Electronic Supplementary Material for CrystEngComm
This Journal is (c) The Royal Society of Chemistry 2006

data_global
_journal_name_full               CrystEngComm

_journal_coden_Cambridge         1350

_publ_contact_author_name        'Catalina Ruiz-Perez'
_publ_contact_author_address     
;
Departamento de Fisica Fundamental II
Universidad de La Laguna
Avda Astrofisico Francisco Sanchez
La Laguna
Tenerife
38204
SPAIN
;

_publ_contact_author_email       CARUIZ@ULL.ES

_publ_section_title              
;
Versatile supramolecular self-assembly. Part II.
Network formation and magnetic behaviour of copper(II) malonate anions
in ammonium derivatives.
;
loop_
_publ_author_name
'Catalina Ruiz-Perez'
'Fernando S. Delgado'
'Miguel Julve'
'F. Lloret'
'Joaquin Shanchiz'

# Attachment 'compound1a.cif'

data_compound1a
_database_code_depnum_ccdc_archive 'CCDC 253062'

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C6 H12 Cu N2 O8'
_chemical_formula_weight         303.72

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'
Cu Cu 0.3201 1.2651 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_H-M   'F d d 2'
_symmetry_space_group_name_Hall  'F 2 -2 d'
_symmetry_Int_Tables_number      43

loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, z'
'-x+1/4, y+1/4, z+1/4'
'x+3/4, -y+3/4, z+1/4'
'x, y+1/2, z+1/2'
'-x, -y+1/2, z+1/2'
'-x+1/4, y+3/4, z+3/4'
'x+3/4, -y+5/4, z+3/4'
'x+1/2, y, z+1/2'
'-x+1/2, -y, z+1/2'
'-x+3/4, y+1/4, z+3/4'
'x+5/4, -y+3/4, z+3/4'
'x+1/2, y+1/2, z'
'-x+1/2, -y+1/2, z'
'-x+3/4, y+3/4, z+1/4'
'x+5/4, -y+5/4, z+1/4'

_cell_length_a                   13.8481(3)
_cell_length_b                   16.4536(2)
_cell_length_c                   9.1071(2)
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_volume                     2075.06(7)
_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       'irregular prism'
_exptl_crystal_colour            'palid blue'
_exptl_crystal_size_max          0.36
_exptl_crystal_size_mid          0.27
_exptl_crystal_size_min          0.18
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.944
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1240
_exptl_absorpt_coefficient_mu    2.142
_exptl_absorpt_correction_type   Multi-scan
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   '(SADABS, Sheldrick, Bruker, 2000)'

_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  'horizonally mounted graphite crystal'
_diffrn_radiation_probe          x-ray
_diffrn_source                   'Enraf Nonius FR590'
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 9
_diffrn_measurement_device       '95mm CCD camera on \k-goniostat'
_diffrn_measurement_device_type  KappaCCD
_diffrn_measurement_method       'CCD rotation images, thick slices'
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            3607
_diffrn_reflns_av_R_equivalents  0.0225
_diffrn_reflns_av_sigmaI/netI    0.0256
_diffrn_reflns_limit_h_min       -19
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_k_min       -23
_diffrn_reflns_limit_k_max       22
_diffrn_reflns_limit_l_min       -10
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_theta_min         6.76
_diffrn_reflns_theta_max         29.98
_reflns_number_total             1264
_reflns_number_gt                1171
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'Collect (Nonius BV, 1997-2000)'
_computing_cell_refinement       'Dirax/lsq (Duisenberg & Schreurs, 1989-2000)'
_computing_data_reduction        'EvalCCD (Duisenberg & Schreurs 1990-2000)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1997)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    'Ortep-3 for Windows (Farrugia, 1997)'
_computing_publication_material  'WinGX publication routines (Farrugia, 1999)'

_refine_special_details          
;
Refinement of F^2^ against ALL reflections. The weighted R-factor wR and
goodness of fit S are based on F^2^, conventional R-factors R are based
on F, with F set to zero for negative F^2^. The threshold expression of
F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is
not relevant to the choice of reflections for refinement. R-factors based
on F^2^ 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/[\s^2^(Fo^2^)+(0.0272P)^2^+0.7267P] where P=(Fo^2^+2Fc^2^)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0.542(16)
_refine_ls_number_reflns         1264
_refine_ls_number_parameters     103
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0244
_refine_ls_R_factor_gt           0.0197
_refine_ls_wR_factor_ref         0.0491
_refine_ls_wR_factor_gt          0.0479
_refine_ls_goodness_of_fit_ref   1.073
_refine_ls_restrained_S_all      1.072
_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 0.2500 -0.2500 0.43900(5) 0.01724(9) Uani 1 2 d S . .
O1 O 0.21229(13) -0.17406(9) 0.28414(17) 0.0227(3) Uani 1 1 d . . .
O2 O 0.21208(14) -0.17562(9) 0.59373(16) 0.0237(3) Uani 1 1 d . . .
O3 O 0.13782(11) -0.06466(8) 0.20482(19) 0.0236(3) Uani 1 1 d . . .
O4 O 0.16466(10) -0.05947(7) 0.6896(2) 0.0246(3) Uani 1 1 d . . .
C1 C 0.18471(14) -0.10152(12) 0.3016(2) 0.0159(4) Uani 1 1 d . . .
C2 C 0.21193(14) -0.05594(10) 0.4395(3) 0.0188(3) Uani 1 1 d . . .
C3 C 0.19461(14) -0.09998(13) 0.5827(2) 0.0158(4) Uani 1 1 d . . .
N11 N 0.18009(13) -0.15173(10) -0.0560(3) 0.0231(3) Uani 1 1 d . . .
H11 H 0.163(2) -0.127(2) 0.018(4) 0.027(8) Uiso 1 1 d . . .
H12 H 0.1480(16) -0.1994(14) -0.066(4) 0.025(5) Uiso 1 1 d . . .
H13 H 0.167(4) -0.125(3) -0.129(6) 0.064(13) Uiso 1 1 d . . .
H14 H 0.2424(18) -0.1609(13) -0.032(3) 0.020(6) Uiso 1 1 d . . .
H1 H 0.1911(17) -0.0054(12) 0.444(3) 0.024(6) Uiso 1 1 d . . .
H2 H 0.2774(18) -0.0472(12) 0.428(5) 0.023(6) Uiso 1 1 d . . .

loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_23
_atom_site_aniso_U_13
_atom_site_aniso_U_12
Cu1 0.02803(15) 0.01257(12) 0.01112(13) 0.000 0.000 0.00352(12)
O1 0.0362(10) 0.0155(7) 0.0163(8) -0.0004(6) -0.0044(7) 0.0050(6)
O2 0.0401(10) 0.0174(7) 0.0138(7) 0.0009(6) 0.0039(7) 0.0050(7)
O3 0.0301(7) 0.0239(6) 0.0169(9) 0.0015(8) -0.0042(7) 0.0087(5)
O4 0.0373(7) 0.0220(6) 0.0143(6) -0.0029(8) 0.0023(8) 0.0080(5)
C1 0.0180(9) 0.0164(8) 0.0133(10) 0.0010(8) 0.0016(7) -0.0011(7)
C2 0.0271(8) 0.0141(7) 0.0150(8) -0.0022(9) 0.0016(10) 0.0003(6)
C3 0.0155(9) 0.0194(9) 0.0126(9) -0.0009(7) -0.0005(7) 0.0003(7)
N11 0.0283(8) 0.0229(7) 0.0180(8) 0.0020(10) 0.0007(10) -0.0011(6)

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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Cu1 O2 1.9389(15) . ?
Cu1 O2 1.9389(15) 14_545 ?
Cu1 O1 1.9553(16) 14_545 ?
Cu1 O1 1.9553(16) . ?
O1 C1 1.263(2) . ?
O2 C3 1.272(2) . ?
O3 C1 1.251(3) . ?
O4 C3 1.250(3) . ?
C1 C2 1.511(3) . ?
C2 C3 1.511(3) . ?

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 O2 86.77(9) . 14_545 ?
O2 Cu1 O1 179.41(8) . 14_545 ?
O2 Cu1 O1 92.78(5) 14_545 14_545 ?
O2 Cu1 O1 92.78(5) . . ?
O2 Cu1 O1 179.41(8) 14_545 . ?
O1 Cu1 O1 87.68(9) 14_545 . ?
C1 O1 Cu1 126.44(14) . . ?
C3 O2 Cu1 127.72(14) . . ?
O3 C1 O1 121.77(19) . . ?
O3 C1 C2 118.32(18) . . ?
O1 C1 C2 119.86(18) . . ?
C3 C2 C1 116.11(14) . . ?
O4 C3 O2 121.6(2) . . ?
O4 C3 C2 117.95(19) . . ?
O2 C3 C2 120.48(18) . . ?

_diffrn_measured_fraction_theta_max 0.985
_diffrn_reflns_theta_full        29.98
_diffrn_measured_fraction_theta_full 0.985
_refine_diff_density_max         0.247
_refine_diff_density_min         -0.253
_refine_diff_density_rms         0.051

# Attachment 'compound2.cif'

data_compound2
_database_code_depnum_ccdc_archive 'CCDC 253063'

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C8 H16 Cu N2 O8'
_chemical_formula_weight         331.77

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'
Cu Cu 0.3201 1.2651 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_H-M   'P 21/c'
_symmetry_space_group_name_Hall  '-P 2ybc'
_symmetry_Int_Tables_number      14

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                   8.6866(2)
_cell_length_b                   9.0585(3)
_cell_length_c                   8.9681(3)
_cell_angle_alpha                90.00
_cell_angle_beta                 115.198(2)
_cell_angle_gamma                90.00
_cell_volume                     638.53(3)
_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
_exptl_crystal_colour            blue
_exptl_crystal_size_max          0.20
_exptl_crystal_size_mid          0.16
_exptl_crystal_size_min          0.06
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.726
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             342
_exptl_absorpt_coefficient_mu    1.748
_exptl_absorpt_correction_type   Multi-scan
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   '(SADABS, Sheldrick, Bruker, 2000)'

_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  'horizonally mounted graphite crystal'
_diffrn_radiation_probe          x-ray
_diffrn_source                   'Enraf Nonius FR590'
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 9
_diffrn_measurement_device       '95mm CCD camera on \k-goniostat'
_diffrn_measurement_device_type  KappaCCD
_diffrn_measurement_method       'CCD rotation images, thick slices'
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            3684
_diffrn_reflns_av_R_equivalents  0.0154
_diffrn_reflns_av_sigmaI/netI    0.0193
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_theta_min         6.42
_diffrn_reflns_theta_max         27.50
_reflns_number_total             1449
_reflns_number_gt                1255
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'Collect (Nonius BV, 1997-2000)'
_computing_cell_refinement       'Dirax/lsq (Duisenberg & Schreurs, 1989-2000)'
_computing_data_reduction        'EvalCCD (Duisenberg & Schreurs 1990-2000)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1997)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    'Ortep-3 for Windows (Farrugia, 1997)'
_computing_publication_material  'WinGX publication routines (Farrugia, 1999)'

_refine_special_details          
;
Refinement of F^2^ against ALL reflections. The weighted R-factor wR and
goodness of fit S are based on F^2^, conventional R-factors R are based
on F, with F set to zero for negative F^2^. The threshold expression of
F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is
not relevant to the choice of reflections for refinement. R-factors based
on F^2^ 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/[\s^2^(Fo^2^)+(0.0351P)^2^+0.1243P] where P=(Fo^2^+2Fc^2^)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   difmap
_refine_ls_hydrogen_treatment    refall
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         1449
_refine_ls_number_parameters     120
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0298
_refine_ls_R_factor_gt           0.0228
_refine_ls_wR_factor_ref         0.0620
_refine_ls_wR_factor_gt          0.0594
_refine_ls_goodness_of_fit_ref   1.104
_refine_ls_restrained_S_all      1.104
_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 0.5000 0.0000 0.02424(11) Uani 1 2 d S . .
O1 O -0.07152(14) 0.31937(13) -0.12325(15) 0.0311(3) Uani 1 1 d . . .
O2 O 0.24065(13) 0.44597(14) 0.08020(12) 0.0249(2) Uani 1 1 d . . .
O3 O -0.04455(17) 0.13676(15) -0.27147(17) 0.0411(3) Uani 1 1 d . . .
O4 O 0.44600(15) 0.31529(16) 0.06217(14) 0.0381(3) Uani 1 1 d . . .
C1 C 0.01102(19) 0.24961(17) -0.18955(19) 0.0230(3) Uani 1 1 d . . .
C2 C 0.1795(2) 0.31266(19) -0.17045(18) 0.0239(3) Uani 1 1 d . . .
C3 C 0.29643(18) 0.36156(16) 0.00228(17) 0.0218(3) Uani 1 1 d . . .
N11 N 0.6364(2) 0.29344(19) 0.3983(2) 0.0322(3) Uani 1 1 d . . .
C11 C 0.6973(4) 0.4391(3) 0.4691(3) 0.0502(5) Uani 1 1 d . . .
H1 H 0.233(3) 0.242(2) -0.210(2) 0.031(5) Uiso 1 1 d . . .
H2 H 0.156(3) 0.398(2) -0.232(2) 0.033(5) Uiso 1 1 d . . .
H11 H 0.568(3) 0.300(3) 0.289(3) 0.046(6) Uiso 1 1 d . . .
H12 H 0.583(3) 0.245(3) 0.447(3) 0.048(6) Uiso 1 1 d . . .
H13 H 0.715(3) 0.243(3) 0.411(3) 0.043(6) Uiso 1 1 d . . .
H14 H 0.624(5) 0.499(3) 0.423(5) 0.077(11) Uiso 1 1 d . . .
H15 H 0.739(4) 0.443(3) 0.592(4) 0.064(7) Uiso 1 1 d . . .
H16 H 0.793(6) 0.469(4) 0.444(4) 0.090(11) Uiso 1 1 d . . .

loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_23
_atom_site_aniso_U_13
_atom_site_aniso_U_12
Cu1 0.01684(14) 0.02190(16) 0.03468(17) -0.01057(10) 0.01165(11) -0.00196(10)
O1 0.0248(6) 0.0275(6) 0.0466(6) -0.0158(5) 0.0206(5) -0.0077(5)
O2 0.0190(5) 0.0296(6) 0.0263(5) -0.0064(4) 0.0098(4) 0.0006(5)
O3 0.0438(7) 0.0323(7) 0.0537(7) -0.0232(6) 0.0270(6) -0.0130(6)
O4 0.0228(6) 0.0547(8) 0.0336(6) -0.0052(6) 0.0089(5) 0.0127(6)
C1 0.0242(7) 0.0202(8) 0.0234(6) -0.0017(5) 0.0091(5) 0.0007(6)
C2 0.0250(7) 0.0260(8) 0.0234(7) -0.0028(6) 0.0129(6) 0.0012(6)
C3 0.0196(7) 0.0223(7) 0.0248(7) 0.0017(5) 0.0108(6) 0.0005(6)
N11 0.0238(7) 0.0392(9) 0.0347(8) 0.0014(6) 0.0134(6) 0.0045(7)
C11 0.0578(14) 0.0411(12) 0.0543(13) -0.0006(10) 0.0265(11) -0.0041(12)

_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 1.9236(11) . ?
Cu1 O1 1.9236(11) 3_565 ?
Cu1 O2 1.9613(10) . ?
Cu1 O2 1.9613(10) 3_565 ?
Cu1 O3 2.5620(15) 4_566 ?
Cu1 O3 2.5620(15) 2_554 ?
O1 C1 1.2767(19) . ?
O2 C3 1.2633(18) . ?
O3 C1 1.2312(19) . ?
O4 C3 1.2483(18) . ?
C1 C2 1.511(2) . ?
C2 C3 1.513(2) . ?
N11 C11 1.463(3) . ?

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 180.0 . 3_565 ?
O1 Cu1 O2 91.81(5) . . ?
O1 Cu1 O2 88.19(5) 3_565 . ?
O1 Cu1 O2 88.19(5) . 3_565 ?
O1 Cu1 O2 91.81(5) 3_565 3_565 ?
O2 Cu1 O2 180.0 . 3_565 ?
O3 Cu1 O1 85.77(4) 4_566 . ?
O3 Cu1 O2 94.96(5) 4_566 . ?
O3 Cu1 O1 94.23(4) 4_566 3_565 ?
O3 Cu1 O2 85.04(5) 4_566 3_565 ?
O3 Cu1 O1 94.23(4) 2_554 . ?
O3 Cu1 O2 85.04(5) 2_554 . ?
O3 Cu1 O1 85.77(4) 2_554 3_565 ?
O3 Cu1 O2 94.96(5) 2_554 3_565 ?
O3 Cu1 O3 180.0 4_566 2_554 ?
C1 O1 Cu1 125.49(10) . . ?
C3 O2 Cu1 123.24(9) . . ?
O3 C1 O1 122.25(15) . . ?
O3 C1 C2 119.74(14) . . ?
O1 C1 C2 117.96(13) . . ?
C1 C2 C3 114.99(12) . . ?
O4 C3 O2 122.64(13) . . ?
O4 C3 C2 117.67(14) . . ?
O2 C3 C2 119.69(13) . . ?

_diffrn_measured_fraction_theta_max 0.986
_diffrn_reflns_theta_full        27.50
_diffrn_measured_fraction_theta_full 0.986
_refine_diff_density_max         0.244
_refine_diff_density_min         -0.438
_refine_diff_density_rms         0.063

# Attachment 'compound3.cif'

data_compound3
_database_code_depnum_ccdc_archive 'CCDC 253064'

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C8 H20 Cu N2 O11'
_chemical_formula_weight         383.80

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   'P 21/c'
_symmetry_space_group_name_Hall  '-P 2ybc'
_symmetry_Int_Tables_number      14

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                   11.670(2)
_cell_length_b                   8.408(2)
_cell_length_c                   15.323(3)
_cell_angle_alpha                90.00
_cell_angle_beta                 93.38(3)
_cell_angle_gamma                90.00
_cell_volume                     1500.9(5)
_cell_formula_units_Z            4
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    ?
_cell_measurement_theta_min      ?
_cell_measurement_theta_max      ?

_exptl_crystal_description       prism
_exptl_crystal_colour            blue
_exptl_crystal_size_max          1
_exptl_crystal_size_mid          0.8
_exptl_crystal_size_min          0.6
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.698
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             796
_exptl_absorpt_coefficient_mu    1.514
_exptl_absorpt_correction_type   Multi-scan
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   '(SADABS, Sheldrick, Bruker, 2000)'

_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  'horizonally mounted graphite crystal'
_diffrn_radiation_probe          x-ray
_diffrn_source                   'Enraf Nonius FR590'
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 9
_diffrn_measurement_device       '95mm CCD camera on \k-goniostat'
_diffrn_measurement_device_type  KappaCCD
_diffrn_measurement_method       'CCD rotation images, thick slices'
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            10895
_diffrn_reflns_av_R_equivalents  0.0348
_diffrn_reflns_av_sigmaI/netI    0.0339
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_theta_min         6.47
_diffrn_reflns_theta_max         27.50
_reflns_number_total             3321
_reflns_number_gt                2815
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'Collect (Nonius BV, 1997-2000)'
_computing_cell_refinement       'Dirax/lsq (Duisenberg & Schreurs, 1989-2000)'
_computing_data_reduction        'EvalCCD (Duisenberg & Schreurs 1990-2000)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1997)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    'Ortep-3 for Windows (Farrugia, 1997)'
_computing_publication_material  'WinGX publication routines (Farrugia, 1999)'

_refine_special_details          
;
Refinement of F^2^ against ALL reflections. The weighted R-factor wR and
goodness of fit S are based on F^2^, conventional R-factors R are based
on F, with F set to zero for negative F^2^. The threshold expression of
F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is
not relevant to the choice of reflections for refinement. R-factors based
on F^2^ 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/[\s^2^(Fo^2^)+(0.0577P)^2^+1.1076P] where P=(Fo^2^+2Fc^2^)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   difmap
_refine_ls_hydrogen_treatment    refall
_refine_ls_extinction_method     SHELXL
_refine_ls_extinction_coef       0.114(4)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^
_refine_ls_number_reflns         3321
_refine_ls_number_parameters     256
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0484
_refine_ls_R_factor_gt           0.0392
_refine_ls_wR_factor_ref         0.1081
_refine_ls_wR_factor_gt          0.1018
_refine_ls_goodness_of_fit_ref   1.094
_refine_ls_restrained_S_all      1.094
_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 0.25451(2) 0.19386(3) 0.753927(17) 0.02224(15) Uani 1 1 d . . .
O1 O 0.20186(14) 0.39955(19) 0.78941(11) 0.0272(4) Uani 1 1 d . . .
O2 O 0.14322(14) 0.08290(19) 0.82063(11) 0.0270(4) Uani 1 1 d . . .
O3 O 0.08034(16) 0.5695(2) 0.83999(13) 0.0350(4) Uani 1 1 d . . .
O4 O -0.02074(16) 0.0516(2) 0.88180(13) 0.0339(4) Uani 1 1 d . . .
C1 C 0.1065(2) 0.4327(3) 0.81928(14) 0.0219(5) Uani 1 1 d . . .
C2 C 0.0147(2) 0.3066(3) 0.8259(2) 0.0372(7) Uani 1 1 d . . .
C3 C 0.0482(2) 0.1362(3) 0.84505(14) 0.0225(5) Uani 1 1 d . . .
O11 O 0.36491(14) 0.30616(18) 0.68738(11) 0.0238(4) Uani 1 1 d . . .
O12 O 0.29671(14) -0.01019(19) 0.70904(11) 0.0280(4) Uani 1 1 d . . .
O13 O 0.52607(15) 0.3363(2) 0.62181(13) 0.0298(4) Uani 1 1 d . . .
O14 O 0.41059(16) -0.1820(2) 0.65208(14) 0.0341(4) Uani 1 1 d . . .
C11 C 0.45633(19) 0.2506(3) 0.65753(14) 0.0205(4) Uani 1 1 d . . .
C12 C 0.4848(2) 0.0762(3) 0.6683(2) 0.0295(5) Uani 1 1 d . . .
C13 C 0.3899(2) -0.0449(3) 0.67623(14) 0.0224(5) Uani 1 1 d . . .
N21 N 0.25934(19) 0.5794(3) 0.62073(13) 0.0237(4) Uani 1 1 d . . .
N22 N 0.23806(19) 0.7047(3) 0.38584(13) 0.0244(4) Uani 1 1 d . . .
C21 C 0.2746(2) 0.5672(3) 0.52600(15) 0.0269(5) Uani 1 1 d . . .
C22 C 0.2193(3) 0.7085(3) 0.48036(16) 0.0276(5) Uani 1 1 d . . .
O1W O 0.39391(16) 0.1617(2) 0.87792(12) 0.0333(4) Uani 1 1 d . . .
O2W O 0.1074(2) 0.2328(3) 0.60791(19) 0.0571(6) Uani 1 1 d . . .
O3W O 0.2873(3) 0.1047(3) 0.50084(17) 0.0706(8) Uani 1 1 d . . .
H1 H -0.042(3) 0.343(5) 0.868(2) 0.051(10) Uiso 1 1 d . . .
H2 H -0.037(4) 0.301(5) 0.765(3) 0.077(13) Uiso 1 1 d . . .
H11 H 0.532(3) 0.048(4) 0.623(2) 0.038(8) Uiso 1 1 d . . .
H12 H 0.535(3) 0.067(5) 0.722(3) 0.064(11) Uiso 1 1 d . . .
H21 H 0.294(3) 0.665(4) 0.642(2) 0.028(7) Uiso 1 1 d . . .
H22 H 0.184(3) 0.582(3) 0.6287(19) 0.028(7) Uiso 1 1 d . . .
H23 H 0.294(3) 0.494(4) 0.6507(19) 0.029(7) Uiso 1 1 d . . .
H24 H 0.245(3) 0.464(3) 0.5063(18) 0.026(7) Uiso 1 1 d . . .
H25 H 0.352(3) 0.567(4) 0.523(2) 0.036(8) Uiso 1 1 d . . .
H26 H 0.253(3) 0.808(4) 0.502(2) 0.051(10) Uiso 1 1 d . . .
H27 H 0.147(3) 0.701(3) 0.484(2) 0.034(8) Uiso 1 1 d . . .
H28 H 0.203(3) 0.610(4) 0.358(2) 0.043(9) Uiso 1 1 d . . .
H29 H 0.316(3) 0.706(4) 0.378(2) 0.042(9) Uiso 1 1 d . . .
H30 H 0.203(3) 0.791(4) 0.359(2) 0.033(8) Uiso 1 1 d . . .

loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_23
_atom_site_aniso_U_13
_atom_site_aniso_U_12
Cu1 0.0227(2) 0.0157(2) 0.0296(2) 0.00154(10) 0.01245(12) 0.00024(10)
O1 0.0264(9) 0.0201(8) 0.0363(9) -0.0019(7) 0.0124(7) -0.0013(7)
O2 0.0221(8) 0.0206(8) 0.0398(9) 0.0067(7) 0.0139(7) 0.0032(6)
O3 0.0299(10) 0.0212(9) 0.0539(11) -0.0123(8) 0.0043(8) 0.0017(7)
O4 0.0272(10) 0.0306(10) 0.0457(10) 0.0071(8) 0.0165(8) -0.0021(7)
C1 0.0220(11) 0.0203(11) 0.0232(10) -0.0014(8) 0.0010(8) 0.0017(8)
C2 0.0213(13) 0.0214(14) 0.070(2) 0.0034(12) 0.0145(13) 0.0023(9)
C3 0.0206(11) 0.0214(12) 0.0258(11) -0.0005(9) 0.0045(8) -0.0006(9)
O11 0.0219(8) 0.0188(8) 0.0320(8) 0.0045(6) 0.0111(7) 0.0018(6)
O12 0.0256(9) 0.0185(8) 0.0412(9) -0.0031(7) 0.0119(7) -0.0005(7)
O13 0.0244(9) 0.0256(9) 0.0411(10) 0.0042(7) 0.0147(7) -0.0025(7)
O14 0.0282(10) 0.0197(9) 0.0549(11) -0.0109(7) 0.0063(8) 0.0011(7)
C11 0.0205(11) 0.0204(11) 0.0208(10) -0.0006(8) 0.0015(8) -0.0003(8)
C12 0.0195(12) 0.0223(12) 0.0474(15) -0.0006(11) 0.0089(11) 0.0014(9)
C13 0.0216(12) 0.0209(11) 0.0246(10) -0.0002(8) 0.0004(8) 0.0011(8)
N21 0.0234(11) 0.0234(11) 0.0246(9) 0.0032(8) 0.0034(8) -0.0004(9)
N22 0.0257(11) 0.0232(11) 0.0244(10) 0.0029(8) 0.0029(8) 0.0018(8)
C21 0.0314(14) 0.0246(13) 0.0250(11) 0.0001(9) 0.0049(9) 0.0057(10)
C22 0.0311(15) 0.0265(13) 0.0256(12) 0.0005(9) 0.0046(10) 0.0066(10)
O1W 0.0253(10) 0.0363(10) 0.0387(10) 0.0049(8) 0.0067(8) -0.0028(8)
O2W 0.0365(13) 0.0430(13) 0.0941(19) -0.0022(12) 0.0231(12) -0.0045(10)
O3W 0.103(2) 0.0526(15) 0.0589(15) 0.0037(12) 0.0250(15) 0.0032(14)

_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 O12 1.9233(17) . ?
Cu1 O1 1.9245(17) . ?
Cu1 O11 1.9355(16) . ?
Cu1 O2 1.9386(17) . ?
Cu1 O1W 2.442(2) . ?
Cu1 O2W 2.758(3) . ?
O1 C1 1.259(3) . ?
O2 C3 1.272(3) . ?
O3 C1 1.236(3) . ?
O4 C3 1.234(3) . ?
C1 C2 1.514(3) . ?
C2 C3 1.510(3) . ?
C2 H1 1.00(4) . ?
C2 H2 1.09(5) . ?
O11 C11 1.274(3) . ?
O12 C13 1.259(3) . ?
O13 C11 1.239(3) . ?
O14 C13 1.239(3) . ?
C11 C12 1.510(3) . ?
C12 C13 1.514(3) . ?
C12 H11 0.94(4) . ?
C12 H12 0.99(4) . ?
N21 C21 1.477(3) . ?
N21 H21 0.88(3) . ?
N21 H22 0.89(3) . ?
N21 H23 0.94(3) . ?
N22 C22 1.478(3) . ?
N22 H28 0.98(4) . ?
N22 H29 0.93(4) . ?
N22 H30 0.92(3) . ?
C21 C22 1.505(3) . ?
C21 H24 0.98(3) . ?
C21 H25 0.90(3) . ?
C22 H26 0.98(4) . ?
C22 H27 0.85(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
O12 Cu1 O1 174.52(7) . . ?
O12 Cu1 O11 93.11(7) . . ?
O1 Cu1 O11 86.79(7) . . ?
O12 Cu1 O2 87.30(7) . . ?
O1 Cu1 O2 92.78(7) . . ?
O11 Cu1 O2 179.55(6) . . ?
O1W Cu1 O1 95.10(7) . . ?
O1W Cu1 O2 88.44(7) . . ?
O1W Cu1 O11 91.74(7) . . ?
O1W Cu1 O12 90.37(7) . . ?
O2W Cu1 O1 85.91(7) . . ?
O2W Cu1 O2 94.63(7) . . ?
O2W Cu1 O11 85.20(7) . . ?
O2W Cu1 O12 88.62(7) . . ?
O1W Cu1 O2W 176.72(7) . . ?
C1 O1 Cu1 127.25(15) . . ?
C3 O2 Cu1 127.46(15) . . ?
O3 C1 O1 122.4(2) . . ?
O3 C1 C2 116.6(2) . . ?
O1 C1 C2 120.9(2) . . ?
C3 C2 C1 120.1(2) . . ?
C3 C2 H1 110(2) . . ?
C1 C2 H1 109(2) . . ?
C3 C2 H2 104(2) . . ?
C1 C2 H2 109(2) . . ?
H1 C2 H2 103(3) . . ?
O4 C3 O2 122.3(2) . . ?
O4 C3 C2 117.8(2) . . ?
O2 C3 C2 119.8(2) . . ?
C11 O11 Cu1 127.42(15) . . ?
C13 O12 Cu1 126.49(15) . . ?
O13 C11 O11 122.1(2) . . ?
O13 C11 C12 117.9(2) . . ?
O11 C11 C12 120.0(2) . . ?
C11 C12 C13 120.3(2) . . ?
C11 C12 H11 107(2) . . ?
C13 C12 H11 111(2) . . ?
C11 C12 H12 107(2) . . ?
C13 C12 H12 106(2) . . ?
H11 C12 H12 105(3) . . ?
O14 C13 O12 121.5(2) . . ?
O14 C13 C12 116.5(2) . . ?
O12 C13 C12 122.0(2) . . ?
C21 N21 H21 110(2) . . ?
C21 N21 H22 108.2(19) . . ?
H21 N21 H22 111(3) . . ?
C21 N21 H23 110.8(18) . . ?
H21 N21 H23 106(3) . . ?
H22 N21 H23 111(3) . . ?
C22 N22 H28 111(2) . . ?
C22 N22 H29 109(2) . . ?
H28 N22 H29 110(3) . . ?
C22 N22 H30 109(2) . . ?
H28 N22 H30 107(3) . . ?
H29 N22 H30 110(3) . . ?
N21 C21 C22 109.2(2) . . ?
N21 C21 H24 107.6(16) . . ?
C22 C21 H24 114.9(16) . . ?
N21 C21 H25 103(2) . . ?
C22 C21 H25 112(2) . . ?
H24 C21 H25 109(3) . . ?
N22 C22 C21 110.7(2) . . ?
N22 C22 H26 106(2) . . ?
C21 C22 H26 111(2) . . ?
N22 C22 H27 106(2) . . ?
C21 C22 H27 108(2) . . ?
H26 C22 H27 115(3) . . ?

_diffrn_measured_fraction_theta_max 0.964
_diffrn_reflns_theta_full        27.50
_diffrn_measured_fraction_theta_full 0.964
_refine_diff_density_max         0.659
_refine_diff_density_min         -0.978
_refine_diff_density_rms         0.120

# Attachment 'compound4.cif'

data_compound4
_database_code_depnum_ccdc_archive 'CCDC 253065'

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C9 H16 Cu N2 O8'
_chemical_formula_weight         343.78

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'
Cu Cu 0.3201 1.2651 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_H-M   'P b c n'
_symmetry_space_group_name_Hall  '-P 2n 2ab'
_symmetry_Int_Tables_number      60

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

_cell_length_a                   8.2680(4)
_cell_length_b                   16.9351(9)
_cell_length_c                   9.4736(5)
_cell_angle_alpha                90.000(5)
_cell_angle_beta                 90.000(4)
_cell_angle_gamma                90.000(4)
_cell_volume                     1326.49(12)
_cell_formula_units_Z            4
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    ?
_cell_measurement_theta_min      ?
_cell_measurement_theta_max      ?

_exptl_crystal_description       'rectangular sheet'
_exptl_crystal_colour            'dark blue'
_exptl_crystal_size_max          0.6
_exptl_crystal_size_mid          0.39
_exptl_crystal_size_min          0.16
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.721
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             708
_exptl_absorpt_coefficient_mu    1.686
_exptl_absorpt_correction_type   Multi-scan
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   '(SADABS, Sheldrick, Bruker, 2000)'

_exptl_special_details           
;
?
;

_diffrn_ambient_temperature      293(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           Mok\a
_diffrn_radiation_monochromator  'horizonally mounted graphite crystal'
_diffrn_radiation_probe          x-ray
_diffrn_source                   'Enraf Nonius FR590'
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 9
_diffrn_measurement_device       '95mm CCD camera on \k-goniostat'
_diffrn_measurement_device_type  KappaCCD
_diffrn_measurement_method       'CCD rotation images, thick slices'
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            5634
_diffrn_reflns_av_R_equivalents  0.0218
_diffrn_reflns_av_sigmaI/netI    0.0236
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_k_max       22
_diffrn_reflns_limit_l_min       -9
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_theta_min         5.10
_diffrn_reflns_theta_max         27.50
_reflns_number_total             1425
_reflns_number_gt                1144
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'Collect (Nonius BV, 1997-2000)'
_computing_cell_refinement       'Dirax/lsq (Duisenberg & Schreurs, 1989-2000)'
_computing_data_reduction        'EvalCCD (Duisenberg & Schreurs 1990-2000)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1997)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    'Ortep-3 for Windows (Farrugia, 1997)'
_computing_publication_material  'WinGX publication routines (Farrugia, 1999)'

_refine_special_details          
;
Refinement of F^2^ against ALL reflections. The weighted R-factor wR and
goodness of fit S are based on F^2^, conventional R-factors R are based
on F, with F set to zero for negative F^2^. The threshold expression of
F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is
not relevant to the choice of reflections for refinement. R-factors based
on F^2^ 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/[\s^2^(Fo^2^)+(0.0288P)^2^+2.5515P] where P=(Fo^2^+2Fc^2^)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   difmap
_refine_ls_hydrogen_treatment    refall
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         1425
_refine_ls_number_parameters     124
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0581
_refine_ls_R_factor_gt           0.0426
_refine_ls_wR_factor_ref         0.0960
_refine_ls_wR_factor_gt          0.0905
_refine_ls_goodness_of_fit_ref   1.106
_refine_ls_restrained_S_all      1.106
_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 0.20442(3) 0.2500 0.0459(2) Uani 1 2 d S . .
O1 O 0.1055(4) 0.28570(13) 0.3570(3) 0.0623(9) Uani 1 1 d . . .
O2 O 0.0753(3) 0.12403(11) 0.3753(2) 0.0319(5) Uani 1 1 d . . .
O3 O 0.2116(4) 0.33796(15) 0.5461(2) 0.0534(7) Uani 1 1 d . . .
O4 O 0.1244(3) 0.07427(13) 0.5834(2) 0.0399(6) Uani 1 1 d . . .
C1 C 0.1399(4) 0.28357(18) 0.4867(3) 0.0349(7) Uani 1 1 d . . .
C2 C 0.0900(5) 0.2135(2) 0.5744(3) 0.0376(8) Uani 1 1 d . . .
C3 C 0.0992(3) 0.13216(17) 0.5067(3) 0.0254(6) Uani 1 1 d . . .
N11 N 0.2724(4) 0.46552(17) 0.3544(3) 0.0296(6) Uani 1 1 d . . .
C11 C 0.1323(4) 0.51427(18) 0.3111(4) 0.0308(7) Uani 1 1 d . . .
C12 C 0.0000 0.4638(2) 0.2500 0.0298(9) Uani 1 2 d S . .
H1 H 0.163(5) 0.209(2) 0.662(5) 0.069(13) Uiso 1 1 d . . .
H2 H -0.034(5) 0.225(2) 0.604(5) 0.065(13) Uiso 1 1 d . . .
H11 H 0.251(5) 0.427(2) 0.412(4) 0.049(11) Uiso 1 1 d . . .
H12 H 0.337(5) 0.495(3) 0.388(4) 0.050(12) Uiso 1 1 d . . .
H13 H 0.319(5) 0.445(2) 0.283(4) 0.039(10) Uiso 1 1 d . . .
H14 H 0.100(4) 0.5405(19) 0.391(4) 0.036(9) Uiso 1 1 d . . .
H15 H 0.166(4) 0.552(2) 0.248(4) 0.039(9) Uiso 1 1 d . . .
H16 H 0.045(4) 0.432(2) 0.177(4) 0.047(10) Uiso 1 1 d . . .

loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_23
_atom_site_aniso_U_13
_atom_site_aniso_U_12
Cu1 0.0788(5) 0.0193(3) 0.0396(4) 0.000 -0.0355(3) 0.000
O1 0.120(3) 0.0278(12) 0.0388(14) 0.0062(11) -0.0363(15) -0.0220(14)
O2 0.0455(14) 0.0258(10) 0.0246(11) 0.0002(8) -0.0079(9) 0.0071(9)
O3 0.076(2) 0.0481(14) 0.0362(13) -0.0106(11) -0.0019(13) -0.0332(13)
O4 0.0503(16) 0.0387(12) 0.0306(12) 0.0120(10) -0.0038(10) 0.0018(11)
C1 0.043(2) 0.0320(16) 0.0301(16) -0.0058(13) -0.0023(14) -0.0056(14)
C2 0.047(2) 0.0383(17) 0.0272(17) -0.0042(14) 0.0041(15) -0.0091(16)
C3 0.0188(15) 0.0306(14) 0.0268(15) 0.0034(12) 0.0004(12) -0.0013(11)
N11 0.0268(16) 0.0303(14) 0.0316(14) -0.0069(13) -0.0030(12) -0.0015(12)
C11 0.0280(18) 0.0280(15) 0.0365(17) -0.0050(14) -0.0053(14) 0.0016(12)
C12 0.028(2) 0.0267(19) 0.035(2) 0.000 -0.001(2) 0.000

_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 1.9102(19) 4 ?
Cu1 O2 1.9102(19) . ?
Cu1 O1 1.919(2) . ?
Cu1 O1 1.919(2) 4 ?
O1 C1 1.262(4) . ?
O2 C3 1.268(3) . ?
O3 C1 1.231(4) . ?
O4 C3 1.238(3) . ?
C1 C2 1.507(4) . ?
C2 C3 1.521(4) . ?
N11 C11 1.480(4) . ?
C11 C12 1.504(4) . ?
C12 C11 1.504(4) 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
O2 Cu1 O2 89.09(12) 4 . ?
O2 Cu1 O1 170.89(13) 4 . ?
O2 Cu1 O1 92.01(9) . . ?
O2 Cu1 O1 92.01(9) 4 4 ?
O2 Cu1 O1 170.89(13) . 4 ?
O1 Cu1 O1 88.32(15) . 4 ?
C1 O1 Cu1 126.6(2) . . ?
C3 O2 Cu1 125.68(19) . . ?
O3 C1 O1 122.2(3) . . ?
O3 C1 C2 118.0(3) . . ?
O1 C1 C2 119.8(3) . . ?
C1 C2 C3 117.8(3) . . ?
O4 C3 O2 121.1(3) . . ?
O4 C3 C2 118.5(3) . . ?
O2 C3 C2 120.3(3) . . ?
N11 C11 C12 111.0(2) . . ?
C11 C12 C11 110.7(3) . 4 ?

_diffrn_measured_fraction_theta_max 0.930
_diffrn_reflns_theta_full        27.50
_diffrn_measured_fraction_theta_full 0.930
_refine_diff_density_max         0.297
_refine_diff_density_min         -0.580
_refine_diff_density_rms         0.070

# Attachment 'compound5.cif'

data_compound5
_database_code_depnum_ccdc_archive 'CCDC 253066'

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C10 H22 Cu N2 O10'
_chemical_formula_weight         393.84

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'
Cu Cu 0.3201 1.2651 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_H-M   'P 21'
_symmetry_space_group_name_Hall  'P 2yb'
_symmetry_Int_Tables_number      4

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

_cell_length_a                   7.3346(3)
_cell_length_b                   13.6142(3)
_cell_length_c                   7.9365(3)
_cell_angle_alpha                90.00
_cell_angle_beta                 97.519(3)
_cell_angle_gamma                90.00
_cell_volume                     785.68(5)
_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       'rectangular prism'
_exptl_crystal_colour            blue
_exptl_crystal_size_max          0.24
_exptl_crystal_size_mid          0.19
_exptl_crystal_size_min          0.16
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.665
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             410
_exptl_absorpt_coefficient_mu    1.444
_exptl_absorpt_correction_type   Multi-scan
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   '(SADABS, Sheldrick, Bruker, 2000)'

_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  'horizonally mounted graphite crystal'
_diffrn_radiation_probe          x-ray
_diffrn_source                   'Enraf Nonius FR590'
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 9
_diffrn_measurement_device       '95mm CCD camera on \k-goniostat'
_diffrn_measurement_device_type  KappaCCD
_diffrn_measurement_method       'CCD rotation images, thick slices'
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            4412
_diffrn_reflns_av_R_equivalents  0.0177
_diffrn_reflns_av_sigmaI/netI    0.0506
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_l_min       -10
_diffrn_reflns_limit_l_max       7
_diffrn_reflns_theta_min         4.65
_diffrn_reflns_theta_max         27.50
_reflns_number_total             3146
_reflns_number_gt                2680
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'Collect (Nonius BV, 1997-2000)'
_computing_cell_refinement       'Dirax/lsq (Duisenberg & Schreurs, 1989-2000)'
_computing_data_reduction        'EvalCCD (Duisenberg & Schreurs 1990-2000)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1997)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    'Ortep-3 for Windows (Farrugia, 1997)'
_computing_publication_material  'WinGX publication routines (Farrugia, 1999)'

_refine_special_details          
;
Refinement of F^2^ against ALL reflections. The weighted R-factor wR and
goodness of fit S are based on F^2^, conventional R-factors R are based
on F, with F set to zero for negative F^2^. The threshold expression of
F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is
not relevant to the choice of reflections for refinement. R-factors based
on F^2^ 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/[\s^2^(Fo^2^)+(0.0460P)^2^+0.0294P] where P=(Fo^2^+2Fc^2^)/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_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0.611(15)
_refine_ls_number_reflns         3146
_refine_ls_number_parameters     209
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0504
_refine_ls_R_factor_gt           0.0367
_refine_ls_wR_factor_ref         0.0829
_refine_ls_wR_factor_gt          0.0786
_refine_ls_goodness_of_fit_ref   1.046
_refine_ls_restrained_S_all      1.046
_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 0.21333(5) 0.04440(4) 0.50510(5) 0.02024(12) Uani 1 1 d . . .
C1 C 0.3758(5) -0.1026(3) 0.7350(5) 0.0227(8) Uani 1 1 d . . .
C2 C 0.4790(5) -0.1359(3) 0.5954(5) 0.0261(9) Uani 1 1 d . . .
H1 H 0.5301 -0.2004 0.6243 0.031 Uiso 1 1 calc R . .
H2 H 0.5810 -0.0913 0.5893 0.031 Uiso 1 1 calc R . .
C3 C 0.3675(5) -0.1415(3) 0.4226(5) 0.0232(8) Uani 1 1 d . . .
O1 O 0.2789(4) -0.0258(2) 0.7159(3) 0.0284(6) Uani 1 1 d . . .
O2 O 0.2724(4) -0.06589(19) 0.3692(3) 0.0269(7) Uani 1 1 d . . .
O3 O 0.3886(4) -0.1515(2) 0.8707(4) 0.0406(8) Uani 1 1 d . . .
O4 O 0.3707(4) -0.2172(2) 0.3361(4) 0.0385(8) Uani 1 1 d . . .
C11 C 0.1232(5) 0.2437(3) 0.5838(5) 0.0222(8) Uani 1 1 d . . .
C12 C 0.0245(5) 0.2466(3) 0.4024(5) 0.0227(8) Uani 1 1 d . . .
H12 H -0.0907 0.2112 0.3991 0.027 Uiso 1 1 calc R . .
H11 H -0.0051 0.3144 0.3729 0.027 Uiso 1 1 calc R . .
C13 C 0.1306(5) 0.2039(3) 0.2684(5) 0.0204(8) Uani 1 1 d . . .
O11 O 0.1872(4) 0.16051(19) 0.6399(3) 0.0286(6) Uani 1 1 d . . .
O12 O 0.2176(4) 0.1238(2) 0.2997(3) 0.0269(7) Uani 1 1 d . . .
O13 O 0.1391(4) 0.3176(2) 0.6701(4) 0.0351(7) Uani 1 1 d . . .
O14 O 0.1304(4) 0.2480(2) 0.1338(4) 0.0347(7) Uani 1 1 d . . .
C21 C 0.5289(6) 0.1155(3) 0.0243(5) 0.0336(10) Uani 1 1 d . . .
H25 H 0.4533 0.0569 0.0229 0.040 Uiso 1 1 calc R . .
H24 H 0.5672 0.1327 0.1421 0.040 Uiso 1 1 calc R . .
C22 C 0.6959(5) 0.0924(3) -0.0580(5) 0.0282(9) Uani 1 1 d . . .
H27 H 0.7731 0.1503 -0.0552 0.034 Uiso 1 1 calc R . .
H26 H 0.6584 0.0754 -0.1762 0.034 Uiso 1 1 calc R . .
C23 C 0.8051(6) 0.0091(3) 0.0282(5) 0.0307(10) Uani 1 1 d . . .
H28 H 0.8339 0.0237 0.1484 0.037 Uiso 1 1 calc R . .
H29 H 0.7312 -0.0502 0.0171 0.037 Uiso 1 1 calc R . .
C24 C 0.9785(5) -0.0083(3) -0.0446(5) 0.0294(9) Uani 1 1 d . . .
H31 H 1.0556 0.0497 -0.0272 0.035 Uiso 1 1 calc R . .
H30 H 0.9502 -0.0189 -0.1660 0.035 Uiso 1 1 calc R . .
N21 N 0.4158(5) 0.1966(3) -0.0586(4) 0.0279(8) Uani 1 1 d . . .
H21 H 0.3184 0.2063 -0.0044 0.042 Uiso 1 1 calc R . .
H22 H 0.3783 0.1810 -0.1665 0.042 Uiso 1 1 calc R . .
H23 H 0.4827 0.2513 -0.0546 0.042 Uiso 1 1 calc R . .
N22 N 1.0822(4) -0.0952(2) 0.0343(4) 0.0263(7) Uani 1 1 d . . .
H34 H 1.1855 -0.1029 -0.0120 0.039 Uiso 1 1 calc R . .
H33 H 1.0132 -0.1489 0.0161 0.039 Uiso 1 1 calc R . .
H32 H 1.1097 -0.0855 0.1456 0.039 Uiso 1 1 calc R . .
O1W O -0.0832(4) -0.0033(2) 0.4808(4) 0.0376(7) Uani 1 1 d . . .
O2W O 0.6029(4) 0.1113(2) 0.4852(4) 0.0412(8) Uani 1 1 d . . .

loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_23
_atom_site_aniso_U_13
_atom_site_aniso_U_12
Cu1 0.0299(2) 0.01346(19) 0.01662(18) -0.0004(2) 0.00042(13) 0.0048(3)
C1 0.0213(18) 0.023(2) 0.022(2) 0.0030(16) -0.0023(15) 0.0002(16)
C2 0.0241(19) 0.025(2) 0.028(2) -0.0008(17) -0.0022(16) 0.0069(17)
C3 0.025(2) 0.021(2) 0.024(2) -0.0033(16) 0.0066(16) 0.0014(17)
O1 0.0400(16) 0.0241(16) 0.0213(15) 0.0065(12) 0.0047(12) 0.0171(14)
O2 0.0444(17) 0.0163(16) 0.0180(15) -0.0050(12) -0.0028(13) 0.0096(13)
O3 0.0477(19) 0.038(2) 0.037(2) 0.0178(16) 0.0073(15) 0.0192(16)
O4 0.0567(19) 0.0232(16) 0.0348(18) -0.0083(13) 0.0031(14) 0.0131(14)
C11 0.028(2) 0.018(2) 0.022(2) -0.0018(15) 0.0061(15) 0.0023(16)
C12 0.0248(19) 0.0166(19) 0.026(2) 0.0042(15) -0.0002(16) 0.0046(16)
C13 0.0177(17) 0.024(2) 0.018(2) 0.0010(16) -0.0028(14) -0.0002(16)
O11 0.0481(17) 0.0133(15) 0.0223(16) -0.0021(11) -0.0039(13) 0.0098(13)
O12 0.0366(16) 0.0249(16) 0.0198(15) 0.0009(12) 0.0054(12) 0.0113(13)
O13 0.061(2) 0.0157(15) 0.0259(16) -0.0068(12) -0.0050(13) 0.0071(14)
O14 0.0447(17) 0.0377(19) 0.0231(16) 0.0134(14) 0.0098(13) 0.0164(15)
C21 0.036(2) 0.036(2) 0.028(2) 0.0046(19) 0.0055(18) 0.010(2)
C22 0.028(2) 0.027(2) 0.030(2) 0.0086(18) 0.0065(19) 0.0051(17)
C23 0.031(2) 0.033(3) 0.029(2) 0.0078(16) 0.0062(18) 0.0072(17)
C24 0.0279(19) 0.028(2) 0.033(2) 0.0027(18) 0.0063(17) 0.0073(18)
N21 0.0251(17) 0.0241(19) 0.033(2) -0.0048(15) -0.0020(15) -0.0003(16)
N22 0.0262(16) 0.0259(19) 0.0259(18) -0.0004(14) -0.0001(13) 0.0010(15)
O1W 0.0290(14) 0.0309(16) 0.051(2) -0.0079(15) -0.0011(14) -0.0017(13)
O2W 0.0367(17) 0.0377(17) 0.048(2) -0.0077(15) 0.0000(14) 0.0082(15)

_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(3) . ?
Cu1 O1 1.932(3) . ?
Cu1 O11 1.932(3) . ?
Cu1 O12 1.960(3) . ?
Cu1 O1W 2.254(3) . ?
C1 O3 1.258(5) . ?
C1 O1 1.263(5) . ?
C1 C2 1.491(5) . ?
C2 C3 1.504(5) . ?
C3 O4 1.241(5) . ?
C3 O2 1.284(5) . ?
C11 O13 1.215(5) . ?
C11 O11 1.283(4) . ?
C11 C12 1.525(5) . ?
C12 C13 1.514(5) . ?
C13 O14 1.225(4) . ?
C13 O12 1.271(5) . ?
C21 N21 1.483(5) . ?
C21 C22 1.495(6) . ?
C22 C23 1.500(5) . ?
C23 C24 1.483(5) . ?
C24 N22 1.499(5) . ?

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 92.91(11) . . ?
O2 Cu1 O11 172.42(13) . . ?
O1 Cu1 O11 87.50(12) . . ?
O2 Cu1 O12 86.28(12) . . ?
O1 Cu1 O12 164.56(13) . . ?
O11 Cu1 O12 91.31(12) . . ?
O2 Cu1 O1W 90.71(11) . . ?
O1 Cu1 O1W 93.41(12) . . ?
O11 Cu1 O1W 96.82(11) . . ?
O12 Cu1 O1W 102.02(12) . . ?
O3 C1 O1 121.2(4) . . ?
O3 C1 C2 119.1(3) . . ?
O1 C1 C2 119.6(3) . . ?
C1 C2 C3 115.1(3) . . ?
O4 C3 O2 122.2(4) . . ?
O4 C3 C2 119.9(3) . . ?
O2 C3 C2 117.9(3) . . ?
C1 O1 Cu1 125.9(3) . . ?
C3 O2 Cu1 126.2(2) . . ?
O13 C11 O11 122.1(4) . . ?
O13 C11 C12 120.6(3) . . ?
O11 C11 C12 117.3(3) . . ?
C13 C12 C11 115.4(3) . . ?
O14 C13 O12 122.3(4) . . ?
O14 C13 C12 118.8(3) . . ?
O12 C13 C12 118.9(3) . . ?
C11 O11 Cu1 126.0(3) . . ?
C13 O12 Cu1 125.0(2) . . ?
N21 C21 C22 113.9(4) . . ?
C21 C22 C23 112.2(3) . . ?
C24 C23 C22 112.1(3) . . ?
C23 C24 N22 112.2(3) . . ?

_diffrn_measured_fraction_theta_max 0.984
_diffrn_reflns_theta_full        27.50
_diffrn_measured_fraction_theta_full 0.984
_refine_diff_density_max         0.428
_refine_diff_density_min         -0.388
_refine_diff_density_rms         0.079


data_compound1b
_database_code_depnum_ccdc_archive 'CCDC 601070'

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C6 H12 Cu N2 O8'
_chemical_formula_weight         303.72

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'
Cu Cu 0.3201 1.2651 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_H-M   'F d d 2'
_symmetry_space_group_name_Hall  'F 2 -2 d'
_symmetry_Int_Tables_number      43

loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, z'
'-x+1/4, y+1/4, z+1/4'
'x+3/4, -y+3/4, z+1/4'
'x, y+1/2, z+1/2'
'-x, -y+1/2, z+1/2'
'-x+1/4, y+3/4, z+3/4'
'x+3/4, -y+5/4, z+3/4'
'x+1/2, y, z+1/2'
'-x+1/2, -y, z+1/2'
'-x+3/4, y+1/4, z+3/4'
'x+5/4, -y+3/4, z+3/4'
'x+1/2, y+1/2, z'
'-x+1/2, -y+1/2, z'
'-x+3/4, y+3/4, z+1/4'
'x+5/4, -y+5/4, z+1/4'

_cell_length_a                   13.6559(18)
_cell_length_b                   16.4436(9)
_cell_length_c                   9.0876(9)
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_volume                     2040.6(4)
_cell_formula_units_Z            8
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    ?
_cell_measurement_theta_min      ?
_cell_measurement_theta_max      ?

_exptl_crystal_description       'irregular prism'
_exptl_crystal_colour            'palid blue'
_exptl_crystal_size_max          0.12
_exptl_crystal_size_mid          0.12
_exptl_crystal_size_min          0.06
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.977
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1240
_exptl_absorpt_coefficient_mu    2.178
_exptl_absorpt_correction_type   Multi-scan
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   '(SADABS, Sheldrick, Bruker, 2000)'

_exptl_special_details           
;
?
;

_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           Mok\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  'horizonally mounted graphite crystal'
_diffrn_radiation_probe          x-ray
_diffrn_source                   'Enraf Nonius FR590'
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 9
_diffrn_measurement_device       '95mm CCD camera on \k-goniostat'
_diffrn_measurement_device_type  KappaCCD
_diffrn_measurement_method       'CCD rotation images, thick slices'
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            2259
_diffrn_reflns_av_R_equivalents  0.0202
_diffrn_reflns_av_sigmaI/netI    0.0408
_diffrn_reflns_limit_h_min       -17
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_k_max       21
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_limit_l_max       10
_diffrn_reflns_theta_min         5.13
_diffrn_reflns_theta_max         27.50
_reflns_number_total             1076
_reflns_number_gt                1009
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'Collect (Nonius BV, 1997-2000)'
_computing_cell_refinement       'Dirax/lsq (Duisenberg & Schreurs, 1989-2000)'
_computing_data_reduction        'EvalCCD (Duisenberg & Schreurs 1990-2000)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1997)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    'Ortep-3 for Windows (Farrugia, 1997)'
_computing_publication_material  'WinGX publication routines (Farrugia, 1999)'

_refine_special_details          
;
Refinement of F^2^ against ALL reflections. The weighted R-factor wR and
goodness of fit S are based on F^2^, conventional R-factors R are based
on F, with F set to zero for negative F^2^. The threshold expression of
F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is
not relevant to the choice of reflections for refinement. R-factors based
on F^2^ 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/[\s^2^(Fo^2^)+(0.0153P)^2^+2.0844P] where P=(Fo^2^+2Fc^2^)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0.03(2)
_refine_ls_number_reflns         1076
_refine_ls_number_parameters     103
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0261
_refine_ls_R_factor_gt           0.0226
_refine_ls_wR_factor_ref         0.0508
_refine_ls_wR_factor_gt          0.0499
_refine_ls_goodness_of_fit_ref   1.080
_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 0.2500 -0.2500 0.43896(8) 0.00639(11) Uani 1 2 d S . .
O1 O 0.21240(17) -0.17355(13) 0.2837(2) 0.0094(4) Uani 1 1 d . . .
O2 O 0.21161(17) -0.17521(13) 0.59398(18) 0.0088(4) Uani 1 1 d . . .
O3 O 0.13812(14) -0.06293(11) 0.2044(2) 0.0083(4) Uani 1 1 d . . .
O4 O 0.16410(12) -0.05815(10) 0.6902(3) 0.0085(4) Uani 1 1 d . . .
C1 C 0.1857(2) -0.10092(19) 0.3011(3) 0.0074(6) Uani 1 1 d . . .
C2 C 0.2137(2) -0.05474(15) 0.4397(4) 0.0076(5) Uani 1 1 d . . .
C3 C 0.1946(2) -0.09963(19) 0.5834(3) 0.0063(6) Uani 1 1 d . . .
N11 N 0.17996(17) -0.15024(13) -0.0555(4) 0.0093(4) Uani 1 1 d . . .
H11 H 0.161(3) -0.123(3) 0.031(5) 0.038(13) Uiso 1 1 d . . .
H12 H 0.148(2) -0.200(2) -0.068(5) 0.027(9) Uiso 1 1 d . . .
H13 H 0.171(3) -0.121(3) -0.136(5) 0.028(12) Uiso 1 1 d . . .
H14 H 0.245(2) -0.1608(17) -0.036(4) 0.009(8) Uiso 1 1 d . . .
H1 H 0.185(2) -0.0033(15) 0.442(3) 0.005(7) Uiso 1 1 d . . .
H2 H 0.283(2) -0.0460(17) 0.429(6) 0.008(7) Uiso 1 1 d . . .

loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_23
_atom_site_aniso_U_13
_atom_site_aniso_U_12
Cu1 0.00982(19) 0.00514(18) 0.00420(17) 0.000 0.000 0.0017(2)
O1 0.0141(11) 0.0073(11) 0.0068(10) -0.0001(8) 0.0003(9) 0.0031(10)
O2 0.0129(11) 0.0066(11) 0.0069(10) 0.0006(8) 0.0013(9) 0.0019(10)
O3 0.0095(9) 0.0106(9) 0.0050(10) 0.0014(10) 0.0005(9) 0.0040(7)
O4 0.0108(9) 0.0084(8) 0.0063(8) -0.0006(10) -0.0003(10) 0.0018(7)
C1 0.0046(13) 0.0089(15) 0.0086(14) -0.0002(12) 0.0037(12) -0.0017(12)
C2 0.0106(11) 0.0047(11) 0.0076(11) 0.0010(14) -0.0007(16) -0.0012(10)
C3 0.0042(14) 0.0091(15) 0.0055(13) 0.0000(11) -0.0014(11) -0.0032(12)
N11 0.0109(11) 0.0097(10) 0.0073(11) 0.0023(12) 0.0001(12) -0.0019(10)

_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 1.942(2) 14_545 ?
Cu1 O2 1.942(2) . ?
Cu1 O1 1.958(2) 14_545 ?
Cu1 O1 1.958(2) . ?
Cu1 O4 2.4365(17) 12_444 ?
Cu1 O4 2.4365(17) 7_544 ?
O1 C1 1.259(3) . ?
O2 C3 1.268(4) . ?
O3 C1 1.259(4) . ?
O4 C3 1.257(4) . ?
O4 Cu1 2.4365(17) 3 ?
C1 C2 1.519(4) . ?
C2 C3 1.523(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
O2 Cu1 O2 87.00(12) 14_545 . ?
O2 Cu1 O1 92.60(6) 14_545 14_545 ?
O2 Cu1 O1 179.27(11) . 14_545 ?
O2 Cu1 O1 179.27(11) 14_545 . ?
O2 Cu1 O1 92.60(6) . . ?
O1 Cu1 O1 87.81(12) 14_545 . ?
O2 Cu1 O4 89.82(8) 14_545 12_444 ?
O2 Cu1 O4 89.80(9) . 12_444 ?
O1 Cu1 O4 90.81(9) 14_545 12_444 ?
O1 Cu1 O4 89.57(9) . 12_444 ?
O2 Cu1 O4 89.80(9) 14_545 7_544 ?
O2 Cu1 O4 89.82(8) . 7_544 ?
O1 Cu1 O4 89.57(9) 14_545 7_544 ?
O1 Cu1 O4 90.81(9) . 7_544 ?
O4 Cu1 O4 179.47(13) 12_444 7_544 ?
C1 O1 Cu1 126.48(18) . . ?
C3 O2 Cu1 127.95(17) . . ?
C3 O4 Cu1 120.93(19) . 3 ?
O3 C1 O1 122.2(3) . . ?
O3 C1 C2 117.4(3) . . ?
O1 C1 C2 120.4(2) . . ?
C1 C2 C3 115.2(2) . . ?
O4 C3 O2 122.3(3) . . ?
O4 C3 C2 117.1(3) . . ?
O2 C3 C2 120.6(2) . . ?

_diffrn_measured_fraction_theta_max 0.992
_diffrn_reflns_theta_full        27.50
_diffrn_measured_fraction_theta_full 0.992
_refine_diff_density_max         0.328
_refine_diff_density_min         -0.359
_refine_diff_density_rms         0.076

