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

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#
#                 Cambridge Crystallographic Data Centre
#                                CCDC 
# 
#######################################################################
# 
#  This CIF contains data from an original supplementary publication
#  deposited with the CCDC, and may include chemical, crystal,
#  experimental, refinement, atomic coordinates,
#  anisotropic displacement parameters and molecular geometry data,
#  as required by the journal to which it was submitted.
#
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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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data_1

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C20 H11 N O8.50 Zn'
_chemical_formula_weight         466.67

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Zn Zn 0.2839 1.4301 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_symmetry_cell_setting           Monoclinic
_symmetry_space_group_name_H-M   'C2/c  '

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

_cell_length_a                   25.951(3)
_cell_length_b                   11.8662(14)
_cell_length_c                   20.436(4)
_cell_angle_alpha                90.00
_cell_angle_beta                 125.847(6)
_cell_angle_gamma                90.00
_cell_volume                     5101.1(13)
_cell_formula_units_Z            8
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    ?
_cell_measurement_theta_min      ?
_cell_measurement_theta_max      ?

_exptl_crystal_description       block
_exptl_crystal_colour            colorless
_exptl_crystal_size_max          0.25
_exptl_crystal_size_mid          0.22
_exptl_crystal_size_min          0.2
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.215
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1888
_exptl_absorpt_coefficient_mu    1.003
_exptl_absorpt_correction_type   ?
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   ?

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      296(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         '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         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            23575
_diffrn_reflns_av_R_equivalents  0.0773
_diffrn_reflns_av_sigmaI/netI    0.0613
_diffrn_reflns_limit_h_min       -30
_diffrn_reflns_limit_h_max       30
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_l_min       -23
_diffrn_reflns_limit_l_max       24
_diffrn_reflns_theta_min         1.94
_diffrn_reflns_theta_max         25.00
_reflns_number_total             4481
_reflns_number_gt                2786
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'Bruker SMART'
_computing_cell_refinement       'Bruker SMART'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'Bruker SHELXTL'
_computing_structure_refinement  'Bruker SHELXTL'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'

_refine_special_details          
; 
 Refinement of F² against ALL reflections.  The weighted R-factor wR and 
 goodness of fit S are based on F², conventional R-factors R are based 
 on F, with F set to zero for negative F². The threshold expression of 
 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is 
 not relevant to the choice of reflections for refinement.  R-factors based 
 on F² are statistically about twice as large as those based on F, and R- 
 factors based on ALL data will be even larger. 
;

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.1969P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         4481
_refine_ls_number_parameters     281
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1258
_refine_ls_R_factor_gt           0.0775
_refine_ls_wR_factor_ref         0.2750
_refine_ls_wR_factor_gt          0.2419
_refine_ls_goodness_of_fit_ref   1.007
_refine_ls_restrained_S_all      1.007
_refine_ls_shift/su_max          0.082
_refine_ls_shift/su_mean         0.008

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 0.55645(3) 0.53414(6) -0.16306(4) 0.0527(4) Uani 1 1 d . . .
C3 C 0.6810(3) 0.4572(6) 0.0724(4) 0.0619(19) Uani 1 1 d . . .
O2 O 0.6376(2) 0.5295(4) -0.0580(3) 0.0636(13) Uani 1 1 d . . .
C1 C 0.7740(3) 0.5328(6) 0.1911(4) 0.0563(17) Uani 1 1 d . . .
C6 C 0.7671(3) 0.4576(6) 0.2380(4) 0.065(2) Uani 1 1 d . . .
N1 N 0.8166(3) 0.4747(5) 0.3190(3) 0.0612(15) Uani 1 1 d . . .
O4 O 0.9981(2) 0.8665(4) 0.3478(2) 0.0596(11) Uani 1 1 d . . .
O1 O 0.5821(3) 0.4030(7) -0.0472(3) 0.110(2) Uani 1 1 d . . .
C2 C 0.7303(3) 0.5310(5) 0.1076(4) 0.0549(16) Uani 1 1 d . . .
H2A H 0.7349 0.5802 0.0759 0.066 Uiso 1 1 calc R . .
O3 O 0.9199(2) 0.8559(4) 0.2152(3) 0.0728(14) Uani 1 1 d . . .
C11 C 0.9375(3) 0.6951(5) 0.3792(3) 0.0528(15) Uani 1 1 d . . .
H11A H 0.9734 0.7288 0.4238 0.063 Uiso 1 1 calc R . .
C9 C 0.8597(3) 0.6843(5) 0.2340(3) 0.0508(15) Uani 1 1 d . . .
H9A H 0.8433 0.7087 0.1820 0.061 Uiso 1 1 calc R . .
C8 C 0.8302(3) 0.5987(5) 0.2462(3) 0.0457(14) Uani 1 1 d . . .
C7 C 0.6297(3) 0.4619(6) -0.0168(4) 0.0629(18) Uani 1 1 d . . .
C15 C 0.8212(3) 0.4220(6) 0.3853(3) 0.0538(15) Uani 1 1 d . . .
C10 C 0.9142(3) 0.7339(5) 0.3005(3) 0.0469(14) Uani 1 1 d . . .
C13 C 0.8547(3) 0.5626(6) 0.3243(4) 0.0527(15) Uani 1 1 d . . .
C5 C 0.7185(4) 0.3774(7) 0.2025(4) 0.079(2) Uani 1 1 d . . .
H5A H 0.7150 0.3242 0.2332 0.095 Uiso 1 1 calc R . .
C12 C 0.9085(3) 0.6103(6) 0.3911(4) 0.0567(16) Uani 1 1 d . . .
H12A H 0.9245 0.5852 0.4428 0.068 Uiso 1 1 calc R . .
C16 C 0.7703(3) 0.4226(7) 0.3889(4) 0.0701(19) Uani 1 1 d . . .
H16A H 0.7328 0.4577 0.3481 0.084 Uiso 1 1 calc R . .
C14 C 0.9466(3) 0.8252(5) 0.2881(4) 0.0538(15) Uani 1 1 d . . .
C19 C 0.8784(4) 0.3183(7) 0.5082(4) 0.084(2) Uani 1 1 d . . .
H19A H 0.9156 0.2826 0.5491 0.101 Uiso 1 1 calc R . .
C20 C 0.8757(3) 0.3701(6) 0.4441(4) 0.0670(19) Uani 1 1 d . . .
H20A H 0.9107 0.3686 0.4423 0.080 Uiso 1 1 calc R . .
C17 C 0.7737(4) 0.3722(7) 0.4517(4) 0.073(2) Uani 1 1 d . . .
H17A H 0.7388 0.3742 0.4537 0.087 Uiso 1 1 calc R . .
C18 C 0.8277(4) 0.3197(7) 0.5109(5) 0.079(2) Uani 1 1 d . . .
H18A H 0.8298 0.2848 0.5531 0.095 Uiso 1 1 calc R . .
C4 C 0.6764(4) 0.3811(7) 0.1206(4) 0.080(2) Uani 1 1 d . . .
H4A H 0.6427 0.3303 0.0956 0.096 Uiso 1 1 calc R . .
O1W O 0.5000 0.4321(6) -0.2500 0.085(2) Uani 1 2 d S . .
O2W O 0.4325(11) 0.3707(15) -0.117(2) 0.44(2) Uani 1 1 d . . .
O4W O 0.3506(11) 0.339(2) -0.2148(15) 0.425(17) Uani 1 1 d . . .
O5W O 0.4586(11) 0.236(6) -0.1453(15) 0.80(5) Uani 1 1 d . . .
O3W O 0.7140(18) 0.249(4) -0.0403(15) 0.57(3) Uani 1 1 d . . .
O6W O 0.5000 -0.006(5) -0.2500 0.38(3) Uani 0.66 2 d SP . .


_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 O1W 1.929(4) . ?
Zn1 O2 1.937(5) . ?
Zn1 O3 1.994(4) 7_665 ?
Zn1 O4 2.031(4) 8_465 ?
Zn1 C7 2.574(7) . ?
Zn1 Zn1 3.0028(14) 2_654 ?
C3 C2 1.358(9) . ?
C3 C4 1.393(9) . ?
C3 C7 1.502(9) . ?
O2 C7 1.262(8) . ?
C1 C2 1.389(9) . ?
C1 C6 1.396(9) . ?
C1 C8 1.443(9) . ?
C6 N1 1.393(9) . ?
C6 C5 1.397(10) . ?
N1 C13 1.397(8) . ?
N1 C15 1.432(7) . ?
O4 C14 1.266(7) . ?
O4 Zn1 2.031(4) 8_566 ?
O1 C7 1.226(8) . ?
C2 H2A 0.9300 . ?
O3 C14 1.276(7) . ?
O3 Zn1 1.994(4) 7_665 ?
C11 C12 1.361(9) . ?
C11 C10 1.425(8) . ?
C11 H11A 0.9300 . ?
C9 C8 1.379(8) . ?
C9 C10 1.394(8) . ?
C9 H9A 0.9300 . ?
C8 C13 1.395(8) . ?
C15 C20 1.355(9) . ?
C15 C16 1.364(9) . ?
C10 C14 1.480(9) . ?
C13 C12 1.379(9) . ?
C5 C4 1.362(10) . ?
C5 H5A 0.9300 . ?
C12 H12A 0.9300 . ?
C16 C17 1.373(9) . ?
C16 H16A 0.9300 . ?
C19 C18 1.350(11) . ?
C19 C20 1.410(9) . ?
C19 H19A 0.9300 . ?
C20 H20A 0.9300 . ?
C17 C18 1.352(11) . ?
C17 H17A 0.9300 . ?
C18 H18A 0.9300 . ?
C4 H4A 0.9300 . ?
O1W Zn1 1.929(4) 2_654 ?
O3W O3W 1.61(6) 7_655 ?

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
O1W Zn1 O2 138.5(2) . . ?
O1W Zn1 O3 102.94(18) . 7_665 ?
O2 Zn1 O3 97.81(19) . 7_665 ?
O1W Zn1 O4 104.63(16) . 8_465 ?
O2 Zn1 O4 106.95(19) . 8_465 ?
O3 Zn1 O4 99.2(2) 7_665 8_465 ?
O1W Zn1 C7 120.4(2) . . ?
O2 Zn1 C7 28.3(2) . . ?
O3 Zn1 C7 126.1(2) 7_665 . ?
O4 Zn1 C7 99.1(2) 8_465 . ?
O1W Zn1 Zn1 38.88(16) . 2_654 ?
O2 Zn1 Zn1 170.29(16) . 2_654 ?
O3 Zn1 Zn1 76.12(13) 7_665 2_654 ?
O4 Zn1 Zn1 81.73(12) 8_465 2_654 ?
C7 Zn1 Zn1 156.83(16) . 2_654 ?
C2 C3 C4 119.2(6) . . ?
C2 C3 C7 120.7(6) . . ?
C4 C3 C7 120.0(6) . . ?
C7 O2 Zn1 105.1(4) . . ?
C2 C1 C6 119.5(6) . . ?
C2 C1 C8 133.7(5) . . ?
C6 C1 C8 106.8(5) . . ?
N1 C6 C5 129.9(6) . . ?
N1 C6 C1 108.8(6) . . ?
C5 C6 C1 121.2(6) . . ?
C6 N1 C13 108.6(5) . . ?
C6 N1 C15 124.6(5) . . ?
C13 N1 C15 126.2(5) . . ?
C14 O4 Zn1 123.6(4) . 8_566 ?
C3 C2 C1 119.9(6) . . ?
C3 C2 H2A 120.0 . . ?
C1 C2 H2A 120.0 . . ?
C14 O3 Zn1 133.2(4) . 7_665 ?
C12 C11 C10 121.9(6) . . ?
C12 C11 H11A 119.1 . . ?
C10 C11 H11A 119.1 . . ?
C8 C9 C10 119.4(5) . . ?
C8 C9 H9A 120.3 . . ?
C10 C9 H9A 120.3 . . ?
C9 C8 C13 120.2(5) . . ?
C9 C8 C1 132.3(5) . . ?
C13 C8 C1 107.5(5) . . ?
O1 C7 O2 122.3(6) . . ?
O1 C7 C3 120.4(6) . . ?
O2 C7 C3 117.3(6) . . ?
O1 C7 Zn1 76.3(4) . . ?
O2 C7 Zn1 46.6(3) . . ?
C3 C7 Zn1 161.5(5) . . ?
C20 C15 C16 119.7(6) . . ?
C20 C15 N1 120.2(6) . . ?
C16 C15 N1 120.1(6) . . ?
C9 C10 C11 118.7(5) . . ?
C9 C10 C14 119.8(5) . . ?
C11 C10 C14 121.5(5) . . ?
C12 C13 N1 130.0(6) . . ?
C12 C13 C8 121.7(6) . . ?
N1 C13 C8 108.2(5) . . ?
C4 C5 C6 116.6(6) . . ?
C4 C5 H5A 121.7 . . ?
C6 C5 H5A 121.7 . . ?
C11 C12 C13 118.2(5) . . ?
C11 C12 H12A 120.9 . . ?
C13 C12 H12A 120.9 . . ?
C15 C16 C17 121.0(7) . . ?
C15 C16 H16A 119.5 . . ?
C17 C16 H16A 119.5 . . ?
O4 C14 O3 124.0(6) . . ?
O4 C14 C10 120.2(5) . . ?
O3 C14 C10 115.7(5) . . ?
C18 C19 C20 120.9(7) . . ?
C18 C19 H19A 119.6 . . ?
C20 C19 H19A 119.6 . . ?
C15 C20 C19 118.7(7) . . ?
C15 C20 H20A 120.6 . . ?
C19 C20 H20A 120.6 . . ?
C18 C17 C16 120.1(7) . . ?
C18 C17 H17A 119.9 . . ?
C16 C17 H17A 119.9 . . ?
C19 C18 C17 119.6(7) . . ?
C19 C18 H18A 120.2 . . ?
C17 C18 H18A 120.2 . . ?
C5 C4 C3 123.4(7) . . ?
C5 C4 H4A 118.3 . . ?
C3 C4 H4A 118.3 . . ?
Zn1 O1W Zn1 102.2(3) . 2_654 ?

_diffrn_measured_fraction_theta_max 0.999
_diffrn_reflns_theta_full        25.00
_diffrn_measured_fraction_theta_full 0.999
_refine_diff_density_max         1.173
_refine_diff_density_min         -1.128
_refine_diff_density_rms         0.207
_database_code_depnum_ccdc_archive 'CCDC 1009908'
