# 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_ic15560-new

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            'compound 1'
_chemical_melting_point          ?
_chemical_formula_moiety         'Zn (O2 N3 C13 H8)2, 2 (C H4 O), 6 (2H O)'
_chemical_formula_sum            'C28 H36 N6 O12 Zn'
_chemical_formula_weight         714.01

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           Triclinic
_symmetry_space_group_name_H-M   P-1

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

_cell_length_a                   12.4693(7)
_cell_length_b                   13.2851(7)
_cell_length_c                   13.1755(7)
_cell_angle_alpha                112.3007(11)
_cell_angle_beta                 105.3967(12)
_cell_angle_gamma                97.7284(12)
_cell_volume                     1877.96(18)
_cell_formula_units_Z            2
_cell_measurement_temperature    150(2)
_cell_measurement_reflns_used    4516
_cell_measurement_theta_min      2.45
_cell_measurement_theta_max      26.50

_exptl_crystal_description       plate
_exptl_crystal_colour            colorless
_exptl_crystal_size_max          0.38
_exptl_crystal_size_mid          0.25
_exptl_crystal_size_min          0.11
_exptl_crystal_density_meas      not_measured
_exptl_crystal_density_diffrn    1.260
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             740
_exptl_absorpt_coefficient_mu    0.718
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.7721
_exptl_absorpt_correction_T_max  0.9252
_exptl_absorpt_process_details   'SADABS (Bruker, 2001)'

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      150(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 APEXCCD area detector'
_diffrn_measurement_method       'omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            24255
_diffrn_reflns_av_R_equivalents  0.0490
_diffrn_reflns_av_sigmaI/netI    0.0613
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_theta_min         1.78
_diffrn_reflns_theta_max         27.50
_reflns_number_total             8587
_reflns_number_gt                7105
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'Bruker SMART'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_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)+(0.1415P)²+4.2300P] 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         8587
_refine_ls_number_parameters     420
_refine_ls_number_restraints     9
_refine_ls_R_factor_all          0.1023
_refine_ls_R_factor_gt           0.0870
_refine_ls_wR_factor_ref         0.2544
_refine_ls_wR_factor_gt          0.2423
_refine_ls_goodness_of_fit_ref   1.104
_refine_ls_restrained_S_all      1.241
_refine_ls_shift/su_max          0.002
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
Zn Zn 0.21873(5) 0.47953(4) 0.49144(5) 0.0206(2) Uani 1 1 d . . .
O1 O 0.1371(3) -0.4300(3) 0.4262(3) 0.0263(8) Uani 1 1 d . . .
O2 O 0.2960(3) -0.2899(3) 0.5042(4) 0.0326(9) Uani 1 1 d . . .
O3 O 0.2555(4) 0.5506(3) 0.6604(3) 0.0284(8) Uani 1 1 d . . .
O4 O 0.3079(3) 0.3906(3) 0.6316(3) 0.0270(8) Uani 1 1 d . . .
N1 N 0.0822(4) 0.3368(3) 0.4098(4) 0.0234(9) Uani 1 1 d . . .
N2 N 0.1183(4) 0.0170(4) 0.4075(4) 0.0263(10) Uani 1 1 d . . .
H2 H 0.1861 0.0662 0.4380 0.032 Uiso 1 1 calc R . .
N3 N -0.0695(4) -0.0530(4) 0.3264(4) 0.0268(10) Uani 1 1 d . . .
N4 N 0.3334(4) 0.4370(4) 1.4094(4) 0.0229(9) Uani 1 1 d . . .
N5 N 0.3836(4) 0.4024(4) 1.0493(4) 0.0230(9) Uani 1 1 d . . .
H5 H 0.3953 0.3346 1.0267 0.028 Uiso 1 1 calc R . .
N6 N 0.3673(5) 0.5689(4) 1.1672(4) 0.0350(11) Uani 1 1 d . . .
C1 C -0.0235(5) 0.3412(4) 0.3561(5) 0.0288(11) Uani 1 1 d . . .
H1 H -0.0337 0.4109 0.3564 0.035 Uiso 1 1 calc R . .
C2 C -0.1177(5) 0.2491(5) 0.3006(6) 0.0350(13) Uani 1 1 d . . .
H2A H -0.1915 0.2557 0.2642 0.042 Uiso 1 1 calc R . .
C3 C -0.1042(5) 0.1469(5) 0.2984(6) 0.0345(13) Uani 1 1 d . . .
H3 H -0.1677 0.0817 0.2584 0.041 Uiso 1 1 calc R . .
C4 C 0.0041(5) 0.1412(4) 0.3556(5) 0.0243(10) Uani 1 1 d . . .
C5 C 0.0947(4) 0.2363(4) 0.4086(4) 0.0216(10) Uani 1 1 d . . .
H5A H 0.1691 0.2317 0.4459 0.026 Uiso 1 1 calc R . .
C6 C 0.0191(4) 0.0352(4) 0.3619(5) 0.0224(10) Uani 1 1 d . . .
C7 C 0.0996(4) -0.0898(4) 0.4001(5) 0.0209(10) Uani 1 1 d . . .
C8 C 0.1710(4) -0.1521(4) 0.4336(5) 0.0246(11) Uani 1 1 d . . .
H8 H 0.2523 -0.1220 0.4686 0.030 Uiso 1 1 calc R . .
C9 C 0.1181(4) -0.2606(4) 0.4135(4) 0.0200(9) Uani 1 1 d . . .
C10 C -0.0024(5) -0.3041(4) 0.3613(5) 0.0262(11) Uani 1 1 d . . .
H10 H -0.0362 -0.3788 0.3472 0.031 Uiso 1 1 calc R . .
C11 C -0.0731(5) -0.2411(5) 0.3300(6) 0.0310(12) Uani 1 1 d . . .
H11 H -0.1545 -0.2706 0.2965 0.037 Uiso 1 1 calc R . .
C12 C -0.0203(4) -0.1328(4) 0.3494(5) 0.0235(10) Uani 1 1 d . . .
C13 C 0.1900(5) -0.3297(4) 0.4513(4) 0.0235(10) Uani 1 1 d . . .
C14 C 0.3968(5) 0.3650(4) 1.4225(5) 0.0258(11) Uani 1 1 d . . .
H14 H 0.3971 0.3409 1.4819 0.031 Uiso 1 1 calc R . .
C15 C 0.4610(5) 0.3254(5) 1.3527(5) 0.0297(12) Uani 1 1 d . . .
H15 H 0.5061 0.2762 1.3653 0.036 Uiso 1 1 calc R . .
C16 C 0.4595(5) 0.3577(5) 1.2640(5) 0.0275(11) Uani 1 1 d . . .
H16 H 0.5020 0.3297 1.2141 0.033 Uiso 1 1 calc R . .
C17 C 0.3949(5) 0.4316(4) 1.2494(5) 0.0256(11) Uani 1 1 d . . .
C18 C 0.3334(5) 0.4693(4) 1.3248(5) 0.0260(11) Uani 1 1 d . . .
H18 H 0.2895 0.5204 1.3155 0.031 Uiso 1 1 calc R . .
C19 C 0.3837(5) 0.4695(4) 1.1566(5) 0.0261(11) Uani 1 1 d . . .
C20 C 0.3614(4) 0.4610(4) 0.9820(4) 0.0220(10) Uani 1 1 d . . .
C21 C 0.3469(4) 0.4322(4) 0.8663(4) 0.0219(10) Uani 1 1 d . . .
H21 H 0.3563 0.3625 0.8175 0.026 Uiso 1 1 calc R . .
C22 C 0.3177(5) 0.5107(4) 0.8241(5) 0.0244(10) Uani 1 1 d . . .
C23 C 0.3116(6) 0.6171(5) 0.9003(5) 0.0354(13) Uani 1 1 d . . .
H23 H 0.2953 0.6703 0.8704 0.042 Uiso 1 1 calc R . .
C24 C 0.3286(7) 0.6456(5) 1.0162(5) 0.0419(16) Uani 1 1 d . . .
H24 H 0.3244 0.7174 1.0664 0.050 Uiso 1 1 calc R . .
C25 C 0.3526(6) 0.5654(5) 1.0588(5) 0.0318(12) Uani 1 1 d . . .
C26 C 0.2933(4) 0.4813(4) 0.6985(5) 0.0237(10) Uani 1 1 d . . .
O5 O 0.3098(4) 0.0921(4) 0.7283(4) 0.0463(11) Uani 1 1 d . . .
H5B H 0.2381 0.0887 0.7119 0.069 Uiso 1 1 d R . .
H5C H 0.3377 0.1220 0.6901 0.069 Uiso 1 1 d R . .
O6 O 0.3926(6) 0.1832(5) 0.9739(5) 0.0656(16) Uani 1 1 d . . .
H6A H 0.4655 0.1949 0.9793 0.098 Uiso 1 1 d R . .
H6B H 0.3534 0.1549 0.8992 0.098 Uiso 1 1 d R . .
O7 O 0.5730(7) 0.1181(6) 1.0804(7) 0.093(2) Uani 1 1 d . . .
H7A H 0.5795 0.0960 1.1339 0.139 Uiso 1 1 d R . .
H7B H 0.6382 0.1241 1.0716 0.139 Uiso 1 1 d R . .
O8 O 0.6033(5) 0.0951(5) 1.2871(6) 0.081(2) Uani 1 1 d . . .
H8A H 0.6150 0.1367 1.3586 0.122 Uiso 1 1 d R . .
H8B H 0.6265 0.0361 1.2799 0.122 Uiso 1 1 d R . .
O9 O 0.4240(5) -0.2339(5) 0.3736(6) 0.0756(19) Uani 1 1 d . . .
H9A H 0.4163 -0.2941 0.3138 0.113 Uiso 1 1 d R . .
H9B H 0.3789 -0.2543 0.4052 0.113 Uiso 1 1 d RD . .
O10 O 0.3910(17) -0.0432(17) 0.2965(18) 0.144(5) Uiso 0.599(9) 1 d P A 1
O11 O 0.742(2) 0.101(2) 0.963(2) 0.204(9) Uiso 0.599(9) 1 d P A 1
O12 O 0.6602(8) -0.1755(7) 0.4164(8) 0.115(3) Uani 1 1 d D . .
H12 H 0.6378 -0.2434 0.4028 0.172 Uiso 1 1 d RD . .
C27 C 0.6384(7) -0.1404(7) 0.5359(9) 0.115(3) Uani 1 1 d D . .
H27A H 0.6500 -0.0585 0.5728 0.172 Uiso 1 1 d RD . .
H27B H 0.6871 -0.1630 0.5906 0.172 Uiso 1 1 d RD . .
H27C H 0.5573 -0.1780 0.5150 0.172 Uiso 1 1 d RD . .
O13 O 1.048(4) -0.291(4) 0.986(4) 0.333(18) Uiso 0.599(9) 1 d PD A 1
C28 C 0.932(4) -0.342(5) 0.909(5) 0.25(2) Uiso 0.599(9) 1 d PD A 1
O13' O 0.988(6) -0.474(6) 0.931(6) 0.333(18) Uiso 0.401(9) 1 d PD A 2
C28' C 1.008(8) -0.416(8) 0.866(7) 0.25(2) Uiso 0.401(9) 1 d PD A 2


_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
Zn O3 1.951(4) . ?
Zn O1 1.967(3) 1_565 ?
Zn N4 2.026(4) 1_554 ?
Zn N1 2.065(4) . ?
O1 C13 1.279(6) . ?
O1 Zn 1.966(3) 1_545 ?
O2 C13 1.247(7) . ?
O3 C26 1.290(6) . ?
O4 C26 1.265(6) . ?
N1 C1 1.342(7) . ?
N1 C5 1.358(6) . ?
N2 C6 1.321(6) . ?
N2 C7 1.368(6) . ?
N3 C6 1.332(7) . ?
N3 C12 1.383(6) . ?
N4 C18 1.337(6) . ?
N4 C14 1.351(6) . ?
N4 Zn 2.026(4) 1_556 ?
N5 C19 1.355(7) . ?
N5 C20 1.386(6) . ?
N6 C19 1.325(7) . ?
N6 C25 1.373(7) . ?
C1 C2 1.375(8) . ?
C2 C3 1.382(7) . ?
C3 C4 1.388(8) . ?
C4 C5 1.374(7) . ?
C4 C6 1.475(6) . ?
C7 C8 1.393(6) . ?
C7 C12 1.400(7) . ?
C8 C9 1.395(7) . ?
C9 C10 1.407(7) . ?
C9 C13 1.492(6) . ?
C10 C11 1.383(7) . ?
C11 C12 1.395(7) . ?
C14 C15 1.379(8) . ?
C15 C16 1.386(7) . ?
C16 C17 1.387(7) . ?
C17 C18 1.399(7) . ?
C17 C19 1.470(7) . ?
C20 C21 1.376(7) . ?
C20 C25 1.412(7) . ?
C21 C22 1.401(7) . ?
C22 C23 1.416(8) . ?
C22 C26 1.481(7) . ?
C23 C24 1.375(8) . ?
C24 C25 1.411(7) . ?
O12 C27 1.574(9) . ?
O13 C28 1.414(11) . ?
O13' C28' 1.406(11) . ?

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
O3 Zn O1 108.10(16) . 1_565 ?
O3 Zn N4 125.22(17) . 1_554 ?
O1 Zn N4 107.08(16) 1_565 1_554 ?
O3 Zn N1 111.99(17) . . ?
O1 Zn N1 95.86(16) 1_565 . ?
N4 Zn N1 104.58(18) 1_554 . ?
C13 O1 Zn 119.7(3) . 1_545 ?
C26 O3 Zn 106.6(3) . . ?
C1 N1 C5 117.6(4) . . ?
C1 N1 Zn 120.1(3) . . ?
C5 N1 Zn 122.3(4) . . ?
C6 N2 C7 109.7(4) . . ?
C6 N3 C12 105.0(4) . . ?
C18 N4 C14 117.9(5) . . ?
C18 N4 Zn 117.3(3) . 1_556 ?
C14 N4 Zn 124.1(3) . 1_556 ?
C19 N5 C20 106.7(4) . . ?
C19 N6 C25 104.5(5) . . ?
N1 C1 C2 122.7(5) . . ?
C1 C2 C3 119.4(5) . . ?
C2 C3 C4 118.7(5) . . ?
C5 C4 C3 118.8(4) . . ?
C5 C4 C6 121.4(5) . . ?
C3 C4 C6 119.8(5) . . ?
N1 C5 C4 122.7(5) . . ?
N2 C6 N3 111.7(4) . . ?
N2 C6 C4 125.6(5) . . ?
N3 C6 C4 122.7(5) . . ?
N2 C7 C8 134.1(5) . . ?
N2 C7 C12 103.9(4) . . ?
C8 C7 C12 122.0(4) . . ?
C7 C8 C9 117.1(5) . . ?
C8 C9 C10 120.8(4) . . ?
C8 C9 C13 119.4(4) . . ?
C10 C9 C13 119.8(4) . . ?
C11 C10 C9 121.9(5) . . ?
C10 C11 C12 117.5(5) . . ?
N3 C12 C11 129.5(5) . . ?
N3 C12 C7 109.7(4) . . ?
C11 C12 C7 120.8(4) . . ?
O2 C13 O1 122.9(4) . . ?
O2 C13 C9 120.7(4) . . ?
O1 C13 C9 116.4(5) . . ?
N4 C14 C15 122.2(5) . . ?
C14 C15 C16 119.7(5) . . ?
C15 C16 C17 118.8(5) . . ?
C16 C17 C18 118.1(5) . . ?
C16 C17 C19 124.0(5) . . ?
C18 C17 C19 118.0(5) . . ?
N4 C18 C17 123.3(5) . . ?
N6 C19 N5 113.6(4) . . ?
N6 C19 C17 123.9(5) . . ?
N5 C19 C17 122.4(5) . . ?
C21 C20 N5 132.0(5) . . ?
C21 C20 C25 123.4(5) . . ?
N5 C20 C25 104.6(4) . . ?
C20 C21 C22 116.8(5) . . ?
C21 C22 C23 120.6(5) . . ?
C21 C22 C26 119.3(5) . . ?
C23 C22 C26 120.1(5) . . ?
C24 C23 C22 121.8(5) . . ?
C23 C24 C25 118.2(5) . . ?
N6 C25 C24 130.5(5) . . ?
N6 C25 C20 110.5(5) . . ?
C24 C25 C20 119.0(5) . . ?
O4 C26 O3 121.8(5) . . ?
O4 C26 C22 120.7(4) . . ?
O3 C26 C22 117.5(5) . . ?

_diffrn_measured_fraction_theta_max 0.996
_diffrn_reflns_theta_full        27.50
_diffrn_measured_fraction_theta_full 0.996
_refine_diff_density_max         1.439
_refine_diff_density_min         -2.063
_refine_diff_density_rms         0.179
_database_code_depnum_ccdc_archive 'CCDC 1010281'
#######################################################################
#
#                 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_ic15465-1

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            'compound 2'
_chemical_melting_point          ?
_chemical_formula_moiety         
'Zn O4 N6 C26 H16, C6 H6, 0.5C 2H 0.5O, 15H 7.5O'
_chemical_formula_sum            'C32.50 H36 N6 O12 Zn'
_chemical_formula_weight         768.04

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           Triclinic
_symmetry_space_group_name_H-M   P-1

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

_cell_length_a                   12.5650(8)
_cell_length_b                   13.2721(9)
_cell_length_c                   13.2881(9)
_cell_angle_alpha                111.9938(14)
_cell_angle_beta                 107.5534(14)
_cell_angle_gamma                97.9667(15)
_cell_volume                     1878.1(2)
_cell_formula_units_Z            2
_cell_measurement_temperature    150(2)
_cell_measurement_reflns_used    3008
_cell_measurement_theta_min      2.43
_cell_measurement_theta_max      22.16

_exptl_crystal_description       plate
_exptl_crystal_colour            light-brown
_exptl_crystal_size_max          0.35
_exptl_crystal_size_mid          0.35
_exptl_crystal_size_min          0.14
_exptl_crystal_density_meas      not_measured
_exptl_crystal_density_diffrn    1.358
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             798
_exptl_absorpt_coefficient_mu    0.720
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.7866
_exptl_absorpt_correction_T_max  0.9059
_exptl_absorpt_process_details   'SADABS (Bruker, 2001)'

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      150(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 APEXCCD area detector'
_diffrn_measurement_method       'omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            22071
_diffrn_reflns_av_R_equivalents  0.0499
_diffrn_reflns_av_unetI/netI     0.0693
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_theta_min         1.77
_diffrn_reflns_theta_max         27.50
_reflns_number_total             8591
_reflns_number_gt                6474
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'Bruker SMART'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_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)+(0.1168P)²+3.3746P] 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         8591
_refine_ls_number_parameters     466
_refine_ls_number_restraints     60
_refine_ls_R_factor_all          0.1007
_refine_ls_R_factor_gt           0.0768
_refine_ls_wR_factor_ref         0.2267
_refine_ls_wR_factor_gt          0.2112
_refine_ls_goodness_of_fit_ref   1.059
_refine_ls_restrained_S_all      1.153
_refine_ls_shift/su_max          0.001
_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
Zn Zn 0.77785(5) 0.51842(4) 0.51027(5) 0.02649(19) Uani 1 1 d . . .
O1 O 0.8618(3) 1.4283(3) 0.5741(3) 0.0329(8) Uani 1 1 d . . .
O2 O 0.7000(3) 1.2886(3) 0.4993(3) 0.0377(8) Uani 1 1 d . . .
O3 O 0.7369(3) 0.4473(3) 0.3404(3) 0.0338(8) Uani 1 1 d . . .
O4 O 0.6837(3) 0.6039(3) 0.3654(3) 0.0343(8) Uani 1 1 d . . .
N1 N 0.9183(4) 0.6610(3) 0.5884(4) 0.0319(9) Uani 1 1 d . . .
N2 N 0.8789(4) 0.9810(3) 0.5928(4) 0.0361(10) Uani 1 1 d . . .
H2 H 0.8098 0.9331 0.5658 0.043 Uiso 1 1 calc R . .
N3 N 1.0716(4) 1.0505(3) 0.6692(4) 0.0340(10) Uani 1 1 d . . .
N4 N 0.6705(4) 0.5644(3) -0.4049(4) 0.0291(9) Uani 1 1 d . . .
N5 N 0.6214(4) 0.5974(3) -0.0486(4) 0.0290(9) Uani 1 1 d D . .
H5 H 0.6074 0.6638 -0.0276 0.035 Uiso 1 1 calc R . .
N6 N 0.6436(5) 0.4360(4) -0.1611(4) 0.0462(12) Uani 1 1 d . . .
C1 C 1.0271(5) 0.6555(4) 0.6361(5) 0.0370(12) Uani 1 1 d . . .
H1 H 1.0374 0.5849 0.6329 0.044 Uiso 1 1 calc R . .
C2 C 1.1231(5) 0.7464(5) 0.6886(5) 0.0419(13) Uani 1 1 d . . .
H2A H 1.1982 0.7392 0.7225 0.050 Uiso 1 1 calc R . .
C3 C 1.1101(5) 0.8497(4) 0.6922(5) 0.0408(13) Uani 1 1 d . . .
H3 H 1.1757 0.9144 0.7291 0.049 Uiso 1 1 calc R . .
C4 C 0.9977(5) 0.8563(4) 0.6401(5) 0.0319(11) Uani 1 1 d . . .
C5 C 0.9053(4) 0.7610(4) 0.5903(5) 0.0310(10) Uani 1 1 d . . .
H5A H 0.8291 0.7656 0.5559 0.037 Uiso 1 1 calc R . .
C6 C 0.9829(5) 0.9631(4) 0.6357(5) 0.0318(11) Uani 1 1 d . . .
C7 C 0.9012(4) 1.0883(4) 0.5995(5) 0.0296(10) Uani 1 1 d . . .
C8 C 0.8281(5) 1.1502(4) 0.5665(5) 0.0323(11) Uani 1 1 d . . .
H8 H 0.7458 1.1198 0.5320 0.039 Uiso 1 1 calc R . .
C9 C 0.8816(4) 1.2583(4) 0.5866(4) 0.0270(10) Uani 1 1 d . . .
C10 C 1.0035(5) 1.3019(4) 0.6360(5) 0.0349(11) Uani 1 1 d . . .
H10 H 1.0375 1.3766 0.6492 0.042 Uiso 1 1 calc R . .
C11 C 1.0747(5) 1.2393(4) 0.6655(5) 0.0407(13) Uani 1 1 d . . .
H11 H 1.1570 1.2686 0.6973 0.049 Uiso 1 1 calc R . .
C12 C 1.0216(4) 1.1309(4) 0.6473(4) 0.0294(10) Uani 1 1 d . . .
C13 C 0.8083(5) 1.3287(4) 0.5504(4) 0.0290(10) Uani 1 1 d . . .
C14 C 0.6066(5) 0.6347(4) -0.4198(5) 0.0351(11) Uani 1 1 d . . .
H14 H 0.6029 0.6564 -0.4809 0.042 Uiso 1 1 calc R . .
C15 C 0.5461(5) 0.6764(5) -0.3502(5) 0.0417(13) Uani 1 1 d . . .
H15 H 0.5013 0.7255 -0.3639 0.050 Uiso 1 1 calc R . .
C16 C 0.5512(5) 0.6465(5) -0.2602(5) 0.0371(12) Uani 1 1 d . . .
H16 H 0.5121 0.6764 -0.2097 0.045 Uiso 1 1 calc R . .
C17 C 0.6147(5) 0.5715(4) -0.2448(4) 0.0324(11) Uani 1 1 d . . .
C18 C 0.6740(5) 0.5336(4) -0.3180(4) 0.0310(10) Uani 1 1 d . . .
H18 H 0.7189 0.4840 -0.3066 0.037 Uiso 1 1 calc R . .
C19 C 0.6264(5) 0.5343(4) -0.1519(4) 0.0329(11) Uani 1 1 d . . .
C20 C 0.6421(4) 0.5391(4) 0.0188(4) 0.0295(10) Uani 1 1 d . . .
C21 C 0.6517(4) 0.5654(4) 0.1328(4) 0.0284(10) Uani 1 1 d . . .
H21 H 0.6397 0.6336 0.1796 0.034 Uiso 1 1 calc R . .
C22 C 0.6795(4) 0.4881(4) 0.1759(4) 0.0301(10) Uani 1 1 d . . .
C23 C 0.6912(6) 0.3852(5) 0.1037(5) 0.0475(15) Uani 1 1 d . . .
H23 H 0.7085 0.3330 0.1349 0.057 Uiso 1 1 calc R . .
C24 C 0.6784(7) 0.3576(5) -0.0102(6) 0.0569(19) Uani 1 1 d . . .
H24 H 0.6844 0.2867 -0.0587 0.068 Uiso 1 1 calc R . .
C25 C 0.6559(6) 0.4379(5) -0.0528(5) 0.0409(13) Uani 1 1 d . . .
C26 C 0.7001(4) 0.5162(4) 0.3011(4) 0.0309(10) Uani 1 1 d . . .
O5 O 0.4212(4) 0.7662(4) 0.3694(5) 0.0670(14) Uani 1 1 d . . .
H5B H 0.3921 0.7642 0.4194 0.101 Uiso 1 1 d R . .
H5C H 0.4015 0.6995 0.3130 0.101 Uiso 1 1 d R . .
O6 O 0.6032(6) 0.8183(5) 0.0280(5) 0.0868(19) Uani 1 1 d D . .
H6A H 0.6440 0.8374 0.0978 0.130 Uiso 1 1 d R . .
H6B H 0.5337 0.8012 0.0183 0.130 Uiso 1 1 d R . .
O7 O 0.6879(4) 0.9104(3) 0.2708(4) 0.0465(10) Uani 1 1 d D . .
H7A H 0.6695 0.8808 0.3125 0.070 Uiso 1 1 d R . .
H7B H 0.7625 0.9347 0.2965 0.070 Uiso 1 1 d R . .
O8 O 0.6545(4) 0.8142(4) 0.4214(5) 0.0672(14) Uani 1 1 d D . .
H8A H 0.5795 0.8020 0.3866 0.101 Uiso 1 1 d R . .
H8B H 0.6650 0.7467 0.4078 0.101 Uiso 1 1 d R . .
O9 O 0.4168(6) 0.9173(5) 0.7038(5) 0.091(2) Uani 1 1 d . . .
H9A H 0.3874 0.8585 0.6352 0.137 Uiso 1 1 d R . .
H9B H 0.3794 0.9048 0.7448 0.137 Uiso 1 1 d R . .
O10 O 0.6233(11) 1.0421(10) 0.6854(14) 0.228(7) Uani 1 1 d . . .
H10A H 0.6841 1.0796 0.7382 0.342 Uiso 1 1 d R . .
H10B H 0.5731 1.0349 0.7200 0.342 Uiso 1 1 d R . .
O11 O 0.4193(9) 0.8689(8) 0.8982(9) 0.159(4) Uani 1 1 d D . .
H11A H 0.4132 0.8911 0.9611 0.239 Uiso 1 1 d RD . .
H11B H 0.4828 0.8932 0.9001 0.239 Uiso 1 1 d RD . .
O12 O 0.733(3) 1.012(3) 1.001(3) 0.269(15) Uani 0.50 1 d PU A 1
C27 C 0.624(2) 0.973(3) 0.903(3) 0.158(11) Uani 0.50 1 d PDU A 1
O13 O 0.795(2) 1.035(2) 0.846(2) 0.180(9) Uani 0.50 1 d PU B 2
C28 C 1.0016(13) 0.6730(14) 0.8911(12) 0.244(11) Uani 1 1 d GU . .
H28 H 1.0393 0.6431 0.8392 0.293 Uiso 1 1 calc R . .
C29 C 0.9529(13) 0.7602(13) 0.8883(11) 0.210(9) Uani 1 1 d GU . .
H29 H 0.9573 0.7900 0.8343 0.252 Uiso 1 1 calc R . .
C30 C 0.8978(11) 0.8040(10) 0.9643(12) 0.175(7) Uani 1 1 d GU . .
H30 H 0.8645 0.8636 0.9623 0.210 Uiso 1 1 calc R . .
C31 C 0.8913(10) 0.7604(12) 1.0432(10) 0.162(6) Uani 1 1 d GU . .
H31 H 0.8537 0.7903 1.0952 0.195 Uiso 1 1 calc R . .
C32 C 0.9401(12) 0.6732(13) 1.0461(11) 0.208(8) Uani 1 1 d GU . .
H32 H 0.9357 0.6434 1.1000 0.250 Uiso 1 1 calc R . .
C33 C 0.9952(13) 0.6295(11) 0.9701(15) 0.220(9) Uani 1 1 d GU . .
H33 H 1.0285 0.5699 0.9720 0.264 Uiso 1 1 calc R . .


_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
Zn O3 1.955(3) . ?
Zn O1 1.958(3) 1_545 ?
Zn N4 2.023(4) 1_556 ?
Zn N1 2.067(4) . ?
O1 C13 1.270(6) . ?
O1 Zn 1.958(3) 1_565 ?
O2 C13 1.252(6) . ?
O3 C26 1.285(6) . ?
O4 C26 1.247(6) . ?
N1 C1 1.348(7) . ?
N1 C5 1.351(5) . ?
N2 C6 1.352(6) . ?
N2 C7 1.376(6) . ?
N3 C6 1.318(6) . ?
N3 C12 1.388(5) . ?
N4 C14 1.343(6) . ?
N4 C18 1.352(6) . ?
N4 Zn 2.023(4) 1_554 ?
N5 C19 1.340(6) . ?
N5 C20 1.379(6) . ?
N6 C19 1.319(6) . ?
N6 C25 1.390(7) . ?
C1 C2 1.363(8) . ?
C2 C3 1.388(7) . ?
C3 C4 1.405(7) . ?
C4 C5 1.374(7) . ?
C4 C6 1.475(6) . ?
C7 C12 1.387(7) . ?
C7 C8 1.396(6) . ?
C8 C9 1.385(6) . ?
C9 C10 1.405(7) . ?
C9 C13 1.503(6) . ?
C10 C11 1.372(7) . ?
C11 C12 1.396(7) . ?
C14 C15 1.377(7) . ?
C15 C16 1.382(7) . ?
C16 C17 1.394(7) . ?
C17 C18 1.388(7) . ?
C17 C19 1.468(6) . ?
C20 C21 1.384(7) . ?
C20 C25 1.395(7) . ?
C21 C22 1.386(6) . ?
C22 C23 1.402(7) . ?
C22 C26 1.491(7) . ?
C23 C24 1.369(8) . ?
C24 C25 1.405(7) . ?
O12 C27 1.43(4) . ?
C28 C29 1.3900 . ?
C28 C33 1.3900 . ?
C29 C30 1.3900 . ?
C30 C31 1.3900 . ?
C31 C32 1.3900 . ?
C32 C33 1.3900 . ?

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
O3 Zn O1 107.30(14) . 1_545 ?
O3 Zn N4 127.18(16) . 1_556 ?
O1 Zn N4 107.79(15) 1_545 1_556 ?
O3 Zn N1 109.42(16) . . ?
O1 Zn N1 96.01(15) 1_545 . ?
N4 Zn N1 104.74(16) 1_556 . ?
C13 O1 Zn 119.9(3) . 1_565 ?
C26 O3 Zn 107.4(3) . . ?
C1 N1 C5 117.9(4) . . ?
C1 N1 Zn 120.3(3) . . ?
C5 N1 Zn 121.8(4) . . ?
C6 N2 C7 107.1(4) . . ?
C6 N3 C12 105.0(4) . . ?
C14 N4 C18 117.8(4) . . ?
C14 N4 Zn 123.9(3) . 1_554 ?
C18 N4 Zn 117.8(3) . 1_554 ?
C19 N5 C20 107.4(4) . . ?
C19 N6 C25 104.8(4) . . ?
N1 C1 C2 123.0(4) . . ?
C1 C2 C3 119.4(5) . . ?
C2 C3 C4 118.4(5) . . ?
C5 C4 C3 118.6(4) . . ?
C5 C4 C6 122.1(5) . . ?
C3 C4 C6 119.3(5) . . ?
N1 C5 C4 122.7(5) . . ?
N3 C6 N2 112.7(4) . . ?
N3 C6 C4 122.8(5) . . ?
N2 C6 C4 124.4(4) . . ?
N2 C7 C12 105.6(4) . . ?
N2 C7 C8 132.2(5) . . ?
C12 C7 C8 122.1(4) . . ?
C9 C8 C7 116.6(5) . . ?
C8 C9 C10 121.2(4) . . ?
C8 C9 C13 119.5(4) . . ?
C10 C9 C13 119.2(4) . . ?
C11 C10 C9 121.6(4) . . ?
C10 C11 C12 117.6(5) . . ?
C7 C12 N3 109.6(4) . . ?
C7 C12 C11 120.8(4) . . ?
N3 C12 C11 129.7(5) . . ?
O2 C13 O1 123.0(4) . . ?
O2 C13 C9 120.2(4) . . ?
O1 C13 C9 116.7(4) . . ?
N4 C14 C15 122.8(4) . . ?
C14 C15 C16 119.4(5) . . ?
C15 C16 C17 118.8(5) . . ?
C18 C17 C16 118.3(4) . . ?
C18 C17 C19 118.3(4) . . ?
C16 C17 C19 123.4(5) . . ?
N4 C18 C17 122.8(4) . . ?
N6 C19 N5 113.1(4) . . ?
N6 C19 C17 123.6(5) . . ?
N5 C19 C17 123.3(4) . . ?
N5 C20 C21 132.5(4) . . ?
N5 C20 C25 105.2(4) . . ?
C21 C20 C25 122.3(4) . . ?
C20 C21 C22 117.3(4) . . ?
C21 C22 C23 120.6(4) . . ?
C21 C22 C26 119.6(4) . . ?
C23 C22 C26 119.8(4) . . ?
C24 C23 C22 122.1(5) . . ?
C23 C24 C25 117.6(5) . . ?
N6 C25 C20 109.4(4) . . ?
N6 C25 C24 130.7(5) . . ?
C20 C25 C24 119.9(5) . . ?
O4 C26 O3 121.5(4) . . ?
O4 C26 C22 121.2(4) . . ?
O3 C26 C22 117.4(4) . . ?
C29 C28 C33 120.0 . . ?
C30 C29 C28 120.0 . . ?
C29 C30 C31 120.0 . . ?
C32 C31 C30 120.0 . . ?
C31 C32 C33 120.0 . . ?
C32 C33 C28 120.0 . . ?

_diffrn_measured_fraction_theta_max 0.996
_diffrn_reflns_theta_full        27.50
_diffrn_measured_fraction_theta_full 0.996
_refine_diff_density_max         0.879
_refine_diff_density_min         -0.690
_refine_diff_density_rms         0.119
_database_code_depnum_ccdc_archive 'CCDC 1010282'
#######################################################################
#
#                 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_ic15466

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            'compound 3'
_chemical_melting_point          ?
_chemical_formula_moiety         
'Zn O4 N6 C26 H16, 3.5C 4H, 0.5C 2H 0.5O, 13H 6.5O'
_chemical_formula_sum            'C60 H70 N12 O22 Zn2'
_chemical_formula_weight         1442.02

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           Triclinic
_symmetry_space_group_name_H-M   P-1

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

_cell_length_a                   12.4881(8)
_cell_length_b                   13.2558(8)
_cell_length_c                   13.2738(8)
_cell_angle_alpha                112.0191(15)
_cell_angle_beta                 107.4532(15)
_cell_angle_gamma                98.2194(16)
_cell_volume                     1860.5(2)
_cell_formula_units_Z            1
_cell_measurement_temperature    150(2)
_cell_measurement_reflns_used    3252
_cell_measurement_theta_min      2.44
_cell_measurement_theta_max      22.22

_exptl_crystal_description       plate
_exptl_crystal_colour            light-brown
_exptl_crystal_size_max          0.40
_exptl_crystal_size_mid          0.25
_exptl_crystal_size_min          0.10
_exptl_crystal_density_meas      not_measured
_exptl_crystal_density_diffrn    1.287
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             750
_exptl_absorpt_coefficient_mu    0.720
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.7615
_exptl_absorpt_correction_T_max  0.9314
_exptl_absorpt_process_details   'SADABS (Bruker, 2001)'

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      150(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 APEXCCD area detector'
_diffrn_measurement_method       'omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            24382
_diffrn_reflns_av_R_equivalents  0.0536
_diffrn_reflns_av_unetI/netI     0.0655
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_theta_min         1.79
_diffrn_reflns_theta_max         27.50
_reflns_number_total             8536
_reflns_number_gt                6662
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'Bruker SMART'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_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)+(0.1046P)²+3.1540P] 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         8536
_refine_ls_number_parameters     473
_refine_ls_number_restraints     65
_refine_ls_R_factor_all          0.0908
_refine_ls_R_factor_gt           0.0710
_refine_ls_wR_factor_ref         0.2117
_refine_ls_wR_factor_gt          0.1987
_refine_ls_goodness_of_fit_ref   1.099
_refine_ls_restrained_S_all      1.098
_refine_ls_shift/su_max          0.002
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
Zn Zn 0.22238(4) 0.48353(4) 0.49142(4) 0.02167(16) Uani 1 1 d . . .
O1 O 0.1374(3) -0.4273(2) 0.4270(3) 0.0276(6) Uani 1 1 d . . .
O2 O 0.3010(3) -0.2868(2) 0.5026(3) 0.0319(7) Uani 1 1 d . . .
O3 O 0.2630(3) 0.5550(2) 0.6611(3) 0.0283(6) Uani 1 1 d . . .
O4 O 0.3178(3) 0.3990(2) 0.6364(3) 0.0283(6) Uani 1 1 d . . .
N1 N 0.0816(3) 0.3397(3) 0.4126(3) 0.0262(7) Uani 1 1 d . . .
N2 N 0.1227(3) 0.0219(3) 0.4113(3) 0.0289(8) Uani 1 1 d . . .
H2 H 0.1920 0.0716 0.4412 0.035 Uiso 1 1 calc R . .
N3 N -0.0717(3) -0.0512(3) 0.3285(3) 0.0321(8) Uani 1 1 d . . .
N4 N 0.3295(3) 0.4366(3) 1.4057(3) 0.0239(7) Uani 1 1 d . . .
N5 N 0.3774(3) 0.4025(3) 1.0477(3) 0.0235(7) Uani 1 1 d . . .
H5 H 0.3917 0.3361 1.0265 0.028 Uiso 1 1 calc R . .
N6 N 0.3511(4) 0.5631(3) 1.1604(3) 0.0400(10) Uani 1 1 d . . .
C1 C -0.0274(4) 0.3438(4) 0.3622(4) 0.0315(10) Uani 1 1 d . . .
H1 H -0.0376 0.4140 0.3642 0.038 Uiso 1 1 calc R . .
C2 C -0.1240(4) 0.2519(4) 0.3085(5) 0.0366(11) Uani 1 1 d . . .
H2A H -0.1995 0.2582 0.2729 0.044 Uiso 1 1 calc R . .
C3 C -0.1104(4) 0.1494(4) 0.3065(4) 0.0327(10) Uani 1 1 d . . .
H3 H -0.1764 0.0842 0.2696 0.039 Uiso 1 1 calc R . .
C4 C 0.0017(4) 0.1432(3) 0.3594(4) 0.0273(9) Uani 1 1 d . . .
C5 C 0.0951(4) 0.2398(3) 0.4106(4) 0.0267(9) Uani 1 1 d . . .
H5A H 0.1718 0.2358 0.4459 0.032 Uiso 1 1 calc R . .
C6 C 0.0172(4) 0.0372(3) 0.3647(4) 0.0263(9) Uani 1 1 d . . .
C7 C 0.1003(4) -0.0867(3) 0.4025(4) 0.0253(9) Uani 1 1 d . . .
C8 C 0.1726(4) -0.1481(3) 0.4359(4) 0.0263(9) Uani 1 1 d . . .
H8 H 0.2554 -0.1166 0.4723 0.032 Uiso 1 1 calc R . .
C9 C 0.1191(4) -0.2578(3) 0.4142(4) 0.0235(8) Uani 1 1 d . . .
C10 C -0.0028(4) -0.3026(3) 0.3612(4) 0.0327(10) Uani 1 1 d . . .
H10 H -0.0368 -0.3783 0.3459 0.039 Uiso 1 1 calc R . .
C11 C -0.0752(4) -0.2412(4) 0.3304(5) 0.0380(11) Uani 1 1 d . . .
H11 H -0.1581 -0.2722 0.2965 0.046 Uiso 1 1 calc R . .
C12 C -0.0218(4) -0.1309(3) 0.3512(4) 0.0275(9) Uani 1 1 d . . .
C13 C 0.1924(4) -0.3273(3) 0.4512(4) 0.0234(8) Uani 1 1 d . . .
C14 C 0.3925(4) 0.3657(4) 1.4197(4) 0.0284(9) Uani 1 1 d . . .
H14 H 0.3971 0.3446 1.4815 0.034 Uiso 1 1 calc R . .
C15 C 0.4509(4) 0.3222(4) 1.3482(4) 0.0340(10) Uani 1 1 d . . .
H15 H 0.4942 0.2716 1.3604 0.041 Uiso 1 1 calc R . .
C16 C 0.4461(4) 0.3527(4) 1.2586(4) 0.0301(9) Uani 1 1 d . . .
H16 H 0.4851 0.3226 1.2077 0.036 Uiso 1 1 calc R . .
C17 C 0.3831(4) 0.4285(3) 1.2442(4) 0.0258(8) Uani 1 1 d . . .
C18 C 0.3254(4) 0.4675(3) 1.3194(4) 0.0246(8) Uani 1 1 d . . .
H18 H 0.2812 0.5182 1.3093 0.030 Uiso 1 1 calc R . .
C19 C 0.3717(4) 0.4662(3) 1.1516(4) 0.0262(8) Uani 1 1 d . . .
C20 C 0.3566(4) 0.4618(3) 0.9815(4) 0.0248(8) Uani 1 1 d . . .
C21 C 0.3488(3) 0.4368(3) 0.8685(3) 0.0229(8) Uani 1 1 d . . .
H21 H 0.3630 0.3696 0.8222 0.027 Uiso 1 1 calc R . .
C22 C 0.3195(4) 0.5135(3) 0.8252(4) 0.0249(8) Uani 1 1 d . . .
C23 C 0.3040(5) 0.6154(4) 0.8965(4) 0.0428(12) Uani 1 1 d . . .
H23 H 0.2853 0.6674 0.8654 0.051 Uiso 1 1 calc R . .
C24 C 0.3154(6) 0.6411(4) 1.0104(5) 0.0532(16) Uani 1 1 d . . .
H24 H 0.3063 0.7106 1.0585 0.064 Uiso 1 1 calc R . .
C25 C 0.3406(5) 0.5625(4) 1.0533(4) 0.0361(11) Uani 1 1 d . . .
C26 C 0.3008(4) 0.4870(3) 0.7011(4) 0.0249(8) Uani 1 1 d . . .
O5 O 0.5782(4) 0.2329(3) 0.6290(4) 0.0549(10) Uani 1 1 d . . .
H5B H 0.6060 0.2945 0.6943 0.082 Uiso 1 1 d R . .
H5C H 0.6147 0.2399 0.5859 0.082 Uiso 1 1 d R . .
O6 O 0.3966(6) 0.1858(4) 0.9719(4) 0.0871(17) Uani 1 1 d . . .
H6A H 0.3576 0.1569 0.9005 0.131 Uiso 1 1 d R . .
H6B H 0.4702 0.1953 0.9889 0.131 Uiso 1 1 d R . .
O7 O 0.3133(3) 0.0918(3) 0.7282(3) 0.0402(8) Uani 1 1 d . . .
H7B H 0.2385 0.0758 0.7039 0.060 Uiso 1 1 d R . .
H7A H 0.3370 0.1281 0.6936 0.060 Uiso 1 1 d R . .
O8 O 0.3454(3) 0.1873(3) 0.5815(3) 0.0484(9) Uani 1 1 d . . .
H8A H 0.3289 0.2480 0.5940 0.073 Uiso 1 1 d R . .
H8B H 0.4218 0.2006 0.6115 0.073 Uiso 1 1 d R . .
O9 O 0.5823(4) 1.0833(4) 0.2920(4) 0.0813(16) Uani 1 1 d . . .
H9A H 0.6233 1.0375 0.2962 0.122 Uiso 1 1 d R . .
H9B H 0.6080 1.1428 0.3584 0.122 Uiso 1 1 d R . .
O10 O 0.5635(6) 1.1173(6) 0.0920(7) 0.119(2) Uani 1 1 d . . .
H10A H 0.6042 1.0795 0.1221 0.178 Uiso 1 1 d R . .
H10B H 0.5091 1.1214 0.1221 0.178 Uiso 1 1 d R . .
O11 O 0.3749(14) 0.9542(14) 0.308(2) 0.172(6) Uani 0.50 1 d P A -1
O12 O 0.2235(15) 0.9112(14) 0.159(2) 0.172(6) Uani 0.50 1 d PD B 2
H12 H 0.2844 0.9023 0.1992 0.258 Uiso 0.50 1 d PR B 2
C27 C 0.241(3) 0.954(3) 0.078(3) 0.25(2) Uani 0.50 1 d PD B 2
H27A H 0.1727 0.9785 0.0472 0.376 Uiso 0.50 1 calc PR B 2
H27B H 0.2500 0.8946 0.0132 0.376 Uiso 0.50 1 calc PR B 2
H27C H 0.3114 1.0195 0.1198 0.376 Uiso 0.50 1 calc PR B 2
C28 C 0.9621(18) 0.6141(18) 0.9574(17) 0.121(6) Uani 0.50 1 d PDU C -1
C29 C 0.9220(15) 0.6791(18) 1.0383(18) 0.119(6) Uani 0.50 1 d PDU C -1
H29A H 0.9167 0.6566 1.0971 0.142 Uiso 0.50 1 calc PR C -1
C30 C 0.8892(18) 0.7741(17) 1.0399(14) 0.115(6) Uani 0.50 1 d PDU C -1
H30A H 0.8568 0.8136 1.0937 0.138 Uiso 0.50 1 calc PR C -1
C31 C 0.9055(14) 0.8074(17) 0.9617(14) 0.114(5) Uani 0.50 1 d PDU C -1
H31A H 0.8878 0.8744 0.9605 0.137 Uiso 0.50 1 calc PR C -1
C32 C 0.9475(18) 0.7452(19) 0.8834(17) 0.123(6) Uani 0.50 1 d PDU C -1
H32A H 0.9531 0.7698 0.8261 0.148 Uiso 0.50 1 calc PR C -1
C33 C 0.984(2) 0.648(2) 0.8781(17) 0.128(6) Uani 0.50 1 d PDU C -1
H33A H 1.0188 0.6106 0.8260 0.154 Uiso 0.50 1 calc PR C -1
C34 C 0.995(3) 0.508(2) 0.950(2) 0.144(8) Uani 0.50 1 d PDU C -1
H34A H 1.0541 0.4993 0.9159 0.216 Uiso 0.50 1 calc PR C -1
H34B H 0.9250 0.4419 0.9009 0.216 Uiso 0.50 1 calc PR C -1
H34C H 1.0263 0.5125 1.0295 0.216 Uiso 0.50 1 calc PR C -1


_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
Zn O3 1.950(3) . ?
Zn O1 1.957(3) 1_565 ?
Zn N4 2.022(3) 1_554 ?
Zn N1 2.064(4) . ?
O1 C13 1.273(5) . ?
O1 Zn 1.957(3) 1_545 ?
O2 C13 1.247(5) . ?
O3 C26 1.283(5) . ?
O4 C26 1.255(5) . ?
N1 C1 1.343(5) . ?
N1 C5 1.350(5) . ?
N2 C6 1.357(5) . ?
N2 C7 1.380(5) . ?
N3 C6 1.313(5) . ?
N3 C12 1.382(5) . ?
N4 C14 1.339(5) . ?
N4 C18 1.344(5) . ?
N4 Zn 2.022(3) 1_556 ?
N5 C19 1.351(5) . ?
N5 C20 1.377(5) . ?
N6 C19 1.315(5) . ?
N6 C25 1.384(6) . ?
C1 C2 1.364(6) . ?
C2 C3 1.386(6) . ?
C3 C4 1.394(6) . ?
C4 C5 1.381(6) . ?
C4 C6 1.471(5) . ?
C7 C8 1.383(5) . ?
C7 C12 1.398(6) . ?
C8 C9 1.392(5) . ?
C9 C10 1.396(6) . ?
C9 C13 1.496(5) . ?
C10 C11 1.373(6) . ?
C11 C12 1.403(6) . ?
C14 C15 1.374(6) . ?
C15 C16 1.381(6) . ?
C16 C17 1.395(6) . ?
C17 C18 1.391(6) . ?
C17 C19 1.468(5) . ?
C20 C21 1.379(5) . ?
C20 C25 1.402(6) . ?
C21 C22 1.385(5) . ?
C22 C23 1.408(6) . ?
C22 C26 1.484(6) . ?
C23 C24 1.375(7) . ?
C24 C25 1.393(6) . ?
O12 C27 1.445(18) . ?
C28 C33 1.367(17) . ?
C28 C29 1.378(16) . ?
C28 C34 1.501(18) . ?
C29 C30 1.374(17) . ?
C30 C31 1.325(16) . ?
C31 C32 1.358(16) . ?
C32 C33 1.411(17) . ?

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
O3 Zn O1 107.30(12) . 1_565 ?
O3 Zn N4 127.66(13) . 1_554 ?
O1 Zn N4 107.89(13) 1_565 1_554 ?
O3 Zn N1 109.59(13) . . ?
O1 Zn N1 95.93(13) 1_565 . ?
N4 Zn N1 103.91(14) 1_554 . ?
C13 O1 Zn 119.1(3) . 1_545 ?
C26 O3 Zn 107.6(3) . . ?
C1 N1 C5 117.9(4) . . ?
C1 N1 Zn 120.2(3) . . ?
C5 N1 Zn 121.8(3) . . ?
C6 N2 C7 106.7(3) . . ?
C6 N3 C12 105.0(3) . . ?
C14 N4 C18 118.2(4) . . ?
C14 N4 Zn 123.9(3) . 1_556 ?
C18 N4 Zn 117.3(3) . 1_556 ?
C19 N5 C20 106.5(3) . . ?
C19 N6 C25 104.6(4) . . ?
N1 C1 C2 123.2(4) . . ?
C1 C2 C3 118.9(4) . . ?
C2 C3 C4 119.0(4) . . ?
C5 C4 C3 118.4(4) . . ?
C5 C4 C6 121.7(4) . . ?
C3 C4 C6 119.8(4) . . ?
N1 C5 C4 122.5(4) . . ?
N3 C6 N2 113.3(3) . . ?
N3 C6 C4 122.5(4) . . ?
N2 C6 C4 124.2(4) . . ?
N2 C7 C8 132.7(4) . . ?
N2 C7 C12 105.3(3) . . ?
C8 C7 C12 122.1(4) . . ?
C7 C8 C9 117.3(4) . . ?
C8 C9 C10 120.6(4) . . ?
C8 C9 C13 119.8(4) . . ?
C10 C9 C13 119.5(3) . . ?
C11 C10 C9 122.4(4) . . ?
C10 C11 C12 117.2(4) . . ?
N3 C12 C7 109.8(3) . . ?
N3 C12 C11 129.9(4) . . ?
C7 C12 C11 120.3(4) . . ?
O2 C13 O1 123.5(4) . . ?
O2 C13 C9 120.3(3) . . ?
O1 C13 C9 116.2(4) . . ?
N4 C14 C15 122.6(4) . . ?
C14 C15 C16 119.5(4) . . ?
C15 C16 C17 118.8(4) . . ?
C18 C17 C16 118.0(4) . . ?
C18 C17 C19 118.5(4) . . ?
C16 C17 C19 123.4(4) . . ?
N4 C18 C17 122.8(4) . . ?
N6 C19 N5 113.8(4) . . ?
N6 C19 C17 123.3(4) . . ?
N5 C19 C17 122.9(4) . . ?
N5 C20 C21 132.1(4) . . ?
N5 C20 C25 105.5(4) . . ?
C21 C20 C25 122.4(4) . . ?
C20 C21 C22 117.4(4) . . ?
C21 C22 C23 120.8(4) . . ?
C21 C22 C26 119.8(4) . . ?
C23 C22 C26 119.3(4) . . ?
C24 C23 C22 121.3(4) . . ?
C23 C24 C25 118.3(4) . . ?
N6 C25 C24 130.7(4) . . ?
N6 C25 C20 109.5(4) . . ?
C24 C25 C20 119.7(4) . . ?
O4 C26 O3 121.1(4) . . ?
O4 C26 C22 121.0(4) . . ?
O3 C26 C22 117.9(4) . . ?
C33 C28 C29 121(2) . . ?
C33 C28 C34 112.9(18) . . ?
C29 C28 C34 126(2) . . ?
C30 C29 C28 125(2) . . ?
C31 C30 C29 116(2) . . ?
C30 C31 C32 120(2) . . ?
C31 C32 C33 127(2) . . ?
C28 C33 C32 112(2) . . ?

_diffrn_measured_fraction_theta_max 0.998
_diffrn_reflns_theta_full        27.50
_diffrn_measured_fraction_theta_full 0.998
_refine_diff_density_max         1.283
_refine_diff_density_min         -0.567
_refine_diff_density_rms         0.134
_database_code_depnum_ccdc_archive 'CCDC 1010283'
