# Electronic Supplementary Material (ESI) for Dalton Transactions
# This journal is © The Royal Society of Chemistry 2012


data_general
_journal_name_full               'Dalton Trans.'
_journal_coden_cambridge         0222
#TrackingRef '- JPLangCIF (revised).CIF'

_audit_creation_date             2011-05-02
_audit_creation_method           'SHELXL 97'
_audit_update_record             ?

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

# PROCESSING SUMMARY (IUCr Office Use Only)

_journal_date_recd_electronic    ?
_journal_date_from_coeditor      ?
_journal_date_accepted           ?
_journal_coeditor_code           ?

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

# SUBMISSION DETAILS

_publ_contact_author_name        'Jian-Ping Lang'
_publ_contact_author_email       jplang@suda.edu.cn
_publ_contact_author_fax         86-512-65880089
_publ_contact_author_phone       86-512-65882865
_publ_contact_author_address     
;
College of Chemistry and Chemical Engineering, Materials Science
Soochow University, Suzhou 215123, Jiangsu,
P. R. China
;
_publ_requested_category         FM
_publ_requested_coeditor_name    ?
#==============================================================================
# TITLE AND AUTHOR LIST

_publ_section_title              
;
ENTER SECTION TITLE
;
_publ_section_title_footnote     
;
ENTER FOOTNOTE TO TITLE OF PAPER
;
loop_
_publ_author_name
_publ_author_footnote
_publ_author_address
'Li-Li Miao'
;
FIRST AUTHORS FOOTNOTES
;
;
FIRST AUTHORS ADDRESS
;
'Hong-Xi Li' '' ''
'Miao Yu' '' ''
'Wei Zhao' '' ''
'Wei-Jie Gong' '' ''
'Jun Gao' '' ''
'Zhi-Gang Ren' '' ''
'Hui-Fang Wang' '' ''
'Jian-Ping Lang' '' ''
_publ_section_synopsis           
;
ENTER SYNOPSIS
;

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

# TEXT

_publ_section_abstract           
;
ENTER ABSTRACT
;
_publ_section_comment            
;
ENTER TEXT
;
_publ_section_references         
;
ENTER OTHER REFERENCES
;
_publ_section_figure_captions    
;
ENTER FIGURE CAPTIONS
;
_publ_section_exptl_prep         
;
ENTER COMPOUND PREPARATION DETAILS
;
_publ_section_exptl_refinement   
;
ENTER SPECIAL DETAILS OF THE REFINEMENT
;

data_t
_database_code_depnum_ccdc_archive 'CCDC 852498'
#TrackingRef '- JPLangCIF (revised).CIF'

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C22 H16 Cu2 N12 O6, 2(C3 H7 N O)'
_chemical_formula_sum            'C28 H30 Cu2 N14 O8'
_chemical_formula_weight         817.76

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   'P 21/c'
_symmetry_space_group_name_Hall  '-P 2ybc'

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

_cell_length_a                   12.497(3)
_cell_length_b                   7.7247(15)
_cell_length_c                   17.883(4)
_cell_angle_alpha                90.00
_cell_angle_beta                 103.55(3)
_cell_angle_gamma                90.00
_cell_volume                     1678.3(6)
_cell_formula_units_Z            2
_cell_measurement_temperature    223(2)
_cell_measurement_reflns_used    4689
_cell_measurement_theta_min      3.1251
_cell_measurement_theta_max      27.5087

_exptl_crystal_description       Platelet
_exptl_crystal_colour            Green
_exptl_crystal_size_max          0.20
_exptl_crystal_size_mid          0.10
_exptl_crystal_size_min          0.10
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.618
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             836
_exptl_absorpt_coefficient_mu    1.339
_exptl_absorpt_correction_type   Multi-Scan
_exptl_absorpt_correction_T_min  0.7756
_exptl_absorpt_correction_T_max  0.8777
_exptl_absorpt_process_details   
'Jacobson, R. (1998) Private communication to Rigaku Company, Tokyo, Japan.'

_exptl_special_details           
;
?
;

_diffrn_ambient_temperature      223(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  'Rigaku MercuryCCD area detector'
_diffrn_measurement_method       \w
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         0
_diffrn_standards_interval_count 0
_diffrn_standards_interval_time  0
_diffrn_standards_decay_%        0
_diffrn_reflns_number            8747
_diffrn_reflns_av_R_equivalents  0.0528
_diffrn_reflns_av_sigmaI/netI    0.0615
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_theta_min         3.13
_diffrn_reflns_theta_max         25.00
_reflns_number_total             2950
_reflns_number_gt                2254
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'CrystalClear, Ver. 1.30 (Rigaku/MSC, 2001)'
_computing_cell_refinement       'CrystalClear, Ver. 1.30 (Rigaku/MSC, 2001)'
_computing_data_reduction        
'CrystalStructure, Ver. 3.60 (Rigaku/MSC, 2004)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    'ORTEPII (Johnson, 1976)'
_computing_publication_material  SHELXL97

_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^)+(0.0643P)^2^+1.6050P] 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         2950
_refine_ls_number_parameters     237
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0995
_refine_ls_R_factor_gt           0.0724
_refine_ls_wR_factor_ref         0.1605
_refine_ls_wR_factor_gt          0.1465
_refine_ls_goodness_of_fit_ref   1.156
_refine_ls_restrained_S_all      1.156
_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 0.58937(6) 0.79464(9) 0.03383(4) 0.0423(3) Uani 1 1 d . . .
N1 N 0.8008(4) 0.5793(6) 0.0002(3) 0.0489(12) Uani 1 1 d . . .
H1 H 0.8275 0.6532 -0.0273 0.059 Uiso 1 1 calc R . .
N2 N 0.7094(4) 0.6063(6) 0.0267(3) 0.0436(11) Uani 1 1 d . . .
N3 N 0.5471(4) 0.6008(6) 0.0912(2) 0.0402(11) Uani 1 1 d . . .
N4 N 0.4492(4) 0.8880(6) 0.0543(2) 0.0418(11) Uani 1 1 d . . .
N5 N 0.3901(4) 1.0373(6) 0.0401(3) 0.0476(12) Uani 1 1 d . . .
N6 N 0.7342(4) 0.9168(7) 0.1954(3) 0.0504(13) Uani 1 1 d . . .
N7 N 0.0538(4) 1.0261(8) 0.1658(3) 0.0582(14) Uani 1 1 d . . .
O1 O 0.7003(4) 0.7823(7) 0.2190(3) 0.0742(14) Uani 1 1 d . . .
O2 O 0.7884(4) 1.0244(6) 0.2408(3) 0.0716(14) Uani 1 1 d . . .
O3 O 0.7106(4) 0.9474(6) 0.1245(2) 0.0591(12) Uani 1 1 d . . .
O4 O 0.0736(3) 1.2129(6) 0.0720(2) 0.0572(11) Uani 1 1 d . . .
C1 C 0.8451(5) 0.4233(8) 0.0220(4) 0.0553(17) Uani 1 1 d . . .
H1A H 0.9085 0.3767 0.0099 0.066 Uiso 1 1 calc R . .
C2 C 0.7818(5) 0.3444(8) 0.0647(4) 0.0519(16) Uani 1 1 d . . .
H2 H 0.7928 0.2347 0.0880 0.062 Uiso 1 1 calc R . .
C3 C 0.6986(5) 0.4592(7) 0.0665(3) 0.0426(14) Uani 1 1 d . . .
C4 C 0.6067(5) 0.4552(7) 0.1035(3) 0.0440(14) Uani 1 1 d . . .
C5 C 0.5788(6) 0.3226(8) 0.1474(4) 0.0569(17) Uani 1 1 d . . .
H5 H 0.6201 0.2198 0.1553 0.068 Uiso 1 1 calc R . .
C6 C 0.4907(6) 0.3435(8) 0.1790(3) 0.0578(17) Uani 1 1 d . . .
H6 H 0.4715 0.2548 0.2094 0.069 Uiso 1 1 calc R . .
C7 C 0.4288(5) 0.4946(8) 0.1668(3) 0.0491(15) Uani 1 1 d . . .
H7 H 0.3676 0.5098 0.1883 0.059 Uiso 1 1 calc R . .
C8 C 0.4603(5) 0.6217(8) 0.1219(3) 0.0417(13) Uani 1 1 d . . .
C9 C 0.4071(5) 0.7903(8) 0.1030(3) 0.0442(14) Uani 1 1 d . . .
C10 C 0.3214(6) 0.8755(9) 0.1222(4) 0.067(2) Uani 1 1 d . . .
H10 H 0.2781 0.8382 0.1556 0.080 Uiso 1 1 calc R . .
C11 C 0.3130(6) 1.0266(10) 0.0821(4) 0.072(2) Uani 1 1 d . . .
H11 H 0.2603 1.1128 0.0833 0.087 Uiso 1 1 calc R . .
C12 C 0.0880(5) 1.1719(9) 0.1406(4) 0.0584(17) Uani 1 1 d . . .
H12 H 0.1262 1.2505 0.1775 0.070 Uiso 1 1 calc R . .
C13 C -0.0085(7) 0.8993(11) 0.1131(4) 0.087(3) Uani 1 1 d . . .
H13A H 0.0034 0.9177 0.0621 0.130 Uiso 1 1 calc R . .
H13B H -0.0863 0.9116 0.1116 0.130 Uiso 1 1 calc R . .
H13C H 0.0156 0.7837 0.1306 0.130 Uiso 1 1 calc R . .
C14 C 0.0766(7) 0.9831(11) 0.2466(4) 0.083(2) Uani 1 1 d . . .
H14A H 0.1267 1.0681 0.2758 0.124 Uiso 1 1 calc R . .
H14B H 0.1100 0.8692 0.2546 0.124 Uiso 1 1 calc R . .
H14C H 0.0085 0.9832 0.2638 0.124 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 0.0435(4) 0.0386(4) 0.0449(4) 0.0064(3) 0.0103(3) 0.0099(3)
N1 0.042(3) 0.048(3) 0.057(3) 0.003(2) 0.014(2) 0.008(2)
N2 0.044(3) 0.039(3) 0.047(3) -0.001(2) 0.010(2) 0.007(2)
N3 0.039(3) 0.044(3) 0.040(2) 0.003(2) 0.012(2) 0.007(2)
N4 0.047(3) 0.046(3) 0.034(2) 0.006(2) 0.012(2) 0.007(2)
N5 0.045(3) 0.045(3) 0.057(3) 0.009(2) 0.019(2) 0.020(2)
N6 0.043(3) 0.048(3) 0.059(3) 0.001(3) 0.008(3) 0.007(2)
N7 0.057(3) 0.069(4) 0.048(3) 0.001(3) 0.013(3) -0.003(3)
O1 0.087(4) 0.070(4) 0.061(3) 0.004(2) 0.008(3) -0.012(3)
O2 0.069(3) 0.069(3) 0.070(3) -0.014(3) 0.001(2) -0.013(3)
O3 0.072(3) 0.051(3) 0.051(3) 0.003(2) 0.008(2) -0.001(2)
O4 0.051(3) 0.063(3) 0.057(3) 0.010(2) 0.010(2) 0.008(2)
C1 0.046(4) 0.046(4) 0.072(4) -0.001(3) 0.011(3) 0.018(3)
C2 0.055(4) 0.037(4) 0.065(4) 0.007(3) 0.016(3) 0.009(3)
C3 0.048(3) 0.040(3) 0.040(3) -0.001(2) 0.008(3) 0.007(3)
C4 0.053(4) 0.037(3) 0.038(3) -0.001(2) 0.002(3) 0.007(3)
C5 0.067(4) 0.044(4) 0.062(4) 0.010(3) 0.020(3) 0.010(3)
C6 0.082(5) 0.040(4) 0.055(4) 0.016(3) 0.024(4) 0.006(3)
C7 0.055(4) 0.052(4) 0.045(3) 0.003(3) 0.021(3) -0.001(3)
C8 0.046(3) 0.042(3) 0.037(3) 0.002(2) 0.009(3) 0.001(3)
C9 0.046(3) 0.047(4) 0.040(3) 0.007(3) 0.012(3) 0.003(3)
C10 0.068(4) 0.072(5) 0.073(4) 0.028(4) 0.042(4) 0.033(4)
C11 0.069(5) 0.069(5) 0.096(5) 0.033(4) 0.056(4) 0.032(4)
C12 0.051(4) 0.064(5) 0.060(4) -0.004(3) 0.012(3) 0.010(3)
C13 0.095(6) 0.087(6) 0.077(5) -0.007(4) 0.019(5) -0.031(5)
C14 0.094(6) 0.100(7) 0.056(4) 0.011(4) 0.019(4) -0.010(5)

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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Cu1 N5 1.912(5) 3_675 ?
Cu1 N3 1.956(5) . ?
Cu1 N4 2.006(5) . ?
Cu1 N2 2.115(5) . ?
Cu1 O3 2.273(4) . ?
N1 C1 1.345(7) . ?
N1 N2 1.351(6) . ?
N1 H1 0.8700 . ?
N2 C3 1.363(7) . ?
N3 C8 1.336(7) . ?
N3 C4 1.339(7) . ?
N4 C9 1.349(7) . ?
N4 N5 1.361(6) . ?
N5 C11 1.356(8) . ?
N5 Cu1 1.912(5) 3_675 ?
N6 O1 1.233(6) . ?
N6 O2 1.246(6) . ?
N6 O3 1.256(6) . ?
N7 C12 1.321(8) . ?
N7 C14 1.446(8) . ?
N7 C13 1.452(9) . ?
O4 C12 1.238(7) . ?
C1 C2 1.366(9) . ?
C1 H1A 0.9400 . ?
C2 C3 1.372(8) . ?
C2 H2 0.9400 . ?
C3 C4 1.454(8) . ?
C4 C5 1.384(8) . ?
C5 C6 1.360(9) . ?
C5 H5 0.9400 . ?
C6 C7 1.389(8) . ?
C6 H6 0.9400 . ?
C7 C8 1.383(8) . ?
C7 H7 0.9400 . ?
C8 C9 1.465(8) . ?
C9 C10 1.368(8) . ?
C10 C11 1.362(9) . ?
C10 H10 0.9400 . ?
C11 H11 0.9400 . ?
C12 H12 0.9400 . ?
C13 H13A 0.9700 . ?
C13 H13B 0.9700 . ?
C13 H13C 0.9700 . ?
C14 H14A 0.9700 . ?
C14 H14B 0.9700 . ?
C14 H14C 0.9700 . ?

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 N3 168.06(19) 3_675 . ?
N5 Cu1 N4 98.43(18) 3_675 . ?
N3 Cu1 N4 79.89(19) . . ?
N5 Cu1 N2 102.33(19) 3_675 . ?
N3 Cu1 N2 77.73(19) . . ?
N4 Cu1 N2 156.98(19) . . ?
N5 Cu1 O3 88.04(19) 3_675 . ?
N3 Cu1 O3 103.90(17) . . ?
N4 Cu1 O3 98.53(18) . . ?
N2 Cu1 O3 92.06(17) . . ?
C1 N1 N2 111.2(5) . . ?
C1 N1 H1 124.4 . . ?
N2 N1 H1 124.4 . . ?
N1 N2 C3 104.5(4) . . ?
N1 N2 Cu1 142.8(4) . . ?
C3 N2 Cu1 112.6(4) . . ?
C8 N3 C4 120.6(5) . . ?
C8 N3 Cu1 117.9(4) . . ?
C4 N3 Cu1 121.4(4) . . ?
C9 N4 N5 108.6(5) . . ?
C9 N4 Cu1 114.0(4) . . ?
N5 N4 Cu1 136.8(4) . . ?
C11 N5 N4 105.6(5) . . ?
C11 N5 Cu1 130.7(4) . 3_675 ?
N4 N5 Cu1 123.4(4) . 3_675 ?
O1 N6 O2 121.1(5) . . ?
O1 N6 O3 119.1(5) . . ?
O2 N6 O3 119.7(6) . . ?
C12 N7 C14 122.2(6) . . ?
C12 N7 C13 121.5(6) . . ?
C14 N7 C13 116.3(6) . . ?
N6 O3 Cu1 125.6(4) . . ?
N1 C1 C2 108.0(6) . . ?
N1 C1 H1A 126.0 . . ?
C2 C1 H1A 126.0 . . ?
C1 C2 C3 105.4(5) . . ?
C1 C2 H2 127.3 . . ?
C3 C2 H2 127.3 . . ?
N2 C3 C2 111.0(5) . . ?
N2 C3 C4 116.1(5) . . ?
C2 C3 C4 132.8(6) . . ?
N3 C4 C5 120.7(6) . . ?
N3 C4 C3 112.1(5) . . ?
C5 C4 C3 127.2(5) . . ?
C6 C5 C4 118.9(6) . . ?
C6 C5 H5 120.5 . . ?
C4 C5 H5 120.5 . . ?
C5 C6 C7 120.7(6) . . ?
C5 C6 H6 119.7 . . ?
C7 C6 H6 119.7 . . ?
C8 C7 C6 117.6(6) . . ?
C8 C7 H7 121.2 . . ?
C6 C7 H7 121.2 . . ?
N3 C8 C7 121.5(5) . . ?
N3 C8 C9 112.4(5) . . ?
C7 C8 C9 126.1(5) . . ?
N4 C9 C10 109.9(5) . . ?
N4 C9 C8 114.9(5) . . ?
C10 C9 C8 135.2(6) . . ?
C11 C10 C9 104.4(6) . . ?
C11 C10 H10 127.8 . . ?
C9 C10 H10 127.8 . . ?
N5 C11 C10 111.5(6) . . ?
N5 C11 H11 124.2 . . ?
C10 C11 H11 124.2 . . ?
O4 C12 N7 124.9(6) . . ?
O4 C12 H12 117.6 . . ?
N7 C12 H12 117.6 . . ?
N7 C13 H13A 109.5 . . ?
N7 C13 H13B 109.5 . . ?
H13A C13 H13B 109.5 . . ?
N7 C13 H13C 109.5 . . ?
H13A C13 H13C 109.5 . . ?
H13B C13 H13C 109.5 . . ?
N7 C14 H14A 109.5 . . ?
N7 C14 H14B 109.5 . . ?
H14A C14 H14B 109.5 . . ?
N7 C14 H14C 109.5 . . ?
H14A C14 H14C 109.5 . . ?
H14B C14 H14C 109.5 . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
N1 H1 O4 0.87 1.92 2.767(7) 163.2 3_675
C1 H1A O4 0.94 2.45 3.224(7) 139.2 1_645
C2 H2 O3 0.94 2.59 3.432(8) 149.0 1_545
C5 H5 O3 0.94 2.51 3.406(8) 159.3 1_545
C7 H7 O2 0.94 2.57 3.500(8) 173.1 2_645
C11 H11 O4 0.94 2.42 3.286(8) 153.0 .
C12 H12 O1 0.94 2.51 3.304(8) 142.1 2_655
C13 H13A O4 0.97 2.43 2.796(9) 101.6 .
C13 H13A O4 0.97 2.57 3.334(9) 135.5 3_575

_diffrn_measured_fraction_theta_max 0.997
_diffrn_reflns_theta_full        25.00
_diffrn_measured_fraction_theta_full 0.997
_refine_diff_density_max         1.188
_refine_diff_density_min         -0.415
_refine_diff_density_rms         0.081

#===END