# 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.
# 
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#  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

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C24 H29 Br Cl Cu N5 O6'
_chemical_formula_weight         662.42

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'
Br Br -0.2901 2.4595 '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'

_symmetry_cell_setting           Triclinic
_symmetry_space_group_name_H-M   P-1

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

_cell_length_a                   10.906(5)
_cell_length_b                   11.079(5)
_cell_length_c                   12.921(5)
_cell_angle_alpha                102.848(5)
_cell_angle_beta                 113.134(5)
_cell_angle_gamma                90.888(5)
_cell_volume                     1390.5(10)
_cell_formula_units_Z            2
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    5474
_cell_measurement_theta_min      2.6255
_cell_measurement_theta_max      2.616

_exptl_crystal_description       Block
_exptl_crystal_colour            Brown
_exptl_crystal_size_max          0.30
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.20
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.582
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             674
_exptl_absorpt_coefficient_mu    2.365
_exptl_absorpt_correction_type   Multi-scan
_exptl_absorpt_correction_T_min  0.5262
_exptl_absorpt_correction_T_max  0.6501
_exptl_absorpt_process_details   'SADABS(Bruker 1999)'

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      293(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Bruker axs kappa apex2 CCD Diffractometer'
_diffrn_measurement_method       'ω and φ scan'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            21174
_diffrn_reflns_av_R_equivalents  0.0502
_diffrn_reflns_av_sigmaI/netI    0.0460
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_l_min       -10
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_theta_min         2.09
_diffrn_reflns_theta_max         25.00
_reflns_number_total             4840
_reflns_number_gt                3246
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'APEX2 (Bruker, 2004)'
_computing_cell_refinement       'APEX2/SAINT (Bruker, 2004)'
_computing_data_reduction        'SAINT/XPREP (Bruker, 2004)'
_computing_structure_solution    'SIR92 (Altornare et al., 1993)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_molecular_graphics    
'ORTEP3 (Farrugia, 1997) and Mercury (Bruno et al., 2002)'
_computing_publication_material  'SHELXL-97 (Sheldrick, 2008)'


_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)+(0.0521P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         4840
_refine_ls_number_parameters     403
_refine_ls_number_restraints     87
_refine_ls_R_factor_all          0.0664
_refine_ls_R_factor_gt           0.0368
_refine_ls_wR_factor_ref         0.0976
_refine_ls_wR_factor_gt          0.0870
_refine_ls_goodness_of_fit_ref   1.007
_refine_ls_restrained_S_all      1.049
_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 0.2448(4) 0.4802(4) 0.3515(3) 0.0470(9) Uani 1 1 d . A .
C2 C 0.1633(4) 0.5602(4) 0.2922(3) 0.0577(10) Uani 1 1 d . . .
H2 H 0.1724 0.6439 0.3298 0.069 Uiso 1 1 calc R . .
C3 C 0.0700(4) 0.5180(5) 0.1798(4) 0.0679(12) Uani 1 1 d . . .
H3 H 0.0172 0.5736 0.1428 0.081 Uiso 1 1 calc R . .
C4 C 0.0532(4) 0.3947(5) 0.1207(4) 0.0728(13) Uani 1 1 d . . .
H4 H -0.0114 0.3668 0.0450 0.087 Uiso 1 1 calc R . .
C5 C 0.1321(4) 0.3150(4) 0.1747(3) 0.0656(12) Uani 1 1 d . . .
H5 H 0.1220 0.2322 0.1343 0.079 Uiso 1 1 calc R . .
C6 C 0.2288(4) 0.3532(4) 0.2896(3) 0.0477(9) Uani 1 1 d . . .
C7 C 0.3086(4) 0.2639(4) 0.3388(3) 0.0548(10) Uani 1 1 d . A .
H7 H 0.2972 0.1848 0.2905 0.066 Uiso 1 1 calc R . .
C8 C 0.4832(9) 0.1897(7) 0.4846(4) 0.0612(18) Uani 0.844(15) 1 d PDU A 1
H8A H 0.5713 0.2095 0.4867 0.073 Uiso 0.844(15) 1 calc PR A 1
H8B H 0.4461 0.1074 0.4335 0.073 Uiso 0.844(15) 1 calc PR A 1
C9 C 0.4928(10) 0.1938(5) 0.6048(5) 0.0611(18) Uani 0.844(15) 1 d PDU A 1
H9A H 0.4107 0.1537 0.6007 0.073 Uiso 0.844(15) 1 calc PR A 1
H9B H 0.5671 0.1509 0.6448 0.073 Uiso 0.844(15) 1 calc PR A 1
C8' C 0.440(3) 0.164(3) 0.498(3) 0.061(5) Uani 0.156(15) 1 d PDU A 2
H8'1 H 0.3704 0.1291 0.5152 0.073 Uiso 0.156(15) 1 calc PR A 2
H8'2 H 0.4619 0.0998 0.4457 0.073 Uiso 0.156(15) 1 calc PR A 2
C9' C 0.563(4) 0.218(3) 0.609(2) 0.061(5) Uani 0.156(15) 1 d PDU A 2
H9'1 H 0.5917 0.1582 0.6557 0.074 Uiso 0.156(15) 1 calc PR A 2
H9'2 H 0.6372 0.2446 0.5919 0.074 Uiso 0.156(15) 1 calc PR A 2
C10 C 0.5791(4) 0.3605(3) 0.7773(3) 0.0527(10) Uani 1 1 d . A .
H10 H 0.6237 0.3011 0.8144 0.063 Uiso 1 1 calc R . .
C11 C 0.5888(3) 0.4835(3) 0.8488(3) 0.0414(8) Uani 1 1 d . . .
C12 C 0.6589(4) 0.5032(4) 0.9686(3) 0.0502(9) Uani 1 1 d . . .
H12 H 0.7028 0.4398 0.9993 0.060 Uiso 1 1 calc R . .
C13 C 0.6635(4) 0.6152(4) 1.0409(3) 0.0515(10) Uani 1 1 d . . .
C14 C 0.5971(4) 0.7099(4) 0.9979(3) 0.0505(9) Uani 1 1 d . . .
H14 H 0.5985 0.7844 1.0488 0.061 Uiso 1 1 calc R . .
C15 C 0.5290(3) 0.6946(3) 0.8802(3) 0.0444(9) Uani 1 1 d . . .
C16 C 0.5257(3) 0.5808(3) 0.8021(3) 0.0413(8) Uani 1 1 d . A .
C17 C 0.4658(4) 0.8005(3) 0.8335(3) 0.0528(10) Uani 1 1 d . . .
H17A H 0.5242 0.8393 0.8067 0.063 Uiso 1 1 calc R . .
H17B H 0.4571 0.8625 0.8956 0.063 Uiso 1 1 calc R . .
C18 C 0.2305(3) 0.7021(4) 0.7659(3) 0.0514(9) Uani 1 1 d . . .
H18A H 0.2139 0.7616 0.8251 0.062 Uiso 1 1 calc R . .
H18B H 0.2649 0.6315 0.7967 0.062 Uiso 1 1 calc R . .
C19 C 0.1028(4) 0.6596(4) 0.6598(3) 0.0604(11) Uani 1 1 d . . .
H19A H 0.1194 0.5980 0.6020 0.073 Uiso 1 1 calc R . .
H19B H 0.0376 0.6205 0.6795 0.073 Uiso 1 1 calc R . .
C20 C 0.1445(4) 0.8188(4) 0.5809(3) 0.0669(12) Uani 1 1 d . . .
H20A H 0.1078 0.8877 0.5484 0.080 Uiso 1 1 calc R . .
H20B H 0.1600 0.7583 0.5217 0.080 Uiso 1 1 calc R . .
C21 C 0.2758(4) 0.8656(4) 0.6838(3) 0.0623(11) Uani 1 1 d . . .
H21A H 0.3389 0.9007 0.6595 0.075 Uiso 1 1 calc R . .
H21B H 0.2623 0.9305 0.7412 0.075 Uiso 1 1 calc R . .
C22 C -0.0785(4) 0.7205(5) 0.5096(4) 0.0913(16) Uani 1 1 d . . .
H22A H -0.1130 0.7905 0.4797 0.137 Uiso 1 1 calc R . .
H22B H -0.1421 0.6836 0.5314 0.137 Uiso 1 1 calc R . .
H22C H -0.0639 0.6600 0.4510 0.137 Uiso 1 1 calc R . .
N5 N 0.1918(8) 0.9533(7) 1.3909(6) 0.152(3) Uani 1 1 d . . .
C24 C -0.0035(7) 0.9402(8) 1.1955(7) 0.144(3) Uani 1 1 d . . .
H24A H 0.0077 1.0118 1.1684 0.215 Uiso 1 1 calc R . .
H24B H -0.0868 0.9385 1.2045 0.215 Uiso 1 1 calc R . .
H24C H -0.0043 0.8659 1.1402 0.215 Uiso 1 1 calc R . .
N1 N 0.3947(3) 0.2828(3) 0.4437(3) 0.0492(8) Uani 1 1 d . . .
N2 N 0.5142(3) 0.3268(3) 0.6673(3) 0.0502(8) Uani 1 1 d . . .
N3 N 0.0490(3) 0.7622(3) 0.6119(3) 0.0604(9) Uani 1 1 d . . .
N4 N 0.3302(3) 0.7608(3) 0.7353(3) 0.0434(7) Uani 1 1 d D . .
C25 C 0.1056(9) 0.9467(7) 1.3054(8) 0.115(2) Uani 1 1 d . . .
O1 O 0.3337(2) 0.5262(2) 0.45919(19) 0.0542(7) Uani 1 1 d . . .
O2 O 0.4593(2) 0.5728(2) 0.68988(18) 0.0435(6) Uani 1 1 d . . .
Cl1 Cl 0.70798(12) 1.07440(10) 0.92438(9) 0.0671(3) Uani 1 1 d . . .
O3 O 0.7231(12) 1.0099(12) 1.0070(11) 0.133(5) Uani 0.599(11) 1 d PU B 1
O4 O 0.7055(12) 1.0048(8) 0.8268(9) 0.127(4) Uani 0.599(11) 1 d PU B 1
O5 O 0.5712(8) 1.1076(8) 0.8926(10) 0.140(4) Uani 0.599(11) 1 d PU B 1
O6 O 0.8021(11) 1.1785(12) 0.9625(12) 0.124(5) Uani 0.599(11) 1 d PU B 1
O3' O 0.7995(16) 0.9840(12) 0.9125(16) 0.155(6) Uani 0.401(11) 1 d PU B 2
O4' O 0.6106(14) 1.0460(11) 0.8130(9) 0.111(5) Uani 0.401(11) 1 d PU B 2
O5' O 0.7542(15) 1.1981(13) 0.9653(11) 0.079(4) Uani 0.401(11) 1 d PU B 2
O6' O 0.6722(14) 1.0373(14) 1.0091(11) 0.083(5) Uani 0.401(11) 1 d PU B 2
Cu1 Cu 0.43001(4) 0.43167(4) 0.56457(3) 0.04124(15) Uani 1 1 d . A .
Br1 Br 0.75803(4) 0.64326(5) 1.20455(3) 0.07393(18) Uani 1 1 d . . .
H4A H 0.341(3) 0.704(3) 0.685(3) 0.052(11) Uiso 1 1 d 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 O1 1.321(4) . ?
C1 C2 1.398(5) . ?
C1 C6 1.425(5) . ?
C2 C3 1.373(5) . ?
C2 H2 0.9300 . ?
C3 C4 1.378(6) . ?
C3 H3 0.9300 . ?
C4 C5 1.355(6) . ?
C4 H4 0.9300 . ?
C5 C6 1.405(5) . ?
C5 H5 0.9300 . ?
C6 C7 1.419(5) . ?
C7 N1 1.277(4) . ?
C7 H7 0.9300 . ?
C8 N1 1.466(7) . ?
C8 C9 1.506(6) . ?
C8 H8A 0.9700 . ?
C8 H8B 0.9700 . ?
C9 N2 1.480(6) . ?
C9 H9A 0.9700 . ?
C9 H9B 0.9700 . ?
C8' C9' 1.509(11) . ?
C8' N1 1.62(4) . ?
C8' H8'1 0.9700 . ?
C8' H8'2 0.9700 . ?
C9' N2 1.50(3) . ?
C9' H9'1 0.9700 . ?
C9' H9'2 0.9700 . ?
C10 N2 1.276(4) . ?
C10 C11 1.442(5) . ?
C10 H10 0.9300 . ?
C11 C12 1.394(5) . ?
C11 C16 1.409(5) . ?
C12 C13 1.365(5) . ?
C12 H12 0.9300 . ?
C13 C14 1.378(5) . ?
C13 Br1 1.902(4) . ?
C14 C15 1.374(5) . ?
C14 H14 0.9300 . ?
C15 C16 1.419(5) . ?
C15 C17 1.493(5) . ?
C16 O2 1.323(4) . ?
C17 N4 1.499(4) . ?
C17 H17A 0.9700 . ?
C17 H17B 0.9700 . ?
C18 N4 1.481(4) . ?
C18 C19 1.494(5) . ?
C18 H18A 0.9700 . ?
C18 H18B 0.9700 . ?
C19 N3 1.438(5) . ?
C19 H19A 0.9700 . ?
C19 H19B 0.9700 . ?
C20 N3 1.434(5) . ?
C20 C21 1.504(5) . ?
C20 H20A 0.9700 . ?
C20 H20B 0.9700 . ?
C21 N4 1.482(5) . ?
C21 H21A 0.9700 . ?
C21 H21B 0.9700 . ?
C22 N3 1.469(5) . ?
C22 H22A 0.9600 . ?
C22 H22B 0.9600 . ?
C22 H22C 0.9600 . ?
N5 C25 1.121(9) . ?
C24 C25 1.435(9) . ?
C24 H24A 0.9600 . ?
C24 H24B 0.9600 . ?
C24 H24C 0.9600 . ?
N1 Cu1 1.915(3) . ?
N2 Cu1 1.928(3) . ?
N4 H4A 0.849(18) . ?
O1 Cu1 1.897(2) . ?
O2 Cu1 1.903(2) . ?
Cl1 O4 1.313(6) . ?
Cl1 O5' 1.364(14) . ?
Cl1 O3 1.372(12) . ?
Cl1 O4' 1.373(8) . ?
Cl1 O6 1.392(12) . ?
Cl1 O6' 1.432(14) . ?
Cl1 O3' 1.452(11) . ?
Cl1 O5 1.461(7) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
O1 C1 C2 118.9(4) . . ?
O1 C1 C6 123.9(3) . . ?
C2 C1 C6 117.2(3) . . ?
C3 C2 C1 121.5(4) . . ?
C3 C2 H2 119.2 . . ?
C1 C2 H2 119.2 . . ?
C2 C3 C4 121.2(4) . . ?
C2 C3 H3 119.4 . . ?
C4 C3 H3 119.4 . . ?
C5 C4 C3 118.9(4) . . ?
C5 C4 H4 120.6 . . ?
C3 C4 H4 120.6 . . ?
C4 C5 C6 122.2(4) . . ?
C4 C5 H5 118.9 . . ?
C6 C5 H5 118.9 . . ?
C5 C6 C7 118.4(4) . . ?
C5 C6 C1 119.0(4) . . ?
C7 C6 C1 122.6(3) . . ?
N1 C7 C6 125.5(4) . . ?
N1 C7 H7 117.2 . . ?
C6 C7 H7 117.2 . . ?
N1 C8 C9 106.2(5) . . ?
N1 C8 H8A 110.5 . . ?
C9 C8 H8A 110.5 . . ?
N1 C8 H8B 110.5 . . ?
C9 C8 H8B 110.5 . . ?
H8A C8 H8B 108.7 . . ?
N2 C9 C8 106.9(5) . . ?
N2 C9 H9A 110.3 . . ?
C8 C9 H9A 110.3 . . ?
N2 C9 H9B 110.3 . . ?
C8 C9 H9B 110.3 . . ?
H9A C9 H9B 108.6 . . ?
C9' C8' N1 104(3) . . ?
C9' C8' H8'1 111.0 . . ?
N1 C8' H8'1 111.0 . . ?
C9' C8' H8'2 111.0 . . ?
N1 C8' H8'2 111.0 . . ?
H8'1 C8' H8'2 109.0 . . ?
N2 C9' C8' 102(3) . . ?
N2 C9' H9'1 111.3 . . ?
C8' C9' H9'1 111.3 . . ?
N2 C9' H9'2 111.3 . . ?
C8' C9' H9'2 111.3 . . ?
H9'1 C9' H9'2 109.2 . . ?
N2 C10 C11 125.1(3) . . ?
N2 C10 H10 117.4 . . ?
C11 C10 H10 117.4 . . ?
C12 C11 C16 119.8(3) . . ?
C12 C11 C10 117.7(3) . . ?
C16 C11 C10 122.4(3) . . ?
C13 C12 C11 120.2(3) . . ?
C13 C12 H12 119.9 . . ?
C11 C12 H12 119.9 . . ?
C12 C13 C14 121.1(3) . . ?
C12 C13 Br1 120.7(3) . . ?
C14 C13 Br1 118.2(3) . . ?
C15 C14 C13 120.3(4) . . ?
C15 C14 H14 119.9 . . ?
C13 C14 H14 119.9 . . ?
C14 C15 C16 120.1(3) . . ?
C14 C15 C17 120.1(3) . . ?
C16 C15 C17 119.6(3) . . ?
O2 C16 C11 124.7(3) . . ?
O2 C16 C15 117.0(3) . . ?
C11 C16 C15 118.3(3) . . ?
C15 C17 N4 112.8(3) . . ?
C15 C17 H17A 109.0 . . ?
N4 C17 H17A 109.0 . . ?
C15 C17 H17B 109.0 . . ?
N4 C17 H17B 109.0 . . ?
H17A C17 H17B 107.8 . . ?
N4 C18 C19 109.3(3) . . ?
N4 C18 H18A 109.8 . . ?
C19 C18 H18A 109.8 . . ?
N4 C18 H18B 109.8 . . ?
C19 C18 H18B 109.8 . . ?
H18A C18 H18B 108.3 . . ?
N3 C19 C18 111.3(3) . . ?
N3 C19 H19A 109.4 . . ?
C18 C19 H19A 109.4 . . ?
N3 C19 H19B 109.4 . . ?
C18 C19 H19B 109.4 . . ?
H19A C19 H19B 108.0 . . ?
N3 C20 C21 111.9(3) . . ?
N3 C20 H20A 109.2 . . ?
C21 C20 H20A 109.2 . . ?
N3 C20 H20B 109.2 . . ?
C21 C20 H20B 109.2 . . ?
H20A C20 H20B 107.9 . . ?
N4 C21 C20 109.2(3) . . ?
N4 C21 H21A 109.8 . . ?
C20 C21 H21A 109.8 . . ?
N4 C21 H21B 109.8 . . ?
C20 C21 H21B 109.8 . . ?
H21A C21 H21B 108.3 . . ?
N3 C22 H22A 109.5 . . ?
N3 C22 H22B 109.5 . . ?
H22A C22 H22B 109.5 . . ?
N3 C22 H22C 109.5 . . ?
H22A C22 H22C 109.5 . . ?
H22B C22 H22C 109.5 . . ?
C25 C24 H24A 109.5 . . ?
C25 C24 H24B 109.5 . . ?
H24A C24 H24B 109.5 . . ?
C25 C24 H24C 109.5 . . ?
H24A C24 H24C 109.5 . . ?
H24B C24 H24C 109.5 . . ?
C7 N1 C8 122.1(4) . . ?
C7 N1 C8' 119.0(11) . . ?
C8 N1 C8' 23.3(14) . . ?
C7 N1 Cu1 126.3(3) . . ?
C8 N1 Cu1 111.6(3) . . ?
C8' N1 Cu1 110.6(14) . . ?
C10 N2 C9 120.5(3) . . ?
C10 N2 C9' 114.2(10) . . ?
C9 N2 C9' 30.8(15) . . ?
C10 N2 Cu1 127.1(3) . . ?
C9 N2 Cu1 112.3(3) . . ?
C9' N2 Cu1 111.7(13) . . ?
C20 N3 C19 109.4(3) . . ?
C20 N3 C22 110.1(3) . . ?
C19 N3 C22 111.0(4) . . ?
C18 N4 C21 110.0(3) . . ?
C18 N4 C17 114.3(3) . . ?
C21 N4 C17 111.5(3) . . ?
C18 N4 H4A 105(2) . . ?
C21 N4 H4A 110(2) . . ?
C17 N4 H4A 106(2) . . ?
N5 C25 C24 178.9(8) . . ?
C1 O1 Cu1 125.8(2) . . ?
C16 O2 Cu1 127.2(2) . . ?
O4 Cl1 O5' 123.9(8) . . ?
O4 Cl1 O3 113.6(7) . . ?
O5' Cl1 O3 115.9(8) . . ?
O4 Cl1 O4' 48.4(6) . . ?
O5' Cl1 O4' 112.7(7) . . ?
O3 Cl1 O4' 126.2(7) . . ?
O4 Cl1 O6 109.3(7) . . ?
O5' Cl1 O6 24.2(9) . . ?
O3 Cl1 O6 114.0(8) . . ?
O4' Cl1 O6 119.8(7) . . ?
O4 Cl1 O6' 128.3(7) . . ?
O5' Cl1 O6' 107.6(8) . . ?
O3 Cl1 O6' 26.4(8) . . ?
O4' Cl1 O6' 115.9(8) . . ?
O6 Cl1 O6' 117.5(8) . . ?
O4 Cl1 O3' 53.4(6) . . ?
O5' Cl1 O3' 119.6(9) . . ?
O3 Cl1 O3' 74.4(8) . . ?
O4' Cl1 O3' 100.6(9) . . ?
O6 Cl1 O3' 95.4(8) . . ?
O6' Cl1 O3' 100.2(8) . . ?
O4 Cl1 O5 103.7(6) . . ?
O5' Cl1 O5 88.9(7) . . ?
O3 Cl1 O5 103.4(6) . . ?
O4' Cl1 O5 55.6(7) . . ?
O6 Cl1 O5 112.2(6) . . ?
O6' Cl1 O5 78.2(7) . . ?
O3' Cl1 O5 149.8(7) . . ?
O1 Cu1 O2 89.16(10) . . ?
O1 Cu1 N1 93.19(12) . . ?
O2 Cu1 N1 175.79(11) . . ?
O1 Cu1 N2 175.25(12) . . ?
O2 Cu1 N2 92.90(11) . . ?
N1 Cu1 N2 84.50(13) . . ?

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
O1 C1 C2 C3 179.4(3) . . . . ?
C6 C1 C2 C3 1.1(5) . . . . ?
C1 C2 C3 C4 -0.1(6) . . . . ?
C2 C3 C4 C5 -1.1(7) . . . . ?
C3 C4 C5 C6 1.3(7) . . . . ?
C4 C5 C6 C7 -179.1(4) . . . . ?
C4 C5 C6 C1 -0.2(6) . . . . ?
O1 C1 C6 C5 -179.1(3) . . . . ?
C2 C1 C6 C5 -1.0(5) . . . . ?
O1 C1 C6 C7 -0.3(5) . . . . ?
C2 C1 C6 C7 177.9(3) . . . . ?
C5 C6 C7 N1 -175.8(4) . . . . ?
C1 C6 C7 N1 5.4(6) . . . . ?
N1 C8 C9 N2 -45.1(11) . . . . ?
N1 C8' C9' N2 52(4) . . . . ?
N2 C10 C11 C12 177.1(3) . . . . ?
N2 C10 C11 C16 -0.1(6) . . . . ?
C16 C11 C12 C13 1.8(5) . . . . ?
C10 C11 C12 C13 -175.5(3) . . . . ?
C11 C12 C13 C14 1.4(5) . . . . ?
C11 C12 C13 Br1 179.7(2) . . . . ?
C12 C13 C14 C15 -2.5(6) . . . . ?
Br1 C13 C14 C15 179.1(3) . . . . ?
C13 C14 C15 C16 0.4(5) . . . . ?
C13 C14 C15 C17 -175.5(3) . . . . ?
C12 C11 C16 O2 178.4(3) . . . . ?
C10 C11 C16 O2 -4.4(5) . . . . ?
C12 C11 C16 C15 -3.7(5) . . . . ?
C10 C11 C16 C15 173.4(3) . . . . ?
C14 C15 C16 O2 -179.4(3) . . . . ?
C17 C15 C16 O2 -3.4(5) . . . . ?
C14 C15 C16 C11 2.6(5) . . . . ?
C17 C15 C16 C11 178.6(3) . . . . ?
C14 C15 C17 N4 -139.2(3) . . . . ?
C16 C15 C17 N4 44.9(4) . . . . ?
N4 C18 C19 N3 -59.5(4) . . . . ?
N3 C20 C21 N4 57.5(5) . . . . ?
C6 C7 N1 C8 -173.4(5) . . . . ?
C6 C7 N1 C8' 159.7(19) . . . . ?
C6 C7 N1 Cu1 4.7(5) . . . . ?
C9 C8 N1 C7 -140.8(6) . . . . ?
C9 C8 N1 C8' -51(3) . . . . ?
C9 C8 N1 Cu1 40.9(9) . . . . ?
C9' C8' N1 C7 167(3) . . . . ?
C9' C8' N1 C8 62(2) . . . . ?
C9' C8' N1 Cu1 -35(4) . . . . ?
C11 C10 N2 C9 -170.2(5) . . . . ?
C11 C10 N2 C9' 156(2) . . . . ?
C11 C10 N2 Cu1 7.7(5) . . . . ?
C8 C9 N2 C10 -150.7(6) . . . . ?
C8 C9 N2 C9' -64(2) . . . . ?
C8 C9 N2 Cu1 31.1(9) . . . . ?
C8' C9' N2 C10 156(3) . . . . ?
C8' C9' N2 C9 46(3) . . . . ?
C8' C9' N2 Cu1 -51(4) . . . . ?
C21 C20 N3 C19 -59.1(4) . . . . ?
C21 C20 N3 C22 178.7(4) . . . . ?
C18 C19 N3 C20 60.0(4) . . . . ?
C18 C19 N3 C22 -178.3(3) . . . . ?
C19 C18 N4 C21 57.2(4) . . . . ?
C19 C18 N4 C17 -176.5(3) . . . . ?
C20 C21 N4 C18 -56.0(4) . . . . ?
C20 C21 N4 C17 176.2(3) . . . . ?
C15 C17 N4 C18 59.8(4) . . . . ?
C15 C17 N4 C21 -174.7(3) . . . . ?
C2 C1 O1 Cu1 167.6(2) . . . . ?
C6 C1 O1 Cu1 -14.2(5) . . . . ?
C11 C16 O2 Cu1 0.8(4) . . . . ?
C15 C16 O2 Cu1 -177.1(2) . . . . ?
C1 O1 Cu1 O2 -158.4(3) . . . . ?
C1 O1 Cu1 N1 18.1(3) . . . . ?
C1 O1 Cu1 N2 -42.6(15) . . . . ?
C16 O2 Cu1 O1 -179.8(3) . . . . ?
C16 O2 Cu1 N1 56.1(16) . . . . ?
C16 O2 Cu1 N2 4.4(3) . . . . ?
C7 N1 Cu1 O1 -13.6(3) . . . . ?
C8 N1 Cu1 O1 164.7(4) . . . . ?
C8' N1 Cu1 O1 -170.3(15) . . . . ?
C7 N1 Cu1 O2 110.4(15) . . . . ?
C8 N1 Cu1 O2 -71.4(17) . . . . ?
C8' N1 Cu1 O2 -46(2) . . . . ?
C7 N1 Cu1 N2 162.3(3) . . . . ?
C8 N1 Cu1 N2 -19.5(4) . . . . ?
C8' N1 Cu1 N2 5.5(15) . . . . ?
C10 N2 Cu1 O1 -124.2(13) . . . . ?
C9 N2 Cu1 O1 53.8(15) . . . . ?
C9' N2 Cu1 O1 87(2) . . . . ?
C10 N2 Cu1 O2 -8.6(3) . . . . ?
C9 N2 Cu1 O2 169.4(4) . . . . ?
C9' N2 Cu1 O2 -157.3(18) . . . . ?
C10 N2 Cu1 N1 174.7(3) . . . . ?
C9 N2 Cu1 N1 -7.3(4) . . . . ?
C9' N2 Cu1 N1 26.0(18) . . . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
N4 H4A O2 0.849(18) 1.95(3) 2.620(4) 135(3) .

_diffrn_measured_fraction_theta_max 0.989
_diffrn_reflns_theta_full        25.00
_diffrn_measured_fraction_theta_full 0.989
_refine_diff_density_max         0.566
_refine_diff_density_min         -0.320
_refine_diff_density_rms         0.060
_database_code_depnum_ccdc_archive 'CCDC 978676'
