# Electronic Supplementary Material (ESI) for CrystEngComm
# This journal is © The Royal Society of Chemistry 2013


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#                                CCDC 
# 
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# 
#  This CIF contains data from an original supplementary publication 
#  deposited with the CCDC, and may include chemical, crystal,   
#  experimental, refinement, atomic coordinates, 
#  anisotropic displacement parameters and molecular geometry data,
#  as required by the journal to which it was submitted. 
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data_2
_database_code_depnum_ccdc_archive 'CCDC 906127'
#TrackingRef '17724_web_deposit_cif_file_1_YunLing_1360810150.906127.cif'
_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C10 H24 Cu3 N6 O8, C2 N H7'
_chemical_formula_sum            'C12 H31 Cu3 N7 O8'
_chemical_formula_weight         592.06
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'
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           Trigonal
_symmetry_space_group_name_H-M   R3m
_symmetry_space_group_name_Hall  'R 3 -2"'
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-y, x-y, z'
'-x+y, -x, z'
'-y, -x, z'
'x, x-y, z'
'-x+y, y, z'
'x+2/3, y+1/3, z+1/3'
'-y+2/3, x-y+1/3, z+1/3'
'-x+y+2/3, -x+1/3, z+1/3'
'-y+2/3, -x+1/3, z+1/3'
'x+2/3, x-y+1/3, z+1/3'
'-x+y+2/3, y+1/3, z+1/3'
'x+1/3, y+2/3, z+2/3'
'-y+1/3, x-y+2/3, z+2/3'
'-x+y+1/3, -x+2/3, z+2/3'
'-y+1/3, -x+2/3, z+2/3'
'x+1/3, x-y+2/3, z+2/3'
'-x+y+1/3, y+2/3, z+2/3'
_cell_length_a                   24.401(4)
_cell_length_b                   24.401(4)
_cell_length_c                   11.5733(18)
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                120.00
_cell_volume                     5967.6(17)
_cell_formula_units_Z            9
_cell_measurement_temperature    173(2)
_cell_measurement_reflns_used    4914
_cell_measurement_theta_min      2.61
_cell_measurement_theta_max      25.98
_exptl_crystal_description       block
_exptl_crystal_colour            blue
_exptl_crystal_size_max          0.20
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.15
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.483
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             2727
_exptl_absorpt_coefficient_mu    2.427
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.6424
_exptl_absorpt_correction_T_max  0.7122
_exptl_absorpt_process_details   SADABS
_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  'Bruker APEX-II CCD'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            11895
_diffrn_reflns_av_R_equivalents  0.0346
_diffrn_reflns_av_sigmaI/netI    0.0366
_diffrn_reflns_limit_h_min       -29
_diffrn_reflns_limit_h_max       29
_diffrn_reflns_limit_k_min       -26
_diffrn_reflns_limit_k_max       29
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_theta_min         1.67
_diffrn_reflns_theta_max         25.19
_reflns_number_total             2542
_reflns_number_gt                2322
_reflns_threshold_expression     >2sigma(I)
_computing_data_collection       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_refine_special_details          
;
Refinement of F^2^ against ALL reflections. The weighted R-factor wR and
goodness of fit S are based on F^2^, conventional R-factors R are based
on F, with F set to zero for negative F^2^. The threshold expression of
F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is
not relevant to the choice of reflections for refinement. R-factors based
on F^2^ are statistically about twice as large as those based on F, and R-
factors based on ALL data will be even larger.
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[\s^2^(Fo^2^)+(0.1007P)^2^+20.0944P] 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   0.02(4)
_refine_ls_number_reflns         2542
_refine_ls_number_parameters     159
_refine_ls_number_restraints     28
_refine_ls_R_factor_all          0.0615
_refine_ls_R_factor_gt           0.0555
_refine_ls_wR_factor_ref         0.1568
_refine_ls_wR_factor_gt          0.1499
_refine_ls_goodness_of_fit_ref   1.132
_refine_ls_restrained_S_all      1.130
_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 0.06354(7) 0.53177(4) 0.61591(11) 0.0470(4) Uani 1 2 d S . .
Cu2 Cu 0.02826(4) 0.57320(4) 0.37064(5) 0.0424(3) Uani 1 1 d . . .
O1 O 0.0757(3) 0.53785(17) 0.4486(6) 0.0393(14) Uani 1 2 d S . .
H1 H 0.1134 0.5567 0.4238 0.047 Uiso 1 2 d SR . .
O2 O 0.0116(4) 0.5058(2) 0.2647(6) 0.0458(17) Uani 1 2 d S . .
O3 O 0.0233(6) 0.5116(3) 0.7705(9) 0.077(3) Uani 1 2 d S . .
O4 O -0.0691(11) 0.4654(5) 0.699(2) 0.202(12) Uani 1 2 d S . .
O5 O -0.0533(7) 0.4734(3) 0.4872(15) 0.111(4) Uani 1 2 d SU . .
H5D H -0.0534 0.4488 0.4328 0.133 Uiso 1 1 d R . .
O6 O 0.1658(6) 0.5829(3) 0.6750(11) 0.097(4) Uani 1 2 d S . .
H6A H 0.1890 0.6221 0.6566 0.117 Uiso 1 1 d R . .
O7 O 0.1271(5) 0.6545(6) 0.2856(10) 0.129(4) Uani 1 1 d . . .
H7A H 0.1519 0.6388 0.2979 0.155 Uiso 1 1 d R . .
H7B H 0.1296 0.6661 0.2141 0.155 Uiso 1 1 d R . .
N1 N 0.0646(3) 0.6136(3) 0.6071(5) 0.0427(13) Uani 1 1 d . . .
N2 N 0.0501(3) 0.6310(3) 0.5040(5) 0.0412(13) Uani 1 1 d . . .
N3 N 0.0744(3) 0.7070(3) 0.6342(5) 0.0437(13) Uani 1 1 d . . .
N4 N 0.2793(7) 0.4957(9) 0.5558(17) 0.198(19) Uani 0.50 1 d PDU . .
C1 C 0.0974(6) 0.6585(5) 0.8042(7) 0.068(3) Uani 1 1 d . . .
H1A H 0.1010 0.6208 0.8187 0.102 Uiso 1 1 calc R . .
H1B H 0.0656 0.6584 0.8561 0.102 Uiso 1 1 calc R . .
H1C H 0.1384 0.6966 0.8180 0.102 Uiso 1 1 calc R . .
C2 C 0.0779(4) 0.6580(3) 0.6818(6) 0.0438(16) Uani 1 1 d . . .
C3 C 0.0573(4) 0.6880(4) 0.5227(6) 0.0435(16) Uani 1 1 d . . .
C4 C 0.0482(5) 0.7268(4) 0.4327(7) 0.058(2) Uani 1 1 d . . .
H4A H 0.0119 0.7317 0.4537 0.087 Uiso 1 1 calc R . .
H4B H 0.0403 0.7055 0.3577 0.087 Uiso 1 1 calc R . .
H4C H 0.0863 0.7686 0.4279 0.087 Uiso 1 1 calc R . .
C5 C -0.0613(15) 0.4693(8) 0.900(3) 0.169(14) Uani 1 2 d S . .
H5A H -0.0292 0.4854 0.9587 0.253 Uiso 1 2 d SR . .
H5B H -0.0869 0.4887 0.9085 0.253 Uiso 0.50 1 d PR . .
H5C H -0.0874 0.4242 0.9081 0.253 Uiso 0.50 1 d PR . .
C6 C -0.0301(12) 0.4849(6) 0.776(2) 0.122(7) Uani 1 2 d S . .
C7 C 0.2480(7) 0.4961(13) 0.6736(15) 0.193(17) Uani 1 2 d SDU . .
C8 C 0.2219(4) 0.4439(8) 0.4858(15) 0.147(11) Uani 1 2 d SDU . .
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 0.0741(9) 0.0460(5) 0.0301(6) -0.0032(3) -0.0063(6) 0.0370(5)
Cu2 0.0583(5) 0.0479(5) 0.0308(4) -0.0092(3) -0.0122(4) 0.0340(4)
O1 0.049(4) 0.039(2) 0.033(3) -0.0024(14) -0.005(3) 0.0243(19)
O2 0.071(5) 0.044(2) 0.031(3) -0.0090(16) -0.018(3) 0.036(2)
O3 0.112(9) 0.075(4) 0.055(5) 0.006(3) 0.011(6) 0.056(5)
O4 0.143(17) 0.25(2) 0.18(2) -0.025(9) -0.051(17) 0.071(9)
O5 0.105(7) 0.104(6) 0.124(8) 0.005(3) 0.009(6) 0.052(3)
O6 0.093(8) 0.092(5) 0.107(8) -0.027(3) -0.053(7) 0.046(4)
O7 0.129(8) 0.144(9) 0.116(8) 0.036(7) 0.049(7) 0.071(7)
N1 0.065(4) 0.040(3) 0.029(3) 0.000(2) -0.006(3) 0.031(3)
N2 0.060(3) 0.039(3) 0.029(3) -0.001(2) -0.004(2) 0.029(3)
N3 0.058(4) 0.047(3) 0.027(3) -0.005(2) 0.002(3) 0.026(3)
N4 0.31(4) 0.16(2) 0.22(3) -0.14(2) -0.20(3) 0.19(3)
C1 0.118(8) 0.066(5) 0.040(4) -0.008(4) -0.018(5) 0.061(6)
C2 0.061(4) 0.043(3) 0.027(3) 0.003(3) 0.004(3) 0.026(3)
C3 0.057(4) 0.048(4) 0.026(3) 0.001(3) 0.002(3) 0.027(3)
C4 0.088(6) 0.048(4) 0.041(4) -0.010(3) -0.013(4) 0.035(4)
C5 0.15(2) 0.22(3) 0.11(2) 0.000(9) 0.001(18) 0.076(12)
C6 0.096(16) 0.136(15) 0.120(19) -0.003(7) -0.006(15) 0.048(8)
C7 0.31(4) 0.14(2) 0.066(13) 0.019(15) 0.009(7) 0.072(12)
C8 0.22(3) 0.082(12) 0.088(14) 0.038(11) 0.019(6) 0.041(6)
_geom_special_details            
;
All esds (except the esd in the dihedral angle between two l.s. planes)
are estimated using the full covariance matrix. The cell esds are taken
into account individually in the estimation of esds in distances, angles
and torsion angles; correlations between esds in cell parameters are only
used when they are defined by crystal symmetry. An approximate (isotropic)
treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Cu1 O1 1.953(7) . ?
Cu1 O3 1.981(10) . ?
Cu1 N1 1.986(6) 5_565 ?
Cu1 N1 1.986(6) . ?
Cu1 O6 2.267(11) . ?
Cu2 O2 1.924(5) . ?
Cu2 N3 1.972(6) 15_454 ?
Cu2 O1 1.974(5) . ?
Cu2 N2 1.976(6) . ?
Cu2 O7 2.437(11) . ?
Cu2 O5 2.620(13) . ?
Cu2 Cu2 2.8828(17) 5_565 ?
O1 Cu2 1.974(5) 5_565 ?
O1 H1 0.8478 . ?
O2 Cu2 1.924(5) 5_565 ?
O3 C6 1.13(2) . ?
O4 C6 1.21(3) . ?
O5 H5D 0.8679 . ?
O6 H6A 0.8604 . ?
O7 H7A 0.8747 . ?
O7 H7B 0.8667 . ?
N1 C2 1.295(9) . ?
N1 N2 1.372(8) . ?
N2 C3 1.329(10) . ?
N3 C2 1.357(9) . ?
N3 C3 1.365(9) . ?
N3 Cu2 1.972(6) 8_565 ?
N4 N4 1.54(4) 6 ?
N4 C8 1.564(10) . ?
N4 C7 1.565(10) . ?
C1 C2 1.492(10) . ?
C1 H1A 0.9800 . ?
C1 H1B 0.9800 . ?
C1 H1C 0.9800 . ?
C3 C4 1.497(11) . ?
C4 H4A 0.9800 . ?
C4 H4B 0.9800 . ?
C4 H4C 0.9800 . ?
C5 C6 1.58(4) . ?
C5 H5A 0.9599 . ?
C5 H5B 0.9585 . ?
C5 H5C 0.9615 . ?
C7 N4 1.565(10) 6 ?
C8 N4 1.564(10) 6 ?
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 162.1(4) . . ?
O1 Cu1 N1 87.01(17) . 5_565 ?
O3 Cu1 N1 92.92(18) . 5_565 ?
O1 Cu1 N1 87.01(17) . . ?
O3 Cu1 N1 92.92(18) . . ?
N1 Cu1 N1 174.0(4) 5_565 . ?
O1 Cu1 O6 100.0(4) . . ?
O3 Cu1 O6 97.9(5) . . ?
N1 Cu1 O6 90.28(19) 5_565 . ?
N1 Cu1 O6 90.28(19) . . ?
O2 Cu2 N3 94.7(2) . 15_454 ?
O2 Cu2 O1 80.6(2) . . ?
N3 Cu2 O1 168.6(3) 15_454 . ?
O2 Cu2 N2 166.9(2) . . ?
N3 Cu2 N2 96.7(2) 15_454 . ?
O1 Cu2 N2 87.0(2) . . ?
O2 Cu2 O7 97.9(4) . . ?
N3 Cu2 O7 102.1(3) 15_454 . ?
O1 Cu2 O7 89.0(3) . . ?
N2 Cu2 O7 86.0(4) . . ?
O2 Cu2 O5 78.2(4) . . ?
N3 Cu2 O5 96.5(3) 15_454 . ?
O1 Cu2 O5 72.4(3) . . ?
N2 Cu2 O5 94.0(4) . . ?
O7 Cu2 O5 161.3(4) . . ?
O2 Cu2 Cu2 41.50(15) . 5_565 ?
N3 Cu2 Cu2 128.41(19) 15_454 5_565 ?
O1 Cu2 Cu2 43.10(14) . 5_565 ?
N2 Cu2 Cu2 125.39(16) . 5_565 ?
O7 Cu2 Cu2 108.6(3) . 5_565 ?
O5 Cu2 Cu2 56.62(18) . 5_565 ?
Cu1 O1 Cu2 112.7(3) . . ?
Cu1 O1 Cu2 112.7(3) . 5_565 ?
Cu2 O1 Cu2 93.8(3) . 5_565 ?
Cu1 O1 H1 117.4 . . ?
Cu2 O1 H1 108.8 . . ?
Cu2 O1 H1 108.8 5_565 . ?
Cu2 O2 Cu2 97.0(3) . 5_565 ?
C6 O3 Cu1 118.5(17) . . ?
Cu2 O5 H5D 90.5 . . ?
Cu1 O6 H6A 117.9 . . ?
Cu2 O7 H7A 101.4 . . ?
Cu2 O7 H7B 122.1 . . ?
H7A O7 H7B 110.3 . . ?
C2 N1 N2 108.4(6) . . ?
C2 N1 Cu1 132.8(5) . . ?
N2 N1 Cu1 118.7(4) . . ?
C3 N2 N1 105.3(6) . . ?
C3 N2 Cu2 136.2(5) . . ?
N1 N2 Cu2 118.5(4) . . ?
C2 N3 C3 103.2(6) . . ?
C2 N3 Cu2 129.3(5) . 8_565 ?
C3 N3 Cu2 127.4(5) . 8_565 ?
N4 N4 C8 60.6(7) 6 . ?
N4 N4 C7 60.6(7) 6 . ?
C8 N4 C7 102.3(9) . . ?
C2 C1 H1A 109.5 . . ?
C2 C1 H1B 109.5 . . ?
H1A C1 H1B 109.5 . . ?
C2 C1 H1C 109.5 . . ?
H1A C1 H1C 109.5 . . ?
H1B C1 H1C 109.5 . . ?
N1 C2 N3 111.5(6) . . ?
N1 C2 C1 125.8(7) . . ?
N3 C2 C1 122.6(6) . . ?
N2 C3 N3 111.5(6) . . ?
N2 C3 C4 124.4(6) . . ?
N3 C3 C4 124.0(7) . . ?
C3 C4 H4A 109.5 . . ?
C3 C4 H4B 109.5 . . ?
H4A C4 H4B 109.5 . . ?
C3 C4 H4C 109.5 . . ?
H4A C4 H4C 109.5 . . ?
H4B C4 H4C 109.5 . . ?
C6 C5 H5A 110.3 . . ?
C6 C5 H5B 109.1 . . ?
H5A C5 H5B 109.2 . . ?
C6 C5 H5C 109.0 . . ?
H5A C5 H5C 109.8 . . ?
H5B C5 H5C 109.5 . . ?
O3 C6 O4 130(3) . . ?
O3 C6 C5 118(3) . . ?
O4 C6 C5 113(3) . . ?
N4 C7 N4 58.8(14) . 6 ?
N4 C8 N4 58.9(14) 6 . ?
_diffrn_measured_fraction_theta_max 0.999
_diffrn_reflns_theta_full        25.19
_diffrn_measured_fraction_theta_full 0.999
_refine_diff_density_max         0.818
_refine_diff_density_min         -0.621
_refine_diff_density_rms         0.182


data_1
_database_code_depnum_ccdc_archive 'CCDC 924386'
#TrackingRef '17723_web_deposit_cif_file_0_YunLing_1360810150.906126.cif'
_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C9 H22 Cu3 N6 O8, H2 O'
_chemical_formula_sum            'C9 H24 Cu3 N6 O9'
_chemical_formula_weight         550.96
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cu Cu 0.3201 1.2651 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
_symmetry_cell_setting           Trigonal
_symmetry_space_group_name_H-M   R3m
_symmetry_space_group_name_Hall  'R 3 -2"'
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-y, x-y, z'
'-x+y, -x, z'
'-y, -x, z'
'-x+y, y, z'
'x, x-y, z'
'x+2/3, y+1/3, z+1/3'
'-y+2/3, x-y+1/3, z+1/3'
'-x+y+2/3, -x+1/3, z+1/3'
'-y+2/3, -x+1/3, z+1/3'
'-x+y+2/3, y+1/3, z+1/3'
'x+2/3, x-y+1/3, z+1/3'
'x+1/3, y+2/3, z+2/3'
'-y+1/3, x-y+2/3, z+2/3'
'-x+y+1/3, -x+2/3, z+2/3'
'-y+1/3, -x+2/3, z+2/3'
'-x+y+1/3, y+2/3, z+2/3'
'x+1/3, x-y+2/3, z+2/3'
_cell_length_a                   24.9131(14)
_cell_length_b                   24.9131(14)
_cell_length_c                   10.8608(12)
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                120.00
_cell_volume                     5837.8(8)
_cell_formula_units_Z            9
_cell_measurement_temperature    173(2)
_cell_measurement_reflns_used    3047
_cell_measurement_theta_min      2.66
_cell_measurement_theta_max      24.99
_exptl_crystal_description       block
_exptl_crystal_colour            blue
_exptl_crystal_size_max          0.20
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.15
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.410
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             2511
_exptl_absorpt_coefficient_mu    2.477
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.6371
_exptl_absorpt_correction_T_max  0.7076
_exptl_absorpt_process_details   sadabs
_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  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            9662
_diffrn_reflns_av_R_equivalents  0.0444
_diffrn_reflns_av_sigmaI/netI    0.0406
_diffrn_reflns_limit_h_min       -25
_diffrn_reflns_limit_h_max       30
_diffrn_reflns_limit_k_min       -30
_diffrn_reflns_limit_k_max       30
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_theta_min         2.10
_diffrn_reflns_theta_max         25.50
_reflns_number_total             2564
_reflns_number_gt                2372
_reflns_threshold_expression     >2sigma(I)
_computing_data_collection       'Bruker SMART'
_computing_cell_refinement       'Bruker SMART'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_refine_special_details          
;
Refinement of F^2^ against ALL reflections. The weighted R-factor wR and
goodness of fit S are based on F^2^, conventional R-factors R are based
on F, with F set to zero for negative F^2^. The threshold expression of
F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is
not relevant to the choice of reflections for refinement. R-factors based
on F^2^ are statistically about twice as large as those based on F, and R-
factors based on ALL data will be even larger.
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[\s^2^(Fo^2^)+(0.1111P)^2^+60.0539P] 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   0.03(5)
_refine_ls_number_reflns         2564
_refine_ls_number_parameters     136
_refine_ls_number_restraints     7
_refine_ls_R_factor_all          0.0711
_refine_ls_R_factor_gt           0.0658
_refine_ls_wR_factor_ref         0.1902
_refine_ls_wR_factor_gt          0.1866
_refine_ls_goodness_of_fit_ref   1.154
_refine_ls_restrained_S_all      1.155
_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
O6 O 0.4692(7) 0.3513(8) 1.1057(12) 0.114(5) Uani 1 1 d . . .
Cu1 Cu 0.53150(4) 0.46850(4) 0.73309(13) 0.0285(4) Uani 1 2 d S . .
Cu2 Cu 0.45478(5) 0.43069(5) 0.99348(8) 0.0337(3) Uani 1 1 d . . .
O1 O 0.5375(2) 0.4625(2) 0.9130(8) 0.0265(17) Uani 1 2 d S . .
H11A H 0.5562 0.4438 0.9220 0.032 Uiso 1 2 d SR . .
O2 O 0.5048(2) 0.4952(2) 1.1121(9) 0.037(2) Uani 1 2 d S . .
C1 C 0.4217(5) 0.3414(4) 0.6678(8) 0.032(2) Uani 1 1 d . . .
C2 C 0.4400(5) 0.3404(5) 0.5412(9) 0.044(3) Uani 1 1 d . . .
H2A H 0.4762 0.3805 0.5208 0.066 Uiso 1 1 calc R . .
H2B H 0.4056 0.3324 0.4860 0.066 Uiso 1 1 calc R . .
H2C H 0.4504 0.3076 0.5315 0.066 Uiso 1 1 calc R . .
C3 C 0.3754(4) 0.3143(4) 0.8422(9) 0.0318(19) Uani 1 1 d . . .
C4 C 0.3309(5) 0.2777(5) 0.9449(10) 0.048(3) Uani 1 1 d . . .
H4A H 0.3421 0.3032 1.0195 0.072 Uiso 1 1 calc R . .
H4B H 0.3334 0.2403 0.9614 0.072 Uiso 1 1 calc R . .
H4C H 0.2886 0.2658 0.9203 0.072 Uiso 1 1 calc R . .
N1 N 0.4513(3) 0.3887(3) 0.7436(7) 0.0296(15) Uani 1 1 d . . .
N2 N 0.4211(3) 0.3717(4) 0.8579(7) 0.0313(17) Uani 1 1 d . . .
N3 N 0.3728(4) 0.2930(3) 0.7274(7) 0.0338(17) Uani 1 1 d . . .
O3 O 0.5822(3) 0.4178(3) 0.6737(11) 0.056(3) Uani 1 2 d S . .
H3A H 0.6189 0.4430 0.6627 0.085 Uiso 1 1 d R . .
O4 O 0.5128(3) 0.4872(3) 0.5687(10) 0.045(2) Uani 1 2 d S . .
O5 O 0.4644(5) 0.5356(5) 0.649(3) 0.198(17) Uani 1 2 d S . .
C5 C 0.4837(8) 0.5163(8) 0.559(2) 0.102(9) Uani 1 2 d S . .
H5A H 0.4752 0.5248 0.4784 0.123 Uiso 1 2 calc SR . .
H6A H 0.4626 0.3208 1.1505 0.153 Uiso 1 1 d R . .
H6B H 0.5060 0.3673 1.0779 0.153 Uiso 1 1 d R . .
O7 O 0.4730(3) 0.5270(3) 0.8684(16) 0.072(4) Uani 1 2 d SU . .
H7A H 0.4396 0.5061 0.8273 0.108 Uiso 1 1 d R . .
O8 O 0.4428(6) 0.5572(6) 0.220(3) 0.190(14) Uani 1 2 d S . .
H8A H 0.4041 0.5408 0.2027 0.285 Uiso 1 1 d R . .
loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_23
_atom_site_aniso_U_13
_atom_site_aniso_U_12
O6 0.119(10) 0.162(14) 0.074(7) 0.039(9) 0.019(7) 0.079(10)
Cu1 0.0295(6) 0.0295(6) 0.0219(7) -0.0019(3) 0.0019(3) 0.0113(7)
Cu2 0.0239(5) 0.0347(6) 0.0305(6) -0.0125(4) 0.0056(4) 0.0058(4)
O1 0.030(3) 0.030(3) 0.021(4) -0.0030(17) 0.0030(17) 0.016(4)
O2 0.033(4) 0.033(4) 0.043(5) -0.003(2) 0.003(2) 0.016(4)
C1 0.045(5) 0.034(5) 0.025(5) -0.004(4) -0.013(4) 0.027(4)
C2 0.061(7) 0.039(5) 0.020(4) -0.010(4) -0.007(4) 0.015(5)
C3 0.031(5) 0.025(4) 0.036(5) 0.001(4) 0.006(4) 0.011(4)
C4 0.050(6) 0.040(6) 0.042(6) 0.003(5) 0.023(5) 0.014(5)
N1 0.033(4) 0.030(4) 0.023(3) 0.000(3) -0.002(3) 0.013(3)
N2 0.019(3) 0.027(4) 0.036(4) -0.010(3) 0.003(3) 0.003(3)
N3 0.042(4) 0.029(4) 0.025(4) -0.009(3) -0.010(3) 0.014(3)
O3 0.057(5) 0.057(5) 0.066(7) -0.013(3) 0.013(3) 0.036(6)
O4 0.044(4) 0.044(4) 0.041(6) 0.005(3) -0.005(3) 0.016(5)
O5 0.33(4) 0.33(4) 0.11(2) -0.008(6) 0.008(6) 0.31(4)
C5 0.123(15) 0.123(15) 0.048(12) 0.012(8) -0.012(8) 0.051(19)
O7 0.062(5) 0.062(5) 0.103(8) 0.007(3) -0.007(3) 0.039(5)
O8 0.21(2) 0.21(2) 0.19(3) -0.056(11) 0.056(11) 0.14(3)
_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
O6 Cu2 2.499(15) . ?
O6 H6A 0.8466 . ?
O6 H6B 0.8515 . ?
Cu1 O4 1.960(10) . ?
Cu1 O1 1.971(8) . ?
Cu1 N1 1.997(7) . ?
Cu1 N1 1.997(7) 4_665 ?
Cu1 O3 2.279(10) . ?
Cu2 O2 1.948(7) . ?
Cu2 N2 1.949(7) . ?
Cu2 N3 1.981(7) 8 ?
Cu2 O1 2.001(6) . ?
Cu2 Cu2 2.853(2) 4_665 ?
O1 Cu2 2.001(6) 4_665 ?
O1 H11A 0.8119 . ?
O2 Cu2 1.948(7) 4_665 ?
C1 N1 1.319(11) . ?
C1 N3 1.374(13) . ?
C1 C2 1.452(13) . ?
C2 H2A 0.9800 . ?
C2 H2B 0.9800 . ?
C2 H2C 0.9800 . ?
C3 N2 1.319(12) . ?
C3 N3 1.344(12) . ?
C3 C4 1.514(13) . ?
C4 H4A 0.9800 . ?
C4 H4B 0.9800 . ?
C4 H4C 0.9800 . ?
N1 N2 1.402(11) . ?
N3 Cu2 1.981(7) 15_554 ?
O3 H3A 0.8196 . ?
O4 C5 1.26(3) . ?
O5 C5 1.28(4) . ?
C5 H5A 0.9500 . ?
O7 H7A 0.8543 . ?
O8 H8A 0.8595 . ?
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
Cu2 O6 H6A 162.0 . . ?
Cu2 O6 H6B 90.1 . . ?
H6A O6 H6B 107.9 . . ?
O4 Cu1 O1 163.2(4) . . ?
O4 Cu1 N1 92.9(2) . . ?
O1 Cu1 N1 86.8(2) . . ?
O4 Cu1 N1 92.9(2) . 4_665 ?
O1 Cu1 N1 86.8(2) . 4_665 ?
N1 Cu1 N1 173.4(4) . 4_665 ?
O4 Cu1 O3 97.9(5) . . ?
O1 Cu1 O3 98.9(4) . . ?
N1 Cu1 O3 91.1(2) . . ?
N1 Cu1 O3 91.1(2) 4_665 . ?
O2 Cu2 N2 168.1(3) . . ?
O2 Cu2 N3 95.7(3) . 8 ?
N2 Cu2 N3 96.0(3) . 8 ?
O2 Cu2 O1 81.6(3) . . ?
N2 Cu2 O1 86.5(3) . . ?
N3 Cu2 O1 169.4(3) 8 . ?
O2 Cu2 O6 92.5(5) . . ?
N2 Cu2 O6 87.1(5) . . ?
N3 Cu2 O6 100.4(4) 8 . ?
O1 Cu2 O6 90.0(4) . . ?
O2 Cu2 Cu2 42.9(2) . 4_665 ?
N2 Cu2 Cu2 126.3(2) . 4_665 ?
N3 Cu2 Cu2 128.4(2) 8 4_665 ?
O1 Cu2 Cu2 44.52(17) . 4_665 ?
O6 Cu2 Cu2 108.9(4) . 4_665 ?
Cu1 O1 Cu2 111.2(3) . 4_665 ?
Cu1 O1 Cu2 111.2(3) . . ?
Cu2 O1 Cu2 91.0(3) 4_665 . ?
Cu1 O1 H11A 104.4 . . ?
Cu2 O1 H11A 119.5 4_665 . ?
Cu2 O1 H11A 119.5 . . ?
Cu2 O2 Cu2 94.2(4) . 4_665 ?
N1 C1 N3 110.1(8) . . ?
N1 C1 C2 124.5(9) . . ?
N3 C1 C2 125.3(8) . . ?
C1 C2 H2A 109.5 . . ?
C1 C2 H2B 109.5 . . ?
H2A C2 H2B 109.5 . . ?
C1 C2 H2C 109.5 . . ?
H2A C2 H2C 109.5 . . ?
H2B C2 H2C 109.5 . . ?
N2 C3 N3 113.1(8) . . ?
N2 C3 C4 122.2(9) . . ?
N3 C3 C4 124.7(8) . . ?
C3 C4 H4A 109.5 . . ?
C3 C4 H4B 109.5 . . ?
H4A C4 H4B 109.5 . . ?
C3 C4 H4C 109.5 . . ?
H4A C4 H4C 109.5 . . ?
H4B C4 H4C 109.5 . . ?
C1 N1 N2 107.9(7) . . ?
C1 N1 Cu1 133.5(7) . . ?
N2 N1 Cu1 118.0(5) . . ?
C3 N2 N1 104.8(7) . . ?
C3 N2 Cu2 136.7(7) . . ?
N1 N2 Cu2 118.5(5) . . ?
C3 N3 C1 104.1(7) . . ?
C3 N3 Cu2 126.9(7) . 15_554 ?
C1 N3 Cu2 128.9(6) . 15_554 ?
Cu1 O3 H3A 109.6 . . ?
C5 O4 Cu1 119.0(14) . . ?
O4 C5 O5 126(2) . . ?
O4 C5 H5A 117.2 . . ?
O5 C5 H5A 117.2 . . ?
_diffrn_measured_fraction_theta_max 0.998
_diffrn_reflns_theta_full        25.50
_diffrn_measured_fraction_theta_full 0.998
_refine_diff_density_max         1.335
_refine_diff_density_min         -1.196
_refine_diff_density_rms         0.179