# Electronic Supplementary Material for CrystEngComm
# This journal is (c) The Royal Society of Chemistry 2008

data_global
_journal_name_full               CrystEngComm

_journal_coden_Cambridge         1350

_publ_contact_author_name        'Yao-Yu Wang'
_publ_contact_author_email       WYAOYU@NWU.EDU.CN

_publ_section_title              
;
A Series of Intriguing Metal-Organic Frameworks with
3,3?,4,4?- Benzophenonetetracarboxylic Acid: Structural Adjustment and
pH-Dependent
;
loop_
_publ_author_name
'Yao-Yu Wang.'
'Stuart Batten'
'Qi-Zhen Shi.'
'Hong Wang.'
'Cui-Juan Wang.'
;
Gui-Lin Wen
;
'Guo-Ping Yang.'

# Attachment 'compound_2.cif'

data_2
_database_code_depnum_ccdc_archive 'CCDC 656397'

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C35 H37 Cu1.50 N3 O15'
_chemical_formula_weight         834.99

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cu Cu 0.3201 1.2651 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_symmetry_cell_setting           Triclinic
_symmetry_space_group_name_H-M   P-1

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

_cell_length_a                   10.2701(13)
_cell_length_b                   13.3741(17)
_cell_length_c                   14.9368(19)
_cell_angle_alpha                89.016(2)
_cell_angle_beta                 86.975(2)
_cell_angle_gamma                67.753(2)
_cell_volume                     1896.2(4)
_cell_formula_units_Z            2
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    2028
_cell_measurement_theta_min      2.48
_cell_measurement_theta_max      21.36

_exptl_crystal_description       prism
_exptl_crystal_colour            blue
_exptl_crystal_size_max          0.25
_exptl_crystal_size_mid          0.13
_exptl_crystal_size_min          0.07
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.462
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             863
_exptl_absorpt_coefficient_mu    0.922
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.7995
_exptl_absorpt_correction_T_max  0.9349
_exptl_absorpt_process_details   sadabs

_exptl_special_details           
;
?
;

_diffrn_ambient_temperature      293(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         0
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            14256
_diffrn_reflns_av_R_equivalents  0.0456
_diffrn_reflns_av_sigmaI/netI    0.0789
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_theta_min         2.48
_diffrn_reflns_theta_max         25.50
_reflns_number_total             7018
_reflns_number_gt                4540
_reflns_threshold_expression     >2sigma(I)

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

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

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.1246P)²+1.2367P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         7018
_refine_ls_number_parameters     494
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1061
_refine_ls_R_factor_gt           0.0660
_refine_ls_wR_factor_ref         0.2235
_refine_ls_wR_factor_gt          0.1916
_refine_ls_goodness_of_fit_ref   1.044
_refine_ls_restrained_S_all      1.044
_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 0.79392(7) 0.84381(5) -0.07801(5) 0.0299(2) Uani 1 1 d . . .
Cu2 Cu 1.0000 0.0000 0.5000 0.0533(4) Uani 1 2 d S . .
O1 O 0.6598(4) 0.8694(3) 0.0264(3) 0.0354(9) Uani 1 1 d . . .
O2 O 0.8275(4) 0.7534(4) 0.1074(3) 0.0502(12) Uani 1 1 d . . .
O3 O 0.6162(4) 1.0106(3) 0.2033(3) 0.0478(11) Uani 1 1 d . . .
O4 O 0.3945(4) 1.0917(3) 0.1676(3) 0.0432(11) Uani 1 1 d . . .
O5 O 0.3687(4) 0.5826(3) 0.2934(3) 0.0412(10) Uani 1 1 d . . .
O6 O 1.0296(4) 0.2120(3) 0.1517(3) 0.0321(9) Uani 1 1 d . . .
O7 O 1.0980(5) 0.1915(4) 0.2928(3) 0.0570(13) Uani 1 1 d . . .
O8 O 0.8400(4) 0.1143(3) 0.2498(3) 0.0423(10) Uani 1 1 d . . .
O9 O 0.6148(4) 0.1950(3) 0.2165(3) 0.0488(12) Uani 1 1 d . . .
H9D H 0.6238 0.1335 0.2029 0.073 Uiso 1 1 calc R . .
O10 O 0.9566(9) -0.0519(5) 0.3654(4) 0.134(3) Uani 1 1 d . . .
H1W H 1.0079 -0.1021 0.3290 0.202 Uiso 1 1 d R . .
H2W H 0.9230 -0.0007 0.3273 0.202 Uiso 1 1 d R . .
O11 O 1.1390(6) 0.0632(5) 0.4370(4) 0.099(2) Uani 1 1 d . . .
H3W H 1.2060 0.0062 0.4162 0.148 Uiso 1 1 d R . .
H4W H 1.1123 0.1056 0.3919 0.148 Uiso 1 1 d R . .
O12 O 0.3657(18) 0.0899(14) 0.4927(18) 0.422(17) Uani 1 1 d . . .
H5W H 0.3888 0.0384 0.4540 0.634 Uiso 1 1 d R . .
H6W H 0.3205 0.0839 0.5413 0.634 Uiso 1 1 d R . .
O13 O 0.3313(8) 0.2480(7) 0.3225(5) 0.118(3) Uani 1 1 d . . .
H7W H 0.4178 0.2320 0.3047 0.177 Uiso 1 1 d R . .
H8W H 0.2839 0.3058 0.2941 0.177 Uiso 1 1 d R . .
O14 O 0.1531(11) 0.5011(10) 0.3318(6) 0.181(5) Uani 1 1 d . . .
H9W H 0.2059 0.4383 0.3506 0.272 Uiso 1 1 d R . .
H10W H 0.2185 0.5257 0.3209 0.272 Uiso 1 1 d R . .
O15 O 0.9128(13) 0.7267(16) 0.2833(7) 0.305(10) Uani 1 1 d . . .
H11W H 0.8885 0.7356 0.2286 0.458 Uiso 1 1 d R . .
H12W H 0.9247 0.7818 0.3045 0.458 Uiso 1 1 d R . .
N1 N 0.7866(5) 0.6931(3) -0.0881(3) 0.0311(11) Uani 1 1 d . . .
N2 N 0.8090(5) -0.0119(3) -0.0635(3) 0.0291(10) Uani 1 1 d . . .
N3 N 0.8409(6) 0.1445(4) 0.4875(4) 0.0480(14) Uani 1 1 d . . .
C1 C 0.7026(6) 0.8113(4) 0.0948(4) 0.0338(13) Uani 1 1 d . . .
C2 C 0.4952(6) 1.0109(4) 0.1860(4) 0.0321(13) Uani 1 1 d . . .
C3 C 0.4792(6) 0.5930(4) 0.2721(4) 0.0305(12) Uani 1 1 d . . .
C4 C 0.5884(5) 0.8086(4) 0.1621(4) 0.0274(12) Uani 1 1 d . . .
C5 C 0.4830(5) 0.9023(4) 0.1981(4) 0.0291(12) Uani 1 1 d . . .
C6 C 0.3740(6) 0.8946(4) 0.2526(4) 0.0358(14) Uani 1 1 d . . .
H6 H 0.3022 0.9570 0.2746 0.043 Uiso 1 1 calc R . .
C7 C 0.3711(6) 0.7935(4) 0.2749(4) 0.0330(13) Uani 1 1 d . . .
H7 H 0.2968 0.7887 0.3107 0.040 Uiso 1 1 calc R . .
C8 C 0.4793(6) 0.7000(4) 0.2435(4) 0.0307(12) Uani 1 1 d . . .
C9 C 0.5845(6) 0.7090(4) 0.1854(4) 0.0337(13) Uani 1 1 d . . .
H9 H 0.6540 0.6466 0.1616 0.040 Uiso 1 1 calc R . .
C10 C 0.6158(6) 0.4973(4) 0.2725(4) 0.0301(12) Uani 1 1 d . . .
C11 C 0.6138(6) 0.3959(4) 0.2567(4) 0.0290(12) Uani 1 1 d . . .
H11A H 0.5281 0.3885 0.2510 0.035 Uiso 1 1 calc R . .
C12 C 0.7393(5) 0.3043(4) 0.2492(3) 0.0268(12) Uani 1 1 d . . .
C13 C 0.8670(6) 0.3173(4) 0.2596(4) 0.0291(12) Uani 1 1 d . . .
C14 C 0.8666(6) 0.4165(4) 0.2826(4) 0.0339(13) Uani 1 1 d . . .
H14 H 0.9509 0.4231 0.2946 0.041 Uiso 1 1 calc R . .
C15 C 0.7417(6) 0.5070(4) 0.2882(4) 0.0349(14) Uani 1 1 d . . .
H15 H 0.7431 0.5739 0.3025 0.042 Uiso 1 1 calc R . .
C16 C 1.0099(6) 0.2293(4) 0.2350(4) 0.0327(13) Uani 1 1 d . . .
C17 C 0.7350(6) 0.1953(4) 0.2371(4) 0.0338(13) Uani 1 1 d . . .
C18 C 0.8999(6) 0.6017(4) -0.0922(4) 0.0362(14) Uani 1 1 d . . .
H18 H 0.9879 0.6069 -0.0944 0.043 Uiso 1 1 calc R . .
C19 C 0.8959(7) 0.5004(5) -0.0935(5) 0.0431(15) Uani 1 1 d . . .
H19 H 0.9791 0.4395 -0.0969 0.052 Uiso 1 1 calc R . .
C20 C 0.7656(7) 0.4895(4) -0.0898(4) 0.0411(15) Uani 1 1 d . . .
C21 C 0.6463(6) 0.5841(5) -0.0828(5) 0.0470(17) Uani 1 1 d . . .
H21 H 0.5571 0.5814 -0.0775 0.056 Uiso 1 1 calc R . .
C22 C 0.6623(6) 0.6828(5) -0.0839(5) 0.0417(15) Uani 1 1 d . . .
H22 H 0.5813 0.7454 -0.0817 0.050 Uiso 1 1 calc R . .
C23 C 0.7537(8) 0.3800(5) -0.0956(5) 0.0541(19) Uani 1 1 d . . .
H23A H 0.6552 0.3900 -0.0881 0.065 Uiso 1 1 calc R . .
H23B H 0.7874 0.3501 -0.1550 0.065 Uiso 1 1 calc R . .
C24 C 0.8354(7) 0.3002(4) -0.0267(4) 0.0416(15) Uani 1 1 d . . .
H24A H 0.7974 0.3268 0.0329 0.050 Uiso 1 1 calc R . .
H24B H 0.9331 0.2929 -0.0314 0.050 Uiso 1 1 calc R . .
C25 C 0.8272(6) 0.1904(4) -0.0404(4) 0.0355(13) Uani 1 1 d . . .
C26 C 0.9277(6) 0.1101(4) -0.0930(4) 0.0416(15) Uani 1 1 d . . .
H26 H 1.0028 0.1224 -0.1218 0.050 Uiso 1 1 calc R . .
C27 C 0.9142(6) 0.0120(4) -0.1018(4) 0.0360(14) Uani 1 1 d . . .
H27 H 0.9829 -0.0409 -0.1366 0.043 Uiso 1 1 calc R . .
C28 C 0.7099(6) 0.0666(4) -0.0139(4) 0.0393(15) Uani 1 1 d . . .
H28 H 0.6345 0.0529 0.0128 0.047 Uiso 1 1 calc R . .
C29 C 0.7168(7) 0.1667(4) -0.0016(5) 0.0460(17) Uani 1 1 d . . .
H29 H 0.6465 0.2187 0.0331 0.055 Uiso 1 1 calc R . .
C30 C 0.8588(7) 0.2365(5) 0.5050(5) 0.0521(18) Uani 1 1 d . . .
H30 H 0.9482 0.2329 0.5176 0.063 Uiso 1 1 calc R . .
C31 C 0.7485(7) 0.3371(5) 0.5051(4) 0.0455(16) Uani 1 1 d . . .
H31 H 0.7651 0.3993 0.5164 0.055 Uiso 1 1 calc R . .
C32 C 0.6145(6) 0.3442(5) 0.4884(4) 0.0382(14) Uani 1 1 d . . .
C33 C 0.5978(7) 0.2497(5) 0.4689(5) 0.0493(17) Uani 1 1 d . . .
H33 H 0.5095 0.2509 0.4562 0.059 Uiso 1 1 calc R . .
C34 C 0.7119(8) 0.1536(5) 0.4684(5) 0.0547(19) Uani 1 1 d . . .
H34 H 0.6982 0.0911 0.4537 0.066 Uiso 1 1 calc R . .
C35 C 0.4860(6) 0.4494(4) 0.4893(4) 0.0417(15) Uani 1 1 d . . .
H35A H 0.4165 0.4433 0.5333 0.050 Uiso 1 1 calc R . .
H35B H 0.4454 0.4587 0.4311 0.050 Uiso 1 1 calc R . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Cu1 O6 1.962(4) 2_765 ?
Cu1 O1 1.970(4) . ?
Cu1 N2 2.009(4) 1_565 ?
Cu1 N1 2.053(4) . ?
Cu1 O4 2.291(4) 2_675 ?
Cu2 N3 2.017(5) 2_756 ?
Cu2 N3 2.017(5) . ?
Cu2 O11 2.093(6) 2_756 ?
Cu2 O11 2.093(6) . ?
Cu2 O10 2.259(7) 2_756 ?
Cu2 O10 2.259(7) . ?
O1 C1 1.266(7) . ?
O2 C1 1.244(7) . ?
O3 C2 1.281(7) . ?
O4 C2 1.219(6) . ?
O4 Cu1 2.291(4) 2_675 ?
O5 C3 1.220(6) . ?
O6 C16 1.260(7) . ?
O6 Cu1 1.962(4) 2_765 ?
O7 C16 1.242(7) . ?
O8 C17 1.226(7) . ?
O9 C17 1.289(7) . ?
O9 H9D 0.8200 . ?
O10 H1W 0.8593 . ?
O10 H2W 0.8601 . ?
O11 H3W 0.8593 . ?
O11 H4W 0.8588 . ?
O12 H5W 0.8601 . ?
O12 H6W 0.8600 . ?
O13 H7W 0.8596 . ?
O13 H8W 0.8600 . ?
O14 H9W 0.8604 . ?
O14 H10W 0.8602 . ?
O15 H11W 0.8602 . ?
O15 H12W 0.8602 . ?
N1 C18 1.331(7) . ?
N1 C22 1.334(7) . ?
N2 C27 1.337(7) . ?
N2 C28 1.351(7) . ?
N2 Cu1 2.009(4) 1_545 ?
N3 C34 1.330(9) . ?
N3 C30 1.343(9) . ?
C1 C4 1.514(7) . ?
C2 C5 1.512(7) . ?
C3 C8 1.487(7) . ?
C3 C10 1.499(7) . ?
C4 C9 1.386(7) . ?
C4 C5 1.402(7) . ?
C5 C6 1.384(8) . ?
C6 C7 1.398(7) . ?
C6 H6 0.9300 . ?
C7 C8 1.390(7) . ?
C7 H7 0.9300 . ?
C8 C9 1.390(8) . ?
C9 H9 0.9300 . ?
C10 C15 1.380(8) . ?
C10 C11 1.389(7) . ?
C11 C12 1.402(7) . ?
C11 H11A 0.9300 . ?
C12 C13 1.403(7) . ?
C12 C17 1.490(7) . ?
C13 C14 1.374(7) . ?
C13 C16 1.525(7) . ?
C14 C15 1.390(8) . ?
C14 H14 0.9300 . ?
C15 H15 0.9300 . ?
C18 C19 1.372(8) . ?
C18 H18 0.9300 . ?
C19 C20 1.398(8) . ?
C19 H19 0.9300 . ?
C20 C21 1.389(8) . ?
C20 C23 1.519(8) . ?
C21 C22 1.390(8) . ?
C21 H21 0.9300 . ?
C22 H22 0.9300 . ?
C23 C24 1.510(9) . ?
C23 H23A 0.9700 . ?
C23 H23B 0.9700 . ?
C24 C25 1.519(7) . ?
C24 H24A 0.9700 . ?
C24 H24B 0.9700 . ?
C25 C29 1.384(8) . ?
C25 C26 1.394(8) . ?
C26 C27 1.379(7) . ?
C26 H26 0.9300 . ?
C27 H27 0.9300 . ?
C28 C29 1.383(8) . ?
C28 H28 0.9300 . ?
C29 H29 0.9300 . ?
C30 C31 1.393(8) . ?
C30 H30 0.9300 . ?
C31 C32 1.379(9) . ?
C31 H31 0.9300 . ?
C32 C33 1.376(9) . ?
C32 C35 1.521(7) . ?
C33 C34 1.373(8) . ?
C33 H33 0.9300 . ?
C34 H34 0.9300 . ?
C35 C35 1.527(12) 2_666 ?
C35 H35A 0.9700 . ?
C35 H35B 0.9700 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
O6 Cu1 O1 160.47(17) 2_765 . ?
O6 Cu1 N2 92.10(16) 2_765 1_565 ?
O1 Cu1 N2 92.22(16) . 1_565 ?
O6 Cu1 N1 87.12(16) 2_765 . ?
O1 Cu1 N1 87.57(16) . . ?
N2 Cu1 N1 176.98(18) 1_565 . ?
O6 Cu1 O4 110.21(16) 2_765 2_675 ?
O1 Cu1 O4 88.41(17) . 2_675 ?
N2 Cu1 O4 94.51(16) 1_565 2_675 ?
N1 Cu1 O4 88.49(16) . 2_675 ?
N3 Cu2 N3 180.0(3) 2_756 . ?
N3 Cu2 O11 89.6(2) 2_756 2_756 ?
N3 Cu2 O11 90.4(2) . 2_756 ?
N3 Cu2 O11 90.4(2) 2_756 . ?
N3 Cu2 O11 89.6(2) . . ?
O11 Cu2 O11 180.000(1) 2_756 . ?
N3 Cu2 O10 90.3(2) 2_756 2_756 ?
N3 Cu2 O10 89.7(2) . 2_756 ?
O11 Cu2 O10 89.9(3) 2_756 2_756 ?
O11 Cu2 O10 90.1(3) . 2_756 ?
N3 Cu2 O10 89.7(2) 2_756 . ?
N3 Cu2 O10 90.3(2) . . ?
O11 Cu2 O10 90.1(3) 2_756 . ?
O11 Cu2 O10 89.9(3) . . ?
O10 Cu2 O10 180.000(1) 2_756 . ?
C1 O1 Cu1 117.0(3) . . ?
C2 O4 Cu1 143.5(4) . 2_675 ?
C16 O6 Cu1 129.8(4) . 2_765 ?
C17 O9 H9D 109.5 . . ?
Cu2 O10 H1W 131.5 . . ?
Cu2 O10 H2W 115.3 . . ?
H1W O10 H2W 98.9 . . ?
Cu2 O11 H3W 102.4 . . ?
Cu2 O11 H4W 119.4 . . ?
H3W O11 H4W 105.7 . . ?
H5W O12 H6W 117.9 . . ?
H7W O13 H8W 105.7 . . ?
H9W O14 H10W 97.3 . . ?
H11W O15 H12W 112.6 . . ?
C18 N1 C22 116.2(5) . . ?
C18 N1 Cu1 124.1(4) . . ?
C22 N1 Cu1 119.6(4) . . ?
C27 N2 C28 116.7(4) . . ?
C27 N2 Cu1 122.9(4) . 1_545 ?
C28 N2 Cu1 120.3(4) . 1_545 ?
C34 N3 C30 116.7(5) . . ?
C34 N3 Cu2 122.4(4) . . ?
C30 N3 Cu2 120.7(5) . . ?
O2 C1 O1 125.2(5) . . ?
O2 C1 C4 119.2(5) . . ?
O1 C1 C4 115.5(5) . . ?
O4 C2 O3 124.2(5) . . ?
O4 C2 C5 121.7(5) . . ?
O3 C2 C5 113.9(5) . . ?
O5 C3 C8 120.4(5) . . ?
O5 C3 C10 120.2(5) . . ?
C8 C3 C10 119.4(5) . . ?
C9 C4 C5 118.8(5) . . ?
C9 C4 C1 118.1(5) . . ?
C5 C4 C1 123.0(5) . . ?
C6 C5 C4 120.0(5) . . ?
C6 C5 C2 119.2(5) . . ?
C4 C5 C2 120.5(5) . . ?
C5 C6 C7 120.4(5) . . ?
C5 C6 H6 119.8 . . ?
C7 C6 H6 119.8 . . ?
C8 C7 C6 120.0(5) . . ?
C8 C7 H7 120.0 . . ?
C6 C7 H7 120.0 . . ?
C7 C8 C9 119.0(5) . . ?
C7 C8 C3 119.3(5) . . ?
C9 C8 C3 121.6(5) . . ?
C4 C9 C8 121.7(5) . . ?
C4 C9 H9 119.2 . . ?
C8 C9 H9 119.2 . . ?
C15 C10 C11 119.5(5) . . ?
C15 C10 C3 122.3(5) . . ?
C11 C10 C3 118.2(5) . . ?
C10 C11 C12 120.9(5) . . ?
C10 C11 H11A 119.6 . . ?
C12 C11 H11A 119.6 . . ?
C11 C12 C13 118.4(5) . . ?
C11 C12 C17 120.2(5) . . ?
C13 C12 C17 121.2(5) . . ?
C14 C13 C12 120.0(5) . . ?
C14 C13 C16 116.7(5) . . ?
C12 C13 C16 122.8(5) . . ?
C13 C14 C15 120.8(5) . . ?
C13 C14 H14 119.6 . . ?
C15 C14 H14 119.6 . . ?
C10 C15 C14 120.0(5) . . ?
C10 C15 H15 120.0 . . ?
C14 C15 H15 120.0 . . ?
O7 C16 O6 126.7(5) . . ?
O7 C16 C13 120.3(5) . . ?
O6 C16 C13 112.5(5) . . ?
O8 C17 O9 124.9(5) . . ?
O8 C17 C12 119.8(5) . . ?
O9 C17 C12 115.2(5) . . ?
N1 C18 C19 124.5(5) . . ?
N1 C18 H18 117.8 . . ?
C19 C18 H18 117.8 . . ?
C18 C19 C20 119.3(5) . . ?
C18 C19 H19 120.3 . . ?
C20 C19 H19 120.3 . . ?
C21 C20 C19 116.9(5) . . ?
C21 C20 C23 121.1(6) . . ?
C19 C20 C23 122.0(5) . . ?
C20 C21 C22 119.0(6) . . ?
C20 C21 H21 120.5 . . ?
C22 C21 H21 120.5 . . ?
N1 C22 C21 124.0(5) . . ?
N1 C22 H22 118.0 . . ?
C21 C22 H22 118.0 . . ?
C24 C23 C20 113.7(5) . . ?
C24 C23 H23A 108.8 . . ?
C20 C23 H23A 108.8 . . ?
C24 C23 H23B 108.8 . . ?
C20 C23 H23B 108.8 . . ?
H23A C23 H23B 107.7 . . ?
C23 C24 C25 110.9(5) . . ?
C23 C24 H24A 109.5 . . ?
C25 C24 H24A 109.5 . . ?
C23 C24 H24B 109.5 . . ?
C25 C24 H24B 109.5 . . ?
H24A C24 H24B 108.0 . . ?
C29 C25 C26 117.0(5) . . ?
C29 C25 C24 120.8(5) . . ?
C26 C25 C24 122.2(5) . . ?
C27 C26 C25 119.0(5) . . ?
C27 C26 H26 120.5 . . ?
C25 C26 H26 120.5 . . ?
N2 C27 C26 124.3(5) . . ?
N2 C27 H27 117.8 . . ?
C26 C27 H27 117.8 . . ?
N2 C28 C29 122.2(5) . . ?
N2 C28 H28 118.9 . . ?
C29 C28 H28 118.9 . . ?
C28 C29 C25 120.7(5) . . ?
C28 C29 H29 119.7 . . ?
C25 C29 H29 119.7 . . ?
N3 C30 C31 122.5(7) . . ?
N3 C30 H30 118.8 . . ?
C31 C30 H30 118.8 . . ?
C32 C31 C30 119.7(6) . . ?
C32 C31 H31 120.1 . . ?
C30 C31 H31 120.1 . . ?
C33 C32 C31 117.3(6) . . ?
C33 C32 C35 118.7(6) . . ?
C31 C32 C35 124.0(6) . . ?
C34 C33 C32 119.7(7) . . ?
C34 C33 H33 120.1 . . ?
C32 C33 H33 120.1 . . ?
N3 C34 C33 123.9(7) . . ?
N3 C34 H34 118.0 . . ?
C33 C34 H34 118.0 . . ?
C32 C35 C35 115.3(7) . 2_666 ?
C32 C35 H35A 108.4 . . ?
C35 C35 H35A 108.4 2_666 . ?
C32 C35 H35B 108.4 . . ?
C35 C35 H35B 108.4 2_666 . ?
H35A C35 H35B 107.5 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
O6 Cu1 O1 C1 -9.3(7) 2_765 . . . ?
N2 Cu1 O1 C1 -111.9(4) 1_565 . . . ?
N1 Cu1 O1 C1 65.1(4) . . . . ?
O4 Cu1 O1 C1 153.6(4) 2_675 . . . ?
O6 Cu1 N1 C18 33.6(5) 2_765 . . . ?
O1 Cu1 N1 C18 -127.6(5) . . . . ?
N2 Cu1 N1 C18 -42(4) 1_565 . . . ?
O4 Cu1 N1 C18 143.9(5) 2_675 . . . ?
O6 Cu1 N1 C22 -151.5(5) 2_765 . . . ?
O1 Cu1 N1 C22 47.3(5) . . . . ?
N2 Cu1 N1 C22 133(3) 1_565 . . . ?
O4 Cu1 N1 C22 -41.1(5) 2_675 . . . ?
N3 Cu2 N3 C34 24(100) 2_756 . . . ?
O11 Cu2 N3 C34 -38.1(6) 2_756 . . . ?
O11 Cu2 N3 C34 141.9(6) . . . . ?
O10 Cu2 N3 C34 -128.0(6) 2_756 . . . ?
O10 Cu2 N3 C34 52.0(6) . . . . ?
N3 Cu2 N3 C30 -161(100) 2_756 . . . ?
O11 Cu2 N3 C30 136.8(5) 2_756 . . . ?
O11 Cu2 N3 C30 -43.2(5) . . . . ?
O10 Cu2 N3 C30 46.9(5) 2_756 . . . ?
O10 Cu2 N3 C30 -133.1(5) . . . . ?
Cu1 O1 C1 O2 13.1(7) . . . . ?
Cu1 O1 C1 C4 -162.7(3) . . . . ?
Cu1 O4 C2 O3 141.3(5) 2_675 . . . ?
Cu1 O4 C2 C5 -44.0(10) 2_675 . . . ?
O2 C1 C4 C9 -51.8(8) . . . . ?
O1 C1 C4 C9 124.2(6) . . . . ?
O2 C1 C4 C5 131.5(6) . . . . ?
O1 C1 C4 C5 -52.5(7) . . . . ?
C9 C4 C5 C6 -2.9(8) . . . . ?
C1 C4 C5 C6 173.8(5) . . . . ?
C9 C4 C5 C2 170.6(5) . . . . ?
C1 C4 C5 C2 -12.7(8) . . . . ?
O4 C2 C5 C6 -48.7(8) . . . . ?
O3 C2 C5 C6 126.5(6) . . . . ?
O4 C2 C5 C4 137.7(6) . . . . ?
O3 C2 C5 C4 -47.1(7) . . . . ?
C4 C5 C6 C7 2.5(9) . . . . ?
C2 C5 C6 C7 -171.1(5) . . . . ?
C5 C6 C7 C8 1.1(9) . . . . ?
C6 C7 C8 C9 -4.1(9) . . . . ?
C6 C7 C8 C3 176.4(5) . . . . ?
O5 C3 C8 C7 27.0(8) . . . . ?
C10 C3 C8 C7 -154.5(5) . . . . ?
O5 C3 C8 C9 -152.5(6) . . . . ?
C10 C3 C8 C9 26.0(8) . . . . ?
C5 C4 C9 C8 -0.2(9) . . . . ?
C1 C4 C9 C8 -177.0(5) . . . . ?
C7 C8 C9 C4 3.7(9) . . . . ?
C3 C8 C9 C4 -176.8(5) . . . . ?
O5 C3 C10 C15 -151.0(6) . . . . ?
C8 C3 C10 C15 30.6(8) . . . . ?
O5 C3 C10 C11 28.9(8) . . . . ?
C8 C3 C10 C11 -149.6(5) . . . . ?
C15 C10 C11 C12 -5.2(8) . . . . ?
C3 C10 C11 C12 175.0(5) . . . . ?
C10 C11 C12 C13 1.0(8) . . . . ?
C10 C11 C12 C17 176.7(5) . . . . ?
C11 C12 C13 C14 4.4(8) . . . . ?
C17 C12 C13 C14 -171.2(5) . . . . ?
C11 C12 C13 C16 -167.6(5) . . . . ?
C17 C12 C13 C16 16.8(8) . . . . ?
C12 C13 C14 C15 -5.7(8) . . . . ?
C16 C13 C14 C15 166.7(5) . . . . ?
C11 C10 C15 C14 4.0(9) . . . . ?
C3 C10 C15 C14 -176.2(5) . . . . ?
C13 C14 C15 C10 1.5(9) . . . . ?
Cu1 O6 C16 O7 -18.6(8) 2_765 . . . ?
Cu1 O6 C16 C13 153.3(3) 2_765 . . . ?
C14 C13 C16 O7 67.7(7) . . . . ?
C12 C13 C16 O7 -120.0(6) . . . . ?
C14 C13 C16 O6 -104.7(6) . . . . ?
C12 C13 C16 O6 67.6(7) . . . . ?
C11 C12 C17 O8 -164.4(5) . . . . ?
C13 C12 C17 O8 11.2(8) . . . . ?
C11 C12 C17 O9 13.3(8) . . . . ?
C13 C12 C17 O9 -171.2(5) . . . . ?
C22 N1 C18 C19 0.8(9) . . . . ?
Cu1 N1 C18 C19 175.9(5) . . . . ?
N1 C18 C19 C20 -0.4(10) . . . . ?
C18 C19 C20 C21 -1.4(10) . . . . ?
C18 C19 C20 C23 176.9(6) . . . . ?
C19 C20 C21 C22 2.8(10) . . . . ?
C23 C20 C21 C22 -175.6(6) . . . . ?
C18 N1 C22 C21 0.7(10) . . . . ?
Cu1 N1 C22 C21 -174.6(5) . . . . ?
C20 C21 C22 N1 -2.6(11) . . . . ?
C21 C20 C23 C24 -126.6(7) . . . . ?
C19 C20 C23 C24 55.1(9) . . . . ?
C20 C23 C24 C25 -176.1(6) . . . . ?
C23 C24 C25 C29 -86.8(8) . . . . ?
C23 C24 C25 C26 92.1(7) . . . . ?
C29 C25 C26 C27 -1.6(9) . . . . ?
C24 C25 C26 C27 179.4(6) . . . . ?
C28 N2 C27 C26 0.6(9) . . . . ?
Cu1 N2 C27 C26 -179.9(5) 1_545 . . . ?
C25 C26 C27 N2 0.7(10) . . . . ?
C27 N2 C28 C29 -1.0(9) . . . . ?
Cu1 N2 C28 C29 179.5(5) 1_545 . . . ?
N2 C28 C29 C25 0.1(10) . . . . ?
C26 C25 C29 C28 1.2(10) . . . . ?
C24 C25 C29 C28 -179.8(6) . . . . ?
C34 N3 C30 C31 1.1(10) . . . . ?
Cu2 N3 C30 C31 -174.0(5) . . . . ?
N3 C30 C31 C32 1.3(10) . . . . ?
C30 C31 C32 C33 -2.3(9) . . . . ?
C30 C31 C32 C35 178.3(6) . . . . ?
C31 C32 C33 C34 1.1(10) . . . . ?
C35 C32 C33 C34 -179.5(6) . . . . ?
C30 N3 C34 C33 -2.5(11) . . . . ?
Cu2 N3 C34 C33 172.6(6) . . . . ?
C32 C33 C34 N3 1.4(11) . . . . ?
C33 C32 C35 C35 -179.5(7) . . . 2_666 ?
C31 C32 C35 C35 0.0(10) . . . 2_666 ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
O10 H2W O8 0.86 1.87 2.725(7) 176.3 .
O11 H4W O7 0.86 1.84 2.680(7) 166.9 .
O12 H5W O11 0.86 2.49 2.662(15) 92.2 1_455
O12 H5W O12 0.86 2.61 2.91(3) 101.5 2_656
O13 H7W O9 0.86 2.25 3.079(8) 162.2 .
O13 H8W O14 0.86 2.50 3.181(15) 136.6 .
O14 H9W O13 0.86 2.41 3.181(15) 149.4 .
O14 H10W O5 0.86 1.98 2.845(8) 179.0 .
O15 H11W O2 0.86 1.93 2.788(11) 177.4 .
O15 H12W O10 0.86 2.56 3.42(2) 178.9 1_565

_diffrn_measured_fraction_theta_max 0.993
_diffrn_reflns_theta_full        25.50
_diffrn_measured_fraction_theta_full 0.993
_refine_diff_density_max         1.375
_refine_diff_density_min         -0.487
_refine_diff_density_rms         0.113

data_a
_database_code_depnum_ccdc_archive 'CCDC 656398'

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C82 H90 Cu4 N8 O33'
_chemical_formula_weight         1969.78

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

_symmetry_cell_setting           Monoclinic
_symmetry_space_group_name_H-M   C2/c

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

_cell_length_a                   34.849(5)
_cell_length_b                   13.4109(15)
_cell_length_c                   26.387(3)
_cell_angle_alpha                90.00
_cell_angle_beta                 131.039(4)
_cell_angle_gamma                90.00
_cell_volume                     9301.7(19)
_cell_formula_units_Z            4
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    1122
_cell_measurement_theta_min      2.23
_cell_measurement_theta_max      16.76

_exptl_crystal_description       ?
_exptl_crystal_colour            ?
_exptl_crystal_size_max          0.35
_exptl_crystal_size_mid          0.23
_exptl_crystal_size_min          0.21
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.407
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             4072
_exptl_absorpt_coefficient_mu    0.987
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.7239
_exptl_absorpt_correction_T_max  0.8196
_exptl_absorpt_process_details   sadabs

_exptl_special_details           
;
?
;

_diffrn_ambient_temperature      293(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            21910
_diffrn_reflns_av_R_equivalents  0.1239
_diffrn_reflns_av_sigmaI/netI    0.5479
_diffrn_reflns_limit_h_min       -34
_diffrn_reflns_limit_h_max       42
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_l_min       -31
_diffrn_reflns_limit_l_max       30
_diffrn_reflns_theta_min         1.55
_diffrn_reflns_theta_max         25.50
_reflns_number_total             8406
_reflns_number_gt                1882
_reflns_threshold_expression     >2sigma(I)

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

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

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0607P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         8406
_refine_ls_number_parameters     573
_refine_ls_number_restraints     319
_refine_ls_R_factor_all          0.2289
_refine_ls_R_factor_gt           0.0827
_refine_ls_wR_factor_ref         0.2270
_refine_ls_wR_factor_gt          0.2106
_refine_ls_goodness_of_fit_ref   0.869
_refine_ls_restrained_S_all      0.901
_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 0.75810(5) 0.50148(11) 0.85866(6) 0.0420(4) Uani 1 1 d . . .
Cu2 Cu 0.58261(5) 0.74618(11) 0.62706(7) 0.0482(5) Uani 1 1 d U . .
O1 O 0.6019(4) 0.5732(7) 0.6455(5) 0.103(3) Uani 1 1 d DU . .
O2 O 0.5738(4) 0.6439(8) 0.6883(6) 0.124(4) Uani 1 1 d DU . .
O3 O 0.6833(2) 0.5171(6) 0.7938(3) 0.042(2) Uani 1 1 d U . .
O4 O 0.7013(3) 0.3575(6) 0.8042(4) 0.057(3) Uani 1 1 d U . .
O5 O 0.5659(3) 0.1300(7) 0.7587(4) 0.087(3) Uani 1 1 d U . .
O6 O 0.4131(3) 0.2037(6) 0.4385(4) 0.050(3) Uani 1 1 d U . .
O7 O 0.4212(3) 0.0399(7) 0.4290(4) 0.072(3) Uani 1 1 d U . .
O8 O 0.3286(3) 0.0410(6) 0.4223(4) 0.049(2) Uani 1 1 d U . .
O9 O 0.3464(3) -0.1029(7) 0.4746(4) 0.074(3) Uani 1 1 d U . .
O10 O 0.5638(3) 0.8823(6) 0.6556(4) 0.081(3) Uani 1 1 d U . .
H1W H 0.5750 0.8950 0.6948 0.121 Uiso 1 1 d R . .
H2W H 0.5685 0.9065 0.6304 0.121 Uiso 1 1 d R . .
O11 O 0.6043(5) 1.7348(10) 0.9337(6) 0.183(6) Uani 1 1 d U . .
H3W H 0.6189 1.7831 0.9612 0.275 Uiso 1 1 d R . .
H4W H 0.6053 1.6725 0.9404 0.275 Uiso 1 1 d R . .
O12 O 0.6068(6) 1.5385(11) 0.9569(8) 0.221(6) Uani 1 1 d U . .
H5W H 0.5946 1.5258 0.9173 0.332 Uiso 1 1 d R . .
H6W H 0.6104 1.4830 0.9752 0.332 Uiso 1 1 d R . .
O13 O 0.6213(6) 1.3411(12) 1.0135(8) 0.259(8) Uani 1 1 d U . .
H7W H 0.6203 1.3137 0.9844 0.389 Uiso 1 1 d R . .
H8W H 0.6206 1.2982 1.0359 0.389 Uiso 1 1 d R . .
O14 O 0.5814(7) 1.4762(13) 0.8372(8) 0.267(7) Uani 1 1 d U . .
H9W H 0.5968 1.5118 0.8283 0.401 Uiso 1 1 d R . .
H10W H 0.5500 1.4867 0.8045 0.401 Uiso 1 1 d R . .
O15 O 0.6013(5) 0.9288(10) 0.7835(6) 0.180(5) Uani 1 1 d U . .
H14W H 0.6065 1.3367 0.8777 0.271 Uiso 1 1 d R . .
H13W H 0.6014 1.2327 0.8553 0.271 Uiso 1 1 d R . .
O16 O 0.6168(6) 1.2701(11) 0.8910(8) 0.216(7) Uani 1 1 d U . .
H11W H 0.5932 0.9876 0.7785 0.324 Uiso 1 1 d R . .
H12W H 0.6014 0.8556 0.7776 0.324 Uiso 1 1 d R . .
O17 O 0.5000 0.715(9) 0.7500 1.52(14) Uani 1 2 d SU . .
H16W H 0.5193 0.6973 0.7911 2.287 Uiso 1 1 d R . .
N1 N 0.6579(3) 0.7694(7) 0.7069(4) 0.045(3) Uani 1 1 d . . .
N2 N 1.0087(3) 0.7761(8) 1.0477(5) 0.048(3) Uani 1 1 d . . .
N3 N 0.7642(3) 0.5371(6) 0.7903(4) 0.040(3) Uani 1 1 d . . .
N4 N 0.7538(4) 0.5116(9) 0.4300(4) 0.057(3) Uani 1 1 d U . .
C1 C 0.5764(4) 0.4717(9) 0.6912(6) 0.062(5) Uani 1 1 d D . .
C2 C 0.6137(5) 0.4070(10) 0.7333(6) 0.053(4) Uani 1 1 d . . .
C3 C 0.6012(4) 0.3054(11) 0.7379(5) 0.054(4) Uani 1 1 d . . .
H3 H 0.6270 0.2600 0.7670 0.065 Uiso 1 1 calc R . .
C4 C 0.5496(4) 0.2761(9) 0.6980(5) 0.049(4) Uani 1 1 d . . .
C5 C 0.5134(4) 0.3491(12) 0.6570(6) 0.076(5) Uani 1 1 d . . .
H5 H 0.4791 0.3347 0.6317 0.092 Uiso 1 1 calc R . .
C6 C 0.5279(5) 0.4422(11) 0.6537(6) 0.068(5) Uani 1 1 d . . .
H6 H 0.5025 0.4878 0.6236 0.081 Uiso 1 1 calc R . .
C7 C 0.5846(5) 0.5713(10) 0.6733(7) 0.078(4) Uani 1 1 d DU . .
C8 C 0.6703(4) 0.4263(11) 0.7810(5) 0.047(4) Uani 1 1 d . . .
C9 C 0.5386(5) 0.1734(11) 0.7032(6) 0.069(5) Uani 1 1 d . . .
C10 C 0.4940(4) 0.1195(9) 0.6452(5) 0.050(4) Uani 1 1 d . . .
C11 C 0.4772(4) 0.1388(9) 0.5814(6) 0.063(4) Uani 1 1 d . . .
H11 H 0.4940 0.1857 0.5759 0.076 Uiso 1 1 calc R . .
C12 C 0.4340(5) 0.0860(10) 0.5242(5) 0.059(4) Uani 1 1 d . . .
C13 C 0.4072(4) 0.0237(8) 0.5316(5) 0.043(3) Uani 1 1 d . . .
C14 C 0.4260(4) -0.0001(10) 0.5961(5) 0.070(4) Uani 1 1 d . . .
H14 H 0.4098 -0.0481 0.6017 0.084 Uiso 1 1 calc R . .
C15 C 0.4683(5) 0.0475(10) 0.6506(6) 0.066(4) Uani 1 1 d . . .
H15 H 0.4803 0.0310 0.6931 0.080 Uiso 1 1 calc R . .
C16 C 0.4207(4) 0.1190(15) 0.4567(6) 0.067(5) Uani 1 1 d . . .
C17 C 0.3576(5) -0.0174(11) 0.4728(7) 0.056(4) Uani 1 1 d . . .
C18 C 0.6754(4) 0.7583(8) 0.7680(5) 0.055(4) Uani 1 1 d . . .
H18 H 0.6531 0.7417 0.7746 0.066 Uiso 1 1 calc R . .
C19 C 0.7268(4) 0.7708(8) 0.8234(5) 0.045(3) Uani 1 1 d . . .
H19 H 0.7387 0.7645 0.8667 0.054 Uiso 1 1 calc R . .
C20 C 0.7593(4) 0.7923(8) 0.8134(6) 0.040(4) Uani 1 1 d . . .
C21 C 0.7414(4) 0.8013(8) 0.7524(5) 0.043(3) Uani 1 1 d . . .
H21 H 0.7633 0.8129 0.7443 0.052 Uiso 1 1 calc R . .
C22 C 0.6915(5) 0.7938(8) 0.7013(6) 0.051(4) Uani 1 1 d . . .
H22 H 0.6795 0.8069 0.6584 0.061 Uiso 1 1 calc R . .
C23 C 0.8171(4) 0.8009(9) 0.8784(5) 0.063(4) Uani 1 1 d . . .
H23A H 0.8218 0.8582 0.9043 0.076 Uiso 1 1 calc R . .
H23B H 0.8271 0.7419 0.9058 0.076 Uiso 1 1 calc R . .
C24 C 0.8524(4) 0.8121(10) 0.8614(6) 0.072(5) Uani 1 1 d . . .
H24A H 0.8439 0.7624 0.8287 0.086 Uiso 1 1 calc R . .
H24B H 0.8485 0.8777 0.8430 0.086 Uiso 1 1 calc R . .
C25 C 0.9079(4) 0.7970(11) 0.9282(6) 0.055(4) Uani 1 1 d . . .
C26 C 0.9398(5) 0.8805(10) 0.9615(6) 0.065(4) Uani 1 1 d . . .
H26 H 0.9281 0.9451 0.9459 0.078 Uiso 1 1 calc R . .
C27 C 0.9899(4) 0.8613(11) 1.0192(6) 0.071(5) Uani 1 1 d . . .
H27 H 1.0119 0.9156 1.0392 0.085 Uiso 1 1 calc R . .
C28 C 0.9760(5) 0.7011(10) 1.0146(6) 0.065(4) Uani 1 1 d . . .
H28 H 0.9877 0.6383 1.0340 0.078 Uiso 1 1 calc R . .
C29 C 0.9278(4) 0.7067(9) 0.9557(6) 0.073(5) Uani 1 1 d . . .
H29 H 0.9085 0.6492 0.9345 0.087 Uiso 1 1 calc R . .
C30 C 0.8072(5) 0.5397(8) 0.8035(6) 0.048(3) Uani 1 1 d U . .
H30 H 0.8366 0.5276 0.8476 0.058 Uiso 1 1 calc R . .
C31 C 0.8126(5) 0.5587(9) 0.7579(6) 0.059(4) Uani 1 1 d U . .
H31 H 0.8445 0.5632 0.7705 0.071 Uiso 1 1 calc R . .
C32 C 0.7682(5) 0.5709(9) 0.6916(6) 0.062(3) Uani 1 1 d U . .
C33 C 0.7240(5) 0.5720(9) 0.6769(6) 0.053(3) Uani 1 1 d U . .
H33 H 0.6941 0.5847 0.6333 0.063 Uiso 1 1 calc R . .
C34 C 0.7228(4) 0.5550(8) 0.7251(5) 0.049(3) Uani 1 1 d U . .
H34 H 0.6912 0.5552 0.7135 0.059 Uiso 1 1 calc R . .
C35 C 0.7728(5) 0.5883(11) 0.6390(7) 0.089(4) Uani 1 1 d U . .
H35A H 0.7574 0.6517 0.6170 0.107 Uiso 1 1 calc R . .
H35B H 0.8085 0.5909 0.6606 0.107 Uiso 1 1 calc R . .
C36 C 0.7477(6) 0.5082(13) 0.5890(8) 0.126(5) Uani 1 1 d U . .
H36A H 0.7124 0.5050 0.5688 0.152 Uiso 1 1 calc R . .
H36B H 0.7635 0.4453 0.6117 0.152 Uiso 1 1 calc R . .
C37 C 0.7497(7) 0.5205(16) 0.5344(9) 0.115(5) Uani 1 1 d U . .
C38 C 0.7326(6) 0.4436(15) 0.4920(9) 0.126(5) Uani 1 1 d U . .
H38 H 0.7173 0.3906 0.4957 0.151 Uiso 1 1 calc R . .
C39 C 0.7365(6) 0.4383(13) 0.4415(7) 0.102(5) Uani 1 1 d U . .
H39 H 0.7262 0.3804 0.4161 0.123 Uiso 1 1 calc R . .
C40 C 0.7726(6) 0.5905(12) 0.4705(8) 0.103(5) Uani 1 1 d U . .
H40 H 0.7882 0.6416 0.4660 0.123 Uiso 1 1 calc R . .
C41 C 0.7683(7) 0.5968(15) 0.5230(7) 0.134(8) Uani 1 1 d . . .
H41 H 0.7788 0.6546 0.5485 0.161 Uiso 1 1 calc R . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Cu1 O8 1.939(7) 8_556 ?
Cu1 O3 1.977(7) . ?
Cu1 N4 1.992(11) 6_566 ?
Cu1 N3 2.006(10) . ?
Cu1 C8 2.519(12) . ?
Cu2 O6 1.951(9) 5_666 ?
Cu2 N2 2.007(9) 8_465 ?
Cu2 N1 2.039(9) . ?
Cu2 O10 2.231(9) . ?
Cu2 O2 2.288(13) . ?
Cu2 O1 2.376(10) . ?
O1 C7 1.217(9) . ?
O2 C7 1.200(9) . ?
O3 C8 1.266(13) . ?
O4 C8 1.234(13) . ?
O5 C9 1.248(12) . ?
O6 C16 1.193(17) . ?
O6 Cu2 1.951(9) 5_666 ?
O7 C16 1.296(16) . ?
O8 C17 1.281(13) . ?
O8 Cu1 1.939(7) 8_455 ?
O9 C17 1.222(13) . ?
O10 O15 2.774(15) . ?
O10 H1W 0.8490 . ?
O10 H2W 0.8484 . ?
O11 O12 2.690(19) . ?
O11 H3W 0.8495 . ?
O11 H4W 0.8495 . ?
O12 O14 2.79(2) . ?
O12 O13 2.92(2) . ?
O12 H5W 0.8488 . ?
O12 H6W 0.8500 . ?
O13 H7W 0.8297 . ?
O13 H8W 0.8367 . ?
O14 O16 2.98(2) . ?
O14 H9W 0.8583 . ?
O14 H10W 0.8499 . ?
O15 O16 5.22(2) . ?
O15 H11W 0.8189 . ?
O15 H12W 0.9938 . ?
O16 H14W 0.9407 . ?
O16 H13W 0.8741 . ?
O17 H16W 0.8539 . ?
N1 C18 1.304(14) . ?
N1 C22 1.313(14) . ?
N2 C27 1.286(13) . ?
N2 C28 1.327(14) . ?
N2 Cu2 2.007(9) 8_566 ?
N3 C30 1.300(14) . ?
N3 C34 1.355(12) . ?
N4 C39 1.290(17) . ?
N4 C40 1.330(16) . ?
N4 Cu1 1.992(11) 6_565 ?
C1 C2 1.336(14) . ?
C1 C6 1.339(15) . ?
C1 C7 1.505(9) . ?
C2 C3 1.459(15) . ?
C2 C8 1.510(15) . ?
C3 C4 1.417(14) . ?
C3 H3 0.9300 . ?
C4 C5 1.389(15) . ?
C4 C9 1.460(15) . ?
C5 C6 1.372(16) . ?
C5 H5 0.9300 . ?
C6 H6 0.9300 . ?
C9 C10 1.469(15) . ?
C10 C15 1.386(16) . ?
C10 C11 1.398(15) . ?
C11 C12 1.435(14) . ?
C11 H11 0.9300 . ?
C12 C13 1.360(16) . ?
C12 C16 1.581(19) . ?
C13 C14 1.400(15) . ?
C13 C17 1.477(15) . ?
C14 C15 1.366(13) . ?
C14 H14 0.9300 . ?
C15 H15 0.9300 . ?
C18 C19 1.391(13) . ?
C18 H18 0.9300 . ?
C19 C20 1.348(16) . ?
C19 H19 0.9300 . ?
C20 C21 1.296(15) . ?
C20 C23 1.574(14) . ?
C21 C22 1.333(13) . ?
C21 H21 0.9300 . ?
C22 H22 0.9300 . ?
C23 C24 1.569(18) . ?
C23 H23A 0.9700 . ?
C23 H23B 0.9700 . ?
C24 C25 1.553(14) . ?
C24 H24A 0.9700 . ?
C24 H24B 0.9700 . ?
C25 C29 1.346(15) . ?
C25 C26 1.406(15) . ?
C26 C27 1.394(14) . ?
C26 H26 0.9300 . ?
C27 H27 0.9300 . ?
C28 C29 1.348(14) . ?
C28 H28 0.9300 . ?
C29 H29 0.9300 . ?
C30 C31 1.357(16) . ?
C30 H30 0.9300 . ?
C31 C32 1.389(15) . ?
C31 H31 0.9300 . ?
C32 C33 1.319(16) . ?
C32 C35 1.517(18) . ?
C33 C34 1.318(15) . ?
C33 H33 0.9300 . ?
C34 H34 0.9300 . ?
C35 C36 1.463(17) . ?
C35 H35A 0.9700 . ?
C35 H35B 0.9700 . ?
C36 C37 1.50(2) . ?
C36 H36A 0.9700 . ?
C36 H36B 0.9700 . ?
C37 C38 1.34(2) . ?
C37 C41 1.35(2) . ?
C38 C39 1.43(2) . ?
C38 H38 0.9300 . ?
C39 H39 0.9300 . ?
C40 C41 1.49(2) . ?
C40 H40 0.9300 . ?
C41 H41 0.9300 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
O8 Cu1 O3 168.8(3) 8_556 . ?
O8 Cu1 N4 89.7(4) 8_556 6_566 ?
O3 Cu1 N4 87.4(4) . 6_566 ?
O8 Cu1 N3 91.5(4) 8_556 . ?
O3 Cu1 N3 93.1(3) . . ?
N4 Cu1 N3 171.2(4) 6_566 . ?
O8 Cu1 C8 139.3(4) 8_556 . ?
O3 Cu1 C8 29.7(3) . . ?
N4 Cu1 C8 85.9(4) 6_566 . ?
N3 Cu1 C8 98.8(4) . . ?
O6 Cu2 N2 85.4(4) 5_666 8_465 ?
O6 Cu2 N1 93.9(4) 5_666 . ?
N2 Cu2 N1 179.2(5) 8_465 . ?
O6 Cu2 O10 103.2(3) 5_666 . ?
N2 Cu2 O10 90.8(4) 8_465 . ?
N1 Cu2 O10 89.4(3) . . ?
O6 Cu2 O2 163.0(4) 5_666 . ?
N2 Cu2 O2 88.4(4) 8_465 . ?
N1 Cu2 O2 92.3(4) . . ?
O10 Cu2 O2 92.7(4) . . ?
O6 Cu2 O1 110.0(4) 5_666 . ?
N2 Cu2 O1 93.7(4) 8_465 . ?
N1 Cu2 O1 86.5(3) . . ?
O10 Cu2 O1 146.7(4) . . ?
O2 Cu2 O1 54.6(4) . . ?
C7 O1 Cu2 87.6(9) . . ?
C7 O2 Cu2 92.2(11) . . ?
C8 O3 Cu1 99.6(7) . . ?
C16 O6 Cu2 123.9(10) . 5_666 ?
C17 O8 Cu1 114.0(8) . 8_455 ?
Cu2 O10 O15 125.9(4) . . ?
Cu2 O10 H1W 125.0 . . ?
O15 O10 H1W 1.6 . . ?
Cu2 O10 H2W 78.3 . . ?
O15 O10 H2W 133.7 . . ?
H1W O10 H2W 135.2 . . ?
O12 O11 H3W 129.9 . . ?
O12 O11 H4W 1.6 . . ?
H3W O11 H4W 130.8 . . ?
O11 O12 O14 95.5(7) . . ?
O11 O12 O13 166.8(8) . . ?
O14 O12 O13 97.3(7) . . ?
O11 O12 H5W 90.1 . . ?
O14 O12 H5W 9.7 . . ?
O13 O12 H5W 103.1 . . ?
O11 O12 H6W 163.1 . . ?
O14 O12 H6W 101.3 . . ?
O13 O12 H6W 4.5 . . ?
H5W O12 H6W 106.8 . . ?
O12 O13 H7W 92.4 . . ?
O12 O13 H8W 155.5 . . ?
H7W O13 H8W 110.2 . . ?
O12 O14 O16 90.8(7) . . ?
O12 O14 H9W 110.6 . . ?
O16 O14 H9W 120.7 . . ?
O12 O14 H10W 109.8 . . ?
O16 O14 H10W 119.5 . . ?
H9W O14 H10W 104.4 . . ?
O10 O15 O16 131.0(5) . . ?
O10 O15 H11W 100.5 . . ?
O16 O15 H11W 31.3 . . ?
O10 O15 H12W 68.6 . . ?
O16 O15 H12W 160.1 . . ?
H11W O15 H12W 164.1 . . ?
O14 O16 O15 133.7(6) . . ?
O14 O16 H14W 5.1 . . ?
O15 O16 H14W 138.8 . . ?
O14 O16 H13W 104.4 . . ?
O15 O16 H13W 30.7 . . ?
H14W O16 H13W 109.2 . . ?
C18 N1 C22 116.0(10) . . ?
C18 N1 Cu2 120.0(9) . . ?
C22 N1 Cu2 124.0(9) . . ?
C27 N2 C28 113.6(11) . . ?
C27 N2 Cu2 123.6(9) . 8_566 ?
C28 N2 Cu2 122.2(9) . 8_566 ?
C30 N3 C34 114.4(11) . . ?
C30 N3 Cu1 123.4(8) . . ?
C34 N3 Cu1 122.1(9) . . ?
C39 N4 C40 118.4(14) . . ?
C39 N4 Cu1 119.5(11) . 6_565 ?
C40 N4 Cu1 121.8(11) . 6_565 ?
C2 C1 C6 119.4(12) . . ?
C2 C1 C7 123.7(12) . . ?
C6 C1 C7 116.0(11) . . ?
C1 C2 C3 119.6(11) . . ?
C1 C2 C8 127.5(12) . . ?
C3 C2 C8 112.9(11) . . ?
C4 C3 C2 120.1(11) . . ?
C4 C3 H3 120.0 . . ?
C2 C3 H3 120.0 . . ?
C5 C4 C3 116.3(11) . . ?
C5 C4 C9 125.2(12) . . ?
C3 C4 C9 118.5(11) . . ?
C6 C5 C4 120.4(12) . . ?
C6 C5 H5 119.8 . . ?
C4 C5 H5 119.8 . . ?
C1 C6 C5 124.1(12) . . ?
C1 C6 H6 117.9 . . ?
C5 C6 H6 117.9 . . ?
O2 C7 O1 124.6(15) . . ?
O2 C7 C1 116.9(13) . . ?
O1 C7 C1 118.6(13) . . ?
O4 C8 O3 122.9(11) . . ?
O4 C8 C2 121.5(12) . . ?
O3 C8 C2 115.5(11) . . ?
O4 C8 Cu1 72.3(7) . . ?
O3 C8 Cu1 50.7(5) . . ?
C2 C8 Cu1 166.1(10) . . ?
O5 C9 C4 120.3(11) . . ?
O5 C9 C10 117.6(12) . . ?
C4 C9 C10 122.0(10) . . ?
C15 C10 C11 117.9(10) . . ?
C15 C10 C9 123.2(11) . . ?
C11 C10 C9 118.9(12) . . ?
C10 C11 C12 119.6(12) . . ?
C10 C11 H11 120.2 . . ?
C12 C11 H11 120.2 . . ?
C13 C12 C11 119.9(12) . . ?
C13 C12 C16 127.8(10) . . ?
C11 C12 C16 112.0(12) . . ?
C12 C13 C14 119.8(10) . . ?
C12 C13 C17 121.3(12) . . ?
C14 C13 C17 118.9(12) . . ?
C15 C14 C13 119.6(12) . . ?
C15 C14 H14 120.2 . . ?
C13 C14 H14 120.2 . . ?
C14 C15 C10 122.7(12) . . ?
C14 C15 H15 118.7 . . ?
C10 C15 H15 118.7 . . ?
O6 C16 O7 129.4(15) . . ?
O6 C16 C12 122.9(14) . . ?
O7 C16 C12 107.7(15) . . ?
O9 C17 O8 124.0(12) . . ?
O9 C17 C13 119.5(13) . . ?
O8 C17 C13 116.4(12) . . ?
N1 C18 C19 121.3(13) . . ?
N1 C18 H18 119.3 . . ?
C19 C18 H18 119.3 . . ?
C20 C19 C18 119.1(12) . . ?
C20 C19 H19 120.4 . . ?
C18 C19 H19 120.4 . . ?
C21 C20 C19 118.9(11) . . ?
C21 C20 C23 124.9(13) . . ?
C19 C20 C23 116.3(12) . . ?
C20 C21 C22 119.4(13) . . ?
C20 C21 H21 120.3 . . ?
C22 C21 H21 120.3 . . ?
N1 C22 C21 125.0(12) . . ?
N1 C22 H22 117.5 . . ?
C21 C22 H22 117.5 . . ?
C24 C23 C20 112.4(10) . . ?
C24 C23 H23A 109.1 . . ?
C20 C23 H23A 109.1 . . ?
C24 C23 H23B 109.1 . . ?
C20 C23 H23B 109.1 . . ?
H23A C23 H23B 107.9 . . ?
C25 C24 C23 106.9(11) . . ?
C25 C24 H24A 110.3 . . ?
C23 C24 H24A 110.3 . . ?
C25 C24 H24B 110.3 . . ?
C23 C24 H24B 110.3 . . ?
H24A C24 H24B 108.6 . . ?
C29 C25 C26 117.7(10) . . ?
C29 C25 C24 123.0(12) . . ?
C26 C25 C24 119.3(12) . . ?
C27 C26 C25 116.4(12) . . ?
C27 C26 H26 121.8 . . ?
C25 C26 H26 121.8 . . ?
N2 C27 C26 126.5(12) . . ?
N2 C27 H27 116.8 . . ?
C26 C27 H27 116.8 . . ?
N2 C28 C29 126.7(12) . . ?
N2 C28 H28 116.6 . . ?
C29 C28 H28 116.6 . . ?
C25 C29 C28 118.8(12) . . ?
C25 C29 H29 120.6 . . ?
C28 C29 H29 120.6 . . ?
N3 C30 C31 125.1(12) . . ?
N3 C30 H30 117.5 . . ?
C31 C30 H30 117.5 . . ?
C30 C31 C32 116.8(13) . . ?
C30 C31 H31 121.6 . . ?
C32 C31 H31 121.6 . . ?
C33 C32 C31 119.5(14) . . ?
C33 C32 C35 122.4(12) . . ?
C31 C32 C35 118.1(14) . . ?
C34 C33 C32 119.0(12) . . ?
C34 C33 H33 120.5 . . ?
C32 C33 H33 120.5 . . ?
C33 C34 N3 125.1(12) . . ?
C33 C34 H34 117.5 . . ?
N3 C34 H34 117.5 . . ?
C36 C35 C32 110.6(13) . . ?
C36 C35 H35A 109.5 . . ?
C32 C35 H35A 109.5 . . ?
C36 C35 H35B 109.5 . . ?
C32 C35 H35B 109.5 . . ?
H35A C35 H35B 108.1 . . ?
C35 C36 C37 114.1(16) . . ?
C35 C36 H36A 108.7 . . ?
C37 C36 H36A 108.7 . . ?
C35 C36 H36B 108.7 . . ?
C37 C36 H36B 108.7 . . ?
H36A C36 H36B 107.6 . . ?
C38 C37 C41 114(2) . . ?
C38 C37 C36 116(2) . . ?
C41 C37 C36 129.2(19) . . ?
C37 C38 C39 123.7(19) . . ?
C37 C38 H38 118.1 . . ?
C39 C38 H38 118.1 . . ?
N4 C39 C38 121.9(16) . . ?
N4 C39 H39 119.1 . . ?
C38 C39 H39 119.1 . . ?
N4 C40 C41 119.7(16) . . ?
N4 C40 H40 120.1 . . ?
C41 C40 H40 120.1 . . ?
C37 C41 C40 121.5(17) . . ?
C37 C41 H41 119.3 . . ?
C40 C41 H41 119.3 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
O6 Cu2 O1 C7 -166.3(8) 5_666 . . . ?
N2 Cu2 O1 C7 -79.9(9) 8_465 . . . ?
N1 Cu2 O1 C7 100.9(9) . . . . ?
O10 Cu2 O1 C7 17.3(11) . . . . ?
O2 Cu2 O1 C7 5.5(8) . . . . ?
O6 Cu2 O2 C7 21.6(17) 5_666 . . . ?
N2 Cu2 O2 C7 90.1(9) 8_465 . . . ?
N1 Cu2 O2 C7 -89.6(9) . . . . ?
O10 Cu2 O2 C7 -179.2(9) . . . . ?
O1 Cu2 O2 C7 -5.6(8) . . . . ?
O8 Cu1 O3 C8 -12(2) 8_556 . . . ?
N4 Cu1 O3 C8 -86.4(7) 6_566 . . . ?
N3 Cu1 O3 C8 102.4(7) . . . . ?
O6 Cu2 O10 O15 -141.6(6) 5_666 . . . ?
N2 Cu2 O10 O15 132.9(6) 8_465 . . . ?
N1 Cu2 O10 O15 -47.8(6) . . . . ?
O2 Cu2 O10 O15 44.5(6) . . . . ?
O1 Cu2 O10 O15 34.9(9) . . . . ?
O11 O12 O14 O16 163.9(7) . . . . ?
O13 O12 O14 O16 -12.9(8) . . . . ?
Cu2 O10 O15 O16 158.1(5) . . . . ?
O12 O14 O16 O15 169.5(8) . . . . ?
O10 O15 O16 O14 6.6(14) . . . . ?
O6 Cu2 N1 C18 171.8(9) 5_666 . . . ?
N2 Cu2 N1 C18 174(100) 8_465 . . . ?
O10 Cu2 N1 C18 68.6(9) . . . . ?
O2 Cu2 N1 C18 -24.1(9) . . . . ?
O1 Cu2 N1 C18 -78.4(9) . . . . ?
O6 Cu2 N1 C22 -9.6(10) 5_666 . . . ?
N2 Cu2 N1 C22 -7(35) 8_465 . . . ?
O10 Cu2 N1 C22 -112.8(9) . . . . ?
O2 Cu2 N1 C22 154.6(10) . . . . ?
O1 Cu2 N1 C22 100.3(10) . . . . ?
O8 Cu1 N3 C30 -9.8(9) 8_556 . . . ?
O3 Cu1 N3 C30 -179.6(9) . . . . ?
N4 Cu1 N3 C30 88(3) 6_566 . . . ?
C8 Cu1 N3 C30 -150.3(9) . . . . ?
O8 Cu1 N3 C34 166.2(8) 8_556 . . . ?
O3 Cu1 N3 C34 -3.6(8) . . . . ?
N4 Cu1 N3 C34 -96(3) 6_566 . . . ?
C8 Cu1 N3 C34 25.8(9) . . . . ?
C6 C1 C2 C3 0(2) . . . . ?
C7 C1 C2 C3 -168.5(13) . . . . ?
C6 C1 C2 C8 -178.0(13) . . . . ?
C7 C1 C2 C8 13(2) . . . . ?
C1 C2 C3 C4 -0.3(19) . . . . ?
C8 C2 C3 C4 178.0(11) . . . . ?
C2 C3 C4 C5 -1.4(18) . . . . ?
C2 C3 C4 C9 179.1(12) . . . . ?
C3 C4 C5 C6 4(2) . . . . ?
C9 C4 C5 C6 -177.1(14) . . . . ?
C2 C1 C6 C5 2(2) . . . . ?
C7 C1 C6 C5 171.6(14) . . . . ?
C4 C5 C6 C1 -4(2) . . . . ?
Cu2 O2 C7 O1 10.8(16) . . . . ?
Cu2 O2 C7 C1 -169.7(10) . . . . ?
Cu2 O1 C7 O2 -10.4(16) . . . . ?
Cu2 O1 C7 C1 170.1(11) . . . . ?
C2 C1 C7 O2 -117.9(16) . . . . ?
C6 C1 C7 O2 73.2(18) . . . . ?
C2 C1 C7 O1 62(2) . . . . ?
C6 C1 C7 O1 -107.3(16) . . . . ?
Cu1 O3 C8 O4 -3.9(13) . . . . ?
Cu1 O3 C8 C2 177.9(9) . . . . ?
C1 C2 C8 O4 -160.4(14) . . . . ?
C3 C2 C8 O4 21.5(17) . . . . ?
C1 C2 C8 O3 17.8(19) . . . . ?
C3 C2 C8 O3 -160.3(11) . . . . ?
C1 C2 C8 Cu1 25(4) . . . . ?
C3 C2 C8 Cu1 -154(3) . . . . ?
O8 Cu1 C8 O4 -6.9(10) 8_556 . . . ?
O3 Cu1 C8 O4 176.5(12) . . . . ?
N4 Cu1 C8 O4 -91.7(7) 6_566 . . . ?
N3 Cu1 C8 O4 95.9(7) . . . . ?
O8 Cu1 C8 O3 176.5(6) 8_556 . . . ?
N4 Cu1 C8 O3 91.8(7) 6_566 . . . ?
N3 Cu1 C8 O3 -80.7(7) . . . . ?
O8 Cu1 C8 C2 169(3) 8_556 . . . ?
O3 Cu1 C8 C2 -8(3) . . . . ?
N4 Cu1 C8 C2 84(4) 6_566 . . . ?
N3 Cu1 C8 C2 -89(4) . . . . ?
C5 C4 C9 O5 -141.7(15) . . . . ?
C3 C4 C9 O5 38(2) . . . . ?
C5 C4 C9 C10 35(2) . . . . ?
C3 C4 C9 C10 -145.7(12) . . . . ?
O5 C9 C10 C15 28(2) . . . . ?
C4 C9 C10 C15 -148.4(14) . . . . ?
O5 C9 C10 C11 -149.6(14) . . . . ?
C4 C9 C10 C11 34(2) . . . . ?
C15 C10 C11 C12 1.3(19) . . . . ?
C9 C10 C11 C12 179.4(12) . . . . ?
C10 C11 C12 C13 5.4(19) . . . . ?
C10 C11 C12 C16 179.4(12) . . . . ?
C11 C12 C13 C14 -9(2) . . . . ?
C16 C12 C13 C14 177.5(14) . . . . ?
C11 C12 C13 C17 168.8(11) . . . . ?
C16 C12 C13 C17 -4(2) . . . . ?
C12 C13 C14 C15 7(2) . . . . ?
C17 C13 C14 C15 -171.3(12) . . . . ?
C13 C14 C15 C10 0(2) . . . . ?
C11 C10 C15 C14 -4(2) . . . . ?
C9 C10 C15 C14 178.1(13) . . . . ?
Cu2 O6 C16 O7 -17.9(19) 5_666 . . . ?
Cu2 O6 C16 C12 160.2(9) 5_666 . . . ?
C13 C12 C16 O6 118.6(16) . . . . ?
C11 C12 C16 O6 -54.9(17) . . . . ?
C13 C12 C16 O7 -62.9(18) . . . . ?
C11 C12 C16 O7 123.6(12) . . . . ?
Cu1 O8 C17 O9 16.7(17) 8_455 . . . ?
Cu1 O8 C17 C13 -162.9(9) 8_455 . . . ?
C12 C13 C17 O9 143.0(15) . . . . ?
C14 C13 C17 O9 -38.8(19) . . . . ?
C12 C13 C17 O8 -37.4(18) . . . . ?
C14 C13 C17 O8 140.9(13) . . . . ?
C22 N1 C18 C19 -0.6(16) . . . . ?
Cu2 N1 C18 C19 178.1(8) . . . . ?
N1 C18 C19 C20 -1.8(17) . . . . ?
C18 C19 C20 C21 0.5(17) . . . . ?
C18 C19 C20 C23 -177.5(9) . . . . ?
C19 C20 C21 C22 3.1(17) . . . . ?
C23 C20 C21 C22 -179.1(10) . . . . ?
C18 N1 C22 C21 4.6(18) . . . . ?
Cu2 N1 C22 C21 -174.1(8) . . . . ?
C20 C21 C22 N1 -6.0(19) . . . . ?
C21 C20 C23 C24 -5.3(16) . . . . ?
C19 C20 C23 C24 172.5(11) . . . . ?
C20 C23 C24 C25 -168.2(9) . . . . ?
C23 C24 C25 C29 77.2(17) . . . . ?
C23 C24 C25 C26 -103.9(14) . . . . ?
C29 C25 C26 C27 2(2) . . . . ?
C24 C25 C26 C27 -176.7(13) . . . . ?
C28 N2 C27 C26 4(2) . . . . ?
Cu2 N2 C27 C26 175.4(12) 8_566 . . . ?
C25 C26 C27 N2 -6(2) . . . . ?
C27 N2 C28 C29 2(2) . . . . ?
Cu2 N2 C28 C29 -170.0(12) 8_566 . . . ?
C26 C25 C29 C28 3(2) . . . . ?
C24 C25 C29 C28 -178.6(14) . . . . ?
N2 C28 C29 C25 -5(2) . . . . ?
C34 N3 C30 C31 0.3(17) . . . . ?
Cu1 N3 C30 C31 176.6(9) . . . . ?
N3 C30 C31 C32 -3.6(19) . . . . ?
C30 C31 C32 C33 5.6(19) . . . . ?
C30 C31 C32 C35 -177.7(12) . . . . ?
C31 C32 C33 C34 -4(2) . . . . ?
C35 C32 C33 C34 179.1(12) . . . . ?
C32 C33 C34 N3 1(2) . . . . ?
C30 N3 C34 C33 1.2(17) . . . . ?
Cu1 N3 C34 C33 -175.2(10) . . . . ?
C33 C32 C35 C36 -64.8(19) . . . . ?
C31 C32 C35 C36 118.7(15) . . . . ?
C32 C35 C36 C37 179.0(15) . . . . ?
C35 C36 C37 C38 172.4(17) . . . . ?
C35 C36 C37 C41 -5(3) . . . . ?
C41 C37 C38 C39 4(3) . . . . ?
C36 C37 C38 C39 -173.4(17) . . . . ?
C40 N4 C39 C38 6(2) . . . . ?
Cu1 N4 C39 C38 180.0(12) 6_565 . . . ?
C37 C38 C39 N4 -5(3) . . . . ?
C39 N4 C40 C41 -6(2) . . . . ?
Cu1 N4 C40 C41 179.9(11) 6_565 . . . ?
C38 C37 C41 C40 -4(3) . . . . ?
C36 C37 C41 C40 172.7(17) . . . . ?
N4 C40 C41 C37 6(3) . . . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
O15 H11W O5 0.82 2.04 2.859(16) 174.5 1_565
O16 H13W O5 0.87 2.40 3.276(18) 175.2 1_565
O16 H14W O14 0.94 2.04 2.98(2) 172.6 .
O13 H8W O6 0.84 2.12 2.904(18) 156.5 2_666
O13 H7W O16 0.83 2.46 3.27(3) 167.5 .
O12 H6W O13 0.85 2.07 2.92(2) 173.7 .
O12 H5W O14 0.85 1.96 2.79(2) 166.1 .
O11 H4W O12 0.85 1.84 2.690(19) 177.6 .
O11 H3W O9 0.85 2.00 2.845(16) 179.3 2_676
O10 H2W O7 0.85 1.96 2.806(13) 179.0 5_666
O10 H1W O15 0.85 1.93 2.774(15) 177.7 .

_diffrn_measured_fraction_theta_max 0.970
_diffrn_reflns_theta_full        25.50
_diffrn_measured_fraction_theta_full 0.970
_refine_diff_density_max         0.996
_refine_diff_density_min         -0.554
_refine_diff_density_rms         0.113


# Attachment 'compound_4.cif'

data_4
_database_code_depnum_ccdc_archive 'CCDC 656399'

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C14.50 H16 Mn N O8'
_chemical_formula_weight         387.22

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Mn Mn 0.3368 0.7283 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_symmetry_cell_setting           Monoclinic
_symmetry_space_group_name_H-M   P2/c

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

_cell_length_a                   15.9854(15)
_cell_length_b                   6.1864(6)
_cell_length_c                   16.4143(16)
_cell_angle_alpha                90.00
_cell_angle_beta                 102.6420(10)
_cell_angle_gamma                90.00
_cell_volume                     1583.9(3)
_cell_formula_units_Z            4
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    2831
_cell_measurement_theta_min      2.54
_cell_measurement_theta_max      25.10

_exptl_crystal_description       prism
_exptl_crystal_colour            blue
_exptl_crystal_size_max          0.32
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.13
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.624
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             796
_exptl_absorpt_coefficient_mu    0.878
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.7683
_exptl_absorpt_correction_T_max  0.8929
_exptl_absorpt_process_details   'SADABS (Sheldrick, 2004)'

_exptl_special_details           
;
?
;

_diffrn_ambient_temperature      296(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Bruker APEX-II area-detector diffractometer'
_diffrn_measurement_method       'φ and ω scan'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            7645
_diffrn_reflns_av_R_equivalents  0.0383
_diffrn_reflns_av_sigmaI/netI    0.0468
_diffrn_reflns_limit_h_min       -19
_diffrn_reflns_limit_h_max       17
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_theta_min         2.54
_diffrn_reflns_theta_max         25.10
_reflns_number_total             2831
_reflns_number_gt                2158
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'APEX-II (Bruker, 2004)'
_computing_cell_refinement       'SAINT (Bruker, 2004)'
_computing_data_reduction        SAINT
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    'SHELXTL (Bruker, 2004)'
_computing_publication_material  SHELXTL

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

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0474P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         2831
_refine_ls_number_parameters     251
_refine_ls_number_restraints     7
_refine_ls_R_factor_all          0.0562
_refine_ls_R_factor_gt           0.0399
_refine_ls_wR_factor_ref         0.1043
_refine_ls_wR_factor_gt          0.0936
_refine_ls_goodness_of_fit_ref   1.118
_refine_ls_restrained_S_all      1.117
_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
Mn1 Mn 0.62568(2) 0.56225(7) 0.83116(3) 0.02599(17) Uani 1 1 d . . .
N1 N 0.74505(15) 0.3845(4) 0.90496(16) 0.0337(6) Uani 1 1 d . . .
O1 O 0.61339(16) 0.7461(4) 0.94052(16) 0.0436(6) Uani 1 1 d D . .
O2 O 0.54241(14) 0.3086(4) 0.85939(15) 0.0403(6) Uani 1 1 d D . .
O3 O 0.5000 0.7347(5) 0.7500 0.0290(7) Uani 1 2 d SD . .
O4 O 0.70350(11) 0.8097(3) 0.79777(13) 0.0354(5) Uani 1 1 d . . .
O5 O 0.61772(11) 0.9583(3) 0.68633(13) 0.0326(5) Uani 1 1 d . . .
O6 O 0.62578(12) 1.4120(3) 0.71555(13) 0.0324(5) Uani 1 1 d . . .
O7 O 0.64787(14) 1.4506(4) 0.58801(14) 0.0473(6) Uani 1 1 d . . .
O8 O 1.0000 0.7697(5) 0.7500 0.0570(11) Uani 1 2 d S . .
O9 O 0.45154(15) 0.2122(5) 0.47140(15) 0.0438(6) Uani 1 1 d D . .
C1 C 0.76382(16) 1.0678(4) 0.72312(17) 0.0227(6) Uani 1 1 d . . .
C2 C 0.84422(17) 0.9769(5) 0.74403(18) 0.0277(7) Uani 1 1 d . . .
H2A H 0.8506 0.8398 0.7678 0.033 Uiso 1 1 calc R . .
C3 C 0.91653(16) 1.0857(4) 0.73039(18) 0.0255(7) Uani 1 1 d . . .
C4 C 0.90683(18) 1.2893(5) 0.69427(19) 0.0312(7) Uani 1 1 d . . .
H4 H 0.9545 1.3644 0.6855 0.037 Uiso 1 1 calc R . .
C5 C 0.82621(17) 1.3804(5) 0.67141(19) 0.0291(7) Uani 1 1 d . . .
H5 H 0.8198 1.5157 0.6461 0.035 Uiso 1 1 calc R . .
C6 C 0.75457(16) 1.2724(5) 0.68567(17) 0.0246(6) Uani 1 1 d . . .
C7 C 0.66884(17) 1.3856(5) 0.66131(18) 0.0261(7) Uani 1 1 d . . .
C8 C 0.68790(17) 0.9373(5) 0.73648(19) 0.0269(7) Uani 1 1 d . . .
C9 C 1.0000 0.9660(7) 0.7500 0.0341(11) Uani 1 2 d S . .
C10 C 0.82251(19) 0.4588(6) 0.9031(2) 0.0460(9) Uani 1 1 d . . .
H10 H 0.8264 0.5874 0.8748 0.055 Uiso 1 1 calc R . .
C11 C 0.8974(2) 0.3559(6) 0.9407(2) 0.0523(10) Uani 1 1 d . . .
H11 H 0.9499 0.4141 0.9363 0.063 Uiso 1 1 calc R . .
C12 C 0.8952(2) 0.1683(6) 0.9846(2) 0.0449(9) Uani 1 1 d . . .
C13 C 0.8150(2) 0.0906(6) 0.9865(2) 0.0529(10) Uani 1 1 d . . .
H13 H 0.8095 -0.0359 1.0155 0.064 Uiso 1 1 calc R . .
C14 C 0.7430(2) 0.1995(6) 0.9456(2) 0.0466(9) Uani 1 1 d . . .
H14 H 0.6897 0.1402 0.9464 0.056 Uiso 1 1 calc R . .
C15 C 0.9763(2) 0.0525(7) 1.0288(2) 0.0600(11) Uani 1 1 d . . .
H15A H 1.0139 0.1558 1.0633 0.072 Uiso 1 1 calc R . .
H15B H 0.9612 -0.0567 1.0655 0.072 Uiso 1 1 calc R . .
H1B H 0.632(3) 0.682(7) 0.9872(16) 0.098(18) Uiso 1 1 d D . .
H2B H 0.542(3) 0.262(6) 0.9080(12) 0.078(15) Uiso 1 1 d D . .
H1C H 0.5634(13) 0.764(7) 0.950(3) 0.083(15) Uiso 1 1 d D . .
H2C H 0.4908(11) 0.324(8) 0.834(2) 0.099(17) Uiso 1 1 d D . .
H9C H 0.431(2) 0.114(5) 0.436(2) 0.072(14) Uiso 1 1 d D . .
H9B H 0.425(3) 0.320(5) 0.446(3) 0.092(17) Uiso 1 1 d D . .
H3WA H 0.529(2) 0.817(5) 0.725(2) 0.060(12) Uiso 1 1 d D . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Mn1 O6 2.113(2) 1_545 ?
Mn1 O4 2.119(2) . ?
Mn1 O1 2.170(2) . ?
Mn1 O2 2.173(2) . ?
Mn1 N1 2.304(2) . ?
Mn1 O3 2.4037(14) . ?
N1 C10 1.328(4) . ?
N1 C14 1.328(4) . ?
O1 H1B 0.856(10) . ?
O1 H1C 0.851(10) . ?
O2 H2B 0.849(10) . ?
O2 H2C 0.845(10) . ?
O3 Mn1 2.4037(14) 2_656 ?
O3 H3WA 0.853(10) . ?
O4 C8 1.260(3) . ?
O5 C8 1.245(3) . ?
O6 C7 1.249(3) . ?
O6 Mn1 2.113(2) 1_565 ?
O7 C7 1.243(3) . ?
O8 C9 1.215(5) . ?
O9 H9C 0.853(10) . ?
O9 H9B 0.851(10) . ?
C1 C2 1.376(4) . ?
C1 C6 1.401(4) . ?
C1 C8 1.513(4) . ?
C2 C3 1.397(4) . ?
C2 H2A 0.9300 . ?
C3 C4 1.386(4) . ?
C3 C9 1.498(3) . ?
C4 C5 1.381(4) . ?
C4 H4 0.9300 . ?
C5 C6 1.389(4) . ?
C5 H5 0.9300 . ?
C6 C7 1.513(4) . ?
C9 C3 1.498(3) 2_756 ?
C10 C11 1.377(4) . ?
C10 H10 0.9300 . ?
C11 C12 1.371(5) . ?
C11 H11 0.9300 . ?
C12 C13 1.375(5) . ?
C12 C15 1.520(4) . ?
C13 C14 1.376(4) . ?
C13 H13 0.9300 . ?
C14 H14 0.9300 . ?
C15 C15 1.484(7) 3_757 ?
C15 H15A 0.9700 . ?
C15 H15B 0.9700 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
O6 Mn1 O4 88.26(8) 1_545 . ?
O6 Mn1 O1 172.44(9) 1_545 . ?
O4 Mn1 O1 89.99(9) . . ?
O6 Mn1 O2 89.69(9) 1_545 . ?
O4 Mn1 O2 177.31(9) . . ?
O1 Mn1 O2 91.81(9) . . ?
O6 Mn1 N1 95.67(8) 1_545 . ?
O4 Mn1 N1 90.88(8) . . ?
O1 Mn1 N1 91.71(10) . . ?
O2 Mn1 N1 91.07(9) . . ?
O6 Mn1 O3 82.09(7) 1_545 . ?
O4 Mn1 O3 90.16(8) . . ?
O1 Mn1 O3 90.56(8) . . ?
O2 Mn1 O3 87.82(8) . . ?
N1 Mn1 O3 177.50(9) . . ?
C10 N1 C14 115.8(3) . . ?
C10 N1 Mn1 119.5(2) . . ?
C14 N1 Mn1 124.5(2) . . ?
Mn1 O1 H1B 115(3) . . ?
Mn1 O1 H1C 118(3) . . ?
H1B O1 H1C 94(4) . . ?
Mn1 O2 H2B 125(3) . . ?
Mn1 O2 H2C 113(3) . . ?
H2B O2 H2C 107(4) . . ?
Mn1 O3 Mn1 127.31(13) 2_656 . ?
Mn1 O3 H3WA 118(3) 2_656 . ?
Mn1 O3 H3WA 93(2) . . ?
C8 O4 Mn1 129.37(18) . . ?
C7 O6 Mn1 143.71(18) . 1_565 ?
H9C O9 H9B 98(4) . . ?
C2 C1 C6 118.8(2) . . ?
C2 C1 C8 118.8(2) . . ?
C6 C1 C8 122.3(2) . . ?
C1 C2 C3 121.6(3) . . ?
C1 C2 H2A 119.2 . . ?
C3 C2 H2A 119.2 . . ?
C4 C3 C2 119.2(3) . . ?
C4 C3 C9 123.5(3) . . ?
C2 C3 C9 117.2(3) . . ?
C5 C4 C3 119.8(3) . . ?
C5 C4 H4 120.1 . . ?
C3 C4 H4 120.1 . . ?
C4 C5 C6 120.8(3) . . ?
C4 C5 H5 119.6 . . ?
C6 C5 H5 119.6 . . ?
C5 C6 C1 119.8(2) . . ?
C5 C6 C7 117.7(3) . . ?
C1 C6 C7 122.5(2) . . ?
O7 C7 O6 125.0(3) . . ?
O7 C7 C6 116.3(3) . . ?
O6 C7 C6 118.7(3) . . ?
O5 C8 O4 125.8(3) . . ?
O5 C8 C1 119.0(3) . . ?
O4 C8 C1 115.2(2) . . ?
O8 C9 C3 119.62(18) . 2_756 ?
O8 C9 C3 119.62(18) . . ?
C3 C9 C3 120.8(4) 2_756 . ?
N1 C10 C11 123.6(3) . . ?
N1 C10 H10 118.2 . . ?
C11 C10 H10 118.2 . . ?
C12 C11 C10 120.5(3) . . ?
C12 C11 H11 119.8 . . ?
C10 C11 H11 119.8 . . ?
C11 C12 C13 116.1(3) . . ?
C11 C12 C15 122.2(3) . . ?
C13 C12 C15 121.8(3) . . ?
C12 C13 C14 120.1(3) . . ?
C12 C13 H13 119.9 . . ?
C14 C13 H13 119.9 . . ?
N1 C14 C13 123.8(3) . . ?
N1 C14 H14 118.1 . . ?
C13 C14 H14 118.1 . . ?
C15 C15 C12 113.8(4) 3_757 . ?
C15 C15 H15A 108.8 3_757 . ?
C12 C15 H15A 108.8 . . ?
C15 C15 H15B 108.8 3_757 . ?
C12 C15 H15B 108.8 . . ?
H15A C15 H15B 107.7 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
O6 Mn1 N1 C10 83.3(3) 1_545 . . . ?
O4 Mn1 N1 C10 -5.1(3) . . . . ?
O1 Mn1 N1 C10 -95.1(3) . . . . ?
O2 Mn1 N1 C10 173.1(3) . . . . ?
O3 Mn1 N1 C10 109.5(16) . . . . ?
O6 Mn1 N1 C14 -91.5(3) 1_545 . . . ?
O4 Mn1 N1 C14 -179.8(3) . . . . ?
O1 Mn1 N1 C14 90.2(3) . . . . ?
O2 Mn1 N1 C14 -1.7(3) . . . . ?
O3 Mn1 N1 C14 -65.2(17) . . . . ?
O6 Mn1 O3 Mn1 55.64(6) 1_545 . . 2_656 ?
O4 Mn1 O3 Mn1 143.86(6) . . . 2_656 ?
O1 Mn1 O3 Mn1 -126.14(7) . . . 2_656 ?
O2 Mn1 O3 Mn1 -34.36(7) . . . 2_656 ?
N1 Mn1 O3 Mn1 29.3(17) . . . 2_656 ?
O6 Mn1 O4 C8 60.3(3) 1_545 . . . ?
O1 Mn1 O4 C8 -112.4(3) . . . . ?
O2 Mn1 O4 C8 20(2) . . . . ?
N1 Mn1 O4 C8 155.9(3) . . . . ?
O3 Mn1 O4 C8 -21.8(2) . . . . ?
C6 C1 C2 C3 1.4(4) . . . . ?
C8 C1 C2 C3 177.6(3) . . . . ?
C1 C2 C3 C4 -0.6(5) . . . . ?
C1 C2 C3 C9 -175.9(2) . . . . ?
C2 C3 C4 C5 -0.8(5) . . . . ?
C9 C3 C4 C5 174.2(3) . . . . ?
C3 C4 C5 C6 1.3(5) . . . . ?
C4 C5 C6 C1 -0.5(4) . . . . ?
C4 C5 C6 C7 178.2(3) . . . . ?
C2 C1 C6 C5 -0.8(4) . . . . ?
C8 C1 C6 C5 -176.9(3) . . . . ?
C2 C1 C6 C7 -179.4(3) . . . . ?
C8 C1 C6 C7 4.5(4) . . . . ?
Mn1 O6 C7 O7 -115.9(3) 1_565 . . . ?
Mn1 O6 C7 C6 62.2(4) 1_565 . . . ?
C5 C6 C7 O7 54.0(4) . . . . ?
C1 C6 C7 O7 -127.4(3) . . . . ?
C5 C6 C7 O6 -124.2(3) . . . . ?
C1 C6 C7 O6 54.4(4) . . . . ?
Mn1 O4 C8 O5 8.1(4) . . . . ?
Mn1 O4 C8 C1 -169.60(17) . . . . ?
C2 C1 C8 O5 -145.5(3) . . . . ?
C6 C1 C8 O5 30.6(4) . . . . ?
C2 C1 C8 O4 32.3(4) . . . . ?
C6 C1 C8 O4 -151.6(3) . . . . ?
C4 C3 C9 O8 -151.3(2) . . . . ?
C2 C3 C9 O8 23.8(3) . . . . ?
C4 C3 C9 C3 28.7(2) . . . 2_756 ?
C2 C3 C9 C3 -156.2(3) . . . 2_756 ?
C14 N1 C10 C11 -0.5(5) . . . . ?
Mn1 N1 C10 C11 -175.7(3) . . . . ?
N1 C10 C11 C12 -1.4(6) . . . . ?
C10 C11 C12 C13 1.4(6) . . . . ?
C10 C11 C12 C15 -178.5(4) . . . . ?
C11 C12 C13 C14 0.2(6) . . . . ?
C15 C12 C13 C14 -179.8(3) . . . . ?
C10 N1 C14 C13 2.3(5) . . . . ?
Mn1 N1 C14 C13 177.2(3) . . . . ?
C12 C13 C14 N1 -2.2(6) . . . . ?
C11 C12 C15 C15 -70.7(6) . . . 3_757 ?
C13 C12 C15 C15 109.3(5) . . . 3_757 ?

_diffrn_measured_fraction_theta_max 0.998
_diffrn_reflns_theta_full        25.10
_diffrn_measured_fraction_theta_full 0.998
_refine_diff_density_max         0.295
_refine_diff_density_min         -0.408
_refine_diff_density_rms         0.069

# Attachment 'compound_5.cif'

data_5
_database_code_depnum_ccdc_archive 'CCDC 656400'

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C14.50 H15 Co N O8'
_chemical_formula_weight         390.20

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Co Co 0.3494 0.9721 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_symmetry_cell_setting           Monoclinic
_symmetry_space_group_name_H-M   P2/c

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

_cell_length_a                   15.9043(13)
_cell_length_b                   6.1361(5)
_cell_length_c                   16.1034(14)
_cell_angle_alpha                90.00
_cell_angle_beta                 102.5100(10)
_cell_angle_gamma                90.00
_cell_volume                     1534.2(2)
_cell_formula_units_Z            4
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    2730
_cell_measurement_theta_min      1.31
_cell_measurement_theta_max      25.10

_exptl_crystal_description       block
_exptl_crystal_colour            red
_exptl_crystal_size_max          0.22
_exptl_crystal_size_mid          0.14
_exptl_crystal_size_min          0.08
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.689
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             800
_exptl_absorpt_coefficient_mu    1.164
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.7879
_exptl_absorpt_correction_T_max  0.9126
_exptl_absorpt_process_details   'SADABS (Sheldrick, 2004)'

_exptl_special_details           
;
?
;

_diffrn_ambient_temperature      296(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Bruker APEX-II area-detector diffractometer'
_diffrn_measurement_method       'φ and ω scan'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            7404
_diffrn_reflns_av_R_equivalents  0.0410
_diffrn_reflns_av_sigmaI/netI    0.0512
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_h_max       18
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_limit_l_max       9
_diffrn_reflns_theta_min         1.31
_diffrn_reflns_theta_max         25.10
_reflns_number_total             2730
_reflns_number_gt                2088
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'APEX-II (Bruker, 2004)'
_computing_cell_refinement       'SAINT (Bruker, 2004)'
_computing_data_reduction        SAINT
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    'SHELXTL (Bruker, 2004)'
_computing_publication_material  SHELXTL

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

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0397P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         2730
_refine_ls_number_parameters     255
_refine_ls_number_restraints     8
_refine_ls_R_factor_all          0.0546
_refine_ls_R_factor_gt           0.0377
_refine_ls_wR_factor_ref         0.0898
_refine_ls_wR_factor_gt          0.0812
_refine_ls_goodness_of_fit_ref   1.063
_refine_ls_restrained_S_all      1.061
_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
Co1 Co 0.37430(2) 0.94408(6) 0.16933(3) 0.02423(15) Uani 1 1 d . . .
N1 N 0.25973(15) 1.1140(4) 0.09714(17) 0.0294(6) Uani 1 1 d . . .
O1 O 0.38554(18) 0.7613(4) 0.06446(18) 0.0397(6) Uani 1 1 d D . .
O2 O 0.45599(14) 1.1820(4) 0.14261(17) 0.0345(6) Uani 1 1 d D . .
O3 O 0.5000 0.7824(5) 0.2500 0.0267(7) Uani 1 2 d SD . .
O4 O 0.29735(12) 0.7089(3) 0.20218(14) 0.0311(5) Uani 1 1 d . . .
O5 O 0.38405(12) 0.5509(3) 0.31398(14) 0.0306(5) Uani 1 1 d . . .
O6 O 0.37627(12) 0.0944(3) 0.28367(14) 0.0298(5) Uani 1 1 d . . .
O7 O 0.35153(15) 0.0511(4) 0.41202(15) 0.0478(7) Uani 1 1 d . . .
O8 O 0.0000 0.7459(6) 0.2500 0.0909(19) Uani 1 2 d S . .
C1 C 0.1806(2) 1.0440(6) 0.0981(2) 0.0416(9) Uani 1 1 d . . .
H1A H 0.1746 0.9086 0.1220 0.050 Uiso 1 1 calc R . .
C2 C 0.1068(2) 1.1626(7) 0.0651(2) 0.0480(10) Uani 1 1 d . . .
H2 H 0.0531 1.1061 0.0671 0.058 Uiso 1 1 calc R . .
C3 C 0.1132(2) 1.3657(6) 0.0291(2) 0.0423(9) Uani 1 1 d . . .
C4 C 0.1947(2) 1.4339(6) 0.0262(3) 0.0481(10) Uani 1 1 d . . .
H4 H 0.2024 1.5655 0.0001 0.058 Uiso 1 1 calc R . .
C5 C 0.2649(2) 1.3088(6) 0.0615(2) 0.0420(9) Uani 1 1 d . . .
H5 H 0.3194 1.3629 0.0606 0.050 Uiso 1 1 calc R . .
C6 C 0.0396(2) 1.5132(8) -0.0035(3) 0.0543(11) Uani 1 1 d D . .
C7 C 0.31354(18) 0.5756(5) 0.2635(2) 0.0254(7) Uani 1 1 d . . .
C8 C 0.23730(17) 0.4434(5) 0.27666(19) 0.0224(7) Uani 1 1 d . . .
C9 C 0.15619(18) 0.5349(5) 0.2562(2) 0.0318(8) Uani 1 1 d . . .
H9 H 0.1499 0.6736 0.2324 0.038 Uiso 1 1 calc R . .
C10 C 0.08374(18) 0.4277(5) 0.2699(2) 0.0329(8) Uani 1 1 d . . .
C11 C 0.0000 0.5458(8) 0.2500 0.0447(14) Uani 1 2 d S . .
C12 C 0.09355(19) 0.2213(5) 0.3067(2) 0.0363(9) Uani 1 1 d . . .
H12 H 0.0457 0.1465 0.3164 0.044 Uiso 1 1 calc R . .
C13 C 0.17387(19) 0.1282(5) 0.3287(2) 0.0318(8) Uani 1 1 d . . .
H13 H 0.1801 -0.0088 0.3539 0.038 Uiso 1 1 calc R . .
C14 C 0.24599(18) 0.2365(5) 0.3136(2) 0.0236(7) Uani 1 1 d . . .
C15 C 0.33117(19) 0.1206(5) 0.3379(2) 0.0255(7) Uani 1 1 d . . .
O9 O 0.45427(16) 0.7161(5) 0.47285(17) 0.0417(6) Uani 1 1 d D . .
H1B H 0.368(3) 0.817(7) 0.0175(15) 0.085(18) Uiso 1 1 d D . .
H2B H 0.453(2) 1.231(6) 0.0945(11) 0.056(13) Uiso 1 1 d D . .
H9B H 0.434(3) 0.615(5) 0.442(2) 0.088(18) Uiso 1 1 d D . .
H1C H 0.4344(11) 0.745(6) 0.057(2) 0.055(13) Uiso 1 1 d D . .
H2C H 0.5062(10) 1.156(6) 0.165(2) 0.066(14) Uiso 1 1 d D . .
H9C H 0.429(2) 0.828(4) 0.454(2) 0.052(13) Uiso 1 1 d D . .
H6A H 0.040(3) 1.643(4) -0.019(4) 0.14(3) Uiso 1 1 d D . .
H3WA H 0.470(2) 0.705(5) 0.274(2) 0.068(14) Uiso 1 1 d D . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Co1 O4 2.035(2) . ?
Co1 O6 2.054(2) 1_565 ?
Co1 O2 2.061(2) . ?
Co1 O1 2.067(3) . ?
Co1 N1 2.200(2) . ?
Co1 O3 2.3544(13) . ?
N1 C1 1.333(4) . ?
N1 C5 1.336(4) . ?
O1 H1B 0.822(10) . ?
O1 H1C 0.820(10) . ?
O2 H2B 0.823(10) . ?
O2 H2C 0.819(10) . ?
O3 Co1 2.3544(13) 2_655 ?
O3 H3WA 0.825(10) . ?
O4 C7 1.265(4) . ?
O5 C7 1.244(3) . ?
O6 C15 1.255(3) . ?
O6 Co1 2.054(2) 1_545 ?
O7 C15 1.242(4) . ?
O8 C11 1.228(5) . ?
C1 C2 1.385(5) . ?
C1 H1A 0.9300 . ?
C2 C3 1.388(5) . ?
C2 H2 0.9300 . ?
C3 C4 1.373(5) . ?
C3 C6 1.482(5) . ?
C4 C5 1.374(4) . ?
C4 H4 0.9300 . ?
C5 H5 0.9300 . ?
C6 C6 1.299(8) 3_585 ?
C6 H6A 0.837(19) . ?
C7 C8 1.512(4) . ?
C8 C9 1.380(4) . ?
C8 C14 1.396(4) . ?
C9 C10 1.385(4) . ?
C9 H9 0.9300 . ?
C10 C12 1.393(4) . ?
C10 C11 1.489(4) . ?
C11 C10 1.489(4) 2 ?
C12 C13 1.374(4) . ?
C12 H12 0.9300 . ?
C13 C14 1.392(4) . ?
C13 H13 0.9300 . ?
C14 C15 1.505(4) . ?
O9 H9B 0.820(10) . ?
O9 H9C 0.818(10) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
O4 Co1 O6 88.78(8) . 1_565 ?
O4 Co1 O2 176.96(10) . . ?
O6 Co1 O2 88.92(9) 1_565 . ?
O4 Co1 O1 89.48(10) . . ?
O6 Co1 O1 171.51(10) 1_565 . ?
O2 Co1 O1 92.51(10) . . ?
O4 Co1 N1 89.85(9) . . ?
O6 Co1 N1 96.36(9) 1_565 . ?
O2 Co1 N1 92.37(10) . . ?
O1 Co1 N1 91.94(11) . . ?
O4 Co1 O3 92.55(8) . . ?
O6 Co1 O3 81.28(7) 1_565 . ?
O2 Co1 O3 85.14(9) . . ?
O1 Co1 O3 90.50(9) . . ?
N1 Co1 O3 176.59(10) . . ?
C1 N1 C5 116.1(3) . . ?
C1 N1 Co1 121.1(2) . . ?
C5 N1 Co1 122.0(2) . . ?
Co1 O1 H1B 117(3) . . ?
Co1 O1 H1C 116(3) . . ?
H1B O1 H1C 93(4) . . ?
Co1 O2 H2B 123(3) . . ?
Co1 O2 H2C 111(3) . . ?
H2B O2 H2C 110(4) . . ?
Co1 O3 Co1 130.16(13) 2_655 . ?
Co1 O3 H3WA 119(3) 2_655 . ?
Co1 O3 H3WA 90(3) . . ?
C7 O4 Co1 129.00(19) . . ?
C15 O6 Co1 141.41(19) . 1_545 ?
N1 C1 C2 123.4(3) . . ?
N1 C1 H1A 118.3 . . ?
C2 C1 H1A 118.3 . . ?
C1 C2 C3 120.0(3) . . ?
C1 C2 H2 120.0 . . ?
C3 C2 H2 120.0 . . ?
C4 C3 C2 116.3(3) . . ?
C4 C3 C6 118.7(4) . . ?
C2 C3 C6 125.0(3) . . ?
C3 C4 C5 120.3(3) . . ?
C3 C4 H4 119.8 . . ?
C5 C4 H4 119.8 . . ?
N1 C5 C4 123.9(3) . . ?
N1 C5 H5 118.1 . . ?
C4 C5 H5 118.1 . . ?
C6 C6 C3 126.8(6) 3_585 . ?
C6 C6 H6A 103(4) 3_585 . ?
C3 C6 H6A 129(4) . . ?
O5 C7 O4 126.3(3) . . ?
O5 C7 C8 118.7(3) . . ?
O4 C7 C8 115.0(3) . . ?
C9 C8 C14 118.2(3) . . ?
C9 C8 C7 119.0(3) . . ?
C14 C8 C7 122.6(2) . . ?
C8 C9 C10 122.4(3) . . ?
C8 C9 H9 118.8 . . ?
C10 C9 H9 118.8 . . ?
C9 C10 C12 118.6(3) . . ?
C9 C10 C11 118.1(3) . . ?
C12 C10 C11 123.1(3) . . ?
O8 C11 C10 119.1(2) . . ?
O8 C11 C10 119.1(2) . 2 ?
C10 C11 C10 121.8(4) . 2 ?
C13 C12 C10 120.0(3) . . ?
C13 C12 H12 120.0 . . ?
C10 C12 H12 120.0 . . ?
C12 C13 C14 120.8(3) . . ?
C12 C13 H13 119.6 . . ?
C14 C13 H13 119.6 . . ?
C13 C14 C8 119.9(3) . . ?
C13 C14 C15 117.3(3) . . ?
C8 C14 C15 122.8(2) . . ?
O7 C15 O6 123.7(3) . . ?
O7 C15 C14 116.4(3) . . ?
O6 C15 C14 119.8(3) . . ?
H9B O9 H9C 108(4) . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
O4 Co1 N1 C1 4.9(3) . . . . ?
O6 Co1 N1 C1 -83.8(3) 1_565 . . . ?
O2 Co1 N1 C1 -173.0(3) . . . . ?
O1 Co1 N1 C1 94.4(3) . . . . ?
O3 Co1 N1 C1 -129.9(11) . . . . ?
O4 Co1 N1 C5 174.3(3) . . . . ?
O6 Co1 N1 C5 85.5(3) 1_565 . . . ?
O2 Co1 N1 C5 -3.7(3) . . . . ?
O1 Co1 N1 C5 -96.3(3) . . . . ?
O3 Co1 N1 C5 39.4(14) . . . . ?
O4 Co1 O3 Co1 -143.45(6) . . . 2_655 ?
O6 Co1 O3 Co1 -55.08(6) 1_565 . . 2_655 ?
O2 Co1 O3 Co1 34.57(7) . . . 2_655 ?
O1 Co1 O3 Co1 127.05(7) . . . 2_655 ?
N1 Co1 O3 Co1 -8.7(12) . . . 2_655 ?
O6 Co1 O4 C7 -62.7(3) 1_565 . . . ?
O2 Co1 O4 C7 -22.0(19) . . . . ?
O1 Co1 O4 C7 109.0(3) . . . . ?
N1 Co1 O4 C7 -159.1(3) . . . . ?
O3 Co1 O4 C7 18.5(3) . . . . ?
C5 N1 C1 C2 -0.4(6) . . . . ?
Co1 N1 C1 C2 169.5(3) . . . . ?
N1 C1 C2 C3 -0.3(6) . . . . ?
C1 C2 C3 C4 2.0(6) . . . . ?
C1 C2 C3 C6 -176.2(4) . . . . ?
C2 C3 C4 C5 -3.2(6) . . . . ?
C6 C3 C4 C5 175.1(4) . . . . ?
C1 N1 C5 C4 -0.8(6) . . . . ?
Co1 N1 C5 C4 -170.7(3) . . . . ?
C3 C4 C5 N1 2.8(6) . . . . ?
C4 C3 C6 C6 -171.2(6) . . . 3_585 ?
C2 C3 C6 C6 7.0(9) . . . 3_585 ?
Co1 O4 C7 O5 -5.5(5) . . . . ?
Co1 O4 C7 C8 171.74(18) . . . . ?
O5 C7 C8 C9 146.1(3) . . . . ?
O4 C7 C8 C9 -31.4(4) . . . . ?
O5 C7 C8 C14 -29.9(4) . . . . ?
O4 C7 C8 C14 152.6(3) . . . . ?
C14 C8 C9 C10 -1.0(5) . . . . ?
C7 C8 C9 C10 -177.2(3) . . . . ?
C8 C9 C10 C12 0.9(5) . . . . ?
C8 C9 C10 C11 176.7(3) . . . . ?
C9 C10 C11 O8 -24.0(4) . . . . ?
C12 C10 C11 O8 151.6(3) . . . . ?
C9 C10 C11 C10 156.0(4) . . . 2 ?
C12 C10 C11 C10 -28.4(3) . . . 2 ?
C9 C10 C12 C13 0.0(5) . . . . ?
C11 C10 C12 C13 -175.5(3) . . . . ?
C10 C12 C13 C14 -0.9(5) . . . . ?
C12 C13 C14 C8 0.8(5) . . . . ?
C12 C13 C14 C15 -178.7(3) . . . . ?
C9 C8 C14 C13 0.1(5) . . . . ?
C7 C8 C14 C13 176.2(3) . . . . ?
C9 C8 C14 C15 179.6(3) . . . . ?
C7 C8 C14 C15 -4.3(5) . . . . ?
Co1 O6 C15 O7 115.5(3) 1_545 . . . ?
Co1 O6 C15 C14 -62.8(4) 1_545 . . . ?
C13 C14 C15 O7 -52.7(4) . . . . ?
C8 C14 C15 O7 127.8(3) . . . . ?
C13 C14 C15 O6 125.7(3) . . . . ?
C8 C14 C15 O6 -53.8(4) . . . . ?

_diffrn_measured_fraction_theta_max 0.997
_diffrn_reflns_theta_full        25.10
_diffrn_measured_fraction_theta_full 0.997
_refine_diff_density_max         0.322
_refine_diff_density_min         -0.298
_refine_diff_density_rms         0.070

# Attachment 'compound_6.cif'

data_6
_database_code_depnum_ccdc_archive 'CCDC 656401'

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C14.50 H15 Mn N O8'
_chemical_formula_weight         386.21

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Mn Mn 0.3368 0.7283 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_symmetry_cell_setting           Monoclinic
_symmetry_space_group_name_H-M   P2/c

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

_cell_length_a                   16.0396(16)
_cell_length_b                   6.2190(6)
_cell_length_c                   16.2606(17)
_cell_angle_alpha                90.00
_cell_angle_beta                 102.7870(10)
_cell_angle_gamma                90.00
_cell_volume                     1581.8(3)
_cell_formula_units_Z            4
_cell_measurement_temperature    291(2)
_cell_measurement_reflns_used    4198
_cell_measurement_theta_min      2.57
_cell_measurement_theta_max      28.10

_exptl_crystal_description       BLOCK
_exptl_crystal_colour            COLOURLESS
_exptl_crystal_size_max          0.20
_exptl_crystal_size_mid          0.12
_exptl_crystal_size_min          0.06
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.622
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             792
_exptl_absorpt_coefficient_mu    0.879
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.8411
_exptl_absorpt_correction_T_max  0.9467
_exptl_absorpt_process_details   sadabs

_exptl_special_details           
;
?
;

_diffrn_ambient_temperature      291(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            13396
_diffrn_reflns_av_R_equivalents  0.0244
_diffrn_reflns_av_sigmaI/netI    0.0236
_diffrn_reflns_limit_h_min       -20
_diffrn_reflns_limit_h_max       20
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_theta_min         2.57
_diffrn_reflns_theta_max         27.49
_reflns_number_total             3626
_reflns_number_gt                3007
_reflns_threshold_expression     >2sigma(I)

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

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

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0377P)²+1.2188P] where P=(Fo²+2Fc²)/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         3626
_refine_ls_number_parameters     251
_refine_ls_number_restraints     10
_refine_ls_R_factor_all          0.0435
_refine_ls_R_factor_gt           0.0342
_refine_ls_wR_factor_ref         0.0889
_refine_ls_wR_factor_gt          0.0830
_refine_ls_goodness_of_fit_ref   1.050
_refine_ls_restrained_S_all      1.050
_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
Mn1 Mn 0.125160(18) 0.43002(5) 0.332296(18) 0.02346(10) Uani 1 1 d . . .
O4 O 0.12846(9) 0.5869(2) 0.21728(9) 0.0310(3) Uani 1 1 d . . .
O5 O 0.14991(11) 0.5407(3) 0.08873(10) 0.0467(4) Uani 1 1 d . . .
O7 O 0.11772(9) 1.0366(2) 0.18567(10) 0.0324(3) Uani 1 1 d . . .
O6 O 0.20326(9) 1.1858(3) 0.29839(10) 0.0343(4) Uani 1 1 d . . .
O8 O 0.5000 1.2333(4) 0.2500 0.0915(14) Uani 1 2 d S . .
O3 O 0.0000 0.2581(3) 0.2500 0.0267(4) Uani 1 2 d SD . .
O1 O 0.04039(10) 0.6816(3) 0.35867(10) 0.0376(4) Uani 1 1 d D . .
O2 O 0.11352(12) 0.2479(3) 0.44283(11) 0.0414(4) Uani 1 1 d D . .
O9 O 0.04787(11) 0.2113(3) 0.02799(11) 0.0413(4) Uani 1 1 d D . .
N1 N 0.24412(11) 0.6089(3) 0.40743(11) 0.0321(4) Uani 1 1 d . . .
C1 C 0.17105(12) 0.6109(3) 0.16189(12) 0.0258(4) Uani 1 1 d . . .
C2 C 0.25539(12) 0.7274(3) 0.18523(12) 0.0241(4) Uani 1 1 d . . .
C3 C 0.32757(13) 0.6219(3) 0.16999(14) 0.0315(5) Uani 1 1 d . . .
H3 H 0.3217 0.4874 0.1444 0.038 Uiso 1 1 calc R . .
C4 C 0.40753(13) 0.7160(4) 0.19273(15) 0.0347(5) Uani 1 1 d . . .
H4 H 0.4553 0.6428 0.1838 0.042 Uiso 1 1 calc R . .
C5 C 0.41681(13) 0.9196(3) 0.22890(15) 0.0326(5) Uani 1 1 d . . .
C6 C 0.34441(13) 1.0252(3) 0.24276(14) 0.0300(4) Uani 1 1 d . . .
H6 H 0.3502 1.1618 0.2666 0.036 Uiso 1 1 calc R . .
C7 C 0.26407(12) 0.9319(3) 0.22199(12) 0.0245(4) Uani 1 1 d . . .
C8 C 0.5000 1.0384(5) 0.2500 0.0451(9) Uani 1 2 d S . .
C9 C 0.23924(16) 0.7990(4) 0.44436(17) 0.0466(6) Uani 1 1 d . . .
H9 H 0.1854 0.8494 0.4473 0.056 Uiso 1 1 calc R . .
C10 C 0.30899(18) 0.9246(5) 0.47828(19) 0.0551(7) Uani 1 1 d . . .
H10 H 0.3017 1.0531 0.5051 0.066 Uiso 1 1 calc R . .
C11 C 0.38913(17) 0.8604(5) 0.47251(16) 0.0481(6) Uani 1 1 d . . .
C12 C 0.39545(16) 0.6624(6) 0.43514(18) 0.0556(7) Uani 1 1 d . . .
H12 H 0.4487 0.6101 0.4309 0.067 Uiso 1 1 calc R . .
C13 C 0.32209(15) 0.5419(5) 0.40391(17) 0.0461(6) Uani 1 1 d . . .
H13 H 0.3278 0.4090 0.3796 0.055 Uiso 1 1 calc R . .
C14 C 0.46185(18) 1.0101(6) 0.5041(2) 0.0605(8) Uani 1 1 d . . .
H14 H 0.4499 1.1313 0.5330 0.073 Uiso 1 1 calc R . .
C15 C 0.18792(12) 1.0601(3) 0.23633(12) 0.0244(4) Uani 1 1 d . . .
H3WA H 0.0265(17) 0.177(4) 0.2247(17) 0.059(9) Uiso 1 1 d D . .
H1C H 0.0434(16) 0.721(5) 0.4079(8) 0.061(9) Uiso 1 1 d D . .
H1B H -0.0098(9) 0.667(5) 0.3328(14) 0.063(9) Uiso 1 1 d D . .
H2C H 0.1383(17) 0.308(5) 0.4882(13) 0.080(12) Uiso 1 1 d D . .
H2B H 0.0623(8) 0.228(6) 0.4450(19) 0.086(13) Uiso 1 1 d D . .
H9C H 0.0748(17) 0.322(2) 0.0470(16) 0.057(9) Uiso 1 1 d D . .
H9B H 0.0669(18) 0.108(3) 0.0596(15) 0.060(10) Uiso 1 1 d D . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Mn1 O6 2.1180(14) 1_545 ?
Mn1 O4 2.1204(14) . ?
Mn1 O2 2.1671(17) . ?
Mn1 O1 2.1769(16) . ?
Mn1 N1 2.3107(17) . ?
Mn1 O3 2.4032(10) . ?
O4 C1 1.254(2) . ?
O5 C1 1.242(3) . ?
O7 C15 1.248(2) . ?
O6 C15 1.257(2) . ?
O6 Mn1 2.1180(14) 1_565 ?
O8 C8 1.212(4) . ?
O3 Mn1 2.4032(10) 2 ?
O3 H3WA 0.827(10) . ?
O1 H1C 0.828(9) . ?
O1 H1B 0.826(9) . ?
O2 H2C 0.843(10) . ?
O2 H2B 0.839(10) . ?
O9 H9C 0.837(10) . ?
O9 H9B 0.838(10) . ?
N1 C13 1.332(3) . ?
N1 C9 1.336(3) . ?
C1 C2 1.507(3) . ?
C2 C7 1.399(3) . ?
C2 C3 1.400(3) . ?
C3 C4 1.384(3) . ?
C3 H3 0.9300 . ?
C4 C5 1.390(3) . ?
C4 H4 0.9300 . ?
C5 C6 1.395(3) . ?
C5 C8 1.497(3) . ?
C6 C7 1.385(3) . ?
C6 H6 0.9300 . ?
C7 C15 1.520(3) . ?
C8 C5 1.497(3) 2_655 ?
C9 C10 1.376(3) . ?
C9 H9 0.9300 . ?
C10 C11 1.369(4) . ?
C10 H10 0.9300 . ?
C11 C12 1.387(4) . ?
C11 C14 1.492(4) . ?
C12 C13 1.393(4) . ?
C12 H12 0.9300 . ?
C13 H13 0.9300 . ?
C14 C14 1.267(6) 3_676 ?
C14 H14 0.9300 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
O6 Mn1 O4 88.20(6) 1_545 . ?
O6 Mn1 O2 90.33(7) 1_545 . ?
O4 Mn1 O2 174.57(7) . . ?
O6 Mn1 O1 176.29(6) 1_545 . ?
O4 Mn1 O1 88.95(6) . . ?
O2 Mn1 O1 92.29(7) . . ?
O6 Mn1 N1 90.93(6) 1_545 . ?
O4 Mn1 N1 93.78(6) . . ?
O2 Mn1 N1 91.48(7) . . ?
O1 Mn1 N1 91.63(7) . . ?
O6 Mn1 O3 90.30(6) 1_545 . ?
O4 Mn1 O3 83.94(5) . . ?
O2 Mn1 O3 90.84(6) . . ?
O1 Mn1 O3 87.04(6) . . ?
N1 Mn1 O3 177.37(6) . . ?
C1 O4 Mn1 144.32(14) . . ?
C15 O6 Mn1 129.26(13) . 1_565 ?
Mn1 O3 Mn1 127.15(9) . 2 ?
Mn1 O3 H3WA 95(2) . . ?
Mn1 O3 H3WA 117(2) 2 . ?
Mn1 O1 H1C 120(2) . . ?
Mn1 O1 H1B 114(2) . . ?
H1C O1 H1B 111.5(16) . . ?
Mn1 O2 H2C 113(2) . . ?
Mn1 O2 H2B 112(2) . . ?
H2C O2 H2B 107.7(16) . . ?
H9C O9 H9B 108.7(15) . . ?
C13 N1 C9 116.4(2) . . ?
C13 N1 Mn1 120.01(16) . . ?
C9 N1 Mn1 122.69(15) . . ?
O5 C1 O4 124.71(19) . . ?
O5 C1 C2 116.73(18) . . ?
O4 C1 C2 118.54(18) . . ?
C7 C2 C3 119.58(18) . . ?
C7 C2 C1 122.91(17) . . ?
C3 C2 C1 117.50(18) . . ?
C4 C3 C2 120.56(19) . . ?
C4 C3 H3 119.7 . . ?
C2 C3 H3 119.7 . . ?
C3 C4 C5 120.30(19) . . ?
C3 C4 H4 119.9 . . ?
C5 C4 H4 119.9 . . ?
C4 C5 C6 118.82(19) . . ?
C4 C5 C8 123.56(19) . . ?
C6 C5 C8 117.5(2) . . ?
C7 C6 C5 121.75(19) . . ?
C7 C6 H6 119.1 . . ?
C5 C6 H6 119.1 . . ?
C6 C7 C2 118.97(18) . . ?
C6 C7 C15 118.60(18) . . ?
C2 C7 C15 122.37(17) . . ?
O8 C8 C5 119.56(14) . 2_655 ?
O8 C8 C5 119.56(14) . . ?
C5 C8 C5 120.9(3) 2_655 . ?
N1 C9 C10 124.0(2) . . ?
N1 C9 H9 118.0 . . ?
C10 C9 H9 118.0 . . ?
C11 C10 C9 120.0(3) . . ?
C11 C10 H10 120.0 . . ?
C9 C10 H10 120.0 . . ?
C10 C11 C12 116.7(2) . . ?
C10 C11 C14 117.9(3) . . ?
C12 C11 C14 125.3(3) . . ?
C11 C12 C13 120.0(2) . . ?
C11 C12 H12 120.0 . . ?
C13 C12 H12 120.0 . . ?
N1 C13 C12 122.8(2) . . ?
N1 C13 H13 118.6 . . ?
C12 C13 H13 118.6 . . ?
C14 C14 C11 127.0(4) 3_676 . ?
C14 C14 H14 116.5 3_676 . ?
C11 C14 H14 116.5 . . ?
O7 C15 O6 126.21(18) . . ?
O7 C15 C7 118.40(17) . . ?
O6 C15 C7 115.36(17) . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
O6 Mn1 O4 C1 -26.1(2) 1_545 . . . ?
O2 Mn1 O4 C1 -100.5(7) . . . . ?
O1 Mn1 O4 C1 156.3(2) . . . . ?
N1 Mn1 O4 C1 64.7(2) . . . . ?
O3 Mn1 O4 C1 -116.6(2) . . . . ?
O6 Mn1 O3 Mn1 -143.45(5) 1_545 . . 2 ?
O4 Mn1 O3 Mn1 -55.29(4) . . . 2 ?
O2 Mn1 O3 Mn1 126.22(5) . . . 2 ?
O1 Mn1 O3 Mn1 33.97(5) . . . 2 ?
N1 Mn1 O3 Mn1 -25.6(11) . . . 2 ?
O6 Mn1 N1 C13 7.17(19) 1_545 . . . ?
O4 Mn1 N1 C13 -81.09(19) . . . . ?
O2 Mn1 N1 C13 97.5(2) . . . . ?
O1 Mn1 N1 C13 -170.14(19) . . . . ?
O3 Mn1 N1 C13 -110.7(11) . . . . ?
O6 Mn1 N1 C9 176.2(2) 1_545 . . . ?
O4 Mn1 N1 C9 87.9(2) . . . . ?
O2 Mn1 N1 C9 -93.5(2) . . . . ?
O1 Mn1 N1 C9 -1.1(2) . . . . ?
O3 Mn1 N1 C9 58.3(12) . . . . ?
Mn1 O4 C1 O5 110.2(3) . . . . ?
Mn1 O4 C1 C2 -67.9(3) . . . . ?
O5 C1 C2 C7 128.3(2) . . . . ?
O4 C1 C2 C7 -53.4(3) . . . . ?
O5 C1 C2 C3 -52.6(3) . . . . ?
O4 C1 C2 C3 125.6(2) . . . . ?
C7 C2 C3 C4 1.5(3) . . . . ?
C1 C2 C3 C4 -177.6(2) . . . . ?
C2 C3 C4 C5 -1.8(4) . . . . ?
C3 C4 C5 C6 0.9(4) . . . . ?
C3 C4 C5 C8 -175.8(2) . . . . ?
C4 C5 C6 C7 0.4(3) . . . . ?
C8 C5 C6 C7 177.33(19) . . . . ?
C5 C6 C7 C2 -0.8(3) . . . . ?
C5 C6 C7 C15 -178.0(2) . . . . ?
C3 C2 C7 C6 -0.2(3) . . . . ?
C1 C2 C7 C6 178.85(19) . . . . ?
C3 C2 C7 C15 176.91(18) . . . . ?
C1 C2 C7 C15 -4.0(3) . . . . ?
C4 C5 C8 O8 151.68(18) . . . . ?
C6 C5 C8 O8 -25.0(2) . . . . ?
C4 C5 C8 C5 -28.32(18) . . . 2_655 ?
C6 C5 C8 C5 155.0(2) . . . 2_655 ?
C13 N1 C9 C10 -0.3(4) . . . . ?
Mn1 N1 C9 C10 -169.6(2) . . . . ?
N1 C9 C10 C11 2.4(5) . . . . ?
C9 C10 C11 C12 -2.9(4) . . . . ?
C9 C10 C11 C14 175.2(3) . . . . ?
C10 C11 C12 C13 1.5(4) . . . . ?
C14 C11 C12 C13 -176.5(3) . . . . ?
C9 N1 C13 C12 -1.2(4) . . . . ?
Mn1 N1 C13 C12 168.4(2) . . . . ?
C11 C12 C13 N1 0.6(5) . . . . ?
C10 C11 C14 C14 -171.7(5) . . . 3_676 ?
C12 C11 C14 C14 6.3(7) . . . 3_676 ?
Mn1 O6 C15 O7 -8.9(3) 1_565 . . . ?
Mn1 O6 C15 C7 169.19(13) 1_565 . . . ?
C6 C7 C15 O7 145.6(2) . . . . ?
C2 C7 C15 O7 -31.5(3) . . . . ?
C6 C7 C15 O6 -32.7(3) . . . . ?
C2 C7 C15 O6 150.20(19) . . . . ?

_diffrn_measured_fraction_theta_max 0.998
_diffrn_reflns_theta_full        27.49
_diffrn_measured_fraction_theta_full 0.998
_refine_diff_density_max         1.150
_refine_diff_density_min         -0.413
_refine_diff_density_rms         0.060


# Attachment 'compound_1.cif'

data_1
_database_code_depnum_ccdc_archive 'CCDC 673351'

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C29 H22 Cu N2 O10'
_chemical_formula_weight         622.03

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cu Cu 0.3201 1.2651 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_symmetry_cell_setting           Monoclinic
_symmetry_space_group_name_H-M   C2/c

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

_cell_length_a                   24.098(7)
_cell_length_b                   11.347(3)
_cell_length_c                   9.692(2)
_cell_angle_alpha                90.00
_cell_angle_beta                 99.173(7)
_cell_angle_gamma                90.00
_cell_volume                     2616.2(11)
_cell_formula_units_Z            4
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    ?
_cell_measurement_theta_min      1.99
_cell_measurement_theta_max      25.10

_exptl_crystal_description       block
_exptl_crystal_colour            blue
_exptl_crystal_size_max          0.21
_exptl_crystal_size_mid          0.18
_exptl_crystal_size_min          0.10
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.579
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1276
_exptl_absorpt_coefficient_mu    0.901
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.8341
_exptl_absorpt_correction_T_max  0.9137
_exptl_absorpt_process_details   sadabs

_exptl_special_details           
;
?
;

_diffrn_ambient_temperature      296(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            6464
_diffrn_reflns_av_R_equivalents  0.0478
_diffrn_reflns_av_sigmaI/netI    0.0719
_diffrn_reflns_limit_h_min       -26
_diffrn_reflns_limit_h_max       28
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_theta_min         1.99
_diffrn_reflns_theta_max         25.10
_reflns_number_total             2322
_reflns_number_gt                1457
_reflns_threshold_expression     >2sigma(I)

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

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

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0370P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         2322
_refine_ls_number_parameters     226
_refine_ls_number_restraints     6
_refine_ls_R_factor_all          0.0683
_refine_ls_R_factor_gt           0.0418
_refine_ls_wR_factor_ref         0.0884
_refine_ls_wR_factor_gt          0.0846
_refine_ls_goodness_of_fit_ref   0.992
_refine_ls_restrained_S_all      0.998
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
Cu1 Cu 0.0000 0.0000 0.0000 0.03249(19) Uani 1 2 d S . .
N1 N 0.07566(10) -0.0775(2) 0.0138(3) 0.0326(7) Uani 1 1 d . . .
O1 O 0.0000 -0.0612(3) 0.2500 0.0413(9) Uani 1 2 d S . .
O2 O 0.03385(8) 0.15017(18) 0.0669(2) 0.0337(6) Uani 1 1 d . . .
O3 O 0.09108(10) 0.1832(2) -0.0901(2) 0.0480(7) Uani 1 1 d . . .
O6 O 0.0000 0.6696(3) 0.2500 0.0565(10) Uani 1 2 d S . .
C1 C 0.08712(14) -0.1505(3) -0.0863(4) 0.0430(9) Uani 1 1 d . . .
H1 H 0.0593 -0.1652 -0.1625 0.052 Uiso 1 1 calc R . .
C2 C 0.13824(17) -0.2043(4) -0.0805(4) 0.0751(14) Uani 1 1 d . . .
H2 H 0.1449 -0.2522 -0.1540 0.090 Uiso 1 1 calc R . .
C3 C 0.17976(17) -0.1884(5) 0.0319(4) 0.0852(16) Uani 1 1 d . . .
C4 C 0.16825(15) -0.1123(4) 0.1339(4) 0.0717(13) Uani 1 1 d . . .
H4A H 0.1956 -0.0964 0.2108 0.086 Uiso 1 1 calc R . .
C5 C 0.11639(14) -0.0596(3) 0.1223(4) 0.0472(9) Uani 1 1 d . . .
H5 H 0.1094 -0.0092 0.1932 0.057 Uiso 1 1 calc R . .
C6 C 0.2441(5) -0.204(2) 0.0456(19) 0.063(4) Uani 0.395(17) 1 d PU . 1
H6A H 0.2611 -0.1309 0.0209 0.075 Uiso 0.395(17) 1 calc PR . 1
H6B H 0.2598 -0.2232 0.1413 0.075 Uiso 0.395(17) 1 calc PR . 1
C6' C 0.2314(4) -0.2813(12) 0.0439(11) 0.063(3) Uani 0.605(17) 1 d PU . 2
H6'1 H 0.2498 -0.2910 0.1398 0.075 Uiso 0.605(17) 1 calc PR . 2
H6'2 H 0.2192 -0.3575 0.0051 0.075 Uiso 0.605(17) 1 calc PR . 2
C7 C 0.06890(13) 0.2112(3) 0.0110(3) 0.0347(8) Uani 1 1 d . . .
C8 C 0.08145(13) 0.3303(3) 0.0796(3) 0.0312(8) Uani 1 1 d . . .
C9 C 0.13353(14) 0.3866(3) 0.0879(3) 0.0385(9) Uani 1 1 d . A .
C10 C 0.14072(14) 0.4971(3) 0.1484(4) 0.0486(9) Uani 1 1 d . . .
H10 H 0.1753 0.5349 0.1538 0.058 Uiso 1 1 calc R . .
C11 C 0.09748(15) 0.5521(3) 0.2007(4) 0.0469(9) Uani 1 1 d . . .
H11 H 0.1031 0.6267 0.2404 0.056 Uiso 1 1 calc R . .
C12 C 0.04598(12) 0.4977(3) 0.1950(3) 0.0332(7) Uani 1 1 d . . .
C13 C 0.03861(13) 0.3874(3) 0.1346(3) 0.0334(8) Uani 1 1 d . . .
H13 H 0.0040 0.3501 0.1306 0.040 Uiso 1 1 calc R . .
C14 C 0.18371(16) 0.3289(4) 0.0414(5) 0.0529(11) Uani 1 1 d . . .
C15 C 0.0000 0.5621(4) 0.2500 0.0353(11) Uani 1 2 d S . .
O4 O 0.19661(13) 0.2251(3) 0.0981(4) 0.0578(13) Uani 0.802(5) 1 d P A 1
H4 H 0.2256 0.2009 0.0734 0.087 Uiso 0.802(5) 1 calc PR A 1
O5 O 0.2101(2) 0.3796(4) -0.0358(5) 0.0670(15) Uani 0.802(5) 1 d P A 1
O4' O 0.1818(6) 0.2745(14) -0.0774(15) 0.072(6) Uani 0.198(5) 1 d P A 2
H4' H 0.1496 0.2762 -0.1201 0.109 Uiso 0.198(5) 1 calc PR A 2
O5' O 0.2301(7) 0.3989(18) 0.048(2) 0.069(6) Uani 0.198(5) 1 d P A 2
H1W H -0.0260(15) -0.102(3) 0.219(4) 0.082 Uiso 1 1 d . . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Cu1 O2 1.955(2) 5 ?
Cu1 O2 1.955(2) . ?
Cu1 N1 2.010(2) 5 ?
Cu1 N1 2.010(2) . ?
Cu1 O1 2.5206(11) . ?
N1 C5 1.334(4) . ?
N1 C1 1.337(4) . ?
O1 H1W 0.80(3) . ?
O2 C7 1.278(4) . ?
O3 C7 1.231(4) . ?
O6 C15 1.220(5) . ?
C1 C2 1.368(5) . ?
C1 H1 0.9300 . ?
C2 C3 1.369(5) . ?
C2 H2 0.9300 . ?
C3 C4 1.373(5) . ?
C3 C6 1.545(12) . ?
C3 C6' 1.620(10) . ?
C4 C5 1.374(5) . ?
C4 H4A 0.9300 . ?
C5 H5 0.9300 . ?
C6 C6 1.43(4) 7_545 ?
C6 H6A 0.9700 . ?
C6 H6B 0.9700 . ?
C6' C6' 1.51(2) 7_545 ?
C6' H6'1 0.9700 . ?
C6' H6'2 0.9700 . ?
C7 C8 1.515(4) . ?
C8 C13 1.395(4) . ?
C8 C9 1.399(4) . ?
C9 C10 1.383(4) . ?
C9 C14 1.506(5) . ?
C10 C11 1.379(4) . ?
C10 H10 0.9300 . ?
C11 C12 1.379(4) . ?
C11 H11 0.9300 . ?
C12 C13 1.381(4) . ?
C12 C15 1.495(4) . ?
C13 H13 0.9300 . ?
C14 O5 1.203(6) . ?
C14 O4' 1.301(14) . ?
C14 O4 1.316(5) . ?
C14 O5' 1.364(18) . ?
C15 C12 1.495(4) 2 ?
O4 H4 0.8200 . ?
O4' H4' 0.8200 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
O2 Cu1 O2 180.00(18) 5 . ?
O2 Cu1 N1 91.91(9) 5 5 ?
O2 Cu1 N1 88.09(9) . 5 ?
O2 Cu1 N1 88.09(9) 5 . ?
O2 Cu1 N1 91.91(9) . . ?
N1 Cu1 N1 180.00(14) 5 . ?
O2 Cu1 O1 90.86(9) 5 . ?
O2 Cu1 O1 89.14(9) . . ?
N1 Cu1 O1 92.62(8) 5 . ?
N1 Cu1 O1 87.38(8) . . ?
C5 N1 C1 117.1(3) . . ?
C5 N1 Cu1 122.1(2) . . ?
C1 N1 Cu1 120.8(2) . . ?
Cu1 O1 H1W 86(3) . . ?
C7 O2 Cu1 126.9(2) . . ?
N1 C1 C2 122.4(3) . . ?
N1 C1 H1 118.8 . . ?
C2 C1 H1 118.8 . . ?
C1 C2 C3 120.8(4) . . ?
C1 C2 H2 119.6 . . ?
C3 C2 H2 119.6 . . ?
C2 C3 C4 116.7(4) . . ?
C2 C3 C6 130.5(8) . . ?
C4 C3 C6 109.0(8) . . ?
C2 C3 C6' 115.3(6) . . ?
C4 C3 C6' 126.7(5) . . ?
C6 C3 C6' 34.1(5) . . ?
C5 C4 C3 120.0(4) . . ?
C5 C4 H4A 120.0 . . ?
C3 C4 H4A 120.0 . . ?
N1 C5 C4 122.9(3) . . ?
N1 C5 H5 118.5 . . ?
C4 C5 H5 118.5 . . ?
C6 C6 C3 109.0(15) 7_545 . ?
C6 C6 H6A 109.9 7_545 . ?
C3 C6 H6A 109.9 . . ?
C6 C6 H6B 109.9 7_545 . ?
C3 C6 H6B 109.9 . . ?
H6A C6 H6B 108.3 . . ?
C6' C6' C3 99.9(9) 7_545 . ?
C6' C6' H6'1 111.8 7_545 . ?
C3 C6' H6'1 111.8 . . ?
C6' C6' H6'2 111.8 7_545 . ?
C3 C6' H6'2 111.8 . . ?
H6'1 C6' H6'2 109.5 . . ?
O3 C7 O2 126.7(3) . . ?
O3 C7 C8 119.9(3) . . ?
O2 C7 C8 113.4(3) . . ?
C13 C8 C9 118.5(3) . . ?
C13 C8 C7 118.3(3) . . ?
C9 C8 C7 123.2(3) . . ?
C10 C9 C8 119.3(3) . . ?
C10 C9 C14 117.9(3) . . ?
C8 C9 C14 122.7(3) . . ?
C11 C10 C9 121.0(3) . . ?
C11 C10 H10 119.5 . . ?
C9 C10 H10 119.5 . . ?
C10 C11 C12 120.7(3) . . ?
C10 C11 H11 119.7 . . ?
C12 C11 H11 119.7 . . ?
C11 C12 C13 118.5(3) . . ?
C11 C12 C15 118.7(3) . . ?
C13 C12 C15 122.8(3) . . ?
C12 C13 C8 122.0(3) . . ?
C12 C13 H13 119.0 . . ?
C8 C13 H13 119.0 . . ?
O5 C14 O4' 67.9(8) . . ?
O5 C14 O4 125.0(4) . . ?
O4' C14 O4 85.2(8) . . ?
O5 C14 O5' 40.4(9) . . ?
O4' C14 O5' 103.2(12) . . ?
O4 C14 O5' 111.4(10) . . ?
O5 C14 C9 120.6(4) . . ?
O4' C14 C9 123.7(7) . . ?
O4 C14 C9 114.3(4) . . ?
O5' C14 C9 115.1(9) . . ?
O6 C15 C12 119.3(2) . . ?
O6 C15 C12 119.3(2) . 2 ?
C12 C15 C12 121.5(4) . 2 ?
C14 O4 H4 109.5 . . ?
C14 O4' H4' 109.5 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
O2 Cu1 N1 C5 -137.8(3) 5 . . . ?
O2 Cu1 N1 C5 42.2(3) . . . . ?
N1 Cu1 N1 C5 50(69) 5 . . . ?
O1 Cu1 N1 C5 -46.9(3) . . . . ?
O2 Cu1 N1 C1 41.8(2) 5 . . . ?
O2 Cu1 N1 C1 -138.2(2) . . . . ?
N1 Cu1 N1 C1 -131(68) 5 . . . ?
O1 Cu1 N1 C1 132.7(3) . . . . ?
O2 Cu1 O2 C7 69(53) 5 . . . ?
N1 Cu1 O2 C7 -120.7(3) 5 . . . ?
N1 Cu1 O2 C7 59.3(3) . . . . ?
O1 Cu1 O2 C7 146.6(2) . . . . ?
C5 N1 C1 C2 -0.7(5) . . . . ?
Cu1 N1 C1 C2 179.7(3) . . . . ?
N1 C1 C2 C3 2.2(7) . . . . ?
C1 C2 C3 C4 -2.9(8) . . . . ?
C1 C2 C3 C6 -158.2(12) . . . . ?
C1 C2 C3 C6' 165.1(6) . . . . ?
C2 C3 C4 C5 2.3(8) . . . . ?
C6 C3 C4 C5 162.6(10) . . . . ?
C6' C3 C4 C5 -164.2(7) . . . . ?
C1 N1 C5 C4 0.0(5) . . . . ?
Cu1 N1 C5 C4 179.6(3) . . . . ?
C3 C4 C5 N1 -0.8(7) . . . . ?
C2 C3 C6 C6 -32(3) . . . 7_545 ?
C4 C3 C6 C6 171.1(19) . . . 7_545 ?
C6' C3 C6 C6 42.7(16) . . . 7_545 ?
C2 C3 C6' C6' 87.7(12) . . . 7_545 ?
C4 C3 C6' C6' -105.7(10) . . . 7_545 ?
C6 C3 C6' C6' -38.0(13) . . . 7_545 ?
Cu1 O2 C7 O3 -5.5(5) . . . . ?
Cu1 O2 C7 C8 173.03(18) . . . . ?
O3 C7 C8 C13 145.6(3) . . . . ?
O2 C7 C8 C13 -33.0(4) . . . . ?
O3 C7 C8 C9 -33.1(5) . . . . ?
O2 C7 C8 C9 148.3(3) . . . . ?
C13 C8 C9 C10 -0.8(5) . . . . ?
C7 C8 C9 C10 177.9(3) . . . . ?
C13 C8 C9 C14 175.4(3) . . . . ?
C7 C8 C9 C14 -5.9(5) . . . . ?
C8 C9 C10 C11 0.2(5) . . . . ?
C14 C9 C10 C11 -176.2(4) . . . . ?
C9 C10 C11 C12 0.5(5) . . . . ?
C10 C11 C12 C13 -0.5(5) . . . . ?
C10 C11 C12 C15 -178.5(3) . . . . ?
C11 C12 C13 C8 -0.2(5) . . . . ?
C15 C12 C13 C8 177.8(3) . . . . ?
C9 C8 C13 C12 0.8(5) . . . . ?
C7 C8 C13 C12 -177.9(3) . . . . ?
C10 C9 C14 O5 -53.7(6) . . . . ?
C8 C9 C14 O5 130.1(5) . . . . ?
C10 C9 C14 O4' -136.1(10) . . . . ?
C8 C9 C14 O4' 47.7(11) . . . . ?
C10 C9 C14 O4 122.8(4) . . . . ?
C8 C9 C14 O4 -53.4(5) . . . . ?
C10 C9 C14 O5' -8.1(13) . . . . ?
C8 C9 C14 O5' 175.7(11) . . . . ?
C11 C12 C15 O6 26.9(3) . . . . ?
C13 C12 C15 O6 -151.0(2) . . . . ?
C11 C12 C15 C12 -153.1(3) . . . 2 ?
C13 C12 C15 C12 29.0(2) . . . 2 ?

_diffrn_measured_fraction_theta_max 0.995
_diffrn_reflns_theta_full        25.10
_diffrn_measured_fraction_theta_full 0.995
_refine_diff_density_max         0.402
_refine_diff_density_min         -0.375
_refine_diff_density_rms         0.064

