# Electronic Supplementary Material (ESI) for New Journal of Chemistry.
# This journal is © The Royal Society of Chemistry and the Centre National de la Recherche Scientifique 2016

####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_3
_database_code_depnum_ccdc_archive 'CCDC 1480528'
_audit_update_record             
;
2016-05-17 deposited with the CCDC.
2016-12-07 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
 ?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C14 H6 N4 O6 V, H4 N'
_chemical_formula_sum            'C14 H10 N5 O6 V'
_chemical_formula_weight         395.21

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'
V V 0.3005 0.5294 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 21/c'
_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                   13.9268(3)
_cell_length_b                   8.7933(2)
_cell_length_c                   13.3931(3)
_cell_angle_alpha                90.00
_cell_angle_beta                 97.667(2)
_cell_angle_gamma                90.00
_cell_volume                     1625.49(6)
_cell_formula_units_Z            4
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    4518
_cell_measurement_theta_min      3.0428
_cell_measurement_theta_max      30.3103


_exptl_crystal_description       plate
_exptl_crystal_colour            green
_exptl_crystal_size_max          0.40
_exptl_crystal_size_mid          0.30
_exptl_crystal_size_min          0.05
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.615
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             800
_exptl_absorpt_coefficient_mu    0.655
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.86205
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_process_details   '(CrysAlis PRO; Agilent, 2013)'

_exptl_special_details           
;
249 frames in 5 runs of ω scans. Crystal-detector distance = 55.0 mm. 
;

_diffrn_ambient_temperature      293(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'SuperNova (Mo) X-ray Source'
_diffrn_radiation_monochromator  Mirror
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, Atlas'
_diffrn_measurement_method       'ω scans'
_diffrn_detector_area_resol_mean 10.4933
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            9720
_diffrn_reflns_av_R_equivalents  0.0240
_diffrn_reflns_av_sigmaI/netI    0.0276
_diffrn_reflns_limit_h_min       -18
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_theta_min         3.05
_diffrn_reflns_theta_max         27.48
_reflns_number_total             3722
_reflns_number_gt                3053
_reflns_threshold_expression     >2σ(I)

_computing_data_collection       'CrysAlis PRO (Agilent, 2013)'
_computing_cell_refinement       'CrysAlis PRO (Agilent, 2013)'
_computing_data_reduction        'CrysAlis PRO (Agilent, 2013)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_molecular_graphics    
'ORTEP-3 for Windows version 2.02 (Farrugia, 2008)'
_computing_publication_material  'WinGX publication routines (Farrugia, 1999)'

_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)+(0.0451P)²+0.4526P] 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         3722
_refine_ls_number_parameters     251
_refine_ls_number_restraints     4
_refine_ls_R_factor_all          0.0437
_refine_ls_R_factor_gt           0.0333
_refine_ls_wR_factor_ref         0.0932
_refine_ls_wR_factor_gt          0.0873
_refine_ls_goodness_of_fit_ref   1.044
_refine_ls_restrained_S_all      1.044
_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
V1 V 0.13842(2) 0.74129(3) 0.44323(2) 0.03212(11) Uani 1 1 d . . .
N1 N 0.17609(10) 0.53638(16) 0.55338(10) 0.0306(3) Uani 1 1 d . . .
N2 N 0.31358(13) 0.3948(2) 0.88838(12) 0.0535(5) Uani 1 1 d . . .
N3 N 0.30441(11) 0.70761(17) 0.44505(10) 0.0317(3) Uani 1 1 d . . .
N4 N 0.54501(16) 0.4540(3) 0.28324(16) 0.0716(6) Uani 1 1 d . . .
N5 N 0.02957(15) 0.5509(2) 0.15876(13) 0.0452(4) Uani 1 1 d D . .
H5C H -0.0122(17) 0.629(3) 0.149(2) 0.075(9) Uiso 1 1 d D . .
H5B H 0.0779(18) 0.561(4) 0.121(2) 0.103(11) Uiso 1 1 d D . .
H5A H 0.0568(19) 0.547(3) 0.2242(14) 0.082(9) Uiso 1 1 d D . .
H5D H 0.000(2) 0.465(2) 0.137(2) 0.086(9) Uiso 1 1 d D . .
O1 O 0.12086(10) 0.55345(15) 0.36097(8) 0.0387(3) Uani 1 1 d . . .
O2 O 0.10099(11) 0.30488(17) 0.34374(10) 0.0479(4) Uani 1 1 d . . .
O3 O 0.20178(9) 0.86664(14) 0.55629(9) 0.0370(3) Uani 1 1 d . . .
O4 O 0.33214(11) 0.95737(17) 0.65039(10) 0.0537(4) Uani 1 1 d . . .
O5 O 0.13772(10) 0.85308(17) 0.34665(9) 0.0458(3) Uani 1 1 d . . .
O6 O 0.03215(10) 0.76399(17) 0.47792(11) 0.0475(4) Uani 1 1 d . . .
C1 C 0.12432(12) 0.4159(2) 0.39546(12) 0.0339(4) Uani 1 1 d . . .
C2 C 0.16329(12) 0.4025(2) 0.50538(11) 0.0302(4) Uani 1 1 d . . .
C3 C 0.18520(15) 0.2648(2) 0.55091(14) 0.0378(4) Uani 1 1 d . . .
H3 H 0.1752 0.1746 0.5148 0.045 Uiso 1 1 calc R . .
C4 C 0.22264(15) 0.2635(2) 0.65225(14) 0.0398(4) Uani 1 1 d . . .
H4 H 0.2392 0.1724 0.6854 0.048 Uiso 1 1 calc R . .
C5 C 0.23480(13) 0.4007(2) 0.70279(12) 0.0336(4) Uani 1 1 d . . .
C6 C 0.21040(13) 0.5353(2) 0.65166(12) 0.0337(4) Uani 1 1 d . . .
H6 H 0.2181 0.6270 0.6864 0.040 Uiso 1 1 calc R . .
C7 C 0.27734(14) 0.4014(2) 0.80729(13) 0.0391(4) Uani 1 1 d . . .
C8 C 0.29452(14) 0.8827(2) 0.57985(13) 0.0353(4) Uani 1 1 d . . .
C9 C 0.35511(13) 0.7974(2) 0.51361(13) 0.0329(4) Uani 1 1 d . . .
C10 C 0.45452(14) 0.8108(2) 0.52394(15) 0.0434(5) Uani 1 1 d . . .
H10 H 0.4870 0.8749 0.5724 0.052 Uiso 1 1 calc R . .
C11 C 0.50484(15) 0.7275(3) 0.46106(16) 0.0475(5) Uani 1 1 d . . .
H11 H 0.5719 0.7351 0.4654 0.057 Uiso 1 1 calc R . .
C12 C 0.45310(13) 0.6318(2) 0.39090(13) 0.0397(4) Uani 1 1 d . . .
C13 C 0.35286(13) 0.6253(2) 0.38406(13) 0.0363(4) Uani 1 1 d . . .
H13 H 0.3186 0.5623 0.3361 0.044 Uiso 1 1 calc R . .
C14 C 0.50317(15) 0.5342(3) 0.32815(15) 0.0492(5) Uani 1 1 d . . .


_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
V1 O6 1.6216(14) . ?
V1 O5 1.6236(13) . ?
V1 O3 1.9824(12) . ?
V1 O1 1.9824(13) . ?
V1 N3 2.3275(15) . ?
V1 N1 2.3434(14) . ?
N1 C6 1.339(2) . ?
N1 C2 1.342(2) . ?
N2 C7 1.136(2) . ?
N3 C9 1.338(2) . ?
N3 C13 1.339(2) . ?
N4 C14 1.137(3) . ?
N5 H5C 0.895(17) . ?
N5 H5B 0.900(18) . ?
N5 H5A 0.908(17) . ?
N5 H5D 0.892(17) . ?
O1 C1 1.294(2) . ?
O2 C1 1.216(2) . ?
O3 C8 1.296(2) . ?
O4 C8 1.211(2) . ?
C1 C2 1.504(2) . ?
C2 C3 1.372(2) . ?
C3 C4 1.388(3) . ?
C3 H3 0.9300 . ?
C4 C5 1.382(3) . ?
C4 H4 0.9300 . ?
C5 C6 1.387(2) . ?
C5 C7 1.445(2) . ?
C6 H6 0.9300 . ?
C8 C9 1.504(3) . ?
C9 C10 1.378(3) . ?
C10 C11 1.376(3) . ?
C10 H10 0.9300 . ?
C11 C12 1.389(3) . ?
C11 H11 0.9300 . ?
C12 C13 1.388(3) . ?
C12 C14 1.444(3) . ?
C13 H13 0.9300 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
O6 V1 O5 104.18(8) . . ?
O6 V1 O3 92.46(6) . . ?
O5 V1 O3 103.10(7) . . ?
O6 V1 O1 102.25(7) . . ?
O5 V1 O1 94.27(6) . . ?
O3 V1 O1 153.78(5) . . ?
O6 V1 N3 162.91(6) . . ?
O5 V1 N3 89.19(6) . . ?
O3 V1 N3 73.89(5) . . ?
O1 V1 N3 87.05(5) . . ?
O6 V1 N1 92.89(7) . . ?
O5 V1 N1 160.75(6) . . ?
O3 V1 N1 84.68(5) . . ?
O1 V1 N1 73.13(5) . . ?
N3 V1 N1 75.93(5) . . ?
C6 N1 C2 118.16(14) . . ?
C6 N1 V1 130.15(12) . . ?
C2 N1 V1 111.63(10) . . ?
C9 N3 C13 118.34(16) . . ?
C9 N3 V1 111.37(12) . . ?
C13 N3 V1 130.00(12) . . ?
H5C N5 H5B 111(3) . . ?
H5C N5 H5A 111(3) . . ?
H5B N5 H5A 108(3) . . ?
H5C N5 H5D 109(2) . . ?
H5B N5 H5D 104(3) . . ?
H5A N5 H5D 114(3) . . ?
C1 O1 V1 125.79(10) . . ?
C8 O3 V1 125.06(11) . . ?
O2 C1 O1 123.57(15) . . ?
O2 C1 C2 121.96(17) . . ?
O1 C1 C2 114.44(14) . . ?
N1 C2 C3 123.65(14) . . ?
N1 C2 C1 114.09(14) . . ?
C3 C2 C1 122.25(15) . . ?
C2 C3 C4 118.30(16) . . ?
C2 C3 H3 120.9 . . ?
C4 C3 H3 120.9 . . ?
C5 C4 C3 118.53(16) . . ?
C5 C4 H4 120.7 . . ?
C3 C4 H4 120.7 . . ?
C4 C5 C6 119.79(15) . . ?
C4 C5 C7 119.04(16) . . ?
C6 C5 C7 121.10(16) . . ?
N1 C6 C5 121.55(16) . . ?
N1 C6 H6 119.2 . . ?
C5 C6 H6 119.2 . . ?
N2 C7 C5 176.2(2) . . ?
O4 C8 O3 124.25(18) . . ?
O4 C8 C9 120.83(17) . . ?
O3 C8 C9 114.90(15) . . ?
N3 C9 C10 123.40(18) . . ?
N3 C9 C8 114.39(16) . . ?
C10 C9 C8 122.21(16) . . ?
C11 C10 C9 118.66(18) . . ?
C11 C10 H10 120.7 . . ?
C9 C10 H10 120.7 . . ?
C10 C11 C12 118.42(19) . . ?
C10 C11 H11 120.8 . . ?
C12 C11 H11 120.8 . . ?
C13 C12 C11 119.74(18) . . ?
C13 C12 C14 119.78(18) . . ?
C11 C12 C14 120.43(18) . . ?
N3 C13 C12 121.43(17) . . ?
N3 C13 H13 119.3 . . ?
C12 C13 H13 119.3 . . ?
N4 C14 C12 176.4(2) . . ?

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
O6 V1 N1 C6 -82.95(16) . . . . ?
O5 V1 N1 C6 124.3(2) . . . . ?
O3 V1 N1 C6 9.26(15) . . . . ?
O1 V1 N1 C6 175.12(16) . . . . ?
N3 V1 N1 C6 83.95(15) . . . . ?
O6 V1 N1 C2 99.84(12) . . . . ?
O5 V1 N1 C2 -52.9(2) . . . . ?
O3 V1 N1 C2 -167.96(12) . . . . ?
O1 V1 N1 C2 -2.09(11) . . . . ?
N3 V1 N1 C2 -93.26(12) . . . . ?
O6 V1 N3 C9 -43.2(3) . . . . ?
O5 V1 N3 C9 98.73(13) . . . . ?
O3 V1 N3 C9 -5.16(11) . . . . ?
O1 V1 N3 C9 -166.95(12) . . . . ?
N1 V1 N3 C9 -93.60(12) . . . . ?
O6 V1 N3 C13 143.1(2) . . . . ?
O5 V1 N3 C13 -74.91(16) . . . . ?
O3 V1 N3 C13 -178.80(16) . . . . ?
O1 V1 N3 C13 19.41(15) . . . . ?
N1 V1 N3 C13 92.76(15) . . . . ?
O6 V1 O1 C1 -81.34(15) . . . . ?
O5 V1 O1 C1 173.14(15) . . . . ?
O3 V1 O1 C1 41.4(2) . . . . ?
N3 V1 O1 C1 84.18(14) . . . . ?
N1 V1 O1 C1 7.98(14) . . . . ?
O6 V1 O3 C8 172.21(14) . . . . ?
O5 V1 O3 C8 -82.61(14) . . . . ?
O1 V1 O3 C8 47.6(2) . . . . ?
N3 V1 O3 C8 2.66(13) . . . . ?
N1 V1 O3 C8 79.53(14) . . . . ?
V1 O1 C1 O2 170.18(14) . . . . ?
V1 O1 C1 C2 -11.9(2) . . . . ?
C6 N1 C2 C3 -1.3(3) . . . . ?
V1 N1 C2 C3 176.23(15) . . . . ?
C6 N1 C2 C1 179.87(15) . . . . ?
V1 N1 C2 C1 -2.55(17) . . . . ?
O2 C1 C2 N1 -173.56(17) . . . . ?
O1 C1 C2 N1 8.5(2) . . . . ?
O2 C1 C2 C3 7.6(3) . . . . ?
O1 C1 C2 C3 -170.34(17) . . . . ?
N1 C2 C3 C4 0.0(3) . . . . ?
C1 C2 C3 C4 178.73(17) . . . . ?
C2 C3 C4 C5 0.9(3) . . . . ?
C3 C4 C5 C6 -0.5(3) . . . . ?
C3 C4 C5 C7 -177.54(18) . . . . ?
C2 N1 C6 C5 1.7(2) . . . . ?
V1 N1 C6 C5 -175.35(13) . . . . ?
C4 C5 C6 N1 -0.8(3) . . . . ?
C7 C5 C6 N1 176.15(17) . . . . ?
V1 O3 C8 O4 -178.48(14) . . . . ?
V1 O3 C8 C9 0.1(2) . . . . ?
C13 N3 C9 C10 0.8(3) . . . . ?
V1 N3 C9 C10 -173.67(14) . . . . ?
C13 N3 C9 C8 -178.82(15) . . . . ?
V1 N3 C9 C8 6.72(18) . . . . ?
O4 C8 C9 N3 173.55(17) . . . . ?
O3 C8 C9 N3 -5.1(2) . . . . ?
O4 C8 C9 C10 -6.1(3) . . . . ?
O3 C8 C9 C10 175.30(16) . . . . ?
N3 C9 C10 C11 -0.3(3) . . . . ?
C8 C9 C10 C11 179.29(18) . . . . ?
C9 C10 C11 C12 -0.9(3) . . . . ?
C10 C11 C12 C13 1.6(3) . . . . ?
C10 C11 C12 C14 -175.64(19) . . . . ?
C9 N3 C13 C12 0.0(3) . . . . ?
V1 N3 C13 C12 173.23(13) . . . . ?
C11 C12 C13 N3 -1.2(3) . . . . ?
C14 C12 C13 N3 176.12(17) . . . . ?


loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
N5 H5C O2 0.895(17) 1.995(18) 2.877(3) 168(2) 2
N5 H5B O3 0.900(18) 2.13(2) 3.007(2) 165(3) 4_575
N5 H5B O6 0.900(18) 2.47(3) 2.922(2) 111(2) 4_575
N5 H5A O1 0.908(17) 1.929(17) 2.834(2) 175(3) .
N5 H5D O5 0.892(17) 2.19(2) 2.901(2) 136(3) 2_545
N5 H5D O6 0.892(17) 2.35(2) 3.168(2) 153(3) 2_545

_diffrn_measured_fraction_theta_max 0.998
_diffrn_reflns_theta_full        27.48
_diffrn_measured_fraction_theta_full 0.998
_refine_diff_density_max         0.242
_refine_diff_density_min         -0.311
_refine_diff_density_rms         0.047
####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_4
_database_code_depnum_ccdc_archive 'CCDC 1480529'
_audit_update_record             
;
2016-05-17 deposited with the CCDC.
2016-12-07 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
 ?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C10 H6 N4 O6 V, H4 N'
_chemical_formula_sum            'C10 H10 N5 O6 V'
_chemical_formula_weight         347.17

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'
V V 0.3005 0.5294 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'

loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   7.89910(10)
_cell_length_b                   8.15860(10)
_cell_length_c                   12.3149(2)
_cell_angle_alpha                74.5170(10)
_cell_angle_beta                 85.1740(10)
_cell_angle_gamma                64.5960(10)
_cell_volume                     690.463(17)
_cell_formula_units_Z            2
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    3045
_cell_measurement_theta_min      0.41
_cell_measurement_theta_max      27.48

_exptl_crystal_description       prism
_exptl_crystal_colour            yellow
_exptl_crystal_size_max          0.35
_exptl_crystal_size_mid          0.30
_exptl_crystal_size_min          0.13
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.670
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             352
_exptl_absorpt_coefficient_mu    0.757
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.7775
_exptl_absorpt_correction_T_max  0.9080
_exptl_absorpt_process_details   'SCALEPACK (Otwinowski & Minor, 1997)'

_exptl_special_details           
;
388 frames in 5 sets of ω scans. Rotation/frame = 1.0 °.
Crystal-detector distance = 25.00 mm. Measuring time  = 20 s/°.
;

_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  
;
Nonius KappaCCD area-detector diffractometer
;
_diffrn_measurement_method       'ω scans'
_diffrn_detector_area_resol_mean 0.055
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            5540
_diffrn_reflns_av_R_equivalents  0.0139
_diffrn_reflns_av_sigmaI/netI    0.0240
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_theta_min         4.11
_diffrn_reflns_theta_max         27.46
_reflns_number_total             3118
_reflns_number_gt                2897
_reflns_threshold_expression     >2σ(I)

_computing_data_collection       'KappaCCD Reference Manual (Nonius, 1998)'
_computing_cell_refinement       'DENZO-SMN (Otwinowski & Minor, 1997)'
_computing_data_reduction        'DENZO-SMN (Otwinowski & Minor, 1997)'
_computing_structure_solution    'SIR97 (Altomare et al., 1999)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_molecular_graphics    
'ORTEP-3 for Windows version 2.02 (Farrugia, 2008)'
_computing_publication_material  'WinGX publication routines (Farrugia, 1999)'

_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)+(0.0398P)²+0.2683P] 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         3118
_refine_ls_number_parameters     215
_refine_ls_number_restraints     4
_refine_ls_R_factor_all          0.0289
_refine_ls_R_factor_gt           0.0264
_refine_ls_wR_factor_ref         0.0758
_refine_ls_wR_factor_gt          0.0740
_refine_ls_goodness_of_fit_ref   1.037
_refine_ls_restrained_S_all      1.036
_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
V1 V 0.15623(3) 0.51860(3) 0.713834(18) 0.02257(9) Uani 1 1 d . . .
N1 N 0.47781(16) 0.35754(15) 0.72052(10) 0.0233(2) Uani 1 1 d . . .
N2 N 0.85393(18) 0.19727(18) 0.66901(12) 0.0348(3) Uani 1 1 d . . .
N3 N 0.22508(16) 0.59884(16) 0.86516(10) 0.0254(2) Uani 1 1 d . . .
N4 N 0.2722(2) 0.6493(2) 1.07375(13) 0.0457(4) Uani 1 1 d . . .
N5 N 0.18730(19) 0.13732(18) 0.51613(12) 0.0307(3) Uani 1 1 d D . .
H5A H 0.284(3) 0.023(2) 0.5243(18) 0.048(6) Uiso 1 1 d D . .
H5C H 0.094(3) 0.127(3) 0.5600(18) 0.061(7) Uiso 1 1 d D . .
H5D H 0.156(3) 0.186(3) 0.4433(14) 0.048(6) Uiso 1 1 d D . .
H5B H 0.221(4) 0.212(4) 0.543(2) 0.077(8) Uiso 1 1 d D . .
O1 O 0.25399(14) 0.70445(13) 0.62692(8) 0.0276(2) Uani 1 1 d . . .
O2 O 0.48809(17) 0.77418(15) 0.55248(12) 0.0439(3) Uani 1 1 d . . .
O3 O 0.17580(15) 0.31181(14) 0.84521(8) 0.0292(2) Uani 1 1 d . . .
O4 O 0.2341(2) 0.17139(18) 1.02812(11) 0.0543(4) Uani 1 1 d . . .
O6 O 0.15495(16) 0.41922(16) 0.61604(9) 0.0354(2) Uani 1 1 d . . .
O5 O -0.05876(14) 0.67637(15) 0.71390(9) 0.0329(2) Uani 1 1 d . . .
C1 C 0.4280(2) 0.66194(19) 0.60688(12) 0.0266(3) Uani 1 1 d . . .
C2 C 0.55938(19) 0.46017(18) 0.65519(11) 0.0236(3) Uani 1 1 d . . .
C3 C 0.7469(2) 0.3817(2) 0.63077(13) 0.0318(3) Uani 1 1 d . . .
H3 H 0.8000 0.4584 0.5869 0.038 Uiso 1 1 calc R . .
C4 C 0.7724(2) 0.0971(2) 0.73593(13) 0.0328(3) Uani 1 1 d . . .
H4 H 0.8434 -0.0307 0.7657 0.039 Uiso 1 1 calc R . .
C5 C 0.5854(2) 0.17573(19) 0.76305(12) 0.0288(3) Uani 1 1 d . . .
H5 H 0.5346 0.1008 0.8114 0.035 Uiso 1 1 calc R . .
C6 C 0.2148(2) 0.3023(2) 0.94726(12) 0.0296(3) Uani 1 1 d . . .
C7 C 0.23516(19) 0.4706(2) 0.96110(11) 0.0261(3) Uani 1 1 d . . .
C8 C 0.2596(2) 0.4955(3) 1.06504(13) 0.0370(3) Uani 1 1 d . . .
H8 H 0.2675 0.4026 1.1301 0.044 Uiso 1 1 calc R . .
C9 C 0.2575(3) 0.7781(3) 0.97793(16) 0.0442(4) Uani 1 1 d . . .
H9 H 0.2626 0.8886 0.9810 0.053 Uiso 1 1 calc R . .
C10 C 0.2348(2) 0.7544(2) 0.87329(14) 0.0347(3) Uani 1 1 d . . .
H10 H 0.2264 0.8478 0.8083 0.042 Uiso 1 1 calc R . .


_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
V1 O6 1.6243(10) . ?
V1 O5 1.6327(10) . ?
V1 O3 1.9619(10) . ?
V1 O1 2.0100(10) . ?
V1 N1 2.3021(12) . ?
V1 N3 2.3075(12) . ?
N1 C5 1.3324(17) . ?
N1 C2 1.3340(18) . ?
N2 C4 1.329(2) . ?
N2 C3 1.3410(19) . ?
N3 C10 1.3341(19) . ?
N3 C7 1.3348(18) . ?
N4 C9 1.329(3) . ?
N4 C8 1.332(2) . ?
N5 H5A 0.900(16) . ?
N5 H5C 0.894(16) . ?
N5 H5D 0.886(16) . ?
N5 H5B 0.897(17) . ?
O1 C1 1.2844(17) . ?
O2 C1 1.2267(18) . ?
O3 C6 1.2934(18) . ?
O4 C6 1.2139(19) . ?
C1 C2 1.5020(18) . ?
C2 C3 1.381(2) . ?
C3 H3 0.9300 . ?
C4 C5 1.387(2) . ?
C4 H4 0.9300 . ?
C5 H5 0.9300 . ?
C6 C7 1.503(2) . ?
C7 C8 1.390(2) . ?
C8 H8 0.9300 . ?
C9 C10 1.390(2) . ?
C9 H9 0.9300 . ?
C10 H10 0.9300 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
O6 V1 O5 104.95(6) . . ?
O6 V1 O3 98.18(5) . . ?
O5 V1 O3 104.35(5) . . ?
O6 V1 O1 99.82(5) . . ?
O5 V1 O1 94.43(5) . . ?
O3 V1 O1 149.59(4) . . ?
O6 V1 N1 86.78(5) . . ?
O5 V1 N1 164.90(5) . . ?
O3 V1 N1 82.89(4) . . ?
O1 V1 N1 73.90(4) . . ?
O6 V1 N3 166.41(5) . . ?
O5 V1 N3 88.20(5) . . ?
O3 V1 N3 74.81(4) . . ?
O1 V1 N3 82.22(4) . . ?
N1 V1 N3 80.85(4) . . ?
C5 N1 C2 117.25(12) . . ?
C5 N1 V1 129.65(10) . . ?
C2 N1 V1 112.04(9) . . ?
C4 N2 C3 116.40(13) . . ?
C10 N3 C7 117.22(13) . . ?
C10 N3 V1 131.57(10) . . ?
C7 N3 V1 110.73(9) . . ?
C9 N4 C8 116.37(14) . . ?
H5A N5 H5C 110(2) . . ?
H5A N5 H5D 107.8(19) . . ?
H5C N5 H5D 115(2) . . ?
H5A N5 H5B 110(2) . . ?
H5C N5 H5B 104(2) . . ?
H5D N5 H5B 110(2) . . ?
C1 O1 V1 123.85(8) . . ?
C6 O3 V1 124.65(9) . . ?
O2 C1 O1 124.13(13) . . ?
O2 C1 C2 120.51(13) . . ?
O1 C1 C2 115.36(12) . . ?
N1 C2 C3 121.73(12) . . ?
N1 C2 C1 114.22(12) . . ?
C3 C2 C1 123.97(13) . . ?
N2 C3 C2 121.33(14) . . ?
N2 C3 H3 119.3 . . ?
C2 C3 H3 119.3 . . ?
N2 C4 C5 122.52(13) . . ?
N2 C4 H4 118.7 . . ?
C5 C4 H4 118.7 . . ?
N1 C5 C4 120.66(13) . . ?
N1 C5 H5 119.7 . . ?
C4 C5 H5 119.7 . . ?
O4 C6 O3 124.89(14) . . ?
O4 C6 C7 120.43(14) . . ?
O3 C6 C7 114.68(12) . . ?
N3 C7 C8 121.48(14) . . ?
N3 C7 C6 114.93(12) . . ?
C8 C7 C6 123.58(14) . . ?
N4 C8 C7 121.66(15) . . ?
N4 C8 H8 119.2 . . ?
C7 C8 H8 119.2 . . ?
N4 C9 C10 122.64(16) . . ?
N4 C9 H9 118.7 . . ?
C10 C9 H9 118.7 . . ?
N3 C10 C9 120.60(15) . . ?
N3 C10 H10 119.7 . . ?
C9 C10 H10 119.7 . . ?

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
O6 V1 N1 C5 -73.46(13) . . . . ?
O5 V1 N1 C5 144.95(18) . . . . ?
O3 V1 N1 C5 25.20(12) . . . . ?
O1 V1 N1 C5 -174.65(13) . . . . ?
N3 V1 N1 C5 100.88(12) . . . . ?
O6 V1 N1 C2 94.28(10) . . . . ?
O5 V1 N1 C2 -47.3(2) . . . . ?
O3 V1 N1 C2 -167.06(10) . . . . ?
O1 V1 N1 C2 -6.91(9) . . . . ?
N3 V1 N1 C2 -91.38(9) . . . . ?
O6 V1 N3 C10 125.8(2) . . . . ?
O5 V1 N3 C10 -68.55(14) . . . . ?
O3 V1 N3 C10 -173.94(14) . . . . ?
O1 V1 N3 C10 26.17(14) . . . . ?
N1 V1 N3 C10 101.01(14) . . . . ?
O6 V1 N3 C7 -62.6(3) . . . . ?
O5 V1 N3 C7 103.11(10) . . . . ?
O3 V1 N3 C7 -2.28(9) . . . . ?
O1 V1 N3 C7 -162.17(10) . . . . ?
N1 V1 N3 C7 -87.33(9) . . . . ?
O6 V1 O1 C1 -79.47(12) . . . . ?
O5 V1 O1 C1 174.51(11) . . . . ?
O3 V1 O1 C1 45.98(15) . . . . ?
N1 V1 O1 C1 4.26(11) . . . . ?
N3 V1 O1 C1 86.93(11) . . . . ?
O6 V1 O3 C6 167.46(12) . . . . ?
O5 V1 O3 C6 -84.74(12) . . . . ?
O1 V1 O3 C6 41.65(16) . . . . ?
N1 V1 O3 C6 81.76(12) . . . . ?
N3 V1 O3 C6 -0.65(11) . . . . ?
V1 O1 C1 O2 178.88(12) . . . . ?
V1 O1 C1 C2 -1.12(17) . . . . ?
C5 N1 C2 C3 1.0(2) . . . . ?
V1 N1 C2 C3 -168.41(11) . . . . ?
C5 N1 C2 C1 177.83(12) . . . . ?
V1 N1 C2 C1 8.43(14) . . . . ?
O2 C1 C2 N1 174.43(14) . . . . ?
O1 C1 C2 N1 -5.57(18) . . . . ?
O2 C1 C2 C3 -8.8(2) . . . . ?
O1 C1 C2 C3 171.18(13) . . . . ?
C4 N2 C3 C2 -3.4(2) . . . . ?
N1 C2 C3 N2 2.1(2) . . . . ?
C1 C2 C3 N2 -174.43(14) . . . . ?
C3 N2 C4 C5 1.8(2) . . . . ?
C2 N1 C5 C4 -2.6(2) . . . . ?
V1 N1 C5 C4 164.63(11) . . . . ?
N2 C4 C5 N1 1.2(2) . . . . ?
V1 O3 C6 O4 -177.04(14) . . . . ?
V1 O3 C6 C7 3.20(18) . . . . ?
C10 N3 C7 C8 -1.6(2) . . . . ?
V1 N3 C7 C8 -174.60(11) . . . . ?
C10 N3 C7 C6 177.39(13) . . . . ?
V1 N3 C7 C6 4.40(14) . . . . ?
O4 C6 C7 N3 175.11(15) . . . . ?
O3 C6 C7 N3 -5.12(19) . . . . ?
O4 C6 C7 C8 -5.9(2) . . . . ?
O3 C6 C7 C8 173.85(14) . . . . ?
C9 N4 C8 C7 0.9(3) . . . . ?
N3 C7 C8 N4 0.7(2) . . . . ?
C6 C7 C8 N4 -178.20(15) . . . . ?
C8 N4 C9 C10 -1.5(3) . . . . ?
C7 N3 C10 C9 1.0(2) . . . . ?
V1 N3 C10 C9 172.19(12) . . . . ?
N4 C9 C10 N3 0.6(3) . . . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
N5 H5A O2 0.900(16) 1.940(16) 2.8380(17) 176(2) 1_545
N5 H5C N2 0.894(16) 2.188(18) 3.0448(19) 160(2) 1_455
N5 H5D O5 0.886(16) 1.987(16) 2.8682(18) 172(2) 2_566
N5 H5B O6 0.897(17) 1.98(2) 2.7969(17) 150(3) .

_diffrn_measured_fraction_theta_max 0.987
_diffrn_reflns_theta_full        27.46
_diffrn_measured_fraction_theta_full 0.987
_refine_diff_density_max         0.260
_refine_diff_density_min         -0.316
_refine_diff_density_rms         0.044
####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_5
_database_code_depnum_ccdc_archive 'CCDC 1480530'
_audit_update_record             
;
2016-05-17 deposited with the CCDC.
2016-12-07 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
 ?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C10 H8 N6 O6 V, H2 O, H4 N'
_chemical_formula_sum            'C10 H14 N7 O7 V'
_chemical_formula_weight         395.22

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'
V V 0.3005 0.5294 '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                   9.2182(2)
_cell_length_b                   11.9215(3)
_cell_length_c                   14.0719(3)
_cell_angle_alpha                90.00
_cell_angle_beta                 98.587(2)
_cell_angle_gamma                90.00
_cell_volume                     1529.09(6)
_cell_formula_units_Z            4
_cell_measurement_temperature    150(2)
_cell_measurement_reflns_used    6068
_cell_measurement_theta_min      3.0073
_cell_measurement_theta_max      30.2891

_exptl_crystal_description       prism
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.60
_exptl_crystal_size_mid          0.50
_exptl_crystal_size_min          0.40
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.717
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             808
_exptl_absorpt_coefficient_mu    0.703
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.85438
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_process_details   '(CrysAlis PRO; Agilent, 2013)'

_exptl_special_details           
;
285 frames in 4 runs of ω scans. Crystal-detector distance = 55.0 mm. 
;

_diffrn_ambient_temperature      150(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'SuperNova (Mo) X-ray Source'
_diffrn_radiation_monochromator  Mirror
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, Atlas'
_diffrn_measurement_method       'ω scans'
_diffrn_detector_area_resol_mean 10.4933
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            10701
_diffrn_reflns_av_R_equivalents  0.0289
_diffrn_reflns_av_sigmaI/netI    0.0317
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_theta_min         3.01
_diffrn_reflns_theta_max         27.48
_reflns_number_total             3493
_reflns_number_gt                3103
_reflns_threshold_expression     >2σ(I)

_computing_data_collection       'CrysAlis PRO (Agilent, 2013)'
_computing_cell_refinement       'CrysAlis PRO (Agilent, 2013)'
_computing_data_reduction        'CrysAlis PRO (Agilent, 2013)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_molecular_graphics    
'ORTEP-3 for Windows version 2.02 (Farrugia, 2008)'
_computing_publication_material  'WinGX publication routines (Farrugia, 1999)'

_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)+(0.0423P)²+0.8488P] 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         3493
_refine_ls_number_parameters     244
_refine_ls_number_restraints     6
_refine_ls_R_factor_all          0.0375
_refine_ls_R_factor_gt           0.0322
_refine_ls_wR_factor_ref         0.0885
_refine_ls_wR_factor_gt          0.0849
_refine_ls_goodness_of_fit_ref   1.075
_refine_ls_restrained_S_all      1.074
_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
V1 V 0.65193(3) 0.71703(2) 0.93098(2) 0.01295(10) Uani 1 1 d . . .
N1 N 0.76367(15) 0.88918(12) 0.93893(10) 0.0135(3) Uani 1 1 d . . .
N2 N 0.85846(17) 1.10993(12) 0.96189(11) 0.0178(3) Uani 1 1 d . . .
N3 N 0.73631(18) 1.13118(13) 1.09221(12) 0.0224(3) Uani 1 1 d . . .
H3A H 0.7699 1.2003 1.0984 0.034 Uiso 1 1 calc R . .
H3B H 0.6799 1.1052 1.1324 0.034 Uiso 1 1 calc R . .
N4 N 0.87881(16) 0.68372(12) 1.01836(10) 0.0137(3) Uani 1 1 d . . .
N5 N 1.16083(16) 0.61827(12) 1.09625(11) 0.0171(3) Uani 1 1 d . . .
N6 N 1.22065(17) 0.59361(13) 0.94362(11) 0.0192(3) Uani 1 1 d . . .
H6A H 1.3107 0.5765 0.9697 0.029 Uiso 1 1 calc R . .
H6B H 1.1967 0.5938 0.8807 0.029 Uiso 1 1 calc R . .
N7 N 0.52041(18) 0.37193(14) 0.83104(12) 0.0193(3) Uani 1 1 d D . .
O1 O 0.60128(14) 0.78976(10) 1.04845(9) 0.0161(3) Uani 1 1 d . . .
O2 O 0.56305(15) 0.94794(11) 1.12624(9) 0.0224(3) Uani 1 1 d . . .
O3 O 0.78024(13) 0.68365(11) 0.83518(9) 0.0172(3) Uani 1 1 d . . .
O4 O 0.99567(15) 0.63059(13) 0.79668(9) 0.0267(3) Uani 1 1 d . . .
O5 O 0.59947(14) 0.59326(10) 0.96041(9) 0.0194(3) Uani 1 1 d . . .
O6 O 0.51819(14) 0.76486(10) 0.84973(9) 0.0171(3) Uani 1 1 d . . .
O7 O 0.37593(15) 0.57246(12) 0.76685(10) 0.0229(3) Uani 1 1 d D . .
C1 C 0.62214(19) 0.89663(14) 1.06705(12) 0.0152(3) Uani 1 1 d . . .
C2 C 0.72349(18) 0.95274(14) 1.00898(12) 0.0137(3) Uani 1 1 d . . .
C3 C 0.77140(19) 1.06503(14) 1.02115(12) 0.0156(3) Uani 1 1 d . . .
C4 C 0.8948(2) 1.04470(15) 0.89304(13) 0.0175(4) Uani 1 1 d . . .
H4 H 0.9549 1.0751 0.8501 0.021 Uiso 1 1 calc R . .
C5 C 0.84911(19) 0.93364(15) 0.88064(12) 0.0162(3) Uani 1 1 d . . .
H5 H 0.8789 0.8897 0.8306 0.019 Uiso 1 1 calc R . .
C6 C 0.91662(19) 0.65330(14) 0.85652(12) 0.0162(4) Uani 1 1 d . . .
C7 C 0.97426(19) 0.65142(13) 0.96143(12) 0.0132(3) Uani 1 1 d . . .
C8 C 1.11922(19) 0.61964(14) 1.00010(13) 0.0151(3) Uani 1 1 d . . .
C9 C 1.0628(2) 0.65194(15) 1.15086(13) 0.0185(4) Uani 1 1 d . . .
H9 H 1.0908 0.6528 1.2186 0.022 Uiso 1 1 calc R . .
C10 C 0.92172(19) 0.68584(15) 1.11333(12) 0.0161(3) Uani 1 1 d . . .
H10 H 0.8560 0.7104 1.1550 0.019 Uiso 1 1 calc R . .
H71N H 0.507(2) 0.3388(17) 0.7753(10) 0.024 Uiso 1 1 d D . .
H73N H 0.6149(12) 0.3830(18) 0.8500(16) 0.024 Uiso 1 1 d D . .
H72N H 0.480(2) 0.4380(11) 0.8248(16) 0.024 Uiso 1 1 d D . .
H74N H 0.487(2) 0.3254(15) 0.8718(13) 0.024 Uiso 1 1 d D . .
H75O H 0.411(2) 0.6298(13) 0.7959(15) 0.024 Uiso 1 1 d D . .
H76O H 0.418(2) 0.5754(19) 0.7181(11) 0.024 Uiso 1 1 d D . .


_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
V1 O5 1.6255(12) . ?
V1 O6 1.6528(13) . ?
V1 O3 1.9624(12) . ?
V1 O1 1.9831(12) . ?
V1 N1 2.2914(14) . ?
V1 N4 2.2969(15) . ?
N1 C5 1.329(2) . ?
N1 C2 1.339(2) . ?
N2 C4 1.324(2) . ?
N2 C3 1.351(2) . ?
N3 C3 1.350(2) . ?
N3 H3A 0.8800 . ?
N3 H3B 0.8800 . ?
N4 C7 1.332(2) . ?
N4 C10 1.336(2) . ?
N5 C9 1.332(2) . ?
N5 C8 1.350(2) . ?
N6 C8 1.351(2) . ?
N6 H6A 0.8800 . ?
N6 H6B 0.8800 . ?
N7 H71N 0.871(10) . ?
N7 H73N 0.882(10) . ?
N7 H72N 0.872(10) . ?
N7 H74N 0.886(10) . ?
O1 C1 1.309(2) . ?
O2 C1 1.225(2) . ?
O3 C6 1.300(2) . ?
O4 C6 1.223(2) . ?
O7 H75O 0.836(10) . ?
O7 H76O 0.839(10) . ?
C1 C2 1.489(2) . ?
C2 C3 1.412(2) . ?
C4 C5 1.393(3) . ?
C4 H4 0.9500 . ?
C5 H5 0.9500 . ?
C6 C7 1.493(2) . ?
C7 C8 1.417(2) . ?
C9 C10 1.389(3) . ?
C9 H9 0.9500 . ?
C10 H10 0.9500 . ?

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
O5 V1 O6 105.65(7) . . ?
O5 V1 O3 102.93(6) . . ?
O6 V1 O3 93.36(6) . . ?
O5 V1 O1 93.92(6) . . ?
O6 V1 O1 100.47(6) . . ?
O3 V1 O1 154.47(5) . . ?
O5 V1 N1 161.66(6) . . ?
O6 V1 N1 90.47(6) . . ?
O3 V1 N1 84.40(5) . . ?
O1 V1 N1 74.21(5) . . ?
O5 V1 N4 89.34(6) . . ?
O6 V1 N4 162.85(6) . . ?
O3 V1 N4 74.85(5) . . ?
O1 V1 N4 86.46(5) . . ?
N1 V1 N4 76.23(5) . . ?
C5 N1 C2 118.89(15) . . ?
C5 N1 V1 129.08(12) . . ?
C2 N1 V1 111.79(11) . . ?
C4 N2 C3 117.23(15) . . ?
C3 N3 H3A 120.0 . . ?
C3 N3 H3B 120.0 . . ?
H3A N3 H3B 120.0 . . ?
C7 N4 C10 118.91(15) . . ?
C7 N4 V1 111.01(11) . . ?
C10 N4 V1 129.95(12) . . ?
C9 N5 C8 117.30(15) . . ?
C8 N6 H6A 120.0 . . ?
C8 N6 H6B 120.0 . . ?
H6A N6 H6B 120.0 . . ?
H71N N7 H73N 110(2) . . ?
H71N N7 H72N 109(2) . . ?
H73N N7 H72N 107(2) . . ?
H71N N7 H74N 106(2) . . ?
H73N N7 H74N 109(2) . . ?
H72N N7 H74N 116(2) . . ?
C1 O1 V1 123.11(11) . . ?
C6 O3 V1 124.01(11) . . ?
H75O O7 H76O 100(2) . . ?
O2 C1 O1 123.72(16) . . ?
O2 C1 C2 121.88(16) . . ?
O1 C1 C2 114.40(14) . . ?
N1 C2 C3 120.67(15) . . ?
N1 C2 C1 114.52(15) . . ?
C3 C2 C1 124.75(15) . . ?
N3 C3 N2 117.10(16) . . ?
N3 C3 C2 122.58(16) . . ?
N2 C3 C2 120.30(16) . . ?
N2 C4 C5 123.04(16) . . ?
N2 C4 H4 118.5 . . ?
C5 C4 H4 118.5 . . ?
N1 C5 C4 119.86(16) . . ?
N1 C5 H5 120.1 . . ?
C4 C5 H5 120.1 . . ?
O4 C6 O3 123.90(16) . . ?
O4 C6 C7 121.12(16) . . ?
O3 C6 C7 114.95(14) . . ?
N4 C7 C8 121.06(15) . . ?
N4 C7 C6 114.89(15) . . ?
C8 C7 C6 124.04(15) . . ?
N6 C8 N5 117.96(16) . . ?
N6 C8 C7 122.10(16) . . ?
N5 C8 C7 119.91(16) . . ?
N5 C9 C10 123.06(16) . . ?
N5 C9 H9 118.5 . . ?
C10 C9 H9 118.5 . . ?
N4 C10 C9 119.70(16) . . ?
N4 C10 H10 120.2 . . ?
C9 C10 H10 120.2 . . ?

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
O5 V1 N1 C5 127.0(2) . . . . ?
O6 V1 N1 C5 -81.09(15) . . . . ?
O3 V1 N1 C5 12.23(15) . . . . ?
O1 V1 N1 C5 178.16(16) . . . . ?
N4 V1 N1 C5 87.97(15) . . . . ?
O5 V1 N1 C2 -58.7(2) . . . . ?
O6 V1 N1 C2 93.16(12) . . . . ?
O3 V1 N1 C2 -173.51(12) . . . . ?
O1 V1 N1 C2 -7.59(11) . . . . ?
N4 V1 N1 C2 -97.77(12) . . . . ?
O5 V1 N4 C7 98.83(12) . . . . ?
O6 V1 N4 C7 -52.5(2) . . . . ?
O3 V1 N4 C7 -4.75(11) . . . . ?
O1 V1 N4 C7 -167.19(11) . . . . ?
N1 V1 N4 C7 -92.60(11) . . . . ?
O5 V1 N4 C10 -76.78(15) . . . . ?
O6 V1 N4 C10 131.8(2) . . . . ?
O3 V1 N4 C10 179.63(16) . . . . ?
O1 V1 N4 C10 17.19(15) . . . . ?
N1 V1 N4 C10 91.79(15) . . . . ?
O5 V1 O1 C1 179.11(13) . . . . ?
O6 V1 O1 C1 -74.17(14) . . . . ?
O3 V1 O1 C1 47.5(2) . . . . ?
N1 V1 O1 C1 13.33(12) . . . . ?
N4 V1 O1 C1 90.01(13) . . . . ?
O5 V1 O3 C6 -81.29(14) . . . . ?
O6 V1 O3 C6 171.80(14) . . . . ?
O1 V1 O3 C6 48.8(2) . . . . ?
N1 V1 O3 C6 81.66(13) . . . . ?
N4 V1 O3 C6 4.44(13) . . . . ?
V1 O1 C1 O2 162.91(14) . . . . ?
V1 O1 C1 C2 -16.3(2) . . . . ?
C5 N1 C2 C3 -0.3(2) . . . . ?
V1 N1 C2 C3 -175.17(13) . . . . ?
C5 N1 C2 C1 177.19(15) . . . . ?
V1 N1 C2 C1 2.28(18) . . . . ?
O2 C1 C2 N1 -171.60(16) . . . . ?
O1 C1 C2 N1 7.7(2) . . . . ?
O2 C1 C2 C3 5.7(3) . . . . ?
O1 C1 C2 C3 -175.00(16) . . . . ?
C4 N2 C3 N3 179.01(16) . . . . ?
C4 N2 C3 C2 0.4(2) . . . . ?
N1 C2 C3 N3 -178.40(16) . . . . ?
C1 C2 C3 N3 4.4(3) . . . . ?
N1 C2 C3 N2 0.1(3) . . . . ?
C1 C2 C3 N2 -177.03(16) . . . . ?
C3 N2 C4 C5 -0.8(3) . . . . ?
C2 N1 C5 C4 -0.1(2) . . . . ?
V1 N1 C5 C4 173.76(12) . . . . ?
N2 C4 C5 N1 0.7(3) . . . . ?
V1 O3 C6 O4 178.64(14) . . . . ?
V1 O3 C6 C7 -3.4(2) . . . . ?
C10 N4 C7 C8 0.0(2) . . . . ?
V1 N4 C7 C8 -176.16(12) . . . . ?
C10 N4 C7 C6 -179.23(15) . . . . ?
V1 N4 C7 C6 4.61(17) . . . . ?
O4 C6 C7 N4 176.52(16) . . . . ?
O3 C6 C7 N4 -1.5(2) . . . . ?
O4 C6 C7 C8 -2.7(3) . . . . ?
O3 C6 C7 C8 179.25(15) . . . . ?
C9 N5 C8 N6 175.25(15) . . . . ?
C9 N5 C8 C7 -2.7(2) . . . . ?
N4 C7 C8 N6 -175.62(15) . . . . ?
C6 C7 C8 N6 3.5(3) . . . . ?
N4 C7 C8 N5 2.2(2) . . . . ?
C6 C7 C8 N5 -178.63(15) . . . . ?
C8 N5 C9 C10 1.1(3) . . . . ?
C7 N4 C10 C9 -1.6(2) . . . . ?
V1 N4 C10 C9 173.74(12) . . . . ?
N5 C9 C10 N4 1.1(3) . . . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
N3 H3A N6 0.88 2.53 3.352(2) 155.5 3_777
N3 H3B O2 0.88 2.16 2.789(2) 128.3 .
N3 H3B O6 0.88 2.44 2.877(2) 111.5 3_677
N6 H6A O5 0.88 2.35 2.978(2) 128.9 3_767
N6 H6B O4 0.88 2.09 2.737(2) 129.6 .
N6 H6B O7 0.88 2.48 3.060(2) 124.0 1_655
N7 H71N O6 0.871(10) 1.950(10) 2.821(2) 178(2) 2_646
N7 H73N N5 0.882(10) 2.093(11) 2.966(2) 170(2) 3_767
N7 H72N O7 0.872(10) 1.979(12) 2.819(2) 161(2) .
O7 H75O O6 0.836(10) 1.980(10) 2.8079(18) 171(2) .
N7 H74N O1 0.886(10) 2.019(10) 2.901(2) 174(2) 3_667
O7 H76O O2 0.839(10) 2.011(12) 2.8229(18) 163(2) 4_575

_diffrn_measured_fraction_theta_max 0.999
_diffrn_reflns_theta_full        27.48
_diffrn_measured_fraction_theta_full 0.999
_refine_diff_density_max         0.352
_refine_diff_density_min         -0.448
_refine_diff_density_rms         0.072
####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_6
_database_code_depnum_ccdc_archive 'CCDC 1480531'
_audit_update_record             
;
2016-05-17 deposited with the CCDC.
2016-12-07 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
 ?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C14 H10 N4 O6 Zn'
_chemical_formula_sum            'C14 H10 N4 O6 Zn'
_chemical_formula_weight         395.63

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           triclinic
_symmetry_space_group_name_H-M   P-1
_symmetry_space_group_name_Hall  '-P 1'

loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   5.0190(4)
_cell_length_b                   6.4793(4)
_cell_length_c                   12.6014(6)
_cell_angle_alpha                91.545(4)
_cell_angle_beta                 99.276(5)
_cell_angle_gamma                110.230(6)
_cell_volume                     377.97(4)
_cell_formula_units_Z            1
_cell_measurement_temperature    150(2)
_cell_measurement_reflns_used    1660
_cell_measurement_theta_min      3.2827
_cell_measurement_theta_max      30.1904

_exptl_crystal_description       plate
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.12
_exptl_crystal_size_mid          0.12
_exptl_crystal_size_min          0.04
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.738
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             200
_exptl_absorpt_coefficient_mu    1.667
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.8250
_exptl_absorpt_correction_T_max  0.9363
_exptl_absorpt_process_details   '(CrysAlis PRO; Agilent, 2013)'

_exptl_special_details           
;
369 frames in 4 runs of ω scans. Crystal-detector distance = 55.0 mm. 
;

_diffrn_ambient_temperature      150(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'SuperNova (Mo) X-ray Source'
_diffrn_radiation_monochromator  Mirror
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, Atlas'
_diffrn_measurement_method       'ω scans'
_diffrn_detector_area_resol_mean 10.4933
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            3548
_diffrn_reflns_av_R_equivalents  0.0337
_diffrn_reflns_av_sigmaI/netI    0.0542
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_theta_min         3.29
_diffrn_reflns_theta_max         27.48
_reflns_number_total             1742
_reflns_number_gt                1600
_reflns_threshold_expression     >2σ(I)

_computing_data_collection       'CrysAlis PRO (Agilent, 2013)'
_computing_cell_refinement       'CrysAlis PRO (Agilent, 2013)'
_computing_data_reduction        'CrysAlis PRO (Agilent, 2013)'
_computing_structure_solution    'SIR97 (Altomare et al., 1999)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_molecular_graphics    
'ORTEP-3 for Windows version 2.02 (Farrugia, 2008)'
_computing_publication_material  'WinGX publication routines (Farrugia, 1999)'

_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)+(0.0134P)²+0.1545P] 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         1742
_refine_ls_number_parameters     123
_refine_ls_number_restraints     2
_refine_ls_R_factor_all          0.0430
_refine_ls_R_factor_gt           0.0365
_refine_ls_wR_factor_ref         0.0706
_refine_ls_wR_factor_gt          0.0667
_refine_ls_goodness_of_fit_ref   1.151
_refine_ls_restrained_S_all      1.152
_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 0.5000 0.5000 0.5000 0.01650(13) Uani 1 2 d S . .
N1 N 0.4284(4) 0.4547(3) 0.66127(15) 0.0149(4) Uani 1 1 d . . .
N2 N 0.0595(6) 0.7386(4) 0.93236(19) 0.0354(6) Uani 1 1 d . . .
O1 O 0.6846(3) 0.2624(3) 0.54062(12) 0.0168(4) Uani 1 1 d . . .
O2 O 0.7541(4) 0.0495(3) 0.67138(13) 0.0211(4) Uani 1 1 d . . .
O3 O 0.1044(4) 0.2462(3) 0.43522(14) 0.0197(4) Uani 1 1 d D . .
C1 C 0.6600(5) 0.1899(4) 0.63254(18) 0.0155(5) Uani 1 1 d . . .
C2 C 0.5089(5) 0.2914(4) 0.70318(18) 0.0159(5) Uani 1 1 d . . .
C3 C 0.4642(5) 0.2234(4) 0.80374(19) 0.0191(5) Uani 1 1 d . . .
H3 H 0.5201 0.1057 0.8300 0.023 Uiso 1 1 calc R . .
C4 C 0.3376(5) 0.3279(4) 0.86590(19) 0.0214(5) Uani 1 1 d . . .
H4 H 0.3001 0.2817 0.9346 0.026 Uiso 1 1 calc R . .
C5 C 0.2662(5) 0.5036(4) 0.82448(19) 0.0171(5) Uani 1 1 d . . .
C6 C 0.3141(5) 0.5610(4) 0.72199(18) 0.0171(5) Uani 1 1 d . . .
H6 H 0.2636 0.6801 0.6942 0.020 Uiso 1 1 calc R . .
C7 C 0.1486(6) 0.6315(4) 0.8858(2) 0.0226(6) Uani 1 1 d . . .
H3B H 0.145(7) 0.143(4) 0.415(3) 0.057(11) Uiso 1 1 d D . .
H3A H -0.030(5) 0.216(5) 0.470(2) 0.044(10) Uiso 1 1 d D . .


_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 2.0895(15) 2_666 ?
Zn1 O1 2.0895(15) . ?
Zn1 O3 2.1118(18) 2_666 ?
Zn1 O3 2.1118(18) . ?
Zn1 N1 2.1306(19) 2_666 ?
Zn1 N1 2.1306(19) . ?
N1 C6 1.332(3) . ?
N1 C2 1.349(3) . ?
N2 C7 1.141(3) . ?
O1 C1 1.270(3) . ?
O2 C1 1.240(3) . ?
O3 H3B 0.807(18) . ?
O3 H3A 0.831(18) . ?
C1 C2 1.527(3) . ?
C2 C3 1.380(3) . ?
C3 C4 1.380(3) . ?
C3 H3 0.9500 . ?
C4 C5 1.397(3) . ?
C4 H4 0.9500 . ?
C5 C6 1.389(3) . ?
C5 C7 1.444(3) . ?
C6 H6 0.9500 . ?

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 O1 180.00(8) 2_666 . ?
O1 Zn1 O3 89.77(7) 2_666 2_666 ?
O1 Zn1 O3 90.23(7) . 2_666 ?
O1 Zn1 O3 90.23(7) 2_666 . ?
O1 Zn1 O3 89.77(7) . . ?
O3 Zn1 O3 180.0 2_666 . ?
O1 Zn1 N1 78.65(7) 2_666 2_666 ?
O1 Zn1 N1 101.35(7) . 2_666 ?
O3 Zn1 N1 92.32(7) 2_666 2_666 ?
O3 Zn1 N1 87.68(7) . 2_666 ?
O1 Zn1 N1 101.35(7) 2_666 . ?
O1 Zn1 N1 78.65(7) . . ?
O3 Zn1 N1 87.68(7) 2_666 . ?
O3 Zn1 N1 92.32(7) . . ?
N1 Zn1 N1 180.000(1) 2_666 . ?
C6 N1 C2 118.3(2) . . ?
C6 N1 Zn1 129.01(15) . . ?
C2 N1 Zn1 112.69(15) . . ?
C1 O1 Zn1 116.36(14) . . ?
Zn1 O3 H3B 106(3) . . ?
Zn1 O3 H3A 119(2) . . ?
H3B O3 H3A 116(3) . . ?
O2 C1 O1 126.2(2) . . ?
O2 C1 C2 117.1(2) . . ?
O1 C1 C2 116.69(19) . . ?
N1 C2 C3 122.6(2) . . ?
N1 C2 C1 115.3(2) . . ?
C3 C2 C1 122.1(2) . . ?
C2 C3 C4 119.5(2) . . ?
C2 C3 H3 120.2 . . ?
C4 C3 H3 120.2 . . ?
C3 C4 C5 117.8(2) . . ?
C3 C4 H4 121.1 . . ?
C5 C4 H4 121.1 . . ?
C6 C5 C4 119.5(2) . . ?
C6 C5 C7 118.5(2) . . ?
C4 C5 C7 122.0(2) . . ?
N1 C6 C5 122.2(2) . . ?
N1 C6 H6 118.9 . . ?
C5 C6 H6 118.9 . . ?
N2 C7 C5 177.7(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 N1 C6 -4.0(2) 2_666 . . . ?
O1 Zn1 N1 C6 176.0(2) . . . . ?
O3 Zn1 N1 C6 85.3(2) 2_666 . . . ?
O3 Zn1 N1 C6 -94.7(2) . . . . ?
O1 Zn1 N1 C2 174.64(15) 2_666 . . . ?
O1 Zn1 N1 C2 -5.36(15) . . . . ?
O3 Zn1 N1 C2 -96.06(16) 2_666 . . . ?
O3 Zn1 N1 C2 83.94(16) . . . . ?
O3 Zn1 O1 C1 91.68(16) 2_666 . . . ?
O3 Zn1 O1 C1 -88.32(16) . . . . ?
N1 Zn1 O1 C1 -175.91(16) 2_666 . . . ?
N1 Zn1 O1 C1 4.09(16) . . . . ?
Zn1 O1 C1 O2 -179.96(18) . . . . ?
Zn1 O1 C1 C2 -2.2(3) . . . . ?
C6 N1 C2 C3 3.3(3) . . . . ?
Zn1 N1 C2 C3 -175.52(19) . . . . ?
C6 N1 C2 C1 -175.30(19) . . . . ?
Zn1 N1 C2 C1 5.9(2) . . . . ?
O2 C1 C2 N1 175.3(2) . . . . ?
O1 C1 C2 N1 -2.6(3) . . . . ?
O2 C1 C2 C3 -3.3(3) . . . . ?
O1 C1 C2 C3 178.7(2) . . . . ?
N1 C2 C3 C4 -1.3(4) . . . . ?
C1 C2 C3 C4 177.2(2) . . . . ?
C2 C3 C4 C5 -1.6(4) . . . . ?
C3 C4 C5 C6 2.4(4) . . . . ?
C3 C4 C5 C7 -176.4(2) . . . . ?
C2 N1 C6 C5 -2.4(3) . . . . ?
Zn1 N1 C6 C5 176.23(17) . . . . ?
C4 C5 C6 N1 -0.5(4) . . . . ?
C7 C5 C6 N1 178.4(2) . . . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
O3 H3B O2 0.807(18) 1.88(2) 2.663(2) 162(4) 2_656
O3 H3A O1 0.831(18) 1.91(2) 2.695(2) 158(3) 1_455

_diffrn_measured_fraction_theta_max 0.998
_diffrn_reflns_theta_full        27.48
_diffrn_measured_fraction_theta_full 0.998
_refine_diff_density_max         0.429
_refine_diff_density_min         -0.346
_refine_diff_density_rms         0.087
####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_7
_database_code_depnum_ccdc_archive 'CCDC 1480532'
_audit_update_record             
;
2016-05-17 deposited with the CCDC.
2016-12-07 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014
_chemical_name_systematic        
;
 ?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C24 H18 N8 O4 Zn, C7 H8'
_chemical_formula_sum            'C31 H26 N8 O4 Zn'
_chemical_formula_weight         639.97

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'

_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;

loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   10.5093(2)
_cell_length_b                   11.7016(2)
_cell_length_c                   12.5825(2)
_cell_angle_alpha                81.1590(10)
_cell_angle_beta                 86.7830(10)
_cell_angle_gamma                72.6540(10)
_cell_volume                     1459.34(4)
_cell_formula_units_Z            2
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    6575
_cell_measurement_theta_min      0.41
_cell_measurement_theta_max      27.48

_exptl_crystal_description       prism
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_density_diffrn    1.456
_exptl_crystal_F_000             660
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.380
_exptl_crystal_size_mid          0.250
_exptl_crystal_size_min          0.250
_exptl_absorpt_coefficient_mu    0.893
_shelx_estimated_absorpt_T_min   0.728
_shelx_estimated_absorpt_T_max   0.807
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.7281
_exptl_absorpt_correction_T_max  0.8078
_exptl_absorpt_process_details   'SCALEPACK (Otwinowski & Minor, 1997)'

_exptl_special_details           
;
424 frames in 5 sets of ω scans. Rotation/frame = 1.0 °.
Crystal-detector distance = 25.00 mm. Measuring time  = 120 s/°.
;

_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  
;
Nonius KappaCCD area-detector diffractometer
;
_diffrn_measurement_method       'ω scans'
_diffrn_detector_area_resol_mean 0.055
_diffrn_reflns_number            12042
_diffrn_reflns_av_unetI/netI     0.0221
_diffrn_reflns_av_R_equivalents  0.0122
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_theta_min         3.687
_diffrn_reflns_theta_max         27.460
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.990
_diffrn_measured_fraction_theta_full 0.988
_diffrn_reflns_Laue_measured_fraction_max 0.990
_diffrn_reflns_Laue_measured_fraction_full 0.988
_diffrn_reflns_point_group_measured_fraction_max 0.990
_diffrn_reflns_point_group_measured_fraction_full 0.988
_reflns_number_total             6609
_reflns_number_gt                5893
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;

_computing_data_collection       'KappaCCD Reference Manual (Nonius, 1998)'
_computing_cell_refinement       'DENZO-SMN (Otwinowski & Minor, 1997)'
_computing_data_reduction        'DENZO-SMN (Otwinowski & Minor, 1997)'
_computing_structure_solution    'SIR97 (Altomare et al., 1999)'
_computing_structure_refinement  'SHELXL-2014 (Sheldrick, 2015)'
_computing_molecular_graphics    
'ORTEP-3 for Windows version 2.02 (Farrugia, 2008)'
_computing_publication_material  'WinGX publication routines (Farrugia, 1999)'

_refine_special_details          
;
 ?
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0830P)²+0.5130P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         6609
_refine_ls_number_parameters     398
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0486
_refine_ls_R_factor_gt           0.0434
_refine_ls_wR_factor_ref         0.1271
_refine_ls_wR_factor_gt          0.1202
_refine_ls_goodness_of_fit_ref   1.026
_refine_ls_restrained_S_all      1.026
_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_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Zn1 Zn 0.29826(2) 0.31755(2) 0.75268(2) 0.04226(10) Uani 1 1 d . . . . .
N3 N 0.16464(17) 0.50080(15) 0.78766(14) 0.0418(4) Uani 1 1 d . . . . .
N4 N -0.0755(3) 0.8985(2) 0.6212(2) 0.0811(8) Uani 1 1 d . . . . .
N1 N 0.11879(17) 0.25729(15) 0.73925(13) 0.0407(3) Uani 1 1 d . . . . .
N2 N -0.1456(3) 0.0270(4) 0.9366(3) 0.1027(11) Uani 1 1 d . . . . .
N5 N 0.46790(18) 0.38241(16) 0.74037(14) 0.0449(4) Uani 1 1 d . . . . .
N6 N 0.80746(19) 0.49936(18) 0.72845(16) 0.0501(4) Uani 1 1 d . . . . .
H6A H 0.8440 0.5015 0.7873 0.075 Uiso 1 1 calc R U . . .
H6B H 0.8404 0.5219 0.6675 0.075 Uiso 1 1 calc R U . . .
N7 N 0.4254(2) 0.13925(16) 0.75086(15) 0.0472(4) Uani 1 1 d . . . . .
N8 N 0.6851(2) -0.20788(19) 0.7486(2) 0.0658(6) Uani 1 1 d . . . . .
H8A H 0.7121 -0.2533 0.8083 0.099 Uiso 1 1 calc R U . . .
H8B H 0.7098 -0.2348 0.6886 0.099 Uiso 1 1 calc R U . . .
O3 O 0.27907(16) 0.29953(13) 0.92092(11) 0.0468(3) Uani 1 1 d . . . . .
O4 O 0.22083(18) 0.39541(15) 1.06382(12) 0.0545(4) Uani 1 1 d . . . . .
O1 O 0.25118(17) 0.36719(15) 0.59007(12) 0.0502(4) Uani 1 1 d . . . . .
O2 O 0.1150(3) 0.3648(3) 0.46176(15) 0.0926(8) Uani 1 1 d . . . . .
C8 C 0.22453(19) 0.39103(18) 0.96638(15) 0.0395(4) Uani 1 1 d . . . . .
C9 C 0.15557(19) 0.50756(18) 0.89337(15) 0.0391(4) Uani 1 1 d . . . . .
C10 C 0.0879(2) 0.6120(2) 0.93393(18) 0.0504(5) Uani 1 1 d . . . . .
H3 H 0.0833 0.6136 1.0077 0.060 Uiso 1 1 calc R U . . .
C11 C 0.0268(3) 0.7144(2) 0.8638(2) 0.0570(5) Uani 1 1 d . . . . .
H4 H -0.0189 0.7862 0.8893 0.068 Uiso 1 1 calc R U . . .
C12 C 0.0350(2) 0.7080(2) 0.75496(19) 0.0491(5) Uani 1 1 d . . . . .
C13 C 0.1049(2) 0.59935(19) 0.71950(17) 0.0463(4) Uani 1 1 d . . . . .
H6 H 0.1103 0.5952 0.6461 0.056 Uiso 1 1 calc R U . . .
C14 C -0.0263(3) 0.8137(2) 0.6793(2) 0.0590(6) Uani 1 1 d . . . . .
C1 C 0.1533(3) 0.3437(2) 0.55519(17) 0.0522(5) Uani 1 1 d . . . . .
C2 C 0.0744(2) 0.28067(18) 0.63823(16) 0.0432(4) Uani 1 1 d . . . . .
C3 C -0.0332(2) 0.2473(2) 0.60918(18) 0.0521(5) Uani 1 1 d . . . . .
H10 H -0.0634 0.2668 0.5387 0.063 Uiso 1 1 calc R U . . .
C4 C -0.0951(2) 0.1843(2) 0.6869(2) 0.0531(5) Uani 1 1 d . . . . .
H11 H -0.1670 0.1600 0.6696 0.064 Uiso 1 1 calc R U . . .
C5 C -0.0474(2) 0.1583(2) 0.79087(18) 0.0482(5) Uani 1 1 d . . . . .
C6 C 0.0589(2) 0.19733(19) 0.81439(17) 0.0454(4) Uani 1 1 d . . . . .
H13 H 0.0892 0.1811 0.8847 0.054 Uiso 1 1 calc R U . . .
C7 C -0.1036(3) 0.0865(3) 0.8731(2) 0.0666(7) Uani 1 1 d . . . . .
C15 C 0.5304(2) 0.3866(2) 0.82967(17) 0.0509(5) Uani 1 1 d . . . . .
H15 H 0.4951 0.3629 0.8959 0.061 Uiso 1 1 calc R U . . .
C16 C 0.6421(2) 0.4233(2) 0.82934(17) 0.0496(5) Uani 1 1 d . . . . .
H16 H 0.6807 0.4236 0.8940 0.059 Uiso 1 1 calc R U . . .
C17 C 0.6984(2) 0.46066(17) 0.73173(16) 0.0416(4) Uani 1 1 d . . . . .
C18 C 0.6366(2) 0.4520(2) 0.63821(17) 0.0496(5) Uani 1 1 d . . . . .
H18 H 0.6716 0.4720 0.5708 0.060 Uiso 1 1 calc R U . . .
C19 C 0.5249(2) 0.4142(2) 0.64672(17) 0.0495(5) Uani 1 1 d . . . . .
H19 H 0.4858 0.4101 0.5835 0.059 Uiso 1 1 calc R U . . .
C20 C 0.4716(3) 0.0960(2) 0.66010(19) 0.0595(6) Uani 1 1 d . . . . .
H20 H 0.4425 0.1454 0.5956 0.071 Uiso 1 1 calc R U . . .
C21 C 0.5590(3) -0.0160(2) 0.6548(2) 0.0611(6) Uani 1 1 d . . . . .
H21 H 0.5884 -0.0399 0.5883 0.073 Uiso 1 1 calc R U . . .
C22 C 0.6040(2) -0.0944(2) 0.74904(19) 0.0502(5) Uani 1 1 d . . . . .
C23 C 0.5618(3) -0.0473(3) 0.8435(2) 0.0713(8) Uani 1 1 d . . . . .
H23 H 0.5933 -0.0929 0.9091 0.086 Uiso 1 1 calc R U . . .
C24 C 0.4744(3) 0.0655(3) 0.8411(2) 0.0698(8) Uani 1 1 d . . . . .
H24 H 0.4468 0.0933 0.9065 0.084 Uiso 1 1 calc R U . . .
C25 C 0.3815(5) 0.7340(6) 0.8964(4) 0.1255(19) Uani 1 1 d . . . . .
H25A H 0.3729 0.6538 0.9126 0.188 Uiso 1 1 calc R U . . .
H25B H 0.3250 0.7846 0.9440 0.188 Uiso 1 1 calc R U . . .
H25C H 0.4725 0.7313 0.9056 0.188 Uiso 1 1 calc R U . . .
C26 C 0.3419(3) 0.7839(3) 0.7841(3) 0.0759(8) Uani 1 1 d . . . . .
C27 C 0.3858(4) 0.7141(3) 0.7113(4) 0.0930(11) Uani 1 1 d . . . . .
H27 H 0.4428 0.6365 0.7298 0.112 Uiso 1 1 calc R U . . .
C28 C 0.3438(5) 0.7600(4) 0.5972(4) 0.1100(14) Uani 1 1 d . . . . .
H28 H 0.3720 0.7103 0.5442 0.132 Uiso 1 1 calc R U . . .
C29 C 0.2691(4) 0.8675(4) 0.5736(3) 0.0963(12) Uani 1 1 d . . . . .
H29 H 0.2445 0.8961 0.5024 0.116 Uiso 1 1 calc R U . . .
C30 C 0.2232(4) 0.9433(3) 0.6501(4) 0.0984(12) Uani 1 1 d . . . . .
H30 H 0.1709 1.0226 0.6303 0.118 Uiso 1 1 calc R U . . .
C31 C 0.2555(3) 0.9006(3) 0.7553(3) 0.0791(9) Uani 1 1 d . . . . .
H31 H 0.2200 0.9491 0.8081 0.095 Uiso 1 1 calc R U . . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Zn1 O1 2.0845(14) . ?
Zn1 O3 2.0992(14) . ?
Zn1 N7 2.1183(18) . ?
Zn1 N5 2.1256(18) . ?
Zn1 N1 2.2246(17) . ?
Zn1 N3 2.2779(18) . ?
N3 C13 1.336(3) . ?
N3 C9 1.341(3) . ?
N4 C14 1.141(3) . ?
N1 C6 1.333(3) . ?
N1 C2 1.339(2) . ?
N2 C7 1.136(4) . ?
N5 C19 1.343(3) . ?
N5 C15 1.347(3) . ?
N6 C17 1.349(3) . ?
N6 H6A 0.8600 . ?
N6 H6B 0.8600 . ?
N7 C20 1.329(3) . ?
N7 C24 1.341(3) . ?
N8 C22 1.348(3) . ?
N8 H8A 0.8600 . ?
N8 H8B 0.8600 . ?
O3 C8 1.260(3) . ?
O4 C8 1.233(2) . ?
O1 C1 1.258(3) . ?
O2 C1 1.229(3) . ?
C8 C9 1.526(3) . ?
C9 C10 1.376(3) . ?
C10 C11 1.381(3) . ?
C10 H3 0.9300 . ?
C11 C12 1.379(4) . ?
C11 H4 0.9300 . ?
C12 C13 1.391(3) . ?
C12 C14 1.443(3) . ?
C13 H6 0.9300 . ?
C1 C2 1.534(3) . ?
C2 C3 1.386(3) . ?
C3 C4 1.383(3) . ?
C3 H10 0.9300 . ?
C4 C5 1.384(3) . ?
C4 H11 0.9300 . ?
C5 C6 1.387(3) . ?
C5 C7 1.444(3) . ?
C6 H13 0.9300 . ?
C15 C16 1.365(3) . ?
C15 H15 0.9300 . ?
C16 C17 1.399(3) . ?
C16 H16 0.9300 . ?
C17 C18 1.406(3) . ?
C18 C19 1.366(3) . ?
C18 H18 0.9300 . ?
C19 H19 0.9300 . ?
C20 C21 1.367(3) . ?
C20 H20 0.9300 . ?
C21 C22 1.393(3) . ?
C21 H21 0.9300 . ?
C22 C23 1.382(4) . ?
C23 C24 1.362(4) . ?
C23 H23 0.9300 . ?
C24 H24 0.9300 . ?
C25 C26 1.476(5) . ?
C25 H25A 0.9600 . ?
C25 H25B 0.9600 . ?
C25 H25C 0.9600 . ?
C26 C27 1.294(5) . ?
C26 C31 1.402(5) . ?
C27 C28 1.496(6) . ?
C27 H27 0.9300 . ?
C28 C29 1.268(6) . ?
C28 H28 0.9300 . ?
C29 C30 1.380(6) . ?
C29 H29 0.9300 . ?
C30 C31 1.364(6) . ?
C30 H30 0.9300 . ?
C31 H31 0.9300 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
O1 Zn1 O3 161.02(7) . . ?
O1 Zn1 N7 100.25(7) . . ?
O3 Zn1 N7 94.59(6) . . ?
O1 Zn1 N5 94.93(6) . . ?
O3 Zn1 N5 96.94(7) . . ?
N7 Zn1 N5 89.65(7) . . ?
O1 Zn1 N1 76.60(6) . . ?
O3 Zn1 N1 91.40(6) . . ?
N7 Zn1 N1 91.28(7) . . ?
N5 Zn1 N1 171.51(6) . . ?
O1 Zn1 N3 90.07(6) . . ?
O3 Zn1 N3 75.05(6) . . ?
N7 Zn1 N3 169.60(6) . . ?
N5 Zn1 N3 90.78(7) . . ?
N1 Zn1 N3 89.83(6) . . ?
C13 N3 C9 118.48(18) . . ?
C13 N3 Zn1 129.61(15) . . ?
C9 N3 Zn1 111.74(13) . . ?
C6 N1 C2 118.71(18) . . ?
C6 N1 Zn1 129.15(14) . . ?
C2 N1 Zn1 112.00(13) . . ?
C19 N5 C15 115.58(19) . . ?
C19 N5 Zn1 123.99(14) . . ?
C15 N5 Zn1 120.30(15) . . ?
C17 N6 H6A 120.0 . . ?
C17 N6 H6B 120.0 . . ?
H6A N6 H6B 120.0 . . ?
C20 N7 C24 114.9(2) . . ?
C20 N7 Zn1 122.45(15) . . ?
C24 N7 Zn1 122.38(17) . . ?
C22 N8 H8A 120.0 . . ?
C22 N8 H8B 120.0 . . ?
H8A N8 H8B 120.0 . . ?
C8 O3 Zn1 120.13(12) . . ?
C1 O1 Zn1 119.40(14) . . ?
O4 C8 O3 126.44(19) . . ?
O4 C8 C9 116.97(18) . . ?
O3 C8 C9 116.59(16) . . ?
N3 C9 C10 122.53(18) . . ?
N3 C9 C8 115.54(17) . . ?
C10 C9 C8 121.93(18) . . ?
C9 C10 C11 119.2(2) . . ?
C9 C10 H3 120.4 . . ?
C11 C10 H3 120.4 . . ?
C12 C11 C10 118.6(2) . . ?
C12 C11 H4 120.7 . . ?
C10 C11 H4 120.7 . . ?
C11 C12 C13 119.1(2) . . ?
C11 C12 C14 120.0(2) . . ?
C13 C12 C14 120.8(2) . . ?
N3 C13 C12 122.0(2) . . ?
N3 C13 H6 119.0 . . ?
C12 C13 H6 119.0 . . ?
N4 C14 C12 178.7(3) . . ?
O2 C1 O1 127.0(2) . . ?
O2 C1 C2 116.6(2) . . ?
O1 C1 C2 116.36(17) . . ?
N1 C2 C3 122.6(2) . . ?
N1 C2 C1 115.63(18) . . ?
C3 C2 C1 121.76(18) . . ?
C4 C3 C2 118.8(2) . . ?
C4 C3 H10 120.6 . . ?
C2 C3 H10 120.6 . . ?
C3 C4 C5 118.4(2) . . ?
C3 C4 H11 120.8 . . ?
C5 C4 H11 120.8 . . ?
C4 C5 C6 119.4(2) . . ?
C4 C5 C7 120.3(2) . . ?
C6 C5 C7 120.2(2) . . ?
N1 C6 C5 122.00(19) . . ?
N1 C6 H13 119.0 . . ?
C5 C6 H13 119.0 . . ?
N2 C7 C5 177.9(4) . . ?
N5 C15 C16 124.3(2) . . ?
N5 C15 H15 117.8 . . ?
C16 C15 H15 117.8 . . ?
C15 C16 C17 119.96(19) . . ?
C15 C16 H16 120.0 . . ?
C17 C16 H16 120.0 . . ?
N6 C17 C16 121.54(19) . . ?
N6 C17 C18 122.5(2) . . ?
C16 C17 C18 115.9(2) . . ?
C19 C18 C17 119.8(2) . . ?
C19 C18 H18 120.1 . . ?
C17 C18 H18 120.1 . . ?
N5 C19 C18 124.4(2) . . ?
N5 C19 H19 117.8 . . ?
C18 C19 H19 117.8 . . ?
N7 C20 C21 124.7(2) . . ?
N7 C20 H20 117.7 . . ?
C21 C20 H20 117.7 . . ?
C20 C21 C22 120.0(2) . . ?
C20 C21 H21 120.0 . . ?
C22 C21 H21 120.0 . . ?
N8 C22 C23 122.0(2) . . ?
N8 C22 C21 122.5(2) . . ?
C23 C22 C21 115.5(2) . . ?
C24 C23 C22 120.3(2) . . ?
C24 C23 H23 119.8 . . ?
C22 C23 H23 119.8 . . ?
N7 C24 C23 124.4(2) . . ?
N7 C24 H24 117.8 . . ?
C23 C24 H24 117.8 . . ?
C26 C25 H25A 109.5 . . ?
C26 C25 H25B 109.5 . . ?
H25A C25 H25B 109.5 . . ?
C26 C25 H25C 109.5 . . ?
H25A C25 H25C 109.5 . . ?
H25B C25 H25C 109.5 . . ?
C27 C26 C31 119.8(4) . . ?
C27 C26 C25 117.7(4) . . ?
C31 C26 C25 122.5(4) . . ?
C26 C27 C28 119.2(3) . . ?
C26 C27 H27 120.4 . . ?
C28 C27 H27 120.4 . . ?
C29 C28 C27 119.2(4) . . ?
C29 C28 H28 120.4 . . ?
C27 C28 H28 120.4 . . ?
C28 C29 C30 122.2(4) . . ?
C28 C29 H29 118.9 . . ?
C30 C29 H29 118.9 . . ?
C31 C30 C29 119.2(3) . . ?
C31 C30 H30 120.4 . . ?
C29 C30 H30 120.4 . . ?
C30 C31 C26 120.3(3) . . ?
C30 C31 H31 119.8 . . ?
C26 C31 H31 119.8 . . ?

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
Zn1 O3 C8 O4 -171.00(17) . . . . ?
Zn1 O3 C8 C9 9.4(2) . . . . ?
C13 N3 C9 C10 -0.3(3) . . . . ?
Zn1 N3 C9 C10 175.49(17) . . . . ?
C13 N3 C9 C8 179.17(17) . . . . ?
Zn1 N3 C9 C8 -5.0(2) . . . . ?
O4 C8 C9 N3 178.15(18) . . . . ?
O3 C8 C9 N3 -2.2(3) . . . . ?
O4 C8 C9 C10 -2.4(3) . . . . ?
O3 C8 C9 C10 177.3(2) . . . . ?
N3 C9 C10 C11 -0.2(3) . . . . ?
C8 C9 C10 C11 -179.6(2) . . . . ?
C9 C10 C11 C12 0.5(4) . . . . ?
C10 C11 C12 C13 -0.5(4) . . . . ?
C10 C11 C12 C14 -179.3(2) . . . . ?
C9 N3 C13 C12 0.4(3) . . . . ?
Zn1 N3 C13 C12 -174.54(15) . . . . ?
C11 C12 C13 N3 0.0(3) . . . . ?
C14 C12 C13 N3 178.8(2) . . . . ?
Zn1 O1 C1 O2 -178.4(3) . . . . ?
Zn1 O1 C1 C2 0.9(3) . . . . ?
C6 N1 C2 C3 1.4(3) . . . . ?
Zn1 N1 C2 C3 177.50(18) . . . . ?
C6 N1 C2 C1 -176.70(19) . . . . ?
Zn1 N1 C2 C1 -0.6(2) . . . . ?
O2 C1 C2 N1 179.3(3) . . . . ?
O1 C1 C2 N1 -0.1(3) . . . . ?
O2 C1 C2 C3 1.1(4) . . . . ?
O1 C1 C2 C3 -178.3(2) . . . . ?
N1 C2 C3 C4 -1.8(4) . . . . ?
C1 C2 C3 C4 176.2(2) . . . . ?
C2 C3 C4 C5 0.6(4) . . . . ?
C3 C4 C5 C6 0.9(3) . . . . ?
C3 C4 C5 C7 -176.2(2) . . . . ?
C2 N1 C6 C5 0.2(3) . . . . ?
Zn1 N1 C6 C5 -175.08(15) . . . . ?
C4 C5 C6 N1 -1.4(3) . . . . ?
C7 C5 C6 N1 175.8(2) . . . . ?
C19 N5 C15 C16 1.9(4) . . . . ?
Zn1 N5 C15 C16 177.94(19) . . . . ?
N5 C15 C16 C17 0.4(4) . . . . ?
C15 C16 C17 N6 178.9(2) . . . . ?
C15 C16 C17 C18 -2.8(3) . . . . ?
N6 C17 C18 C19 -178.9(2) . . . . ?
C16 C17 C18 C19 2.9(3) . . . . ?
C15 N5 C19 C18 -1.8(3) . . . . ?
Zn1 N5 C19 C18 -177.67(18) . . . . ?
C17 C18 C19 N5 -0.6(4) . . . . ?
C24 N7 C20 C21 2.1(4) . . . . ?
Zn1 N7 C20 C21 176.5(2) . . . . ?
N7 C20 C21 C22 1.1(5) . . . . ?
C20 C21 C22 N8 176.7(3) . . . . ?
C20 C21 C22 C23 -4.4(4) . . . . ?
N8 C22 C23 C24 -176.6(3) . . . . ?
C21 C22 C23 C24 4.5(5) . . . . ?
C20 N7 C24 C23 -2.0(5) . . . . ?
Zn1 N7 C24 C23 -176.4(3) . . . . ?
C22 C23 C24 N7 -1.4(6) . . . . ?
C31 C26 C27 C28 0.3(6) . . . . ?
C25 C26 C27 C28 177.8(4) . . . . ?
C26 C27 C28 C29 2.0(7) . . . . ?
C27 C28 C29 C30 -1.1(8) . . . . ?
C28 C29 C30 C31 -2.1(7) . . . . ?
C29 C30 C31 C26 4.5(6) . . . . ?
C27 C26 C31 C30 -3.6(6) . . . . ?
C25 C26 C31 C30 179.0(4) . . . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
N6 H6A O4 0.86 2.34 3.020(2) 135.8 2_667
N6 H6B O2 0.86 2.06 2.881(3) 159.4 2_666
N8 H8A O4 0.86 2.11 2.956(3) 167.6 2_657
C15 H15 O3 0.93 2.58 3.199(3) 124.5 .
C19 H19 O1 0.93 2.65 3.222(3) 120.1 .
C24 H24 O3 0.93 2.55 3.160(3) 123.0 .

_refine_diff_density_max         0.933
_refine_diff_density_min         -0.443
_refine_diff_density_rms         0.055

_shelxl_version_number           2014-3

####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_8
_database_code_depnum_ccdc_archive 'CCDC 1480533'
_audit_update_record             
;
2016-05-17 deposited with the CCDC.
2016-12-07 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
 ?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C19 H12 N6 O4 Zn'
_chemical_formula_sum            'C19 H12 N6 O4 Zn'
_chemical_formula_weight         453.72

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 '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 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Zn Zn -1.5491 0.6778 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 21/c'
_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                   10.13000(10)
_cell_length_b                   11.4236(2)
_cell_length_c                   17.9233(3)
_cell_angle_alpha                90.00
_cell_angle_beta                 114.1460(10)
_cell_angle_gamma                90.00
_cell_volume                     1892.63(5)
_cell_formula_units_Z            4
_cell_measurement_temperature    150(2)
_cell_measurement_reflns_used    6551
_cell_measurement_theta_min      3.8610
_cell_measurement_theta_max      74.4780

_exptl_crystal_description       prism
_exptl_crystal_colour            colorless
_exptl_crystal_size_max          0.12
_exptl_crystal_size_mid          0.10
_exptl_crystal_size_min          0.07
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.592
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             920
_exptl_absorpt_coefficient_mu    2.168
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.98375
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_process_details   '(CrysAlis PRO; Agilent, 2013)'

_exptl_special_details           
;
23 runs of ω scans. Crystal-detector distance = 55.0 mm. 
;

_diffrn_ambient_temperature      150(2)
_diffrn_radiation_wavelength     1.54184
_diffrn_radiation_type           CuK\a
_diffrn_radiation_source         'SuperNova (Cu) X-ray Source'
_diffrn_radiation_monochromator  Mirror
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, Atlas'
_diffrn_measurement_method       'ω scans'
_diffrn_detector_area_resol_mean 10.4933
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            11961
_diffrn_reflns_av_R_equivalents  0.0239
_diffrn_reflns_av_sigmaI/netI    0.0229
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_theta_min         4.72
_diffrn_reflns_theta_max         74.83
_reflns_number_total             3880
_reflns_number_gt                3415
_reflns_threshold_expression     >2σ(I)

_computing_data_collection       'CrysAlis PRO (Agilent, 2013)'
_computing_cell_refinement       'CrysAlis PRO (Agilent, 2013)'
_computing_data_reduction        'CrysAlis PRO (Agilent, 2013)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_molecular_graphics    
'ORTEP-3 for Windows version 2.02 (Farrugia, 2008)'
_computing_publication_material  'WinGX publication routines (Farrugia, 1999)'

_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)+(0.0352P)²+0.8941P] 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         3880
_refine_ls_number_parameters     271
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0334
_refine_ls_R_factor_gt           0.0279
_refine_ls_wR_factor_ref         0.0729
_refine_ls_wR_factor_gt          0.0688
_refine_ls_goodness_of_fit_ref   1.060
_refine_ls_restrained_S_all      1.060
_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 0.65460(2) 0.553632(19) 0.290887(14) 0.01890(8) Uani 1 1 d . . .
N1 N 0.87288(15) 0.58808(13) 0.37264(9) 0.0210(3) Uani 1 1 d . . .
N2 N 1.3303(2) 0.3997(2) 0.51124(12) 0.0443(5) Uani 1 1 d . . .
N3 N 0.43925(15) 0.54485(12) 0.27716(9) 0.0194(3) Uani 1 1 d . . .
N4 N 0.0043(2) 0.76913(17) 0.18486(16) 0.0508(6) Uani 1 1 d . . .
N5 N 0.66689(15) 0.50840(12) 0.18561(9) 0.0199(3) Uani 1 1 d . . .
N6 N 0.68081(17) 0.42973(13) -0.03799(9) 0.0242(3) Uani 1 1 d . . .
H6A H 0.7230 0.4787 -0.0593 0.036 Uiso 1 1 calc R . .
H6B H 0.6408 0.3651 -0.0643 0.036 Uiso 1 1 calc R . .
O1 O 0.64866(13) 0.73072(11) 0.30729(8) 0.0239(3) Uani 1 1 d . . .
O2 O 0.77466(15) 0.88143(11) 0.38356(8) 0.0297(3) Uani 1 1 d . . .
O3 O 0.65385(13) 0.39280(10) 0.34167(7) 0.0225(2) Uani 1 1 d . . .
O4 O 0.51869(14) 0.27610(11) 0.38262(8) 0.0277(3) Uani 1 1 d . . .
C1 C 0.76197(19) 0.77948(15) 0.35926(11) 0.0224(3) Uani 1 1 d . . .
C2 C 0.89556(19) 0.70187(15) 0.39332(10) 0.0217(3) Uani 1 1 d . . .
C3 C 1.0312(2) 0.74516(17) 0.44280(12) 0.0295(4) Uani 1 1 d . . .
H3 H 1.0441 0.8260 0.4563 0.035 Uiso 1 1 calc R . .
C4 C 1.1476(2) 0.66869(18) 0.47228(12) 0.0301(4) Uani 1 1 d . . .
H4 H 1.2420 0.6963 0.5054 0.036 Uiso 1 1 calc R . .
C5 C 1.12312(19) 0.55077(17) 0.45226(11) 0.0250(4) Uani 1 1 d . . .
C6 C 0.98343(19) 0.51357(16) 0.40208(11) 0.0240(4) Uani 1 1 d . . .
H6 H 0.9668 0.4329 0.3886 0.029 Uiso 1 1 calc R . .
C7 C 1.2388(2) 0.46621(19) 0.48447(12) 0.0310(4) Uani 1 1 d . . .
C8 C 0.53735(18) 0.36397(15) 0.34816(10) 0.0205(3) Uani 1 1 d . . .
C9 C 0.41081(18) 0.44776(14) 0.30972(10) 0.0193(3) Uani 1 1 d . . .
C10 C 0.27549(19) 0.42463(15) 0.30829(11) 0.0225(3) Uani 1 1 d . . .
H10 H 0.2585 0.3548 0.3318 0.027 Uiso 1 1 calc R . .
C11 C 0.16609(19) 0.50474(16) 0.27216(11) 0.0240(4) Uani 1 1 d . . .
H11 H 0.0714 0.4903 0.2687 0.029 Uiso 1 1 calc R . .
C12 C 0.19753(19) 0.60739(15) 0.24084(11) 0.0234(3) Uani 1 1 d . . .
C13 C 0.33548(18) 0.62452(15) 0.24350(11) 0.0218(3) Uani 1 1 d . . .
H13 H 0.3560 0.6939 0.2210 0.026 Uiso 1 1 calc R . .
C14 C 0.0902(2) 0.69785(17) 0.20816(14) 0.0323(4) Uani 1 1 d . . .
C15 C 0.60738(18) 0.40880(15) 0.14465(11) 0.0220(3) Uani 1 1 d . . .
H15 H 0.5606 0.3574 0.1678 0.026 Uiso 1 1 calc R . .
C16 C 0.61112(18) 0.37828(14) 0.07146(11) 0.0217(3) Uani 1 1 d . . .
H16 H 0.5691 0.3067 0.0456 0.026 Uiso 1 1 calc R . .
C17 C 0.67757(18) 0.45361(14) 0.03479(11) 0.0203(3) Uani 1 1 d . . .
C18 C 0.74074(19) 0.55620(15) 0.07804(11) 0.0236(4) Uani 1 1 d . . .
H18 H 0.7890 0.6092 0.0569 0.028 Uiso 1 1 calc R . .
C19 C 0.73210(19) 0.57915(15) 0.15097(11) 0.0231(3) Uani 1 1 d . . .
H19 H 0.7748 0.6494 0.1788 0.028 Uiso 1 1 calc R . .


_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 N5 2.0088(14) . ?
Zn1 O1 2.0486(12) . ?
Zn1 O3 2.0518(12) . ?
Zn1 N3 2.0953(14) . ?
Zn1 N1 2.1309(15) . ?
N1 C6 1.332(2) . ?
N1 C2 1.345(2) . ?
N2 C7 1.142(3) . ?
N3 C13 1.334(2) . ?
N3 C9 1.338(2) . ?
N4 C14 1.139(3) . ?
N5 C19 1.346(2) . ?
N5 C15 1.355(2) . ?
N6 C17 1.346(2) . ?
N6 H6A 0.8800 . ?
N6 H6B 0.8800 . ?
O1 C1 1.273(2) . ?
O2 C1 1.232(2) . ?
O3 C8 1.276(2) . ?
O4 C8 1.233(2) . ?
C1 C2 1.521(2) . ?
C2 C3 1.386(2) . ?
C3 C4 1.387(3) . ?
C3 H3 0.9500 . ?
C4 C5 1.390(3) . ?
C4 H4 0.9500 . ?
C5 C6 1.397(2) . ?
C5 C7 1.444(3) . ?
C6 H6 0.9500 . ?
C8 C9 1.520(2) . ?
C9 C10 1.386(2) . ?
C10 C11 1.378(2) . ?
C10 H10 0.9500 . ?
C11 C12 1.392(2) . ?
C11 H11 0.9500 . ?
C12 C13 1.392(2) . ?
C12 C14 1.440(2) . ?
C13 H13 0.9500 . ?
C15 C16 1.373(2) . ?
C15 H15 0.9500 . ?
C16 C17 1.410(2) . ?
C16 H16 0.9500 . ?
C17 C18 1.406(2) . ?
C18 C19 1.371(3) . ?
C18 H18 0.9500 . ?
C19 H19 0.9500 . ?

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
N5 Zn1 O1 113.92(6) . . ?
N5 Zn1 O3 101.49(5) . . ?
O1 Zn1 O3 144.58(5) . . ?
N5 Zn1 N3 109.81(6) . . ?
O1 Zn1 N3 88.50(5) . . ?
O3 Zn1 N3 79.43(5) . . ?
N5 Zn1 N1 104.35(6) . . ?
O1 Zn1 N1 78.59(5) . . ?
O3 Zn1 N1 92.95(5) . . ?
N3 Zn1 N1 145.82(6) . . ?
C6 N1 C2 119.16(15) . . ?
C6 N1 Zn1 128.49(12) . . ?
C2 N1 Zn1 112.34(12) . . ?
C13 N3 C9 119.49(15) . . ?
C13 N3 Zn1 127.63(11) . . ?
C9 N3 Zn1 112.83(11) . . ?
C19 N5 C15 116.62(15) . . ?
C19 N5 Zn1 120.65(12) . . ?
C15 N5 Zn1 122.71(12) . . ?
C17 N6 H6A 120.0 . . ?
C17 N6 H6B 120.0 . . ?
H6A N6 H6B 120.0 . . ?
C1 O1 Zn1 117.80(11) . . ?
C8 O3 Zn1 116.30(11) . . ?
O2 C1 O1 127.22(17) . . ?
O2 C1 C2 117.53(16) . . ?
O1 C1 C2 115.24(15) . . ?
N1 C2 C3 122.26(17) . . ?
N1 C2 C1 115.40(15) . . ?
C3 C2 C1 122.33(16) . . ?
C2 C3 C4 119.01(18) . . ?
C2 C3 H3 120.5 . . ?
C4 C3 H3 120.5 . . ?
C3 C4 C5 118.54(17) . . ?
C3 C4 H4 120.7 . . ?
C5 C4 H4 120.7 . . ?
C4 C5 C6 119.21(17) . . ?
C4 C5 C7 120.99(17) . . ?
C6 C5 C7 119.77(17) . . ?
N1 C6 C5 121.80(17) . . ?
N1 C6 H6 119.1 . . ?
C5 C6 H6 119.1 . . ?
N2 C7 C5 178.8(2) . . ?
O4 C8 O3 126.37(16) . . ?
O4 C8 C9 117.78(15) . . ?
O3 C8 C9 115.86(14) . . ?
N3 C9 C10 122.52(16) . . ?
N3 C9 C8 115.30(15) . . ?
C10 C9 C8 122.18(15) . . ?
C11 C10 C9 118.78(16) . . ?
C11 C10 H10 120.6 . . ?
C9 C10 H10 120.6 . . ?
C10 C11 C12 118.44(16) . . ?
C10 C11 H11 120.8 . . ?
C12 C11 H11 120.8 . . ?
C11 C12 C13 119.77(16) . . ?
C11 C12 C14 120.62(16) . . ?
C13 C12 C14 119.57(16) . . ?
N3 C13 C12 120.92(16) . . ?
N3 C13 H13 119.5 . . ?
C12 C13 H13 119.5 . . ?
N4 C14 C12 177.5(2) . . ?
N5 C15 C16 123.44(16) . . ?
N5 C15 H15 118.3 . . ?
C16 C15 H15 118.3 . . ?
C15 C16 C17 119.70(16) . . ?
C15 C16 H16 120.1 . . ?
C17 C16 H16 120.1 . . ?
N6 C17 C18 121.13(16) . . ?
N6 C17 C16 122.25(16) . . ?
C18 C17 C16 116.62(16) . . ?
C19 C18 C17 119.53(16) . . ?
C19 C18 H18 120.2 . . ?
C17 C18 H18 120.2 . . ?
N5 C19 C18 124.06(16) . . ?
N5 C19 H19 118.0 . . ?
C18 C19 H19 118.0 . . ?

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
N5 Zn1 N1 C6 -65.75(15) . . . . ?
O1 Zn1 N1 C6 -177.79(16) . . . . ?
O3 Zn1 N1 C6 36.91(15) . . . . ?
N3 Zn1 N1 C6 112.37(16) . . . . ?
N5 Zn1 N1 C2 112.57(12) . . . . ?
O1 Zn1 N1 C2 0.52(11) . . . . ?
O3 Zn1 N1 C2 -144.78(12) . . . . ?
N3 Zn1 N1 C2 -69.31(16) . . . . ?
N5 Zn1 N3 C13 -81.04(15) . . . . ?
O1 Zn1 N3 C13 33.91(15) . . . . ?
O3 Zn1 N3 C13 -179.56(15) . . . . ?
N1 Zn1 N3 C13 100.90(17) . . . . ?
N5 Zn1 N3 C9 101.45(12) . . . . ?
O1 Zn1 N3 C9 -143.60(12) . . . . ?
O3 Zn1 N3 C9 2.93(11) . . . . ?
N1 Zn1 N3 C9 -76.61(15) . . . . ?
O1 Zn1 N5 C19 29.45(15) . . . . ?
O3 Zn1 N5 C19 -150.33(13) . . . . ?
N3 Zn1 N5 C19 126.89(13) . . . . ?
N1 Zn1 N5 C19 -54.23(14) . . . . ?
O1 Zn1 N5 C15 -148.44(12) . . . . ?
O3 Zn1 N5 C15 31.77(14) . . . . ?
N3 Zn1 N5 C15 -51.01(14) . . . . ?
N1 Zn1 N5 C15 127.87(13) . . . . ?
N5 Zn1 O1 C1 -106.30(13) . . . . ?
O3 Zn1 O1 C1 73.33(15) . . . . ?
N3 Zn1 O1 C1 142.64(13) . . . . ?
N1 Zn1 O1 C1 -5.52(12) . . . . ?
N5 Zn1 O3 C8 -113.21(12) . . . . ?
O1 Zn1 O3 C8 67.14(15) . . . . ?
N3 Zn1 O3 C8 -4.91(12) . . . . ?
N1 Zn1 O3 C8 141.50(12) . . . . ?
Zn1 O1 C1 O2 -171.96(15) . . . . ?
Zn1 O1 C1 C2 8.96(19) . . . . ?
C6 N1 C2 C3 1.6(3) . . . . ?
Zn1 N1 C2 C3 -176.88(14) . . . . ?
C6 N1 C2 C1 -177.89(15) . . . . ?
Zn1 N1 C2 C1 3.62(18) . . . . ?
O2 C1 C2 N1 172.47(16) . . . . ?
O1 C1 C2 N1 -8.4(2) . . . . ?
O2 C1 C2 C3 -7.0(3) . . . . ?
O1 C1 C2 C3 172.15(16) . . . . ?
N1 C2 C3 C4 -0.2(3) . . . . ?
C1 C2 C3 C4 179.29(17) . . . . ?
C2 C3 C4 C5 -1.2(3) . . . . ?
C3 C4 C5 C6 1.3(3) . . . . ?
C3 C4 C5 C7 -176.92(18) . . . . ?
C2 N1 C6 C5 -1.6(3) . . . . ?
Zn1 N1 C6 C5 176.61(13) . . . . ?
C4 C5 C6 N1 0.2(3) . . . . ?
C7 C5 C6 N1 178.37(16) . . . . ?
Zn1 O3 C8 O4 -173.79(14) . . . . ?
Zn1 O3 C8 C9 5.79(18) . . . . ?
C13 N3 C9 C10 1.6(3) . . . . ?
Zn1 N3 C9 C10 179.34(13) . . . . ?
C13 N3 C9 C8 -178.69(15) . . . . ?
Zn1 N3 C9 C8 -0.95(18) . . . . ?
O4 C8 C9 N3 176.44(15) . . . . ?
O3 C8 C9 N3 -3.2(2) . . . . ?
O4 C8 C9 C10 -3.9(2) . . . . ?
O3 C8 C9 C10 176.53(16) . . . . ?
N3 C9 C10 C11 -0.2(3) . . . . ?
C8 C9 C10 C11 -179.86(16) . . . . ?
C9 C10 C11 C12 -2.0(3) . . . . ?
C10 C11 C12 C13 2.7(3) . . . . ?
C10 C11 C12 C14 -175.20(18) . . . . ?
C9 N3 C13 C12 -0.8(3) . . . . ?
Zn1 N3 C13 C12 -178.20(13) . . . . ?
C11 C12 C13 N3 -1.3(3) . . . . ?
C14 C12 C13 N3 176.60(18) . . . . ?
C19 N5 C15 C16 0.0(3) . . . . ?
Zn1 N5 C15 C16 178.02(13) . . . . ?
N5 C15 C16 C17 -1.0(3) . . . . ?
C15 C16 C17 N6 -178.09(16) . . . . ?
C15 C16 C17 C18 1.7(2) . . . . ?
N6 C17 C18 C19 178.32(17) . . . . ?
C16 C17 C18 C19 -1.5(3) . . . . ?
C15 N5 C19 C18 0.2(3) . . . . ?
Zn1 N5 C19 C18 -177.83(14) . . . . ?
C17 C18 C19 N5 0.6(3) . . . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
N6 H6A O2 0.88 2.08 2.937(2) 165.4 4_575
N6 H6B O4 0.88 2.02 2.888(2) 169.0 4_565

_diffrn_measured_fraction_theta_max 0.995
_diffrn_reflns_theta_full        74.83
_diffrn_measured_fraction_theta_full 0.995
_refine_diff_density_max         0.244
_refine_diff_density_min         -0.433
_refine_diff_density_rms         0.057
####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_9
_database_code_depnum_ccdc_archive 'CCDC 1480534'
_audit_update_record             
;
2016-05-17 deposited with the CCDC.
2016-12-07 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
 ?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C24 H16 N6 O4 Zn'
_chemical_formula_sum            'C24 H16 N6 O4 Zn'
_chemical_formula_weight         517.80

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 n a 21'
_symmetry_space_group_name_Hall  'P 2c -2n'

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

_cell_length_a                   19.2608(4)
_cell_length_b                   7.14690(10)
_cell_length_c                   17.3723(4)
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_volume                     2391.38(8)
_cell_formula_units_Z            4
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    7961
_cell_measurement_theta_min      2.8443
_cell_measurement_theta_max      30.2837

_exptl_crystal_description       prism
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.25
_exptl_crystal_size_mid          0.25
_exptl_crystal_size_min          0.15
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.438
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1056
_exptl_absorpt_coefficient_mu    1.069
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.7759
_exptl_absorpt_correction_T_max  0.8560
_exptl_absorpt_process_details   '(CrysAlis PRO; Agilent, 2013)'

_exptl_special_details           
;
377 frames in 5 runs of ω scans. Crystal-detector distance = 55.0 mm. 
;

_diffrn_ambient_temperature      293(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'SuperNova (Mo) X-ray Source'
_diffrn_radiation_monochromator  Mirror
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, Atlas'
_diffrn_measurement_method       'ω scans'
_diffrn_detector_area_resol_mean 10.4933
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            20962
_diffrn_reflns_av_R_equivalents  0.0322
_diffrn_reflns_av_sigmaI/netI    0.0268
_diffrn_reflns_limit_h_min       -24
_diffrn_reflns_limit_h_max       25
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_theta_min         3.04
_diffrn_reflns_theta_max         27.48
_reflns_number_total             5465
_reflns_number_gt                4569
_reflns_threshold_expression     >2σ(I)

_computing_data_collection       'CrysAlis PRO (Agilent, 2013)'
_computing_cell_refinement       'CrysAlis PRO (Agilent, 2013)'
_computing_data_reduction        'CrysAlis PRO (Agilent, 2013)'
_computing_structure_solution    'SIR97 (Altomare et al., 1999)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_molecular_graphics    
'ORTEP-3 for Windows version 2.02 (Farrugia, 2008)'
_computing_publication_material  'WinGX publication routines (Farrugia, 1999)'


_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)+(0.0401P)²+0.3815P] 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_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   -0.004(11)
_refine_ls_number_reflns         5465
_refine_ls_number_parameters     316
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0458
_refine_ls_R_factor_gt           0.0342
_refine_ls_wR_factor_ref         0.0849
_refine_ls_wR_factor_gt          0.0788
_refine_ls_goodness_of_fit_ref   1.045
_refine_ls_restrained_S_all      1.045
_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 0.112858(14) 0.32487(4) 0.09477(2) 0.05164(9) Uani 1 1 d . . .
N1 N 0.16911(12) 0.2419(3) 0.20233(13) 0.0495(5) Uani 1 1 d . . .
N2 N 0.31661(18) -0.2293(5) 0.3098(3) 0.1039(12) Uani 1 1 d . . .
N3 N 0.21778(11) 0.3893(3) 0.04861(14) 0.0487(5) Uani 1 1 d . . .
N4 N 0.39407(19) 0.8566(5) 0.0408(4) 0.1272(17) Uani 1 1 d . . .
N5 N 0.01952(13) 0.2013(3) 0.13779(15) 0.0585(6) Uani 1 1 d . . .
N6 N 0.06571(12) 0.4602(3) -0.00139(14) 0.0556(6) Uani 1 1 d . . .
O1 O 0.10915(11) 0.5640(3) 0.16045(13) 0.0603(5) Uani 1 1 d . . .
O2 O 0.13575(13) 0.6955(3) 0.27272(14) 0.0689(6) Uani 1 1 d . . .
O3 O 0.13992(10) 0.0807(3) 0.04085(12) 0.0553(5) Uani 1 1 d . . .
O4 O 0.22372(13) -0.0751(3) -0.01846(15) 0.0747(6) Uani 1 1 d . . .
C1 C 0.13655(14) 0.5653(4) 0.22664(17) 0.0501(6) Uani 1 1 d . . .
C2 C 0.17519(13) 0.3881(4) 0.24985(16) 0.0483(6) Uani 1 1 d . . .
C3 C 0.21517(17) 0.3797(4) 0.31564(19) 0.0631(8) Uani 1 1 d . . .
H3 H 0.2179 0.4827 0.3482 0.076 Uiso 1 1 calc R . .
C4 C 0.25099(18) 0.2184(5) 0.3329(2) 0.0669(8) Uani 1 1 d . . .
H4 H 0.2789 0.2112 0.3765 0.080 Uiso 1 1 calc R . .
C5 C 0.24441(15) 0.0673(4) 0.28368(18) 0.0560(7) Uani 1 1 d . . .
C6 C 0.20266(15) 0.0836(4) 0.21976(18) 0.0549(7) Uani 1 1 d . . .
H6 H 0.1976 -0.0192 0.1875 0.066 Uiso 1 1 calc R . .
C7 C 0.28349(19) -0.1008(5) 0.2985(2) 0.0728(9) Uani 1 1 d . . .
C8 C 0.19917(14) 0.0658(4) 0.01047(16) 0.0481(6) Uani 1 1 d . . .
C9 C 0.24488(13) 0.2413(4) 0.01277(15) 0.0466(6) Uani 1 1 d . . .
C10 C 0.31025(16) 0.2445(5) -0.0195(2) 0.0693(8) Uani 1 1 d . . .
H10 H 0.3279 0.1392 -0.0441 0.083 Uiso 1 1 calc R . .
C11 C 0.34905(17) 0.4056(5) -0.0147(2) 0.0775(10) Uani 1 1 d . . .
H11 H 0.3931 0.4116 -0.0365 0.093 Uiso 1 1 calc R . .
C12 C 0.32163(15) 0.5570(4) 0.0229(2) 0.0649(8) Uani 1 1 d . . .
C13 C 0.25555(15) 0.5454(4) 0.05419(18) 0.0575(7) Uani 1 1 d . . .
H13 H 0.2371 0.6485 0.0797 0.069 Uiso 1 1 calc R . .
C14 C 0.36168(18) 0.7275(5) 0.0324(3) 0.0860(12) Uani 1 1 d . . .
C15 C 0.02949(18) 0.3604(6) -0.0518(2) 0.0742(9) Uani 1 1 d . . .
H15 H 0.0236 0.2331 -0.0430 0.089 Uiso 1 1 calc R . .
C16 C 0.0002(2) 0.4387(7) -0.1170(3) 0.0968(13) Uani 1 1 d . . .
H16 H -0.0255 0.3655 -0.1509 0.116 Uiso 1 1 calc R . .
C17 C 0.0095(3) 0.6230(8) -0.1305(3) 0.1049(14) Uani 1 1 d . . .
H17 H -0.0099 0.6788 -0.1739 0.126 Uiso 1 1 calc R . .
C18 C 0.0484(2) 0.7287(7) -0.0789(3) 0.0950(12) Uani 1 1 d . . .
H18 H 0.0565 0.8552 -0.0877 0.114 Uiso 1 1 calc R . .
C19 C 0.07447(17) 0.6422(5) -0.0148(2) 0.0698(8) Uani 1 1 d . . .
H19 H 0.0992 0.7131 0.0208 0.084 Uiso 1 1 calc R . .
C20 C 0.01624(19) 0.0249(5) 0.1624(2) 0.0741(9) Uani 1 1 d . . .
H20 H 0.0543 -0.0531 0.1551 0.089 Uiso 1 1 calc R . .
C21 C -0.0417(2) -0.0447(6) 0.1983(3) 0.0951(12) Uani 1 1 d . . .
H21 H -0.0426 -0.1680 0.2154 0.114 Uiso 1 1 calc R . .
C22 C -0.0978(2) 0.0682(9) 0.2086(3) 0.1088(16) Uani 1 1 d . . .
H22 H -0.1372 0.0237 0.2336 0.131 Uiso 1 1 calc R . .
C23 C -0.0955(2) 0.2456(8) 0.1821(3) 0.0973(13) Uani 1 1 d . . .
H23 H -0.1338 0.3238 0.1870 0.117 Uiso 1 1 calc R . .
C24 C -0.03598(17) 0.3089(5) 0.1478(2) 0.0734(9) Uani 1 1 d . . .
H24 H -0.0343 0.4323 0.1308 0.088 Uiso 1 1 calc R . .


_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 O3 2.0483(18) . ?
Zn1 O1 2.056(2) . ?
Zn1 N6 2.133(2) . ?
Zn1 N5 2.138(2) . ?
Zn1 N3 2.222(2) . ?
Zn1 N1 2.240(2) . ?
N1 C2 1.337(4) . ?
N1 C6 1.337(4) . ?
N2 C7 1.135(5) . ?
N3 C9 1.334(4) . ?
N3 C13 1.335(3) . ?
N4 C14 1.123(4) . ?
N5 C24 1.328(4) . ?
N5 C20 1.332(4) . ?
N6 C15 1.328(4) . ?
N6 C19 1.332(4) . ?
O1 C1 1.265(4) . ?
O2 C1 1.227(3) . ?
O3 C8 1.262(3) . ?
O4 C8 1.221(3) . ?
C1 C2 1.523(4) . ?
C2 C3 1.379(4) . ?
C3 C4 1.376(5) . ?
C3 H3 0.9300 . ?
C4 C5 1.383(5) . ?
C4 H4 0.9300 . ?
C5 C6 1.376(4) . ?
C5 C7 1.441(5) . ?
C6 H6 0.9300 . ?
C8 C9 1.533(4) . ?
C9 C10 1.378(4) . ?
C10 C11 1.375(5) . ?
C10 H10 0.9300 . ?
C11 C12 1.369(5) . ?
C11 H11 0.9300 . ?
C12 C13 1.387(4) . ?
C12 C14 1.452(5) . ?
C13 H13 0.9300 . ?
C15 C16 1.383(6) . ?
C15 H15 0.9300 . ?
C16 C17 1.350(6) . ?
C16 H16 0.9300 . ?
C17 C18 1.392(7) . ?
C17 H17 0.9300 . ?
C18 C19 1.369(6) . ?
C18 H18 0.9300 . ?
C19 H19 0.9300 . ?
C20 C21 1.371(5) . ?
C20 H20 0.9300 . ?
C21 C22 1.361(6) . ?
C21 H21 0.9300 . ?
C22 C23 1.350(7) . ?
C22 H22 0.9300 . ?
C23 C24 1.369(5) . ?
C23 H23 0.9300 . ?
C24 H24 0.9300 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
O3 Zn1 O1 166.13(9) . . ?
O3 Zn1 N6 97.86(9) . . ?
O1 Zn1 N6 92.45(9) . . ?
O3 Zn1 N5 91.25(8) . . ?
O1 Zn1 N5 96.90(9) . . ?
N6 Zn1 N5 95.92(9) . . ?
O3 Zn1 N3 77.30(8) . . ?
O1 Zn1 N3 93.41(8) . . ?
N6 Zn1 N3 90.61(9) . . ?
N5 Zn1 N3 167.53(9) . . ?
O3 Zn1 N1 91.87(8) . . ?
O1 Zn1 N1 76.94(8) . . ?
N6 Zn1 N1 168.29(9) . . ?
N5 Zn1 N1 90.32(9) . . ?
N3 Zn1 N1 85.18(8) . . ?
C2 N1 C6 118.6(2) . . ?
C2 N1 Zn1 110.51(18) . . ?
C6 N1 Zn1 130.28(19) . . ?
C9 N3 C13 118.9(2) . . ?
C9 N3 Zn1 111.10(17) . . ?
C13 N3 Zn1 129.98(19) . . ?
C24 N5 C20 117.9(3) . . ?
C24 N5 Zn1 118.9(2) . . ?
C20 N5 Zn1 122.9(2) . . ?
C15 N6 C19 118.4(3) . . ?
C15 N6 Zn1 119.8(2) . . ?
C19 N6 Zn1 121.7(2) . . ?
C1 O1 Zn1 119.75(18) . . ?
C8 O3 Zn1 119.56(17) . . ?
O2 C1 O1 126.4(3) . . ?
O2 C1 C2 117.6(3) . . ?
O1 C1 C2 116.0(2) . . ?
N1 C2 C3 121.7(3) . . ?
N1 C2 C1 116.3(2) . . ?
C3 C2 C1 121.9(3) . . ?
C4 C3 C2 119.8(3) . . ?
C4 C3 H3 120.1 . . ?
C2 C3 H3 120.1 . . ?
C3 C4 C5 118.2(3) . . ?
C3 C4 H4 120.9 . . ?
C5 C4 H4 120.9 . . ?
C6 C5 C4 119.1(3) . . ?
C6 C5 C7 121.4(3) . . ?
C4 C5 C7 119.5(3) . . ?
N1 C6 C5 122.5(3) . . ?
N1 C6 H6 118.8 . . ?
C5 C6 H6 118.8 . . ?
N2 C7 C5 177.3(4) . . ?
O4 C8 O3 126.3(3) . . ?
O4 C8 C9 117.6(2) . . ?
O3 C8 C9 116.1(2) . . ?
N3 C9 C10 122.3(3) . . ?
N3 C9 C8 115.9(2) . . ?
C10 C9 C8 121.8(3) . . ?
C11 C10 C9 119.0(3) . . ?
C11 C10 H10 120.5 . . ?
C9 C10 H10 120.5 . . ?
C12 C11 C10 118.8(3) . . ?
C12 C11 H11 120.6 . . ?
C10 C11 H11 120.6 . . ?
C11 C12 C13 119.6(3) . . ?
C11 C12 C14 120.9(3) . . ?
C13 C12 C14 119.5(3) . . ?
N3 C13 C12 121.4(3) . . ?
N3 C13 H13 119.3 . . ?
C12 C13 H13 119.3 . . ?
N4 C14 C12 178.1(5) . . ?
N6 C15 C16 122.5(4) . . ?
N6 C15 H15 118.8 . . ?
C16 C15 H15 118.8 . . ?
C17 C16 C15 118.9(4) . . ?
C17 C16 H16 120.6 . . ?
C15 C16 H16 120.6 . . ?
C16 C17 C18 119.3(4) . . ?
C16 C17 H17 120.4 . . ?
C18 C17 H17 120.4 . . ?
C19 C18 C17 118.5(4) . . ?
C19 C18 H18 120.8 . . ?
C17 C18 H18 120.8 . . ?
N6 C19 C18 122.5(4) . . ?
N6 C19 H19 118.8 . . ?
C18 C19 H19 118.8 . . ?
N5 C20 C21 121.9(4) . . ?
N5 C20 H20 119.1 . . ?
C21 C20 H20 119.1 . . ?
C22 C21 C20 119.4(4) . . ?
C22 C21 H21 120.3 . . ?
C20 C21 H21 120.3 . . ?
C23 C22 C21 119.0(4) . . ?
C23 C22 H22 120.5 . . ?
C21 C22 H22 120.5 . . ?
C22 C23 C24 119.2(4) . . ?
C22 C23 H23 120.4 . . ?
C24 C23 H23 120.4 . . ?
N5 C24 C23 122.6(4) . . ?
N5 C24 H24 118.7 . . ?
C23 C24 H24 118.7 . . ?

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
O3 Zn1 N1 C2 167.74(17) . . . . ?
O1 Zn1 N1 C2 -3.99(17) . . . . ?
N6 Zn1 N1 C2 21.4(5) . . . . ?
N5 Zn1 N1 C2 -101.00(18) . . . . ?
N3 Zn1 N1 C2 90.65(18) . . . . ?
O3 Zn1 N1 C6 -3.2(2) . . . . ?
O1 Zn1 N1 C6 -174.9(3) . . . . ?
N6 Zn1 N1 C6 -149.5(4) . . . . ?
N5 Zn1 N1 C6 88.0(2) . . . . ?
N3 Zn1 N1 C6 -80.3(2) . . . . ?
O3 Zn1 N3 C9 -1.76(18) . . . . ?
O1 Zn1 N3 C9 167.82(19) . . . . ?
N6 Zn1 N3 C9 -99.68(19) . . . . ?
N5 Zn1 N3 C9 22.0(6) . . . . ?
N1 Zn1 N3 C9 91.26(19) . . . . ?
O3 Zn1 N3 C13 -179.3(3) . . . . ?
O1 Zn1 N3 C13 -9.8(3) . . . . ?
N6 Zn1 N3 C13 82.7(3) . . . . ?
N5 Zn1 N3 C13 -155.5(4) . . . . ?
N1 Zn1 N3 C13 -86.3(3) . . . . ?
O3 Zn1 N5 C24 -148.6(3) . . . . ?
O1 Zn1 N5 C24 42.6(3) . . . . ?
N6 Zn1 N5 C24 -50.6(3) . . . . ?
N3 Zn1 N5 C24 -171.8(4) . . . . ?
N1 Zn1 N5 C24 119.5(3) . . . . ?
O3 Zn1 N5 C20 38.3(3) . . . . ?
O1 Zn1 N5 C20 -130.5(3) . . . . ?
N6 Zn1 N5 C20 136.3(3) . . . . ?
N3 Zn1 N5 C20 15.1(6) . . . . ?
N1 Zn1 N5 C20 -53.6(3) . . . . ?
O3 Zn1 N6 C15 36.2(3) . . . . ?
O1 Zn1 N6 C15 -153.1(2) . . . . ?
N5 Zn1 N6 C15 -55.9(3) . . . . ?
N3 Zn1 N6 C15 113.5(2) . . . . ?
N1 Zn1 N6 C15 -177.8(4) . . . . ?
O3 Zn1 N6 C19 -140.3(2) . . . . ?
O1 Zn1 N6 C19 30.4(3) . . . . ?
N5 Zn1 N6 C19 127.6(2) . . . . ?
N3 Zn1 N6 C19 -63.0(2) . . . . ?
N1 Zn1 N6 C19 5.7(6) . . . . ?
O3 Zn1 O1 C1 -37.2(5) . . . . ?
N6 Zn1 O1 C1 -175.3(2) . . . . ?
N5 Zn1 O1 C1 88.4(2) . . . . ?
N3 Zn1 O1 C1 -84.5(2) . . . . ?
N1 Zn1 O1 C1 -0.3(2) . . . . ?
O1 Zn1 O3 C8 -45.8(5) . . . . ?
N6 Zn1 O3 C8 91.9(2) . . . . ?
N5 Zn1 O3 C8 -172.0(2) . . . . ?
N3 Zn1 O3 C8 3.0(2) . . . . ?
N1 Zn1 O3 C8 -81.6(2) . . . . ?
Zn1 O1 C1 O2 -177.0(2) . . . . ?
Zn1 O1 C1 C2 4.2(3) . . . . ?
C6 N1 C2 C3 0.3(4) . . . . ?
Zn1 N1 C2 C3 -171.8(2) . . . . ?
C6 N1 C2 C1 179.3(2) . . . . ?
Zn1 N1 C2 C1 7.2(3) . . . . ?
O2 C1 C2 N1 173.2(2) . . . . ?
O1 C1 C2 N1 -7.9(4) . . . . ?
O2 C1 C2 C3 -7.8(4) . . . . ?
O1 C1 C2 C3 171.1(3) . . . . ?
N1 C2 C3 C4 1.1(5) . . . . ?
C1 C2 C3 C4 -177.8(3) . . . . ?
C2 C3 C4 C5 -1.2(5) . . . . ?
C3 C4 C5 C6 0.0(5) . . . . ?
C3 C4 C5 C7 177.5(3) . . . . ?
C2 N1 C6 C5 -1.6(4) . . . . ?
Zn1 N1 C6 C5 168.8(2) . . . . ?
C4 C5 C6 N1 1.4(4) . . . . ?
C7 C5 C6 N1 -176.0(3) . . . . ?
Zn1 O3 C8 O4 174.4(3) . . . . ?
Zn1 O3 C8 C9 -3.6(3) . . . . ?
C13 N3 C9 C10 -0.7(4) . . . . ?
Zn1 N3 C9 C10 -178.6(2) . . . . ?
C13 N3 C9 C8 178.5(2) . . . . ?
Zn1 N3 C9 C8 0.6(3) . . . . ?
O4 C8 C9 N3 -176.4(3) . . . . ?
O3 C8 C9 N3 1.8(4) . . . . ?
O4 C8 C9 C10 2.8(4) . . . . ?
O3 C8 C9 C10 -178.9(3) . . . . ?
N3 C9 C10 C11 0.0(5) . . . . ?
C8 C9 C10 C11 -179.2(3) . . . . ?
C9 C10 C11 C12 0.7(6) . . . . ?
C10 C11 C12 C13 -0.7(6) . . . . ?
C10 C11 C12 C14 177.3(4) . . . . ?
C9 N3 C13 C12 0.8(4) . . . . ?
Zn1 N3 C13 C12 178.2(2) . . . . ?
C11 C12 C13 N3 0.0(5) . . . . ?
C14 C12 C13 N3 -178.1(3) . . . . ?
C19 N6 C15 C16 -0.6(5) . . . . ?
Zn1 N6 C15 C16 -177.2(3) . . . . ?
N6 C15 C16 C17 0.9(7) . . . . ?
C15 C16 C17 C18 0.3(7) . . . . ?
C16 C17 C18 C19 -1.7(7) . . . . ?
C15 N6 C19 C18 -1.0(5) . . . . ?
Zn1 N6 C19 C18 175.6(3) . . . . ?
C17 C18 C19 N6 2.1(6) . . . . ?
C24 N5 C20 C21 -1.1(6) . . . . ?
Zn1 N5 C20 C21 172.0(3) . . . . ?
N5 C20 C21 C22 0.6(7) . . . . ?
C20 C21 C22 C23 1.1(7) . . . . ?
C21 C22 C23 C24 -2.1(8) . . . . ?
C20 N5 C24 C23 0.1(6) . . . . ?
Zn1 N5 C24 C23 -173.4(3) . . . . ?
C22 C23 C24 N5 1.6(7) . . . . ?

_diffrn_measured_fraction_theta_max 0.999
_diffrn_reflns_theta_full        27.48
_diffrn_measured_fraction_theta_full 0.999
_refine_diff_density_max         0.355
_refine_diff_density_min         -0.218
_refine_diff_density_rms         0.036
####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_10
_database_code_depnum_ccdc_archive 'CCDC 1480535'
_audit_update_record             
;
2016-05-17 deposited with the CCDC.
2016-12-07 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C26 H14 N6 O4 Zn, C7 H8, 2(C H4 O)'
_chemical_formula_sum            'C35 H30 N6 O6 Zn'
_chemical_formula_weight         696.02

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'

_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 21/c'
_space_group_name_Hall           '-P 2ybc'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;

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

_cell_length_a                   13.0350(3)
_cell_length_b                   29.0574(7)
_cell_length_c                   20.4786(5)
_cell_angle_alpha                90
_cell_angle_beta                 118.529(2)
_cell_angle_gamma                90
_cell_volume                     6814.7(3)
_cell_formula_units_Z            8
_cell_measurement_temperature    150(2)
_cell_measurement_reflns_used    14565
_cell_measurement_theta_min      2.6577
_cell_measurement_theta_max      30.3772

_exptl_crystal_description       prism
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.357
_exptl_crystal_F_000             2880
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.600
_exptl_crystal_size_mid          0.300
_exptl_crystal_size_min          0.250
_exptl_absorpt_coefficient_mu    0.774
_shelx_estimated_absorpt_T_min   0.654
_shelx_estimated_absorpt_T_max   0.830
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.55006
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_process_details   '(CrysAlis PRO; Agilent, 2013)'

_exptl_special_details           
;
374 frames in 4 runs of ω scans. Crystal-detector distance = 55.0 mm. 
;
_diffrn_ambient_temperature      150(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'SuperNova (Mo) X-ray Source'
_diffrn_radiation_monochromator  Mirror
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, Atlas'
_diffrn_measurement_method       'ω scans'
_diffrn_detector_area_resol_mean 10.4933
_diffrn_reflns_number            62321
_diffrn_reflns_av_unetI/netI     0.0327
_diffrn_reflns_av_R_equivalents  0.0334
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_k_min       -37
_diffrn_reflns_limit_k_max       37
_diffrn_reflns_limit_l_min       -26
_diffrn_reflns_limit_l_max       26
_diffrn_reflns_theta_min         2.663
_diffrn_reflns_theta_max         27.485
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measured_fraction_theta_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_point_group_measured_fraction_full 0.998
_reflns_number_total             15622
_reflns_number_gt                8344
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;


_computing_data_collection       'CrysAlis PRO (Agilent, 2013)'
_computing_cell_refinement       'CrysAlis PRO (Agilent, 2013)'
_computing_data_reduction        'CrysAlis PRO (Agilent, 2013)'
_computing_structure_solution    'SIR97 (Altomare et al., 1999)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2015)'
_computing_molecular_graphics    
'ORTEP-3 for Windows version 2.02 (Farrugia, 2008)'
_computing_publication_material  'WinGX publication routines (Farrugia, 1999)'
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0787P)²+7.4633P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         15622
_refine_ls_number_parameters     888
_refine_ls_number_restraints     4
_refine_ls_R_factor_all          0.0994
_refine_ls_R_factor_gt           0.0585
_refine_ls_wR_factor_ref         0.2059
_refine_ls_wR_factor_gt          0.1756
_refine_ls_goodness_of_fit_ref   1.072
_refine_ls_restrained_S_all      1.074
_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_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Zn1 Zn 0.00332(2) 0.11100(2) 0.74917(2) 0.02067(12) Uani 1 1 d . . . . .
Zn2 Zn 0.50105(2) 0.13906(2) 0.74839(2) 0.02053(12) Uani 1 1 d . . . . .
N1 N -0.1261(2) 0.15592(8) 0.66402(13) 0.0217(5) Uani 1 1 d . . . . .
N2 N -0.4993(2) 0.22577(11) 0.58666(16) 0.0378(7) Uani 1 1 d . . . . .
N3 N 0.1266(2) 0.15968(8) 0.83080(13) 0.0212(5) Uani 1 1 d . . . . .
N4 N 0.4905(3) 0.23645(11) 0.90406(17) 0.0431(8) Uani 1 1 d . . . . .
N5 N 0.1233(2) 0.05471(9) 0.80179(14) 0.0268(6) Uani 1 1 d . . . . .
N6 N -0.1050(2) 0.05092(9) 0.70302(14) 0.0254(6) Uani 1 1 d . . . . .
N7 N 0.6282(2) 0.09264(8) 0.83289(13) 0.0211(5) Uani 1 1 d . . . . .
N8 N 0.9920(3) 0.01588(11) 0.90518(17) 0.0429(8) Uani 1 1 d . . . . .
N9 N 0.37540(19) 0.09171(8) 0.66620(13) 0.0206(5) Uani 1 1 d . . . . .
N10 N 0.0016(2) 0.02199(10) 0.58888(16) 0.0375(7) Uani 1 1 d . . . . .
N11 N 0.3858(2) 0.19721(9) 0.69738(14) 0.0246(6) Uani 1 1 d . . . . .
N12 N 0.6144(2) 0.19746(9) 0.79585(14) 0.0262(6) Uani 1 1 d . . . . .
O1 O 0.07469(17) 0.12322(7) 0.67949(11) 0.0248(5) Uani 1 1 d . . . . .
O2 O 0.0343(2) 0.14607(9) 0.56579(13) 0.0352(6) Uani 1 1 d . . . . .
O3 O -0.06829(17) 0.12225(7) 0.81835(11) 0.0254(5) Uani 1 1 d . . . . .
O4 O -0.0298(2) 0.14625(9) 0.93095(13) 0.0374(6) Uani 1 1 d . . . . .
O5 O 0.43181(17) 0.12900(7) 0.81931(11) 0.0259(5) Uani 1 1 d . . . . .
O6 O 0.4746(2) 0.10793(9) 0.93409(13) 0.0362(6) Uani 1 1 d . . . . .
O7 O 0.57375(17) 0.12565(7) 0.67997(11) 0.0243(5) Uani 1 1 d . . . . .
O8 O 0.5378(2) 0.09908(9) 0.56905(13) 0.0369(6) Uani 1 1 d . . . . .
O9 O 0.8833(3) 0.13089(11) 0.41961(15) 0.0735(11) Uani 1 1 d . . . . .
H9 H 0.9317 0.1347 0.4647 0.110 Uiso 1 1 calc R U . . .
O10 O 0.6251(3) 0.12218(10) 0.08067(15) 0.0724(10) Uani 1 1 d . . . . .
H10A H 0.5731 0.1167 0.0370 0.109 Uiso 1 1 calc R U . . .
C1 C 0.0123(3) 0.14284(11) 0.61798(18) 0.0252(7) Uani 1 1 d . . . . .
C2 C -0.1004(2) 0.16465(10) 0.60902(16) 0.0224(6) Uani 1 1 d . . . . .
C3 C -0.1714(3) 0.19110(12) 0.54805(18) 0.0333(8) Uani 1 1 d . . . . .
H3 H -0.1495 0.1977 0.5109 0.040 Uiso 1 1 calc R U . . .
C4 C -0.2753(3) 0.20797(12) 0.54176(18) 0.0338(8) Uani 1 1 d . . . . .
H4 H -0.3263 0.2260 0.5001 0.041 Uiso 1 1 calc R U . . .
C5 C -0.3032(3) 0.19784(11) 0.59784(17) 0.0253(7) Uani 1 1 d . . . . .
C6 C -0.2252(2) 0.17212(10) 0.65884(17) 0.0235(6) Uani 1 1 d . . . . .
H6 H -0.2432 0.1660 0.6978 0.028 Uiso 1 1 calc R U . . .
C7 C -0.4125(3) 0.21300(11) 0.59228(18) 0.0299(7) Uani 1 1 d . . . . .
C8 C -0.0075(3) 0.14306(10) 0.87868(18) 0.0239(7) Uani 1 1 d . . . . .
C9 C 0.1028(2) 0.16635(10) 0.88715(16) 0.0220(6) Uani 1 1 d . . . . .
C10 C 0.1743(3) 0.19235(12) 0.94901(18) 0.0303(7) Uani 1 1 d . . . . .
H10 H 0.1545 0.1970 0.9875 0.036 Uiso 1 1 calc R U . . .
C11 C 0.2754(3) 0.21156(11) 0.95407(18) 0.0308(7) Uani 1 1 d . . . . .
H11 H 0.3262 0.2294 0.9960 0.037 Uiso 1 1 calc R U . . .
C12 C 0.3001(2) 0.20393(11) 0.89609(17) 0.0249(7) Uani 1 1 d . . . . .
C13 C 0.2234(2) 0.17806(10) 0.83500(17) 0.0239(7) Uani 1 1 d . . . . .
H13 H 0.2404 0.1733 0.7953 0.029 Uiso 1 1 calc R U . . .
C14 C 0.4059(3) 0.22199(12) 0.89956(18) 0.0311(7) Uani 1 1 d . . . . .
C15 C 0.2370(3) 0.05707(12) 0.85034(19) 0.0352(8) Uani 1 1 d . . . . .
H15 H 0.2717 0.0865 0.8660 0.042 Uiso 1 1 calc R U . . .
C16 C 0.3070(3) 0.01823(13) 0.8790(2) 0.0429(9) Uani 1 1 d . . . . .
H16 H 0.3878 0.0213 0.9132 0.051 Uiso 1 1 calc R U . . .
C17 C 0.2582(3) -0.02443(13) 0.8575(2) 0.0425(9) Uani 1 1 d . . . . .
H17 H 0.3048 -0.0513 0.8764 0.051 Uiso 1 1 calc R U . . .
C18 C 0.1382(3) -0.02821(11) 0.80695(19) 0.0357(8) Uani 1 1 d . . . . .
C19 C 0.0747(3) 0.01244(10) 0.78057(17) 0.0265(7) Uani 1 1 d . . . . .
C20 C -0.0477(3) 0.01050(11) 0.72846(17) 0.0270(7) Uani 1 1 d . . . . .
C21 C -0.1031(3) -0.03245(12) 0.70593(19) 0.0367(8) Uani 1 1 d . . . . .
C22 C -0.2237(3) -0.03246(13) 0.6559(2) 0.0437(9) Uani 1 1 d . . . . .
H22 H -0.2649 -0.0607 0.6394 0.052 Uiso 1 1 calc R U . . .
C23 C -0.2807(3) 0.00808(13) 0.6312(2) 0.0421(9) Uani 1 1 d . . . . .
H23 H -0.3622 0.0084 0.5978 0.051 Uiso 1 1 calc R U . . .
C24 C -0.2188(3) 0.04948(12) 0.65541(19) 0.0332(8) Uani 1 1 d . . . . .
H24 H -0.2596 0.0776 0.6371 0.040 Uiso 1 1 calc R U . . .
C25 C 0.0796(4) -0.07159(13) 0.7829(2) 0.0505(10) Uani 1 1 d . . . . .
H25 H 0.1225 -0.0994 0.8008 0.061 Uiso 1 1 calc R U . . .
C26 C -0.0354(4) -0.07339(13) 0.7352(2) 0.0509(10) Uani 1 1 d . . . . .
H26 H -0.0726 -0.1025 0.7206 0.061 Uiso 1 1 calc R U . . .
C27 C 0.4950(3) 0.10981(10) 0.88100(18) 0.0239(7) Uani 1 1 d . . . . .
C28 C 0.6056(2) 0.08652(10) 0.88945(16) 0.0229(7) Uani 1 1 d . . . . .
C29 C 0.6770(3) 0.06090(12) 0.95122(18) 0.0329(8) Uani 1 1 d . . . . .
H29 H 0.6575 0.0565 0.9900 0.039 Uiso 1 1 calc R U . . .
C30 C 0.7779(3) 0.04155(12) 0.95609(18) 0.0338(8) Uani 1 1 d . . . . .
H30 H 0.8287 0.0237 0.9981 0.041 Uiso 1 1 calc R U . . .
C31 C 0.8026(2) 0.04896(11) 0.89787(18) 0.0261(7) Uani 1 1 d . . . . .
C32 C 0.7252(2) 0.07427(10) 0.83648(17) 0.0242(7) Uani 1 1 d . . . . .
H32 H 0.7412 0.0787 0.7963 0.029 Uiso 1 1 calc R U . . .
C33 C 0.9080(3) 0.03068(12) 0.90150(18) 0.0315(8) Uani 1 1 d . . . . .
C34 C 0.5141(3) 0.10411(11) 0.62024(18) 0.0248(7) Uani 1 1 d . . . . .
C35 C 0.4011(2) 0.08260(10) 0.61132(16) 0.0225(6) Uani 1 1 d . . . . .
C36 C 0.3300(3) 0.05604(12) 0.55033(19) 0.0337(8) Uani 1 1 d . . . . .
H36 H 0.3520 0.0493 0.5133 0.040 Uiso 1 1 calc R U . . .
C37 C 0.2259(3) 0.03930(12) 0.54408(19) 0.0345(8) Uani 1 1 d . . . . .
H37 H 0.1748 0.0213 0.5025 0.041 Uiso 1 1 calc R U . . .
C38 C 0.1983(3) 0.04959(11) 0.60030(17) 0.0256(7) Uani 1 1 d . . . . .
C39 C 0.2761(2) 0.07554(10) 0.66125(17) 0.0229(6) Uani 1 1 d . . . . .
H39 H 0.2581 0.0818 0.7001 0.028 Uiso 1 1 calc R U . . .
C40 C 0.0890(3) 0.03442(11) 0.59510(18) 0.0286(7) Uani 1 1 d . . . . .
C41 C 0.2714(3) 0.19654(12) 0.64907(19) 0.0328(8) Uani 1 1 d . . . . .
H41 H 0.2338 0.1677 0.6319 0.039 Uiso 1 1 calc R U . . .
C42 C 0.2054(3) 0.23684(13) 0.6231(2) 0.0419(9) Uani 1 1 d . . . . .
H42 H 0.1242 0.2352 0.5893 0.050 Uiso 1 1 calc R U . . .
C43 C 0.2585(3) 0.27850(13) 0.6464(2) 0.0435(9) Uani 1 1 d . . . . .
H43 H 0.2144 0.3061 0.6290 0.052 Uiso 1 1 calc R U . . .
C44 C 0.3788(3) 0.28048(12) 0.69630(19) 0.0349(8) Uani 1 1 d . . . . .
C45 C 0.4381(3) 0.23855(10) 0.72065(17) 0.0260(7) Uani 1 1 d . . . . .
C46 C 0.5606(3) 0.23859(11) 0.77265(17) 0.0266(7) Uani 1 1 d . . . . .
C47 C 0.6197(3) 0.28072(12) 0.7965(2) 0.0373(8) Uani 1 1 d . . . . .
C48 C 0.7401(3) 0.27882(14) 0.8464(2) 0.0469(10) Uani 1 1 d . . . . .
H48 H 0.7837 0.3065 0.8638 0.056 Uiso 1 1 calc R U . . .
C49 C 0.7944(3) 0.23746(14) 0.8699(2) 0.0456(10) Uani 1 1 d . . . . .
H49 H 0.8757 0.2360 0.9036 0.055 Uiso 1 1 calc R U . . .
C50 C 0.7287(3) 0.19717(12) 0.84347(19) 0.0361(8) Uani 1 1 d . . . . .
H50 H 0.7669 0.1684 0.8601 0.043 Uiso 1 1 calc R U . . .
C51 C 0.4411(4) 0.32260(13) 0.7227(2) 0.0487(10) Uani 1 1 d . . . . .
H51 H 0.4005 0.3510 0.7067 0.058 Uiso 1 1 calc R U . . .
C52 C 0.5565(4) 0.32284(13) 0.7700(2) 0.0504(10) Uani 1 1 d . . . . .
H52 H 0.5965 0.3514 0.7861 0.061 Uiso 1 1 calc R U . . .
C53 C 0.8978(5) 0.08678(16) 0.3970(3) 0.0801(16) Uani 1 1 d . . . . .
H53A H 0.9026 0.0640 0.4336 0.096 Uiso 1 1 calc R U . . .
H53B H 0.9698 0.0860 0.3931 0.096 Uiso 1 1 calc R U . . .
H53C H 0.8310 0.0796 0.3485 0.096 Uiso 1 1 calc R U . . .
C54 C 0.6066(5) 0.16589(17) 0.1022(3) 0.0838(17) Uani 1 1 d . . . . .
H54A H 0.5334 0.1659 0.1047 0.101 Uiso 1 1 calc R U . . .
H54B H 0.6020 0.1888 0.0657 0.101 Uiso 1 1 calc R U . . .
H54C H 0.6716 0.1736 0.1511 0.101 Uiso 1 1 calc R U . . .
C57 C -0.0304(7) 0.2277(3) 0.2534(4) 0.134(3) Uani 1 1 d . . . . .
H57A H -0.0145 0.2409 0.2151 0.200 Uiso 1 1 calc R U . . .
H57B H -0.0501 0.2524 0.2781 0.200 Uiso 1 1 calc R U . . .
H57C H -0.0960 0.2062 0.2304 0.200 Uiso 1 1 calc R U . . .
C58 C 0.0693(3) 0.20420(10) 0.3062(2) 0.0762(15) Uani 1 1 d G . . . .
C59 C 0.0765(3) 0.19028(10) 0.3732(2) 0.0851(17) Uani 1 1 d G . . . .
H59 H 0.0126 0.1954 0.3825 0.102 Uiso 1 1 calc R U . . .
C60 C 0.1772(4) 0.16894(12) 0.4266(2) 0.111(2) Uani 1 1 d G . . . .
H60 H 0.1821 0.1594 0.4724 0.133 Uiso 1 1 calc R U . . .
C61 C 0.2707(3) 0.16152(12) 0.41303(17) 0.110(2) Uani 1 1 d G . . . .
H61 H 0.3395 0.1469 0.4495 0.132 Uiso 1 1 calc R U . . .
C62 C 0.2634(3) 0.17544(8) 0.3460(2) 0.117(3) Uani 1 1 d G . . . .
H62 H 0.3273 0.1704 0.3367 0.141 Uiso 1 1 calc R U . . .
C63 C 0.1628(3) 0.19678(9) 0.2926(2) 0.0913(19) Uani 1 1 d G . . . .
H63 H 0.1578 0.2063 0.2468 0.110 Uiso 1 1 calc R U . . .
C64 C 0.5243(5) 0.0229(2) 0.2425(3) 0.144(3) Uani 1 1 d G . . . .
H64A H 0.5080 0.0103 0.2810 0.216 Uiso 1 1 calc R U . . .
H64B H 0.5896 0.0446 0.2652 0.216 Uiso 1 1 calc R U . . .
H64C H 0.5447 -0.0022 0.2189 0.216 Uiso 1 1 calc R U . . .
C65 C 0.4238(3) 0.04607(11) 0.1882(2) 0.0702(14) Uani 1 1 d G . . . .
C66 C 0.4142(4) 0.06048(13) 0.1208(3) 0.0846(16) Uani 1 1 d G . . . .
H66 H 0.4778 0.0564 0.1109 0.101 Uiso 1 1 calc R U . . .
C67 C 0.3115(5) 0.08087(12) 0.06785(17) 0.107(2) Uani 1 1 d G . . . .
H67 H 0.3049 0.0907 0.0218 0.128 Uiso 1 1 calc R U . . .
C68 C 0.2185(3) 0.08683(12) 0.0823(3) 0.097(2) Uani 1 1 d G . . . .
H68 H 0.1483 0.1008 0.0461 0.117 Uiso 1 1 calc R U . . .
C69 C 0.2281(3) 0.07242(13) 0.1497(3) 0.106(2) Uani 1 1 d G . . . .
H69 H 0.1645 0.0765 0.1596 0.127 Uiso 1 1 calc R U . . .
C70 C 0.3308(4) 0.05204(12) 0.2027(2) 0.0813(16) Uani 1 1 d G . . . .
H70 H 0.3374 0.0422 0.2488 0.098 Uiso 1 1 calc R U . . .
O12A O 0.5387(13) 0.0532(5) 0.4499(8) 0.114(5) Uani 0.470(15) 1 d D . P A 1
H12A H 0.5159 0.0700 0.4736 0.171 Uiso 0.470(15) 1 d R U P A 1
C56A C 0.6350(12) 0.0770(4) 0.4459(6) 0.084(5) Uani 0.470(15) 1 d D . P A 1
H56A H 0.6060 0.1057 0.4178 0.127 Uiso 0.470(15) 1 calc R U P A 1
H56B H 0.6664 0.0572 0.4209 0.127 Uiso 0.470(15) 1 calc R U P A 1
H56C H 0.6968 0.0840 0.4962 0.127 Uiso 0.470(15) 1 calc R U P A 1
O12B O 0.4788(10) 0.0698(5) 0.4314(5) 0.107(5) Uani 0.530(15) 1 d D . P A 2
H12B H 0.5080 0.0672 0.4777 0.161 Uiso 0.530(15) 1 d R U P A 2
C56B C 0.5519(10) 0.1000(4) 0.4132(5) 0.073(4) Uani 0.530(15) 1 d D . P A 2
H56D H 0.5238 0.0993 0.3595 0.110 Uiso 0.530(15) 1 calc R U P A 2
H56E H 0.6329 0.0892 0.4393 0.110 Uiso 0.530(15) 1 calc R U P A 2
H56F H 0.5478 0.1315 0.4288 0.110 Uiso 0.530(15) 1 calc R U P A 2
O11A O 1.000(2) 0.3168(10) 0.5584(14) 0.098(7) Uani 0.53(3) 1 d D . P B 1
H11A H 1.0276 0.3338 0.5371 0.147 Uiso 0.53(3) 1 calc R U P B 1
C55A C 0.927(2) 0.3439(9) 0.5793(11) 0.101(9) Uani 0.53(3) 1 d D . P B 1
H55A H 0.9545 0.3404 0.6327 0.151 Uiso 0.53(3) 1 calc R U P B 1
H55B H 0.8463 0.3333 0.5514 0.151 Uiso 0.53(3) 1 calc R U P B 1
H55C H 0.9316 0.3764 0.5680 0.151 Uiso 0.53(3) 1 calc R U P B 1
O11B O 0.9681(17) 0.3017(6) 0.5439(15) 0.072(4) Uani 0.47(3) 1 d D . P B 2
H11B H 0.9815 0.3165 0.5135 0.109 Uiso 0.47(3) 1 calc R U P B 2
C55B C 0.8714(15) 0.3229(6) 0.5492(9) 0.088(6) Uani 0.47(3) 1 d D . P B 2
H55D H 0.8956 0.3530 0.5732 0.133 Uiso 0.47(3) 1 calc R U P B 2
H55E H 0.8484 0.3031 0.5788 0.133 Uiso 0.47(3) 1 calc R U P B 2
H55F H 0.8052 0.3267 0.4993 0.133 Uiso 0.47(3) 1 calc R U P B 2


_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 2.061(2) . ?
Zn1 O1 2.073(2) . ?
Zn1 N6 2.159(3) . ?
Zn1 N5 2.162(2) . ?
Zn1 N1 2.186(2) . ?
Zn1 N3 2.193(2) . ?
Zn2 O5 2.064(2) . ?
Zn2 O7 2.069(2) . ?
Zn2 N12 2.153(3) . ?
Zn2 N11 2.169(2) . ?
Zn2 N9 2.185(2) . ?
Zn2 N7 2.196(2) . ?
N1 C6 1.331(4) . ?
N1 C2 1.343(4) . ?
N2 C7 1.144(4) . ?
N3 C13 1.336(4) . ?
N3 C9 1.344(4) . ?
N4 C14 1.142(4) . ?
N5 C15 1.335(4) . ?
N5 C19 1.355(4) . ?
N6 C24 1.331(4) . ?
N6 C20 1.355(4) . ?
N7 C28 1.337(4) . ?
N7 C32 1.341(4) . ?
N8 C33 1.145(4) . ?
N9 C39 1.334(4) . ?
N9 C35 1.344(4) . ?
N10 C40 1.143(4) . ?
N11 C41 1.339(4) . ?
N11 C45 1.351(4) . ?
N12 C50 1.335(4) . ?
N12 C46 1.352(4) . ?
O1 C1 1.263(4) . ?
O2 C1 1.235(4) . ?
O3 C8 1.259(4) . ?
O4 C8 1.240(4) . ?
O5 C27 1.261(4) . ?
O6 C27 1.237(4) . ?
O7 C34 1.258(4) . ?
O8 C34 1.234(4) . ?
O9 C53 1.406(5) . ?
O9 H9 0.8400 . ?
O10 C54 1.402(5) . ?
O10 H10A 0.8400 . ?
C1 C2 1.529(4) . ?
C2 C3 1.379(4) . ?
C3 C4 1.388(4) . ?
C3 H3 0.9500 . ?
C4 C5 1.392(5) . ?
C4 H4 0.9500 . ?
C5 C6 1.393(4) . ?
C5 C7 1.442(4) . ?
C6 H6 0.9500 . ?
C8 C9 1.522(4) . ?
C9 C10 1.384(4) . ?
C10 C11 1.389(4) . ?
C10 H10 0.9500 . ?
C11 C12 1.388(5) . ?
C11 H11 0.9500 . ?
C12 C13 1.391(4) . ?
C12 C14 1.445(4) . ?
C13 H13 0.9500 . ?
C15 C16 1.393(5) . ?
C15 H15 0.9500 . ?
C16 C17 1.367(5) . ?
C16 H16 0.9500 . ?
C17 C18 1.408(5) . ?
C17 H17 0.9500 . ?
C18 C19 1.395(4) . ?
C18 C25 1.434(5) . ?
C19 C20 1.436(5) . ?
C20 C21 1.405(4) . ?
C21 C22 1.408(5) . ?
C21 C26 1.432(5) . ?
C22 C23 1.355(5) . ?
C22 H22 0.9500 . ?
C23 C24 1.401(5) . ?
C23 H23 0.9500 . ?
C24 H24 0.9500 . ?
C25 C26 1.343(6) . ?
C25 H25 0.9500 . ?
C26 H26 0.9500 . ?
C27 C28 1.526(4) . ?
C28 C29 1.377(4) . ?
C29 C30 1.390(4) . ?
C29 H29 0.9500 . ?
C30 C31 1.393(5) . ?
C30 H30 0.9500 . ?
C31 C32 1.389(4) . ?
C31 C33 1.441(4) . ?
C32 H32 0.9500 . ?
C34 C35 1.529(4) . ?
C35 C36 1.382(4) . ?
C36 C37 1.389(4) . ?
C36 H36 0.9500 . ?
C37 C38 1.393(5) . ?
C37 H37 0.9500 . ?
C38 C39 1.395(4) . ?
C38 C40 1.446(4) . ?
C39 H39 0.9500 . ?
C41 C42 1.399(5) . ?
C41 H41 0.9500 . ?
C42 C43 1.362(5) . ?
C42 H42 0.9500 . ?
C43 C44 1.406(5) . ?
C43 H43 0.9500 . ?
C44 C45 1.401(4) . ?
C44 C51 1.425(5) . ?
C45 C46 1.436(5) . ?
C46 C47 1.404(4) . ?
C47 C48 1.407(5) . ?
C47 C52 1.430(5) . ?
C48 C49 1.361(6) . ?
C48 H48 0.9500 . ?
C49 C50 1.398(5) . ?
C49 H49 0.9500 . ?
C50 H50 0.9500 . ?
C51 C52 1.345(7) . ?
C51 H51 0.9500 . ?
C52 H52 0.9500 . ?
C53 H53A 0.9800 . ?
C53 H53B 0.9800 . ?
C53 H53C 0.9800 . ?
C54 H54A 0.9800 . ?
C54 H54B 0.9800 . ?
C54 H54C 0.9800 . ?
C57 C58 1.407(7) . ?
C57 H57A 0.9800 . ?
C57 H57B 0.9800 . ?
C57 H57C 0.9800 . ?
C58 C59 1.3900 . ?
C58 C63 1.3900 . ?
C59 C60 1.3900 . ?
C59 H59 0.9500 . ?
C60 C61 1.3900 . ?
C60 H60 0.9500 . ?
C61 C62 1.3900 . ?
C61 H61 0.9500 . ?
C62 C63 1.3900 . ?
C62 H62 0.9500 . ?
C63 H63 0.9500 . ?
C64 C65 1.419(6) . ?
C64 H64A 0.9800 . ?
C64 H64B 0.9800 . ?
C64 H64C 0.9800 . ?
C65 C66 1.3900 . ?
C65 C70 1.3900 . ?
C66 C67 1.3900 . ?
C66 H66 0.9500 . ?
C67 C68 1.3900 . ?
C67 H67 0.9500 . ?
C68 C69 1.3900 . ?
C68 H68 0.9500 . ?
C69 C70 1.3900 . ?
C69 H69 0.9500 . ?
C70 H70 0.9500 . ?
O12A C56A 1.471(5) . ?
O12A H12A 0.8367 . ?
C56A H56A 0.9800 . ?
C56A H56B 0.9800 . ?
C56A H56C 0.9800 . ?
O12B C56B 1.466(5) . ?
O12B H12B 0.8400 . ?
C56B H56D 0.9800 . ?
C56B H56E 0.9800 . ?
C56B H56F 0.9800 . ?
O11A C55A 1.452(5) . ?
O11A H11A 0.8400 . ?
C55A H55A 0.9800 . ?
C55A H55B 0.9800 . ?
C55A H55C 0.9800 . ?
O11B C55B 1.452(5) . ?
O11B H11B 0.8400 . ?
C55B H55D 0.9800 . ?
C55B H55E 0.9800 . ?
C55B H55F 0.9800 . ?

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 O1 161.01(10) . . ?
O3 Zn1 N6 90.74(9) . . ?
O1 Zn1 N6 104.60(9) . . ?
O3 Zn1 N5 103.57(9) . . ?
O1 Zn1 N5 90.98(9) . . ?
N6 Zn1 N5 76.85(10) . . ?
O3 Zn1 N1 91.34(9) . . ?
O1 Zn1 N1 77.15(9) . . ?
N6 Zn1 N1 92.26(9) . . ?
N5 Zn1 N1 161.48(10) . . ?
O3 Zn1 N3 77.35(9) . . ?
O1 Zn1 N3 90.46(9) . . ?
N6 Zn1 N3 160.57(10) . . ?
N5 Zn1 N3 90.91(9) . . ?
N1 Zn1 N3 103.18(10) . . ?
O5 Zn2 O7 160.96(10) . . ?
O5 Zn2 N12 103.32(9) . . ?
O7 Zn2 N12 90.95(9) . . ?
O5 Zn2 N11 90.81(9) . . ?
O7 Zn2 N11 104.86(9) . . ?
N12 Zn2 N11 76.79(11) . . ?
O5 Zn2 N9 91.95(9) . . ?
O7 Zn2 N9 77.12(9) . . ?
N12 Zn2 N9 160.78(10) . . ?
N11 Zn2 N9 91.58(9) . . ?
O5 Zn2 N7 77.17(9) . . ?
O7 Zn2 N7 90.02(9) . . ?
N12 Zn2 N7 91.79(9) . . ?
N11 Zn2 N7 161.20(10) . . ?
N9 Zn2 N7 103.08(10) . . ?
C6 N1 C2 119.2(3) . . ?
C6 N1 Zn1 128.6(2) . . ?
C2 N1 Zn1 112.03(19) . . ?
C13 N3 C9 119.0(3) . . ?
C13 N3 Zn1 129.3(2) . . ?
C9 N3 Zn1 111.23(19) . . ?
C15 N5 C19 117.9(3) . . ?
C15 N5 Zn1 127.9(2) . . ?
C19 N5 Zn1 114.20(19) . . ?
C24 N6 C20 118.1(3) . . ?
C24 N6 Zn1 127.8(2) . . ?
C20 N6 Zn1 114.0(2) . . ?
C28 N7 C32 119.5(3) . . ?
C28 N7 Zn2 111.61(18) . . ?
C32 N7 Zn2 128.7(2) . . ?
C39 N9 C35 119.2(3) . . ?
C39 N9 Zn2 128.6(2) . . ?
C35 N9 Zn2 111.93(18) . . ?
C41 N11 C45 118.0(3) . . ?
C41 N11 Zn2 128.0(2) . . ?
C45 N11 Zn2 113.98(19) . . ?
C50 N12 C46 118.2(3) . . ?
C50 N12 Zn2 127.6(2) . . ?
C46 N12 Zn2 114.16(19) . . ?
C1 O1 Zn1 118.52(19) . . ?
C8 O3 Zn1 118.13(19) . . ?
C27 O5 Zn2 118.14(19) . . ?
C34 O7 Zn2 118.82(19) . . ?
C53 O9 H9 109.5 . . ?
C54 O10 H10A 109.5 . . ?
O2 C1 O1 126.3(3) . . ?
O2 C1 C2 118.2(3) . . ?
O1 C1 C2 115.5(3) . . ?
N1 C2 C3 122.4(3) . . ?
N1 C2 C1 115.6(3) . . ?
C3 C2 C1 122.0(3) . . ?
C2 C3 C4 118.9(3) . . ?
C2 C3 H3 120.5 . . ?
C4 C3 H3 120.5 . . ?
C3 C4 C5 118.5(3) . . ?
C3 C4 H4 120.8 . . ?
C5 C4 H4 120.8 . . ?
C4 C5 C6 119.1(3) . . ?
C4 C5 C7 120.5(3) . . ?
C6 C5 C7 120.4(3) . . ?
N1 C6 C5 121.8(3) . . ?
N1 C6 H6 119.1 . . ?
C5 C6 H6 119.1 . . ?
N2 C7 C5 178.4(4) . . ?
O4 C8 O3 125.9(3) . . ?
O4 C8 C9 117.8(3) . . ?
O3 C8 C9 116.3(3) . . ?
N3 C9 C10 122.3(3) . . ?
N3 C9 C8 115.5(3) . . ?
C10 C9 C8 122.2(3) . . ?
C9 C10 C11 119.2(3) . . ?
C9 C10 H10 120.4 . . ?
C11 C10 H10 120.4 . . ?
C12 C11 C10 118.1(3) . . ?
C12 C11 H11 120.9 . . ?
C10 C11 H11 120.9 . . ?
C11 C12 C13 119.7(3) . . ?
C11 C12 C14 120.4(3) . . ?
C13 C12 C14 119.9(3) . . ?
N3 C13 C12 121.7(3) . . ?
N3 C13 H13 119.2 . . ?
C12 C13 H13 119.2 . . ?
N4 C14 C12 178.4(4) . . ?
N5 C15 C16 122.9(3) . . ?
N5 C15 H15 118.6 . . ?
C16 C15 H15 118.6 . . ?
C17 C16 C15 119.3(3) . . ?
C17 C16 H16 120.4 . . ?
C15 C16 H16 120.4 . . ?
C16 C17 C18 119.4(3) . . ?
C16 C17 H17 120.3 . . ?
C18 C17 H17 120.3 . . ?
C19 C18 C17 117.6(3) . . ?
C19 C18 C25 119.4(3) . . ?
C17 C18 C25 122.9(3) . . ?
N5 C19 C18 122.9(3) . . ?
N5 C19 C20 117.2(2) . . ?
C18 C19 C20 119.9(3) . . ?
N6 C20 C21 122.8(3) . . ?
N6 C20 C19 117.7(2) . . ?
C21 C20 C19 119.6(3) . . ?
C20 C21 C22 117.4(3) . . ?
C20 C21 C26 118.9(3) . . ?
C22 C21 C26 123.8(3) . . ?
C23 C22 C21 119.6(3) . . ?
C23 C22 H22 120.2 . . ?
C21 C22 H22 120.2 . . ?
C22 C23 C24 119.6(3) . . ?
C22 C23 H23 120.2 . . ?
C24 C23 H23 120.2 . . ?
N6 C24 C23 122.6(3) . . ?
N6 C24 H24 118.7 . . ?
C23 C24 H24 118.7 . . ?
C26 C25 C18 120.7(3) . . ?
C26 C25 H25 119.7 . . ?
C18 C25 H25 119.7 . . ?
C25 C26 C21 121.6(3) . . ?
C25 C26 H26 119.2 . . ?
C21 C26 H26 119.2 . . ?
O6 C27 O5 126.0(3) . . ?
O6 C27 C28 117.9(3) . . ?
O5 C27 C28 116.0(3) . . ?
N7 C28 C29 122.4(3) . . ?
N7 C28 C27 115.5(3) . . ?
C29 C28 C27 122.1(3) . . ?
C28 C29 C30 119.1(3) . . ?
C28 C29 H29 120.5 . . ?
C30 C29 H29 120.5 . . ?
C29 C30 C31 118.3(3) . . ?
C29 C30 H30 120.8 . . ?
C31 C30 H30 120.8 . . ?
C32 C31 C30 119.4(3) . . ?
C32 C31 C33 120.3(3) . . ?
C30 C31 C33 120.2(3) . . ?
N7 C32 C31 121.2(3) . . ?
N7 C32 H32 119.4 . . ?
C31 C32 H32 119.4 . . ?
N8 C33 C31 179.2(4) . . ?
O8 C34 O7 126.6(3) . . ?
O8 C34 C35 117.9(3) . . ?
O7 C34 C35 115.6(3) . . ?
N9 C35 C36 122.6(3) . . ?
N9 C35 C34 115.5(3) . . ?
C36 C35 C34 121.9(3) . . ?
C35 C36 C37 118.9(3) . . ?
C35 C36 H36 120.6 . . ?
C37 C36 H36 120.6 . . ?
C36 C37 C38 118.4(3) . . ?
C36 C37 H37 120.8 . . ?
C38 C37 H37 120.8 . . ?
C37 C38 C39 119.4(3) . . ?
C37 C38 C40 120.5(3) . . ?
C39 C38 C40 120.0(3) . . ?
N9 C39 C38 121.5(3) . . ?
N9 C39 H39 119.2 . . ?
C38 C39 H39 119.2 . . ?
N10 C40 C38 178.0(4) . . ?
N11 C41 C42 122.3(3) . . ?
N11 C41 H41 118.9 . . ?
C42 C41 H41 118.9 . . ?
C43 C42 C41 119.6(3) . . ?
C43 C42 H42 120.2 . . ?
C41 C42 H42 120.2 . . ?
C42 C43 C44 119.6(3) . . ?
C42 C43 H43 120.2 . . ?
C44 C43 H43 120.2 . . ?
C45 C44 C43 117.2(3) . . ?
C45 C44 C51 119.6(3) . . ?
C43 C44 C51 123.1(3) . . ?
N11 C45 C44 123.3(3) . . ?
N11 C45 C46 117.2(2) . . ?
C44 C45 C46 119.5(3) . . ?
N12 C46 C47 122.9(3) . . ?
N12 C46 C45 117.8(2) . . ?
C47 C46 C45 119.3(3) . . ?
C46 C47 C48 117.1(3) . . ?
C46 C47 C52 119.6(3) . . ?
C48 C47 C52 123.4(3) . . ?
C49 C48 C47 120.2(3) . . ?
C49 C48 H48 119.9 . . ?
C47 C48 H48 119.9 . . ?
C48 C49 C50 118.9(3) . . ?
C48 C49 H49 120.5 . . ?
C50 C49 H49 120.5 . . ?
N12 C50 C49 122.8(3) . . ?
N12 C50 H50 118.6 . . ?
C49 C50 H50 118.6 . . ?
C52 C51 C44 121.1(3) . . ?
C52 C51 H51 119.5 . . ?
C44 C51 H51 119.5 . . ?
C51 C52 C47 120.8(3) . . ?
C51 C52 H52 119.6 . . ?
C47 C52 H52 119.6 . . ?
O9 C53 H53A 109.5 . . ?
O9 C53 H53B 109.5 . . ?
H53A C53 H53B 109.5 . . ?
O9 C53 H53C 109.5 . . ?
H53A C53 H53C 109.5 . . ?
H53B C53 H53C 109.5 . . ?
O10 C54 H54A 109.5 . . ?
O10 C54 H54B 109.5 . . ?
H54A C54 H54B 109.5 . . ?
O10 C54 H54C 109.5 . . ?
H54A C54 H54C 109.5 . . ?
H54B C54 H54C 109.5 . . ?
C58 C57 H57A 109.5 . . ?
C58 C57 H57B 109.5 . . ?
H57A C57 H57B 109.5 . . ?
C58 C57 H57C 109.5 . . ?
H57A C57 H57C 109.5 . . ?
H57B C57 H57C 109.5 . . ?
C59 C58 C63 120.0 . . ?
C59 C58 C57 120.1(4) . . ?
C63 C58 C57 119.8(4) . . ?
C60 C59 C58 120.0 . . ?
C60 C59 H59 120.0 . . ?
C58 C59 H59 120.0 . . ?
C61 C60 C59 120.0 . . ?
C61 C60 H60 120.0 . . ?
C59 C60 H60 120.0 . . ?
C60 C61 C62 120.0 . . ?
C60 C61 H61 120.0 . . ?
C62 C61 H61 120.0 . . ?
C63 C62 C61 120.0 . . ?
C63 C62 H62 120.0 . . ?
C61 C62 H62 120.0 . . ?
C62 C63 C58 120.0 . . ?
C62 C63 H63 120.0 . . ?
C58 C63 H63 120.0 . . ?
C65 C64 H64A 109.5 . . ?
C65 C64 H64B 109.5 . . ?
H64A C64 H64B 109.5 . . ?
C65 C64 H64C 109.5 . . ?
H64A C64 H64C 109.5 . . ?
H64B C64 H64C 109.5 . . ?
C66 C65 C70 120.0 . . ?
C66 C65 C64 122.2(4) . . ?
C70 C65 C64 117.7(4) . . ?
C67 C66 C65 120.0 . . ?
C67 C66 H66 120.0 . . ?
C65 C66 H66 120.0 . . ?
C66 C67 C68 120.0 . . ?
C66 C67 H67 120.0 . . ?
C68 C67 H67 120.0 . . ?
C69 C68 C67 120.0 . . ?
C69 C68 H68 120.0 . . ?
C67 C68 H68 120.0 . . ?
C70 C69 C68 120.0 . . ?
C70 C69 H69 120.0 . . ?
C68 C69 H69 120.0 . . ?
C69 C70 C65 120.0 . . ?
C69 C70 H70 120.0 . . ?
C65 C70 H70 120.0 . . ?
C56A O12A H12A 107.8 . . ?
O12A C56A H56A 109.5 . . ?
O12A C56A H56B 109.5 . . ?
H56A C56A H56B 109.5 . . ?
O12A C56A H56C 109.5 . . ?
H56A C56A H56C 109.5 . . ?
H56B C56A H56C 109.5 . . ?
C56B O12B H12B 110.0 . . ?
O12B C56B H56D 109.5 . . ?
O12B C56B H56E 109.5 . . ?
H56D C56B H56E 109.5 . . ?
O12B C56B H56F 109.5 . . ?
H56D C56B H56F 109.5 . . ?
H56E C56B H56F 109.5 . . ?
C55A O11A H11A 109.5 . . ?
O11A C55A H55A 109.5 . . ?
O11A C55A H55B 109.5 . . ?
H55A C55A H55B 109.5 . . ?
O11A C55A H55C 109.5 . . ?
H55A C55A H55C 109.5 . . ?
H55B C55A H55C 109.5 . . ?
C55B O11B H11B 109.5 . . ?
O11B C55B H55D 109.5 . . ?
O11B C55B H55E 109.5 . . ?
H55D C55B H55E 109.5 . . ?
O11B C55B H55F 109.5 . . ?
H55D C55B H55F 109.5 . . ?
H55E C55B H55F 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
Zn1 O1 C1 O2 -167.8(3) . . . . ?
Zn1 O1 C1 C2 12.6(3) . . . . ?
C6 N1 C2 C3 2.1(4) . . . . ?
Zn1 N1 C2 C3 178.1(3) . . . . ?
C6 N1 C2 C1 -177.3(3) . . . . ?
Zn1 N1 C2 C1 -1.3(3) . . . . ?
O2 C1 C2 N1 173.2(3) . . . . ?
O1 C1 C2 N1 -7.2(4) . . . . ?
O2 C1 C2 C3 -6.2(5) . . . . ?
O1 C1 C2 C3 173.5(3) . . . . ?
N1 C2 C3 C4 -2.4(5) . . . . ?
C1 C2 C3 C4 176.9(3) . . . . ?
C2 C3 C4 C5 0.6(5) . . . . ?
C3 C4 C5 C6 1.4(5) . . . . ?
C3 C4 C5 C7 -177.4(3) . . . . ?
C2 N1 C6 C5 0.1(4) . . . . ?
Zn1 N1 C6 C5 -175.2(2) . . . . ?
C4 C5 C6 N1 -1.8(5) . . . . ?
C7 C5 C6 N1 177.0(3) . . . . ?
Zn1 O3 C8 O4 -168.1(3) . . . . ?
Zn1 O3 C8 C9 12.1(3) . . . . ?
C13 N3 C9 C10 1.2(4) . . . . ?
Zn1 N3 C9 C10 174.1(2) . . . . ?
C13 N3 C9 C8 -178.3(3) . . . . ?
Zn1 N3 C9 C8 -5.4(3) . . . . ?
O4 C8 C9 N3 176.4(3) . . . . ?
O3 C8 C9 N3 -3.9(4) . . . . ?
O4 C8 C9 C10 -3.1(4) . . . . ?
O3 C8 C9 C10 176.6(3) . . . . ?
N3 C9 C10 C11 -1.3(5) . . . . ?
C8 C9 C10 C11 178.2(3) . . . . ?
C9 C10 C11 C12 0.3(5) . . . . ?
C10 C11 C12 C13 0.7(5) . . . . ?
C10 C11 C12 C14 -178.2(3) . . . . ?
C9 N3 C13 C12 -0.1(4) . . . . ?
Zn1 N3 C13 C12 -171.5(2) . . . . ?
C11 C12 C13 N3 -0.8(5) . . . . ?
C14 C12 C13 N3 178.0(3) . . . . ?
C19 N5 C15 C16 0.7(5) . . . . ?
Zn1 N5 C15 C16 -177.9(3) . . . . ?
N5 C15 C16 C17 -0.5(6) . . . . ?
C15 C16 C17 C18 -0.2(6) . . . . ?
C16 C17 C18 C19 0.6(5) . . . . ?
C16 C17 C18 C25 -178.5(4) . . . . ?
C15 N5 C19 C18 -0.2(5) . . . . ?
Zn1 N5 C19 C18 178.6(3) . . . . ?
C15 N5 C19 C20 179.9(3) . . . . ?
Zn1 N5 C19 C20 -1.3(4) . . . . ?
C17 C18 C19 N5 -0.4(5) . . . . ?
C25 C18 C19 N5 178.7(3) . . . . ?
C17 C18 C19 C20 179.5(3) . . . . ?
C25 C18 C19 C20 -1.4(5) . . . . ?
C24 N6 C20 C21 0.8(5) . . . . ?
Zn1 N6 C20 C21 179.1(2) . . . . ?
C24 N6 C20 C19 -179.2(3) . . . . ?
Zn1 N6 C20 C19 -0.9(4) . . . . ?
N5 C19 C20 N6 1.5(5) . . . . ?
C18 C19 C20 N6 -178.4(3) . . . . ?
N5 C19 C20 C21 -178.5(3) . . . . ?
C18 C19 C20 C21 1.6(5) . . . . ?
N6 C20 C21 C22 -1.2(5) . . . . ?
C19 C20 C21 C22 178.8(3) . . . . ?
N6 C20 C21 C26 179.4(3) . . . . ?
C19 C20 C21 C26 -0.6(5) . . . . ?
C20 C21 C22 C23 0.5(5) . . . . ?
C26 C21 C22 C23 179.8(4) . . . . ?
C21 C22 C23 C24 0.6(6) . . . . ?
C20 N6 C24 C23 0.3(5) . . . . ?
Zn1 N6 C24 C23 -177.7(3) . . . . ?
C22 C23 C24 N6 -1.0(6) . . . . ?
C19 C18 C25 C26 0.1(6) . . . . ?
C17 C18 C25 C26 179.3(4) . . . . ?
C18 C25 C26 C21 0.9(7) . . . . ?
C20 C21 C26 C25 -0.7(6) . . . . ?
C22 C21 C26 C25 180.0(4) . . . . ?
Zn2 O5 C27 O6 167.5(3) . . . . ?
Zn2 O5 C27 C28 -13.2(3) . . . . ?
C32 N7 C28 C29 -1.6(5) . . . . ?
Zn2 N7 C28 C29 -176.3(3) . . . . ?
C32 N7 C28 C27 178.4(3) . . . . ?
Zn2 N7 C28 C27 3.8(3) . . . . ?
O6 C27 C28 N7 -174.9(3) . . . . ?
O5 C27 C28 N7 5.7(4) . . . . ?
O6 C27 C28 C29 5.1(5) . . . . ?
O5 C27 C28 C29 -174.2(3) . . . . ?
N7 C28 C29 C30 1.6(5) . . . . ?
C27 C28 C29 C30 -178.5(3) . . . . ?
C28 C29 C30 C31 0.0(5) . . . . ?
C29 C30 C31 C32 -1.5(5) . . . . ?
C29 C30 C31 C33 178.2(3) . . . . ?
C28 N7 C32 C31 0.0(4) . . . . ?
Zn2 N7 C32 C31 173.7(2) . . . . ?
C30 C31 C32 N7 1.5(5) . . . . ?
C33 C31 C32 N7 -178.2(3) . . . . ?
Zn2 O7 C34 O8 169.1(3) . . . . ?
Zn2 O7 C34 C35 -10.5(3) . . . . ?
C39 N9 C35 C36 -1.6(4) . . . . ?
Zn2 N9 C35 C36 -175.5(3) . . . . ?
C39 N9 C35 C34 177.7(3) . . . . ?
Zn2 N9 C35 C34 3.8(3) . . . . ?
O8 C34 C35 N9 -175.6(3) . . . . ?
O7 C34 C35 N9 4.0(4) . . . . ?
O8 C34 C35 C36 3.7(5) . . . . ?
O7 C34 C35 C36 -176.7(3) . . . . ?
N9 C35 C36 C37 2.2(5) . . . . ?
C34 C35 C36 C37 -177.1(3) . . . . ?
C35 C36 C37 C38 -0.8(5) . . . . ?
C36 C37 C38 C39 -1.0(5) . . . . ?
C36 C37 C38 C40 177.7(3) . . . . ?
C35 N9 C39 C38 -0.3(4) . . . . ?
Zn2 N9 C39 C38 172.5(2) . . . . ?
C37 C38 C39 N9 1.6(5) . . . . ?
C40 C38 C39 N9 -177.1(3) . . . . ?
C45 N11 C41 C42 -0.7(5) . . . . ?
Zn2 N11 C41 C42 176.6(3) . . . . ?
N11 C41 C42 C43 0.9(6) . . . . ?
C41 C42 C43 C44 0.0(6) . . . . ?
C42 C43 C44 C45 -1.1(5) . . . . ?
C42 C43 C44 C51 179.3(4) . . . . ?
C41 N11 C45 C44 -0.5(5) . . . . ?
Zn2 N11 C45 C44 -178.2(3) . . . . ?
C41 N11 C45 C46 179.8(3) . . . . ?
Zn2 N11 C45 C46 2.1(4) . . . . ?
C43 C44 C45 N11 1.4(5) . . . . ?
C51 C44 C45 N11 -179.0(3) . . . . ?
C43 C44 C45 C46 -178.9(3) . . . . ?
C51 C44 C45 C46 0.7(5) . . . . ?
C50 N12 C46 C47 -0.1(5) . . . . ?
Zn2 N12 C46 C47 -179.3(3) . . . . ?
C50 N12 C46 C45 179.2(3) . . . . ?
Zn2 N12 C46 C45 0.0(4) . . . . ?
N11 C45 C46 N12 -1.4(5) . . . . ?
C44 C45 C46 N12 178.9(3) . . . . ?
N11 C45 C46 C47 177.8(3) . . . . ?
C44 C45 C46 C47 -1.9(5) . . . . ?
N12 C46 C47 C48 0.3(5) . . . . ?
C45 C46 C47 C48 -178.9(3) . . . . ?
N12 C46 C47 C52 -179.4(3) . . . . ?
C45 C46 C47 C52 1.4(5) . . . . ?
C46 C47 C48 C49 -0.3(6) . . . . ?
C52 C47 C48 C49 179.4(4) . . . . ?
C47 C48 C49 C50 0.1(6) . . . . ?
C46 N12 C50 C49 -0.2(5) . . . . ?
Zn2 N12 C50 C49 178.9(3) . . . . ?
C48 C49 C50 N12 0.2(6) . . . . ?
C45 C44 C51 C52 0.9(6) . . . . ?
C43 C44 C51 C52 -179.5(4) . . . . ?
C44 C51 C52 C47 -1.4(7) . . . . ?
C46 C47 C52 C51 0.2(6) . . . . ?
C48 C47 C52 C51 -179.5(4) . . . . ?
C63 C58 C59 C60 0.0 . . . . ?
C57 C58 C59 C60 -177.1(4) . . . . ?
C58 C59 C60 C61 0.0 . . . . ?
C59 C60 C61 C62 0.0 . . . . ?
C60 C61 C62 C63 0.0 . . . . ?
C61 C62 C63 C58 0.0 . . . . ?
C59 C58 C63 C62 0.0 . . . . ?
C57 C58 C63 C62 177.1(4) . . . . ?
C70 C65 C66 C67 0.0 . . . . ?
C64 C65 C66 C67 176.6(4) . . . . ?
C65 C66 C67 C68 0.0 . . . . ?
C66 C67 C68 C69 0.0 . . . . ?
C67 C68 C69 C70 0.0 . . . . ?
C68 C69 C70 C65 0.0 . . . . ?
C66 C65 C70 C69 0.0 . . . . ?
C64 C65 C70 C69 -176.7(4) . . . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
O11B H11B O4 0.84 1.95 2.77(3) 165.5 4_665
O12B H12B O8 0.84 1.95 2.682(10) 144.4 .
O12A H12A O8 0.84 2.02 2.785(13) 151.5 .
O11A H11A O4 0.84 2.02 2.67(2) 134.2 4_665
O9 H9 O2 0.84 1.88 2.721(4) 176.6 1_655
O10 H10A O6 0.84 1.89 2.721(4) 170.3 1_554

_refine_diff_density_max         1.851
_refine_diff_density_min         -0.767
_refine_diff_density_rms         0.079

