# Electronic Supplementary Material (ESI) for CrystEngComm.
# 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_1

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C36 H24 N14 O10 Zn5'
_chemical_formula_weight         1139.54

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                   7.6058(6)
_cell_length_b                   10.2154(7)
_cell_length_c                   12.2851(12)
_cell_angle_alpha                102.799(5)
_cell_angle_beta                 97.934(5)
_cell_angle_gamma                98.974(5)
_cell_volume                     904.52(13)
_cell_formula_units_Z            1
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    ?
_cell_measurement_theta_min      ?
_cell_measurement_theta_max      ?

_exptl_crystal_description       columnar
_exptl_crystal_colour            colorless
_exptl_crystal_size_max          0.11
_exptl_crystal_size_mid          0.10
_exptl_crystal_size_min          0.10
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    2.092
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             568
_exptl_absorpt_coefficient_mu    3.353
_exptl_absorpt_correction_type   empirical
_exptl_absorpt_correction_T_min  0.698
_exptl_absorpt_correction_T_max  0.715
_exptl_absorpt_process_details   Process-auto

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      293(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Rigaku RAXIS-RAPID'
_diffrn_measurement_method       omega-scan
_diffrn_detector_area_resol_mean 10.0
_diffrn_standards_number         0
_diffrn_standards_interval_count 0
_diffrn_standards_interval_time  0
_diffrn_standards_decay_%        0
_diffrn_reflns_number            5047
_diffrn_reflns_av_R_equivalents  0.0249
_diffrn_reflns_av_sigmaI/netI    0.0256
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_limit_l_max       10
_diffrn_reflns_theta_min         1.73
_diffrn_reflns_theta_max         25.02
_reflns_number_total             3140
_reflns_number_gt                2930
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       Process-auto
_computing_cell_refinement       Process-auto
_computing_data_reduction        Process-auto
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    ?
_computing_publication_material  ?

_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)+(0.0550P)²+5.8277P] 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         3140
_refine_ls_number_parameters     299
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0395
_refine_ls_R_factor_gt           0.0373
_refine_ls_wR_factor_ref         0.1310
_refine_ls_wR_factor_gt          0.1299
_refine_ls_goodness_of_fit_ref   1.183
_refine_ls_restrained_S_all      1.183
_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 -0.5000 0.0275(3) Uani 1 2 d S . .
Zn2 Zn -0.56441(8) -0.84077(6) -0.57600(5) 0.0166(2) Uani 1 1 d . . .
Zn3 Zn -0.84992(8) -0.68160(6) -0.70965(5) 0.0180(2) Uani 1 1 d . . .
O1 O -0.2450(6) -0.4544(4) -0.2189(4) 0.0281(10) Uani 1 1 d . . .
O2 O -0.5671(5) -0.9834(4) -0.3874(3) 0.0202(8) Uani 1 1 d . . .
O3 O -0.8660(6) -0.8752(4) -0.7917(3) 0.0230(9) Uani 1 1 d . . .
O4 O -1.0318(6) -1.2507(4) -0.5600(4) 0.0297(10) Uani 1 1 d . . .
O5 O -0.6993(5) -0.6651(4) -0.5639(3) 0.0178(8) Uani 1 1 d . . .
N1 N -0.4050(6) -0.6291(4) -0.3672(4) 0.0194(10) Uani 1 1 d . . .
N2 N -0.4815(6) -0.7697(4) -0.4079(4) 0.0170(9) Uani 1 1 d . . .
N3 N -0.8101(6) -0.9640(4) -0.6401(4) 0.0179(10) Uani 1 1 d . . .
N4 N -0.8610(6) -1.0634(5) -0.5834(4) 0.0181(10) Uani 1 1 d . . .
H4A H -0.7999 -1.0537 -0.5168 0.022 Uiso 1 1 calc R . .
N5 N -1.1053(6) -0.6758(5) -0.6855(4) 0.0199(10) Uani 1 1 d . . .
N6 N -1.3312(6) -0.6017(5) -0.6085(4) 0.0201(10) Uani 1 1 d . . .
N7 N -1.3744(6) -0.7436(4) -0.6453(4) 0.0190(10) Uani 1 1 d . . .
C1 C -0.2211(9) -0.7104(7) 0.0003(5) 0.0328(15) Uani 1 1 d . . .
H1A H -0.1613 -0.6776 0.0751 0.039 Uiso 1 1 calc R . .
C2 C -0.3138(9) -0.8465(7) -0.0383(6) 0.0310(14) Uani 1 1 d . . .
H2A H -0.3167 -0.9031 0.0114 0.037 Uiso 1 1 calc R . .
C3 C -0.4005(8) -0.8969(6) -0.1494(5) 0.0224(12) Uani 1 1 d . . .
H3A H -0.4607 -0.9876 -0.1748 0.027 Uiso 1 1 calc R . .
C4 C -0.3978(8) -0.8109(6) -0.2246(5) 0.0192(11) Uani 1 1 d . . .
C5 C -0.3085(8) -0.6747(6) -0.1852(5) 0.0197(11) Uani 1 1 d . . .
C6 C -0.2183(9) -0.6251(6) -0.0723(5) 0.0271(13) Uani 1 1 d . . .
H6A H -0.1567 -0.5348 -0.0465 0.033 Uiso 1 1 calc R . .
C7 C -0.3186(7) -0.5840(5) -0.2621(5) 0.0180(11) Uani 1 1 d . . .
C8 C -0.4849(7) -0.8575(5) -0.3423(5) 0.0181(11) Uani 1 1 d . . .
C9 C -1.2182(8) -1.3092(6) -0.7932(6) 0.0292(14) Uani 1 1 d . . .
H9A H -1.2514 -1.3742 -0.7538 0.035 Uiso 1 1 calc R . .
C10 C -1.2961(9) -1.3286(7) -0.9048(6) 0.0344(16) Uani 1 1 d . . .
H10A H -1.3805 -1.4079 -0.9410 0.041 Uiso 1 1 calc R . .
C11 C -1.2497(9) -1.2308(7) -0.9637(6) 0.0333(15) Uani 1 1 d . . .
H11A H -1.3020 -1.2452 -1.0395 0.040 Uiso 1 1 calc R . .
C12 C -1.1259(8) -1.1123(7) -0.9100(5) 0.0272(13) Uani 1 1 d . . .
H12A H -1.0973 -1.0460 -0.9492 0.033 Uiso 1 1 calc R . .
C13 C -1.0438(7) -1.0915(5) -0.7973(5) 0.0196(12) Uani 1 1 d . . .
C14 C -1.0891(8) -1.1913(6) -0.7392(5) 0.0214(12) Uani 1 1 d . . .
C15 C -0.9030(7) -0.9706(5) -0.7408(5) 0.0178(11) Uani 1 1 d . . .
C16 C -0.9958(8) -1.1730(6) -0.6219(5) 0.0218(12) Uani 1 1 d . . .
C17 C -1.1706(8) -0.5666(6) -0.6319(5) 0.0197(12) Uani 1 1 d . . .
H17A H -1.1075 -0.4767 -0.6139 0.024 Uiso 1 1 calc R . .
C18 C -1.2374(8) -0.7830(6) -0.6909(5) 0.0211(12) Uani 1 1 d . . .
H18A H -1.2327 -0.8737 -0.7227 0.025 Uiso 1 1 calc R . .
H0 H -0.760(14) -0.681(10) -0.514(9) 0.07(3) 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
Zn1 O5 2.011(4) 2_444 ?
Zn1 O5 2.011(4) . ?
Zn1 N6 2.186(5) 2_344 ?
Zn1 N6 2.186(5) 1_655 ?
Zn1 N1 2.418(5) . ?
Zn1 N1 2.418(5) 2_444 ?
Zn2 N2 2.006(5) . ?
Zn2 N7 2.016(5) 1_655 ?
Zn2 N3 2.029(5) . ?
Zn2 O2 2.180(4) 2_434 ?
Zn2 O5 2.190(4) . ?
Zn3 O1 1.904(4) 2_444 ?
Zn3 O5 1.946(4) . ?
Zn3 O3 1.987(4) . ?
Zn3 N5 2.012(5) . ?
O1 C7 1.313(7) . ?
O1 Zn3 1.904(4) 2_444 ?
O2 C8 1.300(7) . ?
O2 Zn2 2.180(4) 2_434 ?
O3 C15 1.286(7) . ?
O4 C16 1.241(7) . ?
N1 C7 1.311(7) . ?
N1 N2 1.411(6) . ?
N2 C8 1.332(7) . ?
N3 C15 1.319(8) . ?
N3 N4 1.390(6) . ?
N4 C16 1.342(7) . ?
N5 C18 1.349(7) . ?
N5 C17 1.366(7) . ?
N6 C17 1.307(8) . ?
N6 N7 1.391(6) . ?
N6 Zn1 2.186(5) 1_455 ?
N7 C18 1.324(8) . ?
N7 Zn2 2.016(5) 1_455 ?
C1 C6 1.378(9) . ?
C1 C2 1.401(10) . ?
C2 C3 1.377(9) . ?
C3 C4 1.409(8) . ?
C4 C5 1.395(8) . ?
C4 C8 1.445(8) . ?
C5 C6 1.403(8) . ?
C5 C7 1.465(8) . ?
C9 C10 1.373(10) . ?
C9 C14 1.397(8) . ?
C10 C11 1.389(10) . ?
C11 C12 1.381(9) . ?
C12 C13 1.393(9) . ?
C13 C14 1.397(8) . ?
C13 C15 1.469(8) . ?
C14 C16 1.473(9) . ?

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
O5 Zn1 O5 180.00(17) 2_444 . ?
O5 Zn1 N6 88.38(17) 2_444 2_344 ?
O5 Zn1 N6 91.62(17) . 2_344 ?
O5 Zn1 N6 91.62(17) 2_444 1_655 ?
O5 Zn1 N6 88.38(17) . 1_655 ?
N6 Zn1 N6 180.000(1) 2_344 1_655 ?
O5 Zn1 N1 96.22(16) 2_444 . ?
O5 Zn1 N1 83.78(16) . . ?
N6 Zn1 N1 93.63(17) 2_344 . ?
N6 Zn1 N1 86.37(17) 1_655 . ?
O5 Zn1 N1 83.78(16) 2_444 2_444 ?
O5 Zn1 N1 96.22(16) . 2_444 ?
N6 Zn1 N1 86.37(17) 2_344 2_444 ?
N6 Zn1 N1 93.63(17) 1_655 2_444 ?
N1 Zn1 N1 180.000(1) . 2_444 ?
N2 Zn2 N7 104.95(19) . 1_655 ?
N2 Zn2 N3 120.72(19) . . ?
N7 Zn2 N3 133.82(19) 1_655 . ?
N2 Zn2 O2 101.75(17) . 2_434 ?
N7 Zn2 O2 86.57(17) 1_655 2_434 ?
N3 Zn2 O2 90.36(17) . 2_434 ?
N2 Zn2 O5 85.57(17) . . ?
N7 Zn2 O5 88.95(17) 1_655 . ?
N3 Zn2 O5 88.14(17) . . ?
O2 Zn2 O5 172.21(15) 2_434 . ?
O1 Zn3 O5 111.14(18) 2_444 . ?
O1 Zn3 O3 116.55(17) 2_444 . ?
O5 Zn3 O3 103.61(16) . . ?
O1 Zn3 N5 113.2(2) 2_444 . ?
O5 Zn3 N5 108.52(19) . . ?
O3 Zn3 N5 102.98(18) . . ?
C7 O1 Zn3 130.3(4) . 2_444 ?
C8 O2 Zn2 125.6(3) . 2_434 ?
C15 O3 Zn3 119.4(3) . . ?
Zn3 O5 Zn1 118.8(2) . . ?
Zn3 O5 Zn2 108.98(18) . . ?
Zn1 O5 Zn2 105.08(17) . . ?
C7 N1 N2 118.7(4) . . ?
C7 N1 Zn1 128.9(4) . . ?
N2 N1 Zn1 111.6(3) . . ?
C8 N2 N1 123.4(5) . . ?
C8 N2 Zn2 119.3(4) . . ?
N1 N2 Zn2 117.1(3) . . ?
C15 N3 N4 119.4(5) . . ?
C15 N3 Zn2 123.3(4) . . ?
N4 N3 Zn2 116.0(3) . . ?
C16 N4 N3 126.7(5) . . ?
C18 N5 C17 102.9(5) . . ?
C18 N5 Zn3 127.2(4) . . ?
C17 N5 Zn3 127.8(4) . . ?
C17 N6 N7 105.6(4) . . ?
C17 N6 Zn1 135.0(4) . 1_455 ?
N7 N6 Zn1 117.7(3) . 1_455 ?
C18 N7 N6 106.7(4) . . ?
C18 N7 Zn2 132.2(4) . 1_455 ?
N6 N7 Zn2 117.0(3) . 1_455 ?
C6 C1 C2 120.2(6) . . ?
C3 C2 C1 120.5(6) . . ?
C2 C3 C4 119.9(6) . . ?
C5 C4 C3 119.5(5) . . ?
C5 C4 C8 117.8(5) . . ?
C3 C4 C8 122.7(5) . . ?
C4 C5 C6 120.1(5) . . ?
C4 C5 C7 118.8(5) . . ?
C6 C5 C7 121.1(5) . . ?
C1 C6 C5 119.9(6) . . ?
N1 C7 O1 121.8(5) . . ?
N1 C7 C5 121.4(5) . . ?
O1 C7 C5 116.7(5) . . ?
O2 C8 N2 118.2(5) . . ?
O2 C8 C4 122.3(5) . . ?
N2 C8 C4 119.5(5) . . ?
C10 C9 C14 119.8(6) . . ?
C9 C10 C11 120.5(6) . . ?
C12 C11 C10 120.1(6) . . ?
C11 C12 C13 120.3(6) . . ?
C12 C13 C14 119.3(5) . . ?
C12 C13 C15 121.3(5) . . ?
C14 C13 C15 119.4(5) . . ?
C13 C14 C9 120.0(6) . . ?
C13 C14 C16 119.5(5) . . ?
C9 C14 C16 120.5(6) . . ?
O3 C15 N3 120.6(5) . . ?
O3 C15 C13 119.8(5) . . ?
N3 C15 C13 119.5(5) . . ?
O4 C16 N4 119.9(6) . . ?
O4 C16 C14 125.1(5) . . ?
N4 C16 C14 115.1(5) . . ?
N6 C17 N5 112.8(5) . . ?
N7 C18 N5 111.9(5) . . ?

_diffrn_measured_fraction_theta_max 0.989
_diffrn_reflns_theta_full        25.02
_diffrn_measured_fraction_theta_full 0.989
_refine_diff_density_max         0.549
_refine_diff_density_min         -0.568
_refine_diff_density_rms         0.122
_database_code_depnum_ccdc_archive 'CCDC 953442'
#######################################################################
#
#                 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            'C20 H18 N14 O6 Zn3'
_chemical_formula_weight         746.59

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
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                   13.7823(7)
_cell_length_b                   9.7678(7)
_cell_length_c                   20.5058(17)
_cell_angle_alpha                90.00
_cell_angle_beta                 96.553(4)
_cell_angle_gamma                90.00
_cell_volume                     2742.5(3)
_cell_formula_units_Z            4
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    ?
_cell_measurement_theta_min      ?
_cell_measurement_theta_max      ?

_exptl_crystal_description       columnar
_exptl_crystal_colour            colorless
_exptl_crystal_size_max          0.12
_exptl_crystal_size_mid          0.11
_exptl_crystal_size_min          0.10
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.808
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1496
_exptl_absorpt_coefficient_mu    2.668
_exptl_absorpt_correction_type   empirical
_exptl_absorpt_correction_T_min  0.733
_exptl_absorpt_correction_T_max  0.766
_exptl_absorpt_process_details   SADABS

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      293(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean 9.00cm
_diffrn_standards_number         none
_diffrn_standards_interval_count none
_diffrn_standards_interval_time  none
_diffrn_standards_decay_%        none
_diffrn_reflns_number            7500
_diffrn_reflns_av_R_equivalents  0.0436
_diffrn_reflns_av_sigmaI/netI    0.0335
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_limit_l_max       24
_diffrn_reflns_theta_min         2.56
_diffrn_reflns_theta_max         24.98
_reflns_number_total             2405
_reflns_number_gt                2176
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'Bruker SMAR'
_computing_cell_refinement       'Bruker SMAR'
_computing_data_reduction        'Bruker SMAR'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    ?
_computing_publication_material  ?

_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)+(0.0470P)²+3.6758P] 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         2405
_refine_ls_number_parameters     195
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0332
_refine_ls_R_factor_gt           0.0297
_refine_ls_wR_factor_ref         0.0816
_refine_ls_wR_factor_gt          0.0793
_refine_ls_goodness_of_fit_ref   1.050
_refine_ls_restrained_S_all      1.050
_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
Zn1 Zn 0.18655(2) 0.12655(3) 0.668482(15) 0.02187(13) Uani 1 1 d . . .
Zn2 Zn 0.0000 0.05438(5) 0.7500 0.02379(14) Uani 1 2 d S . .
N1 N 0.20105(17) 0.0475(3) 0.57963(12) 0.0300(6) Uani 1 1 d . . .
N2 N 0.12553(18) 0.0235(3) 0.52960(12) 0.0360(6) Uani 1 1 d . . .
H2A H 0.0685 0.0523 0.5361 0.043 Uiso 1 1 calc R . .
N3 N 0.37744(16) 0.4462(2) 0.73074(13) 0.0304(6) Uani 1 1 d . . .
N4 N 0.29458(15) 0.4802(2) 0.76209(12) 0.0257(5) Uani 1 1 d . . .
N5 N 0.25921(16) 0.2985(2) 0.69756(12) 0.0263(5) Uani 1 1 d . . .
N6 N 0.1380(2) 0.3824(4) 0.75998(18) 0.0630(11) Uani 1 1 d . . .
H6A H 0.1204 0.4400 0.7881 0.076 Uiso 1 1 calc R . .
H6B H 0.0980 0.3202 0.7440 0.076 Uiso 1 1 calc R . .
N7 N 0.4118(2) 0.2838(4) 0.6526(2) 0.0773(14) Uani 1 1 d . . .
H7A H 0.4695 0.3163 0.6509 0.093 Uiso 1 1 calc R . .
H7B H 0.3920 0.2148 0.6286 0.093 Uiso 1 1 calc R . .
O1 O 0.35788(14) 0.0227(2) 0.61759(11) 0.0354(5) Uani 1 1 d . . .
O2 O 0.05792(16) -0.0604(3) 0.43304(11) 0.0520(7) Uani 1 1 d . . .
OH1 O 0.04764(13) 0.1639(2) 0.67998(9) 0.0252(4) Uani 1 1 d . . .
C1 C 0.4012(2) -0.1096(4) 0.50107(18) 0.0438(8) Uani 1 1 d . . .
H1A H 0.4528 -0.0992 0.5341 0.053 Uiso 1 1 calc R . .
C2 C 0.4164(3) -0.1701(5) 0.4433(2) 0.0602(11) Uani 1 1 d . . .
H2B H 0.4785 -0.2014 0.4374 0.072 Uiso 1 1 calc R . .
C3 C 0.3399(3) -0.1860(5) 0.39263(19) 0.0576(11) Uani 1 1 d . . .
H3B H 0.3518 -0.2251 0.3530 0.069 Uiso 1 1 calc R . .
C4 C 0.2476(3) -0.1435(4) 0.40173(17) 0.0445(8) Uani 1 1 d . . .
H4B H 0.1963 -0.1561 0.3687 0.053 Uiso 1 1 calc R . .
C5 C 0.2308(2) -0.0818(3) 0.46042(15) 0.0323(7) Uani 1 1 d . . .
C6 C 0.3076(2) -0.0627(3) 0.51069(15) 0.0303(6) Uani 1 1 d . . .
C7 C 0.2901(2) 0.0043(3) 0.57179(14) 0.0275(6) Uani 1 1 d . . .
C8 C 0.1330(2) -0.0394(4) 0.47282(15) 0.0352(7) Uani 1 1 d . . .
C9 C 0.3523(2) 0.3411(3) 0.69286(16) 0.0338(7) Uani 1 1 d . . .
C10 C 0.22763(19) 0.3897(3) 0.74104(15) 0.0287(6) 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 OH1 1.9892(17) . ?
Zn1 N1 2.010(2) . ?
Zn1 N5 2.011(2) . ?
Zn1 N4 2.013(2) 4_546 ?
Zn2 OH1 1.9627(19) 2_556 ?
Zn2 OH1 1.9627(19) . ?
Zn2 N3 1.994(2) 3_445 ?
Zn2 N3 1.994(2) 4_546 ?
N1 C7 1.325(4) . ?
N1 N2 1.395(3) . ?
N2 C8 1.331(4) . ?
N3 C9 1.310(4) . ?
N3 N4 1.413(3) . ?
N3 Zn2 1.994(2) 3 ?
N4 C10 1.315(4) . ?
N4 Zn1 2.013(2) 4_556 ?
N5 C9 1.362(3) . ?
N5 C10 1.366(4) . ?
N6 C10 1.339(4) . ?
N7 C9 1.350(4) . ?
O1 C7 1.260(4) . ?
O2 C8 1.259(4) . ?
C1 C2 1.361(5) . ?
C1 C6 1.403(4) . ?
C2 C3 1.402(6) . ?
C3 C4 1.372(5) . ?
C4 C5 1.389(4) . ?
C5 C6 1.403(4) . ?
C5 C8 1.460(4) . ?
C6 C7 1.458(4) . ?

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
OH1 Zn1 N1 112.00(9) . . ?
OH1 Zn1 N5 105.37(8) . . ?
N1 Zn1 N5 119.48(10) . . ?
OH1 Zn1 N4 95.44(8) . 4_546 ?
N1 Zn1 N4 110.50(10) . 4_546 ?
N5 Zn1 N4 111.32(10) . 4_546 ?
OH1 Zn2 OH1 113.94(12) 2_556 . ?
OH1 Zn2 N3 95.01(9) 2_556 3_445 ?
OH1 Zn2 N3 119.39(10) . 3_445 ?
OH1 Zn2 N3 119.39(10) 2_556 4_546 ?
OH1 Zn2 N3 95.01(9) . 4_546 ?
N3 Zn2 N3 115.96(15) 3_445 4_546 ?
C7 N1 N2 118.7(2) . . ?
C7 N1 Zn1 114.94(19) . . ?
N2 N1 Zn1 126.02(18) . . ?
C8 N2 N1 126.5(3) . . ?
C9 N3 N4 106.3(2) . . ?
C9 N3 Zn2 133.94(19) . 3 ?
N4 N3 Zn2 119.71(17) . 3 ?
C10 N4 N3 105.4(2) . . ?
C10 N4 Zn1 137.63(18) . 4_556 ?
N3 N4 Zn1 116.31(16) . 4_556 ?
C9 N5 C10 102.7(2) . . ?
C9 N5 Zn1 132.46(19) . . ?
C10 N5 Zn1 123.57(17) . . ?
Zn2 OH1 Zn1 113.18(9) . . ?
C2 C1 C6 120.0(3) . . ?
C1 C2 C3 121.0(3) . . ?
C4 C3 C2 119.8(3) . . ?
C3 C4 C5 119.9(3) . . ?
C4 C5 C6 120.5(3) . . ?
C4 C5 C8 121.5(3) . . ?
C6 C5 C8 118.0(3) . . ?
C1 C6 C5 118.8(3) . . ?
C1 C6 C7 120.8(3) . . ?
C5 C6 C7 120.4(3) . . ?
O1 C7 N1 118.8(3) . . ?
O1 C7 C6 121.6(3) . . ?
N1 C7 C6 119.6(3) . . ?
O2 C8 N2 120.2(3) . . ?
O2 C8 C5 123.2(3) . . ?
N2 C8 C5 116.6(3) . . ?
N3 C9 N7 123.3(3) . . ?
N3 C9 N5 112.6(2) . . ?
N7 C9 N5 124.0(3) . . ?
N4 C10 N6 125.2(3) . . ?
N4 C10 N5 112.9(2) . . ?
N6 C10 N5 121.9(3) . . ?

_diffrn_measured_fraction_theta_max 0.998
_diffrn_reflns_theta_full        24.98
_diffrn_measured_fraction_theta_full 0.998
_refine_diff_density_max         0.665
_refine_diff_density_min         -0.519
_refine_diff_density_rms         0.081
_database_code_depnum_ccdc_archive 'CCDC 953443'
#######################################################################
#
#                 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_3

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C10 H8 N12 O2 Zn2'
_chemical_formula_weight         459.02

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           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                   12.354(3)
_cell_length_b                   12.473(3)
_cell_length_c                   10.449(2)
_cell_angle_alpha                90.00
_cell_angle_beta                 116.92(3)
_cell_angle_gamma                90.00
_cell_volume                     1435.5(5)
_cell_formula_units_Z            4
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    ?
_cell_measurement_theta_min      ?
_cell_measurement_theta_max      ?

_exptl_crystal_description       columnar
_exptl_crystal_colour            colorless
_exptl_crystal_size_max          0.12
_exptl_crystal_size_mid          0.10
_exptl_crystal_size_min          0.10
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    2.124
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             912
_exptl_absorpt_coefficient_mu    3.383
_exptl_absorpt_correction_type   empirical
_exptl_absorpt_correction_T_min  0.673
_exptl_absorpt_correction_T_max  0.713
_exptl_absorpt_process_details   Process-auto

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      293(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Rigaku RAXIS-RAPID'
_diffrn_measurement_method       omega-scan
_diffrn_detector_area_resol_mean 10.0
_diffrn_standards_number         0
_diffrn_standards_interval_count 0
_diffrn_standards_interval_time  0
_diffrn_standards_decay_%        0
_diffrn_reflns_number            6966
_diffrn_reflns_av_R_equivalents  0.0193
_diffrn_reflns_av_sigmaI/netI    0.0147
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_theta_min         3.27
_diffrn_reflns_theta_max         27.43
_reflns_number_total             1640
_reflns_number_gt                1530
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       Process-auto
_computing_cell_refinement       Process-auto
_computing_data_reduction        Process-auto
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    ?
_computing_publication_material  ?

_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)+(0.0292P)²+2.1415P] 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         1640
_refine_ls_number_parameters     134
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0227
_refine_ls_R_factor_gt           0.0209
_refine_ls_wR_factor_ref         0.0542
_refine_ls_wR_factor_gt          0.0534
_refine_ls_goodness_of_fit_ref   1.070
_refine_ls_restrained_S_all      1.070
_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
Zn1 Zn 0.162446(17) 0.124055(15) 0.384591(19) 0.01630(8) Uani 1 1 d . . .
O1 O 0.33274(11) 0.17173(11) 0.47421(13) 0.0222(3) Uani 1 1 d . . .
N1 N 0.45250(12) 0.25251(11) 0.68055(15) 0.0163(3) Uani 1 1 d . . .
N2 N 0.14823(14) -0.06169(12) 0.70238(16) 0.0210(3) Uani 1 1 d . . .
N3 N 0.13879(16) -0.13501(12) 0.60028(18) 0.0247(3) Uani 1 1 d . . .
N4 N 0.13766(15) -0.08518(13) 0.49224(17) 0.0241(3) Uani 1 1 d . . .
N5 N 0.14622(14) 0.02278(12) 0.51871(16) 0.0203(3) Uani 1 1 d . . .
N6 N 0.1699(2) 0.12885(15) 0.7186(2) 0.0342(4) Uani 1 1 d . . .
H3 H 0.163(2) 0.181(2) 0.675(3) 0.028(6) Uiso 1 1 d . . .
H2 H 0.158(3) 0.1289(19) 0.792(3) 0.036(7) Uiso 1 1 d . . .
C1 C 0.41448(15) 0.16294(14) 0.60649(18) 0.0169(3) Uani 1 1 d . . .
C2 C 0.46141(15) 0.06008(14) 0.67573(19) 0.0197(3) Uani 1 1 d . . .
C3 C 0.42634(18) -0.03742(16) 0.6018(2) 0.0274(4) Uani 1 1 d . . .
H1 H 0.375(2) -0.0376(18) 0.497(3) 0.025(6) Uiso 1 1 d . . .
C4 C 0.4640(2) -0.13256(16) 0.6755(3) 0.0367(5) Uani 1 1 d . . .
H0 H 0.446(2) -0.198(2) 0.632(3) 0.043(7) Uiso 1 1 d . . .
C5 C 0.15410(15) 0.03475(14) 0.64959(19) 0.0195(3) 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 N5 1.9632(15) . ?
Zn1 O1 1.9678(14) . ?
Zn1 N2 1.9895(15) 6 ?
Zn1 N1 1.9937(14) 7_556 ?
O1 C1 1.295(2) . ?
N1 C1 1.318(2) . ?
N1 N1 1.393(3) 2_656 ?
N1 Zn1 1.9937(14) 7_556 ?
N2 C5 1.339(2) . ?
N2 N3 1.369(2) . ?
N2 Zn1 1.9895(15) 6_556 ?
N3 N4 1.283(2) . ?
N4 N5 1.369(2) . ?
N5 C5 1.335(2) . ?
N6 C5 1.345(3) . ?
C1 C2 1.458(2) . ?
C2 C3 1.400(3) . ?
C2 C2 1.406(4) 2_656 ?
C3 C4 1.376(3) . ?
C4 C4 1.401(5) 2_656 ?

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
N5 Zn1 O1 106.71(6) . . ?
N5 Zn1 N2 115.99(6) . 6 ?
O1 Zn1 N2 100.70(7) . 6 ?
N5 Zn1 N1 116.96(6) . 7_556 ?
O1 Zn1 N1 111.83(6) . 7_556 ?
N2 Zn1 N1 103.57(6) 6 7_556 ?
C1 O1 Zn1 129.12(12) . . ?
C1 N1 N1 121.30(10) . 2_656 ?
C1 N1 Zn1 116.40(11) . 7_556 ?
N1 N1 Zn1 119.30(8) 2_656 7_556 ?
C5 N2 N3 106.29(14) . . ?
C5 N2 Zn1 138.39(13) . 6_556 ?
N3 N2 Zn1 115.08(11) . 6_556 ?
N4 N3 N2 108.97(15) . . ?
N3 N4 N5 109.24(15) . . ?
C5 N5 N4 106.27(14) . . ?
C5 N5 Zn1 132.52(13) . . ?
N4 N5 Zn1 120.81(12) . . ?
O1 C1 N1 116.93(16) . . ?
O1 C1 C2 123.13(16) . . ?
N1 C1 C2 119.90(15) . . ?
C3 C2 C2 119.66(12) . 2_656 ?
C3 C2 C1 122.43(17) . . ?
C2 C2 C1 117.79(10) 2_656 . ?
C4 C3 C2 119.9(2) . . ?
C3 C4 C4 120.39(14) . 2_656 ?
N5 C5 N2 109.22(16) . . ?
N5 C5 N6 124.92(17) . . ?
N2 C5 N6 125.82(17) . . ?

_diffrn_measured_fraction_theta_max 0.996
_diffrn_reflns_theta_full        27.43
_diffrn_measured_fraction_theta_full 0.996
_refine_diff_density_max         0.564
_refine_diff_density_min         -0.382
_refine_diff_density_rms         0.074
_database_code_depnum_ccdc_archive 'CCDC 953444'
#######################################################################
#
#                 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_4

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C22 H18 N16 O10 Zn5'
_chemical_formula_weight         993.37

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/m

loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y, -z'
'x+1/2, y+1/2, z'
'-x+1/2, y+1/2, -z'
'-x, -y, -z'
'x, -y, z'
'-x+1/2, -y+1/2, -z'
'x+1/2, -y+1/2, z'

_cell_length_a                   18.923(4)
_cell_length_b                   11.121(2)
_cell_length_c                   15.759(3)
_cell_angle_alpha                90.00
_cell_angle_beta                 102.62(3)
_cell_angle_gamma                90.00
_cell_volume                     3236.5(11)
_cell_formula_units_Z            4
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    ?
_cell_measurement_theta_min      ?
_cell_measurement_theta_max      ?

_exptl_crystal_description       block
_exptl_crystal_colour            colorless
_exptl_crystal_size_max          0.12
_exptl_crystal_size_mid          0.10
_exptl_crystal_size_min          0.10
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    2.039
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1968
_exptl_absorpt_coefficient_mu    3.733
_exptl_absorpt_correction_type   empirical
_exptl_absorpt_correction_T_min  0.645
_exptl_absorpt_correction_T_max  0.688
_exptl_absorpt_process_details   Process-auto

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      293(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Rigaku RAXIS-RAPID'
_diffrn_measurement_method       omega-scan
_diffrn_detector_area_resol_mean 10.0
_diffrn_standards_number         0
_diffrn_standards_interval_count 0
_diffrn_standards_interval_time  0
_diffrn_standards_decay_%        0
_diffrn_reflns_number            15933
_diffrn_reflns_av_R_equivalents  0.0463
_diffrn_reflns_av_sigmaI/netI    0.0395
_diffrn_reflns_limit_h_min       -22
_diffrn_reflns_limit_h_max       24
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_theta_min         3.05
_diffrn_reflns_theta_max         27.46
_reflns_number_total             3876
_reflns_number_gt                3390
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       Process-auto
_computing_cell_refinement       Process-auto
_computing_data_reduction        Process-auto
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    ?
_computing_publication_material  ?

_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)+(0.0431P)²+20.5882P] 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         3876
_refine_ls_number_parameters     258
_refine_ls_number_restraints     2
_refine_ls_R_factor_all          0.0505
_refine_ls_R_factor_gt           0.0431
_refine_ls_wR_factor_ref         0.1105
_refine_ls_wR_factor_gt          0.1070
_refine_ls_goodness_of_fit_ref   1.077
_refine_ls_restrained_S_all      1.077
_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
Zn1 Zn 0.76320(3) 0.14401(4) 0.90872(3) 0.02466(13) Uani 1 1 d . . .
Zn2 Zn 0.68795(2) 0.35791(4) 0.54514(3) 0.02253(13) Uani 1 1 d . . .
Zn3 Zn 0.58280(3) 0.5000 0.66639(4) 0.02348(16) Uani 1 2 d S . .
O1 O 0.83303(17) 0.2584(3) 0.97522(18) 0.0302(6) Uani 1 1 d . . .
O2 O 0.83934(17) 0.2582(3) 0.54853(18) 0.0299(6) Uani 1 1 d . . .
O3 O 0.4149(3) 0.5000 0.7929(3) 0.072(2) Uani 1 2 d S . .
O4 O 0.3642(2) 0.5000 0.6172(3) 0.0437(12) Uani 1 2 d S . .
O5 O 0.5259(2) 0.5000 0.7691(3) 0.0366(11) Uani 1 2 d S . .
O6 O 0.4778(2) 0.5000 0.5999(3) 0.0307(9) Uani 1 2 d S . .
OH1 O 0.6236(2) 0.5000 0.5543(2) 0.0208(8) Uani 1 2 d S . .
H00 H 0.595(4) 0.5000 0.512(4) 0.019(16) Uiso 1 2 d S . .
OH2 O 0.8125(3) 0.0000 0.8867(3) 0.0358(11) Uani 1 2 d S . .
H02 H 0.843(4) 0.0000 0.872(5) 0.04(2) Uiso 1 2 d S . .
N1 N 0.68900(19) 0.3002(3) 0.6654(2) 0.0279(7) Uani 1 1 d . . .
N2 N 0.63779(19) 0.3482(3) 0.7100(2) 0.0281(7) Uani 1 1 d . . .
N3 N 0.7117(2) 0.2252(3) 0.8003(2) 0.0311(8) Uani 1 1 d . . .
N4 N 0.6160(3) 0.3189(5) 0.8509(3) 0.0623(15) Uani 1 1 d . . .
H4A H 0.5785 0.3647 0.8405 0.080 Uiso 1 1 calc R . .
H4B H 0.6294 0.2849 0.9008 0.080 Uiso 1 1 calc R . .
N5 N 0.7871(3) 0.1671(6) 0.7056(3) 0.081(2) Uani 1 1 d . . .
H5A H 0.7987 0.1738 0.6560 0.080 Uiso 1 1 calc R . .
H5B H 0.8120 0.1214 0.7451 0.080 Uiso 1 1 calc R . .
N6 N 0.9407(6) 0.2551(5) 0.8817(7) 0.065(3) Uiso 0.50 1 d PD . .
H6A H 0.9732 0.2258 0.8571 0.080 Uiso 0.50 1 calc PR . .
H6B H 0.9163 0.2083 0.9081 0.080 Uiso 0.50 1 calc PR . .
N7 N 0.79737(18) 0.4370(3) 1.0169(2) 0.0248(7) Uani 1 1 d . . .
N8 N 0.9890(5) 0.2577(5) 0.6109(6) 0.056(2) Uiso 0.50 1 d PD . .
H8A H 1.0318 0.2297 0.6304 0.080 Uiso 0.50 1 calc PR . .
H8B H 0.9528 0.2094 0.5971 0.080 Uiso 0.50 1 calc PR . .
N9 N 0.78242(17) 0.4372(3) 0.5390(2) 0.0216(6) Uani 1 1 d . . .
C1 C 0.7305(3) 0.2279(4) 0.7214(3) 0.0349(10) Uani 1 1 d . . .
C2 C 0.6540(2) 0.3002(4) 0.7884(3) 0.0304(9) Uani 1 1 d . . .
C3 C 0.4577(3) 0.5000 0.7450(4) 0.0330(14) Uani 1 2 d S . .
C4 C 0.4286(3) 0.5000 0.6459(4) 0.0268(12) Uani 1 2 d S . .
C5 C 0.9701(4) 0.4386(7) 0.8351(5) 0.085(2) Uani 1 1 d . . .
H5 H 0.9995 0.3977 0.8046 0.080 Uiso 1 1 calc R . .
C6 C 0.9278(4) 0.3746(5) 0.8789(4) 0.0576(16) Uani 1 1 d D . .
C7 C 0.8822(2) 0.4361(4) 0.9229(3) 0.0321(9) Uani 1 1 d . . .
C8 C 0.8358(2) 0.3760(4) 0.9717(2) 0.0250(8) Uani 1 1 d . . .
C9 C 1.0416(3) 0.4373(7) 0.6266(4) 0.079(3) Uani 1 1 d . . .
H9 H 1.0848 0.3952 0.6436 0.080 Uiso 1 1 calc R . .
C10 C 0.9786(3) 0.3774(5) 0.6017(3) 0.0481(13) Uani 1 1 d D . .
C11 C 0.9123(2) 0.4366(4) 0.5755(2) 0.0262(8) Uani 1 1 d . . .
C12 C 0.8428(2) 0.3761(3) 0.5519(2) 0.0216(7) 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 OH2 1.923(3) . ?
Zn1 O1 1.964(3) . ?
Zn1 N3 1.990(4) . ?
Zn1 N7 2.021(3) 7_657 ?
Zn2 O2 1.944(3) 7_656 ?
Zn2 N1 1.997(3) . ?
Zn2 N9 2.015(3) . ?
Zn2 OH1 2.019(2) . ?
Zn3 N2 2.023(4) 6_565 ?
Zn3 N2 2.023(4) . ?
Zn3 O6 2.034(4) . ?
Zn3 OH1 2.076(4) . ?
Zn3 O5 2.132(4) . ?
O1 C8 1.311(5) . ?
O2 C12 1.313(5) . ?
O2 Zn2 1.944(3) 7_656 ?
O3 C3 1.222(7) . ?
O4 C4 1.204(7) . ?
O5 C3 1.262(7) . ?
O6 C4 1.298(7) . ?
OH1 Zn2 2.019(2) 6_565 ?
OH2 Zn1 1.923(3) 6 ?
N1 C1 1.319(5) . ?
N1 N2 1.419(4) . ?
N2 C2 1.319(5) . ?
N3 C2 1.354(5) . ?
N3 C1 1.366(5) . ?
N4 C2 1.355(5) . ?
N5 C1 1.335(6) . ?
N6 C6 1.3495(11) . ?
N7 C8 1.314(5) . ?
N7 N7 1.401(6) 6_565 ?
N7 Zn1 2.021(3) 7_657 ?
N8 C10 1.3484(11) . ?
N9 C12 1.307(5) . ?
N9 N9 1.396(6) 6_565 ?
C3 C4 1.538(8) . ?
C5 C5 1.366(15) 6_565 ?
C5 C6 1.366(8) . ?
C6 C7 1.398(6) . ?
C7 C7 1.421(9) 6_565 ?
C7 C8 1.450(6) . ?
C9 C10 1.347(8) . ?
C9 C9 1.395(16) 6_565 ?
C10 C11 1.397(6) . ?
C11 C11 1.410(9) 6_565 ?
C11 C12 1.451(6) . ?

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
OH2 Zn1 O1 109.83(18) . . ?
OH2 Zn1 N3 112.89(19) . . ?
O1 Zn1 N3 108.08(14) . . ?
OH2 Zn1 N7 95.30(15) . 7_657 ?
O1 Zn1 N7 112.33(13) . 7_657 ?
N3 Zn1 N7 117.85(15) . 7_657 ?
O2 Zn2 N1 116.95(14) 7_656 . ?
O2 Zn2 N9 110.23(13) 7_656 . ?
N1 Zn2 N9 111.18(14) . . ?
O2 Zn2 OH1 120.65(14) 7_656 . ?
N1 Zn2 OH1 93.70(14) . . ?
N9 Zn2 OH1 102.48(12) . . ?
N2 Zn3 N2 113.1(2) 6_565 . ?
N2 Zn3 O6 123.16(11) 6_565 . ?
N2 Zn3 O6 123.16(11) . . ?
N2 Zn3 OH1 91.70(11) 6_565 . ?
N2 Zn3 OH1 91.70(11) . . ?
O6 Zn3 OH1 93.73(16) . . ?
N2 Zn3 O5 92.86(11) 6_565 . ?
N2 Zn3 O5 92.86(11) . . ?
O6 Zn3 O5 77.99(16) . . ?
OH1 Zn3 O5 171.72(16) . . ?
C8 O1 Zn1 130.7(3) . . ?
C12 O2 Zn2 134.1(3) . 7_656 ?
C3 O5 Zn3 115.1(4) . . ?
C4 O6 Zn3 116.8(4) . . ?
Zn2 OH1 Zn2 102.98(16) 6_565 . ?
Zn2 OH1 Zn3 113.77(13) 6_565 . ?
Zn2 OH1 Zn3 113.77(13) . . ?
Zn1 OH2 Zn1 112.8(2) 6 . ?
C1 N1 N2 105.7(3) . . ?
C1 N1 Zn2 135.4(3) . . ?
N2 N1 Zn2 118.9(3) . . ?
C2 N2 N1 105.5(3) . . ?
C2 N2 Zn3 130.7(3) . . ?
N1 N2 Zn3 120.1(2) . . ?
C2 N3 C1 102.9(3) . . ?
C2 N3 Zn1 128.8(3) . . ?
C1 N3 Zn1 128.0(3) . . ?
C8 N7 N7 121.1(2) . 6_565 ?
C8 N7 Zn1 122.4(3) . 7_657 ?
N7 N7 Zn1 116.47(9) 6_565 7_657 ?
C12 N9 N9 121.3(2) . 6_565 ?
C12 N9 Zn2 121.3(3) . . ?
N9 N9 Zn2 115.97(9) 6_565 . ?
N1 C1 N5 124.7(4) . . ?
N1 C1 N3 112.7(4) . . ?
N5 C1 N3 122.5(4) . . ?
N2 C2 N3 113.2(3) . . ?
N2 C2 N4 124.5(4) . . ?
N3 C2 N4 122.2(4) . . ?
O3 C3 O5 125.8(6) . . ?
O3 C3 C4 119.3(6) . . ?
O5 C3 C4 114.9(5) . . ?
O4 C4 O6 125.4(6) . . ?
O4 C4 C3 119.4(5) . . ?
O6 C4 C3 115.2(5) . . ?
C5 C5 C6 121.4(4) 6_565 . ?
N6 C6 C5 114.1(7) . . ?
N6 C6 C7 126.3(7) . . ?
C5 C6 C7 119.3(5) . . ?
C6 C7 C7 119.3(3) . 6_565 ?
C6 C7 C8 123.2(4) . . ?
C7 C7 C8 117.5(2) 6_565 . ?
O1 C8 N7 117.3(4) . . ?
O1 C8 C7 121.2(4) . . ?
N7 C8 C7 121.4(4) . . ?
C10 C9 C9 119.6(4) . 6_565 ?
C9 C10 N8 110.9(6) . . ?
C9 C10 C11 122.2(6) . . ?
N8 C10 C11 126.7(7) . . ?
C10 C11 C11 118.1(3) . 6_565 ?
C10 C11 C12 124.2(4) . . ?
C11 C11 C12 117.6(2) 6_565 . ?
N9 C12 O2 118.6(4) . . ?
N9 C12 C11 120.7(4) . . ?
O2 C12 C11 120.5(4) . . ?

_diffrn_measured_fraction_theta_max 0.994
_diffrn_reflns_theta_full        27.46
_diffrn_measured_fraction_theta_full 0.994
_refine_diff_density_max         0.999
_refine_diff_density_min         -1.114
_refine_diff_density_rms         0.123
_database_code_depnum_ccdc_archive 'CCDC 971308'
