# Electronic Supplementary Material (ESI) for RSC Advances.
# 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.
#
data_exp_1975

_audit_creation_method           SHELXL-97
_chemical_name_systematic        Ligand
_chemical_name_common            L1
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C34 H44 N2 O'
_chemical_formula_weight         496.71

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'

_symmetry_cell_setting           ?
_symmetry_space_group_name_H-M   P21/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                   11.4955(11)
_cell_length_b                   10.9564(13)
_cell_length_c                   23.216(2)
_cell_angle_alpha                90.00
_cell_angle_beta                 95.880(9)
_cell_angle_gamma                90.00
_cell_volume                     2908.7(5)
_cell_formula_units_Z            4
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    ?
_cell_measurement_theta_min      ?
_cell_measurement_theta_max      ?

_exptl_crystal_description       ?
_exptl_crystal_colour            White
_exptl_crystal_size_max          0.4
_exptl_crystal_size_mid          0.3
_exptl_crystal_size_min          0.2
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.134
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1080
_exptl_absorpt_coefficient_mu    0.067
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.47891
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_process_details   ?

_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  ?
_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            11060
_diffrn_reflns_av_R_equivalents  0.0558
_diffrn_reflns_av_sigmaI/netI    0.1137
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_l_min       -27
_diffrn_reflns_limit_l_max       24
_diffrn_reflns_theta_min         3.22
_diffrn_reflns_theta_max         25.00
_reflns_number_total             5110
_reflns_number_gt                2500
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    ?
_computing_publication_material  ?

_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)+(0.0000P)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         5110
_refine_ls_number_parameters     343
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1488
_refine_ls_R_factor_gt           0.0701
_refine_ls_wR_factor_ref         0.1002
_refine_ls_wR_factor_gt          0.0808
_refine_ls_goodness_of_fit_ref   1.174
_refine_ls_restrained_S_all      1.174
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
O1 O 0.58100(16) 0.7923(2) 0.44587(9) 0.0457(6) Uani 1 1 d . . .
H1 H 0.6127 0.8105 0.4780 0.069 Uiso 1 1 calc R . .
N2 N 0.8133(2) 0.8222(2) 0.52135(10) 0.0341(7) Uani 1 1 d . . .
C8 C 0.8071(3) 0.8637(3) 0.31971(13) 0.0347(8) Uani 1 1 d . . .
C10 C 0.6257(3) 0.7731(3) 0.34807(13) 0.0355(8) Uani 1 1 d . . .
C4 C 0.8168(2) 0.8643(3) 0.58132(12) 0.0417(9) Uani 1 1 d . . .
H4A H 0.8747 0.9286 0.5878 0.050 Uiso 1 1 calc R . .
H4B H 0.8406 0.7973 0.6072 0.050 Uiso 1 1 calc R . .
N1 N 0.6006(2) 0.8369(3) 0.57098(11) 0.0419(7) Uani 1 1 d . . .
C6 C 0.7610(3) 0.8782(3) 0.41904(13) 0.0338(8) Uani 1 1 d . . .
C9 C 0.7024(2) 0.8000(3) 0.30707(13) 0.0375(9) Uani 1 1 d . . .
H9 H 0.6827 0.7742 0.2692 0.045 Uiso 1 1 calc R . .
C11 C 0.6569(3) 0.8136(3) 0.40490(13) 0.0343(8) Uani 1 1 d . . .
C16 C 0.5103(3) 0.7049(3) 0.33056(14) 0.0418(9) Uani 1 1 d . . .
C5 C 0.7922(2) 0.9229(3) 0.47972(12) 0.0373(8) Uani 1 1 d . . .
H5A H 0.8619 0.9731 0.4808 0.045 Uiso 1 1 calc R . .
H5B H 0.7292 0.9735 0.4910 0.045 Uiso 1 1 calc R . .
C12 C 0.8850(3) 0.8912(3) 0.27111(14) 0.0415(9) Uani 1 1 d . . .
C2 C 0.4894(3) 0.8974(3) 0.57859(15) 0.0678(12) Uani 1 1 d . . .
H2A H 0.4258 0.8486 0.5613 0.102 Uiso 1 1 calc R . .
H2B H 0.4875 0.9761 0.5603 0.102 Uiso 1 1 calc R . .
H2C H 0.4821 0.9072 0.6192 0.102 Uiso 1 1 calc R . .
C1 C 0.6044(3) 0.7147(3) 0.59628(15) 0.0657(12) Uani 1 1 d . . .
H1A H 0.6765 0.6756 0.5895 0.099 Uiso 1 1 calc R . .
H1B H 0.5398 0.6675 0.5788 0.099 Uiso 1 1 calc R . .
H1C H 0.5994 0.7207 0.6372 0.099 Uiso 1 1 calc R . .
C17 C 0.5000(3) 0.6620(3) 0.26688(14) 0.0632(12) Uani 1 1 d . . .
H17A H 0.5637 0.6081 0.2612 0.095 Uiso 1 1 calc R . .
H17B H 0.5027 0.7315 0.2419 0.095 Uiso 1 1 calc R . .
H17C H 0.4272 0.6197 0.2579 0.095 Uiso 1 1 calc R . .
C7 C 0.8339(3) 0.9002(3) 0.37621(13) 0.0364(8) Uani 1 1 d . . .
H7 H 0.9038 0.9414 0.3861 0.044 Uiso 1 1 calc R . .
C3 C 0.6983(3) 0.9125(3) 0.59557(13) 0.0444(9) Uani 1 1 d . . .
H3A H 0.6976 0.9157 0.6373 0.053 Uiso 1 1 calc R . .
H3B H 0.6877 0.9950 0.5808 0.053 Uiso 1 1 calc R . .
C18 C 0.4058(2) 0.7905(3) 0.33715(14) 0.0578(11) Uani 1 1 d . . .
H18A H 0.3341 0.7485 0.3253 0.087 Uiso 1 1 calc R . .
H18B H 0.4118 0.8615 0.3134 0.087 Uiso 1 1 calc R . .
H18C H 0.4066 0.8149 0.3769 0.087 Uiso 1 1 calc R . .
C20 C 0.9203(2) 0.7567(3) 0.51013(13) 0.0402(9) Uani 1 1 d . . .
H20A H 0.9855 0.8132 0.5152 0.048 Uiso 1 1 calc R . .
H20B H 0.9124 0.7305 0.4700 0.048 Uiso 1 1 calc R . .
C29 C 0.9117(3) 0.4335(3) 0.57339(14) 0.0411(9) Uani 1 1 d . . .
C31 C 0.7411(3) 0.3282(4) 0.52797(17) 0.0642(12) Uani 1 1 d . . .
H31 H 0.6943 0.2589 0.5240 0.077 Uiso 1 1 calc R . .
C25 C 1.2482(3) 0.6378(4) 0.67188(16) 0.0650(12) Uani 1 1 d . . .
H25 H 1.3141 0.6357 0.6987 0.078 Uiso 1 1 calc R . .
C21 C 0.9493(3) 0.6468(3) 0.54798(13) 0.0357(8) Uani 1 1 d . . .
C24 C 1.2159(3) 0.7475(4) 0.64275(16) 0.0587(11) Uani 1 1 d . . .
H24 H 1.2601 0.8176 0.6510 0.070 Uiso 1 1 calc R . .
C34 C 0.8797(3) 0.5412(3) 0.54016(13) 0.0370(9) Uani 1 1 d . . .
C32 C 0.7096(3) 0.4334(4) 0.49434(16) 0.0596(11) Uani 1 1 d . . .
H32 H 0.6426 0.4324 0.4683 0.072 Uiso 1 1 calc R . .
C26 C 1.1836(3) 0.5358(4) 0.66098(15) 0.0556(11) Uani 1 1 d . . .
H26 H 1.2059 0.4636 0.6801 0.067 Uiso 1 1 calc R . .
C23 C 1.1206(3) 0.7523(3) 0.60251(14) 0.0488(10) Uani 1 1 d . . .
H23 H 1.1019 0.8253 0.5833 0.059 Uiso 1 1 calc R . .
C19 C 0.5003(3) 0.5898(3) 0.36820(15) 0.0578(11) Uani 1 1 d . . .
H19A H 0.5006 0.6133 0.4081 0.087 Uiso 1 1 calc R . .
H19B H 0.5654 0.5368 0.3640 0.087 Uiso 1 1 calc R . .
H19C H 0.4287 0.5479 0.3559 0.087 Uiso 1 1 calc R . .
C27 C 1.0814(3) 0.5375(3) 0.62033(14) 0.0403(9) Uani 1 1 d . . .
C30 C 0.8388(3) 0.3280(3) 0.56573(15) 0.0561(11) Uani 1 1 d . . .
H30 H 0.8588 0.2579 0.5871 0.067 Uiso 1 1 calc R . .
C22 C 1.0486(3) 0.6467(3) 0.58929(13) 0.0370(9) Uani 1 1 d . . .
C33 C 0.7769(3) 0.5361(3) 0.49994(14) 0.0460(9) Uani 1 1 d . . .
H33 H 0.7556 0.6040 0.4772 0.055 Uiso 1 1 calc R . .
C14 C 0.8213(3) 0.9815(4) 0.22903(16) 0.0912(16) Uani 1 1 d . . .
H14A H 0.7492 0.9461 0.2124 0.137 Uiso 1 1 calc R . .
H14B H 0.8695 1.0005 0.1988 0.137 Uiso 1 1 calc R . .
H14C H 0.8052 1.0550 0.2493 0.137 Uiso 1 1 calc R . .
C28 C 1.0131(3) 0.4339(3) 0.61144(14) 0.0451(9) Uani 1 1 d . . .
H28 H 1.0357 0.3628 0.6314 0.054 Uiso 1 1 calc R . .
C13 C 1.0022(3) 0.9470(4) 0.29459(15) 0.0854(15) Uani 1 1 d . . .
H13A H 0.9889 1.0226 0.3138 0.128 Uiso 1 1 calc R . .
H13B H 1.0484 0.9620 0.2631 0.128 Uiso 1 1 calc R . .
H13C H 1.0430 0.8916 0.3216 0.128 Uiso 1 1 calc R . .
C15 C 0.9101(3) 0.7756(3) 0.23820(15) 0.0816(14) Uani 1 1 d . . .
H15A H 0.9497 0.7177 0.2644 0.122 Uiso 1 1 calc R . .
H15B H 0.9587 0.7950 0.2082 0.122 Uiso 1 1 calc R . .
H15C H 0.8379 0.7410 0.2213 0.122 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
O1 C11 1.375(3) . ?
N2 C4 1.463(3) . ?
N2 C20 1.471(3) . ?
N2 C5 1.470(3) . ?
C8 C7 1.376(4) . ?
C8 C9 1.396(4) . ?
C8 C12 1.540(4) . ?
C10 C9 1.394(4) . ?
C10 C11 1.403(4) . ?
C10 C16 1.541(4) . ?
C4 C3 1.529(3) . ?
N1 C2 1.467(3) . ?
N1 C3 1.463(3) . ?
N1 C1 1.461(4) . ?
C6 C7 1.385(4) . ?
C6 C11 1.400(4) . ?
C6 C5 1.500(4) . ?
C16 C18 1.544(4) . ?
C16 C17 1.544(4) . ?
C16 C19 1.545(4) . ?
C12 C15 1.522(4) . ?
C12 C13 1.528(4) . ?
C12 C14 1.525(4) . ?
C20 C21 1.508(4) . ?
C29 C28 1.389(4) . ?
C29 C30 1.429(4) . ?
C29 C34 1.436(4) . ?
C31 C30 1.351(4) . ?
C31 C32 1.419(4) . ?
C25 C26 1.351(4) . ?
C25 C24 1.410(5) . ?
C21 C34 1.407(4) . ?
C21 C22 1.414(4) . ?
C24 C23 1.366(4) . ?
C34 C33 1.431(4) . ?
C32 C33 1.364(4) . ?
C26 C27 1.430(4) . ?
C23 C22 1.436(4) . ?
C27 C28 1.384(4) . ?
C27 C22 1.427(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
C4 N2 C20 112.4(2) . . ?
C4 N2 C5 112.1(2) . . ?
C20 N2 C5 109.5(2) . . ?
C7 C8 C9 116.7(3) . . ?
C7 C8 C12 123.5(3) . . ?
C9 C8 C12 119.8(3) . . ?
C9 C10 C11 117.1(3) . . ?
C9 C10 C16 120.7(3) . . ?
C11 C10 C16 122.1(3) . . ?
N2 C4 C3 112.1(2) . . ?
C2 N1 C3 109.9(3) . . ?
C2 N1 C1 110.9(3) . . ?
C3 N1 C1 111.8(3) . . ?
C7 C6 C11 119.0(3) . . ?
C7 C6 C5 120.9(3) . . ?
C11 C6 C5 120.1(3) . . ?
C10 C9 C8 123.7(3) . . ?
O1 C11 C6 120.7(3) . . ?
O1 C11 C10 118.5(3) . . ?
C6 C11 C10 120.7(3) . . ?
C18 C16 C10 109.7(3) . . ?
C18 C16 C17 107.2(3) . . ?
C10 C16 C17 112.3(3) . . ?
C18 C16 C19 109.7(3) . . ?
C10 C16 C19 111.0(3) . . ?
C17 C16 C19 106.9(3) . . ?
N2 C5 C6 112.3(3) . . ?
C15 C12 C13 107.8(3) . . ?
C15 C12 C14 108.8(3) . . ?
C13 C12 C14 108.5(3) . . ?
C15 C12 C8 111.0(3) . . ?
C13 C12 C8 112.0(3) . . ?
C14 C12 C8 108.6(3) . . ?
C8 C7 C6 122.8(3) . . ?
N1 C3 C4 112.7(3) . . ?
N2 C20 C21 115.2(2) . . ?
C28 C29 C30 121.7(3) . . ?
C28 C29 C34 119.4(3) . . ?
C30 C29 C34 118.9(3) . . ?
C30 C31 C32 120.5(4) . . ?
C26 C25 C24 120.2(4) . . ?
C34 C21 C22 119.7(3) . . ?
C34 C21 C20 119.5(3) . . ?
C22 C21 C20 120.7(3) . . ?
C23 C24 C25 120.9(4) . . ?
C21 C34 C33 122.5(3) . . ?
C21 C34 C29 119.7(3) . . ?
C33 C34 C29 117.9(3) . . ?
C33 C32 C31 120.5(4) . . ?
C25 C26 C27 120.7(4) . . ?
C24 C23 C22 121.3(4) . . ?
C28 C27 C22 119.7(3) . . ?
C28 C27 C26 120.2(3) . . ?
C22 C27 C26 120.1(3) . . ?
C31 C30 C29 121.1(4) . . ?
C21 C22 C27 119.7(3) . . ?
C21 C22 C23 123.5(3) . . ?
C27 C22 C23 116.8(3) . . ?
C32 C33 C34 121.1(3) . . ?
C27 C28 C29 121.6(3) . . ?

_diffrn_measured_fraction_theta_max 0.998
_diffrn_reflns_theta_full        25.00
_diffrn_measured_fraction_theta_full 0.998
_refine_diff_density_max         0.221
_refine_diff_density_min         -0.219
_refine_diff_density_rms         0.045
_database_code_depnum_ccdc_archive 'CCDC 1009929'
#######################################################################
#
#                 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_complex1

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C36 H46 Cu N2 O3'
_chemical_formula_weight         618.29

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           ?
_symmetry_space_group_name_H-M   C2/c

loop_
_symmetry_equiv_pos_as_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                   28.2038(9)
_cell_length_b                   12.6258(4)
_cell_length_c                   22.7579(8)
_cell_angle_alpha                90.00
_cell_angle_beta                 128.0360(10)
_cell_angle_gamma                90.00
_cell_volume                     6382.9(4)
_cell_formula_units_Z            8
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    ?
_cell_measurement_theta_min      ?
_cell_measurement_theta_max      ?

_exptl_crystal_description       block
_exptl_crystal_colour            brown
_exptl_crystal_size_max          0.4
_exptl_crystal_size_mid          0.3
_exptl_crystal_size_min          0.2
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.287
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             2632
_exptl_absorpt_coefficient_mu    0.722
_exptl_absorpt_correction_type   none
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   ?

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      296(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  ?
_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            35516
_diffrn_reflns_av_R_equivalents  0.0912
_diffrn_reflns_av_sigmaI/netI    0.0575
_diffrn_reflns_limit_h_min       -32
_diffrn_reflns_limit_h_max       33
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_l_min       -26
_diffrn_reflns_limit_l_max       27
_diffrn_reflns_theta_min         1.83
_diffrn_reflns_theta_max         25.00
_reflns_number_total             5622
_reflns_number_gt                4006
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    ?
_computing_publication_material  ?

_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)+(0.0000P)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         5622
_refine_ls_number_parameters     388
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0596
_refine_ls_R_factor_gt           0.0410
_refine_ls_wR_factor_ref         0.0765
_refine_ls_wR_factor_gt          0.0745
_refine_ls_goodness_of_fit_ref   1.473
_refine_ls_restrained_S_all      1.473
_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 0.017907(13) 0.79452(2) 0.557223(17) 0.03770(11) Uani 1 1 d . . .
N2 N -0.02913(8) 0.87569(15) 0.58621(11) 0.0306(5) Uani 1 1 d . . .
N1 N -0.06298(9) 0.72925(16) 0.47264(11) 0.0372(5) Uani 1 1 d . . .
O2 O 0.06518(8) 0.69318(14) 0.54925(11) 0.0506(5) Uani 1 1 d . . .
O1 O 0.08368(7) 0.88925(14) 0.60793(10) 0.0453(5) Uani 1 1 d . . .
O3 O 0.06038(10) 0.78352(19) 0.46338(13) 0.0877(8) Uani 1 1 d . . .
C11 C 0.09966(11) 0.9513(2) 0.66493(15) 0.0345(6) Uani 1 1 d . . .
C5 C -0.00866(10) 0.98964(18) 0.59818(14) 0.0369(7) Uani 1 1 d . . .
H5A H -0.0139 1.0148 0.5542 0.044 Uiso 1 1 calc R . .
H5B H -0.0337 1.0327 0.6045 0.044 Uiso 1 1 calc R . .
C4 C -0.09331(11) 0.8706(2) 0.51807(15) 0.0425(7) Uani 1 1 d . . .
H4A H -0.1005 0.9229 0.4822 0.051 Uiso 1 1 calc R . .
H4B H -0.1194 0.8868 0.5312 0.051 Uiso 1 1 calc R . .
C10 C 0.16148(11) 0.9696(2) 0.72504(15) 0.0369(7) Uani 1 1 d . . .
C9 C 0.17457(11) 1.0362(2) 0.78220(15) 0.0410(7) Uani 1 1 d . . .
H9 H 0.2149 1.0485 0.8217 0.049 Uiso 1 1 calc R . .
C8 C 0.13126(12) 1.0856(2) 0.78412(15) 0.0385(7) Uani 1 1 d . . .
C7 C 0.07180(12) 1.0679(2) 0.72379(16) 0.0403(7) Uani 1 1 d . . .
H7 H 0.0417 1.1006 0.7227 0.048 Uiso 1 1 calc R . .
C3 C -0.10808(11) 0.7601(2) 0.48320(15) 0.0435(7) Uani 1 1 d . . .
H3A H -0.1077 0.7093 0.5155 0.052 Uiso 1 1 calc R . .
H3B H -0.1480 0.7601 0.4355 0.052 Uiso 1 1 calc R . .
C6 C 0.05562(11) 1.00282(19) 0.66471(14) 0.0326(6) Uani 1 1 d . . .
C2 C -0.06070(12) 0.6114(2) 0.46911(15) 0.0499(8) Uani 1 1 d . . .
H2A H -0.0488 0.5813 0.5151 0.075 Uiso 1 1 calc R . .
H2B H -0.0321 0.5920 0.4613 0.075 Uiso 1 1 calc R . .
H2C H -0.0998 0.5852 0.4286 0.075 Uiso 1 1 calc R . .
C1 C -0.07939(12) 0.7754(2) 0.40214(14) 0.0528(8) Uani 1 1 d . . .
H1A H -0.0491 0.7575 0.3969 0.079 Uiso 1 1 calc R . .
H1B H -0.0822 0.8510 0.4034 0.079 Uiso 1 1 calc R . .
H1C H -0.1175 0.7474 0.3606 0.079 Uiso 1 1 calc R . .
C12 C 0.15052(13) 1.1576(2) 0.84993(16) 0.0471(8) Uani 1 1 d . . .
C13 C 0.09639(14) 1.2033(3) 0.8414(2) 0.0846(11) Uani 1 1 d . . .
H13A H 0.0732 1.2465 0.7974 0.127 Uiso 1 1 calc R . .
H13B H 0.1102 1.2455 0.8843 0.127 Uiso 1 1 calc R . .
H13C H 0.0718 1.1465 0.8371 0.127 Uiso 1 1 calc R . .
C14 C 0.18677(14) 1.2521(2) 0.85370(18) 0.0741(10) Uani 1 1 d . . .
H14A H 0.2217 1.2265 0.8601 0.111 Uiso 1 1 calc R . .
H14B H 0.1990 1.2966 0.8951 0.111 Uiso 1 1 calc R . .
H14C H 0.1622 1.2921 0.8083 0.111 Uiso 1 1 calc R . .
C18 C 0.20678(12) 0.7970(2) 0.72550(16) 0.0562(8) Uani 1 1 d . . .
H18A H 0.1683 0.7742 0.6816 0.084 Uiso 1 1 calc R . .
H18B H 0.2112 0.7754 0.7691 0.084 Uiso 1 1 calc R . .
H18C H 0.2381 0.7656 0.7262 0.084 Uiso 1 1 calc R . .
C16 C 0.21113(11) 0.9190(2) 0.72480(15) 0.0416(7) Uani 1 1 d . . .
C19 C 0.20458(12) 0.9536(2) 0.65572(16) 0.0590(9) Uani 1 1 d . . .
H19A H 0.1665 0.9299 0.6117 0.088 Uiso 1 1 calc R . .
H19B H 0.2365 0.9233 0.6572 0.088 Uiso 1 1 calc R . .
H19C H 0.2066 1.0294 0.6550 0.088 Uiso 1 1 calc R . .
C17 C 0.27443(11) 0.9513(2) 0.79382(17) 0.0679(10) Uani 1 1 d . . .
H17A H 0.3040 0.9198 0.7912 0.102 Uiso 1 1 calc R . .
H17B H 0.2806 0.9273 0.8381 0.102 Uiso 1 1 calc R . .
H17C H 0.2782 1.0270 0.7953 0.102 Uiso 1 1 calc R . .
C22 C -0.09796(11) 0.7121(2) 0.63815(14) 0.0380(7) Uani 1 1 d . . .
C34 C -0.00421(12) 0.6467(2) 0.66620(13) 0.0365(7) Uani 1 1 d . . .
C20 C -0.02185(11) 0.8427(2) 0.65515(14) 0.0367(7) Uani 1 1 d . . .
H20A H 0.0202 0.8500 0.6980 0.044 Uiso 1 1 calc R . .
H20B H -0.0447 0.8912 0.6621 0.044 Uiso 1 1 calc R . .
C29 C -0.02452(13) 0.5398(2) 0.65887(14) 0.0428(7) Uani 1 1 d . . .
C23 C -0.13715(12) 0.7931(2) 0.62972(16) 0.0526(8) Uani 1 1 d . . .
H23 H -0.1249 0.8634 0.6371 0.063 Uiso 1 1 calc R . .
C21 C -0.04158(11) 0.7312(2) 0.65406(13) 0.0347(6) Uani 1 1 d . . .
C33 C 0.05442(12) 0.6611(2) 0.68600(14) 0.0439(7) Uani 1 1 d . . .
H33 H 0.0692 0.7294 0.6920 0.053 Uiso 1 1 calc R . .
C27 C -0.11826(13) 0.6046(2) 0.62933(15) 0.0450(7) Uani 1 1 d . . .
C28 C -0.08113(14) 0.5229(2) 0.63941(15) 0.0516(8) Uani 1 1 d . . .
H28 H -0.0948 0.4536 0.6328 0.062 Uiso 1 1 calc R . .
C32 C 0.08886(14) 0.5773(3) 0.69618(16) 0.0591(9) Uani 1 1 d . . .
H32 H 0.1265 0.5889 0.7082 0.071 Uiso 1 1 calc R . .
C26 C -0.17626(14) 0.5850(3) 0.60971(17) 0.0648(9) Uani 1 1 d . . .
H26 H -0.1896 0.5155 0.6032 0.078 Uiso 1 1 calc R . .
C31 C 0.06821(16) 0.4731(3) 0.68870(17) 0.0658(10) Uani 1 1 d . . .
H31 H 0.0924 0.4164 0.6962 0.079 Uiso 1 1 calc R . .
C30 C 0.01372(16) 0.4547(2) 0.67082(16) 0.0594(9) Uani 1 1 d . . .
H30 H 0.0008 0.3853 0.6662 0.071 Uiso 1 1 calc R . .
C25 C -0.21180(15) 0.6641(3) 0.60044(19) 0.0754(11) Uani 1 1 d . . .
H25 H -0.2497 0.6494 0.5869 0.091 Uiso 1 1 calc R . .
C24 C -0.19194(14) 0.7696(3) 0.61113(18) 0.0686(10) Uani 1 1 d . . .
H24 H -0.2167 0.8241 0.6054 0.082 Uiso 1 1 calc R . .
C15 C 0.18992(17) 1.0962(3) 0.92325(18) 0.0989(14) Uani 1 1 d . . .
H15A H 0.1666 1.0411 0.9235 0.148 Uiso 1 1 calc R . .
H15B H 0.2047 1.1435 0.9642 0.148 Uiso 1 1 calc R . .
H15C H 0.2233 1.0653 0.9281 0.148 Uiso 1 1 calc R . .
C35 C 0.08137(13) 0.7160(2) 0.51144(17) 0.0453(7) Uani 1 1 d . . .
C36 C 0.13584(12) 0.6516(3) 0.53016(18) 0.0689(10) Uani 1 1 d . . .
H36A H 0.1551 0.6898 0.5137 0.103 Uiso 1 1 calc R . .
H36B H 0.1222 0.5843 0.5053 0.103 Uiso 1 1 calc R . .
H36C H 0.1640 0.6407 0.5831 0.103 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 1.8882(17) . ?
Cu1 O2 1.9355(18) . ?
Cu1 N1 2.044(2) . ?
Cu1 N2 2.0795(19) . ?
N2 C4 1.492(3) . ?
N2 C20 1.510(3) . ?
N2 C5 1.511(3) . ?
N1 C3 1.485(3) . ?
N1 C1 1.487(3) . ?
N1 C2 1.494(3) . ?
O2 C35 1.231(3) . ?
O1 C11 1.334(3) . ?
O3 C35 1.214(3) . ?
C11 C6 1.399(3) . ?
C11 C10 1.423(3) . ?
C5 C6 1.491(3) . ?
C4 C3 1.531(3) . ?
C10 C9 1.394(4) . ?
C10 C16 1.543(3) . ?
C9 C8 1.396(3) . ?
C8 C7 1.382(3) . ?
C8 C12 1.537(4) . ?
C7 C6 1.391(3) . ?
C12 C15 1.528(4) . ?
C12 C13 1.529(4) . ?
C12 C14 1.539(4) . ?
C18 C16 1.546(4) . ?
C16 C19 1.529(4) . ?
C16 C17 1.538(3) . ?
C22 C21 1.417(3) . ?
C22 C23 1.429(3) . ?
C22 C27 1.439(3) . ?
C34 C21 1.403(3) . ?
C34 C33 1.432(3) . ?
C34 C29 1.434(4) . ?
C20 C21 1.508(3) . ?
C29 C28 1.386(4) . ?
C29 C30 1.425(4) . ?
C23 C24 1.360(4) . ?
C33 C32 1.356(4) . ?
C27 C28 1.385(4) . ?
C27 C26 1.427(4) . ?
C32 C31 1.406(4) . ?
C26 C25 1.337(4) . ?
C31 C30 1.346(4) . ?
C25 C24 1.406(4) . ?
C35 C36 1.548(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
O1 Cu1 O2 90.11(7) . . ?
O1 Cu1 N1 159.58(8) . . ?
O2 Cu1 N1 94.52(8) . . ?
O1 Cu1 N2 94.15(7) . . ?
O2 Cu1 N2 165.15(8) . . ?
N1 Cu1 N2 86.41(8) . . ?
C4 N2 C20 111.67(18) . . ?
C4 N2 C5 108.20(18) . . ?
C20 N2 C5 106.45(19) . . ?
C4 N2 Cu1 104.57(14) . . ?
C20 N2 Cu1 119.26(15) . . ?
C5 N2 Cu1 106.19(14) . . ?
C3 N1 C1 110.1(2) . . ?
C3 N1 C2 109.9(2) . . ?
C1 N1 C2 109.1(2) . . ?
C3 N1 Cu1 108.20(15) . . ?
C1 N1 Cu1 106.43(15) . . ?
C2 N1 Cu1 113.09(15) . . ?
C35 O2 Cu1 119.0(2) . . ?
C11 O1 Cu1 125.64(16) . . ?
O1 C11 C6 120.1(2) . . ?
O1 C11 C10 120.7(2) . . ?
C6 C11 C10 119.2(2) . . ?
C6 C5 N2 112.32(19) . . ?
N2 C4 C3 110.3(2) . . ?
C9 C10 C11 117.3(2) . . ?
C9 C10 C16 122.3(2) . . ?
C11 C10 C16 120.4(2) . . ?
C10 C9 C8 124.4(2) . . ?
C7 C8 C9 116.5(2) . . ?
C7 C8 C12 123.2(2) . . ?
C9 C8 C12 120.3(2) . . ?
C8 C7 C6 122.0(2) . . ?
N1 C3 C4 109.7(2) . . ?
C7 C6 C11 120.6(2) . . ?
C7 C6 C5 121.1(2) . . ?
C11 C6 C5 118.2(2) . . ?
C15 C12 C13 109.1(3) . . ?
C15 C12 C8 110.3(2) . . ?
C13 C12 C8 112.0(2) . . ?
C15 C12 C14 108.7(2) . . ?
C13 C12 C14 106.9(2) . . ?
C8 C12 C14 109.7(2) . . ?
C19 C16 C17 107.6(2) . . ?
C19 C16 C10 110.5(2) . . ?
C17 C16 C10 111.8(2) . . ?
C19 C16 C18 109.6(2) . . ?
C17 C16 C18 107.7(2) . . ?
C10 C16 C18 109.6(2) . . ?
C21 C22 C23 124.5(2) . . ?
C21 C22 C27 118.9(3) . . ?
C23 C22 C27 116.6(2) . . ?
C21 C34 C33 123.1(3) . . ?
C21 C34 C29 119.7(2) . . ?
C33 C34 C29 117.2(3) . . ?
C21 C20 N2 115.3(2) . . ?
C28 C29 C30 122.2(3) . . ?
C28 C29 C34 118.8(3) . . ?
C30 C29 C34 119.1(3) . . ?
C24 C23 C22 121.5(3) . . ?
C34 C21 C22 120.6(2) . . ?
C34 C21 C20 118.8(2) . . ?
C22 C21 C20 120.5(2) . . ?
C32 C33 C34 121.4(3) . . ?
C28 C27 C26 121.8(3) . . ?
C28 C27 C22 119.0(3) . . ?
C26 C27 C22 119.2(3) . . ?
C27 C28 C29 122.9(3) . . ?
C33 C32 C31 120.7(3) . . ?
C25 C26 C27 121.5(3) . . ?
C30 C31 C32 120.6(3) . . ?
C31 C30 C29 121.1(3) . . ?
C26 C25 C24 120.0(3) . . ?
C23 C24 C25 121.0(3) . . ?
O3 C35 O2 127.5(3) . . ?
O3 C35 C36 117.8(3) . . ?
O2 C35 C36 114.6(3) . . ?

_diffrn_measured_fraction_theta_max 1.000
_diffrn_reflns_theta_full        25.00
_diffrn_measured_fraction_theta_full 1.000
_refine_diff_density_max         0.370
_refine_diff_density_min         -0.409
_refine_diff_density_rms         0.070

_database_code_depnum_ccdc_archive 'CCDC 1013006'
