# Electronic Supplementary Material (ESI) for Dalton Transactions.
# This journal is © The Royal Society of Chemistry 2019

####################################################################### 
# 
# 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_shelx
_database_code_depnum_ccdc_archive 'CCDC 1914359'
loop_
_audit_author_name
_audit_author_address
'Dr. Tapan Kumar Mondal'
;Jadavpur University
India
;
_audit_update_record             
;
2019-11-02 deposited with the CCDC.	2019-11-18 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2016/6
_shelx_SHELXL_version_number     2016/6
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C22 H16 Cl2 Hg N4 O'
_chemical_formula_weight         623.88

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'
Hg Hg -2.3894 9.2266 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
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'

_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                   7.5222(6)
_cell_length_b                   9.2463(7)
_cell_length_c                   16.0762(12)
_cell_angle_alpha                75.104(2)
_cell_angle_beta                 89.593(2)
_cell_angle_gamma                79.724(2)
_cell_volume                     1062.35(14)
_cell_formula_units_Z            2
_cell_measurement_temperature    273(2)
_cell_measurement_reflns_used    7245
_cell_measurement_theta_min      2.25
_cell_measurement_theta_max      22.00

_exptl_crystal_description       nidle
_exptl_crystal_colour            red
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.950
_exptl_crystal_F_000             596
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.14
_exptl_crystal_size_mid          0.08
_exptl_crystal_size_min          0.07
_exptl_absorpt_coefficient_mu    7.517
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.4246
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_process_details   'SADABS 2016/2 (Bruker, 2016)'
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      273(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'fine-focus sealed tube'
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'Omega/Phi scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            36664
_diffrn_reflns_av_unetI/netI     0.0202
_diffrn_reflns_av_R_equivalents  0.0363
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_theta_min         2.318
_diffrn_reflns_theta_max         27.110
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.995
_diffrn_measured_fraction_theta_full 0.995
_diffrn_reflns_Laue_measured_fraction_max 0.995
_diffrn_reflns_Laue_measured_fraction_full 0.995
_diffrn_reflns_point_group_measured_fraction_max 0.995
_diffrn_reflns_point_group_measured_fraction_full 0.995
_reflns_number_total             4673
_reflns_number_gt                4399
_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       'Apex3 v2017.3-0 (Bruker, 2016)'
_computing_cell_refinement       'SAINT V8.38A (Bruker, 2016)'
_computing_data_reduction        'SAINT V8.38A (Bruker, 2016)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2016/6 (Sheldrick, 2016)'
_computing_molecular_graphics    'Ortep-3 for Windows (Farrugia, 2012)'
_computing_publication_material  'WinGX v2018.3'
_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)+(0.0194P)²+0.7885P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         4673
_refine_ls_number_parameters     275
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0200
_refine_ls_R_factor_gt           0.0179
_refine_ls_wR_factor_ref         0.0440
_refine_ls_wR_factor_gt          0.0428
_refine_ls_goodness_of_fit_ref   1.012
_refine_ls_restrained_S_all      1.012
_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 0.72611(2) 0.76161(2) 0.34679(2) 0.04160(4) Uani 1 1 d . . . . .
Cl1 Cl 0.41023(9) 0.89912(8) 0.32971(5) 0.04838(16) Uani 1 1 d . . . . .
Cl2 Cl 0.94018(11) 0.91274(10) 0.28816(7) 0.0663(2) Uani 1 1 d . . . . .
O1 O 0.6701(3) 0.7042(2) 0.19257(12) 0.0553(5) Uani 1 1 d . . . . .
N1 N 0.7748(3) 0.6119(2) 0.48535(13) 0.0340(4) Uani 1 1 d . . . . .
N2 N 0.7596(3) 0.3954(3) 0.58094(14) 0.0346(4) Uani 1 1 d . . . . .
N3 N 0.6869(3) 0.5083(2) 0.34816(13) 0.0312(4) Uani 1 1 d . . . . .
N4 N 0.6957(5) 0.8543(4) -0.03333(19) 0.0727(9) Uani 1 1 d . . . . .
C1 C 0.8151(3) 0.6273(3) 0.56619(16) 0.0337(5) Uani 1 1 d . . . . .
C2 C 0.8587(4) 0.7508(3) 0.5920(2) 0.0448(6) Uani 1 1 d . . . . .
H2 H 0.865313 0.842425 0.552178 0.054 Uiso 1 1 calc R U . . .
C3 C 0.8909(4) 0.7309(4) 0.6782(2) 0.0507(7) Uani 1 1 d . . . . .
H3 H 0.920030 0.811054 0.697184 0.061 Uiso 1 1 calc R U . . .
C4 C 0.8815(4) 0.5935(4) 0.7387(2) 0.0526(7) Uani 1 1 d . . . . .
H4 H 0.905697 0.584650 0.796602 0.063 Uiso 1 1 calc R U . . .
C5 C 0.8374(4) 0.4715(3) 0.71492(18) 0.0452(6) Uani 1 1 d . . . . .
H5 H 0.829227 0.380835 0.755221 0.054 Uiso 1 1 calc R U . . .
C6 C 0.8056(3) 0.4910(3) 0.62709(16) 0.0340(5) Uani 1 1 d . . . . .
C7 C 0.7432(3) 0.4726(3) 0.49712(15) 0.0303(5) Uani 1 1 d . . . . .
C8 C 0.6955(3) 0.4122(3) 0.42532(15) 0.0303(5) Uani 1 1 d . . . . .
C9 C 0.6628(4) 0.2627(3) 0.43955(17) 0.0379(5) Uani 1 1 d . . . . .
H9 H 0.670859 0.198253 0.494853 0.046 Uiso 1 1 calc R U . . .
C10 C 0.6189(4) 0.2149(3) 0.37029(18) 0.0414(6) Uani 1 1 d . . . . .
H10 H 0.596287 0.116741 0.378191 0.050 Uiso 1 1 calc R U . . .
C11 C 0.6076(3) 0.3128(3) 0.28712(17) 0.0374(5) Uani 1 1 d . . . . .
C12 C 0.5601(4) 0.2701(4) 0.2128(2) 0.0512(7) Uani 1 1 d . . . . .
H12 H 0.537975 0.172547 0.217697 0.061 Uiso 1 1 calc R U . . .
C13 C 0.5470(5) 0.3713(4) 0.1351(2) 0.0596(8) Uani 1 1 d . . . . .
H13 H 0.513818 0.342670 0.086846 0.072 Uiso 1 1 calc R U . . .
C14 C 0.5822(5) 0.5192(4) 0.12485(19) 0.0557(8) Uani 1 1 d . . . . .
H14 H 0.572336 0.586478 0.070338 0.067 Uiso 1 1 calc R U . . .
C15 C 0.6309(4) 0.5647(3) 0.19496(17) 0.0429(6) Uani 1 1 d . . . . .
C16 C 0.6427(3) 0.4615(3) 0.27835(16) 0.0341(5) Uani 1 1 d . . . . .
C17 C 0.6240(6) 0.8251(4) 0.1148(2) 0.0641(9) Uani 1 1 d . . . . .
H17A H 0.614470 0.922235 0.128604 0.077 Uiso 1 1 calc R U . . .
H17B H 0.506695 0.820115 0.092110 0.077 Uiso 1 1 calc R U . . .
C18 C 0.7608(5) 0.8165(4) 0.0467(2) 0.0571(8) Uani 1 1 d . . . . .
C19 C 0.9395(7) 0.7782(9) 0.0661(3) 0.133(3) Uani 1 1 d . . . . .
H19 H 0.982414 0.753820 0.123066 0.160 Uiso 1 1 calc R U . . .
C20 C 1.0587(8) 0.7755(11) 0.0004(4) 0.161(4) Uani 1 1 d . . . . .
H20 H 1.182405 0.745785 0.012980 0.194 Uiso 1 1 calc R U . . .
C21 C 0.9946(7) 0.8162(7) -0.0818(3) 0.0964(16) Uani 1 1 d . . . . .
H21 H 1.072034 0.817688 -0.127284 0.116 Uiso 1 1 calc R U . . .
C22 C 0.8163(6) 0.8541(6) -0.0956(3) 0.0841(13) Uani 1 1 d . . . . .
H22 H 0.771675 0.882513 -0.152393 0.101 Uiso 1 1 calc R U . . .
H2N H 0.739(4) 0.317(4) 0.598(2) 0.045(9) Uiso 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
Hg1 N1 2.293(2) . ?
Hg1 Cl2 2.3533(8) . ?
Hg1 N3 2.407(2) . ?
Hg1 Cl1 2.4678(7) . ?
O1 C15 1.364(4) . ?
O1 C17 1.443(4) . ?
N1 C7 1.317(3) . ?
N1 C1 1.385(3) . ?
N2 C7 1.348(3) . ?
N2 C6 1.379(3) . ?
N2 H2N 0.75(3) . ?
N3 C8 1.322(3) . ?
N3 C16 1.365(3) . ?
N4 C18 1.317(4) . ?
N4 C22 1.347(5) . ?
C1 C6 1.396(4) . ?
C1 C2 1.401(4) . ?
C2 C3 1.368(4) . ?
C2 H2 0.9300 . ?
C3 C4 1.401(5) . ?
C3 H3 0.9300 . ?
C4 C5 1.373(4) . ?
C4 H4 0.9300 . ?
C5 C6 1.393(4) . ?
C5 H5 0.9300 . ?
C7 C8 1.478(3) . ?
C8 C9 1.407(3) . ?
C9 C10 1.362(4) . ?
C9 H9 0.9300 . ?
C10 C11 1.402(4) . ?
C10 H10 0.9300 . ?
C11 C12 1.418(4) . ?
C11 C16 1.417(4) . ?
C12 C13 1.347(5) . ?
C12 H12 0.9300 . ?
C13 C14 1.407(5) . ?
C13 H13 0.9300 . ?
C14 C15 1.374(4) . ?
C14 H14 0.9300 . ?
C15 C16 1.425(4) . ?
C17 C18 1.505(5) . ?
C17 H17A 0.9700 . ?
C17 H17B 0.9700 . ?
C18 C19 1.345(6) . ?
C19 C20 1.383(8) . ?
C19 H19 0.9300 . ?
C20 C21 1.346(7) . ?
C20 H20 0.9300 . ?
C21 C22 1.329(6) . ?
C21 H21 0.9300 . ?
C22 H22 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
N1 Hg1 Cl2 118.72(6) . . ?
N1 Hg1 N3 71.51(7) . . ?
Cl2 Hg1 N3 134.03(5) . . ?
N1 Hg1 Cl1 108.38(6) . . ?
Cl2 Hg1 Cl1 114.54(3) . . ?
N3 Hg1 Cl1 101.51(5) . . ?
C15 O1 C17 118.5(2) . . ?
C7 N1 C1 106.3(2) . . ?
C7 N1 Hg1 115.17(16) . . ?
C1 N1 Hg1 138.29(16) . . ?
C7 N2 C6 107.5(2) . . ?
C7 N2 H2N 124(3) . . ?
C6 N2 H2N 128(3) . . ?
C8 N3 C16 118.7(2) . . ?
C8 N3 Hg1 115.24(15) . . ?
C16 N3 Hg1 125.85(16) . . ?
C18 N4 C22 117.0(4) . . ?
N1 C1 C6 108.6(2) . . ?
N1 C1 C2 131.0(2) . . ?
C6 C1 C2 120.4(2) . . ?
C3 C2 C1 117.1(3) . . ?
C3 C2 H2 121.4 . . ?
C1 C2 H2 121.4 . . ?
C2 C3 C4 121.9(3) . . ?
C2 C3 H3 119.0 . . ?
C4 C3 H3 119.0 . . ?
C5 C4 C3 121.9(3) . . ?
C5 C4 H4 119.1 . . ?
C3 C4 H4 119.1 . . ?
C4 C5 C6 116.3(3) . . ?
C4 C5 H5 121.8 . . ?
C6 C5 H5 121.8 . . ?
N2 C6 C5 132.1(3) . . ?
N2 C6 C1 105.6(2) . . ?
C5 C6 C1 122.3(2) . . ?
N1 C7 N2 112.0(2) . . ?
N1 C7 C8 122.6(2) . . ?
N2 C7 C8 125.4(2) . . ?
N3 C8 C9 123.4(2) . . ?
N3 C8 C7 115.0(2) . . ?
C9 C8 C7 121.6(2) . . ?
C10 C9 C8 118.3(2) . . ?
C10 C9 H9 120.8 . . ?
C8 C9 H9 120.8 . . ?
C9 C10 C11 120.4(2) . . ?
C9 C10 H10 119.8 . . ?
C11 C10 H10 119.8 . . ?
C10 C11 C12 122.9(3) . . ?
C10 C11 C16 117.7(2) . . ?
C12 C11 C16 119.3(3) . . ?
C13 C12 C11 119.8(3) . . ?
C13 C12 H12 120.1 . . ?
C11 C12 H12 120.1 . . ?
C12 C13 C14 121.7(3) . . ?
C12 C13 H13 119.1 . . ?
C14 C13 H13 119.1 . . ?
C15 C14 C13 120.4(3) . . ?
C15 C14 H14 119.8 . . ?
C13 C14 H14 119.8 . . ?
O1 C15 C14 125.4(3) . . ?
O1 C15 C16 115.2(2) . . ?
C14 C15 C16 119.3(3) . . ?
N3 C16 C11 121.4(2) . . ?
N3 C16 C15 119.2(2) . . ?
C11 C16 C15 119.3(2) . . ?
O1 C17 C18 112.7(3) . . ?
O1 C17 H17A 109.1 . . ?
C18 C17 H17A 109.1 . . ?
O1 C17 H17B 109.1 . . ?
C18 C17 H17B 109.1 . . ?
H17A C17 H17B 107.8 . . ?
N4 C18 C19 121.9(4) . . ?
N4 C18 C17 116.0(3) . . ?
C19 C18 C17 122.0(3) . . ?
C18 C19 C20 119.2(5) . . ?
C18 C19 H19 120.4 . . ?
C20 C19 H19 120.4 . . ?
C21 C20 C19 119.6(5) . . ?
C21 C20 H20 120.2 . . ?
C19 C20 H20 120.2 . . ?
C22 C21 C20 117.4(5) . . ?
C22 C21 H21 121.3 . . ?
C20 C21 H21 121.3 . . ?
C21 C22 N4 124.8(4) . . ?
C21 C22 H22 117.6 . . ?
N4 C22 H22 117.6 . . ?

_refine_diff_density_max         0.503
_refine_diff_density_min         -0.829
_refine_diff_density_rms         0.065

