# Electronic Supplementary Material (ESI) for Dalton Transactions.
# This journal is © The Royal Society of Chemistry 2014

#######################################################################
#
#                 Cambridge Crystallographic Data Centre
#                                CCDC 
# 
#######################################################################
# 
#  This CIF contains data from an original supplementary publication
#  deposited with the CCDC, and may include chemical, crystal,
#  experimental, refinement, atomic coordinates,
#  anisotropic displacement parameters and molecular geometry data,
#  as required by the journal to which it was submitted.
#
#  This CIF is provided on the understanding that it is used for bona
#  fide research purposes only. It may contain copyright material
#  of the CCDC or of third parties, and may not be copied or further
#  disseminated in any form, whether machine-readable or not,
#  except for the purpose of generating routine backup copies
#  on your local computer system.
# 
#  For further information on the CCDC, data deposition and
#  data retrieval see:
#                         www.ccdc.cam.ac.uk
#
#  Bona fide researchers may freely download Mercury and enCIFer
#  from this site to visualise CIF-encoded structures and 
#  to carry out CIF format checking respectively.
#
data_z

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C15 H16 Cl2 N4 O Zn'
_chemical_formula_weight         404.59

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'
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'

_symmetry_cell_setting           Triclinic
_symmetry_space_group_name_H-M   'P-1   '

loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   7.5850(15)
_cell_length_b                   9.3580(19)
_cell_length_c                   13.408(3)
_cell_angle_alpha                99.77(3)
_cell_angle_beta                 94.79(3)
_cell_angle_gamma                108.62(3)
_cell_volume                     879.1(3)
_cell_formula_units_Z            2
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    8663
_cell_measurement_theta_min      3.03
_cell_measurement_theta_max      27.48

_exptl_crystal_description       block
_exptl_crystal_colour            red
_exptl_crystal_size_max          0.30
_exptl_crystal_size_mid          0.13
_exptl_crystal_size_min          0.05
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.528
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             412
_exptl_absorpt_coefficient_mu    1.708
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.6247
_exptl_absorpt_correction_T_max  0.9164
_exptl_absorpt_process_details   SADABS

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      293(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 Smart APEX CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         0
_diffrn_standards_interval_count 0
_diffrn_standards_interval_time  0
_diffrn_standards_decay_%        0
_diffrn_reflns_number            8663
_diffrn_reflns_av_R_equivalents  0.0593
_diffrn_reflns_av_sigmaI/netI    0.0827
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_theta_min         3.03
_diffrn_reflns_theta_max         27.48
_reflns_number_total             3967
_reflns_number_gt                2448
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'Bruker SMART'
_computing_cell_refinement       'Bruker SMART'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1997)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    SHELXP-97
_computing_publication_material  SHELXTL

_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)+(0.1000P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         3967
_refine_ls_number_parameters     209
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0970
_refine_ls_R_factor_gt           0.0515
_refine_ls_wR_factor_ref         0.1725
_refine_ls_wR_factor_gt          0.1399
_refine_ls_goodness_of_fit_ref   0.941
_refine_ls_restrained_S_all      0.941
_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
Zn1 Zn 0.33845(8) 0.44295(6) 0.70222(4) 0.0449(2) Uani 1 1 d . . .
Cl1 Cl 0.1131(2) 0.37585(18) 0.79663(11) 0.0678(4) Uani 1 1 d . . .
Cl2 Cl 0.49741(19) 0.27765(14) 0.67857(10) 0.0548(3) Uani 1 1 d . . .
O1 O 0.6319(6) 0.6937(4) 0.8842(3) 0.0650(10) Uani 1 1 d . . .
N1 N 0.5059(5) 0.6711(4) 0.7237(3) 0.0415(8) Uani 1 1 d . . .
N2 N 0.2613(5) 0.4829(4) 0.5593(3) 0.0382(8) Uani 1 1 d . . .
N3 N -0.2330(7) 0.0358(5) 0.2405(3) 0.0626(12) Uani 1 1 d . . .
H3A H -0.2437 0.0543 0.1801 0.075 Uiso 1 1 calc R . .
H3B H -0.2954 -0.0532 0.2514 0.075 Uiso 1 1 calc R . .
N4 N 0.2610(13) 0.8330(8) -0.0389(5) 0.112(2) Uani 1 1 d . . .
C1 C 0.4873(7) 0.7271(5) 0.6378(4) 0.0438(10) Uani 1 1 d . . .
C2 C 0.5915(8) 0.8759(6) 0.6328(4) 0.0572(13) Uani 1 1 d . . .
H2A H 0.5780 0.9122 0.5732 0.069 Uiso 1 1 calc R . .
C3 C 0.7162(8) 0.9704(6) 0.7176(5) 0.0622(15) Uani 1 1 d . . .
H3C H 0.7878 1.0709 0.7155 0.075 Uiso 1 1 calc R . .
C4 C 0.7330(8) 0.9152(6) 0.8033(5) 0.0588(13) Uani 1 1 d . . .
H4A H 0.8153 0.9776 0.8612 0.071 Uiso 1 1 calc R . .
C5 C 0.6251(7) 0.7631(5) 0.8040(4) 0.0484(11) Uani 1 1 d . . .
C6 C 0.3537(7) 0.6216(5) 0.5523(4) 0.0445(11) Uani 1 1 d . . .
H6A H 0.3345 0.6544 0.4918 0.053 Uiso 1 1 calc R . .
C7 C 0.7550(12) 0.7853(8) 0.9757(5) 0.089(2) Uani 1 1 d . . .
H7A H 0.7481 0.7241 1.0269 0.133 Uiso 1 1 calc R . .
H7B H 0.7177 0.8722 1.0004 0.133 Uiso 1 1 calc R . .
H7C H 0.8817 0.8210 0.9613 0.133 Uiso 1 1 calc R . .
C8 C 0.1346(7) 0.3761(5) 0.4776(3) 0.0395(10) Uani 1 1 d . . .
C9 C 0.1061(7) 0.4035(5) 0.3799(4) 0.0431(10) Uani 1 1 d . . .
H9A H 0.1709 0.4995 0.3669 0.052 Uiso 1 1 calc R . .
C10 C -0.0152(7) 0.2922(5) 0.3024(4) 0.0457(11) Uani 1 1 d . . .
H10A H -0.0297 0.3137 0.2376 0.055 Uiso 1 1 calc R . .
C11 C -0.1180(7) 0.1466(6) 0.3185(4) 0.0455(11) Uani 1 1 d . . .
C12 C -0.0930(8) 0.1202(6) 0.4178(4) 0.0532(13) Uani 1 1 d . . .
H12A H -0.1599 0.0251 0.4314 0.064 Uiso 1 1 calc R . .
C13 C 0.0276(7) 0.2314(5) 0.4946(4) 0.0458(11) Uani 1 1 d . . .
H13A H 0.0397 0.2113 0.5599 0.055 Uiso 1 1 calc R . .
C15 C 0.2708(11) 0.7417(9) 0.0025(5) 0.0771(18) Uani 1 1 d . . .
C14 C 0.2836(14) 0.6235(10) 0.0563(6) 0.111(3) Uani 1 1 d . . .
H14A H 0.3402 0.5727 0.0255 0.133 Uiso 1 1 calc R . .
H14B H 0.1589 0.5579 0.0601 0.133 Uiso 1 1 d R . .
H14 H 0.3382 0.6613 0.1150 0.133 Uiso 1 1 d R . .

loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_23
_atom_site_aniso_U_13
_atom_site_aniso_U_12
Zn1 0.0515(4) 0.0390(3) 0.0396(3) 0.0093(2) 0.0032(2) 0.0096(2)
Cl1 0.0746(9) 0.0730(9) 0.0546(8) 0.0212(7) 0.0235(7) 0.0160(8)
Cl2 0.0587(8) 0.0431(6) 0.0643(8) 0.0183(6) 0.0104(6) 0.0155(6)
O1 0.081(3) 0.049(2) 0.052(2) -0.0010(17) -0.020(2) 0.016(2)
N1 0.046(2) 0.0341(19) 0.041(2) 0.0014(17) 0.0026(17) 0.0130(17)
N2 0.046(2) 0.0334(18) 0.0338(18) 0.0043(15) 0.0077(17) 0.0120(16)
N3 0.074(3) 0.048(2) 0.048(3) 0.005(2) -0.003(2) 0.002(2)
N4 0.175(8) 0.089(5) 0.076(4) 0.011(4) -0.007(5) 0.061(5)
C1 0.044(2) 0.037(2) 0.049(3) 0.007(2) 0.011(2) 0.011(2)
C2 0.062(3) 0.042(3) 0.064(3) 0.013(3) 0.013(3) 0.011(2)
C3 0.060(3) 0.041(3) 0.074(4) 0.003(3) 0.013(3) 0.004(2)
C4 0.051(3) 0.043(3) 0.068(4) -0.007(3) -0.002(3) 0.009(2)
C5 0.053(3) 0.036(2) 0.051(3) -0.004(2) 0.002(2) 0.016(2)
C6 0.049(3) 0.042(3) 0.040(2) 0.008(2) 0.005(2) 0.013(2)
C7 0.110(6) 0.065(4) 0.070(4) 0.004(3) -0.039(4) 0.020(4)
C8 0.046(3) 0.035(2) 0.038(2) 0.0075(19) 0.009(2) 0.015(2)
C9 0.049(3) 0.037(2) 0.044(2) 0.012(2) 0.009(2) 0.014(2)
C10 0.054(3) 0.045(3) 0.037(2) 0.007(2) 0.009(2) 0.014(2)
C11 0.046(3) 0.043(3) 0.044(3) 0.004(2) 0.005(2) 0.012(2)
C12 0.064(3) 0.043(3) 0.049(3) 0.016(2) 0.009(3) 0.010(2)
C13 0.057(3) 0.037(2) 0.039(2) 0.012(2) 0.004(2) 0.009(2)
C15 0.096(5) 0.087(5) 0.050(3) 0.000(3) 0.001(3) 0.044(4)
C14 0.160(9) 0.120(7) 0.067(5) 0.032(5) 0.015(5) 0.059(7)

_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 N1 2.063(4) . ?
Zn1 N2 2.086(4) . ?
Zn1 Cl1 2.2056(15) . ?
Zn1 Cl2 2.2441(15) . ?
O1 C5 1.353(6) . ?
O1 C7 1.433(7) . ?
N1 C5 1.321(6) . ?
N1 C1 1.359(6) . ?
N2 C6 1.287(6) . ?
N2 C8 1.400(6) . ?
N3 C11 1.353(7) . ?
N3 H3A 0.8600 . ?
N3 H3B 0.8600 . ?
N4 C15 1.114(8) . ?
C1 C2 1.381(7) . ?
C1 C6 1.448(7) . ?
C2 C3 1.384(8) . ?
C2 H2A 0.9300 . ?
C3 C4 1.351(8) . ?
C3 H3C 0.9300 . ?
C4 C5 1.399(7) . ?
C4 H4A 0.9300 . ?
C6 H6A 0.9300 . ?
C7 H7A 0.9600 . ?
C7 H7B 0.9600 . ?
C7 H7C 0.9600 . ?
C8 C9 1.390(6) . ?
C8 C13 1.406(6) . ?
C9 C10 1.368(7) . ?
C9 H9A 0.9300 . ?
C10 C11 1.400(6) . ?
C10 H10A 0.9300 . ?
C11 C12 1.404(7) . ?
C12 C13 1.360(7) . ?
C12 H12A 0.9300 . ?
C13 H13A 0.9300 . ?
C15 C14 1.442(10) . ?
C14 H14A 0.8200 . ?
C14 H14B 0.9605 . ?
C14 H14 0.8211 . ?

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 Zn1 N2 81.39(15) . . ?
N1 Zn1 Cl1 119.62(11) . . ?
N2 Zn1 Cl1 116.74(11) . . ?
N1 Zn1 Cl2 113.73(11) . . ?
N2 Zn1 Cl2 107.58(10) . . ?
Cl1 Zn1 Cl2 113.43(6) . . ?
C5 O1 C7 117.0(5) . . ?
C5 N1 C1 118.6(4) . . ?
C5 N1 Zn1 130.3(3) . . ?
C1 N1 Zn1 111.1(3) . . ?
C6 N2 C8 122.3(4) . . ?
C6 N2 Zn1 110.7(3) . . ?
C8 N2 Zn1 126.9(3) . . ?
C11 N3 H3A 120.0 . . ?
C11 N3 H3B 120.0 . . ?
H3A N3 H3B 120.0 . . ?
N1 C1 C2 121.4(5) . . ?
N1 C1 C6 116.2(4) . . ?
C2 C1 C6 122.3(5) . . ?
C1 C2 C3 119.2(5) . . ?
C1 C2 H2A 120.4 . . ?
C3 C2 H2A 120.4 . . ?
C4 C3 C2 119.3(5) . . ?
C4 C3 H3C 120.3 . . ?
C2 C3 H3C 120.3 . . ?
C3 C4 C5 119.2(5) . . ?
C3 C4 H4A 120.4 . . ?
C5 C4 H4A 120.4 . . ?
N1 C5 O1 112.9(4) . . ?
N1 C5 C4 122.3(5) . . ?
O1 C5 C4 124.8(5) . . ?
N2 C6 C1 120.5(4) . . ?
N2 C6 H6A 119.7 . . ?
C1 C6 H6A 119.7 . . ?
O1 C7 H7A 109.5 . . ?
O1 C7 H7B 109.5 . . ?
H7A C7 H7B 109.5 . . ?
O1 C7 H7C 109.5 . . ?
H7A C7 H7C 109.5 . . ?
H7B C7 H7C 109.5 . . ?
C9 C8 N2 124.3(4) . . ?
C9 C8 C13 117.2(4) . . ?
N2 C8 C13 118.5(4) . . ?
C10 C9 C8 121.4(4) . . ?
C10 C9 H9A 119.3 . . ?
C8 C9 H9A 119.3 . . ?
C9 C10 C11 121.5(4) . . ?
C9 C10 H10A 119.3 . . ?
C11 C10 H10A 119.3 . . ?
N3 C11 C10 120.9(4) . . ?
N3 C11 C12 121.9(4) . . ?
C10 C11 C12 117.2(5) . . ?
C13 C12 C11 121.1(4) . . ?
C13 C12 H12A 119.5 . . ?
C11 C12 H12A 119.5 . . ?
C12 C13 C8 121.7(4) . . ?
C12 C13 H13A 119.2 . . ?
C8 C13 H13A 119.2 . . ?
N4 C15 C14 179.9(8) . . ?
C15 C14 H14A 109.5 . . ?
C15 C14 H14B 109.0 . . ?
H14A C14 H14B 109.9 . . ?
C15 C14 H14 111.0 . . ?
H14A C14 H14 109.7 . . ?
H14B C14 H14 107.8 . . ?

_diffrn_measured_fraction_theta_max 0.986
_diffrn_reflns_theta_full        27.48
_diffrn_measured_fraction_theta_full 0.986
_refine_diff_density_max         0.365
_refine_diff_density_min         -0.484
_refine_diff_density_rms         0.084
_database_code_depnum_ccdc_archive 'CCDC 980463'
#######################################################################
#
#                 Cambridge Crystallographic Data Centre
#                                CCDC 
# 
#######################################################################
# 
#  This CIF contains data from an original supplementary publication
#  deposited with the CCDC, and may include chemical, crystal,
#  experimental, refinement, atomic coordinates,
#  anisotropic displacement parameters and molecular geometry data,
#  as required by the journal to which it was submitted.
#
#  This CIF is provided on the understanding that it is used for bona
#  fide research purposes only. It may contain copyright material
#  of the CCDC or of third parties, and may not be copied or further
#  disseminated in any form, whether machine-readable or not,
#  except for the purpose of generating routine backup copies
#  on your local computer system.
# 
#  For further information on the CCDC, data deposition and
#  data retrieval see:
#                         www.ccdc.cam.ac.uk
#
#  Bona fide researchers may freely download Mercury and enCIFer
#  from this site to visualise CIF-encoded structures and 
#  to carry out CIF format checking respectively.
#
data_z

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C15 H16 Cl2 Hg N4 O'
_chemical_formula_weight         539.81

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           Triclinic
_symmetry_space_group_name_H-M   'P-1   '

loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   7.5770(15)
_cell_length_b                   9.3950(19)
_cell_length_c                   13.630(3)
_cell_angle_alpha                99.83(3)
_cell_angle_beta                 95.31(3)
_cell_angle_gamma                108.01(3)
_cell_volume                     898.2(3)
_cell_formula_units_Z            2
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    8876
_cell_measurement_theta_min      3.03
_cell_measurement_theta_max      27.48

_exptl_crystal_description       block
_exptl_crystal_colour            red
_exptl_crystal_size_max          0.11
_exptl_crystal_size_mid          0.11
_exptl_crystal_size_min          0.09
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.996
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             512
_exptl_absorpt_coefficient_mu    8.873
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.4311
_exptl_absorpt_correction_T_max  0.5124
_exptl_absorpt_process_details   SADABS

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      293(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 Smart APEX CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         0
_diffrn_standards_interval_count 0
_diffrn_standards_interval_time  0
_diffrn_standards_decay_%        0
_diffrn_reflns_number            8876
_diffrn_reflns_av_R_equivalents  0.0550
_diffrn_reflns_av_sigmaI/netI    0.0769
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_theta_min         3.03
_diffrn_reflns_theta_max         27.48
_reflns_number_total             4072
_reflns_number_gt                2646
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'Bruker SMART'
_computing_cell_refinement       'Bruker SMART'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1997)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    SHELXP-97
_computing_publication_material  SHELXTL

_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)+(0.1000P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         4072
_refine_ls_number_parameters     209
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0866
_refine_ls_R_factor_gt           0.0505
_refine_ls_wR_factor_ref         0.1666
_refine_ls_wR_factor_gt          0.1367
_refine_ls_goodness_of_fit_ref   0.963
_refine_ls_restrained_S_all      0.963
_refine_ls_shift/su_max          0.039
_refine_ls_shift/su_mean         0.001

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
Hg1 Hg 0.32916(6) -0.06209(5) 0.71078(3) 0.0644(2) Uani 1 1 d . . .
O1 O 0.6378(12) 0.2107(9) 0.8753(6) 0.076(2) Uani 1 1 d . . .
N1 N 0.5127(10) 0.1846(9) 0.7166(7) 0.0513(18) Uani 1 1 d . . .
N2 N 0.2650(11) -0.0091(9) 0.5508(6) 0.0472(17) Uani 1 1 d . . .
N3 N -0.2397(15) -0.4487(12) 0.2330(8) 0.080(3) Uani 1 1 d . . .
H3A H -0.3026 -0.5382 0.2411 0.096 Uiso 1 1 calc R . .
H3B H -0.2515 -0.4256 0.1749 0.096 Uiso 1 1 calc R . .
N4 N 0.260(3) 0.3229(19) 0.9658(11) 0.124(5) Uani 1 1 d . . .
C1 C 0.4920(14) 0.2309(11) 0.6293(8) 0.055(2) Uani 1 1 d . . .
C2 C 0.5964(16) 0.3778(14) 0.6218(9) 0.066(3) Uani 1 1 d . . .
H2A H 0.5823 0.4101 0.5616 0.079 Uiso 1 1 calc R . .
C3 C 0.7179(16) 0.4735(13) 0.7019(10) 0.069(3) Uani 1 1 d . . .
H3C H 0.7885 0.5718 0.6969 0.083 Uiso 1 1 calc R . .
C4 C 0.7374(15) 0.4257(13) 0.7908(11) 0.072(3) Uani 1 1 d . . .
H4A H 0.8181 0.4914 0.8473 0.086 Uiso 1 1 calc R . .
C5 C 0.6332(13) 0.2764(11) 0.7941(9) 0.059(3) Uani 1 1 d . . .
C6 C 0.3576(14) 0.1254(11) 0.5443(7) 0.054(2) Uani 1 1 d . . .
H6A H 0.3397 0.1576 0.4844 0.065 Uiso 1 1 calc R . .
C7 C 0.770(2) 0.3045(16) 0.9658(11) 0.104(5) Uani 1 1 d . . .
H7A H 0.7618 0.2468 1.0180 0.156 Uiso 1 1 calc R . .
H7B H 0.7390 0.3951 0.9885 0.156 Uiso 1 1 calc R . .
H7C H 0.8955 0.3330 0.9502 0.156 Uiso 1 1 calc R . .
C8 C 0.1354(13) -0.1143(10) 0.4690(7) 0.0455(19) Uani 1 1 d . . .
C9 C 0.1078(14) -0.0866(11) 0.3739(8) 0.055(2) Uani 1 1 d . . .
H9A H 0.1742 0.0080 0.3612 0.066 Uiso 1 1 calc R . .
C10 C -0.0179(14) -0.1978(11) 0.2965(7) 0.052(2) Uani 1 1 d . . .
H10A H -0.0346 -0.1764 0.2328 0.063 Uiso 1 1 calc R . .
C11 C -0.1201(14) -0.3423(11) 0.3132(7) 0.051(2) Uani 1 1 d . . .
C12 C -0.0924(14) -0.3700(13) 0.4102(8) 0.059(2) Uani 1 1 d . . .
H12A H -0.1580 -0.4645 0.4234 0.070 Uiso 1 1 calc R . .
C13 C 0.0322(14) -0.2576(11) 0.4867(8) 0.056(2) Uani 1 1 d . . .
H13A H 0.0480 -0.2773 0.5509 0.067 Uiso 1 1 calc R . .
Cl1 Cl 0.0946(5) -0.1449(4) 0.8124(3) 0.0893(10) Uani 1 1 d . . .
Cl2 Cl 0.5001(4) -0.2459(3) 0.6779(2) 0.0678(7) Uani 1 1 d . . .
C14 C 0.308(3) 0.117(2) 1.0600(13) 0.114(6) Uani 1 1 d . . .
H14A H 0.2277 0.0340 1.0358 0.137 Uiso 1 1 calc R . .
H14B H 0.4256 0.1036 1.0480 0.137 Uiso 1 1 d R . .
H14C H 0.3039 0.1406 1.1204 0.137 Uiso 1 1 d R . .
C15 C 0.277(2) 0.233(2) 1.0071(10) 0.090(4) Uani 1 1 d . . .

loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_23
_atom_site_aniso_U_13
_atom_site_aniso_U_12
Hg1 0.0739(3) 0.0498(3) 0.0620(3) 0.01465(19) 0.0012(2) 0.01126(19)
O1 0.092(5) 0.057(5) 0.064(5) 0.005(4) -0.021(4) 0.016(4)
N1 0.042(4) 0.038(4) 0.070(5) 0.003(4) 0.005(4) 0.012(3)
N2 0.052(4) 0.044(4) 0.045(4) 0.007(3) 0.003(3) 0.016(3)
N3 0.093(7) 0.050(6) 0.069(6) 0.002(5) -0.009(6) -0.005(5)
N4 0.200(17) 0.099(11) 0.088(9) 0.017(8) 0.020(10) 0.075(12)
C1 0.053(5) 0.041(5) 0.067(6) 0.005(5) 0.012(5) 0.013(4)
C2 0.067(6) 0.057(7) 0.064(6) 0.001(5) 0.010(6) 0.014(5)
C3 0.069(7) 0.040(6) 0.091(8) 0.007(6) 0.024(7) 0.008(5)
C4 0.055(6) 0.044(6) 0.099(9) -0.009(6) 0.006(6) 0.006(5)
C5 0.048(5) 0.037(5) 0.084(7) -0.007(5) 0.001(5) 0.017(4)
C6 0.067(6) 0.040(5) 0.052(5) 0.009(4) 0.005(5) 0.013(4)
C7 0.128(12) 0.057(8) 0.087(9) -0.004(7) -0.062(9) 0.006(8)
C8 0.051(5) 0.041(5) 0.047(5) 0.014(4) 0.010(4) 0.016(4)
C9 0.054(5) 0.037(5) 0.071(6) 0.013(5) 0.017(5) 0.006(4)
C10 0.064(6) 0.046(5) 0.044(5) 0.005(4) 0.003(4) 0.019(4)
C11 0.060(5) 0.049(5) 0.046(5) 0.003(4) 0.009(4) 0.027(4)
C12 0.058(5) 0.052(6) 0.069(6) 0.020(5) 0.011(5) 0.017(5)
C13 0.059(5) 0.042(5) 0.059(6) 0.013(4) 0.003(5) 0.008(4)
Cl1 0.098(2) 0.084(2) 0.079(2) 0.0238(18) 0.0240(19) 0.0146(18)
Cl2 0.0777(16) 0.0491(14) 0.0801(17) 0.0219(13) 0.0174(15) 0.0201(12)
C14 0.165(17) 0.113(14) 0.082(10) 0.025(9) 0.023(11) 0.066(13)
C15 0.111(11) 0.089(11) 0.061(7) -0.007(7) -0.014(7) 0.042(9)

_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 2.288(8) . ?
Hg1 N2 2.358(7) . ?
Hg1 Cl1 2.377(3) . ?
Hg1 Cl2 2.467(3) . ?
O1 C5 1.358(14) . ?
O1 C7 1.468(14) . ?
N1 C5 1.310(13) . ?
N1 C1 1.347(14) . ?
N2 C6 1.265(12) . ?
N2 C8 1.416(12) . ?
N3 C11 1.378(13) . ?
N3 H3A 0.8600 . ?
N3 H3B 0.8600 . ?
N4 C15 1.13(2) . ?
C1 C2 1.389(15) . ?
C1 C6 1.458(14) . ?
C2 C3 1.347(17) . ?
C2 H2A 0.9300 . ?
C3 C4 1.374(18) . ?
C3 H3C 0.9300 . ?
C4 C5 1.392(15) . ?
C4 H4A 0.9300 . ?
C6 H6A 0.9300 . ?
C7 H7A 0.9600 . ?
C7 H7B 0.9600 . ?
C7 H7C 0.9600 . ?
C8 C9 1.375(13) . ?
C8 C13 1.406(12) . ?
C9 C10 1.391(14) . ?
C9 H9A 0.9300 . ?
C10 C11 1.408(14) . ?
C10 H10A 0.9300 . ?
C11 C12 1.400(14) . ?
C12 C13 1.385(15) . ?
C12 H12A 0.9300 . ?
C13 H13A 0.9300 . ?
C14 C15 1.46(2) . ?
C14 H14A 0.8200 . ?
C14 H14B 0.9606 . ?
C14 H14C 0.8212 . ?

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 N2 73.0(3) . . ?
N1 Hg1 Cl1 126.8(2) . . ?
N2 Hg1 Cl1 123.5(2) . . ?
N1 Hg1 Cl2 112.65(19) . . ?
N2 Hg1 Cl2 103.3(2) . . ?
Cl1 Hg1 Cl2 111.06(12) . . ?
C5 O1 C7 116.7(10) . . ?
C5 N1 C1 120.4(9) . . ?
C5 N1 Hg1 125.8(8) . . ?
C1 N1 Hg1 113.7(6) . . ?
C6 N2 C8 122.1(8) . . ?
C6 N2 Hg1 113.3(7) . . ?
C8 N2 Hg1 124.6(6) . . ?
C11 N3 H3A 120.0 . . ?
C11 N3 H3B 120.0 . . ?
H3A N3 H3B 120.0 . . ?
N1 C1 C2 119.9(10) . . ?
N1 C1 C6 119.0(9) . . ?
C2 C1 C6 121.1(10) . . ?
C3 C2 C1 119.9(12) . . ?
C3 C2 H2A 120.1 . . ?
C1 C2 H2A 120.1 . . ?
C2 C3 C4 119.9(11) . . ?
C2 C3 H3C 120.1 . . ?
C4 C3 H3C 120.1 . . ?
C3 C4 C5 118.2(11) . . ?
C3 C4 H4A 120.9 . . ?
C5 C4 H4A 120.9 . . ?
N1 C5 O1 112.6(9) . . ?
N1 C5 C4 121.6(12) . . ?
O1 C5 C4 125.7(11) . . ?
N2 C6 C1 121.0(9) . . ?
N2 C6 H6A 119.5 . . ?
C1 C6 H6A 119.5 . . ?
O1 C7 H7A 109.5 . . ?
O1 C7 H7B 109.5 . . ?
H7A C7 H7B 109.5 . . ?
O1 C7 H7C 109.5 . . ?
H7A C7 H7C 109.5 . . ?
H7B C7 H7C 109.5 . . ?
C9 C8 C13 118.4(9) . . ?
C9 C8 N2 124.4(8) . . ?
C13 C8 N2 117.1(8) . . ?
C8 C9 C10 121.0(9) . . ?
C8 C9 H9A 119.5 . . ?
C10 C9 H9A 119.5 . . ?
C9 C10 C11 121.0(9) . . ?
C9 C10 H10A 119.5 . . ?
C11 C10 H10A 119.5 . . ?
N3 C11 C12 123.8(10) . . ?
N3 C11 C10 118.2(9) . . ?
C12 C11 C10 118.0(9) . . ?
C13 C12 C11 120.3(10) . . ?
C13 C12 H12A 119.8 . . ?
C11 C12 H12A 119.8 . . ?
C12 C13 C8 121.3(9) . . ?
C12 C13 H13A 119.4 . . ?
C8 C13 H13A 119.4 . . ?
C15 C14 H14A 109.5 . . ?
C15 C14 H14B 109.5 . . ?
H14A C14 H14B 105.4 . . ?
C15 C14 H14C 110.9 . . ?
H14A C14 H14C 109.2 . . ?
H14B C14 H14C 112.1 . . ?
N4 C15 C14 177(2) . . ?

_diffrn_measured_fraction_theta_max 0.989
_diffrn_reflns_theta_full        27.48
_diffrn_measured_fraction_theta_full 0.989
_refine_diff_density_max         0.910
_refine_diff_density_min         -1.548
_refine_diff_density_rms         0.160
_database_code_depnum_ccdc_archive 'CCDC 980464'
