# Supplementary Material (ESI) for Dalton Transactions
# This journal is (c) The Royal Society of Chemistry 2011


data_global
_journal_name_full               'Dalton Trans.'

_journal_coden_Cambridge         0222
_journal_volume                  ?
_journal_page_first              ?
_journal_year                    ?

_publ_contact_author_name        'Puterova, Zita'
_publ_contact_author_email       zita.puterova@gmail.com

_publ_section_title              
;
Synthesis, crystal structure and antiradical effect of copper(II)
Schiff base complexes containing five-, six- and unusual seven-membered rings
;
loop_
_publ_author_name
Z.Puterova
J.Valentova
Z.Bojkova
J.Kozisek
F.Devinsky

data_I
_database_code_depnum_ccdc_archive 'CCDC 784967'
#TrackingRef '- 1_CCDC784967.cif'

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C11 H15 Cu N O5'
_chemical_formula_sum            'C11 H15 Cu N O5'
_chemical_formula_weight         304.78

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   'P 21/n '
_symmetry_space_group_name_Hall  '-P 2yn '

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

_cell_length_a                   17.3438(12)
_cell_length_b                   6.9318(3)
_cell_length_c                   21.7275(14)
_cell_angle_alpha                90.000
_cell_angle_beta                 93.486(5)
_cell_angle_gamma                90.000
_cell_volume                     2607.3(3)
_cell_formula_units_Z            8
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    38736
_cell_measurement_theta_min      3.1160
_cell_measurement_theta_max      29.5519

_exptl_crystal_description       needle
_exptl_crystal_colour            'dark green'
_exptl_crystal_size_max          0.4266
_exptl_crystal_size_mid          0.0190
_exptl_crystal_size_min          0.0092
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.553
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1256
_exptl_absorpt_coefficient_mu    1.687
_exptl_absorpt_correction_type   analytical
_exptl_absorpt_process_details   
;
CrysAlis RED, Oxford Diffraction Ltd.,
Version 1.171.33.8 (release 02-06-2008 CrysAlis171 .NET)
(compiled Jun 3 2008,11:28:45)
Analytical numeric absorption correction using a multifaceted crystal
model based on expressions derived by R.C. Clark & J.S. Reid.
(Clark, R. C. & Reid, J. S. (1995). Acta Cryst. A51, 887-897)
;
_exptl_absorpt_correction_T_min  0.657
_exptl_absorpt_correction_T_max  0.933

_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  
;
Goniometer Xcalibur, detector: Ruby (Gemini Cu)
;
_diffrn_measurement_method       '\w scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         0
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  0
_diffrn_standards_decay_%        0
_diffrn_reflns_number            10433
_diffrn_reflns_av_R_equivalents  0.0000
_diffrn_reflns_av_sigmaI/netI    0.1087
_diffrn_reflns_limit_h_min       -21
_diffrn_reflns_limit_h_max       21
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_l_min       -27
_diffrn_reflns_limit_l_max       27
_diffrn_reflns_theta_min         4.14
_diffrn_reflns_theta_max         26.37
_reflns_number_total             10433
_reflns_number_gt                6376
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'CrysAlis CCD (Oxford Diffraction, 2010)'
_computing_cell_refinement       'CrysAlis CCD'
_computing_data_reduction        'CrysAlis RED (Oxford Diffraction, 2010)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_molecular_graphics    'DIAMOND (Brandenburg, 1998)'
_computing_publication_material  ' enCIFer (Allen et al., 2008)'

_refine_special_details          
;
Refinement of F^2^ against ALL reflections. The weighted R-factor wR and
goodness of fit S are based on F^2^, conventional R-factors R are based
on F, with F set to zero for negative F^2^. The threshold expression of
F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is
not relevant to the choice of reflections for refinement. R-factors based
on F^2^ are statistically about twice as large as those based on F, and R-
factors based on ALL data will be even larger.
The crystal studied was a non-merohedral twin, the refined ratio of the
twin components being 0.52 (1):0.48 (1).
Non-merohedral twin refinement with a ratio of twin components 0.598 and 0.402
was done.
;

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[\s^2^(Fo^2^)+(0.0000P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         10433
_refine_ls_number_parameters     350
_refine_ls_number_restraints     17
_refine_ls_R_factor_all          0.0481
_refine_ls_R_factor_gt           0.0272
_refine_ls_wR_factor_ref         0.0500
_refine_ls_wR_factor_gt          0.0478
_refine_ls_goodness_of_fit_ref   0.604
_refine_ls_restrained_S_all      0.654
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C 0.88076(12) 0.5678(3) 0.20672(10) 0.0297(5) Uani 1 1 d . . .
C2 C 0.88898(13) 0.4962(3) 0.26761(10) 0.0392(6) Uani 1 1 d . . .
H2 H 0.9223 0.5589 0.2962 0.047 Uiso 1 1 calc R . .
C3 C 0.84940(14) 0.3374(4) 0.28588(11) 0.0464(7) Uani 1 1 d . . .
H3 H 0.8546 0.2950 0.3265 0.056 Uiso 1 1 calc R . .
C4 C 0.80127(13) 0.2407(3) 0.24274(11) 0.0447(6) Uani 1 1 d . . .
H4 H 0.7757 0.1297 0.2543 0.054 Uiso 1 1 calc R . .
C5 C 0.79089(12) 0.3068(3) 0.18309(11) 0.0368(6) Uani 1 1 d . . .
H5 H 0.7590 0.2384 0.1549 0.044 Uiso 1 1 calc R . .
C6 C 0.82750(12) 0.4761(3) 0.16373(10) 0.0305(5) Uani 1 1 d . . .
C7 C 0.92811(12) 0.7283(3) 0.19112(10) 0.0322(5) Uani 1 1 d . . .
H7 H 0.9641 0.7715 0.2215 0.039 Uiso 1 1 calc R . .
C8 C 0.94075(12) 1.0968(3) 0.07525(10) 0.0288(5) Uani 1 1 d . . .
C9 C 0.98115(11) 0.9747(3) 0.12686(10) 0.0280(5) Uani 1 1 d . . .
C10 C 1.00316(14) 1.1012(3) 0.18278(10) 0.0448(7) Uani 1 1 d . . .
H10C H 1.0282 1.0236 0.2147 0.054 Uiso 1 1 calc R . .
H10B H 0.9574 1.1583 0.1977 0.054 Uiso 1 1 calc R . .
H10A H 1.0377 1.2011 0.1711 0.054 Uiso 1 1 calc R . .
C11 C 1.05319(12) 0.8843(3) 0.10180(11) 0.0424(6) Uani 1 1 d . . .
H11C H 1.0787 0.8052 0.1331 0.051 Uiso 1 1 calc R . .
H11B H 1.0876 0.9844 0.0901 0.051 Uiso 1 1 calc R . .
H11A H 1.0386 0.8065 0.0665 0.051 Uiso 1 1 calc R . .
C21 C 0.45439(13) 0.5026(3) 0.10567(10) 0.0335(6) Uani 1 1 d . . .
C22 C 0.52957(13) 0.4370(3) 0.12294(11) 0.0445(7) Uani 1 1 d . . .
H22 H 0.5556 0.4901 0.1576 0.053 Uiso 1 1 calc R . .
C23 C 0.56555(14) 0.2980(4) 0.09045(12) 0.0500(7) Uani 1 1 d . . .
H23 H 0.6152 0.2573 0.1027 0.060 Uiso 1 1 calc R . .
C24 C 0.52646(13) 0.2192(3) 0.03904(12) 0.0495(7) Uani 1 1 d . . .
H24 H 0.5504 0.1258 0.0161 0.059 Uiso 1 1 calc R . .
C25 C 0.45252(13) 0.2775(3) 0.02147(11) 0.0427(6) Uani 1 1 d . . .
H25 H 0.4271 0.2194 -0.0126 0.051 Uiso 1 1 calc R . .
C26 C 0.41419(12) 0.4217(3) 0.05319(10) 0.0318(6) Uani 1 1 d . . .
C27 C 0.42511(13) 0.6584(3) 0.14131(10) 0.0362(6) Uani 1 1 d . . .
H27 H 0.4553 0.6978 0.1759 0.043 Uiso 1 1 calc R . .
C28 C 0.28010(13) 1.0310(3) 0.12804(11) 0.0354(6) Uani 1 1 d . . .
C29 C 0.33456(13) 0.9055(3) 0.16891(10) 0.0329(5) Uani 1 1 d . . .
C30 C 0.40027(14) 1.0297(3) 0.19743(11) 0.0545(7) Uani 1 1 d . . .
H30C H 0.4341 0.9511 0.2235 0.065 Uiso 1 1 calc R . .
H30B H 0.3792 1.1311 0.2214 0.065 Uiso 1 1 calc R . .
H30A H 0.4288 1.0850 0.1653 0.065 Uiso 1 1 calc R . .
C31 C 0.28749(14) 0.8147(3) 0.21873(10) 0.0496(7) Uani 1 1 d . . .
H31C H 0.3206 0.7359 0.2453 0.060 Uiso 1 1 calc R . .
H31B H 0.2471 0.7365 0.1996 0.060 Uiso 1 1 calc R . .
H31A H 0.2652 0.9147 0.2425 0.060 Uiso 1 1 calc R . .
N1 N 0.92559(9) 0.8176(2) 0.13961(8) 0.0260(4) Uani 1 1 d . . .
N21 N 0.36126(10) 0.7476(2) 0.12976(7) 0.0300(4) Uani 1 1 d . . .
O1 O 0.81071(8) 0.54034(19) 0.10760(6) 0.0332(4) Uani 1 1 d . . .
O2 O 0.88094(8) 1.02697(19) 0.04650(7) 0.0335(4) Uani 1 1 d . . .
O3 O 0.96898(8) 1.2565(2) 0.06296(7) 0.0407(4) Uani 1 1 d . . .
O4 O 0.75251(8) 0.7957(2) 0.01937(7) 0.0368(4) Uani 1 1 d D . .
H4A H 0.7097(6) 0.7146(17) 0.0098(7) 0.044 Uiso 1 1 d D . .
H4B H 0.7385(7) 0.8805(19) -0.0141(6) 0.044 Uiso 1 1 d D . .
O5 O 0.90838(9) 0.5891(2) -0.00043(7) 0.0387(4) Uani 1 1 d D . .
H5A H 0.9376(8) 0.6805(14) -0.0067(7) 0.046 Uiso 1 1 d D . .
H5B H 0.9253(11) 0.5151(19) 0.0270(3) 0.046 Uiso 1 1 d D . .
O21 O 0.34469(8) 0.47566(19) 0.03253(7) 0.0356(4) Uani 1 1 d . . .
O22 O 0.25433(9) 0.95809(19) 0.07630(7) 0.0364(4) Uani 1 1 d . . .
O23 O 0.26182(11) 1.1897(2) 0.14656(7) 0.0617(5) Uani 1 1 d . . .
O24 O 0.23649(9) 0.7205(2) -0.02281(7) 0.0424(4) Uani 1 1 d D . .
H24A H 0.2022(9) 0.804(2) -0.0297(5) 0.051 Uiso 1 1 d D . .
H24B H 0.2307(11) 0.6275(15) -0.0467(5) 0.051 Uiso 1 1 d D . .
O25 O 0.19645(9) 0.5272(2) 0.10201(8) 0.0443(4) Uani 1 1 d D . .
H25A H 0.2136(6) 0.4223(16) 0.1164(9) 0.053 Uiso 1 1 d D . .
H25B H 0.1623(7) 0.494(3) 0.0754(4) 0.053 Uiso 1 1 d D . .
Cu1 Cu 0.846706(15) 0.77499(3) 0.074050(12) 0.02853(7) Uani 1 1 d D . .
Cu21 Cu 0.292591(15) 0.70080(4) 0.058058(12) 0.03146(7) Uani 1 1 d D . .

loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_23
_atom_site_aniso_U_13
_atom_site_aniso_U_12
C1 0.0312(13) 0.0280(12) 0.0297(14) 0.0043(11) -0.0002(11) 0.0015(11)
C2 0.0397(15) 0.0446(15) 0.0323(15) 0.0032(12) -0.0059(12) 0.0006(12)
C3 0.0484(16) 0.0537(17) 0.0376(15) 0.0194(13) 0.0050(13) 0.0051(13)
C4 0.0390(14) 0.0461(16) 0.0501(16) 0.0159(14) 0.0109(13) -0.0043(13)
C5 0.0363(13) 0.0341(13) 0.0399(14) 0.0035(12) 0.0020(11) -0.0053(12)
C6 0.0280(13) 0.0271(12) 0.0365(14) -0.0003(11) 0.0037(11) 0.0053(11)
C7 0.0263(12) 0.0370(13) 0.0324(13) -0.0027(12) -0.0063(10) -0.0007(11)
C8 0.0289(13) 0.0268(13) 0.0311(14) -0.0022(11) 0.0046(11) 0.0020(11)
C9 0.0246(12) 0.0270(12) 0.0322(13) -0.0011(11) 0.0010(11) -0.0027(10)
C10 0.0542(17) 0.0361(14) 0.0426(15) -0.0036(12) -0.0089(13) -0.0059(12)
C11 0.0327(14) 0.0419(14) 0.0524(16) 0.0028(13) 0.0009(12) 0.0032(12)
C21 0.0349(14) 0.0280(12) 0.0368(15) 0.0039(12) -0.0029(12) 0.0020(11)
C22 0.0383(15) 0.0441(15) 0.0493(17) 0.0022(13) -0.0118(13) 0.0035(13)
C23 0.0326(14) 0.0476(15) 0.0690(18) 0.0072(15) -0.0034(14) 0.0119(13)
C24 0.0475(16) 0.0358(13) 0.0656(18) -0.0024(14) 0.0076(14) 0.0137(13)
C25 0.0422(15) 0.0354(13) 0.0498(15) -0.0069(13) -0.0026(13) 0.0042(12)
C26 0.0312(14) 0.0237(12) 0.0402(15) 0.0055(11) -0.0003(12) 0.0011(11)
C27 0.0424(15) 0.0338(13) 0.0311(14) 0.0019(11) -0.0083(12) -0.0004(12)
C28 0.0438(15) 0.0294(13) 0.0328(15) 0.0050(12) 0.0017(12) 0.0038(12)
C29 0.0430(15) 0.0299(12) 0.0252(13) -0.0010(11) -0.0018(11) 0.0017(11)
C30 0.0587(18) 0.0458(15) 0.0572(18) -0.0118(14) -0.0103(15) 0.0007(14)
C31 0.0706(18) 0.0438(14) 0.0353(14) 0.0052(12) 0.0111(13) 0.0087(14)
N1 0.0257(10) 0.0259(9) 0.0263(10) 0.0045(8) -0.0003(8) 0.0023(8)
N21 0.0345(10) 0.0259(10) 0.0292(10) 0.0050(9) -0.0017(9) 0.0019(9)
O1 0.0425(10) 0.0296(8) 0.0264(9) 0.0048(7) -0.0064(8) -0.0100(7)
O2 0.0320(9) 0.0265(8) 0.0406(10) 0.0074(7) -0.0091(8) -0.0036(7)
O3 0.0377(9) 0.0322(9) 0.0517(10) 0.0106(8) -0.0028(8) -0.0094(7)
O4 0.0347(9) 0.0299(8) 0.0430(10) 0.0085(8) -0.0193(8) -0.0043(8)
O5 0.0353(10) 0.0342(9) 0.0464(10) 0.0069(8) 0.0013(8) -0.0013(8)
O21 0.0297(9) 0.0307(8) 0.0448(10) -0.0076(8) -0.0097(8) 0.0045(7)
O22 0.0466(10) 0.0275(8) 0.0335(10) 0.0000(8) -0.0107(8) 0.0050(7)
O23 0.1055(16) 0.0394(10) 0.0385(10) -0.0042(9) -0.0084(10) 0.0319(11)
O24 0.0505(10) 0.0296(9) 0.0441(10) -0.0075(8) -0.0212(9) 0.0114(8)
O25 0.0419(10) 0.0321(9) 0.0578(12) 0.0057(9) -0.0045(9) 0.0034(8)
Cu1 0.03018(15) 0.02543(14) 0.02911(14) 0.00298(13) -0.00522(12) -0.00269(12)
Cu21 0.03279(16) 0.02612(14) 0.03430(16) -0.00070(13) -0.00756(13) 0.00289(13)

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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
C1 C2 1.412(3) . ?
C1 C6 1.423(3) . ?
C1 C7 1.436(3) . ?
C2 C3 1.369(3) . ?
C2 H2 0.9300 . ?
C3 C4 1.389(3) . ?
C3 H3 0.9300 . ?
C4 C5 1.376(3) . ?
C4 H4 0.9300 . ?
C5 C6 1.410(3) . ?
C5 H5 0.9300 . ?
C6 O1 1.314(2) . ?
C7 N1 1.278(2) . ?
C7 H7 0.9300 . ?
C8 O3 1.246(2) . ?
C8 O2 1.273(2) . ?
C8 C9 1.540(3) . ?
C9 N1 1.491(2) . ?
C9 C11 1.527(3) . ?
C9 C10 1.528(3) . ?
C10 H10C 0.9600 . ?
C10 H10B 0.9600 . ?
C10 H10A 0.9600 . ?
C11 H11C 0.9600 . ?
C11 H11B 0.9600 . ?
C11 H11A 0.9600 . ?
C21 C22 1.410(3) . ?
C21 C26 1.416(3) . ?
C21 C27 1.439(3) . ?
C22 C23 1.368(3) . ?
C22 H22 0.9300 . ?
C23 C24 1.383(3) . ?
C23 H23 0.9300 . ?
C24 C25 1.376(3) . ?
C24 H24 0.9300 . ?
C25 C26 1.404(3) . ?
C25 H25 0.9300 . ?
C26 O21 1.315(2) . ?
C27 N21 1.280(2) . ?
C27 H27 0.9300 . ?
C28 O23 1.220(3) . ?
C28 O22 1.288(2) . ?
C28 C29 1.528(3) . ?
C29 N21 1.478(2) . ?
C29 C30 1.529(3) . ?
C29 C31 1.530(3) . ?
C30 H30C 0.9600 . ?
C30 H30B 0.9600 . ?
C30 H30A 0.9600 . ?
C31 H31C 0.9600 . ?
C31 H31B 0.9600 . ?
C31 H31A 0.9600 . ?
N1 Cu1 1.9368(16) . ?
N21 Cu21 1.9300(16) . ?
O1 Cu1 1.9032(13) . ?
O2 Cu1 1.9507(13) . ?
O4 Cu1 1.9661(13) . ?
O4 H4A 0.944(4) . ?
O4 H4B 0.955(4) . ?
O5 Cu1 2.3735(15) . ?
O5 H5A 0.827(5) . ?
O5 H5B 0.826(5) . ?
O21 Cu21 1.9028(14) . ?
O22 Cu21 1.9519(14) . ?
O24 Cu21 1.9608(14) . ?
O24 H24A 0.834(5) . ?
O24 H24B 0.830(5) . ?
O25 Cu21 2.3097(16) . ?
O25 H25A 0.838(5) . ?
O25 H25B 0.835(5) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C2 C1 C6 118.9(2) . . ?
C2 C1 C7 117.8(2) . . ?
C6 C1 C7 123.29(19) . . ?
C3 C2 C1 122.0(2) . . ?
C3 C2 H2 119.0 . . ?
C1 C2 H2 119.0 . . ?
C2 C3 C4 118.9(2) . . ?
C2 C3 H3 120.5 . . ?
C4 C3 H3 120.5 . . ?
C5 C4 C3 120.9(2) . . ?
C5 C4 H4 119.6 . . ?
C3 C4 H4 119.6 . . ?
C4 C5 C6 121.5(2) . . ?
C4 C5 H5 119.2 . . ?
C6 C5 H5 119.2 . . ?
O1 C6 C5 118.7(2) . . ?
O1 C6 C1 123.79(19) . . ?
C5 C6 C1 117.5(2) . . ?
N1 C7 C1 126.37(19) . . ?
N1 C7 H7 116.8 . . ?
C1 C7 H7 116.8 . . ?
O3 C8 O2 123.5(2) . . ?
O3 C8 C9 118.52(19) . . ?
O2 C8 C9 117.98(18) . . ?
N1 C9 C11 108.59(16) . . ?
N1 C9 C10 113.85(17) . . ?
C11 C9 C10 110.40(17) . . ?
N1 C9 C8 105.44(16) . . ?
C11 C9 C8 108.18(17) . . ?
C10 C9 C8 110.13(17) . . ?
C9 C10 H10C 109.5 . . ?
C9 C10 H10B 109.5 . . ?
H10C C10 H10B 109.5 . . ?
C9 C10 H10A 109.5 . . ?
H10C C10 H10A 109.5 . . ?
H10B C10 H10A 109.5 . . ?
C9 C11 H11C 109.5 . . ?
C9 C11 H11B 109.5 . . ?
H11C C11 H11B 109.5 . . ?
C9 C11 H11A 109.5 . . ?
H11C C11 H11A 109.5 . . ?
H11B C11 H11A 109.5 . . ?
C22 C21 C26 119.3(2) . . ?
C22 C21 C27 116.7(2) . . ?
C26 C21 C27 123.9(2) . . ?
C23 C22 C21 122.2(2) . . ?
C23 C22 H22 118.9 . . ?
C21 C22 H22 118.9 . . ?
C22 C23 C24 118.6(2) . . ?
C22 C23 H23 120.7 . . ?
C24 C23 H23 120.7 . . ?
C25 C24 C23 120.7(2) . . ?
C25 C24 H24 119.6 . . ?
C23 C24 H24 119.6 . . ?
C24 C25 C26 122.3(2) . . ?
C24 C25 H25 118.9 . . ?
C26 C25 H25 118.9 . . ?
O21 C26 C25 119.1(2) . . ?
O21 C26 C21 124.0(2) . . ?
C25 C26 C21 116.9(2) . . ?
N21 C27 C21 125.9(2) . . ?
N21 C27 H27 117.0 . . ?
C21 C27 H27 117.0 . . ?
O23 C28 O22 124.0(2) . . ?
O23 C28 C29 119.0(2) . . ?
O22 C28 C29 116.95(19) . . ?
N21 C29 C28 106.93(17) . . ?
N21 C29 C30 113.47(18) . . ?
C28 C29 C30 109.51(18) . . ?
N21 C29 C31 107.56(17) . . ?
C28 C29 C31 107.93(19) . . ?
C30 C29 C31 111.20(19) . . ?
C29 C30 H30C 109.5 . . ?
C29 C30 H30B 109.5 . . ?
H30C C30 H30B 109.5 . . ?
C29 C30 H30A 109.5 . . ?
H30C C30 H30A 109.5 . . ?
H30B C30 H30A 109.5 . . ?
C29 C31 H31C 109.5 . . ?
C29 C31 H31B 109.5 . . ?
H31C C31 H31B 109.5 . . ?
C29 C31 H31A 109.5 . . ?
H31C C31 H31A 109.5 . . ?
H31B C31 H31A 109.5 . . ?
C7 N1 C9 121.92(17) . . ?
C7 N1 Cu1 123.73(14) . . ?
C9 N1 Cu1 114.24(12) . . ?
C27 N21 C29 122.86(18) . . ?
C27 N21 Cu21 124.14(15) . . ?
C29 N21 Cu21 112.93(13) . . ?
C6 O1 Cu1 125.86(13) . . ?
C8 O2 Cu1 116.35(13) . . ?
Cu1 O4 H4A 134.6(6) . . ?
Cu1 O4 H4B 132.0(6) . . ?
H4A O4 H4B 92.2(5) . . ?
Cu1 O5 H5A 90.1(4) . . ?
Cu1 O5 H5B 90.0(4) . . ?
H5A O5 H5B 114(2) . . ?
C26 O21 Cu21 125.13(13) . . ?
C28 O22 Cu21 115.58(14) . . ?
Cu21 O24 H24A 121.3(7) . . ?
Cu21 O24 H24B 122.7(7) . . ?
H24A O24 H24B 111.4(12) . . ?
Cu21 O25 H25A 110.9(6) . . ?
Cu21 O25 H25B 111.0(6) . . ?
H25A O25 H25B 104(2) . . ?
O1 Cu1 N1 94.72(6) . . ?
O1 Cu1 O2 174.80(6) . . ?
N1 Cu1 O2 82.79(6) . . ?
O1 Cu1 O4 90.81(6) . . ?
N1 Cu1 O4 163.17(7) . . ?
O2 Cu1 O4 90.36(6) . . ?
O1 Cu1 O5 88.23(6) . . ?
N1 Cu1 O5 104.88(6) . . ?
O2 Cu1 O5 96.81(6) . . ?
O4 Cu1 O5 91.16(6) . . ?
O21 Cu21 N21 95.31(7) . . ?
O21 Cu21 O22 169.08(6) . . ?
N21 Cu21 O22 83.29(7) . . ?
O21 Cu21 O24 90.84(6) . . ?
N21 Cu21 O24 163.69(7) . . ?
O22 Cu21 O24 87.81(6) . . ?
O21 Cu21 O25 93.48(6) . . ?
N21 Cu21 O25 100.34(7) . . ?
O22 Cu21 O25 97.43(6) . . ?
O24 Cu21 O25 94.33(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
C6 C1 C2 C3 2.4(3) . . . . ?
C7 C1 C2 C3 -176.4(2) . . . . ?
C1 C2 C3 C4 1.8(3) . . . . ?
C2 C3 C4 C5 -2.5(4) . . . . ?
C3 C4 C5 C6 -1.0(4) . . . . ?
C4 C5 C6 O1 -174.8(2) . . . . ?
C4 C5 C6 C1 5.1(3) . . . . ?
C2 C1 C6 O1 174.18(19) . . . . ?
C7 C1 C6 O1 -7.0(3) . . . . ?
C2 C1 C6 C5 -5.7(3) . . . . ?
C7 C1 C6 C5 173.08(19) . . . . ?
C2 C1 C7 N1 -176.1(2) . . . . ?
C6 C1 C7 N1 5.1(3) . . . . ?
O3 C8 C9 N1 167.95(18) . . . . ?
O2 C8 C9 N1 -13.5(2) . . . . ?
O3 C8 C9 C11 -76.0(2) . . . . ?
O2 C8 C9 C11 102.6(2) . . . . ?
O3 C8 C9 C10 44.7(3) . . . . ?
O2 C8 C9 C10 -136.7(2) . . . . ?
C26 C21 C22 C23 0.4(3) . . . . ?
C27 C21 C22 C23 -176.0(2) . . . . ?
C21 C22 C23 C24 -0.2(4) . . . . ?
C22 C23 C24 C25 -0.9(4) . . . . ?
C23 C24 C25 C26 1.8(4) . . . . ?
C24 C25 C26 O21 177.4(2) . . . . ?
C24 C25 C26 C21 -1.6(3) . . . . ?
C22 C21 C26 O21 -178.5(2) . . . . ?
C27 C21 C26 O21 -2.3(3) . . . . ?
C22 C21 C26 C25 0.4(3) . . . . ?
C27 C21 C26 C25 176.6(2) . . . . ?
C22 C21 C27 N21 173.9(2) . . . . ?
C26 C21 C27 N21 -2.3(4) . . . . ?
O23 C28 C29 N21 -166.5(2) . . . . ?
O22 C28 C29 N21 15.7(3) . . . . ?
O23 C28 C29 C30 -43.1(3) . . . . ?
O22 C28 C29 C30 139.0(2) . . . . ?
O23 C28 C29 C31 78.0(3) . . . . ?
O22 C28 C29 C31 -99.8(2) . . . . ?
C1 C7 N1 C9 -175.85(18) . . . . ?
C1 C7 N1 Cu1 8.4(3) . . . . ?
C11 C9 N1 C7 87.1(2) . . . . ?
C10 C9 N1 C7 -36.3(3) . . . . ?
C8 C9 N1 C7 -157.12(19) . . . . ?
C11 C9 N1 Cu1 -96.71(16) . . . . ?
C10 C9 N1 Cu1 139.87(15) . . . . ?
C8 C9 N1 Cu1 19.03(19) . . . . ?
C21 C27 N21 C29 179.41(19) . . . . ?
C21 C27 N21 Cu21 -3.8(3) . . . . ?
C28 C29 N21 C27 154.9(2) . . . . ?
C30 C29 N21 C27 34.1(3) . . . . ?
C31 C29 N21 C27 -89.4(2) . . . . ?
C28 C29 N21 Cu21 -22.2(2) . . . . ?
C30 C29 N21 Cu21 -143.01(16) . . . . ?
C31 C29 N21 Cu21 93.56(17) . . . . ?
C5 C6 O1 Cu1 174.81(14) . . . . ?
C1 C6 O1 Cu1 -5.1(3) . . . . ?
O3 C8 O2 Cu1 -179.63(16) . . . . ?
C9 C8 O2 Cu1 1.9(2) . . . . ?
C25 C26 O21 Cu21 -166.34(15) . . . . ?
C21 C26 O21 Cu21 12.6(3) . . . . ?
O23 C28 O22 Cu21 -179.68(19) . . . . ?
C29 C28 O22 Cu21 -1.9(2) . . . . ?
C6 O1 Cu1 N1 13.45(17) . . . . ?
C6 O1 Cu1 O2 -47.7(7) . . . . ?
C6 O1 Cu1 O4 -150.64(16) . . . . ?
C6 O1 Cu1 O5 118.23(16) . . . . ?
C7 N1 Cu1 O1 -14.89(18) . . . . ?
C9 N1 Cu1 O1 169.03(13) . . . . ?
C7 N1 Cu1 O2 160.52(18) . . . . ?
C9 N1 Cu1 O2 -15.56(13) . . . . ?
C7 N1 Cu1 O4 93.9(3) . . . . ?
C9 N1 Cu1 O4 -82.2(3) . . . . ?
C7 N1 Cu1 O5 -104.31(18) . . . . ?
C9 N1 Cu1 O5 79.61(13) . . . . ?
C8 O2 Cu1 O1 69.3(7) . . . . ?
C8 O2 Cu1 N1 7.71(15) . . . . ?
C8 O2 Cu1 O4 172.29(15) . . . . ?
C8 O2 Cu1 O5 -96.50(15) . . . . ?
C26 O21 Cu21 N21 -14.31(17) . . . . ?
C26 O21 Cu21 O22 67.8(4) . . . . ?
C26 O21 Cu21 O24 150.57(17) . . . . ?
C26 O21 Cu21 O25 -115.04(16) . . . . ?
C27 N21 Cu21 O21 9.99(18) . . . . ?
C29 N21 Cu21 O21 -172.98(13) . . . . ?
C27 N21 Cu21 O22 -159.12(18) . . . . ?
C29 N21 Cu21 O22 17.92(13) . . . . ?
C27 N21 Cu21 O24 -101.7(3) . . . . ?
C29 N21 Cu21 O24 75.3(3) . . . . ?
C27 N21 Cu21 O25 104.51(18) . . . . ?
C29 N21 Cu21 O25 -78.45(13) . . . . ?
C28 O22 Cu21 O21 -92.3(4) . . . . ?
C28 O22 Cu21 N21 -9.04(16) . . . . ?
C28 O22 Cu21 O24 -175.35(16) . . . . ?
C28 O22 Cu21 O25 90.56(16) . . . . ?

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
O4 H4A O21 0.944(4) 1.836(10) 2.7241(19) 155.7(18) 3_665
O4 H4B O22 0.955(4) 1.764(7) 2.6864(19) 161.3(11) 3_675
O5 H5A O3 0.827(5) 2.135(5) 2.805(2) 138.1(6) 3_775
O5 H5B O3 0.826(5) 2.080(6) 2.853(2) 155.7(10) 1_545
O24 H24A O2 0.834(5) 1.879(6) 2.7109(19) 175(2) 3_675
O24 H24B O1 0.830(5) 1.872(6) 2.6741(19) 162.1(14) 3_665
O25 H25A O23 0.838(5) 1.914(6) 2.750(2) 174.7(8) 1_545
O25 H25B O5 0.835(5) 2.060(7) 2.888(2) 171.0(14) 3_665

_diffrn_measured_fraction_theta_max 0.996
_diffrn_reflns_theta_full        26.37
_diffrn_measured_fraction_theta_full 0.996
_refine_diff_density_max         0.305
_refine_diff_density_min         -0.327
_refine_diff_density_rms         0.053

# Attachment '- 2_CCDC_784968.cif'

##############################################################################
### CIF submission form for molecular structure report (Acta Cryst. C) ###
### Version: 2.0.2 (6 July 1998) ###
##############################################################################

# This is an electronic "form" for submitting a structural paper to Acta Cryst.
# Section C as a Crystallographic Information File. Full details of the format
# of such files are given in the paper "The Crystallographic Information File
# (CIF): a New Standard Archive File for Crystallography" by S. R. Hall, F. H.
# Allen and I. D. Brown [Acta Cryst. (1991), A47, 655-685].
#
# The current version of the core CIF dictionary is obtainable from
# ftp://ftp.iucr.org/pub/cif_core.dic. The current version number is 2.0.1.
# A few data names below appear in the 1998 Notes for Authors [Acta Cryst.
# (1998), C54, 153-168] but are not yet in an approved dictionary; these
# are indicated by the comment 'Not in version 2.0.1'.
#
# Note that all fields should be numeric or character type EXCEPT those which
# are flagged as 'text' - free-form text of any length may be included in
# these latter fields provided the text block begins and ends with a semicolon
# as the first character of a new line. Note also that the query marks
# '?' are significant as placeholders, and should not be deleted where a data
# item is not given, UNLESS the accompanying data name is also deleted.
# Lines should not exceed 80 characters in length.
#
# An example file derived from this form and annotated in the 1998 Notes for
# Authors may be retrieved as ftp://ftp.iucr.org/pub/example.cif.

data_Ib
_database_code_depnum_ccdc_archive 'CCDC 784968'
#TrackingRef '- 2_CCDC_784968.cif'

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C11 H15 Cu N O6'
_chemical_formula_sum            'C11 H15 Cu N O6'
_chemical_formula_weight         320.78

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

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

_cell_length_a                   6.1624(2)
_cell_length_b                   25.7141(10)
_cell_length_c                   8.8937(4)
_cell_angle_alpha                90.00
_cell_angle_beta                 109.076(4)
_cell_angle_gamma                90.00
_cell_volume                     1331.91(9)
_cell_formula_units_Z            4
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    15521
_cell_measurement_theta_min      3.3883
_cell_measurement_theta_max      29.5443

_exptl_crystal_description       needle
_exptl_crystal_colour            'dark green'
_exptl_crystal_size_max          0.6920
_exptl_crystal_size_mid          0.2114
_exptl_crystal_size_min          0.0927
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.600
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             660
_exptl_absorpt_coefficient_mu    1.661
_exptl_absorpt_correction_type   analytical
_exptl_absorpt_process_details   
;
CrysAlis RED, Oxford Diffraction Ltd.,
Version 1.171.33.8 (release 02-06-2008 CrysAlis171 .NET)
(compiled Jun 3 2008,11:28:45)
Analytical numeric absorption correction using a multifaceted crystal
model based on expressions derived by R.C. Clark & J.S. Reid.
(Clark, R. C. & Reid, J. S. (1995). Acta Cryst. A51, 887-897)
;
_exptl_absorpt_correction_T_min  0.540
_exptl_absorpt_correction_T_max  0.871

_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  
;
Goniometer Xcalibur, detector: Ruby (Gemini Cu)
;
_diffrn_measurement_method       '\w scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         0
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  0
_diffrn_standards_decay_%        0
_diffrn_reflns_number            26634
_diffrn_reflns_av_R_equivalents  0.0485
_diffrn_reflns_av_sigmaI/netI    0.0272
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_k_min       -34
_diffrn_reflns_limit_k_max       35
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_theta_min         3.39
_diffrn_reflns_theta_max         29.60
_reflns_number_total             3497
_reflns_number_gt                2809
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'CrysAlis CCD (Oxford Diffraction, 2010)'
_computing_cell_refinement       'CrysAlis CCD'
_computing_data_reduction        'CrysAlis RED (Oxford Diffraction, 2010)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_molecular_graphics    'DIAMOND (Brandenburg, 1998)'
_computing_publication_material  'enCIFer (Allen et al., 2008)'

_refine_special_details          
;
Refinement of F^2^ against ALL reflections. The weighted R-factor wR and
goodness of fit S are based on F^2^, conventional R-factors R are based
on F, with F set to zero for negative F^2^. The threshold expression of
F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is
not relevant to the choice of reflections for refinement. R-factors based
on F^2^ are statistically about twice as large as those based on F, and R-
factors based on ALL data will be even larger.
Atoms C9, C10 and H10 are disordered with occupation factor 0.524 and 0.476.
;

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[\s^2^(Fo^2^)+(0.0588P)^2^+1.3013P] where P=(Fo^2^+2Fc^2^)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         3497
_refine_ls_number_parameters     224
_refine_ls_number_restraints     12
_refine_ls_R_factor_all          0.0572
_refine_ls_R_factor_gt           0.0453
_refine_ls_wR_factor_ref         0.1239
_refine_ls_wR_factor_gt          0.1204
_refine_ls_goodness_of_fit_ref   1.087
_refine_ls_restrained_S_all      1.085
_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
C1 C 0.7862(5) 0.16529(11) 0.6973(3) 0.0340(6) Uani 1 1 d . . .
C2 C 0.9331(6) 0.20111(13) 0.6591(4) 0.0441(7) Uani 1 1 d . . .
H2 H 0.9642 0.2327 0.7129 0.053 Uiso 1 1 calc R . .
C3 C 1.0318(6) 0.19060(14) 0.5441(4) 0.0512(8) Uani 1 1 d . . .
H3 H 1.1295 0.2145 0.5209 0.061 Uiso 1 1 calc R . .
C4 C 0.9824(6) 0.14332(14) 0.4631(4) 0.0502(8) Uani 1 1 d . . .
H4 H 1.0501 0.1354 0.3866 0.060 Uiso 1 1 calc R . .
C5 C 0.8355(6) 0.10841(13) 0.4949(4) 0.0453(7) Uani 1 1 d . . .
H5 H 0.8016 0.0777 0.4369 0.054 Uiso 1 1 calc R . .
C6 C 0.7345(5) 0.11781(11) 0.6129(3) 0.0337(6) Uani 1 1 d . A .
C7 C 0.7061(6) 0.17792(13) 0.8267(4) 0.0444(7) Uani 1 1 d . A .
H7A H 0.7515 0.2099 0.8756 0.053 Uiso 1 1 calc R . .
C8 C 0.2505(5) 0.10374(11) 1.0482(3) 0.0349(6) Uani 1 1 d . . .
C9A C 0.4364(16) 0.1458(3) 1.1069(10) 0.0409(18) Uani 0.524(11) 1 d P A 1
C9B C 0.3416(15) 0.1600(3) 1.0534(9) 0.0315(15) Uani 0.476(11) 1 d P A 2
C10A C 0.5933(10) 0.1578(2) 1.0551(7) 0.0365(18) Uani 0.524(11) 1 d P A 1
H10A H 0.663(13) 0.185(4) 1.097(9) 0.055 Uiso 0.524(11) 1 d P A 1
C10B C 0.4464(14) 0.1803(2) 0.9755(9) 0.043(2) Uani 0.476(11) 1 d P A 2
H10B H 0.576(17) 0.208(3) 1.039(12) 0.065 Uiso 0.476(11) 1 d P A 2
C11 C 0.3653(10) 0.18306(19) 1.2233(6) 0.0716(14) Uani 1 1 d D . .
H11A H 0.415(8) 0.1635(16) 1.320(3) 0.086 Uiso 1 1 d D . .
H11B H 0.409(8) 0.2183(7) 1.213(6) 0.086 Uiso 1 1 d D . .
H11C H 0.206(2) 0.1902(19) 1.204(6) 0.086 Uiso 1 1 d D . .
N1 N 0.5778(6) 0.14972(12) 0.8825(4) 0.0556(8) Uani 1 1 d . . .
O1 O 0.5995(4) 0.08245(8) 0.6403(3) 0.0406(5) Uani 1 1 d . . .
O2 O 0.2615(4) 0.07599(9) 0.9327(3) 0.0469(6) Uani 1 1 d . A .
O3 O 0.1285(4) 0.09231(9) 1.1289(3) 0.0470(5) Uani 1 1 d . A .
O4 O 0.2791(4) 0.02194(9) 0.6776(2) 0.0393(5) Uani 1 1 d D . .
H4A H 0.154(3) 0.0141(14) 0.690(3) 0.047 Uiso 1 1 d D . .
H4B H 0.277(5) 0.0219(14) 0.5826(13) 0.047 Uiso 1 1 d D . .
O5 O 0.7339(4) 0.03309(10) 0.9690(3) 0.0604(7) Uani 1 1 d D . .
H5A H 0.722(6) 0.0025(7) 0.998(5) 0.072 Uiso 1 1 d D . .
H5B H 0.867(3) 0.0456(13) 1.001(5) 0.072 Uiso 1 1 d D . .
O6 O 0.1636(4) 0.01126(9) 0.3522(3) 0.0405(5) Uani 1 1 d D . .
H6A H 0.246(5) -0.0149(7) 0.355(4) 0.049 Uiso 1 1 d D . .
H6B H 0.184(6) 0.0364(8) 0.298(4) 0.049 Uiso 1 1 d D . .
Cu1 Cu 0.45204(6) 0.082249(13) 0.79788(4) 0.03447(13) Uani 1 1 d . A .

loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_23
_atom_site_aniso_U_13
_atom_site_aniso_U_12
C1 0.0344(13) 0.0371(14) 0.0319(13) 0.0037(11) 0.0127(11) -0.0008(11)
C2 0.0475(17) 0.0432(17) 0.0428(16) 0.0040(13) 0.0166(14) -0.0098(13)
C3 0.0546(19) 0.059(2) 0.0498(18) 0.0085(15) 0.0299(16) -0.0106(16)
C4 0.0560(19) 0.060(2) 0.0477(18) 0.0075(15) 0.0347(16) 0.0007(16)
C5 0.0576(19) 0.0437(17) 0.0432(16) 0.0000(13) 0.0281(15) -0.0003(14)
C6 0.0340(13) 0.0385(14) 0.0320(13) 0.0054(11) 0.0153(11) 0.0000(11)
C7 0.0546(18) 0.0421(16) 0.0463(17) -0.0124(13) 0.0297(15) -0.0166(14)
C8 0.0346(14) 0.0386(14) 0.0340(14) -0.0016(11) 0.0146(11) -0.0034(11)
C9A 0.046(4) 0.046(4) 0.035(4) -0.012(3) 0.019(3) -0.014(3)
C9B 0.033(4) 0.033(3) 0.028(3) 0.004(2) 0.010(3) 0.006(3)
C10A 0.035(3) 0.047(4) 0.030(3) -0.012(2) 0.014(2) -0.011(3)
C10B 0.060(5) 0.030(3) 0.049(4) -0.011(3) 0.030(4) -0.007(3)
C11 0.101(3) 0.065(3) 0.075(3) -0.034(2) 0.065(3) -0.037(2)
N1 0.075(2) 0.0552(17) 0.0568(17) -0.0271(14) 0.0498(16) -0.0343(15)
O1 0.0516(12) 0.0395(11) 0.0413(11) -0.0083(8) 0.0296(10) -0.0109(9)
O2 0.0556(13) 0.0468(13) 0.0520(13) -0.0145(10) 0.0365(11) -0.0187(10)
O3 0.0538(13) 0.0518(13) 0.0464(12) -0.0051(10) 0.0313(11) -0.0131(10)
O4 0.0402(11) 0.0485(12) 0.0328(10) -0.0095(9) 0.0166(9) -0.0149(9)
O5 0.0456(13) 0.0543(15) 0.0657(16) 0.0168(13) -0.0029(12) -0.0126(11)
O6 0.0464(12) 0.0428(12) 0.0380(11) -0.0027(9) 0.0218(10) -0.0043(9)
Cu1 0.0383(2) 0.0366(2) 0.0339(2) -0.00691(13) 0.01905(15) -0.00997(13)

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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
C1 C2 1.409(4) . ?
C1 C6 1.414(4) . ?
C1 C7 1.430(4) . ?
C2 C3 1.376(5) . ?
C2 H2 0.9300 . ?
C3 C4 1.395(5) . ?
C3 H3 0.9300 . ?
C4 C5 1.368(5) . ?
C4 H4 0.9300 . ?
C5 C6 1.405(4) . ?
C5 H5 0.9300 . ?
C6 O1 1.308(3) . ?
C7 N1 1.286(4) . ?
C7 H7A 0.9300 . ?
C8 O3 1.233(3) . ?
C8 O2 1.271(4) . ?
C8 C9A 1.537(7) . ?
C8 C9B 1.547(7) . ?
C9A C10A 1.238(9) . ?
C9A C11 1.575(8) . ?
C9B C10B 1.210(9) . ?
C9B C11 1.585(8) . ?
C10A N1 1.521(6) . ?
C10A H10A 0.84(9) . ?
C10A H10B 1.30(9) . ?
C10B N1 1.548(7) . ?
C10B H10A 1.42(8) . ?
C10B H10B 1.08(10) . ?
C11 H11A 0.958(5) . ?
C11 H11B 0.959(5) . ?
C11 H11C 0.960(5) . ?
N1 Cu1 1.948(3) . ?
O1 Cu1 1.903(2) . ?
O2 Cu1 1.940(2) . ?
O4 Cu1 1.985(2) . ?
O4 H4A 0.840(5) . ?
O4 H4B 0.840(5) . ?
O5 Cu1 2.281(2) . ?
O5 H5A 0.839(5) . ?
O5 H5B 0.839(5) . ?
O6 H6A 0.840(5) . ?
O6 H6B 0.838(5) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C2 C1 C6 119.2(3) . . ?
C2 C1 C7 117.7(3) . . ?
C6 C1 C7 123.1(3) . . ?
C3 C2 C1 121.7(3) . . ?
C3 C2 H2 119.1 . . ?
C1 C2 H2 119.1 . . ?
C2 C3 C4 118.7(3) . . ?
C2 C3 H3 120.7 . . ?
C4 C3 H3 120.7 . . ?
C5 C4 C3 120.8(3) . . ?
C5 C4 H4 119.6 . . ?
C3 C4 H4 119.6 . . ?
C4 C5 C6 121.7(3) . . ?
C4 C5 H5 119.1 . . ?
C6 C5 H5 119.1 . . ?
O1 C6 C5 118.9(3) . . ?
O1 C6 C1 123.2(3) . . ?
C5 C6 C1 117.9(3) . . ?
N1 C7 C1 126.9(3) . . ?
N1 C7 H7A 116.6 . . ?
C1 C7 H7A 116.6 . . ?
O3 C8 O2 122.7(3) . . ?
O3 C8 C9A 119.9(3) . . ?
O2 C8 C9A 116.0(3) . . ?
O3 C8 C9B 119.3(3) . . ?
O2 C8 C9B 115.8(3) . . ?
C9A C8 C9B 27.0(3) . . ?
C10A C9A C8 129.4(6) . . ?
C10A C9A C11 120.8(5) . . ?
C8 C9A C11 108.4(5) . . ?
C10B C9B C8 130.0(6) . . ?
C10B C9B C11 119.0(6) . . ?
C8 C9B C11 107.4(5) . . ?
C9A C10A N1 122.9(6) . . ?
C9A C10A H10A 113(5) . . ?
N1 C10A H10A 114(5) . . ?
C9A C10A H10B 104(4) . . ?
N1 C10A H10B 93(4) . . ?
H10A C10A H10B 40(6) . . ?
C9B C10B N1 123.9(6) . . ?
C9B C10B H10A 98(3) . . ?
N1 C10B H10A 86(3) . . ?
C9B C10B H10B 115(5) . . ?
N1 C10B H10B 101(5) . . ?
H10A C10B H10B 37(5) . . ?
C9A C11 C9B 26.4(3) . . ?
C9A C11 H11A 101(3) . . ?
C9B C11 H11A 124(3) . . ?
C9A C11 H11B 111(3) . . ?
C9B C11 H11B 101(3) . . ?
H11A C11 H11B 125(4) . . ?
C9A C11 H11C 119(3) . . ?
C9B C11 H11C 98(3) . . ?
H11A C11 H11C 105(4) . . ?
H11B C11 H11C 96(4) . . ?
C7 N1 C10A 118.0(3) . . ?
C7 N1 C10B 114.5(4) . . ?
C10A N1 C10B 42.5(4) . . ?
C7 N1 Cu1 124.8(2) . . ?
C10A N1 Cu1 113.4(3) . . ?
C10B N1 Cu1 116.6(3) . . ?
C6 O1 Cu1 128.66(18) . . ?
C8 O2 Cu1 131.00(19) . . ?
Cu1 O4 H4A 118(2) . . ?
Cu1 O4 H4B 112(2) . . ?
H4A O4 H4B 115.1(10) . . ?
Cu1 O5 H5A 127(2) . . ?
Cu1 O5 H5B 117(2) . . ?
H5A O5 H5B 115.5(10) . . ?
H6A O6 H6B 115.5(10) . . ?
O1 Cu1 O2 170.59(9) . . ?
O1 Cu1 N1 93.24(10) . . ?
O2 Cu1 N1 94.59(10) . . ?
O1 Cu1 O4 84.64(9) . . ?
O2 Cu1 O4 86.64(9) . . ?
N1 Cu1 O4 168.41(13) . . ?
O1 Cu1 O5 92.86(11) . . ?
O2 Cu1 O5 91.41(11) . . ?
N1 Cu1 O5 96.65(13) . . ?
O4 Cu1 O5 94.84(9) . . ?

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
C6 C1 C2 C3 -1.5(5) . . . . ?
C7 C1 C2 C3 175.3(3) . . . . ?
C1 C2 C3 C4 0.6(5) . . . . ?
C2 C3 C4 C5 1.2(5) . . . . ?
C3 C4 C5 C6 -2.0(5) . . . . ?
C4 C5 C6 O1 -178.5(3) . . . . ?
C4 C5 C6 C1 1.0(5) . . . . ?
C2 C1 C6 O1 -179.8(3) . . . . ?
C7 C1 C6 O1 3.6(5) . . . . ?
C2 C1 C6 C5 0.7(4) . . . . ?
C7 C1 C6 C5 -175.9(3) . . . . ?
C2 C1 C7 N1 -177.6(4) . . . . ?
C6 C1 C7 N1 -1.0(6) . . . . ?
O3 C8 C9A C10A 169.5(9) . . . . ?
O2 C8 C9A C10A 2.3(13) . . . . ?
C9B C8 C9A C10A -93.9(13) . . . . ?
O3 C8 C9A C11 -24.6(9) . . . . ?
O2 C8 C9A C11 168.3(5) . . . . ?
C9B C8 C9A C11 72.1(10) . . . . ?
O3 C8 C9B C10B -173.4(8) . . . . ?
O2 C8 C9B C10B -9.6(11) . . . . ?
C9A C8 C9B C10B 87.6(12) . . . . ?
O3 C8 C9B C11 28.9(7) . . . . ?
O2 C8 C9B C11 -167.3(4) . . . . ?
C9A C8 C9B C11 -70.1(9) . . . . ?
C8 C9A C10A N1 27.3(14) . . . . ?
C11 C9A C10A N1 -137.2(8) . . . . ?
C8 C9B C10B N1 -18.9(13) . . . . ?
C11 C9B C10B N1 136.7(7) . . . . ?
C10A C9A C11 C9B 95.5(13) . . . . ?
C8 C9A C11 C9B -71.9(9) . . . . ?
C10B C9B C11 C9A -90.8(12) . . . . ?
C8 C9B C11 C9A 69.9(8) . . . . ?
C1 C7 N1 C10A 154.4(4) . . . . ?
C1 C7 N1 C10B -158.0(4) . . . . ?
C1 C7 N1 Cu1 -1.9(6) . . . . ?
C9A C10A N1 C7 157.0(7) . . . . ?
C9A C10A N1 C10B 60.4(8) . . . . ?
C9A C10A N1 Cu1 -44.1(8) . . . . ?
C9B C10B N1 C7 -170.1(7) . . . . ?
C9B C10B N1 C10A -64.7(8) . . . . ?
C9B C10B N1 Cu1 31.7(9) . . . . ?
C5 C6 O1 Cu1 176.4(2) . . . . ?
C1 C6 O1 Cu1 -3.1(4) . . . . ?
O3 C8 O2 Cu1 -175.1(2) . . . . ?
C9A C8 O2 Cu1 -8.4(6) . . . . ?
C9B C8 O2 Cu1 21.7(5) . . . . ?
C6 O1 Cu1 O2 146.8(6) . . . . ?
C6 O1 Cu1 N1 0.5(3) . . . . ?
C6 O1 Cu1 O4 169.0(3) . . . . ?
C6 O1 Cu1 O5 -96.4(3) . . . . ?
C8 O2 Cu1 O1 -154.1(5) . . . . ?
C8 O2 Cu1 N1 -7.9(3) . . . . ?
C8 O2 Cu1 O4 -176.3(3) . . . . ?
C8 O2 Cu1 O5 88.9(3) . . . . ?
C7 N1 Cu1 O1 1.9(4) . . . . ?
C10A N1 Cu1 O1 -155.3(3) . . . . ?
C10B N1 Cu1 O1 157.7(4) . . . . ?
C7 N1 Cu1 O2 -172.8(3) . . . . ?
C10A N1 Cu1 O2 29.9(3) . . . . ?
C10B N1 Cu1 O2 -17.1(4) . . . . ?
C7 N1 Cu1 O4 -77.2(7) . . . . ?
C10A N1 Cu1 O4 125.6(5) . . . . ?
C10B N1 Cu1 O4 78.6(6) . . . . ?
C7 N1 Cu1 O5 95.2(4) . . . . ?
C10A N1 Cu1 O5 -62.1(3) . . . . ?
C10B N1 Cu1 O5 -109.1(4) . . . . ?

_diffrn_measured_fraction_theta_max 0.930
_diffrn_reflns_theta_full        25.00
_diffrn_measured_fraction_theta_full 0.998
_refine_diff_density_max         0.524
_refine_diff_density_min         -0.556
_refine_diff_density_rms         0.077

# Attachment '- 3_CCDC784969.cif'

##############################################################################
### CIF submission form for molecular structure report (Acta Cryst. C) ###
### Version: 2.0.2 (6 July 1998) ###
##############################################################################

# This is an electronic "form" for submitting a structural paper to Acta Cryst.
# Section C as a Crystallographic Information File. Full details of the format
# of such files are given in the paper "The Crystallographic Information File
# (CIF): a New Standard Archive File for Crystallography" by S. R. Hall, F. H.
# Allen and I. D. Brown [Acta Cryst. (1991), A47, 655-685].
#
# The current version of the core CIF dictionary is obtainable from
# ftp://ftp.iucr.org/pub/cif_core.dic. The current version number is 2.0.1.
# A few data names below appear in the 1998 Notes for Authors [Acta Cryst.
# (1998), C54, 153-168] but are not yet in an approved dictionary; these
# are indicated by the comment 'Not in version 2.0.1'.
#
# Note that all fields should be numeric or character type EXCEPT those which
# are flagged as 'text' - free-form text of any length may be included in
# these latter fields provided the text block begins and ends with a semicolon
# as the first character of a new line. Note also that the query marks
# '?' are significant as placeholders, and should not be deleted where a data
# item is not given, UNLESS the accompanying data name is also deleted.
# Lines should not exceed 80 characters in length.
#
# An example file derived from this form and annotated in the 1998 Notes for
# Authors may be retrieved as ftp://ftp.iucr.org/pub/example.cif.

#==============================================================================
data_III
_database_code_depnum_ccdc_archive 'CCDC 784969'
#TrackingRef '- 3_CCDC784969.cif'

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C11 H13 Cu N O4'
_chemical_formula_sum            'C11 H13 Cu N O4'
_chemical_formula_weight         286.76

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

_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_H-M   'P 21/n '
_symmetry_space_group_name_Hall  '-P 2yn '

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

_cell_length_a                   8.0368(3)
_cell_length_b                   5.4782(2)
_cell_length_c                   25.5765(9)
_cell_angle_alpha                90.00
_cell_angle_beta                 91.251(3)
_cell_angle_gamma                90.00
_cell_volume                     1125.79(7)
_cell_formula_units_Z            4
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    7427
_cell_measurement_theta_min      3.4411
_cell_measurement_theta_max      29.3917

_exptl_crystal_description       needle
_exptl_crystal_colour            'dark green'
_exptl_crystal_size_max          0.4562
_exptl_crystal_size_mid          0.0445
_exptl_crystal_size_min          0.0166
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.692
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             588
_exptl_absorpt_coefficient_mu    1.941
_exptl_absorpt_correction_type   analytical
_exptl_absorpt_process_details   
;
CrysAlisPro, Oxford Diffraction Ltd.,
Version 1.171.33.62 (release 16-03-2010 CrysAlis171 .NET)
(compiled Mar 16 2010,16:26:05)
Analytical numeric absorption correction using a multifaceted crystal
model based on expressions derived by R.C. Clark & J.S. Reid.
(Clark, R. C. & Reid, J. S. (1995). Acta Cryst. A51, 887-897)
;

_exptl_absorpt_correction_T_min  0.681
_exptl_absorpt_correction_T_max  0.969

_exptl_special_details           
;
?
;

_diffrn_ambient_temperature      293(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'Enhance (Mo) X-ray Source'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Oxford Diffraction Gemini R CCD '
_diffrn_measurement_method       
;
Rotation method data acquisition using \w and \f scans
;
_diffrn_detector_area_resol_mean 10.4340
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            20145
_diffrn_reflns_av_R_equivalents  0.0813
_diffrn_reflns_av_sigmaI/netI    0.0518
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       -6
_diffrn_reflns_limit_k_max       6
_diffrn_reflns_limit_l_min       -31
_diffrn_reflns_limit_l_max       31
_diffrn_reflns_theta_min         4.42
_diffrn_reflns_theta_max         26.37
_reflns_number_total             2279
_reflns_number_gt                1685
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'CrysAlis CCD (Oxford Diffraction, 2010)'
_computing_cell_refinement       'CrysAlis CCD'
_computing_data_reduction        'CrysAlis RED (Oxford Diffraction, 2010)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_molecular_graphics    'DIAMOND (Brandenburg, 1998)'
_computing_publication_material  ' enCIFer (Allen et al., 2008)'

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

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[\s^2^(Fo^2^)+(0.0715P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         2279
_refine_ls_number_parameters     228
_refine_ls_number_restraints     402
_refine_ls_R_factor_all          0.0667
_refine_ls_R_factor_gt           0.0472
_refine_ls_wR_factor_ref         0.1215
_refine_ls_wR_factor_gt          0.1167
_refine_ls_goodness_of_fit_ref   1.049
_refine_ls_restrained_S_all      0.980
_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
C1 C 1.087(2) 0.862(2) 0.0757(8) 0.035(3) Uani 0.494(7) 1 d PU A 1
C2 C 1.1419(6) 0.8973(9) 0.0236(2) 0.048(2) Uani 0.494(7) 1 d PU A 1
H2 H 1.0834 0.8219 -0.0037 0.057 Uiso 0.494(7) 1 calc PR A 1
C3 C 1.2751(6) 1.0351(9) 0.0123(2) 0.048(2) Uani 0.494(7) 1 d PRU A 1
H3 H 1.3107 1.0519 -0.0219 0.057 Uiso 0.494(7) 1 d PR A 1
C4 C 1.3585(6) 1.1532(9) 0.0543(2) 0.053(3) Uani 0.494(7) 1 d PRU A 1
H4 H 1.4503 1.2508 0.0477 0.064 Uiso 0.494(7) 1 d PR A 1
C5 C 1.3072(6) 1.1272(9) 0.1047(2) 0.052(2) Uani 0.494(7) 1 d PRU A 1
H5 H 1.3713 1.1931 0.1319 0.062 Uiso 0.494(7) 1 d PR A 1
C6 C 1.1599(6) 1.0030(9) 0.1159(2) 0.047(3) Uani 0.494(7) 1 d PRU A 1
C7 C 0.9419(12) 0.7063(19) 0.0816(3) 0.041(2) Uani 0.507(10) 1 d PU A 1
H7 H 0.8794 0.6688 0.0517 0.050 Uiso 0.507(10) 1 calc PR A 1
C8 C 0.7210(14) 0.502(2) 0.1195(4) 0.047(2) Uani 0.507(10) 1 d PU A 1
H8B H 0.7129 0.3640 0.1430 0.057 Uiso 0.507(10) 1 calc PR A 1
H8A H 0.7165 0.4371 0.0842 0.057 Uiso 0.507(10) 1 calc PR A 1
C9 C 0.5658(11) 0.655(2) 0.1262(4) 0.051(3) Uani 0.507(10) 1 d PU A 1
H9B H 0.4691 0.5502 0.1225 0.061 Uiso 0.507(10) 1 calc PR A 1
H9A H 0.5597 0.7753 0.0984 0.061 Uiso 0.507(10) 1 calc PR A 1
C10 C 0.5581(13) 0.7878(19) 0.1788(4) 0.043(2) Uani 0.507(10) 1 d PU A 1
H10B H 0.4453 0.8405 0.1856 0.052 Uiso 0.507(10) 1 calc PR A 1
H10A H 0.6306 0.9293 0.1793 0.052 Uiso 0.507(10) 1 calc PR A 1
C11 C 0.6173(5) 0.5975(7) 0.21975(16) 0.0410(9) Uani 1 1 d U . .
C21 C 1.114(2) 0.786(2) 0.0780(8) 0.040(3) Uani 0.506(7) 1 d PU A 2
C22 C 1.1986(6) 0.7757(10) 0.0318(2) 0.047(2) Uani 0.506(7) 1 d PU A 2
H22 H 1.1913 0.6334 0.0120 0.056 Uiso 0.506(7) 1 calc PR A 2
C23 C 1.2902(6) 0.9583(10) 0.0139(2) 0.058(3) Uani 0.506(7) 1 d PRU A 2
H23 H 1.3496 0.9415 -0.0167 0.070 Uiso 0.506(7) 1 d PR A 2
C24 C 1.2947(6) 1.1762(10) 0.0422(2) 0.053(3) Uani 0.506(7) 1 d PRU A 2
H24 H 1.3502 1.3104 0.0288 0.063 Uiso 0.506(7) 1 d PR A 2
C25 C 1.2186(6) 1.1957(10) 0.0896(2) 0.047(2) Uani 0.506(7) 1 d PRU A 2
H25 H 1.2207 1.3415 0.1083 0.056 Uiso 0.506(7) 1 d PR A 2
C26 C 1.1349(6) 0.9813(10) 0.1098(2) 0.043(3) Uani 0.506(7) 1 d PRU A 2
C27 C 1.0041(12) 0.5900(18) 0.0908(3) 0.040(2) Uani 0.493(10) 1 d PU A 2
H27 H 1.0117 0.4435 0.0726 0.048 Uiso 0.493(10) 1 calc PR A 2
C28 C 0.7911(12) 0.3682(18) 0.1316(4) 0.044(2) Uani 0.493(10) 1 d PU A 2
H28B H 0.8210 0.2541 0.1043 0.053 Uiso 0.493(10) 1 calc PR A 2
H28A H 0.8061 0.2912 0.1655 0.053 Uiso 0.493(10) 1 calc PR A 2
C29 C 0.6125(14) 0.466(2) 0.1233(4) 0.054(3) Uani 0.493(10) 1 d PU A 2
H29B H 0.6012 0.5339 0.0884 0.064 Uiso 0.493(10) 1 calc PR A 2
H29A H 0.5347 0.3309 0.1258 0.064 Uiso 0.493(10) 1 calc PR A 2
C30 C 0.5676(12) 0.660(2) 0.1632(5) 0.049(3) Uani 0.493(10) 1 d PU A 2
H30B H 0.4483 0.6874 0.1613 0.059 Uiso 0.493(10) 1 calc PR A 2
H30A H 0.6214 0.8122 0.1538 0.059 Uiso 0.493(10) 1 calc PR A 2
N1 N 0.8913(5) 0.6111(8) 0.12788(15) 0.0696(12) Uani 1 1 d U . .
O1 O 1.0851(5) 1.0029(6) 0.16015(13) 0.0787(11) Uani 1 1 d U . .
O2 O 0.7685(3) 0.6019(4) 0.23228(10) 0.0379(6) Uani 1 1 d U A .
O3 O 0.9909(3) 0.9785(4) 0.25608(10) 0.0418(6) Uani 1 1 d U . .
O5 O 1.1456(4) 0.4786(5) 0.21428(15) 0.0632(9) Uani 1 1 d DU . .
HWA H 1.2468(16) 0.497(7) 0.222(2) 0.076 Uiso 1 1 d D . .
HWB H 1.120(5) 0.344(4) 0.2010(19) 0.076 Uiso 1 1 d D . .
Cu1 Cu 0.94234(5) 0.77833(7) 0.194032(18) 0.03492(19) Uani 1 1 d U A .

loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_23
_atom_site_aniso_U_13
_atom_site_aniso_U_12
C1 0.032(6) 0.029(6) 0.045(5) 0.001(5) 0.008(4) 0.006(5)
C2 0.041(5) 0.054(5) 0.048(5) -0.004(4) 0.005(4) -0.001(4)
C3 0.046(6) 0.047(5) 0.051(5) 0.000(4) 0.019(4) 0.000(4)
C4 0.034(6) 0.051(5) 0.075(6) 0.006(4) 0.013(5) -0.008(4)
C5 0.052(5) 0.044(5) 0.060(5) -0.001(4) 0.007(4) -0.008(4)
C6 0.055(6) 0.033(5) 0.052(5) -0.014(5) 0.013(4) -0.011(5)
C7 0.044(5) 0.037(5) 0.043(4) -0.006(4) -0.004(3) 0.002(4)
C8 0.048(5) 0.053(6) 0.041(5) -0.010(4) -0.001(4) -0.020(4)
C9 0.041(4) 0.061(6) 0.052(5) 0.005(5) -0.005(4) -0.018(4)
C10 0.045(5) 0.039(5) 0.047(5) 0.010(4) -0.004(4) -0.002(4)
C11 0.031(2) 0.040(2) 0.052(2) 0.0108(17) 0.0034(18) 0.0055(17)
C21 0.035(6) 0.040(6) 0.045(5) -0.006(6) 0.001(4) 0.002(5)
C22 0.038(5) 0.062(5) 0.040(4) -0.004(4) -0.004(3) -0.001(4)
C23 0.033(6) 0.083(6) 0.060(6) 0.001(4) 0.007(4) -0.005(4)
C24 0.037(6) 0.061(5) 0.061(6) 0.023(4) 0.005(5) -0.003(4)
C25 0.042(5) 0.042(4) 0.057(5) 0.006(4) -0.002(4) -0.011(4)
C26 0.041(5) 0.040(5) 0.048(5) 0.001(4) 0.006(4) -0.018(5)
C27 0.050(5) 0.026(4) 0.042(5) -0.003(3) -0.007(3) 0.002(4)
C28 0.048(5) 0.035(5) 0.048(5) -0.007(4) -0.007(4) -0.015(4)
C29 0.040(5) 0.067(7) 0.052(5) 0.011(4) -0.019(4) -0.018(5)
C30 0.029(5) 0.052(6) 0.065(7) 0.021(6) -0.003(5) -0.005(4)
N1 0.060(2) 0.098(3) 0.051(2) -0.027(2) 0.0131(18) -0.052(2)
O1 0.120(3) 0.0541(18) 0.064(2) -0.0180(15) 0.039(2) -0.0539(19)
O2 0.0339(14) 0.0311(13) 0.0488(16) 0.0061(11) 0.0003(11) -0.0063(11)
O3 0.0291(14) 0.0446(14) 0.0517(17) -0.0135(12) 0.0032(12) -0.0019(11)
O5 0.0511(18) 0.0372(15) 0.101(3) -0.0074(16) -0.0124(17) 0.0018(14)
Cu1 0.0348(3) 0.0273(3) 0.0427(3) -0.00230(19) 0.00121(19) -0.00682(18)

_geom_special_details            
;
All esds (except the esd in the dihedral angle between two l.s. planes)
are estimated using the full covariance matrix. The cell esds are taken
into account individually in the estimation of esds in distances, angles
and torsion angles; correlations between esds in cell parameters are only
used when they are defined by crystal symmetry. An approximate (isotropic)
treatment of cell esds is used for estimating esds involving l.s. planes.
Non-hydrogen atoms C1, C2, C3, C4, C5, C6 and C21, C22, C23, C24, C25, C26
are disordered with occupation factor 0.495 and 0.505, as well as atoms
C8, C8, C10 and C28, C28, C30 with occupation factor 0.508 and 0.492.
;

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
C1 C6 1.405(18) . ?
C1 C2 1.427(19) . ?
C1 C7 1.453(19) . ?
C2 C3 1.3466 . ?
C2 H2 0.9300 . ?
C3 C4 1.4122 . ?
C3 H3 0.9300 . ?
C3 H23 1.0910 . ?
C4 C5 1.3674 . ?
C4 H4 0.9300 . ?
C4 H24 1.0821 . ?
C5 C6 1.4010 . ?
C5 H5 0.9300 . ?
C5 H25 1.3688 . ?
C6 O1 1.292(6) . ?
C7 N1 1.363(10) . ?
C7 H7 0.9300 . ?
C8 N1 1.504(11) . ?
C8 C9 1.516(15) . ?
C8 H8B 0.9700 . ?
C8 H8A 0.9700 . ?
C9 C10 1.531(14) . ?
C9 H9B 0.9700 . ?
C9 H9A 0.9700 . ?
C10 C11 1.545(10) . ?
C10 H10B 0.9700 . ?
C10 H10A 0.9700 . ?
C11 O2 1.251(4) . ?
C11 O3 1.260(4) 2_645 ?
C11 C30 1.531(13) . ?
C21 C26 1.354(16) . ?
C21 C22 1.38(2) . ?
C21 C27 1.431(18) . ?
C22 C23 1.3296 . ?
C22 H22 0.9300 . ?
C23 C24 1.3966 . ?
C23 H3 1.0649 . ?
C23 H23 0.9300 . ?
C24 C25 1.3737 . ?
C24 H4 1.3201 . ?
C24 H24 0.9300 . ?
C25 C26 1.4532 . ?
C25 H25 0.9300 . ?
C26 O1 1.363(7) . ?
C27 N1 1.332(10) . ?
C27 H27 0.9300 . ?
C28 C29 1.541(14) . ?
C28 N1 1.559(9) . ?
C28 H28B 0.9700 . ?
C28 H28A 0.9700 . ?
C29 C30 1.525(17) . ?
C29 H29B 0.9700 . ?
C29 H29A 0.9700 . ?
C30 H30B 0.9700 . ?
C30 H30A 0.9700 . ?
N1 Cu1 1.960(3) . ?
O1 Cu1 1.904(3) . ?
O2 Cu1 1.975(2) . ?
O3 C11 1.260(4) 2_655 ?
O3 Cu1 1.961(2) . ?
O5 Cu1 2.365(3) . ?
O5 HWA 0.840(5) . ?
O5 HWB 0.838(5) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C6 C1 C2 118.4(12) . . ?
C6 C1 C7 124.8(14) . . ?
C2 C1 C7 116.3(13) . . ?
C3 C2 C1 122.8(7) . . ?
C3 C2 H2 118.6 . . ?
C1 C2 H2 118.6 . . ?
C2 C3 C4 117.3 . . ?
C2 C3 H3 121.3 . . ?
C4 C3 H3 121.3 . . ?
C2 C3 H23 109.5 . . ?
C4 C3 H23 118.3 . . ?
H3 C3 H23 39.0 . . ?
C5 C4 C3 121.4 . . ?
C5 C4 H4 119.3 . . ?
C3 C4 H4 119.3 . . ?
C5 C4 H24 129.4 . . ?
C3 C4 H24 83.3 . . ?
H4 C4 H24 58.0 . . ?
C4 C5 C6 121.2 . . ?
C4 C5 H5 119.4 . . ?
C6 C5 H5 119.4 . . ?
C4 C5 H25 97.9 . . ?
C6 C5 H25 88.2 . . ?
H5 C5 H25 83.7 . . ?
O1 C6 C5 126.2(3) . . ?
O1 C6 C1 116.4(8) . . ?
C5 C6 C1 117.3(7) . . ?
N1 C7 C1 124.7(10) . . ?
N1 C7 H7 117.6 . . ?
C1 C7 H7 117.6 . . ?
N1 C8 C9 120.8(7) . . ?
N1 C8 H8B 107.1 . . ?
C9 C8 H8B 107.1 . . ?
N1 C8 H8A 107.1 . . ?
C9 C8 H8A 107.1 . . ?
H8B C8 H8A 106.8 . . ?
C8 C9 C10 114.3(8) . . ?
C8 C9 H9B 108.7 . . ?
C10 C9 H9B 108.7 . . ?
C8 C9 H9A 108.7 . . ?
C10 C9 H9A 108.7 . . ?
H9B C9 H9A 107.6 . . ?
C9 C10 C11 104.9(7) . . ?
C9 C10 H10B 110.8 . . ?
C11 C10 H10B 110.8 . . ?
C9 C10 H10A 110.8 . . ?
C11 C10 H10A 110.8 . . ?
H10B C10 H10A 108.8 . . ?
O2 C11 O3 124.2(3) . 2_645 ?
O2 C11 C30 118.0(5) . . ?
O3 C11 C30 114.3(5) 2_645 . ?
O2 C11 C10 116.4(5) . . ?
O3 C11 C10 118.4(5) 2_645 . ?
C30 C11 C10 30.4(4) . . ?
C26 C21 C22 119.3(12) . . ?
C26 C21 C27 121.7(14) . . ?
C22 C21 C27 119.0(12) . . ?
C23 C22 C21 123.6(6) . . ?
C23 C22 H22 118.2 . . ?
C21 C22 H22 118.2 . . ?
C22 C23 C24 118.2 . . ?
C22 C23 H3 139.1 . . ?
C24 C23 H3 91.9 . . ?
C22 C23 H23 120.9 . . ?
C24 C23 H23 120.9 . . ?
H3 C23 H23 39.9 . . ?
C25 C24 C23 121.2 . . ?
C25 C24 H4 108.8 . . ?
C23 C24 H4 109.5 . . ?
C25 C24 H24 119.4 . . ?
C23 C24 H24 119.4 . . ?
H4 C24 H24 48.2 . . ?
C24 C25 C26 117.9 . . ?
C24 C25 H25 121.0 . . ?
C26 C25 H25 121.0 . . ?
C21 C26 O1 127.0(9) . . ?
C21 C26 C25 118.7(8) . . ?
O1 C26 C25 114.4(2) . . ?
N1 C27 C21 122.1(10) . . ?
N1 C27 H27 119.0 . . ?
C21 C27 H27 119.0 . . ?
C29 C28 N1 100.2(7) . . ?
C29 C28 H28B 111.7 . . ?
N1 C28 H28B 111.7 . . ?
C29 C28 H28A 111.7 . . ?
N1 C28 H28A 111.7 . . ?
H28B C28 H28A 109.5 . . ?
C30 C29 C28 112.6(8) . . ?
C30 C29 H29B 109.1 . . ?
C28 C29 H29B 109.1 . . ?
C30 C29 H29A 109.1 . . ?
C28 C29 H29A 109.1 . . ?
H29B C29 H29A 107.8 . . ?
C29 C30 C11 114.4(8) . . ?
C29 C30 H30B 108.7 . . ?
C11 C30 H30B 108.7 . . ?
C29 C30 H30A 108.7 . . ?
C11 C30 H30A 108.7 . . ?
H30B C30 H30A 107.6 . . ?
C27 N1 C7 36.3(4) . . ?
C27 N1 C8 119.7(5) . . ?
C7 N1 C8 108.4(6) . . ?
C27 N1 C28 109.2(6) . . ?
C7 N1 C28 122.9(5) . . ?
C8 N1 C28 36.9(4) . . ?
C27 N1 Cu1 121.5(4) . . ?
C7 N1 Cu1 120.6(4) . . ?
C8 N1 Cu1 118.8(4) . . ?
C28 N1 Cu1 116.5(4) . . ?
C6 O1 C26 11.7(3) . . ?
C6 O1 Cu1 134.0(3) . . ?
C26 O1 Cu1 124.5(3) . . ?
C11 O2 Cu1 125.2(2) . . ?
C11 O3 Cu1 124.0(2) 2_655 . ?
Cu1 O5 HWA 129(3) . . ?
Cu1 O5 HWB 111(3) . . ?
HWA O5 HWB 115.6(10) . . ?
O1 Cu1 N1 91.49(15) . . ?
O1 Cu1 O3 84.02(12) . . ?
N1 Cu1 O3 173.88(16) . . ?
O1 Cu1 O2 168.92(13) . . ?
N1 Cu1 O2 93.54(13) . . ?
O3 Cu1 O2 90.18(10) . . ?
O1 Cu1 O5 97.35(16) . . ?
N1 Cu1 O5 89.72(17) . . ?
O3 Cu1 O5 94.97(11) . . ?
O2 Cu1 O5 92.54(11) . . ?

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
C6 C1 C2 C3 8.9(13) . . . . ?
C7 C1 C2 C3 -179.4(7) . . . . ?
C1 C2 C3 C4 -1.8(6) . . . . ?
C2 C3 C4 C5 0.6 . . . . ?
C3 C4 C5 C6 -6.7 . . . . ?
C4 C5 C6 O1 -167.4(3) . . . . ?
C4 C5 C6 C1 13.5(6) . . . . ?
C2 C1 C6 O1 166.5(7) . . . . ?
C7 C1 C6 O1 -4.4(15) . . . . ?
C2 C1 C6 C5 -14.3(12) . . . . ?
C7 C1 C6 C5 174.8(9) . . . . ?
C6 C1 C7 N1 -22.9(18) . . . . ?
C2 C1 C7 N1 166.0(9) . . . . ?
N1 C8 C9 C10 -53.1(12) . . . . ?
C8 C9 C10 C11 -43.0(10) . . . . ?
C9 C10 C11 O2 94.1(7) . . . . ?
C9 C10 C11 O3 -97.1(7) . . . 2_645 ?
C9 C10 C11 C30 -6.9(9) . . . . ?
C26 C21 C22 C23 -6.1(16) . . . . ?
C27 C21 C22 C23 173.0(8) . . . . ?
C21 C22 C23 C24 -3.0(8) . . . . ?
C22 C23 C24 C25 5.5 . . . . ?
C23 C24 C25 C26 0.8 . . . . ?
C22 C21 C26 O1 -167.8(7) . . . . ?
C27 C21 C26 O1 13.2(18) . . . . ?
C22 C21 C26 C25 12.2(15) . . . . ?
C27 C21 C26 C25 -166.8(10) . . . . ?
C24 C25 C26 C21 -9.7(8) . . . . ?
C24 C25 C26 O1 170.3(3) . . . . ?
C26 C21 C27 N1 15(2) . . . . ?
C22 C21 C27 N1 -164.4(9) . . . . ?
N1 C28 C29 C30 -57.0(9) . . . . ?
C28 C29 C30 C11 -45.6(11) . . . . ?
O2 C11 C30 C29 71.7(9) . . . . ?
O3 C11 C30 C29 -88.0(8) 2_645 . . . ?
C10 C11 C30 C29 166.7(16) . . . . ?
C21 C27 N1 C7 59.5(12) . . . . ?
C21 C27 N1 C8 140.2(11) . . . . ?
C21 C27 N1 C28 179.3(10) . . . . ?
C21 C27 N1 Cu1 -40.5(14) . . . . ?
C1 C7 N1 C27 -75.4(13) . . . . ?
C1 C7 N1 C8 169.2(10) . . . . ?
C1 C7 N1 C28 -152.8(9) . . . . ?
C1 C7 N1 Cu1 27.3(14) . . . . ?
C9 C8 N1 C27 -127.1(10) . . . . ?
C9 C8 N1 C7 -89.1(10) . . . . ?
C9 C8 N1 C28 150.3(14) . . . . ?
C9 C8 N1 Cu1 53.6(10) . . . . ?
C29 C28 N1 C27 -124.1(8) . . . . ?
C29 C28 N1 C7 -86.4(9) . . . . ?
C29 C28 N1 C8 -10.0(7) . . . . ?
C29 C28 N1 Cu1 93.5(6) . . . . ?
C5 C6 O1 C26 168.5(16) . . . . ?
C1 C6 O1 C26 -12.3(14) . . . . ?
C5 C6 O1 Cu1 -153.1(3) . . . . ?
C1 C6 O1 Cu1 26.1(9) . . . . ?
C21 C26 O1 C6 136.7(19) . . . . ?
C25 C26 O1 C6 -43.3(15) . . . . ?
C21 C26 O1 Cu1 -10.5(11) . . . . ?
C25 C26 O1 Cu1 169.5(2) . . . . ?
O3 C11 O2 Cu1 178.0(3) 2_645 . . . ?
C30 C11 O2 Cu1 20.4(7) . . . . ?
C10 C11 O2 Cu1 -13.9(6) . . . . ?
C6 O1 Cu1 N1 -18.6(5) . . . . ?
C26 O1 Cu1 N1 -9.9(4) . . . . ?
C6 O1 Cu1 O3 165.5(5) . . . . ?
C26 O1 Cu1 O3 174.3(4) . . . . ?
C6 O1 Cu1 O2 -135.7(6) . . . . ?
C26 O1 Cu1 O2 -126.9(6) . . . . ?
C6 O1 Cu1 O5 71.3(5) . . . . ?
C26 O1 Cu1 O5 80.1(4) . . . . ?
C27 N1 Cu1 O1 33.8(7) . . . . ?
C7 N1 Cu1 O1 -8.9(7) . . . . ?
C8 N1 Cu1 O1 -147.0(6) . . . . ?
C28 N1 Cu1 O1 171.2(5) . . . . ?
C27 N1 Cu1 O3 76.5(15) . . . . ?
C7 N1 Cu1 O3 33.9(16) . . . . ?
C8 N1 Cu1 O3 -104.2(13) . . . . ?
C28 N1 Cu1 O3 -146.0(12) . . . . ?
C27 N1 Cu1 O2 -156.1(7) . . . . ?
C7 N1 Cu1 O2 161.3(6) . . . . ?
C8 N1 Cu1 O2 23.2(6) . . . . ?
C28 N1 Cu1 O2 -18.6(5) . . . . ?
C27 N1 Cu1 O5 -63.6(7) . . . . ?
C7 N1 Cu1 O5 -106.2(6) . . . . ?
C8 N1 Cu1 O5 115.7(6) . . . . ?
C28 N1 Cu1 O5 73.9(5) . . . . ?
C11 O3 Cu1 O1 117.2(3) 2_655 . . . ?
C11 O3 Cu1 N1 74.2(13) 2_655 . . . ?
C11 O3 Cu1 O2 -53.4(3) 2_655 . . . ?
C11 O3 Cu1 O5 -145.9(3) 2_655 . . . ?
C11 O2 Cu1 O1 60.4(8) . . . . ?
C11 O2 Cu1 N1 -56.5(3) . . . . ?
C11 O2 Cu1 O3 118.6(3) . . . . ?
C11 O2 Cu1 O5 -146.4(3) . . . . ?

_diffrn_measured_fraction_theta_max 0.997
_diffrn_reflns_theta_full        26.37
_diffrn_measured_fraction_theta_full 0.997
_refine_diff_density_max         0.750
_refine_diff_density_min         -0.616
_refine_diff_density_rms         0.085