# Electronic Supplementary Material (ESI) for Dalton Transactions
# This journal is © The Royal Society of Chemistry 2013

#######################################################################
#
#                 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_nnia
#TrackingRef 'CIF-1.cif'



_refine_ls_number_constraints    ?
#Added by publCIF
_cell_special_details            ?
#Added by publCIF
_symmetry_space_group_name_hall  'P 2yb'
#Added by publCIF
_audit_update_record             
;
2012-03-23 # Formatted by publCIF
;
_audit_creation_method           SHELXL-97
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C21 H22 N4 O3'
_chemical_formula_sum            'C21 H22 N4 O3'
_chemical_formula_weight         378.43
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'

_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_H-M   'P 21'
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y+1/2, -z'

_cell_length_a                   6.3154(4)
_cell_length_b                   12.2970(7)
_cell_length_c                   12.3905(9)
_cell_angle_alpha                90.00
_cell_angle_beta                 97.703(7)
_cell_angle_gamma                90.00
_cell_volume                     953.57(11)
_cell_formula_units_Z            2
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    1210
_cell_measurement_theta_min      3.2485
_cell_measurement_theta_max      28.8357

_exptl_crystal_description       Block
_exptl_crystal_colour            RED
_exptl_crystal_size_max          0.4
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.2
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.318
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             400
_exptl_absorpt_coefficient_mu    0.090
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.97190
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_process_details   
;
CrysAlisPro, Agilent Technologies,
Version 1.171.34.49 (release 20-01-2011 CrysAlis171 .NET)
(compiled Jan 20 2011,15:58:25)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_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  Xcalibur,Eos
_diffrn_measurement_method       \wscans
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            4028
_diffrn_reflns_av_R_equivalents  0.0199
_diffrn_reflns_av_sigmaI/netI    0.0571
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_theta_min         3.26
_diffrn_reflns_theta_max         28.90
_reflns_number_total             3058
_reflns_number_gt                2031
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.34.49 (release 20-01-2011 CrysAlis171 .NET)
(compiled Jan 20 2011,15:58:25)
;
_computing_cell_refinement       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.34.49 (release 20-01-2011 CrysAlis171 .NET)
(compiled Jan 20 2011,15:58:25)
;
_computing_data_reduction        
;
CrysAlisPro, Agilent Technologies,
Version 1.171.34.49 (release 20-01-2011 CrysAlis171 .NET)
(compiled Jan 20 2011,15:58:25)
;

_computing_structure_solution    'A short history of SHELX (Sheldrick, 2007)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    
;
O. V. Dolomanov, L. J. Bourhis, R. J. Gildea, J. A. K. Howard and H. Puschmann,
OLEX2: a complete structure solution, refinement and analysis program.
J. Appl. Cryst. (2009). 42, 339-341.
;
_computing_publication_material  
;
O. V. Dolomanov, L. J. Bourhis, R. J. Gildea, J. A. K. Howard and H. Puschmann,
OLEX2: a complete structure solution, refinement and analysis program.
J. Appl. Cryst. (2009). 42, 339-341.
;

_refine_special_details          
;
Refinement of F^2^ against ALL reflections. The weighted R-factor wR and
goodness of fit S are based on F^2^, conventional R-factors R are based
on F, with F set to zero for negative F^2^. The threshold expression of
F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is
not relevant to the choice of reflections for refinement. R-factors based
on F^2^ 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/[\s^2^(Fo^2^)+(0.0577P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    ?
_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   2.8(18)
_refine_ls_number_reflns         3058
_refine_ls_number_parameters     256
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0937
_refine_ls_R_factor_gt           0.0546
_refine_ls_wR_factor_ref         0.1340
_refine_ls_wR_factor_gt          0.1123
_refine_ls_goodness_of_fit_ref   1.028
_refine_ls_restrained_S_all      1.028
_refine_ls_shift/su_max          0.000
_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
O1 O 0.5195(4) 0.34738(18) 0.3635(2) 0.0395(6) Uani 1 1 d . . .
O2 O 0.2533(4) 0.2940(2) 0.4470(2) 0.0465(7) Uani 1 1 d . . .
N2 N 0.1008(4) 0.4257(2) 0.5870(2) 0.0371(7) Uani 1 1 d . . .
N3 N -0.0327(5) 0.4395(3) 0.6645(3) 0.0433(8) Uani 1 1 d . . .
H4 H -0.0243 0.4918 0.7110 0.052 Uiso 1 1 calc R . .
C12 C 0.3984(5) 0.4690(3) 0.4962(3) 0.0332(8) Uani 1 1 d . . .
C13 C 0.3804(6) 0.3658(3) 0.4384(3) 0.0379(9) Uani 1 1 d . . .
C8 C 0.6992(5) 0.5172(3) 0.4030(3) 0.0342(8) Uani 1 1 d . . .
C10 C 0.8039(6) 0.3899(3) 0.2693(3) 0.0385(9) Uani 1 1 d . . .
H8 H 0.7828 0.3234 0.2337 0.046 Uiso 1 1 calc R . .
N1 N 1.0952(5) 0.4348(3) 0.1684(3) 0.0468(8) Uani 1 1 d . . .
C16 C -0.1773(5) 0.3601(3) 0.6575(3) 0.0361(8) Uani 1 1 d . . .
C11 C 0.5573(5) 0.5399(3) 0.4772(3) 0.0378(9) Uani 1 1 d . . .
H11 H 0.5706 0.6054 0.5150 0.045 Uiso 1 1 calc R . .
O3 O -0.2021(4) 0.2876(2) 0.5867(2) 0.0490(7) Uani 1 1 d . . .
C5 C 0.9657(5) 0.4602(3) 0.2442(3) 0.0394(9) Uani 1 1 d . . .
C9 C 0.6771(5) 0.4188(3) 0.3462(3) 0.0357(8) Uani 1 1 d . . .
C14 C 0.2534(6) 0.4940(3) 0.5747(3) 0.0391(9) Uani 1 1 d . . .
C17 C -0.3166(6) 0.3642(3) 0.7463(3) 0.0384(8) Uani 1 1 d . . .
C6 C 0.9936(5) 0.5596(3) 0.3036(3) 0.0403(9) Uani 1 1 d . . .
H17 H 1.1016 0.6072 0.2903 0.048 Uiso 1 1 calc R . .
C7 C 0.8650(5) 0.5863(3) 0.3796(3) 0.0406(9) Uani 1 1 d . . .
H18 H 0.8875 0.6517 0.4170 0.049 Uiso 1 1 calc R . .
C2 C 1.2671(6) 0.5065(3) 0.1438(3) 0.0489(10) Uani 1 1 d . . .
H19A H 1.3778 0.4629 0.1177 0.059 Uiso 1 1 calc R . .
H19B H 1.3296 0.5422 0.2103 0.059 Uiso 1 1 calc R . .
C18 C -0.2776(7) 0.4336(4) 0.8332(3) 0.0613(12) Uani 1 1 d . . .
H20 H -0.1631 0.4817 0.8381 0.074 Uiso 1 1 calc R . .
C21 C -0.4913(6) 0.2972(3) 0.7429(3) 0.0501(10) Uani 1 1 d . . .
H21 H -0.5248 0.2492 0.6852 0.060 Uiso 1 1 calc R . .
N4 N -0.5794(6) 0.3682(4) 0.9111(3) 0.0754(12) Uani 1 1 d . . .
C1 C 1.1938(7) 0.5914(4) 0.0602(4) 0.0718(14) Uani 1 1 d . . .
H23A H 1.1405 0.5568 -0.0074 0.108 Uiso 1 1 calc R . .
H23B H 1.3117 0.6377 0.0498 0.108 Uiso 1 1 calc R . .
H23C H 1.0824 0.6341 0.0848 0.108 Uiso 1 1 calc R . .
C20 C -0.6172(7) 0.3016(5) 0.8260(4) 0.0702(14) Uani 1 1 d . . .
H24 H -0.7346 0.2554 0.8222 0.084 Uiso 1 1 calc R . .
C19 C -0.4093(8) 0.4315(5) 0.9132(4) 0.0818(16) Uani 1 1 d . . .
H25 H -0.3767 0.4776 0.9726 0.098 Uiso 1 1 calc R . .
C3 C 1.0623(6) 0.3356(3) 0.1021(3) 0.0518(11) Uani 1 1 d . . .
H26A H 1.1014 0.3499 0.0303 0.062 Uiso 1 1 calc R . .
H26B H 0.9120 0.3163 0.0933 0.062 Uiso 1 1 calc R . .
C15 C 0.2753(7) 0.5958(3) 0.6398(4) 0.0643(13) Uani 1 1 d . . .
H27A H 0.2423 0.6571 0.5925 0.096 Uiso 1 1 calc R . .
H27B H 0.4192 0.6021 0.6757 0.096 Uiso 1 1 calc R . .
H27C H 0.1784 0.5940 0.6933 0.096 Uiso 1 1 calc R . .
C4 C 1.1917(8) 0.2419(4) 0.1524(4) 0.0743(14) Uani 1 1 d . . .
H28A H 1.1622 0.1784 0.1078 0.111 Uiso 1 1 calc R . .
H28B H 1.1547 0.2280 0.2238 0.111 Uiso 1 1 calc R . .
H28C H 1.3409 0.2592 0.1578 0.111 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
O1 0.0423(14) 0.0329(14) 0.0451(15) -0.0028(12) 0.0129(11) -0.0064(12)
O2 0.0512(15) 0.0350(14) 0.0565(17) -0.0018(13) 0.0182(13) -0.0117(13)
N2 0.0342(16) 0.0385(17) 0.0399(18) 0.0063(14) 0.0098(14) 0.0004(15)
N3 0.0479(17) 0.0417(18) 0.0438(19) -0.0089(14) 0.0185(16) 0.0001(16)
C12 0.0328(18) 0.0286(18) 0.039(2) 0.0023(16) 0.0075(16) 0.0016(16)
C13 0.043(2) 0.036(2) 0.035(2) 0.0009(17) 0.0076(17) 0.0059(19)
C8 0.0321(19) 0.0276(19) 0.043(2) 0.0018(16) 0.0063(17) 0.0023(15)
C10 0.041(2) 0.033(2) 0.042(2) -0.0043(17) 0.0057(18) 0.0031(17)
N1 0.0483(19) 0.045(2) 0.051(2) -0.0033(17) 0.0173(17) 0.0005(17)
C16 0.036(2) 0.0302(19) 0.043(2) 0.0082(18) 0.0090(16) 0.0030(18)
C11 0.045(2) 0.0290(18) 0.040(2) -0.0007(16) 0.0051(17) 0.0023(17)
O3 0.0515(16) 0.0428(15) 0.0550(17) -0.0086(14) 0.0154(13) -0.0012(13)
C5 0.0353(19) 0.040(2) 0.044(2) 0.0028(17) 0.0080(18) 0.0041(17)
C9 0.037(2) 0.0314(19) 0.038(2) 0.0037(16) 0.0032(17) 0.0024(17)
C14 0.041(2) 0.037(2) 0.040(2) 0.0047(17) 0.0051(18) 0.0010(19)
C17 0.0386(19) 0.038(2) 0.038(2) 0.0032(17) 0.0042(16) 0.0006(18)
C6 0.035(2) 0.036(2) 0.051(3) 0.0031(18) 0.0100(18) -0.0035(17)
C7 0.042(2) 0.036(2) 0.045(2) -0.0004(18) 0.0059(17) 0.0017(18)
C2 0.043(2) 0.054(3) 0.053(3) 0.004(2) 0.018(2) 0.005(2)
C18 0.064(3) 0.069(3) 0.054(3) -0.011(2) 0.022(2) -0.015(2)
C21 0.048(2) 0.051(2) 0.052(3) -0.005(2) 0.011(2) -0.004(2)
N4 0.073(3) 0.093(3) 0.066(3) -0.003(2) 0.033(2) -0.009(3)
C1 0.082(3) 0.076(3) 0.057(3) 0.021(3) 0.009(2) -0.004(3)
C20 0.056(3) 0.087(4) 0.071(3) 0.011(3) 0.022(3) -0.015(3)
C19 0.085(4) 0.099(4) 0.067(3) -0.022(3) 0.031(3) -0.024(3)
C3 0.052(2) 0.060(3) 0.046(2) -0.006(2) 0.012(2) -0.002(2)
C15 0.075(3) 0.046(2) 0.080(3) -0.024(2) 0.039(3) -0.015(2)
C4 0.093(4) 0.053(3) 0.074(3) -0.017(2) 0.003(3) 0.008(3)

_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
O1 C9 1.366(4) . ?
O1 C13 1.379(4) . ?
O2 C13 1.208(4) . ?
N2 C14 1.303(4) . ?
N2 N3 1.371(4) . ?
N3 C16 1.331(4) . ?
N3 H4 0.8600 . ?
C12 C11 1.373(5) . ?
C12 C13 1.454(5) . ?
C12 C14 1.456(5) . ?
C8 C11 1.395(5) . ?
C8 C9 1.398(4) . ?
C8 C7 1.408(5) . ?
C10 C9 1.371(5) . ?
C10 C5 1.405(5) . ?
C10 H8 0.9300 . ?
N1 C5 1.361(4) . ?
N1 C2 1.462(5) . ?
N1 C3 1.470(5) . ?
C16 O3 1.245(4) . ?
C16 C17 1.500(5) . ?
C11 H11 0.9300 . ?
C5 C6 1.426(5) . ?
C14 C15 1.485(5) . ?
C17 C18 1.370(5) . ?
C17 C21 1.373(5) . ?
C6 C7 1.363(5) . ?
C6 H17 0.9300 . ?
C7 H18 0.9300 . ?
C2 C1 1.500(6) . ?
C2 H19A 0.9700 . ?
C2 H19B 0.9700 . ?
C18 C19 1.377(6) . ?
C18 H20 0.9300 . ?
C21 C20 1.383(5) . ?
C21 H21 0.9300 . ?
N4 C19 1.325(6) . ?
N4 C20 1.331(6) . ?
C1 H23A 0.9600 . ?
C1 H23B 0.9600 . ?
C1 H23C 0.9600 . ?
C20 H24 0.9300 . ?
C19 H25 0.9300 . ?
C3 C4 1.500(6) . ?
C3 H26A 0.9700 . ?
C3 H26B 0.9700 . ?
C15 H27A 0.9600 . ?
C15 H27B 0.9600 . ?
C15 H27C 0.9600 . ?
C4 H28A 0.9600 . ?
C4 H28B 0.9600 . ?
C4 H28C 0.9600 . ?

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
C9 O1 C13 122.9(3) . . ?
C14 N2 N3 122.4(3) . . ?
C16 N3 N2 110.1(3) . . ?
C16 N3 H4 124.9 . . ?
N2 N3 H4 124.9 . . ?
C11 C12 C13 118.7(3) . . ?
C11 C12 C14 121.3(3) . . ?
C13 C12 C14 120.0(3) . . ?
O2 C13 O1 115.5(3) . . ?
O2 C13 C12 127.1(3) . . ?
O1 C13 C12 117.4(3) . . ?
C11 C8 C9 118.4(3) . . ?
C11 C8 C7 125.2(3) . . ?
C9 C8 C7 116.5(3) . . ?
C9 C10 C5 120.3(3) . . ?
C9 C10 H8 119.9 . . ?
C5 C10 H8 119.9 . . ?
C5 N1 C2 122.5(3) . . ?
C5 N1 C3 121.5(3) . . ?
C2 N1 C3 115.9(3) . . ?
O3 C16 N3 126.3(3) . . ?
O3 C16 C17 120.6(3) . . ?
N3 C16 C17 113.1(3) . . ?
C12 C11 C8 122.3(3) . . ?
C12 C11 H11 118.8 . . ?
C8 C11 H11 118.8 . . ?
N1 C5 C10 122.2(3) . . ?
N1 C5 C6 120.6(3) . . ?
C10 C5 C6 117.2(3) . . ?
O1 C9 C10 116.6(3) . . ?
O1 C9 C8 120.2(3) . . ?
C10 C9 C8 123.1(3) . . ?
N2 C14 C12 118.9(3) . . ?
N2 C14 C15 119.8(3) . . ?
C12 C14 C15 121.3(3) . . ?
C18 C17 C21 117.2(4) . . ?
C18 C17 C16 122.5(3) . . ?
C21 C17 C16 120.4(3) . . ?
C7 C6 C5 121.3(3) . . ?
C7 C6 H17 119.4 . . ?
C5 C6 H17 119.4 . . ?
C6 C7 C8 121.7(3) . . ?
C6 C7 H18 119.2 . . ?
C8 C7 H18 119.2 . . ?
N1 C2 C1 113.3(3) . . ?
N1 C2 H19A 108.9 . . ?
C1 C2 H19A 108.9 . . ?
N1 C2 H19B 108.9 . . ?
C1 C2 H19B 108.9 . . ?
H19A C2 H19B 107.7 . . ?
C17 C18 C19 119.5(4) . . ?
C17 C18 H20 120.3 . . ?
C19 C18 H20 120.3 . . ?
C17 C21 C20 119.6(4) . . ?
C17 C21 H21 120.2 . . ?
C20 C21 H21 120.2 . . ?
C19 N4 C20 115.9(4) . . ?
C2 C1 H23A 109.5 . . ?
C2 C1 H23B 109.5 . . ?
H23A C1 H23B 109.5 . . ?
C2 C1 H23C 109.5 . . ?
H23A C1 H23C 109.5 . . ?
H23B C1 H23C 109.5 . . ?
N4 C20 C21 123.6(4) . . ?
N4 C20 H24 118.2 . . ?
C21 C20 H24 118.2 . . ?
N4 C19 C18 124.3(5) . . ?
N4 C19 H25 117.9 . . ?
C18 C19 H25 117.9 . . ?
N1 C3 C4 112.1(3) . . ?
N1 C3 H26A 109.2 . . ?
C4 C3 H26A 109.2 . . ?
N1 C3 H26B 109.2 . . ?
C4 C3 H26B 109.2 . . ?
H26A C3 H26B 107.9 . . ?
C14 C15 H27A 109.5 . . ?
C14 C15 H27B 109.5 . . ?
H27A C15 H27B 109.5 . . ?
C14 C15 H27C 109.5 . . ?
H27A C15 H27C 109.5 . . ?
H27B C15 H27C 109.5 . . ?
C3 C4 H28A 109.5 . . ?
C3 C4 H28B 109.5 . . ?
H28A C4 H28B 109.5 . . ?
C3 C4 H28C 109.5 . . ?
H28A C4 H28C 109.5 . . ?
H28B C4 H28C 109.5 . . ?

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
C14 N2 N3 C16 178.2(3) . . . . ?
C9 O1 C13 O2 -178.0(3) . . . . ?
C9 O1 C13 C12 3.3(5) . . . . ?
C11 C12 C13 O2 178.6(3) . . . . ?
C14 C12 C13 O2 0.3(6) . . . . ?
C11 C12 C13 O1 -2.8(5) . . . . ?
C14 C12 C13 O1 178.8(3) . . . . ?
N2 N3 C16 O3 -5.1(5) . . . . ?
N2 N3 C16 C17 174.8(3) . . . . ?
C13 C12 C11 C8 1.1(5) . . . . ?
C14 C12 C11 C8 179.4(3) . . . . ?
C9 C8 C11 C12 0.3(5) . . . . ?
C7 C8 C11 C12 179.9(3) . . . . ?
C2 N1 C5 C10 -178.5(3) . . . . ?
C3 N1 C5 C10 4.9(5) . . . . ?
C2 N1 C5 C6 -0.1(5) . . . . ?
C3 N1 C5 C6 -176.7(3) . . . . ?
C9 C10 C5 N1 -180.0(3) . . . . ?
C9 C10 C5 C6 1.6(5) . . . . ?
C13 O1 C9 C10 179.9(3) . . . . ?
C13 O1 C9 C8 -2.0(5) . . . . ?
C5 C10 C9 O1 178.1(3) . . . . ?
C5 C10 C9 C8 0.0(5) . . . . ?
C11 C8 C9 O1 0.1(5) . . . . ?
C7 C8 C9 O1 -179.6(3) . . . . ?
C11 C8 C9 C10 178.1(4) . . . . ?
C7 C8 C9 C10 -1.6(5) . . . . ?
N3 N2 C14 C12 175.3(3) . . . . ?
N3 N2 C14 C15 -5.2(5) . . . . ?
C11 C12 C14 N2 177.7(3) . . . . ?
C13 C12 C14 N2 -4.1(5) . . . . ?
C11 C12 C14 C15 -1.8(5) . . . . ?
C13 C12 C14 C15 176.4(4) . . . . ?
O3 C16 C17 C18 171.5(4) . . . . ?
N3 C16 C17 C18 -8.4(5) . . . . ?
O3 C16 C17 C21 -8.7(5) . . . . ?
N3 C16 C17 C21 171.4(3) . . . . ?
N1 C5 C6 C7 179.9(3) . . . . ?
C10 C5 C6 C7 -1.6(5) . . . . ?
C5 C6 C7 C8 0.0(6) . . . . ?
C11 C8 C7 C6 -178.1(4) . . . . ?
C9 C8 C7 C6 1.6(5) . . . . ?
C5 N1 C2 C1 -86.0(5) . . . . ?
C3 N1 C2 C1 90.8(4) . . . . ?
C21 C17 C18 C19 1.5(6) . . . . ?
C16 C17 C18 C19 -178.6(4) . . . . ?
C18 C17 C21 C20 -0.6(6) . . . . ?
C16 C17 C21 C20 179.5(4) . . . . ?
C19 N4 C20 C21 -0.6(8) . . . . ?
C17 C21 C20 N4 0.1(7) . . . . ?
C20 N4 C19 C18 1.6(8) . . . . ?
C17 C18 C19 N4 -2.2(8) . . . . ?
C5 N1 C3 C4 -92.7(4) . . . . ?
C2 N1 C3 C4 90.5(4) . . . . ?

_diffrn_measured_fraction_theta_max 0.862
_diffrn_reflns_theta_full        25.00
_diffrn_measured_fraction_theta_full 0.999
_refine_diff_density_max         0.270
_refine_diff_density_min         -0.239
_refine_diff_density_rms         0.043
_database_code_depnum_ccdc_archive 'CCDC 873620'
#######################################################################
#
#                 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_nnizn
#TrackingRef 'CIF-2.cif'


_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C21 H21 N5 O6 Zn'
_chemical_formula_sum            'C21 H21 N5 O6 Zn'
_chemical_formula_weight         504.80

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           orthorhombic
_symmetry_space_group_name_H-M   'P 21 21 21'

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                   12.3149(17)
_cell_length_b                   12.7297(7)
_cell_length_c                   14.0515(11)
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_volume                     2202.8(4)
_cell_formula_units_Z            4
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    1529
_cell_measurement_theta_min      3.1942
_cell_measurement_theta_max      32.4236

_exptl_crystal_description       BLOCK
_exptl_crystal_colour            RED
_exptl_crystal_size_max          0.32
_exptl_crystal_size_mid          0.24
_exptl_crystal_size_min          0.22
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.522
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1040
_exptl_absorpt_coefficient_mu    1.164
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.86938
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_process_details   
;
CrysAlisPro, Agilent Technologies,
Version 1.171.34.49 (release 20-01-2011 CrysAlis171 .NET)
(compiled Jan 20 2011,15:58:25)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;


_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  'Xcalibur, Eos'
_diffrn_measurement_method       '\w scans'
_diffrn_detector_area_resol_mean 16.0938
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            9340
_diffrn_reflns_av_R_equivalents  0.0621
_diffrn_reflns_av_sigmaI/netI    0.1345
_diffrn_reflns_limit_h_min       -17
_diffrn_reflns_limit_h_max       5
_diffrn_reflns_limit_k_min       -19
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_limit_l_max       8
_diffrn_reflns_theta_min         3.20
_diffrn_reflns_theta_max         32.50
_reflns_number_total             6068
_reflns_number_gt                3386
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.34.49 (release 20-01-2011 CrysAlis171 .NET)
(compiled Jan 20 2011,15:58:25)
;

_computing_cell_refinement       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.34.49 (release 20-01-2011 CrysAlis171 .NET)
(compiled Jan 20 2011,15:58:25)
;

_computing_data_reduction        
;
CrysAlisPro, Agilent Technologies,
Version 1.171.34.49 (release 20-01-2011 CrysAlis171 .NET)
(compiled Jan 20 2011,15:58:25)
;

_computing_structure_solution    ?
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    ?
_computing_publication_material  ?

_refine_special_details          
;
Refinement of F^2^ against ALL reflections. The weighted R-factor wR and
goodness of fit S are based on F^2^, conventional R-factors R are based
on F, with F set to zero for negative F^2^. The threshold expression of
F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is
not relevant to the choice of reflections for refinement. R-factors based
on F^2^ 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/[\s^2^(Fo^2^)+(0.0000P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    riding
_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   0.001(15)
_refine_ls_number_reflns         6068
_refine_ls_number_parameters     301
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1218
_refine_ls_R_factor_gt           0.0566
_refine_ls_wR_factor_ref         0.0816
_refine_ls_wR_factor_gt          0.0626
_refine_ls_goodness_of_fit_ref   0.894
_refine_ls_restrained_S_all      0.894
_refine_ls_shift/su_max          0.000
_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 0.40619(5) 0.85177(3) 0.59746(4) 0.03298(12) Uani 1 1 d . . .
O3 O 0.3777(3) 0.95482(19) 0.7044(2) 0.0385(9) Uani 1 1 d . . .
N2 N 0.3674(3) 0.7498(2) 0.7039(3) 0.0304(10) Uani 1 1 d . . .
O2 O 0.4241(3) 0.71921(16) 0.5123(2) 0.0381(9) Uani 1 1 d . . .
O1 O 0.4510(3) 0.56007(17) 0.4644(2) 0.0369(9) Uani 1 1 d . . .
C5 C 0.4928(4) 0.2850(3) 0.4030(4) 0.0388(12) Uani 1 1 d . . .
N3 N 0.3322(3) 0.8020(2) 0.7858(3) 0.0353(10) Uani 1 1 d . . .
C14 C 0.3757(3) 0.6482(3) 0.7115(3) 0.0287(9) Uani 1 1 d . . .
C17 C 0.2964(4) 0.9651(3) 0.8579(3) 0.0304(11) Uani 1 1 d . . .
C10 C 0.4802(4) 0.3955(3) 0.3958(4) 0.0401(13) Uani 1 1 d . . .
H10 H 0.4869 0.4288 0.3372 0.048 Uiso 1 1 calc R . .
C16 C 0.3399(4) 0.9046(3) 0.7746(3) 0.0320(12) Uani 1 1 d . . .
C21 C 0.2890(4) 1.0726(3) 0.8535(3) 0.0394(13) Uani 1 1 d . . .
H12 H 0.3160 1.1089 0.8011 0.047 Uiso 1 1 calc R . .
C12 C 0.4080(4) 0.5838(3) 0.6304(3) 0.0276(9) Uani 1 1 d . . .
C9 C 0.4583(4) 0.4519(3) 0.4753(3) 0.0330(12) Uani 1 1 d . . .
C6 C 0.4832(4) 0.2412(3) 0.4944(4) 0.0436(14) Uani 1 1 d . . .
H16 H 0.4949 0.1695 0.5020 0.052 Uiso 1 1 calc R . .
C8 C 0.4442(4) 0.4100(3) 0.5644(3) 0.0322(12) Uani 1 1 d . . .
C7 C 0.4576(4) 0.2995(3) 0.5719(3) 0.0376(13) Uani 1 1 d . . .
H18 H 0.4488 0.2669 0.6306 0.045 Uiso 1 1 calc R . .
N1 N 0.5170(4) 0.2261(3) 0.3255(3) 0.0497(13) Uani 1 1 d . . .
O4 O 0.5377(3) 0.9225(3) 0.5348(3) 0.0560(11) Uani 1 1 d . . .
C13 C 0.4253(4) 0.6257(3) 0.5366(3) 0.0316(11) Uani 1 1 d . . .
C20 C 0.2411(4) 1.1261(3) 0.9277(3) 0.0411(13) Uani 1 1 d . . .
H22 H 0.2358 1.1989 0.9234 0.049 Uiso 1 1 calc R . .
C18 C 0.2612(5) 0.9167(3) 0.9387(4) 0.0438(15) Uani 1 1 d . . .
H23 H 0.2681 0.8443 0.9452 0.053 Uiso 1 1 calc R . .
C2 C 0.5260(5) 0.2705(4) 0.2307(4) 0.0572(17) Uani 1 1 d . . .
H25A H 0.5737 0.2267 0.1927 0.069 Uiso 1 1 calc R . .
H25B H 0.5586 0.3397 0.2351 0.069 Uiso 1 1 calc R . .
N4 N 0.2023(3) 1.0797(2) 1.0048(3) 0.0368(11) Uani 1 1 d . . .
C3 C 0.5358(5) 0.1121(3) 0.3339(4) 0.066(2) Uani 1 1 d . . .
H27A H 0.5132 0.0776 0.2756 0.079 Uiso 1 1 calc R . .
H27B H 0.4924 0.0842 0.3857 0.079 Uiso 1 1 calc R . .
C19 C 0.2155(4) 0.9752(3) 1.0107(3) 0.0419(14) Uani 1 1 d . . .
H28 H 0.1928 0.9409 1.0657 0.050 Uiso 1 1 calc R . .
C11 C 0.4185(4) 0.4764(3) 0.6410(3) 0.0316(11) Uani 1 1 d . . .
H29 H 0.4083 0.4470 0.7010 0.038 Uiso 1 1 calc R . .
C15 C 0.3532(5) 0.5940(3) 0.8040(3) 0.0506(17) Uani 1 1 d . . .
H37A H 0.4199 0.5673 0.8298 0.076 Uiso 1 1 calc R . .
H37B H 0.3037 0.5370 0.7935 0.076 Uiso 1 1 calc R . .
H37C H 0.3217 0.6431 0.8479 0.076 Uiso 1 1 calc R . .
O5 O 0.6060(4) 0.8260(2) 0.6456(3) 0.0726(12) Uani 1 1 d . . .
N5 N 0.6215(4) 0.8826(3) 0.5739(4) 0.0584(15) Uani 1 1 d . . .
O6 O 0.7119(3) 0.9026(3) 0.5437(4) 0.0890(17) Uani 1 1 d . . .
C1 C 0.4191(6) 0.2791(4) 0.1826(4) 0.090(2) Uani 1 1 d . . .
H1A H 0.4281 0.3137 0.1224 0.135 Uiso 1 1 calc R . .
H1B H 0.3703 0.3190 0.2217 0.135 Uiso 1 1 calc R . .
H1C H 0.3898 0.2101 0.1725 0.135 Uiso 1 1 calc R . .
C4 C 0.6523(6) 0.0899(5) 0.3520(6) 0.111(3) Uani 1 1 d . . .
H14A H 0.6952 0.1175 0.3007 0.166 Uiso 1 1 calc R . .
H14B H 0.6631 0.0153 0.3563 0.166 Uiso 1 1 calc R . .
H14C H 0.6740 0.1224 0.4106 0.166 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 0.0449(3) 0.02617(19) 0.0279(2) 0.0010(2) -0.0002(3) 0.0032(3)
O3 0.055(3) 0.0297(14) 0.0311(17) -0.0008(14) 0.0068(19) 0.0018(17)
N2 0.038(3) 0.0277(16) 0.0259(19) -0.0005(16) -0.003(2) 0.0007(18)
O2 0.063(3) 0.0197(12) 0.0320(17) 0.0019(12) 0.003(2) 0.0022(17)
O1 0.058(2) 0.0209(12) 0.0315(17) 0.0003(13) 0.0099(18) 0.0089(16)
C5 0.045(3) 0.032(2) 0.039(3) -0.007(3) -0.005(3) 0.007(2)
N3 0.050(3) 0.0253(17) 0.030(2) -0.0036(17) 0.006(2) 0.0045(19)
C14 0.031(2) 0.0256(17) 0.030(2) -0.003(2) -0.006(2) 0.003(2)
C17 0.035(3) 0.0235(19) 0.033(3) 0.001(2) 0.004(2) 0.005(2)
C10 0.057(4) 0.0293(18) 0.034(3) -0.007(2) 0.008(3) 0.007(2)
C16 0.035(3) 0.032(2) 0.029(3) -0.005(2) -0.008(3) 0.007(2)
C21 0.051(4) 0.029(2) 0.038(3) 0.000(2) 0.014(3) 0.002(2)
C12 0.027(2) 0.0269(17) 0.029(2) -0.0027(17) -0.004(2) -0.001(2)
C9 0.037(3) 0.0237(19) 0.038(3) -0.001(2) -0.002(3) 0.004(2)
C6 0.058(4) 0.023(2) 0.050(3) -0.001(2) -0.002(3) 0.010(2)
C8 0.036(3) 0.0230(18) 0.038(3) -0.0039(19) -0.009(3) 0.002(2)
C7 0.048(3) 0.029(2) 0.036(3) 0.003(2) 0.000(3) 0.001(2)
N1 0.074(4) 0.0303(19) 0.045(3) -0.008(2) 0.006(3) 0.013(2)
O4 0.051(3) 0.057(2) 0.060(3) -0.016(2) 0.006(2) -0.006(2)
C13 0.034(3) 0.032(2) 0.028(2) 0.0003(19) 0.000(2) 0.004(2)
C20 0.054(4) 0.024(2) 0.045(3) 0.003(2) 0.010(3) 0.004(2)
C18 0.065(4) 0.0230(19) 0.043(3) -0.002(2) 0.010(3) 0.007(3)
C2 0.077(5) 0.048(3) 0.046(4) -0.012(3) 0.019(4) 0.012(3)
N4 0.048(3) 0.0255(17) 0.037(2) -0.0010(17) 0.010(2) 0.004(2)
C3 0.092(5) 0.040(3) 0.065(4) -0.015(3) 0.014(4) 0.017(3)
C19 0.062(4) 0.028(2) 0.035(3) 0.006(2) 0.012(3) 0.008(3)
C11 0.033(3) 0.0312(19) 0.030(2) 0.0037(19) -0.006(3) 0.001(2)
C15 0.097(5) 0.030(2) 0.026(2) 0.004(2) 0.002(3) 0.010(3)
O5 0.081(3) 0.059(2) 0.077(3) -0.008(2) 0.007(3) 0.009(3)
N5 0.051(4) 0.048(3) 0.076(4) -0.033(3) 0.015(3) 0.000(3)
O6 0.045(3) 0.090(3) 0.132(5) -0.018(3) 0.031(3) -0.010(3)
C1 0.098(6) 0.122(5) 0.051(4) 0.013(4) 0.002(5) 0.029(6)
C4 0.097(7) 0.089(4) 0.146(8) 0.024(5) 0.032(6) 0.050(5)

_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 2.025(3) . ?
Zn1 N2 2.037(3) . ?
Zn1 O4 2.051(4) . ?
Zn1 N4 2.059(4) 2_574 ?
Zn1 O2 2.080(2) . ?
O3 C16 1.264(5) . ?
N2 C14 1.302(5) . ?
N2 N3 1.398(5) . ?
O2 C13 1.239(4) . ?
O1 C13 1.352(5) . ?
O1 C9 1.388(4) . ?
C5 N1 1.355(6) . ?
C5 C6 1.405(7) . ?
C5 C10 1.418(4) . ?
N3 C16 1.319(4) . ?
C14 C12 1.459(5) . ?
C14 C15 1.497(6) . ?
C17 C18 1.363(6) . ?
C17 C21 1.373(5) . ?
C17 C16 1.500(6) . ?
C10 C9 1.356(6) . ?
C10 H10 0.9300 . ?
C21 C20 1.379(6) . ?
C21 H12 0.9300 . ?
C12 C11 1.382(4) . ?
C12 C13 1.438(5) . ?
C9 C8 1.372(6) . ?
C6 C7 1.355(6) . ?
C6 H16 0.9300 . ?
C8 C11 1.404(5) . ?
C8 C7 1.420(4) . ?
C7 H18 0.9300 . ?
N1 C2 1.450(6) . ?
N1 C3 1.475(5) . ?
O4 N5 1.274(6) . ?
C20 N4 1.324(5) . ?
C20 H22 0.9300 . ?
C18 C19 1.377(6) . ?
C18 H23 0.9300 . ?
C2 C1 1.484(8) . ?
C2 H25A 0.9700 . ?
C2 H25B 0.9700 . ?
N4 C19 1.344(5) . ?
N4 Zn1 2.059(4) 2_575 ?
C3 C4 1.485(8) . ?
C3 H27A 0.9700 . ?
C3 H27B 0.9700 . ?
C19 H28 0.9300 . ?
C11 H29 0.9300 . ?
C15 H37A 0.9600 . ?
C15 H37B 0.9600 . ?
C15 H37C 0.9600 . ?
O5 N5 1.253(5) . ?
N5 O6 1.219(6) . ?
C1 H1A 0.9600 . ?
C1 H1B 0.9600 . ?
C1 H1C 0.9600 . ?
C4 H14A 0.9600 . ?
C4 H14B 0.9600 . ?
C4 H14C 0.9600 . ?

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 N2 80.07(11) . . ?
O3 Zn1 O4 99.85(13) . . ?
N2 Zn1 O4 141.23(16) . . ?
O3 Zn1 N4 94.73(14) . 2_574 ?
N2 Zn1 N4 125.61(16) . 2_574 ?
O4 Zn1 N4 93.15(15) . 2_574 ?
O3 Zn1 O2 166.04(11) . . ?
N2 Zn1 O2 85.99(12) . . ?
O4 Zn1 O2 91.45(13) . . ?
N4 Zn1 O2 92.79(13) 2_574 . ?
C16 O3 Zn1 108.4(2) . . ?
C14 N2 N3 115.4(3) . . ?
C14 N2 Zn1 132.5(3) . . ?
N3 N2 Zn1 112.0(2) . . ?
C13 O2 Zn1 128.5(3) . . ?
C13 O1 C9 123.0(3) . . ?
N1 C5 C6 122.2(4) . . ?
N1 C5 C10 121.0(5) . . ?
C6 C5 C10 116.8(5) . . ?
C16 N3 N2 110.5(4) . . ?
N2 C14 C12 121.0(4) . . ?
N2 C14 C15 121.0(4) . . ?
C12 C14 C15 118.0(3) . . ?
C18 C17 C21 117.9(4) . . ?
C18 C17 C16 122.1(3) . . ?
C21 C17 C16 120.0(4) . . ?
C9 C10 C5 119.2(5) . . ?
C9 C10 H10 120.4 . . ?
C5 C10 H10 120.4 . . ?
O3 C16 N3 128.3(4) . . ?
O3 C16 C17 118.7(3) . . ?
N3 C16 C17 113.0(4) . . ?
C17 C21 C20 119.1(4) . . ?
C17 C21 H12 120.5 . . ?
C20 C21 H12 120.5 . . ?
C11 C12 C13 116.9(4) . . ?
C11 C12 C14 119.8(4) . . ?
C13 C12 C14 123.2(3) . . ?
C10 C9 C8 124.9(4) . . ?
C10 C9 O1 116.6(4) . . ?
C8 C9 O1 118.6(4) . . ?
C7 C6 C5 122.4(4) . . ?
C7 C6 H16 118.8 . . ?
C5 C6 H16 118.8 . . ?
C9 C8 C11 119.6(3) . . ?
C9 C8 C7 116.0(4) . . ?
C11 C8 C7 124.4(4) . . ?
C6 C7 C8 120.7(5) . . ?
C6 C7 H18 119.6 . . ?
C8 C7 H18 119.6 . . ?
C5 N1 C2 122.6(4) . . ?
C5 N1 C3 121.0(5) . . ?
C2 N1 C3 116.4(4) . . ?
N5 O4 Zn1 106.2(3) . . ?
O2 C13 O1 112.9(4) . . ?
O2 C13 C12 127.4(4) . . ?
O1 C13 C12 119.6(3) . . ?
N4 C20 C21 123.6(3) . . ?
N4 C20 H22 118.2 . . ?
C21 C20 H22 118.2 . . ?
C17 C18 C19 119.9(4) . . ?
C17 C18 H23 120.1 . . ?
C19 C18 H23 120.1 . . ?
N1 C2 C1 112.3(5) . . ?
N1 C2 H25A 109.1 . . ?
C1 C2 H25A 109.1 . . ?
N1 C2 H25B 109.1 . . ?
C1 C2 H25B 109.1 . . ?
H25A C2 H25B 107.9 . . ?
C20 N4 C19 116.7(4) . . ?
C20 N4 Zn1 124.3(3) . 2_575 ?
C19 N4 Zn1 117.3(3) . 2_575 ?
N1 C3 C4 110.7(5) . . ?
N1 C3 H27A 109.5 . . ?
C4 C3 H27A 109.5 . . ?
N1 C3 H27B 109.5 . . ?
C4 C3 H27B 109.5 . . ?
H27A C3 H27B 108.1 . . ?
N4 C19 C18 122.7(4) . . ?
N4 C19 H28 118.7 . . ?
C18 C19 H28 118.7 . . ?
C12 C11 C8 122.3(4) . . ?
C12 C11 H29 118.9 . . ?
C8 C11 H29 118.9 . . ?
C14 C15 H37A 109.5 . . ?
C14 C15 H37B 109.5 . . ?
H37A C15 H37B 109.5 . . ?
C14 C15 H37C 109.5 . . ?
H37A C15 H37C 109.5 . . ?
H37B C15 H37C 109.5 . . ?
O6 N5 O5 122.6(6) . . ?
O6 N5 O4 120.4(6) . . ?
O5 N5 O4 116.9(5) . . ?
C2 C1 H1A 109.5 . . ?
C2 C1 H1B 109.5 . . ?
H1A C1 H1B 109.5 . . ?
C2 C1 H1C 109.5 . . ?
H1A C1 H1C 109.5 . . ?
H1B C1 H1C 109.5 . . ?
C3 C4 H14A 109.5 . . ?
C3 C4 H14B 109.5 . . ?
H14A C4 H14B 109.5 . . ?
C3 C4 H14C 109.5 . . ?
H14A C4 H14C 109.5 . . ?
H14B C4 H14C 109.5 . . ?

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
N2 Zn1 O3 C16 -7.5(3) . . . . ?
O4 Zn1 O3 C16 -148.1(3) . . . . ?
N4 Zn1 O3 C16 117.9(3) 2_574 . . . ?
O2 Zn1 O3 C16 -4.5(8) . . . . ?
O3 Zn1 N2 C14 -168.7(5) . . . . ?
O4 Zn1 N2 C14 -75.3(5) . . . . ?
N4 Zn1 N2 C14 102.6(4) 2_574 . . . ?
O2 Zn1 N2 C14 12.0(4) . . . . ?
O3 Zn1 N2 N3 6.4(3) . . . . ?
O4 Zn1 N2 N3 99.7(3) . . . . ?
N4 Zn1 N2 N3 -82.4(3) 2_574 . . . ?
O2 Zn1 N2 N3 -172.9(3) . . . . ?
O3 Zn1 O2 C13 -13.0(9) . . . . ?
N2 Zn1 O2 C13 -10.1(5) . . . . ?
O4 Zn1 O2 C13 131.2(5) . . . . ?
N4 Zn1 O2 C13 -135.6(5) 2_574 . . . ?
C14 N2 N3 C16 171.9(4) . . . . ?
Zn1 N2 N3 C16 -4.0(5) . . . . ?
N3 N2 C14 C12 177.8(4) . . . . ?
Zn1 N2 C14 C12 -7.3(7) . . . . ?
N3 N2 C14 C15 -2.6(6) . . . . ?
Zn1 N2 C14 C15 172.3(3) . . . . ?
N1 C5 C10 C9 -178.6(5) . . . . ?
C6 C5 C10 C9 -1.0(8) . . . . ?
Zn1 O3 C16 N3 8.7(7) . . . . ?
Zn1 O3 C16 C17 -171.0(4) . . . . ?
N2 N3 C16 O3 -3.4(8) . . . . ?
N2 N3 C16 C17 176.3(4) . . . . ?
C18 C17 C16 O3 -175.4(5) . . . . ?
C21 C17 C16 O3 5.9(7) . . . . ?
C18 C17 C16 N3 4.9(8) . . . . ?
C21 C17 C16 N3 -173.8(5) . . . . ?
C18 C17 C21 C20 -3.7(8) . . . . ?
C16 C17 C21 C20 175.0(5) . . . . ?
N2 C14 C12 C11 178.5(5) . . . . ?
C15 C14 C12 C11 -1.0(7) . . . . ?
N2 C14 C12 C13 -4.3(7) . . . . ?
C15 C14 C12 C13 176.1(5) . . . . ?
C5 C10 C9 C8 -1.7(9) . . . . ?
C5 C10 C9 O1 177.6(4) . . . . ?
C13 O1 C9 C10 177.3(5) . . . . ?
C13 O1 C9 C8 -3.3(7) . . . . ?
N1 C5 C6 C7 -179.1(5) . . . . ?
C10 C5 C6 C7 3.4(8) . . . . ?
C10 C9 C8 C11 -178.1(5) . . . . ?
O1 C9 C8 C11 2.5(8) . . . . ?
C10 C9 C8 C7 2.2(8) . . . . ?
O1 C9 C8 C7 -177.2(4) . . . . ?
C5 C6 C7 C8 -3.0(9) . . . . ?
C9 C8 C7 C6 0.2(8) . . . . ?
C11 C8 C7 C6 -179.5(5) . . . . ?
C6 C5 N1 C2 179.4(5) . . . . ?
C10 C5 N1 C2 -3.2(9) . . . . ?
C6 C5 N1 C3 -0.7(9) . . . . ?
C10 C5 N1 C3 176.7(5) . . . . ?
O3 Zn1 O4 N5 91.9(3) . . . . ?
N2 Zn1 O4 N5 5.5(4) . . . . ?
N4 Zn1 O4 N5 -172.8(3) 2_574 . . . ?
O2 Zn1 O4 N5 -79.9(3) . . . . ?
Zn1 O2 C13 O1 -172.8(3) . . . . ?
Zn1 O2 C13 C12 4.0(8) . . . . ?
C9 O1 C13 O2 179.3(4) . . . . ?
C9 O1 C13 C12 2.1(7) . . . . ?
C11 C12 C13 O2 -176.9(5) . . . . ?
C14 C12 C13 O2 5.9(9) . . . . ?
C11 C12 C13 O1 -0.2(8) . . . . ?
C14 C12 C13 O1 -177.4(4) . . . . ?
C17 C21 C20 N4 0.8(8) . . . . ?
C21 C17 C18 C19 2.9(8) . . . . ?
C16 C17 C18 C19 -175.8(5) . . . . ?
C5 N1 C2 C1 -84.6(7) . . . . ?
C3 N1 C2 C1 95.5(6) . . . . ?
C21 C20 N4 C19 2.8(8) . . . . ?
C21 C20 N4 Zn1 -161.8(4) . . . 2_575 ?
C5 N1 C3 C4 -89.9(8) . . . . ?
C2 N1 C3 C4 90.0(7) . . . . ?
C20 N4 C19 C18 -3.7(8) . . . . ?
Zn1 N4 C19 C18 162.0(4) 2_575 . . . ?
C17 C18 C19 N4 0.8(9) . . . . ?
C13 C12 C11 C8 -0.4(8) . . . . ?
C14 C12 C11 C8 176.9(4) . . . . ?
C9 C8 C11 C12 -0.8(8) . . . . ?
C7 C8 C11 C12 179.0(5) . . . . ?
Zn1 O4 N5 O6 172.6(4) . . . . ?
Zn1 O4 N5 O5 -9.8(5) . . . . ?

_diffrn_measured_fraction_theta_max 0.914
_diffrn_reflns_theta_full        25.00
_diffrn_measured_fraction_theta_full 0.998
_refine_diff_density_max         0.630
_refine_diff_density_min         -0.566
_refine_diff_density_rms         0.074
_database_code_depnum_ccdc_archive 'CCDC 873621'