# Electronic Supplementary Material (ESI) for Dalton Transactions.
# 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
#  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_1
#TrackingRef '1.CIF'


_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C15 H10 N O4 Zn'
_chemical_formula_weight         333.61

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                   16.752(5)
_cell_length_b                   20.392(6)
_cell_length_c                   10.355(3)
_cell_angle_alpha                90.00
_cell_angle_beta                 115.486(4)
_cell_angle_gamma                90.00
_cell_volume                     3193.2(16)
_cell_formula_units_Z            8
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    9781
_cell_measurement_theta_min      2.00
_cell_measurement_theta_max      24.99

_exptl_crystal_description       block
_exptl_crystal_colour            colorless
_exptl_crystal_size_max          0.28
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.18
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.388
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1352
_exptl_absorpt_coefficient_mu    1.550
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.696
_exptl_absorpt_correction_T_max  0.757
_exptl_absorpt_process_details   'SADABS (Sheldrick, 1996)'

_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  'Bruker APEX CCD area-detector'
_diffrn_measurement_method       'ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            9781
_diffrn_reflns_av_R_equivalents  0.0211
_diffrn_reflns_av_sigmaI/netI    0.0205
_diffrn_reflns_limit_h_min       -19
_diffrn_reflns_limit_h_max       19
_diffrn_reflns_limit_k_min       -20
_diffrn_reflns_limit_k_max       24
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_theta_min         2.00
_diffrn_reflns_theta_max         24.99
_reflns_number_total             2771
_reflns_number_gt                2437
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'SMART (Bruker, 1997)'
_computing_cell_refinement       'SAINT (Bruker, 1999)'
_computing_data_reduction        SAINT
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    'SHELXTL-PLUS (Sheldrick, 1990)'
_computing_publication_material  SHELXL-97

_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)+(0.1450P)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         2771
_refine_ls_number_parameters     196
_refine_ls_number_restraints     2
_refine_ls_R_factor_all          0.0557
_refine_ls_R_factor_gt           0.0506
_refine_ls_wR_factor_ref         0.1744
_refine_ls_wR_factor_gt          0.1658
_refine_ls_goodness_of_fit_ref   1.059
_refine_ls_restrained_S_all      1.060
_refine_ls_shift/su_max          0.007
_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 0.44551(2) 0.275546(17) 1.09208(4) 0.0195(3) Uani 1 1 d . . .
O2 O 0.52931(18) 0.34786(14) 1.0922(3) 0.0381(7) Uani 1 1 d . . .
C1 C 0.5889(2) 0.37038(18) 1.2069(4) 0.0307(8) Uani 1 1 d . . .
C2 C 0.6365(3) 0.4305(2) 1.1940(5) 0.0366(9) Uani 1 1 d . . .
C7 C 0.7109(4) 0.4523(3) 1.3054(6) 0.082(2) Uani 1 1 d . . .
H7A H 0.7319 0.4285 1.3903 0.098 Uiso 1 1 calc R . .
C6 C 0.7586(4) 0.5091(4) 1.3007(6) 0.089(3) Uani 1 1 d . . .
H6A H 0.8114 0.5198 1.3784 0.107 Uiso 1 1 calc R . .
C3 C 0.6027(5) 0.4718(4) 1.0822(9) 0.099(2) Uani 1 1 d . . .
H3A H 0.5485 0.4623 1.0062 0.119 Uiso 1 1 calc R . .
N1 N 0.3729(2) 0.26821(15) 0.8746(4) 0.0287(8) Uani 1 1 d . . .
C12 C 0.2520(4) 0.2233(2) 0.6738(5) 0.0475(13) Uani 1 1 d . . .
H12A H 0.2019 0.1970 0.6407 0.057 Uiso 1 1 calc R . .
C11 C 0.3017(4) 0.2314(2) 0.8182(5) 0.0492(14) Uani 1 1 d . . .
H11A H 0.2839 0.2094 0.8801 0.059 Uiso 1 1 calc R . .
C15 C 0.3935(4) 0.3010(4) 0.7828(5) 0.078(2) Uani 1 1 d . . .
H15A H 0.4414 0.3296 0.8188 0.093 Uiso 1 1 calc R . .
C14 C 0.3480(4) 0.2949(4) 0.6384(6) 0.087(3) Uani 1 1 d . . .
H14A H 0.3660 0.3190 0.5793 0.104 Uiso 1 1 calc R . .
C4 C 0.6480(5) 0.5287(4) 1.0790(8) 0.096(2) Uani 1 1 d . . .
H4A H 0.6214 0.5557 0.9993 0.116 Uiso 1 1 calc R . .
C13 C 0.2764(3) 0.2541(2) 0.5781(4) 0.0339(9) Uani 1 1 d . . .
C5 C 0.7266(3) 0.5481(3) 1.1811(5) 0.0515(12) Uani 1 1 d . . .
C8 C 0.7757(3) 0.6060(2) 1.1745(5) 0.0433(10) Uani 1 1 d D . .
C9 C 0.8471(3) 0.6280(2) 1.2840(4) 0.0424(11) Uani 1 1 d D . .
C10 C 0.8988(3) 0.68527(19) 1.2689(4) 0.0323(9) Uani 1 1 d . . .
O3 O 0.8778(2) 0.70682(16) 1.1462(3) 0.0408(7) Uani 1 1 d . . .
O4 O 0.9598(2) 0.70668(16) 1.3816(3) 0.0436(8) Uani 1 1 d . . .
O1 O 0.6118(2) 0.34623(14) 1.3303(3) 0.0383(7) Uani 1 1 d . . .
H2 H 0.862(3) 0.605(2) 1.375(3) 0.057 Uiso 1 1 d D . .
H1 H 0.748(3) 0.635(2) 1.095(4) 0.057 Uiso 1 1 d D . .

loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_23
_atom_site_aniso_U_13
_atom_site_aniso_U_12
Zn1 0.0201(3) 0.0191(3) 0.0160(3) 0.00007(12) 0.0047(2) -0.00092(13)
O2 0.0352(15) 0.0377(16) 0.0361(15) -0.0021(13) 0.0104(13) -0.0165(13)
C1 0.0294(19) 0.0256(19) 0.043(2) -0.0020(16) 0.0209(18) -0.0046(15)
C2 0.043(2) 0.029(2) 0.040(2) 0.0006(17) 0.0204(19) -0.0109(18)
C7 0.095(5) 0.098(5) 0.036(3) 0.000(3) 0.014(3) -0.073(4)
C6 0.091(5) 0.122(5) 0.034(3) -0.008(3) 0.006(3) -0.087(4)
C3 0.077(4) 0.102(6) 0.101(6) 0.005(5) 0.022(4) -0.026(4)
N1 0.0289(18) 0.0323(18) 0.0209(17) 0.0005(12) 0.0069(15) -0.0061(13)
C12 0.046(3) 0.064(3) 0.025(2) -0.0024(17) 0.008(2) -0.033(2)
C11 0.049(3) 0.071(3) 0.022(2) 0.0020(18) 0.010(2) -0.031(2)
C15 0.065(3) 0.130(5) 0.029(3) -0.005(3) 0.012(2) -0.066(4)
C14 0.071(4) 0.149(6) 0.024(3) 0.007(3) 0.006(3) -0.074(4)
C4 0.086(5) 0.090(5) 0.089(5) 0.023(4) 0.014(4) -0.010(4)
C13 0.030(2) 0.049(2) 0.020(2) -0.0004(18) 0.0088(16) -0.010(2)
C5 0.045(3) 0.056(3) 0.051(3) -0.019(2) 0.019(2) -0.026(2)
C8 0.046(2) 0.044(3) 0.038(2) -0.0055(19) 0.017(2) -0.017(2)
C9 0.048(2) 0.040(2) 0.035(2) 0.0020(18) 0.014(2) -0.022(2)
C10 0.034(2) 0.030(2) 0.036(2) 0.0010(17) 0.0169(18) -0.0071(17)
O3 0.0479(18) 0.0379(15) 0.0362(18) 0.0017(14) 0.0176(15) -0.0199(15)
O4 0.0420(17) 0.0368(16) 0.0425(19) 0.0017(15) 0.0093(15) -0.0202(15)
O1 0.0440(16) 0.0359(15) 0.0352(15) 0.0020(12) 0.0173(13) -0.0173(13)

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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Zn1 O3 2.028(3) 3_445 ?
Zn1 O2 2.036(3) . ?
Zn1 O4 2.048(3) 4_647 ?
Zn1 N1 2.053(4) . ?
Zn1 O1 2.076(3) 2_657 ?
Zn1 Zn1 2.9818(11) 2_657 ?
O2 C1 1.264(5) . ?
C1 O1 1.265(5) . ?
C1 C2 1.499(5) . ?
C2 C3 1.344(9) . ?
C2 C7 1.358(7) . ?
C7 C6 1.421(7) . ?
C6 C5 1.372(9) . ?
C3 C4 1.395(9) . ?
N1 C15 1.324(6) . ?
N1 C11 1.313(6) . ?
C12 C13 1.375(6) . ?
C12 C11 1.373(7) . ?
C15 C14 1.360(7) . ?
C14 C13 1.370(7) . ?
C4 C5 1.346(8) . ?
C13 C13 1.482(8) 7_556 ?
C5 C8 1.456(6) . ?
C8 C9 1.323(6) . ?
C9 C10 1.501(5) . ?
C10 O4 1.253(5) . ?
C10 O3 1.244(5) . ?
O3 Zn1 2.028(3) 3 ?
O4 Zn1 2.048(3) 4_657 ?
O1 Zn1 2.076(3) 2_657 ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
O3 Zn1 O2 165.49(13) 3_445 . ?
O3 Zn1 O4 89.02(15) 3_445 4_647 ?
O2 Zn1 O4 90.11(15) . 4_647 ?
O3 Zn1 N1 96.58(13) 3_445 . ?
O2 Zn1 N1 97.86(12) . . ?
O4 Zn1 N1 98.95(13) 4_647 . ?
O3 Zn1 O1 88.05(15) 3_445 2_657 ?
O2 Zn1 O1 86.01(13) . 2_657 ?
O4 Zn1 O1 152.36(13) 4_647 2_657 ?
N1 Zn1 O1 108.69(13) . 2_657 ?
O3 Zn1 Zn1 81.28(9) 3_445 2_657 ?
O2 Zn1 Zn1 84.41(8) . 2_657 ?
O4 Zn1 Zn1 77.31(9) 4_647 2_657 ?
N1 Zn1 Zn1 175.68(9) . 2_657 ?
O1 Zn1 Zn1 75.07(8) 2_657 2_657 ?
C1 O2 Zn1 122.0(2) . . ?
O2 C1 O1 125.5(3) . . ?
O2 C1 C2 116.6(4) . . ?
O1 C1 C2 117.8(4) . . ?
C3 C2 C7 114.8(5) . . ?
C3 C2 C1 123.1(5) . . ?
C7 C2 C1 121.4(4) . . ?
C2 C7 C6 124.2(5) . . ?
C5 C6 C7 119.8(5) . . ?
C2 C3 C4 120.6(7) . . ?
C15 N1 C11 115.9(4) . . ?
C15 N1 Zn1 122.4(3) . . ?
C11 N1 Zn1 121.7(3) . . ?
C13 C12 C11 120.1(4) . . ?
N1 C11 C12 124.2(4) . . ?
N1 C15 C14 123.2(5) . . ?
C15 C14 C13 121.5(5) . . ?
C5 C4 C3 125.8(7) . . ?
C12 C13 C14 115.0(4) . . ?
C12 C13 C13 120.8(5) . 7_556 ?
C14 C13 C13 124.1(5) . 7_556 ?
C6 C5 C4 114.2(5) . . ?
C6 C5 C8 120.2(5) . . ?
C4 C5 C8 125.6(5) . . ?
C9 C8 C5 123.7(4) . . ?
C8 C9 C10 121.6(4) . . ?
O4 C10 O3 126.0(4) . . ?
O4 C10 C9 116.7(3) . . ?
O3 C10 C9 117.3(4) . . ?
C10 O3 Zn1 125.5(3) . 3 ?
C10 O4 Zn1 129.6(3) . 4_657 ?
C1 O1 Zn1 132.2(3) . 2_657 ?

_diffrn_measured_fraction_theta_max 0.982
_diffrn_reflns_theta_full        24.99
_diffrn_measured_fraction_theta_full 0.982
_refine_diff_density_max         1.654
_refine_diff_density_min         -0.567
_refine_diff_density_rms         0.118


_database_code_depnum_ccdc_archive 'CCDC 899342'
