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

####################################################################### 
# 
# 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_1
_database_code_depnum_ccdc_archive 'CCDC 1448462'
_audit_update_record             
;
2016-01-19 deposited with the CCDC.
2016-02-05 downloaded from the CCDC.
;

_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
####################################################################### 
# 
# 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_2
_database_code_depnum_ccdc_archive 'CCDC 1448463'
_audit_update_record             
;
2016-01-19 deposited with the CCDC.
2016-02-05 downloaded from the CCDC.
;

_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
