# Electronic Supplementary Material (ESI) for Dalton Transactions.
# This journal is © The Royal Society of Chemistry 2016

  
data_1 
  
_audit_creation_method            SHELXL-97 
_chemical_name_systematic 
; 
 ? 
; 
_chemical_name_common             ? 
_chemical_melting_point           ? 
_chemical_formula_moiety          ? 
_chemical_formula_sum 
 'C16 H14.67 K1.33 N5.33 O5.33' 
_chemical_formula_weight          419.13 
  
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' 
 'K'  'K'   0.2009   0.2494 
 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 
  
_symmetry_cell_setting            Monoclinic 
_symmetry_space_group_name_H-M    P2(1)/c 
  
loop_ 
 _symmetry_equiv_pos_as_xyz 
 'x, y, z' 
 '-x, y+1/2, -z+1/2' 
 '-x, -y, -z' 
 'x, -y-1/2, z-1/2' 
  
_cell_length_a                    8.135(8) 
_cell_length_b                    11.441(12) 
_cell_length_c                    14.604(15) 
_cell_angle_alpha                 90.00 
_cell_angle_beta                  98.293(17) 
_cell_angle_gamma                 90.00 
_cell_volume                      1345(2) 
_cell_formula_units_Z             3 
_cell_measurement_temperature     296(2) 
_cell_measurement_reflns_used     3258 
_cell_measurement_theta_min       2.27 
_cell_measurement_theta_max       27.37 
  
_exptl_crystal_description        bulk 
_exptl_crystal_colour             yellow 
_exptl_crystal_size_max           0.43 
_exptl_crystal_size_mid           0.40 
_exptl_crystal_size_min           0.26 
_exptl_crystal_density_meas       ?
_exptl_crystal_density_diffrn     1.552 
_exptl_crystal_density_method     'not measured' 
_exptl_crystal_F_000              648 
_exptl_absorpt_coefficient_mu     0.417 
_exptl_absorpt_correction_type    Multi-scan 
_exptl_absorpt_correction_T_min   0.8409 
_exptl_absorpt_correction_T_max   0.8992 
_exptl_absorpt_process_details    SADABS 
  
_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   'CCD area detector' 
_diffrn_measurement_method        'phi and omega scans' 
_diffrn_detector_area_resol_mean  ? 
_diffrn_standards_number          ? 
_diffrn_standards_interval_count  ? 
_diffrn_standards_interval_time   ? 
_diffrn_standards_decay_%         ? 
_diffrn_reflns_number             8717 
_diffrn_reflns_av_R_equivalents   0.0414 
_diffrn_reflns_av_sigmaI/netI     0.0438 
_diffrn_reflns_limit_h_min        -10 
_diffrn_reflns_limit_h_max        8 
_diffrn_reflns_limit_k_min        -14 
_diffrn_reflns_limit_k_max        14 
_diffrn_reflns_limit_l_min        -19 
_diffrn_reflns_limit_l_max        19 
_diffrn_reflns_theta_min          2.27 
_diffrn_reflns_theta_max          27.64 
_reflns_number_total              3098 
_reflns_number_gt                 2534 
_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, 1990)' 
_computing_structure_refinement   'SHELXL-97 (Sheldrick, 1997)' 
_computing_molecular_graphics     'Bruker SHELXTL' 
_computing_publication_material   'Bruker 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)+(0.1310P)²+1.1644P] 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          3098 
_refine_ls_number_parameters      199 
_refine_ls_number_restraints      0 
_refine_ls_R_factor_all           0.0735 
_refine_ls_R_factor_gt            0.0630 
_refine_ls_wR_factor_ref          0.2112 
_refine_ls_wR_factor_gt           0.1997 
_refine_ls_goodness_of_fit_ref    1.060 
_refine_ls_restrained_S_all       1.060 
_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 
C5 C 1.1961(4) 0.5992(3) 0.1174(2) 0.0327(6) Uani 1 1 d . . . 
C7 C 0.5623(3) 0.7951(2) 0.14972(17) 0.0240(5) Uani 1 1 d . . . 
C8 C 1.0280(3) 0.7631(2) 0.06748(16) 0.0239(5) Uani 1 1 d . . . 
C9 C 0.6385(3) 0.7948(2) 0.24826(18) 0.0285(6) Uani 1 1 d . . . 
C11 C 0.9270(3) 0.8172(3) -0.01555(18) 0.0290(6) Uani 1 1 d . . . 
C13 C 1.0465(3) 0.8078(2) 0.15762(17) 0.0264(5) Uani 1 1 d . . . 
C15 C 0.4518(3) 0.8811(2) 0.1082(2) 0.0290(6) Uani 1 1 d . . . 
C17 C 0.4462(4) 0.7790(3) -0.0368(2) 0.0373(7) Uani 1 1 d . . . 
H17 H 0.4080 0.7729 -0.0998 0.045 Uiso 1 1 calc R . . 
C18 C 1.2149(4) 0.6393(3) 0.2082(2) 0.0362(6) Uani 1 1 d . . . 
H18 H 1.2767 0.5965 0.2552 0.043 Uiso 1 1 calc R . . 
C19 C 0.5522(4) 0.6954(3) 0.00662(19) 0.0327(6) Uani 1 1 d . . . 
C20 C 0.3977(4) 0.8702(3) 0.0123(2) 0.0353(6) Uani 1 1 d . . . 
H20 H 0.3274 0.9267 -0.0177 0.042 Uiso 1 1 calc R . . 
C2A C 1.1422(3) 0.7417(3) 0.22767(18) 0.0324(6) Uani 1 1 d . . . 
H2A H 1.1558 0.7687 0.2884 0.039 Uiso 1 1 calc R . . 
K1 K 0.80255(10) 0.48007(6) 0.11594(5) 0.0440(3) Uani 1 1 d . . . 
N1 N 0.6065(3) 0.70644(19) 0.09672(15) 0.0262(5) Uani 1 1 d . . . 
N2 N 1.1054(3) 0.66149(19) 0.05213(15) 0.0275(5) Uani 1 1 d . . . 
N4 N 0.4002(4) 0.9714(2) 0.1554(2) 0.0425(7) Uani 1 1 d . . . 
H4A H 0.4346 0.9786 0.2136 0.051 Uiso 1 1 calc R . . 
H4B H 0.3326 1.0220 0.1274 0.051 Uiso 1 1 calc R . . 
N1A N 0.9762(3) 0.9097(2) 0.17901(18) 0.0403(6) Uani 1 1 d . . . 
H1A1 H 0.9174 0.9497 0.1364 0.048 Uiso 1 1 calc R . . 
H1A2 H 0.9903 0.9344 0.2352 0.048 Uiso 1 1 calc R . . 
O1 O 0.8453(3) 0.9051(2) -0.00691(15) 0.0428(6) Uani 1 1 d . . . 
O2 O 0.9353(3) 0.7610(3) -0.08963(15) 0.0550(7) Uani 1 1 d . . . 
O3 O 0.7345(3) 0.70614(18) 0.27016(14) 0.0389(5) Uani 1 1 d . . . 
H3 H 0.8025 0.7225 0.3154 0.058 Uiso 1 1 calc R . . 
O4 O 0.6072(3) 0.8738(2) 0.29962(15) 0.0433(6) Uani 1 1 d . . . 
H1AA H 1.248(5) 0.534(4) 0.104(3) 0.044(10) Uiso 1 1 d . . . 
H3AA H 0.582(4) 0.636(3) -0.022(3) 0.038(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 
C5 N2 1.326(4) . ? 
C5 C18 1.390(4) . ? 
C5 K1 3.528(4) 3_765 ? 
C5 H1AA 0.90(4) . ? 
C7 N1 1.355(3) . ? 
C7 C15 1.410(4) . ? 
C7 C9 1.482(4) . ? 
C8 N2 1.356(3) . ? 
C8 C13 1.400(4) . ? 
C8 C11 1.497(4) . ? 
C9 O4 1.224(4) . ? 
C9 O3 1.292(4) . ? 
C11 O1 1.222(4) . ? 
C11 O2 1.269(4) . ? 
C13 N1A 1.354(4) . ? 
C13 C2A 1.412(4) . ? 
C15 N4 1.342(4) . ? 
C15 C20 1.411(4) . ? 
C17 C20 1.357(4) . ? 
C17 C19 1.379(4) . ? 
C17 H17 0.9300 . ? 
C18 C2A 1.361(4) . ? 
C18 H18 0.9300 . ? 
C19 N1 1.332(4) . ? 
C19 H3AA 0.85(4) . ? 
C20 H20 0.9300 . ? 
C2A H2A 0.9300 . ? 
K1 N1 3.033(3) . ? 
K1 N2 3.121(3) 3_765 ? 
K1 N1A 3.362(4) 2_745 ? 
K1 N2 3.451(3) . ? 
K1 C5 3.528(4) 3_765 ? 
K1 K1 5.013(4) 3_765 ? 
K1 H3AA 3.07(4) . ? 
N2 K1 3.121(3) 3_765 ? 
N4 H4A 0.8600 . ? 
N4 H4B 0.8600 . ? 
N1A K1 3.362(4) 2_755 ? 
N1A H1A1 0.8600 . ? 
N1A H1A2 0.8600 . ? 
O3 H3 0.8200 . ? 
  
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 
N2 C5 C18 118.8(3) . . ? 
N2 C5 K1 61.49(16) . 3_765 ? 
C18 C5 K1 172.2(2) . 3_765 ? 
N2 C5 H1AA 122(3) . . ? 
C18 C5 H1AA 119(3) . . ? 
K1 C5 H1AA 61(3) 3_765 . ? 
N1 C7 C15 118.8(2) . . ? 
N1 C7 C9 116.4(2) . . ? 
C15 C7 C9 124.8(2) . . ? 
N2 C8 C13 118.6(2) . . ? 
N2 C8 C11 115.7(2) . . ? 
C13 C8 C11 125.6(2) . . ? 
O4 C9 O3 126.8(3) . . ? 
O4 C9 C7 119.9(3) . . ? 
O3 C9 C7 113.2(2) . . ? 
O1 C11 O2 127.0(3) . . ? 
O1 C11 C8 120.0(2) . . ? 
O2 C11 C8 113.0(2) . . ? 
N1A C13 C8 122.7(2) . . ? 
N1A C13 C2A 120.0(2) . . ? 
C8 C13 C2A 117.3(2) . . ? 
N4 C15 C7 122.9(3) . . ? 
N4 C15 C20 120.1(3) . . ? 
C7 C15 C20 117.0(2) . . ? 
C20 C17 C19 120.0(3) . . ? 
C20 C17 H17 120.0 . . ? 
C19 C17 H17 120.0 . . ? 
C2A C18 C5 119.5(3) . . ? 
C2A C18 H18 120.2 . . ? 
C5 C18 H18 120.2 . . ? 
N1 C19 C17 119.0(3) . . ? 
N1 C19 H3AA 119(3) . . ? 
C17 C19 H3AA 122(3) . . ? 
C17 C20 C15 121.3(3) . . ? 
C17 C20 H20 119.4 . . ? 
C15 C20 H20 119.4 . . ? 
C18 C2A C13 121.4(3) . . ? 
C18 C2A H2A 119.3 . . ? 
C13 C2A H2A 119.3 . . ? 
N1 K1 N2 123.57(7) . 3_765 ? 
N1 K1 N1A 119.59(7) . 2_745 ? 
N2 K1 N1A 114.70(9) 3_765 2_745 ? 
N1 K1 N2 81.25(9) . . ? 
N2 K1 N2 80.68(8) 3_765 . ? 
N1A K1 N2 94.20(8) 2_745 . ? 
N1 K1 C5 101.83(7) . 3_765 ? 
N2 K1 C5 21.93(6) 3_765 3_765 ? 
N1A K1 C5 136.31(9) 2_745 3_765 ? 
N2 K1 C5 78.00(7) . 3_765 ? 
N1 K1 K1 103.86(6) . 3_765 ? 
N2 K1 K1 42.79(6) 3_765 3_765 ? 
N1A K1 K1 108.09(9) 2_745 3_765 ? 
N2 K1 K1 37.90(5) . 3_765 ? 
C5 K1 K1 43.90(6) 3_765 3_765 ? 
N1 K1 H3AA 36.3(7) . . ? 
N2 K1 H3AA 88.2(7) 3_765 . ? 
N1A K1 H3AA 155.7(7) 2_745 . ? 
N2 K1 H3AA 81.1(7) . . ? 
C5 K1 H3AA 66.3(7) 3_765 . ? 
K1 K1 H3AA 82.8(7) 3_765 . ? 
C19 N1 C7 123.9(2) . . ? 
C19 N1 K1 96.06(17) . . ? 
C7 N1 K1 139.92(17) . . ? 
C5 N2 C8 124.4(2) . . ? 
C5 N2 K1 96.58(18) . 3_765 ? 
C8 N2 K1 138.13(16) . 3_765 ? 
C5 N2 K1 80.08(18) . . ? 
C8 N2 K1 95.99(16) . . ? 
K1 N2 K1 99.32(8) 3_765 . ? 
C15 N4 H4A 120.0 . . ? 
C15 N4 H4B 120.0 . . ? 
H4A N4 H4B 120.0 . . ? 
C13 N1A K1 102.83(17) . 2_755 ? 
C13 N1A H1A1 120.0 . . ? 
K1 N1A H1A1 133.4 2_755 . ? 
C13 N1A H1A2 120.0 . . ? 
K1 N1A H1A2 24.5 2_755 . ? 
H1A1 N1A H1A2 120.0 . . ? 
C9 O3 H3 109.5 . . ? 
  
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 C7 C9 O4 178.3(2) . . . . ? 
C15 C7 C9 O4 -0.4(4) . . . . ? 
N1 C7 C9 O3 -1.9(3) . . . . ? 
C15 C7 C9 O3 179.4(2) . . . . ? 
N2 C8 C11 O1 175.7(3) . . . . ? 
C13 C8 C11 O1 -3.6(4) . . . . ? 
N2 C8 C11 O2 -2.8(4) . . . . ? 
C13 C8 C11 O2 177.9(3) . . . . ? 
N2 C8 C13 N1A 178.8(3) . . . . ? 
C11 C8 C13 N1A -1.9(4) . . . . ? 
N2 C8 C13 C2A -1.6(4) . . . . ? 
C11 C8 C13 C2A 177.7(2) . . . . ? 
N1 C7 C15 N4 179.4(2) . . . . ? 
C9 C7 C15 N4 -1.9(4) . . . . ? 
N1 C7 C15 C20 -1.7(4) . . . . ? 
C9 C7 C15 C20 177.0(2) . . . . ? 
N2 C5 C18 C2A -0.9(5) . . . . ? 
K1 C5 C18 C2A 88.8(15) 3_765 . . . ? 
C20 C17 C19 N1 -0.5(5) . . . . ? 
C19 C17 C20 C15 -0.8(5) . . . . ? 
N4 C15 C20 C17 -179.1(3) . . . . ? 
C7 C15 C20 C17 1.9(4) . . . . ? 
C5 C18 C2A C13 0.6(5) . . . . ? 
N1A C13 C2A C18 -179.7(3) . . . . ? 
C8 C13 C2A C18 0.6(4) . . . . ? 
C17 C19 N1 C7 0.8(4) . . . . ? 
C17 C19 N1 K1 177.3(3) . . . . ? 
C15 C7 N1 C19 0.4(4) . . . . ? 
C9 C7 N1 C19 -178.4(3) . . . . ? 
C15 C7 N1 K1 -174.33(18) . . . . ? 
C9 C7 N1 K1 6.9(4) . . . . ? 
N2 K1 N1 C19 14.7(2) 3_765 . . . ? 
N1A K1 N1 C19 177.19(17) 2_745 . . . ? 
N2 K1 N1 C19 87.32(18) . . . . ? 
C5 K1 N1 C19 11.63(19) 3_765 . . . ? 
K1 K1 N1 C19 56.67(18) 3_765 . . . ? 
N2 K1 N1 C7 -169.7(2) 3_765 . . . ? 
N1A K1 N1 C7 -7.2(3) 2_745 . . . ? 
N2 K1 N1 C7 -97.1(3) . . . . ? 
C5 K1 N1 C7 -172.8(2) 3_765 . . . ? 
K1 K1 N1 C7 -127.8(3) 3_765 . . . ? 
C18 C5 N2 C8 -0.1(4) . . . . ? 
K1 C5 N2 C8 -171.2(3) 3_765 . . . ? 
C18 C5 N2 K1 171.1(3) . . . 3_765 ? 
C18 C5 N2 K1 -90.6(3) . . . . ? 
K1 C5 N2 K1 98.35(8) 3_765 . . . ? 
C13 C8 N2 C5 1.4(4) . . . . ? 
C11 C8 N2 C5 -178.0(3) . . . . ? 
C13 C8 N2 K1 -165.42(18) . . . 3_765 ? 
C11 C8 N2 K1 15.2(4) . . . 3_765 ? 
C13 C8 N2 K1 83.4(2) . . . . ? 
C11 C8 N2 K1 -95.9(2) . . . . ? 
N1 K1 N2 C5 138.57(17) . . . . ? 
N2 K1 N2 C5 -95.12(18) 3_765 . . . ? 
N1A K1 N2 C5 19.25(17) 2_745 . . . ? 
C5 K1 N2 C5 -117.27(16) 3_765 . . . ? 
K1 K1 N2 C5 -95.12(18) 3_765 . . . ? 
N1 K1 N2 C8 14.58(14) . . . . ? 
N2 K1 N2 C8 140.90(17) 3_765 . . . ? 
N1A K1 N2 C8 -104.73(15) 2_745 . . . ? 
C5 K1 N2 C8 118.75(15) 3_765 . . . ? 
K1 K1 N2 C8 140.90(17) 3_765 . . . ? 
N1 K1 N2 K1 -126.31(8) . . . 3_765 ? 
N2 K1 N2 K1 0.0 3_765 . . 3_765 ? 
N1A K1 N2 K1 114.37(9) 2_745 . . 3_765 ? 
C5 K1 N2 K1 -22.15(6) 3_765 . . 3_765 ? 
C8 C13 N1A K1 -161.1(2) . . . 2_755 ? 
C2A C13 N1A K1 19.3(3) . . . 2_755 ? 
  
_diffrn_measured_fraction_theta_max    0.985 
_diffrn_reflns_theta_full              27.64 
_diffrn_measured_fraction_theta_full   0.985 
_refine_diff_density_max    0.695 
_refine_diff_density_min   -0.715 
_refine_diff_density_rms    0.104 

#===end

data_2 
  
_audit_creation_method            SHELXL-97 
_chemical_name_systematic 
; 
 ? 
; 
_chemical_name_common             ? 
_chemical_melting_point           ? 
_chemical_formula_moiety          ? 
_chemical_formula_sum 
 'C24 H22 N8 O10 Zn2' 
_chemical_formula_weight          713.24 
  
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' 
 'Zn'  'Zn'   0.2839   1.4301 
 '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                    10.017(3) 
_cell_length_b                    10.064(3) 
_cell_length_c                    13.150(4) 
_cell_angle_alpha                 90.00 
_cell_angle_beta                  89.992(5) 
_cell_angle_gamma                 90.00 
_cell_volume                      1325.6(6) 
_cell_formula_units_Z             2 
_cell_measurement_temperature     296(2) 
_cell_measurement_reflns_used     2355 
_cell_measurement_theta_min       2.87 
_cell_measurement_theta_max       27.32 
  
_exptl_crystal_description        bulk 
_exptl_crystal_colour             yellow 
_exptl_crystal_size_max           0.38 
_exptl_crystal_size_mid           0.25 
_exptl_crystal_size_min           0.19 
_exptl_crystal_density_meas       ? 
_exptl_crystal_density_diffrn     1.787 
_exptl_crystal_density_method     'not measured' 
_exptl_crystal_F_000              724 
_exptl_absorpt_coefficient_mu     1.885 
_exptl_absorpt_correction_type    Multi-scan 
_exptl_absorpt_correction_T_min   0.5345 
_exptl_absorpt_correction_T_max   0.7159 
_exptl_absorpt_process_details    SADABS 
  
_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   'Bruker APEX-II CCD' 
_diffrn_measurement_method        'φ and ω scans' 
_diffrn_detector_area_resol_mean  ? 
_diffrn_standards_number          0 
_diffrn_standards_interval_count  ? 
_diffrn_standards_interval_time   ? 
_diffrn_standards_decay_%         ? 
_diffrn_reflns_number             4212 
_diffrn_reflns_av_R_equivalents   0.0222 
_diffrn_reflns_av_sigmaI/netI     0.0250 
_diffrn_reflns_limit_h_min        -12 
_diffrn_reflns_limit_h_max        12 
_diffrn_reflns_limit_k_min        -13 
_diffrn_reflns_limit_k_max        8 
_diffrn_reflns_limit_l_min        -17 
_diffrn_reflns_limit_l_max        17 
_diffrn_reflns_theta_min          2.87 
_diffrn_reflns_theta_max          27.53 
_reflns_number_total              1523 
_reflns_number_gt                 1403 
_reflns_threshold_expression      >2sigma(I) 
  
_computing_data_collection        'Bruker APEX2' 
_computing_cell_refinement        'Bruker SAINT' 
_computing_data_reduction         'Bruker SAINT' 
_computing_structure_solution     'SHELXS-97 (Sheldrick, 1990)' 
_computing_structure_refinement   'SHELXL-97 (Sheldrick, 1997)' 
_computing_molecular_graphics     'Bruker SHELXTL' 
_computing_publication_material   'Bruker 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)+(0.0475P)²+0.6179P] 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          1523 
_refine_ls_number_parameters      102 
_refine_ls_number_restraints      0 
_refine_ls_R_factor_all           0.0296 
_refine_ls_R_factor_gt            0.0269 
_refine_ls_wR_factor_ref          0.0835 
_refine_ls_wR_factor_gt           0.0816 
_refine_ls_goodness_of_fit_ref    1.150 
_refine_ls_restrained_S_all       1.150 
_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 
C3 C -0.0467(3) 0.2161(2) -0.08101(18) 0.0382(5) Uani 1 1 d . . . 
H3 H -0.1069 0.2474 -0.1292 0.046 Uiso 1 1 calc R . . 
C5 C -0.0694(2) 0.2373(2) 0.02218(17) 0.0338(5) Uani 1 1 d . . . 
H5 H -0.1462 0.2819 0.0426 0.041 Uiso 1 1 calc R . . 
C7 C 0.12848(19) 0.12996(19) 0.06466(15) 0.0264(4) Uani 1 1 d . . . 
C8 C 0.21652(19) 0.0903(2) 0.15200(16) 0.0308(4) Uani 1 1 d . . . 
C10 C 0.1577(2) 0.1034(2) -0.03805(16) 0.0301(4) Uani 1 1 d . . . 
C11 C 0.0648(2) 0.1488(2) -0.11060(16) 0.0378(5) Uani 1 1 d . . . 
H11 H 0.0798 0.1328 -0.1793 0.045 Uiso 1 1 calc R . . 
N1 N 0.26926(19) 0.0391(2) -0.06858(16) 0.0436(5) Uani 1 1 d . . . 
H1A H 0.3264 0.0123 -0.0243 0.052 Uiso 1 1 calc R . . 
H1B H 0.2830 0.0251 -0.1322 0.052 Uiso 1 1 calc R . . 
N2 N 0.01660(17) 0.19498(16) 0.09225(13) 0.0273(4) Uani 1 1 d . . . 
O1 O 0.18033(15) 0.12449(18) 0.24058(11) 0.0404(4) Uani 1 1 d . . . 
O2 O 0.0000 0.4164(2) 0.2500 0.0513(7) Uani 1 2 d S . . 
H2 H 0.0569 0.4435 0.2897 0.077 Uiso 0.50 1 calc PR . . 
O3 O 0.32008(16) 0.02607(18) 0.13288(14) 0.0464(4) Uani 1 1 d . . . 
Zn1 Zn 0.0000 0.21784(3) 0.2500 0.02999(14) Uani 1 2 d S . . 
  
  
_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 
C3 C11 1.363(3) . ? 
C3 C5 1.392(3) . ? 
C3 H3 0.9300 . ? 
C5 N2 1.331(3) . ? 
C5 H5 0.9300 . ? 
C7 N2 1.347(3) . ? 
C7 C10 1.408(3) . ? 
C7 C8 1.502(3) . ? 
C8 O3 1.248(3) . ? 
C8 O1 1.267(3) . ? 
C10 N1 1.352(3) . ? 
C10 C11 1.409(3) . ? 
C11 H11 0.9300 . ? 
N1 H1A 0.8600 . ? 
N1 H1B 0.8600 . ? 
N2 Zn1 2.0937(19) . ? 
O1 Zn1 2.0397(16) . ? 
O2 Zn1 1.998(2) . ? 
O2 H2 0.8200 . ? 
Zn1 O1 2.0397(16) 2 ? 
Zn1 N2 2.0937(18) 2 ? 
  
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 
C11 C3 C5 119.2(2) . . ? 
C11 C3 H3 120.4 . . ? 
C5 C3 H3 120.4 . . ? 
N2 C5 C3 121.3(2) . . ? 
N2 C5 H5 119.3 . . ? 
C3 C5 H5 119.3 . . ? 
N2 C7 C10 121.56(18) . . ? 
N2 C7 C8 114.30(18) . . ? 
C10 C7 C8 124.15(18) . . ? 
O3 C8 O1 124.30(19) . . ? 
O3 C8 C7 118.14(19) . . ? 
O1 C8 C7 117.56(17) . . ? 
N1 C10 C7 123.2(2) . . ? 
N1 C10 C11 120.0(2) . . ? 
C7 C10 C11 116.81(19) . . ? 
C3 C11 C10 120.6(2) . . ? 
C3 C11 H11 119.7 . . ? 
C10 C11 H11 119.7 . . ? 
C10 N1 H1A 120.0 . . ? 
C10 N1 H1B 120.0 . . ? 
H1A N1 H1B 120.0 . . ? 
C5 N2 C7 120.46(18) . . ? 
C5 N2 Zn1 126.83(15) . . ? 
C7 N2 Zn1 112.71(13) . . ? 
C8 O1 Zn1 115.72(13) . . ? 
Zn1 O2 H2 109.5 . . ? 
O2 Zn1 O1 117.42(5) . 2 ? 
O2 Zn1 O1 117.42(5) . . ? 
O1 Zn1 O1 125.15(11) 2 . ? 
O2 Zn1 N2 96.31(5) . 2 ? 
O1 Zn1 N2 79.57(6) 2 2 ? 
O1 Zn1 N2 94.58(6) . 2 ? 
O2 Zn1 N2 96.31(5) . . ? 
O1 Zn1 N2 94.58(6) 2 . ? 
O1 Zn1 N2 79.57(6) . . ? 
N2 Zn1 N2 167.38(9) 2 . ? 
  
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 
C11 C3 C5 N2 1.0(4) . . . . ? 
N2 C7 C8 O3 177.84(19) . . . . ? 
C10 C7 C8 O3 -2.4(3) . . . . ? 
N2 C7 C8 O1 -2.1(3) . . . . ? 
C10 C7 C8 O1 177.64(19) . . . . ? 
N2 C7 C10 N1 179.63(19) . . . . ? 
C8 C7 C10 N1 -0.1(3) . . . . ? 
N2 C7 C10 C11 0.4(3) . . . . ? 
C8 C7 C10 C11 -179.37(19) . . . . ? 
C5 C3 C11 C10 -1.3(4) . . . . ? 
N1 C10 C11 C3 -178.7(2) . . . . ? 
C7 C10 C11 C3 0.6(3) . . . . ? 
C3 C5 N2 C7 -0.1(3) . . . . ? 
C3 C5 N2 Zn1 179.82(16) . . . . ? 
C10 C7 N2 C5 -0.6(3) . . . . ? 
C8 C7 N2 C5 179.14(18) . . . . ? 
C10 C7 N2 Zn1 179.45(14) . . . . ? 
C8 C7 N2 Zn1 -0.8(2) . . . . ? 
O3 C8 O1 Zn1 -175.95(17) . . . . ? 
C7 C8 O1 Zn1 4.0(2) . . . . ? 
C8 O1 Zn1 O2 -95.13(16) . . . . ? 
C8 O1 Zn1 O1 84.87(16) . . . 2 ? 
C8 O1 Zn1 N2 165.33(16) . . . 2 ? 
C8 O1 Zn1 N2 -3.39(16) . . . . ? 
C5 N2 Zn1 O2 -61.01(18) . . . . ? 
C7 N2 Zn1 O2 118.91(13) . . . . ? 
C5 N2 Zn1 O1 57.26(19) . . . 2 ? 
C7 N2 Zn1 O1 -122.82(14) . . . 2 ? 
C5 N2 Zn1 O1 -177.81(19) . . . . ? 
C7 N2 Zn1 O1 2.11(13) . . . . ? 
C5 N2 Zn1 N2 118.99(18) . . . 2 ? 
C7 N2 Zn1 N2 -61.09(13) . . . 2 ? 
  
_diffrn_measured_fraction_theta_max    0.994 
_diffrn_reflns_theta_full              27.53 
_diffrn_measured_fraction_theta_full   0.994 
_refine_diff_density_max    0.339 
_refine_diff_density_min   -0.282 
_refine_diff_density_rms    0.073 
