# Electronic Supplementary Material (ESI) for Inorganic Chemistry Frontiers.
# This journal is © the Partner Organisations 2014

 
data_Complex3 
 
_audit_creation_method            SHELXL-97 
_chemical_name_systematic 
; 
 ? 
; 
_chemical_name_common             ? 
_chemical_melting_point           ? 
_chemical_formula_moiety          ? 
_chemical_formula_sum 
 'C36 H30 Cl2 Hg N6 O4' 
_chemical_formula_weight          882.15 
 
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' 
 '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' 
 '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' 
 
_symmetry_cell_setting            'Monoclinic' 
_symmetry_space_group_name_H-M    'C2/c' 
 
loop_ 
 _symmetry_equiv_pos_as_xyz 
 'x, y, z' 
 '-x, y, -z+1/2' 
 'x+1/2, y+1/2, z' 
 '-x+1/2, y+1/2, -z+1/2' 
 '-x, -y, -z' 
 'x, -y, z-1/2' 
 '-x+1/2, -y+1/2, -z' 
 'x+1/2, -y+1/2, z-1/2' 
 
_cell_length_a                    14.7824(3) 
_cell_length_b                    12.0395(3) 
_cell_length_c                    19.7994(5) 
_cell_angle_alpha                 90.00 
_cell_angle_beta                  104.923(2) 
_cell_angle_gamma                 90.00 
_cell_volume                      3404.91(14) 
_cell_formula_units_Z             4 
_cell_measurement_temperature     296(2) 
_cell_measurement_reflns_used     5824 
_cell_measurement_theta_min       2.21 
_cell_measurement_theta_max       22.75 
 
_exptl_crystal_description        block 
_exptl_crystal_colour             colourless 
_exptl_crystal_size_max           0.30 
_exptl_crystal_size_mid           0.23 
_exptl_crystal_size_min           0.17 
_exptl_crystal_density_meas       ? 
_exptl_crystal_density_diffrn     1.721 
_exptl_crystal_density_method     'not measured' 
_exptl_crystal_F_000              1736 
_exptl_absorpt_coefficient_mu     4.727 
_exptl_absorpt_correction_type    'multi-scan' 
_exptl_absorpt_correction_T_min   0.282 
_exptl_absorpt_correction_T_max   0.448 
_exptl_absorpt_process_details    'Face indexing' 
 
_exptl_special_details 
; 
 ? 
; 
 
_diffrn_ambient_temperature       296(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   ? 
_diffrn_measurement_method        ? 
_diffrn_detector_area_resol_mean  ? 
_diffrn_standards_number          ? 
_diffrn_standards_interval_count  ? 
_diffrn_standards_interval_time   ? 
_diffrn_standards_decay_%         ? 
_diffrn_reflns_number             25357 
_diffrn_reflns_av_R_equivalents   0.0474 
_diffrn_reflns_av_sigmaI/netI     0.0324 
_diffrn_reflns_limit_h_min        -17 
_diffrn_reflns_limit_h_max        17 
_diffrn_reflns_limit_k_min        -13 
_diffrn_reflns_limit_k_max        14 
_diffrn_reflns_limit_l_min        -23 
_diffrn_reflns_limit_l_max        23 
_diffrn_reflns_theta_min          2.13 
_diffrn_reflns_theta_max          25.24 
_reflns_number_total              3066 
_reflns_number_gt                 2402 
_reflns_threshold_expression      >2sigma(I) 
 
_computing_data_collection        ? 
_computing_cell_refinement        ? 
_computing_data_reduction         ? 
_computing_structure_solution     'SHELXS-97 (Sheldrick, 1990)' 
_computing_structure_refinement   'SHELXL-97 (Sheldrick, 1997)' 
_computing_molecular_graphics     ? 
_computing_publication_material   ? 
 
_refine_special_details 
; 
 Refinement of F² against ALL reflections.  The weighted R-factor wR and 
 goodness of fit S are based on F², conventional R-factors R are based 
 on F, with F set to zero for negative F². The threshold expression of 
 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is 
 not relevant to the choice of reflections for refinement.  R-factors based 
 on F² are statistically about twice as large as those based on F, and R- 
 factors based on ALL data will be even larger. 
; 
 
_refine_ls_structure_factor_coef  Fsqd  
_refine_ls_matrix_type            full 
_refine_ls_weighting_scheme       calc  
_refine_ls_weighting_details 
 'calc w=1/[σ²(Fo²)+(0.0000P)²+100.1221P] 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          3066 
_refine_ls_number_parameters      222 
_refine_ls_number_restraints      0 
_refine_ls_R_factor_all           0.0935 
_refine_ls_R_factor_gt            0.0720 
_refine_ls_wR_factor_ref          0.1432 
_refine_ls_wR_factor_gt           0.1346 
_refine_ls_goodness_of_fit_ref    1.104 
_refine_ls_restrained_S_all       1.104 
_refine_ls_shift/su_max           0.000 
_refine_ls_shift/su_mean          0.000 
 
loop_ 
 _atom_site_label 
 _atom_site_type_symbol 
 _atom_site_fract_x 
 _atom_site_fract_y 
 _atom_site_fract_z 
 _atom_site_U_iso_or_equiv 
 _atom_site_adp_type 
 _atom_site_occupancy 
 _atom_site_symmetry_multiplicity 
 _atom_site_calc_flag 
 _atom_site_refinement_flags 
 _atom_site_disorder_assembly 
 _atom_site_disorder_group 
C1 C 0.5717(6) 0.0356(8) 0.1264(5) 0.040(2) Uani 1 1 d . . . 
H1 H 0.5513 -0.0223 0.0951 0.048 Uiso 1 1 calc R . . 
C2 C 0.5992(7) 0.1368(9) 0.2174(5) 0.049(3) Uani 1 1 d . . . 
H2 H 0.6012 0.1627 0.2620 0.058 Uiso 1 1 calc R . . 
C3 C 0.6381(7) 0.1888(9) 0.1713(5) 0.052(3) Uani 1 1 d . . . 
H3 H 0.6707 0.2557 0.1779 0.062 Uiso 1 1 calc R . . 
C4 C 0.6512(8) 0.1427(8) 0.0493(5) 0.053(3) Uani 1 1 d . . . 
H4A H 0.6203 0.0898 0.0139 0.064 Uiso 1 1 calc R . . 
H4B H 0.7181 0.1293 0.0595 0.064 Uiso 1 1 calc R . . 
C5 C 0.6310(7) 0.2581(8) 0.0208(5) 0.048(3) Uani 1 1 d . . . 
H5 H 0.6660 0.2698 -0.0139 0.058 Uiso 1 1 calc R . . 
H20B H 0.6550 0.3102 0.0586 0.058 Uiso 1 1 calc R . . 
C6 C 0.5290(7) 0.2872(9) -0.0125(5) 0.050(3) Uani 1 1 d . . . 
H6 H 0.5268 0.3593 -0.0347 0.060 Uiso 1 1 calc R . . 
H21B H 0.5038 0.2332 -0.0488 0.060 Uiso 1 1 calc R . . 
C7 C 0.4044(7) 0.2034(7) 0.0347(5) 0.040(2) Uani 1 1 d . . . 
C8 C 0.3379(6) 0.2160(8) 0.0786(5) 0.040(2) Uani 1 1 d . . . 
C9 C 0.2729(7) 0.1343(9) 0.0786(5) 0.054(3) Uani 1 1 d . . . 
H9 H 0.2713 0.0707 0.0517 0.065 Uiso 1 1 calc R . . 
C10 C 0.2084(8) 0.1474(11) 0.1199(6) 0.065(3) Uani 1 1 d . . . 
H10 H 0.1657 0.0911 0.1209 0.078 Uiso 1 1 calc R . . 
C11 C 0.2080(8) 0.2401(10) 0.1575(6) 0.063(3) Uani 1 1 d . . . 
H29 H 0.1629 0.2484 0.1823 0.076 Uiso 1 1 calc R . . 
C12 C 0.2737(7) 0.3242(9) 0.1601(5) 0.048(2) Uani 1 1 d . . . 
C13 C 0.3397(6) 0.3127(8) 0.1197(5) 0.039(2) Uani 1 1 d . . . 
C14 C 0.2798(8) 0.4202(10) 0.2023(6) 0.064(3) Uani 1 1 d . . . 
H26 H 0.2384 0.4290 0.2302 0.077 Uiso 1 1 calc R . . 
C15 C 0.3451(9) 0.4995(11) 0.2026(6) 0.071(3) Uani 1 1 d . . . 
H15 H 0.3469 0.5626 0.2300 0.085 Uiso 1 1 calc R . . 
C16 C 0.4092(8) 0.4881(9) 0.1629(6) 0.057(3) Uani 1 1 d . . . 
H16 H 0.4539 0.5430 0.1643 0.069 Uiso 1 1 calc R . . 
C17 C 0.4070(7) 0.3958(8) 0.1211(5) 0.042(2) Uani 1 1 d . . . 
C18 C 0.4754(7) 0.3844(7) 0.0792(5) 0.043(2) Uani 1 1 d . . . 
Cl1 Cl 0.6262(4) -0.1846(5) 0.3349(3) 0.170(3) Uani 1 1 d . . . 
Hg1 Hg 0.5000 -0.08939(6) 0.2500 0.0759(3) Uani 1 2 d S . . 
N1 N 0.5569(6) 0.0411(6) 0.1892(4) 0.0428(19) Uani 1 1 d . . . 
N2 N 0.6197(5) 0.1238(6) 0.1133(4) 0.0386(18) Uani 1 1 d . . . 
N3 N 0.4675(5) 0.2904(6) 0.0361(4) 0.0411(19) Uani 1 1 d . . . 
O1 O 0.4058(5) 0.1226(6) -0.0019(4) 0.0567(19) Uani 1 1 d . . . 
O2 O 0.5362(5) 0.4527(6) 0.0800(4) 0.062(2) Uani 1 1 d . . . 
 
 
_geom_special_details 
; 
 All esds (except the esd in the dihedral angle between two l.s. planes) 
 are estimated using the full covariance matrix.  The cell esds are taken 
 into account individually in the estimation of esds in distances, angles 
 and torsion angles; correlations between esds in cell parameters are only 
 used when they are defined by crystal symmetry.  An approximate (isotropic) 
 treatment of cell esds is used for estimating esds involving l.s. planes. 
; 
 
loop_ 
 _geom_bond_atom_site_label_1 
 _geom_bond_atom_site_label_2 
 _geom_bond_distance 
 _geom_bond_site_symmetry_2 
 _geom_bond_publ_flag 
C1 N1 1.319(11) . ? 
C1 N2 1.338(11) . ? 
C1 H1 0.9300 . ? 
C2 C3 1.350(13) . ? 
C2 N1 1.361(12) . ? 
C2 H2 0.9300 . ? 
C3 N2 1.359(11) . ? 
C3 H3 0.9300 . ? 
C4 N2 1.477(11) . ? 
C4 C5 1.501(13) . ? 
C4 H4A 0.9700 . ? 
C4 H4B 0.9700 . ? 
C5 C6 1.522(14) . ? 
C5 H5 0.9700 . ? 
C5 H20B 0.9700 . ? 
C6 N3 1.485(11) . ? 
C6 H6 0.9700 . ? 
C6 H21B 0.9700 . ? 
C7 O1 1.217(11) . ? 
C7 N3 1.397(11) . ? 
C7 C8 1.478(12) . ? 
C8 C9 1.375(13) . ? 
C8 C13 1.417(13) . ? 
C9 C10 1.415(15) . ? 
C9 H9 0.9300 . ? 
C10 C11 1.342(16) . ? 
C10 H10 0.9300 . ? 
C11 C12 1.396(15) . ? 
C11 H29 0.9300 . ? 
C12 C14 1.415(15) . ? 
C12 C13 1.419(12) . ? 
C13 C17 1.406(13) . ? 
C14 C15 1.357(16) . ? 
C14 H26 0.9300 . ? 
C15 C16 1.385(15) . ? 
C15 H15 0.9300 . ? 
C16 C17 1.381(13) . ? 
C16 H16 0.9300 . ? 
C17 C18 1.470(12) . ? 
C18 O2 1.216(11) . ? 
C18 N3 1.403(11) . ? 
Cl1 Hg1 2.451(5) . ? 
Hg1 N1 2.268(7) . ? 
Hg1 N1 2.268(7) 2_655 ? 
Hg1 Cl1 2.451(5) 2_655 ? 
 
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 N2 111.5(8) . . ? 
N1 C1 H1 124.2 . . ? 
N2 C1 H1 124.2 . . ? 
C3 C2 N1 110.3(8) . . ? 
C3 C2 H2 124.9 . . ? 
N1 C2 H2 124.9 . . ? 
C2 C3 N2 106.0(8) . . ? 
C2 C3 H3 127.0 . . ? 
N2 C3 H3 127.0 . . ? 
N2 C4 C5 113.0(8) . . ? 
N2 C4 H4A 109.0 . . ? 
C5 C4 H4A 109.0 . . ? 
N2 C4 H4B 109.0 . . ? 
C5 C4 H4B 109.0 . . ? 
H4A C4 H4B 107.8 . . ? 
C4 C5 C6 117.0(9) . . ? 
C4 C5 H5 108.0 . . ? 
C6 C5 H5 108.0 . . ? 
C4 C5 H20B 108.0 . . ? 
C6 C5 H20B 108.0 . . ? 
H5 C5 H20B 107.3 . . ? 
N3 C6 C5 115.4(8) . . ? 
N3 C6 H6 108.4 . . ? 
C5 C6 H6 108.4 . . ? 
N3 C6 H21B 108.4 . . ? 
C5 C6 H21B 108.4 . . ? 
H6 C6 H21B 107.5 . . ? 
O1 C7 N3 119.9(8) . . ? 
O1 C7 C8 123.1(9) . . ? 
N3 C7 C8 116.9(8) . . ? 
C9 C8 C13 119.8(9) . . ? 
C9 C8 C7 119.9(9) . . ? 
C13 C8 C7 120.3(8) . . ? 
C8 C9 C10 119.7(11) . . ? 
C8 C9 H9 120.1 . . ? 
C10 C9 H9 120.1 . . ? 
C11 C10 C9 120.9(11) . . ? 
C11 C10 H10 119.6 . . ? 
C9 C10 H10 119.6 . . ? 
C10 C11 C12 121.4(10) . . ? 
C10 C11 H29 119.3 . . ? 
C12 C11 H29 119.3 . . ? 
C11 C12 C14 123.5(10) . . ? 
C11 C12 C13 118.8(10) . . ? 
C14 C12 C13 117.7(10) . . ? 
C17 C13 C8 120.4(8) . . ? 
C17 C13 C12 120.3(9) . . ? 
C8 C13 C12 119.3(9) . . ? 
C15 C14 C12 121.0(10) . . ? 
C15 C14 H26 119.5 . . ? 
C12 C14 H26 119.5 . . ? 
C14 C15 C16 121.2(11) . . ? 
C14 C15 H15 119.4 . . ? 
C16 C15 H15 119.4 . . ? 
C17 C16 C15 120.4(11) . . ? 
C17 C16 H16 119.8 . . ? 
C15 C16 H16 119.8 . . ? 
C16 C17 C13 119.5(9) . . ? 
C16 C17 C18 120.0(9) . . ? 
C13 C17 C18 120.5(8) . . ? 
O2 C18 N3 119.9(8) . . ? 
O2 C18 C17 123.0(9) . . ? 
N3 C18 C17 117.1(8) . . ? 
N1 Hg1 N1 92.3(4) . 2_655 ? 
N1 Hg1 Cl1 106.3(2) . 2_655 ? 
N1 Hg1 Cl1 111.5(2) 2_655 2_655 ? 
N1 Hg1 Cl1 111.5(2) . . ? 
N1 Hg1 Cl1 106.3(2) 2_655 . ? 
Cl1 Hg1 Cl1 124.2(3) 2_655 . ? 
C1 N1 C2 105.0(8) . . ? 
C1 N1 Hg1 129.8(6) . . ? 
C2 N1 Hg1 124.3(6) . . ? 
C1 N2 C3 107.1(7) . . ? 
C1 N2 C4 126.1(8) . . ? 
C3 N2 C4 126.7(8) . . ? 
C7 N3 C18 124.6(8) . . ? 
C7 N3 C6 118.9(8) . . ? 
C18 N3 C6 116.4(8) . . ? 
 
loop_ 
 _geom_torsion_atom_site_label_1 
 _geom_torsion_atom_site_label_2 
 _geom_torsion_atom_site_label_3 
 _geom_torsion_atom_site_label_4 
 _geom_torsion 
 _geom_torsion_site_symmetry_1 
 _geom_torsion_site_symmetry_2 
 _geom_torsion_site_symmetry_3 
 _geom_torsion_site_symmetry_4 
 _geom_torsion_publ_flag 
N1 C2 C3 N2 -0.2(12) . . . . ? 
N2 C4 C5 C6 -71.0(12) . . . . ? 
C4 C5 C6 N3 66.6(12) . . . . ? 
O1 C7 C8 C9 -0.7(15) . . . . ? 
N3 C7 C8 C9 178.9(9) . . . . ? 
O1 C7 C8 C13 -179.7(9) . . . . ? 
N3 C7 C8 C13 -0.1(13) . . . . ? 
C13 C8 C9 C10 -0.1(15) . . . . ? 
C7 C8 C9 C10 -179.0(9) . . . . ? 
C8 C9 C10 C11 1.9(17) . . . . ? 
C9 C10 C11 C12 -3.2(18) . . . . ? 
C10 C11 C12 C14 -176.0(11) . . . . ? 
C10 C11 C12 C13 2.6(16) . . . . ? 
C9 C8 C13 C17 178.8(9) . . . . ? 
C7 C8 C13 C17 -2.3(13) . . . . ? 
C9 C8 C13 C12 -0.4(14) . . . . ? 
C7 C8 C13 C12 178.5(8) . . . . ? 
C11 C12 C13 C17 -180.0(9) . . . . ? 
C14 C12 C13 C17 -1.3(14) . . . . ? 
C11 C12 C13 C8 -0.8(14) . . . . ? 
C14 C12 C13 C8 177.9(9) . . . . ? 
C11 C12 C14 C15 -179.8(11) . . . . ? 
C13 C12 C14 C15 1.5(16) . . . . ? 
C12 C14 C15 C16 -1.4(19) . . . . ? 
C14 C15 C16 C17 0.9(19) . . . . ? 
C15 C16 C17 C13 -0.6(16) . . . . ? 
C15 C16 C17 C18 -179.9(10) . . . . ? 
C8 C13 C17 C16 -178.4(9) . . . . ? 
C12 C13 C17 C16 0.9(14) . . . . ? 
C8 C13 C17 C18 0.9(14) . . . . ? 
C12 C13 C17 C18 -179.9(9) . . . . ? 
C16 C17 C18 O2 1.1(15) . . . . ? 
C13 C17 C18 O2 -178.2(9) . . . . ? 
C16 C17 C18 N3 -178.0(9) . . . . ? 
C13 C17 C18 N3 2.7(13) . . . . ? 
N2 C1 N1 C2 -1.1(11) . . . . ? 
N2 C1 N1 Hg1 -170.1(6) . . . . ? 
C3 C2 N1 C1 0.8(12) . . . . ? 
C3 C2 N1 Hg1 170.6(7) . . . . ? 
N1 Hg1 N1 C1 -152.9(10) 2_655 . . . ? 
Cl1 Hg1 N1 C1 -39.6(9) 2_655 . . . ? 
Cl1 Hg1 N1 C1 98.6(8) . . . . ? 
N1 Hg1 N1 C2 40.0(7) 2_655 . . . ? 
Cl1 Hg1 N1 C2 153.2(7) 2_655 . . . ? 
Cl1 Hg1 N1 C2 -68.6(8) . . . . ? 
N1 C1 N2 C3 1.0(11) . . . . ? 
N1 C1 N2 C4 177.7(9) . . . . ? 
C2 C3 N2 C1 -0.4(11) . . . . ? 
C2 C3 N2 C4 -177.2(9) . . . . ? 
C5 C4 N2 C1 133.6(10) . . . . ? 
C5 C4 N2 C3 -50.2(14) . . . . ? 
O1 C7 N3 C18 -176.4(9) . . . . ? 
C8 C7 N3 C18 4.0(13) . . . . ? 
O1 C7 N3 C6 5.9(14) . . . . ? 
C8 C7 N3 C6 -173.7(8) . . . . ? 
O2 C18 N3 C7 175.5(9) . . . . ? 
C17 C18 N3 C7 -5.3(13) . . . . ? 
O2 C18 N3 C6 -6.7(13) . . . . ? 
C17 C18 N3 C6 172.5(8) . . . . ? 
C5 C6 N3 C7 -105.4(10) . . . . ? 
C5 C6 N3 C18 76.6(11) . . . . ? 
 
_diffrn_measured_fraction_theta_max    0.990 
_diffrn_reflns_theta_full              25.24 
_diffrn_measured_fraction_theta_full   0.990 
_refine_diff_density_max    3.499 
_refine_diff_density_min   -2.987 
_refine_diff_density_rms    0.139 
