# Supplementary Material (ESI) for Chemical Communications
# This journal is (c) The Royal Society of Chemistry 2010

data_global
_journal_name_full               Chem.Commun.

# Attachment 'CCDC740931_Revision.cif'

# SUBMISSION DETAILS
_journal_coden_Cambridge         0182

_publ_contact_author_name        'Prof Dr Miaoli Zhu'
_publ_contact_author_address     
;
Institute of Molecular Science,
Shanxi University,
Taiyuan, Shanxi 030006,
People's Republic of China
;
_publ_contact_author_phone       '0086 351 701 7974'
_publ_contact_author_fax         ?
_publ_contact_author_email       miaoli@sxu.edu.cn

#==========================================================================
# TITLE AND AUTHOR LIST

_publ_section_title              
;
Potent inhibition of protein tyrosine phosphatase 1B by copper complexes:
implication to copper toxicity in biological systems
;
_publ_section_title_footnote     
;
?
;

# The loop structure below should contain the names and addresses of all
# authors, in the required order of publication. Repeat as necessary.

loop_
_publ_author_name
_publ_author_address

'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
;
'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
;
'Caixia Yuan.'
;
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
;
'Kai Pei.'
;
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
;
'Zhiwei Liu.'
;
Department of Chemistry and Biochemistry,
University of Massachusetts Dartmouth,
MA 02747, USA
;
;
Maolin Guo
;
;
Department of Chemistry and Biochemistry,
University of Massachusetts Dartmouth,
MA 02747, USA
;
'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
;
#==========================================================================
data_wqm_zp1
_database_code_depnum_ccdc_archive 'CCDC 740931'
#TrackingRef 'CCDC740931_Revision.cif'

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C42 H60 Cu2 N4 O16 P4, 4(H2 O)'
_chemical_formula_sum            'C42 H68 Cu2 N4 O20 P4'
_chemical_formula_weight         1199.96

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'
P P 0.1023 0.0942 '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'
_symmetry_space_group_name_Hall  '-P 1'

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

_cell_length_a                   9.871(3)
_cell_length_b                   11.180(4)
_cell_length_c                   14.456(5)
_cell_angle_alpha                105.683(5)
_cell_angle_beta                 101.778(6)
_cell_angle_gamma                104.361(5)
_cell_volume                     1423.6(8)
_cell_formula_units_Z            1
_cell_measurement_temperature    298(2)
_cell_measurement_reflns_used    1779
_cell_measurement_theta_min      2.8
_cell_measurement_theta_max      22.0

_exptl_crystal_description       block
_exptl_crystal_colour            blue
_exptl_crystal_size_max          0.30
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.20
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.400
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             626
_exptl_absorpt_coefficient_mu    0.931
_exptl_absorpt_correction_T_min  0.7676
_exptl_absorpt_correction_T_max  0.8357
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS; Sheldrick, 2000'

_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, Bruker'
_diffrn_measurement_method       '\w scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         0
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            7266
_diffrn_reflns_av_R_equivalents  0.0703
_diffrn_reflns_av_sigmaI/netI    0.1133
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_theta_min         1.53
_diffrn_reflns_theta_max         25.00
_reflns_number_total             4922
_reflns_number_gt                2756
_reflns_threshold_expression     I>2\s(I)

_computing_data_collection       'SMART (Bruker,2000)'
_computing_cell_refinement       'SAINT (Bruker,2000)'
_computing_data_reduction        SAINT
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1997)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    'SHELXTL/PC (Sheldrick, 1999)'
_computing_publication_material  SHELXTL/PC

_refine_special_details          
;
Structure was phased by direct methods. The space group choice was
confirmed by successful convergence of the full-matrix least-squares
refinement on F^2^.

Fourier maps show that there were severe partial occupancies for two
ethyl groups and one water molecule. The occupancies of these sites
were freely refined with PART instruction, and then C11A , C11B ,
C12A , and C12B were fixed. The final occupancies of all
disorder atoms from the refinement were C11A 0.34, C11B 0.66,
C12A 0.34, C12B 0.66; C20A 0.53(2), C21A 0.53(2), C20B 0.47(2),
C21B 0.47(2); O9A 0.716(13), O9B 0.284(13), respectively.
The ethyl group had still large Ueq values.
This should be results of severe disordered
side-chains (ethyl group). H-atoms except water were included in
calculated positions and treated as riding atoms using the SHELXL
default parameters. H atoms attached to O(water) were located in difference
Fourier maps and their global Uiso values were refined.

Displacement parameters for the proposed model converged with an unusually
large Ueq(max)/Ueq(min) ratio 5.78 for C and 7.19 for H. This large range may
be attributed to the basic structural network which might best be described as
severe systematic disorder for side-chains (ethyl group).
In particular the disordered side-chains are very dynamic.

Structure contains solvent accessible voids of 65.8 A3/per unit cell, i.e.
some 4.6% of the total volume. Data were corrected for disordered electron
density through use of the SQUEEZE procedure. Attempts to refine peaks of
residual electron density as solvent water molecules were unsuccessful.
Derived values (formula weight, density, absorption coefficient) do not
contain the contribution of the disordered solvent molecule.

ISOR instruction was employed to have ellipsoids of sites
(C11A C11B C12A C12B C20A C20B C21A C21B O10 C16 C17 C18)
be restraint to more appropriate values. So, 72 restraints were used
for refinement anisotropically. 4 restraints were used for refinement to fix
disordered ethyl chains binding to O7 and O3.
;

_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^)+(0.0870P)^2^] 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         4922
_refine_ls_number_parameters     377
_refine_ls_number_restraints     76
_refine_ls_R_factor_all          0.1137
_refine_ls_R_factor_gt           0.0632
_refine_ls_wR_factor_ref         0.1742
_refine_ls_wR_factor_gt          0.1520
_refine_ls_goodness_of_fit_ref   0.930
_refine_ls_restrained_S_all      0.944
_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 0.05416(7) 0.18118(6) 0.43176(5) 0.0419(3) Uani 1 1 d . . .
N1 N 0.1527(5) 0.2685(4) 0.5814(3) 0.0443(12) Uani 1 1 d . A .
H1 H 0.1407 0.3489 0.5987 0.053 Uiso 1 1 d R . .
N2 N 0.2174(5) 0.2869(4) 0.3927(3) 0.0408(11) Uani 1 1 d . B .
H2 H 0.2085 0.3681 0.4023 0.049 Uiso 1 1 d R . .
O1 O -0.1203(4) 0.0983(4) 0.4641(3) 0.0517(10) Uani 1 1 d . . .
O2 O 0.1507(4) 0.0221(3) 0.4103(3) 0.0507(10) Uani 1 1 d . . .
O3 O -0.2055(4) 0.1901(4) 0.6081(3) 0.0592(12) Uani 1 1 d . . .
O4 O 0.0564(5) 0.4514(4) 0.7008(3) 0.0606(12) Uani 1 1 d . A .
H4 H 0.0839 0.5317 0.7253 0.091 Uiso 1 1 calc R . .
O5 O -0.0722(4) 0.1316(4) 0.2939(3) 0.0543(11) Uani 1 1 d . . .
O6 O -0.0304(5) 0.3205(4) 0.2247(3) 0.0706(13) Uani 1 1 d . . .
O7 O -0.0446(5) 0.0950(4) 0.1221(3) 0.0613(12) Uani 1 1 d . . .
O8 O 0.4160(6) 0.1299(7) 0.2509(5) 0.105(2) Uani 1 1 d . B .
H8 H 0.4680 0.0942 0.2241 0.157 Uiso 1 1 calc R . .
P1 P -0.11039(16) 0.10356(14) 0.57032(12) 0.0443(4) Uani 1 1 d . . .
P2 P -0.00153(17) 0.19843(14) 0.22908(12) 0.0468(4) Uani 1 1 d . B .
C1 C 0.3134(6) 0.2922(6) 0.6131(5) 0.0521(16) Uani 1 1 d . . .
H1A H 0.3311 0.2084 0.5984 0.063 Uiso 1 1 calc R . .
H1B H 0.3512 0.3368 0.6852 0.063 Uiso 1 1 calc R . .
C2 C 0.3942(7) 0.3727(6) 0.5618(5) 0.0581(17) Uani 1 1 d . . .
H2A H 0.4982 0.3986 0.5943 0.070 Uiso 1 1 calc R . .
H2B H 0.3675 0.4520 0.5703 0.070 Uiso 1 1 calc R . .
C3 C 0.3648(6) 0.3031(6) 0.4518(4) 0.0505(15) Uani 1 1 d . . .
H3A H 0.4363 0.3524 0.4273 0.061 Uiso 1 1 calc R . .
H3B H 0.3765 0.2173 0.4421 0.061 Uiso 1 1 calc R . .
C4 C 0.0802(6) 0.1949(5) 0.6408(4) 0.0398(13) Uani 1 1 d . . .
H4A H 0.1279 0.1285 0.6448 0.048 Uiso 1 1 calc R A .
C5 C 0.1043(6) 0.2776(5) 0.7486(4) 0.0448(14) Uani 1 1 d . A .
C6 C 0.0878(6) 0.4001(6) 0.7743(5) 0.0466(14) Uani 1 1 d . . .
C7 C 0.1045(7) 0.4666(7) 0.8748(5) 0.0655(19) Uani 1 1 d . A .
H7 H 0.0938 0.5494 0.8928 0.079 Uiso 1 1 calc R . .
C8 C 0.1361(9) 0.4126(7) 0.9466(5) 0.077(2) Uani 1 1 d . . .
H8A H 0.1483 0.4587 1.0134 0.093 Uiso 1 1 calc R A .
C9 C 0.1501(10) 0.2896(8) 0.9203(6) 0.089(3) Uani 1 1 d . A .
H9 H 0.1695 0.2514 0.9691 0.107 Uiso 1 1 calc R . .
C10 C 0.1357(7) 0.2239(6) 0.8235(5) 0.0620(18) Uani 1 1 d . . .
H10 H 0.1469 0.1412 0.8067 0.074 Uiso 1 1 calc R A .
C11A C -0.271(2) 0.1656(19) 0.6875(17) 0.045(5) Uani 0.34 1 d PDU A 1
H11A H -0.2287 0.1124 0.7200 0.032 Uiso 0.34 1 d PR A 1
H11B H -0.2647 0.2468 0.7368 0.032 Uiso 0.34 1 d PR A 1
C12A C -0.421(3) 0.089(5) 0.618(4) 0.23(2) Uani 0.34 1 d PDU A 1
H12A H -0.4380 -0.0039 0.6006 0.163 Uiso 0.34 1 d PR A 1
H12B H -0.4305 0.1114 0.5577 0.163 Uiso 0.34 1 d PR A 1
H12C H -0.4920 0.1117 0.6495 0.163 Uiso 0.34 1 d PR A 1
C11B C -0.322(3) 0.146(2) 0.6450(17) 0.149(8) Uani 0.66 1 d PDU A -1
H11C H -0.4138 0.1299 0.5960 0.149 Uiso 0.66 1 d PR A -1
H11D H -0.3221 0.0643 0.6558 0.149 Uiso 0.66 1 d PR A -1
C12B C -0.300(3) 0.241(3) 0.7470(17) 0.230(11) Uani 0.66 1 d PDU A -1
H12D H -0.2286 0.2363 0.8010 0.230 Uiso 0.66 1 d PR A -1
H12E H -0.3936 0.2218 0.7594 0.230 Uiso 0.66 1 d PR A -1
H12F H -0.2720 0.3273 0.7428 0.230 Uiso 0.66 1 d PR A -1
C13 C 0.1910(6) 0.2235(6) 0.2822(4) 0.0467(15) Uani 1 1 d . . .
H13 H 0.1983 0.1355 0.2738 0.056 Uiso 1 1 calc R B .
C14 C 0.2979(7) 0.2843(7) 0.2376(4) 0.0585(17) Uani 1 1 d . B .
C15 C 0.4127(8) 0.2349(9) 0.2235(6) 0.077(2) Uani 1 1 d . . .
C16 C 0.5181(10) 0.2947(11) 0.1850(7) 0.107(3) Uani 1 1 d U B .
H16 H 0.5954 0.2630 0.1782 0.129 Uiso 1 1 calc R . .
C17 C 0.5077(11) 0.3980(12) 0.1579(7) 0.104(3) Uani 1 1 d U . .
H17 H 0.5735 0.4319 0.1264 0.125 Uiso 1 1 calc R B .
C18 C 0.4042(11) 0.4557(9) 0.1748(6) 0.098(3) Uani 1 1 d U B .
H18 H 0.4050 0.5322 0.1606 0.118 Uiso 1 1 calc R . .
C19 C 0.2974(8) 0.3984(8) 0.2135(5) 0.080(2) Uani 1 1 d . . .
H19 H 0.2249 0.4356 0.2236 0.096 Uiso 1 1 calc R B .
C20A C -0.140(2) 0.0906(19) 0.0286(15) 0.083(6) Uani 0.50(2) 1 d PDU B 1
H20A H -0.1223 0.0372 -0.0297 0.083 Uiso 0.50(2) 1 calc PR B 1
H20B H -0.1289 0.1779 0.0252 0.083 Uiso 0.50(2) 1 calc PR B 1
C21A C -0.289(2) 0.029(3) 0.037(2) 0.138(10) Uani 0.50(2) 1 d PDU B 1
H21A H -0.3020 -0.0613 0.0306 0.138 Uiso 0.50(2) 1 calc PR B 1
H21B H -0.3624 0.0334 -0.0155 0.138 Uiso 0.50(2) 1 calc PR B 1
H21C H -0.2967 0.0748 0.1010 0.138 Uiso 0.50(2) 1 calc PR B 1
O9A O 0.2166(7) 0.5670(6) 0.4599(5) 0.076(3) Uani 0.723(13) 1 d P C 1
H9A H 0.2320 0.6532 0.4769 0.076 Uiso 0.723(13) 1 d PR C 1
H9C H 0.1629 0.5282 0.3988 0.076 Uiso 0.723(13) 1 d PR C 1
C20B C -0.073(2) 0.129(3) 0.041(2) 0.121(9) Uani 0.50(2) 1 d PDU B 2
H20C H -0.0306 0.0835 -0.0067 0.121 Uiso 0.50(2) 1 calc PR B 2
H20D H -0.0219 0.2222 0.0602 0.121 Uiso 0.50(2) 1 calc PR B 2
C21B C -0.229(3) 0.104(3) -0.013(2) 0.172(13) Uani 0.50(2) 1 d PDU B 2
H21D H -0.2816 0.0117 -0.0352 0.172 Uiso 0.50(2) 1 calc PR B 2
H21E H -0.2341 0.1332 -0.0696 0.172 Uiso 0.50(2) 1 calc PR B 2
H21F H -0.2730 0.1509 0.0320 0.172 Uiso 0.50(2) 1 calc PR B 2
O9B O 0.199(2) 0.6279(17) 0.5494(14) 0.080(8) Uani 0.277(13) 1 d P C 2
H9B H 0.2344 0.5985 0.5024 0.080 Uiso 0.277(13) 1 d PR C 2
H9D H 0.2342 0.6078 0.5998 0.080 Uiso 0.277(13) 1 d PR C 2
O10 O 0.6311(10) 0.0243(10) 0.2572(9) 0.221(4) Uani 1 1 d U . .
H10B H 0.7034 0.0591 0.2387 0.331 Uiso 1 1 d R . .
H10A H 0.6619 0.0334 0.3191 0.331 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 0.0411(4) 0.0343(4) 0.0482(5) 0.0112(3) 0.0114(3) 0.0129(3)
N1 0.043(3) 0.031(2) 0.056(3) 0.008(2) 0.016(2) 0.013(2)
N2 0.043(3) 0.030(2) 0.043(3) 0.008(2) 0.007(2) 0.011(2)
O1 0.041(2) 0.057(3) 0.048(3) 0.013(2) 0.0068(19) 0.0113(19)
O2 0.052(2) 0.034(2) 0.072(3) 0.019(2) 0.026(2) 0.0171(18)
O3 0.056(3) 0.046(2) 0.088(3) 0.021(2) 0.035(2) 0.030(2)
O4 0.098(3) 0.038(2) 0.052(3) 0.012(2) 0.020(2) 0.037(2)
O5 0.042(2) 0.065(3) 0.057(3) 0.025(2) 0.014(2) 0.0130(19)
O6 0.087(3) 0.041(2) 0.078(3) 0.011(2) 0.005(3) 0.037(2)
O7 0.078(3) 0.052(3) 0.045(3) 0.004(2) 0.004(2) 0.032(2)
O8 0.077(4) 0.113(5) 0.130(5) 0.022(4) 0.046(4) 0.045(4)
P1 0.0467(9) 0.0321(8) 0.0567(11) 0.0125(7) 0.0192(8) 0.0162(7)
P2 0.0506(9) 0.0367(9) 0.0485(10) 0.0064(7) 0.0082(8) 0.0203(7)
C1 0.041(4) 0.052(4) 0.053(4) 0.014(3) 0.008(3) 0.007(3)
C2 0.046(4) 0.055(4) 0.056(4) 0.015(3) 0.001(3) 0.003(3)
C3 0.038(3) 0.052(4) 0.057(4) 0.020(3) 0.009(3) 0.008(3)
C4 0.044(3) 0.029(3) 0.047(4) 0.015(3) 0.010(3) 0.013(2)
C5 0.055(4) 0.033(3) 0.048(4) 0.014(3) 0.015(3) 0.015(3)
C6 0.051(4) 0.046(4) 0.046(4) 0.015(3) 0.019(3) 0.017(3)
C7 0.075(5) 0.065(4) 0.055(4) 0.008(4) 0.016(4) 0.036(4)
C8 0.115(7) 0.076(5) 0.044(4) 0.012(4) 0.022(4) 0.047(5)
C9 0.133(7) 0.087(6) 0.061(5) 0.030(5) 0.029(5) 0.055(5)
C10 0.084(5) 0.054(4) 0.054(4) 0.016(4) 0.024(4) 0.031(4)
C11A 0.051(8) 0.041(8) 0.054(9) 0.003(6) 0.039(7) 0.026(6)
C12A 0.23(2) 0.23(2) 0.23(2) 0.079(7) 0.068(6) 0.075(7)
C11B 0.165(12) 0.132(11) 0.152(12) 0.058(9) 0.034(9) 0.051(9)
C12B 0.231(14) 0.231(14) 0.230(14) 0.079(10) 0.084(10) 0.061(10)
C13 0.042(3) 0.046(3) 0.050(4) 0.012(3) 0.014(3) 0.015(3)
C14 0.062(4) 0.061(4) 0.038(4) 0.009(3) 0.013(3) 0.005(3)
C15 0.061(5) 0.084(6) 0.073(5) 0.014(5) 0.023(4) 0.013(4)
C16 0.081(5) 0.125(7) 0.095(6) 0.009(5) 0.042(5) 0.015(5)
C17 0.088(6) 0.128(7) 0.067(5) 0.022(5) 0.028(4) -0.008(5)
C18 0.109(6) 0.092(6) 0.068(5) 0.040(4) 0.007(5) -0.010(5)
C19 0.067(5) 0.091(6) 0.050(4) 0.025(4) -0.002(4) -0.015(4)
C20A 0.071(9) 0.083(10) 0.083(9) 0.004(7) 0.001(7) 0.048(8)
C21A 0.139(13) 0.141(13) 0.131(13) 0.033(8) 0.034(8) 0.058(9)
O9A 0.106(6) 0.044(4) 0.067(6) 0.006(3) -0.004(4) 0.041(4)
C20B 0.135(13) 0.112(12) 0.118(12) 0.030(8) 0.044(10) 0.045(9)
C21B 0.166(15) 0.166(15) 0.173(15) 0.057(10) 0.032(10) 0.052(10)
O9B 0.131(16) 0.081(14) 0.064(15) 0.044(12) 0.033(11) 0.070(12)
O10 0.164(7) 0.223(8) 0.286(9) 0.068(6) 0.079(6) 0.088(6)

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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Cu1 O1 1.953(4) . ?
Cu1 O5 1.970(4) . ?
Cu1 N2 2.025(4) . ?
Cu1 N1 2.026(5) . ?
Cu1 O2 2.198(4) . ?
N1 C1 1.492(7) . ?
N1 C4 1.507(7) . ?
N1 H1 0.9100 . ?
N2 C3 1.469(7) . ?
N2 C13 1.499(7) . ?
N2 H2 0.9100 . ?
O1 P1 1.502(4) . ?
O2 P1 1.480(4) 2_556 ?
O3 C11B 1.40(3) . ?
O3 C11A 1.48(2) . ?
O3 P1 1.577(4) . ?
O4 C6 1.356(7) . ?
O4 H4 0.8200 . ?
O5 P2 1.520(4) . ?
O6 P2 1.477(4) . ?
O7 C20B 1.33(3) . ?
O7 C20A 1.46(2) . ?
O7 P2 1.559(4) . ?
O8 C15 1.341(10) . ?
O8 H8 0.8200 . ?
P1 O2 1.480(4) 2_556 ?
P1 C4 1.822(5) . ?
P2 C13 1.818(6) . ?
C1 C2 1.498(8) . ?
C1 H1A 0.9700 . ?
C1 H1B 0.9700 . ?
C2 C3 1.500(8) . ?
C2 H2A 0.9700 . ?
C2 H2B 0.9700 . ?
C3 H3A 0.9700 . ?
C3 H3B 0.9700 . ?
C4 C5 1.517(8) . ?
C4 H4A 0.9800 . ?
C5 C6 1.378(8) . ?
C5 C10 1.392(8) . ?
C6 C7 1.396(8) . ?
C7 C8 1.356(9) . ?
C7 H7 0.9300 . ?
C8 C9 1.374(10) . ?
C8 H8A 0.9300 . ?
C9 C10 1.352(9) . ?
C9 H9 0.9300 . ?
C10 H10 0.9300 . ?
C11A C12A 1.5001(12) . ?
C11A H11A 0.9700 . ?
C11A H11B 0.9700 . ?
C12A C11B 0.96(3) . ?
C12A H12A 0.9600 . ?
C12A H12B 0.9600 . ?
C12A H12C 0.9600 . ?
C11B C12B 1.4999(12) . ?
C11B H11C 0.9700 . ?
C11B H11D 0.9700 . ?
C12B H12D 0.9600 . ?
C12B H12E 0.9600 . ?
C12B H12F 0.9600 . ?
C13 C14 1.466(8) . ?
C13 H13 0.9800 . ?
C14 C15 1.405(10) . ?
C14 C19 1.411(10) . ?
C15 C16 1.390(12) . ?
C16 C17 1.335(13) . ?
C16 H16 0.9300 . ?
C17 C18 1.366(14) . ?
C17 H17 0.9300 . ?
C18 C19 1.390(10) . ?
C18 H18 0.9300 . ?
C19 H19 0.9300 . ?
C20A C21A 1.4998(11) . ?
C20A H20A 0.9700 . ?
C20A H20B 0.9700 . ?
C21A H21A 0.9600 . ?
C21A H21B 0.9600 . ?
C21A H21C 0.9600 . ?
O9A H9A 0.8934 . ?
O9A H9C 0.8593 . ?
O9A H9B 0.5834 . ?
C20B C21B 1.5000(12) . ?
C20B H20C 0.9700 . ?
C20B H20D 0.9700 . ?
C21B H21D 0.9600 . ?
C21B H21E 0.9600 . ?
C21B H21F 0.9600 . ?
O9B H9A 1.2403 . ?
O9B H9B 0.8489 . ?
O9B H9D 0.8497 . ?
O10 H10B 0.8540 . ?
O10 H10A 0.8531 . ?

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 O5 87.10(16) . . ?
O1 Cu1 N2 170.67(16) . . ?
O5 Cu1 N2 88.38(17) . . ?
O1 Cu1 N1 87.71(17) . . ?
O5 Cu1 N1 163.80(17) . . ?
N2 Cu1 N1 94.43(17) . . ?
O1 Cu1 O2 99.81(15) . . ?
O5 Cu1 O2 99.31(16) . . ?
N2 Cu1 O2 88.98(16) . . ?
N1 Cu1 O2 96.70(16) . . ?
C1 N1 C4 109.7(4) . . ?
C1 N1 Cu1 115.0(3) . . ?
C4 N1 Cu1 111.7(3) . . ?
C1 N1 H1 106.3 . . ?
C4 N1 H1 107.0 . . ?
Cu1 N1 H1 106.6 . . ?
C3 N2 C13 112.5(4) . . ?
C3 N2 Cu1 114.2(3) . . ?
C13 N2 Cu1 107.3(3) . . ?
C3 N2 H2 107.9 . . ?
C13 N2 H2 107.1 . . ?
Cu1 N2 H2 107.5 . . ?
P1 O1 Cu1 119.6(2) . . ?
P1 O2 Cu1 130.8(2) 2_556 . ?
C11B O3 P1 123.6(11) . . ?
C11A O3 P1 117.8(8) . . ?
C6 O4 H4 109.5 . . ?
P2 O5 Cu1 114.0(2) . . ?
C20B O7 P2 120.7(13) . . ?
C20A O7 P2 128.3(8) . . ?
C15 O8 H8 109.5 . . ?
O2 P1 O1 118.1(2) 2_556 . ?
O2 P1 O3 110.9(2) 2_556 . ?
O1 P1 O3 106.3(2) . . ?
O2 P1 C4 108.5(2) 2_556 . ?
O1 P1 C4 104.9(2) . . ?
O3 P1 C4 107.5(2) . . ?
O6 P2 O5 116.7(3) . . ?
O6 P2 O7 111.5(3) . . ?
O5 P2 O7 107.8(2) . . ?
O6 P2 C13 112.8(3) . . ?
O5 P2 C13 102.2(3) . . ?
O7 P2 C13 104.7(2) . . ?
N1 C1 C2 112.7(5) . . ?
N1 C1 H1A 109.1 . . ?
C2 C1 H1A 109.1 . . ?
N1 C1 H1B 109.1 . . ?
C2 C1 H1B 109.1 . . ?
H1A C1 H1B 107.8 . . ?
C1 C2 C3 114.0(5) . . ?
C1 C2 H2A 108.8 . . ?
C3 C2 H2A 108.8 . . ?
C1 C2 H2B 108.8 . . ?
C3 C2 H2B 108.8 . . ?
H2A C2 H2B 107.6 . . ?
N2 C3 C2 112.6(5) . . ?
N2 C3 H3A 109.1 . . ?
C2 C3 H3A 109.1 . . ?
N2 C3 H3B 109.1 . . ?
C2 C3 H3B 109.1 . . ?
H3A C3 H3B 107.8 . . ?
N1 C4 C5 114.2(4) . . ?
N1 C4 P1 110.0(3) . . ?
C5 C4 P1 114.7(4) . . ?
N1 C4 H4A 105.7 . . ?
C5 C4 H4A 105.7 . . ?
P1 C4 H4A 105.7 . . ?
C6 C5 C10 118.9(5) . . ?
C6 C5 C4 122.7(5) . . ?
C10 C5 C4 118.3(5) . . ?
O4 C6 C5 118.6(5) . . ?
O4 C6 C7 122.5(5) . . ?
C5 C6 C7 118.9(6) . . ?
C8 C7 C6 121.1(6) . . ?
C8 C7 H7 119.4 . . ?
C6 C7 H7 119.4 . . ?
C7 C8 C9 119.8(7) . . ?
C7 C8 H8A 120.1 . . ?
C9 C8 H8A 120.1 . . ?
C10 C9 C8 120.1(7) . . ?
C10 C9 H9 120.0 . . ?
C8 C9 H9 120.0 . . ?
C9 C10 C5 121.2(6) . . ?
C9 C10 H10 119.4 . . ?
C5 C10 H10 119.4 . . ?
O3 C11A C12A 95(3) . . ?
O3 C11A H11A 112.6 . . ?
C12A C11A H11A 111.6 . . ?
O3 C11A H11B 111.6 . . ?
C12A C11A H11B 114.4 . . ?
H11A C11A H11B 110.6 . . ?
O3 C11A H11D 100.1 . . ?
C12A C11A H11D 50.1 . . ?
H12A C12A H12B 109.5 . . ?
H12A C12A H12C 109.5 . . ?
H12B C12A H12C 109.5 . . ?
O3 C11B C12B 109.8(19) . . ?
O3 C11B H11C 109.6 . . ?
C12B C11B H11C 114.8 . . ?
O3 C11B H11D 109.8 . . ?
C12B C11B H11D 104.9 . . ?
H11C C11B H11D 107.7 . . ?
C11B C12B H12E 105.9 . . ?
H12D C12B H12E 109.5 . . ?
C11B C12B H12F 106.9 . . ?
H12D C12B H12F 109.5 . . ?
H12E C12B H12F 109.5 . . ?
C14 C13 N2 116.5(5) . . ?
C14 C13 P2 119.2(5) . . ?
N2 C13 P2 103.6(3) . . ?
C14 C13 H13 105.5 . . ?
N2 C13 H13 105.5 . . ?
P2 C13 H13 105.5 . . ?
C15 C14 C19 117.0(7) . . ?
C15 C14 C13 120.3(7) . . ?
C19 C14 C13 122.6(7) . . ?
O8 C15 C16 122.5(9) . . ?
O8 C15 C14 116.6(7) . . ?
C16 C15 C14 120.9(9) . . ?
C17 C16 C15 119.7(10) . . ?
C17 C16 H16 120.1 . . ?
C15 C16 H16 120.1 . . ?
C16 C17 C18 122.4(10) . . ?
C16 C17 H17 118.8 . . ?
C18 C17 H17 118.8 . . ?
C17 C18 C19 119.0(9) . . ?
C17 C18 H18 120.5 . . ?
C19 C18 H18 120.5 . . ?
C18 C19 C14 120.7(9) . . ?
C18 C19 H19 119.6 . . ?
C14 C19 H19 119.6 . . ?
O7 C20A C21A 101.7(15) . . ?
O7 C20A H20A 111.4 . . ?
C21A C20A H20A 111.4 . . ?
O7 C20A H20B 111.4 . . ?
C21A C20A H20B 111.4 . . ?
H20A C20A H20B 109.3 . . ?
H9A O9A H9C 109.7 . . ?
O7 C20B C21B 118(2) . . ?
O7 C20B H20C 107.8 . . ?
C21B C20B H20C 107.8 . . ?
O7 C20B H20D 107.8 . . ?
C21B C20B H20D 107.8 . . ?
H20C C20B H20D 107.1 . . ?
C20B C21B H21D 109.5 . . ?
C20B C21B H21E 109.5 . . ?
H21D C21B H21E 109.5 . . ?
C20B C21B H21F 109.5 . . ?
H21D C21B H21F 109.5 . . ?
H21E C21B H21F 109.5 . . ?
H9B O9B H9D 109.0 . . ?
H10B O10 H10A 108.5 . . ?

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 C1 148.2(4) . . . . ?
O5 Cu1 N1 C1 -140.4(6) . . . . ?
N2 Cu1 N1 C1 -40.9(4) . . . . ?
O2 Cu1 N1 C1 48.6(4) . . . . ?
O1 Cu1 N1 C4 22.3(3) . . . . ?
O5 Cu1 N1 C4 93.7(7) . . . . ?
N2 Cu1 N1 C4 -166.8(3) . . . . ?
O2 Cu1 N1 C4 -77.3(3) . . . . ?
O5 Cu1 N2 C3 -153.4(4) . . . . ?
N1 Cu1 N2 C3 42.5(4) . . . . ?
O2 Cu1 N2 C3 -54.1(4) . . . . ?
O5 Cu1 N2 C13 -28.1(3) . . . . ?
N1 Cu1 N2 C13 167.9(3) . . . . ?
O2 Cu1 N2 C13 71.3(3) . . . . ?
O5 Cu1 O1 P1 -176.5(3) . . . . ?
N1 Cu1 O1 P1 -11.9(3) . . . . ?
O2 Cu1 O1 P1 84.5(3) . . . . ?
O1 Cu1 O2 P1 -8.5(3) . . . 2_556 ?
O5 Cu1 O2 P1 -97.1(3) . . . 2_556 ?
N2 Cu1 O2 P1 174.7(3) . . . 2_556 ?
N1 Cu1 O2 P1 80.4(3) . . . 2_556 ?
O1 Cu1 O5 P2 167.0(3) . . . . ?
N2 Cu1 O5 P2 -4.8(3) . . . . ?
N1 Cu1 O5 P2 95.5(6) . . . . ?
O2 Cu1 O5 P2 -93.5(3) . . . . ?
Cu1 O1 P1 O2 -120.9(3) . . . 2_556 ?
Cu1 O1 P1 O3 113.9(3) . . . . ?
Cu1 O1 P1 C4 0.1(3) . . . . ?
C11B O3 P1 O2 -6.2(13) . . . 2_556 ?
C11A O3 P1 O2 23.4(10) . . . 2_556 ?
C11B O3 P1 O1 123.3(13) . . . . ?
C11A O3 P1 O1 152.9(9) . . . . ?
C11B O3 P1 C4 -124.7(13) . . . . ?
C11A O3 P1 C4 -95.1(10) . . . . ?
Cu1 O5 P2 O6 -94.1(3) . . . . ?
Cu1 O5 P2 O7 139.6(2) . . . . ?
Cu1 O5 P2 C13 29.5(3) . . . . ?
C20B O7 P2 O6 13.0(13) . . . . ?
C20A O7 P2 O6 -18.1(11) . . . . ?
C20B O7 P2 O5 142.4(12) . . . . ?
C20A O7 P2 O5 111.3(11) . . . . ?
C20B O7 P2 C13 -109.3(12) . . . . ?
C20A O7 P2 C13 -140.4(11) . . . . ?
C4 N1 C1 C2 -176.3(4) . . . . ?
Cu1 N1 C1 C2 56.7(6) . . . . ?
N1 C1 C2 C3 -69.2(7) . . . . ?
C13 N2 C3 C2 177.1(5) . . . . ?
Cu1 N2 C3 C2 -60.3(5) . . . . ?
C1 C2 C3 N2 71.7(7) . . . . ?
C1 N1 C4 C5 74.5(6) . . . . ?
Cu1 N1 C4 C5 -156.7(4) . . . . ?
C1 N1 C4 P1 -154.8(4) . . . . ?
Cu1 N1 C4 P1 -26.0(4) . . . . ?
O2 P1 C4 N1 144.0(3) 2_556 . . . ?
O1 P1 C4 N1 17.0(4) . . . . ?
O3 P1 C4 N1 -96.0(4) . . . . ?
O2 P1 C4 C5 -85.6(4) 2_556 . . . ?
O1 P1 C4 C5 147.3(4) . . . . ?
O3 P1 C4 C5 34.4(5) . . . . ?
N1 C4 C5 C6 46.7(7) . . . . ?
P1 C4 C5 C6 -81.5(6) . . . . ?
N1 C4 C5 C10 -137.3(6) . . . . ?
P1 C4 C5 C10 94.5(6) . . . . ?
C10 C5 C6 O4 -179.6(6) . . . . ?
C4 C5 C6 O4 -3.6(8) . . . . ?
C10 C5 C6 C7 0.6(9) . . . . ?
C4 C5 C6 C7 176.6(6) . . . . ?
O4 C6 C7 C8 -179.9(7) . . . . ?
C5 C6 C7 C8 -0.1(10) . . . . ?
C6 C7 C8 C9 -0.9(12) . . . . ?
C7 C8 C9 C10 1.5(13) . . . . ?
C8 C9 C10 C5 -1.0(12) . . . . ?
C6 C5 C10 C9 0.0(10) . . . . ?
C4 C5 C10 C9 -176.2(6) . . . . ?
P1 O3 C11A C12A -102(3) . . . . ?
P1 O3 C11B C12B 125.9(17) . . . . ?
C3 N2 C13 C14 -53.3(7) . . . . ?
Cu1 N2 C13 C14 -179.6(5) . . . . ?
C3 N2 C13 P2 173.8(4) . . . . ?
Cu1 N2 C13 P2 47.4(4) . . . . ?
O6 P2 C13 C14 -55.2(5) . . . . ?
O5 P2 C13 C14 178.6(5) . . . . ?
O7 P2 C13 C14 66.2(5) . . . . ?
O6 P2 C13 N2 76.1(4) . . . . ?
O5 P2 C13 N2 -50.1(4) . . . . ?
O7 P2 C13 N2 -162.5(3) . . . . ?
N2 C13 C14 C15 96.8(7) . . . . ?
P2 C13 C14 C15 -137.8(6) . . . . ?
N2 C13 C14 C19 -78.8(7) . . . . ?
P2 C13 C14 C19 46.6(7) . . . . ?
C19 C14 C15 O8 177.1(6) . . . . ?
C13 C14 C15 O8 1.3(10) . . . . ?
C19 C14 C15 C16 -1.6(10) . . . . ?
C13 C14 C15 C16 -177.4(6) . . . . ?
O8 C15 C16 C17 179.1(8) . . . . ?
C14 C15 C16 C17 -2.2(13) . . . . ?
C15 C16 C17 C18 6.1(14) . . . . ?
C16 C17 C18 C19 -5.8(14) . . . . ?
C17 C18 C19 C14 1.7(11) . . . . ?
C15 C14 C19 C18 1.8(9) . . . . ?
C13 C14 C19 C18 177.6(6) . . . . ?
C20B O7 C20A C21A -165(5) . . . . ?
P2 O7 C20A C21A -81.9(15) . . . . ?
C20A O7 C20B C21B 18(2) . . . . ?
P2 O7 C20B C21B -98(2) . . . . ?

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
N1 H1 O4 0.91 2.06 2.792(6) 136.5 .
N2 H2 O9A 0.91 2.13 3.020(7) 166.5 .
O4 H4 O6 0.82 1.86 2.584(5) 146.0 2_566
O8 H8 O10 0.82 1.99 2.671(11) 140.6 .
O9A H9C O4 0.86 2.44 3.101(7) 134.0 2_566
O9A H9A O3 0.89 2.43 3.147(7) 137.6 2_566
O10 H10B O5 0.85 2.06 2.753(10) 137.9 1_655
O10 H10A O1 0.85 2.47 3.211(12) 145.5 1_655

_diffrn_measured_fraction_theta_max 0.980
_diffrn_reflns_theta_full        25.00
_diffrn_measured_fraction_theta_full 0.980
_refine_diff_density_max         0.955
_refine_diff_density_min         -0.524
_refine_diff_density_rms         0.087