# Electronic Supplementary Material (ESI) for CrystEngComm.
# This journal is © The Royal Society of Chemistry 2014

#######################################################################
#
#                 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_1

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C18 H26 Cl4 Cu2 N4 O2'
_chemical_formula_weight         599.31

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cu Cu 0.3201 1.2651 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_H-M   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                   13.478(4)
_cell_length_b                   11.259(4)
_cell_length_c                   15.046(3)
_cell_angle_alpha                90.00
_cell_angle_beta                 93.77(3)
_cell_angle_gamma                90.00
_cell_volume                     2278.3(11)
_cell_formula_units_Z            4
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    3698
_cell_measurement_theta_min      3.03
_cell_measurement_theta_max      27.68

_exptl_crystal_description       platelet
_exptl_crystal_colour            green
_exptl_crystal_size_max          0.20
_exptl_crystal_size_mid          0.19
_exptl_crystal_size_min          0.12
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.747
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1216
_exptl_absorpt_coefficient_mu    2.359
_exptl_absorpt_correction_type   Empirical
_exptl_absorpt_correction_T_min  0.0362
_exptl_absorpt_correction_T_max  0.0966
_exptl_absorpt_process_details   'ABSCOR; Higashi, 1995'

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      293(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 R-AXIS RAPID IP'
_diffrn_measurement_method       'ω scans'
_diffrn_detector_area_resol_mean 0.77
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            10999
_diffrn_reflns_av_R_equivalents  0.1311
_diffrn_reflns_av_sigmaI/netI    0.0965
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_h_max       17
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_theta_min         3.03
_diffrn_reflns_theta_max         27.54
_reflns_number_total             2629
_reflns_number_gt                2320
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'crystalstructure 3.6.0 (Rigaku/MSC, 2004)'
_computing_cell_refinement       'crystalstructure 3.6.0 (Rigaku/MSC, 2004)'
_computing_data_reduction        'Crystalstructure 2004'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1997)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    'XP (Sheldrick, 1998)'
_computing_publication_material  'XP (Sheldrick, 1998)'

_refine_special_details          
; 
 Refinement of F² against ALL reflections.  The weighted R-factor wR and 
 goodness of fit S are based on F², conventional R-factors R are based 
 on F, with F set to zero for negative F². The threshold expression of 
 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is 
 not relevant to the choice of reflections for refinement.  R-factors based 
 on F² 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/[σ²(Fo²)+(0.0892P)²+0.2208P] where P=(Fo²+2Fc²)/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         2629
_refine_ls_number_parameters     138
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0586
_refine_ls_R_factor_gt           0.0544
_refine_ls_wR_factor_ref         0.1464
_refine_ls_wR_factor_gt          0.1409
_refine_ls_goodness_of_fit_ref   1.039
_refine_ls_restrained_S_all      1.039
_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
Cl2 Cl 0.58054(5) -0.04716(7) 0.33554(4) 0.0375(2) Uani 1 1 d . . .
Cu1 Cu 0.5000 -0.18230(4) 0.2500 0.0275(2) Uani 1 2 d S . .
Cu2 Cu 0.5000 0.0000 0.5000 0.0286(2) Uani 1 2 d S . .
Cl1 Cl 0.52002(6) -0.31796(7) 0.14193(5) 0.0367(2) Uani 1 1 d . . .
O1 O 0.47696(14) 0.17278(18) 0.47466(12) 0.0294(4) Uani 1 1 d . . .
N1 N 0.36155(16) -0.0353(2) 0.46416(14) 0.0278(5) Uani 1 1 d . . .
N3 N 0.30124(15) 0.0404(2) 0.41547(14) 0.0265(5) Uani 1 1 d . . .
C1 C 0.4345(2) 0.3287(3) 0.3696(2) 0.0366(7) Uani 1 1 d . . .
H1A H 0.4889 0.3001 0.3362 0.044 Uiso 1 1 calc R . .
H1B H 0.4606 0.3896 0.4102 0.044 Uiso 1 1 calc R . .
C2 C 0.3061(2) 0.2894(4) 0.2462(2) 0.0431(8) Uani 1 1 d . . .
H2A H 0.3544 0.2564 0.2080 0.052 Uiso 1 1 calc R . .
H2B H 0.2531 0.3252 0.2085 0.052 Uiso 1 1 calc R . .
C4 C 0.2030(2) -0.0772(3) 0.48499(19) 0.0373(7) Uani 1 1 d . . .
H4A H 0.1468 -0.1132 0.5055 0.045 Uiso 1 1 calc R . .
C5 C 0.34463(18) 0.1340(3) 0.36273(16) 0.0259(5) Uani 1 1 d . . .
H5A H 0.3945 0.0983 0.3264 0.031 Uiso 1 1 calc R . .
C7 C 0.2637(2) 0.1908(3) 0.30068(19) 0.0348(7) Uani 1 1 d . . .
H7A H 0.2340 0.1308 0.2610 0.042 Uiso 1 1 calc R . .
H7B H 0.2120 0.2227 0.3357 0.042 Uiso 1 1 calc R . .
C8 C 0.39489(18) 0.2273(3) 0.42261(16) 0.0260(5) Uani 1 1 d . . .
H8A H 0.3469 0.2583 0.4629 0.031 Uiso 1 1 calc R . .
C10 C 0.2063(2) 0.0158(3) 0.4274(2) 0.0339(6) Uani 1 1 d . . .
H10A H 0.1515 0.0555 0.4009 0.041 Uiso 1 1 calc R . .
C14 C 0.3550(3) 0.3829(3) 0.3052(2) 0.0455(8) Uani 1 1 d . . .
H14A H 0.3053 0.4220 0.3387 0.055 Uiso 1 1 calc R . .
H14B H 0.3851 0.4423 0.2688 0.055 Uiso 1 1 calc R . .
C15 C 0.3011(2) -0.1066(3) 0.50629(18) 0.0337(6) Uani 1 1 d . . .
H15A H 0.3221 -0.1676 0.5447 0.040 Uiso 1 1 calc R . .


_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
Cl2 Cu1 2.2286(9) . ?
Cl2 Cu2 2.8172(10) . ?
Cu1 Cl2 2.2286(9) 2_655 ?
Cu1 Cl1 2.2600(9) . ?
Cu1 Cl1 2.2600(9) 2_655 ?
Cu2 N1 1.949(2) . ?
Cu2 N1 1.949(2) 5_656 ?
Cu2 O1 2.003(2) . ?
Cu2 O1 2.003(2) 5_656 ?
O1 C8 1.449(3) . ?
N1 C15 1.334(4) . ?
N1 N3 1.358(3) . ?
N3 C10 1.333(4) . ?
N3 C5 1.464(3) . ?
C1 C8 1.511(4) . ?
C1 C14 1.524(4) . ?
C1 H1A 0.9700 . ?
C1 H1B 0.9700 . ?
C2 C14 1.502(5) . ?
C2 C7 1.514(5) . ?
C2 H2A 0.9700 . ?
C2 H2B 0.9700 . ?
C4 C10 1.362(5) . ?
C4 C15 1.380(4) . ?
C4 H4A 0.9300 . ?
C5 C8 1.515(4) . ?
C5 C7 1.529(4) . ?
C5 H5A 0.9800 . ?
C7 H7A 0.9700 . ?
C7 H7B 0.9700 . ?
C8 H8A 0.9800 . ?
C10 H10A 0.9300 . ?
C14 H14A 0.9700 . ?
C14 H14B 0.9700 . ?
C15 H15A 0.9300 . ?

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
Cu1 Cl2 Cu2 115.77(3) . . ?
Cl2 Cu1 Cl2 93.88(5) . 2_655 ?
Cl2 Cu1 Cl1 143.16(3) . . ?
Cl2 Cu1 Cl1 97.04(3) 2_655 . ?
Cl2 Cu1 Cl1 97.04(3) . 2_655 ?
Cl2 Cu1 Cl1 143.16(3) 2_655 2_655 ?
Cl1 Cu1 Cl1 94.96(5) . 2_655 ?
N1 Cu2 N1 180.00(12) . 5_656 ?
N1 Cu2 O1 90.66(9) . . ?
N1 Cu2 O1 89.34(9) 5_656 . ?
N1 Cu2 O1 89.34(9) . 5_656 ?
N1 Cu2 O1 90.66(9) 5_656 5_656 ?
O1 Cu2 O1 180.0 . 5_656 ?
N1 Cu2 Cl2 97.81(7) . . ?
N1 Cu2 Cl2 82.19(7) 5_656 . ?
O1 Cu2 Cl2 94.58(6) . . ?
O1 Cu2 Cl2 85.42(6) 5_656 . ?
C8 O1 Cu2 128.14(16) . . ?
C15 N1 N3 105.7(2) . . ?
C15 N1 Cu2 126.50(18) . . ?
N3 N1 Cu2 123.36(19) . . ?
C10 N3 N1 110.1(2) . . ?
C10 N3 C5 130.0(2) . . ?
N1 N3 C5 119.8(2) . . ?
C8 C1 C14 112.3(3) . . ?
C8 C1 H1A 109.1 . . ?
C14 C1 H1A 109.1 . . ?
C8 C1 H1B 109.1 . . ?
C14 C1 H1B 109.1 . . ?
H1A C1 H1B 107.9 . . ?
C14 C2 C7 111.2(3) . . ?
C14 C2 H2A 109.4 . . ?
C7 C2 H2A 109.4 . . ?
C14 C2 H2B 109.4 . . ?
C7 C2 H2B 109.4 . . ?
H2A C2 H2B 108.0 . . ?
C10 C4 C15 105.1(3) . . ?
C10 C4 H4A 127.4 . . ?
C15 C4 H4A 127.4 . . ?
N3 C5 C8 110.8(2) . . ?
N3 C5 C7 109.7(2) . . ?
C8 C5 C7 110.3(2) . . ?
N3 C5 H5A 108.6 . . ?
C8 C5 H5A 108.6 . . ?
C7 C5 H5A 108.6 . . ?
C2 C7 C5 111.0(2) . . ?
C2 C7 H7A 109.4 . . ?
C5 C7 H7A 109.4 . . ?
C2 C7 H7B 109.4 . . ?
C5 C7 H7B 109.4 . . ?
H7A C7 H7B 108.0 . . ?
O1 C8 C1 108.8(2) . . ?
O1 C8 C5 108.9(2) . . ?
C1 C8 C5 111.7(2) . . ?
O1 C8 H8A 109.2 . . ?
C1 C8 H8A 109.2 . . ?
C5 C8 H8A 109.2 . . ?
N3 C10 C4 108.5(3) . . ?
N3 C10 H10A 125.8 . . ?
C4 C10 H10A 125.8 . . ?
C2 C14 C1 111.0(3) . . ?
C2 C14 H14A 109.4 . . ?
C1 C14 H14A 109.4 . . ?
C2 C14 H14B 109.4 . . ?
C1 C14 H14B 109.4 . . ?
H14A C14 H14B 108.0 . . ?
N1 C15 C4 110.6(3) . . ?
N1 C15 H15A 124.7 . . ?
C4 C15 H15A 124.7 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
Cu2 Cl2 Cu1 Cl2 99.48(4) . . . 2_655 ?
Cu2 Cl2 Cu1 Cl1 -153.34(4) . . . . ?
Cu2 Cl2 Cu1 Cl1 -45.27(4) . . . 2_655 ?
Cu1 Cl2 Cu2 N1 -29.17(8) . . . . ?
Cu1 Cl2 Cu2 N1 150.83(8) . . . 5_656 ?
Cu1 Cl2 Cu2 O1 -120.46(7) . . . . ?
Cu1 Cl2 Cu2 O1 59.54(7) . . . 5_656 ?
N1 Cu2 O1 C8 -16.7(2) . . . . ?
N1 Cu2 O1 C8 163.3(2) 5_656 . . . ?
O1 Cu2 O1 C8 -137(100) 5_656 . . . ?
Cl2 Cu2 O1 C8 81.22(19) . . . . ?
N1 Cu2 N1 C15 -20(100) 5_656 . . . ?
O1 Cu2 N1 C15 -135.9(3) . . . . ?
O1 Cu2 N1 C15 44.1(3) 5_656 . . . ?
Cl2 Cu2 N1 C15 129.4(2) . . . . ?
N1 Cu2 N1 N3 133(100) 5_656 . . . ?
O1 Cu2 N1 N3 17.2(2) . . . . ?
O1 Cu2 N1 N3 -162.8(2) 5_656 . . . ?
Cl2 Cu2 N1 N3 -77.5(2) . . . . ?
C15 N1 N3 C10 -0.1(3) . . . . ?
Cu2 N1 N3 C10 -157.8(2) . . . . ?
C15 N1 N3 C5 178.1(2) . . . . ?
Cu2 N1 N3 C5 20.3(3) . . . . ?
C10 N3 C5 C8 108.8(3) . . . . ?
N1 N3 C5 C8 -68.9(3) . . . . ?
C10 N3 C5 C7 -13.2(4) . . . . ?
N1 N3 C5 C7 169.0(2) . . . . ?
C14 C2 C7 C5 -57.8(4) . . . . ?
N3 C5 C7 C2 179.1(3) . . . . ?
C8 C5 C7 C2 56.7(3) . . . . ?
Cu2 O1 C8 C1 -141.2(2) . . . . ?
Cu2 O1 C8 C5 -19.2(3) . . . . ?
C14 C1 C8 O1 173.9(3) . . . . ?
C14 C1 C8 C5 53.7(4) . . . . ?
N3 C5 C8 O1 63.5(3) . . . . ?
C7 C5 C8 O1 -174.8(2) . . . . ?
N3 C5 C8 C1 -176.4(2) . . . . ?
C7 C5 C8 C1 -54.7(3) . . . . ?
N1 N3 C10 C4 0.1(3) . . . . ?
C5 N3 C10 C4 -177.7(3) . . . . ?
C15 C4 C10 N3 -0.1(3) . . . . ?
C7 C2 C14 C1 55.6(4) . . . . ?
C8 C1 C14 C2 -53.7(4) . . . . ?
N3 N1 C15 C4 0.0(3) . . . . ?
Cu2 N1 C15 C4 156.8(2) . . . . ?
C10 C4 C15 N1 0.1(4) . . . . ?

_diffrn_measured_fraction_theta_max 0.997
_diffrn_reflns_theta_full        27.54
_diffrn_measured_fraction_theta_full 0.997
_refine_diff_density_max         1.819
_refine_diff_density_min         -1.001
_refine_diff_density_rms         0.180
_database_code_depnum_ccdc_archive 'CCDC 987104'
#######################################################################
#
#                 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            'C21 H30 Cl Cu2 N7 O7'
_chemical_formula_weight         655.05

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'
Cl Cl 0.1484 0.1585 '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                   9.2753(6)
_cell_length_b                   22.6255(17)
_cell_length_c                   13.3340(8)
_cell_angle_alpha                90.00
_cell_angle_beta                 110.287(2)
_cell_angle_gamma                90.00
_cell_volume                     2624.7(3)
_cell_formula_units_Z            4
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    11897
_cell_measurement_theta_min      3.16
_cell_measurement_theta_max      27.44

_exptl_crystal_description       block
_exptl_crystal_colour            green
_exptl_crystal_size_max          0.21
_exptl_crystal_size_mid          0.19
_exptl_crystal_size_min          0.14
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.658
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1344
_exptl_absorpt_coefficient_mu    1.777
_exptl_absorpt_correction_type   empirical
_exptl_absorpt_correction_T_min  0.4342
_exptl_absorpt_correction_T_max  1.0000
_exptl_absorpt_process_details   'ABSCOR; Higashi, 1995'

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      293(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 R-AXIS RAPID IP'
_diffrn_measurement_method       'ω scans'
_diffrn_detector_area_resol_mean 0.77
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            25243
_diffrn_reflns_av_R_equivalents  0.1512
_diffrn_reflns_av_sigmaI/netI    0.1251
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_k_min       -29
_diffrn_reflns_limit_k_max       29
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_theta_min         3.15
_diffrn_reflns_theta_max         27.44
_reflns_number_total             5925
_reflns_number_gt                2886
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'crystalstructure 3.6.0 (Rigaku/MSC, 2004)'
_computing_cell_refinement       'crystalstructure 3.6.0 (Rigaku/MSC, 2004)'
_computing_data_reduction        'Crystalstructure 2004'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1997)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    'XP (Sheldrick, 1998)'
_computing_publication_material  'XP (Sheldrick, 1998)'

_refine_special_details          
; 
 Refinement of F² against ALL reflections.  The weighted R-factor wR and 
 goodness of fit S are based on F², conventional R-factors R are based 
 on F, with F set to zero for negative F². The threshold expression of 
 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is 
 not relevant to the choice of reflections for refinement.  R-factors based 
 on F² are statistically about twice as large as those based on F, and R- 
 factors based on ALL data will be even larger. 

 The atoms (N5 and O5) showed high U(eq) as compared with bonded neighbors,
 and therefore the isor command was used.
;

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0849P)²+1.7929P] where P=(Fo²+2Fc²)/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     SHELXL
_refine_ls_extinction_coef       0.0083(10)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_number_reflns         5925
_refine_ls_number_parameters     345
_refine_ls_number_restraints     12
_refine_ls_R_factor_all          0.1638
_refine_ls_R_factor_gt           0.0691
_refine_ls_wR_factor_ref         0.2025
_refine_ls_wR_factor_gt          0.1434
_refine_ls_goodness_of_fit_ref   1.024
_refine_ls_restrained_S_all      1.025
_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_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Cu1 Cu 0.55915(9) 0.05632(4) 0.82591(7) 0.0402(3) Uani 1 1 d . . . . .
Cu2 Cu 0.83531(9) 0.11318(4) 0.96860(7) 0.0397(3) Uani 1 1 d . . . . .
Cl1 Cl 0.3856(2) 0.16783(9) 0.60070(16) 0.0558(5) Uani 1 1 d . . . . .
C1 C 0.8366(8) 0.0587(3) 0.7585(6) 0.0408(16) Uani 1 1 d . . . . .
H1A H 0.9056 0.0266 0.7954 0.049 Uiso 1 1 calc R U . . .
C2 C 0.9326(8) 0.1091(3) 0.7369(6) 0.0506(19) Uani 1 1 d . . . . .
H2A H 0.8657 0.1423 0.7065 0.061 Uiso 1 1 calc R U . . .
H2B H 1.0076 0.1219 0.8043 0.061 Uiso 1 1 calc R U . . .
C3 C 1.0158(9) 0.0914(4) 0.6615(7) 0.061(2) Uani 1 1 d . . . . .
H3A H 1.0901 0.0606 0.6944 0.074 Uiso 1 1 calc R U . . .
H3B H 1.0710 0.1252 0.6482 0.074 Uiso 1 1 calc R U . . .
C4 C 0.9022(10) 0.0689(4) 0.5558(6) 0.058(2) Uani 1 1 d . . . . .
H4A H 0.8345 0.1008 0.5193 0.070 Uiso 1 1 calc R U . . .
H4B H 0.9578 0.0555 0.5103 0.070 Uiso 1 1 calc R U . . .
C5 C 0.8087(9) 0.0188(3) 0.5750(6) 0.0509(19) Uani 1 1 d . . . . .
H5A H 0.8756 -0.0146 0.6039 0.061 Uiso 1 1 calc R U . . .
H5B H 0.7330 0.0068 0.5074 0.061 Uiso 1 1 calc R U . . .
C6 C 0.7270(8) 0.0357(3) 0.6519(5) 0.0394(16) Uani 1 1 d . . . . .
H6A H 0.6550 0.0676 0.6185 0.047 Uiso 1 1 calc R U . . .
C7 C 0.6158(9) -0.0685(3) 0.6210(6) 0.057(2) Uani 1 1 d . . . . .
H7A H 0.6636 -0.0824 0.5748 0.068 Uiso 1 1 calc R U . . .
C8 C 0.5121(10) -0.0991(4) 0.6542(7) 0.062(2) Uani 1 1 d . . . . .
H8A H 0.4759 -0.1374 0.6355 0.074 Uiso 1 1 calc R U . . .
C9 C 0.4740(9) -0.0613(3) 0.7205(6) 0.0515(19) Uani 1 1 d . . . . .
H9A H 0.4059 -0.0702 0.7556 0.062 Uiso 1 1 calc R U . . .
C10 C 0.5271(7) 0.1442(3) 0.9882(5) 0.0390(16) Uani 1 1 d . . . . .
H10A H 0.4932 0.1135 1.0268 0.047 Uiso 1 1 calc R U . . .
C11 C 0.3865(7) 0.1748(3) 0.9100(5) 0.0412(17) Uani 1 1 d . . . . .
H11A H 0.4200 0.2031 0.8680 0.049 Uiso 1 1 calc R U . . .
H11B H 0.3230 0.1455 0.8614 0.049 Uiso 1 1 calc R U . . .
C12 C 0.2905(8) 0.2066(3) 0.9648(6) 0.054(2) Uani 1 1 d . . . . .
H12A H 0.2053 0.2265 0.9116 0.064 Uiso 1 1 calc R U . . .
H12B H 0.2486 0.1782 1.0018 0.064 Uiso 1 1 calc R U . . .
C13 C 0.3868(9) 0.2512(3) 1.0435(7) 0.055(2) Uani 1 1 d . . . . .
H13A H 0.3252 0.2695 1.0807 0.066 Uiso 1 1 calc R U . . .
H13B H 0.4192 0.2819 1.0052 0.066 Uiso 1 1 calc R U . . .
C14 C 0.5279(8) 0.2229(3) 1.1246(6) 0.0473(18) Uani 1 1 d . . . . .
H14A H 0.4959 0.1954 1.1687 0.057 Uiso 1 1 calc R U . . .
H14B H 0.5905 0.2532 1.1709 0.057 Uiso 1 1 calc R U . . .
C15 C 0.6236(7) 0.1899(3) 1.0686(5) 0.0370(16) Uani 1 1 d . . . . .
H15A H 0.6602 0.2192 1.0288 0.044 Uiso 1 1 calc R U . . .
C16 C 0.8074(9) 0.1658(3) 1.2550(6) 0.0496(19) Uani 1 1 d . . . . .
H16A H 0.7542 0.1833 1.2950 0.060 Uiso 1 1 calc R U . . .
C17 C 0.9485(9) 0.1389(4) 1.2954(6) 0.056(2) Uani 1 1 d . . . . .
H17A H 1.0081 0.1337 1.3670 0.068 Uiso 1 1 calc R U . . .
C18 C 0.9829(9) 0.1216(4) 1.2086(6) 0.055(2) Uani 1 1 d . . . . .
H18A H 1.0735 0.1027 1.2120 0.065 Uiso 1 1 calc R U . . .
C19 C 0.7710(12) 0.2370(4) 0.8279(7) 0.083(3) Uani 1 1 d . . . . .
H19A H 0.8055 0.2762 0.8205 0.125 Uiso 1 1 calc R U . . .
H19B H 0.6726 0.2390 0.8366 0.125 Uiso 1 1 calc R U . . .
H19C H 0.7622 0.2144 0.7652 0.125 Uiso 1 1 calc R U . . .
C20 C 0.3154(7) 0.0223(3) 0.9216(6) 0.0409(17) Uani 1 1 d . . . . .
C21 C 0.1374(8) 0.0493(3) 0.9931(6) 0.0418(17) Uani 1 1 d . . . . .
N1 N 0.5471(6) -0.0095(2) 0.7286(5) 0.0409(14) Uani 1 1 d . . . . .
N2 N 0.6353(6) -0.0151(2) 0.6674(4) 0.0386(13) Uani 1 1 d . . . . .
N3 N 0.8687(6) 0.1353(3) 1.1173(5) 0.0436(14) Uani 1 1 d . . . . .
N4 N 0.7598(6) 0.1627(2) 1.1485(4) 0.0401(14) Uani 1 1 d . . . . .
N5 N 0.2419(7) 0.0125(3) 0.9865(5) 0.0565(18) Uani 1 1 d . U . . .
N6 N 0.3874(7) 0.0265(3) 0.8655(5) 0.0482(15) Uani 1 1 d . . . . .
N7 N 0.0434(6) 0.0794(3) 1.0041(5) 0.0463(15) Uani 1 1 d . . . . .
O1 O 0.7575(5) 0.0794(2) 0.8246(3) 0.0400(11) Uani 1 1 d . . . . .
O2 O 0.6157(5) 0.1178(2) 0.9323(4) 0.0417(12) Uani 1 1 d . . . . .
O3 O 0.8809(6) 0.2089(2) 0.9208(5) 0.0634(15) Uani 1 1 d . . . . .
H3 H 0.9277 0.2280 0.9776 0.095 Uiso 1 1 d R U . . .
O4 O 0.5033(8) 0.1816(3) 0.5582(6) 0.094(2) Uani 1 1 d . . . . .
O5 O 0.4128(7) 0.1124(3) 0.6530(5) 0.0782(19) Uani 1 1 d . U . . .
O6 O 0.3809(9) 0.2128(3) 0.6733(5) 0.100(2) Uani 1 1 d . . . . .
O7 O 0.2406(7) 0.1652(3) 0.5148(5) 0.089(2) Uani 1 1 d . . . . .


_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 1.918(4) . ?
Cu1 O2 1.925(4) . ?
Cu1 N1 1.953(5) . ?
Cu1 N6 1.964(7) . ?
Cu1 Cu2 2.9081(12) . ?
Cu2 O2 1.927(4) . ?
Cu2 O1 1.957(4) . ?
Cu2 N3 1.962(6) . ?
Cu2 N7 1.975(6) 1_655 ?
Cu2 O3 2.336(6) . ?
Cl1 O5 1.414(6) . ?
Cl1 O6 1.415(6) . ?
Cl1 O4 1.428(7) . ?
Cl1 O7 1.434(6) . ?
C1 O1 1.409(8) . ?
C1 C6 1.524(9) . ?
C1 C2 1.534(9) . ?
C1 H1A 0.9800 . ?
C2 C3 1.519(10) . ?
C2 H2A 0.9700 . ?
C2 H2B 0.9700 . ?
C3 C4 1.525(11) . ?
C3 H3A 0.9700 . ?
C3 H3B 0.9700 . ?
C4 C5 1.502(11) . ?
C4 H4A 0.9700 . ?
C4 H4B 0.9700 . ?
C5 C6 1.519(9) . ?
C5 H5A 0.9700 . ?
C5 H5B 0.9700 . ?
C6 N2 1.487(8) . ?
C6 H6A 0.9800 . ?
C7 N2 1.340(9) . ?
C7 C8 1.377(11) . ?
C7 H7A 0.9300 . ?
C8 C9 1.363(11) . ?
C8 H8A 0.9300 . ?
C9 N1 1.338(9) . ?
C9 H9A 0.9300 . ?
C10 O2 1.418(7) . ?
C10 C11 1.524(9) . ?
C10 C15 1.535(9) . ?
C10 H10A 0.9800 . ?
C11 C12 1.515(9) . ?
C11 H11A 0.9700 . ?
C11 H11B 0.9700 . ?
C12 C13 1.505(10) . ?
C12 H12A 0.9700 . ?
C12 H12B 0.9700 . ?
C13 C14 1.520(10) . ?
C13 H13A 0.9700 . ?
C13 H13B 0.9700 . ?
C14 C15 1.537(9) . ?
C14 H14A 0.9700 . ?
C14 H14B 0.9700 . ?
C15 N4 1.476(8) . ?
C15 H15A 0.9800 . ?
C16 N4 1.336(9) . ?
C16 C17 1.373(10) . ?
C16 H16A 0.9300 . ?
C17 C18 1.360(11) . ?
C17 H17A 0.9300 . ?
C18 N3 1.344(9) . ?
C18 H18A 0.9300 . ?
C19 O3 1.450(10) . ?
C19 H19A 0.9600 . ?
C19 H19B 0.9600 . ?
C19 H19C 0.9600 . ?
C20 N6 1.166(9) . ?
C20 N5 1.293(9) . ?
C21 N7 1.155(8) . ?
C21 N5 1.303(9) . ?
N1 N2 1.347(7) . ?
N3 N4 1.367(7) . ?
N7 Cu2 1.975(6) 1_455 ?
O3 H3 0.8499 . ?

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 O2 78.05(18) . . ?
O1 Cu1 N1 92.1(2) . . ?
O2 Cu1 N1 168.2(2) . . ?
O1 Cu1 N6 165.0(2) . . ?
O2 Cu1 N6 95.1(2) . . ?
N1 Cu1 N6 93.0(2) . . ?
O1 Cu1 Cu2 41.88(13) . . ?
O2 Cu1 Cu2 41.00(13) . . ?
N1 Cu1 Cu2 127.35(17) . . ?
N6 Cu1 Cu2 126.08(18) . . ?
O2 Cu2 O1 77.09(18) . . ?
O2 Cu2 N3 91.3(2) . . ?
O1 Cu2 N3 165.0(2) . . ?
O2 Cu2 N7 160.3(2) . 1_655 ?
O1 Cu2 N7 94.7(2) . 1_655 ?
N3 Cu2 N7 93.3(2) . 1_655 ?
O2 Cu2 O3 99.0(2) . . ?
O1 Cu2 O3 97.7(2) . . ?
N3 Cu2 O3 93.4(2) . . ?
N7 Cu2 O3 99.8(2) 1_655 . ?
O2 Cu2 Cu1 40.97(13) . . ?
O1 Cu2 Cu1 40.87(12) . . ?
N3 Cu2 Cu1 124.64(17) . . ?
N7 Cu2 Cu1 123.46(18) 1_655 . ?
O3 Cu2 Cu1 115.66(14) . . ?
O5 Cl1 O6 110.1(4) . . ?
O5 Cl1 O4 111.0(4) . . ?
O6 Cl1 O4 108.9(5) . . ?
O5 Cl1 O7 108.3(4) . . ?
O6 Cl1 O7 109.5(4) . . ?
O4 Cl1 O7 109.1(4) . . ?
O1 C1 C6 112.0(5) . . ?
O1 C1 C2 109.4(6) . . ?
C6 C1 C2 108.8(6) . . ?
O1 C1 H1A 108.9 . . ?
C6 C1 H1A 108.9 . . ?
C2 C1 H1A 108.9 . . ?
C3 C2 C1 112.9(7) . . ?
C3 C2 H2A 109.0 . . ?
C1 C2 H2A 109.0 . . ?
C3 C2 H2B 109.0 . . ?
C1 C2 H2B 109.0 . . ?
H2A C2 H2B 107.8 . . ?
C2 C3 C4 110.7(6) . . ?
C2 C3 H3A 109.5 . . ?
C4 C3 H3A 109.5 . . ?
C2 C3 H3B 109.5 . . ?
C4 C3 H3B 109.5 . . ?
H3A C3 H3B 108.1 . . ?
C5 C4 C3 110.4(6) . . ?
C5 C4 H4A 109.6 . . ?
C3 C4 H4A 109.6 . . ?
C5 C4 H4B 109.6 . . ?
C3 C4 H4B 109.6 . . ?
H4A C4 H4B 108.1 . . ?
C4 C5 C6 112.2(6) . . ?
C4 C5 H5A 109.2 . . ?
C6 C5 H5A 109.2 . . ?
C4 C5 H5B 109.2 . . ?
C6 C5 H5B 109.2 . . ?
H5A C5 H5B 107.9 . . ?
N2 C6 C5 110.1(5) . . ?
N2 C6 C1 111.3(5) . . ?
C5 C6 C1 112.8(6) . . ?
N2 C6 H6A 107.5 . . ?
C5 C6 H6A 107.5 . . ?
C1 C6 H6A 107.5 . . ?
N2 C7 C8 107.6(7) . . ?
N2 C7 H7A 126.2 . . ?
C8 C7 H7A 126.2 . . ?
C9 C8 C7 105.0(7) . . ?
C9 C8 H8A 127.5 . . ?
C7 C8 H8A 127.5 . . ?
N1 C9 C8 111.4(7) . . ?
N1 C9 H9A 124.3 . . ?
C8 C9 H9A 124.3 . . ?
O2 C10 C11 110.2(6) . . ?
O2 C10 C15 110.3(5) . . ?
C11 C10 C15 109.0(5) . . ?
O2 C10 H10A 109.1 . . ?
C11 C10 H10A 109.1 . . ?
C15 C10 H10A 109.1 . . ?
C12 C11 C10 113.1(6) . . ?
C12 C11 H11A 109.0 . . ?
C10 C11 H11A 109.0 . . ?
C12 C11 H11B 109.0 . . ?
C10 C11 H11B 109.0 . . ?
H11A C11 H11B 107.8 . . ?
C13 C12 C11 110.4(6) . . ?
C13 C12 H12A 109.6 . . ?
C11 C12 H12A 109.6 . . ?
C13 C12 H12B 109.6 . . ?
C11 C12 H12B 109.6 . . ?
H12A C12 H12B 108.1 . . ?
C12 C13 C14 111.8(6) . . ?
C12 C13 H13A 109.3 . . ?
C14 C13 H13A 109.3 . . ?
C12 C13 H13B 109.3 . . ?
C14 C13 H13B 109.3 . . ?
H13A C13 H13B 107.9 . . ?
C13 C14 C15 111.0(6) . . ?
C13 C14 H14A 109.4 . . ?
C15 C14 H14A 109.4 . . ?
C13 C14 H14B 109.4 . . ?
C15 C14 H14B 109.4 . . ?
H14A C14 H14B 108.0 . . ?
N4 C15 C10 111.6(5) . . ?
N4 C15 C14 110.3(5) . . ?
C10 C15 C14 111.8(5) . . ?
N4 C15 H15A 107.7 . . ?
C10 C15 H15A 107.7 . . ?
C14 C15 H15A 107.7 . . ?
N4 C16 C17 108.1(7) . . ?
N4 C16 H16A 125.9 . . ?
C17 C16 H16A 125.9 . . ?
C18 C17 C16 105.5(7) . . ?
C18 C17 H17A 127.2 . . ?
C16 C17 H17A 127.2 . . ?
N3 C18 C17 111.2(7) . . ?
N3 C18 H18A 124.4 . . ?
C17 C18 H18A 124.4 . . ?
O3 C19 H19A 109.5 . . ?
O3 C19 H19B 109.5 . . ?
H19A C19 H19B 109.5 . . ?
O3 C19 H19C 109.5 . . ?
H19A C19 H19C 109.5 . . ?
H19B C19 H19C 109.5 . . ?
N6 C20 N5 174.2(7) . . ?
N7 C21 N5 175.5(8) . . ?
C9 N1 N2 105.4(6) . . ?
C9 N1 Cu1 129.2(5) . . ?
N2 N1 Cu1 124.6(4) . . ?
C7 N2 N1 110.6(6) . . ?
C7 N2 C6 128.7(6) . . ?
N1 N2 C6 120.6(5) . . ?
C18 N3 N4 105.2(6) . . ?
C18 N3 Cu2 131.0(5) . . ?
N4 N3 Cu2 123.3(4) . . ?
C16 N4 N3 110.0(6) . . ?
C16 N4 C15 129.0(6) . . ?
N3 N4 C15 120.5(5) . . ?
C20 N5 C21 120.9(6) . . ?
C20 N6 Cu1 154.0(6) . . ?
C21 N7 Cu2 156.3(6) . 1_455 ?
C1 O1 Cu1 128.6(4) . . ?
C1 O1 Cu2 130.5(4) . . ?
Cu1 O1 Cu2 97.24(19) . . ?
C10 O2 Cu1 129.2(4) . . ?
C10 O2 Cu2 130.2(4) . . ?
Cu1 O2 Cu2 98.04(19) . . ?
C19 O3 Cu2 120.0(5) . . ?
C19 O3 H3 121.9 . . ?
Cu2 O3 H3 108.3 . . ?

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
O1 C1 C2 C3 -177.1(6) . . . . ?
C6 C1 C2 C3 -54.6(8) . . . . ?
C1 C2 C3 C4 56.8(9) . . . . ?
C2 C3 C4 C5 -55.8(9) . . . . ?
C3 C4 C5 C6 55.4(9) . . . . ?
C4 C5 C6 N2 179.5(6) . . . . ?
C4 C5 C6 C1 -55.5(8) . . . . ?
O1 C1 C6 N2 -61.4(7) . . . . ?
C2 C1 C6 N2 177.5(5) . . . . ?
O1 C1 C6 C5 174.3(6) . . . . ?
C2 C1 C6 C5 53.2(8) . . . . ?
N2 C7 C8 C9 0.0(10) . . . . ?
C7 C8 C9 N1 0.6(10) . . . . ?
O2 C10 C11 C12 -177.2(6) . . . . ?
C15 C10 C11 C12 -55.9(8) . . . . ?
C10 C11 C12 C13 56.9(9) . . . . ?
C11 C12 C13 C14 -55.7(9) . . . . ?
C12 C13 C14 C15 55.3(9) . . . . ?
O2 C10 C15 N4 -60.3(7) . . . . ?
C11 C10 C15 N4 178.5(5) . . . . ?
O2 C10 C15 C14 175.7(6) . . . . ?
C11 C10 C15 C14 54.5(8) . . . . ?
C13 C14 C15 N4 -179.9(6) . . . . ?
C13 C14 C15 C10 -55.1(8) . . . . ?
N4 C16 C17 C18 1.7(9) . . . . ?
C16 C17 C18 N3 -1.4(10) . . . . ?
C8 C9 N1 N2 -0.9(9) . . . . ?
C8 C9 N1 Cu1 -170.6(6) . . . . ?
C8 C7 N2 N1 -0.6(9) . . . . ?
C8 C7 N2 C6 -175.5(7) . . . . ?
C9 N1 N2 C7 1.0(7) . . . . ?
Cu1 N1 N2 C7 171.3(5) . . . . ?
C9 N1 N2 C6 176.3(6) . . . . ?
Cu1 N1 N2 C6 -13.4(8) . . . . ?
C5 C6 N2 C7 -2.4(10) . . . . ?
C1 C6 N2 C7 -128.3(7) . . . . ?
C5 C6 N2 N1 -176.9(6) . . . . ?
C1 C6 N2 N1 57.3(8) . . . . ?
C17 C18 N3 N4 0.5(9) . . . . ?
C17 C18 N3 Cu2 -170.7(6) . . . . ?
C17 C16 N4 N3 -1.4(8) . . . . ?
C17 C16 N4 C15 -173.4(7) . . . . ?
C18 N3 N4 C16 0.6(8) . . . . ?
Cu2 N3 N4 C16 172.6(5) . . . . ?
C18 N3 N4 C15 173.3(6) . . . . ?
Cu2 N3 N4 C15 -14.7(8) . . . . ?
C10 C15 N4 C16 -128.1(7) . . . . ?
C14 C15 N4 C16 -3.2(10) . . . . ?
C10 C15 N4 N3 60.7(8) . . . . ?
C14 C15 N4 N3 -174.4(6) . . . . ?
C6 C1 O1 Cu1 26.3(8) . . . . ?
C2 C1 O1 Cu1 147.0(5) . . . . ?
C6 C1 O1 Cu2 179.7(4) . . . . ?
C2 C1 O1 Cu2 -59.6(7) . . . . ?
C11 C10 O2 Cu1 -61.7(7) . . . . ?
C15 C10 O2 Cu1 177.8(4) . . . . ?
C11 C10 O2 Cu2 140.5(5) . . . . ?
C15 C10 O2 Cu2 20.0(8) . . . . ?

_diffrn_measured_fraction_theta_max 0.991
_diffrn_reflns_theta_full        27.44
_diffrn_measured_fraction_theta_full 0.991
_refine_diff_density_max         0.936
_refine_diff_density_min         -1.165
_refine_diff_density_rms         0.136
_database_code_depnum_ccdc_archive 'CCDC 987105'
#######################################################################
#
#                 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_3

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C14 H22 Cl2 Cu2 N4 O2'
_chemical_formula_weight         476.35

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cu Cu 0.3201 1.2651 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_symmetry_cell_setting           triclinic
_symmetry_space_group_name_H-M   P-1

loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   4.4013(9)
_cell_length_b                   8.2656(17)
_cell_length_c                   12.976(3)
_cell_angle_alpha                82.02(3)
_cell_angle_beta                 87.00(3)
_cell_angle_gamma                79.24(3)
_cell_volume                     459.10(17)
_cell_formula_units_Z            1
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    4106
_cell_measurement_theta_min      3.16
_cell_measurement_theta_max      27.50

_exptl_crystal_description       platelet
_exptl_crystal_colour            green
_exptl_crystal_size_max          0.23
_exptl_crystal_size_mid          0.18
_exptl_crystal_size_min          0.09
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.723
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             242
_exptl_absorpt_coefficient_mu    2.622
_exptl_absorpt_correction_type   empirical
_exptl_absorpt_correction_T_min  0.2988
_exptl_absorpt_correction_T_max  1.0000
_exptl_absorpt_process_details   'ABSCOR; Higashi, 1995'

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      293(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 R-AXIS RAPID IP'
_diffrn_measurement_method       'ω scans'
_diffrn_detector_area_resol_mean 0.77
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            4481
_diffrn_reflns_av_R_equivalents  0.0480
_diffrn_reflns_av_sigmaI/netI    0.0604
_diffrn_reflns_limit_h_min       -5
_diffrn_reflns_limit_h_max       5
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_theta_min         3.16
_diffrn_reflns_theta_max         27.48
_reflns_number_total             2077
_reflns_number_gt                1797
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'crystalstructure 3.6.0 (Rigaku/MSC, 2004)'
_computing_cell_refinement       'crystalstructure 3.6.0 (Rigaku/MSC, 2004)'
_computing_data_reduction        'Crystalstructure 2004'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1997)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    'XP (Sheldrick, 1998)'
_computing_publication_material  'XP (Sheldrick, 1998)'

_refine_special_details          
; 
 Refinement of F² against ALL reflections.  The weighted R-factor wR and 
 goodness of fit S are based on F², conventional R-factors R are based 
 on F, with F set to zero for negative F². The threshold expression of 
 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is 
 not relevant to the choice of reflections for refinement.  R-factors based 
 on F² 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/[σ²(Fo²)+(0.0472P)²+0.1345P] where P=(Fo²+2Fc²)/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         2077
_refine_ls_number_parameters     110
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0447
_refine_ls_R_factor_gt           0.0382
_refine_ls_wR_factor_ref         0.1037
_refine_ls_wR_factor_gt          0.0980
_refine_ls_goodness_of_fit_ref   1.086
_refine_ls_restrained_S_all      1.086
_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 0.94852(8) 0.46201(4) 0.39203(2) 0.03284(15) Uani 1 1 d . . .
Cl1 Cl 0.8979(2) 0.23254(9) 0.33052(7) 0.0487(2) Uani 1 1 d . . .
O1 O 0.8926(5) 0.6408(2) 0.47535(16) 0.0397(5) Uani 1 1 d . . .
N1 N 0.6990(6) 0.7729(3) 0.26365(19) 0.0347(5) Uani 1 1 d . . .
N2 N 0.8862(6) 0.6209(3) 0.26350(18) 0.0348(5) Uani 1 1 d . . .
C1 C 0.7217(7) 0.8039(3) 0.4492(2) 0.0364(6) Uani 1 1 d . . .
H1A H 0.8634 0.8811 0.4319 0.044 Uiso 1 1 calc R . .
H1B H 0.5941 0.8370 0.5086 0.044 Uiso 1 1 calc R . .
C2 C 0.5196(7) 0.8109(4) 0.3581(2) 0.0383(7) Uani 1 1 d . . .
H2A H 0.3807 0.7322 0.3754 0.046 Uiso 1 1 calc R . .
H2B H 0.3945 0.9210 0.3450 0.046 Uiso 1 1 calc R . .
C3 C 0.5258(9) 1.0386(4) 0.1481(3) 0.0484(8) Uani 1 1 d . . .
H3A H 0.5699 1.1062 0.1979 0.073 Uiso 1 1 calc R . .
H3B H 0.3092 1.0337 0.1520 0.073 Uiso 1 1 calc R . .
H3C H 0.5799 1.0861 0.0794 0.073 Uiso 1 1 calc R . .
C4 C 0.7110(7) 0.8663(3) 0.1716(2) 0.0376(6) Uani 1 1 d . . .
C5 C 0.9156(8) 0.7743(4) 0.1090(2) 0.0422(7) Uani 1 1 d . . .
H5A H 0.9723 0.8074 0.0404 0.051 Uiso 1 1 calc R . .
C6 C 1.0226(7) 0.6211(4) 0.1682(2) 0.0365(6) Uani 1 1 d . . .
C7 C 1.2502(9) 0.4783(4) 0.1382(3) 0.0527(9) Uani 1 1 d . . .
H7A H 1.2862 0.3946 0.1938 0.063 Uiso 1 1 d R . .
H7B H 1.1841 0.4452 0.0781 0.063 Uiso 1 1 d R . .
H7C H 1.4475 0.5213 0.1194 0.063 Uiso 1 1 d R . .


_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 1.916(2) 2_766 ?
Cu1 O1 1.922(2) . ?
Cu1 N2 1.971(2) . ?
Cu1 Cl1 2.2093(10) . ?
Cu1 Cu1 3.0297(10) 2_766 ?
O1 C1 1.421(3) . ?
O1 Cu1 1.916(2) 2_766 ?
N1 C4 1.334(4) . ?
N1 N2 1.368(3) . ?
N1 C2 1.462(4) . ?
N2 C6 1.347(4) . ?
C1 C2 1.504(4) . ?
C1 H1A 0.9700 . ?
C1 H1B 0.9700 . ?
C2 H2A 0.9700 . ?
C2 H2B 0.9700 . ?
C3 C4 1.503(4) . ?
C3 H3A 0.9600 . ?
C3 H3B 0.9600 . ?
C3 H3C 0.9600 . ?
C4 C5 1.374(4) . ?
C5 C6 1.400(4) . ?
C5 H5A 0.9300 . ?
C6 C7 1.481(4) . ?
C7 H7A 0.9259 . ?
C7 H7B 0.9386 . ?
C7 H7C 1.0040 . ?

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 75.75(9) 2_766 . ?
O1 Cu1 N2 159.52(10) 2_766 . ?
O1 Cu1 N2 91.06(9) . . ?
O1 Cu1 Cl1 97.30(7) 2_766 . ?
O1 Cu1 Cl1 161.92(8) . . ?
N2 Cu1 Cl1 99.66(8) . . ?
O1 Cu1 Cu1 37.94(6) 2_766 2_766 ?
O1 Cu1 Cu1 37.80(6) . 2_766 ?
N2 Cu1 Cu1 127.17(7) . 2_766 ?
Cl1 Cu1 Cu1 133.11(4) . 2_766 ?
C1 O1 Cu1 128.08(17) . 2_766 ?
C1 O1 Cu1 126.78(18) . . ?
Cu1 O1 Cu1 104.25(9) 2_766 . ?
C4 N1 N2 111.2(2) . . ?
C4 N1 C2 129.6(2) . . ?
N2 N1 C2 119.2(2) . . ?
C6 N2 N1 106.3(2) . . ?
C6 N2 Cu1 132.3(2) . . ?
N1 N2 Cu1 120.96(19) . . ?
O1 C1 C2 110.7(2) . . ?
O1 C1 H1A 109.5 . . ?
C2 C1 H1A 109.5 . . ?
O1 C1 H1B 109.5 . . ?
C2 C1 H1B 109.5 . . ?
H1A C1 H1B 108.1 . . ?
N1 C2 C1 112.4(2) . . ?
N1 C2 H2A 109.1 . . ?
C1 C2 H2A 109.1 . . ?
N1 C2 H2B 109.1 . . ?
C1 C2 H2B 109.1 . . ?
H2A C2 H2B 107.9 . . ?
C4 C3 H3A 109.5 . . ?
C4 C3 H3B 109.5 . . ?
H3A C3 H3B 109.5 . . ?
C4 C3 H3C 109.5 . . ?
H3A C3 H3C 109.5 . . ?
H3B C3 H3C 109.5 . . ?
N1 C4 C5 106.9(2) . . ?
N1 C4 C3 123.2(3) . . ?
C5 C4 C3 129.8(3) . . ?
C4 C5 C6 107.0(3) . . ?
C4 C5 H5A 126.5 . . ?
C6 C5 H5A 126.5 . . ?
N2 C6 C5 108.6(3) . . ?
N2 C6 C7 122.6(3) . . ?
C5 C6 C7 128.9(3) . . ?
C6 C7 H7A 110.7 . . ?
C6 C7 H7B 109.1 . . ?
H7A C7 H7B 114.5 . . ?
C6 C7 H7C 106.0 . . ?
H7A C7 H7C 108.6 . . ?
H7B C7 H7C 107.6 . . ?

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
O1 Cu1 O1 C1 -169.9(3) 2_766 . . . ?
N2 Cu1 O1 C1 26.0(3) . . . . ?
Cl1 Cu1 O1 C1 -100.7(3) . . . . ?
Cu1 Cu1 O1 C1 -169.9(3) 2_766 . . . ?
O1 Cu1 O1 Cu1 0.0 2_766 . . 2_766 ?
N2 Cu1 O1 Cu1 -164.16(12) . . . 2_766 ?
Cl1 Cu1 O1 Cu1 69.2(3) . . . 2_766 ?
C4 N1 N2 C6 0.9(3) . . . . ?
C2 N1 N2 C6 -179.5(3) . . . . ?
C4 N1 N2 Cu1 174.3(2) . . . . ?
C2 N1 N2 Cu1 -6.1(4) . . . . ?
O1 Cu1 N2 C6 92.0(4) 2_766 . . . ?
O1 Cu1 N2 C6 141.1(3) . . . . ?
Cl1 Cu1 N2 C6 -53.5(3) . . . . ?
Cu1 Cu1 N2 C6 129.0(3) 2_766 . . . ?
O1 Cu1 N2 N1 -79.5(3) 2_766 . . . ?
O1 Cu1 N2 N1 -30.4(2) . . . . ?
Cl1 Cu1 N2 N1 135.0(2) . . . . ?
Cu1 Cu1 N2 N1 -42.5(3) 2_766 . . . ?
Cu1 O1 C1 C2 -153.4(2) 2_766 . . . ?
Cu1 O1 C1 C2 14.1(4) . . . . ?
C4 N1 C2 C1 -119.8(3) . . . . ?
N2 N1 C2 C1 60.7(3) . . . . ?
O1 C1 C2 N1 -62.9(3) . . . . ?
N2 N1 C4 C5 -0.9(4) . . . . ?
C2 N1 C4 C5 179.6(3) . . . . ?
N2 N1 C4 C3 179.0(3) . . . . ?
C2 N1 C4 C3 -0.5(5) . . . . ?
N1 C4 C5 C6 0.5(4) . . . . ?
C3 C4 C5 C6 -179.4(3) . . . . ?
N1 N2 C6 C5 -0.6(3) . . . . ?
Cu1 N2 C6 C5 -173.0(2) . . . . ?
N1 N2 C6 C7 178.4(3) . . . . ?
Cu1 N2 C6 C7 6.0(5) . . . . ?
C4 C5 C6 N2 0.1(4) . . . . ?
C4 C5 C6 C7 -178.9(3) . . . . ?

_diffrn_measured_fraction_theta_max 0.986
_diffrn_reflns_theta_full        27.48
_diffrn_measured_fraction_theta_full 0.986
_refine_diff_density_max         0.486
_refine_diff_density_min         -0.844
_refine_diff_density_rms         0.094
_database_code_depnum_ccdc_archive 'CCDC 987106'
#######################################################################
#
#                 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_4

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C18 H22 Cu2 N10 O2'
_chemical_formula_weight         537.54

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)/c

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                   13.095(5)
_cell_length_b                   13.001(5)
_cell_length_c                   13.439(5)
_cell_angle_alpha                90.00
_cell_angle_beta                 106.17(1)
_cell_angle_gamma                90.00
_cell_volume                     2197.3(1)
_cell_formula_units_Z            4
_cell_measurement_temperature    143(2)
_cell_measurement_reflns_used    7159
_cell_measurement_theta_min      2.2531
_cell_measurement_theta_max      29.1270

_exptl_crystal_description       chip
_exptl_crystal_colour            blue
_exptl_crystal_size_max          0.22
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.08
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.625
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1096
_exptl_absorpt_coefficient_mu    1.974
_exptl_absorpt_correction_type   Multi-scan
_exptl_absorpt_correction_T_max  1.0000
_exptl_absorpt_correction_T_min  0.6756
_exptl_absorpt_process_details   'CrystalClear (Rigaku Inc., 2008)'

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      143(2)
_diffrn_radiation_wavelength     0.710747
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'Rotating Anode'
_diffrn_radiation_monochromator  'Graphite Monochromator'
_diffrn_measurement_device_type  'Saturn724+ (2x2 bin mode)'
_diffrn_measurement_method       dtprofit.ref
_diffrn_detector_area_resol_mean 28.5714
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            19000
_diffrn_reflns_av_R_equivalents  0.0765
_diffrn_reflns_av_sigmaI/netI    0.1033
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_h_max       17
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_theta_min         2.22
_diffrn_reflns_theta_max         29.15
_reflns_number_total             5882
_reflns_number_gt                3785
_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    'XP (Sheldrick, 1998)'
_computing_publication_material  'XP (Sheldrick, 1998)'

_refine_special_details          
; 
 Refinement of F² against ALL reflections.  The weighted R-factor wR and 
 goodness of fit S are based on F², conventional R-factors R are based 
 on F, with F set to zero for negative F². The threshold expression of 
 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is 
 not relevant to the choice of reflections for refinement.  R-factors based 
 on F² 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/[σ²(Fo²)+(0.0852P)²+0.0000P] where P=(Fo²+2Fc²)/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         5882
_refine_ls_number_parameters     289
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0996
_refine_ls_R_factor_gt           0.0668
_refine_ls_wR_factor_ref         0.1844
_refine_ls_wR_factor_gt          0.1691
_refine_ls_goodness_of_fit_ref   1.008
_refine_ls_restrained_S_all      1.008
_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 0.40066(5) 0.95863(4) 0.02355(4) 0.01989(17) Uani 1 1 d . . .
Cu2 Cu 0.38229(5) 0.50513(5) -0.05649(4) 0.02185(17) Uani 1 1 d . . .
O2 O 0.5535(3) 0.9402(2) 0.0623(3) 0.0232(7) Uani 1 1 d . . .
O1 O 0.4841(3) 0.5537(3) 0.0668(3) 0.0248(7) Uani 1 1 d . . .
C19 C 0.0768(4) 1.0371(4) -0.0778(4) 0.0263(11) Uani 1 1 d . . .
H19A H 0.0041 1.0241 -0.0982 0.032 Uiso 1 1 calc R . .
N9 N 0.2596(3) 0.5551(3) -0.0093(3) 0.0243(9) Uani 1 1 d . . .
N8 N 0.3872(3) 0.8865(3) 0.1510(3) 0.0246(9) Uani 1 1 d . . .
N7 N 0.3772(4) 0.8200(3) -0.0886(3) 0.0286(10) Uani 1 1 d . . .
N10 N 0.2970(3) 0.4301(3) -0.1770(3) 0.0291(10) Uani 1 1 d . . .
C25 C 0.3840(4) 0.7457(4) -0.1310(4) 0.0223(10) Uani 1 1 d . . .
C14 C 0.3891(4) 0.8620(4) 0.2335(4) 0.0235(10) Uani 1 1 d . . .
C13 C 0.1688(4) 0.5723(4) 0.1080(4) 0.0241(10) Uani 1 1 d . . .
N6 N 0.3919(4) 0.6536(3) -0.1701(3) 0.0325(11) Uani 1 1 d . . .
N5 N 0.2322(3) 1.1136(3) -0.0470(3) 0.0223(8) Uani 1 1 d . . .
N4 N 0.2641(3) 0.5518(3) 0.0940(3) 0.0244(9) Uani 1 1 d . . .
C12 C 0.1574(4) 0.9664(4) -0.0354(4) 0.0246(10) Uani 1 1 d . . .
C11 C 0.1258(4) 1.1297(4) -0.0837(4) 0.0216(10) Uani 1 1 d . . .
C10 C 0.1012(4) 0.5938(4) 0.0111(4) 0.0264(11) Uani 1 1 d . . .
H10A H 0.0299 0.6122 -0.0040 0.032 Uiso 1 1 calc R . .
C9 C 0.3633(4) 0.5221(4) 0.1702(4) 0.0274(11) Uani 1 1 d . . .
H9A H 0.3764 0.4496 0.1625 0.033 Uiso 1 1 calc R . .
H9B H 0.3561 0.5327 0.2394 0.033 Uiso 1 1 calc R . .
C8 C 0.0798(4) 1.2324(4) -0.1226(4) 0.0289(11) Uani 1 1 d . . .
H8A H 0.1363 1.2812 -0.1160 0.043 Uiso 1 1 calc R . .
H8B H 0.0336 1.2551 -0.0827 0.043 Uiso 1 1 calc R . .
H8C H 0.0401 1.2266 -0.1942 0.043 Uiso 1 1 calc R . .
N3 N 0.2531(3) 1.0118(3) -0.0162(3) 0.0227(9) Uani 1 1 d . . .
C7 C 0.3194(4) 1.1851(4) -0.0332(4) 0.0249(10) Uani 1 1 d . . .
H7A H 0.3587 1.1876 0.0395 0.030 Uiso 1 1 calc R . .
H7B H 0.2915 1.2533 -0.0537 0.030 Uiso 1 1 calc R . .
C6 C 0.1464(4) 0.8557(4) -0.0113(5) 0.0332(12) Uani 1 1 d . . .
H6C H 0.2156 0.8262 0.0170 0.050 Uiso 1 1 calc R . .
H6D H 0.1103 0.8198 -0.0737 0.050 Uiso 1 1 calc R . .
H6E H 0.1061 0.8497 0.0381 0.050 Uiso 1 1 calc R . .
C5 C 0.1221(5) 0.5990(5) -0.1736(4) 0.0436(15) Uani 1 1 d . . .
H5A H 0.1792 0.5862 -0.2038 0.065 Uiso 1 1 calc R . .
H5B H 0.0982 0.6688 -0.1874 0.065 Uiso 1 1 calc R . .
H5C H 0.0644 0.5529 -0.2029 0.065 Uiso 1 1 calc R . .
N2 N 0.1755(5) 0.1705(4) -0.3803(5) 0.0585(17) Uani 1 1 d . . .
C4 C 0.2422(5) 0.3883(4) -0.2457(4) 0.0320(12) Uani 1 1 d . . .
C3 C 0.1605(4) 0.5825(4) -0.0589(4) 0.0267(11) Uani 1 1 d . . .
N1 N 0.1723(4) 0.3511(4) -0.3271(4) 0.0472(14) Uani 1 1 d . . .
C2 C 0.1482(5) 0.5696(5) 0.2114(4) 0.0355(13) Uani 1 1 d . . .
H2A H 0.2126 0.5522 0.2633 0.053 Uiso 1 1 calc R . .
H2B H 0.0948 0.5190 0.2111 0.053 Uiso 1 1 calc R . .
H2C H 0.1240 0.6360 0.2265 0.053 Uiso 1 1 calc R . .
C1 C 0.1791(5) 0.2540(4) -0.3520(4) 0.0337(13) Uani 1 1 d . . .
C16 C 0.6057(4) 0.8457(4) 0.0969(4) 0.0246(10) Uani 1 1 d . . .
H16A H 0.5529 0.7921 0.0919 0.030 Uiso 1 1 calc R . .
H16B H 0.6458 0.8521 0.1691 0.030 Uiso 1 1 calc R . .
C17 C 0.4565(4) 0.5837(4) 0.1576(4) 0.0254(10) Uani 1 1 d . . .
H17A H 0.4386 0.6563 0.1534 0.030 Uiso 1 1 calc R . .
H17B H 0.5170 0.5734 0.2176 0.030 Uiso 1 1 calc R . .


_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 O2 1.938(3) . ?
Cu1 O2 1.951(3) 3_675 ?
Cu1 N3 1.981(4) . ?
Cu1 N8 2.003(4) . ?
Cu1 N7 2.314(4) . ?
Cu1 Cu1 3.0404(11) 3_675 ?
Cu2 O1 1.922(3) . ?
Cu2 O1 1.950(3) 3_665 ?
Cu2 N10 1.953(4) . ?
Cu2 N9 1.994(4) . ?
Cu2 Cu2 3.0364(12) 3_665 ?
O2 C16 1.420(5) . ?
O2 Cu1 1.951(3) 3_675 ?
O1 C17 1.419(5) . ?
O1 Cu2 1.950(3) 3_665 ?
C19 C11 1.377(7) . ?
C19 C12 1.396(7) . ?
N9 C3 1.332(6) . ?
N9 N4 1.372(5) . ?
N8 C14 1.146(6) . ?
N7 C25 1.137(6) . ?
N10 C4 1.138(7) . ?
C25 N6 1.323(6) . ?
C14 N6 1.303(6) 4_576 ?
C13 N4 1.341(6) . ?
C13 C10 1.384(7) . ?
C13 C2 1.487(7) . ?
N6 C14 1.303(6) 4_575 ?
N5 C11 1.358(6) . ?
N5 N3 1.390(5) . ?
N5 C7 1.444(6) . ?
N4 C9 1.464(6) . ?
C12 N3 1.343(6) . ?
C12 C6 1.491(7) . ?
C11 C8 1.497(7) . ?
C10 C3 1.385(7) . ?
C9 C17 1.508(7) . ?
C7 C16 1.524(7) 3_675 ?
C5 C3 1.497(7) . ?
N2 C1 1.146(7) . ?
C4 N1 1.308(7) . ?
N1 C1 1.315(7) . ?
C16 C7 1.524(7) 3_675 ?

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
O2 Cu1 O2 77.13(15) . 3_675 ?
O2 Cu1 N3 166.62(15) . . ?
O2 Cu1 N3 92.44(15) 3_675 . ?
O2 Cu1 N8 92.44(15) . . ?
O2 Cu1 N8 159.38(17) 3_675 . ?
N3 Cu1 N8 94.76(17) . . ?
O2 Cu1 N7 91.05(15) . . ?
O2 Cu1 N7 98.45(15) 3_675 . ?
N3 Cu1 N7 98.85(16) . . ?
N8 Cu1 N7 99.49(17) . . ?
O2 Cu1 Cu1 38.72(9) . 3_675 ?
O2 Cu1 Cu1 38.41(10) 3_675 3_675 ?
N3 Cu1 Cu1 130.34(12) . 3_675 ?
N8 Cu1 Cu1 128.88(13) . 3_675 ?
N7 Cu1 Cu1 96.08(11) . 3_675 ?
O1 Cu2 O1 76.70(15) . 3_665 ?
O1 Cu2 N10 168.14(17) . . ?
O1 Cu2 N10 93.56(17) 3_665 . ?
O1 Cu2 N9 92.60(16) . . ?
O1 Cu2 N9 165.78(15) 3_665 . ?
N10 Cu2 N9 95.80(18) . . ?
O1 Cu2 Cu2 38.68(10) . 3_665 ?
O1 Cu2 Cu2 38.02(10) 3_665 3_665 ?
N10 Cu2 Cu2 131.24(13) . 3_665 ?
N9 Cu2 Cu2 130.64(12) . 3_665 ?
C16 O2 Cu1 124.2(3) . . ?
C16 O2 Cu1 125.3(3) . 3_675 ?
Cu1 O2 Cu1 102.87(15) . 3_675 ?
C17 O1 Cu2 123.3(3) . . ?
C17 O1 Cu2 128.1(3) . 3_665 ?
Cu2 O1 Cu2 103.30(15) . 3_665 ?
C11 C19 C12 106.7(4) . . ?
C3 N9 N4 106.1(4) . . ?
C3 N9 Cu2 133.4(3) . . ?
N4 N9 Cu2 120.0(3) . . ?
C14 N8 Cu1 166.7(4) . . ?
C25 N7 Cu1 166.6(4) . . ?
C4 N10 Cu2 176.0(5) . . ?
N7 C25 N6 173.2(5) . . ?
N8 C14 N6 172.9(6) . 4_576 ?
N4 C13 C10 106.5(4) . . ?
N4 C13 C2 123.0(5) . . ?
C10 C13 C2 130.4(5) . . ?
C14 N6 C25 123.6(5) 4_575 . ?
C11 N5 N3 110.6(4) . . ?
C11 N5 C7 129.9(4) . . ?
N3 N5 C7 119.4(4) . . ?
C13 N4 N9 110.9(4) . . ?
C13 N4 C9 129.2(4) . . ?
N9 N4 C9 119.8(4) . . ?
N3 C12 C19 110.3(4) . . ?
N3 C12 C6 121.6(5) . . ?
C19 C12 C6 128.0(5) . . ?
N5 C11 C19 106.9(4) . . ?
N5 C11 C8 122.4(4) . . ?
C19 C11 C8 130.7(5) . . ?
C13 C10 C3 106.6(4) . . ?
N4 C9 C17 111.6(4) . . ?
C12 N3 N5 105.4(4) . . ?
C12 N3 Cu1 133.3(3) . . ?
N5 N3 Cu1 120.6(3) . . ?
N5 C7 C16 111.6(4) . 3_675 ?
N10 C4 N1 172.7(6) . . ?
N9 C3 C10 109.9(4) . . ?
N9 C3 C5 123.7(5) . . ?
C10 C3 C5 126.4(5) . . ?
C4 N1 C1 119.1(5) . . ?
N2 C1 N1 173.4(7) . . ?
O2 C16 C7 111.7(4) . 3_675 ?
O1 C17 C9 111.1(4) . . ?

_diffrn_measured_fraction_theta_max 0.995
_diffrn_reflns_theta_full        29.15
_diffrn_measured_fraction_theta_full 0.995
_refine_diff_density_max         1.676
_refine_diff_density_min         -0.884
_refine_diff_density_rms         0.186

#===End
_database_code_depnum_ccdc_archive 'CCDC 987107'
