# Electronic Supplementary Material (ESI) for CrystEngComm.
# This journal is © The Royal Society of Chemistry 2021

####################################################################### 
# 
# 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_ASZN18z33
_database_code_depnum_ccdc_archive 'CCDC 1959464'
loop_
_audit_author_name
_audit_author_address
'Allen Oliver'
;University of Notre Dame
United States of America
;
_audit_update_record             
;
2019-10-15 deposited with the CCDC.	2021-07-26 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         'C10 H8 Hg I2 N4 O'
_chemical_formula_sum            'C10 H8 Hg I2 N4 O'
_chemical_formula_weight         654.59

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                   4.9280(3)
_cell_length_b                   17.0736(11)
_cell_length_c                   16.5670(11)
_cell_angle_alpha                90
_cell_angle_beta                 91.6910(10)
_cell_angle_gamma                90
_cell_volume                     1393.32(15)
_cell_formula_units_Z            4
_cell_measurement_temperature    120(2)
_cell_measurement_reflns_used    9980
_cell_measurement_theta_min      2.39
_cell_measurement_theta_max      31.12
_exptl_crystal_description       block
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    3.121
_exptl_crystal_F_000             1160
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.222
_exptl_crystal_size_mid          0.116
_exptl_crystal_size_min          0.098
_exptl_absorpt_coefficient_mu    15.471
_shelx_estimated_absorpt_T_min   0.131
_shelx_estimated_absorpt_T_max   0.312
_exptl_absorpt_correction_type   numerical
_exptl_absorpt_correction_T_min  0.0897
_exptl_absorpt_correction_T_max  0.2708
_exptl_absorpt_process_details   'SADABS (Krause et al., 2015)'
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      120(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            24794
_diffrn_reflns_av_unetI/netI     0.0196
_diffrn_reflns_av_R_equivalents  0.0282
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_k_min       -24
_diffrn_reflns_limit_k_max       24
_diffrn_reflns_limit_l_min       -24
_diffrn_reflns_limit_l_max       24
_diffrn_reflns_theta_min         1.713
_diffrn_reflns_theta_max         31.406
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.945
_diffrn_measured_fraction_theta_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.945
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.945
_diffrn_reflns_point_group_measured_fraction_full 1.000
_reflns_number_total             4346
_reflns_number_gt                4005
_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 (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)+(0.0068P)²+2.0264P] 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         4346
_refine_ls_number_parameters     163
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0205
_refine_ls_R_factor_gt           0.0171
_refine_ls_wR_factor_ref         0.0322
_refine_ls_wR_factor_gt          0.0315
_refine_ls_goodness_of_fit_ref   1.115
_refine_ls_restrained_S_all      1.115
_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_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
C1 C 1.4503(5) 1.05354(16) 0.74724(15) 0.0142(5) Uani 1 1 d . . . . .
H1 H 1.4572 1.0897 0.7909 0.017 Uiso 1 1 calc R U . . .
C2 C 1.6022(6) 1.00976(16) 0.62623(16) 0.0170(5) Uani 1 1 d . . . . .
H2 H 1.7200 1.0144 0.5821 0.020 Uiso 1 1 calc R U . . .
C3 C 1.4214(6) 0.94752(17) 0.62823(17) 0.0198(6) Uani 1 1 d . . . . .
H3 H 1.4186 0.9105 0.5854 0.024 Uiso 1 1 calc R U . . .
C4 C 1.2693(5) 0.99064(15) 0.74852(15) 0.0126(5) Uani 1 1 d . . . . .
C5 C 1.0904(5) 0.97803(16) 0.81935(16) 0.0148(5) Uani 1 1 d . . . . .
C6 C 0.7377(5) 0.88539(15) 0.86477(15) 0.0131(5) Uani 1 1 d . . . . .
C7 C 0.7273(6) 0.90935(17) 0.94503(16) 0.0194(6) Uani 1 1 d . . . . .
H7 H 0.8432 0.9496 0.9655 0.023 Uiso 1 1 calc R U . . .
C8 C 0.5428(6) 0.87275(18) 0.99415(17) 0.0223(6) Uani 1 1 d . . . . .
H8 H 0.5311 0.8878 1.0492 0.027 Uiso 1 1 calc R U . . .
C9 C 0.3762(6) 0.81446(17) 0.96299(16) 0.0184(5) Uani 1 1 d . . . . .
H9 H 0.2513 0.7898 0.9974 0.022 Uiso 1 1 calc R U . . .
C10 C 0.5601(5) 0.82668(15) 0.83747(15) 0.0125(5) Uani 1 1 d . . . . .
H10 H 0.5638 0.8111 0.7825 0.015 Uiso 1 1 calc R U . . .
N1 N 1.6142(5) 1.06329(13) 0.68495(13) 0.0148(4) Uani 1 1 d . . . . .
N2 N 1.2518(5) 0.93826(14) 0.68856(14) 0.0171(5) Uani 1 1 d . . . . .
N3 N 0.9183(4) 0.91631(13) 0.80851(13) 0.0145(4) Uani 1 1 d . . . . .
H3N H 0.9199 0.8931 0.7611 0.017 Uiso 1 1 calc R U . . .
O1 O 1.1077(5) 1.01975(12) 0.87901(12) 0.0231(5) Uani 1 1 d . . . . .
N4 N 0.3853(5) 0.79169(13) 0.88589(13) 0.0135(4) Uani 1 1 d . . . . .
I1 I 0.04245(4) 0.72599(2) 0.68102(2) 0.01837(4) Uani 1 1 d . . . . .
I2 I -0.11435(4) 0.64292(2) 0.97367(2) 0.01720(4) Uani 1 1 d . . . . .
Hg1 Hg 0.09332(2) 0.68655(2) 0.83495(2) 0.01375(3) Uani 1 1 d . . . . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
C1 N1 1.340(3) . ?
C1 C4 1.397(4) . ?
C2 N1 1.335(3) . ?
C2 C3 1.388(4) . ?
C3 N2 1.331(3) . ?
C4 N2 1.338(3) . ?
C4 C5 1.504(4) . ?
C5 O1 1.219(3) . ?
C5 N3 1.361(3) . ?
C6 C7 1.394(4) . ?
C6 C10 1.397(4) . ?
C6 N3 1.410(3) . ?
C7 C8 1.387(4) . ?
C8 C9 1.381(4) . ?
C9 N4 1.337(3) . ?
C10 N4 1.335(3) . ?
N1 Hg1 2.577(2) 2_756 ?
N4 Hg1 2.436(2) . ?
I1 Hg1 2.6423(2) . ?
I2 Hg1 2.6500(2) . ?
Hg1 N1 2.577(2) 2_746 ?

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 C4 120.5(2) . . ?
N1 C2 C3 121.4(2) . . ?
N2 C3 C2 121.8(3) . . ?
N2 C4 C1 122.0(2) . . ?
N2 C4 C5 117.2(2) . . ?
C1 C4 C5 120.8(2) . . ?
O1 C5 N3 126.0(2) . . ?
O1 C5 C4 121.4(2) . . ?
N3 C5 C4 112.7(2) . . ?
C7 C6 C10 118.6(2) . . ?
C7 C6 N3 124.2(2) . . ?
C10 C6 N3 117.1(2) . . ?
C8 C7 C6 118.1(3) . . ?
C9 C8 C7 119.9(3) . . ?
N4 C9 C8 122.0(3) . . ?
N4 C10 C6 122.4(2) . . ?
C2 N1 C1 117.5(2) . . ?
C2 N1 Hg1 118.61(17) . 2_756 ?
C1 N1 Hg1 123.52(18) . 2_756 ?
C3 N2 C4 116.8(2) . . ?
C5 N3 C6 127.3(2) . . ?
C10 N4 C9 119.0(2) . . ?
C10 N4 Hg1 120.43(17) . . ?
C9 N4 Hg1 120.60(18) . . ?
N4 Hg1 N1 108.62(8) . 2_746 ?
N4 Hg1 I1 100.65(5) . . ?
N1 Hg1 I1 97.01(5) 2_746 . ?
N4 Hg1 I2 98.40(5) . . ?
N1 Hg1 I2 96.49(5) 2_746 . ?
I1 Hg1 I2 151.708(8) . . ?

_refine_diff_density_max         0.625
_refine_diff_density_min         -0.753
_refine_diff_density_rms         0.134

####################################################################### 
# 
# 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_aszn36
_database_code_depnum_ccdc_archive 'CCDC 1960183'
loop_
_audit_author_name
_audit_author_address
'Allen Oliver'
;University of Notre Dame
United States of America
;
_audit_update_record             
;
2019-10-18 deposited with the CCDC.	2021-07-26 downloaded from the CCDC.
;

_vrf_PLAT934_aszn36              
;
RESPONSE: The LSTing file shows no outliers with su/error > 10. PLATON 
is simply being overly aggressive in its interpretation of outlier
reflections. These higher than usual intensities are likely due to the
small amount of twinning present in the crystal.
;

_audit_creation_method           SHELXL-2018/3
_shelx_SHELXL_version_number     2018/3
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C20 H16 Cd I2 N8 O2'
_chemical_formula_sum            'C20 H16 Cd I2 N8 O2'
_chemical_formula_weight         766.61

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'
Cd Cd -0.8075 1.2024 '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'

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

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

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

_cell_length_a                   19.052(2)
_cell_length_b                   59.023(7)
_cell_length_c                   4.0392(5)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     4542.0(10)
_cell_formula_units_Z            8
_cell_measurement_temperature    120(2)
_cell_measurement_reflns_used    9961
_cell_measurement_theta_min      2.25
_cell_measurement_theta_max      28.46

_exptl_crystal_description       rod
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    2.242
_exptl_crystal_F_000             2896
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.201
_exptl_crystal_size_mid          0.158
_exptl_crystal_size_min          0.142
_exptl_absorpt_coefficient_mu    3.717
_shelx_estimated_absorpt_T_min   0.522
_shelx_estimated_absorpt_T_max   0.620
_exptl_absorpt_correction_type   numerical
_exptl_absorpt_correction_T_min  0.3924
_exptl_absorpt_correction_T_max  0.5055
_exptl_absorpt_process_details   'SADABS (Krause et al., 2015)'
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      120(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 8.33
_diffrn_reflns_number            22343
_diffrn_reflns_av_unetI/netI     0.0138
_diffrn_reflns_av_R_equivalents  0.0235
_diffrn_reflns_limit_h_min       -25
_diffrn_reflns_limit_h_max       25
_diffrn_reflns_limit_k_min       -78
_diffrn_reflns_limit_k_max       78
_diffrn_reflns_limit_l_min       -5
_diffrn_reflns_limit_l_max       5
_diffrn_reflns_theta_min         2.247
_diffrn_reflns_theta_max         28.462
_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 0.998
_diffrn_reflns_point_group_measured_fraction_full 0.999
_reflns_number_total             2871
_reflns_number_gt                2815
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.756
_reflns_Friedel_fraction_max     0.997
_reflns_Friedel_fraction_full    0.999

_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences. Completness statistics refer to single and
 composite reflections containing twin component 1 only.
;

_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-2018/3 (Sheldrick, 2018)'
_computing_molecular_graphics    ?
_computing_publication_material  ?
_refine_special_details          
;
 Refined as a 2-component inversion twin.
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+99.6890P] 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_abs_structure_details 
;
 Refined as an inversion twin. Twin occupancy was refined to
0.92:0.08
;
_refine_ls_abs_structure_Flack   0.07(5)
_chemical_absolute_configuration ad
_refine_ls_number_reflns         2871
_refine_ls_number_parameters     151
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0250
_refine_ls_R_factor_gt           0.0244
_refine_ls_wR_factor_ref         0.0656
_refine_ls_wR_factor_gt          0.0655
_refine_ls_goodness_of_fit_ref   1.467
_refine_ls_restrained_S_all      1.467
_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
Cd1 Cd 0.250000 0.250000 0.1864(2) 0.01089(14) Uani 1 2 d S T P . .
I1 I 0.31503(2) 0.21975(2) -0.31534(11) 0.01232(10) Uani 1 1 d . . . . .
O1 O 0.2025(3) 0.16471(10) -0.1685(16) 0.0246(14) Uani 1 1 d . . . . .
N1 N 0.1485(3) 0.22666(9) 0.184(2) 0.0121(10) Uani 1 1 d . . . . .
N2 N 0.0993(3) 0.16652(10) 0.1195(15) 0.0131(14) Uani 1 1 d . . . . .
H2 H 0.065645 0.158301 0.208283 0.016 Uiso 1 1 calc R U . . .
N3 N 0.1984(4) 0.09504(12) -0.2117(18) 0.0205(15) Uani 1 1 d . . . . .
N4 N 0.0905(3) 0.11998(11) 0.0953(17) 0.0160(14) Uani 1 1 d . . . . .
C1 C 0.1536(4) 0.20408(11) 0.158(2) 0.0115(13) Uani 1 1 d . . . . .
H1 H 0.198786 0.197290 0.148169 0.014 Uiso 1 1 calc R U . . .
C2 C 0.0940(4) 0.19029(12) 0.147(2) 0.0118(14) Uani 1 1 d . . . . .
C3 C 0.0280(3) 0.20021(11) 0.177(3) 0.0141(13) Uani 1 1 d . . . . .
H3 H -0.013191 0.191140 0.176699 0.017 Uiso 1 1 calc R U . . .
C4 C 0.0235(3) 0.22362(11) 0.207(3) 0.0157(14) Uani 1 1 d . . . . .
H4 H -0.020906 0.230850 0.225252 0.019 Uiso 1 1 calc R U . . .
C5 C 0.0847(4) 0.23620(11) 0.209(2) 0.0125(13) Uani 1 1 d . . . . .
H5 H 0.081497 0.252197 0.230089 0.015 Uiso 1 1 calc R U . . .
C6 C 0.1527(4) 0.15538(12) -0.034(2) 0.0153(15) Uani 1 1 d . . . . .
C7 C 0.1463(4) 0.12993(12) -0.041(3) 0.0148(14) Uani 1 1 d . . . . .
C8 C 0.1998(4) 0.11776(14) -0.194(2) 0.0198(17) Uani 1 1 d . . . . .
H8 H 0.238269 0.125720 -0.288841 0.024 Uiso 1 1 calc R U . . .
C9 C 0.1424(4) 0.08513(12) -0.076(3) 0.0193(14) Uani 1 1 d . . . . .
H9 H 0.138771 0.069086 -0.083494 0.023 Uiso 1 1 calc R U . . .
C10 C 0.0896(4) 0.09726(14) 0.076(2) 0.0179(16) Uani 1 1 d . . . . .
H10 H 0.051186 0.089270 0.169796 0.021 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
Cd1 N1 2.374(5) 14 ?
Cd1 N1 2.374(5) . ?
Cd1 I1 2.9618(8) 14_556 ?
Cd1 I1 2.9618(8) 1_556 ?
Cd1 I1 2.9716(8) 14 ?
Cd1 I1 2.9716(8) . ?
O1 C6 1.224(10) . ?
N1 C1 1.340(8) . ?
N1 C5 1.344(8) . ?
N2 C6 1.360(10) . ?
N2 C2 1.411(9) . ?
N3 C9 1.336(11) . ?
N3 C8 1.343(11) . ?
N4 C7 1.334(10) . ?
N4 C10 1.344(10) . ?
C1 C2 1.399(9) . ?
C2 C3 1.392(9) . ?
C3 C4 1.390(9) . ?
C4 C5 1.382(9) . ?
C6 C7 1.507(9) . ?
C7 C8 1.392(11) . ?
C9 C10 1.377(12) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
N1 Cd1 N1 179.5(5) 14 . ?
N1 Cd1 I1 89.66(18) 14 14_556 ?
N1 Cd1 I1 90.70(18) . 14_556 ?
N1 Cd1 I1 90.70(18) 14 1_556 ?
N1 Cd1 I1 89.66(18) . 1_556 ?
I1 Cd1 I1 94.40(3) 14_556 1_556 ?
N1 Cd1 I1 89.30(18) 14 14 ?
N1 Cd1 I1 90.33(18) . 14 ?
I1 Cd1 I1 85.805(14) 14_556 14 ?
I1 Cd1 I1 179.80(3) 1_556 14 ?
N1 Cd1 I1 90.33(18) 14 . ?
N1 Cd1 I1 89.30(18) . . ?
I1 Cd1 I1 179.80(3) 14_556 . ?
I1 Cd1 I1 85.804(14) 1_556 . ?
I1 Cd1 I1 93.99(3) 14 . ?
Cd1 I1 Cd1 85.803(14) 1_554 . ?
C1 N1 C5 119.2(6) . . ?
C1 N1 Cd1 121.2(4) . . ?
C5 N1 Cd1 119.6(4) . . ?
C6 N2 C2 124.7(7) . . ?
C9 N3 C8 115.6(7) . . ?
C7 N4 C10 115.2(7) . . ?
N1 C1 C2 121.5(6) . . ?
C3 C2 C1 119.1(6) . . ?
C3 C2 N2 119.3(6) . . ?
C1 C2 N2 121.5(6) . . ?
C4 C3 C2 118.8(6) . . ?
C5 C4 C3 118.8(6) . . ?
N1 C5 C4 122.5(6) . . ?
O1 C6 N2 124.3(7) . . ?
O1 C6 C7 120.1(7) . . ?
N2 C6 C7 115.5(7) . . ?
N4 C7 C8 122.7(7) . . ?
N4 C7 C6 119.6(7) . . ?
C8 C7 C6 117.7(7) . . ?
N3 C8 C7 121.6(7) . . ?
N3 C9 C10 122.6(7) . . ?
N4 C10 C9 122.4(8) . . ?

_refine_diff_density_max         1.289
_refine_diff_density_min         -1.251
_refine_diff_density_rms         0.154

####################################################################### 
# 
# 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_umi1712
_database_code_depnum_ccdc_archive 'CCDC 1960181'
loop_
_audit_author_name
_audit_author_address
'Allen Oliver'
;University of Notre Dame
United States of America
;
_audit_update_record             
;
2019-10-18 deposited with the CCDC.	2021-07-26 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         'C10 H8 Br2 Hg N4 O'
_chemical_formula_sum            'C10 H8 Br2 Hg N4 O'
_chemical_formula_weight         560.61

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'

_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 21/n'
_space_group_name_Hall           '-P 2yn'

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

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

_cell_length_a                   3.9055(4)
_cell_length_b                   34.576(3)
_cell_length_c                   9.6848(9)
_cell_angle_alpha                90
_cell_angle_beta                 101.4160(10)
_cell_angle_gamma                90
_cell_volume                     1281.9(2)
_cell_formula_units_Z            4
_cell_measurement_temperature    120(2)
_cell_measurement_reflns_used    8005
_cell_measurement_theta_min      2.23
_cell_measurement_theta_max      28.32

_exptl_crystal_description       rod
_exptl_crystal_colour            colorless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    2.905
_exptl_crystal_F_000             1016
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.398
_exptl_crystal_size_mid          0.048
_exptl_crystal_size_min          0.031
_exptl_absorpt_coefficient_mu    18.232
_shelx_estimated_absorpt_T_min   0.052
_shelx_estimated_absorpt_T_max   0.602
_exptl_absorpt_correction_type   numerical
_exptl_absorpt_correction_T_min  0.0571
_exptl_absorpt_correction_T_max  0.6843
_exptl_absorpt_process_details   'SADABS (Krause et al., 2015)'
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      120(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  'Bruker APEX-II'
_diffrn_ambient_temperature_diffrn_measurement_method 
'combination of \w and \f-scans '
_diffrn_detector_area_resol_mean 8.33
_diffrn_reflns_number            24690
_diffrn_reflns_av_unetI/netI     0.0273
_diffrn_reflns_av_R_equivalents  0.0473
_diffrn_reflns_limit_h_min       -5
_diffrn_reflns_limit_h_max       5
_diffrn_reflns_limit_k_min       -46
_diffrn_reflns_limit_k_max       46
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_theta_min         2.225
_diffrn_reflns_theta_max         28.384
_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             3210
_reflns_number_gt                2945
_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.

Reflection 0 2 0 was found to have a zero intensity and was omitted
from the data.
;

_computing_data_collection       'Bruker APEX-3 (Bruker, 2015)'
_computing_cell_refinement       'Bruker SAINT (Bruker, 2015)'
_computing_data_reduction        'Bruker SAINT (Bruker, 2015)'
_computing_structure_solution    'SHELXT-2014/2 (Sheldrick, 2015)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2015)'
_computing_molecular_graphics    'Bruker XP (Bruker, 2015)'
_computing_publication_material  'CIFTAB (Sheldrick, 2008)'

_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)+(0.0054P)²+4.1597P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         3210
_refine_ls_number_parameters     167
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0299
_refine_ls_R_factor_gt           0.0250
_refine_ls_wR_factor_ref         0.0431
_refine_ls_wR_factor_gt          0.0421
_refine_ls_goodness_of_fit_ref   1.153
_refine_ls_restrained_S_all      1.153
_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
Hg1 Hg 0.63123(4) 0.44760(2) 0.87209(2) 0.01468(5) Uani 1 1 d . . . . .
Br1 Br 0.20058(10) 0.50082(2) 0.80428(5) 0.01616(9) Uani 1 1 d . . . . .
Br2 Br 1.06865(10) 0.40216(2) 1.00600(4) 0.01573(9) Uani 1 1 d . . . . .
O1 O 0.9092(8) 0.32342(9) 0.2783(3) 0.0191(7) Uani 1 1 d . . . . .
N1 N 0.7477(9) 0.32344(11) 0.4929(4) 0.0137(7) Uani 1 1 d . . . . .
H1N H 0.733(12) 0.3102(14) 0.559(5) 0.013(13) Uiso 1 1 d . . . . .
N2 N 0.8244(9) 0.24430(10) 0.5040(4) 0.0133(7) Uani 1 1 d . . . . .
N3 N 1.0458(9) 0.20539(10) 0.2811(4) 0.0163(8) Uani 1 1 d . . . . .
N4 N 0.5742(9) 0.41685(10) 0.6432(4) 0.0135(7) Uani 1 1 d . . . . .
C1 C 0.8540(10) 0.30626(12) 0.3828(4) 0.0126(8) Uani 1 1 d . . . . .
C2 C 0.8990(10) 0.26299(12) 0.3919(4) 0.0112(8) Uani 1 1 d . . . . .
C3 C 1.0072(10) 0.24392(13) 0.2830(5) 0.0146(9) Uani 1 1 d . . . . .
H3 H 1.0563 0.2586 0.2063 0.018 Uiso 1 1 calc R U . . .
C4 C 0.9729(11) 0.18672(13) 0.3930(5) 0.0161(9) Uani 1 1 d . . . . .
H4 H 0.9981 0.1594 0.3978 0.019 Uiso 1 1 calc R U . . .
C5 C 0.8623(11) 0.20584(12) 0.5018(5) 0.0152(9) Uani 1 1 d . . . . .
H5 H 0.8112 0.1911 0.5780 0.018 Uiso 1 1 calc R U . . .
C6 C 0.6526(10) 0.36282(12) 0.4975(4) 0.0125(8) Uani 1 1 d . . . . .
C7 C 0.6816(10) 0.38046(12) 0.6285(4) 0.0137(8) Uani 1 1 d . . . . .
H7 H 0.7810 0.3662 0.7105 0.016 Uiso 1 1 calc R U . . .
C9 C 0.4373(11) 0.43717(12) 0.5263(5) 0.0155(9) Uani 1 1 d . . . . .
H9 H 0.3580 0.4628 0.5360 0.019 Uiso 1 1 calc R U . . .
C10 C 0.4092(11) 0.42181(13) 0.3933(5) 0.0176(9) Uani 1 1 d . . . . .
H10 H 0.3178 0.4370 0.3128 0.021 Uiso 1 1 calc R U . . .
C11 C 0.5143(11) 0.38417(12) 0.3771(5) 0.0161(9) Uani 1 1 d . . . . .
H11 H 0.4927 0.3731 0.2860 0.019 Uiso 1 1 calc R U . . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Hg1 N4 2.429(3) . ?
Hg1 Br2 2.4884(4) . ?
Hg1 Br1 2.4917(5) . ?
Hg1 Br1 3.0561(5) 1_655 ?
Br1 Hg1 3.0561(5) 1_455 ?
O1 C1 1.228(5) . ?
N1 C1 1.355(5) . ?
N1 C6 1.415(5) . ?
N1 H1N 0.80(5) . ?
N2 C5 1.338(5) . ?
N2 C2 1.344(5) . ?
N3 C4 1.339(6) . ?
N3 C3 1.341(5) . ?
N4 C7 1.343(5) . ?
N4 C9 1.350(5) . ?
C1 C2 1.507(6) . ?
C2 C3 1.380(6) . ?
C3 H3 0.9500 . ?
C4 C5 1.384(6) . ?
C4 H4 0.9500 . ?
C5 H5 0.9500 . ?
C6 C7 1.392(6) . ?
C6 C11 1.395(6) . ?
C7 H7 0.9500 . ?
C9 C10 1.378(6) . ?
C9 H9 0.9500 . ?
C10 C11 1.383(6) . ?
C10 H10 0.9500 . ?
C11 H11 0.9500 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
N4 Hg1 Br2 97.39(8) . . ?
N4 Hg1 Br1 98.49(8) . . ?
Br2 Hg1 Br1 164.073(16) . . ?
N4 Hg1 Br1 90.38(9) . 1_655 ?
Br2 Hg1 Br1 92.207(15) . 1_655 ?
Br1 Hg1 Br1 88.889(15) . 1_655 ?
Hg1 Br1 Hg1 88.889(15) . 1_455 ?
C1 N1 C6 124.7(4) . . ?
C1 N1 H1N 118(4) . . ?
C6 N1 H1N 118(4) . . ?
C5 N2 C2 115.0(4) . . ?
C4 N3 C3 115.2(4) . . ?
C7 N4 C9 118.6(4) . . ?
C7 N4 Hg1 122.2(3) . . ?
C9 N4 Hg1 119.2(3) . . ?
O1 C1 N1 124.6(4) . . ?
O1 C1 C2 119.3(4) . . ?
N1 C1 C2 116.1(4) . . ?
N2 C2 C3 122.4(4) . . ?
N2 C2 C1 118.9(4) . . ?
C3 C2 C1 118.7(4) . . ?
N3 C3 C2 122.5(4) . . ?
N3 C3 H3 118.8 . . ?
C2 C3 H3 118.8 . . ?
N3 C4 C5 122.3(4) . . ?
N3 C4 H4 118.9 . . ?
C5 C4 H4 118.9 . . ?
N2 C5 C4 122.6(4) . . ?
N2 C5 H5 118.7 . . ?
C4 C5 H5 118.7 . . ?
C7 C6 C11 118.5(4) . . ?
C7 C6 N1 118.4(4) . . ?
C11 C6 N1 123.0(4) . . ?
N4 C7 C6 122.4(4) . . ?
N4 C7 H7 118.8 . . ?
C6 C7 H7 118.8 . . ?
N4 C9 C10 121.9(4) . . ?
N4 C9 H9 119.0 . . ?
C10 C9 H9 119.0 . . ?
C9 C10 C11 119.9(4) . . ?
C9 C10 H10 120.1 . . ?
C11 C10 H10 120.1 . . ?
C10 C11 C6 118.6(4) . . ?
C10 C11 H11 120.7 . . ?
C6 C11 H11 120.7 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C6 N1 C1 O1 6.4(7) . . . . ?
C6 N1 C1 C2 -172.5(4) . . . . ?
C5 N2 C2 C3 -0.2(6) . . . . ?
C5 N2 C2 C1 178.2(3) . . . . ?
O1 C1 C2 N2 -177.4(4) . . . . ?
N1 C1 C2 N2 1.6(5) . . . . ?
O1 C1 C2 C3 1.1(6) . . . . ?
N1 C1 C2 C3 -179.9(4) . . . . ?
C4 N3 C3 C2 -0.3(6) . . . . ?
N2 C2 C3 N3 0.0(6) . . . . ?
C1 C2 C3 N3 -178.4(4) . . . . ?
C3 N3 C4 C5 0.7(6) . . . . ?
C2 N2 C5 C4 0.6(6) . . . . ?
N3 C4 C5 N2 -0.9(7) . . . . ?
C1 N1 C6 C7 -155.1(4) . . . . ?
C1 N1 C6 C11 28.4(6) . . . . ?
C9 N4 C7 C6 -0.9(6) . . . . ?
Hg1 N4 C7 C6 -179.4(3) . . . . ?
C11 C6 C7 N4 1.5(6) . . . . ?
N1 C6 C7 N4 -175.2(4) . . . . ?
C7 N4 C9 C10 -0.8(6) . . . . ?
Hg1 N4 C9 C10 177.7(3) . . . . ?
N4 C9 C10 C11 1.8(7) . . . . ?
C9 C10 C11 C6 -1.0(6) . . . . ?
C7 C6 C11 C10 -0.5(6) . . . . ?
N1 C6 C11 C10 176.0(4) . . . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
N1 H1N N3 0.80(5) 2.46(5) 3.206(5) 155(4) 4_566
C3 H3 N2 0.95 2.40 3.213(6) 143.4 4_665
C4 H4 Br2 0.95 3.02 3.717(4) 131.2 4_565
C7 H7 Br2 0.95 3.12 3.745(4) 125.1 .
C9 H9 Br1 0.95 3.08 3.733(4) 127.3 .
C11 H11 Br2 0.95 3.05 3.722(4) 128.7 1_454
C11 H11 O1 0.95 2.38 2.879(5) 112.6 .

_refine_diff_density_max         1.068
_refine_diff_density_min         -1.076
_refine_diff_density_rms         0.159

####################################################################### 
# 
# 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_umi1714
_database_code_depnum_ccdc_archive 'CCDC 1960180'
loop_
_audit_author_name
_audit_author_address
'Allen Oliver'
;University of Notre Dame
United States of America
;
_audit_update_record             
;
2019-10-18 deposited with the CCDC.	2021-07-26 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         'C10 H8 Cl2 Hg N4 O'
_chemical_formula_sum            'C10 H8 Cl2 Hg N4 O'
_chemical_formula_weight         471.69

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
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      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                   3.8092(4)
_cell_length_b                   33.691(4)
_cell_length_c                   9.6053(11)
_cell_angle_alpha                90
_cell_angle_beta                 100.5337(15)
_cell_angle_gamma                90
_cell_volume                     1211.9(2)
_cell_formula_units_Z            4
_cell_measurement_temperature    120(2)
_cell_measurement_reflns_used    8595
_cell_measurement_theta_min      2.24
_cell_measurement_theta_max      28.35

_exptl_crystal_description       rod
_exptl_crystal_colour            colorless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    2.585
_exptl_crystal_F_000             872
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.406
_exptl_crystal_size_mid          0.049
_exptl_crystal_size_min          0.029
_exptl_absorpt_coefficient_mu    13.132
_shelx_estimated_absorpt_T_min   0.076
_shelx_estimated_absorpt_T_max   0.702
_exptl_absorpt_correction_type   numerical
_exptl_absorpt_correction_T_min  0.0891
_exptl_absorpt_correction_T_max  0.7480
_exptl_absorpt_process_details   'SADABS (Krause et al., 2015)'
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      120(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  'Bruker APEX-II'
_diffrn_measurement_method       'combination of ω and φ-scans '
_diffrn_detector_area_resol_mean 8.33
_diffrn_reflns_number            23170
_diffrn_reflns_av_unetI/netI     0.0243
_diffrn_reflns_av_R_equivalents  0.0423
_diffrn_reflns_limit_h_min       -5
_diffrn_reflns_limit_h_max       5
_diffrn_reflns_limit_k_min       -44
_diffrn_reflns_limit_k_max       45
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_theta_min         2.240
_diffrn_reflns_theta_max         28.392
_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             3019
_reflns_number_gt                2746
_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.

Refelction [0 2 0] was eclipsed by the beamstop and was omitted 
from the data for the model.
;

_computing_data_collection       'Bruker APEX-3 (Bruker, 2015)'
_computing_cell_refinement       'Bruker SAINT (Bruker, 2015)'
_computing_data_reduction        'Bruker SAINT (Bruker, 2015)'
_computing_structure_solution    'SHELXT-2014/2 (Sheldrick, 2015)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2015)'
_computing_molecular_graphics    'Bruker XP (Bruker, 2015)'
_computing_publication_material  'CIFTAB (Sheldrick, 2008)'
_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)+(0.0096P)²+3.1601P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   direct
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         3019
_refine_ls_number_parameters     167
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0272
_refine_ls_R_factor_gt           0.0224
_refine_ls_wR_factor_ref         0.0407
_refine_ls_wR_factor_gt          0.0395
_refine_ls_goodness_of_fit_ref   1.120
_refine_ls_restrained_S_all      1.120
_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
Hg1 Hg 0.24974(3) 0.44936(2) 0.11322(2) 0.01363(4) Uani 1 1 d . . . . .
Cl1 Cl 0.5781(2) 0.40478(3) -0.00466(10) 0.01629(18) Uani 1 1 d . . . . .
Cl2 Cl -0.1120(2) 0.50077(3) 0.18109(10) 0.01518(18) Uani 1 1 d . . . . .
O1 O 1.1203(7) 0.32512(8) 0.7190(3) 0.0160(6) Uani 1 1 d . . . . .
N1 N 0.4195(8) 0.42007(9) 0.3472(3) 0.0147(6) Uani 1 1 d . . . . .
N2 N 0.7461(8) 0.32536(9) 0.5041(3) 0.0130(6) Uani 1 1 d . . . . .
H2N H 0.668(11) 0.3097(13) 0.439(5) 0.014(11) Uiso 1 1 d . . . . .
N3 N 0.8088(8) 0.24408(9) 0.4934(3) 0.0132(6) Uani 1 1 d . . . . .
N4 N 1.2502(8) 0.20401(9) 0.7163(3) 0.0143(6) Uani 1 1 d . . . . .
C1 C 0.5477(9) 0.38289(11) 0.3655(4) 0.0112(7) Uani 1 1 d . . . . .
H1 H 0.5720 0.3677 0.2844 0.013 Uiso 1 1 calc R U . . .
C2 C 0.6456(9) 0.36585(11) 0.4978(4) 0.0114(7) Uani 1 1 d . . . . .
C3 C 0.6258(10) 0.38809(11) 0.6170(4) 0.0148(8) Uani 1 1 d . . . . .
H3 H 0.6955 0.3772 0.7091 0.018 Uiso 1 1 calc R U . . .
C4 C 0.5011(10) 0.42682(12) 0.5983(4) 0.0168(8) Uani 1 1 d . . . . .
H4 H 0.4884 0.4431 0.6781 0.020 Uiso 1 1 calc R U . . .
C5 C 0.3961(10) 0.44151(11) 0.4633(4) 0.0157(8) Uani 1 1 d . . . . .
H5 H 0.3038 0.4677 0.4517 0.019 Uiso 1 1 calc R U . . .
C6 C 0.9607(9) 0.30757(11) 0.6149(4) 0.0121(7) Uani 1 1 d . . . . .
C7 C 0.9944(9) 0.26312(11) 0.6053(4) 0.0115(7) Uani 1 1 d . . . . .
C8 C 1.2096(9) 0.24344(11) 0.7154(4) 0.0129(7) Uani 1 1 d . . . . .
H8 H 1.3326 0.2584 0.7930 0.015 Uiso 1 1 calc R U . . .
C9 C 1.0673(9) 0.18486(11) 0.6044(4) 0.0159(8) Uani 1 1 d . . . . .
H9 H 1.0889 0.1568 0.5995 0.019 Uiso 1 1 calc R U . . .
C10 C 0.8451(9) 0.20469(11) 0.4944(4) 0.0149(8) Uani 1 1 d . . . . .
H10 H 0.7162 0.1897 0.4181 0.018 Uiso 1 1 calc R U . . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Hg1 Cl1 2.3708(9) . ?
Hg1 Cl2 2.3774(9) . ?
Hg1 N1 2.431(3) . ?
Hg1 Cl2 2.9592(9) 1_655 ?
Cl2 Hg1 2.9592(9) 1_455 ?
O1 C6 1.224(4) . ?
N1 C1 1.344(5) . ?
N1 C5 1.345(5) . ?
N2 C6 1.357(5) . ?
N2 C2 1.415(5) . ?
N2 H2N 0.83(4) . ?
N3 C10 1.334(5) . ?
N3 C7 1.337(5) . ?
N4 C9 1.335(5) . ?
N4 C8 1.337(5) . ?
C1 C2 1.382(5) . ?
C1 H1 0.9500 . ?
C2 C3 1.382(5) . ?
C3 C4 1.389(5) . ?
C3 H3 0.9500 . ?
C4 C5 1.378(5) . ?
C4 H4 0.9500 . ?
C5 H5 0.9500 . ?
C6 C7 1.508(5) . ?
C7 C8 1.383(5) . ?
C8 H8 0.9500 . ?
C9 C10 1.398(5) . ?
C9 H9 0.9500 . ?
C10 H10 0.9500 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
Cl1 Hg1 Cl2 167.26(3) . . ?
Cl1 Hg1 N1 96.31(8) . . ?
Cl2 Hg1 N1 96.42(8) . . ?
Cl1 Hg1 Cl2 89.54(3) . 1_655 ?
Cl2 Hg1 Cl2 90.41(3) . 1_655 ?
N1 Hg1 Cl2 88.00(7) . 1_655 ?
Hg1 Cl2 Hg1 90.41(3) . 1_455 ?
C1 N1 C5 118.0(3) . . ?
C1 N1 Hg1 121.9(2) . . ?
C5 N1 Hg1 120.1(2) . . ?
C6 N2 C2 125.4(3) . . ?
C6 N2 H2N 113(3) . . ?
C2 N2 H2N 121(3) . . ?
C10 N3 C7 115.6(3) . . ?
C9 N4 C8 115.6(3) . . ?
N1 C1 C2 122.5(3) . . ?
N1 C1 H1 118.7 . . ?
C2 C1 H1 118.7 . . ?
C1 C2 C3 119.4(3) . . ?
C1 C2 N2 117.7(3) . . ?
C3 C2 N2 122.8(3) . . ?
C2 C3 C4 118.1(3) . . ?
C2 C3 H3 120.9 . . ?
C4 C3 H3 120.9 . . ?
C5 C4 C3 119.5(4) . . ?
C5 C4 H4 120.2 . . ?
C3 C4 H4 120.2 . . ?
N1 C5 C4 122.4(3) . . ?
N1 C5 H5 118.8 . . ?
C4 C5 H5 118.8 . . ?
O1 C6 N2 124.4(4) . . ?
O1 C6 C7 119.7(3) . . ?
N2 C6 C7 115.9(3) . . ?
N3 C7 C8 122.5(3) . . ?
N3 C7 C6 119.2(3) . . ?
C8 C7 C6 118.3(3) . . ?
N4 C8 C7 122.2(3) . . ?
N4 C8 H8 118.9 . . ?
C7 C8 H8 118.9 . . ?
N4 C9 C10 122.2(3) . . ?
N4 C9 H9 118.9 . . ?
C10 C9 H9 118.9 . . ?
N3 C10 C9 121.9(3) . . ?
N3 C10 H10 119.0 . . ?
C9 C10 H10 119.0 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C5 N1 C1 C2 1.8(5) . . . . ?
Hg1 N1 C1 C2 179.9(2) . . . . ?
N1 C1 C2 C3 -2.7(5) . . . . ?
N1 C1 C2 N2 174.3(3) . . . . ?
C6 N2 C2 C1 155.7(3) . . . . ?
C6 N2 C2 C3 -27.5(5) . . . . ?
C1 C2 C3 C4 1.1(5) . . . . ?
N2 C2 C3 C4 -175.7(3) . . . . ?
C2 C3 C4 C5 1.2(5) . . . . ?
C1 N1 C5 C4 0.6(5) . . . . ?
Hg1 N1 C5 C4 -177.6(3) . . . . ?
C3 C4 C5 N1 -2.1(6) . . . . ?
C2 N2 C6 O1 -6.7(6) . . . . ?
C2 N2 C6 C7 172.8(3) . . . . ?
C10 N3 C7 C8 -0.2(5) . . . . ?
C10 N3 C7 C6 -178.2(3) . . . . ?
O1 C6 C7 N3 177.7(3) . . . . ?
N2 C6 C7 N3 -1.8(5) . . . . ?
O1 C6 C7 C8 -0.5(5) . . . . ?
N2 C6 C7 C8 -179.9(3) . . . . ?
C9 N4 C8 C7 -0.5(5) . . . . ?
N3 C7 C8 N4 1.0(6) . . . . ?
C6 C7 C8 N4 179.0(3) . . . . ?
C8 N4 C9 C10 -0.6(5) . . . . ?
C7 N3 C10 C9 -1.0(5) . . . . ?
N4 C9 C10 N3 1.4(6) . . . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
N2 H2N N3 0.83(4) 2.31(4) 2.752(5) 113(3) .
N2 H2N N4 0.83(4) 2.46(4) 3.207(4) 149(4) 4_465
C3 H3 O1 0.95 2.38 2.887(5) 113.3 .
C4 H4 Cl2 0.95 2.86 3.713(4) 150.1 3_566
C8 H8 N3 0.95 2.39 3.207(5) 143.6 4_666

_refine_diff_density_max         0.884
_refine_diff_density_min         -1.064
_refine_diff_density_rms         0.142

####################################################################### 
# 
# 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_umi1715
_database_code_depnum_ccdc_archive 'CCDC 1960182'
loop_
_audit_author_name
_audit_author_address
'Allen Oliver'
;University of Notre Dame
United States of America
;
_audit_update_record             
;
2019-10-18 deposited with the CCDC.	2021-07-26 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         'C20 H16 Cl2 N8 O2 Zn'
_chemical_formula_sum            'C20 H16 Cl2 N8 O2 Zn'
_chemical_formula_weight         536.68

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'
Zn Zn 0.2839 1.4301 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

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

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

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

_cell_length_a                   7.5409(7)
_cell_length_b                   11.8032(11)
_cell_length_c                   13.1436(13)
_cell_angle_alpha                79.8560(10)
_cell_angle_beta                 89.9800(10)
_cell_angle_gamma                74.4990(10)
_cell_volume                     1108.35(18)
_cell_formula_units_Z            2
_cell_measurement_temperature    120(2)
_cell_measurement_reflns_used    8896
_cell_measurement_theta_min      2.62
_cell_measurement_theta_max      28.33

_exptl_crystal_description       block
_exptl_crystal_colour            colorless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.608
_exptl_crystal_F_000             544
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.172
_exptl_crystal_size_mid          0.119
_exptl_crystal_size_min          0.114
_exptl_absorpt_coefficient_mu    1.385
_shelx_estimated_absorpt_T_min   0.797
_shelx_estimated_absorpt_T_max   0.858
_exptl_absorpt_correction_type   numerical
_exptl_absorpt_correction_T_min  0.2518
_exptl_absorpt_correction_T_max  0.3678
_exptl_absorpt_process_details   'SADABS (Krause et al., 2015)'
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      120(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  'Bruker APEX-II'
_diffrn_measurement_method       'combination of ω and φ-scans '
_diffrn_detector_area_resol_mean 8.33
_diffrn_reflns_number            21812
_diffrn_reflns_av_unetI/netI     0.0257
_diffrn_reflns_av_R_equivalents  0.0276
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_theta_min         1.576
_diffrn_reflns_theta_max         28.415
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measured_fraction_theta_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_point_group_measured_fraction_full 1.000
_reflns_number_total             5562
_reflns_number_gt                4874
_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 APEX-3 (Bruker, 2015)'
_computing_cell_refinement       'Bruker SAINT (Bruker, 2015)'
_computing_data_reduction        'Bruker SAINT (Bruker, 2015)'
_computing_structure_solution    'SHELXT-2014/2 (Sheldrick, 2015)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2015)'
_computing_molecular_graphics    'Bruker XP (Bruker, 2015)'
_computing_publication_material  'CIFTAB (Sheldrick, 2008)'
_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)+(0.0246P)²+0.5126P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         5562
_refine_ls_number_parameters     306
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0318
_refine_ls_R_factor_gt           0.0254
_refine_ls_wR_factor_ref         0.0601
_refine_ls_wR_factor_gt          0.0576
_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
Zn1 Zn 0.20978(2) 0.56326(2) 0.73496(2) 0.01478(5) Uani 1 1 d . . . . .
Cl1 Cl -0.00276(5) 0.73845(3) 0.72179(3) 0.02024(8) Uani 1 1 d . . . . .
Cl2 Cl 0.48933(5) 0.56705(4) 0.68414(3) 0.02216(9) Uani 1 1 d . . . . .
O1 O 0.2862(2) 0.11863(11) 0.90292(9) 0.0332(3) Uani 1 1 d . . . . .
O2 O 0.58921(15) 0.22083(10) 0.56814(9) 0.0225(2) Uani 1 1 d . . . . .
N1 N 0.22849(17) 0.48089(11) 0.88701(10) 0.0166(3) Uani 1 1 d . . . . .
N2 N 0.2320(2) 0.19328(12) 1.05273(10) 0.0204(3) Uani 1 1 d . . . . .
H2N H 0.212(3) 0.1736(17) 1.1124(15) 0.025(5) Uiso 1 1 d . . . . .
N3 N 0.2593(3) -0.21615(14) 1.06083(12) 0.0402(4) Uani 1 1 d . . . . .
N4 N 0.21451(19) -0.01738(12) 1.15661(10) 0.0202(3) Uani 1 1 d . . . . .
N5 N 0.12653(17) 0.44887(11) 0.65795(9) 0.0154(2) Uani 1 1 d . . . . .
N6 N 0.31380(18) 0.23347(12) 0.48733(10) 0.0169(3) Uani 1 1 d . . . . .
H6N H 0.268(3) 0.2147(17) 0.4356(15) 0.024(5) Uiso 1 1 d . . . . .
N7 N 0.86677(19) -0.01542(12) 0.38305(10) 0.0207(3) Uani 1 1 d . . . . .
N8 N 0.48934(19) 0.10143(12) 0.35233(10) 0.0216(3) Uani 1 1 d . . . . .
C1 C 0.2235(2) 0.36667(13) 0.91606(12) 0.0186(3) Uani 1 1 d . . . . .
H1 H 0.2054 0.3230 0.8646 0.022 Uiso 1 1 calc R U . . .
C2 C 0.2440(2) 0.31088(13) 1.01956(12) 0.0173(3) Uani 1 1 d . . . . .
C3 C 0.2771(2) 0.37441(14) 1.09412(12) 0.0198(3) Uani 1 1 d . . . . .
H3 H 0.2968 0.3376 1.1650 0.024 Uiso 1 1 calc R U . . .
C4 C 0.2808(2) 0.49141(14) 1.06329(12) 0.0219(3) Uani 1 1 d . . . . .
H4 H 0.3017 0.5365 1.1130 0.026 Uiso 1 1 calc R U . . .
C5 C 0.2539(2) 0.54295(14) 0.95931(12) 0.0196(3) Uani 1 1 d . . . . .
H5 H 0.2534 0.6243 0.9388 0.023 Uiso 1 1 calc R U . . .
C6 C 0.2539(2) 0.10663(14) 0.99479(12) 0.0216(3) Uani 1 1 d . . . . .
C7 C 0.2404(2) -0.01101(14) 1.05527(12) 0.0194(3) Uani 1 1 d . . . . .
C8 C 0.2599(3) -0.10888(15) 1.00727(13) 0.0295(4) Uani 1 1 d . . . . .
H8 H 0.2739 -0.0996 0.9347 0.035 Uiso 1 1 calc R U . . .
C9 C 0.2365(3) -0.22200(16) 1.16214(14) 0.0356(5) Uani 1 1 d . . . . .
H9 H 0.2371 -0.2969 1.2032 0.043 Uiso 1 1 calc R U . . .
C10 C 0.2121(2) -0.12405(15) 1.21015(12) 0.0247(4) Uani 1 1 d . . . . .
H10 H 0.1933 -0.1328 1.2823 0.030 Uiso 1 1 calc R U . . .
C11 C 0.2477(2) 0.37713(13) 0.60575(11) 0.0167(3) Uani 1 1 d . . . . .
H11 H 0.3743 0.3751 0.6102 0.020 Uiso 1 1 calc R U . . .
C12 C 0.1917(2) 0.30583(13) 0.54540(11) 0.0151(3) Uani 1 1 d . . . . .
C13 C 0.0056(2) 0.30868(13) 0.54069(11) 0.0168(3) Uani 1 1 d . . . . .
H13 H -0.0362 0.2602 0.5009 0.020 Uiso 1 1 calc R U . . .
C14 C -0.1173(2) 0.38280(14) 0.59463(12) 0.0183(3) Uani 1 1 d . . . . .
H14 H -0.2445 0.3861 0.5922 0.022 Uiso 1 1 calc R U . . .
C15 C -0.0524(2) 0.45206(14) 0.65209(12) 0.0178(3) Uani 1 1 d . . . . .
H15 H -0.1372 0.5035 0.6886 0.021 Uiso 1 1 calc R U . . .
C16 C 0.5004(2) 0.19627(13) 0.50151(11) 0.0170(3) Uani 1 1 d . . . . .
C17 C 0.5926(2) 0.11642(13) 0.42878(11) 0.0160(3) Uani 1 1 d . . . . .
C18 C 0.7787(2) 0.05843(14) 0.44468(12) 0.0191(3) Uani 1 1 d . . . . .
H18 H 0.8457 0.0713 0.5007 0.023 Uiso 1 1 calc R U . . .
C19 C 0.7644(2) -0.02827(14) 0.30565(12) 0.0212(3) Uani 1 1 d . . . . .
H19 H 0.8213 -0.0786 0.2591 0.025 Uiso 1 1 calc R U . . .
C20 C 0.5783(2) 0.02885(15) 0.29044(13) 0.0236(3) Uani 1 1 d . . . . .
H20 H 0.5115 0.0161 0.2342 0.028 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
Zn1 N5 2.0436(13) . ?
Zn1 N1 2.0497(12) . ?
Zn1 Cl2 2.2206(5) . ?
Zn1 Cl1 2.2309(4) . ?
O1 C6 1.2229(19) . ?
O2 C16 1.2219(19) . ?
N1 C5 1.340(2) . ?
N1 C1 1.3458(19) . ?
N2 C6 1.355(2) . ?
N2 C2 1.407(2) . ?
N2 H2N 0.80(2) . ?
N3 C9 1.335(2) . ?
N3 C8 1.337(2) . ?
N4 C10 1.335(2) . ?
N4 C7 1.338(2) . ?
N5 C15 1.342(2) . ?
N5 C11 1.3468(19) . ?
N6 C16 1.360(2) . ?
N6 C12 1.4029(19) . ?
N6 H6N 0.852(19) . ?
N7 C19 1.331(2) . ?
N7 C18 1.340(2) . ?
N8 C20 1.335(2) . ?
N8 C17 1.336(2) . ?
C1 C2 1.392(2) . ?
C1 H1 0.9500 . ?
C2 C3 1.394(2) . ?
C3 C4 1.377(2) . ?
C3 H3 0.9500 . ?
C4 C5 1.386(2) . ?
C4 H4 0.9500 . ?
C5 H5 0.9500 . ?
C6 C7 1.502(2) . ?
C7 C8 1.386(2) . ?
C8 H8 0.9500 . ?
C9 C10 1.383(2) . ?
C9 H9 0.9500 . ?
C10 H10 0.9500 . ?
C11 C12 1.393(2) . ?
C11 H11 0.9500 . ?
C12 C13 1.396(2) . ?
C13 C14 1.383(2) . ?
C13 H13 0.9500 . ?
C14 C15 1.382(2) . ?
C14 H14 0.9500 . ?
C15 H15 0.9500 . ?
C16 C17 1.501(2) . ?
C17 C18 1.385(2) . ?
C18 H18 0.9500 . ?
C19 C20 1.382(2) . ?
C19 H19 0.9500 . ?
C20 H20 0.9500 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
N5 Zn1 N1 103.66(5) . . ?
N5 Zn1 Cl2 106.99(4) . . ?
N1 Zn1 Cl2 109.18(4) . . ?
N5 Zn1 Cl1 111.97(4) . . ?
N1 Zn1 Cl1 106.93(4) . . ?
Cl2 Zn1 Cl1 117.259(17) . . ?
C5 N1 C1 119.37(13) . . ?
C5 N1 Zn1 117.94(10) . . ?
C1 N1 Zn1 122.64(10) . . ?
C6 N2 C2 126.87(14) . . ?
C6 N2 H2N 115.1(14) . . ?
C2 N2 H2N 118.0(14) . . ?
C9 N3 C8 115.86(16) . . ?
C10 N4 C7 116.51(14) . . ?
C15 N5 C11 119.53(13) . . ?
C15 N5 Zn1 119.91(10) . . ?
C11 N5 Zn1 120.34(10) . . ?
C16 N6 C12 126.31(13) . . ?
C16 N6 H6N 116.5(13) . . ?
C12 N6 H6N 117.1(13) . . ?
C19 N7 C18 115.73(14) . . ?
C20 N8 C17 115.59(14) . . ?
N1 C1 C2 121.72(14) . . ?
N1 C1 H1 119.1 . . ?
C2 C1 H1 119.1 . . ?
C1 C2 C3 118.67(14) . . ?
C1 C2 N2 123.06(14) . . ?
C3 C2 N2 118.27(14) . . ?
C4 C3 C2 118.90(14) . . ?
C4 C3 H3 120.5 . . ?
C2 C3 H3 120.5 . . ?
C3 C4 C5 119.59(15) . . ?
C3 C4 H4 120.2 . . ?
C5 C4 H4 120.2 . . ?
N1 C5 C4 121.67(14) . . ?
N1 C5 H5 119.2 . . ?
C4 C5 H5 119.2 . . ?
O1 C6 N2 125.09(15) . . ?
O1 C6 C7 121.51(14) . . ?
N2 C6 C7 113.37(13) . . ?
N4 C7 C8 122.17(15) . . ?
N4 C7 C6 117.28(14) . . ?
C8 C7 C6 120.52(14) . . ?
N3 C8 C7 121.46(16) . . ?
N3 C8 H8 119.3 . . ?
C7 C8 H8 119.3 . . ?
N3 C9 C10 123.03(16) . . ?
N3 C9 H9 118.5 . . ?
C10 C9 H9 118.5 . . ?
N4 C10 C9 120.93(15) . . ?
N4 C10 H10 119.5 . . ?
C9 C10 H10 119.5 . . ?
N5 C11 C12 121.51(14) . . ?
N5 C11 H11 119.2 . . ?
C12 C11 H11 119.2 . . ?
C11 C12 C13 118.57(14) . . ?
C11 C12 N6 122.73(14) . . ?
C13 C12 N6 118.67(13) . . ?
C14 C13 C12 119.29(14) . . ?
C14 C13 H13 120.4 . . ?
C12 C13 H13 120.4 . . ?
C15 C14 C13 119.03(14) . . ?
C15 C14 H14 120.5 . . ?
C13 C14 H14 120.5 . . ?
N5 C15 C14 122.06(14) . . ?
N5 C15 H15 119.0 . . ?
C14 C15 H15 119.0 . . ?
O2 C16 N6 124.91(14) . . ?
O2 C16 C17 121.35(14) . . ?
N6 C16 C17 113.70(13) . . ?
N8 C17 C18 122.41(14) . . ?
N8 C17 C16 118.17(13) . . ?
C18 C17 C16 119.40(13) . . ?
N7 C18 C17 121.72(14) . . ?
N7 C18 H18 119.1 . . ?
C17 C18 H18 119.1 . . ?
N7 C19 C20 122.47(15) . . ?
N7 C19 H19 118.8 . . ?
C20 C19 H19 118.8 . . ?
N8 C20 C19 122.06(15) . . ?
N8 C20 H20 119.0 . . ?
C19 C20 H20 119.0 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C5 N1 C1 C2 0.0(2) . . . . ?
Zn1 N1 C1 C2 177.31(11) . . . . ?
N1 C1 C2 C3 -2.3(2) . . . . ?
N1 C1 C2 N2 177.38(15) . . . . ?
C6 N2 C2 C1 20.8(3) . . . . ?
C6 N2 C2 C3 -159.49(16) . . . . ?
C1 C2 C3 C4 2.6(2) . . . . ?
N2 C2 C3 C4 -177.08(15) . . . . ?
C2 C3 C4 C5 -0.8(2) . . . . ?
C1 N1 C5 C4 2.0(2) . . . . ?
Zn1 N1 C5 C4 -175.44(12) . . . . ?
C3 C4 C5 N1 -1.6(2) . . . . ?
C2 N2 C6 O1 -0.8(3) . . . . ?
C2 N2 C6 C7 177.49(15) . . . . ?
C10 N4 C7 C8 1.3(2) . . . . ?
C10 N4 C7 C6 -176.74(15) . . . . ?
O1 C6 C7 N4 176.49(16) . . . . ?
N2 C6 C7 N4 -1.8(2) . . . . ?
O1 C6 C7 C8 -1.6(3) . . . . ?
N2 C6 C7 C8 -179.95(16) . . . . ?
C9 N3 C8 C7 0.9(3) . . . . ?
N4 C7 C8 N3 -2.1(3) . . . . ?
C6 C7 C8 N3 175.96(18) . . . . ?
C8 N3 C9 C10 0.9(3) . . . . ?
C7 N4 C10 C9 0.4(3) . . . . ?
N3 C9 C10 N4 -1.6(3) . . . . ?
C15 N5 C11 C12 0.1(2) . . . . ?
Zn1 N5 C11 C12 -174.44(11) . . . . ?
N5 C11 C12 C13 -0.8(2) . . . . ?
N5 C11 C12 N6 177.69(13) . . . . ?
C16 N6 C12 C11 19.2(2) . . . . ?
C16 N6 C12 C13 -162.36(14) . . . . ?
C11 C12 C13 C14 0.8(2) . . . . ?
N6 C12 C13 C14 -177.74(13) . . . . ?
C12 C13 C14 C15 -0.1(2) . . . . ?
C11 N5 C15 C14 0.7(2) . . . . ?
Zn1 N5 C15 C14 175.18(11) . . . . ?
C13 C14 C15 N5 -0.6(2) . . . . ?
C12 N6 C16 O2 0.2(3) . . . . ?
C12 N6 C16 C17 178.25(13) . . . . ?
C20 N8 C17 C18 -1.5(2) . . . . ?
C20 N8 C17 C16 -179.56(14) . . . . ?
O2 C16 C17 N8 -174.43(15) . . . . ?
N6 C16 C17 N8 7.5(2) . . . . ?
O2 C16 C17 C18 7.5(2) . . . . ?
N6 C16 C17 C18 -170.64(14) . . . . ?
C19 N7 C18 C17 0.6(2) . . . . ?
N8 C17 C18 N7 0.8(2) . . . . ?
C16 C17 C18 N7 178.83(14) . . . . ?
C18 N7 C19 C20 -1.2(2) . . . . ?
C17 N8 C20 C19 0.9(2) . . . . ?
N7 C19 C20 N8 0.4(3) . . . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
N2 H2N Cl1 0.80(2) 2.87(2) 3.5377(14) 141.9(17) 2_567
N2 H2N N4 0.80(2) 2.221(19) 2.6541(19) 114.2(16) .
N6 H6N Cl1 0.852(19) 2.75(2) 3.5262(14) 151.4(16) 2_566
N6 H6N N8 0.852(19) 2.258(19) 2.6831(19) 110.9(15) .
C1 H1 O1 0.95 2.29 2.874(2) 119.4 .
C3 H3 Cl1 0.95 2.92 3.4990(16) 120.5 2_567
C4 H4 Cl2 0.95 2.99 3.6137(17) 124.9 2_667
C5 H5 N3 0.95 2.69 3.356(2) 127.8 1_565
C10 H10 O2 0.95 2.45 3.156(2) 130.9 2_657
C11 H11 Cl2 0.95 2.94 3.5219(16) 120.6 .
C11 H11 O2 0.95 2.24 2.8390(19) 120.1 .
C13 H13 Cl1 0.95 2.94 3.5909(16) 127.0 2_566
C14 H14 Cl2 0.95 2.94 3.5160(16) 120.0 1_455
C14 H14 O2 0.95 2.65 3.3420(19) 130.5 1_455
C15 H15 Cl2 0.95 2.71 3.4137(16) 131.3 1_455
C18 H18 N7 0.95 2.52 3.377(2) 150.1 2_756
C19 H19 O1 0.95 2.44 3.170(2) 133.0 2_656
C20 H20 N4 0.95 2.61 3.472(2) 150.6 1_554

_refine_diff_density_max         0.376
_refine_diff_density_min         -0.255
_refine_diff_density_rms         0.057

