# Electronic Supplementary Material (ESI) for Metallomics.
# 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_whl-cu-01
_database_code_depnum_ccdc_archive 'CCDC 1036794'
_audit_update_record             
;
2014-12-01 deposited with the CCDC.
2015-04-15 downloaded from the CCDC.
;
_audit_creation_date             2014-09-02
_audit_creation_method           
;
  Olex2 1.1
  (compiled 2011.02.15 svn.r1672, GUI svn.r3494)
;
_chemical_name_common            
'copper(II) complex of anthracene-9-imidazoline hydrazone'
_chemical_name_systematic        cis-[CuCl2(9-AIH)]
_chemical_formula_moiety         'C18 H16 Cl2 Cu N4, C2 H6 O'
_chemical_formula_sum            'C20 H18 Cl2 Cu N4 O'
_chemical_formula_weight         464.82
_chemical_melting_point          ?
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'

_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 1 21/c 1'
_space_group_name_Hall           '-P 2ybc'
loop_
_space_group_symop_id
_space_group_symop_operation_xyz
1 'x, y, z'
2 '-x, y+1/2, -z+1/2'
3 '-x, -y, -z'
4 'x, -y-1/2, z-1/2'

_cell_length_a                   11.3306(3)
_cell_length_b                   14.0417(3)
_cell_length_c                   13.3887(5)
_cell_angle_alpha                90.00
_cell_angle_beta                 106.842(4)
_cell_angle_gamma                90.00
_cell_volume                     2038.78(11)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    6202
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      28.6802
_cell_measurement_theta_min      2.8955
_exptl_absorpt_coefficient_mu    1.351
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.84408
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro, Agilent Technologies,
Version 1.171.35.19 (release 27-10-2011 CrysAlis171 .NET)
(compiled Oct 27 2011,15:02:11)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            red
_exptl_crystal_density_diffrn    1.514
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             948
_exptl_crystal_size_max          0.40
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.12
_exptl_special_details           
;
 ? 
;
_diffrn_reflns_av_R_equivalents  0.0301
_diffrn_reflns_av_unetI/netI     0.0270
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            16428
_diffrn_reflns_theta_full        26.37
_diffrn_reflns_theta_max         26.37
_diffrn_reflns_theta_min         2.90
_diffrn_ambient_temperature      293(2)
_diffrn_detector_area_resol_mean 16.1623
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_details      
;
#__ type_ start__ end____ width___ exp.time_
  1 omega  -79.00  -43.00   1.0000   20.2700
omega____ theta____ kappa____ phi______ frames
    -      -20.3518 -178.0000  -30.0000 36

#__ type_ start__ end____ width___ exp.time_
  2 omega  -12.00   16.00   1.0000   20.2700
omega____ theta____ kappa____ phi______ frames
    -       21.4455   80.0000   81.0000 28

#__ type_ start__ end____ width___ exp.time_
  3 omega   65.00  104.00   1.0000   20.2700
omega____ theta____ kappa____ phi______ frames
    -       21.4455 -178.0000 -150.0000 39

#__ type_ start__ end____ width___ exp.time_
  4 omega  -12.00   92.00   1.0000   20.2700
omega____ theta____ kappa____ phi______ frames
    -       21.4455   77.0000  -90.0000 104

#__ type_ start__ end____ width___ exp.time_
  5 omega    0.00   92.00   1.0000   20.2700
omega____ theta____ kappa____ phi______ frames
    -       21.4455   57.0000   30.0000 92

#__ type_ start__ end____ width___ exp.time_
  6 omega  -45.00  -16.00   1.0000   20.2700
omega____ theta____ kappa____ phi______ frames
    -       21.4455  -57.0000 -120.0000 29

#__ type_ start__ end____ width___ exp.time_
  7 omega  -50.00   39.00   1.0000   20.2700
omega____ theta____ kappa____ phi______ frames
    -       21.4455  -38.0000  120.0000 89

#__ type_ start__ end____ width___ exp.time_
  8 omega  -52.00    0.00   1.0000   20.2700
omega____ theta____ kappa____ phi______ frames
    -       21.4455  -38.0000  -90.0000 52
;
_diffrn_measurement_device_type  'SuperNova, Single source at offset), Eos'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_UB_11      -0.0020182000
_diffrn_orient_matrix_UB_12      -0.0395439000
_diffrn_orient_matrix_UB_13      -0.0334869000
_diffrn_orient_matrix_UB_21      0.0559124000
_diffrn_orient_matrix_UB_22      0.0152004000
_diffrn_orient_matrix_UB_23      -0.0086681000
_diffrn_orient_matrix_UB_31      0.0337559000
_diffrn_orient_matrix_UB_32      -0.0276228000
_diffrn_orient_matrix_UB_33      0.0431486000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.7107
_diffrn_source                   'SuperNova (Mo) X-ray Source'
_diffrn_standards_decay_%        ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_number         ?
_reflns_number_gt                3365
_reflns_number_total             4167
_reflns_odcompleteness_completeness 99.82
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     26.32
_reflns_threshold_expression     >2sigma(I)
_computing_cell_refinement       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.35.19 (release 27-10-2011 CrysAlis171 .NET)
(compiled Oct 27 2011,15:02:11)
;
_computing_data_collection       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.35.19 (release 27-10-2011 CrysAlis171 .NET)
(compiled Oct 27 2011,15:02:11)
;
_computing_data_reduction        
;
CrysAlisPro, Agilent Technologies,
Version 1.171.35.19 (release 27-10-2011 CrysAlis171 .NET)
(compiled Oct 27 2011,15:02:11)
;
_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_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    
'A short history of SHELX (Sheldrick, 2007)/Bruker'
_refine_diff_density_max         0.826
_refine_diff_density_min         -0.492
_refine_diff_density_rms         0.060
_refine_ls_extinction_coef       ?
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.034
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     268
_refine_ls_number_reflns         4167
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0563
_refine_ls_R_factor_gt           0.0444
_refine_ls_restrained_S_all      1.034
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0570P)²+2.0863P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1169
_refine_ls_wR_factor_ref         0.1257
_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. 
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
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 0.45358(4) 0.22778(3) 0.68935(3) 0.05097(16) Uani 1 1 d . . .
Cl1 Cl 0.31476(11) 0.29868(8) 0.55297(10) 0.0953(5) Uani 1 1 d . . .
Cl2 Cl 0.61290(8) 0.32462(6) 0.68392(8) 0.0577(2) Uani 1 1 d . . .
O O 0.3459(4) 0.2841(3) 0.8248(4) 0.1240(15) Uani 1 1 d . . .
HA H 0.3690 0.2619 0.8839 0.186 Uiso 0.643(9) 1 calc PR A 1
HB H 0.3544 0.2299 0.8485 0.186 Uiso 0.357(9) 1 calc PR A 2
N1 N 0.5556(2) 0.1521(2) 0.8019(2) 0.0514(7) Uani 1 1 d . . .
N2 N 0.5702(3) 0.0273(2) 0.9095(2) 0.0568(7) Uani 1 1 d . . .
H2 H 0.5456 -0.0217 0.9365 0.068 Uiso 1 1 calc R . .
N3 N 0.3900(2) 0.04955(18) 0.7689(2) 0.0484(7) Uani 1 1 d . . .
H3 H 0.3519 0.0010 0.7837 0.058 Uiso 1 1 calc R . .
N4 N 0.3400(2) 0.10872(17) 0.6851(2) 0.0417(6) Uani 1 1 d . . .
C1 C 0.6736(3) 0.1646(3) 0.8832(3) 0.0683(11) Uani 1 1 d . . .
H1A H 0.6705 0.2194 0.9266 0.082 Uiso 1 1 calc R . .
H1B H 0.7405 0.1732 0.8524 0.082 Uiso 1 1 calc R . .
C2 C 0.6903(3) 0.0726(3) 0.9469(3) 0.0649(10) Uani 1 1 d . . .
H2A H 0.7543 0.0331 0.9336 0.078 Uiso 1 1 calc R . .
H2B H 0.7109 0.0860 1.0210 0.078 Uiso 1 1 calc R . .
C3 C 0.5052(3) 0.0755(2) 0.8256(3) 0.0446(7) Uani 1 1 d . . .
C4 C 0.2363(3) 0.0870(2) 0.6211(2) 0.0421(7) Uani 1 1 d . . .
H4 H 0.2055 0.1286 0.5656 0.050 Uiso 1 1 calc R . .
C5 C 0.1595(2) 0.0025(2) 0.6257(2) 0.0368(6) Uani 1 1 d . . .
C6 C 0.0972(3) -0.0035(2) 0.7022(2) 0.0398(6) Uani 1 1 d . . .
C7 C 0.1094(3) 0.0662(2) 0.7819(3) 0.0516(8) Uani 1 1 d . . .
H7 H 0.1603 0.1187 0.7845 0.062 Uiso 1 1 calc R . .
C8 C 0.0471(4) 0.0564(3) 0.8541(3) 0.0645(10) Uani 1 1 d . . .
H8 H 0.0566 0.1021 0.9061 0.077 Uiso 1 1 calc R . .
C9 C -0.0318(4) -0.0220(3) 0.8517(3) 0.0675(11) Uani 1 1 d . . .
H9 H -0.0731 -0.0275 0.9021 0.081 Uiso 1 1 calc R . .
C10 C -0.0475(3) -0.0890(3) 0.7766(3) 0.0571(9) Uani 1 1 d . . .
H10 H -0.1006 -0.1398 0.7754 0.068 Uiso 1 1 calc R . .
C11 C 0.0161(3) -0.0830(2) 0.6989(2) 0.0428(7) Uani 1 1 d . . .
C12 C 0.0020(3) -0.1513(2) 0.6214(2) 0.0439(7) Uani 1 1 d . . .
H12 H -0.0515 -0.2019 0.6194 0.053 Uiso 1 1 calc R . .
C13 C 0.0651(3) -0.1466(2) 0.5466(2) 0.0391(6) Uani 1 1 d . . .
C14 C 0.0528(3) -0.2170(2) 0.4679(3) 0.0490(8) Uani 1 1 d . . .
H14 H -0.0008 -0.2678 0.4649 0.059 Uiso 1 1 calc R . .
C15 C 0.1174(3) -0.2118(2) 0.3973(3) 0.0553(9) Uani 1 1 d . . .
H15 H 0.1091 -0.2592 0.3473 0.066 Uiso 1 1 calc R . .
C16 C 0.1975(3) -0.1342(3) 0.4000(3) 0.0547(8) Uani 1 1 d . . .
H16 H 0.2416 -0.1307 0.3513 0.066 Uiso 1 1 calc R . .
C17 C 0.2106(3) -0.0650(2) 0.4723(3) 0.0470(7) Uani 1 1 d . . .
H17 H 0.2634 -0.0143 0.4723 0.056 Uiso 1 1 calc R . .
C18 C 0.1458(2) -0.06782(19) 0.5484(2) 0.0362(6) Uani 1 1 d . . .
C19 C 0.3568(9) 0.3863(7) 0.8300(8) 0.096(3) Uani 0.643(9) 1 d P A 1
H19A H 0.2906 0.4131 0.8535 0.115 Uiso 0.643(9) 1 calc PR A 1
H19B H 0.3505 0.4117 0.7613 0.115 Uiso 0.643(9) 1 calc PR A 1
C19' C 0.4173(16) 0.3545(12) 0.9091(14) 0.096(3) Uani 0.357(9) 1 d P A 2
H19C H 0.3757 0.3665 0.9618 0.115 Uiso 0.357(9) 1 calc PR A 2
H19D H 0.5014 0.3341 0.9420 0.115 Uiso 0.357(9) 1 calc PR A 2
C20 C 0.4762(9) 0.4124(8) 0.9029(9) 0.102(3) Uani 0.643(9) 1 d P A 1
H20A H 0.4840 0.3839 0.9697 0.153 Uiso 0.643(9) 1 calc PR A 1
H20B H 0.4813 0.4804 0.9102 0.153 Uiso 0.643(9) 1 calc PR A 1
H20C H 0.5415 0.3900 0.8765 0.153 Uiso 0.643(9) 1 calc PR A 1
C20' C 0.4108(19) 0.4389(15) 0.8374(14) 0.096(6) Uani 0.357(9) 1 d P A 2
H20D H 0.4617 0.4271 0.7926 0.144 Uiso 0.357(9) 1 calc PR A 2
H20E H 0.4394 0.4949 0.8784 0.144 Uiso 0.357(9) 1 calc PR A 2
H20F H 0.3270 0.4482 0.7958 0.144 Uiso 0.357(9) 1 calc PR A 2


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes) 
 are estimated using the full covariance matrix.  The cell esds are taken 
 into account individually in the estimation of esds in distances, angles 
 and torsion angles; correlations between esds in cell parameters are only 
 used when they are defined by crystal symmetry.  An approximate (isotropic) 
 treatment of cell esds is used for estimating esds involving l.s. planes. 
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Cu1 Cl1 2.2661(11) . ?
Cu1 Cl2 2.2780(9) . ?
Cu1 N1 1.931(3) . ?
Cu1 N4 2.100(2) . ?
O HA 0.8200 . ?
O HB 0.8200 . ?
O C19 1.440(10) . ?
O C19' 1.542(16) . ?
N1 C1 1.470(4) . ?
N1 C3 1.299(4) . ?
N2 H2 0.8600 . ?
N2 C2 1.454(5) . ?
N2 C3 1.336(4) . ?
N3 H3 0.8600 . ?
N3 N4 1.379(3) . ?
N3 C3 1.355(4) . ?
N4 C4 1.275(4) . ?
C1 H1A 0.9700 . ?
C1 H1B 0.9700 . ?
C1 C2 1.529(6) . ?
C2 H2A 0.9700 . ?
C2 H2B 0.9700 . ?
C4 H4 0.9300 . ?
C4 C5 1.483(4) . ?
C5 C6 1.405(4) . ?
C5 C18 1.407(4) . ?
C6 C7 1.424(4) . ?
C6 C11 1.439(4) . ?
C7 H7 0.9300 . ?
C7 C8 1.360(5) . ?
C8 H8 0.9300 . ?
C8 C9 1.412(6) . ?
C9 H9 0.9300 . ?
C9 C10 1.351(6) . ?
C10 H10 0.9300 . ?
C10 C11 1.430(5) . ?
C11 C12 1.388(5) . ?
C12 H12 0.9300 . ?
C12 C13 1.391(4) . ?
C13 C14 1.421(4) . ?
C13 C18 1.431(4) . ?
C14 H14 0.9300 . ?
C14 C15 1.355(5) . ?
C15 H15 0.9300 . ?
C15 C16 1.412(5) . ?
C16 H16 0.9300 . ?
C16 C17 1.349(5) . ?
C17 H17 0.9300 . ?
C17 C18 1.418(4) . ?
C19 H19A 0.9700 . ?
C19 H19B 0.9700 . ?
C19 C20 1.467(14) . ?
C19' H19C 0.9700 . ?
C19' H19D 0.9700 . ?
C19' C20' 1.51(3) . ?
C20 H20A 0.9600 . ?
C20 H20B 0.9600 . ?
C20 H20C 0.9600 . ?
C20' H20D 0.9600 . ?
C20' H20E 0.9600 . ?
C20' H20F 0.9600 . ?

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
Cl1 Cu1 Cl2 94.79(4) . . ?
N1 Cu1 Cl1 171.74(8) . . ?
N1 Cu1 Cl2 93.04(8) . . ?
N1 Cu1 N4 78.83(10) . . ?
N4 Cu1 Cl1 92.94(7) . . ?
N4 Cu1 Cl2 163.58(8) . . ?
HA O HB 45.8 . . ?
C19 O HA 109.5 . . ?
C19 O HB 155.1 . . ?
C19 O C19' 46.0(7) . . ?
C19' O HA 65.5 . . ?
C19' O HB 109.5 . . ?
C1 N1 Cu1 136.2(2) . . ?
C3 N1 Cu1 116.1(2) . . ?
C3 N1 C1 106.8(3) . . ?
C2 N2 H2 126.3 . . ?
C3 N2 H2 126.3 . . ?
C3 N2 C2 107.5(3) . . ?
N4 N3 H3 123.4 . . ?
C3 N3 H3 123.4 . . ?
C3 N3 N4 113.3(2) . . ?
N3 N4 Cu1 110.71(17) . . ?
C4 N4 Cu1 130.3(2) . . ?
C4 N4 N3 119.0(2) . . ?
N1 C1 H1A 110.8 . . ?
N1 C1 H1B 110.8 . . ?
N1 C1 C2 104.5(3) . . ?
H1A C1 H1B 108.9 . . ?
C2 C1 H1A 110.8 . . ?
C2 C1 H1B 110.8 . . ?
N2 C2 C1 103.1(3) . . ?
N2 C2 H2A 111.2 . . ?
N2 C2 H2B 111.2 . . ?
C1 C2 H2A 111.2 . . ?
C1 C2 H2B 111.2 . . ?
H2A C2 H2B 109.1 . . ?
N1 C3 N2 116.8(3) . . ?
N1 C3 N3 120.4(3) . . ?
N2 C3 N3 122.8(3) . . ?
N4 C4 H4 116.5 . . ?
N4 C4 C5 126.9(3) . . ?
C5 C4 H4 116.5 . . ?
C6 C5 C4 120.2(3) . . ?
C6 C5 C18 121.5(3) . . ?
C18 C5 C4 118.2(3) . . ?
C5 C6 C7 123.0(3) . . ?
C5 C6 C11 118.4(3) . . ?
C7 C6 C11 118.6(3) . . ?
C6 C7 H7 119.8 . . ?
C8 C7 C6 120.4(3) . . ?
C8 C7 H7 119.8 . . ?
C7 C8 H8 119.4 . . ?
C7 C8 C9 121.2(4) . . ?
C9 C8 H8 119.4 . . ?
C8 C9 H9 119.8 . . ?
C10 C9 C8 120.4(4) . . ?
C10 C9 H9 119.8 . . ?
C9 C10 H10 119.5 . . ?
C9 C10 C11 121.0(4) . . ?
C11 C10 H10 119.5 . . ?
C10 C11 C6 118.4(3) . . ?
C12 C11 C6 119.6(3) . . ?
C12 C11 C10 122.0(3) . . ?
C11 C12 H12 118.9 . . ?
C11 C12 C13 122.3(3) . . ?
C13 C12 H12 118.9 . . ?
C12 C13 C14 122.7(3) . . ?
C12 C13 C18 118.9(3) . . ?
C14 C13 C18 118.4(3) . . ?
C13 C14 H14 119.3 . . ?
C15 C14 C13 121.5(3) . . ?
C15 C14 H14 119.3 . . ?
C14 C15 H15 120.1 . . ?
C14 C15 C16 119.8(3) . . ?
C16 C15 H15 120.1 . . ?
C15 C16 H16 119.7 . . ?
C17 C16 C15 120.7(3) . . ?
C17 C16 H16 119.7 . . ?
C16 C17 H17 119.2 . . ?
C16 C17 C18 121.5(3) . . ?
C18 C17 H17 119.2 . . ?
C5 C18 C13 119.3(3) . . ?
C5 C18 C17 122.6(3) . . ?
C17 C18 C13 118.1(3) . . ?
O C19 H19A 109.8 . . ?
O C19 H19B 109.8 . . ?
O C19 C20 109.4(8) . . ?
H19A C19 H19B 108.2 . . ?
C20 C19 H19A 109.8 . . ?
C20 C19 H19B 109.8 . . ?
O C19' H19C 112.4 . . ?
O C19' H19D 112.4 . . ?
H19C C19' H19D 109.9 . . ?
C20' C19' O 96.8(13) . . ?
C20' C19' H19C 112.4 . . ?
C20' C19' H19D 112.4 . . ?
C19' C20' H20D 109.5 . . ?
C19' C20' H20E 109.5 . . ?
C19' C20' H20F 109.5 . . ?
H20D C20' H20E 109.5 . . ?
H20D C20' H20F 109.5 . . ?
H20E C20' H20F 109.5 . . ?

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
Cu1 N1 C1 C2 177.4(3) . . . . ?
Cu1 N1 C3 N2 -173.8(2) . . . . ?
Cu1 N1 C3 N3 3.6(4) . . . . ?
Cu1 N4 C4 C5 -177.8(2) . . . . ?
Cl1 Cu1 N1 C1 -177.9(6) . . . . ?
Cl1 Cu1 N1 C3 -10.3(9) . . . . ?
Cl1 Cu1 N4 N3 -173.3(2) . . . . ?
Cl1 Cu1 N4 C4 4.6(3) . . . . ?
Cl2 Cu1 N1 C1 20.8(4) . . . . ?
Cl2 Cu1 N1 C3 -171.6(3) . . . . ?
Cl2 Cu1 N4 N3 68.7(4) . . . . ?
Cl2 Cu1 N4 C4 -113.4(3) . . . . ?
N1 Cu1 N4 N3 7.3(2) . . . . ?
N1 Cu1 N4 C4 -174.8(3) . . . . ?
N1 C1 C2 N2 -11.5(4) . . . . ?
N3 N4 C4 C5 0.0(5) . . . . ?
N4 Cu1 N1 C1 -173.6(4) . . . . ?
N4 Cu1 N1 C3 -6.0(3) . . . . ?
N4 N3 C3 N1 3.1(5) . . . . ?
N4 N3 C3 N2 -179.6(3) . . . . ?
N4 C4 C5 C6 71.6(4) . . . . ?
N4 C4 C5 C18 -111.9(4) . . . . ?
C1 N1 C3 N2 -2.7(4) . . . . ?
C1 N1 C3 N3 174.7(3) . . . . ?
C2 N2 C3 N1 -5.3(4) . . . . ?
C2 N2 C3 N3 177.4(3) . . . . ?
C3 N1 C1 C2 9.0(4) . . . . ?
C3 N2 C2 C1 10.3(4) . . . . ?
C3 N3 N4 Cu1 -7.6(3) . . . . ?
C3 N3 N4 C4 174.3(3) . . . . ?
C4 C5 C6 C7 -3.9(4) . . . . ?
C4 C5 C6 C11 175.2(3) . . . . ?
C4 C5 C18 C13 -175.5(2) . . . . ?
C4 C5 C18 C17 5.6(4) . . . . ?
C5 C6 C7 C8 -179.7(3) . . . . ?
C5 C6 C11 C10 -179.8(3) . . . . ?
C5 C6 C11 C12 0.2(4) . . . . ?
C6 C5 C18 C13 1.0(4) . . . . ?
C6 C5 C18 C17 -178.0(3) . . . . ?
C6 C7 C8 C9 -0.6(5) . . . . ?
C6 C11 C12 C13 0.9(4) . . . . ?
C7 C6 C11 C10 -0.6(4) . . . . ?
C7 C6 C11 C12 179.4(3) . . . . ?
C7 C8 C9 C10 -0.4(6) . . . . ?
C8 C9 C10 C11 0.8(6) . . . . ?
C9 C10 C11 C6 -0.3(5) . . . . ?
C9 C10 C11 C12 179.6(3) . . . . ?
C10 C11 C12 C13 -179.0(3) . . . . ?
C11 C6 C7 C8 1.1(5) . . . . ?
C11 C12 C13 C14 179.0(3) . . . . ?
C11 C12 C13 C18 -1.1(4) . . . . ?
C12 C13 C14 C15 -178.6(3) . . . . ?
C12 C13 C18 C5 0.2(4) . . . . ?
C12 C13 C18 C17 179.2(3) . . . . ?
C13 C14 C15 C16 -1.2(5) . . . . ?
C14 C13 C18 C5 -179.9(3) . . . . ?
C14 C13 C18 C17 -0.9(4) . . . . ?
C14 C15 C16 C17 0.1(5) . . . . ?
C15 C16 C17 C18 0.4(5) . . . . ?
C16 C17 C18 C5 178.9(3) . . . . ?
C16 C17 C18 C13 0.0(4) . . . . ?
C18 C5 C6 C7 179.7(3) . . . . ?
C18 C5 C6 C11 -1.2(4) . . . . ?
C18 C13 C14 C15 1.5(5) . . . . ?
C19 O C19' C20' -18.2(9) . . . . ?
C19' O C19 C20 27.1(11) . . . . ?

_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: ethanol'
