# Electronic Supplementary Material (ESI) for Chemical Science.
# 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_publication_text2

loop_
_audit_creation_method
SHELXL-97
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_formula_moiety         'C16 H15 N5 O2'
_chemical_formula_sum            'C16 H15 N5 O2'
_chemical_melting_point          ?

_exptl_crystal_description       needle
_exptl_crystal_colour            yellow

_diffrn_ambient_temperature      173(2)
_chemical_formula_weight         309.33

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'

_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_H-M   'P 21/c'
_symmetry_space_group_name_Hall  'P 2ybc'
_symmetry_int_tables_number      14
_chemical_absolute_configuration ?

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                   11.6410(8)
_cell_length_b                   8.7512(6)
_cell_length_c                   14.7356(10)
_cell_angle_alpha                90.00
_cell_angle_beta                 92.5980(10)
_cell_angle_gamma                90.00
_cell_volume                     1499.61(18)
_cell_formula_units_Z            4
_cell_measurement_temperature    173(2)
_cell_measurement_reflns_used    6231
_cell_measurement_theta_min      2.71
_cell_measurement_theta_max      25.28
_exptl_crystal_size_max          0.39
_exptl_crystal_size_mid          0.19
_exptl_crystal_size_min          0.16
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.370
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             648
_exptl_absorpt_coefficient_mu    0.095
_exptl_absorpt_correction_type   Multi-scan
_exptl_absorpt_correction_T_min  0.9635
_exptl_absorpt_correction_T_max  0.9853
_exptl_absorpt_process_details   SADABS
_exptl_special_details           
;
Data was collected using a BRUKER CCD (charge coupled device) based
diffractometer equipped with an Oxford low-temperature apparatus operating at
173 K. A suitable crystal was chosen and mounted on a glass fiber or nylon loop
using Paratone oil for Mo radiation and Mineral oil for Copper radiation. Data
were measured using omega and phi scans of 0.5° per frame
for 30 s. The total number of images were based on
results from the program COSMO where redundancy was expected to be 4 and
completeness to 0.83Å to 100%. Cell parameters were
retrieved using APEX II software and refined using SAINT on all observed
reflections.Data reduction was performed using the SAINT software which
corrects for Lp. Scaling and absorption corrections were applied using SADABS6
multi-scan technique, supplied by George Sheldrick. The structures are solved
by the direct method using the SHELXS-97 program and refined by least squares
method on F2, SHELXL-97, incorporated in SHELXTL-PC V 6.14.

All H atoms were placed in calculated positions and refined using a riding
model.
C-H(aromatic) = 0.94 Å and Uiso(H) = 1.2Ueq(C)
C-H (alaphatic) = 0.99 Å and Uiso(H) = 1.2Ueq(C)
CH2 = 0.98 Å and Uiso(H) = 1.2Ueq(C)
CH3 = 0.97Å and Uiso(H) = 1.5Ueq(C)
N-H = 0.86 (0.92)Å and Uiso(H) = 1.2 Ueq(N)
O-H(alcohol) = 0.85Åand Uiso(H) = 1.2Ueq(O)
O-H(acid) = 0.82Å and Uiso(H) = 1.5Ueq(O)
;
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'ω,and/f 0.5 deg'
_diffrn_detector_area_resol_mean 836.6
_diffrn_reflns_number            11726
_diffrn_reflns_av_R_equivalents  0.0292
_diffrn_reflns_av_sigmaI/netI    0.0225
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_theta_min         1.75
_diffrn_reflns_theta_max         25.34
_reflns_number_total             2739
_reflns_number_gt                2280
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'COSMO (BRUKER, V1.61, 2009)'
_computing_cell_refinement       'APEX2 (BRUKER, V2010.11-3, 2010)'
_computing_data_reduction        'SAINT (BRUKER, V7.68A, 2010)'
_computing_structure_solution    
'SHELXS (Sheldrick, Acta Cryst. A64 2008, 112-122)'
_computing_structure_refinement  
'SHELXL (Sheldrick, Acta Cryst. A64 2008, 112-122)'
_computing_molecular_graphics    
'SHELXTL (Sheldrick, Acta Cryst. A64 2008, 112-122)'
_computing_publication_material  
'SHELXTL (Sheldrick, Acta Cryst. A64 2008, 112-122)'

_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)+(0.0484P)²+0.9576P] 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         2739
_refine_ls_number_parameters     209
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0544
_refine_ls_R_factor_gt           0.0453
_refine_ls_wR_factor_ref         0.1191
_refine_ls_wR_factor_gt          0.1115
_refine_ls_goodness_of_fit_ref   1.072
_refine_ls_restrained_S_all      1.072
_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
O1 O 0.70735(11) 0.20053(17) 0.96405(9) 0.0396(4) Uani 1 1 d . . .
O2 O 0.51411(12) 0.20436(18) 0.95014(9) 0.0418(4) Uani 1 1 d . . .
N1 N 0.73591(12) -0.00733(17) 0.73023(9) 0.0258(3) Uani 1 1 d . . .
H1 H 0.6759 -0.0293 0.6941 0.031 Uiso 1 1 calc R . .
N2 N 0.72159(12) 0.05942(16) 0.81022(9) 0.0259(3) Uani 1 1 d . . .
N3 N 0.75464(13) -0.19456(17) 0.58721(10) 0.0283(4) Uani 1 1 d . . .
N4 N 0.41597(12) 0.16957(17) 0.77890(10) 0.0283(4) Uani 1 1 d . . .
H4A H 0.3974 0.2207 0.8276 0.034 Uiso 1 1 calc R . .
N5 N 0.51640(13) 0.03113(18) 0.68522(10) 0.0297(4) Uani 1 1 d . . .
C1 C 0.60625(15) 0.1736(2) 0.91988(12) 0.0292(4) Uani 1 1 d . . .
C2 C 0.61860(15) 0.1053(2) 0.82876(11) 0.0255(4) Uani 1 1 d . . .
C3 C 0.51778(15) 0.09884(19) 0.76637(11) 0.0254(4) Uani 1 1 d . . .
C4 C 0.34774(16) 0.1472(2) 0.70268(13) 0.0324(4) Uani 1 1 d . . .
H4 H 0.2716 0.1840 0.6915 0.039 Uiso 1 1 calc R . .
C5 C 0.41002(16) 0.0619(2) 0.64569(13) 0.0332(4) Uani 1 1 d . . .
H5 H 0.3837 0.0285 0.5870 0.040 Uiso 1 1 calc R . .
C6 C 0.70229(19) 0.2679(3) 1.05428(13) 0.0409(5) Uani 1 1 d . . .
H6A H 0.6364 0.3392 1.0556 0.049 Uiso 1 1 calc R . .
H6B H 0.7735 0.3265 1.0686 0.049 Uiso 1 1 calc R . .
C7 C 0.6894(3) 0.1475(3) 1.12244(15) 0.0665(8) Uani 1 1 d . . .
H7A H 0.6183 0.0906 1.1086 0.100 Uiso 1 1 calc R . .
H7B H 0.6863 0.1939 1.1828 0.100 Uiso 1 1 calc R . .
H7C H 0.7552 0.0777 1.1215 0.100 Uiso 1 1 calc R . .
C8 C 0.84630(15) -0.0421(2) 0.70405(11) 0.0256(4) Uani 1 1 d . . .
C9 C 0.94406(16) 0.0138(2) 0.74767(13) 0.0325(4) Uani 1 1 d . . .
H9 H 0.9386 0.0772 0.7996 0.039 Uiso 1 1 calc R . .
C10 C 1.05253(17) -0.0229(2) 0.71522(14) 0.0399(5) Uani 1 1 d . . .
H10 H 1.1198 0.0157 0.7462 0.048 Uiso 1 1 calc R . .
C11 C 1.06328(16) -0.1124(2) 0.64046(14) 0.0400(5) Uani 1 1 d . . .
H11 H 1.1374 -0.1343 0.6193 0.048 Uiso 1 1 calc R . .
C12 C 0.96453(15) -0.1724(2) 0.59454(12) 0.0311(4) Uani 1 1 d . . .
C13 C 0.96712(18) -0.2700(2) 0.51798(14) 0.0410(5) Uani 1 1 d . . .
H13 H 1.0387 -0.2969 0.4938 0.049 Uiso 1 1 calc R . .
C14 C 0.86784(18) -0.3253(2) 0.47903(13) 0.0405(5) Uani 1 1 d . . .
H14 H 0.8692 -0.3907 0.4277 0.049 Uiso 1 1 calc R . .
C15 C 0.76313(17) -0.2842(2) 0.51581(12) 0.0340(4) Uani 1 1 d . . .
H15 H 0.6942 -0.3232 0.4876 0.041 Uiso 1 1 calc R . .
C16 C 0.85423(15) -0.13864(19) 0.62664(11) 0.0253(4) 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
O1 C1 1.340(2) . ?
O1 C6 1.458(2) . ?
O2 C1 1.210(2) . ?
N1 N2 1.3328(19) . ?
N1 C8 1.392(2) . ?
N1 H1 0.8800 . ?
N2 C2 1.305(2) . ?
N3 C15 1.320(2) . ?
N3 C16 1.364(2) . ?
N4 C3 1.357(2) . ?
N4 C4 1.360(2) . ?
N4 H4A 0.8800 . ?
N5 C3 1.334(2) . ?
N5 C5 1.371(2) . ?
C1 C2 1.483(2) . ?
C2 C3 1.459(2) . ?
C4 C5 1.358(3) . ?
C4 H4 0.9500 . ?
C5 H5 0.9500 . ?
C6 C7 1.468(3) . ?
C6 H6A 0.9900 . ?
C6 H6B 0.9900 . ?
C7 H7A 0.9800 . ?
C7 H7B 0.9800 . ?
C7 H7C 0.9800 . ?
C8 C9 1.372(3) . ?
C8 C16 1.426(2) . ?
C9 C10 1.407(3) . ?
C9 H9 0.9500 . ?
C10 C11 1.362(3) . ?
C10 H10 0.9500 . ?
C11 C12 1.409(3) . ?
C11 H11 0.9500 . ?
C12 C13 1.417(3) . ?
C12 C16 1.419(2) . ?
C13 C14 1.356(3) . ?
C13 H13 0.9500 . ?
C14 C15 1.403(3) . ?
C14 H14 0.9500 . ?
C15 H15 0.9500 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C1 O1 C6 116.31(15) . . ?
N2 N1 C8 119.67(14) . . ?
N2 N1 H1 120.2 . . ?
C8 N1 H1 120.2 . . ?
C2 N2 N1 118.22(15) . . ?
C15 N3 C16 117.39(15) . . ?
C3 N4 C4 107.64(15) . . ?
C3 N4 H4A 126.2 . . ?
C4 N4 H4A 126.2 . . ?
C3 N5 C5 105.51(15) . . ?
O2 C1 O1 123.74(17) . . ?
O2 C1 C2 123.18(17) . . ?
O1 C1 C2 113.07(15) . . ?
N2 C2 C3 125.22(15) . . ?
N2 C2 C1 116.19(15) . . ?
C3 C2 C1 118.56(15) . . ?
N5 C3 N4 110.46(15) . . ?
N5 C3 C2 123.97(15) . . ?
N4 C3 C2 125.39(15) . . ?
C5 C4 N4 106.36(16) . . ?
C5 C4 H4 126.8 . . ?
N4 C4 H4 126.8 . . ?
C4 C5 N5 110.04(16) . . ?
C4 C5 H5 125.0 . . ?
N5 C5 H5 125.0 . . ?
O1 C6 C7 110.10(18) . . ?
O1 C6 H6A 109.6 . . ?
C7 C6 H6A 109.6 . . ?
O1 C6 H6B 109.6 . . ?
C7 C6 H6B 109.6 . . ?
H6A C6 H6B 108.2 . . ?
C6 C7 H7A 109.5 . . ?
C6 C7 H7B 109.5 . . ?
H7A C7 H7B 109.5 . . ?
C6 C7 H7C 109.5 . . ?
H7A C7 H7C 109.5 . . ?
H7B C7 H7C 109.5 . . ?
C9 C8 N1 123.28(16) . . ?
C9 C8 C16 120.26(16) . . ?
N1 C8 C16 116.45(15) . . ?
C8 C9 C10 119.83(18) . . ?
C8 C9 H9 120.1 . . ?
C10 C9 H9 120.1 . . ?
C11 C10 C9 121.52(18) . . ?
C11 C10 H10 119.2 . . ?
C9 C10 H10 119.2 . . ?
C10 C11 C12 120.00(17) . . ?
C10 C11 H11 120.0 . . ?
C12 C11 H11 120.0 . . ?
C11 C12 C13 124.12(17) . . ?
C11 C12 C16 119.55(17) . . ?
C13 C12 C16 116.30(17) . . ?
C14 C13 C12 120.24(17) . . ?
C14 C13 H13 119.9 . . ?
C12 C13 H13 119.9 . . ?
C13 C14 C15 118.94(18) . . ?
C13 C14 H14 120.5 . . ?
C15 C14 H14 120.5 . . ?
N3 C15 C14 123.92(19) . . ?
N3 C15 H15 118.0 . . ?
C14 C15 H15 118.0 . . ?
N3 C16 C12 123.21(16) . . ?
N3 C16 C8 117.96(15) . . ?
C12 C16 C8 118.83(16) . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C8 N1 N2 C2 172.85(15) . . . . ?
C6 O1 C1 O2 1.3(3) . . . . ?
C6 O1 C1 C2 179.96(16) . . . . ?
N1 N2 C2 C3 -4.3(3) . . . . ?
N1 N2 C2 C1 177.80(15) . . . . ?
O2 C1 C2 N2 -171.06(18) . . . . ?
O1 C1 C2 N2 10.3(2) . . . . ?
O2 C1 C2 C3 10.9(3) . . . . ?
O1 C1 C2 C3 -167.72(15) . . . . ?
C5 N5 C3 N4 0.4(2) . . . . ?
C5 N5 C3 C2 -174.95(16) . . . . ?
C4 N4 C3 N5 -0.6(2) . . . . ?
C4 N4 C3 C2 174.74(16) . . . . ?
N2 C2 C3 N5 6.8(3) . . . . ?
C1 C2 C3 N5 -175.33(16) . . . . ?
N2 C2 C3 N4 -167.86(17) . . . . ?
C1 C2 C3 N4 10.0(3) . . . . ?
C3 N4 C4 C5 0.4(2) . . . . ?
N4 C4 C5 N5 -0.2(2) . . . . ?
C3 N5 C5 C4 -0.1(2) . . . . ?
C1 O1 C6 C7 85.9(2) . . . . ?
N2 N1 C8 C9 -12.9(3) . . . . ?
N2 N1 C8 C16 168.38(15) . . . . ?
N1 C8 C9 C10 -177.98(17) . . . . ?
C16 C8 C9 C10 0.7(3) . . . . ?
C8 C9 C10 C11 0.5(3) . . . . ?
C9 C10 C11 C12 -1.0(3) . . . . ?
C10 C11 C12 C13 -178.1(2) . . . . ?
C10 C11 C12 C16 0.1(3) . . . . ?
C11 C12 C13 C14 178.6(2) . . . . ?
C16 C12 C13 C14 0.4(3) . . . . ?
C12 C13 C14 C15 0.0(3) . . . . ?
C16 N3 C15 C14 0.4(3) . . . . ?
C13 C14 C15 N3 -0.4(3) . . . . ?
C15 N3 C16 C12 0.0(3) . . . . ?
C15 N3 C16 C8 -179.77(16) . . . . ?
C11 C12 C16 N3 -178.68(17) . . . . ?
C13 C12 C16 N3 -0.4(3) . . . . ?
C11 C12 C16 C8 1.1(3) . . . . ?
C13 C12 C16 C8 179.41(17) . . . . ?
C9 C8 C16 N3 178.27(16) . . . . ?
N1 C8 C16 N3 -2.9(2) . . . . ?
C9 C8 C16 C12 -1.5(3) . . . . ?
N1 C8 C16 C12 177.27(15) . . . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
N1 H1 N5 0.88 1.93 2.632(2) 135.8 .
N4 H4A O2 0.88 2.21 2.739(2) 117.9 .

_diffrn_measured_fraction_theta_max 0.998
_diffrn_reflns_theta_full        25.34
_diffrn_measured_fraction_theta_full 0.998
_refine_diff_density_max         0.558
_refine_diff_density_min         -0.307
_refine_diff_density_rms         0.047
_contact_Crystallographer_name   'Richard Staples'
_contact_Crystallographer_email  staples@chemistry.msu.com
_database_code_depnum_ccdc_archive 'CCDC 862857'
#######################################################################
#
#                 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_ia5111_0m

_audit_creation_method           SHELXL-97
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_formula_moiety         '(C18 H19 N6 O3 Zn), 0.5(C2 H3 N), (Cl O4)'
_chemical_formula_sum            'C19 H20.50 Cl N6.50 O7 Zn'
_chemical_melting_point          ?

_exptl_crystal_description       needle
_exptl_crystal_colour            yellow

_diffrn_ambient_temperature      173(2)
_chemical_formula_weight         552.74

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'
Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Zn Zn 0.2839 1.4301 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_H-M   'C 2/c'
_symmetry_int_tables_number      15
_chemical_absolute_configuration ?
_symmetry_space_group_name_Hall  '-C 2yc'

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

_cell_length_a                   22.782(2)
_cell_length_b                   7.5608(8)
_cell_length_c                   26.996(3)
_cell_angle_alpha                90.00
_cell_angle_beta                 102.9420(10)
_cell_angle_gamma                90.00
_cell_volume                     4531.9(8)
_cell_formula_units_Z            8
_cell_measurement_temperature    173(2)
_cell_measurement_reflns_used    4025
_cell_measurement_theta_min      2.65
_cell_measurement_theta_max      24.43
_exptl_crystal_size_max          0.46
_exptl_crystal_size_mid          0.07
_exptl_crystal_size_min          0.05
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.620
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             2264
_exptl_absorpt_coefficient_mu    1.258
_exptl_absorpt_correction_type   Multi-scan
_exptl_absorpt_correction_T_min  0.5930
_exptl_absorpt_correction_T_max  0.9386
_exptl_absorpt_process_details   SADABS
_exptl_special_details           
;
Data was collected using a BRUKER CCD (charge coupled device) based
diffractometer equipped with an Oxford low-temperature apparatus operating at
173 K.  A suitable crystal was chosen and mounted on a glass fiber or nylon loop
using Paratone oil for Mo radiation and Mineral oil for Copper radiation.  Data 
were measured using omega and phi scans of 0.5° per frame 
for 30 s. The total number of images were based on 
results from the program COSMO where redundancy was expected to be 4 and 
completeness to 0.83Å to 100%. Cell parameters were
retrieved using APEX II software and refined using SAINT on all observed
reflections.Data reduction was performed using the SAINT software which 
corrects for Lp. Scaling and absorption corrections were applied using SADABS6 
multi-scan technique, supplied by George Sheldrick.  The structures are solved 
by the direct method using the SHELXS-97 program and refined by least squares 
method on F2, SHELXL-97, incorporated in SHELXTL-PC V 6.14. 
 
All H atoms were placed in calculated positions and refined using a riding
model.
C-H(aromatic) = 0.94  Å and Uiso(H) = 1.2Ueq(C)
C-H (alaphatic) = 0.99 Å and Uiso(H) = 1.2Ueq(C)
CH2 = 0.98 Å and Uiso(H) = 1.2Ueq(C)
CH3 = 0.97Å and Uiso(H) = 1.5Ueq(C)
N-H = 0.86 (0.92)Å and Uiso(H) = 1.2 Ueq(N)
O-H(alcohol) = 0.85Åand Uiso(H) = 1.2Ueq(O)
O-H(acid) = 0.82Å and Uiso(H) = 1.5Ueq(O)
;
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'ω,and/f 0.5 deg'
_diffrn_detector_area_resol_mean 836.6
_diffrn_reflns_number            18054
_diffrn_reflns_av_R_equivalents  0.0710
_diffrn_reflns_av_sigmaI/netI    0.0647
_diffrn_reflns_limit_h_min       -27
_diffrn_reflns_limit_h_max       27
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_l_min       -32
_diffrn_reflns_limit_l_max       32
_diffrn_reflns_theta_min         1.83
_diffrn_reflns_theta_max         25.59
_reflns_number_total             4252
_reflns_number_gt                2524
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'COSMO (BRUKER, V1.61, 2009)'
_computing_cell_refinement       'APEX2 (BRUKER, V2010.11-3, 2010)'
_computing_data_reduction        'SAINT (BRUKER, V7.68A, 2010)'
_computing_structure_solution    
'SHELXS (Sheldrick, Acta Cryst. A64 2008, 112-122)'
_computing_structure_refinement  
'SHELXL (Sheldrick, Acta Cryst. A64 2008, 112-122)'
_computing_molecular_graphics    
'SHELXTL (Sheldrick, Acta Cryst. A64 2008, 112-122)'
_computing_publication_material  
'SHELXTL (Sheldrick, Acta Cryst. A64 2008, 112-122)'

_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)+(0.0841P)²+16.4842P] 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         4252
_refine_ls_number_parameters     352
_refine_ls_number_restraints     54
_refine_ls_R_factor_all          0.1222
_refine_ls_R_factor_gt           0.0678
_refine_ls_wR_factor_ref         0.1888
_refine_ls_wR_factor_gt          0.1595
_refine_ls_goodness_of_fit_ref   1.023
_refine_ls_restrained_S_all      1.118
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
Zn1 Zn 0.02965(3) 0.67855(11) 0.44701(3) 0.0512(3) Uani 1 1 d . . .
O1W O 0.0550(3) 0.8625(7) 0.40132(19) 0.0745(16) Uani 1 1 d D . .
H1W H 0.080(3) 0.837(10) 0.383(2) 0.089 Uiso 1 1 d D . .
H2W H 0.028(3) 0.939(9) 0.385(2) 0.089 Uiso 1 1 d D . .
O1 O 0.1243(3) 0.8306(9) 0.65238(19) 0.105(2) Uani 1 1 d . . .
O2 O 0.0300(3) 0.9164(8) 0.64398(16) 0.0735(15) Uani 1 1 d . . .
N1 N -0.0155(2) 0.7642(7) 0.50024(18) 0.0459(13) Uani 1 1 d . . .
N2 N 0.0037(2) 0.8141(7) 0.54751(18) 0.0476(13) Uani 1 1 d . . .
N3 N -0.0599(3) 0.6653(8) 0.4048(2) 0.0618(16) Uani 1 1 d . . .
N4 N 0.1035(2) 0.6675(8) 0.5027(2) 0.0528(14) Uani 1 1 d . . .
N5 N 0.1668(3) 0.7074(10) 0.5760(3) 0.075(2) Uani 1 1 d . . .
H5A H 0.180(3) 0.750(10) 0.607(3) 0.07(2) Uiso 1 1 d . . .
N6 N 0.0577(3) 0.4751(9) 0.4026(2) 0.0623(16) Uani 1 1 d . . .
C1 C 0.0602(3) 0.7962(9) 0.5716(2) 0.0500(17) Uani 1 1 d . . .
C2 C 0.0688(4) 0.8539(10) 0.6251(2) 0.064(2) Uani 1 1 d . . .
C3 C 0.1332(7) 0.8838(19) 0.7059(3) 0.187(8) Uani 1 1 d . . .
H3A H 0.1368 1.0143 0.7079 0.224 Uiso 1 1 calc R . .
H3B H 0.0970 0.8502 0.7182 0.224 Uiso 1 1 calc R . .
C4 C 0.1781(7) 0.8184(17) 0.7348(3) 0.160(6) Uani 1 1 d . . .
H4A H 0.1807 0.8615 0.7695 0.240 Uiso 1 1 calc R . .
H4B H 0.2145 0.8528 0.7236 0.240 Uiso 1 1 calc R . .
H4C H 0.1745 0.6892 0.7343 0.240 Uiso 1 1 calc R . .
C5 C -0.0780(3) 0.7907(9) 0.4810(3) 0.0535(18) Uani 1 1 d . . .
C6 C -0.1177(3) 0.8630(11) 0.5071(3) 0.072(2) Uani 1 1 d . . .
H6A H -0.1037 0.8998 0.5413 0.086 Uiso 1 1 calc R . .
C7 C -0.1785(4) 0.8825(13) 0.4834(5) 0.101(3) Uani 1 1 d . . .
H7A H -0.2054 0.9312 0.5021 0.122 Uiso 1 1 calc R . .
C8 C -0.2000(4) 0.8333(14) 0.4343(6) 0.123(5) Uani 1 1 d . . .
H8A H -0.2414 0.8495 0.4189 0.148 Uiso 1 1 calc R . .
C9 C -0.1614(4) 0.7586(13) 0.4064(4) 0.098(3) Uani 1 1 d . . .
C10 C -0.0996(3) 0.7366(11) 0.4295(3) 0.067(2) Uani 1 1 d . . .
C11 C -0.0796(4) 0.6153(12) 0.3567(3) 0.085(3) Uani 1 1 d . . .
H11A H -0.0518 0.5657 0.3391 0.101 Uiso 1 1 calc R . .
C12 C -0.1392(6) 0.6331(17) 0.3314(4) 0.128(5) Uani 1 1 d . . .
H12A H -0.1519 0.5940 0.2972 0.153 Uiso 1 1 calc R . .
C13 C -0.1788(6) 0.7046(16) 0.3549(5) 0.128(5) Uani 1 1 d . . .
H13A H -0.2193 0.7199 0.3369 0.154 Uiso 1 1 calc R . .
C14 C 0.1085(3) 0.7241(9) 0.5508(2) 0.0489(16) Uani 1 1 d . . .
C15 C 0.1605(3) 0.6177(11) 0.4989(3) 0.069(2) Uani 1 1 d . . .
H15A H 0.1706 0.5723 0.4691 0.083 Uiso 1 1 calc R . .
C16 C 0.1996(4) 0.6427(12) 0.5435(4) 0.086(3) Uani 1 1 d . . .
H16A H 0.2416 0.6199 0.5510 0.104 Uiso 1 1 calc R . .
C17 C 0.0767(3) 0.3869(11) 0.3764(3) 0.061(2) Uani 1 1 d . . .
C18 C 0.0999(4) 0.2751(12) 0.3420(3) 0.088(3) Uani 1 1 d . . .
H18A H 0.1286 0.1904 0.3615 0.132 Uiso 1 1 calc R . .
H18B H 0.1203 0.3481 0.3210 0.132 Uiso 1 1 calc R . .
H18C H 0.0666 0.2110 0.3201 0.132 Uiso 1 1 calc R . .
N1S N 0.0000 0.493(2) 0.2500 0.108(4) Uani 1 2 d S . .
C1S C 0.0000 0.641(3) 0.2500 0.084(5) Uani 1 2 d S . .
C2S C 0.0000 0.827(2) 0.2500 0.104(5) Uani 1 2 d S . .
H2S1 H -0.0231 0.8699 0.2741 0.155 Uiso 0.50 1 calc PR . .
H2S2 H -0.0184 0.8699 0.2158 0.155 Uiso 0.50 1 calc PR . .
H2S3 H 0.0415 0.8699 0.2601 0.155 Uiso 0.50 1 calc PR . .
Cl1 Cl 0.17969(8) 0.7540(3) 0.33506(7) 0.0696(6) Uani 1 1 d D . .
O3A O 0.1569(6) 0.8698(17) 0.3714(6) 0.125(5) Uani 0.50 1 d PD A 1
O4A O 0.1353(6) 0.749(3) 0.2952(5) 0.204(14) Uani 0.50 1 d PD A 1
O5A O 0.1959(9) 0.6049(18) 0.3608(8) 0.150(12) Uani 0.50 1 d PD A 1
O3B O 0.1258(5) 0.825(2) 0.3263(7) 0.126(6) Uani 0.50 1 d PD A 2
O4B O 0.1775(9) 0.620(2) 0.2964(7) 0.197(12) Uani 0.50 1 d PD A 2
O5B O 0.1910(8) 0.655(2) 0.3793(6) 0.137(11) Uani 0.50 1 d PD A 2
O6 O 0.2290(3) 0.8560(9) 0.3325(3) 0.118(3) Uani 1 1 d D A .


_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 N4 1.991(5) . ?
Zn1 O1W 2.027(5) . ?
Zn1 N1 2.050(5) . ?
Zn1 N3 2.105(6) . ?
Zn1 N6 2.133(6) . ?
O1W H1W 0.87(2) . ?
O1W H2W 0.88(2) . ?
O1 C2 1.325(9) . ?
O1 C3 1.470(10) . ?
O2 C2 1.211(8) . ?
N1 N2 1.308(7) . ?
N1 C5 1.417(8) . ?
N2 C1 1.314(8) . ?
N3 C11 1.331(9) . ?
N3 C10 1.350(10) . ?
N4 C14 1.347(8) . ?
N4 C15 1.376(8) . ?
N5 C14 1.355(8) . ?
N5 C16 1.363(11) . ?
N5 H5A 0.89(7) . ?
N6 C17 1.128(8) . ?
C1 C14 1.450(9) . ?
C1 C2 1.479(9) . ?
C3 C4 1.241(13) . ?
C3 H3A 0.9900 . ?
C3 H3B 0.9900 . ?
C4 H4A 0.9800 . ?
C4 H4B 0.9800 . ?
C4 H4C 0.9800 . ?
C5 C6 1.380(10) . ?
C5 C10 1.425(10) . ?
C6 C7 1.397(11) . ?
C6 H6A 0.9500 . ?
C7 C8 1.359(15) . ?
C7 H7A 0.9500 . ?
C8 C9 1.400(15) . ?
C8 H8A 0.9500 . ?
C9 C10 1.416(11) . ?
C9 C13 1.418(15) . ?
C11 C12 1.383(14) . ?
C11 H11A 0.9500 . ?
C12 C13 1.327(17) . ?
C12 H12A 0.9500 . ?
C13 H13A 0.9500 . ?
C15 C16 1.340(11) . ?
C15 H15A 0.9500 . ?
C16 H16A 0.9500 . ?
C17 C18 1.441(10) . ?
C18 H18A 0.9800 . ?
C18 H18B 0.9800 . ?
C18 H18C 0.9800 . ?
N1S C1S 1.118(18) . ?
C1S C2S 1.41(2) . ?
C2S H2S1 0.9800 . ?
C2S H2S2 0.9800 . ?
C2S H2S3 0.9800 . ?
Cl1 O4A 1.301(9) . ?
Cl1 O3B 1.312(9) . ?
Cl1 O5A 1.332(11) . ?
Cl1 O6 1.376(6) . ?
Cl1 O5B 1.383(11) . ?
Cl1 O4B 1.448(9) . ?
Cl1 O3A 1.492(11) . ?

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
N4 Zn1 O1W 100.4(2) . . ?
N4 Zn1 N1 87.5(2) . . ?
O1W Zn1 N1 117.7(2) . . ?
N4 Zn1 N3 163.7(2) . . ?
O1W Zn1 N3 94.4(2) . . ?
N1 Zn1 N3 79.5(2) . . ?
N4 Zn1 N6 94.9(2) . . ?
O1W Zn1 N6 89.5(2) . . ?
N1 Zn1 N6 151.8(2) . . ?
N3 Zn1 N6 92.2(2) . . ?
Zn1 O1W H1W 121(5) . . ?
Zn1 O1W H2W 119(5) . . ?
H1W O1W H2W 110(5) . . ?
C2 O1 C3 114.5(8) . . ?
N2 N1 C5 113.9(5) . . ?
N2 N1 Zn1 131.7(4) . . ?
C5 N1 Zn1 114.1(4) . . ?
N1 N2 C1 122.0(5) . . ?
C11 N3 C10 118.6(7) . . ?
C11 N3 Zn1 128.0(6) . . ?
C10 N3 Zn1 112.9(5) . . ?
C14 N4 C15 106.3(6) . . ?
C14 N4 Zn1 126.0(4) . . ?
C15 N4 Zn1 127.4(5) . . ?
C14 N5 C16 109.1(7) . . ?
C14 N5 H5A 121(5) . . ?
C16 N5 H5A 129(5) . . ?
C17 N6 Zn1 169.9(6) . . ?
N2 C1 C14 126.2(6) . . ?
N2 C1 C2 110.8(6) . . ?
C14 C1 C2 123.0(6) . . ?
O2 C2 O1 121.0(6) . . ?
O2 C2 C1 125.2(7) . . ?
O1 C2 C1 113.9(7) . . ?
C4 C3 O1 115.0(9) . . ?
C4 C3 H3A 108.5 . . ?
O1 C3 H3A 108.5 . . ?
C4 C3 H3B 108.5 . . ?
O1 C3 H3B 108.5 . . ?
H3A C3 H3B 107.5 . . ?
C3 C4 H4A 109.5 . . ?
C3 C4 H4B 109.5 . . ?
H4A C4 H4B 109.5 . . ?
C3 C4 H4C 109.5 . . ?
H4A C4 H4C 109.5 . . ?
H4B C4 H4C 109.5 . . ?
C6 C5 N1 126.1(7) . . ?
C6 C5 C10 119.2(7) . . ?
N1 C5 C10 114.7(6) . . ?
C5 C6 C7 120.3(8) . . ?
C5 C6 H6A 119.8 . . ?
C7 C6 H6A 119.8 . . ?
C8 C7 C6 121.4(9) . . ?
C8 C7 H7A 119.3 . . ?
C6 C7 H7A 119.3 . . ?
C7 C8 C9 120.2(9) . . ?
C7 C8 H8A 119.9 . . ?
C9 C8 H8A 119.9 . . ?
C8 C9 C10 119.6(10) . . ?
C8 C9 C13 124.9(10) . . ?
C10 C9 C13 115.5(11) . . ?
N3 C10 C9 122.6(8) . . ?
N3 C10 C5 118.2(6) . . ?
C9 C10 C5 119.2(8) . . ?
N3 C11 C12 122.3(10) . . ?
N3 C11 H11A 118.9 . . ?
C12 C11 H11A 118.9 . . ?
C13 C12 C11 120.0(10) . . ?
C13 C12 H12A 120.0 . . ?
C11 C12 H12A 120.0 . . ?
C12 C13 C9 121.0(10) . . ?
C12 C13 H13A 119.5 . . ?
C9 C13 H13A 119.5 . . ?
N4 C14 N5 108.4(6) . . ?
N4 C14 C1 125.9(6) . . ?
N5 C14 C1 125.6(6) . . ?
C16 C15 N4 110.1(7) . . ?
C16 C15 H15A 125.0 . . ?
N4 C15 H15A 125.0 . . ?
C15 C16 N5 106.2(7) . . ?
C15 C16 H16A 126.9 . . ?
N5 C16 H16A 126.9 . . ?
N6 C17 C18 178.7(9) . . ?
C17 C18 H18A 109.5 . . ?
C17 C18 H18B 109.5 . . ?
H18A C18 H18B 109.5 . . ?
C17 C18 H18C 109.5 . . ?
H18A C18 H18C 109.5 . . ?
H18B C18 H18C 109.5 . . ?
N1S C1S C2S 180.000(10) . . ?
C1S C2S H2S1 109.5 . . ?
C1S C2S H2S2 109.5 . . ?
H2S1 C2S H2S2 109.5 . . ?
C1S C2S H2S3 109.5 . . ?
H2S1 C2S H2S3 109.5 . . ?
H2S2 C2S H2S3 109.5 . . ?
O4A Cl1 O3B 48.6(9) . . ?
O4A Cl1 O5A 118.8(10) . . ?
O3B Cl1 O5A 125.5(13) . . ?
O4A Cl1 O6 117.7(8) . . ?
O3B Cl1 O6 120.1(8) . . ?
O5A Cl1 O6 111.4(9) . . ?
O4A Cl1 O5B 131.3(12) . . ?
O3B Cl1 O5B 111.4(9) . . ?
O5A Cl1 O5B 27.9(14) . . ?
O6 Cl1 O5B 110.4(8) . . ?
O4A Cl1 O4B 59.4(12) . . ?
O3B Cl1 O4B 106.1(9) . . ?
O5A Cl1 O4B 75.2(13) . . ?
O6 Cl1 O4B 104.6(7) . . ?
O5B Cl1 O4B 102.4(9) . . ?
O4A Cl1 O3A 103.8(9) . . ?
O3B Cl1 O3A 55.2(8) . . ?
O5A Cl1 O3A 104.5(9) . . ?
O6 Cl1 O3A 96.4(6) . . ?
O5B Cl1 O3A 77.0(11) . . ?
O4B Cl1 O3A 157.5(8) . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
N4 Zn1 N1 N2 9.7(6) . . . . ?
O1W Zn1 N1 N2 -90.7(6) . . . . ?
N3 Zn1 N1 N2 179.8(6) . . . . ?
N6 Zn1 N1 N2 105.3(6) . . . . ?
N4 Zn1 N1 C5 -177.4(5) . . . . ?
O1W Zn1 N1 C5 82.2(5) . . . . ?
N3 Zn1 N1 C5 -7.3(5) . . . . ?
N6 Zn1 N1 C5 -81.8(6) . . . . ?
C5 N1 N2 C1 178.8(6) . . . . ?
Zn1 N1 N2 C1 -8.4(9) . . . . ?
N4 Zn1 N3 C11 -143.0(8) . . . . ?
O1W Zn1 N3 C11 62.2(7) . . . . ?
N1 Zn1 N3 C11 179.6(7) . . . . ?
N6 Zn1 N3 C11 -27.5(7) . . . . ?
N4 Zn1 N3 C10 45.1(12) . . . . ?
O1W Zn1 N3 C10 -109.8(5) . . . . ?
N1 Zn1 N3 C10 7.7(5) . . . . ?
N6 Zn1 N3 C10 160.6(5) . . . . ?
O1W Zn1 N4 C14 111.3(6) . . . . ?
N1 Zn1 N4 C14 -6.5(6) . . . . ?
N3 Zn1 N4 C14 -43.2(12) . . . . ?
N6 Zn1 N4 C14 -158.3(6) . . . . ?
O1W Zn1 N4 C15 -61.9(7) . . . . ?
N1 Zn1 N4 C15 -179.7(6) . . . . ?
N3 Zn1 N4 C15 143.6(8) . . . . ?
N6 Zn1 N4 C15 28.5(7) . . . . ?
N4 Zn1 N6 C17 -86(4) . . . . ?
O1W Zn1 N6 C17 15(4) . . . . ?
N1 Zn1 N6 C17 -179(100) . . . . ?
N3 Zn1 N6 C17 109(4) . . . . ?
N1 N2 C1 C14 0.9(10) . . . . ?
N1 N2 C1 C2 -176.9(6) . . . . ?
C3 O1 C2 O2 0.9(13) . . . . ?
C3 O1 C2 C1 -178.7(9) . . . . ?
N2 C1 C2 O2 -3.0(11) . . . . ?
C14 C1 C2 O2 179.2(7) . . . . ?
N2 C1 C2 O1 176.7(6) . . . . ?
C14 C1 C2 O1 -1.2(11) . . . . ?
C2 O1 C3 C4 160.2(14) . . . . ?
N2 N1 C5 C6 0.6(10) . . . . ?
Zn1 N1 C5 C6 -173.5(6) . . . . ?
N2 N1 C5 C10 -179.8(6) . . . . ?
Zn1 N1 C5 C10 6.0(8) . . . . ?
N1 C5 C6 C7 179.7(8) . . . . ?
C10 C5 C6 C7 0.2(12) . . . . ?
C5 C6 C7 C8 -0.8(15) . . . . ?
C6 C7 C8 C9 1.0(18) . . . . ?
C7 C8 C9 C10 -0.7(17) . . . . ?
C7 C8 C9 C13 -179.2(11) . . . . ?
C11 N3 C10 C9 0.6(12) . . . . ?
Zn1 N3 C10 C9 173.3(7) . . . . ?
C11 N3 C10 C5 -179.6(7) . . . . ?
Zn1 N3 C10 C5 -6.9(9) . . . . ?
C8 C9 C10 N3 179.9(9) . . . . ?
C13 C9 C10 N3 -1.4(14) . . . . ?
C8 C9 C10 C5 0.1(14) . . . . ?
C13 C9 C10 C5 178.8(9) . . . . ?
C6 C5 C10 N3 -179.7(7) . . . . ?
N1 C5 C10 N3 0.8(10) . . . . ?
C6 C5 C10 C9 0.1(12) . . . . ?
N1 C5 C10 C9 -179.4(7) . . . . ?
C10 N3 C11 C12 -0.3(13) . . . . ?
Zn1 N3 C11 C12 -171.9(8) . . . . ?
N3 C11 C12 C13 1.1(18) . . . . ?
C11 C12 C13 C9 -2(2) . . . . ?
C8 C9 C13 C12 -179.2(13) . . . . ?
C10 C9 C13 C12 2.2(18) . . . . ?
C15 N4 C14 N5 -0.7(8) . . . . ?
Zn1 N4 C14 N5 -175.1(5) . . . . ?
C15 N4 C14 C1 177.4(7) . . . . ?
Zn1 N4 C14 C1 3.0(10) . . . . ?
C16 N5 C14 N4 1.1(9) . . . . ?
C16 N5 C14 C1 -177.0(7) . . . . ?
N2 C1 C14 N4 1.7(12) . . . . ?
C2 C1 C14 N4 179.3(7) . . . . ?
N2 C1 C14 N5 179.5(7) . . . . ?
C2 C1 C14 N5 -3.0(12) . . . . ?
C14 N4 C15 C16 0.0(9) . . . . ?
Zn1 N4 C15 C16 174.3(6) . . . . ?
N4 C15 C16 N5 0.6(11) . . . . ?
C14 N5 C16 C15 -1.0(11) . . . . ?
Zn1 N6 C17 C18 -83(40) . . . . ?

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
O1W H1W O3A 0.87(2) 1.85(5) 2.624(12) 147(8) .
O1W H1W O3B 0.87(2) 2.02(3) 2.872(16) 165(6) .
O1W H2W O2 0.88(2) 1.36(6) 2.074(7) 135(7) ?
N5 H5A O1 0.89(7) 2.03(7) 2.636(9) 124(6) .

_diffrn_measured_fraction_theta_max 0.998
_diffrn_reflns_theta_full        25.59
_diffrn_measured_fraction_theta_full 0.998
_refine_diff_density_max         0.552
_refine_diff_density_min         -0.431
_refine_diff_density_rms         0.086
_contact_Crystallographer_name   'Richard Staples'
_contact_Crystallographer_email  staples@chemistry.msu.com
_database_code_depnum_ccdc_archive 'CCDC 990962'
