# Supplementary Material for CrystEngComm
# This journal is (c) The Royal Society of Chemistry 2009

data_global
_journal_name_full               CrystEngComm

_journal_coden_Cambridge         1350

_publ_contact_author_name        'Ming-Liang Tong'
_publ_contact_author_email       TONGML@MAIL.SYSU.EDU.CN

_publ_section_title              
;
Hydrothermal In Situ Ligand Reaction:
Copper(II)-Mediated Stepwise Oxidation of 2,3,5- and
2,4,6-Trimethylpyridine to Pyridinecarboxylates
;
loop_
_publ_author_name
'Ming-Liang Tong'
'Cui-Jin Li'
'Zhuo-jia Lin'
'Yong-Cong Ou'
'Lei Yun'

# Attachment 'CIF_B911463G.cif'

data_1
_database_code_depnum_ccdc_archive 'CCDC 727580'

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C16 H16 Cu N2 O4'
_chemical_formula_weight         363.85

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   P21/C

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

_cell_length_a                   5.0333(8)
_cell_length_b                   13.995(2)
_cell_length_c                   10.7354(17)
_cell_angle_alpha                90.00
_cell_angle_beta                 97.733(2)
_cell_angle_gamma                90.00
_cell_volume                     749.4(2)
_cell_formula_units_Z            2
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    ?
_cell_measurement_theta_min      ?
_cell_measurement_theta_max      ?

_exptl_crystal_description       block
_exptl_crystal_colour            dark-blue
_exptl_crystal_size_max          0.18
_exptl_crystal_size_mid          0.11
_exptl_crystal_size_min          0.08
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.613
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             374
_exptl_absorpt_coefficient_mu    1.479
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.7787
_exptl_absorpt_correction_T_max  0.8896
_exptl_absorpt_process_details   'SADABS (Bruker, 2002)'

_exptl_special_details           
;
?
;

_diffrn_ambient_temperature      293(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Bruker SMART CCD area detector'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            2597
_diffrn_reflns_av_R_equivalents  0.0165
_diffrn_reflns_av_sigmaI/netI    0.0305
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_limit_l_max       5
_diffrn_reflns_theta_min         2.40
_diffrn_reflns_theta_max         26.00
_reflns_number_total             1415
_reflns_number_gt                1216
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'Bruker SMART (Bruker, 1998)'
_computing_cell_refinement       'Bruker SMART (Bruker, 1998)'
_computing_data_reduction        'Bruker SAINT + & SHELXTL (Bruker, 1998)'
_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)+(0.0661P)²+0.3116P] 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         1415
_refine_ls_number_parameters     108
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0445
_refine_ls_R_factor_gt           0.0380
_refine_ls_wR_factor_ref         0.1064
_refine_ls_wR_factor_gt          0.1013
_refine_ls_goodness_of_fit_ref   1.037
_refine_ls_restrained_S_all      1.037
_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 0.0000 0.0000 0.0000 0.0291(2) Uani 1 2 d S . .
O1 O -0.2641(4) -0.05369(14) 0.09511(18) 0.0334(5) Uani 1 1 d . . .
O2 O -0.5944(5) -0.01042(13) 0.2011(2) 0.0436(6) Uani 1 1 d . . .
N1 N -0.1137(4) 0.12159(15) 0.0678(2) 0.0272(5) Uani 1 1 d . . .
C1 C -0.2918(5) 0.10917(18) 0.1498(2) 0.0269(6) Uani 1 1 d . . .
C2 C -0.3692(5) 0.18519(19) 0.2210(3) 0.0310(6) Uani 1 1 d . . .
C3 C -0.2636(6) 0.2748(2) 0.1986(3) 0.0344(6) Uani 1 1 d . . .
H3 H -0.3122 0.3271 0.2439 0.041 Uiso 1 1 calc R . .
C4 C -0.0886(6) 0.28815(19) 0.1109(3) 0.0337(6) Uani 1 1 d . . .
C5 C -0.0165(5) 0.2078(2) 0.0476(3) 0.0332(6) Uani 1 1 d . . .
H5 H 0.1031 0.2144 -0.0108 0.040 Uiso 1 1 calc R . .
C6 C -0.3950(6) 0.00784(18) 0.1518(3) 0.0303(6) Uani 1 1 d . . .
C7 C -0.5541(6) 0.1745(2) 0.3194(3) 0.0432(7) Uani 1 1 d . . .
H7A H -0.5609 0.2336 0.3643 0.065 Uiso 1 1 calc R . .
H7B H -0.4885 0.1248 0.3771 0.065 Uiso 1 1 calc R . .
H7C H -0.7306 0.1583 0.2796 0.065 Uiso 1 1 calc R . .
C8 C 0.0211(7) 0.3848(2) 0.0847(3) 0.0481(8) Uani 1 1 d . . .
H8A H -0.0733 0.4331 0.1247 0.072 Uiso 1 1 calc R . .
H8B H -0.0017 0.3958 -0.0044 0.072 Uiso 1 1 calc R . .
H8C H 0.2083 0.3873 0.1169 0.072 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 1.9337(18) 3 ?
Cu1 O1 1.9337(18) . ?
Cu1 N1 1.966(2) 3 ?
Cu1 N1 1.966(2) . ?
Cu1 O2 2.769(3) 3_455 ?
Cu1 O2 2.769(3) 1_655 ?
O1 C6 1.286(3) . ?
O2 C6 1.223(4) . ?
N1 C5 1.331(3) . ?
N1 C1 1.349(3) . ?
C1 C2 1.396(4) . ?
C1 C6 1.511(4) . ?
C2 C3 1.395(4) . ?
C2 C7 1.507(4) . ?
C3 C4 1.386(4) . ?
C3 H3 0.9300 . ?
C4 C5 1.387(4) . ?
C4 C8 1.502(4) . ?
C5 H5 0.9300 . ?
C7 H7A 0.9600 . ?
C7 H7B 0.9600 . ?
C7 H7C 0.9600 . ?
C8 H8A 0.9600 . ?
C8 H8B 0.9600 . ?
C8 H8C 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 180.00 3 . ?
O1 Cu1 N1 83.44(8) 3 3 ?
O1 Cu1 N1 96.56(8) . 3 ?
O1 Cu1 N1 96.56(8) 3 . ?
O1 Cu1 N1 83.44(8) . . ?
N1 Cu1 N1 180.00 3 . ?
O1 Cu1 O2 93.15(7) 3 3_455 ?
O1 Cu1 O2 86.85(7) . 3_455 ?
N1 Cu1 O2 88.71(8) 3 3_455 ?
N1 Cu1 O2 91.29(8) . 3_455 ?
O1 Cu1 O2 86.85(7) 3 1_655 ?
O1 Cu1 O2 93.15(7) . 1_655 ?
N1 Cu1 O2 91.29(8) 3 1_655 ?
N1 Cu1 O2 88.71(8) . 1_655 ?
O2 Cu1 O2 180.00 3_455 1_655 ?
C6 O1 Cu1 114.96(17) . . ?
C5 N1 C1 121.0(2) . . ?
C5 N1 Cu1 126.34(18) . . ?
C1 N1 Cu1 112.46(17) . . ?
N1 C1 C2 121.2(2) . . ?
N1 C1 C6 113.0(2) . . ?
C2 C1 C6 125.9(2) . . ?
C3 C2 C1 116.8(2) . . ?
C3 C2 C7 119.7(3) . . ?
C1 C2 C7 123.5(3) . . ?
C4 C3 C2 122.0(3) . . ?
C4 C3 H3 119.0 . . ?
C2 C3 H3 119.0 . . ?
C3 C4 C5 117.1(3) . . ?
C3 C4 C8 122.2(3) . . ?
C5 C4 C8 120.7(3) . . ?
N1 C5 C4 121.9(3) . . ?
N1 C5 H5 119.0 . . ?
C4 C5 H5 119.0 . . ?
O2 C6 O1 124.6(2) . . ?
O2 C6 C1 120.4(2) . . ?
O1 C6 C1 115.0(2) . . ?
C2 C7 H7A 109.5 . . ?
C2 C7 H7B 109.5 . . ?
H7A C7 H7B 109.5 . . ?
C2 C7 H7C 109.5 . . ?
H7A C7 H7C 109.5 . . ?
H7B C7 H7C 109.5 . . ?
C4 C8 H8A 109.5 . . ?
C4 C8 H8B 109.5 . . ?
H8A C8 H8B 109.5 . . ?
C4 C8 H8C 109.5 . . ?
H8A C8 H8C 109.5 . . ?
H8B C8 H8C 109.5 . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
C3 H3 O2 0.93 2.41 3.303(3) 160.8 2_455

_diffrn_measured_fraction_theta_max 0.958
_diffrn_reflns_theta_full        26.00
_diffrn_measured_fraction_theta_full 0.958
_refine_diff_density_max         0.460
_refine_diff_density_min         -0.287
_refine_diff_density_rms         0.087

#=======================================End

data_2
_database_code_depnum_ccdc_archive 'CCDC 727581'

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C16 H16 Cu3 N2 O12'
_chemical_formula_weight         618.93

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           triclinic
_symmetry_space_group_name_H-M   p-1

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

_cell_length_a                   7.3163(7)
_cell_length_b                   7.6838(7)
_cell_length_c                   17.9429(16)
_cell_angle_alpha                83.251(2)
_cell_angle_beta                 82.728(2)
_cell_angle_gamma                81.003(2)
_cell_volume                     983.34(16)
_cell_formula_units_Z            2
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    ?
_cell_measurement_theta_min      ?
_cell_measurement_theta_max      ?

_exptl_crystal_description       sheet-like
_exptl_crystal_colour            pale-green
_exptl_crystal_size_max          0.20
_exptl_crystal_size_mid          0.14
_exptl_crystal_size_min          0.06
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    2.090
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             618
_exptl_absorpt_coefficient_mu    3.287
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.5579
_exptl_absorpt_correction_T_max  0.8348
_exptl_absorpt_process_details   'SADABS (Bruker, 2002)'

_exptl_special_details           
;
?
;

_diffrn_ambient_temperature      293(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Bruker SMART CCD area detector'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            5824
_diffrn_reflns_av_R_equivalents  0.0187
_diffrn_reflns_av_sigmaI/netI    0.0362
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_theta_min         2.30
_diffrn_reflns_theta_max         26.00
_reflns_number_total             3610
_reflns_number_gt                3216
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'Bruker SMART (Bruker, 1998)'
_computing_cell_refinement       'Bruker SMART (Bruker, 1998)'
_computing_data_reduction        'Bruker SAINT + & SHELXTL (Bruker, 1998)'
_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)+(0.0559P)²+0.9974P] 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         3610
_refine_ls_number_parameters     309
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0416
_refine_ls_R_factor_gt           0.0371
_refine_ls_wR_factor_ref         0.0987
_refine_ls_wR_factor_gt          0.0954
_refine_ls_goodness_of_fit_ref   1.027
_refine_ls_restrained_S_all      1.027
_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 0.18324(6) 0.23761(6) 0.38549(2) 0.02892(14) Uani 1 1 d . . .
Cu2 Cu 0.0000 0.5000 0.5000 0.03158(17) Uani 1 2 d S . .
Cu3 Cu 0.19680(6) 0.86729(5) 0.03810(2) 0.02632(14) Uani 1 1 d . . .
Cu4 Cu 0.5000 0.5000 0.0000 0.03048(17) Uani 1 2 d S . .
O1W O 0.3633(5) 0.3764(5) 0.4501(2) 0.0683(11) Uani 1 1 d . . .
H1WA H 0.3932 0.4778 0.4350 0.069(17) Uiso 1 1 d R . .
H1WB H 0.4356 0.3222 0.4811 0.068(17) Uiso 1 1 d R . .
O2W O 0.2860(5) 0.3628(4) -0.07459(18) 0.0523(8) Uani 1 1 d . . .
H2WA H 0.2048 0.4533 -0.0803 0.10(2) Uiso 1 1 d R . .
H2WB H 0.2475 0.2888 -0.0398 0.09(2) Uiso 1 1 d R . .
O1 O -0.0362(4) 0.3064(4) 0.44967(14) 0.0348(6) Uani 1 1 d . . .
H1O H -0.0640 0.2184 0.4791 0.036(11) Uiso 1 1 d R . .
O2 O 0.2690(3) 0.6233(3) 0.04071(14) 0.0329(6) Uani 1 1 d . . .
H2O H 0.1983 0.5503 0.0611 0.043(13) Uiso 1 1 d R . .
O3 O 0.1068(4) 1.1195(3) 0.03505(14) 0.0358(6) Uani 1 1 d . . .
O4 O 0.0037(4) 1.3366(4) 0.10831(16) 0.0428(7) Uani 1 1 d . . .
O5 O 0.0072(4) 0.6503(4) 0.40222(13) 0.0396(7) Uani 1 1 d . . .
O6 O 0.1482(3) 0.4634(3) 0.31859(13) 0.0311(6) Uani 1 1 d . . .
O7 O 0.7665(4) 0.9962(4) -0.44077(14) 0.0434(7) Uani 1 1 d . . .
O8 O 0.5887(4) 1.2575(4) -0.43587(15) 0.0430(7) Uani 1 1 d . . .
O9 O 0.3256(4) 0.9199(3) -0.06177(14) 0.0397(7) Uani 1 1 d . . .
O10 O 0.5287(4) 0.6784(4) -0.08670(15) 0.0420(7) Uani 1 1 d . . .
N1 N 0.1022(4) 0.8749(4) 0.14750(15) 0.0245(6) Uani 1 1 d . . .
N2 N 0.6455(4) 0.8799(4) -0.30502(15) 0.0250(6) Uani 1 1 d . . .
C1 C 0.0267(4) 1.0399(4) 0.16487(19) 0.0237(7) Uani 1 1 d . . .
C2 C -0.0527(5) 1.0712(5) 0.23801(19) 0.0257(7) Uani 1 1 d . . .
C3 C -0.0398(5) 0.9272(5) 0.29266(19) 0.0273(7) Uani 1 1 d . . .
H3 H -0.0896 0.9432 0.3421 0.033 Uiso 1 1 calc R . .
C4 C 0.0449(4) 0.7614(5) 0.27562(18) 0.0238(7) Uani 1 1 d . . .
C5 C 0.1116(5) 0.7388(5) 0.20089(19) 0.0258(7) Uani 1 1 d . . .
H5 H 0.1637 0.6266 0.1879 0.031 Uiso 1 1 calc R . .
C6 C 0.0442(5) 1.1797(5) 0.0994(2) 0.0289(8) Uani 1 1 d . . .
C7 C -0.1486(6) 1.2490(5) 0.2582(2) 0.0354(9) Uani 1 1 d . . .
H7A H -0.2078 1.2381 0.3091 0.053 Uiso 1 1 calc R . .
H7B H -0.2407 1.2935 0.2244 0.053 Uiso 1 1 calc R . .
H7C H -0.0588 1.3293 0.2540 0.053 Uiso 1 1 calc R . .
C8 C 0.0674(5) 0.6117(5) 0.33751(19) 0.0260(7) Uani 1 1 d . . .
C9 C 0.5843(5) 1.0538(5) -0.32584(19) 0.0250(7) Uani 1 1 d . . .
C10 C 0.4784(5) 1.1641(5) -0.2758(2) 0.0274(7) Uani 1 1 d . . .
C11 C 0.4362(5) 1.0886(5) -0.2022(2) 0.0274(7) Uani 1 1 d . . .
H11 H 0.3664 1.1583 -0.1667 0.033 Uiso 1 1 calc R . .
C12 C 0.4959(4) 0.9131(5) -0.18120(18) 0.0247(7) Uani 1 1 d . . .
C13 C 0.6033(5) 0.8116(5) -0.23451(18) 0.0252(7) Uani 1 1 d . . .
H13 H 0.6465 0.6934 -0.2205 0.030 Uiso 1 1 calc R . .
C14 C 0.6497(5) 1.1096(5) -0.4073(2) 0.0308(8) Uani 1 1 d . . .
C15 C 0.4113(6) 1.3570(5) -0.2948(2) 0.0435(10) Uani 1 1 d . . .
H15A H 0.3476 1.3720 -0.3392 0.065 Uiso 1 1 calc R . .
H15B H 0.5158 1.4212 -0.3039 0.065 Uiso 1 1 calc R . .
H15C H 0.3276 1.4013 -0.2534 0.065 Uiso 1 1 calc R . .
C16 C 0.4463(5) 0.8295(5) -0.10269(19) 0.0263(7) 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
Cu1 O1 1.896(3) . ?
Cu1 O7 1.953(3) 2_665 ?
Cu1 N2 1.991(3) 2_665 ?
Cu1 O6 1.992(2) . ?
Cu1 O1W 2.309(3) . ?
Cu2 O1 1.897(3) . ?
Cu2 O1 1.897(3) 2_566 ?
Cu2 O5 1.983(2) . ?
Cu2 O5 1.983(2) 2_566 ?
Cu3 O2 1.864(2) . ?
Cu3 O3 1.944(3) . ?
Cu3 O9 1.945(2) . ?
Cu3 N1 2.002(3) . ?
Cu4 O2 1.907(2) 2_665 ?
Cu4 O2 1.907(2) . ?
Cu4 O10 1.962(2) . ?
Cu4 O10 1.962(2) 2_665 ?
Cu4 O2W 2.595(3) . ?
O1W H1WA 0.8467 . ?
O1W H1WB 0.8455 . ?
O2W H2WA 0.8464 . ?
O2W H2WB 0.8449 . ?
O1 H1O 0.8422 . ?
O2 H2O 0.8429 . ?
O3 C6 1.296(4) . ?
O4 C6 1.220(4) . ?
O5 C8 1.241(4) . ?
O6 C8 1.261(4) . ?
O7 C14 1.269(5) . ?
O7 Cu1 1.953(3) 2_665 ?
O8 C14 1.231(5) . ?
O9 C16 1.251(4) . ?
O10 C16 1.241(4) . ?
N1 C5 1.332(4) . ?
N1 C1 1.357(4) . ?
N2 C13 1.329(4) . ?
N2 C9 1.365(4) . ?
N2 Cu1 1.991(3) 2_665 ?
C1 C2 1.398(5) . ?
C1 C6 1.503(5) . ?
C2 C3 1.389(5) . ?
C2 C7 1.497(5) . ?
C3 C4 1.377(5) . ?
C3 H3 0.9300 . ?
C4 C5 1.389(5) . ?
C4 C8 1.507(5) . ?
C5 H5 0.9300 . ?
C7 H7A 0.9600 . ?
C7 H7B 0.9600 . ?
C7 H7C 0.9600 . ?
C9 C10 1.387(5) . ?
C9 C14 1.513(5) . ?
C10 C11 1.395(5) . ?
C10 C15 1.500(5) . ?
C11 C12 1.375(5) . ?
C11 H11 0.9300 . ?
C12 C13 1.390(5) . ?
C12 C16 1.503(4) . ?
C13 H13 0.9300 . ?
C15 H15A 0.9600 . ?
C15 H15B 0.9600 . ?
C15 H15C 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 O7 93.80(12) . 2_665 ?
O1 Cu1 N2 160.48(12) . 2_665 ?
O7 Cu1 N2 82.06(11) 2_665 2_665 ?
O1 Cu1 O6 92.18(11) . . ?
O7 Cu1 O6 173.30(11) 2_665 . ?
N2 Cu1 O6 91.30(11) 2_665 . ?
O1 Cu1 O1W 92.67(14) . . ?
O7 Cu1 O1W 96.27(12) 2_665 . ?
N2 Cu1 O1W 106.72(14) 2_665 . ?
O6 Cu1 O1W 86.45(11) . . ?
O1 Cu2 O1 180.00(12) . 2_566 ?
O1 Cu2 O5 89.55(11) . . ?
O1 Cu2 O5 90.45(11) 2_566 . ?
O1 Cu2 O5 90.45(11) . 2_566 ?
O1 Cu2 O5 89.55(11) 2_566 2_566 ?
O5 Cu2 O5 180.000(1) . 2_566 ?
O2 Cu3 O3 176.67(12) . . ?
O2 Cu3 O9 94.82(11) . . ?
O3 Cu3 O9 86.40(11) . . ?
O2 Cu3 N1 97.40(11) . . ?
O3 Cu3 N1 82.11(11) . . ?
O9 Cu3 N1 162.29(12) . . ?
O2 Cu4 O2 180.0 2_665 . ?
O2 Cu4 O10 86.53(10) 2_665 . ?
O2 Cu4 O10 93.47(10) . . ?
O2 Cu4 O10 93.47(10) 2_665 2_665 ?
O2 Cu4 O10 86.53(10) . 2_665 ?
O10 Cu4 O10 180.00(11) . 2_665 ?
O2 Cu4 O2W 97.18(11) 2_665 . ?
O2 Cu4 O2W 82.82(11) . . ?
O10 Cu4 O2W 87.89(12) . . ?
O10 Cu4 O2W 92.11(12) 2_665 . ?
Cu1 O1W H1WA 122.9 . . ?
Cu1 O1W H1WB 123.7 . . ?
H1WA O1W H1WB 110.3 . . ?
Cu4 O2W H2WA 97.5 . . ?
Cu4 O2W H2WB 98.6 . . ?
H2WA O2W H2WB 110.9 . . ?
Cu1 O1 Cu2 108.84(13) . . ?
Cu1 O1 H1O 109.6 . . ?
Cu2 O1 H1O 113.7 . . ?
Cu3 O2 Cu4 127.79(14) . . ?
Cu3 O2 H2O 122.3 . . ?
Cu4 O2 H2O 109.9 . . ?
C6 O3 Cu3 116.3(2) . . ?
C8 O5 Cu2 130.3(2) . . ?
C8 O6 Cu1 126.7(2) . . ?
C14 O7 Cu1 116.3(2) . 2_665 ?
C16 O9 Cu3 132.5(2) . . ?
C16 O10 Cu4 133.4(2) . . ?
C5 N1 C1 120.6(3) . . ?
C5 N1 Cu3 126.4(2) . . ?
C1 N1 Cu3 112.9(2) . . ?
C13 N2 C9 119.7(3) . . ?
C13 N2 Cu1 126.8(2) . 2_665 ?
C9 N2 Cu1 113.1(2) . 2_665 ?
N1 C1 C2 121.4(3) . . ?
N1 C1 C6 113.4(3) . . ?
C2 C1 C6 125.2(3) . . ?
C3 C2 C1 116.6(3) . . ?
C3 C2 C7 120.4(3) . . ?
C1 C2 C7 122.9(3) . . ?
C4 C3 C2 121.8(3) . . ?
C4 C3 H3 119.1 . . ?
C2 C3 H3 119.1 . . ?
C3 C4 C5 118.2(3) . . ?
C3 C4 C8 120.1(3) . . ?
C5 C4 C8 121.7(3) . . ?
N1 C5 C4 121.2(3) . . ?
N1 C5 H5 119.4 . . ?
C4 C5 H5 119.4 . . ?
O4 C6 O3 124.3(3) . . ?
O4 C6 C1 120.9(3) . . ?
O3 C6 C1 114.8(3) . . ?
C2 C7 H7A 109.5 . . ?
C2 C7 H7B 109.5 . . ?
H7A C7 H7B 109.5 . . ?
C2 C7 H7C 109.5 . . ?
H7A C7 H7C 109.5 . . ?
H7B C7 H7C 109.5 . . ?
O5 C8 O6 127.3(3) . . ?
O5 C8 C4 115.5(3) . . ?
O6 C8 C4 117.2(3) . . ?
N2 C9 C10 122.3(3) . . ?
N2 C9 C14 112.4(3) . . ?
C10 C9 C14 125.3(3) . . ?
C9 C10 C11 116.7(3) . . ?
C9 C10 C15 124.7(3) . . ?
C11 C10 C15 118.6(3) . . ?
C12 C11 C10 121.2(3) . . ?
C12 C11 H11 119.4 . . ?
C10 C11 H11 119.4 . . ?
C11 C12 C13 118.7(3) . . ?
C11 C12 C16 121.5(3) . . ?
C13 C12 C16 119.8(3) . . ?
N2 C13 C12 121.4(3) . . ?
N2 C13 H13 119.3 . . ?
C12 C13 H13 119.3 . . ?
O8 C14 O7 125.2(3) . . ?
O8 C14 C9 119.2(3) . . ?
O7 C14 C9 115.6(3) . . ?
C10 C15 H15A 109.5 . . ?
C10 C15 H15B 109.5 . . ?
H15A C15 H15B 109.5 . . ?
C10 C15 H15C 109.5 . . ?
H15A C15 H15C 109.5 . . ?
H15B C15 H15C 109.5 . . ?
O10 C16 O9 128.0(3) . . ?
O10 C16 C12 116.0(3) . . ?
O9 C16 C12 116.1(3) . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
O1W H1WA O8 0.85 2.06 2.867(4) 158.9 2_675
O1W H1WB O8 0.85 1.95 2.772(4) 164.7 1_546
O2W H2WA O4 0.85 2.10 2.943(5) 171.9 2_575
O2W H2WB O3 0.84 2.05 2.887(4) 168.9 1_545
O1 H1O O7 0.84 2.48 3.299(4) 164.3 1_446
O2 H2O O4 0.84 2.35 3.195(4) 175.2 1_545

_diffrn_measured_fraction_theta_max 0.938
_diffrn_reflns_theta_full        26.00
_diffrn_measured_fraction_theta_full 0.938
_refine_diff_density_max         0.817
_refine_diff_density_min         -0.403
_refine_diff_density_rms         0.107

#=======================================End

data_2a
_database_code_depnum_ccdc_archive 'CCDC 727582'

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C16 H14 Cu2 N2 O10'
_chemical_formula_weight         521.37

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           triclinic
_symmetry_space_group_name_H-M   P-1

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

_cell_length_a                   7.6284(11)
_cell_length_b                   11.058(2)
_cell_length_c                   11.284(5)
_cell_angle_alpha                102.71(3)
_cell_angle_beta                 105.21(2)
_cell_angle_gamma                106.870(16)
_cell_volume                     832.6(4)
_cell_formula_units_Z            2
_cell_measurement_temperature    123(2)
_cell_measurement_reflns_used    ?
_cell_measurement_theta_min      ?
_cell_measurement_theta_max      ?

_exptl_crystal_description       sheet-like
_exptl_crystal_colour            pale-green
_exptl_crystal_size_max          0.18
_exptl_crystal_size_mid          0.11
_exptl_crystal_size_min          0.07
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    2.080
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             524
_exptl_absorpt_coefficient_mu    2.622
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.6496
_exptl_absorpt_correction_T_max  0.8377
_exptl_absorpt_process_details   'SADABS (Bruker, 2002)'

_exptl_special_details           
;
?
;

_diffrn_ambient_temperature      123(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Bruker SMART CCD area detector'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            5997
_diffrn_reflns_av_R_equivalents  0.0457
_diffrn_reflns_av_sigmaI/netI    0.1143
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_theta_min         2.92
_diffrn_reflns_theta_max         25.99
_reflns_number_total             3076
_reflns_number_gt                1848
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'Bruker SMART (Bruker, 1998)'
_computing_cell_refinement       'Bruker SMART (Bruker, 1998)'
_computing_data_reduction        'Bruker SAINT + & SHELXTL (Bruker, 1998)'
_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)+(0.0919P)²+0.6856P] 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         3076
_refine_ls_number_parameters     273
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1001
_refine_ls_R_factor_gt           0.0563
_refine_ls_wR_factor_ref         0.1810
_refine_ls_wR_factor_gt          0.1593
_refine_ls_goodness_of_fit_ref   1.079
_refine_ls_restrained_S_all      1.079
_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 0.04544(14) 0.65614(9) 0.73873(9) 0.0219(3) Uani 1 1 d . . .
Cu2 Cu 0.52307(14) 1.43359(9) 1.26605(9) 0.0218(3) Uani 1 1 d . . .
O1W O -0.1022(8) 0.4681(5) 0.6512(5) 0.0277(13) Uani 1 1 d . . .
H1WA H -0.1620 0.4436 0.5699 0.033 Uiso 1 1 d R . .
H1WB H -0.1806 0.4383 0.6885 0.033 Uiso 1 1 d R . .
O2W O 0.3294(8) 1.3367(5) 1.3295(5) 0.0243(13) Uani 1 1 d . . .
H2WA H 0.3586 1.3557 1.4112 0.029 Uiso 1 1 d R . .
H2WB H 0.2979 1.2531 1.2975 0.029 Uiso 1 1 d R . .
O1 O 0.1746(8) 0.6623(5) 0.6116(5) 0.0295(14) Uani 1 1 d . . .
O2 O 0.3540(9) 0.8083(6) 0.5387(6) 0.0386(16) Uani 1 1 d . . .
O3 O 0.4521(8) 1.2810(5) 1.1155(5) 0.0209(12) Uani 1 1 d . . .
O4 O 0.2480(9) 1.1114(5) 1.1521(6) 0.0304(14) Uani 1 1 d . . .
O5 O 0.8658(9) 1.7909(5) 1.5089(6) 0.0348(15) Uani 1 1 d . . .
O6 O 0.6356(8) 1.5886(5) 1.4187(5) 0.0237(13) Uani 1 1 d . . .
O7 O 0.7279(8) 1.4701(5) 0.8342(5) 0.0244(13) Uani 1 1 d . . .
O8 O 0.9992(8) 1.6547(5) 0.8993(5) 0.0197(12) Uani 1 1 d . . .
N1 N 0.1928(9) 0.8506(6) 0.8064(6) 0.0194(15) Uani 1 1 d . . .
N2 N 0.7041(9) 1.5507(6) 1.2029(6) 0.0211(15) Uani 1 1 d . . .
C1 C 0.2925(11) 0.8959(7) 0.7326(7) 0.0183(17) Uani 1 1 d . . .
C2 C 0.4088(11) 1.0299(8) 0.7621(8) 0.0262(19) Uani 1 1 d . . .
C3 C 0.4186(11) 1.1151(8) 0.8802(7) 0.0202(17) Uani 1 1 d . . .
H3 H 0.4947 1.2076 0.9065 0.024 Uiso 1 1 calc R . .
C4 C 0.3216(12) 1.0683(8) 0.9578(7) 0.0237(18) Uani 1 1 d . . .
C5 C 0.2072(12) 0.9352(8) 0.9168(7) 0.0225(18) Uani 1 1 d . . .
H5 H 0.1364 0.9021 0.9681 0.027 Uiso 1 1 calc R . .
C6 C 0.2760(12) 0.7846(8) 0.6168(8) 0.0241(18) Uani 1 1 d . . .
C7 C 0.5079(12) 1.0862(8) 0.6778(7) 0.026(2) Uani 1 1 d . . .
H7A H 0.5911 1.0378 0.6577 0.040 Uiso 1 1 calc R . .
H7B H 0.5885 1.1808 0.7233 0.040 Uiso 1 1 calc R . .
H7C H 0.4093 1.0771 0.5972 0.040 Uiso 1 1 calc R . .
C8 C 0.3373(11) 1.1603(7) 1.0839(7) 0.0170(17) Uani 1 1 d . . .
C9 C 0.8058(10) 1.6740(7) 1.2901(7) 0.0167(16) Uani 1 1 d . . .
C10 C 0.9306(11) 1.7752(7) 1.2618(7) 0.0185(17) Uani 1 1 d . . .
C11 C 0.9497(11) 1.7399(8) 1.1395(8) 0.0250(19) Uani 1 1 d . . .
H11 H 1.0334 1.8055 1.1165 0.030 Uiso 1 1 calc R . .
C12 C 0.8491(11) 1.6113(8) 1.0511(7) 0.0185(17) Uani 1 1 d . . .
C13 C 0.7233(11) 1.5182(8) 1.0874(7) 0.0197(17) Uani 1 1 d . . .
H13 H 0.6503 1.4304 1.0285 0.024 Uiso 1 1 calc R . .
C14 C 0.7722(12) 1.6912(7) 1.4183(8) 0.0226(18) Uani 1 1 d . . .
C15 C 1.0325(11) 1.9184(7) 1.3487(7) 0.0228(18) Uani 1 1 d . . .
H15A H 0.9386 1.9496 1.3781 0.034 Uiso 1 1 calc R . .
H15B H 1.0866 1.9739 1.3004 0.034 Uiso 1 1 calc R . .
H15C H 1.1386 1.9248 1.4239 0.034 Uiso 1 1 calc R . .
C16 C 0.8582(11) 1.5753(7) 0.9171(8) 0.0191(17) 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
Cu1 O1W 1.929(5) . ?
Cu1 O8 1.937(5) 1_445 ?
Cu1 O1 1.944(6) . ?
Cu1 N1 1.973(6) . ?
Cu1 O2W 2.789(5) 2_577 ?
Cu2 O6 1.927(5) . ?
Cu2 O3 1.937(5) . ?
Cu2 O2W 1.954(6) . ?
Cu2 N2 1.994(7) . ?
Cu2 O7 2.580(5) 2_687 ?
O1W H1WA 0.8500 . ?
O1W H1WB 0.8499 . ?
O2W H2WA 0.8500 . ?
O2W H2WB 0.8500 . ?
O1 C6 1.329(10) . ?
O2 C6 1.219(10) . ?
O3 C8 1.275(9) . ?
O4 C8 1.262(10) . ?
O5 C14 1.198(9) . ?
O6 C14 1.301(10) . ?
O7 C16 1.256(9) . ?
O8 C16 1.269(9) . ?
O8 Cu1 1.937(5) 1_665 ?
N1 C5 1.340(10) . ?
N1 C1 1.348(10) . ?
N2 C13 1.332(10) . ?
N2 C9 1.350(10) . ?
C1 C2 1.400(11) . ?
C1 C6 1.534(11) . ?
C2 C3 1.423(11) . ?
C2 C7 1.493(11) . ?
C3 C4 1.378(12) . ?
C3 H3 0.9500 . ?
C4 C5 1.374(11) . ?
C4 C8 1.509(11) . ?
C5 H5 0.9500 . ?
C7 H7A 0.9800 . ?
C7 H7B 0.9800 . ?
C7 H7C 0.9800 . ?
C9 C10 1.400(11) . ?
C9 C14 1.516(11) . ?
C10 C11 1.406(11) . ?
C10 C15 1.509(10) . ?
C11 C12 1.396(11) . ?
C11 H11 0.9500 . ?
C12 C13 1.402(11) . ?
C12 C16 1.502(10) . ?
C13 H13 0.9500 . ?
C15 H15A 0.9800 . ?
C15 H15B 0.9800 . ?
C15 H15C 0.9800 . ?

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
O1W Cu1 O8 94.7(2) . 1_445 ?
O1W Cu1 O1 90.4(2) . . ?
O8 Cu1 O1 161.4(2) 1_445 . ?
O1W Cu1 N1 172.8(3) . . ?
O8 Cu1 N1 92.1(2) 1_445 . ?
O1 Cu1 N1 83.8(3) . . ?
O1W Cu1 O2W 81.3(2) . 2_577 ?
O8 Cu1 O2W 80.8(2) 1_445 2_577 ?
O1 Cu1 O2W 117.6(2) . 2_577 ?
N1 Cu1 O2W 97.6(2) . 2_577 ?
O6 Cu2 O3 171.0(2) . . ?
O6 Cu2 O2W 93.4(2) . . ?
O3 Cu2 O2W 92.9(2) . . ?
O6 Cu2 N2 82.8(3) . . ?
O3 Cu2 N2 91.6(2) . . ?
O2W Cu2 N2 172.3(2) . . ?
O6 Cu2 O7 89.3(2) . 2_687 ?
O3 Cu2 O7 97.40(19) . 2_687 ?
O2W Cu2 O7 87.4(2) . 2_687 ?
N2 Cu2 O7 85.8(2) . 2_687 ?
Cu1 O1W H1WA 117.3 . . ?
Cu1 O1W H1WB 110.1 . . ?
H1WA O1W H1WB 110.2 . . ?
Cu2 O2W H2WA 117.4 . . ?
Cu2 O2W H2WB 110.5 . . ?
H2WA O2W H2WB 108.0 . . ?
C6 O1 Cu1 114.5(5) . . ?
C8 O3 Cu2 131.1(5) . . ?
C14 O6 Cu2 116.8(5) . . ?
C16 O8 Cu1 128.9(5) . 1_665 ?
C5 N1 C1 119.8(7) . . ?
C5 N1 Cu1 126.6(6) . . ?
C1 N1 Cu1 113.5(5) . . ?
C13 N2 C9 121.5(7) . . ?
C13 N2 Cu2 126.2(5) . . ?
C9 N2 Cu2 112.3(5) . . ?
N1 C1 C2 123.7(7) . . ?
N1 C1 C6 113.3(6) . . ?
C2 C1 C6 122.9(7) . . ?
C1 C2 C3 114.0(8) . . ?
C1 C2 C7 125.5(8) . . ?
C3 C2 C7 120.4(7) . . ?
C4 C3 C2 122.3(7) . . ?
C4 C3 H3 118.8 . . ?
C2 C3 H3 118.8 . . ?
C5 C4 C3 118.3(8) . . ?
C5 C4 C8 120.3(8) . . ?
C3 C4 C8 121.4(7) . . ?
N1 C5 C4 121.7(8) . . ?
N1 C5 H5 119.1 . . ?
C4 C5 H5 119.1 . . ?
O2 C6 O1 123.7(7) . . ?
O2 C6 C1 121.9(7) . . ?
O1 C6 C1 114.4(7) . . ?
C2 C7 H7A 109.5 . . ?
C2 C7 H7B 109.5 . . ?
H7A C7 H7B 109.5 . . ?
C2 C7 H7C 109.5 . . ?
H7A C7 H7C 109.5 . . ?
H7B C7 H7C 109.5 . . ?
O4 C8 O3 125.7(7) . . ?
O4 C8 C4 118.6(7) . . ?
O3 C8 C4 115.6(7) . . ?
N2 C9 C10 121.7(7) . . ?
N2 C9 C14 114.2(7) . . ?
C10 C9 C14 124.1(7) . . ?
C9 C10 C11 116.3(7) . . ?
C9 C10 C15 124.6(7) . . ?
C11 C10 C15 119.0(7) . . ?
C12 C11 C10 121.8(8) . . ?
C12 C11 H11 119.1 . . ?
C10 C11 H11 119.1 . . ?
C11 C12 C13 117.4(7) . . ?
C11 C12 C16 122.1(7) . . ?
C13 C12 C16 120.3(7) . . ?
N2 C13 C12 121.2(7) . . ?
N2 C13 H13 119.4 . . ?
C12 C13 H13 119.4 . . ?
O5 C14 O6 124.8(8) . . ?
O5 C14 C9 121.6(8) . . ?
O6 C14 C9 113.6(6) . . ?
C10 C15 H15A 109.5 . . ?
C10 C15 H15B 109.5 . . ?
H15A C15 H15B 109.5 . . ?
C10 C15 H15C 109.5 . . ?
H15A C15 H15C 109.5 . . ?
H15B C15 H15C 109.5 . . ?
O7 C16 O8 126.3(7) . . ?
O7 C16 C12 117.5(7) . . ?
O8 C16 C12 116.2(7) . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
O1W H1WA O1 0.85 2.09 2.824(8) 144.9 2_566
O1W H1WB O7 0.85 1.95 2.710(8) 148.3 1_445
O2W H2WA O6 0.85 1.87 2.695(7) 164.5 2_688
O2W H2WB O4 0.85 1.87 2.618(8) 146.5 .

_diffrn_measured_fraction_theta_max 0.939
_diffrn_reflns_theta_full        25.99
_diffrn_measured_fraction_theta_full 0.939
_refine_diff_density_max         1.492
_refine_diff_density_min         -0.633
_refine_diff_density_rms         0.157

#==========================================End

data_4
_database_code_depnum_ccdc_archive 'CCDC 727583'

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C16 H14 Cu4 N2 O22'
_chemical_formula_weight         840.45

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'
Cu Cu 0.3201 1.2651 '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                   7.0602(7)
_cell_length_b                   9.5054(10)
_cell_length_c                   10.8957(11)
_cell_angle_alpha                101.345(2)
_cell_angle_beta                 107.878(2)
_cell_angle_gamma                111.340(2)
_cell_volume                     607.69(11)
_cell_formula_units_Z            1
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    ?
_cell_measurement_theta_min      ?
_cell_measurement_theta_max      ?

_exptl_crystal_description       block
_exptl_crystal_colour            green
_exptl_crystal_size_max          0.26
_exptl_crystal_size_mid          0.17
_exptl_crystal_size_min          0.10
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    2.297
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             416
_exptl_absorpt_coefficient_mu    3.565
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.4575
_exptl_absorpt_correction_T_max  0.7169
_exptl_absorpt_process_details   'SADABS (Bruker, 2002)'

_exptl_special_details           
;
?
;

_diffrn_ambient_temperature      293(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Bruker SMART CCD area detector'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            3295
_diffrn_reflns_av_R_equivalents  0.0143
_diffrn_reflns_av_sigmaI/netI    0.0314
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_theta_min         2.45
_diffrn_reflns_theta_max         26.00
_reflns_number_total             2332
_reflns_number_gt                2179
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'Bruker SMART (Bruker, 1998)'
_computing_cell_refinement       'Bruker SMART (Bruker, 1998)'
_computing_data_reduction        'Bruker SAINT + & SHELXTL (Bruker, 1998)'
_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)+(0.0454P)²+0.5933P] 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         2332
_refine_ls_number_parameters     212
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0323
_refine_ls_R_factor_gt           0.0304
_refine_ls_wR_factor_ref         0.0843
_refine_ls_wR_factor_gt          0.0827
_refine_ls_goodness_of_fit_ref   1.089
_refine_ls_restrained_S_all      1.089
_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
Cu1 Cu 0.68780(5) 1.40354(4) 0.09786(3) 0.01899(13) Uani 1 1 d . . .
Cu2 Cu -0.24071(5) 0.90212(4) -0.52403(3) 0.02244(13) Uani 1 1 d . . .
N1 N 0.3806(4) 1.2751(3) -0.0224(2) 0.0187(5) Uani 1 1 d . . .
O1 O 0.7101(3) 1.3603(2) -0.0881(2) 0.0223(4) Uani 1 1 d . . .
O2 O 0.5106(3) 1.2217(3) -0.30904(19) 0.0234(5) Uani 1 1 d . . .
O3 O -0.3901(3) 0.9021(3) -0.4056(2) 0.0262(5) Uani 1 1 d . . .
O4 O -0.4277(3) 0.9496(3) -0.2109(2) 0.0294(5) Uani 1 1 d . . .
O5 O 0.2275(4) 1.3303(3) 0.2512(2) 0.0273(5) Uani 1 1 d . . .
O6 O 0.5514(3) 1.4366(3) 0.2325(2) 0.0236(4) Uani 1 1 d . . .
O7 O 0.0509(3) 1.0408(3) -0.3779(2) 0.0283(5) Uani 1 1 d . . .
O1W O 0.7652(4) 1.2174(3) 0.1514(3) 0.0327(5) Uani 1 1 d . . .
H1WA H 0.6754 1.1639 0.1810 0.055(14) Uiso 1 1 d R . .
H1WB H 0.8978 1.2398 0.2021 0.042(12) Uiso 1 1 d R . .
O2W O 0.9801(3) 1.5745(3) 0.2005(2) 0.0284(5) Uani 1 1 d . . .
H2WA H 1.0489 1.6085 0.2876 0.034 Uiso 1 1 d R . .
H2WB H 1.0757 1.5883 0.1662 0.034 Uiso 1 1 d R . .
O3W O -0.2198(4) 0.6684(3) -0.5044(2) 0.0302(5) Uani 1 1 d . . .
H3WA H -0.3048 0.5871 -0.5773 0.049(12) Uiso 1 1 d R . .
H3WB H -0.2508 0.6504 -0.4381 0.052(13) Uiso 1 1 d R . .
O4W O 1.1657(8) 1.6514(7) 0.4666(5) 0.0354(11) Uani 0.50 1 d P . .
O4W' O 1.1603(9) 1.7568(10) 0.4572(6) 0.0548(17) Uani 0.50 1 d P . .
C1 C 0.3242(5) 1.2086(3) -0.1562(3) 0.0175(6) Uani 1 1 d . . .
C2 C 0.1010(5) 1.1044(3) -0.2465(3) 0.0186(6) Uani 1 1 d . . .
C3 C -0.0610(4) 1.0741(3) -0.1913(3) 0.0175(6) Uani 1 1 d . . .
C4 C 0.0080(4) 1.1485(3) -0.0513(3) 0.0175(5) Uani 1 1 d . . .
H4 H -0.0964 1.1303 -0.0135 0.021 Uiso 1 1 calc R . .
C5 C 0.2318(5) 1.2498(3) 0.0317(3) 0.0174(5) Uani 1 1 d . . .
C6 C 0.5254(5) 1.2645(3) -0.1890(3) 0.0190(6) Uani 1 1 d . . .
C7 C -0.3104(5) 0.9673(3) -0.2746(3) 0.0196(6) Uani 1 1 d . . .
C8 C 0.3401(5) 1.3454(3) 0.1847(3) 0.0195(6) Uani 1 1 d . . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Cu1 O2W 1.892(2) . ?
Cu1 N1 1.900(2) . ?
Cu1 O6 2.021(2) . ?
Cu1 O1 2.053(2) . ?
Cu1 O1W 2.164(2) . ?
Cu2 O3 1.900(2) . ?
Cu2 O7 1.923(2) . ?
Cu2 O2 1.9294(19) 2_574 ?
Cu2 O7 1.952(2) 2_574 ?
Cu2 O3W 2.325(2) . ?
Cu2 Cu2 3.0348(7) 2_574 ?
N1 C5 1.327(4) . ?
N1 C1 1.335(4) . ?
O1 C6 1.264(3) . ?
O2 C6 1.251(3) . ?
O2 Cu2 1.9294(19) 2_574 ?
O3 C7 1.282(3) . ?
O4 C7 1.222(3) . ?
O5 C8 1.220(4) . ?
O6 C8 1.285(4) . ?
O7 C2 1.316(3) . ?
O7 Cu2 1.952(2) 2_574 ?
O1W H1WA 0.8485 . ?
O1W H1WB 0.8469 . ?
O2W H2WA 0.8500 . ?
O2W H2WB 0.8500 . ?
O3W H3WA 0.8467 . ?
O3W H3WB 0.8476 . ?
O4W O4W' 1.040(8) . ?
C1 C2 1.400(4) . ?
C1 C6 1.504(4) . ?
C2 C3 1.416(4) . ?
C3 C4 1.390(4) . ?
C3 C7 1.519(4) . ?
C4 C5 1.383(4) . ?
C4 H4 0.9300 . ?
C5 C8 1.519(4) . ?

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
O2W Cu1 N1 164.54(10) . . ?
O2W Cu1 O6 99.63(9) . . ?
N1 Cu1 O6 80.61(9) . . ?
O2W Cu1 O1 96.30(9) . . ?
N1 Cu1 O1 79.92(9) . . ?
O6 Cu1 O1 157.78(9) . . ?
O2W Cu1 O1W 96.23(10) . . ?
N1 Cu1 O1W 99.10(10) . . ?
O6 Cu1 O1W 96.67(9) . . ?
O1 Cu1 O1W 96.89(9) . . ?
O3 Cu2 O7 93.84(9) . . ?
O3 Cu2 O2 95.06(9) . 2_574 ?
O7 Cu2 O2 170.01(9) . 2_574 ?
O3 Cu2 O7 165.90(9) . 2_574 ?
O7 Cu2 O7 76.92(9) . 2_574 ?
O2 Cu2 O7 93.48(8) 2_574 2_574 ?
O3 Cu2 O3W 92.03(9) . . ?
O7 Cu2 O3W 93.29(9) . . ?
O2 Cu2 O3W 90.90(9) 2_574 . ?
O7 Cu2 O3W 99.03(9) 2_574 . ?
O3 Cu2 Cu2 131.79(6) . 2_574 ?
O7 Cu2 Cu2 38.80(6) . 2_574 ?
O2 Cu2 Cu2 131.54(6) 2_574 2_574 ?
O7 Cu2 Cu2 38.12(6) 2_574 2_574 ?
O3W Cu2 Cu2 97.89(6) . 2_574 ?
C5 N1 C1 122.8(2) . . ?
C5 N1 Cu1 118.25(19) . . ?
C1 N1 Cu1 118.88(19) . . ?
C6 O1 Cu1 113.69(18) . . ?
C6 O2 Cu2 127.18(18) . 2_574 ?
C7 O3 Cu2 130.07(19) . . ?
C8 O6 Cu1 114.29(18) . . ?
C2 O7 Cu2 127.59(18) . . ?
C2 O7 Cu2 128.25(18) . 2_574 ?
Cu2 O7 Cu2 103.08(9) . 2_574 ?
Cu1 O1W H1WA 111.2 . . ?
Cu1 O1W H1WB 120.3 . . ?
H1WA O1W H1WB 110.0 . . ?
Cu1 O2W H2WA 124.8 . . ?
Cu1 O2W H2WB 119.3 . . ?
H2WA O2W H2WB 108.4 . . ?
Cu2 O3W H3WA 113.3 . . ?
Cu2 O3W H3WB 109.0 . . ?
H3WA O3W H3WB 110.1 . . ?
N1 C1 C2 120.5(3) . . ?
N1 C1 C6 111.1(2) . . ?
C2 C1 C6 128.4(3) . . ?
O7 C2 C1 119.0(2) . . ?
O7 C2 C3 123.1(3) . . ?
C1 C2 C3 117.9(2) . . ?
C4 C3 C2 118.8(2) . . ?
C4 C3 C7 116.3(2) . . ?
C2 C3 C7 124.8(2) . . ?
C5 C4 C3 120.1(2) . . ?
C5 C4 H4 120.0 . . ?
C3 C4 H4 120.0 . . ?
N1 C5 C4 119.9(2) . . ?
N1 C5 C8 111.8(2) . . ?
C4 C5 C8 128.3(3) . . ?
O2 C6 O1 121.9(3) . . ?
O2 C6 C1 122.1(2) . . ?
O1 C6 C1 116.0(2) . . ?
O4 C7 O3 122.7(3) . . ?
O4 C7 C3 116.8(2) . . ?
O3 C7 C3 120.4(2) . . ?
O5 C8 O6 125.8(3) . . ?
O5 C8 C5 120.0(3) . . ?
O6 C8 C5 114.1(2) . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
O1W H1WA O4 0.85 1.86 2.687(3) 166.0 2_575
O1W H1WB O5 0.85 2.01 2.792(3) 153.2 1_655
O2W H2WB O1 0.85 1.91 2.762(3) 174.0 2_785
O3W H3WA O6 0.85 1.96 2.787(3) 163.6 1_444
O3W H3WB O5 0.85 1.96 2.773(3) 161.3 2_575

_diffrn_measured_fraction_theta_max 0.975
_diffrn_reflns_theta_full        26.00
_diffrn_measured_fraction_theta_full 0.975
_refine_diff_density_max         0.428
_refine_diff_density_min         -0.542
_refine_diff_density_rms         0.121

#========================================End

data_3
_database_code_depnum_ccdc_archive 'CCDC 727584'

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C8 H3 Cu2 N O7'
_chemical_formula_weight         352.19

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           orthorhombic
_symmetry_space_group_name_H-M   pnna

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

_cell_length_a                   8.909(2)
_cell_length_b                   12.330(3)
_cell_length_c                   17.476(4)
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_volume                     1919.7(8)
_cell_formula_units_Z            8
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    ?
_cell_measurement_theta_min      ?
_cell_measurement_theta_max      ?

_exptl_crystal_description       prism
_exptl_crystal_colour            dark-green
_exptl_crystal_size_max          0.11
_exptl_crystal_size_mid          0.08
_exptl_crystal_size_min          0.06
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    2.437
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1376
_exptl_absorpt_coefficient_mu    4.459
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.6445
_exptl_absorpt_correction_T_max  0.7664
_exptl_absorpt_process_details   'SADABS (Bruker, 2002)'

_exptl_special_details           
;
?
;

_diffrn_ambient_temperature      293(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Bruker SMART CCD area detector'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            3904
_diffrn_reflns_av_R_equivalents  0.0454
_diffrn_reflns_av_sigmaI/netI    0.0619
_diffrn_reflns_limit_h_min       -5
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_theta_min         2.02
_diffrn_reflns_theta_max         25.99
_reflns_number_total             1782
_reflns_number_gt                1432
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'Bruker SMART (Bruker, 1998)'
_computing_cell_refinement       'Bruker SMART (Bruker, 1998)'
_computing_data_reduction        'Bruker SAINT + & SHELXTL (Bruker, 1998)'
_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)+(0.0515P)²+14.8749P] 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         1782
_refine_ls_number_parameters     164
_refine_ls_number_restraints     12
_refine_ls_R_factor_all          0.0755
_refine_ls_R_factor_gt           0.0581
_refine_ls_wR_factor_ref         0.1351
_refine_ls_wR_factor_gt          0.1274
_refine_ls_goodness_of_fit_ref   1.076
_refine_ls_restrained_S_all      1.073
_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 -0.60987(10) 0.45174(8) 0.71715(6) 0.0179(3) Uani 1 1 d . . .
Cu2 Cu -0.19301(13) 0.7500 0.7500 0.0154(3) Uani 1 2 d S . .
Cu3 Cu -0.15698(14) 0.7500 0.2500 0.0141(3) Uani 1 2 d S . .
O1 O -0.8008(5) 0.4021(4) 0.7623(3) 0.0146(11) Uani 1 1 d . . .
H1O H -0.7912 0.4140 0.8175 0.017 Uiso 1 1 d R . .
O2 O -0.4612(5) 0.5180(4) 0.6518(3) 0.0201(13) Uani 1 1 d . . .
O3 O -0.3662(6) 0.6282(5) 0.7400(3) 0.0261(14) Uani 1 1 d . . .
O4 O -0.3343(7) 0.6293(6) 0.3795(3) 0.0368(17) Uani 1 1 d . . .
O5 O -0.1375(6) 0.7386(4) 0.3598(3) 0.0183(12) Uani 1 1 d . . .
O6 O -0.0248(6) 0.8644(5) 0.7114(3) 0.0227(13) Uani 1 1 d . . .
O7 O 0.0858(7) 0.9195(6) 0.6040(3) 0.0438(19) Uani 1 1 d . . .
N1 N -0.1965(6) 0.7271(5) 0.6416(3) 0.0145(13) Uani 1 1 d U . .
C1 C -0.2896(7) 0.6531(6) 0.6124(4) 0.0151(16) Uani 1 1 d U . .
C2 C -0.3010(7) 0.6385(6) 0.5352(4) 0.0147(16) Uani 1 1 d U . .
H2 H -0.3661 0.5867 0.5153 0.018 Uiso 1 1 calc R . .
C3 C -0.2142(8) 0.7019(7) 0.4867(4) 0.0156(15) Uani 1 1 d U . .
C4 C -0.1162(8) 0.7774(7) 0.5170(4) 0.0178(17) Uani 1 1 d U . .
H4 H -0.0563 0.8200 0.4855 0.021 Uiso 1 1 calc R . .
C5 C -0.1100(8) 0.7876(6) 0.5964(4) 0.0170(16) Uani 1 1 d U . .
C6 C -0.3786(8) 0.5954(6) 0.6739(4) 0.0141(16) Uani 1 1 d . . .
C7 C -0.2302(9) 0.6869(7) 0.4009(4) 0.0181(17) Uani 1 1 d . . .
C8 C -0.0053(9) 0.8659(7) 0.6387(5) 0.0220(18) 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
Cu1 O2 1.931(5) . ?
Cu1 O1 1.973(5) . ?
Cu1 O4 2.024(6) 5_466 ?
Cu1 O6 2.039(5) 3_446 ?
Cu1 O1 2.122(5) 2_365 ?
Cu1 Cu1 2.766(2) 2_365 ?
Cu2 N1 1.915(6) . ?
Cu2 N1 1.915(6) 4_566 ?
Cu2 O3 2.160(6) . ?
Cu2 O3 2.160(6) 4_566 ?
Cu2 O6 2.165(5) . ?
Cu2 O6 2.165(5) 4_566 ?
Cu3 O1 1.925(5) 5_466 ?
Cu3 O1 1.925(5) 8_465 ?
Cu3 O5 1.932(5) . ?
Cu3 O5 1.932(5) 4_565 ?
O1 Cu3 1.925(5) 5_466 ?
O1 Cu1 2.122(5) 2_365 ?
O1 H1O 0.9800 . ?
O2 C6 1.266(9) . ?
O3 C6 1.229(9) . ?
O4 C7 1.227(9) . ?
O4 Cu1 2.024(6) 5_466 ?
O5 C7 1.267(9) . ?
O6 C8 1.283(9) . ?
O6 Cu1 2.039(5) 3_456 ?
O7 C8 1.210(9) . ?
N1 C5 1.332(10) . ?
N1 C1 1.336(9) . ?
C1 C2 1.365(10) . ?
C1 C6 1.513(10) . ?
C2 C3 1.388(10) . ?
C2 H2 0.9300 . ?
C3 C4 1.381(11) . ?
C3 C7 1.518(10) . ?
C4 C5 1.394(10) . ?
C4 H4 0.9300 . ?
C5 C8 1.533(10) . ?

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 Cu1 O1 163.7(2) . . ?
O2 Cu1 O4 83.3(2) . 5_466 ?
O1 Cu1 O4 88.2(2) . 5_466 ?
O2 Cu1 O6 100.5(2) . 3_446 ?
O1 Cu1 O6 95.7(2) . 3_446 ?
O4 Cu1 O6 113.2(3) 5_466 3_446 ?
O2 Cu1 O1 96.8(2) . 2_365 ?
O1 Cu1 O1 77.9(2) . 2_365 ?
O4 Cu1 O1 129.6(2) 5_466 2_365 ?
O6 Cu1 O1 116.2(2) 3_446 2_365 ?
O2 Cu1 Cu1 115.92(16) . 2_365 ?
O1 Cu1 Cu1 49.83(15) . 2_365 ?
O4 Cu1 Cu1 89.44(19) 5_466 2_365 ?
O6 Cu1 Cu1 139.34(16) 3_446 2_365 ?
O1 Cu1 Cu1 45.26(13) 2_365 2_365 ?
N1 Cu2 N1 178.2(3) . 4_566 ?
N1 Cu2 O3 78.8(2) . . ?
N1 Cu2 O3 99.8(2) 4_566 . ?
N1 Cu2 O3 99.8(2) . 4_566 ?
N1 Cu2 O3 78.8(2) 4_566 4_566 ?
O3 Cu2 O3 88.9(3) . 4_566 ?
N1 Cu2 O6 78.4(2) . . ?
N1 Cu2 O6 102.9(2) 4_566 . ?
O3 Cu2 O6 157.21(19) . . ?
O3 Cu2 O6 93.8(2) 4_566 . ?
N1 Cu2 O6 102.9(2) . 4_566 ?
N1 Cu2 O6 78.4(2) 4_566 4_566 ?
O3 Cu2 O6 93.8(2) . 4_566 ?
O3 Cu2 O6 157.21(19) 4_566 4_566 ?
O6 Cu2 O6 92.4(3) . 4_566 ?
O1 Cu3 O1 157.5(3) 5_466 8_465 ?
O1 Cu3 O5 93.3(2) 5_466 . ?
O1 Cu3 O5 88.7(2) 8_465 . ?
O1 Cu3 O5 88.7(2) 5_466 4_565 ?
O1 Cu3 O5 93.3(2) 8_465 4_565 ?
O5 Cu3 O5 169.7(3) . 4_565 ?
Cu3 O1 Cu1 115.2(2) 5_466 . ?
Cu3 O1 Cu1 135.4(3) 5_466 2_365 ?
Cu1 O1 Cu1 84.91(19) . 2_365 ?
Cu3 O1 H1O 105.8 5_466 . ?
Cu1 O1 H1O 105.8 . . ?
Cu1 O1 H1O 105.8 2_365 . ?
C6 O2 Cu1 122.5(5) . . ?
C6 O3 Cu2 111.6(5) . . ?
C7 O4 Cu1 136.6(5) . 5_466 ?
C7 O5 Cu3 122.8(5) . . ?
C8 O6 Cu1 121.3(5) . 3_456 ?
C8 O6 Cu2 114.3(5) . . ?
Cu1 O6 Cu2 124.1(3) 3_456 . ?
C5 N1 C1 121.0(6) . . ?
C5 N1 Cu2 119.7(5) . . ?
C1 N1 Cu2 119.3(5) . . ?
N1 C1 C2 121.0(7) . . ?
N1 C1 C6 112.0(6) . . ?
C2 C1 C6 127.0(7) . . ?
C1 C2 C3 119.2(7) . . ?
C1 C2 H2 120.4 . . ?
C3 C2 H2 120.4 . . ?
C4 C3 C2 119.9(7) . . ?
C4 C3 C7 121.3(7) . . ?
C2 C3 C7 118.8(7) . . ?
C3 C4 C5 117.9(7) . . ?
C3 C4 H4 121.1 . . ?
C5 C4 H4 121.1 . . ?
N1 C5 C4 121.1(7) . . ?
N1 C5 C8 114.7(7) . . ?
C4 C5 C8 124.2(7) . . ?
O3 C6 O2 126.0(7) . . ?
O3 C6 C1 117.9(7) . . ?
O2 C6 C1 116.2(7) . . ?
O4 C7 O5 127.6(7) . . ?
O4 C7 C3 116.3(7) . . ?
O5 C7 C3 116.0(7) . . ?
O7 C8 O6 126.5(7) . . ?
O7 C8 C5 120.7(7) . . ?
O6 C8 C5 112.8(7) . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
O1 H1O O7 0.98 2.29 3.028(8) 131.6 3_446

_diffrn_measured_fraction_theta_max 0.941
_diffrn_reflns_theta_full        25.99
_diffrn_measured_fraction_theta_full 0.941
_refine_diff_density_max         1.717
_refine_diff_density_min         -0.717
_refine_diff_density_rms         0.180

#========================================End

data_ligand
_database_code_depnum_ccdc_archive 'CCDC 727585'

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C8 H8 N2 O8'
_chemical_formula_weight         260.16

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 '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 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 '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                   4.8656(5)
_cell_length_b                   9.7640(12)
_cell_length_c                   11.1677(14)
_cell_angle_alpha                73.703(11)
_cell_angle_beta                 80.971(10)
_cell_angle_gamma                80.399(9)
_cell_volume                     498.69(10)
_cell_formula_units_Z            2
_cell_measurement_temperature    123(2)
_cell_measurement_reflns_used    672
_cell_measurement_theta_min      4.1467
_cell_measurement_theta_max      61.5450

_exptl_crystal_description       polyhedral
_exptl_crystal_colour            colorless
_exptl_crystal_size_max          0.32
_exptl_crystal_size_mid          0.23
_exptl_crystal_size_min          0.15
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.733
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             268
_exptl_absorpt_coefficient_mu    1.405
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.6620
_exptl_absorpt_correction_T_max  0.8169
_exptl_absorpt_process_details   
;
'Wed Jun 27 14:31:55 2007'
;

_exptl_special_details           
;
?
;

_diffrn_ambient_temperature      123(2)
_diffrn_radiation_wavelength     1.54178
_diffrn_radiation_type           CuK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Gemini S Ultra'
_diffrn_measurement_method       'ω and π scan'
_diffrn_detector_area_resol_mean 16.0855
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            2420
_diffrn_reflns_av_R_equivalents  0.0560
_diffrn_reflns_av_sigmaI/netI    0.0440
_diffrn_reflns_limit_h_min       -3
_diffrn_reflns_limit_h_max       5
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_theta_min         4.15
_diffrn_reflns_theta_max         61.43
_reflns_number_total             1401
_reflns_number_gt                972
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       
;
'Wed Jun 27 14:31:55 2007'
;
_computing_cell_refinement       
;
'Wed Jun 27 14:31:55 2007'
;
_computing_data_reduction        
;
'Wed Jun 27 14:31:55 2007'
;
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    ?
_computing_publication_material  ?

_refine_special_details          
;
Refinement of F² against ALL reflections. The weighted R-factor wR and
goodness of fit S are based on F², conventional R-factors R are based
on F, with F set to zero for negative F². The threshold expression of
F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is
not relevant to the choice of reflections for refinement. R-factors based
on F² are statistically about twice as large as those based on F, and R-
factors based on ALL data will be even larger.
;

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.1255P)²+2.1333P] 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         1401
_refine_ls_number_parameters     165
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1089
_refine_ls_R_factor_gt           0.0880
_refine_ls_wR_factor_ref         0.2658
_refine_ls_wR_factor_gt          0.2504
_refine_ls_goodness_of_fit_ref   1.075
_refine_ls_restrained_S_all      1.075
_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
O1 O 0.1820(9) 0.4678(5) 0.3746(4) 0.0412(12) Uani 1 1 d . . .
O2 O 0.0277(9) 0.4554(4) 0.2034(4) 0.0379(11) Uani 1 1 d . . .
H2O H 0.0595 0.4700 0.1236 0.05(2) Uiso 1 1 d R . .
O3 O 0.2055(8) 0.6026(4) -0.0085(4) 0.0352(11) Uani 1 1 d . . .
O4 O 0.3962(9) 0.7548(4) -0.2184(4) 0.0388(11) Uani 1 1 d . . .
H4O H 0.2902 0.6959 -0.1711 0.04(2) Uiso 1 1 d R . .
O5 O 0.6966(9) 0.9038(5) -0.2279(4) 0.0392(11) Uani 1 1 d . . .
O6 O 0.9472(9) 0.9518(4) 0.1647(4) 0.0388(11) Uani 1 1 d . . .
H6O H 1.0311 0.9962 0.2005 0.07(3) Uiso 1 1 d R . .
O7 O 0.7975(10) 0.8147(5) 0.3550(4) 0.0484(13) Uani 1 1 d . . .
N1 N 0.4848(10) 0.6856(5) 0.2389(5) 0.0312(12) Uani 1 1 d . . .
C1 C 0.3460(12) 0.6247(6) 0.1796(6) 0.0306(14) Uani 1 1 d . . .
C2 C 0.3510(11) 0.6619(6) 0.0453(6) 0.0307(14) Uani 1 1 d . . .
C3 C 0.5239(12) 0.7686(6) -0.0238(6) 0.0298(14) Uani 1 1 d . . .
C4 C 0.6687(12) 0.8299(6) 0.0398(6) 0.0301(14) Uani 1 1 d . . .
H4 H 0.7850 0.9009 -0.0056 0.036 Uiso 1 1 calc R . .
C5 C 0.6450(11) 0.7881(6) 0.1701(6) 0.0296(14) Uani 1 1 d . . .
C6 C 0.1783(12) 0.5087(6) 0.2612(6) 0.0329(14) Uani 1 1 d . . .
C7 C 0.5482(12) 0.8135(6) -0.1637(6) 0.0316(14) Uani 1 1 d . . .
C8 C 0.8001(12) 0.8498(6) 0.2413(6) 0.0332(15) Uani 1 1 d . . .
O2W O 0.340(4) 0.973(2) 0.4867(17) 0.117(5) Uiso 0.50 1 d P . .
O2W' O 0.114(4) 1.007(2) 0.489(2) 0.132(7) Uiso 0.50 1 d P . .
N2 N 0.2986(12) 0.6883(7) 0.5119(5) 0.0534(17) Uani 1 1 d . . .
H2A H 0.3639 0.6763 0.4275 0.064 Uiso 1 1 d R . .
H2B H 0.2470 0.7761 0.5124 0.064 Uiso 1 1 d R . .
H2C H 0.1467 0.6288 0.5394 0.064 Uiso 1 1 d R . .
H2D H 0.4445 0.6388 0.5607 0.064 Uiso 1 1 d 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
O1 C6 1.218(8) . ?
O2 C6 1.300(7) . ?
O2 H2O 0.8549 . ?
O3 C2 1.289(7) . ?
O4 C7 1.315(7) . ?
O4 H4O 0.8477 . ?
O5 C7 1.228(7) . ?
O6 C8 1.343(7) . ?
O6 H6O 0.8501 . ?
O7 C8 1.218(8) . ?
N1 C1 1.321(8) . ?
N1 C5 1.356(7) . ?
C1 C2 1.438(9) . ?
C1 C6 1.508(8) . ?
C2 C3 1.423(8) . ?
C3 C4 1.376(8) . ?
C3 C7 1.490(9) . ?
C4 C5 1.389(9) . ?
C4 H4 0.9500 . ?
C5 C8 1.474(8) . ?
O2W O2W' 1.09(2) . ?
O2W O2W 1.81(4) 2_676 ?
O2W' O2W' 1.12(4) 2_576 ?
N2 H2A 0.9791 . ?
N2 H2B 0.8536 . ?
N2 H2C 0.9745 . ?
N2 H2D 0.9451 . ?

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
C6 O2 H2O 119.5 . . ?
C7 O4 H4O 117.2 . . ?
C8 O6 H6O 116.0 . . ?
C1 N1 C5 118.7(5) . . ?
N1 C1 C2 123.8(5) . . ?
N1 C1 C6 116.1(5) . . ?
C2 C1 C6 120.1(5) . . ?
O3 C2 C3 122.4(6) . . ?
O3 C2 C1 121.7(5) . . ?
C3 C2 C1 115.9(5) . . ?
C4 C3 C2 119.4(6) . . ?
C4 C3 C7 120.3(5) . . ?
C2 C3 C7 120.3(5) . . ?
C3 C4 C5 120.2(6) . . ?
C3 C4 H4 119.9 . . ?
C5 C4 H4 119.9 . . ?
N1 C5 C4 122.0(5) . . ?
N1 C5 C8 116.3(5) . . ?
C4 C5 C8 121.7(5) . . ?
O1 C6 O2 121.9(6) . . ?
O1 C6 C1 122.2(5) . . ?
O2 C6 C1 116.0(5) . . ?
O5 C7 O4 119.7(6) . . ?
O5 C7 C3 123.1(5) . . ?
O4 C7 C3 117.2(5) . . ?
O7 C8 O6 123.3(6) . . ?
O7 C8 C5 125.3(6) . . ?
O6 C8 C5 111.4(5) . . ?
O2W' O2W O2W 141(2) . 2_676 ?
O2W O2W' O2W' 156(4) . 2_576 ?
H2A N2 H2B 112.8 . . ?
H2A N2 H2C 102.4 . . ?
H2B N2 H2C 113.5 . . ?
H2A N2 H2D 105.0 . . ?
H2B N2 H2D 116.4 . . ?
H2C N2 H2D 105.5 . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
O2 H2O O3 0.85 1.81 2.505(6) 137.7 .
O2 H2O O3 0.85 2.27 2.833(6) 123.5 2_565
O4 H4O O3 0.85 1.81 2.527(6) 141.9 .
O4 H4O O2 0.85 2.44 3.099(6) 135.4 2_565
O6 H6O O5 0.85 1.88 2.692(6) 159.8 2_775
N2 H2A N1 0.98 2.08 3.048(8) 171.0 .
N2 H2B O2W 0.85 1.98 2.751(19) 149.8 .
N2 H2B O2W' 0.85 2.19 3.04(2) 173.1 .
N2 H2C O1 0.97 1.97 2.928(7) 166.8 2_566
N2 H2D O1 0.95 2.07 2.992(7) 166.1 2_666

_diffrn_measured_fraction_theta_max 0.903
_diffrn_reflns_theta_full        61.43
_diffrn_measured_fraction_theta_full 0.903
_refine_diff_density_max         0.393
_refine_diff_density_min         -0.428
_refine_diff_density_rms         0.102

#_eof
#End of Crystallographic Information File


