# Electronic Supplementary Material (ESI) for ChemComm.
# This journal is © The Royal Society of Chemistry 2014

#######################################################################
#
#                 Cambridge Crystallographic Data Centre
#                                CCDC 
# 
#######################################################################
# 
#  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.
#
#  This CIF is provided on the understanding that it is used for bona
#  fide research purposes only. It may contain copyright material
#  of the CCDC or of third parties, and may not be copied or further
#  disseminated in any form, whether machine-readable or not,
#  except for the purpose of generating routine backup copies
#  on your local computer system.
# 
#  For further information on the CCDC, data deposition and
#  data retrieval see:
#                         www.ccdc.cam.ac.uk
#
#  Bona fide researchers may freely download Mercury and enCIFer
#  from this site to visualise CIF-encoded structures and 
#  to carry out CIF format checking respectively.
#
data_1

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C23.20 H20.80 Cu2 N6.40 O8.40'
_chemical_formula_weight         650.74

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

_symmetry_cell_setting           Monoclinic
_symmetry_space_group_name_H-M   C2/c

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

_cell_length_a                   24.119(2)
_cell_length_b                   10.2056(7)
_cell_length_c                   10.8193(7)
_cell_angle_alpha                90.00
_cell_angle_beta                 91.640(6)
_cell_angle_gamma                90.00
_cell_volume                     2662.0(3)
_cell_formula_units_Z            4
_cell_measurement_temperature    123(2)
_cell_measurement_reflns_used    1485
_cell_measurement_theta_min      2.809
_cell_measurement_theta_max      22.329

_exptl_crystal_description       bar
_exptl_crystal_colour            yellow
_exptl_crystal_size_max          0.38
_exptl_crystal_size_mid          0.08
_exptl_crystal_size_min          0.07
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.624
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1320
_exptl_absorpt_coefficient_mu    1.659
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.856
_exptl_absorpt_correction_T_max  0.893
_exptl_absorpt_process_details   sadabs

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      123(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            6881
_diffrn_reflns_av_R_equivalents  0.0385
_diffrn_reflns_av_sigmaI/netI    0.0467
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_h_max       29
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_theta_min         1.69
_diffrn_reflns_theta_max         25.50
_reflns_number_total             2467
_reflns_number_gt                1781
_reflns_threshold_expression     >2sigma(I)

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

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

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.1638P)²+8.2954P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         2467
_refine_ls_number_parameters     200
_refine_ls_number_restraints     35
_refine_ls_R_factor_all          0.1142
_refine_ls_R_factor_gt           0.0920
_refine_ls_wR_factor_ref         0.2788
_refine_ls_wR_factor_gt          0.2582
_refine_ls_goodness_of_fit_ref   1.127
_refine_ls_restrained_S_all      1.130
_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 0.7602(3) 0.7113(6) 0.7778(6) 0.0424(15) Uani 1 1 d . . .
H1 H 0.7410 0.7376 0.7063 0.051 Uiso 1 1 calc R . .
C2 C 0.8234(3) 0.7584(6) 0.9324(5) 0.0391(15) Uani 1 1 d . . .
H2 H 0.8480 0.8171 0.9704 0.047 Uiso 1 1 calc R . .
C3 C 0.8174(2) 0.6348(6) 0.9831(5) 0.0335(13) Uani 1 1 d . . .
C4 C 0.7790(3) 0.5568(6) 0.9220(6) 0.0407(15) Uani 1 1 d . . .
H4 H 0.7721 0.4741 0.9543 0.049 Uiso 1 1 calc R . .
C5 C 0.8498(3) 0.5909(6) 1.0919(5) 0.0341(13) Uani 1 1 d . . .
C6 C 0.8736(3) 0.6793(7) 1.1762(6) 0.0422(15) Uani 1 1 d . . .
H6 H 0.8668 0.7684 1.1664 0.051 Uiso 1 1 calc R . .
C7 C 0.9074(3) 0.6368(7) 1.2746(6) 0.0454(16) Uani 1 1 d . . .
H7 H 0.9233 0.6969 1.3296 0.055 Uiso 1 1 calc R . .
C8 C 0.9169(3) 0.5050(7) 1.2896(6) 0.0414(15) Uani 1 1 d . . .
C9 C 0.8935(3) 0.4197(7) 1.2096(6) 0.0452(16) Uani 1 1 d . . .
H9 H 0.9006 0.3307 1.2198 0.054 Uiso 1 1 calc R . .
C10 C 0.8594(3) 0.4599(6) 1.1127(6) 0.0401(15) Uani 1 1 d . . .
H10 H 0.8426 0.3979 1.0610 0.048 Uiso 1 1 calc R . .
C11 C 0.9829(3) 0.5426(7) 1.4546(6) 0.0453(16) Uani 1 1 d . . .
H11A H 0.9594 0.6024 1.4990 0.054 Uiso 1 1 calc R . .
H11B H 1.0071 0.5932 1.4027 0.054 Uiso 1 1 calc R . .
C12 C 0.5830(17) 0.452(5) 0.765(5) 0.165(14) Uiso 0.20 1 d PD . .
H12A H 0.5872 0.4539 0.8537 0.198 Uiso 0.20 1 d PR . .
C13 C 0.535(2) 0.381(8) 0.562(5) 0.165(14) Uiso 0.20 1 d PD . .
H13A H 0.5702 0.4061 0.5302 0.247 Uiso 0.20 1 d PR . .
H13B H 0.5276 0.2909 0.5418 0.247 Uiso 0.20 1 d PR . .
H13C H 0.5064 0.4352 0.5253 0.247 Uiso 0.20 1 d PR . .
C14 C 0.485(2) 0.358(6) 0.766(8) 0.165(14) Uiso 0.20 1 d PD . .
H14A H 0.4929 0.3588 0.8532 0.247 Uiso 0.20 1 d PR . .
H14B H 0.4517 0.4079 0.7484 0.247 Uiso 0.20 1 d PR . .
H14C H 0.4792 0.2693 0.7385 0.247 Uiso 0.20 1 d PR . .
Cu1 Cu 0.69753(4) 0.47205(9) 0.73868(9) 0.0616(5) Uani 1 1 d DU . .
N1 N 0.6437(5) 0.369(2) 1.024(2) 0.118(5) Uani 0.50 1 d PD . .
N2 N 0.7508(2) 0.5927(5) 0.8190(5) 0.0439(13) Uani 1 1 d . . .
N3 N 0.7949(2) 0.7960(5) 0.8300(5) 0.0415(13) Uani 1 1 d . . .
N4 N 0.5370(12) 0.400(3) 0.701(5) 0.165(14) Uiso 0.20 1 d PD . .
N1' N 0.6493(8) 0.406(2) 1.0007(12) 0.118(5) Uani 0.50 1 d PDU . .
O1 O 0.9508(2) 0.4552(5) 1.3831(4) 0.0523(13) Uani 1 1 d . . .
O3 O 0.6377(5) 0.4451(12) 1.1083(10) 0.135(4) Uani 1 1 d D . .
O4 O 0.6921(4) 0.3417(11) 1.0110(8) 0.127(3) Uani 1 1 d D . .
O5 O 0.6201(7) 0.479(5) 0.698(6) 0.165(14) Uiso 0.20 1 d PDU . .
O2A O 0.6416(7) 0.4629(14) 0.9002(13) 0.090(4) Uani 0.50 1 d PDU . .
O2B O 0.5991(4) 0.3258(10) 0.9894(9) 0.058(3) Uani 0.50 1 d PDU . .


_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 N2 1.312(9) . ?
C1 N3 1.319(8) . ?
C1 H1 0.9300 . ?
C2 N3 1.343(7) . ?
C2 C3 1.384(9) . ?
C2 H2 0.9300 . ?
C3 C4 1.376(8) . ?
C3 C5 1.464(8) . ?
C4 N2 1.340(8) . ?
C4 H4 0.9300 . ?
C5 C10 1.374(9) . ?
C5 C6 1.395(9) . ?
C6 C7 1.391(9) . ?
C6 H6 0.9300 . ?
C7 C8 1.373(10) . ?
C7 H7 0.9300 . ?
C8 C9 1.340(10) . ?
C8 O1 1.379(7) . ?
C9 C10 1.378(9) . ?
C9 H9 0.9300 . ?
C10 H10 0.9300 . ?
C11 O1 1.401(9) . ?
C11 C11 1.533(12) 5_768 ?
C11 H11A 0.9700 . ?
C11 H11B 0.9700 . ?
C12 O5 1.201(10) . ?
C12 N4 1.395(10) . ?
C12 C14 1.92(11) 2_656 ?
C12 H12A 0.9599 . ?
C13 N4 1.519(10) . ?
C13 C14 1.95(14) 2_656 ?
C13 H13A 0.9599 . ?
C13 H13B 0.9600 . ?
C13 H13C 0.9600 . ?
C14 N4 0.77(8) 2_656 ?
C14 C14 0.82(8) 2_656 ?
C14 N4 1.521(10) . ?
C14 C12 1.92(11) 2_656 ?
C14 C13 1.95(14) 2_656 ?
C14 H14A 0.9599 . ?
C14 H14B 0.9602 . ?
C14 H14C 0.9600 . ?
Cu1 O5 1.909(10) . ?
Cu1 N3 1.955(5) 4_646 ?
Cu1 N2 1.965(5) . ?
Cu1 O3 2.160(11) 6_565 ?
Cu1 O2A 2.240(15) . ?
N1 O2B 1.210(9) . ?
N1 O3 1.211(10) . ?
N1 O4 1.212(9) . ?
N3 Cu1 1.955(5) 4_656 ?
N4 C14 0.77(8) 2_656 ?
N1' O4 1.227(10) . ?
N1' O2A 1.242(10) . ?
N1' O3 1.269(10) . ?
O3 O5 1.32(6) 6_566 ?
O3 Cu1 2.160(11) 6_566 ?
O5 O3 1.32(6) 6_565 ?
O2A H12A 1.3944 . ?

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
N2 C1 N3 124.9(6) . . ?
N2 C1 H1 117.5 . . ?
N3 C1 H1 117.5 . . ?
N3 C2 C3 122.0(6) . . ?
N3 C2 H2 119.0 . . ?
C3 C2 H2 119.0 . . ?
C4 C3 C2 114.4(5) . . ?
C4 C3 C5 123.1(5) . . ?
C2 C3 C5 122.5(6) . . ?
N2 C4 C3 124.0(6) . . ?
N2 C4 H4 118.0 . . ?
C3 C4 H4 118.0 . . ?
C10 C5 C6 117.2(5) . . ?
C10 C5 C3 120.9(5) . . ?
C6 C5 C3 121.9(5) . . ?
C7 C6 C5 121.3(6) . . ?
C7 C6 H6 119.3 . . ?
C5 C6 H6 119.3 . . ?
C8 C7 C6 119.2(6) . . ?
C8 C7 H7 120.4 . . ?
C6 C7 H7 120.4 . . ?
C9 C8 C7 119.6(6) . . ?
C9 C8 O1 117.6(6) . . ?
C7 C8 O1 122.8(6) . . ?
C8 C9 C10 121.9(6) . . ?
C8 C9 H9 119.0 . . ?
C10 C9 H9 119.0 . . ?
C5 C10 C9 120.6(6) . . ?
C5 C10 H10 119.7 . . ?
C9 C10 H10 119.7 . . ?
O1 C11 C11 105.7(7) . 5_768 ?
O1 C11 H11A 110.6 . . ?
C11 C11 H11A 110.6 5_768 . ?
O1 C11 H11B 110.6 . . ?
C11 C11 H11B 110.6 5_768 . ?
H11A C11 H11B 108.7 . . ?
O5 C12 N4 112.3(13) . . ?
O5 C12 C14 131(4) . 2_656 ?
N4 C12 C14 20(4) . 2_656 ?
O5 C12 H12A 122.8 . . ?
N4 C12 H12A 124.2 . . ?
C14 C12 H12A 104.5 2_656 . ?
N4 C13 C14 21(3) . 2_656 ?
N4 C13 H13A 108.4 . . ?
C14 C13 H13A 127.9 2_656 . ?
N4 C13 H13B 110.3 . . ?
C14 C13 H13B 93.0 2_656 . ?
H13A C13 H13B 109.5 . . ?
N4 C13 H13C 109.7 . . ?
C14 C13 H13C 105.7 2_656 . ?
H13A C13 H13C 109.5 . . ?
H13B C13 H13C 109.5 . . ?
N4 C14 C14 145(5) 2_656 2_656 ?
N4 C14 N4 130(5) 2_656 . ?
C14 C14 N4 17(3) 2_656 . ?
N4 C14 C12 38(8) 2_656 2_656 ?
C14 C14 C12 134(10) 2_656 2_656 ?
N4 C14 C12 119(3) . 2_656 ?
N4 C14 C13 46(9) 2_656 2_656 ?
C14 C14 C13 130(10) 2_656 2_656 ?
N4 C14 C13 129(4) . 2_656 ?
C12 C14 C13 83(3) 2_656 2_656 ?
N4 C14 H14A 70.3 2_656 . ?
C14 C14 H14A 104.5 2_656 . ?
N4 C14 H14A 107.6 . . ?
C12 C14 H14A 108.5 2_656 . ?
C13 C14 H14A 26.7 2_656 . ?
N4 C14 H14B 39.2 2_656 . ?
C14 C14 H14B 131.9 2_656 . ?
N4 C14 H14B 117.0 . . ?
C12 C14 H14B 2.5 2_656 . ?
C13 C14 H14B 84.2 2_656 . ?
H14A C14 H14B 109.5 . . ?
N4 C14 H14C 125.1 2_656 . ?
C14 C14 H14C 89.4 2_656 . ?
N4 C14 H14C 103.6 . . ?
C12 C14 H14C 107.9 2_656 . ?
C13 C14 H14C 111.8 2_656 . ?
H14A C14 H14C 109.5 . . ?
H14B C14 H14C 109.5 . . ?
O5 Cu1 N3 92.7(17) . 4_646 ?
O5 Cu1 N2 134.7(17) . . ?
N3 Cu1 N2 132.6(2) 4_646 . ?
O5 Cu1 O3 37.2(18) . 6_565 ?
N3 Cu1 O3 100.3(3) 4_646 6_565 ?
N2 Cu1 O3 117.4(4) . 6_565 ?
O5 Cu1 O2A 65(2) . . ?
N3 Cu1 O2A 108.8(4) 4_646 . ?
N2 Cu1 O2A 94.7(4) . . ?
O3 Cu1 O2A 96.9(5) 6_565 . ?
O2B N1 O3 110.1(13) . . ?
O2B N1 O4 137.0(15) . . ?
O3 N1 O4 111.7(12) . . ?
C1 N2 C4 116.5(5) . . ?
C1 N2 Cu1 123.0(4) . . ?
C4 N2 Cu1 120.4(4) . . ?
C1 N3 C2 118.0(5) . . ?
C1 N3 Cu1 120.3(4) . 4_656 ?
C2 N3 Cu1 121.7(4) . 4_656 ?
C14 N4 C12 121(10) 2_656 . ?
C14 N4 C13 113(10) 2_656 . ?
C12 N4 C13 123.0(8) . . ?
C14 N4 C14 18(3) 2_656 . ?
C12 N4 C14 122.4(8) . . ?
C13 N4 C14 114.6(7) . . ?
O4 N1' O2A 115.7(16) . . ?
O4 N1' O3 106.9(13) . . ?
O2A N1' O3 128.8(16) . . ?
C8 O1 C11 118.5(5) . . ?
N1 O3 N1' 22.1(18) . . ?
N1 O3 O5 167.8(15) . 6_566 ?
N1' O3 O5 160(3) . 6_566 ?
N1 O3 Cu1 130.7(10) . 6_566 ?
N1' O3 Cu1 124.2(13) . 6_566 ?
O5 O3 Cu1 61.0(7) 6_566 6_566 ?
N1 O4 N1' 22.7(18) . . ?
C12 O5 O3 147(3) . 6_565 ?
C12 O5 Cu1 126(4) . . ?
O3 O5 Cu1 81.8(16) 6_565 . ?
N1' O2A Cu1 128.7(13) . . ?
N1' O2A H12A 113.6 . . ?
Cu1 O2A H12A 107.6 . . ?

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
N3 C2 C3 C4 -1.8(9) . . . . ?
N3 C2 C3 C5 177.6(6) . . . . ?
C2 C3 C4 N2 2.7(10) . . . . ?
C5 C3 C4 N2 -176.6(6) . . . . ?
C4 C3 C5 C10 24.2(9) . . . . ?
C2 C3 C5 C10 -155.1(6) . . . . ?
C4 C3 C5 C6 -157.8(6) . . . . ?
C2 C3 C5 C6 22.9(10) . . . . ?
C10 C5 C6 C7 2.3(10) . . . . ?
C3 C5 C6 C7 -175.7(6) . . . . ?
C5 C6 C7 C8 -0.7(10) . . . . ?
C6 C7 C8 C9 -0.1(10) . . . . ?
C6 C7 C8 O1 178.5(6) . . . . ?
C7 C8 C9 C10 -0.9(11) . . . . ?
O1 C8 C9 C10 -179.6(6) . . . . ?
C6 C5 C10 C9 -3.3(10) . . . . ?
C3 C5 C10 C9 174.8(6) . . . . ?
C8 C9 C10 C5 2.7(11) . . . . ?
N3 C1 N2 C4 0.1(10) . . . . ?
N3 C1 N2 Cu1 178.8(5) . . . . ?
C3 C4 N2 C1 -1.9(10) . . . . ?
C3 C4 N2 Cu1 179.3(5) . . . . ?
O5 Cu1 N2 C1 -58(3) . . . . ?
N3 Cu1 N2 C1 122.5(5) 4_646 . . . ?
O3 Cu1 N2 C1 -16.2(7) 6_565 . . . ?
O2A Cu1 N2 C1 -116.5(7) . . . . ?
O5 Cu1 N2 C4 121(3) . . . . ?
N3 Cu1 N2 C4 -58.9(6) 4_646 . . . ?
O3 Cu1 N2 C4 162.5(6) 6_565 . . . ?
O2A Cu1 N2 C4 62.2(7) . . . . ?
N2 C1 N3 C2 0.8(10) . . . . ?
N2 C1 N3 Cu1 -177.7(5) . . . 4_656 ?
C3 C2 N3 C1 0.2(9) . . . . ?
C3 C2 N3 Cu1 178.6(5) . . . 4_656 ?
O5 C12 N4 C14 159(3) . . . 2_656 ?
O5 C12 N4 C13 0.00(19) . . . . ?
C14 C12 N4 C13 -159(3) 2_656 . . . ?
O5 C12 N4 C14 179.99(14) . . . . ?
C14 C12 N4 C14 21(3) 2_656 . . . ?
C14 C13 N4 C12 161(5) 2_656 . . . ?
C14 C13 N4 C14 -19(5) 2_656 . . . ?
N4 C14 N4 C14 161(54) 2_656 . . 2_656 ?
C12 C14 N4 C14 -154(42) 2_656 . . 2_656 ?
C13 C14 N4 C14 100(41) 2_656 . . 2_656 ?
N4 C14 N4 C12 68(15) 2_656 . . . ?
C14 C14 N4 C12 -92(39) 2_656 . . . ?
C12 C14 N4 C12 114(5) 2_656 . . . ?
C13 C14 N4 C12 7(8) 2_656 . . . ?
N4 C14 N4 C13 -112(15) 2_656 . . . ?
C14 C14 N4 C13 88(39) 2_656 . . . ?
C12 C14 N4 C13 -66(5) 2_656 . . . ?
C13 C14 N4 C13 -173(8) 2_656 . . . ?
C9 C8 O1 C11 169.3(6) . . . . ?
C7 C8 O1 C11 -9.4(10) . . . . ?
C11 C11 O1 C8 -177.8(7) 5_768 . . . ?
O2B N1 O3 N1' -113(4) . . . . ?
O4 N1 O3 N1' 78(2) . . . . ?
O2B N1 O3 O5 4(15) . . . 6_566 ?
O4 N1 O3 O5 -165(13) . . . 6_566 ?
O2B N1 O3 Cu1 165.9(11) . . . 6_566 ?
O4 N1 O3 Cu1 -4(4) . . . 6_566 ?
O4 N1' O3 N1 -70(2) . . . . ?
O2A N1' O3 N1 145(4) . . . . ?
O4 N1' O3 O5 144(4) . . . 6_566 ?
O2A N1' O3 O5 -1(7) . . . 6_566 ?
O4 N1' O3 Cu1 45(2) . . . 6_566 ?
O2A N1' O3 Cu1 -101(2) . . . 6_566 ?
O2B N1 O4 N1' 113(5) . . . . ?
O3 N1 O4 N1' -81(3) . . . . ?
O2A N1' O4 N1 -143(4) . . . . ?
O3 N1' O4 N1 66.5(18) . . . . ?
N4 C12 O5 O3 67(8) . . . 6_565 ?
C14 C12 O5 O3 77(7) 2_656 . . 6_565 ?
N4 C12 O5 Cu1 -148(4) . . . . ?
C14 C12 O5 Cu1 -139(5) 2_656 . . . ?
N3 Cu1 O5 C12 95(4) 4_646 . . . ?
N2 Cu1 O5 C12 -85(4) . . . . ?
O3 Cu1 O5 C12 -162(6) 6_565 . . . ?
O2A Cu1 O5 C12 -15(3) . . . . ?
N3 Cu1 O5 O3 -104(2) 4_646 . . 6_565 ?
N2 Cu1 O5 O3 77(4) . . . 6_565 ?
O2A Cu1 O5 O3 147(3) . . . 6_565 ?
O4 N1' O2A Cu1 -4(3) . . . . ?
O3 N1' O2A Cu1 139.7(19) . . . . ?
O5 Cu1 O2A N1' 149(3) . . . . ?
N3 Cu1 O2A N1' 65(2) 4_646 . . . ?
N2 Cu1 O2A N1' -73.1(19) . . . . ?
O3 Cu1 O2A N1' 168.5(19) 6_565 . . . ?

_diffrn_measured_fraction_theta_max 0.997
_diffrn_reflns_theta_full        25.50
_diffrn_measured_fraction_theta_full 0.997
_refine_diff_density_max         1.340
_refine_diff_density_min         -0.894
_refine_diff_density_rms         0.183
_database_code_depnum_ccdc_archive 'CCDC 984134'
#######################################################################
#
#                 Cambridge Crystallographic Data Centre
#                                CCDC 
# 
#######################################################################
# 
#  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.
#
#  This CIF is provided on the understanding that it is used for bona
#  fide research purposes only. It may contain copyright material
#  of the CCDC or of third parties, and may not be copied or further
#  disseminated in any form, whether machine-readable or not,
#  except for the purpose of generating routine backup copies
#  on your local computer system.
# 
#  For further information on the CCDC, data deposition and
#  data retrieval see:
#                         www.ccdc.cam.ac.uk
#
#  Bona fide researchers may freely download Mercury and enCIFer
#  from this site to visualise CIF-encoded structures and 
#  to carry out CIF format checking respectively.
#
data_2

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C23 H21 Cu N5 O6'
_chemical_formula_weight         526.99

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

_symmetry_cell_setting           Monoclinic
_symmetry_space_group_name_H-M   P2(1)/n

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

_cell_length_a                   8.281(3)
_cell_length_b                   15.288(6)
_cell_length_c                   18.093(7)
_cell_angle_alpha                90.00
_cell_angle_beta                 96.566(5)
_cell_angle_gamma                90.00
_cell_volume                     2275.6(16)
_cell_formula_units_Z            4
_cell_measurement_temperature    298(2)
_cell_measurement_reflns_used    3891
_cell_measurement_theta_min      2.602
_cell_measurement_theta_max      26.458

_exptl_crystal_description       block
_exptl_crystal_colour            green
_exptl_crystal_size_max          0.21
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.18
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.538
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1084
_exptl_absorpt_coefficient_mu    1.011
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.809
_exptl_absorpt_correction_T_max  0.834
_exptl_absorpt_process_details   sadabs

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      298(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            11593
_diffrn_reflns_av_R_equivalents  0.0305
_diffrn_reflns_av_sigmaI/netI    0.0419
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_theta_min         1.75
_diffrn_reflns_theta_max         25.50
_reflns_number_total             4218
_reflns_number_gt                3170
_reflns_threshold_expression     >2sigma(I)

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

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

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0765P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         4218
_refine_ls_number_parameters     317
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0574
_refine_ls_R_factor_gt           0.0411
_refine_ls_wR_factor_ref         0.1192
_refine_ls_wR_factor_gt          0.1123
_refine_ls_goodness_of_fit_ref   0.965
_refine_ls_restrained_S_all      0.965
_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 0.46190(4) 0.58560(2) 0.036811(18) 0.03455(15) Uani 1 1 d . . .
N1 N 0.5581(3) 0.64571(17) 0.13142(13) 0.0364(6) Uani 1 1 d . . .
N2 N 0.7559(3) 0.7407(2) 0.19420(14) 0.0482(7) Uani 1 1 d . . .
N3 N -0.4887(3) 0.82316(18) 0.89089(14) 0.0420(6) Uani 1 1 d . . .
N4 N -0.4496(3) 0.68821(18) 0.95490(13) 0.0393(6) Uani 1 1 d . . .
N5 N 0.1484(4) 0.6122(2) 0.06871(17) 0.0524(8) Uani 1 1 d . . .
O1 O 0.3149(2) 0.60158(14) 0.53630(11) 0.0397(5) Uani 1 1 d . . .
O2 O 0.0110(2) 0.59499(14) 0.60576(11) 0.0385(5) Uani 1 1 d . . .
O3 O 0.2503(3) 0.65343(15) 0.03262(12) 0.0456(6) Uani 1 1 d . . .
O4 O 0.0125(3) 0.6418(2) 0.0678(2) 0.1152(15) Uani 1 1 d . . .
O5 O 0.1936(3) 0.54655(18) 0.10402(16) 0.0644(7) Uani 1 1 d . . .
O6 O 0.6186(2) 0.49125(15) 0.04425(11) 0.0426(5) Uani 1 1 d . . .
C1 C 0.6829(4) 0.7008(2) 0.13369(17) 0.0430(8) Uani 1 1 d . . .
H1 H 0.7232 0.7127 0.0888 0.052 Uiso 1 1 calc R . .
C2 C 0.6978(4) 0.7209(2) 0.25761(16) 0.0453(8) Uani 1 1 d . . .
H2 H 0.7453 0.7478 0.3008 0.054 Uiso 1 1 calc R . .
C3 C 0.5707(3) 0.6627(2) 0.26380(15) 0.0347(7) Uani 1 1 d . . .
C4 C 0.5023(4) 0.6275(2) 0.19642(16) 0.0393(7) Uani 1 1 d . . .
H4 H 0.4142 0.5898 0.1965 0.047 Uiso 1 1 calc R . .
C5 C 0.5086(3) 0.6418(2) 0.33611(15) 0.0342(7) Uani 1 1 d . . .
C6 C 0.5317(4) 0.7002(2) 0.39557(15) 0.0365(7) Uani 1 1 d . . .
H6 H 0.5909 0.7512 0.3906 0.044 Uiso 1 1 calc R . .
C7 C 0.4686(4) 0.6841(2) 0.46156(15) 0.0360(7) Uani 1 1 d . . .
H7 H 0.4862 0.7239 0.5005 0.043 Uiso 1 1 calc R . .
C8 C 0.3790(3) 0.6089(2) 0.47005(15) 0.0325(7) Uani 1 1 d . . .
C9 C 0.3594(4) 0.5475(2) 0.41274(16) 0.0371(7) Uani 1 1 d . . .
H9 H 0.3043 0.4955 0.4187 0.044 Uiso 1 1 calc R . .
C10 C 0.4233(4) 0.5652(2) 0.34665(16) 0.0378(7) Uani 1 1 d . . .
H10 H 0.4087 0.5245 0.3082 0.045 Uiso 1 1 calc R . .
C11 C 0.2213(4) 0.5255(2) 0.54811(16) 0.0376(7) Uani 1 1 d . . .
H11A H 0.2902 0.4740 0.5510 0.045 Uiso 1 1 calc R . .
H11B H 0.1360 0.5179 0.5072 0.045 Uiso 1 1 calc R . .
C12 C 0.1485(4) 0.5375(2) 0.61981(16) 0.0385(7) Uani 1 1 d . . .
H12A H 0.1144 0.4815 0.6378 0.046 Uiso 1 1 calc R . .
H12B H 0.2283 0.5626 0.6573 0.046 Uiso 1 1 calc R . .
C13 C -0.0742(3) 0.6163(2) 0.66404(15) 0.0318(7) Uani 1 1 d . . .
C14 C -0.2067(4) 0.6710(2) 0.64720(15) 0.0361(7) Uani 1 1 d . . .
H14 H -0.2339 0.6898 0.5985 0.043 Uiso 1 1 calc R . .
C15 C -0.2988(4) 0.6979(2) 0.70210(15) 0.0369(7) Uani 1 1 d . . .
H15 H -0.3890 0.7334 0.6898 0.044 Uiso 1 1 calc R . .
C16 C -0.2569(3) 0.6718(2) 0.77663(15) 0.0317(7) Uani 1 1 d . . .
C17 C -0.1269(4) 0.6155(2) 0.79215(15) 0.0366(7) Uani 1 1 d . . .
H17 H -0.1001 0.5961 0.8407 0.044 Uiso 1 1 calc R . .
C18 C -0.0347(4) 0.5870(2) 0.73683(16) 0.0367(7) Uani 1 1 d . . .
H18 H 0.0520 0.5488 0.7484 0.044 Uiso 1 1 calc R . .
C19 C -0.3481(3) 0.7059(2) 0.83681(15) 0.0324(7) Uani 1 1 d . . .
C20 C -0.4106(4) 0.7902(2) 0.83648(16) 0.0389(7) Uani 1 1 d . . .
H20 H -0.3973 0.8258 0.7960 0.047 Uiso 1 1 calc R . .
C21 C -0.5021(4) 0.7697(2) 0.94759(17) 0.0399(7) Uani 1 1 d . . .
H21 H -0.5540 0.7920 0.9864 0.048 Uiso 1 1 calc R . .
C22 C -0.3716(4) 0.6564(2) 0.89943(16) 0.0377(7) Uani 1 1 d . . .
H22 H -0.3319 0.5995 0.9030 0.045 Uiso 1 1 calc R . .
C23 C 0.7394(5) 0.4703(3) 0.1020(2) 0.0650(11) Uani 1 1 d . . .
H23A H 0.6958 0.4748 0.1488 0.098 Uiso 1 1 calc R . .
H23B H 0.8289 0.5101 0.1014 0.098 Uiso 1 1 calc R . .
H23C H 0.7765 0.4116 0.0955 0.098 Uiso 1 1 calc R . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Cu1 O6 1.934(2) . ?
Cu1 O6 1.937(2) 3_665 ?
Cu1 N1 2.024(3) . ?
Cu1 O3 2.030(2) . ?
Cu1 N4 2.333(3) 1_654 ?
Cu1 Cu1 3.0356(12) 3_665 ?
N1 C1 1.330(4) . ?
N1 C4 1.341(3) . ?
N2 C2 1.328(4) . ?
N2 C1 1.336(4) . ?
N3 C21 1.326(4) . ?
N3 C20 1.337(4) . ?
N4 C21 1.321(4) . ?
N4 C22 1.345(4) . ?
N4 Cu1 2.333(3) 1_456 ?
N5 O4 1.211(4) . ?
N5 O5 1.225(4) . ?
N5 O3 1.290(3) . ?
O1 C8 1.370(3) . ?
O1 C11 1.427(4) . ?
O2 C13 1.373(3) . ?
O2 C12 1.438(3) . ?
O6 C23 1.399(4) . ?
O6 Cu1 1.937(2) 3_665 ?
C1 H1 0.9300 . ?
C2 C3 1.393(4) . ?
C2 H2 0.9300 . ?
C3 C4 1.392(4) . ?
C3 C5 1.494(4) . ?
C4 H4 0.9300 . ?
C5 C10 1.393(4) . ?
C5 C6 1.394(4) . ?
C6 C7 1.379(4) . ?
C6 H6 0.9300 . ?
C7 C8 1.386(4) . ?
C7 H7 0.9300 . ?
C8 C9 1.395(4) . ?
C9 C10 1.388(4) . ?
C9 H9 0.9300 . ?
C10 H10 0.9300 . ?
C11 C12 1.503(4) . ?
C11 H11A 0.9700 . ?
C11 H11B 0.9700 . ?
C12 H12A 0.9700 . ?
C12 H12B 0.9700 . ?
C13 C14 1.386(4) . ?
C13 C18 1.394(4) . ?
C14 C15 1.382(4) . ?
C14 H14 0.9300 . ?
C15 C16 1.411(4) . ?
C15 H15 0.9300 . ?
C16 C17 1.382(4) . ?
C16 C19 1.489(4) . ?
C17 C18 1.396(4) . ?
C17 H17 0.9300 . ?
C18 H18 0.9300 . ?
C19 C20 1.388(4) . ?
C19 C22 1.394(4) . ?
C20 H20 0.9300 . ?
C21 H21 0.9300 . ?
C22 H22 0.9300 . ?
C23 H23A 0.9600 . ?
C23 H23B 0.9600 . ?
C23 H23C 0.9600 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
O6 Cu1 O6 76.72(9) . 3_665 ?
O6 Cu1 N1 94.79(9) . . ?
O6 Cu1 N1 169.64(10) 3_665 . ?
O6 Cu1 O3 162.30(10) . . ?
O6 Cu1 O3 93.49(9) 3_665 . ?
N1 Cu1 O3 93.12(10) . . ?
O6 Cu1 N4 106.78(9) . 1_654 ?
O6 Cu1 N4 91.87(10) 3_665 1_654 ?
N1 Cu1 N4 96.32(10) . 1_654 ?
O3 Cu1 N4 88.01(9) . 1_654 ?
O6 Cu1 Cu1 38.39(6) . 3_665 ?
O6 Cu1 Cu1 38.33(6) 3_665 3_665 ?
N1 Cu1 Cu1 132.92(8) . 3_665 ?
O3 Cu1 Cu1 130.23(7) . 3_665 ?
N4 Cu1 Cu1 101.82(7) 1_654 3_665 ?
C1 N1 C4 116.7(3) . . ?
C1 N1 Cu1 122.9(2) . . ?
C4 N1 Cu1 120.4(2) . . ?
C2 N2 C1 115.5(3) . . ?
C21 N3 C20 115.3(3) . . ?
C21 N4 C22 116.5(3) . . ?
C21 N4 Cu1 125.05(19) . 1_456 ?
C22 N4 Cu1 116.4(2) . 1_456 ?
O4 N5 O5 122.8(3) . . ?
O4 N5 O3 118.1(3) . . ?
O5 N5 O3 119.1(3) . . ?
C8 O1 C11 118.0(2) . . ?
C13 O2 C12 118.4(2) . . ?
N5 O3 Cu1 110.09(19) . . ?
C23 O6 Cu1 129.7(2) . . ?
C23 O6 Cu1 125.6(2) . 3_665 ?
Cu1 O6 Cu1 103.28(9) . 3_665 ?
N1 C1 N2 126.2(3) . . ?
N1 C1 H1 116.9 . . ?
N2 C1 H1 116.9 . . ?
N2 C2 C3 124.5(3) . . ?
N2 C2 H2 117.8 . . ?
C3 C2 H2 117.8 . . ?
C4 C3 C2 114.3(3) . . ?
C4 C3 C5 122.6(3) . . ?
C2 C3 C5 123.1(3) . . ?
N1 C4 C3 122.8(3) . . ?
N1 C4 H4 118.6 . . ?
C3 C4 H4 118.6 . . ?
C10 C5 C6 117.4(3) . . ?
C10 C5 C3 122.0(3) . . ?
C6 C5 C3 120.6(3) . . ?
C7 C6 C5 121.5(3) . . ?
C7 C6 H6 119.3 . . ?
C5 C6 H6 119.3 . . ?
C6 C7 C8 120.3(3) . . ?
C6 C7 H7 119.9 . . ?
C8 C7 H7 119.9 . . ?
O1 C8 C7 115.5(2) . . ?
O1 C8 C9 124.8(3) . . ?
C7 C8 C9 119.6(3) . . ?
C10 C9 C8 119.1(3) . . ?
C10 C9 H9 120.5 . . ?
C8 C9 H9 120.5 . . ?
C9 C10 C5 122.0(3) . . ?
C9 C10 H10 119.0 . . ?
C5 C10 H10 119.0 . . ?
O1 C11 C12 108.0(2) . . ?
O1 C11 H11A 110.1 . . ?
C12 C11 H11A 110.1 . . ?
O1 C11 H11B 110.1 . . ?
C12 C11 H11B 110.1 . . ?
H11A C11 H11B 108.4 . . ?
O2 C12 C11 108.0(2) . . ?
O2 C12 H12A 110.1 . . ?
C11 C12 H12A 110.1 . . ?
O2 C12 H12B 110.1 . . ?
C11 C12 H12B 110.1 . . ?
H12A C12 H12B 108.4 . . ?
O2 C13 C14 116.0(2) . . ?
O2 C13 C18 124.3(3) . . ?
C14 C13 C18 119.7(3) . . ?
C15 C14 C13 120.7(3) . . ?
C15 C14 H14 119.7 . . ?
C13 C14 H14 119.7 . . ?
C14 C15 C16 120.5(3) . . ?
C14 C15 H15 119.8 . . ?
C16 C15 H15 119.8 . . ?
C17 C16 C15 118.1(3) . . ?
C17 C16 C19 121.2(2) . . ?
C15 C16 C19 120.7(3) . . ?
C16 C17 C18 121.7(3) . . ?
C16 C17 H17 119.1 . . ?
C18 C17 H17 119.1 . . ?
C13 C18 C17 119.2(3) . . ?
C13 C18 H18 120.4 . . ?
C17 C18 H18 120.4 . . ?
C20 C19 C22 114.9(3) . . ?
C20 C19 C16 122.8(3) . . ?
C22 C19 C16 122.3(3) . . ?
N3 C20 C19 123.9(3) . . ?
N3 C20 H20 118.0 . . ?
C19 C20 H20 118.0 . . ?
N4 C21 N3 127.1(3) . . ?
N4 C21 H21 116.5 . . ?
N3 C21 H21 116.5 . . ?
N4 C22 C19 122.3(3) . . ?
N4 C22 H22 118.9 . . ?
C19 C22 H22 118.9 . . ?
O6 C23 H23A 109.5 . . ?
O6 C23 H23B 109.5 . . ?
H23A C23 H23B 109.5 . . ?
O6 C23 H23C 109.5 . . ?
H23A C23 H23C 109.5 . . ?
H23B C23 H23C 109.5 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
O6 Cu1 N1 C1 84.0(3) . . . . ?
O6 Cu1 N1 C1 118.5(5) 3_665 . . . ?
O3 Cu1 N1 C1 -111.9(3) . . . . ?
N4 Cu1 N1 C1 -23.5(3) 1_654 . . . ?
Cu1 Cu1 N1 C1 89.1(3) 3_665 . . . ?
O6 Cu1 N1 C4 -92.5(2) . . . . ?
O6 Cu1 N1 C4 -58.0(6) 3_665 . . . ?
O3 Cu1 N1 C4 71.6(2) . . . . ?
N4 Cu1 N1 C4 160.0(2) 1_654 . . . ?
Cu1 Cu1 N1 C4 -87.4(2) 3_665 . . . ?
O4 N5 O3 Cu1 -175.8(3) . . . . ?
O5 N5 O3 Cu1 6.3(4) . . . . ?
O6 Cu1 O3 N5 27.0(4) . . . . ?
O6 Cu1 O3 N5 82.5(2) 3_665 . . . ?
N1 Cu1 O3 N5 -89.5(2) . . . . ?
N4 Cu1 O3 N5 174.2(2) 1_654 . . . ?
Cu1 Cu1 O3 N5 70.4(2) 3_665 . . . ?
O6 Cu1 O6 C23 -166.8(4) 3_665 . . . ?
N1 Cu1 O6 C23 7.2(3) . . . . ?
O3 Cu1 O6 C23 -109.1(4) . . . . ?
N4 Cu1 O6 C23 105.3(3) 1_654 . . . ?
Cu1 Cu1 O6 C23 -166.8(4) 3_665 . . . ?
O6 Cu1 O6 Cu1 0.0 3_665 . . 3_665 ?
N1 Cu1 O6 Cu1 173.99(10) . . . 3_665 ?
O3 Cu1 O6 Cu1 57.7(3) . . . 3_665 ?
N4 Cu1 O6 Cu1 -87.93(11) 1_654 . . 3_665 ?
C4 N1 C1 N2 -1.2(5) . . . . ?
Cu1 N1 C1 N2 -177.8(3) . . . . ?
C2 N2 C1 N1 1.4(5) . . . . ?
C1 N2 C2 C3 0.4(5) . . . . ?
N2 C2 C3 C4 -2.1(5) . . . . ?
N2 C2 C3 C5 179.9(3) . . . . ?
C1 N1 C4 C3 -0.9(5) . . . . ?
Cu1 N1 C4 C3 175.8(2) . . . . ?
C2 C3 C4 N1 2.4(5) . . . . ?
C5 C3 C4 N1 -179.6(3) . . . . ?
C4 C3 C5 C10 24.1(5) . . . . ?
C2 C3 C5 C10 -158.1(3) . . . . ?
C4 C3 C5 C6 -154.6(3) . . . . ?
C2 C3 C5 C6 23.3(4) . . . . ?
C10 C5 C6 C7 -1.8(4) . . . . ?
C3 C5 C6 C7 176.8(3) . . . . ?
C5 C6 C7 C8 -0.4(5) . . . . ?
C11 O1 C8 C7 180.0(3) . . . . ?
C11 O1 C8 C9 0.2(4) . . . . ?
C6 C7 C8 O1 -176.7(3) . . . . ?
C6 C7 C8 C9 3.0(5) . . . . ?
O1 C8 C9 C10 176.5(3) . . . . ?
C7 C8 C9 C10 -3.3(4) . . . . ?
C8 C9 C10 C5 1.0(5) . . . . ?
C6 C5 C10 C9 1.6(5) . . . . ?
C3 C5 C10 C9 -177.1(3) . . . . ?
C8 O1 C11 C12 -173.4(2) . . . . ?
C13 O2 C12 C11 -179.2(2) . . . . ?
O1 C11 C12 O2 78.0(3) . . . . ?
C12 O2 C13 C14 -179.2(3) . . . . ?
C12 O2 C13 C18 1.1(4) . . . . ?
O2 C13 C14 C15 -178.7(3) . . . . ?
C18 C13 C14 C15 1.0(5) . . . . ?
C13 C14 C15 C16 1.6(5) . . . . ?
C14 C15 C16 C17 -3.2(5) . . . . ?
C14 C15 C16 C19 175.4(3) . . . . ?
C15 C16 C17 C18 2.2(5) . . . . ?
C19 C16 C17 C18 -176.3(3) . . . . ?
O2 C13 C18 C17 177.7(3) . . . . ?
C14 C13 C18 C17 -2.0(5) . . . . ?
C16 C17 C18 C13 0.3(5) . . . . ?
C17 C16 C19 C20 143.7(3) . . . . ?
C15 C16 C19 C20 -34.8(4) . . . . ?
C17 C16 C19 C22 -33.6(4) . . . . ?
C15 C16 C19 C22 147.8(3) . . . . ?
C21 N3 C20 C19 0.8(4) . . . . ?
C22 C19 C20 N3 -0.4(4) . . . . ?
C16 C19 C20 N3 -177.9(3) . . . . ?
C22 N4 C21 N3 1.3(5) . . . . ?
Cu1 N4 C21 N3 -161.6(2) 1_456 . . . ?
C20 N3 C21 N4 -1.3(5) . . . . ?
C21 N4 C22 C19 -0.7(4) . . . . ?
Cu1 N4 C22 C19 163.7(2) 1_456 . . . ?
C20 C19 C22 N4 0.3(4) . . . . ?
C16 C19 C22 N4 177.9(3) . . . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
C23 H23C O3 0.96 2.51 3.093(5) 119.2 3_665
C23 H23B O4 0.96 2.63 3.562(6) 162.5 1_655
C22 H22 O5 0.93 2.52 3.439(4) 170.1 3_566
C12 H12A N3 0.97 2.66 3.531(4) 149.3 2_446
C7 H7 O4 0.93 2.38 3.279(4) 161.3 4_676
C4 H4 O5 0.93 2.42 3.144(4) 134.3 .
C1 H1 N4 0.93 2.70 3.301(4) 123.4 1_654
C23 H23C O3 0.96 2.51 3.093(5) 119.2 3_665
C23 H23B O4 0.96 2.63 3.562(6) 162.5 1_655
C22 H22 O5 0.93 2.52 3.439(4) 170.1 3_566
C12 H12A N3 0.97 2.66 3.531(4) 149.3 2_446
C7 H7 O4 0.93 2.38 3.279(4) 161.3 4_676
C4 H4 O5 0.93 2.42 3.144(4) 134.3 .
C1 H1 N4 0.93 2.70 3.301(4) 123.4 1_654

_diffrn_measured_fraction_theta_max 0.998
_diffrn_reflns_theta_full        25.50
_diffrn_measured_fraction_theta_full 0.998
_refine_diff_density_max         0.479
_refine_diff_density_min         -0.438
_refine_diff_density_rms         0.076
_database_code_depnum_ccdc_archive 'CCDC 984135'
