# Electronic Supplementary Material (ESI) for CrystEngComm.
# This journal is © The Royal Society of Chemistry 2023

####################################################################### 
# 
# 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\754\kh754-abs1
_audit_block_doi                 10.5517/cc1290lz
_database_code_depnum_ccdc_archive 'CCDC 991770'
loop_
_citation_id
_citation_doi
_citation_year
1 10.1039/C4CE00692E 2014
_audit_update_record             
;
2014-03-14 deposited with the CCDC.	2024-01-03 downloaded from the CCDC.
;

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

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Br Br -0.2901 2.4595 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Hg Hg -2.3894 9.2266 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
I I -0.4742 1.8119 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_symmetry_cell_setting           Monoclinic
_symmetry_space_group_name_H-M   C2/c

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

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

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

_exptl_special_details           
; 
 ? 
;

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

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

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

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

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

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

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

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

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

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

_diffrn_measured_fraction_theta_max 1.000
_diffrn_reflns_theta_full        26.00
_diffrn_measured_fraction_theta_full 1.000
_refine_diff_density_max         1.614
_refine_diff_density_min         -1.248
_refine_diff_density_rms         0.347
####################################################################### 
# 
# 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\801\kh801
_database_code_depnum_ccdc_archive 'CCDC 1016668'
_audit_update_record             
;
2014-07-28 deposited with the CCDC.	2024-01-03 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C24 H18 Br2 Cl2 Hg1 N4 O2'
_chemical_formula_weight         825.71

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'
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'
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   C2/c

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

_cell_length_a                   22.680(2)
_cell_length_b                   4.9699(3)
_cell_length_c                   27.573(3)
_cell_angle_alpha                90.00
_cell_angle_beta                 123.819(7)
_cell_angle_gamma                90.00
_cell_volume                     2582.1(4)
_cell_formula_units_Z            4
_cell_measurement_temperature    298(2)
_cell_measurement_reflns_used    2817
_cell_measurement_theta_min      1.78
_cell_measurement_theta_max      27.00

_exptl_crystal_description       Prism
_exptl_crystal_colour            Colorless
_exptl_crystal_size_max          0.28
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.14
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    2.124
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1560
_exptl_absorpt_coefficient_mu    9.293
_exptl_absorpt_correction_type   numerical
_exptl_absorpt_correction_T_min  0.2150
_exptl_absorpt_correction_T_max  0.2981
_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            7779
_diffrn_reflns_av_R_equivalents  0.0895
_diffrn_reflns_av_sigmaI/netI    0.1002
_diffrn_reflns_limit_h_min       -28
_diffrn_reflns_limit_h_max       28
_diffrn_reflns_limit_k_min       -6
_diffrn_reflns_limit_k_max       6
_diffrn_reflns_limit_l_min       -34
_diffrn_reflns_limit_l_max       35
_diffrn_reflns_theta_min         1.78
_diffrn_reflns_theta_max         27.00
_reflns_number_total             2817
_reflns_number_gt                2162
_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)+(0.0966P)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         2817
_refine_ls_number_parameters     159
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0956
_refine_ls_R_factor_gt           0.0763
_refine_ls_wR_factor_ref         0.1248
_refine_ls_wR_factor_gt          0.1102
_refine_ls_goodness_of_fit_ref   1.004
_refine_ls_restrained_S_all      1.004
_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 -0.0958(7) 0.422(2) 0.1310(5) 0.045(3) Uani 1 1 d . . .
H1 H -0.0693 0.3222 0.1210 0.054 Uiso 1 1 calc R . .
C2 C -0.1341(8) 0.488(3) 0.1920(6) 0.052(3) Uani 1 1 d . . .
H2 H -0.1327 0.4432 0.2254 0.063 Uiso 1 1 calc R . .
C3 C -0.1806(9) 0.681(3) 0.1561(7) 0.061(4) Uani 1 1 d . . .
H3 H -0.2110 0.7626 0.1643 0.073 Uiso 1 1 calc R . .
C4 C -0.1818(7) 0.757(3) 0.1062(6) 0.050(3) Uani 1 1 d . . .
H4 H -0.2112 0.8937 0.0816 0.060 Uiso 1 1 calc R . .
C5 C -0.1375(6) 0.618(2) 0.0951(5) 0.040(2) Uani 1 1 d . . .
C6 C -0.1375(7) 0.698(2) 0.0425(5) 0.044(3) Uani 1 1 d . . .
C7 C -0.1203(8) 0.532(2) -0.0325(6) 0.046(3) Uani 1 1 d . . .
C8 C -0.1605(7) 0.370(2) -0.0820(5) 0.043(3) Uani 1 1 d . . .
H8 H -0.1925 0.2451 -0.0842 0.051 Uiso 1 1 calc R . .
C9 C -0.1516(8) 0.398(3) -0.1268(6) 0.049(3) Uani 1 1 d . . .
C10 C -0.1069(10) 0.579(3) -0.1270(8) 0.062(4) Uani 1 1 d . . .
H10 H -0.1029 0.5929 -0.1587 0.075 Uiso 1 1 calc R . .
C11 C -0.0679(11) 0.740(4) -0.0788(8) 0.081(5) Uani 1 1 d . . .
H11 H -0.0363 0.8635 -0.0776 0.097 Uiso 1 1 calc R . .
C12 C -0.0747(9) 0.720(3) -0.0306(7) 0.063(4) Uani 1 1 d . . .
H12 H -0.0488 0.8329 0.0015 0.076 Uiso 1 1 calc R . .
N1 N -0.0902(6) 0.360(2) 0.1814(4) 0.046(2) Uani 1 1 d . . .
N2 N -0.1282(7) 0.4994(18) 0.0144(5) 0.048(2) Uani 1 1 d . . .
H2B H -0.1270 0.3377 0.0260 0.057 Uiso 1 1 calc R . .
O1 O -0.1468(7) 0.9308(18) 0.0253(5) 0.063(3) Uani 1 1 d . . .
Hg1 Hg 0.0000 0.03185(13) 0.2500 0.0415(3) Uani 1 2 d S . .
Br1 Br -0.20753(8) 0.1842(4) -0.19515(6) 0.0658(5) Uani 1 1 d . . .
Cl1 Cl 0.0402(2) -0.0707(8) 0.19006(15) 0.0577(8) Uani 1 1 d . . .

loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_23
_atom_site_aniso_U_13
_atom_site_aniso_U_12
C1 0.053(7) 0.044(6) 0.041(6) -0.008(5) 0.028(6) -0.003(5)
C2 0.055(8) 0.059(8) 0.044(6) 0.003(6) 0.028(6) 0.006(6)
C3 0.064(9) 0.065(9) 0.059(8) -0.007(7) 0.037(8) 0.009(7)
C4 0.042(7) 0.042(6) 0.045(6) 0.008(6) 0.011(5) 0.003(6)
C5 0.037(6) 0.032(5) 0.036(5) -0.004(4) 0.011(5) -0.003(5)
C6 0.052(7) 0.025(5) 0.040(6) -0.001(4) 0.016(5) -0.005(5)
C7 0.058(8) 0.035(5) 0.045(6) 0.006(5) 0.030(6) 0.005(5)
C8 0.050(7) 0.038(5) 0.045(6) 0.006(5) 0.030(6) 0.004(5)
C9 0.053(8) 0.046(6) 0.049(7) 0.000(5) 0.028(6) 0.004(6)
C10 0.077(11) 0.053(8) 0.070(9) 0.015(7) 0.049(9) 0.001(7)
C11 0.109(15) 0.064(9) 0.089(12) -0.002(10) 0.067(12) -0.030(10)
C12 0.080(11) 0.050(7) 0.058(8) -0.009(6) 0.038(8) -0.022(7)
N1 0.049(6) 0.041(5) 0.040(5) 0.006(4) 0.021(5) -0.002(5)
N2 0.070(7) 0.025(4) 0.044(5) 0.010(4) 0.030(5) 0.006(4)
O1 0.104(9) 0.029(4) 0.058(6) 0.005(4) 0.046(6) 0.003(5)
Hg1 0.0411(4) 0.0483(4) 0.0326(3) 0.000 0.0189(3) 0.000
Br1 0.0629(9) 0.0888(11) 0.0442(7) -0.0061(7) 0.0287(7) -0.0022(8)
Cl1 0.066(2) 0.066(2) 0.0516(17) 0.0036(15) 0.0388(17) 0.0076(16)

_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 C5 1.334(19) . ?
C1 N1 1.357(15) . ?
C1 H1 0.9300 . ?
C2 N1 1.345(18) . ?
C2 C3 1.36(2) . ?
C2 H2 0.9300 . ?
C3 C4 1.411(19) . ?
C3 H3 0.9300 . ?
C4 C5 1.387(18) . ?
C4 H4 0.9300 . ?
C5 C6 1.506(17) . ?
C6 O1 1.221(15) . ?
C6 N2 1.343(15) . ?
C7 C12 1.372(19) . ?
C7 C8 1.399(19) . ?
C7 N2 1.411(16) . ?
C8 C9 1.367(17) . ?
C8 H8 0.9300 . ?
C9 C10 1.35(2) . ?
C9 Br1 1.905(14) . ?
C10 C11 1.37(2) . ?
C10 H10 0.9300 . ?
C11 C12 1.42(2) . ?
C11 H11 0.9300 . ?
C12 H12 0.9300 . ?
N1 Hg1 2.474(11) . ?
N2 H2B 0.8600 . ?
Hg1 Cl1 2.345(3) . ?
Hg1 Cl1 2.345(3) 2 ?
Hg1 N1 2.474(11) 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
C5 C1 N1 123.2(11) . . ?
C5 C1 H1 118.4 . . ?
N1 C1 H1 118.4 . . ?
N1 C2 C3 122.9(12) . . ?
N1 C2 H2 118.5 . . ?
C3 C2 H2 118.5 . . ?
C2 C3 C4 118.9(12) . . ?
C2 C3 H3 120.5 . . ?
C4 C3 H3 120.5 . . ?
C5 C4 C3 117.3(12) . . ?
C5 C4 H4 121.3 . . ?
C3 C4 H4 121.3 . . ?
C1 C5 C4 120.1(11) . . ?
C1 C5 C6 122.0(11) . . ?
C4 C5 C6 117.9(11) . . ?
O1 C6 N2 121.5(11) . . ?
O1 C6 C5 122.2(11) . . ?
N2 C6 C5 116.3(9) . . ?
C12 C7 C8 119.9(12) . . ?
C12 C7 N2 121.4(12) . . ?
C8 C7 N2 118.7(11) . . ?
C9 C8 C7 118.5(12) . . ?
C9 C8 H8 120.7 . . ?
C7 C8 H8 120.7 . . ?
C10 C9 C8 123.9(14) . . ?
C10 C9 Br1 117.0(11) . . ?
C8 C9 Br1 119.0(10) . . ?
C9 C10 C11 117.7(14) . . ?
C9 C10 H10 121.1 . . ?
C11 C10 H10 121.1 . . ?
C10 C11 C12 121.1(14) . . ?
C10 C11 H11 119.4 . . ?
C12 C11 H11 119.4 . . ?
C7 C12 C11 118.8(14) . . ?
C7 C12 H12 120.6 . . ?
C11 C12 H12 120.6 . . ?
C2 N1 C1 117.2(11) . . ?
C2 N1 Hg1 122.9(8) . . ?
C1 N1 Hg1 119.9(8) . . ?
C6 N2 C7 125.7(9) . . ?
C6 N2 H2B 117.1 . . ?
C7 N2 H2B 117.1 . . ?
Cl1 Hg1 Cl1 154.89(19) . 2 ?
Cl1 Hg1 N1 101.6(3) . 2 ?
Cl1 Hg1 N1 94.9(3) 2 2 ?
Cl1 Hg1 N1 94.9(3) . . ?
Cl1 Hg1 N1 101.6(3) 2 . ?
N1 Hg1 N1 97.5(5) 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 C2 C3 C4 -2(2) . . . . ?
C2 C3 C4 C5 3(2) . . . . ?
N1 C1 C5 C4 -5(2) . . . . ?
N1 C1 C5 C6 174.2(11) . . . . ?
C3 C4 C5 C1 0.0(19) . . . . ?
C3 C4 C5 C6 -179.1(12) . . . . ?
C1 C5 C6 O1 -145.9(15) . . . . ?
C4 C5 C6 O1 33.3(19) . . . . ?
C1 C5 C6 N2 35.5(18) . . . . ?
C4 C5 C6 N2 -145.3(13) . . . . ?
C12 C7 C8 C9 2(2) . . . . ?
N2 C7 C8 C9 -178.6(12) . . . . ?
C7 C8 C9 C10 -1(2) . . . . ?
C7 C8 C9 Br1 -178.5(10) . . . . ?
C8 C9 C10 C11 1(3) . . . . ?
Br1 C9 C10 C11 178.1(14) . . . . ?
C9 C10 C11 C12 -1(3) . . . . ?
C8 C7 C12 C11 -2(2) . . . . ?
N2 C7 C12 C11 178.5(15) . . . . ?
C10 C11 C12 C7 1(3) . . . . ?
C3 C2 N1 C1 -3(2) . . . . ?
C3 C2 N1 Hg1 175.6(12) . . . . ?
C5 C1 N1 C2 6(2) . . . . ?
C5 C1 N1 Hg1 -172.3(10) . . . . ?
O1 C6 N2 C7 7(2) . . . . ?
C5 C6 N2 C7 -174.2(12) . . . . ?
C12 C7 N2 C6 47(2) . . . . ?
C8 C7 N2 C6 -132.5(14) . . . . ?
C2 N1 Hg1 Cl1 178.1(11) . . . . ?
C1 N1 Hg1 Cl1 -3.3(9) . . . . ?
C2 N1 Hg1 Cl1 17.1(11) . . . 2 ?
C1 N1 Hg1 Cl1 -164.3(9) . . . 2 ?
C2 N1 Hg1 N1 -79.4(11) . . . 2 ?
C1 N1 Hg1 N1 99.1(10) . . . 2 ?

_diffrn_measured_fraction_theta_max 0.997
_diffrn_reflns_theta_full        27.00
_diffrn_measured_fraction_theta_full 0.997
_refine_diff_density_max         1.250
_refine_diff_density_min         -1.251
_refine_diff_density_rms         0.346
####################################################################### 
# 
# 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\897\kh897
_database_code_depnum_ccdc_archive 'CCDC 1016672'
_audit_update_record             
;
2014-07-28 deposited with the CCDC.	2024-01-03 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C24 H18 Hg3 I8 N4 O2'
_chemical_formula_weight         2011.39

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'

_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                   4.5421(3)
_cell_length_b                   21.7134(19)
_cell_length_c                   19.3708(13)
_cell_angle_alpha                90.00
_cell_angle_beta                 92.541(6)
_cell_angle_gamma                90.00
_cell_volume                     1908.6(2)
_cell_formula_units_Z            2
_cell_measurement_temperature    298(2)
_cell_measurement_reflns_used    21386
_cell_measurement_theta_min      1.88
_cell_measurement_theta_max      29.28

_exptl_crystal_description       Needle
_exptl_crystal_colour            Colorless
_exptl_crystal_size_max          0.24
_exptl_crystal_size_mid          0.10
_exptl_crystal_size_min          0.06
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    3.500
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1740
_exptl_absorpt_coefficient_mu    18.534
_exptl_absorpt_correction_type   numerical
_exptl_absorpt_correction_T_min  0.1245
_exptl_absorpt_correction_T_max  0.4005
_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            21386
_diffrn_reflns_av_R_equivalents  0.0998
_diffrn_reflns_av_sigmaI/netI    0.0845
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_k_min       -29
_diffrn_reflns_limit_k_max       29
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_limit_l_max       26
_diffrn_reflns_theta_min         1.88
_diffrn_reflns_theta_max         29.28
_reflns_number_total             5146
_reflns_number_gt                4518
_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)+(0.0140P)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         5146
_refine_ls_number_parameters     187
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0815
_refine_ls_R_factor_gt           0.0640
_refine_ls_wR_factor_ref         0.1276
_refine_ls_wR_factor_gt          0.1055
_refine_ls_goodness_of_fit_ref   0.912
_refine_ls_restrained_S_all      0.912
_refine_ls_shift/su_max          0.003
_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 0.554(3) 0.1538(6) 0.6767(7) 0.036(3) Uani 1 1 d . . .
H1 H 0.6810 0.1209 0.6860 0.044 Uiso 1 1 calc R . .
C2 C 0.276(4) 0.2327(7) 0.7170(8) 0.050(4) Uani 1 1 d . . .
H2 H 0.2021 0.2546 0.7537 0.059 Uiso 1 1 calc R . .
C3 C 0.196(3) 0.2489(7) 0.6495(8) 0.045(4) Uani 1 1 d . . .
H3 H 0.0750 0.2830 0.6413 0.054 Uiso 1 1 calc R . .
C4 C 0.290(3) 0.2158(6) 0.5952(8) 0.042(4) Uani 1 1 d . . .
H4 H 0.2317 0.2261 0.5501 0.050 Uiso 1 1 calc R . .
C5 C 0.471(3) 0.1675(6) 0.6085(7) 0.034(3) Uani 1 1 d . . .
C6 C 0.597(3) 0.1279(6) 0.5543(7) 0.034(3) Uani 1 1 d . . .
C7 C 0.481(3) 0.0868(6) 0.4363(7) 0.031(3) Uani 1 1 d . . .
C8 C 0.341(3) 0.1064(6) 0.3758(8) 0.035(3) Uani 1 1 d . . .
H8 H 0.2097 0.1391 0.3767 0.042 Uiso 1 1 calc R . .
C9 C 0.394(3) 0.0784(6) 0.3143(7) 0.035(3) Uani 1 1 d . . .
C10 C 0.583(3) 0.0297(6) 0.3118(8) 0.041(4) Uani 1 1 d . . .
H10 H 0.6215 0.0114 0.2698 0.049 Uiso 1 1 calc R . .
C11 C 0.715(3) 0.0084(6) 0.3718(8) 0.041(3) Uani 1 1 d . . .
H11 H 0.8352 -0.0263 0.3706 0.049 Uiso 1 1 calc R . .
C12 C 0.674(3) 0.0376(6) 0.4349(8) 0.039(3) Uani 1 1 d . . .
H12 H 0.7734 0.0242 0.4751 0.047 Uiso 1 1 calc R . .
N1 N 0.457(3) 0.1867(5) 0.7292(6) 0.045(3) Uani 1 1 d . . .
N2 N 0.414(2) 0.1167(5) 0.4976(6) 0.034(3) Uani 1 1 d . . .
H2A H 0.2354 0.1296 0.5001 0.041 Uiso 1 1 calc R . .
O1 O 0.856(2) 0.1095(5) 0.5587(5) 0.050(3) Uani 1 1 d . . .
Hg1 Hg 0.57401(15) 0.15856(3) 0.85267(4) 0.05120(19) Uani 1 1 d . . .
Hg2 Hg 1.0000 0.0000 1.0000 0.0744(3) Uani 1 2 d S . .
I1 I 0.1760(3) 0.11242(5) 0.22352(6) 0.0520(3) Uani 1 1 d . . .
I2 I 0.9555(2) 0.06941(4) 0.83246(5) 0.0446(3) Uani 1 1 d . . .
I3 I 0.2785(2) 0.24246(5) 0.91785(6) 0.0510(3) Uani 1 1 d . . .
I4 I 0.6627(3) 0.08641(6) 1.04369(7) 0.0678(4) Uani 1 1 d . . .

loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_23
_atom_site_aniso_U_13
_atom_site_aniso_U_12
C1 0.046(8) 0.033(6) 0.030(7) 0.008(6) 0.000(7) 0.007(6)
C2 0.063(11) 0.051(8) 0.034(9) -0.011(7) -0.009(8) 0.014(8)
C3 0.043(9) 0.045(8) 0.045(10) -0.009(7) -0.022(7) 0.002(7)
C4 0.057(10) 0.033(7) 0.034(8) 0.001(6) -0.008(7) 0.007(7)
C5 0.035(7) 0.032(7) 0.034(8) -0.001(6) 0.000(6) -0.016(6)
C6 0.028(7) 0.039(7) 0.037(8) 0.000(6) 0.004(6) -0.005(6)
C7 0.015(6) 0.040(7) 0.039(8) -0.001(6) 0.006(6) -0.005(5)
C8 0.017(6) 0.028(6) 0.059(10) -0.002(6) 0.002(6) -0.007(5)
C9 0.032(7) 0.041(7) 0.033(7) 0.001(6) 0.001(6) -0.010(6)
C10 0.039(8) 0.032(7) 0.053(10) -0.012(7) 0.012(7) 0.009(6)
C11 0.038(8) 0.042(7) 0.043(9) 0.008(7) 0.015(7) 0.016(7)
C12 0.043(9) 0.032(7) 0.044(9) 0.012(6) 0.010(7) -0.004(6)
N1 0.056(8) 0.035(6) 0.044(8) 0.000(5) 0.000(6) 0.007(6)
N2 0.029(6) 0.034(6) 0.039(7) 0.002(5) -0.008(5) 0.007(5)
O1 0.019(5) 0.073(7) 0.057(7) -0.014(6) -0.005(5) 0.006(5)
Hg1 0.0585(4) 0.0464(3) 0.0491(4) -0.0040(3) 0.0066(3) 0.0180(3)
Hg2 0.0731(7) 0.0748(7) 0.0763(8) -0.0075(6) 0.0142(6) 0.0320(6)
I1 0.0612(7) 0.0559(6) 0.0386(6) 0.0065(5) -0.0017(5) -0.0015(5)
I2 0.0458(6) 0.0385(5) 0.0494(6) -0.0053(4) 0.0005(5) 0.0076(4)
I3 0.0465(6) 0.0481(5) 0.0585(7) -0.0174(5) 0.0040(5) 0.0066(5)
I4 0.0677(8) 0.0709(7) 0.0648(8) -0.0147(6) 0.0025(6) 0.0272(6)

_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 1.333(18) . ?
C1 C5 1.390(18) . ?
C1 H1 0.9300 . ?
C2 N1 1.308(17) . ?
C2 C3 1.39(2) . ?
C2 H2 0.9300 . ?
C3 C4 1.36(2) . ?
C3 H3 0.9300 . ?
C4 C5 1.349(18) . ?
C4 H4 0.9300 . ?
C5 C6 1.490(19) . ?
C6 O1 1.240(16) . ?
C6 N2 1.371(17) . ?
C7 C8 1.376(19) . ?
C7 C12 1.381(18) . ?
C7 N2 1.400(16) . ?
C8 C9 1.366(19) . ?
C8 H8 0.9300 . ?
C9 C10 1.364(18) . ?
C9 I1 2.113(14) . ?
C10 C11 1.36(2) . ?
C10 H10 0.9300 . ?
C11 C12 1.40(2) . ?
C11 H11 0.9300 . ?
C12 H12 0.9300 . ?
N1 Hg1 2.503(12) . ?
N2 H2A 0.8600 . ?
Hg1 I3 2.6200(11) . ?
Hg1 I2 2.6387(11) . ?
Hg2 I4 2.5881(11) 3_757 ?
Hg2 I4 2.5881(11) . ?

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 C5 121.7(13) . . ?
N1 C1 H1 119.2 . . ?
C5 C1 H1 119.2 . . ?
N1 C2 C3 120.0(14) . . ?
N1 C2 H2 120.0 . . ?
C3 C2 H2 120.0 . . ?
C4 C3 C2 121.0(14) . . ?
C4 C3 H3 119.5 . . ?
C2 C3 H3 119.5 . . ?
C5 C4 C3 118.3(14) . . ?
C5 C4 H4 120.8 . . ?
C3 C4 H4 120.8 . . ?
C4 C5 C1 119.0(13) . . ?
C4 C5 C6 124.3(13) . . ?
C1 C5 C6 116.7(12) . . ?
O1 C6 N2 122.5(13) . . ?
O1 C6 C5 122.0(13) . . ?
N2 C6 C5 115.3(12) . . ?
C8 C7 C12 119.4(13) . . ?
C8 C7 N2 118.0(12) . . ?
C12 C7 N2 122.5(12) . . ?
C9 C8 C7 120.9(12) . . ?
C9 C8 H8 119.5 . . ?
C7 C8 H8 119.5 . . ?
C10 C9 C8 120.6(13) . . ?
C10 C9 I1 120.9(11) . . ?
C8 C9 I1 118.5(10) . . ?
C9 C10 C11 119.1(13) . . ?
C9 C10 H10 120.4 . . ?
C11 C10 H10 120.4 . . ?
C10 C11 C12 121.3(13) . . ?
C10 C11 H11 119.4 . . ?
C12 C11 H11 119.4 . . ?
C7 C12 C11 118.5(13) . . ?
C7 C12 H12 120.7 . . ?
C11 C12 H12 120.7 . . ?
C2 N1 C1 119.9(13) . . ?
C2 N1 Hg1 117.6(10) . . ?
C1 N1 Hg1 122.3(9) . . ?
C6 N2 C7 127.9(11) . . ?
C6 N2 H2A 116.1 . . ?
C7 N2 H2A 116.1 . . ?
N1 Hg1 I3 101.5(3) . . ?
N1 Hg1 I2 98.6(3) . . ?
I3 Hg1 I2 159.28(4) . . ?
I4 Hg2 I4 179.999(1) 3_757 . ?

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 C2 C3 C4 3(2) . . . . ?
C2 C3 C4 C5 -2(2) . . . . ?
C3 C4 C5 C1 0(2) . . . . ?
C3 C4 C5 C6 -178.6(13) . . . . ?
N1 C1 C5 C4 1(2) . . . . ?
N1 C1 C5 C6 179.3(13) . . . . ?
C4 C5 C6 O1 139.5(15) . . . . ?
C1 C5 C6 O1 -38.9(19) . . . . ?
C4 C5 C6 N2 -36.6(18) . . . . ?
C1 C5 C6 N2 144.9(13) . . . . ?
C12 C7 C8 C9 -0.9(19) . . . . ?
N2 C7 C8 C9 -178.8(11) . . . . ?
C7 C8 C9 C10 0.8(19) . . . . ?
C7 C8 C9 I1 -178.8(9) . . . . ?
C8 C9 C10 C11 2(2) . . . . ?
I1 C9 C10 C11 -178.8(11) . . . . ?
C9 C10 C11 C12 -4(2) . . . . ?
C8 C7 C12 C11 -1.3(19) . . . . ?
N2 C7 C12 C11 176.5(12) . . . . ?
C10 C11 C12 C7 4(2) . . . . ?
C3 C2 N1 C1 -3(2) . . . . ?
C3 C2 N1 Hg1 -177.7(12) . . . . ?
C5 C1 N1 C2 1(2) . . . . ?
C5 C1 N1 Hg1 175.5(10) . . . . ?
O1 C6 N2 C7 -3(2) . . . . ?
C5 C6 N2 C7 172.9(11) . . . . ?
C8 C7 N2 C6 -146.4(13) . . . . ?
C12 C7 N2 C6 36(2) . . . . ?
C2 N1 Hg1 I3 -2.2(11) . . . . ?
C1 N1 Hg1 I3 -177.2(11) . . . . ?
C2 N1 Hg1 I2 -177.3(10) . . . . ?
C1 N1 Hg1 I2 7.7(12) . . . . ?

_diffrn_measured_fraction_theta_max 0.987
_diffrn_reflns_theta_full        29.28
_diffrn_measured_fraction_theta_full 0.987
_refine_diff_density_max         1.356
_refine_diff_density_min         -1.418
_refine_diff_density_rms         0.273
####################################################################### 
# 
# 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\868\kh868
_database_code_depnum_ccdc_archive 'CCDC 991767'
_audit_update_record             
;
2014-03-14 deposited with the CCDC.	2024-01-03 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C24 H18 Br2 Hg3 I6 N4 O2'
_chemical_formula_weight         1917.39

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Hg Hg -2.3894 9.2266 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Br Br -0.2901 2.4595 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
I I -0.4742 1.8119 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_symmetry_cell_setting           Monoclinic
_symmetry_space_group_name_H-M   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                   4.5326(4)
_cell_length_b                   21.4340(12)
_cell_length_c                   19.1582(16)
_cell_angle_alpha                90.00
_cell_angle_beta                 92.076(7)
_cell_angle_gamma                90.00
_cell_volume                     1860.0(2)
_cell_formula_units_Z            2
_cell_measurement_temperature    298(2)
_cell_measurement_reflns_used    20418
_cell_measurement_theta_min      1.90
_cell_measurement_theta_max      29.20

_exptl_crystal_description       Needle
_exptl_crystal_colour            Colorless
_exptl_crystal_size_max          0.50
_exptl_crystal_size_mid          0.06
_exptl_crystal_size_min          0.05
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    3.424
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1668
_exptl_absorpt_coefficient_mu    19.507
_exptl_absorpt_correction_type   numerical
_exptl_absorpt_correction_T_min  0.2651
_exptl_absorpt_correction_T_max  0.4001
_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            20418
_diffrn_reflns_av_R_equivalents  0.0998
_diffrn_reflns_av_sigmaI/netI    0.0944
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_k_min       -26
_diffrn_reflns_limit_k_max       29
_diffrn_reflns_limit_l_min       -26
_diffrn_reflns_limit_l_max       26
_diffrn_reflns_theta_min         1.90
_diffrn_reflns_theta_max         29.20
_reflns_number_total             5005
_reflns_number_gt                3599
_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)+(0.0429P)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    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         5005
_refine_ls_number_parameters     187
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0800
_refine_ls_R_factor_gt           0.0528
_refine_ls_wR_factor_ref         0.1283
_refine_ls_wR_factor_gt          0.1174
_refine_ls_goodness_of_fit_ref   1.028
_refine_ls_restrained_S_all      1.028
_refine_ls_shift/su_max          0.006
_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 0.456(2) 0.1541(5) 0.3220(5) 0.040(2) Uani 1 1 d . . .
H1 H 0.3317 0.1204 0.3125 0.048 Uiso 1 1 calc R . .
C2 C 0.730(3) 0.2352(5) 0.2806(5) 0.045(2) Uani 1 1 d . . .
H2 H 0.8070 0.2567 0.2432 0.054 Uiso 1 1 calc R . .
C3 C 0.810(3) 0.2532(5) 0.3471(6) 0.050(3) Uani 1 1 d . . .
H3 H 0.9245 0.2887 0.3547 0.060 Uiso 1 1 calc R . .
C4 C 0.716(3) 0.2175(5) 0.4041(5) 0.049(3) Uani 1 1 d . . .
H4 H 0.7737 0.2279 0.4498 0.058 Uiso 1 1 calc R . .
C5 C 0.535(2) 0.1664(4) 0.3897(5) 0.037(2) Uani 1 1 d . . .
C6 C 0.4100(19) 0.1282(5) 0.4478(5) 0.038(2) Uani 1 1 d . . .
C7 C 0.5262(19) 0.0888(4) 0.5671(4) 0.0326(18) Uani 1 1 d . . .
C8 C 0.6715(18) 0.1103(4) 0.6261(5) 0.0325(18) Uani 1 1 d . . .
H8 H 0.8057 0.1430 0.6237 0.039 Uiso 1 1 calc R . .
C9 C 0.616(2) 0.0826(5) 0.6888(5) 0.040(2) Uani 1 1 d . . .
C10 C 0.418(2) 0.0332(5) 0.6945(5) 0.045(2) Uani 1 1 d . . .
H10 H 0.3792 0.0152 0.7374 0.054 Uiso 1 1 calc R . .
C11 C 0.284(3) 0.0123(5) 0.6331(6) 0.051(3) Uani 1 1 d . . .
H11 H 0.1544 -0.0213 0.6348 0.061 Uiso 1 1 calc R . .
C12 C 0.332(2) 0.0387(5) 0.5710(5) 0.041(2) Uani 1 1 d . . .
H12 H 0.2370 0.0235 0.5307 0.049 Uiso 1 1 calc R . .
N1 N 0.5483(19) 0.1881(4) 0.2680(4) 0.0411(18) Uani 1 1 d . . .
N2 N 0.5950(16) 0.1178(4) 0.5015(4) 0.0386(18) Uani 1 1 d . . .
H2A H 0.7748 0.1295 0.4970 0.046 Uiso 1 1 calc R . .
O1 O 0.1587(14) 0.1089(4) 0.4418(4) 0.0491(18) Uani 1 1 d . . .
Hg1 Hg 0.43520(10) 0.15644(2) 0.14500(2) 0.04961(14) Uani 1 1 d . . .
Hg2 Hg 0.0000 0.0000 0.0000 0.0715(2) Uani 1 2 d S . .
Br1 Br 0.8062(3) 0.11458(6) 0.77157(6) 0.0598(3) Uani 1 1 d . . .
I1 I 0.05558(14) 0.06632(3) 0.16782(3) 0.04209(16) Uani 1 1 d . . .
I2 I 0.73778(15) 0.23987(3) 0.07749(4) 0.04787(18) Uani 1 1 d . . .
I3 I 0.34079(19) 0.08541(4) -0.04855(5) 0.0647(2) Uani 1 1 d . . .

loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_23
_atom_site_aniso_U_13
_atom_site_aniso_U_12
C1 0.042(5) 0.044(5) 0.033(4) -0.005(4) 0.005(4) -0.012(4)
C2 0.064(6) 0.041(5) 0.029(4) 0.009(4) 0.004(5) -0.006(5)
C3 0.066(7) 0.036(5) 0.050(6) -0.002(4) 0.012(6) -0.016(5)
C4 0.065(7) 0.047(6) 0.034(5) 0.003(4) 0.001(5) -0.012(5)
C5 0.041(5) 0.041(5) 0.031(4) -0.003(4) 0.001(4) 0.005(4)
C6 0.030(4) 0.053(6) 0.031(4) 0.002(4) 0.017(4) 0.001(4)
C7 0.033(4) 0.035(4) 0.031(4) 0.002(3) 0.016(4) 0.001(4)
C8 0.024(4) 0.033(4) 0.041(5) 0.000(3) 0.013(4) 0.002(3)
C9 0.043(5) 0.044(5) 0.033(4) 0.003(4) 0.010(4) 0.016(4)
C10 0.048(5) 0.048(6) 0.040(5) 0.011(4) 0.014(5) 0.000(5)
C11 0.060(7) 0.040(5) 0.053(6) 0.009(5) 0.011(6) -0.001(5)
C12 0.034(4) 0.050(5) 0.038(5) -0.003(4) 0.008(4) -0.006(4)
N1 0.052(5) 0.042(4) 0.030(4) -0.001(3) 0.006(4) -0.005(4)
N2 0.024(3) 0.060(5) 0.032(4) 0.009(3) 0.010(3) 0.002(3)
O1 0.029(3) 0.077(5) 0.042(4) 0.010(4) 0.005(3) -0.005(3)
Hg1 0.0597(3) 0.0499(2) 0.0400(2) 0.00237(16) 0.01200(19) -0.0203(2)
Hg2 0.0797(5) 0.0693(5) 0.0670(4) 0.0022(4) 0.0223(4) -0.0328(4)
Br1 0.0801(8) 0.0654(7) 0.0341(5) -0.0034(5) 0.0043(6) 0.0035(6)
I1 0.0432(3) 0.0419(3) 0.0414(3) 0.0059(3) 0.0056(3) -0.0091(3)
I2 0.0465(4) 0.0489(4) 0.0487(4) 0.0164(3) 0.0086(3) -0.0080(3)
I3 0.0706(5) 0.0641(5) 0.0599(5) 0.0124(4) 0.0112(4) -0.0248(4)

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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
C1 N1 1.345(12) . ?
C1 C5 1.359(13) . ?
C1 H1 0.9300 . ?
C2 N1 1.320(13) . ?
C2 C3 1.367(14) . ?
C2 H2 0.9300 . ?
C3 C4 1.411(14) . ?
C3 H3 0.9300 . ?
C4 C5 1.391(14) . ?
C4 H4 0.9300 . ?
C5 C6 1.510(13) . ?
C6 O1 1.214(11) . ?
C6 N2 1.322(12) . ?
C7 C8 1.366(12) . ?
C7 C12 1.390(13) . ?
C7 N2 1.446(11) . ?
C8 C9 1.372(13) . ?
C8 H8 0.9300 . ?
C9 C10 1.394(14) . ?
C9 Br1 1.906(10) . ?
C10 C11 1.378(16) . ?
C10 H10 0.9300 . ?
C11 C12 1.344(15) . ?
C11 H11 0.9300 . ?
C12 H12 0.9300 . ?
N1 Hg1 2.487(8) . ?
N2 H2A 0.8600 . ?
Hg1 I2 2.6230(7) . ?
Hg1 I1 2.6339(7) . ?
Hg2 I3 2.5897(8) . ?
Hg2 I3 2.5897(8) 3 ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
N1 C1 C5 123.4(9) . . ?
N1 C1 H1 118.3 . . ?
C5 C1 H1 118.3 . . ?
N1 C2 C3 121.9(9) . . ?
N1 C2 H2 119.1 . . ?
C3 C2 H2 119.1 . . ?
C2 C3 C4 119.5(9) . . ?
C2 C3 H3 120.3 . . ?
C4 C3 H3 120.3 . . ?
C5 C4 C3 117.7(9) . . ?
C5 C4 H4 121.1 . . ?
C3 C4 H4 121.1 . . ?
C1 C5 C4 118.4(9) . . ?
C1 C5 C6 120.4(8) . . ?
C4 C5 C6 121.1(9) . . ?
O1 C6 N2 125.7(9) . . ?
O1 C6 C5 119.4(9) . . ?
N2 C6 C5 114.9(8) . . ?
C8 C7 C12 120.2(8) . . ?
C8 C7 N2 117.4(8) . . ?
C12 C7 N2 122.3(8) . . ?
C7 C8 C9 118.6(9) . . ?
C7 C8 H8 120.7 . . ?
C9 C8 H8 120.7 . . ?
C8 C9 C10 122.5(9) . . ?
C8 C9 Br1 118.7(8) . . ?
C10 C9 Br1 118.8(7) . . ?
C11 C10 C9 116.4(9) . . ?
C11 C10 H10 121.8 . . ?
C9 C10 H10 121.8 . . ?
C12 C11 C10 122.5(11) . . ?
C12 C11 H11 118.8 . . ?
C10 C11 H11 118.8 . . ?
C11 C12 C7 119.8(10) . . ?
C11 C12 H12 120.1 . . ?
C7 C12 H12 120.1 . . ?
C2 N1 C1 118.9(8) . . ?
C2 N1 Hg1 119.2(6) . . ?
C1 N1 Hg1 121.5(6) . . ?
C6 N2 C7 126.7(8) . . ?
C6 N2 H2A 116.7 . . ?
C7 N2 H2A 116.7 . . ?
N1 Hg1 I2 100.82(19) . . ?
N1 Hg1 I1 98.99(19) . . ?
I2 Hg1 I1 159.75(3) . . ?
I3 Hg2 I3 180.0 . 3 ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
N1 C2 C3 C4 5.6(18) . . . . ?
C2 C3 C4 C5 -2.6(18) . . . . ?
N1 C1 C5 C4 1.3(16) . . . . ?
N1 C1 C5 C6 176.8(9) . . . . ?
C3 C4 C5 C1 -0.7(16) . . . . ?
C3 C4 C5 C6 -176.2(10) . . . . ?
C1 C5 C6 O1 -34.4(14) . . . . ?
C4 C5 C6 O1 141.0(11) . . . . ?
C1 C5 C6 N2 144.2(9) . . . . ?
C4 C5 C6 N2 -40.4(13) . . . . ?
C12 C7 C8 C9 -1.8(13) . . . . ?
N2 C7 C8 C9 -178.5(8) . . . . ?
C7 C8 C9 C10 0.6(14) . . . . ?
C7 C8 C9 Br1 -177.6(6) . . . . ?
C8 C9 C10 C11 1.1(15) . . . . ?
Br1 C9 C10 C11 179.3(8) . . . . ?
C9 C10 C11 C12 -1.6(16) . . . . ?
C10 C11 C12 C7 0.3(17) . . . . ?
C8 C7 C12 C11 1.4(15) . . . . ?
N2 C7 C12 C11 177.9(9) . . . . ?
C3 C2 N1 C1 -5.1(16) . . . . ?
C3 C2 N1 Hg1 -177.5(9) . . . . ?
C5 C1 N1 C2 1.6(16) . . . . ?
C5 C1 N1 Hg1 173.8(7) . . . . ?
O1 C6 N2 C7 -8.7(17) . . . . ?
C5 C6 N2 C7 172.8(8) . . . . ?
C8 C7 N2 C6 -145.1(10) . . . . ?
C12 C7 N2 C6 38.3(14) . . . . ?
C2 N1 Hg1 I2 -2.1(8) . . . . ?
C1 N1 Hg1 I2 -174.4(8) . . . . ?
C2 N1 Hg1 I1 -177.9(7) . . . . ?
C1 N1 Hg1 I1 9.9(8) . . . . ?

_diffrn_measured_fraction_theta_max 0.993
_diffrn_reflns_theta_full        29.20
_diffrn_measured_fraction_theta_full 0.993
_refine_diff_density_max         1.529
_refine_diff_density_min         -1.505
_refine_diff_density_rms         0.271
####################################################################### 
# 
# 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\799-c2c\kh799
_database_code_depnum_ccdc_archive 'CCDC 1016669'
_audit_update_record             
;
2014-07-28 deposited with the CCDC.	2024-01-03 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C24 H18 Cl2 Hg1 I2 N4 O2'
_chemical_formula_weight         919.71

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'
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           Monoclinic
_symmetry_space_group_name_H-M   C2/c

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

_cell_length_a                   38.520(7)
_cell_length_b                   4.8018(8)
_cell_length_c                   14.841(2)
_cell_angle_alpha                90.00
_cell_angle_beta                 100.118(13)
_cell_angle_gamma                90.00
_cell_volume                     2702.4(8)
_cell_formula_units_Z            4
_cell_measurement_temperature    298(2)
_cell_measurement_reflns_used    14631
_cell_measurement_theta_min      2.15
_cell_measurement_theta_max      29.26

_exptl_crystal_description       Needle
_exptl_crystal_colour            Colorless
_exptl_crystal_size_max          0.45
_exptl_crystal_size_mid          0.10
_exptl_crystal_size_min          0.06
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    2.261
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             17.4
_exptl_absorpt_coefficient_mu    8.207
_exptl_absorpt_correction_type   numerical
_exptl_absorpt_correction_T_min  0.402
_exptl_absorpt_correction_T_max  0.671
_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            14631
_diffrn_reflns_av_R_equivalents  0.0945
_diffrn_reflns_av_sigmaI/netI    0.0845
_diffrn_reflns_limit_h_min       -51
_diffrn_reflns_limit_h_max       52
_diffrn_reflns_limit_k_min       -6
_diffrn_reflns_limit_k_max       6
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_theta_min         2.15
_diffrn_reflns_theta_max         29.26
_reflns_number_total             3659
_reflns_number_gt                1883
_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)+(0.0565P)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         3659
_refine_ls_number_parameters     159
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1476
_refine_ls_R_factor_gt           0.0719
_refine_ls_wR_factor_ref         0.1426
_refine_ls_wR_factor_gt          0.1196
_refine_ls_goodness_of_fit_ref   0.909
_refine_ls_restrained_S_all      0.909
_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 0.0689(3) 1.367(2) 0.2940(8) 0.037(3) Uani 1 1 d . . .
H1 H 0.0707 1.2941 0.2369 0.045 Uiso 1 1 calc R . .
C2 C 0.0404(4) 1.387(3) 0.4169(8) 0.047(3) Uani 1 1 d . . .
H2 H 0.0225 1.3257 0.4468 0.056 Uiso 1 1 calc R . .
C3 C 0.0634(4) 1.586(3) 0.4583(9) 0.052(3) Uani 1 1 d . . .
H3 H 0.0614 1.6553 0.5157 0.062 Uiso 1 1 calc R . .
C4 C 0.0891(4) 1.680(2) 0.4145(10) 0.053(3) Uani 1 1 d . . .
H4 H 0.1038 1.8240 0.4394 0.063 Uiso 1 1 calc R . .
C5 C 0.0934(3) 1.559(2) 0.3319(8) 0.039(3) Uani 1 1 d . . .
C6 C 0.1207(3) 1.668(2) 0.2801(9) 0.046(3) Uani 1 1 d . . .
C7 C 0.1564(3) 1.546(2) 0.1655(8) 0.041(3) Uani 1 1 d . . .
C8 C 0.1887(3) 1.416(2) 0.1756(8) 0.039(3) Uani 1 1 d . . .
H8 H 0.1953 1.2867 0.2221 0.047 Uiso 1 1 calc R . .
C9 C 0.2108(3) 1.481(2) 0.1159(9) 0.046(3) Uani 1 1 d . . .
C10 C 0.2016(4) 1.667(3) 0.0456(9) 0.049(3) Uani 1 1 d . . .
H10 H 0.2168 1.7091 0.0054 0.058 Uiso 1 1 calc R . .
C11 C 0.1686(4) 1.790(3) 0.0370(11) 0.066(4) Uani 1 1 d . . .
H11 H 0.1616 1.9162 -0.0104 0.079 Uiso 1 1 calc R . .
C12 C 0.1460(3) 1.732(3) 0.0965(10) 0.053(3) Uani 1 1 d . . .
H12 H 0.1240 1.8169 0.0899 0.063 Uiso 1 1 calc R . .
N1 N 0.0426(2) 1.2778(18) 0.3347(6) 0.034(2) Uani 1 1 d . . .
N2 N 0.1328(3) 1.4810(17) 0.2270(7) 0.045(3) Uani 1 1 d . . .
H2B H 0.1260 1.3111 0.2298 0.055 Uiso 1 1 calc R . .
O1 O 0.1297(3) 1.9107(17) 0.2854(7) 0.063(3) Uani 1 1 d . . .
Hg1 Hg 0.0000 0.95624(14) 0.2500 0.0384(2) Uani 1 2 d S . .
Cl1 Cl 0.03267(9) 0.8504(7) 0.1343(2) 0.0536(8) Uani 1 1 d . . .
I1 I 0.26249(3) 1.3175(2) 0.13876(7) 0.0612(3) Uani 1 1 d . . .

loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_23
_atom_site_aniso_U_13
_atom_site_aniso_U_12
C1 0.040(7) 0.027(6) 0.046(7) -0.004(5) 0.010(6) -0.003(5)
C2 0.050(8) 0.056(8) 0.037(7) 0.007(6) 0.015(6) 0.005(6)
C3 0.065(9) 0.056(8) 0.036(7) -0.016(6) 0.016(6) -0.014(7)
C4 0.066(10) 0.029(6) 0.061(9) -0.008(6) 0.007(7) -0.013(6)
C5 0.041(7) 0.026(5) 0.049(7) -0.003(6) 0.008(5) 0.005(5)
C6 0.055(8) 0.028(6) 0.063(9) 0.000(6) 0.033(7) 0.004(5)
C7 0.051(7) 0.036(6) 0.037(6) 0.002(5) 0.016(5) 0.001(6)
C8 0.050(7) 0.024(6) 0.045(7) 0.008(5) 0.013(6) 0.007(5)
C9 0.042(7) 0.046(8) 0.049(7) 0.010(6) 0.006(6) 0.004(6)
C10 0.047(8) 0.053(7) 0.052(8) 0.008(6) 0.022(6) 0.009(6)
C11 0.058(10) 0.071(10) 0.070(10) 0.022(8) 0.015(8) 0.006(8)
C12 0.027(7) 0.057(8) 0.074(10) 0.011(7) 0.009(7) 0.000(6)
N1 0.033(5) 0.036(5) 0.037(5) 0.001(4) 0.016(4) -0.005(4)
N2 0.064(7) 0.017(5) 0.060(7) 0.007(4) 0.023(5) -0.010(4)
O1 0.078(7) 0.026(5) 0.096(8) -0.002(4) 0.042(6) -0.007(4)
Hg1 0.0371(4) 0.0395(4) 0.0399(4) 0.000 0.0103(3) 0.000
Cl1 0.056(2) 0.061(2) 0.0471(19) -0.0094(15) 0.0175(16) 0.0070(15)
I1 0.0521(6) 0.0726(7) 0.0618(7) 0.0063(5) 0.0182(5) 0.0134(4)

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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
C1 N1 1.338(14) . ?
C1 C5 1.368(16) . ?
C1 H1 0.9300 . ?
C2 N1 1.345(15) . ?
C2 C3 1.373(18) . ?
C2 H2 0.9300 . ?
C3 C4 1.352(18) . ?
C3 H3 0.9300 . ?
C4 C5 1.390(18) . ?
C4 H4 0.9300 . ?
C5 C6 1.502(17) . ?
C6 O1 1.214(14) . ?
C6 N2 1.332(15) . ?
C7 C12 1.364(17) . ?
C7 C8 1.374(16) . ?
C7 N2 1.433(15) . ?
C8 C9 1.370(17) . ?
C8 H8 0.9300 . ?
C9 C10 1.372(17) . ?
C9 I1 2.112(12) . ?
C10 C11 1.386(19) . ?
C10 H10 0.9300 . ?
C11 C12 1.376(19) . ?
C11 H11 0.9300 . ?
C12 H12 0.9300 . ?
N1 Hg1 2.437(9) . ?
N2 H2B 0.8600 . ?
Hg1 Cl1 2.356(3) 2 ?
Hg1 Cl1 2.356(3) . ?
Hg1 N1 2.437(9) 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 C5 123.4(11) . . ?
N1 C1 H1 118.3 . . ?
C5 C1 H1 118.3 . . ?
N1 C2 C3 122.5(11) . . ?
N1 C2 H2 118.7 . . ?
C3 C2 H2 118.7 . . ?
C4 C3 C2 119.0(12) . . ?
C4 C3 H3 120.5 . . ?
C2 C3 H3 120.5 . . ?
C3 C4 C5 119.8(12) . . ?
C3 C4 H4 120.1 . . ?
C5 C4 H4 120.1 . . ?
C1 C5 C4 117.6(11) . . ?
C1 C5 C6 121.2(11) . . ?
C4 C5 C6 120.6(11) . . ?
O1 C6 N2 124.1(11) . . ?
O1 C6 C5 121.2(11) . . ?
N2 C6 C5 114.7(10) . . ?
C12 C7 C8 121.4(11) . . ?
C12 C7 N2 118.9(11) . . ?
C8 C7 N2 119.7(10) . . ?
C9 C8 C7 118.6(10) . . ?
C9 C8 H8 120.7 . . ?
C7 C8 H8 120.7 . . ?
C8 C9 C10 122.3(11) . . ?
C8 C9 I1 119.1(8) . . ?
C10 C9 I1 118.4(9) . . ?
C9 C10 C11 117.3(12) . . ?
C9 C10 H10 121.4 . . ?
C11 C10 H10 121.4 . . ?
C12 C11 C10 121.8(13) . . ?
C12 C11 H11 119.1 . . ?
C10 C11 H11 119.1 . . ?
C7 C12 C11 118.7(12) . . ?
C7 C12 H12 120.7 . . ?
C11 C12 H12 120.7 . . ?
C1 N1 C2 117.4(10) . . ?
C1 N1 Hg1 117.7(7) . . ?
C2 N1 Hg1 124.7(8) . . ?
C6 N2 C7 123.9(9) . . ?
C6 N2 H2B 118.0 . . ?
C7 N2 H2B 118.0 . . ?
Cl1 Hg1 Cl1 155.08(17) 2 . ?
Cl1 Hg1 N1 99.1(2) 2 . ?
Cl1 Hg1 N1 96.6(2) . . ?
Cl1 Hg1 N1 96.6(2) 2 2 ?
Cl1 Hg1 N1 99.1(2) . 2 ?
N1 Hg1 N1 101.4(4) . 2 ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
N1 C2 C3 C4 1(2) . . . . ?
C2 C3 C4 C5 -5(2) . . . . ?
N1 C1 C5 C4 -4.1(18) . . . . ?
N1 C1 C5 C6 -175.3(11) . . . . ?
C3 C4 C5 C1 6.2(19) . . . . ?
C3 C4 C5 C6 177.5(12) . . . . ?
C1 C5 C6 O1 141.7(14) . . . . ?
C4 C5 C6 O1 -29(2) . . . . ?
C1 C5 C6 N2 -36.0(17) . . . . ?
C4 C5 C6 N2 153.1(12) . . . . ?
C12 C7 C8 C9 1.3(19) . . . . ?
N2 C7 C8 C9 179.9(11) . . . . ?
C7 C8 C9 C10 -1.2(19) . . . . ?
C7 C8 C9 I1 173.5(9) . . . . ?
C8 C9 C10 C11 0(2) . . . . ?
I1 C9 C10 C11 -174.4(11) . . . . ?
C9 C10 C11 C12 1(2) . . . . ?
C8 C7 C12 C11 -1(2) . . . . ?
N2 C7 C12 C11 -179.2(12) . . . . ?
C10 C11 C12 C7 0(2) . . . . ?
C5 C1 N1 C2 0.5(17) . . . . ?
C5 C1 N1 Hg1 176.1(9) . . . . ?
C3 C2 N1 C1 1.1(18) . . . . ?
C3 C2 N1 Hg1 -174.2(10) . . . . ?
O1 C6 N2 C7 -4(2) . . . . ?
C5 C6 N2 C7 174.0(11) . . . . ?
C12 C7 N2 C6 -60.7(18) . . . . ?
C8 C7 N2 C6 120.7(14) . . . . ?
C1 N1 Hg1 Cl1 173.4(7) . . . 2 ?
C2 N1 Hg1 Cl1 -11.3(9) . . . 2 ?
C1 N1 Hg1 Cl1 12.8(8) . . . . ?
C2 N1 Hg1 Cl1 -171.9(9) . . . . ?
C1 N1 Hg1 N1 -87.9(8) . . . 2 ?
C2 N1 Hg1 N1 87.4(9) . . . 2 ?

_diffrn_measured_fraction_theta_max 0.988
_diffrn_reflns_theta_full        29.26
_diffrn_measured_fraction_theta_full 0.988
_refine_diff_density_max         1.537
_refine_diff_density_min         -1.514
_refine_diff_density_rms         0.339
####################################################################### 
# 
# 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\907\kh907-new
_database_code_depnum_ccdc_archive 'CCDC 1016676'
_audit_update_record             
;
2014-07-28 deposited with the CCDC.	2024-01-03 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C12 H9 Cl1 Hg1 I2 N2 O1'
_chemical_formula_weight         687.05

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
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           Monoclinic
_symmetry_space_group_name_H-M   C2/c

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

_cell_length_a                   25.080(6)
_cell_length_b                   14.097(4)
_cell_length_c                   9.200(2)
_cell_angle_alpha                90.00
_cell_angle_beta                 100.394(18)
_cell_angle_gamma                90.00
_cell_volume                     3199.4(13)
_cell_formula_units_Z            8
_cell_measurement_temperature    298(2)
_cell_measurement_reflns_used    9135
_cell_measurement_theta_min      1.66
_cell_measurement_theta_max      27.00

_exptl_crystal_description       Block
_exptl_crystal_colour            Colorless
_exptl_crystal_size_max          0.30
_exptl_crystal_size_mid          0.22
_exptl_crystal_size_min          0.12
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    2.853
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             2448
_exptl_absorpt_coefficient_mu    13.641
_exptl_absorpt_correction_type   numerical
_exptl_absorpt_correction_T_min  0.0228
_exptl_absorpt_correction_T_max  0.2505
_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            9135
_diffrn_reflns_av_R_equivalents  0.0992
_diffrn_reflns_av_sigmaI/netI    0.0948
_diffrn_reflns_limit_h_min       -24
_diffrn_reflns_limit_h_max       32
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_theta_min         1.66
_diffrn_reflns_theta_max         27.00
_reflns_number_total             3494
_reflns_number_gt                1764
_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)+(0.1108P)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         3494
_refine_ls_number_parameters     172
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0986
_refine_ls_R_factor_gt           0.0861
_refine_ls_wR_factor_ref         0.1952
_refine_ls_wR_factor_gt          0.1658
_refine_ls_goodness_of_fit_ref   0.895
_refine_ls_restrained_S_all      0.895
_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 0.1491(8) 0.2590(14) 0.3690(17) 0.042(5) Uani 1 1 d . . .
H1 H 0.1318 0.2517 0.2714 0.051 Uiso 1 1 calc R . .
C2 C 0.1938(10) 0.1941(16) 0.5807(19) 0.054(6) Uani 1 1 d . . .
H2 H 0.2081 0.1402 0.6317 0.065 Uiso 1 1 calc R . .
C3 C 0.2041(9) 0.2806(15) 0.6478(16) 0.048(5) Uani 1 1 d . . .
H3 H 0.2233 0.2854 0.7439 0.057 Uiso 1 1 calc R . .
C4 C 0.1854(7) 0.3585(15) 0.5702(16) 0.040(4) Uani 1 1 d . . .
H4 H 0.1912 0.4182 0.6131 0.048 Uiso 1 1 calc R . .
C5 C 0.1577(7) 0.3496(11) 0.4268(14) 0.028(4) Uani 1 1 d . . .
C6 C 0.1338(8) 0.4308(13) 0.3304(15) 0.035(4) Uani 1 1 d . . .
C7 C 0.0968(9) 0.5927(14) 0.3187(14) 0.047(6) Uani 1 1 d . . .
C8 C 0.0616(7) 0.5850(14) 0.1816(18) 0.039(4) Uani 1 1 d . . .
H8 H 0.0507 0.5257 0.1427 0.047 Uiso 1 1 calc R . .
C9 C 0.0436(8) 0.6667(15) 0.1059(17) 0.043(5) Uani 1 1 d . . .
C10 C 0.0592(9) 0.7539(15) 0.168(2) 0.053(6) Uani 1 1 d . . .
H10 H 0.0485 0.8084 0.1136 0.063 Uiso 1 1 calc R . .
C11 C 0.0895(9) 0.7631(15) 0.306(2) 0.052(6) Uani 1 1 d . . .
H11 H 0.0962 0.8226 0.3490 0.062 Uiso 1 1 calc R . .
C12 C 0.1104(10) 0.6813(15) 0.3802(18) 0.050(6) Uani 1 1 d . . .
H12 H 0.1334 0.6861 0.4712 0.060 Uiso 1 1 calc R . .
N1 N 0.1647(7) 0.1837(10) 0.4473(14) 0.044(4) Uani 1 1 d . . .
N2 N 0.1192(7) 0.5094(11) 0.3928(14) 0.039(4) Uani 1 1 d . . .
H2A H 0.1238 0.5100 0.4877 0.047 Uiso 1 1 calc R . .
O1 O 0.1338(6) 0.4262(10) 0.1947(11) 0.049(4) Uani 1 1 d . . .
Hg1 Hg 0.14887(4) 0.02380(6) 0.35023(9) 0.0601(4) Uani 1 1 d . . .
Cl1 Cl 0.0045(3) 0.6608(5) -0.0681(5) 0.0682(18) Uani 1 1 d . . .
I1 I 0.07031(6) 0.03759(12) 0.12234(14) 0.0603(5) Uani 1 1 d . . .
I2 I 0.22800(7) -0.07797(11) 0.50160(16) 0.0649(5) Uani 1 1 d . . .

loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_23
_atom_site_aniso_U_13
_atom_site_aniso_U_12
C1 0.054(12) 0.045(10) 0.026(7) -0.015(8) 0.007(8) 0.008(10)
C2 0.077(15) 0.040(10) 0.042(9) 0.004(9) -0.002(10) -0.004(11)
C3 0.070(14) 0.051(11) 0.020(7) 0.003(8) 0.001(8) 0.006(11)
C4 0.041(10) 0.049(11) 0.030(7) -0.005(8) 0.007(7) -0.004(10)
C5 0.042(10) 0.024(7) 0.020(6) -0.008(6) 0.015(6) -0.002(8)
C6 0.050(11) 0.033(9) 0.024(7) 0.006(7) 0.009(7) -0.017(9)
C7 0.094(16) 0.037(10) 0.012(6) -0.005(6) 0.016(8) 0.003(11)
C8 0.036(9) 0.038(10) 0.043(8) -0.007(8) 0.007(7) 0.002(9)
C9 0.048(11) 0.047(11) 0.036(8) -0.007(9) 0.018(8) -0.005(10)
C10 0.070(14) 0.045(11) 0.046(9) 0.028(9) 0.016(10) 0.029(11)
C11 0.057(13) 0.035(10) 0.063(12) -0.010(9) 0.009(10) -0.001(10)
C12 0.078(15) 0.040(11) 0.034(8) -0.005(8) 0.016(9) -0.027(11)
N1 0.069(12) 0.025(7) 0.035(7) 0.003(6) -0.001(7) 0.003(8)
N2 0.058(10) 0.031(8) 0.028(6) 0.002(6) 0.007(6) 0.007(8)
O1 0.081(10) 0.040(7) 0.028(5) -0.004(5) 0.015(6) 0.013(8)
Hg1 0.0712(6) 0.0375(4) 0.0608(5) -0.0029(4) -0.0171(4) 0.0036(5)
Cl1 0.079(4) 0.075(4) 0.043(2) 0.003(3) -0.008(3) 0.018(3)
I1 0.0648(9) 0.0615(9) 0.0483(6) 0.0085(7) -0.0067(6) -0.0041(8)
I2 0.0661(10) 0.0507(8) 0.0698(8) 0.0135(7) -0.0100(7) 0.0059(8)

_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 1.30(2) . ?
C1 C5 1.39(2) . ?
C1 H1 0.9300 . ?
C2 N1 1.32(2) . ?
C2 C3 1.37(3) . ?
C2 H2 0.9300 . ?
C3 C4 1.35(3) . ?
C3 H3 0.9300 . ?
C4 C5 1.381(19) . ?
C4 H4 0.9300 . ?
C5 C6 1.51(2) . ?
C6 O1 1.251(19) . ?
C6 N2 1.33(2) . ?
C7 C12 1.39(3) . ?
C7 C8 1.41(2) . ?
C7 N2 1.42(2) . ?
C8 C9 1.38(3) . ?
C8 H8 0.9300 . ?
C9 C10 1.38(3) . ?
C9 Cl1 1.721(16) . ?
C10 C11 1.36(3) . ?
C10 H10 0.9300 . ?
C11 C12 1.39(3) . ?
C11 H11 0.9300 . ?
C12 H12 0.9300 . ?
N1 Hg1 2.430(15) . ?
N2 H2A 0.8600 . ?
Hg1 I1 2.6126(15) . ?
Hg1 I2 2.6342(16) . ?

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 C5 121.9(13) . . ?
N1 C1 H1 119.0 . . ?
C5 C1 H1 119.0 . . ?
N1 C2 C3 123.1(18) . . ?
N1 C2 H2 118.4 . . ?
C3 C2 H2 118.4 . . ?
C4 C3 C2 117.9(14) . . ?
C4 C3 H3 121.0 . . ?
C2 C3 H3 121.0 . . ?
C3 C4 C5 119.9(18) . . ?
C3 C4 H4 120.0 . . ?
C5 C4 H4 120.0 . . ?
C4 C5 C1 117.8(16) . . ?
C4 C5 C6 124.9(16) . . ?
C1 C5 C6 117.2(12) . . ?
O1 C6 N2 121.6(16) . . ?
O1 C6 C5 118.5(17) . . ?
N2 C6 C5 119.4(12) . . ?
C12 C7 C8 120.2(18) . . ?
C12 C7 N2 120.0(15) . . ?
C8 C7 N2 119.7(16) . . ?
C9 C8 C7 118.9(18) . . ?
C9 C8 H8 120.6 . . ?
C7 C8 H8 120.6 . . ?
C8 C9 C10 119.4(15) . . ?
C8 C9 Cl1 120.6(15) . . ?
C10 C9 Cl1 119.9(15) . . ?
C11 C10 C9 122.6(18) . . ?
C11 C10 H10 118.7 . . ?
C9 C10 H10 118.7 . . ?
C10 C11 C12 118.4(18) . . ?
C10 C11 H11 120.8 . . ?
C12 C11 H11 120.8 . . ?
C7 C12 C11 120.1(16) . . ?
C7 C12 H12 120.0 . . ?
C11 C12 H12 120.0 . . ?
C1 N1 C2 118.9(16) . . ?
C1 N1 Hg1 122.7(10) . . ?
C2 N1 Hg1 118.2(12) . . ?
C6 N2 C7 126.7(13) . . ?
C6 N2 H2A 116.7 . . ?
C7 N2 H2A 116.7 . . ?
N1 Hg1 I1 106.0(3) . . ?
N1 Hg1 I2 104.7(3) . . ?
I1 Hg1 I2 148.43(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 C2 C3 C4 -3(4) . . . . ?
C2 C3 C4 C5 -1(3) . . . . ?
C3 C4 C5 C1 1(3) . . . . ?
C3 C4 C5 C6 178(2) . . . . ?
N1 C1 C5 C4 2(3) . . . . ?
N1 C1 C5 C6 -175(2) . . . . ?
C4 C5 C6 O1 145.6(18) . . . . ?
C1 C5 C6 O1 -37(3) . . . . ?
C4 C5 C6 N2 -27(3) . . . . ?
C1 C5 C6 N2 150.4(19) . . . . ?
C12 C7 C8 C9 4(3) . . . . ?
N2 C7 C8 C9 -175(2) . . . . ?
C7 C8 C9 C10 -2(3) . . . . ?
C7 C8 C9 Cl1 175.3(15) . . . . ?
C8 C9 C10 C11 -4(4) . . . . ?
Cl1 C9 C10 C11 179.3(17) . . . . ?
C9 C10 C11 C12 7(4) . . . . ?
C8 C7 C12 C11 -1(4) . . . . ?
N2 C7 C12 C11 178(2) . . . . ?
C10 C11 C12 C7 -5(4) . . . . ?
C5 C1 N1 C2 -6(3) . . . . ?
C5 C1 N1 Hg1 179.0(15) . . . . ?
C3 C2 N1 C1 7(4) . . . . ?
C3 C2 N1 Hg1 -178(2) . . . . ?
O1 C6 N2 C7 7(3) . . . . ?
C5 C6 N2 C7 179(2) . . . . ?
C12 C7 N2 C6 -144(2) . . . . ?
C8 C7 N2 C6 35(3) . . . . ?
C1 N1 Hg1 I1 -20.1(19) . . . . ?
C2 N1 Hg1 I1 165.3(16) . . . . ?
C1 N1 Hg1 I2 152.3(17) . . . . ?
C2 N1 Hg1 I2 -22.3(17) . . . . ?

_diffrn_measured_fraction_theta_max 0.999
_diffrn_reflns_theta_full        27.00
_diffrn_measured_fraction_theta_full 0.999
_refine_diff_density_max         1.251
_refine_diff_density_min         -1.305
_refine_diff_density_rms         0.494
####################################################################### 
# 
# 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\b22\khb22
_audit_block_doi                 10.5517/cc1290m0
_database_code_depnum_ccdc_archive 'CCDC 991771'
loop_
_citation_id
_citation_doi
_citation_year
1 10.1039/C4CE00692E 2014
_audit_update_record             
;
2014-03-14 deposited with the CCDC.	2024-01-03 downloaded from the CCDC.
;

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

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Hg Hg -2.3894 9.2266 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Br Br -0.2901 2.4595 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
I I -0.4742 1.8119 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_symmetry_cell_setting           Monoclinic
_symmetry_space_group_name_H-M   C2/c

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

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

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

_exptl_special_details           
; 
 ? 
;

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

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

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

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

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

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

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

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

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

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

_diffrn_measured_fraction_theta_max 0.996
_diffrn_reflns_theta_full        28.00
_diffrn_measured_fraction_theta_full 0.996
_refine_diff_density_max         1.254
_refine_diff_density_min         -1.251
_refine_diff_density_rms         0.231
####################################################################### 
# 
# 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\901\kh901
_database_code_depnum_ccdc_archive 'CCDC 1016674'
_audit_update_record             
;
2014-07-28 deposited with the CCDC.	2024-01-03 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C24 H18 Br4 Hg1 N4 O2'
_chemical_formula_weight         914.61

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

_symmetry_cell_setting           Monoclinic
_symmetry_space_group_name_H-M   C2/c

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

_cell_length_a                   23.569(3)
_cell_length_b                   4.9189(4)
_cell_length_c                   27.722(3)
_cell_angle_alpha                90.00
_cell_angle_beta                 124.465(7)
_cell_angle_gamma                90.00
_cell_volume                     2649.8(5)
_cell_formula_units_Z            4
_cell_measurement_temperature    298(2)
_cell_measurement_reflns_used    10150
_cell_measurement_theta_min      1.78
_cell_measurement_theta_max      29.21

_exptl_crystal_description       Plate
_exptl_crystal_colour            Colorless
_exptl_crystal_size_max          0.25
_exptl_crystal_size_mid          0.10
_exptl_crystal_size_min          0.09
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    2.293
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1704
_exptl_absorpt_coefficient_mu    11.870
_exptl_absorpt_correction_type   numerical
_exptl_absorpt_correction_T_min  0.2841
_exptl_absorpt_correction_T_max  0.3581
_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            10150
_diffrn_reflns_av_R_equivalents  0.1032
_diffrn_reflns_av_sigmaI/netI    0.0901
_diffrn_reflns_limit_h_min       -32
_diffrn_reflns_limit_h_max       32
_diffrn_reflns_limit_k_min       -6
_diffrn_reflns_limit_k_max       6
_diffrn_reflns_limit_l_min       -37
_diffrn_reflns_limit_l_max       31
_diffrn_reflns_theta_min         1.78
_diffrn_reflns_theta_max         29.21
_reflns_number_total             3561
_reflns_number_gt                2166
_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)+(0.0891P)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         3561
_refine_ls_number_parameters     159
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0909
_refine_ls_R_factor_gt           0.0705
_refine_ls_wR_factor_ref         0.1761
_refine_ls_wR_factor_gt          0.1562
_refine_ls_goodness_of_fit_ref   1.011
_refine_ls_restrained_S_all      1.011
_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 -0.1010(5) 0.391(2) 0.1339(4) 0.045(2) Uani 1 1 d . . .
H1 H -0.0745 0.3002 0.1239 0.054 Uiso 1 1 calc R . .
C2 C -0.1342(6) 0.443(3) 0.1957(5) 0.056(3) Uani 1 1 d . . .
H2 H -0.1309 0.3903 0.2294 0.067 Uiso 1 1 calc R . .
C3 C -0.1813(6) 0.644(3) 0.1610(6) 0.063(3) Uani 1 1 d . . .
H3 H -0.2085 0.7265 0.1713 0.075 Uiso 1 1 calc R . .
C4 C -0.1864(5) 0.717(2) 0.1108(5) 0.058(3) Uani 1 1 d . . .
H4 H -0.2172 0.8518 0.0866 0.069 Uiso 1 1 calc R . .
C5 C -0.1461(5) 0.591(2) 0.0963(4) 0.041(2) Uani 1 1 d . . .
C6 C -0.1480(6) 0.675(2) 0.0437(5) 0.054(3) Uani 1 1 d . . .
C7 C -0.1277(6) 0.528(2) -0.0294(5) 0.054(3) Uani 1 1 d . . .
C8 C -0.1640(6) 0.375(3) -0.0804(5) 0.051(3) Uani 1 1 d . . .
H8 H -0.1949 0.2420 -0.0855 0.061 Uiso 1 1 calc R . .
C9 C -0.1535(6) 0.425(3) -0.1227(5) 0.058(3) Uani 1 1 d . . .
C10 C -0.1066(8) 0.609(4) -0.1173(8) 0.083(4) Uani 1 1 d . . .
H10 H -0.0985 0.6328 -0.1462 0.100 Uiso 1 1 calc R . .
C11 C -0.0718(10) 0.760(4) -0.0655(10) 0.112(7) Uani 1 1 d . . .
H11 H -0.0411 0.8936 -0.0606 0.134 Uiso 1 1 calc R . .
C12 C -0.0811(8) 0.718(3) -0.0222(7) 0.083(5) Uani 1 1 d . . .
H12 H -0.0559 0.8179 0.0123 0.100 Uiso 1 1 calc R . .
N1 N -0.0942(4) 0.3237(19) 0.1833(3) 0.049(2) Uani 1 1 d . . .
N2 N -0.1370(5) 0.479(2) 0.0155(4) 0.052(2) Uani 1 1 d . . .
H2A H -0.1355 0.3135 0.0260 0.063 Uiso 1 1 calc R . .
O1 O -0.1582(5) 0.9147(16) 0.0274(4) 0.062(2) Uani 1 1 d . . .
Br1 Br -0.20563(8) 0.2244(4) -0.19416(6) 0.0880(5) Uani 1 1 d . . .
Br2 Br 0.03403(6) -0.1072(3) 0.18281(5) 0.0605(3) Uani 1 1 d . . .
Hg1 Hg 0.0000 0.00796(14) 0.2500 0.0474(2) Uani 1 2 d S . .

loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_23
_atom_site_aniso_U_13
_atom_site_aniso_U_12
C1 0.048(5) 0.038(5) 0.034(4) 0.004(4) 0.014(4) 0.004(4)
C2 0.053(6) 0.067(9) 0.041(5) -0.001(5) 0.021(5) -0.017(5)
C3 0.051(6) 0.063(9) 0.068(7) 0.005(7) 0.029(6) 0.006(6)
C4 0.042(5) 0.040(6) 0.054(6) -0.003(5) 0.005(5) 0.006(5)
C5 0.046(5) 0.030(5) 0.040(5) -0.005(4) 0.020(4) -0.005(4)
C6 0.060(6) 0.026(6) 0.048(5) -0.004(4) 0.013(5) -0.002(5)
C7 0.061(6) 0.031(6) 0.050(5) 0.008(5) 0.019(5) 0.008(5)
C8 0.057(6) 0.044(6) 0.046(5) 0.004(5) 0.026(5) -0.006(5)
C9 0.056(6) 0.059(8) 0.054(6) 0.016(5) 0.028(5) 0.007(5)
C10 0.096(11) 0.082(11) 0.092(11) 0.019(9) 0.067(9) -0.004(9)
C11 0.123(15) 0.089(14) 0.139(17) -0.008(12) 0.083(14) -0.051(12)
C12 0.087(10) 0.078(11) 0.082(9) -0.024(8) 0.046(8) -0.038(9)
N1 0.046(4) 0.040(6) 0.037(4) 0.001(4) 0.011(4) 0.002(4)
N2 0.072(6) 0.030(5) 0.047(4) 0.008(4) 0.028(4) 0.002(5)
O1 0.081(5) 0.024(4) 0.057(4) 0.005(3) 0.024(4) 0.003(4)
Br1 0.0824(9) 0.1268(16) 0.0534(7) -0.0042(8) 0.0377(7) -0.0004(9)
Br2 0.0642(7) 0.0662(8) 0.0536(6) -0.0001(6) 0.0347(5) 0.0081(6)
Hg1 0.0463(3) 0.0494(4) 0.0362(3) 0.000 0.0173(2) 0.000

_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 1.327(14) . ?
C1 C5 1.388(15) . ?
C1 H1 0.9300 . ?
C2 N1 1.313(15) . ?
C2 C3 1.389(18) . ?
C2 H2 0.9300 . ?
C3 C4 1.375(19) . ?
C3 H3 0.9300 . ?
C4 C5 1.370(17) . ?
C4 H4 0.9300 . ?
C5 C6 1.493(17) . ?
C6 O1 1.234(13) . ?
C6 N2 1.356(15) . ?
C7 C12 1.370(19) . ?
C7 C8 1.388(16) . ?
C7 N2 1.399(17) . ?
C8 C9 1.352(17) . ?
C8 H8 0.9300 . ?
C9 C10 1.37(2) . ?
C9 Br1 1.911(13) . ?
C10 C11 1.40(3) . ?
C10 H10 0.9300 . ?
C11 C12 1.35(2) . ?
C11 H11 0.9300 . ?
C12 H12 0.9300 . ?
N1 Hg1 2.472(8) . ?
N2 H2A 0.8600 . ?
Br2 Hg1 2.4749(13) . ?
Hg1 N1 2.472(8) 2 ?
Hg1 Br2 2.4750(13) 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 C5 123.1(11) . . ?
N1 C1 H1 118.5 . . ?
C5 C1 H1 118.5 . . ?
N1 C2 C3 123.2(11) . . ?
N1 C2 H2 118.4 . . ?
C3 C2 H2 118.4 . . ?
C4 C3 C2 117.7(12) . . ?
C4 C3 H3 121.1 . . ?
C2 C3 H3 121.1 . . ?
C5 C4 C3 120.0(11) . . ?
C5 C4 H4 120.0 . . ?
C3 C4 H4 120.0 . . ?
C4 C5 C1 117.7(10) . . ?
C4 C5 C6 121.2(10) . . ?
C1 C5 C6 121.1(10) . . ?
O1 C6 N2 122.0(12) . . ?
O1 C6 C5 120.9(11) . . ?
N2 C6 C5 117.1(9) . . ?
C12 C7 C8 119.8(13) . . ?
C12 C7 N2 120.2(12) . . ?
C8 C7 N2 120.0(11) . . ?
C9 C8 C7 118.5(12) . . ?
C9 C8 H8 120.7 . . ?
C7 C8 H8 120.7 . . ?
C8 C9 C10 123.8(13) . . ?
C8 C9 Br1 118.6(10) . . ?
C10 C9 Br1 117.6(11) . . ?
C9 C10 C11 115.6(15) . . ?
C9 C10 H10 122.2 . . ?
C11 C10 H10 122.2 . . ?
C12 C11 C10 122.5(15) . . ?
C12 C11 H11 118.8 . . ?
C10 C11 H11 118.8 . . ?
C11 C12 C7 119.6(14) . . ?
C11 C12 H12 120.2 . . ?
C7 C12 H12 120.2 . . ?
C2 N1 C1 118.2(9) . . ?
C2 N1 Hg1 124.0(7) . . ?
C1 N1 Hg1 117.6(7) . . ?
C6 N2 C7 124.7(10) . . ?
C6 N2 H2A 117.7 . . ?
C7 N2 H2A 117.7 . . ?
N1 Hg1 N1 102.2(4) . 2 ?
N1 Hg1 Br2 96.7(2) . . ?
N1 Hg1 Br2 99.8(2) 2 . ?
N1 Hg1 Br2 99.8(2) . 2 ?
N1 Hg1 Br2 96.7(2) 2 2 ?
Br2 Hg1 Br2 153.53(8) . 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 C2 C3 C4 1.0(19) . . . . ?
C2 C3 C4 C5 0.4(18) . . . . ?
C3 C4 C5 C1 0.1(17) . . . . ?
C3 C4 C5 C6 -176.9(10) . . . . ?
N1 C1 C5 C4 -2.0(17) . . . . ?
N1 C1 C5 C6 175.0(10) . . . . ?
C4 C5 C6 O1 33.2(16) . . . . ?
C1 C5 C6 O1 -143.7(11) . . . . ?
C4 C5 C6 N2 -147.8(10) . . . . ?
C1 C5 C6 N2 35.2(15) . . . . ?
C12 C7 C8 C9 -1.8(19) . . . . ?
N2 C7 C8 C9 -179.4(11) . . . . ?
C7 C8 C9 C10 3(2) . . . . ?
C7 C8 C9 Br1 -177.9(9) . . . . ?
C8 C9 C10 C11 -4(3) . . . . ?
Br1 C9 C10 C11 177.3(14) . . . . ?
C9 C10 C11 C12 3(3) . . . . ?
C10 C11 C12 C7 -2(3) . . . . ?
C8 C7 C12 C11 1(2) . . . . ?
N2 C7 C12 C11 179.0(16) . . . . ?
C3 C2 N1 C1 -2.8(17) . . . . ?
C3 C2 N1 Hg1 172.0(9) . . . . ?
C5 C1 N1 C2 3.3(16) . . . . ?
C5 C1 N1 Hg1 -171.8(8) . . . . ?
O1 C6 N2 C7 8.0(18) . . . . ?
C5 C6 N2 C7 -171.0(10) . . . . ?
C12 C7 N2 C6 50.1(18) . . . . ?
C8 C7 N2 C6 -132.3(12) . . . . ?
C2 N1 Hg1 N1 -81.5(8) . . . 2 ?
C1 N1 Hg1 N1 93.4(8) . . . 2 ?
C2 N1 Hg1 Br2 176.9(8) . . . . ?
C1 N1 Hg1 Br2 -8.2(8) . . . . ?
C2 N1 Hg1 Br2 17.7(9) . . . 2 ?
C1 N1 Hg1 Br2 -167.5(7) . . . 2 ?

_diffrn_measured_fraction_theta_max 0.992
_diffrn_reflns_theta_full        29.21
_diffrn_measured_fraction_theta_full 0.992
_refine_diff_density_max         1.815
_refine_diff_density_min         -1.789
_refine_diff_density_rms         0.285
####################################################################### 
# 
# 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\903-2\kh903-2
_database_code_depnum_ccdc_archive 'CCDC 1016675'
_audit_update_record             
;
2014-07-28 deposited with the CCDC.	2024-01-03 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C24 H18 Br2 Cl2 Hg1 N4 O2'
_chemical_formula_weight         825.71

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'
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'
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   C2/c

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

_cell_length_a                   23.266(3)
_cell_length_b                   4.9212(4)
_cell_length_c                   27.288(3)
_cell_angle_alpha                90.00
_cell_angle_beta                 124.251(8)
_cell_angle_gamma                90.00
_cell_volume                     2582.5(5)
_cell_formula_units_Z            4
_cell_measurement_temperature    298(2)
_cell_measurement_reflns_used    8696
_cell_measurement_theta_min      1.81
_cell_measurement_theta_max      29.30

_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    2.124
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1560
_exptl_absorpt_coefficient_mu    9.291
_exptl_absorpt_correction_type   numerical
_exptl_absorpt_correction_T_min  0.5102
_exptl_absorpt_correction_T_max  0.6891
_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            8696
_diffrn_reflns_av_R_equivalents  0.0984
_diffrn_reflns_av_sigmaI/netI    0.1166
_diffrn_reflns_limit_h_min       -22
_diffrn_reflns_limit_h_max       31
_diffrn_reflns_limit_k_min       -5
_diffrn_reflns_limit_k_max       6
_diffrn_reflns_limit_l_min       -37
_diffrn_reflns_limit_l_max       37
_diffrn_reflns_theta_min         1.81
_diffrn_reflns_theta_max         29.30
_reflns_number_total             3466
_reflns_number_gt                2335
_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)+(0.1012P)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         3466
_refine_ls_number_parameters     159
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1017
_refine_ls_R_factor_gt           0.0701
_refine_ls_wR_factor_ref         0.1853
_refine_ls_wR_factor_gt          0.1680
_refine_ls_goodness_of_fit_ref   0.971
_refine_ls_restrained_S_all      0.971
_refine_ls_shift/su_max          0.003
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C -0.1009(6) -0.382(2) 0.1326(3) 0.044(2) Uani 1 1 d . . .
H1 H -0.0736 -0.2946 0.1224 0.053 Uiso 1 1 calc R . .
C2 C -0.1368(7) -0.428(3) 0.1947(5) 0.053(3) Uani 1 1 d . . .
H2 H -0.1356 -0.3682 0.2276 0.063 Uiso 1 1 calc R . .
C3 C -0.1810(6) -0.630(3) 0.1614(5) 0.055(3) Uani 1 1 d . . .
H3 H -0.2077 -0.7134 0.1727 0.066 Uiso 1 1 calc R . .
C4 C -0.1865(6) -0.712(2) 0.1105(4) 0.049(3) Uani 1 1 d . . .
H4 H -0.2167 -0.8505 0.0869 0.059 Uiso 1 1 calc R . .
C5 C -0.1456(6) -0.580(2) 0.0957(4) 0.040(2) Uani 1 1 d . . .
C6 C -0.1470(6) -0.675(2) 0.0423(4) 0.043(2) Uani 1 1 d . . .
C7 C -0.1273(7) -0.526(2) -0.0327(5) 0.050(3) Uani 1 1 d . . .
C8 C -0.1664(6) -0.376(3) -0.0843(4) 0.049(3) Uani 1 1 d . . .
H8 H -0.1974 -0.2451 -0.0881 0.059 Uiso 1 1 calc R . .
C9 C -0.1587(7) -0.425(3) -0.1297(5) 0.057(3) Uani 1 1 d . . .
C10 C -0.1132(9) -0.618(3) -0.1253(6) 0.074(4) Uani 1 1 d . . .
H10 H -0.1086 -0.6502 -0.1566 0.089 Uiso 1 1 calc R . .
C11 C -0.0753(10) -0.759(4) -0.0742(8) 0.090(5) Uani 1 1 d . . .
H11 H -0.0429 -0.8848 -0.0697 0.108 Uiso 1 1 calc R . .
C12 C -0.0836(8) -0.719(3) -0.0276(6) 0.073(4) Uani 1 1 d . . .
H12 H -0.0592 -0.8259 0.0064 0.088 Uiso 1 1 calc R . .
N1 N -0.0945(4) -0.3088(17) 0.1823(3) 0.0385(17) Uani 1 1 d . . .
N2 N -0.1384(6) -0.4733(18) 0.0135(4) 0.050(2) Uani 1 1 d . . .
H2A H -0.1395 -0.3076 0.0229 0.060 Uiso 1 1 calc R . .
O1 O -0.1579(5) -0.9103(17) 0.0265(3) 0.058(2) Uani 1 1 d . . .
Hg1 Hg 0.0000 0.00851(13) 0.2500 0.0416(2) Uani 1 2 d S . .
Br1 Br 0.03516(6) 0.1240(3) 0.18230(4) 0.0542(3) Uani 1 1 d . . .
Cl1 Cl -0.2076(2) -0.2397(10) -0.19482(12) 0.0834(12) Uani 1 1 d . . .

loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_23
_atom_site_aniso_U_13
_atom_site_aniso_U_12
C1 0.053(6) 0.042(6) 0.026(3) 0.002(4) 0.014(4) 0.005(5)
C2 0.056(7) 0.058(7) 0.041(5) -0.003(5) 0.026(5) -0.007(6)
C3 0.047(6) 0.070(8) 0.049(5) 0.004(6) 0.027(5) -0.006(7)
C4 0.045(6) 0.039(6) 0.043(4) -0.001(4) 0.012(4) 0.002(5)
C5 0.043(5) 0.029(4) 0.038(4) 0.006(4) 0.018(4) 0.001(4)
C6 0.053(6) 0.025(4) 0.035(4) -0.006(3) 0.015(4) -0.005(4)
C7 0.068(7) 0.037(6) 0.045(5) -0.011(4) 0.032(5) -0.013(5)
C8 0.060(6) 0.050(7) 0.034(4) -0.004(4) 0.024(4) 0.008(6)
C9 0.064(7) 0.066(8) 0.047(5) -0.010(5) 0.035(5) -0.014(6)
C10 0.109(12) 0.060(9) 0.072(8) -0.009(7) 0.062(9) -0.008(10)
C11 0.118(14) 0.067(10) 0.114(12) 0.005(9) 0.084(12) 0.034(11)
C12 0.087(10) 0.065(9) 0.071(8) 0.015(7) 0.047(8) 0.025(8)
N1 0.038(4) 0.038(4) 0.030(3) -0.001(3) 0.014(3) 0.002(4)
N2 0.079(7) 0.032(5) 0.036(4) -0.003(3) 0.031(4) -0.002(4)
O1 0.082(6) 0.029(3) 0.053(4) -0.006(3) 0.032(4) -0.009(4)
Hg1 0.0446(3) 0.0458(3) 0.0287(2) 0.000 0.01713(19) 0.000
Br1 0.0609(7) 0.0623(8) 0.0442(5) -0.0002(5) 0.0325(5) -0.0088(6)
Cl1 0.084(2) 0.123(4) 0.0450(13) 0.0122(17) 0.0372(15) 0.006(2)

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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
C1 N1 1.329(11) . ?
C1 C5 1.366(15) . ?
C1 H1 0.9300 . ?
C2 N1 1.340(14) . ?
C2 C3 1.349(18) . ?
C2 H2 0.9300 . ?
C3 C4 1.382(15) . ?
C3 H3 0.9300 . ?
C4 C5 1.386(15) . ?
C4 H4 0.9300 . ?
C5 C6 1.511(14) . ?
C6 O1 1.212(13) . ?
C6 N2 1.350(13) . ?
C7 C12 1.341(18) . ?
C7 C8 1.381(15) . ?
C7 N2 1.446(14) . ?
C8 C9 1.370(14) . ?
C8 H8 0.9300 . ?
C9 C10 1.38(2) . ?
C9 Cl1 1.734(13) . ?
C10 C11 1.35(2) . ?
C10 H10 0.9300 . ?
C11 C12 1.402(19) . ?
C11 H11 0.9300 . ?
C12 H12 0.9300 . ?
N1 Hg1 2.473(8) . ?
N2 H2A 0.8600 . ?
Hg1 Br1 2.4709(10) 2 ?
Hg1 Br1 2.4710(10) . ?
Hg1 N1 2.473(8) 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 C5 123.3(10) . . ?
N1 C1 H1 118.3 . . ?
C5 C1 H1 118.3 . . ?
N1 C2 C3 122.8(10) . . ?
N1 C2 H2 118.6 . . ?
C3 C2 H2 118.6 . . ?
C2 C3 C4 119.7(11) . . ?
C2 C3 H3 120.1 . . ?
C4 C3 H3 120.1 . . ?
C3 C4 C5 117.8(10) . . ?
C3 C4 H4 121.1 . . ?
C5 C4 H4 121.1 . . ?
C1 C5 C4 118.6(9) . . ?
C1 C5 C6 121.8(10) . . ?
C4 C5 C6 119.4(9) . . ?
O1 C6 N2 124.4(9) . . ?
O1 C6 C5 121.6(10) . . ?
N2 C6 C5 113.9(8) . . ?
C12 C7 C8 120.7(11) . . ?
C12 C7 N2 122.2(11) . . ?
C8 C7 N2 117.0(11) . . ?
C9 C8 C7 118.9(12) . . ?
C9 C8 H8 120.6 . . ?
C7 C8 H8 120.6 . . ?
C8 C9 C10 121.9(12) . . ?
C8 C9 Cl1 119.4(11) . . ?
C10 C9 Cl1 118.7(9) . . ?
C11 C10 C9 117.7(12) . . ?
C11 C10 H10 121.1 . . ?
C9 C10 H10 121.1 . . ?
C10 C11 C12 121.7(14) . . ?
C10 C11 H11 119.2 . . ?
C12 C11 H11 119.2 . . ?
C7 C12 C11 119.1(13) . . ?
C7 C12 H12 120.5 . . ?
C11 C12 H12 120.5 . . ?
C1 N1 C2 117.5(9) . . ?
C1 N1 Hg1 118.5(7) . . ?
C2 N1 Hg1 123.8(6) . . ?
C6 N2 C7 122.3(9) . . ?
C6 N2 H2A 118.8 . . ?
C7 N2 H2A 118.8 . . ?
Br1 Hg1 Br1 153.40(7) 2 . ?
Br1 Hg1 N1 96.67(17) 2 2 ?
Br1 Hg1 N1 100.04(18) . 2 ?
Br1 Hg1 N1 100.04(18) 2 . ?
Br1 Hg1 N1 96.67(17) . . ?
N1 Hg1 N1 101.7(4) 2 . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
N1 C2 C3 C4 -3(2) . . . . ?
C2 C3 C4 C5 0.1(19) . . . . ?
N1 C1 C5 C4 0.1(17) . . . . ?
N1 C1 C5 C6 -174.7(9) . . . . ?
C3 C4 C5 C1 1.5(16) . . . . ?
C3 C4 C5 C6 176.5(10) . . . . ?
C1 C5 C6 O1 144.4(12) . . . . ?
C4 C5 C6 O1 -30.5(16) . . . . ?
C1 C5 C6 N2 -38.4(15) . . . . ?
C4 C5 C6 N2 146.7(10) . . . . ?
C12 C7 C8 C9 -1.4(19) . . . . ?
N2 C7 C8 C9 -178.4(11) . . . . ?
C7 C8 C9 C10 0(2) . . . . ?
C7 C8 C9 Cl1 179.8(10) . . . . ?
C8 C9 C10 C11 -1(2) . . . . ?
Cl1 C9 C10 C11 179.6(13) . . . . ?
C9 C10 C11 C12 3(3) . . . . ?
C8 C7 C12 C11 3(2) . . . . ?
N2 C7 C12 C11 -179.9(14) . . . . ?
C10 C11 C12 C7 -4(3) . . . . ?
C5 C1 N1 C2 -3.3(16) . . . . ?
C5 C1 N1 Hg1 171.8(8) . . . . ?
C3 C2 N1 C1 5.0(18) . . . . ?
C3 C2 N1 Hg1 -169.9(10) . . . . ?
O1 C6 N2 C7 -13(2) . . . . ?
C5 C6 N2 C7 170.1(10) . . . . ?
C12 C7 N2 C6 -43.9(19) . . . . ?
C8 C7 N2 C6 133.0(12) . . . . ?
C1 N1 Hg1 Br1 168.6(7) . . . 2 ?
C2 N1 Hg1 Br1 -16.6(9) . . . 2 ?
C1 N1 Hg1 Br1 9.4(7) . . . . ?
C2 N1 Hg1 Br1 -175.8(9) . . . . ?
C1 N1 Hg1 N1 -92.4(8) . . . 2 ?
C2 N1 Hg1 N1 82.5(9) . . . 2 ?

_diffrn_measured_fraction_theta_max 0.979
_diffrn_reflns_theta_full        29.30
_diffrn_measured_fraction_theta_full 0.979
_refine_diff_density_max         1.581
_refine_diff_density_min         -1.601
_refine_diff_density_rms         0.287
####################################################################### 
# 
# 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\908\kh908-new
_database_code_depnum_ccdc_archive 'CCDC 1016677'
_audit_update_record             
;
2014-07-28 deposited with the CCDC.	2024-01-03 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C24 H18 Cl2 Hg3 I6 N4 O2'
_chemical_formula_weight         1828.49

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'
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                   4.5347(4)
_cell_length_b                   21.3006(12)
_cell_length_c                   19.0448(15)
_cell_angle_alpha                90.00
_cell_angle_beta                 91.533(7)
_cell_angle_gamma                90.00
_cell_volume                     1838.9(2)
_cell_formula_units_Z            2
_cell_measurement_temperature    298(2)
_cell_measurement_reflns_used    20271
_cell_measurement_theta_min      1.91
_cell_measurement_theta_max      29.25

_exptl_crystal_description       Needle
_exptl_crystal_colour            Colorless
_exptl_crystal_size_max          0.30
_exptl_crystal_size_mid          0.07
_exptl_crystal_size_min          0.06
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    3.302
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1596
_exptl_absorpt_coefficient_mu    17.703
_exptl_absorpt_correction_type   numerical
_exptl_absorpt_correction_T_min  0.1152
_exptl_absorpt_correction_T_max  0.6787
_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            20271
_diffrn_reflns_av_R_equivalents  0.0915
_diffrn_reflns_av_sigmaI/netI    0.0987
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_k_min       -26
_diffrn_reflns_limit_k_max       29
_diffrn_reflns_limit_l_min       -26
_diffrn_reflns_limit_l_max       25
_diffrn_reflns_theta_min         1.91
_diffrn_reflns_theta_max         29.25
_reflns_number_total             4955
_reflns_number_gt                3737
_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)+(0.0250P)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         4955
_refine_ls_number_parameters     182
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.915
_refine_ls_R_factor_gt           0.0906
_refine_ls_wR_factor_ref         0.1419
_refine_ls_wR_factor_gt          0.1101
_refine_ls_goodness_of_fit_ref   0.939
_refine_ls_restrained_S_all      0.939
_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 0.544(4) 0.1559(10) 0.6792(12) 0.044(5) Uani 1 1 d . . .
H1 H 0.6838 0.1246 0.6871 0.053 Uiso 1 1 calc R . .
C2 C 0.274(5) 0.2364(12) 0.7198(12) 0.056(6) Uani 1 1 d . . .
H2 H 0.2164 0.2611 0.7573 0.068 Uiso 1 1 calc R . .
C3 C 0.178(5) 0.2527(10) 0.6541(11) 0.051(6) Uani 1 1 d . . .
H3 H 0.0492 0.2862 0.6471 0.061 Uiso 1 1 calc R . .
C4 C 0.277(4) 0.2184(11) 0.5980(12) 0.048(6) Uani 1 1 d . . .
H4 H 0.2241 0.2302 0.5524 0.058 Uiso 1 1 calc R . .
C5 C 0.455(3) 0.1667(9) 0.6095(10) 0.027(4) Uani 1 1 d . . .
C6 C 0.580(4) 0.1269(9) 0.5530(10) 0.030(4) Uani 1 1 d . . .
C7 C 0.469(3) 0.0902(9) 0.4329(10) 0.036(4) Uani 1 1 d . . .
C8 C 0.331(4) 0.1110(10) 0.3737(10) 0.042(5) Uani 1 1 d . . .
H8 H 0.1951 0.1436 0.3765 0.050 Uiso 1 1 calc R . .
C9 C 0.389(4) 0.0848(11) 0.3086(11) 0.050(7) Uani 1 1 d . . .
C10 C 0.585(4) 0.0367(12) 0.3049(13) 0.052(7) Uani 1 1 d . . .
H10 H 0.6268 0.0189 0.2617 0.063 Uiso 1 1 calc R . .
C11 C 0.721(5) 0.0149(11) 0.3643(13) 0.050(6) Uani 1 1 d . . .
H11 H 0.8547 -0.0181 0.3620 0.060 Uiso 1 1 calc R . .
C12 C 0.660(4) 0.0411(11) 0.4271(10) 0.041(6) Uani 1 1 d . . .
H12 H 0.7523 0.0252 0.4675 0.050 Uiso 1 1 calc R . .
N1 N 0.451(3) 0.1850(8) 0.7337(9) 0.042(4) Uani 1 1 d . . .
N2 N 0.395(3) 0.1184(8) 0.4961(10) 0.044(5) Uani 1 1 d . . .
H2A H 0.2169 0.1318 0.4994 0.053 Uiso 1 1 calc R . .
O1 O 0.833(3) 0.1088(7) 0.5576(7) 0.049(4) Uani 1 1 d . . .
Hg1 Hg 0.55843(19) 0.15510(5) 0.85619(5) 0.0515(3) Uani 1 1 d . . .
Hg2 Hg 0.0000 0.0000 1.0000 0.0746(5) Uani 1 2 d S . .
I1 I 0.2523(3) 0.23794(8) 0.92529(8) 0.0498(4) Uani 1 1 d . . .
I2 I 0.9381(3) 0.06477(7) 0.83141(8) 0.0437(4) Uani 1 1 d . . .
I3 I -0.3429(4) 0.08496(9) 1.05106(9) 0.0670(5) Uani 1 1 d . . .
Cl1 Cl 0.2119(15) 0.1164(3) 0.2338(3) 0.0715(19) Uani 1 1 d . . .

loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_23
_atom_site_aniso_U_13
_atom_site_aniso_U_12
C1 0.076(11) 0.040(12) 0.037(15) -0.005(13) 0.009(10) 0.011(10)
C2 0.075(15) 0.060(18) 0.035(14) 0.002(14) 0.004(11) 0.007(13)
C3 0.090(16) 0.035(14) 0.028(12) 0.012(11) 0.007(11) 0.022(12)
C4 0.050(12) 0.052(16) 0.044(14) 0.020(13) 0.006(10) 0.005(11)
C5 0.024(9) 0.031(12) 0.025(11) -0.009(9) 0.010(8) -0.012(8)
C6 0.041(10) 0.034(12) 0.025(11) 0.019(9) 0.008(8) -0.008(8)
C7 0.048(10) 0.034(12) 0.029(11) 0.009(9) 0.010(8) -0.009(8)
C8 0.060(13) 0.034(13) 0.034(12) -0.001(10) 0.010(10) 0.014(10)
C9 0.054(12) 0.044(16) 0.045(14) -0.011(13) 0.013(10) -0.018(11)
C10 0.030(11) 0.072(18) 0.056(16) -0.020(14) 0.012(11) -0.009(11)
C11 0.057(13) 0.046(15) 0.048(15) -0.012(13) 0.007(12) -0.010(11)
C12 0.057(11) 0.047(17) 0.042(11) 0.002(11) -0.007(9) 0.010(10)
N1 0.058(11) 0.039(11) 0.030(10) 0.011(9) -0.010(8) -0.007(9)
N2 0.041(8) 0.042(11) 0.029(14) 0.011(10) 0.009(8) 0.014(7)
O1 0.028(7) 0.077(12) 0.044(9) -0.015(9) 0.003(6) 0.013(7)
Hg1 0.0631(6) 0.0487(6) 0.0430(5) -0.0012(6) 0.0097(4) 0.0223(5)
Hg2 0.0859(10) 0.0664(12) 0.0723(11) 0.0008(9) 0.0206(8) 0.0342(8)
I1 0.0495(8) 0.0482(10) 0.0520(9) -0.0136(8) 0.0064(7) 0.0096(7)
I2 0.0448(8) 0.0417(9) 0.0447(9) -0.0060(8) 0.0011(6) 0.0114(6)
I3 0.0794(11) 0.0567(12) 0.0654(12) -0.0092(10) 0.0100(9) 0.0243(8)
Cl1 0.100(5) 0.075(5) 0.039(4) -0.002(4) -0.001(3) -0.003(4)

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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
C1 N1 1.29(2) . ?
C1 C5 1.40(3) . ?
C1 H1 0.9300 . ?
C2 C3 1.36(3) . ?
C2 N1 1.38(3) . ?
C2 H2 0.9300 . ?
C3 C4 1.38(3) . ?
C3 H3 0.9300 . ?
C4 C5 1.38(3) . ?
C4 H4 0.9300 . ?
C5 C6 1.49(3) . ?
C6 O1 1.214(19) . ?
C6 N2 1.36(2) . ?
C7 C8 1.35(3) . ?
C7 C12 1.37(3) . ?
C7 N2 1.39(2) . ?
C8 C9 1.39(2) . ?
C8 H8 0.9300 . ?
C9 C10 1.36(3) . ?
C9 Cl1 1.75(3) . ?
C10 C11 1.36(3) . ?
C10 H10 0.9300 . ?
C11 C12 1.35(3) . ?
C11 H11 0.9300 . ?
C12 H12 0.9300 . ?
N1 Hg1 2.454(17) . ?
N2 H2A 0.8600 . ?
Hg1 I1 2.6211(17) . ?
Hg1 I2 2.6329(16) . ?
Hg2 I3 2.5920(15) . ?
Hg2 I3 2.5920(15) 3_557 ?

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 C5 126.5(19) . . ?
N1 C1 H1 116.7 . . ?
C5 C1 H1 116.7 . . ?
C3 C2 N1 123(2) . . ?
C3 C2 H2 118.3 . . ?
N1 C2 H2 118.3 . . ?
C2 C3 C4 118(2) . . ?
C2 C3 H3 120.8 . . ?
C4 C3 H3 120.8 . . ?
C3 C4 C5 120(2) . . ?
C3 C4 H4 119.9 . . ?
C5 C4 H4 119.9 . . ?
C4 C5 C1 115.7(18) . . ?
C4 C5 C6 124.9(18) . . ?
C1 C5 C6 119.1(17) . . ?
O1 C6 N2 125.1(17) . . ?
O1 C6 C5 120.4(17) . . ?
N2 C6 C5 114.3(16) . . ?
C8 C7 C12 117.8(18) . . ?
C8 C7 N2 117.5(16) . . ?
C12 C7 N2 124.6(18) . . ?
C7 C8 C9 121.2(19) . . ?
C7 C8 H8 119.4 . . ?
C9 C8 H8 119.4 . . ?
C10 C9 C8 119(2) . . ?
C10 C9 Cl1 122.3(17) . . ?
C8 C9 Cl1 118.5(18) . . ?
C11 C10 C9 120(2) . . ?
C11 C10 H10 120.1 . . ?
C9 C10 H10 120.1 . . ?
C12 C11 C10 120(2) . . ?
C12 C11 H11 120.1 . . ?
C10 C11 H11 120.1 . . ?
C11 C12 C7 122(2) . . ?
C11 C12 H12 118.9 . . ?
C7 C12 H12 118.9 . . ?
C1 N1 C2 115.2(18) . . ?
C1 N1 Hg1 125.5(15) . . ?
C2 N1 Hg1 119.2(14) . . ?
C6 N2 C7 126.0(15) . . ?
C6 N2 H2A 117.0 . . ?
C7 N2 H2A 117.0 . . ?
N1 Hg1 I1 102.0(4) . . ?
N1 Hg1 I2 97.6(4) . . ?
I1 Hg1 I2 159.98(6) . . ?
I3 Hg2 I3 179.998(1) . 3_557 ?

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 C2 C3 C4 -4(4) . . . . ?
C2 C3 C4 C5 4(3) . . . . ?
C3 C4 C5 C1 -5(3) . . . . ?
C3 C4 C5 C6 -178.8(18) . . . . ?
N1 C1 C5 C4 8(3) . . . . ?
N1 C1 C5 C6 -178.1(18) . . . . ?
C4 C5 C6 O1 138(2) . . . . ?
C1 C5 C6 O1 -35(2) . . . . ?
C4 C5 C6 N2 -37(2) . . . . ?
C1 C5 C6 N2 150.0(17) . . . . ?
C12 C7 C8 C9 -2(3) . . . . ?
N2 C7 C8 C9 -179.2(17) . . . . ?
C7 C8 C9 C10 1(3) . . . . ?
C7 C8 C9 Cl1 -177.7(15) . . . . ?
C8 C9 C10 C11 0(3) . . . . ?
Cl1 C9 C10 C11 178.7(16) . . . . ?
C9 C10 C11 C12 0(3) . . . . ?
C10 C11 C12 C7 -1(3) . . . . ?
C8 C7 C12 C11 2(3) . . . . ?
N2 C7 C12 C11 179.1(18) . . . . ?
C5 C1 N1 C2 -8(3) . . . . ?
C5 C1 N1 Hg1 170.8(14) . . . . ?
C3 C2 N1 C1 6(3) . . . . ?
C3 C2 N1 Hg1 -173.2(17) . . . . ?
O1 C6 N2 C7 -3(3) . . . . ?
C5 C6 N2 C7 171.5(16) . . . . ?
C8 C7 N2 C6 -148.1(19) . . . . ?
C12 C7 N2 C6 35(3) . . . . ?
C1 N1 Hg1 I1 -177.0(15) . . . . ?
C2 N1 Hg1 I1 1.9(16) . . . . ?
C1 N1 Hg1 I2 6.7(16) . . . . ?
C2 N1 Hg1 I2 -174.4(15) . . . . ?

_diffrn_measured_fraction_theta_max 0.991
_diffrn_reflns_theta_full        29.25
_diffrn_measured_fraction_theta_full 0.991
_refine_diff_density_max         1.012
_refine_diff_density_min         -1.049
_refine_diff_density_rms         0.291
####################################################################### 
# 
# 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\d123\khd123-abs
_audit_block_doi                 10.5517/ccdc.csd.cc1345m1
_database_code_depnum_ccdc_archive 'CCDC 1016912'
loop_
_citation_id
_citation_doi
_citation_year
1 10.1021/acs.cgd.9b01385 2020
loop_
_audit_author_name
_audit_author_address
'Hamid Reza Khavasi'
;Shahid Beheshti University
Iran
;
_audit_update_record             
;
2014-07-29 deposited with the CCDC.	2024-01-03 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C20 H18 Hg2 I6 N8 O4'
_chemical_formula_weight         1597.00

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

_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                   8.0015(12)
_cell_length_b                   9.2079(13)
_cell_length_c                   12.4641(18)
_cell_angle_alpha                98.279(12)
_cell_angle_beta                 100.092(12)
_cell_angle_gamma                108.027(11)
_cell_volume                     840.2(2)
_cell_formula_units_Z            1
_cell_measurement_temperature    298(2)
_cell_measurement_reflns_used    8842
_cell_measurement_theta_min      2.38
_cell_measurement_theta_max      29.16

_exptl_crystal_description       Block
_exptl_crystal_colour            Yellow
_exptl_crystal_size_max          0.50
_exptl_crystal_size_mid          0.48
_exptl_crystal_size_min          0.46
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    3.156
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             704
_exptl_absorpt_coefficient_mu    14.676
_exptl_absorpt_correction_type   numerical
_exptl_absorpt_correction_T_min  0.0125
_exptl_absorpt_correction_T_max  0.0764
_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            8842
_diffrn_reflns_av_R_equivalents  0.0860
_diffrn_reflns_av_sigmaI/netI    0.0843
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_theta_min         2.38
_diffrn_reflns_theta_max         29.16
_reflns_number_total             4470
_reflns_number_gt                2980
_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)+(0.1063P)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     SHELXL
_refine_ls_extinction_coef       0.0082(8)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_number_reflns         4470
_refine_ls_number_parameters     182
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0857
_refine_ls_R_factor_gt           0.0627
_refine_ls_wR_factor_ref         0.1713
_refine_ls_wR_factor_gt          0.1611
_refine_ls_goodness_of_fit_ref   0.926
_refine_ls_restrained_S_all      0.926
_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 0.7270(17) 0.8142(14) 0.3059(10) 0.047(3) Uani 1 1 d . . .
H1 H 0.7820 0.8297 0.3808 0.057 Uiso 1 1 calc R . .
C2 C 0.7941(19) 0.9228(14) 0.2473(10) 0.052(3) Uani 1 1 d . . .
H2 H 0.8919 1.0120 0.2840 0.062 Uiso 1 1 calc R . .
C3 C 0.5791(18) 0.7793(13) 0.0926(9) 0.046(3) Uani 1 1 d . . .
H3 H 0.5215 0.7657 0.0184 0.055 Uiso 1 1 calc R . .
C4 C 0.5094(16) 0.6660(12) 0.1511(8) 0.040(2) Uani 1 1 d . . .
C5 C 0.3429(18) 0.5282(14) 0.0982(9) 0.047(3) Uani 1 1 d . . .
C6 C 0.1037(18) 0.8305(13) 0.0694(10) 0.048(3) Uani 1 1 d . . .
C7 C 0.2487(19) 0.9555(14) 0.1442(11) 0.054(3) Uani 1 1 d . . .
H7 H 0.3137 1.0403 0.1183 0.065 Uiso 1 1 calc R . .
C8 C 0.2922(18) 0.9503(15) 0.2546(11) 0.055(3) Uani 1 1 d . . .
H8 H 0.3859 1.0319 0.3042 0.066 Uiso 1 1 calc R . .
C9 C 0.1932(16) 0.8195(14) 0.2924(10) 0.046(2) Uani 1 1 d . . .
C10 C 0.0598(16) 0.7022(13) 0.2194(10) 0.047(3) Uani 1 1 d . . .
H10 H -0.0044 0.6153 0.2436 0.057 Uiso 1 1 calc R . .
N1 N 0.5830(14) 0.6847(10) 0.2586(7) 0.0406(19) Uani 1 1 d . . .
N2 N 0.7241(16) 0.9065(12) 0.1375(9) 0.053(2) Uani 1 1 d . . .
N3 N 0.0174(13) 0.7092(11) 0.1101(8) 0.045(2) Uani 1 1 d . . .
H3A H -0.0687 0.6321 0.0651 0.054 Uiso 1 1 calc R . .
N4 N 0.0525(17) 0.8286(14) -0.0384(9) 0.059(3) Uani 1 1 d . . .
H4B H -0.0349 0.7500 -0.0809 0.071 Uiso 1 1 calc R . .
H4A H 0.1069 0.9058 -0.0656 0.071 Uiso 1 1 calc R . .
O1 O 0.2893(14) 0.4221(12) 0.1488(8) 0.067(3) Uani 1 1 d . . .
O2 O 0.2687(15) 0.5284(12) 0.0002(8) 0.072(3) Uani 1 1 d . . .
I1 I 0.24507(13) 0.80563(11) 0.46032(7) 0.0607(3) Uani 1 1 d . . .
I2 I 0.71336(11) 0.30713(9) 0.25572(7) 0.0513(2) Uani 1 1 d . . .
I3 I 0.22632(11) 0.34113(11) 0.42900(7) 0.0567(3) Uani 1 1 d . . .
Hg1 Hg 0.49750(7) 0.44446(6) 0.33219(4) 0.0543(2) Uani 1 1 d . . .

loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_23
_atom_site_aniso_U_13
_atom_site_aniso_U_12
C1 0.056(7) 0.035(6) 0.043(5) 0.011(4) 0.006(5) 0.009(5)
C2 0.059(7) 0.034(6) 0.049(6) 0.006(5) 0.006(5) 0.002(5)
C3 0.062(7) 0.030(5) 0.039(5) 0.010(4) 0.009(5) 0.008(5)
C4 0.055(6) 0.026(5) 0.039(5) 0.003(4) 0.013(5) 0.018(5)
C5 0.061(7) 0.037(6) 0.043(5) 0.011(4) 0.015(5) 0.014(5)
C6 0.057(7) 0.027(5) 0.057(6) 0.006(4) 0.019(5) 0.007(5)
C7 0.062(8) 0.032(6) 0.061(7) 0.015(5) 0.019(6) 0.000(5)
C8 0.050(7) 0.037(6) 0.055(7) 0.004(5) 0.004(5) -0.010(5)
C9 0.043(6) 0.038(6) 0.049(6) 0.011(5) 0.008(5) 0.003(4)
C10 0.048(6) 0.026(5) 0.062(7) 0.015(5) 0.021(5) -0.001(4)
N1 0.052(5) 0.031(4) 0.037(4) 0.008(3) 0.011(4) 0.011(4)
N2 0.063(7) 0.032(5) 0.056(6) 0.008(4) 0.013(5) 0.005(4)
N3 0.043(5) 0.034(5) 0.049(5) 0.007(4) 0.010(4) 0.002(4)
N4 0.071(7) 0.046(6) 0.055(6) 0.015(5) 0.015(5) 0.012(5)
O1 0.053(5) 0.067(6) 0.054(5) 0.026(4) -0.006(4) -0.013(5)
O2 0.076(7) 0.058(6) 0.045(4) 0.016(4) -0.013(4) -0.016(5)
I1 0.0622(5) 0.0583(5) 0.0508(4) 0.0156(4) 0.0089(4) 0.0061(4)
I2 0.0532(5) 0.0414(4) 0.0597(5) 0.0134(3) 0.0208(4) 0.0113(3)
I3 0.0462(4) 0.0605(5) 0.0492(4) 0.0099(3) 0.0145(3) -0.0025(3)
Hg1 0.0587(3) 0.0579(3) 0.0531(3) 0.0222(2) 0.0229(2) 0.0195(2)

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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
C1 N1 1.343(15) . ?
C1 C2 1.356(17) . ?
C1 H1 0.9300 . ?
C2 N2 1.352(17) . ?
C2 H2 0.9300 . ?
C3 N2 1.332(16) . ?
C3 C4 1.390(15) . ?
C3 H3 0.9300 . ?
C4 N1 1.329(14) . ?
C4 C5 1.492(16) . ?
C5 O1 1.245(14) . ?
C5 O2 1.261(15) . ?
C6 N4 1.330(17) . ?
C6 N3 1.338(15) . ?
C6 C7 1.423(17) . ?
C7 C8 1.370(19) . ?
C7 H7 0.9300 . ?
C8 C9 1.416(16) . ?
C8 H8 0.9300 . ?
C9 C10 1.340(16) . ?
C9 I1 2.091(12) . ?
C10 N3 1.361(16) . ?
C10 H10 0.9300 . ?
N1 Hg1 2.464(9) . ?
N3 H3A 0.8600 . ?
N4 H4B 0.8600 . ?
N4 H4A 0.8600 . ?
O1 Hg1 2.522(9) . ?
I2 Hg1 2.6593(10) . ?
I3 Hg1 2.6533(10) . ?
I3 Hg1 3.3080(12) 2_666 ?
Hg1 I3 3.3080(12) 2_666 ?

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(11) . . ?
N1 C1 H1 119.1 . . ?
C2 C1 H1 119.1 . . ?
N2 C2 C1 122.5(11) . . ?
N2 C2 H2 118.8 . . ?
C1 C2 H2 118.8 . . ?
N2 C3 C4 123.3(11) . . ?
N2 C3 H3 118.4 . . ?
C4 C3 H3 118.3 . . ?
N1 C4 C3 120.1(10) . . ?
N1 C4 C5 118.4(10) . . ?
C3 C4 C5 121.3(10) . . ?
O1 C5 O2 124.8(12) . . ?
O1 C5 C4 120.5(11) . . ?
O2 C5 C4 114.7(10) . . ?
N4 C6 N3 119.1(11) . . ?
N4 C6 C7 123.0(11) . . ?
N3 C6 C7 117.9(11) . . ?
C8 C7 C6 119.7(11) . . ?
C8 C7 H7 120.1 . . ?
C6 C7 H7 120.1 . . ?
C7 C8 C9 119.4(11) . . ?
C7 C8 H8 120.3 . . ?
C9 C8 H8 120.3 . . ?
C10 C9 C8 119.4(11) . . ?
C10 C9 I1 118.8(8) . . ?
C8 C9 I1 121.9(9) . . ?
C9 C10 N3 120.6(10) . . ?
C9 C10 H10 119.7 . . ?
N3 C10 H10 119.7 . . ?
C4 N1 C1 117.3(10) . . ?
C4 N1 Hg1 114.4(7) . . ?
C1 N1 Hg1 125.6(7) . . ?
C3 N2 C2 114.9(11) . . ?
C6 N3 C10 122.9(10) . . ?
C6 N3 H3A 118.5 . . ?
C10 N3 H3A 118.5 . . ?
C6 N4 H4B 120.0 . . ?
C6 N4 H4A 120.0 . . ?
H4B N4 H4A 120.0 . . ?
C5 O1 Hg1 115.5(8) . . ?
Hg1 I3 Hg1 87.54(3) . 2_666 ?
N1 Hg1 O1 67.4(3) . . ?
N1 Hg1 I3 127.9(2) . . ?
O1 Hg1 I3 93.2(2) . . ?
N1 Hg1 I2 99.9(2) . . ?
O1 Hg1 I2 98.7(3) . . ?
I3 Hg1 I2 131.48(4) . . ?
N1 Hg1 I3 86.3(2) . 2_666 ?
O1 Hg1 I3 150.2(3) . 2_666 ?
I3 Hg1 I3 92.46(3) . 2_666 ?
I2 Hg1 I3 99.33(3) . 2_666 ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
N1 C1 C2 N2 -2(2) . . . . ?
N2 C3 C4 N1 3.0(19) . . . . ?
N2 C3 C4 C5 177.9(11) . . . . ?
N1 C4 C5 O1 -10.1(18) . . . . ?
C3 C4 C5 O1 174.9(12) . . . . ?
N1 C4 C5 O2 171.8(12) . . . . ?
C3 C4 C5 O2 -3.2(17) . . . . ?
N4 C6 C7 C8 179.2(13) . . . . ?
N3 C6 C7 C8 -2(2) . . . . ?
C6 C7 C8 C9 1(2) . . . . ?
C7 C8 C9 C10 1(2) . . . . ?
C7 C8 C9 I1 -177.9(11) . . . . ?
C8 C9 C10 N3 -1(2) . . . . ?
I1 C9 C10 N3 177.7(9) . . . . ?
C3 C4 N1 C1 -1.3(16) . . . . ?
C5 C4 N1 C1 -176.4(10) . . . . ?
C3 C4 N1 Hg1 -164.0(9) . . . . ?
C5 C4 N1 Hg1 21.0(12) . . . . ?
C2 C1 N1 C4 0.7(18) . . . . ?
C2 C1 N1 Hg1 161.2(10) . . . . ?
C4 C3 N2 C2 -3.7(19) . . . . ?
C1 C2 N2 C3 3(2) . . . . ?
N4 C6 N3 C10 -179.4(12) . . . . ?
C7 C6 N3 C10 1.5(19) . . . . ?
C9 C10 N3 C6 -0.1(19) . . . . ?
O2 C5 O1 Hg1 171.5(11) . . . . ?
C4 C5 O1 Hg1 -6.4(16) . . . . ?
C4 N1 Hg1 O1 -16.8(8) . . . . ?
C1 N1 Hg1 O1 -177.8(10) . . . . ?
C4 N1 Hg1 I3 -92.4(7) . . . . ?
C1 N1 Hg1 I3 106.6(9) . . . . ?
C4 N1 Hg1 I2 78.5(8) . . . . ?
C1 N1 Hg1 I2 -82.5(9) . . . . ?
C4 N1 Hg1 I3 177.3(8) . . . 2_666 ?
C1 N1 Hg1 I3 16.4(9) . . . 2_666 ?
C5 O1 Hg1 N1 12.0(10) . . . . ?
C5 O1 Hg1 I3 142.0(10) . . . . ?
C5 O1 Hg1 I2 -85.2(10) . . . . ?
C5 O1 Hg1 I3 41.5(14) . . . 2_666 ?
Hg1 I3 Hg1 N1 -87.2(3) 2_666 . . . ?
Hg1 I3 Hg1 O1 -150.7(3) 2_666 . . . ?
Hg1 I3 Hg1 I2 104.75(4) 2_666 . . . ?
Hg1 I3 Hg1 I3 0.0 2_666 . . 2_666 ?

_diffrn_measured_fraction_theta_max 0.987
_diffrn_reflns_theta_full        29.16
_diffrn_measured_fraction_theta_full 0.987
_refine_diff_density_max         1.254
_refine_diff_density_min         -1.305
_refine_diff_density_rms         0.325
