# 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.
#
data_1

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C26 H19 N3 O3 Zn'
_chemical_formula_weight         486.81

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'
Zn Zn 0.2839 1.4301 '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                   11.5221(7)
_cell_length_b                   21.9315(13)
_cell_length_c                   8.3869(5)
_cell_angle_alpha                90.00
_cell_angle_beta                 94.3740(10)
_cell_angle_gamma                90.00
_cell_volume                     2113.2(2)
_cell_formula_units_Z            4
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    3699
_cell_measurement_theta_min      2.61
_cell_measurement_theta_max      26.64

_exptl_crystal_description       block
_exptl_crystal_colour            yellow
_exptl_crystal_size_max          0.17
_exptl_crystal_size_mid          0.13
_exptl_crystal_size_min          0.10
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.530
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1000
_exptl_absorpt_coefficient_mu    1.198
_exptl_absorpt_correction_type   Multi-scan
_exptl_absorpt_correction_T_min  0.8223
_exptl_absorpt_correction_T_max  0.8896
_exptl_absorpt_process_details   SADABS

_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  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            12727
_diffrn_reflns_av_R_equivalents  0.0313
_diffrn_reflns_av_sigmaI/netI    0.0407
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_k_min       -25
_diffrn_reflns_limit_k_max       28
_diffrn_reflns_limit_l_min       -10
_diffrn_reflns_limit_l_max       10
_diffrn_reflns_theta_min         1.77
_diffrn_reflns_theta_max         27.55
_reflns_number_total             4806
_reflns_number_gt                3732
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'Bruker SMART'
_computing_cell_refinement       'Bruker SMART'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'

_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)+(0.0471P)²+0.4329P] 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         4806
_refine_ls_number_parameters     299
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0520
_refine_ls_R_factor_gt           0.0358
_refine_ls_wR_factor_ref         0.0944
_refine_ls_wR_factor_gt          0.0874
_refine_ls_goodness_of_fit_ref   1.034
_refine_ls_restrained_S_all      1.034
_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 1.0891(2) 0.15393(10) 0.3712(3) 0.0299(5) Uani 1 1 d . . .
C2 C 1.1801(2) 0.11696(12) 0.3268(3) 0.0396(6) Uani 1 1 d . . .
H2 H 1.1833 0.0756 0.3518 0.048 Uiso 1 1 calc R . .
C3 C 1.2651(2) 0.14463(13) 0.2440(4) 0.0479(7) Uani 1 1 d . . .
H3 H 1.3279 0.1215 0.2154 0.058 Uiso 1 1 calc R . .
C4 C 1.2593(3) 0.20626(14) 0.2021(4) 0.0513(7) Uani 1 1 d . . .
H4 H 1.3179 0.2229 0.1454 0.062 Uiso 1 1 calc R . .
C5 C 1.1695(2) 0.24274(12) 0.2422(3) 0.0433(7) Uani 1 1 d . . .
H5 H 1.1652 0.2837 0.2133 0.052 Uiso 1 1 calc R . .
C6 C 1.0849(2) 0.21524(11) 0.3290(3) 0.0322(5) Uani 1 1 d . . .
C7 C 0.9302(2) 0.19177(10) 0.4547(3) 0.0280(5) Uani 1 1 d . . .
C8 C 0.8174(2) 0.20081(10) 0.5223(3) 0.0292(5) Uani 1 1 d . . .
C9 C 0.7357(2) 0.15318(10) 0.5312(3) 0.0300(5) Uani 1 1 d . . .
C10 C 0.6286(2) 0.16567(12) 0.5909(3) 0.0410(6) Uani 1 1 d . . .
H10 H 0.5744 0.1345 0.5973 0.049 Uiso 1 1 calc R . .
C11 C 0.6019(2) 0.22357(14) 0.6407(4) 0.0485(7) Uani 1 1 d . . .
H11 H 0.5303 0.2311 0.6809 0.058 Uiso 1 1 calc R . .
C12 C 0.6812(2) 0.27033(12) 0.6311(3) 0.0447(7) Uani 1 1 d . . .
H12 H 0.6633 0.3093 0.6654 0.054 Uiso 1 1 calc R . .
C13 C 0.7870(2) 0.25899(11) 0.5704(3) 0.0368(6) Uani 1 1 d . . .
H13 H 0.8392 0.2909 0.5614 0.044 Uiso 1 1 calc R . .
C14 C 0.6860(2) 0.06190(10) 0.4034(3) 0.0295(5) Uani 1 1 d . . .
H14 H 0.6143 0.0809 0.3827 0.035 Uiso 1 1 calc R . .
C15 C 0.69496(19) 0.00133(10) 0.3419(3) 0.0273(5) Uani 1 1 d . . .
C16 C 0.80137(19) -0.03058(10) 0.3447(3) 0.0252(5) Uani 1 1 d . . .
C17 C 0.8057(2) -0.08598(11) 0.2560(3) 0.0325(5) Uani 1 1 d . . .
H17 H 0.8756 -0.1071 0.2565 0.039 Uiso 1 1 calc R . .
C18 C 0.7108(2) -0.10842(12) 0.1715(3) 0.0362(6) Uani 1 1 d . . .
H18 H 0.7179 -0.1439 0.1122 0.043 Uiso 1 1 calc R . .
C19 C 0.6010(2) -0.07971(11) 0.1704(3) 0.0328(5) Uani 1 1 d . . .
C20 C 0.5025(2) -0.10447(14) 0.0832(3) 0.0452(7) Uani 1 1 d . . .
H20 H 0.5103 -0.1397 0.0232 0.054 Uiso 1 1 calc R . .
C21 C 0.3959(3) -0.07741(14) 0.0858(4) 0.0514(7) Uani 1 1 d . . .
H21 H 0.3318 -0.0938 0.0267 0.062 Uiso 1 1 calc R . .
C22 C 0.3836(2) -0.02526(14) 0.1769(4) 0.0504(7) Uani 1 1 d . . .
H22 H 0.3108 -0.0072 0.1798 0.060 Uiso 1 1 calc R . .
C23 C 0.4783(2) -0.00003(12) 0.2631(3) 0.0414(6) Uani 1 1 d . . .
H23 H 0.4678 0.0343 0.3254 0.050 Uiso 1 1 calc R . .
C24 C 0.59131(19) -0.02514(11) 0.2591(3) 0.0304(5) Uani 1 1 d . . .
C25 C 0.92026(19) 0.08789(11) 0.8796(3) 0.0304(5) Uani 1 1 d . . .
C26 C 0.9147(3) 0.07118(14) 1.0522(3) 0.0477(7) Uani 1 1 d . . .
H26A H 0.9904 0.0587 1.0958 0.072 Uiso 1 1 calc R . .
H26B H 0.8605 0.0383 1.0610 0.072 Uiso 1 1 calc R . .
H26C H 0.8896 0.1059 1.1103 0.072 Uiso 1 1 calc R . .
N1 N 0.99061(16) 0.13989(8) 0.4510(2) 0.0284(4) Uani 1 1 d . . .
N2 N 0.98478(17) 0.23809(9) 0.3852(2) 0.0335(5) Uani 1 1 d . . .
H2A H 0.9611 0.2752 0.3775 0.040 Uiso 1 1 calc R . .
N3 N 0.76489(16) 0.09340(8) 0.4839(2) 0.0283(4) Uani 1 1 d . . .
O1 O 0.89832(12) -0.01292(7) 0.42484(19) 0.0281(3) Uani 1 1 d . . .
O2 O 0.91187(14) 0.04394(7) 0.7799(2) 0.0328(4) Uani 1 1 d . . .
O3 O 0.93442(17) 0.14127(8) 0.8387(2) 0.0453(5) Uani 1 1 d . . .
Zn1 Zn 0.93436(2) 0.062064(11) 0.55448(3) 0.02643(9) 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 C6 1.390(3) . ?
C1 N1 1.395(3) . ?
C1 C2 1.398(3) . ?
C2 C3 1.383(4) . ?
C2 H2 0.9300 . ?
C3 C4 1.397(4) . ?
C3 H3 0.9300 . ?
C4 C5 1.369(4) . ?
C4 H4 0.9300 . ?
C5 C6 1.397(3) . ?
C5 H5 0.9300 . ?
C6 N2 1.374(3) . ?
C7 N1 1.335(3) . ?
C7 N2 1.350(3) . ?
C7 C8 1.471(3) . ?
C8 C13 1.391(3) . ?
C8 C9 1.412(3) . ?
C9 C10 1.393(3) . ?
C9 N3 1.418(3) . ?
C10 C11 1.379(4) . ?
C10 H10 0.9300 . ?
C11 C12 1.380(4) . ?
C11 H11 0.9300 . ?
C12 C13 1.379(4) . ?
C12 H12 0.9300 . ?
C13 H13 0.9300 . ?
C14 N3 1.291(3) . ?
C14 C15 1.432(3) . ?
C14 H14 0.9300 . ?
C15 C16 1.410(3) . ?
C15 C24 1.456(3) . ?
C16 O1 1.317(2) . ?
C16 C17 1.427(3) . ?
C17 C18 1.350(3) . ?
C17 H17 0.9300 . ?
C18 C19 1.413(3) . ?
C18 H18 0.9300 . ?
C19 C20 1.411(3) . ?
C19 C24 1.418(3) . ?
C20 C21 1.365(4) . ?
C20 H20 0.9300 . ?
C21 C22 1.389(4) . ?
C21 H21 0.9300 . ?
C22 C23 1.378(4) . ?
C22 H22 0.9300 . ?
C23 C24 1.416(3) . ?
C23 H23 0.9300 . ?
C25 O3 1.234(3) . ?
C25 O2 1.275(3) . ?
C25 C26 1.499(4) . ?
C26 H26A 0.9600 . ?
C26 H26B 0.9600 . ?
C26 H26C 0.9600 . ?
N1 Zn1 2.0424(18) . ?
N2 H2A 0.8600 . ?
N3 Zn1 2.1117(19) . ?
O1 Zn1 1.9975(15) . ?
O1 Zn1 2.2039(15) 3_756 ?
O2 Zn1 1.9686(17) . ?
Zn1 O1 2.2039(15) 3_756 ?

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
C6 C1 N1 108.8(2) . . ?
C6 C1 C2 120.3(2) . . ?
N1 C1 C2 130.8(2) . . ?
C3 C2 C1 116.9(2) . . ?
C3 C2 H2 121.5 . . ?
C1 C2 H2 121.5 . . ?
C2 C3 C4 121.9(3) . . ?
C2 C3 H3 119.0 . . ?
C4 C3 H3 119.0 . . ?
C5 C4 C3 121.7(3) . . ?
C5 C4 H4 119.1 . . ?
C3 C4 H4 119.1 . . ?
C4 C5 C6 116.5(2) . . ?
C4 C5 H5 121.8 . . ?
C6 C5 H5 121.8 . . ?
N2 C6 C1 106.2(2) . . ?
N2 C6 C5 131.2(2) . . ?
C1 C6 C5 122.6(2) . . ?
N1 C7 N2 111.7(2) . . ?
N1 C7 C8 127.0(2) . . ?
N2 C7 C8 121.3(2) . . ?
C13 C8 C9 118.7(2) . . ?
C13 C8 C7 119.0(2) . . ?
C9 C8 C7 122.2(2) . . ?
C10 C9 C8 119.0(2) . . ?
C10 C9 N3 121.2(2) . . ?
C8 C9 N3 119.7(2) . . ?
C11 C10 C9 120.9(3) . . ?
C11 C10 H10 119.5 . . ?
C9 C10 H10 119.5 . . ?
C10 C11 C12 120.2(3) . . ?
C10 C11 H11 119.9 . . ?
C12 C11 H11 119.9 . . ?
C13 C12 C11 119.7(2) . . ?
C13 C12 H12 120.2 . . ?
C11 C12 H12 120.2 . . ?
C12 C13 C8 121.4(2) . . ?
C12 C13 H13 119.3 . . ?
C8 C13 H13 119.3 . . ?
N3 C14 C15 128.1(2) . . ?
N3 C14 H14 115.9 . . ?
C15 C14 H14 115.9 . . ?
C16 C15 C14 122.8(2) . . ?
C16 C15 C24 119.4(2) . . ?
C14 C15 C24 117.6(2) . . ?
O1 C16 C15 124.4(2) . . ?
O1 C16 C17 117.02(19) . . ?
C15 C16 C17 118.6(2) . . ?
C18 C17 C16 121.7(2) . . ?
C18 C17 H17 119.2 . . ?
C16 C17 H17 119.2 . . ?
C17 C18 C19 122.0(2) . . ?
C17 C18 H18 119.0 . . ?
C19 C18 H18 119.0 . . ?
C20 C19 C18 121.1(2) . . ?
C20 C19 C24 120.3(2) . . ?
C18 C19 C24 118.6(2) . . ?
C21 C20 C19 120.9(3) . . ?
C21 C20 H20 119.6 . . ?
C19 C20 H20 119.6 . . ?
C20 C21 C22 119.8(3) . . ?
C20 C21 H21 120.1 . . ?
C22 C21 H21 120.1 . . ?
C23 C22 C21 120.6(3) . . ?
C23 C22 H22 119.7 . . ?
C21 C22 H22 119.7 . . ?
C22 C23 C24 121.6(3) . . ?
C22 C23 H23 119.2 . . ?
C24 C23 H23 119.2 . . ?
C23 C24 C19 116.7(2) . . ?
C23 C24 C15 123.8(2) . . ?
C19 C24 C15 119.5(2) . . ?
O3 C25 O2 122.7(2) . . ?
O3 C25 C26 121.1(2) . . ?
O2 C25 C26 116.2(2) . . ?
C25 C26 H26A 109.5 . . ?
C25 C26 H26B 109.5 . . ?
H26A C26 H26B 109.5 . . ?
C25 C26 H26C 109.5 . . ?
H26A C26 H26C 109.5 . . ?
H26B C26 H26C 109.5 . . ?
C7 N1 C1 105.51(19) . . ?
C7 N1 Zn1 121.29(16) . . ?
C1 N1 Zn1 133.18(15) . . ?
C7 N2 C6 107.75(19) . . ?
C7 N2 H2A 126.1 . . ?
C6 N2 H2A 126.1 . . ?
C14 N3 C9 117.93(19) . . ?
C14 N3 Zn1 124.89(16) . . ?
C9 N3 Zn1 117.17(15) . . ?
C16 O1 Zn1 130.75(14) . . ?
C16 O1 Zn1 126.81(13) . 3_756 ?
Zn1 O1 Zn1 102.45(6) . 3_756 ?
C25 O2 Zn1 117.92(15) . . ?
O2 Zn1 O1 108.63(7) . . ?
O2 Zn1 N1 130.24(7) . . ?
O1 Zn1 N1 121.09(7) . . ?
O2 Zn1 N3 98.53(7) . . ?
O1 Zn1 N3 88.05(7) . . ?
N1 Zn1 N3 85.73(7) . . ?
O2 Zn1 O1 90.24(6) . 3_756 ?
O1 Zn1 O1 77.55(6) . 3_756 ?
N1 Zn1 O1 97.94(7) . 3_756 ?
N3 Zn1 O1 164.97(7) . 3_756 ?

_diffrn_measured_fraction_theta_max 0.987
_diffrn_reflns_theta_full        27.55
_diffrn_measured_fraction_theta_full 0.987
_refine_diff_density_max         0.484
_refine_diff_density_min         -0.342
_refine_diff_density_rms         0.062
_database_code_depnum_ccdc_archive 'CCDC 978560'
#######################################################################
#
#                 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_2

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C24 H18 Cl Cu N3 O2'
_chemical_formula_weight         479.40

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           Orthorhombic
_symmetry_space_group_name_H-M   Pbca

loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'-x, y+1/2, -z+1/2'
'x+1/2, -y+1/2, -z'
'-x, -y, -z'
'x-1/2, y, -z-1/2'
'x, -y-1/2, z-1/2'
'-x-1/2, y-1/2, z'

_cell_length_a                   14.821(3)
_cell_length_b                   10.615(2)
_cell_length_c                   25.757(6)
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_volume                     4052.2(15)
_cell_formula_units_Z            8
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    6037
_cell_measurement_theta_min      2.49
_cell_measurement_theta_max      27.16

_exptl_crystal_description       block
_exptl_crystal_colour            'dark red'
_exptl_crystal_size_max          0.19
_exptl_crystal_size_mid          0.08
_exptl_crystal_size_min          0.05
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.572
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1960
_exptl_absorpt_coefficient_mu    1.238
_exptl_absorpt_correction_type   Multi-scan
_exptl_absorpt_correction_T_min  0.7988
_exptl_absorpt_correction_T_max  0.9407
_exptl_absorpt_process_details   SADABS

_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  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            26284
_diffrn_reflns_av_R_equivalents  0.0464
_diffrn_reflns_av_sigmaI/netI    0.0328
_diffrn_reflns_limit_h_min       -19
_diffrn_reflns_limit_h_max       19
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_l_min       -33
_diffrn_reflns_limit_l_max       25
_diffrn_reflns_theta_min         1.58
_diffrn_reflns_theta_max         27.54
_reflns_number_total             4655
_reflns_number_gt                3647
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'Bruker SMART'
_computing_cell_refinement       'Bruker SMART'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'

_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)+(0.0391P)²+1.9551P] 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         4655
_refine_ls_number_parameters     292
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0486
_refine_ls_R_factor_gt           0.0320
_refine_ls_wR_factor_ref         0.0833
_refine_ls_wR_factor_gt          0.0759
_refine_ls_goodness_of_fit_ref   1.045
_refine_ls_restrained_S_all      1.045
_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 -0.06219(14) 0.93922(19) 0.12697(8) 0.0195(4) Uani 1 1 d . . .
C2 C -0.11639(15) 0.8679(2) 0.16043(9) 0.0249(5) Uani 1 1 d . . .
H2 H -0.0985 0.7887 0.1719 0.030 Uiso 1 1 calc R . .
C3 C -0.19759(15) 0.9203(2) 0.17559(9) 0.0292(5) Uani 1 1 d . . .
H3 H -0.2351 0.8752 0.1978 0.035 Uiso 1 1 calc R . .
C4 C -0.22495(16) 1.0403(2) 0.15834(9) 0.0300(5) Uani 1 1 d . . .
H4 H -0.2805 1.0718 0.1690 0.036 Uiso 1 1 calc R . .
C5 C -0.17140(15) 1.1123(2) 0.12609(9) 0.0247(5) Uani 1 1 d . . .
H5 H -0.1891 1.1919 0.1150 0.030 Uiso 1 1 calc R . .
C6 C -0.08924(14) 1.05949(19) 0.11092(8) 0.0199(4) Uani 1 1 d . . .
C7 C 0.04289(13) 1.01320(18) 0.07563(8) 0.0171(4) Uani 1 1 d . . .
C8 C 0.12308(13) 1.02463(18) 0.04281(8) 0.0171(4) Uani 1 1 d . . .
C9 C 0.12435(15) 1.11703(18) 0.00387(8) 0.0205(4) Uani 1 1 d . . .
H9 H 0.0743 1.1688 -0.0004 0.025 Uiso 1 1 calc R . .
C10 C 0.19784(15) 1.13310(19) -0.02827(9) 0.0236(5) Uani 1 1 d . . .
H10 H 0.1980 1.1966 -0.0531 0.028 Uiso 1 1 calc R . .
C11 C 0.27159(15) 1.0535(2) -0.02317(9) 0.0251(5) Uani 1 1 d . . .
H11 H 0.3209 1.0625 -0.0452 0.030 Uiso 1 1 calc R . .
C12 C 0.27173(14) 0.9608(2) 0.01468(8) 0.0222(4) Uani 1 1 d . . .
H12 H 0.3212 0.9073 0.0175 0.027 Uiso 1 1 calc R . .
C13 C 0.19882(13) 0.94619(18) 0.04867(8) 0.0173(4) Uani 1 1 d . . .
C14 C 0.27870(14) 0.83330(18) 0.11141(8) 0.0183(4) Uani 1 1 d . . .
H14 H 0.3255 0.8869 0.1019 0.022 Uiso 1 1 calc R . .
C15 C 0.29953(14) 0.74030(18) 0.14958(8) 0.0179(4) Uani 1 1 d . . .
C16 C 0.23759(14) 0.64347(18) 0.16204(8) 0.0193(4) Uani 1 1 d . . .
C17 C 0.26523(15) 0.54683(19) 0.19764(8) 0.0232(5) Uani 1 1 d . . .
H17 H 0.2250 0.4828 0.2062 0.028 Uiso 1 1 calc R . .
C18 C 0.34868(15) 0.54712(19) 0.21900(8) 0.0238(5) Uani 1 1 d . . .
H18 H 0.3650 0.4814 0.2410 0.029 Uiso 1 1 calc R . .
C19 C 0.41247(14) 0.64465(19) 0.20900(8) 0.0210(4) Uani 1 1 d . . .
C20 C 0.49798(15) 0.6450(2) 0.23328(9) 0.0253(5) Uani 1 1 d . . .
H20 H 0.5131 0.5803 0.2561 0.030 Uiso 1 1 calc R . .
C21 C 0.55880(15) 0.7389(2) 0.22377(9) 0.0266(5) Uani 1 1 d . . .
H21 H 0.6150 0.7382 0.2398 0.032 Uiso 1 1 calc R . .
C22 C 0.53532(15) 0.8366(2) 0.18946(9) 0.0247(5) Uani 1 1 d . . .
H22 H 0.5769 0.8999 0.1824 0.030 Uiso 1 1 calc R . .
C23 C 0.45190(14) 0.84012(19) 0.16624(8) 0.0203(4) Uani 1 1 d . . .
H23 H 0.4373 0.9074 0.1447 0.024 Uiso 1 1 calc R . .
C24 C 0.38795(13) 0.74348(18) 0.17443(8) 0.0177(4) Uani 1 1 d . . .
Cl1 Cl -0.02263(4) 0.62549(5) 0.08502(2) 0.02447(13) Uani 1 1 d . . .
Cu1 Cu 0.092483(16) 0.75930(2) 0.107593(10) 0.01781(8) Uani 1 1 d . . .
N1 N -0.02157(12) 1.10347(17) 0.07900(7) 0.0191(4) Uani 1 1 d . . .
H1A H -0.0152(17) 1.174(3) 0.0683(10) 0.032(7) Uiso 1 1 d . . .
N2 N 0.02055(11) 0.91208(16) 0.10385(7) 0.0181(4) Uani 1 1 d . . .
N3 N 0.20147(11) 0.85169(15) 0.08824(7) 0.0176(4) Uani 1 1 d . . .
O1 O 0.15660(10) 0.63294(13) 0.14309(6) 0.0237(3) Uani 1 1 d . . .
O2 O 0.99249(13) 0.34836(16) 0.03874(8) 0.0349(4) Uani 1 1 d . . .
H2A H 0.990(2) 0.363(3) 0.0058(14) 0.054(10) Uiso 1 1 d . . .
H2B H 0.993(2) 0.411(3) 0.0529(12) 0.048(10) 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 1.393(3) . ?
C1 C2 1.400(3) . ?
C1 C6 1.401(3) . ?
C2 C3 1.382(3) . ?
C2 H2 0.9300 . ?
C3 C4 1.408(3) . ?
C3 H3 0.9300 . ?
C4 C5 1.380(3) . ?
C4 H4 0.9300 . ?
C5 C6 1.396(3) . ?
C5 H5 0.9300 . ?
C6 N1 1.378(3) . ?
C7 N2 1.338(3) . ?
C7 N1 1.356(3) . ?
C7 C8 1.464(3) . ?
C8 C9 1.403(3) . ?
C8 C13 1.406(3) . ?
C9 C10 1.379(3) . ?
C9 H9 0.9300 . ?
C10 C11 1.388(3) . ?
C10 H10 0.9300 . ?
C11 C12 1.386(3) . ?
C11 H11 0.9300 . ?
C12 C13 1.399(3) . ?
C12 H12 0.9300 . ?
C13 N3 1.431(2) . ?
C14 N3 1.306(3) . ?
C14 C15 1.427(3) . ?
C14 H14 0.9300 . ?
C15 C16 1.415(3) . ?
C15 C24 1.459(3) . ?
C16 O1 1.301(3) . ?
C16 C17 1.436(3) . ?
C17 C18 1.354(3) . ?
C17 H17 0.9300 . ?
C18 C19 1.425(3) . ?
C18 H18 0.9300 . ?
C19 C20 1.413(3) . ?
C19 C24 1.423(3) . ?
C20 C21 1.366(3) . ?
C20 H20 0.9300 . ?
C21 C22 1.407(3) . ?
C21 H21 0.9300 . ?
C22 C23 1.374(3) . ?
C22 H22 0.9300 . ?
C23 C24 1.412(3) . ?
C23 H23 0.9300 . ?
Cl1 Cu1 2.2949(6) . ?
Cu1 O1 1.8809(14) . ?
Cu1 N2 1.9432(17) . ?
Cu1 N3 1.9543(17) . ?
N1 H1A 0.80(3) . ?
O2 H2A 0.86(4) . ?
O2 H2B 0.76(3) . ?

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 131.0(2) . . ?
N2 C1 C6 108.32(18) . . ?
C2 C1 C6 120.7(2) . . ?
C3 C2 C1 117.1(2) . . ?
C3 C2 H2 121.4 . . ?
C1 C2 H2 121.4 . . ?
C2 C3 C4 121.7(2) . . ?
C2 C3 H3 119.1 . . ?
C4 C3 H3 119.1 . . ?
C5 C4 C3 121.7(2) . . ?
C5 C4 H4 119.2 . . ?
C3 C4 H4 119.2 . . ?
C4 C5 C6 116.6(2) . . ?
C4 C5 H5 121.7 . . ?
C6 C5 H5 121.7 . . ?
N1 C6 C5 131.7(2) . . ?
N1 C6 C1 106.05(18) . . ?
C5 C6 C1 122.2(2) . . ?
N2 C7 N1 110.97(18) . . ?
N2 C7 C8 125.54(17) . . ?
N1 C7 C8 123.41(18) . . ?
C9 C8 C13 118.70(19) . . ?
C9 C8 C7 118.80(18) . . ?
C13 C8 C7 122.50(18) . . ?
C10 C9 C8 121.8(2) . . ?
C10 C9 H9 119.1 . . ?
C8 C9 H9 119.1 . . ?
C9 C10 C11 119.4(2) . . ?
C9 C10 H10 120.3 . . ?
C11 C10 H10 120.3 . . ?
C12 C11 C10 120.0(2) . . ?
C12 C11 H11 120.0 . . ?
C10 C11 H11 120.0 . . ?
C11 C12 C13 121.2(2) . . ?
C11 C12 H12 119.4 . . ?
C13 C12 H12 119.4 . . ?
C12 C13 C8 118.93(18) . . ?
C12 C13 N3 120.15(18) . . ?
C8 C13 N3 120.92(18) . . ?
N3 C14 C15 127.44(19) . . ?
N3 C14 H14 116.3 . . ?
C15 C14 H14 116.3 . . ?
C16 C15 C14 121.23(19) . . ?
C16 C15 C24 120.01(18) . . ?
C14 C15 C24 118.72(18) . . ?
O1 C16 C15 125.17(19) . . ?
O1 C16 C17 116.21(18) . . ?
C15 C16 C17 118.61(19) . . ?
C18 C17 C16 121.2(2) . . ?
C18 C17 H17 119.4 . . ?
C16 C17 H17 119.4 . . ?
C17 C18 C19 122.29(19) . . ?
C17 C18 H18 118.9 . . ?
C19 C18 H18 118.9 . . ?
C20 C19 C24 120.26(19) . . ?
C20 C19 C18 121.11(19) . . ?
C24 C19 C18 118.63(19) . . ?
C21 C20 C19 120.9(2) . . ?
C21 C20 H20 119.5 . . ?
C19 C20 H20 119.5 . . ?
C20 C21 C22 119.2(2) . . ?
C20 C21 H21 120.4 . . ?
C22 C21 H21 120.4 . . ?
C23 C22 C21 121.1(2) . . ?
C23 C22 H22 119.5 . . ?
C21 C22 H22 119.5 . . ?
C22 C23 C24 121.3(2) . . ?
C22 C23 H23 119.4 . . ?
C24 C23 H23 119.4 . . ?
C23 C24 C19 117.22(19) . . ?
C23 C24 C15 123.65(18) . . ?
C19 C24 C15 119.13(18) . . ?
O1 Cu1 N2 153.69(7) . . ?
O1 Cu1 N3 93.68(7) . . ?
N2 Cu1 N3 91.26(7) . . ?
O1 Cu1 Cl1 93.29(5) . . ?
N2 Cu1 Cl1 95.52(5) . . ?
N3 Cu1 Cl1 149.37(5) . . ?
C7 N1 C6 108.15(18) . . ?
C7 N1 H1A 123.6(19) . . ?
C6 N1 H1A 127.3(19) . . ?
C7 N2 C1 106.50(17) . . ?
C7 N2 Cu1 124.10(14) . . ?
C1 N2 Cu1 129.36(14) . . ?
C14 N3 C13 117.03(17) . . ?
C14 N3 Cu1 122.22(14) . . ?
C13 N3 Cu1 120.72(13) . . ?
C16 O1 Cu1 125.97(13) . . ?
H2A O2 H2B 108(3) . . ?

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 -177.9(2) . . . . ?
C6 C1 C2 C3 1.4(3) . . . . ?
C1 C2 C3 C4 -0.1(3) . . . . ?
C2 C3 C4 C5 -1.0(4) . . . . ?
C3 C4 C5 C6 0.8(3) . . . . ?
C4 C5 C6 N1 178.8(2) . . . . ?
C4 C5 C6 C1 0.6(3) . . . . ?
N2 C1 C6 N1 -0.9(2) . . . . ?
C2 C1 C6 N1 179.66(19) . . . . ?
N2 C1 C6 C5 177.75(19) . . . . ?
C2 C1 C6 C5 -1.7(3) . . . . ?
N2 C7 C8 C9 160.59(19) . . . . ?
N1 C7 C8 C9 -15.7(3) . . . . ?
N2 C7 C8 C13 -19.2(3) . . . . ?
N1 C7 C8 C13 164.53(19) . . . . ?
C13 C8 C9 C10 -0.5(3) . . . . ?
C7 C8 C9 C10 179.78(19) . . . . ?
C8 C9 C10 C11 2.0(3) . . . . ?
C9 C10 C11 C12 -1.4(3) . . . . ?
C10 C11 C12 C13 -0.7(3) . . . . ?
C11 C12 C13 C8 2.3(3) . . . . ?
C11 C12 C13 N3 -178.50(19) . . . . ?
C9 C8 C13 C12 -1.6(3) . . . . ?
C7 C8 C13 C12 178.11(19) . . . . ?
C9 C8 C13 N3 179.11(18) . . . . ?
C7 C8 C13 N3 -1.1(3) . . . . ?
N3 C14 C15 C16 8.3(3) . . . . ?
N3 C14 C15 C24 -174.05(19) . . . . ?
C14 C15 C16 O1 -3.9(3) . . . . ?
C24 C15 C16 O1 178.56(19) . . . . ?
C14 C15 C16 C17 175.00(19) . . . . ?
C24 C15 C16 C17 -2.6(3) . . . . ?
O1 C16 C17 C18 178.8(2) . . . . ?
C15 C16 C17 C18 -0.2(3) . . . . ?
C16 C17 C18 C19 2.2(3) . . . . ?
C17 C18 C19 C20 177.7(2) . . . . ?
C17 C18 C19 C24 -1.4(3) . . . . ?
C24 C19 C20 C21 -0.6(3) . . . . ?
C18 C19 C20 C21 -179.7(2) . . . . ?
C19 C20 C21 C22 0.3(3) . . . . ?
C20 C21 C22 C23 1.2(3) . . . . ?
C21 C22 C23 C24 -2.4(3) . . . . ?
C22 C23 C24 C19 2.0(3) . . . . ?
C22 C23 C24 C15 -178.0(2) . . . . ?
C20 C19 C24 C23 -0.5(3) . . . . ?
C18 C19 C24 C23 178.63(19) . . . . ?
C20 C19 C24 C15 179.52(19) . . . . ?
C18 C19 C24 C15 -1.3(3) . . . . ?
C16 C15 C24 C23 -176.65(19) . . . . ?
C14 C15 C24 C23 5.7(3) . . . . ?
C16 C15 C24 C19 3.3(3) . . . . ?
C14 C15 C24 C19 -174.31(19) . . . . ?
N2 C7 N1 C6 0.0(2) . . . . ?
C8 C7 N1 C6 176.81(18) . . . . ?
C5 C6 N1 C7 -177.9(2) . . . . ?
C1 C6 N1 C7 0.5(2) . . . . ?
N1 C7 N2 C1 -0.6(2) . . . . ?
C8 C7 N2 C1 -177.28(19) . . . . ?
N1 C7 N2 Cu1 177.72(13) . . . . ?
C8 C7 N2 Cu1 1.0(3) . . . . ?
C2 C1 N2 C7 -179.7(2) . . . . ?
C6 C1 N2 C7 0.9(2) . . . . ?
C2 C1 N2 Cu1 2.1(3) . . . . ?
C6 C1 N2 Cu1 -177.27(14) . . . . ?
O1 Cu1 N2 C7 124.62(18) . . . . ?
N3 Cu1 N2 C7 23.70(17) . . . . ?
Cl1 Cu1 N2 C7 -126.39(16) . . . . ?
O1 Cu1 N2 C1 -57.5(3) . . . . ?
N3 Cu1 N2 C1 -158.41(18) . . . . ?
Cl1 Cu1 N2 C1 51.50(18) . . . . ?
C15 C14 N3 C13 -176.04(19) . . . . ?
C15 C14 N3 Cu1 5.9(3) . . . . ?
C12 C13 N3 C14 38.5(3) . . . . ?
C8 C13 N3 C14 -142.3(2) . . . . ?
C12 C13 N3 Cu1 -143.40(16) . . . . ?
C8 C13 N3 Cu1 35.8(2) . . . . ?
O1 Cu1 N3 C14 -17.33(17) . . . . ?
N2 Cu1 N3 C14 136.82(16) . . . . ?
Cl1 Cu1 N3 C14 -120.12(15) . . . . ?
O1 Cu1 N3 C13 164.67(15) . . . . ?
N2 Cu1 N3 C13 -41.18(15) . . . . ?
Cl1 Cu1 N3 C13 61.88(19) . . . . ?
C15 C16 O1 Cu1 -15.0(3) . . . . ?
C17 C16 O1 Cu1 166.07(14) . . . . ?
N2 Cu1 O1 C16 -78.2(2) . . . . ?
N3 Cu1 O1 C16 22.16(18) . . . . ?
Cl1 Cu1 O1 C16 172.32(17) . . . . ?

_diffrn_measured_fraction_theta_max 0.996
_diffrn_reflns_theta_full        27.54
_diffrn_measured_fraction_theta_full 0.996
_refine_diff_density_max         0.505
_refine_diff_density_min         -0.399
_refine_diff_density_rms         0.066
_database_code_depnum_ccdc_archive 'CCDC 978561'
