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

#######################################################################
#
#                 Cambridge Crystallographic Data Centre
#                                CCDC 
# 
#######################################################################
# 
#  This CIF contains data from an original supplementary publication
#  deposited with the CCDC, and may include chemical, crystal,
#  experimental, refinement, atomic coordinates,
#  anisotropic displacement parameters and molecular geometry data,
#  as required by the journal to which it was submitted.
#
#  This CIF is provided on the understanding that it is used for bona
#  fide research purposes only. It may contain copyright material
#  of the CCDC or of third parties, and may not be copied or further
#  disseminated in any form, whether machine-readable or not,
#  except for the purpose of generating routine backup copies
#  on your local computer system.
# 
#  For further information on the CCDC, data deposition and
#  data retrieval see:
#                         www.ccdc.cam.ac.uk
#
#  Bona fide researchers may freely download Mercury and enCIFer
#  from this site to visualise CIF-encoded structures and 
#  to carry out CIF format checking respectively.
#
data_13410b

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C20 H16 N12 O5 S Zn2'
_chemical_formula_weight         667.25

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'
S S 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_symmetry_cell_setting           Monoclinic
_symmetry_space_group_name_H-M   P2(1)/c

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

_cell_length_a                   11.7747(5)
_cell_length_b                   15.2659(5)
_cell_length_c                   14.3648(6)
_cell_angle_alpha                90.00
_cell_angle_beta                 108.979(4)
_cell_angle_gamma                90.00
_cell_volume                     2441.72(17)
_cell_formula_units_Z            4
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    4879
_cell_measurement_theta_min      3.7270
_cell_measurement_theta_max      28.8310

_exptl_crystal_description       block
_exptl_crystal_colour            colorless
_exptl_crystal_size_max          0.28
_exptl_crystal_size_mid          0.22
_exptl_crystal_size_min          0.18
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.815
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1344
_exptl_absorpt_coefficient_mu    2.112
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.78353
_exptl_absorpt_correction_T_max  1.00000
_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)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      293(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'SuperNova (Mo) X-ray Source'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, Atlas'
_diffrn_measurement_method       'ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            8307
_diffrn_reflns_av_R_equivalents  0.0254
_diffrn_reflns_av_unetI/netI     0.0394
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       -18
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_theta_min         3.00
_diffrn_reflns_theta_max         25.01
_reflns_number_total             4269
_reflns_number_gt                3768
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'CrysAlisPro, Oxford Diffraction Ltd.'
_computing_cell_refinement       'CrysAlisPro, Oxford Diffraction Ltd.'
_computing_data_reduction        'CrysAlisPro, Oxford Diffraction Ltd.'
_computing_structure_solution    'SHELXS97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 2008)'
_computing_molecular_graphics    'SHELXTL (Sheldrick, 1997)'
_computing_publication_material  'SHELXTL (Sheldrick, 1997)'

_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)+(0.0318P)²+1.3997P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    none
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         4269
_refine_ls_number_parameters     377
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0351
_refine_ls_R_factor_gt           0.0293
_refine_ls_wR_factor_ref         0.0741
_refine_ls_wR_factor_gt          0.0706
_refine_ls_goodness_of_fit_ref   1.042
_refine_ls_restrained_S_all      1.042
_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 0.57440(3) 0.23213(2) 0.62099(2) 0.01207(10) Uani 1 1 d . . .
Zn2 Zn 0.42966(3) 0.19860(2) 0.36866(2) 0.01116(10) Uani 1 1 d . . .
S1 S 0.48097(6) 0.13290(4) 0.76018(5) 0.01287(16) Uani 1 1 d . . .
N1 N 0.4420(2) 0.30663(14) 0.54368(15) 0.0142(5) Uani 1 1 d . . .
N12 N 1.29124(19) -0.20781(14) 0.77632(15) 0.0122(5) Uani 1 1 d . . .
N2 N 0.3707(2) 0.27665(15) 0.45335(16) 0.0152(5) Uani 1 1 d . . .
N7 N 0.64389(19) 0.17000(15) 0.52943(15) 0.0136(5) Uani 1 1 d . . .
O1 O 0.48698(18) 0.22892(12) 0.78031(14) 0.0217(5) Uani 1 1 d . . .
N8 N 0.57073(19) 0.13136(14) 0.44516(14) 0.0129(5) Uani 1 1 d . . .
O2 O 0.53360(17) 0.12315(12) 0.67933(14) 0.0207(4) Uani 1 1 d . . .
N9 N 0.9309(2) -0.02002(14) 0.58770(15) 0.0140(5) Uani 1 1 d . . .
C10 C -0.1479(2) 0.52682(17) 0.29551(19) 0.0144(6) Uani 1 1 d . . .
H10 H -0.1304 0.4674 0.2963 0.017 Uiso 1 1 calc R . .
N6 N -0.28639(19) 0.64318(15) 0.23096(15) 0.0124(5) Uani 1 1 d . . .
C19 C 1.2586(2) -0.12503(18) 0.78614(19) 0.0158(6) Uani 1 1 d . . .
H19 H 1.3051 -0.0926 0.8398 0.019 Uiso 1 1 calc R . .
C1 C 0.3927(2) 0.38021(18) 0.56337(19) 0.0163(6) Uani 1 1 d . . .
H1 H 0.4237 0.4137 0.6200 0.020 Uiso 1 1 calc R . .
C18 C 1.2237(2) -0.25352(19) 0.69767(19) 0.0180(6) Uani 1 1 d . . .
H18 H 1.2465 -0.3105 0.6894 0.022 Uiso 1 1 calc R . .
C11 C 0.7449(2) 0.12357(18) 0.56052(18) 0.0147(6) Uani 1 1 d . . .
H11 H 0.8093 0.1359 0.6168 0.018 Uiso 1 1 calc R . .
C8 C -0.2076(2) 0.69878(18) 0.29342(19) 0.0164(6) Uani 1 1 d . . .
H8 H -0.2291 0.7573 0.2940 0.020 Uiso 1 1 calc R . .
C4 C 0.2049(2) 0.47173(17) 0.47187(18) 0.0119(6) Uani 1 1 d . . .
C9 C -0.2559(2) 0.55840(18) 0.23376(18) 0.0139(6) Uani 1 1 d . . .
H9A H -0.3097 0.5193 0.1924 0.017 Uiso 1 1 calc R . .
N5 N 0.09415(19) 0.47185(14) 0.40744(15) 0.0121(5) Uani 1 1 d . . .
N3 N 0.2278(2) 0.54928(15) 0.51773(16) 0.0150(5) Uani 1 1 d . . .
C14 C 0.8302(2) -0.01406(17) 0.51174(19) 0.0134(6) Uani 1 1 d . . .
N11 N 0.9130(2) -0.14012(15) 0.49108(15) 0.0166(5) Uani 1 1 d . . .
N10 N 0.8188(2) -0.08470(15) 0.45338(17) 0.0166(5) Uani 1 1 d . . .
C13 C 0.6292(2) 0.06262(18) 0.42515(19) 0.0159(6) Uani 1 1 d . . .
H13 H 0.5996 0.0259 0.3710 0.019 Uiso 1 1 calc R . .
N4 N 0.13126(19) 0.60367(15) 0.48403(15) 0.0149(5) Uani 1 1 d . . .
C2 C 0.2884(2) 0.39919(18) 0.48680(18) 0.0130(6) Uani 1 1 d . . .
C5 C 0.0533(2) 0.55398(17) 0.41721(18) 0.0132(6) Uani 1 1 d . . .
C20 C 1.1592(2) -0.08595(19) 0.72009(18) 0.0176(6) Uani 1 1 d . . .
H20 H 1.1404 -0.0279 0.7282 0.021 Uiso 1 1 calc R . .
C12 C 0.7405(2) 0.05438(18) 0.49731(18) 0.0133(6) Uani 1 1 d . . .
C16 C 1.0874(2) -0.13514(18) 0.64075(18) 0.0134(6) Uani 1 1 d . . .
C6 C -0.0654(2) 0.58452(18) 0.35662(18) 0.0125(6) Uani 1 1 d . . .
C7 C -0.0980(2) 0.67253(18) 0.35554(19) 0.0155(6) Uani 1 1 d . . .
H7 H -0.0460 0.7128 0.3965 0.019 Uiso 1 1 calc R . .
C17 C 1.1234(2) -0.22033(18) 0.62953(19) 0.0171(6) Uani 1 1 d . . .
H17 H 1.0795 -0.2542 0.5761 0.021 Uiso 1 1 calc R . .
C15 C 0.9774(2) -0.09824(18) 0.57198(18) 0.0146(6) Uani 1 1 d . . .
C3 C 0.2792(2) 0.33190(18) 0.42014(19) 0.0167(6) Uani 1 1 d . . .
H3 H 0.2176 0.3262 0.3604 0.020 Uiso 1 1 calc R . .
O3 O 0.55231(18) 0.08503(14) 0.84587(15) 0.0302(5) Uani 1 1 d . . .
O5 O 0.02318(19) 0.36649(14) 0.22623(17) 0.0258(5) Uani 1 1 d . . .
O4 O 0.35661(16) 0.10330(13) 0.72774(13) 0.0189(4) Uani 1 1 d . . .
H5B H 0.039(3) 0.395(3) 0.286(3) 0.051(11) Uiso 1 1 d . . .
H5A H 0.011(4) 0.408(3) 0.176(3) 0.085(16) Uiso 1 1 d . . .
H3A H 0.296(3) 0.568(2) 0.564(2) 0.023(8) Uiso 1 1 d . . .
H10A H 0.762(3) -0.100(2) 0.392(2) 0.039(10) Uiso 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 N1 1.958(2) . ?
Zn1 O2 1.9907(19) . ?
Zn1 N7 2.000(2) . ?
Zn1 N12 2.000(2) 2_756 ?
Zn2 N8 1.958(2) . ?
Zn2 O1 1.9615(19) 4_565 ?
Zn2 N2 1.983(2) . ?
Zn2 N6 2.010(2) 2_545 ?
S1 O3 1.443(2) . ?
S1 O4 1.4565(19) . ?
S1 O2 1.4910(19) . ?
S1 O1 1.4913(19) . ?
N1 C1 1.336(3) . ?
N1 N2 1.374(3) . ?
N12 C19 1.341(3) . ?
N12 C18 1.346(3) . ?
N12 Zn1 2.000(2) 2_746 ?
N2 C3 1.329(3) . ?
N7 C11 1.331(3) . ?
N7 N8 1.370(3) . ?
O1 Zn2 1.9615(19) 4_566 ?
N8 C13 1.336(3) . ?
N9 C14 1.328(3) . ?
N9 C15 1.362(3) . ?
C10 C9 1.379(4) . ?
C10 C6 1.391(4) . ?
C10 H10 0.9300 . ?
N6 C9 1.340(3) . ?
N6 C8 1.358(3) . ?
N6 Zn2 2.010(2) 2 ?
C19 C20 1.380(4) . ?
C19 H19 0.9300 . ?
C1 C2 1.387(4) . ?
C1 H1 0.9300 . ?
C18 C17 1.363(4) . ?
C18 H18 0.9300 . ?
C11 C12 1.383(4) . ?
C11 H11 0.9300 . ?
C8 C7 1.369(4) . ?
C8 H8 0.9300 . ?
C4 N5 1.331(3) . ?
C4 N3 1.339(3) . ?
C4 C2 1.450(4) . ?
C9 H9A 0.9300 . ?
N5 C5 1.366(3) . ?
N3 N4 1.363(3) . ?
N3 H3A 0.90(3) . ?
C14 N10 1.345(3) . ?
C14 C12 1.452(4) . ?
N11 C15 1.327(3) . ?
N11 N10 1.360(3) . ?
N10 H10A 0.95(3) . ?
C13 C12 1.388(4) . ?
C13 H13 0.9300 . ?
N4 C5 1.329(3) . ?
C2 C3 1.384(4) . ?
C5 C6 1.462(4) . ?
C20 C16 1.397(4) . ?
C20 H20 0.9300 . ?
C16 C17 1.393(4) . ?
C16 C15 1.462(4) . ?
C6 C7 1.396(4) . ?
C7 H7 0.9300 . ?
C17 H17 0.9300 . ?
C3 H3 0.9300 . ?
O5 H5B 0.93(4) . ?
O5 H5A 0.94(5) . ?

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 Zn1 O2 117.88(9) . . ?
N1 Zn1 N7 108.86(9) . . ?
O2 Zn1 N7 94.98(8) . . ?
N1 Zn1 N12 116.43(9) . 2_756 ?
O2 Zn1 N12 108.29(8) . 2_756 ?
N7 Zn1 N12 107.92(9) . 2_756 ?
N8 Zn2 O1 104.55(9) . 4_565 ?
N8 Zn2 N2 111.91(9) . . ?
O1 Zn2 N2 108.72(9) 4_565 . ?
N8 Zn2 N6 122.78(9) . 2_545 ?
O1 Zn2 N6 99.35(8) 4_565 2_545 ?
N2 Zn2 N6 108.03(9) . 2_545 ?
O3 S1 O4 111.20(12) . . ?
O3 S1 O2 109.86(12) . . ?
O4 S1 O2 110.44(11) . . ?
O3 S1 O1 110.77(13) . . ?
O4 S1 O1 110.26(11) . . ?
O2 S1 O1 104.10(11) . . ?
C1 N1 N2 107.8(2) . . ?
C1 N1 Zn1 133.55(18) . . ?
N2 N1 Zn1 118.12(16) . . ?
C19 N12 C18 117.7(2) . . ?
C19 N12 Zn1 122.62(18) . 2_746 ?
C18 N12 Zn1 119.41(18) . 2_746 ?
C3 N2 N1 107.6(2) . . ?
C3 N2 Zn2 124.48(18) . . ?
N1 N2 Zn2 123.45(16) . . ?
C11 N7 N8 107.7(2) . . ?
C11 N7 Zn1 122.97(17) . . ?
N8 N7 Zn1 120.74(16) . . ?
S1 O1 Zn2 132.48(12) . 4_566 ?
C13 N8 N7 108.0(2) . . ?
C13 N8 Zn2 133.88(17) . . ?
N7 N8 Zn2 116.43(16) . . ?
S1 O2 Zn1 117.57(11) . . ?
C14 N9 C15 102.9(2) . . ?
C9 C10 C6 119.5(2) . . ?
C9 C10 H10 120.2 . . ?
C6 C10 H10 120.2 . . ?
C9 N6 C8 117.7(2) . . ?
C9 N6 Zn2 125.63(18) . 2 ?
C8 N6 Zn2 116.23(18) . 2 ?
N12 C19 C20 122.9(2) . . ?
N12 C19 H19 118.6 . . ?
C20 C19 H19 118.6 . . ?
N1 C1 C2 110.0(2) . . ?
N1 C1 H1 125.0 . . ?
C2 C1 H1 125.0 . . ?
N12 C18 C17 123.2(3) . . ?
N12 C18 H18 118.4 . . ?
C17 C18 H18 118.4 . . ?
N7 C11 C12 110.4(2) . . ?
N7 C11 H11 124.8 . . ?
C12 C11 H11 124.8 . . ?
N6 C8 C7 123.0(3) . . ?
N6 C8 H8 118.5 . . ?
C7 C8 H8 118.5 . . ?
N5 C4 N3 109.6(2) . . ?
N5 C4 C2 124.6(2) . . ?
N3 C4 C2 125.7(2) . . ?
N6 C9 C10 122.6(2) . . ?
N6 C9 H9A 118.7 . . ?
C10 C9 H9A 118.7 . . ?
C4 N5 C5 103.2(2) . . ?
C4 N3 N4 110.6(2) . . ?
C4 N3 H3A 129(2) . . ?
N4 N3 H3A 120(2) . . ?
N9 C14 N10 109.8(2) . . ?
N9 C14 C12 125.5(2) . . ?
N10 C14 C12 124.5(2) . . ?
C15 N11 N10 102.1(2) . . ?
C14 N10 N11 110.3(2) . . ?
C14 N10 H10A 132(2) . . ?
N11 N10 H10A 117(2) . . ?
N8 C13 C12 109.8(2) . . ?
N8 C13 H13 125.1 . . ?
C12 C13 H13 125.1 . . ?
C5 N4 N3 102.1(2) . . ?
C3 C2 C1 104.1(2) . . ?
C3 C2 C4 124.6(2) . . ?
C1 C2 C4 131.3(2) . . ?
N4 C5 N5 114.5(2) . . ?
N4 C5 C6 123.4(2) . . ?
N5 C5 C6 122.1(2) . . ?
C19 C20 C16 118.8(3) . . ?
C19 C20 H20 120.6 . . ?
C16 C20 H20 120.6 . . ?
C11 C12 C13 104.2(2) . . ?
C11 C12 C14 125.9(2) . . ?
C13 C12 C14 129.7(3) . . ?
C17 C16 C20 118.0(2) . . ?
C17 C16 C15 121.2(2) . . ?
C20 C16 C15 120.8(2) . . ?
C10 C6 C7 118.0(2) . . ?
C10 C6 C5 120.7(2) . . ?
C7 C6 C5 121.3(2) . . ?
C8 C7 C6 119.1(3) . . ?
C8 C7 H7 120.4 . . ?
C6 C7 H7 120.4 . . ?
C18 C17 C16 119.3(3) . . ?
C18 C17 H17 120.4 . . ?
C16 C17 H17 120.4 . . ?
N11 C15 N9 114.9(2) . . ?
N11 C15 C16 122.3(2) . . ?
N9 C15 C16 122.7(2) . . ?
N2 C3 C2 110.5(2) . . ?
N2 C3 H3 124.7 . . ?
C2 C3 H3 124.7 . . ?
H5B O5 H5A 110(4) . . ?

_diffrn_measured_fraction_theta_max 0.993
_diffrn_reflns_theta_full        25.01
_diffrn_measured_fraction_theta_full 0.993
_refine_diff_density_max         0.457
_refine_diff_density_min         -0.371
_refine_diff_density_rms         0.076
_database_code_depnum_ccdc_archive 'CCDC 984658'
#######################################################################
#
#                 Cambridge Crystallographic Data Centre
#                                CCDC 
# 
#######################################################################
# 
#  This CIF contains data from an original supplementary publication
#  deposited with the CCDC, and may include chemical, crystal,
#  experimental, refinement, atomic coordinates,
#  anisotropic displacement parameters and molecular geometry data,
#  as required by the journal to which it was submitted.
#
#  This CIF is provided on the understanding that it is used for bona
#  fide research purposes only. It may contain copyright material
#  of the CCDC or of third parties, and may not be copied or further
#  disseminated in any form, whether machine-readable or not,
#  except for the purpose of generating routine backup copies
#  on your local computer system.
# 
#  For further information on the CCDC, data deposition and
#  data retrieval see:
#                         www.ccdc.cam.ac.uk
#
#  Bona fide researchers may freely download Mercury and enCIFer
#  from this site to visualise CIF-encoded structures and 
#  to carry out CIF format checking respectively.
#
data_z03-2

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C20 H14 N12 O Zn2'
_chemical_formula_weight         569.17

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

_symmetry_cell_setting           Monoclinic
_symmetry_space_group_name_H-M   P21/c

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

_cell_length_a                   7.2259(2)
_cell_length_b                   18.6983(6)
_cell_length_c                   15.1420(6)
_cell_angle_alpha                90.00
_cell_angle_beta                 93.144(3)
_cell_angle_gamma                90.00
_cell_volume                     2042.80(13)
_cell_formula_units_Z            2
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    8036
_cell_measurement_theta_min      3.3580
_cell_measurement_theta_max      28.4850

_exptl_crystal_description       block
_exptl_crystal_colour            colorless
_exptl_crystal_size_max          0.32
_exptl_crystal_size_mid          0.28
_exptl_crystal_size_min          0.20
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    0.925
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             572
_exptl_absorpt_coefficient_mu    1.197
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.82049
_exptl_absorpt_correction_T_max  1.00000
_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)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      293(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'SuperNova (Mo) X-ray Source'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'SuperNova, Single source at offset, Eos'
_diffrn_measurement_method       'ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            15368
_diffrn_reflns_av_R_equivalents  0.0351
_diffrn_reflns_av_unetI/netI     0.0302
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_k_min       -22
_diffrn_reflns_limit_k_max       22
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_theta_min         3.03
_diffrn_reflns_theta_max         25.02
_reflns_number_total             3605
_reflns_number_gt                3182
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'CrysAlisPro, Oxford Diffraction Ltd.'
_computing_cell_refinement       'CrysAlisPro, Oxford Diffraction Ltd.'
_computing_data_reduction        'CrysAlisPro, Oxford Diffraction Ltd.'
_computing_structure_solution    'SHELXS97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 2008)'
_computing_molecular_graphics    'SHELXTL (Sheldrick, 1997)'
_computing_publication_material  'SHELXTL (Sheldrick, 1997)'

_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)+(0.0957P)²+0.9486P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    none
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         3605
_refine_ls_number_parameters     172
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0465
_refine_ls_R_factor_gt           0.0419
_refine_ls_wR_factor_ref         0.1479
_refine_ls_wR_factor_gt          0.1444
_refine_ls_goodness_of_fit_ref   1.091
_refine_ls_restrained_S_all      1.091
_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 0.36247(4) 0.579672(17) 0.48077(2) 0.02738(18) Uani 1 1 d . . .
N6 N -0.3725(3) 0.92961(13) 0.9558(2) 0.0312(6) Uani 1 1 d . . .
N5 N -0.2803(3) 0.99328(14) 0.95656(17) 0.0293(6) Uani 1 1 d . . .
N1 N 0.3204(4) 0.66093(15) 0.5675(2) 0.0387(7) Uani 1 1 d . . .
C8 C -0.1081(4) 0.91325(17) 0.8897(2) 0.0324(7) Uani 1 1 d . . .
C10 C -0.1221(4) 0.98346(18) 0.9171(2) 0.0329(7) Uani 1 1 d . . .
H10 H -0.0338 1.0187 0.9091 0.039 Uiso 1 1 calc R . .
N3 N 0.2232(3) 0.88536(15) 0.87211(18) 0.0351(6) Uani 1 1 d . . .
N2 N 0.3226(3) 0.84339(16) 0.8182(2) 0.0406(7) Uani 1 1 d . . .
N4 N 0.0186(4) 0.83319(16) 0.7782(2) 0.0453(8) Uani 1 1 d . . .
C3 C 0.2400(4) 0.7617(2) 0.6953(3) 0.0435(9) Uani 1 1 d . . .
C7 C 0.0439(4) 0.87808(17) 0.8459(2) 0.0343(7) Uani 1 1 d . . .
C5 C 0.1521(5) 0.6890(3) 0.5719(3) 0.0659(13) Uani 1 1 d . . .
H5 H 0.0597 0.6744 0.5305 0.079 Uiso 1 1 calc R . .
C9 C -0.2702(4) 0.88220(18) 0.9150(2) 0.0395(8) Uani 1 1 d . . .
H9 H -0.3031 0.8347 0.9050 0.047 Uiso 1 1 calc R . .
C6 C 0.1963(4) 0.81378(19) 0.7640(2) 0.0410(8) Uani 1 1 d . . .
C4 C 0.1076(5) 0.7385(3) 0.6346(3) 0.0679(14) Uani 1 1 d . . .
H4 H -0.0126 0.7561 0.6354 0.081 Uiso 1 1 calc R . .
C1 C 0.4496(5) 0.6842(3) 0.6265(3) 0.0655(13) Uani 1 1 d . . .
H1 H 0.5689 0.6658 0.6246 0.079 Uiso 1 1 calc R . .
C2 C 0.4154(5) 0.7340(3) 0.6900(3) 0.0706(15) Uani 1 1 d . . .
H2 H 0.5107 0.7490 0.7294 0.085 Uiso 1 1 calc R . .
O1 O 0.8157(15) 0.7996(5) 0.3233(8) 0.067(4) Uani 0.25 1 d PG . .
H1A H 0.8565 0.8417 0.3162 0.100 Uiso 0.25 1 d PG . .
H1B H 0.8449 0.7734 0.2802 0.100 Uiso 0.25 1 d PG . .
O2 O 0.827(2) 0.5791(6) 0.7088(8) 0.082(5) Uani 0.25 1 d PG . .
H2A H 0.7449 0.5690 0.7447 0.122 Uiso 0.25 1 d PG . .
H2B H 0.8419 0.6242 0.7070 0.122 Uiso 0.25 1 d PG . .


_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 N6 1.980(3) 4_675 ?
Zn1 N5 1.981(2) 2_546 ?
Zn1 N3 1.991(3) 4_575 ?
Zn1 N1 2.042(3) . ?
N6 C9 1.328(4) . ?
N6 N5 1.364(3) . ?
N6 Zn1 1.980(2) 4_476 ?
N5 C10 1.332(4) . ?
N5 Zn1 1.981(2) 2_556 ?
N1 C5 1.330(5) . ?
N1 C1 1.329(5) . ?
C8 C9 1.380(5) . ?
C8 C10 1.382(4) . ?
C8 C7 1.469(4) . ?
C10 H10 0.9300 . ?
N3 C7 1.341(4) . ?
N3 N2 1.365(4) . ?
N3 Zn1 1.991(3) 4_576 ?
N2 C6 1.315(4) . ?
N4 C7 1.330(4) . ?
N4 C6 1.362(4) . ?
C3 C4 1.361(5) . ?
C3 C2 1.376(5) . ?
C3 C6 1.472(5) . ?
C5 C4 1.377(6) . ?
C5 H5 0.9300 . ?
C9 H9 0.9300 . ?
C4 H4 0.9300 . ?
C1 C2 1.371(5) . ?
C1 H1 0.9300 . ?
C2 H2 0.9300 . ?
O1 H1A 0.8497 . ?
O1 H1B 0.8501 . ?
O2 H2A 0.8501 . ?
O2 H2B 0.8499 . ?

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
N6 Zn1 N5 109.78(10) 4_675 2_546 ?
N6 Zn1 N3 108.74(11) 4_675 4_575 ?
N5 Zn1 N3 120.82(11) 2_546 4_575 ?
N6 Zn1 N1 111.59(11) 4_675 . ?
N5 Zn1 N1 103.86(12) 2_546 . ?
N3 Zn1 N1 101.58(12) 4_575 . ?
C9 N6 N5 107.6(2) . . ?
C9 N6 Zn1 126.8(2) . 4_476 ?
N5 N6 Zn1 123.50(18) . 4_476 ?
C10 N5 N6 107.9(2) . . ?
C10 N5 Zn1 127.9(2) . 2_556 ?
N6 N5 Zn1 123.84(18) . 2_556 ?
C5 N1 C1 116.6(3) . . ?
C5 N1 Zn1 119.7(3) . . ?
C1 N1 Zn1 123.5(2) . . ?
C9 C8 C10 103.9(3) . . ?
C9 C8 C7 127.1(3) . . ?
C10 C8 C7 129.0(3) . . ?
N5 C10 C8 110.1(3) . . ?
N5 C10 H10 124.9 . . ?
C8 C10 H10 124.9 . . ?
C7 N3 N2 107.2(3) . . ?
C7 N3 Zn1 135.6(2) . 4_576 ?
N2 N3 Zn1 115.11(19) . 4_576 ?
C6 N2 N3 104.2(2) . . ?
C7 N4 C6 101.5(3) . . ?
C4 C3 C2 117.1(3) . . ?
C4 C3 C6 121.2(3) . . ?
C2 C3 C6 121.7(3) . . ?
N4 C7 N3 112.4(3) . . ?
N4 C7 C8 123.8(3) . . ?
N3 C7 C8 123.7(3) . . ?
N1 C5 C4 123.3(4) . . ?
N1 C5 H5 118.4 . . ?
C4 C5 H5 118.4 . . ?
N6 C9 C8 110.5(3) . . ?
N6 C9 H9 124.7 . . ?
C8 C9 H9 124.7 . . ?
N2 C6 N4 114.7(3) . . ?
N2 C6 C3 123.4(3) . . ?
N4 C6 C3 121.9(3) . . ?
C3 C4 C5 119.9(3) . . ?
C3 C4 H4 120.0 . . ?
C5 C4 H4 120.0 . . ?
N1 C1 C2 123.1(3) . . ?
N1 C1 H1 118.4 . . ?
C2 C1 H1 118.4 . . ?
C1 C2 C3 120.0(4) . . ?
C1 C2 H2 120.0 . . ?
C3 C2 H2 120.0 . . ?
H1A O1 H1B 109.4 . . ?
H2A O2 H2B 109.5 . . ?

loop_
_platon_squeeze_void_nr
_platon_squeeze_void_average_x
_platon_squeeze_void_average_y
_platon_squeeze_void_average_z
_platon_squeeze_void_volume
_platon_squeeze_void_count_electrons
_platon_squeeze_void_content
1 -0.067 0.500 0.000 463 56 ' '
2 0.004 0.000 0.500 463 57 ' '
_platon_squeeze_details          
;
;

_diffrn_measured_fraction_theta_max 0.998
_diffrn_reflns_theta_full        25.02
_diffrn_measured_fraction_theta_full 0.998
_refine_diff_density_max         0.695
_refine_diff_density_min         -0.303
_refine_diff_density_rms         0.090

#===END
_database_code_depnum_ccdc_archive 'CCDC 984659'
