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

#######################################################################
#
#                 Cambridge Crystallographic Data Centre
#                                CCDC 
# 
#######################################################################
# 
#  This CIF contains data from an original supplementary publication
#  deposited with the CCDC, and may include chemical, crystal,
#  experimental, refinement, atomic coordinates,
#  anisotropic displacement parameters and molecular geometry data,
#  as required by the journal to which it was submitted.
#
#  This CIF is provided on the understanding that it is used for bona
#  fide research purposes only. It may contain copyright material
#  of the CCDC or of third parties, and may not be copied or further
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#  except for the purpose of generating routine backup copies
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#  data retrieval see:
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#
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#  from this site to visualise CIF-encoded structures and 
#  to carry out CIF format checking respectively.
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data_1

#==========================================================================  

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C32 H28 N2 O4 Zn'
_chemical_formula_sum            'C32 H28 N2 O4 Zn'
_chemical_formula_weight         569.95

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'

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

_cell_length_a                   9.4258(19)
_cell_length_b                   10.052(2)
_cell_length_c                   15.309(3)
_cell_angle_alpha                97.47(3)
_cell_angle_beta                 105.32(3)
_cell_angle_gamma                103.94(3)
_cell_volume                     1328.4(6)
_cell_formula_units_Z            2
_cell_measurement_temperature    223(2)
_cell_measurement_reflns_used    ?
_cell_measurement_theta_min      ?
_cell_measurement_theta_max      ?

_exptl_crystal_description       blcok
_exptl_crystal_colour            yellow
_exptl_crystal_size_max          0.30
_exptl_crystal_size_mid          0.25
_exptl_crystal_size_min          0.25
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.425
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             592
_exptl_absorpt_coefficient_mu    0.966
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.7604
_exptl_absorpt_correction_T_max  0.7943
_exptl_absorpt_process_details   'Sadabs, (Sheldrick 2001)'
_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      223(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         0
_diffrn_standards_interval_count 0
_diffrn_standards_interval_time  0
_diffrn_standards_decay_%        0
_diffrn_reflns_number            11832
_diffrn_reflns_av_R_equivalents  0.0232
_diffrn_reflns_av_sigmaI/netI    0.0250
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_theta_min         1.41
_diffrn_reflns_theta_max         25.05
_reflns_number_total             4688
_reflns_number_gt                4253
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'Bruker SMART'
_computing_cell_refinement       'Bruker SMART'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXTL (Sheldrick, 2008)'
_computing_structure_refinement  SHELXTL
_computing_molecular_graphics    Diamond
_computing_publication_material  'SHELXTL and PLATON (Spek, 2009)'

_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)+(0.0634P)²+1.1526P] 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         4688
_refine_ls_number_parameters     356
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0438
_refine_ls_R_factor_gt           0.0395
_refine_ls_wR_factor_ref         0.1154
_refine_ls_wR_factor_gt          0.1114
_refine_ls_goodness_of_fit_ref   1.069
_refine_ls_restrained_S_all      1.069
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
Zn1 Zn 0.65508(4) 0.87812(3) 0.54165(2) 0.03102(13) Uani 1 1 d . . .
N1 N 0.6967(2) 0.8552(2) 0.40875(15) 0.0264(4) Uani 1 1 d . . .
N2 N 1.5749(3) 0.8713(2) -0.33713(16) 0.0304(5) Uani 1 1 d . . .
O1 O 0.6485(2) 0.66472(19) 0.53526(13) 0.0305(4) Uani 1 1 d . . .
O2 O 0.8778(2) 0.81494(18) 0.59967(14) 0.0358(4) Uani 1 1 d . . .
O3 O 0.5718(2) 0.16150(19) 0.53677(15) 0.0358(5) Uani 1 1 d . . .
O4 O 0.7736(2) 0.08182(17) 0.57857(13) 0.0288(4) Uani 1 1 d . . .
C1 C 0.6145(3) 0.7372(3) 0.34520(19) 0.0322(6) Uani 1 1 d . . .
H1 H 0.5325 0.6762 0.3573 0.039 Uiso 1 1 calc R . .
C2 C 0.6444(3) 0.7014(3) 0.26349(19) 0.0344(6) Uani 1 1 d . . .
H2 H 0.5827 0.6184 0.2209 0.041 Uiso 1 1 calc R . .
C3 C 0.7661(3) 0.7883(3) 0.24418(19) 0.0337(6) Uani 1 1 d . . .
C4 C 0.8485(3) 0.9129(3) 0.30848(19) 0.0318(6) Uani 1 1 d . . .
H4 H 0.9290 0.9770 0.2971 0.038 Uiso 1 1 calc R . .
C5 C 0.8110(3) 0.9417(3) 0.38927(18) 0.0293(5) Uani 1 1 d . . .
H5 H 0.8684 1.0255 0.4322 0.035 Uiso 1 1 calc R . .
C6 C 0.8066(4) 0.7462(4) 0.1606(2) 0.0412(7) Uani 1 1 d . . .
H6 H 0.7272 0.6917 0.1077 0.049 Uiso 1 1 calc R . .
C7 C 0.9468(4) 0.7803(3) 0.1556(2) 0.0409(7) Uani 1 1 d . . .
H7 H 1.0234 0.8316 0.2106 0.049 Uiso 1 1 calc R . .
C8 C 1.0016(3) 0.7489(3) 0.0745(2) 0.0384(7) Uani 1 1 d . . .
C9 C 1.1236(3) 0.6896(3) 0.08621(19) 0.0383(7) Uani 1 1 d . . .
C10 C 1.1962(3) 0.6804(3) 0.0177(2) 0.0390(7) Uani 1 1 d . . .
C11 C 1.1434(3) 0.7308(3) -0.06290(19) 0.0388(7) Uani 1 1 d . . .
C12 C 1.0122(4) 0.7763(3) -0.0786(2) 0.0402(7) Uani 1 1 d . . .
C13 C 0.9407(4) 0.7878(4) -0.0098(2) 0.0412(7) Uani 1 1 d . . .
C14 C 1.2302(4) 0.7346(4) -0.1314(2) 0.0445(8) Uani 1 1 d . . .
H14 H 1.2054 0.6531 -0.1768 0.053 Uiso 1 1 calc R . .
C15 C 1.3386(4) 0.8435(3) -0.1332(2) 0.0430(7) Uani 1 1 d . . .
H15 H 1.3636 0.9239 -0.0868 0.052 Uiso 1 1 calc R . .
C16 C 1.4246(3) 0.8518(3) -0.2006(2) 0.0348(6) Uani 1 1 d . . .
C17 C 1.4295(4) 0.7336(3) -0.2566(2) 0.0392(7) Uani 1 1 d . . .
H17 H 1.3825 0.6440 -0.2491 0.047 Uiso 1 1 calc R . .
C18 C 1.5033(3) 0.7476(3) -0.3232(2) 0.0376(6) Uani 1 1 d . . .
H18 H 1.5031 0.6657 -0.3608 0.045 Uiso 1 1 calc R . .
C19 C 1.5758(4) 0.9846(3) -0.2813(2) 0.0456(8) Uani 1 1 d . . .
H19 H 1.6275 1.0728 -0.2886 0.055 Uiso 1 1 calc R . .
C20 C 1.5044(4) 0.9797(3) -0.2127(2) 0.0493(8) Uani 1 1 d . . .
H20 H 1.5103 1.0632 -0.1744 0.059 Uiso 1 1 calc R . .
C21 C 1.1759(4) 0.6320(4) 0.1721(2) 0.0476(8) Uani 1 1 d . . .
H21A H 1.1181 0.6503 0.2138 0.071 Uiso 1 1 calc R . .
H21B H 1.2845 0.6772 0.2028 0.071 Uiso 1 1 calc R . .
H21C H 1.1586 0.5318 0.1545 0.071 Uiso 1 1 calc R . .
C22 C 1.3284(4) 0.6192(4) 0.0303(2) 0.0551(9) Uani 1 1 d . . .
H22A H 1.4163 0.6812 0.0794 0.083 Uiso 1 1 calc R . .
H22B H 1.3545 0.6083 -0.0269 0.083 Uiso 1 1 calc R . .
H22C H 1.3000 0.5284 0.0464 0.083 Uiso 1 1 calc R . .
C23 C 0.9465(4) 0.8160(4) -0.1703(2) 0.0556(9) Uani 1 1 d . . .
H23A H 0.8368 0.7703 -0.1941 0.083 Uiso 1 1 calc R . .
H23B H 0.9958 0.7861 -0.2144 0.083 Uiso 1 1 calc R . .
H23C H 0.9650 0.9167 -0.1608 0.083 Uiso 1 1 calc R . .
C24 C 0.8056(4) 0.8473(5) -0.0260(3) 0.0569(9) Uani 1 1 d . . .
H24A H 0.8253 0.9263 -0.0557 0.085 Uiso 1 1 calc R . .
H24B H 0.7908 0.8780 0.0329 0.085 Uiso 1 1 calc R . .
H24C H 0.7139 0.7758 -0.0654 0.085 Uiso 1 1 calc R . .
C25 C 0.8573(3) 0.5714(2) 0.58668(16) 0.0232(5) Uani 1 1 d . . .
C26 C 1.0147(3) 0.5926(3) 0.61274(19) 0.0294(5) Uani 1 1 d . . .
H26 H 1.0815 0.6838 0.6260 0.035 Uiso 1 1 calc R . .
C27 C 1.0739(3) 0.4786(3) 0.6192(2) 0.0315(6) Uani 1 1 d . . .
H27 H 1.1806 0.4928 0.6353 0.038 Uiso 1 1 calc R . .
C28 C 0.9762(3) 0.3447(3) 0.60204(18) 0.0278(5) Uani 1 1 d . . .
H28 H 1.0167 0.2681 0.6064 0.033 Uiso 1 1 calc R . .
C29 C 0.8178(3) 0.3230(2) 0.57826(16) 0.0216(5) Uani 1 1 d . . .
C30 C 0.7587(3) 0.4368(2) 0.56893(16) 0.0213(5) Uani 1 1 d . . .
H30 H 0.6519 0.4224 0.5506 0.026 Uiso 1 1 calc R . .
C31 C 0.7919(3) 0.6920(3) 0.57369(17) 0.0266(5) Uani 1 1 d . . .
C32 C 0.7118(3) 0.1782(2) 0.56181(16) 0.0218(5) Uani 1 1 d . . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Zn1 O4 2.0059(19) 1_565 ?
Zn1 O3 2.070(2) 2_666 ?
Zn1 O1 2.1197(18) . ?
Zn1 N1 2.166(2) . ?
Zn1 N2 2.184(2) 1_456 ?
Zn1 O2 2.324(2) . ?
Zn1 C31 2.544(3) . ?
N1 C5 1.338(3) . ?
N1 C1 1.347(4) . ?
N2 C19 1.329(4) . ?
N2 C18 1.337(4) . ?
N2 Zn1 2.184(2) 1_654 ?
O1 C31 1.268(3) . ?
O2 C31 1.249(3) . ?
O3 C32 1.235(3) . ?
O3 Zn1 2.070(2) 2_666 ?
O4 C32 1.266(3) . ?
O4 Zn1 2.0059(19) 1_545 ?
C1 C2 1.375(4) . ?
C1 H1 0.9400 . ?
C2 C3 1.389(4) . ?
C2 H2 0.9400 . ?
C3 C4 1.395(4) . ?
C3 C6 1.468(4) . ?
C4 C5 1.387(4) . ?
C4 H4 0.9400 . ?
C5 H5 0.9400 . ?
C6 C7 1.309(4) . ?
C6 H6 0.9400 . ?
C7 C8 1.490(4) . ?
C7 H7 0.9400 . ?
C8 C9 1.400(4) . ?
C8 C13 1.413(4) . ?
C9 C10 1.400(4) . ?
C9 C21 1.516(4) . ?
C10 C11 1.410(4) . ?
C10 C22 1.497(4) . ?
C11 C12 1.393(4) . ?
C11 C14 1.490(4) . ?
C12 C13 1.400(4) . ?
C12 C23 1.522(4) . ?
C13 C24 1.510(5) . ?
C14 C15 1.314(5) . ?
C14 H14 0.9400 . ?
C15 C16 1.470(4) . ?
C15 H15 0.9400 . ?
C16 C20 1.386(4) . ?
C16 C17 1.389(4) . ?
C17 C18 1.382(4) . ?
C17 H17 0.9400 . ?
C18 H18 0.9400 . ?
C19 C20 1.388(4) . ?
C19 H19 0.9400 . ?
C20 H20 0.9400 . ?
C21 H21A 0.9700 . ?
C21 H21B 0.9700 . ?
C21 H21C 0.9700 . ?
C22 H22A 0.9700 . ?
C22 H22B 0.9700 . ?
C22 H22C 0.9700 . ?
C23 H23A 0.9700 . ?
C23 H23B 0.9700 . ?
C23 H23C 0.9700 . ?
C24 H24A 0.9700 . ?
C24 H24B 0.9700 . ?
C24 H24C 0.9700 . ?
C25 C26 1.385(4) . ?
C25 C30 1.390(4) . ?
C25 C31 1.499(3) . ?
C26 C27 1.394(4) . ?
C26 H26 0.9400 . ?
C27 C28 1.383(4) . ?
C27 H27 0.9400 . ?
C28 C29 1.394(4) . ?
C28 H28 0.9400 . ?
C29 C30 1.396(3) . ?
C29 C32 1.500(3) . ?
C30 H30 0.9400 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
O4 Zn1 O3 114.16(8) 1_565 2_666 ?
O4 Zn1 O1 150.12(8) 1_565 . ?
O3 Zn1 O1 95.52(8) 2_666 . ?
O4 Zn1 N1 92.82(9) 1_565 . ?
O3 Zn1 N1 84.27(9) 2_666 . ?
O1 Zn1 N1 86.57(8) . . ?
O4 Zn1 N2 96.14(9) 1_565 1_456 ?
O3 Zn1 N2 87.44(9) 2_666 1_456 ?
O1 Zn1 N2 88.16(8) . 1_456 ?
N1 Zn1 N2 169.70(9) . 1_456 ?
O4 Zn1 O2 91.01(8) 1_565 . ?
O3 Zn1 O2 153.75(7) 2_666 . ?
O1 Zn1 O2 59.11(7) . . ?
N1 Zn1 O2 87.33(8) . . ?
N2 Zn1 O2 97.54(8) 1_456 . ?
O4 Zn1 C31 120.31(9) 1_565 . ?
O3 Zn1 C31 125.04(9) 2_666 . ?
O1 Zn1 C31 29.81(8) . . ?
N1 Zn1 C31 86.36(8) . . ?
N2 Zn1 C31 93.44(8) 1_456 . ?
O2 Zn1 C31 29.30(8) . . ?
C5 N1 C1 117.3(2) . . ?
C5 N1 Zn1 124.42(18) . . ?
C1 N1 Zn1 117.77(17) . . ?
C19 N2 C18 116.5(2) . . ?
C19 N2 Zn1 123.69(19) . 1_654 ?
C18 N2 Zn1 119.29(19) . 1_654 ?
C31 O1 Zn1 93.95(15) . . ?
C31 O2 Zn1 85.13(16) . . ?
C32 O3 Zn1 163.83(19) . 2_666 ?
C32 O4 Zn1 122.77(17) . 1_545 ?
N1 C1 C2 123.3(3) . . ?
N1 C1 H1 118.4 . . ?
C2 C1 H1 118.4 . . ?
C1 C2 C3 119.8(3) . . ?
C1 C2 H2 120.1 . . ?
C3 C2 H2 120.1 . . ?
C2 C3 C4 117.1(2) . . ?
C2 C3 C6 120.3(3) . . ?
C4 C3 C6 122.6(3) . . ?
C5 C4 C3 119.6(3) . . ?
C5 C4 H4 120.2 . . ?
C3 C4 H4 120.2 . . ?
N1 C5 C4 122.9(3) . . ?
N1 C5 H5 118.6 . . ?
C4 C5 H5 118.6 . . ?
C7 C6 C3 123.8(3) . . ?
C7 C6 H6 118.1 . . ?
C3 C6 H6 118.1 . . ?
C6 C7 C8 128.9(3) . . ?
C6 C7 H7 115.5 . . ?
C8 C7 H7 115.5 . . ?
C9 C8 C13 120.5(3) . . ?
C9 C8 C7 118.2(3) . . ?
C13 C8 C7 121.1(3) . . ?
C10 C9 C8 120.2(3) . . ?
C10 C9 C21 119.5(3) . . ?
C8 C9 C21 120.3(3) . . ?
C9 C10 C11 118.8(3) . . ?
C9 C10 C22 120.6(3) . . ?
C11 C10 C22 120.6(3) . . ?
C12 C11 C10 120.8(3) . . ?
C12 C11 C14 120.3(3) . . ?
C10 C11 C14 119.0(3) . . ?
C11 C12 C13 120.3(3) . . ?
C11 C12 C23 120.4(3) . . ?
C13 C12 C23 119.4(3) . . ?
C12 C13 C8 118.8(3) . . ?
C12 C13 C24 119.2(3) . . ?
C8 C13 C24 121.9(3) . . ?
C15 C14 C11 124.9(3) . . ?
C15 C14 H14 117.5 . . ?
C11 C14 H14 117.5 . . ?
C14 C15 C16 126.4(3) . . ?
C14 C15 H15 116.8 . . ?
C16 C15 H15 116.8 . . ?
C20 C16 C17 116.1(3) . . ?
C20 C16 C15 121.4(3) . . ?
C17 C16 C15 122.5(3) . . ?
C18 C17 C16 120.2(3) . . ?
C18 C17 H17 119.9 . . ?
C16 C17 H17 119.9 . . ?
N2 C18 C17 123.5(3) . . ?
N2 C18 H18 118.2 . . ?
C17 C18 H18 118.2 . . ?
N2 C19 C20 123.6(3) . . ?
N2 C19 H19 118.2 . . ?
C20 C19 H19 118.2 . . ?
C16 C20 C19 120.0(3) . . ?
C16 C20 H20 120.0 . . ?
C19 C20 H20 120.0 . . ?
C9 C21 H21A 109.5 . . ?
C9 C21 H21B 109.5 . . ?
H21A C21 H21B 109.5 . . ?
C9 C21 H21C 109.5 . . ?
H21A C21 H21C 109.5 . . ?
H21B C21 H21C 109.5 . . ?
C10 C22 H22A 109.5 . . ?
C10 C22 H22B 109.5 . . ?
H22A C22 H22B 109.5 . . ?
C10 C22 H22C 109.5 . . ?
H22A C22 H22C 109.5 . . ?
H22B C22 H22C 109.5 . . ?
C12 C23 H23A 109.5 . . ?
C12 C23 H23B 109.5 . . ?
H23A C23 H23B 109.5 . . ?
C12 C23 H23C 109.5 . . ?
H23A C23 H23C 109.5 . . ?
H23B C23 H23C 109.5 . . ?
C13 C24 H24A 109.5 . . ?
C13 C24 H24B 109.5 . . ?
H24A C24 H24B 109.5 . . ?
C13 C24 H24C 109.5 . . ?
H24A C24 H24C 109.5 . . ?
H24B C24 H24C 109.5 . . ?
C26 C25 C30 120.0(2) . . ?
C26 C25 C31 120.4(2) . . ?
C30 C25 C31 119.6(2) . . ?
C25 C26 C27 119.9(2) . . ?
C25 C26 H26 120.0 . . ?
C27 C26 H26 120.0 . . ?
C28 C27 C26 120.3(2) . . ?
C28 C27 H27 119.9 . . ?
C26 C27 H27 119.9 . . ?
C27 C28 C29 120.1(2) . . ?
C27 C28 H28 119.9 . . ?
C29 C28 H28 119.9 . . ?
C28 C29 C30 119.4(2) . . ?
C28 C29 C32 120.3(2) . . ?
C30 C29 C32 120.3(2) . . ?
C25 C30 C29 120.2(2) . . ?
C25 C30 H30 119.9 . . ?
C29 C30 H30 119.9 . . ?
O2 C31 O1 121.8(2) . . ?
O2 C31 C25 120.3(2) . . ?
O1 C31 C25 117.9(2) . . ?
O2 C31 Zn1 65.57(14) . . ?
O1 C31 Zn1 56.23(12) . . ?
C25 C31 Zn1 174.1(2) . . ?
O3 C32 O4 124.4(2) . . ?
O3 C32 C29 118.7(2) . . ?
O4 C32 C29 116.8(2) . . ?

_diffrn_measured_fraction_theta_max 0.997
_diffrn_reflns_theta_full        25.05
_diffrn_measured_fraction_theta_full 0.997
_refine_diff_density_max         0.520
_refine_diff_density_min         -0.467
_refine_diff_density_rms         0.070
_database_code_depnum_ccdc_archive 'CCDC 977633'
#######################################################################
#
#                 Cambridge Crystallographic Data Centre
#                                CCDC 
# 
#######################################################################
# 
#  This CIF contains data from an original supplementary publication
#  deposited with the CCDC, and may include chemical, crystal,
#  experimental, refinement, atomic coordinates,
#  anisotropic displacement parameters and molecular geometry data,
#  as required by the journal to which it was submitted.
#
#  This CIF is provided on the understanding that it is used for bona
#  fide research purposes only. It may contain copyright material
#  of the CCDC or of third parties, and may not be copied or further
#  disseminated in any form, whether machine-readable or not,
#  except for the purpose of generating routine backup copies
#  on your local computer system.
# 
#  For further information on the CCDC, data deposition and
#  data retrieval see:
#                         www.ccdc.cam.ac.uk
#
#  Bona fide researchers may freely download Mercury and enCIFer
#  from this site to visualise CIF-encoded structures and 
#  to carry out CIF format checking respectively.
#
data_2

#==========================================================================

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         '2(C32 H27 Cl N2 O4 Zn), C2 H3 N'
_chemical_formula_sum            'C66 H57 Cl2 N5 O8 Zn2'
_chemical_formula_weight         1249.85

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'
Cl Cl 0.1484 0.1585 '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'

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

_cell_length_a                   9.907(2)
_cell_length_b                   10.421(2)
_cell_length_c                   16.142(3)
_cell_angle_alpha                81.18(3)
_cell_angle_beta                 75.18(3)
_cell_angle_gamma                81.78(3)
_cell_volume                     1582.6(6)
_cell_formula_units_Z            1
_cell_measurement_temperature    223(2)
_cell_measurement_reflns_used    ?
_cell_measurement_theta_min      ?
_cell_measurement_theta_max      ?

_exptl_crystal_description       block
_exptl_crystal_colour            yellow
_exptl_crystal_size_max          0.40
_exptl_crystal_size_mid          0.35
_exptl_crystal_size_min          0.30
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.311
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             646
_exptl_absorpt_coefficient_mu    0.899
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.7150
_exptl_absorpt_correction_T_max  0.7742
_exptl_absorpt_process_details   'Sadabs, (Sheldrick 2001)'
_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      223(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         0
_diffrn_standards_interval_count 0
_diffrn_standards_interval_time  0
_diffrn_standards_decay_%        0
_diffrn_reflns_number            11088
_diffrn_reflns_av_R_equivalents  0.0406
_diffrn_reflns_av_sigmaI/netI    0.0638
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_theta_min         2.14
_diffrn_reflns_theta_max         25.05
_reflns_number_total             5580
_reflns_number_gt                4483
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'Bruker SMART'
_computing_cell_refinement       'Bruker SMART'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXTL (Sheldrick, 2008)'
_computing_structure_refinement  SHELXTL
_computing_molecular_graphics    Diamond
_computing_publication_material  'SHELXTL and PLATON (Spek, 2009)'

_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)+(0.0809P)²+0.3975P] 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         5580
_refine_ls_number_parameters     393
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0670
_refine_ls_R_factor_gt           0.0513
_refine_ls_wR_factor_ref         0.1410
_refine_ls_wR_factor_gt          0.1301
_refine_ls_goodness_of_fit_ref   1.037
_refine_ls_restrained_S_all      1.037
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
Zn1 Zn 0.34927(3) 0.88090(3) 0.53832(2) 0.02934(15) Uani 1 1 d . . .
N1 N 0.4495(3) 0.7882(3) 0.42479(18) 0.0346(7) Uani 1 1 d . . .
N2 N 1.2674(3) -0.0271(3) -0.34613(18) 0.0408(7) Uani 1 1 d . . .
O1 O 0.5067(2) 0.7822(2) 0.59213(15) 0.0375(6) Uani 1 1 d . . .
O2 O 0.6411(3) 0.9396(2) 0.53422(17) 0.0471(7) Uani 1 1 d . . .
O3 O 1.2299(2) 0.6870(3) 0.59553(18) 0.0571(8) Uani 1 1 d . . .
O4 O 1.1490(2) 0.8668(3) 0.52719(18) 0.0510(7) Uani 1 1 d . . .
C1 C 0.4505(4) 0.8430(4) 0.3439(2) 0.0459(9) Uani 1 1 d . . .
H1 H 0.4107 0.9300 0.3354 0.055 Uiso 1 1 calc R . .
C2 C 0.5068(5) 0.7781(4) 0.2732(3) 0.0534(11) Uani 1 1 d . . .
H2 H 0.5043 0.8206 0.2178 0.064 Uiso 1 1 calc R . .
C3 C 0.5673(4) 0.6499(4) 0.2829(2) 0.0444(9) Uani 1 1 d . . .
C4 C 0.5683(4) 0.5941(3) 0.3668(2) 0.0431(9) Uani 1 1 d . . .
H4 H 0.6104 0.5083 0.3771 0.052 Uiso 1 1 calc R . .
C5 C 0.5080(4) 0.6645(3) 0.4339(2) 0.0403(8) Uani 1 1 d . . .
H5 H 0.5075 0.6237 0.4901 0.048 Uiso 1 1 calc R . .
C6 C 0.6292(5) 0.5799(4) 0.2085(2) 0.0552(11) Uani 1 1 d . . .
H6 H 0.6213 0.6240 0.1543 0.066 Uiso 1 1 calc R . .
C7 C 0.6945(5) 0.4620(4) 0.2096(3) 0.0663(13) Uani 1 1 d . . .
H7 H 0.6977 0.4155 0.2639 0.080 Uiso 1 1 calc R . .
C8 C 0.7646(6) 0.3944(4) 0.1320(3) 0.0633(13) Uani 1 1 d . . .
C9 C 0.6869(6) 0.3578(5) 0.0802(3) 0.0708(14) Uani 1 1 d . . .
C10 C 0.7580(6) 0.3015(5) 0.0055(3) 0.0721(14) Uani 1 1 d . . .
C11 C 0.9052(6) 0.2828(4) -0.0158(3) 0.0668(14) Uani 1 1 d . . .
C12 C 0.9826(6) 0.3155(4) 0.0375(3) 0.0680(14) Uani 1 1 d . . .
C13 C 0.9110(6) 0.3702(4) 0.1128(3) 0.0666(14) Uani 1 1 d . . .
C14 C 0.9786(6) 0.2282(5) -0.0976(3) 0.0761(16) Uani 1 1 d . . .
H14 H 0.9545 0.2727 -0.1479 0.091 Uiso 1 1 calc R . .
C15 C 1.0719(5) 0.1265(5) -0.1084(3) 0.0683(14) Uani 1 1 d . . .
H15 H 1.0970 0.0810 -0.0586 0.082 Uiso 1 1 calc R . .
C16 C 1.1416(5) 0.0763(4) -0.1906(3) 0.0552(11) Uani 1 1 d . . .
C17 C 1.1393(5) 0.1482(5) -0.2699(3) 0.0693(14) Uani 1 1 d . . .
H17 H 1.0965 0.2347 -0.2727 0.083 Uiso 1 1 calc R . .
C18 C 1.1997(5) 0.0929(4) -0.3445(3) 0.0644(13) Uani 1 1 d . . .
H18 H 1.1931 0.1425 -0.3974 0.077 Uiso 1 1 calc R . .
C19 C 1.2780(4) -0.0911(4) -0.2695(3) 0.0575(12) Uani 1 1 d . . .
H19 H 1.3300 -0.1739 -0.2684 0.069 Uiso 1 1 calc R . .
C20 C 1.2182(5) -0.0438(4) -0.1926(3) 0.0627(13) Uani 1 1 d . . .
H20 H 1.2296 -0.0940 -0.1408 0.075 Uiso 1 1 calc R . .
C21 C 0.5288(6) 0.3723(6) 0.1070(4) 0.0944(18) Uani 1 1 d . . .
H21A H 0.4917 0.4353 0.0653 0.142 Uiso 1 1 calc R . .
H21B H 0.4979 0.4025 0.1635 0.142 Uiso 1 1 calc R . .
H21C H 0.4950 0.2886 0.1095 0.142 Uiso 1 1 calc R . .
C22 C 0.6787(7) 0.2595(7) -0.0513(4) 0.108(2) Uani 1 1 d . . .
H22A H 0.6121 0.2007 -0.0172 0.162 Uiso 1 1 calc R . .
H22B H 0.7441 0.2150 -0.0965 0.162 Uiso 1 1 calc R . .
H22C H 0.6287 0.3356 -0.0772 0.162 Uiso 1 1 calc R . .
C23 C 1.1418(6) 0.2998(6) 0.0150(3) 0.0898(18) Uani 1 1 d . . .
H23A H 1.1755 0.2226 0.0489 0.135 Uiso 1 1 calc R . .
H23B H 1.1752 0.3762 0.0275 0.135 Uiso 1 1 calc R . .
H23C H 1.1767 0.2907 -0.0459 0.135 Uiso 1 1 calc R . .
C24 C 0.9921(6) 0.4072(6) 0.1722(3) 0.0911(18) Uani 1 1 d . . .
H24A H 0.9311 0.4108 0.2296 0.137 Uiso 1 1 calc R . .
H24B H 1.0248 0.4921 0.1500 0.137 Uiso 1 1 calc R . .
H24C H 1.0720 0.3424 0.1750 0.137 Uiso 1 1 calc R . .
C25 C 0.7496(3) 0.7373(3) 0.5848(2) 0.0314(7) Uani 1 1 d . . .
C26 C 0.7369(3) 0.6073(3) 0.6151(3) 0.0440(9) Uani 1 1 d . . .
H26 H 0.6490 0.5752 0.6278 0.053 Uiso 1 1 calc R . .
C27 C 0.8549(4) 0.5247(4) 0.6266(3) 0.0530(11) Uani 1 1 d . . .
C28 C 0.9842(4) 0.5690(4) 0.6090(3) 0.0478(10) Uani 1 1 d . . .
H28 H 1.0634 0.5114 0.6166 0.057 Uiso 1 1 calc R . .
C29 C 0.9965(3) 0.7011(3) 0.5797(2) 0.0370(8) Uani 1 1 d . . .
C30 C 0.8798(3) 0.7828(3) 0.5657(2) 0.0331(7) Uani 1 1 d . . .
H30 H 0.8890 0.8706 0.5428 0.040 Uiso 1 1 calc R . .
C31 C 0.6231(3) 0.8272(3) 0.5690(2) 0.0302(7) Uani 1 1 d . . .
C32 C 1.1353(3) 0.7523(4) 0.5663(2) 0.0420(9) Uani 1 1 d . . .
Cl1 Cl 0.83818(13) 0.35964(12) 0.66104(13) 0.1058(6) Uani 1 1 d . . .
C33 C 0.1378(13) 1.0202(16) 0.2712(12) 0.132(6) Uani 0.50 1 d P . .
H33A H 0.0976 0.9531 0.2527 0.198 Uiso 0.50 1 calc PR . .
H33B H 0.0697 1.0967 0.2787 0.198 Uiso 0.50 1 calc PR . .
H33C H 0.1627 0.9875 0.3255 0.198 Uiso 0.50 1 calc PR . .
C34 C 0.2454(19) 1.0501(16) 0.2153(14) 0.119(6) Uani 0.50 1 d P . .
N3 N 0.344(2) 1.0686(18) 0.1693(14) 0.196(9) Uani 0.50 1 d P . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Zn1 O2 2.049(2) 2_676 ?
Zn1 O1 2.050(2) . ?
Zn1 O4 2.065(2) 1_455 ?
Zn1 N2 2.146(3) 1_466 ?
Zn1 N1 2.148(3) . ?
Zn1 O3 2.426(3) 1_455 ?
Zn1 C32 2.575(4) 1_455 ?
N1 C5 1.338(4) . ?
N1 C1 1.341(4) . ?
N2 C18 1.333(5) . ?
N2 C19 1.333(5) . ?
N2 Zn1 2.146(3) 1_644 ?
O1 C31 1.253(4) . ?
O2 C31 1.236(4) . ?
O2 Zn1 2.049(2) 2_676 ?
O3 C32 1.229(4) . ?
O3 Zn1 2.426(3) 1_655 ?
O4 C32 1.269(5) . ?
O4 Zn1 2.065(2) 1_655 ?
C1 C2 1.369(5) . ?
C1 H1 0.9400 . ?
C2 C3 1.387(5) . ?
C2 H2 0.9400 . ?
C3 C4 1.392(5) . ?
C3 C6 1.453(5) . ?
C4 C5 1.363(5) . ?
C4 H4 0.9400 . ?
C5 H5 0.9400 . ?
C6 C7 1.304(5) . ?
C6 H6 0.9400 . ?
C7 C8 1.494(6) . ?
C7 H7 0.9400 . ?
C8 C9 1.396(8) . ?
C8 C13 1.398(7) . ?
C9 C10 1.399(6) . ?
C9 C21 1.506(8) . ?
C10 C11 1.402(7) . ?
C10 C22 1.497(8) . ?
C11 C12 1.396(7) . ?
C11 C14 1.489(6) . ?
C12 C13 1.399(6) . ?
C12 C23 1.516(7) . ?
C13 C24 1.520(8) . ?
C14 C15 1.305(6) . ?
C14 H14 0.9400 . ?
C15 C16 1.468(5) . ?
C15 H15 0.9400 . ?
C16 C20 1.368(5) . ?
C16 C17 1.384(6) . ?
C17 C18 1.373(6) . ?
C17 H17 0.9400 . ?
C18 H18 0.9400 . ?
C19 C20 1.365(6) . ?
C19 H19 0.9400 . ?
C20 H20 0.9400 . ?
C21 H21A 0.9700 . ?
C21 H21B 0.9700 . ?
C21 H21C 0.9700 . ?
C22 H22A 0.9700 . ?
C22 H22B 0.9700 . ?
C22 H22C 0.9700 . ?
C23 H23A 0.9700 . ?
C23 H23B 0.9700 . ?
C23 H23C 0.9700 . ?
C24 H24A 0.9700 . ?
C24 H24B 0.9700 . ?
C24 H24C 0.9700 . ?
C25 C26 1.380(5) . ?
C25 C30 1.382(4) . ?
C25 C31 1.507(4) . ?
C26 C27 1.384(5) . ?
C26 H26 0.9400 . ?
C27 C28 1.370(5) . ?
C27 Cl1 1.743(4) . ?
C28 C29 1.398(5) . ?
C28 H28 0.9400 . ?
C29 C30 1.380(4) . ?
C29 C32 1.498(5) . ?
C30 H30 0.9400 . ?
C32 Zn1 2.575(4) 1_655 ?
C33 C34 1.25(2) . ?
C33 H33A 0.9700 . ?
C33 H33B 0.9700 . ?
C33 H33C 0.9700 . ?
C34 N3 1.09(2) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
O2 Zn1 O1 124.85(10) 2_676 . ?
O2 Zn1 O4 93.00(11) 2_676 1_455 ?
O1 Zn1 O4 142.15(10) . 1_455 ?
O2 Zn1 N2 90.28(11) 2_676 1_466 ?
O1 Zn1 N2 88.70(10) . 1_466 ?
O4 Zn1 N2 91.28(11) 1_455 1_466 ?
O2 Zn1 N1 90.11(11) 2_676 . ?
O1 Zn1 N1 86.89(10) . . ?
O4 Zn1 N1 93.79(11) 1_455 . ?
N2 Zn1 N1 174.89(10) 1_466 . ?
O2 Zn1 O3 150.14(10) 2_676 1_455 ?
O1 Zn1 O3 84.81(9) . 1_455 ?
O4 Zn1 O3 57.44(10) 1_455 1_455 ?
N2 Zn1 O3 94.19(11) 1_466 1_455 ?
N1 Zn1 O3 88.00(10) . 1_455 ?
O2 Zn1 C32 122.10(12) 2_676 1_455 ?
O1 Zn1 C32 113.01(11) . 1_455 ?
O4 Zn1 C32 29.18(11) 1_455 1_455 ?
N2 Zn1 C32 92.90(12) 1_466 1_455 ?
N1 Zn1 C32 91.21(11) . 1_455 ?
O3 Zn1 C32 28.25(10) 1_455 1_455 ?
C5 N1 C1 116.5(3) . . ?
C5 N1 Zn1 119.0(2) . . ?
C1 N1 Zn1 124.4(2) . . ?
C18 N2 C19 115.5(3) . . ?
C18 N2 Zn1 123.8(3) . 1_644 ?
C19 N2 Zn1 120.6(2) . 1_644 ?
C31 O1 Zn1 116.7(2) . . ?
C31 O2 Zn1 169.6(3) . 2_676 ?
C32 O3 Zn1 82.6(2) . 1_655 ?
C32 O4 Zn1 98.3(2) . 1_655 ?
N1 C1 C2 123.0(3) . . ?
N1 C1 H1 118.5 . . ?
C2 C1 H1 118.5 . . ?
C1 C2 C3 120.4(4) . . ?
C1 C2 H2 119.8 . . ?
C3 C2 H2 119.8 . . ?
C2 C3 C4 116.4(3) . . ?
C2 C3 C6 121.2(3) . . ?
C4 C3 C6 122.4(3) . . ?
C5 C4 C3 119.6(3) . . ?
C5 C4 H4 120.2 . . ?
C3 C4 H4 120.2 . . ?
N1 C5 C4 124.1(3) . . ?
N1 C5 H5 118.0 . . ?
C4 C5 H5 118.0 . . ?
C7 C6 C3 126.4(4) . . ?
C7 C6 H6 116.8 . . ?
C3 C6 H6 116.8 . . ?
C6 C7 C8 125.7(4) . . ?
C6 C7 H7 117.2 . . ?
C8 C7 H7 117.2 . . ?
C9 C8 C13 121.2(4) . . ?
C9 C8 C7 121.3(4) . . ?
C13 C8 C7 117.6(5) . . ?
C8 C9 C10 119.0(5) . . ?
C8 C9 C21 120.3(4) . . ?
C10 C9 C21 120.6(5) . . ?
C9 C10 C11 119.6(5) . . ?
C9 C10 C22 120.8(5) . . ?
C11 C10 C22 119.5(4) . . ?
C12 C11 C10 121.2(4) . . ?
C12 C11 C14 120.1(5) . . ?
C10 C11 C14 118.6(5) . . ?
C11 C12 C13 118.9(5) . . ?
C11 C12 C23 122.4(4) . . ?
C13 C12 C23 118.6(5) . . ?
C8 C13 C12 119.9(5) . . ?
C8 C13 C24 119.8(4) . . ?
C12 C13 C24 120.3(5) . . ?
C15 C14 C11 128.3(4) . . ?
C15 C14 H14 115.8 . . ?
C11 C14 H14 115.8 . . ?
C14 C15 C16 126.3(4) . . ?
C14 C15 H15 116.8 . . ?
C16 C15 H15 116.8 . . ?
C20 C16 C17 116.2(4) . . ?
C20 C16 C15 121.0(4) . . ?
C17 C16 C15 122.7(4) . . ?
C18 C17 C16 119.9(4) . . ?
C18 C17 H17 120.1 . . ?
C16 C17 H17 120.1 . . ?
N2 C18 C17 123.7(4) . . ?
N2 C18 H18 118.2 . . ?
C17 C18 H18 118.2 . . ?
N2 C19 C20 124.1(4) . . ?
N2 C19 H19 117.9 . . ?
C20 C19 H19 117.9 . . ?
C19 C20 C16 120.3(4) . . ?
C19 C20 H20 119.9 . . ?
C16 C20 H20 119.9 . . ?
C9 C21 H21A 109.5 . . ?
C9 C21 H21B 109.5 . . ?
H21A C21 H21B 109.5 . . ?
C9 C21 H21C 109.5 . . ?
H21A C21 H21C 109.5 . . ?
H21B C21 H21C 109.5 . . ?
C10 C22 H22A 109.5 . . ?
C10 C22 H22B 109.5 . . ?
H22A C22 H22B 109.5 . . ?
C10 C22 H22C 109.5 . . ?
H22A C22 H22C 109.5 . . ?
H22B C22 H22C 109.5 . . ?
C12 C23 H23A 109.5 . . ?
C12 C23 H23B 109.5 . . ?
H23A C23 H23B 109.5 . . ?
C12 C23 H23C 109.5 . . ?
H23A C23 H23C 109.5 . . ?
H23B C23 H23C 109.5 . . ?
C13 C24 H24A 109.5 . . ?
C13 C24 H24B 109.5 . . ?
H24A C24 H24B 109.5 . . ?
C13 C24 H24C 109.5 . . ?
H24A C24 H24C 109.5 . . ?
H24B C24 H24C 109.5 . . ?
C26 C25 C30 119.7(3) . . ?
C26 C25 C31 119.8(3) . . ?
C30 C25 C31 120.4(3) . . ?
C25 C26 C27 119.3(3) . . ?
C25 C26 H26 120.3 . . ?
C27 C26 H26 120.3 . . ?
C28 C27 C26 121.6(3) . . ?
C28 C27 Cl1 119.7(3) . . ?
C26 C27 Cl1 118.7(3) . . ?
C27 C28 C29 119.0(3) . . ?
C27 C28 H28 120.5 . . ?
C29 C28 H28 120.5 . . ?
C30 C29 C28 119.5(3) . . ?
C30 C29 C32 121.1(3) . . ?
C28 C29 C32 119.4(3) . . ?
C29 C30 C25 120.9(3) . . ?
C29 C30 H30 119.6 . . ?
C25 C30 H30 119.6 . . ?
O2 C31 O1 124.6(3) . . ?
O2 C31 C25 117.9(3) . . ?
O1 C31 C25 117.4(3) . . ?
O3 C32 O4 121.7(3) . . ?
O3 C32 C29 120.6(4) . . ?
O4 C32 C29 117.7(3) . . ?
O3 C32 Zn1 69.1(2) . 1_655 ?
O4 C32 Zn1 52.55(17) . 1_655 ?
C29 C32 Zn1 169.7(3) . 1_655 ?
C34 C33 H33A 109.5 . . ?
C34 C33 H33B 109.5 . . ?
H33A C33 H33B 109.5 . . ?
C34 C33 H33C 109.5 . . ?
H33A C33 H33C 109.5 . . ?
H33B C33 H33C 109.5 . . ?
N3 C34 C33 174.9(18) . . ?

_diffrn_measured_fraction_theta_max 0.996
_diffrn_reflns_theta_full        25.05
_diffrn_measured_fraction_theta_full 0.996
_refine_diff_density_max         0.704
_refine_diff_density_min         -0.888
_refine_diff_density_rms         0.084
_database_code_depnum_ccdc_archive 'CCDC 977634'
#######################################################################
#
#                 Cambridge Crystallographic Data Centre
#                                CCDC 
# 
#######################################################################
# 
#  This CIF contains data from an original supplementary publication
#  deposited with the CCDC, and may include chemical, crystal,
#  experimental, refinement, atomic coordinates,
#  anisotropic displacement parameters and molecular geometry data,
#  as required by the journal to which it was submitted.
#
#  This CIF is provided on the understanding that it is used for bona
#  fide research purposes only. It may contain copyright material
#  of the CCDC or of third parties, and may not be copied or further
#  disseminated in any form, whether machine-readable or not,
#  except for the purpose of generating routine backup copies
#  on your local computer system.
# 
#  For further information on the CCDC, data deposition and
#  data retrieval see:
#                         www.ccdc.cam.ac.uk
#
#  Bona fide researchers may freely download Mercury and enCIFer
#  from this site to visualise CIF-encoded structures and 
#  to carry out CIF format checking respectively.
#
data_3

#==========================================================================

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C20 H15 N2 O6 Zn'
_chemical_formula_sum            'C20 H15 N2 O6 Zn'
_chemical_formula_weight         444.73

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'

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                   10.791(2)
_cell_length_b                   17.717(3)
_cell_length_c                   9.7094(19)
_cell_angle_alpha                90.00
_cell_angle_beta                 92.49(3)
_cell_angle_gamma                90.00
_cell_volume                     1854.5(6)
_cell_formula_units_Z            4
_cell_measurement_temperature    223(2)
_cell_measurement_reflns_used    ?
_cell_measurement_theta_min      ?
_cell_measurement_theta_max      ?

_exptl_crystal_description       block
_exptl_crystal_colour            yellow
_exptl_crystal_size_max          0.30
_exptl_crystal_size_mid          0.25
_exptl_crystal_size_min          0.20
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.593
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             908
_exptl_absorpt_coefficient_mu    1.366
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.6747
_exptl_absorpt_correction_T_max  0.7618
_exptl_absorpt_process_details   'Sadabs, (Sheldrick 2001)'
_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      223(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         0
_diffrn_standards_interval_count 0
_diffrn_standards_interval_time  0
_diffrn_standards_decay_%        0
_diffrn_reflns_number            8181
_diffrn_reflns_av_R_equivalents  0.0434
_diffrn_reflns_av_sigmaI/netI    0.0423
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_k_min       -19
_diffrn_reflns_limit_k_max       21
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_limit_l_max       9
_diffrn_reflns_theta_min         1.89
_diffrn_reflns_theta_max         25.05
_reflns_number_total             3281
_reflns_number_gt                2798
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'Bruker SMART'
_computing_cell_refinement       'Bruker SMART'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXTL (Sheldrick, 2008)'
_computing_structure_refinement  SHELXTL
_computing_molecular_graphics    Diamond
_computing_publication_material  'SHELXTL and PLATON (Spek, 2009)'

_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)+(0.1089P)²+2.3404P] 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         3281
_refine_ls_number_parameters     258
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0646
_refine_ls_R_factor_gt           0.0570
_refine_ls_wR_factor_ref         0.1741
_refine_ls_wR_factor_gt          0.1657
_refine_ls_goodness_of_fit_ref   1.077
_refine_ls_restrained_S_all      1.077
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
Zn1 Zn 0.56874(5) 0.43271(3) -0.14915(4) 0.0305(2) Uani 1 1 d . . .
N1 N 0.4544(3) 0.34679(19) -0.1023(3) 0.0279(8) Uani 1 1 d . . .
N2 N 0.9512(3) 0.2597(2) 0.3149(3) 0.0324(8) Uani 1 1 d . . .
O1 O 0.6820(3) 0.43748(15) 0.0148(3) 0.0255(6) Uani 1 1 d . . .
O2 O 0.5358(3) 0.47360(17) 0.1561(3) 0.0327(7) Uani 1 1 d . . .
O3 O 0.6123(3) 0.44414(17) 0.6592(3) 0.0341(7) Uani 1 1 d . . .
O4 O 0.7184(3) 0.34417(17) 0.7309(3) 0.0346(6) Uani 1 1 d . . .
O5 O 0.9727(4) 0.21227(19) 0.4040(3) 0.0471(9) Uani 1 1 d . . .
O6 O 1.0071(3) 0.2648(2) 0.2086(3) 0.0459(9) Uani 1 1 d . . .
C1 C 0.4767(5) 0.2748(3) -0.1396(6) 0.0460(13) Uani 1 1 d . . .
H1 H 0.5476 0.2648 -0.1894 0.055 Uiso 1 1 calc R . .
C2 C 0.4014(5) 0.2158(3) -0.1086(6) 0.0463(13) Uani 1 1 d . . .
H2 H 0.4214 0.1665 -0.1359 0.056 Uiso 1 1 calc R . .
C3 C 0.2939(4) 0.2289(2) -0.0359(5) 0.0337(10) Uani 1 1 d . . .
C4 C 0.2734(4) 0.3027(2) 0.0056(5) 0.0320(10) Uani 1 1 d . . .
H4 H 0.2046 0.3141 0.0581 0.038 Uiso 1 1 calc R . .
C5 C 0.3539(4) 0.3594(2) -0.0302(4) 0.0317(9) Uani 1 1 d . . .
H5 H 0.3371 0.4091 -0.0026 0.038 Uiso 1 1 calc R . .
C6 C 0.2040(4) 0.1708(2) -0.0039(5) 0.0377(11) Uani 1 1 d . . .
H6 H 0.1391 0.1852 0.0519 0.045 Uiso 1 1 calc R . .
C7 C 0.2046(5) 0.0989(2) -0.0461(5) 0.0364(10) Uani 1 1 d . . .
H7 H 0.2728 0.0811 -0.0937 0.044 Uiso 1 1 calc R . .
C8 C 0.0868(5) 0.0240(3) -0.2775(5) 0.0441(12) Uani 1 1 d . . .
H8A H 0.0843 -0.0232 -0.3281 0.066 Uiso 1 1 calc R . .
H8B H 0.1713 0.0428 -0.2711 0.066 Uiso 1 1 calc R . .
H8C H 0.0339 0.0608 -0.3252 0.066 Uiso 1 1 calc R . .
C9 C 0.0416(4) 0.0112(2) -0.1345(4) 0.0301(9) Uani 1 1 d . . .
C10 C 0.1015(4) 0.0464(2) -0.0202(4) 0.0300(9) Uani 1 1 d . . .
C11 C 0.0611(4) 0.0345(2) 0.1149(4) 0.0297(9) Uani 1 1 d . . .
C12 C 0.1317(5) 0.0676(2) 0.2384(5) 0.0362(11) Uani 1 1 d . . .
H12A H 0.2157 0.0794 0.2139 0.054 Uiso 1 1 calc R . .
H12B H 0.1341 0.0313 0.3133 0.054 Uiso 1 1 calc R . .
H12C H 0.0908 0.1133 0.2674 0.054 Uiso 1 1 calc R . .
C13 C 0.7023(4) 0.4026(2) 0.2495(3) 0.0208(8) Uani 1 1 d . . .
C14 C 0.7978(4) 0.3523(2) 0.2255(3) 0.0223(8) Uani 1 1 d . . .
H14 H 0.8248 0.3443 0.1359 0.027 Uiso 1 1 calc R . .
C15 C 0.8518(4) 0.3145(2) 0.3371(4) 0.0242(8) Uani 1 1 d . . .
C16 C 0.8155(4) 0.3250(2) 0.4705(4) 0.0252(8) Uani 1 1 d . . .
H16 H 0.8529 0.2976 0.5439 0.030 Uiso 1 1 calc R . .
C17 C 0.7229(4) 0.3768(2) 0.4937(3) 0.0239(8) Uani 1 1 d . . .
C18 C 0.6665(4) 0.4154(2) 0.3845(4) 0.0218(8) Uani 1 1 d . . .
H18 H 0.6036 0.4506 0.4008 0.026 Uiso 1 1 calc R . .
C19 C 0.6352(4) 0.4419(2) 0.1320(4) 0.0221(8) Uani 1 1 d . . .
C20 C 0.6842(5) 0.3884(3) 0.6390(4) 0.0346(6) Uani 1 1 d . . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Zn1 O3 1.950(3) 1_554 ?
Zn1 O1 1.966(3) . ?
Zn1 O2 2.006(3) 3_665 ?
Zn1 N1 2.024(3) . ?
Zn1 O4 2.567(3) 1_554 ?
Zn1 C20 2.574(4) 1_554 ?
N1 C5 1.334(5) . ?
N1 C1 1.351(6) . ?
N2 O6 1.222(5) . ?
N2 O5 1.221(5) . ?
N2 C15 1.469(5) . ?
O1 C19 1.267(5) . ?
O2 C19 1.242(5) . ?
O2 Zn1 2.006(3) 3_665 ?
O3 C20 1.277(5) . ?
O3 Zn1 1.950(3) 1_556 ?
O4 C20 1.232(5) . ?
O4 Zn1 2.567(3) 1_556 ?
C1 C2 1.366(7) . ?
C1 H1 0.9400 . ?
C2 C3 1.403(6) . ?
C2 H2 0.9400 . ?
C3 C4 1.388(6) . ?
C3 C6 1.458(6) . ?
C4 C5 1.383(6) . ?
C4 H4 0.9400 . ?
C5 H5 0.9400 . ?
C6 C7 1.338(6) . ?
C6 H6 0.9400 . ?
C7 C10 1.480(6) . ?
C7 H7 0.9400 . ?
C8 C9 1.509(6) . ?
C8 H8A 0.9700 . ?
C8 H8B 0.9700 . ?
C8 H8C 0.9700 . ?
C9 C11 1.392(6) 3 ?
C9 C10 1.405(6) . ?
C10 C11 1.416(6) . ?
C11 C9 1.392(6) 3 ?
C11 C12 1.511(6) . ?
C12 H12A 0.9700 . ?
C12 H12B 0.9700 . ?
C12 H12C 0.9700 . ?
C13 C14 1.389(5) . ?
C13 C18 1.401(5) . ?
C13 C19 1.496(5) . ?
C14 C15 1.382(5) . ?
C14 H14 0.9400 . ?
C15 C16 1.382(5) . ?
C16 C17 1.381(6) . ?
C16 H16 0.9400 . ?
C17 C18 1.381(5) . ?
C17 C20 1.502(5) . ?
C18 H18 0.9400 . ?
C20 Zn1 2.574(4) 1_556 ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
O3 Zn1 O1 126.98(13) 1_554 . ?
O3 Zn1 O2 92.31(12) 1_554 3_665 ?
O1 Zn1 O2 108.69(12) . 3_665 ?
O3 Zn1 N1 117.86(14) 1_554 . ?
O1 Zn1 N1 102.34(13) . . ?
O2 Zn1 N1 106.40(14) 3_665 . ?
O3 Zn1 O4 56.49(11) 1_554 1_554 ?
O1 Zn1 O4 90.72(11) . 1_554 ?
O2 Zn1 O4 148.66(10) 3_665 1_554 ?
N1 Zn1 O4 92.54(12) . 1_554 ?
O3 Zn1 C20 28.80(13) 1_554 1_554 ?
O1 Zn1 C20 110.79(14) . 1_554 ?
O2 Zn1 C20 121.10(13) 3_665 1_554 ?
N1 Zn1 C20 105.74(14) . 1_554 ?
O4 Zn1 C20 27.72(12) 1_554 1_554 ?
C5 N1 C1 117.2(4) . . ?
C5 N1 Zn1 120.6(3) . . ?
C1 N1 Zn1 122.2(3) . . ?
O6 N2 O5 124.3(4) . . ?
O6 N2 C15 117.8(3) . . ?
O5 N2 C15 117.9(3) . . ?
C19 O1 Zn1 118.2(3) . . ?
C19 O2 Zn1 148.9(3) . 3_665 ?
C20 O3 Zn1 103.9(2) . 1_556 ?
C20 O4 Zn1 76.4(2) . 1_556 ?
N1 C1 C2 123.3(4) . . ?
N1 C1 H1 118.3 . . ?
C2 C1 H1 118.3 . . ?
C1 C2 C3 119.7(4) . . ?
C1 C2 H2 120.1 . . ?
C3 C2 H2 120.1 . . ?
C4 C3 C2 116.7(4) . . ?
C4 C3 C6 119.2(4) . . ?
C2 C3 C6 124.2(4) . . ?
C5 C4 C3 120.0(4) . . ?
C5 C4 H4 120.0 . . ?
C3 C4 H4 120.0 . . ?
N1 C5 C4 122.9(4) . . ?
N1 C5 H5 118.5 . . ?
C4 C5 H5 118.5 . . ?
C7 C6 C3 126.6(4) . . ?
C7 C6 H6 116.7 . . ?
C3 C6 H6 116.7 . . ?
C6 C7 C10 122.2(4) . . ?
C6 C7 H7 118.9 . . ?
C10 C7 H7 118.9 . . ?
C9 C8 H8A 109.5 . . ?
C9 C8 H8B 109.5 . . ?
H8A C8 H8B 109.5 . . ?
C9 C8 H8C 109.5 . . ?
H8A C8 H8C 109.5 . . ?
H8B C8 H8C 109.5 . . ?
C11 C9 C10 119.4(4) 3 . ?
C11 C9 C8 120.3(4) 3 . ?
C10 C9 C8 120.2(4) . . ?
C9 C10 C11 121.1(4) . . ?
C9 C10 C7 117.9(4) . . ?
C11 C10 C7 121.0(4) . . ?
C9 C11 C10 119.5(4) 3 . ?
C9 C11 C12 119.6(4) 3 . ?
C10 C11 C12 120.8(4) . . ?
C11 C12 H12A 109.5 . . ?
C11 C12 H12B 109.5 . . ?
H12A C12 H12B 109.5 . . ?
C11 C12 H12C 109.5 . . ?
H12A C12 H12C 109.5 . . ?
H12B C12 H12C 109.5 . . ?
C14 C13 C18 119.9(3) . . ?
C14 C13 C19 120.5(3) . . ?
C18 C13 C19 119.6(3) . . ?
C15 C14 C13 118.0(3) . . ?
C15 C14 H14 121.0 . . ?
C13 C14 H14 121.0 . . ?
C16 C15 C14 122.8(4) . . ?
C16 C15 N2 117.8(3) . . ?
C14 C15 N2 119.4(3) . . ?
C17 C16 C15 118.6(3) . . ?
C17 C16 H16 120.7 . . ?
C15 C16 H16 120.7 . . ?
C16 C17 C18 120.1(3) . . ?
C16 C17 C20 118.4(3) . . ?
C18 C17 C20 121.5(4) . . ?
C17 C18 C13 120.5(3) . . ?
C17 C18 H18 119.7 . . ?
C13 C18 H18 119.7 . . ?
O2 C19 O1 125.3(4) . . ?
O2 C19 C13 117.4(3) . . ?
O1 C19 C13 117.2(3) . . ?
O4 C20 O3 123.1(3) . . ?
O4 C20 C17 120.4(4) . . ?
O3 C20 C17 116.4(4) . . ?
O4 C20 Zn1 75.8(2) . 1_556 ?
O3 C20 Zn1 47.35(18) . 1_556 ?
C17 C20 Zn1 162.9(3) . 1_556 ?

_diffrn_measured_fraction_theta_max 1.000
_diffrn_reflns_theta_full        25.05
_diffrn_measured_fraction_theta_full 1.000
_refine_diff_density_max         0.933
_refine_diff_density_min         -0.876
_refine_diff_density_rms         0.113
_database_code_depnum_ccdc_archive 'CCDC 977635'
#######################################################################
#
#                 Cambridge Crystallographic Data Centre
#                                CCDC 
# 
#######################################################################
# 
#  This CIF contains data from an original supplementary publication
#  deposited with the CCDC, and may include chemical, crystal,
#  experimental, refinement, atomic coordinates,
#  anisotropic displacement parameters and molecular geometry data,
#  as required by the journal to which it was submitted.
#
#  This CIF is provided on the understanding that it is used for bona
#  fide research purposes only. It may contain copyright material
#  of the CCDC or of third parties, and may not be copied or further
#  disseminated in any form, whether machine-readable or not,
#  except for the purpose of generating routine backup copies
#  on your local computer system.
# 
#  For further information on the CCDC, data deposition and
#  data retrieval see:
#                         www.ccdc.cam.ac.uk
#
#  Bona fide researchers may freely download Mercury and enCIFer
#  from this site to visualise CIF-encoded structures and 
#  to carry out CIF format checking respectively.
#
data_4

#==========================================================================

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C20 H17 N2 O4 Zn, 2(H2 O)'
_chemical_formula_sum            'C20 H21 N2 O6 Zn'
_chemical_formula_weight         450.78

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'

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                   16.096(3)
_cell_length_b                   7.6958(15)
_cell_length_c                   16.148(3)
_cell_angle_alpha                90.00
_cell_angle_beta                 99.06(3)
_cell_angle_gamma                90.00
_cell_volume                     1975.3(7)
_cell_formula_units_Z            4
_cell_measurement_temperature    223(2)
_cell_measurement_reflns_used    ?
_cell_measurement_theta_min      ?
_cell_measurement_theta_max      ?

_exptl_crystal_description       block
_exptl_crystal_colour            yellow
_exptl_crystal_size_max          0.30
_exptl_crystal_size_mid          0.25
_exptl_crystal_size_min          0.20
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.516
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             932
_exptl_absorpt_coefficient_mu    1.283
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.6995
_exptl_absorpt_correction_T_max  0.7834
_exptl_absorpt_process_details   'Sadabs, (Sheldrick 2001)'
_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      223(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         0
_diffrn_standards_interval_count 0
_diffrn_standards_interval_time  0
_diffrn_standards_decay_%        0
_diffrn_reflns_number            8602
_diffrn_reflns_av_R_equivalents  0.0461
_diffrn_reflns_av_sigmaI/netI    0.0423
_diffrn_reflns_limit_h_min       -19
_diffrn_reflns_limit_h_max       18
_diffrn_reflns_limit_k_min       -6
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_theta_min         2.55
_diffrn_reflns_theta_max         25.05
_reflns_number_total             3497
_reflns_number_gt                2751
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'Bruker SMART'
_computing_cell_refinement       'Bruker SMART'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXTL (Sheldrick, 2008)'
_computing_structure_refinement  SHELXTL
_computing_molecular_graphics    Diamond
_computing_publication_material  'SHELXTL and PLATON (Spek, 2009)'

_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)+(0.1755P)²+1.8399P] 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         3497
_refine_ls_number_parameters     264
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0915
_refine_ls_R_factor_gt           0.0791
_refine_ls_wR_factor_ref         0.2498
_refine_ls_wR_factor_gt          0.2270
_refine_ls_goodness_of_fit_ref   1.038
_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
Zn1 Zn 0.36549(5) 0.50407(6) 0.21078(4) 0.0479(3) Uani 1 1 d . . .
N1 N 0.2662(3) 0.6572(5) 0.1632(2) 0.0437(10) Uani 1 1 d . . .
N2 N 0.4693(3) 0.8787(4) 0.6700(2) 0.0375(9) Uani 1 1 d . . .
H2A H 0.4984 0.9604 0.6456 0.045 Uiso 1 1 calc R . .
H2B H 0.5041 0.8349 0.7151 0.045 Uiso 1 1 calc R . .
O1 O 0.3724(3) 0.5343(4) 0.3312(2) 0.0442(9) Uani 1 1 d . . .
O2 O 0.4232(2) 0.8045(4) 0.34908(19) 0.0482(9) Uani 1 1 d . . .
O3 O 0.3504(3) 0.1527(4) 0.5687(2) 0.0573(11) Uani 1 1 d . . .
O4 O 0.3868(2) 0.2475(4) 0.69781(19) 0.0454(9) Uani 1 1 d . . .
C1 C 0.2464(4) 0.7946(7) 0.2083(3) 0.0593(15) Uani 1 1 d . . .
H1 H 0.2698 0.8000 0.2653 0.071 Uiso 1 1 calc R . .
C2 C 0.1943(4) 0.9266(8) 0.1756(4) 0.0617(16) Uani 1 1 d . . .
H2 H 0.1829 1.0192 0.2101 0.074 Uiso 1 1 calc R . .
C3 C 0.1587(4) 0.9239(7) 0.0931(4) 0.0585(15) Uani 1 1 d . . .
C4 C 0.1784(5) 0.7803(8) 0.0456(4) 0.0691(18) Uani 1 1 d . . .
H4 H 0.1558 0.7728 -0.0117 0.083 Uiso 1 1 calc R . .
C5 C 0.2301(4) 0.6524(7) 0.0823(3) 0.0582(15) Uani 1 1 d . . .
H5 H 0.2409 0.5565 0.0496 0.070 Uiso 1 1 calc R . .
C6 C 0.1073(4) 1.0640(9) 0.0518(4) 0.0698(18) Uani 1 1 d . . .
H6 H 0.0730 1.0374 0.0007 0.084 Uiso 1 1 calc R . .
C7 C 0.1044(5) 1.2261(8) 0.0795(4) 0.0714(18) Uani 1 1 d . . .
H7 H 0.1385 1.2530 0.1307 0.086 Uiso 1 1 calc R . .
C8 C 0.0047(9) 1.4181(13) 0.1750(5) 0.128(5) Uani 1 1 d . . .
H8A H -0.0084 1.5198 0.2060 0.191 Uiso 1 1 calc R . .
H8B H 0.0602 1.3758 0.1983 0.191 Uiso 1 1 calc R . .
H8C H -0.0367 1.3281 0.1792 0.191 Uiso 1 1 calc R . .
C9 C 0.0029(6) 1.4652(10) 0.0850(5) 0.080(2) Uani 1 1 d . . .
C10 C 0.0519(5) 1.3682(8) 0.0368(4) 0.0705(18) Uani 1 1 d . . .
C11 C 0.0518(6) 1.4082(9) -0.0481(4) 0.080(2) Uani 1 1 d . . .
C12 C 0.1104(8) 1.3184(13) -0.0984(6) 0.125(4) Uani 1 1 d . . .
H12A H 0.0809 1.2239 -0.1302 0.188 Uiso 1 1 calc R . .
H12B H 0.1583 1.2726 -0.0608 0.188 Uiso 1 1 calc R . .
H12C H 0.1297 1.4009 -0.1366 0.188 Uiso 1 1 calc R . .
C13 C 0.4081(3) 0.6358(5) 0.4704(3) 0.0347(10) Uani 1 1 d . . .
C14 C 0.3868(3) 0.4764(5) 0.5000(3) 0.0349(10) Uani 1 1 d . . .
H14 H 0.3667 0.3876 0.4621 0.042 Uiso 1 1 calc R . .
C15 C 0.3951(3) 0.4467(5) 0.5862(3) 0.0348(10) Uani 1 1 d . . .
C16 C 0.4227(3) 0.5788(5) 0.6418(3) 0.0357(10) Uani 1 1 d . . .
H16 H 0.4268 0.5605 0.6998 0.043 Uiso 1 1 calc R . .
C17 C 0.4446(3) 0.7410(5) 0.6109(2) 0.0342(10) Uani 1 1 d . . .
C18 C 0.4368(3) 0.7684(5) 0.5254(2) 0.0357(10) Uani 1 1 d . . .
H18 H 0.4510 0.8768 0.5047 0.043 Uiso 1 1 calc R . .
C19 C 0.4014(3) 0.6637(5) 0.3762(2) 0.0372(10) Uani 1 1 d . . .
C20 C 0.3753(3) 0.2709(5) 0.6188(3) 0.0393(11) Uani 1 1 d . . .
O5 O 0.3095(6) 0.0725(11) 0.3886(5) 0.138(3) Uani 1 1 d . . .
H1W H 0.3312 0.1081 0.4370 0.207 Uiso 1 1 d R . .
H2W H 0.3166 -0.0354 0.3810 0.207 Uiso 1 1 d R . .
O6 O 0.2305(7) 0.3244(12) 0.2771(7) 0.181(4) Uani 1 1 d . . .
H3W H 0.2751 0.2802 0.3041 0.272 Uiso 1 1 d R . .
H4W H 0.1989 0.4106 0.2828 0.272 Uiso 1 1 d R . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Zn1 O1 1.944(3) . ?
Zn1 O4 1.983(3) 4_565 ?
Zn1 N1 2.037(4) . ?
Zn1 N2 2.094(4) 4_575 ?
N1 C5 1.344(6) . ?
N1 C1 1.349(7) . ?
N2 C17 1.439(5) . ?
N2 Zn1 2.094(4) 4_576 ?
N2 H2A 0.9100 . ?
N2 H2B 0.9100 . ?
O1 C19 1.277(5) . ?
O2 C19 1.240(5) . ?
O3 C20 1.240(5) . ?
O4 C20 1.273(5) . ?
O4 Zn1 1.983(3) 4_566 ?
C1 C2 1.370(8) . ?
C1 H1 0.9400 . ?
C2 C3 1.366(8) . ?
C2 H2 0.9400 . ?
C3 C4 1.410(8) . ?
C3 C6 1.456(8) . ?
C4 C5 1.363(8) . ?
C4 H4 0.9400 . ?
C5 H5 0.9400 . ?
C6 C7 1.328(10) . ?
C6 H6 0.9400 . ?
C7 C10 1.484(8) . ?
C7 H7 0.9400 . ?
C8 C9 1.494(11) . ?
C8 H8A 0.9700 . ?
C8 H8B 0.9700 . ?
C8 H8C 0.9700 . ?
C9 C11 1.383(9) 3_585 ?
C9 C10 1.407(11) . ?
C10 C11 1.404(10) . ?
C11 C9 1.383(9) 3_585 ?
C11 C12 1.506(12) . ?
C12 H12A 0.9700 . ?
C12 H12B 0.9700 . ?
C12 H12C 0.9700 . ?
C13 C14 1.380(6) . ?
C13 C18 1.384(6) . ?
C13 C19 1.523(5) . ?
C14 C15 1.396(6) . ?
C14 H14 0.9400 . ?
C15 C16 1.383(6) . ?
C15 C20 1.504(6) . ?
C16 C17 1.410(6) . ?
C16 H16 0.9400 . ?
C17 C18 1.383(6) . ?
C18 H18 0.9400 . ?
O5 H1W 0.8501 . ?
O5 H2W 0.8500 . ?
O6 H3W 0.8499 . ?
O6 H4W 0.8501 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
O1 Zn1 O4 103.82(14) . 4_565 ?
O1 Zn1 N1 103.06(16) . . ?
O4 Zn1 N1 131.59(16) 4_565 . ?
O1 Zn1 N2 109.86(15) . 4_575 ?
O4 Zn1 N2 103.15(15) 4_565 4_575 ?
N1 Zn1 N2 104.47(16) . 4_575 ?
C5 N1 C1 116.3(4) . . ?
C5 N1 Zn1 123.0(4) . . ?
C1 N1 Zn1 119.2(3) . . ?
C17 N2 Zn1 112.0(3) . 4_576 ?
C17 N2 H2A 109.2 . . ?
Zn1 N2 H2A 109.2 4_576 . ?
C17 N2 H2B 109.2 . . ?
Zn1 N2 H2B 109.2 4_576 . ?
H2A N2 H2B 107.9 . . ?
C19 O1 Zn1 128.4(3) . . ?
C20 O4 Zn1 104.1(3) . 4_566 ?
N1 C1 C2 123.8(5) . . ?
N1 C1 H1 118.1 . . ?
C2 C1 H1 118.1 . . ?
C3 C2 C1 120.1(5) . . ?
C3 C2 H2 119.9 . . ?
C1 C2 H2 119.9 . . ?
C2 C3 C4 116.6(5) . . ?
C2 C3 C6 123.9(6) . . ?
C4 C3 C6 119.4(6) . . ?
C5 C4 C3 120.2(5) . . ?
C5 C4 H4 119.9 . . ?
C3 C4 H4 119.9 . . ?
N1 C5 C4 123.0(5) . . ?
N1 C5 H5 118.5 . . ?
C4 C5 H5 118.5 . . ?
C7 C6 C3 126.1(6) . . ?
C7 C6 H6 117.0 . . ?
C3 C6 H6 117.0 . . ?
C6 C7 C10 125.6(6) . . ?
C6 C7 H7 117.2 . . ?
C10 C7 H7 117.2 . . ?
C9 C8 H8A 109.5 . . ?
C9 C8 H8B 109.5 . . ?
H8A C8 H8B 109.5 . . ?
C9 C8 H8C 109.5 . . ?
H8A C8 H8C 109.5 . . ?
H8B C8 H8C 109.5 . . ?
C11 C9 C10 120.6(7) 3_585 . ?
C11 C9 C8 120.2(8) 3_585 . ?
C10 C9 C8 118.9(7) . . ?
C11 C10 C9 120.6(6) . . ?
C11 C10 C7 122.0(7) . . ?
C9 C10 C7 117.5(6) . . ?
C9 C11 C10 118.5(7) 3_585 . ?
C9 C11 C12 120.1(7) 3_585 . ?
C10 C11 C12 121.4(6) . . ?
C11 C12 H12A 109.5 . . ?
C11 C12 H12B 109.5 . . ?
H12A C12 H12B 109.5 . . ?
C11 C12 H12C 109.5 . . ?
H12A C12 H12C 109.5 . . ?
H12B C12 H12C 109.5 . . ?
C14 C13 C18 120.6(4) . . ?
C14 C13 C19 119.3(4) . . ?
C18 C13 C19 120.1(4) . . ?
C13 C14 C15 120.1(4) . . ?
C13 C14 H14 120.0 . . ?
C15 C14 H14 120.0 . . ?
C16 C15 C14 119.8(4) . . ?
C16 C15 C20 119.9(4) . . ?
C14 C15 C20 120.3(4) . . ?
C15 C16 C17 119.6(4) . . ?
C15 C16 H16 120.2 . . ?
C17 C16 H16 120.2 . . ?
C18 C17 C16 120.0(4) . . ?
C18 C17 N2 121.5(4) . . ?
C16 C17 N2 118.4(3) . . ?
C17 C18 C13 119.8(4) . . ?
C17 C18 H18 120.1 . . ?
C13 C18 H18 120.1 . . ?
O2 C19 O1 125.3(4) . . ?
O2 C19 C13 119.8(4) . . ?
O1 C19 C13 114.9(4) . . ?
O3 C20 O4 122.0(4) . . ?
O3 C20 C15 119.7(4) . . ?
O4 C20 C15 118.2(4) . . ?
H1W O5 H2W 113.7 . . ?
H3W O6 H4W 136.8 . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
N2 H2A O2 0.91 2.20 3.034(5) 152.0 3_676
N2 H2B O4 0.91 2.18 3.063(5) 164.5 2_656
O5 H1W O3 0.85 2.13 2.945(8) 161.0 .
O5 H2W O2 0.85 2.24 2.895(9) 134.2 1_545
O6 H3W O5 0.85 2.12 2.809(13) 138.2 .

_diffrn_measured_fraction_theta_max 0.996
_diffrn_reflns_theta_full        25.05
_diffrn_measured_fraction_theta_full 0.996
_refine_diff_density_max         0.664
_refine_diff_density_min         -0.783
_refine_diff_density_rms         0.147
_database_code_depnum_ccdc_archive 'CCDC 977636'
#######################################################################
#
#                 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_5

#==========================================================================

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C33 H28 N2 O7 Zn2'
_chemical_formula_sum            'C33 H28 N2 O7 Zn2'
_chemical_formula_weight         695.35

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'

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                   18.621(4)
_cell_length_b                   9.7191(19)
_cell_length_c                   17.267(4)
_cell_angle_alpha                90.00
_cell_angle_beta                 98.76(3)
_cell_angle_gamma                90.00
_cell_volume                     3088.5(12)
_cell_formula_units_Z            4
_cell_measurement_temperature    223(2)
_cell_measurement_reflns_used    ?
_cell_measurement_theta_min      ?
_cell_measurement_theta_max      ?

_exptl_crystal_description       blcok
_exptl_crystal_colour            yellow
_exptl_crystal_size_max          0.28
_exptl_crystal_size_mid          0.25
_exptl_crystal_size_min          0.22
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.495
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1424
_exptl_absorpt_coefficient_mu    1.604
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.6623
_exptl_absorpt_correction_T_max  0.7192
_exptl_absorpt_process_details   'Sadabs, (Sheldrick 2001)'
_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      223(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         0
_diffrn_standards_interval_count 0
_diffrn_standards_interval_time  0
_diffrn_standards_decay_%        0
_diffrn_reflns_number            14288
_diffrn_reflns_av_R_equivalents  0.0520
_diffrn_reflns_av_sigmaI/netI    0.0605
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_h_max       22
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_theta_min         2.21
_diffrn_reflns_theta_max         25.05
_reflns_number_total             5434
_reflns_number_gt                3716
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'Bruker SMART'
_computing_cell_refinement       'Bruker SMART'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXTL (Sheldrick, 2008)'
_computing_structure_refinement  SHELXTL
_computing_molecular_graphics    Diamond
_computing_publication_material  'SHELXTL and PLATON (Spek, 2009)'

_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)+(0.1688P)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         5434
_refine_ls_number_parameters     401
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1085
_refine_ls_R_factor_gt           0.0792
_refine_ls_wR_factor_ref         0.2447
_refine_ls_wR_factor_gt          0.2100
_refine_ls_goodness_of_fit_ref   0.991
_refine_ls_restrained_S_all      0.991
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
Zn1 Zn 0.51601(4) 0.41713(9) 0.15570(4) 0.0512(3) Uani 1 1 d . . .
Zn2 Zn 0.65928(5) 0.61251(10) 0.17833(4) 0.0562(3) Uani 1 1 d . . .
N1 N 0.4149(3) 0.4906(6) 0.1504(3) 0.0476(13) Uani 1 1 d . . .
N2 N -0.2572(3) 1.4765(7) 0.1746(3) 0.0546(14) Uani 1 1 d . . .
O1 O 0.5538(3) 0.4263(5) 0.2711(2) 0.0497(11) Uani 1 1 d . . .
O2 O 0.6398(3) 0.5893(6) 0.2868(2) 0.0558(12) Uani 1 1 d . . .
O3 O 0.7251(3) 0.7806(6) 0.5469(3) 0.0681(15) Uani 1 1 d . . .
O4 O 0.6787(3) 0.6988(5) 0.6494(2) 0.0585(12) Uani 1 1 d . . .
O5 O 0.5473(2) 0.2673(5) 0.6284(2) 0.0475(10) Uani 1 1 d . . .
O6 O 0.4913(2) 0.1916(6) 0.5139(2) 0.0542(12) Uani 1 1 d . . .
O7 O 0.5775(2) 0.5434(6) 0.1121(2) 0.0551(12) Uani 1 1 d . . .
H7A H 0.5669 0.5891 0.0699 0.083 Uiso 1 1 d R . .
C1 C 0.3642(4) 0.4867(10) 0.0868(4) 0.065(2) Uani 1 1 d . . .
H1 H 0.3734 0.4340 0.0438 0.078 Uiso 1 1 calc R . .
C2 C 0.3002(4) 0.5548(11) 0.0813(4) 0.076(3) Uani 1 1 d . . .
H2 H 0.2661 0.5472 0.0354 0.091 Uiso 1 1 calc R . .
C3 C 0.2846(5) 0.6344(11) 0.1416(5) 0.075(2) Uani 1 1 d . . .
C4 C 0.3388(5) 0.6464(11) 0.2074(5) 0.074(2) Uani 1 1 d . . .
H4 H 0.3322 0.7057 0.2487 0.089 Uiso 1 1 calc R . .
C5 C 0.4021(4) 0.5699(9) 0.2110(4) 0.064(2) Uani 1 1 d . . .
H5 H 0.4368 0.5734 0.2566 0.076 Uiso 1 1 calc R . .
C6 C 0.2186(5) 0.7197(13) 0.1425(5) 0.094(4) Uani 1 1 d . . .
H6 H 0.2174 0.7710 0.1884 0.113 Uiso 1 1 calc R . .
C7 C 0.1634(4) 0.7329(10) 0.0896(5) 0.069(2) Uani 1 1 d . . .
H7 H 0.1617 0.6803 0.0436 0.083 Uiso 1 1 calc R . .
C8 C 0.1012(4) 0.8268(9) 0.0962(4) 0.0611(19) Uani 1 1 d . . .
C9 C 0.1085(4) 0.9701(10) 0.0891(4) 0.0627(19) Uani 1 1 d . . .
C10 C 0.0517(5) 1.0577(10) 0.0981(5) 0.068(2) Uani 1 1 d . . .
C11 C -0.0128(4) 1.0015(9) 0.1150(5) 0.064(2) Uani 1 1 d . . .
C12 C -0.0210(4) 0.8609(10) 0.1233(5) 0.067(2) Uani 1 1 d . . .
C13 C 0.0354(4) 0.7691(10) 0.1121(5) 0.069(2) Uani 1 1 d . . .
C14 C -0.0775(5) 1.0902(10) 0.1225(5) 0.071(2) Uani 1 1 d . . .
H14 H -0.1224 1.0608 0.0951 0.085 Uiso 1 1 calc R . .
C15 C -0.0781(5) 1.2040(11) 0.1631(5) 0.074(2) Uani 1 1 d . . .
H15 H -0.0339 1.2320 0.1925 0.089 Uiso 1 1 calc R . .
C16 C -0.1425(4) 1.2929(10) 0.1668(5) 0.0636(19) Uani 1 1 d . . .
C17 C -0.2125(5) 1.2650(9) 0.1297(5) 0.068(2) Uani 1 1 d . . .
H17 H -0.2225 1.1837 0.1006 0.082 Uiso 1 1 calc R . .
C18 C -0.2673(4) 1.3588(9) 0.1362(4) 0.0602(18) Uani 1 1 d . . .
H18 H -0.3146 1.3373 0.1117 0.072 Uiso 1 1 calc R . .
C19 C -0.1892(4) 1.5021(9) 0.2104(5) 0.0622(18) Uani 1 1 d . . .
H19 H -0.1805 1.5847 0.2386 0.075 Uiso 1 1 calc R . .
C20 C -0.1325(4) 1.4160(9) 0.2081(5) 0.066(2) Uani 1 1 d . . .
H20 H -0.0861 1.4394 0.2344 0.080 Uiso 1 1 calc R . .
C21 C 0.1810(5) 1.0317(12) 0.0703(5) 0.080(3) Uani 1 1 d . . .
H21A H 0.1726 1.0755 0.0192 0.120 Uiso 1 1 calc R . .
H21B H 0.2165 0.9588 0.0702 0.120 Uiso 1 1 calc R . .
H21C H 0.1990 1.0994 0.1098 0.120 Uiso 1 1 calc R . .
C22 C 0.0606(5) 1.2129(10) 0.0865(5) 0.078(2) Uani 1 1 d . . .
H22A H 0.0135 1.2536 0.0684 0.117 Uiso 1 1 calc R . .
H22B H 0.0925 1.2285 0.0479 0.117 Uiso 1 1 calc R . .
H22C H 0.0814 1.2546 0.1359 0.117 Uiso 1 1 calc R . .
C23 C -0.0906(5) 0.8004(11) 0.1454(7) 0.088(3) Uani 1 1 d . . .
H23A H -0.1203 0.8738 0.1617 0.131 Uiso 1 1 calc R . .
H23B H -0.0785 0.7356 0.1881 0.131 Uiso 1 1 calc R . .
H23C H -0.1173 0.7533 0.1005 0.131 Uiso 1 1 calc R . .
C24 C 0.0271(5) 0.6175(11) 0.1158(6) 0.083(3) Uani 1 1 d . . .
H24A H 0.0704 0.5734 0.1026 0.125 Uiso 1 1 calc R . .
H24B H -0.0148 0.5890 0.0789 0.125 Uiso 1 1 calc R . .
H24C H 0.0204 0.5910 0.1684 0.125 Uiso 1 1 calc R . .
C25 C 0.6026(3) 0.4919(7) 0.3998(3) 0.0392(13) Uani 1 1 d . . .
C26 C 0.6458(3) 0.5895(6) 0.4470(3) 0.0406(13) Uani 1 1 d . . .
H26 H 0.6717 0.6575 0.4241 0.049 Uiso 1 1 calc R . .
C27 C 0.6490(3) 0.5825(6) 0.5287(3) 0.0410(13) Uani 1 1 d . . .
C28 C 0.6135(3) 0.4810(7) 0.5613(3) 0.0386(13) Uani 1 1 d . . .
H28 H 0.6169 0.4768 0.6161 0.046 Uiso 1 1 calc R . .
C29 C 0.5721(3) 0.3825(7) 0.5154(3) 0.0393(13) Uani 1 1 d . . .
C30 C 0.5664(3) 0.3911(6) 0.4338(3) 0.0382(13) Uani 1 1 d . . .
H30 H 0.5375 0.3273 0.4021 0.046 Uiso 1 1 calc R . .
C31 C 0.5984(3) 0.5053(7) 0.3118(3) 0.0418(14) Uani 1 1 d . . .
C32 C 0.6898(4) 0.6969(7) 0.5768(3) 0.0497(15) Uani 1 1 d . . .
C33 C 0.5333(3) 0.2732(7) 0.5530(3) 0.0436(14) Uani 1 1 d . . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Zn1 O7 1.910(5) . ?
Zn1 O5 1.965(5) 4_565 ?
Zn1 N1 2.003(5) . ?
Zn1 O1 2.011(4) . ?
Zn2 O7 1.884(4) . ?
Zn2 O4 1.949(5) 4_575 ?
Zn2 O2 1.975(4) . ?
Zn2 N2 2.049(6) 1_645 ?
N1 C1 1.335(8) . ?
N1 C5 1.351(9) . ?
N2 C18 1.322(10) . ?
N2 C19 1.346(10) . ?
N2 Zn2 2.049(6) 1_465 ?
O1 C31 1.264(8) . ?
O2 C31 1.244(8) . ?
O3 C32 1.210(9) . ?
O4 C32 1.300(8) . ?
O4 Zn2 1.949(5) 4_576 ?
O5 C33 1.289(7) . ?
O5 Zn1 1.965(5) 4_566 ?
O6 C33 1.239(7) . ?
O7 H7A 0.8499 . ?
C1 C2 1.354(11) . ?
C1 H1 0.9400 . ?
C2 C3 1.362(12) . ?
C2 H2 0.9400 . ?
C3 C4 1.405(11) . ?
C3 C6 1.485(12) . ?
C4 C5 1.386(11) . ?
C4 H4 0.9400 . ?
C5 H5 0.9400 . ?
C6 C7 1.274(11) . ?
C6 H6 0.9400 . ?
C7 C8 1.492(11) . ?
C7 H7 0.9400 . ?
C8 C9 1.406(13) . ?
C8 C13 1.413(12) . ?
C9 C10 1.385(12) . ?
C9 C21 1.555(12) . ?
C10 C11 1.390(12) . ?
C10 C22 1.534(13) . ?
C11 C12 1.385(13) . ?
C11 C14 1.503(11) . ?
C12 C13 1.412(12) . ?
C12 C23 1.525(12) . ?
C13 C24 1.484(13) . ?
C14 C15 1.310(13) . ?
C14 H14 0.9400 . ?
C15 C16 1.487(12) . ?
C15 H15 0.9400 . ?
C16 C17 1.388(12) . ?
C16 C20 1.390(12) . ?
C17 C18 1.386(11) . ?
C17 H17 0.9400 . ?
C18 H18 0.9400 . ?
C19 C20 1.353(12) . ?
C19 H19 0.9400 . ?
C20 H20 0.9400 . ?
C21 H21A 0.9700 . ?
C21 H21B 0.9700 . ?
C21 H21C 0.9700 . ?
C22 H22A 0.9700 . ?
C22 H22B 0.9700 . ?
C22 H22C 0.9700 . ?
C23 H23A 0.9700 . ?
C23 H23B 0.9700 . ?
C23 H23C 0.9700 . ?
C24 H24A 0.9700 . ?
C24 H24B 0.9700 . ?
C24 H24C 0.9700 . ?
C25 C30 1.371(9) . ?
C25 C26 1.419(8) . ?
C25 C31 1.514(7) . ?
C26 C27 1.404(8) . ?
C26 H26 0.9400 . ?
C27 C28 1.355(9) . ?
C27 C32 1.520(8) . ?
C28 C29 1.398(8) . ?
C28 H28 0.9400 . ?
C29 C30 1.399(7) . ?
C29 C33 1.489(9) . ?
C30 H30 0.9400 . ?

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
O7 Zn1 O5 105.9(2) . 4_565 ?
O7 Zn1 N1 111.6(2) . . ?
O5 Zn1 N1 128.7(2) 4_565 . ?
O7 Zn1 O1 102.84(19) . . ?
O5 Zn1 O1 101.93(18) 4_565 . ?
N1 Zn1 O1 102.36(19) . . ?
O7 Zn2 O4 110.1(2) . 4_575 ?
O7 Zn2 O2 106.7(2) . . ?
O4 Zn2 O2 114.8(2) 4_575 . ?
O7 Zn2 N2 107.3(2) . 1_645 ?
O4 Zn2 N2 115.3(2) 4_575 1_645 ?
O2 Zn2 N2 101.9(2) . 1_645 ?
C1 N1 C5 117.8(6) . . ?
C1 N1 Zn1 124.7(5) . . ?
C5 N1 Zn1 116.4(4) . . ?
C18 N2 C19 116.2(6) . . ?
C18 N2 Zn2 121.6(5) . 1_465 ?
C19 N2 Zn2 122.2(6) . 1_465 ?
C31 O1 Zn1 132.8(4) . . ?
C31 O2 Zn2 128.1(4) . . ?
C32 O4 Zn2 108.9(4) . 4_576 ?
C33 O5 Zn1 105.1(4) . 4_566 ?
Zn2 O7 Zn1 117.9(2) . . ?
Zn2 O7 H7A 113.2 . . ?
Zn1 O7 H7A 126.8 . . ?
N1 C1 C2 123.3(7) . . ?
N1 C1 H1 118.4 . . ?
C2 C1 H1 118.4 . . ?
C1 C2 C3 120.8(7) . . ?
C1 C2 H2 119.6 . . ?
C3 C2 H2 119.6 . . ?
C2 C3 C4 117.1(7) . . ?
C2 C3 C6 126.7(7) . . ?
C4 C3 C6 116.0(8) . . ?
C5 C4 C3 119.5(7) . . ?
C5 C4 H4 120.3 . . ?
C3 C4 H4 120.3 . . ?
N1 C5 C4 121.4(6) . . ?
N1 C5 H5 119.3 . . ?
C4 C5 H5 119.3 . . ?
C7 C6 C3 128.9(9) . . ?
C7 C6 H6 115.6 . . ?
C3 C6 H6 115.6 . . ?
C6 C7 C8 123.9(8) . . ?
C6 C7 H7 118.1 . . ?
C8 C7 H7 118.1 . . ?
C9 C8 C13 120.5(7) . . ?
C9 C8 C7 120.9(7) . . ?
C13 C8 C7 118.6(8) . . ?
C10 C9 C8 120.9(8) . . ?
C10 C9 C21 119.2(8) . . ?
C8 C9 C21 119.8(7) . . ?
C9 C10 C11 118.7(9) . . ?
C9 C10 C22 119.4(8) . . ?
C11 C10 C22 121.9(8) . . ?
C12 C11 C10 121.4(7) . . ?
C12 C11 C14 117.1(8) . . ?
C10 C11 C14 121.5(8) . . ?
C11 C12 C13 120.9(7) . . ?
C11 C12 C23 121.1(8) . . ?
C13 C12 C23 118.0(9) . . ?
C12 C13 C8 117.4(9) . . ?
C12 C13 C24 122.5(8) . . ?
C8 C13 C24 120.1(8) . . ?
C15 C14 C11 127.1(9) . . ?
C15 C14 H14 116.4 . . ?
C11 C14 H14 116.4 . . ?
C14 C15 C16 125.9(8) . . ?
C14 C15 H15 117.0 . . ?
C16 C15 H15 117.0 . . ?
C17 C16 C20 116.6(7) . . ?
C17 C16 C15 124.9(8) . . ?
C20 C16 C15 118.4(7) . . ?
C18 C17 C16 119.0(8) . . ?
C18 C17 H17 120.5 . . ?
C16 C17 H17 120.5 . . ?
N2 C18 C17 124.0(7) . . ?
N2 C18 H18 118.0 . . ?
C17 C18 H18 118.0 . . ?
N2 C19 C20 123.8(8) . . ?
N2 C19 H19 118.1 . . ?
C20 C19 H19 118.1 . . ?
C19 C20 C16 120.2(7) . . ?
C19 C20 H20 119.9 . . ?
C16 C20 H20 119.9 . . ?
C9 C21 H21A 109.5 . . ?
C9 C21 H21B 109.5 . . ?
H21A C21 H21B 109.5 . . ?
C9 C21 H21C 109.5 . . ?
H21A C21 H21C 109.5 . . ?
H21B C21 H21C 109.5 . . ?
C10 C22 H22A 109.5 . . ?
C10 C22 H22B 109.5 . . ?
H22A C22 H22B 109.5 . . ?
C10 C22 H22C 109.5 . . ?
H22A C22 H22C 109.5 . . ?
H22B C22 H22C 109.5 . . ?
C12 C23 H23A 109.5 . . ?
C12 C23 H23B 109.5 . . ?
H23A C23 H23B 109.5 . . ?
C12 C23 H23C 109.5 . . ?
H23A C23 H23C 109.5 . . ?
H23B C23 H23C 109.5 . . ?
C13 C24 H24A 109.5 . . ?
C13 C24 H24B 109.5 . . ?
H24A C24 H24B 109.5 . . ?
C13 C24 H24C 109.5 . . ?
H24A C24 H24C 109.5 . . ?
H24B C24 H24C 109.5 . . ?
C30 C25 C26 120.2(5) . . ?
C30 C25 C31 122.5(5) . . ?
C26 C25 C31 117.2(6) . . ?
C27 C26 C25 118.6(6) . . ?
C27 C26 H26 120.7 . . ?
C25 C26 H26 120.7 . . ?
C28 C27 C26 120.2(5) . . ?
C28 C27 C32 122.6(5) . . ?
C26 C27 C32 117.1(6) . . ?
C27 C28 C29 121.7(5) . . ?
C27 C28 H28 119.2 . . ?
C29 C28 H28 119.2 . . ?
C28 C29 C30 118.7(6) . . ?
C28 C29 C33 120.3(5) . . ?
C30 C29 C33 121.0(5) . . ?
C25 C30 C29 120.5(5) . . ?
C25 C30 H30 119.7 . . ?
C29 C30 H30 119.7 . . ?
O2 C31 O1 126.6(5) . . ?
O2 C31 C25 117.6(5) . . ?
O1 C31 C25 115.8(6) . . ?
O3 C32 O4 125.3(6) . . ?
O3 C32 C27 121.1(5) . . ?
O4 C32 C27 113.5(6) . . ?
O6 C33 O5 122.4(6) . . ?
O6 C33 C29 121.8(5) . . ?
O5 C33 C29 115.8(5) . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
O7 H7A O6 0.85 1.94 2.756(6) 159.3 2_655

_diffrn_measured_fraction_theta_max 0.992
_diffrn_reflns_theta_full        25.05
_diffrn_measured_fraction_theta_full 0.992
_refine_diff_density_max         1.041
_refine_diff_density_min         -0.734
_refine_diff_density_rms         0.139

#===END
_database_code_depnum_ccdc_archive 'CCDC 977637'
