# Electronic Supplementary Material (ESI) for ChemComm.
# 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
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# 
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#  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

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
 ?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C10 H11 N4 O5 Zn'
_chemical_formula_sum            'C10 H11 N4 O5 Zn'
_chemical_formula_weight         332.60

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                   13.7620(8)
_cell_length_b                   9.563(5)
_cell_length_c                   9.883(5)
_cell_angle_alpha                90.00
_cell_angle_beta                 101.074(5)
_cell_angle_gamma                90.00
_cell_volume                     1276.4(9)
_cell_formula_units_Z            4
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    6929
_cell_measurement_theta_min      2.61
_cell_measurement_theta_max      26.12

_exptl_crystal_description       block
_exptl_crystal_colour            colorless
_exptl_crystal_size_max          0.21
_exptl_crystal_size_mid          0.18
_exptl_crystal_size_min          0.16
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.731
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             676
_exptl_absorpt_coefficient_mu    1.950
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.6749
_exptl_absorpt_correction_T_max  0.7355
_exptl_absorpt_process_details   'SADABS(Sheldrick, 1996)'

_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      293(2)
_diffrn_radiation_wavelength     0.71069
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            6929
_diffrn_reflns_av_R_equivalents  0.0330
_diffrn_reflns_av_sigmaI/netI    0.0408
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_h_max       17
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_theta_min         2.61
_diffrn_reflns_theta_max         26.12
_reflns_number_total             2536
_reflns_number_gt                2024
_reflns_threshold_expression     >2σ(I)

_computing_data_collection       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_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 > 2σ(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)+(0.0450P)²+0.7094P] 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         2536
_refine_ls_number_parameters     181
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0497
_refine_ls_R_factor_gt           0.0357
_refine_ls_wR_factor_ref         0.0935
_refine_ls_wR_factor_gt          0.0862
_refine_ls_goodness_of_fit_ref   1.066
_refine_ls_restrained_S_all      1.066
_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 0.59568(3) 0.06824(4) -0.09915(3) 0.02078(13) Uani 1 1 d . . .
N3 N 0.55861(19) 0.2103(3) -0.2486(3) 0.0244(6) Uani 1 1 d . . .
O1 O 0.72691(17) -0.0136(3) -0.0983(3) 0.0414(6) Uani 1 1 d . . .
O2 O 0.77134(19) 0.1938(3) -0.0163(3) 0.0468(7) Uani 1 1 d . . .
N1 N 0.55982(19) 0.3463(3) -0.4295(3) 0.0231(6) Uani 1 1 d . . .
C5 C 0.9337(3) -0.0631(4) 0.0692(4) 0.0351(8) Uani 1 1 d . . .
H5 H 0.8893 -0.1065 0.1157 0.042 Uiso 1 1 calc R . .
N2 N 0.49243(19) 0.3994(3) -0.3566(3) 0.0239(6) Uani 1 1 d . . .
C3 C 0.7912(3) 0.0739(4) -0.0529(3) 0.0316(8) Uani 1 1 d . . .
C6 C 1.0338(3) -0.0952(4) 0.1049(4) 0.0328(8) Uani 1 1 d . . .
C4 C 0.8985(2) 0.0325(4) -0.0347(3) 0.0287(8) Uani 1 1 d . . .
O4 O 1.1560(2) -0.1726(3) 0.2886(3) 0.0569(9) Uani 1 1 d . . .
H4 H 1.1692 -0.2279 0.3530 0.085 Uiso 1 1 calc R . .
O3 O 1.0088(2) -0.2747(4) 0.2611(4) 0.0742(11) Uani 1 1 d . . .
N4 N 0.7720(3) -0.4216(4) -0.0514(4) 0.0526(9) Uani 1 1 d . . .
C2 C 0.5969(2) 0.2333(3) -0.3619(3) 0.0261(7) Uani 1 1 d . . .
H2 H 0.6441 0.1761 -0.3895 0.031 Uiso 1 1 calc R . .
C9 C 0.7171(5) -0.4494(8) -0.1865(6) 0.101(2) Uani 1 1 d . . .
H9A H 0.7621 -0.4682 -0.2475 0.152 Uiso 1 1 calc R . .
H9B H 0.6772 -0.3696 -0.2193 0.152 Uiso 1 1 calc R . .
H9C H 0.6752 -0.5291 -0.1836 0.152 Uiso 1 1 calc R . .
O5 O 0.6391(3) -0.3860(6) 0.0411(5) 0.1124(16) Uani 1 1 d . . .
C1 C 0.4943(3) 0.3164(3) -0.2513(3) 0.0293(7) Uani 1 1 d . . .
H1 H 0.4552 0.3293 -0.1852 0.035 Uiso 1 1 calc R . .
C10 C 0.7280(5) -0.3929(6) 0.0507(6) 0.0720(15) Uani 1 1 d . . .
H10 H 0.7675 -0.3766 0.1367 0.086 Uiso 1 1 calc R . .
C7 C 1.0644(3) -0.1921(4) 0.2244(4) 0.0407(9) Uani 1 1 d . . .
C8 C 0.8781(4) -0.4310(7) -0.0360(7) 0.0901(19) Uani 1 1 d . . .
H8A H 0.8949 -0.4529 -0.1234 0.135 Uiso 1 1 calc R . .
H8B H 0.9026 -0.5031 0.0293 0.135 Uiso 1 1 calc R . .
H8C H 0.9074 -0.3431 -0.0035 0.135 Uiso 1 1 calc R . .

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 0.0191(2) 0.0224(2) 0.0217(2) 0.00072(15) 0.00603(14) -0.00047(15)
N3 0.0238(14) 0.0259(14) 0.0247(14) 0.0067(11) 0.0078(12) 0.0044(12)
O1 0.0191(12) 0.0407(15) 0.0632(18) 0.0013(13) 0.0052(12) -0.0004(11)
O2 0.0311(14) 0.0559(18) 0.0496(16) -0.0162(14) -0.0016(13) 0.0109(13)
N1 0.0239(14) 0.0241(14) 0.0233(13) 0.0010(11) 0.0098(12) 0.0032(11)
C5 0.0282(18) 0.043(2) 0.0355(19) 0.0035(17) 0.0106(16) -0.0018(16)
N2 0.0223(14) 0.0255(14) 0.0260(14) 0.0036(11) 0.0099(12) 0.0057(11)
C3 0.0246(18) 0.042(2) 0.0276(17) 0.0051(16) 0.0036(15) 0.0069(16)
C6 0.0233(17) 0.043(2) 0.0316(18) 0.0039(15) 0.0034(15) 0.0045(15)
C4 0.0187(16) 0.0342(19) 0.0328(18) 0.0002(14) 0.0039(14) 0.0005(14)
O4 0.0347(16) 0.078(2) 0.0526(18) 0.0316(16) -0.0049(14) -0.0057(15)
O3 0.0451(18) 0.088(2) 0.084(2) 0.050(2) -0.0010(17) -0.0142(18)
N4 0.044(2) 0.061(2) 0.056(2) -0.0114(19) 0.0171(19) -0.0030(18)
C2 0.0246(16) 0.0288(18) 0.0264(16) 0.0037(14) 0.0089(14) 0.0052(14)
C9 0.064(4) 0.167(7) 0.072(4) -0.026(4) 0.012(3) -0.004(4)
O5 0.071(3) 0.174(5) 0.109(3) 0.008(3) 0.058(3) 0.026(3)
C1 0.0311(18) 0.0302(18) 0.0298(17) 0.0027(14) 0.0143(15) 0.0044(15)
C10 0.080(4) 0.072(4) 0.069(3) 0.004(3) 0.028(3) 0.011(3)
C7 0.0268(19) 0.052(2) 0.043(2) 0.0059(19) 0.0051(17) 0.0055(18)
C8 0.047(3) 0.125(5) 0.099(5) -0.024(4) 0.016(3) -0.006(3)

_geom_special_details            
;
 All s.u.'s (except the s.u. in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell s.u.'s are taken
 into account individually in the estimation of s.u.'s in distances, angles
 and torsion angles; correlations between s.u.'s in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell s.u.'s is used for estimating s.u.'s 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(2) . ?
Zn1 N3 1.999(3) . ?
Zn1 N1 2.010(3) 4_566 ?
Zn1 N2 2.016(3) 2_644 ?
N3 C1 1.344(4) . ?
N3 C2 1.344(4) . ?
O1 C3 1.237(4) . ?
O2 C3 1.249(4) . ?
N1 C2 1.321(4) . ?
N1 N2 1.376(3) . ?
N1 Zn1 2.010(3) 4_565 ?
C5 C6 1.389(5) . ?
C5 C4 1.391(5) . ?
N2 C1 1.305(4) . ?
N2 Zn1 2.016(3) 2_654 ?
C3 C4 1.506(5) . ?
C6 C4 1.400(5) 3_755 ?
C6 C7 1.497(5) . ?
C4 C6 1.400(5) 3_755 ?
O4 C7 1.312(4) . ?
O3 C7 1.203(5) . ?
N4 C10 1.302(6) . ?
N4 C9 1.428(6) . ?
N4 C8 1.441(6) . ?
O5 C10 1.210(6) . ?

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 N3 112.17(11) . . ?
O1 Zn1 N1 122.05(11) . 4_566 ?
N3 Zn1 N1 105.74(11) . 4_566 ?
O1 Zn1 N2 101.28(11) . 2_644 ?
N3 Zn1 N2 109.05(11) . 2_644 ?
N1 Zn1 N2 105.82(10) 4_566 2_644 ?
C1 N3 C2 102.8(3) . . ?
C1 N3 Zn1 127.0(2) . . ?
C2 N3 Zn1 129.9(2) . . ?
C3 O1 Zn1 108.9(2) . . ?
C2 N1 N2 105.7(2) . . ?
C2 N1 Zn1 128.5(2) . 4_565 ?
N2 N1 Zn1 125.82(19) . 4_565 ?
C6 C5 C4 121.4(3) . . ?
C1 N2 N1 106.4(2) . . ?
C1 N2 Zn1 125.4(2) . 2_654 ?
N1 N2 Zn1 128.27(19) . 2_654 ?
O1 C3 O2 123.1(3) . . ?
O1 C3 C4 118.8(3) . . ?
O2 C3 C4 118.1(3) . . ?
C5 C6 C4 120.1(3) . 3_755 ?
C5 C6 C7 116.9(3) . . ?
C4 C6 C7 122.9(3) 3_755 . ?
C5 C4 C6 118.5(3) . 3_755 ?
C5 C4 C3 117.1(3) . . ?
C6 C4 C3 124.0(3) 3_755 . ?
C10 N4 C9 121.5(5) . . ?
C10 N4 C8 123.0(5) . . ?
C9 N4 C8 115.5(4) . . ?
N1 C2 N3 112.4(3) . . ?
N2 C1 N3 112.7(3) . . ?
O5 C10 N4 124.4(6) . . ?
O3 C7 O4 123.7(4) . . ?
O3 C7 C6 123.1(3) . . ?
O4 C7 C6 113.1(3) . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
O1 Zn1 N3 C1 -155.8(3) . . . . ?
N1 Zn1 N3 C1 -20.5(3) 4_566 . . . ?
N2 Zn1 N3 C1 92.9(3) 2_644 . . . ?
O1 Zn1 N3 C2 16.9(3) . . . . ?
N1 Zn1 N3 C2 152.1(3) 4_566 . . . ?
N2 Zn1 N3 C2 -94.5(3) 2_644 . . . ?
N3 Zn1 O1 C3 73.4(3) . . . . ?
N1 Zn1 O1 C3 -53.6(3) 4_566 . . . ?
N2 Zn1 O1 C3 -170.5(2) 2_644 . . . ?
C2 N1 N2 C1 0.5(3) . . . . ?
Zn1 N1 N2 C1 -177.3(2) 4_565 . . . ?
C2 N1 N2 Zn1 -178.3(2) . . . 2_654 ?
Zn1 N1 N2 Zn1 4.0(4) 4_565 . . 2_654 ?
Zn1 O1 C3 O2 -0.6(4) . . . . ?
Zn1 O1 C3 C4 176.6(2) . . . . ?
C4 C5 C6 C4 -1.0(6) . . . 3_755 ?
C4 C5 C6 C7 176.0(3) . . . . ?
C6 C5 C4 C6 0.9(6) . . . 3_755 ?
C6 C5 C4 C3 -172.3(3) . . . . ?
O1 C3 C4 C5 -69.5(4) . . . . ?
O2 C3 C4 C5 107.8(4) . . . . ?
O1 C3 C4 C6 117.7(4) . . . 3_755 ?
O2 C3 C4 C6 -65.0(5) . . . 3_755 ?
N2 N1 C2 N3 -0.7(4) . . . . ?
Zn1 N1 C2 N3 177.0(2) 4_565 . . . ?
C1 N3 C2 N1 0.6(4) . . . . ?
Zn1 N3 C2 N1 -173.4(2) . . . . ?
N1 N2 C1 N3 -0.1(4) . . . . ?
Zn1 N2 C1 N3 178.7(2) 2_654 . . . ?
C2 N3 C1 N2 -0.3(4) . . . . ?
Zn1 N3 C1 N2 174.0(2) . . . . ?
C9 N4 C10 O5 -0.7(9) . . . . ?
C8 N4 C10 O5 -179.1(6) . . . . ?
C5 C6 C7 O3 24.1(6) . . . . ?
C4 C6 C7 O3 -159.0(4) 3_755 . . . ?
C5 C6 C7 O4 -152.6(4) . . . . ?
C4 C6 C7 O4 24.3(5) 3_755 . . . ?

_diffrn_measured_fraction_theta_max 0.999
_diffrn_reflns_theta_full        25.00
_diffrn_measured_fraction_theta_full 1.000
_refine_diff_density_max         0.804
_refine_diff_density_min         -0.370
_refine_diff_density_rms         0.082
_database_code_depnum_ccdc_archive 'CCDC 962917'
