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

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#                                CCDC 
# 
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# 
#  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.
#
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#  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
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#  data retrieval see:
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#  from this site to visualise CIF-encoded structures and 
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data_sdl239

_audit_creation_method           SHELXL-97
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_formula_moiety         'C20 H17 N3 Ni O6'
_chemical_formula_sum            'C20 H17 N3 Ni O6'
_chemical_melting_point          ?

_exptl_crystal_description       block
_exptl_crystal_colour            green

_diffrn_ambient_temperature      150(2)
_chemical_formula_weight         454.08

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'
Ni Ni 0.3393 1.1124 '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'

_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_H-M   'F d d 2'
_symmetry_space_group_name_Hall  'F 2 -2d'
_symmetry_int_tables_number      43
_chemical_absolute_configuration ?

loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, z'
'-x+1/4, y+1/4, z+1/4'
'x+3/4, -y+3/4, z+1/4'
'x, y+1/2, z+1/2'
'-x, -y+1/2, z+1/2'
'-x+1/4, y+3/4, z+3/4'
'x+3/4, -y+5/4, z+3/4'
'x+1/2, y, z+1/2'
'-x+1/2, -y, z+1/2'
'-x+3/4, y+1/4, z+3/4'
'x+5/4, -y+3/4, z+3/4'
'x+1/2, y+1/2, z'
'-x+1/2, -y+1/2, z'
'-x+3/4, y+3/4, z+1/4'
'x+5/4, -y+5/4, z+1/4'

_cell_length_a                   17.297(2)
_cell_length_b                   30.446(4)
_cell_length_c                   14.7303(19)
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_volume                     7757.3(17)
_cell_formula_units_Z            16
_cell_measurement_temperature    150(2)
_cell_measurement_reflns_used    8042
_cell_measurement_theta_min      2.7
_cell_measurement_theta_max      27.2
_exptl_crystal_size_max          0.31
_exptl_crystal_size_mid          0.29
_exptl_crystal_size_min          0.28
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.555
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             3744
_exptl_absorpt_coefficient_mu    1.045
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.7385
_exptl_absorpt_correction_T_max  0.7600
_exptl_absorpt_process_details   'SADABS (Sheldrick, 2003)'

_exptl_special_details           
; 
 ? 
;
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Bruker SMART APEXII'
_diffrn_measurement_method       ω
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            25207
_diffrn_reflns_av_R_equivalents  0.0751
_diffrn_reflns_av_unetI/netI     0.0605
_diffrn_reflns_limit_h_min       -23
_diffrn_reflns_limit_h_max       23
_diffrn_reflns_limit_k_min       -41
_diffrn_reflns_limit_k_max       41
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_theta_min         1.94
_diffrn_reflns_theta_max         28.74
_reflns_number_total             5007
_reflns_number_gt                4300
_reflns_threshold_expression     I>2σ

_computing_data_collection       'APEX2 (Bruker, 2007)'
_computing_cell_refinement       'SAINT (Bruker, 2007)'
_computing_data_reduction        'SAINT (Bruker, 2007)'
_computing_structure_solution    'SHELXTL (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXTL (Sheldrick, 2008)'
_computing_molecular_graphics    'SHELXTL (Sheldrick, 2008)'
_computing_publication_material  'DIAMOND (Brandenburg, 2006)'

_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)+(0.1043P)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     SHELXL
_refine_ls_extinction_coef       0.00067(13)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0.75(2)
_refine_ls_number_reflns         5007
_refine_ls_number_parameters     281
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0733
_refine_ls_R_factor_gt           0.0684
_refine_ls_wR_factor_ref         0.1824
_refine_ls_wR_factor_gt          0.1784
_refine_ls_goodness_of_fit_ref   1.165
_refine_ls_restrained_S_all      1.165
_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
C11 C 0.5950(3) 0.25281(17) 0.8011(3) 0.0331(9) Uani 1 1 d . . .
Ni1 Ni 0.52435(3) 0.155824(18) 0.60023(4) 0.02918(18) Uani 1 1 d . . .
O1 O 0.43783(19) 0.15326(11) 0.6946(2) 0.0327(7) Uani 1 1 d . . .
O2 O 0.33762(19) 0.12592(12) 0.6159(2) 0.0358(7) Uani 1 1 d . . .
O3 O 0.4713(2) 0.10313(13) 0.5307(3) 0.0327(8) Uani 1 1 d . . .
H3 H 0.4254 0.1020 0.5442 0.049 Uiso 1 1 d R . .
O4 O 0.5756(2) 0.10672(13) 0.6794(2) 0.0350(7) Uani 1 1 d . . .
H4A H 0.5723 0.1134 0.7332 0.052 Uiso 1 1 d R . .
O5 O 0.21760(19) 0.14294(13) 1.0916(3) 0.0410(8) Uani 1 1 d . . .
O6 O 0.1099(2) 0.14992(12) 1.0061(3) 0.0371(8) Uani 1 1 d . . .
N1 N 0.5792(2) 0.20706(14) 0.6702(3) 0.0314(8) Uani 1 1 d . . .
N2 N 0.3901(2) 0.25439(14) 0.4709(3) 0.0340(8) Uani 1 1 d . . .
N3 N 0.4704(2) 0.20291(15) 0.5220(3) 0.0322(8) Uani 1 1 d . . .
C1 C 0.4746(3) 0.20512(17) 0.4292(3) 0.0328(10) Uani 1 1 d . . .
H1 H 0.5074 0.1873 0.3929 0.039 Uiso 1 1 calc R . .
C2 C 0.4254(3) 0.23647(16) 0.3958(3) 0.0324(9) Uani 1 1 d . . .
C3 C 0.4192(3) 0.23354(16) 0.5473(3) 0.0333(9) Uani 1 1 d . . .
C4 C 0.3941(3) 0.24683(17) 0.6337(3) 0.0372(10) Uani 1 1 d . . .
H4 H 0.4139 0.2332 0.6869 0.045 Uiso 1 1 calc R . .
C5 C 0.3404(3) 0.27999(19) 0.6396(4) 0.0440(12) Uani 1 1 d . . .
H5 H 0.3237 0.2899 0.6975 0.053 Uiso 1 1 calc R . .
C6 C 0.3098(3) 0.29936(19) 0.5603(4) 0.0447(12) Uani 1 1 d . . .
H6 H 0.2716 0.3216 0.5655 0.054 Uiso 1 1 calc R . .
C7 C 0.3339(3) 0.28685(17) 0.4772(4) 0.0376(10) Uani 1 1 d . . .
H7 H 0.3130 0.3000 0.4241 0.045 Uiso 1 1 calc R . .
C8 C 0.6233(3) 0.23541(17) 0.6231(3) 0.0357(10) Uani 1 1 d . . .
H8 H 0.6324 0.2296 0.5607 0.043 Uiso 1 1 calc R . .
C9 C 0.6558(3) 0.27235(18) 0.6610(4) 0.0404(11) Uani 1 1 d . . .
H9 H 0.6872 0.2914 0.6257 0.048 Uiso 1 1 calc R . .
C10 C 0.6417(3) 0.28109(18) 0.7516(4) 0.0389(11) Uani 1 1 d . . .
H10 H 0.6637 0.3062 0.7797 0.047 Uiso 1 1 calc R . .
C12 C 0.5658(3) 0.21585(16) 0.7586(3) 0.0330(9) Uani 1 1 d . . .
H12 H 0.5353 0.1959 0.7929 0.040 Uiso 1 1 calc R . .
C13 C 0.3193(3) 0.14430(19) 0.7717(3) 0.0327(9) Uani 1 1 d . . .
C14 C 0.3678(3) 0.14107(16) 0.6873(3) 0.0306(9) Uani 1 1 d . . .
C15 C 0.3501(3) 0.15984(18) 0.8515(4) 0.0396(10) Uani 1 1 d . . .
H15 H 0.4016 0.1707 0.8521 0.047 Uiso 1 1 calc R . .
C16 C 0.3070(3) 0.1599(2) 0.9317(3) 0.0405(12) Uani 1 1 d . . .
H16 H 0.3298 0.1693 0.9870 0.049 Uiso 1 1 calc R . .
C17 C 0.2302(3) 0.1460(2) 0.9300(3) 0.0342(11) Uani 1 1 d . . .
C18 C 0.1973(3) 0.13280(18) 0.8494(4) 0.0394(11) Uani 1 1 d . . .
H18 H 0.1441 0.1250 0.8473 0.047 Uiso 1 1 calc R . .
C19 C 0.2420(3) 0.1309(2) 0.7706(3) 0.0396(11) Uani 1 1 d . . .
H19 H 0.2198 0.1203 0.7158 0.047 Uiso 1 1 calc R . .
C20 C 0.1825(3) 0.14638(16) 1.0164(3) 0.0329(9) Uani 1 1 d . . .
H4B H 0.626(4) 0.112(2) 0.655(5) 0.056(19) Uiso 1 1 d . . .
H3B H 0.472(5) 0.100(3) 0.474(7) 0.08(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
C11 C12 1.383(7) . ?
C11 C10 1.387(7) . ?
C11 C2 1.476(6) 6_655 ?
Ni1 O6 2.036(4) 9_554 ?
Ni1 O1 2.044(3) . ?
Ni1 N3 2.062(4) . ?
Ni1 O4 2.092(4) . ?
Ni1 N1 2.097(4) . ?
Ni1 O3 2.113(4) . ?
O1 C14 1.272(6) . ?
O2 C14 1.262(6) . ?
O3 H3 0.8200 . ?
O3 H3B 0.84(10) . ?
O4 H4A 0.8200 . ?
O4 H4B 0.96(8) . ?
O5 C20 1.268(6) . ?
O6 C20 1.270(6) . ?
O6 Ni1 2.035(4) 9_455 ?
N1 C8 1.344(6) . ?
N1 C12 1.349(6) . ?
N2 C2 1.376(6) . ?
N2 C3 1.388(6) . ?
N2 C7 1.389(6) . ?
N3 C3 1.339(6) . ?
N3 C1 1.370(6) . ?
C1 C2 1.371(7) . ?
C1 H1 0.9500 . ?
C2 C11 1.476(6) 6_654 ?
C3 C4 1.404(7) . ?
C4 C5 1.375(7) . ?
C4 H4 0.9500 . ?
C5 C6 1.412(7) . ?
C5 H5 0.9500 . ?
C6 C7 1.347(8) . ?
C6 H6 0.9500 . ?
C7 H7 0.9500 . ?
C8 C9 1.376(7) . ?
C8 H8 0.9500 . ?
C9 C10 1.382(7) . ?
C9 H9 0.9500 . ?
C10 H10 0.9500 . ?
C12 H12 0.9500 . ?
C13 C15 1.374(7) . ?
C13 C19 1.398(8) . ?
C13 C14 1.503(7) . ?
C15 C16 1.397(7) . ?
C15 H15 0.9500 . ?
C16 C17 1.394(8) . ?
C16 H16 0.9500 . ?
C17 C18 1.377(7) . ?
C17 C20 1.517(7) . ?
C18 C19 1.396(7) . ?
C18 H18 0.9500 . ?
C19 H19 0.9500 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C12 C11 C10 118.7(4) . . ?
C12 C11 C2 121.4(4) . 6_655 ?
C10 C11 C2 119.9(4) . 6_655 ?
O6 Ni1 O1 172.74(14) 9_554 . ?
O6 Ni1 N3 90.54(15) 9_554 . ?
O1 Ni1 N3 94.32(14) . . ?
O6 Ni1 O4 90.51(15) 9_554 . ?
O1 Ni1 O4 84.48(14) . . ?
N3 Ni1 O4 177.99(16) . . ?
O6 Ni1 N1 94.12(15) 9_554 . ?
O1 Ni1 N1 91.45(15) . . ?
N3 Ni1 N1 87.85(16) . . ?
O4 Ni1 N1 93.78(16) . . ?
O6 Ni1 O3 85.31(14) 9_554 . ?
O1 Ni1 O3 89.02(14) . . ?
N3 Ni1 O3 93.45(16) . . ?
O4 Ni1 O3 84.92(13) . . ?
N1 Ni1 O3 178.58(16) . . ?
C14 O1 Ni1 130.7(3) . . ?
Ni1 O3 H3 109.5 . . ?
Ni1 O3 H3B 125(6) . . ?
H3 O3 H3B 104.3 . . ?
Ni1 O4 H4A 109.4 . . ?
Ni1 O4 H4B 94(4) . . ?
H4A O4 H4B 113.2 . . ?
C20 O6 Ni1 130.2(3) . 9_455 ?
C8 N1 C12 117.9(4) . . ?
C8 N1 Ni1 118.7(3) . . ?
C12 N1 Ni1 123.0(3) . . ?
C2 N2 C3 108.0(4) . . ?
C2 N2 C7 130.3(4) . . ?
C3 N2 C7 121.7(4) . . ?
C3 N3 C1 106.2(4) . . ?
C3 N3 Ni1 128.9(3) . . ?
C1 N3 Ni1 124.6(3) . . ?
N3 C1 C2 111.1(4) . . ?
N3 C1 H1 124.5 . . ?
C2 C1 H1 124.5 . . ?
C1 C2 N2 105.3(4) . . ?
C1 C2 C11 130.0(4) . 6_654 ?
N2 C2 C11 124.5(4) . 6_654 ?
N3 C3 N2 109.4(4) . . ?
N3 C3 C4 131.1(4) . . ?
N2 C3 C4 119.4(4) . . ?
C5 C4 C3 118.6(5) . . ?
C5 C4 H4 120.7 . . ?
C3 C4 H4 120.7 . . ?
C4 C5 C6 120.5(5) . . ?
C4 C5 H5 119.7 . . ?
C6 C5 H5 119.7 . . ?
C7 C6 C5 121.1(5) . . ?
C7 C6 H6 119.4 . . ?
C5 C6 H6 119.4 . . ?
C6 C7 N2 118.6(5) . . ?
C6 C7 H7 120.7 . . ?
N2 C7 H7 120.7 . . ?
N1 C8 C9 123.2(4) . . ?
N1 C8 H8 118.4 . . ?
C9 C8 H8 118.4 . . ?
C8 C9 C10 118.5(5) . . ?
C8 C9 H9 120.8 . . ?
C10 C9 H9 120.8 . . ?
C9 C10 C11 119.4(5) . . ?
C9 C10 H10 120.3 . . ?
C11 C10 H10 120.3 . . ?
N1 C12 C11 122.4(4) . . ?
N1 C12 H12 118.8 . . ?
C11 C12 H12 118.8 . . ?
C15 C13 C19 118.8(4) . . ?
C15 C13 C14 120.9(5) . . ?
C19 C13 C14 120.3(4) . . ?
O2 C14 O1 124.8(4) . . ?
O2 C14 C13 118.9(4) . . ?
O1 C14 C13 116.3(4) . . ?
C13 C15 C16 121.0(5) . . ?
C13 C15 H15 119.5 . . ?
C16 C15 H15 119.5 . . ?
C17 C16 C15 119.6(5) . . ?
C17 C16 H16 120.2 . . ?
C15 C16 H16 120.2 . . ?
C18 C17 C16 119.9(5) . . ?
C18 C17 C20 120.1(5) . . ?
C16 C17 C20 120.0(5) . . ?
C17 C18 C19 120.0(5) . . ?
C17 C18 H18 120.0 . . ?
C19 C18 H18 120.0 . . ?
C18 C19 C13 120.6(5) . . ?
C18 C19 H19 119.7 . . ?
C13 C19 H19 119.7 . . ?
O5 C20 O6 125.8(4) . . ?
O5 C20 C17 118.2(4) . . ?
O6 C20 C17 116.0(4) . . ?

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
N3 Ni1 O1 C14 64.6(4) . . . . ?
O4 Ni1 O1 C14 -113.8(4) . . . . ?
N1 Ni1 O1 C14 152.6(4) . . . . ?
O3 Ni1 O1 C14 -28.8(4) . . . . ?
O6 Ni1 N1 C8 32.1(4) 9_554 . . . ?
O1 Ni1 N1 C8 -152.6(4) . . . . ?
N3 Ni1 N1 C8 -58.3(4) . . . . ?
O4 Ni1 N1 C8 122.8(4) . . . . ?
O6 Ni1 N1 C12 -155.4(4) 9_554 . . . ?
O1 Ni1 N1 C12 20.0(4) . . . . ?
N3 Ni1 N1 C12 114.2(4) . . . . ?
O4 Ni1 N1 C12 -64.6(4) . . . . ?
O6 Ni1 N3 C3 -158.8(4) 9_554 . . . ?
O1 Ni1 N3 C3 26.6(4) . . . . ?
N1 Ni1 N3 C3 -64.7(4) . . . . ?
O3 Ni1 N3 C3 115.9(4) . . . . ?
O6 Ni1 N3 C1 29.1(4) 9_554 . . . ?
O1 Ni1 N3 C1 -145.5(4) . . . . ?
N1 Ni1 N3 C1 123.2(4) . . . . ?
O3 Ni1 N3 C1 -56.2(4) . . . . ?
C3 N3 C1 C2 -1.1(6) . . . . ?
Ni1 N3 C1 C2 172.5(3) . . . . ?
N3 C1 C2 N2 0.5(6) . . . . ?
N3 C1 C2 C11 -173.2(5) . . . 6_654 ?
C3 N2 C2 C1 0.3(5) . . . . ?
C7 N2 C2 C1 -178.6(5) . . . . ?
C3 N2 C2 C11 174.4(5) . . . 6_654 ?
C7 N2 C2 C11 -4.5(8) . . . 6_654 ?
C1 N3 C3 N2 1.2(5) . . . . ?
Ni1 N3 C3 N2 -172.0(3) . . . . ?
C1 N3 C3 C4 -177.6(6) . . . . ?
Ni1 N3 C3 C4 9.2(8) . . . . ?
C2 N2 C3 N3 -1.0(5) . . . . ?
C7 N2 C3 N3 178.1(4) . . . . ?
C2 N2 C3 C4 178.0(5) . . . . ?
C7 N2 C3 C4 -2.9(7) . . . . ?
N3 C3 C4 C5 179.5(5) . . . . ?
N2 C3 C4 C5 0.8(7) . . . . ?
C3 C4 C5 C6 1.6(9) . . . . ?
C4 C5 C6 C7 -1.9(9) . . . . ?
C5 C6 C7 N2 -0.2(9) . . . . ?
C2 N2 C7 C6 -178.6(5) . . . . ?
C3 N2 C7 C6 2.6(8) . . . . ?
C12 N1 C8 C9 0.8(7) . . . . ?
Ni1 N1 C8 C9 173.7(4) . . . . ?
N1 C8 C9 C10 -0.8(8) . . . . ?
C8 C9 C10 C11 -0.6(8) . . . . ?
C12 C11 C10 C9 1.9(7) . . . . ?
C2 C11 C10 C9 -175.3(5) 6_655 . . . ?
C8 N1 C12 C11 0.7(7) . . . . ?
Ni1 N1 C12 C11 -171.9(3) . . . . ?
C10 C11 C12 N1 -2.0(7) . . . . ?
C2 C11 C12 N1 175.1(4) 6_655 . . . ?
Ni1 O1 C14 O2 2.6(7) . . . . ?
Ni1 O1 C14 C13 -179.0(3) . . . . ?
C15 C13 C14 O2 178.8(5) . . . . ?
C19 C13 C14 O2 -0.2(8) . . . . ?
C15 C13 C14 O1 0.2(7) . . . . ?
C19 C13 C14 O1 -178.8(5) . . . . ?
C19 C13 C15 C16 3.8(9) . . . . ?
C14 C13 C15 C16 -175.2(5) . . . . ?
C13 C15 C16 C17 -3.3(9) . . . . ?
C15 C16 C17 C18 -0.6(9) . . . . ?
C15 C16 C17 C20 -179.3(5) . . . . ?
C16 C17 C18 C19 3.8(9) . . . . ?
C20 C17 C18 C19 -177.5(5) . . . . ?
C17 C18 C19 C13 -3.2(9) . . . . ?
C15 C13 C19 C18 -0.6(8) . . . . ?
C14 C13 C19 C18 178.5(5) . . . . ?
Ni1 O6 C20 O5 4.8(8) 9_455 . . . ?
Ni1 O6 C20 C17 -175.6(3) 9_455 . . . ?
C18 C17 C20 O5 154.9(5) . . . . ?
C16 C17 C20 O5 -26.3(8) . . . . ?
C18 C17 C20 O6 -24.7(8) . . . . ?
C16 C17 C20 O6 154.1(5) . . . . ?

_diffrn_measured_fraction_theta_max 0.999
_diffrn_reflns_theta_full        28.74
_diffrn_measured_fraction_theta_full 0.999
_refine_diff_density_max         1.192
_refine_diff_density_min         -1.943
_refine_diff_density_rms         0.123
_diffrn_standards_number         0
_diffrn_standards_interval_count 0
_diffrn_standards_interval_time  0
_diffrn_standards_decay_%        0

_database_code_depnum_ccdc_archive 'CCDC 998457'
#######################################################################
#
#                 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_sdl221_sqd

_audit_creation_method           SHELXL-97
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_formula_moiety         'C40 H28 N6 Ni2 O9'
_chemical_formula_sum            'C40 H28 N6 Ni2 O9'
_chemical_melting_point          ?

_exptl_crystal_description       block
_exptl_crystal_colour            blue-green

_diffrn_ambient_temperature      150(2)
_chemical_formula_weight         854.10

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'
Ni Ni 0.3393 1.1124 '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'

_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_H-M   'F d d 2'
_symmetry_int_tables_number      43
_chemical_absolute_configuration ?

loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, z'
'-x+1/4, y+1/4, z+1/4'
'x+3/4, -y+3/4, z+1/4'
'x, y+1/2, z+1/2'
'-x, -y+1/2, z+1/2'
'-x+1/4, y+3/4, z+3/4'
'x+3/4, -y+5/4, z+3/4'
'x+1/2, y, z+1/2'
'-x+1/2, -y, z+1/2'
'-x+3/4, y+1/4, z+3/4'
'x+5/4, -y+3/4, z+3/4'
'x+1/2, y+1/2, z'
'-x+1/2, -y+1/2, z'
'-x+3/4, y+3/4, z+1/4'
'x+5/4, -y+5/4, z+1/4'

_cell_length_a                   11.723(2)
_cell_length_b                   22.957(6)
_cell_length_c                   31.011(11)
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_volume                     8346(4)
_cell_formula_units_Z            8
_cell_measurement_temperature    150(2)
_cell_measurement_reflns_used    6946
_cell_measurement_theta_min      2.6
_cell_measurement_theta_max      28.6
_exptl_crystal_size_max          0.25
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.20
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.360
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             3504
_exptl_absorpt_coefficient_mu    0.961
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.7951
_exptl_absorpt_correction_T_max  0.8310
_exptl_absorpt_process_details   'SADABS (Sheldrick, 2003)'

_exptl_special_details           
; 
 ? 
;
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Bruker SMART APEXII'
_diffrn_measurement_method       ω
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            21153
_diffrn_reflns_av_R_equivalents  0.0888
_diffrn_reflns_av_unetI/netI     0.0709
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_k_min       -22
_diffrn_reflns_limit_k_max       29
_diffrn_reflns_limit_l_min       -39
_diffrn_reflns_limit_l_max       38
_diffrn_reflns_theta_min         2.06
_diffrn_reflns_theta_max         26.98
_reflns_number_total             4545
_reflns_number_gt                4273
_reflns_threshold_expression     I>2σ

_computing_data_collection       'APEX2 (Bruker, 2007)'
_computing_cell_refinement       'SAINT (Bruker, 2007)'
_computing_data_reduction        'SAINT (Bruker, 2007)'
_computing_structure_solution    'SHELXTL (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXTL (Sheldrick, 2008)'
_computing_molecular_graphics    'SHELXTL (Sheldrick, 2008)'
_computing_publication_material  'DIAMOND (Brandenburg, 2006)'

_refine_special_details          SQUEEZE

_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)+(0.0428P)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_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0.976(14)
_refine_ls_number_reflns         4545
_refine_ls_number_parameters     263
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0460
_refine_ls_R_factor_gt           0.0432
_refine_ls_wR_factor_ref         0.1076
_refine_ls_wR_factor_gt          0.1066
_refine_ls_goodness_of_fit_ref   1.142
_refine_ls_restrained_S_all      1.142
_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
C2 C 1.1017(2) 0.10986(15) 0.19889(10) 0.0321(7) Uani 1 1 d . . .
C7 C 1.0220(3) 0.13698(14) 0.17278(9) 0.0339(7) Uani 1 1 d . . .
H7 H 0.9431 0.1317 0.1786 0.041 Uiso 1 1 calc R . .
C6 C 1.0549(3) 0.17169(14) 0.13834(10) 0.0329(7) Uani 1 1 d . . .
C5 C 1.1705(3) 0.17970(16) 0.12997(12) 0.0425(8) Uani 1 1 d . . .
H5 H 1.1941 0.2040 0.1068 0.051 Uiso 1 1 calc R . .
C4 C 1.2508(3) 0.1523(2) 0.15537(13) 0.0562(11) Uani 1 1 d . . .
H4 H 1.3297 0.1574 0.1495 0.067 Uiso 1 1 calc R . .
C3 C 1.2170(3) 0.11713(19) 0.18952(13) 0.0494(10) Uani 1 1 d . . .
H3 H 1.2729 0.0979 0.2066 0.059 Uiso 1 1 calc R . .
C1 C 1.0645(3) 0.07056(14) 0.23517(9) 0.0317(6) Uani 1 1 d . . .
C14 C 0.8500(3) 0.09710(16) 0.37552(10) 0.0357(7) Uani 1 1 d . . .
H14 H 0.8333 0.0614 0.3896 0.043 Uiso 1 1 calc R . .
C15 C 0.8695(3) 0.14816(17) 0.39655(11) 0.0353(7) Uani 1 1 d . . .
C9 C 0.8789(3) 0.15876(19) 0.32498(12) 0.0467(9) Uani 1 1 d . . .
C13 C 0.9054(6) 0.2468(2) 0.36692(16) 0.0836(17) Uani 1 1 d . . .
H13 H 0.9138 0.2655 0.3941 0.100 Uiso 1 1 calc R . .
C12 C 0.9098(9) 0.2778(2) 0.3294(2) 0.133(4) Uani 1 1 d . . .
H12 H 0.9154 0.3190 0.3303 0.160 Uiso 1 1 calc R . .
C10 C 0.8874(5) 0.1909(2) 0.28690(15) 0.0705(15) Uani 1 1 d . . .
H10 H 0.8799 0.1721 0.2598 0.085 Uiso 1 1 calc R . .
C17 C 0.9624(3) 0.18291(15) 0.46503(10) 0.0334(7) Uani 1 1 d . . .
H17 H 1.0291 0.1917 0.4489 0.040 Uiso 1 1 calc R . .
C16 C 0.8675(3) 0.16128(17) 0.44288(11) 0.0371(7) Uani 1 1 d . . .
C20 C 0.7720(3) 0.14849(18) 0.46747(12) 0.0526(10) Uani 1 1 d . . .
H20 H 0.7060 0.1326 0.4541 0.063 Uiso 1 1 calc R . .
C19 C 0.7725(3) 0.1588(2) 0.51162(13) 0.0572(11) Uani 1 1 d . . .
H19 H 0.7069 0.1509 0.5286 0.069 Uiso 1 1 calc R . .
C18 C 0.8700(3) 0.18077(17) 0.53005(11) 0.0406(8) Uani 1 1 d . . .
H18 H 0.8700 0.1884 0.5602 0.049 Uiso 1 1 calc R . .
C11 C 0.9062(8) 0.2485(2) 0.28885(19) 0.131(4) Uani 1 1 d . . .
H11 H 0.9172 0.2700 0.2630 0.158 Uiso 1 1 calc R . .
C8 C 0.9660(3) 0.19976(16) 0.11109(11) 0.0371(7) Uani 1 1 d . . .
H1 H 1.034(4) 0.0356(19) 0.3394(14) 0.059(13) Uiso 1 1 d . . .
N1 N 0.9646(2) 0.19185(12) 0.50765(8) 0.0318(5) Uani 1 1 d . . .
N2 N 0.8573(2) 0.10318(14) 0.33174(9) 0.0350(6) Uani 1 1 d . . .
N3 N 0.8885(3) 0.18790(16) 0.36409(11) 0.0502(8) Uani 1 1 d . . .
Ni1 Ni 0.86108(3) 0.030400(18) 0.289898(10) 0.02788(12) Uani 1 1 d . . .
O1 O 0.96047(18) 0.07118(10) 0.24442(7) 0.0328(5) Uani 1 1 d . . .
O2 O 1.14255(18) 0.04152(12) 0.25269(8) 0.0374(5) Uani 1 1 d . . .
O3 O 0.8649(2) 0.18415(17) 0.11817(11) 0.0712(11) Uani 1 1 d . . .
O4 O 0.99575(19) 0.23687(10) 0.08345(6) 0.0325(5) Uani 1 1 d . . .
O5 O 1.0000 0.0000 0.32216(10) 0.0312(7) Uani 1 2 d S . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
C2 C7 1.384(4) . ?
C2 C3 1.393(4) . ?
C2 C1 1.507(4) . ?
C7 C6 1.387(4) . ?
C7 H7 0.9500 . ?
C6 C5 1.393(5) . ?
C6 C8 1.488(4) . ?
C5 C4 1.380(5) . ?
C5 H5 0.9500 . ?
C4 C3 1.389(5) . ?
C4 H4 0.9500 . ?
C3 H3 0.9500 . ?
C1 O1 1.253(4) . ?
C1 O2 1.256(4) . ?
C14 C15 1.361(5) . ?
C14 N2 1.368(4) . ?
C14 H14 0.9500 . ?
C15 N3 1.376(5) . ?
C15 C16 1.468(5) . ?
C9 N2 1.318(6) . ?
C9 N3 1.390(5) . ?
C9 C10 1.396(6) . ?
C13 C12 1.365(8) . ?
C13 N3 1.370(7) . ?
C13 H13 0.9500 . ?
C12 C11 1.426(9) . ?
C12 H12 0.9500 . ?
C10 C11 1.341(8) . ?
C10 H10 0.9500 . ?
C17 N1 1.338(4) . ?
C17 C16 1.399(4) . ?
C17 H17 0.9500 . ?
C16 C20 1.386(5) . ?
C20 C19 1.389(5) . ?
C20 H20 0.9500 . ?
C19 C18 1.374(5) . ?
C19 H19 0.9500 . ?
C18 N1 1.333(4) . ?
C18 H18 0.9500 . ?
C11 H11 0.9500 . ?
C8 O3 1.258(4) . ?
C8 O4 1.258(4) . ?
N1 Ni1 2.087(3) 16_445 ?
N2 Ni1 2.116(3) . ?
Ni1 O2 2.015(2) 2_755 ?
Ni1 O5 2.0348(16) . ?
Ni1 O1 2.055(2) . ?
Ni1 N1 2.087(3) 8_444 ?
Ni1 O4 2.096(2) 15_645 ?
O2 Ni1 2.015(2) 2_755 ?
O4 Ni1 2.096(2) 11_654 ?
O5 Ni1 2.0347(16) 2_755 ?
O5 H1 1.05(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
C7 C2 C3 118.6(3) . . ?
C7 C2 C1 120.7(3) . . ?
C3 C2 C1 120.6(3) . . ?
C2 C7 C6 121.4(3) . . ?
C2 C7 H7 119.3 . . ?
C6 C7 H7 119.3 . . ?
C7 C6 C5 119.3(3) . . ?
C7 C6 C8 119.4(3) . . ?
C5 C6 C8 121.2(3) . . ?
C4 C5 C6 119.8(3) . . ?
C4 C5 H5 120.1 . . ?
C6 C5 H5 120.1 . . ?
C5 C4 C3 120.4(3) . . ?
C5 C4 H4 119.8 . . ?
C3 C4 H4 119.8 . . ?
C4 C3 C2 120.4(3) . . ?
C4 C3 H3 119.8 . . ?
C2 C3 H3 119.8 . . ?
O1 C1 O2 128.0(3) . . ?
O1 C1 C2 116.5(3) . . ?
O2 C1 C2 115.5(3) . . ?
C15 C14 N2 112.2(3) . . ?
C15 C14 H14 123.9 . . ?
N2 C14 H14 123.9 . . ?
C14 C15 N3 104.3(3) . . ?
C14 C15 C16 130.0(4) . . ?
N3 C15 C16 125.6(4) . . ?
N2 C9 N3 110.0(3) . . ?
N2 C9 C10 131.3(4) . . ?
N3 C9 C10 118.5(4) . . ?
C12 C13 N3 117.7(4) . . ?
C12 C13 H13 121.1 . . ?
N3 C13 H13 121.1 . . ?
C13 C12 C11 120.4(5) . . ?
C13 C12 H12 119.8 . . ?
C11 C12 H12 119.8 . . ?
C11 C10 C9 119.7(4) . . ?
C11 C10 H10 120.2 . . ?
C9 C10 H10 120.2 . . ?
N1 C17 C16 123.7(3) . . ?
N1 C17 H17 118.2 . . ?
C16 C17 H17 118.2 . . ?
C20 C16 C17 116.6(3) . . ?
C20 C16 C15 120.5(3) . . ?
C17 C16 C15 122.7(3) . . ?
C16 C20 C19 120.2(3) . . ?
C16 C20 H20 119.9 . . ?
C19 C20 H20 119.9 . . ?
C18 C19 C20 118.4(3) . . ?
C18 C19 H19 120.8 . . ?
C20 C19 H19 120.8 . . ?
N1 C18 C19 123.1(3) . . ?
N1 C18 H18 118.5 . . ?
C19 C18 H18 118.5 . . ?
C10 C11 C12 120.6(5) . . ?
C10 C11 H11 119.7 . . ?
C12 C11 H11 119.7 . . ?
O3 C8 O4 125.0(3) . . ?
O3 C8 C6 115.9(3) . . ?
O4 C8 C6 119.1(3) . . ?
C18 N1 C17 118.0(3) . . ?
C18 N1 Ni1 119.6(2) . 16_445 ?
C17 N1 Ni1 122.4(2) . 16_445 ?
C9 N2 C14 105.6(3) . . ?
C9 N2 Ni1 131.5(2) . . ?
C14 N2 Ni1 122.0(2) . . ?
C13 N3 C15 129.1(4) . . ?
C13 N3 C9 122.9(4) . . ?
C15 N3 C9 107.8(3) . . ?
O2 Ni1 O5 91.00(8) 2_755 . ?
O2 Ni1 O1 89.56(10) 2_755 . ?
O5 Ni1 O1 92.29(9) . . ?
O2 Ni1 N1 87.62(10) 2_755 8_444 ?
O5 Ni1 N1 177.38(8) . 8_444 ?
O1 Ni1 N1 89.92(9) . 8_444 ?
O2 Ni1 O4 88.04(10) 2_755 15_645 ?
O5 Ni1 O4 89.87(8) . 15_645 ?
O1 Ni1 O4 176.79(9) . 15_645 ?
N1 Ni1 O4 87.86(9) 8_444 15_645 ?
O2 Ni1 N2 176.23(11) 2_755 . ?
O5 Ni1 N2 89.21(9) . . ?
O1 Ni1 N2 94.19(10) . . ?
N1 Ni1 N2 92.02(10) 8_444 . ?
O4 Ni1 N2 88.20(10) 15_645 . ?
C1 O1 Ni1 134.7(2) . . ?
C1 O2 Ni1 131.9(2) . 2_755 ?
C8 O4 Ni1 126.6(2) . 11_654 ?
Ni1 O5 Ni1 121.09(15) 2_755 . ?
Ni1 O5 H1 102(3) 2_755 . ?
Ni1 O5 H1 107(3) . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C3 C2 C7 C6 -1.2(5) . . . . ?
C1 C2 C7 C6 -177.8(3) . . . . ?
C2 C7 C6 C5 -0.3(5) . . . . ?
C2 C7 C6 C8 179.8(3) . . . . ?
C7 C6 C5 C4 1.3(6) . . . . ?
C8 C6 C5 C4 -178.9(4) . . . . ?
C6 C5 C4 C3 -0.6(7) . . . . ?
C5 C4 C3 C2 -0.9(7) . . . . ?
C7 C2 C3 C4 1.8(6) . . . . ?
C1 C2 C3 C4 178.4(4) . . . . ?
C7 C2 C1 O1 -10.8(5) . . . . ?
C3 C2 C1 O1 172.7(3) . . . . ?
C7 C2 C1 O2 169.8(3) . . . . ?
C3 C2 C1 O2 -6.7(5) . . . . ?
N2 C14 C15 N3 0.7(4) . . . . ?
N2 C14 C15 C16 178.5(3) . . . . ?
N3 C13 C12 C11 -5.0(13) . . . . ?
N2 C9 C10 C11 177.4(6) . . . . ?
N3 C9 C10 C11 1.0(8) . . . . ?
N1 C17 C16 C20 -0.4(5) . . . . ?
N1 C17 C16 C15 -175.8(4) . . . . ?
C14 C15 C16 C20 -54.7(6) . . . . ?
N3 C15 C16 C20 122.6(4) . . . . ?
C14 C15 C16 C17 120.5(4) . . . . ?
N3 C15 C16 C17 -62.1(5) . . . . ?
C17 C16 C20 C19 1.9(6) . . . . ?
C15 C16 C20 C19 177.4(4) . . . . ?
C16 C20 C19 C18 -1.2(7) . . . . ?
C20 C19 C18 N1 -0.9(7) . . . . ?
C9 C10 C11 C12 -4.3(12) . . . . ?
C13 C12 C11 C10 6.5(14) . . . . ?
C7 C6 C8 O3 -8.4(5) . . . . ?
C5 C6 C8 O3 171.7(4) . . . . ?
C7 C6 C8 O4 171.1(3) . . . . ?
C5 C6 C8 O4 -8.8(5) . . . . ?
C19 C18 N1 C17 2.3(6) . . . . ?
C19 C18 N1 Ni1 -175.7(3) . . . 16_445 ?
C16 C17 N1 C18 -1.6(5) . . . . ?
C16 C17 N1 Ni1 176.4(3) . . . 16_445 ?
N3 C9 N2 C14 1.6(4) . . . . ?
C10 C9 N2 C14 -175.0(5) . . . . ?
N3 C9 N2 Ni1 -167.4(2) . . . . ?
C10 C9 N2 Ni1 16.0(7) . . . . ?
C15 C14 N2 C9 -1.4(4) . . . . ?
C15 C14 N2 Ni1 168.8(2) . . . . ?
C12 C13 N3 C15 -172.8(6) . . . . ?
C12 C13 N3 C9 1.8(9) . . . . ?
C14 C15 N3 C13 175.5(5) . . . . ?
C16 C15 N3 C13 -2.4(6) . . . . ?
C14 C15 N3 C9 0.3(4) . . . . ?
C16 C15 N3 C9 -177.6(3) . . . . ?
N2 C9 N3 C13 -176.8(4) . . . . ?
C10 C9 N3 C13 0.3(7) . . . . ?
N2 C9 N3 C15 -1.2(4) . . . . ?
C10 C9 N3 C15 175.9(4) . . . . ?
C9 N2 Ni1 O5 110.8(3) . . . . ?
C14 N2 Ni1 O5 -56.7(2) . . . . ?
C9 N2 Ni1 O1 18.5(3) . . . . ?
C14 N2 Ni1 O1 -148.9(2) . . . . ?
C9 N2 Ni1 N1 -71.5(3) . . . 8_444 ?
C14 N2 Ni1 N1 121.0(2) . . . 8_444 ?
C9 N2 Ni1 O4 -159.3(3) . . . 15_645 ?
C14 N2 Ni1 O4 33.2(2) . . . 15_645 ?
O2 C1 O1 Ni1 1.0(5) . . . . ?
C2 C1 O1 Ni1 -178.3(2) . . . . ?
O2 Ni1 O1 C1 -80.7(3) 2_755 . . . ?
O5 Ni1 O1 C1 10.3(3) . . . . ?
N1 Ni1 O1 C1 -168.3(3) 8_444 . . . ?
N2 Ni1 O1 C1 99.6(3) . . . . ?
O1 C1 O2 Ni1 19.2(5) . . . 2_755 ?
C2 C1 O2 Ni1 -161.5(2) . . . 2_755 ?
O3 C8 O4 Ni1 -2.8(6) . . . 11_654 ?
C6 C8 O4 Ni1 177.8(2) . . . 11_654 ?
O2 Ni1 O5 Ni1 49.61(7) 2_755 . . 2_755 ?
O1 Ni1 O5 Ni1 -39.98(7) . . . 2_755 ?
O4 Ni1 O5 Ni1 137.65(6) 15_645 . . 2_755 ?
N2 Ni1 O5 Ni1 -134.15(8) . . . 2_755 ?

_diffrn_measured_fraction_theta_max 1.000
_diffrn_reflns_theta_full        26.98
_diffrn_measured_fraction_theta_full 1.000
_refine_diff_density_max         0.359
_refine_diff_density_min         -0.659
_refine_diff_density_rms         0.065
_diffrn_standards_number         0
_diffrn_standards_interval_count 0
_diffrn_standards_interval_time  0
_diffrn_standards_decay_%        0

_database_code_depnum_ccdc_archive 'CCDC 998458'
#######################################################################
#
#                 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_sdl178

_audit_creation_method           SHELXL-97
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_formula_moiety         'C24 H16 N3 O7 Zn2'
_chemical_formula_sum            'C24 H16 N3 O7 Zn2'
_chemical_melting_point          ?

_exptl_crystal_description       block
_exptl_crystal_colour            orange-yellow

_diffrn_ambient_temperature      150(2)
_chemical_formula_weight         589.14

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'
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_int_tables_number      2
_chemical_absolute_configuration ?

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

_cell_length_a                   10.4229(5)
_cell_length_b                   10.5611(6)
_cell_length_c                   12.2119(6)
_cell_angle_alpha                114.782(3)
_cell_angle_beta                 109.889(4)
_cell_angle_gamma                96.087(3)
_cell_volume                     1097.91(10)
_cell_formula_units_Z            2
_cell_measurement_temperature    150(2)
_cell_measurement_reflns_used    6377
_cell_measurement_theta_min      2.6
_cell_measurement_theta_max      28.6
_exptl_crystal_size_max          0.40
_exptl_crystal_size_mid          0.30
_exptl_crystal_size_min          0.29
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.782
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             594
_exptl_absorpt_coefficient_mu    2.239
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.4663
_exptl_absorpt_correction_T_max  0.5658
_exptl_absorpt_process_details   'SADABS (Sheldrick, 2003)'

_exptl_special_details           
; 
 ? 
;
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Bruker SMART APEXII'
_diffrn_measurement_method       ω
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            13847
_diffrn_reflns_av_R_equivalents  0.0478
_diffrn_reflns_av_unetI/netI     0.1181
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_theta_min         2.16
_diffrn_reflns_theta_max         27.00
_reflns_number_total             4795
_reflns_number_gt                4209
_reflns_threshold_expression     I>2σ

_computing_data_collection       'APEX2 (Bruker, 2007)'
_computing_cell_refinement       'SAINT (Bruker, 2007)'
_computing_data_reduction        'SAINT (Bruker, 2007)'
_computing_structure_solution    'SHELXTL (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXTL (Sheldrick, 2008)'
_computing_molecular_graphics    'SHELXTL (Sheldrick, 2008)'
_computing_publication_material  'DIAMOND (Brandenburg, 2006)'

_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)+(0.0000P)²+0.4939P] 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       0.009(2)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_number_reflns         4795
_refine_ls_number_parameters     326
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0583
_refine_ls_R_factor_gt           0.0537
_refine_ls_wR_factor_ref         0.1533
_refine_ls_wR_factor_gt          0.1472
_refine_ls_goodness_of_fit_ref   1.106
_refine_ls_restrained_S_all      1.106
_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
C1 C 1.0452(4) 0.6439(4) 0.4375(4) 0.0358(8) Uani 1 1 d . . .
H1 H 1.0727 0.7068 0.5296 0.043 Uiso 1 1 calc R . .
C2 C 1.0861(4) 0.5180(4) 0.3995(4) 0.0395(9) Uani 1 1 d . . .
H2 H 1.1419 0.4956 0.4648 0.047 Uiso 1 1 calc R . .
C3 C 1.0459(4) 0.4256(4) 0.2671(4) 0.0355(8) Uani 1 1 d . . .
H3 H 1.0722 0.3378 0.2403 0.043 Uiso 1 1 calc R . .
C4 C 0.9661(4) 0.4602(4) 0.1715(3) 0.0277(7) Uani 1 1 d . . .
C5 C 0.9301(4) 0.5899(3) 0.2181(3) 0.0269(7) Uani 1 1 d . . .
H5 H 0.8763 0.6162 0.1551 0.032 Uiso 1 1 calc R . .
C6 C 0.9287(4) 0.3599(4) 0.0320(3) 0.0269(7) Uani 1 1 d . . .
C7 C 0.9916(4) 0.2559(4) -0.0161(3) 0.0289(7) Uani 1 1 d . . .
H7 H 1.0715 0.2404 0.0381 0.035 Uiso 1 1 calc R . .
C8 C 0.8190(3) 0.2300(4) -0.1923(3) 0.0273(7) Uani 1 1 d . . .
C9 C 0.7196(4) 0.1886(4) -0.3210(4) 0.0333(8) Uani 1 1 d . . .
H9 H 0.7232 0.1134 -0.3968 0.040 Uiso 1 1 calc R . .
C10 C 0.6174(4) 0.2585(4) -0.3353(4) 0.0372(8) Uani 1 1 d . . .
H10 H 0.5497 0.2332 -0.4218 0.045 Uiso 1 1 calc R . .
C11 C 0.6120(4) 0.3688(4) -0.2212(4) 0.0378(8) Uani 1 1 d . . .
H11 H 0.5386 0.4148 -0.2322 0.045 Uiso 1 1 calc R . .
C12 C 0.7089(4) 0.4096(4) -0.0974(4) 0.0313(7) Uani 1 1 d . . .
H12 H 0.7037 0.4835 -0.0218 0.038 Uiso 1 1 calc R . .
C13 C 0.6566(4) 0.8627(4) 0.2528(4) 0.0323(7) Uani 1 1 d . . .
C14 C 0.5341(3) 0.8746(4) 0.1519(4) 0.0294(7) Uani 1 1 d . . .
C15 C 0.4998(4) 0.7921(4) 0.0166(4) 0.0347(8) Uani 1 1 d . . .
H15 H 0.5530 0.7276 -0.0114 0.042 Uiso 1 1 calc R . .
C16 C 0.3884(4) 0.8035(4) -0.0773(4) 0.0341(8) Uani 1 1 d . . .
H16 H 0.3669 0.7482 -0.1693 0.041 Uiso 1 1 calc R . .
C17 C 0.3077(4) 0.8958(4) -0.0379(3) 0.0288(7) Uani 1 1 d . . .
C18 C 0.3405(4) 0.9758(4) 0.0971(4) 0.0293(7) Uani 1 1 d . . .
H18 H 0.2845 1.0370 0.1247 0.035 Uiso 1 1 calc R . .
C19 C 0.4541(4) 0.9674(4) 0.1919(4) 0.0308(7) Uani 1 1 d . . .
H19 H 0.4773 1.0248 0.2840 0.037 Uiso 1 1 calc R . .
C20 C 0.1905(4) 0.9086(4) -0.1410(4) 0.0312(7) Uani 1 1 d . . .
C21 C 0.7286(4) 0.7304(3) 0.5534(3) 0.0267(7) Uani 1 1 d . . .
C22 C 0.6111(4) 0.6111(3) 0.5275(3) 0.0272(7) Uani 1 1 d . . .
C23 C 0.5572(4) 0.4785(4) 0.4084(3) 0.0291(7) Uani 1 1 d . . .
H23 H 0.5961 0.4637 0.3456 0.035 Uiso 1 1 calc R . .
C24 C 0.5529(4) 0.6309(4) 0.6177(4) 0.0303(7) Uani 1 1 d . . .
H24 H 0.5889 0.7207 0.6985 0.036 Uiso 1 1 calc R . .
N1 N 0.9681(3) 0.6800(3) 0.3486(3) 0.0271(6) Uani 1 1 d . . .
N2 N 0.9257(3) 0.1766(3) -0.1520(3) 0.0280(6) Uani 1 1 d . . .
N3 N 0.8162(3) 0.3429(3) -0.0813(3) 0.0270(6) Uani 1 1 d . . .
O1 O 0.7175(3) 0.7675(3) 0.2113(3) 0.0356(6) Uani 1 1 d . . .
O2 O 0.6983(3) 0.9475(3) 0.3755(3) 0.0353(6) Uani 1 1 d . . .
O3 O 0.1728(3) 0.8450(3) -0.2583(3) 0.0452(7) Uani 1 1 d . . .
O4 O 0.1128(3) 0.9876(3) -0.1017(3) 0.0347(6) Uani 1 1 d . . .
O5 O 0.7571(3) 0.7161(3) 0.4582(2) 0.0339(5) Uani 1 1 d . . .
O6 O 0.7899(3) 0.8357(3) 0.6717(2) 0.0339(5) Uani 1 1 d . . .
O7 O 0.9843(2) 1.0194(2) 0.3947(2) 0.0262(5) Uani 1 1 d . . .
Zn1 Zn 0.87353(4) 0.84696(4) 0.41137(4) 0.02492(16) Uani 1 1 d . . .
Zn2 Zn 0.96635(4) 0.99234(4) 0.74884(4) 0.02562(16) Uani 1 1 d . . .
H7A H 0.9223 1.0472 0.3779 0.035 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
C1 N1 1.338(4) . ?
C1 C2 1.379(5) . ?
C1 H1 0.9500 . ?
C2 C3 1.367(5) . ?
C2 H2 0.9500 . ?
C3 C4 1.397(5) . ?
C3 H3 0.9500 . ?
C4 C5 1.394(4) . ?
C4 C6 1.457(5) . ?
C5 N1 1.349(4) . ?
C5 H5 0.9500 . ?
C6 C7 1.363(4) . ?
C6 N3 1.401(4) . ?
C7 N2 1.365(4) . ?
C7 H7 0.9500 . ?
C8 N2 1.338(4) . ?
C8 N3 1.393(4) . ?
C8 C9 1.398(5) . ?
C9 C10 1.364(5) . ?
C9 H9 0.9500 . ?
C10 C11 1.417(5) . ?
C10 H10 0.9500 . ?
C11 C12 1.347(5) . ?
C11 H11 0.9500 . ?
C12 N3 1.386(4) . ?
C12 H12 0.9500 . ?
C13 O2 1.259(4) . ?
C13 O1 1.264(4) . ?
C13 C14 1.502(5) . ?
C13 Zn1 2.502(4) . ?
C14 C15 1.393(5) . ?
C14 C19 1.395(4) . ?
C15 C16 1.385(5) . ?
C15 H15 0.9500 . ?
C16 C17 1.395(4) . ?
C16 H16 0.9500 . ?
C17 C18 1.391(5) . ?
C17 C20 1.493(5) . ?
C18 C19 1.388(5) . ?
C18 H18 0.9500 . ?
C19 H19 0.9500 . ?
C20 O3 1.235(4) . ?
C20 O4 1.285(4) . ?
C21 O5 1.249(4) . ?
C21 O6 1.267(4) . ?
C21 C22 1.504(5) . ?
C22 C24 1.383(5) . ?
C22 C23 1.401(5) . ?
C23 C24 1.383(5) 2_666 ?
C23 H23 0.9500 . ?
C24 C23 1.383(5) 2_666 ?
C24 H24 0.9500 . ?
N1 Zn1 2.102(3) . ?
N2 Zn2 1.995(3) 1_544 ?
O1 Zn1 2.146(3) . ?
O2 Zn1 2.217(2) . ?
O4 Zn2 1.965(2) 1_454 ?
O5 Zn1 2.118(2) . ?
O6 Zn2 1.968(2) . ?
O7 Zn2 1.949(2) 2_776 ?
O7 Zn1 2.040(2) 2_776 ?
O7 Zn1 2.171(2) . ?
O7 H7A 0.7387 . ?
Zn1 O7 2.040(2) 2_776 ?
Zn2 O7 1.949(2) 2_776 ?
Zn2 O4 1.965(3) 1_656 ?
Zn2 N2 1.995(3) 1_566 ?

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
N1 C1 C2 122.0(4) . . ?
N1 C1 H1 119.0 . . ?
C2 C1 H1 119.0 . . ?
C3 C2 C1 119.6(4) . . ?
C3 C2 H2 120.2 . . ?
C1 C2 H2 120.2 . . ?
C2 C3 C4 120.0(3) . . ?
C2 C3 H3 120.0 . . ?
C4 C3 H3 120.0 . . ?
C5 C4 C3 116.8(3) . . ?
C5 C4 C6 125.2(3) . . ?
C3 C4 C6 118.0(3) . . ?
N1 C5 C4 123.1(3) . . ?
N1 C5 H5 118.4 . . ?
C4 C5 H5 118.4 . . ?
C7 C6 N3 104.9(3) . . ?
C7 C6 C4 126.9(3) . . ?
N3 C6 C4 128.1(3) . . ?
C6 C7 N2 111.6(3) . . ?
C6 C7 H7 124.2 . . ?
N2 C7 H7 124.2 . . ?
N2 C8 N3 109.2(3) . . ?
N2 C8 C9 130.0(3) . . ?
N3 C8 C9 120.8(3) . . ?
C10 C9 C8 118.5(3) . . ?
C10 C9 H9 120.7 . . ?
C8 C9 H9 120.7 . . ?
C9 C10 C11 120.1(4) . . ?
C9 C10 H10 120.0 . . ?
C11 C10 H10 120.0 . . ?
C12 C11 C10 121.2(3) . . ?
C12 C11 H11 119.4 . . ?
C10 C11 H11 119.4 . . ?
C11 C12 N3 119.4(3) . . ?
C11 C12 H12 120.3 . . ?
N3 C12 H12 120.3 . . ?
O2 C13 O1 121.2(3) . . ?
O2 C13 C14 120.4(3) . . ?
O1 C13 C14 118.4(3) . . ?
O2 C13 Zn1 62.26(18) . . ?
O1 C13 Zn1 59.04(18) . . ?
C14 C13 Zn1 175.0(2) . . ?
C15 C14 C19 119.4(3) . . ?
C15 C14 C13 119.8(3) . . ?
C19 C14 C13 120.7(3) . . ?
C16 C15 C14 120.4(3) . . ?
C16 C15 H15 119.8 . . ?
C14 C15 H15 119.8 . . ?
C15 C16 C17 120.4(3) . . ?
C15 C16 H16 119.8 . . ?
C17 C16 H16 119.8 . . ?
C18 C17 C16 119.0(3) . . ?
C18 C17 C20 121.7(3) . . ?
C16 C17 C20 119.3(3) . . ?
C17 C18 C19 120.8(3) . . ?
C17 C18 H18 119.6 . . ?
C19 C18 H18 119.6 . . ?
C18 C19 C14 119.9(3) . . ?
C18 C19 H19 120.0 . . ?
C14 C19 H19 120.0 . . ?
O3 C20 O4 123.2(3) . . ?
O3 C20 C17 119.4(3) . . ?
O4 C20 C17 117.4(3) . . ?
O5 C21 O6 126.5(3) . . ?
O5 C21 C22 117.7(3) . . ?
C24 C22 C23 119.2(3) . . ?
C24 C22 C21 121.3(3) . . ?
C23 C22 C21 119.4(3) . . ?
C24 C23 C22 119.9(3) 2_666 . ?
C24 C23 H23 120.0 2_666 . ?
C22 C23 H23 120.0 . . ?
C22 C24 C23 120.8(3) . 2_666 ?
C22 C24 H24 119.6 . . ?
C23 C24 H24 119.6 2_666 . ?
C1 N1 C5 118.5(3) . . ?
C1 N1 Zn1 118.6(2) . . ?
C5 N1 Zn1 121.5(2) . . ?
C8 N2 C7 106.8(3) . . ?
C8 N2 Zn2 130.4(2) . 1_544 ?
C7 N2 Zn2 121.4(2) . 1_544 ?
C12 N3 C8 119.9(3) . . ?
C12 N3 C6 132.5(3) . . ?
C8 N3 C6 107.5(3) . . ?
C13 O1 Zn1 90.6(2) . . ?
C13 O2 Zn1 87.6(2) . . ?
C20 O4 Zn2 111.3(2) . 1_454 ?
C21 O5 Zn1 138.1(2) . . ?
C21 O6 Zn2 126.9(2) . . ?
Zn2 O7 Zn1 120.05(11) 2_776 2_776 ?
Zn2 O7 Zn1 129.51(11) 2_776 . ?
Zn1 O7 Zn1 100.74(10) 2_776 . ?
Zn2 O7 H7A 97.1 2_776 . ?
Zn1 O7 H7A 110.4 2_776 . ?
Zn1 O7 H7A 94.9 . . ?
O7 Zn1 N1 102.35(10) 2_776 . ?
O7 Zn1 O5 93.62(9) 2_776 . ?
N1 Zn1 O5 87.55(10) . . ?
O7 Zn1 O1 162.87(9) 2_776 . ?
N1 Zn1 O1 91.87(10) . . ?
O5 Zn1 O1 96.52(10) . . ?
O7 Zn1 O7 79.26(10) 2_776 . ?
N1 Zn1 O7 103.78(10) . . ?
O5 Zn1 O7 167.62(9) . . ?
O1 Zn1 O7 88.18(9) . . ?
O7 Zn1 O2 105.94(9) 2_776 . ?
N1 Zn1 O2 151.68(11) . . ?
O5 Zn1 O2 89.60(10) . . ?
O1 Zn1 O2 60.48(9) . . ?
O7 Zn1 O2 82.74(9) . . ?
O7 Zn1 C13 135.02(10) 2_776 . ?
N1 Zn1 C13 122.12(12) . . ?
O5 Zn1 C13 94.59(11) . . ?
O1 Zn1 C13 30.34(10) . . ?
O7 Zn1 C13 83.67(10) . . ?
O2 Zn1 C13 30.17(10) . . ?
O7 Zn2 O4 116.94(10) 2_776 1_656 ?
O7 Zn2 O6 108.53(10) 2_776 . ?
O4 Zn2 O6 109.80(11) 1_656 . ?
O7 Zn2 N2 115.35(10) 2_776 1_566 ?
O4 Zn2 N2 100.01(11) 1_656 1_566 ?
O6 Zn2 N2 105.46(11) . 1_566 ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
N1 C1 C2 C3 -0.8(7) . . . . ?
C1 C2 C3 C4 1.2(7) . . . . ?
C2 C3 C4 C5 -0.6(6) . . . . ?
C2 C3 C4 C6 178.6(4) . . . . ?
C3 C4 C5 N1 -0.3(5) . . . . ?
C6 C4 C5 N1 -179.5(3) . . . . ?
C5 C4 C6 C7 160.5(3) . . . . ?
C3 C4 C6 C7 -18.7(6) . . . . ?
C5 C4 C6 N3 -23.5(6) . . . . ?
C3 C4 C6 N3 157.3(3) . . . . ?
N3 C6 C7 N2 0.5(4) . . . . ?
C4 C6 C7 N2 177.2(3) . . . . ?
N2 C8 C9 C10 178.1(4) . . . . ?
N3 C8 C9 C10 -1.8(5) . . . . ?
C8 C9 C10 C11 -1.0(6) . . . . ?
C9 C10 C11 C12 1.8(6) . . . . ?
C10 C11 C12 N3 0.2(6) . . . . ?
O2 C13 C14 C15 172.5(3) . . . . ?
O1 C13 C14 C15 -6.4(5) . . . . ?
O2 C13 C14 C19 -7.5(5) . . . . ?
O1 C13 C14 C19 173.6(3) . . . . ?
C19 C14 C15 C16 0.9(6) . . . . ?
C13 C14 C15 C16 -179.1(3) . . . . ?
C14 C15 C16 C17 -1.2(6) . . . . ?
C15 C16 C17 C18 -0.1(6) . . . . ?
C15 C16 C17 C20 178.6(3) . . . . ?
C16 C17 C18 C19 1.6(5) . . . . ?
C20 C17 C18 C19 -177.0(3) . . . . ?
C17 C18 C19 C14 -1.9(5) . . . . ?
C15 C14 C19 C18 0.6(5) . . . . ?
C13 C14 C19 C18 -179.4(3) . . . . ?
C18 C17 C20 O3 173.9(4) . . . . ?
C16 C17 C20 O3 -4.7(5) . . . . ?
C18 C17 C20 O4 -5.6(5) . . . . ?
C16 C17 C20 O4 175.8(3) . . . . ?
O5 C21 C22 C24 -166.5(3) . . . . ?
O6 C21 C22 C24 14.1(4) . . . . ?
O5 C21 C22 C23 12.0(4) . . . . ?
O6 C21 C22 C23 -167.4(3) . . . . ?
C24 C22 C23 C24 -0.2(5) . . . 2_666 ?
C21 C22 C23 C24 -178.7(3) . . . 2_666 ?
C23 C22 C24 C23 0.2(5) . . . 2_666 ?
C21 C22 C24 C23 178.6(3) . . . 2_666 ?
C2 C1 N1 C5 -0.2(6) . . . . ?
C2 C1 N1 Zn1 166.6(3) . . . . ?
C4 C5 N1 C1 0.7(5) . . . . ?
C4 C5 N1 Zn1 -165.7(3) . . . . ?
N3 C8 N2 C7 -0.6(4) . . . . ?
C9 C8 N2 C7 179.6(4) . . . . ?
N3 C8 N2 Zn2 165.8(2) . . . 1_544 ?
C9 C8 N2 Zn2 -14.1(6) . . . 1_544 ?
C6 C7 N2 C8 0.0(4) . . . . ?
C6 C7 N2 Zn2 -167.8(2) . . . 1_544 ?
C11 C12 N3 C8 -3.0(5) . . . . ?
C11 C12 N3 C6 -179.0(4) . . . . ?
N2 C8 N3 C12 -176.0(3) . . . . ?
C9 C8 N3 C12 3.9(5) . . . . ?
N2 C8 N3 C6 0.9(4) . . . . ?
C9 C8 N3 C6 -179.2(3) . . . . ?
C7 C6 N3 C12 175.5(4) . . . . ?
C4 C6 N3 C12 -1.1(6) . . . . ?
C7 C6 N3 C8 -0.8(4) . . . . ?
C4 C6 N3 C8 -177.4(3) . . . . ?
O2 C13 O1 Zn1 -3.8(3) . . . . ?
C14 C13 O1 Zn1 175.1(3) . . . . ?
O1 C13 O2 Zn1 3.7(3) . . . . ?
C14 C13 O2 Zn1 -175.1(3) . . . . ?
O3 C20 O4 Zn2 -0.1(5) . . . 1_454 ?
C17 C20 O4 Zn2 179.5(2) . . . 1_454 ?
O6 C21 O5 Zn1 -14.7(5) . . . . ?
C22 C21 O5 Zn1 166.0(2) . . . . ?
O5 C21 O6 Zn2 -10.4(5) . . . . ?
C22 C21 O6 Zn2 169.0(2) . . . . ?
C1 N1 Zn1 O7 31.9(3) . . . 2_776 ?
C5 N1 Zn1 O7 -161.7(3) . . . 2_776 ?
C1 N1 Zn1 O5 -61.2(3) . . . . ?
C1 N1 Zn1 O1 -157.7(3) . . . . ?
C5 N1 Zn1 O1 8.7(3) . . . . ?
C1 N1 Zn1 O7 113.7(3) . . . . ?
C5 N1 Zn1 O7 -79.9(3) . . . . ?
C1 N1 Zn1 O2 -145.8(3) . . . . ?
C5 N1 Zn1 O2 20.5(4) . . . . ?
C1 N1 Zn1 C13 -155.1(3) . . . . ?
C5 N1 Zn1 C13 11.3(3) . . . . ?
C21 O5 Zn1 O7 29.4(3) . . . 2_776 ?
C21 O5 Zn1 N1 131.6(3) . . . . ?
C21 O5 Zn1 O1 -136.8(3) . . . . ?
C21 O5 Zn1 O7 -25.0(6) . . . . ?
C21 O5 Zn1 O2 -76.6(3) . . . . ?
C21 O5 Zn1 C13 -106.4(3) . . . . ?
C13 O1 Zn1 O7 -37.9(4) . . . 2_776 ?
C13 O1 Zn1 N1 175.7(2) . . . . ?
C13 O1 Zn1 O5 88.0(2) . . . . ?
C13 O1 Zn1 O7 -80.6(2) . . . . ?
C13 O1 Zn1 O2 2.13(19) . . . . ?
Zn2 O7 Zn1 O7 144.80(18) 2_776 . . 2_776 ?
Zn1 O7 Zn1 O7 0.0 2_776 . . 2_776 ?
Zn2 O7 Zn1 N1 44.57(16) 2_776 . . . ?
Zn1 O7 Zn1 N1 -100.23(10) 2_776 . . . ?
Zn2 O7 Zn1 O5 -159.6(4) 2_776 . . . ?
Zn1 O7 Zn1 O5 55.6(4) 2_776 . . . ?
Zn2 O7 Zn1 O1 -46.92(14) 2_776 . . . ?
Zn1 O7 Zn1 O1 168.29(10) 2_776 . . . ?
Zn2 O7 Zn1 O2 -107.38(15) 2_776 . . . ?
Zn1 O7 Zn1 O2 107.82(10) 2_776 . . . ?
Zn2 O7 Zn1 C13 -77.01(15) 2_776 . . . ?
Zn1 O7 Zn1 C13 138.19(11) 2_776 . . . ?
C13 O2 Zn1 O7 166.5(2) . . . 2_776 ?
C13 O2 Zn1 N1 -15.8(3) . . . . ?
C13 O2 Zn1 O5 -99.9(2) . . . . ?
C13 O2 Zn1 O1 -2.15(19) . . . . ?
C13 O2 Zn1 O7 89.9(2) . . . . ?
O2 C13 Zn1 O7 -18.5(3) . . . 2_776 ?
O1 C13 Zn1 O7 165.16(18) . . . 2_776 ?
O2 C13 Zn1 N1 171.24(19) . . . . ?
O1 C13 Zn1 N1 -5.1(2) . . . . ?
O2 C13 Zn1 O5 81.2(2) . . . . ?
O1 C13 Zn1 O5 -95.1(2) . . . . ?
O2 C13 Zn1 O1 176.3(3) . . . . ?
O2 C13 Zn1 O7 -86.4(2) . . . . ?
O1 C13 Zn1 O7 97.3(2) . . . . ?
O1 C13 Zn1 O2 -176.3(3) . . . . ?
C21 O6 Zn2 O7 10.1(3) . . . 2_776 ?
C21 O6 Zn2 O4 -118.8(3) . . . 1_656 ?
C21 O6 Zn2 N2 134.2(3) . . . 1_566 ?

_diffrn_measured_fraction_theta_max 0.998
_diffrn_reflns_theta_full        27.00
_diffrn_measured_fraction_theta_full 0.998
_refine_diff_density_max         1.092
_refine_diff_density_min         -1.448
_refine_diff_density_rms         0.142
_diffrn_standards_number         0
_diffrn_standards_interval_count 0
_diffrn_standards_interval_time  0
_diffrn_standards_decay_%        0

_exptl_crystal_preparation       Luminescent
_database_code_depnum_ccdc_archive 'CCDC 998459'
#######################################################################
#
#                 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_sdl24201

_audit_creation_method           SHELXL-97
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_formula_moiety         'C22 H15 N3 O9 Zn2'
_chemical_formula_sum            'C22 H15 N3 O9 Zn2'
_chemical_melting_point          ?

_exptl_crystal_description       block
_exptl_crystal_colour            orange-yellow

_diffrn_ambient_temperature      150(2)
_chemical_formula_weight         596.11

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   'P 21/c'
_symmetry_space_group_name_Hall  '-P 2ybc'
_symmetry_int_tables_number      14
_chemical_absolute_configuration ?

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                   7.5106(2)
_cell_length_b                   31.1959(7)
_cell_length_c                   10.5537(3)
_cell_angle_alpha                90.00
_cell_angle_beta                 118.658(2)
_cell_angle_gamma                90.00
_cell_volume                     2169.82(10)
_cell_formula_units_Z            4
_cell_measurement_temperature    150(2)
_cell_measurement_reflns_used    2934
_cell_measurement_theta_min      2.6
_cell_measurement_theta_max      27.4
_exptl_crystal_size_max          0.22
_exptl_crystal_size_mid          0.19
_exptl_crystal_size_min          0.16
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.825
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1200
_exptl_absorpt_coefficient_mu    2.274
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.6287
_exptl_absorpt_correction_T_max  0.7152
_exptl_absorpt_process_details   'SADABS (Sheldrick, 2003)'

_exptl_special_details           
; 
 ? 
;
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Bruker SMART APEXII'
_diffrn_measurement_method       ω
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            15465
_diffrn_reflns_av_R_equivalents  0.0778
_diffrn_reflns_av_unetI/netI     0.0886
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_k_min       -35
_diffrn_reflns_limit_k_max       39
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_theta_min         2.61
_diffrn_reflns_theta_max         26.50
_reflns_number_total             4476
_reflns_number_gt                3651
_reflns_threshold_expression     I>2σ

_computing_data_collection       'APEX2 (Bruker, 2007)'
_computing_cell_refinement       'SAINT (Bruker, 2007)'
_computing_data_reduction        'SAINT (Bruker, 2007)'
_computing_structure_solution    'SHELXTL (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXTL (Sheldrick, 2008)'
_computing_molecular_graphics    'SHELXTL (Sheldrick, 2008)'
_computing_publication_material  'DIAMOND (Brandenburg, 2006)'

_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)+(0.1135P)²+1.7955P] 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         4476
_refine_ls_number_parameters     325
_refine_ls_number_restraints     2
_refine_ls_R_factor_all          0.0867
_refine_ls_R_factor_gt           0.0774
_refine_ls_wR_factor_ref         0.2229
_refine_ls_wR_factor_gt          0.2130
_refine_ls_goodness_of_fit_ref   1.198
_refine_ls_restrained_S_all      1.213
_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
C1 C 0.9536(9) 1.08703(17) 0.5248(6) 0.0352(12) Uani 1 1 d . . .
C2 C 0.8484(9) 1.04976(16) 0.4997(6) 0.0344(11) Uani 1 1 d . . .
H2 H 0.7312 1.0430 0.4112 0.041 Uiso 1 1 calc R . .
C3 C 1.0932(8) 1.04461(17) 0.7193(6) 0.0336(11) Uani 1 1 d . . .
C4 C 1.2342(9) 1.0331(2) 0.8622(6) 0.0383(12) Uani 1 1 d . . .
H4 H 1.2270 1.0059 0.8998 0.046 Uiso 1 1 calc R . .
C5 C 1.3797(9) 1.06157(19) 0.9444(7) 0.0414(13) Uani 1 1 d . . .
H5 H 1.4768 1.0541 1.0403 0.050 Uiso 1 1 calc R . .
C6 C 1.3890(9) 1.10178(19) 0.8901(7) 0.0411(13) Uani 1 1 d . . .
H6 H 1.4908 1.1215 0.9506 0.049 Uiso 1 1 calc R . .
C7 C 1.2565(9) 1.11323(18) 0.7536(7) 0.0391(12) Uani 1 1 d . . .
H7 H 1.2633 1.1408 0.7180 0.047 Uiso 1 1 calc R . .
C8 C 0.3274(8) 0.92205(16) 0.2695(5) 0.0307(10) Uani 1 1 d . . .
C9 C 0.1958(8) 0.93404(16) 0.1275(5) 0.0306(10) Uani 1 1 d . . .
H9 H 0.2052 0.9620 0.0955 0.037 Uiso 1 1 calc R . .
C10 C 0.0506(8) 0.90556(16) 0.0320(5) 0.0305(10) Uani 1 1 d . . .
C11 C 0.0367(8) 0.86496(16) 0.0806(6) 0.0332(11) Uani 1 1 d . . .
H11 H -0.0641 0.8456 0.0170 0.040 Uiso 1 1 calc R . .
C12 C 0.1696(8) 0.85237(16) 0.2223(6) 0.0328(11) Uani 1 1 d . . .
C13 C 0.3174(8) 0.88064(16) 0.3157(6) 0.0317(11) Uani 1 1 d . . .
H13 H 0.4113 0.8718 0.4108 0.038 Uiso 1 1 calc R . .
C14 C 0.4788(8) 0.95327(16) 0.3710(6) 0.0327(11) Uani 1 1 d . . .
C15 C 0.1538(9) 0.80854(17) 0.2749(6) 0.0369(12) Uani 1 1 d . . .
C16 C 1.0341(10) 1.17914(19) 0.3298(7) 0.0440(14) Uani 1 1 d . . .
H16 H 1.1434 1.1951 0.3323 0.053 Uiso 1 1 calc R . .
C17 C 1.0772(10) 1.14618(19) 0.4251(7) 0.0433(13) Uani 1 1 d . . .
H17 H 1.2142 1.1389 0.4897 0.052 Uiso 1 1 calc R . .
C18 C 0.9191(9) 1.12316(16) 0.4272(6) 0.0355(12) Uani 1 1 d . . .
C19 C 0.7194(9) 1.13426(18) 0.3261(6) 0.0398(12) Uani 1 1 d . . .
H19 H 0.6073 1.1192 0.3228 0.048 Uiso 1 1 calc R . .
C20 C 0.6898(9) 1.16755(19) 0.2317(7) 0.0424(13) Uani 1 1 d . . .
H20 H 0.5545 1.1749 0.1632 0.051 Uiso 1 1 calc R . .
C21 C -0.0939(9) 0.91875(17) -0.1203(6) 0.0352(12) Uani 1 1 d . . .
C22 C 0.5427(11) 0.7276(2) 0.6884(8) 0.0490(15) Uani 1 1 d . . .
H22 H 0.5561 0.7576 0.6808 0.059 Uiso 1 1 calc R . .
N1 N 0.9305(7) 1.02327(13) 0.6159(5) 0.0341(10) Uani 1 1 d . . .
N2 N 1.1103(7) 1.08398(14) 0.6662(5) 0.0355(10) Uani 1 1 d . . .
N3 N 0.8418(8) 1.19006(14) 0.2316(5) 0.0411(11) Uani 1 1 d . . .
O1 O 0.6293(6) 0.93786(11) 0.4819(4) 0.0352(8) Uani 1 1 d . . .
O2 O 0.4491(5) 0.99294(11) 0.3447(4) 0.0333(8) Uani 1 1 d . . .
O3 O -0.0356(6) 0.95180(12) -0.1636(4) 0.0386(9) Uani 1 1 d . . .
O4 O -0.2511(6) 0.89870(14) -0.1934(5) 0.0479(10) Uani 1 1 d . . .
O5 O 0.2830(7) 0.79757(13) 0.4024(5) 0.0457(10) Uani 1 1 d . . .
O6 O 0.0139(7) 0.78353(12) 0.1943(4) 0.0429(10) Uani 1 1 d . . .
O7 O -0.0306(5) 0.73435(12) 0.4386(4) 0.0521(11) Uani 1 1 d D . .
H7B H -0.0323 0.7289 0.5141 0.063 Uiso 1 1 d D . .
H7A H -0.1223 0.7506 0.4046 0.063 Uiso 1 1 d D . .
O8 O 0.4009(7) 0.70919(14) 0.5810(5) 0.0525(11) Uani 1 1 d . . .
O9 O 0.6649(7) 0.71054(14) 0.8014(5) 0.0496(11) Uani 1 1 d . . .
Zn1 Zn 0.78098(9) 0.974945(18) 0.65010(6) 0.0321(2) Uani 1 1 d . . .
Zn2 Zn 0.19596(12) 0.73785(2) 0.40921(8) 0.0424(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
C1 C2 1.358(8) . ?
C1 N2 1.391(7) . ?
C1 C18 1.464(7) . ?
C2 N1 1.357(7) . ?
C2 H2 0.9500 . ?
C3 N1 1.360(7) . ?
C3 N2 1.381(7) . ?
C3 C4 1.411(8) . ?
C4 C5 1.350(8) . ?
C4 H4 0.9500 . ?
C5 C6 1.395(9) . ?
C5 H5 0.9500 . ?
C6 C7 1.349(8) . ?
C6 H6 0.9500 . ?
C7 N2 1.385(7) . ?
C7 H7 0.9500 . ?
C8 C9 1.393(7) . ?
C8 C13 1.396(7) . ?
C8 C14 1.491(7) . ?
C9 C10 1.393(7) . ?
C9 H9 0.9500 . ?
C10 C11 1.389(7) . ?
C10 C21 1.503(7) . ?
C11 C12 1.398(7) . ?
C11 H11 0.9500 . ?
C12 C13 1.390(8) . ?
C12 C15 1.502(7) . ?
C13 H13 0.9500 . ?
C14 O2 1.264(6) . ?
C14 O1 1.268(7) . ?
C15 O6 1.257(7) . ?
C15 O5 1.271(7) . ?
C15 Zn2 2.557(5) . ?
C16 N3 1.356(8) . ?
C16 C17 1.364(8) . ?
C16 H16 0.9500 . ?
C17 C18 1.397(8) . ?
C17 H17 0.9500 . ?
C18 C19 1.405(8) . ?
C19 C20 1.382(8) . ?
C19 H19 0.9500 . ?
C20 N3 1.341(8) . ?
C20 H20 0.9500 . ?
C21 O4 1.228(7) . ?
C21 O3 1.286(7) . ?
C22 O9 1.224(8) . ?
C22 O8 1.261(8) . ?
C22 H22 0.9500 . ?
N1 Zn1 2.013(4) . ?
N3 Zn2 2.027(5) 2_655 ?
O1 Zn1 1.961(4) . ?
O2 Zn1 2.021(4) 3_676 ?
O3 Zn1 1.920(4) 1_454 ?
O5 Zn2 1.987(4) . ?
O6 Zn2 2.463(4) . ?
O7 Zn2 1.874(4) . ?
O7 H7B 0.8200 . ?
O7 H7A 0.7889 . ?
O8 Zn2 1.944(5) . ?
Zn1 O3 1.920(4) 1_656 ?
Zn1 O2 2.021(4) 3_676 ?
Zn2 N3 2.027(5) 2_645 ?

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
C2 C1 N2 105.3(5) . . ?
C2 C1 C18 129.2(5) . . ?
N2 C1 C18 125.5(5) . . ?
N1 C2 C1 112.1(5) . . ?
N1 C2 H2 124.0 . . ?
C1 C2 H2 124.0 . . ?
N1 C3 N2 109.4(5) . . ?
N1 C3 C4 131.2(5) . . ?
N2 C3 C4 119.4(5) . . ?
C5 C4 C3 118.8(6) . . ?
C5 C4 H4 120.6 . . ?
C3 C4 H4 120.6 . . ?
C4 C5 C6 120.7(6) . . ?
C4 C5 H5 119.6 . . ?
C6 C5 H5 119.6 . . ?
C7 C6 C5 121.3(6) . . ?
C7 C6 H6 119.3 . . ?
C5 C6 H6 119.3 . . ?
C6 C7 N2 118.7(5) . . ?
C6 C7 H7 120.6 . . ?
N2 C7 H7 120.6 . . ?
C9 C8 C13 119.7(5) . . ?
C9 C8 C14 120.1(5) . . ?
C13 C8 C14 120.3(5) . . ?
C10 C9 C8 120.8(5) . . ?
C10 C9 H9 119.6 . . ?
C8 C9 H9 119.6 . . ?
C11 C10 C9 119.1(5) . . ?
C11 C10 C21 120.1(5) . . ?
C9 C10 C21 120.8(5) . . ?
C10 C11 C12 120.6(5) . . ?
C10 C11 H11 119.7 . . ?
C12 C11 H11 119.7 . . ?
C13 C12 C11 119.9(5) . . ?
C13 C12 C15 119.5(5) . . ?
C11 C12 C15 120.6(5) . . ?
C12 C13 C8 119.8(5) . . ?
C12 C13 H13 120.1 . . ?
C8 C13 H13 120.1 . . ?
O2 C14 O1 124.0(5) . . ?
O2 C14 C8 119.2(5) . . ?
O1 C14 C8 116.8(5) . . ?
O6 C15 O5 121.0(5) . . ?
O6 C15 C12 120.2(5) . . ?
O5 C15 C12 118.7(5) . . ?
O6 C15 Zn2 71.4(3) . . ?
O5 C15 Zn2 49.7(3) . . ?
C12 C15 Zn2 168.3(4) . . ?
N3 C16 C17 122.8(6) . . ?
N3 C16 H16 118.6 . . ?
C17 C16 H16 118.6 . . ?
C16 C17 C18 119.8(6) . . ?
C16 C17 H17 120.1 . . ?
C18 C17 H17 120.1 . . ?
C17 C18 C19 117.9(5) . . ?
C17 C18 C1 122.8(5) . . ?
C19 C18 C1 119.2(5) . . ?
C20 C19 C18 118.5(5) . . ?
C20 C19 H19 120.8 . . ?
C18 C19 H19 120.8 . . ?
N3 C20 C19 123.5(6) . . ?
N3 C20 H20 118.3 . . ?
C19 C20 H20 118.3 . . ?
O4 C21 O3 125.0(5) . . ?
O4 C21 C10 121.1(5) . . ?
O3 C21 C10 113.9(5) . . ?
O9 C22 O8 126.4(6) . . ?
O9 C22 H22 116.8 . . ?
O8 C22 H22 116.8 . . ?
C2 N1 C3 105.7(4) . . ?
C2 N1 Zn1 124.6(4) . . ?
C3 N1 Zn1 125.9(4) . . ?
C3 N2 C7 120.9(5) . . ?
C3 N2 C1 107.5(5) . . ?
C7 N2 C1 131.4(5) . . ?
C20 N3 C16 117.6(5) . . ?
C20 N3 Zn2 124.5(4) . 2_655 ?
C16 N3 Zn2 117.9(4) . 2_655 ?
C14 O1 Zn1 119.0(3) . . ?
C14 O2 Zn1 122.8(3) . 3_676 ?
C21 O3 Zn1 117.7(4) . 1_454 ?
C15 O5 Zn2 101.1(4) . . ?
C15 O6 Zn2 79.7(3) . . ?
Zn2 O7 H7B 127.7 . . ?
Zn2 O7 H7A 123.4 . . ?
H7B O7 H7A 99.1 . . ?
C22 O8 Zn2 125.4(4) . . ?
O3 Zn1 O1 121.67(16) 1_656 . ?
O3 Zn1 N1 106.09(19) 1_656 . ?
O1 Zn1 N1 114.28(17) . . ?
O3 Zn1 O2 111.20(16) 1_656 3_676 ?
O1 Zn1 O2 100.58(15) . 3_676 ?
N1 Zn1 O2 101.05(17) . 3_676 ?
O7 Zn2 O8 101.20(17) . . ?
O7 Zn2 O5 113.68(18) . . ?
O8 Zn2 O5 109.75(18) . . ?
O7 Zn2 N3 105.1(2) . 2_645 ?
O8 Zn2 N3 96.6(2) . 2_645 ?
O5 Zn2 N3 126.57(19) . 2_645 ?
O7 Zn2 O6 92.23(13) . . ?
O8 Zn2 O6 165.09(18) . . ?
O5 Zn2 O6 58.08(16) . . ?
N3 Zn2 O6 85.98(17) 2_645 . ?
O7 Zn2 C15 105.14(15) . . ?
O8 Zn2 C15 138.22(19) . . ?
O5 Zn2 C15 29.19(18) . . ?
N3 Zn2 C15 106.94(18) 2_645 . ?
O6 Zn2 C15 28.91(16) . . ?

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
N2 C1 C2 N1 -0.7(6) . . . . ?
C18 C1 C2 N1 177.9(5) . . . . ?
N1 C3 C4 C5 -177.7(5) . . . . ?
N2 C3 C4 C5 1.6(8) . . . . ?
C3 C4 C5 C6 0.9(8) . . . . ?
C4 C5 C6 C7 -1.4(9) . . . . ?
C5 C6 C7 N2 -0.7(8) . . . . ?
C13 C8 C9 C10 1.6(7) . . . . ?
C14 C8 C9 C10 -178.7(5) . . . . ?
C8 C9 C10 C11 0.8(7) . . . . ?
C8 C9 C10 C21 178.9(5) . . . . ?
C9 C10 C11 C12 -1.6(7) . . . . ?
C21 C10 C11 C12 -179.7(5) . . . . ?
C10 C11 C12 C13 0.0(8) . . . . ?
C10 C11 C12 C15 179.7(5) . . . . ?
C11 C12 C13 C8 2.5(8) . . . . ?
C15 C12 C13 C8 -177.3(5) . . . . ?
C9 C8 C13 C12 -3.3(7) . . . . ?
C14 C8 C13 C12 177.0(5) . . . . ?
C9 C8 C14 O2 21.4(7) . . . . ?
C13 C8 C14 O2 -158.9(5) . . . . ?
C9 C8 C14 O1 -160.2(5) . . . . ?
C13 C8 C14 O1 19.5(7) . . . . ?
C13 C12 C15 O6 176.0(5) . . . . ?
C11 C12 C15 O6 -3.8(8) . . . . ?
C13 C12 C15 O5 -3.4(8) . . . . ?
C11 C12 C15 O5 176.9(5) . . . . ?
C13 C12 C15 Zn2 -11(2) . . . . ?
C11 C12 C15 Zn2 169.6(16) . . . . ?
N3 C16 C17 C18 -2.3(9) . . . . ?
C16 C17 C18 C19 2.1(8) . . . . ?
C16 C17 C18 C1 179.1(5) . . . . ?
C2 C1 C18 C17 -142.0(6) . . . . ?
N2 C1 C18 C17 36.4(8) . . . . ?
C2 C1 C18 C19 35.0(8) . . . . ?
N2 C1 C18 C19 -146.7(5) . . . . ?
C17 C18 C19 C20 -0.8(8) . . . . ?
C1 C18 C19 C20 -177.9(5) . . . . ?
C18 C19 C20 N3 -0.3(9) . . . . ?
C11 C10 C21 O4 16.3(8) . . . . ?
C9 C10 C21 O4 -161.7(5) . . . . ?
C11 C10 C21 O3 -163.2(5) . . . . ?
C9 C10 C21 O3 18.7(7) . . . . ?
C1 C2 N1 C3 0.5(6) . . . . ?
C1 C2 N1 Zn1 159.5(4) . . . . ?
N2 C3 N1 C2 -0.1(6) . . . . ?
C4 C3 N1 C2 179.3(6) . . . . ?
N2 C3 N1 Zn1 -158.7(4) . . . . ?
C4 C3 N1 Zn1 20.6(8) . . . . ?
N1 C3 N2 C7 175.8(5) . . . . ?
C4 C3 N2 C7 -3.6(8) . . . . ?
N1 C3 N2 C1 -0.4(6) . . . . ?
C4 C3 N2 C1 -179.8(5) . . . . ?
C6 C7 N2 C3 3.2(8) . . . . ?
C6 C7 N2 C1 178.3(5) . . . . ?
C2 C1 N2 C3 0.6(6) . . . . ?
C18 C1 N2 C3 -178.1(5) . . . . ?
C2 C1 N2 C7 -175.0(5) . . . . ?
C18 C1 N2 C7 6.3(9) . . . . ?
C19 C20 N3 C16 0.2(9) . . . . ?
C19 C20 N3 Zn2 178.1(4) . . . 2_655 ?
C17 C16 N3 C20 1.2(9) . . . . ?
C17 C16 N3 Zn2 -176.9(5) . . . 2_655 ?
O2 C14 O1 Zn1 19.2(7) . . . . ?
C8 C14 O1 Zn1 -159.1(3) . . . . ?
O1 C14 O2 Zn1 -111.5(5) . . . 3_676 ?
C8 C14 O2 Zn1 66.8(5) . . . 3_676 ?
O4 C21 O3 Zn1 6.1(8) . . . 1_454 ?
C10 C21 O3 Zn1 -174.4(3) . . . 1_454 ?
O6 C15 O5 Zn2 2.6(6) . . . . ?
C12 C15 O5 Zn2 -178.1(4) . . . . ?
O5 C15 O6 Zn2 -2.1(5) . . . . ?
C12 C15 O6 Zn2 178.6(5) . . . . ?
O9 C22 O8 Zn2 174.8(5) . . . . ?
C14 O1 Zn1 O3 164.3(4) . . . 1_656 ?
C14 O1 Zn1 N1 -66.2(4) . . . . ?
C14 O1 Zn1 O2 41.2(4) . . . 3_676 ?
C2 N1 Zn1 O3 -175.6(4) . . . 1_656 ?
C3 N1 Zn1 O3 -20.7(5) . . . 1_656 ?
C2 N1 Zn1 O1 47.6(5) . . . . ?
C3 N1 Zn1 O1 -157.6(4) . . . . ?
C2 N1 Zn1 O2 -59.5(4) . . . 3_676 ?
C3 N1 Zn1 O2 95.3(4) . . . 3_676 ?
C22 O8 Zn2 O7 -105.1(6) . . . . ?
C22 O8 Zn2 O5 15.3(6) . . . . ?
C22 O8 Zn2 N3 148.1(6) . . . 2_645 ?
C22 O8 Zn2 O6 48.7(10) . . . . ?
C22 O8 Zn2 C15 23.3(7) . . . . ?
C15 O5 Zn2 O7 -78.4(4) . . . . ?
C15 O5 Zn2 O8 169.1(4) . . . . ?
C15 O5 Zn2 N3 54.3(4) . . . 2_645 ?
C15 O5 Zn2 O6 -1.3(3) . . . . ?
C15 O6 Zn2 O7 118.0(3) . . . . ?
C15 O6 Zn2 O8 -36.3(8) . . . . ?
C15 O6 Zn2 O5 1.3(3) . . . . ?
C15 O6 Zn2 N3 -137.0(3) . . . 2_645 ?
O6 C15 Zn2 O7 -66.0(3) . . . . ?
O5 C15 Zn2 O7 111.6(4) . . . . ?
C12 C15 Zn2 O7 120.0(19) . . . . ?
O6 C15 Zn2 O8 166.8(3) . . . . ?
O5 C15 Zn2 O8 -15.6(5) . . . . ?
C12 C15 Zn2 O8 -7(2) . . . . ?
O6 C15 Zn2 O5 -177.7(6) . . . . ?
C12 C15 Zn2 O5 8.4(17) . . . . ?
O6 C15 Zn2 N3 45.3(4) . . . 2_645 ?
O5 C15 Zn2 N3 -137.0(4) . . . 2_645 ?
C12 C15 Zn2 N3 -128.6(18) . . . 2_645 ?
O5 C15 Zn2 O6 177.7(6) . . . . ?
C12 C15 Zn2 O6 -174(2) . . . . ?

_diffrn_measured_fraction_theta_max 0.994
_diffrn_reflns_theta_full        26.50
_diffrn_measured_fraction_theta_full 0.994
_refine_diff_density_max         2.930
_refine_diff_density_min         -1.681
_refine_diff_density_rms         0.157
_diffrn_standards_number         0
_diffrn_standards_interval_count 0
_diffrn_standards_interval_time  0
_diffrn_standards_decay_%        0

_exptl_crystal_preparation       Luminescent
_database_code_depnum_ccdc_archive 'CCDC 998461'
#######################################################################
#
#                 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_sdl25701

_audit_creation_method           SHELXL-97
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_formula_moiety         'C21 H15 N3 O7 Zn, H2 O'
_chemical_formula_sum            'C21 H17 N3 O8 Zn'
_chemical_melting_point          ?

_exptl_crystal_description       block
_exptl_crystal_colour            orange-yellow

_diffrn_ambient_temperature      150(2)
_chemical_formula_weight         504.75

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'
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'
_symmetry_int_tables_number      2
_chemical_absolute_configuration ?

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

_cell_length_a                   7.2889(4)
_cell_length_b                   9.7098(5)
_cell_length_c                   13.6547(7)
_cell_angle_alpha                95.5580(10)
_cell_angle_beta                 90.9790(10)
_cell_angle_gamma                93.6880(10)
_cell_volume                     959.59(9)
_cell_formula_units_Z            2
_cell_measurement_temperature    150(2)
_cell_measurement_reflns_used    2547
_cell_measurement_theta_min      2.5
_cell_measurement_theta_max      26.4
_exptl_crystal_size_max          0.25
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.20
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.747
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             516
_exptl_absorpt_coefficient_mu    1.340
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.7305
_exptl_absorpt_correction_T_max  0.7754
_exptl_absorpt_process_details   'SADABS (Sheldrick, 2003)'

_exptl_special_details           
; 
 ? 
;
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Bruker SMART APEXII'
_diffrn_measurement_method       ω
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            9880
_diffrn_reflns_av_R_equivalents  0.0985
_diffrn_reflns_av_unetI/netI     0.1061
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_theta_min         1.50
_diffrn_reflns_theta_max         26.50
_reflns_number_total             3851
_reflns_number_gt                2902
_reflns_threshold_expression     I>2σ

_computing_data_collection       'APEX2 (Bruker, 2007)'
_computing_cell_refinement       'SAINT (Bruker, 2007)'
_computing_data_reduction        'SAINT (Bruker, 2007)'
_computing_structure_solution    'SHELXTL (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXTL (Sheldrick, 2008)'
_computing_molecular_graphics    'SHELXTL (Sheldrick, 2008)'
_computing_publication_material  'DIAMOND (Brandenburg, 2006)'

_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)+(0.1659P)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         3851
_refine_ls_number_parameters     298
_refine_ls_number_restraints     2
_refine_ls_R_factor_all          0.1166
_refine_ls_R_factor_gt           0.0788
_refine_ls_wR_factor_ref         0.2498
_refine_ls_wR_factor_gt          0.2030
_refine_ls_goodness_of_fit_ref   1.025
_refine_ls_restrained_S_all      1.038
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C 0.4084(7) 0.0024(6) 0.7436(4) 0.0323(11) Uani 1 1 d . . .
H1A H 0.4039 0.0951 0.7725 0.039 Uiso 1 1 calc R . .
C2 C 0.3382(7) -0.0445(6) 0.6525(4) 0.0308(11) Uani 1 1 d . . .
C3 C 0.4638(7) -0.2155(6) 0.7242(4) 0.0292(10) Uani 1 1 d . . .
C4 C 0.5112(7) -0.3514(6) 0.7336(4) 0.0338(11) Uani 1 1 d . . .
H4 H 0.5762 -0.3722 0.7907 0.041 Uiso 1 1 calc R . .
C5 C 0.4631(8) -0.4535(6) 0.6600(5) 0.0372(12) Uani 1 1 d . . .
H5A H 0.4953 -0.5459 0.6651 0.045 Uiso 1 1 calc R . .
C6 C 0.3651(8) -0.4204(6) 0.5762(4) 0.0373(13) Uani 1 1 d . . .
H6 H 0.3290 -0.4918 0.5258 0.045 Uiso 1 1 calc R . .
C7 C 0.3218(8) -0.2888(6) 0.5664(4) 0.0355(12) Uani 1 1 d . . .
H7 H 0.2568 -0.2679 0.5094 0.043 Uiso 1 1 calc R . .
C8 C 0.2649(7) 0.0355(6) 0.5776(4) 0.0317(11) Uani 1 1 d . . .
C9 C 0.2712(7) -0.0053(6) 0.4767(4) 0.0331(11) Uani 1 1 d . . .
H9 H 0.3219 -0.0899 0.4538 0.040 Uiso 1 1 calc R . .
C10 C 0.2032(8) 0.0785(6) 0.4112(4) 0.0355(12) Uani 1 1 d . . .
H10 H 0.2043 0.0481 0.3430 0.043 Uiso 1 1 calc R . .
C11 C 0.1304(8) 0.2429(6) 0.5354(4) 0.0361(12) Uani 1 1 d . . .
H11 H 0.0834 0.3300 0.5555 0.043 Uiso 1 1 calc R . .
C12 C 0.1918(8) 0.1629(6) 0.6068(4) 0.0345(12) Uani 1 1 d . . .
H12 H 0.1844 0.1941 0.6747 0.041 Uiso 1 1 calc R . .
C13 C 0.6644(7) 0.2212(5) 0.9555(4) 0.0303(11) Uani 1 1 d . . .
C14 C 0.7431(7) 0.3425(5) 1.0231(4) 0.0295(11) Uani 1 1 d . . .
C15 C 0.7301(7) 0.4777(5) 0.9973(4) 0.0294(11) Uani 1 1 d . . .
H15 H 0.6706 0.4926 0.9371 0.035 Uiso 1 1 calc R . .
C16 C 0.8042(7) 0.5905(5) 1.0594(4) 0.0289(10) Uani 1 1 d . . .
C17 C 0.8951(7) 0.5675(5) 1.1464(4) 0.0293(10) Uani 1 1 d . . .
H17 H 0.9473 0.6440 1.1886 0.035 Uiso 1 1 calc R . .
C18 C 0.9103(7) 0.4322(5) 1.1720(4) 0.0292(10) Uani 1 1 d . . .
C19 C 0.8326(7) 0.3212(5) 1.1100(4) 0.0284(10) Uani 1 1 d . . .
H19 H 0.8411 0.2294 1.1274 0.034 Uiso 1 1 calc R . .
C20 C 1.0011(7) 0.4075(6) 1.2672(4) 0.0305(11) Uani 1 1 d . . .
C21 C 0.7854(7) -0.2636(6) 1.0333(4) 0.0320(11) Uani 1 1 d . . .
N1 N 0.3727(6) -0.1857(5) 0.6399(3) 0.0292(9) Uani 1 1 d . . .
N2 N 0.4864(6) -0.1004(5) 0.7884(3) 0.0307(9) Uani 1 1 d . . .
N3 N 0.1354(6) 0.2011(5) 0.4387(4) 0.0338(10) Uani 1 1 d . . .
O1 O 0.8898(5) -0.0350(4) 0.8418(3) 0.0365(9) Uani 1 1 d . . .
O2 O 0.6427(5) 0.1050(4) 0.9947(3) 0.0326(8) Uani 1 1 d . . .
O3 O 0.6249(6) 0.2363(4) 0.8698(3) 0.0398(9) Uani 1 1 d . . .
O4 O 1.0537(6) 0.5039(4) 1.3295(3) 0.0376(9) Uani 1 1 d . . .
O5 O 1.0153(6) 0.2773(4) 1.2797(3) 0.0352(9) Uani 1 1 d . . .
H5 H 1.0672 0.2710 1.3344 0.053 Uiso 1 1 calc R . .
O6 O 0.8503(6) -0.1642(4) 1.0901(3) 0.0385(9) Uani 1 1 d . . .
O7 O 0.6959(5) -0.2535(4) 0.9532(3) 0.0341(8) Uani 1 1 d . . .
O8 O 0.2868(7) 0.7386(5) 0.3238(3) 0.0522(12) Uani 1 1 d D . .
H8B H 0.2207 0.6782 0.3530 0.063 Uiso 1 1 d RD . .
H8A H 0.3205 0.7781 0.2714 0.063 Uiso 1 1 d RD . .
Zn1 Zn 0.63864(8) -0.07261(6) 0.91446(4) 0.0309(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
C1 C2 1.363(8) . ?
C1 N2 1.368(7) . ?
C1 H1A 0.9500 . ?
C2 N1 1.405(7) . ?
C2 C8 1.457(8) . ?
C3 N2 1.351(7) . ?
C3 N1 1.383(7) . ?
C3 C4 1.402(8) . ?
C4 C5 1.367(8) . ?
C4 H4 0.9500 . ?
C5 C6 1.412(9) . ?
C5 H5A 0.9500 . ?
C6 C7 1.354(8) . ?
C6 H6 0.9500 . ?
C7 N1 1.376(7) . ?
C7 H7 0.9500 . ?
C8 C9 1.398(8) . ?
C8 C12 1.404(8) . ?
C9 C10 1.374(9) . ?
C9 H9 0.9500 . ?
C10 N3 1.340(7) . ?
C10 H10 0.9500 . ?
C11 N3 1.346(8) . ?
C11 C12 1.390(8) . ?
C11 H11 0.9500 . ?
C12 H12 0.9500 . ?
C13 O3 1.225(7) . ?
C13 O2 1.297(7) . ?
C13 C14 1.501(7) . ?
C14 C19 1.383(8) . ?
C14 C15 1.401(7) . ?
C15 C16 1.392(7) . ?
C15 H15 0.9500 . ?
C16 C17 1.394(8) . ?
C16 C21 1.507(7) 1_565 ?
C17 C18 1.403(8) . ?
C17 H17 0.9500 . ?
C18 C19 1.388(7) . ?
C18 C20 1.495(7) . ?
C19 H19 0.9500 . ?
C20 O4 1.238(7) . ?
C20 O5 1.303(7) . ?
C21 O6 1.241(7) . ?
C21 O7 1.280(7) . ?
C21 C16 1.507(7) 1_545 ?
N2 Zn1 2.019(5) . ?
O1 Zn1 2.125(4) . ?
O2 Zn1 1.950(4) . ?
O2 Zn1 2.433(4) 2_657 ?
O5 H5 0.8400 . ?
O7 Zn1 1.950(4) . ?
O8 H8B 0.8663 . ?
O8 H8A 0.8758 . ?
Zn1 O2 2.433(4) 2_657 ?

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
C2 C1 N2 111.7(5) . . ?
C2 C1 H1A 124.2 . . ?
N2 C1 H1A 124.2 . . ?
C1 C2 N1 105.2(5) . . ?
C1 C2 C8 128.3(5) . . ?
N1 C2 C8 126.0(5) . . ?
N2 C3 N1 109.9(5) . . ?
N2 C3 C4 130.2(5) . . ?
N1 C3 C4 119.8(5) . . ?
C5 C4 C3 119.4(5) . . ?
C5 C4 H4 120.3 . . ?
C3 C4 H4 120.3 . . ?
C4 C5 C6 119.4(5) . . ?
C4 C5 H5A 120.3 . . ?
C6 C5 H5A 120.3 . . ?
C7 C6 C5 121.2(5) . . ?
C7 C6 H6 119.4 . . ?
C5 C6 H6 119.4 . . ?
C6 C7 N1 119.3(5) . . ?
C6 C7 H7 120.3 . . ?
N1 C7 H7 120.3 . . ?
C9 C8 C12 117.8(5) . . ?
C9 C8 C2 123.1(5) . . ?
C12 C8 C2 119.0(5) . . ?
C10 C9 C8 119.2(5) . . ?
C10 C9 H9 120.4 . . ?
C8 C9 H9 120.4 . . ?
N3 C10 C9 123.3(6) . . ?
N3 C10 H10 118.4 . . ?
C9 C10 H10 118.4 . . ?
N3 C11 C12 122.1(5) . . ?
N3 C11 H11 118.9 . . ?
C12 C11 H11 118.9 . . ?
C11 C12 C8 119.3(5) . . ?
C11 C12 H12 120.4 . . ?
C8 C12 H12 120.4 . . ?
O3 C13 O2 124.6(5) . . ?
O3 C13 C14 120.0(5) . . ?
O2 C13 C14 115.4(5) . . ?
C19 C14 C15 119.7(5) . . ?
C19 C14 C13 120.2(5) . . ?
C15 C14 C13 120.1(5) . . ?
C16 C15 C14 120.3(5) . . ?
C16 C15 H15 119.9 . . ?
C14 C15 H15 119.9 . . ?
C15 C16 C17 119.4(5) . . ?
C15 C16 C21 120.4(5) . 1_565 ?
C17 C16 C21 120.2(5) . 1_565 ?
C16 C17 C18 120.5(5) . . ?
C16 C17 H17 119.7 . . ?
C18 C17 H17 119.7 . . ?
C19 C18 C17 119.2(5) . . ?
C19 C18 C20 120.2(5) . . ?
C17 C18 C20 120.6(5) . . ?
C14 C19 C18 120.9(5) . . ?
C14 C19 H19 119.6 . . ?
C18 C19 H19 119.6 . . ?
O4 C20 O5 123.4(5) . . ?
O4 C20 C18 122.1(5) . . ?
O5 C20 C18 114.5(5) . . ?
O6 C21 O7 125.0(5) . . ?
O6 C21 C16 119.6(5) . 1_545 ?
O7 C21 C16 115.4(5) . 1_545 ?
C7 N1 C3 120.8(5) . . ?
C7 N1 C2 131.8(5) . . ?
C3 N1 C2 107.2(4) . . ?
C3 N2 C1 106.0(5) . . ?
C3 N2 Zn1 128.0(4) . . ?
C1 N2 Zn1 125.3(4) . . ?
C10 N3 C11 118.4(5) . . ?
C13 O2 Zn1 121.2(3) . . ?
C13 O2 Zn1 115.7(3) . 2_657 ?
Zn1 O2 Zn1 100.29(15) . 2_657 ?
C20 O5 H5 109.5 . . ?
C21 O7 Zn1 120.8(4) . . ?
H8B O8 H8A 152.1 . . ?
O2 Zn1 O7 128.96(17) . . ?
O2 Zn1 N2 119.22(18) . . ?
O7 Zn1 N2 108.89(18) . . ?
O2 Zn1 O1 97.11(16) . . ?
O7 Zn1 O1 95.57(16) . . ?
N2 Zn1 O1 93.94(17) . . ?
O2 Zn1 O2 79.71(15) . 2_657 ?
O7 Zn1 O2 85.57(15) . 2_657 ?
N2 Zn1 O2 88.72(16) . 2_657 ?
O1 Zn1 O2 176.59(14) . 2_657 ?

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
N2 C1 C2 N1 0.6(6) . . . . ?
N2 C1 C2 C8 -171.9(5) . . . . ?
N2 C3 C4 C5 175.8(5) . . . . ?
N1 C3 C4 C5 -1.4(8) . . . . ?
C3 C4 C5 C6 -0.6(8) . . . . ?
C4 C5 C6 C7 1.6(8) . . . . ?
C5 C6 C7 N1 -0.6(8) . . . . ?
C1 C2 C8 C9 150.9(6) . . . . ?
N1 C2 C8 C9 -20.2(8) . . . . ?
C1 C2 C8 C12 -26.0(8) . . . . ?
N1 C2 C8 C12 162.9(5) . . . . ?
C12 C8 C9 C10 -1.3(8) . . . . ?
C2 C8 C9 C10 -178.2(5) . . . . ?
C8 C9 C10 N3 2.2(8) . . . . ?
N3 C11 C12 C8 1.3(8) . . . . ?
C9 C8 C12 C11 -0.4(8) . . . . ?
C2 C8 C12 C11 176.7(5) . . . . ?
O3 C13 C14 C19 -162.7(5) . . . . ?
O2 C13 C14 C19 17.6(7) . . . . ?
O3 C13 C14 C15 15.6(8) . . . . ?
O2 C13 C14 C15 -164.0(5) . . . . ?
C19 C14 C15 C16 -1.1(8) . . . . ?
C13 C14 C15 C16 -179.5(5) . . . . ?
C14 C15 C16 C17 1.6(7) . . . . ?
C14 C15 C16 C21 -178.1(5) . . . 1_565 ?
C15 C16 C17 C18 -0.8(8) . . . . ?
C21 C16 C17 C18 178.9(5) 1_565 . . . ?
C16 C17 C18 C19 -0.4(8) . . . . ?
C16 C17 C18 C20 -177.5(5) . . . . ?
C15 C14 C19 C18 -0.1(8) . . . . ?
C13 C14 C19 C18 178.3(5) . . . . ?
C17 C18 C19 C14 0.8(8) . . . . ?
C20 C18 C19 C14 177.9(5) . . . . ?
C19 C18 C20 O4 -171.8(5) . . . . ?
C17 C18 C20 O4 5.3(8) . . . . ?
C19 C18 C20 O5 6.5(7) . . . . ?
C17 C18 C20 O5 -176.4(5) . . . . ?
C6 C7 N1 C3 -1.4(7) . . . . ?
C6 C7 N1 C2 -175.8(5) . . . . ?
N2 C3 N1 C7 -175.3(4) . . . . ?
C4 C3 N1 C7 2.4(7) . . . . ?
N2 C3 N1 C2 0.4(5) . . . . ?
C4 C3 N1 C2 178.1(5) . . . . ?
C1 C2 N1 C7 174.4(5) . . . . ?
C8 C2 N1 C7 -12.9(9) . . . . ?
C1 C2 N1 C3 -0.6(5) . . . . ?
C8 C2 N1 C3 172.1(5) . . . . ?
N1 C3 N2 C1 0.0(5) . . . . ?
C4 C3 N2 C1 -177.4(5) . . . . ?
N1 C3 N2 Zn1 -170.7(3) . . . . ?
C4 C3 N2 Zn1 11.9(8) . . . . ?
C2 C1 N2 C3 -0.4(6) . . . . ?
C2 C1 N2 Zn1 170.6(4) . . . . ?
C9 C10 N3 C11 -1.3(8) . . . . ?
C12 C11 N3 C10 -0.5(8) . . . . ?
O3 C13 O2 Zn1 25.1(7) . . . . ?
C14 C13 O2 Zn1 -155.2(3) . . . . ?
O3 C13 O2 Zn1 -96.4(6) . . . 2_657 ?
C14 C13 O2 Zn1 83.2(5) . . . 2_657 ?
O6 C21 O7 Zn1 -3.6(7) . . . . ?
C16 C21 O7 Zn1 174.2(3) 1_545 . . . ?
C13 O2 Zn1 O7 155.7(4) . . . . ?
Zn1 O2 Zn1 O7 -75.6(2) 2_657 . . . ?
C13 O2 Zn1 N2 -46.0(4) . . . . ?
Zn1 O2 Zn1 N2 82.7(2) 2_657 . . . ?
C13 O2 Zn1 O1 52.6(4) . . . . ?
Zn1 O2 Zn1 O1 -178.75(15) 2_657 . . . ?
C13 O2 Zn1 O2 -128.7(5) . . . 2_657 ?
Zn1 O2 Zn1 O2 0.0 2_657 . . 2_657 ?
C21 O7 Zn1 O2 -17.1(5) . . . . ?
C21 O7 Zn1 N2 -177.2(4) . . . . ?
C21 O7 Zn1 O1 86.7(4) . . . . ?
C21 O7 Zn1 O2 -90.0(4) . . . 2_657 ?
C3 N2 Zn1 O2 -178.9(4) . . . . ?
C1 N2 Zn1 O2 12.1(5) . . . . ?
C3 N2 Zn1 O7 -16.5(5) . . . . ?
C1 N2 Zn1 O7 174.4(4) . . . . ?
C3 N2 Zn1 O1 80.7(4) . . . . ?
C1 N2 Zn1 O1 -88.3(4) . . . . ?
C3 N2 Zn1 O2 -101.4(4) . . . 2_657 ?
C1 N2 Zn1 O2 89.5(4) . . . 2_657 ?

_diffrn_measured_fraction_theta_max 0.967
_diffrn_reflns_theta_full        26.50
_diffrn_measured_fraction_theta_full 0.967
_refine_diff_density_max         0.933
_refine_diff_density_min         -1.917
_refine_diff_density_rms         0.275
_diffrn_standards_number         0
_diffrn_standards_interval_count 0
_diffrn_standards_interval_time  0
_diffrn_standards_decay_%        0

_database_code_depnum_ccdc_archive 'CCDC 998462'
#######################################################################
#
#                 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_sdl236

_audit_creation_method           SHELXL-97
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_formula_moiety         '2(C21 H13 N3 O7 Zn2), 2(H1 O0.50)'
_chemical_formula_sum            'C42 H28 N6 O15 Zn4'
_chemical_melting_point          ?

_exptl_crystal_description       block
_exptl_crystal_colour            orange-yellow

_diffrn_ambient_temperature      150(2)
_chemical_formula_weight         1118.18

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   'C 2/c'
_symmetry_space_group_name_Hall  'F 2 -2d'
_symmetry_int_tables_number      15
_chemical_absolute_configuration ?

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                   20.233(4)
_cell_length_b                   10.901(2)
_cell_length_c                   20.355(4)
_cell_angle_alpha                90.00
_cell_angle_beta                 115.467(10)
_cell_angle_gamma                90.00
_cell_volume                     4053.3(13)
_cell_formula_units_Z            4
_cell_measurement_temperature    150(2)
_cell_measurement_reflns_used    6718
_cell_measurement_theta_min      2.2
_cell_measurement_theta_max      27.9
_exptl_crystal_size_max          0.15
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.14
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.832
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             2248
_exptl_absorpt_coefficient_mu    2.422
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.7112
_exptl_absorpt_correction_T_max  0.7264
_exptl_absorpt_process_details   'SADABS (Sheldrick, 2003)'

_exptl_special_details           
; 
 ? 
;
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Bruker SMART APEXII'
_diffrn_measurement_method       ω
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            22682
_diffrn_reflns_av_R_equivalents  0.0839
_diffrn_reflns_av_unetI/netI     0.0607
_diffrn_reflns_limit_h_min       -25
_diffrn_reflns_limit_h_max       24
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_l_min       -25
_diffrn_reflns_limit_l_max       25
_diffrn_reflns_theta_min         2.18
_diffrn_reflns_theta_max         26.50
_reflns_number_total             4202
_reflns_number_gt                3309
_reflns_threshold_expression     I>2σ

_computing_data_collection       'APEX2 (Bruker, 2007)'
_computing_cell_refinement       'SAINT (Bruker, 2007)'
_computing_data_reduction        'SAINT (Bruker, 2007)'
_computing_structure_solution    'SHELXTL (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXTL (Sheldrick, 2008)'
_computing_molecular_graphics    'SHELXTL (Sheldrick, 2008)'
_computing_publication_material  'DIAMOND (Brandenburg, 2006)'

_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)+(0.1700P)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     SHELXL
_refine_ls_extinction_coef       0.0028(5)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_number_reflns         4202
_refine_ls_number_parameters     315
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0906
_refine_ls_R_factor_gt           0.0842
_refine_ls_wR_factor_ref         0.2432
_refine_ls_wR_factor_gt          0.2378
_refine_ls_goodness_of_fit_ref   1.069
_refine_ls_restrained_S_all      1.069
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C 0.0699(3) -0.1935(6) 0.4202(3) 0.0406(13) Uani 1 1 d . . .
H1 H 0.0303 -0.1459 0.4195 0.049 Uiso 1 1 calc R . .
C2 C 0.1023(3) -0.2880(5) 0.4675(3) 0.0411(13) Uani 1 1 d . . .
C3 C 0.1567(3) -0.2603(5) 0.3932(3) 0.0407(13) Uani 1 1 d . . .
C4 C 0.2073(4) -0.2839(6) 0.3635(4) 0.0471(15) Uani 1 1 d . . .
H4 H 0.2053 -0.2398 0.3224 0.057 Uiso 1 1 calc R . .
C5 C 0.2588(4) -0.3722(6) 0.3960(4) 0.0480(15) Uani 1 1 d . . .
H5 H 0.2923 -0.3925 0.3763 0.058 Uiso 1 1 calc R . .
C6 C 0.2630(3) -0.4340(6) 0.4587(4) 0.0460(15) Uani 1 1 d . . .
H6 H 0.3012 -0.4916 0.4823 0.055 Uiso 1 1 calc R . .
C7 C 0.2141(3) -0.4125(6) 0.4852(3) 0.0440(14) Uani 1 1 d . . .
H7 H 0.2174 -0.4543 0.5275 0.053 Uiso 1 1 calc R . .
C8 C -0.1013(3) 0.2252(6) 0.0634(3) 0.0405(13) Uani 1 1 d . . .
C9 C 0.0691(4) 0.4198(6) 0.1444(4) 0.0507(16) Uani 1 1 d . . .
H9 H 0.0633 0.4481 0.1858 0.061 Uiso 1 1 calc R . .
C10 C 0.0837(4) 0.5044(6) 0.1017(4) 0.0518(16) Uani 1 1 d . . .
H10 H 0.0876 0.5891 0.1135 0.062 Uiso 1 1 calc R . .
C11 C 0.0724(3) 0.2607(6) 0.0721(3) 0.0400(13) Uani 1 1 d . . .
H11 H 0.0676 0.1756 0.0610 0.048 Uiso 1 1 calc R . .
C12 C 0.0895(3) 0.3395(5) 0.0274(3) 0.0411(14) Uani 1 1 d . . .
C13 C 0.0927(4) 0.4647(6) 0.0422(4) 0.0457(15) Uani 1 1 d . . .
H13 H 0.1011 0.5219 0.0113 0.055 Uiso 1 1 calc R . .
C14 C 0.1145(3) -0.0717(5) 0.1752(3) 0.0379(13) Uani 1 1 d . . .
C15 C 0.1475(3) -0.1423(5) 0.1336(3) 0.0381(13) Uani 1 1 d . . .
C16 C 0.1129(3) -0.1441(5) 0.0577(3) 0.0383(13) Uani 1 1 d . . .
H16 H 0.0703 -0.0960 0.0324 0.046 Uiso 1 1 calc R . .
C17 C 0.1406(3) -0.2160(5) 0.0190(3) 0.0369(12) Uani 1 1 d . . .
C18 C 0.2049(3) -0.2814(5) 0.0565(3) 0.0393(13) Uani 1 1 d . . .
H18 H 0.2237 -0.3315 0.0303 0.047 Uiso 1 1 calc R . .
C19 C 0.2419(3) -0.2743(5) 0.1316(3) 0.0385(13) Uani 1 1 d . . .
C20 C 0.2129(3) -0.2061(5) 0.1702(3) 0.0401(13) Uani 1 1 d . . .
H20 H 0.2375 -0.2028 0.2218 0.048 Uiso 1 1 calc R . .
C21 C 0.1880(3) 0.1558(5) 0.3298(3) 0.0410(14) Uani 1 1 d . . .
N1 N 0.0626(3) 0.2987(5) 0.1295(3) 0.0421(12) Uani 1 1 d . . .
N2 N 0.1022(3) -0.1766(5) 0.3736(3) 0.0415(12) Uani 1 1 d . . .
N3 N 0.1587(3) -0.3292(4) 0.4505(3) 0.0378(11) Uani 1 1 d . . .
O1 O 0.0754(2) 0.0197(4) 0.1444(2) 0.0441(10) Uani 1 1 d . . .
O2 O 0.1260(2) -0.1102(4) 0.2378(2) 0.0457(10) Uani 1 1 d . . .
O3 O 0.1445(3) 0.1927(4) 0.2681(2) 0.0520(12) Uani 1 1 d . . .
O4 O 0.1784(2) 0.0638(4) 0.3628(2) 0.0439(10) Uani 1 1 d . . .
O5 O 0.0000 0.0484(5) 0.2500 0.0366(12) Uani 1 2 d S . .
O6 O -0.0593(2) 0.1372(4) 0.0955(2) 0.0422(10) Uani 1 1 d . . .
O7 O -0.1111(3) 0.3207(4) 0.0910(3) 0.0529(12) Uani 1 1 d . . .
O8 O 0.0000 0.2995(8) 0.2500 0.109(5) Uani 1 2 d SD . .
H8 H -0.0290 0.3489 0.2232 0.131 Uiso 1 1 d GD . .
O9 O 0.0722(7) 0.4896(11) 0.3064(6) 0.071(3) Uani 0.50 1 d P . .
Zn1 Zn 0.03473(3) 0.15871(6) 0.19022(4) 0.0370(3) Uani 1 1 d . . .
Zn2 Zn 0.08949(3) -0.03478(6) 0.30722(4) 0.0377(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
C1 C2 1.370(9) . ?
C1 N2 1.375(8) . ?
C1 H1 0.9500 . ?
C2 N3 1.400(8) . ?
C2 C12 1.462(9) 6_556 ?
C3 N2 1.352(8) . ?
C3 N3 1.373(8) . ?
C3 C4 1.419(9) . ?
C4 C5 1.363(9) . ?
C4 H4 0.9500 . ?
C5 C6 1.412(9) . ?
C5 H5 0.9500 . ?
C6 C7 1.337(9) . ?
C6 H6 0.9500 . ?
C7 N3 1.379(8) . ?
C7 H7 0.9500 . ?
C8 O7 1.239(7) . ?
C8 O6 1.262(7) . ?
C8 C17 1.520(8) 5 ?
C9 N1 1.348(8) . ?
C9 C10 1.384(10) . ?
C9 H9 0.9500 . ?
C10 C13 1.370(10) . ?
C10 H10 0.9500 . ?
C11 N1 1.333(8) . ?
C11 C12 1.398(9) . ?
C11 H11 0.9500 . ?
C12 C13 1.393(8) . ?
C12 C2 1.462(9) 6 ?
C13 H13 0.9500 . ?
C14 O1 1.259(7) . ?
C14 O2 1.265(7) . ?
C14 C15 1.497(9) . ?
C15 C20 1.394(8) . ?
C15 C16 1.395(8) . ?
C16 C17 1.388(8) . ?
C16 H16 0.9500 . ?
C17 C18 1.389(8) . ?
C17 C8 1.520(8) 5 ?
C18 C19 1.384(8) . ?
C18 H18 0.9500 . ?
C19 C20 1.384(8) . ?
C19 C21 1.500(8) 4_545 ?
C20 H20 0.9500 . ?
C21 O3 1.250(8) . ?
C21 O4 1.267(8) . ?
C21 C19 1.500(8) 4 ?
N1 Zn1 2.185(5) . ?
N2 Zn2 1.996(5) . ?
O1 Zn1 2.123(4) . ?
O2 Zn2 2.028(4) . ?
O3 Zn1 2.134(4) . ?
O4 Zn2 1.980(4) . ?
O5 Zn2 1.909(3) . ?
O5 Zn2 1.909(3) 2 ?
O5 Zn1 2.038(3) . ?
O5 Zn1 2.038(3) 2 ?
O6 Zn1 2.059(4) . ?
O8 Zn1 2.251(6) . ?
O8 Zn1 2.251(6) 2 ?
O8 H8 0.8100 . ?
Zn1 Zn2 3.0130(10) . ?

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
C2 C1 N2 111.1(5) . . ?
C2 C1 H1 124.4 . . ?
N2 C1 H1 124.4 . . ?
C1 C2 N3 105.1(5) . . ?
C1 C2 C12 132.2(6) . 6_556 ?
N3 C2 C12 122.6(5) . 6_556 ?
N2 C3 N3 110.0(6) . . ?
N2 C3 C4 130.0(6) . . ?
N3 C3 C4 120.0(6) . . ?
C5 C4 C3 117.5(6) . . ?
C5 C4 H4 121.2 . . ?
C3 C4 H4 121.2 . . ?
C4 C5 C6 120.8(6) . . ?
C4 C5 H5 119.6 . . ?
C6 C5 H5 119.6 . . ?
C7 C6 C5 121.0(6) . . ?
C7 C6 H6 119.5 . . ?
C5 C6 H6 119.5 . . ?
C6 C7 N3 119.3(6) . . ?
C6 C7 H7 120.4 . . ?
N3 C7 H7 120.4 . . ?
O7 C8 O6 127.5(6) . . ?
O7 C8 C17 116.5(5) . 5 ?
O6 C8 C17 115.9(5) . 5 ?
N1 C9 C10 122.4(7) . . ?
N1 C9 H9 118.8 . . ?
C10 C9 H9 118.8 . . ?
C13 C10 C9 119.4(6) . . ?
C13 C10 H10 120.3 . . ?
C9 C10 H10 120.3 . . ?
N1 C11 C12 123.4(6) . . ?
N1 C11 H11 118.3 . . ?
C12 C11 H11 118.3 . . ?
C13 C12 C11 117.6(6) . . ?
C13 C12 C2 123.2(6) . 6 ?
C11 C12 C2 119.2(5) . 6 ?
C10 C13 C12 119.3(6) . . ?
C10 C13 H13 120.4 . . ?
C12 C13 H13 120.4 . . ?
O1 C14 O2 124.6(6) . . ?
O1 C14 C15 117.5(5) . . ?
O2 C14 C15 117.8(5) . . ?
C20 C15 C16 119.6(6) . . ?
C20 C15 C14 120.3(5) . . ?
C16 C15 C14 120.1(5) . . ?
C17 C16 C15 120.3(5) . . ?
C17 C16 H16 119.9 . . ?
C15 C16 H16 119.9 . . ?
C16 C17 C18 119.3(6) . . ?
C16 C17 C8 121.1(5) . 5 ?
C18 C17 C8 119.6(5) . 5 ?
C19 C18 C17 120.8(6) . . ?
C19 C18 H18 119.6 . . ?
C17 C18 H18 119.6 . . ?
C20 C19 C18 119.8(5) . . ?
C20 C19 C21 120.8(5) . 4_545 ?
C18 C19 C21 119.4(5) . 4_545 ?
C19 C20 C15 120.1(6) . . ?
C19 C20 H20 120.0 . . ?
C15 C20 H20 120.0 . . ?
O3 C21 O4 125.8(6) . . ?
O3 C21 C19 117.5(6) . 4 ?
O4 C21 C19 116.8(5) . 4 ?
C11 N1 C9 117.8(6) . . ?
C11 N1 Zn1 116.8(4) . . ?
C9 N1 Zn1 125.4(5) . . ?
C3 N2 C1 105.9(5) . . ?
C3 N2 Zn2 125.0(4) . . ?
C1 N2 Zn2 127.5(4) . . ?
C3 N3 C7 121.1(6) . . ?
C3 N3 C2 107.8(5) . . ?
C7 N3 C2 130.8(6) . . ?
C14 O1 Zn1 128.7(4) . . ?
C14 O2 Zn2 127.1(4) . . ?
C21 O3 Zn1 138.5(4) . . ?
C21 O4 Zn2 115.8(4) . . ?
Zn2 O5 Zn2 123.3(3) . 2 ?
Zn2 O5 Zn1 99.46(4) . . ?
Zn2 O5 Zn1 113.33(4) 2 . ?
Zn2 O5 Zn1 113.33(4) . 2 ?
Zn2 O5 Zn1 99.46(4) 2 2 ?
Zn1 O5 Zn1 107.7(3) . 2 ?
C8 O6 Zn1 122.9(4) . . ?
Zn1 O8 Zn1 94.0(3) . 2 ?
Zn1 O8 H8 121(10) 2 . ?
O5 Zn1 O6 94.30(13) . . ?
O5 Zn1 O1 98.03(18) . . ?
O6 Zn1 O1 83.31(17) . . ?
O5 Zn1 O3 100.04(13) . . ?
O6 Zn1 O3 164.39(19) . . ?
O1 Zn1 O3 88.57(19) . . ?
O5 Zn1 N1 171.38(18) . . ?
O6 Zn1 N1 84.79(18) . . ?
O1 Zn1 N1 90.39(19) . . ?
O3 Zn1 N1 81.94(18) . . ?
O5 Zn1 O8 79.1(2) . . ?
O6 Zn1 O8 101.92(13) . . ?
O1 Zn1 O8 174.17(14) . . ?
O3 Zn1 O8 86.93(15) . . ?
N1 Zn1 O8 92.6(2) . . ?
O5 Zn1 Zn2 38.68(6) . . ?
O6 Zn1 Zn2 122.56(12) . . ?
O1 Zn1 Zn2 76.55(12) . . ?
O3 Zn1 Zn2 67.84(12) . . ?
N1 Zn1 Zn2 147.07(13) . . ?
O8 Zn1 Zn2 98.29(13) . . ?
O5 Zn2 O4 118.8(2) . . ?
O5 Zn2 N2 126.39(19) . . ?
O4 Zn2 N2 102.3(2) . . ?
O5 Zn2 O2 107.54(13) . . ?
O4 Zn2 O2 95.97(19) . . ?
N2 Zn2 O2 100.3(2) . . ?
O5 Zn2 Zn1 41.86(9) . . ?
O4 Zn2 Zn1 90.37(13) . . ?
N2 Zn2 Zn1 166.88(16) . . ?
O2 Zn2 Zn1 81.57(13) . . ?

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
N2 C1 C2 N3 1.6(7) . . . . ?
N2 C1 C2 C12 178.5(6) . . . 6_556 ?
N2 C3 C4 C5 177.8(7) . . . . ?
N3 C3 C4 C5 -3.0(9) . . . . ?
C3 C4 C5 C6 -2.5(10) . . . . ?
C4 C5 C6 C7 3.9(11) . . . . ?
C5 C6 C7 N3 0.2(10) . . . . ?
N1 C9 C10 C13 -0.5(11) . . . . ?
N1 C11 C12 C13 -3.2(9) . . . . ?
N1 C11 C12 C2 177.3(6) . . . 6 ?
C9 C10 C13 C12 -2.3(11) . . . . ?
C11 C12 C13 C10 3.9(10) . . . . ?
C2 C12 C13 C10 -176.6(6) 6 . . . ?
O1 C14 C15 C20 152.2(6) . . . . ?
O2 C14 C15 C20 -29.9(8) . . . . ?
O1 C14 C15 C16 -27.6(8) . . . . ?
O2 C14 C15 C16 150.3(6) . . . . ?
C20 C15 C16 C17 4.6(9) . . . . ?
C14 C15 C16 C17 -175.6(5) . . . . ?
C15 C16 C17 C18 -3.1(9) . . . . ?
C15 C16 C17 C8 176.3(5) . . . 5 ?
C16 C17 C18 C19 -0.8(9) . . . . ?
C8 C17 C18 C19 179.8(5) 5 . . . ?
C17 C18 C19 C20 3.2(9) . . . . ?
C17 C18 C19 C21 -178.8(5) . . . 4_545 ?
C18 C19 C20 C15 -1.6(9) . . . . ?
C21 C19 C20 C15 -179.6(5) 4_545 . . . ?
C16 C15 C20 C19 -2.2(9) . . . . ?
C14 C15 C20 C19 178.0(5) . . . . ?
C12 C11 N1 C9 0.5(9) . . . . ?
C12 C11 N1 Zn1 179.1(5) . . . . ?
C10 C9 N1 C11 1.4(10) . . . . ?
C10 C9 N1 Zn1 -177.1(5) . . . . ?
N3 C3 N2 C1 0.4(7) . . . . ?
C4 C3 N2 C1 179.7(6) . . . . ?
N3 C3 N2 Zn2 167.2(4) . . . . ?
C4 C3 N2 Zn2 -13.4(10) . . . . ?
C2 C1 N2 C3 -1.3(7) . . . . ?
C2 C1 N2 Zn2 -167.7(4) . . . . ?
N2 C3 N3 C7 -173.4(5) . . . . ?
C4 C3 N3 C7 7.2(9) . . . . ?
N2 C3 N3 C2 0.6(7) . . . . ?
C4 C3 N3 C2 -178.8(6) . . . . ?
C6 C7 N3 C3 -5.8(9) . . . . ?
C6 C7 N3 C2 -178.2(6) . . . . ?
C1 C2 N3 C3 -1.3(6) . . . . ?
C12 C2 N3 C3 -178.6(5) 6_556 . . . ?
C1 C2 N3 C7 171.9(6) . . . . ?
C12 C2 N3 C7 -5.3(10) 6_556 . . . ?
O2 C14 O1 Zn1 13.7(9) . . . . ?
C15 C14 O1 Zn1 -168.5(4) . . . . ?
O1 C14 O2 Zn2 -2.5(9) . . . . ?
C15 C14 O2 Zn2 179.7(4) . . . . ?
O4 C21 O3 Zn1 10.3(11) . . . . ?
C19 C21 O3 Zn1 -170.0(5) 4 . . . ?
O3 C21 O4 Zn2 4.6(9) . . . . ?
C19 C21 O4 Zn2 -175.1(4) 4 . . . ?
O7 C8 O6 Zn1 -28.2(9) . . . . ?
C17 C8 O6 Zn1 147.7(4) 5 . . . ?
Zn2 O5 Zn1 O6 140.33(18) . . . . ?
Zn2 O5 Zn1 O6 7.7(2) 2 . . . ?
Zn1 O5 Zn1 O6 -101.33(13) 2 . . . ?
Zn2 O5 Zn1 O1 56.49(19) . . . . ?
Zn2 O5 Zn1 O1 -76.2(2) 2 . . . ?
Zn1 O5 Zn1 O1 174.83(12) 2 . . . ?
Zn2 O5 Zn1 O3 -33.5(2) . . . . ?
Zn2 O5 Zn1 O3 -166.1(2) 2 . . . ?
Zn1 O5 Zn1 O3 84.87(15) 2 . . . ?
Zn2 O5 Zn1 O8 -118.34(14) . . . . ?
Zn2 O5 Zn1 O8 109.01(19) 2 . . . ?
Zn1 O5 Zn1 O8 0.0 2 . . . ?
Zn2 O5 Zn1 Zn2 -132.7(3) 2 . . . ?
Zn1 O5 Zn1 Zn2 118.34(14) 2 . . . ?
C8 O6 Zn1 O5 117.6(5) . . . . ?
C8 O6 Zn1 O1 -144.8(5) . . . . ?
C8 O6 Zn1 O3 -85.7(8) . . . . ?
C8 O6 Zn1 N1 -53.8(5) . . . . ?
C8 O6 Zn1 O8 37.8(5) . . . . ?
C8 O6 Zn1 Zn2 145.9(4) . . . . ?
C14 O1 Zn1 O5 -44.9(5) . . . . ?
C14 O1 Zn1 O6 -138.3(5) . . . . ?
C14 O1 Zn1 O3 55.1(5) . . . . ?
C14 O1 Zn1 N1 137.0(5) . . . . ?
C14 O1 Zn1 Zn2 -12.5(5) . . . . ?
C21 O3 Zn1 O5 8.7(7) . . . . ?
C21 O3 Zn1 O6 -147.7(7) . . . . ?
C21 O3 Zn1 O1 -89.2(7) . . . . ?
C21 O3 Zn1 N1 -179.8(7) . . . . ?
C21 O3 Zn1 O8 87.0(7) . . . . ?
C21 O3 Zn1 Zn2 -13.2(6) . . . . ?
C11 N1 Zn1 O6 -64.0(4) . . . . ?
C9 N1 Zn1 O6 114.5(5) . . . . ?
C11 N1 Zn1 O1 19.3(4) . . . . ?
C9 N1 Zn1 O1 -162.3(5) . . . . ?
C11 N1 Zn1 O3 107.8(5) . . . . ?
C9 N1 Zn1 O3 -73.8(5) . . . . ?
C11 N1 Zn1 O8 -165.7(4) . . . . ?
C9 N1 Zn1 O8 12.7(5) . . . . ?
C11 N1 Zn1 Zn2 84.6(5) . . . . ?
C9 N1 Zn1 Zn2 -96.9(5) . . . . ?
Zn1 O8 Zn1 O5 0.0 2 . . . ?
Zn1 O8 Zn1 O6 92.15(13) 2 . . . ?
Zn1 O8 Zn1 O3 -100.84(13) 2 . . . ?
Zn1 O8 Zn1 N1 177.38(13) 2 . . . ?
Zn1 O8 Zn1 Zn2 -33.77(2) 2 . . . ?
Zn2 O5 Zn2 O4 179.15(16) 2 . . . ?
Zn1 O5 Zn2 O4 53.0(2) . . . . ?
Zn1 O5 Zn2 O4 -61.0(2) 2 . . . ?
Zn2 O5 Zn2 N2 -45.9(2) 2 . . . ?
Zn1 O5 Zn2 N2 -172.0(2) . . . . ?
Zn1 O5 Zn2 N2 73.9(3) 2 . . . ?
Zn2 O5 Zn2 O2 71.81(15) 2 . . . ?
Zn1 O5 Zn2 O2 -54.3(2) . . . . ?
Zn1 O5 Zn2 O2 -168.4(2) 2 . . . ?
Zn2 O5 Zn2 Zn1 126.13(13) 2 . . . ?
Zn1 O5 Zn2 Zn1 -114.1(3) 2 . . . ?
C21 O4 Zn2 O5 -41.8(5) . . . . ?
C21 O4 Zn2 N2 173.8(5) . . . . ?
C21 O4 Zn2 O2 71.9(5) . . . . ?
C21 O4 Zn2 Zn1 -9.6(4) . . . . ?
C3 N2 Zn2 O5 155.4(4) . . . . ?
C1 N2 Zn2 O5 -40.6(6) . . . . ?
C3 N2 Zn2 O4 -64.0(5) . . . . ?
C1 N2 Zn2 O4 99.9(5) . . . . ?
C3 N2 Zn2 O2 34.5(5) . . . . ?
C1 N2 Zn2 O2 -161.6(5) . . . . ?
C3 N2 Zn2 Zn1 131.4(6) . . . . ?
C1 N2 Zn2 Zn1 -64.7(10) . . . . ?
C14 O2 Zn2 O5 28.3(6) . . . . ?
C14 O2 Zn2 O4 -94.5(5) . . . . ?
C14 O2 Zn2 N2 161.9(5) . . . . ?
C14 O2 Zn2 Zn1 -5.0(5) . . . . ?
O6 Zn1 Zn2 O5 -49.1(2) . . . . ?
O1 Zn1 Zn2 O5 -121.9(2) . . . . ?
O3 Zn1 Zn2 O5 144.1(2) . . . . ?
N1 Zn1 Zn2 O5 169.0(3) . . . . ?
O8 Zn1 Zn2 O5 60.9(2) . . . . ?
O5 Zn1 Zn2 O4 -135.5(2) . . . . ?
O6 Zn1 Zn2 O4 175.4(2) . . . . ?
O1 Zn1 Zn2 O4 102.55(19) . . . . ?
O3 Zn1 Zn2 O4 8.6(2) . . . . ?
N1 Zn1 Zn2 O4 33.4(3) . . . . ?
O8 Zn1 Zn2 O4 -74.68(16) . . . . ?
O5 Zn1 Zn2 N2 29.4(7) . . . . ?
O6 Zn1 Zn2 N2 -19.6(7) . . . . ?
O1 Zn1 Zn2 N2 -92.5(7) . . . . ?
O3 Zn1 Zn2 N2 173.5(7) . . . . ?
N1 Zn1 Zn2 N2 -161.6(7) . . . . ?
O8 Zn1 Zn2 N2 90.3(7) . . . . ?
O5 Zn1 Zn2 O2 128.5(2) . . . . ?
O6 Zn1 Zn2 O2 79.4(2) . . . . ?
O1 Zn1 Zn2 O2 6.57(18) . . . . ?
O3 Zn1 Zn2 O2 -87.4(2) . . . . ?
N1 Zn1 Zn2 O2 -62.6(3) . . . . ?
O8 Zn1 Zn2 O2 -170.66(17) . . . . ?

_diffrn_measured_fraction_theta_max 0.998
_diffrn_reflns_theta_full        26.50
_diffrn_measured_fraction_theta_full 0.998
_refine_diff_density_max         1.308
_refine_diff_density_min         -1.997
_refine_diff_density_rms         0.186
_diffrn_standards_number         0
_diffrn_standards_interval_count 0
_diffrn_standards_interval_time  0
_diffrn_standards_decay_%        0

_exptl_crystal_preparation       Luminescent
_database_code_depnum_ccdc_archive 'CCDC 1012147'
