# Electronic Supplementary Material (ESI) for RSC Advances.
# 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_shelxl
#TrackingRef 'akr AH 2.cif'


_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C13 H14 N6 O2'
_chemical_formula_weight         286.30

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           Triclinic
_symmetry_space_group_name_H-M   P-1

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

_cell_length_a                   8.282(5)
_cell_length_b                   9.501(5)
_cell_length_c                   9.604(5)
_cell_angle_alpha                106.753(5)
_cell_angle_beta                 100.835(5)
_cell_angle_gamma                100.556(5)
_cell_volume                     687.7(7)
_cell_formula_units_Z            2
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    5255
_cell_measurement_theta_min      2.588
_cell_measurement_theta_max      32.237

_exptl_crystal_description       block
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.30
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.20
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.383
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             300
_exptl_absorpt_coefficient_mu    0.099
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.9534
_exptl_absorpt_correction_T_max  0.9943
_exptl_absorpt_process_details   'SADABS (Bruker, 1999)'

_exptl_special_details           
;
?
;

_diffrn_ambient_temperature      293(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 axs kappa apex2 CCD Diffractometer'
_diffrn_measurement_method       'ω and φ scan'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            8477
_diffrn_reflns_av_R_equivalents  0.0217
_diffrn_reflns_av_sigmaI/netI    0.0185
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_theta_min         2.29
_diffrn_reflns_theta_max         25.00
_reflns_number_total             2420
_reflns_number_gt                2160
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'APEX2 (Bruker, 2004)'
_computing_cell_refinement       'APEX2/SAINT (Bruker, 2004)'
_computing_data_reduction        'SAINT/XPREP (Bruker, 2004)'
_computing_structure_solution    'SIR92 (Altornare et al., 1993)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_molecular_graphics    
'ORTEP3 (Farrugia, 1997) and Mercury (Bruno et al., 2002)'
_computing_publication_material  'SHELXL-97 (Sheldrick, 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 > 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)+(0.0586P)²+0.2008P] 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     SHELXL
_refine_ls_extinction_coef       0.041(6)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_number_reflns         2420
_refine_ls_number_parameters     199
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0444
_refine_ls_R_factor_gt           0.0399
_refine_ls_wR_factor_ref         0.1141
_refine_ls_wR_factor_gt          0.1091
_refine_ls_goodness_of_fit_ref   1.066
_refine_ls_restrained_S_all      1.066
_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
C1 C 0.13608(19) 0.17420(17) 0.45656(16) 0.0353(3) Uani 1 1 d . . .
C2 C 0.21012(19) 0.37537(17) 0.34582(16) 0.0338(3) Uani 1 1 d . . .
C3 C 0.02200(19) 0.37035(16) 0.32526(16) 0.0360(4) Uani 1 1 d . . .
C4 C -0.08927(19) 0.26037(17) 0.34727(16) 0.0366(4) Uani 1 1 d . . .
C5 C -0.2775(2) 0.2371(2) 0.3187(2) 0.0508(4) Uani 1 1 d . . .
H5A H -0.3248 0.1507 0.3442 0.076 Uiso 1 1 calc R . .
H5B H -0.3256 0.2198 0.2144 0.076 Uiso 1 1 calc R . .
H5C H -0.3029 0.3258 0.3793 0.076 Uiso 1 1 calc R . .
C6 C 0.25713(18) 0.31048(15) 0.19882(15) 0.0320(3) Uani 1 1 d . . .
C7 C 0.2085(2) 0.1057(2) -0.01124(19) 0.0537(5) Uani 1 1 d . . .
H7 H 0.1472 0.0075 -0.0706 0.064 Uiso 1 1 calc R . .
C8 C 0.3347(2) 0.1774(2) -0.06007(19) 0.0495(4) Uani 1 1 d . . .
H8 H 0.3587 0.1286 -0.1498 0.059 Uiso 1 1 calc R . .
C9 C 0.4243(2) 0.3222(2) 0.0265(2) 0.0516(5) Uani 1 1 d . . .
H9 H 0.5109 0.3737 -0.0034 0.062 Uiso 1 1 calc R . .
C10 C 0.3846(2) 0.39099(18) 0.15839(19) 0.0430(4) Uani 1 1 d . . .
H10 H 0.4429 0.4898 0.2186 0.052 Uiso 1 1 calc R . .
C11 C -0.0357(2) 0.48794(18) 0.27282(19) 0.0430(4) Uani 1 1 d . . .
C12 C 0.0519(3) 0.6969(2) 0.1926(3) 0.0620(5) Uani 1 1 d . . .
H12A H 0.0112 0.7667 0.2649 0.074 Uiso 1 1 calc R . .
H12B H -0.0367 0.6526 0.0992 0.074 Uiso 1 1 calc R . .
C13 C 0.2054(3) 0.7776(3) 0.1671(4) 0.0958(9) Uani 1 1 d . . .
H13A H 0.1806 0.8564 0.1291 0.144 Uiso 1 1 calc R . .
H13B H 0.2447 0.7077 0.0953 0.144 Uiso 1 1 calc R . .
H13C H 0.2920 0.8217 0.2602 0.144 Uiso 1 1 calc R . .
N1 N 0.24807(15) 0.28336(14) 0.44046(13) 0.0347(3) Uani 1 1 d . . .
N2 N 0.40580(17) 0.28015(16) 0.50850(15) 0.0453(4) Uani 1 1 d . . .
N3 N 0.38407(18) 0.17207(18) 0.56429(17) 0.0522(4) Uani 1 1 d . . .
N4 N 0.21567(17) 0.10171(16) 0.53362(16) 0.0461(4) Uani 1 1 d . . .
N5 N -0.03250(17) 0.15455(16) 0.40300(15) 0.0410(3) Uani 1 1 d . . .
N6 N 0.16908(18) 0.16952(15) 0.11676(15) 0.0473(4) Uani 1 1 d . . .
O1 O 0.09311(15) 0.57825(14) 0.24943(15) 0.0539(4) Uani 1 1 d . . .
O2 O -0.17637(17) 0.50706(17) 0.25343(19) 0.0708(4) Uani 1 1 d . . .
H2 H 0.279(2) 0.4762(19) 0.3971(18) 0.035(4) Uiso 1 1 d . . .
H5D H -0.103(2) 0.085(2) 0.420(2) 0.050(5) 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
C1 N4 1.317(2) . ?
C1 N1 1.324(2) . ?
C1 N5 1.352(2) . ?
C2 N1 1.4630(19) . ?
C2 C6 1.522(2) . ?
C2 C3 1.523(2) . ?
C2 H2 0.953(17) . ?
C3 C4 1.354(2) . ?
C3 C11 1.470(2) . ?
C4 N5 1.381(2) . ?
C4 C5 1.494(2) . ?
C5 H5A 0.9600 . ?
C5 H5B 0.9600 . ?
C5 H5C 0.9600 . ?
C6 N6 1.328(2) . ?
C6 C10 1.371(2) . ?
C7 N6 1.334(2) . ?
C7 C8 1.372(2) . ?
C7 H7 0.9300 . ?
C8 C9 1.367(3) . ?
C8 H8 0.9300 . ?
C9 C10 1.378(2) . ?
C9 H9 0.9300 . ?
C10 H10 0.9300 . ?
C11 O2 1.200(2) . ?
C11 O1 1.338(2) . ?
C12 O1 1.453(2) . ?
C12 C13 1.461(3) . ?
C12 H12A 0.9700 . ?
C12 H12B 0.9700 . ?
C13 H13A 0.9600 . ?
C13 H13B 0.9600 . ?
C13 H13C 0.9600 . ?
N1 N2 1.3562(19) . ?
N2 N3 1.288(2) . ?
N3 N4 1.367(2) . ?
N5 H5D 0.87(2) . ?

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 C1 N1 109.69(14) . . ?
N4 C1 N5 129.42(14) . . ?
N1 C1 N5 120.83(13) . . ?
N1 C2 C6 108.36(12) . . ?
N1 C2 C3 106.52(11) . . ?
C6 C2 C3 113.49(12) . . ?
N1 C2 H2 107.9(9) . . ?
C6 C2 H2 109.1(9) . . ?
C3 C2 H2 111.2(9) . . ?
C4 C3 C11 120.99(14) . . ?
C4 C3 C2 122.52(14) . . ?
C11 C3 C2 116.44(13) . . ?
C3 C4 N5 120.43(14) . . ?
C3 C4 C5 127.06(15) . . ?
N5 C4 C5 112.50(14) . . ?
C4 C5 H5A 109.5 . . ?
C4 C5 H5B 109.5 . . ?
H5A C5 H5B 109.5 . . ?
C4 C5 H5C 109.5 . . ?
H5A C5 H5C 109.5 . . ?
H5B C5 H5C 109.5 . . ?
N6 C6 C10 123.31(14) . . ?
N6 C6 C2 114.75(13) . . ?
C10 C6 C2 121.90(13) . . ?
N6 C7 C8 123.50(16) . . ?
N6 C7 H7 118.3 . . ?
C8 C7 H7 118.3 . . ?
C9 C8 C7 118.37(15) . . ?
C9 C8 H8 120.8 . . ?
C7 C8 H8 120.8 . . ?
C8 C9 C10 119.15(15) . . ?
C8 C9 H9 120.4 . . ?
C10 C9 H9 120.4 . . ?
C6 C10 C9 118.50(15) . . ?
C6 C10 H10 120.8 . . ?
C9 C10 H10 120.8 . . ?
O2 C11 O1 122.02(16) . . ?
O2 C11 C3 127.22(16) . . ?
O1 C11 C3 110.75(14) . . ?
O1 C12 C13 108.21(17) . . ?
O1 C12 H12A 110.1 . . ?
C13 C12 H12A 110.1 . . ?
O1 C12 H12B 110.1 . . ?
C13 C12 H12B 110.1 . . ?
H12A C12 H12B 108.4 . . ?
C12 C13 H13A 109.5 . . ?
C12 C13 H13B 109.5 . . ?
H13A C13 H13B 109.5 . . ?
C12 C13 H13C 109.5 . . ?
H13A C13 H13C 109.5 . . ?
H13B C13 H13C 109.5 . . ?
C1 N1 N2 108.28(12) . . ?
C1 N1 C2 125.56(13) . . ?
N2 N1 C2 125.52(12) . . ?
N3 N2 N1 105.94(13) . . ?
N2 N3 N4 111.37(13) . . ?
C1 N4 N3 104.72(13) . . ?
C1 N5 C4 119.50(13) . . ?
C1 N5 H5D 118.5(13) . . ?
C4 N5 H5D 121.0(13) . . ?
C6 N6 C7 117.17(14) . . ?
C11 O1 C12 116.32(14) . . ?

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
N1 C2 C3 C4 -20.18(18) . . . . ?
C6 C2 C3 C4 98.97(16) . . . . ?
N1 C2 C3 C11 162.63(12) . . . . ?
C6 C2 C3 C11 -78.22(16) . . . . ?
C11 C3 C4 N5 -177.08(13) . . . . ?
C2 C3 C4 N5 5.8(2) . . . . ?
C11 C3 C4 C5 2.3(2) . . . . ?
C2 C3 C4 C5 -174.72(15) . . . . ?
N1 C2 C6 N6 62.81(17) . . . . ?
C3 C2 C6 N6 -55.28(17) . . . . ?
N1 C2 C6 C10 -115.15(15) . . . . ?
C3 C2 C6 C10 126.76(15) . . . . ?
N6 C7 C8 C9 -0.4(3) . . . . ?
C7 C8 C9 C10 -0.3(3) . . . . ?
N6 C6 C10 C9 -0.4(2) . . . . ?
C2 C6 C10 C9 177.40(15) . . . . ?
C8 C9 C10 C6 0.6(3) . . . . ?
C4 C3 C11 O2 5.0(3) . . . . ?
C2 C3 C11 O2 -177.76(17) . . . . ?
C4 C3 C11 O1 -175.89(13) . . . . ?
C2 C3 C11 O1 1.34(19) . . . . ?
N4 C1 N1 N2 0.58(17) . . . . ?
N5 C1 N1 N2 177.97(13) . . . . ?
N4 C1 N1 C2 171.83(13) . . . . ?
N5 C1 N1 C2 -10.8(2) . . . . ?
C6 C2 N1 C1 -99.37(16) . . . . ?
C3 C2 N1 C1 23.07(18) . . . . ?
C6 C2 N1 N2 70.40(17) . . . . ?
C3 C2 N1 N2 -167.15(13) . . . . ?
C1 N1 N2 N3 -0.80(17) . . . . ?
C2 N1 N2 N3 -172.06(13) . . . . ?
N1 N2 N3 N4 0.74(18) . . . . ?
N1 C1 N4 N3 -0.13(17) . . . . ?
N5 C1 N4 N3 -177.22(15) . . . . ?
N2 N3 N4 C1 -0.40(19) . . . . ?
N4 C1 N5 C4 168.92(15) . . . . ?
N1 C1 N5 C4 -7.9(2) . . . . ?
C3 C4 N5 C1 9.8(2) . . . . ?
C5 C4 N5 C1 -169.68(14) . . . . ?
C10 C6 N6 C7 -0.3(2) . . . . ?
C2 C6 N6 C7 -178.20(15) . . . . ?
C8 C7 N6 C6 0.7(3) . . . . ?
O2 C11 O1 C12 -2.7(3) . . . . ?
C3 C11 O1 C12 178.12(14) . . . . ?
C13 C12 O1 C11 -177.10(19) . . . . ?

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
N5 H5D N4 0.87(2) 2.05(2) 2.906(2) 165.3(18) 2_556

_diffrn_measured_fraction_theta_max 0.997
_diffrn_reflns_theta_full        25.00
_diffrn_measured_fraction_theta_full 0.997
_refine_diff_density_max         0.260
_refine_diff_density_min         -0.222
_refine_diff_density_rms         0.039


_database_code_depnum_ccdc_archive 'CCDC 881456'
#######################################################################
#
#                 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_shelxl

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C13 H16 N6 O3'
_chemical_formula_weight         304.32

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           orthorhombic
_symmetry_space_group_name_H-M   Pbca

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

_cell_length_a                   9.3144(3)
_cell_length_b                   17.8682(5)
_cell_length_c                   18.0638(6)
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_volume                     3006.39(16)
_cell_formula_units_Z            8
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    2640
_cell_measurement_theta_min      2.71
_cell_measurement_theta_max      29.0

_exptl_crystal_description       block
_exptl_crystal_colour            colourles
_exptl_crystal_size_max          0.30
_exptl_crystal_size_mid          0.25
_exptl_crystal_size_min          0.15
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.345
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1280
_exptl_absorpt_coefficient_mu    0.100
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.9707
_exptl_absorpt_correction_T_max  0.9852
_exptl_absorpt_process_details   'CrysAlis RED (Oxford Diffraction, 2007)'

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      293(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  
'Oxford Diffraction Xcalibur CCD diffractometer'
_diffrn_measurement_method       'ω and φ scan'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            16734
_diffrn_reflns_av_R_equivalents  0.0459
_diffrn_reflns_av_sigmaI/netI    0.0338
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_k_min       -21
_diffrn_reflns_limit_k_max       21
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_theta_min         2.71
_diffrn_reflns_theta_max         25.00
_reflns_number_total             2640
_reflns_number_gt                1856
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'CrysAlis Pro (Oxford Diffraction, 2004)'
_computing_cell_refinement       'CrysAlis Pro (Oxford Diffraction, 2007)'
_computing_data_reduction        'CrysAlis RED (Oxford Diffraction, 2007)'
_computing_structure_solution    'SIR92 (Altomare et al., 1993)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    
'ORTEP3 (Farrugia, 1997) and Mercury (Bruno et al., 2002)'
_computing_publication_material  'SHELXL-97 (Sheldrick, 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 > 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)+(0.0586P)²+0.5934P] 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         2640
_refine_ls_number_parameters     232
_refine_ls_number_restraints     19
_refine_ls_R_factor_all          0.0739
_refine_ls_R_factor_gt           0.0468
_refine_ls_wR_factor_ref         0.1298
_refine_ls_wR_factor_gt          0.1142
_refine_ls_goodness_of_fit_ref   1.054
_refine_ls_restrained_S_all      1.053
_refine_ls_shift/su_max          0.002
_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 0.1488(14) 0.2482(9) 0.6885(8) 0.117(5) Uani 0.66(2) 1 d PDU A 1
H1A H 0.2049 0.2916 0.6766 0.175 Uiso 0.66(2) 1 calc PR A 1
H1B H 0.0718 0.2623 0.7210 0.175 Uiso 0.66(2) 1 calc PR A 1
H1C H 0.1099 0.2272 0.6439 0.175 Uiso 0.66(2) 1 calc PR A 1
C2 C 0.2429(12) 0.1910(6) 0.7264(5) 0.069(3) Uani 0.66(2) 1 d PDU A 1
H2A H 0.3015 0.2145 0.7642 0.082 Uiso 0.66(2) 1 calc PR A 1
H2B H 0.1849 0.1523 0.7492 0.082 Uiso 0.66(2) 1 calc PR A 1
C1' C 0.218(3) 0.2691(11) 0.7119(11) 0.098(6) Uani 0.34(2) 1 d PDU A 2
H1'1 H 0.3093 0.2812 0.7332 0.147 Uiso 0.34(2) 1 calc PR A 2
H1'2 H 0.1426 0.2883 0.7429 0.147 Uiso 0.34(2) 1 calc PR A 2
H1'3 H 0.2106 0.2912 0.6635 0.147 Uiso 0.34(2) 1 calc PR A 2
C2' C 0.2033(18) 0.1857(12) 0.7056(15) 0.084(6) Uani 0.34(2) 1 d PDU A 2
H2'1 H 0.1955 0.1632 0.7543 0.101 Uiso 0.34(2) 1 calc PR A 2
H2'2 H 0.1185 0.1727 0.6772 0.101 Uiso 0.34(2) 1 calc PR A 2
C3 C 0.4176(2) 0.10428(12) 0.69189(12) 0.0479(6) Uani 1 1 d . A .
C4 C 0.5173(2) 0.08040(11) 0.63433(11) 0.0392(5) Uani 1 1 d . . .
C5 C 0.5980(2) 0.01796(11) 0.64309(12) 0.0448(5) Uani 1 1 d . . .
C6 C 0.6830(2) 0.02609(11) 0.52042(12) 0.0436(5) Uani 1 1 d . . .
C7 C 0.5172(2) 0.12708(10) 0.56356(11) 0.0381(5) Uani 1 1 d . . .
H7 H 0.4185 0.1310 0.5452 0.046 Uiso 1 1 calc R . .
C8 C 0.5784(2) 0.20549(10) 0.57276(10) 0.0367(5) Uani 1 1 d . . .
C9 C 0.7228(2) 0.21647(11) 0.58431(11) 0.0447(5) Uani 1 1 d . . .
H9 H 0.7853 0.1760 0.5871 0.054 Uiso 1 1 calc R . .
C10 C 0.7734(3) 0.28862(13) 0.59166(12) 0.0536(6) Uani 1 1 d . . .
H10 H 0.8713 0.2954 0.5992 0.064 Uiso 1 1 calc R . .
C11 C 0.5513(3) 0.33789(13) 0.57683(14) 0.0632(7) Uani 1 1 d . . .
H11 H 0.4913 0.3794 0.5739 0.076 Uiso 1 1 calc R . .
C12 C 0.4918(2) 0.26785(12) 0.56874(12) 0.0504(6) Uani 1 1 d . . .
H12 H 0.3937 0.2627 0.5606 0.060 Uiso 1 1 calc R . .
C13 C 0.6022(3) -0.03097(13) 0.71067(13) 0.0651(7) Uani 1 1 d . . .
H13A H 0.6496 -0.0049 0.7502 0.098 Uiso 1 1 calc R . .
H13B H 0.6537 -0.0761 0.6996 0.098 Uiso 1 1 calc R . .
H13C H 0.5060 -0.0432 0.7254 0.098 Uiso 1 1 calc R . .
N1 N 0.6841(2) -0.00828(10) 0.58683(11) 0.0524(5) Uani 1 1 d D . .
N2 N 0.7512(2) 0.00825(11) 0.45897(11) 0.0562(5) Uani 1 1 d . . .
N3 N 0.7100(2) 0.06147(12) 0.40898(11) 0.0606(6) Uani 1 1 d . . .
N4 N 0.6220(2) 0.10903(11) 0.43794(10) 0.0528(5) Uani 1 1 d . . .
N5 N 0.60345(17) 0.08638(9) 0.50919(9) 0.0410(4) Uani 1 1 d . . .
N6 N 0.6903(2) 0.34906(10) 0.58859(11) 0.0597(6) Uani 1 1 d . . .
O1 O 0.33317(17) 0.15942(9) 0.66794(9) 0.0621(5) Uani 1 1 d D . .
O2 O 0.4075(2) 0.07990(11) 0.75389(10) 0.0799(6) Uani 1 1 d . . .
O1W O 0.9878(3) 0.08148(18) 0.58925(14) 0.1171(9) Uani 1 1 d D . .
H1 H 0.731(2) -0.0532(11) 0.5891(13) 0.072(8) Uiso 1 1 d D . .
H1W H 1.073(4) 0.055(3) 0.574(2) 0.20(2) Uiso 1 1 d D . .
H2W H 0.980(5) 0.073(3) 0.6416(11) 0.20(2) Uiso 1 1 d 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
C1 C2 1.511(12) . ?
C1 H1A 0.9600 . ?
C1 H1B 0.9600 . ?
C1 H1C 0.9600 . ?
C2 O1 1.463(5) . ?
C2 H2A 0.9700 . ?
C2 H2B 0.9700 . ?
C1' C2' 1.500(18) . ?
C1' H1'1 0.9600 . ?
C1' H1'2 0.9600 . ?
C1' H1'3 0.9600 . ?
C2' O1 1.465(8) . ?
C2' H2'1 0.9700 . ?
C2' H2'2 0.9700 . ?
C3 O2 1.205(2) . ?
C3 O1 1.333(3) . ?
C3 C4 1.457(3) . ?
C4 C5 1.355(3) . ?
C4 C7 1.526(3) . ?
C5 N1 1.377(3) . ?
C5 C13 1.502(3) . ?
C6 N2 1.318(3) . ?
C6 N5 1.323(3) . ?
C6 N1 1.348(3) . ?
C7 N5 1.463(2) . ?
C7 C8 1.522(3) . ?
C7 H7 0.9800 . ?
C8 C9 1.375(3) . ?
C8 C12 1.378(3) . ?
C9 C10 1.379(3) . ?
C9 H9 0.9300 . ?
C10 N6 1.330(3) . ?
C10 H10 0.9300 . ?
C11 N6 1.327(3) . ?
C11 C12 1.377(3) . ?
C11 H11 0.9300 . ?
C12 H12 0.9300 . ?
C13 H13A 0.9600 . ?
C13 H13B 0.9600 . ?
C13 H13C 0.9600 . ?
N1 H1 0.917(16) . ?
N2 N3 1.366(3) . ?
N3 N4 1.291(3) . ?
N4 N5 1.360(2) . ?
O1W H1W 0.964(18) . ?
O1W H2W 0.961(19) . ?

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
O1 C2 C1 105.5(8) . . ?
O1 C2 H2A 110.6 . . ?
C1 C2 H2A 110.6 . . ?
O1 C2 H2B 110.6 . . ?
C1 C2 H2B 110.6 . . ?
H2A C2 H2B 108.8 . . ?
C2' C1' H1'1 109.5 . . ?
C2' C1' H1'2 109.5 . . ?
H1'1 C1' H1'2 109.5 . . ?
C2' C1' H1'3 109.5 . . ?
H1'1 C1' H1'3 109.5 . . ?
H1'2 C1' H1'3 109.5 . . ?
O1 C2' C1' 106.2(15) . . ?
O1 C2' H2'1 110.5 . . ?
C1' C2' H2'1 110.5 . . ?
O1 C2' H2'2 110.5 . . ?
C1' C2' H2'2 110.5 . . ?
H2'1 C2' H2'2 108.7 . . ?
O2 C3 O1 121.5(2) . . ?
O2 C3 C4 127.4(2) . . ?
O1 C3 C4 111.14(18) . . ?
C5 C4 C3 120.74(19) . . ?
C5 C4 C7 123.25(19) . . ?
C3 C4 C7 115.91(18) . . ?
C4 C5 N1 121.17(19) . . ?
C4 C5 C13 126.1(2) . . ?
N1 C5 C13 112.73(19) . . ?
N2 C6 N5 109.7(2) . . ?
N2 C6 N1 129.5(2) . . ?
N5 C6 N1 120.8(2) . . ?
N5 C7 C8 108.96(15) . . ?
N5 C7 C4 106.88(16) . . ?
C8 C7 C4 114.29(16) . . ?
N5 C7 H7 108.9 . . ?
C8 C7 H7 108.9 . . ?
C4 C7 H7 108.9 . . ?
C9 C8 C12 117.75(19) . . ?
C9 C8 C7 120.98(18) . . ?
C12 C8 C7 121.27(18) . . ?
C8 C9 C10 118.8(2) . . ?
C8 C9 H9 120.6 . . ?
C10 C9 H9 120.6 . . ?
N6 C10 C9 123.8(2) . . ?
N6 C10 H10 118.1 . . ?
C9 C10 H10 118.1 . . ?
N6 C11 C12 123.2(2) . . ?
N6 C11 H11 118.4 . . ?
C12 C11 H11 118.4 . . ?
C11 C12 C8 119.6(2) . . ?
C11 C12 H12 120.2 . . ?
C8 C12 H12 120.2 . . ?
C5 C13 H13A 109.5 . . ?
C5 C13 H13B 109.5 . . ?
H13A C13 H13B 109.5 . . ?
C5 C13 H13C 109.5 . . ?
H13A C13 H13C 109.5 . . ?
H13B C13 H13C 109.5 . . ?
C6 N1 C5 119.82(19) . . ?
C6 N1 H1 116.3(15) . . ?
C5 N1 H1 123.0(15) . . ?
C6 N2 N3 104.66(19) . . ?
N4 N3 N2 111.62(18) . . ?
N3 N4 N5 105.54(18) . . ?
C6 N5 N4 108.44(17) . . ?
C6 N5 C7 127.55(18) . . ?
N4 N5 C7 123.86(16) . . ?
C11 N6 C10 116.9(2) . . ?
C3 O1 C2 113.0(4) . . ?
C3 O1 C2' 125.0(12) . . ?
C2 O1 C2' 21.0(11) . . ?
H1W O1W H2W 106(2) . . ?

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
O2 C3 C4 C5 9.9(4) . . . . ?
O1 C3 C4 C5 -170.17(19) . . . . ?
O2 C3 C4 C7 -173.5(2) . . . . ?
O1 C3 C4 C7 6.4(3) . . . . ?
C3 C4 C5 N1 174.93(19) . . . . ?
C7 C4 C5 N1 -1.4(3) . . . . ?
C3 C4 C5 C13 -3.0(3) . . . . ?
C7 C4 C5 C13 -179.3(2) . . . . ?
C5 C4 C7 N5 6.5(3) . . . . ?
C3 C4 C7 N5 -169.97(16) . . . . ?
C5 C4 C7 C8 -114.1(2) . . . . ?
C3 C4 C7 C8 69.4(2) . . . . ?
N5 C7 C8 C9 -49.0(2) . . . . ?
C4 C7 C8 C9 70.5(2) . . . . ?
N5 C7 C8 C12 130.0(2) . . . . ?
C4 C7 C8 C12 -110.5(2) . . . . ?
C12 C8 C9 C10 0.4(3) . . . . ?
C7 C8 C9 C10 179.42(18) . . . . ?
C8 C9 C10 N6 0.3(3) . . . . ?
N6 C11 C12 C8 0.0(4) . . . . ?
C9 C8 C12 C11 -0.5(3) . . . . ?
C7 C8 C12 C11 -179.5(2) . . . . ?
N2 C6 N1 C5 -176.6(2) . . . . ?
N5 C6 N1 C5 2.2(3) . . . . ?
C4 C5 N1 C6 -3.6(3) . . . . ?
C13 C5 N1 C6 174.6(2) . . . . ?
N5 C6 N2 N3 0.4(2) . . . . ?
N1 C6 N2 N3 179.3(2) . . . . ?
C6 N2 N3 N4 0.0(2) . . . . ?
N2 N3 N4 N5 -0.4(2) . . . . ?
N2 C6 N5 N4 -0.7(2) . . . . ?
N1 C6 N5 N4 -179.68(18) . . . . ?
N2 C6 N5 C7 -176.43(17) . . . . ?
N1 C6 N5 C7 4.6(3) . . . . ?
N3 N4 N5 C6 0.7(2) . . . . ?
N3 N4 N5 C7 176.60(17) . . . . ?
C8 C7 N5 C6 115.7(2) . . . . ?
C4 C7 N5 C6 -8.3(3) . . . . ?
C8 C7 N5 N4 -59.4(2) . . . . ?
C4 C7 N5 N4 176.59(16) . . . . ?
C12 C11 N6 C10 0.7(4) . . . . ?
C9 C10 N6 C11 -0.8(3) . . . . ?
O2 C3 O1 C2 6.6(7) . . . . ?
C4 C3 O1 C2 -173.4(6) . . . . ?
O2 C3 O1 C2' -13.3(12) . . . . ?
C4 C3 O1 C2' 166.8(11) . . . . ?
C1 C2 O1 C3 -176.3(12) . . . . ?
C1 C2 O1 C2' -47(3) . . . . ?
C1' C2' O1 C3 129(2) . . . . ?
C1' C2' O1 C2 69(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
N1 H1 N6 0.917(16) 1.892(17) 2.805(3) 173(2) 7_755
O1W H1W N2 0.964(18) 2.077(19) 3.040(3) 176(4) 5_756
O1W H2W O2 0.961(19) 2.01(2) 2.931(3) 160(4) 6_657

_diffrn_measured_fraction_theta_max 0.999
_diffrn_reflns_theta_full        25.00
_diffrn_measured_fraction_theta_full 0.999
_refine_diff_density_max         0.185
_refine_diff_density_min         -0.205
_refine_diff_density_rms         0.036
_database_code_depnum_ccdc_archive 'CCDC 881461'
#######################################################################
#
#                 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_shelxl

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         
'(C28 H37 Cl2 N12 O4 Zn) * 2(C H4 O) * 0.5(H2 O)'
_chemical_formula_sum            'C28 H37 Cl2 N12 O6.50 Zn'
_chemical_formula_weight         781.97

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   C2/c

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                   10.4600(4)
_cell_length_b                   13.5070(5)
_cell_length_c                   26.6520(9)
_cell_angle_alpha                90.00
_cell_angle_beta                 93.851(2)
_cell_angle_gamma                90.00
_cell_volume                     3757.0(2)
_cell_formula_units_Z            4
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    2119
_cell_measurement_theta_min      2.5
_cell_measurement_theta_max      20.0

_exptl_crystal_description       block
_exptl_crystal_colour            brown
_exptl_crystal_size_max          0.30
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.20
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.382
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1620
_exptl_absorpt_coefficient_mu    0.853
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.721
_exptl_absorpt_correction_T_max  0.834
_exptl_absorpt_process_details   'SADABS (Bruker, 1999)'

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      293(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 axs kappa apex2 CCD Diffractometer'
_diffrn_measurement_method       'ω and φ scan'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        0
_diffrn_reflns_number            11512
_diffrn_reflns_av_R_equivalents  0.1363
_diffrn_reflns_av_sigmaI/netI    0.2575
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_l_min       -29
_diffrn_reflns_limit_l_max       29
_diffrn_reflns_theta_min         2.47
_diffrn_reflns_theta_max         23.58
_reflns_number_total             2751
_reflns_number_gt                1308
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'APEX2 (Bruker, 2004)'
_computing_cell_refinement       'APEX2/SAINT (Bruker, 2004)'
_computing_data_reduction        'SAINT/XPREP (Bruker, 2004)'
_computing_structure_solution    'SIR92 (Altornare et al., 1993)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_molecular_graphics    
'ORTEP3 (Farrugia, 1997) and Mercury (Bruno et al., 2002)'
_computing_publication_material  'SHELXL-97 (Sheldrick, 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 > 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)+(0.0924P)²+0.0000P] 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         2751
_refine_ls_number_parameters     281
_refine_ls_number_restraints     61
_refine_ls_R_factor_all          0.1965
_refine_ls_R_factor_gt           0.0621
_refine_ls_wR_factor_ref         0.1873
_refine_ls_wR_factor_gt          0.1518
_refine_ls_goodness_of_fit_ref   0.971
_refine_ls_restrained_S_all      0.968
_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
H6A H 1.475(3) 0.605(5) 0.026(2) 0.08(2) Uiso 1 1 d D . .
C1 C 0.9579(7) 0.4668(5) 0.1554(3) 0.073(2) Uani 1 1 d . . .
H1 H 0.8752 0.4428 0.1578 0.088 Uiso 1 1 calc R . .
C2 C 0.9853(6) 0.5185(5) 0.1136(2) 0.073(2) Uani 1 1 d . . .
H2 H 0.9221 0.5292 0.0880 0.087 Uiso 1 1 calc R . .
C3 C 1.1063(5) 0.5546(5) 0.1096(2) 0.0525(16) Uani 1 1 d . . .
C4 C 1.1926(6) 0.5426(5) 0.1480(3) 0.072(2) Uani 1 1 d . . .
H4 H 1.2738 0.5702 0.1469 0.087 Uiso 1 1 calc R . .
C5 C 1.1611(6) 0.4887(6) 0.1901(2) 0.078(2) Uani 1 1 d . . .
H5 H 1.2224 0.4799 0.2167 0.093 Uiso 1 1 calc R . .
C6 C 1.1398(5) 0.6027(5) 0.0598(2) 0.0569(17) Uani 1 1 d . . .
H6 H 1.0610 0.6248 0.0412 0.068 Uiso 1 1 calc R . .
C7 C 1.3251(6) 0.5269(6) 0.0220(2) 0.0611(18) Uani 1 1 d . . .
C8 C 1.3546(6) 0.6839(6) 0.0560(2) 0.0663(19) Uani 1 1 d . . .
C9 C 1.2318(6) 0.6884(5) 0.0663(2) 0.0626(18) Uani 1 1 d . . .
C10 C 1.4549(6) 0.7630(5) 0.0642(3) 0.090(2) Uani 1 1 d . . .
H10A H 1.4186 0.8261 0.0546 0.134 Uiso 1 1 calc R . .
H10B H 1.5255 0.7488 0.0441 0.134 Uiso 1 1 calc R . .
H10C H 1.4845 0.7646 0.0991 0.134 Uiso 1 1 calc R . .
C11 C 1.1736(8) 0.7775(7) 0.0834(3) 0.080(2) Uani 1 1 d . A .
C12 C 0.991(2) 0.8453(13) 0.1146(9) 0.120(6) Uani 0.727(17) 1 d PDU A 3
H12A H 0.9936 0.9013 0.0919 0.144 Uiso 0.727(17) 1 calc PR A 3
H12B H 1.0276 0.8646 0.1476 0.144 Uiso 0.727(17) 1 calc PR A 3
C13 C 0.8562(13) 0.8039(12) 0.1168(7) 0.160(7) Uani 0.727(17) 1 d PDU A 3
H13A H 0.8314 0.7711 0.0857 0.240 Uiso 0.727(17) 1 calc PR A 3
H13B H 0.7977 0.8571 0.1221 0.240 Uiso 0.727(17) 1 calc PR A 3
H13C H 0.8545 0.7575 0.1441 0.240 Uiso 0.727(17) 1 calc PR A 3
O4 O 1.0000 0.695(3) 0.2500 0.160(14) Uani 0.297(17) 2 d SPU B 3
C12' C 0.969(6) 0.826(4) 0.1191(19) 0.123(11) Uani 0.273(17) 1 d PDU A 4
H12C H 0.8854 0.8215 0.1014 0.147 Uiso 0.273(17) 1 calc PR A 4
H12D H 0.9992 0.8936 0.1162 0.147 Uiso 0.273(17) 1 calc PR A 4
C13' C 0.957(4) 0.802(3) 0.1744(17) 0.176(16) Uani 0.273(17) 1 d PDU A 4
H13D H 1.0344 0.8211 0.1935 0.265 Uiso 0.273(17) 1 calc PR A 4
H13E H 0.9442 0.7318 0.1781 0.265 Uiso 0.273(17) 1 calc PR A 4
H13F H 0.8858 0.8370 0.1864 0.265 Uiso 0.273(17) 1 calc PR A 4
N1 N 1.0448(5) 0.4493(4) 0.19296(19) 0.0605(14) Uani 1 1 d . . .
N2 N 1.2021(4) 0.5274(4) 0.03073(17) 0.0562(14) Uani 1 1 d . . .
N3 N 1.1459(5) 0.4452(4) 0.0118(2) 0.0671(15) Uani 1 1 d . . .
N4 N 1.2334(5) 0.3953(4) -0.0087(2) 0.0759(17) Uani 1 1 d . . .
N5 N 1.3476(5) 0.4462(5) -0.0032(2) 0.0753(17) Uani 1 1 d . . .
N6 N 1.4024(5) 0.6001(5) 0.0363(2) 0.0757(18) Uani 1 1 d D . .
O1 O 1.2231(5) 0.8581(4) 0.0865(2) 0.1084(18) Uani 1 1 d . . .
O2 O 1.0554(5) 0.7612(4) 0.0958(2) 0.0924(16) Uani 1 1 d D . .
Cl1 Cl 0.8286(2) 0.27640(19) 0.22238(9) 0.1257(10) Uani 1 1 d . . .
Zn1 Zn 1.0000 0.35884(9) 0.2500 0.0767(5) Uani 1 2 d S . .
C14 C 0.860(3) 0.090(4) 0.3485(15) 0.217(12) Uani 0.57(2) 1 d PDU C -5
O3 O 0.9862(17) 0.0999(17) 0.3330(9) 0.241(11) Uani 0.57(2) 1 d PDU C -5
O4' O 1.031(8) 0.783(4) 0.250(6) 0.152(16) Uani 0.102(8) 1 d PU D -5
C14' C 0.936(4) 0.041(3) 0.2823(19) 0.271(14) Uani 0.43(2) 1 d PDU C -6
O3' O 0.845(3) 0.086(3) 0.3145(16) 0.243(12) Uani 0.43(2) 1 d PDU C -6


_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
C1 N1 1.326(8) . ?
C1 C2 1.363(9) . ?
C1 H1 0.9300 . ?
C2 C3 1.367(7) . ?
C2 H2 0.9300 . ?
C3 C4 1.329(8) . ?
C3 C6 1.538(8) . ?
C4 C5 1.395(9) . ?
C4 H4 0.9300 . ?
C5 N1 1.335(7) . ?
C5 H5 0.9300 . ?
C6 N2 1.460(7) . ?
C6 C9 1.508(8) . ?
C6 H6 0.9800 . ?
C7 N5 1.309(8) . ?
C7 N6 1.318(8) . ?
C7 N2 1.322(7) . ?
C8 C9 1.332(8) . ?
C8 N6 1.358(8) . ?
C8 C10 1.503(8) . ?
C9 C11 1.437(10) . ?
C10 H10A 0.9600 . ?
C10 H10B 0.9600 . ?
C10 H10C 0.9600 . ?
C11 O1 1.206(8) . ?
C11 O2 1.320(8) . ?
C12 O2 1.427(12) . ?
C12 C13 1.526(19) . ?
C12 H12A 0.9700 . ?
C12 H12B 0.9700 . ?
C13 H13A 0.9600 . ?
C13 H13B 0.9600 . ?
C13 H13C 0.9600 . ?
C12' O2 1.427(19) . ?
C12' C13' 1.52(2) . ?
C12' H12C 0.9700 . ?
C12' H12D 0.9700 . ?
C13' H13D 0.9600 . ?
C13' H13E 0.9600 . ?
C13' H13F 0.9600 . ?
N1 Zn1 2.030(5) . ?
N2 N3 1.339(6) . ?
N3 N4 1.288(7) . ?
N4 N5 1.377(7) . ?
N6 H6A 0.83(2) . ?
Cl1 Zn1 2.195(2) . ?
Zn1 N1 2.030(5) 2_755 ?
Zn1 Cl1 2.195(2) 2_755 ?
C14 O3 1.414(19) . ?
C14' O3' 1.45(2) . ?

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 122.5(6) . . ?
N1 C1 H1 118.8 . . ?
C2 C1 H1 118.8 . . ?
C1 C2 C3 119.6(7) . . ?
C1 C2 H2 120.2 . . ?
C3 C2 H2 120.2 . . ?
C4 C3 C2 118.7(6) . . ?
C4 C3 C6 122.3(5) . . ?
C2 C3 C6 119.0(6) . . ?
C3 C4 C5 119.9(6) . . ?
C3 C4 H4 120.0 . . ?
C5 C4 H4 120.0 . . ?
N1 C5 C4 121.3(6) . . ?
N1 C5 H5 119.4 . . ?
C4 C5 H5 119.4 . . ?
N2 C6 C9 106.9(5) . . ?
N2 C6 C3 107.4(5) . . ?
C9 C6 C3 114.0(5) . . ?
N2 C6 H6 109.5 . . ?
C9 C6 H6 109.5 . . ?
C3 C6 H6 109.5 . . ?
N5 C7 N6 130.1(6) . . ?
N5 C7 N2 107.8(6) . . ?
N6 C7 N2 122.0(7) . . ?
C9 C8 N6 120.2(6) . . ?
C9 C8 C10 127.7(7) . . ?
N6 C8 C10 112.1(6) . . ?
C8 C9 C11 122.6(6) . . ?
C8 C9 C6 123.9(7) . . ?
C11 C9 C6 113.5(6) . . ?
C8 C10 H10A 109.5 . . ?
C8 C10 H10B 109.5 . . ?
H10A C10 H10B 109.5 . . ?
C8 C10 H10C 109.5 . . ?
H10A C10 H10C 109.5 . . ?
H10B C10 H10C 109.5 . . ?
O1 C11 O2 122.5(8) . . ?
O1 C11 C9 126.1(7) . . ?
O2 C11 C9 111.4(7) . . ?
O2 C12 C13 100.3(13) . . ?
O2 C12 H12A 111.7 . . ?
C13 C12 H12A 111.7 . . ?
O2 C12 H12B 111.7 . . ?
C13 C12 H12B 111.7 . . ?
H12A C12 H12B 109.5 . . ?
C12 C13 H13A 109.5 . . ?
C12 C13 H13B 109.5 . . ?
H13A C13 H13B 109.5 . . ?
C12 C13 H13C 109.5 . . ?
H13A C13 H13C 109.5 . . ?
H13B C13 H13C 109.5 . . ?
O2 C12' C13' 113(3) . . ?
O2 C12' H12C 109.1 . . ?
C13' C12' H12C 109.1 . . ?
O2 C12' H12D 109.1 . . ?
C13' C12' H12D 109.1 . . ?
H12C C12' H12D 107.8 . . ?
C12' C13' H13D 109.5 . . ?
C12' C13' H13E 109.5 . . ?
H13D C13' H13E 109.5 . . ?
C12' C13' H13F 109.5 . . ?
H13D C13' H13F 109.5 . . ?
H13E C13' H13F 109.5 . . ?
C1 N1 C5 117.9(5) . . ?
C1 N1 Zn1 119.4(4) . . ?
C5 N1 Zn1 122.7(5) . . ?
C7 N2 N3 109.7(5) . . ?
C7 N2 C6 124.9(6) . . ?
N3 N2 C6 125.3(4) . . ?
N4 N3 N2 106.7(5) . . ?
N3 N4 N5 109.2(5) . . ?
C7 N5 N4 106.6(5) . . ?
C7 N6 C8 120.2(5) . . ?
C7 N6 H6A 122(5) . . ?
C8 N6 H6A 115(5) . . ?
C11 O2 C12 115.1(11) . . ?
C11 O2 C12' 129(3) . . ?
C12 O2 C12' 15(4) . . ?
N1 Zn1 N1 106.0(3) . 2_755 ?
N1 Zn1 Cl1 106.18(18) . . ?
N1 Zn1 Cl1 109.40(17) 2_755 . ?
N1 Zn1 Cl1 109.41(17) . 2_755 ?
N1 Zn1 Cl1 106.18(18) 2_755 2_755 ?
Cl1 Zn1 Cl1 119.03(15) . 2_755 ?

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
N1 C1 C2 C3 -0.2(11) . . . . ?
C1 C2 C3 C4 -3.6(10) . . . . ?
C1 C2 C3 C6 173.3(6) . . . . ?
C2 C3 C4 C5 4.0(10) . . . . ?
C6 C3 C4 C5 -172.8(6) . . . . ?
C3 C4 C5 N1 -0.8(11) . . . . ?
C4 C3 C6 N2 80.1(7) . . . . ?
C2 C3 C6 N2 -96.7(7) . . . . ?
C4 C3 C6 C9 -38.2(9) . . . . ?
C2 C3 C6 C9 145.0(6) . . . . ?
N6 C8 C9 C11 -175.0(6) . . . . ?
C10 C8 C9 C11 5.7(10) . . . . ?
N6 C8 C9 C6 3.3(9) . . . . ?
C10 C8 C9 C6 -175.9(6) . . . . ?
N2 C6 C9 C8 -12.6(8) . . . . ?
C3 C6 C9 C8 105.9(7) . . . . ?
N2 C6 C9 C11 165.9(5) . . . . ?
C3 C6 C9 C11 -75.6(7) . . . . ?
C8 C9 C11 O1 6.6(12) . . . . ?
C6 C9 C11 O1 -171.9(7) . . . . ?
C8 C9 C11 O2 -173.7(6) . . . . ?
C6 C9 C11 O2 7.8(8) . . . . ?
C2 C1 N1 C5 3.4(10) . . . . ?
C2 C1 N1 Zn1 -173.3(5) . . . . ?
C4 C5 N1 C1 -2.9(10) . . . . ?
C4 C5 N1 Zn1 173.6(5) . . . . ?
N5 C7 N2 N3 1.2(7) . . . . ?
N6 C7 N2 N3 179.3(6) . . . . ?
N5 C7 N2 C6 177.1(5) . . . . ?
N6 C7 N2 C6 -4.9(9) . . . . ?
C9 C6 N2 C7 13.4(8) . . . . ?
C3 C6 N2 C7 -109.3(6) . . . . ?
C9 C6 N2 N3 -171.3(5) . . . . ?
C3 C6 N2 N3 65.9(7) . . . . ?
C7 N2 N3 N4 -0.5(6) . . . . ?
C6 N2 N3 N4 -176.4(5) . . . . ?
N2 N3 N4 N5 -0.3(7) . . . . ?
N6 C7 N5 N4 -179.2(7) . . . . ?
N2 C7 N5 N4 -1.3(7) . . . . ?
N3 N4 N5 C7 1.0(7) . . . . ?
N5 C7 N6 C8 170.6(7) . . . . ?
N2 C7 N6 C8 -7.0(9) . . . . ?
C9 C8 N6 C7 7.6(9) . . . . ?
C10 C8 N6 C7 -173.1(6) . . . . ?
O1 C11 O2 C12 -1.9(15) . . . . ?
C9 C11 O2 C12 178.3(12) . . . . ?
O1 C11 O2 C12' -7(3) . . . . ?
C9 C11 O2 C12' 173(3) . . . . ?
C13 C12 O2 C11 171.7(10) . . . . ?
C13 C12 O2 C12' -24(12) . . . . ?
C13' C12' O2 C11 -104(5) . . . . ?
C13' C12' O2 C12 -123(17) . . . . ?
C1 N1 Zn1 N1 -99.8(5) . . . 2_755 ?
C5 N1 Zn1 N1 83.8(5) . . . 2_755 ?
C1 N1 Zn1 Cl1 16.5(5) . . . . ?
C5 N1 Zn1 Cl1 -160.0(5) . . . . ?
C1 N1 Zn1 Cl1 146.2(5) . . . 2_755 ?
C5 N1 Zn1 Cl1 -30.3(5) . . . 2_755 ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
C1 H1 O1 0.93 2.65 3.310(10) 128.2 3_445
C1 H1 Cl1 0.93 2.89 3.456(7) 120.3 .
C4 H4 O3 0.93 2.56 3.452(19) 160.1 4_755
C6 H6 N3 0.98 2.68 3.497(8) 141.6 5_765
C10 H10A O1 0.96 2.31 2.842(9) 114.3 .

_diffrn_measured_fraction_theta_max 0.975
_diffrn_reflns_theta_full        23.58
_diffrn_measured_fraction_theta_full 0.975
_refine_diff_density_max         0.468
_refine_diff_density_min         -0.306
_refine_diff_density_rms         0.081
_database_code_depnum_ccdc_archive 'CCDC 873831'
