# 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_shelxl
_database_code_depnum_ccdc_archive 'CCDC 1016899'
_audit_update_record             
;
2014-07-29 deposited with the CCDC.
2016-05-24 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C15 H10 Br1 Hg1 I2 N3 O1'
_chemical_formula_sum            'C15 H10 Br1 Hg1 I2 N3 O1'
_chemical_formula_weight         782.44

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Hg Hg -2.3894 9.2266 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
I I -0.4742 1.8119 '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'

_symmetry_cell_setting           Monoclinic
_symmetry_space_group_name_Hall  '-P 2yb'
_symmetry_space_group_name_H-M   'P 21/m'
_symmetry_Int_Tables_number      11

loop_
_symmetry_equiv_pos_site_id
_symmetry_equiv_pos_as_xyz
1 x,y,z
2 -x,1/2+y,-z
3 -x,-y,-z
4 x,1/2-y,z

_cell_length_a                   10.133(3)
_cell_length_b                   6.7797(17)
_cell_length_c                   13.077(3)
_cell_angle_alpha                90.00
_cell_angle_beta                 91.44(2)
_cell_angle_gamma                90.00
_cell_volume                     898.1(4)
_cell_formula_units_Z            2
_cell_measurement_temperature    298(2)
_cell_measurement_reflns_used    856
_cell_measurement_theta_min      2.01
_cell_measurement_theta_max      29.45

_exptl_crystal_description       Needle
_exptl_crystal_colour            Colorless
_exptl_crystal_size_max          0.50
_exptl_crystal_size_mid          0.05
_exptl_crystal_size_min          0.04
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    2.894
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             700
_exptl_absorpt_coefficient_mu    14.237
_exptl_absorpt_correction_type   numerical
_exptl_absorpt_correction_T_min  0.0562
_exptl_absorpt_correction_T_max  0.3473
_exptl_absorpt_process_details   'shape of crystal determined optically'

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      298(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'STOE IPDS II'
_diffrn_measurement_method       'rotation method'
_diffrn_detector_area_resol_mean '0.15 mm'
_diffrn_standards_number         0
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            5365
_diffrn_reflns_av_R_equivalents  0.1140
_diffrn_reflns_av_sigmaI/netI    0.0675
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_theta_min         2.01
_diffrn_reflns_theta_max         29.45
_reflns_number_total             2586
_reflns_number_gt                2066
_reflns_threshold_expression     >2sigma(I)

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

_refine_special_details          
; 
 Refinement of F² against ALL reflections.  The weighted R-factor wR and 
 goodness of fit S are based on F², conventional R-factors R are based 
 on F, with F set to zero for negative F². The threshold expression of 
 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is 
 not relevant to the choice of reflections for refinement.  R-factors based 
 on F² are statistically about twice as large as those based on F, and R- 
 factors based on ALL data will be even larger. 
;

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.1819P)²+3.2148P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     SHELXL
_refine_ls_number_reflns         2586
_refine_ls_number_parameters     140
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0903
_refine_ls_R_factor_gt           0.0718
_refine_ls_wR_factor_ref         0.1990
_refine_ls_wR_factor_gt          0.1856
_refine_ls_goodness_of_fit_ref   1.099
_refine_ls_restrained_S_all      1.099
_refine_ls_shift/su_max          0.004
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C 0.4429(19) 0.2500 0.271(2) 0.058(5) Uani 1 2 d S . .
H1 H 0.5232 0.2500 0.3067 0.069 Uiso 1 2 calc SR . .
C2 C 0.3245(19) 0.2500 0.3271(13) 0.045(4) Uani 1 2 d S . .
H2 H 0.3285 0.2500 0.3983 0.054 Uiso 1 2 calc SR . .
C3 C 0.2084(17) 0.2500 0.1751(13) 0.040(3) Uani 1 2 d S . .
H3 H 0.1288 0.2500 0.1380 0.048 Uiso 1 2 calc SR . .
C4 C 0.3280(15) 0.2500 0.1246(15) 0.041(3) Uani 1 2 d S . .
C5 C 0.3262(17) 0.2500 0.0071(16) 0.044(4) Uani 1 2 d S . .
C6 C 0.4951(15) 0.2500 -0.1279(13) 0.040(3) Uani 1 2 d S . .
C7 C 0.4088(17) 0.2500 -0.2081(15) 0.046(4) Uani 1 2 d S . .
H7 H 0.3184 0.2500 -0.1975 0.056 Uiso 1 2 calc SR . .
C8 C 0.4570(16) 0.2500 -0.3083(17) 0.051(4) Uani 1 2 d S . .
H8 H 0.3963 0.2500 -0.3628 0.062 Uiso 1 2 calc SR . .
C9 C 0.5906(18) 0.2500 -0.3295(16) 0.048(4) Uani 1 2 d S . .
C10 C 0.6817(15) 0.2500 -0.2438(14) 0.042(4) Uani 1 2 d S . .
C11 C 0.8197(18) 0.2500 -0.2601(19) 0.053(5) Uani 1 2 d S . .
H11 H 0.8523 0.2500 -0.3259 0.064 Uiso 1 2 calc SR . .
C12 C 0.9067(16) 0.2500 -0.1728(19) 0.052(5) Uani 1 2 d S . .
H12 H 0.9976 0.2500 -0.1811 0.062 Uiso 1 2 calc SR . .
C13 C 0.8590(19) 0.2500 -0.082(2) 0.057(5) Uani 1 2 d S . .
H13 H 0.9191 0.2500 -0.0266 0.069 Uiso 1 2 calc SR . .
C14 C 0.728(2) 0.2500 -0.0595(15) 0.048(4) Uani 1 2 d S . .
H14 H 0.7012 0.2500 0.0079 0.058 Uiso 1 2 calc SR . .
C15 C 0.6341(14) 0.2500 -0.1428(12) 0.034(3) Uani 1 2 d S . .
N1 N 0.4444(15) 0.2500 0.1732(13) 0.045(3) Uani 1 2 d S . .
N2 N 0.2092(14) 0.2500 0.2781(18) 0.059(5) Uani 1 2 d S . .
N3 N 0.4500(14) 0.2500 -0.0270(11) 0.042(3) Uani 1 2 d S . .
H3A H 0.5110 0.2500 0.0199 0.051 Uiso 1 2 calc SR . .
O1 O 0.2250(14) 0.2500 -0.0388(10) 0.060(4) Uani 1 2 d S . .
Hg1 Hg -0.00214(7) 0.2500 0.37806(6) 0.0506(4) Uani 1 2 d S . .
I1 I -0.17595(14) 0.2500 0.23085(12) 0.0651(5) Uani 1 2 d S . .
I2 I 0.10950(12) 0.2500 0.55962(10) 0.0525(4) Uani 1 2 d S . .
Br1 Br 0.6478(3) 0.2500 -0.46324(17) 0.0684(7) Uani 1 2 d S . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
C1 N1 1.27(3) . ?
C1 C2 1.43(3) . ?
C1 H1 0.9300 . ?
C2 N2 1.32(3) . ?
C2 H2 0.9300 . ?
C3 N2 1.35(3) . ?
C3 C4 1.40(2) . ?
C3 H3 0.9300 . ?
C4 N1 1.33(2) . ?
C4 C5 1.54(3) . ?
C5 O1 1.18(2) . ?
C5 N3 1.34(2) . ?
C6 C7 1.35(3) . ?
C6 N3 1.41(2) . ?
C6 C15 1.43(2) . ?
C7 C8 1.41(3) . ?
C7 H7 0.9300 . ?
C8 C9 1.39(2) . ?
C8 H8 0.9300 . ?
C9 C10 1.43(3) . ?
C9 Br1 1.86(2) . ?
C10 C15 1.42(2) . ?
C10 C11 1.42(2) . ?
C11 C12 1.43(3) . ?
C11 H11 0.9300 . ?
C12 C13 1.30(3) . ?
C12 H12 0.9300 . ?
C13 C14 1.36(3) . ?
C13 H13 0.9300 . ?
C14 C15 1.43(2) . ?
C14 H14 0.9300 . ?
N2 Hg1 2.537(15) . ?
N3 H3A 0.8600 . ?
Hg1 I1 2.5763(16) . ?
Hg1 I2 2.6042(15) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
N1 C1 C2 123.3(18) . . ?
N1 C1 H1 118.3 . . ?
C2 C1 H1 118.3 . . ?
N2 C2 C1 119.7(18) . . ?
N2 C2 H2 120.1 . . ?
C1 C2 H2 120.1 . . ?
N2 C3 C4 119.3(16) . . ?
N2 C3 H3 120.3 . . ?
C4 C3 H3 120.3 . . ?
N1 C4 C3 123.1(17) . . ?
N1 C4 C5 117.9(13) . . ?
C3 C4 C5 119.0(15) . . ?
O1 C5 N3 129.9(19) . . ?
O1 C5 C4 119.9(15) . . ?
N3 C5 C4 110.2(15) . . ?
C7 C6 N3 120.6(15) . . ?
C7 C6 C15 121.1(15) . . ?
N3 C6 C15 118.3(15) . . ?
C6 C7 C8 119.4(15) . . ?
C6 C7 H7 120.3 . . ?
C8 C7 H7 120.3 . . ?
C9 C8 C7 123.3(18) . . ?
C9 C8 H8 118.4 . . ?
C7 C8 H8 118.4 . . ?
C8 C9 C10 117.0(19) . . ?
C8 C9 Br1 121.2(16) . . ?
C10 C9 Br1 121.8(13) . . ?
C15 C10 C11 119.9(17) . . ?
C15 C10 C9 120.1(14) . . ?
C11 C10 C9 120.0(18) . . ?
C10 C11 C12 118(2) . . ?
C10 C11 H11 120.9 . . ?
C12 C11 H11 120.9 . . ?
C13 C12 C11 119.9(17) . . ?
C13 C12 H12 120.1 . . ?
C11 C12 H12 120.1 . . ?
C12 C13 C14 126(2) . . ?
C12 C13 H13 117.2 . . ?
C14 C13 H13 117.2 . . ?
C13 C14 C15 118.2(19) . . ?
C13 C14 H14 120.9 . . ?
C15 C14 H14 120.9 . . ?
C10 C15 C6 119.2(14) . . ?
C10 C15 C14 118.2(15) . . ?
C6 C15 C14 122.6(16) . . ?
C1 N1 C4 116.6(15) . . ?
C2 N2 C3 118.0(15) . . ?
C2 N2 Hg1 119.9(15) . . ?
C3 N2 Hg1 122.1(12) . . ?
C5 N3 C6 129.8(16) . . ?
C5 N3 H3A 115.1 . . ?
C6 N3 H3A 115.1 . . ?
N2 Hg1 I1 100.7(5) . . ?
N2 Hg1 I2 96.7(5) . . ?
I1 Hg1 I2 162.63(6) . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
N1 C1 C2 N2 0.000(3) . . . . ?
N2 C3 C4 N1 0.000(2) . . . . ?
N2 C3 C4 C5 180.000(2) . . . . ?
N1 C4 C5 O1 180.000(1) . . . . ?
C3 C4 C5 O1 0.000(1) . . . . ?
N1 C4 C5 N3 0.000(1) . . . . ?
C3 C4 C5 N3 180.0 . . . . ?
N3 C6 C7 C8 180.000(2) . . . . ?
C15 C6 C7 C8 0.000(2) . . . . ?
C6 C7 C8 C9 0.000(3) . . . . ?
C7 C8 C9 C10 0.000(3) . . . . ?
C7 C8 C9 Br1 180.000(1) . . . . ?
C8 C9 C10 C15 0.000(3) . . . . ?
Br1 C9 C10 C15 180.000(2) . . . . ?
C8 C9 C10 C11 180.000(2) . . . . ?
Br1 C9 C10 C11 0.000(3) . . . . ?
C15 C10 C11 C12 0.000(2) . . . . ?
C9 C10 C11 C12 180.000(2) . . . . ?
C10 C11 C12 C13 0.000(2) . . . . ?
C11 C12 C13 C14 0.000(1) . . . . ?
C12 C13 C14 C15 0.000(1) . . . . ?
C11 C10 C15 C6 180.000(1) . . . . ?
C9 C10 C15 C6 0.000(2) . . . . ?
C11 C10 C15 C14 0.000(2) . . . . ?
C9 C10 C15 C14 180.000(2) . . . . ?
C7 C6 C15 C10 0.000(2) . . . . ?
N3 C6 C15 C10 180.000(1) . . . . ?
C7 C6 C15 C14 180.000(1) . . . . ?
N3 C6 C15 C14 0.000(1) . . . . ?
C13 C14 C15 C10 0.000(1) . . . . ?
C13 C14 C15 C6 180.0 . . . . ?
C2 C1 N1 C4 0.000(2) . . . . ?
C3 C4 N1 C1 0.000(2) . . . . ?
C5 C4 N1 C1 180.000(2) . . . . ?
C1 C2 N2 C3 0.000(2) . . . . ?
C1 C2 N2 Hg1 180.000(1) . . . . ?
C4 C3 N2 C2 0.000(2) . . . . ?
C4 C3 N2 Hg1 180.0 . . . . ?
O1 C5 N3 C6 0.0 . . . . ?
C4 C5 N3 C6 180.0 . . . . ?
C7 C6 N3 C5 0.000(1) . . . . ?
C15 C6 N3 C5 180.0 . . . . ?
C2 N2 Hg1 I1 180.000(2) . . . . ?
C3 N2 Hg1 I1 0.000(1) . . . . ?
C2 N2 Hg1 I2 0.000(2) . . . . ?
C3 N2 Hg1 I2 180.000(1) . . . . ?

_diffrn_measured_fraction_theta_max 0.985
_diffrn_reflns_theta_full        29.45
_diffrn_measured_fraction_theta_full 0.985
_refine_diff_density_max         1.220
_refine_diff_density_min         -1.210
_refine_diff_density_rms         0.502


loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
_geom_hbond_publ_flag
#
#D   H   A   D - H  H...A   D...A    D - H...A  symm(A)
#
N3 H3A N1 0.8600 2.1300 2.62(2) 116.00 . yes
C7 H7 O1 0.9300 2.3000 2.93(2) 124.00 . yes
C8 H8 I2 0.9300 3.0500 3.883(18) 149.00 1_554 yes
C8 H8 I2 0.9300 3.0500 3.883(18) 149.00 4_554 yes
C11 H11 I2 0.9300 3.0400 3.81(2) 142.00 1_654 yes
C11 H11 Br1 0.9300 2.7100 3.14(2) 109.00 . yes
C11 H11 I2 0.9300 3.0400 3.81(2) 142.00 4_654 yes
####################################################################### 
# 
# 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_shelxl
_database_code_depnum_ccdc_archive 'CCDC 1016900'
_audit_update_record             
;
2014-07-29 deposited with the CCDC.
2016-05-24 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C15 H10 Br3 Hg1 N3 O1'
_chemical_formula_sum            'C15 H10 Br3 Hg1 N3 O1'
_chemical_formula_weight         688.55

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'
Hg Hg -2.3894 9.2266 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Br Br -0.2901 2.4595 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_symmetry_cell_setting           Monoclinic
_symmetry_space_group_name_Hall  '-P 2yb'
_symmetry_space_group_name_H-M   'P 21/m'
_symmetry_Int_Tables_number      11

loop_
_symmetry_equiv_pos_site_id
_symmetry_equiv_pos_as_xyz
1 x,y,z
2 -x,1/2+y,-z
3 -x,-y,-z
4 x,1/2-y,z

_cell_length_a                   9.8327(14)
_cell_length_b                   6.6591(13)
_cell_length_c                   12.8974(17)
_cell_angle_alpha                90.00
_cell_angle_beta                 91.698(11)
_cell_angle_gamma                90.00
_cell_volume                     844.1(2)
_cell_formula_units_Z            2
_cell_measurement_temperature    298(2)
_cell_measurement_reflns_used    856
_cell_measurement_theta_min      2.07
_cell_measurement_theta_max      29.45

_exptl_crystal_description       Needle
_exptl_crystal_colour            Colorless
_exptl_crystal_size_max          0.12
_exptl_crystal_size_mid          0.03
_exptl_crystal_size_min          0.02
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    2.709
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             628
_exptl_absorpt_correction_type   numerical
_exptl_absorpt_correction_T_min  0.2086
_exptl_absorpt_correction_T_max  0.5134
_exptl_absorpt_process_details   'shape of crystal determined optically'

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      298(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'STOE IPDS II'
_diffrn_measurement_method       'rotation method'
_diffrn_detector_area_resol_mean '0.15 mm'
_diffrn_standards_number         0
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            7757
_diffrn_reflns_av_R_equivalents  0.1100
_diffrn_reflns_av_sigmaI/netI    0.1337
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_theta_min         2.07
_diffrn_reflns_theta_max         29.25
_reflns_number_total             2373
_reflns_number_gt                1568
_reflns_threshold_expression     >2sigma(I)

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

_refine_special_details          
; 
 Refinement of F² against ALL reflections.  The weighted R-factor wR and 
 goodness of fit S are based on F², conventional R-factors R are based 
 on F, with F set to zero for negative F². The threshold expression of 
 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is 
 not relevant to the choice of reflections for refinement.  R-factors based 
 on F² are statistically about twice as large as those based on F, and R- 
 factors based on ALL data will be even larger. 
;

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.1168P)²+2.0035P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         2373
_refine_ls_number_parameters     139
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0952
_refine_ls_R_factor_gt           0.0906
_refine_ls_wR_factor_ref         0.1920
_refine_ls_wR_factor_gt          0.1710
_refine_ls_goodness_of_fit_ref   1.149
_refine_ls_restrained_S_all      1.149
_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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
Hg1 Hg 0.48429(8) 0.7500 0.38609(8) 0.0563(4) Uani 1 2 d S . .
Br1 Br 0.3176(3) 0.7500 0.2449(3) 0.0769(9) Uani 1 2 d S . .
Br2 Br 0.5979(2) 0.7500 0.5578(2) 0.0690(8) Uani 1 2 d S . .
Br3 Br 1.1467(3) 0.7500 -0.4654(2) 0.0684(8) Uani 1 2 d S . .
O1 O 0.7109(17) 0.7500 -0.0411(13) 0.070(5) Uani 1 2 d S . .
N1 N 0.9380(16) 0.7500 0.1763(16) 0.051(4) Uani 1 2 d S . .
N2 N 0.698(2) 0.7500 0.2867(14) 0.051(4) Uani 1 2 d S . .
N3 N 0.9425(15) 0.7500 -0.0256(16) 0.050(4) Uani 1 2 d S . .
H3A H 1.0058 0.7500 0.0218 0.060 Uiso 1 2 calc SR . .
C1 C 0.9411(18) 0.7500 0.278(2) 0.051(5) Uani 1 2 d S . .
H1 H 1.0250 0.7500 0.3136 0.061 Uiso 1 2 calc SR . .
C2 C 0.819(2) 0.7500 0.337(2) 0.052(5) Uani 1 2 d S . .
H2 H 0.8246 0.7500 0.4087 0.063 Uiso 1 2 calc SR . .
C3 C 0.696(2) 0.7500 0.1836(18) 0.046(5) Uani 1 2 d S . .
H3 H 0.6116 0.7500 0.1483 0.055 Uiso 1 2 calc SR . .
C4 C 0.815(2) 0.7500 0.1249(19) 0.050(5) Uani 1 2 d S . .
C5 C 0.816(2) 0.7500 0.009(2) 0.049(5) Uani 1 2 d S . .
C6 C 0.9867(18) 0.7500 -0.1262(16) 0.040(4) Uani 1 2 d S . .
C7 C 0.900(2) 0.7500 -0.2117(17) 0.051(6) Uani 1 2 d S . .
H7 H 0.8066 0.7500 -0.2021 0.062 Uiso 1 2 calc SR . .
C8 C 0.949(2) 0.7500 -0.314(2) 0.055(6) Uani 1 2 d S . .
H8 H 0.8881 0.7500 -0.3712 0.067 Uiso 1 2 calc SR . .
C9 C 1.087(2) 0.7500 -0.3286(19) 0.049(5) Uani 1 2 d S . .
C10 C 1.1794(19) 0.7500 -0.2431(17) 0.045(5) Uani 1 2 d S . .
C11 C 1.324(2) 0.7500 -0.259(2) 0.055(6) Uani 1 2 d S . .
H11 H 1.3581 0.7500 -0.3253 0.066 Uiso 1 2 calc SR . .
C12 C 1.412(2) 0.7500 -0.173(2) 0.057(6) Uani 1 2 d S . .
H12 H 1.5051 0.7500 -0.1827 0.069 Uiso 1 2 calc SR . .
C13 C 1.367(2) 0.7500 -0.074(2) 0.060(7) Uani 1 2 d S . .
H13 H 1.4278 0.7500 -0.0174 0.072 Uiso 1 2 calc SR . .
C14 C 1.2271(19) 0.7500 -0.0585(18) 0.044(5) Uani 1 2 d S . .
H14 H 1.1971 0.7500 0.0092 0.052 Uiso 1 2 calc SR . .
C15 C 1.130(2) 0.7500 -0.1395(18) 0.044(5) Uani 1 2 d S . .


_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 2.413(3) . ?
Hg1 Br2 2.450(3) . ?
Hg1 N2 2.49(2) . ?
Br3 C9 1.88(3) . ?
O1 C5 1.20(3) . ?
N1 C1 1.31(3) . ?
N1 C4 1.36(3) . ?
N2 C3 1.33(3) . ?
N2 C2 1.34(3) . ?
N3 C5 1.34(3) . ?
N3 C6 1.38(3) . ?
N3 H3A 0.8600 . ?
C1 C2 1.43(3) . ?
C1 H1 0.9300 . ?
C2 H2 0.9300 . ?
C3 C4 1.41(3) . ?
C3 H3 0.9300 . ?
C4 C5 1.49(4) . ?
C6 C7 1.37(3) . ?
C6 C15 1.43(3) . ?
C7 C8 1.42(4) . ?
C7 H7 0.9300 . ?
C8 C9 1.38(3) . ?
C8 H8 0.9300 . ?
C9 C10 1.41(3) . ?
C10 C15 1.43(3) . ?
C10 C11 1.44(3) . ?
C11 C12 1.38(4) . ?
C11 H11 0.9300 . ?
C12 C13 1.36(4) . ?
C12 H12 0.9300 . ?
C13 C14 1.39(3) . ?
C13 H13 0.9300 . ?
C14 C15 1.39(3) . ?
C14 H14 0.9300 . ?

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 164.36(11) . . ?
Br1 Hg1 N2 100.1(4) . . ?
Br2 Hg1 N2 95.5(4) . . ?
C1 N1 C4 118.7(18) . . ?
C3 N2 C2 118(2) . . ?
C3 N2 Hg1 121.8(14) . . ?
C2 N2 Hg1 120.4(16) . . ?
C5 N3 C6 129.5(19) . . ?
C5 N3 H3A 115.2 . . ?
C6 N3 H3A 115.2 . . ?
N1 C1 C2 122.0(17) . . ?
N1 C1 H1 119.0 . . ?
C2 C1 H1 119.0 . . ?
N2 C2 C1 120(2) . . ?
N2 C2 H2 120.2 . . ?
C1 C2 H2 120.2 . . ?
N2 C3 C4 123(2) . . ?
N2 C3 H3 118.4 . . ?
C4 C3 H3 118.4 . . ?
N1 C4 C3 119(2) . . ?
N1 C4 C5 117.0(18) . . ?
C3 C4 C5 124.4(19) . . ?
O1 C5 N3 128(3) . . ?
O1 C5 C4 121(2) . . ?
N3 C5 C4 111.5(18) . . ?
C7 C6 N3 123.3(18) . . ?
C7 C6 C15 120(2) . . ?
N3 C6 C15 117.0(17) . . ?
C6 C7 C8 122.0(19) . . ?
C6 C7 H7 119.0 . . ?
C8 C7 H7 119.0 . . ?
C9 C8 C7 119(2) . . ?
C9 C8 H8 120.5 . . ?
C7 C8 H8 120.5 . . ?
C8 C9 C10 121(2) . . ?
C8 C9 Br3 117.5(18) . . ?
C10 C9 Br3 121.7(16) . . ?
C9 C10 C15 120.2(18) . . ?
C9 C10 C11 120(2) . . ?
C15 C10 C11 119(2) . . ?
C12 C11 C10 119(2) . . ?
C12 C11 H11 120.7 . . ?
C10 C11 H11 120.7 . . ?
C13 C12 C11 123(2) . . ?
C13 C12 H12 118.7 . . ?
C11 C12 H12 118.7 . . ?
C12 C13 C14 119(2) . . ?
C12 C13 H13 120.6 . . ?
C14 C13 H13 120.6 . . ?
C13 C14 C15 123(2) . . ?
C13 C14 H14 118.3 . . ?
C15 C14 H14 118.3 . . ?
C14 C15 C6 125(2) . . ?
C14 C15 C10 117.2(19) . . ?
C6 C15 C10 118.3(19) . . ?

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
Br1 Hg1 N2 C3 0.000(2) . . . . ?
Br2 Hg1 N2 C3 180.000(1) . . . . ?
Br1 Hg1 N2 C2 180.000(2) . . . . ?
Br2 Hg1 N2 C2 0.000(2) . . . . ?
C4 N1 C1 C2 0.000(3) . . . . ?
C3 N2 C2 C1 0.000(3) . . . . ?
Hg1 N2 C2 C1 180.000(2) . . . . ?
N1 C1 C2 N2 0.000(3) . . . . ?
C2 N2 C3 C4 0.000(2) . . . . ?
Hg1 N2 C3 C4 180.000(1) . . . . ?
C1 N1 C4 C3 0.000(2) . . . . ?
C1 N1 C4 C5 180.000(1) . . . . ?
N2 C3 C4 N1 0.000(2) . . . . ?
N2 C3 C4 C5 180.000(2) . . . . ?
C6 N3 C5 O1 0.0 . . . . ?
C6 N3 C5 C4 180.000(1) . . . . ?
N1 C4 C5 O1 180.000(1) . . . . ?
C3 C4 C5 O1 0.000(2) . . . . ?
N1 C4 C5 N3 0.000(1) . . . . ?
C3 C4 C5 N3 180.000(1) . . . . ?
C5 N3 C6 C7 0.000(1) . . . . ?
C5 N3 C6 C15 180.0 . . . . ?
N3 C6 C7 C8 180.000(2) . . . . ?
C15 C6 C7 C8 0.000(2) . . . . ?
C6 C7 C8 C9 0.000(3) . . . . ?
C7 C8 C9 C10 0.000(3) . . . . ?
C7 C8 C9 Br3 180.000(2) . . . . ?
C8 C9 C10 C15 0.000(3) . . . . ?
Br3 C9 C10 C15 180.000(2) . . . . ?
C8 C9 C10 C11 180.000(2) . . . . ?
Br3 C9 C10 C11 0.000(3) . . . . ?
C9 C10 C11 C12 180.000(2) . . . . ?
C15 C10 C11 C12 0.000(3) . . . . ?
C10 C11 C12 C13 0.000(3) . . . . ?
C11 C12 C13 C14 0.000(2) . . . . ?
C12 C13 C14 C15 0.000(2) . . . . ?
C13 C14 C15 C6 180.0 . . . . ?
C13 C14 C15 C10 0.000(1) . . . . ?
C7 C6 C15 C14 180.000(1) . . . . ?
N3 C6 C15 C14 0.000(1) . . . . ?
C7 C6 C15 C10 0.000(2) . . . . ?
N3 C6 C15 C10 180.000(2) . . . . ?
C9 C10 C15 C14 180.000(2) . . . . ?
C11 C10 C15 C14 0.000(2) . . . . ?
C9 C10 C15 C6 0.000(2) . . . . ?
C11 C10 C15 C6 180.000(2) . . . . ?

_diffrn_measured_fraction_theta_max 0.986
_diffrn_reflns_theta_full        29.25
_diffrn_measured_fraction_theta_full 0.986
_refine_diff_density_max         1.250
_refine_diff_density_min         -1.200
_refine_diff_density_rms         0.381

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
_geom_hbond_publ_flag
#
#D   H   A   D - H  H...A   D...A    D - H...A  symm(A)
#
N3 H3A N1 0.8600 2.1200 2.61(3) 115.00 . yes
C7 H7 O1 0.9300 2.3100 2.92(3) 123.00 . yes
C11 H11 Br2 0.9300 2.8400 3.64(2) 145.00 1_654 yes
C11 H11 Br3 0.9300 2.7100 3.14(2) 109.00 . yes
C11 H11 Br2 0.9300 2.8400 3.64(2) 145.00 4_664 yes
C14 H14 N3 0.9300 2.5300 2.84(2) 100.00 . yes
####################################################################### 
# 
# 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_shelxl
_database_code_depnum_ccdc_archive 'CCDC 1016901'
_audit_update_record             
;
2014-07-29 deposited with the CCDC.
2016-05-24 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C15 H10 Br1 Cl2 Hg1 N3 O1'
_chemical_formula_weight         599.65

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'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Hg Hg -2.3894 9.2266 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Br Br -0.2901 2.4595 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_symmetry_cell_setting           Triclinic
_symmetry_space_group_name_H-M   p-1

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

_cell_length_a                   7.8032(7)
_cell_length_b                   9.6586(9)
_cell_length_c                   11.4038(11)
_cell_angle_alpha                78.367(7)
_cell_angle_beta                 81.780(7)
_cell_angle_gamma                76.496(7)
_cell_volume                     814.39(13)
_cell_formula_units_Z            2
_cell_measurement_temperature    298(2)
_cell_measurement_reflns_used    11377
_cell_measurement_theta_min      2.61
_cell_measurement_theta_max      31.96

_exptl_crystal_description       Prism
_exptl_crystal_colour            'light violet'
_exptl_crystal_size_max          0.15
_exptl_crystal_size_mid          0.11
_exptl_crystal_size_min          0.10
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    2.445
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             556
_exptl_absorpt_coefficient_mu    12.236
_exptl_absorpt_correction_type   numerical
_exptl_absorpt_correction_T_min  0.218
_exptl_absorpt_correction_T_max  0.295
_exptl_absorpt_process_details   'shape of crystal determined optically'

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      298(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'STOE IPDS II'
_diffrn_measurement_method       'rotation method'
_diffrn_detector_area_resol_mean '0.15 mm'
_diffrn_standards_number         0
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            11377
_diffrn_reflns_av_R_equivalents  0.0475
_diffrn_reflns_av_sigmaI/netI    0.0549
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_theta_min         2.61
_diffrn_reflns_theta_max         31.96
_reflns_number_total             5550
_reflns_number_gt                3844
_reflns_threshold_expression     >2sigma(I)

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

_refine_special_details          
; 
 Refinement of F² against ALL reflections.  The weighted R-factor wR and 
 goodness of fit S are based on F², conventional R-factors R are based 
 on F, with F set to zero for negative F². The threshold expression of 
 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is 
 not relevant to the choice of reflections for refinement.  R-factors based 
 on F² are statistically about twice as large as those based on F, and R- 
 factors based on ALL data will be even larger. 
;

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0420P)²+0.3644P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         5550
_refine_ls_number_parameters     208
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0704
_refine_ls_R_factor_gt           0.0410
_refine_ls_wR_factor_ref         0.1101
_refine_ls_wR_factor_gt          0.1046
_refine_ls_goodness_of_fit_ref   1.191
_refine_ls_restrained_S_all      1.191
_refine_ls_shift/su_max          0.002
_refine_ls_shift/su_mean         0.001

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C 0.4764(9) 0.8933(7) 0.2938(6) 0.0429(15) Uani 1 1 d . . .
H1 H 0.5117 0.9783 0.2559 0.052 Uiso 1 1 calc R . .
C2 C 0.5319(9) 0.7698(7) 0.2394(6) 0.0410(14) Uani 1 1 d . . .
H2 H 0.6029 0.7747 0.1665 0.049 Uiso 1 1 calc R . .
C3 C 0.3824(8) 0.6433(6) 0.3943(5) 0.0330(12) Uani 1 1 d . . .
H3 H 0.3456 0.5588 0.4314 0.040 Uiso 1 1 calc R . .
C4 C 0.3294(8) 0.7645(6) 0.4486(5) 0.0305(11) Uani 1 1 d . . .
C5 C 0.2182(8) 0.7640(7) 0.5669(5) 0.0352(12) Uani 1 1 d . . .
C6 C 0.0493(8) 0.9412(6) 0.6936(5) 0.0309(11) Uani 1 1 d . . .
C7 C -0.0333(9) 0.8477(6) 0.7789(6) 0.0391(14) Uani 1 1 d . . .
H7 H -0.0196 0.7520 0.7700 0.047 Uiso 1 1 calc R . .
C8 C -0.1381(9) 0.8978(7) 0.8793(5) 0.0399(14) Uani 1 1 d . . .
H8 H -0.1958 0.8357 0.9358 0.048 Uiso 1 1 calc R . .
C9 C -0.1548(9) 1.0360(7) 0.8937(5) 0.0362(13) Uani 1 1 d . . .
C10 C -0.0725(8) 1.1375(6) 0.8100(5) 0.0308(11) Uani 1 1 d . . .
C11 C -0.0855(10) 1.2820(7) 0.8241(6) 0.0424(14) Uani 1 1 d . . .
H11 H -0.1478 1.3135 0.8930 0.051 Uiso 1 1 calc R . .
C12 C -0.0080(10) 1.3767(7) 0.7382(7) 0.0478(16) Uani 1 1 d . . .
H12 H -0.0180 1.4713 0.7490 0.057 Uiso 1 1 calc R . .
C13 C 0.0850(9) 1.3304(7) 0.6353(6) 0.0437(15) Uani 1 1 d . . .
H13 H 0.1354 1.3955 0.5769 0.052 Uiso 1 1 calc R . .
C14 C 0.1049(9) 1.1903(7) 0.6176(6) 0.0378(13) Uani 1 1 d . . .
H14 H 0.1678 1.1623 0.5476 0.045 Uiso 1 1 calc R . .
C15 C 0.0292(8) 1.0874(6) 0.7062(5) 0.0290(11) Uani 1 1 d . . .
N1 N 0.3764(8) 0.8920(6) 0.3966(5) 0.0403(12) Uani 1 1 d . . .
N2 N 0.4839(7) 0.6447(6) 0.2909(5) 0.0383(11) Uani 1 1 d . . .
N3 N 0.1542(7) 0.8957(5) 0.5919(4) 0.0348(11) Uani 1 1 d . . .
H3B H 0.1814 0.9645 0.5369 0.042 Uiso 1 1 calc R . .
O1 O 0.1925(7) 0.6490(5) 0.6301(4) 0.0473(11) Uani 1 1 d . . .
Hg1 Hg 0.56225(4) 0.43182(3) 0.18220(2) 0.04631(10) Uani 1 1 d . . .
Cl1 Cl 0.7316(3) 0.5404(2) 0.02456(17) 0.0629(5) Uani 1 1 d . . .
Cl2 Cl 0.4016(3) 0.2814(2) 0.30973(19) 0.0605(5) Uani 1 1 d . . .
Br1 Br -0.30540(10) 1.10044(8) 1.02803(6) 0.05018(18) Uani 1 1 d . . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
C1 N1 1.312(8) . ?
C1 C2 1.406(9) . ?
C1 H1 0.9300 . ?
C2 N2 1.344(8) . ?
C2 H2 0.9300 . ?
C3 N2 1.322(8) . ?
C3 C4 1.385(8) . ?
C3 H3 0.9300 . ?
C4 N1 1.362(7) . ?
C4 C5 1.496(8) . ?
C5 O1 1.239(7) . ?
C5 N3 1.325(8) . ?
C6 C7 1.384(8) . ?
C6 N3 1.405(7) . ?
C6 C15 1.419(7) . ?
C7 C8 1.409(8) . ?
C7 H7 0.9300 . ?
C8 C9 1.352(9) . ?
C8 H8 0.9300 . ?
C9 C10 1.423(8) . ?
C9 Br1 1.908(6) . ?
C10 C11 1.416(8) . ?
C10 C15 1.430(8) . ?
C11 C12 1.375(10) . ?
C11 H11 0.9300 . ?
C12 C13 1.385(10) . ?
C12 H12 0.9300 . ?
C13 C14 1.379(9) . ?
C13 H13 0.9300 . ?
C14 C15 1.434(8) . ?
C14 H14 0.9300 . ?
N2 Hg1 2.522(5) . ?
N3 H3B 0.8600 . ?
Hg1 Cl2 2.2967(19) . ?
Hg1 Cl1 2.2990(19) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
N1 C1 C2 121.8(6) . . ?
N1 C1 H1 119.1 . . ?
C2 C1 H1 119.1 . . ?
N2 C2 C1 121.1(6) . . ?
N2 C2 H2 119.4 . . ?
C1 C2 H2 119.4 . . ?
N2 C3 C4 121.8(5) . . ?
N2 C3 H3 119.1 . . ?
C4 C3 H3 119.1 . . ?
N1 C4 C3 121.4(5) . . ?
N1 C4 C5 116.0(5) . . ?
C3 C4 C5 122.5(5) . . ?
O1 C5 N3 126.5(5) . . ?
O1 C5 C4 120.7(5) . . ?
N3 C5 C4 112.8(5) . . ?
C7 C6 N3 121.7(5) . . ?
C7 C6 C15 120.5(5) . . ?
N3 C6 C15 117.8(5) . . ?
C6 C7 C8 119.9(5) . . ?
C6 C7 H7 120.1 . . ?
C8 C7 H7 120.1 . . ?
C9 C8 C7 120.1(6) . . ?
C9 C8 H8 119.9 . . ?
C7 C8 H8 119.9 . . ?
C8 C9 C10 122.9(5) . . ?
C8 C9 Br1 118.4(5) . . ?
C10 C9 Br1 118.6(4) . . ?
C11 C10 C9 124.0(5) . . ?
C11 C10 C15 119.2(5) . . ?
C9 C10 C15 116.8(5) . . ?
C12 C11 C10 121.4(6) . . ?
C12 C11 H11 119.3 . . ?
C10 C11 H11 119.3 . . ?
C11 C12 C13 119.6(6) . . ?
C11 C12 H12 120.2 . . ?
C13 C12 H12 120.2 . . ?
C14 C13 C12 121.6(6) . . ?
C14 C13 H13 119.2 . . ?
C12 C13 H13 119.2 . . ?
C13 C14 C15 120.5(6) . . ?
C13 C14 H14 119.7 . . ?
C15 C14 H14 119.7 . . ?
C6 C15 C10 119.7(5) . . ?
C6 C15 C14 122.7(5) . . ?
C10 C15 C14 117.5(5) . . ?
C1 N1 C4 116.7(5) . . ?
C3 N2 C2 117.1(5) . . ?
C3 N2 Hg1 122.3(4) . . ?
C2 N2 Hg1 120.3(4) . . ?
C5 N3 C6 130.5(5) . . ?
C5 N3 H3B 114.7 . . ?
C6 N3 H3B 114.7 . . ?
Cl2 Hg1 Cl1 165.81(7) . . ?
Cl2 Hg1 N2 99.16(13) . . ?
Cl1 Hg1 N2 94.81(13) . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
N1 C1 C2 N2 0.1(11) . . . . ?
N2 C3 C4 N1 1.5(9) . . . . ?
N2 C3 C4 C5 -178.5(6) . . . . ?
N1 C4 C5 O1 -168.4(6) . . . . ?
C3 C4 C5 O1 11.6(10) . . . . ?
N1 C4 C5 N3 12.2(8) . . . . ?
C3 C4 C5 N3 -167.8(6) . . . . ?
N3 C6 C7 C8 -179.7(6) . . . . ?
C15 C6 C7 C8 -0.1(10) . . . . ?
C6 C7 C8 C9 -1.4(11) . . . . ?
C7 C8 C9 C10 1.0(11) . . . . ?
C7 C8 C9 Br1 177.7(5) . . . . ?
C8 C9 C10 C11 -178.8(7) . . . . ?
Br1 C9 C10 C11 4.5(9) . . . . ?
C8 C9 C10 C15 0.9(9) . . . . ?
Br1 C9 C10 C15 -175.7(4) . . . . ?
C9 C10 C11 C12 -177.8(7) . . . . ?
C15 C10 C11 C12 2.5(10) . . . . ?
C10 C11 C12 C13 0.0(11) . . . . ?
C11 C12 C13 C14 -1.1(11) . . . . ?
C12 C13 C14 C15 -0.1(11) . . . . ?
C7 C6 C15 C10 2.1(9) . . . . ?
N3 C6 C15 C10 -178.3(5) . . . . ?
C7 C6 C15 C14 -176.9(6) . . . . ?
N3 C6 C15 C14 2.7(9) . . . . ?
C11 C10 C15 C6 177.3(6) . . . . ?
C9 C10 C15 C6 -2.4(8) . . . . ?
C11 C10 C15 C14 -3.6(9) . . . . ?
C9 C10 C15 C14 176.6(6) . . . . ?
C13 C14 C15 C6 -178.5(6) . . . . ?
C13 C14 C15 C10 2.5(9) . . . . ?
C2 C1 N1 C4 0.4(10) . . . . ?
C3 C4 N1 C1 -1.1(9) . . . . ?
C5 C4 N1 C1 178.9(6) . . . . ?
C4 C3 N2 C2 -1.0(9) . . . . ?
C4 C3 N2 Hg1 -175.1(4) . . . . ?
C1 C2 N2 C3 0.2(10) . . . . ?
C1 C2 N2 Hg1 174.4(5) . . . . ?
O1 C5 N3 C6 2.4(12) . . . . ?
C4 C5 N3 C6 -178.2(6) . . . . ?
C7 C6 N3 C5 -12.6(11) . . . . ?
C15 C6 N3 C5 167.8(6) . . . . ?
C3 N2 Hg1 Cl2 2.5(5) . . . . ?
C2 N2 Hg1 Cl2 -171.4(5) . . . . ?
C3 N2 Hg1 Cl1 -179.9(5) . . . . ?
C2 N2 Hg1 Cl1 6.1(5) . . . . ?

_diffrn_measured_fraction_theta_max 0.986
_diffrn_reflns_theta_full        31.96
_diffrn_measured_fraction_theta_full 0.986
_refine_diff_density_max         0.963
_refine_diff_density_min         -0.842
_refine_diff_density_rms         0.143
####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_d:\determination\solution\c-test7\c-test7
_database_code_depnum_ccdc_archive 'CCDC 1016902'
_audit_update_record             
;
2014-07-29 deposited with the CCDC.
2016-05-24 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C15 H10 Br1 N3 O1'
_chemical_formula_weight         328.16

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Hg Hg -2.3894 9.2266 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Br Br -0.2901 2.4595 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_symmetry_cell_setting           Monoclinic
_symmetry_space_group_name_H-M   P21/n

loop_
_symmetry_equiv_pos_as_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                   5.1029(7)
_cell_length_b                   13.9355(14)
_cell_length_c                   18.293(3)
_cell_angle_alpha                90.00
_cell_angle_beta                 92.318(11)
_cell_angle_gamma                90.00
_cell_volume                     1299.7(3)
_cell_formula_units_Z            4
_cell_measurement_temperature    298(2)
_cell_measurement_reflns_used    18467
_cell_measurement_theta_min      2.23
_cell_measurement_theta_max      32.23

_exptl_crystal_description       Block
_exptl_crystal_colour            Yellow
_exptl_crystal_size_max          0.35
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.18
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.677
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             656
_exptl_absorpt_coefficient_mu    3.160
_exptl_absorpt_correction_type   numerical
_exptl_absorpt_correction_T_min  0.475
_exptl_absorpt_correction_T_max  0.568
_exptl_absorpt_process_details   'shape of crystal determined optically'

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      298(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'STOE IPDS II'
_diffrn_measurement_method       'rotation method'
_diffrn_detector_area_resol_mean '0.15 mm'
_diffrn_standards_number         0
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            18467
_diffrn_reflns_av_R_equivalents  0.1001
_diffrn_reflns_av_sigmaI/netI    0.1186
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_k_min       -20
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_l_min       -27
_diffrn_reflns_limit_l_max       24
_diffrn_reflns_theta_min         2.23
_diffrn_reflns_theta_max         32.23
_reflns_number_total             4477
_reflns_number_gt                2587
_reflns_threshold_expression     >2sigma(I)

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

_refine_special_details          
; 
 Refinement of F² against ALL reflections.  The weighted R-factor wR and 
 goodness of fit S are based on F², conventional R-factors R are based 
 on F, with F set to zero for negative F². The threshold expression of 
 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is 
 not relevant to the choice of reflections for refinement.  R-factors based 
 on F² are statistically about twice as large as those based on F, and R- 
 factors based on ALL data will be even larger. 
;

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0344P)²+2.7624P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         4477
_refine_ls_number_parameters     181
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0910
_refine_ls_R_factor_gt           0.0850
_refine_ls_wR_factor_ref         0.1962
_refine_ls_wR_factor_gt          0.1569
_refine_ls_goodness_of_fit_ref   1.194
_refine_ls_restrained_S_all      1.194
_refine_ls_shift/su_max          0.005
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C 1.6003(13) 0.9306(5) 0.1206(4) 0.0537(15) Uani 1 1 d . . .
H1 H 1.6185 0.9667 0.1633 0.064 Uiso 1 1 calc R . .
C2 C 1.7626(12) 0.9497(5) 0.0635(4) 0.0516(15) Uani 1 1 d . . .
H2 H 1.8853 0.9988 0.0686 0.062 Uiso 1 1 calc R . .
C3 C 1.5683(12) 0.8307(5) -0.0027(3) 0.0485(14) Uani 1 1 d . . .
H3 H 1.5531 0.7935 -0.0448 0.058 Uiso 1 1 calc R . .
C4 C 1.4037(10) 0.8130(4) 0.0540(3) 0.0356(11) Uani 1 1 d . . .
C5 C 1.2067(11) 0.7332(4) 0.0468(3) 0.0376(11) Uani 1 1 d . . .
C6 C 0.8756(10) 0.6521(4) 0.1242(3) 0.0344(11) Uani 1 1 d . . .
C7 C 0.8018(12) 0.5816(4) 0.0757(3) 0.0441(13) Uani 1 1 d . . .
H7 H 0.8771 0.5785 0.0303 0.053 Uiso 1 1 calc R . .
C8 C 0.6119(12) 0.5138(4) 0.0945(3) 0.0469(14) Uani 1 1 d . . .
H8 H 0.5655 0.4651 0.0617 0.056 Uiso 1 1 calc R . .
C9 C 0.4950(10) 0.5185(4) 0.1599(3) 0.0435(13) Uani 1 1 d . . .
C10 C 0.5609(10) 0.5905(4) 0.2119(3) 0.0394(12) Uani 1 1 d . . .
C11 C 0.4484(12) 0.5988(5) 0.2816(4) 0.0550(17) Uani 1 1 d . . .
H11 H 0.3231 0.5542 0.2948 0.066 Uiso 1 1 calc R . .
C12 C 0.5189(13) 0.6702(5) 0.3297(4) 0.0577(17) Uani 1 1 d . . .
H12 H 0.4393 0.6745 0.3744 0.069 Uiso 1 1 calc R . .
C13 C 0.7091(13) 0.7361(5) 0.3118(3) 0.0512(15) Uani 1 1 d . . .
H13 H 0.7577 0.7846 0.3446 0.061 Uiso 1 1 calc R . .
C14 C 0.8250(11) 0.7300(4) 0.2460(3) 0.0429(13) Uani 1 1 d . . .
H14 H 0.9539 0.7744 0.2353 0.051 Uiso 1 1 calc R . .
C15 C 0.7573(10) 0.6589(4) 0.1937(3) 0.0335(11) Uani 1 1 d . . .
N1 N 1.4194(9) 0.8621(4) 0.1161(3) 0.0460(12) Uani 1 1 d . . .
N2 N 1.7483(10) 0.9000(4) 0.0018(3) 0.0548(14) Uani 1 1 d . . .
N3 N 1.0717(9) 0.7195(3) 0.1091(2) 0.0383(10) Uani 1 1 d . . .
H3B H 1.1130 0.7580 0.1445 0.046 Uiso 1 1 calc R . .
O1 O 1.1701(10) 0.6884(4) -0.0097(2) 0.0608(13) Uani 1 1 d . . .
Br1 Br 0.23839(13) 0.42434(5) 0.18119(5) 0.0645(3) Uani 1 1 d . . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
C1 N1 1.328(7) . ?
C1 C2 1.385(9) . ?
C1 H1 0.9300 . ?
C2 N2 1.323(8) . ?
C2 H2 0.9300 . ?
C3 N2 1.333(8) . ?
C3 C4 1.383(7) . ?
C3 H3 0.9300 . ?
C4 N1 1.326(7) . ?
C4 C5 1.501(7) . ?
C5 O1 1.215(7) . ?
C5 N3 1.370(7) . ?
C6 C7 1.366(8) . ?
C6 N3 1.408(6) . ?
C6 C15 1.432(7) . ?
C7 C8 1.406(8) . ?
C7 H7 0.9300 . ?
C8 C9 1.361(9) . ?
C8 H8 0.9300 . ?
C9 C10 1.414(9) . ?
C9 Br1 1.905(5) . ?
C10 C11 1.423(8) . ?
C10 C15 1.433(7) . ?
C11 C12 1.367(10) . ?
C11 H11 0.9300 . ?
C12 C13 1.385(10) . ?
C12 H12 0.9300 . ?
C13 C14 1.365(8) . ?
C13 H13 0.9300 . ?
C14 C15 1.411(8) . ?
C14 H14 0.9300 . ?
N3 H3B 0.8600 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
N1 C1 C2 121.8(6) . . ?
N1 C1 H1 119.1 . . ?
C2 C1 H1 119.1 . . ?
N2 C2 C1 122.0(6) . . ?
N2 C2 H2 119.0 . . ?
C1 C2 H2 119.0 . . ?
N2 C3 C4 121.5(6) . . ?
N2 C3 H3 119.3 . . ?
C4 C3 H3 119.3 . . ?
N1 C4 C3 122.1(5) . . ?
N1 C4 C5 118.4(4) . . ?
C3 C4 C5 119.4(5) . . ?
O1 C5 N3 124.9(5) . . ?
O1 C5 C4 122.3(5) . . ?
N3 C5 C4 112.8(4) . . ?
C7 C6 N3 122.1(5) . . ?
C7 C6 C15 120.6(5) . . ?
N3 C6 C15 117.3(5) . . ?
C6 C7 C8 120.0(5) . . ?
C6 C7 H7 120.0 . . ?
C8 C7 H7 120.0 . . ?
C9 C8 C7 120.9(5) . . ?
C9 C8 H8 119.6 . . ?
C7 C8 H8 119.6 . . ?
C8 C9 C10 121.7(5) . . ?
C8 C9 Br1 118.4(5) . . ?
C10 C9 Br1 119.9(4) . . ?
C9 C10 C11 124.5(5) . . ?
C9 C10 C15 117.7(5) . . ?
C11 C10 C15 117.8(5) . . ?
C12 C11 C10 122.0(6) . . ?
C12 C11 H11 119.0 . . ?
C10 C11 H11 119.0 . . ?
C11 C12 C13 120.0(6) . . ?
C11 C12 H12 120.0 . . ?
C13 C12 H12 120.0 . . ?
C14 C13 C12 119.9(6) . . ?
C14 C13 H13 120.0 . . ?
C12 C13 H13 120.0 . . ?
C13 C14 C15 122.7(6) . . ?
C13 C14 H14 118.7 . . ?
C15 C14 H14 118.7 . . ?
C14 C15 C6 123.3(5) . . ?
C14 C15 C10 117.6(5) . . ?
C6 C15 C10 119.1(5) . . ?
C4 N1 C1 116.3(5) . . ?
C2 N2 C3 116.4(5) . . ?
C5 N3 C6 129.9(4) . . ?
C5 N3 H3B 115.0 . . ?
C6 N3 H3B 115.0 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
N1 C1 C2 N2 -0.8(11) . . . . ?
N2 C3 C4 N1 -1.5(10) . . . . ?
N2 C3 C4 C5 -179.2(6) . . . . ?
N1 C4 C5 O1 175.8(6) . . . . ?
C3 C4 C5 O1 -6.5(9) . . . . ?
N1 C4 C5 N3 -2.4(7) . . . . ?
C3 C4 C5 N3 175.4(5) . . . . ?
N3 C6 C7 C8 177.6(5) . . . . ?
C15 C6 C7 C8 -1.3(8) . . . . ?
C6 C7 C8 C9 1.5(9) . . . . ?
C7 C8 C9 C10 -0.7(9) . . . . ?
C7 C8 C9 Br1 179.7(4) . . . . ?
C8 C9 C10 C11 -179.3(6) . . . . ?
Br1 C9 C10 C11 0.3(8) . . . . ?
C8 C9 C10 C15 -0.3(8) . . . . ?
Br1 C9 C10 C15 179.3(4) . . . . ?
C9 C10 C11 C12 -179.7(6) . . . . ?
C15 C10 C11 C12 1.3(9) . . . . ?
C10 C11 C12 C13 -1.3(10) . . . . ?
C11 C12 C13 C14 0.3(10) . . . . ?
C12 C13 C14 C15 0.8(9) . . . . ?
C13 C14 C15 C6 179.4(5) . . . . ?
C13 C14 C15 C10 -0.8(8) . . . . ?
C7 C6 C15 C14 -180.0(5) . . . . ?
N3 C6 C15 C14 1.1(7) . . . . ?
C7 C6 C15 C10 0.3(8) . . . . ?
N3 C6 C15 C10 -178.7(5) . . . . ?
C9 C10 C15 C14 -179.3(5) . . . . ?
C11 C10 C15 C14 -0.2(7) . . . . ?
C9 C10 C15 C6 0.5(7) . . . . ?
C11 C10 C15 C6 179.6(5) . . . . ?
C3 C4 N1 C1 0.9(9) . . . . ?
C5 C4 N1 C1 178.6(5) . . . . ?
C2 C1 N1 C4 0.2(10) . . . . ?
C1 C2 N2 C3 0.2(10) . . . . ?
C4 C3 N2 C2 0.9(10) . . . . ?
O1 C5 N3 C6 2.7(10) . . . . ?
C4 C5 N3 C6 -179.3(5) . . . . ?
C7 C6 N3 C5 4.9(9) . . . . ?
C15 C6 N3 C5 -176.2(5) . . . . ?

_diffrn_measured_fraction_theta_max 0.990
_diffrn_reflns_theta_full        32.23
_diffrn_measured_fraction_theta_full 0.990
_refine_diff_density_max         0.643
_refine_diff_density_min         -0.669
_refine_diff_density_rms         0.097
####################################################################### 
# 
# 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_c:\determination\solution\c-test6\c-test6
_database_code_depnum_ccdc_archive 'CCDC 1016903'
_audit_update_record             
;
2014-07-29 deposited with the CCDC.
2016-05-24 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C15 H10 Cl1 N3 O1'
_chemical_formula_weight         283.71

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_symmetry_cell_setting           Monoclinic
_symmetry_space_group_name_H-M   P21/n

loop_
_symmetry_equiv_pos_as_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                   5.0499(7)
_cell_length_b                   13.8172(11)
_cell_length_c                   18.221(2)
_cell_angle_alpha                90.00
_cell_angle_beta                 93.432(10)
_cell_angle_gamma                90.00
_cell_volume                     1269.1(3)
_cell_formula_units_Z            4
_cell_measurement_temperature    298(2)
_cell_measurement_reflns_used    13735
_cell_measurement_theta_min      2.24
_cell_measurement_theta_max      29.19

_exptl_crystal_description       Block
_exptl_crystal_colour            Colorless
_exptl_crystal_size_max          0.40
_exptl_crystal_size_mid          0.10
_exptl_crystal_size_min          0.08
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.485
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             584
_exptl_absorpt_coefficient_mu    0.299
_exptl_absorpt_correction_type   numerical
_exptl_absorpt_correction_T_min  0.966
_exptl_absorpt_correction_T_max  0.977
_exptl_absorpt_process_details   'shape of crystal determined optically'

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      298(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'STOE IPDS II'
_diffrn_measurement_method       'rotation method'
_diffrn_detector_area_resol_mean '0.15 mm'
_diffrn_standards_number         0
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            13735
_diffrn_reflns_av_R_equivalents  0.1001
_diffrn_reflns_av_sigmaI/netI    0.0678
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_l_min       -24
_diffrn_reflns_limit_l_max       24
_diffrn_reflns_theta_min         2.24
_diffrn_reflns_theta_max         29.19
_reflns_number_total             3416
_reflns_number_gt                2063
_reflns_threshold_expression     >2sigma(I)

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

_refine_special_details          
; 
 Refinement of F² against ALL reflections.  The weighted R-factor wR and 
 goodness of fit S are based on F², conventional R-factors R are based 
 on F, with F set to zero for negative F². The threshold expression of 
 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is 
 not relevant to the choice of reflections for refinement.  R-factors based 
 on F² are statistically about twice as large as those based on F, and R- 
 factors based on ALL data will be even larger. 
;

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0302P)²+0.7376P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     SHELXL
_refine_ls_extinction_coef       0.0071(13)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_number_reflns         3416
_refine_ls_number_parameters     182
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1609
_refine_ls_R_factor_gt           0.0989
_refine_ls_wR_factor_ref         0.1555
_refine_ls_wR_factor_gt          0.1368
_refine_ls_goodness_of_fit_ref   1.201
_refine_ls_restrained_S_all      1.201
_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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C 1.6005(7) 0.0672(3) 0.1202(2) 0.0595(10) Uani 1 1 d . . .
H1 H 1.6194 0.0291 0.1623 0.071 Uiso 1 1 calc R . .
C2 C 1.7622(7) 0.0500(3) 0.0635(2) 0.0550(9) Uani 1 1 d . . .
H2 H 1.8870 0.0006 0.0686 0.066 Uiso 1 1 calc R . .
C3 C 1.5641(7) 0.1710(3) -0.00142(19) 0.0553(9) Uani 1 1 d . . .
H3 H 1.5473 0.2093 -0.0434 0.066 Uiso 1 1 calc R . .
C4 C 1.3987(6) 0.1889(2) 0.05503(17) 0.0427(7) Uani 1 1 d . . .
C5 C 1.1991(7) 0.2686(2) 0.04861(18) 0.0455(8) Uani 1 1 d . . .
C6 C 0.8740(6) 0.3500(2) 0.12671(16) 0.0419(7) Uani 1 1 d . . .
C7 C 0.7993(7) 0.4230(3) 0.07903(19) 0.0523(9) Uani 1 1 d . . .
H7 H 0.8758 0.4280 0.0340 0.063 Uiso 1 1 calc R . .
C8 C 0.6065(8) 0.4904(3) 0.0983(2) 0.0568(9) Uani 1 1 d . . .
H8 H 0.5575 0.5403 0.0660 0.068 Uiso 1 1 calc R . .
C9 C 0.4917(7) 0.4835(3) 0.1633(2) 0.0536(9) Uani 1 1 d . . .
C10 C 0.5593(6) 0.4091(2) 0.21414(18) 0.0464(8) Uani 1 1 d . . .
C11 C 0.4407(7) 0.3986(3) 0.2826(2) 0.0635(11) Uani 1 1 d . . .
H11 H 0.3121 0.4427 0.2955 0.076 Uiso 1 1 calc R . .
C12 C 0.5119(8) 0.3255(3) 0.3296(2) 0.0663(11) Uani 1 1 d . . .
H12 H 0.4329 0.3204 0.3742 0.080 Uiso 1 1 calc R . .
C13 C 0.7011(8) 0.2584(3) 0.3115(2) 0.0604(10) Uani 1 1 d . . .
H13 H 0.7472 0.2082 0.3438 0.072 Uiso 1 1 calc R . .
C14 C 0.8195(7) 0.2656(3) 0.24660(17) 0.0486(8) Uani 1 1 d . . .
H14 H 0.9465 0.2200 0.2354 0.058 Uiso 1 1 calc R . .
C15 C 0.7546(6) 0.3405(2) 0.19573(17) 0.0414(7) Uani 1 1 d . . .
N1 N 1.4176(6) 0.1369(2) 0.11669(15) 0.0514(7) Uani 1 1 d . . .
N2 N 1.7467(6) 0.1011(2) 0.00213(17) 0.0608(8) Uani 1 1 d . . .
N3 N 1.0709(5) 0.28194(19) 0.11116(14) 0.0458(7) Uani 1 1 d . . .
H3B H 1.1165 0.2431 0.1466 0.055 Uiso 1 1 calc R . .
O1 O 1.1608(5) 0.3152(2) -0.00777(13) 0.0671(8) Uani 1 1 d . . .
Cl1 Cl 0.2545(2) 0.56963(8) 0.18442(7) 0.0783(4) Uani 1 1 d . . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
C1 N1 1.334(4) . ?
C1 C2 1.376(5) . ?
C1 H1 0.9300 . ?
C2 N2 1.321(4) . ?
C2 H2 0.9300 . ?
C3 N2 1.335(4) . ?
C3 C4 1.386(4) . ?
C3 H3 0.9300 . ?
C4 N1 1.332(4) . ?
C4 C5 1.493(5) . ?
C5 O1 1.218(4) . ?
C5 N3 1.357(4) . ?
C6 C7 1.370(5) . ?
C6 N3 1.409(4) . ?
C6 C15 1.433(4) . ?
C7 C8 1.407(5) . ?
C7 H7 0.9300 . ?
C8 C9 1.352(5) . ?
C8 H8 0.9300 . ?
C9 C10 1.412(5) . ?
C9 Cl1 1.748(4) . ?
C10 C15 1.423(4) . ?
C10 C11 1.423(5) . ?
C11 C12 1.359(6) . ?
C11 H11 0.9300 . ?
C12 C13 1.385(5) . ?
C12 H12 0.9300 . ?
C13 C14 1.360(5) . ?
C13 H13 0.9300 . ?
C14 C15 1.415(4) . ?
C14 H14 0.9300 . ?
N3 H3B 0.8600 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
N1 C1 C2 121.9(3) . . ?
N1 C1 H1 119.0 . . ?
C2 C1 H1 119.0 . . ?
N2 C2 C1 122.4(3) . . ?
N2 C2 H2 118.8 . . ?
C1 C2 H2 118.8 . . ?
N2 C3 C4 122.6(3) . . ?
N2 C3 H3 118.7 . . ?
C4 C3 H3 118.7 . . ?
N1 C4 C3 120.9(3) . . ?
N1 C4 C5 118.5(3) . . ?
C3 C4 C5 120.5(3) . . ?
O1 C5 N3 125.3(3) . . ?
O1 C5 C4 121.9(3) . . ?
N3 C5 C4 112.8(3) . . ?
C7 C6 N3 122.3(3) . . ?
C7 C6 C15 120.6(3) . . ?
N3 C6 C15 117.0(3) . . ?
C6 C7 C8 119.9(3) . . ?
C6 C7 H7 120.1 . . ?
C8 C7 H7 120.1 . . ?
C9 C8 C7 120.7(3) . . ?
C9 C8 H8 119.6 . . ?
C7 C8 H8 119.6 . . ?
C8 C9 C10 121.8(3) . . ?
C8 C9 Cl1 118.7(3) . . ?
C10 C9 Cl1 119.5(3) . . ?
C9 C10 C15 118.3(3) . . ?
C9 C10 C11 123.5(3) . . ?
C15 C10 C11 118.2(3) . . ?
C12 C11 C10 121.2(4) . . ?
C12 C11 H11 119.4 . . ?
C10 C11 H11 119.4 . . ?
C11 C12 C13 120.6(4) . . ?
C11 C12 H12 119.7 . . ?
C13 C12 H12 119.7 . . ?
C14 C13 C12 120.2(4) . . ?
C14 C13 H13 119.9 . . ?
C12 C13 H13 119.9 . . ?
C13 C14 C15 121.8(3) . . ?
C13 C14 H14 119.1 . . ?
C15 C14 H14 119.1 . . ?
C14 C15 C10 118.0(3) . . ?
C14 C15 C6 123.3(3) . . ?
C10 C15 C6 118.7(3) . . ?
C4 N1 C1 116.4(3) . . ?
C2 N2 C3 115.7(3) . . ?
C5 N3 C6 129.6(3) . . ?
C5 N3 H3B 115.2 . . ?
C6 N3 H3B 115.2 . . ?

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
N1 C1 C2 N2 -0.1(6) . . . . ?
N2 C3 C4 N1 0.9(6) . . . . ?
N2 C3 C4 C5 179.5(3) . . . . ?
N1 C4 C5 O1 -175.6(3) . . . . ?
C3 C4 C5 O1 5.8(5) . . . . ?
N1 C4 C5 N3 4.3(4) . . . . ?
C3 C4 C5 N3 -174.3(3) . . . . ?
N3 C6 C7 C8 -178.3(3) . . . . ?
C15 C6 C7 C8 1.0(5) . . . . ?
C6 C7 C8 C9 -0.6(6) . . . . ?
C7 C8 C9 C10 0.0(6) . . . . ?
C7 C8 C9 Cl1 179.7(3) . . . . ?
C8 C9 C10 C15 0.2(5) . . . . ?
Cl1 C9 C10 C15 -179.5(2) . . . . ?
C8 C9 C10 C11 -179.2(3) . . . . ?
Cl1 C9 C10 C11 1.1(5) . . . . ?
C9 C10 C11 C12 179.7(4) . . . . ?
C15 C10 C11 C12 0.3(5) . . . . ?
C10 C11 C12 C13 -0.6(6) . . . . ?
C11 C12 C13 C14 0.6(6) . . . . ?
C12 C13 C14 C15 -0.2(6) . . . . ?
C13 C14 C15 C10 -0.1(5) . . . . ?
C13 C14 C15 C6 -179.6(3) . . . . ?
C9 C10 C15 C14 -179.3(3) . . . . ?
C11 C10 C15 C14 0.1(5) . . . . ?
C9 C10 C15 C6 0.2(4) . . . . ?
C11 C10 C15 C6 179.6(3) . . . . ?
C7 C6 C15 C14 178.7(3) . . . . ?
N3 C6 C15 C14 -1.9(5) . . . . ?
C7 C6 C15 C10 -0.8(5) . . . . ?
N3 C6 C15 C10 178.6(3) . . . . ?
C3 C4 N1 C1 -0.7(5) . . . . ?
C5 C4 N1 C1 -179.3(3) . . . . ?
C2 C1 N1 C4 0.3(5) . . . . ?
C1 C2 N2 C3 0.2(6) . . . . ?
C4 C3 N2 C2 -0.6(5) . . . . ?
O1 C5 N3 C6 -0.9(6) . . . . ?
C4 C5 N3 C6 179.1(3) . . . . ?
C7 C6 N3 C5 -6.9(5) . . . . ?
C15 C6 N3 C5 173.8(3) . . . . ?

_diffrn_measured_fraction_theta_max 0.997
_diffrn_reflns_theta_full        29.19
_diffrn_measured_fraction_theta_full 0.997
_refine_diff_density_max         0.196
_refine_diff_density_min         -0.246
_refine_diff_density_rms         0.048
####################################################################### 
# 
# 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_c:\determination\solution\489\kh489
_database_code_depnum_ccdc_archive 'CCDC 1016904'
_audit_update_record             
;
2014-07-29 deposited with the CCDC.
2016-05-24 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C15 H10 Cl1 Hg1 I2 N3 O1'
_chemical_formula_weight         738.10

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Hg Hg -2.3894 9.2266 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
I I -0.4742 1.8119 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_symmetry_cell_setting           Triclinic
_symmetry_space_group_name_H-M   P-1

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

_cell_length_a                   8.5716(7)
_cell_length_b                   9.8507(9)
_cell_length_c                   11.6901(10)
_cell_angle_alpha                103.615(7)
_cell_angle_beta                 103.475(7)
_cell_angle_gamma                102.305(7)
_cell_volume                     894.64(13)
_cell_formula_units_Z            2
_cell_measurement_temperature    298(2)
_cell_measurement_reflns_used    10009
_cell_measurement_theta_min      1.88
_cell_measurement_theta_max      29.23

_exptl_crystal_description       Block
_exptl_crystal_colour            Yellow
_exptl_crystal_size_max          0.30
_exptl_crystal_size_mid          0.25
_exptl_crystal_size_min          0.17
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    2.740
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             664
_exptl_absorpt_coefficient_mu    12.208
_exptl_absorpt_correction_type   numerical
_exptl_absorpt_correction_T_min  0.0401
_exptl_absorpt_correction_T_max  0.1300
_exptl_absorpt_process_details   'shape of crystal determined optically'

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      298(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'STOE IPDS II'
_diffrn_measurement_method       'rotation method'
_diffrn_detector_area_resol_mean '0.15 mm'
_diffrn_standards_number         0
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            10009
_diffrn_reflns_av_R_equivalents  0.1147
_diffrn_reflns_av_sigmaI/netI    0.0824
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_theta_min         1.88
_diffrn_reflns_theta_max         29.23
_reflns_number_total             4799
_reflns_number_gt                3786
_reflns_threshold_expression     >2sigma(I)

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

_refine_special_details          
; 
 Refinement of F² against ALL reflections.  The weighted R-factor wR and 
 goodness of fit S are based on F², conventional R-factors R are based 
 on F, with F set to zero for negative F². The threshold expression of 
 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is 
 not relevant to the choice of reflections for refinement.  R-factors based 
 on F² are statistically about twice as large as those based on F, and R- 
 factors based on ALL data will be even larger. 
;

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.1347P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         4799
_refine_ls_number_parameters     208
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0914
_refine_ls_R_factor_gt           0.0763
_refine_ls_wR_factor_ref         0.2029
_refine_ls_wR_factor_gt          0.1888
_refine_ls_goodness_of_fit_ref   1.044
_refine_ls_restrained_S_all      1.044
_refine_ls_shift/su_max          0.005
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C 0.1318(14) -0.2433(11) 0.2548(10) 0.046(2) Uani 1 1 d . . .
H1 H 0.1783 -0.3045 0.2928 0.056 Uiso 1 1 calc R . .
C2 C 0.2050(15) -0.0945(12) 0.3019(10) 0.048(2) Uani 1 1 d . . .
H2 H 0.2988 -0.0586 0.3710 0.058 Uiso 1 1 calc R . .
C3 C 0.0087(13) -0.0582(10) 0.1500(9) 0.042(2) Uani 1 1 d . . .
H3 H -0.0368 0.0024 0.1107 0.050 Uiso 1 1 calc R . .
C4 C -0.0631(11) -0.2099(10) 0.1051(8) 0.0347(17) Uani 1 1 d . . .
C5 C -0.2135(12) -0.2724(10) -0.0077(8) 0.0353(17) Uani 1 1 d . . .
C6 C -0.4201(12) -0.5175(11) -0.1206(8) 0.0377(18) Uani 1 1 d . . .
C7 C -0.5305(13) -0.4719(11) -0.1978(9) 0.042(2) Uani 1 1 d . . .
H7 H -0.5153 -0.3731 -0.1881 0.050 Uiso 1 1 calc R . .
C8 C -0.6680(13) -0.5768(12) -0.2923(10) 0.044(2) Uani 1 1 d . . .
H8 H -0.7422 -0.5470 -0.3460 0.053 Uiso 1 1 calc R . .
C9 C -0.6911(13) -0.7219(13) -0.3044(9) 0.046(2) Uani 1 1 d . . .
C10 C -0.5850(13) -0.7717(11) -0.2248(8) 0.0399(19) Uani 1 1 d . . .
C11 C -0.6111(16) -0.9234(12) -0.2331(11) 0.052(3) Uani 1 1 d . . .
H11 H -0.7015 -0.9929 -0.2942 0.063 Uiso 1 1 calc R . .
C12 C -0.5049(18) -0.9658(12) -0.1523(11) 0.055(3) Uani 1 1 d . . .
H12 H -0.5216 -1.0643 -0.1597 0.066 Uiso 1 1 calc R . .
C13 C -0.3723(19) -0.8641(13) -0.0595(12) 0.058(3) Uani 1 1 d . . .
H13 H -0.3038 -0.8947 -0.0026 0.069 Uiso 1 1 calc R . .
C14 C -0.3398(15) -0.7191(11) -0.0495(10) 0.047(2) Uani 1 1 d . . .
H14 H -0.2464 -0.6532 0.0115 0.057 Uiso 1 1 calc R . .
C15 C -0.4451(13) -0.6678(10) -0.1298(9) 0.0385(19) Uani 1 1 d . . .
N1 N -0.0035(12) -0.3017(9) 0.1566(8) 0.0432(18) Uani 1 1 d . . .
N2 N 0.1452(11) -0.0007(9) 0.2513(9) 0.0442(18) Uani 1 1 d . . .
N3 N -0.2787(11) -0.4165(9) -0.0273(8) 0.0409(17) Uani 1 1 d . . .
H3B H -0.2264 -0.4523 0.0249 0.049 Uiso 1 1 calc R . .
O1 O -0.2637(10) -0.1990(8) -0.0704(7) 0.0518(19) Uani 1 1 d . . .
Hg1 Hg 0.26856(5) 0.27387(5) 0.34242(4) 0.04879(17) Uani 1 1 d . . .
Cl1 Cl -0.8594(4) -0.8434(4) -0.4250(3) 0.0597(7) Uani 1 1 d . . .
I1 I -0.00337(12) 0.34784(10) 0.27342(10) 0.0717(3) Uani 1 1 d . . .
I2 I 0.56977(9) 0.28225(8) 0.45905(7) 0.0534(2) Uani 1 1 d . . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
C1 N1 1.334(13) . ?
C1 C2 1.383(15) . ?
C1 H1 0.9300 . ?
C2 N2 1.336(13) . ?
C2 H2 0.9300 . ?
C3 N2 1.359(12) . ?
C3 C4 1.405(12) . ?
C3 H3 0.9300 . ?
C4 N1 1.323(12) . ?
C4 C5 1.506(12) . ?
C5 O1 1.217(11) . ?
C5 N3 1.352(12) . ?
C6 C7 1.372(13) . ?
C6 N3 1.417(12) . ?
C6 C15 1.425(13) . ?
C7 C8 1.420(14) . ?
C7 H7 0.9300 . ?
C8 C9 1.369(16) . ?
C8 H8 0.9300 . ?
C9 C10 1.394(16) . ?
C9 Cl1 1.739(10) . ?
C10 C15 1.428(14) . ?
C10 C11 1.440(15) . ?
C11 C12 1.358(19) . ?
C11 H11 0.9300 . ?
C12 C13 1.379(19) . ?
C12 H12 0.9300 . ?
C13 C14 1.367(15) . ?
C13 H13 0.9300 . ?
C14 C15 1.406(15) . ?
C14 H14 0.9300 . ?
N2 Hg1 2.544(8) . ?
N3 H3B 0.8600 . ?
Hg1 I1 2.5959(9) . ?
Hg1 I2 2.5976(8) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
N1 C1 C2 122.0(10) . . ?
N1 C1 H1 119.0 . . ?
C2 C1 H1 119.0 . . ?
N2 C2 C1 122.0(10) . . ?
N2 C2 H2 119.0 . . ?
C1 C2 H2 119.0 . . ?
N2 C3 C4 119.5(9) . . ?
N2 C3 H3 120.2 . . ?
C4 C3 H3 120.2 . . ?
N1 C4 C3 123.0(9) . . ?
N1 C4 C5 117.9(8) . . ?
C3 C4 C5 119.1(8) . . ?
O1 C5 N3 126.8(9) . . ?
O1 C5 C4 122.5(8) . . ?
N3 C5 C4 110.7(8) . . ?
C7 C6 N3 121.2(9) . . ?
C7 C6 C15 121.3(9) . . ?
N3 C6 C15 117.5(8) . . ?
C6 C7 C8 119.5(9) . . ?
C6 C7 H7 120.3 . . ?
C8 C7 H7 120.3 . . ?
C9 C8 C7 119.9(9) . . ?
C9 C8 H8 120.1 . . ?
C7 C8 H8 120.1 . . ?
C8 C9 C10 122.2(9) . . ?
C8 C9 Cl1 116.9(9) . . ?
C10 C9 Cl1 120.9(9) . . ?
C9 C10 C15 118.7(9) . . ?
C9 C10 C11 122.9(10) . . ?
C15 C10 C11 118.3(10) . . ?
C12 C11 C10 120.5(11) . . ?
C12 C11 H11 119.7 . . ?
C10 C11 H11 119.7 . . ?
C11 C12 C13 120.5(10) . . ?
C11 C12 H12 119.7 . . ?
C13 C12 H12 119.7 . . ?
C14 C13 C12 121.2(11) . . ?
C14 C13 H13 119.4 . . ?
C12 C13 H13 119.4 . . ?
C13 C14 C15 121.1(11) . . ?
C13 C14 H14 119.4 . . ?
C15 C14 H14 119.4 . . ?
C14 C15 C6 123.3(9) . . ?
C14 C15 C10 118.3(9) . . ?
C6 C15 C10 118.4(9) . . ?
C4 N1 C1 116.5(8) . . ?
C2 N2 C3 116.9(9) . . ?
C2 N2 Hg1 122.6(7) . . ?
C3 N2 Hg1 120.4(6) . . ?
C5 N3 C6 129.9(8) . . ?
C5 N3 H3B 115.0 . . ?
C6 N3 H3B 115.0 . . ?
N2 Hg1 I1 98.1(2) . . ?
N2 Hg1 I2 99.00(19) . . ?
I1 Hg1 I2 161.91(4) . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
N1 C1 C2 N2 -0.4(19) . . . . ?
N2 C3 C4 N1 -0.4(16) . . . . ?
N2 C3 C4 C5 -179.6(9) . . . . ?
N1 C4 C5 O1 -170.2(10) . . . . ?
C3 C4 C5 O1 9.1(15) . . . . ?
N1 C4 C5 N3 9.1(13) . . . . ?
C3 C4 C5 N3 -171.7(9) . . . . ?
N3 C6 C7 C8 178.3(10) . . . . ?
C15 C6 C7 C8 -3.0(16) . . . . ?
C6 C7 C8 C9 1.2(16) . . . . ?
C7 C8 C9 C10 1.2(16) . . . . ?
C7 C8 C9 Cl1 -178.4(8) . . . . ?
C8 C9 C10 C15 -1.7(15) . . . . ?
Cl1 C9 C10 C15 177.8(7) . . . . ?
C8 C9 C10 C11 177.5(10) . . . . ?
Cl1 C9 C10 C11 -3.0(15) . . . . ?
C9 C10 C11 C12 -179.2(11) . . . . ?
C15 C10 C11 C12 0.0(16) . . . . ?
C10 C11 C12 C13 1.4(18) . . . . ?
C11 C12 C13 C14 -3(2) . . . . ?
C12 C13 C14 C15 3.1(19) . . . . ?
C13 C14 C15 C6 177.8(11) . . . . ?
C13 C14 C15 C10 -1.7(16) . . . . ?
C7 C6 C15 C14 -177.1(10) . . . . ?
N3 C6 C15 C14 1.7(15) . . . . ?
C7 C6 C15 C10 2.4(14) . . . . ?
N3 C6 C15 C10 -178.8(8) . . . . ?
C9 C10 C15 C14 179.4(10) . . . . ?
C11 C10 C15 C14 0.2(14) . . . . ?
C9 C10 C15 C6 -0.1(13) . . . . ?
C11 C10 C15 C6 -179.3(9) . . . . ?
C3 C4 N1 C1 -0.5(15) . . . . ?
C5 C4 N1 C1 178.7(10) . . . . ?
C2 C1 N1 C4 0.9(17) . . . . ?
C1 C2 N2 C3 -0.5(17) . . . . ?
C1 C2 N2 Hg1 176.8(9) . . . . ?
C4 C3 N2 C2 0.9(16) . . . . ?
C4 C3 N2 Hg1 -176.5(7) . . . . ?
O1 C5 N3 C6 -1.7(18) . . . . ?
C4 C5 N3 C6 179.1(9) . . . . ?
C7 C6 N3 C5 -10.6(17) . . . . ?
C15 C6 N3 C5 170.6(10) . . . . ?
C2 N2 Hg1 I1 -149.0(9) . . . . ?
C3 N2 Hg1 I1 28.2(9) . . . . ?
C2 N2 Hg1 I2 25.2(9) . . . . ?
C3 N2 Hg1 I2 -157.6(8) . . . . ?

_diffrn_measured_fraction_theta_max 0.987
_diffrn_reflns_theta_full        29.23
_diffrn_measured_fraction_theta_full 0.987
_refine_diff_density_max         1.200
_refine_diff_density_min         -1.180
_refine_diff_density_rms         0.425
####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_d:\determination\solution\kh488\kh488-2
_database_code_depnum_ccdc_archive 'CCDC 1016905'
_audit_update_record             
;
2014-07-29 deposited with the CCDC.
2016-05-24 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C15 H10 Br2 Cl1 Hg1 N3 O1'
_chemical_formula_weight         644.10

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Hg Hg -2.3894 9.2266 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Br Br -0.2901 2.4595 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_symmetry_cell_setting           Triclinic
_symmetry_space_group_name_H-M   P-1

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

_cell_length_a                   7.8587(9)
_cell_length_b                   9.8104(10)
_cell_length_c                   11.5257(13)
_cell_angle_alpha                76.986(8)
_cell_angle_beta                 80.953(9)
_cell_angle_gamma                75.314(9)
_cell_volume                     832.75(16)
_cell_formula_units_Z            2
_cell_measurement_temperature    298(2)
_cell_measurement_reflns_used    9109
_cell_measurement_theta_min      1.82
_cell_measurement_theta_max      29.20

_exptl_crystal_description       Block
_exptl_crystal_colour            Yellow
_exptl_crystal_size_max          0.15
_exptl_crystal_size_mid          0.12
_exptl_crystal_size_min          0.11
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    2.569
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             592
_exptl_absorpt_coefficient_mu    14.205
_exptl_absorpt_correction_type   numerical
_exptl_absorpt_correction_T_min  0.140
_exptl_absorpt_correction_T_max  0.212
_exptl_absorpt_process_details   'shape of crystal determined optically'

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      298(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'STOE IPDS II'
_diffrn_measurement_method       'rotation method'
_diffrn_detector_area_resol_mean '0.15 mm'
_diffrn_standards_number         0
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            9109
_diffrn_reflns_av_R_equivalents  0.0645
_diffrn_reflns_av_sigmaI/netI    0.0623
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_theta_min         1.82
_diffrn_reflns_theta_max         29.20
_reflns_number_total             4459
_reflns_number_gt                3293
_reflns_threshold_expression     >2sigma(I)

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

_refine_special_details          
; 
 Refinement of F² against ALL reflections.  The weighted R-factor wR and 
 goodness of fit S are based on F², conventional R-factors R are based 
 on F, with F set to zero for negative F². The threshold expression of 
 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is 
 not relevant to the choice of reflections for refinement.  R-factors based 
 on F² are statistically about twice as large as those based on F, and R- 
 factors based on ALL data will be even larger. 
;

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0463P)²+0.9574P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         4459
_refine_ls_number_parameters     208
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0756
_refine_ls_R_factor_gt           0.0479
_refine_ls_wR_factor_ref         0.1078
_refine_ls_wR_factor_gt          0.0975
_refine_ls_goodness_of_fit_ref   1.049
_refine_ls_restrained_S_all      1.049
_refine_ls_shift/su_max          0.008
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C 0.4687(11) 0.8920(8) 0.2881(7) 0.0465(18) Uani 1 1 d . . .
H1 H 0.5048 0.9752 0.2485 0.056 Uiso 1 1 calc R . .
C2 C 0.5209(11) 0.7696(8) 0.2387(7) 0.0465(17) Uani 1 1 d . . .
H2 H 0.5904 0.7739 0.1653 0.056 Uiso 1 1 calc R . .
C3 C 0.3772(10) 0.6479(8) 0.3951(6) 0.0408(16) Uani 1 1 d . . .
H3 H 0.3412 0.5645 0.4343 0.049 Uiso 1 1 calc R . .
C4 C 0.3262(9) 0.7667(7) 0.4467(6) 0.0362(14) Uani 1 1 d . . .
C5 C 0.2148(10) 0.7635(8) 0.5666(6) 0.0382(15) Uani 1 1 d . . .
C6 C 0.0535(10) 0.9384(8) 0.6966(6) 0.0383(14) Uani 1 1 d . . .
C7 C -0.0273(11) 0.8447(8) 0.7828(7) 0.0461(18) Uani 1 1 d . . .
H7 H -0.0142 0.7504 0.7743 0.055 Uiso 1 1 calc R . .
C8 C -0.1303(11) 0.8942(9) 0.8840(7) 0.0501(19) Uani 1 1 d . . .
H8 H -0.1842 0.8315 0.9422 0.060 Uiso 1 1 calc R . .
C9 C -0.1510(10) 1.0297(9) 0.8971(7) 0.0456(17) Uani 1 1 d . . .
C10 C -0.0686(10) 1.1310(8) 0.8125(6) 0.0402(16) Uani 1 1 d . . .
C11 C -0.0849(11) 1.2721(9) 0.8251(8) 0.0495(19) Uani 1 1 d . . .
H11 H -0.1506 1.3032 0.8925 0.059 Uiso 1 1 calc R . .
C12 C -0.0072(11) 1.3645(9) 0.7414(8) 0.0491(19) Uani 1 1 d . . .
H12 H -0.0175 1.4572 0.7528 0.059 Uiso 1 1 calc R . .
C13 C 0.0890(12) 1.3214(8) 0.6375(8) 0.0508(19) Uani 1 1 d . . .
H13 H 0.1382 1.3863 0.5785 0.061 Uiso 1 1 calc R . .
C14 C 0.1098(10) 1.1834(8) 0.6235(7) 0.0429(16) Uani 1 1 d . . .
H14 H 0.1765 1.1552 0.5552 0.052 Uiso 1 1 calc R . .
C15 C 0.0341(9) 1.0829(7) 0.7083(6) 0.0350(14) Uani 1 1 d . . .
N1 N 0.3668(9) 0.8907(6) 0.3924(5) 0.0424(14) Uani 1 1 d . . .
N2 N 0.4770(8) 0.6483(7) 0.2903(5) 0.0410(13) Uani 1 1 d . . .
N3 N 0.1540(9) 0.8968(6) 0.5929(5) 0.0424(14) Uani 1 1 d . . .
H3B H 0.1809 0.9658 0.5382 0.051 Uiso 1 1 calc R . .
O1 O 0.1905(8) 0.6501(6) 0.6302(5) 0.0499(13) Uani 1 1 d . . .
Hg1 Hg 0.55710(5) 0.43391(3) 0.18878(3) 0.04771(12) Uani 1 1 d . . .
Cl1 Cl -0.2897(3) 1.0879(3) 1.01973(19) 0.0616(6) Uani 1 1 d . . .
Br1 Br 0.38552(13) 0.27745(10) 0.32178(8) 0.0600(2) Uani 1 1 d . . .
Br2 Br 0.74271(13) 0.53834(10) 0.02144(8) 0.0603(2) Uani 1 1 d . . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
C1 N1 1.335(9) . ?
C1 C2 1.385(11) . ?
C1 H1 0.9300 . ?
C2 N2 1.309(9) . ?
C2 H2 0.9300 . ?
C3 N2 1.332(9) . ?
C3 C4 1.369(9) . ?
C3 H3 0.9300 . ?
C4 N1 1.328(9) . ?
C4 C5 1.514(9) . ?
C5 O1 1.228(9) . ?
C5 N3 1.359(9) . ?
C6 C7 1.386(10) . ?
C6 N3 1.407(8) . ?
C6 C15 1.421(9) . ?
C7 C8 1.418(10) . ?
C7 H7 0.9300 . ?
C8 C9 1.338(11) . ?
C8 H8 0.9300 . ?
C9 C10 1.432(10) . ?
C9 Cl1 1.754(7) . ?
C10 C11 1.395(10) . ?
C10 C15 1.440(9) . ?
C11 C12 1.351(12) . ?
C11 H11 0.9300 . ?
C12 C13 1.402(11) . ?
C12 H12 0.9300 . ?
C13 C14 1.364(10) . ?
C13 H13 0.9300 . ?
C14 C15 1.401(9) . ?
C14 H14 0.9300 . ?
N2 Hg1 2.528(6) . ?
N3 H3B 0.8600 . ?
Hg1 Br1 2.4215(9) . ?
Hg1 Br2 2.4249(9) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
N1 C1 C2 120.2(7) . . ?
N1 C1 H1 119.9 . . ?
C2 C1 H1 119.9 . . ?
N2 C2 C1 123.1(7) . . ?
N2 C2 H2 118.4 . . ?
C1 C2 H2 118.4 . . ?
N2 C3 C4 121.9(7) . . ?
N2 C3 H3 119.1 . . ?
C4 C3 H3 119.1 . . ?
N1 C4 C3 121.8(6) . . ?
N1 C4 C5 117.1(6) . . ?
C3 C4 C5 121.1(6) . . ?
O1 C5 N3 126.5(6) . . ?
O1 C5 C4 121.5(6) . . ?
N3 C5 C4 111.9(6) . . ?
C7 C6 N3 121.9(6) . . ?
C7 C6 C15 121.0(6) . . ?
N3 C6 C15 117.1(6) . . ?
C6 C7 C8 119.2(7) . . ?
C6 C7 H7 120.4 . . ?
C8 C7 H7 120.4 . . ?
C9 C8 C7 121.0(7) . . ?
C9 C8 H8 119.5 . . ?
C7 C8 H8 119.5 . . ?
C8 C9 C10 122.5(7) . . ?
C8 C9 Cl1 119.1(6) . . ?
C10 C9 Cl1 118.4(6) . . ?
C11 C10 C9 123.7(7) . . ?
C11 C10 C15 119.2(7) . . ?
C9 C10 C15 117.1(6) . . ?
C12 C11 C10 121.4(7) . . ?
C12 C11 H11 119.3 . . ?
C10 C11 H11 119.3 . . ?
C11 C12 C13 120.4(7) . . ?
C11 C12 H12 119.8 . . ?
C13 C12 H12 119.8 . . ?
C14 C13 C12 119.5(7) . . ?
C14 C13 H13 120.2 . . ?
C12 C13 H13 120.2 . . ?
C13 C14 C15 122.3(7) . . ?
C13 C14 H14 118.9 . . ?
C15 C14 H14 118.9 . . ?
C14 C15 C6 123.7(6) . . ?
C14 C15 C10 117.1(6) . . ?
C6 C15 C10 119.2(6) . . ?
C4 N1 C1 116.8(6) . . ?
C2 N2 C3 116.1(6) . . ?
C2 N2 Hg1 121.7(5) . . ?
C3 N2 Hg1 122.1(5) . . ?
C5 N3 C6 129.5(6) . . ?
C5 N3 H3B 115.3 . . ?
C6 N3 H3B 115.3 . . ?
Br1 Hg1 Br2 163.59(3) . . ?
Br1 Hg1 N2 100.72(13) . . ?
Br2 Hg1 N2 95.52(13) . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
N1 C1 C2 N2 -0.9(13) . . . . ?
N2 C3 C4 N1 3.1(12) . . . . ?
N2 C3 C4 C5 -179.2(7) . . . . ?
N1 C4 C5 O1 -170.3(7) . . . . ?
C3 C4 C5 O1 11.9(11) . . . . ?
N1 C4 C5 N3 8.0(10) . . . . ?
C3 C4 C5 N3 -169.8(7) . . . . ?
N3 C6 C7 C8 -178.6(7) . . . . ?
C15 C6 C7 C8 -0.2(12) . . . . ?
C6 C7 C8 C9 0.3(13) . . . . ?
C7 C8 C9 C10 -1.4(14) . . . . ?
C7 C8 C9 Cl1 176.4(7) . . . . ?
C8 C9 C10 C11 -178.6(9) . . . . ?
Cl1 C9 C10 C11 3.5(11) . . . . ?
C8 C9 C10 C15 2.3(12) . . . . ?
Cl1 C9 C10 C15 -175.6(6) . . . . ?
C9 C10 C11 C12 -178.7(8) . . . . ?
C15 C10 C11 C12 0.4(13) . . . . ?
C10 C11 C12 C13 1.6(13) . . . . ?
C11 C12 C13 C14 -2.6(14) . . . . ?
C12 C13 C14 C15 1.7(13) . . . . ?
C13 C14 C15 C6 -179.9(8) . . . . ?
C13 C14 C15 C10 0.2(12) . . . . ?
C7 C6 C15 C14 -178.9(8) . . . . ?
N3 C6 C15 C14 -0.4(11) . . . . ?
C7 C6 C15 C10 1.1(12) . . . . ?
N3 C6 C15 C10 179.6(7) . . . . ?
C11 C10 C15 C14 -1.2(11) . . . . ?
C9 C10 C15 C14 177.9(7) . . . . ?
C11 C10 C15 C6 178.8(7) . . . . ?
C9 C10 C15 C6 -2.1(11) . . . . ?
C3 C4 N1 C1 -3.9(12) . . . . ?
C5 C4 N1 C1 178.4(7) . . . . ?
C2 C1 N1 C4 2.8(12) . . . . ?
C1 C2 N2 C3 0.1(12) . . . . ?
C1 C2 N2 Hg1 175.4(6) . . . . ?
C4 C3 N2 C2 -1.1(12) . . . . ?
C4 C3 N2 Hg1 -176.4(5) . . . . ?
O1 C5 N3 C6 1.1(14) . . . . ?
C4 C5 N3 C6 -177.1(7) . . . . ?
C7 C6 N3 C5 -12.1(13) . . . . ?
C15 C6 N3 C5 169.5(7) . . . . ?
C2 N2 Hg1 Br1 -169.9(6) . . . . ?
C3 N2 Hg1 Br1 5.2(6) . . . . ?
C2 N2 Hg1 Br2 7.8(6) . . . . ?
C3 N2 Hg1 Br2 -177.1(6) . . . . ?

_diffrn_measured_fraction_theta_max 0.987
_diffrn_reflns_theta_full        29.20
_diffrn_measured_fraction_theta_full 0.987
_refine_diff_density_max         1.086
_refine_diff_density_min         -1.077
_refine_diff_density_rms         0.172
####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_d:\determination\solution\kh490\kh490
_database_code_depnum_ccdc_archive 'CCDC 1016906'
_audit_update_record             
;
2014-07-29 deposited with the CCDC.
2016-05-24 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C15 H10 Cl3 Hg1 N3 O1'
_chemical_formula_weight         555.20

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

_symmetry_cell_setting           Triclinic
_symmetry_space_group_name_H-M   P-1

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

_cell_length_a                   7.7489(11)
_cell_length_b                   9.6446(12)
_cell_length_c                   11.3533(13)
_cell_angle_alpha                77.812(9)
_cell_angle_beta                 81.537(10)
_cell_angle_gamma                76.841(10)
_cell_volume                     803.20(18)
_cell_formula_units_Z            2
_cell_measurement_temperature    298(2)
_cell_measurement_reflns_used    8935
_cell_measurement_theta_min      2.21
_cell_measurement_theta_max      29.15

_exptl_crystal_description       Block
_exptl_crystal_colour            Yellow
_exptl_crystal_size_max          0.20
_exptl_crystal_size_mid          0.11
_exptl_crystal_size_min          0.10
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    2.296
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             520
_exptl_absorpt_coefficient_mu    10.086
_exptl_absorpt_correction_type   numerical
_exptl_absorpt_correction_T_min  0.915
_exptl_absorpt_correction_T_max  0.956
_exptl_absorpt_process_details   'shape of crystal determined optically'

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      298(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'STOE IPDS II'
_diffrn_measurement_method       'rotation method'
_diffrn_detector_area_resol_mean '0.15 mm'
_diffrn_standards_number         0
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            8935
_diffrn_reflns_av_R_equivalents  0.0825
_diffrn_reflns_av_sigmaI/netI    0.0641
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_theta_min         2.21
_diffrn_reflns_theta_max         29.15
_reflns_number_total             4306
_reflns_number_gt                3520
_reflns_threshold_expression     >2sigma(I)

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

_refine_special_details          
; 
 Refinement of F² against ALL reflections.  The weighted R-factor wR and 
 goodness of fit S are based on F², conventional R-factors R are based 
 on F, with F set to zero for negative F². The threshold expression of 
 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is 
 not relevant to the choice of reflections for refinement.  R-factors based 
 on F² are statistically about twice as large as those based on F, and R- 
 factors based on ALL data will be even larger. 
;

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0638P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         4306
_refine_ls_number_parameters     208
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0625
_refine_ls_R_factor_gt           0.0481
_refine_ls_wR_factor_ref         0.1183
_refine_ls_wR_factor_gt          0.1119
_refine_ls_goodness_of_fit_ref   1.085
_refine_ls_restrained_S_all      1.085
_refine_ls_shift/su_max          0.007
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C 0.4772(10) 0.8971(7) 0.2851(7) 0.0430(15) Uani 1 1 d . . .
H1 H 0.5112 0.9826 0.2445 0.052 Uiso 1 1 calc R . .
C2 C 0.5322(9) 0.7737(7) 0.2339(6) 0.0399(14) Uani 1 1 d . . .
H2 H 0.6045 0.7780 0.1607 0.048 Uiso 1 1 calc R . .
C3 C 0.3851(9) 0.6459(6) 0.3939(6) 0.0344(12) Uani 1 1 d . . .
H3 H 0.3514 0.5597 0.4330 0.041 Uiso 1 1 calc R . .
C4 C 0.3317(9) 0.7675(6) 0.4475(5) 0.0324(12) Uani 1 1 d . . .
C5 C 0.2219(9) 0.7651(6) 0.5664(6) 0.0352(12) Uani 1 1 d . . .
C6 C 0.0539(9) 0.9402(6) 0.6956(5) 0.0329(12) Uani 1 1 d . . .
C7 C -0.0289(11) 0.8454(7) 0.7816(7) 0.0436(15) Uani 1 1 d . . .
H7 H -0.0155 0.7497 0.7727 0.052 Uiso 1 1 calc R . .
C8 C -0.1340(10) 0.8944(7) 0.8831(6) 0.0427(15) Uani 1 1 d . . .
H8 H -0.1905 0.8309 0.9409 0.051 Uiso 1 1 calc R . .
C9 C -0.1532(10) 1.0337(8) 0.8970(6) 0.0391(14) Uani 1 1 d . . .
C10 C -0.0701(8) 1.1354(7) 0.8116(6) 0.0337(12) Uani 1 1 d . . .
C11 C -0.0857(11) 1.2796(8) 0.8265(7) 0.0446(15) Uani 1 1 d . . .
H11 H -0.1483 1.3092 0.8964 0.054 Uiso 1 1 calc R . .
C12 C -0.0106(10) 1.3763(7) 0.7404(7) 0.0453(16) Uani 1 1 d . . .
H12 H -0.0226 1.4709 0.7517 0.054 Uiso 1 1 calc R . .
C13 C 0.0853(10) 1.3330(7) 0.6342(7) 0.0438(15) Uani 1 1 d . . .
H13 H 0.1332 1.3996 0.5741 0.053 Uiso 1 1 calc R . .
C14 C 0.1073(9) 1.1923(7) 0.6201(6) 0.0365(13) Uani 1 1 d . . .
H14 H 0.1732 1.1644 0.5505 0.044 Uiso 1 1 calc R . .
C15 C 0.0332(8) 1.0877(6) 0.7077(5) 0.0298(11) Uani 1 1 d . . .
N1 N 0.3765(8) 0.8960(6) 0.3915(5) 0.0382(12) Uani 1 1 d . . .
N2 N 0.4848(8) 0.6508(6) 0.2862(5) 0.0373(11) Uani 1 1 d . . .
N3 N 0.1587(8) 0.8985(6) 0.5919(5) 0.0363(11) Uani 1 1 d . . .
H3B H 0.1864 0.9684 0.5368 0.044 Uiso 1 1 calc R . .
Cl1 Cl 0.3936(3) 0.2840(2) 0.3142(2) 0.0582(5) Uani 1 1 d . . .
Cl2 Cl 0.7329(3) 0.5397(2) 0.02239(19) 0.0603(5) Uani 1 1 d . . .
Cl3 Cl -0.2917(3) 1.0903(2) 1.02094(16) 0.0540(5) Uani 1 1 d . . .
Hg1 Hg 0.55877(4) 0.43272(3) 0.18319(2) 0.04451(11) Uani 1 1 d . . .
O1 O 0.1984(8) 0.6504(5) 0.6303(5) 0.0465(12) Uani 1 1 d . . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
C1 N1 1.337(9) . ?
C1 C2 1.387(10) . ?
C1 H1 0.9300 . ?
C2 N2 1.315(9) . ?
C2 H2 0.9300 . ?
C3 N2 1.345(8) . ?
C3 C4 1.388(8) . ?
C3 H3 0.9300 . ?
C4 N1 1.363(8) . ?
C4 C5 1.485(9) . ?
C5 O1 1.223(8) . ?
C5 N3 1.345(8) . ?
C6 C7 1.381(9) . ?
C6 N3 1.406(7) . ?
C6 C15 1.428(8) . ?
C7 C8 1.413(9) . ?
C7 H7 0.9300 . ?
C8 C9 1.358(10) . ?
C8 H8 0.9300 . ?
C9 C10 1.421(10) . ?
C9 Cl3 1.744(7) . ?
C10 C11 1.413(9) . ?
C10 C15 1.424(8) . ?
C11 C12 1.364(11) . ?
C11 H11 0.9300 . ?
C12 C13 1.410(11) . ?
C12 H12 0.9300 . ?
C13 C14 1.369(9) . ?
C13 H13 0.9300 . ?
C14 C15 1.418(9) . ?
C14 H14 0.9300 . ?
N2 Hg1 2.532(5) . ?
N3 H3B 0.8600 . ?
Cl1 Hg1 2.299(2) . ?
Cl2 Hg1 2.309(2) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
N1 C1 C2 121.6(6) . . ?
N1 C1 H1 119.2 . . ?
C2 C1 H1 119.2 . . ?
N2 C2 C1 121.7(6) . . ?
N2 C2 H2 119.1 . . ?
C1 C2 H2 119.1 . . ?
N2 C3 C4 120.9(5) . . ?
N2 C3 H3 119.5 . . ?
C4 C3 H3 119.5 . . ?
N1 C4 C3 120.9(6) . . ?
N1 C4 C5 117.1(5) . . ?
C3 C4 C5 122.1(6) . . ?
O1 C5 N3 126.8(6) . . ?
O1 C5 C4 120.8(6) . . ?
N3 C5 C4 112.4(5) . . ?
C7 C6 N3 122.4(6) . . ?
C7 C6 C15 120.7(5) . . ?
N3 C6 C15 116.8(5) . . ?
C6 C7 C8 119.7(6) . . ?
C6 C7 H7 120.2 . . ?
C8 C7 H7 120.2 . . ?
C9 C8 C7 120.4(6) . . ?
C9 C8 H8 119.8 . . ?
C7 C8 H8 119.8 . . ?
C8 C9 C10 122.1(6) . . ?
C8 C9 Cl3 118.5(5) . . ?
C10 C9 Cl3 119.3(5) . . ?
C11 C10 C9 122.6(6) . . ?
C11 C10 C15 119.6(6) . . ?
C9 C10 C15 117.8(6) . . ?
C12 C11 C10 121.2(6) . . ?
C12 C11 H11 119.4 . . ?
C10 C11 H11 119.4 . . ?
C11 C12 C13 120.1(6) . . ?
C11 C12 H12 120.0 . . ?
C13 C12 H12 120.0 . . ?
C14 C13 C12 119.6(6) . . ?
C14 C13 H13 120.2 . . ?
C12 C13 H13 120.2 . . ?
C13 C14 C15 122.3(6) . . ?
C13 C14 H14 118.8 . . ?
C15 C14 H14 118.8 . . ?
C14 C15 C10 117.1(5) . . ?
C14 C15 C6 123.6(5) . . ?
C10 C15 C6 119.2(5) . . ?
C1 N1 C4 116.8(5) . . ?
C2 N2 C3 118.1(5) . . ?
C2 N2 Hg1 121.8(4) . . ?
C3 N2 Hg1 120.0(4) . . ?
C5 N3 C6 129.3(5) . . ?
C5 N3 H3B 115.4 . . ?
C6 N3 H3B 115.4 . . ?
Cl1 Hg1 Cl2 165.90(8) . . ?
Cl1 Hg1 N2 99.99(14) . . ?
Cl2 Hg1 N2 93.90(14) . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
N1 C1 C2 N2 1.5(12) . . . . ?
N2 C3 C4 N1 1.1(10) . . . . ?
N2 C3 C4 C5 -179.9(6) . . . . ?
N1 C4 C5 O1 -169.2(7) . . . . ?
C3 C4 C5 O1 11.8(11) . . . . ?
N1 C4 C5 N3 10.1(9) . . . . ?
C3 C4 C5 N3 -169.0(6) . . . . ?
N3 C6 C7 C8 -179.3(7) . . . . ?
C15 C6 C7 C8 -0.5(11) . . . . ?
C6 C7 C8 C9 -0.4(12) . . . . ?
C7 C8 C9 C10 0.1(12) . . . . ?
C7 C8 C9 Cl3 177.5(6) . . . . ?
C8 C9 C10 C11 -178.5(7) . . . . ?
Cl3 C9 C10 C11 4.1(10) . . . . ?
C8 C9 C10 C15 1.2(11) . . . . ?
Cl3 C9 C10 C15 -176.2(5) . . . . ?
C9 C10 C11 C12 -177.2(7) . . . . ?
C15 C10 C11 C12 3.2(11) . . . . ?
C10 C11 C12 C13 -0.2(12) . . . . ?
C11 C12 C13 C14 -2.2(12) . . . . ?
C12 C13 C14 C15 1.5(11) . . . . ?
C13 C14 C15 C10 1.4(10) . . . . ?
C13 C14 C15 C6 -180.0(7) . . . . ?
C11 C10 C15 C14 -3.7(10) . . . . ?
C9 C10 C15 C14 176.7(6) . . . . ?
C11 C10 C15 C6 177.6(6) . . . . ?
C9 C10 C15 C6 -2.0(9) . . . . ?
C7 C6 C15 C14 -176.9(7) . . . . ?
N3 C6 C15 C14 2.0(10) . . . . ?
C7 C6 C15 C10 1.7(10) . . . . ?
N3 C6 C15 C10 -179.4(6) . . . . ?
C2 C1 N1 C4 0.5(11) . . . . ?
C3 C4 N1 C1 -1.7(10) . . . . ?
C5 C4 N1 C1 179.2(6) . . . . ?
C1 C2 N2 C3 -2.1(11) . . . . ?
C1 C2 N2 Hg1 173.7(6) . . . . ?
C4 C3 N2 C2 0.9(10) . . . . ?
C4 C3 N2 Hg1 -175.1(5) . . . . ?
O1 C5 N3 C6 0.7(13) . . . . ?
C4 C5 N3 C6 -178.6(6) . . . . ?
C7 C6 N3 C5 -12.2(12) . . . . ?
C15 C6 N3 C5 168.9(7) . . . . ?
C2 N2 Hg1 Cl1 -170.8(5) . . . . ?
C3 N2 Hg1 Cl1 5.0(5) . . . . ?
C2 N2 Hg1 Cl2 6.8(6) . . . . ?
C3 N2 Hg1 Cl2 -177.5(5) . . . . ?

_diffrn_measured_fraction_theta_max 0.991
_diffrn_reflns_theta_full        29.15
_diffrn_measured_fraction_theta_full 0.991
_refine_diff_density_max         1.360
_refine_diff_density_min         -1.420
_refine_diff_density_rms         0.221
