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

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#
#                 Cambridge Crystallographic Data Centre
#                                CCDC 
# 
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# 
#  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
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#  data retrieval see:
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#  from this site to visualise CIF-encoded structures and 
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data_967570

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C14 H18 N2 Ni O7'
_chemical_formula_weight         385.01

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'
Ni Ni 0.3393 1.1124 '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                   26.4001(12)
_cell_length_b                   8.6506(4)
_cell_length_c                   16.5796(8)
_cell_angle_alpha                90.00
_cell_angle_beta                 115.8980(10)
_cell_angle_gamma                90.00
_cell_volume                     3406.1(3)
_cell_formula_units_Z            8
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    3895
_cell_measurement_theta_min      2.51
_cell_measurement_theta_max      29.04

_exptl_crystal_description       BLOCK
_exptl_crystal_colour            GREEN
_exptl_crystal_size_max          0.38
_exptl_crystal_size_mid          0.32
_exptl_crystal_size_min          0.20
_exptl_crystal_density_meas      NONE
_exptl_crystal_density_diffrn    1.502
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1600
_exptl_absorpt_coefficient_mu    1.176
_exptl_absorpt_correction_type   MULTI-SCAN
_exptl_absorpt_correction_T_min  0.6634
_exptl_absorpt_correction_T_max  0.7987
_exptl_absorpt_process_details   SADABS

_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  '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            8475
_diffrn_reflns_av_R_equivalents  0.0199
_diffrn_reflns_av_sigmaI/netI    0.0226
_diffrn_reflns_limit_h_min       -31
_diffrn_reflns_limit_h_max       29
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_k_max       4
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_theta_min         1.71
_diffrn_reflns_theta_max         25.03
_reflns_number_total             3015
_reflns_number_gt                2653
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'Bruker SMART'
_computing_cell_refinement       'Bruker SMART'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'

_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)+(0.0357P)²+3.0544P] 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         3015
_refine_ls_number_parameters     222
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0308
_refine_ls_R_factor_gt           0.0255
_refine_ls_wR_factor_ref         0.0694
_refine_ls_wR_factor_gt          0.0663
_refine_ls_goodness_of_fit_ref   1.036
_refine_ls_restrained_S_all      1.036
_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
Ni1 Ni 0.0000 0.5000 0.0000 0.02191(11) Uani 1 2 d S . .
Ni2 Ni 0.2500 0.7500 0.5000 0.01983(11) Uani 1 2 d S . .
O1 O -0.17072(5) 0.79906(16) 0.02071(9) 0.0281(3) Uani 1 1 d . . .
O2 O -0.15437(7) 1.04525(19) 0.06354(13) 0.0486(5) Uani 1 1 d . . .
O3 O 0.07560(6) 0.46913(19) 0.22412(10) 0.0383(4) Uani 1 1 d . . .
O4 O 0.08125(5) 0.50941(17) 0.09507(9) 0.0287(3) Uani 1 1 d . . .
O5 O -0.02433(6) 0.38703(17) 0.08811(9) 0.0319(3) Uani 1 1 d . . .
H5A H -0.0569 0.3931 0.0865 0.048 Uiso 1 1 d R . .
H5B H 0.0030 0.4034 0.1391 0.048 Uiso 1 1 d R . .
O6 O 0.26622(6) 0.98234(16) 0.48193(10) 0.0306(3) Uani 1 1 d . . .
H6A H 0.2950 1.0359 0.5140 0.046 Uiso 1 1 d R . .
H6B H 0.2343 1.0232 0.4689 0.046 Uiso 1 1 d R . .
O7 O 0.86992(6) 0.35926(18) 0.09555(10) 0.0375(4) Uani 1 1 d . . .
H7A H 0.8660 0.2619 0.0884 0.056 Uiso 1 1 d R . .
H7B H 0.8842 0.3905 0.1496 0.056 Uiso 1 1 d R . .
N1 N -0.01472(7) 0.7162(2) 0.04477(11) 0.0262(4) Uani 1 1 d . . .
N2 N 0.22228(7) 0.7158(2) 0.36272(11) 0.0259(4) Uani 1 1 d . . .
C1 C -0.06616(8) 0.7507(2) 0.03624(13) 0.0269(4) Uani 1 1 d . . .
H1 H -0.0947 0.6786 0.0090 0.032 Uiso 1 1 calc R . .
C2 C -0.07923(8) 0.8881(2) 0.06572(13) 0.0262(4) Uani 1 1 d . . .
C3 C -0.03607(9) 0.9931(2) 0.10891(15) 0.0306(5) Uani 1 1 d . . .
H3 H -0.0434 1.0862 0.1298 0.037 Uiso 1 1 calc R . .
C4 C 0.01816(9) 0.9587(2) 0.12081(15) 0.0300(5) Uani 1 1 d . . .
C5 C 0.02589(8) 0.8214(2) 0.08542(13) 0.0280(5) Uani 1 1 d . . .
H5 H 0.0616 0.8004 0.0900 0.034 Uiso 1 1 calc R . .
C6 C -0.13944(8) 0.9154(2) 0.04921(13) 0.0268(4) Uani 1 1 d . . .
C7 C 0.06739(9) 1.0656(3) 0.16989(18) 0.0458(6) Uani 1 1 d . . .
H7A' H 0.0846 1.0404 0.2326 0.069 Uiso 1 1 calc R . .
H7B' H 0.0544 1.1707 0.1621 0.069 Uiso 1 1 calc R . .
H7C' H 0.0945 1.0538 0.1462 0.069 Uiso 1 1 calc R . .
C8 C 0.25514(9) 0.7439(3) 0.32196(14) 0.0333(5) Uani 1 1 d . . .
H8 H 0.2899 0.7902 0.3551 0.040 Uiso 1 1 calc R . .
C9 C 0.24041(10) 0.7082(3) 0.23299(15) 0.0365(5) Uani 1 1 d . . .
C10 C 0.18845(9) 0.6369(3) 0.18491(14) 0.0328(5) Uani 1 1 d . . .
H10 H 0.1767 0.6115 0.1249 0.039 Uiso 1 1 calc R . .
C11 C 0.15442(8) 0.6041(2) 0.22662(13) 0.0249(4) Uani 1 1 d . . .
C12 C 0.17256(8) 0.6481(2) 0.31517(13) 0.0254(4) Uani 1 1 d . . .
H12 H 0.1491 0.6298 0.3428 0.031 Uiso 1 1 calc R . .
C13 C 0.09923(8) 0.5199(2) 0.17882(13) 0.0255(4) Uani 1 1 d . . .
C14 C 0.27973(13) 0.7434(4) 0.19127(19) 0.0645(9) Uani 1 1 d . . .
H14A H 0.3145 0.7834 0.2362 0.097 Uiso 1 1 calc R . .
H14B H 0.2627 0.8187 0.1446 0.097 Uiso 1 1 calc R . .
H14C H 0.2870 0.6504 0.1664 0.097 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
Ni1 O4 2.0343(13) . ?
Ni1 O4 2.0343(13) 5_565 ?
Ni1 O5 2.0787(14) 5_565 ?
Ni1 O5 2.0787(14) . ?
Ni1 N1 2.1101(17) . ?
Ni1 N1 2.1101(17) 5_565 ?
Ni2 O1 2.0126(13) 2 ?
Ni2 O1 2.0126(13) 8_566 ?
Ni2 N2 2.0852(16) 7_566 ?
Ni2 N2 2.0852(16) . ?
Ni2 O6 2.1035(14) 7_566 ?
Ni2 O6 2.1035(14) . ?
O1 C6 1.256(2) . ?
O1 Ni2 2.0126(13) 2 ?
O2 C6 1.247(3) . ?
O3 C13 1.247(3) . ?
O4 C13 1.259(2) . ?
O5 H5A 0.8500 . ?
O5 H5B 0.8501 . ?
O6 H6A 0.8500 . ?
O6 H6B 0.8500 . ?
O7 H7A 0.8501 . ?
O7 H7B 0.8500 . ?
N1 C1 1.336(3) . ?
N1 C5 1.342(3) . ?
N2 C8 1.334(3) . ?
N2 C12 1.335(2) . ?
C1 C2 1.385(3) . ?
C1 H1 0.9300 . ?
C2 C3 1.387(3) . ?
C2 C6 1.509(3) . ?
C3 C4 1.389(3) . ?
C3 H3 0.9300 . ?
C4 C5 1.378(3) . ?
C4 C7 1.511(3) . ?
C5 H5 0.9300 . ?
C7 H7A' 0.9600 . ?
C7 H7B' 0.9600 . ?
C7 H7C' 0.9600 . ?
C8 C9 1.386(3) . ?
C8 H8 0.9300 . ?
C9 C10 1.394(3) . ?
C9 C14 1.509(3) . ?
C10 C11 1.382(3) . ?
C10 H10 0.9300 . ?
C11 C12 1.384(3) . ?
C11 C13 1.507(3) . ?
C12 H12 0.9300 . ?
C14 H14A 0.9600 . ?
C14 H14B 0.9600 . ?
C14 H14C 0.9600 . ?

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 Ni1 O4 180.00(6) . 5_565 ?
O4 Ni1 O5 88.90(6) . 5_565 ?
O4 Ni1 O5 91.10(6) 5_565 5_565 ?
O4 Ni1 O5 91.10(6) . . ?
O4 Ni1 O5 88.90(6) 5_565 . ?
O5 Ni1 O5 180.00(6) 5_565 . ?
O4 Ni1 N1 89.19(6) . . ?
O4 Ni1 N1 90.81(6) 5_565 . ?
O5 Ni1 N1 89.51(6) 5_565 . ?
O5 Ni1 N1 90.49(6) . . ?
O4 Ni1 N1 90.81(6) . 5_565 ?
O4 Ni1 N1 89.19(6) 5_565 5_565 ?
O5 Ni1 N1 90.49(6) 5_565 5_565 ?
O5 Ni1 N1 89.51(6) . 5_565 ?
N1 Ni1 N1 180.00(9) . 5_565 ?
O1 Ni2 O1 180.00(8) 2 8_566 ?
O1 Ni2 N2 89.96(6) 2 7_566 ?
O1 Ni2 N2 90.04(6) 8_566 7_566 ?
O1 Ni2 N2 90.04(6) 2 . ?
O1 Ni2 N2 89.96(6) 8_566 . ?
N2 Ni2 N2 180.0 7_566 . ?
O1 Ni2 O6 87.97(6) 2 7_566 ?
O1 Ni2 O6 92.03(6) 8_566 7_566 ?
N2 Ni2 O6 88.64(6) 7_566 7_566 ?
N2 Ni2 O6 91.36(6) . 7_566 ?
O1 Ni2 O6 92.03(6) 2 . ?
O1 Ni2 O6 87.97(6) 8_566 . ?
N2 Ni2 O6 91.36(6) 7_566 . ?
N2 Ni2 O6 88.64(6) . . ?
O6 Ni2 O6 180.00(9) 7_566 . ?
C6 O1 Ni2 134.19(13) . 2 ?
C13 O4 Ni1 128.26(13) . . ?
Ni1 O5 H5A 124.6 . . ?
Ni1 O5 H5B 103.5 . . ?
H5A O5 H5B 115.3 . . ?
Ni2 O6 H6A 127.9 . . ?
Ni2 O6 H6B 101.1 . . ?
H6A O6 H6B 116.8 . . ?
H7A O7 H7B 115.7 . . ?
C1 N1 C5 116.97(17) . . ?
C1 N1 Ni1 119.71(13) . . ?
C5 N1 Ni1 123.26(13) . . ?
C8 N2 C12 118.01(17) . . ?
C8 N2 Ni2 122.09(13) . . ?
C12 N2 Ni2 119.50(13) . . ?
N1 C1 C2 123.56(18) . . ?
N1 C1 H1 118.2 . . ?
C2 C1 H1 118.2 . . ?
C1 C2 C3 117.96(18) . . ?
C1 C2 C6 118.38(18) . . ?
C3 C2 C6 123.66(19) . . ?
C2 C3 C4 119.76(19) . . ?
C2 C3 H3 120.1 . . ?
C4 C3 H3 120.1 . . ?
C5 C4 C3 117.33(19) . . ?
C5 C4 C7 120.28(19) . . ?
C3 C4 C7 122.4(2) . . ?
N1 C5 C4 124.31(18) . . ?
N1 C5 H5 117.8 . . ?
C4 C5 H5 117.8 . . ?
O2 C6 O1 125.65(18) . . ?
O2 C6 C2 120.12(18) . . ?
O1 C6 C2 114.23(18) . . ?
C4 C7 H7A' 109.5 . . ?
C4 C7 H7B' 109.5 . . ?
H7A' C7 H7B' 109.5 . . ?
C4 C7 H7C' 109.5 . . ?
H7A' C7 H7C' 109.5 . . ?
H7B' C7 H7C' 109.5 . . ?
N2 C8 C9 123.79(19) . . ?
N2 C8 H8 118.1 . . ?
C9 C8 H8 118.1 . . ?
C8 C9 C10 117.12(19) . . ?
C8 C9 C14 120.9(2) . . ?
C10 C9 C14 122.0(2) . . ?
C11 C10 C9 119.83(19) . . ?
C11 C10 H10 120.1 . . ?
C9 C10 H10 120.1 . . ?
C10 C11 C12 118.35(17) . . ?
C10 C11 C13 121.78(17) . . ?
C12 C11 C13 119.87(18) . . ?
N2 C12 C11 122.86(18) . . ?
N2 C12 H12 118.6 . . ?
C11 C12 H12 118.6 . . ?
O3 C13 O4 126.28(18) . . ?
O3 C13 C11 118.44(17) . . ?
O4 C13 C11 115.27(18) . . ?
C9 C14 H14A 109.5 . . ?
C9 C14 H14B 109.5 . . ?
H14A C14 H14B 109.5 . . ?
C9 C14 H14C 109.5 . . ?
H14A C14 H14C 109.5 . . ?
H14B C14 H14C 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

O5 Ni1 O4 C13 148.51(17) 5_565 . . . ?
O5 Ni1 O4 C13 -31.49(17) . . . . ?
N1 Ni1 O4 C13 58.98(17) . . . . ?
N1 Ni1 O4 C13 -121.02(17) 5_565 . . . ?
O4 Ni1 N1 C1 -150.92(16) . . . . ?
O4 Ni1 N1 C1 29.08(16) 5_565 . . . ?
O5 Ni1 N1 C1 120.17(15) 5_565 . . . ?
O5 Ni1 N1 C1 -59.83(15) . . . . ?
O4 Ni1 N1 C5 26.36(17) . . . . ?
O4 Ni1 N1 C5 -153.64(17) 5_565 . . . ?
O5 Ni1 N1 C5 -62.55(16) 5_565 . . . ?
O5 Ni1 N1 C5 117.45(16) . . . . ?
O1 Ni2 N2 C8 149.83(17) 2 . . . ?
O1 Ni2 N2 C8 -30.17(17) 8_566 . . . ?
O6 Ni2 N2 C8 -122.20(17) 7_566 . . . ?
O6 Ni2 N2 C8 57.80(17) . . . . ?
O1 Ni2 N2 C12 -37.62(16) 2 . . . ?
O1 Ni2 N2 C12 142.38(16) 8_566 . . . ?
O6 Ni2 N2 C12 50.35(16) 7_566 . . . ?
O6 Ni2 N2 C12 -129.65(16) . . . . ?
C5 N1 C1 C2 0.9(3) . . . . ?
Ni1 N1 C1 C2 178.37(15) . . . . ?
N1 C1 C2 C3 -2.1(3) . . . . ?
N1 C1 C2 C6 177.92(18) . . . . ?
C1 C2 C3 C4 0.4(3) . . . . ?
C6 C2 C3 C4 -179.7(2) . . . . ?
C2 C3 C4 C5 2.3(3) . . . . ?
C2 C3 C4 C7 -178.0(2) . . . . ?
C1 N1 C5 C4 2.1(3) . . . . ?
Ni1 N1 C5 C4 -175.26(16) . . . . ?
C3 C4 C5 N1 -3.7(3) . . . . ?
C7 C4 C5 N1 176.6(2) . . . . ?
Ni2 O1 C6 O2 -9.0(3) 2 . . . ?
Ni2 O1 C6 C2 171.36(13) 2 . . . ?
C1 C2 C6 O2 -170.2(2) . . . . ?
C3 C2 C6 O2 9.8(3) . . . . ?
C1 C2 C6 O1 9.5(3) . . . . ?
C3 C2 C6 O1 -170.5(2) . . . . ?
C12 N2 C8 C9 0.6(3) . . . . ?
Ni2 N2 C8 C9 173.25(19) . . . . ?
N2 C8 C9 C10 -0.9(4) . . . . ?
N2 C8 C9 C14 180.0(3) . . . . ?
C8 C9 C10 C11 -0.5(3) . . . . ?
C14 C9 C10 C11 178.6(3) . . . . ?
C9 C10 C11 C12 2.0(3) . . . . ?
C9 C10 C11 C13 -176.8(2) . . . . ?
C8 N2 C12 C11 1.1(3) . . . . ?
Ni2 N2 C12 C11 -171.72(15) . . . . ?
C10 C11 C12 N2 -2.4(3) . . . . ?
C13 C11 C12 N2 176.46(18) . . . . ?
Ni1 O4 C13 O3 29.8(3) . . . . ?
Ni1 O4 C13 C11 -149.57(14) . . . . ?
C10 C11 C13 O3 167.1(2) . . . . ?
C12 C11 C13 O3 -11.8(3) . . . . ?
C10 C11 C13 O4 -13.5(3) . . . . ?
C12 C11 C13 O4 167.64(19) . . . . ?

_diffrn_measured_fraction_theta_max 0.999
_diffrn_reflns_theta_full        25.03
_diffrn_measured_fraction_theta_full 0.999
_refine_diff_density_max         0.425
_refine_diff_density_min         -0.259
_refine_diff_density_rms         0.049
_database_code_depnum_ccdc_archive 'CCDC 967570'
#######################################################################
#
#                 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.
#
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#  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.
# 
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#  data retrieval see:
#                         www.ccdc.cam.ac.uk
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#  from this site to visualise CIF-encoded structures and 
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data_967571

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C28 H26 N4 Ni2 O9'
_chemical_formula_weight         679.95

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'
Ni Ni 0.3393 1.1124 '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                   17.3192(14)
_cell_length_b                   14.3739(12)
_cell_length_c                   23.819(2)
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_volume                     5929.7(9)
_cell_formula_units_Z            8
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    3754
_cell_measurement_theta_min      2.51
_cell_measurement_theta_max      24.98

_exptl_crystal_description       BLOCK
_exptl_crystal_colour            GREEN
_exptl_crystal_size_max          0.28
_exptl_crystal_size_mid          0.22
_exptl_crystal_size_min          0.20
_exptl_crystal_density_meas      NONE
_exptl_crystal_density_diffrn    1.523
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             2800
_exptl_absorpt_coefficient_mu    1.329
_exptl_absorpt_correction_type   MULTI-SCAN
_exptl_absorpt_correction_T_min  0.7073
_exptl_absorpt_correction_T_max  0.7770
_exptl_absorpt_process_details   SADABS

_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  '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            29031
_diffrn_reflns_av_R_equivalents  0.0691
_diffrn_reflns_av_sigmaI/netI    0.0490
_diffrn_reflns_limit_h_min       -20
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_l_min       -28
_diffrn_reflns_limit_l_max       28
_diffrn_reflns_theta_min         1.71
_diffrn_reflns_theta_max         25.03
_reflns_number_total             5231
_reflns_number_gt                3627
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'Bruker SMART'
_computing_cell_refinement       'Bruker SMART'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'

_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)+(0.0316P)²+2.8198P] 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         5231
_refine_ls_number_parameters     392
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0680
_refine_ls_R_factor_gt           0.0344
_refine_ls_wR_factor_ref         0.0799
_refine_ls_wR_factor_gt          0.0677
_refine_ls_goodness_of_fit_ref   1.025
_refine_ls_restrained_S_all      1.025
_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
Ni1 Ni 0.36933(2) 0.96077(2) 0.319433(16) 0.01649(11) Uani 1 1 d . . .
Ni2 Ni 0.37183(2) 0.78070(2) 0.421486(15) 0.01689(11) Uani 1 1 d . . .
O1 O 0.49008(14) 1.22905(14) 0.17543(10) 0.0331(6) Uani 1 1 d . . .
O2 O 0.58007(13) 1.16481(14) 0.12049(9) 0.0238(5) Uani 1 1 d . . .
O3 O 0.17031(12) 1.34345(14) 0.28013(8) 0.0216(5) Uani 1 1 d . . .
O4 O 0.20985(13) 1.27186(14) 0.35915(9) 0.0215(5) Uani 1 1 d . . .
O5 O 0.49151(14) 0.99775(15) 0.58563(11) 0.0379(7) Uani 1 1 d . . .
O6 O 0.58337(13) 0.92605(14) 0.63559(9) 0.0264(6) Uani 1 1 d . . .
O7 O 0.32664(12) 0.89735(14) 0.46013(8) 0.0200(5) Uani 1 1 d . . .
O8 O 0.28461(13) 0.96748(14) 0.38169(9) 0.0218(5) Uani 1 1 d . . .
O9 O 0.43731(12) 0.86911(13) 0.36968(8) 0.0196(5) Uani 1 1 d . . .
H9A H 0.4631 0.9100 0.3874 0.029 Uiso 1 1 d R . .
H9B H 0.4631 0.8273 0.3528 0.029 Uiso 1 1 d R . .
N1 N 0.45380(15) 0.97837(17) 0.25710(11) 0.0208(6) Uani 1 1 d . . .
N2 N 0.29562(15) 1.04920(16) 0.27517(10) 0.0182(6) Uani 1 1 d . . .
N3 N 0.20041(15) 1.19092(17) 0.46686(11) 0.0199(6) Uani 1 1 d . . .
N4 N 0.45714(15) 0.77436(17) 0.48377(11) 0.0222(6) Uani 1 1 d . . .
C1 C 0.53184(19) 1.1631(2) 0.16004(13) 0.0209(7) Uani 1 1 d . . .
C2 C 0.52457(19) 1.0719(2) 0.19174(13) 0.0203(8) Uani 1 1 d . . .
C3 C 0.46610(19) 1.0591(2) 0.23021(14) 0.0229(8) Uani 1 1 d . . .
H3 H 0.4335 1.1089 0.2379 0.027 Uiso 1 1 calc R . .
C4 C 0.5027(2) 0.9085(2) 0.24598(14) 0.0291(9) Uani 1 1 d . . .
H4 H 0.4936 0.8513 0.2630 0.035 Uiso 1 1 calc R . .
C5 C 0.5658(2) 0.9161(2) 0.21095(15) 0.0323(9) Uani 1 1 d . . .
C6 C 0.5760(2) 0.9999(2) 0.18306(14) 0.0287(8) Uani 1 1 d . . .
H6 H 0.6174 1.0075 0.1586 0.034 Uiso 1 1 calc R . .
C7 C 0.6208(3) 0.8360(3) 0.20533(19) 0.0603(14) Uani 1 1 d . . .
H7A H 0.6506 0.8302 0.2392 0.090 Uiso 1 1 calc R . .
H7B H 0.6548 0.8469 0.1742 0.090 Uiso 1 1 calc R . .
H7C H 0.5923 0.7797 0.1991 0.090 Uiso 1 1 calc R . .
C8 C 0.19924(17) 1.2764(2) 0.30739(13) 0.0167(7) Uani 1 1 d . . .
C9 C 0.22405(18) 1.1923(2) 0.27433(13) 0.0183(7) Uani 1 1 d . . .
C10 C 0.27263(18) 1.1280(2) 0.29998(13) 0.0197(7) Uani 1 1 d . . .
H10 H 0.2900 1.1404 0.3362 0.024 Uiso 1 1 calc R . .
C11 C 0.2689(2) 1.0319(2) 0.22338(14) 0.0270(8) Uani 1 1 d . . .
H11 H 0.2836 0.9767 0.2061 0.032 Uiso 1 1 calc R . .
C12 C 0.2207(2) 1.0915(2) 0.19410(14) 0.0354(10) Uani 1 1 d . . .
C13 C 0.1989(2) 1.1737(2) 0.22079(14) 0.0289(9) Uani 1 1 d . . .
H13 H 0.1673 1.2160 0.2023 0.035 Uiso 1 1 calc R . .
C14 C 0.1933(3) 1.0677(3) 0.13555(17) 0.0708(17) Uani 1 1 d . . .
H14A H 0.2336 1.0356 0.1158 0.106 Uiso 1 1 calc R . .
H14B H 0.1804 1.1239 0.1159 0.106 Uiso 1 1 calc R . .
H14C H 0.1485 1.0286 0.1379 0.106 Uiso 1 1 calc R . .
C15 C 0.5338(2) 0.9296(2) 0.59735(14) 0.0239(8) Uani 1 1 d . . .
C16 C 0.52447(19) 0.8446(2) 0.56090(14) 0.0220(7) Uani 1 1 d . . .
C17 C 0.5706(2) 0.7667(2) 0.56534(15) 0.0339(9) Uani 1 1 d . . .
H17 H 0.6094 0.7649 0.5923 0.041 Uiso 1 1 calc R . .
C18 C 0.5598(2) 0.6915(2) 0.53021(16) 0.0381(10) Uani 1 1 d . . .
C19 C 0.5016(2) 0.6986(2) 0.49059(15) 0.0313(9) Uani 1 1 d . . .
H19 H 0.4928 0.6478 0.4673 0.038 Uiso 1 1 calc R . .
C20 C 0.46922(19) 0.8455(2) 0.51874(13) 0.0225(8) Uani 1 1 d . . .
H20 H 0.4390 0.8986 0.5146 0.027 Uiso 1 1 calc R . .
C21 C 0.6094(3) 0.6053(3) 0.5333(2) 0.0723(17) Uani 1 1 d . . .
H21A H 0.6264 0.5887 0.4963 0.108 Uiso 1 1 calc R . .
H21B H 0.5800 0.5551 0.5490 0.108 Uiso 1 1 calc R . .
H21C H 0.6535 0.6173 0.5567 0.108 Uiso 1 1 calc R . .
C22 C 0.29685(18) 0.9643(2) 0.43309(13) 0.0188(7) Uani 1 1 d . . .
C23 C 0.27459(18) 1.0498(2) 0.46618(12) 0.0171(7) Uani 1 1 d . . .
C24 C 0.22076(18) 1.1102(2) 0.44320(13) 0.0199(7) Uani 1 1 d . . .
H24 H 0.1975 1.0936 0.4095 0.024 Uiso 1 1 calc R . .
C25 C 0.2355(2) 1.2144(2) 0.51512(14) 0.0265(8) Uani 1 1 d . . .
H25 H 0.2217 1.2704 0.5319 0.032 Uiso 1 1 calc R . .
C26 C 0.2912(2) 1.1599(2) 0.54142(14) 0.0293(9) Uani 1 1 d . . .
C27 C 0.3102(2) 1.0754(2) 0.51595(13) 0.0255(8) Uani 1 1 d . . .
H27 H 0.3466 1.0364 0.5323 0.031 Uiso 1 1 calc R . .
C28 C 0.3302(3) 1.1927(3) 0.59468(16) 0.0539(12) Uani 1 1 d . . .
H28A H 0.3345 1.2592 0.5941 0.081 Uiso 1 1 calc R . .
H28B H 0.3808 1.1657 0.5971 0.081 Uiso 1 1 calc R . .
H28C H 0.3001 1.1739 0.6266 0.081 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
Ni1 O3 2.047(2) 8_655 ?
Ni1 N2 2.087(2) . ?
Ni1 O8 2.088(2) . ?
Ni1 N1 2.100(3) . ?
Ni1 O6 2.113(2) 5_676 ?
Ni1 O9 2.134(2) . ?
Ni2 O4 2.055(2) 8_655 ?
Ni2 O7 2.067(2) . ?
Ni2 N4 2.096(3) . ?
Ni2 N3 2.097(3) 8_655 ?
Ni2 O9 2.103(2) . ?
Ni2 O2 2.114(2) 3_645 ?
O1 C1 1.248(4) . ?
O2 C1 1.259(4) . ?
O2 Ni2 2.114(2) 3_655 ?
O3 C8 1.265(3) . ?
O3 Ni1 2.047(2) 8_665 ?
O4 C8 1.248(3) . ?
O4 Ni2 2.055(2) 8_665 ?
O5 C15 1.254(4) . ?
O6 C15 1.253(4) . ?
O6 Ni1 2.113(2) 5_676 ?
O7 C22 1.267(3) . ?
O8 C22 1.243(4) . ?
O9 H9A 0.8499 . ?
O9 H9B 0.8501 . ?
N1 C4 1.340(4) . ?
N1 C3 1.342(4) . ?
N2 C10 1.338(4) . ?
N2 C11 1.341(4) . ?
N3 C24 1.337(4) . ?
N3 C25 1.343(4) . ?
N3 Ni2 2.097(3) 8_665 ?
N4 C20 1.336(4) . ?
N4 C19 1.345(4) . ?
C1 C2 1.518(4) . ?
C2 C3 1.378(4) . ?
C2 C6 1.382(4) . ?
C3 H3 0.9300 . ?
C4 C5 1.378(5) . ?
C4 H4 0.9300 . ?
C5 C6 1.386(4) . ?
C5 C7 1.501(5) . ?
C6 H6 0.9300 . ?
C7 H7A 0.9600 . ?
C7 H7B 0.9600 . ?
C7 H7C 0.9600 . ?
C8 C9 1.506(4) . ?
C9 C13 1.374(4) . ?
C9 C10 1.391(4) . ?
C10 H10 0.9300 . ?
C11 C12 1.384(5) . ?
C11 H11 0.9300 . ?
C12 C13 1.394(4) . ?
C12 C14 1.512(5) . ?
C13 H13 0.9300 . ?
C14 H14A 0.9600 . ?
C14 H14B 0.9600 . ?
C14 H14C 0.9600 . ?
C15 C16 1.508(4) . ?
C16 C17 1.379(4) . ?
C16 C20 1.387(4) . ?
C17 C18 1.380(5) . ?
C17 H17 0.9300 . ?
C18 C19 1.385(5) . ?
C18 C21 1.509(5) . ?
C19 H19 0.9300 . ?
C20 H20 0.9300 . ?
C21 H21A 0.9600 . ?
C21 H21B 0.9600 . ?
C21 H21C 0.9600 . ?
C22 C23 1.511(4) . ?
C23 C27 1.386(4) . ?
C23 C24 1.386(4) . ?
C24 H24 0.9300 . ?
C25 C26 1.392(4) . ?
C25 H25 0.9300 . ?
C26 C27 1.397(4) . ?
C26 C28 1.513(5) . ?
C27 H27 0.9300 . ?
C28 H28A 0.9600 . ?
C28 H28B 0.9600 . ?
C28 H28C 0.9600 . ?

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 Ni1 N2 93.76(9) 8_655 . ?
O3 Ni1 O8 97.30(8) 8_655 . ?
N2 Ni1 O8 84.31(9) . . ?
O3 Ni1 N1 90.55(9) 8_655 . ?
N2 Ni1 N1 89.75(10) . . ?
O8 Ni1 N1 170.43(9) . . ?
O3 Ni1 O6 174.84(9) 8_655 5_676 ?
N2 Ni1 O6 91.39(9) . 5_676 ?
O8 Ni1 O6 82.92(9) . 5_676 ?
N1 Ni1 O6 89.75(9) . 5_676 ?
O3 Ni1 O9 86.15(8) 8_655 . ?
N2 Ni1 O9 175.28(9) . . ?
O8 Ni1 O9 91.02(8) . . ?
N1 Ni1 O9 94.97(9) . . ?
O6 Ni1 O9 88.69(8) 5_676 . ?
O4 Ni2 O7 96.39(8) 8_655 . ?
O4 Ni2 N4 173.83(9) 8_655 . ?
O7 Ni2 N4 89.25(9) . . ?
O4 Ni2 N3 85.62(9) 8_655 8_655 ?
O7 Ni2 N3 92.51(9) . 8_655 ?
N4 Ni2 N3 91.66(10) . 8_655 ?
O4 Ni2 O9 89.11(8) 8_655 . ?
O7 Ni2 O9 88.59(8) . . ?
N4 Ni2 O9 93.53(9) . . ?
N3 Ni2 O9 174.71(9) 8_655 . ?
O4 Ni2 O2 83.15(8) 8_655 3_645 ?
O7 Ni2 O2 177.75(8) . 3_645 ?
N4 Ni2 O2 91.30(9) . 3_645 ?
N3 Ni2 O2 89.65(9) 8_655 3_645 ?
O9 Ni2 O2 89.20(8) . 3_645 ?
C1 O2 Ni2 129.10(19) . 3_655 ?
C8 O3 Ni1 121.69(19) . 8_665 ?
C8 O4 Ni2 127.5(2) . 8_665 ?
C15 O6 Ni1 127.1(2) . 5_676 ?
C22 O7 Ni2 122.92(19) . . ?
C22 O8 Ni1 125.3(2) . . ?
Ni2 O9 Ni1 113.87(9) . . ?
Ni2 O9 H9A 114.2 . . ?
Ni1 O9 H9A 98.1 . . ?
Ni2 O9 H9B 97.7 . . ?
Ni1 O9 H9B 117.5 . . ?
H9A O9 H9B 116.5 . . ?
C4 N1 C3 116.9(3) . . ?
C4 N1 Ni1 119.3(2) . . ?
C3 N1 Ni1 123.5(2) . . ?
C10 N2 C11 117.4(3) . . ?
C10 N2 Ni1 118.3(2) . . ?
C11 N2 Ni1 124.3(2) . . ?
C24 N3 C25 117.4(3) . . ?
C24 N3 Ni2 118.3(2) . 8_665 ?
C25 N3 Ni2 123.8(2) . 8_665 ?
C20 N4 C19 117.1(3) . . ?
C20 N4 Ni2 121.2(2) . . ?
C19 N4 Ni2 121.7(2) . . ?
O1 C1 O2 126.1(3) . . ?
O1 C1 C2 117.5(3) . . ?
O2 C1 C2 116.4(3) . . ?
C3 C2 C6 118.2(3) . . ?
C3 C2 C1 120.5(3) . . ?
C6 C2 C1 121.3(3) . . ?
N1 C3 C2 123.3(3) . . ?
N1 C3 H3 118.3 . . ?
C2 C3 H3 118.3 . . ?
N1 C4 C5 124.1(3) . . ?
N1 C4 H4 117.9 . . ?
C5 C4 H4 117.9 . . ?
C4 C5 C6 117.4(3) . . ?
C4 C5 C7 119.8(3) . . ?
C6 C5 C7 122.8(3) . . ?
C2 C6 C5 119.8(3) . . ?
C2 C6 H6 120.1 . . ?
C5 C6 H6 120.1 . . ?
C5 C7 H7A 109.5 . . ?
C5 C7 H7B 109.5 . . ?
H7A C7 H7B 109.5 . . ?
C5 C7 H7C 109.5 . . ?
H7A C7 H7C 109.5 . . ?
H7B C7 H7C 109.5 . . ?
O4 C8 O3 127.2(3) . . ?
O4 C8 C9 115.6(3) . . ?
O3 C8 C9 117.1(3) . . ?
C13 C9 C10 118.0(3) . . ?
C13 C9 C8 123.5(3) . . ?
C10 C9 C8 118.5(3) . . ?
N2 C10 C9 123.3(3) . . ?
N2 C10 H10 118.4 . . ?
C9 C10 H10 118.4 . . ?
N2 C11 C12 123.9(3) . . ?
N2 C11 H11 118.1 . . ?
C12 C11 H11 118.1 . . ?
C11 C12 C13 117.2(3) . . ?
C11 C12 C14 121.0(3) . . ?
C13 C12 C14 121.8(3) . . ?
C9 C13 C12 120.2(3) . . ?
C9 C13 H13 119.9 . . ?
C12 C13 H13 119.9 . . ?
C12 C14 H14A 109.5 . . ?
C12 C14 H14B 109.5 . . ?
H14A C14 H14B 109.5 . . ?
C12 C14 H14C 109.5 . . ?
H14A C14 H14C 109.5 . . ?
H14B C14 H14C 109.5 . . ?
O6 C15 O5 126.4(3) . . ?
O6 C15 C16 117.3(3) . . ?
O5 C15 C16 116.3(3) . . ?
C17 C16 C20 117.6(3) . . ?
C17 C16 C15 123.5(3) . . ?
C20 C16 C15 118.8(3) . . ?
C16 C17 C18 120.7(3) . . ?
C16 C17 H17 119.6 . . ?
C18 C17 H17 119.6 . . ?
C17 C18 C19 117.0(3) . . ?
C17 C18 C21 122.4(3) . . ?
C19 C18 C21 120.5(3) . . ?
N4 C19 C18 124.0(3) . . ?
N4 C19 H19 118.0 . . ?
C18 C19 H19 118.0 . . ?
N4 C20 C16 123.5(3) . . ?
N4 C20 H20 118.3 . . ?
C16 C20 H20 118.3 . . ?
C18 C21 H21A 109.5 . . ?
C18 C21 H21B 109.5 . . ?
H21A C21 H21B 109.5 . . ?
C18 C21 H21C 109.5 . . ?
H21A C21 H21C 109.5 . . ?
H21B C21 H21C 109.5 . . ?
O8 C22 O7 126.7(3) . . ?
O8 C22 C23 116.1(3) . . ?
O7 C22 C23 117.2(3) . . ?
C27 C23 C24 118.1(3) . . ?
C27 C23 C22 123.3(3) . . ?
C24 C23 C22 118.4(3) . . ?
N3 C24 C23 123.6(3) . . ?
N3 C24 H24 118.2 . . ?
C23 C24 H24 118.2 . . ?
N3 C25 C26 123.9(3) . . ?
N3 C25 H25 118.1 . . ?
C26 C25 H25 118.1 . . ?
C25 C26 C27 117.2(3) . . ?
C25 C26 C28 120.8(3) . . ?
C27 C26 C28 122.0(3) . . ?
C23 C27 C26 119.8(3) . . ?
C23 C27 H27 120.1 . . ?
C26 C27 H27 120.1 . . ?
C26 C28 H28A 109.5 . . ?
C26 C28 H28B 109.5 . . ?
H28A C28 H28B 109.5 . . ?
C26 C28 H28C 109.5 . . ?
H28A C28 H28C 109.5 . . ?
H28B C28 H28C 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
O4 Ni2 O7 C22 -37.6(2) 8_655 . . . ?
N4 Ni2 O7 C22 144.9(2) . . . . ?
N3 Ni2 O7 C22 -123.4(2) 8_655 . . . ?
O9 Ni2 O7 C22 51.4(2) . . . . ?
O3 Ni1 O8 C22 119.9(2) 8_655 . . . ?
N2 Ni1 O8 C22 -147.1(2) . . . . ?
O6 Ni1 O8 C22 -54.9(2) 5_676 . . . ?
O9 Ni1 O8 C22 33.6(2) . . . . ?
O4 Ni2 O9 Ni1 35.91(10) 8_655 . . . ?
O7 Ni2 O9 Ni1 -60.51(10) . . . . ?
N4 Ni2 O9 Ni1 -149.67(10) . . . . ?
O2 Ni2 O9 Ni1 119.07(10) 3_645 . . . ?
O3 Ni1 O9 Ni2 -65.18(10) 8_655 . . . ?
O8 Ni1 O9 Ni2 32.07(10) . . . . ?
N1 Ni1 O9 Ni2 -155.40(10) . . . . ?
O6 Ni1 O9 Ni2 114.96(11) 5_676 . . . ?
O3 Ni1 N1 C4 -55.0(3) 8_655 . . . ?
N2 Ni1 N1 C4 -148.7(3) . . . . ?
O6 Ni1 N1 C4 119.9(2) 5_676 . . . ?
O9 Ni1 N1 C4 31.2(3) . . . . ?
O3 Ni1 N1 C3 130.5(3) 8_655 . . . ?
N2 Ni1 N1 C3 36.8(3) . . . . ?
O6 Ni1 N1 C3 -54.6(3) 5_676 . . . ?
O9 Ni1 N1 C3 -143.3(3) . . . . ?
O3 Ni1 N2 C10 151.0(2) 8_655 . . . ?
O8 Ni1 N2 C10 54.0(2) . . . . ?
N1 Ni1 N2 C10 -118.5(2) . . . . ?
O6 Ni1 N2 C10 -28.7(2) 5_676 . . . ?
O3 Ni1 N2 C11 -28.3(3) 8_655 . . . ?
O8 Ni1 N2 C11 -125.3(3) . . . . ?
N1 Ni1 N2 C11 62.2(3) . . . . ?
O6 Ni1 N2 C11 151.9(3) 5_676 . . . ?
O7 Ni2 N4 C20 -13.0(2) . . . . ?
N3 Ni2 N4 C20 -105.5(3) 8_655 . . . ?
O9 Ni2 N4 C20 75.5(2) . . . . ?
O2 Ni2 N4 C20 164.8(2) 3_645 . . . ?
O7 Ni2 N4 C19 166.5(3) . . . . ?
N3 Ni2 N4 C19 74.0(3) 8_655 . . . ?
O9 Ni2 N4 C19 -104.9(3) . . . . ?
O2 Ni2 N4 C19 -15.7(3) 3_645 . . . ?
Ni2 O2 C1 O1 15.8(5) 3_655 . . . ?
Ni2 O2 C1 C2 -164.0(2) 3_655 . . . ?
O1 C1 C2 C3 9.4(5) . . . . ?
O2 C1 C2 C3 -170.8(3) . . . . ?
O1 C1 C2 C6 -170.5(3) . . . . ?
O2 C1 C2 C6 9.3(5) . . . . ?
C4 N1 C3 C2 1.4(5) . . . . ?
Ni1 N1 C3 C2 176.0(2) . . . . ?
C6 C2 C3 N1 -4.2(5) . . . . ?
C1 C2 C3 N1 175.9(3) . . . . ?
C3 N1 C4 C5 2.9(5) . . . . ?
Ni1 N1 C4 C5 -172.0(3) . . . . ?
N1 C4 C5 C6 -4.0(6) . . . . ?
N1 C4 C5 C7 174.6(4) . . . . ?
C3 C2 C6 C5 2.8(5) . . . . ?
C1 C2 C6 C5 -177.3(3) . . . . ?
C4 C5 C6 C2 1.0(5) . . . . ?
C7 C5 C6 C2 -177.6(4) . . . . ?
Ni2 O4 C8 O3 59.8(4) 8_665 . . . ?
Ni2 O4 C8 C9 -120.3(2) 8_665 . . . ?
Ni1 O3 C8 O4 -2.1(4) 8_665 . . . ?
Ni1 O3 C8 C9 177.99(19) 8_665 . . . ?
O4 C8 C9 C13 161.9(3) . . . . ?
O3 C8 C9 C13 -18.2(5) . . . . ?
O4 C8 C9 C10 -15.6(4) . . . . ?
O3 C8 C9 C10 164.4(3) . . . . ?
C11 N2 C10 C9 -1.1(5) . . . . ?
Ni1 N2 C10 C9 179.5(2) . . . . ?
C13 C9 C10 N2 -0.3(5) . . . . ?
C8 C9 C10 N2 177.3(3) . . . . ?
C10 N2 C11 C12 1.4(5) . . . . ?
Ni1 N2 C11 C12 -179.3(3) . . . . ?
N2 C11 C12 C13 -0.3(6) . . . . ?
N2 C11 C12 C14 179.5(4) . . . . ?
C10 C9 C13 C12 1.4(5) . . . . ?
C8 C9 C13 C12 -176.1(3) . . . . ?
C11 C12 C13 C9 -1.1(6) . . . . ?
C14 C12 C13 C9 179.1(4) . . . . ?
Ni1 O6 C15 O5 -15.0(5) 5_676 . . . ?
Ni1 O6 C15 C16 163.8(2) 5_676 . . . ?
O6 C15 C16 C17 -4.3(5) . . . . ?
O5 C15 C16 C17 174.7(3) . . . . ?
O6 C15 C16 C20 179.0(3) . . . . ?
O5 C15 C16 C20 -2.1(5) . . . . ?
C20 C16 C17 C18 -2.3(5) . . . . ?
C15 C16 C17 C18 -179.1(3) . . . . ?
C16 C17 C18 C19 0.6(6) . . . . ?
C16 C17 C18 C21 179.5(4) . . . . ?
C20 N4 C19 C18 -1.9(5) . . . . ?
Ni2 N4 C19 C18 178.6(3) . . . . ?
C17 C18 C19 N4 1.6(6) . . . . ?
C21 C18 C19 N4 -177.3(4) . . . . ?
C19 N4 C20 C16 -0.1(5) . . . . ?
Ni2 N4 C20 C16 179.5(2) . . . . ?
C17 C16 C20 N4 2.1(5) . . . . ?
C15 C16 C20 N4 179.1(3) . . . . ?
Ni1 O8 C22 O7 -62.1(4) . . . . ?
Ni1 O8 C22 C23 117.0(3) . . . . ?
Ni2 O7 C22 O8 6.1(4) . . . . ?
Ni2 O7 C22 C23 -173.05(19) . . . . ?
O8 C22 C23 C27 -152.7(3) . . . . ?
O7 C22 C23 C27 26.6(4) . . . . ?
O8 C22 C23 C24 21.4(4) . . . . ?
O7 C22 C23 C24 -159.4(3) . . . . ?
C25 N3 C24 C23 1.0(5) . . . . ?
Ni2 N3 C24 C23 172.8(2) 8_665 . . . ?
C27 C23 C24 N3 -1.1(5) . . . . ?
C22 C23 C24 N3 -175.5(3) . . . . ?
C24 N3 C25 C26 0.1(5) . . . . ?
Ni2 N3 C25 C26 -171.2(3) 8_665 . . . ?
N3 C25 C26 C27 -1.0(5) . . . . ?
N3 C25 C26 C28 177.8(3) . . . . ?
C24 C23 C27 C26 0.1(5) . . . . ?
C22 C23 C27 C26 174.2(3) . . . . ?
C25 C26 C27 C23 0.8(5) . . . . ?
C28 C26 C27 C23 -177.9(3) . . . . ?

_diffrn_measured_fraction_theta_max 0.999
_diffrn_reflns_theta_full        25.03
_diffrn_measured_fraction_theta_full 0.999
_refine_diff_density_max         0.304
_refine_diff_density_min         -0.291
_refine_diff_density_rms         0.071
_database_code_depnum_ccdc_archive 'CCDC 967571'
#######################################################################
#
#                 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_967572

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C14 H14 Cl2 N2 Ni O4'
_chemical_formula_weight         403.88

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'
Ni Ni 0.3393 1.1124 '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                   13.7216(12)
_cell_length_b                   7.2942(6)
_cell_length_c                   16.2528(14)
_cell_angle_alpha                90.00
_cell_angle_beta                 92.9890(10)
_cell_angle_gamma                90.00
_cell_volume                     1624.5(2)
_cell_formula_units_Z            4
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    2992
_cell_measurement_theta_min      2.51
_cell_measurement_theta_max      30.40

_exptl_crystal_description       BLOCK
_exptl_crystal_colour            GREEN
_exptl_crystal_size_max          0.32
_exptl_crystal_size_mid          0.28
_exptl_crystal_size_min          0.22
_exptl_crystal_density_meas      NONE
_exptl_crystal_density_diffrn    1.651
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             824
_exptl_absorpt_coefficient_mu    1.543
_exptl_absorpt_correction_type   MULTI-SCAN
_exptl_absorpt_correction_T_min  0.6381
_exptl_absorpt_correction_T_max  0.7277
_exptl_absorpt_process_details   SADABS

_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  '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            3973
_diffrn_reflns_av_R_equivalents  0.0249
_diffrn_reflns_av_sigmaI/netI    0.0363
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_theta_min         2.51
_diffrn_reflns_theta_max         25.03
_reflns_number_total             1438
_reflns_number_gt                1318
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'Bruker SMART'
_computing_cell_refinement       'Bruker SMART'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'

_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)+(0.0537P)²+2.2402P] 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         1438
_refine_ls_number_parameters     106
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0376
_refine_ls_R_factor_gt           0.0351
_refine_ls_wR_factor_ref         0.0996
_refine_ls_wR_factor_gt          0.0974
_refine_ls_goodness_of_fit_ref   1.061
_refine_ls_restrained_S_all      1.061
_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
Ni1 Ni 0.5000 0.57914(5) 0.7500 0.03245(19) Uani 1 2 d S . .
Cl1 Cl 0.39487(7) 0.40239(10) 0.81408(5) 0.0600(3) Uani 1 1 d . . .
O1 O 0.55698(16) 0.7726(2) 0.82236(11) 0.0476(5) Uani 1 1 d . . .
O2 O 0.60930(18) 0.6080(2) 0.93097(14) 0.0529(6) Uani 1 1 d . . .
N1 N 0.60195(17) 1.2489(3) 0.94958(14) 0.0399(5) Uani 1 1 d . . .
H1A H 0.5892 1.3524 0.9261 0.048 Uiso 1 1 calc R . .
C1 C 0.59149(18) 0.7532(3) 0.89496(15) 0.0336(5) Uani 1 1 d . . .
C2 C 0.61047(18) 0.9292(3) 0.94214(16) 0.0309(5) Uani 1 1 d . . .
C3 C 0.5900(2) 1.0959(3) 0.90512(17) 0.0365(6) Uani 1 1 d . . .
H3 H 0.5682 1.1017 0.8500 0.044 Uiso 1 1 calc R . .
C4 C 0.63299(19) 1.2485(3) 1.02919(17) 0.0386(6) Uani 1 1 d . . .
H4 H 0.6396 1.3590 1.0575 0.046 Uiso 1 1 calc R . .
C5 C 0.65525(19) 1.0868(3) 1.06958(17) 0.0355(6) Uani 1 1 d . . .
C6 C 0.64366(18) 0.9264(3) 1.02372(17) 0.0333(6) Uani 1 1 d . . .
H6 H 0.6587 0.8145 1.0487 0.040 Uiso 1 1 calc R . .
C7 C 0.6891(2) 1.0855(4) 1.15859(19) 0.0495(7) Uani 1 1 d . . .
H7A H 0.7096 1.2066 1.1749 0.074 Uiso 1 1 calc R . .
H7B H 0.7429 1.0021 1.1666 0.074 Uiso 1 1 calc R . .
H7C H 0.6365 1.0471 1.1913 0.074 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
Ni1 O1 1.9724(18) . ?
Ni1 O1 1.9724(18) 2_656 ?
Ni1 Cl1 2.2326(8) 2_656 ?
Ni1 Cl1 2.2326(8) . ?
O1 C1 1.256(3) . ?
O2 C1 1.228(3) . ?
N1 C3 1.335(3) . ?
N1 C4 1.341(4) . ?
N1 H1A 0.8600 . ?
C1 C2 1.511(3) . ?
C2 C3 1.379(3) . ?
C2 C6 1.379(4) . ?
C3 H3 0.9300 . ?
C4 C5 1.376(4) . ?
C4 H4 0.9300 . ?
C5 C6 1.392(3) . ?
C5 C7 1.496(4) . ?
C6 H6 0.9300 . ?
C7 H7A 0.9600 . ?
C7 H7B 0.9600 . ?
C7 H7C 0.9600 . ?

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 Ni1 O1 88.62(11) . 2_656 ?
O1 Ni1 Cl1 116.47(7) . 2_656 ?
O1 Ni1 Cl1 112.38(6) 2_656 2_656 ?
O1 Ni1 Cl1 112.38(6) . . ?
O1 Ni1 Cl1 116.47(7) 2_656 . ?
Cl1 Ni1 Cl1 109.46(5) 2_656 . ?
C1 O1 Ni1 126.69(16) . . ?
C3 N1 C4 123.0(2) . . ?
C3 N1 H1A 118.5 . . ?
C4 N1 H1A 118.5 . . ?
O2 C1 O1 126.9(2) . . ?
O2 C1 C2 117.8(2) . . ?
O1 C1 C2 115.3(2) . . ?
C3 C2 C6 118.8(2) . . ?
C3 C2 C1 120.1(2) . . ?
C6 C2 C1 121.0(2) . . ?
N1 C3 C2 119.0(2) . . ?
N1 C3 H3 120.5 . . ?
C2 C3 H3 120.5 . . ?
N1 C4 C5 120.9(2) . . ?
N1 C4 H4 119.6 . . ?
C5 C4 H4 119.6 . . ?
C4 C5 C6 116.7(3) . . ?
C4 C5 C7 121.1(2) . . ?
C6 C5 C7 122.2(2) . . ?
C2 C6 C5 121.6(2) . . ?
C2 C6 H6 119.2 . . ?
C5 C6 H6 119.2 . . ?
C5 C7 H7A 109.5 . . ?
C5 C7 H7B 109.5 . . ?
H7A C7 H7B 109.5 . . ?
C5 C7 H7C 109.5 . . ?
H7A C7 H7C 109.5 . . ?
H7B C7 H7C 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
O1 Ni1 O1 C1 164.7(3) 2_656 . . . ?
Cl1 Ni1 O1 C1 -80.8(2) 2_656 . . . ?
Cl1 Ni1 O1 C1 46.6(2) . . . . ?
Ni1 O1 C1 O2 11.2(4) . . . . ?
Ni1 O1 C1 C2 -167.47(16) . . . . ?
O2 C1 C2 C3 -178.8(3) . . . . ?
O1 C1 C2 C3 0.0(4) . . . . ?
O2 C1 C2 C6 -2.1(4) . . . . ?
O1 C1 C2 C6 176.7(2) . . . . ?
C4 N1 C3 C2 -0.1(4) . . . . ?
C6 C2 C3 N1 -0.7(4) . . . . ?
C1 C2 C3 N1 176.1(2) . . . . ?
C3 N1 C4 C5 0.5(4) . . . . ?
N1 C4 C5 C6 -0.1(4) . . . . ?
N1 C4 C5 C7 -179.5(2) . . . . ?
C3 C2 C6 C5 1.1(4) . . . . ?
C1 C2 C6 C5 -175.6(2) . . . . ?
C4 C5 C6 C2 -0.7(4) . . . . ?
C7 C5 C6 C2 178.6(3) . . . . ?

_diffrn_measured_fraction_theta_max 0.999
_diffrn_reflns_theta_full        25.03
_diffrn_measured_fraction_theta_full 0.999
_refine_diff_density_max         0.312
_refine_diff_density_min         -0.541
_refine_diff_density_rms         0.072
_database_code_depnum_ccdc_archive 'CCDC 967572'
#######################################################################
#
#                 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_967573

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C14 H24 Cd2 N2 O14 S'
_chemical_formula_weight         701.21

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'
S S 0.1246 0.1234 '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                   11.761(4)
_cell_length_b                   16.623(5)
_cell_length_c                   13.751(3)
_cell_angle_alpha                90.00
_cell_angle_beta                 123.915(19)
_cell_angle_gamma                90.00
_cell_volume                     2231.0(11)
_cell_formula_units_Z            4
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    3520
_cell_measurement_theta_min      2.96
_cell_measurement_theta_max      30.10

_exptl_crystal_description       BLOCK
_exptl_crystal_colour            COLORLESS
_exptl_crystal_size_max          0.24
_exptl_crystal_size_mid          0.22
_exptl_crystal_size_min          0.20
_exptl_crystal_density_meas      NONE
_exptl_crystal_density_diffrn    2.088
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1384
_exptl_absorpt_coefficient_mu    2.073
_exptl_absorpt_correction_type   MULTI-SCAN
_exptl_absorpt_correction_T_min  0.5945
_exptl_absorpt_correction_T_max  0.6819
_exptl_absorpt_process_details   SADABS

_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  '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            11092
_diffrn_reflns_av_R_equivalents  0.0464
_diffrn_reflns_av_sigmaI/netI    0.0549
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_k_min       -19
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_theta_min         2.09
_diffrn_reflns_theta_max         25.02
_reflns_number_total             3938
_reflns_number_gt                3031
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'Bruker SMART'
_computing_cell_refinement       'Bruker SMART'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'

_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)+(0.1720P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         3938
_refine_ls_number_parameters     332
_refine_ls_number_restraints     23
_refine_ls_R_factor_all          0.0903
_refine_ls_R_factor_gt           0.0781
_refine_ls_wR_factor_ref         0.2295
_refine_ls_wR_factor_gt          0.2097
_refine_ls_goodness_of_fit_ref   1.037
_refine_ls_restrained_S_all      1.049
_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
Cd1 Cd 1.00008(4) 0.24949(3) 0.12300(4) 0.0280(3) Uani 1 1 d . . .
Cd2 Cd 0.49789(5) -0.11982(3) -0.12875(4) 0.0298(3) Uani 1 1 d . . .
S1 S 0.5093(2) -0.20281(14) -0.35074(18) 0.0408(6) Uani 1 1 d D . .
O1 O 0.7695(6) -0.1360(3) 0.0142(5) 0.0403(14) Uani 1 1 d . A .
O2 O 0.6595(6) -0.0212(3) -0.0490(5) 0.0410(14) Uani 1 1 d . A .
O3 O 1.2273(6) 0.6355(3) 0.2373(5) 0.0423(14) Uani 1 1 d . . .
O4 O 1.3376(6) 0.5206(4) 0.2887(6) 0.0489(16) Uani 1 1 d . . .
O5 O 1.1601(7) 0.2500(3) 0.3204(5) 0.0490(17) Uani 1 1 d . . .
H5A H 1.1287 0.2849 0.3447 0.073 Uiso 1 1 d R . .
H5B H 1.2397 0.2302 0.3715 0.073 Uiso 1 1 d R . .
O6 O 1.1698(6) 0.2589(3) 0.0888(5) 0.0420(15) Uani 1 1 d . . .
H6A H 1.1829 0.2253 0.0493 0.063 Uiso 1 1 d R . .
H6B H 1.2394 0.2720 0.1557 0.063 Uiso 1 1 d R . .
O7 O 0.8379(7) 0.2401(4) -0.0768(5) 0.0460(16) Uani 1 1 d . . .
H7A H 0.8643 0.2780 -0.1013 0.069 Uiso 1 1 d R . .
H7B H 0.7539 0.2396 -0.1005 0.069 Uiso 1 1 d R . .
O8 O 0.8280(6) 0.2494(3) 0.1525(6) 0.0461(16) Uani 1 1 d . . .
H8A H 0.7623 0.2699 0.0890 0.069 Uiso 1 1 d R . .
H8B H 0.8092 0.2089 0.1789 0.069 Uiso 1 1 d R . .
O9 O 0.4937(5) -0.2547(4) -0.1172(4) 0.050(3) Uani 1 1 d D A .
H9A H 0.4630 -0.2917 -0.1683 0.076 Uiso 1 1 d RD . .
H9B H 0.5104 -0.2672 -0.0504 0.076 Uiso 1 1 d RD . .
O10 O 0.4791(9) -0.1144(4) 0.0266(6) 0.069(2) Uani 1 1 d . A .
H10A H 0.4617 -0.0657 0.0325 0.104 Uiso 1 1 d R . .
H10B H 0.5255 -0.1415 0.0895 0.104 Uiso 1 1 d R . .
O11 O 0.5297(13) -0.1374(4) -0.2728(8) 0.073(7) Uani 0.717(11) 1 d PD A 1
O12 O 0.5870(8) -0.1840(5) -0.4019(7) 0.050(3) Uani 0.717(11) 1 d PD A 1
O13 O 0.5686(8) -0.2763(4) -0.2818(7) 0.053(3) Uani 0.717(11) 1 d PD A 1
O14 O 0.3705(6) -0.2133(7) -0.4382(7) 0.080(4) Uani 0.717(11) 1 d PD A 1
O11' O 0.515(3) -0.1367(10) -0.2828(18) 0.13(3) Uiso 0.283(11) 1 d PD A 2
O12' O 0.6369(12) -0.2337(15) -0.3158(19) 0.114(16) Uani 0.283(11) 1 d PD A 2
O13' O 0.4253(15) -0.2676(9) -0.3451(15) 0.052(7) Uani 0.283(11) 1 d PD A 2
O14' O 0.4286(16) -0.1809(10) -0.4752(8) 0.050(7) Uani 0.283(11) 1 d PD A 2
N1 N 1.0144(7) 0.1108(5) 0.1301(5) 0.0331(19) Uani 1 1 d . . .
N2 N 0.9850(7) 0.3881(5) 0.1157(6) 0.0351(19) Uani 1 1 d . . .
C1 C 1.1353(9) 0.0713(5) 0.1896(7) 0.0359(19) Uani 1 1 d . . .
H1 H 1.2153 0.1016 0.2288 0.043 Uiso 1 1 calc R . .
C2 C 1.1469(8) -0.0108(5) 0.1956(7) 0.0313(17) Uani 1 1 d . . .
C3 C 1.0259(8) -0.0552(5) 0.1378(6) 0.0313(18) Uani 1 1 d . . .
H3 H 1.0291 -0.1111 0.1405 0.038 Uiso 1 1 calc R . .
C4 C 0.9010(8) -0.0160(4) 0.0765(7) 0.0315(17) Uani 1 1 d . A .
C5 C 0.9003(8) 0.0674(5) 0.0740(6) 0.0295(17) Uani 1 1 d . . .
H5 H 0.8166 0.0939 0.0313 0.035 Uiso 1 1 calc R . .
C6 C 1.2851(10) -0.0516(6) 0.2642(8) 0.050(2) Uani 1 1 d . . .
H6 H 1.3540 -0.0132 0.3151 0.075 Uiso 1 1 calc R . .
H6' H 1.3058 -0.0731 0.2109 0.075 Uiso 1 1 calc R . .
H6" H 1.2833 -0.0945 0.3100 0.075 Uiso 1 1 calc R . .
C7 C 0.7678(9) -0.0602(4) 0.0102(6) 0.0317(19) Uani 1 1 d . . .
C8 C 0.8651(8) 0.4267(5) 0.0556(7) 0.0351(19) Uani 1 1 d . . .
H8 H 0.7857 0.3959 0.0150 0.042 Uiso 1 1 calc R . .
C9 C 0.8511(8) 0.5091(5) 0.0496(7) 0.0342(18) Uani 1 1 d . . .
C10 C 0.9710(8) 0.5539(5) 0.1101(7) 0.0330(18) Uani 1 1 d . . .
H10 H 0.9668 0.6098 0.1092 0.040 Uiso 1 1 calc R . .
H12 H 1.1832 0.4057 0.2138 0.040 Uiso 1 1 d R . .
C11 C 1.0975(9) 0.5152(5) 0.1722(7) 0.0366(19) Uani 1 1 d . . .
C12 C 1.0991(8) 0.4318(4) 0.1724(7) 0.0287(17) Uani 1 1 d . . .
C13 C 0.7128(10) 0.5481(6) -0.0204(8) 0.051(2) Uani 1 1 d . . .
H13A H 0.6926 0.5723 0.0317 0.077 Uiso 1 1 calc R . .
H13B H 0.6447 0.5083 -0.0677 0.077 Uiso 1 1 calc R . .
H13C H 0.7125 0.5887 -0.0702 0.077 Uiso 1 1 calc R . .
C14 C 1.2274(9) 0.5605(5) 0.2355(7) 0.0342(19) 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
Cd1 O8 2.276(7) . ?
Cd1 O5 2.282(6) . ?
Cd1 O6 2.298(6) . ?
Cd1 N2 2.308(8) . ?
Cd1 N1 2.309(8) . ?
Cd1 O7 2.316(6) . ?
Cd2 O11 2.230(7) . ?
Cd2 O9 2.251(6) . ?
Cd2 O11' 2.256(17) . ?
Cd2 O10 2.268(7) . ?
Cd2 O4 2.275(6) 4_465 ?
Cd2 O2 2.275(6) . ?
S1 O12' 1.394(8) . ?
S1 O14 1.396(6) . ?
S1 O11' 1.418(8) . ?
S1 O11 1.450(5) . ?
S1 O13 1.463(5) . ?
S1 O12 1.465(6) . ?
S1 O14' 1.466(8) . ?
S1 O13' 1.492(8) . ?
O1 C7 1.261(8) . ?
O2 C7 1.244(9) . ?
O3 C14 1.247(9) . ?
O4 C14 1.263(10) . ?
O4 Cd2 2.275(6) 4_666 ?
O5 H5A 0.8507 . ?
O5 H5B 0.8627 . ?
O6 H6A 0.8501 . ?
O6 H6B 0.8502 . ?
O7 H7A 0.8500 . ?
O7 H7B 0.8505 . ?
O8 H8A 0.8501 . ?
O8 H8B 0.8499 . ?
O9 H9A 0.8484 . ?
O9 H9B 0.8502 . ?
O10 H10A 0.8498 . ?
O10 H10B 0.8490 . ?
N1 C5 1.327(10) . ?
N1 C1 1.351(11) . ?
N2 C12 1.330(10) . ?
N2 C8 1.335(11) . ?
C1 C2 1.368(11) . ?
C1 H1 0.9300 . ?
C2 C3 1.393(11) . ?
C2 C6 1.510(11) . ?
C3 C4 1.382(11) . ?
C3 H3 0.9300 . ?
C4 C5 1.386(11) . ?
C4 C7 1.494(11) . ?
C5 H5 0.9300 . ?
C6 H6 0.9600 . ?
C6 H6' 0.9600 . ?
C6 H6" 0.9600 . ?
C8 C9 1.376(11) . ?
C8 H8 0.9300 . ?
C9 C10 1.388(11) . ?
C9 C13 1.498(11) . ?
C10 C11 1.393(12) . ?
C10 H10 0.9300 . ?
C11 C12 1.387(11) . ?
C11 C14 1.474(12) . ?
C12 H12 0.9295 . ?
C13 H13A 0.9600 . ?
C13 H13B 0.9600 . ?
C13 H13C 0.9600 . ?

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
O8 Cd1 O5 90.8(2) . . ?
O8 Cd1 O6 175.92(19) . . ?
O5 Cd1 O6 90.5(2) . . ?
O8 Cd1 N2 87.3(2) . . ?
O5 Cd1 N2 92.3(2) . . ?
O6 Cd1 N2 88.7(2) . . ?
O8 Cd1 N1 92.5(2) . . ?
O5 Cd1 N1 87.8(2) . . ?
O6 Cd1 N1 91.5(2) . . ?
N2 Cd1 N1 179.8(4) . . ?
O8 Cd1 O7 89.2(2) . . ?
O5 Cd1 O7 176.4(2) . . ?
O6 Cd1 O7 89.8(2) . . ?
N2 Cd1 O7 91.3(2) . . ?
N1 Cd1 O7 88.6(2) . . ?
O11 Cd2 O9 87.3(2) . . ?
O11 Cd2 O11' 3.7(9) . . ?
O9 Cd2 O11' 87.7(5) . . ?
O11 Cd2 O10 173.7(3) . . ?
O9 Cd2 O10 87.4(2) . . ?
O11' Cd2 O10 175.1(5) . . ?
O11 Cd2 O4 98.9(3) . 4_465 ?
O9 Cd2 O4 135.5(2) . 4_465 ?
O11' Cd2 O4 96.1(6) . 4_465 ?
O10 Cd2 O4 87.3(3) . 4_465 ?
O11 Cd2 O2 90.8(3) . . ?
O9 Cd2 O2 136.8(2) . . ?
O11' Cd2 O2 93.1(6) . . ?
O10 Cd2 O2 90.7(3) . . ?
O4 Cd2 O2 87.4(3) 4_465 . ?
O12' S1 O14 140.1(12) . . ?
O12' S1 O11' 114.2(8) . . ?
O14 S1 O11' 105.6(12) . . ?
O12' S1 O11 108.6(13) . . ?
O14 S1 O11 111.2(5) . . ?
O12' S1 O13 55.7(9) . . ?
O14 S1 O13 111.1(5) . . ?
O11' S1 O13 112.9(10) . . ?
O11 S1 O13 109.0(5) . . ?
O12' S1 O12 53.4(9) . . ?
O14 S1 O12 110.8(5) . . ?
O11' S1 O12 109.7(11) . . ?
O11 S1 O12 107.8(5) . . ?
O13 S1 O12 106.8(4) . . ?
O12' S1 O14' 111.4(8) . . ?
O14 S1 O14' 48.8(7) . . ?
O11' S1 O14' 109.8(8) . . ?
O11 S1 O14' 114.2(8) . . ?
O13 S1 O14' 136.7(8) . . ?
O12 S1 O14' 63.7(7) . . ?
O12' S1 O13' 109.4(8) . . ?
O14 S1 O13' 57.7(7) . . ?
O11' S1 O13' 108.4(8) . . ?
O11 S1 O13' 110.2(9) . . ?
O13 S1 O13' 56.9(7) . . ?
O12 S1 O13' 141.9(8) . . ?
O14' S1 O13' 102.9(6) . . ?
C7 O2 Cd2 102.4(5) . . ?
C14 O4 Cd2 101.9(5) . 4_666 ?
Cd1 O5 H5A 102.7 . . ?
Cd1 O5 H5B 140.1 . . ?
H5A O5 H5B 116.9 . . ?
Cd1 O6 H6A 124.9 . . ?
Cd1 O6 H6B 102.6 . . ?
H6A O6 H6B 116.9 . . ?
Cd1 O7 H7A 100.3 . . ?
Cd1 O7 H7B 117.9 . . ?
H7A O7 H7B 117.3 . . ?
Cd1 O8 H8A 101.9 . . ?
Cd1 O8 H8B 123.0 . . ?
H8A O8 H8B 116.9 . . ?
Cd2 O9 H9A 132.8 . . ?
Cd2 O9 H9B 108.5 . . ?
H9A O9 H9B 117.0 . . ?
Cd2 O10 H10A 106.4 . . ?
Cd2 O10 H10B 126.4 . . ?
H10A O10 H10B 117.3 . . ?
S1 O11 Cd2 135.6(5) . . ?
S1 O11' Cd2 135.9(14) . . ?
C5 N1 C1 117.9(8) . . ?
C5 N1 Cd1 119.5(6) . . ?
C1 N1 Cd1 122.6(5) . . ?
C12 N2 C8 118.1(8) . . ?
C12 N2 Cd1 119.5(6) . . ?
C8 N2 Cd1 122.4(6) . . ?
N1 C1 C2 123.9(8) . . ?
N1 C1 H1 118.1 . . ?
C2 C1 H1 118.1 . . ?
C1 C2 C3 117.3(7) . . ?
C1 C2 C6 121.5(8) . . ?
C3 C2 C6 121.3(8) . . ?
C4 C3 C2 119.8(8) . . ?
C4 C3 H3 120.1 . . ?
C2 C3 H3 120.1 . . ?
C3 C4 C5 118.4(7) . . ?
C3 C4 C7 122.4(7) . . ?
C5 C4 C7 119.1(7) . . ?
N1 C5 C4 122.7(8) . . ?
N1 C5 H5 118.7 . . ?
C4 C5 H5 118.7 . . ?
C2 C6 H6 109.5 . . ?
C2 C6 H6' 109.5 . . ?
H6 C6 H6' 109.5 . . ?
C2 C6 H6" 109.5 . . ?
H6 C6 H6" 109.5 . . ?
H6' C6 H6" 109.5 . . ?
O2 C7 O1 122.4(7) . . ?
O2 C7 C4 119.0(7) . . ?
O1 C7 C4 118.6(7) . . ?
N2 C8 C9 124.5(8) . . ?
N2 C8 H8 117.8 . . ?
C9 C8 H8 117.8 . . ?
C8 C9 C10 116.8(8) . . ?
C8 C9 C13 121.3(8) . . ?
C10 C9 C13 121.9(8) . . ?
C9 C10 C11 120.0(8) . . ?
C9 C10 H10 120.0 . . ?
C11 C10 H10 120.0 . . ?
C12 C11 C10 118.1(8) . . ?
C12 C11 C14 120.1(8) . . ?
C10 C11 C14 121.8(7) . . ?
N2 C12 C11 122.5(8) . . ?
N2 C12 H12 119.0 . . ?
C11 C12 H12 118.5 . . ?
C9 C13 H13A 109.5 . . ?
C9 C13 H13B 109.5 . . ?
H13A C13 H13B 109.5 . . ?
C9 C13 H13C 109.5 . . ?
H13A C13 H13C 109.5 . . ?
H13B C13 H13C 109.5 . . ?
O3 C14 O4 121.7(8) . . ?
O3 C14 C11 120.6(8) . . ?
O4 C14 C11 117.7(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
O11 Cd2 O2 C7 -83.7(6) . . . . ?
O9 Cd2 O2 C7 3.3(6) . . . . ?
O11' Cd2 O2 C7 -86.6(8) . . . . ?
O10 Cd2 O2 C7 90.2(5) . . . . ?
O4 Cd2 O2 C7 177.5(5) 4_465 . . . ?
O12' S1 O11 Cd2 -107.2(14) . . . . ?
O14 S1 O11 Cd2 74.7(11) . . . . ?
O11' S1 O11 Cd2 86(11) . . . . ?
O13 S1 O11 Cd2 -48.1(12) . . . . ?
O12 S1 O11 Cd2 -163.6(9) . . . . ?
O14' S1 O11 Cd2 127.9(11) . . . . ?
O13' S1 O11 Cd2 12.6(13) . . . . ?
O9 Cd2 O11 S1 18.6(10) . . . . ?
O11' Cd2 O11 S1 -77(8) . . . . ?
O4 Cd2 O11 S1 -117.1(10) 4_465 . . . ?
O2 Cd2 O11 S1 155.4(10) . . . . ?
O12' S1 O11' Cd2 -96(2) . . . . ?
O14 S1 O11' Cd2 86(2) . . . . ?
O11 S1 O11' Cd2 -83(11) . . . . ?
O13 S1 O11' Cd2 -35(3) . . . . ?
O12 S1 O11' Cd2 -154.2(19) . . . . ?
O14' S1 O11' Cd2 138(2) . . . . ?
O13' S1 O11' Cd2 26(2) . . . . ?
O11 Cd2 O11' S1 91(9) . . . . ?
O9 Cd2 O11' S1 7(2) . . . . ?
O4 Cd2 O11' S1 -129(2) 4_465 . . . ?
O2 Cd2 O11' S1 143(2) . . . . ?
O8 Cd1 N1 C5 43.7(6) . . . . ?
O5 Cd1 N1 C5 134.4(6) . . . . ?
O6 Cd1 N1 C5 -135.2(6) . . . . ?
O7 Cd1 N1 C5 -45.4(6) . . . . ?
O8 Cd1 N1 C1 -136.4(6) . . . . ?
O5 Cd1 N1 C1 -45.7(6) . . . . ?
O6 Cd1 N1 C1 44.8(6) . . . . ?
O7 Cd1 N1 C1 134.5(6) . . . . ?
O8 Cd1 N2 C12 136.0(6) . . . . ?
O5 Cd1 N2 C12 45.3(6) . . . . ?
O6 Cd1 N2 C12 -45.2(6) . . . . ?
O7 Cd1 N2 C12 -134.9(6) . . . . ?
O8 Cd1 N2 C8 -44.5(6) . . . . ?
O5 Cd1 N2 C8 -135.1(6) . . . . ?
O6 Cd1 N2 C8 134.4(6) . . . . ?
O7 Cd1 N2 C8 44.6(7) . . . . ?
C5 N1 C1 C2 -0.2(12) . . . . ?
Cd1 N1 C1 C2 179.9(6) . . . . ?
N1 C1 C2 C3 -1.0(13) . . . . ?
N1 C1 C2 C6 -179.6(8) . . . . ?
C1 C2 C3 C4 0.8(11) . . . . ?
C6 C2 C3 C4 179.5(8) . . . . ?
C2 C3 C4 C5 0.3(11) . . . . ?
C2 C3 C4 C7 178.3(7) . . . . ?
C1 N1 C5 C4 1.5(11) . . . . ?
Cd1 N1 C5 C4 -178.6(6) . . . . ?
C3 C4 C5 N1 -1.6(12) . . . . ?
C7 C4 C5 N1 -179.6(7) . . . . ?
Cd2 O2 C7 O1 0.8(8) . . . . ?
Cd2 O2 C7 C4 179.1(6) . . . . ?
C3 C4 C7 O2 -175.6(7) . . . . ?
C5 C4 C7 O2 2.4(11) . . . . ?
C3 C4 C7 O1 2.8(12) . . . . ?
C5 C4 C7 O1 -179.2(7) . . . . ?
C12 N2 C8 C9 -1.1(12) . . . . ?
Cd1 N2 C8 C9 179.4(6) . . . . ?
N2 C8 C9 C10 0.5(13) . . . . ?
N2 C8 C9 C13 179.6(8) . . . . ?
C8 C9 C10 C11 0.4(12) . . . . ?
C13 C9 C10 C11 -178.7(8) . . . . ?
C9 C10 C11 C12 -0.7(12) . . . . ?
C9 C10 C11 C14 178.7(8) . . . . ?
C8 N2 C12 C11 0.7(12) . . . . ?
Cd1 N2 C12 C11 -179.7(6) . . . . ?
C10 C11 C12 N2 0.2(12) . . . . ?
C14 C11 C12 N2 -179.3(7) . . . . ?
Cd2 O4 C14 O3 0.5(9) 4_666 . . . ?
Cd2 O4 C14 C11 -178.6(6) 4_666 . . . ?
C12 C11 C14 O3 -179.0(8) . . . . ?
C10 C11 C14 O3 1.5(12) . . . . ?
C12 C11 C14 O4 0.1(12) . . . . ?
C10 C11 C14 O4 -179.3(8) . . . . ?

_diffrn_measured_fraction_theta_max 0.998
_diffrn_reflns_theta_full        25.02
_diffrn_measured_fraction_theta_full 0.998
_refine_diff_density_max         1.264
_refine_diff_density_min         -1.532
_refine_diff_density_rms         0.312
_database_code_depnum_ccdc_archive 'CCDC 967573'
#######################################################################
#
#                 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_4

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C14 H14 Cd N2 O5'
_chemical_formula_weight         402.67

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           Triclinic
_symmetry_space_group_name_H-M   P-1

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

_cell_length_a                   7.5497(9)
_cell_length_b                   8.1071(10)
_cell_length_c                   12.7747(16)
_cell_angle_alpha                108.251(2)
_cell_angle_beta                 92.214(2)
_cell_angle_gamma                100.358(2)
_cell_volume                     726.67(15)
_cell_formula_units_Z            2
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    2189
_cell_measurement_theta_min      2.70
_cell_measurement_theta_max      29.44

_exptl_crystal_description       BLOCK
_exptl_crystal_colour            COLORLESS
_exptl_crystal_size_max          0.28
_exptl_crystal_size_mid          0.24
_exptl_crystal_size_min          0.20
_exptl_crystal_density_meas      NONE
_exptl_crystal_density_diffrn    1.840
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             400
_exptl_absorpt_coefficient_mu    1.528
_exptl_absorpt_correction_type   MULTI-SCAN
_exptl_absorpt_correction_T_min  0.6743
_exptl_absorpt_correction_T_max  0.7498
_exptl_absorpt_process_details   SADABS

_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  '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            3730
_diffrn_reflns_av_R_equivalents  0.0135
_diffrn_reflns_av_sigmaI/netI    0.0270
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_theta_min         1.69
_diffrn_reflns_theta_max         25.02
_reflns_number_total             2547
_reflns_number_gt                2319
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'Bruker SMART'
_computing_cell_refinement       'Bruker SMART'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'

_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)+(0.0282P)²+0.3523P] 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         2547
_refine_ls_number_parameters     201
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0277
_refine_ls_R_factor_gt           0.0235
_refine_ls_wR_factor_ref         0.0563
_refine_ls_wR_factor_gt          0.0541
_refine_ls_goodness_of_fit_ref   1.047
_refine_ls_restrained_S_all      1.047
_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 1.05626(3) 0.05780(3) 0.233294(17) 0.02812(9) Uani 1 1 d . . .
O1 O 0.8720(3) -0.0480(4) 0.34065(18) 0.0485(6) Uani 1 1 d . . .
O2 O 0.6026(3) -0.1736(4) 0.24521(18) 0.0505(7) Uani 1 1 d . . .
O3 O 1.0686(3) 0.3589(3) 0.24971(18) 0.0398(5) Uani 1 1 d . . .
O4 O 1.1805(3) 0.1995(3) 0.10411(18) 0.0358(5) Uani 1 1 d . . .
O5 O 0.7903(3) -0.0228(3) 0.11606(17) 0.0399(5) Uani 1 1 d . . .
H5A H 0.7164 -0.0741 0.1501 0.060 Uiso 1 1 d R . .
H5B H 0.7920 -0.0772 0.0475 0.060 Uiso 1 1 d R . .
N1 N 0.7156(3) -0.1494(3) 0.6190(2) 0.0343(6) Uani 1 1 d . . .
N2 N 1.1540(3) 0.7997(3) 0.1447(2) 0.0303(6) Uani 1 1 d . . .
C1 C 0.6438(4) -0.1700(4) 0.4307(2) 0.0318(7) Uani 1 1 d . . .
C2 C 0.7620(4) -0.1191(4) 0.5260(2) 0.0339(7) Uani 1 1 d . . .
H2 H 0.8797 -0.0608 0.5251 0.041 Uiso 1 1 calc R . .
C3 C 0.5457(4) -0.2328(4) 0.6190(3) 0.0368(7) Uani 1 1 d . . .
H3 H 0.5118 -0.2530 0.6839 0.044 Uiso 1 1 calc R . .
C4 C 0.4178(4) -0.2905(4) 0.5283(3) 0.0354(7) Uani 1 1 d . . .
C5 C 0.4703(4) -0.2571(4) 0.4322(3) 0.0351(7) Uani 1 1 d . . .
H5 H 0.3882 -0.2935 0.3693 0.042 Uiso 1 1 calc R . .
C6 C 0.2275(5) -0.3825(5) 0.5343(3) 0.0547(10) Uani 1 1 d . . .
H6A H 0.2233 -0.4146 0.6005 0.082 Uiso 1 1 calc R . .
H6B H 0.1925 -0.4874 0.4708 0.082 Uiso 1 1 calc R . .
H6C H 0.1459 -0.3040 0.5354 0.082 Uiso 1 1 calc R . .
C7 C 0.7088(4) -0.1285(4) 0.3297(3) 0.0334(7) Uani 1 1 d . . .
C8 C 1.1738(4) 0.4988(4) 0.1196(2) 0.0275(6) Uani 1 1 d . . .
C9 C 1.1255(4) 0.6570(4) 0.1782(2) 0.0299(7) Uani 1 1 d . . .
H9 H 1.0713 0.6642 0.2432 0.036 Uiso 1 1 calc R . .
C10 C 1.2327(4) 0.7870(4) 0.0507(3) 0.0324(7) Uani 1 1 d . . .
H10 H 1.2560 0.8873 0.0288 0.039 Uiso 1 1 calc R . .
C11 C 1.2811(4) 0.6351(4) -0.0153(2) 0.0302(7) Uani 1 1 d . . .
C12 C 1.2523(4) 0.4898(4) 0.0219(2) 0.0297(6) Uani 1 1 d . . .
H12 H 1.2860 0.3854 -0.0190 0.036 Uiso 1 1 calc R . .
C13 C 1.1383(4) 0.3426(4) 0.1610(2) 0.0285(6) Uani 1 1 d . . .
C14 C 1.3578(5) 0.6286(5) -0.1228(3) 0.0407(8) Uani 1 1 d . . .
H14A H 1.3993 0.5195 -0.1524 0.061 Uiso 1 1 calc R . .
H14B H 1.4575 0.7268 -0.1103 0.061 Uiso 1 1 calc R . .
H14C H 1.2659 0.6352 -0.1745 0.061 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 O1 2.237(2) . ?
Cd1 N2 2.311(2) 1_545 ?
Cd1 O5 2.320(2) . ?
Cd1 N1 2.343(3) 2_756 ?
Cd1 O3 2.368(2) . ?
Cd1 O4 2.417(2) . ?
Cd1 C13 2.727(3) . ?
O1 C7 1.266(4) . ?
O2 C7 1.234(4) . ?
O3 C13 1.247(4) . ?
O4 C13 1.264(4) . ?
O5 H5A 0.8500 . ?
O5 H5B 0.8499 . ?
N1 C2 1.333(4) . ?
N1 C3 1.338(4) . ?
N1 Cd1 2.343(3) 2_756 ?
N2 C9 1.340(4) . ?
N2 C10 1.344(4) . ?
N2 Cd1 2.311(2) 1_565 ?
C1 C5 1.376(4) . ?
C1 C2 1.386(4) . ?
C1 C7 1.510(4) . ?
C2 H2 0.9300 . ?
C3 C4 1.381(5) . ?
C3 H3 0.9300 . ?
C4 C5 1.394(4) . ?
C4 C6 1.511(4) . ?
C5 H5 0.9300 . ?
C6 H6A 0.9600 . ?
C6 H6B 0.9600 . ?
C6 H6C 0.9600 . ?
C8 C9 1.388(4) . ?
C8 C12 1.389(4) . ?
C8 C13 1.504(4) . ?
C9 H9 0.9300 . ?
C10 C11 1.377(4) . ?
C10 H10 0.9300 . ?
C11 C12 1.388(4) . ?
C11 C14 1.500(4) . ?
C12 H12 0.9300 . ?
C14 H14A 0.9600 . ?
C14 H14B 0.9600 . ?
C14 H14C 0.9600 . ?

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 Cd1 N2 97.76(9) . 1_545 ?
O1 Cd1 O5 81.92(8) . . ?
N2 Cd1 O5 93.71(8) 1_545 . ?
O1 Cd1 N1 87.76(8) . 2_756 ?
N2 Cd1 N1 93.69(9) 1_545 2_756 ?
O5 Cd1 N1 168.02(8) . 2_756 ?
O1 Cd1 O3 115.68(9) . . ?
N2 Cd1 O3 146.53(8) 1_545 . ?
O5 Cd1 O3 89.94(8) . . ?
N1 Cd1 O3 89.08(8) 2_756 . ?
O1 Cd1 O4 163.90(8) . . ?
N2 Cd1 O4 92.37(8) 1_545 . ?
O5 Cd1 O4 84.99(8) . . ?
N1 Cd1 O4 104.10(8) 2_756 . ?
O3 Cd1 O4 54.80(7) . . ?
O1 Cd1 C13 141.25(10) . . ?
N2 Cd1 C13 119.86(9) 1_545 . ?
O5 Cd1 C13 86.42(8) . . ?
N1 Cd1 C13 98.02(9) 2_756 . ?
O3 Cd1 C13 27.19(8) . . ?
O4 Cd1 C13 27.63(8) . . ?
C7 O1 Cd1 135.7(2) . . ?
C13 O3 Cd1 92.62(18) . . ?
C13 O4 Cd1 89.93(17) . . ?
Cd1 O5 H5A 102.3 . . ?
Cd1 O5 H5B 119.3 . . ?
H5A O5 H5B 116.4 . . ?
C2 N1 C3 117.6(3) . . ?
C2 N1 Cd1 116.5(2) . 2_756 ?
C3 N1 Cd1 125.9(2) . 2_756 ?
C9 N2 C10 118.0(3) . . ?
C9 N2 Cd1 123.3(2) . 1_565 ?
C10 N2 Cd1 118.59(18) . 1_565 ?
C5 C1 C2 118.1(3) . . ?
C5 C1 C7 122.6(3) . . ?
C2 C1 C7 119.3(3) . . ?
N1 C2 C1 123.3(3) . . ?
N1 C2 H2 118.4 . . ?
C1 C2 H2 118.4 . . ?
N1 C3 C4 123.8(3) . . ?
N1 C3 H3 118.1 . . ?
C4 C3 H3 118.1 . . ?
C3 C4 C5 117.3(3) . . ?
C3 C4 C6 121.1(3) . . ?
C5 C4 C6 121.6(3) . . ?
C1 C5 C4 119.9(3) . . ?
C1 C5 H5 120.0 . . ?
C4 C5 H5 120.0 . . ?
C4 C6 H6A 109.5 . . ?
C4 C6 H6B 109.5 . . ?
H6A C6 H6B 109.5 . . ?
C4 C6 H6C 109.5 . . ?
H6A C6 H6C 109.5 . . ?
H6B C6 H6C 109.5 . . ?
O2 C7 O1 125.7(3) . . ?
O2 C7 C1 119.0(3) . . ?
O1 C7 C1 115.4(3) . . ?
C9 C8 C12 117.9(3) . . ?
C9 C8 C13 120.2(3) . . ?
C12 C8 C13 121.9(3) . . ?
N2 C9 C8 122.5(3) . . ?
N2 C9 H9 118.7 . . ?
C8 C9 H9 118.7 . . ?
N2 C10 C11 124.2(3) . . ?
N2 C10 H10 117.9 . . ?
C11 C10 H10 117.9 . . ?
C10 C11 C12 116.7(3) . . ?
C10 C11 C14 120.9(3) . . ?
C12 C11 C14 122.4(3) . . ?
C11 C12 C8 120.7(3) . . ?
C11 C12 H12 119.7 . . ?
C8 C12 H12 119.7 . . ?
O3 C13 O4 122.6(3) . . ?
O3 C13 C8 119.0(3) . . ?
O4 C13 C8 118.4(3) . . ?
O3 C13 Cd1 60.19(15) . . ?
O4 C13 Cd1 62.45(15) . . ?
C8 C13 Cd1 177.2(2) . . ?
C11 C14 H14A 109.5 . . ?
C11 C14 H14B 109.5 . . ?
H14A C14 H14B 109.5 . . ?
C11 C14 H14C 109.5 . . ?
H14A C14 H14C 109.5 . . ?
H14B C14 H14C 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
N2 Cd1 O1 C7 -85.8(3) 1_545 . . . ?
O5 Cd1 O1 C7 6.8(3) . . . . ?
N1 Cd1 O1 C7 -179.3(3) 2_756 . . . ?
O3 Cd1 O1 C7 92.9(3) . . . . ?
O4 Cd1 O1 C7 42.7(5) . . . . ?
C13 Cd1 O1 C7 80.7(4) . . . . ?
O1 Cd1 O3 C13 -163.26(17) . . . . ?
N2 Cd1 O3 C13 14.4(3) 1_545 . . . ?
O5 Cd1 O3 C13 -82.26(19) . . . . ?
N1 Cd1 O3 C13 109.68(19) 2_756 . . . ?
O4 Cd1 O3 C13 1.64(17) . . . . ?
O1 Cd1 O4 C13 56.3(4) . . . . ?
N2 Cd1 O4 C13 -174.63(18) 1_545 . . . ?
O5 Cd1 O4 C13 91.85(18) . . . . ?
N1 Cd1 O4 C13 -80.22(18) 2_756 . . . ?
O3 Cd1 O4 C13 -1.62(17) . . . . ?
C3 N1 C2 C1 -0.3(5) . . . . ?
Cd1 N1 C2 C1 178.1(2) 2_756 . . . ?
C5 C1 C2 N1 -0.4(5) . . . . ?
C7 C1 C2 N1 179.6(3) . . . . ?
C2 N1 C3 C4 0.9(5) . . . . ?
Cd1 N1 C3 C4 -177.3(2) 2_756 . . . ?
N1 C3 C4 C5 -0.8(5) . . . . ?
N1 C3 C4 C6 -179.5(3) . . . . ?
C2 C1 C5 C4 0.4(5) . . . . ?
C7 C1 C5 C4 -179.5(3) . . . . ?
C3 C4 C5 C1 0.1(5) . . . . ?
C6 C4 C5 C1 178.8(3) . . . . ?
Cd1 O1 C7 O2 1.0(6) . . . . ?
Cd1 O1 C7 C1 -178.9(2) . . . . ?
C5 C1 C7 O2 0.3(5) . . . . ?
C2 C1 C7 O2 -179.7(3) . . . . ?
C5 C1 C7 O1 -179.9(3) . . . . ?
C2 C1 C7 O1 0.1(4) . . . . ?
C10 N2 C9 C8 -0.1(4) . . . . ?
Cd1 N2 C9 C8 175.3(2) 1_565 . . . ?
C12 C8 C9 N2 -0.9(4) . . . . ?
C13 C8 C9 N2 -179.9(3) . . . . ?
C9 N2 C10 C11 2.0(5) . . . . ?
Cd1 N2 C10 C11 -173.6(2) 1_565 . . . ?
N2 C10 C11 C12 -2.8(5) . . . . ?
N2 C10 C11 C14 176.1(3) . . . . ?
C10 C11 C12 C8 1.7(4) . . . . ?
C14 C11 C12 C8 -177.2(3) . . . . ?
C9 C8 C12 C11 0.0(4) . . . . ?
C13 C8 C12 C11 179.0(3) . . . . ?
Cd1 O3 C13 O4 -3.0(3) . . . . ?
Cd1 O3 C13 C8 176.9(2) . . . . ?
Cd1 O4 C13 O3 3.0(3) . . . . ?
Cd1 O4 C13 C8 -177.0(2) . . . . ?
C9 C8 C13 O3 -1.5(4) . . . . ?
C12 C8 C13 O3 179.5(3) . . . . ?
C9 C8 C13 O4 178.5(3) . . . . ?
C12 C8 C13 O4 -0.6(4) . . . . ?
O1 Cd1 C13 O3 24.5(2) . . . . ?
N2 Cd1 C13 O3 -170.92(17) 1_545 . . . ?
O5 Cd1 C13 O3 96.86(19) . . . . ?
N1 Cd1 C13 O3 -71.95(19) 2_756 . . . ?
O4 Cd1 C13 O3 -177.1(3) . . . . ?
O1 Cd1 C13 O4 -158.39(16) . . . . ?
N2 Cd1 C13 O4 6.2(2) 1_545 . . . ?
O5 Cd1 C13 O4 -86.03(18) . . . . ?
N1 Cd1 C13 O4 105.16(18) 2_756 . . . ?
O3 Cd1 C13 O4 177.1(3) . . . . ?


_diffrn_measured_fraction_theta_max 0.994
_diffrn_reflns_theta_full        25.02
_diffrn_measured_fraction_theta_full 0.994
_refine_diff_density_max         0.383
_refine_diff_density_min         -0.320
_refine_diff_density_rms         0.071
_database_code_depnum_ccdc_archive 'CCDC 967574'
#######################################################################
#
#                 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_967575


_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C14 H18 Cu N2 O7'
_chemical_formula_weight         389.84

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'
Cu Cu 0.3201 1.2651 '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                   26.521(2)
_cell_length_b                   8.8621(7)
_cell_length_c                   16.7474(13)
_cell_angle_alpha                90.00
_cell_angle_beta                 117.7800(10)
_cell_angle_gamma                90.00
_cell_volume                     3482.4(5)
_cell_formula_units_Z            8
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    3242
_cell_measurement_theta_min      2.47
_cell_measurement_theta_max      27.12

_exptl_crystal_description       BLOCK
_exptl_crystal_colour            BLUE
_exptl_crystal_size_max          0.28
_exptl_crystal_size_mid          0.22
_exptl_crystal_size_min          0.20
_exptl_crystal_density_meas      NONE
_exptl_crystal_density_diffrn    1.487
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1608
_exptl_absorpt_coefficient_mu    1.291
_exptl_absorpt_correction_type   MULTI-SCAN
_exptl_absorpt_correction_T_min  0.7139
_exptl_absorpt_correction_T_max  0.7823
_exptl_absorpt_process_details   SADABS

_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  '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            8700
_diffrn_reflns_av_R_equivalents  0.0225
_diffrn_reflns_av_sigmaI/netI    0.0262
_diffrn_reflns_limit_h_min       -22
_diffrn_reflns_limit_h_max       31
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_theta_min         1.74
_diffrn_reflns_theta_max         25.03
_reflns_number_total             3086
_reflns_number_gt                2575
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'Bruker SMART'
_computing_cell_refinement       'Bruker SMART'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'

_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)+(0.0450P)²+8.3518P] 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         3086
_refine_ls_number_parameters     222
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0443
_refine_ls_R_factor_gt           0.0346
_refine_ls_wR_factor_ref         0.0955
_refine_ls_wR_factor_gt          0.0894
_refine_ls_goodness_of_fit_ref   1.042
_refine_ls_restrained_S_all      1.042
_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
Cu1 Cu 1.0000 1.0000 0.5000 0.02830(16) Uani 1 2 d S . .
Cu2 Cu 1.2500 0.7500 0.5000 0.02411(15) Uani 1 2 d S . .
O1 O 0.92045(8) 0.9921(2) 0.40504(13) 0.0341(5) Uani 1 1 d . . .
O2 O 0.92418(10) 1.0396(3) 0.27727(16) 0.0529(7) Uani 1 1 d . . .
O3 O 1.17139(8) 0.7166(2) 0.47788(14) 0.0309(5) Uani 1 1 d . . .
O4 O 1.15000(11) 0.4830(3) 0.4244(2) 0.0654(9) Uani 1 1 d . . .
O5 O 1.02931(11) 1.1393(3) 0.40617(18) 0.0578(7) Uani 1 1 d . . .
H5A H 1.0436 1.1179 0.3719 0.087 Uiso 1 1 d R . .
H5B H 0.9931 1.1289 0.3821 0.087 Uiso 1 1 d R . .
O6 O 1.26694(11) 0.4922(3) 0.47557(17) 0.0472(6) Uani 1 1 d . . .
H6A H 1.2341 0.4631 0.4660 0.071 Uiso 1 1 d R . .
H6B H 1.2951 0.4411 0.5134 0.071 Uiso 1 1 d R . .
O7 O 0.13345(11) 0.1709(3) 0.39815(19) 0.0594(7) Uani 1 1 d . . .
H7A H 0.1429 0.1988 0.4518 0.089 Uiso 1 1 d R . .
H7B H 0.1099 0.2283 0.3556 0.089 Uiso 1 1 d R . .
N1 N 0.77797(10) 0.7895(3) 0.13297(15) 0.0289(6) Uani 1 1 d . . .
N2 N 1.01534(10) 0.7996(3) 0.45598(16) 0.0283(5) Uani 1 1 d . . .
C1 C 0.90172(13) 0.9853(3) 0.3207(2) 0.0314(7) Uani 1 1 d . . .
C2 C 0.84631(12) 0.9006(3) 0.27080(19) 0.0284(6) Uani 1 1 d . . .
C3 C 0.81344(14) 0.8610(4) 0.3113(2) 0.0382(8) Uani 1 1 d . . .
H3 H 0.8258 0.8841 0.3717 0.046 Uiso 1 1 calc R . .
C4 C 0.76188(16) 0.7868(4) 0.2622(2) 0.0460(9) Uani 1 1 d . . .
C5 C 0.74657(14) 0.7531(4) 0.1734(2) 0.0387(8) Uani 1 1 d . . .
H5 H 0.7124 0.7022 0.1398 0.046 Uiso 1 1 calc R . .
C6 C 0.82739(12) 0.8622(3) 0.18144(19) 0.0281(6) Uani 1 1 d . . .
H6 H 0.8497 0.8876 0.1539 0.034 Uiso 1 1 calc R . .
C7 C 0.7234(2) 0.7474(6) 0.3028(3) 0.0884(19) Uani 1 1 d . . .
H7A' H 0.7408 0.6695 0.3471 0.133 Uiso 1 1 calc R . .
H7B' H 0.6874 0.7123 0.2561 0.133 Uiso 1 1 calc R . .
H7C' H 0.7174 0.8353 0.3308 0.133 Uiso 1 1 calc R . .
C8 C 1.13786(13) 0.6061(4) 0.4455(2) 0.0329(7) Uani 1 1 d . . .
C9 C 1.07863(12) 0.6348(3) 0.43222(19) 0.0292(6) Uani 1 1 d . . .
C10 C 1.03518(14) 0.5295(3) 0.3924(2) 0.0367(7) Uani 1 1 d . . .
H10 H 1.0420 0.4388 0.3712 0.044 Uiso 1 1 calc R . .
C11 C 0.98167(13) 0.5591(3) 0.3841(2) 0.0344(7) Uani 1 1 d . . .
C12 C 0.97452(12) 0.6934(3) 0.4193(2) 0.0321(7) Uani 1 1 d . . .
H12 H 0.9395 0.7116 0.4177 0.039 Uiso 1 1 calc R . .
C13 C 1.06641(12) 0.7693(3) 0.46138(19) 0.0281(6) Uani 1 1 d . . .
H13 H 1.0949 0.8421 0.4858 0.034 Uiso 1 1 calc R . .
C14 C 0.93245(15) 0.4499(4) 0.3399(3) 0.0531(10) Uani 1 1 d . . .
H14A H 0.9036 0.4749 0.3569 0.080 Uiso 1 1 calc R . .
H14B H 0.9457 0.3490 0.3592 0.080 Uiso 1 1 calc R . .
H14C H 0.9168 0.4564 0.2755 0.080 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
Cu1 O1 1.9641(19) . ?
Cu1 O1 1.9641(19) 5_776 ?
Cu1 N2 2.036(2) . ?
Cu1 N2 2.036(2) 5_776 ?
Cu1 O5 2.395(3) 5_776 ?
Cu1 O5 2.395(3) . ?
Cu2 O3 1.963(2) . ?
Cu2 O3 1.963(2) 7_766 ?
Cu2 N1 2.023(2) 2_755 ?
Cu2 N1 2.023(2) 8_566 ?
Cu2 O6 2.400(2) 7_766 ?
Cu2 O6 2.400(2) . ?
O1 C1 1.261(4) . ?
O2 C1 1.233(4) . ?
O3 C8 1.263(4) . ?
O4 C8 1.234(4) . ?
O5 H5A 0.8437 . ?
O5 H5B 0.8568 . ?
O6 H6A 0.8499 . ?
O6 H6B 0.8501 . ?
O7 H7A 0.8504 . ?
O7 H7B 0.8615 . ?
N1 C5 1.335(4) . ?
N1 C6 1.341(4) . ?
N1 Cu2 2.023(2) 2_755 ?
N2 C13 1.342(4) . ?
N2 C12 1.347(4) . ?
C1 C2 1.509(4) . ?
C2 C3 1.376(4) . ?
C2 C6 1.381(4) . ?
C3 C4 1.389(4) . ?
C3 H3 0.9300 . ?
C4 C5 1.380(4) . ?
C4 C7 1.507(5) . ?
C5 H5 0.9300 . ?
C6 H6 0.9300 . ?
C7 H7A' 0.9600 . ?
C7 H7B' 0.9600 . ?
C7 H7C' 0.9600 . ?
C8 C9 1.502(4) . ?
C9 C13 1.383(4) . ?
C9 C10 1.388(4) . ?
C10 C11 1.385(4) . ?
C10 H10 0.9300 . ?
C11 C12 1.381(4) . ?
C11 C14 1.512(4) . ?
C12 H12 0.9300 . ?
C13 H13 0.9300 . ?
C14 H14A 0.9600 . ?
C14 H14B 0.9600 . ?
C14 H14C 0.9600 . ?

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 Cu1 O1 180.000(1) . 5_776 ?
O1 Cu1 N2 89.78(9) . . ?
O1 Cu1 N2 90.22(9) 5_776 . ?
O1 Cu1 N2 90.22(9) . 5_776 ?
O1 Cu1 N2 89.78(9) 5_776 5_776 ?
N2 Cu1 N2 180.000(1) . 5_776 ?
O1 Cu1 O5 87.61(9) . 5_776 ?
O1 Cu1 O5 92.39(9) 5_776 5_776 ?
N2 Cu1 O5 88.20(10) . 5_776 ?
N2 Cu1 O5 91.80(10) 5_776 5_776 ?
O1 Cu1 O5 92.39(9) . . ?
O1 Cu1 O5 87.61(9) 5_776 . ?
N2 Cu1 O5 91.80(10) . . ?
N2 Cu1 O5 88.20(10) 5_776 . ?
O5 Cu1 O5 180.000(1) 5_776 . ?
O3 Cu2 O3 180.00(13) . 7_766 ?
O3 Cu2 N1 90.35(9) . 2_755 ?
O3 Cu2 N1 89.65(9) 7_766 2_755 ?
O3 Cu2 N1 89.65(9) . 8_566 ?
O3 Cu2 N1 90.35(9) 7_766 8_566 ?
N1 Cu2 N1 180.000(1) 2_755 8_566 ?
O3 Cu2 O6 84.79(8) . 7_766 ?
O3 Cu2 O6 95.21(8) 7_766 7_766 ?
N1 Cu2 O6 91.20(9) 2_755 7_766 ?
N1 Cu2 O6 88.80(9) 8_566 7_766 ?
O3 Cu2 O6 95.21(8) . . ?
O3 Cu2 O6 84.79(8) 7_766 . ?
N1 Cu2 O6 88.80(9) 2_755 . ?
N1 Cu2 O6 91.20(9) 8_566 . ?
O6 Cu2 O6 180.000(1) 7_766 . ?
C1 O1 Cu1 128.5(2) . . ?
C8 O3 Cu2 132.19(19) . . ?
Cu1 O5 H5A 135.8 . . ?
Cu1 O5 H5B 67.5 . . ?
H5A O5 H5B 114.6 . . ?
Cu2 O6 H6A 93.7 . . ?
Cu2 O6 H6B 123.3 . . ?
H6A O6 H6B 116.5 . . ?
H7A O7 H7B 116.5 . . ?
C5 N1 C6 118.3(3) . . ?
C5 N1 Cu2 121.4(2) . 2_755 ?
C6 N1 Cu2 120.2(2) . 2_755 ?
C13 N2 C12 117.6(3) . . ?
C13 N2 Cu1 121.05(19) . . ?
C12 N2 Cu1 121.4(2) . . ?
O2 C1 O1 126.5(3) . . ?
O2 C1 C2 118.8(3) . . ?
O1 C1 C2 114.7(3) . . ?
C3 C2 C6 118.5(3) . . ?
C3 C2 C1 122.1(3) . . ?
C6 C2 C1 119.4(3) . . ?
C2 C3 C4 120.3(3) . . ?
C2 C3 H3 119.8 . . ?
C4 C3 H3 119.8 . . ?
C5 C4 C3 117.0(3) . . ?
C5 C4 C7 121.0(3) . . ?
C3 C4 C7 122.0(3) . . ?
N1 C5 C4 123.7(3) . . ?
N1 C5 H5 118.1 . . ?
C4 C5 H5 118.1 . . ?
N1 C6 C2 122.2(3) . . ?
N1 C6 H6 118.9 . . ?
C2 C6 H6 118.9 . . ?
C4 C7 H7A' 109.5 . . ?
C4 C7 H7B' 109.5 . . ?
H7A' C7 H7B' 109.5 . . ?
C4 C7 H7C' 109.5 . . ?
H7A' C7 H7C' 109.5 . . ?
H7B' C7 H7C' 109.5 . . ?
O4 C8 O3 125.6(3) . . ?
O4 C8 C9 120.1(3) . . ?
O3 C8 C9 114.2(3) . . ?
C13 C9 C10 118.1(3) . . ?
C13 C9 C8 119.7(3) . . ?
C10 C9 C8 122.3(3) . . ?
C11 C10 C9 120.2(3) . . ?
C11 C10 H10 119.9 . . ?
C9 C10 H10 119.9 . . ?
C12 C11 C10 117.3(3) . . ?
C12 C11 C14 120.1(3) . . ?
C10 C11 C14 122.6(3) . . ?
N2 C12 C11 123.8(3) . . ?
N2 C12 H12 118.1 . . ?
C11 C12 H12 118.1 . . ?
N2 C13 C9 122.9(3) . . ?
N2 C13 H13 118.5 . . ?
C9 C13 H13 118.5 . . ?
C11 C14 H14A 109.5 . . ?
C11 C14 H14B 109.5 . . ?
H14A C14 H14B 109.5 . . ?
C11 C14 H14C 109.5 . . ?
H14A C14 H14C 109.5 . . ?
H14B C14 H14C 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
N2 Cu1 O1 C1 -58.9(3) . . . . ?
N2 Cu1 O1 C1 121.1(3) 5_776 . . . ?
O5 Cu1 O1 C1 -147.1(3) 5_776 . . . ?
O5 Cu1 O1 C1 32.9(3) . . . . ?
N1 Cu2 O3 C8 77.0(3) 2_755 . . . ?
N1 Cu2 O3 C8 -103.0(3) 8_566 . . . ?
O6 Cu2 O3 C8 168.2(3) 7_766 . . . ?
O6 Cu2 O3 C8 -11.8(3) . . . . ?
O1 Cu1 N2 C13 147.1(2) . . . . ?
O1 Cu1 N2 C13 -32.9(2) 5_776 . . . ?
O5 Cu1 N2 C13 -125.3(2) 5_776 . . . ?
O5 Cu1 N2 C13 54.7(2) . . . . ?
O1 Cu1 N2 C12 -32.0(2) . . . . ?
O1 Cu1 N2 C12 148.0(2) 5_776 . . . ?
O5 Cu1 N2 C12 55.6(2) 5_776 . . . ?
O5 Cu1 N2 C12 -124.4(2) . . . . ?
Cu1 O1 C1 O2 -31.1(5) . . . . ?
Cu1 O1 C1 C2 148.7(2) . . . . ?
O2 C1 C2 C3 -167.8(3) . . . . ?
O1 C1 C2 C3 12.4(4) . . . . ?
O2 C1 C2 C6 11.6(4) . . . . ?
O1 C1 C2 C6 -168.1(3) . . . . ?
C6 C2 C3 C4 -1.3(5) . . . . ?
C1 C2 C3 C4 178.2(3) . . . . ?
C2 C3 C4 C5 1.3(5) . . . . ?
C2 C3 C4 C7 -177.3(4) . . . . ?
C6 N1 C5 C4 0.4(5) . . . . ?
Cu2 N1 C5 C4 -175.5(3) 2_755 . . . ?
C3 C4 C5 N1 -0.9(6) . . . . ?
C7 C4 C5 N1 177.7(4) . . . . ?
C5 N1 C6 C2 -0.3(4) . . . . ?
Cu2 N1 C6 C2 175.6(2) 2_755 . . . ?
C3 C2 C6 N1 0.8(5) . . . . ?
C1 C2 C6 N1 -178.7(3) . . . . ?
Cu2 O3 C8 O4 5.0(5) . . . . ?
Cu2 O3 C8 C9 -174.32(19) . . . . ?
O4 C8 C9 C13 175.9(3) . . . . ?
O3 C8 C9 C13 -4.8(4) . . . . ?
O4 C8 C9 C10 -3.2(5) . . . . ?
O3 C8 C9 C10 176.1(3) . . . . ?
C13 C9 C10 C11 -1.1(5) . . . . ?
C8 C9 C10 C11 178.1(3) . . . . ?
C9 C10 C11 C12 -2.1(5) . . . . ?
C9 C10 C11 C14 178.9(3) . . . . ?
C13 N2 C12 C11 -2.7(4) . . . . ?
Cu1 N2 C12 C11 176.4(2) . . . . ?
C10 C11 C12 N2 4.1(5) . . . . ?
C14 C11 C12 N2 -176.8(3) . . . . ?
C12 N2 C13 C9 -0.8(4) . . . . ?
Cu1 N2 C13 C9 -179.9(2) . . . . ?
C10 C9 C13 N2 2.6(5) . . . . ?
C8 C9 C13 N2 -176.5(3) . . . . ?

_diffrn_measured_fraction_theta_max 1.000
_diffrn_reflns_theta_full        25.03
_diffrn_measured_fraction_theta_full 1.000
_refine_diff_density_max         0.629
_refine_diff_density_min         -0.480
_refine_diff_density_rms         0.065
_database_code_depnum_ccdc_archive 'CCDC 967575'
#######################################################################
#
#                 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_967576


_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C14 H18 Co N2 O7'
_chemical_formula_weight         385.23

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'
Co Co 0.3494 0.9721 '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                   26.420(2)
_cell_length_b                   8.6861(7)
_cell_length_c                   16.7178(13)
_cell_angle_alpha                90.00
_cell_angle_beta                 115.6680(10)
_cell_angle_gamma                90.00
_cell_volume                     3457.9(5)
_cell_formula_units_Z            8
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    4810
_cell_measurement_theta_min      2.50
_cell_measurement_theta_max      29.41

_exptl_crystal_description       BLOCK
_exptl_crystal_colour            RED
_exptl_crystal_size_max          0.30
_exptl_crystal_size_mid          0.26
_exptl_crystal_size_min          0.20
_exptl_crystal_density_meas      NONE
_exptl_crystal_density_diffrn    1.480
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1592
_exptl_absorpt_coefficient_mu    1.029
_exptl_absorpt_correction_type   MULTI-SCAN
_exptl_absorpt_correction_T_min  0.7615
_exptl_absorpt_correction_T_max  0.8206
_exptl_absorpt_process_details   SADABS

_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  '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            8569
_diffrn_reflns_av_R_equivalents  0.0171
_diffrn_reflns_av_sigmaI/netI    0.0190
_diffrn_reflns_limit_h_min       -31
_diffrn_reflns_limit_h_max       29
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_l_min       -10
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_theta_min         1.71
_diffrn_reflns_theta_max         25.03
_reflns_number_total             3049
_reflns_number_gt                2705
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'Bruker SMART'
_computing_cell_refinement       'Bruker SMART'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'

_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)+(0.0363P)²+2.5485P] 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         3049
_refine_ls_number_parameters     222
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0289
_refine_ls_R_factor_gt           0.0247
_refine_ls_wR_factor_ref         0.0687
_refine_ls_wR_factor_gt          0.0657
_refine_ls_goodness_of_fit_ref   1.061
_refine_ls_restrained_S_all      1.061
_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
Co1 Co 1.0000 0.0000 0.5000 0.02423(10) Uani 1 2 d S . .
Co2 Co 0.7500 0.2500 0.0000 0.02180(10) Uani 1 2 d S . .
O1 O 1.17099(5) 0.30542(15) 0.48079(9) 0.0318(3) Uani 1 1 d . . .
O2 O 1.15421(6) 0.54784(17) 0.43470(12) 0.0506(4) Uani 1 1 d . . .
O3 O 0.91849(5) 0.00720(15) 0.40387(8) 0.0319(3) Uani 1 1 d . . .
O4 O 0.92430(6) -0.03064(17) 0.27585(9) 0.0409(3) Uani 1 1 d . . .
O5 O 1.02528(5) -0.10932(16) 0.40988(9) 0.0368(3) Uani 1 1 d . . .
H5A H 1.0579 -0.1075 0.4116 0.055 Uiso 1 1 d R . .
H5B H 0.9995 -0.0919 0.3583 0.055 Uiso 1 1 d R . .
O6 O 0.73228(6) 0.48593(14) 0.01596(9) 0.0343(3) Uani 1 1 d . . .
H6A H 0.7030 0.5368 -0.0162 0.052 Uiso 1 1 d R . .
H6B H 0.7646 0.5268 0.0344 0.052 Uiso 1 1 d R . .
O7 O 0.87006(6) 0.85940(15) 0.09824(9) 0.0387(3) Uani 1 1 d . . .
H7A H 0.8659 0.7622 0.0961 0.058 Uiso 1 1 d R . .
H7B H 0.8840 0.8771 0.1537 0.058 Uiso 1 1 d R . .
N1 N 1.01463(6) 0.22211(18) 0.45485(10) 0.0296(3) Uani 1 1 d . . .
N2 N 0.77912(6) 0.21974(18) 0.13999(10) 0.0293(3) Uani 1 1 d . . .
C1 C 1.13936(7) 0.4200(2) 0.45064(12) 0.0289(4) Uani 1 1 d . . .
C2 C 1.07926(7) 0.3927(2) 0.43413(12) 0.0282(4) Uani 1 1 d . . .
C3 C 1.03616(8) 0.4964(2) 0.39053(13) 0.0330(4) Uani 1 1 d . . .
H3 H 1.0436 0.5888 0.3696 0.040 Uiso 1 1 calc R . .
C4 C 0.98180(8) 0.4623(2) 0.37807(13) 0.0330(4) Uani 1 1 d . . .
C5 C 0.97399(7) 0.3258(2) 0.41331(12) 0.0306(4) Uani 1 1 d . . .
H5 H 0.9382 0.3041 0.4079 0.037 Uiso 1 1 calc R . .
C6 C 1.06616(8) 0.2563(2) 0.46408(12) 0.0294(4) Uani 1 1 d . . .
H6 H 1.0947 0.1851 0.4920 0.035 Uiso 1 1 calc R . .
C7 C 0.93284(9) 0.5683(3) 0.32901(17) 0.0495(6) Uani 1 1 d . . .
H7A' H 0.9192 0.5523 0.2663 0.074 Uiso 1 1 calc R . .
H7B' H 0.9448 0.6733 0.3431 0.074 Uiso 1 1 calc R . .
H7C' H 0.9034 0.5469 0.3464 0.074 Uiso 1 1 calc R . .
C8 C 0.90077(7) 0.0203(2) 0.32101(12) 0.0277(4) Uani 1 1 d . . .
C9 C 0.84622(7) 0.1065(2) 0.27419(11) 0.0271(4) Uani 1 1 d . . .
C10 C 0.82841(7) 0.1514(2) 0.18666(11) 0.0276(4) Uani 1 1 d . . .
H10 H 0.8519 0.1330 0.1592 0.033 Uiso 1 1 calc R . .
C11 C 0.74633(8) 0.2480(2) 0.18087(13) 0.0363(5) Uani 1 1 d . . .
H11 H 0.7118 0.2951 0.1484 0.044 Uiso 1 1 calc R . .
C12 C 0.76073(9) 0.2112(3) 0.26863(14) 0.0406(5) Uani 1 1 d . . .
C13 C 0.81208(8) 0.1392(2) 0.31559(12) 0.0355(4) Uani 1 1 d . . .
H13 H 0.8235 0.1130 0.3748 0.043 Uiso 1 1 calc R . .
C14 C 0.72131(13) 0.2471(4) 0.31002(18) 0.0735(9) Uani 1 1 d . . .
H14A H 0.6860 0.2821 0.2649 0.110 Uiso 1 1 calc R . .
H14B H 0.7374 0.3260 0.3540 0.110 Uiso 1 1 calc R . .
H14C H 0.7154 0.1559 0.3374 0.110 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
Co1 O3 2.0556(12) 5_756 ?
Co1 O3 2.0556(12) . ?
Co1 O5 2.1188(13) 5_756 ?
Co1 O5 2.1188(13) . ?
Co1 N1 2.1666(15) 5_756 ?
Co1 N1 2.1666(15) . ?
Co2 O1 2.0276(12) 8_455 ?
Co2 O1 2.0276(12) 2_755 ?
Co2 N2 2.1397(15) . ?
Co2 N2 2.1397(15) 7_655 ?
Co2 O6 2.1444(12) . ?
Co2 O6 2.1444(12) 7_655 ?
O1 C1 1.256(2) . ?
O1 Co2 2.0276(12) 2_755 ?
O2 C1 1.244(2) . ?
O3 C8 1.261(2) . ?
O4 C8 1.249(2) . ?
O5 H5A 0.8499 . ?
O5 H5B 0.8499 . ?
O6 H6A 0.8499 . ?
O6 H6B 0.8500 . ?
O7 H7A 0.8500 . ?
O7 H7B 0.8499 . ?
N1 C6 1.335(2) . ?
N1 C5 1.342(2) . ?
N2 C10 1.333(2) . ?
N2 C11 1.338(2) . ?
C1 C2 1.508(2) . ?
C2 C3 1.385(3) . ?
C2 C6 1.387(2) . ?
C3 C4 1.391(3) . ?
C3 H3 0.9300 . ?
C4 C5 1.379(3) . ?
C4 C7 1.508(3) . ?
C5 H5 0.9300 . ?
C6 H6 0.9300 . ?
C7 H7A' 0.9600 . ?
C7 H7B' 0.9600 . ?
C7 H7C' 0.9600 . ?
C8 C9 1.507(2) . ?
C9 C13 1.384(3) . ?
C9 C10 1.385(2) . ?
C10 H10 0.9300 . ?
C11 C12 1.384(3) . ?
C11 H11 0.9300 . ?
C12 C13 1.387(3) . ?
C12 C14 1.512(3) . ?
C13 H13 0.9300 . ?
C14 H14A 0.9600 . ?
C14 H14B 0.9600 . ?
C14 H14C 0.9600 . ?

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 Co1 O3 180.00(5) 5_756 . ?
O3 Co1 O5 90.22(5) 5_756 5_756 ?
O3 Co1 O5 89.78(5) . 5_756 ?
O3 Co1 O5 89.78(5) 5_756 . ?
O3 Co1 O5 90.22(5) . . ?
O5 Co1 O5 180.000(1) 5_756 . ?
O3 Co1 N1 89.15(5) 5_756 5_756 ?
O3 Co1 N1 90.85(5) . 5_756 ?
O5 Co1 N1 89.58(6) 5_756 5_756 ?
O5 Co1 N1 90.42(6) . 5_756 ?
O3 Co1 N1 90.85(5) 5_756 . ?
O3 Co1 N1 89.15(5) . . ?
O5 Co1 N1 90.42(6) 5_756 . ?
O5 Co1 N1 89.58(6) . . ?
N1 Co1 N1 180.000(1) 5_756 . ?
O1 Co2 O1 180.00(7) 8_455 2_755 ?
O1 Co2 N2 90.11(6) 8_455 . ?
O1 Co2 N2 89.89(6) 2_755 . ?
O1 Co2 N2 89.89(6) 8_455 7_655 ?
O1 Co2 N2 90.11(6) 2_755 7_655 ?
N2 Co2 N2 180.00(12) . 7_655 ?
O1 Co2 O6 88.93(5) 8_455 . ?
O1 Co2 O6 91.07(5) 2_755 . ?
N2 Co2 O6 88.61(5) . . ?
N2 Co2 O6 91.39(5) 7_655 . ?
O1 Co2 O6 91.07(5) 8_455 7_655 ?
O1 Co2 O6 88.93(5) 2_755 7_655 ?
N2 Co2 O6 91.39(5) . 7_655 ?
N2 Co2 O6 88.61(5) 7_655 7_655 ?
O6 Co2 O6 180.00(8) . 7_655 ?
C1 O1 Co2 135.40(12) . 2_755 ?
C8 O3 Co1 128.80(12) . . ?
Co1 O5 H5A 126.5 . . ?
Co1 O5 H5B 106.3 . . ?
H5A O5 H5B 112.7 . . ?
Co2 O6 H6A 127.3 . . ?
Co2 O6 H6B 101.8 . . ?
H6A O6 H6B 120.6 . . ?
H7A O7 H7B 102.3 . . ?
C6 N1 C5 117.24(16) . . ?
C6 N1 Co1 118.99(12) . . ?
C5 N1 Co1 123.67(12) . . ?
C10 N2 C11 117.85(16) . . ?
C10 N2 Co2 119.48(12) . . ?
C11 N2 Co2 122.04(12) . . ?
O2 C1 O1 125.18(17) . . ?
O2 C1 C2 120.38(17) . . ?
O1 C1 C2 114.45(16) . . ?
C3 C2 C6 117.92(16) . . ?
C3 C2 C1 123.68(16) . . ?
C6 C2 C1 118.40(16) . . ?
C2 C3 C4 120.04(17) . . ?
C2 C3 H3 120.0 . . ?
C4 C3 H3 120.0 . . ?
C5 C4 C3 117.07(17) . . ?
C5 C4 C7 120.37(18) . . ?
C3 C4 C7 122.56(18) . . ?
N1 C5 C4 124.34(17) . . ?
N1 C5 H5 117.8 . . ?
C4 C5 H5 117.8 . . ?
N1 C6 C2 123.33(17) . . ?
N1 C6 H6 118.3 . . ?
C2 C6 H6 118.3 . . ?
C4 C7 H7A' 109.5 . . ?
C4 C7 H7B' 109.5 . . ?
H7A' C7 H7B' 109.5 . . ?
C4 C7 H7C' 109.5 . . ?
H7A' C7 H7C' 109.5 . . ?
H7B' C7 H7C' 109.5 . . ?
O4 C8 O3 125.95(17) . . ?
O4 C8 C9 118.46(16) . . ?
O3 C8 C9 115.60(16) . . ?
C13 C9 C10 118.29(16) . . ?
C13 C9 C8 121.73(16) . . ?
C10 C9 C8 119.95(16) . . ?
N2 C10 C9 122.85(16) . . ?
N2 C10 H10 118.6 . . ?
C9 C10 H10 118.6 . . ?
N2 C11 C12 123.88(18) . . ?
N2 C11 H11 118.1 . . ?
C12 C11 H11 118.1 . . ?
C11 C12 C13 117.16(18) . . ?
C11 C12 C14 120.66(19) . . ?
C13 C12 C14 122.18(19) . . ?
C9 C13 C12 119.93(17) . . ?
C9 C13 H13 120.0 . . ?
C12 C13 H13 120.0 . . ?
C12 C14 H14A 109.5 . . ?
C12 C14 H14B 109.5 . . ?
H14A C14 H14B 109.5 . . ?
C12 C14 H14C 109.5 . . ?
H14A C14 H14C 109.5 . . ?
H14B C14 H14C 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
O5 Co1 O3 C8 148.12(15) 5_756 . . . ?
O5 Co1 O3 C8 -31.88(15) . . . . ?
N1 Co1 O3 C8 -122.31(15) 5_756 . . . ?
N1 Co1 O3 C8 57.69(15) . . . . ?
O3 Co1 N1 C6 29.52(14) 5_756 . . . ?
O3 Co1 N1 C6 -150.48(14) . . . . ?
O5 Co1 N1 C6 119.75(14) 5_756 . . . ?
O5 Co1 N1 C6 -60.25(14) . . . . ?
O3 Co1 N1 C5 -154.21(15) 5_756 . . . ?
O3 Co1 N1 C5 25.79(15) . . . . ?
O5 Co1 N1 C5 -63.98(15) 5_756 . . . ?
O5 Co1 N1 C5 116.02(15) . . . . ?
O1 Co2 N2 C10 139.68(14) 8_455 . . . ?
O1 Co2 N2 C10 -40.32(14) 2_755 . . . ?
O6 Co2 N2 C10 -131.40(14) . . . . ?
O6 Co2 N2 C10 48.60(14) 7_655 . . . ?
O1 Co2 N2 C11 -31.02(16) 8_455 . . . ?
O1 Co2 N2 C11 148.98(16) 2_755 . . . ?
O6 Co2 N2 C11 57.90(16) . . . . ?
O6 Co2 N2 C11 -122.10(16) 7_655 . . . ?
Co2 O1 C1 O2 -11.2(3) 2_755 . . . ?
Co2 O1 C1 C2 168.88(12) 2_755 . . . ?
O2 C1 C2 C3 8.8(3) . . . . ?
O1 C1 C2 C3 -171.27(18) . . . . ?
O2 C1 C2 C6 -171.22(19) . . . . ?
O1 C1 C2 C6 8.7(2) . . . . ?
C6 C2 C3 C4 0.1(3) . . . . ?
C1 C2 C3 C4 -179.97(18) . . . . ?
C2 C3 C4 C5 2.1(3) . . . . ?
C2 C3 C4 C7 -178.3(2) . . . . ?
C6 N1 C5 C4 1.6(3) . . . . ?
Co1 N1 C5 C4 -174.70(15) . . . . ?
C3 C4 C5 N1 -3.1(3) . . . . ?
C7 C4 C5 N1 177.3(2) . . . . ?
C5 N1 C6 C2 0.9(3) . . . . ?
Co1 N1 C6 C2 177.36(14) . . . . ?
C3 C2 C6 N1 -1.7(3) . . . . ?
C1 C2 C6 N1 178.39(17) . . . . ?
Co1 O3 C8 O4 32.3(3) . . . . ?
Co1 O3 C8 C9 -147.45(12) . . . . ?
O4 C8 C9 C13 166.78(18) . . . . ?
O3 C8 C9 C13 -13.5(3) . . . . ?
O4 C8 C9 C10 -11.4(3) . . . . ?
O3 C8 C9 C10 168.31(16) . . . . ?
C11 N2 C10 C9 1.2(3) . . . . ?
Co2 N2 C10 C9 -169.86(14) . . . . ?
C13 C9 C10 N2 -2.3(3) . . . . ?
C8 C9 C10 N2 175.95(16) . . . . ?
C10 N2 C11 C12 0.4(3) . . . . ?
Co2 N2 C11 C12 171.23(17) . . . . ?
N2 C11 C12 C13 -0.8(3) . . . . ?
N2 C11 C12 C14 179.9(2) . . . . ?
C10 C9 C13 C12 1.8(3) . . . . ?
C8 C9 C13 C12 -176.41(18) . . . . ?
C11 C12 C13 C9 -0.4(3) . . . . ?
C14 C12 C13 C9 178.9(2) . . . . ?

_diffrn_measured_fraction_theta_max 1.000
_diffrn_reflns_theta_full        25.03
_diffrn_measured_fraction_theta_full 1.000
_refine_diff_density_max         0.306
_refine_diff_density_min         -0.205
_refine_diff_density_rms         0.046
_database_code_depnum_ccdc_archive 'CCDC 967576'
#######################################################################
#
#                 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_967577

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C14 H16 Mn N2 O6'
_chemical_formula_weight         363.23

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'
Mn Mn 0.3368 0.7283 '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                   10.0704(5)
_cell_length_b                   10.1890(5)
_cell_length_c                   7.1745(4)
_cell_angle_alpha                90.00
_cell_angle_beta                 101.7970(10)
_cell_angle_gamma                90.00
_cell_volume                     720.61(6)
_cell_formula_units_Z            2
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    2968
_cell_measurement_theta_min      2.88
_cell_measurement_theta_max      30.40

_exptl_crystal_description       BLOCK
_exptl_crystal_colour            COLORLESS
_exptl_crystal_size_max          0.32
_exptl_crystal_size_mid          0.28
_exptl_crystal_size_min          0.26
_exptl_crystal_density_meas      NONE
_exptl_crystal_density_diffrn    1.674
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             374
_exptl_absorpt_coefficient_mu    0.951
_exptl_absorpt_correction_type   MULTI-SCAN
_exptl_absorpt_correction_T_min  0.7507
_exptl_absorpt_correction_T_max  0.8181
_exptl_absorpt_process_details   SADABS

_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  '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            3570
_diffrn_reflns_av_R_equivalents  0.0120
_diffrn_reflns_av_sigmaI/netI    0.0128
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_l_min       -7
_diffrn_reflns_limit_l_max       8
_diffrn_reflns_theta_min         2.07
_diffrn_reflns_theta_max         25.03
_reflns_number_total             1268
_reflns_number_gt                1207
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'Bruker SMART'
_computing_cell_refinement       'Bruker SMART'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'

_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)+(0.0339P)²+0.3433P] 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         1268
_refine_ls_number_parameters     107
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0240
_refine_ls_R_factor_gt           0.0230
_refine_ls_wR_factor_ref         0.0639
_refine_ls_wR_factor_gt          0.0632
_refine_ls_goodness_of_fit_ref   1.099
_refine_ls_restrained_S_all      1.099
_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
Mn1 Mn 0.0000 0.5000 0.0000 0.01868(13) Uani 1 2 d S . .
O1 O 0.20831(11) 1.12025(10) 0.05806(16) 0.0253(3) Uani 1 1 d . . .
O2 O 0.07438(12) 1.04404(12) 0.24410(16) 0.0276(3) Uani 1 1 d . . .
O3 O 0.15668(12) 0.36901(11) 0.15794(16) 0.0279(3) Uani 1 1 d . . .
H3A H 0.1660 0.2907 0.1217 0.042 Uiso 1 1 d R . .
H3B H 0.1737 0.3788 0.2782 0.042 Uiso 1 1 d R . .
N1 N 0.15693(13) 0.66183(13) 0.08166(19) 0.0211(3) Uani 1 1 d . . .
C1 C 0.28563(16) 0.64097(15) 0.0650(2) 0.0226(3) Uani 1 1 d . . .
H1 H 0.3129 0.5548 0.0522 0.027 Uiso 1 1 calc R . .
C2 C 0.38033(16) 0.73967(16) 0.0658(2) 0.0226(3) Uani 1 1 d . . .
C3 C 0.33669(16) 0.86765(15) 0.0827(2) 0.0223(3) Uani 1 1 d . . .
H3 H 0.3950 0.9375 0.0759 0.027 Uiso 1 1 calc R . .
C4 C 0.20615(16) 0.89160(15) 0.1097(2) 0.0194(3) Uani 1 1 d . . .
C5 C 0.12025(16) 0.78522(15) 0.1093(2) 0.0205(3) Uani 1 1 d . . .
H5 H 0.0331 0.8004 0.1292 0.025 Uiso 1 1 calc R . .
C6 C 0.52378(17) 0.70692(19) 0.0503(3) 0.0330(4) Uani 1 1 d . . .
H6A H 0.5703 0.6673 0.1668 0.050 Uiso 1 1 calc R . .
H6B H 0.5701 0.7858 0.0274 0.050 Uiso 1 1 calc R . .
H6C H 0.5222 0.6468 -0.0532 0.050 Uiso 1 1 calc R . .
C7 C 0.15875(16) 1.02892(15) 0.1400(2) 0.0194(3) 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
Mn1 O2 2.1669(11) 4_575 ?
Mn1 O2 2.1669(11) 2_545 ?
Mn1 O3 2.1963(11) . ?
Mn1 O3 2.1963(11) 3_565 ?
Mn1 N1 2.2762(13) 3_565 ?
Mn1 N1 2.2762(13) . ?
O1 C7 1.2571(19) . ?
O2 C7 1.2504(19) . ?
O2 Mn1 2.1669(11) 2 ?
O3 H3A 0.8502 . ?
O3 H3B 0.8502 . ?
N1 C5 1.337(2) . ?
N1 C1 1.343(2) . ?
C1 C2 1.385(2) . ?
C1 H1 0.9300 . ?
C2 C3 1.389(2) . ?
C2 C6 1.509(2) . ?
C3 C4 1.389(2) . ?
C3 H3 0.9300 . ?
C4 C5 1.386(2) . ?
C4 C7 1.508(2) . ?
C5 H5 0.9300 . ?
C6 H6A 0.9600 . ?
C6 H6B 0.9600 . ?
C6 H6C 0.9600 . ?

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
O2 Mn1 O2 180.00(6) 4_575 2_545 ?
O2 Mn1 O3 88.57(4) 4_575 . ?
O2 Mn1 O3 91.43(4) 2_545 . ?
O2 Mn1 O3 91.43(4) 4_575 3_565 ?
O2 Mn1 O3 88.57(4) 2_545 3_565 ?
O3 Mn1 O3 180.0 . 3_565 ?
O2 Mn1 N1 88.51(4) 4_575 3_565 ?
O2 Mn1 N1 91.49(4) 2_545 3_565 ?
O3 Mn1 N1 94.61(4) . 3_565 ?
O3 Mn1 N1 85.39(5) 3_565 3_565 ?
O2 Mn1 N1 91.49(4) 4_575 . ?
O2 Mn1 N1 88.51(4) 2_545 . ?
O3 Mn1 N1 85.39(5) . . ?
O3 Mn1 N1 94.61(4) 3_565 . ?
N1 Mn1 N1 180.0 3_565 . ?
C7 O2 Mn1 151.11(11) . 2 ?
Mn1 O3 H3A 121.7 . . ?
Mn1 O3 H3B 115.3 . . ?
H3A O3 H3B 114.1 . . ?
C5 N1 C1 117.60(13) . . ?
C5 N1 Mn1 121.41(10) . . ?
C1 N1 Mn1 119.64(10) . . ?
N1 C1 C2 124.14(14) . . ?
N1 C1 H1 117.9 . . ?
C2 C1 H1 117.9 . . ?
C1 C2 C3 116.86(14) . . ?
C1 C2 C6 120.53(15) . . ?
C3 C2 C6 122.60(15) . . ?
C4 C3 C2 120.16(14) . . ?
C4 C3 H3 119.9 . . ?
C2 C3 H3 119.9 . . ?
C5 C4 C3 118.06(14) . . ?
C5 C4 C7 120.64(14) . . ?
C3 C4 C7 121.30(13) . . ?
N1 C5 C4 122.98(14) . . ?
N1 C5 H5 118.5 . . ?
C4 C5 H5 118.5 . . ?
C2 C6 H6A 109.5 . . ?
C2 C6 H6B 109.5 . . ?
H6A C6 H6B 109.5 . . ?
C2 C6 H6C 109.5 . . ?
H6A C6 H6C 109.5 . . ?
H6B C6 H6C 109.5 . . ?
O2 C7 O1 124.84(15) . . ?
O2 C7 C4 118.31(14) . . ?
O1 C7 C4 116.85(14) . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
O2 Mn1 N1 C5 122.70(12) 4_575 . . . ?
O2 Mn1 N1 C5 -57.30(12) 2_545 . . . ?
O3 Mn1 N1 C5 -148.86(12) . . . . ?
O3 Mn1 N1 C5 31.14(12) 3_565 . . . ?
O2 Mn1 N1 C1 -43.70(12) 4_575 . . . ?
O2 Mn1 N1 C1 136.30(12) 2_545 . . . ?
O3 Mn1 N1 C1 44.75(12) . . . . ?
O3 Mn1 N1 C1 -135.25(12) 3_565 . . . ?
C5 N1 C1 C2 -3.2(2) . . . . ?
Mn1 N1 C1 C2 163.74(12) . . . . ?
N1 C1 C2 C3 -0.8(2) . . . . ?
N1 C1 C2 C6 178.75(15) . . . . ?
C1 C2 C3 C4 4.0(2) . . . . ?
C6 C2 C3 C4 -175.55(15) . . . . ?
C2 C3 C4 C5 -3.2(2) . . . . ?
C2 C3 C4 C7 176.38(14) . . . . ?
C1 N1 C5 C4 4.1(2) . . . . ?
Mn1 N1 C5 C4 -162.61(12) . . . . ?
C3 C4 C5 N1 -1.0(2) . . . . ?
C7 C4 C5 N1 179.47(14) . . . . ?
Mn1 O2 C7 O1 -136.62(19) 2 . . . ?
Mn1 O2 C7 C4 43.1(3) 2 . . . ?
C5 C4 C7 O2 31.7(2) . . . . ?
C3 C4 C7 O2 -147.81(15) . . . . ?
C5 C4 C7 O1 -148.55(15) . . . . ?
C3 C4 C7 O1 31.9(2) . . . . ?

_diffrn_measured_fraction_theta_max 0.996
_diffrn_reflns_theta_full        25.03
_diffrn_measured_fraction_theta_full 0.996
_refine_diff_density_max         0.234
_refine_diff_density_min         -0.237
_refine_diff_density_rms         0.049
_database_code_depnum_ccdc_archive 'CCDC 967577'
#######################################################################
#
#                 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_967578


_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C14 H12 N2 O4 Pb'
_chemical_formula_weight         479.45

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'
Pb Pb -3.3944 10.1111 '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                   12.912(2)
_cell_length_b                   9.1366(16)
_cell_length_c                   14.7843(17)
_cell_angle_alpha                90.00
_cell_angle_beta                 122.411(9)
_cell_angle_gamma                90.00
_cell_volume                     1472.4(4)
_cell_formula_units_Z            4
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    2988
_cell_measurement_theta_min      2.76
_cell_measurement_theta_max      27.12

_exptl_crystal_description       BLOCK
_exptl_crystal_colour            COLORLESS
_exptl_crystal_size_max          0.38
_exptl_crystal_size_mid          0.32
_exptl_crystal_size_min          0.30
_exptl_crystal_density_meas      NONE
_exptl_crystal_density_diffrn    2.163
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             896
_exptl_absorpt_coefficient_mu    11.474
_exptl_absorpt_correction_type   MULTI-SCAN
_exptl_absorpt_correction_T_min  0.0974
_exptl_absorpt_correction_T_max  0.1302
_exptl_absorpt_process_details   SADABS

_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  '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            7283
_diffrn_reflns_av_R_equivalents  0.0449
_diffrn_reflns_av_sigmaI/netI    0.0486
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_theta_min         2.76
_diffrn_reflns_theta_max         25.03
_reflns_number_total             2589
_reflns_number_gt                2199
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'Bruker SMART'
_computing_cell_refinement       'Bruker SMART'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'

_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)+(0.0434P)²+0.2890P] 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     SHELXL
_refine_ls_extinction_coef       0.0039(3)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_number_reflns         2589
_refine_ls_number_parameters     193
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0378
_refine_ls_R_factor_gt           0.0300
_refine_ls_wR_factor_ref         0.0794
_refine_ls_wR_factor_gt          0.0743
_refine_ls_goodness_of_fit_ref   1.017
_refine_ls_restrained_S_all      1.017
_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
Pb1 Pb 0.185242(19) 0.56840(2) 0.585282(16) 0.03285(14) Uani 1 1 d . . .
O1 O 0.3355(5) 0.5805(5) 0.8015(5) 0.0550(14) Uani 1 1 d . . .
O2 O 0.3449(4) 0.7379(5) 0.6913(4) 0.0515(13) Uani 1 1 d . . .
O3 O 0.1454(4) 0.7007(5) 0.4277(3) 0.0463(12) Uani 1 1 d . . .
O4 O -0.0288(6) 0.5882(7) 0.3751(5) 0.0684(18) Uani 1 1 d . . .
N1 N 0.6398(6) 0.9515(6) 0.9438(5) 0.0453(15) Uani 1 1 d . . .
N2 N 0.0589(5) 0.7592(6) 0.6157(4) 0.0447(14) Uani 1 1 d . . .
C1 C 0.3806(6) 0.6900(7) 0.7846(6) 0.0409(16) Uani 1 1 d . . .
C2 C 0.4810(6) 0.7732(7) 0.8783(5) 0.0358(14) Uani 1 1 d . . .
C3 C 0.5109(6) 0.7457(7) 0.9822(5) 0.0431(16) Uani 1 1 d . . .
H3 H 0.4672 0.6760 0.9943 0.052 Uiso 1 1 calc R . .
C4 C 0.6052(7) 0.8216(7) 1.0674(5) 0.0455(16) Uani 1 1 d . . .
C5 C 0.6668(7) 0.9230(7) 1.0433(6) 0.0463(18) Uani 1 1 d . . .
H5 H 0.7311 0.9747 1.0997 0.056 Uiso 1 1 calc R . .
C6 C 0.5479(6) 0.8781(7) 0.8634(5) 0.0393(15) Uani 1 1 d . . .
H6 H 0.5276 0.8980 0.7940 0.047 Uiso 1 1 calc R . .
C7 C 0.6419(8) 0.7970(9) 1.1813(6) 0.064(2) Uani 1 1 d . . .
H7A H 0.6751 0.7003 1.2033 0.096 Uiso 1 1 calc R . .
H7B H 0.5712 0.8072 1.1865 0.096 Uiso 1 1 calc R . .
H7C H 0.7026 0.8678 1.2268 0.096 Uiso 1 1 calc R . .
C8 C 0.0429(6) 0.6496(7) 0.3564(5) 0.0347(14) Uani 1 1 d . . .
C9 C 0.0069(5) 0.6603(6) 0.2410(4) 0.0354(14) Uani 1 1 d . . .
C10 C 0.0830(6) 0.7685(7) 0.7161(5) 0.0403(15) Uani 1 1 d . . .
H10 H 0.1542 0.7250 0.7713 0.048 Uiso 1 1 calc R . .
C11 C -0.0459(6) 0.8230(7) 0.5372(5) 0.0416(16) Uani 1 1 d . . .
H11 H -0.0643 0.8168 0.4673 0.050 Uiso 1 1 calc R . .
C12 C -0.1261(6) 0.8960(7) 0.5545(5) 0.0374(15) Uani 1 1 d . . .
C13 C -0.0995(6) 0.5958(6) 0.1584(5) 0.0356(14) Uani 1 1 d . . .
H13 H -0.1525 0.5474 0.1727 0.043 Uiso 1 1 calc R . .
C14 C -0.2404(7) 0.9664(8) 0.4628(6) 0.056(2) Uani 1 1 d . . .
H14A H -0.3091 0.9019 0.4390 0.084 Uiso 1 1 calc R . .
H14B H -0.2291 0.9847 0.4047 0.084 Uiso 1 1 calc R . .
H14C H -0.2557 1.0571 0.4864 0.084 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
Pb1 O2 2.375(4) . ?
Pb1 O3 2.423(4) . ?
Pb1 N2 2.587(5) . ?
Pb1 O1 2.710(6) . ?
Pb1 N1 2.734(6) 2_646 ?
O1 C1 1.249(8) . ?
O2 C1 1.275(8) . ?
O3 C8 1.260(7) . ?
O4 C8 1.234(8) . ?
N1 C6 1.326(9) . ?
N1 C5 1.342(10) . ?
N1 Pb1 2.734(6) 2_656 ?
N2 C10 1.346(8) . ?
N2 C11 1.354(8) . ?
C1 C2 1.500(9) . ?
C2 C6 1.385(9) . ?
C2 C3 1.392(9) . ?
C3 C4 1.380(9) . ?
C3 H3 0.9300 . ?
C4 C5 1.387(10) . ?
C4 C7 1.502(9) . ?
C5 H5 0.9300 . ?
C6 H6 0.9300 . ?
C7 H7A 0.9600 . ?
C7 H7B 0.9600 . ?
C7 H7C 0.9600 . ?
C8 C9 1.512(8) . ?
C9 C10 1.383(8) 4_575 ?
C9 C13 1.388(8) . ?
C10 C9 1.383(8) 4_576 ?
C10 H10 0.9300 . ?
C11 C12 1.367(9) . ?
C11 H11 0.9300 . ?
C12 C13 1.384(9) 4_576 ?
C12 C14 1.511(9) . ?
C13 C12 1.384(9) 4_575 ?
C13 H13 0.9300 . ?
C14 H14A 0.9600 . ?
C14 H14B 0.9600 . ?
C14 H14C 0.9600 . ?

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
O2 Pb1 O3 88.34(15) . . ?
O2 Pb1 N2 81.43(18) . . ?
O3 Pb1 N2 90.15(17) . . ?
O2 Pb1 O1 51.37(15) . . ?
O3 Pb1 O1 139.70(14) . . ?
N2 Pb1 O1 83.50(17) . . ?
O2 Pb1 N1 81.98(18) . 2_646 ?
O3 Pb1 N1 79.09(17) . 2_646 ?
N2 Pb1 N1 160.45(19) . 2_646 ?
O1 Pb1 N1 94.13(18) . 2_646 ?
C1 O1 Pb1 85.0(4) . . ?
C1 O2 Pb1 100.0(4) . . ?
C8 O3 Pb1 101.9(4) . . ?
C6 N1 C5 117.8(6) . . ?
C6 N1 Pb1 118.3(5) . 2_656 ?
C5 N1 Pb1 119.8(5) . 2_656 ?
C10 N2 C11 116.9(6) . . ?
C10 N2 Pb1 116.1(4) . . ?
C11 N2 Pb1 125.1(4) . . ?
O1 C1 O2 123.6(6) . . ?
O1 C1 C2 119.1(6) . . ?
O2 C1 C2 117.2(6) . . ?
C6 C2 C3 118.2(6) . . ?
C6 C2 C1 120.5(6) . . ?
C3 C2 C1 121.3(6) . . ?
C4 C3 C2 120.2(6) . . ?
C4 C3 H3 119.9 . . ?
C2 C3 H3 119.9 . . ?
C3 C4 C5 116.7(6) . . ?
C3 C4 C7 122.8(7) . . ?
C5 C4 C7 120.6(7) . . ?
N1 C5 C4 124.2(7) . . ?
N1 C5 H5 117.9 . . ?
C4 C5 H5 117.9 . . ?
N1 C6 C2 122.8(6) . . ?
N1 C6 H6 118.6 . . ?
C2 C6 H6 118.6 . . ?
C4 C7 H7A 109.5 . . ?
C4 C7 H7B 109.5 . . ?
H7A C7 H7B 109.5 . . ?
C4 C7 H7C 109.5 . . ?
H7A C7 H7C 109.5 . . ?
H7B C7 H7C 109.5 . . ?
O4 C8 O3 124.0(6) . . ?
O4 C8 C9 117.9(6) . . ?
O3 C8 C9 118.0(5) . . ?
C10 C9 C13 118.3(6) 4_575 . ?
C10 C9 C8 119.9(5) 4_575 . ?
C13 C9 C8 121.8(6) . . ?
N2 C10 C9 123.0(6) . 4_576 ?
N2 C10 H10 118.5 . . ?
C9 C10 H10 118.5 4_576 . ?
N2 C11 C12 124.0(6) . . ?
N2 C11 H11 118.0 . . ?
C12 C11 H11 118.0 . . ?
C11 C12 C13 118.1(6) . 4_576 ?
C11 C12 C14 120.9(6) . . ?
C13 C12 C14 121.0(6) 4_576 . ?
C12 C13 C9 119.6(6) 4_575 . ?
C12 C13 H13 120.2 4_575 . ?
C9 C13 H13 120.2 . . ?
C12 C14 H14A 109.5 . . ?
C12 C14 H14B 109.5 . . ?
H14A C14 H14B 109.5 . . ?
C12 C14 H14C 109.5 . . ?
H14A C14 H14C 109.5 . . ?
H14B C14 H14C 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 Pb1 O1 C1 0.6(4) . . . . ?
O3 Pb1 O1 C1 -1.1(5) . . . . ?
N2 Pb1 O1 C1 -83.6(4) . . . . ?
N1 Pb1 O1 C1 76.9(4) 2_646 . . . ?
O3 Pb1 O2 C1 178.3(4) . . . . ?
N2 Pb1 O2 C1 87.9(4) . . . . ?
O1 Pb1 O2 C1 -0.6(4) . . . . ?
N1 Pb1 O2 C1 -102.5(4) 2_646 . . . ?
O2 Pb1 O3 C8 -166.5(4) . . . . ?
N2 Pb1 O3 C8 -85.1(4) . . . . ?
O1 Pb1 O3 C8 -165.2(4) . . . . ?
N1 Pb1 O3 C8 111.3(4) 2_646 . . . ?
O2 Pb1 N2 C10 -69.6(5) . . . . ?
O3 Pb1 N2 C10 -157.9(5) . . . . ?
O1 Pb1 N2 C10 -17.8(5) . . . . ?
N1 Pb1 N2 C10 -101.8(7) 2_646 . . . ?
O2 Pb1 N2 C11 126.9(6) . . . . ?
O3 Pb1 N2 C11 38.6(5) . . . . ?
O1 Pb1 N2 C11 178.7(6) . . . . ?
N1 Pb1 N2 C11 94.6(7) 2_646 . . . ?
Pb1 O1 C1 O2 -1.1(6) . . . . ?
Pb1 O1 C1 C2 177.8(5) . . . . ?
Pb1 O2 C1 O1 1.2(7) . . . . ?
Pb1 O2 C1 C2 -177.7(5) . . . . ?
O1 C1 C2 C6 168.3(6) . . . . ?
O2 C1 C2 C6 -12.7(9) . . . . ?
O1 C1 C2 C3 -10.5(10) . . . . ?
O2 C1 C2 C3 168.4(6) . . . . ?
C6 C2 C3 C4 -0.1(10) . . . . ?
C1 C2 C3 C4 178.7(6) . . . . ?
C2 C3 C4 C5 -0.5(10) . . . . ?
C2 C3 C4 C7 180.0(7) . . . . ?
C6 N1 C5 C4 0.2(11) . . . . ?
Pb1 N1 C5 C4 -156.6(6) 2_656 . . . ?
C3 C4 C5 N1 0.5(11) . . . . ?
C7 C4 C5 N1 -180.0(7) . . . . ?
C5 N1 C6 C2 -0.9(11) . . . . ?
Pb1 N1 C6 C2 156.3(5) 2_656 . . . ?
C3 C2 C6 N1 0.9(10) . . . . ?
C1 C2 C6 N1 -178.0(6) . . . . ?
Pb1 O3 C8 O4 20.5(8) . . . . ?
Pb1 O3 C8 C9 -157.7(5) . . . . ?
O4 C8 C9 C10 178.4(7) . . . 4_575 ?
O3 C8 C9 C10 -3.3(9) . . . 4_575 ?
O4 C8 C9 C13 -3.9(10) . . . . ?
O3 C8 C9 C13 174.4(6) . . . . ?
C11 N2 C10 C9 -0.4(10) . . . 4_576 ?
Pb1 N2 C10 C9 -165.3(5) . . . 4_576 ?
C10 N2 C11 C12 0.6(10) . . . . ?
Pb1 N2 C11 C12 164.0(5) . . . . ?
N2 C11 C12 C13 -0.6(10) . . . 4_576 ?
N2 C11 C12 C14 179.1(6) . . . . ?
C10 C9 C13 C12 0.1(9) 4_575 . . 4_575 ?
C8 C9 C13 C12 -177.6(6) . . . 4_575 ?

_diffrn_measured_fraction_theta_max 0.998
_diffrn_reflns_theta_full        25.03
_diffrn_measured_fraction_theta_full 0.998
_refine_diff_density_max         1.834
_refine_diff_density_min         -1.810
_refine_diff_density_rms         0.153



#===END
_database_code_depnum_ccdc_archive 'CCDC 967578'
