# Electronic Supplementary Material (ESI) for Dalton Transactions.
# This journal is © The Royal Society of Chemistry 2014

#######################################################################
#
#                 Cambridge Crystallographic Data Centre
#                                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.
#
#  This CIF is provided on the understanding that it is used for bona
#  fide research purposes only. It may contain copyright material
#  of the CCDC or of third parties, and may not be copied or further
#  disseminated in any form, whether machine-readable or not,
#  except for the purpose of generating routine backup copies
#  on your local computer system.
# 
#  For further information on the CCDC, data deposition and
#  data retrieval see:
#                         www.ccdc.cam.ac.uk
#
#  Bona fide researchers may freely download Mercury and enCIFer
#  from this site to visualise CIF-encoded structures and 
#  to carry out CIF format checking respectively.
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data_mb33-r-3i

_audit_creation_method           SHELXL-97
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_formula_moiety         '(Cu 2+) (Cl -1) (C22 H27 N2 O -1)0.0417(H2O)'
_chemical_formula_sum            'C22 H29.08 Cl Cu N2 O1.04'
_chemical_melting_point          ?

_exptl_crystal_description       ?
_exptl_crystal_colour            ?

_diffrn_ambient_temperature      293(2)
_chemical_formula_weight         437.21

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           rhombohedral
_symmetry_space_group_name_H-M   'R -3'
_symmetry_int_tables_number      148
_chemical_absolute_configuration ?

loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'z, x, y'
'y, z, x'
'-x, -y, -z'
'-z, -x, -y'
'-y, -z, -x'

_cell_length_a                   15.8718(2)
_cell_length_b                   15.8718(2)
_cell_length_c                   15.8718(2)
_cell_angle_alpha                106.6390(10)
_cell_angle_beta                 106.6390(10)
_cell_angle_gamma                106.6390(10)
_cell_volume                     3362.10(7)
_cell_formula_units_Z            6
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    ?
_cell_measurement_theta_min      ?
_cell_measurement_theta_max      ?
_exptl_crystal_size_max          0.63
_exptl_crystal_size_mid          0.49
_exptl_crystal_size_min          0.18
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.296
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1377
_exptl_absorpt_coefficient_mu    1.107
_exptl_absorpt_correction_type   numerical
_exptl_absorpt_correction_T_min  0.5423
_exptl_absorpt_correction_T_max  0.8256
_exptl_absorpt_process_details   'CrysAlis CCD, Oxford 2001'

_exptl_special_details           
;
  ?
;
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Oxford Sapphire CCD diffractometer'
_diffrn_measurement_method       ?
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            22072
_diffrn_reflns_av_R_equivalents  0.0844
_diffrn_reflns_av_sigmaI/netI    0.0538
_diffrn_reflns_limit_h_min       -20
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       -20
_diffrn_reflns_limit_k_max       20
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_theta_min         2.45
_diffrn_reflns_theta_max         27.09
_reflns_number_total             4873
_reflns_number_gt                3560
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'CrysAlis CCD'
_computing_cell_refinement       ?
_computing_data_reduction        'CrysAlis RED 171'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    ?
_computing_publication_material  CIFTAB

_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)+(0.0658P)²+0.0000P] 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         4873
_refine_ls_number_parameters     252
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0548
_refine_ls_R_factor_gt           0.0381
_refine_ls_wR_factor_ref         0.1103
_refine_ls_wR_factor_gt          0.1060
_refine_ls_goodness_of_fit_ref   1.000
_refine_ls_restrained_S_all      1.000
_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 0.021750(19) 0.943920(19) 0.343948(19) 0.03779(12) Uani 1 1 d . . .
Cl2 Cl 0.12179(5) 0.87104(5) 0.36189(5) 0.05192(18) Uani 1 1 d . . .
O1 O 0.12017(11) 1.06728(11) 0.40930(12) 0.0452(4) Uani 1 1 d . . .
C2 C 0.11867(15) 1.14791(16) 0.45732(15) 0.0345(5) Uani 1 1 d . . .
C3 C 0.20220(16) 1.23474(16) 0.49720(15) 0.0370(5) Uani 1 1 d . . .
C4 C 0.19775(17) 1.31735(17) 0.54799(17) 0.0433(6) Uani 1 1 d . . .
H4 H 0.2522 1.3739 0.5733 0.052 Uiso 1 1 calc R . .
C5 C 0.11717(18) 1.32381(17) 0.56516(17) 0.0438(6) Uani 1 1 d . A .
C6 C 0.03803(17) 1.24087(17) 0.52592(16) 0.0417(5) Uani 1 1 d . . .
H6 H -0.0169 1.2425 0.5351 0.050 Uiso 1 1 calc R . .
C7 C 0.03586(15) 1.15270(16) 0.47191(15) 0.0361(5) Uani 1 1 d . . .
C8 C -0.05314(16) 1.07084(17) 0.43109(16) 0.0382(5) Uani 1 1 d . . .
H8 H -0.1029 1.0817 0.4455 0.046 Uiso 1 1 calc R . .
N9 N -0.07282(12) 0.98434(13) 0.37703(12) 0.0362(4) Uani 1 1 d . . .
C10 C -0.17291(16) 0.91700(18) 0.33959(18) 0.0466(6) Uani 1 1 d . . .
H10A H -0.2129 0.9352 0.2956 0.056 Uiso 1 1 calc R . .
H10B H -0.1930 0.9218 0.3924 0.056 Uiso 1 1 calc R . .
C11 C -0.1889(2) 0.81324(19) 0.28776(19) 0.0546(7) Uani 1 1 d . . .
H11A H -0.1496 0.7949 0.3322 0.065 Uiso 1 1 calc R . .
H11B H -0.2556 0.7723 0.2684 0.065 Uiso 1 1 calc R . .
C12 C -0.16583(19) 0.79601(17) 0.20168(18) 0.0480(6) Uani 1 1 d . . .
C13 C -0.2333(2) 0.7323(2) 0.1096(2) 0.0663(8) Uani 1 1 d . . .
H13 H -0.2962 0.6987 0.0996 0.080 Uiso 1 1 calc R . .
C14 C -0.2063(3) 0.7195(2) 0.0338(2) 0.0769(11) Uani 1 1 d . . .
H14 H -0.2510 0.6774 -0.0279 0.092 Uiso 1 1 calc R . .
C15 C -0.1141(3) 0.7683(2) 0.0491(2) 0.0727(9) Uani 1 1 d . . .
H15 H -0.0951 0.7601 -0.0019 0.087 Uiso 1 1 calc R . .
C16 C -0.0491(2) 0.8303(2) 0.14114(19) 0.0593(7) Uani 1 1 d . . .
H16 H 0.0142 0.8635 0.1517 0.071 Uiso 1 1 calc R . .
N17 N -0.07468(16) 0.84420(14) 0.21627(14) 0.0464(5) Uani 1 1 d . . .
C31 C 0.29341(17) 1.23254(17) 0.48302(18) 0.0439(6) Uani 1 1 d . . .
C32 C 0.32974(19) 1.1708(2) 0.5283(2) 0.0625(8) Uani 1 1 d . . .
H32A H 0.3895 1.1742 0.5237 0.094 Uiso 1 1 calc R . .
H32B H 0.2835 1.1055 0.4953 0.094 Uiso 1 1 calc R . .
H32C H 0.3392 1.1938 0.5946 0.094 Uiso 1 1 calc R . .
C33 C 0.3736(2) 1.3325(2) 0.5289(2) 0.0710(9) Uani 1 1 d . . .
H33A H 0.4307 1.3279 0.5227 0.107 Uiso 1 1 calc R . .
H33B H 0.3860 1.3613 0.5956 0.107 Uiso 1 1 calc R . .
H33C H 0.3545 1.3714 0.4972 0.107 Uiso 1 1 calc R . .
C34 C 0.2719(2) 1.1919(2) 0.3757(2) 0.0638(8) Uani 1 1 d . . .
H34A H 0.2459 1.2290 0.3463 0.096 Uiso 1 1 calc R . .
H34B H 0.2262 1.1263 0.3461 0.096 Uiso 1 1 calc R . .
H34C H 0.3301 1.1947 0.3674 0.096 Uiso 1 1 calc R . .
C51 C 0.1229(2) 1.41971(19) 0.6291(2) 0.0621(8) Uani 1 1 d . . .
C52 C 0.2003(3) 1.4540(3) 0.7301(3) 0.1188(17) Uani 1 1 d . A 1
H52A H 0.2089 1.5171 0.7689 0.178 Uiso 1 1 calc R A 1
H52B H 0.2598 1.4558 0.7256 0.178 Uiso 1 1 calc R A 1
H52C H 0.1806 1.4106 0.7589 0.178 Uiso 1 1 calc R A 1
C53 C 0.1563(4) 1.4969(3) 0.5919(4) 0.1285(19) Uani 1 1 d . A 1
H53A H 0.1080 1.4815 0.5306 0.193 Uiso 1 1 calc R A 1
H53B H 0.2151 1.4993 0.5851 0.193 Uiso 1 1 calc R A 1
H53C H 0.1668 1.5582 0.6366 0.193 Uiso 1 1 calc R A 1
C54 C 0.0304(3) 1.4144(3) 0.6364(4) 0.1248(19) Uani 1 1 d . A 1
H54A H -0.0175 1.3956 0.5738 0.187 Uiso 1 1 calc R A 1
H54B H 0.0386 1.4762 0.6780 0.187 Uiso 1 1 calc R A 1
H54C H 0.0103 1.3680 0.6621 0.187 Uiso 1 1 calc R A 1
O21 O 0.0000 1.0000 0.0000 0.183(19) Uani 0.25 6 d SP . .


_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 1.8728(16) . ?
Cu1 N9 1.9365(19) . ?
Cu1 N17 1.988(2) . ?
Cu1 Cl2 2.2185(7) . ?
O1 C2 1.299(3) . ?
C2 C7 1.417(3) . ?
C2 C3 1.425(3) . ?
C3 C4 1.362(3) . ?
C3 C31 1.536(3) . ?
C4 C5 1.407(3) . ?
C4 H4 0.9300 . ?
C5 C6 1.354(3) . ?
C5 C51 1.529(3) . ?
C6 C7 1.401(3) . ?
C6 H6 0.9300 . ?
C7 C8 1.430(3) . ?
C8 N9 1.283(3) . ?
C8 H8 0.9300 . ?
N9 C10 1.464(3) . ?
C10 C11 1.523(4) . ?
C10 H10A 0.9700 . ?
C10 H10B 0.9700 . ?
C11 C12 1.485(4) . ?
C11 H11A 0.9700 . ?
C11 H11B 0.9700 . ?
C12 N17 1.344(3) . ?
C12 C13 1.394(3) . ?
C13 C14 1.369(5) . ?
C13 H13 0.9300 . ?
C14 C15 1.357(5) . ?
C14 H14 0.9300 . ?
C15 C16 1.378(4) . ?
C15 H15 0.9300 . ?
C16 N17 1.347(3) . ?
C16 H16 0.9300 . ?
C31 C32 1.516(4) . ?
C31 C33 1.523(4) . ?
C31 C34 1.531(4) . ?
C32 H32A 0.9600 . ?
C32 H32B 0.9600 . ?
C32 H32C 0.9600 . ?
C33 H33A 0.9600 . ?
C33 H33B 0.9600 . ?
C33 H33C 0.9600 . ?
C34 H34A 0.9600 . ?
C34 H34B 0.9600 . ?
C34 H34C 0.9600 . ?
C51 C54 1.487(4) . ?
C51 C53 1.533(5) . ?
C51 C52 1.538(5) . ?
C52 H52A 0.9600 . ?
C52 H52B 0.9600 . ?
C52 H52C 0.9600 . ?
C53 H53A 0.9600 . ?
C53 H53B 0.9600 . ?
C53 H53C 0.9600 . ?
C54 H54A 0.9600 . ?
C54 H54B 0.9600 . ?
C54 H54C 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
O1 Cu1 N9 94.17(7) . . ?
O1 Cu1 N17 145.22(9) . . ?
N9 Cu1 N17 93.16(8) . . ?
O1 Cu1 Cl2 93.82(5) . . ?
N9 Cu1 Cl2 151.05(6) . . ?
N17 Cu1 Cl2 95.98(6) . . ?
C2 O1 Cu1 129.83(14) . . ?
O1 C2 C7 121.9(2) . . ?
O1 C2 C3 119.80(19) . . ?
C7 C2 C3 118.3(2) . . ?
C4 C3 C2 117.8(2) . . ?
C4 C3 C31 122.4(2) . . ?
C2 C3 C31 119.83(19) . . ?
C3 C4 C5 125.1(2) . . ?
C3 C4 H4 117.5 . . ?
C5 C4 H4 117.5 . . ?
C6 C5 C4 116.4(2) . . ?
C6 C5 C51 123.2(2) . . ?
C4 C5 C51 120.3(2) . . ?
C5 C6 C7 122.4(2) . . ?
C5 C6 H6 118.8 . . ?
C7 C6 H6 118.8 . . ?
C6 C7 C2 120.1(2) . . ?
C6 C7 C8 117.1(2) . . ?
C2 C7 C8 122.9(2) . . ?
N9 C8 C7 128.0(2) . . ?
N9 C8 H8 116.0 . . ?
C7 C8 H8 116.0 . . ?
C8 N9 C10 115.68(19) . . ?
C8 N9 Cu1 123.01(15) . . ?
C10 N9 Cu1 121.30(15) . . ?
N9 C10 C11 113.2(2) . . ?
N9 C10 H10A 108.9 . . ?
C11 C10 H10A 108.9 . . ?
N9 C10 H10B 108.9 . . ?
C11 C10 H10B 108.9 . . ?
H10A C10 H10B 107.8 . . ?
C12 C11 C10 113.8(2) . . ?
C12 C11 H11A 108.8 . . ?
C10 C11 H11A 108.8 . . ?
C12 C11 H11B 108.8 . . ?
C10 C11 H11B 108.8 . . ?
H11A C11 H11B 107.7 . . ?
N17 C12 C13 120.2(3) . . ?
N17 C12 C11 116.7(2) . . ?
C13 C12 C11 123.0(3) . . ?
C14 C13 C12 119.7(3) . . ?
C14 C13 H13 120.2 . . ?
C12 C13 H13 120.2 . . ?
C15 C14 C13 119.8(3) . . ?
C15 C14 H14 120.1 . . ?
C13 C14 H14 120.1 . . ?
C14 C15 C16 119.1(3) . . ?
C14 C15 H15 120.4 . . ?
C16 C15 H15 120.4 . . ?
N17 C16 C15 121.8(3) . . ?
N17 C16 H16 119.1 . . ?
C15 C16 H16 119.1 . . ?
C12 N17 C16 119.4(2) . . ?
C12 N17 Cu1 121.94(17) . . ?
C16 N17 Cu1 118.45(19) . . ?
C32 C31 C33 107.8(2) . . ?
C32 C31 C34 109.4(2) . . ?
C33 C31 C34 107.7(2) . . ?
C32 C31 C3 110.2(2) . . ?
C33 C31 C3 111.8(2) . . ?
C34 C31 C3 109.9(2) . . ?
C31 C32 H32A 109.5 . . ?
C31 C32 H32B 109.5 . . ?
H32A C32 H32B 109.5 . . ?
C31 C32 H32C 109.5 . . ?
H32A C32 H32C 109.5 . . ?
H32B C32 H32C 109.5 . . ?
C31 C33 H33A 109.5 . . ?
C31 C33 H33B 109.5 . . ?
H33A C33 H33B 109.5 . . ?
C31 C33 H33C 109.5 . . ?
H33A C33 H33C 109.5 . . ?
H33B C33 H33C 109.5 . . ?
C31 C34 H34A 109.5 . . ?
C31 C34 H34B 109.5 . . ?
H34A C34 H34B 109.5 . . ?
C31 C34 H34C 109.5 . . ?
H34A C34 H34C 109.5 . . ?
H34B C34 H34C 109.5 . . ?
C54 C51 C5 113.2(2) . . ?
C54 C51 C53 109.0(3) . . ?
C5 C51 C53 110.3(3) . . ?
C54 C51 C52 109.2(3) . . ?
C5 C51 C52 108.9(3) . . ?
C53 C51 C52 105.9(3) . . ?
C51 C52 H52A 109.5 . . ?
C51 C52 H52B 109.5 . . ?
C51 C52 H52C 109.5 . . ?
C51 C53 H53A 109.5 . . ?
C51 C53 H53B 109.5 . . ?
C51 C53 H53C 109.5 . . ?
C51 C54 H54A 109.5 . . ?
C51 C54 H54B 109.5 . . ?
C51 C54 H54C 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
N9 Cu1 O1 C2 -0.6(2) . . . . ?
N17 Cu1 O1 C2 101.0(2) . . . . ?
Cl2 Cu1 O1 C2 -152.78(19) . . . . ?
Cu1 O1 C2 C7 3.5(3) . . . . ?
Cu1 O1 C2 C3 -176.63(16) . . . . ?
O1 C2 C3 C4 -179.2(2) . . . . ?
C7 C2 C3 C4 0.7(3) . . . . ?
O1 C2 C3 C31 0.1(3) . . . . ?
C7 C2 C3 C31 180.0(2) . . . . ?
C2 C3 C4 C5 0.6(4) . . . . ?
C31 C3 C4 C5 -178.6(2) . . . . ?
C3 C4 C5 C6 -1.3(4) . . . . ?
C3 C4 C5 C51 175.9(2) . . . . ?
C4 C5 C6 C7 0.7(4) . . . . ?
C51 C5 C6 C7 -176.4(2) . . . . ?
C5 C6 C7 C2 0.5(4) . . . . ?
C5 C6 C7 C8 -177.6(2) . . . . ?
O1 C2 C7 C6 178.6(2) . . . . ?
C3 C2 C7 C6 -1.2(3) . . . . ?
O1 C2 C7 C8 -3.4(3) . . . . ?
C3 C2 C7 C8 176.8(2) . . . . ?
C6 C7 C8 N9 177.6(2) . . . . ?
C2 C7 C8 N9 -0.5(4) . . . . ?
C7 C8 N9 C10 -175.2(2) . . . . ?
C7 C8 N9 Cu1 3.7(3) . . . . ?
O1 Cu1 N9 C8 -2.87(19) . . . . ?
N17 Cu1 N9 C8 -148.84(18) . . . . ?
Cl2 Cu1 N9 C8 102.8(2) . . . . ?
O1 Cu1 N9 C10 175.98(17) . . . . ?
N17 Cu1 N9 C10 30.01(18) . . . . ?
Cl2 Cu1 N9 C10 -78.4(2) . . . . ?
C8 N9 C10 C11 -172.0(2) . . . . ?
Cu1 N9 C10 C11 9.1(3) . . . . ?
N9 C10 C11 C12 -62.0(3) . . . . ?
C10 C11 C12 N17 61.3(3) . . . . ?
C10 C11 C12 C13 -119.8(3) . . . . ?
N17 C12 C13 C14 -0.4(4) . . . . ?
C11 C12 C13 C14 -179.3(3) . . . . ?
C12 C13 C14 C15 0.4(5) . . . . ?
C13 C14 C15 C16 0.0(5) . . . . ?
C14 C15 C16 N17 -0.4(4) . . . . ?
C13 C12 N17 C16 0.0(4) . . . . ?
C11 C12 N17 C16 178.9(2) . . . . ?
C13 C12 N17 Cu1 174.75(19) . . . . ?
C11 C12 N17 Cu1 -6.3(3) . . . . ?
C15 C16 N17 C12 0.5(4) . . . . ?
C15 C16 N17 Cu1 -174.5(2) . . . . ?
O1 Cu1 N17 C12 -134.98(18) . . . . ?
N9 Cu1 N17 C12 -33.04(19) . . . . ?
Cl2 Cu1 N17 C12 119.45(18) . . . . ?
O1 Cu1 N17 C16 39.9(2) . . . . ?
N9 Cu1 N17 C16 141.80(19) . . . . ?
Cl2 Cu1 N17 C16 -65.70(18) . . . . ?
C4 C3 C31 C32 117.8(3) . . . . ?
C2 C3 C31 C32 -61.5(3) . . . . ?
C4 C3 C31 C33 -2.1(3) . . . . ?
C2 C3 C31 C33 178.6(2) . . . . ?
C4 C3 C31 C34 -121.6(3) . . . . ?
C2 C3 C31 C34 59.1(3) . . . . ?
C6 C5 C51 C54 -5.2(5) . . . . ?
C4 C5 C51 C54 177.8(3) . . . . ?
C6 C5 C51 C53 -127.7(3) . . . . ?
C4 C5 C51 C53 55.3(4) . . . . ?
C6 C5 C51 C52 116.4(3) . . . . ?
C4 C5 C51 C52 -60.6(4) . . . . ?

_diffrn_measured_fraction_theta_max 0.984
_diffrn_reflns_theta_full        27.09
_diffrn_measured_fraction_theta_full 0.984
_refine_diff_density_max         0.551
_refine_diff_density_min         -0.270
_refine_diff_density_rms         0.065
_database_code_depnum_ccdc_archive 'CCDC 950557'
#######################################################################
#
#                 Cambridge Crystallographic Data Centre
#                                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.
#
#  This CIF is provided on the understanding that it is used for bona
#  fide research purposes only. It may contain copyright material
#  of the CCDC or of third parties, and may not be copied or further
#  disseminated in any form, whether machine-readable or not,
#  except for the purpose of generating routine backup copies
#  on your local computer system.
# 
#  For further information on the CCDC, data deposition and
#  data retrieval see:
#                         www.ccdc.cam.ac.uk
#
#  Bona fide researchers may freely download Mercury and enCIFer
#  from this site to visualise CIF-encoded structures and 
#  to carry out CIF format checking respectively.
#
data_e595a

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C24 H32 Cu N2 O3'
_chemical_formula_weight         460.06

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'

_symmetry_cell_setting           Monoclinic
_symmetry_space_group_name_H-M   P2(1)/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                   17.296(2)
_cell_length_b                   11.9783(9)
_cell_length_c                   12.1930(11)
_cell_angle_alpha                90.00
_cell_angle_beta                 105.196(12)
_cell_angle_gamma                90.00
_cell_volume                     2437.8(4)
_cell_formula_units_Z            4
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    4232
_cell_measurement_theta_min      2.0836
_cell_measurement_theta_max      28.0887

_exptl_crystal_description       plate
_exptl_crystal_colour            brown
_exptl_crystal_size_max          0.36
_exptl_crystal_size_mid          0.34
_exptl_crystal_size_min          0.05
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.253
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             972
_exptl_absorpt_coefficient_mu    0.921
_exptl_absorpt_correction_type   analytical
_exptl_absorpt_correction_T_min  0.7354
_exptl_absorpt_correction_T_max  0.9577
_exptl_absorpt_process_details   'Oxford Diffraction CrysAlis'

_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  'Oxford Sapphire CCD'
_diffrn_measurement_method       θ/2θ
_diffrn_detector_area_resol_mean 8.2564
_diffrn_standards_number         0
_diffrn_standards_interval_count 0
_diffrn_standards_interval_time  0
_diffrn_standards_decay_%        0
_diffrn_reflns_number            16433
_diffrn_reflns_av_R_equivalents  0.0812
_diffrn_reflns_av_sigmaI/netI    0.1286
_diffrn_reflns_limit_h_min       -21
_diffrn_reflns_limit_h_max       20
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_l_min       -10
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_theta_min         2.09
_diffrn_reflns_theta_max         28.16
_reflns_number_total             5400
_reflns_number_gt                2468
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'Oxford Diffraction CrysAlis'
_computing_cell_refinement       'Oxford Diffraction CrysAlis'
_computing_data_reduction        'Oxford Diffraction CrysAlis'
_computing_structure_solution    'SHELX-97 (Sheldrick, 1997)'
_computing_structure_refinement  'SHELX-97 (Sheldrick, 1997)'
_computing_molecular_graphics    'PLATON (Spek, 1990)'
_computing_publication_material  'CIFTAB (Sheldrick, 1997)'

_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)+(0.0559P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constrained
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         5400
_refine_ls_number_parameters     298
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1411
_refine_ls_R_factor_gt           0.0516
_refine_ls_wR_factor_ref         0.1249
_refine_ls_wR_factor_gt          0.1022
_refine_ls_goodness_of_fit_ref   0.849
_refine_ls_restrained_S_all      0.849
_refine_ls_shift/su_max          0.129
_refine_ls_shift/su_mean         0.006

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 0.45184(3) -0.00870(3) 0.17566(3) 0.03954(16) Uani 1 1 d . . .
O1 O 0.34833(17) 0.03040(19) 0.0901(2) 0.0461(7) Uani 1 1 d . . .
C1 C 0.2955(3) -0.0359(3) 0.0270(3) 0.0396(10) Uani 1 1 d . . .
C2 C 0.2144(3) -0.0052(4) -0.0048(3) 0.0526(11) Uani 1 1 d . . .
C3 C 0.1599(3) -0.0797(4) -0.0671(3) 0.0659(14) Uani 1 1 d . . .
H3A H 0.1063 -0.0584 -0.0872 0.079 Uiso 1 1 calc R . .
C4 C 0.1783(3) -0.1840(4) -0.1023(3) 0.0618(13) Uani 1 1 d . A .
C5 C 0.2578(3) -0.2108(3) -0.0756(3) 0.0535(12) Uani 1 1 d . . .
H5A H 0.2729 -0.2786 -0.1010 0.064 Uiso 1 1 calc R . .
C6 C 0.3179(3) -0.1403(3) -0.0113(3) 0.0402(10) Uani 1 1 d . . .
C7 C 0.3987(3) -0.1757(3) 0.0087(3) 0.0395(10) Uani 1 1 d . . .
H7A H 0.4076 -0.2401 -0.0288 0.047 Uiso 1 1 calc R . .
N1 N 0.4606(2) -0.1285(2) 0.0727(2) 0.0399(8) Uani 1 1 d . . .
C8 C 0.5394(3) -0.1778(3) 0.0781(3) 0.0501(11) Uani 1 1 d . . .
H8A H 0.5645 -0.1370 0.0278 0.060 Uiso 1 1 calc R . .
H8B H 0.5324 -0.2545 0.0521 0.060 Uiso 1 1 calc R . .
C9 C 0.5934(3) -0.1747(3) 0.1974(3) 0.0494(11) Uani 1 1 d . . .
H9A H 0.5642 -0.2033 0.2494 0.059 Uiso 1 1 calc R . .
H9B H 0.6388 -0.2236 0.2017 0.059 Uiso 1 1 calc R . .
C10 C 0.6233(3) -0.0614(3) 0.2344(3) 0.0441(11) Uani 1 1 d . . .
C11 C 0.7042(3) -0.0381(4) 0.2749(3) 0.0576(12) Uani 1 1 d . . .
H11A H 0.7416 -0.0950 0.2798 0.069 Uiso 1 1 calc R . .
C12 C 0.7298(3) 0.0682(4) 0.3078(4) 0.0598(13) Uani 1 1 d . . .
H12A H 0.7840 0.0841 0.3351 0.072 Uiso 1 1 calc R . .
C13 C 0.6734(3) 0.1501(4) 0.2994(3) 0.0529(12) Uani 1 1 d . . .
H13A H 0.6888 0.2230 0.3208 0.063 Uiso 1 1 calc R . .
C14 C 0.5948(3) 0.1236(3) 0.2596(3) 0.0460(11) Uani 1 1 d . . .
H14A H 0.5569 0.1798 0.2539 0.055 Uiso 1 1 calc R . .
N2 N 0.5691(2) 0.0191(2) 0.2279(2) 0.0397(8) Uani 1 1 d . . .
C15 C 0.1874(3) 0.1092(4) 0.0292(4) 0.0628(13) Uani 1 1 d . . .
C16 C 0.2298(4) 0.2019(4) -0.0179(4) 0.0903(19) Uani 1 1 d . . .
H16A H 0.2157 0.2729 0.0079 0.108 Uiso 1 1 calc R . .
H16B H 0.2137 0.1998 -0.0994 0.108 Uiso 1 1 calc R . .
H16C H 0.2867 0.1914 0.0082 0.108 Uiso 1 1 calc R . .
C17 C 0.2081(3) 0.1195(3) 0.1578(4) 0.0755(16) Uani 1 1 d . . .
H17A H 0.1864 0.1878 0.1782 0.091 Uiso 1 1 calc R . .
H17B H 0.2653 0.1196 0.1877 0.091 Uiso 1 1 calc R . .
H17C H 0.1858 0.0574 0.1888 0.091 Uiso 1 1 calc R . .
C18 C 0.0976(4) 0.1271(5) -0.0151(5) 0.118(2) Uani 1 1 d . . .
H18A H 0.0837 0.1991 0.0086 0.141 Uiso 1 1 calc R . .
H18B H 0.0697 0.0702 0.0147 0.141 Uiso 1 1 calc R . .
H18C H 0.0827 0.1233 -0.0966 0.141 Uiso 1 1 calc R . .
C19 C 0.1141(4) -0.2642(6) -0.1698(5) 0.092(2) Uani 1 1 d . . .
C20 C 0.1414(19) -0.340(3) -0.231(2) 0.23(2) Uani 0.55 1 d P A 1
H20A H 0.1389 -0.3090 -0.3050 0.281 Uiso 0.55 1 calc PR A 1
H20B H 0.1089 -0.4055 -0.2398 0.281 Uiso 0.55 1 calc PR A 1
H20C H 0.1958 -0.3581 -0.1937 0.281 Uiso 0.55 1 calc PR A 1
C21 C 0.0677(10) -0.3004(13) -0.0997(13) 0.105(5) Uani 0.55 1 d P A 1
H21A H 0.0294 -0.2437 -0.0954 0.126 Uiso 0.55 1 calc PR A 1
H21B H 0.1015 -0.3148 -0.0251 0.126 Uiso 0.55 1 calc PR A 1
H21C H 0.0401 -0.3676 -0.1302 0.126 Uiso 0.55 1 calc PR A 1
C22 C 0.0581(13) -0.1885(17) -0.2656(13) 0.159(10) Uani 0.55 1 d P A 1
H22A H 0.0733 -0.1116 -0.2520 0.191 Uiso 0.55 1 calc PR A 1
H22B H 0.0033 -0.1976 -0.2638 0.191 Uiso 0.55 1 calc PR A 1
H22C H 0.0639 -0.2105 -0.3387 0.191 Uiso 0.55 1 calc PR A 1
C20B C 0.137(2) -0.312(3) -0.2761(17) 0.115(9) Uani 0.45 1 d P A 2
H20D H 0.1269 -0.2558 -0.3346 0.138 Uiso 0.45 1 calc PR A 2
H20E H 0.1043 -0.3762 -0.3032 0.138 Uiso 0.45 1 calc PR A 2
H20F H 0.1921 -0.3321 -0.2561 0.138 Uiso 0.45 1 calc PR A 2
C21B C 0.1292(16) -0.3869(17) -0.1018(15) 0.161(10) Uani 0.45 1 d P A 2
H21D H 0.1774 -0.3832 -0.0409 0.194 Uiso 0.45 1 calc PR A 2
H21E H 0.1344 -0.4447 -0.1540 0.194 Uiso 0.45 1 calc PR A 2
H21F H 0.0846 -0.4033 -0.0714 0.194 Uiso 0.45 1 calc PR A 2
C22B C 0.0309(15) -0.231(3) -0.182(3) 0.30(3) Uani 0.45 1 d P A 2
H22D H 0.0238 -0.1549 -0.2060 0.358 Uiso 0.45 1 calc PR A 2
H22E H 0.0182 -0.2398 -0.1106 0.358 Uiso 0.45 1 calc PR A 2
H22F H -0.0038 -0.2780 -0.2380 0.358 Uiso 0.45 1 calc PR A 2
O2 O 0.43304(17) 0.06787(18) 0.3083(2) 0.0440(7) Uani 1 1 d . . .
O3 O 0.4116(2) -0.1081(2) 0.3341(2) 0.0745(12) Uani 1 1 d . . .
C23 C 0.4097(3) -0.0103(3) 0.3614(3) 0.0456(10) Uani 1 1 d . . .
C24 C 0.3809(3) 0.0222(4) 0.4621(4) 0.0791(16) Uani 1 1 d . . .
H24A H 0.3623 -0.0430 0.4934 0.095 Uiso 1 1 calc R . .
H24B H 0.3378 0.0747 0.4392 0.095 Uiso 1 1 calc R . .
H24C H 0.4240 0.0557 0.5185 0.095 Uiso 1 1 calc R . .


_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 1.880(3) . ?
Cu1 N1 1.938(3) . ?
Cu1 O2 1.960(2) . ?
Cu1 N2 1.989(3) . ?
O1 C1 1.300(4) . ?
C1 C2 1.403(6) . ?
C1 C6 1.423(5) . ?
C2 C3 1.374(6) . ?
C2 C15 1.539(6) . ?
C3 C4 1.385(6) . ?
C3 H3A 0.9300 . ?
C4 C5 1.365(6) . ?
C4 C19 1.534(7) . ?
C5 C6 1.408(5) . ?
C5 H5A 0.9300 . ?
C6 C7 1.419(6) . ?
C7 N1 1.280(5) . ?
C7 H7A 0.9300 . ?
N1 C8 1.472(5) . ?
C8 C9 1.509(5) . ?
C8 H8A 0.9700 . ?
C8 H8B 0.9700 . ?
C9 C10 1.480(5) . ?
C9 H9A 0.9700 . ?
C9 H9B 0.9700 . ?
C10 N2 1.332(5) . ?
C10 C11 1.385(6) . ?
C11 C12 1.373(6) . ?
C11 H11A 0.9300 . ?
C12 C13 1.368(6) . ?
C12 H12A 0.9300 . ?
C13 C14 1.356(6) . ?
C13 H13A 0.9300 . ?
C14 N2 1.350(4) . ?
C14 H14A 0.9300 . ?
C15 C18 1.520(7) . ?
C15 C17 1.519(6) . ?
C15 C16 1.523(7) . ?
C16 H16A 0.9600 . ?
C16 H16B 0.9600 . ?
C16 H16C 0.9600 . ?
C17 H17A 0.9600 . ?
C17 H17B 0.9600 . ?
C17 H17C 0.9600 . ?
C18 H18A 0.9600 . ?
C18 H18B 0.9600 . ?
C18 H18C 0.9600 . ?
C19 C20 1.34(3) . ?
C19 C21 1.386(15) . ?
C19 C22B 1.46(3) . ?
C19 C20B 1.55(3) . ?
C19 C22 1.59(2) . ?
C19 C21B 1.675(19) . ?
C20 H20A 0.9600 . ?
C20 H20B 0.9600 . ?
C20 H20C 0.9600 . ?
C21 H21A 0.9600 . ?
C21 H21B 0.9600 . ?
C21 H21C 0.9600 . ?
C22 H22A 0.9600 . ?
C22 H22B 0.9600 . ?
C22 H22C 0.9600 . ?
C20B H20D 0.9600 . ?
C20B H20E 0.9600 . ?
C20B H20F 0.9600 . ?
C21B H21D 0.9600 . ?
C21B H21E 0.9600 . ?
C21B H21F 0.9600 . ?
C22B H22D 0.9600 . ?
C22B H22E 0.9600 . ?
C22B H22F 0.9600 . ?
O2 C23 1.263(4) . ?
O3 C23 1.220(4) . ?
C23 C24 1.493(5) . ?
C24 H24A 0.9600 . ?
C24 H24B 0.9600 . ?
C24 H24C 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
O1 Cu1 N1 92.85(13) . . ?
O1 Cu1 O2 90.09(11) . . ?
N1 Cu1 O2 159.92(11) . . ?
O1 Cu1 N2 151.54(11) . . ?
N1 Cu1 N2 94.89(14) . . ?
O2 Cu1 N2 91.90(12) . . ?
C1 O1 Cu1 126.5(2) . . ?
O1 C1 C2 120.0(3) . . ?
O1 C1 C6 121.5(4) . . ?
C2 C1 C6 118.6(4) . . ?
C3 C2 C1 118.3(4) . . ?
C3 C2 C15 121.0(4) . . ?
C1 C2 C15 120.8(4) . . ?
C2 C3 C4 125.3(5) . . ?
C2 C3 H3A 117.4 . . ?
C4 C3 H3A 117.4 . . ?
C5 C4 C3 115.9(4) . . ?
C5 C4 C19 121.5(5) . . ?
C3 C4 C19 122.5(5) . . ?
C4 C5 C6 122.8(4) . . ?
C4 C5 H5A 118.6 . . ?
C6 C5 H5A 118.6 . . ?
C5 C6 C7 117.8(4) . . ?
C5 C6 C1 119.0(4) . . ?
C7 C6 C1 123.1(4) . . ?
N1 C7 C6 127.0(4) . . ?
N1 C7 H7A 116.5 . . ?
C6 C7 H7A 116.5 . . ?
C7 N1 C8 117.9(3) . . ?
C7 N1 Cu1 121.8(3) . . ?
C8 N1 Cu1 119.8(3) . . ?
N1 C8 C9 111.4(3) . . ?
N1 C8 H8A 109.3 . . ?
C9 C8 H8A 109.3 . . ?
N1 C8 H8B 109.3 . . ?
C9 C8 H8B 109.3 . . ?
H8A C8 H8B 108.0 . . ?
C10 C9 C8 113.2(3) . . ?
C10 C9 H9A 108.9 . . ?
C8 C9 H9A 108.9 . . ?
C10 C9 H9B 108.9 . . ?
C8 C9 H9B 108.9 . . ?
H9A C9 H9B 107.7 . . ?
N2 C10 C11 120.3(4) . . ?
N2 C10 C9 117.5(4) . . ?
C11 C10 C9 122.2(4) . . ?
C12 C11 C10 120.6(4) . . ?
C12 C11 H11A 119.7 . . ?
C10 C11 H11A 119.7 . . ?
C13 C12 C11 118.4(5) . . ?
C13 C12 H12A 120.8 . . ?
C11 C12 H12A 120.8 . . ?
C14 C13 C12 119.1(4) . . ?
C14 C13 H13A 120.4 . . ?
C12 C13 H13A 120.4 . . ?
N2 C14 C13 122.9(4) . . ?
N2 C14 H14A 118.5 . . ?
C13 C14 H14A 118.5 . . ?
C10 N2 C14 118.7(4) . . ?
C10 N2 Cu1 122.7(3) . . ?
C14 N2 Cu1 118.6(3) . . ?
C18 C15 C17 107.4(4) . . ?
C18 C15 C16 108.2(4) . . ?
C17 C15 C16 108.9(4) . . ?
C18 C15 C2 112.6(4) . . ?
C17 C15 C2 110.1(4) . . ?
C16 C15 C2 109.7(4) . . ?
C15 C16 H16A 109.5 . . ?
C15 C16 H16B 109.5 . . ?
H16A C16 H16B 109.5 . . ?
C15 C16 H16C 109.5 . . ?
H16A C16 H16C 109.5 . . ?
H16B C16 H16C 109.5 . . ?
C15 C17 H17A 109.5 . . ?
C15 C17 H17B 109.5 . . ?
H17A C17 H17B 109.5 . . ?
C15 C17 H17C 109.5 . . ?
H17A C17 H17C 109.5 . . ?
H17B C17 H17C 109.5 . . ?
C15 C18 H18A 109.5 . . ?
C15 C18 H18B 109.5 . . ?
H18A C18 H18B 109.5 . . ?
C15 C18 H18C 109.5 . . ?
H18A C18 H18C 109.5 . . ?
H18B C18 H18C 109.5 . . ?
C20 C19 C21 118.8(14) . . ?
C20 C19 C22B 127.3(15) . . ?
C21 C19 C22B 55.5(18) . . ?
C20 C19 C20B 23(2) . . ?
C21 C19 C20B 135.3(14) . . ?
C22B C19 C20B 117.8(19) . . ?
C20 C19 C4 114.3(12) . . ?
C21 C19 C4 108.6(7) . . ?
C22B C19 C4 116.2(11) . . ?
C20B C19 C4 111.9(14) . . ?
C20 C19 C22 102.1(16) . . ?
C21 C19 C22 106.9(11) . . ?
C22B C19 C22 51.5(19) . . ?
C20B C19 C22 80.4(15) . . ?
C4 C19 C22 104.6(7) . . ?
C20 C19 C21B 69.7(14) . . ?
C21 C19 C21B 57.4(10) . . ?
C22B C19 C21B 108(2) . . ?
C20B C19 C21B 93.0(15) . . ?
C4 C19 C21B 106.7(7) . . ?
C22 C19 C21B 148.2(9) . . ?
C19 C20 H20A 109.5 . . ?
C19 C20 H20B 109.5 . . ?
H20A C20 H20B 109.5 . . ?
C19 C20 H20C 109.4 . . ?
H20A C20 H20C 109.5 . . ?
H20B C20 H20C 109.5 . . ?
C19 C21 H21A 109.5 . . ?
C19 C21 H21B 109.5 . . ?
H21A C21 H21B 109.5 . . ?
C19 C21 H21C 109.5 . . ?
H21A C21 H21C 109.5 . . ?
H21B C21 H21C 109.5 . . ?
C19 C22 H22A 109.5 . . ?
C19 C22 H22B 109.5 . . ?
H22A C22 H22B 109.5 . . ?
C19 C22 H22C 109.5 . . ?
H22A C22 H22C 109.5 . . ?
H22B C22 H22C 109.5 . . ?
C19 C20B H20D 109.3 . . ?
C19 C20B H20E 109.5 . . ?
H20D C20B H20E 109.5 . . ?
C19 C20B H20F 109.6 . . ?
H20D C20B H20F 109.5 . . ?
H20E C20B H20F 109.5 . . ?
C19 C21B H21D 109.5 . . ?
C19 C21B H21E 109.5 . . ?
H21D C21B H21E 109.5 . . ?
C19 C21B H21F 109.5 . . ?
H21D C21B H21F 109.5 . . ?
H21E C21B H21F 109.5 . . ?
C19 C22B H22D 109.5 . . ?
C19 C22B H22E 109.5 . . ?
H22D C22B H22E 109.5 . . ?
C19 C22B H22F 109.5 . . ?
H22D C22B H22F 109.5 . . ?
H22E C22B H22F 109.5 . . ?
C23 O2 Cu1 102.7(2) . . ?
O3 C23 O2 122.5(3) . . ?
O3 C23 C24 120.9(3) . . ?
O2 C23 C24 116.6(3) . . ?
C23 C24 H24A 109.5 . . ?
C23 C24 H24B 109.5 . . ?
H24A C24 H24B 109.5 . . ?
C23 C24 H24C 109.5 . . ?
H24A C24 H24C 109.5 . . ?
H24B C24 H24C 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
N1 Cu1 O1 C1 28.7(3) . . . . ?
O2 Cu1 O1 C1 -131.4(3) . . . . ?
N2 Cu1 O1 C1 134.4(3) . . . . ?
Cu1 O1 C1 C2 161.2(3) . . . . ?
Cu1 O1 C1 C6 -18.7(5) . . . . ?
O1 C1 C2 C3 -177.0(3) . . . . ?
C6 C1 C2 C3 3.0(5) . . . . ?
O1 C1 C2 C15 3.1(5) . . . . ?
C6 C1 C2 C15 -176.9(3) . . . . ?
C1 C2 C3 C4 -0.3(7) . . . . ?
C15 C2 C3 C4 179.5(4) . . . . ?
C2 C3 C4 C5 -2.7(7) . . . . ?
C2 C3 C4 C19 178.7(5) . . . . ?
C3 C4 C5 C6 3.1(6) . . . . ?
C19 C4 C5 C6 -178.3(4) . . . . ?
C4 C5 C6 C7 -178.4(4) . . . . ?
C4 C5 C6 C1 -0.6(6) . . . . ?
O1 C1 C6 C5 177.4(3) . . . . ?
C2 C1 C6 C5 -2.5(5) . . . . ?
O1 C1 C6 C7 -4.9(5) . . . . ?
C2 C1 C6 C7 175.1(3) . . . . ?
C5 C6 C7 N1 -173.5(3) . . . . ?
C1 C6 C7 N1 8.8(6) . . . . ?
C6 C7 N1 C8 -178.0(3) . . . . ?
C6 C7 N1 Cu1 10.3(5) . . . . ?
O1 Cu1 N1 C7 -23.6(3) . . . . ?
O2 Cu1 N1 C7 74.5(5) . . . . ?
N2 Cu1 N1 C7 -176.2(3) . . . . ?
O1 Cu1 N1 C8 164.9(3) . . . . ?
O2 Cu1 N1 C8 -97.1(5) . . . . ?
N2 Cu1 N1 C8 12.3(3) . . . . ?
C7 N1 C8 C9 -140.5(3) . . . . ?
Cu1 N1 C8 C9 31.3(4) . . . . ?
N1 C8 C9 C10 -72.8(5) . . . . ?
C8 C9 C10 N2 54.8(5) . . . . ?
C8 C9 C10 C11 -125.4(4) . . . . ?
N2 C10 C11 C12 -0.6(6) . . . . ?
C9 C10 C11 C12 179.6(4) . . . . ?
C10 C11 C12 C13 -0.1(6) . . . . ?
C11 C12 C13 C14 0.2(6) . . . . ?
C12 C13 C14 N2 0.3(6) . . . . ?
C11 C10 N2 C14 1.1(5) . . . . ?
C9 C10 N2 C14 -179.1(3) . . . . ?
C11 C10 N2 Cu1 -177.9(3) . . . . ?
C9 C10 N2 Cu1 1.9(4) . . . . ?
C13 C14 N2 C10 -1.0(5) . . . . ?
C13 C14 N2 Cu1 178.1(3) . . . . ?
O1 Cu1 N2 C10 -136.6(3) . . . . ?
N1 Cu1 N2 C10 -31.3(3) . . . . ?
O2 Cu1 N2 C10 129.7(3) . . . . ?
O1 Cu1 N2 C14 44.5(4) . . . . ?
N1 Cu1 N2 C14 149.7(3) . . . . ?
O2 Cu1 N2 C14 -49.2(3) . . . . ?
C3 C2 C15 C18 -0.9(6) . . . . ?
C1 C2 C15 C18 179.0(4) . . . . ?
C3 C2 C15 C17 118.9(5) . . . . ?
C1 C2 C15 C17 -61.3(6) . . . . ?
C3 C2 C15 C16 -121.4(5) . . . . ?
C1 C2 C15 C16 58.5(5) . . . . ?
C5 C4 C19 C20 -21.8(18) . . . . ?
C3 C4 C19 C20 156.7(17) . . . . ?
C5 C4 C19 C21 113.5(10) . . . . ?
C3 C4 C19 C21 -68.0(12) . . . . ?
C5 C4 C19 C22B 173(2) . . . . ?
C3 C4 C19 C22B -8(3) . . . . ?
C5 C4 C19 C20B -47.2(15) . . . . ?
C3 C4 C19 C20B 131.2(14) . . . . ?
C5 C4 C19 C22 -132.6(10) . . . . ?
C3 C4 C19 C22 45.9(11) . . . . ?
C5 C4 C19 C21B 53.0(13) . . . . ?
C3 C4 C19 C21B -128.5(13) . . . . ?
O1 Cu1 O2 C23 94.9(3) . . . . ?
N1 Cu1 O2 C23 -3.7(5) . . . . ?
N2 Cu1 O2 C23 -113.5(3) . . . . ?
Cu1 O2 C23 O3 8.1(5) . . . . ?
Cu1 O2 C23 C24 -173.2(3) . . . . ?

_diffrn_measured_fraction_theta_max 0.905
_diffrn_reflns_theta_full        25.00
_diffrn_measured_fraction_theta_full 1.000
_refine_diff_density_max         0.537
_refine_diff_density_min         -0.513
_refine_diff_density_rms         0.067
_database_code_depnum_ccdc_archive 'CCDC 986880'
