Electronic Supplementary Material for CrystEngComm
This journal is (c) The Royal SOciety of Chemistry 2007

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              
;
Crystal Engineering of 3D Coordination Polymers by
Pillaring Ferromagnetic Copper(II)-Methylmalonate Layers
;
loop_
_publ_author_name
'Catalina Ruiz-Perez'
'Miguel Julve'
'F. Lloret'
'Jorge Pasan'
'Joaquin Sanchiz'

data_compound-1
_database_code_depnum_ccdc_archive 'CCDC 635165'

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C4 H6 Cu O5'
_chemical_formula_weight         197.61

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'
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   Pn21m

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

_cell_length_a                   6.203(3)
_cell_length_b                   6.7961(12)
_cell_length_c                   6.998(2)
_cell_angle_alpha                90.000(17)
_cell_angle_beta                 90.00(3)
_cell_angle_gamma                90.00(3)
_cell_volume                     295.01(17)
_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       Prisms
_exptl_crystal_colour            Blue
_exptl_crystal_size_max          0.1
_exptl_crystal_size_mid          0.1
_exptl_crystal_size_min          0.18
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    2.022
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             178
_exptl_absorpt_coefficient_mu    3.633
_exptl_absorpt_correction_type   sadabs
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   ?

_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            1821
_diffrn_reflns_av_R_equivalents  0.0456
_diffrn_reflns_av_sigmaI/netI    0.0480
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_l_min       -6
_diffrn_reflns_limit_l_max       9
_diffrn_reflns_theta_min         5.32
_diffrn_reflns_theta_max         27.49
_reflns_number_total             687
_reflns_number_gt                638
_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    CRYSTALMAKER
_computing_publication_material  'PARST97 (Nardelli, 1997)'

_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^)+(0.0439P)^2^+0.2720P] 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   0.51(4)
_refine_ls_number_reflns         687
_refine_ls_number_parameters     66
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0385
_refine_ls_R_factor_gt           0.0352
_refine_ls_wR_factor_ref         0.0872
_refine_ls_wR_factor_gt          0.0862
_refine_ls_goodness_of_fit_ref   1.090
_refine_ls_restrained_S_all      1.089
_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 0.9483(5) 0.3641(6) 0.1965(5) 0.0324(9) Uani 1 1 d . . .
O1W O 0.8021(10) -0.0175(9) 0.0000 0.0339(12) Uani 1 2 d S . .
O2 O 0.7320(5) 0.5993(5) 0.2975(5) 0.0290(8) Uani 1 1 d . . .
C1 C 0.7844(7) 0.4714(7) 0.1772(7) 0.0240(9) Uani 1 1 d . . .
C2 C 0.6408(11) 0.4456(10) 0.0000 0.0248(13) Uani 1 2 d S . .
C3 C 0.4427(12) 0.5764(12) 0.0000 0.0303(16) Uani 1 2 d S . .
H2 H 0.593(10) 0.299(14) 0.0000 0.03(2) Uiso 1 2 d S . .
H3A H 0.472(9) 0.688(19) 0.0000 0.013(15) Uiso 1 2 d S . .
H3B H 0.363(8) 0.556(8) 0.106(7) 0.019(12) Uiso 1 1 d . . .
H1W H 1.195(12) 0.438(11) 0.413(9) 0.05(3) Uiso 1 1 d . . .
Cu1 Cu 1.07493(10) 0.1964 0.0000 0.0233(2) Uani 1 2 d S . .

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
O1 0.042(2) 0.035(2) 0.0209(16) -0.0038(14) -0.0050(14) 0.0082(16)
O1W 0.048(3) 0.026(3) 0.028(3) 0.000 0.000 -0.003(2)
O2 0.0348(17) 0.0289(19) 0.0232(16) -0.0058(13) -0.0009(15) 0.0004(14)
C1 0.031(2) 0.024(2) 0.017(2) 0.0001(18) 0.0047(18) -0.0060(19)
C2 0.027(3) 0.025(3) 0.022(3) 0.000 0.000 -0.002(3)
C3 0.030(4) 0.032(4) 0.029(4) 0.000 0.000 -0.004(3)
Cu1 0.0322(4) 0.0192(3) 0.0184(3) 0.000 0.000 -0.0014(5)

_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 C1 1.258(6) . ?
O1 Cu1 1.951(4) . ?
O1W Cu1 2.231(6) . ?
O2 C1 1.252(6) . ?
O2 Cu1 1.970(3) 3_755 ?
C1 C2 1.537(6) . ?
C2 C3 1.517(11) . ?
C2 C1 1.537(6) 2 ?
Cu1 O1 1.951(4) 2 ?
Cu1 O2 1.970(3) 4_745 ?
Cu1 O2 1.970(3) 3_744 ?

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
C1 O1 Cu1 126.1(3) . . ?
C1 O2 Cu1 123.9(3) . 3_755 ?
O2 C1 O1 122.7(4) . . ?
O2 C1 C2 118.1(5) . . ?
O1 C1 C2 119.2(5) . . ?
C3 C2 C1 113.7(4) . . ?
C3 C2 C1 113.7(4) . 2 ?
C1 C2 C1 107.6(5) . 2 ?
O1 Cu1 O1 89.6(2) . 2 ?
O1 Cu1 O2 86.19(15) . 4_745 ?
O1 Cu1 O2 161.39(14) 2 4_745 ?
O1 Cu1 O2 161.39(14) . 3_744 ?
O1 Cu1 O2 86.19(15) 2 3_744 ?
O2 Cu1 O2 92.0(2) 4_745 3_744 ?
O1 Cu1 O1W 94.31(16) . . ?
O1 Cu1 O1W 94.31(16) 2 . ?
O2 Cu1 O1W 104.06(15) 4_745 . ?
O2 Cu1 O1W 104.06(15) 3_744 . ?

_diffrn_measured_fraction_theta_max 0.990
_diffrn_reflns_theta_full        27.49
_diffrn_measured_fraction_theta_full 0.990
_refine_diff_density_max         0.489
_refine_diff_density_min         -0.842
_refine_diff_density_rms         0.086

data_compound2
_database_code_depnum_ccdc_archive 'CCDC 635166'

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C6 H6 Cu N O4'
_chemical_formula_weight         219.66

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   P21/n

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

_cell_length_a                   6.2854(2)
_cell_length_b                   16.4373(6)
_cell_length_c                   7.0129(2)
_cell_angle_alpha                90.00
_cell_angle_beta                 92.594(2)
_cell_angle_gamma                90.00
_cell_volume                     723.80(4)
_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       Prisms
_exptl_crystal_colour            Blue
_exptl_crystal_size_max          0.56
_exptl_crystal_size_mid          0.44
_exptl_crystal_size_min          0.08
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    2.016
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             440
_exptl_absorpt_coefficient_mu    2.986
_exptl_absorpt_correction_type   none
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   ?

_exptl_special_details           
;
?
;

_diffrn_ambient_temperature      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            4780
_diffrn_reflns_av_R_equivalents  0.0273
_diffrn_reflns_av_sigmaI/netI    0.0302
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_h_max       5
_diffrn_reflns_limit_k_min       -19
_diffrn_reflns_limit_k_max       21
_diffrn_reflns_limit_l_min       -8
_diffrn_reflns_limit_l_max       9
_diffrn_reflns_theta_min         4.08
_diffrn_reflns_theta_max         27.49
_reflns_number_total             1590
_reflns_number_gt                1381
_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    CRYSTALMAKER
_computing_publication_material  'PARST97 (Nardelli, 1997)'

_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           fullcycle
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[\s^2^(Fo^2^)+(0.0258P)^2^+1.3627P] 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_number_reflns         1590
_refine_ls_number_parameters     138
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0382
_refine_ls_R_factor_gt           0.0300
_refine_ls_wR_factor_ref         0.0738
_refine_ls_wR_factor_gt          0.0704
_refine_ls_goodness_of_fit_ref   0.906
_refine_ls_restrained_S_all      0.906
_refine_ls_shift/su_max          1.166
_refine_ls_shift/su_mean         0.208

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 0.18444(6) 0.31124(2) 0.96194(5) 0.01699(13) Uani 1 1 d . . .
O3 O 0.0125(3) 0.36151(12) 0.7539(3) 0.0220(4) Uani 1 1 d . . .
O1 O -0.0011(3) 0.35304(13) 1.1564(3) 0.0232(5) Uani 1 1 d . . .
O4 O 0.3524(3) 0.25223(13) 1.1596(3) 0.0240(5) Uani 1 1 d . . .
O2 O 0.3569(4) 0.25996(13) 0.7676(3) 0.0235(5) Uani 1 1 d . . .
C1 C -0.0986(5) 0.31454(17) 1.2782(4) 0.0176(6) Uani 1 1 d . . .
C3 C -0.0951(4) 0.32054(17) 0.6335(4) 0.0175(6) Uani 1 1 d . . .
C5 C 0.3012(5) 0.49891(19) 1.0558(5) 0.0226(6) Uani 1 1 d . . .
N1 N 0.3791(4) 0.42879(15) 0.9933(4) 0.0200(5) Uani 1 1 d . . .
C6 C 0.5791(5) 0.4308(2) 0.9379(5) 0.0228(6) Uani 1 1 d . . .
H5 H 0.845(6) 0.505(2) 0.901(5) 0.023(9) Uiso 1 1 d . . .
H6 H 0.643(6) 0.384(2) 0.911(5) 0.020(8) Uiso 1 1 d . . .
C2A C -0.1870(8) 0.3600(3) 1.4481(6) 0.0232(15) Uani 0.541(9) 1 d P . 1
H2A H -0.1047 0.4106 1.4460 0.10(4) Uiso 0.541(9) 1 calc PR . 1
C4A C -0.3873(8) 0.3891(3) 1.4464(6) 0.042(2) Uani 0.541(9) 1 d PR . 1
H41A H -0.4563 0.3794 1.3236 0.16(4) Uiso 0.541(9) 1 calc PR . 1
H42A H -0.3837 0.4466 1.4713 0.18(5) Uiso 0.541(9) 1 calc PR . 1
H43A H -0.4647 0.3622 1.5430 0.16(5) Uiso 0.541(9) 1 calc PR . 1
C2B C -0.1451(10) 0.3678(3) 1.4508(7) 0.0243(19) Uani 0.459(9) 1 d P . 2
H2B H -0.2998 0.3599 1.4466 0.13(4) Uiso 0.459(9) 1 calc PR . 2
C4B C -0.1467(10) 0.4481(3) 1.4397(7) 0.048(3) Uani 0.459(9) 1 d PR . 2
H41B H -0.1252 0.4644 1.3105 0.12(4) Uiso 0.459(9) 1 calc PR . 2
H42B H -0.0347 0.4699 1.5222 0.12(5) Uiso 0.459(9) 1 calc PR . 2
H43B H -0.2815 0.4683 1.4783 0.27(7) Uiso 0.459(9) 1 calc PR . 2

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 0.01717(19) 0.01827(19) 0.0156(2) -0.00098(13) 0.00209(13) 0.00158(14)
O3 0.0262(11) 0.0187(10) 0.0209(11) -0.0022(8) -0.0018(9) 0.0025(9)
O1 0.0267(11) 0.0209(10) 0.0228(11) 0.0045(8) 0.0108(9) 0.0035(9)
O4 0.0282(12) 0.0254(11) 0.0181(10) -0.0058(8) -0.0029(9) 0.0060(9)
O2 0.0278(11) 0.0227(11) 0.0206(10) 0.0029(8) 0.0068(9) 0.0070(9)
C1 0.0166(13) 0.0222(14) 0.0139(13) -0.0006(11) 0.0005(11) 0.0041(11)
C3 0.0166(13) 0.0213(14) 0.0146(13) 0.0012(11) 0.0028(11) 0.0042(11)
C5 0.0164(13) 0.0240(15) 0.0276(16) -0.0028(12) 0.0041(12) -0.0005(12)
N1 0.0184(11) 0.0205(12) 0.0212(13) -0.0003(10) 0.0018(10) -0.0018(10)
C6 0.0204(14) 0.0225(15) 0.0257(16) -0.0036(12) 0.0050(12) 0.0023(12)
C2A 0.036(3) 0.017(3) 0.017(3) 0.000(2) 0.006(2) 0.006(2)
C4A 0.046(4) 0.060(5) 0.020(3) -0.007(3) -0.003(3) 0.037(4)
C2B 0.028(4) 0.032(4) 0.013(3) -0.003(3) 0.001(3) 0.005(3)
C4B 0.104(9) 0.018(4) 0.022(4) 0.001(3) 0.012(5) 0.009(5)

_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 1.958(2) . ?
Cu1 O3 1.959(2) . ?
Cu1 O4 1.961(2) . ?
Cu1 O2 1.969(2) . ?
Cu1 N1 2.292(3) . ?
O3 C3 1.254(4) . ?
O1 C1 1.246(4) . ?
O4 C3 1.256(4) 4_666 ?
O2 C1 1.258(4) 4_665 ?
C1 O2 1.258(4) 4_566 ?
C1 C2A 1.532(6) . ?
C1 C2B 1.532(5) . ?
C3 O4 1.256(4) 4_565 ?
C3 C2B 1.519(5) 1_554 ?
C3 C2A 1.542(6) 1_554 ?
C5 N1 1.334(4) . ?
C5 C6 1.379(5) 3_667 ?
N1 C6 1.333(4) . ?
C6 C5 1.379(5) 3_667 ?
C2A C4A 1.3461 . ?
C2A C3 1.542(6) 1_556 ?
C2B C4B 1.3226 . ?
C2B C3 1.519(5) 1_556 ?

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 O3 92.59(10) . . ?
O1 Cu1 O4 89.98(10) . . ?
O3 Cu1 O4 175.25(9) . . ?
O1 Cu1 O2 174.87(10) . . ?
O3 Cu1 O2 88.14(9) . . ?
O4 Cu1 O2 88.96(9) . . ?
O1 Cu1 N1 88.26(10) . . ?
O3 Cu1 N1 89.43(10) . . ?
O4 Cu1 N1 94.65(10) . . ?
O2 Cu1 N1 96.83(10) . . ?
C3 O3 Cu1 122.5(2) . . ?
C1 O1 Cu1 128.8(2) . . ?
C3 O4 Cu1 120.3(2) 4_666 . ?
C1 O2 Cu1 120.3(2) 4_665 . ?
O1 C1 O2 124.7(3) . 4_566 ?
O1 C1 C2A 119.5(3) . . ?
O2 C1 C2A 115.7(3) 4_566 . ?
O1 C1 C2B 111.6(2) . . ?
O2 C1 C2B 123.6(2) 4_566 . ?
C2A C1 C2B 10.9(2) . . ?
O3 C3 O4 123.4(3) . 4_565 ?
O3 C3 C2B 112.2(2) . 1_554 ?
O4 C3 C2B 124.4(3) 4_565 1_554 ?
O3 C3 C2A 120.8(3) . 1_554 ?
O4 C3 C2A 115.7(3) 4_565 1_554 ?
C2B C3 C2A 10.9(3) 1_554 1_554 ?
N1 C5 C6 121.8(3) . 3_667 ?
C5 N1 C6 116.1(3) . . ?
C5 N1 Cu1 123.9(2) . . ?
C6 N1 Cu1 119.9(2) . . ?
N1 C6 C5 122.1(3) . 3_667 ?
C4A C2A C1 122.6(2) . . ?
C4A C2A C3 118.1(2) . 1_556 ?
C1 C2A C3 108.4(3) . 1_556 ?
C4B C2B C3 124.1(2) . 1_556 ?
C4B C2B C1 121.7(2) . . ?
C3 C2B C1 109.6(3) 1_556 . ?

_diffrn_measured_fraction_theta_max 0.958
_diffrn_reflns_theta_full        27.49
_diffrn_measured_fraction_theta_full 0.958
_refine_diff_density_max         0.411
_refine_diff_density_min         -0.439
_refine_diff_density_rms         0.088


# Attachment 'compound3.cif'

data_compound-3
_database_code_depnum_ccdc_archive 'CCDC 635167'

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C9 H10 Cu N O5'
_chemical_formula_weight         275.72

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           Monoclinic
_symmetry_space_group_name_H-M   P21/n

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

_cell_length_a                   7.2395(4)
_cell_length_b                   19.4035(14)
_cell_length_c                   7.3889(3)
_cell_angle_alpha                90.000(5)
_cell_angle_beta                 91.844(5)
_cell_angle_gamma                90.000(5)
_cell_volume                     1037.39(10)
_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       Sheets
_exptl_crystal_colour            Blue
_exptl_crystal_size_max          0.08
_exptl_crystal_size_mid          0.08
_exptl_crystal_size_min          0.04
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.765
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             560
_exptl_absorpt_coefficient_mu    2.110
_exptl_absorpt_correction_type   sadabs
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   ?

_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            6209
_diffrn_reflns_av_R_equivalents  0.0475
_diffrn_reflns_av_sigmaI/netI    0.0732
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_k_min       -25
_diffrn_reflns_limit_k_max       21
_diffrn_reflns_limit_l_min       -9
_diffrn_reflns_limit_l_max       9
_diffrn_reflns_theta_min         6.45
_diffrn_reflns_theta_max         27.49
_reflns_number_total             2297
_reflns_number_gt                1708
_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    CRYSTALMAKER
_computing_publication_material  'PARST97 (Nardelli, 1997)'

_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^)+(0.0185P)^2^+6.8543P] 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_number_reflns         2297
_refine_ls_number_parameters     169
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0921
_refine_ls_R_factor_gt           0.0597
_refine_ls_wR_factor_ref         0.1145
_refine_ls_wR_factor_gt          0.1035
_refine_ls_goodness_of_fit_ref   1.052
_refine_ls_restrained_S_all      1.052
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C 0.3031(10) 0.3222(3) 0.7342(7) 0.0322(15) Uani 1 1 d . . .
C2 C 0.4745(11) 0.3644(3) 0.6900(9) 0.0366(17) Uani 1 1 d . . .
C3 C 0.6469(10) 0.3220(3) 0.7374(7) 0.0307(15) Uani 1 1 d . . .
C4 C 0.4786(17) 0.4350(4) 0.7756(11) 0.054(2) Uani 1 1 d . . .
C5 C 0.531(2) 0.0739(4) 0.6374(12) 0.105(5) Uani 1 1 d . . .
H5 H 0.5590 0.0658 0.5174 0.126 Uiso 1 1 calc R . .
C6 C 0.538(2) 0.0188(4) 0.7542(11) 0.113(5) Uani 1 1 d . . .
H4 H 0.5699 -0.0247 0.7127 0.136 Uiso 1 1 calc R . .
C7 C 0.4979(7) 0.0286(3) 0.9331(7) 0.0177(11) Uani 1 1 d . . .
C8 C 0.4667(10) 0.0951(3) 0.9830(9) 0.0341(15) Uani 1 1 d . . .
H2 H 0.4496 0.1058 1.1040 0.041 Uiso 1 1 calc R . .
C9 C 0.4606(9) 0.1465(3) 0.8544(7) 0.0277(14) Uani 1 1 d . . .
H1 H 0.4362 0.1912 0.8925 0.033 Uiso 1 1 calc R . .
Cu1 Cu 0.47499(7) 0.21292(3) 0.49562(8) 0.00899(17) Uani 1 1 d . . .
N1 N 0.4868(6) 0.1364(2) 0.6822(5) 0.0141(9) Uani 1 1 d . . .
O1 O 0.1989(6) 0.3431(2) 0.8556(5) 0.0353(11) Uani 1 1 d . . .
O2 O 0.2714(6) 0.2670(2) 0.6451(5) 0.0327(11) Uani 1 1 d . . .
O1W O 0.4765(8) 0.2843(2) 0.3041(5) 0.0203(8) Uani 1 1 d . . .
O3 O 0.7581(6) 0.3443(2) 0.8572(5) 0.0329(10) Uani 1 1 d . . .
O4 O 0.6719(6) 0.26651(19) 0.6510(5) 0.0306(10) Uani 1 1 d . . .
H1W H 0.563(11) 0.276(4) 0.252(11) 0.05(3) Uiso 1 1 d . . .
H2W H 0.398(10) 0.283(4) 0.259(10) 0.03(3) Uiso 1 1 d . . .
H10 H 0.557(15) 0.467(6) 0.718(15) 0.11(4) Uiso 1 1 d . . .
H11 H 0.365(9) 0.460(4) 0.735(9) 0.035(19) Uiso 1 1 d . . .
H12 H 0.481(8) 0.432(3) 0.909(11) 0.037(19) Uiso 1 1 d . . .
H13 H 0.470(10) 0.371(4) 0.577(11) 0.06(2) 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
C1 0.078(5) 0.011(3) 0.009(3) 0.004(2) 0.004(3) 0.003(3)
C2 0.091(5) 0.009(3) 0.011(3) 0.000(2) 0.010(3) -0.001(3)
C3 0.071(4) 0.011(3) 0.010(3) 0.003(2) 0.008(3) -0.013(3)
C4 0.127(8) 0.011(3) 0.024(4) -0.002(3) 0.010(5) 0.003(4)
C5 0.277(15) 0.016(4) 0.024(4) 0.009(3) 0.047(7) 0.028(6)
C6 0.305(17) 0.017(4) 0.022(4) 0.009(3) 0.055(7) 0.032(6)
C7 0.035(3) 0.012(2) 0.006(2) 0.004(2) 0.001(2) -0.001(2)
C8 0.073(4) 0.017(3) 0.014(3) 0.000(3) 0.012(3) 0.010(3)
C9 0.060(4) 0.015(3) 0.009(3) 0.002(2) 0.008(3) 0.014(3)
Cu1 0.0142(3) 0.0073(3) 0.0055(3) 0.0013(3) 0.00018(18) -0.0004(3)
N1 0.024(2) 0.011(2) 0.007(2) 0.0017(17) 0.0008(17) -0.0002(17)
O1 0.070(3) 0.023(2) 0.013(2) -0.0030(17) 0.001(2) 0.005(2)
O2 0.071(3) 0.015(2) 0.012(2) -0.0018(16) 0.0094(19) -0.0058(19)
O1W 0.038(3) 0.0138(19) 0.0093(19) 0.0001(17) 0.0013(19) 0.003(2)
O3 0.063(3) 0.020(2) 0.016(2) -0.0079(17) 0.0122(19) -0.018(2)
O4 0.070(3) 0.0101(19) 0.011(2) -0.0026(15) -0.0071(19) -0.0003(18)

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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
C1 O1 1.258(7) . ?
C1 O2 1.274(7) . ?
C1 C2 1.530(10) . ?
C2 C4 1.509(9) . ?
C2 C3 1.526(10) . ?
C3 O3 1.254(7) . ?
C3 O4 1.268(7) . ?
C5 N1 1.301(9) . ?
C5 C6 1.373(10) . ?
C6 C7 1.376(9) . ?
C7 C8 1.362(7) . ?
C7 C7 1.487(10) 3_657 ?
C8 C9 1.378(8) . ?
C9 N1 1.307(6) . ?
Cu1 O1W 1.980(4) . ?
Cu1 N1 2.025(4) . ?
Cu1 O4 2.080(4) . ?
Cu1 O2 2.144(4) . ?
Cu1 O3 2.154(5) 4_565 ?
Cu1 O1 2.234(5) 4_665 ?
O1 Cu1 2.234(5) 4_566 ?
O3 Cu1 2.154(5) 4_666 ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
O1 C1 O2 122.5(6) . . ?
O1 C1 C2 119.2(5) . . ?
O2 C1 C2 118.2(5) . . ?
C4 C2 C3 112.8(7) . . ?
C4 C2 C1 113.7(7) . . ?
C3 C2 C1 109.0(5) . . ?
O3 C3 O4 123.3(6) . . ?
O3 C3 C2 118.5(5) . . ?
O4 C3 C2 118.1(5) . . ?
N1 C5 C6 124.9(7) . . ?
C5 C6 C7 119.4(7) . . ?
C8 C7 C6 115.7(5) . . ?
C8 C7 C7 121.8(6) . 3_657 ?
C6 C7 C7 122.3(6) . 3_657 ?
C7 C8 C9 120.1(5) . . ?
N1 C9 C8 124.1(5) . . ?
O1W Cu1 N1 176.10(19) . . ?
O1W Cu1 O4 91.44(18) . . ?
N1 Cu1 O4 88.71(16) . . ?
O1W Cu1 O2 92.59(18) . . ?
N1 Cu1 O2 91.31(16) . . ?
O4 Cu1 O2 86.64(17) . . ?
O1W Cu1 O3 92.41(18) . 4_565 ?
N1 Cu1 O3 87.69(16) . 4_565 ?
O4 Cu1 O3 174.78(16) . 4_565 ?
O2 Cu1 O3 89.67(16) . 4_565 ?
O1W Cu1 O1 89.36(18) . 4_665 ?
N1 Cu1 O1 86.74(16) . 4_665 ?
O4 Cu1 O1 90.23(16) . 4_665 ?
O2 Cu1 O1 176.35(16) . 4_665 ?
O3 Cu1 O1 93.33(15) 4_565 4_665 ?
C5 N1 C9 115.6(5) . . ?
C5 N1 Cu1 121.1(4) . . ?
C9 N1 Cu1 123.3(4) . . ?
C1 O1 Cu1 129.3(4) . 4_566 ?
C1 O2 Cu1 124.2(4) . . ?
C3 O3 Cu1 126.8(4) . 4_666 ?
C3 O4 Cu1 126.6(4) . . ?

_diffrn_measured_fraction_theta_max 0.963
_diffrn_reflns_theta_full        27.49
_diffrn_measured_fraction_theta_full 0.963
_refine_diff_density_max         1.013
_refine_diff_density_min         -0.901
_refine_diff_density_rms         0.137


