# Electronic Supplementary Material (ESI) for RSC Advances.
# This journal is © The Royal Society of Chemistry 2015

####################################################################### 
# 
# 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_shelx
_database_code_depnum_ccdc_archive 'CCDC 1411214'

_audit_update_record             
;
2015-07-07 deposited with the CCDC.
2015-12-14 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/6
_chemical_name_systematic        UZAR-S12
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C21 H24 N14 O5 S3 Zn2, C3 H7 N O'
_chemical_formula_sum            'C24 H31 N15 O6 S3 Zn2'
_chemical_formula_weight         852.56

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'

_space_group_crystal_system      monoclinic
_space_group_IT_number           7
_space_group_name_H-M_alt        'P n'
_space_group_name_Hall           'P -2yac'

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

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

_cell_length_a                   11.6765(4)
_cell_length_b                   10.3852(2)
_cell_length_c                   15.0913(4)
_cell_angle_alpha                90
_cell_angle_beta                 107.074(3)
_cell_angle_gamma                90
_cell_volume                     1749.36(9)
_cell_formula_units_Z            2
_cell_measurement_temperature    296(1)
_cell_measurement_reflns_used    4474
_cell_measurement_theta_min      3.4340
_cell_measurement_theta_max      23.5530


_exptl_crystal_description       block
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.619
_exptl_crystal_F_000             872
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.160
_exptl_crystal_size_mid          0.040
_exptl_crystal_size_min          0.030
_exptl_absorpt_coefficient_mu    1.612
_shelx_estimated_absorpt_T_min   0.782
_shelx_estimated_absorpt_T_max   0.953
_exptl_absorpt_correction_T_min  0.96735
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET)
(compiled Feb  1 2013,16:14:44)
Multi-scan absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      296(1)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'Enhance (Mo) X-ray Source'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Xcalibur, Sapphire3'
_diffrn_detector_area_resol_mean 16.3990
_diffrn_measurement_method       ω-scans
_diffrn_reflns_number            24135
_diffrn_reflns_av_unetI/netI     0.0668
_diffrn_reflns_av_R_equivalents  0.0632
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_theta_min         3.269
_diffrn_reflns_theta_max         24.998
_diffrn_reflns_theta_full        25.000
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measured_fraction_theta_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_point_group_measured_fraction_full 0.998
_reflns_number_total             6163
_reflns_number_gt                4837
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.996
_reflns_Friedel_fraction_max     0.998
_reflns_Friedel_fraction_full    0.998

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

_computing_data_collection       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET)
(compiled Feb  1 2013,16:14:44)
;
_computing_cell_refinement       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET)
(compiled Feb  1 2013,16:14:44)
;
_computing_data_reduction        
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET)
(compiled Feb  1 2013,16:14:44)
;
_computing_structure_solution    
; 
SIR92
A. Altomare, G. Cascarano, C. Giacovazzo and A. Guagliardi, J. Appl.
 Crystallogr., 1994, 27, 435.
;
_computing_structure_refinement  'SHELXL-2014/6 (Sheldrick, 2014)'
_computing_molecular_graphics    'Diamond 3.2i'
_computing_publication_material  'SHELXL-2014/6 (Sheldrick, 2014)'
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0351P)²+1.4400P] 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_abs_structure_details 
;
 Flack x determined using 1940 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.433(10)
_chemical_absolute_configuration ad
_refine_ls_number_reflns         6163
_refine_ls_number_parameters     459
_refine_ls_number_restraints     29
_refine_ls_R_factor_all          0.0727
_refine_ls_R_factor_gt           0.0519
_refine_ls_wR_factor_ref         0.1035
_refine_ls_wR_factor_gt          0.0956
_refine_ls_goodness_of_fit_ref   1.042
_refine_ls_restrained_S_all      1.048
_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_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 0.54923(8) 0.14328(11) 0.57653(6) 0.0316(4) Uani 1 1 d . . . . .
Zn2 Zn 0.13585(8) 0.35638(11) 0.27487(6) 0.0296(4) Uani 1 1 d . . . . .
N1 N 0.4649(7) 0.2469(7) 0.4620(5) 0.0330(19) Uani 1 1 d . . . . .
C1 C 0.3480(11) 0.2612(13) 0.4260(9) 0.029(2) Uani 1 1 d . . . . .
H1 H 0.2942 0.2342 0.4571 0.035 Uiso 1 1 calc R U . . .
N2 N 0.3112(6) 0.3168(7) 0.3420(5) 0.0329(18) Uani 1 1 d . . . . .
C2 C 0.4170(8) 0.3390(8) 0.3209(6) 0.029(2) Uani 1 1 d . . . . .
C3 C 0.4475(10) 0.4039(10) 0.2490(7) 0.041(3) Uani 1 1 d . . . . .
N3 N 0.5606(9) 0.4128(10) 0.2514(7) 0.050(3) Uani 1 1 d . . . . .
C4 C 0.6451(9) 0.3632(10) 0.3246(7) 0.049(3) Uani 1 1 d . . . . .
H4 H 0.7239 0.3700 0.3232 0.058 Uiso 1 1 calc R U . . .
N4 N 0.6284(7) 0.3054(8) 0.3988(6) 0.042(2) Uani 1 1 d . . . . .
C5 C 0.5124(9) 0.2961(8) 0.3958(6) 0.031(2) Uani 1 1 d . . . . .
S1 S 0.3361(3) 0.4724(4) 0.1586(2) 0.0759(12) Uani 1 1 d . . . . .
C6 C 0.4222(13) 0.5675(17) 0.1007(10) 0.107(6) Uani 1 1 d . . . . .
H6A H 0.3689 0.6106 0.0485 0.160 Uiso 1 1 calc R U . . .
H6B H 0.4686 0.6301 0.1430 0.160 Uiso 1 1 calc R U . . .
H6C H 0.4749 0.5122 0.0798 0.160 Uiso 1 1 calc R U . . .
N5 N 0.5655(9) -0.0495(8) 0.5881(7) 0.029(2) Uani 1 1 d . . . . .
C7 C 0.5990(12) -0.1114(13) 0.6684(10) 0.036(3) Uani 1 1 d . . . . .
H7 H 0.6270 -0.0683 0.7247 0.043 Uiso 1 1 calc R U . . .
N6 N 0.5899(8) -0.2417(9) 0.6631(7) 0.031(2) Uani 1 1 d . . . . .
C8 C 0.5454(12) -0.2654(11) 0.5719(9) 0.038(3) Uani 1 1 d . . . . .
N7 N 0.5182(12) -0.3808(10) 0.5317(8) 0.060(4) Uani 1 1 d . . . . .
C9 C 0.4732(17) -0.3718(14) 0.4417(11) 0.079(6) Uani 1 1 d . . . . .
H9 H 0.4469 -0.4490 0.4114 0.094 Uiso 1 1 calc R U . . .
N8 N 0.4592(13) -0.2671(11) 0.3859(8) 0.070(4) Uani 1 1 d . . . . .
C10 C 0.4894(14) -0.1556(12) 0.4267(10) 0.048(4) Uani 1 1 d . . . . .
C11 C 0.5301(12) -0.1470(10) 0.5218(9) 0.034(3) Uani 1 1 d . . . . .
S2 S 0.4762(4) -0.0167(4) 0.3584(2) 0.0661(12) Uani 1 1 d . . . . .
C12 C 0.4053(13) -0.0785(15) 0.2475(9) 0.062(4) Uani 1 1 d . . . . .
H12A H 0.3927 -0.0103 0.2027 0.092 Uiso 1 1 calc R U . . .
H12B H 0.4549 -0.1436 0.2325 0.092 Uiso 1 1 calc R U . . .
H12C H 0.3295 -0.1153 0.2466 0.092 Uiso 1 1 calc R U . . .
O1 O 0.3609(7) 0.1114(7) 0.5955(5) 0.057(2) Uani 1 1 d . . . . .
C19 C 0.3198(11) 0.0237(12) 0.6308(10) 0.060(3) Uani 1 1 d . . . . .
H19 H 0.3714 -0.0435 0.6569 0.072 Uiso 1 1 calc R U . . .
N13 N 0.2102(9) 0.0160(11) 0.6352(7) 0.065(3) Uani 1 1 d . . . . .
C20 C 0.1213(15) 0.1135(18) 0.5950(13) 0.098(7) Uani 1 1 d . . . . .
H20A H 0.1449 0.1938 0.6266 0.147 Uiso 1 1 calc R U . . .
H20B H 0.0452 0.0876 0.6012 0.147 Uiso 1 1 calc R U . . .
H20C H 0.1151 0.1238 0.5305 0.147 Uiso 1 1 calc R U . . .
C21 C 0.1689(15) -0.0962(13) 0.6763(11) 0.096(5) Uani 1 1 d . . . . .
H21A H 0.2353 -0.1528 0.7023 0.144 Uiso 1 1 calc R U . . .
H21B H 0.1087 -0.1410 0.6293 0.144 Uiso 1 1 calc R U . . .
H21C H 0.1357 -0.0682 0.7242 0.144 Uiso 1 1 calc R U . . .
O2 O 0.7201(8) 0.1548(8) 0.5486(6) 0.050(2) Uani 1 1 d D . . . .
HW2 H 0.754(9) 0.083(6) 0.536(7) 0.059 Uiso 1 1 d D U . . .
HW1 H 0.704(10) 0.212(8) 0.500(5) 0.059 Uiso 1 1 d D U . . .
N9 N 0.1107(9) 0.5466(9) 0.2615(7) 0.031(3) Uani 1 1 d . . . . .
C13 C 0.0818(11) 0.6097(13) 0.1819(9) 0.030(3) Uani 1 1 d . . . . .
H13 H 0.0588 0.5663 0.1255 0.036 Uiso 1 1 calc R U . . .
N10 N 0.0870(8) 0.7367(9) 0.1855(7) 0.032(3) Uani 1 1 d . . . . .
C14 C 0.1256(13) 0.7596(12) 0.2794(9) 0.039(3) Uani 1 1 d . . . . .
N11 N 0.1481(14) 0.8772(11) 0.3195(8) 0.066(4) Uani 1 1 d . . . . .
C15 C 0.1825(18) 0.8672(14) 0.4124(10) 0.083(6) Uani 1 1 d . . . . .
H15 H 0.1991 0.9447 0.4444 0.100 Uiso 1 1 calc R U . . .
N12 N 0.1961(14) 0.7628(11) 0.4651(8) 0.074(4) Uani 1 1 d . . . . .
C16 C 0.1735(14) 0.6489(12) 0.4218(9) 0.049(4) Uani 1 1 d . . . . .
C17 C 0.1382(12) 0.6441(11) 0.3252(9) 0.034(3) Uani 1 1 d . . . . .
S3 S 0.1838(4) 0.5091(4) 0.4879(2) 0.0593(11) Uani 1 1 d . . . . .
C18 C 0.2515(15) 0.5606(14) 0.6060(9) 0.073(5) Uani 1 1 d . . . . .
H18A H 0.2601 0.4879 0.6468 0.109 Uiso 1 1 calc R U . . .
H18B H 0.3289 0.5970 0.6117 0.109 Uiso 1 1 calc R U . . .
H18C H 0.2015 0.6241 0.6222 0.109 Uiso 1 1 calc R U . . .
O3 O 0.0798(7) 0.2419(8) 0.3657(5) 0.062(2) Uani 1 1 d . . . . .
O4 O -0.0745(11) 0.3459(12) 0.2967(9) 0.103(5) Uani 1 1 d . . . . .
N14 N -0.0291(9) 0.2668(11) 0.3559(8) 0.065(3) Uani 1 1 d . . . . .
O5 O -0.0817(9) 0.2136(11) 0.4036(7) 0.117(4) Uani 1 1 d . . . . .
O6 O 0.3385(11) 0.0715(12) 1.0309(9) 0.113(4) Uani 1 1 d . U . . .
C24 C 0.318(3) 0.181(3) 0.9999(19) 0.171(10) Uani 1 1 d . U . . .
H24 H 0.3002 0.2440 1.0376 0.205 Uiso 1 1 calc R U . . .
N15 N 0.3199(12) 0.2142(17) 0.9152(12) 0.107(5) Uani 1 1 d . U . . .
C22 C 0.289(4) 0.340(3) 0.883(3) 0.31(2) Uani 1 1 d . U . . .
H22A H 0.2730 0.3903 0.9318 0.466 Uiso 1 1 calc R U . . .
H22B H 0.3545 0.3782 0.8661 0.466 Uiso 1 1 calc R U . . .
H22C H 0.2192 0.3382 0.8306 0.466 Uiso 1 1 calc R U . . .
C23 C 0.345(4) 0.131(3) 0.865(2) 0.30(2) Uani 1 1 d . U . . .
H23A H 0.3427 0.1690 0.8067 0.456 Uiso 1 1 calc R U . . .
H23B H 0.4235 0.0982 0.8947 0.456 Uiso 1 1 calc R U . . .
H23C H 0.2874 0.0627 0.8555 0.456 Uiso 1 1 calc R U . . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Zn1 N10 2.006(9) 2_565 ?
Zn1 N5 2.013(9) . ?
Zn1 N1 2.029(7) . ?
Zn1 O2 2.160(9) . ?
Zn1 O1 2.324(8) . ?
Zn2 N9 1.998(9) . ?
Zn2 N6 2.005(10) 2_454 ?
Zn2 N2 2.042(7) . ?
Zn2 O3 2.061(8) . ?
N1 C1 1.321(14) . ?
N1 C5 1.376(11) . ?
C1 N2 1.344(14) . ?
C1 H1 0.9300 . ?
N2 C2 1.382(11) . ?
C2 C5 1.407(12) . ?
C2 C3 1.410(13) . ?
C3 N3 1.313(13) . ?
C3 S1 1.737(10) . ?
N3 C4 1.349(14) . ?
C4 N4 1.334(12) . ?
C4 H4 0.9300 . ?
N4 C5 1.345(12) . ?
S1 C6 1.808(13) . ?
C6 H6A 0.9600 . ?
C6 H6B 0.9600 . ?
C6 H6C 0.9600 . ?
N5 C7 1.325(15) . ?
N5 C11 1.398(14) . ?
C7 N6 1.358(13) . ?
C7 H7 0.9300 . ?
N6 C8 1.344(15) . ?
N6 Zn2 2.005(10) 2 ?
C8 N7 1.338(14) . ?
C8 C11 1.427(15) . ?
N7 C9 1.308(17) . ?
C9 N8 1.355(16) . ?
C9 H9 0.9300 . ?
N8 C10 1.311(15) . ?
C10 C11 1.375(17) . ?
C10 S2 1.754(13) . ?
S2 C12 1.757(13) . ?
C12 H12A 0.9600 . ?
C12 H12B 0.9600 . ?
C12 H12C 0.9600 . ?
O1 C19 1.221(13) . ?
C19 N13 1.303(14) . ?
C19 H19 0.9300 . ?
N13 C20 1.449(17) . ?
N13 C21 1.467(16) . ?
C20 H20A 0.9600 . ?
C20 H20B 0.9600 . ?
C20 H20C 0.9600 . ?
C21 H21A 0.9600 . ?
C21 H21B 0.9600 . ?
C21 H21C 0.9600 . ?
O2 HW2 0.89(3) . ?
O2 HW1 0.92(3) . ?
N9 C13 1.323(15) . ?
N9 C17 1.368(14) . ?
C13 N10 1.320(13) . ?
C13 H13 0.9300 . ?
N10 C14 1.376(15) . ?
N10 Zn1 2.006(9) 2_464 ?
C14 N11 1.354(14) . ?
C14 C17 1.370(16) . ?
N11 C15 1.345(17) . ?
C15 N12 1.326(17) . ?
C15 H15 0.9300 . ?
N12 C16 1.340(15) . ?
C16 C17 1.395(17) . ?
C16 S3 1.745(13) . ?
S3 C18 1.805(14) . ?
C18 H18A 0.9600 . ?
C18 H18B 0.9600 . ?
C18 H18C 0.9600 . ?
O3 N14 1.264(12) . ?
O4 N14 1.214(13) . ?
N14 O5 1.208(12) . ?
O6 C24 1.23(2) . ?
C24 N15 1.33(3) . ?
C24 H24 0.9300 . ?
N15 C23 1.23(3) . ?
N15 C22 1.40(3) . ?
C22 H22A 0.9600 . ?
C22 H22B 0.9600 . ?
C22 H22C 0.9600 . ?
C23 H23A 0.9600 . ?
C23 H23B 0.9600 . ?
C23 H23C 0.9600 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
N10 Zn1 N5 123.7(4) 2_565 . ?
N10 Zn1 N1 107.7(3) 2_565 . ?
N5 Zn1 N1 127.7(4) . . ?
N10 Zn1 O2 97.6(4) 2_565 . ?
N5 Zn1 O2 90.1(4) . . ?
N1 Zn1 O2 92.8(3) . . ?
N10 Zn1 O1 88.6(3) 2_565 . ?
N5 Zn1 O1 85.2(4) . . ?
N1 Zn1 O1 86.6(3) . . ?
O2 Zn1 O1 173.7(3) . . ?
N9 Zn2 N6 120.5(4) . 2_454 ?
N9 Zn2 N2 110.2(3) . . ?
N6 Zn2 N2 106.2(4) 2_454 . ?
N9 Zn2 O3 124.8(4) . . ?
N6 Zn2 O3 99.1(4) 2_454 . ?
N2 Zn2 O3 91.2(3) . . ?
C1 N1 C5 104.4(8) . . ?
C1 N1 Zn1 126.4(7) . . ?
C5 N1 Zn1 128.1(6) . . ?
N1 C1 N2 116.1(11) . . ?
N1 C1 H1 121.9 . . ?
N2 C1 H1 121.9 . . ?
C1 N2 C2 103.3(8) . . ?
C1 N2 Zn2 123.4(7) . . ?
C2 N2 Zn2 133.3(6) . . ?
N2 C2 C5 108.2(8) . . ?
N2 C2 C3 134.6(8) . . ?
C5 C2 C3 116.7(9) . . ?
N3 C3 C2 119.5(10) . . ?
N3 C3 S1 120.5(8) . . ?
C2 C3 S1 120.0(8) . . ?
C3 N3 C4 118.9(10) . . ?
N4 C4 N3 127.4(10) . . ?
N4 C4 H4 116.3 . . ?
N3 C4 H4 116.3 . . ?
C4 N4 C5 113.4(8) . . ?
N4 C5 N1 128.2(8) . . ?
N4 C5 C2 123.9(9) . . ?
N1 C5 C2 107.9(8) . . ?
C3 S1 C6 102.0(6) . . ?
S1 C6 H6A 109.5 . . ?
S1 C6 H6B 109.5 . . ?
H6A C6 H6B 109.5 . . ?
S1 C6 H6C 109.5 . . ?
H6A C6 H6C 109.5 . . ?
H6B C6 H6C 109.5 . . ?
C7 N5 C11 104.4(10) . . ?
C7 N5 Zn1 123.8(8) . . ?
C11 N5 Zn1 131.1(8) . . ?
N5 C7 N6 115.7(11) . . ?
N5 C7 H7 122.2 . . ?
N6 C7 H7 122.2 . . ?
C8 N6 C7 104.1(10) . . ?
C8 N6 Zn2 132.8(8) . 2 ?
C7 N6 Zn2 123.1(8) . 2 ?
N7 C8 N6 126.7(11) . . ?
N7 C8 C11 123.7(13) . . ?
N6 C8 C11 109.6(11) . . ?
C9 N7 C8 112.1(12) . . ?
N7 C9 N8 129.9(14) . . ?
N7 C9 H9 115.1 . . ?
N8 C9 H9 115.1 . . ?
C10 N8 C9 116.7(13) . . ?
N8 C10 C11 120.7(12) . . ?
N8 C10 S2 119.0(11) . . ?
C11 C10 S2 120.3(10) . . ?
C10 C11 N5 137.1(11) . . ?
C10 C11 C8 116.6(11) . . ?
N5 C11 C8 106.3(12) . . ?
C10 S2 C12 101.3(7) . . ?
S2 C12 H12A 109.5 . . ?
S2 C12 H12B 109.5 . . ?
H12A C12 H12B 109.5 . . ?
S2 C12 H12C 109.5 . . ?
H12A C12 H12C 109.5 . . ?
H12B C12 H12C 109.5 . . ?
C19 O1 Zn1 131.8(8) . . ?
O1 C19 N13 125.8(12) . . ?
O1 C19 H19 117.1 . . ?
N13 C19 H19 117.1 . . ?
C19 N13 C20 122.0(12) . . ?
C19 N13 C21 121.3(12) . . ?
C20 N13 C21 116.6(12) . . ?
N13 C20 H20A 109.5 . . ?
N13 C20 H20B 109.5 . . ?
H20A C20 H20B 109.5 . . ?
N13 C20 H20C 109.5 . . ?
H20A C20 H20C 109.5 . . ?
H20B C20 H20C 109.5 . . ?
N13 C21 H21A 109.5 . . ?
N13 C21 H21B 109.5 . . ?
H21A C21 H21B 109.5 . . ?
N13 C21 H21C 109.5 . . ?
H21A C21 H21C 109.5 . . ?
H21B C21 H21C 109.5 . . ?
Zn1 O2 HW2 119(7) . . ?
Zn1 O2 HW1 102(7) . . ?
HW2 O2 HW1 111(6) . . ?
C13 N9 C17 102.4(10) . . ?
C13 N9 Zn2 124.9(8) . . ?
C17 N9 Zn2 131.6(8) . . ?
N10 C13 N9 117.5(11) . . ?
N10 C13 H13 121.2 . . ?
N9 C13 H13 121.2 . . ?
C13 N10 C14 102.2(10) . . ?
C13 N10 Zn1 126.2(8) . 2_464 ?
C14 N10 Zn1 131.6(8) . 2_464 ?
N11 C14 C17 125.9(13) . . ?
N11 C14 N10 125.3(12) . . ?
C17 C14 N10 108.8(11) . . ?
C15 N11 C14 110.8(12) . . ?
N12 C15 N11 129.4(13) . . ?
N12 C15 H15 115.3 . . ?
N11 C15 H15 115.3 . . ?
C15 N12 C16 117.3(12) . . ?
N12 C16 C17 119.8(12) . . ?
N12 C16 S3 119.0(11) . . ?
C17 C16 S3 121.2(10) . . ?
N9 C17 C14 109.0(12) . . ?
N9 C17 C16 134.2(11) . . ?
C14 C17 C16 116.8(12) . . ?
C16 S3 C18 104.7(7) . . ?
S3 C18 H18A 109.5 . . ?
S3 C18 H18B 109.5 . . ?
H18A C18 H18B 109.5 . . ?
S3 C18 H18C 109.5 . . ?
H18A C18 H18C 109.5 . . ?
H18B C18 H18C 109.5 . . ?
N14 O3 Zn2 108.0(7) . . ?
O5 N14 O4 124.0(12) . . ?
O5 N14 O3 120.5(11) . . ?
O4 N14 O3 115.5(10) . . ?
O6 C24 N15 123(2) . . ?
O6 C24 H24 118.3 . . ?
N15 C24 H24 118.3 . . ?
C23 N15 C24 119(2) . . ?
C23 N15 C22 122(3) . . ?
C24 N15 C22 120(2) . . ?
N15 C22 H22A 109.5 . . ?
N15 C22 H22B 109.5 . . ?
H22A C22 H22B 109.5 . . ?
N15 C22 H22C 109.5 . . ?
H22A C22 H22C 109.5 . . ?
H22B C22 H22C 109.5 . . ?
N15 C23 H23A 109.5 . . ?
N15 C23 H23B 109.5 . . ?
H23A C23 H23B 109.5 . . ?
N15 C23 H23C 109.5 . . ?
H23A C23 H23C 109.5 . . ?
H23B C23 H23C 109.5 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C5 N1 C1 N2 -0.8(13) . . . . ?
Zn1 N1 C1 N2 -169.8(7) . . . . ?
N1 C1 N2 C2 1.1(13) . . . . ?
N1 C1 N2 Zn2 -177.2(7) . . . . ?
C1 N2 C2 C5 -0.9(10) . . . . ?
Zn2 N2 C2 C5 177.1(6) . . . . ?
C1 N2 C2 C3 -173.1(12) . . . . ?
Zn2 N2 C2 C3 4.9(16) . . . . ?
N2 C2 C3 N3 176.7(10) . . . . ?
C5 C2 C3 N3 5.0(15) . . . . ?
N2 C2 C3 S1 -2.8(16) . . . . ?
C5 C2 C3 S1 -174.5(7) . . . . ?
C2 C3 N3 C4 -2.3(17) . . . . ?
S1 C3 N3 C4 177.3(9) . . . . ?
C3 N3 C4 N4 -1.1(19) . . . . ?
N3 C4 N4 C5 1.3(16) . . . . ?
C4 N4 C5 N1 -177.3(9) . . . . ?
C4 N4 C5 C2 1.9(14) . . . . ?
C1 N1 C5 N4 179.4(10) . . . . ?
Zn1 N1 C5 N4 -11.8(14) . . . . ?
C1 N1 C5 C2 0.1(10) . . . . ?
Zn1 N1 C5 C2 168.9(6) . . . . ?
N2 C2 C5 N4 -178.8(8) . . . . ?
C3 C2 C5 N4 -5.0(14) . . . . ?
N2 C2 C5 N1 0.5(10) . . . . ?
C3 C2 C5 N1 174.3(8) . . . . ?
N3 C3 S1 C6 -10.4(12) . . . . ?
C2 C3 S1 C6 169.2(10) . . . . ?
C11 N5 C7 N6 0.1(16) . . . . ?
Zn1 N5 C7 N6 171.6(8) . . . . ?
N5 C7 N6 C8 -0.8(15) . . . . ?
N5 C7 N6 Zn2 179.7(9) . . . 2 ?
C7 N6 C8 N7 -178.6(15) . . . . ?
Zn2 N6 C8 N7 1(2) 2 . . . ?
C7 N6 C8 C11 1.2(15) . . . . ?
Zn2 N6 C8 C11 -179.4(9) 2 . . . ?
N6 C8 N7 C9 178.1(15) . . . . ?
C11 C8 N7 C9 -2(2) . . . . ?
C8 N7 C9 N8 5(3) . . . . ?
N7 C9 N8 C10 -4(3) . . . . ?
C9 N8 C10 C11 -2(2) . . . . ?
C9 N8 C10 S2 178.8(13) . . . . ?
N8 C10 C11 N5 -177.4(16) . . . . ?
S2 C10 C11 N5 2(3) . . . . ?
N8 C10 C11 C8 4(2) . . . . ?
S2 C10 C11 C8 -176.1(11) . . . . ?
C7 N5 C11 C10 -177.6(18) . . . . ?
Zn1 N5 C11 C10 12(3) . . . . ?
C7 N5 C11 C8 0.7(16) . . . . ?
Zn1 N5 C11 C8 -170.0(8) . . . . ?
N7 C8 C11 C10 -3(2) . . . . ?
N6 C8 C11 C10 177.5(12) . . . . ?
N7 C8 C11 N5 178.6(13) . . . . ?
N6 C8 C11 N5 -1.2(17) . . . . ?
N8 C10 S2 C12 6.3(16) . . . . ?
C11 C10 S2 C12 -173.1(13) . . . . ?
Zn1 O1 C19 N13 -178.3(9) . . . . ?
O1 C19 N13 C20 1(2) . . . . ?
O1 C19 N13 C21 177.7(13) . . . . ?
C17 N9 C13 N10 0.0(15) . . . . ?
Zn2 N9 C13 N10 -169.4(8) . . . . ?
N9 C13 N10 C14 0.8(14) . . . . ?
N9 C13 N10 Zn1 179.7(8) . . . 2_464 ?
C13 N10 C14 N11 178.2(15) . . . . ?
Zn1 N10 C14 N11 -1(2) 2_464 . . . ?
C13 N10 C14 C17 -1.3(15) . . . . ?
Zn1 N10 C14 C17 179.9(9) 2_464 . . . ?
C17 C14 N11 C15 -2(2) . . . . ?
N10 C14 N11 C15 178.9(15) . . . . ?
C14 N11 C15 N12 0(3) . . . . ?
N11 C15 N12 C16 0(3) . . . . ?
C15 N12 C16 C17 1(2) . . . . ?
C15 N12 C16 S3 -177.3(14) . . . . ?
C13 N9 C17 C14 -0.8(16) . . . . ?
Zn2 N9 C17 C14 167.6(8) . . . . ?
C13 N9 C17 C16 178.5(17) . . . . ?
Zn2 N9 C17 C16 -13(2) . . . . ?
N11 C14 C17 N9 -178.1(13) . . . . ?
N10 C14 C17 N9 1.4(17) . . . . ?
N11 C14 C17 C16 2(2) . . . . ?
N10 C14 C17 C16 -178.1(12) . . . . ?
N12 C16 C17 N9 179.0(15) . . . . ?
S3 C16 C17 N9 -3(3) . . . . ?
N12 C16 C17 C14 -2(2) . . . . ?
S3 C16 C17 C14 176.1(11) . . . . ?
N12 C16 S3 C18 -9.9(16) . . . . ?
C17 C16 S3 C18 172.3(13) . . . . ?
Zn2 O3 N14 O5 -178.3(11) . . . . ?
Zn2 O3 N14 O4 1.7(14) . . . . ?
O6 C24 N15 C23 -1(4) . . . . ?
O6 C24 N15 C22 177(3) . . . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
C1 H1 O1 0.93 2.38 2.960(15) 120.6 .
C1 H1 O3 0.93 2.48 2.999(14) 115.5 .
C7 H7 N11 0.93 2.42 3.267(18) 152.0 2_565
C13 H13 N7 0.93 2.36 3.218(18) 154.1 2_454
C4 H4 O4 0.93 2.51 3.426(15) 167.4 1_655
O2 HW2 O6 0.89(3) 1.89(3) 2.779(13) 171(9) 2_554
O2 HW1 N4 0.92(3) 1.80(5) 2.698(11) 163(11) .

_refine_diff_density_max         0.485
_refine_diff_density_min         -0.259
_refine_diff_density_rms         0.066

_shelxl_version_number           2014/6

####################################################################### 
# 
# 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_shelx
_database_code_depnum_ccdc_archive 'CCDC 1411215'

_audit_update_record             
;
2015-09-28 deposited with the CCDC.
2015-12-14 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/6
_chemical_name_systematic        'Desolvated UZAR-S12'
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C21 H24 N14 O5 S3 Zn2'
_chemical_formula_sum            'C21 H24 N14 O5 S3 Zn2'
_chemical_formula_weight         779.46

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'

_space_group_crystal_system      monoclinic
_space_group_IT_number           7
_space_group_name_H-M_alt        'P n'
_space_group_name_Hall           'P -2yac'

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

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

_cell_length_a                   11.6757(8)
_cell_length_b                   10.3908(4)
_cell_length_c                   15.1045(7)
_cell_angle_alpha                90
_cell_angle_beta                 107.129(6)
_cell_angle_gamma                90
_cell_volume                     1751.19(17)
_cell_formula_units_Z            2
_cell_measurement_temperature    296(1)
_cell_measurement_reflns_used    2030
_cell_measurement_theta_min      3.4290
_cell_measurement_theta_max      21.7860


_exptl_crystal_description       block
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.478
_exptl_crystal_F_000             792
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.200
_exptl_crystal_size_mid          0.040
_exptl_crystal_size_min          0.020
_exptl_absorpt_coefficient_mu    1.600
_shelx_estimated_absorpt_T_min   0.740
_shelx_estimated_absorpt_T_max   0.969
_exptl_absorpt_correction_T_min  0.98591
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.31 (release 14-01-2014 CrysAlis171 .NET)
(compiled Jan 14 2014,18:38:05)
Multi-scan absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      296(1)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'Enhance (Mo) X-ray Source'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'Xcalibur, Sapphire3'
_diffrn_detector                 'CCD plate'
_diffrn_detector_type            Sapphire3
_diffrn_measurement_method       ω-scans
_diffrn_detector_area_resol_mean 16.3990
_diffrn_reflns_number            18164
_diffrn_reflns_av_unetI/netI     0.1439
_diffrn_reflns_av_R_equivalents  0.0996
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_theta_min         3.269
_diffrn_reflns_theta_max         24.997
_diffrn_reflns_theta_full        25.000
_diffrn_measured_fraction_theta_max 0.995
_diffrn_measured_fraction_theta_full 0.995
_diffrn_reflns_Laue_measured_fraction_max 0.995
_diffrn_reflns_Laue_measured_fraction_full 0.995
_diffrn_reflns_point_group_measured_fraction_max 0.993
_diffrn_reflns_point_group_measured_fraction_full 0.993
_reflns_number_total             6141
_reflns_number_gt                3599
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.992
_reflns_Friedel_fraction_max     0.991
_reflns_Friedel_fraction_full    0.991

_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 Structure factors included contributions from the .fab file.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_computing_data_collection       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.31 (release 14-01-2014 CrysAlis171 .NET)
(compiled Jan 14 2014,18:38:05)
;
_computing_cell_refinement       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.31 (release 14-01-2014 CrysAlis171 .NET)
(compiled Jan 14 2014,18:38:05)
;
_computing_data_reduction        
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.31 (release 14-01-2014 CrysAlis171 .NET)
(compiled Jan 14 2014,18:38:05)
;
_computing_structure_solution    
; 
SIR92
A. Altomare, G. Cascarano, C. Giacovazzo and A. Guagliardi, J. Appl.
 Crystallogr., 1994, 27, 435.
;
_computing_structure_refinement  'SHELXL-2014/6 (Sheldrick, 2014)'
_computing_molecular_graphics    Diamond
_computing_publication_material  'SHELXL-2014/6 (Sheldrick, 2014)'
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0452P)²] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_abs_structure_details 
;
 Flack x determined using 1220 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.27(2)
_chemical_absolute_configuration ?
_refine_ls_number_reflns         6141
_refine_ls_number_parameters     408
_refine_ls_number_restraints     314
_refine_ls_R_factor_all          0.1311
_refine_ls_R_factor_gt           0.0704
_refine_ls_wR_factor_ref         0.1546
_refine_ls_wR_factor_gt          0.1284
_refine_ls_goodness_of_fit_ref   1.007
_refine_ls_restrained_S_all      0.985
_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_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 0.39183(13) 1.14332(18) 0.73755(10) 0.0379(7) Uani 1 1 d . . . . .
Zn2 Zn 0.30580(13) 0.64391(17) 0.53947(10) 0.0343(6) Uani 1 1 d . . . . .
N1 N 0.3738(15) 0.9512(12) 0.7253(10) 0.034(4) Uani 1 1 d . U . . .
C1 C 0.3420(18) 0.8884(17) 0.6455(14) 0.030(4) Uani 1 1 d . U . . .
H1 H 0.3156 0.9311 0.5890 0.035 Uiso 1 1 calc R U . . .
N2 N 0.3499(12) 0.7594(13) 0.6508(10) 0.034(4) Uani 1 1 d . U . . .
C2 C 0.393(2) 0.7406(16) 0.7417(13) 0.042(5) Uani 1 1 d . U . . .
N3 N 0.4183(19) 0.6204(14) 0.7853(11) 0.070(7) Uani 1 1 d . U . . .
C3 C 0.465(2) 0.6314(18) 0.8747(14) 0.071(8) Uani 1 1 d . U . . .
H3 H 0.4924 0.5545 0.9052 0.085 Uiso 1 1 calc R U . . .
N4 N 0.4812(17) 0.7348(14) 0.9302(10) 0.064(5) Uani 1 1 d . U . . .
C4 C 0.448(2) 0.8476(17) 0.8871(15) 0.058(7) Uani 1 1 d . U . . .
C5 C 0.4077(18) 0.8544(15) 0.7886(13) 0.035(5) Uani 1 1 d . U . . .
S1 S 0.4654(6) 0.9831(5) 0.9552(3) 0.074(2) Uani 1 1 d . U . . .
C6 C 0.5347(19) 0.924(2) 1.0679(12) 0.066(6) Uani 1 1 d . U . . .
H6A H 0.5481 0.9935 1.1115 0.099 Uiso 1 1 calc R U . . .
H6B H 0.4836 0.8608 1.0836 0.099 Uiso 1 1 calc R U . . .
H6C H 0.6099 0.8847 1.0700 0.099 Uiso 1 1 calc R U . . .
N5 N 0.4754(10) 1.2508(11) 0.8529(8) 0.035(3) Uani 1 1 d . . . . .
C7 C 0.0928(19) 0.740(2) 0.3887(14) 0.040(3) Uani 1 1 d . U . . .
H7 H 0.1465 0.7706 0.3586 0.048 Uiso 1 1 calc R U . . .
N6 N 0.1283(11) 0.6828(11) 0.4731(8) 0.040(3) Uani 1 1 d . U . . .
C8 C -0.0703(14) 0.7036(13) 0.4198(10) 0.033(3) Uani 1 1 d . U . . .
N7 N -0.1849(11) 0.6940(11) 0.4169(9) 0.045(3) Uani 1 1 d . U . . .
C9 C -0.2029(15) 0.6403(15) 0.4889(12) 0.057(5) Uani 1 1 d . U . . .
H9 H -0.2822 0.6382 0.4898 0.068 Uiso 1 1 calc R U . . .
N8 N -0.1235(15) 0.5876(15) 0.5621(11) 0.056(4) Uani 1 1 d . U . . .
C10 C -0.0070(17) 0.5989(16) 0.5634(11) 0.044(4) Uani 1 1 d . U . . .
C11 C 0.0227(13) 0.6602(13) 0.4945(10) 0.032(3) Uani 1 1 d . U . . .
S2 S 0.1049(5) 0.5277(6) 0.6565(4) 0.0803(19) Uani 1 1 d . U . . .
C12 C 0.0214(19) 0.433(2) 0.7115(15) 0.109(9) Uani 1 1 d . U . . .
H12A H 0.0747 0.3898 0.7636 0.164 Uiso 1 1 calc R U . . .
H12B H -0.0323 0.4871 0.7322 0.164 Uiso 1 1 calc R U . . .
H12C H -0.0240 0.3704 0.6685 0.164 Uiso 1 1 calc R U . . .
N9 N 0.3269(14) 0.4543(13) 0.5510(11) 0.039(4) Uani 1 1 d . U . . .
C13 C 0.360(2) 0.3908(18) 0.6326(15) 0.044(5) Uani 1 1 d . U . . .
H13 H 0.3862 0.4342 0.6887 0.052 Uiso 1 1 calc R U . . .
N10 N 0.3516(14) 0.2612(13) 0.6287(10) 0.041(4) Uani 1 1 d . U . . .
C14 C 0.3122(19) 0.2354(17) 0.5328(13) 0.038(4) Uani 1 1 d . U . . .
N11 N 0.2875(18) 0.1221(15) 0.4972(12) 0.057(5) Uani 1 1 d . U . . .
C15 C 0.263(3) 0.126(2) 0.4038(16) 0.093(10) Uani 1 1 d . U . . .
H15 H 0.2569 0.0471 0.3732 0.111 Uiso 1 1 calc R U . . .
N12 N 0.2471(18) 0.2365(16) 0.3492(11) 0.078(6) Uani 1 1 d . U . . .
C16 C 0.261(2) 0.3519(17) 0.3908(14) 0.048(5) Uani 1 1 d . U . . .
C17 C 0.3004(19) 0.3561(17) 0.4872(14) 0.041(5) Uani 1 1 d . U . . .
S3 S 0.2587(6) 0.4916(5) 0.3268(3) 0.0630(17) Uani 1 1 d . U . . .
C18 C 0.187(2) 0.4367(19) 0.2092(13) 0.075(7) Uani 1 1 d . U . . .
H18A H 0.1810 0.5072 0.1670 0.113 Uiso 1 1 calc R U . . .
H18B H 0.2345 0.3693 0.1939 0.113 Uiso 1 1 calc R U . . .
H18C H 0.1087 0.4045 0.2047 0.113 Uiso 1 1 calc R U . . .
O1 O 0.5814(12) 1.1138(12) 0.7176(9) 0.069(4) Uani 1 1 d . . . . .
C19 C 0.619(2) 1.024(2) 0.6842(14) 0.074(6) Uani 1 1 d . . . . .
H19 H 0.5678 0.9572 0.6578 0.089 Uiso 1 1 calc R U . . .
N13 N 0.7372(17) 1.0189(17) 0.6843(11) 0.077(5) Uani 1 1 d . . . . .
C20 C 0.776(2) 0.900(2) 0.641(2) 0.127(10) Uani 1 1 d . . . . .
H20A H 0.7975 0.9254 0.5866 0.190 Uiso 1 1 calc R U . . .
H20B H 0.7108 0.8399 0.6235 0.190 Uiso 1 1 calc R U . . .
H20C H 0.8436 0.8610 0.6845 0.190 Uiso 1 1 calc R U . . .
C21 C 0.812(2) 1.118(3) 0.7148(18) 0.105(10) Uani 1 1 d . . . . .
H21A H 0.7664 1.1945 0.7161 0.157 Uiso 1 1 calc R U . . .
H21B H 0.8604 1.1310 0.6740 0.157 Uiso 1 1 calc R U . . .
H21C H 0.8629 1.0998 0.7761 0.157 Uiso 1 1 calc R U . . .
O2 O 0.2260(13) 1.1529(11) 0.7695(10) 0.064(4) Uani 1 1 d . . . . .
O3 O 0.3605(11) 0.7595(12) 0.4491(8) 0.069(4) Uani 1 1 d . . . . .
N14 N 0.4675(17) 0.7345(16) 0.4584(11) 0.067(4) Uani 1 1 d . . . . .
O4 O 0.5116(15) 0.6544(16) 0.5181(11) 0.088(6) Uani 1 1 d . . . . .
O5 O 0.5277(13) 0.7863(15) 0.4124(11) 0.113(6) 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
Zn1 N10 1.993(14) 1_565 ?
Zn1 N1 2.010(13) . ?
Zn1 N5 2.058(11) . ?
Zn1 O2 2.131(15) . ?
Zn1 O1 2.341(13) . ?
Zn2 N9 1.987(13) . ?
Zn2 N2 2.006(14) . ?
Zn2 O3 2.055(13) . ?
Zn2 N6 2.060(12) . ?
N1 C1 1.32(2) . ?
N1 C5 1.36(2) . ?
C1 N2 1.345(18) . ?
C1 H1 0.9300 . ?
N2 C2 1.33(2) . ?
C2 C5 1.36(2) . ?
C2 N3 1.40(2) . ?
N3 C3 1.30(2) . ?
C3 N4 1.34(2) . ?
C3 H3 0.9300 . ?
N4 C4 1.34(2) . ?
C4 C5 1.42(2) . ?
C4 S1 1.72(2) . ?
S1 C6 1.768(19) . ?
C6 H6A 0.9600 . ?
C6 H6B 0.9600 . ?
C6 H6C 0.9600 . ?
N5 C7 1.32(2) 2_575 ?
N5 C8 1.358(17) 2_575 ?
C7 N5 1.32(2) 2_474 ?
C7 N6 1.36(2) . ?
C7 H7 0.9300 . ?
N6 C11 1.384(17) . ?
C8 N7 1.330(18) . ?
C8 N5 1.358(17) 2_474 ?
C8 C11 1.391(18) . ?
N7 C9 1.294(18) . ?
C9 N8 1.33(2) . ?
C9 H9 0.9300 . ?
N8 C10 1.36(2) . ?
C10 C11 1.35(2) . ?
C10 S2 1.775(16) . ?
S2 C12 1.756(19) . ?
C12 H12A 0.9600 . ?
C12 H12B 0.9600 . ?
C12 H12C 0.9600 . ?
N9 C13 1.35(2) . ?
N9 C17 1.37(2) . ?
C13 N10 1.350(19) . ?
C13 H13 0.9300 . ?
N10 C14 1.41(2) . ?
N10 Zn1 1.993(14) 1_545 ?
C14 N11 1.29(2) . ?
C14 C17 1.42(2) . ?
N11 C15 1.35(2) . ?
C15 N12 1.40(2) . ?
C15 H15 0.9300 . ?
N12 C16 1.34(2) . ?
C16 C17 1.39(3) . ?
C16 S3 1.740(19) . ?
S3 C18 1.82(2) . ?
C18 H18A 0.9600 . ?
C18 H18B 0.9600 . ?
C18 H18C 0.9600 . ?
O1 C19 1.20(2) . ?
C19 N13 1.38(2) . ?
C19 H19 0.9300 . ?
N13 C21 1.34(2) . ?
N13 C20 1.53(2) . ?
C20 H20A 0.9600 . ?
C20 H20B 0.9600 . ?
C20 H20C 0.9600 . ?
C21 H21A 0.9600 . ?
C21 H21B 0.9600 . ?
C21 H21C 0.9600 . ?
O3 N14 1.242(18) . ?
N14 O4 1.225(19) . ?
N14 O5 1.246(18) . ?

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
N10 Zn1 N1 122.8(6) 1_565 . ?
N10 Zn1 N5 107.6(5) 1_565 . ?
N1 Zn1 N5 128.9(5) . . ?
N10 Zn1 O2 98.6(6) 1_565 . ?
N1 Zn1 O2 89.4(6) . . ?
N5 Zn1 O2 91.1(5) . . ?
N10 Zn1 O1 88.6(6) 1_565 . ?
N1 Zn1 O1 86.3(6) . . ?
N5 Zn1 O1 87.1(5) . . ?
O2 Zn1 O1 172.8(5) . . ?
N9 Zn2 N2 121.7(6) . . ?
N9 Zn2 O3 125.6(6) . . ?
N2 Zn2 O3 98.9(5) . . ?
N9 Zn2 N6 108.6(6) . . ?
N2 Zn2 N6 105.3(5) . . ?
O3 Zn2 N6 91.5(5) . . ?
C1 N1 C5 102.8(14) . . ?
C1 N1 Zn1 124.5(12) . . ?
C5 N1 Zn1 131.8(13) . . ?
N1 C1 N2 116.2(16) . . ?
N1 C1 H1 121.9 . . ?
N2 C1 H1 121.9 . . ?
C2 N2 C1 101.9(15) . . ?
C2 N2 Zn2 134.7(12) . . ?
C1 N2 Zn2 123.4(13) . . ?
N2 C2 C5 111.1(17) . . ?
N2 C2 N3 125.4(16) . . ?
C5 C2 N3 123.5(18) . . ?
C3 N3 C2 112.0(16) . . ?
N3 C3 N4 131.0(19) . . ?
N3 C3 H3 114.5 . . ?
N4 C3 H3 114.5 . . ?
C3 N4 C4 115.4(18) . . ?
N4 C4 C5 120.7(18) . . ?
N4 C4 S1 117.3(17) . . ?
C5 C4 S1 121.9(13) . . ?
N1 C5 C2 108.0(18) . . ?
N1 C5 C4 135.1(16) . . ?
C2 C5 C4 116.9(17) . . ?
C4 S1 C6 103.3(11) . . ?
S1 C6 H6A 109.5 . . ?
S1 C6 H6B 109.5 . . ?
H6A C6 H6B 109.5 . . ?
S1 C6 H6C 109.5 . . ?
H6A C6 H6C 109.5 . . ?
H6B C6 H6C 109.5 . . ?
C7 N5 C8 105.0(14) 2_575 2_575 ?
C7 N5 Zn1 124.1(12) 2_575 . ?
C8 N5 Zn1 128.8(10) 2_575 . ?
N5 C7 N6 114.0(18) 2_474 . ?
N5 C7 H7 123.0 2_474 . ?
N6 C7 H7 123.0 . . ?
C7 N6 C11 104.4(14) . . ?
C7 N6 Zn2 121.9(12) . . ?
C11 N6 Zn2 133.7(9) . . ?
N7 C8 N5 127.8(13) . 2_474 ?
N7 C8 C11 122.6(14) . . ?
N5 C8 C11 109.5(14) 2_474 . ?
C9 N7 C8 114.6(14) . . ?
N7 C9 N8 128.9(17) . . ?
N7 C9 H9 115.5 . . ?
N8 C9 H9 115.5 . . ?
C9 N8 C10 115.2(16) . . ?
C11 C10 N8 120.8(16) . . ?
C11 C10 S2 120.7(14) . . ?
N8 C10 S2 118.4(13) . . ?
C10 C11 N6 135.2(14) . . ?
C10 C11 C8 117.6(15) . . ?
N6 C11 C8 106.9(13) . . ?
C12 S2 C10 103.1(9) . . ?
S2 C12 H12A 109.5 . . ?
S2 C12 H12B 109.5 . . ?
H12A C12 H12B 109.5 . . ?
S2 C12 H12C 109.5 . . ?
H12A C12 H12C 109.5 . . ?
H12B C12 H12C 109.5 . . ?
C13 N9 C17 102.8(15) . . ?
C13 N9 Zn2 124.0(13) . . ?
C17 N9 Zn2 132.7(13) . . ?
N9 C13 N10 116.8(18) . . ?
N9 C13 H13 121.6 . . ?
N10 C13 H13 121.6 . . ?
C13 N10 C14 103.4(15) . . ?
C13 N10 Zn1 125.5(13) . 1_545 ?
C14 N10 Zn1 131.1(11) . 1_545 ?
N11 C14 N10 124.5(17) . . ?
N11 C14 C17 128.8(19) . . ?
N10 C14 C17 106.6(16) . . ?
C14 N11 C15 111.2(18) . . ?
N11 C15 N12 126(2) . . ?
N11 C15 H15 117.0 . . ?
N12 C15 H15 117.0 . . ?
C16 N12 C15 119.0(19) . . ?
N12 C16 C17 118.4(18) . . ?
N12 C16 S3 120.4(17) . . ?
C17 C16 S3 120.1(14) . . ?
N9 C17 C16 133.9(16) . . ?
N9 C17 C14 110.3(19) . . ?
C16 C17 C14 115.8(17) . . ?
C16 S3 C18 102.1(10) . . ?
S3 C18 H18A 109.5 . . ?
S3 C18 H18B 109.5 . . ?
H18A C18 H18B 109.5 . . ?
S3 C18 H18C 109.5 . . ?
H18A C18 H18C 109.5 . . ?
H18B C18 H18C 109.5 . . ?
C19 O1 Zn1 129.3(14) . . ?
O1 C19 N13 121(2) . . ?
O1 C19 H19 119.3 . . ?
N13 C19 H19 119.3 . . ?
C21 N13 C19 121(2) . . ?
C21 N13 C20 121.5(19) . . ?
C19 N13 C20 117.0(18) . . ?
N13 C20 H20A 109.5 . . ?
N13 C20 H20B 109.5 . . ?
H20A C20 H20B 109.5 . . ?
N13 C20 H20C 109.5 . . ?
H20A C20 H20C 109.5 . . ?
H20B C20 H20C 109.5 . . ?
N13 C21 H21A 109.5 . . ?
N13 C21 H21B 109.5 . . ?
H21A C21 H21B 109.5 . . ?
N13 C21 H21C 109.5 . . ?
H21A C21 H21C 109.5 . . ?
H21B C21 H21C 109.5 . . ?
N14 O3 Zn2 107.6(11) . . ?
O4 N14 O3 114.5(18) . . ?
O4 N14 O5 121.3(19) . . ?
O3 N14 O5 124.1(17) . . ?

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
C5 N1 C1 N2 1(2) . . . . ?
Zn1 N1 C1 N2 171.5(13) . . . . ?
N1 C1 N2 C2 -2(2) . . . . ?
N1 C1 N2 Zn2 179.7(13) . . . . ?
C1 N2 C2 C5 1(2) . . . . ?
Zn2 N2 C2 C5 179.9(14) . . . . ?
C1 N2 C2 N3 180(2) . . . . ?
Zn2 N2 C2 N3 -2(3) . . . . ?
N2 C2 N3 C3 177(2) . . . . ?
C5 C2 N3 C3 -5(3) . . . . ?
C2 N3 C3 N4 8(4) . . . . ?
N3 C3 N4 C4 -3(4) . . . . ?
C3 N4 C4 C5 -4(4) . . . . ?
C3 N4 C4 S1 179.4(19) . . . . ?
C1 N1 C5 C2 0(2) . . . . ?
Zn1 N1 C5 C2 -169.4(13) . . . . ?
C1 N1 C5 C4 -178(3) . . . . ?
Zn1 N1 C5 C4 13(4) . . . . ?
N2 C2 C5 N1 -1(3) . . . . ?
N3 C2 C5 N1 -179.2(19) . . . . ?
N2 C2 C5 C4 177.1(19) . . . . ?
N3 C2 C5 C4 -1(4) . . . . ?
N4 C4 C5 N1 -177(2) . . . . ?
S1 C4 C5 N1 0(4) . . . . ?
N4 C4 C5 C2 6(4) . . . . ?
S1 C4 C5 C2 -177.7(18) . . . . ?
N4 C4 S1 C6 4(2) . . . . ?
C5 C4 S1 C6 -173(2) . . . . ?
N5 C7 N6 C11 -4(2) 2_474 . . . ?
N5 C7 N6 Zn2 175.1(11) 2_474 . . . ?
N5 C8 N7 C9 176.4(15) 2_474 . . . ?
C11 C8 N7 C9 0(2) . . . . ?
C8 N7 C9 N8 -4(3) . . . . ?
N7 C9 N8 C10 4(3) . . . . ?
C9 N8 C10 C11 0(3) . . . . ?
C9 N8 C10 S2 -178.3(13) . . . . ?
N8 C10 C11 N6 -176.5(15) . . . . ?
S2 C10 C11 N6 2(3) . . . . ?
N8 C10 C11 C8 -4(2) . . . . ?
S2 C10 C11 C8 174.4(10) . . . . ?
C7 N6 C11 C10 174.2(19) . . . . ?
Zn2 N6 C11 C10 -4(3) . . . . ?
C7 N6 C11 C8 1.2(16) . . . . ?
Zn2 N6 C11 C8 -177.2(10) . . . . ?
N7 C8 C11 C10 4(2) . . . . ?
N5 C8 C11 C10 -173.1(13) 2_474 . . . ?
N7 C8 C11 N6 178.7(12) . . . . ?
N5 C8 C11 N6 1.3(15) 2_474 . . . ?
C11 C10 S2 C12 -167.6(15) . . . . ?
N8 C10 S2 C12 10.9(17) . . . . ?
C17 N9 C13 N10 -3(3) . . . . ?
Zn2 N9 C13 N10 169.8(14) . . . . ?
N9 C13 N10 C14 2(2) . . . . ?
N9 C13 N10 Zn1 -179.3(14) . . . 1_545 ?
C13 N10 C14 N11 -177(2) . . . . ?
Zn1 N10 C14 N11 4(3) 1_545 . . . ?
C13 N10 C14 C17 0(2) . . . . ?
Zn1 N10 C14 C17 -178.6(14) 1_545 . . . ?
N10 C14 N11 C15 -174(2) . . . . ?
C17 C14 N11 C15 10(4) . . . . ?
C14 N11 C15 N12 -10(4) . . . . ?
N11 C15 N12 C16 3(4) . . . . ?
C15 N12 C16 C17 5(4) . . . . ?
C15 N12 C16 S3 173(2) . . . . ?
C13 N9 C17 C16 180(3) . . . . ?
Zn2 N9 C17 C16 8(4) . . . . ?
C13 N9 C17 C14 3(3) . . . . ?
Zn2 N9 C17 C14 -168.9(13) . . . . ?
N12 C16 C17 N9 178(2) . . . . ?
S3 C16 C17 N9 10(4) . . . . ?
N12 C16 C17 C14 -5(3) . . . . ?
S3 C16 C17 C14 -173.0(17) . . . . ?
N11 C14 C17 N9 175(2) . . . . ?
N10 C14 C17 N9 -2(3) . . . . ?
N11 C14 C17 C16 -3(4) . . . . ?
N10 C14 C17 C16 -179.7(19) . . . . ?
N12 C16 S3 C18 18(2) . . . . ?
C17 C16 S3 C18 -174(2) . . . . ?
Zn1 O1 C19 N13 -175.0(13) . . . . ?
O1 C19 N13 C21 -5(3) . . . . ?
O1 C19 N13 C20 180(2) . . . . ?
Zn2 O3 N14 O4 -2.1(19) . . . . ?
Zn2 O3 N14 O5 178.7(15) . . . . ?

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
C6 H6C N11 0.96 2.62 3.46(3) 145.9 2_565
C13 H13 N3 0.93 2.38 3.25(3) 154.4 .
C1 H1 N11 0.93 2.39 3.24(3) 151.8 1_565
C7 H7 O1 0.93 2.37 2.97(2) 121.8 2_474
C7 H7 O3 0.93 2.47 2.99(2) 115.5 .
C9 H9 O4 0.93 2.57 3.49(2) 170.2 1_455
C21 H21A O1 0.96 2.32 2.71(3) 103.0 .

_refine_diff_density_max         0.770
_refine_diff_density_min         -0.398
_refine_diff_density_rms         0.093

_shelxl_version_number           2014/6



# start Validation Reply Form
_vrf_PLAT316_shelx               
;
PROBLEM: Too many H on C in C=N Moiety in Main Residue .. C21 Check
RESPONSE: The N13-C21 distance is shorter than that expected for a sp3 
hybridization of C21. This is due to an electron dislocation in ligand DMF. 
Chemically, the C20 and C21 atoms must be equal, thus both were refined by 
means of AFIX 137. (It was attempted to locate the hydrogen atoms of these 
carbons in electron density maps, but data were not good enough.)
;
# end Validation Reply Form
