# Electronic Supplementary Material (ESI) for RSC Advances.
# This journal is © The Royal Society of Chemistry 2015

####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_(complex-1)
_database_code_depnum_ccdc_archive 'CCDC 1060158'
_audit_update_record             
;
2015-04-17 deposited with the CCDC.
2015-07-24 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
 ?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C11 H18 Cu N3 O2, Cl O4'
_chemical_formula_sum            'C11 H18 Cl Cu N3 O6'
_chemical_formula_weight         387.27

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
Cu Cu 0.3201 1.2651 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
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'
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'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_symmetry_cell_setting           Monoclinic
_symmetry_space_group_name_H-M   'P 21/c'

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                   9.9206(3)
_cell_length_b                   14.4822(4)
_cell_length_c                   10.9734(3)
_cell_angle_alpha                90.00
_cell_angle_beta                 100.5371(15)
_cell_angle_gamma                90.00
_cell_volume                     1549.98(8)
_cell_formula_units_Z            4
_cell_measurement_temperature    295
_cell_measurement_reflns_used    7961
_cell_measurement_theta_min      3.78
_cell_measurement_theta_max      30.05

_exptl_crystal_description       prismatic
_exptl_crystal_colour            'dark red'
_exptl_crystal_size_max          0.30
_exptl_crystal_size_mid          0.26
_exptl_crystal_size_min          0.16
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.660
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             796
_exptl_absorpt_coefficient_mu    1.613
_exptl_absorpt_correction_type   empirical
_exptl_absorpt_correction_T_min  0.643
_exptl_absorpt_correction_T_max  0.790
_exptl_absorpt_process_details   
'SORTAV (R.H Blessing, Acta Crystallogr., 1995, A51, 33)'

_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  'Nonius Kappa CCD'
_diffrn_measurement_method       'φ scans and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            7961
_diffrn_reflns_av_R_equivalents  0.0212
_diffrn_reflns_av_sigmaI/netI    0.0358
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_k_min       -20
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_theta_min         3.78
_diffrn_reflns_theta_max         30.05
_reflns_number_total             4510
_reflns_number_gt                3418
_reflns_threshold_expression     I>2sigma(I)

_computing_data_collection       'COLLECT (Nonius, 1998)'
_computing_cell_refinement       'Denzo-SMN (Otwinowski & Minor, 1997)'
_computing_data_reduction        'Denzo-SMN (Otwinowski & Minor, 1997)'
_computing_structure_solution    'SIR97 (Altomare et al., 1999)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    'ORTEPIII (Burnett & Johnson, 1996)'
_computing_publication_material  
'SHELXL-97 (Sheldrick, 1997), PARST (Nardelli, 1995)'

_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)+(0.0708P)²+0.7108P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   difmao
_refine_ls_hydrogen_treatment    refall
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         4510
_refine_ls_number_parameters     271
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0648
_refine_ls_R_factor_gt           0.0453
_refine_ls_wR_factor_ref         0.1308
_refine_ls_wR_factor_gt          0.1188
_refine_ls_goodness_of_fit_ref   1.017
_refine_ls_restrained_S_all      1.017
_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 0.17380(3) 0.42482(2) 0.14850(3) 0.04173(12) Uani 1 1 d . . .
O1 O 0.13860(18) 0.39185(15) -0.02409(16) 0.0513(4) Uani 1 1 d . . .
C1 C 0.2320(3) 0.37015(17) -0.0914(2) 0.0437(5) Uani 1 1 d . . .
C2 C 0.1853(3) 0.3405(2) -0.2148(2) 0.0527(6) Uani 1 1 d . . .
C3 C 0.2760(4) 0.3188(2) -0.2919(3) 0.0633(8) Uani 1 1 d . . .
C4 C 0.4161(4) 0.3246(2) -0.2496(3) 0.0685(9) Uani 1 1 d . . .
C5 C 0.4639(3) 0.3513(2) -0.1298(3) 0.0591(7) Uani 1 1 d . . .
C6 C 0.3741(3) 0.37395(17) -0.0478(2) 0.0463(6) Uani 1 1 d . . .
C7 C 0.4364(3) 0.39600(19) 0.0787(3) 0.0485(6) Uani 1 1 d . . .
N1 N 0.3713(2) 0.41669(14) 0.1649(2) 0.0453(5) Uani 1 1 d . . .
C8 C 0.4435(3) 0.4339(2) 0.2923(3) 0.0573(7) Uani 1 1 d . . .
C9 C 0.3514(3) 0.4046(2) 0.3802(3) 0.0536(7) Uani 1 1 d . . .
N2 N 0.2134(3) 0.44213(18) 0.3331(2) 0.0472(5) Uani 1 1 d . . .
C10 C 0.0979(4) 0.4036(2) 0.3833(3) 0.0575(7) Uani 1 1 d . . .
C11 C -0.0319(4) 0.4335(3) 0.2995(3) 0.0599(8) Uani 1 1 d . . .
N3 N -0.0221(3) 0.4108(2) 0.1701(2) 0.0550(6) Uani 1 1 d . . .
O2 O 0.1357(3) 0.58670(17) 0.1183(2) 0.0580(5) Uani 1 1 d . . .
Cl1 Cl -0.23559(7) 0.19347(5) 0.03913(6) 0.05233(18) Uani 1 1 d . . .
O3 O -0.1041(3) 0.1612(4) 0.0773(3) 0.162(2) Uani 1 1 d . . .
O4 O -0.2542(3) 0.2233(2) -0.0877(2) 0.0839(7) Uani 1 1 d . . .
O5 O -0.3332(4) 0.1245(2) 0.0498(3) 0.1161(12) Uani 1 1 d . . .
O6 O -0.2603(5) 0.2689(3) 0.1118(4) 0.1291(14) Uani 1 1 d . . .
H2 H 0.092(3) 0.331(2) -0.238(3) 0.046(8) Uiso 1 1 d . . .
H3 H 0.247(3) 0.302(2) -0.369(3) 0.050(8) Uiso 1 1 d . . .
H4 H 0.466(4) 0.305(3) -0.302(4) 0.085(12) Uiso 1 1 d . . .
H5 H 0.557(4) 0.346(2) -0.097(3) 0.057(9) Uiso 1 1 d . . .
H7 H 0.527(4) 0.394(2) 0.097(3) 0.060(9) Uiso 1 1 d . . .
H81 H 0.539(4) 0.400(3) 0.304(4) 0.083(12) Uiso 1 1 d . . .
H82 H 0.457(4) 0.494(3) 0.294(4) 0.082(12) Uiso 1 1 d . . .
H91 H 0.385(3) 0.4281(17) 0.462(3) 0.040(7) Uiso 1 1 d . . .
H92 H 0.340(3) 0.338(2) 0.378(3) 0.056(8) Uiso 1 1 d . . .
H2N H 0.218(4) 0.493(2) 0.345(3) 0.058(10) Uiso 1 1 d . . .
H101 H 0.113(4) 0.335(3) 0.381(3) 0.070(10) Uiso 1 1 d . . .
H102 H 0.108(4) 0.424(2) 0.460(3) 0.059(9) Uiso 1 1 d . . .
H111 H -0.100(5) 0.406(3) 0.314(4) 0.089(14) Uiso 1 1 d . . .
H112 H -0.037(4) 0.499(3) 0.304(4) 0.084(12) Uiso 1 1 d . . .
H3N1 H -0.042(4) 0.354(3) 0.157(3) 0.063(10) Uiso 1 1 d . . .
H3N2 H -0.077(5) 0.442(3) 0.119(5) 0.100(16) Uiso 1 1 d . . .
H2O1 H 0.062(5) 0.596(3) 0.114(4) 0.086(15) Uiso 1 1 d . . .
H2O2 H 0.175(4) 0.626(3) 0.134(3) 0.062(13) Uiso 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 1.9222(18) . ?
Cu1 N1 1.938(2) . ?
Cu1 N2 2.007(2) . ?
Cu1 N3 2.010(3) . ?
Cu1 O2 2.388(2) . ?
O1 C1 1.324(3) . ?
C1 C6 1.405(4) . ?
C1 C2 1.415(4) . ?
C2 C3 1.380(4) . ?
C2 H2 0.92(3) . ?
C3 C4 1.384(5) . ?
C3 H3 0.88(3) . ?
C4 C5 1.369(5) . ?
C4 H4 0.87(4) . ?
C5 C6 1.416(4) . ?
C5 H5 0.93(3) . ?
C6 C7 1.449(4) . ?
C7 N1 1.275(4) . ?
C7 H7 0.88(3) . ?
N1 C8 1.472(4) . ?
C8 C9 1.506(5) . ?
C8 H81 1.05(4) . ?
C8 H82 0.88(4) . ?
C9 N2 1.476(4) . ?
C9 H91 0.97(3) . ?
C9 H92 0.97(3) . ?
N2 C10 1.469(4) . ?
N2 H2N 0.74(3) . ?
C10 C11 1.503(5) . ?
C10 H101 1.01(4) . ?
C10 H102 0.88(4) . ?
C11 N3 1.478(4) . ?
C11 H111 0.83(4) . ?
C11 H112 0.95(4) . ?
N3 H3N1 0.85(4) . ?
N3 H3N2 0.84(5) . ?
O2 H2O1 0.73(5) . ?
O2 H2O2 0.69(4) . ?
Cl1 O3 1.377(3) . ?
Cl1 O6 1.401(3) . ?
Cl1 O5 1.411(3) . ?
Cl1 O4 1.436(2) . ?

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 N1 94.29(9) . . ?
O1 Cu1 N2 172.77(9) . . ?
N1 Cu1 N2 84.61(10) . . ?
O1 Cu1 N3 94.93(9) . . ?
N1 Cu1 N3 164.90(11) . . ?
N2 Cu1 N3 84.74(10) . . ?
O1 Cu1 O2 96.39(9) . . ?
N1 Cu1 O2 101.78(9) . . ?
N2 Cu1 O2 90.83(10) . . ?
N3 Cu1 O2 89.05(12) . . ?
C1 O1 Cu1 126.10(16) . . ?
O1 C1 C6 124.2(2) . . ?
O1 C1 C2 117.8(2) . . ?
C6 C1 C2 118.0(2) . . ?
C3 C2 C1 121.3(3) . . ?
C3 C2 H2 122.0(18) . . ?
C1 C2 H2 116.4(18) . . ?
C2 C3 C4 120.5(3) . . ?
C2 C3 H3 122(2) . . ?
C4 C3 H3 118(2) . . ?
C5 C4 C3 119.3(3) . . ?
C5 C4 H4 126(3) . . ?
C3 C4 H4 114(3) . . ?
C4 C5 C6 121.9(3) . . ?
C4 C5 H5 119(2) . . ?
C6 C5 H5 118(2) . . ?
C1 C6 C5 118.9(3) . . ?
C1 C6 C7 124.1(2) . . ?
C5 C6 C7 116.9(3) . . ?
N1 C7 C6 125.3(2) . . ?
N1 C7 H7 118(2) . . ?
C6 C7 H7 117(2) . . ?
C7 N1 C8 121.3(2) . . ?
C7 N1 Cu1 125.93(19) . . ?
C8 N1 Cu1 112.7(2) . . ?
N1 C8 C9 108.3(2) . . ?
N1 C8 H81 108(2) . . ?
C9 C8 H81 115(2) . . ?
N1 C8 H82 104(3) . . ?
C9 C8 H82 112(3) . . ?
H81 C8 H82 109(3) . . ?
N2 C9 C8 107.7(2) . . ?
N2 C9 H91 109.9(17) . . ?
C8 C9 H91 110.5(17) . . ?
N2 C9 H92 104.8(19) . . ?
C8 C9 H92 110.3(18) . . ?
H91 C9 H92 113(2) . . ?
C10 N2 C9 117.7(2) . . ?
C10 N2 Cu1 108.02(19) . . ?
C9 N2 Cu1 107.79(17) . . ?
C10 N2 H2N 110(3) . . ?
C9 N2 H2N 106(3) . . ?
Cu1 N2 H2N 107(3) . . ?
N2 C10 C11 107.5(2) . . ?
N2 C10 H101 104(2) . . ?
C11 C10 H101 112(2) . . ?
N2 C10 H102 106(2) . . ?
C11 C10 H102 115(2) . . ?
H101 C10 H102 111(3) . . ?
N3 C11 C10 108.9(3) . . ?
N3 C11 H111 106(3) . . ?
C10 C11 H111 112(3) . . ?
N3 C11 H112 106(2) . . ?
C10 C11 H112 108(3) . . ?
H111 C11 H112 115(4) . . ?
C11 N3 Cu1 109.1(2) . . ?
C11 N3 H3N1 109(2) . . ?
Cu1 N3 H3N1 106(2) . . ?
C11 N3 H3N2 112(3) . . ?
Cu1 N3 H3N2 113(3) . . ?
H3N1 N3 H3N2 108(4) . . ?
Cu1 O2 H2O1 109(3) . . ?
Cu1 O2 H2O2 135(3) . . ?
H2O1 O2 H2O2 112(4) . . ?
O3 Cl1 O6 110.3(3) . . ?
O3 Cl1 O5 111.2(3) . . ?
O6 Cl1 O5 108.1(3) . . ?
O3 Cl1 O4 110.1(2) . . ?
O6 Cl1 O4 108.2(2) . . ?
O5 Cl1 O4 108.92(19) . . ?

_diffrn_measured_fraction_theta_max 0.992
_diffrn_reflns_theta_full        30.05
_diffrn_measured_fraction_theta_full 0.992
_refine_diff_density_max         0.740
_refine_diff_density_min         -0.466
_refine_diff_density_rms         0.069
####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_(complex-2)
_database_code_depnum_ccdc_archive 'CCDC 1060159'
_audit_update_record             
;
2015-04-17 deposited with the CCDC.
2015-07-24 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
 ?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C12 H20 Cu N3 O3, Cl O4'
_chemical_formula_sum            'C12 H20 Cl Cu N3 O7'
_chemical_formula_weight         417.30

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           Trigonal
_symmetry_space_group_name_H-M   P3(1)21

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

_cell_length_a                   12.3073(5)
_cell_length_b                   12.3073(5)
_cell_length_c                   19.1117(6)
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                120.00
_cell_volume                     2507.01(16)
_cell_formula_units_Z            6
_cell_measurement_temperature    295
_cell_measurement_reflns_used    6550
_cell_measurement_theta_min      3.82
_cell_measurement_theta_max      27.00

_exptl_crystal_description       needle
_exptl_crystal_colour            blue
_exptl_crystal_size_max          0.45
_exptl_crystal_size_mid          0.03
_exptl_crystal_size_min          0.025
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.658
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1290
_exptl_absorpt_coefficient_mu    1.507
_exptl_absorpt_correction_type   empirical
_exptl_absorpt_correction_T_min  0.935
_exptl_absorpt_correction_T_max  0.972
_exptl_absorpt_process_details   
'SORTAV (R.H. Blessing, Acta Crystallogr., 1995, A51, 33)'

_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  'Nonius Kappa CCD'
_diffrn_measurement_method       'φ scans and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            6550
_diffrn_reflns_av_R_equivalents  0.0307
_diffrn_reflns_av_sigmaI/netI    0.0585
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_limit_l_max       24
_diffrn_reflns_theta_min         3.82
_diffrn_reflns_theta_max         27.00
_reflns_number_total             3625
_reflns_number_gt                2860
_reflns_threshold_expression     I>2sigma(I)

_computing_data_collection       'COLLECT (Nonius, 1998)'
_computing_cell_refinement       'Denzo-SMN (Otwinowski & Minor, 1997)'
_computing_data_reduction        'Denzo-SMN (Otwinowski & Minor, 1997)'
_computing_structure_solution    'SIR97 (Altomare et al., 1999)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    'ORTEP III (Burnett & Johnson, 1996)'
_computing_publication_material  
'SHELXL-97 (Sheldrick, 1997), PARST (Nardelli, 1995)'

_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)+(0.0638P)²+0.1514P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   difmap
_refine_ls_hydrogen_treatment    mixed
_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   0.031(19)
_refine_ls_number_reflns         3625
_refine_ls_number_parameters     273
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0643
_refine_ls_R_factor_gt           0.0433
_refine_ls_wR_factor_ref         0.1101
_refine_ls_wR_factor_gt          0.0995
_refine_ls_goodness_of_fit_ref   1.022
_refine_ls_restrained_S_all      1.022
_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 0.86652(5) 0.08262(4) 0.43763(2) 0.04122(16) Uani 1 1 d . . .
O1 O 0.8148(3) -0.0860(3) 0.41132(14) 0.0438(6) Uani 1 1 d . . .
C1 C 0.6979(4) -0.1786(4) 0.41150(18) 0.0401(9) Uani 1 1 d . . .
C2 C 0.6778(4) -0.3018(4) 0.40756(17) 0.0441(9) Uani 1 1 d . . .
C3 C 0.5572(5) -0.4058(5) 0.4090(2) 0.0592(13) Uani 1 1 d . . .
H3 H 0.550(5) -0.485(5) 0.407(2) 0.069(16) Uiso 1 1 d . . .
C4 C 0.4528(5) -0.3881(6) 0.4115(2) 0.0703(15) Uani 1 1 d . . .
H4 H 0.367(4) -0.465(4) 0.405(2) 0.046(12) Uiso 1 1 d . . .
C5 C 0.4689(4) -0.2720(6) 0.4132(2) 0.0616(14) Uani 1 1 d . . .
H5 H 0.395(5) -0.254(5) 0.411(2) 0.065(14) Uiso 1 1 d . . .
C6 C 0.5913(4) -0.1632(4) 0.4144(2) 0.0472(10) Uani 1 1 d . . .
C7 C 0.5985(4) -0.0442(5) 0.4243(2) 0.0535(11) Uani 1 1 d . . .
H7 H 0.511(5) -0.052(5) 0.422(2) 0.055(12) Uiso 1 1 d . . .
N1 N 0.6985(4) 0.0584(4) 0.43646(17) 0.0497(9) Uani 1 1 d . . .
C8 C 0.6953(6) 0.1747(6) 0.4536(3) 0.0658(14) Uani 1 1 d . . .
H8A H 0.6715 0.1729 0.5022 0.079 Uiso 1 1 calc R . .
H8B H 0.6338 0.1804 0.4244 0.079 Uiso 1 1 calc R . .
C9 C 0.8224(5) 0.2854(5) 0.4411(3) 0.0620(13) Uani 1 1 d . . .
H9A H 0.8350 0.3028 0.3913 0.074 Uiso 1 1 calc R . .
H9B H 0.8290 0.3586 0.4642 0.074 Uiso 1 1 calc R . .
N2 N 0.9192(4) 0.2600(4) 0.4682(2) 0.0519(10) Uani 1 1 d . . .
H2N H 0.913(4) 0.256(4) 0.511(2) 0.035(11) Uiso 1 1 d . . .
C10 C 1.0496(5) 0.3456(5) 0.4472(2) 0.0594(12) Uani 1 1 d . . .
H10A H 1.0881 0.4166 0.4789 0.071 Uiso 1 1 calc R . .
H10B H 1.0520 0.3767 0.4003 0.071 Uiso 1 1 calc R . .
C11 C 1.1202(5) 0.2742(5) 0.4494(3) 0.0566(12) Uani 1 1 d . . .
H11A H 1.131(4) 0.253(4) 0.500(2) 0.047(12) Uiso 1 1 d . . .
H11B H 1.186(5) 0.311(5) 0.437(2) 0.046(14) Uiso 1 1 d . . .
N3 N 1.0458(4) 0.1534(4) 0.4117(2) 0.0466(9) Uani 1 1 d . . .
H3N1 H 1.070(4) 0.106(4) 0.422(2) 0.027(10) Uiso 1 1 d . . .
H3N2 H 1.052(6) 0.157(6) 0.371(3) 0.069(18) Uiso 1 1 d . . .
C12 C 0.7765(7) -0.4279(5) 0.4020(3) 0.0671(15) Uani 1 1 d . . .
H12A H 0.869(6) -0.419(6) 0.399(3) 0.079(17) Uiso 1 1 d . . .
H12B H 0.720(5) -0.487(6) 0.359(3) 0.070(14) Uiso 1 1 d . . .
H12C H 0.738(5) -0.465(5) 0.437(3) 0.064(16) Uiso 1 1 d . . .
O7 O 0.7861(3) -0.3067(3) 0.40211(16) 0.0524(8) Uani 1 1 d . . .
O2 O 0.9093(4) 0.0416(4) 0.55553(17) 0.0499(8) Uani 1 1 d . . .
H2W1 H 0.887(4) -0.019(5) 0.559(2) 0.033(14) Uiso 1 1 d . . .
H2W2 H 0.879(7) 0.059(6) 0.589(3) 0.08(2) Uiso 1 1 d . . .
Cl1 Cl 0.76998(16) 0.18433(14) 0.66957(6) 0.0726(4) Uani 1 1 d . . .
O3 O 0.6472(7) 0.1355(10) 0.6338(4) 0.180(4) Uani 1 1 d . . .
O4 O 0.8571(5) 0.2759(5) 0.6215(2) 0.1008(15) Uani 1 1 d . . .
O5 O 0.7557(9) 0.2297(7) 0.7305(3) 0.164(3) Uani 1 1 d . . .
O6 O 0.7970(9) 0.0899(7) 0.6760(3) 0.176(4) 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 1.909(3) . ?
Cu1 N1 1.936(4) . ?
Cu1 N3 1.988(4) . ?
Cu1 N2 2.028(4) . ?
Cu1 O2 2.424(3) . ?
O1 C1 1.316(5) . ?
C1 C2 1.411(6) . ?
C1 C6 1.417(6) . ?
C2 O7 1.368(6) . ?
C2 C3 1.393(6) . ?
C3 C4 1.408(9) . ?
C3 H3 0.94(6) . ?
C4 C5 1.341(9) . ?
C4 H4 1.01(5) . ?
C5 C6 1.430(7) . ?
C5 H5 1.04(6) . ?
C6 C7 1.434(7) . ?
C7 N1 1.269(6) . ?
C7 H7 1.04(5) . ?
N1 C8 1.488(6) . ?
C8 C9 1.493(8) . ?
C8 H8A 0.9700 . ?
C8 H8B 0.9700 . ?
C9 N2 1.469(6) . ?
C9 H9A 0.9700 . ?
C9 H9B 0.9700 . ?
N2 C10 1.468(6) . ?
N2 H2N 0.81(4) . ?
C10 C11 1.514(8) . ?
C10 H10A 0.9700 . ?
C10 H10B 0.9700 . ?
C11 N3 1.485(6) . ?
C11 H11A 1.03(4) . ?
C11 H11B 0.75(5) . ?
N3 H3N1 0.80(5) . ?
N3 H3N2 0.79(6) . ?
C12 O7 1.436(6) . ?
C12 H12A 1.08(6) . ?
C12 H12B 1.08(6) . ?
C12 H12C 0.81(6) . ?
O2 H2W1 0.66(5) . ?
O2 H2W2 0.82(7) . ?
Cl1 O5 1.340(5) . ?
Cl1 O6 1.365(5) . ?
Cl1 O4 1.434(4) . ?
Cl1 O3 1.484(7) . ?

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 N1 94.58(14) . . ?
O1 Cu1 N3 95.98(13) . . ?
N1 Cu1 N3 158.53(18) . . ?
O1 Cu1 N2 178.41(14) . . ?
N1 Cu1 N2 84.90(16) . . ?
N3 Cu1 N2 85.00(16) . . ?
O1 Cu1 O2 90.43(13) . . ?
N1 Cu1 O2 107.76(14) . . ?
N3 Cu1 O2 90.82(17) . . ?
N2 Cu1 O2 88.30(15) . . ?
C1 O1 Cu1 124.5(3) . . ?
O1 C1 C2 117.3(4) . . ?
O1 C1 C6 124.7(4) . . ?
C2 C1 C6 118.0(4) . . ?
O7 C2 C3 125.1(4) . . ?
O7 C2 C1 113.6(4) . . ?
C3 C2 C1 121.3(5) . . ?
C2 C3 C4 119.6(5) . . ?
C2 C3 H3 117(3) . . ?
C4 C3 H3 123(3) . . ?
C5 C4 C3 120.4(5) . . ?
C5 C4 H4 122(3) . . ?
C3 C4 H4 117(3) . . ?
C4 C5 C6 121.6(5) . . ?
C4 C5 H5 123(3) . . ?
C6 C5 H5 115(3) . . ?
C1 C6 C5 119.1(5) . . ?
C1 C6 C7 123.6(4) . . ?
C5 C6 C7 117.2(4) . . ?
N1 C7 C6 125.0(4) . . ?
N1 C7 H7 123(3) . . ?
C6 C7 H7 112(3) . . ?
C7 N1 C8 121.2(4) . . ?
C7 N1 Cu1 125.8(3) . . ?
C8 N1 Cu1 112.9(3) . . ?
N1 C8 C9 108.8(4) . . ?
N1 C8 H8A 109.9 . . ?
C9 C8 H8A 109.9 . . ?
N1 C8 H8B 109.9 . . ?
C9 C8 H8B 109.9 . . ?
H8A C8 H8B 108.3 . . ?
N2 C9 C8 109.9(4) . . ?
N2 C9 H9A 109.7 . . ?
C8 C9 H9A 109.7 . . ?
N2 C9 H9B 109.7 . . ?
C8 C9 H9B 109.7 . . ?
H9A C9 H9B 108.2 . . ?
C10 N2 C9 117.6(4) . . ?
C10 N2 Cu1 109.9(3) . . ?
C9 N2 Cu1 105.7(3) . . ?
C10 N2 H2N 111(3) . . ?
C9 N2 H2N 108(3) . . ?
Cu1 N2 H2N 105(3) . . ?
N2 C10 C11 108.3(4) . . ?
N2 C10 H10A 110.0 . . ?
C11 C10 H10A 110.0 . . ?
N2 C10 H10B 110.0 . . ?
C11 C10 H10B 110.0 . . ?
H10A C10 H10B 108.4 . . ?
N3 C11 C10 108.8(4) . . ?
N3 C11 H11A 108(2) . . ?
C10 C11 H11A 111(2) . . ?
N3 C11 H11B 113(4) . . ?
C10 C11 H11B 114(4) . . ?
H11A C11 H11B 102(4) . . ?
C11 N3 Cu1 108.1(3) . . ?
C11 N3 H3N1 110(3) . . ?
Cu1 N3 H3N1 111(3) . . ?
C11 N3 H3N2 115(4) . . ?
Cu1 N3 H3N2 109(4) . . ?
H3N1 N3 H3N2 103(5) . . ?
O7 C12 H12A 111(4) . . ?
O7 C12 H12B 113(3) . . ?
H12A C12 H12B 109(4) . . ?
O7 C12 H12C 108(4) . . ?
H12A C12 H12C 113(5) . . ?
H12B C12 H12C 104(5) . . ?
C2 O7 C12 118.0(4) . . ?
Cu1 O2 H2W1 109(4) . . ?
Cu1 O2 H2W2 120(4) . . ?
H2W1 O2 H2W2 103(6) . . ?
O5 Cl1 O6 114.6(4) . . ?
O5 Cl1 O4 115.5(4) . . ?
O6 Cl1 O4 108.8(4) . . ?
O5 Cl1 O3 104.5(5) . . ?
O6 Cl1 O3 109.2(6) . . ?
O4 Cl1 O3 103.5(4) . . ?

_diffrn_measured_fraction_theta_max 0.991
_diffrn_reflns_theta_full        27.00
_diffrn_measured_fraction_theta_full 0.991
_refine_diff_density_max         0.431
_refine_diff_density_min         -0.432
_refine_diff_density_rms         0.064
####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_(complex-3)
_database_code_depnum_ccdc_archive 'CCDC 1060160'
_audit_update_record             
;
2015-04-17 deposited with the CCDC.
2015-07-24 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
 ?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C12 H20 Cu N3 O2, Cl O4'
_chemical_formula_sum            'C12 H20 Cl Cu N3 O6'
_chemical_formula_weight         401.30

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
Cu Cu 0.3201 1.2651 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
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'
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'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_H-M   'P 21/c'

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                   10.0150(10)
_cell_length_b                   14.9210(10)
_cell_length_c                   11.0160(10)
_cell_angle_alpha                90.00
_cell_angle_beta                 107.720(10)
_cell_angle_gamma                90.00
_cell_volume                     1568.1(2)
_cell_formula_units_Z            4
_cell_measurement_temperature    295
_cell_measurement_reflns_used    12909
_cell_measurement_theta_min      2.13
_cell_measurement_theta_max      26.00

_exptl_crystal_description       block
_exptl_crystal_colour            brown
_exptl_crystal_size_max          0.40
_exptl_crystal_size_mid          0.28
_exptl_crystal_size_min          0.23
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.700
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             828
_exptl_absorpt_coefficient_mu    1.597
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.603
_exptl_absorpt_correction_T_max  0.712
_exptl_absorpt_process_details   
'SORTAV (R.H. Blessing, Acta Cryst., 1995, A51, 33)'

_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      295
_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  'Nonius Kappa CCD'
_diffrn_measurement_method       'φ scans and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            12909
_diffrn_reflns_av_R_equivalents  0.0379
_diffrn_reflns_av_sigmaI/netI    0.0338
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_k_min       -18
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_theta_min         2.13
_diffrn_reflns_theta_max         26.00
_reflns_number_total             3063
_reflns_number_gt                2324
_reflns_threshold_expression     I>2sigma(I)

_computing_data_collection       'COLLECT (Nonius, 1998)'
_computing_cell_refinement       'Denzo-SMN (Otwinowski & Minor, 1997)'
_computing_data_reduction        'Denzo-SMN (Otwinowski & Minor, 1997)'
_computing_structure_solution    'SIR97 (Altomare et al., 1999)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    'ORTEPIII (Burnett & Johnson, 1996)'
_computing_publication_material  
'SHELXL-97 (Sheldrick, 1997), PARST (Nardelli, 1995)'

_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)+(0.0787P)²+1.4119P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         3063
_refine_ls_number_parameters     229
_refine_ls_number_restraints     5
_refine_ls_R_factor_all          0.0657
_refine_ls_R_factor_gt           0.0472
_refine_ls_wR_factor_ref         0.1409
_refine_ls_wR_factor_gt          0.1279
_refine_ls_goodness_of_fit_ref   1.051
_refine_ls_restrained_S_all      1.050
_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 0.32467(5) 0.41787(3) 0.35341(4) 0.03826(19) Uani 1 1 d . . .
O1 O 0.3545(3) 0.3992(2) 0.5268(3) 0.0482(7) Uani 1 1 d . . .
C1 C 0.2610(4) 0.3746(3) 0.5877(4) 0.0406(9) Uani 1 1 d . . .
C2 C 0.3090(5) 0.3491(3) 0.7137(4) 0.0488(11) Uani 1 1 d . . .
H2 H 0.4055 0.3477 0.7524 0.059 Uiso 1 1 calc R . .
C3 C 0.2227(6) 0.3250(3) 0.7885(4) 0.0565(12) Uani 1 1 d . . .
H3 H 0.2641 0.3091 0.8733 0.068 Uiso 1 1 calc R . .
C4 C 0.0825(6) 0.3244(3) 0.7406(5) 0.0611(13) Uani 1 1 d . . .
H4 H 0.0245 0.3088 0.7890 0.073 Uiso 1 1 calc R . .
C5 C 0.0330(5) 0.3477(3) 0.6198(4) 0.0525(11) Uani 1 1 d . . .
H5 H -0.0638 0.3478 0.5834 0.063 Uiso 1 1 calc R . .
C6 C 0.1173(4) 0.3733(3) 0.5389(4) 0.0381(9) Uani 1 1 d . . .
C7 C 0.0531(4) 0.3967(2) 0.4082(4) 0.0392(9) Uani 1 1 d . . .
C8 C -0.1000(4) 0.4025(3) 0.3699(5) 0.0568(12) Uani 1 1 d . . .
H8A H -0.1319 0.4445 0.3011 0.085 Uiso 1 1 calc R . .
H8B H -0.1290 0.4222 0.4410 0.085 Uiso 1 1 calc R . .
H8C H -0.1396 0.3446 0.3425 0.085 Uiso 1 1 calc R . .
N1 N 0.1260(3) 0.4100(2) 0.3270(3) 0.0410(8) Uani 1 1 d . . .
C9 C 0.0616(5) 0.4285(3) 0.1952(4) 0.0542(12) Uani 1 1 d . . .
H9A H 0.0444 0.4924 0.1833 0.065 Uiso 1 1 calc R . .
H9B H -0.0279 0.3978 0.1659 0.065 Uiso 1 1 calc R . .
C10 C 0.1571(4) 0.3971(3) 0.1148(4) 0.0526(12) Uani 1 1 d . . .
H10A H 0.1588 0.3322 0.1121 0.063 Uiso 1 1 calc R . .
H10B H 0.1197 0.4191 0.0282 0.063 Uiso 1 1 calc R . .
N2 N 0.2950(4) 0.4303(2) 0.1700(3) 0.0437(8) Uani 1 1 d D . .
H2N H 0.292(4) 0.4885(10) 0.149(4) 0.039(11) Uiso 1 1 d D . .
N3 N 0.5238(4) 0.4025(3) 0.3473(4) 0.0505(10) Uani 1 1 d D . .
H1N3 H 0.567(5) 0.448(2) 0.399(4) 0.062(15) Uiso 1 1 d D . .
H2N3 H 0.545(5) 0.3450(12) 0.368(4) 0.058(15) Uiso 1 1 d D . .
C11 C 0.4100(5) 0.3890(3) 0.1295(4) 0.0513(11) Uani 1 1 d . . .
H11A H 0.4030 0.3242 0.1300 0.062 Uiso 1 1 calc R . .
H11B H 0.4043 0.4083 0.0439 0.062 Uiso 1 1 calc R . .
C12 C 0.5394(5) 0.4179(4) 0.2182(4) 0.0540(12) Uani 1 1 d . . .
H12A H 0.5558 0.4808 0.2059 0.065 Uiso 1 1 calc R . .
H12B H 0.6172 0.3833 0.2077 0.065 Uiso 1 1 calc R . .
O2 O 0.3663(4) 0.5808(2) 0.3733(3) 0.0543(8) Uani 1 1 d D . .
H1O2 H 0.307(6) 0.629(3) 0.334(6) 0.10(2) Uiso 1 1 d D . .
H2O2 H 0.458(3) 0.594(4) 0.371(6) 0.09(2) Uiso 1 1 d D . .
Cl1 Cl 0.28159(11) 0.67260(8) 0.04665(11) 0.0517(3) Uani 1 1 d . . .
O3 O 0.3496(9) 0.5946(3) 0.0347(6) 0.153(3) Uani 1 1 d . . .
O4 O 0.3464(10) 0.7199(4) 0.1493(7) 0.216(5) Uani 1 1 d . . .
O5 O 0.1607(7) 0.6484(6) 0.0783(8) 0.176(3) Uani 1 1 d . . .
O6 O 0.2540(6) 0.7247(3) -0.0612(5) 0.1144(18) 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 1.862(3) . ?
Cu1 N1 1.924(3) . ?
Cu1 N2 1.960(3) . ?
Cu1 N3 2.029(4) . ?
O1 C1 1.358(5) . ?
C1 C6 1.375(6) . ?
C1 C2 1.377(6) . ?
C2 C3 1.410(7) . ?
C2 H2 0.9300 . ?
C3 C4 1.341(7) . ?
C3 H3 0.9300 . ?
C4 C5 1.317(7) . ?
C4 H4 0.9300 . ?
C5 C6 1.454(6) . ?
C5 H5 0.9300 . ?
C6 C7 1.430(6) . ?
C7 N1 1.331(6) . ?
C7 C8 1.464(5) . ?
C8 H8A 0.9600 . ?
C8 H8B 0.9600 . ?
C8 H8C 0.9600 . ?
N1 C9 1.425(5) . ?
C9 C10 1.559(7) . ?
C9 H9A 0.9700 . ?
C9 H9B 0.9700 . ?
C10 N2 1.419(5) . ?
C10 H10A 0.9700 . ?
C10 H10B 0.9700 . ?
N2 C11 1.489(6) . ?
N2 H2N 0.896(10) . ?
N3 C12 1.495(6) . ?
N3 H1N3 0.905(10) . ?
N3 H2N3 0.897(10) . ?
C11 C12 1.432(6) . ?
C11 H11A 0.9700 . ?
C11 H11B 0.9700 . ?
C12 H12A 0.9700 . ?
C12 H12B 0.9700 . ?
O2 H1O2 0.947(10) . ?
O2 H2O2 0.945(10) . ?
Cl1 O4 1.323(6) . ?
Cl1 O6 1.375(4) . ?
Cl1 O3 1.375(4) . ?
Cl1 O5 1.406(6) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
O1 Cu1 N1 88.96(14) . . ?
O1 Cu1 N2 176.80(15) . . ?
N1 Cu1 N2 91.41(15) . . ?
O1 Cu1 N3 99.49(14) . . ?
N1 Cu1 N3 165.81(15) . . ?
N2 Cu1 N3 79.53(15) . . ?
C1 O1 Cu1 128.9(2) . . ?
O1 C1 C6 127.4(4) . . ?
O1 C1 C2 119.4(4) . . ?
C6 C1 C2 113.1(4) . . ?
C1 C2 C3 124.8(4) . . ?
C1 C2 H2 117.6 . . ?
C3 C2 H2 117.6 . . ?
C4 C3 C2 121.8(5) . . ?
C4 C3 H3 119.1 . . ?
C2 C3 H3 119.1 . . ?
C5 C4 C3 115.0(5) . . ?
C5 C4 H4 122.5 . . ?
C3 C4 H4 122.5 . . ?
C4 C5 C6 125.4(5) . . ?
C4 C5 H5 117.3 . . ?
C6 C5 H5 117.3 . . ?
C1 C6 C7 119.1(4) . . ?
C1 C6 C5 119.9(4) . . ?
C7 C6 C5 121.0(4) . . ?
N1 C7 C6 122.9(4) . . ?
N1 C7 C8 122.6(4) . . ?
C6 C7 C8 114.5(4) . . ?
C7 C8 H8A 109.5 . . ?
C7 C8 H8B 109.5 . . ?
H8A C8 H8B 109.5 . . ?
C7 C8 H8C 109.5 . . ?
H8A C8 H8C 109.5 . . ?
H8B C8 H8C 109.5 . . ?
C7 N1 C9 122.9(3) . . ?
C7 N1 Cu1 131.3(3) . . ?
C9 N1 Cu1 105.6(3) . . ?
N1 C9 C10 110.8(4) . . ?
N1 C9 H9A 109.5 . . ?
C10 C9 H9A 109.5 . . ?
N1 C9 H9B 109.5 . . ?
C10 C9 H9B 109.5 . . ?
H9A C9 H9B 108.1 . . ?
N2 C10 C9 109.7(4) . . ?
N2 C10 H10A 109.7 . . ?
C9 C10 H10A 109.7 . . ?
N2 C10 H10B 109.7 . . ?
C9 C10 H10B 109.7 . . ?
H10A C10 H10B 108.2 . . ?
C10 N2 C11 117.9(4) . . ?
C10 N2 Cu1 103.3(3) . . ?
C11 N2 Cu1 112.4(3) . . ?
C10 N2 H2N 106(3) . . ?
C11 N2 H2N 107(3) . . ?
Cu1 N2 H2N 110(3) . . ?
C12 N3 Cu1 113.7(3) . . ?
C12 N3 H1N3 109(3) . . ?
Cu1 N3 H1N3 100(3) . . ?
C12 N3 H2N3 107(3) . . ?
Cu1 N3 H2N3 105(3) . . ?
H1N3 N3 H2N3 122(5) . . ?
C12 C11 N2 107.0(4) . . ?
C12 C11 H11A 110.3 . . ?
N2 C11 H11A 110.3 . . ?
C12 C11 H11B 110.3 . . ?
N2 C11 H11B 110.3 . . ?
H11A C11 H11B 108.6 . . ?
C11 C12 N3 105.6(4) . . ?
C11 C12 H12A 110.6 . . ?
N3 C12 H12A 110.6 . . ?
C11 C12 H12B 110.6 . . ?
N3 C12 H12B 110.6 . . ?
H12A C12 H12B 108.8 . . ?
H1O2 O2 H2O2 108(5) . . ?
O4 Cl1 O6 110.8(4) . . ?
O4 Cl1 O3 113.9(5) . . ?
O6 Cl1 O3 111.8(3) . . ?
O4 Cl1 O5 99.2(6) . . ?
O6 Cl1 O5 113.4(4) . . ?
O3 Cl1 O5 107.2(5) . . ?

_diffrn_measured_fraction_theta_max 0.995
_diffrn_reflns_theta_full        26.00
_diffrn_measured_fraction_theta_full 0.995
_refine_diff_density_max         0.999
_refine_diff_density_min         -0.574
_refine_diff_density_rms         0.082
