# Supplementary Material (ESI) for CrystEngComm
# This journal is (c) The Royal Society of Chemistry 2010

data_global
_journal_name_full               CrystEngComm

_journal_coden_Cambridge         1350
_journal_volume                  ?
_journal_page_first              ?
_journal_year                    ?

_publ_contact_author_name        'Wang Yaoyu'
_publ_contact_author_email       WYAOYU@NWU.EDU.CN

_publ_section_title              
;
A series of Zn(II) coordination complexes
derived from isomeric phenylenediacetic acid and dipyridyl ligands:
syntheses, crystal structures, and characterizations
;
loop_
_publ_author_name
'Wang Yaoyu.'
'Ai-Yun Fu.'
E.Kh.Lermontova
'Rui-Ting Liu.'
'Qi-Zhen Shi.'
;
G.-P.Yang
;
'Wei-Hong Zhang.'

# Attachment '1.cif'

data_1
_database_code_depnum_ccdc_archive 'CCDC 729341'

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C20 H20 N2 O6 Zn'
_chemical_formula_sum            'C20 H20 N2 O6 Zn'
_chemical_formula_weight         449.75

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'
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'
H H 0.0000 0.0000 '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                   7.378(3)
_cell_length_b                   11.238(5)
_cell_length_c                   11.373(5)
_cell_angle_alpha                90.253(6)
_cell_angle_beta                 94.771(6)
_cell_angle_gamma                105.027(5)
_cell_volume                     907.2(7)
_cell_formula_units_Z            2
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    2545
_cell_measurement_theta_min      2.564
_cell_measurement_theta_max      27.516

_exptl_crystal_description       block
_exptl_crystal_colour            colorless
_exptl_crystal_size_max          0.31
_exptl_crystal_size_mid          0.11
_exptl_crystal_size_min          0.01
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.646
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             464
_exptl_absorpt_coefficient_mu    1.397
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.6713
_exptl_absorpt_correction_T_max  0.9862
_exptl_absorpt_process_details   sadabs

_exptl_special_details           
;
?
;

_diffrn_ambient_temperature      296(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  ?
_diffrn_measurement_method       ?
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            4306
_diffrn_reflns_av_R_equivalents  0.0245
_diffrn_reflns_av_sigmaI/netI    0.0505
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_theta_min         1.80
_diffrn_reflns_theta_max         25.00
_reflns_number_total             3049
_reflns_number_gt                2702
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_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)+(0.1769P)²+24.4515P] 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         3049
_refine_ls_number_parameters     274
_refine_ls_number_restraints     6
_refine_ls_R_factor_all          0.1053
_refine_ls_R_factor_gt           0.1002
_refine_ls_wR_factor_ref         0.3431
_refine_ls_wR_factor_gt          0.3411
_refine_ls_goodness_of_fit_ref   1.053
_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 0.75326(17) 0.25032(11) 0.32264(10) 0.0227(5) Uani 1 1 d . . .
O1 O 0.7704(11) 0.0678(7) 0.3311(7) 0.0287(17) Uani 1 1 d . . .
O2 O 1.0767(14) 0.0828(9) 0.3483(12) 0.059(3) Uani 1 1 d . . .
O3 O 0.4378(14) -0.5792(9) 0.2989(12) 0.058(3) Uani 1 1 d . . .
O4 O 0.7427(11) -0.5658(7) 0.3233(7) 0.0274(17) Uani 1 1 d . . .
O5 O 0.4539(11) 0.1864(7) 0.2976(9) 0.036(2) Uani 1 1 d D . .
O6 O 1.0526(11) 0.3129(7) 0.3459(9) 0.035(2) Uani 1 1 d D . .
N1 N 0.7384(14) 0.2535(8) 0.5091(8) 0.028(2) Uani 1 1 d . . .
N2 N 0.7572(14) 0.2491(9) 1.1344(8) 0.029(2) Uani 1 1 d . . .
C1 C 0.9096(16) 0.0234(11) 0.3425(11) 0.031(3) Uani 1 1 d . . .
C2 C 0.8658(17) -0.1185(10) 0.3509(10) 0.029(2) Uani 1 1 d . . .
H2A H 0.9773 -0.1402 0.3853 0.034 Uiso 1 1 calc R . .
H2B H 0.7669 -0.1462 0.4033 0.034 Uiso 1 1 calc R . .
C3 C 0.8039(16) -0.1861(10) 0.2311(11) 0.028(2) Uani 1 1 d . . .
C4 C 0.8529(19) -0.1255(12) 0.1267(12) 0.038(3) Uani 1 1 d . . .
H4 H 0.9215 -0.0433 0.1305 0.046 Uiso 1 1 calc R . .
C5 C 0.802(2) -0.1852(12) 0.0189(11) 0.039(3) Uani 1 1 d . . .
H5A H 0.8365 -0.1433 -0.0494 0.047 Uiso 1 1 calc R . .
C6 C 0.699(2) -0.3072(13) 0.0110(11) 0.042(3) Uani 1 1 d . . .
H6A H 0.6606 -0.3472 -0.0621 0.050 Uiso 1 1 calc R . .
C7 C 0.6529(18) -0.3688(11) 0.1143(12) 0.036(3) Uani 1 1 d . . .
H7 H 0.5865 -0.4515 0.1094 0.043 Uiso 1 1 calc R . .
C8 C 0.7036(15) -0.3107(10) 0.2251(10) 0.025(2) Uani 1 1 d . . .
C9 C 0.6488(16) -0.3808(10) 0.3381(11) 0.029(2) Uani 1 1 d . . .
H9A H 0.5394 -0.3596 0.3648 0.035 Uiso 1 1 calc R . .
H9B H 0.7514 -0.3544 0.3993 0.035 Uiso 1 1 calc R . .
C10 C 0.6041(16) -0.5215(11) 0.3207(11) 0.031(3) Uani 1 1 d . . .
C11 C 0.6304(17) 0.1600(11) 0.5661(10) 0.029(2) Uani 1 1 d . . .
H11 H 0.5509 0.0952 0.5207 0.035 Uiso 1 1 calc R . .
C12 C 0.6295(16) 0.1536(10) 0.6870(10) 0.028(2) Uani 1 1 d . . .
H12 H 0.5523 0.0860 0.7208 0.033 Uiso 1 1 calc R . .
C13 C 0.7456(16) 0.2497(11) 0.7583(10) 0.029(2) Uani 1 1 d . . .
C14 C 0.8548(16) 0.3483(10) 0.6988(10) 0.028(2) Uani 1 1 d . . .
H14 H 0.9326 0.4157 0.7417 0.033 Uiso 1 1 calc R . .
C15 C 0.8476(16) 0.3463(10) 0.5777(9) 0.027(2) Uani 1 1 d . . .
H15 H 0.9226 0.4130 0.5413 0.032 Uiso 1 1 calc R . .
C16 C 0.7488(16) 0.2486(11) 0.8883(10) 0.029(2) Uani 1 1 d . . .
C17 C 0.7000(18) 0.1398(11) 0.9480(10) 0.033(3) Uani 1 1 d . . .
H17 H 0.6633 0.0645 0.9069 0.040 Uiso 1 1 calc R . .
C18 C 0.7065(18) 0.1446(12) 1.0705(10) 0.034(3) Uani 1 1 d . . .
H18 H 0.6736 0.0707 1.1098 0.041 Uiso 1 1 calc R . .
C19 C 0.8041(17) 0.3542(11) 1.0761(10) 0.031(3) Uani 1 1 d . . .
H19 H 0.8397 0.4283 1.1194 0.037 Uiso 1 1 calc R . .
C20 C 0.8020(18) 0.3578(11) 0.9546(10) 0.032(3) Uani 1 1 d . . .
H20 H 0.8362 0.4329 0.9176 0.039 Uiso 1 1 calc R . .
H5C H 0.357(8) 0.132(7) 0.304(12) 0.039 Uiso 1 1 d D . .
H5D H 0.430(14) 0.249(6) 0.270(12) 0.039 Uiso 1 1 d D . .
H6C H 1.152(8) 0.365(7) 0.341(12) 0.039 Uiso 1 1 d D . .
H6D H 1.073(14) 0.248(6) 0.369(12) 0.039 Uiso 1 1 d 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 O4 2.088(7) 1_565 ?
Zn1 O1 2.090(8) . ?
Zn1 O6 2.130(8) . ?
Zn1 O5 2.132(8) . ?
Zn1 N1 2.133(9) . ?
Zn1 N2 2.143(9) 1_554 ?
O1 C1 1.250(14) . ?
O2 C1 1.237(15) . ?
O3 C10 1.234(15) . ?
O4 C10 1.247(14) . ?
O4 Zn1 2.088(7) 1_545 ?
O5 H5C 0.819(10) . ?
O5 H5D 0.819(10) . ?
O6 H6C 0.822(11) . ?
O6 H6D 0.82(9) . ?
N1 C15 1.342(14) . ?
N1 C11 1.348(15) . ?
N2 C18 1.330(16) . ?
N2 C19 1.337(15) . ?
N2 Zn1 2.143(9) 1_556 ?
C1 C2 1.548(16) . ?
C2 C3 1.532(16) . ?
C2 H2A 0.9700 . ?
C2 H2B 0.9700 . ?
C3 C4 1.398(18) . ?
C3 C8 1.402(15) . ?
C4 C5 1.371(18) . ?
C4 H4 0.9300 . ?
C5 C6 1.384(19) . ?
C5 H5A 0.9300 . ?
C6 C7 1.387(19) . ?
C6 H6A 0.9300 . ?
C7 C8 1.394(17) . ?
C7 H7 0.9300 . ?
C8 C9 1.538(16) . ?
C9 C10 1.537(16) . ?
C9 H9A 0.9700 . ?
C9 H9B 0.9700 . ?
C11 C12 1.377(16) . ?
C11 H11 0.9300 . ?
C12 C13 1.398(16) . ?
C12 H12 0.9300 . ?
C13 C14 1.404(16) . ?
C13 C16 1.476(16) . ?
C14 C15 1.373(16) . ?
C14 H14 0.9300 . ?
C15 H15 0.9300 . ?
C16 C17 1.381(17) . ?
C16 C20 1.386(17) . ?
C17 C18 1.390(17) . ?
C17 H17 0.9300 . ?
C18 H18 0.9300 . ?
C19 C20 1.382(16) . ?
C19 H19 0.9300 . ?
C20 H20 0.9300 . ?

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
O4 Zn1 O1 177.0(3) 1_565 . ?
O4 Zn1 O6 88.5(3) 1_565 . ?
O1 Zn1 O6 90.1(3) . . ?
O4 Zn1 O5 91.8(3) 1_565 . ?
O1 Zn1 O5 89.6(3) . . ?
O6 Zn1 O5 179.3(4) . . ?
O4 Zn1 N1 88.1(3) 1_565 . ?
O1 Zn1 N1 89.3(3) . . ?
O6 Zn1 N1 90.6(4) . . ?
O5 Zn1 N1 89.9(4) . . ?
O4 Zn1 N2 90.7(3) 1_565 1_554 ?
O1 Zn1 N2 92.0(3) . 1_554 ?
O6 Zn1 N2 91.4(4) . 1_554 ?
O5 Zn1 N2 88.1(4) . 1_554 ?
N1 Zn1 N2 177.6(4) . 1_554 ?
C1 O1 Zn1 131.2(7) . . ?
C10 O4 Zn1 129.8(7) . 1_545 ?
Zn1 O5 H5C 150(7) . . ?
Zn1 O5 H5D 99(7) . . ?
H5C O5 H5D 111(2) . . ?
Zn1 O6 H6C 152(7) . . ?
Zn1 O6 H6D 98(7) . . ?
H6C O6 H6D 110.4(19) . . ?
C15 N1 C11 115.8(10) . . ?
C15 N1 Zn1 121.2(7) . . ?
C11 N1 Zn1 122.8(8) . . ?
C18 N2 C19 117.3(10) . . ?
C18 N2 Zn1 121.6(8) . 1_556 ?
C19 N2 Zn1 121.1(8) . 1_556 ?
O2 C1 O1 125.8(12) . . ?
O2 C1 C2 118.0(11) . . ?
O1 C1 C2 116.2(10) . . ?
C3 C2 C1 113.2(9) . . ?
C3 C2 H2A 108.9 . . ?
C1 C2 H2A 108.9 . . ?
C3 C2 H2B 108.9 . . ?
C1 C2 H2B 108.9 . . ?
H2A C2 H2B 107.7 . . ?
C4 C3 C8 119.2(11) . . ?
C4 C3 C2 120.3(10) . . ?
C8 C3 C2 120.4(10) . . ?
C5 C4 C3 121.1(12) . . ?
C5 C4 H4 119.4 . . ?
C3 C4 H4 119.4 . . ?
C4 C5 C6 120.5(12) . . ?
C4 C5 H5A 119.7 . . ?
C6 C5 H5A 119.7 . . ?
C5 C6 C7 118.7(12) . . ?
C5 C6 H6A 120.6 . . ?
C7 C6 H6A 120.6 . . ?
C6 C7 C8 122.0(12) . . ?
C6 C7 H7 119.0 . . ?
C8 C7 H7 119.0 . . ?
C7 C8 C3 118.4(11) . . ?
C7 C8 C9 120.9(10) . . ?
C3 C8 C9 120.7(10) . . ?
C8 C9 C10 113.2(9) . . ?
C8 C9 H9A 108.9 . . ?
C10 C9 H9A 108.9 . . ?
C8 C9 H9B 108.9 . . ?
C10 C9 H9B 108.9 . . ?
H9A C9 H9B 107.8 . . ?
O3 C10 O4 125.9(11) . . ?
O3 C10 C9 118.1(11) . . ?
O4 C10 C9 115.9(10) . . ?
N1 C11 C12 124.5(11) . . ?
N1 C11 H11 117.7 . . ?
C12 C11 H11 117.7 . . ?
C11 C12 C13 119.5(11) . . ?
C11 C12 H12 120.3 . . ?
C13 C12 H12 120.3 . . ?
C12 C13 C14 115.9(10) . . ?
C12 C13 C16 121.9(10) . . ?
C14 C13 C16 122.2(11) . . ?
C15 C14 C13 120.6(10) . . ?
C15 C14 H14 119.7 . . ?
C13 C14 H14 119.7 . . ?
N1 C15 C14 123.6(10) . . ?
N1 C15 H15 118.2 . . ?
C14 C15 H15 118.2 . . ?
C17 C16 C20 117.7(11) . . ?
C17 C16 C13 121.6(11) . . ?
C20 C16 C13 120.8(11) . . ?
C16 C17 C18 119.0(11) . . ?
C16 C17 H17 120.5 . . ?
C18 C17 H17 120.5 . . ?
N2 C18 C17 123.5(11) . . ?
N2 C18 H18 118.2 . . ?
C17 C18 H18 118.2 . . ?
N2 C19 C20 123.0(11) . . ?
N2 C19 H19 118.5 . . ?
C20 C19 H19 118.5 . . ?
C19 C20 C16 119.6(11) . . ?
C19 C20 H20 120.2 . . ?
C16 C20 H20 120.2 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
O4 Zn1 O1 C1 -64(6) 1_565 . . . ?
O6 Zn1 O1 C1 -1.5(10) . . . . ?
O5 Zn1 O1 C1 177.9(10) . . . . ?
N1 Zn1 O1 C1 -92.2(10) . . . . ?
N2 Zn1 O1 C1 89.9(10) 1_554 . . . ?
O4 Zn1 N1 C15 -46.9(9) 1_565 . . . ?
O1 Zn1 N1 C15 131.7(9) . . . . ?
O6 Zn1 N1 C15 41.6(9) . . . . ?
O5 Zn1 N1 C15 -138.7(9) . . . . ?
N2 Zn1 N1 C15 -106(8) 1_554 . . . ?
O4 Zn1 N1 C11 137.8(10) 1_565 . . . ?
O1 Zn1 N1 C11 -43.6(9) . . . . ?
O6 Zn1 N1 C11 -133.7(9) . . . . ?
O5 Zn1 N1 C11 46.0(9) . . . . ?
N2 Zn1 N1 C11 79(9) 1_554 . . . ?
Zn1 O1 C1 O2 -2(2) . . . . ?
Zn1 O1 C1 C2 177.3(7) . . . . ?
O2 C1 C2 C3 -102.8(14) . . . . ?
O1 C1 C2 C3 77.6(13) . . . . ?
C1 C2 C3 C4 22.7(15) . . . . ?
C1 C2 C3 C8 -159.7(10) . . . . ?
C8 C3 C4 C5 1.2(19) . . . . ?
C2 C3 C4 C5 178.8(12) . . . . ?
C3 C4 C5 C6 0(2) . . . . ?
C4 C5 C6 C7 -2(2) . . . . ?
C5 C6 C7 C8 2(2) . . . . ?
C6 C7 C8 C3 -0.1(18) . . . . ?
C6 C7 C8 C9 179.2(12) . . . . ?
C4 C3 C8 C7 -1.3(17) . . . . ?
C2 C3 C8 C7 -179.0(10) . . . . ?
C4 C3 C8 C9 179.4(11) . . . . ?
C2 C3 C8 C9 1.8(16) . . . . ?
C7 C8 C9 C10 20.9(15) . . . . ?
C3 C8 C9 C10 -159.8(10) . . . . ?
Zn1 O4 C10 O3 -12(2) 1_545 . . . ?
Zn1 O4 C10 C9 172.5(7) 1_545 . . . ?
C8 C9 C10 O3 -95.4(14) . . . . ?
C8 C9 C10 O4 80.5(13) . . . . ?
C15 N1 C11 C12 -1.5(18) . . . . ?
Zn1 N1 C11 C12 174.0(9) . . . . ?
N1 C11 C12 C13 0.6(19) . . . . ?
C11 C12 C13 C14 0.9(17) . . . . ?
C11 C12 C13 C16 179.2(11) . . . . ?
C12 C13 C14 C15 -1.4(17) . . . . ?
C16 C13 C14 C15 -179.7(11) . . . . ?
C11 N1 C15 C14 1.0(17) . . . . ?
Zn1 N1 C15 C14 -174.7(9) . . . . ?
C13 C14 C15 N1 0.5(19) . . . . ?
C12 C13 C16 C17 25.5(18) . . . . ?
C14 C13 C16 C17 -156.2(12) . . . . ?
C12 C13 C16 C20 -154.8(12) . . . . ?
C14 C13 C16 C20 23.5(18) . . . . ?
C20 C16 C17 C18 0.0(18) . . . . ?
C13 C16 C17 C18 179.7(11) . . . . ?
C19 N2 C18 C17 -0.1(19) . . . . ?
Zn1 N2 C18 C17 177.4(10) 1_556 . . . ?
C16 C17 C18 N2 0(2) . . . . ?
C18 N2 C19 C20 -0.2(18) . . . . ?
Zn1 N2 C19 C20 -177.6(9) 1_556 . . . ?
N2 C19 C20 C16 0.3(19) . . . . ?
C17 C16 C20 C19 -0.2(18) . . . . ?
C13 C16 C20 C19 -179.9(11) . . . . ?

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
O5 H5C O2 0.819(10) 2.10(7) 2.833(13) 148(11) 1_455
O5 H5D O3 0.819(10) 1.95(8) 2.667(12) 146(13) 1_565
O6 H6C O3 0.822(11) 2.13(6) 2.882(13) 152(11) 1_665
O6 H6D O2 0.82(9) 1.88(6) 2.638(12) 154(13) .

_diffrn_measured_fraction_theta_max 0.954
_diffrn_reflns_theta_full        25.00
_diffrn_measured_fraction_theta_full 0.954
_refine_diff_density_max         2.283
_refine_diff_density_min         -1.310
_refine_diff_density_rms         0.217

# Attachment '4.cif'

data_4
_database_code_depnum_ccdc_archive 'CCDC 729342'

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C22 H24 N2 O7 Zn'
_chemical_formula_sum            'C22 H24 N2 O7 Zn'
_chemical_formula_weight         493.80

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'
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'
H H 0.0000 0.0000 '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                   6.2047(7)
_cell_length_b                   17.746(2)
_cell_length_c                   20.4535(19)
_cell_angle_alpha                90.00
_cell_angle_beta                 99.009(3)
_cell_angle_gamma                90.00
_cell_volume                     2224.3(4)
_cell_formula_units_Z            4
_cell_measurement_temperature    273(2)
_cell_measurement_reflns_used    771
_cell_measurement_theta_min      2.296
_cell_measurement_theta_max      16.576

_exptl_crystal_description       block
_exptl_crystal_colour            colorless
_exptl_crystal_size_max          0.37
_exptl_crystal_size_mid          0.21
_exptl_crystal_size_min          0.13
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.475
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1024
_exptl_absorpt_coefficient_mu    1.150
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.6756
_exptl_absorpt_correction_T_max  0.8649
_exptl_absorpt_process_details   sadabs

_exptl_special_details           
;
?
;

_diffrn_ambient_temperature      273(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  ?
_diffrn_measurement_method       ?
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            11176
_diffrn_reflns_av_R_equivalents  0.0667
_diffrn_reflns_av_sigmaI/netI    0.0989
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_k_min       -19
_diffrn_reflns_limit_k_max       21
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_limit_l_max       24
_diffrn_reflns_theta_min         1.53
_diffrn_reflns_theta_max         25.09
_reflns_number_total             3960
_reflns_number_gt                1966
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_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)+(0.0432P)²+0.0000P] 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         3960
_refine_ls_number_parameters     289
_refine_ls_number_restraints     6
_refine_ls_R_factor_all          0.1048
_refine_ls_R_factor_gt           0.0460
_refine_ls_wR_factor_ref         0.1225
_refine_ls_wR_factor_gt          0.0925
_refine_ls_goodness_of_fit_ref   1.074
_refine_ls_restrained_S_all      1.090
_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 0.06871(9) 0.48620(3) 0.28062(3) 0.0437(2) Uani 1 1 d . . .
O1 O 0.0621(6) 0.3537(2) 0.3190(2) 0.0844(11) Uani 1 1 d U . .
O2 O -0.1838(6) 0.4155(2) 0.25716(18) 0.0622(11) Uani 1 1 d . . .
O3 O 0.1686(6) 0.1201(2) 0.30285(19) 0.0686(11) Uani 1 1 d . . .
O4 O 0.0485(6) 0.08406(19) 0.20091(18) 0.0583(10) Uani 1 1 d . . .
O5 O 0.9642(6) 0.1488(2) 0.4182(2) 0.0874(13) Uani 1 1 d . . .
H5C H 0.8376 0.1635 0.4099 0.105 Uiso 1 1 d R . .
H5D H 1.0226 0.1411 0.3856 0.105 Uiso 1 1 d R . .
O6 O 0.5227(7) 0.2011(2) 0.3873(2) 0.1062(16) Uani 1 1 d . . .
H6C H 0.4249 0.1783 0.3637 0.127 Uiso 1 1 d R . .
H6D H 0.4312 0.2255 0.4032 0.127 Uiso 1 1 d R . .
O7 O 0.2029(7) 0.2863(2) 0.4434(2) 0.0978(15) Uani 1 1 d . . .
H7C H 0.1358 0.2466 0.4359 0.117 Uiso 1 1 d R . .
H7D H 0.1618 0.3062 0.4074 0.117 Uiso 1 1 d R . .
N1 N 0.1918(6) 0.4767(2) 0.19400(19) 0.0411(10) Uani 1 1 d . . .
N2 N 0.3391(6) 0.4959(2) 0.35185(18) 0.0425(10) Uani 1 1 d . . .
C1 C -0.1109(10) 0.3547(4) 0.2805(3) 0.0721(13) Uani 1 1 d U . .
C2 C -0.2269(8) 0.2829(3) 0.2588(2) 0.0520(14) Uani 1 1 d . . .
H2A H -0.3779 0.2860 0.2655 0.062 Uiso 1 1 calc R . .
H2B H -0.1587 0.2412 0.2848 0.062 Uiso 1 1 calc R . .
C3 C -0.2160(8) 0.2700(3) 0.1857(3) 0.0439(13) Uani 1 1 d . . .
C4 C -0.3878(9) 0.2941(3) 0.1388(3) 0.0554(15) Uani 1 1 d . . .
H4 H -0.5085 0.3164 0.1526 0.067 Uiso 1 1 calc R . .
C5 C -0.3839(10) 0.2857(3) 0.0733(3) 0.0640(17) Uani 1 1 d . . .
H5 H -0.5029 0.3008 0.0426 0.077 Uiso 1 1 calc R . .
C6 C -0.2047(11) 0.2551(3) 0.0522(3) 0.0686(17) Uani 1 1 d . . .
H6 H -0.1994 0.2506 0.0072 0.082 Uiso 1 1 calc R . .
C7 C -0.0303(10) 0.2307(3) 0.0985(3) 0.0613(16) Uani 1 1 d . . .
H7 H 0.0900 0.2091 0.0838 0.074 Uiso 1 1 calc R . .
C8 C -0.0309(8) 0.2378(3) 0.1662(3) 0.0458(13) Uani 1 1 d . . .
C9 C 0.1619(8) 0.2099(3) 0.2151(3) 0.0518(14) Uani 1 1 d . . .
H9A H 0.2894 0.2073 0.1932 0.062 Uiso 1 1 calc R . .
H9B H 0.1924 0.2458 0.2511 0.062 Uiso 1 1 calc R . .
C10 C 0.1229(8) 0.1329(3) 0.2435(3) 0.0469(14) Uani 1 1 d . . .
C11 C 0.3860(8) 0.5063(3) 0.1867(2) 0.0460(13) Uani 1 1 d . . .
H11 H 0.4721 0.5268 0.2237 0.055 Uiso 1 1 calc R . .
C12 C 0.4636(8) 0.5078(3) 0.1280(2) 0.0465(13) Uani 1 1 d . . .
H12 H 0.5986 0.5297 0.1259 0.056 Uiso 1 1 calc R . .
C13 C 0.3454(8) 0.4776(3) 0.0720(2) 0.0420(12) Uani 1 1 d . . .
C14 C 0.1482(8) 0.4449(3) 0.0789(2) 0.0480(13) Uani 1 1 d . . .
H14 H 0.0636 0.4225 0.0426 0.058 Uiso 1 1 calc R . .
C15 C 0.0764(8) 0.4452(3) 0.1388(3) 0.0469(13) Uani 1 1 d . . .
H15 H -0.0573 0.4230 0.1418 0.056 Uiso 1 1 calc R . .
C16 C 0.4164(8) 0.4797(3) 0.0076(2) 0.0507(13) Uani 1 1 d . . .
H16 H 0.3393 0.4504 -0.0258 0.061 Uiso 1 1 calc R . .
C17 C 0.4814(8) 0.4393(3) 0.3659(3) 0.0554(15) Uani 1 1 d . . .
H17 H 0.4514 0.3936 0.3441 0.066 Uiso 1 1 calc R . .
C18 C 0.6689(8) 0.4454(3) 0.4108(3) 0.0560(15) Uani 1 1 d . . .
H18 H 0.7626 0.4044 0.4188 0.067 Uiso 1 1 calc R . .
C19 C 0.7201(8) 0.5130(3) 0.4446(2) 0.0477(13) Uani 1 1 d . . .
C20 C 0.5722(8) 0.5708(3) 0.4306(3) 0.0521(14) Uani 1 1 d . . .
H20 H 0.5973 0.6168 0.4523 0.062 Uiso 1 1 calc R . .
C21 C 0.3883(8) 0.5607(3) 0.3849(3) 0.0525(14) Uani 1 1 d . . .
H21 H 0.2920 0.6010 0.3762 0.063 Uiso 1 1 calc R . .
C22 C 0.9198(8) 0.5243(3) 0.4922(2) 0.0532(15) Uani 1 1 d . . .
H22 H 0.9349 0.5706 0.5137 0.064 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
Zn1 O4 1.943(3) 2 ?
Zn1 O2 2.006(4) . ?
Zn1 N1 2.043(4) . ?
Zn1 N2 2.050(4) . ?
Zn1 O1 2.482(4) . ?
O1 C1 1.228(6) . ?
O2 C1 1.236(7) . ?
O3 C10 1.224(6) . ?
O4 C10 1.263(6) . ?
O4 Zn1 1.943(3) 2_545 ?
O5 H5C 0.8200 . ?
O5 H5D 0.8201 . ?
O6 H6C 0.8200 . ?
O6 H6D 0.8201 . ?
O7 H7C 0.8200 . ?
O7 H7D 0.8201 . ?
N1 C11 1.345(6) . ?
N1 C15 1.359(6) . ?
N2 C17 1.339(6) . ?
N2 C21 1.345(6) . ?
C1 C2 1.496(8) . ?
C2 C3 1.523(6) . ?
C2 H2A 0.9700 . ?
C2 H2B 0.9700 . ?
C3 C4 1.386(7) . ?
C3 C8 1.396(6) . ?
C4 C5 1.352(7) . ?
C4 H4 0.9300 . ?
C5 C6 1.367(7) . ?
C5 H5 0.9300 . ?
C6 C7 1.391(7) . ?
C6 H6 0.9300 . ?
C7 C8 1.391(7) . ?
C7 H7 0.9300 . ?
C8 C9 1.518(6) . ?
C9 C10 1.518(7) . ?
C9 H9A 0.9700 . ?
C9 H9B 0.9700 . ?
C11 C12 1.362(6) . ?
C11 H11 0.9300 . ?
C12 C13 1.369(6) . ?
C12 H12 0.9300 . ?
C13 C14 1.381(6) . ?
C13 C16 1.453(6) . ?
C14 C15 1.366(6) . ?
C14 H14 0.9300 . ?
C15 H15 0.9300 . ?
C16 C16 1.338(9) 3_665 ?
C16 H16 0.9300 . ?
C17 C18 1.369(6) . ?
C17 H17 0.9300 . ?
C18 C19 1.396(7) . ?
C18 H18 0.9300 . ?
C19 C20 1.377(6) . ?
C19 C22 1.464(7) . ?
C20 C21 1.369(6) . ?
C20 H20 0.9300 . ?
C21 H21 0.9300 . ?
C22 C22 1.317(9) 3_766 ?
C22 H22 0.9300 . ?

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
O4 Zn1 O2 107.69(15) 2 . ?
O4 Zn1 N1 116.40(15) 2 . ?
O2 Zn1 N1 97.17(15) . . ?
O4 Zn1 N2 94.37(16) 2 . ?
O2 Zn1 N2 138.10(16) . . ?
N1 Zn1 N2 104.35(15) . . ?
O4 Zn1 O1 139.52(15) 2 . ?
O2 Zn1 O1 55.38(14) . . ?
N1 Zn1 O1 102.87(14) . . ?
N2 Zn1 O1 84.67(14) . . ?
C1 O1 Zn1 80.7(4) . . ?
C1 O2 Zn1 103.2(4) . . ?
C10 O4 Zn1 125.9(4) . 2_545 ?
H5C O5 H5D 114.5 . . ?
H6C O6 H6D 89.9 . . ?
H7C O7 H7D 97.2 . . ?
C11 N1 C15 115.6(4) . . ?
C11 N1 Zn1 121.9(3) . . ?
C15 N1 Zn1 122.4(3) . . ?
C17 N2 C21 116.4(4) . . ?
C17 N2 Zn1 121.9(3) . . ?
C21 N2 Zn1 121.7(3) . . ?
O1 C1 O2 119.5(6) . . ?
O1 C1 C2 120.6(6) . . ?
O2 C1 C2 119.8(6) . . ?
C1 C2 C3 109.1(4) . . ?
C1 C2 H2A 109.9 . . ?
C3 C2 H2A 109.9 . . ?
C1 C2 H2B 109.9 . . ?
C3 C2 H2B 109.9 . . ?
H2A C2 H2B 108.3 . . ?
C4 C3 C8 120.4(5) . . ?
C4 C3 C2 119.0(5) . . ?
C8 C3 C2 120.5(5) . . ?
C5 C4 C3 121.5(6) . . ?
C5 C4 H4 119.3 . . ?
C3 C4 H4 119.3 . . ?
C4 C5 C6 119.8(6) . . ?
C4 C5 H5 120.1 . . ?
C6 C5 H5 120.1 . . ?
C5 C6 C7 119.6(6) . . ?
C5 C6 H6 120.2 . . ?
C7 C6 H6 120.2 . . ?
C6 C7 C8 121.8(5) . . ?
C6 C7 H7 119.1 . . ?
C8 C7 H7 119.1 . . ?
C7 C8 C3 116.9(5) . . ?
C7 C8 C9 120.1(5) . . ?
C3 C8 C9 122.9(5) . . ?
C10 C9 C8 112.9(4) . . ?
C10 C9 H9A 109.0 . . ?
C8 C9 H9A 109.0 . . ?
C10 C9 H9B 109.0 . . ?
C8 C9 H9B 109.0 . . ?
H9A C9 H9B 107.8 . . ?
O3 C10 O4 124.0(5) . . ?
O3 C10 C9 121.3(5) . . ?
O4 C10 C9 114.7(5) . . ?
N1 C11 C12 123.6(5) . . ?
N1 C11 H11 118.2 . . ?
C12 C11 H11 118.2 . . ?
C11 C12 C13 120.8(4) . . ?
C11 C12 H12 119.6 . . ?
C13 C12 H12 119.6 . . ?
C12 C13 C14 116.5(5) . . ?
C12 C13 C16 123.3(5) . . ?
C14 C13 C16 120.2(5) . . ?
C15 C14 C13 120.6(5) . . ?
C15 C14 H14 119.7 . . ?
C13 C14 H14 119.7 . . ?
N1 C15 C14 122.9(4) . . ?
N1 C15 H15 118.5 . . ?
C14 C15 H15 118.5 . . ?
C16 C16 C13 125.5(6) 3_665 . ?
C16 C16 H16 117.2 3_665 . ?
C13 C16 H16 117.2 . . ?
N2 C17 C18 123.1(5) . . ?
N2 C17 H17 118.4 . . ?
C18 C17 H17 118.4 . . ?
C17 C18 C19 120.3(5) . . ?
C17 C18 H18 119.8 . . ?
C19 C18 H18 119.8 . . ?
C20 C19 C18 116.4(5) . . ?
C20 C19 C22 120.2(5) . . ?
C18 C19 C22 123.4(5) . . ?
C21 C20 C19 120.1(5) . . ?
C21 C20 H20 120.0 . . ?
C19 C20 H20 120.0 . . ?
N2 C21 C20 123.7(5) . . ?
N2 C21 H21 118.2 . . ?
C20 C21 H21 118.2 . . ?
C22 C22 C19 126.9(7) 3_766 . ?
C22 C22 H22 116.6 3_766 . ?
C19 C22 H22 116.6 . . ?

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
O4 Zn1 O1 C1 82.5(4) 2 . . . ?
O2 Zn1 O1 C1 6.4(4) . . . . ?
N1 Zn1 O1 C1 -83.4(4) . . . . ?
N2 Zn1 O1 C1 173.0(4) . . . . ?
O4 Zn1 O2 C1 -145.1(4) 2 . . . ?
N1 Zn1 O2 C1 94.2(4) . . . . ?
N2 Zn1 O2 C1 -26.7(5) . . . . ?
O1 Zn1 O2 C1 -6.5(4) . . . . ?
O4 Zn1 N1 C11 75.3(4) 2 . . . ?
O2 Zn1 N1 C11 -170.8(4) . . . . ?
N2 Zn1 N1 C11 -27.1(4) . . . . ?
O1 Zn1 N1 C11 -114.8(3) . . . . ?
O4 Zn1 N1 C15 -99.6(4) 2 . . . ?
O2 Zn1 N1 C15 14.2(4) . . . . ?
N2 Zn1 N1 C15 158.0(3) . . . . ?
O1 Zn1 N1 C15 70.3(4) . . . . ?
O4 Zn1 N2 C17 175.0(4) 2 . . . ?
O2 Zn1 N2 C17 52.2(4) . . . . ?
N1 Zn1 N2 C17 -66.3(4) . . . . ?
O1 Zn1 N2 C17 35.6(4) . . . . ?
O4 Zn1 N2 C21 -8.0(4) 2 . . . ?
O2 Zn1 N2 C21 -130.8(4) . . . . ?
N1 Zn1 N2 C21 110.6(4) . . . . ?
O1 Zn1 N2 C21 -147.4(4) . . . . ?
Zn1 O1 C1 O2 -9.9(6) . . . . ?
Zn1 O1 C1 C2 166.4(6) . . . . ?
Zn1 O2 C1 O1 12.5(7) . . . . ?
Zn1 O2 C1 C2 -163.9(4) . . . . ?
O1 C1 C2 C3 -110.9(6) . . . . ?
O2 C1 C2 C3 65.4(7) . . . . ?
C1 C2 C3 C4 -94.6(6) . . . . ?
C1 C2 C3 C8 82.1(6) . . . . ?
C8 C3 C4 C5 1.5(7) . . . . ?
C2 C3 C4 C5 178.2(5) . . . . ?
C3 C4 C5 C6 -2.0(8) . . . . ?
C4 C5 C6 C7 1.9(8) . . . . ?
C5 C6 C7 C8 -1.2(8) . . . . ?
C6 C7 C8 C3 0.6(7) . . . . ?
C6 C7 C8 C9 179.5(5) . . . . ?
C4 C3 C8 C7 -0.8(7) . . . . ?
C2 C3 C8 C7 -177.4(4) . . . . ?
C4 C3 C8 C9 -179.5(4) . . . . ?
C2 C3 C8 C9 3.8(7) . . . . ?
C7 C8 C9 C10 -99.3(6) . . . . ?
C3 C8 C9 C10 79.5(6) . . . . ?
Zn1 O4 C10 O3 14.0(7) 2_545 . . . ?
Zn1 O4 C10 C9 -168.4(3) 2_545 . . . ?
C8 C9 C10 O3 -134.2(5) . . . . ?
C8 C9 C10 O4 48.2(6) . . . . ?
C15 N1 C11 C12 2.1(7) . . . . ?
Zn1 N1 C11 C12 -173.1(4) . . . . ?
N1 C11 C12 C13 -0.9(8) . . . . ?
C11 C12 C13 C14 -1.1(7) . . . . ?
C11 C12 C13 C16 177.9(5) . . . . ?
C12 C13 C14 C15 1.6(7) . . . . ?
C16 C13 C14 C15 -177.5(5) . . . . ?
C11 N1 C15 C14 -1.6(7) . . . . ?
Zn1 N1 C15 C14 173.7(4) . . . . ?
C13 C14 C15 N1 -0.3(8) . . . . ?
C12 C13 C16 C16 -10.8(10) . . . 3_665 ?
C14 C13 C16 C16 168.1(6) . . . 3_665 ?
C21 N2 C17 C18 -0.5(7) . . . . ?
Zn1 N2 C17 C18 176.6(4) . . . . ?
N2 C17 C18 C19 0.0(8) . . . . ?
C17 C18 C19 C20 0.7(7) . . . . ?
C17 C18 C19 C22 -178.6(5) . . . . ?
C18 C19 C20 C21 -1.0(7) . . . . ?
C22 C19 C20 C21 178.4(5) . . . . ?
C17 N2 C21 C20 0.2(7) . . . . ?
Zn1 N2 C21 C20 -176.9(4) . . . . ?
C19 C20 C21 N2 0.5(8) . . . . ?
C20 C19 C22 C22 -176.2(6) . . . 3_766 ?
C18 C19 C22 C22 3.1(10) . . . 3_766 ?

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
O7 H7D O1 0.82 2.00 2.823(6) 179.4 .
O7 H7C O5 0.82 2.04 2.859(5) 178.9 1_455
O6 H6D O7 0.82 2.05 2.872(6) 179.6 .
O6 H6C O3 0.82 2.13 2.948(6) 179.4 .
O5 H5D O3 0.82 2.07 2.894(5) 179.3 1_655
O5 H5C O6 0.82 2.05 2.867(6) 178.9 .

_diffrn_measured_fraction_theta_max 0.998
_diffrn_reflns_theta_full        25.09
_diffrn_measured_fraction_theta_full 0.998
_refine_diff_density_max         0.711
_refine_diff_density_min         -0.509
_refine_diff_density_rms         0.073

# Attachment '2.cif'

data_2
_database_code_depnum_ccdc_archive 'CCDC 729343'

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C20 H20 N2 O6 Zn'
_chemical_formula_sum            'C20 H20 N2 O6 Zn'
_chemical_formula_weight         449.75

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'
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'
H H 0.0000 0.0000 '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                   8.3194(11)
_cell_length_b                   11.3886(15)
_cell_length_c                   11.444(3)
_cell_angle_alpha                109.818(3)
_cell_angle_beta                 92.908(3)
_cell_angle_gamma                111.323(2)
_cell_volume                     931.3(3)
_cell_formula_units_Z            2
_cell_measurement_temperature    273(2)
_cell_measurement_reflns_used    1166
_cell_measurement_theta_min      2.228
_cell_measurement_theta_max      21.889

_exptl_crystal_description       block
_exptl_crystal_colour            colorless
_exptl_crystal_size_max          0.31
_exptl_crystal_size_mid          0.16
_exptl_crystal_size_min          0.14
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.604
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             464
_exptl_absorpt_coefficient_mu    1.361
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.6777
_exptl_absorpt_correction_T_max  0.8323
_exptl_absorpt_process_details   sadabs

_exptl_special_details           
;
?
;

_diffrn_ambient_temperature      273(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  ?
_diffrn_measurement_method       ?
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            4703
_diffrn_reflns_av_R_equivalents  0.0238
_diffrn_reflns_av_sigmaI/netI    0.0550
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_theta_min         1.93
_diffrn_reflns_theta_max         25.10
_reflns_number_total             3256
_reflns_number_gt                2408
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_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)+(0.0850P)²+0.0000P] 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         3256
_refine_ls_number_parameters     268
_refine_ls_number_restraints     12
_refine_ls_R_factor_all          0.0628
_refine_ls_R_factor_gt           0.0451
_refine_ls_wR_factor_ref         0.1443
_refine_ls_wR_factor_gt          0.1274
_refine_ls_goodness_of_fit_ref   1.094
_refine_ls_restrained_S_all      1.093
_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 0.41517(6) 0.32139(5) 0.24840(5) 0.0327(2) Uani 1 1 d . . .
O1 O 0.2239(4) 0.3668(3) 0.1587(3) 0.0386(7) Uani 1 1 d . . .
O2 O 0.2891(4) 0.4591(3) 0.3664(3) 0.0411(8) Uani 1 1 d . . .
O3 O 0.5029(4) 0.7817(3) -0.0986(3) 0.0430(8) Uani 1 1 d . . .
O4 O 0.2606(5) 0.7511(5) -0.2191(3) 0.0678(11) Uani 1 1 d . . .
O5 O 0.5817(4) 0.3364(3) 0.4020(3) 0.0371(7) Uani 1 1 d D . .
O6 O 0.0778(14) 0.7523(10) 0.5830(9) 0.257(5) Uani 1 1 d DU . .
H6C H 0.0849 0.7679 0.6591 0.308 Uiso 1 1 d RD . .
H6D H -0.0158 0.6948 0.5411 0.308 Uiso 1 1 d RD . .
N1 N 0.6134(5) 0.5125(4) 0.2508(3) 0.0338(8) Uani 1 1 d . . .
N2 N 1.2182(5) 1.1402(3) 0.2543(3) 0.0313(8) Uani 1 1 d . . .
C1 C 0.2155(5) 0.4487(4) 0.2619(4) 0.0322(10) Uani 1 1 d . . .
C2 C 0.1255(6) 0.5449(5) 0.2617(5) 0.0411(11) Uani 1 1 d . . .
H2A H 0.0209 0.4966 0.1952 0.049 Uiso 1 1 calc R . .
H2B H 0.0900 0.5751 0.3422 0.049 Uiso 1 1 calc R . .
C3 C 0.2508(6) 0.6674(5) 0.2403(4) 0.0382(11) Uani 1 1 d . . .
C4 C 0.3993(7) 0.7623(5) 0.3317(5) 0.0462(12) Uani 1 1 d . . .
H4 H 0.4229 0.7499 0.4060 0.055 Uiso 1 1 calc R . .
C5 C 0.5133(6) 0.8760(5) 0.3132(5) 0.0497(13) Uani 1 1 d . . .
H5A H 0.6145 0.9378 0.3739 0.060 Uiso 1 1 calc R . .
C6 C 0.4770(6) 0.8974(5) 0.2058(5) 0.0463(12) Uani 1 1 d . . .
H6 H 0.5536 0.9741 0.1946 0.056 Uiso 1 1 calc R . .
C7 C 0.3269(6) 0.8056(5) 0.1133(4) 0.0371(11) Uani 1 1 d . . .
C8 C 0.2182(6) 0.6909(4) 0.1321(4) 0.0351(10) Uani 1 1 d . . .
H8 H 0.1196 0.6273 0.0697 0.042 Uiso 1 1 calc R . .
C9 C 0.2774(7) 0.8338(5) 0.0007(5) 0.0450(12) Uani 1 1 d . . .
H9A H 0.3146 0.9317 0.0269 0.054 Uiso 1 1 calc R . .
H9B H 0.1500 0.7925 -0.0242 0.054 Uiso 1 1 calc R . .
C10 C 0.3529(7) 0.7836(5) -0.1152(5) 0.0399(11) Uani 1 1 d . . .
C11 C 0.6375(6) 0.5300(5) 0.1427(4) 0.0378(11) Uani 1 1 d . . .
H11 H 0.5758 0.4565 0.0670 0.045 Uiso 1 1 calc R . .
C12 C 0.7492(6) 0.6513(4) 0.1369(4) 0.0389(11) Uani 1 1 d . . .
H12 H 0.7581 0.6595 0.0591 0.047 Uiso 1 1 calc R . .
C13 C 0.8480(5) 0.7608(4) 0.2484(4) 0.0306(10) Uani 1 1 d . . .
C14 C 0.8267(6) 0.7410(5) 0.3612(4) 0.0389(11) Uani 1 1 d . . .
H14 H 0.8924 0.8106 0.4381 0.047 Uiso 1 1 calc R . .
C15 C 0.7080(6) 0.6180(4) 0.3585(4) 0.0370(11) Uani 1 1 d . . .
H15 H 0.6930 0.6078 0.4350 0.044 Uiso 1 1 calc R . .
C16 C 0.9720(6) 0.8915(4) 0.2496(4) 0.0310(10) Uani 1 1 d . . .
C17 C 0.9380(6) 0.9501(5) 0.1686(4) 0.0394(11) Uani 1 1 d . . .
H17 H 0.8318 0.9069 0.1107 0.047 Uiso 1 1 calc R . .
C18 C 1.0620(6) 1.0727(5) 0.1738(4) 0.0420(12) Uani 1 1 d . . .
H18 H 1.0358 1.1104 0.1188 0.050 Uiso 1 1 calc R . .
C19 C 1.2501(6) 1.0841(4) 0.3324(4) 0.0357(10) Uani 1 1 d . . .
H19 H 1.3581 1.1288 0.3884 0.043 Uiso 1 1 calc R . .
C20 C 1.1330(6) 0.9641(4) 0.3351(4) 0.0347(10) Uani 1 1 d . . .
H20 H 1.1608 0.9312 0.3939 0.042 Uiso 1 1 calc R . .
H5C H 0.628(4) 0.397(3) 0.473(2) 0.042 Uiso 1 1 d D . .
H5D H 0.658(4) 0.318(4) 0.366(3) 0.042 Uiso 1 1 d 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 O3 2.029(3) 2_665 ?
Zn1 O5 2.102(3) . ?
Zn1 N2 2.143(3) 1_445 ?
Zn1 O1 2.156(3) . ?
Zn1 N1 2.192(3) . ?
Zn1 O2 2.299(3) . ?
O1 C1 1.256(5) . ?
O2 C1 1.264(5) . ?
O3 C10 1.261(6) . ?
O3 Zn1 2.029(3) 2_665 ?
O4 C10 1.242(6) . ?
O5 H5C 0.822(10) . ?
O5 H5D 0.825(10) . ?
O6 H6C 0.8226 . ?
O6 H6D 0.8018 . ?
N1 C11 1.332(5) . ?
N1 C15 1.339(5) . ?
N2 C19 1.328(5) . ?
N2 C18 1.342(6) . ?
N2 Zn1 2.143(3) 1_665 ?
C1 C2 1.536(6) . ?
C2 C3 1.514(6) . ?
C2 H2A 0.9700 . ?
C2 H2B 0.9700 . ?
C3 C4 1.385(7) . ?
C3 C8 1.387(6) . ?
C4 C5 1.391(7) . ?
C4 H4 0.9300 . ?
C5 C6 1.370(7) . ?
C5 H5A 0.9300 . ?
C6 C7 1.392(7) . ?
C6 H6 0.9300 . ?
C7 C8 1.386(6) . ?
C7 C9 1.502(6) . ?
C8 H8 0.9300 . ?
C9 C10 1.521(7) . ?
C9 H9A 0.9700 . ?
C9 H9B 0.9700 . ?
C11 C12 1.383(6) . ?
C11 H11 0.9300 . ?
C12 C13 1.389(6) . ?
C12 H12 0.9300 . ?
C13 C14 1.393(6) . ?
C13 C16 1.465(6) . ?
C14 C15 1.379(6) . ?
C14 H14 0.9300 . ?
C15 H15 0.9300 . ?
C16 C17 1.384(6) . ?
C16 C20 1.396(6) . ?
C17 C18 1.382(6) . ?
C17 H17 0.9300 . ?
C18 H18 0.9300 . ?
C19 C20 1.372(6) . ?
C19 H19 0.9300 . ?
C20 H20 0.9300 . ?

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 Zn1 O5 101.67(13) 2_665 . ?
O3 Zn1 N2 94.16(13) 2_665 1_445 ?
O5 Zn1 N2 89.96(12) . 1_445 ?
O3 Zn1 O1 102.56(13) 2_665 . ?
O5 Zn1 O1 155.35(13) . . ?
N2 Zn1 O1 92.79(12) 1_445 . ?
O3 Zn1 N1 88.65(13) 2_665 . ?
O5 Zn1 N1 89.27(13) . . ?
N2 Zn1 N1 177.18(13) 1_445 . ?
O1 Zn1 N1 86.79(12) . . ?
O3 Zn1 O2 160.46(12) 2_665 . ?
O5 Zn1 O2 96.52(12) . . ?
N2 Zn1 O2 92.95(12) 1_445 . ?
O1 Zn1 O2 58.89(11) . . ?
N1 Zn1 O2 84.45(13) . . ?
C1 O1 Zn1 93.0(2) . . ?
C1 O2 Zn1 86.3(3) . . ?
C10 O3 Zn1 119.3(3) . 2_665 ?
Zn1 O5 H5C 132(3) . . ?
Zn1 O5 H5D 100(3) . . ?
H5C O5 H5D 109.5(18) . . ?
H6C O6 H6D 113.0 . . ?
C11 N1 C15 117.2(4) . . ?
C11 N1 Zn1 120.1(3) . . ?
C15 N1 Zn1 122.5(3) . . ?
C19 N2 C18 116.7(4) . . ?
C19 N2 Zn1 121.2(3) . 1_665 ?
C18 N2 Zn1 122.0(3) . 1_665 ?
O1 C1 O2 121.0(4) . . ?
O1 C1 C2 119.8(4) . . ?
O2 C1 C2 119.0(4) . . ?
C3 C2 C1 110.0(4) . . ?
C3 C2 H2A 109.7 . . ?
C1 C2 H2A 109.7 . . ?
C3 C2 H2B 109.7 . . ?
C1 C2 H2B 109.7 . . ?
H2A C2 H2B 108.2 . . ?
C4 C3 C8 118.1(4) . . ?
C4 C3 C2 120.3(4) . . ?
C8 C3 C2 121.6(4) . . ?
C3 C4 C5 120.4(4) . . ?
C3 C4 H4 119.8 . . ?
C5 C4 H4 119.8 . . ?
C6 C5 C4 120.2(5) . . ?
C6 C5 H5A 119.9 . . ?
C4 C5 H5A 119.9 . . ?
C5 C6 C7 120.8(4) . . ?
C5 C6 H6 119.6 . . ?
C7 C6 H6 119.6 . . ?
C8 C7 C6 117.9(4) . . ?
C8 C7 C9 120.7(4) . . ?
C6 C7 C9 121.3(4) . . ?
C7 C8 C3 122.5(4) . . ?
C7 C8 H8 118.8 . . ?
C3 C8 H8 118.8 . . ?
C7 C9 C10 116.4(4) . . ?
C7 C9 H9A 108.2 . . ?
C10 C9 H9A 108.2 . . ?
C7 C9 H9B 108.2 . . ?
C10 C9 H9B 108.2 . . ?
H9A C9 H9B 107.3 . . ?
O4 C10 O3 125.8(5) . . ?
O4 C10 C9 115.7(5) . . ?
O3 C10 C9 118.5(4) . . ?
N1 C11 C12 123.6(4) . . ?
N1 C11 H11 118.2 . . ?
C12 C11 H11 118.2 . . ?
C11 C12 C13 119.4(4) . . ?
C11 C12 H12 120.3 . . ?
C13 C12 H12 120.3 . . ?
C12 C13 C14 117.0(4) . . ?
C12 C13 C16 122.5(4) . . ?
C14 C13 C16 120.5(4) . . ?
C15 C14 C13 119.9(4) . . ?
C15 C14 H14 120.1 . . ?
C13 C14 H14 120.1 . . ?
N1 C15 C14 123.0(4) . . ?
N1 C15 H15 118.5 . . ?
C14 C15 H15 118.5 . . ?
C17 C16 C20 116.4(4) . . ?
C17 C16 C13 123.0(4) . . ?
C20 C16 C13 120.6(4) . . ?
C18 C17 C16 120.0(4) . . ?
C18 C17 H17 120.0 . . ?
C16 C17 H17 120.0 . . ?
N2 C18 C17 123.2(4) . . ?
N2 C18 H18 118.4 . . ?
C17 C18 H18 118.4 . . ?
N2 C19 C20 123.8(4) . . ?
N2 C19 H19 118.1 . . ?
C20 C19 H19 118.1 . . ?
C19 C20 C16 120.0(4) . . ?
C19 C20 H20 120.0 . . ?
C16 C20 H20 120.0 . . ?

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
O3 Zn1 O1 C1 -168.3(2) 2_665 . . . ?
O5 Zn1 O1 C1 0.8(4) . . . . ?
N2 Zn1 O1 C1 96.8(2) 1_445 . . . ?
N1 Zn1 O1 C1 -80.4(2) . . . . ?
O2 Zn1 O1 C1 5.0(2) . . . . ?
O3 Zn1 O2 C1 14.8(5) 2_665 . . . ?
O5 Zn1 O2 C1 173.2(2) . . . . ?
N2 Zn1 O2 C1 -96.5(2) 1_445 . . . ?
O1 Zn1 O2 C1 -5.0(2) . . . . ?
N1 Zn1 O2 C1 84.6(2) . . . . ?
O3 Zn1 N1 C11 42.9(3) 2_665 . . . ?
O5 Zn1 N1 C11 144.6(4) . . . . ?
N2 Zn1 N1 C11 -141(3) 1_445 . . . ?
O1 Zn1 N1 C11 -59.8(3) . . . . ?
O2 Zn1 N1 C11 -118.8(3) . . . . ?
O3 Zn1 N1 C15 -140.6(4) 2_665 . . . ?
O5 Zn1 N1 C15 -38.9(4) . . . . ?
N2 Zn1 N1 C15 35(3) 1_445 . . . ?
O1 Zn1 N1 C15 116.8(4) . . . . ?
O2 Zn1 N1 C15 57.7(4) . . . . ?
Zn1 O1 C1 O2 -9.2(4) . . . . ?
Zn1 O1 C1 C2 166.7(3) . . . . ?
Zn1 O2 C1 O1 8.6(4) . . . . ?
Zn1 O2 C1 C2 -167.3(3) . . . . ?
O1 C1 C2 C3 -80.8(5) . . . . ?
O2 C1 C2 C3 95.1(5) . . . . ?
C1 C2 C3 C4 -67.7(6) . . . . ?
C1 C2 C3 C8 114.7(5) . . . . ?
C8 C3 C4 C5 -1.3(7) . . . . ?
C2 C3 C4 C5 -179.0(4) . . . . ?
C3 C4 C5 C6 1.9(8) . . . . ?
C4 C5 C6 C7 -0.5(8) . . . . ?
C5 C6 C7 C8 -1.5(7) . . . . ?
C5 C6 C7 C9 174.7(5) . . . . ?
C6 C7 C8 C3 2.1(7) . . . . ?
C9 C7 C8 C3 -174.1(4) . . . . ?
C4 C3 C8 C7 -0.7(7) . . . . ?
C2 C3 C8 C7 177.0(4) . . . . ?
C8 C7 C9 C10 -94.6(5) . . . . ?
C6 C7 C9 C10 89.4(6) . . . . ?
Zn1 O3 C10 O4 -15.2(6) 2_665 . . . ?
Zn1 O3 C10 C9 166.9(3) 2_665 . . . ?
C7 C9 C10 O4 149.5(5) . . . . ?
C7 C9 C10 O3 -32.4(6) . . . . ?
C15 N1 C11 C12 -2.3(7) . . . . ?
Zn1 N1 C11 C12 174.5(4) . . . . ?
N1 C11 C12 C13 2.5(7) . . . . ?
C11 C12 C13 C14 -0.4(7) . . . . ?
C11 C12 C13 C16 178.6(4) . . . . ?
C12 C13 C14 C15 -1.7(7) . . . . ?
C16 C13 C14 C15 179.3(4) . . . . ?
C11 N1 C15 C14 0.0(7) . . . . ?
Zn1 N1 C15 C14 -176.7(3) . . . . ?
C13 C14 C15 N1 2.0(7) . . . . ?
C12 C13 C16 C17 39.1(7) . . . . ?
C14 C13 C16 C17 -142.0(5) . . . . ?
C12 C13 C16 C20 -141.2(5) . . . . ?
C14 C13 C16 C20 37.7(6) . . . . ?
C20 C16 C17 C18 1.2(7) . . . . ?
C13 C16 C17 C18 -179.1(4) . . . . ?
C19 N2 C18 C17 -0.7(7) . . . . ?
Zn1 N2 C18 C17 174.7(4) 1_665 . . . ?
C16 C17 C18 N2 0.4(8) . . . . ?
C18 N2 C19 C20 -0.6(7) . . . . ?
Zn1 N2 C19 C20 -176.1(3) 1_665 . . . ?
N2 C19 C20 C16 2.2(7) . . . . ?
C17 C16 C20 C19 -2.4(7) . . . . ?
C13 C16 C20 C19 177.9(4) . . . . ?

_diffrn_measured_fraction_theta_max 0.979
_diffrn_reflns_theta_full        25.10
_diffrn_measured_fraction_theta_full 0.979
_refine_diff_density_max         0.573
_refine_diff_density_min         -0.713
_refine_diff_density_rms         0.099

# Attachment '5.cif'

data_5
_database_code_depnum_ccdc_archive 'CCDC 729344'

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C22 H24 N2 O6 Zn'
_chemical_formula_sum            'C22 H24 N2 O6 Zn'
_chemical_formula_weight         477.80

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'
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'
H H 0.0000 0.0000 '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                   6.8963(8)
_cell_length_b                   9.4798(12)
_cell_length_c                   16.697(2)
_cell_angle_alpha                90.660(2)
_cell_angle_beta                 101.526(2)
_cell_angle_gamma                91.251(2)
_cell_volume                     1069.2(2)
_cell_formula_units_Z            2
_cell_measurement_temperature    273(2)
_cell_measurement_reflns_used    1362
_cell_measurement_theta_min      2.490
_cell_measurement_theta_max      22.308

_exptl_crystal_description       block
_exptl_crystal_colour            colorless
_exptl_crystal_size_max          0.15
_exptl_crystal_size_mid          0.11
_exptl_crystal_size_min          0.08
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.484
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             496
_exptl_absorpt_coefficient_mu    1.190
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.8417
_exptl_absorpt_correction_T_max  0.9108
_exptl_absorpt_process_details   sadabs

_exptl_special_details           
;
?
;

_diffrn_ambient_temperature      273(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  ?
_diffrn_measurement_method       ?
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            5374
_diffrn_reflns_av_R_equivalents  0.0251
_diffrn_reflns_av_sigmaI/netI    0.0601
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_theta_min         2.15
_diffrn_reflns_theta_max         25.10
_reflns_number_total             3727
_reflns_number_gt                2748
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_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)+(0.1271P)²+0.0000P] 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         3727
_refine_ls_number_parameters     280
_refine_ls_number_restraints     12
_refine_ls_R_factor_all          0.0786
_refine_ls_R_factor_gt           0.0625
_refine_ls_wR_factor_ref         0.1919
_refine_ls_wR_factor_gt          0.1825
_refine_ls_goodness_of_fit_ref   1.055
_refine_ls_restrained_S_all      1.054
_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 0.87533(8) 0.76502(6) 0.19431(3) 0.0377(3) Uani 1 1 d . . .
O1 O 1.1544(8) 0.8636(5) 0.3356(3) 0.0840(15) Uani 1 1 d . . .
O2 O 0.9673(6) 0.9590(4) 0.2298(2) 0.0525(10) Uani 1 1 d . . .
O3 O 0.8403(6) 1.5095(5) 0.1111(3) 0.0646(12) Uani 1 1 d . . .
O4 O 1.0853(5) 1.6605(4) 0.1615(2) 0.0530(10) Uani 1 1 d . . .
N1 N 0.6260(6) 0.8253(4) 0.1121(2) 0.0355(9) Uani 1 1 d . . .
N2 N 0.7523(6) 0.6624(5) 0.2798(3) 0.0432(10) Uani 1 1 d . . .
O5 O 0.442(3) 0.0839(19) 0.5506(12) 0.382(10) Uani 1 1 d U . .
H5C H 0.4793 0.0279 0.5193 0.458 Uiso 1 1 d R . .
H5D H 0.5508 0.0984 0.5804 0.458 Uiso 1 1 d R . .
O6 O 0.019(2) 0.1679(17) 0.5181(11) 0.341(8) Uani 1 1 d U . .
H6D H 0.1362 0.1465 0.5270 0.409 Uiso 1 1 d R . .
H6C H -0.0242 0.1616 0.5602 0.409 Uiso 1 1 d R . .
C1 C 1.0844(8) 0.9684(6) 0.2974(3) 0.0462(13) Uani 1 1 d . . .
C2 C 1.1403(9) 1.1147(6) 0.3312(3) 0.0506(14) Uani 1 1 d . . .
H2A H 1.2171 1.1082 0.3863 0.061 Uiso 1 1 calc R . .
H2B H 1.0208 1.1650 0.3340 0.061 Uiso 1 1 calc R . .
C3 C 1.2603(8) 1.1983(5) 0.2793(3) 0.0429(12) Uani 1 1 d . . .
C4 C 1.4643(9) 1.1897(6) 0.2914(4) 0.0569(16) Uani 1 1 d . . .
H4 H 1.5300 1.1321 0.3322 0.068 Uiso 1 1 calc R . .
C5 C 1.5702(8) 1.2630(7) 0.2452(4) 0.0617(17) Uani 1 1 d . . .
H5 H 1.7072 1.2558 0.2551 0.074 Uiso 1 1 calc R . .
C6 C 1.4779(9) 1.3478(6) 0.1839(4) 0.0563(16) Uani 1 1 d . . .
H6 H 1.5519 1.3980 0.1525 0.068 Uiso 1 1 calc R . .
C7 C 1.2709(8) 1.3585(5) 0.1688(3) 0.0427(13) Uani 1 1 d . . .
C8 C 1.1665(7) 1.2837(5) 0.2168(3) 0.0390(12) Uani 1 1 d . . .
H8 H 1.0295 1.2903 0.2072 0.047 Uiso 1 1 calc R . .
C9 C 1.1704(9) 1.4501(6) 0.1004(4) 0.0513(14) Uani 1 1 d . . .
H9A H 1.2699 1.5075 0.0816 0.062 Uiso 1 1 calc R . .
H9B H 1.1052 1.3902 0.0551 0.062 Uiso 1 1 calc R . .
C10 C 1.0197(8) 1.5454(6) 0.1256(3) 0.0443(13) Uani 1 1 d . . .
C11 C 0.5419(7) 0.9431(6) 0.1311(3) 0.0465(13) Uani 1 1 d . . .
H11 H 0.6122 1.0012 0.1727 0.056 Uiso 1 1 calc R . .
C12 C 0.3584(8) 0.9828(5) 0.0928(3) 0.0437(13) Uani 1 1 d . . .
H12 H 0.3059 1.0655 0.1090 0.052 Uiso 1 1 calc R . .
C13 C 0.2505(7) 0.9011(5) 0.0303(3) 0.0359(11) Uani 1 1 d . . .
C14 C 0.3408(7) 0.7810(6) 0.0085(3) 0.0422(12) Uani 1 1 d . . .
H14 H 0.2761 0.7237 -0.0347 0.051 Uiso 1 1 calc R . .
C15 C 0.5262(7) 0.7466(5) 0.0505(3) 0.0399(12) Uani 1 1 d . . .
H15 H 0.5836 0.6653 0.0353 0.048 Uiso 1 1 calc R . .
C16 C 0.0432(8) 0.9336(6) -0.0136(3) 0.0452(13) Uani 1 1 d . . .
H16A H 0.0431 0.9402 -0.0715 0.054 Uiso 1 1 calc R . .
H16B H -0.0434 0.8546 -0.0067 0.054 Uiso 1 1 calc R . .
C17 C 0.5638(9) 0.6780(7) 0.2852(4) 0.0610(16) Uani 1 1 d . . .
H17 H 0.4853 0.7366 0.2486 0.073 Uiso 1 1 calc R . .
C18 C 0.4808(10) 0.6097(8) 0.3437(4) 0.072(2) Uani 1 1 d . . .
H18 H 0.3484 0.6232 0.3452 0.086 Uiso 1 1 calc R . .
C19 C 0.5904(10) 0.5223(7) 0.3995(4) 0.0588(16) Uani 1 1 d . . .
C20 C 0.7858(10) 0.5069(7) 0.3923(4) 0.0633(17) Uani 1 1 d . . .
H20 H 0.8678 0.4491 0.4282 0.076 Uiso 1 1 calc R . .
C21 C 0.8591(9) 0.5763(7) 0.3324(4) 0.0559(15) Uani 1 1 d . . .
H21 H 0.9900 0.5623 0.3286 0.067 Uiso 1 1 calc R . .
C22 C 0.5023(14) 0.4533(8) 0.4641(5) 0.085(2) Uani 1 1 d . . .
H22A H 0.5777 0.3706 0.4826 0.102 Uiso 1 1 calc R . .
H22B H 0.3682 0.4218 0.4403 0.102 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
Zn1 O4 1.935(4) 1_545 ?
Zn1 O2 1.977(4) . ?
Zn1 N2 2.046(4) . ?
Zn1 N1 2.070(4) . ?
O1 C1 1.240(6) . ?
O2 C1 1.251(7) . ?
O3 C10 1.251(6) . ?
O4 C10 1.268(7) . ?
O4 Zn1 1.935(4) 1_565 ?
N1 C15 1.328(6) . ?
N1 C11 1.333(6) . ?
N2 C21 1.329(7) . ?
N2 C17 1.332(7) . ?
O5 H5C 0.8200 . ?
O5 H5D 0.8200 . ?
O6 H6D 0.8200 . ?
O6 H6C 0.8201 . ?
C1 C2 1.504(8) . ?
C2 C3 1.528(7) . ?
C2 H2A 0.9700 . ?
C2 H2B 0.9700 . ?
C3 C4 1.385(8) . ?
C3 C8 1.392(7) . ?
C4 C5 1.351(9) . ?
C4 H4 0.9300 . ?
C5 C6 1.371(9) . ?
C5 H5 0.9300 . ?
C6 C7 1.405(8) . ?
C6 H6 0.9300 . ?
C7 C8 1.373(7) . ?
C7 C9 1.506(7) . ?
C8 H8 0.9300 . ?
C9 C10 1.510(7) . ?
C9 H9A 0.9700 . ?
C9 H9B 0.9700 . ?
C11 C12 1.362(7) . ?
C11 H11 0.9300 . ?
C12 C13 1.375(7) . ?
C12 H12 0.9300 . ?
C13 C14 1.389(7) . ?
C13 C16 1.510(7) . ?
C14 C15 1.378(7) . ?
C14 H14 0.9300 . ?
C15 H15 0.9300 . ?
C16 C16 1.508(10) 2_575 ?
C16 H16A 0.9700 . ?
C16 H16B 0.9700 . ?
C17 C18 1.386(8) . ?
C17 H17 0.9300 . ?
C18 C19 1.375(9) . ?
C18 H18 0.9300 . ?
C19 C20 1.387(9) . ?
C19 C22 1.489(8) . ?
C20 C21 1.375(8) . ?
C20 H20 0.9300 . ?
C21 H21 0.9300 . ?
C22 C22 1.489(14) 2_666 ?
C22 H22A 0.9700 . ?
C22 H22B 0.9700 . ?

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
O4 Zn1 O2 110.76(16) 1_545 . ?
O4 Zn1 N2 112.72(17) 1_545 . ?
O2 Zn1 N2 112.35(18) . . ?
O4 Zn1 N1 122.68(17) 1_545 . ?
O2 Zn1 N1 95.45(16) . . ?
N2 Zn1 N1 101.57(16) . . ?
C1 O2 Zn1 115.0(3) . . ?
C10 O4 Zn1 111.2(3) . 1_565 ?
C15 N1 C11 117.3(4) . . ?
C15 N1 Zn1 125.6(3) . . ?
C11 N1 Zn1 116.1(3) . . ?
C21 N2 C17 117.3(5) . . ?
C21 N2 Zn1 120.6(4) . . ?
C17 N2 Zn1 122.1(4) . . ?
H5C O5 H5D 96.5 . . ?
H6D O6 H6C 109.8 . . ?
O1 C1 O2 122.7(5) . . ?
O1 C1 C2 120.4(5) . . ?
O2 C1 C2 116.8(5) . . ?
C1 C2 C3 112.5(5) . . ?
C1 C2 H2A 109.1 . . ?
C3 C2 H2A 109.1 . . ?
C1 C2 H2B 109.1 . . ?
C3 C2 H2B 109.1 . . ?
H2A C2 H2B 107.8 . . ?
C4 C3 C8 117.7(5) . . ?
C4 C3 C2 121.7(5) . . ?
C8 C3 C2 120.7(5) . . ?
C5 C4 C3 121.6(6) . . ?
C5 C4 H4 119.2 . . ?
C3 C4 H4 119.2 . . ?
C4 C5 C6 120.7(6) . . ?
C4 C5 H5 119.6 . . ?
C6 C5 H5 119.6 . . ?
C5 C6 C7 119.7(6) . . ?
C5 C6 H6 120.1 . . ?
C7 C6 H6 120.1 . . ?
C8 C7 C6 118.5(5) . . ?
C8 C7 C9 122.1(5) . . ?
C6 C7 C9 119.4(5) . . ?
C7 C8 C3 121.8(5) . . ?
C7 C8 H8 119.1 . . ?
C3 C8 H8 119.1 . . ?
C10 C9 C7 113.0(4) . . ?
C10 C9 H9A 109.0 . . ?
C7 C9 H9A 109.0 . . ?
C10 C9 H9B 109.0 . . ?
C7 C9 H9B 109.0 . . ?
H9A C9 H9B 107.8 . . ?
O3 C10 O4 123.2(5) . . ?
O3 C10 C9 120.2(5) . . ?
O4 C10 C9 116.6(5) . . ?
N1 C11 C12 123.4(5) . . ?
N1 C11 H11 118.3 . . ?
C12 C11 H11 118.3 . . ?
C11 C12 C13 120.2(5) . . ?
C11 C12 H12 119.9 . . ?
C13 C12 H12 119.9 . . ?
C12 C13 C14 116.4(5) . . ?
C12 C13 C16 124.0(5) . . ?
C14 C13 C16 119.6(5) . . ?
C15 C14 C13 120.1(5) . . ?
C15 C14 H14 119.9 . . ?
C13 C14 H14 119.9 . . ?
N1 C15 C14 122.4(5) . . ?
N1 C15 H15 118.8 . . ?
C14 C15 H15 118.8 . . ?
C16 C16 C13 116.1(6) 2_575 . ?
C16 C16 H16A 108.3 2_575 . ?
C13 C16 H16A 108.3 . . ?
C16 C16 H16B 108.3 2_575 . ?
C13 C16 H16B 108.3 . . ?
H16A C16 H16B 107.4 . . ?
N2 C17 C18 122.1(6) . . ?
N2 C17 H17 118.9 . . ?
C18 C17 H17 118.9 . . ?
C19 C18 C17 121.3(6) . . ?
C19 C18 H18 119.4 . . ?
C17 C18 H18 119.4 . . ?
C18 C19 C20 115.5(6) . . ?
C18 C19 C22 121.0(7) . . ?
C20 C19 C22 123.5(7) . . ?
C21 C20 C19 120.5(6) . . ?
C21 C20 H20 119.7 . . ?
C19 C20 H20 119.7 . . ?
N2 C21 C20 123.3(6) . . ?
N2 C21 H21 118.4 . . ?
C20 C21 H21 118.4 . . ?
C19 C22 C22 113.8(8) . 2_666 ?
C19 C22 H22A 108.8 . . ?
C22 C22 H22A 108.8 2_666 . ?
C19 C22 H22B 108.8 . . ?
C22 C22 H22B 108.8 2_666 . ?
H22A C22 H22B 107.7 . . ?

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
O4 Zn1 O2 C1 -72.5(4) 1_545 . . . ?
N2 Zn1 O2 C1 54.6(4) . . . . ?
N1 Zn1 O2 C1 159.5(4) . . . . ?
O4 Zn1 N1 C15 41.0(5) 1_545 . . . ?
O2 Zn1 N1 C15 159.9(4) . . . . ?
N2 Zn1 N1 C15 -85.9(4) . . . . ?
O4 Zn1 N1 C11 -150.6(4) 1_545 . . . ?
O2 Zn1 N1 C11 -31.7(4) . . . . ?
N2 Zn1 N1 C11 82.5(4) . . . . ?
O4 Zn1 N2 C21 29.6(5) 1_545 . . . ?
O2 Zn1 N2 C21 -96.4(5) . . . . ?
N1 Zn1 N2 C21 162.7(4) . . . . ?
O4 Zn1 N2 C17 -150.2(5) 1_545 . . . ?
O2 Zn1 N2 C17 83.8(5) . . . . ?
N1 Zn1 N2 C17 -17.1(5) . . . . ?
Zn1 O2 C1 O1 7.2(8) . . . . ?
Zn1 O2 C1 C2 -173.3(4) . . . . ?
O1 C1 C2 C3 113.4(6) . . . . ?
O2 C1 C2 C3 -66.1(7) . . . . ?
C1 C2 C3 C4 -86.7(6) . . . . ?
C1 C2 C3 C8 91.9(6) . . . . ?
C8 C3 C4 C5 1.0(8) . . . . ?
C2 C3 C4 C5 179.6(5) . . . . ?
C3 C4 C5 C6 -0.7(9) . . . . ?
C4 C5 C6 C7 -0.1(9) . . . . ?
C5 C6 C7 C8 0.5(8) . . . . ?
C5 C6 C7 C9 -179.0(5) . . . . ?
C6 C7 C8 C3 -0.1(7) . . . . ?
C9 C7 C8 C3 179.4(5) . . . . ?
C4 C3 C8 C7 -0.6(8) . . . . ?
C2 C3 C8 C7 -179.2(4) . . . . ?
C8 C7 C9 C10 47.4(7) . . . . ?
C6 C7 C9 C10 -133.1(5) . . . . ?
Zn1 O4 C10 O3 2.7(7) 1_565 . . . ?
Zn1 O4 C10 C9 -177.1(3) 1_565 . . . ?
C7 C9 C10 O3 -96.5(6) . . . . ?
C7 C9 C10 O4 83.3(6) . . . . ?
C15 N1 C11 C12 2.4(8) . . . . ?
Zn1 N1 C11 C12 -167.0(4) . . . . ?
N1 C11 C12 C13 -0.9(9) . . . . ?
C11 C12 C13 C14 -1.4(8) . . . . ?
C11 C12 C13 C16 177.6(5) . . . . ?
C12 C13 C14 C15 2.1(7) . . . . ?
C16 C13 C14 C15 -176.9(5) . . . . ?
C11 N1 C15 C14 -1.7(7) . . . . ?
Zn1 N1 C15 C14 166.6(4) . . . . ?
C13 C14 C15 N1 -0.6(8) . . . . ?
C12 C13 C16 C16 1.4(9) . . . 2_575 ?
C14 C13 C16 C16 -179.6(6) . . . 2_575 ?
C21 N2 C17 C18 0.9(10) . . . . ?
Zn1 N2 C17 C18 -179.3(5) . . . . ?
N2 C17 C18 C19 0.2(11) . . . . ?
C17 C18 C19 C20 -0.7(10) . . . . ?
C17 C18 C19 C22 177.8(6) . . . . ?
C18 C19 C20 C21 0.0(10) . . . . ?
C22 C19 C20 C21 -178.4(6) . . . . ?
C17 N2 C21 C20 -1.7(9) . . . . ?
Zn1 N2 C21 C20 178.6(5) . . . . ?
C19 C20 C21 N2 1.2(10) . . . . ?
C18 C19 C22 C22 -81.0(12) . . . 2_666 ?
C20 C19 C22 C22 97.4(12) . . . 2_666 ?

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
O6 H6C O1 0.82 2.12 2.943(18) 175.9 2_666
O6 H6D O5 0.82 2.17 2.99(2) 178.4 .
O5 H5D O1 0.82 2.25 3.07(2) 178.6 2_766
O5 H5C O5 0.82 1.74 2.56(4) 177.1 2_656

_diffrn_measured_fraction_theta_max 0.981
_diffrn_reflns_theta_full        25.10
_diffrn_measured_fraction_theta_full 0.981
_refine_diff_density_max         1.265
_refine_diff_density_min         -0.622
_refine_diff_density_rms         0.115

# Attachment '3.cif'

data_3
_database_code_depnum_ccdc_archive 'CCDC 729345'

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C21 H20 N2 O5 Zn'
_chemical_formula_sum            'C21 H20 N2 O5 Zn'
_chemical_formula_weight         445.76

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'
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'
H H 0.0000 0.0000 '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                   9.562(4)
_cell_length_b                   10.592(2)
_cell_length_c                   10.940(2)
_cell_angle_alpha                115.892(4)
_cell_angle_beta                 105.631(5)
_cell_angle_gamma                95.654(5)
_cell_volume                     929.6(5)
_cell_formula_units_Z            2
_cell_measurement_temperature    273(2)
_cell_measurement_reflns_used    521
_cell_measurement_theta_min      2.208
_cell_measurement_theta_max      18.826

_exptl_crystal_description       block
_exptl_crystal_colour            colorless
_exptl_crystal_size_max          0.40
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.15
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.593
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             460
_exptl_absorpt_coefficient_mu    1.359
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.6125
_exptl_absorpt_correction_T_max  0.8221
_exptl_absorpt_process_details   sadabs

_exptl_special_details           
;
?
;

_diffrn_ambient_temperature      273(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  ?
_diffrn_measurement_method       ?
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        0
_diffrn_reflns_number            4608
_diffrn_reflns_av_R_equivalents  0.0438
_diffrn_reflns_av_sigmaI/netI    0.1365
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_limit_l_max       9
_diffrn_reflns_theta_min         2.21
_diffrn_reflns_theta_max         25.10
_reflns_number_total             3177
_reflns_number_gt                1785
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'Bruker SMART'
_computing_cell_refinement       'Bruker SMART'
_computing_data_reduction        'Brucker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Brucker 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)+(0.0608P)²+0.2000P] 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       0.013(2)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_number_reflns         3177
_refine_ls_number_parameters     265
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1103
_refine_ls_R_factor_gt           0.0673
_refine_ls_wR_factor_ref         0.1567
_refine_ls_wR_factor_gt          0.1481
_refine_ls_goodness_of_fit_ref   1.064
_refine_ls_restrained_S_all      1.064
_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
O4 O 0.8555(5) 0.9586(5) 0.2490(5) 0.0497(14) Uani 1 1 d . . .
O3 O 0.6921(5) 0.8329(5) 0.2876(5) 0.0485(14) Uani 1 1 d . . .
N2 N 0.6140(6) 0.7596(5) 0.9698(5) 0.0294(13) Uani 1 1 d . . .
C18 C 0.7120(8) 0.7643(7) 0.9038(7) 0.0366(18) Uani 1 1 d . . .
H18 H 0.7778 0.8527 0.9379 0.044 Uiso 1 1 calc R . .
C17 C 0.7200(7) 0.6446(7) 0.7881(7) 0.0356(18) Uani 1 1 d . . .
H17 H 0.7887 0.6531 0.7444 0.043 Uiso 1 1 calc R . .
C19 C 0.5257(7) 0.6305(7) 0.9204(7) 0.0351(18) Uani 1 1 d . . .
H19 H 0.4582 0.6252 0.9663 0.042 Uiso 1 1 calc R . .
C20 C 0.5257(7) 0.5041(7) 0.8068(7) 0.0350(17) Uani 1 1 d . . .
H20 H 0.4612 0.4167 0.7779 0.042 Uiso 1 1 calc R . .
C16 C 0.6244(7) 0.5106(7) 0.7367(6) 0.0306(17) Uani 1 1 d . . .
Zn1 Zn 0.62275(9) -0.04474(8) 0.16027(8) 0.0334(3) Uani 1 1 d . . .
O1 O 0.6725(6) 0.0860(5) 0.0785(5) 0.0562(15) Uani 1 1 d . . .
O2 O 0.5966(5) 0.1055(5) -0.1227(5) 0.0371(12) Uani 1 1 d . . .
N1 N 0.6358(6) 0.1434(6) 0.3579(5) 0.0321(14) Uani 1 1 d . . .
C14 C 0.6151(7) 0.2444(7) 0.5956(7) 0.0394(18) Uani 1 1 d . . .
H14 H 0.6024 0.2285 0.6695 0.047 Uiso 1 1 calc R . .
C15 C 0.6191(7) 0.1302(7) 0.4705(7) 0.0383(18) Uani 1 1 d . . .
H15 H 0.6097 0.0391 0.4642 0.046 Uiso 1 1 calc R . .
C12 C 0.6503(8) 0.3954(7) 0.4932(7) 0.0416(19) Uani 1 1 d . . .
H12 H 0.6636 0.4855 0.4974 0.050 Uiso 1 1 calc R . .
C1 C 0.6958(8) 0.1189(6) -0.0117(8) 0.0342(17) Uani 1 1 d . . .
C8 C 0.8583(8) 0.4384(7) 0.0433(7) 0.0406(19) Uani 1 1 d . . .
H8 H 0.8285 0.3954 -0.0571 0.049 Uiso 1 1 calc R . .
C13 C 0.6300(7) 0.3822(7) 0.6098(7) 0.0327(17) Uani 1 1 d . . .
C9 C 0.9485(8) 0.8167(7) 0.3605(7) 0.0423(19) Uani 1 1 d . . .
H9A H 1.0436 0.8625 0.3643 0.051 Uiso 1 1 calc R . .
H9B H 0.9550 0.8432 0.4591 0.051 Uiso 1 1 calc R . .
C7 C 0.8775(8) 0.5846(7) 0.1224(7) 0.0421(19) Uani 1 1 d . . .
H7 H 0.8616 0.6389 0.0746 0.051 Uiso 1 1 calc R . .
C3 C 0.8819(7) 0.3536(7) 0.1088(7) 0.0329(17) Uani 1 1 d . . .
C2 C 0.8586(7) 0.1929(7) 0.0209(8) 0.0420(19) Uani 1 1 d . . .
H2A H 0.9282 0.1588 0.0746 0.050 Uiso 1 1 calc R . .
H2B H 0.8761 0.1696 -0.0689 0.050 Uiso 1 1 calc R . .
C5 C 0.9442(8) 0.5694(8) 0.3394(7) 0.046(2) Uani 1 1 d . . .
H5 H 0.9736 0.6117 0.4398 0.056 Uiso 1 1 calc R . .
C4 C 0.9247(8) 0.4207(8) 0.2576(8) 0.0440(19) Uani 1 1 d . . .
H4 H 0.9410 0.3655 0.3045 0.053 Uiso 1 1 calc R . .
C6 C 0.9208(7) 0.6550(7) 0.2745(7) 0.0363(18) Uani 1 1 d . . .
C11 C 0.6506(8) 0.2754(7) 0.3727(7) 0.0423(19) Uani 1 1 d . . .
H11 H 0.6619 0.2879 0.2966 0.051 Uiso 1 1 calc R . .
C21 C 0.2370(10) 0.1330(10) 0.3616(10) 0.073(3) Uani 1 1 d . . .
H21A H 0.3170 0.1839 0.3503 0.109 Uiso 1 1 calc R . .
H21B H 0.2380 0.0326 0.3233 0.109 Uiso 1 1 calc R . .
H21C H 0.2501 0.1739 0.4627 0.109 Uiso 1 1 calc R . .
O5 O 0.1031(6) 0.1449(8) 0.2887(9) 0.099(3) Uani 1 1 d . . .
H5A H 0.0349 0.1037 0.3007 0.149 Uiso 1 1 calc R . .
C10 C 0.8261(8) 0.8715(7) 0.2956(7) 0.0373(18) 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
O4 C10 1.275(8) . ?
O4 Zn1 2.165(5) 1_565 ?
O3 C10 1.274(8) . ?
O3 Zn1 2.304(5) 1_565 ?
N2 C19 1.325(8) . ?
N2 C18 1.337(8) . ?
N2 Zn1 2.178(5) 1_566 ?
C18 C17 1.373(9) . ?
C18 H18 0.9300 . ?
C17 C16 1.392(8) . ?
C17 H17 0.9300 . ?
C19 C20 1.373(9) . ?
C19 H19 0.9300 . ?
C20 C16 1.380(9) . ?
C20 H20 0.9300 . ?
C16 C13 1.479(8) . ?
Zn1 O2 2.005(4) 2_655 ?
Zn1 O1 2.031(5) . ?
Zn1 O4 2.165(5) 1_545 ?
Zn1 N1 2.168(5) . ?
Zn1 N2 2.178(5) 1_544 ?
Zn1 O3 2.304(5) 1_545 ?
Zn1 C10 2.588(7) 1_545 ?
O1 C1 1.245(8) . ?
O2 C1 1.264(8) . ?
O2 Zn1 2.005(4) 2_655 ?
N1 C11 1.325(8) . ?
N1 C15 1.347(8) . ?
C14 C13 1.387(9) . ?
C14 C15 1.389(9) . ?
C14 H14 0.9300 . ?
C15 H15 0.9300 . ?
C12 C11 1.375(9) . ?
C12 C13 1.403(9) . ?
C12 H12 0.9300 . ?
C1 C2 1.542(9) . ?
C8 C7 1.367(9) . ?
C8 C3 1.373(9) . ?
C8 H8 0.9300 . ?
C9 C6 1.503(9) . ?
C9 C10 1.502(9) . ?
C9 H9A 0.9700 . ?
C9 H9B 0.9700 . ?
C7 C6 1.407(9) . ?
C7 H7 0.9300 . ?
C3 C4 1.377(9) . ?
C3 C2 1.501(9) . ?
C2 H2A 0.9700 . ?
C2 H2B 0.9700 . ?
C5 C6 1.376(9) . ?
C5 C4 1.392(9) . ?
C5 H5 0.9300 . ?
C4 H4 0.9300 . ?
C11 H11 0.9300 . ?
C21 O5 1.365(9) . ?
C21 H21A 0.9600 . ?
C21 H21B 0.9600 . ?
C21 H21C 0.9600 . ?
O5 H5A 0.8200 . ?
C10 Zn1 2.588(7) 1_565 ?

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
C10 O4 Zn1 94.0(4) . 1_565 ?
C10 O3 Zn1 87.7(4) . 1_565 ?
C19 N2 C18 116.3(6) . . ?
C19 N2 Zn1 124.3(5) . 1_566 ?
C18 N2 Zn1 119.1(4) . 1_566 ?
N2 C18 C17 123.1(6) . . ?
N2 C18 H18 118.5 . . ?
C17 C18 H18 118.5 . . ?
C18 C17 C16 119.5(6) . . ?
C18 C17 H17 120.2 . . ?
C16 C17 H17 120.2 . . ?
N2 C19 C20 125.3(7) . . ?
N2 C19 H19 117.4 . . ?
C20 C19 H19 117.4 . . ?
C19 C20 C16 118.0(6) . . ?
C19 C20 H20 121.0 . . ?
C16 C20 H20 121.0 . . ?
C20 C16 C17 117.8(6) . . ?
C20 C16 C13 122.6(6) . . ?
C17 C16 C13 119.7(6) . . ?
O2 Zn1 O1 114.1(2) 2_655 . ?
O2 Zn1 O4 152.97(19) 2_655 1_545 ?
O1 Zn1 O4 93.0(2) . 1_545 ?
O2 Zn1 N1 87.54(19) 2_655 . ?
O1 Zn1 N1 90.0(2) . . ?
O4 Zn1 N1 92.39(19) 1_545 . ?
O2 Zn1 N2 92.78(19) 2_655 1_544 ?
O1 Zn1 N2 93.1(2) . 1_544 ?
O4 Zn1 N2 85.70(18) 1_545 1_544 ?
N1 Zn1 N2 176.4(2) . 1_544 ?
O2 Zn1 O3 94.17(18) 2_655 1_545 ?
O1 Zn1 O3 151.8(2) . 1_545 ?
O4 Zn1 O3 58.80(18) 1_545 1_545 ?
N1 Zn1 O3 90.26(19) . 1_545 ?
N2 Zn1 O3 86.16(18) 1_544 1_545 ?
O2 Zn1 C10 123.6(2) 2_655 1_545 ?
O1 Zn1 C10 122.4(2) . 1_545 ?
O4 Zn1 C10 29.44(19) 1_545 1_545 ?
N1 Zn1 C10 93.3(2) . 1_545 ?
N2 Zn1 C10 83.50(19) 1_544 1_545 ?
O3 Zn1 C10 29.47(18) 1_545 1_545 ?
C1 O1 Zn1 157.7(4) . . ?
C1 O2 Zn1 121.8(4) . 2_655 ?
C11 N1 C15 115.8(6) . . ?
C11 N1 Zn1 122.9(5) . . ?
C15 N1 Zn1 121.1(4) . . ?
C13 C14 C15 119.8(7) . . ?
C13 C14 H14 120.1 . . ?
C15 C14 H14 120.1 . . ?
N1 C15 C14 124.0(7) . . ?
N1 C15 H15 118.0 . . ?
C14 C15 H15 118.0 . . ?
C11 C12 C13 120.2(7) . . ?
C11 C12 H12 119.9 . . ?
C13 C12 H12 119.9 . . ?
O1 C1 O2 125.6(6) . . ?
O1 C1 C2 117.1(6) . . ?
O2 C1 C2 117.1(6) . . ?
C7 C8 C3 121.5(6) . . ?
C7 C8 H8 119.3 . . ?
C3 C8 H8 119.3 . . ?
C14 C13 C12 115.8(6) . . ?
C14 C13 C16 124.2(6) . . ?
C12 C13 C16 120.0(6) . . ?
C6 C9 C10 111.8(5) . . ?
C6 C9 H9A 109.3 . . ?
C10 C9 H9A 109.3 . . ?
C6 C9 H9B 109.3 . . ?
C10 C9 H9B 109.3 . . ?
H9A C9 H9B 107.9 . . ?
C8 C7 C6 121.6(7) . . ?
C8 C7 H7 119.2 . . ?
C6 C7 H7 119.2 . . ?
C8 C3 C4 117.7(6) . . ?
C8 C3 C2 121.1(6) . . ?
C4 C3 C2 121.1(6) . . ?
C3 C2 C1 108.3(6) . . ?
C3 C2 H2A 110.0 . . ?
C1 C2 H2A 110.0 . . ?
C3 C2 H2B 110.0 . . ?
C1 C2 H2B 110.0 . . ?
H2A C2 H2B 108.4 . . ?
C6 C5 C4 121.2(7) . . ?
C6 C5 H5 119.4 . . ?
C4 C5 H5 119.4 . . ?
C3 C4 C5 121.3(7) . . ?
C3 C4 H4 119.3 . . ?
C5 C4 H4 119.3 . . ?
C5 C6 C7 116.6(6) . . ?
C5 C6 C9 122.3(6) . . ?
C7 C6 C9 121.0(6) . . ?
N1 C11 C12 124.4(7) . . ?
N1 C11 H11 117.8 . . ?
C12 C11 H11 117.8 . . ?
O5 C21 H21A 109.5 . . ?
O5 C21 H21B 109.5 . . ?
H21A C21 H21B 109.5 . . ?
O5 C21 H21C 109.5 . . ?
H21A C21 H21C 109.5 . . ?
H21B C21 H21C 109.5 . . ?
C21 O5 H5A 109.5 . . ?
O3 C10 O4 119.1(7) . . ?
O3 C10 C9 120.5(6) . . ?
O4 C10 C9 120.4(7) . . ?
O3 C10 Zn1 62.8(4) . 1_565 ?
O4 C10 Zn1 56.6(4) . 1_565 ?
C9 C10 Zn1 174.2(5) . 1_565 ?

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
C19 N2 C18 C17 2.0(10) . . . . ?
Zn1 N2 C18 C17 176.4(5) 1_566 . . . ?
N2 C18 C17 C16 -1.1(11) . . . . ?
C18 N2 C19 C20 -1.2(10) . . . . ?
Zn1 N2 C19 C20 -175.2(5) 1_566 . . . ?
N2 C19 C20 C16 -0.5(11) . . . . ?
C19 C20 C16 C17 1.4(10) . . . . ?
C19 C20 C16 C13 -177.7(6) . . . . ?
C18 C17 C16 C20 -0.7(10) . . . . ?
C18 C17 C16 C13 178.4(6) . . . . ?
O2 Zn1 O1 C1 -90.5(14) 2_655 . . . ?
O4 Zn1 O1 C1 89.8(14) 1_545 . . . ?
N1 Zn1 O1 C1 -177.8(14) . . . . ?
N2 Zn1 O1 C1 4.0(14) 1_544 . . . ?
O3 Zn1 O1 C1 91.6(14) 1_545 . . . ?
C10 Zn1 O1 C1 88.2(14) 1_545 . . . ?
O2 Zn1 N1 C11 -106.2(5) 2_655 . . . ?
O1 Zn1 N1 C11 7.8(6) . . . . ?
O4 Zn1 N1 C11 100.8(5) 1_545 . . . ?
N2 Zn1 N1 C11 158(3) 1_544 . . . ?
O3 Zn1 N1 C11 159.6(5) 1_545 . . . ?
C10 Zn1 N1 C11 130.3(5) 1_545 . . . ?
O2 Zn1 N1 C15 69.2(5) 2_655 . . . ?
O1 Zn1 N1 C15 -176.7(5) . . . . ?
O4 Zn1 N1 C15 -83.7(5) 1_545 . . . ?
N2 Zn1 N1 C15 -26(4) 1_544 . . . ?
O3 Zn1 N1 C15 -24.9(5) 1_545 . . . ?
C10 Zn1 N1 C15 -54.2(5) 1_545 . . . ?
C11 N1 C15 C14 0.8(10) . . . . ?
Zn1 N1 C15 C14 -175.0(5) . . . . ?
C13 C14 C15 N1 -0.6(11) . . . . ?
Zn1 O1 C1 O2 75.1(17) . . . . ?
Zn1 O1 C1 C2 -109.7(13) . . . . ?
Zn1 O2 C1 O1 6.2(9) 2_655 . . . ?
Zn1 O2 C1 C2 -169.0(4) 2_655 . . . ?
C15 C14 C13 C12 -0.7(10) . . . . ?
C15 C14 C13 C16 178.8(6) . . . . ?
C11 C12 C13 C14 1.7(10) . . . . ?
C11 C12 C13 C16 -177.8(6) . . . . ?
C20 C16 C13 C14 -39.3(10) . . . . ?
C17 C16 C13 C14 141.6(7) . . . . ?
C20 C16 C13 C12 140.1(7) . . . . ?
C17 C16 C13 C12 -39.0(9) . . . . ?
C3 C8 C7 C6 -0.7(11) . . . . ?
C7 C8 C3 C4 0.5(10) . . . . ?
C7 C8 C3 C2 179.2(6) . . . . ?
C8 C3 C2 C1 -92.0(8) . . . . ?
C4 C3 C2 C1 86.7(8) . . . . ?
O1 C1 C2 C3 -89.0(7) . . . . ?
O2 C1 C2 C3 86.6(7) . . . . ?
C8 C3 C4 C5 -0.3(10) . . . . ?
C2 C3 C4 C5 -179.0(6) . . . . ?
C6 C5 C4 C3 0.3(11) . . . . ?
C4 C5 C6 C7 -0.4(11) . . . . ?
C4 C5 C6 C9 -176.8(7) . . . . ?
C8 C7 C6 C5 0.7(11) . . . . ?
C8 C7 C6 C9 177.1(7) . . . . ?
C10 C9 C6 C5 -137.4(7) . . . . ?
C10 C9 C6 C7 46.3(9) . . . . ?
C15 N1 C11 C12 0.3(10) . . . . ?
Zn1 N1 C11 C12 176.0(5) . . . . ?
C13 C12 C11 N1 -1.6(11) . . . . ?
Zn1 O3 C10 O4 6.2(6) 1_565 . . . ?
Zn1 O3 C10 C9 -174.5(5) 1_565 . . . ?
Zn1 O4 C10 O3 -6.6(6) 1_565 . . . ?
Zn1 O4 C10 C9 174.1(5) 1_565 . . . ?
C6 C9 C10 O3 63.1(8) . . . . ?
C6 C9 C10 O4 -117.6(7) . . . . ?
C6 C9 C10 Zn1 -61(5) . . . 1_565 ?

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
O5 H5A O4 0.82 1.96 2.732(7) 157.7 1_445

_diffrn_measured_fraction_theta_max 0.959
_diffrn_reflns_theta_full        25.10
_diffrn_measured_fraction_theta_full 0.959
_refine_diff_density_max         1.178
_refine_diff_density_min         -0.413
_refine_diff_density_rms         0.118

