# Supplementary Material (ESI) for Chemical Communications
# This journal is (c) The Royal Society of Chemistry 2009

data_global
_journal_name_full               Chem.Commun.

_journal_coden_Cambridge         0182

_publ_contact_author_name        'Juyoung Yoon'
_publ_contact_author_email       JYOON@EWHA.AC.KR

_publ_section_title              
;
Pyrophosphate Selective Fluorescent Chemosensors
Based on Coumarin-DPA-Cu(II) Complexes
;
loop_
_publ_author_name
'Juyoung Yoon'
'Min Jung Kim'
'Youngmee Kim'
'Sung-Jin Kim'
'Kyung Mi Lee'
'K. M. K. Swamy'

# Attachment '737519_revised_090914_.cif'

data_CuNO3Cu
_database_code_depnum_ccdc_archive 'CCDC 737519'

_audit_creation_method           SHELXTL
_chemical_name_systematic        
;
?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C44 H42 Cu2 N10 O20'
_chemical_formula_weight         1157.96

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                   8.4488(8)
_cell_length_b                   8.4998(8)
_cell_length_c                   17.5045(16)
_cell_angle_alpha                83.423(2)
_cell_angle_beta                 81.649(2)
_cell_angle_gamma                79.468(2)
_cell_volume                     1217.8(2)
_cell_formula_units_Z            1
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    1924
_cell_measurement_theta_min      2.36
_cell_measurement_theta_max      22.79

_exptl_crystal_description       plate
_exptl_crystal_colour            blue
_exptl_crystal_size_max          0.30
_exptl_crystal_size_mid          0.10
_exptl_crystal_size_min          0.05
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.579
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             594
_exptl_absorpt_coefficient_mu    0.964
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.891
_exptl_absorpt_correction_T_max  0.953
_exptl_absorpt_process_details   '(SADABS; Bruker, 1997)'

_exptl_special_details           
;
?
;

_diffrn_ambient_temperature      293(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            6753
_diffrn_reflns_av_R_equivalents  0.0548
_diffrn_reflns_av_sigmaI/netI    0.0887
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_theta_min         2.36
_diffrn_reflns_theta_max         26.00
_reflns_number_total             4616
_reflns_number_gt                3099
_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          
;
Oxygen atoms attached to N4, N5, and N6 atoms in nitrate anions were fixed
and treated as riding with N-O = 1.25 \%A. Oxygen atoms attached to N6
were fixed geometrically and treated as riding with O...O = 2.15 \%A.
Hydrogen atoms attached to O4 atom were treated as riding with 0.93 \%A
and U~iso~(H) = 1.2U~eq~(C).
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^)+(0.0982P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         4616
_refine_ls_number_parameters     386
_refine_ls_number_restraints     14
_refine_ls_R_factor_all          0.0794
_refine_ls_R_factor_gt           0.0598
_refine_ls_wR_factor_ref         0.1771
_refine_ls_wR_factor_gt          0.1697
_refine_ls_goodness_of_fit_ref   1.009
_refine_ls_restrained_S_all      1.014
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
C2 C 0.1849(6) -0.1102(6) 0.3627(2) 0.0368(11) Uani 1 1 d . . .
C3 C 0.3515(6) -0.1955(6) 0.3356(3) 0.0395(11) Uani 1 1 d . . .
H3A H 0.4101 -0.2320 0.3799 0.047 Uiso 1 1 calc R . .
H3B H 0.3432 -0.2890 0.3105 0.047 Uiso 1 1 calc R . .
C4 C 0.6198(6) -0.1245(6) 0.2810(3) 0.0368(11) Uani 1 1 d . . .
H4A H 0.6674 -0.2015 0.2437 0.044 Uiso 1 1 calc R . .
H4B H 0.6442 -0.1719 0.3320 0.044 Uiso 1 1 calc R . .
C5 C 0.6917(6) 0.0287(6) 0.2605(2) 0.0345(10) Uani 1 1 d . . .
C6 C 0.8493(6) 0.0305(7) 0.2245(3) 0.0485(13) Uani 1 1 d . . .
H6 H 0.9157 -0.0639 0.2098 0.058 Uiso 1 1 calc R . .
C7 C 0.9057(7) 0.1766(7) 0.2109(3) 0.0529(15) Uani 1 1 d . . .
H7 H 1.0107 0.1815 0.1870 0.064 Uiso 1 1 calc R . .
C8 C 0.3997(6) -0.0969(5) 0.2009(2) 0.0329(10) Uani 1 1 d . . .
H8A H 0.4219 -0.2085 0.1896 0.040 Uiso 1 1 calc R . .
H8B H 0.2842 -0.0592 0.2006 0.040 Uiso 1 1 calc R . .
C9 C 0.4908(5) -0.0005(5) 0.1377(2) 0.0304(10) Uani 1 1 d . . .
C10 C 0.4510(6) 0.1659(5) 0.1280(2) 0.0332(10) Uani 1 1 d . . .
C12 C 0.6193(6) -0.0727(5) 0.0878(2) 0.0319(10) Uani 1 1 d . . .
C14 C 0.0245(6) 0.1375(6) 0.3871(3) 0.0428(12) Uani 1 1 d . . .
H14 H 0.0134 0.2487 0.3849 0.051 Uiso 1 1 calc R . .
C15 C 0.5345(6) 0.2555(6) 0.0702(3) 0.0409(12) Uani 1 1 d . . .
H15 H 0.5048 0.3666 0.0640 0.049 Uiso 1 1 calc R . .
C16 C 0.6615(6) 0.1795(6) 0.0222(3) 0.0429(12) Uani 1 1 d . . .
H16 H 0.7191 0.2404 -0.0157 0.052 Uiso 1 1 calc R . .
C17 C 0.7056(6) 0.0132(6) 0.0291(2) 0.0352(11) Uani 1 1 d . . .
C18 C 0.8044(7) 0.3125(7) 0.2332(3) 0.0550(15) Uani 1 1 d . . .
H18 H 0.8396 0.4112 0.2244 0.066 Uiso 1 1 calc R . .
C19 C 0.6512(7) 0.3027(6) 0.2686(3) 0.0472(13) Uani 1 1 d . . .
H19 H 0.5834 0.3959 0.2839 0.057 Uiso 1 1 calc R . .
C20 C 0.0552(7) -0.1883(6) 0.3922(3) 0.0458(13) Uani 1 1 d . . .
H20 H 0.0665 -0.2992 0.3923 0.055 Uiso 1 1 calc R . .
C21 C -0.0895(6) -0.1005(7) 0.4210(3) 0.0497(14) Uani 1 1 d . . .
H21 H -0.1758 -0.1523 0.4423 0.060 Uiso 1 1 calc R . .
C22 C -0.1069(6) 0.0639(7) 0.4186(3) 0.0489(13) Uani 1 1 d . . .
H22 H -0.2048 0.1246 0.4377 0.059 Uiso 1 1 calc R . .
C23 C 0.8375(6) -0.0761(7) -0.0187(3) 0.0426(12) Uani 1 1 d . . .
H23 H 0.8962 -0.0213 -0.0588 0.051 Uiso 1 1 calc R . .
C24 C 0.8763(6) -0.2323(7) -0.0068(3) 0.0481(13) Uani 1 1 d . . .
H24 H 0.9648 -0.2851 -0.0375 0.058 Uiso 1 1 calc R . .
C25 C 0.7844(7) -0.3269(7) 0.0534(3) 0.0519(14) Uani 1 1 d . . .
Cu1 Cu 0.37066(7) 0.13327(7) 0.31971(3) 0.0349(2) Uani 1 1 d . . .
N1 N 0.1678(5) 0.0520(5) 0.3597(2) 0.0348(9) Uani 1 1 d . . .
N2 N 0.4422(4) -0.0873(4) 0.28053(19) 0.0299(8) Uani 1 1 d . . .
N3 N 0.5949(5) 0.1618(5) 0.2821(2) 0.0364(9) Uani 1 1 d . . .
O1 O 0.3254(4) 0.2334(4) 0.17862(17) 0.0400(8) Uani 1 1 d . . .
H1 H 0.3058 0.3306 0.1671 0.060 Uiso 1 1 calc R . .
O2 O 0.6587(4) -0.2386(4) 0.09928(17) 0.0396(8) Uani 1 1 d . . .
O3 O 0.8043(6) -0.4706(5) 0.0675(3) 0.0782(14) Uani 1 1 d . . .
O4 O 0.2902(5) 0.3572(4) 0.3438(2) 0.0528(10) Uani 1 1 d D . .
H4C H 0.303(7) 0.363(7) 0.3952(10) 0.063 Uiso 1 1 d D . .
H4D H 0.245(6) 0.430(5) 0.306(2) 0.063 Uiso 1 1 d D . .
N4 N 0.503(10) 0.9800(13) 0.5062(19) 0.042(3) Uani 0.50 1 d PD A -1
O5 O 0.4556(19) 1.0735(16) 0.4504(7) 0.092(4) Uani 0.50 1 d PD A -1
O6 O 0.4700(19) 0.9771(18) 0.4391(5) 0.087(4) Uani 0.50 1 d PD A -1
O7 O 0.5147(14) 0.8359(13) 0.4940(8) 0.111(4) Uani 0.50 1 d PD A -1
N5 N 0.1432(5) 0.6085(5) 0.1867(3) 0.0661(14) Uani 1 1 d D . .
O8 O 0.0854(6) 0.5536(6) 0.2517(3) 0.0869(15) Uani 1 1 d D . .
O9 O 0.0723(7) 0.7305(6) 0.1513(3) 0.112(2) Uani 1 1 d D . .
O10 O 0.2806(6) 0.5446(6) 0.1582(4) 0.123(2) Uani 1 1 d D . .
N6 N 0.2548(7) 0.4939(8) 0.5203(3) 0.037(2) Uani 0.50 1 d PD . .
O11 O 0.3581(6) 0.5034(7) 0.4624(3) 0.0298(13) Uani 0.50 1 d PD . .
O12 O 0.1189(8) 0.4656(16) 0.5121(6) 0.177(8) Uani 0.50 1 d PD . .
O13 O 0.2923(12) 0.4923(16) 0.5863(3) 0.161(6) Uani 0.50 1 d PD . .

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
C2 0.041(3) 0.046(3) 0.023(2) -0.001(2) 0.000(2) -0.010(2)
C3 0.045(3) 0.034(3) 0.035(3) 0.005(2) 0.004(2) -0.007(2)
C4 0.033(3) 0.039(3) 0.036(3) -0.004(2) -0.005(2) 0.001(2)
C5 0.032(3) 0.048(3) 0.025(2) -0.003(2) -0.0047(19) -0.007(2)
C6 0.037(3) 0.067(4) 0.042(3) -0.008(3) -0.005(2) -0.009(3)
C7 0.042(3) 0.083(4) 0.038(3) 0.001(3) -0.003(2) -0.025(3)
C8 0.033(3) 0.036(3) 0.031(2) -0.0097(19) 0.001(2) -0.011(2)
C9 0.031(2) 0.036(3) 0.025(2) -0.0057(18) -0.0058(19) -0.0047(19)
C10 0.037(3) 0.039(3) 0.025(2) -0.0035(19) -0.010(2) -0.003(2)
C12 0.036(3) 0.037(3) 0.025(2) -0.0049(19) -0.008(2) -0.007(2)
C14 0.037(3) 0.055(3) 0.036(3) -0.012(2) 0.001(2) -0.006(2)
C15 0.048(3) 0.036(3) 0.037(3) 0.001(2) -0.004(2) -0.007(2)
C16 0.050(3) 0.046(3) 0.032(3) 0.004(2) -0.001(2) -0.016(2)
C17 0.034(3) 0.044(3) 0.028(2) -0.004(2) -0.007(2) -0.007(2)
C18 0.056(4) 0.064(4) 0.052(3) 0.004(3) -0.007(3) -0.034(3)
C19 0.046(3) 0.044(3) 0.054(3) -0.003(2) -0.009(3) -0.014(2)
C20 0.050(3) 0.054(3) 0.036(3) -0.001(2) 0.001(2) -0.022(3)
C21 0.036(3) 0.075(4) 0.041(3) -0.001(3) -0.002(2) -0.023(3)
C22 0.033(3) 0.074(4) 0.037(3) -0.005(3) 0.002(2) -0.008(3)
C23 0.037(3) 0.060(3) 0.030(2) -0.006(2) 0.001(2) -0.009(2)
C24 0.039(3) 0.060(4) 0.040(3) -0.014(3) 0.005(2) 0.002(3)
C25 0.051(3) 0.054(4) 0.044(3) -0.013(3) 0.002(3) 0.009(3)
Cu1 0.0344(4) 0.0337(4) 0.0371(4) -0.0093(2) 0.0016(2) -0.0075(2)
N1 0.031(2) 0.043(2) 0.030(2) -0.0056(17) 0.0020(17) -0.0091(17)
N2 0.029(2) 0.031(2) 0.0278(19) -0.0016(15) 0.0000(16) -0.0054(16)
N3 0.037(2) 0.042(2) 0.033(2) -0.0061(17) -0.0050(18) -0.0111(18)
O1 0.045(2) 0.0345(18) 0.0367(18) -0.0060(14) 0.0007(16) 0.0011(15)
O2 0.042(2) 0.0343(18) 0.0373(18) -0.0058(14) 0.0044(15) 0.0000(14)
O3 0.087(3) 0.043(3) 0.085(3) -0.008(2) 0.027(3) 0.009(2)
O4 0.069(3) 0.040(2) 0.051(2) -0.0150(17) -0.013(2) -0.0003(18)
N4 0.035(6) 0.061(7) 0.024(9) 0.015(9) 0.004(10) -0.007(17)
O5 0.139(11) 0.114(11) 0.033(6) 0.007(7) -0.039(7) -0.031(10)
O6 0.123(10) 0.113(10) 0.039(6) -0.027(7) -0.028(6) -0.029(9)
O7 0.108(10) 0.072(8) 0.150(12) -0.033(8) -0.026(8) 0.015(6)
N5 0.074(4) 0.039(3) 0.086(4) -0.018(3) -0.012(3) -0.005(3)
O8 0.087(4) 0.092(4) 0.076(3) -0.005(3) -0.006(3) -0.009(3)
O9 0.139(5) 0.079(4) 0.092(4) 0.001(3) -0.020(4) 0.046(3)
O10 0.095(4) 0.048(3) 0.193(6) 0.007(3) 0.049(4) 0.011(3)
N6 0.044(5) 0.018(4) 0.056(5) 0.009(4) -0.032(5) -0.006(3)
O11 0.029(3) 0.036(3) 0.022(3) 0.012(2) -0.007(3) -0.006(3)
O12 0.136(13) 0.163(14) 0.223(16) 0.120(13) -0.063(12) -0.056(11)
O13 0.123(12) 0.120(11) 0.214(16) -0.043(11) 0.021(12) 0.032(9)

_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
C2 N1 1.355(6) . ?
C2 C20 1.390(7) . ?
C2 C3 1.498(7) . ?
C3 N2 1.484(5) . ?
C3 H3A 0.9700 . ?
C3 H3B 0.9700 . ?
C4 N2 1.477(6) . ?
C4 C5 1.521(6) . ?
C4 H4A 0.9700 . ?
C4 H4B 0.9700 . ?
C5 N3 1.327(6) . ?
C5 C6 1.390(7) . ?
C6 C7 1.394(7) . ?
C6 H6 0.9300 . ?
C7 C18 1.365(8) . ?
C7 H7 0.9300 . ?
C8 C9 1.504(6) . ?
C8 N2 1.505(5) . ?
C8 H8A 0.9700 . ?
C8 H8B 0.9700 . ?
C9 C12 1.386(6) . ?
C9 C10 1.389(6) . ?
C10 O1 1.365(5) . ?
C10 C15 1.383(6) . ?
C12 C17 1.387(6) . ?
C12 O2 1.387(5) . ?
C14 N1 1.347(6) . ?
C14 C22 1.388(7) . ?
C14 H14 0.9300 . ?
C15 C16 1.372(7) . ?
C15 H15 0.9300 . ?
C16 C17 1.390(7) . ?
C16 H16 0.9300 . ?
C17 C23 1.444(7) . ?
C18 C19 1.364(7) . ?
C18 H18 0.9300 . ?
C19 N3 1.352(6) . ?
C19 H19 0.9300 . ?
C20 C21 1.371(8) . ?
C20 H20 0.9300 . ?
C21 C22 1.375(8) . ?
C21 H21 0.9300 . ?
C22 H22 0.9300 . ?
C23 C24 1.307(7) . ?
C23 H23 0.9300 . ?
C24 C25 1.469(8) . ?
C24 H24 0.9300 . ?
C25 O3 1.204(6) . ?
C25 O2 1.391(6) . ?
Cu1 N3 1.962(4) . ?
Cu1 N1 1.969(4) . ?
Cu1 O4 1.973(3) . ?
Cu1 N2 2.027(3) . ?
O1 H1 0.8200 . ?
O4 H4C 0.93(3) . ?
O4 H4D 0.93(4) . ?
N4 O6 1.249(2) . ?
N4 O7 1.251(2) . ?
N4 O5 1.251(2) . ?
O5 O6 0.847(14) . ?
O6 O7 1.478(17) . ?
N5 O9 1.246(7) . ?
N5 O8 1.245(7) . ?
N5 O10 1.247(7) . ?
N6 O13 1.2394(18) . ?
N6 O11 1.2437(18) . ?
N6 O12 1.2469(18) . ?

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 C2 C20 120.6(5) . . ?
N1 C2 C3 115.6(4) . . ?
C20 C2 C3 123.8(5) . . ?
N2 C3 C2 110.6(4) . . ?
N2 C3 H3A 109.5 . . ?
C2 C3 H3A 109.5 . . ?
N2 C3 H3B 109.5 . . ?
C2 C3 H3B 109.5 . . ?
H3A C3 H3B 108.1 . . ?
N2 C4 C5 109.6(4) . . ?
N2 C4 H4A 109.7 . . ?
C5 C4 H4A 109.7 . . ?
N2 C4 H4B 109.7 . . ?
C5 C4 H4B 109.7 . . ?
H4A C4 H4B 108.2 . . ?
N3 C5 C6 121.7(4) . . ?
N3 C5 C4 115.1(4) . . ?
C6 C5 C4 123.1(4) . . ?
C5 C6 C7 118.6(5) . . ?
C5 C6 H6 120.7 . . ?
C7 C6 H6 120.7 . . ?
C18 C7 C6 118.9(5) . . ?
C18 C7 H7 120.5 . . ?
C6 C7 H7 120.5 . . ?
C9 C8 N2 113.8(3) . . ?
C9 C8 H8A 108.8 . . ?
N2 C8 H8A 108.8 . . ?
C9 C8 H8B 108.8 . . ?
N2 C8 H8B 108.8 . . ?
H8A C8 H8B 107.7 . . ?
C12 C9 C10 117.1(4) . . ?
C12 C9 C8 121.8(4) . . ?
C10 C9 C8 121.0(4) . . ?
O1 C10 C15 122.9(4) . . ?
O1 C10 C9 115.7(4) . . ?
C15 C10 C9 121.4(4) . . ?
C9 C12 C17 123.1(4) . . ?
C9 C12 O2 116.2(4) . . ?
C17 C12 O2 120.7(4) . . ?
N1 C14 C22 121.7(5) . . ?
N1 C14 H14 119.1 . . ?
C22 C14 H14 119.1 . . ?
C16 C15 C10 119.6(5) . . ?
C16 C15 H15 120.2 . . ?
C10 C15 H15 120.2 . . ?
C15 C16 C17 121.3(4) . . ?
C15 C16 H16 119.4 . . ?
C17 C16 H16 119.4 . . ?
C12 C17 C16 117.5(4) . . ?
C12 C17 C23 117.7(4) . . ?
C16 C17 C23 124.8(4) . . ?
C19 C18 C7 119.7(5) . . ?
C19 C18 H18 120.2 . . ?
C7 C18 H18 120.2 . . ?
N3 C19 C18 122.0(5) . . ?
N3 C19 H19 119.0 . . ?
C18 C19 H19 119.0 . . ?
C21 C20 C2 119.5(5) . . ?
C21 C20 H20 120.3 . . ?
C2 C20 H20 120.3 . . ?
C20 C21 C22 120.0(5) . . ?
C20 C21 H21 120.0 . . ?
C22 C21 H21 120.0 . . ?
C21 C22 C14 118.6(5) . . ?
C21 C22 H22 120.7 . . ?
C14 C22 H22 120.7 . . ?
C24 C23 C17 121.5(5) . . ?
C24 C23 H23 119.3 . . ?
C17 C23 H23 119.3 . . ?
C23 C24 C25 122.1(5) . . ?
C23 C24 H24 119.0 . . ?
C25 C24 H24 119.0 . . ?
O3 C25 O2 116.5(5) . . ?
O3 C25 C24 128.0(5) . . ?
O2 C25 C24 115.6(5) . . ?
N3 Cu1 N1 166.81(16) . . ?
N3 Cu1 O4 96.33(16) . . ?
N1 Cu1 O4 96.21(16) . . ?
N3 Cu1 N2 84.27(15) . . ?
N1 Cu1 N2 83.86(15) . . ?
O4 Cu1 N2 172.09(14) . . ?
C14 N1 C2 119.5(4) . . ?
C14 N1 Cu1 127.4(3) . . ?
C2 N1 Cu1 113.0(3) . . ?
C4 N2 C3 113.8(4) . . ?
C4 N2 C8 110.6(3) . . ?
C3 N2 C8 107.7(3) . . ?
C4 N2 Cu1 105.9(3) . . ?
C3 N2 Cu1 105.1(3) . . ?
C8 N2 Cu1 113.7(3) . . ?
C5 N3 C19 119.1(4) . . ?
C5 N3 Cu1 114.1(3) . . ?
C19 N3 Cu1 126.4(4) . . ?
C10 O1 H1 109.5 . . ?
C12 O2 C25 122.4(4) . . ?
Cu1 O4 H4C 108(4) . . ?
Cu1 O4 H4D 118(4) . . ?
H4C O4 H4D 134(5) . . ?
O6 N4 O7 72.5(10) . . ?
O6 N4 O5 39.6(7) . . ?
O7 N4 O5 112.0(10) . . ?
O6 O5 N4 70.1(4) . . ?
O5 O6 N4 70.3(4) . . ?
O5 O6 O7 123.9(7) . . ?
N4 O6 O7 53.8(5) . . ?
N4 O7 O6 53.7(5) . . ?
O9 N5 O8 122.1(5) . . ?
O9 N5 O10 118.9(5) . . ?
O8 N5 O10 118.8(5) . . ?
O13 N6 O11 120.5(2) . . ?
O13 N6 O12 119.8(2) . . ?
O11 N6 O12 119.1(2) . . ?

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 C2 C3 N2 -25.0(6) . . . . ?
C20 C2 C3 N2 157.5(4) . . . . ?
N2 C4 C5 N3 30.8(5) . . . . ?
N2 C4 C5 C6 -151.6(4) . . . . ?
N3 C5 C6 C7 -0.1(7) . . . . ?
C4 C5 C6 C7 -177.5(4) . . . . ?
C5 C6 C7 C18 -0.1(7) . . . . ?
N2 C8 C9 C12 103.9(5) . . . . ?
N2 C8 C9 C10 -74.9(5) . . . . ?
C12 C9 C10 O1 -179.2(4) . . . . ?
C8 C9 C10 O1 -0.3(6) . . . . ?
C12 C9 C10 C15 0.9(6) . . . . ?
C8 C9 C10 C15 179.8(4) . . . . ?
C10 C9 C12 C17 -1.0(6) . . . . ?
C8 C9 C12 C17 -179.9(4) . . . . ?
C10 C9 C12 O2 179.0(4) . . . . ?
C8 C9 C12 O2 0.1(6) . . . . ?
O1 C10 C15 C16 178.9(4) . . . . ?
C9 C10 C15 C16 -1.2(7) . . . . ?
C10 C15 C16 C17 1.6(7) . . . . ?
C9 C12 C17 C16 1.4(7) . . . . ?
O2 C12 C17 C16 -178.6(4) . . . . ?
C9 C12 C17 C23 179.6(4) . . . . ?
O2 C12 C17 C23 -0.4(6) . . . . ?
C15 C16 C17 C12 -1.7(7) . . . . ?
C15 C16 C17 C23 -179.8(5) . . . . ?
C6 C7 C18 C19 0.4(8) . . . . ?
C7 C18 C19 N3 -0.4(8) . . . . ?
N1 C2 C20 C21 -2.4(7) . . . . ?
C3 C2 C20 C21 175.0(4) . . . . ?
C2 C20 C21 C22 1.9(7) . . . . ?
C20 C21 C22 C14 -0.5(7) . . . . ?
N1 C14 C22 C21 -0.5(7) . . . . ?
C12 C17 C23 C24 -0.8(7) . . . . ?
C16 C17 C23 C24 177.2(5) . . . . ?
C17 C23 C24 C25 2.6(8) . . . . ?
C23 C24 C25 O3 176.7(6) . . . . ?
C23 C24 C25 O2 -3.0(8) . . . . ?
C22 C14 N1 C2 0.0(7) . . . . ?
C22 C14 N1 Cu1 -175.5(3) . . . . ?
C20 C2 N1 C14 1.5(6) . . . . ?
C3 C2 N1 C14 -176.1(4) . . . . ?
C20 C2 N1 Cu1 177.6(3) . . . . ?
C3 C2 N1 Cu1 0.0(5) . . . . ?
N3 Cu1 N1 C14 166.6(5) . . . . ?
O4 Cu1 N1 C14 4.7(4) . . . . ?
N2 Cu1 N1 C14 -167.3(4) . . . . ?
N3 Cu1 N1 C2 -9.2(8) . . . . ?
O4 Cu1 N1 C2 -171.1(3) . . . . ?
N2 Cu1 N1 C2 16.9(3) . . . . ?
C5 C4 N2 C3 -149.8(4) . . . . ?
C5 C4 N2 C8 88.8(4) . . . . ?
C5 C4 N2 Cu1 -34.8(4) . . . . ?
C2 C3 N2 C4 151.1(4) . . . . ?
C2 C3 N2 C8 -86.0(4) . . . . ?
C2 C3 N2 Cu1 35.6(4) . . . . ?
C9 C8 N2 C4 -51.5(5) . . . . ?
C9 C8 N2 C3 -176.5(4) . . . . ?
C9 C8 N2 Cu1 67.4(4) . . . . ?
N3 Cu1 N2 C4 24.7(3) . . . . ?
N1 Cu1 N2 C4 -149.6(3) . . . . ?
O4 Cu1 N2 C4 119.5(11) . . . . ?
N3 Cu1 N2 C3 145.4(3) . . . . ?
N1 Cu1 N2 C3 -28.8(3) . . . . ?
O4 Cu1 N2 C3 -119.8(11) . . . . ?
N3 Cu1 N2 C8 -97.0(3) . . . . ?
N1 Cu1 N2 C8 88.8(3) . . . . ?
O4 Cu1 N2 C8 -2.2(12) . . . . ?
C6 C5 N3 C19 0.0(6) . . . . ?
C4 C5 N3 C19 177.6(4) . . . . ?
C6 C5 N3 Cu1 172.8(3) . . . . ?
C4 C5 N3 Cu1 -9.6(5) . . . . ?
C18 C19 N3 C5 0.2(7) . . . . ?
C18 C19 N3 Cu1 -171.6(4) . . . . ?
N1 Cu1 N3 C5 17.1(8) . . . . ?
O4 Cu1 N3 C5 179.0(3) . . . . ?
N2 Cu1 N3 C5 -9.0(3) . . . . ?
N1 Cu1 N3 C19 -170.7(6) . . . . ?
O4 Cu1 N3 C19 -8.9(4) . . . . ?
N2 Cu1 N3 C19 163.2(4) . . . . ?
C9 C12 O2 C25 179.8(4) . . . . ?
C17 C12 O2 C25 -0.2(6) . . . . ?
O3 C25 O2 C12 -178.0(5) . . . . ?
C24 C25 O2 C12 1.8(7) . . . . ?
O7 N4 O5 O6 -5(5) . . . . ?
N4 O5 O6 O7 4(5) . . . . ?
O7 N4 O6 O5 175(5) . . . . ?
O5 N4 O6 O7 -175(5) . . . . ?
O5 N4 O7 O6 3(3) . . . . ?
O5 O6 O7 N4 -5(6) . . . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
O4 H4D O8 0.930(2) 1.86(2) 2.742(6) 158(5) .
O4 H4C O11 0.930(2) 1.92(3) 2.716(6) 142(5) .
O1 H1 O10 0.82 1.78 2.593(6) 169.0 .

_diffrn_measured_fraction_theta_max 0.963
_diffrn_reflns_theta_full        26.00
_diffrn_measured_fraction_theta_full 0.963
_refine_diff_density_max         1.189
_refine_diff_density_min         -0.450
_refine_diff_density_rms         0.130


# Attachment '2-Cu.cif'

data_ym99p212121
_database_code_depnum_ccdc_archive 'CCDC 737520'

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C22 H19 Cu N5 O9'
_chemical_formula_weight         560.96

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           Orthorhombic
_symmetry_space_group_name_H-M   P2(1)2(1)2(1)

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

_cell_length_a                   8.8036(10)
_cell_length_b                   13.0269(15)
_cell_length_c                   19.063(2)
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_volume                     2186.2(4)
_cell_formula_units_Z            4
_cell_measurement_temperature    170(2)
_cell_measurement_reflns_used    2392
_cell_measurement_theta_min      2.55
_cell_measurement_theta_max      24.21

_exptl_crystal_description       plate
_exptl_crystal_colour            blue
_exptl_crystal_size_max          0.15
_exptl_crystal_size_mid          0.08
_exptl_crystal_size_min          0.02
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.704
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1148
_exptl_absorpt_coefficient_mu    1.068
_exptl_absorpt_correction_type   none
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   ?

_exptl_special_details           
;
?
;

_diffrn_ambient_temperature      170(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            12120
_diffrn_reflns_av_R_equivalents  0.0707
_diffrn_reflns_av_sigmaI/netI    0.1112
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_l_min       -23
_diffrn_reflns_limit_l_max       23
_diffrn_reflns_theta_min         1.89
_diffrn_reflns_theta_max         26.00
_reflns_number_total             4295
_reflns_number_gt                2985
_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 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^)+(0.0244P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    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   -0.006(14)
_refine_ls_number_reflns         4295
_refine_ls_number_parameters     335
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0676
_refine_ls_R_factor_gt           0.0421
_refine_ls_wR_factor_ref         0.0740
_refine_ls_wR_factor_gt          0.0698
_refine_ls_goodness_of_fit_ref   0.838
_refine_ls_restrained_S_all      0.838
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
Cu1 Cu 0.56246(6) 0.42097(4) 0.16546(3) 0.02281(13) Uani 1 1 d . . .
N1 N 0.6776(4) 0.5508(2) 0.16642(18) 0.0217(8) Uani 1 1 d . . .
N2 N 0.3950(4) 0.5072(2) 0.12448(15) 0.0203(9) Uani 1 1 d . . .
N3 N 0.4086(4) 0.3126(2) 0.16064(17) 0.0221(8) Uani 1 1 d . . .
C1 C 0.8251(5) 0.5617(3) 0.1726(2) 0.0264(10) Uani 1 1 d . . .
H1 H 0.8856 0.5021 0.1792 0.032 Uiso 1 1 calc R . .
C2 C 0.8964(5) 0.6561(3) 0.1699(2) 0.0317(11) Uani 1 1 d . . .
H2 H 1.0037 0.6618 0.1737 0.038 Uiso 1 1 calc R . .
C3 C 0.8063(5) 0.7417(3) 0.1616(2) 0.0352(11) Uani 1 1 d . . .
H3 H 0.8512 0.8080 0.1608 0.042 Uiso 1 1 calc R . .
C4 C 0.6541(5) 0.7317(3) 0.1547(2) 0.0273(10) Uani 1 1 d . . .
H4 H 0.5922 0.7907 0.1481 0.033 Uiso 1 1 calc R . .
C5 C 0.5886(5) 0.6346(3) 0.1573(2) 0.0197(9) Uani 1 1 d . . .
C6 C 0.4206(5) 0.6136(3) 0.1522(2) 0.0252(10) Uani 1 1 d . . .
H6A H 0.3735 0.6204 0.1991 0.030 Uiso 1 1 calc R . .
H6B H 0.3726 0.6644 0.1205 0.030 Uiso 1 1 calc R . .
C7 C 0.2500(4) 0.4623(3) 0.1495(2) 0.0248(11) Uani 1 1 d . . .
H7A H 0.1664 0.4811 0.1172 0.030 Uiso 1 1 calc R . .
H7B H 0.2253 0.4893 0.1967 0.030 Uiso 1 1 calc R . .
C8 C 0.2670(5) 0.3460(3) 0.1524(2) 0.0222(10) Uani 1 1 d . . .
C9 C 0.1422(5) 0.2800(3) 0.1496(2) 0.0314(12) Uani 1 1 d . . .
H9 H 0.0422 0.3059 0.1433 0.038 Uiso 1 1 calc R . .
C10 C 0.1684(6) 0.1758(3) 0.1560(2) 0.0401(13) Uani 1 1 d . . .
H10 H 0.0860 0.1288 0.1541 0.048 Uiso 1 1 calc R . .
C11 C 0.3131(6) 0.1406(3) 0.1652(2) 0.0360(11) Uani 1 1 d . . .
H11 H 0.3319 0.0691 0.1701 0.043 Uiso 1 1 calc R . .
C12 C 0.4329(6) 0.2103(3) 0.1673(2) 0.0309(10) Uani 1 1 d . . .
H12 H 0.5336 0.1857 0.1735 0.037 Uiso 1 1 calc R . .
C13 C 0.3929(4) 0.5038(3) 0.04557(18) 0.0190(10) Uani 1 1 d . . .
H13A H 0.3855 0.4313 0.0304 0.023 Uiso 1 1 calc R . .
H13B H 0.3008 0.5398 0.0287 0.023 Uiso 1 1 calc R . .
C14 C 0.5289(5) 0.5512(3) 0.01185(18) 0.0202(10) Uani 1 1 d . . .
C15 C 0.5224(5) 0.6495(3) -0.0105(2) 0.0241(11) Uani 1 1 d . . .
H15 H 0.4265 0.6830 -0.0110 0.029 Uiso 1 1 calc R . .
C16 C 0.6535(6) 0.7060(3) -0.0336(2) 0.0260(11) Uani 1 1 d . . .
C17 C 0.8001(5) 0.5505(3) -0.02064(19) 0.0198(10) Uani 1 1 d . . .
C18 C 0.9385(5) 0.5065(3) -0.02916(19) 0.0240(9) Uani 1 1 d . . .
H18 H 1.0210 0.5456 -0.0471 0.029 Uiso 1 1 calc R . .
C19 C 0.9589(5) 0.4032(3) -0.01132(19) 0.0251(10) Uani 1 1 d . . .
C20 C 0.8365(5) 0.3479(3) 0.0156(2) 0.0245(11) Uani 1 1 d . . .
H20 H 0.8507 0.2785 0.0293 0.029 Uiso 1 1 calc R . .
C21 C 0.6952(5) 0.3925(3) 0.0226(2) 0.0235(11) Uani 1 1 d . . .
H21 H 0.6127 0.3525 0.0394 0.028 Uiso 1 1 calc R . .
C22 C 0.6712(5) 0.4969(3) 0.00503(19) 0.0204(10) Uani 1 1 d . . .
O1 O 0.6565(4) 0.7974(2) -0.04822(15) 0.0324(8) Uani 1 1 d . . .
O2 O 0.7874(3) 0.6533(2) -0.03887(14) 0.0242(7) Uani 1 1 d . . .
O3 O 1.0913(4) 0.3536(2) -0.02048(15) 0.0322(8) Uani 1 1 d . . .
H3A H 1.1493 0.3895 -0.0455 0.048 Uiso 1 1 calc R . .
N11 N 0.7364(5) 0.3378(3) 0.2598(2) 0.0362(10) Uani 1 1 d . . .
O11 O 0.7357(4) 0.3339(2) 0.19312(16) 0.0347(8) Uani 1 1 d . . .
O12 O 0.6321(4) 0.3869(2) 0.28884(16) 0.0459(10) Uani 1 1 d . . .
O13 O 0.8387(5) 0.2975(3) 0.29335(19) 0.0724(13) Uani 1 1 d . . .
N21 N 0.7922(5) 0.0300(2) 0.1583(2) 0.0316(9) Uani 1 1 d . . .
O21 O 0.8141(4) 0.0678(3) 0.09820(14) 0.0492(9) Uani 1 1 d . . .
O22 O 0.9017(4) 0.0030(3) 0.19406(15) 0.0462(9) Uani 1 1 d . . .
O23 O 0.6611(4) 0.0176(2) 0.17942(17) 0.0512(10) Uani 1 1 d . . .

loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_23
_atom_site_aniso_U_13
_atom_site_aniso_U_12
Cu1 0.0235(3) 0.0206(2) 0.0243(2) 0.0013(3) -0.0018(3) 0.0006(3)
N1 0.019(2) 0.026(2) 0.0199(17) -0.0027(18) -0.0038(19) -0.0032(14)
N2 0.023(2) 0.024(2) 0.0141(17) -0.0042(15) 0.0003(15) -0.0047(15)
N3 0.028(2) 0.0210(18) 0.0176(17) 0.0058(17) -0.002(2) -0.0011(15)
C1 0.024(3) 0.029(3) 0.027(2) 0.001(2) 0.000(2) -0.0001(19)
C2 0.020(3) 0.041(3) 0.035(3) 0.001(3) 0.002(3) -0.010(2)
C3 0.050(3) 0.032(3) 0.023(2) -0.001(2) 0.006(3) -0.017(2)
C4 0.032(3) 0.024(2) 0.026(3) 0.001(2) 0.002(2) -0.002(2)
C5 0.019(3) 0.023(2) 0.017(2) -0.0044(19) -0.001(2) -0.0004(18)
C6 0.029(3) 0.027(2) 0.020(2) -0.0021(17) -0.002(2) 0.006(2)
C7 0.018(3) 0.032(2) 0.025(3) -0.0006(19) 0.004(2) -0.0027(19)
C8 0.021(3) 0.029(2) 0.017(3) 0.0029(19) -0.003(2) -0.012(2)
C9 0.029(3) 0.044(3) 0.022(3) 0.002(2) 0.002(2) -0.010(2)
C10 0.058(4) 0.041(3) 0.021(3) -0.001(2) 0.005(3) -0.028(3)
C11 0.060(4) 0.028(3) 0.020(2) 0.001(2) 0.000(3) -0.008(2)
C12 0.040(3) 0.032(2) 0.021(2) 0.002(2) -0.005(3) -0.002(2)
C13 0.020(3) 0.020(2) 0.017(2) 0.0011(18) -0.0008(18) -0.0018(17)
C14 0.027(3) 0.023(2) 0.0102(19) -0.0034(16) 0.0002(18) -0.0062(18)
C15 0.026(3) 0.024(2) 0.022(2) 0.0018(19) 0.000(2) -0.001(2)
C16 0.033(3) 0.028(3) 0.017(2) 0.001(2) 0.003(2) -0.001(2)
C17 0.026(3) 0.017(2) 0.017(2) 0.0010(17) -0.0009(19) -0.0060(18)
C18 0.025(3) 0.022(2) 0.025(2) -0.0014(17) 0.000(2) 0.001(2)
C19 0.026(3) 0.028(3) 0.021(2) -0.0026(19) -0.006(2) 0.004(2)
C20 0.029(3) 0.020(2) 0.025(2) 0.003(2) -0.002(2) 0.003(2)
C21 0.030(3) 0.023(3) 0.018(2) 0.0054(18) 0.002(2) -0.005(2)
C22 0.025(3) 0.020(2) 0.016(2) -0.0022(19) 0.003(2) 0.003(2)
O1 0.038(2) 0.0191(17) 0.0400(19) 0.0055(14) 0.0083(16) -0.0053(15)
O2 0.027(2) 0.0205(17) 0.0250(17) 0.0035(13) 0.0029(15) -0.0001(14)
O3 0.029(2) 0.0270(17) 0.0410(19) 0.0045(14) 0.0045(16) 0.0060(15)
N11 0.023(3) 0.032(2) 0.054(3) 0.023(2) -0.003(2) 0.0084(19)
O11 0.036(2) 0.034(2) 0.035(2) -0.0025(15) 0.0013(16) 0.0061(15)
O12 0.049(3) 0.050(2) 0.038(2) 0.0098(16) -0.0047(18) -0.0006(17)
O13 0.052(3) 0.078(3) 0.087(3) 0.041(2) -0.017(2) 0.014(2)
N21 0.028(3) 0.031(2) 0.036(2) -0.002(2) -0.001(2) -0.0004(18)
O21 0.046(2) 0.075(3) 0.0268(17) 0.0111(19) 0.0032(16) 0.0046(19)
O22 0.033(2) 0.060(2) 0.046(2) 0.0189(17) -0.0101(17) -0.0072(17)
O23 0.028(2) 0.070(2) 0.056(2) 0.016(2) 0.0048(19) 0.0032(18)

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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Cu1 N3 1.959(3) . ?
Cu1 N1 1.971(3) . ?
Cu1 O11 1.972(3) . ?
Cu1 N2 2.012(3) . ?
N1 C1 1.312(5) . ?
N1 C5 1.355(4) . ?
N2 C7 1.483(5) . ?
N2 C6 1.501(4) . ?
N2 C13 1.505(4) . ?
N3 C8 1.330(5) . ?
N3 C12 1.355(4) . ?
C1 C2 1.382(5) . ?
C1 H1 0.9500 . ?
C2 C3 1.377(6) . ?
C2 H2 0.9500 . ?
C3 C4 1.353(6) . ?
C3 H3 0.9500 . ?
C4 C5 1.392(5) . ?
C4 H4 0.9500 . ?
C5 C6 1.506(6) . ?
C6 H6A 0.9900 . ?
C6 H6B 0.9900 . ?
C7 C8 1.524(5) . ?
C7 H7A 0.9900 . ?
C7 H7B 0.9900 . ?
C8 C9 1.396(5) . ?
C9 C10 1.383(6) . ?
C9 H9 0.9500 . ?
C10 C11 1.365(6) . ?
C10 H10 0.9500 . ?
C11 C12 1.392(6) . ?
C11 H11 0.9500 . ?
C12 H12 0.9500 . ?
C13 C14 1.493(5) . ?
C13 H13A 0.9900 . ?
C13 H13B 0.9900 . ?
C14 C15 1.351(5) . ?
C14 C22 1.445(5) . ?
C15 C16 1.437(6) . ?
C15 H15 0.9500 . ?
C16 O1 1.223(5) . ?
C16 O2 1.368(5) . ?
C17 C18 1.356(6) . ?
C17 O2 1.388(4) . ?
C17 C22 1.419(5) . ?
C18 C19 1.400(5) . ?
C18 H18 0.9500 . ?
C19 O3 1.344(5) . ?
C19 C20 1.394(6) . ?
C20 C21 1.379(6) . ?
C20 H20 0.9500 . ?
C21 C22 1.417(5) . ?
C21 H21 0.9500 . ?
O3 H3A 0.8400 . ?
N11 O13 1.223(5) . ?
N11 O12 1.248(4) . ?
N11 O11 1.272(4) . ?
N21 O22 1.231(4) . ?
N21 O23 1.233(4) . ?
N21 O21 1.262(4) . ?

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
N3 Cu1 N1 166.95(14) . . ?
N3 Cu1 O11 97.64(13) . . ?
N1 Cu1 O11 95.33(13) . . ?
N3 Cu1 N2 82.97(13) . . ?
N1 Cu1 N2 84.34(13) . . ?
O11 Cu1 N2 172.63(12) . . ?
C1 N1 C5 119.8(3) . . ?
C1 N1 Cu1 127.1(3) . . ?
C5 N1 Cu1 113.1(3) . . ?
C7 N2 C6 112.4(3) . . ?
C7 N2 C13 107.4(3) . . ?
C6 N2 C13 112.4(3) . . ?
C7 N2 Cu1 106.6(2) . . ?
C6 N2 Cu1 105.6(2) . . ?
C13 N2 Cu1 112.4(2) . . ?
C8 N3 C12 118.8(4) . . ?
C8 N3 Cu1 114.7(3) . . ?
C12 N3 Cu1 126.5(3) . . ?
N1 C1 C2 122.9(4) . . ?
N1 C1 H1 118.6 . . ?
C2 C1 H1 118.6 . . ?
C3 C2 C1 117.6(4) . . ?
C3 C2 H2 121.2 . . ?
C1 C2 H2 121.2 . . ?
C4 C3 C2 120.3(4) . . ?
C4 C3 H3 119.9 . . ?
C2 C3 H3 119.9 . . ?
C3 C4 C5 119.6(4) . . ?
C3 C4 H4 120.2 . . ?
C5 C4 H4 120.2 . . ?
N1 C5 C4 119.8(4) . . ?
N1 C5 C6 115.5(3) . . ?
C4 C5 C6 124.7(4) . . ?
N2 C6 C5 109.7(3) . . ?
N2 C6 H6A 109.7 . . ?
C5 C6 H6A 109.7 . . ?
N2 C6 H6B 109.7 . . ?
C5 C6 H6B 109.7 . . ?
H6A C6 H6B 108.2 . . ?
N2 C7 C8 108.6(3) . . ?
N2 C7 H7A 110.0 . . ?
C8 C7 H7A 110.0 . . ?
N2 C7 H7B 110.0 . . ?
C8 C7 H7B 110.0 . . ?
H7A C7 H7B 108.3 . . ?
N3 C8 C9 122.7(4) . . ?
N3 C8 C7 115.0(3) . . ?
C9 C8 C7 122.2(4) . . ?
C10 C9 C8 118.0(4) . . ?
C10 C9 H9 121.0 . . ?
C8 C9 H9 121.0 . . ?
C11 C10 C9 119.8(4) . . ?
C11 C10 H10 120.1 . . ?
C9 C10 H10 120.1 . . ?
C10 C11 C12 119.4(4) . . ?
C10 C11 H11 120.3 . . ?
C12 C11 H11 120.3 . . ?
N3 C12 C11 121.3(5) . . ?
N3 C12 H12 119.4 . . ?
C11 C12 H12 119.4 . . ?
C14 C13 N2 114.1(3) . . ?
C14 C13 H13A 108.7 . . ?
N2 C13 H13A 108.7 . . ?
C14 C13 H13B 108.7 . . ?
N2 C13 H13B 108.7 . . ?
H13A C13 H13B 107.6 . . ?
C15 C14 C22 118.2(4) . . ?
C15 C14 C13 119.6(4) . . ?
C22 C14 C13 122.1(3) . . ?
C14 C15 C16 123.2(4) . . ?
C14 C15 H15 118.4 . . ?
C16 C15 H15 118.4 . . ?
O1 C16 O2 116.9(4) . . ?
O1 C16 C15 125.8(4) . . ?
O2 C16 C15 117.3(4) . . ?
C18 C17 O2 116.7(4) . . ?
C18 C17 C22 123.5(4) . . ?
O2 C17 C22 119.8(4) . . ?
C17 C18 C19 119.5(4) . . ?
C17 C18 H18 120.2 . . ?
C19 C18 H18 120.2 . . ?
O3 C19 C20 118.0(4) . . ?
O3 C19 C18 122.8(4) . . ?
C20 C19 C18 119.1(4) . . ?
C21 C20 C19 121.0(4) . . ?
C21 C20 H20 119.5 . . ?
C19 C20 H20 119.5 . . ?
C20 C21 C22 121.1(4) . . ?
C20 C21 H21 119.5 . . ?
C22 C21 H21 119.5 . . ?
C21 C22 C17 115.8(4) . . ?
C21 C22 C14 125.3(4) . . ?
C17 C22 C14 118.9(3) . . ?
C16 O2 C17 122.3(3) . . ?
C19 O3 H3A 109.5 . . ?
O13 N11 O12 122.0(4) . . ?
O13 N11 O11 120.6(4) . . ?
O12 N11 O11 117.4(4) . . ?
N11 O11 Cu1 104.4(3) . . ?
O22 N21 O23 121.0(4) . . ?
O22 N21 O21 119.6(4) . . ?
O23 N21 O21 119.3(4) . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
N3 Cu1 N1 C1 -176.4(5) . . . . ?
O11 Cu1 N1 C1 9.6(4) . . . . ?
N2 Cu1 N1 C1 -163.0(4) . . . . ?
N3 Cu1 N1 C5 1.4(8) . . . . ?
O11 Cu1 N1 C5 -172.6(3) . . . . ?
N2 Cu1 N1 C5 14.7(3) . . . . ?
N3 Cu1 N2 C7 29.3(2) . . . . ?
N1 Cu1 N2 C7 -147.7(2) . . . . ?
N3 Cu1 N2 C6 149.0(2) . . . . ?
N3 Cu1 N2 C13 -88.1(2) . . . . ?
N1 Cu1 N2 C13 94.9(2) . . . . ?
N1 Cu1 N3 C8 -3.1(8) . . . . ?
O11 Cu1 N3 C8 170.9(3) . . . . ?
N2 Cu1 N3 C8 -16.5(3) . . . . ?
N1 Cu1 N3 C12 179.4(5) . . . . ?
O11 Cu1 N3 C12 -6.6(4) . . . . ?
N2 Cu1 N3 C12 166.0(4) . . . . ?
C5 N1 C1 C2 -0.3(7) . . . . ?
Cu1 N1 C1 C2 177.4(3) . . . . ?
N1 C1 C2 C3 1.2(7) . . . . ?
C1 C2 C3 C4 -1.6(7) . . . . ?
C2 C3 C4 C5 1.2(8) . . . . ?
C1 N1 C5 C4 -0.2(7) . . . . ?
Cu1 N1 C5 C4 -178.2(3) . . . . ?
C1 N1 C5 C6 -178.8(4) . . . . ?
Cu1 N1 C5 C6 3.2(5) . . . . ?
C3 C4 C5 N1 -0.2(7) . . . . ?
C3 C4 C5 C6 178.3(4) . . . . ?
C7 N2 C6 C5 151.8(3) . . . . ?
C13 N2 C6 C5 -86.9(4) . . . . ?
Cu1 N2 C6 C5 36.0(3) . . . . ?
N1 C5 C6 N2 -27.1(5) . . . . ?
C4 C5 C6 N2 154.4(4) . . . . ?
C6 N2 C7 C8 -151.4(3) . . . . ?
C13 N2 C7 C8 84.4(4) . . . . ?
Cu1 N2 C7 C8 -36.2(3) . . . . ?
C12 N3 C8 C9 -0.8(6) . . . . ?
Cu1 N3 C8 C9 -178.5(3) . . . . ?
C12 N3 C8 C7 176.7(4) . . . . ?
Cu1 N3 C8 C7 -1.0(5) . . . . ?
N2 C7 C8 N3 25.6(5) . . . . ?
N2 C7 C8 C9 -156.9(3) . . . . ?
N3 C8 C9 C10 0.4(6) . . . . ?
C7 C8 C9 C10 -176.9(4) . . . . ?
C8 C9 C10 C11 0.2(7) . . . . ?
C9 C10 C11 C12 -0.5(7) . . . . ?
C8 N3 C12 C11 0.4(7) . . . . ?
Cu1 N3 C12 C11 177.9(3) . . . . ?
C10 C11 C12 N3 0.2(7) . . . . ?
C7 N2 C13 C14 177.2(3) . . . . ?
C6 N2 C13 C14 53.1(4) . . . . ?
Cu1 N2 C13 C14 -65.9(4) . . . . ?
N2 C13 C14 C15 -96.2(4) . . . . ?
N2 C13 C14 C22 80.8(4) . . . . ?
C22 C14 C15 C16 -6.9(6) . . . . ?
C13 C14 C15 C16 170.2(4) . . . . ?
C14 C15 C16 O1 -173.0(4) . . . . ?
C14 C15 C16 O2 6.2(6) . . . . ?
O2 C17 C18 C19 179.6(3) . . . . ?
C22 C17 C18 C19 -0.8(6) . . . . ?
C17 C18 C19 O3 177.8(3) . . . . ?
C17 C18 C19 C20 -0.7(6) . . . . ?
O3 C19 C20 C21 -176.3(4) . . . . ?
C18 C19 C20 C21 2.2(6) . . . . ?
C19 C20 C21 C22 -2.3(6) . . . . ?
C20 C21 C22 C17 0.9(6) . . . . ?
C20 C21 C22 C14 -178.6(4) . . . . ?
C18 C17 C22 C21 0.7(6) . . . . ?
O2 C17 C22 C21 -179.7(3) . . . . ?
C18 C17 C22 C14 -179.8(4) . . . . ?
O2 C17 C22 C14 -0.2(5) . . . . ?
C15 C14 C22 C21 -176.7(4) . . . . ?
C13 C14 C22 C21 6.2(6) . . . . ?
C15 C14 C22 C17 3.8(5) . . . . ?
C13 C14 C22 C17 -173.2(3) . . . . ?
O1 C16 O2 C17 177.0(3) . . . . ?
C15 C16 O2 C17 -2.2(5) . . . . ?
C18 C17 O2 C16 179.1(3) . . . . ?
C22 C17 O2 C16 -0.5(5) . . . . ?
O13 N11 O11 Cu1 -174.3(4) . . . . ?
O12 N11 O11 Cu1 3.3(4) . . . . ?
N3 Cu1 O11 N11 -92.7(3) . . . . ?
N1 Cu1 O11 N11 85.9(3) . . . . ?

_diffrn_measured_fraction_theta_max 0.999
_diffrn_reflns_theta_full        26.00
_diffrn_measured_fraction_theta_full 0.999
_refine_diff_density_max         0.403
_refine_diff_density_min         -1.004
_refine_diff_density_rms         0.129