# Electronic Supplementary Material (ESI) for CrystEngComm.
# This journal is © The Royal Society of Chemistry 2018

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

data_1
_database_code_depnum_ccdc_archive 'CCDC 1588625'
_audit_update_record             
;
2017-12-01 deposited with the CCDC.
2018-03-02 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C40 H36 Cl4 Hg2 N8 O4'
_chemical_formula_weight         1235.75

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

_space_group_crystal_system      orthorhombic
_space_group_IT_number           61
_space_group_name_H-M_alt        'P b c a'
_space_group_name_Hall           '-P 2ac 2ab'

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

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

_cell_length_a                   16.5711(7)
_cell_length_b                   14.2773(5)
_cell_length_c                   18.0085(7)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     4260.6(3)
_cell_formula_units_Z            4
_cell_measurement_temperature    299(2)
_cell_measurement_reflns_used    9917
_cell_measurement_theta_min      2.20
_cell_measurement_theta_max      28.30

_exptl_crystal_description       Block
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.926
_exptl_crystal_F_000             2368
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.400
_exptl_crystal_size_mid          0.400
_exptl_crystal_size_min          0.200
_exptl_absorpt_coefficient_mu    7.499
_shelx_estimated_absorpt_T_min   0.153
_shelx_estimated_absorpt_T_max   0.315
_exptl_absorpt_correction_type   multi_scan
_exptl_absorpt_correction_T_min  0.3736
_exptl_absorpt_correction_T_max  0.7457
_exptl_absorpt_process_details   'SADABS V2008/1 (Bruker AXS, 2008)'
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      299(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            23596
_diffrn_reflns_av_unetI/netI     0.0306
_diffrn_reflns_av_R_equivalents  0.0350
_diffrn_reflns_limit_h_min       -22
_diffrn_reflns_limit_h_max       22
_diffrn_reflns_limit_k_min       -19
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_l_min       -24
_diffrn_reflns_limit_l_max       23
_diffrn_reflns_theta_min         2.196
_diffrn_reflns_theta_max         28.310
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measured_fraction_theta_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_point_group_measured_fraction_full 1.000
_reflns_number_total             5289
_reflns_number_gt                4236
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

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

_computing_data_collection       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0378P)²+2.0394P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     'SHELXL-2014/7 (Sheldrick 2014'
_refine_ls_extinction_coef       0.00078(5)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_number_reflns         5289
_refine_ls_number_parameters     263
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0429
_refine_ls_R_factor_gt           0.0310
_refine_ls_wR_factor_ref         0.0750
_refine_ls_wR_factor_gt          0.0704
_refine_ls_goodness_of_fit_ref   1.042
_refine_ls_restrained_S_all      1.042
_refine_ls_shift/su_max          0.002
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Hg Hg 0.11402(2) 0.98746(2) 0.44402(2) 0.04218(7) Uani 1 1 d . . . . .
O1 O 0.31986(14) 0.7996(2) 0.28561(17) 0.0628(9) Uani 1 1 d . . . . .
O2 O 0.40708(13) 0.35127(17) 0.12240(15) 0.0433(6) Uani 1 1 d . . . . .
N1 N 0.25899(18) 1.0104(2) 0.42169(18) 0.0380(7) Uani 1 1 d . . . . .
N2 N 0.42261(15) 0.86056(19) 0.35187(15) 0.0339(6) Uani 1 1 d . . . . .
H2A H 0.4722 0.8526 0.3644 0.041 Uiso 1 1 calc R U . . .
N3 N 0.30947(17) 0.2692(2) 0.18006(17) 0.0450(8) Uani 1 1 d . . . . .
H3A H 0.2648 0.2725 0.2042 0.054 Uiso 1 1 calc R U . . .
N4 N 0.37691(17) 0.0664(2) 0.07061(16) 0.0376(7) Uani 1 1 d . . . . .
C1 C 0.3005(2) 1.0875(3) 0.4394(2) 0.0456(9) Uani 1 1 d . . . . .
H1A H 0.2727 1.1395 0.4572 0.055 Uiso 1 1 calc R U . . .
C2 C 0.3834(2) 1.0924(3) 0.4321(2) 0.0488(10) Uani 1 1 d . . . . .
H2B H 0.4110 1.1462 0.4462 0.059 Uiso 1 1 calc R U . . .
C3 C 0.4246(2) 1.0164(2) 0.4038(2) 0.0402(8) Uani 1 1 d . . . . .
H3B H 0.4804 1.0184 0.3984 0.048 Uiso 1 1 calc R U . . .
C4 C 0.38174(18) 0.9370(2) 0.38345(17) 0.0304(7) Uani 1 1 d . . . . .
C5 C 0.29839(19) 0.9364(2) 0.39435(18) 0.0345(7) Uani 1 1 d . . . . .
H5A H 0.2694 0.8828 0.3822 0.041 Uiso 1 1 calc R U . . .
C6 C 0.39062(18) 0.7984(2) 0.30338(19) 0.0350(7) Uani 1 1 d . . . . .
C7 C 0.45099(19) 0.7280(2) 0.2727(2) 0.0413(8) Uani 1 1 d . . . . .
H7A H 0.4975 0.7614 0.2536 0.050 Uiso 1 1 calc R U . . .
H7B H 0.4693 0.6877 0.3127 0.050 Uiso 1 1 calc R U . . .
C8 C 0.41545(18) 0.6684(2) 0.21164(19) 0.0334(7) Uani 1 1 d . . . . .
C9 C 0.38092(19) 0.5818(3) 0.2274(2) 0.0378(8) Uani 1 1 d . . . . .
H9A H 0.3814 0.5598 0.2760 0.045 Uiso 1 1 calc R U . . .
C10 C 0.3457(2) 0.5277(2) 0.1723(2) 0.0383(8) Uani 1 1 d . . . . .
C11 C 0.3454(2) 0.5615(3) 0.1008(2) 0.0459(9) Uani 1 1 d . . . . .
H11A H 0.3217 0.5264 0.0633 0.055 Uiso 1 1 calc R U . . .
C12 C 0.3796(2) 0.6462(3) 0.0842(2) 0.0496(10) Uani 1 1 d . . . . .
H12A H 0.3798 0.6677 0.0354 0.059 Uiso 1 1 calc R U . . .
C13 C 0.4137(2) 0.6999(3) 0.1396(2) 0.0414(8) Uani 1 1 d . . . . .
H13A H 0.4358 0.7580 0.1280 0.050 Uiso 1 1 calc R U . . .
C14 C 0.3055(2) 0.4363(3) 0.1917(3) 0.0528(10) Uani 1 1 d . . . . .
H14A H 0.2505 0.4378 0.1733 0.063 Uiso 1 1 calc R U . . .
H14B H 0.3029 0.4310 0.2453 0.063 Uiso 1 1 calc R U . . .
C15 C 0.34664(18) 0.3494(2) 0.16113(19) 0.0331(7) Uani 1 1 d . . . . .
C16 C 0.34037(19) 0.1795(2) 0.1622(2) 0.0372(7) Uani 1 1 d . . . . .
C17 C 0.3627(2) 0.1177(3) 0.2175(2) 0.0499(10) Uani 1 1 d . . . . .
H17A H 0.3572 0.1339 0.2673 0.060 Uiso 1 1 calc R U . . .
C18 C 0.3933(3) 0.0324(3) 0.1976(3) 0.0541(11) Uani 1 1 d . . . . .
H18A H 0.4098 -0.0095 0.2341 0.065 Uiso 1 1 calc R U . . .
C19 C 0.3995(2) 0.0084(3) 0.1251(2) 0.0424(9) Uani 1 1 d . . . . .
H19A H 0.4200 -0.0502 0.1128 0.051 Uiso 1 1 calc R U . . .
C20 C 0.3494(2) 0.1509(2) 0.0889(2) 0.0377(7) Uani 1 1 d . . . . .
H20A H 0.3358 0.1925 0.0511 0.045 Uiso 1 1 calc R U . . .
Cl1 Cl 0.07648(7) 1.14501(7) 0.46690(6) 0.0581(3) Uani 1 1 d . . . . .
Cl2 Cl 0.09934(6) 0.84878(8) 0.37329(7) 0.0600(3) Uani 1 1 d . . . . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Hg Cl2 2.3669(10) . ?
Hg Cl1 2.3699(10) . ?
Hg N4 2.410(3) 2_565 ?
Hg N1 2.458(3) . ?
O1 C6 1.216(4) . ?
O2 C15 1.221(4) . ?
N1 C5 1.336(4) . ?
N1 C1 1.337(5) . ?
N2 C6 1.354(4) . ?
N2 C4 1.405(4) . ?
N2 H2A 0.8600 . ?
N3 C15 1.344(4) . ?
N3 C16 1.416(4) . ?
N3 H3A 0.8600 . ?
N4 C20 1.332(4) . ?
N4 C19 1.337(5) . ?
N4 Hg 2.410(3) 2_564 ?
C1 C2 1.381(5) . ?
C1 H1A 0.9300 . ?
C2 C3 1.379(5) . ?
C2 H2B 0.9300 . ?
C3 C4 1.387(5) . ?
C3 H3B 0.9300 . ?
C4 C5 1.395(4) . ?
C5 H5A 0.9300 . ?
C6 C7 1.521(5) . ?
C7 C8 1.511(4) . ?
C7 H7A 0.9700 . ?
C7 H7B 0.9700 . ?
C8 C13 1.374(5) . ?
C8 C9 1.391(5) . ?
C9 C10 1.386(5) . ?
C9 H9A 0.9300 . ?
C10 C11 1.376(5) . ?
C10 C14 1.507(5) . ?
C11 C12 1.368(6) . ?
C11 H11A 0.9300 . ?
C12 C13 1.378(5) . ?
C12 H12A 0.9300 . ?
C13 H13A 0.9300 . ?
C14 C15 1.518(5) . ?
C14 H14A 0.9700 . ?
C14 H14B 0.9700 . ?
C16 C17 1.381(5) . ?
C16 C20 1.390(5) . ?
C17 C18 1.367(6) . ?
C17 H17A 0.9300 . ?
C18 C19 1.354(6) . ?
C18 H18A 0.9300 . ?
C19 H19A 0.9300 . ?
C20 H20A 0.9300 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
Cl2 Hg Cl1 149.38(4) . . ?
Cl2 Hg N4 104.40(8) . 2_565 ?
Cl1 Hg N4 98.89(8) . 2_565 ?
Cl2 Hg N1 97.11(7) . . ?
Cl1 Hg N1 99.13(7) . . ?
N4 Hg N1 97.83(10) 2_565 . ?
C5 N1 C1 119.2(3) . . ?
C5 N1 Hg 115.6(2) . . ?
C1 N1 Hg 125.0(2) . . ?
C6 N2 C4 125.6(3) . . ?
C6 N2 H2A 117.2 . . ?
C4 N2 H2A 117.2 . . ?
C15 N3 C16 123.2(3) . . ?
C15 N3 H3A 118.4 . . ?
C16 N3 H3A 118.4 . . ?
C20 N4 C19 118.4(3) . . ?
C20 N4 Hg 122.9(2) . 2_564 ?
C19 N4 Hg 118.6(3) . 2_564 ?
N1 C1 C2 122.0(4) . . ?
N1 C1 H1A 119.0 . . ?
C2 C1 H1A 119.0 . . ?
C3 C2 C1 119.2(4) . . ?
C3 C2 H2B 120.4 . . ?
C1 C2 H2B 120.4 . . ?
C2 C3 C4 119.1(3) . . ?
C2 C3 H3B 120.4 . . ?
C4 C3 H3B 120.4 . . ?
C3 C4 C5 118.3(3) . . ?
C3 C4 N2 119.7(3) . . ?
C5 C4 N2 122.0(3) . . ?
N1 C5 C4 122.0(3) . . ?
N1 C5 H5A 119.0 . . ?
C4 C5 H5A 119.0 . . ?
O1 C6 N2 122.6(3) . . ?
O1 C6 C7 123.3(3) . . ?
N2 C6 C7 114.2(3) . . ?
C8 C7 C6 112.3(3) . . ?
C8 C7 H7A 109.1 . . ?
C6 C7 H7A 109.1 . . ?
C8 C7 H7B 109.1 . . ?
C6 C7 H7B 109.1 . . ?
H7A C7 H7B 107.9 . . ?
C13 C8 C9 118.4(3) . . ?
C13 C8 C7 120.8(3) . . ?
C9 C8 C7 120.8(3) . . ?
C10 C9 C8 121.5(3) . . ?
C10 C9 H9A 119.3 . . ?
C8 C9 H9A 119.3 . . ?
C11 C10 C9 118.4(3) . . ?
C11 C10 C14 121.2(3) . . ?
C9 C10 C14 120.3(3) . . ?
C12 C11 C10 120.9(3) . . ?
C12 C11 H11A 119.6 . . ?
C10 C11 H11A 119.6 . . ?
C11 C12 C13 120.2(4) . . ?
C11 C12 H12A 119.9 . . ?
C13 C12 H12A 119.9 . . ?
C8 C13 C12 120.7(4) . . ?
C8 C13 H13A 119.7 . . ?
C12 C13 H13A 119.7 . . ?
C10 C14 C15 115.2(3) . . ?
C10 C14 H14A 108.5 . . ?
C15 C14 H14A 108.5 . . ?
C10 C14 H14B 108.5 . . ?
C15 C14 H14B 108.5 . . ?
H14A C14 H14B 107.5 . . ?
O2 C15 N3 122.6(3) . . ?
O2 C15 C14 123.9(3) . . ?
N3 C15 C14 113.5(3) . . ?
C17 C16 C20 117.9(3) . . ?
C17 C16 N3 120.7(3) . . ?
C20 C16 N3 121.4(3) . . ?
C18 C17 C16 118.7(4) . . ?
C18 C17 H17A 120.7 . . ?
C16 C17 H17A 120.7 . . ?
C19 C18 C17 120.4(4) . . ?
C19 C18 H18A 119.8 . . ?
C17 C18 H18A 119.8 . . ?
N4 C19 C18 122.0(4) . . ?
N4 C19 H19A 119.0 . . ?
C18 C19 H19A 119.0 . . ?
N4 C20 C16 122.5(3) . . ?
N4 C20 H20A 118.7 . . ?
C16 C20 H20A 118.7 . . ?

_refine_diff_density_max         1.304
_refine_diff_density_min         -1.005
_refine_diff_density_rms         0.104

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

data_5
_database_code_depnum_ccdc_archive 'CCDC 1588629'
_audit_update_record             
;
2017-12-01 deposited with the CCDC.
2018-03-02 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C22 H21 Hg I2 N5 O2'
_chemical_formula_weight         841.83

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'

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

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

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

_cell_length_a                   14.9250(5)
_cell_length_b                   17.9225(6)
_cell_length_c                   9.7074(3)
_cell_angle_alpha                90
_cell_angle_beta                 99.086(2)
_cell_angle_gamma                90
_cell_volume                     2564.08(15)
_cell_formula_units_Z            4
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    9847
_cell_measurement_theta_min      2.27
_cell_measurement_theta_max      28.02

_exptl_crystal_description       neddle
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    2.181
_exptl_crystal_F_000             1560
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.400
_exptl_crystal_size_mid          0.100
_exptl_crystal_size_min          0.050
_exptl_absorpt_coefficient_mu    8.438
_shelx_estimated_absorpt_T_min   0.133
_shelx_estimated_absorpt_T_max   0.678
_exptl_absorpt_correction_type   multi_scan
_exptl_absorpt_correction_T_min  0.4521
_exptl_absorpt_correction_T_max  0.7457
_exptl_absorpt_process_details   'sadabs v2008/1(bruker axs, 2008)'
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      296(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            24645
_diffrn_reflns_av_unetI/netI     0.0421
_diffrn_reflns_av_R_equivalents  0.0386
_diffrn_reflns_limit_h_min       -19
_diffrn_reflns_limit_h_max       18
_diffrn_reflns_limit_k_min       -23
_diffrn_reflns_limit_k_max       19
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_theta_min         1.382
_diffrn_reflns_theta_max         28.297
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.995
_diffrn_measured_fraction_theta_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.995
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.995
_diffrn_reflns_point_group_measured_fraction_full 1.000
_reflns_number_total             6330
_reflns_number_gt                4106
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

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

_computing_data_collection       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0503P)²+7.9216P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         6330
_refine_ls_number_parameters     289
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0825
_refine_ls_R_factor_gt           0.0448
_refine_ls_wR_factor_ref         0.1254
_refine_ls_wR_factor_gt          0.1121
_refine_ls_goodness_of_fit_ref   1.042
_refine_ls_restrained_S_all      1.042
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Hg Hg 0.64808(2) 0.91801(2) 0.35201(3) 0.06691(14) Uani 1 1 d . . . . .
I1 I 0.52608(5) 0.86553(6) 0.49187(7) 0.1163(4) Uani 1 1 d . . . . .
I2 I 0.76555(4) 1.02780(4) 0.34883(7) 0.0792(2) Uani 1 1 d . . . . .
O1 O 0.9050(4) 0.8953(3) 0.0331(7) 0.0738(16) Uani 1 1 d . . . . .
O2 O 1.3559(3) 0.7322(3) 0.2249(4) 0.0503(12) Uani 1 1 d . . . . .
N1 N 0.7313(5) 0.8081(4) 0.2867(8) 0.0658(18) Uani 1 1 d . . . . .
N2 N 0.9082(4) 0.7709(4) 0.0692(7) 0.0609(17) Uani 1 1 d . . . . .
H2A H 0.9353 0.7310 0.0489 0.073 Uiso 1 1 calc R U . . .
N3 N 1.3717(3) 0.7009(3) 0.4526(5) 0.0396(12) Uani 1 1 d . . . . .
H3A H 1.3481 0.7068 0.5272 0.048 Uiso 1 1 calc R U . . .
N4 N 1.5658(4) 0.5950(4) 0.6173(6) 0.0525(15) Uani 1 1 d . . . . .
C1 C 0.7065(6) 0.7395(6) 0.3115(10) 0.079(3) Uani 1 1 d . . . . .
H1A H 0.6624 0.7321 0.3679 0.095 Uiso 1 1 calc R U . . .
C2 C 0.7441(8) 0.6786(6) 0.2565(12) 0.088(3) Uani 1 1 d . . . . .
H2B H 0.7241 0.6308 0.2733 0.105 Uiso 1 1 calc R U . . .
C3 C 0.8113(6) 0.6886(5) 0.1764(11) 0.074(3) Uani 1 1 d . . . . .
H3B H 0.8378 0.6475 0.1404 0.088 Uiso 1 1 calc R U . . .
C4 C 0.8397(5) 0.7603(5) 0.1493(8) 0.057(2) Uani 1 1 d . . . . .
C5 C 0.7969(5) 0.8203(5) 0.2078(8) 0.0587(19) Uani 1 1 d . . . . .
H5A H 0.8142 0.8690 0.1918 0.070 Uiso 1 1 calc R U . . .
C6 C 0.9383(5) 0.8349(5) 0.0184(8) 0.0567(19) Uani 1 1 d . . . . .
C7 C 1.0200(5) 0.8254(5) -0.0566(9) 0.066(2) Uani 1 1 d . . . . .
H7A H 1.0268 0.7732 -0.0794 0.079 Uiso 1 1 calc R U . . .
H7B H 1.0107 0.8537 -0.1429 0.079 Uiso 1 1 calc R U . . .
C8 C 1.1043(5) 0.8524(4) 0.0361(7) 0.0485(17) Uani 1 1 d . . . . .
C9 C 1.1403(6) 0.9218(5) 0.0160(8) 0.061(2) Uani 1 1 d . . . . .
H9A H 1.1149 0.9512 -0.0591 0.073 Uiso 1 1 calc R U . . .
C10 C 1.2157(6) 0.9480(5) 0.1095(10) 0.071(2) Uani 1 1 d . . . . .
H10A H 1.2405 0.9946 0.0961 0.085 Uiso 1 1 calc R U . . .
C11 C 1.2524(5) 0.9044(5) 0.2204(9) 0.062(2) Uani 1 1 d . . . . .
H11A H 1.3024 0.9217 0.2815 0.075 Uiso 1 1 calc R U . . .
C12 C 1.2162(5) 0.8352(4) 0.2429(7) 0.0465(16) Uani 1 1 d . . . . .
C13 C 1.1436(5) 0.8104(4) 0.1509(7) 0.0458(16) Uani 1 1 d . . . . .
H13A H 1.1193 0.7638 0.1654 0.055 Uiso 1 1 calc R U . . .
C14 C 1.2569(5) 0.7897(5) 0.3679(7) 0.060(2) Uani 1 1 d . . . . .
H14A H 1.2804 0.8233 0.4435 0.071 Uiso 1 1 calc R U . . .
H14B H 1.2096 0.7598 0.3985 0.071 Uiso 1 1 calc R U . . .
C15 C 1.3322(4) 0.7390(4) 0.3387(6) 0.0390(14) Uani 1 1 d . . . . .
C16 C 1.4460(4) 0.6532(4) 0.4629(6) 0.0383(14) Uani 1 1 d . . . . .
C17 C 1.4735(5) 0.6163(4) 0.3521(7) 0.0469(16) Uani 1 1 d . . . . .
H17A H 1.4421 0.6226 0.2622 0.056 Uiso 1 1 calc R U . . .
C18 C 1.5477(5) 0.5704(4) 0.3760(8) 0.0570(19) Uani 1 1 d . . . . .
H18A H 1.5674 0.5460 0.3016 0.068 Uiso 1 1 calc R U . . .
C19 C 1.5935(5) 0.5601(5) 0.5099(8) 0.0566(19) Uani 1 1 d . . . . .
H19A H 1.6437 0.5288 0.5253 0.068 Uiso 1 1 calc R U . . .
C20 C 1.4955(5) 0.6407(4) 0.5939(7) 0.0471(16) Uani 1 1 d . . . . .
H20A H 1.4784 0.6657 0.6695 0.057 Uiso 1 1 calc R U . . .
N5 N 0.9971(8) 0.8674(6) 0.4706(13) 0.116(4) Uani 1 1 d . . . . .
C21 C 1.0312(6) 0.9731(5) 0.3115(9) 0.070(2) Uani 1 1 d . . . . .
H21A H 1.0903 0.9664 0.2863 0.084 Uiso 1 1 calc R U . . .
H21B H 1.0294 1.0193 0.3609 0.084 Uiso 1 1 calc R U . . .
H21C H 0.9865 0.9740 0.2286 0.084 Uiso 1 1 calc R U . . .
C22 C 1.0126(6) 0.9138(6) 0.3971(12) 0.075(3) Uani 1 1 d . . . . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Hg N4 2.423(6) 4_475 ?
Hg N1 2.464(7) . ?
Hg I1 2.6124(7) . ?
Hg I2 2.6389(7) . ?
O1 C6 1.208(9) . ?
O2 C15 1.218(7) . ?
N1 C1 1.317(11) . ?
N1 C5 1.352(10) . ?
N2 C6 1.352(10) . ?
N2 C4 1.392(10) . ?
N2 H2A 0.8600 . ?
N3 C15 1.353(8) . ?
N3 C16 1.391(8) . ?
N3 H3A 0.8600 . ?
N4 C20 1.322(9) . ?
N4 C19 1.336(10) . ?
N4 Hg 2.423(6) 4_676 ?
C1 C2 1.373(15) . ?
C1 H1A 0.9300 . ?
C2 C3 1.375(14) . ?
C2 H2B 0.9300 . ?
C3 C4 1.391(12) . ?
C3 H3B 0.9300 . ?
C4 C5 1.415(11) . ?
C5 H5A 0.9300 . ?
C6 C7 1.525(11) . ?
C7 C8 1.507(11) . ?
C7 H7A 0.9700 . ?
C7 H7B 0.9700 . ?
C8 C9 1.381(11) . ?
C8 C13 1.396(9) . ?
C9 C10 1.411(12) . ?
C9 H9A 0.9300 . ?
C10 C11 1.372(12) . ?
C10 H10A 0.9300 . ?
C11 C12 1.384(11) . ?
C11 H11A 0.9300 . ?
C12 C13 1.365(10) . ?
C12 C14 1.508(9) . ?
C13 H13A 0.9300 . ?
C14 C15 1.507(9) . ?
C14 H14A 0.9700 . ?
C14 H14B 0.9700 . ?
C16 C17 1.379(9) . ?
C16 C20 1.385(9) . ?
C17 C18 1.369(10) . ?
C17 H17A 0.9300 . ?
C18 C19 1.383(11) . ?
C18 H18A 0.9300 . ?
C19 H19A 0.9300 . ?
C20 H20A 0.9300 . ?
N5 C22 1.143(13) . ?
C21 C22 1.404(14) . ?
C21 H21A 0.9600 . ?
C21 H21B 0.9600 . ?
C21 H21C 0.9600 . ?

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
N4 Hg N1 83.2(2) 4_475 . ?
N4 Hg I1 99.36(14) 4_475 . ?
N1 Hg I1 105.48(17) . . ?
N4 Hg I2 107.45(14) 4_475 . ?
N1 Hg I2 103.31(16) . . ?
I1 Hg I2 142.51(3) . . ?
C1 N1 C5 120.2(8) . . ?
C1 N1 Hg 122.1(7) . . ?
C5 N1 Hg 117.1(6) . . ?
C6 N2 C4 129.4(7) . . ?
C6 N2 H2A 115.3 . . ?
C4 N2 H2A 115.3 . . ?
C15 N3 C16 127.5(5) . . ?
C15 N3 H3A 116.3 . . ?
C16 N3 H3A 116.3 . . ?
C20 N4 C19 119.4(6) . . ?
C20 N4 Hg 119.5(5) . 4_676 ?
C19 N4 Hg 121.0(5) . 4_676 ?
N1 C1 C2 121.8(10) . . ?
N1 C1 H1A 119.1 . . ?
C2 C1 H1A 119.1 . . ?
C1 C2 C3 119.7(9) . . ?
C1 C2 H2B 120.1 . . ?
C3 C2 H2B 120.1 . . ?
C2 C3 C4 119.9(9) . . ?
C2 C3 H3B 120.0 . . ?
C4 C3 H3B 120.0 . . ?
C3 C4 N2 120.3(8) . . ?
C3 C4 C5 117.1(8) . . ?
N2 C4 C5 122.6(7) . . ?
N1 C5 C4 121.2(8) . . ?
N1 C5 H5A 119.4 . . ?
C4 C5 H5A 119.4 . . ?
O1 C6 N2 123.3(8) . . ?
O1 C6 C7 122.1(8) . . ?
N2 C6 C7 114.6(7) . . ?
C8 C7 C6 109.5(6) . . ?
C8 C7 H7A 109.8 . . ?
C6 C7 H7A 109.8 . . ?
C8 C7 H7B 109.8 . . ?
C6 C7 H7B 109.8 . . ?
H7A C7 H7B 108.2 . . ?
C9 C8 C13 118.3(7) . . ?
C9 C8 C7 120.9(7) . . ?
C13 C8 C7 120.6(7) . . ?
C8 C9 C10 119.9(7) . . ?
C8 C9 H9A 120.1 . . ?
C10 C9 H9A 120.1 . . ?
C11 C10 C9 119.6(8) . . ?
C11 C10 H10A 120.2 . . ?
C9 C10 H10A 120.2 . . ?
C10 C11 C12 121.2(8) . . ?
C10 C11 H11A 119.4 . . ?
C12 C11 H11A 119.4 . . ?
C13 C12 C11 118.5(6) . . ?
C13 C12 C14 121.9(7) . . ?
C11 C12 C14 119.6(7) . . ?
C12 C13 C8 122.5(7) . . ?
C12 C13 H13A 118.7 . . ?
C8 C13 H13A 118.7 . . ?
C15 C14 C12 113.1(5) . . ?
C15 C14 H14A 109.0 . . ?
C12 C14 H14A 109.0 . . ?
C15 C14 H14B 109.0 . . ?
C12 C14 H14B 109.0 . . ?
H14A C14 H14B 107.8 . . ?
O2 C15 N3 122.6(6) . . ?
O2 C15 C14 124.3(6) . . ?
N3 C15 C14 113.1(5) . . ?
C17 C16 C20 117.2(6) . . ?
C17 C16 N3 124.8(6) . . ?
C20 C16 N3 118.0(6) . . ?
C18 C17 C16 119.3(6) . . ?
C18 C17 H17A 120.4 . . ?
C16 C17 H17A 120.4 . . ?
C17 C18 C19 120.4(7) . . ?
C17 C18 H18A 119.8 . . ?
C19 C18 H18A 119.8 . . ?
N4 C19 C18 120.3(7) . . ?
N4 C19 H19A 119.9 . . ?
C18 C19 H19A 119.9 . . ?
N4 C20 C16 123.6(6) . . ?
N4 C20 H20A 118.2 . . ?
C16 C20 H20A 118.2 . . ?
C22 C21 H21A 109.5 . . ?
C22 C21 H21B 109.5 . . ?
H21A C21 H21B 109.5 . . ?
C22 C21 H21C 109.5 . . ?
H21A C21 H21C 109.5 . . ?
H21B C21 H21C 109.5 . . ?
N5 C22 C21 177.4(11) . . ?

_refine_diff_density_max         1.235
_refine_diff_density_min         -1.452
_refine_diff_density_rms         0.126

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

data_2
_database_code_depnum_ccdc_archive 'CCDC 1588626'
_audit_update_record             
;
2017-12-01 deposited with the CCDC.
2018-03-02 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C20 H18 Br2 Hg N4 O2'
_chemical_formula_weight         706.79

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'

_space_group_crystal_system      orthorhombic
_space_group_IT_number           61
_space_group_name_H-M_alt        'P b c a'
_space_group_name_Hall           '-P 2ac 2ab'

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

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

_cell_length_a                   16.5731(7)
_cell_length_b                   14.3971(5)
_cell_length_c                   18.3341(7)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     4374.6(3)
_cell_formula_units_Z            8
_cell_measurement_temperature    300(2)
_cell_measurement_reflns_used    8188
_cell_measurement_theta_min      2.46
_cell_measurement_theta_max      28.20

_exptl_crystal_description       block
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    2.146
_exptl_crystal_F_000             2656
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.400
_exptl_crystal_size_mid          0.300
_exptl_crystal_size_min          0.200
_exptl_absorpt_coefficient_mu    10.714
_shelx_estimated_absorpt_T_min   0.099
_shelx_estimated_absorpt_T_max   0.223
_exptl_absorpt_correction_type   multi_scan
_exptl_absorpt_correction_T_min  0.2399
_exptl_absorpt_correction_T_max  0.7457
_exptl_absorpt_process_details   'sadabs v2008/1(bruker axs, 2008)'
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      300(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            21195
_diffrn_reflns_av_unetI/netI     0.0795
_diffrn_reflns_av_R_equivalents  0.0735
_diffrn_reflns_limit_h_min       -21
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_k_max       19
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_limit_l_max       24
_diffrn_reflns_theta_min         2.178
_diffrn_reflns_theta_max         28.328
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.991
_diffrn_measured_fraction_theta_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.991
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.991
_diffrn_reflns_point_group_measured_fraction_full 1.000
_reflns_number_total             5405
_reflns_number_gt                3453
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

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

_computing_data_collection       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0186P)²] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     'SHELXL-2014/7 (Sheldrick 2014'
_refine_ls_extinction_coef       0.00088(5)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_number_reflns         5405
_refine_ls_number_parameters     263
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0789
_refine_ls_R_factor_gt           0.0403
_refine_ls_wR_factor_ref         0.0852
_refine_ls_wR_factor_gt          0.0746
_refine_ls_goodness_of_fit_ref   0.966
_refine_ls_restrained_S_all      0.966
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Hg Hg 0.62117(2) 0.51566(2) 0.44882(2) 0.04356(10) Uani 1 1 d . . . . .
Br1 Br 0.58509(5) 0.35100(4) 0.46717(3) 0.0656(2) Uani 1 1 d . . . . .
Br2 Br 0.59931(4) 0.66037(5) 0.37895(4) 0.0664(2) Uani 1 1 d . . . . .
O1 O 0.8205(2) 0.7053(3) 0.2863(2) 0.0599(12) Uani 1 1 d . . . . .
O2 O 0.9044(2) 1.1526(2) 0.1272(2) 0.0458(10) Uani 1 1 d . . . . .
N1 N 0.7665(3) 0.4982(3) 0.4248(2) 0.0388(11) Uani 1 1 d . . . . .
N2 N 0.9260(2) 0.6458(3) 0.3488(2) 0.0341(10) Uani 1 1 d . . . . .
H2A H 0.9762 0.6538 0.3592 0.041 Uiso 1 1 calc R U . . .
N3 N 0.8090(3) 1.2355(3) 0.1852(2) 0.0431(11) Uani 1 1 d . . . . .
H3A H 0.7647 1.2328 0.2096 0.052 Uiso 1 1 calc R U . . .
N4 N 0.8750(3) 1.4331(3) 0.0743(2) 0.0378(11) Uani 1 1 d . . . . .
C1 C 0.8102(4) 0.4230(4) 0.4420(3) 0.0482(15) Uani 1 1 d . . . . .
H1A H 0.7839 0.3713 0.4608 0.058 Uiso 1 1 calc R U . . .
C2 C 0.8917(4) 0.4195(4) 0.4329(3) 0.0490(15) Uani 1 1 d . . . . .
H2B H 0.9205 0.3673 0.4474 0.059 Uiso 1 1 calc R U . . .
C3 C 0.9306(4) 0.4930(3) 0.4024(3) 0.0429(14) Uani 1 1 d . . . . .
H3B H 0.9861 0.4914 0.3950 0.051 Uiso 1 1 calc R U . . .
C4 C 0.8861(3) 0.5702(3) 0.3824(2) 0.0330(12) Uani 1 1 d . . . . .
C5 C 0.8045(3) 0.5715(3) 0.3960(3) 0.0364(12) Uani 1 1 d . . . . .
H5A H 0.7751 0.6246 0.3849 0.044 Uiso 1 1 calc R U . . .
C6 C 0.8918(3) 0.7070(3) 0.3013(3) 0.0335(12) Uani 1 1 d . . . . .
C7 C 0.9501(3) 0.7778(3) 0.2710(3) 0.0401(13) Uani 1 1 d . . . . .
H7A H 0.9693 0.8168 0.3105 0.048 Uiso 1 1 calc R U . . .
H7B H 0.9964 0.7458 0.2506 0.048 Uiso 1 1 calc R U . . .
C8 C 0.9129(3) 0.8383(3) 0.2132(3) 0.0341(12) Uani 1 1 d . . . . .
C9 C 0.9077(3) 0.8069(3) 0.1421(3) 0.0409(13) Uani 1 1 d . . . . .
H9A H 0.9285 0.7491 0.1296 0.049 Uiso 1 1 calc R U . . .
C10 C 0.8712(4) 0.8622(4) 0.0891(3) 0.0488(15) Uani 1 1 d . . . . .
H10A H 0.8683 0.8415 0.0412 0.059 Uiso 1 1 calc R U . . .
C11 C 0.8396(3) 0.9467(4) 0.1073(3) 0.0474(14) Uani 1 1 d . . . . .
H11A H 0.8152 0.9830 0.0715 0.057 Uiso 1 1 calc R U . . .
C12 C 0.8435(3) 0.9786(3) 0.1778(3) 0.0367(12) Uani 1 1 d . . . . .
C13 C 0.8799(3) 0.9239(4) 0.2295(3) 0.0384(13) Uani 1 1 d . . . . .
H13A H 0.8824 0.9453 0.2773 0.046 Uiso 1 1 calc R U . . .
C14 C 0.8055(3) 1.0706(3) 0.1984(3) 0.0506(15) Uani 1 1 d . . . . .
H14A H 0.7494 1.0698 0.1833 0.061 Uiso 1 1 calc R U . . .
H14B H 0.8064 1.0764 0.2511 0.061 Uiso 1 1 calc R U . . .
C15 C 0.8453(3) 1.1549(3) 0.1661(3) 0.0332(12) Uani 1 1 d . . . . .
C16 C 0.8404(3) 1.3239(3) 0.1669(3) 0.0349(12) Uani 1 1 d . . . . .
C17 C 0.8618(3) 1.3860(4) 0.2189(3) 0.0475(15) Uani 1 1 d . . . . .
H17A H 0.8558 1.3715 0.2681 0.057 Uiso 1 1 calc R U . . .
C18 C 0.8927(4) 1.4709(4) 0.1984(3) 0.0518(17) Uani 1 1 d . . . . .
H18A H 0.9101 1.5131 0.2334 0.062 Uiso 1 1 calc R U . . .
C19 C 0.8975(3) 1.4921(3) 0.1265(3) 0.0397(13) Uani 1 1 d . . . . .
H19A H 0.9173 1.5501 0.1131 0.048 Uiso 1 1 calc R U . . .
C20 C 0.8483(3) 1.3494(3) 0.0937(3) 0.0382(13) Uani 1 1 d . . . . .
H20A H 0.8346 1.3069 0.0576 0.046 Uiso 1 1 calc R U . . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Hg N4 2.417(4) 2_675 ?
Hg N1 2.461(5) . ?
Hg Br1 2.4679(6) . ?
Hg Br2 2.4725(6) . ?
O1 C6 1.213(5) . ?
O2 C15 1.212(6) . ?
N1 C5 1.338(6) . ?
N1 C1 1.341(6) . ?
N2 C6 1.362(6) . ?
N2 C4 1.416(6) . ?
N2 H2A 0.8600 . ?
N3 C15 1.352(6) . ?
N3 C16 1.416(6) . ?
N3 H3A 0.8600 . ?
N4 C20 1.332(6) . ?
N4 C19 1.333(6) . ?
N4 Hg 2.417(4) 2_674 ?
C1 C2 1.360(8) . ?
C1 H1A 0.9300 . ?
C2 C3 1.359(7) . ?
C2 H2B 0.9300 . ?
C3 C4 1.383(6) . ?
C3 H3B 0.9300 . ?
C4 C5 1.374(7) . ?
C5 H5A 0.9300 . ?
C6 C7 1.511(7) . ?
C7 C8 1.504(6) . ?
C7 H7A 0.9700 . ?
C7 H7B 0.9700 . ?
C8 C13 1.382(6) . ?
C8 C9 1.382(6) . ?
C9 C10 1.393(7) . ?
C9 H9A 0.9300 . ?
C10 C11 1.365(7) . ?
C10 H10A 0.9300 . ?
C11 C12 1.374(7) . ?
C11 H11A 0.9300 . ?
C12 C13 1.372(7) . ?
C12 C14 1.515(7) . ?
C13 H13A 0.9300 . ?
C14 C15 1.503(6) . ?
C14 H14A 0.9700 . ?
C14 H14B 0.9700 . ?
C16 C17 1.356(7) . ?
C16 C20 1.398(6) . ?
C17 C18 1.377(8) . ?
C17 H17A 0.9300 . ?
C18 C19 1.355(8) . ?
C18 H18A 0.9300 . ?
C19 H19A 0.9300 . ?
C20 H20A 0.9300 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
N4 Hg N1 100.14(14) 2_675 . ?
N4 Hg Br1 99.77(10) 2_675 . ?
N1 Hg Br1 99.42(10) . . ?
N4 Hg Br2 103.88(10) 2_675 . ?
N1 Hg Br2 97.84(10) . . ?
Br1 Hg Br2 147.62(3) . . ?
C5 N1 C1 118.3(5) . . ?
C5 N1 Hg 116.9(3) . . ?
C1 N1 Hg 124.7(4) . . ?
C6 N2 C4 125.5(4) . . ?
C6 N2 H2A 117.3 . . ?
C4 N2 H2A 117.3 . . ?
C15 N3 C16 123.1(4) . . ?
C15 N3 H3A 118.5 . . ?
C16 N3 H3A 118.5 . . ?
C20 N4 C19 118.6(5) . . ?
C20 N4 Hg 122.6(3) . 2_674 ?
C19 N4 Hg 118.8(3) . 2_674 ?
N1 C1 C2 122.6(5) . . ?
N1 C1 H1A 118.7 . . ?
C2 C1 H1A 118.7 . . ?
C3 C2 C1 119.5(5) . . ?
C3 C2 H2B 120.3 . . ?
C1 C2 H2B 120.3 . . ?
C2 C3 C4 118.8(5) . . ?
C2 C3 H3B 120.6 . . ?
C4 C3 H3B 120.6 . . ?
C5 C4 C3 119.1(5) . . ?
C5 C4 N2 121.9(4) . . ?
C3 C4 N2 118.9(5) . . ?
N1 C5 C4 121.7(5) . . ?
N1 C5 H5A 119.2 . . ?
C4 C5 H5A 119.2 . . ?
O1 C6 N2 122.6(5) . . ?
O1 C6 C7 123.5(4) . . ?
N2 C6 C7 113.9(4) . . ?
C8 C7 C6 112.8(4) . . ?
C8 C7 H7A 109.0 . . ?
C6 C7 H7A 109.0 . . ?
C8 C7 H7B 109.0 . . ?
C6 C7 H7B 109.0 . . ?
H7A C7 H7B 107.8 . . ?
C13 C8 C9 118.0(5) . . ?
C13 C8 C7 121.7(4) . . ?
C9 C8 C7 120.2(5) . . ?
C8 C9 C10 119.9(5) . . ?
C8 C9 H9A 120.1 . . ?
C10 C9 H9A 120.1 . . ?
C11 C10 C9 120.4(5) . . ?
C11 C10 H10A 119.8 . . ?
C9 C10 H10A 119.8 . . ?
C10 C11 C12 120.6(5) . . ?
C10 C11 H11A 119.7 . . ?
C12 C11 H11A 119.7 . . ?
C13 C12 C11 118.6(5) . . ?
C13 C12 C14 120.8(5) . . ?
C11 C12 C14 120.5(5) . . ?
C12 C13 C8 122.5(5) . . ?
C12 C13 H13A 118.8 . . ?
C8 C13 H13A 118.8 . . ?
C15 C14 C12 115.1(4) . . ?
C15 C14 H14A 108.5 . . ?
C12 C14 H14A 108.5 . . ?
C15 C14 H14B 108.5 . . ?
C12 C14 H14B 108.5 . . ?
H14A C14 H14B 107.5 . . ?
O2 C15 N3 122.4(4) . . ?
O2 C15 C14 124.4(5) . . ?
N3 C15 C14 113.2(4) . . ?
C17 C16 C20 118.6(5) . . ?
C17 C16 N3 121.5(4) . . ?
C20 C16 N3 119.9(4) . . ?
C16 C17 C18 119.3(5) . . ?
C16 C17 H17A 120.3 . . ?
C18 C17 H17A 120.3 . . ?
C19 C18 C17 119.2(5) . . ?
C19 C18 H18A 120.4 . . ?
C17 C18 H18A 120.4 . . ?
N4 C19 C18 122.6(5) . . ?
N4 C19 H19A 118.7 . . ?
C18 C19 H19A 118.7 . . ?
N4 C20 C16 121.6(5) . . ?
N4 C20 H20A 119.2 . . ?
C16 C20 H20A 119.2 . . ?

_refine_diff_density_max         1.274
_refine_diff_density_min         -1.243
_refine_diff_density_rms         0.163

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

data_3
_database_code_depnum_ccdc_archive 'CCDC 1588627'
_audit_update_record             
;
2017-12-01 deposited with the CCDC.
2018-03-02 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C20 H18 Hg I2 N4 O2'
_chemical_formula_weight         800.77

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'

_space_group_crystal_system      orthorhombic
_space_group_IT_number           61
_space_group_name_H-M_alt        'P b c a'
_space_group_name_Hall           '-P 2ac 2ab'

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

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

_cell_length_a                   16.9633(5)
_cell_length_b                   9.3636(2)
_cell_length_c                   29.0993(7)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     4622.1(2)
_cell_formula_units_Z            8
_cell_measurement_temperature    299(2)
_cell_measurement_reflns_used    5005
_cell_measurement_theta_min      2.40
_cell_measurement_theta_max      27.00

_exptl_crystal_description       column
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    2.302
_exptl_crystal_F_000             2944
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.500
_exptl_crystal_size_mid          0.300
_exptl_crystal_size_min          0.050
_exptl_absorpt_coefficient_mu    9.354
_shelx_estimated_absorpt_T_min   0.089
_shelx_estimated_absorpt_T_max   0.652
_exptl_absorpt_correction_type   multi_scan
_exptl_absorpt_correction_T_min  0.5060
_exptl_absorpt_correction_T_max  0.7457
_exptl_absorpt_process_details   'sadabs v2008/1(bruker axs, 2008)'
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      299(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            20835
_diffrn_reflns_av_unetI/netI     0.0556
_diffrn_reflns_av_R_equivalents  0.0695
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_h_max       20
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_l_min       -34
_diffrn_reflns_limit_l_max       35
_diffrn_reflns_theta_min         2.401
_diffrn_reflns_theta_max         25.996
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measured_fraction_theta_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_point_group_measured_fraction_full 0.999
_reflns_number_total             4533
_reflns_number_gt                2832
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

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

_computing_data_collection       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0148P)²] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         4533
_refine_ls_number_parameters     282
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0771
_refine_ls_R_factor_gt           0.0334
_refine_ls_wR_factor_ref         0.0577
_refine_ls_wR_factor_gt          0.0487
_refine_ls_goodness_of_fit_ref   0.975
_refine_ls_restrained_S_all      0.975
_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_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Hg Hg 0.50202(2) 0.46094(3) 0.65127(2) 0.04237(8) Uani 1 1 d . . . . .
I1 I 0.5225(7) 0.5948(7) 0.5706(3) 0.0541(9) Uani 0.67(6) 1 d . . P . .
I1' I 0.5114(16) 0.5960(14) 0.5735(5) 0.061(3) Uani 0.33(6) 1 d . . P . .
I2 I 0.5675(10) 0.388(3) 0.7298(4) 0.061(2) Uani 0.36(5) 1 d . . P . .
I2' I 0.5744(5) 0.4143(14) 0.7303(2) 0.0544(12) Uani 0.64(5) 1 d . . P . .
O1 O 0.3093(2) 0.3820(5) 0.80558(13) 0.0459(11) Uani 1 1 d . . . . .
O2 O 0.2329(3) 0.6756(4) 1.04130(15) 0.0562(13) Uani 1 1 d . . . . .
N1 N 0.3738(3) 0.5480(5) 0.67929(16) 0.0382(13) Uani 1 1 d . . . . .
N2 N 0.2673(3) 0.6045(5) 0.78758(15) 0.0356(12) Uani 1 1 d . . . . .
H2A H 0.2475 0.6810 0.7991 0.043 Uiso 1 1 calc R U . . .
N3 N 0.1931(3) 0.9052(5) 1.04323(16) 0.0401(13) Uani 1 1 d . . . . .
H3A H 0.1977 0.9864 1.0297 0.048 Uiso 1 1 calc R U . . .
N4 N 0.0511(3) 0.7653(5) 1.12730(17) 0.0422(13) Uani 1 1 d . . . . .
C1 C 0.3294(4) 0.6293(7) 0.6514(2) 0.0417(16) Uani 1 1 d . . . . .
H1A H 0.3438 0.6364 0.6206 0.050 Uiso 1 1 calc R U . . .
C2 C 0.2640(4) 0.7020(7) 0.6660(2) 0.0464(18) Uani 1 1 d . . . . .
H2B H 0.2344 0.7563 0.6456 0.056 Uiso 1 1 calc R U . . .
C3 C 0.2432(4) 0.6930(6) 0.7115(2) 0.0408(16) Uani 1 1 d . . . . .
H3B H 0.1994 0.7422 0.7224 0.049 Uiso 1 1 calc R U . . .
C4 C 0.2879(3) 0.6104(6) 0.74088(18) 0.0304(14) Uani 1 1 d . . . . .
C5 C 0.3536(3) 0.5406(6) 0.72379(18) 0.0326(14) Uani 1 1 d . . . . .
H5A H 0.3846 0.4870 0.7437 0.039 Uiso 1 1 calc R U . . .
C6 C 0.2750(3) 0.4918(7) 0.8166(2) 0.0348(15) Uani 1 1 d . . . . .
C7 C 0.2372(3) 0.5130(7) 0.86326(18) 0.0395(16) Uani 1 1 d . . . . .
H7A H 0.2132 0.4239 0.8729 0.047 Uiso 1 1 calc R U . . .
H7B H 0.1956 0.5837 0.8606 0.047 Uiso 1 1 calc R U . . .
C8 C 0.2956(3) 0.5613(6) 0.89991(19) 0.0307(14) Uani 1 1 d . . . . .
C9 C 0.2767(3) 0.6754(6) 0.9283(2) 0.0349(15) Uani 1 1 d . . . . .
H9A H 0.2289 0.7223 0.9240 0.042 Uiso 1 1 calc R U . . .
C10 C 0.3267(3) 0.7216(6) 0.9628(2) 0.0353(15) Uani 1 1 d . . . . .
C11 C 0.3965(3) 0.6506(7) 0.9695(2) 0.0419(17) Uani 1 1 d . . . . .
H11A H 0.4310 0.6802 0.9925 0.050 Uiso 1 1 calc R U . . .
C12 C 0.4157(4) 0.5347(7) 0.9421(2) 0.0514(18) Uani 1 1 d . . . . .
H12A H 0.4628 0.4863 0.9471 0.062 Uiso 1 1 calc R U . . .
C13 C 0.3663(4) 0.4904(7) 0.9077(2) 0.0419(17) Uani 1 1 d . . . . .
H13A H 0.3801 0.4126 0.8895 0.050 Uiso 1 1 calc R U . . .
C14 C 0.3016(3) 0.8428(6) 0.99344(19) 0.0379(16) Uani 1 1 d . . . . .
H14A H 0.3473 0.8787 1.0098 0.045 Uiso 1 1 calc R U . . .
H14B H 0.2811 0.9198 0.9746 0.045 Uiso 1 1 calc R U . . .
C15 C 0.2397(3) 0.7989(7) 1.02764(19) 0.0320(14) Uani 1 1 d . . . . .
C16 C 0.1384(3) 0.8983(7) 1.07867(19) 0.0336(14) Uani 1 1 d . . . . .
C17 C 0.1193(4) 1.0200(7) 1.1027(2) 0.0456(17) Uani 1 1 d . . . . .
H17A H 0.1408 1.1073 1.0941 0.055 Uiso 1 1 calc R U . . .
C18 C 0.0687(4) 1.0128(7) 1.1391(2) 0.054(2) Uani 1 1 d . . . . .
H18A H 0.0559 1.0949 1.1555 0.064 Uiso 1 1 calc R U . . .
C19 C 0.0369(4) 0.8835(7) 1.1514(2) 0.0493(17) Uani 1 1 d . . . . .
H19A H 0.0046 0.8783 1.1771 0.059 Uiso 1 1 calc R U . . .
C20 C 0.1000(3) 0.7722(7) 1.0915(2) 0.0396(16) Uani 1 1 d . . . . .
H20A H 0.1089 0.6899 1.0744 0.048 Uiso 1 1 calc R U . . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Hg N4 2.405(5) 2_564 ?
Hg N1 2.462(5) . ?
Hg I1' 2.598(16) . ?
Hg I2 2.630(13) . ?
Hg I2' 2.644(7) . ?
Hg I1 2.683(8) . ?
O1 C6 1.224(7) . ?
O2 C15 1.226(6) . ?
N1 C5 1.341(6) . ?
N1 C1 1.343(7) . ?
N2 C6 1.358(7) . ?
N2 C4 1.404(6) . ?
N2 H2A 0.8600 . ?
N3 C15 1.351(7) . ?
N3 C16 1.388(7) . ?
N3 H3A 0.8600 . ?
N4 C19 1.332(7) . ?
N4 C20 1.333(7) . ?
N4 Hg 2.405(5) 2_565 ?
C1 C2 1.370(8) . ?
C1 H1A 0.9300 . ?
C2 C3 1.371(8) . ?
C2 H2B 0.9300 . ?
C3 C4 1.380(7) . ?
C3 H3B 0.9300 . ?
C4 C5 1.385(7) . ?
C5 H5A 0.9300 . ?
C6 C7 1.514(8) . ?
C7 C8 1.525(8) . ?
C7 H7A 0.9700 . ?
C7 H7B 0.9700 . ?
C8 C9 1.388(8) . ?
C8 C13 1.390(8) . ?
C9 C10 1.383(7) . ?
C9 H9A 0.9300 . ?
C10 C11 1.373(8) . ?
C10 C14 1.505(8) . ?
C11 C12 1.387(8) . ?
C11 H11A 0.9300 . ?
C12 C13 1.369(8) . ?
C12 H12A 0.9300 . ?
C13 H13A 0.9300 . ?
C14 C15 1.504(7) . ?
C14 H14A 0.9700 . ?
C14 H14B 0.9700 . ?
C16 C17 1.375(8) . ?
C16 C20 1.400(8) . ?
C17 C18 1.366(8) . ?
C17 H17A 0.9300 . ?
C18 C19 1.373(9) . ?
C18 H18A 0.9300 . ?
C19 H19A 0.9300 . ?
C20 H20A 0.9300 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
N4 Hg N1 93.25(16) 2_564 . ?
N4 Hg I1' 101.5(3) 2_564 . ?
N1 Hg I1' 100.5(6) . . ?
N4 Hg I2 100.5(6) 2_564 . ?
N1 Hg I2 99.9(3) . . ?
I1' Hg I2 149.0(7) . . ?
N4 Hg I2' 106.3(3) 2_564 . ?
N1 Hg I2' 100.18(17) . . ?
I1' Hg I2' 144.1(5) . . ?
I2 Hg I2' 5.9(6) . . ?
N4 Hg I1 101.91(17) 2_564 . ?
N1 Hg I1 104.4(3) . . ?
I1' Hg I1 4.1(7) . . ?
I2 Hg I1 145.7(5) . . ?
I2' Hg I1 141.1(3) . . ?
C5 N1 C1 118.1(5) . . ?
C5 N1 Hg 121.8(4) . . ?
C1 N1 Hg 118.8(4) . . ?
C6 N2 C4 127.5(5) . . ?
C6 N2 H2A 116.3 . . ?
C4 N2 H2A 116.3 . . ?
C15 N3 C16 127.3(5) . . ?
C15 N3 H3A 116.3 . . ?
C16 N3 H3A 116.3 . . ?
C19 N4 C20 118.9(6) . . ?
C19 N4 Hg 120.8(4) . 2_565 ?
C20 N4 Hg 120.2(4) . 2_565 ?
N1 C1 C2 123.1(6) . . ?
N1 C1 H1A 118.4 . . ?
C2 C1 H1A 118.4 . . ?
C1 C2 C3 118.6(6) . . ?
C1 C2 H2B 120.7 . . ?
C3 C2 H2B 120.7 . . ?
C2 C3 C4 119.4(6) . . ?
C2 C3 H3B 120.3 . . ?
C4 C3 H3B 120.3 . . ?
C3 C4 C5 118.9(5) . . ?
C3 C4 N2 119.1(5) . . ?
C5 C4 N2 122.0(5) . . ?
N1 C5 C4 121.8(5) . . ?
N1 C5 H5A 119.1 . . ?
C4 C5 H5A 119.1 . . ?
O1 C6 N2 122.4(6) . . ?
O1 C6 C7 123.1(6) . . ?
N2 C6 C7 114.5(5) . . ?
C6 C7 C8 113.0(5) . . ?
C6 C7 H7A 109.0 . . ?
C8 C7 H7A 109.0 . . ?
C6 C7 H7B 109.0 . . ?
C8 C7 H7B 109.0 . . ?
H7A C7 H7B 107.8 . . ?
C9 C8 C13 118.1(5) . . ?
C9 C8 C7 119.7(5) . . ?
C13 C8 C7 122.2(6) . . ?
C10 C9 C8 122.1(6) . . ?
C10 C9 H9A 119.0 . . ?
C8 C9 H9A 119.0 . . ?
C11 C10 C9 118.7(6) . . ?
C11 C10 C14 121.7(6) . . ?
C9 C10 C14 119.5(5) . . ?
C10 C11 C12 120.0(6) . . ?
C10 C11 H11A 120.0 . . ?
C12 C11 H11A 120.0 . . ?
C13 C12 C11 121.0(6) . . ?
C13 C12 H12A 119.5 . . ?
C11 C12 H12A 119.5 . . ?
C12 C13 C8 120.2(6) . . ?
C12 C13 H13A 119.9 . . ?
C8 C13 H13A 119.9 . . ?
C15 C14 C10 112.5(5) . . ?
C15 C14 H14A 109.1 . . ?
C10 C14 H14A 109.1 . . ?
C15 C14 H14B 109.1 . . ?
C10 C14 H14B 109.1 . . ?
H14A C14 H14B 107.8 . . ?
O2 C15 N3 122.0(6) . . ?
O2 C15 C14 122.5(5) . . ?
N3 C15 C14 115.4(5) . . ?
C17 C16 N3 119.7(6) . . ?
C17 C16 C20 117.0(5) . . ?
N3 C16 C20 123.3(6) . . ?
C18 C17 C16 120.1(6) . . ?
C18 C17 H17A 119.9 . . ?
C16 C17 H17A 119.9 . . ?
C17 C18 C19 119.5(6) . . ?
C17 C18 H18A 120.3 . . ?
C19 C18 H18A 120.3 . . ?
N4 C19 C18 121.7(6) . . ?
N4 C19 H19A 119.1 . . ?
C18 C19 H19A 119.1 . . ?
N4 C20 C16 122.6(6) . . ?
N4 C20 H20A 118.7 . . ?
C16 C20 H20A 118.7 . . ?

_refine_diff_density_max         0.697
_refine_diff_density_min         -0.627
_refine_diff_density_rms         0.130

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

data_4
_database_code_depnum_ccdc_archive 'CCDC 1588628'
_audit_update_record             
;
2017-12-01 deposited with the CCDC.
2018-03-02 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C22 H21 Br2 Hg N5 O2'
_chemical_formula_weight         747.85

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'

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

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

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

_cell_length_a                   14.4848(6)
_cell_length_b                   18.1541(7)
_cell_length_c                   9.5331(3)
_cell_angle_alpha                90
_cell_angle_beta                 98.561(3)
_cell_angle_gamma                90
_cell_volume                     2478.88(16)
_cell_formula_units_Z            4
_cell_measurement_temperature    299(2)
_cell_measurement_reflns_used    4944
_cell_measurement_theta_min      2.24
_cell_measurement_theta_max      24.95

_exptl_crystal_description       Column
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    2.004
_exptl_crystal_F_000             1416
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.400
_exptl_crystal_size_mid          0.200
_exptl_crystal_size_min          0.050
_exptl_absorpt_coefficient_mu    9.461
_shelx_estimated_absorpt_T_min   0.116
_shelx_estimated_absorpt_T_max   0.649
_exptl_absorpt_correction_type   multi_scan
_exptl_absorpt_correction_T_min  0.4659
_exptl_absorpt_correction_T_max  0.7457
_exptl_absorpt_process_details   'SADABS V2008/1 (Bruker AXS, 2008)'
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      299(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            20681
_diffrn_reflns_av_unetI/netI     0.0912
_diffrn_reflns_av_R_equivalents  0.0931
_diffrn_reflns_limit_h_min       -17
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_k_min       -21
_diffrn_reflns_limit_k_max       22
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_theta_min         1.811
_diffrn_reflns_theta_max         25.998
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measured_fraction_theta_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 1.000
_diffrn_reflns_point_group_measured_fraction_full 1.000
_reflns_number_total             4870
_reflns_number_gt                2969
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

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

_computing_data_collection       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0286P)²] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         4870
_refine_ls_number_parameters     289
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1003
_refine_ls_R_factor_gt           0.0471
_refine_ls_wR_factor_ref         0.1071
_refine_ls_wR_factor_gt          0.0899
_refine_ls_goodness_of_fit_ref   1.002
_refine_ls_restrained_S_all      1.002
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Hg Hg 0.64454(2) 0.42004(2) 0.86611(3) 0.06407(16) Uani 1 1 d . . . . .
Br1 Br 0.76231(7) 0.51772(6) 0.85874(11) 0.0892(4) Uani 1 1 d . . . . .
Br2 Br 0.52511(7) 0.36707(8) 0.99575(10) 0.1051(4) Uani 1 1 d . . . . .
O1 O 0.9015(4) 0.3968(3) 0.5278(6) 0.0612(15) Uani 1 1 d . . . . .
O2 O 1.3524(4) 0.2318(3) 0.7292(5) 0.0504(13) Uani 1 1 d . . . . .
N1 N 0.7287(4) 0.3118(4) 0.7959(7) 0.0538(17) Uani 1 1 d . . . . .
N2 N 0.9084(4) 0.2733(3) 0.5699(6) 0.0489(16) Uani 1 1 d . . . . .
H2A H 0.9375 0.2339 0.5521 0.059 Uiso 1 1 calc R U . . .
N3 N 1.3699(4) 0.2025(3) 0.9621(5) 0.0393(14) Uani 1 1 d . . . . .
H3A H 1.3464 0.2095 1.0387 0.047 Uiso 1 1 calc R U . . .
N4 N 1.5624(4) 0.0918(3) 1.1284(6) 0.0424(15) Uani 1 1 d . . . . .
C1 C 0.7014(6) 0.2430(6) 0.8153(9) 0.069(3) Uani 1 1 d . . . . .
H1A H 0.6544 0.2351 0.8702 0.083 Uiso 1 1 calc R U . . .
C2 C 0.7400(7) 0.1830(6) 0.7573(9) 0.071(3) Uani 1 1 d . . . . .
H2B H 0.7203 0.1355 0.7747 0.085 Uiso 1 1 calc R U . . .
C3 C 0.8066(6) 0.1938(5) 0.6755(9) 0.056(2) Uani 1 1 d . . . . .
H3B H 0.8324 0.1539 0.6343 0.067 Uiso 1 1 calc R U . . .
C4 C 0.8364(5) 0.2641(4) 0.6527(7) 0.0434(19) Uani 1 1 d . . . . .
C5 C 0.7954(5) 0.3217(5) 0.7143(8) 0.053(2) Uani 1 1 d . . . . .
H5A H 0.8148 0.3695 0.6987 0.064 Uiso 1 1 calc R U . . .
C6 C 0.9376(5) 0.3368(5) 0.5144(7) 0.0461(19) Uani 1 1 d . . . . .
C7 C 1.0227(5) 0.3287(4) 0.4391(7) 0.051(2) Uani 1 1 d . . . . .
H7A H 1.0312 0.2775 0.4154 0.061 Uiso 1 1 calc R U . . .
H7B H 1.0141 0.3571 0.3520 0.061 Uiso 1 1 calc R U . . .
C8 C 1.1072(5) 0.3562(4) 0.5368(6) 0.0342(16) Uani 1 1 d . . . . .
C9 C 1.1444(5) 0.4244(4) 0.5171(8) 0.051(2) Uani 1 1 d . . . . .
H9A H 1.1204 0.4525 0.4385 0.062 Uiso 1 1 calc R U . . .
C10 C 1.2169(6) 0.4511(5) 0.6130(8) 0.056(2) Uani 1 1 d . . . . .
H10A H 1.2404 0.4979 0.5994 0.067 Uiso 1 1 calc R U . . .
C11 C 1.2555(5) 0.4105(4) 0.7281(8) 0.053(2) Uani 1 1 d . . . . .
H11A H 1.3060 0.4286 0.7901 0.063 Uiso 1 1 calc R U . . .
C12 C 1.2185(5) 0.3422(4) 0.7509(7) 0.0397(18) Uani 1 1 d . . . . .
C13 C 1.1452(5) 0.3149(4) 0.6541(6) 0.0389(17) Uani 1 1 d . . . . .
H13A H 1.1212 0.2684 0.6679 0.047 Uiso 1 1 calc R U . . .
C14 C 1.2586(5) 0.2962(4) 0.8779(7) 0.050(2) Uani 1 1 d . . . . .
H14A H 1.2871 0.3287 0.9528 0.060 Uiso 1 1 calc R U . . .
H14B H 1.2081 0.2702 0.9127 0.060 Uiso 1 1 calc R U . . .
C15 C 1.3305(5) 0.2408(4) 0.8464(7) 0.0370(17) Uani 1 1 d . . . . .
C16 C 1.4436(5) 0.1533(4) 0.9711(6) 0.0349(16) Uani 1 1 d . . . . .
C17 C 1.4743(5) 0.1185(4) 0.8564(7) 0.0401(17) Uani 1 1 d . . . . .
H17A H 1.4454 0.1273 0.7642 0.048 Uiso 1 1 calc R U . . .
C18 C 1.5478(6) 0.0710(4) 0.8825(8) 0.051(2) Uani 1 1 d . . . . .
H18A H 1.5687 0.0466 0.8074 0.061 Uiso 1 1 calc R U . . .
C19 C 1.5908(6) 0.0590(4) 1.0168(8) 0.053(2) Uani 1 1 d . . . . .
H19A H 1.6414 0.0271 1.0317 0.063 Uiso 1 1 calc R U . . .
C20 C 1.4916(5) 0.1378(4) 1.1041(7) 0.0433(19) Uani 1 1 d . . . . .
H20A H 1.4726 0.1613 1.1816 0.052 Uiso 1 1 calc R U . . .
C21 C 1.0297(6) 0.4724(5) 0.8188(8) 0.065(2) Uani 1 1 d . . . . .
H21A H 1.0865 0.4656 0.7797 0.097 Uiso 1 1 calc R U . . .
H21B H 1.0343 0.5163 0.8754 0.097 Uiso 1 1 calc R U . . .
H21C H 0.9782 0.4769 0.7432 0.097 Uiso 1 1 calc R U . . .
C22 C 1.0145(6) 0.4089(6) 0.9074(11) 0.063(3) Uani 1 1 d . . . . .
N5 N 1.0017(7) 0.3612(5) 0.9772(11) 0.097(3) Uani 1 1 d . . . . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Hg N4 2.407(5) 4_465 ?
Hg N1 2.457(7) . ?
Hg Br2 2.4659(11) . ?
Hg Br1 2.4688(10) . ?
O1 C6 1.223(8) . ?
O2 C15 1.217(7) . ?
N1 C1 1.332(10) . ?
N1 C5 1.340(9) . ?
N2 C6 1.362(9) . ?
N2 C4 1.408(9) . ?
N2 H2A 0.8600 . ?
N3 C15 1.356(7) . ?
N3 C16 1.383(8) . ?
N3 H3A 0.8600 . ?
N4 C20 1.316(8) . ?
N4 C19 1.336(9) . ?
N4 Hg 2.407(5) 4_666 ?
C1 C2 1.377(12) . ?
C1 H1A 0.9300 . ?
C2 C3 1.341(11) . ?
C2 H2B 0.9300 . ?
C3 C4 1.375(10) . ?
C3 H3B 0.9300 . ?
C4 C5 1.376(10) . ?
C5 H5A 0.9300 . ?
C6 C7 1.524(10) . ?
C7 C8 1.508(9) . ?
C7 H7A 0.9700 . ?
C7 H7B 0.9700 . ?
C8 C9 1.374(9) . ?
C8 C13 1.390(8) . ?
C9 C10 1.375(10) . ?
C9 H9A 0.9300 . ?
C10 C11 1.371(10) . ?
C10 H10A 0.9300 . ?
C11 C12 1.380(10) . ?
C11 H11A 0.9300 . ?
C12 C13 1.391(9) . ?
C12 C14 1.514(9) . ?
C13 H13A 0.9300 . ?
C14 C15 1.509(9) . ?
C14 H14A 0.9700 . ?
C14 H14B 0.9700 . ?
C16 C20 1.381(8) . ?
C16 C17 1.393(9) . ?
C17 C18 1.363(10) . ?
C17 H17A 0.9300 . ?
C18 C19 1.355(10) . ?
C18 H18A 0.9300 . ?
C19 H19A 0.9300 . ?
C20 H20A 0.9300 . ?
C21 C22 1.465(13) . ?
C21 H21A 0.9600 . ?
C21 H21B 0.9600 . ?
C21 H21C 0.9600 . ?
C22 N5 1.123(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
N4 Hg N1 82.40(19) 4_465 . ?
N4 Hg Br2 98.73(14) 4_465 . ?
N1 Hg Br2 103.79(17) . . ?
N4 Hg Br1 106.51(14) 4_465 . ?
N1 Hg Br1 101.15(16) . . ?
Br2 Hg Br1 146.47(4) . . ?
C1 N1 C5 117.5(8) . . ?
C1 N1 Hg 122.9(6) . . ?
C5 N1 Hg 118.7(6) . . ?
C6 N2 C4 128.0(7) . . ?
C6 N2 H2A 116.0 . . ?
C4 N2 H2A 116.0 . . ?
C15 N3 C16 127.5(6) . . ?
C15 N3 H3A 116.2 . . ?
C16 N3 H3A 116.2 . . ?
C20 N4 C19 117.8(6) . . ?
C20 N4 Hg 119.0(5) . 4_666 ?
C19 N4 Hg 122.9(5) . 4_666 ?
N1 C1 C2 122.7(9) . . ?
N1 C1 H1A 118.7 . . ?
C2 C1 H1A 118.7 . . ?
C3 C2 C1 119.1(9) . . ?
C3 C2 H2B 120.4 . . ?
C1 C2 H2B 120.4 . . ?
C2 C3 C4 119.9(9) . . ?
C2 C3 H3B 120.0 . . ?
C4 C3 H3B 120.0 . . ?
C3 C4 C5 118.1(8) . . ?
C3 C4 N2 118.3(7) . . ?
C5 C4 N2 123.5(7) . . ?
N1 C5 C4 122.7(7) . . ?
N1 C5 H5A 118.7 . . ?
C4 C5 H5A 118.7 . . ?
O1 C6 N2 123.4(8) . . ?
O1 C6 C7 121.6(7) . . ?
N2 C6 C7 114.9(7) . . ?
C8 C7 C6 108.4(6) . . ?
C8 C7 H7A 110.0 . . ?
C6 C7 H7A 110.0 . . ?
C8 C7 H7B 110.0 . . ?
C6 C7 H7B 110.0 . . ?
H7A C7 H7B 108.4 . . ?
C9 C8 C13 118.7(6) . . ?
C9 C8 C7 120.8(6) . . ?
C13 C8 C7 120.4(6) . . ?
C8 C9 C10 120.3(7) . . ?
C8 C9 H9A 119.9 . . ?
C10 C9 H9A 119.9 . . ?
C11 C10 C9 121.5(7) . . ?
C11 C10 H10A 119.3 . . ?
C9 C10 H10A 119.3 . . ?
C10 C11 C12 119.2(7) . . ?
C10 C11 H11A 120.4 . . ?
C12 C11 H11A 120.4 . . ?
C11 C12 C13 119.5(6) . . ?
C11 C12 C14 120.6(7) . . ?
C13 C12 C14 119.9(7) . . ?
C8 C13 C12 120.9(7) . . ?
C8 C13 H13A 119.6 . . ?
C12 C13 H13A 119.6 . . ?
C15 C14 C12 113.8(6) . . ?
C15 C14 H14A 108.8 . . ?
C12 C14 H14A 108.8 . . ?
C15 C14 H14B 108.8 . . ?
C12 C14 H14B 108.8 . . ?
H14A C14 H14B 107.7 . . ?
O2 C15 N3 122.8(6) . . ?
O2 C15 C14 123.6(6) . . ?
N3 C15 C14 113.5(6) . . ?
C20 C16 N3 117.9(6) . . ?
C20 C16 C17 116.8(7) . . ?
N3 C16 C17 125.3(5) . . ?
C18 C17 C16 118.4(6) . . ?
C18 C17 H17A 120.8 . . ?
C16 C17 H17A 120.8 . . ?
C19 C18 C17 120.7(7) . . ?
C19 C18 H18A 119.7 . . ?
C17 C18 H18A 119.7 . . ?
N4 C19 C18 121.9(7) . . ?
N4 C19 H19A 119.0 . . ?
C18 C19 H19A 119.0 . . ?
N4 C20 C16 124.3(7) . . ?
N4 C20 H20A 117.8 . . ?
C16 C20 H20A 117.8 . . ?
C22 C21 H21A 109.5 . . ?
C22 C21 H21B 109.5 . . ?
H21A C21 H21B 109.5 . . ?
C22 C21 H21C 109.5 . . ?
H21A C21 H21C 109.5 . . ?
H21B C21 H21C 109.5 . . ?
N5 C22 C21 178.3(10) . . ?

_refine_diff_density_max         0.981
_refine_diff_density_min         -0.862
_refine_diff_density_rms         0.128

