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


data_global
_journal_name_full               CrystEngComm
_journal_coden_cambridge         1350
_journal_year                    ?
_journal_volume                  ?
_journal_page_first              ?
loop_
_publ_author_name
'Li Tian'
'Zhi Chen'
'Ao Yu'
'Hai Song'
'Peng Cheng'
_publ_contact_author_name        'Dr Li Tian'
_publ_contact_author_email       lilytianli@hotmail.com

#===END

data_4
_database_code_depnum_ccdc_archive 'CCDC 800364'
#TrackingRef '- compound 1 to 4.cif'

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C16 H28 Cl2 Cu N12 O10'
_chemical_formula_weight         682.95

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           orthorhombic
_symmetry_space_group_name_H-M   'F d d d'

loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x+1/4, -y+1/4, z'
'x, -y+1/4, -z+1/4'
'-x+1/4, y, -z+1/4'
'x, y+1/2, z+1/2'
'-x+1/4, -y+3/4, z+1/2'
'x, -y+3/4, -z+3/4'
'-x+1/4, y+1/2, -z+3/4'
'x+1/2, y, z+1/2'
'-x+3/4, -y+1/4, z+1/2'
'x+1/2, -y+1/4, -z+3/4'
'-x+3/4, y, -z+3/4'
'x+1/2, y+1/2, z'
'-x+3/4, -y+3/4, z'
'x+1/2, -y+3/4, -z+1/4'
'-x+3/4, y+1/2, -z+1/4'
'-x, -y, -z'
'x-1/4, y-1/4, -z'
'-x, y-1/4, z-1/4'
'x-1/4, -y, z-1/4'
'-x, -y+1/2, -z+1/2'
'x-1/4, y+1/4, -z+1/2'
'-x, y+1/4, z+1/4'
'x-1/4, -y+1/2, z+1/4'
'-x+1/2, -y, -z+1/2'
'x+1/4, y-1/4, -z+1/2'
'-x+1/2, y-1/4, z+1/4'
'x+1/4, -y, z+1/4'
'-x+1/2, -y+1/2, -z'
'x+1/4, y+1/4, -z'
'-x+1/2, y+1/4, z-1/4'
'x+1/4, -y+1/2, z-1/4'

_cell_length_a                   25.054(2)
_cell_length_b                   13.2154(9)
_cell_length_c                   17.3885(13)
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_volume                     5757.3(7)
_cell_formula_units_Z            8
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    1851
_cell_measurement_theta_min      2.8472
_cell_measurement_theta_max      29.2137

_exptl_crystal_description       block
_exptl_crystal_colour            blue
_exptl_crystal_size_max          0.20
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.20
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.576
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             2807
_exptl_absorpt_coefficient_mu    1.014
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.8229
_exptl_absorpt_correction_T_max  0.8229
_exptl_absorpt_process_details   ?

_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  ?
_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            3454
_diffrn_reflns_av_R_equivalents  0.0398
_diffrn_reflns_av_sigmaI/netI    0.0407
_diffrn_reflns_limit_h_min       -27
_diffrn_reflns_limit_h_max       29
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_theta_min         2.85
_diffrn_reflns_theta_max         25.01
_reflns_number_total             1272
_reflns_number_gt                1018
_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. It should be noted oxygen
atoms of ClO~4~^ C^ in the compoud were treated by disorder and these
atoms were refined anisotropically with application of restrains on
interatomic distances and thermal parameters (DFIX, ISOR and SADI
instructions in SHELXL). The detail restrains used in the refinement
are as follow:
DFIX 1.44 0.01 Cl1 O4_$1 Cl1 O4 O3_$1 Cl1 O3 Cl1 Cl1 O5_$1 Cl1 O5 Cl1 O2
DFIX 2.35 O4_$1 O3_$1 O4 O3 O4_$1 O5_$1 O4 O5 O5 O3_$1 O5 O3
DFIX 2.35 O4_$1 O2 O4 O2 O3_$1 O2 O3 O2 O5_$1 O2 O5 O2
SADI 0.01 O5 Cl1 O3 Cl1 O4 Cl1
SADI 0.01 O5 O3 O5 O2 O4 O2 O4 O5 O4 O3 O3 O2
SADI 0.01 O5_$1 Cl1 O2 Cl1 O3_$1 Cl1 O4_$1 Cl1
SADI 0.01 O5_$1 O3_$1 O5_$1 O2 O4_$1 O2 O4_$1 O5_$1 O4_$1 O3_$1 O3_$1 O2
ISOR 0.005 0.01 O2 O3 O4 O5
;

_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^)+(0.1132P)^2^+42.0785P] 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     SHELXL
_refine_ls_extinction_coef       0.0006(4)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^
_refine_ls_number_reflns         1272
_refine_ls_number_parameters     114
_refine_ls_number_restraints     82
_refine_ls_R_factor_all          0.0713
_refine_ls_R_factor_gt           0.0616
_refine_ls_wR_factor_ref         0.1874
_refine_ls_wR_factor_gt          0.1807
_refine_ls_goodness_of_fit_ref   1.073
_refine_ls_restrained_S_all      2.330
_refine_ls_shift/su_max          0.026
_refine_ls_shift/su_mean         0.003

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 0.1250 0.6250 0.1250 0.0206(10) Uani 1 4 d S . .
O1 O 0.1250 0.6250 0.2634(5) 0.032(2) Uani 1 2 d S . .
H1A H 0.1266 0.5742 0.2935 0.039 Uiso 0.50 1 d PR . .
H1B H 0.0930 0.6452 0.2552 0.039 Uiso 0.50 1 d PR . .
N2 N 0.0039(3) 0.4200(6) 0.1680(5) 0.031(2) Uani 1 1 d . . .
N3 N 0.0190(5) 0.3822(7) 0.0990(5) 0.049(3) Uani 1 1 d . . .
N1 N 0.0679(3) 0.5173(6) 0.1294(4) 0.0252(19) Uani 1 1 d . . .
C1 C 0.0337(4) 0.5002(7) 0.1852(6) 0.026(2) Uani 1 1 d . . .
H1 H 0.0307 0.5384 0.2298 0.032 Uiso 1 1 calc R . .
C2 C 0.0572(5) 0.4435(9) 0.0784(6) 0.046(3) Uani 1 1 d . . .
H2 H 0.0756 0.4367 0.0322 0.055 Uiso 1 1 calc R . .
C3 C -0.0373(4) 0.3706(8) 0.2144(7) 0.038(3) Uani 1 1 d . . .
H3A H -0.0625 0.3374 0.1804 0.046 Uiso 1 1 calc R . .
H3B H -0.0565 0.4217 0.2433 0.046 Uiso 1 1 calc R . .
C4 C -0.0146(5) 0.2933(8) 0.2698(6) 0.038(3) Uani 1 1 d . . .
H4A H -0.0435 0.2656 0.3004 0.045 Uiso 1 1 calc R . .
H4B H 0.0099 0.3270 0.3045 0.045 Uiso 1 1 calc R . .
Cl1 Cl 0.13145(14) 0.3750 0.3750 0.0381(12) Uani 1 2 d SD . .
O3 O 0.1031(5) 0.4357(11) 0.3226(7) 0.039(4) Uani 0.50 1 d PDU A -1
O2 O 0.1864(4) 0.3750(11) 0.3750(9) 0.127(8) Uani 1 2 d SDU A -1
O5 O 0.1213(6) 0.4319(15) 0.4513(7) 0.088(7) Uani 0.50 1 d PDU A -1
O4 O 0.1078(6) 0.2797(9) 0.3873(13) 0.117(11) Uani 0.50 1 d PDU A -1

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 0.0251(15) 0.0136(13) 0.0232(14) 0.000 0.000 0.000
O1 0.047(6) 0.029(5) 0.022(5) 0.000 0.000 0.004(5)
N2 0.034(5) 0.026(4) 0.034(5) 0.006(4) -0.003(4) -0.007(4)
N3 0.076(7) 0.039(6) 0.031(5) -0.008(4) 0.005(5) -0.031(6)
N1 0.033(4) 0.019(4) 0.023(4) -0.001(3) 0.001(3) -0.006(4)
C1 0.028(5) 0.021(5) 0.030(5) 0.001(4) -0.002(4) 0.001(4)
C2 0.067(8) 0.039(6) 0.030(5) -0.010(5) 0.015(6) -0.028(6)
C3 0.029(5) 0.038(6) 0.046(6) 0.009(5) 0.005(5) -0.009(5)
C4 0.037(6) 0.036(6) 0.040(6) 0.008(5) 0.007(5) -0.009(5)
Cl1 0.032(2) 0.034(2) 0.048(2) 0.0196(17) 0.000 0.000
O3 0.039(8) 0.039(8) 0.040(8) 0.022(8) -0.007(7) 0.007(7)
O2 0.063(10) 0.182(18) 0.137(15) 0.000(13) 0.00(2) 0.00(2)
O5 0.099(14) 0.097(15) 0.068(12) -0.022(11) -0.007(10) 0.046(12)
O4 0.16(2) 0.087(17) 0.108(17) 0.047(14) -0.068(15) -0.034(15)

_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 2.019(8) 3_565 ?
Cu1 N1 2.019(8) . ?
Cu1 N1 2.019(8) 2_565 ?
Cu1 N1 2.019(8) 4 ?
Cu1 O1 2.406(9) 3_565 ?
Cu1 O1 2.406(9) . ?
O1 H1A 0.8527 . ?
O1 H1B 0.8564 . ?
N2 C1 1.330(12) . ?
N2 N3 1.354(13) . ?
N2 C3 1.462(13) . ?
N3 C2 1.305(15) . ?
N1 C1 1.314(12) . ?
N1 C2 1.345(13) . ?
C1 H1 0.9300 . ?
C2 H2 0.9300 . ?
C3 C4 1.515(15) . ?
C3 H3A 0.9700 . ?
C3 H3B 0.9700 . ?
C4 C4 1.52(2) 21 ?
C4 H4A 0.9700 . ?
C4 H4B 0.9700 . ?
Cl1 O2 1.377(10) . ?
Cl1 O3 1.406(8) . ?
Cl1 O3 1.406(8) 7 ?
Cl1 O4 1.408(9) . ?
Cl1 O4 1.408(8) 7 ?
Cl1 O5 1.546(8) 7 ?
Cl1 O5 1.546(8) . ?

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 89.8(5) 3_565 . ?
N1 Cu1 N1 90.3(5) 3_565 2_565 ?
N1 Cu1 N1 175.6(4) . 2_565 ?
N1 Cu1 N1 175.6(4) 3_565 4 ?
N1 Cu1 N1 90.3(5) . 4 ?
N1 Cu1 N1 89.8(5) 2_565 4 ?
N1 Cu1 O1 87.8(2) 3_565 3_565 ?
N1 Cu1 O1 92.2(2) . 3_565 ?
N1 Cu1 O1 92.2(2) 2_565 3_565 ?
N1 Cu1 O1 87.8(2) 4 3_565 ?
N1 Cu1 O1 92.2(2) 3_565 . ?
N1 Cu1 O1 87.8(2) . . ?
N1 Cu1 O1 87.8(2) 2_565 . ?
N1 Cu1 O1 92.2(2) 4 . ?
O1 Cu1 O1 180.000(1) 3_565 . ?
Cu1 O1 H1A 127.9 . . ?
Cu1 O1 H1B 80.4 . . ?
H1A O1 H1B 113.0 . . ?
C1 N2 N3 109.6(8) . . ?
C1 N2 C3 128.9(9) . . ?
N3 N2 C3 121.4(9) . . ?
C2 N3 N2 102.6(8) . . ?
C1 N1 C2 103.4(8) . . ?
C1 N1 Cu1 127.7(6) . . ?
C2 N1 Cu1 128.8(7) . . ?
N1 C1 N2 109.8(9) . . ?
N1 C1 H1 125.1 . . ?
N2 C1 H1 125.1 . . ?
N3 C2 N1 114.6(9) . . ?
N3 C2 H2 122.7 . . ?
N1 C2 H2 122.7 . . ?
N2 C3 C4 112.8(9) . . ?
N2 C3 H3A 109.0 . . ?
C4 C3 H3A 109.0 . . ?
N2 C3 H3B 109.0 . . ?
C4 C3 H3B 109.0 . . ?
H3A C3 H3B 107.8 . . ?
C3 C4 C4 113.5(12) . 21 ?
C3 C4 H4A 108.9 . . ?
C4 C4 H4A 108.9 21 . ?
C3 C4 H4B 108.9 . . ?
C4 C4 H4B 108.9 21 . ?
H4A C4 H4B 107.7 . . ?
O2 Cl1 O3 120.3(9) . . ?
O2 Cl1 O3 120.3(9) . 7 ?
O3 Cl1 O3 119.4(11) . 7 ?
O2 Cl1 O4 114.9(10) . . ?
O3 Cl1 O4 113.4(7) . . ?
O3 Cl1 O4 34.8(9) 7 . ?
O2 Cl1 O4 114.9(10) . 7 ?
O3 Cl1 O4 34.8(9) . 7 ?
O3 Cl1 O4 113.4(7) 7 7 ?
O4 Cl1 O4 130.2(15) . 7 ?
O2 Cl1 O5 99.5(8) . 7 ?
O3 Cl1 O5 68.8(8) . 7 ?
O3 Cl1 O5 101.3(6) 7 7 ?
O4 Cl1 O5 68.0(8) . 7 ?
O4 Cl1 O5 103.6(7) 7 7 ?
O2 Cl1 O5 99.5(8) . . ?
O3 Cl1 O5 101.3(6) . . ?
O3 Cl1 O5 68.8(8) 7 . ?
O4 Cl1 O5 103.6(7) . . ?
O4 Cl1 O5 68.0(8) 7 . ?
O5 Cl1 O5 161.0(11) 7 . ?

_diffrn_measured_fraction_theta_max 0.999
_diffrn_reflns_theta_full        25.01
_diffrn_measured_fraction_theta_full 0.999
_refine_diff_density_max         0.816
_refine_diff_density_min         -0.877
_refine_diff_density_rms         0.111

#===


# Attachment '- compound 1 to 4.cif'

data_1
_database_code_depnum_ccdc_archive 'CCDC 842057'
#TrackingRef '- compound 1 to 4.cif'

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C10 H12 Cl2 Cu N12 O8'
_chemical_formula_weight         562.77

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/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                   9.1844(7)
_cell_length_b                   13.1362(14)
_cell_length_c                   8.2785(7)
_cell_angle_alpha                90.00
_cell_angle_beta                 95.885(7)
_cell_angle_gamma                90.00
_cell_volume                     993.52(15)
_cell_formula_units_Z            2
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    1079
_cell_measurement_theta_min      2.4655
_cell_measurement_theta_max      29.1275

_exptl_crystal_description       block
_exptl_crystal_colour            blue
_exptl_crystal_size_max          0.10
_exptl_crystal_size_mid          0.10
_exptl_crystal_size_min          0.10
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.881
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             566
_exptl_absorpt_coefficient_mu    1.440
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.8694
_exptl_absorpt_correction_T_max  0.8694
_exptl_absorpt_process_details   
;
CrysAlisPro, Oxford Diffraction Ltd.,
Version 1.171.33.41 (release 06-05-2009 CrysAlis171 .NET)
(compiled May 6 2009,17:20:42)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;

_exptl_special_details           
;
?
;

_diffrn_ambient_temperature      293(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'SuperNova (Mo) X-ray Source'
_diffrn_radiation_monochromator  mirror
_diffrn_measurement_device_type  'SuperNova, Single source at offset), Eos'
_diffrn_measurement_method       '\w scans'
_diffrn_detector_area_resol_mean 16.2116
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            1886
_diffrn_reflns_av_R_equivalents  0.0282
_diffrn_reflns_av_sigmaI/netI    0.0509
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_l_min       -9
_diffrn_reflns_limit_l_max       9
_diffrn_reflns_theta_min         2.47
_diffrn_reflns_theta_max         25.01
_reflns_number_total             921
_reflns_number_gt                734
_reflns_threshold_expression     >2sigma(I)

_computing_cell_refinement       
;
CrysAlisPro, Oxford Diffraction Ltd.,
Version 1.171.33.41 (release 06-05-2009 CrysAlis171 .NET)
(compiled May 6 2009,17:20:42)
;
_computing_data_collection       
;
CrysAlisPro, Oxford Diffraction Ltd.,
Version 1.171.33.41 (release 06-05-2009 CrysAlis171 .NET)
(compiled May 6 2009,17:20:42)
;
_computing_data_reduction        
;
CrysAlisPro, Oxford Diffraction Ltd.,
Version 1.171.33.41 (release 06-05-2009 CrysAlis171 .NET)
(compiled May 6 2009,17:20:42)
;
_computing_molecular_graphics    
;
O. V. Dolomanov, L. J. Bourhis, R. J. Gildea, J. A. K. Howard and H. Puschmann,
OLEX2: a complete structure solution, refinement and analysis program.
J. Appl. Cryst. (2009). 42, 339-341.
;
_computing_publication_material  
;
O. V. Dolomanov, L. J. Bourhis, R. J. Gildea, J. A. K. Howard and H. Puschmann,
OLEX2: a complete structure solution, refinement and analysis program.
J. Appl. Cryst. (2009). 42, 339-341.
;
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'

_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. It should be noted O1 and O3
atoms of ClO~4~^ C^ in the compoud were treated by disorder and these
atoms were refined anisotropically with application of restrains on thermal
parameters (ISOR and EADP instructions in SHELXL).
;

_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^)+(0.0579P)^2^+0.9155P] 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         921
_refine_ls_number_parameters     92
_refine_ls_number_restraints     12
_refine_ls_R_factor_all          0.0563
_refine_ls_R_factor_gt           0.0417
_refine_ls_wR_factor_ref         0.1062
_refine_ls_wR_factor_gt          0.1021
_refine_ls_goodness_of_fit_ref   1.048
_refine_ls_restrained_S_all      1.043
_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 1.0000 0.0000 0.5000 0.0151(3) Uani 1 4 d S . .
C1 C 1.1925(5) 0.1299(5) 0.3035(6) 0.0566(17) Uani 1 1 d . . .
H1 H 1.2781 0.1044 0.3587 0.068 Uiso 1 1 calc R . .
C2 C 0.9699(4) 0.1568(3) 0.2359(4) 0.0193(8) Uani 1 1 d . . .
H2 H 0.8682 0.1558 0.2285 0.023 Uiso 1 1 calc R . .
C3 C 1.0000 0.2725(5) 0.0000 0.0244(13) Uani 1 2 d S . .
H3A H 0.9199 0.3159 0.0253 0.029 Uiso 0.50 1 calc PR . .
H3B H 1.0801 0.3159 -0.0253 0.029 Uiso 0.50 1 calc PR . .
N1 N 1.0565(3) 0.1056(3) 0.3443(4) 0.0206(8) Uani 1 1 d . . .
N2 N 1.0473(3) 0.2094(2) 0.1395(4) 0.0208(8) Uani 1 1 d . . .
N3 N 1.1919(4) 0.1922(4) 0.1796(5) 0.0579(15) Uani 1 1 d . . .
Cl1 Cl 0.62922(12) 0.0000 0.27177(15) 0.0186(4) Uani 1 2 d S . .
O2 O 0.6817(4) 0.0000 0.1149(5) 0.0402(12) Uani 1 2 d S . .
O3B O 0.7471(15) -0.013(2) 0.3973(18) 0.0148(19) Uani 0.230(3) 1 d PU . 2
O1A O 0.5096(7) 0.0646(6) 0.2828(8) 0.0409(13) Uani 0.540(6) 1 d P . 1
O1B O 0.5872(8) 0.1067(7) 0.3049(9) 0.0409(13) Uani 0.460(6) 1 d P . 2
O3A O 0.7447(15) 0.0364(15) 0.3908(18) 0.0148(19) Uani 0.270(3) 1 d PU . 1

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 0.0123(5) 0.0258(6) 0.0075(5) 0.000 0.0025(3) 0.000
C1 0.022(2) 0.096(5) 0.054(3) 0.044(3) 0.015(2) 0.004(3)
C2 0.0225(19) 0.018(2) 0.019(2) -0.0016(17) 0.0072(16) -0.0058(17)
C3 0.032(3) 0.027(3) 0.016(3) 0.000 0.012(2) 0.000
N1 0.0163(15) 0.029(2) 0.0171(16) 0.0000(15) 0.0072(12) -0.0034(14)
N2 0.0247(16) 0.0262(19) 0.0133(17) -0.0007(14) 0.0099(13) -0.0011(15)
N3 0.022(2) 0.092(4) 0.063(3) 0.048(3) 0.0192(19) 0.008(2)
Cl1 0.0137(6) 0.0254(8) 0.0159(7) 0.000 -0.0027(5) 0.000
O2 0.037(2) 0.068(3) 0.016(2) 0.000 0.0027(18) 0.000
O3B 0.0130(19) 0.014(5) 0.016(2) 0.002(3) -0.0054(16) -0.001(3)
O1A 0.034(3) 0.048(4) 0.039(3) 0.002(3) -0.003(3) 0.019(2)
O1B 0.034(3) 0.048(4) 0.039(3) 0.002(3) -0.003(3) 0.019(2)
O3A 0.0130(19) 0.014(5) 0.016(2) 0.002(3) -0.0054(16) -0.001(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
Cu1 N1 1.998(3) 6 ?
Cu1 N1 1.998(3) 2_756 ?
Cu1 N1 1.998(3) 5_756 ?
Cu1 N1 1.998(3) . ?
Cu1 O3B 2.396(13) 5_756 ?
Cu1 O3B 2.396(13) 2_756 ?
Cu1 O3B 2.396(13) 6 ?
Cu1 O3B 2.396(13) . ?
Cu1 O3A 2.471(13) 6 ?
Cu1 O3A 2.471(13) 2_756 ?
Cu1 O3A 2.471(13) 5_756 ?
Cu1 O3A 2.471(13) . ?
C1 N3 1.312(6) . ?
C1 N1 1.365(5) . ?
C1 H1 0.9300 . ?
C2 N2 1.318(5) . ?
C2 N1 1.320(5) . ?
C2 H2 0.9300 . ?
C3 N2 1.451(4) 2_755 ?
C3 N2 1.451(4) . ?
C3 H3A 0.9700 . ?
C3 H3B 0.9700 . ?
N2 N3 1.354(4) . ?
Cl1 O1A 1.398(6) 6 ?
Cl1 O1A 1.398(6) . ?
Cl1 O3B 1.431(14) . ?
Cl1 O3B 1.431(14) 6 ?
Cl1 O2 1.431(4) . ?
Cl1 O3A 1.453(15) . ?
Cl1 O3A 1.453(15) 6 ?
Cl1 O1B 1.487(8) 6 ?
Cl1 O1B 1.487(8) . ?
O3B O3B 0.33(6) 6 ?
O1A O1A 1.697(15) 6 ?
O3A O3A 0.96(4) 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
N1 Cu1 N1 180.0 6 2_756 ?
N1 Cu1 N1 92.06(19) 6 5_756 ?
N1 Cu1 N1 87.94(19) 2_756 5_756 ?
N1 Cu1 N1 87.94(19) 6 . ?
N1 Cu1 N1 92.06(19) 2_756 . ?
N1 Cu1 N1 180.000(1) 5_756 . ?
N1 Cu1 O3B 88.3(5) 6 5_756 ?
N1 Cu1 O3B 91.7(5) 2_756 5_756 ?
N1 Cu1 O3B 97.2(6) 5_756 5_756 ?
N1 Cu1 O3B 82.8(6) . 5_756 ?
N1 Cu1 O3B 82.8(6) 6 2_756 ?
N1 Cu1 O3B 97.2(6) 2_756 2_756 ?
N1 Cu1 O3B 91.7(5) 5_756 2_756 ?
N1 Cu1 O3B 88.3(5) . 2_756 ?
O3B Cu1 O3B 7.9(13) 5_756 2_756 ?
N1 Cu1 O3B 97.2(6) 6 6 ?
N1 Cu1 O3B 82.8(6) 2_756 6 ?
N1 Cu1 O3B 88.3(5) 5_756 6 ?
N1 Cu1 O3B 91.7(5) . 6 ?
O3B Cu1 O3B 172.1(13) 5_756 6 ?
O3B Cu1 O3B 180.000(1) 2_756 6 ?
N1 Cu1 O3B 91.7(5) 6 . ?
N1 Cu1 O3B 88.3(5) 2_756 . ?
N1 Cu1 O3B 82.8(6) 5_756 . ?
N1 Cu1 O3B 97.2(6) . . ?
O3B Cu1 O3B 180.000(1) 5_756 . ?
O3B Cu1 O3B 172.1(13) 2_756 . ?
O3B Cu1 O3B 7.9(13) 6 . ?
N1 Cu1 O3A 85.9(4) 6 6 ?
N1 Cu1 O3A 94.1(4) 2_756 6 ?
N1 Cu1 O3A 78.6(4) 5_756 6 ?
N1 Cu1 O3A 101.4(4) . 6 ?
O3B Cu1 O3A 172.7(11) 5_756 6 ?
O3B Cu1 O3A 164.8(4) 2_756 6 ?
O3B Cu1 O3A 15.2(4) 6 6 ?
O3B Cu1 O3A 7.3(11) . 6 ?
N1 Cu1 O3A 94.1(4) 6 2_756 ?
N1 Cu1 O3A 85.9(4) 2_756 2_756 ?
N1 Cu1 O3A 101.4(4) 5_756 2_756 ?
N1 Cu1 O3A 78.6(4) . 2_756 ?
O3B Cu1 O3A 7.3(11) 5_756 2_756 ?
O3B Cu1 O3A 15.2(4) 2_756 2_756 ?
O3B Cu1 O3A 164.8(4) 6 2_756 ?
O3B Cu1 O3A 172.7(11) . 2_756 ?
O3A Cu1 O3A 180.0(3) 6 2_756 ?
N1 Cu1 O3A 78.6(4) 6 5_756 ?
N1 Cu1 O3A 101.4(4) 2_756 5_756 ?
N1 Cu1 O3A 85.9(4) 5_756 5_756 ?
N1 Cu1 O3A 94.1(4) . 5_756 ?
O3B Cu1 O3A 15.2(4) 5_756 5_756 ?
O3B Cu1 O3A 7.3(11) 2_756 5_756 ?
O3B Cu1 O3A 172.7(11) 6 5_756 ?
O3B Cu1 O3A 164.8(4) . 5_756 ?
O3A Cu1 O3A 157.7(9) 6 5_756 ?
O3A Cu1 O3A 22.3(9) 2_756 5_756 ?
N1 Cu1 O3A 101.4(4) 6 . ?
N1 Cu1 O3A 78.6(4) 2_756 . ?
N1 Cu1 O3A 94.1(4) 5_756 . ?
N1 Cu1 O3A 85.9(4) . . ?
O3B Cu1 O3A 164.8(4) 5_756 . ?
O3B Cu1 O3A 172.7(11) 2_756 . ?
O3B Cu1 O3A 7.3(11) 6 . ?
O3B Cu1 O3A 15.2(4) . . ?
O3A Cu1 O3A 22.3(9) 6 . ?
O3A Cu1 O3A 157.7(9) 2_756 . ?
O3A Cu1 O3A 180.000(1) 5_756 . ?
N3 C1 N1 114.1(4) . . ?
N3 C1 H1 122.9 . . ?
N1 C1 H1 122.9 . . ?
N2 C2 N1 110.8(3) . . ?
N2 C2 H2 124.6 . . ?
N1 C2 H2 124.6 . . ?
N2 C3 N2 110.3(4) 2_755 . ?
N2 C3 H3A 109.6 2_755 . ?
N2 C3 H3A 109.6 . . ?
N2 C3 H3B 109.6 2_755 . ?
N2 C3 H3B 109.6 . . ?
H3A C3 H3B 108.1 . . ?
C2 N1 C1 102.4(3) . . ?
C2 N1 Cu1 127.9(2) . . ?
C1 N1 Cu1 128.8(3) . . ?
C2 N2 N3 109.9(3) . . ?
C2 N2 C3 130.2(3) . . ?
N3 N2 C3 119.8(3) . . ?
C1 N3 N2 102.8(3) . . ?
O1A Cl1 O1A 74.7(6) 6 . ?
O1A Cl1 O3B 115.0(10) 6 . ?
O1A Cl1 O3B 124.3(9) . . ?
O1A Cl1 O3B 124.3(9) 6 6 ?
O1A Cl1 O3B 115.0(10) . 6 ?
O3B Cl1 O3B 13(2) . 6 ?
O1A Cl1 O2 113.5(3) 6 . ?
O1A Cl1 O2 113.5(3) . . ?
O3B Cl1 O2 111.0(7) . . ?
O3B Cl1 O2 111.0(7) 6 . ?
O1A Cl1 O3A 132.8(7) 6 . ?
O1A Cl1 O3A 106.2(8) . . ?
O3B Cl1 O3A 25.9(6) . . ?
O3B Cl1 O3A 12.6(17) 6 . ?
O2 Cl1 O3A 109.0(6) . . ?
O1A Cl1 O3A 106.2(8) 6 6 ?
O1A Cl1 O3A 132.8(7) . 6 ?
O3B Cl1 O3A 12.6(17) . 6 ?
O3B Cl1 O3A 25.9(6) 6 6 ?
O2 Cl1 O3A 109.0(6) . 6 ?
O3A Cl1 O3A 38.4(14) . 6 ?
O1A Cl1 O1B 36.4(3) 6 6 ?
O1A Cl1 O1B 109.8(5) . 6 ?
O3B Cl1 O1B 87.0(11) . 6 ?
O3B Cl1 O1B 99.6(11) 6 6 ?
O2 Cl1 O1B 106.6(3) . 6 ?
O3A Cl1 O1B 111.7(8) . 6 ?
O3A Cl1 O1B 75.5(8) 6 6 ?
O1A Cl1 O1B 109.8(5) 6 . ?
O1A Cl1 O1B 36.4(3) . . ?
O3B Cl1 O1B 99.6(11) . . ?
O3B Cl1 O1B 87.0(11) 6 . ?
O2 Cl1 O1B 106.6(3) . . ?
O3A Cl1 O1B 75.5(8) . . ?
O3A Cl1 O1B 111.7(8) 6 . ?
O1B Cl1 O1B 141.0(6) 6 . ?
O3B O3B Cl1 83.3(11) 6 . ?
O3B O3B Cu1 86.0(7) 6 . ?
Cl1 O3B Cu1 152.0(12) . . ?
Cl1 O1A O1A 52.6(3) . 6 ?
O3A O3A Cl1 70.8(7) 6 . ?
O3A O3A Cu1 78.8(5) 6 . ?
Cl1 O3A Cu1 141.6(11) . . ?

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
N2 C2 N1 C1 -1.2(5) . . . . ?
N2 C2 N1 Cu1 -171.1(3) . . . . ?
N3 C1 N1 C2 0.5(7) . . . . ?
N3 C1 N1 Cu1 170.3(4) . . . . ?
N1 Cu1 N1 C2 98.4(3) 6 . . . ?
N1 Cu1 N1 C2 -81.6(3) 2_756 . . . ?
N1 Cu1 N1 C2 -100(100) 5_756 . . . ?
O3B Cu1 N1 C2 -173.1(6) 5_756 . . . ?
O3B Cu1 N1 C2 -178.8(7) 2_756 . . . ?
O3B Cu1 N1 C2 1.2(7) 6 . . . ?
O3B Cu1 N1 C2 6.9(6) . . . . ?
O3A Cu1 N1 C2 12.9(5) 6 . . . ?
O3A Cu1 N1 C2 -167.1(5) 2_756 . . . ?
O3A Cu1 N1 C2 176.8(5) 5_756 . . . ?
O3A Cu1 N1 C2 -3.2(5) . . . . ?
N1 Cu1 N1 C1 -69.0(4) 6 . . . ?
N1 Cu1 N1 C1 111.0(4) 2_756 . . . ?
N1 Cu1 N1 C1 92(100) 5_756 . . . ?
O3B Cu1 N1 C1 19.6(7) 5_756 . . . ?
O3B Cu1 N1 C1 13.9(7) 2_756 . . . ?
O3B Cu1 N1 C1 -166.1(7) 6 . . . ?
O3B Cu1 N1 C1 -160.4(7) . . . . ?
O3A Cu1 N1 C1 -154.4(6) 6 . . . ?
O3A Cu1 N1 C1 25.6(6) 2_756 . . . ?
O3A Cu1 N1 C1 9.5(6) 5_756 . . . ?
O3A Cu1 N1 C1 -170.5(6) . . . . ?
N1 C2 N2 N3 1.6(5) . . . . ?
N1 C2 N2 C3 177.0(4) . . . . ?
N2 C3 N2 C2 -75.6(4) 2_755 . . . ?
N2 C3 N2 N3 99.4(4) 2_755 . . . ?
N1 C1 N3 N2 0.4(7) . . . . ?
C2 N2 N3 C1 -1.2(6) . . . . ?
C3 N2 N3 C1 -177.2(4) . . . . ?
O1A Cl1 O3B O3B -136.8(6) 6 . . 6 ?
O1A Cl1 O3B O3B -48.7(7) . . . 6 ?
O2 Cl1 O3B O3B 92.6(4) . . . 6 ?
O3A Cl1 O3B O3B 2(3) . . . 6 ?
O3A Cl1 O3B O3B 176(6) 6 . . 6 ?
O1B Cl1 O3B O3B -160.8(3) 6 . . 6 ?
O1B Cl1 O3B O3B -19.5(3) . . . 6 ?
O1A Cl1 O3B Cu1 155(3) 6 . . . ?
O1A Cl1 O3B Cu1 -117(3) . . . . ?
O3B Cl1 O3B Cu1 -68(3) 6 . . . ?
O2 Cl1 O3B Cu1 24(4) . . . . ?
O3A Cl1 O3B Cu1 -66(4) . . . . ?
O3A Cl1 O3B Cu1 107(7) 6 . . . ?
O1B Cl1 O3B Cu1 131(3) 6 . . . ?
O1B Cl1 O3B Cu1 -88(3) . . . . ?
N1 Cu1 O3B O3B -134.29(10) 6 . . 6 ?
N1 Cu1 O3B O3B 45.71(10) 2_756 . . 6 ?
N1 Cu1 O3B O3B 133.85(11) 5_756 . . 6 ?
N1 Cu1 O3B O3B -46.15(11) . . . 6 ?
O3B Cu1 O3B O3B -49(100) 5_756 . . 6 ?
O3B Cu1 O3B O3B 180.000(5) 2_756 . . 6 ?
O3A Cu1 O3B O3B -172(6) 6 . . 6 ?
O3A Cu1 O3B O3B 8(6) 2_756 . . 6 ?
O3A Cu1 O3B O3B 176(3) 5_756 . . 6 ?
O3A Cu1 O3B O3B -4(3) . . . 6 ?
N1 Cu1 O3B Cl1 -67(3) 6 . . . ?
N1 Cu1 O3B Cl1 113(3) 2_756 . . . ?
N1 Cu1 O3B Cl1 -158(3) 5_756 . . . ?
N1 Cu1 O3B Cl1 22(3) . . . . ?
O3B Cu1 O3B Cl1 19(100) 5_756 . . . ?
O3B Cu1 O3B Cl1 -112(3) 2_756 . . . ?
O3B Cu1 O3B Cl1 68(3) 6 . . . ?
O3A Cu1 O3B Cl1 -104(6) 6 . . . ?
O3A Cu1 O3B Cl1 76(6) 2_756 . . . ?
O3A Cu1 O3B Cl1 -116(4) 5_756 . . . ?
O3A Cu1 O3B Cl1 64(4) . . . . ?
O3B Cl1 O1A O1A -110.1(12) . . . 6 ?
O3B Cl1 O1A O1A -121.1(10) 6 . . 6 ?
O2 Cl1 O1A O1A 109.4(3) . . . 6 ?
O3A Cl1 O1A O1A -130.8(7) . . . 6 ?
O3A Cl1 O1A O1A -98.2(10) 6 . . 6 ?
O1B Cl1 O1A O1A -9.8(4) 6 . . 6 ?
O1B Cl1 O1A O1A -164.3(6) . . . 6 ?
O1A Cl1 O3A O3A 56.4(7) 6 . . 6 ?
O1A Cl1 O3A O3A 140.4(5) . . . 6 ?
O3B Cl1 O3A O3A 2(3) . . . 6 ?
O3B Cl1 O3A O3A 5(6) 6 . . 6 ?
O2 Cl1 O3A O3A -96.9(4) . . . 6 ?
O1B Cl1 O3A O3A 20.7(4) 6 . . 6 ?
O1B Cl1 O3A O3A 160.2(3) . . . 6 ?
O1A Cl1 O3A Cu1 96.1(15) 6 . . . ?
O1A Cl1 O3A Cu1 -179.9(13) . . . . ?
O3B Cl1 O3A Cu1 42(2) . . . . ?
O3B Cl1 O3A Cu1 44(5) 6 . . . ?
O2 Cl1 O3A Cu1 -57.2(16) . . . . ?
O3A Cl1 O3A Cu1 39.7(16) 6 . . . ?
O1B Cl1 O3A Cu1 60.3(16) 6 . . . ?
O1B Cl1 O3A Cu1 -160.1(16) . . . . ?
N1 Cu1 O3A O3A 46.99(12) 6 . . 6 ?
N1 Cu1 O3A O3A -133.01(12) 2_756 . . 6 ?
N1 Cu1 O3A O3A -45.94(11) 5_756 . . 6 ?
N1 Cu1 O3A O3A 134.06(11) . . . 6 ?
O3B Cu1 O3A O3A 176(3) 5_756 . . 6 ?
O3B Cu1 O3A O3A 172(6) 2_756 . . 6 ?
O3B Cu1 O3A O3A -8(6) 6 . . 6 ?
O3B Cu1 O3A O3A -4(3) . . . 6 ?
O3A Cu1 O3A O3A 180.0 2_756 . . 6 ?
O3A Cu1 O3A O3A -91(100) 5_756 . . 6 ?
N1 Cu1 O3A Cl1 9.1(16) 6 . . . ?
N1 Cu1 O3A Cl1 -170.9(16) 2_756 . . . ?
N1 Cu1 O3A Cl1 -83.9(15) 5_756 . . . ?
N1 Cu1 O3A Cl1 96.1(15) . . . . ?
O3B Cu1 O3A Cl1 138(2) 5_756 . . . ?
O3B Cu1 O3A Cl1 134(5) 2_756 . . . ?
O3B Cu1 O3A Cl1 -46(5) 6 . . . ?
O3B Cu1 O3A Cl1 -42(2) . . . . ?
O3A Cu1 O3A Cl1 -37.9(16) 6 . . . ?
O3A Cu1 O3A Cl1 142.1(16) 2_756 . . . ?
O3A Cu1 O3A Cl1 -129(100) 5_756 . . . ?

_diffrn_measured_fraction_theta_max 1.000
_diffrn_reflns_theta_full        25.01
_diffrn_measured_fraction_theta_full 1.000
_refine_diff_density_max         0.671
_refine_diff_density_min         -0.496
_refine_diff_density_rms         0.095

#===END

data_2
_database_code_depnum_ccdc_archive 'CCDC 842058'
#TrackingRef '- compound 1 to 4.cif'

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C12 H22 Cl2 Cu N12 O11'
_chemical_formula_weight         644.81

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'
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'
Cl Cl 0.1484 0.1585 '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'

_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_H-M   'P n n a'

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

_cell_length_a                   14.1980(6)
_cell_length_b                   21.2033(6)
_cell_length_c                   8.7574(3)
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_volume                     2636.37(16)
_cell_formula_units_Z            4
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    2433
_cell_measurement_theta_min      2.3928
_cell_measurement_theta_max      29.0760

_exptl_crystal_description       block
_exptl_crystal_colour            blue
_exptl_crystal_size_max          0.20
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.20
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.609
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1292
_exptl_absorpt_coefficient_mu    1.104
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.8094
_exptl_absorpt_correction_T_max  0.8094
_exptl_absorpt_process_details   
;
CrysAlisPro, Oxford Diffraction Ltd.,
Version 1.171.34.44 (release 25-10-2010 CrysAlis171 .NET)
(compiled Oct 25 2010,18:11:34)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;

_exptl_special_details           
;
?
;

_diffrn_ambient_temperature      293(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'SuperNova (Mo) X-ray Source'
_diffrn_radiation_monochromator  mirror
_diffrn_measurement_device_type  'SuperNova, Single source at offset), Eos'
_diffrn_measurement_method       '\w scans'
_diffrn_detector_area_resol_mean 16.2116
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            6375
_diffrn_reflns_av_R_equivalents  0.0294
_diffrn_reflns_av_sigmaI/netI    0.0407
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_k_min       -24
_diffrn_reflns_limit_k_max       25
_diffrn_reflns_limit_l_min       -10
_diffrn_reflns_limit_l_max       8
_diffrn_reflns_theta_min         2.73
_diffrn_reflns_theta_max         25.01
_reflns_number_total             2330
_reflns_number_gt                1746
_reflns_threshold_expression     >2sigma(I)

_computing_cell_refinement       
;
CrysAlisPro, Oxford Diffraction Ltd.,
Version 1.171.34.44 (release 25-10-2010 CrysAlis171 .NET)
(compiled Oct 25 2010,18:11:34)
;
_computing_data_collection       
;
CrysAlisPro, Oxford Diffraction Ltd.,
Version 1.171.34.44 (release 25-10-2010 CrysAlis171 .NET)
(compiled Oct 25 2010,18:11:34)
;
_computing_data_reduction        
;
CrysAlisPro, Oxford Diffraction Ltd.,
Version 1.171.34.44 (release 25-10-2010 CrysAlis171 .NET)
(compiled Oct 25 2010,18:11:34)
;
_computing_molecular_graphics    
;
O. V. Dolomanov, L. J. Bourhis, R. J. Gildea, J. A. K. Howard and H. Puschmann,
OLEX2: a complete structure solution, refinement and analysis program.
J. Appl. Cryst. (2009). 42, 339-341.
;
_computing_publication_material  
;
O. V. Dolomanov, L. J. Bourhis, R. J. Gildea, J. A. K. Howard and H. Puschmann,
OLEX2: a complete structure solution, refinement and analysis program.
J. Appl. Cryst. (2009). 42, 339-341.
;
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'

_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. It should be noted oxygen
atoms of two ClO~4~^ C^ and water molecules O10 and O11 in the compound
were treated by disorder and these atoms were refined anisotropically with
application of restrains on interatomic distances and thermal parameters
(DFIX, ISOR and SADI instructions in SHELXL).
;

_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^)+(0.1177P)^2^+4.0795P] 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         2330
_refine_ls_number_parameters     270
_refine_ls_number_restraints     171
_refine_ls_R_factor_all          0.0860
_refine_ls_R_factor_gt           0.0661
_refine_ls_wR_factor_ref         0.2057
_refine_ls_wR_factor_gt          0.1854
_refine_ls_goodness_of_fit_ref   1.072
_refine_ls_restrained_S_all      1.090
_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 0.05777(7) 0.2500 0.2500 0.0356(4) Uani 1 2 d S . .
N1 N 0.0565(3) 0.17219(18) 0.3787(5) 0.0379(10) Uani 1 1 d . . .
N2 N 0.0837(4) 0.0772(2) 0.4779(6) 0.0513(12) Uani 1 1 d . . .
N3 N 0.0110(3) 0.10597(18) 0.5521(4) 0.0382(10) Uani 1 1 d . . .
N4 N 0.0502(3) 0.12212(19) 0.8926(5) 0.0435(12) Uani 1 1 d . . .
N5 N 0.1176(4) 0.1610(2) 0.8337(5) 0.0517(13) Uani 1 1 d . . .
N6 N 0.0673(3) 0.19648(19) 1.0604(5) 0.0398(10) Uani 1 1 d . . .
C1 C -0.0039(4) 0.1620(2) 0.4910(6) 0.0418(13) Uani 1 1 d . . .
H1 H -0.0501 0.1903 0.5224 0.050 Uiso 1 1 calc R . .
C2 C 0.1088(4) 0.1189(2) 0.3760(6) 0.0460(13) Uani 1 1 d . . .
H2 H 0.1581 0.1125 0.3079 0.055 Uiso 1 1 calc R . .
C3 C -0.0391(4) 0.0755(2) 0.6777(6) 0.0489(15) Uani 1 1 d . . .
H3A H -0.0645 0.0356 0.6427 0.059 Uiso 1 1 calc R . .
H3B H -0.0916 0.1019 0.7085 0.059 Uiso 1 1 calc R . .
C4 C 0.0233(5) 0.0640(2) 0.8129(7) 0.0559(17) Uani 1 1 d . . .
H4A H -0.0091 0.0365 0.8840 0.067 Uiso 1 1 calc R . .
H4B H 0.0799 0.0425 0.7791 0.067 Uiso 1 1 calc R . .
C5 C 0.0223(4) 0.1441(2) 1.0261(6) 0.0438(13) Uani 1 1 d . . .
H5 H -0.0229 0.1252 1.0876 0.053 Uiso 1 1 calc R . .
C6 C 0.1251(4) 0.2050(3) 0.9373(6) 0.0489(14) Uani 1 1 d . . .
H6 H 0.1661 0.2390 0.9283 0.059 Uiso 1 1 calc R . .
Cl1 Cl 0.3170(5) 0.2607(4) 0.2459(14) 0.059(3) Uani 0.360(11) 1 d PDU . 1
O1 O 0.3481(12) 0.2957(8) 0.3787(15) 0.125(8) Uani 0.360(11) 1 d PDU . 1
O2 O 0.3940(9) 0.2228(6) 0.1930(18) 0.080(5) Uani 0.360(11) 1 d PDU . 1
O3 O 0.2900(10) 0.3046(7) 0.1290(18) 0.084(5) Uani 0.360(11) 1 d PDU . 1
O4 O 0.2388(8) 0.2222(6) 0.2864(18) 0.077(5) Uani 0.360(11) 1 d PDU . 1
Cl1' Cl 0.3132(10) 0.2590(8) 0.3034(18) 0.043(5) Uani 0.140(11) 1 d PDU . 2
O1' O 0.3046(17) 0.3223(9) 0.364(3) 0.072(11) Uani 0.140(11) 1 d PDU . 2
O2' O 0.4082(11) 0.2500 0.2500 0.037(7) Uani 0.28(2) 2 d SPDU . 2
O3' O 0.2478(15) 0.2515(18) 0.180(3) 0.10(2) Uani 0.140(11) 1 d PDU . 2
O4' O 0.2929(16) 0.2141(11) 0.422(3) 0.043(9) Uani 0.140(11) 1 d PDU . 2
Cl2 Cl 0.7500 0.5000 0.5958(3) 0.0681(7) Uani 1 2 d SDU . .
O5 O 0.7327(9) 0.5080(7) 0.7574(8) 0.091(5) Uani 0.50 1 d PDU . .
O6 O 0.7562(12) 0.4328(3) 0.5711(14) 0.127(5) Uani 0.50 1 d PDU . .
O7 O 0.8332(7) 0.5286(6) 0.5568(13) 0.109(4) Uani 0.50 1 d PDU . .
O8 O 0.6717(8) 0.5232(8) 0.5161(15) 0.176(7) Uani 0.50 1 d PDU . .
O9 O -0.1103(5) 0.2500 0.2500 0.075(2) Uani 1 2 d SU . .
O10 O 0.1659(7) 0.8836(6) 0.7673(11) 0.085(3) Uani 0.50 1 d PU . .
O11 O 0.2500 1.0000 0.604(3) 0.122(8) Uani 0.50 2 d SPU . .
O11' O 0.2139(18) 0.9686(12) 0.588(3) 0.094(7) Uani 0.25 1 d PU . .

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 0.0543(7) 0.0283(5) 0.0243(5) 0.0006(3) 0.000 0.000
N1 0.053(3) 0.032(2) 0.029(2) -0.0021(17) 0.001(2) 0.0056(19)
N2 0.074(3) 0.032(2) 0.048(3) -0.002(2) 0.003(3) 0.008(2)
N3 0.060(3) 0.0284(19) 0.026(2) 0.0009(16) -0.002(2) -0.003(2)
N4 0.070(3) 0.031(2) 0.029(2) 0.0006(18) -0.006(2) -0.002(2)
N5 0.068(3) 0.052(3) 0.035(2) -0.007(2) 0.011(2) -0.006(2)
N6 0.055(3) 0.036(2) 0.028(2) -0.0007(18) 0.001(2) 0.002(2)
C1 0.059(4) 0.034(2) 0.032(3) -0.001(2) 0.002(3) 0.001(2)
C2 0.062(4) 0.034(3) 0.042(3) 0.000(2) 0.002(3) 0.006(3)
C3 0.076(4) 0.035(3) 0.036(3) 0.002(2) -0.006(3) -0.019(3)
C4 0.106(5) 0.028(3) 0.034(3) -0.003(2) -0.002(3) -0.011(3)
C5 0.069(4) 0.035(3) 0.027(3) 0.001(2) 0.005(3) -0.010(3)
C6 0.061(4) 0.045(3) 0.041(3) -0.004(2) 0.002(3) -0.010(3)
Cl1 0.045(4) 0.066(7) 0.067(6) -0.012(4) 0.013(5) -0.010(3)
O1 0.123(11) 0.125(11) 0.126(11) -0.023(9) 0.003(9) -0.008(9)
O2 0.078(8) 0.077(8) 0.087(9) 0.007(7) 0.017(7) 0.019(7)
O3 0.079(8) 0.080(8) 0.092(9) 0.011(8) -0.008(7) 0.013(7)
O4 0.059(8) 0.085(8) 0.087(8) -0.007(7) 0.017(6) -0.029(6)
Cl1' 0.026(7) 0.061(8) 0.042(8) -0.010(6) 0.002(6) -0.001(7)
O1' 0.069(14) 0.068(13) 0.081(14) 0.002(9) 0.002(9) 0.002(9)
O2' 0.034(9) 0.043(10) 0.035(9) -0.001(7) 0.000 0.000
O3' 0.10(2) 0.10(2) 0.10(2) -0.009(10) -0.007(10) 0.008(10)
O4' 0.046(12) 0.045(12) 0.037(11) 0.006(9) 0.011(8) 0.000(9)
Cl2 0.0591(14) 0.0703(14) 0.0750(16) 0.000 0.000 -0.0067(12)
O5 0.098(9) 0.107(8) 0.069(5) -0.004(6) 0.020(6) 0.011(7)
O6 0.159(9) 0.095(7) 0.128(8) -0.019(6) 0.014(8) -0.023(7)
O7 0.088(7) 0.117(7) 0.123(8) -0.012(6) 0.033(6) -0.051(6)
O8 0.157(10) 0.189(11) 0.180(11) 0.002(9) -0.037(9) 0.007(9)
O9 0.064(4) 0.085(5) 0.075(5) 0.011(3) 0.000 0.000
O10 0.058(6) 0.107(8) 0.089(7) 0.012(5) -0.033(5) -0.051(6)
O11 0.124(12) 0.127(12) 0.115(11) 0.000 0.000 0.005(9)
O11' 0.091(11) 0.094(11) 0.095(11) 0.000(9) 0.006(9) 0.002(9)

_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 1.998(4) 3 ?
Cu1 N1 1.998(4) . ?
Cu1 N6 2.015(4) 3_556 ?
Cu1 N6 2.015(4) 1_554 ?
Cu1 O9 2.386(8) . ?
N1 C1 1.322(7) . ?
N1 C2 1.353(6) . ?
N2 C2 1.306(7) . ?
N2 N3 1.364(6) . ?
N3 C1 1.320(6) . ?
N3 C3 1.461(7) . ?
N4 C5 1.320(7) . ?
N4 N5 1.365(6) . ?
N4 C4 1.466(7) . ?
N5 C6 1.306(7) . ?
N6 C5 1.315(7) . ?
N6 C6 1.367(7) . ?
N6 Cu1 2.015(4) 1_556 ?
C3 C4 1.499(9) . ?
Cl1 Cl1 0.458(18) 3 ?
Cl1 O4 1.203(11) 3 ?
Cl1 O2 1.266(13) 3 ?
Cl1 O4 1.423(9) . ?
Cl1 O2 1.433(9) . ?
Cl1 O3 1.436(10) . ?
Cl1 O1 1.449(10) . ?
Cl1 O1 1.68(2) 3 ?
Cl1 O3 1.806(16) 3 ?
O1 O2 0.99(3) 3 ?
O1 Cl1 1.68(2) 3 ?
O2 O1 0.99(3) 3 ?
O2 Cl1 1.266(13) 3 ?
O2 O2 1.52(3) 3 ?
O3 O4 1.18(2) 3 ?
O3 Cl1 1.806(16) 3 ?
O4 O3 1.18(2) 3 ?
O4 Cl1 1.203(11) 3 ?
O4 O4 1.34(2) 3 ?
Cl1' O3' 0.966(18) 3 ?
Cl1' Cl1' 1.01(3) 3 ?
Cl1' O3' 1.435(10) . ?
Cl1' O4' 1.437(10) . ?
Cl1' O2' 1.440(10) . ?
Cl1' O1' 1.450(10) . ?
Cl1' O4' 2.07(3) 3 ?
O1' O3' 1.80(5) 3 ?
O2' Cl1' 1.440(10) 3 ?
O3' Cl1' 0.966(18) 3 ?
O3' O3' 1.23(5) 3 ?
O3' O4' 1.32(6) 3 ?
O3' O1' 1.80(5) 3 ?
O4' O3' 1.32(6) 3 ?
O4' Cl1' 2.07(3) 3 ?
Cl2 O7 1.371(7) . ?
Cl2 O7 1.371(7) 2_665 ?
Cl2 O8 1.403(8) 2_665 ?
Cl2 O8 1.403(8) . ?
Cl2 O6 1.443(7) 2_665 ?
Cl2 O6 1.443(7) . ?
Cl2 O5 1.446(6) 2_665 ?
Cl2 O5 1.446(6) . ?
O5 O5 0.60(3) 2_665 ?
O6 O8 1.466(16) 2_665 ?
O6 O7 1.515(15) 2_665 ?
O7 O8 1.158(15) 2_665 ?
O7 O6 1.515(15) 2_665 ?
O8 O7 1.158(15) 2_665 ?
O8 O6 1.466(16) 2_665 ?
O11 O11' 0.85(3) 2_575 ?
O11 O11' 0.85(3) . ?
O11' O11' 1.68(5) 2_575 ?

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 178.9(3) 3 . ?
N1 Cu1 N6 90.02(15) 3 3_556 ?
N1 Cu1 N6 90.05(15) . 3_556 ?
N1 Cu1 N6 90.05(15) 3 1_554 ?
N1 Cu1 N6 90.02(15) . 1_554 ?
N6 Cu1 N6 172.3(3) 3_556 1_554 ?
N1 Cu1 O9 89.47(13) 3 . ?
N1 Cu1 O9 89.47(13) . . ?
N6 Cu1 O9 93.84(13) 3_556 . ?
N6 Cu1 O9 93.84(13) 1_554 . ?
C1 N1 C2 103.5(4) . . ?
C1 N1 Cu1 124.1(3) . . ?
C2 N1 Cu1 132.4(4) . . ?
C2 N2 N3 103.3(4) . . ?
C1 N3 N2 109.3(4) . . ?
C1 N3 C3 128.7(5) . . ?
N2 N3 C3 122.0(4) . . ?
C5 N4 N5 109.4(4) . . ?
C5 N4 C4 129.8(5) . . ?
N5 N4 C4 120.7(4) . . ?
C6 N5 N4 103.0(4) . . ?
C5 N6 C6 102.8(4) . . ?
C5 N6 Cu1 129.1(4) . 1_556 ?
C6 N6 Cu1 128.0(4) . 1_556 ?
N3 C1 N1 110.2(5) . . ?
N2 C2 N1 113.8(5) . . ?
N3 C3 C4 112.3(5) . . ?
N4 C4 C3 113.2(4) . . ?
N6 C5 N4 110.8(5) . . ?
N5 C6 N6 113.9(5) . . ?
Cl1 Cl1 O4 109.6(11) 3 3 ?
Cl1 Cl1 O2 102.0(18) 3 3 ?
O4 Cl1 O2 144.4(16) 3 3 ?
Cl1 Cl1 O4 52.8(9) 3 . ?
O4 Cl1 O4 60.7(12) 3 . ?
O2 Cl1 O4 136.6(12) 3 . ?
Cl1 Cl1 O2 59.8(16) 3 . ?
O4 Cl1 O2 142.9(16) 3 . ?
O2 Cl1 O2 68.5(14) 3 . ?
O4 Cl1 O2 110.8(7) . . ?
Cl1 Cl1 O3 139(3) 3 . ?
O4 Cl1 O3 52.4(11) 3 . ?
O2 Cl1 O3 110.7(11) 3 . ?
O4 Cl1 O3 109.9(6) . . ?
O2 Cl1 O3 109.6(7) . . ?
Cl1 Cl1 O1 112(3) 3 . ?
O4 Cl1 O1 108.4(15) 3 . ?
O2 Cl1 O1 42.0(13) 3 . ?
O4 Cl1 O1 109.4(7) . . ?
O2 Cl1 O1 108.3(7) . . ?
O3 Cl1 O1 108.7(7) . . ?
Cl1 Cl1 O1 53(3) 3 3 ?
O4 Cl1 O1 107.8(13) 3 3 ?
O2 Cl1 O1 104.2(8) 3 3 ?
O4 Cl1 O1 87.6(10) . 3 ?
O2 Cl1 O1 35.9(11) . 3 ?
O3 Cl1 O1 93.9(9) . 3 ?
O1 Cl1 O1 143.9(12) . 3 ?
Cl1 Cl1 O3 32(3) 3 3 ?
O4 Cl1 O3 100.3(8) 3 3 ?
O2 Cl1 O3 98.0(10) 3 3 ?
O4 Cl1 O3 40.9(8) . 3 ?
O2 Cl1 O3 85.9(8) . 3 ?
O3 Cl1 O3 150.7(10) . 3 ?
O1 Cl1 O3 88.4(9) . 3 ?
O1 Cl1 O3 84.5(8) 3 3 ?
O2 O1 Cl1 59.1(8) 3 . ?
O2 O1 Cl1 58.4(10) 3 3 ?
Cl1 O1 Cl1 14.6(7) . 3 ?
O1 O2 Cl1 79.0(11) 3 3 ?
O1 O2 Cl1 85.7(13) 3 . ?
Cl1 O2 Cl1 18.2(8) 3 . ?
O1 O2 O2 135.9(11) 3 3 ?
Cl1 O2 O2 61.0(10) 3 3 ?
Cl1 O2 O2 50.6(7) . 3 ?
O4 O3 Cl1 53.6(6) 3 . ?
O4 O3 Cl1 51.9(7) 3 3 ?
Cl1 O3 Cl1 9.6(8) . 3 ?
O3 O4 Cl1 74.0(9) 3 3 ?
O3 O4 O4 136.0(13) 3 3 ?
Cl1 O4 O4 67.8(8) 3 3 ?
O3 O4 Cl1 87.2(10) 3 . ?
Cl1 O4 Cl1 17.7(8) 3 . ?
O4 O4 Cl1 51.5(6) 3 . ?
O3' Cl1' Cl1' 93(2) 3 3 ?
O3' Cl1' O3' 58(3) 3 . ?
Cl1' Cl1' O3' 42.2(10) 3 . ?
O3' Cl1' O4' 63(3) 3 . ?
Cl1' Cl1' O4' 115(2) 3 . ?
O3' Cl1' O4' 110.0(7) . . ?
O3' Cl1' O2' 157(3) 3 . ?
Cl1' Cl1' O2' 69.5(7) 3 . ?
O3' Cl1' O2' 110.3(8) . . ?
O4' Cl1' O2' 109.6(7) . . ?
O3' Cl1' O1' 94(3) 3 . ?
Cl1' Cl1' O1' 134(2) 3 . ?
O3' Cl1' O1' 109.0(7) . . ?
O4' Cl1' O1' 109.2(7) . . ?
O2' Cl1' O1' 108.7(7) . . ?
O3' Cl1' O4' 94(2) 3 3 ?
Cl1' Cl1' O4' 39.0(15) 3 3 ?
O3' Cl1' O4' 39.0(15) . 3 ?
O4' Cl1' O4' 147.3(15) . 3 ?
O2' Cl1' O4' 81.8(12) . 3 ?
O1' Cl1' O4' 94.8(12) . 3 ?
Cl1' O1' O3' 32.3(8) . 3 ?
Cl1' O2' Cl1' 41.0(14) . 3 ?
Cl1' O3' O3' 81(3) 3 3 ?
Cl1' O3' O4' 76(3) 3 3 ?
O3' O3' O4' 135(3) 3 3 ?
Cl1' O3' Cl1' 44.6(19) 3 . ?
O3' O3' Cl1' 41.6(10) 3 . ?
O4' O3' Cl1' 97.7(12) 3 . ?
Cl1' O3' O1' 53(3) 3 3 ?
O3' O3' O1' 100(3) 3 3 ?
O4' O3' O1' 97(3) 3 3 ?
Cl1' O3' O1' 88.2(10) . 3 ?
O3' O4' Cl1' 40.8(11) 3 . ?
O3' O4' Cl1' 43.3(9) 3 3 ?
Cl1' O4' Cl1' 26.2(10) . 3 ?
O7 Cl2 O7 151.1(10) . 2_665 ?
O7 Cl2 O8 49.3(6) . 2_665 ?
O7 Cl2 O8 113.8(6) 2_665 2_665 ?
O7 Cl2 O8 113.8(6) . . ?
O7 Cl2 O8 49.3(6) 2_665 . ?
O8 Cl2 O8 120.3(12) 2_665 . ?
O7 Cl2 O6 65.1(6) . 2_665 ?
O7 Cl2 O6 110.3(5) 2_665 2_665 ?
O8 Cl2 O6 108.7(5) 2_665 2_665 ?
O8 Cl2 O6 62.0(6) . 2_665 ?
O7 Cl2 O6 110.3(5) . . ?
O7 Cl2 O6 65.1(6) 2_665 . ?
O8 Cl2 O6 62.0(6) 2_665 . ?
O8 Cl2 O6 108.7(5) . . ?
O6 Cl2 O6 162.8(10) 2_665 . ?
O7 Cl2 O5 98.6(9) . 2_665 ?
O7 Cl2 O5 109.8(5) 2_665 2_665 ?
O8 Cl2 O5 108.1(6) 2_665 2_665 ?
O8 Cl2 O5 131.6(10) . 2_665 ?
O6 Cl2 O5 105.8(5) 2_665 2_665 ?
O6 Cl2 O5 91.2(9) . 2_665 ?
O7 Cl2 O5 109.8(5) . . ?
O7 Cl2 O5 98.6(9) 2_665 . ?
O8 Cl2 O5 131.6(10) 2_665 . ?
O8 Cl2 O5 108.1(6) . . ?
O6 Cl2 O5 91.2(9) 2_665 . ?
O6 Cl2 O5 105.8(5) . . ?
O5 Cl2 O5 23.9(10) 2_665 . ?
O5 O5 Cl2 78.1(5) 2_665 . ?
Cl2 O6 O8 57.6(5) . 2_665 ?
Cl2 O6 O7 55.2(4) . 2_665 ?
O8 O6 O7 102.4(9) 2_665 2_665 ?
O8 O7 Cl2 66.8(6) 2_665 . ?
O8 O7 O6 119.2(11) 2_665 2_665 ?
Cl2 O7 O6 59.8(4) . 2_665 ?
O7 O8 Cl2 63.9(5) 2_665 . ?
O7 O8 O6 122.9(8) 2_665 2_665 ?
Cl2 O8 O6 60.4(5) . 2_665 ?
O11' O11 O11' 161(6) 2_575 . ?
O11 O11' O11' 9(3) . 2_575 ?

_diffrn_measured_fraction_theta_max 0.999
_diffrn_reflns_theta_full        25.01
_diffrn_measured_fraction_theta_full 0.999
_refine_diff_density_max         0.923
_refine_diff_density_min         -0.595
_refine_diff_density_rms         0.117

#===END

data_3
_database_code_depnum_ccdc_archive 'CCDC 842059'
#TrackingRef '- compound 1 to 4.cif'

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C14 H27 Cl2 Cu N12 O11.50'
_chemical_formula_weight         681.92

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'
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'
N N 0.0061 0.0033 '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'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_H-M   Pna21

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

_cell_length_a                   18.2592(6)
_cell_length_b                   12.6726(4)
_cell_length_c                   12.0365(5)
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_volume                     2785.14(17)
_cell_formula_units_Z            4
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    5589
_cell_measurement_theta_min      2.5812
_cell_measurement_theta_max      29.1635

_exptl_crystal_description       ?
_exptl_crystal_colour            blue
_exptl_crystal_size_max          0.1
_exptl_crystal_size_mid          0.1
_exptl_crystal_size_min          0.1
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.626
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1400
_exptl_absorpt_coefficient_mu    1.052
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.72896
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_process_details   ?

_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  ?
_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            7613
_diffrn_reflns_av_R_equivalents  0.0216
_diffrn_reflns_av_sigmaI/netI    0.0324
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_h_max       21
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_l_min       -9
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_theta_min         2.59
_diffrn_reflns_theta_max         25.01
_reflns_number_total             4052
_reflns_number_gt                3721
_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. It should be noted oxygen
atoms of one ClO~4~^ C^ in the compoud were treated by disorder and
these atoms were refined anisotropically with application of restrains on
interatomic distances and thermal parameters (DFIX, ISOR and SADI
instructions in SHELXL).
;

_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^)+(0.0617P)^2^+0.2309P] 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   0.429(17)
_refine_ls_number_reflns         4052
_refine_ls_number_parameters     408
_refine_ls_number_restraints     87
_refine_ls_R_factor_all          0.0386
_refine_ls_R_factor_gt           0.0348
_refine_ls_wR_factor_ref         0.0968
_refine_ls_wR_factor_gt          0.0954
_refine_ls_goodness_of_fit_ref   1.108
_refine_ls_restrained_S_all      1.172
_refine_ls_shift/su_max          0.019
_refine_ls_shift/su_mean         0.002

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
N12 N 0.19483(18) 0.7758(3) -0.0533(3) 0.0158(8) Uani 1 1 d . . .
C14 C 0.1392(2) 0.7497(3) 0.0127(4) 0.0201(10) Uani 1 1 d . . .
H14 H 0.1018 0.7032 -0.0062 0.024 Uiso 1 1 calc R . .
C13 C 0.2339(2) 0.8447(3) 0.0098(4) 0.0208(10) Uani 1 1 d . . .
H13 H 0.2767 0.8767 -0.0150 0.025 Uiso 1 1 calc R . .
N11 N 0.20607(19) 0.8623(3) 0.1087(3) 0.0228(9) Uani 1 1 d . . .
N10 N 0.14460(18) 0.7991(3) 0.1086(3) 0.0172(8) Uani 1 1 d . . .
C12 C 0.0911(2) 0.8040(4) 0.1982(4) 0.0265(11) Uani 1 1 d . . .
H12A H 0.0551 0.7487 0.1871 0.032 Uiso 1 1 calc R . .
H12B H 0.0657 0.8711 0.1941 0.032 Uiso 1 1 calc R . .
C11 C 0.1233(2) 0.7924(4) 0.3116(4) 0.0244(11) Uani 1 1 d . . .
H11A H 0.0861 0.8095 0.3663 0.029 Uiso 1 1 calc R . .
H11B H 0.1628 0.8429 0.3199 0.029 Uiso 1 1 calc R . .
N6 N 0.19130(18) 1.5862(3) 0.8208(3) 0.0185(9) Uani 1 1 d . . .
C6 C 0.2210(3) 1.5266(3) 0.9041(5) 0.0323(13) Uani 1 1 d . . .
H6 H 0.2559 1.5522 0.9534 0.039 Uiso 1 1 calc R . .
C7 C 0.1448(2) 1.5206(3) 0.7721(5) 0.0191(10) Uani 1 1 d . . .
H7 H 0.1154 1.5372 0.7115 0.023 Uiso 1 1 calc R . .
N5 N 0.1955(2) 1.4297(3) 0.9079(4) 0.0346(11) Uani 1 1 d . . .
N4 N 0.14653(18) 1.4282(2) 0.8226(3) 0.0187(9) Uani 1 1 d . . .
C5 C 0.1037(2) 1.3332(3) 0.7998(5) 0.0229(10) Uani 1 1 d . . .
H5A H 0.0728 1.3451 0.7355 0.027 Uiso 1 1 calc R . .
H5B H 0.0722 1.3181 0.8628 0.027 Uiso 1 1 calc R . .
C4 C 0.1534(2) 1.2393(3) 0.7783(6) 0.0238(10) Uani 1 1 d . . .
H4A H 0.1792 1.2211 0.8460 0.029 Uiso 1 1 calc R . .
H4B H 0.1894 1.2579 0.7223 0.029 Uiso 1 1 calc R . .
Cu1 Cu 0.20698(2) 0.73858(3) 0.78428(6) 0.01418(14) Uani 1 1 d . . .
C1 C 0.2372(2) 0.9508(3) 0.6699(4) 0.0208(10) Uani 1 1 d . . .
H1 H 0.2773 0.9245 0.6313 0.025 Uiso 1 1 calc R . .
C2 C 0.1467(2) 0.9590(3) 0.7790(5) 0.0175(8) Uani 1 1 d . . .
H2 H 0.1105 0.9433 0.8307 0.021 Uiso 1 1 calc R . .
C3 C 0.1090(2) 1.1449(3) 0.7387(4) 0.0222(11) Uani 1 1 d . . .
H3A H 0.0693 1.1316 0.7905 0.027 Uiso 1 1 calc R . .
H3B H 0.0876 1.1606 0.6668 0.027 Uiso 1 1 calc R . .
C8 C 0.1697(3) 0.7305(3) 0.5401(4) 0.0196(10) Uani 1 1 d . . .
H8 H 0.1343 0.7831 0.5454 0.024 Uiso 1 1 calc R . .
C9 C 0.2539(2) 0.6230(3) 0.5744(4) 0.0228(10) Uani 1 1 d . . .
H9 H 0.2897 0.5863 0.6136 0.027 Uiso 1 1 calc R . .
C10 C 0.1529(2) 0.6818(3) 0.3359(4) 0.0215(10) Uani 1 1 d . . .
H10A H 0.1132 0.6311 0.3311 0.026 Uiso 1 1 calc R . .
H10B H 0.1893 0.6633 0.2806 0.026 Uiso 1 1 calc R . .
Cl1 Cl 0.02461(7) 0.46812(12) 0.49941(14) 0.0451(4) Uani 1 1 d D . .
Cl2 Cl 0.01369(7) 0.07004(10) 0.05035(13) 0.0397(3) Uani 1 1 d . . .
N1 N 0.19769(18) 0.8916(3) 0.7442(3) 0.0164(8) Uani 1 1 d . . .
N2 N 0.21361(19) 1.0472(3) 0.6583(3) 0.0212(9) Uani 1 1 d . . .
N3 N 0.15502(18) 1.0505(2) 0.7299(3) 0.0169(8) Uani 1 1 d . . .
N7 N 0.21084(18) 0.6980(3) 0.6220(3) 0.0172(8) Uani 1 1 d . . .
N8 N 0.2407(2) 0.6069(3) 0.4684(3) 0.0232(9) Uani 1 1 d . . .
N9 N 0.18592(18) 0.6770(3) 0.4472(3) 0.0170(8) Uani 1 1 d . . .
O1 O 0.0535(2) 0.7481(3) 0.7761(7) 0.0531(12) Uani 1 1 d . . .
H1A H 0.0301 0.7921 0.7368 0.064 Uiso 1 1 d R . .
H1B H 0.0326 0.6882 0.7825 0.064 Uiso 1 1 d R . .
O2 O 0.32802(18) 0.7401(2) 0.8016(4) 0.0372(10) Uani 1 1 d . . .
H2A H 0.3446 0.7129 0.8608 0.045 Uiso 1 1 d R . .
H2B H 0.3601 0.7535 0.7526 0.045 Uiso 1 1 d R . .
O3 O -0.0190(4) 0.4429(5) 0.5945(7) 0.065(3) Uani 0.640(11) 1 d PDU A 1
O4 O 0.0224(5) 0.5872(4) 0.4941(8) 0.079(3) Uani 0.640(11) 1 d PDU A 1
O5 O -0.0039(5) 0.4291(8) 0.4029(7) 0.096(4) Uani 0.640(11) 1 d PDU A 1
O6 O 0.0992(3) 0.4462(6) 0.5189(6) 0.076(3) Uani 0.640(11) 1 d PDU A 1
O3' O -0.0517(5) 0.4729(12) 0.5369(12) 0.074(6) Uani 0.360(11) 1 d PDU A 2
O4' O 0.0624(7) 0.5537(9) 0.5361(10) 0.069(5) Uani 0.360(11) 1 d PDU A 2
O5' O 0.0199(7) 0.4650(10) 0.3782(7) 0.051(4) Uani 0.360(11) 1 d PDU A 2
O6' O 0.0530(9) 0.3694(9) 0.5354(12) 0.128(9) Uani 0.360(11) 1 d PDU A 2
O7 O 0.0251(3) 0.0725(4) 0.1687(4) 0.0755(15) Uani 1 1 d . . .
O8 O -0.0632(2) 0.0523(4) 0.0376(5) 0.0670(15) Uani 1 1 d . . .
O9 O 0.0536(3) -0.0123(4) 0.0055(5) 0.090(2) Uani 1 1 d . . .
O10 O 0.0333(3) 0.1681(3) 0.0012(5) 0.0724(15) Uani 1 1 d . . .
O11 O 0.4111(3) 0.8365(4) 0.6431(5) 0.0840(18) Uani 1 1 d . . .
H11C H 0.4331 0.8501 0.5822 0.101 Uiso 1 1 d R . .
H11D H 0.4381 0.8442 0.6999 0.101 Uiso 1 1 d R . .
O12 O 0.4214(4) 0.6749(6) 0.9622(7) 0.046(2) Uani 0.50 1 d P . .
H12C H 0.4592 0.7119 0.9498 0.055 Uiso 0.50 1 d PR . .
H12D H 0.4123 0.6298 0.9121 0.055 Uiso 0.50 1 d PR . .

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
N12 0.0215(19) 0.0138(18) 0.012(2) 0.0011(16) -0.0026(16) -0.0017(13)
C14 0.024(2) 0.024(2) 0.013(3) 0.001(2) 0.002(2) -0.0023(17)
C13 0.026(2) 0.019(2) 0.018(3) 0.001(2) -0.002(2) -0.0057(18)
N11 0.027(2) 0.027(2) 0.015(2) -0.0066(18) -0.0019(17) -0.0046(15)
N10 0.0196(18) 0.0191(18) 0.013(2) 0.0008(16) 0.0006(16) 0.0014(14)
C12 0.026(2) 0.040(3) 0.014(2) 0.001(2) 0.004(2) 0.014(2)
C11 0.032(2) 0.029(2) 0.012(3) -0.0049(19) 0.003(2) 0.0108(19)
N6 0.0264(18) 0.0152(16) 0.014(2) -0.0003(15) -0.0039(16) 0.0007(14)
C6 0.048(3) 0.018(2) 0.031(3) 0.002(2) -0.023(3) -0.006(2)
C7 0.0228(19) 0.0121(18) 0.022(3) -0.004(2) -0.005(2) 0.0027(14)
N5 0.056(3) 0.020(2) 0.027(3) 0.005(2) -0.017(2) -0.0035(17)
N4 0.0225(17) 0.0112(17) 0.022(2) -0.0022(15) -0.0015(16) 0.0011(13)
C5 0.025(2) 0.0100(17) 0.034(3) -0.003(2) 0.002(2) -0.0025(15)
C4 0.0167(17) 0.0146(17) 0.040(3) 0.002(3) -0.003(3) 0.0013(14)
Cu1 0.0225(2) 0.0094(2) 0.0107(3) 0.0006(3) 0.0013(3) -0.00060(17)
C1 0.024(2) 0.022(2) 0.016(3) 0.004(2) 0.005(2) 0.0015(18)
C2 0.0244(19) 0.0130(17) 0.015(2) -0.002(2) 0.000(2) -0.0018(14)
C3 0.019(2) 0.0130(19) 0.035(3) -0.0036(19) -0.006(2) 0.0042(16)
C8 0.025(2) 0.015(2) 0.019(3) 0.001(2) 0.005(2) 0.0023(17)
C9 0.033(2) 0.019(2) 0.016(2) 0.001(2) 0.000(2) 0.0102(19)
C10 0.023(2) 0.028(2) 0.013(2) -0.001(2) 0.002(2) -0.0055(19)
Cl1 0.0323(6) 0.0624(9) 0.0407(9) -0.0034(8) -0.0055(7) -0.0074(6)
Cl2 0.0444(7) 0.0382(7) 0.0365(8) 0.0083(7) 0.0056(7) 0.0152(6)
N1 0.0230(18) 0.0147(16) 0.012(2) -0.0024(15) 0.0023(15) -0.0005(14)
N2 0.0267(19) 0.0165(18) 0.020(2) 0.0017(17) 0.0102(18) 0.0023(15)
N3 0.0207(17) 0.0112(16) 0.019(2) -0.0002(15) 0.0048(16) -0.0004(14)
N7 0.0257(19) 0.0143(19) 0.012(2) 0.0030(17) 0.0022(16) 0.0015(15)
N8 0.032(2) 0.0200(19) 0.017(2) 0.0004(17) 0.0017(18) 0.0090(15)
N9 0.0213(17) 0.0139(18) 0.016(2) 0.0009(17) 0.0020(16) 0.0010(13)
O1 0.058(2) 0.0410(19) 0.060(3) 0.009(2) -0.022(3) -0.0103(16)
O2 0.0241(16) 0.056(2) 0.031(3) 0.0106(19) 0.0010(19) 0.0018(14)
O3 0.060(5) 0.061(4) 0.075(6) 0.036(4) 0.020(4) 0.003(3)
O4 0.081(6) 0.045(4) 0.111(7) -0.010(4) 0.021(5) -0.011(4)
O5 0.083(6) 0.104(7) 0.101(8) -0.027(6) -0.059(6) -0.022(5)
O6 0.032(3) 0.126(7) 0.069(6) -0.018(5) -0.013(4) 0.029(4)
O3' 0.064(8) 0.081(9) 0.078(9) -0.019(7) 0.015(7) -0.033(6)
O4' 0.066(8) 0.077(8) 0.063(8) 0.007(7) -0.022(7) -0.049(7)
O5' 0.057(7) 0.051(7) 0.045(7) 0.003(6) -0.025(6) -0.017(6)
O6' 0.144(12) 0.134(11) 0.107(12) 0.002(9) -0.005(9) 0.012(9)
O7 0.117(4) 0.074(3) 0.036(3) -0.001(3) -0.009(3) 0.024(3)
O8 0.048(2) 0.063(3) 0.090(4) 0.020(3) 0.010(3) 0.010(2)
O9 0.108(4) 0.104(4) 0.058(4) 0.015(3) 0.037(3) 0.079(3)
O10 0.096(3) 0.055(3) 0.066(4) 0.029(3) -0.006(3) -0.026(2)
O11 0.063(3) 0.108(4) 0.082(4) 0.045(3) 0.024(3) 0.005(3)
O12 0.063(5) 0.046(4) 0.029(5) 0.021(4) -0.010(4) 0.014(4)

_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
N12 C14 1.331(6) . ?
N12 C13 1.359(5) . ?
N12 Cu1 2.023(4) 1_554 ?
C14 N10 1.317(6) . ?
C14 H14 0.9300 . ?
C13 N11 1.314(6) . ?
C13 H13 0.9300 . ?
N11 N10 1.379(5) . ?
N10 C12 1.457(6) . ?
C12 C11 1.494(6) . ?
C12 H12A 0.9700 . ?
C12 H12B 0.9700 . ?
C11 C10 1.529(6) . ?
C11 H11A 0.9700 . ?
C11 H11B 0.9700 . ?
N6 C7 1.325(5) . ?
N6 C6 1.367(6) . ?
N6 Cu1 2.001(3) 1_565 ?
C6 N5 1.313(6) . ?
C6 H6 0.9300 . ?
C7 N4 1.319(5) . ?
C7 H7 0.9300 . ?
N5 N4 1.362(5) . ?
N4 C5 1.461(5) . ?
C5 C4 1.518(5) . ?
C5 H5A 0.9700 . ?
C5 H5B 0.9700 . ?
C4 C3 1.522(6) . ?
C4 H4A 0.9700 . ?
C4 H4B 0.9700 . ?
Cu1 N6 2.001(3) 1_545 ?
Cu1 N1 2.006(3) . ?
Cu1 N7 2.021(4) . ?
Cu1 N12 2.023(4) 1_556 ?
Cu1 O2 2.220(3) . ?
Cu1 O1 2.807(4) . ?
C1 N2 1.302(5) . ?
C1 N1 1.372(5) . ?
C1 H1 0.9300 . ?
C2 N3 1.311(5) . ?
C2 N1 1.330(5) . ?
C2 H2 0.9300 . ?
C3 N3 1.466(5) . ?
C3 H3A 0.9700 . ?
C3 H3B 0.9700 . ?
C8 N7 1.306(6) . ?
C8 N9 1.341(6) . ?
C8 H8 0.9300 . ?
C9 N8 1.315(6) . ?
C9 N7 1.360(5) . ?
C9 H9 0.9300 . ?
C10 N9 1.470(6) . ?
C10 H10A 0.9700 . ?
C10 H10B 0.9700 . ?
Cl1 O4' 1.360(8) . ?
Cl1 O5 1.366(6) . ?
Cl1 O6 1.410(5) . ?
Cl1 O6' 1.421(9) . ?
Cl1 O3 1.430(6) . ?
Cl1 O5' 1.462(8) . ?
Cl1 O3' 1.467(8) . ?
Cl1 O4 1.511(6) . ?
Cl2 O9 1.382(5) . ?
Cl2 O10 1.423(4) . ?
Cl2 O8 1.431(5) . ?
Cl2 O7 1.439(5) . ?
N2 N3 1.375(5) . ?
N8 N9 1.363(5) . ?
O1 H1A 0.8465 . ?
O1 H1B 0.8535 . ?
O2 H2A 0.8468 . ?
O2 H2B 0.8490 . ?
O11 H11C 0.8529 . ?
O11 H11D 0.8484 . ?
O12 H12C 0.8469 . ?
O12 H12D 0.8459 . ?

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
C14 N12 C13 103.1(4) . . ?
C14 N12 Cu1 127.0(3) . 1_554 ?
C13 N12 Cu1 129.2(3) . 1_554 ?
N10 C14 N12 110.3(4) . . ?
N10 C14 H14 124.8 . . ?
N12 C14 H14 124.8 . . ?
N11 C13 N12 114.3(4) . . ?
N11 C13 H13 122.8 . . ?
N12 C13 H13 122.8 . . ?
C13 N11 N10 102.4(4) . . ?
C14 N10 N11 109.8(4) . . ?
C14 N10 C12 128.2(4) . . ?
N11 N10 C12 121.4(4) . . ?
N10 C12 C11 114.0(4) . . ?
N10 C12 H12A 108.7 . . ?
C11 C12 H12A 108.7 . . ?
N10 C12 H12B 108.7 . . ?
C11 C12 H12B 108.7 . . ?
H12A C12 H12B 107.6 . . ?
C12 C11 C10 113.9(4) . . ?
C12 C11 H11A 108.8 . . ?
C10 C11 H11A 108.8 . . ?
C12 C11 H11B 108.8 . . ?
C10 C11 H11B 108.8 . . ?
H11A C11 H11B 107.7 . . ?
C7 N6 C6 103.4(4) . . ?
C7 N6 Cu1 126.9(3) . 1_565 ?
C6 N6 Cu1 129.6(3) . 1_565 ?
N5 C6 N6 113.7(4) . . ?
N5 C6 H6 123.1 . . ?
N6 C6 H6 123.1 . . ?
N4 C7 N6 109.7(4) . . ?
N4 C7 H7 125.1 . . ?
N6 C7 H7 125.1 . . ?
C6 N5 N4 102.7(4) . . ?
C7 N4 N5 110.5(3) . . ?
C7 N4 C5 129.2(4) . . ?
N5 N4 C5 120.3(3) . . ?
N4 C5 C4 111.0(3) . . ?
N4 C5 H5A 109.4 . . ?
C4 C5 H5A 109.4 . . ?
N4 C5 H5B 109.4 . . ?
C4 C5 H5B 109.4 . . ?
H5A C5 H5B 108.0 . . ?
C5 C4 C3 110.6(3) . . ?
C5 C4 H4A 109.5 . . ?
C3 C4 H4A 109.5 . . ?
C5 C4 H4B 109.5 . . ?
C3 C4 H4B 109.5 . . ?
H4A C4 H4B 108.1 . . ?
N6 Cu1 N1 166.87(13) 1_545 . ?
N6 Cu1 N7 88.38(14) 1_545 . ?
N1 Cu1 N7 90.94(15) . . ?
N6 Cu1 N12 89.85(14) 1_545 1_556 ?
N1 Cu1 N12 89.85(14) . 1_556 ?
N7 Cu1 N12 175.55(14) . 1_556 ?
N6 Cu1 O2 97.49(13) 1_545 . ?
N1 Cu1 O2 95.65(12) . . ?
N7 Cu1 O2 93.35(15) . . ?
N12 Cu1 O2 90.93(16) 1_556 . ?
N6 Cu1 O1 84.63(12) 1_545 . ?
N1 Cu1 O1 82.26(12) . . ?
N7 Cu1 O1 90.68(19) . . ?
N12 Cu1 O1 85.08(18) 1_556 . ?
O2 Cu1 O1 175.49(19) . . ?
N2 C1 N1 114.2(4) . . ?
N2 C1 H1 122.9 . . ?
N1 C1 H1 122.9 . . ?
N3 C2 N1 110.2(4) . . ?
N3 C2 H2 124.9 . . ?
N1 C2 H2 124.9 . . ?
N3 C3 C4 111.0(3) . . ?
N3 C3 H3A 109.4 . . ?
C4 C3 H3A 109.4 . . ?
N3 C3 H3B 109.4 . . ?
C4 C3 H3B 109.4 . . ?
H3A C3 H3B 108.0 . . ?
N7 C8 N9 110.1(4) . . ?
N7 C8 H8 125.0 . . ?
N9 C8 H8 125.0 . . ?
N8 C9 N7 114.3(4) . . ?
N8 C9 H9 122.8 . . ?
N7 C9 H9 122.8 . . ?
N9 C10 C11 110.9(3) . . ?
N9 C10 H10A 109.5 . . ?
C11 C10 H10A 109.5 . . ?
N9 C10 H10B 109.5 . . ?
C11 C10 H10B 109.5 . . ?
H10A C10 H10B 108.0 . . ?
O4' Cl1 O5 139.3(6) . . ?
O4' Cl1 O6 67.2(6) . . ?
O5 Cl1 O6 115.9(4) . . ?
O4' Cl1 O6' 114.7(6) . . ?
O5 Cl1 O6' 94.5(8) . . ?
O6 Cl1 O6' 54.8(7) . . ?
O4' Cl1 O3 101.6(6) . . ?
O5 Cl1 O3 112.8(4) . . ?
O6 Cl1 O3 111.2(4) . . ?
O6' Cl1 O3 76.3(7) . . ?
O4' Cl1 O5' 112.1(6) . . ?
O5 Cl1 O5' 28.2(5) . . ?
O6 Cl1 O5' 102.6(6) . . ?
O6' Cl1 O5' 107.6(6) . . ?
O3 Cl1 O5' 139.4(5) . . ?
O4' Cl1 O3' 110.5(6) . . ?
O5 Cl1 O3' 85.1(7) . . ?
O6 Cl1 O3' 151.1(7) . . ?
O6' Cl1 O3' 106.8(6) . . ?
O3 Cl1 O3' 40.0(6) . . ?
O5' Cl1 O3' 104.6(5) . . ?
O4' Cl1 O4 39.7(6) . . ?
O5 Cl1 O4 108.4(5) . . ?
O6 Cl1 O4 103.3(4) . . ?
O6' Cl1 O4 154.3(7) . . ?
O3 Cl1 O4 104.0(4) . . ?
O5' Cl1 O4 89.0(6) . . ?
O3' Cl1 O4 86.9(6) . . ?
O9 Cl2 O10 111.4(3) . . ?
O9 Cl2 O8 110.9(4) . . ?
O10 Cl2 O8 109.9(3) . . ?
O9 Cl2 O7 109.1(3) . . ?
O10 Cl2 O7 110.9(3) . . ?
O8 Cl2 O7 104.6(3) . . ?
C2 N1 C1 102.8(4) . . ?
C2 N1 Cu1 127.1(3) . . ?
C1 N1 Cu1 129.9(3) . . ?
C1 N2 N3 102.6(3) . . ?
C2 N3 N2 110.2(3) . . ?
C2 N3 C3 128.6(4) . . ?
N2 N3 C3 121.1(3) . . ?
C8 N7 C9 103.6(4) . . ?
C8 N7 Cu1 129.0(3) . . ?
C9 N7 Cu1 127.2(3) . . ?
C9 N8 N9 102.4(3) . . ?
C8 N9 N8 109.6(4) . . ?
C8 N9 C10 130.4(4) . . ?
N8 N9 C10 120.0(4) . . ?
Cu1 O1 H1A 123.4 . . ?
Cu1 O1 H1B 113.9 . . ?
H1A O1 H1B 114.3 . . ?
Cu1 O2 H2A 115.6 . . ?
Cu1 O2 H2B 128.6 . . ?
H2A O2 H2B 114.8 . . ?
H11C O11 H11D 113.2 . . ?
H12C O12 H12D 114.1 . . ?

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
C13 N12 C14 N10 -0.2(5) . . . . ?
Cu1 N12 C14 N10 -171.5(3) 1_554 . . . ?
C14 N12 C13 N11 -0.1(5) . . . . ?
Cu1 N12 C13 N11 170.9(3) 1_554 . . . ?
N12 C13 N11 N10 0.3(5) . . . . ?
N12 C14 N10 N11 0.4(5) . . . . ?
N12 C14 N10 C12 171.2(4) . . . . ?
C13 N11 N10 C14 -0.4(5) . . . . ?
C13 N11 N10 C12 -172.0(4) . . . . ?
C14 N10 C12 C11 137.8(5) . . . . ?
N11 N10 C12 C11 -52.4(6) . . . . ?
N10 C12 C11 C10 -69.0(5) . . . . ?
C7 N6 C6 N5 0.3(6) . . . . ?
Cu1 N6 C6 N5 176.4(3) 1_565 . . . ?
C6 N6 C7 N4 -0.1(5) . . . . ?
Cu1 N6 C7 N4 -176.3(3) 1_565 . . . ?
N6 C6 N5 N4 -0.4(6) . . . . ?
N6 C7 N4 N5 -0.2(5) . . . . ?
N6 C7 N4 C5 178.4(4) . . . . ?
C6 N5 N4 C7 0.3(5) . . . . ?
C6 N5 N4 C5 -178.3(4) . . . . ?
C7 N4 C5 C4 124.0(5) . . . . ?
N5 N4 C5 C4 -57.6(6) . . . . ?
N4 C5 C4 C3 -172.0(5) . . . . ?
C5 C4 C3 N3 -173.5(4) . . . . ?
C12 C11 C10 N9 178.1(4) . . . . ?
N3 C2 N1 C1 0.0(5) . . . . ?
N3 C2 N1 Cu1 -175.8(3) . . . . ?
N2 C1 N1 C2 0.0(5) . . . . ?
N2 C1 N1 Cu1 175.6(3) . . . . ?
N6 Cu1 N1 C2 40.3(9) 1_545 . . . ?
N7 Cu1 N1 C2 127.2(4) . . . . ?
N12 Cu1 N1 C2 -48.4(4) 1_556 . . . ?
O2 Cu1 N1 C2 -139.3(4) . . . . ?
O1 Cu1 N1 C2 36.7(4) . . . . ?
N6 Cu1 N1 C1 -134.3(7) 1_545 . . . ?
N7 Cu1 N1 C1 -47.4(4) . . . . ?
N12 Cu1 N1 C1 137.0(4) 1_556 . . . ?
O2 Cu1 N1 C1 46.1(4) . . . . ?
O1 Cu1 N1 C1 -137.9(4) . . . . ?
N1 C1 N2 N3 0.1(5) . . . . ?
N1 C2 N3 N2 0.1(5) . . . . ?
N1 C2 N3 C3 176.2(4) . . . . ?
C1 N2 N3 C2 -0.1(5) . . . . ?
C1 N2 N3 C3 -176.6(4) . . . . ?
C4 C3 N3 C2 122.6(6) . . . . ?
C4 C3 N3 N2 -61.6(6) . . . . ?
N9 C8 N7 C9 0.9(5) . . . . ?
N9 C8 N7 Cu1 -174.3(3) . . . . ?
N8 C9 N7 C8 -0.9(5) . . . . ?
N8 C9 N7 Cu1 174.5(3) . . . . ?
N6 Cu1 N7 C8 121.4(4) 1_545 . . . ?
N1 Cu1 N7 C8 -45.4(4) . . . . ?
N12 Cu1 N7 C8 55(2) 1_556 . . . ?
O2 Cu1 N7 C8 -141.2(4) . . . . ?
O1 Cu1 N7 C8 36.8(4) . . . . ?
N6 Cu1 N7 C9 -52.7(4) 1_545 . . . ?
N1 Cu1 N7 C9 140.4(4) . . . . ?
N12 Cu1 N7 C9 -119.4(18) 1_556 . . . ?
O2 Cu1 N7 C9 44.7(4) . . . . ?
O1 Cu1 N7 C9 -137.3(4) . . . . ?
N7 C9 N8 N9 0.5(5) . . . . ?
N7 C8 N9 N8 -0.6(5) . . . . ?
N7 C8 N9 C10 177.1(4) . . . . ?
C9 N8 N9 C8 0.1(5) . . . . ?
C9 N8 N9 C10 -177.9(4) . . . . ?
C11 C10 N9 C8 30.5(6) . . . . ?
C11 C10 N9 N8 -152.0(4) . . . . ?

_diffrn_measured_fraction_theta_max 0.999
_diffrn_reflns_theta_full        25.01
_diffrn_measured_fraction_theta_full 0.999
_refine_diff_density_max         0.435
_refine_diff_density_min         -0.492
_refine_diff_density_rms         0.069