# Electronic Supplementary Material (ESI) for Chemical Communications
# This journal is © The Royal Society of Chemistry 2013

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#                                CCDC 
# 
#######################################################################
# 
#  This CIF contains data from an original supplementary publication
#  deposited with the CCDC, and may include chemical, crystal,
#  experimental, refinement, atomic coordinates,
#  anisotropic displacement parameters and molecular geometry data,
#  as required by the journal to which it was submitted.
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#  fide research purposes only. It may contain copyright material
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data_ANDO967-sr

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
N-(9-Carboxamide)-N-(4-amino-2,2,6,6-tetramethylpiperidinooxy)-7,12-dihydroindolo-
[3,2-d][1]benzazepin-6(5H)-ylidene)-N'-(1-pyridin-2-yl-ethyliden]azin-5-ide-
chlorido-copper(II) tetrahydrofurane solvate 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         '2(C33 H35 Cl Cu N7 O2'
_chemical_formula_sum            'C66 H70 Cl2 Cu2 N14 O4'
_chemical_formula_weight         1321.34

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   P21/c
_symmetry_space_group_name_Hall  '-P 2ybc'

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                   12.7891(7)
_cell_length_b                   28.6933(15)
_cell_length_c                   11.9318(6)
_cell_angle_alpha                90.00
_cell_angle_beta                 104.934(3)
_cell_angle_gamma                90.00
_cell_volume                     4230.6(4)
_cell_formula_units_Z            2
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    6677
_cell_measurement_theta_min      2.69
_cell_measurement_theta_max      23.08

_exptl_crystal_description       plate
_exptl_crystal_colour            brown
_exptl_crystal_size_max          0.20
_exptl_crystal_size_mid          0.08
_exptl_crystal_size_min          0.02
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.037
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1376
_exptl_absorpt_coefficient_mu    0.611
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.8876
_exptl_absorpt_correction_T_max  0.9879
_exptl_absorpt_process_details   SADABS

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      100(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  'Bruker APEXII CCD'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            64583
_diffrn_reflns_av_R_equivalents  0.0895
_diffrn_reflns_av_sigmaI/netI    0.0613
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_k_min       -34
_diffrn_reflns_limit_k_max       34
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_theta_min         1.90
_diffrn_reflns_theta_max         25.00
_reflns_number_total             7437
_reflns_number_gt                5116
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'

_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. 
;

_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^)+(0.0899P)^2^+0.0000P] 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         7437
_refine_ls_number_parameters     398
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0856
_refine_ls_R_factor_gt           0.0554
_refine_ls_wR_factor_ref         0.1531
_refine_ls_wR_factor_gt          0.1434
_refine_ls_goodness_of_fit_ref   1.014
_refine_ls_restrained_S_all      1.014
_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 0.69381(3) 0.452678(16) 0.62769(3) 0.03126(16) Uani 1 1 d . . .
Cl1 Cl 0.80232(7) 0.51267(3) 0.70466(7) 0.0350(2) Uani 1 1 d . . .
N1 N 0.7875(2) 0.41777(10) 0.5493(2) 0.0319(7) Uani 1 1 d . . .
C2 C 0.9008(3) 0.41947(12) 0.5811(3) 0.0283(8) Uani 1 1 d . . .
C3 C 0.9520(3) 0.41426(13) 0.6993(3) 0.0361(9) Uani 1 1 d . . .
H3 H 0.9092 0.4084 0.7521 0.043 Uiso 1 1 calc R . .
C4 C 1.0616(3) 0.41742(15) 0.7407(3) 0.0449(10) Uani 1 1 d . . .
H4 H 1.0943 0.4127 0.8209 0.054 Uiso 1 1 calc R . .
C5 C 1.1250(3) 0.42758(15) 0.6657(3) 0.0471(10) Uani 1 1 d . . .
H5 H 1.2013 0.4299 0.6942 0.057 Uiso 1 1 calc R . .
C6 C 1.0767(3) 0.43436(14) 0.5490(3) 0.0412(9) Uani 1 1 d . . .
H6 H 1.1205 0.4421 0.4984 0.049 Uiso 1 1 calc R . .
C7 C 0.9649(3) 0.43005(13) 0.5038(3) 0.0312(8) Uani 1 1 d . . .
C8 C 0.9171(3) 0.43230(13) 0.3796(3) 0.0297(8) Uani 1 1 d . . .
N9 N 0.9540(2) 0.46039(11) 0.3043(2) 0.0365(8) Uani 1 1 d . . .
H9 H 1.0067 0.4809 0.3243 0.044 Uiso 1 1 calc R . .
C10 C 0.8955(3) 0.45133(13) 0.1935(3) 0.0340(8) Uani 1 1 d . . .
C11 C 0.9033(3) 0.46976(15) 0.0868(3) 0.0439(10) Uani 1 1 d . . .
H11 H 0.9517 0.4945 0.0834 0.053 Uiso 1 1 calc R . .
C12 C 0.8386(3) 0.45080(13) -0.0120(3) 0.0387(9) Uani 1 1 d . . .
H12 H 0.8423 0.4629 -0.0850 0.046 Uiso 1 1 calc R . .
C13 C 0.7674(3) 0.41432(13) -0.0092(3) 0.0366(9) Uani 1 1 d . . .
C14 C 0.7546(3) 0.39772(12) 0.0967(3) 0.0334(8) Uani 1 1 d . . .
H14 H 0.7026 0.3743 0.0988 0.040 Uiso 1 1 calc R . .
C15 C 0.8195(3) 0.41611(12) 0.1986(3) 0.0314(8) Uani 1 1 d . . .
C16 C 0.8345(3) 0.40535(12) 0.3182(3) 0.0293(8) Uani 1 1 d . . .
C17 C 0.7796(3) 0.36966(13) 0.3750(3) 0.0326(8) Uani 1 1 d . . .
H17A H 0.8329 0.3466 0.4173 0.039 Uiso 1 1 calc R . .
H17B H 0.7236 0.3529 0.3158 0.039 Uiso 1 1 calc R . .
C18 C 0.7284(3) 0.39495(12) 0.4579(3) 0.0297(8) Uani 1 1 d . . .
N19 N 0.6209(2) 0.39186(10) 0.4335(2) 0.0309(7) Uani 1 1 d . . .
N20 N 0.5861(2) 0.41933(10) 0.5095(2) 0.0309(7) Uani 1 1 d . . .
C21 C 0.4855(3) 0.42414(13) 0.5074(3) 0.0354(9) Uani 1 1 d . . .
C22 C 0.3960(3) 0.39777(14) 0.4259(4) 0.0521(11) Uani 1 1 d . . .
H22A H 0.4266 0.3778 0.3758 0.078 Uiso 1 1 calc R . .
H22B H 0.3451 0.4199 0.3780 0.078 Uiso 1 1 calc R . .
H22C H 0.3580 0.3785 0.4706 0.078 Uiso 1 1 calc R . .
C23 C 0.4666(3) 0.45717(12) 0.5919(3) 0.0333(8) Uani 1 1 d . . .
C24 C 0.3643(3) 0.47008(15) 0.6015(4) 0.0460(10) Uani 1 1 d . . .
H24 H 0.3013 0.4567 0.5518 0.055 Uiso 1 1 calc R . .
C25 C 0.3553(4) 0.50221(15) 0.6833(4) 0.0510(11) Uani 1 1 d . . .
H25 H 0.2860 0.5114 0.6904 0.061 Uiso 1 1 calc R . .
C26 C 0.4461(3) 0.52088(16) 0.7544(4) 0.0516(11) Uani 1 1 d . . .
H26 H 0.4409 0.5432 0.8115 0.062 Uiso 1 1 calc R . .
C27 C 0.5465(3) 0.50686(15) 0.7425(4) 0.0465(10) Uani 1 1 d . . .
H27 H 0.6101 0.5194 0.7930 0.056 Uiso 1 1 calc R . .
N28 N 0.5557(2) 0.47630(11) 0.6621(2) 0.0350(7) Uani 1 1 d . . .
O29 O 0.7216(2) 0.40646(9) -0.2131(2) 0.0443(7) Uani 1 1 d . . .
C30 C 0.7158(3) 0.39153(13) -0.1204(3) 0.0401(9) Uani 1 1 d . . .
N31 N 0.6683(3) 0.35033(14) -0.1182(3) 0.0687(12) Uani 1 1 d . . .
H31 H 0.6497 0.3417 -0.0552 0.082 Uiso 1 1 calc R . .
C32 C 0.6462(4) 0.31885(17) -0.2203(3) 0.0579(12) Uani 1 1 d . . .
H32 H 0.6208 0.3378 -0.2925 0.069 Uiso 1 1 calc R . .
C33 C 0.5628(4) 0.28562(16) -0.2135(4) 0.0589(12) Uani 1 1 d . . .
H33A H 0.4968 0.3028 -0.2092 0.071 Uiso 1 1 calc R . .
H33B H 0.5875 0.2671 -0.1415 0.071 Uiso 1 1 calc R . .
C34 C 0.5349(4) 0.25253(18) -0.3172(4) 0.0617(13) Uani 1 1 d . . .
N35 N 0.6358(3) 0.23350(12) -0.3421(3) 0.0553(10) Uani 1 1 d . . .
C36 C 0.7378(4) 0.26104(18) -0.3279(4) 0.0681(14) Uani 1 1 d . . .
C37 C 0.7496(4) 0.29352(17) -0.2243(4) 0.0677(14) Uani 1 1 d . . .
H37A H 0.7749 0.2751 -0.1522 0.081 Uiso 1 1 calc R . .
H37B H 0.8060 0.3170 -0.2259 0.081 Uiso 1 1 calc R . .
O38 O 0.6227(3) 0.20012(11) -0.4168(3) 0.0757(10) Uani 1 1 d . . .
C39 C 0.4702(5) 0.27653(19) -0.4255(4) 0.090(2) Uani 1 1 d . . .
H39A H 0.4039 0.2896 -0.4113 0.135 Uiso 1 1 calc R . .
H39B H 0.4512 0.2539 -0.4891 0.135 Uiso 1 1 calc R . .
H39C H 0.5134 0.3017 -0.4464 0.135 Uiso 1 1 calc R . .
C40 C 0.4762(5) 0.20951(18) -0.2862(5) 0.0806(16) Uani 1 1 d . . .
H40A H 0.4090 0.2193 -0.2680 0.121 Uiso 1 1 calc R . .
H40B H 0.5229 0.1939 -0.2186 0.121 Uiso 1 1 calc R . .
H40C H 0.4592 0.1880 -0.3521 0.121 Uiso 1 1 calc R . .
C41 C 0.7369(5) 0.28885(19) -0.4359(4) 0.0868(18) Uani 1 1 d . . .
H41A H 0.8051 0.3060 -0.4244 0.130 Uiso 1 1 calc R . .
H41B H 0.6764 0.3109 -0.4514 0.130 Uiso 1 1 calc R . .
H41C H 0.7286 0.2676 -0.5020 0.130 Uiso 1 1 calc R . .
C42 C 0.8341(4) 0.2264(2) -0.3087(6) 0.100(2) Uani 1 1 d . . .
H42A H 0.9017 0.2439 -0.2995 0.150 Uiso 1 1 calc R . .
H42B H 0.8237 0.2056 -0.3759 0.150 Uiso 1 1 calc R . .
H42C H 0.8377 0.2079 -0.2388 0.150 Uiso 1 1 calc R . .

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 0.0293(2) 0.0444(3) 0.0214(2) 0.00171(19) 0.00878(17) -0.0043(2)
Cl1 0.0324(5) 0.0435(6) 0.0294(5) 0.0015(4) 0.0083(4) -0.0064(4)
N1 0.0315(16) 0.0452(19) 0.0198(14) 0.0010(13) 0.0079(12) -0.0087(14)
C2 0.0272(18) 0.035(2) 0.0225(17) 0.0015(15) 0.0054(14) -0.0065(15)
C3 0.041(2) 0.045(2) 0.0242(18) 0.0029(16) 0.0109(16) -0.0038(18)
C4 0.036(2) 0.065(3) 0.031(2) 0.0095(19) 0.0039(17) -0.005(2)
C5 0.035(2) 0.067(3) 0.038(2) 0.007(2) 0.0056(17) -0.009(2)
C6 0.034(2) 0.060(3) 0.030(2) 0.0038(19) 0.0111(16) -0.0061(19)
C7 0.033(2) 0.038(2) 0.0236(18) 0.0031(15) 0.0096(15) -0.0072(16)
C8 0.0302(18) 0.039(2) 0.0227(17) 0.0020(16) 0.0117(14) -0.0030(16)
N9 0.0382(17) 0.049(2) 0.0248(15) 0.0028(14) 0.0127(13) -0.0171(15)
C10 0.039(2) 0.042(2) 0.0222(17) -0.0044(16) 0.0106(15) -0.0081(18)
C11 0.054(3) 0.051(2) 0.029(2) 0.0070(18) 0.0150(18) -0.014(2)
C12 0.050(2) 0.045(2) 0.0232(18) 0.0066(17) 0.0137(16) -0.0113(19)
C13 0.053(2) 0.038(2) 0.0198(18) 0.0017(16) 0.0114(16) -0.0074(18)
C14 0.047(2) 0.034(2) 0.0226(18) -0.0041(15) 0.0144(16) -0.0077(17)
C15 0.043(2) 0.033(2) 0.0228(18) -0.0006(15) 0.0162(15) -0.0063(16)
C16 0.039(2) 0.035(2) 0.0181(16) -0.0002(15) 0.0139(15) -0.0064(16)
C17 0.042(2) 0.037(2) 0.0219(17) -0.0031(15) 0.0145(15) -0.0109(17)
C18 0.037(2) 0.035(2) 0.0185(17) 0.0058(15) 0.0093(15) -0.0088(16)
N19 0.0340(17) 0.0369(18) 0.0202(14) 0.0025(13) 0.0039(12) -0.0076(14)
N20 0.0290(16) 0.0383(18) 0.0257(15) 0.0074(13) 0.0078(12) -0.0064(13)
C21 0.027(2) 0.037(2) 0.040(2) 0.0183(17) 0.0053(16) -0.0061(16)
C22 0.036(2) 0.040(2) 0.075(3) -0.001(2) 0.006(2) -0.0124(19)
C23 0.0287(19) 0.034(2) 0.040(2) 0.0167(17) 0.0130(16) -0.0025(17)
C24 0.032(2) 0.053(3) 0.056(3) 0.021(2) 0.0185(19) 0.0040(19)
C25 0.046(3) 0.048(3) 0.070(3) 0.023(2) 0.036(2) 0.010(2)
C26 0.056(3) 0.048(3) 0.060(3) 0.006(2) 0.031(2) 0.005(2)
C27 0.042(2) 0.057(3) 0.048(2) 0.001(2) 0.0245(19) -0.003(2)
N28 0.0358(17) 0.0374(18) 0.0355(17) 0.0073(15) 0.0159(14) -0.0003(14)
O29 0.0616(18) 0.0500(17) 0.0209(13) 0.0093(12) 0.0100(12) -0.0043(14)
C30 0.060(3) 0.040(2) 0.0229(19) 0.0004(17) 0.0150(17) -0.011(2)
N31 0.111(3) 0.068(3) 0.0289(19) -0.0096(18) 0.021(2) -0.036(2)
C32 0.086(4) 0.058(3) 0.031(2) 0.002(2) 0.017(2) 0.001(3)
C33 0.071(3) 0.058(3) 0.045(3) -0.011(2) 0.009(2) 0.000(2)
C34 0.071(3) 0.069(3) 0.039(2) -0.009(2) 0.003(2) -0.005(3)
N35 0.081(3) 0.043(2) 0.039(2) -0.0063(17) 0.0114(19) 0.013(2)
C36 0.092(4) 0.064(3) 0.054(3) 0.011(3) 0.030(3) -0.004(3)
C37 0.101(4) 0.062(3) 0.042(3) 0.005(2) 0.022(3) -0.013(3)
O38 0.118(3) 0.048(2) 0.060(2) -0.0041(17) 0.022(2) 0.0168(19)
C39 0.112(5) 0.069(4) 0.066(3) -0.017(3) -0.016(3) 0.037(3)
C40 0.095(4) 0.069(4) 0.074(4) -0.017(3) 0.015(3) -0.007(3)
C41 0.147(6) 0.065(4) 0.058(3) -0.002(3) 0.045(3) -0.010(4)
C42 0.078(4) 0.077(4) 0.162(6) 0.030(4) 0.061(4) 0.014(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 N20 1.950(3) . ?
Cu1 N1 1.973(3) . ?
Cu1 N28 2.029(3) . ?
Cu1 Cl1 2.2529(10) . ?
Cu1 O29 2.269(2) 1_556 ?
N1 C18 1.329(4) . ?
N1 C2 1.400(4) . ?
C2 C3 1.402(4) . ?
C2 C7 1.416(5) . ?
C3 C4 1.363(5) . ?
C3 H3 0.9500 . ?
C4 C5 1.385(5) . ?
C4 H4 0.9500 . ?
C5 C6 1.384(5) . ?
C5 H5 0.9500 . ?
C6 C7 1.397(5) . ?
C6 H6 0.9500 . ?
C7 C8 1.451(4) . ?
C8 C16 1.362(5) . ?
C8 N9 1.378(4) . ?
N9 C10 1.366(4) . ?
N9 H9 0.8800 . ?
C10 C11 1.405(5) . ?
C10 C15 1.415(5) . ?
C11 C12 1.366(5) . ?
C11 H11 0.9500 . ?
C12 C13 1.393(5) . ?
C12 H12 0.9500 . ?
C13 C14 1.399(5) . ?
C13 C30 1.474(5) . ?
C14 C15 1.388(5) . ?
C14 H14 0.9500 . ?
C15 C16 1.424(4) . ?
C16 C17 1.499(5) . ?
C17 C18 1.506(5) . ?
C17 H17A 0.9900 . ?
C17 H17B 0.9900 . ?
C18 N19 1.333(4) . ?
N19 N20 1.361(4) . ?
N20 C21 1.288(4) . ?
C21 C23 1.448(5) . ?
C21 C22 1.502(5) . ?
C22 H22A 0.9800 . ?
C22 H22B 0.9800 . ?
C22 H22C 0.9800 . ?
C23 N28 1.345(4) . ?
C23 C24 1.393(5) . ?
C24 C25 1.369(6) . ?
C24 H24 0.9500 . ?
C25 C26 1.359(6) . ?
C25 H25 0.9500 . ?
C26 C27 1.387(5) . ?
C26 H26 0.9500 . ?
C27 N28 1.327(5) . ?
C27 H27 0.9500 . ?
O29 C30 1.206(4) . ?
O29 Cu1 2.269(2) 1_554 ?
C30 N31 1.333(5) . ?
N31 C32 1.484(5) . ?
N31 H31 0.8800 . ?
C32 C33 1.448(6) . ?
C32 C37 1.520(7) . ?
C32 H32 1.0000 . ?
C33 C34 1.526(6) . ?
C33 H33A 0.9900 . ?
C33 H33B 0.9900 . ?
C34 N35 1.500(6) . ?
C34 C39 1.509(6) . ?
C34 C40 1.539(7) . ?
N35 O38 1.290(4) . ?
N35 C36 1.497(6) . ?
C36 C41 1.514(6) . ?
C36 C37 1.524(6) . ?
C36 C42 1.552(7) . ?
C37 H37A 0.9900 . ?
C37 H37B 0.9900 . ?
C39 H39A 0.9800 . ?
C39 H39B 0.9800 . ?
C39 H39C 0.9800 . ?
C40 H40A 0.9800 . ?
C40 H40B 0.9800 . ?
C40 H40C 0.9800 . ?
C41 H41A 0.9800 . ?
C41 H41B 0.9800 . ?
C41 H41C 0.9800 . ?
C42 H42A 0.9800 . ?
C42 H42B 0.9800 . ?
C42 H42C 0.9800 . ?

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
N20 Cu1 N1 79.07(12) . . ?
N20 Cu1 N28 79.65(12) . . ?
N1 Cu1 N28 158.72(12) . . ?
N20 Cu1 Cl1 156.37(9) . . ?
N1 Cu1 Cl1 101.28(9) . . ?
N28 Cu1 Cl1 97.99(9) . . ?
N20 Cu1 O29 104.34(11) . 1_556 ?
N1 Cu1 O29 96.73(11) . 1_556 ?
N28 Cu1 O29 89.00(11) . 1_556 ?
Cl1 Cu1 O29 99.10(7) . 1_556 ?
C18 N1 C2 124.8(3) . . ?
C18 N1 Cu1 110.6(2) . . ?
C2 N1 Cu1 124.5(2) . . ?
N1 C2 C3 116.9(3) . . ?
N1 C2 C7 124.2(3) . . ?
C3 C2 C7 118.6(3) . . ?
C4 C3 C2 121.9(3) . . ?
C4 C3 H3 119.1 . . ?
C2 C3 H3 119.1 . . ?
C3 C4 C5 119.9(4) . . ?
C3 C4 H4 120.1 . . ?
C5 C4 H4 120.1 . . ?
C6 C5 C4 119.7(4) . . ?
C6 C5 H5 120.1 . . ?
C4 C5 H5 120.1 . . ?
C5 C6 C7 121.5(3) . . ?
C5 C6 H6 119.2 . . ?
C7 C6 H6 119.2 . . ?
C6 C7 C2 118.3(3) . . ?
C6 C7 C8 120.6(3) . . ?
C2 C7 C8 120.8(3) . . ?
C16 C8 N9 109.2(3) . . ?
C16 C8 C7 126.1(3) . . ?
N9 C8 C7 124.6(3) . . ?
C10 N9 C8 109.1(3) . . ?
C10 N9 H9 125.5 . . ?
C8 N9 H9 125.5 . . ?
N9 C10 C11 131.0(3) . . ?
N9 C10 C15 107.7(3) . . ?
C11 C10 C15 121.2(3) . . ?
C12 C11 C10 117.6(4) . . ?
C12 C11 H11 121.2 . . ?
C10 C11 H11 121.2 . . ?
C11 C12 C13 122.2(3) . . ?
C11 C12 H12 118.9 . . ?
C13 C12 H12 118.9 . . ?
C12 C13 C14 120.4(3) . . ?
C12 C13 C30 117.1(3) . . ?
C14 C13 C30 122.2(3) . . ?
C15 C14 C13 118.7(3) . . ?
C15 C14 H14 120.7 . . ?
C13 C14 H14 120.7 . . ?
C14 C15 C10 119.7(3) . . ?
C14 C15 C16 133.8(3) . . ?
C10 C15 C16 106.4(3) . . ?
C8 C16 C15 107.6(3) . . ?
C8 C16 C17 122.3(3) . . ?
C15 C16 C17 130.0(3) . . ?
C16 C17 C18 107.6(3) . . ?
C16 C17 H17A 110.2 . . ?
C18 C17 H17A 110.2 . . ?
C16 C17 H17B 110.2 . . ?
C18 C17 H17B 110.2 . . ?
H17A C17 H17B 108.5 . . ?
N1 C18 N19 123.3(3) . . ?
N1 C18 C17 121.6(3) . . ?
N19 C18 C17 115.0(3) . . ?
C18 N19 N20 108.2(3) . . ?
C21 N20 N19 123.1(3) . . ?
C21 N20 Cu1 118.5(3) . . ?
N19 N20 Cu1 118.3(2) . . ?
N20 C21 C23 113.7(3) . . ?
N20 C21 C22 123.3(4) . . ?
C23 C21 C22 123.0(3) . . ?
C21 C22 H22A 109.5 . . ?
C21 C22 H22B 109.5 . . ?
H22A C22 H22B 109.5 . . ?
C21 C22 H22C 109.5 . . ?
H22A C22 H22C 109.5 . . ?
H22B C22 H22C 109.5 . . ?
N28 C23 C24 120.2(4) . . ?
N28 C23 C21 115.7(3) . . ?
C24 C23 C21 124.1(4) . . ?
C25 C24 C23 119.4(4) . . ?
C25 C24 H24 120.3 . . ?
C23 C24 H24 120.3 . . ?
C26 C25 C24 119.7(4) . . ?
C26 C25 H25 120.2 . . ?
C24 C25 H25 120.2 . . ?
C25 C26 C27 119.1(4) . . ?
C25 C26 H26 120.5 . . ?
C27 C26 H26 120.5 . . ?
N28 C27 C26 121.5(4) . . ?
N28 C27 H27 119.2 . . ?
C26 C27 H27 119.2 . . ?
C27 N28 C23 120.1(3) . . ?
C27 N28 Cu1 127.6(3) . . ?
C23 N28 Cu1 112.3(2) . . ?
C30 O29 Cu1 160.4(3) . 1_554 ?
O29 C30 N31 118.0(3) . . ?
O29 C30 C13 123.3(3) . . ?
N31 C30 C13 118.4(3) . . ?
C30 N31 C32 121.0(3) . . ?
C30 N31 H31 119.5 . . ?
C32 N31 H31 119.5 . . ?
C33 C32 N31 110.0(4) . . ?
C33 C32 C37 110.2(4) . . ?
N31 C32 C37 109.5(4) . . ?
C33 C32 H32 109.0 . . ?
N31 C32 H32 109.0 . . ?
C37 C32 H32 109.0 . . ?
C32 C33 C34 112.7(4) . . ?
C32 C33 H33A 109.0 . . ?
C34 C33 H33A 109.0 . . ?
C32 C33 H33B 109.0 . . ?
C34 C33 H33B 109.0 . . ?
H33A C33 H33B 107.8 . . ?
N35 C34 C39 107.8(4) . . ?
N35 C34 C33 110.7(4) . . ?
C39 C34 C33 111.8(4) . . ?
N35 C34 C40 104.7(4) . . ?
C39 C34 C40 112.2(4) . . ?
C33 C34 C40 109.3(4) . . ?
O38 N35 C36 115.1(4) . . ?
O38 N35 C34 116.3(4) . . ?
C36 N35 C34 123.7(4) . . ?
N35 C36 C41 111.5(4) . . ?
N35 C36 C37 108.4(4) . . ?
C41 C36 C37 110.2(4) . . ?
N35 C36 C42 108.3(4) . . ?
C41 C36 C42 107.1(4) . . ?
C37 C36 C42 111.3(5) . . ?
C32 C37 C36 114.4(4) . . ?
C32 C37 H37A 108.7 . . ?
C36 C37 H37A 108.7 . . ?
C32 C37 H37B 108.7 . . ?
C36 C37 H37B 108.7 . . ?
H37A C37 H37B 107.6 . . ?
C34 C39 H39A 109.5 . . ?
C34 C39 H39B 109.5 . . ?
H39A C39 H39B 109.5 . . ?
C34 C39 H39C 109.5 . . ?
H39A C39 H39C 109.5 . . ?
H39B C39 H39C 109.5 . . ?
C34 C40 H40A 109.5 . . ?
C34 C40 H40B 109.5 . . ?
H40A C40 H40B 109.5 . . ?
C34 C40 H40C 109.5 . . ?
H40A C40 H40C 109.5 . . ?
H40B C40 H40C 109.5 . . ?
C36 C41 H41A 109.5 . . ?
C36 C41 H41B 109.5 . . ?
H41A C41 H41B 109.5 . . ?
C36 C41 H41C 109.5 . . ?
H41A C41 H41C 109.5 . . ?
H41B C41 H41C 109.5 . . ?
C36 C42 H42A 109.5 . . ?
C36 C42 H42B 109.5 . . ?
H42A C42 H42B 109.5 . . ?
C36 C42 H42C 109.5 . . ?
H42A C42 H42C 109.5 . . ?
H42B C42 H42C 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
N20 Cu1 N1 C18 4.9(2) . . . . ?
N28 Cu1 N1 C18 3.5(5) . . . . ?
Cl1 Cu1 N1 C18 -151.0(2) . . . . ?
O29 Cu1 N1 C18 108.3(2) 1_556 . . . ?
N20 Cu1 N1 C2 -179.2(3) . . . . ?
N28 Cu1 N1 C2 179.5(3) . . . . ?
Cl1 Cu1 N1 C2 24.9(3) . . . . ?
O29 Cu1 N1 C2 -75.8(3) 1_556 . . . ?
C18 N1 C2 C3 -136.9(4) . . . . ?
Cu1 N1 C2 C3 47.7(4) . . . . ?
C18 N1 C2 C7 48.8(5) . . . . ?
Cu1 N1 C2 C7 -126.6(3) . . . . ?
N1 C2 C3 C4 -177.0(3) . . . . ?
C7 C2 C3 C4 -2.4(6) . . . . ?
C2 C3 C4 C5 2.2(6) . . . . ?
C3 C4 C5 C6 -0.2(7) . . . . ?
C4 C5 C6 C7 -1.6(7) . . . . ?
C5 C6 C7 C2 1.4(6) . . . . ?
C5 C6 C7 C8 -173.3(4) . . . . ?
N1 C2 C7 C6 174.8(3) . . . . ?
C3 C2 C7 C6 0.6(5) . . . . ?
N1 C2 C7 C8 -10.6(6) . . . . ?
C3 C2 C7 C8 175.3(3) . . . . ?
C6 C7 C8 C16 140.0(4) . . . . ?
C2 C7 C8 C16 -34.5(6) . . . . ?
C6 C7 C8 N9 -35.5(6) . . . . ?
C2 C7 C8 N9 150.0(4) . . . . ?
C16 C8 N9 C10 -0.5(4) . . . . ?
C7 C8 N9 C10 175.7(3) . . . . ?
C8 N9 C10 C11 -178.4(4) . . . . ?
C8 N9 C10 C15 -0.4(4) . . . . ?
N9 C10 C11 C12 174.6(4) . . . . ?
C15 C10 C11 C12 -3.2(6) . . . . ?
C10 C11 C12 C13 -0.4(6) . . . . ?
C11 C12 C13 C14 4.2(6) . . . . ?
C11 C12 C13 C30 -169.8(4) . . . . ?
C12 C13 C14 C15 -4.3(6) . . . . ?
C30 C13 C14 C15 169.4(4) . . . . ?
C13 C14 C15 C10 0.7(5) . . . . ?
C13 C14 C15 C16 -174.2(4) . . . . ?
N9 C10 C15 C14 -175.2(3) . . . . ?
C11 C10 C15 C14 3.1(6) . . . . ?
N9 C10 C15 C16 1.0(4) . . . . ?
C11 C10 C15 C16 179.3(4) . . . . ?
N9 C8 C16 C15 1.1(4) . . . . ?
C7 C8 C16 C15 -175.0(3) . . . . ?
N9 C8 C16 C17 177.7(3) . . . . ?
C7 C8 C16 C17 1.6(6) . . . . ?
C14 C15 C16 C8 174.1(4) . . . . ?
C10 C15 C16 C8 -1.3(4) . . . . ?
C14 C15 C16 C17 -2.1(7) . . . . ?
C10 C15 C16 C17 -177.5(4) . . . . ?
C8 C16 C17 C18 61.9(4) . . . . ?
C15 C16 C17 C18 -122.3(4) . . . . ?
C2 N1 C18 N19 176.2(3) . . . . ?
Cu1 N1 C18 N19 -7.9(4) . . . . ?
C2 N1 C18 C17 -2.6(5) . . . . ?
Cu1 N1 C18 C17 173.3(2) . . . . ?
C16 C17 C18 N1 -63.9(4) . . . . ?
C16 C17 C18 N19 117.3(3) . . . . ?
N1 C18 N19 N20 6.1(4) . . . . ?
C17 C18 N19 N20 -175.1(3) . . . . ?
C18 N19 N20 C21 179.2(3) . . . . ?
C18 N19 N20 Cu1 -1.1(3) . . . . ?
N1 Cu1 N20 C21 177.5(3) . . . . ?
N28 Cu1 N20 C21 -3.0(3) . . . . ?
Cl1 Cu1 N20 C21 -89.3(3) . . . . ?
O29 Cu1 N20 C21 83.3(3) 1_556 . . . ?
N1 Cu1 N20 N19 -2.2(2) . . . . ?
N28 Cu1 N20 N19 177.3(2) . . . . ?
Cl1 Cu1 N20 N19 91.0(3) . . . . ?
O29 Cu1 N20 N19 -96.4(2) 1_556 . . . ?
N19 N20 C21 C23 -176.5(3) . . . . ?
Cu1 N20 C21 C23 3.8(4) . . . . ?
N19 N20 C21 C22 3.9(5) . . . . ?
Cu1 N20 C21 C22 -175.7(3) . . . . ?
N20 C21 C23 N28 -2.5(4) . . . . ?
C22 C21 C23 N28 177.1(3) . . . . ?
N20 C21 C23 C24 176.3(3) . . . . ?
C22 C21 C23 C24 -4.2(5) . . . . ?
N28 C23 C24 C25 -0.3(5) . . . . ?
C21 C23 C24 C25 -179.0(3) . . . . ?
C23 C24 C25 C26 -0.4(6) . . . . ?
C24 C25 C26 C27 0.0(6) . . . . ?
C25 C26 C27 N28 1.1(6) . . . . ?
C26 C27 N28 C23 -1.8(6) . . . . ?
C26 C27 N28 Cu1 178.3(3) . . . . ?
C24 C23 N28 C27 1.4(5) . . . . ?
C21 C23 N28 C27 -179.8(3) . . . . ?
C24 C23 N28 Cu1 -178.7(3) . . . . ?
C21 C23 N28 Cu1 0.1(4) . . . . ?
N20 Cu1 N28 C27 -178.7(3) . . . . ?
N1 Cu1 N28 C27 -177.3(3) . . . . ?
Cl1 Cu1 N28 C27 -22.5(3) . . . . ?
O29 Cu1 N28 C27 76.5(3) 1_556 . . . ?
N20 Cu1 N28 C23 1.4(2) . . . . ?
N1 Cu1 N28 C23 2.8(5) . . . . ?
Cl1 Cu1 N28 C23 157.6(2) . . . . ?
O29 Cu1 N28 C23 -103.4(2) 1_556 . . . ?
Cu1 O29 C30 N31 113.8(7) 1_554 . . . ?
Cu1 O29 C30 C13 -72.2(9) 1_554 . . . ?
C12 C13 C30 O29 -9.6(6) . . . . ?
C14 C13 C30 O29 176.5(4) . . . . ?
C12 C13 C30 N31 164.4(4) . . . . ?
C14 C13 C30 N31 -9.5(6) . . . . ?
O29 C30 N31 C32 13.9(7) . . . . ?
C13 C30 N31 C32 -160.4(4) . . . . ?
C30 N31 C32 C33 -159.6(4) . . . . ?
C30 N31 C32 C37 79.1(5) . . . . ?
N31 C32 C33 C34 179.1(4) . . . . ?
C37 C32 C33 C34 -60.0(5) . . . . ?
C32 C33 C34 N35 46.7(5) . . . . ?
C32 C33 C34 C39 -73.5(6) . . . . ?
C32 C33 C34 C40 161.6(4) . . . . ?
C39 C34 N35 O38 -67.0(5) . . . . ?
C33 C34 N35 O38 170.4(4) . . . . ?
C40 C34 N35 O38 52.7(4) . . . . ?
C39 C34 N35 C36 86.8(5) . . . . ?
C33 C34 N35 C36 -35.8(5) . . . . ?
C40 C34 N35 C36 -153.5(4) . . . . ?
O38 N35 C36 C41 67.4(5) . . . . ?
C34 N35 C36 C41 -86.7(5) . . . . ?
O38 N35 C36 C37 -171.1(4) . . . . ?
C34 N35 C36 C37 34.8(5) . . . . ?
O38 N35 C36 C42 -50.2(5) . . . . ?
C34 N35 C36 C42 155.7(4) . . . . ?
C33 C32 C37 C36 60.5(5) . . . . ?
N31 C32 C37 C36 -178.3(4) . . . . ?
N35 C36 C37 C32 -44.7(5) . . . . ?
C41 C36 C37 C32 77.6(6) . . . . ?
C42 C36 C37 C32 -163.7(4) . . . . ?

_diffrn_measured_fraction_theta_max 0.998
_diffrn_reflns_theta_full        25.00
_diffrn_measured_fraction_theta_full 0.998
_refine_diff_density_max         0.687
_refine_diff_density_min         -0.385
_refine_diff_density_rms         0.069
_database_code_depnum_ccdc_archive 'CCDC 952588'