# Electronic Supplementary Material (ESI) for New Journal of Chemistry.
# This journal is © The Royal Society of Chemistry and the Centre National de la Recherche Scientifique 2019

####################################################################### 
# 
# 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_shelx
_database_code_depnum_ccdc_archive 'CCDC 1938493'
loop_
_audit_author_name
_audit_author_address
'Oscar Enrique Piro'
;Universidad Nacional de La Plata
Argentina
;
_audit_update_record             
;
2019-07-04 deposited with the CCDC.	2019-11-12 downloaded from the CCDC.
;
_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        
;
6,6'-((1E,1'E)-(ethane-1,2-diylbis(azaneylylidene))bis(methaneylylidene))bis(3-(diethylamino)phenol) 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C24 H34 N4 O2'
_chemical_formula_weight         410.55

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'

_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'
_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   6.0163(5)
_cell_length_b                   7.4951(5)
_cell_length_c                   13.4880(12)
_cell_angle_alpha                105.570(6)
_cell_angle_beta                 100.446(7)
_cell_angle_gamma                93.766(6)
_cell_volume                     571.97(8)
_cell_formula_units_Z            1
_cell_measurement_temperature    297(2)
_cell_measurement_reflns_used    1068
_cell_measurement_theta_min      3.6330
_cell_measurement_theta_max      26.0260
_exptl_crystal_description       fragment
_exptl_crystal_colour            yellow
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.192
_exptl_crystal_F_000             222
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.379
_exptl_crystal_size_mid          0.175
_exptl_crystal_size_min          0.129
_exptl_absorpt_coefficient_mu    0.077
_shelx_estimated_absorpt_T_min   0.971
_shelx_estimated_absorpt_T_max   0.990
_exptl_absorpt_correction_T_min  0.84590
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.38.41 (Rigaku Oxford Diffraction, 2015)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_oxdiff_exptl_absorpt_empirical_full_min 0.888
_oxdiff_exptl_absorpt_empirical_full_max 1.159
_oxdiff_exptl_absorpt_empirical_details 
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      297(2)
_diffrn_source                   'fine-focus sealed X-ray tube'
_diffrn_source_type              'Enhance (Mo) X-ray Source'
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'Xcalibur, Eos, Gemini'
_diffrn_detector                 'CCD plate'
_diffrn_detector_type            Eos
_diffrn_detector_area_resol_mean 16.0604
_diffrn_reflns_number            4408
_diffrn_reflns_av_unetI/netI     0.0419
_diffrn_reflns_av_R_equivalents  0.0245
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_theta_min         3.469
_diffrn_reflns_theta_max         28.804
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.818
_diffrn_measured_fraction_theta_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.818
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.818
_diffrn_reflns_point_group_measured_fraction_full 0.998
_reflns_number_total             2446
_reflns_number_gt                1408
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_computing_data_collection       'CrysAlisPro 1.171.38.41 (Rigaku OD, 2015)'
_computing_cell_refinement       'CrysAlisPro 1.171.38.41 (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.38.41 (Rigaku OD, 2015)'
_computing_structure_solution    'SHELXT (Sheldrick, 2015)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    'ORTEP-3 (Farrugia, 1997)'
_computing_publication_material  'SHELXL-2014/7 (Sheldrick, 2014)'
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0531P)²+0.0271P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   difmap
_refine_ls_hydrogen_treatment    refall
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         2446
_refine_ls_number_parameters     204
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0994
_refine_ls_R_factor_gt           0.0537
_refine_ls_wR_factor_ref         0.1403
_refine_ls_wR_factor_gt          0.1115
_refine_ls_goodness_of_fit_ref   1.022
_refine_ls_restrained_S_all      1.022
_refine_ls_shift/su_max          0.002
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C 0.4907(3) 0.5603(2) 0.85155(13) 0.0462(4) Uani 1 1 d . . . . .
C2 C 0.3377(3) 0.6393(2) 0.78931(14) 0.0463(4) Uani 1 1 d . . . . .
C3 C 0.1272(3) 0.5454(2) 0.73607(15) 0.0475(5) Uani 1 1 d . . . . .
C4 C 0.0556(3) 0.3689(2) 0.74340(13) 0.0454(4) Uani 1 1 d . . . . .
C5 C 0.2105(3) 0.2876(3) 0.80418(15) 0.0541(5) Uani 1 1 d . . . . .
C6 C 0.4201(3) 0.3822(2) 0.85602(15) 0.0547(5) Uani 1 1 d . . . . .
C7 C 0.7133(3) 0.6560(3) 0.90660(15) 0.0526(5) Uani 1 1 d . . . . .
C8 C 1.0082(3) 0.9073(3) 0.96258(18) 0.0615(6) Uani 1 1 d . . . . .
C9 C -0.3114(3) 0.3596(3) 0.62467(16) 0.0561(5) Uani 1 1 d . . . . .
C10 C -0.2359(4) 0.0967(3) 0.7013(2) 0.0646(6) Uani 1 1 d . . . . .
C11 C -0.2587(5) 0.3271(4) 0.5164(2) 0.0780(7) Uani 1 1 d . . . . .
C12 C -0.1585(6) -0.0617(3) 0.6262(3) 0.0911(9) Uani 1 1 d . . . . .
N1 N 0.7814(3) 0.8195(2) 0.90406(12) 0.0578(4) Uani 1 1 d . . . . .
N2 N -0.1594(2) 0.28059(18) 0.69448(12) 0.0523(4) Uani 1 1 d . . . . .
O O 0.3938(3) 0.81154(17) 0.77955(12) 0.0661(4) Uani 1 1 d . . . . .
H1 H 0.540(4) 0.853(3) 0.824(2) 0.104(8) Uiso 1 1 d . . . . .
H3 H 0.032(3) 0.610(2) 0.6923(13) 0.056(5) Uiso 1 1 d . . . . .
H5 H 0.179(3) 0.166(3) 0.8077(14) 0.065(6) Uiso 1 1 d . . . . .
H6 H 0.526(3) 0.325(2) 0.9003(15) 0.062(5) Uiso 1 1 d . . . . .
H7 H 0.817(3) 0.588(3) 0.9517(16) 0.072(6) Uiso 1 1 d . . . . .
H8A H 1.079(3) 0.826(2) 1.0022(15) 0.062(6) Uiso 1 1 d . . . . .
H8B H 1.108(4) 0.918(3) 0.9098(16) 0.076(6) Uiso 1 1 d . . . . .
H9A H -0.474(3) 0.303(2) 0.6184(14) 0.062(5) Uiso 1 1 d . . . . .
H9B H -0.300(3) 0.501(3) 0.6596(15) 0.066(5) Uiso 1 1 d . . . . .
H10A H -0.172(3) 0.096(2) 0.7765(17) 0.065(6) Uiso 1 1 d . . . . .
H10B H -0.411(4) 0.087(3) 0.6872(16) 0.084(7) Uiso 1 1 d . . . . .
H11A H -0.088(5) 0.364(3) 0.5231(19) 0.101(8) Uiso 1 1 d . . . . .
H11B H -0.346(4) 0.398(3) 0.473(2) 0.115(9) Uiso 1 1 d . . . . .
H11C H -0.292(4) 0.189(3) 0.4763(19) 0.105(8) Uiso 1 1 d . . . . .
H12A H 0.014(6) -0.054(4) 0.639(2) 0.136(11) Uiso 1 1 d . . . . .
H12B H -0.219(5) -0.063(4) 0.552(3) 0.133(12) Uiso 1 1 d . . . . .
H12C H -0.222(4) -0.175(4) 0.6361(19) 0.104(8) 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
C1 C6 1.394(2) . ?
C1 C2 1.401(2) . ?
C1 C7 1.445(2) . ?
C2 O 1.3592(19) . ?
C2 C3 1.377(2) . ?
C3 C4 1.399(2) . ?
C4 N2 1.375(2) . ?
C4 C5 1.406(2) . ?
C5 C6 1.371(3) . ?
C7 N1 1.277(2) . ?
C8 N1 1.460(2) . ?
C8 C8 1.503(4) 2_777 ?
C9 N2 1.460(2) . ?
C9 C11 1.510(3) . ?
C10 N2 1.456(2) . ?
C10 C12 1.501(4) . ?

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
C6 C1 C2 116.75(16) . . ?
C6 C1 C7 121.34(16) . . ?
C2 C1 C7 121.89(16) . . ?
O C2 C3 118.10(15) . . ?
O C2 C1 120.62(15) . . ?
C3 C2 C1 121.28(15) . . ?
C2 C3 C4 121.48(16) . . ?
N2 C4 C3 121.02(15) . . ?
N2 C4 C5 121.57(15) . . ?
C3 C4 C5 117.40(16) . . ?
C6 C5 C4 120.39(17) . . ?
C5 C6 C1 122.66(17) . . ?
N1 C7 C1 122.47(18) . . ?
N1 C8 C8 109.9(2) . 2_777 ?
N2 C9 C11 113.99(18) . . ?
N2 C10 C12 114.3(2) . . ?
C7 N1 C8 119.11(17) . . ?
C4 N2 C10 121.58(15) . . ?
C4 N2 C9 120.88(15) . . ?
C10 N2 C9 117.24(16) . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
O H1 N1 0.95(3) 1.72(3) 2.602(2) 153(2) .

_refine_diff_density_max         0.103
_refine_diff_density_min         -0.139
_refine_diff_density_rms         0.031


_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: Methanol'
####################################################################### 
# 
# 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_shelx_CCDC1
_database_code_depnum_ccdc_archive 'CCDC 1938494'
loop_
_audit_author_name
_audit_author_address
'Oscar Enrique Piro'
;Universidad Nacional de La Plata
Argentina
;
_audit_update_record             
;
2019-07-04 deposited with the CCDC.	2019-11-12 downloaded from the CCDC.
;
_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        
"6,6'-((1E,1'E)-(ethane-1,2-diylbis(azaneylylidene))bis(methaneylylidene))bis(3-(diethylamino)phenolato) copper (II) monohydrate"
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C24 H34 Cu N4 O3'
_chemical_formula_weight         490.09

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

_space_group_crystal_system      monoclinic
_space_group_IT_number           15
_space_group_name_H-M_alt        'C 2/c'
_space_group_name_Hall           '-C 2yc'
_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y, -z+1/2'
'x+1/2, y+1/2, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y, z-1/2'
'-x+1/2, -y+1/2, -z'
'x+1/2, -y+1/2, z-1/2'

_cell_length_a                   19.5737(8)
_cell_length_b                   9.8513(4)
_cell_length_c                   12.4452(4)
_cell_angle_alpha                90
_cell_angle_beta                 93.654(3)
_cell_angle_gamma                90
_cell_volume                     2394.88(16)
_cell_formula_units_Z            4
_cell_measurement_temperature    297(2)
_cell_measurement_reflns_used    1855
_cell_measurement_theta_min      4.0870
_cell_measurement_theta_max      28.4560
_exptl_crystal_description       fragment
_exptl_crystal_colour            violet
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.359
_exptl_crystal_F_000             1036
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.541
_exptl_crystal_size_mid          0.257
_exptl_crystal_size_min          0.071
_exptl_absorpt_coefficient_mu    0.944
_shelx_estimated_absorpt_T_min   0.629
_shelx_estimated_absorpt_T_max   0.936
_exptl_absorpt_correction_T_min  0.79070
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.38.41 (Rigaku Oxford Diffraction, 2015)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_oxdiff_exptl_absorpt_empirical_full_min 0.862
_oxdiff_exptl_absorpt_empirical_full_max 1.204
_oxdiff_exptl_absorpt_empirical_details 
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      297(2)
_diffrn_source                   'fine-focus sealed X-ray tube'
_diffrn_source_type              'Enhance (Mo) X-ray Source'
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'Xcalibur, Eos, Gemini'
_diffrn_detector                 'CCD plate'
_diffrn_detector_type            Eos
_diffrn_detector_area_resol_mean 16.0604
_diffrn_reflns_number            4950
_diffrn_reflns_av_unetI/netI     0.0279
_diffrn_reflns_av_R_equivalents  0.0190
_diffrn_reflns_limit_h_min       -26
_diffrn_reflns_limit_h_max       25
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_theta_min         3.281
_diffrn_reflns_theta_max         28.867
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.818
_diffrn_measured_fraction_theta_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.818
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.818
_diffrn_reflns_point_group_measured_fraction_full 0.998
_reflns_number_total             2575
_reflns_number_gt                2273
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_computing_data_collection       'CrysAlisPro 1.171.38.41 (Rigaku OD, 2015)'
_computing_cell_refinement       'CrysAlisPro 1.171.38.41 (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.38.41 (Rigaku OD, 2015)'
_computing_structure_solution    'SHELXT (Sheldrick, 2015)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    'ORTEP-3 (Farrugia, 1997)'
_computing_publication_material  'SHELXL-2014/7 (Sheldrick, 2014)'
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0513P)²+3.8242P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         2575
_refine_ls_number_parameters     151
_refine_ls_number_restraints     2
_refine_ls_R_factor_all          0.0474
_refine_ls_R_factor_gt           0.0406
_refine_ls_wR_factor_ref         0.1098
_refine_ls_wR_factor_gt          0.1035
_refine_ls_goodness_of_fit_ref   1.037
_refine_ls_restrained_S_all      1.037
_refine_ls_shift/su_max          0.044
_refine_ls_shift/su_mean         0.001
# start Validation Reply Form
_vrf_PLAT230_shelx               
;
PROBLEM: Hirshfeld Test Diff for    N2       --C10               8.0 s.u.  
RESPONSE: Probably due to librational displacement of pendant -CH2-CH3 arm
;
# end Validation Reply Form 
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C 0.58471(12) 0.4680(2) 0.48504(18) 0.0336(5) Uani 1 1 d . . . . .
C2 C 0.58399(11) 0.5938(2) 0.42825(17) 0.0328(5) Uani 1 1 d . . . . .
C3 C 0.62028(12) 0.7034(2) 0.47458(18) 0.0362(5) Uani 1 1 d . . . . .
H3 H 0.6199 0.7852 0.4374 0.043 Uiso 1 1 calc R U . . .
C4 C 0.65746(13) 0.6955(3) 0.57531(19) 0.0397(5) Uani 1 1 d . . . . .
C5 C 0.65269(14) 0.5728(3) 0.6334(2) 0.0450(6) Uani 1 1 d . . . . .
H5 H 0.6732 0.5660 0.7027 0.054 Uiso 1 1 calc R U . . .
C6 C 0.61835(13) 0.4648(3) 0.58863(19) 0.0406(5) Uani 1 1 d . . . . .
H6 H 0.6170 0.3849 0.6282 0.049 Uiso 1 1 calc R U . . .
C7 C 0.55477(12) 0.3460(2) 0.44358(18) 0.0359(5) Uani 1 1 d . . . . .
H7 H 0.5567 0.2703 0.4883 0.043 Uiso 1 1 calc R U . . .
C8 C 0.49867(13) 0.1999(2) 0.31110(19) 0.0402(5) Uani 1 1 d . . . . .
H8A H 0.4520 0.1875 0.3312 0.048 Uiso 1 1 calc R U . . .
H8B H 0.5267 0.1271 0.3426 0.048 Uiso 1 1 calc R U . . .
C9 C 0.70249(15) 0.9283(3) 0.5569(2) 0.0544(7) Uani 1 1 d . . . . .
H9A H 0.7046 0.9081 0.4809 0.065 Uiso 1 1 calc R U . . .
H9B H 0.7452 0.9719 0.5810 0.065 Uiso 1 1 calc R U . . .
C10 C 0.74163(17) 0.7867(4) 0.7154(2) 0.0632(8) Uani 1 1 d . . . . .
H10A H 0.7595 0.6949 0.7196 0.076 Uiso 1 1 calc R U . . .
H10B H 0.7801 0.8482 0.7123 0.076 Uiso 1 1 calc R U . . .
C11 C 0.6454(2) 1.0252(4) 0.5704(3) 0.0757(10) Uani 1 1 d . . . . .
H11A H 0.6035 0.9871 0.5396 0.114 Uiso 1 1 calc R U . . .
H11B H 0.6547 1.1090 0.5347 0.114 Uiso 1 1 calc R U . . .
H11C H 0.6412 1.0421 0.6457 0.114 Uiso 1 1 calc R U . . .
C12 C 0.7054(2) 0.8159(5) 0.8135(3) 0.0815(11) Uani 1 1 d . . . . .
H12A H 0.6875 0.9066 0.8098 0.122 Uiso 1 1 calc R U . . .
H12B H 0.7367 0.8074 0.8757 0.122 Uiso 1 1 calc R U . . .
H12C H 0.6685 0.7526 0.8188 0.122 Uiso 1 1 calc R U . . .
N1 N 0.52507(10) 0.33196(19) 0.34857(15) 0.0355(4) Uani 1 1 d . . . . .
N2 N 0.69664(13) 0.8011(2) 0.61546(18) 0.0535(6) Uani 1 1 d . . . . .
O O 0.55004(9) 0.61237(17) 0.33435(12) 0.0409(4) Uani 1 1 d . . . . .
O1W O 0.5000 0.8647(4) 0.2500 0.170(3) Uani 1 2 d DS T P . .
H1W H 0.516(4) 0.8133(18) 0.203(4) 0.204 Uiso 1 1 d D U . . .
Cu Cu 0.5000 0.47828(4) 0.2500 0.03520(15) Uani 1 2 d S T P . .


_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
C1 C6 1.410(3) . ?
C1 C7 1.420(3) . ?
C1 C2 1.426(3) . ?
C2 O 1.320(3) . ?
C2 C3 1.396(3) . ?
C3 C4 1.411(3) . ?
C4 N2 1.369(3) . ?
C4 C5 1.414(4) . ?
C5 C6 1.359(4) . ?
C7 N1 1.291(3) . ?
C8 N1 1.465(3) . ?
C8 C8 1.525(5) 2_655 ?
C9 N2 1.457(4) . ?
C9 C11 1.488(5) . ?
C10 C12 1.479(5) . ?
C10 N2 1.485(4) . ?
N1 Cu 1.9356(19) . ?
O Cu 1.9172(16) . ?
Cu O 1.9172(16) 2_655 ?
Cu N1 1.9356(19) 2_655 ?

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
C6 C1 C7 118.1(2) . . ?
C6 C1 C2 117.5(2) . . ?
C7 C1 C2 124.4(2) . . ?
O C2 C3 118.2(2) . . ?
O C2 C1 123.2(2) . . ?
C3 C2 C1 118.6(2) . . ?
C2 C3 C4 123.0(2) . . ?
N2 C4 C3 121.9(2) . . ?
N2 C4 C5 121.1(2) . . ?
C3 C4 C5 117.0(2) . . ?
C6 C5 C4 120.4(2) . . ?
C5 C6 C1 123.2(2) . . ?
N1 C7 C1 125.1(2) . . ?
N1 C8 C8 106.48(15) . 2_655 ?
N2 C9 C11 114.3(3) . . ?
C12 C10 N2 112.5(3) . . ?
C7 N1 C8 121.0(2) . . ?
C7 N1 Cu 125.58(16) . . ?
C8 N1 Cu 112.93(15) . . ?
C4 N2 C9 122.1(2) . . ?
C4 N2 C10 121.5(2) . . ?
C9 N2 C10 116.1(2) . . ?
C2 O Cu 126.89(15) . . ?
O Cu O 92.89(10) . 2_655 ?
O Cu N1 163.78(8) . 2_655 ?
O Cu N1 93.79(7) 2_655 2_655 ?
O Cu N1 93.79(7) . . ?
O Cu N1 163.78(8) 2_655 . ?
N1 Cu N1 83.74(11) 2_655 . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
O1W H1W O 0.849(10) 2.39(5) 2.847(4) 115(4) 2_655

_refine_diff_density_max         0.745
_refine_diff_density_min         -0.291
_refine_diff_density_rms         0.062


_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: Methanol'
