# 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_8
_database_code_depnum_ccdc_archive 'CCDC 1427480'
_audit_update_record             
;
2016-02-01 deposited with the CCDC.
2016-02-17 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         '2(C26 H18 N6 O3 S Zn), C H2 Cl2'
_chemical_formula_sum            'C53 H38 Cl2 N12 O6 S2 Zn2'
_chemical_formula_weight         1204.77

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'
S S 0.1246 0.1234 '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'
Cl Cl 0.1484 0.1585 '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                   11.906(4)
_cell_length_b                   15.107(6)
_cell_length_c                   16.009(5)
_cell_angle_alpha                65.288(15)
_cell_angle_beta                 73.741(17)
_cell_angle_gamma                73.112(17)
_cell_volume                     2461.1(15)
_cell_formula_units_Z            2
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    6643
_cell_measurement_theta_min      2.59
_cell_measurement_theta_max      26.24

_exptl_crystal_description       Prism
_exptl_crystal_colour            yellow
_exptl_crystal_size_max          0.11
_exptl_crystal_size_mid          0.09
_exptl_crystal_size_min          0.06
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.626
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1228
_exptl_absorpt_coefficient_mu    1.236
_exptl_absorpt_correction_type   Multi-scan
_exptl_absorpt_correction_T_min  0.5903
_exptl_absorpt_correction_T_max  0.7453
_exptl_absorpt_process_details   
'SADABS-2014/2 - Bruker AXS area detector scaling and absorption correction'

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      296(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            16505
_diffrn_reflns_av_R_equivalents  0.0675
_diffrn_reflns_av_unetI/netI     0.1146
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_k_min       -18
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_theta_min         1.51
_diffrn_reflns_theta_max         26.35
_reflns_number_total             8262
_reflns_number_gt                4845
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'Sir-92 (Altomare et al., 1993)'
_computing_structure_refinement  'SHELXL-2014 (Sheldrick 2014)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'


_refine_special_details          
; 
 Refinement of F² against ALL reflections.  The weighted R-factor wR and 
 goodness of fit S are based on F², conventional R-factors R are based 
 on F, with F set to zero for negative F². The threshold expression of 
 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is 
 not relevant to the choice of reflections for refinement.  R-factors based 
 on F² are statistically about twice as large as those based on F, and R- 
 factors based on ALL data will be even larger. 
 
The crystals of complex 8 were of poor quality and did not diffract well.
The data was measured 3-4 times on different crystals. The present data set
being the best. As a result of this the ratio of unique to expected reflections
 is low i.e. 0.82. 
Structure of complex 8 has been re-refined with
 some of atoms refined isotropically because
 they turn to N.P.D after anisotropic refinement.
 As these atoms are from the benzene ring, azo and azomethine group.
 There cannot be any error in the atom assignment. These atoms
 do not show any disorder either but could not be refined anistropically.
 This may be due to the observed data being less (58 %).
;

_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)+(0.2000P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    none
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         8262
_refine_ls_number_parameters     679
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1826
_refine_ls_R_factor_gt           0.1169
_refine_ls_wR_factor_ref         0.3884
_refine_ls_wR_factor_gt          0.3046
_refine_ls_goodness_of_fit_ref   1.341
_refine_ls_restrained_S_all      1.341
_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
C1 C 0.9448(9) 0.7322(7) 0.6596(8) 0.028(3) Uani 1 1 d . . .
H1 H 0.8955 0.6869 0.6789 0.034 Uiso 1 1 calc R . .
C2 C 1.0623(9) 0.7067(7) 0.6215(9) 0.036(3) Uani 1 1 d . . .
H2 H 1.0923 0.6451 0.6156 0.043 Uiso 1 1 calc R . .
C3 C 1.1358(9) 0.7754(7) 0.5918(9) 0.035(3) Uani 1 1 d . . .
H3 H 1.2156 0.7595 0.5656 0.043 Uiso 1 1 calc R . .
C4 C 1.0911(8) 0.8662(7) 0.6011(8) 0.028(3) Uani 1 1 d . . .
C5 C 1.1611(8) 0.9401(7) 0.5757(8) 0.028(3) Uani 1 1 d . . .
H5 H 1.2413 0.9278 0.5488 0.034 Uiso 1 1 calc R . .
C6 C 1.1155(9) 1.0238(7) 0.5893(9) 0.035(3) Uani 1 1 d . . .
H6 H 1.1635 1.0700 0.5708 0.042 Uiso 1 1 calc R . .
C7 C 0.9918(8) 1.0462(6) 0.6325(8) 0.025(3) Uani 1 1 d . . .
C8 C 0.9182(8) 0.9771(6) 0.6563(7) 0.021(2) Uani 1 1 d . . .
C9 C 0.9704(7) 0.8852(6) 0.6411(7) 0.022(2) Uani 1 1 d . . .
C10 C 0.9381(9) 1.1326(7) 0.6523(8) 0.029(3) Uani 1 1 d . . .
H10 H 0.9819 1.1807 0.6377 0.035 Uiso 1 1 calc R . .
C11 C 0.8222(9) 1.1452(6) 0.6927(8) 0.029(3) Uani 1 1 d . . .
H11 H 0.7857 1.2017 0.7071 0.034 Uiso 1 1 calc R . .
C12 C 0.7558(8) 1.0725(7) 0.7133(8) 0.033(3) Uani 1 1 d . . .
H12 H 0.6755 1.0829 0.7405 0.040 Uiso 1 1 calc R . .
C13 C 0.7150(7) 0.7430(6) 0.9265(8) 0.025(3) Uani 1 1 d . . .
C14 C 0.7497(8) 0.7221(7) 1.0130(8) 0.026(2) Uani 1 1 d . . .
H14 H 0.7770 0.7706 1.0190 0.031 Uiso 1 1 calc R . .
C15 C 0.7442(8) 0.6337(7) 1.0870(8) 0.024(2) Uani 1 1 d . . .
H15 H 0.7694 0.6214 1.1415 0.029 Uiso 1 1 calc R . .
C16 C 0.6994(8) 0.5618(6) 1.0785(8) 0.024(2) Uani 1 1 d . . .
C17 C 0.6598(8) 0.5789(6) 0.9994(7) 0.025(2) Uani 1 1 d . . .
H17 H 0.6257 0.5317 0.9977 0.030 Uiso 1 1 calc R . .
C18 C 0.6702(7) 0.6672(6) 0.9208(8) 0.026(3) Uani 1 1 d . . .
C19 C 0.6288(8) 0.6781(6) 0.8402(7) 0.023(2) Uani 1 1 d . . .
H19 H 0.5915 0.6290 0.8461 0.028 Uiso 1 1 calc R . .
C20 C 0.5798(8) 0.8267(6) 0.6184(7) 0.0157(18) Uiso 1 1 d . . .
C21 C 0.4967(8) 0.7573(7) 0.5363(8) 0.023(2) Uani 1 1 d . . .
C22 C 0.4957(9) 0.6610(7) 0.6032(9) 0.032(3) Uani 1 1 d . . .
H22 H 0.5188 0.6425 0.6601 0.039 Uiso 1 1 calc R . .
C23 C 0.4596(10) 0.5938(7) 0.5829(9) 0.040(3) Uani 1 1 d . . .
H23 H 0.4601 0.5294 0.6264 0.048 Uiso 1 1 calc R . .
C24 C 0.4230(9) 0.6205(7) 0.4992(9) 0.032(3) Uani 1 1 d . . .
H24 H 0.3996 0.5749 0.4861 0.038 Uiso 1 1 calc R . .
C25 C 0.4223(8) 0.7163(6) 0.4362(8) 0.029(3) Uani 1 1 d . . .
H25 H 0.3966 0.7357 0.3802 0.035 Uiso 1 1 calc R . .
C26 C 0.4588(8) 0.7843(7) 0.4545(8) 0.031(3) Uani 1 1 d . . .
H26 H 0.4576 0.8487 0.4108 0.037 Uiso 1 1 calc R . .
C27 C 0.0373(9) 0.1886(7) 0.8658(8) 0.031(3) Uani 1 1 d . . .
H27 H 0.0669 0.2438 0.8550 0.037 Uiso 1 1 calc R . .
C28 C -0.0823(9) 0.1859(8) 0.9101(9) 0.037(3) Uani 1 1 d . . .
H28 H -0.1297 0.2362 0.9310 0.044 Uiso 1 1 calc R . .
C29 C -0.1265(9) 0.1070(8) 0.9212(8) 0.033(3) Uani 1 1 d . . .
H29 H -0.2064 0.1051 0.9476 0.040 Uiso 1 1 calc R . .
C30 C -0.0553(8) 0.0303(7) 0.8940(8) 0.030(3) Uani 1 1 d . . .
C31 C -0.0972(8) -0.0532(6) 0.9020(8) 0.029(3) Uani 1 1 d . . .
H31 H -0.1766 -0.0578 0.9277 0.035 Uiso 1 1 calc R . .
C32 C -0.0235(8) -0.1247(7) 0.8729(8) 0.026(3) Uani 1 1 d . . .
H32 H -0.0528 -0.1775 0.8771 0.031 Uiso 1 1 calc R . .
C33 C 0.0986(8) -0.1207(7) 0.8357(8) 0.024(2) Uani 1 1 d . . .
C34 C 0.1419(8) -0.0383(6) 0.8229(7) 0.0194(19) Uiso 1 1 d . . .
C35 C 0.0640(8) 0.0390(6) 0.8538(7) 0.022(2) Uani 1 1 d . . .
C36 C 0.1807(8) -0.1935(7) 0.8054(8) 0.028(3) Uani 1 1 d . . .
H36 H 0.1569 -0.2494 0.8107 0.034 Uiso 1 1 calc R . .
C37 C 0.2960(9) -0.1820(6) 0.7679(8) 0.030(3) Uani 1 1 d . . .
H37 H 0.3514 -0.2312 0.7495 0.036 Uiso 1 1 calc R . .
C38 C 0.3309(8) -0.0977(6) 0.7573(8) 0.032(3) Uani 1 1 d . . .
H38 H 0.4094 -0.0907 0.7299 0.038 Uiso 1 1 calc R . .
C39 C 0.2243(8) 0.2679(6) 0.5863(7) 0.023(2) Uani 1 1 d . . .
C40 C 0.1767(8) 0.2981(7) 0.5032(8) 0.027(3) Uani 1 1 d . . .
H40 H 0.1682 0.2497 0.4851 0.032 Uiso 1 1 calc R . .
C41 C 0.1438(9) 0.3958(7) 0.4500(8) 0.029(3) Uani 1 1 d . . .
H41 H 0.1102 0.4132 0.3980 0.035 Uiso 1 1 calc R . .
C42 C 0.1600(8) 0.4690(6) 0.4732(7) 0.025(2) Uani 1 1 d . . .
C43 C 0.2107(8) 0.4432(6) 0.5494(7) 0.021(2) Uani 1 1 d . . .
H43 H 0.2237 0.4929 0.5633 0.025 Uiso 1 1 calc R . .
C44 C 0.2432(8) 0.3446(6) 0.6063(7) 0.024(2) Uani 1 1 d . . .
C45 C 0.3062(8) 0.3272(6) 0.6794(8) 0.028(3) Uani 1 1 d . . .
H45 H 0.3244 0.3822 0.6811 0.033 Uiso 1 1 calc R . .
C46 C 0.4492(8) 0.1595(6) 0.8575(8) 0.026(2) Uani 1 1 d . . .
C47 C 0.5651(8) 0.2366(7) 0.9065(8) 0.026(3) Uani 1 1 d . . .
C48 C 0.5872(8) 0.2323(7) 0.9883(8) 0.030(3) Uani 1 1 d . . .
H48 H 0.5701 0.1800 1.0441 0.036 Uiso 1 1 calc R . .
C49 C 0.6351(8) 0.3060(7) 0.9868(9) 0.034(3) Uani 1 1 d . . .
H49 H 0.6494 0.3032 1.0421 0.041 Uiso 1 1 calc R . .
C50 C 0.6624(8) 0.3851(7) 0.9031(8) 0.029(3) Uani 1 1 d . . .
H50 H 0.6943 0.4348 0.9024 0.034 Uiso 1 1 calc R . .
C51 C 0.6405(9) 0.3874(7) 0.8202(9) 0.037(3) Uani 1 1 d . . .
H51 H 0.6589 0.4386 0.7639 0.045 Uiso 1 1 calc R . .
C52 C 0.5919(8) 0.3144(7) 0.8222(9) 0.034(3) Uani 1 1 d . . .
H52 H 0.5769 0.3166 0.7674 0.041 Uiso 1 1 calc R . .
C53 C 0.0358(10) 0.5052(8) 0.1123(9) 0.042(3) Uani 1 1 d . . .
H53A H -0.0416 0.4926 0.1170 0.050 Uiso 1 1 calc R . .
H53B H 0.0949 0.4452 0.1132 0.050 Uiso 1 1 calc R . .
N1 N 0.8984(6) 0.8195(5) 0.6700(6) 0.0160(17) Uani 1 1 d . . .
N2 N 0.8022(7) 0.9921(5) 0.6957(6) 0.025(2) Uani 1 1 d . . .
N3 N 0.6929(7) 0.4684(6) 1.1558(7) 0.032(2) Uani 1 1 d . . .
N4 N 0.6391(7) 0.7513(5) 0.7592(6) 0.022(2) Uani 1 1 d . . .
N5 N 0.5912(7) 0.7465(5) 0.6925(7) 0.027(2) Uani 1 1 d . . .
N6 N 0.5325(7) 0.8328(5) 0.5476(6) 0.026(2) Uani 1 1 d . . .
H6A H 0.5230 0.8903 0.5037 0.031 Uiso 1 1 calc R . .
N7 N 0.1092(7) 0.1176(5) 0.8390(7) 0.029(2) Uani 1 1 d . . .
N8 N 0.2559(6) -0.0258(5) 0.7848(6) 0.0164(17) Uani 1 1 d . . .
N9 N 0.1295(8) 0.5727(6) 0.4150(8) 0.040(3) Uani 1 1 d . . .
N10 N 0.3388(6) 0.2416(5) 0.7422(6) 0.0152(15) Uiso 1 1 d . . .
N11 N 0.4107(7) 0.2435(5) 0.7945(7) 0.032(3) Uani 1 1 d . . .
N12 N 0.5228(7) 0.1558(5) 0.9111(7) 0.032(3) Uani 1 1 d . . .
H12A H 0.5459 0.0986 0.9519 0.038 Uiso 1 1 calc R . .
O1 O 0.7235(6) 0.8287(5) 0.8596(6) 0.037(2) Uani 1 1 d . . .
O2 O 0.7503(7) 0.4443(5) 1.2196(6) 0.049(3) Uani 1 1 d . . .
O3 O 0.6340(7) 0.4139(5) 1.1559(6) 0.043(2) Uani 1 1 d . . .
O4 O 0.2500(6) 0.1750(4) 0.6369(6) 0.031(2) Uani 1 1 d . . .
O5 O 0.0818(7) 0.5943(5) 0.3468(6) 0.037(2) Uani 1 1 d . . .
O6 O 0.1513(7) 0.6351(5) 0.4347(6) 0.044(2) Uani 1 1 d . . .
S1 S 0.6146(2) 0.94048(16) 0.6001(2) 0.0263(7) Uani 1 1 d . . .
S2 S 0.4209(2) 0.04387(17) 0.8759(2) 0.0354(8) Uani 1 1 d . . .
Zn1 Zn 0.72188(9) 0.86995(7) 0.72414(9) 0.0233(4) Uani 1 1 d . . .
Zn2 Zn 0.28622(9) 0.11208(7) 0.76875(9) 0.0233(4) Uani 1 1 d . . .
Cl1 Cl 0.0341(3) 0.5333(2) 0.2078(2) 0.0472(9) Uani 1 1 d . . .
Cl2 Cl 0.0700(3) 0.6047(2) 0.0044(2) 0.0441(8) Uani 1 1 d . . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
C1 N1 1.334(12) . ?
C1 C2 1.373(15) . ?
C1 H1 0.9300 . ?
C2 C3 1.396(14) . ?
C2 H2 0.9300 . ?
C3 C4 1.375(15) . ?
C3 H3 0.9300 . ?
C4 C9 1.399(14) . ?
C4 C5 1.441(12) . ?
C5 C6 1.306(15) . ?
C5 H5 0.9300 . ?
C6 C7 1.449(15) . ?
C6 H6 0.9300 . ?
C7 C10 1.400(15) . ?
C7 C8 1.421(11) . ?
C8 N2 1.343(13) . ?
C8 C9 1.438(13) . ?
C9 N1 1.350(10) . ?
C10 C11 1.345(15) . ?
C10 H10 0.9300 . ?
C11 C12 1.413(12) . ?
C11 H11 0.9300 . ?
C12 N2 1.291(13) . ?
C12 H12 0.9300 . ?
C13 O1 1.300(11) . ?
C13 C18 1.440(12) . ?
C13 C14 1.438(14) . ?
C14 C15 1.370(13) . ?
C14 H14 0.9300 . ?
C15 C16 1.408(12) . ?
C15 H15 0.9300 . ?
C16 C17 1.373(14) . ?
C16 N3 1.442(12) . ?
C17 C18 1.408(13) . ?
C17 H17 0.9300 . ?
C18 C19 1.438(14) . ?
C19 N4 1.307(12) . ?
C19 H19 0.9300 . ?
C20 N5 1.299(11) . ?
C20 N6 1.359(11) . ?
C20 S1 1.771(8) . ?
C21 C26 1.365(14) . ?
C21 C22 1.401(13) . ?
C21 N6 1.419(11) . ?
C22 C23 1.390(13) . ?
C22 H22 0.9300 . ?
C23 C24 1.385(16) . ?
C23 H23 0.9300 . ?
C24 C25 1.374(13) . ?
C24 H24 0.9300 . ?
C25 C26 1.383(13) . ?
C25 H25 0.9300 . ?
C26 H26 0.9300 . ?
C27 N7 1.309(14) . ?
C27 C28 1.405(16) . ?
C27 H27 0.9300 . ?
C28 C29 1.366(14) . ?
C28 H28 0.9300 . ?
C29 C30 1.377(16) . ?
C29 H29 0.9300 . ?
C30 C35 1.405(13) . ?
C30 C31 1.432(13) . ?
C31 C32 1.340(15) . ?
C31 H31 0.9300 . ?
C32 C33 1.418(13) . ?
C32 H32 0.9300 . ?
C33 C34 1.399(12) . ?
C33 C36 1.399(15) . ?
C34 N8 1.355(12) . ?
C34 C35 1.437(14) . ?
C35 N7 1.349(11) . ?
C36 C37 1.366(14) . ?
C36 H36 0.9300 . ?
C37 C38 1.382(12) . ?
C37 H37 0.9300 . ?
C38 N8 1.337(13) . ?
C38 H38 0.9300 . ?
C39 O4 1.287(10) . ?
C39 C44 1.414(13) . ?
C39 C40 1.437(13) . ?
C40 C41 1.363(12) . ?
C40 H40 0.9300 . ?
C41 C42 1.381(13) . ?
C41 H41 0.9300 . ?
C42 C43 1.372(13) . ?
C42 N9 1.446(11) . ?
C43 C44 1.387(11) . ?
C43 H43 0.9300 . ?
C44 C45 1.457(13) . ?
C45 N10 1.293(11) . ?
C45 H45 0.9300 . ?
C46 N11 1.299(11) . ?
C46 N12 1.363(12) . ?
C46 S2 1.762(9) . ?
C47 C48 1.378(15) . ?
C47 C52 1.397(15) . ?
C47 N12 1.419(11) . ?
C48 C49 1.379(13) . ?
C48 H48 0.9300 . ?
C49 C50 1.405(15) . ?
C49 H49 0.9300 . ?
C50 C51 1.407(16) . ?
C50 H50 0.9300 . ?
C51 C52 1.372(12) . ?
C51 H51 0.9300 . ?
C52 H52 0.9300 . ?
C53 Cl1 1.743(13) . ?
C53 Cl2 1.789(12) . ?
C53 H53A 0.9700 . ?
C53 H53B 0.9700 . ?
N1 Zn1 2.085(8) . ?
N2 Zn1 2.147(6) . ?
N3 O3 1.226(10) . ?
N3 O2 1.256(11) . ?
N4 N5 1.378(11) . ?
N4 Zn1 2.092(7) . ?
N6 H6A 0.8600 . ?
N7 Zn2 2.089(9) . ?
N8 Zn2 2.115(7) . ?
N9 O6 1.221(11) . ?
N9 O5 1.251(11) . ?
N10 N11 1.368(10) . ?
N10 Zn2 2.067(7) . ?
N12 H12A 0.8600 . ?
O1 Zn1 1.994(9) . ?
O4 Zn2 2.035(7) . ?
S1 Zn1 2.360(3) . ?
S2 Zn2 2.384(2) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
N1 C1 C2 122.6(9) . . ?
N1 C1 H1 118.7 . . ?
C2 C1 H1 118.7 . . ?
C1 C2 C3 118.5(10) . . ?
C1 C2 H2 120.7 . . ?
C3 C2 H2 120.7 . . ?
C4 C3 C2 120.5(10) . . ?
C4 C3 H3 119.7 . . ?
C2 C3 H3 119.7 . . ?
C3 C4 C9 116.8(9) . . ?
C3 C4 C5 124.4(10) . . ?
C9 C4 C5 118.8(10) . . ?
C6 C5 C4 122.1(10) . . ?
C6 C5 H5 119.0 . . ?
C4 C5 H5 119.0 . . ?
C5 C6 C7 121.4(8) . . ?
C5 C6 H6 119.3 . . ?
C7 C6 H6 119.3 . . ?
C10 C7 C8 116.8(9) . . ?
C10 C7 C6 124.5(8) . . ?
C8 C7 C6 118.6(9) . . ?
N2 C8 C7 122.7(9) . . ?
N2 C8 C9 118.3(7) . . ?
C7 C8 C9 118.9(9) . . ?
N1 C9 C4 123.3(9) . . ?
N1 C9 C8 116.6(8) . . ?
C4 C9 C8 120.1(8) . . ?
C11 C10 C7 119.1(8) . . ?
C11 C10 H10 120.5 . . ?
C7 C10 H10 120.5 . . ?
C10 C11 C12 120.1(10) . . ?
C10 C11 H11 120.0 . . ?
C12 C11 H11 120.0 . . ?
N2 C12 C11 122.5(10) . . ?
N2 C12 H12 118.7 . . ?
C11 C12 H12 118.7 . . ?
O1 C13 C18 124.2(9) . . ?
O1 C13 C14 118.7(8) . . ?
C18 C13 C14 117.0(8) . . ?
C15 C14 C13 122.6(9) . . ?
C15 C14 H14 118.7 . . ?
C13 C14 H14 118.7 . . ?
C14 C15 C16 118.4(9) . . ?
C14 C15 H15 120.8 . . ?
C16 C15 H15 120.8 . . ?
C17 C16 C15 121.8(8) . . ?
C17 C16 N3 119.1(8) . . ?
C15 C16 N3 119.0(9) . . ?
C16 C17 C18 120.7(9) . . ?
C16 C17 H17 119.7 . . ?
C18 C17 H17 119.7 . . ?
C17 C18 C13 119.3(9) . . ?
C17 C18 C19 117.0(8) . . ?
C13 C18 C19 123.6(8) . . ?
N4 C19 C18 125.5(8) . . ?
N4 C19 H19 117.2 . . ?
C18 C19 H19 117.2 . . ?
N5 C20 N6 122.2(8) . . ?
N5 C20 S1 125.1(7) . . ?
N6 C20 S1 112.6(6) . . ?
C26 C21 C22 119.9(9) . . ?
C26 C21 N6 115.6(8) . . ?
C22 C21 N6 124.5(9) . . ?
C23 C22 C21 118.6(10) . . ?
C23 C22 H22 120.7 . . ?
C21 C22 H22 120.7 . . ?
C24 C23 C22 121.5(9) . . ?
C24 C23 H23 119.2 . . ?
C22 C23 H23 119.2 . . ?
C25 C24 C23 118.3(9) . . ?
C25 C24 H24 120.9 . . ?
C23 C24 H24 120.9 . . ?
C24 C25 C26 121.3(10) . . ?
C24 C25 H25 119.4 . . ?
C26 C25 H25 119.4 . . ?
C21 C26 C25 120.3(9) . . ?
C21 C26 H26 119.8 . . ?
C25 C26 H26 119.8 . . ?
N7 C27 C28 123.5(9) . . ?
N7 C27 H27 118.2 . . ?
C28 C27 H27 118.2 . . ?
C29 C28 C27 117.7(11) . . ?
C29 C28 H28 121.2 . . ?
C27 C28 H28 121.2 . . ?
C28 C29 C30 121.4(10) . . ?
C28 C29 H29 119.3 . . ?
C30 C29 H29 119.3 . . ?
C29 C30 C35 116.0(9) . . ?
C29 C30 C31 123.9(9) . . ?
C35 C30 C31 120.1(10) . . ?
C32 C31 C30 120.9(9) . . ?
C32 C31 H31 119.5 . . ?
C30 C31 H31 119.5 . . ?
C31 C32 C33 120.6(9) . . ?
C31 C32 H32 119.7 . . ?
C33 C32 H32 119.7 . . ?
C34 C33 C36 116.2(9) . . ?
C34 C33 C32 120.2(10) . . ?
C36 C33 C32 123.5(9) . . ?
N8 C34 C33 124.6(9) . . ?
N8 C34 C35 115.7(8) . . ?
C33 C34 C35 119.6(9) . . ?
N7 C35 C30 124.0(10) . . ?
N7 C35 C34 117.6(8) . . ?
C30 C35 C34 118.4(9) . . ?
C37 C36 C33 119.5(9) . . ?
C37 C36 H36 120.3 . . ?
C33 C36 H36 120.3 . . ?
C36 C37 C38 120.5(10) . . ?
C36 C37 H37 119.8 . . ?
C38 C37 H37 119.8 . . ?
N8 C38 C37 122.3(9) . . ?
N8 C38 H38 118.8 . . ?
C37 C38 H38 118.8 . . ?
O4 C39 C44 123.5(8) . . ?
O4 C39 C40 120.1(8) . . ?
C44 C39 C40 116.4(8) . . ?
C41 C40 C39 121.8(9) . . ?
C41 C40 H40 119.1 . . ?
C39 C40 H40 119.1 . . ?
C40 C41 C42 120.2(9) . . ?
C40 C41 H41 119.9 . . ?
C42 C41 H41 119.9 . . ?
C43 C42 C41 119.8(8) . . ?
C43 C42 N9 119.7(9) . . ?
C41 C42 N9 120.4(9) . . ?
C42 C43 C44 121.6(9) . . ?
C42 C43 H43 119.2 . . ?
C44 C43 H43 119.2 . . ?
C43 C44 C39 120.0(8) . . ?
C43 C44 C45 115.9(8) . . ?
C39 C44 C45 123.8(8) . . ?
N10 C45 C44 125.4(8) . . ?
N10 C45 H45 117.3 . . ?
C44 C45 H45 117.3 . . ?
N11 C46 N12 120.0(8) . . ?
N11 C46 S2 124.6(8) . . ?
N12 C46 S2 115.2(6) . . ?
C48 C47 C52 120.5(9) . . ?
C48 C47 N12 117.1(9) . . ?
C52 C47 N12 122.3(10) . . ?
C49 C48 C47 119.5(10) . . ?
C49 C48 H48 120.2 . . ?
C47 C48 H48 120.2 . . ?
C48 C49 C50 121.0(10) . . ?
C48 C49 H49 119.5 . . ?
C50 C49 H49 119.5 . . ?
C49 C50 C51 118.4(9) . . ?
C49 C50 H50 120.8 . . ?
C51 C50 H50 120.8 . . ?
C52 C51 C50 120.3(10) . . ?
C52 C51 H51 119.9 . . ?
C50 C51 H51 119.9 . . ?
C51 C52 C47 120.2(11) . . ?
C51 C52 H52 119.9 . . ?
C47 C52 H52 119.9 . . ?
Cl1 C53 Cl2 111.2(6) . . ?
Cl1 C53 H53A 109.4 . . ?
Cl2 C53 H53A 109.4 . . ?
Cl1 C53 H53B 109.4 . . ?
Cl2 C53 H53B 109.4 . . ?
H53A C53 H53B 108.0 . . ?
C1 N1 C9 118.2(8) . . ?
C1 N1 Zn1 127.2(6) . . ?
C9 N1 Zn1 114.6(6) . . ?
C12 N2 C8 118.8(7) . . ?
C12 N2 Zn1 129.3(7) . . ?
C8 N2 Zn1 111.9(6) . . ?
O3 N3 O2 122.2(8) . . ?
O3 N3 C16 118.9(8) . . ?
O2 N3 C16 118.9(8) . . ?
C19 N4 N5 115.2(7) . . ?
C19 N4 Zn1 125.8(6) . . ?
N5 N4 Zn1 119.0(6) . . ?
C20 N5 N4 116.0(7) . . ?
C20 N6 C21 129.0(8) . . ?
C20 N6 H6A 115.5 . . ?
C21 N6 H6A 115.5 . . ?
C27 N7 C35 117.4(9) . . ?
C27 N7 Zn2 128.3(6) . . ?
C35 N7 Zn2 114.2(7) . . ?
C38 N8 C34 116.9(7) . . ?
C38 N8 Zn2 128.9(6) . . ?
C34 N8 Zn2 114.1(6) . . ?
O6 N9 O5 123.0(8) . . ?
O6 N9 C42 118.6(8) . . ?
O5 N9 C42 118.4(8) . . ?
C45 N10 N11 113.7(7) . . ?
C45 N10 Zn2 125.3(6) . . ?
N11 N10 Zn2 120.9(5) . . ?
C46 N11 N10 117.0(8) . . ?
C46 N12 C47 126.7(7) . . ?
C46 N12 H12A 116.7 . . ?
C47 N12 H12A 116.7 . . ?
C13 O1 Zn1 128.9(7) . . ?
C39 O4 Zn2 128.6(7) . . ?
C20 S1 Zn1 94.3(3) . . ?
C46 S2 Zn2 94.9(3) . . ?
O1 Zn1 N1 103.1(3) . . ?
O1 Zn1 N4 88.4(3) . . ?
N1 Zn1 N4 103.6(3) . . ?
O1 Zn1 N2 88.8(3) . . ?
N1 Zn1 N2 78.5(3) . . ?
N4 Zn1 N2 176.8(4) . . ?
O1 Zn1 S1 149.6(2) . . ?
N1 Zn1 S1 107.2(2) . . ?
N4 Zn1 S1 82.1(2) . . ?
N2 Zn1 S1 99.6(2) . . ?
O4 Zn2 N10 87.2(3) . . ?
O4 Zn2 N7 96.7(3) . . ?
N10 Zn2 N7 109.8(3) . . ?
O4 Zn2 N8 91.1(3) . . ?
N10 Zn2 N8 172.0(3) . . ?
N7 Zn2 N8 78.1(3) . . ?
O4 Zn2 S2 152.1(2) . . ?
N10 Zn2 S2 82.07(19) . . ?
N7 Zn2 S2 111.2(3) . . ?
N8 Zn2 S2 95.9(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
N1 C1 C2 C3 -0.6(17) . . . . ?
C1 C2 C3 C4 0.3(17) . . . . ?
C2 C3 C4 C9 -0.1(16) . . . . ?
C2 C3 C4 C5 177.6(10) . . . . ?
C3 C4 C5 C6 -177.3(11) . . . . ?
C9 C4 C5 C6 0.4(16) . . . . ?
C4 C5 C6 C7 1.2(17) . . . . ?
C5 C6 C7 C10 177.6(10) . . . . ?
C5 C6 C7 C8 -2.9(16) . . . . ?
C10 C7 C8 N2 0.2(14) . . . . ?
C6 C7 C8 N2 -179.3(9) . . . . ?
C10 C7 C8 C9 -177.4(9) . . . . ?
C6 C7 C8 C9 3.1(14) . . . . ?
C3 C4 C9 N1 0.1(15) . . . . ?
C5 C4 C9 N1 -177.8(9) . . . . ?
C3 C4 C9 C8 177.7(9) . . . . ?
C5 C4 C9 C8 -0.1(15) . . . . ?
N2 C8 C9 N1 -1.6(13) . . . . ?
C7 C8 C9 N1 176.1(8) . . . . ?
N2 C8 C9 C4 -179.4(9) . . . . ?
C7 C8 C9 C4 -1.7(14) . . . . ?
C8 C7 C10 C11 0.5(14) . . . . ?
C6 C7 C10 C11 -180.0(10) . . . . ?
C7 C10 C11 C12 -1.0(15) . . . . ?
C10 C11 C12 N2 0.7(16) . . . . ?
O1 C13 C14 C15 -179.7(10) . . . . ?
C18 C13 C14 C15 1.7(14) . . . . ?
C13 C14 C15 C16 -1.9(15) . . . . ?
C14 C15 C16 C17 -1.1(15) . . . . ?
C14 C15 C16 N3 -180.0(9) . . . . ?
C15 C16 C17 C18 4.3(15) . . . . ?
N3 C16 C17 C18 -176.8(9) . . . . ?
C16 C17 C18 C13 -4.5(15) . . . . ?
C16 C17 C18 C19 178.7(9) . . . . ?
O1 C13 C18 C17 -177.0(9) . . . . ?
C14 C13 C18 C17 1.5(13) . . . . ?
O1 C13 C18 C19 -0.4(16) . . . . ?
C14 C13 C18 C19 178.1(9) . . . . ?
C17 C18 C19 N4 -174.8(10) . . . . ?
C13 C18 C19 N4 8.5(16) . . . . ?
C26 C21 C22 C23 2.2(17) . . . . ?
N6 C21 C22 C23 -179.4(10) . . . . ?
C21 C22 C23 C24 -1.1(18) . . . . ?
C22 C23 C24 C25 -0.5(18) . . . . ?
C23 C24 C25 C26 1.1(17) . . . . ?
C22 C21 C26 C25 -1.6(16) . . . . ?
N6 C21 C26 C25 179.8(9) . . . . ?
C24 C25 C26 C21 -0.1(16) . . . . ?
N7 C27 C28 C29 -3.3(17) . . . . ?
C27 C28 C29 C30 3.0(16) . . . . ?
C28 C29 C30 C35 -0.7(16) . . . . ?
C28 C29 C30 C31 -178.6(10) . . . . ?
C29 C30 C31 C32 179.0(11) . . . . ?
C35 C30 C31 C32 1.1(15) . . . . ?
C30 C31 C32 C33 1.7(16) . . . . ?
C31 C32 C33 C34 -4.5(15) . . . . ?
C31 C32 C33 C36 179.0(10) . . . . ?
C36 C33 C34 N8 -0.8(14) . . . . ?
C32 C33 C34 N8 -177.5(9) . . . . ?
C36 C33 C34 C35 -178.8(9) . . . . ?
C32 C33 C34 C35 4.4(14) . . . . ?
C29 C30 C35 N7 -1.7(15) . . . . ?
C31 C30 C35 N7 176.3(9) . . . . ?
C29 C30 C35 C34 -179.1(9) . . . . ?
C31 C30 C35 C34 -1.1(14) . . . . ?
N8 C34 C35 N7 2.5(13) . . . . ?
C33 C34 C35 N7 -179.3(8) . . . . ?
N8 C34 C35 C30 -179.9(9) . . . . ?
C33 C34 C35 C30 -1.6(14) . . . . ?
C34 C33 C36 C37 1.4(14) . . . . ?
C32 C33 C36 C37 178.1(10) . . . . ?
C33 C36 C37 C38 -2.0(15) . . . . ?
C36 C37 C38 N8 1.8(16) . . . . ?
O4 C39 C40 C41 177.2(10) . . . . ?
C44 C39 C40 C41 -4.5(15) . . . . ?
C39 C40 C41 C42 2.6(17) . . . . ?
C40 C41 C42 C43 0.7(16) . . . . ?
C40 C41 C42 N9 177.6(10) . . . . ?
C41 C42 C43 C44 -2.1(16) . . . . ?
N9 C42 C43 C44 -179.0(9) . . . . ?
C42 C43 C44 C39 0.0(16) . . . . ?
C42 C43 C44 C45 174.5(10) . . . . ?
O4 C39 C44 C43 -178.6(10) . . . . ?
C40 C39 C44 C43 3.1(14) . . . . ?
O4 C39 C44 C45 7.4(16) . . . . ?
C40 C39 C44 C45 -170.9(10) . . . . ?
C43 C44 C45 N10 176.5(10) . . . . ?
C39 C44 C45 N10 -9.3(17) . . . . ?
C52 C47 C48 C49 0.7(15) . . . . ?
N12 C47 C48 C49 176.2(8) . . . . ?
C47 C48 C49 C50 -0.5(15) . . . . ?
C48 C49 C50 C51 -0.3(15) . . . . ?
C49 C50 C51 C52 0.9(15) . . . . ?
C50 C51 C52 C47 -0.7(16) . . . . ?
C48 C47 C52 C51 -0.1(15) . . . . ?
N12 C47 C52 C51 -175.5(9) . . . . ?
C2 C1 N1 C9 0.5(15) . . . . ?
C2 C1 N1 Zn1 178.8(8) . . . . ?
C4 C9 N1 C1 -0.3(14) . . . . ?
C8 C9 N1 C1 -178.0(8) . . . . ?
C4 C9 N1 Zn1 -178.8(8) . . . . ?
C8 C9 N1 Zn1 3.5(11) . . . . ?
C11 C12 N2 C8 0.0(15) . . . . ?
C11 C12 N2 Zn1 177.9(7) . . . . ?
C7 C8 N2 C12 -0.5(14) . . . . ?
C9 C8 N2 C12 177.1(9) . . . . ?
C7 C8 N2 Zn1 -178.7(7) . . . . ?
C9 C8 N2 Zn1 -1.1(11) . . . . ?
C17 C16 N3 O3 -12.6(15) . . . . ?
C15 C16 N3 O3 166.3(9) . . . . ?
C17 C16 N3 O2 165.7(10) . . . . ?
C15 C16 N3 O2 -15.5(15) . . . . ?
C18 C19 N4 N5 -179.2(9) . . . . ?
C18 C19 N4 Zn1 1.6(15) . . . . ?
N6 C20 N5 N4 -179.2(9) . . . . ?
S1 C20 N5 N4 -2.8(13) . . . . ?
C19 N4 N5 C20 167.3(9) . . . . ?
Zn1 N4 N5 C20 -13.5(11) . . . . ?
N5 C20 N6 C21 -5.0(16) . . . . ?
S1 C20 N6 C21 178.2(8) . . . . ?
C26 C21 N6 C20 -176.1(10) . . . . ?
C22 C21 N6 C20 5.4(17) . . . . ?
C28 C27 N7 C35 1.1(16) . . . . ?
C28 C27 N7 Zn2 177.7(8) . . . . ?
C30 C35 N7 C27 1.4(15) . . . . ?
C34 C35 N7 C27 178.9(9) . . . . ?
C30 C35 N7 Zn2 -175.6(8) . . . . ?
C34 C35 N7 Zn2 1.8(11) . . . . ?
C37 C38 N8 C34 -1.1(14) . . . . ?
C37 C38 N8 Zn2 -176.1(7) . . . . ?
C33 C34 N8 C38 0.6(14) . . . . ?
C35 C34 N8 C38 178.7(9) . . . . ?
C33 C34 N8 Zn2 176.4(7) . . . . ?
C35 C34 N8 Zn2 -5.5(10) . . . . ?
C43 C42 N9 O6 1.0(16) . . . . ?
C41 C42 N9 O6 -175.9(10) . . . . ?
C43 C42 N9 O5 -179.0(10) . . . . ?
C41 C42 N9 O5 4.1(16) . . . . ?
C44 C45 N10 N11 171.5(10) . . . . ?
C44 C45 N10 Zn2 -10.8(16) . . . . ?
N12 C46 N11 N10 178.9(9) . . . . ?
S2 C46 N11 N10 3.1(16) . . . . ?
C45 N10 N11 C46 -178.4(10) . . . . ?
Zn2 N10 N11 C46 3.8(13) . . . . ?
N11 C46 N12 C47 0.0(18) . . . . ?
S2 C46 N12 C47 176.2(9) . . . . ?
C48 C47 N12 C46 149.5(11) . . . . ?
C52 C47 N12 C46 -35.0(16) . . . . ?
C18 C13 O1 Zn1 -17.8(14) . . . . ?
C14 C13 O1 Zn1 163.7(7) . . . . ?
C44 C39 O4 Zn2 15.2(14) . . . . ?
C40 C39 O4 Zn2 -166.7(7) . . . . ?
N5 C20 S1 Zn1 14.0(9) . . . . ?
N6 C20 S1 Zn1 -169.4(7) . . . . ?
N11 C46 S2 Zn2 -6.7(11) . . . . ?
N12 C46 S2 Zn2 177.3(8) . . . . ?
C13 O1 Zn1 N1 -83.1(8) . . . . ?
C13 O1 Zn1 N4 20.5(8) . . . . ?
C13 O1 Zn1 N2 -161.1(8) . . . . ?
C13 O1 Zn1 S1 91.8(9) . . . . ?
C1 N1 Zn1 O1 92.5(8) . . . . ?
C9 N1 Zn1 O1 -89.2(7) . . . . ?
C1 N1 Zn1 N4 1.0(8) . . . . ?
C9 N1 Zn1 N4 179.3(6) . . . . ?
C1 N1 Zn1 N2 178.6(8) . . . . ?
C9 N1 Zn1 N2 -3.1(6) . . . . ?
C1 N1 Zn1 S1 -84.8(8) . . . . ?
C9 N1 Zn1 S1 93.5(6) . . . . ?
C19 N4 Zn1 O1 -12.3(9) . . . . ?
N5 N4 Zn1 O1 168.6(7) . . . . ?
C19 N4 Zn1 N1 90.8(9) . . . . ?
N5 N4 Zn1 N1 -88.4(7) . . . . ?
C19 N4 Zn1 S1 -163.4(9) . . . . ?
N5 N4 Zn1 S1 17.5(6) . . . . ?
C12 N2 Zn1 O1 -72.2(9) . . . . ?
C8 N2 Zn1 O1 105.8(7) . . . . ?
C12 N2 Zn1 N1 -175.8(9) . . . . ?
C8 N2 Zn1 N1 2.2(6) . . . . ?
C12 N2 Zn1 S1 78.5(9) . . . . ?
C8 N2 Zn1 S1 -103.5(6) . . . . ?
C20 S1 Zn1 O1 -86.6(5) . . . . ?
C20 S1 Zn1 N1 88.2(4) . . . . ?
C20 S1 Zn1 N4 -13.7(4) . . . . ?
C20 S1 Zn1 N2 169.1(4) . . . . ?
C39 O4 Zn2 N10 -25.0(8) . . . . ?
C39 O4 Zn2 N7 84.7(8) . . . . ?
C39 O4 Zn2 N8 162.9(8) . . . . ?
C39 O4 Zn2 S2 -92.3(9) . . . . ?
C45 N10 Zn2 O4 22.1(9) . . . . ?
N11 N10 Zn2 O4 -160.4(8) . . . . ?
C45 N10 Zn2 N7 -74.0(10) . . . . ?
N11 N10 Zn2 N7 103.5(8) . . . . ?
C45 N10 Zn2 S2 176.2(9) . . . . ?
N11 N10 Zn2 S2 -6.2(7) . . . . ?
C27 N7 Zn2 O4 -90.5(9) . . . . ?
C35 N7 Zn2 O4 86.2(7) . . . . ?
C27 N7 Zn2 N10 -1.0(10) . . . . ?
C35 N7 Zn2 N10 175.6(6) . . . . ?
C27 N7 Zn2 N8 179.8(9) . . . . ?
C35 N7 Zn2 N8 -3.6(6) . . . . ?
C27 N7 Zn2 S2 88.0(9) . . . . ?
C35 N7 Zn2 S2 -95.4(7) . . . . ?
C38 N8 Zn2 O4 83.5(9) . . . . ?
C34 N8 Zn2 O4 -91.6(7) . . . . ?
C38 N8 Zn2 N7 -179.9(9) . . . . ?
C34 N8 Zn2 N7 4.9(6) . . . . ?
C38 N8 Zn2 S2 -69.4(8) . . . . ?
C34 N8 Zn2 S2 115.4(6) . . . . ?
C46 S2 Zn2 O4 74.1(6) . . . . ?
C46 S2 Zn2 N10 5.6(4) . . . . ?
C46 S2 Zn2 N7 -102.7(4) . . . . ?
C46 S2 Zn2 N8 177.8(4) . . . . ?

_diffrn_measured_fraction_theta_max 0.824
_diffrn_reflns_theta_full        26.35
_diffrn_measured_fraction_theta_full 0.824
_refine_diff_density_max         2.117
_refine_diff_density_min         -3.079
_refine_diff_density_rms         0.297
# start Validation Reply Form
_vrf_PLAT022_shelxl              
;
RESPONSE: This Alert is due to the low ratio 
of unique to expected reflections i.e. 0.82.
;
_vrf_PLAT029_shelxl              
;
RESPONSE: This Alert is due to the low ratio 
of unique to expected reflections i.e. 0.82. 
;
_vrf_PLAT973_shelxl              
;
RESPONSE: This Alert is due to the presence of 
large electron density. 
;
# end Validation Reply Form 

####################################################################### 
# 
# 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_1
_database_code_depnum_ccdc_archive 'CCDC 1427481'
_audit_update_record             
;
2016-02-01 deposited with the CCDC.
2016-02-17 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         '4(C18 H14 N6 O3 S Zn), C O'
_chemical_formula_sum            'C73 H60 N24 O13 S4 Zn4'
_chemical_formula_weight         1871.17

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'
S S 0.1246 0.1234 '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                   10.550(3)
_cell_length_b                   12.969(4)
_cell_length_c                   14.219(4)
_cell_angle_alpha                103.147(14)
_cell_angle_beta                 92.137(16)
_cell_angle_gamma                98.310(15)
_cell_volume                     1869.5(9)
_cell_formula_units_Z            1
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    8231
_cell_measurement_theta_min      2.34
_cell_measurement_theta_max      26.33

_exptl_crystal_description       Bolock
_exptl_crystal_colour            colorless
_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.1
_exptl_crystal_size_min          0.1
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.662
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             954
_exptl_absorpt_coefficient_mu    1.462
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.5902
_exptl_absorpt_correction_T_max  0.7454
_exptl_absorpt_process_details   
'SADABS-2014/2 - Bruker AXS area detector scaling and absorption correction'

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      296(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            25644
_diffrn_reflns_av_R_equivalents  0.0667
_diffrn_reflns_av_unetI/netI     0.0619
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_theta_min         1.47
_diffrn_reflns_theta_max         26.42
_reflns_number_total             7552
_reflns_number_gt                6538
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'Sir-92 (Altomare et al., 1993)'
_computing_structure_refinement  'SHELXL-2014 (Sheldrick 2014)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'

_refine_special_details          
; 
 Refinement of F² against ALL reflections.  The weighted R-factor wR and 
 goodness of fit S are based on F², conventional R-factors R are based 
 on F, with F set to zero for negative F². The threshold expression of 
 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is 
 not relevant to the choice of reflections for refinement.  R-factors based 
 on F² are statistically about twice as large as those based on F, and R- 
 factors based on ALL data will be even larger.
There is presence of highly disorderd lattice methanol molecule.
Carbon atom of this solvent is present at inversion centre with
 half occupancy while 
the oxygen atom is disordered over two positions 
about it with 0.5 site occupancy. 
The protons of methyl group of highly disordered lattice 
methanol molecule could not 
be fixed geometrically or located from difference Fourier. 
;

_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)+(0.0822P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         7552
_refine_ls_number_parameters     550
_refine_ls_number_restraints     5
_refine_ls_R_factor_all          0.0478
_refine_ls_R_factor_gt           0.0422
_refine_ls_wR_factor_ref         0.1253
_refine_ls_wR_factor_gt          0.1205
_refine_ls_goodness_of_fit_ref   1.018
_refine_ls_restrained_S_all      1.055
_refine_ls_shift/su_max          0.003
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C 0.1282(3) 0.9884(2) 0.21694(19) 0.0212(6) Uani 1 1 d . . .
H1 H 0.0787 1.0371 0.2493 0.025 Uiso 1 1 calc R . .
C2 C 0.0758(3) 0.8812(2) 0.19033(19) 0.0254(6) Uani 1 1 d . . .
H2 H -0.0080 0.8581 0.2032 0.030 Uiso 1 1 calc R . .
C3 C 0.1511(3) 0.8092(2) 0.1439(2) 0.0282(7) Uani 1 1 d . . .
H3 H 0.1182 0.7365 0.1250 0.034 Uiso 1 1 calc R . .
C4 C 0.2757(3) 0.8456(2) 0.12576(19) 0.0244(6) Uani 1 1 d . . .
H4 H 0.3276 0.7978 0.0953 0.029 Uiso 1 1 calc R . .
C5 C 0.3221(3) 0.9549(2) 0.15376(17) 0.0179(5) Uani 1 1 d . . .
C6 C 0.4544(3) 1.0020(2) 0.13602(17) 0.0190(5) Uani 1 1 d . . .
C7 C 0.5428(3) 0.9394(2) 0.09211(19) 0.0248(6) Uani 1 1 d . . .
H7 H 0.5218 0.8651 0.0743 0.030 Uiso 1 1 calc R . .
C8 C 0.6614(3) 0.9889(2) 0.0755(2) 0.0291(7) Uani 1 1 d . . .
H8 H 0.7219 0.9484 0.0471 0.035 Uiso 1 1 calc R . .
C9 C 0.6898(3) 1.1003(2) 0.10158(19) 0.0267(6) Uani 1 1 d . . .
H9 H 0.7693 1.1353 0.0907 0.032 Uiso 1 1 calc R . .
C10 C 0.5981(3) 1.1578(2) 0.14396(19) 0.0244(6) Uani 1 1 d . . .
H10 H 0.6168 1.2323 0.1606 0.029 Uiso 1 1 calc R . .
C11 C 0.2705(2) 1.2957(2) 0.07696(18) 0.0178(5) Uani 1 1 d . . .
C12 C 0.2216(3) 1.2866(2) -0.01978(19) 0.0255(6) Uani 1 1 d . . .
H12 H 0.1749 1.2216 -0.0539 0.031 Uiso 1 1 calc R . .
C13 C 0.2408(3) 1.3703(2) -0.06467(19) 0.0261(6) Uani 1 1 d . . .
H13 H 0.2096 1.3613 -0.1285 0.031 Uiso 1 1 calc R . .
C14 C 0.3073(3) 1.4684(2) -0.01361(18) 0.0214(6) Uani 1 1 d . . .
C15 C 0.3518(3) 1.4828(2) 0.08215(18) 0.0198(6) Uani 1 1 d . . .
H15 H 0.3927 1.5501 0.1161 0.024 Uiso 1 1 calc R . .
C16 C 0.3364(2) 1.3982(2) 0.12891(17) 0.0165(5) Uani 1 1 d . . .
C17 C 0.3823(2) 1.42340(19) 0.22946(18) 0.0158(5) Uani 1 1 d . . .
H17 H 0.4103 1.4952 0.2592 0.019 Uiso 1 1 calc R . .
C18 C 0.4198(2) 1.33003(19) 0.43421(17) 0.0156(5) Uani 1 1 d . . .
C19 C 0.7504(3) 0.3253(2) 0.4569(2) 0.0293(7) Uani 1 1 d . . .
H19 H 0.7257 0.2524 0.4520 0.035 Uiso 1 1 calc R . .
C20 C 0.7284(3) 0.3667(3) 0.3770(2) 0.0337(7) Uani 1 1 d . . .
H20 H 0.6911 0.3219 0.3190 0.040 Uiso 1 1 calc R . .
C21 C 0.7625(3) 0.4743(3) 0.3846(2) 0.0347(7) Uani 1 1 d . . .
H21 H 0.7485 0.5038 0.3320 0.042 Uiso 1 1 calc R . .
C22 C 0.8174(3) 0.5378(2) 0.4710(2) 0.0281(6) Uani 1 1 d . . .
H22 H 0.8407 0.6112 0.4778 0.034 Uiso 1 1 calc R . .
C23 C 0.8382(2) 0.4923(2) 0.54827(19) 0.0198(6) Uani 1 1 d . . .
C24 C 0.8976(2) 0.5556(2) 0.6441(2) 0.0202(6) Uani 1 1 d . . .
C25 C 0.9481(3) 0.6642(2) 0.6617(2) 0.0299(7) Uani 1 1 d . . .
H25 H 0.9435 0.7011 0.6130 0.036 Uiso 1 1 calc R . .
C26 C 1.0051(3) 0.7162(2) 0.7525(2) 0.0357(8) Uani 1 1 d . . .
H26 H 1.0390 0.7887 0.7657 0.043 Uiso 1 1 calc R . .
C27 C 1.0112(3) 0.6594(2) 0.8234(2) 0.0338(7) Uani 1 1 d . . .
H27 H 1.0500 0.6926 0.8848 0.041 Uiso 1 1 calc R . .
C28 C 0.9582(3) 0.5520(2) 0.8008(2) 0.0272(6) Uani 1 1 d . . .
H28 H 0.9617 0.5138 0.8486 0.033 Uiso 1 1 calc R . .
C29 C 0.5752(2) 0.24374(19) 0.70253(18) 0.0167(5) Uani 1 1 d . . .
C30 C 0.4555(2) 0.2648(2) 0.73968(18) 0.0196(5) Uani 1 1 d . . .
H30 H 0.4476 0.3351 0.7693 0.023 Uiso 1 1 calc R . .
C31 C 0.3513(2) 0.1860(2) 0.73372(18) 0.0206(6) Uani 1 1 d . . .
H31 H 0.2753 0.2025 0.7602 0.025 Uiso 1 1 calc R . .
C32 C 0.3615(2) 0.0811(2) 0.68723(18) 0.0189(5) Uani 1 1 d . . .
C33 C 0.4733(2) 0.0563(2) 0.64435(18) 0.0188(5) Uani 1 1 d . . .
H33 H 0.4767 -0.0139 0.6117 0.023 Uiso 1 1 calc R . .
C34 C 0.5804(2) 0.1352(2) 0.64961(18) 0.0161(5) Uani 1 1 d . . .
C35 C 0.6941(2) 0.09887(19) 0.60636(17) 0.0160(5) Uani 1 1 d . . .
H35 H 0.6877 0.0269 0.5750 0.019 Uiso 1 1 calc R . .
C36 C 1.0171(3) 0.1666(2) 0.58895(19) 0.0203(6) Uani 1 1 d . . .
C37 C 1.0000 1.0000 0.0000 0.0668(19) Uani 1 2 d SD . .
N1 N 0.2477(2) 1.02523(17) 0.19813(15) 0.0186(5) Uani 1 1 d . . .
N2 N 0.4822(2) 1.10988(16) 0.16219(15) 0.0176(4) Uani 1 1 d . . .
N3 N 0.3307(2) 1.55792(19) -0.05988(16) 0.0275(6) Uani 1 1 d . . .
N4 N 0.3880(2) 1.35418(17) 0.28197(15) 0.0145(4) Uani 1 1 d . . .
N5 N 0.4290(2) 1.39867(16) 0.37827(15) 0.0179(5) Uani 1 1 d . . .
N6 N 0.4619(2) 1.36831(19) 0.52784(16) 0.0228(5) Uani 1 1 d D . .
H6A H 0.490(3) 1.4309(16) 0.552(2) 0.027 Uiso 1 1 d D . .
H6B H 0.447(3) 1.324(2) 0.5606(19) 0.027 Uiso 1 1 d D . .
N7 N 0.8057(2) 0.38689(17) 0.54042(15) 0.0192(5) Uani 1 1 d . . .
N8 N 0.9022(2) 0.50049(18) 0.71381(16) 0.0200(5) Uani 1 1 d . . .
N9 N 0.2578(2) -0.00325(19) 0.69081(17) 0.0252(5) Uani 1 1 d . . .
N10 N 0.8036(2) 0.16004(17) 0.60855(15) 0.0173(5) Uani 1 1 d . . .
N11 N 0.9017(2) 0.10815(17) 0.56720(15) 0.0202(5) Uani 1 1 d . . .
N12 N 1.1163(2) 0.1236(2) 0.54839(19) 0.0305(6) Uani 1 1 d D . .
H12A H 1.108(3) 0.0589(17) 0.511(2) 0.037 Uiso 1 1 d D . .
H12B H 1.190(2) 0.159(2) 0.550(2) 0.037 Uiso 1 1 d D . .
O1 O 0.3846(2) 1.64557(16) -0.01149(15) 0.0376(6) Uani 1 1 d . . .
O2 O 0.2986(3) 1.54264(19) -0.14655(15) 0.0495(7) Uani 1 1 d . . .
O3 O 0.24929(18) 1.21219(14) 0.11398(12) 0.0217(4) Uani 1 1 d . . .
O4 O 0.2684(2) -0.09629(17) 0.65248(18) 0.0426(6) Uani 1 1 d . . .
O5 O 0.1637(2) 0.01966(17) 0.73563(17) 0.0367(5) Uani 1 1 d . . .
O6 O 0.67190(17) 0.32076(14) 0.71780(13) 0.0207(4) Uani 1 1 d . . .
O7 O 1.0010(4) 1.0973(3) 0.0536(3) 0.0328(9) Uani 0.50 1 d PD . .
S1 S 0.35733(7) 1.19448(5) 0.39988(5) 0.02381(17) Uani 1 1 d . . .
S2 S 1.05394(6) 0.29299(5) 0.66870(5) 0.02223(17) Uani 1 1 d . . .
Zn1 Zn 0.33853(3) 1.18801(2) 0.23332(2) 0.01598(11) Uani 1 1 d . . .
Zn2 Zn 0.84109(3) 0.32798(2) 0.65988(2) 0.01788(11) Uani 1 1 d . . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
C1 N1 1.341(3) . ?
C1 C2 1.380(4) . ?
C1 H1 0.9300 . ?
C2 C3 1.383(4) . ?
C2 H2 0.9300 . ?
C3 C4 1.385(4) . ?
C3 H3 0.9300 . ?
C4 C5 1.391(4) . ?
C4 H4 0.9300 . ?
C5 N1 1.352(3) . ?
C5 C6 1.495(4) . ?
C6 N2 1.348(3) . ?
C6 C7 1.397(4) . ?
C7 C8 1.376(4) . ?
C7 H7 0.9300 . ?
C8 C9 1.392(4) . ?
C8 H8 0.9300 . ?
C9 C10 1.380(4) . ?
C9 H9 0.9300 . ?
C10 N2 1.352(3) . ?
C10 H10 0.9300 . ?
C11 O3 1.303(3) . ?
C11 C12 1.424(4) . ?
C11 C16 1.430(3) . ?
C12 C13 1.375(4) . ?
C12 H12 0.9300 . ?
C13 C14 1.386(4) . ?
C13 H13 0.9300 . ?
C14 C15 1.386(4) . ?
C14 N3 1.455(3) . ?
C15 C16 1.401(4) . ?
C15 H15 0.9300 . ?
C16 C17 1.441(3) . ?
C17 N4 1.298(3) . ?
C17 H17 0.9300 . ?
C18 N5 1.318(3) . ?
C18 N6 1.344(3) . ?
C18 S1 1.736(2) . ?
C19 N7 1.330(3) . ?
C19 C20 1.389(4) . ?
C19 H19 0.9300 . ?
C20 C21 1.368(5) . ?
C20 H20 0.9300 . ?
C21 C22 1.368(4) . ?
C21 H21 0.9300 . ?
C22 C23 1.386(4) . ?
C22 H22 0.9300 . ?
C23 N7 1.338(3) . ?
C23 C24 1.484(4) . ?
C24 N8 1.351(4) . ?
C24 C25 1.393(4) . ?
C25 C26 1.383(4) . ?
C25 H25 0.9300 . ?
C26 C27 1.382(5) . ?
C26 H26 0.9300 . ?
C27 C28 1.384(4) . ?
C27 H27 0.9300 . ?
C28 N8 1.334(3) . ?
C28 H28 0.9300 . ?
C29 O6 1.295(3) . ?
C29 C30 1.425(4) . ?
C29 C34 1.447(3) . ?
C30 C31 1.375(4) . ?
C30 H30 0.9300 . ?
C31 C32 1.393(4) . ?
C31 H31 0.9300 . ?
C32 C33 1.393(4) . ?
C32 N9 1.442(3) . ?
C33 C34 1.398(4) . ?
C33 H33 0.9300 . ?
C34 C35 1.458(3) . ?
C35 N10 1.299(3) . ?
C35 H35 0.9300 . ?
C36 N11 1.323(3) . ?
C36 N12 1.344(4) . ?
C36 S2 1.750(3) . ?
C37 O7 1.316(3) 2_775 ?
C37 O7 1.316(3) . ?
N1 Zn1 2.127(2) . ?
N2 Zn1 2.107(2) . ?
N3 O2 1.229(3) . ?
N3 O1 1.232(3) . ?
N4 N5 1.385(3) . ?
N4 Zn1 2.089(2) . ?
N6 H6A 0.812(18) . ?
N6 H6B 0.817(18) . ?
N7 Zn2 2.058(2) . ?
N8 Zn2 2.185(2) . ?
N9 O4 1.229(3) . ?
N9 O5 1.235(3) . ?
N10 N11 1.392(3) . ?
N10 Zn2 2.107(2) . ?
N12 H12A 0.873(18) . ?
N12 H12B 0.842(18) . ?
O3 Zn1 2.0181(18) . ?
O6 Zn2 1.9923(18) . ?
S1 Zn1 2.3504(10) . ?
S2 Zn2 2.3587(10) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
N1 C1 C2 122.7(3) . . ?
N1 C1 H1 118.6 . . ?
C2 C1 H1 118.6 . . ?
C1 C2 C3 118.2(3) . . ?
C1 C2 H2 120.9 . . ?
C3 C2 H2 120.9 . . ?
C2 C3 C4 119.8(3) . . ?
C2 C3 H3 120.1 . . ?
C4 C3 H3 120.1 . . ?
C3 C4 C5 118.9(3) . . ?
C3 C4 H4 120.5 . . ?
C5 C4 H4 120.5 . . ?
N1 C5 C4 121.1(2) . . ?
N1 C5 C6 116.1(2) . . ?
C4 C5 C6 122.9(2) . . ?
N2 C6 C7 121.6(3) . . ?
N2 C6 C5 115.7(2) . . ?
C7 C6 C5 122.6(2) . . ?
C8 C7 C6 119.2(3) . . ?
C8 C7 H7 120.4 . . ?
C6 C7 H7 120.4 . . ?
C7 C8 C9 119.2(3) . . ?
C7 C8 H8 120.4 . . ?
C9 C8 H8 120.4 . . ?
C10 C9 C8 118.9(3) . . ?
C10 C9 H9 120.6 . . ?
C8 C9 H9 120.6 . . ?
N2 C10 C9 122.4(3) . . ?
N2 C10 H10 118.8 . . ?
C9 C10 H10 118.8 . . ?
O3 C11 C12 118.7(2) . . ?
O3 C11 C16 123.9(2) . . ?
C12 C11 C16 117.3(2) . . ?
C13 C12 C11 122.5(3) . . ?
C13 C12 H12 118.8 . . ?
C11 C12 H12 118.8 . . ?
C12 C13 C14 119.2(2) . . ?
C12 C13 H13 120.4 . . ?
C14 C13 H13 120.4 . . ?
C13 C14 C15 120.6(2) . . ?
C13 C14 N3 120.3(2) . . ?
C15 C14 N3 119.1(2) . . ?
C14 C15 C16 121.4(2) . . ?
C14 C15 H15 119.3 . . ?
C16 C15 H15 119.3 . . ?
C15 C16 C11 118.9(2) . . ?
C15 C16 C17 116.5(2) . . ?
C11 C16 C17 124.4(2) . . ?
N4 C17 C16 125.4(2) . . ?
N4 C17 H17 117.3 . . ?
C16 C17 H17 117.3 . . ?
N5 C18 N6 117.2(2) . . ?
N5 C18 S1 126.72(19) . . ?
N6 C18 S1 116.11(18) . . ?
N7 C19 C20 122.0(3) . . ?
N7 C19 H19 119.0 . . ?
C20 C19 H19 119.0 . . ?
C21 C20 C19 119.2(3) . . ?
C21 C20 H20 120.4 . . ?
C19 C20 H20 120.4 . . ?
C20 C21 C22 118.8(3) . . ?
C20 C21 H21 120.6 . . ?
C22 C21 H21 120.6 . . ?
C21 C22 C23 119.7(3) . . ?
C21 C22 H22 120.1 . . ?
C23 C22 H22 120.1 . . ?
N7 C23 C22 121.4(3) . . ?
N7 C23 C24 115.7(2) . . ?
C22 C23 C24 122.9(3) . . ?
N8 C24 C25 121.5(3) . . ?
N8 C24 C23 115.5(2) . . ?
C25 C24 C23 122.9(3) . . ?
C26 C25 C24 119.1(3) . . ?
C26 C25 H25 120.5 . . ?
C24 C25 H25 120.5 . . ?
C27 C26 C25 119.4(3) . . ?
C27 C26 H26 120.3 . . ?
C25 C26 H26 120.3 . . ?
C26 C27 C28 118.3(3) . . ?
C26 C27 H27 120.8 . . ?
C28 C27 H27 120.8 . . ?
N8 C28 C27 123.2(3) . . ?
N8 C28 H28 118.4 . . ?
C27 C28 H28 118.4 . . ?
O6 C29 C30 119.2(2) . . ?
O6 C29 C34 123.9(2) . . ?
C30 C29 C34 116.8(2) . . ?
C31 C30 C29 123.0(2) . . ?
C31 C30 H30 118.5 . . ?
C29 C30 H30 118.5 . . ?
C30 C31 C32 118.8(2) . . ?
C30 C31 H31 120.6 . . ?
C32 C31 H31 120.6 . . ?
C33 C32 C31 121.0(2) . . ?
C33 C32 N9 120.2(2) . . ?
C31 C32 N9 118.7(2) . . ?
C32 C33 C34 121.1(2) . . ?
C32 C33 H33 119.4 . . ?
C34 C33 H33 119.4 . . ?
C33 C34 C29 119.0(2) . . ?
C33 C34 C35 116.2(2) . . ?
C29 C34 C35 124.6(2) . . ?
N10 C35 C34 124.5(2) . . ?
N10 C35 H35 117.7 . . ?
C34 C35 H35 117.7 . . ?
N11 C36 N12 117.1(2) . . ?
N11 C36 S2 126.2(2) . . ?
N12 C36 S2 116.7(2) . . ?
O7 C37 O7 180.0(4) 2_775 . ?
C1 N1 C5 119.2(2) . . ?
C1 N1 Zn1 126.39(18) . . ?
C5 N1 Zn1 114.40(17) . . ?
C6 N2 C10 118.7(2) . . ?
C6 N2 Zn1 115.34(17) . . ?
C10 N2 Zn1 125.97(18) . . ?
O2 N3 O1 122.3(2) . . ?
O2 N3 C14 118.7(2) . . ?
O1 N3 C14 118.9(2) . . ?
C17 N4 N5 114.6(2) . . ?
C17 N4 Zn1 125.61(17) . . ?
N5 N4 Zn1 119.80(15) . . ?
C18 N5 N4 114.7(2) . . ?
C18 N6 H6A 124(2) . . ?
C18 N6 H6B 113(2) . . ?
H6A N6 H6B 122(3) . . ?
C19 N7 C23 119.0(3) . . ?
C19 N7 Zn2 123.0(2) . . ?
C23 N7 Zn2 118.04(18) . . ?
C28 N8 C24 118.5(2) . . ?
C28 N8 Zn2 127.6(2) . . ?
C24 N8 Zn2 113.18(17) . . ?
O4 N9 O5 122.1(2) . . ?
O4 N9 C32 118.7(2) . . ?
O5 N9 C32 119.1(2) . . ?
C35 N10 N11 115.3(2) . . ?
C35 N10 Zn2 126.28(17) . . ?
N11 N10 Zn2 118.28(16) . . ?
C36 N11 N10 113.6(2) . . ?
C36 N12 H12A 123(2) . . ?
C36 N12 H12B 123(2) . . ?
H12A N12 H12B 113(3) . . ?
C11 O3 Zn1 127.78(16) . . ?
C29 O6 Zn2 130.16(16) . . ?
C18 S1 Zn1 95.03(9) . . ?
C36 S2 Zn2 93.65(9) . . ?
O3 Zn1 N4 88.37(8) . . ?
O3 Zn1 N2 96.66(8) . . ?
N4 Zn1 N2 114.89(8) . . ?
O3 Zn1 N1 90.16(8) . . ?
N4 Zn1 N1 166.79(9) . . ?
N2 Zn1 N1 78.33(8) . . ?
O3 Zn1 S1 152.77(6) . . ?
N4 Zn1 S1 82.64(6) . . ?
N2 Zn1 S1 110.45(6) . . ?
N1 Zn1 S1 92.81(6) . . ?
O6 Zn2 N7 102.59(8) . . ?
O6 Zn2 N10 88.67(8) . . ?
N7 Zn2 N10 104.71(9) . . ?
O6 Zn2 N8 96.78(8) . . ?
N7 Zn2 N8 77.17(9) . . ?
N10 Zn2 N8 173.74(8) . . ?
O6 Zn2 S2 146.57(6) . . ?
N7 Zn2 S2 110.80(6) . . ?
N10 Zn2 S2 81.44(6) . . ?
N8 Zn2 S2 92.31(6) . . ?

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
N1 C1 C2 C3 1.2(4) . . . . ?
C1 C2 C3 C4 0.2(4) . . . . ?
C2 C3 C4 C5 -0.8(4) . . . . ?
C3 C4 C5 N1 0.1(4) . . . . ?
C3 C4 C5 C6 -179.1(2) . . . . ?
N1 C5 C6 N2 -3.1(3) . . . . ?
C4 C5 C6 N2 176.1(2) . . . . ?
N1 C5 C6 C7 179.1(2) . . . . ?
C4 C5 C6 C7 -1.7(4) . . . . ?
N2 C6 C7 C8 0.2(4) . . . . ?
C5 C6 C7 C8 178.0(2) . . . . ?
C6 C7 C8 C9 -0.8(4) . . . . ?
C7 C8 C9 C10 0.3(4) . . . . ?
C8 C9 C10 N2 0.9(4) . . . . ?
O3 C11 C12 C13 -179.2(3) . . . . ?
C16 C11 C12 C13 3.0(4) . . . . ?
C11 C12 C13 C14 -1.7(4) . . . . ?
C12 C13 C14 C15 -1.3(4) . . . . ?
C12 C13 C14 N3 179.1(3) . . . . ?
C13 C14 C15 C16 3.0(4) . . . . ?
N3 C14 C15 C16 -177.4(2) . . . . ?
C14 C15 C16 C11 -1.6(4) . . . . ?
C14 C15 C16 C17 -177.9(2) . . . . ?
O3 C11 C16 C15 -178.9(2) . . . . ?
C12 C11 C16 C15 -1.3(4) . . . . ?
O3 C11 C16 C17 -3.0(4) . . . . ?
C12 C11 C16 C17 174.7(3) . . . . ?
C15 C16 C17 N4 -172.9(2) . . . . ?
C11 C16 C17 N4 11.1(4) . . . . ?
N7 C19 C20 C21 -1.2(5) . . . . ?
C19 C20 C21 C22 0.1(5) . . . . ?
C20 C21 C22 C23 0.4(4) . . . . ?
C21 C22 C23 N7 0.1(4) . . . . ?
C21 C22 C23 C24 179.8(3) . . . . ?
N7 C23 C24 N8 -5.1(3) . . . . ?
C22 C23 C24 N8 175.2(2) . . . . ?
N7 C23 C24 C25 173.7(2) . . . . ?
C22 C23 C24 C25 -6.0(4) . . . . ?
N8 C24 C25 C26 0.6(4) . . . . ?
C23 C24 C25 C26 -178.1(3) . . . . ?
C24 C25 C26 C27 0.3(4) . . . . ?
C25 C26 C27 C28 -0.7(4) . . . . ?
C26 C27 C28 N8 0.4(4) . . . . ?
O6 C29 C30 C31 -174.5(2) . . . . ?
C34 C29 C30 C31 5.2(4) . . . . ?
C29 C30 C31 C32 -1.6(4) . . . . ?
C30 C31 C32 C33 -2.3(4) . . . . ?
C30 C31 C32 N9 172.9(2) . . . . ?
C31 C32 C33 C34 2.3(4) . . . . ?
N9 C32 C33 C34 -172.7(2) . . . . ?
C32 C33 C34 C29 1.4(4) . . . . ?
C32 C33 C34 C35 177.0(2) . . . . ?
O6 C29 C34 C33 174.7(2) . . . . ?
C30 C29 C34 C33 -5.0(3) . . . . ?
O6 C29 C34 C35 -0.4(4) . . . . ?
C30 C29 C34 C35 179.9(2) . . . . ?
C33 C34 C35 N10 -176.6(2) . . . . ?
C29 C34 C35 N10 -1.4(4) . . . . ?
C2 C1 N1 C5 -2.0(4) . . . . ?
C2 C1 N1 Zn1 179.05(19) . . . . ?
C4 C5 N1 C1 1.3(4) . . . . ?
C6 C5 N1 C1 -179.5(2) . . . . ?
C4 C5 N1 Zn1 -179.61(19) . . . . ?
C6 C5 N1 Zn1 -0.4(3) . . . . ?
C7 C6 N2 C10 0.9(4) . . . . ?
C5 C6 N2 C10 -177.0(2) . . . . ?
C7 C6 N2 Zn1 -177.14(19) . . . . ?
C5 C6 N2 Zn1 5.0(3) . . . . ?
C9 C10 N2 C6 -1.5(4) . . . . ?
C9 C10 N2 Zn1 176.35(19) . . . . ?
C13 C14 N3 O2 -5.2(4) . . . . ?
C15 C14 N3 O2 175.2(3) . . . . ?
C13 C14 N3 O1 176.6(3) . . . . ?
C15 C14 N3 O1 -3.0(4) . . . . ?
C16 C17 N4 N5 -176.5(2) . . . . ?
C16 C17 N4 Zn1 2.4(4) . . . . ?
N6 C18 N5 N4 178.0(2) . . . . ?
S1 C18 N5 N4 -2.5(3) . . . . ?
C17 N4 N5 C18 172.0(2) . . . . ?
Zn1 N4 N5 C18 -7.0(3) . . . . ?
C20 C19 N7 C23 1.7(4) . . . . ?
C20 C19 N7 Zn2 -179.5(2) . . . . ?
C22 C23 N7 C19 -1.1(4) . . . . ?
C24 C23 N7 C19 179.1(2) . . . . ?
C22 C23 N7 Zn2 179.97(19) . . . . ?
C24 C23 N7 Zn2 0.2(3) . . . . ?
C27 C28 N8 C24 0.4(4) . . . . ?
C27 C28 N8 Zn2 169.7(2) . . . . ?
C25 C24 N8 C28 -0.9(4) . . . . ?
C23 C24 N8 C28 177.9(2) . . . . ?
C25 C24 N8 Zn2 -171.7(2) . . . . ?
C23 C24 N8 Zn2 7.1(3) . . . . ?
C33 C32 N9 O4 -2.5(4) . . . . ?
C31 C32 N9 O4 -177.7(2) . . . . ?
C33 C32 N9 O5 174.5(2) . . . . ?
C31 C32 N9 O5 -0.7(4) . . . . ?
C34 C35 N10 N11 176.8(2) . . . . ?
C34 C35 N10 Zn2 -7.3(4) . . . . ?
N12 C36 N11 N10 -177.3(2) . . . . ?
S2 C36 N11 N10 4.9(3) . . . . ?
C35 N10 N11 C36 -166.0(2) . . . . ?
Zn2 N10 N11 C36 17.7(3) . . . . ?
C12 C11 O3 Zn1 164.11(19) . . . . ?
C16 C11 O3 Zn1 -18.3(4) . . . . ?
C30 C29 O6 Zn2 -168.50(17) . . . . ?
C34 C29 O6 Zn2 11.8(4) . . . . ?
N5 C18 S1 Zn1 8.6(2) . . . . ?
N6 C18 S1 Zn1 -171.96(19) . . . . ?
N11 C36 S2 Zn2 -20.1(2) . . . . ?
N12 C36 S2 Zn2 162.1(2) . . . . ?
C11 O3 Zn1 N4 23.0(2) . . . . ?
C11 O3 Zn1 N2 -91.9(2) . . . . ?
C11 O3 Zn1 N1 -170.1(2) . . . . ?
C11 O3 Zn1 S1 93.4(2) . . . . ?
C17 N4 Zn1 O3 -15.0(2) . . . . ?
N5 N4 Zn1 O3 163.91(18) . . . . ?
C17 N4 Zn1 N2 81.6(2) . . . . ?
N5 N4 Zn1 N2 -99.50(18) . . . . ?
C17 N4 Zn1 N1 -98.7(4) . . . . ?
N5 N4 Zn1 N1 80.2(4) . . . . ?
C17 N4 Zn1 S1 -169.2(2) . . . . ?
N5 N4 Zn1 S1 9.68(16) . . . . ?
C6 N2 Zn1 O3 -92.77(18) . . . . ?
C10 N2 Zn1 O3 89.3(2) . . . . ?
C6 N2 Zn1 N4 175.93(16) . . . . ?
C10 N2 Zn1 N4 -1.9(2) . . . . ?
C6 N2 Zn1 N1 -3.99(17) . . . . ?
C10 N2 Zn1 N1 178.1(2) . . . . ?
C6 N2 Zn1 S1 84.65(17) . . . . ?
C10 N2 Zn1 S1 -93.2(2) . . . . ?
C1 N1 Zn1 O3 -81.9(2) . . . . ?
C5 N1 Zn1 O3 99.03(18) . . . . ?
C1 N1 Zn1 N4 1.6(5) . . . . ?
C5 N1 Zn1 N4 -177.4(3) . . . . ?
C1 N1 Zn1 N2 -178.7(2) . . . . ?
C5 N1 Zn1 N2 2.26(17) . . . . ?
C1 N1 Zn1 S1 71.0(2) . . . . ?
C5 N1 Zn1 S1 -108.05(17) . . . . ?
C18 S1 Zn1 O3 -79.63(14) . . . . ?
C18 S1 Zn1 N4 -7.91(10) . . . . ?
C18 S1 Zn1 N2 105.97(10) . . . . ?
C18 S1 Zn1 N1 -175.45(10) . . . . ?
C29 O6 Zn2 N7 89.9(2) . . . . ?
C29 O6 Zn2 N10 -14.9(2) . . . . ?
C29 O6 Zn2 N8 168.2(2) . . . . ?
C29 O6 Zn2 S2 -87.1(2) . . . . ?
C19 N7 Zn2 O6 -82.0(2) . . . . ?
C23 N7 Zn2 O6 96.86(19) . . . . ?
C19 N7 Zn2 N10 10.0(2) . . . . ?
C23 N7 Zn2 N10 -171.18(18) . . . . ?
C19 N7 Zn2 N8 -176.2(2) . . . . ?
C23 N7 Zn2 N8 2.66(18) . . . . ?
C19 N7 Zn2 S2 96.2(2) . . . . ?
C23 N7 Zn2 S2 -84.91(19) . . . . ?
C35 N10 Zn2 O6 12.4(2) . . . . ?
N11 N10 Zn2 O6 -171.85(18) . . . . ?
C35 N10 Zn2 N7 -90.3(2) . . . . ?
N11 N10 Zn2 N7 85.49(18) . . . . ?
C35 N10 Zn2 S2 160.3(2) . . . . ?
N11 N10 Zn2 S2 -23.89(16) . . . . ?
C28 N8 Zn2 O6 83.4(2) . . . . ?
C24 N8 Zn2 O6 -106.77(18) . . . . ?
C28 N8 Zn2 N7 -175.1(2) . . . . ?
C24 N8 Zn2 N7 -5.35(17) . . . . ?
C28 N8 Zn2 S2 -64.3(2) . . . . ?
C24 N8 Zn2 S2 105.46(17) . . . . ?
C36 S2 Zn2 O6 93.31(13) . . . . ?
C36 S2 Zn2 N7 -83.55(11) . . . . ?
C36 S2 Zn2 N10 19.01(10) . . . . ?
C36 S2 Zn2 N8 -160.70(10) . . . . ?

_diffrn_measured_fraction_theta_max 0.981
_diffrn_reflns_theta_full        26.42
_diffrn_measured_fraction_theta_full 0.981
_refine_diff_density_max         0.983
_refine_diff_density_min         -0.666
_refine_diff_density_rms         0.116
# start Validation Reply Form
_vrf_PLAT041_shelxl              
;
RESPONSE: This Alert is due to the absence of 
protons of highly disordered lattice methanol molecule. 
;
_vrf_PLAT068_shelxl              
;
RESPONSE: This Alert is due to the absence of 
protons of highly disordered lattice methanol molecule. 
;
_vrf_PLAT430_shelxl              
;
RESPONSE: This Alert is due to the absence of 
protons of highly disordered lattice methanol molecule. 
;
# end Validation Reply Form  

####################################################################### 
# 
# 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 1427482'
_audit_update_record             
;
2016-02-01 deposited with the CCDC.
2016-02-17 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C21 H16 N6 O3 S Zn'
_chemical_formula_sum            'C21 H16 N6 O3 S Zn'
_chemical_formula_weight         497.86

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'
S S 0.1246 0.1234 '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                   6.0475(6)
_cell_length_b                   12.1271(11)
_cell_length_c                   14.1409(15)
_cell_angle_alpha                86.254(3)
_cell_angle_beta                 82.737(4)
_cell_angle_gamma                81.271(3)
_cell_volume                     1015.71(17)
_cell_formula_units_Z            2
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    5626
_cell_measurement_theta_min      2.18
_cell_measurement_theta_max      27.44

_exptl_crystal_description       Prism
_exptl_crystal_colour            Yellow
_exptl_crystal_size_max          0.11
_exptl_crystal_size_mid          0.08
_exptl_crystal_size_min          0.05
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.628
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             508
_exptl_absorpt_coefficient_mu    1.351
_exptl_absorpt_correction_type   Multi-scan
_exptl_absorpt_correction_T_min  0.6625
_exptl_absorpt_correction_T_max  0.7457
_exptl_absorpt_process_details   
'SADABS-2014/5 - Bruker AXS area detector scaling and absorption correction'

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      296(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            16500
_diffrn_reflns_av_R_equivalents  0.0387
_diffrn_reflns_av_sigmaI/netI    0.0436
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_theta_min         2.18
_diffrn_reflns_theta_max         28.62
_reflns_number_total             4993
_reflns_number_gt                3818
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick 2008)'
_computing_structure_refinement  'SHELXL-2014 (Sheldrick 2014)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'

_refine_special_details          
; 
 Refinement of F² against ALL reflections.  The weighted R-factor wR and 
 goodness of fit S are based on F², conventional R-factors R are based 
 on F, with F set to zero for negative F². The threshold expression of 
 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is 
 not relevant to the choice of reflections for refinement.  R-factors based 
 on F² are statistically about twice as large as those based on F, and R- 
 factors based on ALL data will be even larger. 
;

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0553P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    none
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         4993
_refine_ls_number_parameters     290
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0552
_refine_ls_R_factor_gt           0.0365
_refine_ls_wR_factor_ref         0.0972
_refine_ls_wR_factor_gt          0.0885
_refine_ls_goodness_of_fit_ref   0.987
_refine_ls_restrained_S_all      0.987
_refine_ls_shift/su_max          0.021
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C -0.0750(4) 0.3871(2) 0.40251(19) 0.0493(6) Uani 1 1 d . . .
H1 H -0.1218 0.3375 0.4513 0.059 Uiso 1 1 calc R . .
C2 C -0.2174(4) 0.4870(2) 0.3852(2) 0.0625(8) Uani 1 1 d . . .
H2 H -0.3560 0.5030 0.4221 0.075 Uiso 1 1 calc R . .
C3 C -0.1517(5) 0.5595(2) 0.3150(2) 0.0629(8) Uani 1 1 d . . .
H3 H -0.2450 0.6261 0.3035 0.075 Uiso 1 1 calc R . .
C4 C 0.0564(4) 0.53525(19) 0.25889(19) 0.0467(6) Uani 1 1 d . . .
C5 C 0.1368(6) 0.6048(2) 0.1813(2) 0.0639(8) Uani 1 1 d . . .
H5 H 0.0463 0.6703 0.1643 0.077 Uiso 1 1 calc R . .
C6 C 0.3407(6) 0.5779(2) 0.1319(2) 0.0661(9) Uani 1 1 d . . .
H6 H 0.3874 0.6251 0.0813 0.079 Uiso 1 1 calc R . .
C7 C 0.4883(5) 0.4784(2) 0.15503(17) 0.0486(6) Uani 1 1 d . . .
C8 C 0.7074(5) 0.4470(3) 0.10938(19) 0.0649(9) Uani 1 1 d . . .
H8 H 0.7650 0.4918 0.0592 0.078 Uiso 1 1 calc R . .
C9 C 0.8348(4) 0.3523(3) 0.1379(2) 0.0626(8) Uani 1 1 d . . .
H9 H 0.9804 0.3325 0.1083 0.075 Uiso 1 1 calc R . .
C10 C 0.7462(4) 0.2843(2) 0.21238(18) 0.0487(6) Uani 1 1 d . . .
H10 H 0.8351 0.2193 0.2316 0.058 Uiso 1 1 calc R . .
C11 C 0.4122(4) 0.40502(18) 0.22934(15) 0.0344(5) Uani 1 1 d . . .
C12 C 0.1915(3) 0.43378(17) 0.28194(16) 0.0338(5) Uani 1 1 d . . .
C13 C 0.3019(3) 0.05256(18) 0.22155(16) 0.0338(5) Uani 1 1 d . . .
C14 C 0.1838(4) 0.0247(2) 0.14720(17) 0.0420(6) Uani 1 1 d . . .
H14 H 0.0402 0.0628 0.1416 0.050 Uiso 1 1 calc R . .
C15 C 0.2724(4) -0.0553(2) 0.08413(17) 0.0419(5) Uani 1 1 d . . .
H15 H 0.1911 -0.0709 0.0363 0.050 Uiso 1 1 calc R . .
C16 C 0.4881(4) -0.11365(18) 0.09263(16) 0.0377(5) Uani 1 1 d . . .
C17 C 0.6064(4) -0.09277(18) 0.16496(16) 0.0361(5) Uani 1 1 d . . .
H17 H 0.7477 -0.1338 0.1702 0.043 Uiso 1 1 calc R . .
C18 C 0.5194(3) -0.01151(17) 0.23064(15) 0.0329(5) Uani 1 1 d . . .
C19 C 0.6513(3) -0.00342(18) 0.30719(16) 0.0355(5) Uani 1 1 d . . .
H19 H 0.7790 -0.0561 0.3111 0.043 Uiso 1 1 calc R . .
C20 C 0.6911(3) 0.13485(17) 0.50672(15) 0.0321(5) Uani 1 1 d . . .
C21 C 0.8161(4) 0.2062(2) 0.64810(17) 0.0474(6) Uani 1 1 d . . .
H21A H 0.6819 0.2595 0.6461 0.071 Uiso 1 1 calc R . .
H21B H 0.9453 0.2446 0.6397 0.071 Uiso 1 1 calc R . .
H21C H 0.8100 0.1654 0.7087 0.071 Uiso 1 1 calc R . .
N1 N 0.1249(3) 0.36050(15) 0.35156(13) 0.0349(4) Uani 1 1 d . . .
N2 N 0.5386(3) 0.30975(15) 0.25672(13) 0.0353(4) Uani 1 1 d . . .
N3 N 0.5871(4) -0.19754(17) 0.02597(15) 0.0458(5) Uani 1 1 d . . .
N4 N 0.6071(3) 0.07068(14) 0.37062(13) 0.0325(4) Uani 1 1 d . . .
N5 N 0.7511(3) 0.06133(15) 0.43959(13) 0.0348(4) Uani 1 1 d . . .
N6 N 0.8327(3) 0.13001(17) 0.57299(14) 0.0460(5) Uani 1 1 d . . .
H6A H 0.9438 0.0764 0.5703 0.055 Uiso 1 1 calc R . .
O1 O 0.2097(2) 0.13171(13) 0.27692(12) 0.0422(4) Uani 1 1 d . . .
O2 O 0.4823(3) -0.21437(17) -0.03908(13) 0.0636(5) Uani 1 1 d . . .
O3 O 0.7729(3) -0.25033(17) 0.03704(14) 0.0685(6) Uani 1 1 d . . .
S1 S 0.44974(9) 0.23522(5) 0.51595(4) 0.03948(15) Uani 1 1 d . . .
Zn1 Zn 0.36589(4) 0.21059(2) 0.362426(18) 0.03482(10) Uani 1 1 d . . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
C1 N1 1.333(3) . ?
C1 C2 1.403(4) . ?
C1 H1 0.9300 . ?
C2 C3 1.346(4) . ?
C2 H2 0.9300 . ?
C3 C4 1.402(4) . ?
C3 H3 0.9300 . ?
C4 C12 1.413(3) . ?
C4 C5 1.421(4) . ?
C5 C6 1.343(4) . ?
C5 H5 0.9300 . ?
C6 C7 1.433(4) . ?
C6 H6 0.9300 . ?
C7 C8 1.407(4) . ?
C7 C11 1.410(3) . ?
C8 C9 1.351(4) . ?
C8 H8 0.9300 . ?
C9 C10 1.398(4) . ?
C9 H9 0.9300 . ?
C10 N2 1.332(3) . ?
C10 H10 0.9300 . ?
C11 N2 1.348(3) . ?
C11 C12 1.448(3) . ?
C12 N1 1.347(3) . ?
C13 O1 1.293(2) . ?
C13 C14 1.428(3) . ?
C13 C18 1.438(3) . ?
C14 C15 1.363(3) . ?
C14 H14 0.9300 . ?
C15 C16 1.402(3) . ?
C15 H15 0.9300 . ?
C16 C17 1.377(3) . ?
C16 N3 1.442(3) . ?
C17 C18 1.396(3) . ?
C17 H17 0.9300 . ?
C18 C19 1.440(3) . ?
C19 N4 1.287(3) . ?
C19 H19 0.9300 . ?
C20 N5 1.324(3) . ?
C20 N6 1.340(3) . ?
C20 S1 1.750(2) . ?
C21 N6 1.437(3) . ?
C21 H21A 0.9600 . ?
C21 H21B 0.9600 . ?
C21 H21C 0.9600 . ?
N1 Zn1 2.1606(17) . ?
N2 Zn1 2.1267(18) . ?
N3 O2 1.225(3) . ?
N3 O3 1.229(3) . ?
N4 N5 1.375(2) . ?
N4 Zn1 2.0703(17) . ?
N6 H6A 0.8600 . ?
O1 Zn1 1.9958(15) . ?
S1 Zn1 2.3385(7) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
N1 C1 C2 122.4(3) . . ?
N1 C1 H1 118.8 . . ?
C2 C1 H1 118.8 . . ?
C3 C2 C1 119.4(2) . . ?
C3 C2 H2 120.3 . . ?
C1 C2 H2 120.3 . . ?
C2 C3 C4 120.4(2) . . ?
C2 C3 H3 119.8 . . ?
C4 C3 H3 119.8 . . ?
C3 C4 C12 116.6(2) . . ?
C3 C4 C5 124.5(3) . . ?
C12 C4 C5 118.9(2) . . ?
C6 C5 C4 121.4(3) . . ?
C6 C5 H5 119.3 . . ?
C4 C5 H5 119.3 . . ?
C5 C6 C7 121.9(3) . . ?
C5 C6 H6 119.1 . . ?
C7 C6 H6 119.1 . . ?
C8 C7 C11 116.3(3) . . ?
C8 C7 C6 125.1(3) . . ?
C11 C7 C6 118.6(2) . . ?
C9 C8 C7 120.5(3) . . ?
C9 C8 H8 119.8 . . ?
C7 C8 H8 119.8 . . ?
C8 C9 C10 119.5(2) . . ?
C8 C9 H9 120.2 . . ?
C10 C9 H9 120.2 . . ?
N2 C10 C9 122.1(3) . . ?
N2 C10 H10 119.0 . . ?
C9 C10 H10 119.0 . . ?
N2 C11 C7 123.1(2) . . ?
N2 C11 C12 117.50(19) . . ?
C7 C11 C12 119.4(2) . . ?
N1 C12 C4 123.0(2) . . ?
N1 C12 C11 117.26(18) . . ?
C4 C12 C11 119.7(2) . . ?
O1 C13 C14 119.33(18) . . ?
O1 C13 C18 123.70(19) . . ?
C14 C13 C18 116.97(19) . . ?
C15 C14 C13 122.8(2) . . ?
C15 C14 H14 118.6 . . ?
C13 C14 H14 118.6 . . ?
C14 C15 C16 118.9(2) . . ?
C14 C15 H15 120.6 . . ?
C16 C15 H15 120.6 . . ?
C17 C16 C15 120.7(2) . . ?
C17 C16 N3 119.3(2) . . ?
C15 C16 N3 120.0(2) . . ?
C16 C17 C18 121.6(2) . . ?
C16 C17 H17 119.2 . . ?
C18 C17 H17 119.2 . . ?
C17 C18 C13 119.0(2) . . ?
C17 C18 C19 116.30(18) . . ?
C13 C18 C19 124.61(19) . . ?
N4 C19 C18 125.42(19) . . ?
N4 C19 H19 117.3 . . ?
C18 C19 H19 117.3 . . ?
N5 C20 N6 115.24(18) . . ?
N5 C20 S1 126.43(16) . . ?
N6 C20 S1 118.33(16) . . ?
N6 C21 H21A 109.5 . . ?
N6 C21 H21B 109.5 . . ?
H21A C21 H21B 109.5 . . ?
N6 C21 H21C 109.5 . . ?
H21A C21 H21C 109.5 . . ?
H21B C21 H21C 109.5 . . ?
C1 N1 C12 118.1(2) . . ?
C1 N1 Zn1 128.81(17) . . ?
C12 N1 Zn1 113.11(13) . . ?
C10 N2 C11 118.5(2) . . ?
C10 N2 Zn1 127.37(18) . . ?
C11 N2 Zn1 113.93(13) . . ?
O2 N3 O3 122.3(2) . . ?
O2 N3 C16 118.9(2) . . ?
O3 N3 C16 118.7(2) . . ?
C19 N4 N5 116.15(17) . . ?
C19 N4 Zn1 123.60(15) . . ?
N5 N4 Zn1 119.68(13) . . ?
C20 N5 N4 114.06(16) . . ?
C20 N6 C21 125.98(19) . . ?
C20 N6 H6A 117.0 . . ?
C21 N6 H6A 117.0 . . ?
C13 O1 Zn1 126.32(13) . . ?
C20 S1 Zn1 93.96(7) . . ?
O1 Zn1 N4 89.63(6) . . ?
O1 Zn1 N2 98.62(7) . . ?
N4 Zn1 N2 100.18(7) . . ?
O1 Zn1 N1 91.58(6) . . ?
N4 Zn1 N1 177.66(7) . . ?
N2 Zn1 N1 77.67(7) . . ?
O1 Zn1 S1 149.04(5) . . ?
N4 Zn1 S1 83.01(5) . . ?
N2 Zn1 S1 112.27(5) . . ?
N1 Zn1 S1 96.94(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
N1 C1 C2 C3 -0.1(4) . . . . ?
C1 C2 C3 C4 0.4(4) . . . . ?
C2 C3 C4 C12 -1.5(4) . . . . ?
C2 C3 C4 C5 177.9(3) . . . . ?
C3 C4 C5 C6 178.3(3) . . . . ?
C12 C4 C5 C6 -2.3(4) . . . . ?
C4 C5 C6 C7 -0.4(4) . . . . ?
C5 C6 C7 C8 -177.2(3) . . . . ?
C5 C6 C7 C11 2.6(4) . . . . ?
C11 C7 C8 C9 -1.1(4) . . . . ?
C6 C7 C8 C9 178.7(3) . . . . ?
C7 C8 C9 C10 1.0(4) . . . . ?
C8 C9 C10 N2 0.0(4) . . . . ?
C8 C7 C11 N2 0.1(3) . . . . ?
C6 C7 C11 N2 -179.7(2) . . . . ?
C8 C7 C11 C12 177.8(2) . . . . ?
C6 C7 C11 C12 -2.0(3) . . . . ?
C3 C4 C12 N1 2.3(3) . . . . ?
C5 C4 C12 N1 -177.1(2) . . . . ?
C3 C4 C12 C11 -177.8(2) . . . . ?
C5 C4 C12 C11 2.8(3) . . . . ?
N2 C11 C12 N1 -3.0(3) . . . . ?
C7 C11 C12 N1 179.2(2) . . . . ?
N2 C11 C12 C4 177.15(19) . . . . ?
C7 C11 C12 C4 -0.7(3) . . . . ?
O1 C13 C14 C15 178.0(2) . . . . ?
C18 C13 C14 C15 -2.7(3) . . . . ?
C13 C14 C15 C16 0.5(4) . . . . ?
C14 C15 C16 C17 1.7(3) . . . . ?
C14 C15 C16 N3 -179.1(2) . . . . ?
C15 C16 C17 C18 -1.6(3) . . . . ?
N3 C16 C17 C18 179.2(2) . . . . ?
C16 C17 C18 C13 -0.7(3) . . . . ?
C16 C17 C18 C19 175.4(2) . . . . ?
O1 C13 C18 C17 -177.9(2) . . . . ?
C14 C13 C18 C17 2.7(3) . . . . ?
O1 C13 C18 C19 6.3(3) . . . . ?
C14 C13 C18 C19 -173.0(2) . . . . ?
C17 C18 C19 N4 175.1(2) . . . . ?
C13 C18 C19 N4 -9.1(4) . . . . ?
C2 C1 N1 C12 0.8(4) . . . . ?
C2 C1 N1 Zn1 -177.99(18) . . . . ?
C4 C12 N1 C1 -2.0(3) . . . . ?
C11 C12 N1 C1 178.1(2) . . . . ?
C4 C12 N1 Zn1 177.00(16) . . . . ?
C11 C12 N1 Zn1 -2.9(2) . . . . ?
C9 C10 N2 C11 -0.9(3) . . . . ?
C9 C10 N2 Zn1 174.31(17) . . . . ?
C7 C11 N2 C10 0.9(3) . . . . ?
C12 C11 N2 C10 -176.82(19) . . . . ?
C7 C11 N2 Zn1 -174.97(17) . . . . ?
C12 C11 N2 Zn1 7.3(2) . . . . ?
C17 C16 N3 O2 -178.8(2) . . . . ?
C15 C16 N3 O2 2.0(3) . . . . ?
C17 C16 N3 O3 1.8(3) . . . . ?
C15 C16 N3 O3 -177.4(2) . . . . ?
C18 C19 N4 N5 177.9(2) . . . . ?
C18 C19 N4 Zn1 -10.8(3) . . . . ?
N6 C20 N5 N4 -177.80(19) . . . . ?
S1 C20 N5 N4 2.1(3) . . . . ?
C19 N4 N5 C20 -175.91(19) . . . . ?
Zn1 N4 N5 C20 12.5(2) . . . . ?
N5 C20 N6 C21 174.4(2) . . . . ?
S1 C20 N6 C21 -5.5(3) . . . . ?
C14 C13 O1 Zn1 -163.68(15) . . . . ?
C18 C13 O1 Zn1 17.0(3) . . . . ?
N5 C20 S1 Zn1 -12.2(2) . . . . ?
N6 C20 S1 Zn1 167.63(17) . . . . ?
C13 O1 Zn1 N4 -26.57(18) . . . . ?
C13 O1 Zn1 N2 73.67(18) . . . . ?
C13 O1 Zn1 N1 151.44(18) . . . . ?
C13 O1 Zn1 S1 -102.24(18) . . . . ?
C19 N4 Zn1 O1 23.18(18) . . . . ?
N5 N4 Zn1 O1 -165.89(15) . . . . ?
C19 N4 Zn1 N2 -75.51(18) . . . . ?
N5 N4 Zn1 N2 95.42(15) . . . . ?
C19 N4 Zn1 S1 173.03(18) . . . . ?
N5 N4 Zn1 S1 -16.04(14) . . . . ?
C10 N2 Zn1 O1 -92.27(19) . . . . ?
C11 N2 Zn1 O1 83.15(15) . . . . ?
C10 N2 Zn1 N4 -1.1(2) . . . . ?
C11 N2 Zn1 N4 174.33(14) . . . . ?
C10 N2 Zn1 N1 178.0(2) . . . . ?
C11 N2 Zn1 N1 -6.59(14) . . . . ?
C10 N2 Zn1 S1 85.46(19) . . . . ?
C11 N2 Zn1 S1 -99.12(14) . . . . ?
C1 N1 Zn1 O1 85.4(2) . . . . ?
C12 N1 Zn1 O1 -93.46(15) . . . . ?
C1 N1 Zn1 N2 -176.1(2) . . . . ?
C12 N1 Zn1 N2 5.02(14) . . . . ?
C1 N1 Zn1 S1 -64.8(2) . . . . ?
C12 N1 Zn1 S1 116.37(14) . . . . ?
C20 S1 Zn1 O1 89.68(11) . . . . ?
C20 S1 Zn1 N4 12.22(9) . . . . ?
C20 S1 Zn1 N2 -85.95(9) . . . . ?
C20 S1 Zn1 N1 -165.43(9) . . . . ?

_diffrn_measured_fraction_theta_max 0.959
_diffrn_reflns_theta_full        28.62
_diffrn_measured_fraction_theta_full 0.959
_refine_diff_density_max         0.326
_refine_diff_density_min         -0.300
_refine_diff_density_rms         0.062
####################################################################### 
# 
# 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 1427483'
_audit_update_record             
;
2016-02-01 deposited with the CCDC.
2016-02-17 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C20 H18 N6 O3 S Zn'
_chemical_formula_sum            'C20 H18 N6 O3 S Zn'
_chemical_formula_weight         487.86

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'
S S 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Zn Zn 0.2839 1.4301 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_symmetry_cell_setting           Monoclinic
_symmetry_space_group_name_H-M   'C 2/c'
_symmetry_space_group_name_Hall  '-C 2yc'

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

_cell_length_a                   22.2366(8)
_cell_length_b                   12.0486(5)
_cell_length_c                   17.9814(6)
_cell_angle_alpha                90.00
_cell_angle_beta                 114.9940(12)
_cell_angle_gamma                90.00
_cell_volume                     4366.4(3)
_cell_formula_units_Z            8
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    7518
_cell_measurement_theta_min      2.46
_cell_measurement_theta_max      28.36

_exptl_crystal_description       Prism
_exptl_crystal_colour            colorless
_exptl_crystal_size_max          0.12
_exptl_crystal_size_mid          0.10
_exptl_crystal_size_min          0.08
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.484
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             2000
_exptl_absorpt_coefficient_mu    1.255
_exptl_absorpt_correction_type   Multi-scan
_exptl_absorpt_correction_T_min  0.6889
_exptl_absorpt_correction_T_max  0.7461
_exptl_absorpt_process_details   
'SADABS-2008/1 - Bruker AXS area detector scaling and absorption correction'

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      296(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            25703
_diffrn_reflns_av_R_equivalents  0.0263
_diffrn_reflns_av_sigmaI/netI    0.0283
_diffrn_reflns_limit_h_min       -31
_diffrn_reflns_limit_h_max       30
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_l_min       -25
_diffrn_reflns_limit_l_max       25
_diffrn_reflns_theta_min         1.97
_diffrn_reflns_theta_max         30.33
_reflns_number_total             6523
_reflns_number_gt                4739
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'Sir-92 (Altomare et al., 1993)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'

_refine_special_details          
; 
 Refinement of F² against ALL reflections.  The weighted R-factor wR and 
 goodness of fit S are based on F², conventional R-factors R are based 
 on F, with F set to zero for negative F². The threshold expression of 
 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is 
 not relevant to the choice of reflections for refinement.  R-factors based 
 on F² are statistically about twice as large as those based on F, and R- 
 factors based on ALL data will be even larger. 
;

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0472P)²+1.6009P] 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         6523
_refine_ls_number_parameters     284
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0561
_refine_ls_R_factor_gt           0.0334
_refine_ls_wR_factor_ref         0.0942
_refine_ls_wR_factor_gt          0.0844
_refine_ls_goodness_of_fit_ref   1.028
_refine_ls_restrained_S_all      1.028
_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
C1 C 0.17629(12) -0.29740(17) 0.31807(14) 0.0530(5) Uani 1 1 d . . .
H1 H 0.1849 -0.2931 0.2718 0.064 Uiso 1 1 calc R . .
C2 C 0.15753(12) -0.39772(18) 0.33751(16) 0.0632(6) Uani 1 1 d . . .
H2 H 0.1527 -0.4598 0.3047 0.076 Uiso 1 1 calc R . .
C3 C 0.14608(11) -0.40417(19) 0.40639(16) 0.0619(6) Uani 1 1 d . . .
H3 H 0.1338 -0.4713 0.4215 0.074 Uiso 1 1 calc R . .
C4 C 0.15283(10) -0.31053(17) 0.45334(13) 0.0496(5) Uani 1 1 d . . .
H4 H 0.1455 -0.3140 0.5006 0.060 Uiso 1 1 calc R . .
C5 C 0.17056(8) -0.21151(15) 0.42935(11) 0.0354(4) Uani 1 1 d . . .
C6 C 0.17884(8) -0.10598(16) 0.47542(10) 0.0362(4) Uani 1 1 d . . .
C7 C 0.16671(11) -0.0959(2) 0.54459(13) 0.0572(6) Uani 1 1 d . . .
H7 H 0.1513 -0.1564 0.5637 0.069 Uiso 1 1 calc R . .
C8 C 0.17763(13) 0.0043(3) 0.58481(14) 0.0668(7) Uani 1 1 d . . .
H8 H 0.1701 0.0120 0.6316 0.080 Uiso 1 1 calc R . .
C9 C 0.19974(11) 0.0929(2) 0.55537(13) 0.0573(6) Uani 1 1 d . . .
H9 H 0.2075 0.1613 0.5817 0.069 Uiso 1 1 calc R . .
C10 C 0.21015(10) 0.07803(17) 0.48595(12) 0.0460(4) Uani 1 1 d . . .
H10 H 0.2254 0.1378 0.4659 0.055 Uiso 1 1 calc R . .
C11 C 0.08415(10) 0.05380(15) 0.21245(11) 0.0402(4) Uani 1 1 d . . .
C12 C 0.01519(11) 0.04281(18) 0.16293(14) 0.0547(5) Uani 1 1 d . . .
H12 H -0.0028 -0.0279 0.1489 0.066 Uiso 1 1 calc R . .
C13 C -0.02571(11) 0.1327(2) 0.13518(14) 0.0585(6) Uani 1 1 d . . .
H13 H -0.0710 0.1230 0.1041 0.070 Uiso 1 1 calc R . .
C14 C 0.00089(11) 0.23825(19) 0.15383(14) 0.0536(5) Uani 1 1 d . . .
C15 C 0.06755(10) 0.25438(17) 0.19845(13) 0.0472(5) Uani 1 1 d . . .
H15 H 0.0845 0.3262 0.2082 0.057 Uiso 1 1 calc R . .
C16 C 0.11044(9) 0.16448(15) 0.22952(11) 0.0380(4) Uani 1 1 d . . .
C17 C 0.18050(9) 0.18981(15) 0.27455(11) 0.0384(4) Uani 1 1 d . . .
H17 H 0.1938 0.2632 0.2758 0.046 Uiso 1 1 calc R . .
C18 C 0.33313(10) 0.07368(16) 0.36347(11) 0.0411(4) Uani 1 1 d . . .
C19 C 0.42194(12) 0.2153(2) 0.41247(18) 0.0693(7) Uani 1 1 d . . .
H19A H 0.4103 0.2451 0.4548 0.083 Uiso 1 1 calc R . .
H19B H 0.4010 0.2610 0.3638 0.083 Uiso 1 1 calc R . .
C20 C 0.49571(14) 0.2187(3) 0.4412(3) 0.1098(12) Uani 1 1 d . . .
H20A H 0.5161 0.1668 0.4853 0.165 Uiso 1 1 calc R . .
H20B H 0.5116 0.2922 0.4601 0.165 Uiso 1 1 calc R . .
H20C H 0.5067 0.1995 0.3967 0.165 Uiso 1 1 calc R . .
N1 N 0.18283(8) -0.20562(12) 0.36249(9) 0.0380(3) Uani 1 1 d . . .
N2 N 0.19931(7) -0.01889(12) 0.44596(9) 0.0362(3) Uani 1 1 d . . .
N3 N 0.22496(7) 0.11760(12) 0.31255(9) 0.0348(3) Uani 1 1 d . . .
N4 N 0.29006(7) 0.15497(13) 0.34705(9) 0.0397(3) Uani 1 1 d . . .
N5 N -0.04226(11) 0.3343(2) 0.12471(16) 0.0776(7) Uani 1 1 d . . .
N6 N 0.39782(9) 0.10191(17) 0.39379(13) 0.0573(5) Uani 1 1 d D . .
H6A H 0.4268(11) 0.0516(17) 0.4052(16) 0.069 Uiso 1 1 d D . .
O1 O 0.11959(7) -0.03463(11) 0.23902(9) 0.0482(3) Uani 1 1 d . . .
O2 O -0.10236(9) 0.31921(18) 0.09373(14) 0.0924(7) Uani 1 1 d . . .
O3 O -0.01665(12) 0.42640(19) 0.1308(2) 0.1292(11) Uani 1 1 d . . .
S1 S 0.31585(3) -0.06815(4) 0.34627(4) 0.04754(13) Uani 1 1 d . . .
Zn1 Zn 0.207522(11) -0.047182(16) 0.333855(12) 0.03550(7) Uani 1 1 d . . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
C1 N1 1.336(2) . ?
C1 C2 1.371(3) . ?
C1 H1 0.9300 . ?
C2 C3 1.368(4) . ?
C2 H2 0.9300 . ?
C3 C4 1.379(3) . ?
C3 H3 0.9300 . ?
C4 C5 1.381(3) . ?
C4 H4 0.9300 . ?
C5 N1 1.342(2) . ?
C5 C6 1.486(3) . ?
C6 N2 1.339(2) . ?
C6 C7 1.385(3) . ?
C7 C8 1.376(4) . ?
C7 H7 0.9300 . ?
C8 C9 1.371(4) . ?
C8 H8 0.9300 . ?
C9 C10 1.374(3) . ?
C9 H9 0.9300 . ?
C10 N2 1.339(2) . ?
C10 H10 0.9300 . ?
C11 O1 1.291(2) . ?
C11 C12 1.417(3) . ?
C11 C16 1.436(3) . ?
C12 C13 1.366(3) . ?
C12 H12 0.9300 . ?
C13 C14 1.383(3) . ?
C13 H13 0.9300 . ?
C14 C15 1.369(3) . ?
C14 N5 1.452(3) . ?
C15 C16 1.394(3) . ?
C15 H15 0.9300 . ?
C16 C17 1.453(3) . ?
C17 N3 1.277(2) . ?
C17 H17 0.9300 . ?
C18 N4 1.313(2) . ?
C18 N6 1.349(3) . ?
C18 S1 1.750(2) . ?
C19 N6 1.454(3) . ?
C19 C20 1.498(3) . ?
C19 H19A 0.9700 . ?
C19 H19B 0.9700 . ?
C20 H20A 0.9600 . ?
C20 H20B 0.9600 . ?
C20 H20C 0.9600 . ?
N1 Zn1 2.1094(15) . ?
N2 Zn1 2.1270(14) . ?
N3 N4 1.387(2) . ?
N3 Zn1 2.0891(14) . ?
N5 O2 1.225(3) . ?
N5 O3 1.231(3) . ?
N6 H6A 0.844(16) . ?
O1 Zn1 1.9840(14) . ?
S1 Zn1 2.3370(6) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
N1 C1 C2 123.0(2) . . ?
N1 C1 H1 118.5 . . ?
C2 C1 H1 118.5 . . ?
C3 C2 C1 118.3(2) . . ?
C3 C2 H2 120.9 . . ?
C1 C2 H2 120.9 . . ?
C2 C3 C4 119.6(2) . . ?
C2 C3 H3 120.2 . . ?
C4 C3 H3 120.2 . . ?
C3 C4 C5 119.1(2) . . ?
C3 C4 H4 120.4 . . ?
C5 C4 H4 120.4 . . ?
N1 C5 C4 121.21(18) . . ?
N1 C5 C6 115.45(15) . . ?
C4 C5 C6 123.33(17) . . ?
N2 C6 C7 120.96(18) . . ?
N2 C6 C5 115.65(15) . . ?
C7 C6 C5 123.39(18) . . ?
C8 C7 C6 119.4(2) . . ?
C8 C7 H7 120.3 . . ?
C6 C7 H7 120.3 . . ?
C9 C8 C7 119.5(2) . . ?
C9 C8 H8 120.2 . . ?
C7 C8 H8 120.2 . . ?
C8 C9 C10 118.3(2) . . ?
C8 C9 H9 120.8 . . ?
C10 C9 H9 120.8 . . ?
N2 C10 C9 122.7(2) . . ?
N2 C10 H10 118.6 . . ?
C9 C10 H10 118.6 . . ?
O1 C11 C12 119.00(18) . . ?
O1 C11 C16 123.89(17) . . ?
C12 C11 C16 117.10(17) . . ?
C13 C12 C11 122.2(2) . . ?
C13 C12 H12 118.9 . . ?
C11 C12 H12 118.9 . . ?
C12 C13 C14 119.3(2) . . ?
C12 C13 H13 120.3 . . ?
C14 C13 H13 120.3 . . ?
C15 C14 C13 121.27(19) . . ?
C15 C14 N5 119.0(2) . . ?
C13 C14 N5 119.7(2) . . ?
C14 C15 C16 120.8(2) . . ?
C14 C15 H15 119.6 . . ?
C16 C15 H15 119.6 . . ?
C15 C16 C11 119.21(17) . . ?
C15 C16 C17 116.81(17) . . ?
C11 C16 C17 123.91(16) . . ?
N3 C17 C16 124.11(16) . . ?
N3 C17 H17 117.9 . . ?
C16 C17 H17 117.9 . . ?
N4 C18 N6 117.04(18) . . ?
N4 C18 S1 127.14(15) . . ?
N6 C18 S1 115.76(15) . . ?
N6 C19 C20 110.4(2) . . ?
N6 C19 H19A 109.6 . . ?
C20 C19 H19A 109.6 . . ?
N6 C19 H19B 109.6 . . ?
C20 C19 H19B 109.6 . . ?
H19A C19 H19B 108.1 . . ?
C19 C20 H20A 109.5 . . ?
C19 C20 H20B 109.5 . . ?
H20A C20 H20B 109.5 . . ?
C19 C20 H20C 109.5 . . ?
H20A C20 H20C 109.5 . . ?
H20B C20 H20C 109.5 . . ?
C1 N1 C5 118.68(17) . . ?
C1 N1 Zn1 125.24(14) . . ?
C5 N1 Zn1 116.03(12) . . ?
C10 N2 C6 119.03(16) . . ?
C10 N2 Zn1 125.51(13) . . ?
C6 N2 Zn1 115.40(12) . . ?
C17 N3 N4 116.35(15) . . ?
C17 N3 Zn1 125.73(12) . . ?
N4 N3 Zn1 117.78(10) . . ?
C18 N4 N3 112.48(15) . . ?
O2 N5 O3 123.3(2) . . ?
O2 N5 C14 118.3(2) . . ?
O3 N5 C14 118.4(2) . . ?
C18 N6 C19 123.81(19) . . ?
C18 N6 H6A 119.4(18) . . ?
C19 N6 H6A 116.7(18) . . ?
C11 O1 Zn1 127.37(12) . . ?
C18 S1 Zn1 92.97(7) . . ?
O1 Zn1 N3 87.81(5) . . ?
O1 Zn1 N1 90.87(6) . . ?
N3 Zn1 N1 172.94(6) . . ?
O1 Zn1 N2 110.75(6) . . ?
N3 Zn1 N2 96.80(6) . . ?
N1 Zn1 N2 77.19(6) . . ?
O1 Zn1 S1 133.79(5) . . ?
N3 Zn1 S1 81.75(4) . . ?
N1 Zn1 S1 104.06(4) . . ?
N2 Zn1 S1 115.12(4) . . ?

_diffrn_measured_fraction_theta_max 0.994
_diffrn_reflns_theta_full        30.33
_diffrn_measured_fraction_theta_full 0.994
_refine_diff_density_max         0.535
_refine_diff_density_min         -0.319
_refine_diff_density_rms         0.054
####################################################################### 
# 
# 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 1427484'
_audit_update_record             
;
2016-02-01 deposited with the CCDC.
2016-02-17 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C22 H18 N6 O3 S Zn, C2 H3 N'
_chemical_formula_sum            'C24 H21 N7 O3 S Zn'
_chemical_formula_weight         552.94

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'
S S 0.1246 0.1234 '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                   7.9317(14)
_cell_length_b                   11.671(2)
_cell_length_c                   14.471(3)
_cell_angle_alpha                111.165(9)
_cell_angle_beta                 91.581(10)
_cell_angle_gamma                102.581(9)
_cell_volume                     1210.9(4)
_cell_formula_units_Z            2
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    4352
_cell_measurement_theta_min      2.65
_cell_measurement_theta_max      25.43

_exptl_crystal_description       Prism
_exptl_crystal_colour            Colorless
_exptl_crystal_size_max          0.11
_exptl_crystal_size_mid          0.09
_exptl_crystal_size_min          0.07
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.516
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             568
_exptl_absorpt_coefficient_mu    1.142
_exptl_absorpt_correction_type   Multi-scan
_exptl_absorpt_correction_T_min  0.6007
_exptl_absorpt_correction_T_max  0.7453
_exptl_absorpt_process_details   
'SADABS-2014/2 - Bruker AXS area detector scaling and absorption correction'

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            15934
_diffrn_reflns_av_R_equivalents  0.0693
_diffrn_reflns_av_sigmaI/netI    0.0804
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_theta_min         1.52
_diffrn_reflns_theta_max         26.18
_reflns_number_total             4562
_reflns_number_gt                3520
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'Sir-92 (Altomare et al., 1993)'
_computing_structure_refinement  'SHELXL-2014 (Sheldrick 2014)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'


_refine_special_details          
; 
 Refinement of F² against ALL reflections.  The weighted R-factor wR and 
 goodness of fit S are based on F², conventional R-factors R are based 
 on F, with F set to zero for negative F². The threshold expression of 
 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is 
 not relevant to the choice of reflections for refinement.  R-factors based 
 on F² are statistically about twice as large as those based on F, and R- 
 factors based on ALL data will be even larger. 
;

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0570P)²+19.2839P] 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         4562
_refine_ls_number_parameters     330
_refine_ls_number_restraints     3
_refine_ls_R_factor_all          0.1074
_refine_ls_R_factor_gt           0.0875
_refine_ls_wR_factor_ref         0.2389
_refine_ls_wR_factor_gt          0.2298
_refine_ls_goodness_of_fit_ref   1.102
_refine_ls_restrained_S_all      1.102
_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
C1 C 0.4321(10) 0.6571(8) 0.4326(7) 0.0265(19) Uani 1 1 d . . .
H1 H 0.3867 0.5861 0.4499 0.032 Uiso 1 1 calc R . .
C2 C 0.3670(11) 0.6568(8) 0.3414(7) 0.029(2) Uani 1 1 d . . .
H2 H 0.2795 0.5870 0.2978 0.035 Uiso 1 1 calc R . .
C3 C 0.4317(10) 0.7588(8) 0.3163(7) 0.0254(19) Uani 1 1 d . . .
H3 H 0.3904 0.7598 0.2544 0.030 Uiso 1 1 calc R . .
C4 C 0.5582(10) 0.8612(8) 0.3817(6) 0.0211(17) Uani 1 1 d . . .
C5 C 0.6183(10) 0.8532(7) 0.4710(6) 0.0160(16) Uani 1 1 d . . .
C6 C 0.7481(10) 0.9573(7) 0.5421(6) 0.0186(16) Uani 1 1 d . . .
C7 C 0.9233(11) 1.0403(8) 0.6925(6) 0.0220(17) Uani 1 1 d . . .
H7 H 0.9627 1.0322 0.7519 0.026 Uiso 1 1 calc R . .
C8 C 0.9964(11) 1.1514(7) 0.6767(6) 0.0231(18) Uani 1 1 d . . .
H8 H 1.0828 1.2171 0.7249 0.028 Uiso 1 1 calc R . .
C9 C 0.9427(11) 1.1644(8) 0.5920(6) 0.0229(18) Uani 1 1 d . . .
H9 H 0.9910 1.2396 0.5807 0.027 Uiso 1 1 calc R . .
C10 C 0.8141(10) 1.0653(7) 0.5203(6) 0.0174(16) Uani 1 1 d . . .
C11 C 0.7487(10) 1.0724(8) 0.4303(6) 0.0226(18) Uani 1 1 d . . .
H11 H 0.7907 1.1467 0.4167 0.027 Uiso 1 1 calc R . .
C12 C 0.6272(10) 0.9743(8) 0.3638(6) 0.0200(17) Uani 1 1 d . . .
H12 H 0.5869 0.9808 0.3039 0.024 Uiso 1 1 calc R . .
C13 C 0.4191(10) 0.8276(7) 0.7835(6) 0.0194(17) Uani 1 1 d . . .
C14 C 0.2670(10) 0.8731(8) 0.8094(6) 0.0218(17) Uani 1 1 d . . .
H14 H 0.2027 0.8891 0.7610 0.026 Uiso 1 1 calc R . .
C15 C 0.2106(11) 0.8945(8) 0.9003(6) 0.0259(19) Uani 1 1 d . . .
H15 H 0.1082 0.9241 0.9148 0.031 Uiso 1 1 calc R . .
C16 C 0.3057(11) 0.8722(9) 0.9726(6) 0.0278(19) Uani 1 1 d . . .
C17 C 0.4544(12) 0.8281(8) 0.9525(6) 0.0262(19) Uani 1 1 d . . .
H17 H 0.5159 0.8123 1.0021 0.031 Uiso 1 1 calc R . .
C18 C 0.5141(10) 0.8068(8) 0.8588(6) 0.0222(17) Uani 1 1 d . . .
C19 C 0.6661(10) 0.7549(8) 0.8429(6) 0.0228(18) Uani 1 1 d . . .
H19 H 0.7178 0.7420 0.8972 0.027 Uiso 1 1 calc R . .
C20 C 0.9279(10) 0.6227(7) 0.6749(6) 0.0206(17) Uani 1 1 d . . .
C21 C 1.1239(11) 0.5354(8) 0.7507(7) 0.0261(19) Uani 1 1 d . . .
H21A H 1.0354 0.4722 0.7656 0.031 Uiso 1 1 calc R . .
H21B H 1.1540 0.6145 0.8109 0.031 Uiso 1 1 calc R . .
C22 C 1.2854(11) 0.4857(9) 0.7245(7) 0.031(2) Uani 1 1 d . . .
H22A H 1.2542 0.4055 0.6666 0.047 Uiso 1 1 calc R . .
H22B H 1.3342 0.4718 0.7814 0.047 Uiso 1 1 calc R . .
H22C H 1.3719 0.5477 0.7086 0.047 Uiso 1 1 calc R . .
C23 C 0.278(2) 0.323(2) 0.9187(11) 0.109(8) Uani 1 1 d D . .
H23A H 0.3977 0.3496 0.9057 0.164 Uiso 1 1 calc R . .
H23B H 0.2006 0.2861 0.8558 0.164 Uiso 1 1 calc R . .
H23C H 0.2709 0.2596 0.9490 0.164 Uiso 1 1 calc R . .
C24 C 0.224(7) 0.433(3) 0.9872(16) 0.37(4) Uani 1 1 d D . .
N1 N 0.5532(8) 0.7512(6) 0.4952(5) 0.0208(15) Uani 1 1 d . . .
N2 N 0.8015(8) 0.9459(6) 0.6281(5) 0.0177(14) Uani 1 1 d . . .
N3 N 0.2443(12) 0.8905(9) 1.0676(6) 0.045(2) Uani 1 1 d . . .
N4 N 0.7369(8) 0.7249(6) 0.7605(5) 0.0191(14) Uani 1 1 d . . .
N5 N 0.8677(9) 0.6623(6) 0.7603(5) 0.0227(15) Uani 1 1 d . . .
N6 N 1.0544(9) 0.5597(7) 0.6689(6) 0.0273(16) Uani 1 1 d D . .
H6 H 1.074(13) 0.519(8) 0.611(3) 0.033 Uiso 1 1 d D . .
N7 N 0.234(4) 0.535(2) 1.0506(16) 0.218(15) Uani 1 1 d D . .
O1 O 0.4617(7) 0.8057(6) 0.6953(4) 0.0259(13) Uani 1 1 d . . .
O2 O 0.1187(10) 0.9425(9) 1.0876(5) 0.055(2) Uani 1 1 d . . .
O3 O 0.3213(11) 0.8635(9) 1.1288(6) 0.058(2) Uani 1 1 d . . .
S1 S 0.8620(3) 0.63948(19) 0.56423(16) 0.0231(5) Uani 1 1 d . . .
Zn1 Zn 0.67680(12) 0.77149(9) 0.63749(7) 0.0189(3) Uani 1 1 d . . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
C1 N1 1.313(11) . ?
C1 C2 1.404(13) . ?
C1 H1 0.9500 . ?
C2 C3 1.366(12) . ?
C2 H2 0.9500 . ?
C3 C4 1.392(12) . ?
C3 H3 0.9500 . ?
C4 C5 1.407(11) . ?
C4 C12 1.431(11) . ?
C5 N1 1.361(10) . ?
C5 C6 1.445(11) . ?
C6 N2 1.364(10) . ?
C6 C10 1.404(10) . ?
C7 N2 1.327(11) . ?
C7 C8 1.401(11) . ?
C7 H7 0.9500 . ?
C8 C9 1.357(12) . ?
C8 H8 0.9500 . ?
C9 C10 1.420(11) . ?
C9 H9 0.9500 . ?
C10 C11 1.425(11) . ?
C11 C12 1.355(12) . ?
C11 H11 0.9500 . ?
C12 H12 0.9500 . ?
C13 O1 1.278(10) . ?
C13 C14 1.428(11) . ?
C13 C18 1.429(11) . ?
C14 C15 1.355(12) . ?
C14 H14 0.9500 . ?
C15 C16 1.404(12) . ?
C15 H15 0.9500 . ?
C16 C17 1.384(12) . ?
C16 N3 1.430(11) . ?
C17 C18 1.402(11) . ?
C17 H17 0.9500 . ?
C18 C19 1.451(11) . ?
C19 N4 1.296(10) . ?
C19 H19 0.9500 . ?
C20 N5 1.298(11) . ?
C20 N6 1.355(10) . ?
C20 S1 1.761(8) . ?
C21 N6 1.434(11) . ?
C21 C22 1.521(12) . ?
C21 H21A 0.9900 . ?
C21 H21B 0.9900 . ?
C22 H22A 0.9800 . ?
C22 H22B 0.9800 . ?
C22 H22C 0.9800 . ?
C23 C24 1.47(4) . ?
C23 H23A 0.9800 . ?
C23 H23B 0.9800 . ?
C23 H23C 0.9800 . ?
C24 N7 1.20(4) . ?
N1 Zn1 2.166(7) . ?
N2 Zn1 2.114(6) . ?
N3 O3 1.230(11) . ?
N3 O2 1.264(11) . ?
N4 N5 1.393(9) . ?
N4 Zn1 2.112(7) . ?
N6 H6 0.84(6) . ?
O1 Zn1 1.976(6) . ?
S1 Zn1 2.356(2) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
N1 C1 C2 122.8(8) . . ?
N1 C1 H1 118.6 . . ?
C2 C1 H1 118.6 . . ?
C3 C2 C1 118.8(8) . . ?
C3 C2 H2 120.6 . . ?
C1 C2 H2 120.6 . . ?
C2 C3 C4 119.9(8) . . ?
C2 C3 H3 120.0 . . ?
C4 C3 H3 120.0 . . ?
C3 C4 C5 117.7(7) . . ?
C3 C4 C12 123.8(8) . . ?
C5 C4 C12 118.5(8) . . ?
N1 C5 C4 121.9(7) . . ?
N1 C5 C6 117.9(7) . . ?
C4 C5 C6 120.1(7) . . ?
N2 C6 C10 122.8(7) . . ?
N2 C6 C5 118.1(7) . . ?
C10 C6 C5 119.1(7) . . ?
N2 C7 C8 122.8(8) . . ?
N2 C7 H7 118.6 . . ?
C8 C7 H7 118.6 . . ?
C9 C8 C7 119.5(8) . . ?
C9 C8 H8 120.3 . . ?
C7 C8 H8 120.3 . . ?
C8 C9 C10 119.7(7) . . ?
C8 C9 H9 120.1 . . ?
C10 C9 H9 120.1 . . ?
C6 C10 C9 117.0(7) . . ?
C6 C10 C11 119.8(7) . . ?
C9 C10 C11 123.2(7) . . ?
C12 C11 C10 120.8(7) . . ?
C12 C11 H11 119.6 . . ?
C10 C11 H11 119.6 . . ?
C11 C12 C4 121.6(8) . . ?
C11 C12 H12 119.2 . . ?
C4 C12 H12 119.2 . . ?
O1 C13 C14 119.4(7) . . ?
O1 C13 C18 123.6(7) . . ?
C14 C13 C18 117.0(7) . . ?
C15 C14 C13 122.7(8) . . ?
C15 C14 H14 118.6 . . ?
C13 C14 H14 118.6 . . ?
C14 C15 C16 119.0(8) . . ?
C14 C15 H15 120.5 . . ?
C16 C15 H15 120.5 . . ?
C17 C16 C15 121.3(8) . . ?
C17 C16 N3 119.1(8) . . ?
C15 C16 N3 119.5(8) . . ?
C16 C17 C18 119.9(8) . . ?
C16 C17 H17 120.1 . . ?
C18 C17 H17 120.1 . . ?
C17 C18 C13 120.0(7) . . ?
C17 C18 C19 116.0(7) . . ?
C13 C18 C19 123.8(7) . . ?
N4 C19 C18 125.2(7) . . ?
N4 C19 H19 117.4 . . ?
C18 C19 H19 117.4 . . ?
N5 C20 N6 116.9(8) . . ?
N5 C20 S1 127.5(6) . . ?
N6 C20 S1 115.7(6) . . ?
N6 C21 C22 109.9(7) . . ?
N6 C21 H21A 109.7 . . ?
C22 C21 H21A 109.7 . . ?
N6 C21 H21B 109.7 . . ?
C22 C21 H21B 109.7 . . ?
H21A C21 H21B 108.2 . . ?
C21 C22 H22A 109.5 . . ?
C21 C22 H22B 109.5 . . ?
H22A C22 H22B 109.5 . . ?
C21 C22 H22C 109.5 . . ?
H22A C22 H22C 109.5 . . ?
H22B C22 H22C 109.5 . . ?
C24 C23 H23A 109.5 . . ?
C24 C23 H23B 109.5 . . ?
H23A C23 H23B 109.5 . . ?
C24 C23 H23C 109.5 . . ?
H23A C23 H23C 109.5 . . ?
H23B C23 H23C 109.5 . . ?
N7 C24 C23 160(6) . . ?
C1 N1 C5 118.8(7) . . ?
C1 N1 Zn1 129.5(6) . . ?
C5 N1 Zn1 111.7(5) . . ?
C7 N2 C6 118.2(7) . . ?
C7 N2 Zn1 128.7(5) . . ?
C6 N2 Zn1 113.2(5) . . ?
O3 N3 O2 122.5(8) . . ?
O3 N3 C16 119.6(8) . . ?
O2 N3 C16 117.7(8) . . ?
C19 N4 N5 113.9(7) . . ?
C19 N4 Zn1 125.3(5) . . ?
N5 N4 Zn1 120.7(5) . . ?
C20 N5 N4 113.7(7) . . ?
C20 N6 C21 123.9(8) . . ?
C20 N6 H6 116(7) . . ?
C21 N6 H6 119(7) . . ?
C13 O1 Zn1 131.6(5) . . ?
C20 S1 Zn1 95.2(3) . . ?
O1 Zn1 N4 87.3(2) . . ?
O1 Zn1 N2 103.0(2) . . ?
N4 Zn1 N2 121.8(3) . . ?
O1 Zn1 N1 88.0(2) . . ?
N4 Zn1 N1 159.1(2) . . ?
N2 Zn1 N1 79.1(2) . . ?
O1 Zn1 S1 153.77(19) . . ?
N4 Zn1 S1 81.82(19) . . ?
N2 Zn1 S1 103.01(18) . . ?
N1 Zn1 S1 93.67(19) . . ?

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
N1 C1 C2 C3 -0.1(14) . . . . ?
C1 C2 C3 C4 -0.9(13) . . . . ?
C2 C3 C4 C5 1.8(12) . . . . ?
C2 C3 C4 C12 -176.9(8) . . . . ?
C3 C4 C5 N1 -1.8(11) . . . . ?
C12 C4 C5 N1 177.0(7) . . . . ?
C3 C4 C5 C6 -179.3(7) . . . . ?
C12 C4 C5 C6 -0.5(11) . . . . ?
N1 C5 C6 N2 1.8(10) . . . . ?
C4 C5 C6 N2 179.4(7) . . . . ?
N1 C5 C6 C10 -178.3(7) . . . . ?
C4 C5 C6 C10 -0.6(11) . . . . ?
N2 C7 C8 C9 -0.4(12) . . . . ?
C7 C8 C9 C10 -0.3(12) . . . . ?
N2 C6 C10 C9 0.6(11) . . . . ?
C5 C6 C10 C9 -179.4(7) . . . . ?
N2 C6 C10 C11 -178.1(7) . . . . ?
C5 C6 C10 C11 1.9(11) . . . . ?
C8 C9 C10 C6 0.3(11) . . . . ?
C8 C9 C10 C11 178.9(8) . . . . ?
C6 C10 C11 C12 -2.1(12) . . . . ?
C9 C10 C11 C12 179.3(8) . . . . ?
C10 C11 C12 C4 0.9(12) . . . . ?
C3 C4 C12 C11 179.1(8) . . . . ?
C5 C4 C12 C11 0.4(12) . . . . ?
O1 C13 C14 C15 177.8(8) . . . . ?
C18 C13 C14 C15 -1.1(12) . . . . ?
C13 C14 C15 C16 0.6(13) . . . . ?
C14 C15 C16 C17 -0.5(14) . . . . ?
C14 C15 C16 N3 -178.0(8) . . . . ?
C15 C16 C17 C18 1.1(14) . . . . ?
N3 C16 C17 C18 178.5(8) . . . . ?
C16 C17 C18 C13 -1.6(13) . . . . ?
C16 C17 C18 C19 -177.2(8) . . . . ?
O1 C13 C18 C17 -177.3(8) . . . . ?
C14 C13 C18 C17 1.6(12) . . . . ?
O1 C13 C18 C19 -2.0(13) . . . . ?
C14 C13 C18 C19 176.8(8) . . . . ?
C17 C18 C19 N4 177.6(8) . . . . ?
C13 C18 C19 N4 2.1(13) . . . . ?
C2 C1 N1 C5 0.2(12) . . . . ?
C2 C1 N1 Zn1 -178.7(6) . . . . ?
C4 C5 N1 C1 0.7(11) . . . . ?
C6 C5 N1 C1 178.4(7) . . . . ?
C4 C5 N1 Zn1 179.8(6) . . . . ?
C6 C5 N1 Zn1 -2.5(8) . . . . ?
C8 C7 N2 C6 1.2(11) . . . . ?
C8 C7 N2 Zn1 179.6(6) . . . . ?
C10 C6 N2 C7 -1.3(11) . . . . ?
C5 C6 N2 C7 178.6(7) . . . . ?
C10 C6 N2 Zn1 -179.9(6) . . . . ?
C5 C6 N2 Zn1 0.1(8) . . . . ?
C17 C16 N3 O3 -2.0(15) . . . . ?
C15 C16 N3 O3 175.5(10) . . . . ?
C17 C16 N3 O2 173.2(9) . . . . ?
C15 C16 N3 O2 -9.3(15) . . . . ?
C18 C19 N4 N5 -172.3(7) . . . . ?
C18 C19 N4 Zn1 10.9(12) . . . . ?
N6 C20 N5 N4 -179.3(7) . . . . ?
S1 C20 N5 N4 -0.2(10) . . . . ?
C19 N4 N5 C20 174.4(7) . . . . ?
Zn1 N4 N5 C20 -8.6(9) . . . . ?
N5 C20 N6 C21 -0.2(12) . . . . ?
S1 C20 N6 C21 -179.4(6) . . . . ?
C22 C21 N6 C20 -169.2(8) . . . . ?
C14 C13 O1 Zn1 168.1(6) . . . . ?
C18 C13 O1 Zn1 -13.1(12) . . . . ?
N5 C20 S1 Zn1 7.0(7) . . . . ?
N6 C20 S1 Zn1 -173.9(6) . . . . ?
C13 O1 Zn1 N4 18.8(7) . . . . ?
C13 O1 Zn1 N2 -103.2(7) . . . . ?
C13 O1 Zn1 N1 178.5(7) . . . . ?
C13 O1 Zn1 S1 84.2(8) . . . . ?
C19 N4 Zn1 O1 -17.0(7) . . . . ?
N5 N4 Zn1 O1 166.3(6) . . . . ?
C19 N4 Zn1 N2 86.6(7) . . . . ?
N5 N4 Zn1 N2 -90.0(6) . . . . ?
C19 N4 Zn1 N1 -94.4(9) . . . . ?
N5 N4 Zn1 N1 89.0(9) . . . . ?
C19 N4 Zn1 S1 -173.1(7) . . . . ?
N5 N4 Zn1 S1 10.3(5) . . . . ?
C7 N2 Zn1 O1 95.2(7) . . . . ?
C6 N2 Zn1 O1 -86.4(5) . . . . ?
C7 N2 Zn1 N4 0.2(8) . . . . ?
C6 N2 Zn1 N4 178.6(5) . . . . ?
C7 N2 Zn1 N1 -179.4(7) . . . . ?
C6 N2 Zn1 N1 -1.1(5) . . . . ?
C7 N2 Zn1 S1 -88.2(7) . . . . ?
C6 N2 Zn1 S1 90.2(5) . . . . ?
C1 N1 Zn1 O1 -75.4(7) . . . . ?
C5 N1 Zn1 O1 105.6(5) . . . . ?
C1 N1 Zn1 N4 1.8(12) . . . . ?
C5 N1 Zn1 N4 -177.2(6) . . . . ?
C1 N1 Zn1 N2 -179.1(8) . . . . ?
C5 N1 Zn1 N2 1.9(5) . . . . ?
C1 N1 Zn1 S1 78.4(7) . . . . ?
C5 N1 Zn1 S1 -100.6(5) . . . . ?
C20 S1 Zn1 O1 -73.8(5) . . . . ?
C20 S1 Zn1 N4 -7.4(3) . . . . ?
C20 S1 Zn1 N2 113.5(3) . . . . ?
C20 S1 Zn1 N1 -166.8(3) . . . . ?

_diffrn_measured_fraction_theta_max 0.940
_diffrn_reflns_theta_full        26.18
_diffrn_measured_fraction_theta_full 0.940
_refine_diff_density_max         2.169
_refine_diff_density_min         -0.735
_refine_diff_density_rms         0.161

# start Validation Reply Form
_vrf_PLAT214_shelxl              
;
RESPONSE: This Alert is due to the presence of unresolved disorder 
in the solvent molecule present in
lattice of crystal system and thermal parametrs of their atoms are high.
;
_vrf_PLAT413_shelxl              
;
RESPONSE: This Alert is due to the presence of unresolved disorder 
in crystal system and thermal parametrs are high.
;
# end Validation Reply Form 

####################################################################### 
# 
# 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 1427485'
_audit_update_record             
;
2016-02-01 deposited with the CCDC.
2016-02-17 downloaded from the CCDC.
;
_audit_creation_date             2015-09-24
_audit_creation_method           
;
Olex2 1.2
(compiled 2015.01.26 svn.r3150 for OlexSys, GUI svn.r4998)
;
_shelxl_version_number           2014/6
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C24 H18 N6 O3 S Zn'
_chemical_formula_sum            'C24 H18 N6 O3 S Zn'
_chemical_formula_weight         535.87
_chemical_melting_point          ?
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'
S S 0.3331 0.5567 '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'

_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.
;
_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_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   9.7377(13)
_cell_length_b                   10.8604(12)
_cell_length_c                   11.9599(15)
_cell_angle_alpha                67.510(11)
_cell_angle_beta                 76.142(11)
_cell_angle_gamma                76.077(11)
_cell_volume                     1118.9(3)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    3757
_cell_measurement_temperature    173(2)
_cell_measurement_theta_max      71.2453
_cell_measurement_theta_min      4.0524
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    2.749
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.71740
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro, Agilent Technologies,
Version 1.171.35.19 (release 27-10-2011 CrysAlis171 .NET)
(compiled Oct 27 2011,15:02:11)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            brown
_exptl_crystal_colour_primary    brown
_exptl_crystal_density_diffrn    1.591
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       prism
_exptl_crystal_F_000             548
_exptl_crystal_size_max          0.32
_exptl_crystal_size_mid          0.24
_exptl_crystal_size_min          0.18
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0350
_diffrn_reflns_av_unetI/netI     0.0427
_diffrn_reflns_Laue_measured_fraction_full 0.991
_diffrn_reflns_Laue_measured_fraction_max 0.968
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            6935
_diffrn_reflns_point_group_measured_fraction_full 0.991
_diffrn_reflns_point_group_measured_fraction_max 0.968
_diffrn_reflns_theta_full        67.500
_diffrn_reflns_theta_max         71.379
_diffrn_reflns_theta_min         4.056
_diffrn_ambient_temperature      173(2)
_diffrn_detector_area_resol_mean 16.1500
_diffrn_measured_fraction_theta_full 0.991
_diffrn_measured_fraction_theta_max 0.968
_diffrn_measurement_device_type  'Agilent, Eos, Gemini'
_diffrn_measurement_method       'ω scans'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_source                   'Enhance (Cu) X-ray Source'
_diffrn_special_details          ?
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                3884
_reflns_number_total             4215
_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.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'CrysAlisPro, Agilent, 2014'
_computing_data_collection       'CrysAlisPro, Agilent, 2014'
_computing_data_reduction        'CrysAlisRed, Agilent, 2014'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2008)'
_computing_structure_solution    
;
Superflip (Palatinus & Chapuis, 2007;Palatinus & van der Lee, 2008;
Palatinus et al., 2012)
;
_refine_diff_density_max         0.555
_refine_diff_density_min         -0.476
_refine_diff_density_rms         0.075
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.054
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     316
_refine_ls_number_reflns         4215
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0416
_refine_ls_R_factor_gt           0.0388
_refine_ls_restrained_S_all      1.054
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0664P)²+0.1334P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1045
_refine_ls_wR_factor_ref         0.1078
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All N(H) groups
2.a Aromatic/amide H refined with riding coordinates:
 N3(H3), C1(H1), C2(H2), C3(H3A), C4(H4), C7(H7), C8(H8), C9(H9), C10(H10),
 C12(H12), C13(H13), C15(H15), C17(H17), C20(H20), C21(H21), C22(H22), C23(H23),
  C24(H24)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   ?
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 0.77952(3) 0.25382(3) 0.20513(2) 0.02528(12) Uani 1 1 d . . . . .
S1 S 0.91577(6) 0.13375(5) 0.08030(5) 0.02942(14) Uani 1 1 d . . . . .
O1 O 0.58345(16) 0.27425(16) 0.29660(14) 0.0312(3) Uani 1 1 d . . . . .
O2 O 0.2766(2) 0.1228(2) 0.83958(18) 0.0479(5) Uani 1 1 d . . . . .
O3 O 0.4544(2) -0.0420(2) 0.85874(18) 0.0583(6) Uani 1 1 d . . . . .
N1 N 0.75286(19) 0.45011(18) 0.06878(16) 0.0266(4) Uani 1 1 d . . . . .
N2 N 0.89932(18) 0.36138(18) 0.25203(16) 0.0250(4) Uani 1 1 d . . . . .
N3 N 1.1279(2) -0.05738(19) 0.15982(17) 0.0307(4) Uani 1 1 d . . . . .
H3 H 1.1543 -0.0285 0.0796 0.037 Uiso 1 1 calc R . . . .
N4 N 0.95549(19) -0.01624(18) 0.31863(17) 0.0285(4) Uani 1 1 d . . . . .
N5 N 0.82872(19) 0.06818(17) 0.34272(17) 0.0257(4) Uani 1 1 d . . . . .
N6 N 0.3854(2) 0.0612(2) 0.79605(19) 0.0376(5) Uani 1 1 d . . . . .
C1 C 0.6796(2) 0.4879(3) -0.0246(2) 0.0352(5) Uani 1 1 d . . . . .
H1 H 0.6385 0.4221 -0.0338 0.042 Uiso 1 1 calc R . . . .
C2 C 0.6617(3) 0.6182(3) -0.1077(2) 0.0433(6) Uani 1 1 d . . . . .
H2 H 0.6086 0.6421 -0.1722 0.052 Uiso 1 1 calc R . . . .
C3 C 0.7232(3) 0.7125(3) -0.0942(2) 0.0430(6) Uani 1 1 d . . . . .
H3A H 0.7123 0.8031 -0.1495 0.052 Uiso 1 1 calc R . . . .
C4 C 0.8003(3) 0.6752(2) -0.0005(2) 0.0369(5) Uani 1 1 d . . . . .
H4 H 0.8438 0.7393 0.0091 0.044 Uiso 1 1 calc R . . . .
C5 C 0.8136(2) 0.5426(2) 0.0799(2) 0.0266(4) Uani 1 1 d . . . . .
C6 C 0.8955(2) 0.4933(2) 0.1835(2) 0.0261(4) Uani 1 1 d . . . . .
C7 C 0.9656(3) 0.5751(3) 0.2076(2) 0.0381(5) Uani 1 1 d . . . . .
H7 H 0.9628 0.6677 0.1578 0.046 Uiso 1 1 calc R . . . .
C8 C 1.0400(3) 0.5194(3) 0.3060(3) 0.0437(6) Uani 1 1 d . . . . .
H8 H 1.0881 0.5737 0.3248 0.052 Uiso 1 1 calc R . . . .
C9 C 1.0434(3) 0.3847(3) 0.3761(2) 0.0385(5) Uani 1 1 d . . . . .
H9 H 1.0934 0.3447 0.4439 0.046 Uiso 1 1 calc R . . . .
C10 C 0.9726(2) 0.3086(2) 0.3459(2) 0.0316(5) Uani 1 1 d . . . . .
H10 H 0.9761 0.2154 0.3935 0.038 Uiso 1 1 calc R . . . .
C11 C 0.5411(2) 0.2175(2) 0.4132(2) 0.0264(4) Uani 1 1 d . . . . .
C12 C 0.4054(2) 0.2714(2) 0.4671(2) 0.0309(5) Uani 1 1 d . . . . .
H12 H 0.3477 0.3444 0.4155 0.037 Uiso 1 1 calc R . . . .
C13 C 0.3538(2) 0.2229(2) 0.5902(2) 0.0322(5) Uani 1 1 d . . . . .
H13 H 0.2641 0.2637 0.6237 0.039 Uiso 1 1 calc R . . . .
C14 C 0.4359(2) 0.1123(2) 0.6653(2) 0.0295(5) Uani 1 1 d . . . . .
C15 C 0.5658(2) 0.0526(2) 0.6172(2) 0.0280(4) Uani 1 1 d . . . . .
H15 H 0.6184 -0.0243 0.6699 0.034 Uiso 1 1 calc R . . . .
C16 C 0.6218(2) 0.1023(2) 0.4928(2) 0.0256(4) Uani 1 1 d . . . . .
C17 C 0.7576(2) 0.0296(2) 0.4519(2) 0.0265(4) Uani 1 1 d . . . . .
H17 H 0.7968 -0.0519 0.5097 0.032 Uiso 1 1 calc R . . . .
C18 C 1.0014(2) 0.0123(2) 0.2002(2) 0.0264(4) Uani 1 1 d . . . . .
C19 C 1.2232(2) -0.1670(2) 0.2238(2) 0.0269(4) Uani 1 1 d . . . . .
C20 C 1.2036(2) -0.2299(2) 0.3503(2) 0.0294(4) Uani 1 1 d . . . . .
H20 H 1.1220 -0.1986 0.4003 0.035 Uiso 1 1 calc R . . . .
C21 C 1.3049(2) -0.3398(2) 0.4036(2) 0.0332(5) Uani 1 1 d . . . . .
H21 H 1.2910 -0.3831 0.4902 0.040 Uiso 1 1 calc R . . . .
C22 C 1.4236(3) -0.3861(2) 0.3334(2) 0.0358(5) Uani 1 1 d . . . . .
H22 H 1.4917 -0.4607 0.3708 0.043 Uiso 1 1 calc R . . . .
C23 C 1.4434(3) -0.3228(3) 0.2067(2) 0.0404(6) Uani 1 1 d . . . . .
H23 H 1.5256 -0.3542 0.1573 0.048 Uiso 1 1 calc R . . . .
C24 C 1.3441(3) -0.2141(3) 0.1523(2) 0.0372(5) Uani 1 1 d . . . . .
H24 H 1.3585 -0.1714 0.0657 0.045 Uiso 1 1 calc R . . . .


_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 S1 2.3233(7) . ?
Zn1 O1 1.9679(16) . ?
Zn1 N1 2.1326(18) . ?
Zn1 N2 2.1238(18) . ?
Zn1 N5 2.0920(18) . ?
S1 C18 1.757(2) . ?
O1 C11 1.297(3) . ?
O2 N6 1.226(3) . ?
O3 N6 1.227(3) . ?
N1 C1 1.347(3) . ?
N1 C5 1.342(3) . ?
N2 C6 1.347(3) . ?
N2 C10 1.339(3) . ?
N3 H3 0.8800 . ?
N3 C18 1.367(3) . ?
N3 C19 1.406(3) . ?
N4 N5 1.391(2) . ?
N4 C18 1.315(3) . ?
N5 C17 1.284(3) . ?
N6 C14 1.447(3) . ?
C1 H1 0.9500 . ?
C1 C2 1.382(4) . ?
C2 H2 0.9500 . ?
C2 C3 1.379(4) . ?
C3 H3A 0.9500 . ?
C3 C4 1.377(4) . ?
C4 H4 0.9500 . ?
C4 C5 1.388(3) . ?
C5 C6 1.489(3) . ?
C6 C7 1.387(3) . ?
C7 H7 0.9500 . ?
C7 C8 1.389(4) . ?
C8 H8 0.9500 . ?
C8 C9 1.377(4) . ?
C9 H9 0.9500 . ?
C9 C10 1.381(3) . ?
C10 H10 0.9500 . ?
C11 C12 1.419(3) . ?
C11 C16 1.437(3) . ?
C12 H12 0.9500 . ?
C12 C13 1.371(3) . ?
C13 H13 0.9500 . ?
C13 C14 1.395(3) . ?
C14 C15 1.376(3) . ?
C15 H15 0.9500 . ?
C15 C16 1.393(3) . ?
C16 C17 1.447(3) . ?
C17 H17 0.9500 . ?
C19 C20 1.388(3) . ?
C19 C24 1.393(3) . ?
C20 H20 0.9500 . ?
C20 C21 1.399(3) . ?
C21 H21 0.9500 . ?
C21 C22 1.368(3) . ?
C22 H22 0.9500 . ?
C22 C23 1.390(4) . ?
C23 H23 0.9500 . ?
C23 C24 1.384(3) . ?
C24 H24 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 S1 138.57(5) . . ?
O1 Zn1 N1 95.16(7) . . ?
O1 Zn1 N2 107.31(7) . . ?
O1 Zn1 N5 89.18(7) . . ?
N1 Zn1 S1 98.79(5) . . ?
N2 Zn1 S1 113.81(5) . . ?
N2 Zn1 N1 76.77(7) . . ?
N5 Zn1 S1 81.77(5) . . ?
N5 Zn1 N1 172.56(7) . . ?
N5 Zn1 N2 96.17(7) . . ?
C18 S1 Zn1 92.77(7) . . ?
C11 O1 Zn1 127.41(13) . . ?
C1 N1 Zn1 125.59(16) . . ?
C5 N1 Zn1 115.96(14) . . ?
C5 N1 C1 118.45(19) . . ?
C6 N2 Zn1 116.32(14) . . ?
C10 N2 Zn1 124.74(15) . . ?
C10 N2 C6 118.90(19) . . ?
C18 N3 H3 114.3 . . ?
C18 N3 C19 131.36(19) . . ?
C19 N3 H3 114.3 . . ?
C18 N4 N5 111.89(17) . . ?
N4 N5 Zn1 117.86(14) . . ?
C17 N5 Zn1 125.39(15) . . ?
C17 N5 N4 116.49(18) . . ?
O2 N6 O3 122.8(2) . . ?
O2 N6 C14 118.9(2) . . ?
O3 N6 C14 118.3(2) . . ?
N1 C1 H1 118.5 . . ?
N1 C1 C2 122.9(2) . . ?
C2 C1 H1 118.5 . . ?
C1 C2 H2 121.0 . . ?
C3 C2 C1 117.9(2) . . ?
C3 C2 H2 121.0 . . ?
C2 C3 H3A 120.0 . . ?
C4 C3 C2 119.9(2) . . ?
C4 C3 H3A 120.0 . . ?
C3 C4 H4 120.5 . . ?
C3 C4 C5 119.0(2) . . ?
C5 C4 H4 120.5 . . ?
N1 C5 C4 121.7(2) . . ?
N1 C5 C6 115.66(18) . . ?
C4 C5 C6 122.7(2) . . ?
N2 C6 C5 115.17(18) . . ?
N2 C6 C7 121.7(2) . . ?
C7 C6 C5 123.1(2) . . ?
C6 C7 H7 120.6 . . ?
C6 C7 C8 118.8(2) . . ?
C8 C7 H7 120.6 . . ?
C7 C8 H8 120.3 . . ?
C9 C8 C7 119.3(2) . . ?
C9 C8 H8 120.3 . . ?
C8 C9 H9 120.6 . . ?
C8 C9 C10 118.8(2) . . ?
C10 C9 H9 120.6 . . ?
N2 C10 C9 122.5(2) . . ?
N2 C10 H10 118.8 . . ?
C9 C10 H10 118.8 . . ?
O1 C11 C12 118.42(19) . . ?
O1 C11 C16 124.64(19) . . ?
C12 C11 C16 116.9(2) . . ?
C11 C12 H12 118.5 . . ?
C13 C12 C11 123.0(2) . . ?
C13 C12 H12 118.5 . . ?
C12 C13 H13 120.7 . . ?
C12 C13 C14 118.6(2) . . ?
C14 C13 H13 120.7 . . ?
C13 C14 N6 119.6(2) . . ?
C15 C14 N6 119.5(2) . . ?
C15 C14 C13 120.9(2) . . ?
C14 C15 H15 119.3 . . ?
C14 C15 C16 121.5(2) . . ?
C16 C15 H15 119.3 . . ?
C11 C16 C17 124.2(2) . . ?
C15 C16 C11 119.07(19) . . ?
C15 C16 C17 116.65(19) . . ?
N5 C17 C16 124.28(19) . . ?
N5 C17 H17 117.9 . . ?
C16 C17 H17 117.9 . . ?
N3 C18 S1 113.16(16) . . ?
N4 C18 S1 127.04(16) . . ?
N4 C18 N3 119.80(19) . . ?
C20 C19 N3 124.6(2) . . ?
C20 C19 C24 119.3(2) . . ?
C24 C19 N3 116.1(2) . . ?
C19 C20 H20 120.3 . . ?
C19 C20 C21 119.5(2) . . ?
C21 C20 H20 120.3 . . ?
C20 C21 H21 119.4 . . ?
C22 C21 C20 121.2(2) . . ?
C22 C21 H21 119.4 . . ?
C21 C22 H22 120.4 . . ?
C21 C22 C23 119.3(2) . . ?
C23 C22 H22 120.4 . . ?
C22 C23 H23 119.8 . . ?
C24 C23 C22 120.3(2) . . ?
C24 C23 H23 119.8 . . ?
C19 C24 H24 119.8 . . ?
C23 C24 C19 120.4(2) . . ?
C23 C24 H24 119.8 . . ?

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 H3 S1 0.88 2.85 3.419(2) 124.2 2_755
C2 H2 O1 0.95 2.45 3.374(3) 163.4 2_665
C4 H4 O2 0.95 2.67 3.290(3) 123.8 2_666
C7 H7 O2 0.95 2.84 3.485(3) 125.8 2_666
C20 H20 N4 0.95 2.29 2.904(3) 121.8 .
C24 H24 O3 0.95 2.42 3.334(3) 162.4 1_654

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 S1 C18 N3 -159.54(15) . . . . ?
Zn1 S1 C18 N4 21.3(2) . . . . ?
Zn1 O1 C11 C12 163.50(15) . . . . ?
Zn1 O1 C11 C16 -16.8(3) . . . . ?
Zn1 N1 C1 C2 177.58(18) . . . . ?
Zn1 N1 C5 C4 -177.91(17) . . . . ?
Zn1 N1 C5 C6 2.1(2) . . . . ?
Zn1 N2 C6 C5 -3.2(2) . . . . ?
Zn1 N2 C6 C7 177.92(18) . . . . ?
Zn1 N2 C10 C9 -176.87(17) . . . . ?
Zn1 N5 C17 C16 7.7(3) . . . . ?
O1 C11 C12 C13 -176.9(2) . . . . ?
O1 C11 C16 C15 178.6(2) . . . . ?
O1 C11 C16 C17 -3.7(3) . . . . ?
O2 N6 C14 C13 -5.6(3) . . . . ?
O2 N6 C14 C15 173.1(2) . . . . ?
O3 N6 C14 C13 174.9(2) . . . . ?
O3 N6 C14 C15 -6.4(3) . . . . ?
N1 C1 C2 C3 0.7(4) . . . . ?
N1 C5 C6 N2 0.7(3) . . . . ?
N1 C5 C6 C7 179.5(2) . . . . ?
N2 C6 C7 C8 -0.8(4) . . . . ?
N3 C19 C20 C21 179.0(2) . . . . ?
N3 C19 C24 C23 -179.2(2) . . . . ?
N4 N5 C17 C16 -178.26(19) . . . . ?
N5 N4 C18 S1 -3.4(3) . . . . ?
N5 N4 C18 N3 177.47(19) . . . . ?
N6 C14 C15 C16 -176.9(2) . . . . ?
C1 N1 C5 C4 1.2(3) . . . . ?
C1 N1 C5 C6 -178.74(19) . . . . ?
C1 C2 C3 C4 0.4(4) . . . . ?
C2 C3 C4 C5 -0.6(4) . . . . ?
C3 C4 C5 N1 -0.2(3) . . . . ?
C3 C4 C5 C6 179.7(2) . . . . ?
C4 C5 C6 N2 -179.2(2) . . . . ?
C4 C5 C6 C7 -0.4(3) . . . . ?
C5 N1 C1 C2 -1.4(3) . . . . ?
C5 C6 C7 C8 -179.6(2) . . . . ?
C6 N2 C10 C9 0.7(3) . . . . ?
C6 C7 C8 C9 0.6(4) . . . . ?
C7 C8 C9 C10 0.2(4) . . . . ?
C8 C9 C10 N2 -0.9(4) . . . . ?
C10 N2 C6 C5 179.02(18) . . . . ?
C10 N2 C6 C7 0.2(3) . . . . ?
C11 C12 C13 C14 -2.5(3) . . . . ?
C11 C16 C17 N5 7.8(3) . . . . ?
C12 C11 C16 C15 -1.8(3) . . . . ?
C12 C11 C16 C17 176.0(2) . . . . ?
C12 C13 C14 N6 178.6(2) . . . . ?
C12 C13 C14 C15 -0.2(3) . . . . ?
C13 C14 C15 C16 1.8(3) . . . . ?
C14 C15 C16 C11 -0.7(3) . . . . ?
C14 C15 C16 C17 -178.7(2) . . . . ?
C15 C16 C17 N5 -174.4(2) . . . . ?
C16 C11 C12 C13 3.5(3) . . . . ?
C18 N3 C19 C20 0.5(4) . . . . ?
C18 N3 C19 C24 179.8(2) . . . . ?
C18 N4 N5 Zn1 -21.4(2) . . . . ?
C18 N4 N5 C17 164.1(2) . . . . ?
C19 N3 C18 S1 -175.12(19) . . . . ?
C19 N3 C18 N4 4.1(4) . . . . ?
C19 C20 C21 C22 0.4(4) . . . . ?
C20 C19 C24 C23 0.2(4) . . . . ?
C20 C21 C22 C23 -0.1(4) . . . . ?
C21 C22 C23 C24 -0.1(4) . . . . ?
C22 C23 C24 C19 0.0(4) . . . . ?
C24 C19 C20 C21 -0.4(3) . . . . ?

