# 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_shelxl
#TrackingRef 'RKPM1.cif'


_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C21 H19 N3 O'
_chemical_formula_sum            'C21 H19 N3 O'
_chemical_formula_weight         329.39

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           monoclinic
_symmetry_space_group_name_H-M   'P 21/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                   13.1445(8)
_cell_length_b                   8.7158(5)
_cell_length_c                   15.1599(11)
_cell_angle_alpha                90.00
_cell_angle_beta                 99.094(6)
_cell_angle_gamma                90.00
_cell_volume                     1714.96(19)
_cell_formula_units_Z            4
_cell_measurement_temperature    298(2)
_cell_measurement_reflns_used    2709
_cell_measurement_theta_min      3.0
_cell_measurement_theta_max      25.0

_exptl_crystal_description       ?
_exptl_crystal_colour            ?
_exptl_crystal_size_max          0.12
_exptl_crystal_size_mid          0.10
_exptl_crystal_size_min          0.08
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.276
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             696
_exptl_absorpt_coefficient_mu    0.080
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.9904
_exptl_absorpt_correction_T_max  0.9936
_exptl_absorpt_process_details   sadabs

_exptl_special_details           
;
?
;

_diffrn_ambient_temperature      298(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            13105
_diffrn_reflns_av_R_equivalents  0.0218
_diffrn_reflns_av_sigmaI/netI    0.0225
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_theta_min         2.92
_diffrn_reflns_theta_max         25.99
_reflns_number_total             3372
_reflns_number_gt                2709
_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)+(0.0509P)²+0.2864P] 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         3372
_refine_ls_number_parameters     231
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0591
_refine_ls_R_factor_gt           0.0455
_refine_ls_wR_factor_ref         0.1134
_refine_ls_wR_factor_gt          0.1067
_refine_ls_goodness_of_fit_ref   1.036
_refine_ls_restrained_S_all      1.036
_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
C1 C -0.00211(12) 0.33178(17) 0.13651(10) 0.0446(4) Uani 1 1 d . . .
C2 C -0.04067(13) 0.18757(18) 0.15241(11) 0.0560(4) Uani 1 1 d . . .
H2 H -0.0016 0.0996 0.1484 0.067 Uiso 1 1 calc R . .
C3 C -0.13816(15) 0.1787(2) 0.17422(12) 0.0634(5) Uani 1 1 d . . .
H3 H -0.1656 0.0832 0.1846 0.076 Uiso 1 1 calc R . .
C4 C -0.19634(14) 0.3098(2) 0.18100(12) 0.0643(5) Uani 1 1 d . . .
H4 H -0.2615 0.3000 0.1970 0.077 Uiso 1 1 calc R . .
C5 C -0.16072(12) 0.4541(2) 0.16485(11) 0.0556(4) Uani 1 1 d . . .
H5 H -0.2002 0.5415 0.1692 0.067 Uiso 1 1 calc R . .
C6 C -0.06299(11) 0.46217(17) 0.14183(10) 0.0440(4) Uani 1 1 d . . .
C7 C -0.03425(14) 0.74469(18) 0.11564(12) 0.0595(5) Uani 1 1 d . . .
H7A H 0.0212 0.8070 0.1450 0.089 Uiso 1 1 calc R . .
H7B H -0.0939 0.7589 0.1440 0.089 Uiso 1 1 calc R . .
H7C H -0.0502 0.7741 0.0540 0.089 Uiso 1 1 calc R . .
C8 C 0.08804(11) 0.52392(17) 0.10699(10) 0.0437(4) Uani 1 1 d . . .
C9 C 0.17426(12) 0.62017(19) 0.08609(11) 0.0520(4) Uani 1 1 d . . .
H9A H 0.1859 0.7041 0.1285 0.062 Uiso 1 1 calc R . .
H9B H 0.1557 0.6638 0.0269 0.062 Uiso 1 1 calc R . .
C10 C 0.27247(13) 0.5285(2) 0.08977(11) 0.0569(4) Uani 1 1 d . . .
H10A H 0.2604 0.4431 0.0484 0.068 Uiso 1 1 calc R . .
H10B H 0.3253 0.5929 0.0711 0.068 Uiso 1 1 calc R . .
C11 C 0.40054(11) 0.49008(18) 0.22420(11) 0.0478(4) Uani 1 1 d . . .
H11 H 0.4461 0.5519 0.1991 0.057 Uiso 1 1 calc R . .
C12 C 0.43558(11) 0.42472(16) 0.30814(10) 0.0435(4) Uani 1 1 d . . .
C13 C 0.36625(12) 0.32850(17) 0.34743(11) 0.0479(4) Uani 1 1 d . . .
C14 C 0.40575(14) 0.2553(2) 0.43076(12) 0.0601(5) Uani 1 1 d . . .
H14 H 0.3635 0.1882 0.4561 0.072 Uiso 1 1 calc R . .
C15 C 0.50135(15) 0.2810(2) 0.47277(12) 0.0625(5) Uani 1 1 d . . .
H15 H 0.5231 0.2321 0.5270 0.075 Uiso 1 1 calc R . .
C16 C 0.57132(12) 0.38008(18) 0.43787(11) 0.0509(4) Uani 1 1 d . . .
C17 C 0.67013(14) 0.4076(2) 0.48436(13) 0.0651(5) Uani 1 1 d . . .
H17 H 0.6900 0.3615 0.5397 0.078 Uiso 1 1 calc R . .
C18 C 0.73811(14) 0.5001(2) 0.45086(14) 0.0681(5) Uani 1 1 d . . .
H18 H 0.8034 0.5174 0.4830 0.082 Uiso 1 1 calc R . .
C19 C 0.70886(13) 0.5681(2) 0.36829(14) 0.0657(5) Uani 1 1 d . . .
H19 H 0.7552 0.6303 0.3444 0.079 Uiso 1 1 calc R . .
C20 C 0.61200(12) 0.54445(19) 0.32145(12) 0.0579(4) Uani 1 1 d . . .
H20 H 0.5938 0.5918 0.2662 0.069 Uiso 1 1 calc R . .
C21 C 0.53955(11) 0.45101(16) 0.35423(10) 0.0444(4) Uani 1 1 d . . .
N1 N -0.00363(9) 0.58394(14) 0.12168(8) 0.0449(3) Uani 1 1 d . . .
N2 N 0.09260(9) 0.37358(14) 0.11489(8) 0.0473(3) Uani 1 1 d . . .
N3 N 0.30862(10) 0.47019(16) 0.17897(9) 0.0512(3) Uani 1 1 d . . .
O1 O 0.27354(8) 0.30557(14) 0.31143(8) 0.0606(3) Uani 1 1 d . . .
H3A H 0.2683(14) 0.411(2) 0.2042(12) 0.069(6) Uiso 1 1 d . . .


_geom_special_details            
;
All esds (except the esd in the dihedral angle between two l.s. planes)
are estimated using the full covariance matrix. The cell esds are taken
into account individually in the estimation of esds in distances, angles
and torsion angles; correlations between esds in cell parameters are only
used when they are defined by crystal symmetry. An approximate (isotropic)
treatment of cell esds is used for estimating esds involving l.s. planes.
;

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
C1 N2 1.385(2) . ?
C1 C2 1.391(2) . ?
C1 C6 1.400(2) . ?
C2 C3 1.375(2) . ?
C2 H2 0.9300 . ?
C3 C4 1.388(3) . ?
C3 H3 0.9300 . ?
C4 C5 1.377(2) . ?
C4 H4 0.9300 . ?
C5 C6 1.385(2) . ?
C5 H5 0.9300 . ?
C6 N1 1.380(2) . ?
C7 N1 1.4566(19) . ?
C7 H7A 0.9600 . ?
C7 H7B 0.9600 . ?
C7 H7C 0.9600 . ?
C8 N2 1.3163(19) . ?
C8 N1 1.3639(19) . ?
C8 C9 1.484(2) . ?
C9 C10 1.512(2) . ?
C9 H9A 0.9700 . ?
C9 H9B 0.9700 . ?
C10 N3 1.452(2) . ?
C10 H10A 0.9700 . ?
C10 H10B 0.9700 . ?
C11 N3 1.3032(19) . ?
C11 C12 1.404(2) . ?
C11 H11 0.9300 . ?
C12 C13 1.435(2) . ?
C12 C21 1.451(2) . ?
C13 O1 1.2699(18) . ?
C13 C14 1.437(2) . ?
C14 C15 1.335(2) . ?
C14 H14 0.9300 . ?
C15 C16 1.423(2) . ?
C15 H15 0.9300 . ?
C16 C17 1.397(2) . ?
C16 C21 1.413(2) . ?
C17 C18 1.360(3) . ?
C17 H17 0.9300 . ?
C18 C19 1.384(3) . ?
C18 H18 0.9300 . ?
C19 C20 1.372(2) . ?
C19 H19 0.9300 . ?
C20 C21 1.402(2) . ?
C20 H20 0.9300 . ?
N3 H3A 0.868(19) . ?

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
N2 C1 C2 130.13(14) . . ?
N2 C1 C6 110.09(13) . . ?
C2 C1 C6 119.78(15) . . ?
C3 C2 C1 118.14(16) . . ?
C3 C2 H2 120.9 . . ?
C1 C2 H2 120.9 . . ?
C2 C3 C4 121.11(17) . . ?
C2 C3 H3 119.4 . . ?
C4 C3 H3 119.4 . . ?
C5 C4 C3 122.13(17) . . ?
C5 C4 H4 118.9 . . ?
C3 C4 H4 118.9 . . ?
C4 C5 C6 116.50(16) . . ?
C4 C5 H5 121.7 . . ?
C6 C5 H5 121.7 . . ?
N1 C6 C5 132.41(14) . . ?
N1 C6 C1 105.27(13) . . ?
C5 C6 C1 122.32(15) . . ?
N1 C7 H7A 109.5 . . ?
N1 C7 H7B 109.5 . . ?
H7A C7 H7B 109.5 . . ?
N1 C7 H7C 109.5 . . ?
H7A C7 H7C 109.5 . . ?
H7B C7 H7C 109.5 . . ?
N2 C8 N1 113.31(13) . . ?
N2 C8 C9 123.84(14) . . ?
N1 C8 C9 122.84(13) . . ?
C8 C9 C10 111.70(14) . . ?
C8 C9 H9A 109.3 . . ?
C10 C9 H9A 109.3 . . ?
C8 C9 H9B 109.3 . . ?
C10 C9 H9B 109.3 . . ?
H9A C9 H9B 107.9 . . ?
N3 C10 C9 111.78(13) . . ?
N3 C10 H10A 109.3 . . ?
C9 C10 H10A 109.3 . . ?
N3 C10 H10B 109.3 . . ?
C9 C10 H10B 109.3 . . ?
H10A C10 H10B 107.9 . . ?
N3 C11 C12 124.54(14) . . ?
N3 C11 H11 117.7 . . ?
C12 C11 H11 117.7 . . ?
C11 C12 C13 118.32(14) . . ?
C11 C12 C21 121.42(13) . . ?
C13 C12 C21 120.25(14) . . ?
O1 C13 C12 122.87(15) . . ?
O1 C13 C14 119.79(14) . . ?
C12 C13 C14 117.34(14) . . ?
C15 C14 C13 121.82(15) . . ?
C15 C14 H14 119.1 . . ?
C13 C14 H14 119.1 . . ?
C14 C15 C16 122.63(16) . . ?
C14 C15 H15 118.7 . . ?
C16 C15 H15 118.7 . . ?
C17 C16 C21 119.78(16) . . ?
C17 C16 C15 121.38(16) . . ?
C21 C16 C15 118.84(15) . . ?
C18 C17 C16 121.79(18) . . ?
C18 C17 H17 119.1 . . ?
C16 C17 H17 119.1 . . ?
C17 C18 C19 119.13(17) . . ?
C17 C18 H18 120.4 . . ?
C19 C18 H18 120.4 . . ?
C20 C19 C18 120.43(17) . . ?
C20 C19 H19 119.8 . . ?
C18 C19 H19 119.8 . . ?
C19 C20 C21 122.04(17) . . ?
C19 C20 H20 119.0 . . ?
C21 C20 H20 119.0 . . ?
C20 C21 C16 116.82(14) . . ?
C20 C21 C12 124.17(14) . . ?
C16 C21 C12 119.02(14) . . ?
C8 N1 C6 106.63(12) . . ?
C8 N1 C7 126.95(14) . . ?
C6 N1 C7 126.40(13) . . ?
C8 N2 C1 104.70(12) . . ?
C11 N3 C10 125.66(15) . . ?
C11 N3 H3A 115.2(12) . . ?
C10 N3 H3A 118.9(12) . . ?

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
N2 C1 C2 C3 179.03(15) . . . . ?
C6 C1 C2 C3 -0.8(2) . . . . ?
C1 C2 C3 C4 -0.6(3) . . . . ?
C2 C3 C4 C5 1.2(3) . . . . ?
C3 C4 C5 C6 -0.4(2) . . . . ?
C4 C5 C6 N1 -179.81(15) . . . . ?
C4 C5 C6 C1 -1.1(2) . . . . ?
N2 C1 C6 N1 0.85(16) . . . . ?
C2 C1 C6 N1 -179.27(13) . . . . ?
N2 C1 C6 C5 -178.20(13) . . . . ?
C2 C1 C6 C5 1.7(2) . . . . ?
N2 C8 C9 C10 -9.2(2) . . . . ?
N1 C8 C9 C10 169.49(13) . . . . ?
C8 C9 C10 N3 -63.49(18) . . . . ?
N3 C11 C12 C13 0.3(2) . . . . ?
N3 C11 C12 C21 179.44(14) . . . . ?
C11 C12 C13 O1 -3.2(2) . . . . ?
C21 C12 C13 O1 177.68(14) . . . . ?
C11 C12 C13 C14 176.27(14) . . . . ?
C21 C12 C13 C14 -2.9(2) . . . . ?
O1 C13 C14 C15 -177.26(16) . . . . ?
C12 C13 C14 C15 3.3(2) . . . . ?
C13 C14 C15 C16 -0.9(3) . . . . ?
C14 C15 C16 C17 178.45(17) . . . . ?
C14 C15 C16 C21 -1.8(3) . . . . ?
C21 C16 C17 C18 -0.8(3) . . . . ?
C15 C16 C17 C18 178.88(17) . . . . ?
C16 C17 C18 C19 -0.4(3) . . . . ?
C17 C18 C19 C20 1.0(3) . . . . ?
C18 C19 C20 C21 -0.4(3) . . . . ?
C19 C20 C21 C16 -0.8(2) . . . . ?
C19 C20 C21 C12 178.75(16) . . . . ?
C17 C16 C21 C20 1.4(2) . . . . ?
C15 C16 C21 C20 -178.35(15) . . . . ?
C17 C16 C21 C12 -178.17(14) . . . . ?
C15 C16 C21 C12 2.1(2) . . . . ?
C11 C12 C21 C20 1.6(2) . . . . ?
C13 C12 C21 C20 -179.25(15) . . . . ?
C11 C12 C21 C16 -178.86(14) . . . . ?
C13 C12 C21 C16 0.3(2) . . . . ?
N2 C8 N1 C6 0.74(16) . . . . ?
C9 C8 N1 C6 -178.05(13) . . . . ?
N2 C8 N1 C7 -178.13(14) . . . . ?
C9 C8 N1 C7 3.1(2) . . . . ?
C5 C6 N1 C8 177.98(16) . . . . ?
C1 C6 N1 C8 -0.93(15) . . . . ?
C5 C6 N1 C7 -3.1(3) . . . . ?
C1 C6 N1 C7 177.95(14) . . . . ?
N1 C8 N2 C1 -0.21(16) . . . . ?
C9 C8 N2 C1 178.57(13) . . . . ?
C2 C1 N2 C8 179.72(16) . . . . ?
C6 C1 N2 C8 -0.41(16) . . . . ?
C12 C11 N3 C10 -175.93(15) . . . . ?
C9 C10 N3 C11 -126.44(17) . . . . ?

_diffrn_measured_fraction_theta_max 0.999
_diffrn_reflns_theta_full        25.99
_diffrn_measured_fraction_theta_full 0.999
_refine_diff_density_max         0.183
_refine_diff_density_min         -0.159
_refine_diff_density_rms         0.029
_database_code_depnum_ccdc_archive 'CCDC 932002'
#######################################################################
#
#                 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_shelxl4
#TrackingRef 'RKPM4.cif'


_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C21 H18 Cu N4 O4'
_chemical_formula_sum            'C21 H18 Cu N4 O4'
_chemical_formula_weight         453.93

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           triclinic
_symmetry_space_group_name_H-M   'P -1'
_symmetry_space_group_name_Hall  '-P 1'
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   8.1881(4)
_cell_length_b                   14.3725(7)
_cell_length_c                   16.7302(8)
_cell_angle_alpha                69.370(4)
_cell_angle_beta                 83.087(4)
_cell_angle_gamma                87.734(4)
_cell_volume                     1829.21(15)
_cell_formula_units_Z            4
_cell_measurement_temperature    150(2)
_cell_measurement_reflns_used    6396
_cell_measurement_theta_min      3.0
_cell_measurement_theta_max      26.0

_exptl_crystal_description       ?
_exptl_crystal_colour            ?
_exptl_crystal_size_max          0.12
_exptl_crystal_size_mid          0.11
_exptl_crystal_size_min          0.10
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.648
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             932
_exptl_absorpt_coefficient_mu    1.234
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.8661
_exptl_absorpt_correction_T_max  0.8866
_exptl_absorpt_process_details   sadabs

_exptl_special_details           
;
?
;

_diffrn_ambient_temperature      150(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            24033
_diffrn_reflns_av_R_equivalents  0.0273
_diffrn_reflns_av_sigmaI/netI    0.0295
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_theta_min         2.92
_diffrn_reflns_theta_max         26.00
_reflns_number_total             7164
_reflns_number_gt                6396
_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)+(0.0331P)²+1.3764P] 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         7164
_refine_ls_number_parameters     543
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0355
_refine_ls_R_factor_gt           0.0304
_refine_ls_wR_factor_ref         0.0767
_refine_ls_wR_factor_gt          0.0745
_refine_ls_goodness_of_fit_ref   1.038
_refine_ls_restrained_S_all      1.038
_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
C1 C 0.1244(2) 0.12588(15) 0.42351(13) 0.0169(4) Uani 1 1 d . . .
C2 C 0.0266(3) 0.20898(15) 0.38401(13) 0.0203(4) Uani 1 1 d . . .
H2 H -0.0360 0.2406 0.4187 0.024 Uiso 1 1 calc R . .
C3 C 0.0199(3) 0.24517(16) 0.29665(14) 0.0234(5) Uani 1 1 d . . .
H3 H -0.0464 0.3014 0.2720 0.028 Uiso 1 1 calc R . .
C4 C 0.1097(3) 0.20011(17) 0.24352(14) 0.0266(5) Uani 1 1 d . . .
H4 H 0.1054 0.2257 0.1831 0.032 Uiso 1 1 calc R . .
C5 C 0.2039(3) 0.11849(17) 0.28002(14) 0.0258(5) Uani 1 1 d . . .
H5 H 0.2641 0.0872 0.2443 0.031 Uiso 1 1 calc R . .
C6 C 0.2132(3) 0.08002(15) 0.36930(13) 0.0198(4) Uani 1 1 d . . .
C7 C 0.3124(3) -0.00485(16) 0.40632(14) 0.0233(5) Uani 1 1 d . . .
H7 H 0.3732 -0.0349 0.3699 0.028 Uiso 1 1 calc R . .
C8 C 0.3218(3) -0.04346(16) 0.49200(14) 0.0214(5) Uani 1 1 d . . .
H8 H 0.3874 -0.1008 0.5144 0.026 Uiso 1 1 calc R . .
C9 C 0.2348(3) 0.00034(15) 0.54992(13) 0.0185(4) Uani 1 1 d . . .
C10 C 0.1387(2) 0.08591(15) 0.51511(13) 0.0165(4) Uani 1 1 d . . .
C11 C 0.0659(2) 0.13848(15) 0.56876(13) 0.0177(4) Uani 1 1 d . . .
H11 H 0.0118 0.1989 0.5408 0.021 Uiso 1 1 calc R . .
C12 C 0.0019(3) 0.18557(15) 0.69088(13) 0.0215(5) Uani 1 1 d . . .
H12A H -0.0318 0.2466 0.6457 0.026 Uiso 1 1 calc R . .
H12B H 0.0912 0.2038 0.7176 0.026 Uiso 1 1 calc R . .
C13 C -0.1432(3) 0.14592(15) 0.75853(13) 0.0214(5) Uani 1 1 d . . .
H13A H -0.1825 0.1986 0.7815 0.026 Uiso 1 1 calc R . .
H13B H -0.2337 0.1303 0.7310 0.026 Uiso 1 1 calc R . .
C14 C -0.1053(2) 0.05521(15) 0.83159(13) 0.0165(4) Uani 1 1 d . . .
C15 C -0.3265(3) 0.09051(16) 0.93373(14) 0.0229(5) Uani 1 1 d . . .
H15A H -0.2877 0.1580 0.9228 0.034 Uiso 1 1 calc R . .
H15B H -0.3649 0.0589 0.9950 0.034 Uiso 1 1 calc R . .
H15C H -0.4173 0.0936 0.8997 0.034 Uiso 1 1 calc R . .
C16 C -0.1338(2) -0.05723(15) 0.96219(13) 0.0171(4) Uani 1 1 d . . .
C17 C -0.1786(3) -0.11294(16) 1.04826(13) 0.0216(5) Uani 1 1 d . . .
H17 H -0.2611 -0.0911 1.0826 0.026 Uiso 1 1 calc R . .
C18 C -0.0970(3) -0.20161(16) 1.08105(14) 0.0250(5) Uani 1 1 d . . .
H18 H -0.1239 -0.2420 1.1396 0.030 Uiso 1 1 calc R . .
C19 C 0.0242(3) -0.23346(16) 1.03035(14) 0.0246(5) Uani 1 1 d . . .
H19 H 0.0758 -0.2958 1.0550 0.029 Uiso 1 1 calc R . .
C20 C 0.0713(3) -0.17692(16) 0.94543(14) 0.0216(5) Uani 1 1 d . . .
H20 H 0.1550 -0.1988 0.9117 0.026 Uiso 1 1 calc R . .
C21 C -0.0090(2) -0.08617(15) 0.91103(13) 0.0172(4) Uani 1 1 d . . .
C22 C 0.5041(2) 0.41549(15) 0.63506(13) 0.0177(4) Uani 1 1 d . . .
C23 C 0.4422(3) 0.31911(16) 0.66153(13) 0.0210(5) Uani 1 1 d . . .
H23 H 0.3557 0.2963 0.7071 0.025 Uiso 1 1 calc R . .
C24 C 0.5118(3) 0.25779(16) 0.61876(14) 0.0234(5) Uani 1 1 d . . .
H24 H 0.4717 0.1918 0.6352 0.028 Uiso 1 1 calc R . .
C25 C 0.6396(3) 0.29085(17) 0.55196(14) 0.0245(5) Uani 1 1 d . . .
H25 H 0.6832 0.2470 0.5236 0.029 Uiso 1 1 calc R . .
C26 C 0.7042(3) 0.38544(16) 0.52612(14) 0.0221(5) Uani 1 1 d . . .
H26 H 0.7914 0.4078 0.4809 0.027 Uiso 1 1 calc R . .
C27 C 0.6348(2) 0.44643(15) 0.56984(13) 0.0177(4) Uani 1 1 d . . .
C28 C 0.8096(3) 0.60197(17) 0.50742(14) 0.0256(5) Uani 1 1 d . . .
H28A H 0.7691 0.6671 0.4730 0.038 Uiso 1 1 calc R . .
H28B H 0.8618 0.5684 0.4692 0.038 Uiso 1 1 calc R . .
H28C H 0.8903 0.6108 0.5430 0.038 Uiso 1 1 calc R . .
C29 C 0.5693(2) 0.56640(15) 0.62170(13) 0.0178(4) Uani 1 1 d . . .
C30 C 0.5836(3) 0.66288(16) 0.63554(14) 0.0230(5) Uani 1 1 d . . .
H30A H 0.6137 0.7155 0.5791 0.028 Uiso 1 1 calc R . .
H30B H 0.6745 0.6575 0.6709 0.028 Uiso 1 1 calc R . .
C31 C 0.4287(3) 0.69502(15) 0.67909(13) 0.0228(5) Uani 1 1 d . . .
H31A H 0.4503 0.7584 0.6868 0.027 Uiso 1 1 calc R . .
H31B H 0.3394 0.7065 0.6418 0.027 Uiso 1 1 calc R . .
C32 C 0.3790(2) 0.64127(15) 0.83174(13) 0.0182(4) Uani 1 1 d . . .
H32 H 0.4206 0.7049 0.8245 0.022 Uiso 1 1 calc R . .
C33 C 0.3254(2) 0.57786(15) 0.91738(13) 0.0172(4) Uani 1 1 d . . .
C34 C 0.2289(3) 0.49268(15) 0.93305(13) 0.0187(4) Uani 1 1 d . . .
C35 C 0.1643(3) 0.43717(16) 1.01979(14) 0.0233(5) Uani 1 1 d . . .
H35 H 0.0975 0.3804 1.0308 0.028 Uiso 1 1 calc R . .
C36 C 0.1963(3) 0.46379(16) 1.08620(14) 0.0249(5) Uani 1 1 d . . .
H36 H 0.1498 0.4259 1.1427 0.030 Uiso 1 1 calc R . .
C37 C 0.2975(3) 0.54676(16) 1.07385(14) 0.0226(5) Uani 1 1 d . . .
C38 C 0.3332(3) 0.57235(17) 1.14368(15) 0.0276(5) Uani 1 1 d . . .
H38 H 0.2869 0.5342 1.2002 0.033 Uiso 1 1 calc R . .
C39 C 0.4332(3) 0.65107(18) 1.13175(15) 0.0311(6) Uani 1 1 d . . .
H39 H 0.4552 0.6679 1.1795 0.037 Uiso 1 1 calc R . .
C40 C 0.5029(3) 0.70663(18) 1.04884(15) 0.0280(5) Uani 1 1 d . . .
H40 H 0.5745 0.7605 1.0405 0.034 Uiso 1 1 calc R . .
C41 C 0.4688(3) 0.68407(16) 0.97932(15) 0.0238(5) Uani 1 1 d . . .
H41 H 0.5172 0.7230 0.9235 0.029 Uiso 1 1 calc R . .
C42 C 0.3641(3) 0.60472(15) 0.98887(13) 0.0194(4) Uani 1 1 d . . .
N1 N -0.1919(2) 0.03249(12) 0.90950(11) 0.0168(4) Uani 1 1 d . . .
N2 N 0.0075(2) -0.01324(12) 0.82846(11) 0.0178(4) Uani 1 1 d . . .
N3 N 0.0653(2) 0.11308(12) 0.65083(11) 0.0183(4) Uani 1 1 d . . .
N4 N 0.6721(2) 0.54186(13) 0.56275(11) 0.0186(4) Uani 1 1 d . . .
N5 N 0.4634(2) 0.49334(12) 0.66625(11) 0.0174(4) Uani 1 1 d . . .
N6 N 0.3760(2) 0.61967(12) 0.76299(11) 0.0187(4) Uani 1 1 d . . .
N7 N 0.4157(2) -0.03575(14) 0.81337(11) 0.0230(4) Uani 1 1 d . . .
N8 N 0.0381(2) 0.45533(13) 0.69510(11) 0.0211(4) Uani 1 1 d . . .
O1 O 0.25595(18) -0.04155(11) 0.63050(9) 0.0216(3) Uani 1 1 d . . .
O2 O 0.32961(18) -0.09516(11) 0.79306(10) 0.0237(3) Uani 1 1 d . . .
O3 O 0.5195(2) -0.07031(14) 0.86343(11) 0.0350(4) Uani 1 1 d . . .
O4 O 0.3899(2) 0.05526(12) 0.78095(11) 0.0334(4) Uani 1 1 d . . .
O5 O 0.18943(18) 0.46092(11) 0.87397(9) 0.0219(3) Uani 1 1 d . . .
O6 O 0.14491(18) 0.40117(10) 0.74051(9) 0.0213(3) Uani 1 1 d . . .
O7 O -0.0710(2) 0.41525(13) 0.67426(12) 0.0373(4) Uani 1 1 d . . .
O8 O 0.0512(2) 0.54729(11) 0.67306(11) 0.0330(4) Uani 1 1 d . . .
Cu1 Cu 0.15662(3) -0.008922(18) 0.724727(15) 0.01767(7) Uani 1 1 d . . .
Cu2 Cu 0.29771(3) 0.495390(18) 0.762436(15) 0.01713(7) Uani 1 1 d . . .


_geom_special_details            
;
All esds (except the esd in the dihedral angle between two l.s. planes)
are estimated using the full covariance matrix. The cell esds are taken
into account individually in the estimation of esds in distances, angles
and torsion angles; correlations between esds in cell parameters are only
used when they are defined by crystal symmetry. An approximate (isotropic)
treatment of cell esds is used for estimating esds involving l.s. planes.
;

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
C1 C2 1.414(3) . ?
C1 C6 1.418(3) . ?
C1 C10 1.453(3) . ?
C2 C3 1.375(3) . ?
C2 H2 0.9500 . ?
C3 C4 1.400(3) . ?
C3 H3 0.9500 . ?
C4 C5 1.371(3) . ?
C4 H4 0.9500 . ?
C5 C6 1.409(3) . ?
C5 H5 0.9500 . ?
C6 C7 1.429(3) . ?
C7 C8 1.353(3) . ?
C7 H7 0.9500 . ?
C8 C9 1.439(3) . ?
C8 H8 0.9500 . ?
C9 O1 1.298(2) . ?
C9 C10 1.414(3) . ?
C10 C11 1.430(3) . ?
C11 N3 1.290(3) . ?
C11 H11 0.9500 . ?
C12 N3 1.473(2) . ?
C12 C13 1.514(3) . ?
C12 H12A 0.9900 . ?
C12 H12B 0.9900 . ?
C13 C14 1.492(3) . ?
C13 H13A 0.9900 . ?
C13 H13B 0.9900 . ?
C14 N2 1.333(3) . ?
C14 N1 1.343(3) . ?
C15 N1 1.460(3) . ?
C15 H15A 0.9800 . ?
C15 H15B 0.9800 . ?
C15 H15C 0.9800 . ?
C16 N1 1.385(3) . ?
C16 C17 1.390(3) . ?
C16 C21 1.399(3) . ?
C17 C18 1.378(3) . ?
C17 H17 0.9500 . ?
C18 C19 1.396(3) . ?
C18 H18 0.9500 . ?
C19 C20 1.381(3) . ?
C19 H19 0.9500 . ?
C20 C21 1.400(3) . ?
C20 H20 0.9500 . ?
C21 N2 1.404(3) . ?
C22 C23 1.393(3) . ?
C22 C27 1.396(3) . ?
C22 N5 1.406(3) . ?
C23 C24 1.385(3) . ?
C23 H23 0.9500 . ?
C24 C25 1.398(3) . ?
C24 H24 0.9500 . ?
C25 C26 1.379(3) . ?
C25 H25 0.9500 . ?
C26 C27 1.392(3) . ?
C26 H26 0.9500 . ?
C27 N4 1.378(3) . ?
C28 N4 1.461(3) . ?
C28 H28A 0.9800 . ?
C28 H28B 0.9800 . ?
C28 H28C 0.9800 . ?
C29 N5 1.332(3) . ?
C29 N4 1.352(3) . ?
C29 C30 1.495(3) . ?
C30 C31 1.523(3) . ?
C30 H30A 0.9900 . ?
C30 H30B 0.9900 . ?
C31 N6 1.466(3) . ?
C31 H31A 0.9900 . ?
C31 H31B 0.9900 . ?
C32 N6 1.296(3) . ?
C32 C33 1.427(3) . ?
C32 H32 0.9500 . ?
C33 C34 1.412(3) . ?
C33 C42 1.451(3) . ?
C34 O5 1.302(3) . ?
C34 C35 1.433(3) . ?
C35 C36 1.352(3) . ?
C35 H35 0.9500 . ?
C36 C37 1.419(3) . ?
C36 H36 0.9500 . ?
C37 C38 1.407(3) . ?
C37 C42 1.424(3) . ?
C38 C39 1.366(4) . ?
C38 H38 0.9500 . ?
C39 C40 1.397(3) . ?
C39 H39 0.9500 . ?
C40 C41 1.374(3) . ?
C40 H40 0.9500 . ?
C41 C42 1.406(3) . ?
C41 H41 0.9500 . ?
N2 Cu1 1.9815(17) . ?
N3 Cu1 1.9374(17) . ?
N5 Cu2 1.9838(17) . ?
N6 Cu2 1.9247(17) . ?
N7 O3 1.231(2) . ?
N7 O4 1.247(2) . ?
N7 O2 1.285(2) . ?
N8 O7 1.228(2) . ?
N8 O8 1.246(2) . ?
N8 O6 1.280(2) . ?
O1 Cu1 1.8838(14) . ?
O2 Cu1 2.0253(15) . ?
O5 Cu2 1.8704(14) . ?
O6 Cu2 2.0318(15) . ?

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
C2 C1 C6 117.11(19) . . ?
C2 C1 C10 123.97(18) . . ?
C6 C1 C10 118.92(18) . . ?
C3 C2 C1 121.7(2) . . ?
C3 C2 H2 119.2 . . ?
C1 C2 H2 119.2 . . ?
C2 C3 C4 120.8(2) . . ?
C2 C3 H3 119.6 . . ?
C4 C3 H3 119.6 . . ?
C5 C4 C3 118.9(2) . . ?
C5 C4 H4 120.5 . . ?
C3 C4 H4 120.5 . . ?
C4 C5 C6 121.4(2) . . ?
C4 C5 H5 119.3 . . ?
C6 C5 H5 119.3 . . ?
C5 C6 C1 120.04(19) . . ?
C5 C6 C7 120.8(2) . . ?
C1 C6 C7 119.20(19) . . ?
C8 C7 C6 121.6(2) . . ?
C8 C7 H7 119.2 . . ?
C6 C7 H7 119.2 . . ?
C7 C8 C9 121.47(19) . . ?
C7 C8 H8 119.3 . . ?
C9 C8 H8 119.3 . . ?
O1 C9 C10 125.52(18) . . ?
O1 C9 C8 116.14(18) . . ?
C10 C9 C8 118.31(19) . . ?
C9 C10 C11 120.09(18) . . ?
C9 C10 C1 120.40(18) . . ?
C11 C10 C1 119.32(18) . . ?
N3 C11 C10 127.32(19) . . ?
N3 C11 H11 116.3 . . ?
C10 C11 H11 116.3 . . ?
N3 C12 C13 112.64(17) . . ?
N3 C12 H12A 109.1 . . ?
C13 C12 H12A 109.1 . . ?
N3 C12 H12B 109.1 . . ?
C13 C12 H12B 109.1 . . ?
H12A C12 H12B 107.8 . . ?
C14 C13 C12 113.85(17) . . ?
C14 C13 H13A 108.8 . . ?
C12 C13 H13A 108.8 . . ?
C14 C13 H13B 108.8 . . ?
C12 C13 H13B 108.8 . . ?
H13A C13 H13B 107.7 . . ?
N2 C14 N1 112.41(18) . . ?
N2 C14 C13 126.40(18) . . ?
N1 C14 C13 121.13(17) . . ?
N1 C15 H15A 109.5 . . ?
N1 C15 H15B 109.5 . . ?
H15A C15 H15B 109.5 . . ?
N1 C15 H15C 109.5 . . ?
H15A C15 H15C 109.5 . . ?
H15B C15 H15C 109.5 . . ?
N1 C16 C17 131.31(19) . . ?
N1 C16 C21 105.80(17) . . ?
C17 C16 C21 122.88(19) . . ?
C18 C17 C16 116.4(2) . . ?
C18 C17 H17 121.8 . . ?
C16 C17 H17 121.8 . . ?
C17 C18 C19 121.6(2) . . ?
C17 C18 H18 119.2 . . ?
C19 C18 H18 119.2 . . ?
C20 C19 C18 121.9(2) . . ?
C20 C19 H19 119.1 . . ?
C18 C19 H19 119.1 . . ?
C19 C20 C21 117.5(2) . . ?
C19 C20 H20 121.3 . . ?
C21 C20 H20 121.3 . . ?
C16 C21 C20 119.71(19) . . ?
C16 C21 N2 108.62(17) . . ?
C20 C21 N2 131.65(19) . . ?
C23 C22 C27 120.39(19) . . ?
C23 C22 N5 130.96(19) . . ?
C27 C22 N5 108.56(18) . . ?
C24 C23 C22 117.4(2) . . ?
C24 C23 H23 121.3 . . ?
C22 C23 H23 121.3 . . ?
C23 C24 C25 121.5(2) . . ?
C23 C24 H24 119.3 . . ?
C25 C24 H24 119.3 . . ?
C26 C25 C24 121.8(2) . . ?
C26 C25 H25 119.1 . . ?
C24 C25 H25 119.1 . . ?
C25 C26 C27 116.5(2) . . ?
C25 C26 H26 121.8 . . ?
C27 C26 H26 121.8 . . ?
N4 C27 C26 131.59(19) . . ?
N4 C27 C22 105.96(18) . . ?
C26 C27 C22 122.4(2) . . ?
N4 C28 H28A 109.5 . . ?
N4 C28 H28B 109.5 . . ?
H28A C28 H28B 109.5 . . ?
N4 C28 H28C 109.5 . . ?
H28A C28 H28C 109.5 . . ?
H28B C28 H28C 109.5 . . ?
N5 C29 N4 111.73(18) . . ?
N5 C29 C30 126.05(19) . . ?
N4 C29 C30 122.15(18) . . ?
C29 C30 C31 115.00(18) . . ?
C29 C30 H30A 108.5 . . ?
C31 C30 H30A 108.5 . . ?
C29 C30 H30B 108.5 . . ?
C31 C30 H30B 108.5 . . ?
H30A C30 H30B 107.5 . . ?
N6 C31 C30 111.41(17) . . ?
N6 C31 H31A 109.3 . . ?
C30 C31 H31A 109.3 . . ?
N6 C31 H31B 109.3 . . ?
C30 C31 H31B 109.3 . . ?
H31A C31 H31B 108.0 . . ?
N6 C32 C33 125.68(19) . . ?
N6 C32 H32 117.2 . . ?
C33 C32 H32 117.2 . . ?
C34 C33 C32 120.94(19) . . ?
C34 C33 C42 119.90(18) . . ?
C32 C33 C42 119.08(19) . . ?
O5 C34 C33 124.94(19) . . ?
O5 C34 C35 116.36(19) . . ?
C33 C34 C35 118.68(19) . . ?
C36 C35 C34 121.4(2) . . ?
C36 C35 H35 119.3 . . ?
C34 C35 H35 119.3 . . ?
C35 C36 C37 121.8(2) . . ?
C35 C36 H36 119.1 . . ?
C37 C36 H36 119.1 . . ?
C38 C37 C36 121.3(2) . . ?
C38 C37 C42 119.7(2) . . ?
C36 C37 C42 119.0(2) . . ?
C39 C38 C37 121.2(2) . . ?
C39 C38 H38 119.4 . . ?
C37 C38 H38 119.4 . . ?
C38 C39 C40 119.5(2) . . ?
C38 C39 H39 120.3 . . ?
C40 C39 H39 120.3 . . ?
C41 C40 C39 120.6(2) . . ?
C41 C40 H40 119.7 . . ?
C39 C40 H40 119.7 . . ?
C40 C41 C42 121.5(2) . . ?
C40 C41 H41 119.2 . . ?
C42 C41 H41 119.2 . . ?
C41 C42 C37 117.4(2) . . ?
C41 C42 C33 123.45(19) . . ?
C37 C42 C33 119.1(2) . . ?
C14 N1 C16 107.79(16) . . ?
C14 N1 C15 126.15(17) . . ?
C16 N1 C15 126.04(17) . . ?
C14 N2 C21 105.37(17) . . ?
C14 N2 Cu1 124.92(14) . . ?
C21 N2 Cu1 129.67(13) . . ?
C11 N3 C12 117.62(17) . . ?
C11 N3 Cu1 125.17(14) . . ?
C12 N3 Cu1 117.03(13) . . ?
C29 N4 C27 108.08(17) . . ?
C29 N4 C28 125.86(18) . . ?
C27 N4 C28 125.78(18) . . ?
C29 N5 C22 105.65(17) . . ?
C29 N5 Cu2 125.19(14) . . ?
C22 N5 Cu2 128.99(14) . . ?
C32 N6 C31 118.97(18) . . ?
C32 N6 Cu2 124.27(14) . . ?
C31 N6 Cu2 116.71(14) . . ?
O3 N7 O4 122.8(2) . . ?
O3 N7 O2 119.24(19) . . ?
O4 N7 O2 117.98(18) . . ?
O7 N8 O8 122.87(19) . . ?
O7 N8 O6 119.21(18) . . ?
O8 N8 O6 117.92(18) . . ?
C9 O1 Cu1 128.24(13) . . ?
N7 O2 Cu1 105.42(12) . . ?
C34 O5 Cu2 125.20(13) . . ?
N8 O6 Cu2 106.59(12) . . ?
O1 Cu1 N3 92.51(7) . . ?
O1 Cu1 N2 161.02(7) . . ?
N3 Cu1 N2 94.47(7) . . ?
O1 Cu1 O2 86.88(6) . . ?
N3 Cu1 O2 155.78(7) . . ?
N2 Cu1 O2 93.82(6) . . ?
O5 Cu2 N6 93.11(7) . . ?
O5 Cu2 N5 159.63(7) . . ?
N6 Cu2 N5 93.58(7) . . ?
O5 Cu2 O6 88.50(6) . . ?
N6 Cu2 O6 157.44(7) . . ?
N5 Cu2 O6 92.63(7) . . ?

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
C6 C1 C2 C3 -1.1(3) . . . . ?
C10 C1 C2 C3 178.6(2) . . . . ?
C1 C2 C3 C4 0.4(3) . . . . ?
C2 C3 C4 C5 0.5(3) . . . . ?
C3 C4 C5 C6 -0.7(4) . . . . ?
C4 C5 C6 C1 -0.1(3) . . . . ?
C4 C5 C6 C7 -179.8(2) . . . . ?
C2 C1 C6 C5 1.0(3) . . . . ?
C10 C1 C6 C5 -178.80(19) . . . . ?
C2 C1 C6 C7 -179.35(19) . . . . ?
C10 C1 C6 C7 0.9(3) . . . . ?
C5 C6 C7 C8 -179.4(2) . . . . ?
C1 C6 C7 C8 0.9(3) . . . . ?
C6 C7 C8 C9 -1.2(3) . . . . ?
C7 C8 C9 O1 -178.4(2) . . . . ?
C7 C8 C9 C10 -0.3(3) . . . . ?
O1 C9 C10 C11 5.2(3) . . . . ?
C8 C9 C10 C11 -172.75(19) . . . . ?
O1 C9 C10 C1 -179.93(19) . . . . ?
C8 C9 C10 C1 2.1(3) . . . . ?
C2 C1 C10 C9 177.8(2) . . . . ?
C6 C1 C10 C9 -2.4(3) . . . . ?
C2 C1 C10 C11 -7.2(3) . . . . ?
C6 C1 C10 C11 172.52(19) . . . . ?
C9 C10 C11 N3 -5.9(3) . . . . ?
C1 C10 C11 N3 179.1(2) . . . . ?
N3 C12 C13 C14 60.5(3) . . . . ?
C12 C13 C14 N2 -28.7(3) . . . . ?
C12 C13 C14 N1 154.31(19) . . . . ?
N1 C16 C17 C18 178.6(2) . . . . ?
C21 C16 C17 C18 -2.2(3) . . . . ?
C16 C17 C18 C19 0.0(3) . . . . ?
C17 C18 C19 C20 1.5(3) . . . . ?
C18 C19 C20 C21 -0.9(3) . . . . ?
N1 C16 C21 C20 -177.76(19) . . . . ?
C17 C16 C21 C20 2.8(3) . . . . ?
N1 C16 C21 N2 0.5(2) . . . . ?
C17 C16 C21 N2 -178.91(19) . . . . ?
C19 C20 C21 C16 -1.2(3) . . . . ?
C19 C20 C21 N2 -179.0(2) . . . . ?
C27 C22 C23 C24 -2.1(3) . . . . ?
N5 C22 C23 C24 -178.2(2) . . . . ?
C22 C23 C24 C25 0.3(3) . . . . ?
C23 C24 C25 C26 0.9(3) . . . . ?
C24 C25 C26 C27 -0.3(3) . . . . ?
C25 C26 C27 N4 177.6(2) . . . . ?
C25 C26 C27 C22 -1.5(3) . . . . ?
C23 C22 C27 N4 -176.54(18) . . . . ?
N5 C22 C27 N4 0.4(2) . . . . ?
C23 C22 C27 C26 2.8(3) . . . . ?
N5 C22 C27 C26 179.70(18) . . . . ?
N5 C29 C30 C31 -23.8(3) . . . . ?
N4 C29 C30 C31 159.45(19) . . . . ?
C29 C30 C31 N6 57.7(2) . . . . ?
N6 C32 C33 C34 -14.4(3) . . . . ?
N6 C32 C33 C42 168.73(19) . . . . ?
C32 C33 C34 O5 4.5(3) . . . . ?
C42 C33 C34 O5 -178.70(18) . . . . ?
C32 C33 C34 C35 -173.74(19) . . . . ?
C42 C33 C34 C35 3.1(3) . . . . ?
O5 C34 C35 C36 -179.55(19) . . . . ?
C33 C34 C35 C36 -1.2(3) . . . . ?
C34 C35 C36 C37 -1.1(3) . . . . ?
C35 C36 C37 C38 -178.5(2) . . . . ?
C35 C36 C37 C42 1.3(3) . . . . ?
C36 C37 C38 C39 178.7(2) . . . . ?
C42 C37 C38 C39 -1.1(3) . . . . ?
C37 C38 C39 C40 -0.7(3) . . . . ?
C38 C39 C40 C41 1.4(3) . . . . ?
C39 C40 C41 C42 -0.3(3) . . . . ?
C40 C41 C42 C37 -1.5(3) . . . . ?
C40 C41 C42 C33 -179.66(19) . . . . ?
C38 C37 C42 C41 2.2(3) . . . . ?
C36 C37 C42 C41 -177.64(19) . . . . ?
C38 C37 C42 C33 -179.59(18) . . . . ?
C36 C37 C42 C33 0.6(3) . . . . ?
C34 C33 C42 C41 175.34(19) . . . . ?
C32 C33 C42 C41 -7.8(3) . . . . ?
C34 C33 C42 C37 -2.8(3) . . . . ?
C32 C33 C42 C37 174.06(18) . . . . ?
N2 C14 N1 C16 -0.1(2) . . . . ?
C13 C14 N1 C16 177.26(19) . . . . ?
N2 C14 N1 C15 -178.51(19) . . . . ?
C13 C14 N1 C15 -1.1(3) . . . . ?
C17 C16 N1 C14 179.1(2) . . . . ?
C21 C16 N1 C14 -0.2(2) . . . . ?
C17 C16 N1 C15 -2.5(4) . . . . ?
C21 C16 N1 C15 178.15(19) . . . . ?
N1 C14 N2 C21 0.4(2) . . . . ?
C13 C14 N2 C21 -176.8(2) . . . . ?
N1 C14 N2 Cu1 178.51(13) . . . . ?
C13 C14 N2 Cu1 1.3(3) . . . . ?
C16 C21 N2 C14 -0.6(2) . . . . ?
C20 C21 N2 C14 177.4(2) . . . . ?
C16 C21 N2 Cu1 -178.52(14) . . . . ?
C20 C21 N2 Cu1 -0.6(3) . . . . ?
C10 C11 N3 C12 171.9(2) . . . . ?
C10 C11 N3 Cu1 -3.1(3) . . . . ?
C13 C12 N3 C11 120.8(2) . . . . ?
C13 C12 N3 Cu1 -63.8(2) . . . . ?
N5 C29 N4 C27 -1.4(2) . . . . ?
C30 C29 N4 C27 175.83(18) . . . . ?
N5 C29 N4 C28 -175.60(19) . . . . ?
C30 C29 N4 C28 1.6(3) . . . . ?
C26 C27 N4 C29 -178.7(2) . . . . ?
C22 C27 N4 C29 0.5(2) . . . . ?
C26 C27 N4 C28 -4.4(3) . . . . ?
C22 C27 N4 C28 174.79(19) . . . . ?
N4 C29 N5 C22 1.6(2) . . . . ?
C30 C29 N5 C22 -175.50(19) . . . . ?
N4 C29 N5 Cu2 177.12(13) . . . . ?
C30 C29 N5 Cu2 0.1(3) . . . . ?
C23 C22 N5 C29 175.3(2) . . . . ?
C27 C22 N5 C29 -1.2(2) . . . . ?
C23 C22 N5 Cu2 0.0(3) . . . . ?
C27 C22 N5 Cu2 -176.51(14) . . . . ?
C33 C32 N6 C31 177.25(19) . . . . ?
C33 C32 N6 Cu2 -0.2(3) . . . . ?
C30 C31 N6 C32 115.0(2) . . . . ?
C30 C31 N6 Cu2 -67.4(2) . . . . ?
C10 C9 O1 Cu1 4.9(3) . . . . ?
C8 C9 O1 Cu1 -177.18(14) . . . . ?
O3 N7 O2 Cu1 172.17(15) . . . . ?
O4 N7 O2 Cu1 -7.9(2) . . . . ?
C33 C34 O5 Cu2 19.2(3) . . . . ?
C35 C34 O5 Cu2 -162.54(14) . . . . ?
O7 N8 O6 Cu2 -178.84(16) . . . . ?
O8 N8 O6 Cu2 2.0(2) . . . . ?
C9 O1 Cu1 N3 -10.26(18) . . . . ?
C9 O1 Cu1 N2 101.3(2) . . . . ?
C9 O1 Cu1 O2 -166.01(18) . . . . ?
C11 N3 Cu1 O1 9.23(18) . . . . ?
C12 N3 Cu1 O1 -165.82(15) . . . . ?
C11 N3 Cu1 N2 -153.11(18) . . . . ?
C12 N3 Cu1 N2 31.84(16) . . . . ?
C11 N3 Cu1 O2 97.2(2) . . . . ?
C12 N3 Cu1 O2 -77.8(2) . . . . ?
C14 N2 Cu1 O1 -113.0(2) . . . . ?
C21 N2 Cu1 O1 64.6(3) . . . . ?
C14 N2 Cu1 N3 -1.73(18) . . . . ?
C21 N2 Cu1 N3 175.86(18) . . . . ?
C14 N2 Cu1 O2 155.49(17) . . . . ?
C21 N2 Cu1 O2 -26.91(18) . . . . ?
N7 O2 Cu1 O1 115.81(12) . . . . ?
N7 O2 Cu1 N3 26.6(2) . . . . ?
N7 O2 Cu1 N2 -83.19(12) . . . . ?
C34 O5 Cu2 N6 -25.61(17) . . . . ?
C34 O5 Cu2 N5 83.4(3) . . . . ?
C34 O5 Cu2 O6 176.91(16) . . . . ?
C32 N6 Cu2 O5 16.35(18) . . . . ?
C31 N6 Cu2 O5 -161.14(15) . . . . ?
C32 N6 Cu2 N5 -144.40(17) . . . . ?
C31 N6 Cu2 N5 38.12(15) . . . . ?
C32 N6 Cu2 O6 109.9(2) . . . . ?
C31 N6 Cu2 O6 -67.6(2) . . . . ?
C29 N5 Cu2 O5 -114.4(2) . . . . ?
C22 N5 Cu2 O5 60.1(3) . . . . ?
C29 N5 Cu2 N6 -5.45(17) . . . . ?
C22 N5 Cu2 N6 169.05(17) . . . . ?
C29 N5 Cu2 O6 152.84(17) . . . . ?
C22 N5 Cu2 O6 -32.65(17) . . . . ?
N8 O6 Cu2 O5 103.28(12) . . . . ?
N8 O6 Cu2 N6 8.8(2) . . . . ?
N8 O6 Cu2 N5 -97.07(13) . . . . ?

_diffrn_measured_fraction_theta_max 0.998
_diffrn_reflns_theta_full        26.00
_diffrn_measured_fraction_theta_full 0.998
_refine_diff_density_max         0.307
_refine_diff_density_min         -0.475
_refine_diff_density_rms         0.059
_database_code_depnum_ccdc_archive 'CCDC 932005'
#######################################################################
#
#                 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_shelxl2
#TrackingRef 'R2KPM2.cif'


_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C21 H18 Cl Cu N3 O'
_chemical_formula_sum            'C21 H18 Cl Cu N3 O'
_chemical_formula_weight         427.37

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           monoclinic
_symmetry_space_group_name_H-M   'P 21/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                   8.2057(6)
_cell_length_b                   23.5851(16)
_cell_length_c                   9.7520(9)
_cell_angle_alpha                90.00
_cell_angle_beta                 106.423(8)
_cell_angle_gamma                90.00
_cell_volume                     1810.3(2)
_cell_formula_units_Z            4
_cell_measurement_temperature    298(2)
_cell_measurement_reflns_used    ?
_cell_measurement_theta_min      ?
_cell_measurement_theta_max      ?

_exptl_crystal_description       ?
_exptl_crystal_colour            ?
_exptl_crystal_size_max          0.10
_exptl_crystal_size_mid          0.08
_exptl_crystal_size_min          0.06
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.568
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             876
_exptl_absorpt_coefficient_mu    1.370
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.8751
_exptl_absorpt_correction_T_max  0.9223
_exptl_absorpt_process_details   sadabs

_exptl_special_details           
;
?
;

_diffrn_ambient_temperature      298(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            15920
_diffrn_reflns_av_R_equivalents  0.0559
_diffrn_reflns_av_sigmaI/netI    0.0506
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       -29
_diffrn_reflns_limit_k_max       29
_diffrn_reflns_limit_l_min       -10
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_theta_min         3.00
_diffrn_reflns_theta_max         26.00
_reflns_number_total             3544
_reflns_number_gt                2970
_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)+(0.0342P)²+3.5599P] where P=(Fo²+2Fc²)/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         3544
_refine_ls_number_parameters     245
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0772
_refine_ls_R_factor_gt           0.0617
_refine_ls_wR_factor_ref         0.1302
_refine_ls_wR_factor_gt          0.1245
_refine_ls_goodness_of_fit_ref   1.194
_refine_ls_restrained_S_all      1.194
_refine_ls_shift/su_max          0.002
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C 0.3994(6) 0.12230(19) 0.4236(5) 0.0321(10) Uani 1 1 d . . .
C2 C 0.4893(6) 0.1597(2) 0.5284(6) 0.0397(12) Uani 1 1 d . . .
H2 H 0.5016 0.1530 0.6248 0.048 Uiso 1 1 calc R . .
C3 C 0.5594(6) 0.2070(2) 0.4841(6) 0.0469(13) Uani 1 1 d . . .
H3 H 0.6212 0.2323 0.5522 0.056 Uiso 1 1 calc R . .
C4 C 0.5397(7) 0.2178(2) 0.3398(7) 0.0532(15) Uani 1 1 d . . .
H4 H 0.5889 0.2501 0.3142 0.064 Uiso 1 1 calc R . .
C5 C 0.4492(7) 0.1818(2) 0.2339(6) 0.0457(13) Uani 1 1 d . . .
H5 H 0.4353 0.1891 0.1376 0.055 Uiso 1 1 calc R . .
C6 C 0.3805(6) 0.1343(2) 0.2790(5) 0.0338(11) Uani 1 1 d . . .
C7 C 0.2279(7) 0.0859(2) 0.0468(5) 0.0437(12) Uani 1 1 d . . .
H7A H 0.2586 0.0493 0.0188 0.066 Uiso 1 1 calc R . .
H7B H 0.2820 0.1149 0.0061 0.066 Uiso 1 1 calc R . .
H7C H 0.1069 0.0905 0.0133 0.066 Uiso 1 1 calc R . .
C8 C 0.2489(6) 0.05439(19) 0.2981(5) 0.0317(10) Uani 1 1 d . . .
C9 C 0.1485(6) 0.0020(2) 0.2583(5) 0.0355(11) Uani 1 1 d . . .
H9A H 0.1396 -0.0071 0.1595 0.043 Uiso 1 1 calc R . .
H9B H 0.0346 0.0085 0.2658 0.043 Uiso 1 1 calc R . .
C10 C 0.2263(6) -0.04782(19) 0.3520(5) 0.0342(11) Uani 1 1 d . . .
H10A H 0.1640 -0.0820 0.3137 0.041 Uiso 1 1 calc R . .
H10B H 0.3426 -0.0527 0.3490 0.041 Uiso 1 1 calc R . .
C11 C 0.1851(5) -0.08426(18) 0.5641(5) 0.0289(9) Uani 1 1 d . . .
H11 H 0.1435 -0.1153 0.5060 0.035 Uiso 1 1 calc R . .
C12 C 0.1971(5) -0.09061(18) 0.7127(5) 0.0280(9) Uani 1 1 d . . .
C13 C 0.1214(5) -0.13897(18) 0.7587(5) 0.0286(10) Uani 1 1 d . . .
C14 C 0.0031(6) -0.17469(19) 0.6648(5) 0.0351(11) Uani 1 1 d . . .
H14 H -0.0287 -0.1666 0.5675 0.042 Uiso 1 1 calc R . .
C15 C -0.0665(6) -0.2207(2) 0.7120(6) 0.0399(12) Uani 1 1 d . . .
H15 H -0.1419 -0.2440 0.6468 0.048 Uiso 1 1 calc R . .
C16 C -0.0244(7) -0.2330(2) 0.8583(6) 0.0472(13) Uani 1 1 d . . .
H16 H -0.0711 -0.2646 0.8904 0.057 Uiso 1 1 calc R . .
C17 C 0.0843(6) -0.1988(2) 0.9529(5) 0.0405(12) Uani 1 1 d . . .
H17 H 0.1095 -0.2065 1.0502 0.049 Uiso 1 1 calc R . .
C18 C 0.1600(6) -0.15163(19) 0.9058(5) 0.0334(10) Uani 1 1 d . . .
C19 C 0.2749(6) -0.1151(2) 1.0035(5) 0.0393(11) Uani 1 1 d . . .
H19 H 0.3053 -0.1240 1.1003 0.047 Uiso 1 1 calc R . .
C20 C 0.3411(6) -0.0683(2) 0.9616(5) 0.0353(11) Uani 1 1 d . . .
H20 H 0.4138 -0.0454 1.0296 0.042 Uiso 1 1 calc R . .
C21 C 0.3007(6) -0.05329(19) 0.8128(5) 0.0317(10) Uani 1 1 d . . .
N1 N 0.2834(5) 0.09057(16) 0.2032(4) 0.0344(9) Uani 1 1 d . . .
N2 N 0.3154(5) 0.07172(15) 0.4315(4) 0.0308(8) Uani 1 1 d . . .
N3 N 0.2250(5) -0.04069(15) 0.5018(4) 0.0327(9) Uani 1 1 d . . .
O1 O 0.3660(4) -0.00693(14) 0.7799(3) 0.0402(8) Uani 1 1 d . . .
Cl1 Cl 0.21068(18) 0.10915(5) 0.70358(13) 0.0457(3) Uani 1 1 d . . .
Cu1 Cu 0.28728(7) 0.03214(2) 0.60215(6) 0.03124(18) Uani 1 1 d . . .


_geom_special_details            
;
All esds (except the esd in the dihedral angle between two l.s. planes)
are estimated using the full covariance matrix. The cell esds are taken
into account individually in the estimation of esds in distances, angles
and torsion angles; correlations between esds in cell parameters are only
used when they are defined by crystal symmetry. An approximate (isotropic)
treatment of cell esds is used for estimating esds involving l.s. planes.
;

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
C1 N2 1.391(6) . ?
C1 C2 1.393(7) . ?
C1 C6 1.403(6) . ?
C2 C3 1.380(7) . ?
C2 H2 0.9300 . ?
C3 C4 1.393(8) . ?
C3 H3 0.9300 . ?
C4 C5 1.380(8) . ?
C4 H4 0.9300 . ?
C5 C6 1.381(7) . ?
C5 H5 0.9300 . ?
C6 N1 1.383(6) . ?
C7 N1 1.467(6) . ?
C7 H7A 0.9600 . ?
C7 H7B 0.9600 . ?
C7 H7C 0.9600 . ?
C8 N2 1.325(6) . ?
C8 N1 1.347(6) . ?
C8 C9 1.475(6) . ?
C9 C10 1.515(6) . ?
C9 H9A 0.9700 . ?
C9 H9B 0.9700 . ?
C10 N3 1.474(6) . ?
C10 H10A 0.9700 . ?
C10 H10B 0.9700 . ?
C11 N3 1.283(5) . ?
C11 C12 1.432(6) . ?
C11 H11 0.9300 . ?
C12 C21 1.408(6) . ?
C12 C13 1.430(6) . ?
C13 C14 1.410(6) . ?
C13 C18 1.411(6) . ?
C14 C15 1.366(6) . ?
C14 H14 0.9300 . ?
C15 C16 1.400(7) . ?
C15 H15 0.9300 . ?
C16 C17 1.353(7) . ?
C16 H16 0.9300 . ?
C17 C18 1.413(6) . ?
C17 H17 0.9300 . ?
C18 C19 1.425(7) . ?
C19 C20 1.343(7) . ?
C19 H19 0.9300 . ?
C20 C21 1.438(6) . ?
C20 H20 0.9300 . ?
C21 O1 1.297(5) . ?
N2 Cu1 1.978(4) . ?
N3 Cu1 1.972(4) . ?
O1 Cu1 1.907(3) . ?
Cl1 Cu1 2.2414(13) . ?

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
N2 C1 C2 132.1(4) . . ?
N2 C1 C6 108.2(4) . . ?
C2 C1 C6 119.7(4) . . ?
C3 C2 C1 117.6(5) . . ?
C3 C2 H2 121.2 . . ?
C1 C2 H2 121.2 . . ?
C2 C3 C4 121.6(5) . . ?
C2 C3 H3 119.2 . . ?
C4 C3 H3 119.2 . . ?
C5 C4 C3 121.8(5) . . ?
C5 C4 H4 119.1 . . ?
C3 C4 H4 119.1 . . ?
C4 C5 C6 116.3(5) . . ?
C4 C5 H5 121.9 . . ?
C6 C5 H5 121.9 . . ?
C5 C6 N1 131.3(5) . . ?
C5 C6 C1 123.0(5) . . ?
N1 C6 C1 105.7(4) . . ?
N1 C7 H7A 109.5 . . ?
N1 C7 H7B 109.5 . . ?
H7A C7 H7B 109.5 . . ?
N1 C7 H7C 109.5 . . ?
H7A C7 H7C 109.5 . . ?
H7B C7 H7C 109.5 . . ?
N2 C8 N1 111.8(4) . . ?
N2 C8 C9 124.2(4) . . ?
N1 C8 C9 124.1(4) . . ?
C8 C9 C10 112.5(4) . . ?
C8 C9 H9A 109.1 . . ?
C10 C9 H9A 109.1 . . ?
C8 C9 H9B 109.1 . . ?
C10 C9 H9B 109.1 . . ?
H9A C9 H9B 107.8 . . ?
N3 C10 C9 112.9(4) . . ?
N3 C10 H10A 109.0 . . ?
C9 C10 H10A 109.0 . . ?
N3 C10 H10B 109.0 . . ?
C9 C10 H10B 109.0 . . ?
H10A C10 H10B 107.8 . . ?
N3 C11 C12 127.5(4) . . ?
N3 C11 H11 116.2 . . ?
C12 C11 H11 116.2 . . ?
C21 C12 C13 120.8(4) . . ?
C21 C12 C11 119.4(4) . . ?
C13 C12 C11 119.3(4) . . ?
C14 C13 C18 116.7(4) . . ?
C14 C13 C12 123.6(4) . . ?
C18 C13 C12 119.7(4) . . ?
C15 C14 C13 122.2(5) . . ?
C15 C14 H14 118.9 . . ?
C13 C14 H14 118.9 . . ?
C14 C15 C16 120.1(5) . . ?
C14 C15 H15 119.9 . . ?
C16 C15 H15 119.9 . . ?
C17 C16 C15 119.7(5) . . ?
C17 C16 H16 120.1 . . ?
C15 C16 H16 120.1 . . ?
C16 C17 C18 120.9(5) . . ?
C16 C17 H17 119.5 . . ?
C18 C17 H17 119.5 . . ?
C13 C18 C17 120.3(4) . . ?
C13 C18 C19 117.8(4) . . ?
C17 C18 C19 121.9(4) . . ?
C20 C19 C18 122.8(4) . . ?
C20 C19 H19 118.6 . . ?
C18 C19 H19 118.6 . . ?
C19 C20 C21 120.8(4) . . ?
C19 C20 H20 119.6 . . ?
C21 C20 H20 119.6 . . ?
O1 C21 C12 124.5(4) . . ?
O1 C21 C20 117.6(4) . . ?
C12 C21 C20 117.9(4) . . ?
C8 N1 C6 107.8(4) . . ?
C8 N1 C7 127.1(4) . . ?
C6 N1 C7 125.0(4) . . ?
C8 N2 C1 106.5(4) . . ?
C8 N2 Cu1 124.5(3) . . ?
C1 N2 Cu1 129.0(3) . . ?
C11 N3 C10 116.9(4) . . ?
C11 N3 Cu1 121.9(3) . . ?
C10 N3 Cu1 121.2(3) . . ?
C21 O1 Cu1 125.1(3) . . ?
O1 Cu1 N3 90.21(14) . . ?
O1 Cu1 N2 154.51(15) . . ?
N3 Cu1 N2 93.96(15) . . ?
O1 Cu1 Cl1 93.19(11) . . ?
N3 Cu1 Cl1 149.26(12) . . ?
N2 Cu1 Cl1 95.91(11) . . ?

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
N2 C1 C2 C3 179.8(5) . . . . ?
C6 C1 C2 C3 -1.3(7) . . . . ?
C1 C2 C3 C4 0.9(7) . . . . ?
C2 C3 C4 C5 0.1(8) . . . . ?
C3 C4 C5 C6 -0.5(8) . . . . ?
C4 C5 C6 N1 179.4(5) . . . . ?
C4 C5 C6 C1 0.1(7) . . . . ?
N2 C1 C6 C5 -180.0(4) . . . . ?
C2 C1 C6 C5 0.8(7) . . . . ?
N2 C1 C6 N1 0.6(5) . . . . ?
C2 C1 C6 N1 -178.6(4) . . . . ?
N2 C8 C9 C10 -43.6(6) . . . . ?
N1 C8 C9 C10 136.7(4) . . . . ?
C8 C9 C10 N3 66.1(5) . . . . ?
N3 C11 C12 C21 -17.9(7) . . . . ?
N3 C11 C12 C13 170.1(4) . . . . ?
C21 C12 C13 C14 173.4(4) . . . . ?
C11 C12 C13 C14 -14.8(6) . . . . ?
C21 C12 C13 C18 -4.2(6) . . . . ?
C11 C12 C13 C18 167.6(4) . . . . ?
C18 C13 C14 C15 -2.6(6) . . . . ?
C12 C13 C14 C15 179.7(4) . . . . ?
C13 C14 C15 C16 1.7(7) . . . . ?
C14 C15 C16 C17 0.6(7) . . . . ?
C15 C16 C17 C18 -1.8(8) . . . . ?
C14 C13 C18 C17 1.4(6) . . . . ?
C12 C13 C18 C17 179.1(4) . . . . ?
C14 C13 C18 C19 -177.9(4) . . . . ?
C12 C13 C18 C19 -0.2(6) . . . . ?
C16 C17 C18 C13 0.8(7) . . . . ?
C16 C17 C18 C19 -180.0(5) . . . . ?
C13 C18 C19 C20 2.9(7) . . . . ?
C17 C18 C19 C20 -176.3(5) . . . . ?
C18 C19 C20 C21 -1.3(7) . . . . ?
C13 C12 C21 O1 -175.9(4) . . . . ?
C11 C12 C21 O1 12.2(7) . . . . ?
C13 C12 C21 C20 5.8(6) . . . . ?
C11 C12 C21 C20 -166.0(4) . . . . ?
C19 C20 C21 O1 178.5(4) . . . . ?
C19 C20 C21 C12 -3.2(7) . . . . ?
N2 C8 N1 C6 0.6(5) . . . . ?
C9 C8 N1 C6 -179.7(4) . . . . ?
N2 C8 N1 C7 -178.6(4) . . . . ?
C9 C8 N1 C7 1.1(7) . . . . ?
C5 C6 N1 C8 179.9(5) . . . . ?
C1 C6 N1 C8 -0.7(5) . . . . ?
C5 C6 N1 C7 -0.8(8) . . . . ?
C1 C6 N1 C7 178.5(4) . . . . ?
N1 C8 N2 C1 -0.3(5) . . . . ?
C9 C8 N2 C1 -180.0(4) . . . . ?
N1 C8 N2 Cu1 177.7(3) . . . . ?
C9 C8 N2 Cu1 -1.9(6) . . . . ?
C2 C1 N2 C8 178.8(5) . . . . ?
C6 C1 N2 C8 -0.2(5) . . . . ?
C2 C1 N2 Cu1 0.9(7) . . . . ?
C6 C1 N2 Cu1 -178.1(3) . . . . ?
C12 C11 N3 C10 170.7(4) . . . . ?
C12 C11 N3 Cu1 -7.9(6) . . . . ?
C9 C10 N3 C11 138.0(4) . . . . ?
C9 C10 N3 Cu1 -43.4(5) . . . . ?
C12 C21 O1 Cu1 19.3(6) . . . . ?
C20 C21 O1 Cu1 -162.5(3) . . . . ?
C21 O1 Cu1 N3 -33.7(4) . . . . ?
C21 O1 Cu1 N2 -133.4(4) . . . . ?
C21 O1 Cu1 Cl1 115.8(4) . . . . ?
C11 N3 Cu1 O1 27.5(4) . . . . ?
C10 N3 Cu1 O1 -151.1(3) . . . . ?
C11 N3 Cu1 N2 -177.7(3) . . . . ?
C10 N3 Cu1 N2 3.8(3) . . . . ?
C11 N3 Cu1 Cl1 -69.1(4) . . . . ?
C10 N3 Cu1 Cl1 112.3(3) . . . . ?
C8 N2 Cu1 O1 118.8(4) . . . . ?
C1 N2 Cu1 O1 -63.6(5) . . . . ?
C8 N2 Cu1 N3 20.0(4) . . . . ?
C1 N2 Cu1 N3 -162.4(4) . . . . ?
C8 N2 Cu1 Cl1 -130.8(3) . . . . ?
C1 N2 Cu1 Cl1 46.7(4) . . . . ?

_diffrn_measured_fraction_theta_max 0.999
_diffrn_reflns_theta_full        26.00
_diffrn_measured_fraction_theta_full 0.999
_refine_diff_density_max         0.577
_refine_diff_density_min         -0.320
_refine_diff_density_rms         0.082
_database_code_depnum_ccdc_archive 'CCDC 932003'
