# Electronic Supplementary Material (ESI) for CrystEngComm.
# This journal is © The Royal Society of Chemistry 2014

####################################################################### 
# 
# 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 have may 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_ic14870
_database_code_depnum_ccdc_archive 'CCDC 1015113'
_audit_update_record             
;
2014-10-29 deposited with the CCDC.
2014-11-20 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C18.62 H18.47 N2 O6.62 S2 Zn'
_chemical_formula_weight         505.67

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

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

_cell_length_a                   9.4960(11)
_cell_length_b                   11.5347(13)
_cell_length_c                   11.8048(13)
_cell_angle_alpha                67.494(2)
_cell_angle_beta                 81.395(2)
_cell_angle_gamma                69.474(2)
_cell_volume                     1118.5(2)
_cell_formula_units_Z            2
_cell_measurement_temperature    150(2)
_cell_measurement_reflns_used    2886
_cell_measurement_theta_min      2.29
_cell_measurement_theta_max      25.00

_exptl_crystal_description       plate
_exptl_crystal_colour            colorless
_exptl_crystal_size_max          0.50
_exptl_crystal_size_mid          0.30
_exptl_crystal_size_min          0.05
_exptl_crystal_density_meas      not_measured
_exptl_crystal_density_diffrn    1.501
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             518
_exptl_absorpt_coefficient_mu    1.324
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.5574
_exptl_absorpt_correction_T_max  0.9368
_exptl_absorpt_process_details   'SADABS (Bruker, 2001)'

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      150(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 SMART APEXCCD area detector'
_diffrn_measurement_method       'omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            13798
_diffrn_reflns_av_R_equivalents  0.0538
_diffrn_reflns_av_sigmaI/netI    0.0694
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_theta_min         1.87
_diffrn_reflns_theta_max         27.50
_reflns_number_total             5117
_reflns_number_gt                4088
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'Bruker SMART'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_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)+(0.1009P)²+3.4829P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         5117
_refine_ls_number_parameters     270
_refine_ls_number_restraints     7
_refine_ls_R_factor_all          0.0873
_refine_ls_R_factor_gt           0.0713
_refine_ls_wR_factor_ref         0.2036
_refine_ls_wR_factor_gt          0.1923
_refine_ls_goodness_of_fit_ref   1.038
_refine_ls_restrained_S_all      1.041
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
Zn1 Zn -0.55076(6) 1.20314(5) 1.27838(5) 0.02613(19) Uani 1 1 d . . .
S1 S -0.77066(19) 0.69881(16) 1.34192(15) 0.0462(4) Uani 1 1 d . . .
S2 S -0.5763(2) 0.56276(15) 1.31492(16) 0.0556(5) Uani 1 1 d . . .
O1 O -0.3546(4) 1.0949(4) 1.3542(4) 0.0331(8) Uani 1 1 d . . .
O2 O -0.2925(4) 1.2780(4) 1.2999(4) 0.0370(9) Uani 1 1 d . . .
O3 O -0.6694(4) 1.2802(3) 1.3979(4) 0.0335(8) Uani 1 1 d . . .
O4 O -0.8315(4) 1.3786(5) 1.2474(4) 0.0426(10) Uani 1 1 d . . .
N1 N -0.6207(4) 1.0486(4) 1.2933(4) 0.0246(8) Uani 1 1 d . . .
N2 N -0.4843(5) 0.7096(4) 0.9040(4) 0.0350(10) Uani 1 1 d . . .
C1 C -0.5421(5) 0.9255(5) 1.3645(5) 0.0291(10) Uani 1 1 d . . .
H1 H -0.4560 0.9138 1.4047 0.035 Uiso 1 1 calc R . .
C2 C -0.5815(6) 0.8150(5) 1.3815(5) 0.0331(11) Uani 1 1 d . . .
H2 H -0.5239 0.7291 1.4322 0.040 Uiso 1 1 calc R . .
C3 C -0.7078(6) 0.8337(5) 1.3223(5) 0.0302(11) Uani 1 1 d . . .
C4 C -0.7887(5) 0.9582(5) 1.2497(5) 0.0317(11) Uani 1 1 d . . .
H4 H -0.8747 0.9723 1.2079 0.038 Uiso 1 1 calc R . .
C5 C -0.7420(5) 1.0640(5) 1.2385(5) 0.0294(10) Uani 1 1 d . . .
H5 H -0.7993 1.1509 1.1896 0.035 Uiso 1 1 calc R . .
C6 C -0.6217(7) 0.7595(10) 0.9480(7) 0.071(3) Uani 1 1 d . . .
H6 H -0.6971 0.8245 0.8915 0.085 Uiso 1 1 calc R . .
C7 C -0.6581(8) 0.7210(10) 1.0701(7) 0.067(2) Uani 1 1 d . . .
H7 H -0.7559 0.7602 1.0980 0.081 Uiso 1 1 calc R . .
C8 C -0.5499(8) 0.6237(6) 1.1529(6) 0.0476(16) Uani 1 1 d . . .
C9 C -0.4104(10) 0.5747(7) 1.1086(7) 0.087(3) Uani 1 1 d . . .
H9 H -0.3322 0.5105 1.1627 0.104 Uiso 1 1 calc R . .
C10 C -0.3841(9) 0.6202(7) 0.9824(7) 0.073(3) Uani 1 1 d . . .
H10 H -0.2868 0.5834 0.9522 0.088 Uiso 1 1 calc R . .
C11 C -0.0895(5) 0.9374(5) 1.4792(4) 0.0254(9) Uani 1 1 d . . .
H11 H -0.1507 0.8949 1.4645 0.031 Uiso 1 1 calc R . .
C12 C -0.1280(5) 1.0754(5) 1.4297(4) 0.0250(9) Uani 1 1 d . . .
C13 C -0.0375(5) 1.1375(5) 1.4505(4) 0.0255(9) Uani 1 1 d . . .
H13 H -0.0632 1.2312 1.4163 0.031 Uiso 1 1 calc R . .
C14 C -0.2673(5) 1.1576(5) 1.3557(5) 0.0277(10) Uani 1 1 d . . .
C15 C -0.8636(5) 1.4091(5) 1.5464(5) 0.0303(10) Uani 1 1 d . . .
H15 H -0.7694 1.3467 1.5785 0.036 Uiso 1 1 calc R . .
C16 C -0.9022(5) 1.4302(5) 1.4299(4) 0.0253(9) Uani 1 1 d . . .
C17 C -1.0408(5) 1.5231(5) 1.3836(5) 0.0310(10) Uani 1 1 d . . .
H17 H -1.0689 1.5393 1.3037 0.037 Uiso 1 1 calc R . .
C18 C -0.7955(5) 1.3590(5) 1.3516(5) 0.0289(10) Uani 1 1 d . . .
O5 O -0.9297(6) 1.6366(7) 0.8522(5) 0.0808(19) Uani 1 1 d . . .
H5A H -0.9841 1.6169 0.8142 0.121 Uiso 1 1 d R . .
H5B H -0.8773 1.6806 0.7982 0.121 Uiso 1 1 d R . .
O6 O -0.9947(11) 1.6592(11) 1.0742(9) 0.155(4) Uani 1 1 d U . .
H6A H -0.9967 1.6424 1.0076 0.233 Uiso 1 1 d R . .
H6B H -0.9702 1.5857 1.1430 0.233 Uiso 1 1 d R . .
O7 O -1.063(2) 1.9233(18) 1.0740(16) 0.150 Uiso 0.616(12) 1 d PD . .
H7A H -1.0913 2.0039 1.0651 0.225 Uiso 0.616(12) 1 d PR . .
C19 C -1.185(3) 1.873(3) 1.095(2) 0.150 Uiso 0.616(12) 1 d PD . .
H19A H -1.2394 1.9077 1.0192 0.225 Uiso 0.616(12) 1 d PR . .
H19B H -1.2513 1.9050 1.1568 0.225 Uiso 0.616(12) 1 d PR . .
H19C H -1.1503 1.7764 1.1262 0.225 Uiso 0.616(12) 1 d PR . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Zn1 O3 1.958(4) . ?
Zn1 O1 1.960(3) . ?
Zn1 N2 2.030(5) 2_477 ?
Zn1 N1 2.051(4) . ?
S1 C3 1.779(5) . ?
S1 S2 2.036(2) . ?
S2 C8 1.780(6) . ?
O1 C14 1.283(6) . ?
O2 C14 1.238(6) . ?
O3 C18 1.269(6) . ?
O4 C18 1.241(6) . ?
N1 C5 1.329(6) . ?
N1 C1 1.346(6) . ?
N2 C10 1.293(9) . ?
N2 C6 1.342(8) . ?
N2 Zn1 2.030(5) 2_477 ?
C1 C2 1.385(7) . ?
C2 C3 1.388(7) . ?
C3 C4 1.367(8) . ?
C4 C5 1.394(7) . ?
C6 C7 1.366(10) . ?
C7 C8 1.386(11) . ?
C8 C9 1.356(10) . ?
C9 C10 1.393(10) . ?
C11 C13 1.383(7) 2_578 ?
C11 C12 1.397(7) . ?
C12 C13 1.393(6) . ?
C12 C14 1.498(7) . ?
C13 C11 1.383(7) 2_578 ?
C15 C17 1.376(7) 2_388 ?
C15 C16 1.384(7) . ?
C16 C17 1.398(7) . ?
C16 C18 1.508(7) . ?
C17 C15 1.376(7) 2_388 ?
O7 C19 1.409(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
O3 Zn1 O1 105.08(16) . . ?
O3 Zn1 N2 130.26(17) . 2_477 ?
O1 Zn1 N2 108.06(17) . 2_477 ?
O3 Zn1 N1 106.86(15) . . ?
O1 Zn1 N1 96.60(15) . . ?
N2 Zn1 N1 105.00(17) 2_477 . ?
C3 S1 S2 101.64(18) . . ?
C8 S2 S1 102.9(2) . . ?
C14 O1 Zn1 116.5(3) . . ?
C18 O3 Zn1 108.7(3) . . ?
C5 N1 C1 118.2(4) . . ?
C5 N1 Zn1 123.4(3) . . ?
C1 N1 Zn1 118.4(3) . . ?
C10 N2 C6 117.4(6) . . ?
C10 N2 Zn1 126.3(4) . 2_477 ?
C6 N2 Zn1 116.0(5) . 2_477 ?
N1 C1 C2 122.7(5) . . ?
C1 C2 C3 117.9(5) . . ?
C4 C3 C2 120.0(4) . . ?
C4 C3 S1 118.7(4) . . ?
C2 C3 S1 121.3(4) . . ?
C3 C4 C5 118.4(5) . . ?
N1 C5 C4 122.8(5) . . ?
N2 C6 C7 123.0(7) . . ?
C6 C7 C8 118.8(7) . . ?
C9 C8 C7 118.1(6) . . ?
C9 C8 S2 116.7(6) . . ?
C7 C8 S2 125.1(5) . . ?
C8 C9 C10 118.8(7) . . ?
N2 C10 C9 123.8(6) . . ?
C13 C11 C12 120.0(4) 2_578 . ?
C13 C12 C11 119.9(4) . . ?
C13 C12 C14 119.5(4) . . ?
C11 C12 C14 120.5(4) . . ?
C11 C13 C12 120.0(4) 2_578 . ?
O2 C14 O1 123.8(5) . . ?
O2 C14 C12 120.6(4) . . ?
O1 C14 C12 115.6(4) . . ?
C17 C15 C16 121.1(4) 2_388 . ?
C15 C16 C17 118.7(4) . . ?
C15 C16 C18 121.1(4) . . ?
C17 C16 C18 120.1(4) . . ?
C15 C17 C16 120.2(5) 2_388 . ?
O4 C18 O3 123.0(5) . . ?
O4 C18 C16 120.5(4) . . ?
O3 C18 C16 116.5(5) . . ?

_diffrn_measured_fraction_theta_max 0.998
_diffrn_reflns_theta_full        27.50
_diffrn_measured_fraction_theta_full 0.998
_refine_diff_density_max         1.761
_refine_diff_density_min         -0.759
_refine_diff_density_rms         0.137

_shelx_ins_file                  
;
TITL ic14870 in P-1
CELL 0.71073   9.4960  11.5347  11.8048  67.494  81.395  69.474
ZERR    2.00   0.0011   0.0013   0.0013   0.002   0.002   0.002
LATT 1
SFAC C  H  N  O  S  Zn
UNIT 37.24 36.94 4 13.24 4 2
OMIT  -3.00  55.00
L.S. 15
ACTA
BOND
FMAP 2
DFIX 1.40 0.01 O7 C19
ISOR 0.01 O6
PLAN 20
SIZE 0.05 0.30 0.50
TEMP -123
WGHT    0.100900    3.482900
FVAR       0.57788   0.61613
ZN1   6   -0.550762    1.203135    1.278382    11.00000    0.01830    0.02304 =
         0.03842   -0.01280    0.00277   -0.00755
S1    5   -0.770659    0.698814    1.341923    11.00000    0.06044    0.04682 =
         0.05263   -0.02861    0.02639   -0.04123
S2    5   -0.576323    0.562756    1.314922    11.00000    0.08996    0.03033 =
         0.05143   -0.02018    0.03267   -0.03243
O1    4   -0.354611    1.094854    1.354249    11.00000    0.01733    0.03379 =
         0.05350   -0.01949    0.00095   -0.01061
O2    4   -0.292504    1.278024    1.299869    11.00000    0.02626    0.02974 =
         0.05053   -0.00554   -0.00525   -0.01174
O3    4   -0.669414    1.280205    1.397928    11.00000    0.02652    0.02535 =
         0.04725   -0.01579    0.00666   -0.00642
O4    4   -0.831524    1.378586    1.247397    11.00000    0.03131    0.06347 =
         0.04336   -0.03374    0.00907   -0.01497
N1    3   -0.620740    1.048566    1.293257    11.00000    0.01890    0.02126 =
         0.03305   -0.01030    0.00278   -0.00645
N2    3   -0.484341    0.709617    0.903961    11.00000    0.03581    0.03322 =
         0.04277   -0.01941    0.00863   -0.01621
C1    1   -0.542096    0.925456    1.364463    11.00000    0.02124    0.02704 =
         0.03805   -0.01116   -0.00024   -0.00726
AFIX  43
H1    2   -0.455984    0.913812    1.404685    11.00000   -1.20000
AFIX   0
C2    1   -0.581517    0.815000    1.381537    11.00000    0.03084    0.02189 =
         0.04245   -0.01036    0.00448   -0.00680
AFIX  43
H2    2   -0.523934    0.729120    1.432211    11.00000   -1.20000
AFIX   0
C3    1   -0.707778    0.833720    1.322295    11.00000    0.03127    0.03225 =
         0.03841   -0.02082    0.01543   -0.02092
C4    1   -0.788716    0.958200    1.249708    11.00000    0.02331    0.03813 =
         0.03817   -0.01658    0.00056   -0.01243
AFIX  43
H4    2   -0.874697    0.972251    1.207940    11.00000   -1.20000
AFIX   0
C5    1   -0.742001    1.064009    1.238479    11.00000    0.02290    0.02666 =
         0.03779   -0.01213   -0.00068   -0.00629
AFIX  43
H5    2   -0.799286    1.150906    1.189573    11.00000   -1.20000
AFIX   0
C6    1   -0.621717    0.759461    0.947966    11.00000    0.03221    0.13561 =
         0.05321   -0.04834    0.00671   -0.02429
AFIX  43
H6    2   -0.697088    0.824487    0.891517    11.00000   -1.20000
AFIX   0
C7    1   -0.658104    0.720994    1.070139    11.00000    0.03440    0.12757 =
         0.05324   -0.05013    0.01030   -0.02645
AFIX  43
H7    2   -0.755877    0.760212    1.097961    11.00000   -1.20000
AFIX   0
C8    1   -0.549852    0.623700    1.152858    11.00000    0.07623    0.03363 =
         0.04694   -0.02233    0.02977   -0.03760
C9    1   -0.410426    0.574672    1.108599    11.00000    0.08751    0.03876 =
         0.05864    0.01238    0.02905    0.02284
AFIX  43
H9    2   -0.332184    0.510458    1.162704    11.00000   -1.20000
AFIX   0
C10   1   -0.384059    0.620185    0.982388    11.00000    0.06360    0.03472 =
         0.05873    0.00670    0.02894    0.01999
AFIX  43
H10   2   -0.286804    0.583409    0.952186    11.00000   -1.20000
AFIX   0
C11   1   -0.089538    0.937368    1.479189    11.00000    0.02090    0.02988 =
         0.03111   -0.01484    0.00594   -0.01292
AFIX  43
H11   2   -0.150745    0.894928    1.464471    11.00000   -1.20000
AFIX   0
C12   1   -0.128024    1.075367    1.429737    11.00000    0.01682    0.02923 =
         0.02898   -0.01222    0.00653   -0.00834
C13   1   -0.037549    1.137454    1.450478    11.00000    0.01951    0.02293 =
         0.03337   -0.01087    0.00304   -0.00659
AFIX  43
H13   2   -0.063157    1.231218    1.416298    11.00000   -1.20000
AFIX   0
C14   1   -0.267303    1.157632    1.355664    11.00000    0.01886    0.03255 =
         0.03346   -0.01555    0.00764   -0.00956
C15   1   -0.863565    1.409079    1.546397    11.00000    0.02089    0.02878 =
         0.03505   -0.00967   -0.00501   -0.00068
AFIX  43
H15   2   -0.769412    1.346684    1.578535    11.00000   -1.20000
AFIX   0
C16   1   -0.902219    1.430206    1.429909    11.00000    0.02184    0.02388 =
         0.03302   -0.01165    0.00442   -0.01091
C17   1   -1.040758    1.523053    1.383635    11.00000    0.02687    0.03005 =
         0.03274   -0.01051   -0.00512   -0.00418
AFIX  47
H17   2   -1.068878    1.539306    1.303664    11.00000   -1.20000
AFIX   0
C18   1   -0.795463    1.358974    1.351626    11.00000    0.02281    0.02211 =
         0.04224   -0.01170    0.00526   -0.00997
O5    4   -0.929667    1.636618    0.852157    11.00000    0.04679    0.11184 =
         0.06145    0.00046   -0.00758   -0.03147
AFIX   3
H5A   2   -0.984087    1.616918    0.814167    11.00000   -1.50000
H5B   2   -0.877297    1.680608    0.798197    11.00000   -1.50000
AFIX   0
O6    4   -0.994707    1.659161    1.074234    11.00000    0.14855    0.18027 =
         0.11124   -0.05489    0.01410   -0.02700
AFIX   3
H6A   2   -0.996686    1.642410    1.007645    11.00000   -1.50000
H6B   2   -0.970176    1.585720    1.143005    11.00000   -1.50000
AFIX   0
O7    4   -1.063372    1.923295    1.074033    21.00000   10.15000
AFIX   3
H7A   2   -1.091253    2.003887    1.065144    21.00000   -1.50000
AFIX   0
C19   1   -1.184652    1.873447    1.095494    21.00000   10.15000
AFIX   3
H19A  2   -1.239372    1.907677    1.019223    21.00000   -1.50000
H19B  2   -1.251322    1.904986    1.156825    21.00000   -1.50000
H19C  2   -1.150331    1.776358    1.126204    21.00000   -1.50000
 
HKLF 4
 
REM  ic14870 in P-1
REM R1 =  0.0713 for   4088 Fo > 4sig(Fo)  and  0.0873 for all   5117 data
REM    270 parameters refined using      7 restraints
 
END  
     
WGHT      0.0999      3.5195 
REM Highest difference peak  1.761,  deepest hole -0.759,  1-sigma level  0.137
Q1    1  -0.5227  1.1861  1.3520  11.00000  0.05    1.76
Q2    1  -1.3951  1.9173  1.0699  11.00000  0.05    1.33
Q3    1  -0.5968  0.5823  1.2465  11.00000  0.05    1.25
Q4    1  -1.3402  1.8786  1.0997  11.00000  0.05    1.19
Q5    1  -1.0136  2.0265  1.0342  11.00000  0.05    1.13
Q6    1  -0.6010  0.6380  1.0842  11.00000  0.05    0.93
Q7    1  -0.5511  1.2193  1.1896  11.00000  0.05    0.87
Q8    1  -0.5914  1.2698  1.2637  11.00000  0.05    0.86
Q9    1  -1.1614  1.6775  1.0387  11.00000  0.05    0.80
Q10   1  -0.8031  0.7196  1.2738  11.00000  0.05    0.80
Q11   1  -0.9416  1.7370  0.9121  11.00000  0.05    0.79
Q12   1  -1.1396  1.9239  1.1684  11.00000  0.05    0.74
Q13   1  -0.5746  0.6814  0.9557  11.00000  0.05    0.68
Q14   1  -1.0420  1.8144  0.9857  11.00000  0.05    0.66
Q15   1  -1.0295  1.5588  1.0734  11.00000  0.05    0.56
Q16   1  -0.4253  0.6405  0.9182  11.00000  0.05    0.55
Q17   1  -0.4232  0.5780  1.0458  11.00000  0.05    0.54
Q18   1  -0.5038  0.5666  1.3158  11.00000  0.05    0.51
Q19   1  -0.8912  1.4260  1.4890  11.00000  0.05    0.47
Q20   1  -0.5070  0.7215  0.8391  11.00000  0.05    0.45
;
####################################################################### 
# 
# 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 have may 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_ht13509
_database_code_depnum_ccdc_archive 'CCDC 1015114'
_audit_update_record             
;
2014-10-29 deposited with the CCDC.
2014-11-20 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C18 H12 N2 O4 S2 Zn'
_chemical_formula_weight         449.79

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

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

_cell_length_a                   9.6705(5)
_cell_length_b                   11.6246(6)
_cell_length_c                   11.7082(6)
_cell_angle_alpha                66.363(1)
_cell_angle_beta                 82.283(1)
_cell_angle_gamma                68.217(1)
_cell_volume                     1119.5(1)
_cell_formula_units_Z            2
_cell_measurement_temperature    393(2)
_cell_measurement_reflns_used    ?
_cell_measurement_theta_min      ?
_cell_measurement_theta_max      ?

_exptl_crystal_description       block
_exptl_crystal_colour            colorless
_exptl_crystal_size_max          0.16
_exptl_crystal_size_mid          0.09
_exptl_crystal_size_min          0.05
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.334
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             456
_exptl_absorpt_coefficient_mu    1.306
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.8164
_exptl_absorpt_correction_T_max  0.9321
_exptl_absorpt_process_details   ?

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      393(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  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            12281
_diffrn_reflns_av_R_equivalents  0.0276
_diffrn_reflns_av_sigmaI/netI    0.0314
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_theta_min         1.90
_diffrn_reflns_theta_max         27.50
_reflns_number_total             4988
_reflns_number_gt                4209
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'Bruker SMART'
_computing_cell_refinement       'Bruker SMART'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_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)+(0.0705P)²+0.0339P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         4988
_refine_ls_number_parameters     245
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0444
_refine_ls_R_factor_gt           0.0383
_refine_ls_wR_factor_ref         0.1135
_refine_ls_wR_factor_gt          0.1070
_refine_ls_goodness_of_fit_ref   1.083
_refine_ls_restrained_S_all      1.083
_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
Zn1 Zn -0.55467(2) 1.20898(2) 1.27940(2) 0.04921(11) Uani 1 1 d . . .
S1 S -0.76000(9) 0.70255(8) 1.34099(7) 0.0800(2) Uani 1 1 d . . .
S2 S -0.56721(10) 0.55737(7) 1.32511(6) 0.0814(2) Uani 1 1 d . . .
O1 O -0.35472(16) 1.09283(16) 1.35112(16) 0.0630(4) Uani 1 1 d . . .
O2 O -0.3208(2) 1.28101(17) 1.31692(18) 0.0789(5) Uani 1 1 d . . .
O3 O -0.67421(18) 1.27880(17) 1.39964(17) 0.0693(4) Uani 1 1 d . . .
O4 O -0.8327(2) 1.3895(2) 1.24294(19) 0.0995(7) Uani 1 1 d . . .
N1 N -0.62029(19) 1.05376(18) 1.28818(16) 0.0533(4) Uani 1 1 d . . .
N2 N -0.4765(2) 0.7006(2) 0.90781(18) 0.0594(4) Uani 1 1 d . . .
C1 C -0.5355(3) 0.9279(2) 1.3535(2) 0.0620(5) Uani 1 1 d . . .
H1 H -0.4473 0.9139 1.3890 0.074 Uiso 1 1 calc R . .
C2 C -0.5705(3) 0.8179(2) 1.3713(2) 0.0672(6) Uani 1 1 d . . .
H2 H -0.5083 0.7321 1.4186 0.081 Uiso 1 1 calc R . .
C3 C -0.6996(3) 0.8371(2) 1.3180(2) 0.0573(5) Uani 1 1 d . . .
C4 C -0.7908(3) 0.9671(3) 1.2521(2) 0.0658(6) Uani 1 1 d . . .
H4 H -0.8800 0.9835 1.2166 0.079 Uiso 1 1 calc R . .
C5 C -0.7479(3) 1.0719(2) 1.2399(2) 0.0628(6) Uani 1 1 d . . .
H5 H -0.8104 1.1590 1.1962 0.075 Uiso 1 1 calc R . .
C6 C -0.6119(3) 0.7438(4) 0.9501(3) 0.1153(15) Uani 1 1 d . . .
H6 H -0.6880 0.8060 0.8927 0.138 Uiso 1 1 calc R . .
C7 C -0.6459(3) 0.7016(5) 1.0744(3) 0.1166(14) Uani 1 1 d . . .
H7 H -0.7436 0.7330 1.0991 0.140 Uiso 1 1 calc R . .
C8 C -0.5376(3) 0.6146(2) 1.1607(2) 0.0642(6) Uani 1 1 d . . .
C9 C -0.3987(3) 0.5675(3) 1.1187(2) 0.0837(8) Uani 1 1 d . . .
H9 H -0.3213 0.5052 1.1748 0.100 Uiso 1 1 calc R . .
C10 C -0.3725(3) 0.6122(2) 0.9925(2) 0.0757(7) Uani 1 1 d . . .
H10 H -0.2764 0.5783 0.9658 0.091 Uiso 1 1 calc R . .
C11 C -0.0871(2) 0.9364(2) 1.48409(18) 0.0494(4) Uani 1 1 d . . .
H11 H -0.1456 0.8934 1.4732 0.059 Uiso 1 1 calc R . .
C12 C -0.13312(19) 1.07560(18) 1.43088(17) 0.0441(4) Uani 1 1 d . . .
C13 C -0.0439(2) 1.13884(19) 1.44720(18) 0.0490(4) Uani 1 1 d . . .
H13 H -0.0728 1.2318 1.4117 0.059 Uiso 1 1 calc R . .
C14 C -0.2787(2) 1.1584(2) 1.36010(18) 0.0509(4) Uani 1 1 d . . .
C15 C -0.8674(3) 1.4011(3) 1.5499(2) 0.0694(6) Uani 1 1 d . . .
H15 H -0.7777 1.3338 1.5846 0.083 Uiso 1 1 calc R . .
C16 C -0.9035(2) 1.4340(2) 1.4277(2) 0.0533(5) Uani 1 1 d . . .
C17 C -1.0369(3) 1.5331(3) 1.3785(2) 0.0697(6) Uani 1 1 d . . .
H17 H -1.0633 1.5562 1.2966 0.084 Uiso 1 1 calc R . .
C18 C -0.7986(3) 1.3645(2) 1.3486(2) 0.0615(5) 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 O3 1.9390(16) . ?
Zn1 O1 1.9637(15) . ?
Zn1 N2 2.0518(19) 2_477 ?
Zn1 N1 2.0863(17) . ?
S1 C3 1.777(2) . ?
S1 S2 2.0449(11) . ?
S2 C8 1.788(2) . ?
O1 C14 1.278(3) . ?
O2 C14 1.224(3) . ?
O3 C18 1.274(3) . ?
O4 C18 1.214(3) . ?
N1 C5 1.337(3) . ?
N1 C1 1.334(3) . ?
N2 C6 1.323(3) . ?
N2 C10 1.317(3) . ?
N2 Zn1 2.0519(19) 2_477 ?
C1 C2 1.372(3) . ?
C2 C3 1.374(3) . ?
C3 C4 1.384(3) . ?
C4 C5 1.377(3) . ?
C6 C7 1.373(4) . ?
C7 C8 1.348(4) . ?
C8 C9 1.357(4) . ?
C9 C10 1.377(4) . ?
C11 C13 1.380(3) 2_578 ?
C11 C12 1.392(3) . ?
C12 C13 1.396(3) . ?
C12 C14 1.505(3) . ?
C13 C11 1.380(3) 2_578 ?
C15 C17 1.388(3) 2_388 ?
C15 C16 1.382(3) . ?
C16 C17 1.374(3) . ?
C16 C18 1.510(3) . ?
C17 C15 1.388(3) 2_388 ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
O3 Zn1 O1 109.02(7) . . ?
O3 Zn1 N2 132.03(7) . 2_477 ?
O1 Zn1 N2 105.38(7) . 2_477 ?
O3 Zn1 N1 106.14(7) . . ?
O1 Zn1 N1 95.45(7) . . ?
N2 Zn1 N1 102.72(7) 2_477 . ?
C3 S1 S2 102.73(8) . . ?
C8 S2 S1 102.85(10) . . ?
C14 O1 Zn1 112.69(13) . . ?
C18 O3 Zn1 108.95(15) . . ?
C5 N1 C1 117.1(2) . . ?
C5 N1 Zn1 124.26(15) . . ?
C1 N1 Zn1 118.47(14) . . ?
C6 N2 C10 116.1(2) . . ?
C6 N2 Zn1 117.03(18) . 2_477 ?
C10 N2 Zn1 126.53(16) . 2_477 ?
N1 C1 C2 123.9(2) . . ?
C1 C2 C3 118.6(2) . . ?
C2 C3 C4 118.4(2) . . ?
C2 C3 S1 122.35(19) . . ?
C4 C3 S1 119.10(17) . . ?
C5 C4 C3 119.2(2) . . ?
N1 C5 C4 122.7(2) . . ?
N2 C6 C7 123.4(3) . . ?
C8 C7 C6 120.0(3) . . ?
C7 C8 C9 117.2(2) . . ?
C7 C8 S2 124.0(2) . . ?
C9 C8 S2 118.7(2) . . ?
C8 C9 C10 119.8(3) . . ?
N2 C10 C9 123.3(2) . . ?
C13 C11 C12 120.94(18) 2_578 . ?
C13 C12 C11 118.96(17) . . ?
C13 C12 C14 119.79(17) . . ?
C11 C12 C14 121.22(17) . . ?
C11 C13 C12 120.09(18) 2_578 . ?
O2 C14 O1 123.25(19) . . ?
O2 C14 C12 120.91(19) . . ?
O1 C14 C12 115.82(18) . . ?
C17 C15 C16 120.9(2) 2_388 . ?
C17 C16 C15 118.6(2) . . ?
C17 C16 C18 120.2(2) . . ?
C15 C16 C18 121.1(2) . . ?
C16 C17 C15 120.5(2) . 2_388 ?
O4 C18 O3 122.7(2) . . ?
O4 C18 C16 121.2(2) . . ?
O3 C18 C16 116.1(2) . . ?

_diffrn_measured_fraction_theta_max 0.970
_diffrn_reflns_theta_full        27.50
_diffrn_measured_fraction_theta_full 0.970
_refine_diff_density_max         0.409
_refine_diff_density_min         -0.356
_refine_diff_density_rms         0.081
####################################################################### 
# 
# 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 have may 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_ic13509_ht_to_rt-1
_database_code_depnum_ccdc_archive 'CCDC 1015115'
_audit_update_record             
;
2014-10-29 deposited with the CCDC.
2014-11-20 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C18 H14.20 N2 O5.10 S2 Zn'
_chemical_formula_weight         469.60

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

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

_cell_length_a                   9.5666(4)
_cell_length_b                   11.5400(5)
_cell_length_c                   11.8627(5)
_cell_angle_alpha                67.610(1)
_cell_angle_beta                 80.961(1)
_cell_angle_gamma                68.932(1)
_cell_volume                     1129.64(8)
_cell_formula_units_Z            2
_cell_measurement_temperature    295(2)
_cell_measurement_reflns_used    ?
_cell_measurement_theta_min      ?
_cell_measurement_theta_max      ?

_exptl_crystal_description       block
_exptl_crystal_colour            colorless
_exptl_crystal_size_max          0.16
_exptl_crystal_size_mid          0.09
_exptl_crystal_size_min          0.05
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.381
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             478
_exptl_absorpt_coefficient_mu    1.300
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.8170
_exptl_absorpt_correction_T_max  0.9324
_exptl_absorpt_process_details   'SADABS (Bruker, 2001)'

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      295(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  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            12869
_diffrn_reflns_av_R_equivalents  0.0213
_diffrn_reflns_av_sigmaI/netI    0.0283
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_theta_min         1.86
_diffrn_reflns_theta_max         27.50
_reflns_number_total             5106
_reflns_number_gt                4655
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'Bruker SMART'
_computing_cell_refinement       'Bruker SMART'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_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)+(0.1181P)²+0.2341P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         5106
_refine_ls_number_parameters     255
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0491
_refine_ls_R_factor_gt           0.0463
_refine_ls_wR_factor_ref         0.1604
_refine_ls_wR_factor_gt          0.1579
_refine_ls_goodness_of_fit_ref   1.088
_refine_ls_restrained_S_all      1.106
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
Zn1 Zn -0.54615(3) 1.20320(3) 1.27849(3) 0.03536(14) Uani 1 1 d . . .
S1 S -0.76723(12) 0.70104(10) 1.34332(9) 0.0630(3) Uani 1 1 d . . .
S2 S -0.57601(14) 0.56376(9) 1.31278(8) 0.0650(3) Uani 1 1 d . . .
O1 O -0.3512(2) 1.0947(2) 1.3530(2) 0.0464(5) Uani 1 1 d . . .
O2 O -0.2919(3) 1.2770(2) 1.3000(2) 0.0592(6) Uani 1 1 d . . .
O3 O -0.6678(2) 1.2808(2) 1.3960(2) 0.0480(5) Uani 1 1 d . . .
O4 O -0.8297(3) 1.3771(3) 1.2490(2) 0.0639(6) Uani 1 1 d . . .
N1 N -0.6136(2) 1.0471(2) 1.2928(2) 0.0371(5) Uani 1 1 d . . .
N2 N -0.4879(3) 0.7103(2) 0.9023(2) 0.0437(5) Uani 1 1 d . . .
C1 C -0.5379(3) 0.9255(3) 1.3625(3) 0.0427(6) Uani 1 1 d . . .
H1 H -0.4536 0.9133 1.4011 0.051 Uiso 1 1 calc R . .
C2 C -0.5778(4) 0.8158(3) 1.3808(3) 0.0477(7) Uani 1 1 d . . .
H2 H -0.5226 0.7317 1.4309 0.057 Uiso 1 1 calc R . .
C3 C -0.7033(3) 0.8352(3) 1.3218(3) 0.0442(6) Uani 1 1 d . . .
C4 C -0.7834(4) 0.9608(3) 1.2503(3) 0.0495(7) Uani 1 1 d . . .
H4 H -0.8680 0.9756 1.2106 0.059 Uiso 1 1 calc R . .
C5 C -0.7365(3) 1.0647(3) 1.2384(3) 0.0472(6) Uani 1 1 d . . .
H5 H -0.7919 1.1502 1.1910 0.057 Uiso 1 1 calc R . .
C6 C -0.6240(4) 0.7588(5) 0.9489(4) 0.0784(13) Uani 1 1 d . . .
H6 H -0.6985 0.8227 0.8952 0.094 Uiso 1 1 calc R . .
C7 C -0.6596(4) 0.7198(6) 1.0705(4) 0.0800(13) Uani 1 1 d . . .
H7 H -0.7556 0.7569 1.0983 0.096 Uiso 1 1 calc R . .
C8 C -0.5510(4) 0.6244(3) 1.1517(3) 0.0514(7) Uani 1 1 d . . .
C9 C -0.4120(5) 0.5748(4) 1.1051(3) 0.0733(12) Uani 1 1 d . . .
H9 H -0.3360 0.5106 1.1572 0.088 Uiso 1 1 calc R . .
C10 C -0.3836(4) 0.6197(4) 0.9809(3) 0.0639(10) Uani 1 1 d . . .
H10 H -0.2878 0.5852 0.9513 0.077 Uiso 1 1 calc R . .
C11 C -0.0890(3) 0.9375(3) 1.4807(2) 0.0364(5) Uani 1 1 d . . .
H11 H -0.1485 0.8953 1.4681 0.044 Uiso 1 1 calc R . .
C12 C -0.1270(3) 1.0753(2) 1.4283(2) 0.0331(5) Uani 1 1 d . . .
C13 C -0.0367(3) 1.1366(3) 1.4487(2) 0.0366(5) Uani 1 1 d . . .
H13 H -0.0613 1.2283 1.4144 0.044 Uiso 1 1 calc R . .
C14 C -0.2656(3) 1.1569(3) 1.3548(2) 0.0388(5) Uani 1 1 d . . .
C15 C -0.8633(3) 1.4083(3) 1.5460(3) 0.0489(7) Uani 1 1 d . . .
H15 H -0.7720 1.3465 1.5778 0.059 Uiso 1 1 calc R . .
C16 C -0.9009(3) 1.4304(3) 1.4292(3) 0.0379(5) Uani 1 1 d . . .
C17 C -1.0397(3) 1.5228(3) 1.3857(3) 0.0495(7) Uani 1 1 d . . .
H17 H -1.0672 1.5380 1.3082 0.059 Uiso 1 1 calc RD . .
C18 C -0.7942(3) 1.3596(3) 1.3510(3) 0.0421(6) Uani 1 1 d . . .
O5 O -0.9368(6) 1.6372(5) 0.8563(5) 0.0879(19) Uiso 0.672(10) 1 d P . .
H5A H -0.9912 1.6175 0.8184 0.132 Uiso 0.672(10) 1 d PR . .
H5B H -0.8844 1.6812 0.8024 0.132 Uiso 0.672(10) 1 d PR . .
O6 O -0.9978(14) 1.6796(13) 1.0569(9) 0.146(6) Uiso 0.428(15) 1 d P . .
H6A H -0.9998 1.6628 0.9903 0.219 Uiso 0.428(15) 1 d PR . .
H6B H -0.9733 1.6061 1.1257 0.219 Uiso 0.428(15) 1 d PRD . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Zn1 O3 1.947(2) . ?
Zn1 O1 1.9555(19) . ?
Zn1 N2 2.021(2) 2_477 ?
Zn1 N1 2.064(2) . ?
S1 C3 1.780(3) . ?
S1 S2 2.0330(15) . ?
S2 C8 1.777(3) . ?
O1 C14 1.275(3) . ?
O2 C14 1.233(3) . ?
O3 C18 1.272(4) . ?
O4 C18 1.230(4) . ?
N1 C1 1.324(4) . ?
N1 C5 1.343(4) . ?
N2 C10 1.325(4) . ?
N2 C6 1.342(4) . ?
N2 Zn1 2.021(2) 2_477 ?
C1 C2 1.381(4) . ?
C2 C3 1.390(4) . ?
C3 C4 1.370(5) . ?
C4 C5 1.378(4) . ?
C6 C7 1.364(5) . ?
C7 C8 1.379(6) . ?
C8 C9 1.366(5) . ?
C9 C10 1.380(5) . ?
C11 C13 1.382(4) 2_578 ?
C11 C12 1.397(4) . ?
C12 C13 1.392(3) . ?
C12 C14 1.499(3) . ?
C13 C11 1.382(4) 2_578 ?
C15 C17 1.368(4) 2_388 ?
C15 C16 1.392(4) . ?
C16 C17 1.394(4) . ?
C16 C18 1.500(4) . ?
C17 C15 1.368(4) 2_388 ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
O3 Zn1 O1 106.05(10) . . ?
O3 Zn1 N2 129.92(10) . 2_477 ?
O1 Zn1 N2 108.28(10) . 2_477 ?
O3 Zn1 N1 106.65(9) . . ?
O1 Zn1 N1 96.30(9) . . ?
N2 Zn1 N1 104.59(9) 2_477 . ?
C3 S1 S2 101.78(11) . . ?
C8 S2 S1 103.44(13) . . ?
C14 O1 Zn1 116.44(18) . . ?
C18 O3 Zn1 109.86(19) . . ?
C1 N1 C5 118.2(2) . . ?
C1 N1 Zn1 119.26(18) . . ?
C5 N1 Zn1 122.4(2) . . ?
C10 N2 C6 116.9(3) . . ?
C10 N2 Zn1 125.7(2) . 2_477 ?
C6 N2 Zn1 117.0(2) . 2_477 ?
N1 C1 C2 123.3(3) . . ?
C1 C2 C3 117.8(3) . . ?
C4 C3 C2 119.5(3) . . ?
C4 C3 S1 119.3(2) . . ?
C2 C3 S1 121.2(2) . . ?
C3 C4 C5 118.8(3) . . ?
N1 C5 C4 122.4(3) . . ?
N2 C6 C7 123.8(4) . . ?
C6 C7 C8 118.9(4) . . ?
C9 C8 C7 117.6(3) . . ?
C9 C8 S2 117.2(3) . . ?
C7 C8 S2 125.2(3) . . ?
C8 C9 C10 120.3(3) . . ?
N2 C10 C9 122.4(3) . . ?
C13 C11 C12 120.3(2) 2_578 . ?
C13 C12 C11 119.0(2) . . ?
C13 C12 C14 120.3(2) . . ?
C11 C12 C14 120.7(2) . . ?
C11 C13 C12 120.7(2) 2_578 . ?
O2 C14 O1 123.5(3) . . ?
O2 C14 C12 120.4(2) . . ?
O1 C14 C12 116.1(2) . . ?
C17 C15 C16 120.2(3) 2_388 . ?
C15 C16 C17 117.9(3) . . ?
C15 C16 C18 121.2(3) . . ?
C17 C16 C18 120.9(3) . . ?
C15 C17 C16 121.8(3) 2_388 . ?
O4 C18 O3 122.5(3) . . ?
O4 C18 C16 120.8(3) . . ?
O3 C18 C16 116.7(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
O5 H5A O4 0.87 1.97 2.806(6) 159.2 2_387
O5 H5B O2 0.87 2.01 2.844(6) 160.4 2_487

_diffrn_measured_fraction_theta_max 0.984
_diffrn_reflns_theta_full        27.50
_diffrn_measured_fraction_theta_full 0.984
_refine_diff_density_max         1.123
_refine_diff_density_min         -0.402
_refine_diff_density_rms         0.119

