# Electronic Supplementary Material (ESI) for CrystEngComm.
# This journal is © The Royal Society of Chemistry 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_DG1
_database_code_depnum_ccdc_archive 'CCDC 1454891'
_audit_update_record             
;
2016-02-20 deposited with the CCDC.
2016-06-17 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
 ?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C28 H20 N8 O6 Zn'
_chemical_formula_weight         629.89

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Zn Zn 0.2839 1.4301 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_symmetry_cell_setting           Triclinic
_symmetry_space_group_name_H-M   P-1

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

_cell_length_a                   10.377(5)
_cell_length_b                   10.954(5)
_cell_length_c                   13.394(5)
_cell_angle_alpha                81.382(5)
_cell_angle_beta                 86.711(5)
_cell_angle_gamma                63.095(5)
_cell_volume                     1342.3(10)
_cell_formula_units_Z            2
_cell_measurement_temperature    298(2)
_cell_measurement_reflns_used    250
_cell_measurement_theta_min      2.1
_cell_measurement_theta_max      27.7

_exptl_crystal_description       Block
_exptl_crystal_colour            Red
_exptl_crystal_size_max          0.20
_exptl_crystal_size_mid          0.10
_exptl_crystal_size_min          0.10
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.558
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             644
_exptl_absorpt_coefficient_mu    0.975
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.8957
_exptl_absorpt_correction_T_max  0.9573
_exptl_absorpt_process_details   
;
'XPREP' - A PROGRAM DATA PREPARATION & RECIPROCAL 
SPACE EXPLORATION,
Bruker Analytical X-ray Systems, 1997
;


_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      298(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            22740
_diffrn_reflns_av_R_equivalents  0.0249
_diffrn_reflns_av_sigmaI/netI    0.0249
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_h_max       13
_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         2.11
_diffrn_reflns_theta_max         27.67
_reflns_number_total             6235
_reflns_number_gt                5464
_reflns_threshold_expression     >2σ(I)

_computing_data_collection       'SMART APEX II (Bruker,2010)'
_computing_cell_refinement       'SMART APEX II'
_computing_data_reduction        'SAINT (Bruker,2000)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_molecular_graphics    'Ortep-3v2 for windows (Farrugia, 1997)'
_computing_publication_material  'PLATON (Spek, 2008)'

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

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0582P)²+1.0719P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    noref
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         6235
_refine_ls_number_parameters     407
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0465
_refine_ls_R_factor_gt           0.0400
_refine_ls_wR_factor_ref         0.1123
_refine_ls_wR_factor_gt          0.1075
_refine_ls_goodness_of_fit_ref   1.042
_refine_ls_restrained_S_all      1.042
_refine_ls_shift/su_max          0.007
_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 0.5194(3) 0.1770(3) 0.64164(18) 0.0435(6) Uani 1 1 d . . .
H1 H 0.4908 0.1167 0.6187 0.052 Uiso 1 1 calc R . .
C2 C 0.5217(4) 0.1789(3) 0.74464(18) 0.0473(7) Uani 1 1 d . . .
H2 H 0.4950 0.1213 0.7899 0.057 Uiso 1 1 calc R . .
C3 C 0.5642(3) 0.2677(3) 0.77871(16) 0.0334(5) Uani 1 1 d . . .
C4 C 0.5984(3) 0.3543(2) 0.70922(17) 0.0348(5) Uani 1 1 d . . .
H4 H 0.6247 0.4172 0.7302 0.042 Uiso 1 1 calc R . .
C5 C 0.5930(3) 0.3461(2) 0.60779(16) 0.0319(5) Uani 1 1 d . . .
H51 H 0.6160 0.4049 0.5610 0.038 Uiso 1 1 calc R . .
C6 C 0.5710(3) 0.1981(3) 1.04584(17) 0.0400(6) Uani 1 1 d . . .
C7 C 0.5831(11) 0.0862(10) 1.1143(7) 0.054(2) Uani 0.50 1 d P . 1
C8 C 0.5897(11) 0.0956(9) 1.2171(6) 0.052(2) Uani 0.50 1 d P . 1
C7A C 0.5137(9) 0.1246(10) 1.1161(7) 0.0400(18) Uani 0.50 1 d P . 2
C8A C 0.5164(8) 0.1351(9) 1.2178(6) 0.0386(16) Uani 0.50 1 d P . 2
C9 C 0.6011(4) 0.2969(3) 1.18209(19) 0.0505(7) Uani 1 1 d . . .
H9 H 0.6215 0.3629 1.2042 0.061 Uiso 1 1 calc R . .
C10 C 0.5985(4) 0.2954(3) 1.07963(19) 0.0538(8) Uani 1 1 d . . .
H10 H 0.6152 0.3597 1.0343 0.065 Uiso 1 1 calc R . .
C11 C 0.2867(2) 0.2991(2) 0.41300(16) 0.0301(5) Uani 1 1 d . . .
C12 C 0.1252(2) 0.3689(2) 0.39898(16) 0.0284(4) Uani 1 1 d . . .
C13 C 0.0552(3) 0.5095(2) 0.36258(18) 0.0333(5) Uani 1 1 d . . .
H13 H 0.1070 0.5607 0.3519 0.040 Uiso 1 1 calc R . .
C14 C -0.0928(3) 0.5731(2) 0.34227(19) 0.0366(5) Uani 1 1 d . . .
C15 C -0.1697(2) 0.4964(2) 0.35951(18) 0.0335(5) Uani 1 1 d . . .
H15 H -0.2684 0.5390 0.3458 0.040 Uiso 1 1 calc R . .
C16 C -0.1005(2) 0.3565(2) 0.39707(16) 0.0276(4) Uani 1 1 d . . .
C17 C -0.1841(2) 0.2736(2) 0.41412(16) 0.0287(4) Uani 1 1 d . . .
C18 C 0.0472(2) 0.2935(2) 0.41675(16) 0.0291(4) Uani 1 1 d . . .
H18 H 0.0941 0.2000 0.4421 0.035 Uiso 1 1 calc R . .
C19 C 0.2053(5) 0.4633(5) 0.9304(3) 0.0771(11) Uani 1 1 d . . .
H19 H 0.2125 0.4940 0.8626 0.093 Uiso 1 1 calc R . .
C20 C 0.1790(4) 0.3497(4) 0.9524(3) 0.0661(9) Uani 1 1 d . . .
H20 H 0.1702 0.3045 0.9016 0.079 Uiso 1 1 calc R . .
C21 C 0.1662(4) 0.3056(4) 1.0524(2) 0.0544(7) Uani 1 1 d . . .
C22 C 0.1813(4) 0.3750(4) 1.1246(3) 0.0655(9) Uani 1 1 d . . .
H22 H 0.1732 0.3474 1.1928 0.079 Uiso 1 1 calc R . .
C23 C 0.2086(5) 0.4861(4) 1.0935(4) 0.0800(12) Uani 1 1 d . . .
H23 H 0.2192 0.5326 1.1426 0.096 Uiso 1 1 calc R . .
C24 C 0.0913(4) 0.0413(4) 1.1851(3) 0.0629(9) Uani 1 1 d . . .
C25 C 0.0709(8) -0.0282(7) 1.1141(3) 0.129(3) Uani 1 1 d . . .
H25 H 0.0888 -0.0093 1.0461 0.154 Uiso 1 1 calc R . .
C26 C 0.0237(8) -0.1259(7) 1.1464(4) 0.137(3) Uani 1 1 d . . .
H26 H 0.0068 -0.1704 1.0985 0.164 Uiso 1 1 calc R . .
C27 C 0.0344(4) -0.1031(3) 1.3087(3) 0.0575(8) Uani 1 1 d . . .
H27 H 0.0262 -0.1312 1.3768 0.069 Uiso 1 1 calc R . .
C28 C 0.0813(4) -0.0035(3) 1.2839(2) 0.0563(7) Uani 1 1 d . . .
H28 H 0.1059 0.0326 1.3342 0.068 Uiso 1 1 calc R . .
N1 N 0.5562(2) 0.2575(2) 0.57391(13) 0.0304(4) Uani 1 1 d . . .
N2 N 0.5726(3) 0.2791(2) 0.88280(14) 0.0404(5) Uani 1 1 d . . .
N3 N 0.5631(3) 0.1855(2) 0.94169(15) 0.0434(5) Uani 1 1 d . . .
N4 N 0.5765(3) 0.2105(2) 1.25078(14) 0.0396(5) Uani 1 1 d . . .
N5 N 0.2208(4) 0.5312(4) 0.9971(3) 0.0860(11) Uani 1 1 d . . .
N6 N 0.1326(3) 0.1907(3) 1.0734(2) 0.0627(7) Uani 1 1 d . . .
N7 N 0.1323(4) 0.1508(3) 1.1629(2) 0.0658(8) Uani 1 1 d . . .
N8 N 0.0007(4) -0.1602(3) 1.2433(2) 0.0728(9) Uani 1 1 d . . .
O1 O 0.35334(18) 0.17219(18) 0.44173(14) 0.0399(4) Uani 1 1 d . . .
O2 O 0.35231(18) 0.37277(19) 0.39128(13) 0.0380(4) Uani 1 1 d . . .
O1W O 0.70280(18) 0.03030(17) 0.44359(13) 0.0378(4) Uani 1 1 d . . .
H1WA H 0.6719 -0.0068 0.4936 0.057 Uiso 1 1 d R . .
H1WB H 0.7086 -0.0092 0.3920 0.057 Uiso 1 1 d R . .
O3 O -0.12280(19) 0.15227(18) 0.45511(16) 0.0452(4) Uani 1 1 d . . .
O4 O -0.31608(16) 0.33623(17) 0.38521(11) 0.0309(3) Uani 1 1 d . . .
O5 O -0.1665(2) 0.7090(2) 0.30387(19) 0.0596(6) Uani 1 1 d . . .
H5 H -0.1108 0.7440 0.2966 0.089 Uiso 1 1 calc R . .
Zn1 Zn 0.56232(3) 0.23707(3) 0.412413(17) 0.02639(9) Uani 1 1 d . . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
C1 N1 1.331(3) . ?
C1 C2 1.385(3) . ?
C2 C3 1.376(3) . ?
C3 C4 1.377(3) . ?
C3 N2 1.430(3) . ?
C4 C5 1.381(3) . ?
C5 N1 1.335(3) . ?
C6 C10 1.364(4) . ?
C6 C7 1.377(10) . ?
C6 C7A 1.424(10) . ?
C6 N3 1.433(3) . ?
C7 C8 1.403(13) . ?
C8 N4 1.347(9) . ?
C7A C8A 1.386(13) . ?
C8A N4 1.369(8) . ?
C9 N4 1.319(3) . ?
C9 C10 1.377(4) . ?
C11 O1 1.249(3) . ?
C11 O2 1.266(3) . ?
C11 C12 1.504(3) . ?
C12 C18 1.384(3) . ?
C12 C13 1.393(3) . ?
C13 C14 1.392(3) . ?
C14 O5 1.361(3) . ?
C14 C15 1.386(3) . ?
C15 C16 1.390(3) . ?
C16 C18 1.390(3) . ?
C16 C17 1.503(3) . ?
C17 O3 1.237(3) . ?
C17 O4 1.275(3) . ?
C19 N5 1.304(6) . ?
C19 C20 1.378(5) . ?
C20 C21 1.374(5) . ?
C21 C22 1.372(5) . ?
C21 N6 1.437(4) . ?
C22 C23 1.372(5) . ?
C23 N5 1.332(6) . ?
C24 C28 1.356(4) . ?
C24 C25 1.384(6) . ?
C24 N7 1.432(4) . ?
C25 C26 1.373(6) . ?
C26 N8 1.334(5) . ?
C27 N8 1.295(5) . ?
C27 C28 1.376(5) . ?
N1 Zn1 2.2021(19) . ?
N2 N3 1.234(3) . ?
N4 Zn1 2.215(2) 1_556 ?
N6 N7 1.212(4) . ?
O2 Zn1 2.0130(19) . ?
O1W Zn1 2.0561(18) . ?
O4 Zn1 1.9935(17) 1_455 ?
Zn1 O4 1.9935(17) 1_655 ?
Zn1 N4 2.215(2) 1_554 ?

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 122.9(2) . . ?
C3 C2 C1 118.6(2) . . ?
C2 C3 C4 118.9(2) . . ?
C2 C3 N2 124.3(2) . . ?
C4 C3 N2 116.7(2) . . ?
C3 C4 C5 118.8(2) . . ?
N1 C5 C4 122.9(2) . . ?
C10 C6 C7 117.7(5) . . ?
C10 C6 C7A 117.5(4) . . ?
C7 C6 C7A 26.8(4) . . ?
C10 C6 N3 124.8(2) . . ?
C7 C6 N3 115.9(5) . . ?
C7A C6 N3 116.0(4) . . ?
C6 C7 C8 117.4(8) . . ?
N4 C8 C7 123.0(7) . . ?
C8A C7A C6 118.4(8) . . ?
N4 C8A C7A 121.2(7) . . ?
N4 C9 C10 124.0(2) . . ?
C6 C10 C9 118.8(2) . . ?
O1 C11 O2 121.6(2) . . ?
O1 C11 C12 120.8(2) . . ?
O2 C11 C12 117.6(2) . . ?
C18 C12 C13 120.0(2) . . ?
C18 C12 C11 120.7(2) . . ?
C13 C12 C11 119.2(2) . . ?
C14 C13 C12 119.8(2) . . ?
O5 C14 C15 117.7(2) . . ?
O5 C14 C13 122.5(2) . . ?
C15 C14 C13 119.8(2) . . ?
C14 C15 C16 120.6(2) . . ?
C18 C16 C15 119.3(2) . . ?
C18 C16 C17 120.3(2) . . ?
C15 C16 C17 120.3(2) . . ?
O3 C17 O4 124.7(2) . . ?
O3 C17 C16 119.0(2) . . ?
O4 C17 C16 116.3(2) . . ?
C12 C18 C16 120.5(2) . . ?
N5 C19 C20 125.1(4) . . ?
C21 C20 C19 117.4(4) . . ?
C22 C21 C20 119.0(3) . . ?
C22 C21 N6 124.4(3) . . ?
C20 C21 N6 116.5(3) . . ?
C21 C22 C23 118.3(4) . . ?
N5 C23 C22 123.9(4) . . ?
C28 C24 C25 117.7(3) . . ?
C28 C24 N7 117.0(3) . . ?
C25 C24 N7 125.1(3) . . ?
C26 C25 C24 118.3(4) . . ?
N8 C26 C25 123.3(4) . . ?
N8 C27 C28 124.3(3) . . ?
C24 C28 C27 119.0(3) . . ?
C1 N1 C5 117.80(19) . . ?
C1 N1 Zn1 120.11(16) . . ?
C5 N1 Zn1 122.05(15) . . ?
N3 N2 C3 113.8(2) . . ?
N2 N3 C6 113.5(2) . . ?
C9 N4 C8 114.4(4) . . ?
C9 N4 C8A 117.0(4) . . ?
C8 N4 C8A 29.2(4) . . ?
C9 N4 Zn1 120.36(17) . 1_556 ?
C8 N4 Zn1 124.0(4) . 1_556 ?
C8A N4 Zn1 119.5(3) . 1_556 ?
C19 N5 C23 116.3(3) . . ?
N7 N6 C21 113.3(3) . . ?
N6 N7 C24 113.9(3) . . ?
C27 N8 C26 116.7(3) . . ?
C11 O2 Zn1 103.91(15) . . ?
C17 O4 Zn1 118.75(15) . 1_455 ?
O4 Zn1 O2 109.76(8) 1_655 . ?
O4 Zn1 O1W 106.42(8) 1_655 . ?
O2 Zn1 O1W 143.67(7) . . ?
O4 Zn1 N1 90.42(7) 1_655 . ?
O2 Zn1 N1 92.60(7) . . ?
O1W Zn1 N1 90.30(7) . . ?
O4 Zn1 N4 89.12(7) 1_655 1_554 ?
O2 Zn1 N4 89.43(8) . 1_554 ?
O1W Zn1 N4 87.91(8) . 1_554 ?
N1 Zn1 N4 177.95(8) . 1_554 ?

_diffrn_measured_fraction_theta_max 0.992
_diffrn_reflns_theta_full        27.67
_diffrn_measured_fraction_theta_full 0.992
_refine_diff_density_max         0.898
_refine_diff_density_min         -1.021
_refine_diff_density_rms         0.068
####################################################################### 
# 
# 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_DG2
_database_code_depnum_ccdc_archive 'CCDC 1454892'
_audit_update_record             
;
2016-02-20 deposited with the CCDC.
2016-06-17 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
 ?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C15 H15 N2 O7 Zn'
_chemical_formula_weight         400.66

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Zn Zn 0.2839 1.4301 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_symmetry_cell_setting           Triclinic

_symmetry_space_group_name_H-M   P-1

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

_cell_length_a                   8.03660(10)
_cell_length_b                   9.3162(2)
_cell_length_c                   12.3132(2)
_cell_angle_alpha                97.7150(10)
_cell_angle_beta                 108.1040(10)
_cell_angle_gamma                113.1750(10)
_cell_volume                     770.05(2)
_cell_formula_units_Z            2
_cell_measurement_temperature    298(2)
_cell_measurement_reflns_used    250
_cell_measurement_theta_min      1.8
_cell_measurement_theta_max      27.6

_exptl_crystal_description       Block
_exptl_crystal_colour            Orange
_exptl_crystal_size_max          0.20
_exptl_crystal_size_mid          0.10
_exptl_crystal_size_min          0.10
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.728
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             410
_exptl_absorpt_coefficient_mu    1.638
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.8689
_exptl_absorpt_correction_T_max  0.9567
_exptl_absorpt_process_details   
;
'XPREP' - A PROGRAM DATA PREPARATION & RECIPROCAL 
SPACE EXPLORATION,
Bruker Analytical X-ray Systems, 1997
;

_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      298(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            13132
_diffrn_reflns_av_R_equivalents  0.0210
_diffrn_reflns_av_sigmaI/netI    0.0197
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_theta_min         1.82
_diffrn_reflns_theta_max         27.62
_reflns_number_total             3565
_reflns_number_gt                3182
_reflns_threshold_expression     >2σ(I)

_computing_data_collection       'SMART APEX II (Bruker,2010)'
_computing_cell_refinement       'SMART APEX II'
_computing_data_reduction        'SAINT (Bruker,2000)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_molecular_graphics    'Ortep-3v2 for windows (Farrugia, 1997)'
_computing_publication_material  'PLATON (Spek, 2008)'

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

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0679P)²+0.5170P] 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         3565
_refine_ls_number_parameters     229
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0421
_refine_ls_R_factor_gt           0.0377
_refine_ls_wR_factor_ref         0.1124
_refine_ls_wR_factor_gt          0.1092
_refine_ls_goodness_of_fit_ref   1.075
_refine_ls_restrained_S_all      1.075
_refine_ls_shift/su_max          0.007
_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(4) 0.5715(3) 0.3166(2) 0.0354(5) Uani 1 1 d . . .
H1 H 0.3817 0.5171 0.3660 0.042 Uiso 1 1 calc R . .
C1S C 0.9226(16) 0.8794(16) 0.7110(12) 0.214(6) Uani 1 1 d . . .
H1S1 H 1.0443 0.9454 0.7035 0.257 Uiso 1 1 calc R . .
H1S2 H 0.9364 0.7839 0.7251 0.257 Uiso 1 1 calc R . .
C2 C 0.3976(4) 0.4812(3) 0.2064(2) 0.0383(6) Uani 1 1 d . . .
H2 H 0.3217 0.3683 0.1808 0.046 Uiso 1 1 calc R . .
C2S C 1.0000(12) 0.9694(12) 0.8463(6) 0.156(4) Uani 1 1 d . . .
H1S3 H 1.1337 0.9895 0.8866 0.235 Uiso 1 1 calc R . .
H1S4 H 0.9187 0.9027 0.8811 0.235 Uiso 1 1 calc R . .
H1S5 H 0.9950 1.0714 0.8546 0.235 Uiso 1 1 calc R . .
C3 C 0.4782(4) 0.5619(3) 0.1349(2) 0.0359(5) Uani 1 1 d . . .
C4 C 0.5801(6) 0.7294(4) 0.1728(3) 0.0548(8) Uani 1 1 d . . .
H4 H 0.6315 0.7864 0.1249 0.066 Uiso 1 1 calc R . .
C5 C 0.6049(5) 0.8116(4) 0.2830(3) 0.0502(8) Uani 1 1 d . . .
H5 H 0.6728 0.9251 0.3081 0.060 Uiso 1 1 calc R . .
C6 C 0.3955(4) 0.7416(3) 0.6635(2) 0.0314(5) Uani 1 1 d . . .
C7 C 0.2455(3) 0.6201(3) 0.6971(2) 0.0255(4) Uani 1 1 d . . .
C8 C 0.2336(3) 0.6664(3) 0.8050(2) 0.0309(5) Uani 1 1 d . . .
H13 H 0.3144 0.7731 0.8545 0.037 Uiso 1 1 calc R . .
C9 C 0.1020(4) 0.5544(3) 0.8391(2) 0.0308(5) Uani 1 1 d . . .
C10 C -0.0208(3) 0.3956(3) 0.7649(2) 0.0278(5) Uani 1 1 d . . .
H15 H -0.1105 0.3205 0.7874 0.033 Uiso 1 1 calc R . .
C11 C -0.0086(3) 0.3497(3) 0.6564(2) 0.0240(4) Uani 1 1 d . . .
C12 C -0.1380(3) 0.1790(3) 0.5742(2) 0.0272(5) Uani 1 1 d . . .
C13 C 0.1249(3) 0.4614(3) 0.6225(2) 0.0252(4) Uani 1 1 d . . .
H18 H 0.1334 0.4301 0.5502 0.030 Uiso 1 1 calc R . .
N1 N 0.5351(3) 0.7341(3) 0.35495(19) 0.0325(4) Uani 1 1 d . . .
N2 N 0.4454(4) 0.4627(3) 0.0235(2) 0.0424(5) Uani 1 1 d . . .
O1 O 0.3953(2) 0.6939(2) 0.56224(16) 0.0332(4) Uani 1 1 d . . .
O1S O 0.8259(3) 0.8154(3) 0.6016(2) 0.0463(5) Uani 1 1 d . . .
O2 O 0.5141(4) 0.8785(3) 0.7343(2) 0.0626(7) Uani 1 1 d . . .
O1W O 0.7089(13) 1.0634(6) 0.9597(4) 0.191(3) Uani 1 1 d G . .
H2WA H 0.8120 1.0630 0.9551 0.287 Uiso 1 1 d G . .
H2WB H 0.6177 1.0265 0.8901 0.287 Uiso 1 1 d G . .
O3 O -0.0928(3) 0.1257(2) 0.49685(19) 0.0421(5) Uani 1 1 d . . .
O4 O -0.2952(2) 0.0931(2) 0.58959(17) 0.0321(4) Uani 1 1 d . . .
O5 O 0.0944(3) 0.6026(2) 0.94677(18) 0.0481(5) Uani 1 1 d . . .
H5A H 0.1748 0.6990 0.9802 0.072 Uiso 1 1 calc R . .
Zn1 Zn 0.58704(4) 0.85703(3) 0.52119(3) 0.03367(12) Uani 1 1 d . . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
C1 N1 1.335(3) . ?
C1 C2 1.379(4) . ?
C1S O1S 1.242(14) . ?
C1S C2S 1.561(14) . ?
C2 C3 1.381(4) . ?
C3 C4 1.373(4) . ?
C3 N2 1.431(3) . ?
C4 C5 1.378(4) . ?
C5 N1 1.336(4) . ?
C6 O2 1.234(3) . ?
C6 O1 1.266(3) . ?
C6 C7 1.506(3) . ?
C7 C8 1.384(3) . ?
C7 C13 1.387(3) . ?
C8 C9 1.382(3) . ?
C9 O5 1.369(3) . ?
C9 C10 1.387(3) . ?
C10 C11 1.392(3) . ?
C11 C13 1.387(3) . ?
C11 C12 1.499(3) . ?
C12 O3 1.231(3) . ?
C12 O4 1.291(3) . ?
N1 Zn1 2.034(2) . ?
N2 N2 1.238(5) 2_665 ?
O1 Zn1 1.9455(16) . ?
O1S Zn1 2.079(2) . ?
O4 Zn1 1.9519(17) 1_445 ?
Zn1 O4 1.9519(17) 1_665 ?

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) . . ?
O1S C1S C2S 165.5(9) . . ?
C1 C2 C3 118.7(3) . . ?
C4 C3 C2 119.0(2) . . ?
C4 C3 N2 124.2(3) . . ?
C2 C3 N2 116.7(2) . . ?
C3 C4 C5 119.0(3) . . ?
N1 C5 C4 122.3(3) . . ?
O2 C6 O1 123.0(2) . . ?
O2 C6 C7 120.3(2) . . ?
O1 C6 C7 116.7(2) . . ?
C8 C7 C13 120.2(2) . . ?
C8 C7 C6 119.5(2) . . ?
C13 C7 C6 120.2(2) . . ?
C9 C8 C7 120.2(2) . . ?
O5 C9 C8 119.1(2) . . ?
O5 C9 C10 120.7(2) . . ?
C8 C9 C10 120.2(2) . . ?
C9 C10 C11 119.4(2) . . ?
C13 C11 C10 120.5(2) . . ?
C13 C11 C12 118.6(2) . . ?
C10 C11 C12 120.88(19) . . ?
O3 C12 O4 122.7(2) . . ?
O3 C12 C11 120.5(2) . . ?
O4 C12 C11 116.8(2) . . ?
C11 C13 C7 119.5(2) . . ?
C1 N1 C5 118.5(2) . . ?
C1 N1 Zn1 119.76(18) . . ?
C5 N1 Zn1 121.74(18) . . ?
N2 N2 C3 113.1(3) 2_665 . ?
C6 O1 Zn1 115.10(15) . . ?
C1S O1S Zn1 118.0(5) . . ?
C12 O4 Zn1 115.77(15) . 1_445 ?
O1 Zn1 O4 125.35(7) . 1_665 ?
O1 Zn1 N1 102.40(8) . . ?
O4 Zn1 N1 127.26(8) 1_665 . ?
O1 Zn1 O1S 97.88(8) . . ?
O4 Zn1 O1S 100.80(9) 1_665 . ?
N1 Zn1 O1S 92.56(9) . . ?

_diffrn_measured_fraction_theta_max 0.996
_diffrn_reflns_theta_full        27.62
_diffrn_measured_fraction_theta_full 0.996
_refine_diff_density_max         0.739
_refine_diff_density_min         -0.737
_refine_diff_density_rms         0.088
