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


data_global
_journal_name_full               'Dalton Trans.'

_journal_coden_Cambridge         0222
_journal_volume                  ?
_journal_page_first              ?
_journal_year                    ?

_publ_contact_author_name        'Prof Dr Miaoli Zhu'
_publ_contact_author_address     
;
Institute of Molecular Science,
Shanxi University,
Taiyuan, Shanxi 030006,
Peoples Republic of China
;

_publ_contact_author_email       miaoli@sxu.edu.cn
_publ_contact_author_phone       '0086 351 701 7974'

loop_
_publ_author_name
_publ_author_address

#<--'Last name, first name'
#<--'Last name, first name'
#<--'Last name, first name'
#<--'Last name, first name'
#<--'Last name, first name'
#<--'Last name, first name'
#<--'Last name, first name'
#<--'Last name, first name'
#<--'Last name, first name'
'Ling Ma'
;
Institute of Molecular Science,
Key Laboratory of Chemical Biology and Molecular
Engineering of the Education Ministry,
Shanxi University,
Taiyuan, Shanxi 030006,
People's Republic of China
;
'Liping Lu'
;
Institute of Molecular Science,
Key Laboratory of Chemical Biology and Molecular
Engineering of the Education Ministry,
Shanxi University,
Taiyuan, Shanxi 030006,
People's Republic of China
;
'Miaoli Zhu'
;
Institute of Molecular Science,
Key Laboratory of Chemical Biology and Molecular
Engineering of the Education Ministry,
Shanxi University,
Taiyuan, Shanxi 030006,
People's Republic of China
;
'Qingming Wang'
;
Institute of Molecular Science,
Key Laboratory of Chemical Biology and Molecular
Engineering of the Education Ministry,
Shanxi University,
Taiyuan, Shanxi 030006,
People's Republic of China
;
'Ying Li'
;
Institute of Molecular Science,
Key Laboratory of Chemical Biology and Molecular
Engineering of the Education Ministry,
Shanxi University,
Taiyuan, Shanxi 030006,
People's Republic of China
;
'Shu Xing'
;
Edmond H. Fischer Signal Transduction Laboratory,
College of Life Sciences, Jilin University,
Changchun 130012, China
;
;
Xueqi Fu
;
;
Edmond H. Fischer Signal Transduction Laboratory,
College of Life Sciences, Jilin University,
Changchun 130012, China
;
'Zengqiang Gao'
;
Beijing Synchrotron Radiation Facility,
Institute of High Energy Physics,
Chinese Academy of Sciences,
Beijing 100049, People's Republic of China
;
'Yuhui Dong'
;
Beijing Synchrotron Radiation Facility,
Institute of High Energy Physics,
Chinese Academy of Sciences,
Beijing 100049, People's Republic of China
;

_publ_section_title              
;
Mononuclear complexes of copper(II) with 3,5-substituted-4-
salicylideneamino-3,5-dimethyl-1,2,4-triazole:
Synthesis, structure and potent inhibition of protein tyrosine
phosphatases
;

# Attachment '- CCDC809856-7.cif'
#==============================================================

data_I
_database_code_depnum_ccdc_archive 'CCDC 809856'
#TrackingRef '- CCDC809856-7.cif'

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C24 H28 Cu N8 O3, H2O'
_chemical_formula_sum            'C24 H30 Cu N8 O4'
_chemical_formula_weight         558.10

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                   8.2560(17)
_cell_length_b                   11.907(2)
_cell_length_c                   14.242(3)
_cell_angle_alpha                104.15(3)
_cell_angle_beta                 98.52(3)
_cell_angle_gamma                97.03(3)
_cell_volume                     1324.0(5)
_cell_formula_units_Z            2
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    ?
_cell_measurement_theta_min      0.52
_cell_measurement_theta_max      41.43

_exptl_crystal_description       block
_exptl_crystal_colour            green
_exptl_crystal_size_max          0.09
_exptl_crystal_size_mid          0.07
_exptl_crystal_size_min          0.04
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.400
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             582
_exptl_absorpt_coefficient_mu    0.870
_exptl_absorpt_correction_T_min  0.9258
_exptl_absorpt_correction_T_max  0.9660
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   sadabs

_exptl_special_details           
;
?
;

_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     0.80000
_diffrn_radiation_type           synchrotron
_diffrn_radiation_source         'synchrotron, 1W2B at BSRF'
_diffrn_radiation_monochromator  'double crystal monochromator'
_diffrn_measurement_device_type  mar555
_diffrn_measurement_method       'oscillation mode'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            3825
_diffrn_reflns_av_R_equivalents  0.0000
_diffrn_reflns_av_sigmaI/netI    0.0217
_diffrn_reflns_limit_h_min       0
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_theta_min         2.95
_diffrn_reflns_theta_max         27.40
_reflns_number_total             3825
_reflns_number_gt                3630
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       mar555
_computing_cell_refinement       'HKL 2000'
_computing_data_reduction        'HKL 2000'
_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^)+(0.1892P)^2^+0.5438P] 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     SHELXL
_refine_ls_extinction_coef       0.208(15)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^
_refine_ls_number_reflns         3825
_refine_ls_number_parameters     362
_refine_ls_number_restraints     19
_refine_ls_R_factor_all          0.0820
_refine_ls_R_factor_gt           0.0807
_refine_ls_wR_factor_ref         0.2087
_refine_ls_wR_factor_gt          0.2043
_refine_ls_goodness_of_fit_ref   1.046
_refine_ls_restrained_S_all      1.044
_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 0.67956(5) 0.74794(3) 0.71350(3) 0.0245(3) Uani 1 1 d . . .
N1 N 0.7654(4) 0.6026(2) 0.6501(2) 0.0260(7) Uani 1 1 d . . .
N2 N 0.8901(4) 0.6125(2) 0.5938(2) 0.0236(7) Uani 1 1 d . . .
N3 N 1.0165(4) 0.6519(3) 0.4788(2) 0.0281(8) Uani 1 1 d . . .
N4 N 1.1355(4) 0.6554(3) 0.5623(2) 0.0283(7) Uani 1 1 d . . .
N5 N 0.6583(4) 0.8934(2) 0.8140(2) 0.0270(7) Uani 1 1 d . . .
N6 N 0.5638(4) 0.8830(3) 0.8866(2) 0.0288(7) Uani 1 1 d . . .
N7 N 0.4855(6) 0.8273(4) 1.0089(3) 0.0599(13) Uani 1 1 d . . .
N8 N 0.3505(6) 0.8540(5) 0.9552(3) 0.0686(15) Uani 1 1 d . . .
O1 O 0.5409(3) 0.6574(2) 0.77311(19) 0.0282(6) Uani 1 1 d . . .
O2 O 0.8323(4) 0.8373(2) 0.66077(19) 0.0316(7) Uani 1 1 d . . .
C1 C 0.5488(4) 0.5533(3) 0.7866(2) 0.0271(8) Uani 1 1 d . . .
C2 C 0.4571(5) 0.5166(3) 0.8529(3) 0.0322(9) Uani 1 1 d . . .
H2 H 0.3957 0.5674 0.8872 0.039 Uiso 1 1 calc R . .
C3 C 0.4572(5) 0.4063(4) 0.8676(3) 0.0387(10) Uani 1 1 d . . .
H3 H 0.3946 0.3836 0.9110 0.046 Uiso 1 1 calc R . .
C4 C 0.5487(6) 0.3286(4) 0.8189(3) 0.0441(11) Uani 1 1 d . . .
H4 H 0.5468 0.2543 0.8293 0.053 Uiso 1 1 calc R . .
C5 C 0.6413(5) 0.3616(3) 0.7559(3) 0.0391(10) Uani 1 1 d . . .
H5 H 0.7041 0.3097 0.7242 0.047 Uiso 1 1 calc R . .
C6 C 0.6443(4) 0.4741(3) 0.7374(3) 0.0282(8) Uani 1 1 d . . .
C7 C 0.7451(4) 0.5026(3) 0.6721(3) 0.0277(8) Uani 1 1 d . . .
H7 H 0.8019 0.4451 0.6422 0.033 Uiso 1 1 calc R . .
C8 C 0.8724(5) 0.6281(3) 0.5011(3) 0.0271(9) Uani 1 1 d . . .
C9 C 0.7065(5) 0.6124(3) 0.4365(3) 0.0317(9) Uani 1 1 d . . .
H9A H 0.7199 0.6390 0.3793 0.048 Uiso 1 1 calc R . .
H9B H 0.6355 0.6573 0.4723 0.048 Uiso 1 1 calc R . .
H9C H 0.6577 0.5309 0.4166 0.048 Uiso 1 1 calc R . .
C10 C 1.0570(5) 0.6335(3) 0.6294(3) 0.0279(8) Uani 1 1 d . . .
C11 C 1.1290(5) 0.6253(4) 0.7296(3) 0.0355(9) Uani 1 1 d . . .
H11A H 1.2475 0.6476 0.7414 0.053 Uiso 1 1 calc R . .
H11B H 1.1020 0.5460 0.7335 0.053 Uiso 1 1 calc R . .
H11C H 1.0839 0.6769 0.7783 0.053 Uiso 1 1 calc R . .
C12 C 0.8870(5) 0.9499(3) 0.6857(3) 0.0299(8) Uani 1 1 d . . .
C13 C 0.9984(5) 0.9943(4) 0.6320(3) 0.0381(9) Uani 1 1 d . . .
H13 H 1.0292 0.9425 0.5800 0.046 Uiso 1 1 calc R . .
C14 C 1.0617(6) 1.1103(4) 0.6541(3) 0.0414(10) Uani 1 1 d . . .
H14 H 1.1333 1.1361 0.6163 0.050 Uiso 1 1 calc R . .
C15 C 1.0214(6) 1.1919(4) 0.7325(3) 0.0433(11) Uani 1 1 d . . .
H15 H 1.0660 1.2712 0.7473 0.052 Uiso 1 1 calc R . .
C16 C 0.9147(5) 1.1524(3) 0.7872(3) 0.0349(9) Uani 1 1 d . . .
H16 H 0.8882 1.2055 0.8400 0.042 Uiso 1 1 calc R . .
C17 C 0.8444(4) 1.0325(3) 0.7646(3) 0.0285(8) Uani 1 1 d . . .
C18 C 0.7360(4) 1.0001(3) 0.8263(2) 0.0270(8) Uani 1 1 d . . .
H18 H 0.7194 1.0588 0.8788 0.032 Uiso 1 1 calc R . .
C19 C 0.6112(6) 0.8428(4) 0.9665(3) 0.0408(11) Uani 1 1 d . . .
C20 C 0.7840(7) 0.8226(4) 0.9955(3) 0.0548(13) Uani 1 1 d . . .
H20A H 0.7914 0.7936 1.0530 0.082 Uiso 1 1 calc R . .
H20B H 0.8595 0.8952 1.0098 0.082 Uiso 1 1 calc R . .
H20C H 0.8124 0.7660 0.9425 0.082 Uiso 1 1 calc R . .
C21 C 0.3971(6) 0.8870(4) 0.8807(3) 0.0456(11) Uani 1 1 d . . .
C22 C 0.2953(6) 0.9262(5) 0.8058(4) 0.0665(17) Uani 1 1 d . . .
H22A H 0.1828 0.9204 0.8165 0.100 Uiso 1 1 calc R . .
H22B H 0.2982 0.8777 0.7416 0.100 Uiso 1 1 calc R . .
H22C H 0.3379 1.0064 0.8100 0.100 Uiso 1 1 calc R . .
O3 O 0.4659(3) 0.7566(2) 0.59340(19) 0.0313(6) Uani 1 1 d . . .
H3A H 0.3700 0.7231 0.5853 0.047 Uiso 1 1 d R . .
C23 C 0.4547(8) 0.8626(5) 0.5673(5) 0.0768(19) Uani 1 1 d . . .
H23A H 0.4114 0.9135 0.6185 0.092 Uiso 1 1 calc R . .
H23B H 0.5669 0.8998 0.5691 0.092 Uiso 1 1 calc R . .
C24 C 0.3608(9) 0.8602(6) 0.4779(6) 0.101(3) Uani 1 1 d . . .
H24A H 0.3998 0.8095 0.4256 0.152 Uiso 1 1 calc R . .
H24B H 0.3709 0.9382 0.4694 0.152 Uiso 1 1 calc R . .
H24C H 0.2465 0.8313 0.4766 0.152 Uiso 1 1 calc R . .
O4A O 0.0734(8) 0.6796(5) 0.9784(5) 0.034(2) Uani 0.422(10) 1 d PU . .
O4B O 0.0874(12) 0.5634(12) 0.9788(6) 0.022(4) Uani 0.253(16) 1 d PU . .
O4C O 0.0476(14) 0.4914(15) 0.9836(7) 0.052(4) Uani 0.325(16) 1 d PU . .

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 0.0277(5) 0.0179(4) 0.0270(4) 0.0040(2) 0.0086(3) 0.0007(2)
N1 0.0278(16) 0.0224(15) 0.0245(14) 0.0028(11) 0.0038(12) 0.0004(11)
N2 0.0261(17) 0.0219(14) 0.0228(14) 0.0035(11) 0.0100(13) 0.0024(11)
N3 0.0287(19) 0.0259(15) 0.0284(16) 0.0055(12) 0.0069(14) 0.0010(12)
N4 0.0276(17) 0.0260(15) 0.0298(16) 0.0050(12) 0.0067(14) 0.0011(12)
N5 0.0318(17) 0.0232(15) 0.0261(15) 0.0047(12) 0.0076(13) 0.0062(12)
N6 0.0330(18) 0.0242(15) 0.0258(15) -0.0008(12) 0.0092(14) 0.0020(12)
N7 0.074(3) 0.057(3) 0.032(2) -0.0071(17) 0.025(2) -0.031(2)
N8 0.052(3) 0.082(3) 0.041(2) -0.027(2) 0.023(2) -0.032(2)
O1 0.0307(14) 0.0225(13) 0.0323(13) 0.0078(10) 0.0085(11) 0.0036(10)
O2 0.0379(16) 0.0221(14) 0.0319(14) 0.0017(11) 0.0132(12) -0.0031(11)
C1 0.0256(18) 0.0266(18) 0.0272(17) 0.0077(14) -0.0001(15) 0.0015(13)
C2 0.031(2) 0.035(2) 0.0291(18) 0.0114(15) 0.0042(16) -0.0006(15)
C3 0.039(2) 0.039(2) 0.041(2) 0.0217(17) 0.0060(18) -0.0014(17)
C4 0.049(3) 0.034(2) 0.057(3) 0.026(2) 0.010(2) 0.0074(18)
C5 0.043(2) 0.0264(19) 0.053(2) 0.0177(17) 0.0103(19) 0.0089(16)
C6 0.0251(18) 0.0246(18) 0.0340(18) 0.0114(14) 0.0030(15) -0.0035(13)
C7 0.0308(19) 0.0205(17) 0.0283(17) 0.0026(14) 0.0008(15) 0.0042(13)
C8 0.033(2) 0.0198(16) 0.0257(18) 0.0016(13) 0.0053(16) 0.0023(14)
C9 0.031(2) 0.038(2) 0.0240(17) 0.0054(15) 0.0061(15) 0.0022(15)
C10 0.0256(19) 0.0252(18) 0.0298(19) 0.0024(15) 0.0071(16) 0.0005(14)
C11 0.027(2) 0.046(2) 0.034(2) 0.0113(17) 0.0051(16) 0.0059(16)
C12 0.035(2) 0.0262(18) 0.0263(18) 0.0085(14) 0.0017(15) -0.0016(14)
C13 0.043(2) 0.034(2) 0.0325(19) 0.0081(16) 0.0072(17) -0.0073(17)
C14 0.048(2) 0.040(2) 0.035(2) 0.0167(17) 0.0050(18) -0.0085(17)
C15 0.054(3) 0.0270(19) 0.041(2) 0.0098(17) -0.004(2) -0.0108(17)
C16 0.044(2) 0.0235(18) 0.0323(19) 0.0062(15) 0.0015(17) -0.0023(16)
C17 0.0295(19) 0.0232(17) 0.0303(18) 0.0087(14) 0.0005(15) -0.0022(14)
C18 0.0334(19) 0.0199(17) 0.0247(16) 0.0025(13) -0.0009(15) 0.0072(14)
C19 0.059(3) 0.034(2) 0.028(2) 0.0076(16) 0.010(2) -0.0019(19)
C20 0.074(3) 0.052(3) 0.039(2) 0.018(2) 0.000(2) 0.015(2)
C21 0.038(2) 0.046(2) 0.039(2) -0.0161(18) 0.017(2) -0.0006(18)
C22 0.038(3) 0.077(4) 0.058(3) -0.028(3) -0.006(2) 0.021(2)
O3 0.0290(14) 0.0292(14) 0.0364(14) 0.0143(11) 0.0039(11) -0.0008(10)
C23 0.087(4) 0.048(3) 0.088(4) 0.044(3) -0.027(3) -0.015(3)
C24 0.084(4) 0.076(4) 0.137(6) 0.083(4) -0.048(4) -0.036(3)
O4A 0.037(4) 0.021(3) 0.041(4) 0.003(2) 0.009(3) 0.002(2)
O4B 0.015(5) 0.026(7) 0.020(5) 0.003(4) 0.004(3) -0.007(4)
O4C 0.047(7) 0.047(8) 0.057(6) 0.003(5) 0.023(4) 0.002(5)

_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 O1 1.904(3) . ?
Cu1 O2 1.905(3) . ?
Cu1 N5 2.004(3) . ?
Cu1 N1 2.009(3) . ?
Cu1 O3 2.299(3) . ?
N1 C7 1.301(5) . ?
N1 N2 1.407(5) . ?
N2 C10 1.365(5) . ?
N2 C8 1.367(5) . ?
N3 C8 1.293(5) . ?
N3 N4 1.415(4) . ?
N4 C10 1.290(5) . ?
N5 C18 1.309(5) . ?
N5 N6 1.404(5) . ?
N6 C19 1.363(5) . ?
N6 C21 1.374(6) . ?
N7 C19 1.293(7) . ?
N7 N8 1.372(8) . ?
N8 C21 1.310(7) . ?
O1 C1 1.307(4) . ?
O2 C12 1.303(4) . ?
C1 C2 1.411(5) . ?
C1 C6 1.423(5) . ?
C2 C3 1.380(6) . ?
C2 H2 0.9300 . ?
C3 C4 1.385(7) . ?
C3 H3 0.9300 . ?
C4 C5 1.359(7) . ?
C4 H4 0.9300 . ?
C5 C6 1.425(5) . ?
C5 H5 0.9300 . ?
C6 C7 1.410(5) . ?
C7 H7 0.9300 . ?
C8 C9 1.495(5) . ?
C9 H9A 0.9600 . ?
C9 H9B 0.9600 . ?
C9 H9C 0.9600 . ?
C10 C11 1.493(5) . ?
C11 H11A 0.9600 . ?
C11 H11B 0.9600 . ?
C11 H11C 0.9600 . ?
C12 C13 1.413(6) . ?
C12 C17 1.420(5) . ?
C13 C14 1.357(6) . ?
C13 H13 0.9300 . ?
C14 C15 1.401(7) . ?
C14 H14 0.9300 . ?
C15 C16 1.373(6) . ?
C15 H15 0.9300 . ?
C16 C17 1.412(5) . ?
C16 H16 0.9300 . ?
C17 C18 1.426(6) . ?
C18 H18 0.9300 . ?
C19 C20 1.490(7) . ?
C20 H20A 0.9600 . ?
C20 H20B 0.9600 . ?
C20 H20C 0.9600 . ?
C21 C22 1.462(8) . ?
C22 H22A 0.9600 . ?
C22 H22B 0.9600 . ?
C22 H22C 0.9600 . ?
O3 C23 1.410(5) . ?
O3 H3A 0.8200 . ?
C23 C24 1.382(8) . ?
C23 H23A 0.9700 . ?
C23 H23B 0.9700 . ?
C24 H24A 0.9600 . ?
C24 H24B 0.9600 . ?
C24 H24C 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
O1 Cu1 O2 175.64(10) . . ?
O1 Cu1 N5 89.25(12) . . ?
O2 Cu1 N5 90.57(12) . . ?
O1 Cu1 N1 89.74(12) . . ?
O2 Cu1 N1 88.95(12) . . ?
N5 Cu1 N1 160.12(13) . . ?
O1 Cu1 O3 93.97(10) . . ?
O2 Cu1 O3 90.37(11) . . ?
N5 Cu1 O3 97.05(11) . . ?
N1 Cu1 O3 102.82(11) . . ?
C7 N1 N2 113.2(3) . . ?
C7 N1 Cu1 126.1(3) . . ?
N2 N1 Cu1 118.9(2) . . ?
C10 N2 C8 106.0(3) . . ?
C10 N2 N1 125.3(3) . . ?
C8 N2 N1 127.4(3) . . ?
C8 N3 N4 106.5(3) . . ?
C10 N4 N3 108.1(3) . . ?
C18 N5 N6 113.7(3) . . ?
C18 N5 Cu1 127.0(3) . . ?
N6 N5 Cu1 119.0(2) . . ?
C19 N6 C21 106.3(4) . . ?
C19 N6 N5 125.7(3) . . ?
C21 N6 N5 126.6(3) . . ?
C19 N7 N8 108.1(4) . . ?
C21 N8 N7 108.5(4) . . ?
C1 O1 Cu1 129.7(2) . . ?
C12 O2 Cu1 130.1(3) . . ?
O1 C1 C2 118.5(3) . . ?
O1 C1 C6 123.6(3) . . ?
C2 C1 C6 117.8(3) . . ?
C3 C2 C1 120.9(4) . . ?
C3 C2 H2 119.6 . . ?
C1 C2 H2 119.6 . . ?
C2 C3 C4 121.3(4) . . ?
C2 C3 H3 119.3 . . ?
C4 C3 H3 119.3 . . ?
C5 C4 C3 119.5(4) . . ?
C5 C4 H4 120.2 . . ?
C3 C4 H4 120.2 . . ?
C4 C5 C6 121.4(4) . . ?
C4 C5 H5 119.3 . . ?
C6 C5 H5 119.3 . . ?
C7 C6 C1 122.9(3) . . ?
C7 C6 C5 118.1(3) . . ?
C1 C6 C5 119.0(3) . . ?
N1 C7 C6 125.5(3) . . ?
N1 C7 H7 117.3 . . ?
C6 C7 H7 117.3 . . ?
N3 C8 N2 110.1(3) . . ?
N3 C8 C9 127.2(3) . . ?
N2 C8 C9 122.6(4) . . ?
C8 C9 H9A 109.5 . . ?
C8 C9 H9B 109.5 . . ?
H9A C9 H9B 109.5 . . ?
C8 C9 H9C 109.5 . . ?
H9A C9 H9C 109.5 . . ?
H9B C9 H9C 109.5 . . ?
N4 C10 N2 109.3(3) . . ?
N4 C10 C11 127.8(3) . . ?
N2 C10 C11 122.9(3) . . ?
C10 C11 H11A 109.5 . . ?
C10 C11 H11B 109.5 . . ?
H11A C11 H11B 109.5 . . ?
C10 C11 H11C 109.5 . . ?
H11A C11 H11C 109.5 . . ?
H11B C11 H11C 109.5 . . ?
O2 C12 C13 118.5(3) . . ?
O2 C12 C17 124.7(3) . . ?
C13 C12 C17 116.8(3) . . ?
C14 C13 C12 122.0(4) . . ?
C14 C13 H13 119.0 . . ?
C12 C13 H13 119.0 . . ?
C13 C14 C15 121.4(4) . . ?
C13 C14 H14 119.3 . . ?
C15 C14 H14 119.3 . . ?
C16 C15 C14 118.5(4) . . ?
C16 C15 H15 120.7 . . ?
C14 C15 H15 120.7 . . ?
C15 C16 C17 121.3(4) . . ?
C15 C16 H16 119.4 . . ?
C17 C16 H16 119.4 . . ?
C16 C17 C12 120.0(4) . . ?
C16 C17 C18 117.0(3) . . ?
C12 C17 C18 123.0(3) . . ?
N5 C18 C17 124.5(3) . . ?
N5 C18 H18 117.7 . . ?
C17 C18 H18 117.7 . . ?
N7 C19 N6 109.2(4) . . ?
N7 C19 C20 128.3(4) . . ?
N6 C19 C20 122.5(4) . . ?
C19 C20 H20A 109.5 . . ?
C19 C20 H20B 109.5 . . ?
H20A C20 H20B 109.5 . . ?
C19 C20 H20C 109.5 . . ?
H20A C20 H20C 109.5 . . ?
H20B C20 H20C 109.5 . . ?
N8 C21 N6 107.8(5) . . ?
N8 C21 C22 127.4(5) . . ?
N6 C21 C22 124.8(4) . . ?
C21 C22 H22A 109.5 . . ?
C21 C22 H22B 109.5 . . ?
H22A C22 H22B 109.5 . . ?
C21 C22 H22C 109.5 . . ?
H22A C22 H22C 109.5 . . ?
H22B C22 H22C 109.5 . . ?
C23 O3 Cu1 120.0(3) . . ?
C23 O3 H3A 105.8 . . ?
Cu1 O3 H3A 125.1 . . ?
C24 C23 O3 119.5(5) . . ?
C24 C23 H23A 107.4 . . ?
O3 C23 H23A 107.4 . . ?
C24 C23 H23B 107.4 . . ?
O3 C23 H23B 107.4 . . ?
H23A C23 H23B 107.0 . . ?
C23 C24 H24A 109.5 . . ?
C23 C24 H24B 109.5 . . ?
H24A C24 H24B 109.5 . . ?
C23 C24 H24C 109.5 . . ?
H24A C24 H24C 109.5 . . ?
H24B C24 H24C 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
O1 Cu1 N1 C7 -13.1(3) . . . . ?
O2 Cu1 N1 C7 162.8(3) . . . . ?
N5 Cu1 N1 C7 74.0(5) . . . . ?
O3 Cu1 N1 C7 -107.1(3) . . . . ?
O1 Cu1 N1 N2 -177.0(2) . . . . ?
O2 Cu1 N1 N2 -1.2(2) . . . . ?
N5 Cu1 N1 N2 -89.9(4) . . . . ?
O3 Cu1 N1 N2 89.0(2) . . . . ?
C7 N1 N2 C10 -76.3(4) . . . . ?
Cu1 N1 N2 C10 89.7(3) . . . . ?
C7 N1 N2 C8 118.8(3) . . . . ?
Cu1 N1 N2 C8 -75.3(4) . . . . ?
C8 N3 N4 C10 0.1(4) . . . . ?
O1 Cu1 N5 C18 174.3(3) . . . . ?
O2 Cu1 N5 C18 -1.4(3) . . . . ?
N1 Cu1 N5 C18 87.1(4) . . . . ?
O3 Cu1 N5 C18 -91.8(3) . . . . ?
O1 Cu1 N5 N6 0.9(2) . . . . ?
O2 Cu1 N5 N6 -174.7(2) . . . . ?
N1 Cu1 N5 N6 -86.2(4) . . . . ?
O3 Cu1 N5 N6 94.8(2) . . . . ?
C18 N5 N6 C19 -99.3(4) . . . . ?
Cu1 N5 N6 C19 74.9(4) . . . . ?
C18 N5 N6 C21 95.5(4) . . . . ?
Cu1 N5 N6 C21 -90.3(4) . . . . ?
C19 N7 N8 C21 -0.8(5) . . . . ?
N5 Cu1 O1 C1 -142.7(3) . . . . ?
N1 Cu1 O1 C1 17.4(3) . . . . ?
O3 Cu1 O1 C1 120.3(3) . . . . ?
N5 Cu1 O2 C12 -1.8(3) . . . . ?
N1 Cu1 O2 C12 -161.9(3) . . . . ?
O3 Cu1 O2 C12 95.3(3) . . . . ?
Cu1 O1 C1 C2 165.1(2) . . . . ?
Cu1 O1 C1 C6 -15.4(5) . . . . ?
O1 C1 C2 C3 178.1(3) . . . . ?
C6 C1 C2 C3 -1.5(5) . . . . ?
C1 C2 C3 C4 0.9(6) . . . . ?
C2 C3 C4 C5 0.5(6) . . . . ?
C3 C4 C5 C6 -1.1(7) . . . . ?
O1 C1 C6 C7 2.7(5) . . . . ?
C2 C1 C6 C7 -177.8(3) . . . . ?
O1 C1 C6 C5 -178.7(3) . . . . ?
C2 C1 C6 C5 0.9(5) . . . . ?
C4 C5 C6 C7 179.2(4) . . . . ?
C4 C5 C6 C1 0.4(6) . . . . ?
N2 N1 C7 C6 171.8(3) . . . . ?
Cu1 N1 C7 C6 7.0(5) . . . . ?
C1 C6 C7 N1 1.1(5) . . . . ?
C5 C6 C7 N1 -177.6(3) . . . . ?
N4 N3 C8 N2 -1.6(4) . . . . ?
N4 N3 C8 C9 -178.6(3) . . . . ?
C10 N2 C8 N3 2.6(4) . . . . ?
N1 N2 C8 N3 169.8(3) . . . . ?
C10 N2 C8 C9 179.7(3) . . . . ?
N1 N2 C8 C9 -13.0(5) . . . . ?
N3 N4 C10 N2 1.6(4) . . . . ?
N3 N4 C10 C11 178.7(4) . . . . ?
C8 N2 C10 N4 -2.5(4) . . . . ?
N1 N2 C10 N4 -170.1(3) . . . . ?
C8 N2 C10 C11 -179.8(3) . . . . ?
N1 N2 C10 C11 12.6(5) . . . . ?
Cu1 O2 C12 C13 -178.4(3) . . . . ?
Cu1 O2 C12 C17 2.4(5) . . . . ?
O2 C12 C13 C14 -179.5(4) . . . . ?
C17 C12 C13 C14 -0.2(6) . . . . ?
C12 C13 C14 C15 1.0(6) . . . . ?
C13 C14 C15 C16 -0.4(6) . . . . ?
C14 C15 C16 C17 -0.9(6) . . . . ?
C15 C16 C17 C12 1.6(6) . . . . ?
C15 C16 C17 C18 179.5(3) . . . . ?
O2 C12 C17 C16 178.2(3) . . . . ?
C13 C12 C17 C16 -1.0(5) . . . . ?
O2 C12 C17 C18 0.4(6) . . . . ?
C13 C12 C17 C18 -178.8(3) . . . . ?
N6 N5 C18 C17 177.6(3) . . . . ?
Cu1 N5 C18 C17 4.0(5) . . . . ?
C16 C17 C18 N5 178.5(3) . . . . ?
C12 C17 C18 N5 -3.7(5) . . . . ?
N8 N7 C19 N6 1.9(5) . . . . ?
N8 N7 C19 C20 -178.4(4) . . . . ?
C21 N6 C19 N7 -2.3(5) . . . . ?
N5 N6 C19 N7 -169.9(4) . . . . ?
C21 N6 C19 C20 178.0(4) . . . . ?
N5 N6 C19 C20 10.4(6) . . . . ?
N7 N8 C21 N6 -0.6(5) . . . . ?
N7 N8 C21 C22 -178.3(4) . . . . ?
C19 N6 C21 N8 1.8(5) . . . . ?
N5 N6 C21 N8 169.3(4) . . . . ?
C19 N6 C21 C22 179.5(4) . . . . ?
N5 N6 C21 C22 -13.0(6) . . . . ?
O1 Cu1 O3 C23 138.0(4) . . . . ?
O2 Cu1 O3 C23 -42.4(4) . . . . ?
N5 Cu1 O3 C23 48.3(5) . . . . ?
N1 Cu1 O3 C23 -131.4(4) . . . . ?
Cu1 O3 C23 C24 160.5(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
_geom_hbond_publ_flag
O3 H3A N4 0.82 1.95 2.769(4) 174.9 1_455 y

_diffrn_measured_fraction_theta_max 0.903
_diffrn_reflns_theta_full        27.40
_diffrn_measured_fraction_theta_full 0.903
_refine_diff_density_max         1.061
_refine_diff_density_min         -1.351
_refine_diff_density_rms         0.153

data_II
_database_code_depnum_ccdc_archive 'CCDC 809857'
#TrackingRef '- CCDC809856-7.cif'

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C22 H24 Cl2 Cu N8 O4, 2(C2 H6 O), 2(C H4 O)'
_chemical_formula_sum            'C28 H44 Cl2 Cu N8 O8'
_chemical_formula_weight         755.15

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'
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'
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'

_symmetry_cell_setting           triclinic
_symmetry_space_group_name_H-M   'P -1'
_symmetry_space_group_name_Hall  '-P 1'

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

_cell_length_a                   7.7403(6)
_cell_length_b                   8.7315(7)
_cell_length_c                   15.534(2)
_cell_angle_alpha                102.878(2)
_cell_angle_beta                 100.102(2)
_cell_angle_gamma                101.399(1)
_cell_volume                     976.44(15)
_cell_formula_units_Z            1
_cell_measurement_temperature    298(2)
_cell_measurement_reflns_used    2313
_cell_measurement_theta_min      2.47
_cell_measurement_theta_max      22.29

_exptl_crystal_description       block
_exptl_crystal_colour            blue
_exptl_crystal_size_max          0.40
_exptl_crystal_size_mid          0.30
_exptl_crystal_size_min          0.20
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.284
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             395
_exptl_absorpt_coefficient_mu    0.748
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.7541
_exptl_absorpt_correction_T_max  0.8648
_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  ?
_diffrn_measurement_method       ?
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            10558
_diffrn_reflns_av_R_equivalents  0.0345
_diffrn_reflns_av_sigmaI/netI    0.0403
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_theta_min         2.47
_diffrn_reflns_theta_max         25.18
_reflns_number_total             3501
_reflns_number_gt                2452
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_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^)+(0.1000P)^2^+0.6030P] 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_number_reflns         3501
_refine_ls_number_parameters     218
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0883
_refine_ls_R_factor_gt           0.0599
_refine_ls_wR_factor_ref         0.1795
_refine_ls_wR_factor_gt          0.1616
_refine_ls_goodness_of_fit_ref   1.004
_refine_ls_restrained_S_all      1.004
_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 0.5000 0.5000 0.5000 0.0583(3) Uani 1 2 d S . .
N1 N 0.6887(4) 0.6292(3) 0.4518(2) 0.0456(7) Uani 1 1 d . . .
N2 N 0.7754(4) 0.7920(3) 0.4986(2) 0.0475(8) Uani 1 1 d . . .
N3 N 0.9244(5) 1.0000(4) 0.6095(2) 0.0597(9) Uani 1 1 d . . .
N4 N 0.8177(5) 1.0528(4) 0.5452(3) 0.0606(9) Uani 1 1 d . . .
C1 C 0.6485(5) 0.4301(5) 0.3097(3) 0.0503(9) Uani 1 1 d . . .
C2 C 0.5133(5) 0.3082(4) 0.3238(3) 0.0495(9) Uani 1 1 d . . .
C3 C 0.4431(6) 0.1633(5) 0.2541(3) 0.0619(11) Uani 1 1 d . . .
H3 H 0.3565 0.0807 0.2624 0.074 Uiso 1 1 calc R . .
C4 C 0.4988(7) 0.1412(6) 0.1751(3) 0.0746(13) Uani 1 1 d . . .
H4 H 0.4489 0.0453 0.1294 0.090 Uiso 1 1 calc R . .
C5 C 0.6309(8) 0.2624(7) 0.1625(3) 0.0824(15) Uani 1 1 d . . .
C6 C 0.7053(7) 0.4035(6) 0.2272(3) 0.0703(12) Uani 1 1 d . . .
H6 H 0.7936 0.4828 0.2175 0.084 Uiso 1 1 calc R . .
C7 C 0.7283(5) 0.5836(4) 0.3745(3) 0.0501(9) Uani 1 1 d . . .
H7 H 0.8159 0.6563 0.3597 0.060 Uiso 1 1 calc R . .
C8 C 0.8957(5) 0.8437(5) 0.5801(3) 0.0526(10) Uani 1 1 d . . .
C9 C 0.9864(7) 0.7400(6) 0.6246(4) 0.0823(15) Uani 1 1 d . . .
H9A H 1.0841 0.8066 0.6740 0.124 Uiso 1 1 calc R . .
H9B H 1.0333 0.6724 0.5816 0.124 Uiso 1 1 calc R . .
H9C H 0.9012 0.6733 0.6474 0.124 Uiso 1 1 calc R . .
C10 C 0.7282(5) 0.9256(5) 0.4794(3) 0.0520(10) Uani 1 1 d . . .
C11 C 0.6048(6) 0.9260(6) 0.3966(3) 0.0704(12) Uani 1 1 d . . .
H11A H 0.6626 0.9085 0.3467 0.106 Uiso 1 1 calc R . .
H11B H 0.5740 1.0288 0.4044 0.106 Uiso 1 1 calc R . .
H11C H 0.4967 0.8412 0.3844 0.106 Uiso 1 1 calc R . .
C12 C 0.8707(18) 0.8543(15) 0.1435(10) 0.273(9) Uani 1 1 d . . .
H12A H 0.9679 0.9133 0.1239 0.410 Uiso 1 1 calc R . .
H12B H 0.7970 0.9251 0.1638 0.410 Uiso 1 1 calc R . .
H12C H 0.7982 0.7654 0.0939 0.410 Uiso 1 1 calc R . .
C13 C 0.2196(19) 0.4874(19) 0.1637(11) 0.207(5) Uani 1 1 d . . .
H13A H 0.2746 0.4049 0.1811 0.248 Uiso 1 1 calc R . .
H13B H 0.1113 0.4363 0.1158 0.248 Uiso 1 1 calc R . .
C14 C 0.342(3) 0.602(3) 0.1388(13) 0.307(10) Uani 1 1 d . . .
H14A H 0.4224 0.5496 0.1096 0.460 Uiso 1 1 calc R . .
H14B H 0.4111 0.6853 0.1921 0.460 Uiso 1 1 calc R . .
H14C H 0.2764 0.6494 0.0979 0.460 Uiso 1 1 calc R . .
Cl1 Cl 0.6977(3) 0.2326(2) 0.05899(12) 0.1475(9) Uani 1 1 d . . .
O1 O 0.4540(4) 0.3225(3) 0.39735(19) 0.0616(8) Uani 1 1 d . . .
O2 O 0.2537(5) 0.6278(4) 0.4214(3) 0.0971(12) Uani 1 1 d . . .
H2A H 0.2315 0.6029 0.3658 0.146 Uiso 1 1 d R . .
H2B H 0.2372 0.7184 0.4385 0.146 Uiso 1 1 d R . .
O3 O 0.9505(8) 0.7879(5) 0.2234(3) 0.1347(18) Uani 1 1 d . . .
H3A H 1.0151 0.8659 0.2638 0.202 Uiso 1 1 d R . .
O4 O 0.1834(11) 0.5923(10) 0.2395(4) 0.192(3) Uani 1 1 d . . .
H4A H 0.1650 0.6832 0.2484 0.288 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 0.0716(5) 0.0422(4) 0.0517(5) 0.0066(3) 0.0259(4) -0.0108(3)
N1 0.0492(17) 0.0363(15) 0.0485(18) 0.0119(13) 0.0134(14) 0.0017(13)
N2 0.0480(17) 0.0356(16) 0.058(2) 0.0152(14) 0.0164(15) 0.0011(13)
N3 0.064(2) 0.0437(18) 0.063(2) 0.0087(16) 0.0161(18) -0.0005(16)
N4 0.070(2) 0.0413(18) 0.070(2) 0.0124(17) 0.0253(19) 0.0073(16)
C1 0.056(2) 0.050(2) 0.048(2) 0.0161(17) 0.0163(18) 0.0135(17)
C2 0.055(2) 0.045(2) 0.048(2) 0.0137(17) 0.0121(18) 0.0099(17)
C3 0.071(3) 0.051(2) 0.054(2) 0.0085(19) 0.011(2) 0.0030(19)
C4 0.093(3) 0.059(3) 0.059(3) 0.000(2) 0.015(2) 0.011(2)
C5 0.105(4) 0.082(3) 0.059(3) 0.009(3) 0.036(3) 0.018(3)
C6 0.086(3) 0.066(3) 0.060(3) 0.016(2) 0.033(2) 0.009(2)
C7 0.049(2) 0.045(2) 0.060(3) 0.0220(18) 0.0182(18) 0.0069(16)
C8 0.047(2) 0.047(2) 0.059(3) 0.0170(18) 0.0108(19) -0.0001(17)
C9 0.078(3) 0.062(3) 0.094(4) 0.028(3) -0.008(3) 0.003(2)
C10 0.054(2) 0.045(2) 0.063(3) 0.0201(19) 0.025(2) 0.0097(17)
C11 0.075(3) 0.061(3) 0.081(3) 0.031(2) 0.015(3) 0.018(2)
C12 0.249(14) 0.197(12) 0.293(17) -0.032(12) -0.099(13) 0.125(10)
C13 0.183(12) 0.215(14) 0.216(14) 0.039(12) 0.016(10) 0.083(11)
C14 0.28(2) 0.41(3) 0.33(2) 0.22(2) 0.120(17) 0.12(2)
Cl1 0.211(2) 0.1296(15) 0.0800(11) -0.0084(10) 0.0833(13) -0.0117(14)
O1 0.0756(18) 0.0447(15) 0.0553(17) 0.0061(12) 0.0265(15) -0.0078(13)
O2 0.119(3) 0.0498(19) 0.115(3) 0.0209(19) 0.013(2) 0.0169(19)
O3 0.190(5) 0.094(3) 0.093(3) 0.004(3) -0.008(3) 0.033(3)
O4 0.250(8) 0.232(8) 0.111(4) 0.021(5) 0.040(5) 0.128(7)

_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 O1 1.885(3) . ?
Cu1 O1 1.885(3) 2_666 ?
Cu1 N1 2.019(3) . ?
Cu1 N1 2.019(3) 2_666 ?
N1 C7 1.288(5) . ?
N1 N2 1.411(4) . ?
N2 C8 1.356(5) . ?
N2 C10 1.367(5) . ?
N3 C8 1.300(5) . ?
N3 N4 1.399(5) . ?
N4 C10 1.304(5) . ?
C1 C6 1.411(6) . ?
C1 C2 1.422(5) . ?
C1 C7 1.430(5) . ?
C2 O1 1.294(5) . ?
C2 C3 1.408(5) . ?
C3 C4 1.358(6) . ?
C3 H3 0.9300 . ?
C4 C5 1.392(7) . ?
C4 H4 0.9300 . ?
C5 C6 1.351(7) . ?
C5 Cl1 1.754(5) . ?
C6 H6 0.9300 . ?
C7 H7 0.9300 . ?
C8 C9 1.466(6) . ?
C9 H9A 0.9600 . ?
C9 H9B 0.9600 . ?
C9 H9C 0.9600 . ?
C10 C11 1.463(6) . ?
C11 H11A 0.9600 . ?
C11 H11B 0.9600 . ?
C11 H11C 0.9600 . ?
C12 O3 1.566(13) . ?
C12 H12A 0.9600 . ?
C12 H12B 0.9600 . ?
C12 H12C 0.9600 . ?
C13 C14 1.406(18) . ?
C13 O4 1.428(14) . ?
C13 H13A 0.9700 . ?
C13 H13B 0.9700 . ?
C14 H14A 0.9600 . ?
C14 H14B 0.9600 . ?
C14 H14C 0.9600 . ?
O2 H2A 0.8200 . ?
O2 H2B 0.8200 . ?
O3 H3A 0.8205 . ?
O4 H4A 0.8200 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
O1 Cu1 O1 179.999(1) . 2_666 ?
O1 Cu1 N1 90.67(11) . . ?
O1 Cu1 N1 89.33(11) 2_666 . ?
O1 Cu1 N1 89.33(11) . 2_666 ?
O1 Cu1 N1 90.67(11) 2_666 2_666 ?
N1 Cu1 N1 180.000(1) . 2_666 ?
C7 N1 N2 113.3(3) . . ?
C7 N1 Cu1 126.0(2) . . ?
N2 N1 Cu1 120.3(2) . . ?
C8 N2 C10 107.0(3) . . ?
C8 N2 N1 126.0(3) . . ?
C10 N2 N1 125.9(3) . . ?
C8 N3 N4 107.7(3) . . ?
C10 N4 N3 107.6(3) . . ?
C6 C1 C2 119.7(4) . . ?
C6 C1 C7 117.2(4) . . ?
C2 C1 C7 123.1(3) . . ?
O1 C2 C3 118.6(3) . . ?
O1 C2 C1 123.7(3) . . ?
C3 C2 C1 117.7(4) . . ?
C4 C3 C2 121.5(4) . . ?
C4 C3 H3 119.3 . . ?
C2 C3 H3 119.3 . . ?
C3 C4 C5 119.9(4) . . ?
C3 C4 H4 120.0 . . ?
C5 C4 H4 120.0 . . ?
C6 C5 C4 121.4(4) . . ?
C6 C5 Cl1 119.5(4) . . ?
C4 C5 Cl1 119.0(4) . . ?
C5 C6 C1 119.8(4) . . ?
C5 C6 H6 120.1 . . ?
C1 C6 H6 120.1 . . ?
N1 C7 C1 125.2(3) . . ?
N1 C7 H7 117.4 . . ?
C1 C7 H7 117.4 . . ?
N3 C8 N2 109.0(4) . . ?
N3 C8 C9 125.8(4) . . ?
N2 C8 C9 125.0(4) . . ?
C8 C9 H9A 109.5 . . ?
C8 C9 H9B 109.5 . . ?
H9A C9 H9B 109.5 . . ?
C8 C9 H9C 109.5 . . ?
H9A C9 H9C 109.5 . . ?
H9B C9 H9C 109.5 . . ?
N4 C10 N2 108.6(4) . . ?
N4 C10 C11 125.9(4) . . ?
N2 C10 C11 125.5(4) . . ?
C10 C11 H11A 109.5 . . ?
C10 C11 H11B 109.5 . . ?
H11A C11 H11B 109.5 . . ?
C10 C11 H11C 109.5 . . ?
H11A C11 H11C 109.5 . . ?
H11B C11 H11C 109.5 . . ?
O3 C12 H12A 109.5 . . ?
O3 C12 H12B 109.5 . . ?
H12A C12 H12B 109.5 . . ?
O3 C12 H12C 109.5 . . ?
H12A C12 H12C 109.5 . . ?
H12B C12 H12C 109.5 . . ?
C14 C13 O4 99.1(14) . . ?
C14 C13 H13A 111.9 . . ?
O4 C13 H13A 111.9 . . ?
C14 C13 H13B 111.9 . . ?
O4 C13 H13B 111.9 . . ?
H13A C13 H13B 109.6 . . ?
C13 C14 H14A 109.5 . . ?
C13 C14 H14B 109.5 . . ?
H14A C14 H14B 109.5 . . ?
C13 C14 H14C 109.5 . . ?
H14A C14 H14C 109.5 . . ?
H14B C14 H14C 109.5 . . ?
C2 O1 Cu1 131.0(2) . . ?
H2A O2 H2B 107.7 . . ?
C12 O3 H3A 107.3 . . ?
C13 O4 H4A 133.1 . . ?

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
O1 Cu1 N1 C7 4.0(3) . . . . ?
O1 Cu1 N1 C7 -176.0(3) 2_666 . . . ?
O1 Cu1 N1 N2 176.0(3) . . . . ?
O1 Cu1 N1 N2 -4.0(3) 2_666 . . . ?
C7 N1 N2 C8 -117.6(4) . . . . ?
Cu1 N1 N2 C8 69.5(4) . . . . ?
C7 N1 N2 C10 76.0(4) . . . . ?
Cu1 N1 N2 C10 -96.9(4) . . . . ?
C8 N3 N4 C10 0.1(4) . . . . ?
C6 C1 C2 O1 179.8(4) . . . . ?
C7 C1 C2 O1 -2.2(6) . . . . ?
C6 C1 C2 C3 0.9(6) . . . . ?
C7 C1 C2 C3 178.9(4) . . . . ?
O1 C2 C3 C4 179.5(4) . . . . ?
C1 C2 C3 C4 -1.5(6) . . . . ?
C2 C3 C4 C5 1.3(8) . . . . ?
C3 C4 C5 C6 -0.4(8) . . . . ?
C3 C4 C5 Cl1 -178.8(4) . . . . ?
C4 C5 C6 C1 -0.2(8) . . . . ?
Cl1 C5 C6 C1 178.2(4) . . . . ?
C2 C1 C6 C5 -0.1(7) . . . . ?
C7 C1 C6 C5 -178.2(4) . . . . ?
N2 N1 C7 C1 -174.4(3) . . . . ?
Cu1 N1 C7 C1 -1.9(6) . . . . ?
C6 C1 C7 N1 178.1(4) . . . . ?
C2 C1 C7 N1 0.0(6) . . . . ?
N4 N3 C8 N2 0.5(4) . . . . ?
N4 N3 C8 C9 177.1(4) . . . . ?
C10 N2 C8 N3 -0.9(4) . . . . ?
N1 N2 C8 N3 -169.5(3) . . . . ?
C10 N2 C8 C9 -177.5(4) . . . . ?
N1 N2 C8 C9 14.0(6) . . . . ?
N3 N4 C10 N2 -0.7(4) . . . . ?
N3 N4 C10 C11 -177.9(4) . . . . ?
C8 N2 C10 N4 1.0(4) . . . . ?
N1 N2 C10 N4 169.5(3) . . . . ?
C8 N2 C10 C11 178.2(4) . . . . ?
N1 N2 C10 C11 -13.3(6) . . . . ?
C3 C2 O1 Cu1 -174.6(3) . . . . ?
C1 C2 O1 Cu1 6.5(6) . . . . ?
N1 Cu1 O1 C2 -6.4(4) . . . . ?
N1 Cu1 O1 C2 173.6(4) 2_666 . . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
_geom_hbond_publ_flag
O4 H4A O3 0.82 2.07 2.734(9) 138.3 1_455 y
O3 H3A N3 0.82 1.97 2.715(6) 150.0 2_776 y
O2 H2A O4 0.82 1.91 2.717(7) 168.0 . y
O2 H2B N4 0.82 2.09 2.902(5) 168.6 2_676 y

_diffrn_measured_fraction_theta_max 0.992
_diffrn_reflns_theta_full        25.18
_diffrn_measured_fraction_theta_full 0.992
_refine_diff_density_max         0.732
_refine_diff_density_min         -0.412
_refine_diff_density_rms         0.069