# Electronic Supplementary Material (ESI) for CrystEngComm.
# 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_HInMe_2_py

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
 ?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C15 H10 N2 O4'
_chemical_formula_weight         282.25

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'

_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, y+1/2, -z+1/2'
'x+1/2, -y+1/2, -z'
'-x, -y, -z'
'x-1/2, y, -z-1/2'
'x, -y-1/2, z-1/2'
'-x-1/2, y-1/2, z'

_cell_length_a                   13.5187(7)
_cell_length_b                   7.2436(4)
_cell_length_c                   26.014(3)
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_volume                     2547.4(4)
_cell_formula_units_Z            8
_cell_measurement_temperature    150(2)
_cell_measurement_reflns_used    1037
_cell_measurement_theta_min      2.8064
_cell_measurement_theta_max      29.1621

_exptl_crystal_description       plate
_exptl_crystal_colour            colorless
_exptl_crystal_size_max          0.58
_exptl_crystal_size_mid          0.48
_exptl_crystal_size_min          0.02
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.472
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1168
_exptl_absorpt_coefficient_mu    0.109
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.96705
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_process_details   
;
CrysAlisPro, Agilent Technologies,
Version 1.171.35.19 (release 27-10-2011 CrysAlis171 .NET)
(compiled Oct 27 2011,15:02:11)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;

_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      150(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'Enhance (Mo) X-ray Source'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Xcalibur, Sapphire3, Gemini'
_diffrn_measurement_method       ?
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            7391
_diffrn_reflns_av_R_equivalents  0.0465
_diffrn_reflns_av_sigmaI/netI    0.0644
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_h_max       18
_diffrn_reflns_limit_k_min       -4
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_l_min       -32
_diffrn_reflns_limit_l_max       33
_diffrn_reflns_theta_min         3.01
_diffrn_reflns_theta_max         29.23
_reflns_number_total             2982
_reflns_number_gt                1992
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.35.19 (release 27-10-2011 CrysAlis171 .NET)
(compiled Oct 27 2011,15:02:11)
;
_computing_cell_refinement       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.35.19 (release 27-10-2011 CrysAlis171 .NET)
(compiled Oct 27 2011,15:02:11)
;
_computing_data_reduction        
;
CrysAlisPro, Agilent Technologies,
Version 1.171.35.19 (release 27-10-2011 CrysAlis171 .NET)
(compiled Oct 27 2011,15:02:11)
;
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    ?
_computing_publication_material  ?

_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)+(0.0349P)²+4.1647P] 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         2982
_refine_ls_number_parameters     191
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1201
_refine_ls_R_factor_gt           0.0779
_refine_ls_wR_factor_ref         0.1613
_refine_ls_wR_factor_gt          0.1443
_refine_ls_goodness_of_fit_ref   1.091
_refine_ls_restrained_S_all      1.091
_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
C1 C 0.7114(2) 0.9246(4) 0.64655(12) 0.0227(6) Uani 1 1 d . . .
C2 C 0.5558(2) 0.7920(4) 0.65362(12) 0.0251(7) Uani 1 1 d . . .
C3 C 0.5946(2) 0.8255(4) 0.70651(12) 0.0230(7) Uani 1 1 d . . .
C4 C 0.5530(2) 0.7875(4) 0.75386(12) 0.0237(7) Uani 1 1 d . . .
H4 H 0.4899 0.7372 0.7565 0.028 Uiso 1 1 calc R . .
C5 C 0.6091(2) 0.8271(4) 0.79777(12) 0.0258(7) Uani 1 1 d . . .
C6 C 0.7037(2) 0.9032(5) 0.79334(12) 0.0307(8) Uani 1 1 d . . .
H6 H 0.7400 0.9288 0.8229 0.037 Uiso 1 1 calc R . .
C7 C 0.7444(2) 0.9411(4) 0.74525(12) 0.0293(7) Uani 1 1 d . . .
H7 H 0.8075 0.9911 0.7422 0.035 Uiso 1 1 calc R . .
C8 C 0.6883(2) 0.9022(4) 0.70234(12) 0.0228(7) Uani 1 1 d . . .
C9 C 0.5704(2) 0.7861(4) 0.85058(12) 0.0270(7) Uani 1 1 d . . .
C10 C 0.6259(2) 0.8348(4) 0.56483(11) 0.0239(7) Uani 1 1 d . . .
H10A H 0.5681 0.7618 0.5561 0.029 Uiso 1 1 calc R . .
H10B H 0.6839 0.7653 0.5544 0.029 Uiso 1 1 calc R . .
C11 C 0.6226(2) 1.0128(4) 0.53446(11) 0.0194(6) Uani 1 1 d . . .
C12 C 0.6497(2) 1.0133(5) 0.48288(12) 0.0291(8) Uani 1 1 d . . .
H12 H 0.6692 0.9046 0.4668 0.035 Uiso 1 1 calc R . .
C13 C 0.6473(2) 1.1765(6) 0.45584(13) 0.0384(9) Uani 1 1 d . . .
H13 H 0.6657 1.1796 0.4214 0.046 Uiso 1 1 calc R . .
C14 C 0.6173(2) 1.3348(5) 0.48035(14) 0.0351(9) Uani 1 1 d . . .
H14 H 0.6155 1.4469 0.4629 0.042 Uiso 1 1 calc R . .
C15 C 0.5899(2) 1.3243(4) 0.53128(13) 0.0301(8) Uani 1 1 d . . .
H15 H 0.5692 1.4314 0.5478 0.036 Uiso 1 1 calc R . .
N1 N 0.62876(18) 0.8595(3) 0.62011(9) 0.0217(6) Uani 1 1 d . . .
N2 N 0.59187(18) 1.1652(3) 0.55827(10) 0.0237(6) Uani 1 1 d . . .
O1 O 0.78499(15) 0.9853(3) 0.62629(8) 0.0303(5) Uani 1 1 d . . .
O2 O 0.47907(16) 0.7215(4) 0.64046(9) 0.0377(6) Uani 1 1 d . . .
O3 O 0.47992(17) 0.7182(4) 0.84946(9) 0.0371(6) Uani 1 1 d . . .
H3 H 0.4617 0.6954 0.8788 0.056 Uiso 1 1 calc R . .
O4 O 0.61901(17) 0.8115(3) 0.88942(9) 0.0368(6) 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
C1 O1 1.208(3) . ?
C1 N1 1.395(4) . ?
C1 C8 1.494(4) . ?
C2 O2 1.205(4) . ?
C2 N1 1.405(4) . ?
C2 C3 1.493(4) . ?
C3 C4 1.381(4) . ?
C3 C8 1.387(4) . ?
C4 C5 1.401(4) . ?
C4 H4 0.9300 . ?
C5 C6 1.397(4) . ?
C5 C9 1.500(4) . ?
C6 C7 1.394(4) . ?
C6 H6 0.9300 . ?
C7 C8 1.379(4) . ?
C7 H7 0.9300 . ?
C9 O4 1.219(4) . ?
C9 O3 1.319(4) . ?
C10 N1 1.450(4) . ?
C10 C11 1.513(4) . ?
C10 H10A 0.9700 . ?
C10 H10B 0.9700 . ?
C11 N2 1.332(4) . ?
C11 C12 1.391(4) . ?
C12 C13 1.376(5) . ?
C12 H12 0.9300 . ?
C13 C14 1.373(5) . ?
C13 H13 0.9300 . ?
C14 C15 1.378(5) . ?
C14 H14 0.9300 . ?
C15 N2 1.350(4) . ?
C15 H15 0.9300 . ?
O3 H3 0.8200 . ?

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 C1 N1 124.6(3) . . ?
O1 C1 C8 129.5(3) . . ?
N1 C1 C8 105.9(2) . . ?
O2 C2 N1 125.1(3) . . ?
O2 C2 C3 129.3(3) . . ?
N1 C2 C3 105.6(3) . . ?
C4 C3 C8 121.4(3) . . ?
C4 C3 C2 130.3(3) . . ?
C8 C3 C2 108.3(3) . . ?
C3 C4 C5 117.8(3) . . ?
C3 C4 H4 121.1 . . ?
C5 C4 H4 121.1 . . ?
C6 C5 C4 120.6(3) . . ?
C6 C5 C9 118.2(3) . . ?
C4 C5 C9 121.2(3) . . ?
C7 C6 C5 120.9(3) . . ?
C7 C6 H6 119.6 . . ?
C5 C6 H6 119.6 . . ?
C8 C7 C6 118.0(3) . . ?
C8 C7 H7 121.0 . . ?
C6 C7 H7 121.0 . . ?
C7 C8 C3 121.4(3) . . ?
C7 C8 C1 130.5(3) . . ?
C3 C8 C1 108.1(3) . . ?
O4 C9 O3 125.0(3) . . ?
O4 C9 C5 122.8(3) . . ?
O3 C9 C5 112.1(3) . . ?
N1 C10 C11 114.4(2) . . ?
N1 C10 H10A 108.6 . . ?
C11 C10 H10A 108.6 . . ?
N1 C10 H10B 108.6 . . ?
C11 C10 H10B 108.6 . . ?
H10A C10 H10B 107.6 . . ?
N2 C11 C12 121.9(3) . . ?
N2 C11 C10 118.2(3) . . ?
C12 C11 C10 119.9(3) . . ?
C13 C12 C11 119.3(3) . . ?
C13 C12 H12 120.4 . . ?
C11 C12 H12 120.4 . . ?
C14 C13 C12 119.2(3) . . ?
C14 C13 H13 120.4 . . ?
C12 C13 H13 120.4 . . ?
C13 C14 C15 118.6(3) . . ?
C13 C14 H14 120.7 . . ?
C15 C14 H14 120.7 . . ?
N2 C15 C14 122.8(3) . . ?
N2 C15 H15 118.6 . . ?
C14 C15 H15 118.6 . . ?
C1 N1 C2 112.0(2) . . ?
C1 N1 C10 123.5(2) . . ?
C2 N1 C10 123.6(3) . . ?
C11 N2 C15 118.1(3) . . ?
C9 O3 H3 109.5 . . ?

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 C2 C3 C4 -1.0(6) . . . . ?
N1 C2 C3 C4 179.5(3) . . . . ?
O2 C2 C3 C8 177.1(3) . . . . ?
N1 C2 C3 C8 -2.4(3) . . . . ?
C8 C3 C4 C5 -0.7(4) . . . . ?
C2 C3 C4 C5 177.2(3) . . . . ?
C3 C4 C5 C6 0.2(4) . . . . ?
C3 C4 C5 C9 -178.6(3) . . . . ?
C4 C5 C6 C7 -0.1(5) . . . . ?
C9 C5 C6 C7 178.8(3) . . . . ?
C5 C6 C7 C8 0.4(5) . . . . ?
C6 C7 C8 C3 -0.8(5) . . . . ?
C6 C7 C8 C1 -179.1(3) . . . . ?
C4 C3 C8 C7 1.0(5) . . . . ?
C2 C3 C8 C7 -177.3(3) . . . . ?
C4 C3 C8 C1 179.7(3) . . . . ?
C2 C3 C8 C1 1.4(3) . . . . ?
O1 C1 C8 C7 -1.3(6) . . . . ?
N1 C1 C8 C7 178.7(3) . . . . ?
O1 C1 C8 C3 -179.7(3) . . . . ?
N1 C1 C8 C3 0.2(3) . . . . ?
C6 C5 C9 O4 -2.1(5) . . . . ?
C4 C5 C9 O4 176.7(3) . . . . ?
C6 C5 C9 O3 178.8(3) . . . . ?
C4 C5 C9 O3 -2.3(4) . . . . ?
N1 C10 C11 N2 -20.7(4) . . . . ?
N1 C10 C11 C12 160.4(3) . . . . ?
N2 C11 C12 C13 1.8(4) . . . . ?
C10 C11 C12 C13 -179.4(3) . . . . ?
C11 C12 C13 C14 -0.6(5) . . . . ?
C12 C13 C14 C15 -0.5(5) . . . . ?
C13 C14 C15 N2 0.5(5) . . . . ?
O1 C1 N1 C2 178.1(3) . . . . ?
C8 C1 N1 C2 -1.8(3) . . . . ?
O1 C1 N1 C10 8.1(5) . . . . ?
C8 C1 N1 C10 -171.8(2) . . . . ?
O2 C2 N1 C1 -176.9(3) . . . . ?
C3 C2 N1 C1 2.6(3) . . . . ?
O2 C2 N1 C10 -7.0(5) . . . . ?
C3 C2 N1 C10 172.6(2) . . . . ?
C11 C10 N1 C1 -71.9(4) . . . . ?
C11 C10 N1 C2 119.3(3) . . . . ?
C12 C11 N2 C15 -1.8(4) . . . . ?
C10 C11 N2 C15 179.4(3) . . . . ?
C14 C15 N2 C11 0.7(4) . . . . ?

_diffrn_measured_fraction_theta_max 0.864
_diffrn_reflns_theta_full        26.00
_diffrn_measured_fraction_theta_full 0.999
_refine_diff_density_max         0.294
_refine_diff_density_min         -0.233
_refine_diff_density_rms         0.062
_database_code_depnum_ccdc_archive 'CCDC 973184'
#######################################################################
#
#                 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_cpd_1

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
 ?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         
'C30 H18 N4 O8 Zn, C2 H4 O0.5, C0.5 H2O0.5, H0.5 O0.25'
_chemical_formula_sum            'C32.50 H24.50 N4 O9.25 Zn'
_chemical_formula_weight         684.43

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   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                   22.3598(7)
_cell_length_b                   15.1429(4)
_cell_length_c                   23.0395(7)
_cell_angle_alpha                90.00
_cell_angle_beta                 110.657(4)
_cell_angle_gamma                90.00
_cell_volume                     7299.5(4)
_cell_formula_units_Z            8
_cell_measurement_temperature    150(2)
_cell_measurement_reflns_used    4874
_cell_measurement_theta_min      2.7559
_cell_measurement_theta_max      29.1159

_exptl_crystal_description       prism
_exptl_crystal_colour            pale-yellow
_exptl_crystal_size_max          0.66
_exptl_crystal_size_mid          0.25
_exptl_crystal_size_min          0.18
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.246
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             2812
_exptl_absorpt_coefficient_mu    0.726
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.97368
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_process_details   
;
CrysAlisPro, Agilent Technologies,
Version 1.171.35.19 (release 27-10-2011 CrysAlis171 .NET)
(compiled Oct 27 2011,15:02:11)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;

_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      150(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'Enhance (Mo) X-ray Source'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Xcalibur, Sapphire3, Gemini'
_diffrn_measurement_method       ?
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            16545
_diffrn_reflns_av_R_equivalents  0.0271
_diffrn_reflns_av_sigmaI/netI    0.0556
_diffrn_reflns_limit_h_min       -29
_diffrn_reflns_limit_h_max       30
_diffrn_reflns_limit_k_min       -20
_diffrn_reflns_limit_k_max       19
_diffrn_reflns_limit_l_min       -29
_diffrn_reflns_limit_l_max       30
_diffrn_reflns_theta_min         2.76
_diffrn_reflns_theta_max         29.18
_reflns_number_total             8370
_reflns_number_gt                6524
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.35.19 (release 27-10-2011 CrysAlis171 .NET)
(compiled Oct 27 2011,15:02:11)
;
_computing_cell_refinement       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.35.19 (release 27-10-2011 CrysAlis171 .NET)
(compiled Oct 27 2011,15:02:11)
;
_computing_data_reduction        
;
CrysAlisPro, Agilent Technologies,
Version 1.171.35.19 (release 27-10-2011 CrysAlis171 .NET)
(compiled Oct 27 2011,15:02:11)
;
_computing_structure_solution    'SIR92 (Giacovazzo et al, 1993)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    ?
_computing_publication_material  ?

_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. SADI routine was applied to 
 make the lattice THF molecule to be a more reliable model, which was 
 refined isotropically with site occupancy factor of 0.5. Except THF molecule, 
 attempts to locate and reasonably model the other highly disordered solvent 
 molecules in the voids were unsuccessful. Therefore, the SQUEEZE routine of 
 PLATON was used to remove the diffraction contribution from these solvents 
 to produce a set of solvent free diffraction intensities. The calculations 
 indicate the presence of 87 e/unit cell which are attributed to four 
 methanol molecules and two water molecules per cell and then included in 
 Dcalc, F000, and molecular weight.
;

_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)+(0.1095P)²+6.9778P] 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         8370
_refine_ls_number_parameters     408
_refine_ls_number_restraints     4
_refine_ls_R_factor_all          0.0744
_refine_ls_R_factor_gt           0.0578
_refine_ls_wR_factor_ref         0.1867
_refine_ls_wR_factor_gt          0.1737
_refine_ls_goodness_of_fit_ref   1.072
_refine_ls_restrained_S_all      1.073
_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 0.287526(16) 0.33316(2) 0.021943(14) 0.01535(13) Uani 1 1 d . . .
N1 N 0.26364(13) 0.54976(19) 0.15607(12) 0.0232(6) Uani 1 1 d . . .
N2 N 0.33879(12) 0.44574(18) 0.05440(11) 0.0196(5) Uani 1 1 d . . .
N3 N 0.55355(15) -0.1309(2) 0.08593(15) 0.0340(7) Uani 1 1 d . . .
N4 N 0.57369(17) -0.3631(2) 0.12455(18) 0.0449(9) Uani 1 1 d . . .
O1 O 0.19836(15) 0.65345(19) 0.09022(11) 0.0403(7) Uani 1 1 d . . .
O2 O 0.31191(12) 0.46163(16) 0.24237(11) 0.0309(6) Uani 1 1 d . . .
O3 O 0.28252(12) 0.65787(16) 0.43212(10) 0.0279(5) Uani 1 1 d . . .
O4 O 0.22453(12) 0.78028(16) 0.40180(10) 0.0275(5) Uani 1 1 d . . .
O5 O 0.64043(13) -0.0387(2) 0.13001(18) 0.0566(9) Uani 1 1 d . . .
O6 O 0.45055(15) -0.18470(19) 0.04212(15) 0.0461(7) Uani 1 1 d . . .
O7 O 0.30490(11) 0.12048(17) 0.00881(11) 0.0279(5) Uani 1 1 d . . .
O8 O 0.36122(11) 0.24498(16) 0.03742(11) 0.0290(5) Uani 1 1 d . . .
C1 C 0.22590(17) 0.6254(2) 0.14216(14) 0.0269(7) Uani 1 1 d . . .
C2 C 0.28275(15) 0.5276(2) 0.21919(14) 0.0216(6) Uani 1 1 d . . .
C3 C 0.25989(14) 0.6016(2) 0.24890(13) 0.0196(6) Uani 1 1 d . . .
C4 C 0.26921(15) 0.6157(2) 0.31064(13) 0.0192(6) Uani 1 1 d . . .
H4 H 0.2919 0.5758 0.3412 0.023 Uiso 1 1 calc R . .
C5 C 0.24303(15) 0.6925(2) 0.32527(13) 0.0195(6) Uani 1 1 d . . .
C6 C 0.20911(18) 0.7516(2) 0.27890(15) 0.0302(8) Uani 1 1 d . . .
H6 H 0.1921 0.8024 0.2896 0.036 Uiso 1 1 calc R . .
C7 C 0.2001(2) 0.7359(3) 0.21684(15) 0.0342(9) Uani 1 1 d . . .
H7 H 0.1774 0.7752 0.1859 0.041 Uiso 1 1 calc R . .
C8 C 0.22632(17) 0.6598(2) 0.20312(14) 0.0246(7) Uani 1 1 d . . .
C9 C 0.25066(15) 0.7118(2) 0.39196(13) 0.0207(6) Uani 1 1 d . . .
C10 C 0.26893(16) 0.4889(2) 0.10947(15) 0.0256(7) Uani 1 1 d . . .
H10A H 0.2300 0.4916 0.0734 0.031 Uiso 1 1 calc R . .
H10B H 0.2730 0.4293 0.1258 0.031 Uiso 1 1 calc R . .
C11 C 0.32552(15) 0.5084(2) 0.08962(13) 0.0208(6) Uani 1 1 d . . .
C12 C 0.36056(17) 0.5862(2) 0.10504(16) 0.0301(8) Uani 1 1 d . . .
H12 H 0.3504 0.6288 0.1291 0.036 Uiso 1 1 calc R . .
C13 C 0.41073(18) 0.5995(3) 0.08411(19) 0.0389(9) Uani 1 1 d . . .
H13 H 0.4344 0.6514 0.0934 0.047 Uiso 1 1 calc R . .
C14 C 0.42522(19) 0.5346(3) 0.0492(2) 0.0429(10) Uani 1 1 d . . .
H14 H 0.4595 0.5415 0.0356 0.052 Uiso 1 1 calc R . .
C15 C 0.38798(17) 0.4588(3) 0.03475(17) 0.0325(8) Uani 1 1 d . . .
H15 H 0.3974 0.4156 0.0106 0.039 Uiso 1 1 calc R . .
C16 C 0.58355(18) -0.0502(3) 0.1058(2) 0.0375(9) Uani 1 1 d . . .
C17 C 0.48690(18) -0.1233(3) 0.06129(17) 0.0328(8) Uani 1 1 d . . .
C18 C 0.47288(16) -0.0271(2) 0.06391(16) 0.0272(7) Uani 1 1 d . . .
C19 C 0.41544(16) 0.0175(2) 0.04405(15) 0.0254(7) Uani 1 1 d . . .
H19 H 0.3769 -0.0122 0.0261 0.030 Uiso 1 1 calc R . .
C20 C 0.41735(15) 0.1095(2) 0.05196(14) 0.0227(6) Uani 1 1 d . . .
C21 C 0.47586(17) 0.1528(2) 0.07813(18) 0.0321(8) Uani 1 1 d . . .
H21 H 0.4764 0.2138 0.0830 0.039 Uiso 1 1 calc R . .
C22 C 0.53323(18) 0.1071(3) 0.0970(2) 0.0403(9) Uani 1 1 d . . .
H22 H 0.5721 0.1364 0.1138 0.048 Uiso 1 1 calc R . .
C23 C 0.53066(16) 0.0166(2) 0.09019(18) 0.0309(8) Uani 1 1 d . . .
C24 C 0.35619(15) 0.1623(2) 0.03113(14) 0.0205(6) Uani 1 1 d . . .
C25 C 0.5873(2) -0.2139(3) 0.0903(2) 0.0432(10) Uani 1 1 d . . .
H25A H 0.6324 -0.2018 0.1002 0.052 Uiso 1 1 calc R . .
H25B H 0.5717 -0.2430 0.0502 0.052 Uiso 1 1 calc R . .
C26 C 0.57937(17) -0.2756(3) 0.13846(18) 0.0334(8) Uani 1 1 d . . .
C27 C 0.5792(2) -0.2432(3) 0.19301(19) 0.0456(10) Uani 1 1 d . . .
H27 H 0.5827 -0.1829 0.2011 0.055 Uiso 1 1 calc R . .
C28 C 0.5737(3) -0.3027(4) 0.2365(2) 0.0630(14) Uani 1 1 d . . .
H28 H 0.5737 -0.2819 0.2745 0.076 Uiso 1 1 calc R . .
C29 C 0.5683(2) -0.3898(4) 0.2248(2) 0.0560(13) Uani 1 1 d . . .
H29 H 0.5645 -0.4294 0.2542 0.067 Uiso 1 1 calc R . .
C30 C 0.5685(2) -0.4189(3) 0.1688(2) 0.0498(11) Uani 1 1 d . . .
H30 H 0.5649 -0.4791 0.1606 0.060 Uiso 1 1 calc R . .
O41 O 0.3030(4) 0.8116(6) 0.0683(4) 0.082(2) Uiso 0.50 1 d PD . .
C41 C 0.2595(4) 0.8818(6) 0.0586(4) 0.050(2) Uiso 0.50 1 d PD . .
H41A H 0.2710 0.9286 0.0357 0.060 Uiso 0.50 1 calc PR . .
H41B H 0.2168 0.8616 0.0343 0.060 Uiso 0.50 1 calc PR . .
C42 C 0.2601(8) 0.9145(12) 0.1157(7) 0.126(6) Uiso 0.50 1 d PD . .
H42A H 0.2202 0.9016 0.1217 0.151 Uiso 0.50 1 calc PR . .
H42B H 0.2672 0.9778 0.1184 0.151 Uiso 0.50 1 calc PR . .
C43 C 0.3152(7) 0.8662(10) 0.1627(6) 0.094(4) Uiso 0.50 1 d PD . .
H43A H 0.3510 0.9059 0.1808 0.113 Uiso 0.50 1 calc PR . .
H43B H 0.3024 0.8424 0.1956 0.113 Uiso 0.50 1 calc PR . .
C44 C 0.3316(5) 0.8009(7) 0.1321(4) 0.060(3) Uiso 0.50 1 d PD . .
H44A H 0.3186 0.7448 0.1442 0.073 Uiso 0.50 1 calc PR . .
H44B H 0.3777 0.8001 0.1433 0.073 Uiso 0.50 1 calc PR . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Zn1 O4 2.034(2) 4_545 ?
Zn1 O3 2.037(2) 6_565 ?
Zn1 N2 2.043(3) . ?
Zn1 O8 2.052(2) . ?
Zn1 O7 2.057(2) 7 ?
Zn1 Zn1 2.9973(7) 7 ?
N1 C1 1.391(4) . ?
N1 C2 1.404(4) . ?
N1 C10 1.451(4) . ?
N2 C15 1.344(4) . ?
N2 C11 1.348(4) . ?
N3 C16 1.391(5) . ?
N3 C17 1.400(5) . ?
N3 C25 1.451(5) . ?
N4 C26 1.358(5) . ?
N4 C30 1.361(6) . ?
O1 C1 1.213(4) . ?
O2 C2 1.210(4) . ?
O3 C9 1.251(4) . ?
O3 Zn1 2.037(2) 6_566 ?
O4 C9 1.250(4) . ?
O4 Zn1 2.034(2) 4 ?
O5 C16 1.208(5) . ?
O6 C17 1.212(5) . ?
O7 C24 1.251(4) . ?
O7 Zn1 2.057(2) 7 ?
O8 C24 1.260(4) . ?
C1 C8 1.495(4) . ?
C2 C3 1.493(4) . ?
C3 C8 1.376(5) . ?
C3 C4 1.380(4) . ?
C4 C5 1.395(4) . ?
C4 H4 0.9300 . ?
C5 C6 1.395(5) . ?
C5 C9 1.513(4) . ?
C6 C7 1.392(4) . ?
C6 H6 0.9300 . ?
C7 C8 1.379(5) . ?
C7 H7 0.9300 . ?
C10 C11 1.518(4) . ?
C10 H10A 0.9700 . ?
C10 H10B 0.9700 . ?
C11 C12 1.390(5) . ?
C12 C13 1.383(5) . ?
C12 H12 0.9300 . ?
C13 C14 1.378(6) . ?
C13 H13 0.9300 . ?
C14 C15 1.387(5) . ?
C14 H14 0.9300 . ?
C15 H15 0.9300 . ?
C16 C23 1.500(5) . ?
C17 C18 1.495(5) . ?
C18 C19 1.379(5) . ?
C18 C23 1.386(5) . ?
C19 C20 1.403(5) . ?
C19 H19 0.9300 . ?
C20 C21 1.396(5) . ?
C20 C24 1.509(4) . ?
C21 C22 1.386(5) . ?
C21 H21 0.9300 . ?
C22 C23 1.378(5) . ?
C22 H22 0.9300 . ?
C25 C26 1.509(5) . ?
C25 H25A 0.9700 . ?
C25 H25B 0.9700 . ?
C26 C27 1.350(6) . ?
C27 C28 1.385(7) . ?
C27 H27 0.9300 . ?
C28 C29 1.343(8) . ?
C28 H28 0.9300 . ?
C29 C30 1.364(7) . ?
C29 H29 0.9300 . ?
C30 H30 0.9300 . ?
O41 C44 1.391(11) . ?
O41 C41 1.405(11) . ?
C41 C42 1.399(15) . ?
C41 H41A 0.9700 . ?
C41 H41B 0.9700 . ?
C42 C43 1.51(2) . ?
C42 H42A 0.9700 . ?
C42 H42B 0.9700 . ?
C43 C44 1.336(14) . ?
C43 H43A 0.9700 . ?
C43 H43B 0.9700 . ?
C44 H44A 0.9700 . ?
C44 H44B 0.9700 . ?

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
O4 Zn1 O3 158.04(10) 4_545 6_565 ?
O4 Zn1 N2 103.92(10) 4_545 . ?
O3 Zn1 N2 97.98(10) 6_565 . ?
O4 Zn1 O8 86.37(10) 4_545 . ?
O3 Zn1 O8 88.45(10) 6_565 . ?
N2 Zn1 O8 99.61(10) . . ?
O4 Zn1 O7 90.50(10) 4_545 7 ?
O3 Zn1 O7 86.50(10) 6_565 7 ?
N2 Zn1 O7 101.94(10) . 7 ?
O8 Zn1 O7 158.34(10) . 7 ?
O4 Zn1 Zn1 74.42(7) 4_545 7 ?
O3 Zn1 Zn1 83.67(7) 6_565 7 ?
N2 Zn1 Zn1 178.35(7) . 7 ?
O8 Zn1 Zn1 80.30(7) . 7 ?
O7 Zn1 Zn1 78.21(7) 7 7 ?
C1 N1 C2 111.9(2) . . ?
C1 N1 C10 123.6(3) . . ?
C2 N1 C10 122.7(3) . . ?
C15 N2 C11 118.6(3) . . ?
C15 N2 Zn1 114.8(2) . . ?
C11 N2 Zn1 126.4(2) . . ?
C16 N3 C17 112.4(3) . . ?
C16 N3 C25 124.1(3) . . ?
C17 N3 C25 123.5(4) . . ?
C26 N4 C30 117.0(4) . . ?
C9 O3 Zn1 121.4(2) . 6_566 ?
C9 O4 Zn1 134.1(2) . 4 ?
C24 O7 Zn1 129.2(2) . 7 ?
C24 O8 Zn1 126.3(2) . . ?
O1 C1 N1 124.8(3) . . ?
O1 C1 C8 129.6(3) . . ?
N1 C1 C8 105.5(3) . . ?
O2 C2 N1 125.1(3) . . ?
O2 C2 C3 129.5(3) . . ?
N1 C2 C3 105.5(3) . . ?
C8 C3 C4 122.3(3) . . ?
C8 C3 C2 108.2(3) . . ?
C4 C3 C2 129.6(3) . . ?
C3 C4 C5 117.0(3) . . ?
C3 C4 H4 121.5 . . ?
C5 C4 H4 121.5 . . ?
C6 C5 C4 120.7(3) . . ?
C6 C5 C9 119.3(3) . . ?
C4 C5 C9 120.0(3) . . ?
C7 C6 C5 121.3(3) . . ?
C7 C6 H6 119.3 . . ?
C5 C6 H6 119.3 . . ?
C8 C7 C6 117.3(3) . . ?
C8 C7 H7 121.3 . . ?
C6 C7 H7 121.3 . . ?
C3 C8 C7 121.4(3) . . ?
C3 C8 C1 108.5(3) . . ?
C7 C8 C1 130.1(3) . . ?
O4 C9 O3 126.0(3) . . ?
O4 C9 C5 116.9(3) . . ?
O3 C9 C5 117.1(3) . . ?
N1 C10 C11 113.2(3) . . ?
N1 C10 H10A 108.9 . . ?
C11 C10 H10A 108.9 . . ?
N1 C10 H10B 108.9 . . ?
C11 C10 H10B 108.9 . . ?
H10A C10 H10B 107.8 . . ?
N2 C11 C12 121.8(3) . . ?
N2 C11 C10 115.4(3) . . ?
C12 C11 C10 122.8(3) . . ?
C13 C12 C11 119.2(3) . . ?
C13 C12 H12 120.4 . . ?
C11 C12 H12 120.4 . . ?
C14 C13 C12 119.1(3) . . ?
C14 C13 H13 120.5 . . ?
C12 C13 H13 120.5 . . ?
C13 C14 C15 119.0(3) . . ?
C13 C14 H14 120.5 . . ?
C15 C14 H14 120.5 . . ?
N2 C15 C14 122.3(3) . . ?
N2 C15 H15 118.9 . . ?
C14 C15 H15 118.9 . . ?
O5 C16 N3 125.8(4) . . ?
O5 C16 C23 128.8(4) . . ?
N3 C16 C23 105.4(3) . . ?
O6 C17 N3 124.5(4) . . ?
O6 C17 C18 129.7(4) . . ?
N3 C17 C18 105.8(3) . . ?
C19 C18 C23 121.7(3) . . ?
C19 C18 C17 130.4(3) . . ?
C23 C18 C17 107.8(3) . . ?
C18 C19 C20 117.5(3) . . ?
C18 C19 H19 121.3 . . ?
C20 C19 H19 121.3 . . ?
C21 C20 C19 120.2(3) . . ?
C21 C20 C24 119.6(3) . . ?
C19 C20 C24 120.2(3) . . ?
C22 C21 C20 121.5(3) . . ?
C22 C21 H21 119.2 . . ?
C20 C21 H21 119.2 . . ?
C23 C22 C21 117.7(3) . . ?
C23 C22 H22 121.2 . . ?
C21 C22 H22 121.2 . . ?
C22 C23 C18 121.3(3) . . ?
C22 C23 C16 130.2(4) . . ?
C18 C23 C16 108.5(3) . . ?
O7 C24 O8 125.6(3) . . ?
O7 C24 C20 117.3(3) . . ?
O8 C24 C20 117.1(3) . . ?
N3 C25 C26 113.2(3) . . ?
N3 C25 H25A 108.9 . . ?
C26 C25 H25A 108.9 . . ?
N3 C25 H25B 108.9 . . ?
C26 C25 H25B 108.9 . . ?
H25A C25 H25B 107.7 . . ?
C27 C26 N4 122.9(4) . . ?
C27 C26 C25 119.9(4) . . ?
N4 C26 C25 117.1(4) . . ?
C26 C27 C28 117.8(4) . . ?
C26 C27 H27 121.1 . . ?
C28 C27 H27 121.1 . . ?
C29 C28 C27 121.3(5) . . ?
C29 C28 H28 119.4 . . ?
C27 C28 H28 119.4 . . ?
C28 C29 C30 118.4(4) . . ?
C28 C29 H29 120.8 . . ?
C30 C29 H29 120.8 . . ?
N4 C30 C29 122.6(5) . . ?
N4 C30 H30 118.7 . . ?
C29 C30 H30 118.7 . . ?
C44 O41 C41 106.8(8) . . ?
C42 C41 O41 110.0(9) . . ?
C42 C41 H41A 109.7 . . ?
O41 C41 H41A 109.7 . . ?
C42 C41 H41B 109.7 . . ?
O41 C41 H41B 109.7 . . ?
H41A C41 H41B 108.2 . . ?
C41 C42 C43 103.7(8) . . ?
C41 C42 H42A 111.0 . . ?
C43 C42 H42A 111.0 . . ?
C41 C42 H42B 111.0 . . ?
C43 C42 H42B 111.0 . . ?
H42A C42 H42B 109.0 . . ?
C44 C43 C42 106.6(8) . . ?
C44 C43 H43A 110.4 . . ?
C42 C43 H43A 110.4 . . ?
C44 C43 H43B 110.4 . . ?
C42 C43 H43B 110.4 . . ?
H43A C43 H43B 108.6 . . ?
C43 C44 O41 111.2(9) . . ?
C43 C44 H44A 109.4 . . ?
O41 C44 H44A 109.4 . . ?
C43 C44 H44B 109.4 . . ?
O41 C44 H44B 109.4 . . ?
H44A C44 H44B 108.0 . . ?

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
O4 Zn1 N2 C15 134.9(2) 4_545 . . . ?
O3 Zn1 N2 C15 -43.5(3) 6_565 . . . ?
O8 Zn1 N2 C15 46.3(3) . . . . ?
O7 Zn1 N2 C15 -131.6(3) 7 . . . ?
Zn1 Zn1 N2 C15 133(3) 7 . . . ?
O4 Zn1 N2 C11 -49.2(3) 4_545 . . . ?
O3 Zn1 N2 C11 132.4(3) 6_565 . . . ?
O8 Zn1 N2 C11 -137.8(3) . . . . ?
O7 Zn1 N2 C11 44.3(3) 7 . . . ?
Zn1 Zn1 N2 C11 -51(3) 7 . . . ?
O4 Zn1 O8 C24 69.0(3) 4_545 . . . ?
O3 Zn1 O8 C24 -89.6(3) 6_565 . . . ?
N2 Zn1 O8 C24 172.5(3) . . . . ?
O7 Zn1 O8 C24 -13.2(4) 7 . . . ?
Zn1 Zn1 O8 C24 -5.8(2) 7 . . . ?
C2 N1 C1 O1 -172.6(4) . . . . ?
C10 N1 C1 O1 -7.4(5) . . . . ?
C2 N1 C1 C8 6.0(4) . . . . ?
C10 N1 C1 C8 171.2(3) . . . . ?
C1 N1 C2 O2 174.5(3) . . . . ?
C10 N1 C2 O2 9.2(5) . . . . ?
C1 N1 C2 C3 -5.8(3) . . . . ?
C10 N1 C2 C3 -171.2(3) . . . . ?
O2 C2 C3 C8 -177.2(3) . . . . ?
N1 C2 C3 C8 3.2(3) . . . . ?
O2 C2 C3 C4 4.0(6) . . . . ?
N1 C2 C3 C4 -175.7(3) . . . . ?
C8 C3 C4 C5 -0.1(5) . . . . ?
C2 C3 C4 C5 178.7(3) . . . . ?
C3 C4 C5 C6 0.0(5) . . . . ?
C3 C4 C5 C9 179.3(3) . . . . ?
C4 C5 C6 C7 0.2(6) . . . . ?
C9 C5 C6 C7 -179.1(3) . . . . ?
C5 C6 C7 C8 -0.2(6) . . . . ?
C4 C3 C8 C7 0.1(5) . . . . ?
C2 C3 C8 C7 -178.9(3) . . . . ?
C4 C3 C8 C1 179.3(3) . . . . ?
C2 C3 C8 C1 0.3(4) . . . . ?
C6 C7 C8 C3 0.1(6) . . . . ?
C6 C7 C8 C1 -179.0(4) . . . . ?
O1 C1 C8 C3 174.7(4) . . . . ?
N1 C1 C8 C3 -3.8(4) . . . . ?
O1 C1 C8 C7 -6.1(7) . . . . ?
N1 C1 C8 C7 175.4(4) . . . . ?
Zn1 O4 C9 O3 -6.0(5) 4 . . . ?
Zn1 O4 C9 C5 174.0(2) 4 . . . ?
Zn1 O3 C9 O4 7.8(5) 6_566 . . . ?
Zn1 O3 C9 C5 -172.3(2) 6_566 . . . ?
C6 C5 C9 O4 1.3(5) . . . . ?
C4 C5 C9 O4 -178.0(3) . . . . ?
C6 C5 C9 O3 -178.6(3) . . . . ?
C4 C5 C9 O3 2.1(4) . . . . ?
C1 N1 C10 C11 94.1(4) . . . . ?
C2 N1 C10 C11 -102.3(4) . . . . ?
C15 N2 C11 C12 1.1(5) . . . . ?
Zn1 N2 C11 C12 -174.6(2) . . . . ?
C15 N2 C11 C10 179.5(3) . . . . ?
Zn1 N2 C11 C10 3.8(4) . . . . ?
N1 C10 C11 N2 169.5(3) . . . . ?
N1 C10 C11 C12 -12.1(5) . . . . ?
N2 C11 C12 C13 -0.5(5) . . . . ?
C10 C11 C12 C13 -178.8(3) . . . . ?
C11 C12 C13 C14 -0.9(6) . . . . ?
C12 C13 C14 C15 1.7(7) . . . . ?
C11 N2 C15 C14 -0.3(5) . . . . ?
Zn1 N2 C15 C14 175.9(3) . . . . ?
C13 C14 C15 N2 -1.1(7) . . . . ?
C17 N3 C16 O5 178.2(4) . . . . ?
C25 N3 C16 O5 -1.7(6) . . . . ?
C17 N3 C16 C23 -2.1(4) . . . . ?
C25 N3 C16 C23 178.0(3) . . . . ?
C16 N3 C17 O6 -178.6(4) . . . . ?
C25 N3 C17 O6 1.3(6) . . . . ?
C16 N3 C17 C18 1.9(4) . . . . ?
C25 N3 C17 C18 -178.3(3) . . . . ?
O6 C17 C18 C19 -1.8(7) . . . . ?
N3 C17 C18 C19 177.8(3) . . . . ?
O6 C17 C18 C23 179.7(4) . . . . ?
N3 C17 C18 C23 -0.8(4) . . . . ?
C23 C18 C19 C20 -0.6(5) . . . . ?
C17 C18 C19 C20 -179.0(3) . . . . ?
C18 C19 C20 C21 1.1(5) . . . . ?
C18 C19 C20 C24 179.9(3) . . . . ?
C19 C20 C21 C22 -0.2(6) . . . . ?
C24 C20 C21 C22 -179.0(3) . . . . ?
C20 C21 C22 C23 -1.2(6) . . . . ?
C21 C22 C23 C18 1.6(6) . . . . ?
C21 C22 C23 C16 179.7(4) . . . . ?
C19 C18 C23 C22 -0.7(6) . . . . ?
C17 C18 C23 C22 178.0(4) . . . . ?
C19 C18 C23 C16 -179.2(3) . . . . ?
C17 C18 C23 C16 -0.5(4) . . . . ?
O5 C16 C23 C22 2.9(8) . . . . ?
N3 C16 C23 C22 -176.8(4) . . . . ?
O5 C16 C23 C18 -178.8(4) . . . . ?
N3 C16 C23 C18 1.6(4) . . . . ?
Zn1 O7 C24 O8 -2.6(5) 7 . . . ?
Zn1 O7 C24 C20 177.8(2) 7 . . . ?
Zn1 O8 C24 O7 7.0(5) . . . . ?
Zn1 O8 C24 C20 -173.35(19) . . . . ?
C21 C20 C24 O7 -179.0(3) . . . . ?
C19 C20 C24 O7 2.2(4) . . . . ?
C21 C20 C24 O8 1.4(4) . . . . ?
C19 C20 C24 O8 -177.5(3) . . . . ?
C16 N3 C25 C26 109.1(4) . . . . ?
C17 N3 C25 C26 -70.8(5) . . . . ?
C30 N4 C26 C27 -0.8(6) . . . . ?
C30 N4 C26 C25 178.1(3) . . . . ?
N3 C25 C26 C27 -38.9(6) . . . . ?
N3 C25 C26 N4 142.2(4) . . . . ?
N4 C26 C27 C28 0.7(7) . . . . ?
C25 C26 C27 C28 -178.2(4) . . . . ?
C26 C27 C28 C29 -0.3(8) . . . . ?
C27 C28 C29 C30 0.1(8) . . . . ?
C26 N4 C30 C29 0.5(6) . . . . ?
C28 C29 C30 N4 -0.2(7) . . . . ?
C44 O41 C41 C42 -0.7(14) . . . . ?
O41 C41 C42 C43 7.7(17) . . . . ?
C41 C42 C43 C44 -12.3(18) . . . . ?
C42 C43 C44 O41 12.6(17) . . . . ?
C41 O41 C44 C43 -7.9(14) . . . . ?

_diffrn_measured_fraction_theta_max 0.846
_diffrn_reflns_theta_full        26.00
_diffrn_measured_fraction_theta_full 0.999
_refine_diff_density_max         1.692
_refine_diff_density_min         -0.399
_refine_diff_density_rms         0.112

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
1 0.500 0.226 0.250 393.7 21.7
2 0.500 -0.226 0.750 393.7 21.9
3 0.000 0.274 0.750 393.7 21.9
4 0.000 0.726 0.250 393.7 21.7
_platon_squeeze_details          
;
;

_database_code_depnum_ccdc_archive 'CCDC 973185'
#######################################################################
#
#                 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_cpd_2

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
 ?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C60 H38 Cl2 N8 O16 Zn2'
_chemical_formula_weight         1328.62

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'
Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_symmetry_cell_setting           Triclinic
_symmetry_space_group_name_H-M   P-1

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

_cell_length_a                   9.1510(3)
_cell_length_b                   12.4798(4)
_cell_length_c                   12.9559(3)
_cell_angle_alpha                107.884(2)
_cell_angle_beta                 90.393(2)
_cell_angle_gamma                95.349(2)
_cell_volume                     1400.99(7)
_cell_formula_units_Z            1
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    0
_cell_measurement_theta_min      0
_cell_measurement_theta_max      0

_exptl_crystal_description       prism
_exptl_crystal_colour            colorless
_exptl_crystal_size_max          0.40
_exptl_crystal_size_mid          0.32
_exptl_crystal_size_min          0.05
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.575
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             676
_exptl_absorpt_coefficient_mu    1.033
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.6828
_exptl_absorpt_correction_T_max  0.9502
_exptl_absorpt_process_details   ?

_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      296(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  KappaCCD
_diffrn_measurement_method       'CCD rotation images, thick slices'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            9845
_diffrn_reflns_av_R_equivalents  0.0323
_diffrn_reflns_av_sigmaI/netI    0.0583
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_theta_min         1.72
_diffrn_reflns_theta_max         25.16
_reflns_number_total             4957
_reflns_number_gt                3639
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'Collect (Nonius BV, 1997-2000)'
_computing_cell_refinement       'HKL Scalepack (Otwinowski & Minor 1997)'
_computing_data_reduction        
'HKL Denzo and Scalepack (Otwinowski&Minor 1997)'
_computing_structure_solution    'SHELXS-86 (Sheldrick, 1986)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    ?
_computing_publication_material  ?

_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)+(0.0629P)²+0.4845P] 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         4957
_refine_ls_number_parameters     398
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0673
_refine_ls_R_factor_gt           0.0426
_refine_ls_wR_factor_ref         0.1332
_refine_ls_wR_factor_gt          0.1003
_refine_ls_goodness_of_fit_ref   1.074
_refine_ls_restrained_S_all      1.074
_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 0.75328(5) 0.79455(4) 0.55532(3) 0.03783(17) Uani 1 1 d . . .
Cl1 Cl 0.59953(12) 0.80764(9) 0.42695(8) 0.0488(3) Uani 1 1 d . . .
O1 O 1.4008(4) 0.7655(3) 0.7486(2) 0.0649(9) Uani 1 1 d . . .
O2 O 1.1952(4) 1.0950(3) 0.7915(2) 0.0647(10) Uani 1 1 d . . .
O3 O 1.1278(3) 1.1781(3) 1.2361(2) 0.0514(8) Uani 1 1 d . . .
O4 O 1.2874(3) 1.0950(2) 1.3052(2) 0.0437(7) Uani 1 1 d . . .
O5 O 0.5858(4) 0.6695(3) 0.9327(3) 0.0791(12) Uani 1 1 d . . .
O6 O 0.6905(5) 0.3063(3) 0.7830(3) 0.0800(12) Uani 1 1 d . . .
O7 O 1.0057(5) 0.2956(3) 1.1313(3) 0.0783(12) Uani 1 1 d . . .
H7 H 1.0398 0.2651 1.1726 0.117 Uiso 1 1 calc R . .
O8 O 0.9999(5) 0.4386(3) 1.2822(3) 0.0889(13) Uani 1 1 d . . .
N1 N 1.3049(4) 0.9283(3) 0.7433(2) 0.0400(8) Uani 1 1 d . . .
N2 N 0.9578(4) 0.8313(3) 0.5080(2) 0.0366(8) Uani 1 1 d . . .
N3 N 0.6202(4) 0.4875(3) 0.8335(3) 0.0448(9) Uani 1 1 d . . .
N4 N 0.7300(4) 0.6326(3) 0.5609(3) 0.0408(8) Uani 1 1 d . . .
C1 C 1.3511(5) 0.8529(4) 0.7942(3) 0.0420(10) Uani 1 1 d . . .
C2 C 1.2441(5) 1.0189(4) 0.8152(3) 0.0421(10) Uani 1 1 d . . .
C3 C 1.2560(4) 1.0013(3) 0.9242(3) 0.0369(9) Uani 1 1 d . . .
C4 C 1.2181(5) 1.0686(3) 1.0240(3) 0.0416(10) Uani 1 1 d . . .
H4 H 1.1703 1.1329 1.0311 0.050 Uiso 1 1 calc R . .
C5 C 1.2544(4) 1.0364(3) 1.1141(3) 0.0362(9) Uani 1 1 d . . .
C6 C 1.3241(5) 0.9384(3) 1.1018(3) 0.0423(10) Uani 1 1 d . . .
H6 H 1.3479 0.9188 1.1630 0.051 Uiso 1 1 calc R . .
C7 C 1.3587(5) 0.8695(3) 0.9999(3) 0.0445(10) Uani 1 1 d . . .
H7A H 1.4034 0.8035 0.9916 0.053 Uiso 1 1 calc R . .
C8 C 1.3234(4) 0.9037(3) 0.9122(3) 0.0361(9) Uani 1 1 d . . .
C9 C 1.2179(5) 1.1091(3) 1.2260(3) 0.0387(10) Uani 1 1 d . . .
C10 C 1.3404(5) 0.9233(4) 0.6318(3) 0.0461(11) Uani 1 1 d . . .
H10A H 1.4117 0.8690 0.6066 0.055 Uiso 1 1 calc R . .
H10B H 1.3865 0.9967 0.6326 0.055 Uiso 1 1 calc R . .
C11 C 1.0750(4) 0.8552(3) 0.5766(3) 0.0374(9) Uani 1 1 d . . .
H11 H 1.0623 0.8466 0.6449 0.045 Uiso 1 1 calc R . .
C12 C 1.2118(4) 0.8912(3) 0.5522(3) 0.0354(9) Uani 1 1 d . . .
C13 C 1.2294(5) 0.9015(3) 0.4492(3) 0.0411(10) Uani 1 1 d . . .
H13 H 1.3209 0.9258 0.4291 0.049 Uiso 1 1 calc R . .
C14 C 1.1117(5) 0.8757(4) 0.3774(3) 0.0451(11) Uani 1 1 d . . .
H14 H 1.1229 0.8806 0.3077 0.054 Uiso 1 1 calc R . .
C15 C 0.9777(5) 0.8428(3) 0.4092(3) 0.0414(10) Uani 1 1 d . . .
H15 H 0.8973 0.8278 0.3608 0.050 Uiso 1 1 calc R . .
C16 C 0.6370(5) 0.5819(4) 0.9246(3) 0.0490(11) Uani 1 1 d . . .
C17 C 0.6912(5) 0.3980(4) 0.8484(4) 0.0512(12) Uani 1 1 d . . .
C18 C 0.7599(5) 0.4421(3) 0.9588(3) 0.0430(10) Uani 1 1 d . . .
C19 C 0.8412(5) 0.3893(4) 1.0150(3) 0.0454(11) Uani 1 1 d . . .
H19 H 0.8638 0.3154 0.9834 0.054 Uiso 1 1 calc R . .
C20 C 0.8880(5) 0.4497(4) 1.1198(3) 0.0438(10) Uani 1 1 d . . .
C21 C 0.8568(6) 0.5602(4) 1.1659(4) 0.0581(13) Uani 1 1 d . . .
H21 H 0.8907 0.5995 1.2364 0.070 Uiso 1 1 calc R . .
C22 C 0.7764(6) 0.6133(4) 1.1093(4) 0.0614(14) Uani 1 1 d . . .
H22 H 0.7558 0.6878 1.1402 0.074 Uiso 1 1 calc R . .
C23 C 0.7279(5) 0.5522(3) 1.0054(3) 0.0454(11) Uani 1 1 d . . .
C24 C 0.9710(5) 0.3962(4) 1.1873(4) 0.0522(12) Uani 1 1 d . . .
C25 C 0.5329(5) 0.4798(4) 0.7362(3) 0.0483(11) Uani 1 1 d . . .
H25A H 0.4620 0.5352 0.7550 0.058 Uiso 1 1 calc R . .
H25B H 0.4789 0.4054 0.7101 0.058 Uiso 1 1 calc R . .
C26 C 0.6489(5) 0.6070(4) 0.6374(3) 0.0427(10) Uani 1 1 d . . .
H26 H 0.6062 0.6650 0.6875 0.051 Uiso 1 1 calc R . .
C27 C 0.6254(5) 0.4997(3) 0.6460(3) 0.0409(10) Uani 1 1 d . . .
C28 C 0.6898(6) 0.4144(4) 0.5711(4) 0.0559(12) Uani 1 1 d . . .
H28 H 0.6769 0.3406 0.5741 0.067 Uiso 1 1 calc R . .
C29 C 0.7730(6) 0.4396(4) 0.4923(4) 0.0608(13) Uani 1 1 d . . .
H29 H 0.8161 0.3829 0.4411 0.073 Uiso 1 1 calc R . .
C30 C 0.7924(5) 0.5492(4) 0.4896(3) 0.0491(11) Uani 1 1 d . . .
H30 H 0.8504 0.5658 0.4368 0.059 Uiso 1 1 calc R . .


_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 O4 1.969(3) 2_777 ?
Zn1 N2 2.029(3) . ?
Zn1 N4 2.036(3) . ?
Zn1 Cl1 2.2248(11) . ?
O1 C1 1.202(5) . ?
O2 C2 1.205(5) . ?
O3 C9 1.227(5) . ?
O4 C9 1.269(4) . ?
O4 Zn1 1.969(3) 2_777 ?
O5 C16 1.205(5) . ?
O6 C17 1.196(5) . ?
O7 C24 1.313(5) . ?
O7 H7 0.8200 . ?
O8 C24 1.196(5) . ?
N1 C2 1.391(5) . ?
N1 C1 1.396(5) . ?
N1 C10 1.466(5) . ?
N2 C11 1.339(5) . ?
N2 C15 1.343(5) . ?
N3 C16 1.384(5) . ?
N3 C17 1.405(5) . ?
N3 C25 1.460(5) . ?
N4 C30 1.338(5) . ?
N4 C26 1.341(5) . ?
C1 C8 1.498(5) . ?
C2 C3 1.499(5) . ?
C3 C4 1.375(5) . ?
C3 C8 1.384(5) . ?
C4 C5 1.394(5) . ?
C4 H4 0.9300 . ?
C5 C6 1.397(5) . ?
C5 C9 1.515(5) . ?
C6 C7 1.393(5) . ?
C6 H6 0.9300 . ?
C7 C8 1.377(5) . ?
C7 H7A 0.9300 . ?
C10 C12 1.501(5) . ?
C10 H10A 0.9700 . ?
C10 H10B 0.9700 . ?
C11 C12 1.363(5) . ?
C11 H11 0.9300 . ?
C12 C13 1.388(5) . ?
C13 C14 1.366(6) . ?
C13 H13 0.9300 . ?
C14 C15 1.364(6) . ?
C14 H14 0.9300 . ?
C15 H15 0.9300 . ?
C16 C23 1.486(6) . ?
C17 C18 1.478(6) . ?
C18 C19 1.377(5) . ?
C18 C23 1.381(5) . ?
C19 C20 1.377(5) . ?
C19 H19 0.9300 . ?
C20 C21 1.382(6) . ?
C20 C24 1.494(6) . ?
C21 C22 1.379(6) . ?
C21 H21 0.9300 . ?
C22 C23 1.374(6) . ?
C22 H22 0.9300 . ?
C25 C27 1.516(6) . ?
C25 H25A 0.9700 . ?
C25 H25B 0.9700 . ?
C26 C27 1.375(5) . ?
C26 H26 0.9300 . ?
C27 C28 1.383(6) . ?
C28 C29 1.372(6) . ?
C28 H28 0.9300 . ?
C29 C30 1.374(6) . ?
C29 H29 0.9300 . ?
C30 H30 0.9300 . ?

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
O4 Zn1 N2 110.74(12) 2_777 . ?
O4 Zn1 N4 112.38(12) 2_777 . ?
N2 Zn1 N4 109.83(13) . . ?
O4 Zn1 Cl1 109.22(8) 2_777 . ?
N2 Zn1 Cl1 105.77(9) . . ?
N4 Zn1 Cl1 108.66(10) . . ?
C9 O4 Zn1 112.2(2) . 2_777 ?
C24 O7 H7 109.5 . . ?
C2 N1 C1 112.4(3) . . ?
C2 N1 C10 123.4(3) . . ?
C1 N1 C10 123.4(3) . . ?
C11 N2 C15 117.6(4) . . ?
C11 N2 Zn1 121.6(3) . . ?
C15 N2 Zn1 120.5(3) . . ?
C16 N3 C17 111.5(3) . . ?
C16 N3 C25 124.2(3) . . ?
C17 N3 C25 124.2(3) . . ?
C30 N4 C26 118.1(4) . . ?
C30 N4 Zn1 122.2(3) . . ?
C26 N4 Zn1 119.7(3) . . ?
O1 C1 N1 124.9(4) . . ?
O1 C1 C8 129.3(4) . . ?
N1 C1 C8 105.8(3) . . ?
O2 C2 N1 125.4(4) . . ?
O2 C2 C3 129.0(4) . . ?
N1 C2 C3 105.6(3) . . ?
C4 C3 C8 122.0(3) . . ?
C4 C3 C2 129.6(4) . . ?
C8 C3 C2 108.3(3) . . ?
C3 C4 C5 117.2(4) . . ?
C3 C4 H4 121.4 . . ?
C5 C4 H4 121.4 . . ?
C4 C5 C6 120.6(3) . . ?
C4 C5 C9 119.2(3) . . ?
C6 C5 C9 120.2(3) . . ?
C7 C6 C5 121.6(4) . . ?
C7 C6 H6 119.2 . . ?
C5 C6 H6 119.2 . . ?
C8 C7 C6 116.7(4) . . ?
C8 C7 H7A 121.6 . . ?
C6 C7 H7A 121.6 . . ?
C7 C8 C3 121.8(3) . . ?
C7 C8 C1 130.3(4) . . ?
C3 C8 C1 107.9(3) . . ?
O3 C9 O4 123.8(4) . . ?
O3 C9 C5 120.1(3) . . ?
O4 C9 C5 116.1(4) . . ?
N1 C10 C12 115.0(3) . . ?
N1 C10 H10A 108.5 . . ?
C12 C10 H10A 108.5 . . ?
N1 C10 H10B 108.5 . . ?
C12 C10 H10B 108.5 . . ?
H10A C10 H10B 107.5 . . ?
N2 C11 C12 123.8(4) . . ?
N2 C11 H11 118.1 . . ?
C12 C11 H11 118.1 . . ?
C11 C12 C13 117.3(4) . . ?
C11 C12 C10 123.2(3) . . ?
C13 C12 C10 119.4(4) . . ?
C14 C13 C12 119.7(4) . . ?
C14 C13 H13 120.1 . . ?
C12 C13 H13 120.1 . . ?
C15 C14 C13 119.3(4) . . ?
C15 C14 H14 120.4 . . ?
C13 C14 H14 120.4 . . ?
N2 C15 C14 122.2(4) . . ?
N2 C15 H15 118.9 . . ?
C14 C15 H15 118.9 . . ?
O5 C16 N3 124.5(4) . . ?
O5 C16 C23 128.8(4) . . ?
N3 C16 C23 106.7(3) . . ?
O6 C17 N3 124.8(4) . . ?
O6 C17 C18 129.7(4) . . ?
N3 C17 C18 105.5(4) . . ?
C19 C18 C23 121.2(4) . . ?
C19 C18 C17 129.8(4) . . ?
C23 C18 C17 109.0(4) . . ?
C18 C19 C20 117.7(4) . . ?
C18 C19 H19 121.2 . . ?
C20 C19 H19 121.2 . . ?
C19 C20 C21 121.0(4) . . ?
C19 C20 C24 120.6(4) . . ?
C21 C20 C24 118.3(4) . . ?
C22 C21 C20 121.3(4) . . ?
C22 C21 H21 119.4 . . ?
C20 C21 H21 119.4 . . ?
C23 C22 C21 117.5(4) . . ?
C23 C22 H22 121.2 . . ?
C21 C22 H22 121.2 . . ?
C22 C23 C18 121.3(4) . . ?
C22 C23 C16 131.3(4) . . ?
C18 C23 C16 107.4(4) . . ?
O8 C24 O7 123.5(4) . . ?
O8 C24 C20 124.2(4) . . ?
O7 C24 C20 112.3(4) . . ?
N3 C25 C27 112.9(4) . . ?
N3 C25 H25A 109.0 . . ?
C27 C25 H25A 109.0 . . ?
N3 C25 H25B 109.0 . . ?
C27 C25 H25B 109.0 . . ?
H25A C25 H25B 107.8 . . ?
N4 C26 C27 123.6(4) . . ?
N4 C26 H26 118.2 . . ?
C27 C26 H26 118.2 . . ?
C26 C27 C28 117.6(4) . . ?
C26 C27 C25 119.4(4) . . ?
C28 C27 C25 123.0(4) . . ?
C29 C28 C27 119.4(4) . . ?
C29 C28 H28 120.3 . . ?
C27 C28 H28 120.3 . . ?
C28 C29 C30 119.7(4) . . ?
C28 C29 H29 120.2 . . ?
C30 C29 H29 120.2 . . ?
N4 C30 C29 121.8(4) . . ?
N4 C30 H30 119.1 . . ?
C29 C30 H30 119.1 . . ?

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
O4 Zn1 N2 C11 47.2(3) 2_777 . . . ?
N4 Zn1 N2 C11 -77.5(3) . . . . ?
Cl1 Zn1 N2 C11 165.4(3) . . . . ?
O4 Zn1 N2 C15 -126.5(3) 2_777 . . . ?
N4 Zn1 N2 C15 108.7(3) . . . . ?
Cl1 Zn1 N2 C15 -8.3(3) . . . . ?
O4 Zn1 N4 C30 -159.6(3) 2_777 . . . ?
N2 Zn1 N4 C30 -35.8(4) . . . . ?
Cl1 Zn1 N4 C30 79.4(3) . . . . ?
O4 Zn1 N4 C26 21.0(3) 2_777 . . . ?
N2 Zn1 N4 C26 144.7(3) . . . . ?
Cl1 Zn1 N4 C26 -100.0(3) . . . . ?
C2 N1 C1 O1 176.3(4) . . . . ?
C10 N1 C1 O1 -14.0(7) . . . . ?
C2 N1 C1 C8 -2.9(5) . . . . ?
C10 N1 C1 C8 166.7(4) . . . . ?
C1 N1 C2 O2 -179.5(5) . . . . ?
C10 N1 C2 O2 10.8(7) . . . . ?
C1 N1 C2 C3 1.5(5) . . . . ?
C10 N1 C2 C3 -168.1(4) . . . . ?
O2 C2 C3 C4 -1.9(8) . . . . ?
N1 C2 C3 C4 177.0(4) . . . . ?
O2 C2 C3 C8 -178.3(5) . . . . ?
N1 C2 C3 C8 0.6(5) . . . . ?
C8 C3 C4 C5 1.9(6) . . . . ?
C2 C3 C4 C5 -174.1(4) . . . . ?
C3 C4 C5 C6 -1.1(6) . . . . ?
C3 C4 C5 C9 178.7(4) . . . . ?
C4 C5 C6 C7 -0.4(7) . . . . ?
C9 C5 C6 C7 179.7(4) . . . . ?
C5 C6 C7 C8 1.2(6) . . . . ?
C6 C7 C8 C3 -0.4(6) . . . . ?
C6 C7 C8 C1 176.9(4) . . . . ?
C4 C3 C8 C7 -1.2(7) . . . . ?
C2 C3 C8 C7 175.6(4) . . . . ?
C4 C3 C8 C1 -179.1(4) . . . . ?
C2 C3 C8 C1 -2.3(5) . . . . ?
O1 C1 C8 C7 6.4(8) . . . . ?
N1 C1 C8 C7 -174.5(4) . . . . ?
O1 C1 C8 C3 -176.0(5) . . . . ?
N1 C1 C8 C3 3.2(5) . . . . ?
Zn1 O4 C9 O3 -4.9(5) 2_777 . . . ?
Zn1 O4 C9 C5 173.7(3) 2_777 . . . ?
C4 C5 C9 O3 17.6(6) . . . . ?
C6 C5 C9 O3 -162.6(4) . . . . ?
C4 C5 C9 O4 -161.1(4) . . . . ?
C6 C5 C9 O4 18.8(6) . . . . ?
C2 N1 C10 C12 -78.8(5) . . . . ?
C1 N1 C10 C12 112.7(4) . . . . ?
C15 N2 C11 C12 0.7(6) . . . . ?
Zn1 N2 C11 C12 -173.2(3) . . . . ?
N2 C11 C12 C13 -1.2(6) . . . . ?
N2 C11 C12 C10 176.8(4) . . . . ?
N1 C10 C12 C11 -8.1(6) . . . . ?
N1 C10 C12 C13 169.8(4) . . . . ?
C11 C12 C13 C14 0.0(6) . . . . ?
C10 C12 C13 C14 -178.0(4) . . . . ?
C12 C13 C14 C15 1.5(6) . . . . ?
C11 N2 C15 C14 1.0(6) . . . . ?
Zn1 N2 C15 C14 175.0(3) . . . . ?
C13 C14 C15 N2 -2.1(6) . . . . ?
C17 N3 C16 O5 -179.5(5) . . . . ?
C25 N3 C16 O5 -2.6(7) . . . . ?
C17 N3 C16 C23 0.7(5) . . . . ?
C25 N3 C16 C23 177.6(4) . . . . ?
C16 N3 C17 O6 178.2(5) . . . . ?
C25 N3 C17 O6 1.3(8) . . . . ?
C16 N3 C17 C18 -0.8(5) . . . . ?
C25 N3 C17 C18 -177.7(4) . . . . ?
O6 C17 C18 C19 0.2(9) . . . . ?
N3 C17 C18 C19 179.1(4) . . . . ?
O6 C17 C18 C23 -178.4(5) . . . . ?
N3 C17 C18 C23 0.6(5) . . . . ?
C23 C18 C19 C20 0.8(7) . . . . ?
C17 C18 C19 C20 -177.6(4) . . . . ?
C18 C19 C20 C21 -1.3(7) . . . . ?
C18 C19 C20 C24 177.3(4) . . . . ?
C19 C20 C21 C22 0.8(8) . . . . ?
C24 C20 C21 C22 -177.8(5) . . . . ?
C20 C21 C22 C23 0.2(8) . . . . ?
C21 C22 C23 C18 -0.7(7) . . . . ?
C21 C22 C23 C16 178.1(5) . . . . ?
C19 C18 C23 C22 0.2(7) . . . . ?
C17 C18 C23 C22 178.9(4) . . . . ?
C19 C18 C23 C16 -178.8(4) . . . . ?
C17 C18 C23 C16 -0.2(5) . . . . ?
O5 C16 C23 C22 0.9(9) . . . . ?
N3 C16 C23 C22 -179.3(5) . . . . ?
O5 C16 C23 C18 179.9(5) . . . . ?
N3 C16 C23 C18 -0.3(5) . . . . ?
C19 C20 C24 O8 -170.8(5) . . . . ?
C21 C20 C24 O8 7.8(8) . . . . ?
C19 C20 C24 O7 7.5(6) . . . . ?
C21 C20 C24 O7 -173.9(4) . . . . ?
C16 N3 C25 C27 99.6(5) . . . . ?
C17 N3 C25 C27 -83.8(5) . . . . ?
C30 N4 C26 C27 -0.6(6) . . . . ?
Zn1 N4 C26 C27 178.9(3) . . . . ?
N4 C26 C27 C28 0.1(6) . . . . ?
N4 C26 C27 C25 179.5(4) . . . . ?
N3 C25 C27 C26 -92.6(5) . . . . ?
N3 C25 C27 C28 86.7(5) . . . . ?
C26 C27 C28 C29 -0.1(7) . . . . ?
C25 C27 C28 C29 -179.5(4) . . . . ?
C27 C28 C29 C30 0.6(7) . . . . ?
C26 N4 C30 C29 1.1(6) . . . . ?
Zn1 N4 C30 C29 -178.3(3) . . . . ?
C28 C29 C30 N4 -1.2(8) . . . . ?

_diffrn_measured_fraction_theta_max 0.991
_diffrn_reflns_theta_full        25.16
_diffrn_measured_fraction_theta_full 0.991
_refine_diff_density_max         0.329
_refine_diff_density_min         -0.360
_refine_diff_density_rms         0.092
_database_code_depnum_ccdc_archive 'CCDC 973186'
#######################################################################
#
#                 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_cpd_3

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
 ?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C30 H19 N4 O8.50 Zn'
_chemical_formula_weight         636.86

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   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                   19.2567(15)
_cell_length_b                   18.6939(15)
_cell_length_c                   7.9020(6)
_cell_angle_alpha                90.00
_cell_angle_beta                 98.917(3)
_cell_angle_gamma                90.00
_cell_volume                     2810.2(4)
_cell_formula_units_Z            4
_cell_measurement_temperature    150(2)
_cell_measurement_reflns_used    8649
_cell_measurement_theta_min      2.88
_cell_measurement_theta_max      26.39

_exptl_crystal_description       needle
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.25
_exptl_crystal_size_mid          0.12
_exptl_crystal_size_min          0.10
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.505
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1300
_exptl_absorpt_coefficient_mu    0.935
_exptl_absorpt_correction_type   none
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   ?

_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      150(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            15703
_diffrn_reflns_av_R_equivalents  0.0262
_diffrn_reflns_av_sigmaI/netI    0.0191
_diffrn_reflns_limit_h_min       -24
_diffrn_reflns_limit_h_max       24
_diffrn_reflns_limit_k_min       -23
_diffrn_reflns_limit_k_max       23
_diffrn_reflns_limit_l_min       -8
_diffrn_reflns_limit_l_max       9
_diffrn_reflns_theta_min         2.14
_diffrn_reflns_theta_max         26.43
_reflns_number_total             2885
_reflns_number_gt                2610
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.35.19 (release 27-10-2011 CrysAlis171 .NET)
(compiled Oct 27 2011,15:02:11)
;
_computing_cell_refinement       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.35.19 (release 27-10-2011 CrysAlis171 .NET)
(compiled Oct 27 2011,15:02:11)
;
_computing_data_reduction        
;
CrysAlisPro, Agilent Technologies,
Version 1.171.35.19 (release 27-10-2011 CrysAlis171 .NET)
(compiled Oct 27 2011,15:02:11)
;
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    ?
_computing_publication_material  ?

_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)+(0.0462P)²+13.6129P] 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         2885
_refine_ls_number_parameters     199
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0523
_refine_ls_R_factor_gt           0.0460
_refine_ls_wR_factor_ref         0.1369
_refine_ls_wR_factor_gt          0.1316
_refine_ls_goodness_of_fit_ref   1.186
_refine_ls_restrained_S_all      1.186
_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 0.0000 -0.19073(3) 0.2500 0.02589(18) Uani 1 2 d S . .
O1 O 0.40760(15) 0.00229(18) 0.8649(4) 0.0511(8) Uani 1 1 d . . .
O2 O 0.21997(15) 0.11966(14) 0.5689(4) 0.0417(6) Uani 1 1 d . . .
O3 O 0.07437(12) -0.12676(13) 0.3572(3) 0.0346(6) Uani 1 1 d . . .
O4 O 0.12864(13) -0.22817(13) 0.4421(3) 0.0348(6) Uani 1 1 d . . .
N1 N 0.32155(16) 0.07616(17) 0.7271(4) 0.0328(7) Uani 1 1 d . . .
N2 N 0.45915(14) 0.25280(16) 0.4273(3) 0.0266(6) Uani 1 1 d . . .
C1 C 0.35150(19) 0.0104(2) 0.7745(4) 0.0355(8) Uani 1 1 d . . .
C2 C 0.25582(18) 0.0698(2) 0.6249(4) 0.0318(8) Uani 1 1 d . . .
C3 C 0.24286(17) -0.00822(19) 0.6045(4) 0.0267(7) Uani 1 1 d . . .
C4 C 0.18549(17) -0.04446(19) 0.5188(4) 0.0278(7) Uani 1 1 d . . .
H4 H 0.1471 -0.0200 0.4599 0.033 Uiso 1 1 calc R . .
C5 C 0.18727(16) -0.11899(19) 0.5236(4) 0.0252(7) Uani 1 1 d . . .
C6 C 0.24570(17) -0.1546(2) 0.6109(4) 0.0285(7) Uani 1 1 d . . .
H6 H 0.2463 -0.2043 0.6114 0.034 Uiso 1 1 calc R . .
C7 C 0.30311(17) -0.1176(2) 0.6973(4) 0.0314(8) Uani 1 1 d . . .
H7 H 0.3419 -0.1416 0.7557 0.038 Uiso 1 1 calc R . .
C8 C 0.30041(17) -0.0443(2) 0.6930(4) 0.0285(7) Uani 1 1 d . . .
C9 C 0.12622(17) -0.16287(19) 0.4351(4) 0.0282(7) Uani 1 1 d . . .
C10 C 0.3514(2) 0.1447(2) 0.7871(5) 0.0409(9) Uani 1 1 d . . .
H10A H 0.3841 0.1373 0.8921 0.049 Uiso 1 1 calc R . .
H10B H 0.3141 0.1756 0.8136 0.049 Uiso 1 1 calc R . .
C11 C 0.4103(2) 0.2859(2) 0.5014(6) 0.0434(10) Uani 1 1 d . . .
H11 H 0.3997 0.3335 0.4739 0.052 Uiso 1 1 calc R . .
C12 C 0.3750(2) 0.2517(2) 0.6178(5) 0.0432(10) Uani 1 1 d . . .
H12 H 0.3418 0.2765 0.6686 0.052 Uiso 1 1 calc R . .
C13 C 0.38913(18) 0.1815(2) 0.6584(4) 0.0307(8) Uani 1 1 d . . .
C14 C 0.43951(19) 0.1470(2) 0.5807(4) 0.0320(8) Uani 1 1 d . . .
H14 H 0.4505 0.0993 0.6046 0.038 Uiso 1 1 calc R . .
C15 C 0.47304(17) 0.18489(19) 0.4670(4) 0.0281(7) Uani 1 1 d . . .
H15 H 0.5071 0.1616 0.4157 0.034 Uiso 1 1 calc R . .
O5 O 0.0146(11) 0.0352(11) 0.426(3) 0.095(6) Uiso 0.25 1 d P . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Zn1 O3 1.955(2) . ?
Zn1 O3 1.955(2) 2 ?
Zn1 N2 2.010(3) 4_545 ?
Zn1 N2 2.010(3) 3_445 ?
O1 C1 1.209(5) . ?
O2 C2 1.202(5) . ?
O3 C9 1.281(4) . ?
O4 C9 1.222(4) . ?
N1 C1 1.385(5) . ?
N1 C2 1.397(5) . ?
N1 C10 1.454(5) . ?
N2 C15 1.325(5) . ?
N2 C11 1.334(5) . ?
N2 Zn1 2.010(3) 3 ?
C1 C8 1.494(5) . ?
C2 C3 1.484(5) . ?
C3 C4 1.381(5) . ?
C3 C8 1.390(5) . ?
C4 C5 1.394(5) . ?
C4 H4 0.9300 . ?
C5 C6 1.394(5) . ?
C5 C9 1.513(4) . ?
C6 C7 1.391(5) . ?
C6 H6 0.9300 . ?
C7 C8 1.371(5) . ?
C7 H7 0.9300 . ?
C10 C13 1.505(5) . ?
C10 H10A 0.9700 . ?
C10 H10B 0.9700 . ?
C11 C12 1.382(5) . ?
C11 H11 0.9300 . ?
C12 C13 1.369(6) . ?
C12 H12 0.9300 . ?
C13 C14 1.385(5) . ?
C14 C15 1.380(5) . ?
C14 H14 0.9300 . ?
C15 H15 0.9300 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
O3 Zn1 O3 104.58(14) . 2 ?
O3 Zn1 N2 106.48(11) . 4_545 ?
O3 Zn1 N2 111.04(11) 2 4_545 ?
O3 Zn1 N2 111.04(11) . 3_445 ?
O3 Zn1 N2 106.48(11) 2 3_445 ?
N2 Zn1 N2 116.62(16) 4_545 3_445 ?
C9 O3 Zn1 110.5(2) . . ?
C1 N1 C2 112.5(3) . . ?
C1 N1 C10 124.6(3) . . ?
C2 N1 C10 122.7(3) . . ?
C15 N2 C11 118.1(3) . . ?
C15 N2 Zn1 125.6(2) . 3 ?
C11 N2 Zn1 116.1(3) . 3 ?
O1 C1 N1 124.6(4) . . ?
O1 C1 C8 129.6(4) . . ?
N1 C1 C8 105.8(3) . . ?
O2 C2 N1 124.3(3) . . ?
O2 C2 C3 130.1(3) . . ?
N1 C2 C3 105.6(3) . . ?
C4 C3 C8 121.6(3) . . ?
C4 C3 C2 130.1(3) . . ?
C8 C3 C2 108.3(3) . . ?
C3 C4 C5 117.5(3) . . ?
C3 C4 H4 121.2 . . ?
C5 C4 H4 121.2 . . ?
C4 C5 C6 120.4(3) . . ?
C4 C5 C9 121.0(3) . . ?
C6 C5 C9 118.7(3) . . ?
C7 C6 C5 121.6(3) . . ?
C7 C6 H6 119.2 . . ?
C5 C6 H6 119.2 . . ?
C8 C7 C6 117.5(3) . . ?
C8 C7 H7 121.3 . . ?
C6 C7 H7 121.3 . . ?
C7 C8 C3 121.4(3) . . ?
C7 C8 C1 130.8(3) . . ?
C3 C8 C1 107.8(3) . . ?
O4 C9 O3 124.7(3) . . ?
O4 C9 C5 119.9(3) . . ?
O3 C9 C5 115.4(3) . . ?
N1 C10 C13 113.0(3) . . ?
N1 C10 H10A 109.0 . . ?
C13 C10 H10A 109.0 . . ?
N1 C10 H10B 109.0 . . ?
C13 C10 H10B 109.0 . . ?
H10A C10 H10B 107.8 . . ?
N2 C11 C12 122.0(4) . . ?
N2 C11 H11 119.0 . . ?
C12 C11 H11 119.0 . . ?
C13 C12 C11 120.0(4) . . ?
C13 C12 H12 120.0 . . ?
C11 C12 H12 120.0 . . ?
C12 C13 C14 118.0(3) . . ?
C12 C13 C10 119.9(3) . . ?
C14 C13 C10 122.1(4) . . ?
C15 C14 C13 118.7(3) . . ?
C15 C14 H14 120.7 . . ?
C13 C14 H14 120.7 . . ?
N2 C15 C14 123.2(3) . . ?
N2 C15 H15 118.4 . . ?
C14 C15 H15 118.4 . . ?

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
O3 Zn1 O3 C9 178.9(3) 2 . . . ?
N2 Zn1 O3 C9 -63.5(3) 4_545 . . . ?
N2 Zn1 O3 C9 64.4(3) 3_445 . . . ?
C2 N1 C1 O1 -178.8(4) . . . . ?
C10 N1 C1 O1 -3.6(6) . . . . ?
C2 N1 C1 C8 0.7(4) . . . . ?
C10 N1 C1 C8 175.9(3) . . . . ?
C1 N1 C2 O2 179.8(3) . . . . ?
C10 N1 C2 O2 4.6(5) . . . . ?
C1 N1 C2 C3 -0.3(4) . . . . ?
C10 N1 C2 C3 -175.5(3) . . . . ?
O2 C2 C3 C4 -1.5(6) . . . . ?
N1 C2 C3 C4 178.6(3) . . . . ?
O2 C2 C3 C8 179.6(4) . . . . ?
N1 C2 C3 C8 -0.3(4) . . . . ?
C8 C3 C4 C5 -0.1(5) . . . . ?
C2 C3 C4 C5 -178.9(3) . . . . ?
C3 C4 C5 C6 -0.7(5) . . . . ?
C3 C4 C5 C9 179.2(3) . . . . ?
C4 C5 C6 C7 1.0(5) . . . . ?
C9 C5 C6 C7 -179.0(3) . . . . ?
C5 C6 C7 C8 -0.3(5) . . . . ?
C6 C7 C8 C3 -0.6(5) . . . . ?
C6 C7 C8 C1 178.3(3) . . . . ?
C4 C3 C8 C7 0.8(5) . . . . ?
C2 C3 C8 C7 179.8(3) . . . . ?
C4 C3 C8 C1 -178.3(3) . . . . ?
C2 C3 C8 C1 0.7(4) . . . . ?
O1 C1 C8 C7 -0.4(7) . . . . ?
N1 C1 C8 C7 -179.9(3) . . . . ?
O1 C1 C8 C3 178.6(4) . . . . ?
N1 C1 C8 C3 -0.9(4) . . . . ?
Zn1 O3 C9 O4 -0.3(4) . . . . ?
Zn1 O3 C9 C5 -179.9(2) . . . . ?
C4 C5 C9 O4 -179.4(3) . . . . ?
C6 C5 C9 O4 0.5(5) . . . . ?
C4 C5 C9 O3 0.2(5) . . . . ?
C6 C5 C9 O3 -179.9(3) . . . . ?
C1 N1 C10 C13 100.8(4) . . . . ?
C2 N1 C10 C13 -84.5(4) . . . . ?
C15 N2 C11 C12 0.6(6) . . . . ?
Zn1 N2 C11 C12 176.1(3) 3 . . . ?
N2 C11 C12 C13 -0.9(7) . . . . ?
C11 C12 C13 C14 0.5(6) . . . . ?
C11 C12 C13 C10 179.1(4) . . . . ?
N1 C10 C13 C12 130.7(4) . . . . ?
N1 C10 C13 C14 -50.7(5) . . . . ?
C12 C13 C14 C15 0.1(5) . . . . ?
C10 C13 C14 C15 -178.4(3) . . . . ?
C11 N2 C15 C14 0.1(5) . . . . ?
Zn1 N2 C15 C14 -174.9(2) 3 . . . ?
C13 C14 C15 N2 -0.4(5) . . . . ?

_diffrn_measured_fraction_theta_max 0.995
_diffrn_reflns_theta_full        26.43
_diffrn_measured_fraction_theta_full 0.995
_refine_diff_density_max         0.877
_refine_diff_density_min         -0.412
_refine_diff_density_rms         0.088
_database_code_depnum_ccdc_archive 'CCDC 973187'
#######################################################################
#
#                 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_cpd_4

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
 ?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C15 H9 Cd Cl N2 O4'
_chemical_formula_weight         429.09

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'
Cd Cd -0.8075 1.2024 '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                   15.146(3)
_cell_length_b                   13.695(3)
_cell_length_c                   6.9265(14)
_cell_angle_alpha                90.00
_cell_angle_beta                 91.28(3)
_cell_angle_gamma                90.00
_cell_volume                     1436.4(5)
_cell_formula_units_Z            4
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    0
_cell_measurement_theta_min      0
_cell_measurement_theta_max      0

_exptl_crystal_description       prism
_exptl_crystal_colour            colorless
_exptl_crystal_size_max          0.45
_exptl_crystal_size_mid          0.40
_exptl_crystal_size_min          0.06
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.984
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             840
_exptl_absorpt_coefficient_mu    1.728
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.5102
_exptl_absorpt_correction_T_max  0.9034
_exptl_absorpt_process_details   ?

_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      296(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  KappaCCD
_diffrn_measurement_method       'CCD rotation images, thick slices'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            5821
_diffrn_reflns_av_R_equivalents  0.0379
_diffrn_reflns_av_sigmaI/netI    0.0488
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_h_max       17
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_l_min       -8
_diffrn_reflns_limit_l_max       8
_diffrn_reflns_theta_min         2.00
_diffrn_reflns_theta_max         25.09
_reflns_number_total             2487
_reflns_number_gt                2054
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'Collect (Nonius BV, 1997-2000)'
_computing_cell_refinement       'HKL Scalepack (Otwinowski & Minor 1997)'
_computing_data_reduction        
'HKL Denzo and Scalepack (Otwinowski&Minor 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    ?
_computing_publication_material  ?

_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)+(0.1119P)²+9.1502P] 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         2487
_refine_ls_number_parameters     208
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0760
_refine_ls_R_factor_gt           0.0621
_refine_ls_wR_factor_ref         0.2167
_refine_ls_wR_factor_gt          0.1969
_refine_ls_goodness_of_fit_ref   1.182
_refine_ls_restrained_S_all      1.182
_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
Cd1 Cd 0.18805(5) 0.81041(5) 0.24596(10) 0.0379(3) Uani 1 1 d . . .
Cl1 Cl 0.0959(2) 0.6856(2) 0.0585(4) 0.0531(7) Uani 1 1 d . . .
O1 O 0.7535(5) 0.6957(5) 0.2940(13) 0.054(2) Uani 1 1 d . . .
O2 O 0.6038(5) 0.9762(5) 0.1585(11) 0.0481(18) Uani 1 1 d . . .
O3 O 0.2886(5) 0.7773(6) -0.0426(11) 0.0495(18) Uani 1 1 d . . .
O4 O 0.3169(5) 0.6254(5) -0.1148(10) 0.0480(17) Uani 1 1 d . . .
N1 N 0.6947(5) 0.8493(6) 0.2540(10) 0.0369(18) Uani 1 1 d . . .
N2 N 0.8506(5) 1.0445(6) -0.1118(11) 0.0387(18) Uani 1 1 d . . .
C1 C 0.6926(6) 0.7480(8) 0.2487(12) 0.035(2) Uani 1 1 d . . .
C2 C 0.6160(6) 0.8907(7) 0.1814(13) 0.037(2) Uani 1 1 d . . .
C3 C 0.5566(7) 0.8063(6) 0.1385(12) 0.032(2) Uani 1 1 d . . .
C4 C 0.4702(7) 0.8050(7) 0.0705(13) 0.037(2) Uani 1 1 d . . .
H4 H 0.4390 0.8623 0.0449 0.045 Uiso 1 1 calc R . .
C5 C 0.4325(6) 0.7141(7) 0.0427(12) 0.033(2) Uani 1 1 d . . .
C6 C 0.4788(7) 0.6290(7) 0.0789(12) 0.038(2) Uani 1 1 d . . .
H6 H 0.4514 0.5693 0.0555 0.046 Uiso 1 1 calc R . .
C7 C 0.5655(6) 0.6305(7) 0.1496(13) 0.037(2) Uani 1 1 d . . .
H7 H 0.5967 0.5734 0.1770 0.044 Uiso 1 1 calc R . .
C8 C 0.6027(6) 0.7218(7) 0.1768(12) 0.0321(19) Uani 1 1 d . . .
C9 C 0.3397(7) 0.7045(7) -0.0418(13) 0.039(2) Uani 1 1 d . . .
C10 C 0.7729(7) 0.9048(8) 0.3152(14) 0.043(2) Uani 1 1 d . . .
H10A H 0.8085 0.8654 0.4036 0.052 Uiso 1 1 calc R . .
H10B H 0.7546 0.9628 0.3839 0.052 Uiso 1 1 calc R . .
C11 C 0.8103(6) 1.0180(7) 0.0486(14) 0.039(2) Uani 1 1 d . . .
H11 H 0.7674 1.0596 0.0962 0.047 Uiso 1 1 calc R . .
C12 C 0.8277(6) 0.9342(7) 0.1479(13) 0.038(2) Uani 1 1 d . . .
C13 C 0.8938(7) 0.8738(8) 0.0803(16) 0.048(3) Uani 1 1 d . . .
H13 H 0.9091 0.8170 0.1465 0.058 Uiso 1 1 calc R . .
C14 C 0.9370(6) 0.8993(8) -0.0874(16) 0.046(2) Uani 1 1 d . . .
H14 H 0.9809 0.8594 -0.1363 0.055 Uiso 1 1 calc R . .
C15 C 0.9136(7) 0.9841(8) -0.1788(15) 0.043(2) Uani 1 1 d . . .
H15 H 0.9420 1.0009 -0.2916 0.052 Uiso 1 1 calc R . .


_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
Cd1 N2 2.265(8) 3_675 ?
Cd1 O4 2.329(7) 4_576 ?
Cd1 O3 2.410(8) 4_576 ?
Cd1 Cl1 2.544(3) . ?
Cd1 O3 2.580(8) . ?
Cd1 Cl1 2.602(3) 4_576 ?
Cd1 C9 2.707(10) 4_576 ?
Cl1 Cd1 2.602(3) 4_575 ?
O1 C1 1.204(12) . ?
O2 C2 1.195(12) . ?
O3 C9 1.262(13) . ?
O3 Cd1 2.410(8) 4_575 ?
O4 C9 1.240(12) . ?
O4 Cd1 2.329(7) 4_575 ?
N1 C1 1.389(14) . ?
N1 C2 1.403(13) . ?
N1 C10 1.462(12) . ?
N2 C11 1.330(12) . ?
N2 C15 1.353(13) . ?
N2 Cd1 2.265(8) 3_675 ?
C1 C8 1.484(13) . ?
C2 C3 1.491(13) . ?
C3 C8 1.374(13) . ?
C3 C4 1.381(14) . ?
C4 C5 1.382(13) . ?
C4 H4 0.9300 . ?
C5 C6 1.380(14) . ?
C5 C9 1.517(14) . ?
C6 C7 1.392(14) . ?
C6 H6 0.9300 . ?
C7 C8 1.383(14) . ?
C7 H7 0.9300 . ?
C9 Cd1 2.707(10) 4_575 ?
C10 C12 1.495(14) . ?
C10 H10A 0.9700 . ?
C10 H10B 0.9700 . ?
C11 C12 1.361(14) . ?
C11 H11 0.9300 . ?
C12 C13 1.388(15) . ?
C13 C14 1.390(15) . ?
C13 H13 0.9300 . ?
C14 C15 1.366(15) . ?
C14 H14 0.9300 . ?
C15 H15 0.9300 . ?

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
N2 Cd1 O4 92.6(3) 3_675 4_576 ?
N2 Cd1 O3 147.2(3) 3_675 4_576 ?
O4 Cd1 O3 54.8(3) 4_576 4_576 ?
N2 Cd1 Cl1 104.2(2) 3_675 . ?
O4 Cd1 Cl1 155.4(2) 4_576 . ?
O3 Cd1 Cl1 107.9(2) 4_576 . ?
N2 Cd1 O3 89.3(3) 3_675 . ?
O4 Cd1 O3 83.3(3) 4_576 . ?
O3 Cd1 O3 90.4(2) 4_576 . ?
Cl1 Cd1 O3 79.21(19) . . ?
N2 Cd1 Cl1 100.6(2) 3_675 4_576 ?
O4 Cd1 Cl1 96.2(2) 4_576 4_576 ?
O3 Cd1 Cl1 81.3(2) 4_576 4_576 ?
Cl1 Cd1 Cl1 98.09(10) . 4_576 ?
O3 Cd1 Cl1 170.06(19) . 4_576 ?
N2 Cd1 C9 119.8(3) 3_675 4_576 ?
O4 Cd1 C9 27.2(3) 4_576 4_576 ?
O3 Cd1 C9 27.8(3) 4_576 4_576 ?
Cl1 Cd1 C9 132.5(2) . 4_576 ?
O3 Cd1 C9 84.2(3) . 4_576 ?
Cl1 Cd1 C9 90.8(2) 4_576 4_576 ?
Cd1 Cl1 Cd1 96.45(10) . 4_575 ?
C9 O3 Cd1 89.3(6) . 4_575 ?
C9 O3 Cd1 120.5(6) . . ?
Cd1 O3 Cd1 100.5(3) 4_575 . ?
C9 O4 Cd1 93.6(6) . 4_575 ?
C1 N1 C2 112.1(8) . . ?
C1 N1 C10 123.0(8) . . ?
C2 N1 C10 124.8(9) . . ?
C11 N2 C15 117.3(9) . . ?
C11 N2 Cd1 117.6(6) . 3_675 ?
C15 N2 Cd1 125.0(7) . 3_675 ?
O1 C1 N1 124.8(9) . . ?
O1 C1 C8 129.5(10) . . ?
N1 C1 C8 105.7(8) . . ?
O2 C2 N1 124.8(9) . . ?
O2 C2 C3 130.0(9) . . ?
N1 C2 C3 105.2(8) . . ?
C8 C3 C4 121.9(9) . . ?
C8 C3 C2 108.2(9) . . ?
C4 C3 C2 129.9(8) . . ?
C3 C4 C5 116.3(9) . . ?
C3 C4 H4 121.8 . . ?
C5 C4 H4 121.8 . . ?
C6 C5 C4 122.0(9) . . ?
C6 C5 C9 117.3(8) . . ?
C4 C5 C9 120.6(9) . . ?
C5 C6 C7 121.5(9) . . ?
C5 C6 H6 119.2 . . ?
C7 C6 H6 119.2 . . ?
C8 C7 C6 116.1(9) . . ?
C8 C7 H7 122.0 . . ?
C6 C7 H7 122.0 . . ?
C3 C8 C7 122.1(9) . . ?
C3 C8 C1 108.7(9) . . ?
C7 C8 C1 129.2(9) . . ?
O4 C9 O3 121.5(10) . . ?
O4 C9 C5 118.7(9) . . ?
O3 C9 C5 119.8(9) . . ?
O4 C9 Cd1 59.2(5) . 4_575 ?
O3 C9 Cd1 62.9(6) . 4_575 ?
C5 C9 Cd1 169.8(6) . 4_575 ?
N1 C10 C12 112.0(8) . . ?
N1 C10 H10A 109.2 . . ?
C12 C10 H10A 109.2 . . ?
N1 C10 H10B 109.2 . . ?
C12 C10 H10B 109.2 . . ?
H10A C10 H10B 107.9 . . ?
N2 C11 C12 124.5(9) . . ?
N2 C11 H11 117.8 . . ?
C12 C11 H11 117.8 . . ?
C11 C12 C13 117.7(9) . . ?
C11 C12 C10 121.0(9) . . ?
C13 C12 C10 121.2(9) . . ?
C12 C13 C14 119.3(10) . . ?
C12 C13 H13 120.4 . . ?
C14 C13 H13 120.4 . . ?
C15 C14 C13 118.6(10) . . ?
C15 C14 H14 120.7 . . ?
C13 C14 H14 120.7 . . ?
N2 C15 C14 122.7(9) . . ?
N2 C15 H15 118.7 . . ?
C14 C15 H15 118.7 . . ?

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
N2 Cd1 Cl1 Cd1 75.0(2) 3_675 . . 4_575 ?
O4 Cd1 Cl1 Cd1 -57.0(5) 4_576 . . 4_575 ?
O3 Cd1 Cl1 Cd1 -98.4(2) 4_576 . . 4_575 ?
O3 Cd1 Cl1 Cd1 -11.49(19) . . . 4_575 ?
Cl1 Cd1 Cl1 Cd1 178.21(9) 4_576 . . 4_575 ?
C9 Cd1 Cl1 Cd1 -83.2(3) 4_576 . . 4_575 ?
N2 Cd1 O3 C9 172.4(8) 3_675 . . . ?
O4 Cd1 O3 C9 79.7(8) 4_576 . . . ?
O3 Cd1 O3 C9 25.2(8) 4_576 . . . ?
Cl1 Cd1 O3 C9 -82.9(8) . . . . ?
Cl1 Cd1 O3 C9 -7.9(16) 4_576 . . . ?
C9 Cd1 O3 C9 52.4(8) 4_576 . . . ?
N2 Cd1 O3 Cd1 -92.1(3) 3_675 . . 4_575 ?
O4 Cd1 O3 Cd1 175.2(3) 4_576 . . 4_575 ?
O3 Cd1 O3 Cd1 120.7(4) 4_576 . . 4_575 ?
Cl1 Cd1 O3 Cd1 12.6(2) . . . 4_575 ?
Cl1 Cd1 O3 Cd1 87.6(10) 4_576 . . 4_575 ?
C9 Cd1 O3 Cd1 147.8(3) 4_576 . . 4_575 ?
C2 N1 C1 O1 176.2(9) . . . . ?
C10 N1 C1 O1 0.4(14) . . . . ?
C2 N1 C1 C8 -3.5(9) . . . . ?
C10 N1 C1 C8 -179.2(7) . . . . ?
C1 N1 C2 O2 -174.6(9) . . . . ?
C10 N1 C2 O2 1.0(14) . . . . ?
C1 N1 C2 C3 4.0(9) . . . . ?
C10 N1 C2 C3 179.7(8) . . . . ?
O2 C2 C3 C8 175.6(9) . . . . ?
N1 C2 C3 C8 -2.9(9) . . . . ?
O2 C2 C3 C4 -3.9(16) . . . . ?
N1 C2 C3 C4 177.6(9) . . . . ?
C8 C3 C4 C5 -0.1(13) . . . . ?
C2 C3 C4 C5 179.3(8) . . . . ?
C3 C4 C5 C6 -0.6(13) . . . . ?
C3 C4 C5 C9 -176.7(8) . . . . ?
C4 C5 C6 C7 1.4(14) . . . . ?
C9 C5 C6 C7 177.6(8) . . . . ?
C5 C6 C7 C8 -1.4(13) . . . . ?
C4 C3 C8 C7 0.1(13) . . . . ?
C2 C3 C8 C7 -179.5(8) . . . . ?
C4 C3 C8 C1 -179.5(8) . . . . ?
C2 C3 C8 C1 0.9(9) . . . . ?
C6 C7 C8 C3 0.7(13) . . . . ?
C6 C7 C8 C1 -179.8(8) . . . . ?
O1 C1 C8 C3 -178.2(10) . . . . ?
N1 C1 C8 C3 1.5(9) . . . . ?
O1 C1 C8 C7 2.2(15) . . . . ?
N1 C1 C8 C7 -178.1(8) . . . . ?
Cd1 O4 C9 O3 9.0(10) 4_575 . . . ?
Cd1 O4 C9 C5 -168.5(7) 4_575 . . . ?
Cd1 O3 C9 O4 -8.7(10) 4_575 . . . ?
Cd1 O3 C9 O4 93.1(10) . . . . ?
Cd1 O3 C9 C5 168.8(7) 4_575 . . . ?
Cd1 O3 C9 C5 -89.4(9) . . . . ?
Cd1 O3 C9 Cd1 101.8(6) . . . 4_575 ?
C6 C5 C9 O4 -16.3(13) . . . . ?
C4 C5 C9 O4 160.0(9) . . . . ?
C6 C5 C9 O3 166.2(9) . . . . ?
C4 C5 C9 O3 -17.6(13) . . . . ?
C6 C5 C9 Cd1 -92(4) . . . 4_575 ?
C4 C5 C9 Cd1 85(4) . . . 4_575 ?
C1 N1 C10 C12 94.2(10) . . . . ?
C2 N1 C10 C12 -81.0(11) . . . . ?
C15 N2 C11 C12 -0.6(14) . . . . ?
Cd1 N2 C11 C12 -178.6(7) 3_675 . . . ?
N2 C11 C12 C13 2.1(15) . . . . ?
N2 C11 C12 C10 -173.6(9) . . . . ?
N1 C10 C12 C11 86.6(11) . . . . ?
N1 C10 C12 C13 -88.9(12) . . . . ?
C11 C12 C13 C14 -2.2(15) . . . . ?
C10 C12 C13 C14 173.5(9) . . . . ?
C12 C13 C14 C15 1.0(15) . . . . ?
C11 N2 C15 C14 -0.8(14) . . . . ?
Cd1 N2 C15 C14 177.1(7) 3_675 . . . ?
C13 C14 C15 N2 0.6(15) . . . . ?

_diffrn_measured_fraction_theta_max 0.970
_diffrn_reflns_theta_full        25.09
_diffrn_measured_fraction_theta_full 0.970
_refine_diff_density_max         1.584
_refine_diff_density_min         -1.365
_refine_diff_density_rms         0.308
_database_code_depnum_ccdc_archive 'CCDC 973188'
#######################################################################
#
#                 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_cpd_5

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
 ?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C30 H22 Cd N4 O10'
_chemical_formula_weight         710.92

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'
Cd Cd -0.8075 1.2024 '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                   6.7987(8)
_cell_length_b                   24.5045(19)
_cell_length_c                   8.2871(10)
_cell_angle_alpha                90.00
_cell_angle_beta                 91.514(11)
_cell_angle_gamma                90.00
_cell_volume                     1380.1(3)
_cell_formula_units_Z            2
_cell_measurement_temperature    150(2)
_cell_measurement_reflns_used    2086
_cell_measurement_theta_min      2.9540
_cell_measurement_theta_max      29.2370

_exptl_crystal_description       prism
_exptl_crystal_colour            colorless
_exptl_crystal_size_max          0.65
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.18
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.711
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             716
_exptl_absorpt_coefficient_mu    0.861
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.87307
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_process_details   
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.24 (release 03-12-2012 CrysAlis171 .NET)
(compiled Dec  3 2012,18:21:49)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;

_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      150(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Xcalibur, Sapphire3, Gemini'
_diffrn_measurement_method       ?
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            6584
_diffrn_reflns_av_R_equivalents  0.0300
_diffrn_reflns_av_sigmaI/netI    0.0497
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_k_min       -33
_diffrn_reflns_limit_k_max       29
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_limit_l_max       9
_diffrn_reflns_theta_min         2.97
_diffrn_reflns_theta_max         29.42
_reflns_number_total             3277
_reflns_number_gt                2789
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.24 (release 03-12-2012 CrysAlis171 .NET)
(compiled Dec  3 2012,18:21:49)
;
_computing_cell_refinement       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.24 (release 03-12-2012 CrysAlis171 .NET)
(compiled Dec  3 2012,18:21:49)
;
_computing_data_reduction        
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.24 (release 03-12-2012 CrysAlis171 .NET)
(compiled Dec  3 2012,18:21:49)
;
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    ?
_computing_publication_material  ?

_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)+(0.0030P)²+3.0446P] 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         3277
_refine_ls_number_parameters     205
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0734
_refine_ls_R_factor_gt           0.0595
_refine_ls_wR_factor_ref         0.0980
_refine_ls_wR_factor_gt          0.0942
_refine_ls_goodness_of_fit_ref   1.330
_refine_ls_restrained_S_all      1.330
_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
Cd1 Cd 0.0000 0.5000 0.5000 0.02288(12) Uani 1 2 d S . .
O1 O 0.2300(5) 0.87808(12) 0.4690(5) 0.0470(10) Uani 1 1 d . . .
O2 O 0.7222(5) 0.77722(13) 0.6956(5) 0.0424(9) Uani 1 1 d . . .
O3 O 0.1005(4) 0.58510(11) 0.4221(4) 0.0267(7) Uani 1 1 d . . .
O4 O 0.4143(5) 0.58213(12) 0.5109(4) 0.0362(8) Uani 1 1 d . . .
O5 O -0.3068(4) 0.51452(11) 0.3733(4) 0.0296(7) Uani 1 1 d . . .
H101 H -0.3886 0.4868 0.3840 0.044 Uiso 1 1 d R . .
H102 H -0.3626 0.5413 0.4186 0.044 Uiso 1 1 d R . .
N1 N 0.4982(5) 0.83914(13) 0.5932(4) 0.0238(8) Uani 1 1 d . . .
N2 N 0.8770(5) 0.96092(13) 0.2255(4) 0.0218(8) Uani 1 1 d . . .
C1 C 0.3201(7) 0.83821(17) 0.5089(6) 0.0286(10) Uani 1 1 d . . .
C2 C 0.5715(7) 0.78735(17) 0.6237(5) 0.0245(9) Uani 1 1 d . . .
C3 C 0.4247(6) 0.74921(16) 0.5506(5) 0.0207(9) Uani 1 1 d . . .
C4 C 0.4261(7) 0.69346(16) 0.5451(5) 0.0251(9) Uani 1 1 d . . .
H4 H 0.5302 0.6735 0.5901 0.030 Uiso 1 1 calc R . .
C5 C 0.2676(6) 0.66798(16) 0.4705(5) 0.0220(9) Uani 1 1 d . . .
C6 C 0.1153(7) 0.69843(17) 0.4019(6) 0.0276(10) Uani 1 1 d . . .
H6 H 0.0095 0.6805 0.3520 0.033 Uiso 1 1 calc R . .
C7 C 0.1169(7) 0.75506(17) 0.4058(6) 0.0316(11) Uani 1 1 d . . .
H7 H 0.0156 0.7754 0.3581 0.038 Uiso 1 1 calc R . .
C8 C 0.2741(7) 0.77974(16) 0.4827(5) 0.0246(9) Uani 1 1 d . . .
C9 C 0.2584(7) 0.60603(16) 0.4682(5) 0.0245(9) Uani 1 1 d . . .
C10 C 0.6002(7) 0.88956(17) 0.6324(6) 0.0318(11) Uani 1 1 d . . .
H10A H 0.6994 0.8825 0.7161 0.038 Uiso 1 1 calc R . .
H10B H 0.5071 0.9156 0.6746 0.038 Uiso 1 1 calc R . .
C11 C 0.8414(7) 0.90718(17) 0.2302(6) 0.0276(10) Uani 1 1 d . . .
H11 H 0.8786 0.8856 0.1440 0.033 Uiso 1 1 calc R . .
C12 C 0.7516(7) 0.88300(17) 0.3588(6) 0.0285(10) Uani 1 1 d . . .
H12 H 0.7278 0.8456 0.3581 0.034 Uiso 1 1 calc R . .
C13 C 0.6971(6) 0.91407(16) 0.4882(5) 0.0232(9) Uani 1 1 d . . .
C14 C 0.7336(7) 0.96909(17) 0.4818(6) 0.0296(11) Uani 1 1 d . . .
H14 H 0.6980 0.9916 0.5666 0.036 Uiso 1 1 calc R . .
C15 C 0.8224(6) 0.99061(16) 0.3502(5) 0.0282(10) Uani 1 1 d . . .
H15 H 0.8457 1.0280 0.3481 0.034 Uiso 1 1 calc R . .


_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
Cd1 N2 2.278(3) 2_645 ?
Cd1 N2 2.278(3) 4_476 ?
Cd1 O3 2.293(3) 3_566 ?
Cd1 O3 2.293(3) . ?
Cd1 O5 2.337(3) . ?
Cd1 O5 2.337(3) 3_566 ?
O1 C1 1.195(5) . ?
O2 C2 1.197(5) . ?
O3 C9 1.241(5) . ?
O4 C9 1.253(5) . ?
O5 H101 0.8843 . ?
O5 H102 0.8496 . ?
N1 C1 1.382(6) . ?
N1 C2 1.384(5) . ?
N1 C10 1.449(5) . ?
N2 C15 1.325(5) . ?
N2 C11 1.340(5) . ?
N2 Cd1 2.278(3) 2_655 ?
C1 C8 1.481(6) . ?
C2 C3 1.485(6) . ?
C3 C4 1.367(5) . ?
C3 C8 1.377(6) . ?
C4 C5 1.378(6) . ?
C4 H4 0.9300 . ?
C5 C6 1.386(6) . ?
C5 C9 1.520(5) . ?
C6 C7 1.388(6) . ?
C6 H6 0.9300 . ?
C7 C8 1.371(6) . ?
C7 H7 0.9300 . ?
C10 C13 1.504(6) . ?
C10 H10A 0.9700 . ?
C10 H10B 0.9700 . ?
C11 C12 1.376(6) . ?
C11 H11 0.9300 . ?
C12 C13 1.374(6) . ?
C12 H12 0.9300 . ?
C13 C14 1.372(5) . ?
C14 C15 1.366(6) . ?
C14 H14 0.9300 . ?
C15 H15 0.9300 . ?

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
N2 Cd1 N2 180.000(1) 2_645 4_476 ?
N2 Cd1 O3 88.13(11) 2_645 3_566 ?
N2 Cd1 O3 91.87(11) 4_476 3_566 ?
N2 Cd1 O3 91.87(11) 2_645 . ?
N2 Cd1 O3 88.13(11) 4_476 . ?
O3 Cd1 O3 180.00(6) 3_566 . ?
N2 Cd1 O5 92.19(12) 2_645 . ?
N2 Cd1 O5 87.81(12) 4_476 . ?
O3 Cd1 O5 89.77(11) 3_566 . ?
O3 Cd1 O5 90.23(11) . . ?
N2 Cd1 O5 87.81(12) 2_645 3_566 ?
N2 Cd1 O5 92.19(12) 4_476 3_566 ?
O3 Cd1 O5 90.23(11) 3_566 3_566 ?
O3 Cd1 O5 89.77(11) . 3_566 ?
O5 Cd1 O5 180.000(1) . 3_566 ?
C9 O3 Cd1 123.4(3) . . ?
Cd1 O5 H101 113.2 . . ?
Cd1 O5 H102 108.9 . . ?
H101 O5 H102 105.0 . . ?
C1 N1 C2 112.5(3) . . ?
C1 N1 C10 122.3(4) . . ?
C2 N1 C10 125.0(4) . . ?
C15 N2 C11 117.6(4) . . ?
C15 N2 Cd1 121.7(3) . 2_655 ?
C11 N2 Cd1 120.5(3) . 2_655 ?
O1 C1 N1 124.2(4) . . ?
O1 C1 C8 130.2(4) . . ?
N1 C1 C8 105.6(4) . . ?
O2 C2 N1 125.4(4) . . ?
O2 C2 C3 129.0(4) . . ?
N1 C2 C3 105.5(4) . . ?
C4 C3 C8 122.4(4) . . ?
C4 C3 C2 129.6(4) . . ?
C8 C3 C2 108.0(3) . . ?
C3 C4 C5 117.5(4) . . ?
C3 C4 H4 121.3 . . ?
C5 C4 H4 121.3 . . ?
C4 C5 C6 120.5(4) . . ?
C4 C5 C9 119.3(4) . . ?
C6 C5 C9 120.2(4) . . ?
C5 C6 C7 121.5(4) . . ?
C5 C6 H6 119.2 . . ?
C7 C6 H6 119.2 . . ?
C8 C7 C6 117.2(4) . . ?
C8 C7 H7 121.4 . . ?
C6 C7 H7 121.4 . . ?
C7 C8 C3 120.9(4) . . ?
C7 C8 C1 130.8(4) . . ?
C3 C8 C1 108.3(4) . . ?
O3 C9 O4 127.7(4) . . ?
O3 C9 C5 116.8(4) . . ?
O4 C9 C5 115.4(4) . . ?
N1 C10 C13 112.3(4) . . ?
N1 C10 H10A 109.1 . . ?
C13 C10 H10A 109.1 . . ?
N1 C10 H10B 109.1 . . ?
C13 C10 H10B 109.1 . . ?
H10A C10 H10B 107.9 . . ?
N2 C11 C12 122.0(4) . . ?
N2 C11 H11 119.0 . . ?
C12 C11 H11 119.0 . . ?
C13 C12 C11 120.0(4) . . ?
C13 C12 H12 120.0 . . ?
C11 C12 H12 120.0 . . ?
C14 C13 C12 117.5(4) . . ?
C14 C13 C10 120.4(4) . . ?
C12 C13 C10 122.1(4) . . ?
C15 C14 C13 119.6(4) . . ?
C15 C14 H14 120.2 . . ?
C13 C14 H14 120.2 . . ?
N2 C15 C14 123.3(4) . . ?
N2 C15 H15 118.3 . . ?
C14 C15 H15 118.3 . . ?

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
N2 Cd1 O3 C9 -95.1(3) 2_645 . . . ?
N2 Cd1 O3 C9 84.9(3) 4_476 . . . ?
O3 Cd1 O3 C9 48(68) 3_566 . . . ?
O5 Cd1 O3 C9 172.7(3) . . . . ?
O5 Cd1 O3 C9 -7.3(3) 3_566 . . . ?
C2 N1 C1 O1 -179.8(5) . . . . ?
C10 N1 C1 O1 -4.2(7) . . . . ?
C2 N1 C1 C8 0.1(5) . . . . ?
C10 N1 C1 C8 175.6(4) . . . . ?
C1 N1 C2 O2 -179.4(5) . . . . ?
C10 N1 C2 O2 5.2(7) . . . . ?
C1 N1 C2 C3 0.2(5) . . . . ?
C10 N1 C2 C3 -175.2(4) . . . . ?
O2 C2 C3 C4 -1.1(8) . . . . ?
N1 C2 C3 C4 179.4(4) . . . . ?
O2 C2 C3 C8 179.1(5) . . . . ?
N1 C2 C3 C8 -0.4(5) . . . . ?
C8 C3 C4 C5 -1.1(7) . . . . ?
C2 C3 C4 C5 179.1(4) . . . . ?
C3 C4 C5 C6 1.1(7) . . . . ?
C3 C4 C5 C9 -177.3(4) . . . . ?
C4 C5 C6 C7 0.0(7) . . . . ?
C9 C5 C6 C7 178.3(4) . . . . ?
C5 C6 C7 C8 -1.0(7) . . . . ?
C6 C7 C8 C3 1.0(7) . . . . ?
C6 C7 C8 C1 -179.7(5) . . . . ?
C4 C3 C8 C7 0.0(7) . . . . ?
C2 C3 C8 C7 179.8(4) . . . . ?
C4 C3 C8 C1 -179.4(4) . . . . ?
C2 C3 C8 C1 0.4(5) . . . . ?
O1 C1 C8 C7 0.2(9) . . . . ?
N1 C1 C8 C7 -179.7(5) . . . . ?
O1 C1 C8 C3 179.5(5) . . . . ?
N1 C1 C8 C3 -0.3(5) . . . . ?
Cd1 O3 C9 O4 27.5(7) . . . . ?
Cd1 O3 C9 C5 -153.9(3) . . . . ?
C4 C5 C9 O3 169.3(4) . . . . ?
C6 C5 C9 O3 -9.1(6) . . . . ?
C4 C5 C9 O4 -11.9(6) . . . . ?
C6 C5 C9 O4 169.7(4) . . . . ?
C1 N1 C10 C13 -75.1(5) . . . . ?
C2 N1 C10 C13 99.9(5) . . . . ?
C15 N2 C11 C12 0.0(7) . . . . ?
Cd1 N2 C11 C12 -174.3(4) 2_655 . . . ?
N2 C11 C12 C13 -0.6(7) . . . . ?
C11 C12 C13 C14 0.8(7) . . . . ?
C11 C12 C13 C10 -179.5(5) . . . . ?
N1 C10 C13 C14 154.9(4) . . . . ?
N1 C10 C13 C12 -24.8(6) . . . . ?
C12 C13 C14 C15 -0.5(7) . . . . ?
C10 C13 C14 C15 179.8(4) . . . . ?
C11 N2 C15 C14 0.3(7) . . . . ?
Cd1 N2 C15 C14 174.6(4) 2_655 . . . ?
C13 C14 C15 N2 -0.1(8) . . . . ?

_diffrn_measured_fraction_theta_max 0.859
_diffrn_reflns_theta_full        26.00
_diffrn_measured_fraction_theta_full 0.999
_refine_diff_density_max         0.459
_refine_diff_density_min         -0.388
_refine_diff_density_rms         0.092
_database_code_depnum_ccdc_archive 'CCDC 973189'
