# Electronic Supplementary Material (ESI) for RSC Advances.
# 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

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C16 H14 N2 O5 Zn'
_chemical_formula_weight         379.66

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   P21/c

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                   11.877(2)
_cell_length_b                   13.855(3)
_cell_length_c                   13.921(3)
_cell_angle_alpha                90.00
_cell_angle_beta                 114.403(2)
_cell_angle_gamma                90.00
_cell_volume                     2086.3(7)
_cell_formula_units_Z            4
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    ?
_cell_measurement_theta_min      ?
_cell_measurement_theta_max      ?

_exptl_crystal_description       ?
_exptl_crystal_colour            ?
_exptl_crystal_size_max          0.24
_exptl_crystal_size_mid          0.22
_exptl_crystal_size_min          0.20
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.209
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             776
_exptl_absorpt_coefficient_mu    1.199
_exptl_absorpt_correction_type   none
_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         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  ?
_diffrn_measurement_method       ?
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            10661
_diffrn_reflns_av_R_equivalents  0.0396
_diffrn_reflns_av_sigmaI/netI    0.0405
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_theta_min         1.88
_diffrn_reflns_theta_max         25.35
_reflns_number_total             3805
_reflns_number_gt                3146
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_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)+(0.0502P)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         3805
_refine_ls_number_parameters     219
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0371
_refine_ls_R_factor_gt           0.0311
_refine_ls_wR_factor_ref         0.0861
_refine_ls_wR_factor_gt          0.0843
_refine_ls_goodness_of_fit_ref   1.023
_refine_ls_restrained_S_all      1.023
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
loop_
_platon_squeeze_void_nr
_platon_squeeze_void_average_x
_platon_squeeze_void_average_y
_platon_squeeze_void_average_z
_platon_squeeze_void_volume
_platon_squeeze_void_count_electrons
_platon_squeeze_void_content
1 0.000 0.000 0.500 328 85 ' '
2 0.000 0.500 0.000 328 85 ' '

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
C1 C 0.4282(2) 0.89565(17) 0.11732(18) 0.0236(5) Uani 1 1 d . . .
C2 C 0.3597(2) 0.83893(16) 0.16884(18) 0.0223(5) Uani 1 1 d . . .
C3 C 0.4164(2) 0.76581(17) 0.24037(18) 0.0239(5) Uani 1 1 d . . .
H3 H 0.5001 0.7532 0.2609 0.029 Uiso 1 1 calc R . .
C4 C 0.3489(2) 0.71144(17) 0.28141(18) 0.0234(5) Uani 1 1 d . . .
C5 C 0.2240(2) 0.73120(17) 0.25240(18) 0.0261(5) Uani 1 1 d . . .
H5 H 0.1783 0.6931 0.2782 0.031 Uiso 1 1 calc R . .
C6 C 0.1676(2) 0.80781(17) 0.18492(19) 0.0264(5) Uani 1 1 d . . .
C7 C 0.2363(2) 0.86013(17) 0.14282(19) 0.0270(5) Uani 1 1 d . . .
H7 H 0.1989 0.9104 0.0962 0.032 Uiso 1 1 calc R . .
C8 C 0.4100(2) 0.63242(17) 0.35957(19) 0.0251(5) Uani 1 1 d . . .
C9 C 0.0369(2) 0.83539(17) 0.15771(19) 0.0275(5) Uani 1 1 d . . .
C10 C -0.0545(2) 0.76882(18) 0.1458(2) 0.0305(6) Uani 1 1 d . . .
H10 H -0.0350 0.7036 0.1566 0.037 Uiso 1 1 calc R . .
C11 C -0.1741(2) 0.79872(18) 0.11797(19) 0.0289(6) Uani 1 1 d . . .
H11 H -0.2340 0.7524 0.1099 0.035 Uiso 1 1 calc R . .
C12 C -0.1192(2) 0.95654(18) 0.1155(2) 0.0326(6) Uani 1 1 d . . .
H12 H -0.1408 1.0215 0.1059 0.039 Uiso 1 1 calc R . .
C13 C 0.0014(2) 0.93176(18) 0.1427(2) 0.0344(6) Uani 1 1 d . . .
H13 H 0.0599 0.9794 0.1513 0.041 Uiso 1 1 calc R . .
C14 C 0.4595(8) 0.5186(4) 0.1444(5) 0.186(4) Uani 1 1 d . . .
H14A H 0.4627 0.4566 0.1149 0.279 Uiso 1 1 calc R . .
H14B H 0.3867 0.5225 0.1580 0.279 Uiso 1 1 calc R . .
H14C H 0.5315 0.5271 0.2092 0.279 Uiso 1 1 calc R . .
C15 C 0.3249(8) 0.6054(7) 0.0044(5) 0.205(4) Uani 1 1 d . . .
H15A H 0.2957 0.5539 -0.0460 0.308 Uiso 1 1 calc R . .
H15B H 0.3181 0.6655 -0.0320 0.308 Uiso 1 1 calc R . .
H15C H 0.2761 0.6082 0.0447 0.308 Uiso 1 1 calc R . .
C16 C 0.5310(16) 0.6365(5) 0.0500(9) 0.288(9) Uani 1 1 d . . .
H16 H 0.5086 0.6823 -0.0036 0.345 Uiso 1 1 calc R . .
N1 N -0.20819(17) 0.89106(14) 0.10203(15) 0.0240(4) Uani 1 1 d . . .
N2 N 0.4561(5) 0.5880(3) 0.0761(3) 0.0955(13) Uani 1 1 d . . .
O1 O 0.37033(16) 0.96393(13) 0.05868(15) 0.0360(4) Uani 1 1 d . . .
O2 O 0.53649(15) 0.87016(12) 0.13481(14) 0.0322(4) Uani 1 1 d . . .
O3 O 0.51896(16) 0.64698(12) 0.42483(13) 0.0323(4) Uani 1 1 d . . .
O4 O 0.34662(16) 0.55809(12) 0.35318(15) 0.0350(4) Uani 1 1 d . . .
O5 O 0.6575(6) 0.6081(5) 0.1181(7) 0.235(4) Uani 1 1 d . . .
Zn1 Zn 0.61518(2) 0.940250(18) 0.049625(19) 0.01820(10) 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
C1 O1 1.253(3) . ?
C1 O2 1.257(3) . ?
C1 C2 1.508(3) . ?
C2 C3 1.385(3) . ?
C2 C7 1.387(3) . ?
C3 C4 1.384(3) . ?
C3 H3 0.9300 . ?
C4 C5 1.394(3) . ?
C4 C8 1.502(3) . ?
C5 C6 1.392(3) . ?
C5 H5 0.9300 . ?
C6 C7 1.390(3) . ?
C6 C9 1.488(3) . ?
C7 H7 0.9300 . ?
C8 O3 1.253(3) . ?
C8 O4 1.257(3) . ?
C9 C10 1.381(3) . ?
C9 C13 1.390(3) . ?
C10 C11 1.372(3) . ?
C10 H10 0.9300 . ?
C11 N1 1.333(3) . ?
C11 H11 0.9300 . ?
C12 N1 1.346(3) . ?
C12 C13 1.366(3) . ?
C12 H12 0.9300 . ?
C13 H13 0.9300 . ?
C14 N2 1.340(6) . ?
C14 H14A 0.9600 . ?
C14 H14B 0.9600 . ?
C14 H14C 0.9600 . ?
C15 N2 1.482(8) . ?
C15 H15A 0.9600 . ?
C15 H15B 0.9600 . ?
C15 H15C 0.9600 . ?
C16 N2 1.283(10) . ?
C16 O5 1.461(17) . ?
C16 H16 0.9300 . ?
N1 Zn1 2.0331(19) 1_455 ?
O1 Zn1 2.0688(17) 3_675 ?
O2 Zn1 2.0344(16) . ?
O3 Zn1 2.0358(16) 4_576 ?
O4 Zn1 2.0481(17) 2_645 ?
Zn1 N1 2.0331(19) 1_655 ?
Zn1 O3 2.0358(16) 4_575 ?
Zn1 O4 2.0481(17) 2_655 ?
Zn1 O1 2.0688(17) 3_675 ?
Zn1 Zn1 3.0021(7) 3_675 ?

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 C1 O2 125.4(2) . . ?
O1 C1 C2 116.4(2) . . ?
O2 C1 C2 118.1(2) . . ?
C3 C2 C7 119.4(2) . . ?
C3 C2 C1 121.7(2) . . ?
C7 C2 C1 119.0(2) . . ?
C2 C3 C4 120.1(2) . . ?
C2 C3 H3 119.9 . . ?
C4 C3 H3 119.9 . . ?
C3 C4 C5 120.1(2) . . ?
C3 C4 C8 120.5(2) . . ?
C5 C4 C8 119.4(2) . . ?
C6 C5 C4 120.2(2) . . ?
C6 C5 H5 119.9 . . ?
C4 C5 H5 119.9 . . ?
C7 C6 C5 118.6(2) . . ?
C7 C6 C9 119.5(2) . . ?
C5 C6 C9 121.9(2) . . ?
C2 C7 C6 121.4(2) . . ?
C2 C7 H7 119.3 . . ?
C6 C7 H7 119.3 . . ?
O3 C8 O4 126.3(2) . . ?
O3 C8 C4 116.9(2) . . ?
O4 C8 C4 116.8(2) . . ?
C10 C9 C13 116.7(2) . . ?
C10 C9 C6 123.0(2) . . ?
C13 C9 C6 120.3(2) . . ?
C11 C10 C9 120.2(2) . . ?
C11 C10 H10 119.9 . . ?
C9 C10 H10 119.9 . . ?
N1 C11 C10 123.0(2) . . ?
N1 C11 H11 118.5 . . ?
C10 C11 H11 118.5 . . ?
N1 C12 C13 122.9(2) . . ?
N1 C12 H12 118.6 . . ?
C13 C12 H12 118.6 . . ?
C12 C13 C9 120.1(2) . . ?
C12 C13 H13 120.0 . . ?
C9 C13 H13 120.0 . . ?
N2 C14 H14A 109.5 . . ?
N2 C14 H14B 109.5 . . ?
H14A C14 H14B 109.5 . . ?
N2 C14 H14C 109.5 . . ?
H14A C14 H14C 109.5 . . ?
H14B C14 H14C 109.5 . . ?
N2 C15 H15A 109.5 . . ?
N2 C15 H15B 109.5 . . ?
H15A C15 H15B 109.5 . . ?
N2 C15 H15C 109.5 . . ?
H15A C15 H15C 109.5 . . ?
H15B C15 H15C 109.5 . . ?
N2 C16 O5 108.8(8) . . ?
N2 C16 H16 125.6 . . ?
O5 C16 H16 125.6 . . ?
C11 N1 C12 117.2(2) . . ?
C11 N1 Zn1 125.40(16) . 1_455 ?
C12 N1 Zn1 117.29(16) . 1_455 ?
C16 N2 C14 139.1(9) . . ?
C16 N2 C15 112.5(8) . . ?
C14 N2 C15 108.1(6) . . ?
C1 O1 Zn1 140.45(16) . 3_675 ?
C1 O2 Zn1 115.65(15) . . ?
C8 O3 Zn1 124.80(15) . 4_576 ?
C8 O4 Zn1 130.08(17) . 2_645 ?
N1 Zn1 O2 106.57(7) 1_655 . ?
N1 Zn1 O3 103.85(7) 1_655 4_575 ?
O2 Zn1 O3 89.02(7) . 4_575 ?
N1 Zn1 O4 96.66(8) 1_655 2_655 ?
O2 Zn1 O4 91.44(8) . 2_655 ?
O3 Zn1 O4 158.44(7) 4_575 2_655 ?
N1 Zn1 O1 95.30(7) 1_655 3_675 ?
O2 Zn1 O1 158.09(7) . 3_675 ?
O3 Zn1 O1 86.87(8) 4_575 3_675 ?
O4 Zn1 O1 84.69(8) 2_655 3_675 ?
N1 Zn1 Zn1 163.57(6) 1_655 3_675 ?
O2 Zn1 Zn1 88.90(5) . 3_675 ?
O3 Zn1 Zn1 81.44(5) 4_575 3_675 ?
O4 Zn1 Zn1 77.02(5) 2_655 3_675 ?
O1 Zn1 Zn1 69.21(5) 3_675 3_675 ?

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 C1 C2 C3 -175.9(2) . . . . ?
O2 C1 C2 C3 5.3(3) . . . . ?
O1 C1 C2 C7 4.8(3) . . . . ?
O2 C1 C2 C7 -174.0(2) . . . . ?
C7 C2 C3 C4 3.1(3) . . . . ?
C1 C2 C3 C4 -176.2(2) . . . . ?
C2 C3 C4 C5 -1.2(3) . . . . ?
C2 C3 C4 C8 -179.6(2) . . . . ?
C3 C4 C5 C6 -2.2(4) . . . . ?
C8 C4 C5 C6 176.2(2) . . . . ?
C4 C5 C6 C7 3.6(4) . . . . ?
C4 C5 C6 C9 -175.9(2) . . . . ?
C3 C2 C7 C6 -1.7(4) . . . . ?
C1 C2 C7 C6 177.6(2) . . . . ?
C5 C6 C7 C2 -1.6(4) . . . . ?
C9 C6 C7 C2 177.8(2) . . . . ?
C3 C4 C8 O3 36.3(3) . . . . ?
C5 C4 C8 O3 -142.1(2) . . . . ?
C3 C4 C8 O4 -143.7(2) . . . . ?
C5 C4 C8 O4 37.8(3) . . . . ?
C7 C6 C9 C10 145.2(3) . . . . ?
C5 C6 C9 C10 -35.4(4) . . . . ?
C7 C6 C9 C13 -34.7(4) . . . . ?
C5 C6 C9 C13 144.8(3) . . . . ?
C13 C9 C10 C11 1.5(4) . . . . ?
C6 C9 C10 C11 -178.3(2) . . . . ?
C9 C10 C11 N1 -0.5(4) . . . . ?
N1 C12 C13 C9 0.0(4) . . . . ?
C10 C9 C13 C12 -1.3(4) . . . . ?
C6 C9 C13 C12 178.6(2) . . . . ?
C10 C11 N1 C12 -0.8(4) . . . . ?
C10 C11 N1 Zn1 174.89(18) . . . 1_455 ?
C13 C12 N1 C11 1.0(4) . . . . ?
C13 C12 N1 Zn1 -175.0(2) . . . 1_455 ?
O5 C16 N2 C14 -2.1(11) . . . . ?
O5 C16 N2 C15 -174.6(7) . . . . ?
O2 C1 O1 Zn1 8.9(4) . . . 3_675 ?
C2 C1 O1 Zn1 -169.83(18) . . . 3_675 ?
O1 C1 O2 Zn1 -5.4(3) . . . . ?
C2 C1 O2 Zn1 173.29(15) . . . . ?
O4 C8 O3 Zn1 -7.8(4) . . . 4_576 ?
C4 C8 O3 Zn1 172.11(14) . . . 4_576 ?
O3 C8 O4 Zn1 6.7(4) . . . 2_645 ?
C4 C8 O4 Zn1 -173.25(15) . . . 2_645 ?
C1 O2 Zn1 N1 176.05(17) . . . 1_655 ?
C1 O2 Zn1 O3 -79.78(17) . . . 4_575 ?
C1 O2 Zn1 O4 78.66(18) . . . 2_655 ?
C1 O2 Zn1 O1 -0.7(3) . . . 3_675 ?
C1 O2 Zn1 Zn1 1.67(17) . . . 3_675 ?

_diffrn_measured_fraction_theta_max 0.994
_diffrn_reflns_theta_full        25.35
_diffrn_measured_fraction_theta_full 0.994
_refine_diff_density_max         0.584
_refine_diff_density_min         -0.367
_refine_diff_density_rms         0.058
_database_code_depnum_ccdc_archive 'CCDC 946740'
#######################################################################
#
#                 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         ?
_chemical_formula_sum            'C3.67 H3 N0.33 O0.83 Zn0.17'
_chemical_formula_weight         75.96

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   P21/c

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                   15.3645(11)
_cell_length_b                   15.1275(11)
_cell_length_c                   8.3110(6)
_cell_angle_alpha                90.00
_cell_angle_beta                 91.8500(10)
_cell_angle_gamma                90.00
_cell_volume                     1930.7(2)
_cell_formula_units_Z            24
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    ?
_cell_measurement_theta_min      ?
_cell_measurement_theta_max      ?

_exptl_crystal_description       ?
_exptl_crystal_colour            ?
_exptl_crystal_size_max          0.28
_exptl_crystal_size_mid          0.24
_exptl_crystal_size_min          0.22
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.568
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             936
_exptl_absorpt_coefficient_mu    1.311
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.7104
_exptl_absorpt_correction_T_max  0.7614
_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         '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            13743
_diffrn_reflns_av_R_equivalents  0.1027
_diffrn_reflns_av_sigmaI/netI    0.0580
_diffrn_reflns_limit_h_min       -20
_diffrn_reflns_limit_h_max       20
_diffrn_reflns_limit_k_min       -19
_diffrn_reflns_limit_k_max       20
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_limit_l_max       7
_diffrn_reflns_theta_min         1.33
_diffrn_reflns_theta_max         28.39
_reflns_number_total             4819
_reflns_number_gt                3756
_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)+(0.1092P)²+0.2212P] 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         4819
_refine_ls_number_parameters     274
_refine_ls_number_restraints     6
_refine_ls_R_factor_all          0.0615
_refine_ls_R_factor_gt           0.0523
_refine_ls_wR_factor_ref         0.1713
_refine_ls_wR_factor_gt          0.1637
_refine_ls_goodness_of_fit_ref   1.055
_refine_ls_restrained_S_all      1.070
_refine_ls_shift/su_max          0.002
_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
C1 C 0.31891(13) 1.08566(14) 0.9485(3) 0.0284(4) Uani 1 1 d . . .
H1 H 0.3654 1.1168 0.9075 0.034 Uiso 1 1 calc R . .
C2 C 0.32046(13) 0.99369(14) 0.9418(3) 0.0265(4) Uani 1 1 d . . .
C3 C 0.24856(10) 0.94827(16) 0.9986(2) 0.0295(5) Uani 1 1 d . . .
H3 H 0.2469 0.8869 0.9939 0.035 Uiso 1 1 calc R . .
C4 C 0.17920(13) 0.99466(13) 1.0624(3) 0.0253(4) Uani 1 1 d . . .
C5 C 0.18564(13) 1.08643(14) 1.0696(3) 0.0276(4) Uani 1 1 d . . .
H5 H 0.1412 1.1180 1.1165 0.033 Uiso 1 1 calc R . .
C6 C 0.39708(13) 0.94669(14) 0.8789(3) 0.0289(4) Uani 1 1 d . . .
C7 C 0.44677(15) 0.98402(16) 0.7578(3) 0.0356(5) Uani 1 1 d . . .
H7 H 0.4317 1.0389 0.7149 0.043 Uiso 1 1 calc R . .
C8 C 0.51850(14) 0.93901(17) 0.7021(3) 0.0363(5) Uani 1 1 d . . .
H8 H 0.5510 0.9641 0.6214 0.044 Uiso 1 1 calc R . .
C9 C 0.54262(13) 0.85711(15) 0.7645(3) 0.0319(5) Uani 1 1 d . . .
C10 C 0.49321(15) 0.81980(16) 0.8849(3) 0.0397(6) Uani 1 1 d . . .
H10 H 0.5088 0.7651 0.9282 0.048 Uiso 1 1 calc R . .
C11 C 0.42089(15) 0.86391(16) 0.9402(3) 0.0396(6) Uani 1 1 d . . .
H11 H 0.3878 0.8380 1.0193 0.048 Uiso 1 1 calc R . .
C12 C 0.62220(14) 0.80932(16) 0.7091(3) 0.0348(5) Uani 1 1 d . . .
C13 C 0.09982(13) 0.94891(14) 1.1173(3) 0.0284(4) Uani 1 1 d . . .
C14 C 0.05087(15) 0.98305(16) 1.2423(3) 0.0349(5) Uani 1 1 d . . .
H14 H 0.0674 1.0358 1.2920 0.042 Uiso 1 1 calc R . .
C15 C -0.02231(14) 0.93819(17) 1.2919(3) 0.0364(5) Uani 1 1 d . . .
H15 H -0.0545 0.9612 1.3750 0.044 Uiso 1 1 calc R . .
C16 C -0.04834(14) 0.85921(15) 1.2191(3) 0.0326(5) Uani 1 1 d . . .
C17 C -0.00002(15) 0.82549(16) 1.0945(3) 0.0383(5) Uani 1 1 d . . .
H17 H -0.0169 0.7728 1.0450 0.046 Uiso 1 1 calc R . .
C18 C 0.07309(14) 0.86973(16) 1.0434(3) 0.0359(5) Uani 1 1 d . . .
H18 H 0.1046 0.8467 0.9595 0.043 Uiso 1 1 calc R . .
C19 C -0.12871(14) 0.81102(16) 1.2704(3) 0.0350(5) Uani 1 1 d . . .
N1 N 0.25331(9) 1.13139(14) 1.01161(19) 0.0281(4) Uani 1 1 d . . .
O1 O -0.16773(12) 0.84231(15) 1.3889(2) 0.0482(5) Uani 1 1 d . . .
O2 O -0.15221(13) 0.74259(13) 1.1949(3) 0.0441(5) Uani 1 1 d . . .
O3 O 0.65994(12) 0.84146(15) 0.5897(2) 0.0477(5) Uani 1 1 d . . .
O4 O 0.64650(13) 0.74045(13) 0.7822(3) 0.0425(5) Uani 1 1 d . . .
C20 C 0.1999(4) 0.8038(5) 0.3714(11) 0.154(3) Uani 1 1 d . . .
H20 H 0.1417 0.8004 0.3979 0.185 Uiso 1 1 calc R . .
C21 C 0.2139(5) 0.9172(8) 0.5462(9) 0.198(4) Uani 1 1 d U . .
H21A H 0.1532 0.9028 0.5508 0.297 Uiso 1 1 calc R . .
H21B H 0.2201 0.9791 0.5234 0.297 Uiso 1 1 calc R . .
H21C H 0.2423 0.9039 0.6479 0.297 Uiso 1 1 calc R . .
C22 C 0.3347(4) 0.8705(5) 0.4035(11) 0.187(4) Uani 1 1 d . . .
H22A H 0.3669 0.8524 0.4989 0.281 Uiso 1 1 calc R . .
H22B H 0.3526 0.9289 0.3737 0.281 Uiso 1 1 calc R . .
H22C H 0.3459 0.8302 0.3175 0.281 Uiso 1 1 calc R . .
O5 O 0.2311(4) 0.7452(2) 0.2779(7) 0.177(3) Uani 1 1 d . . .
N2 N 0.2494(3) 0.8707(3) 0.4323(6) 0.0906(11) Uani 1 1 d . . .
Zn1 Zn 0.254101(15) 1.267278(17) 1.01296(4) 0.03586(16) 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
C1 N1 1.343(2) . ?
C1 C2 1.393(3) . ?
C2 C3 1.396(3) . ?
C2 C6 1.485(3) . ?
C3 C4 1.395(3) . ?
C4 C5 1.393(3) . ?
C4 C13 1.487(3) . ?
C5 N1 1.345(2) . ?
C6 C11 1.397(3) . ?
C6 C7 1.401(3) . ?
C7 C8 1.388(3) . ?
C8 C9 1.389(3) . ?
C9 C10 1.394(3) . ?
C9 C12 1.506(3) . ?
C10 C11 1.387(3) . ?
C12 O4 1.257(3) . ?
C12 O3 1.263(3) . ?
C13 C14 1.400(3) . ?
C13 C18 1.402(3) . ?
C14 C15 1.387(3) . ?
C15 C16 1.392(3) . ?
C16 C17 1.391(3) . ?
C16 C19 1.507(3) . ?
C17 C18 1.386(3) . ?
C19 O2 1.257(3) . ?
C19 O1 1.262(3) . ?
N1 Zn1 2.056(2) . ?
O1 Zn1 1.9453(18) 2_547 ?
O2 Zn1 2.298(2) 3_577 ?
O3 Zn1 1.9505(18) 2_646 ?
O4 Zn1 2.253(2) 3_677 ?
C20 O5 1.283(9) . ?
C20 N2 1.354(7) . ?
C21 N2 1.313(8) . ?
C22 N2 1.340(7) . ?
Zn1 O1 1.9453(18) 2_557 ?
Zn1 O3 1.9506(18) 2_656 ?
Zn1 O4 2.253(2) 3_677 ?
Zn1 O2 2.298(2) 3_577 ?

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
N1 C1 C2 122.99(19) . . ?
C1 C2 C3 117.59(19) . . ?
C1 C2 C6 120.50(18) . . ?
C3 C2 C6 121.90(18) . . ?
C4 C3 C2 120.2(2) . . ?
C5 C4 C3 117.61(18) . . ?
C5 C4 C13 120.58(18) . . ?
C3 C4 C13 121.79(18) . . ?
N1 C5 C4 122.92(19) . . ?
C11 C6 C7 118.8(2) . . ?
C11 C6 C2 120.15(19) . . ?
C7 C6 C2 121.09(19) . . ?
C8 C7 C6 119.9(2) . . ?
C7 C8 C9 121.2(2) . . ?
C8 C9 C10 119.0(2) . . ?
C8 C9 C12 121.6(2) . . ?
C10 C9 C12 119.4(2) . . ?
C11 C10 C9 120.2(2) . . ?
C10 C11 C6 120.9(2) . . ?
O4 C12 O3 124.2(2) . . ?
O4 C12 C9 118.8(2) . . ?
O3 C12 C9 117.0(2) . . ?
C14 C13 C18 118.91(19) . . ?
C14 C13 C4 121.43(19) . . ?
C18 C13 C4 119.67(19) . . ?
C15 C14 C13 120.0(2) . . ?
C14 C15 C16 121.0(2) . . ?
C17 C16 C15 119.1(2) . . ?
C17 C16 C19 119.7(2) . . ?
C15 C16 C19 121.3(2) . . ?
C18 C17 C16 120.6(2) . . ?
C17 C18 C13 120.5(2) . . ?
O2 C19 O1 124.2(2) . . ?
O2 C19 C16 118.8(2) . . ?
O1 C19 C16 117.0(2) . . ?
C1 N1 C5 118.6(2) . . ?
C1 N1 Zn1 120.86(13) . . ?
C5 N1 Zn1 120.55(13) . . ?
C19 O1 Zn1 117.13(17) . 2_547 ?
C19 O2 Zn1 127.31(18) . 3_577 ?
C12 O3 Zn1 117.18(17) . 2_646 ?
C12 O4 Zn1 126.30(17) . 3_677 ?
O5 C20 N2 121.8(6) . . ?
C21 N2 C22 124.2(6) . . ?
C21 N2 C20 115.4(7) . . ?
C22 N2 C20 118.2(6) . . ?
O1 Zn1 O3 109.17(12) 2_557 2_656 ?
O1 Zn1 N1 125.58(8) 2_557 . ?
O3 Zn1 N1 125.23(7) 2_656 . ?
O1 Zn1 O4 99.70(8) 2_557 3_677 ?
O3 Zn1 O4 84.74(9) 2_656 3_677 ?
N1 Zn1 O4 87.48(7) . 3_677 ?
O1 Zn1 O2 84.01(9) 2_557 3_577 ?
O3 Zn1 O2 99.38(8) 2_656 3_577 ?
N1 Zn1 O2 85.82(7) . 3_577 ?
O4 Zn1 O2 173.29(9) 3_677 3_577 ?

_diffrn_measured_fraction_theta_max 0.998
_diffrn_reflns_theta_full        28.39
_diffrn_measured_fraction_theta_full 0.998
_refine_diff_density_max         1.221
_refine_diff_density_min         -0.903
_refine_diff_density_rms         0.112
_database_code_depnum_ccdc_archive 'CCDC 946741'
