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

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#
#                 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
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#  except for the purpose of generating routine backup copies
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data_1

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C7 H13 N10 O8 Zn2'
_chemical_formula_weight         496.05

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   P21/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                   12.511(3)
_cell_length_b                   10.165(2)
_cell_length_c                   12.487(3)
_cell_angle_alpha                90.00
_cell_angle_beta                 102.05(3)
_cell_angle_gamma                90.00
_cell_volume                     1553.0(6)
_cell_formula_units_Z            4
_cell_measurement_temperature    153(2)
_cell_measurement_reflns_used    10001
_cell_measurement_theta_min      3.275
_cell_measurement_theta_max      27.66

_exptl_crystal_description       BLOCK
_exptl_crystal_colour            Colorless
_exptl_crystal_size_max          0.20
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.20
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    2.122
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             996
_exptl_absorpt_coefficient_mu    3.159
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.5707
_exptl_absorpt_correction_T_max  0.5707
_exptl_absorpt_process_details   sadabs

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      153(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 P4'
_diffrn_measurement_method       'ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            11723
_diffrn_reflns_av_R_equivalents  0.1116
_diffrn_reflns_av_sigmaI/netI    0.0892
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_theta_min         3.28
_diffrn_reflns_theta_max         25.00
_reflns_number_total             2726
_reflns_number_gt                2242
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'Bruker XSCANS'
_computing_cell_refinement       'Bruker XSCANS'
_computing_data_reduction        'Bruker SHELXTL'
_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)+(0.0900P)²+10.7529P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     SHELXL
_refine_ls_extinction_coef       0.0104(16)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_number_reflns         2726
_refine_ls_number_parameters     245
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0804
_refine_ls_R_factor_gt           0.0676
_refine_ls_wR_factor_ref         0.1916
_refine_ls_wR_factor_gt          0.1816
_refine_ls_goodness_of_fit_ref   1.029
_refine_ls_restrained_S_all      1.029
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C 0.1806(6) 0.9650(8) 0.1877(7) 0.0278(17) Uani 1 1 d . . .
C2 C 0.0856(6) 0.9800(7) 0.0882(7) 0.0254(17) Uani 1 1 d . . .
C3 C 0.0745(6) 1.0990(7) 0.0335(6) 0.0264(17) Uani 1 1 d . . .
H3A H 0.1261 1.1671 0.0570 0.032 Uiso 1 1 calc R . .
C4 C 0.0117(6) 0.6206(7) 0.5559(6) 0.0230(16) Uani 1 1 d . . .
C5 C 0.0215(6) 0.7546(8) 0.6060(7) 0.0305(18) Uani 1 1 d . . .
C6 C 0.5040(6) 0.7869(7) 0.2110(6) 0.0232(16) Uani 1 1 d . . .
C7 C 0.2995(6) 0.9639(7) 0.5132(7) 0.0254(16) Uani 1 1 d . . .
N1 N 0.4837(5) 1.1579(6) 0.2696(5) 0.0254(14) Uani 1 1 d . . .
N2 N 0.4691(6) 0.6322(6) 0.3164(6) 0.0366(18) Uani 1 1 d . . .
N3 N 0.4288(6) 0.7406(6) 0.3469(6) 0.0343(17) Uani 1 1 d . . .
N4 N 0.4488(5) 0.8406(6) 0.2821(5) 0.0265(14) Uani 1 1 d . . .
N5 N 0.5352(5) 0.8539(6) 0.1294(6) 0.0310(16) Uani 1 1 d . . .
H5A H 0.5670 0.8123 0.0827 0.037 Uiso 1 1 calc R . .
H5B H 0.5238 0.9392 0.1229 0.037 Uiso 1 1 calc R . .
N6 N 0.3519(5) 1.0382(6) 0.4527(5) 0.0274(15) Uani 1 1 d . . .
N7 N 0.3402(6) 1.1643(6) 0.4877(6) 0.0306(15) Uani 1 1 d . . .
N8 N 0.2838(6) 1.1629(6) 0.5615(6) 0.0331(16) Uani 1 1 d . . .
N9 N 0.2562(6) 1.0360(6) 0.5803(6) 0.0294(15) Uani 1 1 d . . .
N10 N 0.2950(6) 0.8317(6) 0.5081(6) 0.0376(18) Uani 1 1 d . . .
H10A H 0.2612 0.7876 0.5518 0.045 Uiso 1 1 calc R . .
H10B H 0.3259 0.7894 0.4611 0.045 Uiso 1 1 calc R . .
O1 O 0.2609(4) 1.0421(6) 0.1901(5) 0.0335(13) Uani 1 1 d . . .
O2 O 0.1731(5) 0.8852(6) 0.2584(5) 0.0410(15) Uani 1 1 d . . .
O3 O 0.1028(5) 0.8218(5) 0.5961(5) 0.0380(15) Uani 1 1 d . . .
O4 O -0.0514(6) 0.7971(7) 0.6471(8) 0.083(3) Uani 1 1 d . . .
O5 O 0.1827(5) 0.8974(6) 0.8136(5) 0.0465(16) Uani 1 1 d . . .
H5C H 0.1730 0.8183 0.7985 0.070 Uiso 1 1 d R . .
H5D H 0.2355 0.9193 0.8661 0.070 Uiso 1 1 d R . .
O6 O 0.2002(5) 1.1738(6) 0.7649(5) 0.0419(15) Uani 1 1 d . . .
H6A H 0.2034 1.2233 0.8204 0.063 Uiso 1 1 d R . .
H6B H 0.2431 1.2053 0.7269 0.063 Uiso 1 1 d R . .
O7 O -0.0025(5) 1.0680(8) 0.6344(6) 0.0561(19) Uani 1 1 d . . .
H7A H -0.0576 1.0597 0.6638 0.084 Uiso 1 1 d R . .
H7B H -0.0229 1.1108 0.5752 0.084 Uiso 1 1 d R . .
O8 O 0.3280(5) 0.9781(6) -0.0121(5) 0.0448(16) Uani 1 1 d . . .
H8A H 0.3041 1.0164 0.0386 0.067 Uiso 1 1 d R . .
H8B H 0.3852 0.9312 0.0077 0.067 Uiso 1 1 d R . .
Zn1 Zn 0.39013(7) 1.01504(8) 0.30914(7) 0.0218(3) Uani 1 1 d . . .
Zn2 Zn 0.14903(8) 1.00020(8) 0.67564(8) 0.0310(4) Uani 1 1 d . . .


_geom_special_details            
; 
 All esds (except the esd in the dihedral angle between two l.s. planes) 
 are estimated using the full covariance matrix.  The cell esds are taken 
 into account individually in the estimation of esds in distances, angles 
 and torsion angles; correlations between esds in cell parameters are only 
 used when they are defined by crystal symmetry.  An approximate (isotropic) 
 treatment of cell esds is used for estimating esds involving l.s. planes. 
;

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
C1 O2 1.217(10) . ?
C1 O1 1.269(10) . ?
C1 C2 1.537(11) . ?
C2 C4 1.381(10) 4_575 ?
C2 C3 1.382(10) . ?
C3 C4 1.399(10) 2 ?
C3 H3A 0.9500 . ?
C4 C2 1.381(10) 4_576 ?
C4 C3 1.399(10) 2_545 ?
C4 C5 1.493(10) . ?
C5 O4 1.215(10) . ?
C5 O3 1.252(9) . ?
C6 N1 1.336(9) 2_645 ?
C6 N5 1.350(10) . ?
C6 N4 1.349(9) . ?
C7 N9 1.313(10) . ?
C7 N6 1.333(10) . ?
C7 N10 1.345(10) . ?
N1 C6 1.336(9) 2_655 ?
N1 N2 1.354(9) 2_655 ?
N1 Zn1 1.991(6) . ?
N2 N3 1.303(9) . ?
N2 N1 1.354(9) 2_645 ?
N3 N4 1.354(9) . ?
N4 Zn1 1.974(6) . ?
N5 H5A 0.8800 . ?
N5 H5B 0.8800 . ?
N6 N7 1.372(9) . ?
N6 Zn1 1.964(7) . ?
N7 N8 1.273(9) . ?
N8 N9 1.369(9) . ?
N9 Zn2 2.003(6) . ?
N10 H10A 0.8800 . ?
N10 H10B 0.8800 . ?
O1 Zn1 1.974(6) . ?
O3 Zn2 2.091(5) . ?
O5 Zn2 1.984(6) . ?
O5 H5C 0.8294 . ?
O5 H5D 0.8569 . ?
O6 Zn2 2.114(6) . ?
O6 H6A 0.8501 . ?
O6 H6B 0.8500 . ?
O7 Zn2 1.982(7) . ?
O7 H7A 0.8500 . ?
O7 H7B 0.8499 . ?
O8 H8A 0.8480 . ?
O8 H8B 0.8527 . ?

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
O2 C1 O1 125.1(8) . . ?
O2 C1 C2 119.3(7) . . ?
O1 C1 C2 115.6(7) . . ?
C4 C2 C3 120.8(7) 4_575 . ?
C4 C2 C1 121.3(7) 4_575 . ?
C3 C2 C1 117.9(7) . . ?
C2 C3 C4 120.9(7) . 2 ?
C2 C3 H3A 119.6 . . ?
C4 C3 H3A 119.6 2 . ?
C2 C4 C3 118.3(7) 4_576 2_545 ?
C2 C4 C5 124.2(7) 4_576 . ?
C3 C4 C5 117.4(7) 2_545 . ?
O4 C5 O3 123.0(8) . . ?
O4 C5 C4 119.9(7) . . ?
O3 C5 C4 117.0(7) . . ?
N1 C6 N5 126.3(7) 2_645 . ?
N1 C6 N4 109.5(6) 2_645 . ?
N5 C6 N4 124.1(7) . . ?
N9 C7 N6 111.3(7) . . ?
N9 C7 N10 124.7(7) . . ?
N6 C7 N10 124.0(7) . . ?
C6 N1 N2 106.3(6) 2_655 2_655 ?
C6 N1 Zn1 136.2(5) 2_655 . ?
N2 N1 Zn1 115.6(5) 2_655 . ?
N3 N2 N1 109.1(6) . 2_645 ?
N2 N3 N4 109.2(6) . . ?
C6 N4 N3 105.8(6) . . ?
C6 N4 Zn1 137.4(5) . . ?
N3 N4 Zn1 116.8(5) . . ?
C6 N5 H5A 120.0 . . ?
C6 N5 H5B 120.0 . . ?
H5A N5 H5B 120.0 . . ?
C7 N6 N7 104.6(6) . . ?
C7 N6 Zn1 133.8(6) . . ?
N7 N6 Zn1 117.7(5) . . ?
N8 N7 N6 109.4(6) . . ?
N7 N8 N9 109.4(6) . . ?
C7 N9 N8 105.3(6) . . ?
C7 N9 Zn2 134.0(5) . . ?
N8 N9 Zn2 119.8(5) . . ?
C7 N10 H10A 120.0 . . ?
C7 N10 H10B 120.0 . . ?
H10A N10 H10B 120.0 . . ?
C1 O1 Zn1 116.8(5) . . ?
C5 O3 Zn2 125.2(5) . . ?
Zn2 O5 H5C 108.6 . . ?
Zn2 O5 H5D 121.2 . . ?
H5C O5 H5D 118.6 . . ?
Zn2 O6 H6A 151.8 . . ?
Zn2 O6 H6B 100.2 . . ?
H6A O6 H6B 107.7 . . ?
Zn2 O7 H7A 132.2 . . ?
Zn2 O7 H7B 120.0 . . ?
H7A O7 H7B 107.7 . . ?
H8A O8 H8B 116.4 . . ?
N6 Zn1 O1 110.7(3) . . ?
N6 Zn1 N4 115.7(3) . . ?
O1 Zn1 N4 105.8(3) . . ?
N6 Zn1 N1 114.0(3) . . ?
O1 Zn1 N1 98.2(2) . . ?
N4 Zn1 N1 110.7(3) . . ?
O7 Zn2 O5 115.3(3) . . ?
O7 Zn2 N9 120.3(3) . . ?
O5 Zn2 N9 124.4(3) . . ?
O7 Zn2 O3 91.3(3) . . ?
O5 Zn2 O3 86.8(2) . . ?
N9 Zn2 O3 91.6(2) . . ?
O7 Zn2 O6 90.8(3) . . ?
O5 Zn2 O6 89.7(2) . . ?
N9 Zn2 O6 89.7(3) . . ?
O3 Zn2 O6 176.4(3) . . ?

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
O2 C1 C2 C4 -23.4(12) . . . 4_575 ?
O1 C1 C2 C4 158.6(8) . . . 4_575 ?
O2 C1 C2 C3 155.0(8) . . . . ?
O1 C1 C2 C3 -23.0(11) . . . . ?
C4 C2 C3 C4 0.0(13) 4_575 . . 2 ?
C1 C2 C3 C4 -178.4(7) . . . 2 ?
C2 C4 C5 O4 -121.6(10) 4_576 . . . ?
C3 C4 C5 O4 62.3(12) 2_545 . . . ?
C2 C4 C5 O3 63.5(11) 4_576 . . . ?
C3 C4 C5 O3 -112.6(9) 2_545 . . . ?
N1 N2 N3 N4 -0.3(10) 2_645 . . . ?
N1 C6 N4 N3 0.8(9) 2_645 . . . ?
N5 C6 N4 N3 177.1(7) . . . . ?
N1 C6 N4 Zn1 -176.7(6) 2_645 . . . ?
N5 C6 N4 Zn1 -0.3(13) . . . . ?
N2 N3 N4 C6 -0.3(9) . . . . ?
N2 N3 N4 Zn1 177.8(6) . . . . ?
N9 C7 N6 N7 0.9(9) . . . . ?
N10 C7 N6 N7 -177.1(8) . . . . ?
N9 C7 N6 Zn1 -155.1(6) . . . . ?
N10 C7 N6 Zn1 26.9(13) . . . . ?
C7 N6 N7 N8 -1.0(9) . . . . ?
Zn1 N6 N7 N8 159.7(5) . . . . ?
N6 N7 N8 N9 0.7(9) . . . . ?
N6 C7 N9 N8 -0.6(9) . . . . ?
N10 C7 N9 N8 177.4(8) . . . . ?
N6 C7 N9 Zn2 168.5(6) . . . . ?
N10 C7 N9 Zn2 -13.5(13) . . . . ?
N7 N8 N9 C7 -0.1(9) . . . . ?
N7 N8 N9 Zn2 -171.0(5) . . . . ?
O2 C1 O1 Zn1 7.6(11) . . . . ?
C2 C1 O1 Zn1 -174.5(5) . . . . ?
O4 C5 O3 Zn2 14.3(13) . . . . ?
C4 C5 O3 Zn2 -171.0(5) . . . . ?
C7 N6 Zn1 O1 76.2(8) . . . . ?
N7 N6 Zn1 O1 -77.5(6) . . . . ?
C7 N6 Zn1 N4 -44.1(8) . . . . ?
N7 N6 Zn1 N4 162.3(5) . . . . ?
C7 N6 Zn1 N1 -174.2(7) . . . . ?
N7 N6 Zn1 N1 32.2(6) . . . . ?
C1 O1 Zn1 N6 -60.8(6) . . . . ?
C1 O1 Zn1 N4 65.2(6) . . . . ?
C1 O1 Zn1 N1 179.5(6) . . . . ?
C6 N4 Zn1 N6 -163.8(7) . . . . ?
N3 N4 Zn1 N6 18.9(7) . . . . ?
C6 N4 Zn1 O1 73.3(8) . . . . ?
N3 N4 Zn1 O1 -104.0(6) . . . . ?
C6 N4 Zn1 N1 -32.1(9) . . . . ?
N3 N4 Zn1 N1 150.6(5) . . . . ?
C6 N1 Zn1 N6 -32.0(9) 2_655 . . . ?
N2 N1 Zn1 N6 166.4(5) 2_655 . . . ?
C6 N1 Zn1 O1 85.1(8) 2_655 . . . ?
N2 N1 Zn1 O1 -76.5(6) 2_655 . . . ?
C6 N1 Zn1 N4 -164.5(8) 2_655 . . . ?
N2 N1 Zn1 N4 33.8(6) 2_655 . . . ?
C7 N9 Zn2 O7 -106.6(8) . . . . ?
N8 N9 Zn2 O7 61.2(7) . . . . ?
C7 N9 Zn2 O5 73.0(9) . . . . ?
N8 N9 Zn2 O5 -119.2(6) . . . . ?
C7 N9 Zn2 O3 -14.1(8) . . . . ?
N8 N9 Zn2 O3 153.6(6) . . . . ?
C7 N9 Zn2 O6 162.5(8) . . . . ?
N8 N9 Zn2 O6 -29.7(6) . . . . ?
C5 O3 Zn2 O7 -47.7(7) . . . . ?
C5 O3 Zn2 O5 67.6(7) . . . . ?
C5 O3 Zn2 N9 -168.1(7) . . . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
O8 H8B N5 0.85 2.29 3.087(10) 154.9 .
O8 H8A O1 0.85 2.09 2.896(9) 158.5 .
O7 H7B O3 0.85 2.27 3.099(10) 165.4 3_576
O7 H7A O2 0.85 1.98 2.786(9) 157.4 3_576
O6 H6B O1 0.85 2.63 3.176(8) 123.5 4_586
O6 H6B N8 0.85 2.27 2.944(9) 136.4 .
O6 H6A N7 0.85 2.67 3.388(9) 143.7 4_586
O6 H6A O4 0.85 2.16 2.664(9) 117.7 2_556
O5 H5D O8 0.86 1.81 2.657(9) 169.8 1_556
O5 H5C O2 0.83 2.13 2.951(9) 171.4 4_576
N10 H10B N3 0.88 2.17 3.019(9) 162.7 .
N10 H10A O3 0.88 2.19 2.847(9) 130.7 .
N5 H5B N2 0.88 2.10 2.912(9) 153.4 2_655
N5 H5A N7 0.88 2.19 3.039(9) 161.1 2_645

_diffrn_measured_fraction_theta_max 0.997
_diffrn_reflns_theta_full        25.00
_diffrn_measured_fraction_theta_full 0.997
_refine_diff_density_max         0.854
_refine_diff_density_min         -1.080
_refine_diff_density_rms         0.152
_database_code_depnum_ccdc_archive 'CCDC 1022209'
#######################################################################
#
#                 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_2

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C16 H14 N12 O10 Zn3'
_chemical_formula_weight         730.56

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                   19.474(4)
_cell_length_b                   9.849(2)
_cell_length_c                   12.064(2)
_cell_angle_alpha                90.00
_cell_angle_beta                 96.55(3)
_cell_angle_gamma                90.00
_cell_volume                     2298.8(8)
_cell_formula_units_Z            4
_cell_measurement_temperature    153(2)
_cell_measurement_reflns_used    9035
_cell_measurement_theta_min      3.4
_cell_measurement_theta_max      27.50

_exptl_crystal_description       Block
_exptl_crystal_colour            Colorless
_exptl_crystal_size_max          0.20
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.20
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    2.111
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1456
_exptl_absorpt_coefficient_mu    3.190
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.5679
_exptl_absorpt_correction_T_max  0.5679
_exptl_absorpt_process_details   sadabs

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      153(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 P4'
_diffrn_measurement_method       'ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            11006
_diffrn_reflns_av_R_equivalents  0.0423
_diffrn_reflns_av_sigmaI/netI    0.0345
_diffrn_reflns_limit_h_min       -25
_diffrn_reflns_limit_h_max       22
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_theta_min         3.40
_diffrn_reflns_theta_max         27.49
_reflns_number_total             2623
_reflns_number_gt                2254
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'Bruker XSCANS'
_computing_cell_refinement       'Bruker XSCANS'
_computing_data_reduction        'Bruker SHELXTL'
_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)+(0.0282P)²+2.8826P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         2623
_refine_ls_number_parameters     187
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0348
_refine_ls_R_factor_gt           0.0268
_refine_ls_wR_factor_ref         0.0650
_refine_ls_wR_factor_gt          0.0620
_refine_ls_goodness_of_fit_ref   1.052
_refine_ls_restrained_S_all      1.052
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
Zn1 Zn 0.5000 0.5000 1.0000 0.01569(10) Uani 1 2 d S . .
Zn2 Zn 0.315531(14) 0.75007(3) 0.371289(19) 0.01631(9) Uani 1 1 d . . .
O1 O 0.47628(8) 0.65551(17) 1.10092(12) 0.0186(3) Uani 1 1 d . . .
O2 O 0.41631(10) 0.8478(2) 1.10051(13) 0.0309(4) Uani 1 1 d . . .
O3 O 0.33004(9) 0.77540(17) 0.53261(12) 0.0209(4) Uani 1 1 d . . .
O4 O 0.40616(9) 0.60923(18) 0.52598(12) 0.0230(4) Uani 1 1 d . . .
O5 O 0.40623(9) 0.79628(18) 0.31490(13) 0.0240(4) Uani 1 1 d . . .
H5A H 0.4422 0.7540 0.3457 0.036 Uiso 1 1 d R . .
H5B H 0.4061 0.8064 0.2442 0.036 Uiso 1 1 d R . .
N1 N 0.43991(9) 0.6250(2) 0.87952(13) 0.0148(4) Uani 1 1 d . . .
N2 N 0.28487(10) 0.58717(19) 0.28251(14) 0.0164(4) Uani 1 1 d . . .
N3 N 0.28660(11) 0.6075(2) 0.17036(15) 0.0225(4) Uani 1 1 d . . .
N4 N 0.26038(11) 0.5040(2) 0.11718(15) 0.0201(4) Uani 1 1 d . . .
N5 N 0.23993(10) 0.41088(19) 0.18989(14) 0.0149(4) Uani 1 1 d . . .
N6 N 0.24650(13) 0.4041(2) 0.38767(15) 0.0310(5) Uani 1 1 d . . .
H6A H 0.2470 0.4499 0.4480 0.037 Uiso 1 1 d R . .
H6B H 0.2289 0.3247 0.3885 0.037 Uiso 1 1 d R . .
C1 C 0.42607(12) 0.7448(2) 0.92638(18) 0.0164(5) Uani 1 1 d . . .
C2 C 0.43989(12) 0.7509(2) 1.05294(18) 0.0181(5) Uani 1 1 d . . .
C3 C 0.40074(13) 0.8564(3) 0.86525(18) 0.0232(5) Uani 1 1 d . . .
H3 H 0.3931 0.9402 0.9009 0.028 Uiso 1 1 calc R . .
C4 C 0.38671(12) 0.8425(3) 0.75015(18) 0.0206(5) Uani 1 1 d . . .
H4 H 0.3706 0.9179 0.7054 0.025 Uiso 1 1 calc R . .
C5 C 0.39658(11) 0.7172(2) 0.70146(17) 0.0153(4) Uani 1 1 d . . .
C6 C 0.37756(11) 0.6970(2) 0.57840(17) 0.0148(4) Uani 1 1 d . . .
C7 C 0.42397(11) 0.6107(2) 0.76885(16) 0.0147(4) Uani 1 1 d . . .
H7 H 0.4316 0.5255 0.7354 0.018 Uiso 1 1 calc R . .
C15 C 0.25634(11) 0.4649(2) 0.29215(17) 0.0144(4) Uani 1 1 d . . .


_geom_special_details            
; 
 All esds (except the esd in the dihedral angle between two l.s. planes) 
 are estimated using the full covariance matrix.  The cell esds are taken 
 into account individually in the estimation of esds in distances, angles 
 and torsion angles; correlations between esds in cell parameters are only 
 used when they are defined by crystal symmetry.  An approximate (isotropic) 
 treatment of cell esds is used for estimating esds involving l.s. planes. 
;

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Zn1 O1 2.0420(16) 5_667 ?
Zn1 O1 2.0420(16) . ?
Zn1 N1 2.1467(18) 5_667 ?
Zn1 N1 2.1467(18) . ?
Zn1 O4 2.1738(17) 2_656 ?
Zn1 O4 2.1738(17) 6_566 ?
Zn2 O3 1.9505(15) . ?
Zn2 N2 1.9828(19) . ?
Zn2 N5 2.0095(19) 4 ?
Zn2 O5 2.0158(18) . ?
O1 C2 1.275(3) . ?
O2 C2 1.229(3) . ?
O3 C6 1.281(3) . ?
O4 C6 1.240(3) . ?
O4 Zn1 2.1738(17) 2_656 ?
O5 H5A 0.8619 . ?
O5 H5B 0.8581 . ?
N1 C7 1.343(3) . ?
N1 C1 1.349(3) . ?
N2 C15 1.337(3) . ?
N2 N3 1.372(2) . ?
N3 N4 1.279(3) . ?
N4 N5 1.360(3) . ?
N5 C15 1.348(3) . ?
N5 Zn2 2.0095(19) 4_545 ?
N6 C15 1.332(3) . ?
N6 H6A 0.8551 . ?
N6 H6B 0.8542 . ?
C1 C3 1.383(3) . ?
C1 C2 1.521(3) . ?
C3 C4 1.391(3) . ?
C3 H3 0.9500 . ?
C4 C5 1.390(3) . ?
C4 H4 0.9500 . ?
C5 C7 1.395(3) . ?
C5 C6 1.502(3) . ?
C7 H7 0.9500 . ?

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
O1 Zn1 O1 180.0 5_667 . ?
O1 Zn1 N1 80.26(6) 5_667 5_667 ?
O1 Zn1 N1 99.74(6) . 5_667 ?
O1 Zn1 N1 99.74(6) 5_667 . ?
O1 Zn1 N1 80.26(6) . . ?
N1 Zn1 N1 180.000(1) 5_667 . ?
O1 Zn1 O4 91.96(7) 5_667 2_656 ?
O1 Zn1 O4 88.04(7) . 2_656 ?
N1 Zn1 O4 88.80(7) 5_667 2_656 ?
N1 Zn1 O4 91.20(7) . 2_656 ?
O1 Zn1 O4 88.04(7) 5_667 6_566 ?
O1 Zn1 O4 91.96(7) . 6_566 ?
N1 Zn1 O4 91.20(7) 5_667 6_566 ?
N1 Zn1 O4 88.80(7) . 6_566 ?
O4 Zn1 O4 180.0 2_656 6_566 ?
O3 Zn2 N2 130.01(7) . . ?
O3 Zn2 N5 106.04(7) . 4 ?
N2 Zn2 N5 108.86(8) . 4 ?
O3 Zn2 O5 105.97(7) . . ?
N2 Zn2 O5 102.82(8) . . ?
N5 Zn2 O5 98.80(7) 4 . ?
C2 O1 Zn1 115.71(13) . . ?
C6 O3 Zn2 111.62(14) . . ?
C6 O4 Zn1 148.47(15) . 2_656 ?
Zn2 O5 H5A 116.5 . . ?
Zn2 O5 H5B 117.3 . . ?
H5A O5 H5B 113.2 . . ?
C7 N1 C1 118.27(19) . . ?
C7 N1 Zn1 131.25(15) . . ?
C1 N1 Zn1 109.72(13) . . ?
C15 N2 N3 105.94(17) . . ?
C15 N2 Zn2 141.67(14) . . ?
N3 N2 Zn2 112.00(14) . . ?
N4 N3 N2 108.94(18) . . ?
N3 N4 N5 110.10(17) . . ?
C15 N5 N4 105.53(18) . . ?
C15 N5 Zn2 135.12(15) . 4_545 ?
N4 N5 Zn2 118.65(13) . 4_545 ?
C15 N6 H6A 120.7 . . ?
C15 N6 H6B 121.3 . . ?
H6A N6 H6B 116.0 . . ?
N1 C1 C3 123.2(2) . . ?
N1 C1 C2 115.75(19) . . ?
C3 C1 C2 121.0(2) . . ?
O2 C2 O1 125.3(2) . . ?
O2 C2 C1 117.8(2) . . ?
O1 C2 C1 116.9(2) . . ?
C1 C3 C4 118.2(2) . . ?
C1 C3 H3 120.9 . . ?
C4 C3 H3 120.9 . . ?
C5 C4 C3 119.2(2) . . ?
C5 C4 H4 120.4 . . ?
C3 C4 H4 120.4 . . ?
C4 C5 C7 118.92(19) . . ?
C4 C5 C6 120.3(2) . . ?
C7 C5 C6 120.8(2) . . ?
O4 C6 O3 123.00(19) . . ?
O4 C6 C5 121.5(2) . . ?
O3 C6 C5 115.5(2) . . ?
N1 C7 C5 122.0(2) . . ?
N1 C7 H7 119.0 . . ?
C5 C7 H7 119.0 . . ?
N6 C15 N2 125.62(19) . . ?
N6 C15 N5 124.9(2) . . ?
N2 C15 N5 109.48(18) . . ?

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 Zn1 O1 C2 179.56(16) 5_667 . . . ?
N1 Zn1 O1 C2 -0.44(16) . . . . ?
O4 Zn1 O1 C2 91.11(17) 2_656 . . . ?
O4 Zn1 O1 C2 -88.89(17) 6_566 . . . ?
N2 Zn2 O3 C6 62.07(19) . . . . ?
N5 Zn2 O3 C6 -165.06(15) 4 . . . ?
O5 Zn2 O3 C6 -60.71(17) . . . . ?
O1 Zn1 N1 C7 -2.4(2) 5_667 . . . ?
O1 Zn1 N1 C7 177.6(2) . . . . ?
O4 Zn1 N1 C7 89.8(2) 2_656 . . . ?
O4 Zn1 N1 C7 -90.2(2) 6_566 . . . ?
O1 Zn1 N1 C1 -171.91(15) 5_667 . . . ?
O1 Zn1 N1 C1 8.09(15) . . . . ?
O4 Zn1 N1 C1 -79.71(15) 2_656 . . . ?
O4 Zn1 N1 C1 100.29(15) 6_566 . . . ?
O3 Zn2 N2 C15 13.7(3) . . . . ?
N5 Zn2 N2 C15 -118.2(3) 4 . . . ?
O5 Zn2 N2 C15 137.7(3) . . . . ?
O3 Zn2 N2 N3 -174.93(13) . . . . ?
N5 Zn2 N2 N3 53.17(17) 4 . . . ?
O5 Zn2 N2 N3 -50.92(16) . . . . ?
C15 N2 N3 N4 0.3(3) . . . . ?
Zn2 N2 N3 N4 -174.10(15) . . . . ?
N2 N3 N4 N5 0.2(3) . . . . ?
N3 N4 N5 C15 -0.6(3) . . . . ?
N3 N4 N5 Zn2 171.25(15) . . . 4_545 ?
C7 N1 C1 C3 -4.6(3) . . . . ?
Zn1 N1 C1 C3 166.5(2) . . . . ?
C7 N1 C1 C2 175.25(19) . . . . ?
Zn1 N1 C1 C2 -13.7(2) . . . . ?
Zn1 O1 C2 O2 174.5(2) . . . . ?
Zn1 O1 C2 C1 -6.8(3) . . . . ?
N1 C1 C2 O2 -166.7(2) . . . . ?
C3 C1 C2 O2 13.1(3) . . . . ?
N1 C1 C2 O1 14.5(3) . . . . ?
C3 C1 C2 O1 -165.7(2) . . . . ?
N1 C1 C3 C4 2.3(4) . . . . ?
C2 C1 C3 C4 -177.6(2) . . . . ?
C1 C3 C4 C5 1.9(4) . . . . ?
C3 C4 C5 C7 -3.5(3) . . . . ?
C3 C4 C5 C6 176.1(2) . . . . ?
Zn1 O4 C6 O3 142.9(2) 2_656 . . . ?
Zn1 O4 C6 C5 -37.6(4) 2_656 . . . ?
Zn2 O3 C6 O4 -5.3(3) . . . . ?
Zn2 O3 C6 C5 175.15(15) . . . . ?
C4 C5 C6 O4 154.2(2) . . . . ?
C7 C5 C6 O4 -26.2(3) . . . . ?
C4 C5 C6 O3 -26.2(3) . . . . ?
C7 C5 C6 O3 153.4(2) . . . . ?
C1 N1 C7 C5 2.8(3) . . . . ?
Zn1 N1 C7 C5 -166.01(16) . . . . ?
C4 C5 C7 N1 1.2(3) . . . . ?
C6 C5 C7 N1 -178.4(2) . . . . ?
N3 N2 C15 N6 178.3(2) . . . . ?
Zn2 N2 C15 N6 -10.1(4) . . . . ?
N3 N2 C15 N5 -0.7(3) . . . . ?
Zn2 N2 C15 N5 170.95(19) . . . . ?
N4 N5 C15 N6 -178.2(2) . . . . ?
Zn2 N5 C15 N6 12.0(4) 4_545 . . . ?
N4 N5 C15 N2 0.8(2) . . . . ?
Zn2 N5 C15 N2 -169.04(16) 4_545 . . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
N6 H6B N3 0.85 2.26 3.055(3) 154.2 4_545
N6 H6A N4 0.86 2.08 2.896(3) 159.8 6_566
O5 H5B O2 0.86 1.81 2.665(2) 171.0 1_554
O5 H5A O1 0.86 1.91 2.768(2) 174.2 2_656

_diffrn_measured_fraction_theta_max 0.998
_diffrn_reflns_theta_full        27.49
_diffrn_measured_fraction_theta_full 0.998
_refine_diff_density_max         0.502
_refine_diff_density_min         -0.550
_refine_diff_density_rms         0.082
_database_code_depnum_ccdc_archive 'CCDC 1022210'
