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

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#
#                 Cambridge Crystallographic Data Centre
#                                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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#  fide research purposes only. It may contain copyright material
#  of the CCDC or of third parties, and may not be copied or further
#  disseminated in any form, whether machine-readable or not,
#  except for the purpose of generating routine backup copies
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#  data retrieval see:
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#  from this site to visualise CIF-encoded structures and 
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data_1

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C8 H16.80 Cu2 N4 O7.40'
_chemical_formula_weight         414.53

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 '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 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cu Cu -1.9646 0.5888 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_symmetry_cell_setting           Monoclinic
_symmetry_space_group_name_H-M   P21/m

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

_cell_length_a                   10.7521(8)
_cell_length_b                   11.7077(7)
_cell_length_c                   12.3439(10)
_cell_angle_alpha                90.00
_cell_angle_beta                 92.146(7)
_cell_angle_gamma                90.00
_cell_volume                     1552.79(19)
_cell_formula_units_Z            4
_cell_measurement_temperature    150(2)
_cell_measurement_reflns_used    ?
_cell_measurement_theta_min      ?
_cell_measurement_theta_max      ?

_exptl_crystal_description       ?
_exptl_crystal_colour            ?
_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    1.773
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             840
_exptl_absorpt_coefficient_mu    3.764
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.5198
_exptl_absorpt_correction_T_max  0.7047
_exptl_absorpt_process_details   ?

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      150(2)
_diffrn_radiation_wavelength     1.54178
_diffrn_radiation_type           CuK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  ?
_diffrn_measurement_method       ?
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            5587
_diffrn_reflns_av_R_equivalents  0.0258
_diffrn_reflns_av_sigmaI/netI    0.0321
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_theta_min         3.58
_diffrn_reflns_theta_max         60.84
_reflns_number_total             2454
_reflns_number_gt                2182
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_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^)+(0.1183P)^2^+43.7783P] 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         2454
_refine_ls_number_parameters     226
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1011
_refine_ls_R_factor_gt           0.0946
_refine_ls_wR_factor_ref         0.2837
_refine_ls_wR_factor_gt          0.2790
_refine_ls_goodness_of_fit_ref   1.046
_refine_ls_restrained_S_all      1.046
_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 0.4441(2) 0.7500 0.74703(18) 0.0313(7) Uani 1 2 d S . .
Cu2 Cu 0.81395(15) 0.37909(14) 0.70506(13) 0.0341(6) Uani 1 1 d . . .
Cu3 Cu 0.1795(2) 0.7500 0.80638(18) 0.0312(7) Uani 1 2 d S . .
N1 N 0.5403(8) 0.6258(8) 0.6869(8) 0.031(2) Uani 1 1 d . . .
N2 N 0.6854(8) 0.4907(8) 0.6590(8) 0.034(2) Uani 1 1 d . . .
N3 N 0.9171(9) 0.4890(8) 0.7857(8) 0.034(2) Uani 1 1 d . . .
N4 N 1.0592(8) 0.6255(8) 0.8228(7) 0.029(2) Uani 1 1 d . . .
C1 C 0.6465(10) 0.5742(10) 0.7232(9) 0.035(3) Uani 1 1 d . . .
H1AA H 0.6897 0.5955 0.7886 0.042 Uiso 1 1 calc R . .
C2 C 0.5064(11) 0.5679(10) 0.5905(8) 0.031(2) Uani 1 1 d . . .
C3 C 0.5991(11) 0.4842(10) 0.5728(9) 0.035(3) Uani 1 1 d . . .
C4 C 0.5936(10) 0.4140(10) 0.4801(10) 0.034(3) Uani 1 1 d . . .
H4AA H 0.6551 0.3578 0.4671 0.041 Uiso 1 1 calc R . .
C5 C 0.9836(10) 0.5748(10) 0.7503(9) 0.032(3) Uani 1 1 d . . .
H5AA H 0.9778 0.5990 0.6769 0.038 Uiso 1 1 calc R . .
C6 C 0.9516(10) 0.4836(10) 0.8975(8) 0.032(3) Uani 1 1 d . . .
C7 C 1.0409(9) 0.5697(10) 0.9190(9) 0.028(2) Uani 1 1 d . . .
C8 C 0.9076(11) 0.4123(10) 0.9778(9) 0.034(3) Uani 1 1 d . . .
H8AA H 0.8465 0.3553 0.9629 0.041 Uiso 1 1 calc R . .
O1 O 0.3212(7) 0.6456(7) 0.8055(7) 0.040(2) Uani 1 1 d . . .
H1AB H 0.3112 0.5886 0.7634 0.048 Uiso 1 1 d R . .
O2 O 0.707(3) 0.2500 0.672(3) 0.038(6) Uani 0.58(4) 2 d SP . 1
H2A H 0.6832 0.2500 0.6053 0.046 Uiso 0.58(4) 2 d SPR . 1
O2' O 0.743(4) 0.2500 0.626(4) 0.038(6) Uani 0.42(4) 2 d SP . 2
H2'A H 0.6691 0.2500 0.5987 0.046 Uiso 0.42(4) 2 d SPR . 2
O3 O 0.9211(12) 0.2500 0.7414(12) 0.050(3) Uani 1 2 d S . .
H3AA H 0.9896 0.2500 0.7782 0.059 Uiso 1 2 d SR . .
O1W O 0.623(3) 0.7500 0.936(2) 0.141(10) Uani 1 2 d S . .
H1WA H 0.5955 0.8149 0.9551 0.170 Uiso 1 1 d R . .
O2W O 0.9157(17) 0.394(3) 0.5250(15) 0.142(11) Uani 0.75 1 d P . .
H2WA H 0.8524 0.3618 0.4955 0.171 Uiso 0.75 1 d PR . .
H2WB H 0.8657 0.4504 0.5289 0.171 Uiso 0.75 1 d PR . .
O3W O 0.153(3) 0.7500 0.606(2) 0.059(8) Uani 0.50 2 d SP . .
H3WB H 0.1419 0.6969 0.5598 0.070 Uiso 0.25 1 d PR A 1
H3WA H 0.1419 0.8031 0.5598 0.070 Uiso 0.25 1 d PR A -1
O4W O 0.2773(13) 0.4093(12) 0.7625(11) 0.090(4) Uani 1 1 d . . .
H4WB H 0.2260 0.3764 0.8030 0.108 Uiso 1 1 d R . .
H4WA H 0.3327 0.3581 0.7566 0.108 Uiso 1 1 d R . .
O5W O 0.4414(19) 0.590(2) 0.9962(14) 0.205(14) Uani 1 1 d . . .
H5WA H 0.3993 0.6015 0.9375 0.246 Uiso 1 1 d R . .
H5WB H 0.3923 0.6193 1.0412 0.246 Uiso 1 1 d R . .
O6W O 0.644(3) 0.2500 0.859(3) 0.15(3) Uani 0.50 2 d SP . .
H6WB H 0.7024 0.2500 0.8139 0.183 Uiso 0.50 2 d SPR . .
H6WA H 0.5696 0.2500 0.8341 0.183 Uiso 0.50 2 d SPR . .
O7W O 0.167(2) 0.2500 0.918(2) 0.152(12) Uani 1 2 d S . .
H7WB H 0.2140 0.2500 0.9745 0.183 Uiso 1 2 d SR . .
H7WA H 0.1880 0.3017 0.8739 0.183 Uiso 0.50 1 d PR . .
O8W O 0.150(2) 0.416(3) 0.5655(17) 0.132(11) Uani 0.65 1 d P . .
H8WB H 0.1821 0.4156 0.6294 0.159 Uiso 0.65 1 d PR . .
H8WA H 0.0758 0.3925 0.5522 0.159 Uiso 0.65 1 d PR . .
O9W O 0.443(3) 0.2500 0.692(2) 0.057(7) Uani 0.50 2 d SP . .
H9WA H 0.4070 0.2500 0.6297 0.069 Uiso 0.50 2 d SPR . .
H9WB H 0.5209 0.2500 0.6840 0.069 Uiso 0.50 2 d SPR . .
O10W O 0.293(3) 0.2500 0.498(3) 0.062(8) Uani 0.50 2 d SP . .
H10A H 0.2405 0.2999 0.5160 0.074 Uiso 0.25 1 d PR . .
H10B H 0.3510 0.2500 0.5473 0.074 Uiso 0.50 2 d SPR . .

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 0.0284(12) 0.0333(13) 0.0326(13) 0.000 0.0047(10) 0.000
Cu2 0.0311(9) 0.0320(10) 0.0385(10) -0.0006(7) -0.0086(7) 0.0007(7)
Cu3 0.0300(13) 0.0304(13) 0.0337(13) 0.000 0.0072(10) 0.000
N1 0.025(5) 0.033(5) 0.036(5) 0.000(4) 0.006(4) 0.000(4)
N2 0.031(5) 0.035(5) 0.035(5) -0.001(4) -0.005(4) 0.007(4)
N3 0.032(5) 0.035(5) 0.035(5) -0.004(4) -0.002(4) 0.002(4)
N4 0.029(5) 0.030(5) 0.028(5) 0.000(4) 0.004(4) 0.000(4)
C1 0.027(6) 0.040(7) 0.037(6) 0.002(5) -0.004(5) 0.002(5)
C2 0.038(6) 0.030(6) 0.026(5) 0.002(5) 0.005(5) -0.003(5)
C3 0.034(6) 0.035(6) 0.037(6) 0.002(5) -0.002(5) -0.003(5)
C4 0.028(6) 0.029(6) 0.044(7) -0.001(5) 0.003(5) 0.006(5)
C5 0.032(6) 0.031(6) 0.032(6) 0.003(5) 0.004(5) 0.002(5)
C6 0.035(6) 0.036(6) 0.024(5) -0.002(5) 0.001(5) 0.003(5)
C7 0.022(5) 0.031(6) 0.032(6) 0.000(5) 0.004(4) 0.003(5)
C8 0.032(6) 0.031(6) 0.041(7) 0.001(5) 0.003(5) -0.008(5)
O1 0.034(4) 0.040(5) 0.047(5) 0.002(4) 0.014(4) 0.001(4)
O2 0.031(16) 0.033(7) 0.05(2) 0.000 -0.013(11) 0.000
O2' 0.031(16) 0.033(7) 0.05(2) 0.000 -0.013(11) 0.000
O3 0.034(7) 0.037(7) 0.075(9) 0.000 -0.024(6) 0.000
O1W 0.15(2) 0.14(2) 0.14(2) 0.000 0.065(19) 0.000
O2W 0.076(12) 0.28(3) 0.070(11) -0.021(16) -0.001(9) 0.059(18)
O3W 0.08(2) 0.066(18) 0.031(13) 0.000 0.013(13) 0.000
O4W 0.104(10) 0.072(8) 0.094(10) 0.002(7) 0.020(8) 0.002(8)
O5W 0.18(2) 0.35(4) 0.075(10) 0.014(17) -0.028(12) 0.14(2)
O6W 0.05(2) 0.34(9) 0.07(2) 0.000 -0.017(18) 0.000
O7W 0.093(16) 0.24(3) 0.13(2) 0.000 0.065(16) 0.000
O8W 0.086(15) 0.24(4) 0.067(13) 0.018(18) -0.008(11) 0.02(2)
O9W 0.055(17) 0.051(16) 0.066(18) 0.000 -0.004(14) 0.000
O10W 0.055(17) 0.052(17) 0.08(2) 0.000 0.042(16) 0.000

_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 N1 1.947(9) 4_575 ?
Cu1 N1 1.947(9) . ?
Cu1 O1 1.958(8) . ?
Cu1 O1 1.958(8) 4_575 ?
Cu1 Cu3 2.965(3) . ?
Cu2 O2 1.931(18) . ?
Cu2 O2' 1.94(3) . ?
Cu2 O3 1.943(7) . ?
Cu2 N3 1.948(10) . ?
Cu2 N2 1.970(9) . ?
Cu2 Cu2 3.023(3) 4_565 ?
Cu3 O1 1.953(8) 4_575 ?
Cu3 O1 1.953(8) . ?
Cu3 N4 1.964(9) 1_455 ?
Cu3 N4 1.964(9) 4_475 ?
N1 C1 1.354(14) . ?
N1 C2 1.406(14) . ?
N2 C1 1.335(15) . ?
N2 C3 1.388(14) . ?
N3 C5 1.317(15) . ?
N3 C6 1.417(14) . ?
N4 C5 1.326(15) . ?
N4 C7 1.376(14) . ?
N4 Cu3 1.964(9) 1_655 ?
C1 H1AA 0.9500 . ?
C2 C4 1.375(16) 3_666 ?
C2 C3 1.420(17) . ?
C3 C4 1.409(17) . ?
C4 C2 1.375(16) 3_666 ?
C4 H4AA 0.9500 . ?
C5 H5AA 0.9500 . ?
C6 C8 1.392(16) . ?
C6 C7 1.411(16) . ?
C7 C8 1.385(16) 3_767 ?
C8 C7 1.385(16) 3_767 ?
C8 H8AA 0.9500 . ?
O1 H1AB 0.8501 . ?
O2 Cu2 1.931(18) 4_565 ?
O2 H2A 0.8501 . ?
O2 H2'A 0.9771 . ?
O2' Cu2 1.94(3) 4_565 ?
O2' H2A 0.6810 . ?
O2' H2'A 0.8499 . ?
O3 Cu2 1.943(7) 4_565 ?
O3 H3AA 0.8502 . ?
O1W H1WA 0.8500 . ?
O2W H2WA 0.8500 . ?
O2W H2WB 0.8500 . ?
O3W H3WB 0.8500 . ?
O3W H3WA 0.8500 . ?
O4W H4WB 0.8500 . ?
O4W H4WA 0.8500 . ?
O5W H5WA 0.8500 . ?
O5W H5WB 0.8499 . ?
O6W H6WB 0.8500 . ?
O6W H6WA 0.8500 . ?
O7W H7WB 0.8497 . ?
O7W H7WA 0.8501 . ?
O8W H8WB 0.8501 . ?
O8W H8WA 0.8498 . ?
O9W H9WA 0.8499 . ?
O9W H9WB 0.8498 . ?
O10W H10A 0.8500 . ?
O10W H10B 0.8500 . ?

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
N1 Cu1 N1 96.6(5) 4_575 . ?
N1 Cu1 O1 169.2(4) 4_575 . ?
N1 Cu1 O1 92.9(4) . . ?
N1 Cu1 O1 92.9(4) 4_575 4_575 ?
N1 Cu1 O1 169.2(4) . 4_575 ?
O1 Cu1 O1 77.2(5) . 4_575 ?
N1 Cu1 Cu3 128.5(3) 4_575 . ?
N1 Cu1 Cu3 128.5(3) . . ?
O1 Cu1 Cu3 40.7(2) . . ?
O1 Cu1 Cu3 40.7(2) 4_575 . ?
O2 Cu2 O2' 20.6(10) . . ?
O2 Cu2 O3 77.4(7) . . ?
O2' Cu2 O3 74.3(11) . . ?
O2 Cu2 N3 161.4(11) . . ?
O2' Cu2 N3 167.9(12) . . ?
O3 Cu2 N3 94.3(4) . . ?
O2 Cu2 N2 93.1(7) . . ?
O2' Cu2 N2 96.5(11) . . ?
O3 Cu2 N2 170.5(4) . . ?
N3 Cu2 N2 95.1(4) . . ?
O2 Cu2 Cu2 38.5(7) . 4_565 ?
O2' Cu2 Cu2 38.9(10) . 4_565 ?
O3 Cu2 Cu2 38.9(3) . 4_565 ?
N3 Cu2 Cu2 131.4(3) . 4_565 ?
N2 Cu2 Cu2 131.5(3) . 4_565 ?
O1 Cu3 O1 77.5(5) 4_575 . ?
O1 Cu3 N4 169.0(4) 4_575 1_455 ?
O1 Cu3 N4 93.0(4) . 1_455 ?
O1 Cu3 N4 93.0(4) 4_575 4_475 ?
O1 Cu3 N4 169.0(4) . 4_475 ?
N4 Cu3 N4 95.8(5) 1_455 4_475 ?
O1 Cu3 Cu1 40.8(2) 4_575 . ?
O1 Cu3 Cu1 40.8(2) . . ?
N4 Cu3 Cu1 131.9(3) 1_455 . ?
N4 Cu3 Cu1 131.9(3) 4_475 . ?
C1 N1 C2 104.7(9) . . ?
C1 N1 Cu1 131.4(8) . . ?
C2 N1 Cu1 123.9(7) . . ?
C1 N2 C3 106.2(9) . . ?
C1 N2 Cu2 123.1(7) . . ?
C3 N2 Cu2 128.8(8) . . ?
C5 N3 C6 103.4(9) . . ?
C5 N3 Cu2 129.8(8) . . ?
C6 N3 Cu2 126.3(8) . . ?
C5 N4 C7 105.4(9) . . ?
C5 N4 Cu3 130.7(8) . 1_655 ?
C7 N4 Cu3 123.8(7) . 1_655 ?
N2 C1 N1 114.2(10) . . ?
N2 C1 H1AA 122.9 . . ?
N1 C1 H1AA 122.9 . . ?
C4 C2 N1 129.3(11) 3_666 . ?
C4 C2 C3 123.1(10) 3_666 . ?
N1 C2 C3 107.6(9) . . ?
N2 C3 C4 131.4(11) . . ?
N2 C3 C2 107.3(10) . . ?
C4 C3 C2 121.3(10) . . ?
C2 C4 C3 115.6(10) 3_666 . ?
C2 C4 H4AA 122.2 3_666 . ?
C3 C4 H4AA 122.2 . . ?
N3 C5 N4 116.4(10) . . ?
N3 C5 H5AA 121.8 . . ?
N4 C5 H5AA 121.8 . . ?
C8 C6 C7 122.8(10) . . ?
C8 C6 N3 129.6(11) . . ?
C7 C6 N3 107.6(10) . . ?
N4 C7 C8 131.1(10) . 3_767 ?
N4 C7 C6 107.1(9) . . ?
C8 C7 C6 121.8(10) 3_767 . ?
C7 C8 C6 115.4(10) 3_767 . ?
C7 C8 H8AA 122.3 3_767 . ?
C6 C8 H8AA 122.3 . . ?
Cu3 O1 Cu1 98.6(4) . . ?
Cu3 O1 H1AB 114.4 . . ?
Cu1 O1 H1AB 109.6 . . ?
Cu2 O2 Cu2 103.0(13) . 4_565 ?
Cu2 O2 H2A 111.3 . . ?
Cu2 O2 H2A 111.3 4_565 . ?
Cu2 O2 H2'A 115.1 . . ?
Cu2 O2 H2'A 115.1 4_565 . ?
H2A O2 H2'A 7.1 . . ?
Cu2 O2' Cu2 102(2) . 4_565 ?
Cu2 O2' H2A 122.3 . . ?
Cu2 O2' H2A 122.3 4_565 . ?
Cu2 O2' H2'A 122.9 . . ?
Cu2 O2' H2'A 122.9 4_565 . ?
H2A O2' H2'A 1.4 . . ?
Cu2 O3 Cu2 102.1(5) 4_565 . ?
Cu2 O3 H3AA 128.1 4_565 . ?
Cu2 O3 H3AA 128.1 . . ?
H2WA O2W H2WB 82.8 . . ?
H3WB O3W H3WA 94.0 . . ?
H4WB O4W H4WA 101.7 . . ?
H5WA O5W H5WB 99.9 . . ?
H6WB O6W H6WA 118.1 . . ?
H7WB O7W H7WA 110.9 . . ?
H8WB O8W H8WA 121.8 . . ?
H9WA O9W H9WB 107.9 . . ?
H10A O10W H10B 107.0 . . ?

_diffrn_measured_fraction_theta_max 0.988
_diffrn_reflns_theta_full        60.84
_diffrn_measured_fraction_theta_full 0.988
_refine_diff_density_max         1.760
_refine_diff_density_min         -1.233
_refine_diff_density_rms         0.221
_database_code_depnum_ccdc_archive 'CCDC 956255'
#######################################################################
#
#                 Cambridge Crystallographic Data Centre
#                                CCDC 
# 
#######################################################################
# 
#  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.
#
#  This CIF is provided on the understanding that it is used for bona
#  fide research purposes only. It may contain copyright material
#  of the CCDC or of third parties, and may not be copied or further
#  disseminated in any form, whether machine-readable or not,
#  except for the purpose of generating routine backup copies
#  on your local computer system.
# 
#  For further information on the CCDC, data deposition and
#  data retrieval see:
#                         www.ccdc.cam.ac.uk
#
#  Bona fide researchers may freely download Mercury and enCIFer
#  from this site to visualise CIF-encoded structures and 
#  to carry out CIF format checking respectively.
#
data_2

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C16 H16 Cu2 N4 O2'
_chemical_formula_weight         423.41

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'
Cu Cu 0.3201 1.2651 '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/m

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

_cell_length_a                   16.377(3)
_cell_length_b                   12.209(2)
_cell_length_c                   10.2681(18)
_cell_angle_alpha                90.00
_cell_angle_beta                 127.226(2)
_cell_angle_gamma                90.00
_cell_volume                     1634.8(5)
_cell_formula_units_Z            4
_cell_measurement_temperature    128(2)
_cell_measurement_reflns_used    ?
_cell_measurement_theta_min      ?
_cell_measurement_theta_max      ?

_exptl_crystal_description       ?
_exptl_crystal_colour            ?
_exptl_crystal_size_max          0.25
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.20
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.720
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             856
_exptl_absorpt_coefficient_mu    2.617
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.5607
_exptl_absorpt_correction_T_max  0.6226
_exptl_absorpt_process_details   SADABS

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      128(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  ?
_diffrn_measurement_method       ?
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            6292
_diffrn_reflns_av_R_equivalents  0.0525
_diffrn_reflns_av_sigmaI/netI    0.0523
_diffrn_reflns_limit_h_min       -20
_diffrn_reflns_limit_h_max       20
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_theta_min         2.29
_diffrn_reflns_theta_max         26.00
_reflns_number_total             1675
_reflns_number_gt                1343
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       SMART
_computing_cell_refinement       SAINT
_computing_data_reduction        SAINT
_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^)+(0.0532P)^2^+1.7594P] 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         1675
_refine_ls_number_parameters     117
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0552
_refine_ls_R_factor_gt           0.0385
_refine_ls_wR_factor_ref         0.1009
_refine_ls_wR_factor_gt          0.0929
_refine_ls_goodness_of_fit_ref   1.028
_refine_ls_restrained_S_all      1.028
_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 0.46137(4) 0.5000 0.82284(7) 0.0169(2) Uani 1 2 d S . .
Cu2 Cu 0.5000 0.12436(5) 0.5000 0.0188(2) Uani 1 2 d S . .
O1 O 0.5000 0.5966(3) 1.0000 0.0245(8) Uani 1 2 d S . .
O2 O 0.4657(3) 0.0000 0.5746(4) 0.0222(8) Uani 1 2 d S . .
N1 N 0.4214(2) 0.3807(2) 0.6686(4) 0.0178(6) Uani 1 1 d . . .
N2 N 0.4332(2) 0.2347(2) 0.5450(4) 0.0196(7) Uani 1 1 d . . .
C1 C 0.4778(3) 0.3247(3) 0.6372(4) 0.0208(8) Uani 1 1 d . . .
H1A H 0.5449 0.3471 0.6773 0.025 Uiso 1 1 calc R . .
C2 C 0.3299(3) 0.3226(3) 0.5895(4) 0.0173(7) Uani 1 1 d . . .
C3 C 0.3369(3) 0.2316(3) 0.5115(4) 0.0184(8) Uani 1 1 d . . .
C4 C 0.2574(3) 0.1568(3) 0.4196(4) 0.0179(8) Uani 1 1 d . . .
H4A H 0.2621 0.0960 0.3666 0.021 Uiso 1 1 calc R . .
C5 C 0.5000 0.7136(4) 1.0000 0.0330(14) Uani 1 2 d S . .
H5A H 0.5252 0.7403 1.1084 0.050 Uiso 0.50 1 calc PR . .
H5B H 0.4300 0.7403 0.9182 0.050 Uiso 0.50 1 calc PR . .
H5C H 0.5447 0.7403 0.9734 0.050 Uiso 0.50 1 calc PR . .
C6 C 0.4692(4) 0.0000 0.7174(7) 0.0280(13) Uani 1 2 d S . .
H6A H 0.4664 -0.0756 0.7467 0.042 Uiso 0.50 1 calc PR . .
H6B H 0.4104 0.0410 0.6949 0.042 Uiso 0.50 1 calc PR . .
H6C H 0.5330 0.0345 0.8082 0.042 Uiso 0.50 1 calc PR . .
C7 C 0.2538(4) 0.1123(5) 0.9094(7) 0.0580(15) Uani 1 1 d . . .
H7A H 0.2552 0.1901 0.9114 0.070 Uiso 1 1 calc R . .
C8 C 0.2308(4) 0.0555(5) 1.0006(7) 0.0605(15) Uani 1 1 d . . .
H8A H 0.2151 0.0944 1.0630 0.073 Uiso 1 1 calc R . .
C9 C 0.2746(3) 0.0559(4) 0.8158(5) 0.0445(12) Uani 1 1 d . . .
H9A H 0.2889 0.0948 0.7516 0.053 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 0.0165(3) 0.0150(3) 0.0234(4) 0.000 0.0143(3) 0.000
Cu2 0.0186(4) 0.0162(3) 0.0322(4) 0.000 0.0210(3) 0.000
O1 0.036(2) 0.0143(18) 0.027(2) 0.000 0.0210(19) 0.000
O2 0.031(2) 0.0170(18) 0.037(2) 0.000 0.030(2) 0.000
N1 0.0180(16) 0.0164(15) 0.0264(17) -0.0008(13) 0.0174(14) -0.0011(12)
N2 0.0165(16) 0.0206(16) 0.0293(17) -0.0004(13) 0.0178(14) 0.0000(13)
C1 0.0158(19) 0.022(2) 0.028(2) 0.0005(16) 0.0152(17) -0.0003(16)
C2 0.0156(18) 0.0170(18) 0.0206(19) 0.0022(14) 0.0117(16) -0.0002(14)
C3 0.0169(18) 0.0192(18) 0.0238(19) 0.0007(15) 0.0148(16) 0.0022(15)
C4 0.0192(18) 0.0169(18) 0.025(2) -0.0013(15) 0.0171(17) 0.0015(15)
C5 0.045(4) 0.016(3) 0.034(3) 0.000 0.022(3) 0.000
C6 0.029(3) 0.034(3) 0.032(3) 0.000 0.024(3) 0.000
C7 0.052(3) 0.062(4) 0.063(4) 0.002(3) 0.037(3) 0.010(3)
C8 0.061(4) 0.079(4) 0.066(3) -0.003(3) 0.051(3) 0.008(3)
C9 0.040(3) 0.060(3) 0.038(3) 0.009(2) 0.026(2) 0.006(2)

_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 1.926(2) . ?
Cu1 O1 1.926(2) 5_667 ?
Cu1 N1 1.950(3) . ?
Cu1 N1 1.950(3) 6_565 ?
Cu1 Cu1 3.0444(13) 5_667 ?
Cu2 O2 1.931(2) 5_656 ?
Cu2 O2 1.931(2) . ?
Cu2 N2 1.959(3) 2_656 ?
Cu2 N2 1.959(3) . ?
Cu2 Cu2 3.0366(13) 5_656 ?
O1 C5 1.428(6) . ?
O1 Cu1 1.926(2) 5_667 ?
O2 C6 1.432(6) . ?
O2 Cu2 1.931(2) 5_656 ?
N1 C1 1.337(4) . ?
N1 C2 1.392(4) . ?
N2 C1 1.342(4) . ?
N2 C3 1.397(4) . ?
C1 H1A 0.9500 . ?
C2 C4 1.398(5) 7_556 ?
C2 C3 1.414(5) . ?
C3 C4 1.390(5) . ?
C4 C2 1.398(5) 7_556 ?
C4 H4A 0.9500 . ?
C5 H5A 0.9800 . ?
C5 H5B 0.9800 . ?
C5 H5C 0.9800 . ?
C6 H6A 0.9800 . ?
C6 H6B 0.9800 . ?
C6 H6C 0.9800 . ?
C7 C9 1.382(6) . ?
C7 C8 1.387(7) . ?
C7 H7A 0.9500 . ?
C8 C8 1.355(11) 6 ?
C8 H8A 0.9500 . ?
C9 C9 1.364(9) 6 ?
C9 H9A 0.9500 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
O1 Cu1 O1 75.56(16) . 5_667 ?
O1 Cu1 N1 169.01(11) . . ?
O1 Cu1 N1 93.84(12) 5_667 . ?
O1 Cu1 N1 93.84(12) . 6_565 ?
O1 Cu1 N1 169.01(11) 5_667 6_565 ?
N1 Cu1 N1 96.60(17) . 6_565 ?
O1 Cu1 Cu1 37.78(8) . 5_667 ?
O1 Cu1 Cu1 37.78(8) 5_667 5_667 ?
N1 Cu1 Cu1 131.55(8) . 5_667 ?
N1 Cu1 Cu1 131.55(8) 6_565 5_667 ?
O2 Cu2 O2 76.34(15) 5_656 . ?
O2 Cu2 N2 96.24(11) 5_656 2_656 ?
O2 Cu2 N2 166.51(13) . 2_656 ?
O2 Cu2 N2 166.51(13) 5_656 . ?
O2 Cu2 N2 96.24(11) . . ?
N2 Cu2 N2 93.13(16) 2_656 . ?
O2 Cu2 Cu2 38.17(7) 5_656 5_656 ?
O2 Cu2 Cu2 38.17(7) . 5_656 ?
N2 Cu2 Cu2 133.44(8) 2_656 5_656 ?
N2 Cu2 Cu2 133.44(8) . 5_656 ?
C5 O1 Cu1 127.78(8) . . ?
C5 O1 Cu1 127.78(8) . 5_667 ?
Cu1 O1 Cu1 104.44(16) . 5_667 ?
C6 O2 Cu2 124.42(13) . 5_656 ?
C6 O2 Cu2 124.42(13) . . ?
Cu2 O2 Cu2 103.66(15) 5_656 . ?
C1 N1 C2 104.9(3) . . ?
C1 N1 Cu1 129.6(2) . . ?
C2 N1 Cu1 124.6(2) . . ?
C1 N2 C3 104.4(3) . . ?
C1 N2 Cu2 125.8(2) . . ?
C3 N2 Cu2 129.2(2) . . ?
N1 C1 N2 115.3(3) . . ?
N1 C1 H1A 122.3 . . ?
N2 C1 H1A 122.3 . . ?
N1 C2 C4 130.1(3) . 7_556 ?
N1 C2 C3 107.6(3) . . ?
C4 C2 C3 122.2(3) 7_556 . ?
C4 C3 N2 129.7(3) . . ?
C4 C3 C2 122.5(3) . . ?
N2 C3 C2 107.8(3) . . ?
C3 C4 C2 115.3(3) . 7_556 ?
C3 C4 H4A 122.4 . . ?
C2 C4 H4A 122.4 7_556 . ?
O1 C5 H5A 109.5 . . ?
O1 C5 H5B 109.5 . . ?
H5A C5 H5B 109.5 . . ?
O1 C5 H5C 109.5 . . ?
H5A C5 H5C 109.5 . . ?
H5B C5 H5C 109.5 . . ?
O2 C6 H6A 109.5 . . ?
O2 C6 H6B 109.5 . . ?
H6A C6 H6B 109.5 . . ?
O2 C6 H6C 109.5 . . ?
H6A C6 H6C 109.5 . . ?
H6B C6 H6C 109.5 . . ?
C9 C7 C8 120.1(5) . . ?
C9 C7 H7A 119.9 . . ?
C8 C7 H7A 119.9 . . ?
C8 C8 C7 120.0(3) 6 . ?
C8 C8 H8A 120.0 6 . ?
C7 C8 H8A 120.0 . . ?
C9 C9 C7 119.9(3) 6 . ?
C9 C9 H9A 120.1 6 . ?
C7 C9 H9A 120.1 . . ?

_diffrn_measured_fraction_theta_max 0.992
_diffrn_reflns_theta_full        26.00
_diffrn_measured_fraction_theta_full 0.992
_refine_diff_density_max         0.703
_refine_diff_density_min         -0.527
_refine_diff_density_rms         0.117
_database_code_depnum_ccdc_archive 'CCDC 956256'