Supplementary Material (ESI) for Dalton Transactions
This journal is (c) The Royal Society of Chemistry 2007

data_global
_journal_name_full               'Dalton Trans.'

_journal_coden_Cambridge         0222

_publ_contact_author_name        'Steve Archibald'
_publ_contact_author_address     
;
Department of Chemistry
University of Hull
Cottingham Road
Kingston upon Hull
HU16 7RX
UNITED KINGDOM
;

_publ_contact_author_email       S.J.ARCHIBALD@HULL.AC.UK

_publ_section_title              
;
Probing key coordination interactions:
configurationally restricted metal activated CXCR4 antagonists
;
loop_
_publ_author_name
'Steve Archibald'
'Adam Bridgeman'
'Erik De Clercq'
'Christopher J. Empson'
'Steven Fiddy'
'Abid Khan'
;
G.McRobbie
;
'Christophe Pannecouque'
'Jon D. Silversides'
'Gina C. Valks'
'Nigel A. Young'

data_sja12_04
_database_code_depnum_ccdc_archive 'CCDC 644161'

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
?
;
_chemical_formula_moiety         'C19 H32 Cl Cu N4 O4, Cl O4, C0.5 H2 O0.5'
_chemical_formula_sum            'C19.50 H34 Cl2 Cu N4 O8.50'
_chemical_formula_weight         594.95

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'
N N 0.0061 0.0033 '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'
Cl Cl 0.1484 0.1585 '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'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_symmetry_cell_setting           Monoclinic
_symmetry_space_group_name_H-M   P21/c

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                   10.7155(8)
_cell_length_b                   11.8759(8)
_cell_length_c                   19.7818(15)
_cell_angle_alpha                90.00
_cell_angle_beta                 94.679(6)
_cell_angle_gamma                90.00
_cell_volume                     2509.0(3)
_cell_formula_units_Z            4
_cell_measurement_temperature    150(2)
_cell_measurement_reflns_used    155
_cell_measurement_theta_min      5.77
_cell_measurement_theta_max      61.82

_exptl_crystal_description       block
_exptl_crystal_colour            purple
_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.1
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.575
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1240
_exptl_absorpt_coefficient_mu    1.138
_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      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  'Stoe IPDS-II image plate'
_diffrn_measurement_method       
'\w scans, 140 frames at 1\% intervals, exposure time 3 minutes'
_diffrn_reflns_number            27375
_diffrn_reflns_av_R_equivalents  0.0403
_diffrn_reflns_av_sigmaI/netI    0.0510
_diffrn_reflns_limit_h_min       -17
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_k_min       -19
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_l_min       -31
_diffrn_reflns_limit_l_max       30
_diffrn_reflns_theta_min         2.69
_diffrn_reflns_theta_max         34.86
_reflns_number_total             9987
_reflns_number_gt                6096
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'X-AREA (Stoe & Cie, 2002)'
_computing_cell_refinement       'X-AREA (Stoe & Cie, 2002)'
_computing_data_reduction        'X-RED (Stoe & Cie, 2002)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 1997)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 1997)'
_computing_molecular_graphics    'ORTEP III (Farrugia, 1997)'
_computing_publication_material  
'SHELXL97(Sheldrick, 1997) and WinGX (Farrugia, 1999)'

_refine_special_details          
;
Refinement of F^2^ against ALL reflections. The weighted R-factor wR and
goodness of fit S are based on F^2^, conventional R-factors R are based
on F, with F set to zero for negative F^2^. The threshold expression of
F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is
not relevant to the choice of reflections for refinement. R-factors based
on F^2^ are statistically about twice as large as those based on F, and R-
factors based on ALL data will be even larger.
;

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[\s^2^(Fo^2^)+(0.1139P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     SHELXL
_refine_ls_extinction_coef       0.0305(19)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^
_refine_ls_number_reflns         9987
_refine_ls_number_parameters     326
_refine_ls_number_restraints     2
_refine_ls_R_factor_all          0.0945
_refine_ls_R_factor_gt           0.0593
_refine_ls_wR_factor_ref         0.1795
_refine_ls_wR_factor_gt          0.1532
_refine_ls_goodness_of_fit_ref   0.977
_refine_ls_restrained_S_all      0.989
_refine_ls_shift/su_max          0.019
_refine_ls_shift/su_mean         0.002

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 0.0900(3) 0.7651(3) 0.09907(18) 0.0435(7) Uani 1 1 d . . .
H1A H 0.0355 0.8196 0.0750 0.052 Uiso 1 1 calc R . .
H1B H 0.0447 0.6945 0.1001 0.052 Uiso 1 1 calc R . .
C2 C 0.2050(3) 0.7480(3) 0.06035(16) 0.0407(7) Uani 1 1 d . . .
H2A H 0.1791 0.7124 0.0173 0.049 Uiso 1 1 calc R . .
H2B H 0.2609 0.6963 0.0858 0.049 Uiso 1 1 calc R . .
C3 C 0.2779(3) 0.8544(3) 0.04628(14) 0.0362(6) Uani 1 1 d . . .
H3A H 0.3367 0.8374 0.0129 0.043 Uiso 1 1 calc R . .
H3B H 0.2199 0.9106 0.0268 0.043 Uiso 1 1 calc R . .
C4 C 0.3985(3) 1.0168(2) 0.09249(15) 0.0344(6) Uani 1 1 d . . .
H4A H 0.3362 1.0584 0.0643 0.041 Uiso 1 1 calc R . .
H4B H 0.4722 1.0085 0.0675 0.041 Uiso 1 1 calc R . .
C5 C 0.4326(3) 1.0819(2) 0.15752(16) 0.0344(6) Uani 1 1 d . . .
H5A H 0.5051 1.0481 0.1822 0.041 Uiso 1 1 calc R . .
H5B H 0.4528 1.1592 0.1470 0.041 Uiso 1 1 calc R . .
C6 C 0.3559(3) 1.1146(2) 0.27116(15) 0.0341(6) Uani 1 1 d . . .
H6A H 0.3731 1.1947 0.2722 0.041 Uiso 1 1 calc R . .
H6B H 0.4312 1.0757 0.2889 0.041 Uiso 1 1 calc R . .
C7 C 0.2507(3) 1.0893(2) 0.31590(15) 0.0355(6) Uani 1 1 d . . .
H7A H 0.1721 1.1132 0.2925 0.043 Uiso 1 1 calc R . .
H7B H 0.2636 1.1336 0.3571 0.043 Uiso 1 1 calc R . .
C8 C 0.2400(3) 0.9656(3) 0.33516(15) 0.0352(6) Uani 1 1 d . . .
H8A H 0.3223 0.9369 0.3503 0.042 Uiso 1 1 calc R . .
H8B H 0.1870 0.9587 0.3724 0.042 Uiso 1 1 calc R . .
C9 C 0.2294(3) 0.7776(2) 0.28173(16) 0.0361(6) Uani 1 1 d . . .
H9A H 0.1995 0.7421 0.3215 0.043 Uiso 1 1 calc R . .
H9B H 0.3202 0.7741 0.2853 0.043 Uiso 1 1 calc R . .
C10 C 0.1756(3) 0.7169(2) 0.21681(18) 0.0385(6) Uani 1 1 d . . .
H10A H 0.2414 0.6770 0.1959 0.046 Uiso 1 1 calc R . .
H10B H 0.1120 0.6631 0.2275 0.046 Uiso 1 1 calc R . .
C11 C 0.0058(3) 0.8468(2) 0.20044(17) 0.0369(6) Uani 1 1 d . . .
H11A H -0.0519 0.7852 0.2059 0.044 Uiso 1 1 calc R . .
H11B H -0.0362 0.9030 0.1712 0.044 Uiso 1 1 calc R . .
C12 C 0.0476(3) 0.8985(2) 0.26962(16) 0.0337(5) Uani 1 1 d . . .
H12A H 0.0168 0.9751 0.2721 0.040 Uiso 1 1 calc R . .
H12B H 0.0148 0.8549 0.3057 0.040 Uiso 1 1 calc R . .
C13 C 0.4512(3) 0.8254(2) 0.13627(13) 0.0286(5) Uani 1 1 d . . .
H13A H 0.4938 0.8613 0.1757 0.034 Uiso 1 1 calc R . .
H13B H 0.4128 0.7571 0.1517 0.034 Uiso 1 1 calc R . .
C14 C 0.5476(3) 0.7931(2) 0.08860(13) 0.0292(5) Uani 1 1 d . . .
C15 C 0.6585(3) 0.8553(2) 0.08727(14) 0.0328(5) Uani 1 1 d . . .
H15 H 0.6722 0.9171 0.1157 0.039 Uiso 1 1 calc R . .
C16 C 0.7483(3) 0.8249(3) 0.04353(16) 0.0369(6) Uani 1 1 d . . .
H16 H 0.8216 0.8667 0.0429 0.044 Uiso 1 1 calc R . .
C17 C 0.7288(3) 0.7328(3) 0.00094(16) 0.0410(7) Uani 1 1 d . . .
H17 H 0.7884 0.7133 -0.0286 0.049 Uiso 1 1 calc R . .
C18 C 0.6209(3) 0.6702(3) 0.00252(16) 0.0411(7) Uani 1 1 d . . .
H18 H 0.6082 0.6080 -0.0258 0.049 Uiso 1 1 calc R . .
C19 C 0.5306(3) 0.6994(2) 0.04629(15) 0.0354(6) Uani 1 1 d . . .
H19 H 0.4584 0.6561 0.0473 0.042 Uiso 1 1 calc R . .
C20 C 0.0000 0.5000 0.0000 0.136(6) Uani 1 2 d SD . .
N1 N 0.1200(2) 0.8050(2) 0.17009(13) 0.0332(5) Uani 1 1 d . . .
N2 N 0.3482(2) 0.90315(19) 0.10769(11) 0.0284(4) Uani 1 1 d . . .
N3 N 0.3231(2) 1.07849(18) 0.19946(12) 0.0291(4) Uani 1 1 d D . .
H20 H 0.267(3) 1.129(2) 0.1858(18) 0.035 Uiso 1 1 d D . .
N4 N 0.1866(2) 0.89757(19) 0.27692(12) 0.0298(4) Uani 1 1 d . . .
Cu1 Cu 0.23799(3) 0.93308(2) 0.183644(16) 0.02584(10) Uani 1 1 d . . .
Cl1 Cl 0.00248(6) 1.11924(6) 0.10902(3) 0.03338(15) Uani 1 1 d . . .
Cl2 Cl 0.66593(7) 0.91956(5) 0.31270(4) 0.03509(15) Uani 1 1 d . . .
O1 O 0.0367(2) 1.1418(2) 0.18004(13) 0.0464(5) Uani 1 1 d . . .
O2 O -0.1194(3) 1.0706(2) 0.10229(16) 0.0520(6) Uani 1 1 d . . .
O3 O 0.0956(3) 1.0421(3) 0.08802(17) 0.0655(9) Uani 1 1 d . . .
O4 O 0.0029(3) 1.2228(3) 0.07305(15) 0.0607(8) Uani 1 1 d . . .
O5 O 0.5431(2) 0.8701(2) 0.30243(14) 0.0479(6) Uani 1 1 d . . .
O6 O 0.6989(3) 0.9671(3) 0.25031(13) 0.0565(7) Uani 1 1 d . . .
O7 O 0.6649(3) 1.0063(2) 0.36276(14) 0.0633(8) Uani 1 1 d . . .
O8 O 0.7528(3) 0.8337(3) 0.33463(18) 0.0646(8) Uani 1 1 d . . .
O9 O 0.0333(6) 0.4952(5) 0.0799(3) 0.0639(15) Uani 0.50 1 d PD . .

loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_23
_atom_site_aniso_U_13
_atom_site_aniso_U_12
C1 0.0339(14) 0.0478(16) 0.0475(17) -0.0189(13) -0.0046(13) -0.0012(12)
C2 0.0370(15) 0.0471(15) 0.0368(14) -0.0154(12) -0.0033(13) 0.0029(12)
C3 0.0337(14) 0.0472(15) 0.0272(12) -0.0042(10) -0.0011(11) 0.0112(11)
C4 0.0378(14) 0.0337(12) 0.0328(12) 0.0085(9) 0.0093(12) 0.0076(10)
C5 0.0335(13) 0.0287(11) 0.0419(14) 0.0046(9) 0.0086(12) -0.0006(9)
C6 0.0361(14) 0.0296(11) 0.0362(13) -0.0036(9) 0.0009(12) -0.0034(9)
C7 0.0377(14) 0.0344(12) 0.0343(13) -0.0099(10) 0.0018(12) 0.0016(10)
C8 0.0380(14) 0.0407(13) 0.0272(11) -0.0016(10) 0.0046(11) -0.0007(11)
C9 0.0334(13) 0.0313(12) 0.0440(15) 0.0060(10) 0.0067(12) 0.0027(10)
C10 0.0368(14) 0.0278(11) 0.0520(17) -0.0014(11) 0.0099(13) -0.0016(10)
C11 0.0283(12) 0.0337(12) 0.0489(16) -0.0047(11) 0.0039(12) -0.0020(9)
C12 0.0296(13) 0.0338(12) 0.0391(14) 0.0015(10) 0.0121(12) -0.0002(9)
C13 0.0304(12) 0.0285(10) 0.0270(11) 0.0018(8) 0.0027(10) 0.0029(9)
C14 0.0292(12) 0.0320(11) 0.0266(10) 0.0024(8) 0.0029(10) 0.0060(9)
C15 0.0328(13) 0.0343(12) 0.0312(12) 0.0043(9) 0.0013(11) 0.0028(9)
C16 0.0292(13) 0.0462(15) 0.0363(13) 0.0119(11) 0.0080(11) 0.0071(11)
C17 0.0386(15) 0.0513(17) 0.0344(13) 0.0059(12) 0.0119(13) 0.0138(13)
C18 0.0455(17) 0.0425(15) 0.0363(14) -0.0048(11) 0.0083(13) 0.0091(12)
C19 0.0358(14) 0.0373(13) 0.0337(13) -0.0037(10) 0.0072(12) 0.0030(10)
C20 0.239(15) 0.048(4) 0.138(9) -0.019(5) 0.122(10) -0.022(6)
N1 0.0272(10) 0.0335(10) 0.0394(12) -0.0068(9) 0.0051(10) -0.0010(8)
N2 0.0292(10) 0.0314(9) 0.0248(9) -0.0003(7) 0.0045(9) 0.0056(8)
N3 0.0287(10) 0.0264(9) 0.0323(10) 0.0011(7) 0.0035(9) 0.0019(7)
N4 0.0301(11) 0.0302(9) 0.0298(10) 0.0005(8) 0.0067(9) 0.0013(8)
Cu1 0.02590(16) 0.02579(14) 0.02614(15) -0.00166(10) 0.00404(11) -0.00043(10)
Cl1 0.0305(3) 0.0368(3) 0.0332(3) 0.0014(2) 0.0043(3) 0.0056(2)
Cl2 0.0396(4) 0.0324(3) 0.0328(3) 0.0019(2) 0.0002(3) -0.0021(2)
O1 0.0439(13) 0.0553(14) 0.0394(11) -0.0029(10) 0.0003(10) 0.0030(10)
O2 0.0387(12) 0.0496(13) 0.0656(17) -0.0014(11) -0.0075(12) -0.0042(10)
O3 0.0583(18) 0.080(2) 0.0592(17) -0.0165(15) 0.0091(15) 0.0275(15)
O4 0.0485(15) 0.0695(17) 0.0633(17) 0.0317(14) -0.0003(14) 0.0010(13)
O5 0.0423(13) 0.0434(12) 0.0575(14) -0.0032(10) 0.0016(12) -0.0025(9)
O6 0.0650(18) 0.0674(17) 0.0372(12) 0.0051(11) 0.0043(12) -0.0127(14)
O7 0.100(2) 0.0455(13) 0.0459(14) -0.0090(11) 0.0134(15) -0.0245(15)
O8 0.0497(15) 0.0596(17) 0.082(2) 0.0180(15) -0.0100(15) 0.0085(12)
O9 0.070(4) 0.056(3) 0.069(4) 0.007(3) 0.020(3) 0.012(3)

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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
C1 N1 1.493(4) . ?
C1 C2 1.516(5) . ?
C2 C3 1.524(5) . ?
C3 N2 1.493(3) . ?
C4 N2 1.493(4) . ?
C4 C5 1.519(4) . ?
C5 N3 1.492(4) . ?
C6 N3 1.496(4) . ?
C6 C7 1.519(5) . ?
C7 C8 1.525(4) . ?
C8 N4 1.483(4) . ?
C9 N4 1.497(4) . ?
C9 C10 1.543(4) . ?
C10 N1 1.487(4) . ?
C11 N1 1.492(4) . ?
C11 C12 1.533(4) . ?
C12 N4 1.485(4) . ?
C13 C14 1.504(4) . ?
C13 N2 1.512(3) . ?
C14 C19 1.395(4) . ?
C14 C15 1.401(4) . ?
C15 C16 1.393(4) . ?
C16 C17 1.386(5) . ?
C17 C18 1.377(5) . ?
C18 C19 1.394(5) . ?
C20 O9 1.592(6) . ?
C20 O9 1.592(6) 3_565 ?
N1 Cu1 1.982(2) . ?
N2 Cu1 2.017(2) . ?
N3 Cu1 1.966(2) . ?
N4 Cu1 2.013(2) . ?
Cu1 O3 2.667(3) . ?
Cl1 O4 1.421(3) . ?
Cl1 O2 1.424(3) . ?
Cl1 O3 1.441(3) . ?
Cl1 O1 1.448(2) . ?
Cl2 O8 1.424(3) . ?
Cl2 O6 1.427(3) . ?
Cl2 O7 1.430(3) . ?
Cl2 O5 1.441(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
N1 C1 C2 113.4(2) . . ?
C1 C2 C3 115.5(3) . . ?
N2 C3 C2 113.9(2) . . ?
N2 C4 C5 110.8(2) . . ?
N3 C5 C4 108.1(2) . . ?
N3 C6 C7 111.6(2) . . ?
C6 C7 C8 114.2(3) . . ?
N4 C8 C7 111.3(2) . . ?
N4 C9 C10 107.4(2) . . ?
N1 C10 C9 107.0(2) . . ?
N1 C11 C12 107.6(2) . . ?
N4 C12 C11 107.6(2) . . ?
C14 C13 N2 116.0(2) . . ?
C19 C14 C15 118.6(3) . . ?
C19 C14 C13 121.1(3) . . ?
C15 C14 C13 120.3(2) . . ?
C16 C15 C14 120.4(3) . . ?
C17 C16 C15 120.3(3) . . ?
C18 C17 C16 119.9(3) . . ?
C17 C18 C19 120.4(3) . . ?
C18 C19 C14 120.5(3) . . ?
O9 C20 O9 180.0(4) . 3_565 ?
C10 N1 C11 106.5(2) . . ?
C10 N1 C1 113.9(2) . . ?
C11 N1 C1 111.3(2) . . ?
C10 N1 Cu1 103.74(17) . . ?
C11 N1 Cu1 103.03(16) . . ?
C1 N1 Cu1 117.2(2) . . ?
C4 N2 C3 110.7(2) . . ?
C4 N2 C13 111.3(2) . . ?
C3 N2 C13 111.8(2) . . ?
C4 N2 Cu1 103.51(17) . . ?
C3 N2 Cu1 112.76(19) . . ?
C13 N2 Cu1 106.42(16) . . ?
C5 N3 C6 112.6(2) . . ?
C5 N3 Cu1 108.11(17) . . ?
C6 N3 Cu1 118.19(18) . . ?
C8 N4 C12 113.1(2) . . ?
C8 N4 C9 111.9(2) . . ?
C12 N4 C9 108.2(2) . . ?
C8 N4 Cu1 118.75(19) . . ?
C12 N4 Cu1 104.86(17) . . ?
C9 N4 Cu1 98.76(18) . . ?
N3 Cu1 N1 167.99(10) . . ?
N3 Cu1 N4 101.31(10) . . ?
N1 Cu1 N4 75.17(10) . . ?
N3 Cu1 N2 88.91(10) . . ?
N1 Cu1 N2 99.77(10) . . ?
N4 Cu1 N2 150.05(9) . . ?
N3 Cu1 O3 85.27(10) . . ?
N1 Cu1 O3 87.42(11) . . ?
N4 Cu1 O3 124.65(10) . . ?
N2 Cu1 O3 83.86(9) . . ?
O4 Cl1 O2 110.15(16) . . ?
O4 Cl1 O3 112.1(2) . . ?
O2 Cl1 O3 111.5(2) . . ?
O4 Cl1 O1 108.38(18) . . ?
O2 Cl1 O1 108.87(17) . . ?
O3 Cl1 O1 105.70(17) . . ?
O8 Cl2 O6 110.2(2) . . ?
O8 Cl2 O7 110.3(2) . . ?
O6 Cl2 O7 109.29(18) . . ?
O8 Cl2 O5 108.54(17) . . ?
O6 Cl2 O5 109.10(17) . . ?
O7 Cl2 O5 109.40(19) . . ?
Cl1 O3 Cu1 118.29(18) . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
N1 C1 C2 C3 -66.0(4) . . . . ?
C1 C2 C3 N2 71.6(3) . . . . ?
N2 C4 C5 N3 -50.9(3) . . . . ?
N3 C6 C7 C8 75.9(3) . . . . ?
C6 C7 C8 N4 -73.8(3) . . . . ?
N4 C9 C10 N1 9.1(3) . . . . ?
N1 C11 C12 N4 5.6(3) . . . . ?
N2 C13 C14 C19 -88.5(3) . . . . ?
N2 C13 C14 C15 93.3(3) . . . . ?
C19 C14 C15 C16 1.2(4) . . . . ?
C13 C14 C15 C16 179.5(2) . . . . ?
C14 C15 C16 C17 -0.1(4) . . . . ?
C15 C16 C17 C18 -0.8(4) . . . . ?
C16 C17 C18 C19 0.5(5) . . . . ?
C17 C18 C19 C14 0.7(5) . . . . ?
C15 C14 C19 C18 -1.5(4) . . . . ?
C13 C14 C19 C18 -179.8(3) . . . . ?
C9 C10 N1 C11 -70.3(3) . . . . ?
C9 C10 N1 C1 166.6(3) . . . . ?
C9 C10 N1 Cu1 38.1(3) . . . . ?
C12 C11 N1 C10 61.8(3) . . . . ?
C12 C11 N1 C1 -173.5(3) . . . . ?
C12 C11 N1 Cu1 -47.0(3) . . . . ?
C2 C1 N1 C10 -73.3(4) . . . . ?
C2 C1 N1 C11 166.3(3) . . . . ?
C2 C1 N1 Cu1 48.1(3) . . . . ?
C5 C4 N2 C3 161.8(2) . . . . ?
C5 C4 N2 C13 -73.2(3) . . . . ?
C5 C4 N2 Cu1 40.8(2) . . . . ?
C2 C3 N2 C4 -170.1(2) . . . . ?
C2 C3 N2 C13 65.2(3) . . . . ?
C2 C3 N2 Cu1 -54.7(3) . . . . ?
C14 C13 N2 C4 -66.6(3) . . . . ?
C14 C13 N2 C3 57.7(3) . . . . ?
C14 C13 N2 Cu1 -178.72(18) . . . . ?
C4 C5 N3 C6 165.8(2) . . . . ?
C4 C5 N3 Cu1 33.3(2) . . . . ?
C7 C6 N3 C5 -169.1(2) . . . . ?
C7 C6 N3 Cu1 -41.8(3) . . . . ?
C7 C8 N4 C12 -84.7(3) . . . . ?
C7 C8 N4 C9 152.8(3) . . . . ?
C7 C8 N4 Cu1 38.7(3) . . . . ?
C11 C12 N4 C8 168.5(2) . . . . ?
C11 C12 N4 C9 -67.1(3) . . . . ?
C11 C12 N4 Cu1 37.6(2) . . . . ?
C10 C9 N4 C8 -176.4(3) . . . . ?
C10 C9 N4 C12 58.3(3) . . . . ?
C10 C9 N4 Cu1 -50.6(2) . . . . ?
C5 N3 Cu1 N1 -145.6(5) . . . . ?
C6 N3 Cu1 N1 84.9(5) . . . . ?
C5 N3 Cu1 N4 142.63(17) . . . . ?
C6 N3 Cu1 N4 13.2(2) . . . . ?
C5 N3 Cu1 N2 -9.01(17) . . . . ?
C6 N3 Cu1 N2 -138.4(2) . . . . ?
C5 N3 Cu1 O3 -92.94(17) . . . . ?
C6 N3 Cu1 O3 137.6(2) . . . . ?
C10 N1 Cu1 N3 -130.0(5) . . . . ?
C11 N1 Cu1 N3 -19.1(6) . . . . ?
C1 N1 Cu1 N3 103.5(5) . . . . ?
C10 N1 Cu1 N4 -55.58(19) . . . . ?
C11 N1 Cu1 N4 55.29(18) . . . . ?
C1 N1 Cu1 N4 177.9(2) . . . . ?
C10 N1 Cu1 N2 94.17(19) . . . . ?
C11 N1 Cu1 N2 -154.95(18) . . . . ?
C1 N1 Cu1 N2 -32.4(2) . . . . ?
C10 N1 Cu1 O3 177.49(19) . . . . ?
C11 N1 Cu1 O3 -71.63(19) . . . . ?
C1 N1 Cu1 O3 51.0(2) . . . . ?
C8 N4 Cu1 N3 -12.0(2) . . . . ?
C12 N4 Cu1 N3 115.45(17) . . . . ?
C9 N4 Cu1 N3 -132.92(16) . . . . ?
C8 N4 Cu1 N1 179.8(2) . . . . ?
C12 N4 Cu1 N1 -52.76(17) . . . . ?
C9 N4 Cu1 N1 58.87(17) . . . . ?
C8 N4 Cu1 N2 96.0(3) . . . . ?
C12 N4 Cu1 N2 -136.6(2) . . . . ?
C9 N4 Cu1 N2 -25.0(3) . . . . ?
C8 N4 Cu1 O3 -104.1(2) . . . . ?
C12 N4 Cu1 O3 23.4(2) . . . . ?
C9 N4 Cu1 O3 135.00(17) . . . . ?
C4 N2 Cu1 N3 -17.33(16) . . . . ?
C3 N2 Cu1 N3 -136.97(19) . . . . ?
C13 N2 Cu1 N3 100.05(16) . . . . ?
C4 N2 Cu1 N1 154.33(16) . . . . ?
C3 N2 Cu1 N1 34.69(19) . . . . ?
C13 N2 Cu1 N1 -88.29(17) . . . . ?
C4 N2 Cu1 N4 -128.4(2) . . . . ?
C3 N2 Cu1 N4 111.9(2) . . . . ?
C13 N2 Cu1 N4 -11.1(3) . . . . ?
C4 N2 Cu1 O3 68.03(17) . . . . ?
C3 N2 Cu1 O3 -51.61(19) . . . . ?
C13 N2 Cu1 O3 -174.59(18) . . . . ?
O4 Cl1 O3 Cu1 134.5(2) . . . . ?
O2 Cl1 O3 Cu1 -101.5(2) . . . . ?
O1 Cl1 O3 Cu1 16.7(3) . . . . ?
N3 Cu1 O3 Cl1 -74.0(2) . . . . ?
N1 Cu1 O3 Cl1 96.5(2) . . . . ?
N4 Cu1 O3 Cl1 26.5(3) . . . . ?
N2 Cu1 O3 Cl1 -163.4(2) . . . . ?

_diffrn_measured_fraction_theta_max 0.914
_diffrn_reflns_theta_full        25.00
_diffrn_measured_fraction_theta_full 0.968
_refine_diff_density_max         1.182
_refine_diff_density_min         -1.001
_refine_diff_density_rms         0.157