# Electronic Supplementary Material (ESI) for New Journal of Chemistry
# This journal is © The Royal Society of Chemistry and The Centre National de la Recherche Scientifique 2012


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#                                CCDC 
# 
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# 
#  This CIF contains data from an original supplementary publication 
#  deposited with the CCDC, and may include chemical, crystal,   
#  experimental, refinement, atomic coordinates, 
#  anisotropic displacement parameters and molecular geometry data,
#  as required by the journal to which it was submitted. 
# 
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#  fide research purposes only. It may contain copyright material 
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data_a25
_database_code_depnum_ccdc_archive 'CCDC 857810'
#TrackingRef 'a25.cif'


_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C23 H26 Cl Cu2 N5 O10'
_chemical_formula_weight         695.02

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'
Cl Cl 0.1484 0.1585 '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                   10.2352(2)
_cell_length_b                   11.7803(2)
_cell_length_c                   12.9715(2)
_cell_angle_alpha                79.1190(10)
_cell_angle_beta                 71.6090(10)
_cell_angle_gamma                64.3420(10)
_cell_volume                     1335.31(4)
_cell_formula_units_Z            2
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    ?
_cell_measurement_theta_min      ?
_cell_measurement_theta_max      ?

_exptl_crystal_description       ?
_exptl_crystal_colour            ?
_exptl_crystal_size_max          0.12
_exptl_crystal_size_mid          0.07
_exptl_crystal_size_min          0.05
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.729
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             708
_exptl_absorpt_coefficient_mu    1.759
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.8167
_exptl_absorpt_correction_T_max  0.9172
_exptl_absorpt_process_details   ?

_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  ?
_diffrn_measurement_method       ?
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            10326
_diffrn_reflns_av_R_equivalents  0.0246
_diffrn_reflns_av_sigmaI/netI    0.0369
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_theta_min         2.33
_diffrn_reflns_theta_max         25.24
_reflns_number_total             4814
_reflns_number_gt                3453
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    ?
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    ?
_computing_publication_material  ?

_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
[0.00000+1.00000exp(0.12(sin\q/\l)^2^)]/
[\s^2^(Fo^2^)+0.0000+1.0560*P+(0.0597P)^2^+0.0000sin\q/\l]
where P = 0.33333Fo^2^ + 0.66667Fc^2^
;
_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         4814
_refine_ls_number_parameters     398
_refine_ls_number_restraints     73
_refine_ls_R_factor_all          0.0698
_refine_ls_R_factor_gt           0.0446
_refine_ls_wR_factor_ref         0.1237
_refine_ls_wR_factor_gt          0.1094
_refine_ls_goodness_of_fit_ref   1.035
_refine_ls_restrained_S_all      1.078
_refine_ls_shift/su_max          0.003
_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 0.47114(6) 0.23325(5) 0.89208(4) 0.04810(18) Uani 1 1 d . . .
Cu2 Cu 0.30879(6) 0.05992(5) 0.63575(4) 0.05172(19) Uani 1 1 d . . .
O1 O 0.6442(3) 0.1380(3) 0.9508(2) 0.0529(8) Uani 1 1 d . . .
O2 O 0.4632(3) -0.0074(3) 0.7168(2) 0.0497(7) Uani 1 1 d . . .
O3 O 0.2553(4) 0.2217(3) 0.6893(3) 0.0605(8) Uani 1 1 d . . .
O4 O 0.1502(4) -0.0082(3) 0.7634(2) 0.0656(9) Uani 1 1 d . . .
H4A H 0.1942 -0.0757 0.8105 0.098 Uiso 1 1 d R . .
H4B H 0.0846 0.0573 0.8044 0.098 Uiso 1 1 d R . .
N1 N 0.5199(4) 0.0741(3) 0.8391(3) 0.0422(8) Uani 1 1 d . . .
N2 N 0.3298(4) 0.2993(3) 0.8010(3) 0.0536(9) Uani 1 1 d . . .
N3 N 0.4221(5) 0.3979(3) 0.9449(3) 0.0610(10) Uani 1 1 d . . .
H3A H 0.4177 0.3863 1.0163 0.073 Uiso 1 1 calc R . .
H3B H 0.4990 0.4212 0.9108 0.073 Uiso 1 1 calc R . .
N4 N 0.3785(4) -0.0950(4) 0.5562(3) 0.0522(9) Uani 1 1 d . . .
N5 N 0.1804(4) 0.1381(4) 0.5323(3) 0.0543(9) Uani 1 1 d . . .
C1 C 0.7001(5) 0.0147(4) 0.9336(3) 0.0478(10) Uani 1 1 d . . .
C2 C 0.6377(4) -0.0260(4) 0.8733(3) 0.0416(9) Uani 1 1 d . . .
C3 C 0.6947(5) -0.1530(4) 0.8533(3) 0.0503(10) Uani 1 1 d . . .
H3 H 0.6521 -0.1796 0.8141 0.060 Uiso 1 1 calc R . .
C4 C 0.8152(5) -0.2397(4) 0.8921(4) 0.0568(12) Uani 1 1 d . . .
H4 H 0.8539 -0.3247 0.8792 0.068 Uiso 1 1 calc R . .
C5 C 0.8771(5) -0.1984(5) 0.9504(4) 0.0607(13) Uani 1 1 d . . .
H5 H 0.9582 -0.2563 0.9761 0.073 Uiso 1 1 calc R . .
C6 C 0.8213(5) -0.0738(5) 0.9708(4) 0.0547(12) Uani 1 1 d . . .
H6 H 0.8649 -0.0483 1.0099 0.066 Uiso 1 1 calc R . .
C7 C 0.4479(4) 0.0793(4) 0.7710(3) 0.0426(9) Uani 1 1 d . . .
C8 C 0.3333(5) 0.2108(4) 0.7535(3) 0.0495(11) Uani 1 1 d . . .
C9 C 0.2220(6) 0.4284(4) 0.7879(5) 0.0709(15) Uani 1 1 d . . .
H9A H 0.1234 0.4373 0.8343 0.085 Uiso 1 1 calc R . .
H9B H 0.2156 0.4462 0.7130 0.085 Uiso 1 1 calc R . .
C10 C 0.2672(7) 0.5217(5) 0.8166(5) 0.0726(15) Uani 1 1 d . . .
H10A H 0.3633 0.5151 0.7670 0.087 Uiso 1 1 calc R . .
H10B H 0.1940 0.6061 0.8052 0.087 Uiso 1 1 calc R . .
C11 C 0.2800(6) 0.5055(4) 0.9306(4) 0.0690(14) Uani 1 1 d . . .
H11A H 0.1946 0.4907 0.9801 0.083 Uiso 1 1 calc R . .
H11B H 0.2771 0.5826 0.9494 0.083 Uiso 1 1 calc R . .
C12 C 0.4749(6) -0.2090(5) 0.5712(4) 0.0660(13) Uani 1 1 d . . .
H12 H 0.5324 -0.2236 0.6192 0.079 Uiso 1 1 calc R . .
C13 C 0.4954(7) -0.3111(6) 0.5176(4) 0.0759(15) Uani 1 1 d . . .
H13 H 0.5660 -0.3914 0.5296 0.091 Uiso 1 1 calc R . .
C14 C 0.4118(7) -0.2916(6) 0.4485(4) 0.0774(16) Uani 1 1 d . . .
H14 H 0.4234 -0.3589 0.4137 0.093 Uiso 1 1 calc R . .
C15 C 0.3068(6) -0.1692(5) 0.4294(4) 0.0598(13) Uani 1 1 d . . .
C16 C 0.2127(7) -0.1354(7) 0.3565(4) 0.0734(16) Uani 1 1 d . . .
H16 H 0.2189 -0.1978 0.3185 0.088 Uiso 1 1 calc R . .
C17 C 0.1175(7) -0.0173(7) 0.3424(4) 0.0711(16) Uani 1 1 d . . .
H17 H 0.0595 0.0012 0.2940 0.085 Uiso 1 1 calc R . .
C18 C 0.1020(5) 0.0816(5) 0.3994(3) 0.0593(13) Uani 1 1 d . . .
C19 C 0.0063(6) 0.2070(6) 0.3890(4) 0.0719(15) Uani 1 1 d . . .
H19 H -0.0530 0.2317 0.3407 0.086 Uiso 1 1 calc R . .
C20 C -0.0023(6) 0.2941(6) 0.4479(5) 0.0802(17) Uani 1 1 d . . .
H20 H -0.0667 0.3782 0.4400 0.096 Uiso 1 1 calc R . .
C21 C 0.0867(6) 0.2567(5) 0.5210(4) 0.0657(13) Uani 1 1 d . . .
H21 H 0.0796 0.3165 0.5624 0.079 Uiso 1 1 calc R . .
C22 C 0.1903(5) 0.0514(5) 0.4726(3) 0.0525(11) Uani 1 1 d . . .
C23 C 0.2946(5) -0.0753(5) 0.4864(3) 0.0514(11) Uani 1 1 d . . .
O5 O 0.9141(4) 0.1851(4) 0.8730(3) 0.0854(11) Uani 1 1 d . . .
H5A H 0.8946 0.2628 0.8373 0.128 Uiso 1 1 d R . .
H5B H 0.8275 0.1767 0.8938 0.128 Uiso 1 1 d R . .
O6 O 0.6739(5) 0.2111(4) 1.1259(3) 0.0866(12) Uani 1 1 d . . .
H6A H 0.5971 0.2784 1.1555 0.130 Uiso 1 1 d R . .
H6B H 0.6439 0.1956 1.0775 0.130 Uiso 1 1 d R . .
Cl1 Cl 0.74443(14) 0.50481(11) 0.73598(11) 0.0640(3) Uani 1 1 d D . .
O7 O 0.8721(6) 0.4514(5) 0.7715(6) 0.176(3) Uani 1 1 d D A .
O8A O 0.6226(12) 0.532(2) 0.8329(10) 0.150(10) Uani 0.253(13) 1 d PDU A 1
O9A O 0.7276(17) 0.4351(15) 0.6763(16) 0.104(8) Uani 0.253(13) 1 d PDU A 1
O10A O 0.734(2) 0.6222(14) 0.684(2) 0.122(10) Uani 0.253(13) 1 d PDU A 1
O8B O 0.6402(8) 0.6132(6) 0.7859(8) 0.134(4) Uani 0.747(13) 1 d PDU A 2
O9B O 0.6815(8) 0.4165(6) 0.7531(9) 0.151(4) Uani 0.747(13) 1 d PDU A 2
O10B O 0.7856(9) 0.5313(10) 0.6238(5) 0.159(4) Uani 0.747(13) 1 d PDU A 2

loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_23
_atom_site_aniso_U_13
_atom_site_aniso_U_12
Cu1 0.0450(3) 0.0503(3) 0.0532(3) -0.0113(2) -0.0229(3) -0.0127(2)
Cu2 0.0516(3) 0.0662(4) 0.0492(3) -0.0080(3) -0.0250(3) -0.0244(3)
O1 0.0468(17) 0.0590(19) 0.0586(19) -0.0159(14) -0.0266(15) -0.0127(15)
O2 0.0466(17) 0.0560(18) 0.0543(18) -0.0109(14) -0.0239(14) -0.0173(14)
O3 0.0579(19) 0.0608(19) 0.073(2) -0.0082(16) -0.0405(17) -0.0148(16)
O4 0.059(2) 0.092(2) 0.0520(19) -0.0041(17) -0.0196(16) -0.0332(19)
N1 0.0380(18) 0.051(2) 0.0425(19) -0.0074(15) -0.0159(15) -0.0164(16)
N2 0.051(2) 0.048(2) 0.065(2) -0.0087(18) -0.0298(19) -0.0114(17)
N3 0.065(3) 0.055(2) 0.069(3) -0.0129(19) -0.027(2) -0.020(2)
N4 0.052(2) 0.070(3) 0.042(2) -0.0104(17) -0.0151(17) -0.027(2)
N5 0.054(2) 0.072(3) 0.050(2) 0.0017(19) -0.0243(18) -0.031(2)
C1 0.047(2) 0.058(3) 0.038(2) -0.0107(19) -0.0062(19) -0.021(2)
C2 0.033(2) 0.054(2) 0.037(2) 0.0005(18) -0.0093(17) -0.0170(19)
C3 0.050(3) 0.057(3) 0.048(3) -0.007(2) -0.013(2) -0.025(2)
C4 0.055(3) 0.042(2) 0.062(3) 0.000(2) -0.017(2) -0.010(2)
C5 0.047(3) 0.068(3) 0.057(3) 0.002(2) -0.025(2) -0.008(2)
C6 0.048(3) 0.069(3) 0.051(3) -0.010(2) -0.026(2) -0.016(2)
C7 0.037(2) 0.050(2) 0.047(2) -0.0075(19) -0.0146(19) -0.0184(19)
C8 0.042(2) 0.058(3) 0.051(3) -0.004(2) -0.022(2) -0.015(2)
C9 0.066(3) 0.056(3) 0.091(4) -0.012(3) -0.042(3) -0.007(3)
C10 0.078(4) 0.049(3) 0.085(4) -0.010(3) -0.034(3) -0.010(3)
C11 0.076(4) 0.049(3) 0.078(4) -0.015(2) -0.026(3) -0.013(3)
C12 0.069(3) 0.075(3) 0.054(3) -0.013(2) -0.022(3) -0.021(3)
C13 0.074(4) 0.076(4) 0.068(4) -0.017(3) -0.017(3) -0.018(3)
C14 0.089(4) 0.095(4) 0.064(3) -0.028(3) -0.007(3) -0.052(4)
C15 0.062(3) 0.090(4) 0.042(3) -0.012(2) -0.007(2) -0.046(3)
C16 0.084(4) 0.125(5) 0.039(3) -0.018(3) -0.009(3) -0.067(4)
C17 0.073(4) 0.129(5) 0.037(3) -0.004(3) -0.018(3) -0.061(4)
C18 0.055(3) 0.101(4) 0.034(2) 0.005(2) -0.013(2) -0.045(3)
C19 0.068(3) 0.111(5) 0.051(3) 0.015(3) -0.032(3) -0.045(3)
C20 0.071(4) 0.093(4) 0.080(4) 0.026(3) -0.040(3) -0.035(3)
C21 0.067(3) 0.075(4) 0.064(3) 0.005(3) -0.028(3) -0.034(3)
C22 0.052(3) 0.088(3) 0.031(2) -0.001(2) -0.0107(19) -0.042(3)
C23 0.049(3) 0.082(3) 0.035(2) -0.009(2) -0.010(2) -0.035(2)
O5 0.067(2) 0.078(3) 0.105(3) 0.007(2) -0.031(2) -0.023(2)
O6 0.118(3) 0.082(3) 0.075(3) -0.010(2) -0.042(2) -0.041(2)
Cl1 0.0665(8) 0.0537(7) 0.0755(9) -0.0118(6) -0.0269(7) -0.0186(6)
O7 0.137(5) 0.128(5) 0.295(9) -0.024(5) -0.148(6) -0.016(4)
O8A 0.162(16) 0.22(2) 0.102(14) -0.066(13) 0.032(11) -0.136(15)
O9A 0.113(11) 0.111(11) 0.123(12) -0.058(8) -0.028(8) -0.059(8)
O10A 0.134(16) 0.119(15) 0.136(18) 0.050(13) -0.063(13) -0.076(13)
O8B 0.133(6) 0.088(5) 0.163(8) -0.069(5) -0.065(6) 0.016(4)
O9B 0.125(6) 0.115(6) 0.217(10) -0.028(6) 0.000(6) -0.077(5)
O10B 0.158(7) 0.161(9) 0.099(6) 0.012(5) -0.007(5) -0.036(6)

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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Cu1 N1 1.922(3) . ?
Cu1 O1 1.945(3) . ?
Cu1 N2 1.963(3) . ?
Cu1 N3 1.982(4) . ?
Cu2 O3 1.941(3) . ?
Cu2 O2 1.970(3) . ?
Cu2 N5 1.993(3) . ?
Cu2 N4 2.005(4) . ?
Cu2 O4 2.225(3) . ?
O1 C1 1.344(5) . ?
O2 C7 1.275(5) . ?
O3 C8 1.280(5) . ?
O4 H4A 0.9426 . ?
O4 H4B 0.9003 . ?
N1 C7 1.296(5) . ?
N1 C2 1.396(5) . ?
N2 C8 1.289(5) . ?
N2 C9 1.458(6) . ?
N3 C11 1.497(6) . ?
N3 H3A 0.9000 . ?
N3 H3B 0.9000 . ?
N4 C12 1.300(6) . ?
N4 C23 1.360(5) . ?
N5 C21 1.321(6) . ?
N5 C22 1.346(6) . ?
C1 C6 1.388(6) . ?
C1 C2 1.404(6) . ?
C2 C3 1.394(6) . ?
C3 C4 1.387(6) . ?
C3 H3 0.9300 . ?
C4 C5 1.385(7) . ?
C4 H4 0.9300 . ?
C5 C6 1.369(7) . ?
C5 H5 0.9300 . ?
C6 H6 0.9300 . ?
C7 C8 1.513(6) . ?
C9 C10 1.506(7) . ?
C9 H9A 0.9700 . ?
C9 H9B 0.9700 . ?
C10 C11 1.495(7) . ?
C10 H10A 0.9700 . ?
C10 H10B 0.9700 . ?
C11 H11A 0.9700 . ?
C11 H11B 0.9700 . ?
C12 C13 1.406(7) . ?
C12 H12 0.9300 . ?
C13 C14 1.351(8) . ?
C13 H13 0.9300 . ?
C14 C15 1.409(8) . ?
C14 H14 0.9300 . ?
C15 C23 1.384(6) . ?
C15 C16 1.442(7) . ?
C16 C17 1.327(8) . ?
C16 H16 0.9300 . ?
C17 C18 1.421(7) . ?
C17 H17 0.9300 . ?
C18 C19 1.384(7) . ?
C18 C22 1.408(6) . ?
C19 C20 1.349(8) . ?
C19 H19 0.9300 . ?
C20 C21 1.400(7) . ?
C20 H20 0.9300 . ?
C21 H21 0.9300 . ?
C22 C23 1.428(7) . ?
O5 H5A 0.9117 . ?
O5 H5B 0.8854 . ?
O6 H6A 0.8822 . ?
O6 H6B 0.8574 . ?
Cl1 O9A 1.322(8) . ?
Cl1 O7 1.369(4) . ?
Cl1 O8B 1.373(5) . ?
Cl1 O10A 1.394(9) . ?
Cl1 O10B 1.396(5) . ?
Cl1 O9B 1.397(6) . ?
Cl1 O8A 1.434(9) . ?

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
N1 Cu1 O1 83.91(13) . . ?
N1 Cu1 N2 83.63(14) . . ?
O1 Cu1 N2 164.67(13) . . ?
N1 Cu1 N3 179.30(17) . . ?
O1 Cu1 N3 96.19(14) . . ?
N2 Cu1 N3 96.16(15) . . ?
O3 Cu2 O2 85.73(12) . . ?
O3 Cu2 N5 92.64(14) . . ?
O2 Cu2 N5 169.26(14) . . ?
O3 Cu2 N4 170.37(14) . . ?
O2 Cu2 N4 97.12(13) . . ?
N5 Cu2 N4 82.84(16) . . ?
O3 Cu2 O4 100.55(14) . . ?
O2 Cu2 O4 93.90(12) . . ?
N5 Cu2 O4 96.84(14) . . ?
N4 Cu2 O4 88.47(14) . . ?
C1 O1 Cu1 110.9(2) . . ?
C7 O2 Cu2 109.3(2) . . ?
C8 O3 Cu2 111.2(3) . . ?
Cu2 O4 H4A 115.5 . . ?
Cu2 O4 H4B 106.8 . . ?
H4A O4 H4B 107.4 . . ?
C7 N1 C2 130.8(4) . . ?
C7 N1 Cu1 115.2(3) . . ?
C2 N1 Cu1 113.7(3) . . ?
C8 N2 C9 119.6(4) . . ?
C8 N2 Cu1 111.8(3) . . ?
C9 N2 Cu1 128.5(3) . . ?
C11 N3 Cu1 117.6(3) . . ?
C11 N3 H3A 107.9 . . ?
Cu1 N3 H3A 107.9 . . ?
C11 N3 H3B 107.9 . . ?
Cu1 N3 H3B 107.9 . . ?
H3A N3 H3B 107.2 . . ?
C12 N4 C23 118.1(4) . . ?
C12 N4 Cu2 130.0(3) . . ?
C23 N4 Cu2 111.3(3) . . ?
C21 N5 C22 119.3(4) . . ?
C21 N5 Cu2 128.9(3) . . ?
C22 N5 Cu2 111.6(3) . . ?
O1 C1 C6 122.1(4) . . ?
O1 C1 C2 119.4(4) . . ?
C6 C1 C2 118.5(4) . . ?
C3 C2 N1 127.6(4) . . ?
C3 C2 C1 120.5(4) . . ?
N1 C2 C1 111.8(4) . . ?
C4 C3 C2 119.7(4) . . ?
C4 C3 H3 120.1 . . ?
C2 C3 H3 120.1 . . ?
C5 C4 C3 119.3(4) . . ?
C5 C4 H4 120.3 . . ?
C3 C4 H4 120.3 . . ?
C6 C5 C4 121.3(4) . . ?
C6 C5 H5 119.4 . . ?
C4 C5 H5 119.4 . . ?
C5 C6 C1 120.7(4) . . ?
C5 C6 H6 119.7 . . ?
C1 C6 H6 119.7 . . ?
O2 C7 N1 129.7(4) . . ?
O2 C7 C8 117.7(3) . . ?
N1 C7 C8 112.6(4) . . ?
O3 C8 N2 127.6(4) . . ?
O3 C8 C7 115.7(4) . . ?
N2 C8 C7 116.6(4) . . ?
N2 C9 C10 111.2(4) . . ?
N2 C9 H9A 109.4 . . ?
C10 C9 H9A 109.4 . . ?
N2 C9 H9B 109.4 . . ?
C10 C9 H9B 109.4 . . ?
H9A C9 H9B 108.0 . . ?
C11 C10 C9 115.0(5) . . ?
C11 C10 H10A 108.5 . . ?
C9 C10 H10A 108.5 . . ?
C11 C10 H10B 108.5 . . ?
C9 C10 H10B 108.5 . . ?
H10A C10 H10B 107.5 . . ?
C10 C11 N3 112.1(4) . . ?
C10 C11 H11A 109.2 . . ?
N3 C11 H11A 109.2 . . ?
C10 C11 H11B 109.2 . . ?
N3 C11 H11B 109.2 . . ?
H11A C11 H11B 107.9 . . ?
N4 C12 C13 122.4(5) . . ?
N4 C12 H12 118.8 . . ?
C13 C12 H12 118.8 . . ?
C14 C13 C12 119.5(5) . . ?
C14 C13 H13 120.2 . . ?
C12 C13 H13 120.2 . . ?
C13 C14 C15 119.8(5) . . ?
C13 C14 H14 120.1 . . ?
C15 C14 H14 120.1 . . ?
C23 C15 C14 116.2(4) . . ?
C23 C15 C16 118.4(5) . . ?
C14 C15 C16 125.4(5) . . ?
C17 C16 C15 121.6(5) . . ?
C17 C16 H16 119.2 . . ?
C15 C16 H16 119.2 . . ?
C16 C17 C18 121.6(5) . . ?
C16 C17 H17 119.2 . . ?
C18 C17 H17 119.2 . . ?
C19 C18 C22 116.4(5) . . ?
C19 C18 C17 125.3(5) . . ?
C22 C18 C17 118.3(5) . . ?
C20 C19 C18 121.0(5) . . ?
C20 C19 H19 119.5 . . ?
C18 C19 H19 119.5 . . ?
C19 C20 C21 119.3(6) . . ?
C19 C20 H20 120.3 . . ?
C21 C20 H20 120.3 . . ?
N5 C21 C20 121.4(5) . . ?
N5 C21 H21 119.3 . . ?
C20 C21 H21 119.3 . . ?
N5 C22 C18 122.5(5) . . ?
N5 C22 C23 117.4(4) . . ?
C18 C22 C23 120.1(4) . . ?
N4 C23 C15 123.9(5) . . ?
N4 C23 C22 116.0(4) . . ?
C15 C23 C22 120.1(4) . . ?
H5A O5 H5B 105.2 . . ?
H6A O6 H6B 103.5 . . ?
O9A Cl1 O7 116.5(6) . . ?
O9A Cl1 O8B 129.0(7) . . ?
O7 Cl1 O8B 113.2(4) . . ?
O9A Cl1 O10A 112.1(6) . . ?
O7 Cl1 O10A 108.4(5) . . ?
O8B Cl1 O10A 59.9(9) . . ?
O9A Cl1 O10B 65.0(8) . . ?
O7 Cl1 O10B 108.1(4) . . ?
O8B Cl1 O10B 109.6(4) . . ?
O10A Cl1 O10B 54.0(9) . . ?
O9A Cl1 O9B 42.4(8) . . ?
O7 Cl1 O9B 108.8(4) . . ?
O8B Cl1 O9B 109.9(4) . . ?
O10A Cl1 O9B 142.1(6) . . ?
O10B Cl1 O9B 107.0(4) . . ?
O9A Cl1 O8A 108.8(6) . . ?
O7 Cl1 O8A 105.2(6) . . ?
O8B Cl1 O8A 45.3(8) . . ?
O10A Cl1 O8A 105.0(6) . . ?
O10B Cl1 O8A 145.0(7) . . ?
O9B Cl1 O8A 71.4(8) . . ?

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
N1 Cu1 O1 C1 -4.7(3) . . . . ?
N2 Cu1 O1 C1 -40.5(7) . . . . ?
N3 Cu1 O1 C1 176.0(3) . . . . ?
O3 Cu2 O2 C7 5.4(3) . . . . ?
N5 Cu2 O2 C7 87.0(8) . . . . ?
N4 Cu2 O2 C7 176.1(3) . . . . ?
O4 Cu2 O2 C7 -94.9(3) . . . . ?
O2 Cu2 O3 C8 -3.4(3) . . . . ?
N5 Cu2 O3 C8 -172.8(3) . . . . ?
N4 Cu2 O3 C8 -111.1(8) . . . . ?
O4 Cu2 O3 C8 89.7(3) . . . . ?
O1 Cu1 N1 C7 -169.7(3) . . . . ?
N2 Cu1 N1 C7 1.4(3) . . . . ?
N3 Cu1 N1 C7 -71(13) . . . . ?
O1 Cu1 N1 C2 4.7(3) . . . . ?
N2 Cu1 N1 C2 175.8(3) . . . . ?
N3 Cu1 N1 C2 103(12) . . . . ?
N1 Cu1 N2 C8 1.3(3) . . . . ?
O1 Cu1 N2 C8 37.1(8) . . . . ?
N3 Cu1 N2 C8 -179.4(3) . . . . ?
N1 Cu1 N2 C9 177.4(4) . . . . ?
O1 Cu1 N2 C9 -146.8(5) . . . . ?
N3 Cu1 N2 C9 -3.3(5) . . . . ?
N1 Cu1 N3 C11 88(13) . . . . ?
O1 Cu1 N3 C11 -173.1(4) . . . . ?
N2 Cu1 N3 C11 16.0(4) . . . . ?
O3 Cu2 N4 C12 118.7(8) . . . . ?
O2 Cu2 N4 C12 12.0(5) . . . . ?
N5 Cu2 N4 C12 -178.8(5) . . . . ?
O4 Cu2 N4 C12 -81.8(4) . . . . ?
O3 Cu2 N4 C23 -70.3(9) . . . . ?
O2 Cu2 N4 C23 -177.1(3) . . . . ?
N5 Cu2 N4 C23 -7.9(3) . . . . ?
O4 Cu2 N4 C23 89.2(3) . . . . ?
O3 Cu2 N5 C21 -5.8(4) . . . . ?
O2 Cu2 N5 C21 -86.8(9) . . . . ?
N4 Cu2 N5 C21 -177.3(4) . . . . ?
O4 Cu2 N5 C21 95.1(4) . . . . ?
O3 Cu2 N5 C22 178.1(3) . . . . ?
O2 Cu2 N5 C22 97.1(8) . . . . ?
N4 Cu2 N5 C22 6.7(3) . . . . ?
O4 Cu2 N5 C22 -80.9(3) . . . . ?
Cu1 O1 C1 C6 -178.0(3) . . . . ?
Cu1 O1 C1 C2 4.0(5) . . . . ?
C7 N1 C2 C3 -9.9(7) . . . . ?
Cu1 N1 C2 C3 176.8(3) . . . . ?
C7 N1 C2 C1 169.5(4) . . . . ?
Cu1 N1 C2 C1 -3.8(4) . . . . ?
O1 C1 C2 C3 179.3(4) . . . . ?
C6 C1 C2 C3 1.2(6) . . . . ?
O1 C1 C2 N1 -0.2(5) . . . . ?
C6 C1 C2 N1 -178.3(4) . . . . ?
N1 C2 C3 C4 178.6(4) . . . . ?
C1 C2 C3 C4 -0.8(6) . . . . ?
C2 C3 C4 C5 0.0(7) . . . . ?
C3 C4 C5 C6 0.3(7) . . . . ?
C4 C5 C6 C1 0.2(7) . . . . ?
O1 C1 C6 C5 -178.9(4) . . . . ?
C2 C1 C6 C5 -0.9(7) . . . . ?
Cu2 O2 C7 N1 176.1(4) . . . . ?
Cu2 O2 C7 C8 -6.2(4) . . . . ?
C2 N1 C7 O2 1.3(8) . . . . ?
Cu1 N1 C7 O2 174.5(4) . . . . ?
C2 N1 C7 C8 -176.6(4) . . . . ?
Cu1 N1 C7 C8 -3.3(5) . . . . ?
Cu2 O3 C8 N2 178.0(4) . . . . ?
Cu2 O3 C8 C7 1.1(5) . . . . ?
C9 N2 C8 O3 3.2(8) . . . . ?
Cu1 N2 C8 O3 179.7(4) . . . . ?
C9 N2 C8 C7 -179.9(4) . . . . ?
Cu1 N2 C8 C7 -3.4(5) . . . . ?
O2 C7 C8 O3 3.7(6) . . . . ?
N1 C7 C8 O3 -178.2(4) . . . . ?
O2 C7 C8 N2 -173.5(4) . . . . ?
N1 C7 C8 N2 4.6(6) . . . . ?
C8 N2 C9 C10 -161.3(5) . . . . ?
Cu1 N2 C9 C10 22.9(7) . . . . ?
N2 C9 C10 C11 -59.5(6) . . . . ?
C9 C10 C11 N3 77.1(6) . . . . ?
Cu1 N3 C11 C10 -50.3(6) . . . . ?
C23 N4 C12 C13 0.4(7) . . . . ?
Cu2 N4 C12 C13 170.9(4) . . . . ?
N4 C12 C13 C14 -0.6(9) . . . . ?
C12 C13 C14 C15 1.1(8) . . . . ?
C13 C14 C15 C23 -1.4(8) . . . . ?
C13 C14 C15 C16 178.9(5) . . . . ?
C23 C15 C16 C17 0.9(7) . . . . ?
C14 C15 C16 C17 -179.4(5) . . . . ?
C15 C16 C17 C18 -0.8(8) . . . . ?
C16 C17 C18 C19 179.6(5) . . . . ?
C16 C17 C18 C22 -0.3(7) . . . . ?
C22 C18 C19 C20 -1.0(7) . . . . ?
C17 C18 C19 C20 179.0(5) . . . . ?
C18 C19 C20 C21 -0.3(8) . . . . ?
C22 N5 C21 C20 -0.3(7) . . . . ?
Cu2 N5 C21 C20 -176.0(4) . . . . ?
C19 C20 C21 N5 1.0(8) . . . . ?
C21 N5 C22 C18 -1.2(7) . . . . ?
Cu2 N5 C22 C18 175.3(3) . . . . ?
C21 N5 C22 C23 179.2(4) . . . . ?
Cu2 N5 C22 C23 -4.4(5) . . . . ?
C19 C18 C22 N5 1.8(7) . . . . ?
C17 C18 C22 N5 -178.2(4) . . . . ?
C19 C18 C22 C23 -178.5(4) . . . . ?
C17 C18 C22 C23 1.4(6) . . . . ?
C12 N4 C23 C15 -0.8(7) . . . . ?
Cu2 N4 C23 C15 -172.9(4) . . . . ?
C12 N4 C23 C22 180.0(4) . . . . ?
Cu2 N4 C23 C22 7.8(5) . . . . ?
C14 C15 C23 N4 1.2(7) . . . . ?
C16 C15 C23 N4 -179.0(4) . . . . ?
C14 C15 C23 C22 -179.5(4) . . . . ?
C16 C15 C23 C22 0.2(7) . . . . ?
N5 C22 C23 N4 -2.4(6) . . . . ?
C18 C22 C23 N4 178.0(4) . . . . ?
N5 C22 C23 C15 178.3(4) . . . . ?
C18 C22 C23 C15 -1.4(6) . . . . ?

_diffrn_measured_fraction_theta_max 0.995
_diffrn_reflns_theta_full        25.24
_diffrn_measured_fraction_theta_full 0.995
_refine_diff_density_max         1.152
_refine_diff_density_min         -0.277
_refine_diff_density_rms         0.072




data_a
_database_code_depnum_ccdc_archive 'CCDC 857811'
#TrackingRef 'a.cif'


_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C23 H26 Cu2 N6 O7'
_chemical_formula_weight         625.58

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                   9.876(4)
_cell_length_b                   11.210(4)
_cell_length_c                   11.834(5)
_cell_angle_alpha                92.410(7)
_cell_angle_beta                 110.147(7)
_cell_angle_gamma                95.229(7)
_cell_volume                     1221.1(8)
_cell_formula_units_Z            2
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    ?
_cell_measurement_theta_min      ?
_cell_measurement_theta_max      ?

_exptl_crystal_description       ?
_exptl_crystal_colour            ?
_exptl_crystal_size_max          0.11
_exptl_crystal_size_mid          0.10
_exptl_crystal_size_min          0.06
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.701
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             640
_exptl_absorpt_coefficient_mu    1.799
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.8266
_exptl_absorpt_correction_T_max  0.8997
_exptl_absorpt_process_details   ?

_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  ?
_diffrn_measurement_method       ?
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            6629
_diffrn_reflns_av_R_equivalents  0.0256
_diffrn_reflns_av_sigmaI/netI    0.0619
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_theta_min         2.21
_diffrn_reflns_theta_max         26.15
_reflns_number_total             4809
_reflns_number_gt                3222
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    ?
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    ?
_computing_publication_material  ?

_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^)+(0.0425P)^2^+0.1597P] 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         4809
_refine_ls_number_parameters     353
_refine_ls_number_restraints     2
_refine_ls_R_factor_all          0.0817
_refine_ls_R_factor_gt           0.0443
_refine_ls_wR_factor_ref         0.1021
_refine_ls_wR_factor_gt          0.0885
_refine_ls_goodness_of_fit_ref   1.012
_refine_ls_restrained_S_all      1.012
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
Cu1 Cu 0.55820(5) 0.09400(4) 0.20542(4) 0.02973(15) Uani 1 1 d . . .
Cu2 Cu 0.81484(5) 0.43734(4) 0.54019(4) 0.03285(15) Uani 1 1 d . . .
O1 O 0.3733(3) 0.0998(2) 0.0766(2) 0.0357(7) Uani 1 1 d . . .
O2 O 0.6411(3) 0.4097(2) 0.3965(2) 0.0357(7) Uani 1 1 d . . .
O3 O 0.8605(3) 0.2806(2) 0.4893(2) 0.0365(7) Uani 1 1 d . . .
O4 O 0.6810(3) 0.3491(3) 0.6445(3) 0.0540(9) Uani 1 1 d . . .
O5 O 0.8339(4) 0.2652(3) 0.7833(4) 0.0908(14) Uani 1 1 d . . .
O6 O 0.6092(5) 0.2188(4) 0.7420(4) 0.0933(14) Uani 1 1 d . . .
N1 N 0.5281(3) 0.2518(3) 0.2517(3) 0.0297(8) Uani 1 1 d . . .
N2 N 0.7398(3) 0.1257(3) 0.3445(3) 0.0306(8) Uani 1 1 d . . .
N3 N 0.5826(4) -0.0709(3) 0.1596(3) 0.0351(8) Uani 1 1 d . . .
H3A H 0.4989 -0.1172 0.1482 0.042 Uiso 1 1 calc R . .
H3B H 0.5956 -0.0709 0.0880 0.042 Uiso 1 1 calc R . .
N4 N 0.7828(4) 0.6049(3) 0.5689(3) 0.0326(8) Uani 1 1 d . . .
N5 N 1.0026(3) 0.4886(3) 0.6683(3) 0.0329(8) Uani 1 1 d . . .
N6 N 0.7098(5) 0.2770(3) 0.7243(4) 0.0466(10) Uani 1 1 d . . .
C1 C 0.3155(4) 0.2012(3) 0.0876(3) 0.0306(9) Uani 1 1 d . . .
C2 C 0.3968(4) 0.2906(3) 0.1810(3) 0.0270(9) Uani 1 1 d . . .
C3 C 0.3438(4) 0.3972(3) 0.1930(3) 0.0320(9) Uani 1 1 d . . .
H3 H 0.3989 0.4554 0.2537 0.038 Uiso 1 1 calc R . .
C4 C 0.2097(4) 0.4187(4) 0.1159(4) 0.0374(10) Uani 1 1 d . . .
H4 H 0.1743 0.4914 0.1242 0.045 Uiso 1 1 calc R . .
C5 C 0.1277(5) 0.3322(4) 0.0261(4) 0.0418(11) Uani 1 1 d . . .
H5 H 0.0365 0.3465 -0.0252 0.050 Uiso 1 1 calc R . .
C6 C 0.1796(4) 0.2252(4) 0.0118(4) 0.0383(10) Uani 1 1 d . . .
H6 H 0.1231 0.1679 -0.0494 0.046 Uiso 1 1 calc R . .
C7 C 0.6307(4) 0.3064(3) 0.3454(3) 0.0284(9) Uani 1 1 d . . .
C8 C 0.7541(4) 0.2314(3) 0.3981(3) 0.0294(9) Uani 1 1 d . . .
C9 C 0.8526(4) 0.0463(3) 0.3880(4) 0.0377(10) Uani 1 1 d . . .
H9A H 0.8418 0.0073 0.4565 0.045 Uiso 1 1 calc R . .
H9B H 0.9471 0.0931 0.4147 0.045 Uiso 1 1 calc R . .
C10 C 0.8431(5) -0.0476(4) 0.2896(4) 0.0461(12) Uani 1 1 d . . .
H10A H 0.9217 -0.0969 0.3202 0.055 Uiso 1 1 calc R . .
H10B H 0.8568 -0.0075 0.2227 0.055 Uiso 1 1 calc R . .
C11 C 0.7012(5) -0.1285(4) 0.2431(4) 0.0478(12) Uani 1 1 d . . .
H11A H 0.7146 -0.2009 0.2021 0.057 Uiso 1 1 calc R . .
H11B H 0.6742 -0.1521 0.3111 0.057 Uiso 1 1 calc R . .
C12 C 0.6656(5) 0.6580(4) 0.5119(4) 0.0393(10) Uani 1 1 d . . .
H12 H 0.5914 0.6146 0.4482 0.047 Uiso 1 1 calc R . .
C13 C 0.6494(5) 0.7736(4) 0.5426(4) 0.0421(11) Uani 1 1 d . . .
H13 H 0.5660 0.8075 0.4999 0.051 Uiso 1 1 calc R . .
C14 C 0.7579(5) 0.8396(3) 0.6376(4) 0.0362(10) Uani 1 1 d . . .
C15 C 0.8786(5) 0.7836(4) 0.6972(4) 0.0362(10) Uani 1 1 d . . .
H15 H 0.9535 0.8249 0.7619 0.043 Uiso 1 1 calc R . .
C16 C 0.8892(4) 0.6680(3) 0.6623(3) 0.0300(9) Uani 1 1 d . . .
C17 C 1.0143(4) 0.6012(3) 0.7184(3) 0.0286(9) Uani 1 1 d . . .
C18 C 1.1340(4) 0.6467(4) 0.8162(3) 0.0326(9) Uani 1 1 d . . .
H18 H 1.1389 0.7242 0.8498 0.039 Uiso 1 1 calc R . .
C19 C 1.2464(4) 0.5788(4) 0.8649(4) 0.0348(10) Uani 1 1 d . . .
C20 C 1.2347(5) 0.4651(4) 0.8107(4) 0.0459(12) Uani 1 1 d . . .
H20 H 1.3091 0.4168 0.8393 0.055 Uiso 1 1 calc R . .
C21 C 1.1117(5) 0.4235(4) 0.7136(4) 0.0405(11) Uani 1 1 d . . .
H21 H 1.1049 0.3464 0.6785 0.049 Uiso 1 1 calc R . .
C22 C 0.7424(5) 0.9647(4) 0.6757(4) 0.0496(12) Uani 1 1 d . . .
H22A H 0.6956 0.9624 0.7346 0.074 Uiso 1 1 calc R . .
H22B H 0.6850 1.0025 0.6068 0.074 Uiso 1 1 calc R . .
H22C H 0.8367 1.0095 0.7103 0.074 Uiso 1 1 calc R . .
C23 C 1.3745(5) 0.6265(4) 0.9735(4) 0.0479(12) Uani 1 1 d . . .
H23A H 1.3714 0.5851 1.0421 0.072 Uiso 1 1 calc R . .
H23B H 1.3720 0.7109 0.9891 0.072 Uiso 1 1 calc R . .
H23C H 1.4622 0.6142 0.9591 0.072 Uiso 1 1 calc R . .
O7 O 0.1958(6) -0.1140(4) -0.0026(4) 0.0866(14) Uani 1 1 d D . .
H7A H 0.229(6) -0.0416(18) 0.022(5) 0.09(2) Uiso 1 1 d D . .
H7B H 0.192(6) -0.148(4) 0.059(3) 0.08(2) Uiso 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
Cu1 0.0309(3) 0.0270(3) 0.0257(3) -0.0062(2) 0.0045(2) 0.0001(2)
Cu2 0.0322(3) 0.0283(3) 0.0290(3) -0.0081(2) 0.0017(2) -0.0013(2)
O1 0.0330(16) 0.0331(15) 0.0317(16) -0.0100(12) 0.0016(13) 0.0001(13)
O2 0.0375(16) 0.0276(15) 0.0305(15) -0.0090(12) -0.0013(13) 0.0035(13)
O3 0.0305(16) 0.0365(16) 0.0322(16) -0.0114(13) 0.0004(13) 0.0014(13)
O4 0.053(2) 0.058(2) 0.054(2) 0.0223(17) 0.0203(17) 0.0067(16)
O5 0.063(3) 0.073(3) 0.097(3) 0.015(2) -0.021(2) 0.002(2)
O6 0.084(3) 0.103(3) 0.101(3) 0.043(3) 0.043(3) -0.008(2)
N1 0.0270(18) 0.0318(18) 0.0232(17) -0.0059(14) 0.0011(14) 0.0010(14)
N2 0.0296(18) 0.0281(18) 0.0284(18) -0.0046(14) 0.0031(15) 0.0051(15)
N3 0.038(2) 0.0337(19) 0.0288(18) -0.0071(15) 0.0087(16) -0.0017(16)
N4 0.0336(19) 0.0282(18) 0.0316(19) -0.0038(15) 0.0076(16) -0.0006(15)
N5 0.0307(19) 0.0281(18) 0.0340(19) -0.0044(15) 0.0071(16) -0.0070(15)
N6 0.054(3) 0.037(2) 0.041(2) -0.0051(19) 0.010(2) -0.001(2)
C1 0.033(2) 0.032(2) 0.023(2) -0.0050(17) 0.0079(17) -0.0036(18)
C2 0.026(2) 0.032(2) 0.0183(19) -0.0023(16) 0.0036(16) -0.0010(17)
C3 0.035(2) 0.029(2) 0.028(2) -0.0037(17) 0.0080(18) -0.0006(18)
C4 0.037(2) 0.037(2) 0.037(2) 0.0063(19) 0.009(2) 0.011(2)
C5 0.029(2) 0.057(3) 0.034(2) 0.005(2) 0.0033(19) 0.010(2)
C6 0.030(2) 0.049(3) 0.027(2) -0.0057(19) 0.0008(18) -0.002(2)
C7 0.030(2) 0.028(2) 0.024(2) -0.0008(17) 0.0063(17) 0.0005(18)
C8 0.028(2) 0.030(2) 0.027(2) 0.0007(18) 0.0060(18) -0.0005(18)
C9 0.038(2) 0.034(2) 0.034(2) -0.0027(19) 0.004(2) 0.0045(19)
C10 0.044(3) 0.042(3) 0.048(3) -0.006(2) 0.009(2) 0.015(2)
C11 0.052(3) 0.030(2) 0.056(3) -0.002(2) 0.011(2) 0.007(2)
C12 0.034(2) 0.043(3) 0.034(2) -0.003(2) 0.004(2) 0.000(2)
C13 0.047(3) 0.037(3) 0.042(3) 0.003(2) 0.015(2) 0.008(2)
C14 0.048(3) 0.027(2) 0.037(2) -0.0001(19) 0.021(2) 0.001(2)
C15 0.040(3) 0.030(2) 0.037(2) -0.0058(19) 0.014(2) -0.0065(19)
C16 0.033(2) 0.027(2) 0.029(2) -0.0041(17) 0.0118(18) -0.0035(18)
C17 0.029(2) 0.028(2) 0.027(2) -0.0009(17) 0.0105(17) -0.0053(17)
C18 0.031(2) 0.032(2) 0.030(2) -0.0078(18) 0.0094(18) -0.0093(18)
C19 0.030(2) 0.040(2) 0.031(2) -0.0007(19) 0.0083(18) -0.0059(19)
C20 0.038(3) 0.041(3) 0.049(3) 0.004(2) 0.003(2) 0.006(2)
C21 0.041(3) 0.029(2) 0.045(3) -0.0025(19) 0.007(2) 0.005(2)
C22 0.057(3) 0.037(3) 0.057(3) -0.009(2) 0.026(3) 0.003(2)
C23 0.037(3) 0.053(3) 0.041(3) -0.003(2) 0.000(2) -0.003(2)
O7 0.131(4) 0.046(3) 0.061(3) -0.016(2) 0.018(3) -0.030(3)

_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 N1 1.909(3) . ?
Cu1 O1 1.943(3) . ?
Cu1 N2 1.963(3) . ?
Cu1 N3 1.963(3) . ?
Cu2 O2 1.945(3) . ?
Cu2 N5 1.966(3) . ?
Cu2 N4 1.968(3) . ?
Cu2 O3 1.974(3) . ?
Cu2 O4 2.289(3) . ?
O1 C1 1.339(4) . ?
O2 C7 1.263(4) . ?
O3 C8 1.279(4) . ?
O4 N6 1.243(4) . ?
O5 N6 1.207(5) . ?
O6 N6 1.222(5) . ?
N1 C7 1.298(5) . ?
N1 C2 1.399(5) . ?
N2 C8 1.293(4) . ?
N2 C9 1.457(5) . ?
N3 C11 1.470(5) . ?
N3 H3A 0.9000 . ?
N3 H3B 0.9000 . ?
N4 C12 1.330(5) . ?
N4 C16 1.350(5) . ?
N5 C21 1.327(5) . ?
N5 C17 1.349(4) . ?
C1 C6 1.391(5) . ?
C1 C2 1.421(5) . ?
C2 C3 1.368(5) . ?
C3 C4 1.375(5) . ?
C3 H3 0.9300 . ?
C4 C5 1.379(6) . ?
C4 H4 0.9300 . ?
C5 C6 1.373(6) . ?
C5 H5 0.9300 . ?
C6 H6 0.9300 . ?
C7 C8 1.513(5) . ?
C9 C10 1.509(5) . ?
C9 H9A 0.9700 . ?
C9 H9B 0.9700 . ?
C10 C11 1.511(6) . ?
C10 H10A 0.9700 . ?
C10 H10B 0.9700 . ?
C11 H11A 0.9700 . ?
C11 H11B 0.9700 . ?
C12 C13 1.369(5) . ?
C12 H12 0.9300 . ?
C13 C14 1.384(6) . ?
C13 H13 0.9300 . ?
C14 C15 1.381(6) . ?
C14 C22 1.492(5) . ?
C15 C16 1.368(5) . ?
C15 H15 0.9300 . ?
C16 C17 1.474(5) . ?
C17 C18 1.377(5) . ?
C18 C19 1.376(6) . ?
C18 H18 0.9300 . ?
C19 C20 1.380(5) . ?
C19 C23 1.496(5) . ?
C20 C21 1.379(6) . ?
C20 H20 0.9300 . ?
C21 H21 0.9300 . ?
C22 H22A 0.9600 . ?
C22 H22B 0.9600 . ?
C22 H22C 0.9600 . ?
C23 H23A 0.9600 . ?
C23 H23B 0.9600 . ?
C23 H23C 0.9600 . ?
O7 H7A 0.848(10) . ?
O7 H7B 0.849(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
N1 Cu1 O1 83.51(12) . . ?
N1 Cu1 N2 83.60(13) . . ?
O1 Cu1 N2 167.07(12) . . ?
N1 Cu1 N3 177.70(14) . . ?
O1 Cu1 N3 95.63(12) . . ?
N2 Cu1 N3 97.29(13) . . ?
O2 Cu2 N5 169.11(13) . . ?
O2 Cu2 N4 92.67(12) . . ?
N5 Cu2 N4 82.16(13) . . ?
O2 Cu2 O3 85.41(11) . . ?
N5 Cu2 O3 97.95(12) . . ?
N4 Cu2 O3 169.69(13) . . ?
O2 Cu2 O4 87.62(12) . . ?
N5 Cu2 O4 102.54(13) . . ?
N4 Cu2 O4 97.86(13) . . ?
O3 Cu2 O4 92.19(12) . . ?
C1 O1 Cu1 111.8(2) . . ?
C7 O2 Cu2 110.8(2) . . ?
C8 O3 Cu2 109.8(2) . . ?
N6 O4 Cu2 132.1(3) . . ?
C7 N1 C2 129.5(3) . . ?
C7 N1 Cu1 115.5(3) . . ?
C2 N1 Cu1 115.0(2) . . ?
C8 N2 C9 120.3(3) . . ?
C8 N2 Cu1 112.2(2) . . ?
C9 N2 Cu1 127.5(2) . . ?
C11 N3 Cu1 117.9(3) . . ?
C11 N3 H3A 107.8 . . ?
Cu1 N3 H3A 107.8 . . ?
C11 N3 H3B 107.8 . . ?
Cu1 N3 H3B 107.8 . . ?
H3A N3 H3B 107.2 . . ?
C12 N4 C16 118.1(4) . . ?
C12 N4 Cu2 127.0(3) . . ?
C16 N4 Cu2 114.7(3) . . ?
C21 N5 C17 118.3(3) . . ?
C21 N5 Cu2 127.5(3) . . ?
C17 N5 Cu2 114.1(3) . . ?
O5 N6 O6 120.7(5) . . ?
O5 N6 O4 120.9(4) . . ?
O6 N6 O4 118.4(4) . . ?
O1 C1 C6 123.7(3) . . ?
O1 C1 C2 118.8(3) . . ?
C6 C1 C2 117.5(4) . . ?
C3 C2 N1 128.6(3) . . ?
C3 C2 C1 120.7(4) . . ?
N1 C2 C1 110.7(3) . . ?
C2 C3 C4 120.4(4) . . ?
C2 C3 H3 119.8 . . ?
C4 C3 H3 119.8 . . ?
C3 C4 C5 119.8(4) . . ?
C3 C4 H4 120.1 . . ?
C5 C4 H4 120.1 . . ?
C6 C5 C4 120.7(4) . . ?
C6 C5 H5 119.7 . . ?
C4 C5 H5 119.7 . . ?
C5 C6 C1 120.9(4) . . ?
C5 C6 H6 119.6 . . ?
C1 C6 H6 119.6 . . ?
O2 C7 N1 129.8(4) . . ?
O2 C7 C8 117.3(3) . . ?
N1 C7 C8 112.9(3) . . ?
O3 C8 N2 127.9(3) . . ?
O3 C8 C7 116.2(3) . . ?
N2 C8 C7 115.8(3) . . ?
N2 C9 C10 110.6(3) . . ?
N2 C9 H9A 109.5 . . ?
C10 C9 H9A 109.5 . . ?
N2 C9 H9B 109.5 . . ?
C10 C9 H9B 109.5 . . ?
H9A C9 H9B 108.1 . . ?
C9 C10 C11 114.2(4) . . ?
C9 C10 H10A 108.7 . . ?
C11 C10 H10A 108.7 . . ?
C9 C10 H10B 108.7 . . ?
C11 C10 H10B 108.7 . . ?
H10A C10 H10B 107.6 . . ?
N3 C11 C10 112.8(4) . . ?
N3 C11 H11A 109.0 . . ?
C10 C11 H11A 109.0 . . ?
N3 C11 H11B 109.0 . . ?
C10 C11 H11B 109.0 . . ?
H11A C11 H11B 107.8 . . ?
N4 C12 C13 123.0(4) . . ?
N4 C12 H12 118.5 . . ?
C13 C12 H12 118.5 . . ?
C12 C13 C14 119.6(4) . . ?
C12 C13 H13 120.2 . . ?
C14 C13 H13 120.2 . . ?
C15 C14 C13 117.2(4) . . ?
C15 C14 C22 121.7(4) . . ?
C13 C14 C22 121.1(4) . . ?
C16 C15 C14 120.7(4) . . ?
C16 C15 H15 119.7 . . ?
C14 C15 H15 119.7 . . ?
N4 C16 C15 121.5(4) . . ?
N4 C16 C17 113.7(3) . . ?
C15 C16 C17 124.9(4) . . ?
N5 C17 C18 121.2(4) . . ?
N5 C17 C16 114.9(3) . . ?
C18 C17 C16 123.8(4) . . ?
C19 C18 C17 120.8(4) . . ?
C19 C18 H18 119.6 . . ?
C17 C18 H18 119.6 . . ?
C18 C19 C20 117.3(4) . . ?
C18 C19 C23 120.9(4) . . ?
C20 C19 C23 121.8(4) . . ?
C21 C20 C19 119.5(4) . . ?
C21 C20 H20 120.2 . . ?
C19 C20 H20 120.2 . . ?
N5 C21 C20 122.9(4) . . ?
N5 C21 H21 118.6 . . ?
C20 C21 H21 118.6 . . ?
C14 C22 H22A 109.5 . . ?
C14 C22 H22B 109.5 . . ?
H22A C22 H22B 109.5 . . ?
C14 C22 H22C 109.5 . . ?
H22A C22 H22C 109.5 . . ?
H22B C22 H22C 109.5 . . ?
C19 C23 H23A 109.5 . . ?
C19 C23 H23B 109.5 . . ?
H23A C23 H23B 109.5 . . ?
C19 C23 H23C 109.5 . . ?
H23A C23 H23C 109.5 . . ?
H23B C23 H23C 109.5 . . ?
H7A O7 H7B 105(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
N1 Cu1 O1 C1 -3.7(3) . . . . ?
N2 Cu1 O1 C1 -8.0(7) . . . . ?
N3 Cu1 O1 C1 174.1(3) . . . . ?
N5 Cu2 O2 C7 114.0(7) . . . . ?
N4 Cu2 O2 C7 175.3(3) . . . . ?
O3 Cu2 O2 C7 5.5(3) . . . . ?
O4 Cu2 O2 C7 -86.9(3) . . . . ?
O2 Cu2 O3 C8 -6.2(3) . . . . ?
N5 Cu2 O3 C8 -175.8(3) . . . . ?
N4 Cu2 O3 C8 -85.8(7) . . . . ?
O4 Cu2 O3 C8 81.3(3) . . . . ?
O2 Cu2 O4 N6 138.9(4) . . . . ?
N5 Cu2 O4 N6 -45.1(4) . . . . ?
N4 Cu2 O4 N6 -128.8(4) . . . . ?
O3 Cu2 O4 N6 53.5(4) . . . . ?
O1 Cu1 N1 C7 -178.8(3) . . . . ?
N2 Cu1 N1 C7 0.3(3) . . . . ?
N3 Cu1 N1 C7 113(3) . . . . ?
O1 Cu1 N1 C2 2.5(3) . . . . ?
N2 Cu1 N1 C2 -178.4(3) . . . . ?
N3 Cu1 N1 C2 -66(3) . . . . ?
N1 Cu1 N2 C8 -0.6(3) . . . . ?
O1 Cu1 N2 C8 3.6(7) . . . . ?
N3 Cu1 N2 C8 -178.5(3) . . . . ?
N1 Cu1 N2 C9 -179.6(3) . . . . ?
O1 Cu1 N2 C9 -175.4(5) . . . . ?
N3 Cu1 N2 C9 2.5(4) . . . . ?
N1 Cu1 N3 C11 -103(3) . . . . ?
O1 Cu1 N3 C11 -170.7(3) . . . . ?
N2 Cu1 N3 C11 9.8(3) . . . . ?
O2 Cu2 N4 C12 8.7(4) . . . . ?
N5 Cu2 N4 C12 179.1(4) . . . . ?
O3 Cu2 N4 C12 87.7(8) . . . . ?
O4 Cu2 N4 C12 -79.2(4) . . . . ?
O2 Cu2 N4 C16 -175.8(3) . . . . ?
N5 Cu2 N4 C16 -5.4(3) . . . . ?
O3 Cu2 N4 C16 -96.8(7) . . . . ?
O4 Cu2 N4 C16 96.3(3) . . . . ?
O2 Cu2 N5 C21 -116.7(7) . . . . ?
N4 Cu2 N5 C21 -179.0(4) . . . . ?
O3 Cu2 N5 C21 -9.4(4) . . . . ?
O4 Cu2 N5 C21 84.7(4) . . . . ?
O2 Cu2 N5 C17 67.5(8) . . . . ?
N4 Cu2 N5 C17 5.3(3) . . . . ?
O3 Cu2 N5 C17 174.9(3) . . . . ?
O4 Cu2 N5 C17 -91.1(3) . . . . ?
Cu2 O4 N6 O5 20.1(6) . . . . ?
Cu2 O4 N6 O6 -160.2(4) . . . . ?
Cu1 O1 C1 C6 -176.0(3) . . . . ?
Cu1 O1 C1 C2 4.5(4) . . . . ?
C7 N1 C2 C3 0.3(7) . . . . ?
Cu1 N1 C2 C3 178.8(3) . . . . ?
C7 N1 C2 C1 -179.3(4) . . . . ?
Cu1 N1 C2 C1 -0.8(4) . . . . ?
O1 C1 C2 C3 177.9(3) . . . . ?
C6 C1 C2 C3 -1.7(6) . . . . ?
O1 C1 C2 N1 -2.5(5) . . . . ?
C6 C1 C2 N1 177.9(3) . . . . ?
N1 C2 C3 C4 -178.5(4) . . . . ?
C1 C2 C3 C4 1.1(6) . . . . ?
C2 C3 C4 C5 0.3(6) . . . . ?
C3 C4 C5 C6 -0.9(6) . . . . ?
C4 C5 C6 C1 0.2(7) . . . . ?
O1 C1 C6 C5 -178.5(4) . . . . ?
C2 C1 C6 C5 1.0(6) . . . . ?
Cu2 O2 C7 N1 176.1(4) . . . . ?
Cu2 O2 C7 C8 -3.9(4) . . . . ?
C2 N1 C7 O2 -1.4(7) . . . . ?
Cu1 N1 C7 O2 -179.9(3) . . . . ?
C2 N1 C7 C8 178.5(4) . . . . ?
Cu1 N1 C7 C8 0.1(4) . . . . ?
Cu2 O3 C8 N2 -175.2(3) . . . . ?
Cu2 O3 C8 C7 5.7(4) . . . . ?
C9 N2 C8 O3 0.8(6) . . . . ?
Cu1 N2 C8 O3 -178.3(3) . . . . ?
C9 N2 C8 C7 179.9(3) . . . . ?
Cu1 N2 C8 C7 0.8(4) . . . . ?
O2 C7 C8 O3 -1.4(5) . . . . ?
N1 C7 C8 O3 178.7(4) . . . . ?
O2 C7 C8 N2 179.4(4) . . . . ?
N1 C7 C8 N2 -0.6(5) . . . . ?
C8 N2 C9 C10 -158.4(4) . . . . ?
Cu1 N2 C9 C10 20.6(5) . . . . ?
N2 C9 C10 C11 -60.7(5) . . . . ?
Cu1 N3 C11 C10 -45.9(5) . . . . ?
C9 C10 C11 N3 77.8(5) . . . . ?
C16 N4 C12 C13 0.9(6) . . . . ?
Cu2 N4 C12 C13 176.2(3) . . . . ?
N4 C12 C13 C14 -0.5(6) . . . . ?
C12 C13 C14 C15 -0.2(6) . . . . ?
C12 C13 C14 C22 -178.4(4) . . . . ?
C13 C14 C15 C16 0.4(6) . . . . ?
C22 C14 C15 C16 178.6(4) . . . . ?
C12 N4 C16 C15 -0.6(6) . . . . ?
Cu2 N4 C16 C15 -176.5(3) . . . . ?
C12 N4 C16 C17 -179.5(3) . . . . ?
Cu2 N4 C16 C17 4.5(4) . . . . ?
C14 C15 C16 N4 -0.1(6) . . . . ?
C14 C15 C16 C17 178.8(4) . . . . ?
C21 N5 C17 C18 -1.9(6) . . . . ?
Cu2 N5 C17 C18 174.3(3) . . . . ?
C21 N5 C17 C16 179.5(4) . . . . ?
Cu2 N5 C17 C16 -4.3(4) . . . . ?
N4 C16 C17 N5 -0.2(5) . . . . ?
C15 C16 C17 N5 -179.1(4) . . . . ?
N4 C16 C17 C18 -178.7(4) . . . . ?
C15 C16 C17 C18 2.4(6) . . . . ?
N5 C17 C18 C19 0.8(6) . . . . ?
C16 C17 C18 C19 179.3(4) . . . . ?
C17 C18 C19 C20 0.9(6) . . . . ?
C17 C18 C19 C23 -178.1(4) . . . . ?
C18 C19 C20 C21 -1.6(6) . . . . ?
C23 C19 C20 C21 177.4(4) . . . . ?
C17 N5 C21 C20 1.2(6) . . . . ?
Cu2 N5 C21 C20 -174.4(3) . . . . ?
C19 C20 C21 N5 0.6(7) . . . . ?

_diffrn_measured_fraction_theta_max 0.987
_diffrn_reflns_theta_full        26.15
_diffrn_measured_fraction_theta_full 0.987
_refine_diff_density_max         0.454
_refine_diff_density_min         -0.305
_refine_diff_density_rms         0.079


data_new
_database_code_depnum_ccdc_archive 'CCDC 857812'
#TrackingRef 'new.cif'


_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C21 H24 Cu2 N6 O8'
_chemical_formula_weight         615.54

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           Orthorhomic
_symmetry_space_group_name_H-M   Pna21

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

_cell_length_a                   23.6799(4)
_cell_length_b                   9.7018(2)
_cell_length_c                   10.27770(10)
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_volume                     2361.17(7)
_cell_formula_units_Z            4
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    ?
_cell_measurement_theta_min      ?
_cell_measurement_theta_max      ?

_exptl_crystal_description       ?
_exptl_crystal_colour            ?
_exptl_crystal_size_max          0.16
_exptl_crystal_size_mid          0.06
_exptl_crystal_size_min          0.02
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.732
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1256
_exptl_absorpt_coefficient_mu    1.862
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.7549
_exptl_absorpt_correction_T_max  0.9637
_exptl_absorpt_process_details   ?

_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  ?
_diffrn_measurement_method       ?
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            10562
_diffrn_reflns_av_R_equivalents  0.0330
_diffrn_reflns_av_sigmaI/netI    0.0571
_diffrn_reflns_limit_h_min       -30
_diffrn_reflns_limit_h_max       29
_diffrn_reflns_limit_k_min       -4
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_theta_min         1.72
_diffrn_reflns_theta_max         27.60
_reflns_number_total             4779
_reflns_number_gt                3734
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    ?
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    ?
_computing_publication_material  ?

_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
[0.00000+1.00000exp(0.16(sin\q/\l)^2^)]/
[\s^2^(Fo^2^)+0.0000+0.3484*P+(0.0325P)^2^+0.0000sin\q/\l]
where P = 0.33333Fo^2^ + 0.66667Fc^2^
;
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0.030(14)
_refine_ls_number_reflns         4779
_refine_ls_number_parameters     334
_refine_ls_number_restraints     3
_refine_ls_R_factor_all          0.0558
_refine_ls_R_factor_gt           0.0372
_refine_ls_wR_factor_ref         0.0870
_refine_ls_wR_factor_gt          0.0786
_refine_ls_goodness_of_fit_ref   1.026
_refine_ls_restrained_S_all      1.027
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
Cu1 Cu 0.35923(2) 0.30058(5) 0.13869(5) 0.03427(13) Uani 1 1 d . . .
Cu2 Cu 0.30057(2) 0.79427(4) -0.00347(5) 0.03579(14) Uani 1 1 d . . .
O1 O 0.30626(12) 0.1610(3) 0.1982(3) 0.0390(7) Uani 1 1 d . . .
O2 O 0.26329(12) 0.6221(3) 0.0431(3) 0.0369(7) Uani 1 1 d . . .
O3 O 0.37151(12) 0.6899(3) 0.0138(3) 0.0404(7) Uani 1 1 d . . .
O4 O 0.31481(13) 0.8826(3) 0.2043(3) 0.0427(7) Uani 1 1 d . . .
H4A H 0.3161 0.9749 0.2013 0.064 Uiso 1 1 d R . .
H4B H 0.3487 0.8556 0.2268 0.064 Uiso 1 1 d R . .
N1 N 0.29144(14) 0.3986(3) 0.0919(3) 0.0320(8) Uani 1 1 d . . .
N2 N 0.39733(15) 0.4688(3) 0.0735(4) 0.0387(8) Uani 1 1 d . . .
N3 N 0.42887(16) 0.2056(4) 0.1972(4) 0.0441(9) Uani 1 1 d . . .
H3A H 0.4220 0.1675 0.2754 0.053 Uiso 1 1 calc R . .
H3B H 0.4361 0.1363 0.1413 0.053 Uiso 1 1 calc R . .
N4 N 0.33182(16) 0.9627(3) -0.0807(3) 0.0355(8) Uani 1 1 d . . .
N5 N 0.22837(15) 0.8869(3) -0.0436(3) 0.0332(8) Uani 1 1 d . . .
C1 C 0.25259(18) 0.2017(4) 0.1822(4) 0.0334(9) Uani 1 1 d . . .
C2 C 0.24164(17) 0.3294(4) 0.1221(4) 0.0298(9) Uani 1 1 d . . .
C3 C 0.18634(18) 0.3726(4) 0.0982(4) 0.0381(10) Uani 1 1 d . . .
H3 H 0.1797 0.4560 0.0563 0.046 Uiso 1 1 calc R . .
C4 C 0.1416(2) 0.2918(4) 0.1366(6) 0.0443(10) Uani 1 1 d . . .
H4 H 0.1047 0.3196 0.1204 0.053 Uiso 1 1 calc R . .
C5 C 0.1526(2) 0.1675(5) 0.2003(4) 0.0417(11) Uani 1 1 d . . .
H5 H 0.1224 0.1141 0.2287 0.050 Uiso 1 1 calc R . .
C6 C 0.20668(19) 0.1219(4) 0.2220(4) 0.0387(10) Uani 1 1 d . . .
H6 H 0.2127 0.0379 0.2633 0.046 Uiso 1 1 calc R . .
C7 C 0.29957(18) 0.5273(4) 0.0611(4) 0.0321(9) Uani 1 1 d . . .
C8 C 0.36126(18) 0.5649(4) 0.0480(4) 0.0333(9) Uani 1 1 d . . .
C9 C 0.45735(19) 0.5011(5) 0.0697(6) 0.0542(13) Uani 1 1 d . . .
H9A H 0.4663 0.5671 0.1376 0.065 Uiso 1 1 calc R . .
H9B H 0.4667 0.5423 -0.0135 0.065 Uiso 1 1 calc R . .
C10 C 0.4919(2) 0.3710(6) 0.0893(5) 0.0564(14) Uani 1 1 d . . .
H10A H 0.4859 0.3115 0.0147 0.068 Uiso 1 1 calc R . .
H10B H 0.5315 0.3963 0.0900 0.068 Uiso 1 1 calc R . .
C11 C 0.4800(2) 0.2907(5) 0.2079(6) 0.0552(13) Uani 1 1 d . . .
H11A H 0.5120 0.2314 0.2262 0.066 Uiso 1 1 calc R . .
H11B H 0.4758 0.3535 0.2807 0.066 Uiso 1 1 calc R . .
C12 C 0.3866(2) 0.9909(5) -0.0993(4) 0.0461(11) Uani 1 1 d . . .
H12 H 0.4133 0.9257 -0.0748 0.055 Uiso 1 1 calc R . .
C13 C 0.4047(2) 1.1129(6) -0.1532(5) 0.0592(14) Uani 1 1 d . . .
H13 H 0.4430 1.1308 -0.1637 0.071 Uiso 1 1 calc R . .
C14 C 0.3652(3) 1.2067(5) -0.1906(5) 0.0577(15) Uani 1 1 d . . .
H14 H 0.3767 1.2892 -0.2284 0.069 Uiso 1 1 calc R . .
C15 C 0.3088(2) 1.1816(5) -0.1735(5) 0.0490(13) Uani 1 1 d . . .
H15 H 0.2819 1.2462 -0.1986 0.059 Uiso 1 1 calc R . .
C16 C 0.29259(19) 1.0571(4) -0.1176(4) 0.0345(10) Uani 1 1 d . . .
C17 C 0.23461(19) 1.0139(4) -0.0961(4) 0.0332(9) Uani 1 1 d . . .
C18 C 0.1875(2) 1.0941(4) -0.1244(4) 0.0402(11) Uani 1 1 d . . .
H18 H 0.1918 1.1820 -0.1591 0.048 Uiso 1 1 calc R . .
C19 C 0.1348(2) 1.0419(5) -0.1004(4) 0.0464(12) Uani 1 1 d . . .
H19 H 0.1030 1.0948 -0.1191 0.056 Uiso 1 1 calc R . .
C20 C 0.1284(2) 0.9119(5) -0.0490(4) 0.0443(11) Uani 1 1 d . . .
H20 H 0.0929 0.8752 -0.0321 0.053 Uiso 1 1 calc R . .
C21 C 0.1775(2) 0.8376(4) -0.0233(4) 0.0398(11) Uani 1 1 d . . .
H21 H 0.1741 0.7488 0.0098 0.048 Uiso 1 1 calc R . .
N6 N 0.53263(19) 0.9144(4) 0.0340(4) 0.0570(12) Uani 1 1 d DU . .
O5 O 0.5081(2) 1.0163(6) 0.0615(8) 0.157(3) Uani 1 1 d DU . .
O6 O 0.5202(3) 0.8057(6) 0.0824(6) 0.121(2) Uani 1 1 d . . .
O7 O 0.5736(2) 0.9175(5) -0.0372(5) 0.1128(19) Uani 1 1 d . . .
O8 O 0.42654(17) 0.8303(4) 0.2856(4) 0.0738(12) Uani 1 1 d . . .
H8A H 0.4298 0.8853 0.3529 0.111 Uiso 1 1 d R . .
H8B H 0.4599 0.8443 0.2376 0.111 Uiso 1 1 d R . .

loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_23
_atom_site_aniso_U_13
_atom_site_aniso_U_12
Cu1 0.0306(3) 0.0247(2) 0.0476(3) 0.0023(3) -0.0010(2) 0.0035(2)
Cu2 0.0350(3) 0.0237(2) 0.0486(3) 0.0074(3) -0.0013(3) 0.0017(2)
O1 0.0333(18) 0.0268(14) 0.0570(19) 0.0050(14) -0.0022(14) 0.0017(12)
O2 0.0308(16) 0.0252(14) 0.0547(18) 0.0059(12) 0.0015(13) 0.0032(12)
O3 0.0359(16) 0.0297(15) 0.0556(19) 0.0048(14) 0.0017(15) -0.0023(12)
O4 0.051(2) 0.0257(14) 0.0516(17) 0.0051(13) -0.0040(14) -0.0019(13)
N1 0.0292(19) 0.0235(16) 0.0433(19) -0.0015(14) -0.0002(15) 0.0027(14)
N2 0.032(2) 0.0268(17) 0.057(2) 0.0053(16) 0.0002(18) 0.0012(15)
N3 0.038(2) 0.039(2) 0.055(2) 0.0088(18) 0.0002(18) 0.0085(17)
N4 0.041(2) 0.0299(18) 0.0355(18) 0.0021(14) -0.0017(17) -0.0019(16)
N5 0.039(2) 0.0235(16) 0.0375(19) 0.0042(13) -0.0034(15) 0.0000(15)
C1 0.036(2) 0.028(2) 0.036(2) -0.0043(17) -0.0038(18) 0.0007(18)
C2 0.027(2) 0.0258(18) 0.036(2) -0.0053(17) -0.0010(19) -0.0026(15)
C3 0.037(3) 0.029(2) 0.049(3) -0.0044(18) -0.005(2) 0.0022(18)
C4 0.036(2) 0.048(3) 0.049(2) -0.009(3) -0.003(2) -0.001(2)
C5 0.037(3) 0.044(2) 0.044(2) -0.005(2) 0.002(2) -0.015(2)
C6 0.041(3) 0.031(2) 0.045(2) 0.0041(19) -0.003(2) -0.0065(19)
C7 0.037(3) 0.0253(19) 0.034(2) -0.0010(16) 0.0002(18) -0.0031(17)
C8 0.038(3) 0.0255(19) 0.037(2) -0.0030(17) 0.0007(17) 0.0015(17)
C9 0.033(3) 0.043(3) 0.086(4) 0.012(3) 0.008(3) 0.001(2)
C10 0.028(3) 0.062(3) 0.079(4) 0.009(3) 0.005(2) 0.006(2)
C11 0.033(3) 0.062(3) 0.071(3) 0.007(3) -0.007(3) 0.006(2)
C12 0.040(3) 0.044(3) 0.055(3) 0.003(2) -0.005(2) -0.004(2)
C13 0.053(3) 0.064(4) 0.061(3) 0.005(3) 0.003(3) -0.019(3)
C14 0.074(4) 0.041(3) 0.058(3) 0.011(2) 0.004(3) -0.025(3)
C15 0.068(4) 0.035(3) 0.044(3) 0.007(2) -0.002(2) -0.003(2)
C16 0.049(3) 0.0252(19) 0.029(2) -0.0020(16) -0.0010(19) -0.0036(18)
C17 0.046(3) 0.0227(18) 0.031(2) -0.0018(16) -0.0031(19) 0.0057(17)
C18 0.055(3) 0.029(2) 0.036(2) 0.0007(18) -0.002(2) 0.010(2)
C19 0.049(3) 0.048(3) 0.042(2) 0.000(2) -0.006(2) 0.018(2)
C20 0.037(3) 0.045(3) 0.051(3) -0.007(2) -0.003(2) 0.000(2)
C21 0.043(3) 0.0280(19) 0.048(3) 0.002(2) -0.008(2) -0.0009(19)
N6 0.050(3) 0.051(3) 0.070(3) -0.011(2) 0.000(2) -0.007(2)
O5 0.079(4) 0.114(4) 0.277(8) -0.089(5) -0.035(4) 0.047(3)
O6 0.124(5) 0.101(4) 0.137(5) 0.018(3) 0.000(4) -0.049(4)
O7 0.125(5) 0.117(4) 0.096(4) -0.035(3) 0.044(3) -0.032(3)
O8 0.061(3) 0.073(3) 0.087(3) -0.001(2) -0.002(2) -0.009(2)

_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 N1 1.927(3) . ?
Cu1 O1 1.945(3) . ?
Cu1 N2 1.982(3) . ?
Cu1 N3 1.983(4) . ?
Cu2 O2 1.949(3) . ?
Cu2 N4 1.961(3) . ?
Cu2 O3 1.969(3) . ?
Cu2 N5 1.975(4) . ?
Cu2 O4 2.326(3) . ?
O1 C1 1.341(5) . ?
O2 C7 1.272(5) . ?
O3 C8 1.286(5) . ?
O4 H4A 0.8959 . ?
O4 H4B 0.8758 . ?
N1 C7 1.302(5) . ?
N1 C2 1.392(5) . ?
N2 C8 1.291(5) . ?
N2 C9 1.456(5) . ?
N3 C11 1.470(6) . ?
N3 H3A 0.9000 . ?
N3 H3B 0.9000 . ?
N4 C12 1.339(6) . ?
N4 C16 1.358(5) . ?
N5 C21 1.312(5) . ?
N5 C17 1.353(5) . ?
C1 C6 1.396(6) . ?
C1 C2 1.409(5) . ?
C2 C3 1.396(6) . ?
C3 C4 1.375(6) . ?
C3 H3 0.9300 . ?
C4 C5 1.396(6) . ?
C4 H4 0.9300 . ?
C5 C6 1.374(6) . ?
C5 H5 0.9300 . ?
C6 H6 0.9300 . ?
C7 C8 1.512(6) . ?
C9 C10 1.517(7) . ?
C9 H9A 0.9700 . ?
C9 H9B 0.9700 . ?
C10 C11 1.474(7) . ?
C10 H10A 0.9700 . ?
C10 H10B 0.9700 . ?
C11 H11A 0.9700 . ?
C11 H11B 0.9700 . ?
C12 C13 1.375(7) . ?
C12 H12 0.9300 . ?
C13 C14 1.361(8) . ?
C13 H13 0.9300 . ?
C14 C15 1.370(7) . ?
C14 H14 0.9300 . ?
C15 C16 1.391(6) . ?
C15 H15 0.9300 . ?
C16 C17 1.452(6) . ?
C17 C18 1.391(6) . ?
C18 C19 1.370(6) . ?
C18 H18 0.9300 . ?
C19 C20 1.376(6) . ?
C19 H19 0.9300 . ?
C20 C21 1.393(6) . ?
C20 H20 0.9300 . ?
C21 H21 0.9300 . ?
N6 O5 1.181(4) . ?
N6 O6 1.203(6) . ?
N6 O7 1.215(6) . ?
O8 H8A 0.8768 . ?
O8 H8B 0.9403 . ?

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
N1 Cu1 O1 83.39(13) . . ?
N1 Cu1 N2 83.60(14) . . ?
O1 Cu1 N2 166.82(13) . . ?
N1 Cu1 N3 176.54(16) . . ?
O1 Cu1 N3 96.73(14) . . ?
N2 Cu1 N3 96.13(15) . . ?
O2 Cu2 N4 169.79(13) . . ?
O2 Cu2 O3 85.62(11) . . ?
N4 Cu2 O3 98.21(13) . . ?
O2 Cu2 N5 92.81(13) . . ?
N4 Cu2 N5 82.13(14) . . ?
O3 Cu2 N5 172.37(14) . . ?
O2 Cu2 O4 98.98(11) . . ?
N4 Cu2 O4 90.58(12) . . ?
O3 Cu2 O4 89.03(13) . . ?
N5 Cu2 O4 98.60(12) . . ?
C1 O1 Cu1 111.6(2) . . ?
C7 O2 Cu2 110.5(2) . . ?
C8 O3 Cu2 110.4(3) . . ?
Cu2 O4 H4A 110.0 . . ?
Cu2 O4 H4B 105.4 . . ?
H4A O4 H4B 106.1 . . ?
C7 N1 C2 129.9(4) . . ?
C7 N1 Cu1 114.2(3) . . ?
C2 N1 Cu1 114.3(3) . . ?
C8 N2 C9 119.0(4) . . ?
C8 N2 Cu1 111.2(3) . . ?
C9 N2 Cu1 129.1(3) . . ?
C11 N3 Cu1 116.6(3) . . ?
C11 N3 H3A 108.2 . . ?
Cu1 N3 H3A 108.2 . . ?
C11 N3 H3B 108.2 . . ?
Cu1 N3 H3B 108.2 . . ?
H3A N3 H3B 107.3 . . ?
C12 N4 C16 119.0(4) . . ?
C12 N4 Cu2 126.4(3) . . ?
C16 N4 Cu2 114.6(3) . . ?
C21 N5 C17 119.7(4) . . ?
C21 N5 Cu2 126.5(3) . . ?
C17 N5 Cu2 113.8(3) . . ?
O1 C1 C6 122.6(4) . . ?
O1 C1 C2 119.2(4) . . ?
C6 C1 C2 118.2(4) . . ?
N1 C2 C3 127.7(4) . . ?
N1 C2 C1 111.5(4) . . ?
C3 C2 C1 120.9(4) . . ?
C4 C3 C2 120.1(4) . . ?
C4 C3 H3 120.0 . . ?
C2 C3 H3 120.0 . . ?
C3 C4 C5 119.0(4) . . ?
C3 C4 H4 120.5 . . ?
C5 C4 H4 120.5 . . ?
C6 C5 C4 121.8(4) . . ?
C6 C5 H5 119.1 . . ?
C4 C5 H5 119.1 . . ?
C5 C6 C1 120.0(4) . . ?
C5 C6 H6 120.0 . . ?
C1 C6 H6 120.0 . . ?
O2 C7 N1 129.0(4) . . ?
O2 C7 C8 117.7(3) . . ?
N1 C7 C8 113.3(4) . . ?
O3 C8 N2 127.7(4) . . ?
O3 C8 C7 115.8(3) . . ?
N2 C8 C7 116.5(3) . . ?
N2 C9 C10 110.1(4) . . ?
N2 C9 H9A 109.6 . . ?
C10 C9 H9A 109.6 . . ?
N2 C9 H9B 109.6 . . ?
C10 C9 H9B 109.6 . . ?
H9A C9 H9B 108.2 . . ?
C11 C10 C9 116.5(4) . . ?
C11 C10 H10A 108.2 . . ?
C9 C10 H10A 108.2 . . ?
C11 C10 H10B 108.2 . . ?
C9 C10 H10B 108.2 . . ?
H10A C10 H10B 107.3 . . ?
N3 C11 C10 113.0(5) . . ?
N3 C11 H11A 109.0 . . ?
C10 C11 H11A 109.0 . . ?
N3 C11 H11B 109.0 . . ?
C10 C11 H11B 109.0 . . ?
H11A C11 H11B 107.8 . . ?
N4 C12 C13 122.4(5) . . ?
N4 C12 H12 118.8 . . ?
C13 C12 H12 118.8 . . ?
C14 C13 C12 118.3(5) . . ?
C14 C13 H13 120.8 . . ?
C12 C13 H13 120.8 . . ?
C13 C14 C15 121.0(5) . . ?
C13 C14 H14 119.5 . . ?
C15 C14 H14 119.5 . . ?
C14 C15 C16 118.4(5) . . ?
C14 C15 H15 120.8 . . ?
C16 C15 H15 120.8 . . ?
N4 C16 C15 120.8(4) . . ?
N4 C16 C17 114.2(3) . . ?
C15 C16 C17 125.0(4) . . ?
N5 C17 C18 120.4(4) . . ?
N5 C17 C16 115.3(4) . . ?
C18 C17 C16 124.4(4) . . ?
C19 C18 C17 119.1(4) . . ?
C19 C18 H18 120.4 . . ?
C17 C18 H18 120.4 . . ?
C18 C19 C20 120.5(4) . . ?
C18 C19 H19 119.7 . . ?
C20 C19 H19 119.7 . . ?
C19 C20 C21 117.1(4) . . ?
C19 C20 H20 121.5 . . ?
C21 C20 H20 121.5 . . ?
N5 C21 C20 123.2(4) . . ?
N5 C21 H21 118.4 . . ?
C20 C21 H21 118.4 . . ?
O5 N6 O6 121.0(7) . . ?
O5 N6 O7 121.0(6) . . ?
O6 N6 O7 117.8(6) . . ?
H8A O8 H8B 104.7 . . ?

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
N1 Cu1 O1 C1 -2.0(3) . . . . ?
N2 Cu1 O1 C1 7.2(8) . . . . ?
N3 Cu1 O1 C1 174.5(3) . . . . ?
N4 Cu2 O2 C7 112.0(8) . . . . ?
O3 Cu2 O2 C7 -0.5(3) . . . . ?
N5 Cu2 O2 C7 172.0(3) . . . . ?
O4 Cu2 O2 C7 -88.8(3) . . . . ?
O2 Cu2 O3 C8 -1.1(3) . . . . ?
N4 Cu2 O3 C8 -171.6(3) . . . . ?
N5 Cu2 O3 C8 -79.5(10) . . . . ?
O4 Cu2 O3 C8 98.0(3) . . . . ?
O1 Cu1 N1 C7 168.2(3) . . . . ?
N2 Cu1 N1 C7 -9.7(3) . . . . ?
N3 Cu1 N1 C7 76(2) . . . . ?
O1 Cu1 N1 C2 0.8(3) . . . . ?
N2 Cu1 N1 C2 -177.1(3) . . . . ?
N3 Cu1 N1 C2 -92(2) . . . . ?
N1 Cu1 N2 C8 7.8(3) . . . . ?
O1 Cu1 N2 C8 -1.3(9) . . . . ?
N3 Cu1 N2 C8 -168.7(3) . . . . ?
N1 Cu1 N2 C9 178.3(4) . . . . ?
O1 Cu1 N2 C9 169.1(6) . . . . ?
N3 Cu1 N2 C9 1.8(4) . . . . ?
N1 Cu1 N3 C11 -70(3) . . . . ?
O1 Cu1 N3 C11 -162.3(3) . . . . ?
N2 Cu1 N3 C11 14.8(4) . . . . ?
O2 Cu2 N4 C12 -117.1(8) . . . . ?
O3 Cu2 N4 C12 -5.6(4) . . . . ?
N5 Cu2 N4 C12 -177.9(4) . . . . ?
O4 Cu2 N4 C12 83.5(4) . . . . ?
O2 Cu2 N4 C16 62.9(9) . . . . ?
O3 Cu2 N4 C16 174.4(3) . . . . ?
N5 Cu2 N4 C16 2.1(3) . . . . ?
O4 Cu2 N4 C16 -96.5(3) . . . . ?
O2 Cu2 N5 C21 7.2(4) . . . . ?
N4 Cu2 N5 C21 178.3(4) . . . . ?
O3 Cu2 N5 C21 85.1(10) . . . . ?
O4 Cu2 N5 C21 -92.4(4) . . . . ?
O2 Cu2 N5 C17 -173.4(3) . . . . ?
N4 Cu2 N5 C17 -2.3(3) . . . . ?
O3 Cu2 N5 C17 -95.4(10) . . . . ?
O4 Cu2 N5 C17 87.1(3) . . . . ?
Cu1 O1 C1 C6 -177.5(3) . . . . ?
Cu1 O1 C1 C2 3.0(5) . . . . ?
C7 N1 C2 C3 16.2(7) . . . . ?
Cu1 N1 C2 C3 -178.8(3) . . . . ?
C7 N1 C2 C1 -164.5(4) . . . . ?
Cu1 N1 C2 C1 0.5(4) . . . . ?
O1 C1 C2 N1 -2.4(5) . . . . ?
C6 C1 C2 N1 178.1(4) . . . . ?
O1 C1 C2 C3 177.0(4) . . . . ?
C6 C1 C2 C3 -2.5(6) . . . . ?
N1 C2 C3 C4 -179.0(4) . . . . ?
C1 C2 C3 C4 1.8(6) . . . . ?
C2 C3 C4 C5 0.5(7) . . . . ?
C3 C4 C5 C6 -2.0(7) . . . . ?
C4 C5 C6 C1 1.2(7) . . . . ?
O1 C1 C6 C5 -178.4(4) . . . . ?
C2 C1 C6 C5 1.1(6) . . . . ?
Cu2 O2 C7 N1 -179.2(4) . . . . ?
Cu2 O2 C7 C8 1.8(4) . . . . ?
C2 N1 C7 O2 -4.6(7) . . . . ?
Cu1 N1 C7 O2 -169.7(3) . . . . ?
C2 N1 C7 C8 174.3(4) . . . . ?
Cu1 N1 C7 C8 9.3(4) . . . . ?
Cu2 O3 C8 N2 -177.0(4) . . . . ?
Cu2 O3 C8 C7 2.3(4) . . . . ?
C9 N2 C8 O3 2.7(7) . . . . ?
Cu1 N2 C8 O3 174.2(3) . . . . ?
C9 N2 C8 C7 -176.5(4) . . . . ?
Cu1 N2 C8 C7 -5.0(4) . . . . ?
O2 C7 C8 O3 -2.9(5) . . . . ?
N1 C7 C8 O3 178.0(4) . . . . ?
O2 C7 C8 N2 176.4(4) . . . . ?
N1 C7 C8 N2 -2.7(5) . . . . ?
C8 N2 C9 C10 -174.4(4) . . . . ?
Cu1 N2 C9 C10 15.8(6) . . . . ?
N2 C9 C10 C11 -55.6(6) . . . . ?
Cu1 N3 C11 C10 -51.4(5) . . . . ?
C9 C10 C11 N3 78.7(6) . . . . ?
C16 N4 C12 C13 0.7(6) . . . . ?
Cu2 N4 C12 C13 -179.3(4) . . . . ?
N4 C12 C13 C14 -1.1(8) . . . . ?
C12 C13 C14 C15 1.0(8) . . . . ?
C13 C14 C15 C16 -0.5(7) . . . . ?
C12 N4 C16 C15 -0.1(6) . . . . ?
Cu2 N4 C16 C15 179.8(3) . . . . ?
C12 N4 C16 C17 178.4(4) . . . . ?
Cu2 N4 C16 C17 -1.6(4) . . . . ?
C14 C15 C16 N4 0.1(6) . . . . ?
C14 C15 C16 C17 -178.3(4) . . . . ?
C21 N5 C17 C18 2.2(6) . . . . ?
Cu2 N5 C17 C18 -177.3(3) . . . . ?
C21 N5 C17 C16 -178.5(4) . . . . ?
Cu2 N5 C17 C16 2.0(4) . . . . ?
N4 C16 C17 N5 -0.3(5) . . . . ?
C15 C16 C17 N5 178.2(4) . . . . ?
N4 C16 C17 C18 179.0(4) . . . . ?
C15 C16 C17 C18 -2.5(6) . . . . ?
N5 C17 C18 C19 -1.1(6) . . . . ?
C16 C17 C18 C19 179.7(4) . . . . ?
C17 C18 C19 C20 0.0(6) . . . . ?
C18 C19 C20 C21 -0.1(6) . . . . ?
C17 N5 C21 C20 -2.4(6) . . . . ?
Cu2 N5 C21 C20 177.1(3) . . . . ?
C19 C20 C21 N5 1.3(7) . . . . ?

_diffrn_measured_fraction_theta_max 1.000
_diffrn_reflns_theta_full        27.60
_diffrn_measured_fraction_theta_full 1.000
_refine_diff_density_max         0.412
_refine_diff_density_min         -0.332
_refine_diff_density_rms         0.069