Supplementary Material (ESI) for Dalton Transactions
This journal is © The Royal Society of Chemistry 2005

data_global
_journal_name_full               'Dalton Trans.'

_journal_coden_Cambridge         0222

_publ_contact_author_name        'Jan Reedijk'
_publ_contact_author_address     
;
Leiden Institute of Chemistry,
Gorlaeus Laboratories,
Leiden University,
PO Box 9502,
2300 RA Leiden,
The Netherlands.
;

_publ_contact_author_email       reedijk@chem.leidenuniv.nl
_publ_contact_author_fax         '(+31) 71 527 4671'
_publ_section_title              
;
Selective copper(II)-mediated oxidative coupling of a nucleophilic reagent to
the para-methyl group of 2,4,6-trimethylphenol
;

loop_
_publ_author_name
_publ_author_address
'Christophe Boldron'
; Leiden Institute of Chemistry,
Gorlaeus Laboratories,
Leiden University,
PO Box 9502,
2300 RA Leiden,
The Netherlands.
;
'Patrick Gamez'
; Leiden Institute of Chemistry,
Gorlaeus Laboratories,
Leiden University,
PO Box 9502,
2300 RA Leiden,
The Netherlands.
;
'Duncan M. Tooke'
; Department of Crystal and Structural Chemistry,
Utrecht University,
Padualaan 8,
3584 CH Utrecht,
The Netherlands.
;
'Anthony L. Spek'
; Department of Crystal and Structural Chemistry,
Utrecht University,
Padualaan 8,
3584 CH Utrecht,
The Netherlands.
;
'Jan Reedijk'
; Leiden Institute of Chemistry,
Gorlaeus Laboratories,
Leiden University,
PO Box 9502,
2300 RA Leiden,
The Netherlands.
;

_publ_section_references         
;
Beurskens, P.T., Beurskens, G, de Gelder, R., Garcia-Granda, S., Gould, R.O.,
Israel, R., and Smits, J.M.M. (1999). The DIRDIF-99 program system,
Crystallography Laboratory, University of Nijmegen, The Netherlands.

Duisenberg, A.J.M. (1992). J. Appl. Cryst. 25, 92-96.

Duisenberg, A.J.M., Kroon-Batenburg, L.M.J. & Schreurs, A.M.M. (2003).
J. Appl. Cryst. 36, 220-229.

Hooft, R.W.W. (1998), Nonius Collect Software, Nonius B.V., Delft, The
Netherlands.

Sheldrick (1986), G.M. SHELXS86. Program for crystal structure
solution. University of Gottingen, Germany.

Sheldrick (1997), G.M. SHELXL97. Program for crystal structure
refinement. University of Gottingen, Germany.

Sheldrick (2004), G.M. SADABS. Program for Absorption Correction,
Bruker AXS, Karlsruhr, Germany.

Spek, A.L. (2003). J. Appl. Cryst. 36, 7-13.
;

data_1
_database_code_depnum_ccdc_archive 'CCDC 258045'

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C35 H27 Cl2 Cu2 F5 N4 O2, 0.8(C2 H3 N)'
_chemical_formula_sum            'C36.60 H29.40 Cl2 Cu2 F5 N4.80 O2'
_chemical_formula_weight         861.43
_chemical_absolute_configuration ad

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'
F F 0.0171 0.0103 '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'

_cell_length_a                   9.1219(3)
_cell_length_b                   9.5962(3)
_cell_length_c                   11.4690(5)
_cell_angle_alpha                77.4552(14)
_cell_angle_beta                 66.6665(16)
_cell_angle_gamma                70.856(2)
_cell_volume                     866.44(6)
_cell_formula_units_Z            1
_cell_measurement_temperature    150(2)
_cell_measurement_reflns_used    59
_cell_measurement_theta_min      3.708
_cell_measurement_theta_max      21.631

_exptl_crystal_description       block
_exptl_crystal_colour            olive-green
_exptl_crystal_size_max          0.22
_exptl_crystal_size_mid          0.1
_exptl_crystal_size_min          0.1
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.651
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             435.6
_exptl_absorpt_coefficient_mu    1.451
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.66
_exptl_absorpt_correction_T_max  0.87
_exptl_absorpt_process_details   'SADABS (Sheldrick, 2004)'

_exptl_special_details           
;
Due to solvent loss from the crystal the acetonitrile was only partially
present, and the occupancy was refined to 80%. The structure is pseudo-
centrosymmetric and inversion twinned, with a twin ratio of 55.6 / 44.4.
The crystal was poor quality, with diffraction only observable to a resolution
of 0.84\%A. It was necessary to restrain all non-hydrogen atoms other than Cu
and F to approximate isotropic behaviour with a SHELX ISOR command.
;

_diffrn_ambient_temperature      150(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'rotating annode'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Nonius KappaCCD'
_diffrn_measurement_method       'Phi and omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         0
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            20015
_diffrn_reflns_av_R_equivalents  0.0652
_diffrn_reflns_av_sigmaI/netI    0.0713
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_theta_min         1.94
_diffrn_reflns_theta_max         25.00
_reflns_number_total             6029
_reflns_number_gt                4699
_reflns_threshold_expression     I>2\s(I)

_computing_data_collection       'Nonius Collect (Hooft, 1998)'
_computing_cell_refinement       'DIRAX (Duisenberg, 1992)'
_computing_data_reduction        'EvalCCD (Duisenberg et al., 2003)'
_computing_structure_solution    'DIRDIF (Beurskens et al., 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    'PLATON (Spek, 2003)'
_computing_publication_material  'PLATON (Spek, 2003)'

_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^)+(0.0716P)^2^+0.5573P] 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   0.452(19)
_refine_ls_number_reflns         6029
_refine_ls_number_parameters     485
_refine_ls_number_restraints     300
_refine_ls_R_factor_all          0.0759
_refine_ls_R_factor_gt           0.0508
_refine_ls_wR_factor_ref         0.1332
_refine_ls_wR_factor_gt          0.1212
_refine_ls_goodness_of_fit_ref   1.058
_refine_ls_restrained_S_all      1.075
_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 -0.00275(8) 0.48795(7) 0.05814(6) 0.0230(3) Uani 1 1 d . . .
Cu2 Cu 0.11272(8) 0.39088(8) 0.29439(7) 0.0210(3) Uani 1 1 d . . .
Cl1 Cl -0.1759(3) 0.6955(3) -0.0040(2) 0.0286(6) Uani 1 1 d . . .
Cl2 Cl 0.2889(3) 0.1853(3) 0.3531(2) 0.0286(7) Uani 1 1 d . . .
F2 F 0.0521(5) 0.0979(5) 0.2116(4) 0.0453(11) Uani 1 1 d U . .
F3 F 0.1714(6) -0.1367(5) 0.0776(5) 0.0520(12) Uani 1 1 d U . .
F4 F 0.4521(8) -0.1592(7) -0.1311(6) 0.0719(18) Uani 1 1 d U . .
F5 F 0.6134(8) 0.0559(7) -0.2054(6) 0.0605(18) Uani 1 1 d U . .
F6 F 0.4801(5) 0.3032(5) -0.0837(4) 0.0430(11) Uani 1 1 d U . .
O1 O 0.1805(8) 0.3417(7) 0.1213(6) 0.0253(17) Uani 1 1 d U . .
O10 O -0.0616(8) 0.5279(7) 0.2330(6) 0.0255(17) Uani 1 1 d U . .
N20 N 0.1207(10) 0.4350(9) -0.1237(8) 0.022(2) Uani 1 1 d U . .
N29 N -0.1203(10) 0.3149(8) 0.0540(8) 0.023(2) Uani 1 1 d U . .
N40 N -0.0134(9) 0.4512(9) 0.4757(8) 0.021(2) Uani 1 1 d U . .
N49 N 0.2310(9) 0.5625(8) 0.2969(8) 0.022(2) Uani 1 1 d U . .
C1 C 0.2616(13) 0.2143(12) 0.0717(11) 0.033(3) Uani 1 1 d U . .
C2 C 0.1901(9) 0.0920(8) 0.1073(7) 0.0346(17) Uani 1 1 d U . .
C3 C 0.2553(10) -0.0311(8) 0.0381(7) 0.0378(18) Uani 1 1 d U . .
C4 C 0.3914(10) -0.0444(8) -0.0650(8) 0.0397(19) Uani 1 1 d U . .
C5 C 0.4759(10) 0.0641(9) -0.1048(8) 0.0431(19) Uani 1 1 d U . .
C6 C 0.4050(9) 0.1929(8) -0.0374(7) 0.0338(17) Uani 1 1 d U . .
C10 C -0.1664(14) 0.6600(12) 0.2888(12) 0.043(3) Uani 1 1 d U . .
H10A H -0.0987 0.7195 0.2913 0.064 Uiso 1 1 calc R . .
H10B H -0.2378 0.6352 0.3759 0.064 Uiso 1 1 calc R . .
H10C H -0.2353 0.7167 0.2379 0.064 Uiso 1 1 calc R . .
C21 C 0.2376(12) 0.4973(11) -0.2110(10) 0.023(3) Uani 1 1 d U . .
C22 C 0.3192(14) 0.4454(13) -0.3313(11) 0.033(3) Uani 1 1 d U . .
H22 H 0.3971 0.4939 -0.3936 0.039 Uiso 1 1 calc R . .
C23 C 0.2943(12) 0.3294(11) -0.3654(10) 0.031(3) Uani 1 1 d U . .
H23 H 0.3537 0.2980 -0.4486 0.037 Uiso 1 1 calc R . .
C24 C 0.1340(13) 0.1411(12) -0.2890(10) 0.033(3) Uani 1 1 d U . .
H24 H 0.1932 0.0997 -0.3682 0.039 Uiso 1 1 calc R . .
C25 C 0.0191(12) 0.0803(11) -0.2064(9) 0.027(3) Uani 1 1 d U . .
H25 H -0.0036 0.0003 -0.2264 0.032 Uiso 1 1 calc R . .
C26 C -0.2048(13) 0.0807(12) 0.0140(10) 0.032(3) Uani 1 1 d U . .
H26 H -0.2292 -0.0024 0.0008 0.038 Uiso 1 1 calc R . .
C27 C -0.2942(13) 0.1435(11) 0.1242(10) 0.031(3) Uani 1 1 d U . .
H27 H -0.3859 0.1117 0.1864 0.037 Uiso 1 1 calc R . .
C28 C -0.2434(13) 0.2602(12) 0.1420(10) 0.031(3) Uani 1 1 d U . .
C30 C 0.1792(12) 0.2581(11) -0.2745(10) 0.027(3) Uani 1 1 d U . .
C31 C 0.0887(12) 0.3163(11) -0.1522(10) 0.024(3) Uani 1 1 d U . .
C32 C -0.0703(12) 0.1372(10) -0.0867(10) 0.025(3) Uani 1 1 d U . .
C33 C -0.0414(12) 0.2522(12) -0.0551(10) 0.026(3) Uani 1 1 d U . .
C34 C 0.2711(14) 0.6197(13) -0.1739(12) 0.044(3) Uani 1 1 d U . .
H34A H 0.2279 0.6171 -0.0806 0.066 Uiso 1 1 calc R . .
H34B H 0.2165 0.7150 -0.2105 0.066 Uiso 1 1 calc R . .
H34C H 0.3909 0.6077 -0.2060 0.066 Uiso 1 1 calc R . .
C35 C -0.3310(11) 0.3314(11) 0.2655(9) 0.029(3) Uani 1 1 d U . .
H35A H -0.3472 0.4389 0.2472 0.043 Uiso 1 1 calc R . .
H35B H -0.2637 0.2916 0.3200 0.043 Uiso 1 1 calc R . .
H35C H -0.4390 0.3100 0.3094 0.043 Uiso 1 1 calc R . .
C41 C -0.1227(13) 0.3880(11) 0.5626(11) 0.030(3) Uani 1 1 d U . .
C42 C -0.2156(13) 0.4377(12) 0.6867(10) 0.030(3) Uani 1 1 d U . .
H42 H -0.2939 0.3899 0.7493 0.036 Uiso 1 1 calc R . .
C43 C -0.1865(12) 0.5561(11) 0.7104(10) 0.032(3) Uani 1 1 d U . .
H43 H -0.2499 0.5962 0.7898 0.038 Uiso 1 1 calc R . .
C44 C -0.0361(12) 0.7493(11) 0.6513(10) 0.027(2) Uani 1 1 d U . .
H44 H -0.0966 0.7896 0.7310 0.033 Uiso 1 1 calc R . .
C45 C 0.0878(14) 0.8071(12) 0.5539(10) 0.034(3) Uani 1 1 d U . .
H45 H 0.1088 0.8915 0.5680 0.041 Uiso 1 1 calc R . .
C46 C 0.3096(13) 0.7939(11) 0.3459(10) 0.029(3) Uani 1 1 d U . .
H46 H 0.3401 0.8731 0.3594 0.035 Uiso 1 1 calc R . .
C47 C 0.3937(13) 0.7270(11) 0.2351(10) 0.031(3) Uani 1 1 d U . .
H47 H 0.4835 0.7612 0.1724 0.037 Uiso 1 1 calc R . .
C48 C 0.3539(11) 0.6119(10) 0.2106(9) 0.020(2) Uani 1 1 d U . .
C50 C -0.0653(13) 0.6203(11) 0.6205(10) 0.028(3) Uani 1 1 d U . .
C51 C 0.0169(12) 0.5631(11) 0.5048(9) 0.021(3) Uani 1 1 d U . .
C52 C 0.1433(12) 0.6222(10) 0.4123(9) 0.019(2) Uani 1 1 d U . .
C53 C 0.1843(12) 0.7459(11) 0.4342(10) 0.026(3) Uani 1 1 d U . .
C54 C -0.1512(11) 0.2549(10) 0.5316(9) 0.025(2) Uani 1 1 d U . .
H54A H -0.0481 0.2004 0.4708 0.037 Uiso 1 1 calc R . .
H54B H -0.2381 0.2889 0.4941 0.037 Uiso 1 1 calc R . .
H54C H -0.1856 0.1897 0.6101 0.037 Uiso 1 1 calc R . .
C55 C 0.4454(12) 0.5421(11) 0.0883(10) 0.032(3) Uani 1 1 d U . .
H55A H 0.4160 0.6108 0.0192 0.049 Uiso 1 1 calc R . .
H55B H 0.4152 0.4505 0.0964 0.049 Uiso 1 1 calc R . .
H55C H 0.5650 0.5192 0.0691 0.049 Uiso 1 1 calc R . .
N60 N 0.4898(13) 0.7913(12) 0.5619(11) 0.052(3) Uani 0.80 1 d PDU . .
C61 C 0.5693(15) 0.8725(12) 0.5293(11) 0.057(3) Uani 0.80 1 d PDU . .
C62 C 0.6525(17) 0.9888(14) 0.4823(13) 0.066(4) Uani 0.80 1 d PDU . .
H62A H 0.6949 0.9985 0.5455 0.099 Uiso 0.80 1 calc PR . .
H62B H 0.5742 1.0826 0.4670 0.099 Uiso 0.80 1 calc PR . .
H62C H 0.7450 0.9641 0.4022 0.099 Uiso 0.80 1 calc PR . .

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 0.0302(7) 0.0225(7) 0.0231(7) -0.0097(6) -0.0132(6) -0.0063(6)
Cu2 0.0257(6) 0.0232(7) 0.0203(7) -0.0078(5) -0.0110(5) -0.0074(6)
Cl1 0.0336(16) 0.0249(15) 0.0307(16) -0.0065(13) -0.0156(13) -0.0045(13)
Cl2 0.0348(16) 0.0241(15) 0.0321(16) -0.0050(13) -0.0171(13) -0.0064(13)
F2 0.046(2) 0.047(2) 0.049(2) -0.0014(19) -0.023(2) -0.014(2)
F3 0.061(3) 0.039(2) 0.072(3) -0.007(2) -0.034(2) -0.019(2)
F4 0.089(4) 0.068(3) 0.076(3) -0.034(3) -0.034(3) -0.020(3)
F5 0.059(3) 0.064(3) 0.047(3) -0.021(3) -0.010(3) -0.003(3)
F6 0.046(2) 0.044(2) 0.044(2) -0.0044(19) -0.0191(19) -0.014(2)
O1 0.027(3) 0.028(3) 0.026(3) -0.003(3) -0.016(3) -0.005(3)
O10 0.031(3) 0.026(3) 0.025(3) -0.014(2) -0.016(3) 0.000(3)
N20 0.027(3) 0.019(3) 0.023(4) -0.002(3) -0.018(3) 0.002(3)
N29 0.027(4) 0.028(4) 0.026(4) -0.009(3) -0.014(3) -0.011(3)
N40 0.023(3) 0.025(4) 0.023(4) -0.009(3) -0.010(3) -0.012(3)
N49 0.024(3) 0.019(3) 0.023(4) -0.009(3) -0.010(3) -0.002(3)
C1 0.035(4) 0.034(4) 0.027(4) -0.005(3) -0.018(3) 0.003(3)
C2 0.039(4) 0.035(3) 0.032(3) -0.004(3) -0.017(3) -0.007(3)
C3 0.043(4) 0.037(4) 0.044(4) -0.005(3) -0.027(3) -0.010(3)
C4 0.044(4) 0.031(3) 0.045(4) -0.012(3) -0.021(3) 0.001(3)
C5 0.042(4) 0.047(4) 0.037(4) -0.008(3) -0.015(3) -0.004(3)
C6 0.040(3) 0.034(3) 0.035(3) -0.005(3) -0.021(3) -0.008(3)
C10 0.050(5) 0.039(5) 0.032(4) -0.012(3) -0.017(4) 0.004(4)
C21 0.024(4) 0.025(4) 0.024(4) -0.002(3) -0.015(3) -0.002(3)
C22 0.027(4) 0.040(4) 0.029(4) 0.002(3) -0.010(3) -0.010(3)
C23 0.032(4) 0.042(4) 0.022(4) -0.003(3) -0.014(3) -0.008(3)
C24 0.038(4) 0.037(4) 0.028(4) -0.017(3) -0.017(3) 0.000(3)
C25 0.036(4) 0.024(4) 0.025(4) -0.017(3) -0.010(3) -0.007(3)
C26 0.043(5) 0.031(4) 0.037(4) -0.010(3) -0.022(3) -0.016(3)
C27 0.039(4) 0.034(4) 0.033(4) -0.001(3) -0.020(3) -0.019(3)
C28 0.035(4) 0.036(5) 0.032(4) -0.002(3) -0.025(4) -0.006(3)
C30 0.027(4) 0.034(4) 0.022(4) -0.009(3) -0.015(3) 0.001(3)
C31 0.032(4) 0.029(4) 0.020(4) -0.009(3) -0.021(3) -0.001(3)
C32 0.029(4) 0.021(4) 0.032(4) -0.004(3) -0.016(3) -0.008(3)
C33 0.023(4) 0.030(4) 0.030(4) -0.005(3) -0.018(3) -0.002(3)
C34 0.049(5) 0.045(5) 0.045(5) -0.003(4) -0.020(4) -0.018(4)
C35 0.028(4) 0.032(4) 0.023(4) -0.007(3) -0.004(3) -0.008(3)
C41 0.034(4) 0.029(4) 0.036(4) -0.004(3) -0.017(3) -0.014(3)
C42 0.030(4) 0.038(4) 0.024(4) -0.005(3) -0.013(3) -0.006(3)
C43 0.029(4) 0.034(4) 0.029(4) -0.011(3) -0.009(3) -0.001(3)
C44 0.034(4) 0.023(4) 0.026(4) -0.018(3) -0.011(3) 0.000(3)
C45 0.041(4) 0.031(4) 0.042(5) -0.011(3) -0.027(4) -0.004(3)
C46 0.038(4) 0.023(4) 0.031(4) -0.003(3) -0.013(3) -0.011(3)
C47 0.033(4) 0.031(4) 0.032(4) 0.000(3) -0.009(3) -0.018(3)
C48 0.022(4) 0.017(4) 0.022(4) -0.008(3) -0.006(3) -0.006(3)
C50 0.034(4) 0.029(4) 0.024(4) -0.006(3) -0.013(3) -0.008(3)
C51 0.022(4) 0.016(4) 0.026(4) -0.008(3) -0.008(3) -0.003(3)
C52 0.026(4) 0.013(4) 0.019(4) -0.005(3) -0.010(3) -0.004(3)
C53 0.034(4) 0.027(4) 0.028(4) -0.010(3) -0.021(3) -0.006(3)
C54 0.033(4) 0.030(4) 0.027(4) -0.002(3) -0.019(3) -0.019(3)
C55 0.041(5) 0.035(4) 0.033(4) -0.010(3) -0.016(3) -0.019(4)
N60 0.047(5) 0.055(5) 0.038(5) -0.004(4) -0.006(4) -0.006(4)
C61 0.064(5) 0.059(5) 0.044(5) -0.019(4) -0.023(4) 0.003(4)
C62 0.063(5) 0.084(6) 0.067(6) -0.005(4) -0.038(4) -0.022(4)

_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 O10 1.950(6) . ?
Cu1 N20 2.025(8) . ?
Cu1 O1 2.066(7) . ?
Cu1 N29 2.270(7) . ?
Cu1 Cl1 2.276(2) . ?
Cu2 O1 1.946(7) . ?
Cu2 O10 1.966(7) . ?
Cu2 N40 2.043(8) . ?
Cu2 N49 2.256(8) . ?
Cu2 Cl2 2.265(2) . ?
F2 C2 1.344(8) . ?
F3 C3 1.361(9) . ?
F4 C4 1.314(9) . ?
F5 C5 1.319(10) . ?
F6 C6 1.347(8) . ?
O1 C1 1.319(12) . ?
O10 C10 1.416(11) . ?
N20 C21 1.345(11) . ?
N20 C31 1.394(12) . ?
N29 C33 1.332(12) . ?
N29 C28 1.346(11) . ?
N40 C41 1.305(12) . ?
N40 C51 1.329(11) . ?
N49 C48 1.314(10) . ?
N49 C52 1.382(11) . ?
C1 C6 1.400(13) . ?
C1 C2 1.433(13) . ?
C2 C3 1.397(10) . ?
C3 C4 1.324(11) . ?
C4 C5 1.389(11) . ?
C5 C6 1.427(11) . ?
C10 H10A 0.9800 . ?
C10 H10B 0.9800 . ?
C10 H10C 0.9800 . ?
C21 C22 1.395(14) . ?
C21 C34 1.487(14) . ?
C22 C23 1.368(14) . ?
C22 H22 0.9500 . ?
C23 C30 1.397(13) . ?
C23 H23 0.9500 . ?
C24 C25 1.308(13) . ?
C24 C30 1.378(14) . ?
C24 H24 0.9500 . ?
C25 C32 1.413(12) . ?
C25 H25 0.9500 . ?
C26 C27 1.348(12) . ?
C26 C32 1.475(13) . ?
C26 H26 0.9500 . ?
C27 C28 1.423(13) . ?
C27 H27 0.9500 . ?
C28 C35 1.509(13) . ?
C30 C31 1.443(12) . ?
C31 C33 1.470(13) . ?
C32 C33 1.363(13) . ?
C34 H34A 0.9800 . ?
C34 H34B 0.9800 . ?
C34 H34C 0.9800 . ?
C35 H35A 0.9800 . ?
C35 H35B 0.9800 . ?
C35 H35C 0.9800 . ?
C41 C42 1.430(14) . ?
C41 C54 1.521(12) . ?
C42 C43 1.350(14) . ?
C42 H42 0.9500 . ?
C43 C50 1.390(13) . ?
C43 H43 0.9500 . ?
C44 C45 1.406(13) . ?
C44 C50 1.486(13) . ?
C44 H44 0.9500 . ?
C45 C53 1.434(13) . ?
C45 H45 0.9500 . ?
C46 C53 1.331(13) . ?
C46 C47 1.369(13) . ?
C46 H46 0.9500 . ?
C47 C48 1.382(13) . ?
C47 H47 0.9500 . ?
C48 C55 1.492(12) . ?
C50 C51 1.372(13) . ?
C51 C52 1.405(12) . ?
C52 C53 1.452(12) . ?
C54 H54A 0.9800 . ?
C54 H54B 0.9800 . ?
C54 H54C 0.9800 . ?
C55 H55A 0.9800 . ?
C55 H55B 0.9800 . ?
C55 H55C 0.9800 . ?
N60 C61 1.142(8) . ?
C61 C62 1.443(8) . ?
C62 H62A 0.9800 . ?
C62 H62B 0.9800 . ?
C62 H62C 0.9800 . ?

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
O10 Cu1 N20 164.6(3) . . ?
O10 Cu1 O1 74.2(2) . . ?
N20 Cu1 O1 92.9(3) . . ?
O10 Cu1 N29 110.7(3) . . ?
N20 Cu1 N29 78.4(3) . . ?
O1 Cu1 N29 96.1(3) . . ?
O10 Cu1 Cl1 98.6(2) . . ?
N20 Cu1 Cl1 91.8(2) . . ?
O1 Cu1 Cl1 164.32(19) . . ?
N29 Cu1 Cl1 99.5(2) . . ?
O1 Cu2 O10 76.6(3) . . ?
O1 Cu2 N40 166.4(3) . . ?
O10 Cu2 N40 92.2(3) . . ?
O1 Cu2 N49 110.7(3) . . ?
O10 Cu2 N49 96.8(3) . . ?
N40 Cu2 N49 77.7(3) . . ?
O1 Cu2 Cl2 94.9(2) . . ?
O10 Cu2 Cl2 163.97(18) . . ?
N40 Cu2 Cl2 94.1(2) . . ?
N49 Cu2 Cl2 98.9(2) . . ?
C1 O1 Cu2 130.5(7) . . ?
C1 O1 Cu1 119.6(7) . . ?
Cu2 O1 Cu1 102.8(3) . . ?
C10 O10 Cu1 126.7(7) . . ?
C10 O10 Cu2 123.0(7) . . ?
Cu1 O10 Cu2 106.4(3) . . ?
C21 N20 C31 120.0(9) . . ?
C21 N20 Cu1 124.4(7) . . ?
C31 N20 Cu1 115.3(7) . . ?
C33 N29 C28 116.5(8) . . ?
C33 N29 Cu1 110.9(6) . . ?
C28 N29 Cu1 132.3(7) . . ?
C41 N40 C51 118.7(9) . . ?
C41 N40 Cu2 123.9(7) . . ?
C51 N40 Cu2 117.4(7) . . ?
C48 N49 C52 121.0(7) . . ?
C48 N49 Cu2 131.8(6) . . ?
C52 N49 Cu2 107.2(5) . . ?
O1 C1 C6 124.8(10) . . ?
O1 C1 C2 121.9(9) . . ?
C6 C1 C2 111.9(9) . . ?
F2 C2 C3 118.9(7) . . ?
F2 C2 C1 117.9(7) . . ?
C3 C2 C1 123.2(8) . . ?
C4 C3 F3 120.3(7) . . ?
C4 C3 C2 121.9(7) . . ?
F3 C3 C2 117.8(7) . . ?
F4 C4 C3 122.1(8) . . ?
F4 C4 C5 118.0(8) . . ?
C3 C4 C5 119.8(7) . . ?
F5 C5 C4 122.6(8) . . ?
F5 C5 C6 119.2(8) . . ?
C4 C5 C6 118.1(7) . . ?
F6 C6 C1 117.6(7) . . ?
F6 C6 C5 117.5(7) . . ?
C1 C6 C5 124.9(8) . . ?
O10 C10 H10A 109.5 . . ?
O10 C10 H10B 109.5 . . ?
H10A C10 H10B 109.5 . . ?
O10 C10 H10C 109.5 . . ?
H10A C10 H10C 109.5 . . ?
H10B C10 H10C 109.5 . . ?
N20 C21 C22 118.7(9) . . ?
N20 C21 C34 117.7(9) . . ?
C22 C21 C34 123.6(10) . . ?
C23 C22 C21 124.3(10) . . ?
C23 C22 H22 117.9 . . ?
C21 C22 H22 117.9 . . ?
C22 C23 C30 118.2(10) . . ?
C22 C23 H23 120.9 . . ?
C30 C23 H23 120.9 . . ?
C25 C24 C30 127.6(10) . . ?
C25 C24 H24 116.2 . . ?
C30 C24 H24 116.2 . . ?
C24 C25 C32 118.0(9) . . ?
C24 C25 H25 121.0 . . ?
C32 C25 H25 121.0 . . ?
C27 C26 C32 121.9(9) . . ?
C27 C26 H26 119.1 . . ?
C32 C26 H26 119.1 . . ?
C26 C27 C28 116.2(10) . . ?
C26 C27 H27 121.9 . . ?
C28 C27 H27 121.9 . . ?
N29 C28 C27 124.2(10) . . ?
N29 C28 C35 116.0(9) . . ?
C27 C28 C35 119.7(9) . . ?
C24 C30 C23 127.7(10) . . ?
C24 C30 C31 114.6(9) . . ?
C23 C30 C31 117.6(9) . . ?
N20 C31 C30 121.1(9) . . ?
N20 C31 C33 118.5(9) . . ?
C30 C31 C33 120.4(8) . . ?
C33 C32 C25 122.5(9) . . ?
C33 C32 C26 114.0(10) . . ?
C25 C32 C26 123.5(9) . . ?
N29 C33 C32 127.0(9) . . ?
N29 C33 C31 116.1(8) . . ?
C32 C33 C31 116.9(10) . . ?
C21 C34 H34A 109.5 . . ?
C21 C34 H34B 109.5 . . ?
H34A C34 H34B 109.5 . . ?
C21 C34 H34C 109.5 . . ?
H34A C34 H34C 109.5 . . ?
H34B C34 H34C 109.5 . . ?
C28 C35 H35A 109.5 . . ?
C28 C35 H35B 109.5 . . ?
H35A C35 H35B 109.5 . . ?
C28 C35 H35C 109.5 . . ?
H35A C35 H35C 109.5 . . ?
H35B C35 H35C 109.5 . . ?
N40 C41 C42 122.6(9) . . ?
N40 C41 C54 118.8(9) . . ?
C42 C41 C54 118.6(9) . . ?
C43 C42 C41 116.7(10) . . ?
C43 C42 H42 121.7 . . ?
C41 C42 H42 121.7 . . ?
C42 C43 C50 121.2(10) . . ?
C42 C43 H43 119.4 . . ?
C50 C43 H43 119.4 . . ?
C45 C44 C50 115.0(9) . . ?
C45 C44 H44 122.5 . . ?
C50 C44 H44 122.5 . . ?
C44 C45 C53 123.7(10) . . ?
C44 C45 H45 118.2 . . ?
C53 C45 H45 118.2 . . ?
C53 C46 C47 118.7(10) . . ?
C53 C46 H46 120.7 . . ?
C47 C46 H46 120.7 . . ?
C46 C47 C48 122.9(9) . . ?
C46 C47 H47 118.6 . . ?
C48 C47 H47 118.6 . . ?
N49 C48 C47 119.3(9) . . ?
N49 C48 C55 118.6(8) . . ?
C47 C48 C55 122.1(9) . . ?
C51 C50 C43 117.1(9) . . ?
C51 C50 C44 123.5(9) . . ?
C43 C50 C44 119.3(10) . . ?
N40 C51 C50 123.5(9) . . ?
N40 C51 C52 117.4(9) . . ?
C50 C51 C52 119.0(8) . . ?
N49 C52 C51 119.7(8) . . ?
N49 C52 C53 118.6(8) . . ?
C51 C52 C53 121.6(9) . . ?
C46 C53 C45 123.6(10) . . ?
C46 C53 C52 119.4(10) . . ?
C45 C53 C52 117.0(9) . . ?
C41 C54 H54A 109.5 . . ?
C41 C54 H54B 109.5 . . ?
H54A C54 H54B 109.5 . . ?
C41 C54 H54C 109.5 . . ?
H54A C54 H54C 109.5 . . ?
H54B C54 H54C 109.5 . . ?
C48 C55 H55A 109.5 . . ?
C48 C55 H55B 109.5 . . ?
H55A C55 H55B 109.5 . . ?
C48 C55 H55C 109.5 . . ?
H55A C55 H55C 109.5 . . ?
H55B C55 H55C 109.5 . . ?
N60 C61 C62 172.3(14) . . ?
C61 C62 H62A 109.5 . . ?
C61 C62 H62B 109.5 . . ?
H62A C62 H62B 109.5 . . ?
C61 C62 H62C 109.5 . . ?
H62A C62 H62C 109.5 . . ?
H62B C62 H62C 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
O10 Cu2 O1 C1 -148.7(8) . . . . ?
N40 Cu2 O1 C1 -114.0(15) . . . . ?
N49 Cu2 O1 C1 119.0(8) . . . . ?
Cl2 Cu2 O1 C1 17.5(9) . . . . ?
O10 Cu2 O1 Cu1 0.5(3) . . . . ?
N40 Cu2 O1 Cu1 35.3(15) . . . . ?
N49 Cu2 O1 Cu1 -91.8(3) . . . . ?
Cl2 Cu2 O1 Cu1 166.8(2) . . . . ?
O10 Cu1 O1 C1 152.9(7) . . . . ?
N20 Cu1 O1 C1 -35.6(8) . . . . ?
N29 Cu1 O1 C1 43.0(8) . . . . ?
Cl1 Cu1 O1 C1 -143.0(7) . . . . ?
O10 Cu1 O1 Cu2 -0.5(3) . . . . ?
N20 Cu1 O1 Cu2 170.9(3) . . . . ?
N29 Cu1 O1 Cu2 -110.4(3) . . . . ?
Cl1 Cu1 O1 Cu2 63.6(8) . . . . ?
N20 Cu1 O10 C10 124.7(13) . . . . ?
O1 Cu1 O10 C10 158.6(8) . . . . ?
N29 Cu1 O10 C10 -110.7(8) . . . . ?
Cl1 Cu1 O10 C10 -7.1(8) . . . . ?
N20 Cu1 O10 Cu2 -33.4(13) . . . . ?
O1 Cu1 O10 Cu2 0.5(3) . . . . ?
N29 Cu1 O10 Cu2 91.1(3) . . . . ?
Cl1 Cu1 O10 Cu2 -165.2(2) . . . . ?
O1 Cu2 O10 C10 -159.7(7) . . . . ?
N40 Cu2 O10 C10 28.0(8) . . . . ?
N49 Cu2 O10 C10 -49.9(8) . . . . ?
Cl2 Cu2 O10 C10 141.2(7) . . . . ?
O1 Cu2 O10 Cu1 -0.6(4) . . . . ?
N40 Cu2 O10 Cu1 -172.9(3) . . . . ?
N49 Cu2 O10 Cu1 109.2(3) . . . . ?
Cl2 Cu2 O10 Cu1 -59.7(9) . . . . ?
O10 Cu1 N20 C21 -53.0(15) . . . . ?
O1 Cu1 N20 C21 -85.6(7) . . . . ?
N29 Cu1 N20 C21 178.8(7) . . . . ?
Cl1 Cu1 N20 C21 79.5(7) . . . . ?
O10 Cu1 N20 C31 121.0(12) . . . . ?
O1 Cu1 N20 C31 88.5(6) . . . . ?
N29 Cu1 N20 C31 -7.1(6) . . . . ?
Cl1 Cu1 N20 C31 -106.5(6) . . . . ?
O10 Cu1 N29 C33 -159.8(7) . . . . ?
N20 Cu1 N29 C33 7.3(6) . . . . ?
O1 Cu1 N29 C33 -84.4(7) . . . . ?
Cl1 Cu1 N29 C33 97.2(6) . . . . ?
O10 Cu1 N29 C28 15.4(9) . . . . ?
N20 Cu1 N29 C28 -177.5(9) . . . . ?
O1 Cu1 N29 C28 90.7(8) . . . . ?
Cl1 Cu1 N29 C28 -87.6(8) . . . . ?
O1 Cu2 N40 C41 54.8(18) . . . . ?
O10 Cu2 N40 C41 88.5(8) . . . . ?
N49 Cu2 N40 C41 -175.0(8) . . . . ?
Cl2 Cu2 N40 C41 -76.8(8) . . . . ?
O1 Cu2 N40 C51 -124.1(13) . . . . ?
O10 Cu2 N40 C51 -90.4(7) . . . . ?
N49 Cu2 N40 C51 6.2(7) . . . . ?
Cl2 Cu2 N40 C51 104.4(7) . . . . ?
O1 Cu2 N49 C48 -13.8(9) . . . . ?
O10 Cu2 N49 C48 -91.9(8) . . . . ?
N40 Cu2 N49 C48 177.3(9) . . . . ?
Cl2 Cu2 N49 C48 85.0(8) . . . . ?
O1 Cu2 N49 C52 163.2(6) . . . . ?
O10 Cu2 N49 C52 85.0(6) . . . . ?
N40 Cu2 N49 C52 -5.8(6) . . . . ?
Cl2 Cu2 N49 C52 -98.1(6) . . . . ?
Cu2 O1 C1 C6 -126.8(9) . . . . ?
Cu1 O1 C1 C6 88.2(11) . . . . ?
Cu2 O1 C1 C2 67.9(12) . . . . ?
Cu1 O1 C1 C2 -77.1(11) . . . . ?
O1 C1 C2 F2 -13.6(13) . . . . ?
C6 C1 C2 F2 179.4(7) . . . . ?
O1 C1 C2 C3 165.4(9) . . . . ?
C6 C1 C2 C3 -1.6(12) . . . . ?
F2 C2 C3 C4 -179.5(7) . . . . ?
C1 C2 C3 C4 1.5(12) . . . . ?
F2 C2 C3 F3 2.4(10) . . . . ?
C1 C2 C3 F3 -176.6(7) . . . . ?
F3 C3 C4 F4 -1.2(11) . . . . ?
C2 C3 C4 F4 -179.3(7) . . . . ?
F3 C3 C4 C5 179.8(7) . . . . ?
C2 C3 C4 C5 1.8(12) . . . . ?
F4 C4 C5 F5 0.0(12) . . . . ?
C3 C4 C5 F5 179.0(7) . . . . ?
F4 C4 C5 C6 176.5(7) . . . . ?
C3 C4 C5 C6 -4.6(11) . . . . ?
O1 C1 C6 F6 10.8(14) . . . . ?
C2 C1 C6 F6 177.3(7) . . . . ?
O1 C1 C6 C5 -168.0(9) . . . . ?
C2 C1 C6 C5 -1.4(12) . . . . ?
F5 C5 C6 F6 2.4(11) . . . . ?
C4 C5 C6 F6 -174.2(7) . . . . ?
F5 C5 C6 C1 -178.9(8) . . . . ?
C4 C5 C6 C1 4.5(12) . . . . ?
C31 N20 C21 C22 3.0(13) . . . . ?
Cu1 N20 C21 C22 176.8(7) . . . . ?
C31 N20 C21 C34 -177.7(8) . . . . ?
Cu1 N20 C21 C34 -3.9(12) . . . . ?
N20 C21 C22 C23 -3.4(15) . . . . ?
C34 C21 C22 C23 177.4(10) . . . . ?
C21 C22 C23 C30 0.4(15) . . . . ?
C30 C24 C25 C32 -0.9(17) . . . . ?
C32 C26 C27 C28 -4.6(14) . . . . ?
C33 N29 C28 C27 -1.1(14) . . . . ?
Cu1 N29 C28 C27 -176.0(7) . . . . ?
C33 N29 C28 C35 179.6(9) . . . . ?
Cu1 N29 C28 C35 4.7(13) . . . . ?
C26 C27 C28 N29 3.8(15) . . . . ?
C26 C27 C28 C35 -176.9(9) . . . . ?
C25 C24 C30 C23 -175.5(10) . . . . ?
C25 C24 C30 C31 1.1(16) . . . . ?
C22 C23 C30 C24 179.2(10) . . . . ?
C22 C23 C30 C31 2.7(14) . . . . ?
C21 N20 C31 C30 0.0(13) . . . . ?
Cu1 N20 C31 C30 -174.3(7) . . . . ?
C21 N20 C31 C33 -179.2(8) . . . . ?
Cu1 N20 C31 C33 6.4(10) . . . . ?
C24 C30 C31 N20 -179.9(9) . . . . ?
C23 C30 C31 N20 -3.0(13) . . . . ?
C24 C30 C31 C33 -0.6(13) . . . . ?
C23 C30 C31 C33 176.3(8) . . . . ?
C24 C25 C32 C33 0.2(15) . . . . ?
C24 C25 C32 C26 178.9(9) . . . . ?
C27 C26 C32 C33 2.8(14) . . . . ?
C27 C26 C32 C25 -175.9(10) . . . . ?
C28 N29 C33 C32 -1.0(15) . . . . ?
Cu1 N29 C33 C32 175.0(8) . . . . ?
C28 N29 C33 C31 177.9(8) . . . . ?
Cu1 N29 C33 C31 -6.2(10) . . . . ?
C25 C32 C33 N29 178.9(10) . . . . ?
C26 C32 C33 N29 0.2(15) . . . . ?
C25 C32 C33 C31 0.1(14) . . . . ?
C26 C32 C33 C31 -178.7(8) . . . . ?
N20 C31 C33 N29 0.4(13) . . . . ?
C30 C31 C33 N29 -178.8(9) . . . . ?
N20 C31 C33 C32 179.4(9) . . . . ?
C30 C31 C33 C32 0.1(13) . . . . ?
C51 N40 C41 C42 2.3(15) . . . . ?
Cu2 N40 C41 C42 -176.6(7) . . . . ?
C51 N40 C41 C54 -176.9(8) . . . . ?
Cu2 N40 C41 C54 4.3(13) . . . . ?
N40 C41 C42 C43 0.7(16) . . . . ?
C54 C41 C42 C43 179.9(9) . . . . ?
C41 C42 C43 C50 -3.5(15) . . . . ?
C50 C44 C45 C53 -1.8(14) . . . . ?
C53 C46 C47 C48 0.3(15) . . . . ?
C52 N49 C48 C47 -1.1(13) . . . . ?
Cu2 N49 C48 C47 175.5(7) . . . . ?
C52 N49 C48 C55 179.3(8) . . . . ?
Cu2 N49 C48 C55 -4.1(13) . . . . ?
C46 C47 C48 N49 -0.6(15) . . . . ?
C46 C47 C48 C55 179.0(9) . . . . ?
C42 C43 C50 C51 3.2(15) . . . . ?
C42 C43 C50 C44 -179.2(9) . . . . ?
C45 C44 C50 C51 -2.1(15) . . . . ?
C45 C44 C50 C43 -179.4(9) . . . . ?
C41 N40 C51 C50 -2.6(15) . . . . ?
Cu2 N40 C51 C50 176.3(8) . . . . ?
C41 N40 C51 C52 175.7(9) . . . . ?
Cu2 N40 C51 C52 -5.4(11) . . . . ?
C43 C50 C51 N40 -0.1(15) . . . . ?
C44 C50 C51 N40 -177.5(9) . . . . ?
C43 C50 C51 C52 -178.4(9) . . . . ?
C44 C50 C51 C52 4.2(15) . . . . ?
C48 N49 C52 C51 -177.5(9) . . . . ?
Cu2 N49 C52 C51 5.2(10) . . . . ?
C48 N49 C52 C53 2.9(13) . . . . ?
Cu2 N49 C52 C53 -174.4(7) . . . . ?
N40 C51 C52 N49 -0.5(13) . . . . ?
C50 C51 C52 N49 177.9(9) . . . . ?
N40 C51 C52 C53 179.1(9) . . . . ?
C50 C51 C52 C53 -2.5(14) . . . . ?
C47 C46 C53 C45 179.8(9) . . . . ?
C47 C46 C53 C52 1.6(14) . . . . ?
C44 C45 C53 C46 -174.9(10) . . . . ?
C44 C45 C53 C52 3.3(14) . . . . ?
N49 C52 C53 C46 -3.2(14) . . . . ?
C51 C52 C53 C46 177.2(9) . . . . ?
N49 C52 C53 C45 178.5(8) . . . . ?
C51 C52 C53 C45 -1.1(14) . . . . ?

_diffrn_measured_fraction_theta_max 1.000
_diffrn_reflns_theta_full        25.00
_diffrn_measured_fraction_theta_full 1.000
_refine_diff_density_max         0.832
_refine_diff_density_min         -0.641
_refine_diff_density_rms         0.111

data_2
_database_code_depnum_ccdc_archive 'CCDC 272664'

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C21 H19 Cl3 Cu2 N4 O'
_chemical_formula_sum            'C21 H19 Cl3 Cu2 N4 O'
_chemical_formula_weight         576.83

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           monoclinic
_symmetry_space_group_name_H-M   'C 2/c'
_symmetry_space_group_name_Hall  '-C 2yc'

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

_cell_length_a                   16.4463(10)
_cell_length_b                   7.7606(10)
_cell_length_c                   18.5145(9)
_cell_angle_alpha                90.00
_cell_angle_beta                 114.620(3)
_cell_angle_gamma                90.00
_cell_volume                     2148.2(3)
_cell_formula_units_Z            4
_cell_measurement_temperature    150(2)
_cell_measurement_reflns_used    27
_cell_measurement_theta_min      6.271
_cell_measurement_theta_max      18.872

_exptl_crystal_description       block
_exptl_crystal_colour            'dark green-blue'
_exptl_crystal_size_max          0.18
_exptl_crystal_size_mid          0.06
_exptl_crystal_size_min          0.03
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.784
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1160
_exptl_absorpt_coefficient_mu    2.376
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.61
_exptl_absorpt_correction_T_max  0.93
_exptl_absorpt_process_details   'SADABS (Sheldrick, 2004)'

_exptl_special_details           
;
?
;

_diffrn_ambient_temperature      150(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'rotating anode'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Nonius KappaCCD'
_diffrn_measurement_method       'Omega and phi scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            28223
_diffrn_reflns_av_R_equivalents  0.0623
_diffrn_reflns_av_sigmaI/netI    0.0312
_diffrn_reflns_limit_h_min       -21
_diffrn_reflns_limit_h_max       21
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_l_min       -23
_diffrn_reflns_limit_l_max       23
_diffrn_reflns_theta_min         2.42
_diffrn_reflns_theta_max         27.44
_reflns_number_total             2462
_reflns_number_gt                1965
_reflns_threshold_expression     I>2\s(I)

_computing_data_collection       'Nonius Collect (Hooft, 1998)'
_computing_cell_refinement       'DIRAX (Duisenberg, 1992)'
_computing_data_reduction        'EvalCCD (Duisenberg et al., 2003)'
_computing_structure_solution    'SHELXS-86 (Sheldrick, 1986)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    'PLATON (Spek, 2003)'
_computing_publication_material  'PLATON (Spek, 2003)'

_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^)+(0.0417P)^2^+3.4028P] 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         2462
_refine_ls_number_parameters     142
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0495
_refine_ls_R_factor_gt           0.0328
_refine_ls_wR_factor_ref         0.0818
_refine_ls_wR_factor_gt          0.0757
_refine_ls_goodness_of_fit_ref   1.042
_refine_ls_restrained_S_all      1.042
_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 0.06968(2) 0.33250(4) 0.344141(18) 0.02199(11) Uani 1 1 d . . .
Cl2 Cl -0.01076(4) 0.22851(10) 0.41030(4) 0.03000(18) Uani 1 1 d . . .
Cl3 Cl 0.0000 0.58417(12) 0.2500 0.0265(2) Uani 1 2 d S . .
O4 O 0.0000 0.2061(3) 0.2500 0.0231(6) Uani 1 2 d S . .
N6 N 0.18783(14) 0.2968(3) 0.33347(13) 0.0212(5) Uani 1 1 d . . .
N17 N 0.15388(14) 0.4608(3) 0.44031(13) 0.0234(5) Uani 1 1 d . . .
C5 C 0.0000 0.0258(5) 0.2500 0.0317(9) Uani 1 2 d S . .
H5A H -0.0588 -0.0163 0.2437 0.038 Uiso 0.50 1 d PR . .
H5B H 0.0459 -0.0163 0.3004 0.038 Uiso 0.50 1 d PR . .
H5C H 0.0129 -0.0163 0.2059 0.038 Uiso 0.50 1 d PR . .
C7 C 0.19795(18) 0.2153(4) 0.27417(15) 0.0247(6) Uani 1 1 d . . .
H7 H 0.1466 0.1713 0.2313 0.030 Uiso 1 1 calc R . .
C8 C 0.28130(18) 0.1931(4) 0.27330(16) 0.0267(6) Uani 1 1 d . . .
H8 H 0.2869 0.1330 0.2309 0.032 Uiso 1 1 calc R . .
C9 C 0.35616(18) 0.2596(4) 0.33502(16) 0.0281(6) Uani 1 1 d . . .
H9 H 0.4138 0.2449 0.3357 0.034 Uiso 1 1 calc R . .
C10 C 0.34590(18) 0.3475(4) 0.39560(16) 0.0254(6) Uani 1 1 d . . .
H10 H 0.3962 0.3967 0.4379 0.030 Uiso 1 1 calc R . .
C11 C 0.26081(17) 0.3628(3) 0.39367(15) 0.0202(5) Uani 1 1 d . . .
C12 C 0.24168(17) 0.4508(3) 0.45563(15) 0.0213(5) Uani 1 1 d . . .
C13 C 0.30728(18) 0.5194(4) 0.52406(15) 0.0259(6) Uani 1 1 d . . .
H13 H 0.3686 0.5110 0.5338 0.031 Uiso 1 1 calc R . .
C14 C 0.2821(2) 0.6005(4) 0.57829(16) 0.0295(6) Uani 1 1 d . . .
H14 H 0.3260 0.6482 0.6257 0.035 Uiso 1 1 calc R . .
C15 C 0.1928(2) 0.6112(4) 0.56267(16) 0.0292(6) Uani 1 1 d . . .
H15 H 0.1743 0.6666 0.5990 0.035 Uiso 1 1 calc R . .
C16 C 0.13068(19) 0.5400(4) 0.49323(17) 0.0289(6) Uani 1 1 d . . .
H16 H 0.0691 0.5476 0.4826 0.035 Uiso 1 1 calc 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 0.02046(17) 0.02594(19) 0.02458(19) -0.00163(14) 0.01435(14) -0.00143(13)
Cl2 0.0225(3) 0.0459(4) 0.0256(4) 0.0018(3) 0.0139(3) -0.0043(3)
Cl3 0.0316(5) 0.0222(5) 0.0319(5) 0.000 0.0194(4) 0.000
O4 0.0227(13) 0.0229(14) 0.0241(14) 0.000 0.0100(11) 0.000
N6 0.0217(11) 0.0245(12) 0.0197(11) 0.0023(9) 0.0109(9) 0.0012(9)
N17 0.0232(11) 0.0262(12) 0.0262(12) 0.0007(10) 0.0158(10) -0.0016(9)
C5 0.032(2) 0.026(2) 0.039(2) 0.000 0.0156(19) 0.000
C7 0.0250(13) 0.0311(15) 0.0204(13) 0.0003(11) 0.0118(11) 0.0009(11)
C8 0.0299(14) 0.0327(16) 0.0248(14) 0.0005(11) 0.0186(12) 0.0016(12)
C9 0.0227(14) 0.0364(16) 0.0330(16) 0.0041(13) 0.0192(12) 0.0037(12)
C10 0.0207(13) 0.0350(16) 0.0223(13) 0.0021(12) 0.0107(11) -0.0013(12)
C11 0.0225(13) 0.0202(13) 0.0207(13) 0.0048(10) 0.0116(11) 0.0019(10)
C12 0.0248(13) 0.0201(13) 0.0229(13) 0.0052(10) 0.0140(11) 0.0017(10)
C13 0.0242(13) 0.0279(15) 0.0250(14) 0.0016(11) 0.0098(12) 0.0031(11)
C14 0.0362(16) 0.0293(15) 0.0193(13) 0.0015(12) 0.0080(12) 0.0024(13)
C15 0.0390(16) 0.0286(15) 0.0260(14) 0.0000(12) 0.0195(13) 0.0017(13)
C16 0.0303(15) 0.0296(15) 0.0355(16) -0.0022(12) 0.0223(13) 0.0000(12)

_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 O4 1.9105(13) . ?
Cu1 N17 2.006(2) . ?
Cu1 N6 2.052(2) . ?
Cu1 Cl2 2.2917(7) . ?
Cu1 Cl3 2.5498(8) . ?
O4 C5 1.399(5) . ?
N6 C7 1.336(3) . ?
N6 C11 1.353(3) . ?
N17 C16 1.340(3) . ?
N17 C12 1.353(3) . ?
C5 H5A 0.9800 . ?
C5 H5B 0.9800 . ?
C5 H5C 0.9799 . ?
C7 C8 1.388(4) . ?
C7 H7 0.9500 . ?
C8 C9 1.384(4) . ?
C8 H8 0.9500 . ?
C9 C10 1.382(4) . ?
C9 H9 0.9500 . ?
C10 C11 1.390(4) . ?
C10 H10 0.9500 . ?
C11 C12 1.477(4) . ?
C12 C13 1.383(4) . ?
C13 C14 1.387(4) . ?
C13 H13 0.9500 . ?
C14 C15 1.375(4) . ?
C14 H14 0.9500 . ?
C15 C16 1.381(4) . ?
C15 H15 0.9500 . ?
C16 H16 0.9500 . ?

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
O4 Cu1 N17 174.00(6) . . ?
O4 Cu1 N6 94.30(6) . . ?
N17 Cu1 N6 79.70(9) . . ?
O4 Cu1 Cl2 92.66(4) . . ?
N17 Cu1 Cl2 92.24(6) . . ?
N6 Cu1 Cl2 141.68(6) . . ?
O4 Cu1 Cl3 80.90(7) . . ?
N17 Cu1 Cl3 100.02(7) . . ?
N6 Cu1 Cl3 102.20(6) . . ?
Cl2 Cu1 Cl3 116.10(2) . . ?
Cu1 Cl3 Cu1 80.01(3) 2 . ?
C5 O4 Cu1 120.91(7) . 2 ?
C5 O4 Cu1 120.91(7) . . ?
Cu1 O4 Cu1 118.19(13) 2 . ?
C7 N6 C11 119.0(2) . . ?
C7 N6 Cu1 126.16(18) . . ?
C11 N6 Cu1 114.86(17) . . ?
C16 N17 C12 118.5(2) . . ?
C16 N17 Cu1 125.12(18) . . ?
C12 N17 Cu1 116.07(18) . . ?
O4 C5 H5A 109.5 . . ?
O4 C5 H5B 109.5 . . ?
H5A C5 H5B 109.5 . . ?
O4 C5 H5C 109.5 . . ?
H5A C5 H5C 109.5 . . ?
H5B C5 H5C 109.5 . . ?
N6 C7 C8 122.0(3) . . ?
N6 C7 H7 119.0 . . ?
C8 C7 H7 119.0 . . ?
C9 C8 C7 119.1(3) . . ?
C9 C8 H8 120.4 . . ?
C7 C8 H8 120.4 . . ?
C10 C9 C8 119.1(2) . . ?
C10 C9 H9 120.4 . . ?
C8 C9 H9 120.4 . . ?
C9 C10 C11 118.9(2) . . ?
C9 C10 H10 120.5 . . ?
C11 C10 H10 120.5 . . ?
N6 C11 C10 121.8(2) . . ?
N6 C11 C12 114.3(2) . . ?
C10 C11 C12 123.9(2) . . ?
N17 C12 C13 121.8(2) . . ?
N17 C12 C11 114.7(2) . . ?
C13 C12 C11 123.5(2) . . ?
C12 C13 C14 118.9(2) . . ?
C12 C13 H13 120.5 . . ?
C14 C13 H13 120.5 . . ?
C15 C14 C13 119.3(3) . . ?
C15 C14 H14 120.3 . . ?
C13 C14 H14 120.3 . . ?
C14 C15 C16 118.9(3) . . ?
C14 C15 H15 120.6 . . ?
C16 C15 H15 120.6 . . ?
N17 C16 C15 122.6(3) . . ?
N17 C16 H16 118.7 . . ?
C15 C16 H16 118.7 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
O4 Cu1 Cl3 Cu1 0.0 . . . 2 ?
N17 Cu1 Cl3 Cu1 173.99(6) . . . 2 ?
N6 Cu1 Cl3 Cu1 92.47(6) . . . 2 ?
Cl2 Cu1 Cl3 Cu1 -88.50(3) . . . 2 ?
N6 Cu1 O4 C5 78.31(6) . . . . ?
Cl2 Cu1 O4 C5 -63.98(2) . . . . ?
Cl3 Cu1 O4 C5 180.0 . . . . ?
N6 Cu1 O4 Cu1 -101.69(6) . . . 2 ?
Cl2 Cu1 O4 Cu1 116.02(2) . . . 2 ?
Cl3 Cu1 O4 Cu1 0.0 . . . 2 ?
O4 Cu1 N6 C7 2.5(2) . . . . ?
N17 Cu1 N6 C7 -177.2(2) . . . . ?
Cl2 Cu1 N6 C7 102.3(2) . . . . ?
Cl3 Cu1 N6 C7 -79.1(2) . . . . ?
O4 Cu1 N6 C11 -176.93(18) . . . . ?
N17 Cu1 N6 C11 3.33(17) . . . . ?
Cl2 Cu1 N6 C11 -77.1(2) . . . . ?
Cl3 Cu1 N6 C11 101.47(17) . . . . ?
N6 Cu1 N17 C16 -179.0(2) . . . . ?
Cl2 Cu1 N17 C16 -36.7(2) . . . . ?
Cl3 Cu1 N17 C16 80.3(2) . . . . ?
N6 Cu1 N17 C12 -5.49(18) . . . . ?
Cl2 Cu1 N17 C12 136.78(18) . . . . ?
Cl3 Cu1 N17 C12 -106.22(18) . . . . ?
C11 N6 C7 C8 1.4(4) . . . . ?
Cu1 N6 C7 C8 -178.03(19) . . . . ?
N6 C7 C8 C9 -1.0(4) . . . . ?
C7 C8 C9 C10 -0.5(4) . . . . ?
C8 C9 C10 C11 1.6(4) . . . . ?
C7 N6 C11 C10 -0.2(4) . . . . ?
Cu1 N6 C11 C10 179.25(19) . . . . ?
C7 N6 C11 C12 179.7(2) . . . . ?
Cu1 N6 C11 C12 -0.8(3) . . . . ?
C9 C10 C11 N6 -1.3(4) . . . . ?
C9 C10 C11 C12 178.9(2) . . . . ?
C16 N17 C12 C13 0.2(4) . . . . ?
Cu1 N17 C12 C13 -173.7(2) . . . . ?
C16 N17 C12 C11 -179.4(2) . . . . ?
Cu1 N17 C12 C11 6.6(3) . . . . ?
N6 C11 C12 N17 -3.7(3) . . . . ?
C10 C11 C12 N17 176.2(2) . . . . ?
N6 C11 C12 C13 176.6(2) . . . . ?
C10 C11 C12 C13 -3.5(4) . . . . ?
N17 C12 C13 C14 0.0(4) . . . . ?
C11 C12 C13 C14 179.6(2) . . . . ?
C12 C13 C14 C15 -0.2(4) . . . . ?
C13 C14 C15 C16 0.2(4) . . . . ?
C12 N17 C16 C15 -0.2(4) . . . . ?
Cu1 N17 C16 C15 173.1(2) . . . . ?
C14 C15 C16 N17 0.0(4) . . . . ?

_diffrn_measured_fraction_theta_max 1.000
_diffrn_reflns_theta_full        27.44
_diffrn_measured_fraction_theta_full 1.000
_refine_diff_density_max         0.600
_refine_diff_density_min         -0.361
_refine_diff_density_rms         0.087