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


# Attachment '- cif data_song_ICpaper.cif' 

#========================================================================================================================================
#   CIF for compounds 1, 2, and 3
#========================================================================================================================================
#====================================================================

data_global
_journal_name_full               CrystEngComm
_journal_coden_cambridge         1350
#TrackingRef '- cif data_song_ICpaper.cif'

# 1. SUBMISSION DETAILS

_publ_contact_author_name        'Y.-F. Song'
_publ_contact_author_address     
; State Key Laboratory of Chemical Resource Engineering
Beijing University of Chemical Technology
100029, Beijing,
P. R. China.
;
_publ_contact_author_email       songyufei@hotmail.com

#=============================================================================

# 3. TITLE AND AUTHOR LIST

_publ_section_title              
;
Tripodal bis(imidazole)-based ligands and their anion-dependent
chelation to Copper(II)
;

loop_
_publ_author_name
_publ_author_address

'Yu-Fei Song'
; State Key Laboratory of Chemical Resource Engineering
Beijing University of Chemical Technology
100029, Beijing,
P. R. China.
;
'Wei Chen'
; State Key Laboratory of Chemical Resource Engineering
Beijing University of Chemical Technology
100029, Beijing,
P. R. China.
;
'Jinfeng Chu'
; State Key Laboratory of Chemical Resource Engineering
Beijing University of Chemical Technology
100029, Beijing,
P. R. China.
;
'Dui Ma'
; State Key Laboratory of Chemical Resource Engineering
Beijing University of Chemical Technology
100029, Beijing,
P. R. China.
;
'Ilpo Mutikainen'
; Laboratory of Inorganic Chemistry, Department of Chemistry
P. O. Box 55, University of Helsinki, FIN-00014 Helsinki
Finland.
;
'Urho Turpeinen'
; Laboratory of Inorganic Chemistry, Department of Chemistry
P. O. Box 55, University of Helsinki, FIN-00014 Helsinki
Finland.
;
'Jan Reedijk'
; Leiden Institute of Chemistry, Gorlaeus Laboratories
Leiden University, P. O. Box 9502, 2300 RA Leiden
The Netherlands
;
#=============================================================================

# 4. TEXT

_publ_section_abstract           
;

;
_publ_section_comment            
;

;
_publ_section_experimental       
;
A crystal was selected for
the X--ray measurements and mounted to the glass fiber using the oil drop
method (Kottke & Stalke, 1993) and data were collected at 173 K.
The intensity data were corrected for Lorentz and polarization effects and for
absorption.
All nonhydrogen atoms were refined anisotropically. The H atoms of the
water molecules were determined from the difference map and their
coordinates were refined and temperature factors were riding with
the carrier atom. The other H atoms were introduced in calculated positions
and refined with fixed geometry with respect to their carrier atoms.

;
_publ_section_references         
;

Altomare, A., Burla, M.C., Camalli, M., Cascarano, G., Giacovazzo, C.,
Guagliardi, A., Moliterni, A.G.G., Polidori, G. & Spagna, R. (1999).
J. Appl. Cryst 32, 115-119.

Nonius (2002). COLLECT. Nonius BV, Delft, The Netherlands.

Kottke, T. and Stalke, D. (1993). J. Appl. Crystallogr. 26, 615--619.

Sheldrick, G.M. (1990). SHELXTL. University of G\"ottingen, Germany.

Sheldrick, G.M. (1996). SADABS. University of G\"ottingen, Germany.

Sheldrick, G.M. (1997). SHELX97. University of G\"ottingen, Germany.

;

_publ_section_figure_captions    
;
;
_publ_section_acknowledgements   
;

;

#===================================================================

data_1
_database_code_depnum_ccdc_archive 'CCDC 826231'
#TrackingRef '- cif data_song_ICpaper.cif'

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C26 H52 Cu2 F12 N12 O12 Si2'
_chemical_formula_weight         1136.06

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
Cu Cu 0.3201 1.2651 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Si Si 0.0817 0.0704 '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'
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'
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   C2/c

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

_cell_length_a                   26.823(4)
_cell_length_b                   8.765(2)
_cell_length_c                   20.686
_cell_angle_alpha                90.000(3)
_cell_angle_beta                 115.94(2)
_cell_angle_gamma                90.00
_cell_volume                     4373.4(12)
_cell_formula_units_Z            4
_cell_measurement_temperature    173(2)
_cell_measurement_reflns_used    13018
_cell_measurement_theta_min      3.05
_cell_measurement_theta_max      27.50

_exptl_crystal_description       plate
_exptl_crystal_colour            blue
_exptl_crystal_size_max          0.20
_exptl_crystal_size_mid          0.17
_exptl_crystal_size_min          0.11
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.725
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             2328
_exptl_absorpt_coefficient_mu    1.148
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.8029
_exptl_absorpt_correction_T_max  0.8841
_exptl_absorpt_process_details   'SADABS (Sheldrick, 1996)'

_exptl_special_details           
;
?
;

_diffrn_ambient_temperature      173(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  KappaCCD
_diffrn_measurement_method       \f-scan
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            13018
_diffrn_reflns_av_R_equivalents  0.0585
_diffrn_reflns_av_sigmaI/netI    0.0787
_diffrn_reflns_limit_h_min       -31
_diffrn_reflns_limit_h_max       26
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_limit_l_max       24
_diffrn_reflns_theta_min         3.05
_diffrn_reflns_theta_max         25.50
_reflns_number_total             3997
_reflns_number_gt                2779
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'COLLECT (Nonius, 2002)'
_computing_cell_refinement       'COLLECT (Nonius, 2002)'
_computing_data_reduction        'COLLECT (Nonius, 2002)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 1997)'
_computing_molecular_graphics    'SHELXTL (Sheldrick, 1990)'
_computing_publication_material  'SHELXTL (Sheldrick, 1990)'

_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^)+(0.0368P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         3997
_refine_ls_number_parameters     338
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0746
_refine_ls_R_factor_gt           0.0402
_refine_ls_wR_factor_ref         0.0828
_refine_ls_wR_factor_gt          0.0737
_refine_ls_goodness_of_fit_ref   0.957
_refine_ls_restrained_S_all      0.957
_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 0.034640(15) 0.91257(4) 0.08780(2) 0.01239(12) Uani 1 1 d . . .
N11 N 0.09560(10) 1.0537(3) 0.14904(13) 0.0128(6) Uani 1 1 d . . .
C12 C 0.14181(13) 1.0470(3) 0.13806(16) 0.0143(8) Uani 1 1 d . . .
C13 C 0.18931(13) 1.1263(3) 0.18223(18) 0.0200(8) Uani 1 1 d . . .
H13A H 0.2216 1.1202 0.1743 0.024 Uiso 1 1 calc R . .
C14 C 0.18944(15) 1.2144(3) 0.23795(18) 0.0248(9) Uani 1 1 d . . .
H14A H 0.2217 1.2694 0.2685 0.030 Uiso 1 1 calc R . .
C15 C 0.14254(14) 1.2213(4) 0.24850(18) 0.0229(9) Uani 1 1 d . . .
H15A H 0.1418 1.2819 0.2862 0.027 Uiso 1 1 calc R . .
C16 C 0.09603(13) 1.1390(3) 0.20363(16) 0.0167(8) Uani 1 1 d . . .
H16A H 0.0637 1.1427 0.2115 0.020 Uiso 1 1 calc R . .
C17 C 0.13704(13) 0.9580(3) 0.07358(17) 0.0165(8) Uani 1 1 d . . .
H17A H 0.1278 1.0274 0.0321 0.020 Uiso 1 1 calc R . .
H17B H 0.1727 0.9074 0.0840 0.020 Uiso 1 1 calc R . .
N18 N 0.09281(10) 0.8420(3) 0.05634(13) 0.0116(6) Uani 1 1 d . . .
H18A H 0.1101 0.7593 0.0858 0.014 Uiso 1 1 calc R . .
C19 C 0.06709(13) 0.7781(3) -0.01913(16) 0.0129(7) Uani 1 1 d . . .
H19A H 0.0895 0.6883 -0.0209 0.016 Uiso 1 1 calc R . .
N21 N -0.01183(10) 0.7690(3) 0.01108(14) 0.0136(6) Uani 1 1 d . . .
C22 C 0.01121(13) 0.7235(3) -0.03070(16) 0.0133(8) Uani 1 1 d . . .
N23 N -0.02196(11) 0.6241(3) -0.08069(14) 0.0173(7) Uani 1 1 d . . .
H23A H -0.0149 0.5798 -0.1140 0.021 Uiso 1 1 calc R . .
C24 C -0.06870(13) 0.6042(3) -0.07031(17) 0.0176(8) Uani 1 1 d . . .
H24A H -0.0995 0.5407 -0.0976 0.021 Uiso 1 1 calc R . .
C25 C -0.06245(13) 0.6928(3) -0.01358(17) 0.0167(8) Uani 1 1 d . . .
H25A H -0.0883 0.7015 0.0062 0.020 Uiso 1 1 calc R . .
N33 N 0.10461(10) 0.8984(3) -0.09732(13) 0.0161(6) Uani 1 1 d . . .
H33A H 0.1328 0.8354 -0.0850 0.019 Uiso 1 1 calc R . .
C32 C 0.06511(12) 0.8924(3) -0.07429(16) 0.0123(7) Uani 1 1 d . . .
N31 N 0.02808(10) 1.0049(3) -0.10463(13) 0.0139(6) Uani 1 1 d . . .
C35 C 0.04670(13) 1.0847(3) -0.14798(16) 0.0160(7) Uani 1 1 d . . .
H35A H 0.0292 1.1714 -0.1764 0.019 Uiso 1 1 calc R . .
C34 C 0.09351(14) 1.0192(3) -0.14318(16) 0.0184(8) Uani 1 1 d . . .
H34A H 0.1149 1.0510 -0.1672 0.022 Uiso 1 1 calc R . .
O1 O 0.06688(11) 0.7470(3) 0.18073(14) 0.0256(7) Uani 1 1 d . . .
H1A H 0.0552(17) 0.693(4) 0.193(2) 0.038 Uiso 1 1 d . . .
H1B H 0.1002(15) 0.752(4) 0.2074(19) 0.038 Uiso 1 1 d . . .
O2 O 0.15126(11) 1.4221(3) -0.10986(15) 0.0332(7) Uani 1 1 d . . .
H21 H 0.1230(16) 1.459(5) -0.123(2) 0.050 Uiso 1 1 d . . .
H22 H 0.1722(17) 1.484(4) -0.092(2) 0.050 Uiso 1 1 d . . .
O3 O 0.25543(11) 1.0652(3) -0.12606(14) 0.0283(7) Uani 1 1 d . . .
H31 H 0.2473(15) 0.987(4) -0.109(2) 0.043 Uiso 1 1 d . . .
H32 H 0.2727(15) 1.117(4) -0.090(2) 0.043 Uiso 1 1 d . . .
O4 O 0.32878(11) 0.8711(3) -0.15626(13) 0.0265(7) Uani 1 1 d . . .
H41 H 0.3070(16) 0.930(4) -0.154(2) 0.040 Uiso 1 1 d . . .
H42 H 0.3222(16) 0.864(4) -0.196(2) 0.040 Uiso 1 1 d . . .
O5 O 0.17522(11) 1.2737(3) -0.21178(15) 0.0300(7) Uani 1 1 d . . .
H5A H 0.1991(16) 1.208(4) -0.183(2) 0.045 Uiso 1 1 d . . .
H5B H 0.1709(17) 1.320(4) -0.182(2) 0.045(15) Uiso 1 1 d . . .
O6 O 0.19097(12) 1.2260(3) 0.01321(15) 0.0331(7) Uani 1 1 d . . .
H61 H 0.2019(17) 1.144(4) 0.012(2) 0.050 Uiso 1 1 d . . .
H62 H 0.1773(16) 1.267(4) -0.027(2) 0.050 Uiso 1 1 d . . .
Si1 Si 0.0000 0.44170(13) 0.2500 0.0159(3) Uani 1 2 d S . .
F11 F 0.04522(8) 0.4451(2) 0.33926(10) 0.0314(5) Uani 1 1 d . . .
F12 F 0.05283(8) 0.4478(2) 0.22745(10) 0.0286(5) Uani 1 1 d . . .
F13 F 0.0000 0.6348(3) 0.2500 0.0315(8) Uani 1 2 d S . .
F14 F 0.0000 0.2535(3) 0.2500 0.0329(8) Uani 1 2 d S . .
Si2 Si 0.2500 0.7500 0.0000 0.0152(3) Uani 1 2 d S . .
F21 F 0.24418(8) 0.92565(19) 0.02940(11) 0.0349(6) Uani 1 1 d . . .
F22 F 0.18905(7) 0.69797(19) -0.00218(10) 0.0266(5) Uani 1 1 d . . .
F23 F 0.28477(8) 0.6881(2) 0.08575(10) 0.0344(6) Uani 1 1 d . . .

loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_23
_atom_site_aniso_U_13
_atom_site_aniso_U_12
Cu1 0.0111(2) 0.01278(19) 0.0139(2) -0.00025(17) 0.00607(16) 0.00041(16)
N11 0.0105(15) 0.0147(14) 0.0130(15) 0.0039(11) 0.0050(12) 0.0026(11)
C12 0.016(2) 0.0115(16) 0.0144(18) 0.0048(13) 0.0059(15) 0.0022(13)
C13 0.013(2) 0.0234(18) 0.023(2) 0.0006(15) 0.0077(15) -0.0028(14)
C14 0.020(2) 0.0233(18) 0.022(2) -0.0041(16) 0.0007(17) -0.0010(16)
C15 0.025(2) 0.0211(18) 0.016(2) -0.0046(15) 0.0033(17) 0.0052(16)
C16 0.021(2) 0.0161(16) 0.0144(18) 0.0033(14) 0.0085(15) 0.0059(14)
C17 0.0150(19) 0.0169(16) 0.0205(19) -0.0003(14) 0.0105(15) 0.0005(14)
N18 0.0089(15) 0.0107(12) 0.0138(15) 0.0016(11) 0.0036(11) 0.0009(11)
C19 0.0177(19) 0.0127(15) 0.0112(17) -0.0008(13) 0.0088(14) 0.0050(14)
N21 0.0107(16) 0.0127(13) 0.0164(15) 0.0008(11) 0.0049(12) -0.0006(11)
C22 0.0167(19) 0.0074(15) 0.0128(18) 0.0022(13) 0.0036(15) 0.0023(13)
N23 0.0245(18) 0.0116(14) 0.0161(15) -0.0024(11) 0.0092(13) -0.0007(12)
C24 0.017(2) 0.0135(16) 0.0188(18) 0.0012(14) 0.0050(15) -0.0029(14)
C25 0.0107(19) 0.0170(16) 0.021(2) 0.0049(15) 0.0056(15) 0.0006(14)
N33 0.0148(16) 0.0176(14) 0.0150(15) 0.0017(12) 0.0058(12) 0.0056(12)
C32 0.0074(18) 0.0151(17) 0.0153(17) -0.0013(13) 0.0057(14) 0.0003(13)
N31 0.0133(16) 0.0135(14) 0.0152(15) -0.0005(11) 0.0063(12) 0.0017(11)
C35 0.0190(19) 0.0174(16) 0.0143(17) 0.0051(14) 0.0097(14) 0.0018(15)
C34 0.023(2) 0.0233(18) 0.0130(18) 0.0008(14) 0.0117(15) -0.0026(15)
O1 0.0143(15) 0.0297(15) 0.0305(16) 0.0170(12) 0.0076(12) 0.0016(12)
O2 0.0252(17) 0.0289(15) 0.0340(17) -0.0050(13) 0.0023(13) -0.0017(12)
O3 0.0345(17) 0.0259(15) 0.0248(15) 0.0026(11) 0.0132(12) -0.0006(12)
O4 0.0246(16) 0.0289(15) 0.0232(14) -0.0019(12) 0.0080(13) 0.0063(11)
O5 0.0264(17) 0.0397(17) 0.0222(16) 0.0036(13) 0.0091(13) 0.0030(12)
O6 0.0389(18) 0.0278(15) 0.0338(17) 0.0045(13) 0.0171(14) 0.0033(13)
Si1 0.0216(8) 0.0117(6) 0.0166(7) 0.000 0.0104(6) 0.000
F11 0.0299(12) 0.0402(12) 0.0200(11) 0.0054(9) 0.0070(9) -0.0016(9)
F12 0.0292(13) 0.0314(11) 0.0342(13) -0.0028(9) 0.0221(10) -0.0039(9)
F13 0.059(2) 0.0104(13) 0.0323(17) 0.000 0.0267(15) 0.000
F14 0.041(2) 0.0125(13) 0.052(2) 0.000 0.0262(16) 0.000
Si2 0.0106(7) 0.0150(6) 0.0183(7) 0.0012(5) 0.0046(6) 0.0019(5)
F21 0.0332(13) 0.0211(10) 0.0558(15) -0.0111(10) 0.0243(11) -0.0015(9)
F22 0.0162(11) 0.0268(10) 0.0382(13) 0.0073(9) 0.0133(9) 0.0026(8)
F23 0.0269(12) 0.0477(13) 0.0218(12) 0.0110(9) 0.0044(10) -0.0023(10)

_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 N21 1.981(2) . ?
Cu1 N31 1.997(3) 5_575 ?
Cu1 N11 1.999(2) . ?
Cu1 N18 2.032(3) . ?
Cu1 O1 2.257(2) . ?
N11 C16 1.350(4) . ?
N11 C12 1.355(4) . ?
C12 C13 1.386(4) . ?
C12 C17 1.502(4) . ?
C13 C14 1.386(5) . ?
C13 H13A 0.9500 . ?
C14 C15 1.369(5) . ?
C14 H14A 0.9500 . ?
C15 C16 1.388(4) . ?
C15 H15A 0.9500 . ?
C16 H16A 0.9500 . ?
C17 N18 1.482(4) . ?
C17 H17A 0.9900 . ?
C17 H17B 0.9900 . ?
N18 C19 1.512(4) . ?
N18 H18A 0.9300 . ?
C19 C22 1.490(4) . ?
C19 C32 1.502(4) . ?
C19 H19A 1.0000 . ?
N21 C22 1.325(4) . ?
N21 C25 1.394(4) . ?
C22 N23 1.348(4) . ?
N23 C24 1.373(4) . ?
N23 H23A 0.8800 . ?
C24 C25 1.355(4) . ?
C24 H24A 0.9500 . ?
C25 H25A 0.9500 . ?
N33 C32 1.339(4) . ?
N33 C34 1.365(4) . ?
N33 H33A 0.8800 . ?
C32 N31 1.344(4) . ?
N31 C35 1.391(4) . ?
N31 Cu1 1.997(3) 5_575 ?
C35 C34 1.344(4) . ?
C35 H35A 0.9500 . ?
C34 H34A 0.9500 . ?
O1 H1A 0.68(4) . ?
O1 H1B 0.82(3) . ?
O2 H21 0.76(4) . ?
O2 H22 0.75(4) . ?
O3 H31 0.84(4) . ?
O3 H32 0.81(4) . ?
O4 H41 0.80(4) . ?
O4 H42 0.77(4) . ?
O5 H5A 0.87(4) . ?
O5 H5B 0.78(4) . ?
O6 H61 0.78(4) . ?
O6 H62 0.83(4) . ?
Si1 F14 1.649(3) . ?
Si1 F12 1.675(2) . ?
Si1 F12 1.675(2) 2 ?
Si1 F13 1.692(3) . ?
Si1 F11 1.7094(18) 2 ?
Si1 F11 1.7095(18) . ?
Si2 F22 1.6787(19) 7_565 ?
Si2 F22 1.6788(19) . ?
Si2 F21 1.6874(17) 7_565 ?
Si2 F21 1.6874(17) . ?
Si2 F23 1.6921(18) 7_565 ?
Si2 F23 1.6922(18) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
N21 Cu1 N31 94.99(10) . 5_575 ?
N21 Cu1 N11 162.59(11) . . ?
N31 Cu1 N11 100.57(10) 5_575 . ?
N21 Cu1 N18 81.51(10) . . ?
N31 Cu1 N18 171.75(10) 5_575 . ?
N11 Cu1 N18 82.03(10) . . ?
N21 Cu1 O1 98.42(10) . . ?
N31 Cu1 O1 97.04(10) 5_575 . ?
N11 Cu1 O1 87.46(10) . . ?
N18 Cu1 O1 90.88(10) . . ?
C16 N11 C12 119.3(3) . . ?
C16 N11 Cu1 125.3(2) . . ?
C12 N11 Cu1 114.9(2) . . ?
N11 C12 C13 120.8(3) . . ?
N11 C12 C17 116.2(3) . . ?
C13 C12 C17 122.8(3) . . ?
C14 C13 C12 119.6(3) . . ?
C14 C13 H13A 120.2 . . ?
C12 C13 H13A 120.2 . . ?
C15 C14 C13 119.3(3) . . ?
C15 C14 H14A 120.4 . . ?
C13 C14 H14A 120.4 . . ?
C14 C15 C16 119.4(3) . . ?
C14 C15 H15A 120.3 . . ?
C16 C15 H15A 120.3 . . ?
N11 C16 C15 121.6(3) . . ?
N11 C16 H16A 119.2 . . ?
C15 C16 H16A 119.2 . . ?
N18 C17 C12 108.6(3) . . ?
N18 C17 H17A 110.0 . . ?
C12 C17 H17A 110.0 . . ?
N18 C17 H17B 110.0 . . ?
C12 C17 H17B 110.0 . . ?
H17A C17 H17B 108.4 . . ?
C17 N18 C19 117.3(2) . . ?
C17 N18 Cu1 111.10(18) . . ?
C19 N18 Cu1 112.09(18) . . ?
C17 N18 H18A 105.0 . . ?
C19 N18 H18A 105.0 . . ?
Cu1 N18 H18A 105.0 . . ?
C22 C19 C32 113.2(2) . . ?
C22 C19 N18 104.9(3) . . ?
C32 C19 N18 112.7(2) . . ?
C22 C19 H19A 108.6 . . ?
C32 C19 H19A 108.6 . . ?
N18 C19 H19A 108.6 . . ?
C22 N21 C25 105.9(3) . . ?
C22 N21 Cu1 113.8(2) . . ?
C25 N21 Cu1 140.2(2) . . ?
N21 C22 N23 110.8(3) . . ?
N21 C22 C19 121.5(3) . . ?
N23 C22 C19 127.7(3) . . ?
C22 N23 C24 107.7(3) . . ?
C22 N23 H23A 126.2 . . ?
C24 N23 H23A 126.2 . . ?
C25 C24 N23 106.7(3) . . ?
C25 C24 H24A 126.7 . . ?
N23 C24 H24A 126.7 . . ?
C24 C25 N21 108.9(3) . . ?
C24 C25 H25A 125.6 . . ?
N21 C25 H25A 125.6 . . ?
C32 N33 C34 108.2(3) . . ?
C32 N33 H33A 125.9 . . ?
C34 N33 H33A 125.9 . . ?
N33 C32 N31 110.1(3) . . ?
N33 C32 C19 121.7(3) . . ?
N31 C32 C19 128.1(3) . . ?
C32 N31 C35 105.6(3) . . ?
C32 N31 Cu1 133.7(2) . 5_575 ?
C35 N31 Cu1 119.86(19) . 5_575 ?
C34 C35 N31 109.0(3) . . ?
C34 C35 H35A 125.5 . . ?
N31 C35 H35A 125.5 . . ?
C35 C34 N33 107.2(3) . . ?
C35 C34 H34A 126.4 . . ?
N33 C34 H34A 126.4 . . ?
Cu1 O1 H1A 135(4) . . ?
Cu1 O1 H1B 116(3) . . ?
H1A O1 H1B 109(4) . . ?
H21 O2 H22 106(4) . . ?
H31 O3 H32 103(4) . . ?
H41 O4 H42 107(4) . . ?
H5A O5 H5B 97(4) . . ?
H61 O6 H62 112(4) . . ?
F14 Si1 F12 91.83(7) . . ?
F14 Si1 F12 91.83(7) . 2 ?
F12 Si1 F12 176.34(14) . 2 ?
F14 Si1 F13 180.000(1) . . ?
F12 Si1 F13 88.17(7) . . ?
F12 Si1 F13 88.17(7) 2 . ?
F14 Si1 F11 91.01(7) . 2 ?
F12 Si1 F11 89.17(10) . 2 ?
F12 Si1 F11 90.76(10) 2 2 ?
F13 Si1 F11 88.99(7) . 2 ?
F14 Si1 F11 91.01(7) . . ?
F12 Si1 F11 90.76(10) . . ?
F12 Si1 F11 89.17(10) 2 . ?
F13 Si1 F11 88.99(7) . . ?
F11 Si1 F11 177.97(14) 2 . ?
F22 Si2 F22 180.00(13) 7_565 . ?
F22 Si2 F21 90.86(9) 7_565 7_565 ?
F22 Si2 F21 89.14(9) . 7_565 ?
F22 Si2 F21 89.14(9) 7_565 . ?
F22 Si2 F21 90.86(9) . . ?
F21 Si2 F21 180.0 7_565 . ?
F22 Si2 F23 91.42(9) 7_565 7_565 ?
F22 Si2 F23 88.58(9) . 7_565 ?
F21 Si2 F23 90.59(10) 7_565 7_565 ?
F21 Si2 F23 89.41(10) . 7_565 ?
F22 Si2 F23 88.58(9) 7_565 . ?
F22 Si2 F23 91.42(9) . . ?
F21 Si2 F23 89.41(10) 7_565 . ?
F21 Si2 F23 90.59(10) . . ?
F23 Si2 F23 180.0 7_565 . ?

_diffrn_measured_fraction_theta_max 0.981
_diffrn_reflns_theta_full        25.50
_diffrn_measured_fraction_theta_full 0.981
_refine_diff_density_max         0.397
_refine_diff_density_min         -0.465
_refine_diff_density_rms         0.082

#===END

data_2
_database_code_depnum_ccdc_archive 'CCDC 826232'
#TrackingRef '- cif data_song_ICpaper.cif'

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C30 H36 Cl2 Cu3 N12 O20'
_chemical_formula_weight         1146.23

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'
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'

_symmetry_cell_setting           Monoclinic
_symmetry_space_group_name_H-M   P2(1)/n

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

_cell_length_a                   10.1448(17)
_cell_length_b                   16.441(2)
_cell_length_c                   13.180(2)
_cell_angle_alpha                90.00
_cell_angle_beta                 109.542(2)
_cell_angle_gamma                90.00
_cell_volume                     2071.7(6)
_cell_formula_units_Z            2
_cell_measurement_temperature    93(2)
_cell_measurement_reflns_used    6527
_cell_measurement_theta_min      3.09
_cell_measurement_theta_max      27.48

_exptl_crystal_description       Prism
_exptl_crystal_colour            Blue
_exptl_crystal_size_max          0.33
_exptl_crystal_size_mid          0.17
_exptl_crystal_size_min          0.13
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.838
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1162
_exptl_absorpt_coefficient_mu    1.752
_exptl_absorpt_correction_type   Empirical
_exptl_absorpt_correction_T_min  0.5931
_exptl_absorpt_correction_T_max  0.8004
_exptl_absorpt_process_details   ?

_exptl_special_details           
;
?
;

_diffrn_ambient_temperature      93(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'Rotating Anode'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  AFC10/Saturn724+
_diffrn_measurement_method       Multi-scan
_diffrn_detector_area_resol_mean 28.5714
_diffrn_standards_number         0
_diffrn_standards_interval_count 0
_diffrn_standards_interval_time  0
_diffrn_standards_decay_%        0
_diffrn_reflns_number            16527
_diffrn_reflns_av_R_equivalents  0.0347
_diffrn_reflns_av_sigmaI/netI    0.0354
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_k_min       -21
_diffrn_reflns_limit_k_max       21
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_theta_min         3.09
_diffrn_reflns_theta_max         27.48
_reflns_number_total             4720
_reflns_number_gt                4116
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'CrystalClear (Rigaku Inc., 2008)'
_computing_cell_refinement       'CrystalClear (Rigaku Inc., 2008)'
_computing_data_reduction        'CrystalClear (Rigaku Inc., 2008)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_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^)+(0.0286P)^2^+1.6900P] where P=(Fo^2^+2Fc^2^)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         4720
_refine_ls_number_parameters     324
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0378
_refine_ls_R_factor_gt           0.0289
_refine_ls_wR_factor_ref         0.0672
_refine_ls_wR_factor_gt          0.0635
_refine_ls_goodness_of_fit_ref   0.999
_refine_ls_restrained_S_all      0.999
_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 0.64364(2) 0.518543(15) 0.958664(19) 0.00814(7) Uani 1 1 d . . .
Cu2 Cu 0.5000 0.5000 0.5000 0.00974(9) Uani 1 2 d S . .
Cl1 Cl 0.28418(5) 0.67806(3) 0.47793(4) 0.01305(11) Uani 1 1 d . . .
O1 O 0.78351(17) 0.59498(10) 0.89206(13) 0.0147(3) Uani 1 1 d . . .
O2 O 0.63314(15) 0.53332(9) 0.64026(11) 0.0122(3) Uani 1 1 d . . .
O3 O 0.85168(15) 0.58160(9) 0.70808(11) 0.0144(3) Uani 1 1 d . . .
O4 O 0.64302(14) 0.53476(9) 0.44353(11) 0.0108(3) Uani 1 1 d . . .
O5 O 0.86526(15) 0.57635(9) 0.50128(11) 0.0146(3) Uani 1 1 d . . .
O6 O 0.40175(16) 0.63792(9) 0.45946(13) 0.0198(4) Uani 1 1 d . . .
O7 O 0.17891(15) 0.61897(9) 0.47837(12) 0.0169(3) Uani 1 1 d . . .
O8 O 0.33103(18) 0.72014(11) 0.57903(13) 0.0259(4) Uani 1 1 d . . .
O9 O 0.22463(18) 0.73516(10) 0.39103(13) 0.0229(4) Uani 1 1 d . . .
N1 N 0.72966(17) 0.41220(10) 0.94445(13) 0.0096(3) Uani 1 1 d . . .
N2 N 0.51516(18) 0.48987(10) 0.80738(14) 0.0089(3) Uani 1 1 d . . .
N3 N 0.24438(17) 0.45880(10) 0.88803(13) 0.0091(3) Uani 1 1 d . . .
N4 N 0.16163(18) 0.44249(11) 0.71263(14) 0.0115(4) Uani 1 1 d . . .
H4N H 0.1527 0.4466 0.6441 0.014 Uiso 1 1 calc R . .
N5 N 0.51129(17) 0.60992(10) 0.93937(13) 0.0090(3) Uani 1 1 d . . .
N6 N 0.32444(18) 0.67267(10) 0.83330(14) 0.0108(3) Uani 1 1 d . . .
H6N H 0.2471 0.6823 0.7792 0.013 Uiso 1 1 calc R . .
C1 C 0.8514(2) 0.38278(13) 1.01223(17) 0.0126(4) Uani 1 1 d . . .
H1 H 0.9017 0.4138 1.0738 0.015 Uiso 1 1 calc R . .
C2 C 0.9049(2) 0.30933(13) 0.99494(18) 0.0149(4) Uani 1 1 d . . .
H2 H 0.9890 0.2890 1.0454 0.018 Uiso 1 1 calc R . .
C3 C 0.8350(2) 0.26510(13) 0.90322(18) 0.0157(4) Uani 1 1 d . . .
H3 H 0.8723 0.2152 0.8886 0.019 Uiso 1 1 calc R . .
C4 C 0.7098(2) 0.29497(13) 0.83296(18) 0.0141(4) Uani 1 1 d . . .
H4 H 0.6597 0.2657 0.7696 0.017 Uiso 1 1 calc R . .
C5 C 0.6589(2) 0.36812(12) 0.85678(16) 0.0100(4) Uani 1 1 d . . .
C6 C 0.5192(2) 0.40162(12) 0.78764(16) 0.0106(4) Uani 1 1 d . . .
H6A H 0.5055 0.3917 0.7107 0.013 Uiso 1 1 calc R . .
H6B H 0.4430 0.3740 0.8054 0.013 Uiso 1 1 calc R . .
C7 C 0.3743(2) 0.53023(12) 0.77844(16) 0.0091(4) Uani 1 1 d . . .
H7 H 0.3442 0.5477 0.7014 0.011 Uiso 1 1 calc R . .
C8 C 0.2627(2) 0.47743(12) 0.79499(16) 0.0090(4) Uani 1 1 d . . .
C9 C 0.1269(2) 0.40968(13) 0.86189(17) 0.0125(4) Uani 1 1 d . . .
H9 H 0.0885 0.3866 0.9119 0.015 Uiso 1 1 calc R . .
C10 C 0.0753(2) 0.39961(13) 0.75348(17) 0.0139(4) Uani 1 1 d . . .
H10 H -0.0047 0.3689 0.7139 0.017 Uiso 1 1 calc R . .
C11 C 0.4008(2) 0.60466(12) 0.84914(16) 0.0095(4) Uani 1 1 d . . .
C12 C 0.5039(2) 0.68586(12) 0.98164(16) 0.0112(4) Uani 1 1 d . . .
H12 H 0.5692 0.7073 1.0457 0.013 Uiso 1 1 calc R . .
C13 C 0.3887(2) 0.72500(13) 0.91709(17) 0.0124(4) Uani 1 1 d . . .
H13 H 0.3583 0.7780 0.9275 0.015 Uiso 1 1 calc R . .
C14 C 0.7499(2) 0.55730(12) 0.63267(16) 0.0103(4) Uani 1 1 d . . .
C15 C 0.7568(2) 0.55606(12) 0.51665(16) 0.0104(4) Uani 1 1 d . . .
O10 O 1.08004(18) 0.66292(11) 0.66698(15) 0.0197(4) Uani 1 1 d . . .
H2N H 0.556(3) 0.5137(14) 0.7723(19) 0.010(6) Uiso 1 1 d . . .
H01A H 0.800(3) 0.5869(18) 0.838(2) 0.034(9) Uiso 1 1 d . . .
H01B H 0.762(3) 0.644(2) 0.891(2) 0.035(9) Uiso 1 1 d . . .
H00A H 1.084(3) 0.649(2) 0.614(3) 0.038(10) Uiso 1 1 d . . .
H00B H 1.016(4) 0.639(2) 0.673(3) 0.050(11) Uiso 1 1 d . . .

loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_23
_atom_site_aniso_U_13
_atom_site_aniso_U_12
Cu1 0.00807(12) 0.00988(13) 0.00657(13) -0.00095(9) 0.00259(9) -0.00013(9)
Cu2 0.00867(17) 0.01410(19) 0.00704(18) -0.00105(13) 0.00342(14) -0.00191(13)
Cl1 0.0125(2) 0.0113(2) 0.0171(3) -0.00144(19) 0.0073(2) -0.00089(18)
O1 0.0186(8) 0.0165(9) 0.0114(8) -0.0011(7) 0.0083(7) -0.0038(6)
O2 0.0114(7) 0.0178(8) 0.0084(7) -0.0019(6) 0.0046(6) -0.0034(6)
O3 0.0126(7) 0.0213(8) 0.0097(7) -0.0023(6) 0.0044(6) -0.0045(6)
O4 0.0106(7) 0.0146(7) 0.0075(7) 0.0000(6) 0.0035(6) -0.0008(6)
O5 0.0132(7) 0.0219(8) 0.0103(7) -0.0023(6) 0.0062(6) -0.0060(6)
O6 0.0155(8) 0.0150(8) 0.0331(10) 0.0014(7) 0.0137(7) 0.0037(6)
O7 0.0128(7) 0.0169(8) 0.0209(9) 0.0009(6) 0.0052(6) -0.0043(6)
O8 0.0252(9) 0.0325(10) 0.0210(9) -0.0141(8) 0.0090(8) -0.0104(7)
O9 0.0262(9) 0.0182(8) 0.0288(10) 0.0100(7) 0.0152(8) 0.0075(7)
N1 0.0094(8) 0.0103(8) 0.0101(9) 0.0009(7) 0.0046(7) -0.0001(6)
N2 0.0084(8) 0.0106(9) 0.0091(9) 0.0005(7) 0.0050(7) -0.0003(6)
N3 0.0093(8) 0.0104(8) 0.0076(8) -0.0007(7) 0.0026(7) -0.0007(6)
N4 0.0129(9) 0.0151(9) 0.0071(9) -0.0018(7) 0.0041(7) -0.0025(7)
N5 0.0098(8) 0.0105(8) 0.0069(8) 0.0002(7) 0.0031(7) -0.0002(6)
N6 0.0101(8) 0.0117(9) 0.0102(9) 0.0013(7) 0.0031(7) 0.0008(6)
C1 0.0099(10) 0.0153(11) 0.0124(11) -0.0005(8) 0.0033(8) -0.0019(8)
C2 0.0110(10) 0.0167(11) 0.0167(11) 0.0031(9) 0.0045(9) 0.0013(8)
C3 0.0144(10) 0.0131(11) 0.0226(12) -0.0021(9) 0.0102(9) 0.0012(8)
C4 0.0144(10) 0.0139(10) 0.0156(11) -0.0035(8) 0.0071(9) -0.0018(8)
C5 0.0108(9) 0.0112(10) 0.0102(10) 0.0019(8) 0.0064(8) 0.0003(8)
C6 0.0121(10) 0.0093(10) 0.0101(10) -0.0012(8) 0.0034(8) 0.0003(7)
C7 0.0100(9) 0.0103(10) 0.0076(10) 0.0004(8) 0.0037(8) 0.0008(7)
C8 0.0086(9) 0.0101(10) 0.0083(10) -0.0011(8) 0.0029(8) 0.0003(7)
C9 0.0095(10) 0.0165(11) 0.0122(11) -0.0004(8) 0.0046(8) -0.0034(8)
C10 0.0118(10) 0.0160(11) 0.0138(11) -0.0028(8) 0.0041(9) -0.0051(8)
C11 0.0094(9) 0.0112(10) 0.0096(10) 0.0008(8) 0.0055(8) -0.0002(7)
C12 0.0131(10) 0.0118(10) 0.0105(10) -0.0029(8) 0.0064(8) -0.0036(8)
C13 0.0165(10) 0.0102(10) 0.0131(11) -0.0027(8) 0.0082(9) -0.0027(8)
C14 0.0117(10) 0.0101(10) 0.0099(10) 0.0010(8) 0.0048(8) 0.0009(7)
C15 0.0127(10) 0.0085(10) 0.0101(10) 0.0003(8) 0.0042(8) 0.0010(7)
O10 0.0147(8) 0.0266(9) 0.0162(10) -0.0016(7) 0.0033(7) -0.0074(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 N5 1.9738(17) . ?
Cu1 N1 1.9906(17) . ?
Cu1 N3 1.9941(17) 3_667 ?
Cu1 N2 2.0392(18) . ?
Cu1 O1 2.2796(16) . ?
Cu2 O4 1.9256(14) 3_666 ?
Cu2 O4 1.9256(14) . ?
Cu2 O2 1.9676(14) . ?
Cu2 O2 1.9676(14) 3_666 ?
Cl1 O8 1.4341(17) . ?
Cl1 O7 1.4451(15) . ?
Cl1 O9 1.4475(16) . ?
Cl1 O6 1.4532(15) . ?
O1 H01A 0.80(3) . ?
O1 H01B 0.83(3) . ?
O2 C14 1.284(2) . ?
O3 C14 1.236(2) . ?
O4 C15 1.281(2) . ?
O5 C15 1.230(2) . ?
N1 C1 1.349(3) . ?
N1 C5 1.349(3) . ?
N2 C6 1.477(3) . ?
N2 C7 1.504(3) . ?
N2 H2N 0.82(3) . ?
N3 C8 1.336(3) . ?
N3 C9 1.384(3) . ?
N3 Cu1 1.9941(17) 3_667 ?
N4 C8 1.347(3) . ?
N4 C10 1.367(3) . ?
N4 H4N 0.8800 . ?
N5 C11 1.337(3) . ?
N5 C12 1.379(3) . ?
N6 C11 1.336(3) . ?
N6 C13 1.380(3) . ?
N6 H6N 0.8800 . ?
C1 C2 1.374(3) . ?
C1 H1 0.9500 . ?
C2 C3 1.385(3) . ?
C2 H2 0.9500 . ?
C3 C4 1.388(3) . ?
C3 H3 0.9500 . ?
C4 C5 1.386(3) . ?
C4 H4 0.9500 . ?
C5 C6 1.510(3) . ?
C6 H6A 0.9900 . ?
C6 H6B 0.9900 . ?
C7 C8 1.500(3) . ?
C7 C11 1.507(3) . ?
C7 H7 1.0000 . ?
C9 C10 1.357(3) . ?
C9 H9 0.9500 . ?
C10 H10 0.9500 . ?
C12 C13 1.356(3) . ?
C12 H12 0.9500 . ?
C13 H13 0.9500 . ?
C14 C15 1.554(3) . ?
O10 H00A 0.75(3) . ?
O10 H00B 0.78(4) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
N5 Cu1 N1 163.15(7) . . ?
N5 Cu1 N3 96.94(7) . 3_667 ?
N1 Cu1 N3 98.07(7) . 3_667 ?
N5 Cu1 N2 82.25(7) . . ?
N1 Cu1 N2 82.06(7) . . ?
N3 Cu1 N2 174.35(7) 3_667 . ?
N5 Cu1 O1 90.86(7) . . ?
N1 Cu1 O1 95.68(7) . . ?
N3 Cu1 O1 94.03(6) 3_667 . ?
N2 Cu1 O1 91.58(7) . . ?
O4 Cu2 O4 180.0 3_666 . ?
O4 Cu2 O2 95.09(6) 3_666 . ?
O4 Cu2 O2 84.91(6) . . ?
O4 Cu2 O2 84.91(6) 3_666 3_666 ?
O4 Cu2 O2 95.09(6) . 3_666 ?
O2 Cu2 O2 180.00(6) . 3_666 ?
O8 Cl1 O7 109.66(10) . . ?
O8 Cl1 O9 110.07(11) . . ?
O7 Cl1 O9 109.01(10) . . ?
O8 Cl1 O6 109.83(10) . . ?
O7 Cl1 O6 110.14(9) . . ?
O9 Cl1 O6 108.10(10) . . ?
Cu1 O1 H01A 127(2) . . ?
Cu1 O1 H01B 110(2) . . ?
H01A O1 H01B 106(3) . . ?
C14 O2 Cu2 111.94(13) . . ?
C15 O4 Cu2 113.35(12) . . ?
C1 N1 C5 118.78(17) . . ?
C1 N1 Cu1 125.86(14) . . ?
C5 N1 Cu1 115.34(13) . . ?
C6 N2 C7 117.93(16) . . ?
C6 N2 Cu1 110.68(12) . . ?
C7 N2 Cu1 112.85(12) . . ?
C6 N2 H2N 108.8(16) . . ?
C7 N2 H2N 105.4(17) . . ?
Cu1 N2 H2N 99.3(17) . . ?
C8 N3 C9 106.12(17) . . ?
C8 N3 Cu1 132.88(14) . 3_667 ?
C9 N3 Cu1 120.82(13) . 3_667 ?
C8 N4 C10 108.51(17) . . ?
C8 N4 H4N 125.7 . . ?
C10 N4 H4N 125.7 . . ?
C11 N5 C12 105.98(17) . . ?
C11 N5 Cu1 113.41(13) . . ?
C12 N5 Cu1 139.75(14) . . ?
C11 N6 C13 107.62(17) . . ?
C11 N6 H6N 126.2 . . ?
C13 N6 H6N 126.2 . . ?
N1 C1 C2 122.0(2) . . ?
N1 C1 H1 119.0 . . ?
C2 C1 H1 119.0 . . ?
C1 C2 C3 119.4(2) . . ?
C1 C2 H2 120.3 . . ?
C3 C2 H2 120.3 . . ?
C2 C3 C4 118.9(2) . . ?
C2 C3 H3 120.6 . . ?
C4 C3 H3 120.6 . . ?
C5 C4 C3 118.9(2) . . ?
C5 C4 H4 120.6 . . ?
C3 C4 H4 120.6 . . ?
N1 C5 C4 121.91(19) . . ?
N1 C5 C6 116.36(17) . . ?
C4 C5 C6 121.71(19) . . ?
N2 C6 C5 109.13(16) . . ?
N2 C6 H6A 109.9 . . ?
C5 C6 H6A 109.9 . . ?
N2 C6 H6B 109.9 . . ?
C5 C6 H6B 109.9 . . ?
H6A C6 H6B 108.3 . . ?
C8 C7 N2 114.04(16) . . ?
C8 C7 C11 111.55(16) . . ?
N2 C7 C11 104.10(16) . . ?
C8 C7 H7 109.0 . . ?
N2 C7 H7 109.0 . . ?
C11 C7 H7 109.0 . . ?
N3 C8 N4 109.89(17) . . ?
N3 C8 C7 127.58(18) . . ?
N4 C8 C7 122.53(18) . . ?
C10 C9 N3 109.26(18) . . ?
C10 C9 H9 125.4 . . ?
N3 C9 H9 125.4 . . ?
C9 C10 N4 106.23(18) . . ?
C9 C10 H10 126.9 . . ?
N4 C10 H10 126.9 . . ?
N6 C11 N5 110.77(18) . . ?
N6 C11 C7 127.50(18) . . ?
N5 C11 C7 121.72(18) . . ?
C13 C12 N5 109.14(18) . . ?
C13 C12 H12 125.4 . . ?
N5 C12 H12 125.4 . . ?
C12 C13 N6 106.48(18) . . ?
C12 C13 H13 126.8 . . ?
N6 C13 H13 126.8 . . ?
O3 C14 O2 125.54(19) . . ?
O3 C14 C15 119.67(18) . . ?
O2 C14 C15 114.78(17) . . ?
O5 C15 O4 125.54(19) . . ?
O5 C15 C14 119.73(18) . . ?
O4 C15 C14 114.71(17) . . ?
H00A O10 H00B 104(3) . . ?

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 Cu2 O2 C14 176.65(14) 3_666 . . . ?
O4 Cu2 O2 C14 -3.34(14) . . . . ?
O2 Cu2 O2 C14 114(4) 3_666 . . . ?
O4 Cu2 O4 C15 -111(10) 3_666 . . . ?
O2 Cu2 O4 C15 5.13(14) . . . . ?
O2 Cu2 O4 C15 -174.86(14) 3_666 . . . ?
N5 Cu1 N1 C1 -168.7(2) . . . . ?
N3 Cu1 N1 C1 -16.00(17) 3_667 . . . ?
N2 Cu1 N1 C1 169.70(17) . . . . ?
O1 Cu1 N1 C1 78.90(17) . . . . ?
N5 Cu1 N1 C5 13.1(3) . . . . ?
N3 Cu1 N1 C5 165.81(14) 3_667 . . . ?
N2 Cu1 N1 C5 -8.49(14) . . . . ?
O1 Cu1 N1 C5 -99.30(14) . . . . ?
N5 Cu1 N2 C6 -153.58(14) . . . . ?
N1 Cu1 N2 C6 20.25(13) . . . . ?
N3 Cu1 N2 C6 -71.4(7) 3_667 . . . ?
O1 Cu1 N2 C6 115.76(13) . . . . ?
N5 Cu1 N2 C7 -18.97(13) . . . . ?
N1 Cu1 N2 C7 154.86(14) . . . . ?
N3 Cu1 N2 C7 63.2(8) 3_667 . . . ?
O1 Cu1 N2 C7 -109.62(13) . . . . ?
N1 Cu1 N5 C11 -14.8(3) . . . . ?
N3 Cu1 N5 C11 -167.57(14) 3_667 . . . ?
N2 Cu1 N5 C11 6.79(14) . . . . ?
O1 Cu1 N5 C11 98.26(14) . . . . ?
N1 Cu1 N5 C12 177.8(2) . . . . ?
N3 Cu1 N5 C12 25.0(2) 3_667 . . . ?
N2 Cu1 N5 C12 -160.6(2) . . . . ?
O1 Cu1 N5 C12 -69.1(2) . . . . ?
C5 N1 C1 C2 -0.3(3) . . . . ?
Cu1 N1 C1 C2 -178.48(15) . . . . ?
N1 C1 C2 C3 2.5(3) . . . . ?
C1 C2 C3 C4 -2.3(3) . . . . ?
C2 C3 C4 C5 0.2(3) . . . . ?
C1 N1 C5 C4 -1.9(3) . . . . ?
Cu1 N1 C5 C4 176.40(15) . . . . ?
C1 N1 C5 C6 176.37(18) . . . . ?
Cu1 N1 C5 C6 -5.3(2) . . . . ?
C3 C4 C5 N1 2.0(3) . . . . ?
C3 C4 C5 C6 -176.20(19) . . . . ?
C7 N2 C6 C5 -159.33(16) . . . . ?
Cu1 N2 C6 C5 -27.27(18) . . . . ?
N1 C5 C6 N2 21.8(2) . . . . ?
C4 C5 C6 N2 -159.88(18) . . . . ?
C6 N2 C7 C8 34.2(2) . . . . ?
Cu1 N2 C7 C8 -96.84(17) . . . . ?
C6 N2 C7 C11 156.02(16) . . . . ?
Cu1 N2 C7 C11 24.94(18) . . . . ?
C9 N3 C8 N4 0.3(2) . . . . ?
Cu1 N3 C8 N4 175.29(14) 3_667 . . . ?
C9 N3 C8 C7 179.09(19) . . . . ?
Cu1 N3 C8 C7 -6.0(3) 3_667 . . . ?
C10 N4 C8 N3 -0.2(2) . . . . ?
C10 N4 C8 C7 -179.05(18) . . . . ?
N2 C7 C8 N3 76.4(3) . . . . ?
C11 C7 C8 N3 -41.2(3) . . . . ?
N2 C7 C8 N4 -105.0(2) . . . . ?
C11 C7 C8 N4 137.42(19) . . . . ?
C8 N3 C9 C10 -0.3(2) . . . . ?
Cu1 N3 C9 C10 -176.03(14) 3_667 . . . ?
N3 C9 C10 N4 0.2(2) . . . . ?
C8 N4 C10 C9 0.0(2) . . . . ?
C13 N6 C11 N5 0.3(2) . . . . ?
C13 N6 C11 C7 -178.97(19) . . . . ?
C12 N5 C11 N6 -0.5(2) . . . . ?
Cu1 N5 C11 N6 -172.09(13) . . . . ?
C12 N5 C11 C7 178.78(17) . . . . ?
Cu1 N5 C11 C7 7.2(2) . . . . ?
C8 C7 C11 N6 -78.8(3) . . . . ?
N2 C7 C11 N6 157.76(19) . . . . ?
C8 C7 C11 N5 102.0(2) . . . . ?
N2 C7 C11 N5 -21.4(2) . . . . ?
C11 N5 C12 C13 0.6(2) . . . . ?
Cu1 N5 C12 C13 168.55(16) . . . . ?
N5 C12 C13 N6 -0.4(2) . . . . ?
C11 N6 C13 C12 0.1(2) . . . . ?
Cu2 O2 C14 O3 179.90(17) . . . . ?
Cu2 O2 C14 C15 1.2(2) . . . . ?
Cu2 O4 C15 O5 175.94(17) . . . . ?
Cu2 O4 C15 C14 -5.7(2) . . . . ?
O3 C14 C15 O5 2.7(3) . . . . ?
O2 C14 C15 O5 -178.51(18) . . . . ?
O3 C14 C15 O4 -175.77(18) . . . . ?
O2 C14 C15 O4 3.0(3) . . . . ?

_diffrn_measured_fraction_theta_max 0.995
_diffrn_reflns_theta_full        27.48
_diffrn_measured_fraction_theta_full 0.995
_refine_diff_density_max         0.441
_refine_diff_density_min         -0.460
_refine_diff_density_rms         0.076

#===END

data_3
_database_code_depnum_ccdc_archive 'CCDC 826233'
#TrackingRef '- cif data_song_ICpaper.cif'

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C12 H22 Cl Cu N5 O11'
_chemical_formula_weight         511.34

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'
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'

_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                   7.6833(18)
_cell_length_b                   9.5255(19)
_cell_length_c                   13.551(4)
_cell_angle_alpha                85.330(7)
_cell_angle_beta                 87.060(6)
_cell_angle_gamma                80.222(7)
_cell_volume                     973.4(4)
_cell_formula_units_Z            2
_cell_measurement_temperature    93(2)
_cell_measurement_reflns_used    3354
_cell_measurement_theta_min      3.02
_cell_measurement_theta_max      27.50

_exptl_crystal_description       Block
_exptl_crystal_colour            Blue
_exptl_crystal_size_max          0.40
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.17
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.745
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             526
_exptl_absorpt_coefficient_mu    1.328
_exptl_absorpt_correction_type   Empirical
_exptl_absorpt_correction_T_min  0.6186
_exptl_absorpt_correction_T_max  0.8086
_exptl_absorpt_process_details   ?

_exptl_special_details           
;
?
;

_diffrn_ambient_temperature      93(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'Rotating Anode'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  AFC10/Saturn724+
_diffrn_measurement_method       Multi-scan
_diffrn_detector_area_resol_mean 28.5714
_diffrn_standards_number         0
_diffrn_standards_interval_count 0
_diffrn_standards_interval_time  0
_diffrn_standards_decay_%        0
_diffrn_reflns_number            9849
_diffrn_reflns_av_R_equivalents  0.0252
_diffrn_reflns_av_sigmaI/netI    0.0368
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_theta_min         3.02
_diffrn_reflns_theta_max         27.48
_reflns_number_total             4417
_reflns_number_gt                3835
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'CrystalClear (Rigaku Inc., 2008)'
_computing_cell_refinement       'CrystalClear (Rigaku Inc., 2008)'
_computing_data_reduction        'CrystalClear (Rigaku Inc., 2008)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_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^)+(0.0366P)^2^+0.3600P] where P=(Fo^2^+2Fc^2^)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         4417
_refine_ls_number_parameters     313
_refine_ls_number_restraints     9
_refine_ls_R_factor_all          0.0335
_refine_ls_R_factor_gt           0.0277
_refine_ls_wR_factor_ref         0.0714
_refine_ls_wR_factor_gt          0.0693
_refine_ls_goodness_of_fit_ref   1.003
_refine_ls_restrained_S_all      1.002
_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 0.30413(3) 0.48816(2) 0.669218(15) 0.00932(7) Uani 1 1 d . . .
O1 O 0.39755(17) 0.29482(13) 0.72271(9) 0.0105(3) Uani 1 1 d . . .
O2 O 0.47306(17) 0.07501(13) 0.67016(10) 0.0135(3) Uani 1 1 d . . .
O3 O 0.29356(18) 0.39849(13) 0.54524(9) 0.0125(3) Uani 1 1 d . . .
O4 O 0.32455(18) 0.17874(14) 0.49202(9) 0.0141(3) Uani 1 1 d . . .
O5 O 0.61283(18) 0.52077(14) 0.64504(10) 0.0130(3) Uani 1 1 d D . .
N1 N 0.2259(2) 0.68142(16) 0.60496(11) 0.0100(3) Uani 1 1 d . . .
N2 N 0.2501(2) 0.90434(17) 0.56096(11) 0.0106(3) Uani 1 1 d . . .
N3 N 0.2928(2) 0.57196(16) 0.79778(11) 0.0108(3) Uani 1 1 d . . .
N4 N 0.2604(2) 0.73999(18) 0.90217(11) 0.0124(3) Uani 1 1 d . . .
N5 N 0.5599(2) 0.78769(18) 0.71527(11) 0.0100(3) Uani 1 1 d . . .
C1 C 0.1565(2) 0.7179(2) 0.51256(13) 0.0125(4) Uani 1 1 d . . .
H1 H 0.1061 0.6566 0.4746 0.015 Uiso 1 1 calc R . .
C2 C 0.1719(2) 0.8554(2) 0.48485(13) 0.0127(4) Uani 1 1 d . . .
H2 H 0.1357 0.9075 0.4245 0.015 Uiso 1 1 calc R . .
C3 C 0.2801(2) 0.79785(19) 0.63210(13) 0.0094(3) Uani 1 1 d . . .
C4 C 0.2439(3) 0.5154(2) 0.88949(13) 0.0148(4) Uani 1 1 d . . .
H4 H 0.2269 0.4194 0.9048 0.018 Uiso 1 1 calc R . .
C5 C 0.2236(3) 0.6186(2) 0.95484(14) 0.0164(4) Uani 1 1 d . . .
H5 H 0.1905 0.6086 1.0232 0.020 Uiso 1 1 calc R . .
C6 C 0.3030(2) 0.70785(19) 0.80797(13) 0.0102(4) Uani 1 1 d . . .
C7 C 0.3599(2) 0.81033(19) 0.72917(13) 0.0094(3) Uani 1 1 d . . .
H7 H 0.3190 0.9093 0.7498 0.011 Uiso 1 1 calc R . .
C8 C 0.6617(2) 0.8075(2) 0.80459(13) 0.0128(4) Uani 1 1 d . . .
H8 H 0.5853 0.8759 0.8473 0.015 Uiso 1 1 calc R . .
C9 C 0.8234(3) 0.8717(2) 0.76737(16) 0.0203(4) Uani 1 1 d . . .
H9A H 0.8936 0.8830 0.8237 0.024 Uiso 1 1 calc R . .
H9B H 0.7855 0.9653 0.7324 0.024 Uiso 1 1 calc R . .
H9C H 0.8953 0.8083 0.7220 0.024 Uiso 1 1 calc R . .
C10 C 0.7127(3) 0.6662(2) 0.86457(14) 0.0181(4) Uani 1 1 d . . .
H10A H 0.6062 0.6255 0.8842 0.022 Uiso 1 1 calc R . .
H10B H 0.7726 0.6818 0.9239 0.022 Uiso 1 1 calc R . .
H10C H 0.7924 0.6000 0.8243 0.022 Uiso 1 1 calc R . .
C11 C 0.4095(2) 0.2022(2) 0.65806(13) 0.0107(4) Uani 1 1 d . . .
C12 C 0.3360(2) 0.26206(19) 0.55548(13) 0.0107(4) Uani 1 1 d . . .
Cl1 Cl -0.03641(6) 0.25894(5) 0.76217(3) 0.01387(11) Uani 1 1 d . . .
O6 O 0.00394(19) 0.39435(16) 0.71886(12) 0.0243(3) Uani 1 1 d . . .
O7 O 0.06448(19) 0.14315(15) 0.71133(11) 0.0194(3) Uani 1 1 d . . .
O8 O -0.22296(19) 0.26060(16) 0.75295(12) 0.0251(3) Uani 1 1 d . . .
O9 O 0.0072(2) 0.24283(17) 0.86496(11) 0.0301(4) Uani 1 1 d . . .
O10 O 0.5016(2) 0.16216(17) 0.90900(11) 0.0226(3) Uani 1 1 d D . .
O11 O 0.2370(2) 0.01247(15) 0.96341(11) 0.0205(3) Uani 1 1 d D . .
H2N H 0.284(3) 0.986(3) 0.560(2) 0.034(7) Uiso 1 1 d . . .
H4N H 0.259(3) 0.820(3) 0.9215(17) 0.020(6) Uiso 1 1 d . . .
H5A H 0.594(3) 0.695(3) 0.6947(18) 0.030(7) Uiso 1 1 d . . .
H5B H 0.580(3) 0.847(3) 0.6662(18) 0.022(6) Uiso 1 1 d . . .
H00A H 0.486(3) 0.207(3) 0.8555(12) 0.050(9) Uiso 1 1 d D . .
H00B H 0.6053(17) 0.126(3) 0.9136(19) 0.045(9) Uiso 1 1 d D . .
H01A H 0.1493(19) 0.063(2) 0.9411(18) 0.031(7) Uiso 1 1 d D . .
H01B H 0.323(2) 0.051(3) 0.949(2) 0.049(9) Uiso 1 1 d D . .
H05A H 0.664(3) 0.4474(18) 0.6734(16) 0.038(8) Uiso 1 1 d D . .
H05B H 0.658(4) 0.531(3) 0.5895(10) 0.052(9) Uiso 1 1 d D . .

loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_23
_atom_site_aniso_U_13
_atom_site_aniso_U_12
Cu1 0.01323(12) 0.00596(12) 0.00861(11) -0.00068(8) -0.00004(8) -0.00124(8)
O1 0.0123(6) 0.0071(6) 0.0123(6) -0.0003(5) -0.0007(5) -0.0018(5)
O2 0.0147(7) 0.0068(7) 0.0180(7) 0.0008(5) 0.0002(5) -0.0002(5)
O3 0.0201(7) 0.0066(7) 0.0105(6) -0.0003(5) -0.0011(5) -0.0014(5)
O4 0.0208(7) 0.0106(7) 0.0116(6) -0.0028(5) 0.0021(5) -0.0043(5)
O5 0.0143(7) 0.0108(7) 0.0125(7) 0.0003(5) 0.0018(5) 0.0004(5)
N1 0.0099(7) 0.0083(8) 0.0116(7) -0.0017(6) -0.0007(6) -0.0005(6)
N2 0.0135(8) 0.0075(8) 0.0107(7) -0.0005(6) -0.0013(6) -0.0013(6)
N3 0.0126(8) 0.0103(8) 0.0095(7) -0.0007(6) 0.0007(6) -0.0024(6)
N4 0.0183(9) 0.0084(8) 0.0109(7) -0.0025(6) 0.0016(6) -0.0028(6)
N5 0.0105(8) 0.0096(8) 0.0098(7) 0.0006(6) 0.0001(6) -0.0021(6)
C1 0.0129(9) 0.0117(10) 0.0123(9) -0.0025(7) -0.0018(7) 0.0006(7)
C2 0.0148(9) 0.0116(9) 0.0109(8) -0.0005(7) -0.0022(7) 0.0006(7)
C3 0.0096(9) 0.0075(9) 0.0106(8) -0.0010(7) 0.0011(6) 0.0003(7)
C4 0.0203(10) 0.0117(10) 0.0124(9) 0.0003(7) 0.0025(7) -0.0044(8)
C5 0.0239(11) 0.0142(10) 0.0107(9) 0.0005(7) 0.0039(7) -0.0043(8)
C6 0.0107(9) 0.0097(9) 0.0102(8) -0.0018(7) 0.0000(6) -0.0012(7)
C7 0.0087(9) 0.0076(9) 0.0120(8) -0.0017(7) -0.0001(6) -0.0011(7)
C8 0.0136(9) 0.0138(10) 0.0113(8) -0.0024(7) -0.0034(7) -0.0019(7)
C9 0.0158(10) 0.0221(11) 0.0244(11) 0.0023(8) -0.0049(8) -0.0074(8)
C10 0.0199(10) 0.0178(11) 0.0157(9) 0.0030(8) -0.0049(8) -0.0013(8)
C11 0.0084(8) 0.0122(10) 0.0118(8) -0.0003(7) 0.0024(6) -0.0039(7)
C12 0.0097(9) 0.0100(9) 0.0123(8) -0.0008(7) 0.0029(6) -0.0023(7)
Cl1 0.0099(2) 0.0167(2) 0.0144(2) -0.00292(17) -0.00054(16) 0.00036(17)
O6 0.0160(8) 0.0190(8) 0.0380(9) 0.0010(7) 0.0008(6) -0.0048(6)
O7 0.0162(7) 0.0196(8) 0.0235(7) -0.0104(6) 0.0035(6) -0.0028(6)
O8 0.0085(7) 0.0227(8) 0.0429(9) 0.0045(7) -0.0004(6) -0.0029(6)
O9 0.0373(10) 0.0329(10) 0.0144(7) -0.0039(7) -0.0048(6) 0.0125(8)
O10 0.0268(9) 0.0242(9) 0.0152(7) 0.0043(6) -0.0040(6) -0.0016(7)
O11 0.0231(8) 0.0123(8) 0.0253(8) -0.0008(6) -0.0057(7) 0.0005(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 1.9543(13) . ?
Cu1 O3 1.9571(13) . ?
Cu1 N3 1.9665(15) . ?
Cu1 N1 1.9812(16) . ?
O1 C11 1.282(2) . ?
O2 C11 1.228(2) . ?
O3 C12 1.283(2) . ?
O4 C12 1.233(2) . ?
O5 H05A 0.817(9) . ?
O5 H05B 0.817(9) . ?
N1 C3 1.333(2) . ?
N1 C1 1.381(2) . ?
N2 C3 1.340(2) . ?
N2 C2 1.371(2) . ?
N2 H2N 0.86(3) . ?
N3 C6 1.329(2) . ?
N3 C4 1.374(2) . ?
N4 C6 1.348(2) . ?
N4 C5 1.372(2) . ?
N4 H4N 0.82(2) . ?
N5 C8 1.516(2) . ?
N5 C7 1.519(2) . ?
N5 H5A 0.94(3) . ?
N5 H5B 0.86(3) . ?
C1 C2 1.356(3) . ?
C1 H1 0.9500 . ?
C2 H2 0.9500 . ?
C3 C7 1.501(2) . ?
C4 C5 1.360(3) . ?
C4 H4 0.9500 . ?
C5 H5 0.9500 . ?
C6 C7 1.487(2) . ?
C7 H7 1.0000 . ?
C8 C10 1.517(3) . ?
C8 C9 1.521(3) . ?
C8 H8 1.0000 . ?
C9 H9A 0.9800 . ?
C9 H9B 0.9800 . ?
C9 H9C 0.9800 . ?
C10 H10A 0.9800 . ?
C10 H10B 0.9800 . ?
C10 H10C 0.9800 . ?
C11 C12 1.555(3) . ?
Cl1 O7 1.4389(14) . ?
Cl1 O9 1.4394(15) . ?
Cl1 O8 1.4425(15) . ?
Cl1 O6 1.4485(16) . ?
O10 H00A 0.815(10) . ?
O10 H00B 0.817(9) . ?
O11 H01A 0.814(9) . ?
O11 H01B 0.818(10) . ?

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 O3 84.68(5) . . ?
O1 Cu1 N3 94.45(6) . . ?
O3 Cu1 N3 174.41(6) . . ?
O1 Cu1 N1 174.75(6) . . ?
O3 Cu1 N1 91.99(6) . . ?
N3 Cu1 N1 89.25(6) . . ?
C11 O1 Cu1 112.76(12) . . ?
C12 O3 Cu1 112.49(11) . . ?
H05A O5 H05B 109.4(15) . . ?
C3 N1 C1 106.16(15) . . ?
C3 N1 Cu1 122.91(12) . . ?
C1 N1 Cu1 128.36(12) . . ?
C3 N2 C2 108.00(16) . . ?
C3 N2 H2N 125.9(18) . . ?
C2 N2 H2N 125.8(18) . . ?
C6 N3 C4 106.47(15) . . ?
C6 N3 Cu1 123.91(12) . . ?
C4 N3 Cu1 128.71(13) . . ?
C6 N4 C5 107.82(16) . . ?
C6 N4 H4N 123.3(17) . . ?
C5 N4 H4N 128.9(16) . . ?
C8 N5 C7 116.24(14) . . ?
C8 N5 H5A 110.4(15) . . ?
C7 N5 H5A 106.3(15) . . ?
C8 N5 H5B 111.0(16) . . ?
C7 N5 H5B 104.8(16) . . ?
H5A N5 H5B 108(2) . . ?
C2 C1 N1 108.97(16) . . ?
C2 C1 H1 125.5 . . ?
N1 C1 H1 125.5 . . ?
C1 C2 N2 106.51(16) . . ?
C1 C2 H2 126.7 . . ?
N2 C2 H2 126.7 . . ?
N1 C3 N2 110.36(16) . . ?
N1 C3 C7 125.31(16) . . ?
N2 C3 C7 124.32(16) . . ?
C5 C4 N3 109.22(17) . . ?
C5 C4 H4 125.4 . . ?
N3 C4 H4 125.4 . . ?
C4 C5 N4 106.23(17) . . ?
C4 C5 H5 126.9 . . ?
N4 C5 H5 126.9 . . ?
N3 C6 N4 110.26(16) . . ?
N3 C6 C7 125.83(15) . . ?
N4 C6 C7 123.87(16) . . ?
C6 C7 C3 111.54(15) . . ?
C6 C7 N5 111.19(15) . . ?
C3 C7 N5 109.22(14) . . ?
C6 C7 H7 108.3 . . ?
C3 C7 H7 108.3 . . ?
N5 C7 H7 108.3 . . ?
N5 C8 C10 110.52(15) . . ?
N5 C8 C9 107.87(15) . . ?
C10 C8 C9 111.67(16) . . ?
N5 C8 H8 108.9 . . ?
C10 C8 H8 108.9 . . ?
C9 C8 H8 108.9 . . ?
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 . . ?
C8 C10 H10A 109.5 . . ?
C8 C10 H10B 109.5 . . ?
H10A C10 H10B 109.5 . . ?
C8 C10 H10C 109.5 . . ?
H10A C10 H10C 109.5 . . ?
H10B C10 H10C 109.5 . . ?
O2 C11 O1 126.25(17) . . ?
O2 C11 C12 119.01(15) . . ?
O1 C11 C12 114.74(15) . . ?
O4 C12 O3 125.83(17) . . ?
O4 C12 C11 119.40(16) . . ?
O3 C12 C11 114.77(15) . . ?
O7 Cl1 O9 109.36(9) . . ?
O7 Cl1 O8 110.18(9) . . ?
O9 Cl1 O8 110.28(10) . . ?
O7 Cl1 O6 110.21(9) . . ?
O9 Cl1 O6 109.05(10) . . ?
O8 Cl1 O6 107.74(9) . . ?
H00A O10 H00B 110.3(16) . . ?
H01A O11 H01B 109.4(16) . . ?

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
O3 Cu1 O1 C11 -0.05(12) . . . . ?
N3 Cu1 O1 C11 174.40(12) . . . . ?
N1 Cu1 O1 C11 -50.8(6) . . . . ?
O1 Cu1 O3 C12 4.81(12) . . . . ?
N3 Cu1 O3 C12 -76.5(6) . . . . ?
N1 Cu1 O3 C12 -179.26(13) . . . . ?
O1 Cu1 N1 C3 -96.7(6) . . . . ?
O3 Cu1 N1 C3 -147.21(14) . . . . ?
N3 Cu1 N1 C3 38.24(14) . . . . ?
O1 Cu1 N1 C1 62.6(7) . . . . ?
O3 Cu1 N1 C1 12.04(16) . . . . ?
N3 Cu1 N1 C1 -162.51(16) . . . . ?
O1 Cu1 N3 C6 153.23(15) . . . . ?
O3 Cu1 N3 C6 -126.0(6) . . . . ?
N1 Cu1 N3 C6 -23.04(15) . . . . ?
O1 Cu1 N3 C4 -39.19(17) . . . . ?
O3 Cu1 N3 C4 41.6(7) . . . . ?
N1 Cu1 N3 C4 144.53(17) . . . . ?
C3 N1 C1 C2 0.8(2) . . . . ?
Cu1 N1 C1 C2 -161.18(13) . . . . ?
N1 C1 C2 N2 -0.5(2) . . . . ?
C3 N2 C2 C1 0.0(2) . . . . ?
C1 N1 C3 N2 -0.8(2) . . . . ?
Cu1 N1 C3 N2 162.39(12) . . . . ?
C1 N1 C3 C7 178.01(16) . . . . ?
Cu1 N1 C3 C7 -18.8(2) . . . . ?
C2 N2 C3 N1 0.5(2) . . . . ?
C2 N2 C3 C7 -178.30(16) . . . . ?
C6 N3 C4 C5 0.4(2) . . . . ?
Cu1 N3 C4 C5 -168.88(14) . . . . ?
N3 C4 C5 N4 0.1(2) . . . . ?
C6 N4 C5 C4 -0.5(2) . . . . ?
C4 N3 C6 N4 -0.7(2) . . . . ?
Cu1 N3 C6 N4 169.20(12) . . . . ?
C4 N3 C6 C7 176.91(17) . . . . ?
Cu1 N3 C6 C7 -13.2(3) . . . . ?
C5 N4 C6 N3 0.8(2) . . . . ?
C5 N4 C6 C7 -176.91(17) . . . . ?
N3 C6 C7 C3 43.1(2) . . . . ?
N4 C6 C7 C3 -139.56(18) . . . . ?
N3 C6 C7 N5 -79.1(2) . . . . ?
N4 C6 C7 N5 98.3(2) . . . . ?
N1 C3 C7 C6 -25.2(2) . . . . ?
N2 C3 C7 C6 153.47(17) . . . . ?
N1 C3 C7 N5 98.1(2) . . . . ?
N2 C3 C7 N5 -83.2(2) . . . . ?
C8 N5 C7 C6 -60.9(2) . . . . ?
C8 N5 C7 C3 175.63(15) . . . . ?
C7 N5 C8 C10 92.46(19) . . . . ?
C7 N5 C8 C9 -145.20(16) . . . . ?
Cu1 O1 C11 O2 175.51(15) . . . . ?
Cu1 O1 C11 C12 -3.95(18) . . . . ?
Cu1 O3 C12 O4 172.74(15) . . . . ?
Cu1 O3 C12 C11 -7.90(18) . . . . ?
O2 C11 C12 O4 8.1(3) . . . . ?
O1 C11 C12 O4 -172.40(16) . . . . ?
O2 C11 C12 O3 -171.30(16) . . . . ?
O1 C11 C12 O3 8.2(2) . . . . ?

_diffrn_measured_fraction_theta_max 0.991
_diffrn_reflns_theta_full        27.48
_diffrn_measured_fraction_theta_full 0.991
_refine_diff_density_max         0.684
_refine_diff_density_min         -0.420
_refine_diff_density_rms         0.068

#===END