# 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.
#
#  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
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#  data retrieval see:
#                         www.ccdc.cam.ac.uk
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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_y
#TrackingRef '15198_web_deposit_cif_file_0_XinZhang_1352124953.CUP-1.cif'


_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C12 H11 N O9 Zn2'
_chemical_formula_weight         443.96

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           ?
_symmetry_space_group_name_H-M   ?

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

_cell_length_a                   10.3349(4)
_cell_length_b                   11.8962(4)
_cell_length_c                   20.2894(8)
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_volume                     2494.50(16)
_cell_formula_units_Z            4
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    ?
_cell_measurement_theta_min      ?
_cell_measurement_theta_max      ?

_exptl_crystal_description       ?
_exptl_crystal_colour            ?
_exptl_crystal_size_max          ?
_exptl_crystal_size_mid          ?
_exptl_crystal_size_min          ?
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.182
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             888
_exptl_absorpt_coefficient_mu    1.953
_exptl_absorpt_correction_type   ?
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   ?

_exptl_special_details           
;
?
;

_diffrn_ambient_temperature      293(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  ?
_diffrn_measurement_method       ?
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            18531
_diffrn_reflns_av_R_equivalents  0.0420
_diffrn_reflns_av_sigmaI/netI    0.0523
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_l_min       -26
_diffrn_reflns_limit_l_max       27
_diffrn_reflns_theta_min         1.98
_diffrn_reflns_theta_max         28.33
_reflns_number_total             6207
_reflns_number_gt                5062
_reflns_threshold_expression     >2sigma(I)

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

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

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.1279P)²+0.1367P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0.07(3)
_refine_ls_number_reflns         6207
_refine_ls_number_parameters     222
_refine_ls_number_restraints     6
_refine_ls_R_factor_all          0.0670
_refine_ls_R_factor_gt           0.0527
_refine_ls_wR_factor_ref         0.1908
_refine_ls_wR_factor_gt          0.1788
_refine_ls_goodness_of_fit_ref   1.080
_refine_ls_restrained_S_all      1.096
_refine_ls_shift/su_max          7.077
_refine_ls_shift/su_mean         0.198

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 0.14246(5) 0.67650(5) 0.99072(4) 0.02632(18) Uani 1 1 d . . .
Zn2 Zn 0.45562(5) 0.58325(5) 0.99026(3) 0.02614(18) Uani 1 1 d . . .
O3 O 0.1796(5) 0.5980(5) 0.9068(3) 0.0549(15) Uani 1 1 d . . .
O5 O 0.3848(5) 0.5430(5) 0.9036(2) 0.0512(14) Uani 1 1 d . . .
O6 O 0.5383(5) 0.4180(4) 0.9927(4) 0.0660(16) Uani 1 1 d . . .
O7 O 0.1220(5) 0.4547(5) 0.5765(2) 0.0563(15) Uani 1 1 d . . .
O8 O 0.3325(5) 0.4125(5) 0.5730(2) 0.0486(12) Uani 1 1 d . . .
O1 O 0.1192(3) 0.8380(3) 1.0078(2) 0.0321(9) Uani 1 1 d . . .
O2 O 0.3396(4) 0.7316(3) 0.9912(2) 0.0347(9) Uani 1 1 d . . .
O4 O -0.0413(4) 0.6247(4) 0.9754(3) 0.0491(13) Uani 1 1 d . . .
C6 C 0.2588(6) 0.5299(7) 0.8057(3) 0.0420(16) Uani 1 1 d . . .
C2 C 0.2423(7) 0.4735(6) 0.6724(3) 0.0427(16) Uani 1 1 d . . .
C7 C 0.1485(7) 0.5384(9) 0.7735(4) 0.060(2) Uani 1 1 d . . .
C5 C 0.3708(7) 0.4973(8) 0.7716(4) 0.061(2) Uani 1 1 d . . .
H5 H 0.4496 0.4948 0.7937 0.074 Uiso 1 1 calc R . .
C4 C 0.1379(7) 0.5082(9) 0.7090(4) 0.073(3) Uani 1 1 d . . .
H4 H 0.0570 0.5112 0.6889 0.087 Uiso 1 1 calc R . .
C3 C 0.3656(7) 0.4685(9) 0.7046(4) 0.070(3) Uani 1 1 d . . .
H3 H 0.4397 0.4470 0.6818 0.084 Uiso 1 1 calc R . .
C8 C 0.2783(6) 0.5586(7) 0.8779(3) 0.0416(16) Uani 1 1 d . . .
C9 C 0.3530(5) 0.8285(4) 1.0135(3) 0.0310(11) Uani 1 1 d . . .
C10 C 0.2299(6) 0.8934(5) 1.0314(4) 0.0378(15) Uani 1 1 d . . .
H10 H 0.234(7) 0.968(6) 1.011(4) 0.045 Uiso 1 1 calc . . .
C1 C 0.2325(6) 0.4439(6) 0.6025(3) 0.0369(14) Uani 1 1 d . . .
N1 N 0.0320(12) 0.5755(18) 0.8022(6) 0.190(8) Uani 1 1 d . . .
H1A H 0.0418 0.5802 0.8457 0.285 Uiso 1 1 calc R . .
H1B H -0.0309 0.5269 0.7929 0.285 Uiso 1 1 calc R . .
H1C H 0.0116 0.6428 0.7861 0.285 Uiso 1 1 calc R . .
C11 C 0.2240(8) 0.9068(10) 1.1068(5) 0.074(3) Uani 1 1 d . . .
H11A H 0.1393 0.9320 1.1194 0.110 Uiso 1 1 calc R . .
H11B H 0.2872 0.9609 1.1207 0.110 Uiso 1 1 calc R . .
H11C H 0.2417 0.8357 1.1274 0.110 Uiso 1 1 calc R . .
C12 C 0.5140(12) 0.3390(8) 1.0176(10) 0.138(7) Uani 1 1 d . . .
H12 H 0.4574 0.3482 1.0528 0.166 Uiso 1 1 calc R . .
O9 O 0.5480(15) 0.2350(8) 1.0079(10) 0.184(5) Uani 1 1 d U . .


_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 1.967(4) . ?
Zn1 O3 1.979(5) . ?
Zn1 O8 1.994(5) 2_565 ?
Zn1 O4 2.021(4) . ?
Zn1 O2 2.140(4) . ?
Zn2 O1 1.933(4) 3_567 ?
Zn2 O5 1.964(5) . ?
Zn2 O7 1.977(5) 2_565 ?
Zn2 O2 2.133(4) . ?
Zn2 O6 2.144(5) . ?
O3 C8 1.267(8) . ?
O5 C8 1.232(8) . ?
O6 C12 1.095(13) . ?
O7 C1 1.264(7) . ?
O7 Zn2 1.977(5) 2_564 ?
O8 C1 1.251(8) . ?
O8 Zn1 1.994(5) 2_564 ?
O1 C10 1.404(7) . ?
O1 Zn2 1.933(4) 3_467 ?
O2 C9 1.246(7) . ?
O4 C9 1.247(6) 3_467 ?
C6 C7 1.319(10) . ?
C6 C5 1.403(9) . ?
C6 C8 1.517(8) . ?
C2 C4 1.372(10) . ?
C2 C3 1.434(10) . ?
C2 C1 1.465(8) . ?
C7 C4 1.362(10) . ?
C7 N1 1.408(14) . ?
C5 C3 1.403(10) . ?
C5 H5 0.9300 . ?
C4 H4 0.9300 . ?
C3 H3 0.9300 . ?
C9 O4 1.247(6) 3_567 ?
C9 C10 1.532(8) . ?
C10 C11 1.539(11) . ?
C10 H10 1.21(8) . ?
N1 H1A 0.8900 . ?
N1 H1B 0.8900 . ?
N1 H1C 0.8900 . ?
C11 H11A 0.9600 . ?
C11 H11B 0.9600 . ?
C11 H11C 0.9600 . ?
C12 O9 1.301(15) . ?
C12 H12 0.9300 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
O1 Zn1 O3 129.5(2) . . ?
O1 Zn1 O8 112.8(2) . 2_565 ?
O3 Zn1 O8 116.4(2) . 2_565 ?
O1 Zn1 O4 102.15(16) . . ?
O3 Zn1 O4 84.6(2) . . ?
O8 Zn1 O4 95.1(2) 2_565 . ?
O1 Zn1 O2 79.42(15) . . ?
O3 Zn1 O2 87.93(19) . . ?
O8 Zn1 O2 92.00(19) 2_565 . ?
O4 Zn1 O2 171.4(2) . . ?
O1 Zn2 O5 117.5(2) 3_567 . ?
O1 Zn2 O7 116.6(2) 3_567 2_565 ?
O5 Zn2 O7 125.8(2) . 2_565 ?
O1 Zn2 O2 95.19(15) 3_567 . ?
O5 Zn2 O2 90.0(2) . . ?
O7 Zn2 O2 87.3(2) 2_565 . ?
O1 Zn2 O6 95.49(19) 3_567 . ?
O5 Zn2 O6 86.9(2) . . ?
O7 Zn2 O6 86.1(3) 2_565 . ?
O2 Zn2 O6 169.12(18) . . ?
C8 O3 Zn1 136.8(5) . . ?
C8 O5 Zn2 132.4(4) . . ?
C12 O6 Zn2 134.9(8) . . ?
C1 O7 Zn2 135.5(4) . 2_564 ?
C1 O8 Zn1 131.8(4) . 2_564 ?
C10 O1 Zn2 118.6(3) . 3_467 ?
C10 O1 Zn1 114.8(3) . . ?
Zn2 O1 Zn1 125.71(18) 3_467 . ?
C9 O2 Zn2 134.9(4) . . ?
C9 O2 Zn1 113.0(3) . . ?
Zn2 O2 Zn1 106.37(16) . . ?
C9 O4 Zn1 131.2(4) 3_467 . ?
C7 C6 C5 119.3(6) . . ?
C7 C6 C8 125.2(6) . . ?
C5 C6 C8 115.4(6) . . ?
C4 C2 C3 117.7(6) . . ?
C4 C2 C1 122.8(6) . . ?
C3 C2 C1 119.5(6) . . ?
C6 C7 C4 121.7(7) . . ?
C6 C7 N1 123.9(7) . . ?
C4 C7 N1 114.3(8) . . ?
C3 C5 C6 120.9(7) . . ?
C3 C5 H5 119.5 . . ?
C6 C5 H5 119.6 . . ?
C7 C4 C2 122.4(7) . . ?
C7 C4 H4 118.8 . . ?
C2 C4 H4 118.8 . . ?
C5 C3 C2 117.8(7) . . ?
C5 C3 H3 121.2 . . ?
C2 C3 H3 121.1 . . ?
O5 C8 O3 125.4(6) . . ?
O5 C8 C6 119.5(6) . . ?
O3 C8 C6 115.0(6) . . ?
O4 C9 O2 125.2(5) 3_567 . ?
O4 C9 C10 117.3(5) 3_567 . ?
O2 C9 C10 117.4(4) . . ?
O1 C10 C9 111.1(5) . . ?
O1 C10 C11 110.8(6) . . ?
C9 C10 C11 108.7(6) . . ?
O1 C10 H10 100(4) . . ?
C9 C10 H10 101(4) . . ?
C11 C10 H10 124(4) . . ?
O8 C1 O7 125.2(6) . . ?
O8 C1 C2 118.5(6) . . ?
O7 C1 C2 116.2(6) . . ?
C7 N1 H1A 109.3 . . ?
C7 N1 H1B 109.2 . . ?
H1A N1 H1B 109.5 . . ?
C7 N1 H1C 109.9 . . ?
H1A N1 H1C 109.5 . . ?
H1B N1 H1C 109.5 . . ?
C10 C11 H11A 109.4 . . ?
C10 C11 H11B 109.4 . . ?
H11A C11 H11B 109.5 . . ?
C10 C11 H11C 109.6 . . ?
H11A C11 H11C 109.5 . . ?
H11B C11 H11C 109.5 . . ?
O6 C12 O9 133.2(19) . . ?
O6 C12 H12 113.9 . . ?
O9 C12 H12 112.9 . . ?

_diffrn_measured_fraction_theta_max 0.999
_diffrn_reflns_theta_full        28.33
_diffrn_measured_fraction_theta_full 0.999
_refine_diff_density_max         1.139
_refine_diff_density_min         -0.751
_refine_diff_density_rms         0.210


_database_code_depnum_ccdc_archive 'CCDC 909362'
