
_exptl_transmission_factor_max   0.154
_exptl_crystal_size_max          0.300
_exptl_crystal_size_mid          0.230
_exptl_crystal_size_min          0.180
_exptl_absorpt_coefficient_mu    10.400
_shelx_estimated_absorpt_T_min   0.146
_shelx_estimated_absorpt_T_max   0.256
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   SADABS
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      173(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruker Breeze Bruker'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            16984
_diffrn_reflns_av_unetI/netI     0.0319
_diffrn_reflns_av_R_equivalents  0.0639
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_theta_min         2.520
_diffrn_reflns_theta_max         26.490
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measured_fraction_theta_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 1.000
_diffrn_reflns_point_group_measured_fraction_full 1.000
_reflns_number_total             2177
_reflns_number_gt                2105
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_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       'Bruker APEX2'
_computing_cell_refinement       'Bruker APEX2'
_computing_data_reduction        'Bruker APEX2'
_computing_structure_solution    'SHELXS-97 (Sheldrick 2008)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0850P)²+9.5436P] 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         2177
_refine_ls_number_parameters     96
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0431
_refine_ls_R_factor_gt           0.0423
_refine_ls_wR_factor_ref         0.1141
_refine_ls_wR_factor_gt          0.1131
_refine_ls_goodness_of_fit_ref   1.046
_refine_ls_restrained_S_all      1.046
_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
Hg1 Hg 0.0000 0.18820(2) 0.2500 0.02172(15) Uani 1 2 d S T P . .
I1 I -0.25345(5) 0.26246(4) 0.26512(3) 0.03440(18) Uani 1 1 d . . . . .
Si1 Si 0.41388(17) 0.03822(12) 0.53200(9) 0.0178(3) Uani 1 1 d . . . . .
C1 C -0.0077(6) -0.0192(5) 0.3575(4) 0.0219(12) Uani 1 1 d . . . . .
H1A H -0.0926 -0.0299 0.3199 0.026 Uiso 1 1 calc R U . . .
C4 C 0.2386(6) 0.0105(4) 0.4662(3) 0.0164(11) Uani 1 1 d . . . . .
N1 N 0.0673(5) 0.0619(4) 0.3504(3) 0.0178(9) Uani 1 1 d . . . . .
C5 C 0.1870(6) 0.0747(4) 0.4030(4) 0.0195(11) Uani 1 1 d . . . . .
H5A H 0.2411 0.1321 0.3968 0.023 Uiso 1 1 calc R U . . .
C2 C 0.0336(7) -0.0875(5) 0.4172(4) 0.0284(14) Uani 1 1 d . . . . .
H2A H -0.0223 -0.1445 0.4213 0.034 Uiso 1 1 calc R U . . .
C3 C 0.1582(7) -0.0729(5) 0.4719(4) 0.0262(13) Uani 1 1 d . . . . .
H3A H 0.1883 -0.1204 0.5134 0.031 Uiso 1 1 calc R U . . .
C7 C 0.4425(10) 0.1735(5) 0.5322(6) 0.046(2) Uani 1 1 d . . . . .
H7A H 0.4392 0.1967 0.4752 0.055 Uiso 1 1 calc R U . . .
H7B H 0.3679 0.2061 0.5574 0.055 Uiso 1 1 calc R U . . .
H7C H 0.5356 0.1889 0.5640 0.055 Uiso 1 1 calc R U . . .
C6 C 0.4195(10) -0.0086(8) 0.6391(4) 0.048(2) Uani 1 1 d . . . . .
H6A H 0.4042 -0.0798 0.6376 0.057 Uiso 1 1 calc R U . . .
H6B H 0.5124 0.0061 0.6714 0.057 Uiso 1 1 calc R U . . .
H6C H 0.3447 0.0232 0.6648 0.057 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 2.397(5) . ?
Hg1 N1 2.397(5) 2 ?
Hg1 I1 2.6614(5) . ?
Hg1 I1 2.6614(5) 2 ?
Si1 C6 1.857(7) . ?
Si1 C7 1.862(8) . ?
Si1 C4 1.882(6) . ?
Si1 Si1 2.321(3) 5_656 ?
C1 N1 1.330(8) . ?
C1 C2 1.363(9) . ?
C1 H1A 0.9500 . ?
C4 C3 1.380(9) . ?
C4 C5 1.385(8) . ?
N1 C5 1.332(8) . ?
C5 H5A 0.9500 . ?
C2 C3 1.387(10) . ?
C2 H2A 0.9500 . ?
C3 H3A 0.9500 . ?
C7 H7A 0.9800 . ?
C7 H7B 0.9800 . ?
C7 H7C 0.9800 . ?
C6 H6A 0.9800 . ?
C6 H6B 0.9800 . ?
C6 H6C 0.9800 . ?

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 88.3(2) . 2 ?
N1 Hg1 I1 111.17(12) . . ?
N1 Hg1 I1 100.62(12) 2 . ?
N1 Hg1 I1 100.63(12) . 2 ?
N1 Hg1 I1 111.17(12) 2 2 ?
I1 Hg1 I1 135.32(3) . 2 ?
C6 Si1 C7 110.8(5) . . ?
C6 Si1 C4 111.5(3) . . ?
C7 Si1 C4 108.4(3) . . ?
C6 Si1 Si1 110.5(3) . 5_656 ?
C7 Si1 Si1 109.4(4) . 5_656 ?
C4 Si1 Si1 106.12(19) . 5_656 ?
N1 C1 C2 121.9(6) . . ?
N1 C1 H1A 119.0 . . ?
C2 C1 H1A 119.0 . . ?
C3 C4 C5 115.6(5) . . ?
C3 C4 Si1 125.4(5) . . ?
C5 C4 Si1 118.9(4) . . ?
C1 N1 C5 118.0(5) . . ?
C1 N1 Hg1 124.4(4) . . ?
C5 N1 Hg1 117.6(4) . . ?
N1 C5 C4 124.9(6) . . ?
N1 C5 H5A 117.6 . . ?
C4 C5 H5A 117.6 . . ?
C1 C2 C3 119.4(6) . . ?
C1 C2 H2A 120.3 . . ?
C3 C2 H2A 120.3 . . ?
C4 C3 C2 120.2(6) . . ?
C4 C3 H3A 119.9 . . ?
C2 C3 H3A 119.9 . . ?
Si1 C7 H7A 109.5 . . ?
Si1 C7 H7B 109.5 . . ?
H7A C7 H7B 109.5 . . ?
Si1 C7 H7C 109.5 . . ?
H7A C7 H7C 109.5 . . ?
H7B C7 H7C 109.5 . . ?
Si1 C6 H6A 109.5 . . ?
Si1 C6 H6B 109.5 . . ?
H6A C6 H6B 109.5 . . ?
Si1 C6 H6C 109.5 . . ?
H6A C6 H6C 109.5 . . ?
H6B C6 H6C 109.5 . . ?

_refine_diff_density_max         0.857
_refine_diff_density_min         -4.890
_refine_diff_density_rms         0.480

####################################################################### 
# 
# 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_004-I-hv
_database_code_depnum_ccdc_archive 'CCDC 1485721'
_audit_update_record             
;
2016-06-15 deposited with the CCDC.
2016-08-12 downloaded from the CCDC.
;
# start Validation Reply Form
_vrf_PLAT971_004-I-hv            
;
PROBLEM: Check Calcd Residual Density  0.76A From     Hg1       3.75 eA-3
RESPONSE: As the large (3.75 eA-3) difference Fourier peak is located at short distance from Hg1 (3.75 A), the peak is a ghost of the heavy Hg atom.
;
# Added during the CSD deposition process: Wednesday 15 June 2016 08:59 AM
# end Validation Reply Form


_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C14 H22 Cl2 Hg2 I4 N2 Si2'
_chemical_formula_weight         1254.19

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'
Si Si 0.0817 0.0704 '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      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                   8.3261(2)
_cell_length_b                   22.1706(4)
_cell_length_c                   8.2547(2)
_cell_angle_alpha                90
_cell_angle_beta                 111.0420(10)
_cell_angle_gamma                90
_cell_volume                     1422.16(6)
_cell_formula_units_Z            2
_cell_measurement_temperature    194(2)
_cell_measurement_reflns_used    8371
_cell_measurement_theta_min      2.62
_cell_measurement_theta_max      28.24

_exptl_crystal_description       block
_exptl_crystal_colour            brown
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    2.929
_exptl_crystal_F_000             1108
_exptl_transmission_factor_min   0.001
_exptl_transmission_factor_max   0.003
_exptl_crystal_size_max          0.600
_exptl_crystal_size_mid          0.080
_exptl_crystal_size_min          0.040
_exptl_absorpt_coefficient_mu    15.400
_shelx_estimated_absorpt_T_min   0.039
_shelx_estimated_absorpt_T_max   0.578
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.039
_exptl_absorpt_correction_T_max  0.578
_exptl_absorpt_process_details   SADABS
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      194(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruker Breeze CCD'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            25016
_diffrn_reflns_av_unetI/netI     0.0249
_diffrn_reflns_av_R_equivalents  0.0357
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_k_min       -29
_diffrn_reflns_limit_k_max       29
_diffrn_reflns_limit_l_min       -10
_diffrn_reflns_limit_l_max       10
_diffrn_reflns_theta_min         1.837
_diffrn_reflns_theta_max         28.309
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measured_fraction_theta_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_point_group_measured_fraction_full 1.000
_reflns_number_total             3527
_reflns_number_gt                3118
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_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       'Bruker APEX2'
_computing_cell_refinement       'Bruker APEX2'
_computing_data_reduction        'Bruker APEX2'
_computing_structure_solution    'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0427P)²+11.6389P] 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         3527
_refine_ls_number_parameters     118
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0434
_refine_ls_R_factor_gt           0.0372
_refine_ls_wR_factor_ref         0.0988
_refine_ls_wR_factor_gt          0.0958
_refine_ls_goodness_of_fit_ref   1.046
_refine_ls_restrained_S_all      1.046
_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
Hg1 Hg 0.15814(4) 0.21153(2) 0.91066(5) 0.04479(11) Uani 1 1 d . . . . .
I1 I 0.23447(7) 0.09688(2) 0.89574(7) 0.04149(14) Uani 1 1 d . . . . .
I2 I -0.05338(7) 0.29345(2) 0.94983(7) 0.04253(14) Uani 1 1 d . . . . .
Cl1 Cl 0.3690(2) 0.27923(8) 0.8079(2) 0.0356(4) Uani 1 1 d . . . . .
Si1 Si -0.3603(2) 0.01919(9) 0.5348(2) 0.0275(4) Uani 1 1 d . . . . .
N1 N -0.4059(8) 0.1700(3) 0.8045(9) 0.0374(14) Uani 1 1 d . . . . .
H1B H -0.4671 0.2034 0.7775 0.045 Uiso 1 1 calc R U . . .
C1 C -0.4204(9) 0.1299(3) 0.6789(9) 0.0329(14) Uani 1 1 d . . . . .
H1A H -0.4946 0.1386 0.5637 0.039 Uiso 1 1 calc R U . . .
C2 C -0.3307(8) 0.0763(3) 0.7118(8) 0.0265(12) Uani 1 1 d . . . . .
C3 C -0.2208(9) 0.0673(3) 0.8854(9) 0.0328(14) Uani 1 1 d . . . . .
H3A H -0.1552 0.0312 0.9158 0.039 Uiso 1 1 calc R U . . .
C4 C -0.2060(10) 0.1105(4) 1.0146(10) 0.0404(17) Uani 1 1 d . . . . .
H4A H -0.1303 0.1043 1.1308 0.048 Uiso 1 1 calc R U . . .
C5 C -0.3022(10) 0.1614(4) 0.9694(11) 0.0410(17) Uani 1 1 d . . . . .
H5A H -0.2961 0.1910 1.0548 0.049 Uiso 1 1 calc R U . . .
C6 C -0.3387(11) 0.0590(4) 0.3453(10) 0.0428(18) Uani 1 1 d . . . . .
H6A H -0.4284 0.0899 0.3038 0.051 Uiso 1 1 calc R U . . .
H6B H -0.2252 0.0782 0.3802 0.051 Uiso 1 1 calc R U . . .
H6C H -0.3509 0.0300 0.2522 0.051 Uiso 1 1 calc R U . . .
C7 C -0.1913(10) -0.0406(4) 0.6199(11) 0.0426(18) Uani 1 1 d . . . . .
H7A H -0.2059 -0.0607 0.7193 0.051 Uiso 1 1 calc R U . . .
H7B H -0.2026 -0.0702 0.5284 0.051 Uiso 1 1 calc R U . . .
H7C H -0.0770 -0.0220 0.6564 0.051 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 I2 2.6295(6) . ?
Hg1 I1 2.6337(6) . ?
Hg1 Cl1 2.6687(18) . ?
Si1 C6 1.861(8) . ?
Si1 C7 1.876(8) . ?
Si1 C2 1.881(7) . ?
Si1 Si1 2.346(4) 3_456 ?
N1 C1 1.338(10) . ?
N1 C5 1.338(11) . ?
C1 C2 1.378(10) . ?
C2 C3 1.410(9) . ?
C3 C4 1.406(11) . ?
C4 C5 1.357(12) . ?

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
I2 Hg1 I1 148.86(2) . . ?
I2 Hg1 Cl1 101.34(4) . . ?
I1 Hg1 Cl1 109.31(4) . . ?
C6 Si1 C7 111.3(4) . . ?
C6 Si1 C2 108.0(3) . . ?
C7 Si1 C2 108.2(3) . . ?
C6 Si1 Si1 110.7(3) . 3_456 ?
C7 Si1 Si1 112.3(3) . 3_456 ?
C2 Si1 Si1 106.0(2) . 3_456 ?
C1 N1 C5 122.7(7) . . ?
N1 C1 C2 122.0(6) . . ?
C1 C2 C3 115.5(6) . . ?
C1 C2 Si1 121.1(5) . . ?
C3 C2 Si1 123.4(5) . . ?
C4 C3 C2 121.5(7) . . ?
C5 C4 C3 118.5(7) . . ?
N1 C5 C4 119.9(7) . . ?

_refine_diff_density_max         3.603
_refine_diff_density_min         -2.121
_refine_diff_density_rms         0.198

