# Electronic Supplementary Material (ESI) for RSC Advances.
# This journal is © The Royal Society of Chemistry 2015

####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_new
_database_code_depnum_ccdc_archive 'CCDC 999645'
_audit_update_record             
;
2014-07-29 deposited with the CCDC.
2015-06-03 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
 ?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C25 H33 Cl Cu2 N6 O10'
_chemical_formula_weight         740.10

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'

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

_cell_length_a                   7.9614(8)
_cell_length_b                   23.877(2)
_cell_length_c                   8.4244(8)
_cell_angle_alpha                90.00
_cell_angle_beta                 109.146(3)
_cell_angle_gamma                90.00
_cell_volume                     1512.8(3)
_cell_formula_units_Z            2
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    ?
_cell_measurement_theta_min      ?
_cell_measurement_theta_max      ?

_exptl_crystal_description       prism
_exptl_crystal_colour            'dark green'
_exptl_crystal_size_max          0.54
_exptl_crystal_size_mid          0.38
_exptl_crystal_size_min          0.15
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.625
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             760
_exptl_absorpt_coefficient_mu    1.558
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.4866
_exptl_absorpt_correction_T_max  0.7999
_exptl_absorpt_process_details   ?

_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      296(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  ?
_diffrn_measurement_method       ?
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            23225
_diffrn_reflns_av_R_equivalents  0.0339
_diffrn_reflns_av_sigmaI/netI    0.0445
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       -31
_diffrn_reflns_limit_k_max       29
_diffrn_reflns_limit_l_min       -10
_diffrn_reflns_limit_l_max       10
_diffrn_reflns_theta_min         3.06
_diffrn_reflns_theta_max         27.54
_reflns_number_total             6842
_reflns_number_gt                6074
_reflns_threshold_expression     >2σ(I)

_computing_data_collection       'Bruker SMART'
_computing_cell_refinement       'Bruker SMART'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_molecular_graphics    XP
_computing_publication_material  WinGX

_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 > 2σ(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)+(0.1140P)²+3.8838P] 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_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0.08(2)
_refine_ls_number_reflns         6842
_refine_ls_number_parameters     406
_refine_ls_number_restraints     15
_refine_ls_R_factor_all          0.0744
_refine_ls_R_factor_gt           0.0669
_refine_ls_wR_factor_ref         0.1964
_refine_ls_wR_factor_gt          0.1913
_refine_ls_goodness_of_fit_ref   1.062
_refine_ls_restrained_S_all      1.062
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
Cu1 Cu 0.32097(11) 0.43678(3) 0.15514(10) 0.0351(2) Uani 1 1 d . . .
Cu2 Cu 0.76125(11) 0.34659(3) 0.69224(9) 0.0357(2) Uani 1 1 d . . .
Cl1 Cl 0.6456(3) 0.19421(9) -0.0492(3) 0.0581(5) Uani 1 1 d . . .
O1 O 0.2533(7) 0.4039(2) -0.0692(6) 0.0418(12) Uani 1 1 d . . .
O2 O 0.6511(7) 0.3264(2) 0.4559(6) 0.0376(11) Uani 1 1 d . . .
O3 O 0.5908(7) 0.4091(2) 0.6389(6) 0.0409(12) Uani 1 1 d . . .
O4 O 0.5481(10) 0.4964(3) 0.0917(10) 0.0639(17) Uani 1 1 d . . .
H4 H 0.6286 0.5070 0.1793 0.096 Uiso 1 1 d R . .
O5 O 0.9698(7) 0.4058(2) 0.6501(7) 0.0435(12) Uani 1 1 d . . .
H5A H 1.0697 0.4100 0.7303 0.065 Uiso 1 1 d R . .
H5B H 0.9457 0.4359 0.5939 0.065 Uiso 1 1 d R . .
N1 N 0.4532(7) 0.3681(2) 0.2194(6) 0.0310(11) Uani 1 1 d . . .
N2 N 0.3886(8) 0.4474(3) 0.4021(7) 0.0379(14) Uani 1 1 d . . .
N3 N 0.1973(11) 0.5090(3) 0.0876(9) 0.0531(18) Uani 1 1 d . . .
H3A H 0.0787 0.5020 0.0430 0.064 Uiso 1 1 calc R . .
N4 N 0.9093(7) 0.2779(3) 0.7434(7) 0.0335(12) Uani 1 1 d . . .
N5 N 0.8447(7) 0.3532(3) 0.9405(6) 0.0335(12) Uani 1 1 d . . .
C1 C 0.3443(9) 0.3568(3) -0.0689(8) 0.0359(14) Uani 1 1 d . . .
C2 C 0.4547(9) 0.3345(3) 0.0853(8) 0.0319(13) Uani 1 1 d . . .
C3 C 0.5444(9) 0.2839(3) 0.0927(8) 0.0351(13) Uani 1 1 d . . .
H3 H 0.6111 0.2685 0.1954 0.042 Uiso 1 1 calc R . .
C4 C 0.5320(9) 0.2573(3) -0.0550(10) 0.0381(14) Uani 1 1 d . . .
C5 C 0.4321(11) 0.2779(4) -0.2050(9) 0.0467(18) Uani 1 1 d . . .
H5 H 0.4248 0.2586 -0.3030 0.056 Uiso 1 1 calc R . .
C6 C 0.3396(10) 0.3282(4) -0.2141(9) 0.0443(17) Uani 1 1 d . . .
H6 H 0.2739 0.3426 -0.3185 0.053 Uiso 1 1 calc R . .
C7 C 0.5425(8) 0.3633(3) 0.3800(7) 0.0294(12) Uani 1 1 d . . .
C8 C 0.5012(10) 0.4111(3) 0.4826(9) 0.0352(14) Uani 1 1 d . . .
C9 C 0.3409(14) 0.4922(4) 0.4930(12) 0.061(2) Uani 1 1 d D . .
H9A H 0.4449 0.5150 0.5462 0.073 Uiso 1 1 calc R . .
H9B H 0.3009 0.4766 0.5807 0.073 Uiso 1 1 calc R . .
C10 C 0.1941(15) 0.5289(5) 0.3782(13) 0.077(3) Uani 1 1 d D . .
H10A H 0.0841 0.5077 0.3457 0.092 Uiso 1 1 calc R . .
H10B H 0.1782 0.5609 0.4426 0.092 Uiso 1 1 calc R . .
C11 C 0.223(2) 0.5505(5) 0.2193(14) 0.096(5) Uani 1 1 d D . .
H11A H 0.1420 0.5814 0.1755 0.115 Uiso 1 1 calc R . .
H11B H 0.3431 0.5650 0.2485 0.115 Uiso 1 1 calc R . .
C12 C 0.2568(15) 0.5345(5) -0.045(2) 0.091(4) Uani 1 1 d D . .
H12A H 0.1992 0.5706 -0.0749 0.109 Uiso 1 1 calc R . .
H12B H 0.2173 0.5109 -0.1443 0.109 Uiso 1 1 calc R . .
C13 C 0.4573(16) 0.5427(6) 0.0028(19) 0.095(5) Uani 1 1 d D . .
H13A H 0.4889 0.5479 -0.0980 0.114 Uiso 1 1 calc R . .
H13B H 0.4922 0.5761 0.0715 0.114 Uiso 1 1 calc R . .
C14 C 0.9309(13) 0.2419(4) 0.6308(11) 0.0498(19) Uani 1 1 d . . .
H14 H 0.8753 0.2493 0.5173 0.060 Uiso 1 1 calc R . .
C15 C 1.0357(12) 0.1927(4) 0.6776(13) 0.055(2) Uani 1 1 d . . .
H15 H 1.0466 0.1673 0.5979 0.066 Uiso 1 1 calc R . .
C16 C 1.1194(13) 0.1846(4) 0.8447(14) 0.060(2) Uani 1 1 d . . .
H16 H 1.1910 0.1533 0.8814 0.072 Uiso 1 1 calc R . .
C17 C 1.0986(12) 0.2228(4) 0.9608(11) 0.0507(19) Uani 1 1 d . . .
H17 H 1.1551 0.2167 1.0750 0.061 Uiso 1 1 calc R . .
C18 C 0.9952(8) 0.2695(3) 0.9080(8) 0.0358(14) Uani 1 1 d . . .
C19 C 0.9579(10) 0.3121(3) 1.0184(8) 0.0349(14) Uani 1 1 d . . .
C20 C 1.0370(11) 0.3101(4) 1.1923(9) 0.0472(18) Uani 1 1 d . . .
H20 H 1.1156 0.2815 1.2436 0.057 Uiso 1 1 calc R . .
C21 C 0.9945(11) 0.3523(5) 1.2866(9) 0.056(2) Uani 1 1 d . . .
H21 H 1.0454 0.3530 1.4029 0.068 Uiso 1 1 calc R . .
C22 C 0.8737(12) 0.3934(4) 1.2025(10) 0.0491(18) Uani 1 1 d . . .
H22 H 0.8410 0.4216 1.2627 0.059 Uiso 1 1 calc R . .
C23 C 0.8029(11) 0.3921(3) 1.0289(9) 0.0431(16) Uani 1 1 d . . .
H23 H 0.7231 0.4199 0.9739 0.052 Uiso 1 1 calc R . .
O6A O 0.824(2) 0.5102(7) 0.841(2) 0.081(4) Uani 0.60 1 d PU A 1
H6A H 0.8260 0.5350 0.7645 0.122 Uiso 0.60 1 d PR A 1
H6B H 0.7486 0.4854 0.7942 0.122 Uiso 0.60 1 d PR A 1
O6B O 0.823(5) 0.5346(13) 0.927(4) 0.110(9) Uani 0.40 1 d PU B 2
H6C H 0.7494 0.5118 0.9408 0.166 Uiso 0.40 1 d PR B 2
H6D H 0.8009 0.5404 0.8116 0.166 Uiso 0.40 1 d PR B 2
N6 N 0.8080(14) 0.5528(4) 0.4664(13) 0.068(2) Uani 1 1 d . . .
O7 O 0.7938(13) 0.5003(4) 0.4484(13) 0.087(2) Uani 1 1 d . . .
O8 O 0.7305(19) 0.5811(5) 0.3501(17) 0.125(4) Uani 1 1 d . . .
O9 O 0.8930(16) 0.5752(8) 0.5983(16) 0.140(5) Uani 1 1 d . . .
O10 O 0.7442(18) 0.6895(5) 0.6228(15) 0.122(4) Uani 1 1 d DU . .
H10 H 0.7911 0.6571 0.6265 0.183 Uiso 1 1 d R . .
C24 C 0.5565(19) 0.6842(6) 0.5641(18) 0.105(4) Uani 1 1 d DU . .
H24A H 0.5185 0.6683 0.4519 0.126 Uiso 1 1 calc R . .
H24B H 0.5032 0.7210 0.5577 0.126 Uiso 1 1 calc R . .
C25 C 0.492(3) 0.6470(6) 0.679(2) 0.106(5) Uani 1 1 d DU . .
H25A H 0.3644 0.6440 0.6355 0.159 Uiso 1 1 calc R . .
H25B H 0.5263 0.6631 0.7897 0.159 Uiso 1 1 calc R . .
H25C H 0.5433 0.6104 0.6851 0.159 Uiso 1 1 calc R . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Cu1 N1 1.928(5) . ?
Cu1 O1 1.952(5) . ?
Cu1 N3 1.975(7) . ?
Cu1 N2 1.987(6) . ?
Cu1 O4 2.492(7) . ?
Cu2 O2 1.954(5) . ?
Cu2 O3 1.967(5) . ?
Cu2 N5 1.982(5) . ?
Cu2 N4 1.984(6) . ?
Cu2 O5 2.295(6) . ?
Cl1 C4 1.750(7) . ?
O1 C1 1.339(9) . ?
O2 C7 1.253(8) . ?
O3 C8 1.276(9) . ?
O4 C13 1.397(13) . ?
O4 H4 0.8425 . ?
O5 H5A 0.8642 . ?
O5 H5B 0.8484 . ?
N1 C7 1.311(8) . ?
N1 C2 1.389(8) . ?
N2 C8 1.270(9) . ?
N2 C9 1.438(10) . ?
N3 C11 1.450(14) . ?
N3 C12 1.480(16) . ?
N3 H3A 0.9100 . ?
N4 C14 1.331(10) . ?
N4 C18 1.345(8) . ?
N5 C23 1.301(10) . ?
N5 C19 1.347(9) . ?
C1 C6 1.391(10) . ?
C1 C2 1.412(9) . ?
C2 C3 1.395(10) . ?
C3 C4 1.370(10) . ?
C3 H3 0.9300 . ?
C4 C5 1.346(12) . ?
C5 C6 1.398(13) . ?
C5 H5 0.9300 . ?
C6 H6 0.9300 . ?
C7 C8 1.531(8) . ?
C9 C10 1.526(8) . ?
C9 H9A 0.9700 . ?
C9 H9B 0.9700 . ?
C10 C11 1.520(9) . ?
C10 H10A 0.9700 . ?
C10 H10B 0.9700 . ?
C11 H11A 0.9700 . ?
C11 H11B 0.9700 . ?
C12 C13 1.526(9) . ?
C12 H12A 0.9700 . ?
C12 H12B 0.9700 . ?
C13 H13A 0.9700 . ?
C13 H13B 0.9700 . ?
C14 C15 1.420(13) . ?
C14 H14 0.9300 . ?
C15 C16 1.359(15) . ?
C15 H15 0.9300 . ?
C16 C17 1.386(14) . ?
C16 H16 0.9300 . ?
C17 C18 1.370(11) . ?
C17 H17 0.9300 . ?
C18 C19 1.474(10) . ?
C19 C20 1.393(10) . ?
C20 C21 1.391(13) . ?
C20 H20 0.9300 . ?
C21 C22 1.394(14) . ?
C21 H21 0.9300 . ?
C22 C23 1.384(11) . ?
C22 H22 0.9300 . ?
C23 H23 0.9300 . ?
O6A H6A 0.8792 . ?
O6A H6B 0.8420 . ?
O6A H6C 1.1767 . ?
O6A H6D 0.7629 . ?
O6B H6A 1.3802 . ?
O6B H6C 0.8354 . ?
O6B H6D 0.9431 . ?
N6 O8 1.184(14) . ?
N6 O9 1.218(14) . ?
N6 O7 1.264(12) . ?
O10 C24 1.418(9) . ?
O10 H10 0.8538 . ?
C24 C25 1.525(9) . ?
C24 H24A 0.9700 . ?
C24 H24B 0.9700 . ?
C25 H25A 0.9600 . ?
C25 H25B 0.9600 . ?
C25 H25C 0.9600 . ?

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 Cu1 O1 83.2(2) . . ?
N1 Cu1 N3 176.8(3) . . ?
O1 Cu1 N3 96.8(3) . . ?
N1 Cu1 N2 83.0(2) . . ?
O1 Cu1 N2 163.6(2) . . ?
N3 Cu1 N2 97.4(3) . . ?
N1 Cu1 O4 100.2(2) . . ?
O1 Cu1 O4 90.6(3) . . ?
N3 Cu1 O4 76.6(3) . . ?
N2 Cu1 O4 100.7(3) . . ?
O2 Cu2 O3 84.8(2) . . ?
O2 Cu2 N5 167.8(2) . . ?
O3 Cu2 N5 98.5(2) . . ?
O2 Cu2 N4 93.1(2) . . ?
O3 Cu2 N4 173.4(2) . . ?
N5 Cu2 N4 82.3(2) . . ?
O2 Cu2 O5 95.7(2) . . ?
O3 Cu2 O5 88.7(2) . . ?
N5 Cu2 O5 96.0(2) . . ?
N4 Cu2 O5 97.7(2) . . ?
C1 O1 Cu1 111.0(4) . . ?
C7 O2 Cu2 110.5(4) . . ?
C8 O3 Cu2 112.0(4) . . ?
C13 O4 Cu1 106.4(6) . . ?
C13 O4 H4 110.0 . . ?
Cu1 O4 H4 112.4 . . ?
Cu2 O5 H5A 118.6 . . ?
Cu2 O5 H5B 124.5 . . ?
H5A O5 H5B 108.5 . . ?
C7 N1 C2 130.0(6) . . ?
C7 N1 Cu1 115.2(5) . . ?
C2 N1 Cu1 114.4(4) . . ?
C8 N2 C9 119.1(6) . . ?
C8 N2 Cu1 112.0(5) . . ?
C9 N2 Cu1 128.6(5) . . ?
C11 N3 C12 107.4(10) . . ?
C11 N3 Cu1 116.3(6) . . ?
C12 N3 Cu1 108.9(6) . . ?
C11 N3 H3A 108.0 . . ?
C12 N3 H3A 108.0 . . ?
Cu1 N3 H3A 108.0 . . ?
C14 N4 C18 119.8(7) . . ?
C14 N4 Cu2 125.8(5) . . ?
C18 N4 Cu2 114.4(5) . . ?
C23 N5 C19 119.8(6) . . ?
C23 N5 Cu2 126.9(5) . . ?
C19 N5 Cu2 113.3(5) . . ?
O1 C1 C6 123.6(6) . . ?
O1 C1 C2 119.5(6) . . ?
C6 C1 C2 116.9(7) . . ?
N1 C2 C3 127.2(6) . . ?
N1 C2 C1 111.2(6) . . ?
C3 C2 C1 121.5(6) . . ?
C4 C3 C2 118.5(7) . . ?
C4 C3 H3 120.8 . . ?
C2 C3 H3 120.8 . . ?
C5 C4 C3 121.9(7) . . ?
C5 C4 Cl1 118.7(6) . . ?
C3 C4 Cl1 119.3(6) . . ?
C4 C5 C6 120.2(7) . . ?
C4 C5 H5 119.9 . . ?
C6 C5 H5 119.9 . . ?
C1 C6 C5 120.8(7) . . ?
C1 C6 H6 119.6 . . ?
C5 C6 H6 119.6 . . ?
O2 C7 N1 129.6(6) . . ?
O2 C7 C8 118.4(5) . . ?
N1 C7 C8 111.9(6) . . ?
N2 C8 O3 129.4(6) . . ?
N2 C8 C7 116.8(6) . . ?
O3 C8 C7 113.7(6) . . ?
N2 C9 C10 111.8(8) . . ?
N2 C9 H9A 109.3 . . ?
C10 C9 H9A 109.3 . . ?
N2 C9 H9B 109.3 . . ?
C10 C9 H9B 109.3 . . ?
H9A C9 H9B 107.9 . . ?
C11 C10 C9 116.6(9) . . ?
C11 C10 H10A 108.1 . . ?
C9 C10 H10A 108.1 . . ?
C11 C10 H10B 108.1 . . ?
C9 C10 H10B 108.1 . . ?
H10A C10 H10B 107.3 . . ?
N3 C11 C10 114.7(11) . . ?
N3 C11 H11A 108.6 . . ?
C10 C11 H11A 108.6 . . ?
N3 C11 H11B 108.6 . . ?
C10 C11 H11B 108.6 . . ?
H11A C11 H11B 107.6 . . ?
N3 C12 C13 114.8(10) . . ?
N3 C12 H12A 108.6 . . ?
C13 C12 H12A 108.6 . . ?
N3 C12 H12B 108.6 . . ?
C13 C12 H12B 108.6 . . ?
H12A C12 H12B 107.6 . . ?
O4 C13 C12 110.6(9) . . ?
O4 C13 H13A 109.5 . . ?
C12 C13 H13A 109.5 . . ?
O4 C13 H13B 109.5 . . ?
C12 C13 H13B 109.5 . . ?
H13A C13 H13B 108.1 . . ?
N4 C14 C15 122.5(8) . . ?
N4 C14 H14 118.8 . . ?
C15 C14 H14 118.8 . . ?
C16 C15 C14 116.7(8) . . ?
C16 C15 H15 121.6 . . ?
C14 C15 H15 121.6 . . ?
C15 C16 C17 120.4(8) . . ?
C15 C16 H16 119.8 . . ?
C17 C16 H16 119.8 . . ?
C18 C17 C16 120.3(8) . . ?
C18 C17 H17 119.9 . . ?
C16 C17 H17 119.9 . . ?
N4 C18 C17 120.3(7) . . ?
N4 C18 C19 114.1(6) . . ?
C17 C18 C19 125.5(7) . . ?
N5 C19 C20 122.5(7) . . ?
N5 C19 C18 115.9(6) . . ?
C20 C19 C18 121.6(7) . . ?
C21 C20 C19 117.6(8) . . ?
C21 C20 H20 121.2 . . ?
C19 C20 H20 121.2 . . ?
C20 C21 C22 118.4(7) . . ?
C20 C21 H21 120.8 . . ?
C22 C21 H21 120.8 . . ?
C23 C22 C21 119.7(8) . . ?
C23 C22 H22 120.2 . . ?
C21 C22 H22 120.2 . . ?
N5 C23 C22 121.9(8) . . ?
N5 C23 H23 119.1 . . ?
C22 C23 H23 119.1 . . ?
H6A O6A H6B 108.1 . . ?
H6A O6A H6C 129.8 . . ?
H6B O6A H6C 84.9 . . ?
H6A O6A H6D 35.7 . . ?
H6B O6A H6D 117.0 . . ?
H6C O6A H6D 94.7 . . ?
H6A O6B H6C 112.4 . . ?
H6A O6B H6D 13.7 . . ?
H6C O6B H6D 109.5 . . ?
O8 N6 O9 119.2(13) . . ?
O8 N6 O7 117.7(11) . . ?
O9 N6 O7 123.0(14) . . ?
C24 O10 H10 109.3 . . ?
O10 C24 C25 111.6(12) . . ?
O10 C24 H24A 109.3 . . ?
C25 C24 H24A 109.3 . . ?
O10 C24 H24B 109.3 . . ?
C25 C24 H24B 109.3 . . ?
H24A C24 H24B 108.0 . . ?
C24 C25 H25A 109.5 . . ?
C24 C25 H25B 109.5 . . ?
H25A C25 H25B 109.5 . . ?
C24 C25 H25C 109.5 . . ?
H25A C25 H25C 109.5 . . ?
H25B C25 H25C 109.5 . . ?

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 Cu1 O1 C1 -7.4(5) . . . . ?
N3 Cu1 O1 C1 169.4(5) . . . . ?
N2 Cu1 O1 C1 -40.9(11) . . . . ?
O4 Cu1 O1 C1 92.8(5) . . . . ?
O3 Cu2 O2 C7 6.4(5) . . . . ?
N5 Cu2 O2 C7 112.9(11) . . . . ?
N4 Cu2 O2 C7 -179.9(5) . . . . ?
O5 Cu2 O2 C7 -81.8(5) . . . . ?
O2 Cu2 O3 C8 -5.1(5) . . . . ?
N5 Cu2 O3 C8 -173.3(5) . . . . ?
N4 Cu2 O3 C8 -76(2) . . . . ?
O5 Cu2 O3 C8 90.8(5) . . . . ?
N1 Cu1 O4 C13 165.2(8) . . . . ?
O1 Cu1 O4 C13 82.0(8) . . . . ?
N3 Cu1 O4 C13 -14.9(8) . . . . ?
N2 Cu1 O4 C13 -110.0(8) . . . . ?
O1 Cu1 N1 C7 -180.0(5) . . . . ?
N3 Cu1 N1 C7 89(5) . . . . ?
N2 Cu1 N1 C7 -9.0(5) . . . . ?
O4 Cu1 N1 C7 90.6(5) . . . . ?
O1 Cu1 N1 C2 7.0(5) . . . . ?
N3 Cu1 N1 C2 -84(5) . . . . ?
N2 Cu1 N1 C2 178.0(5) . . . . ?
O4 Cu1 N1 C2 -82.4(5) . . . . ?
N1 Cu1 N2 C8 9.2(5) . . . . ?
O1 Cu1 N2 C8 42.7(12) . . . . ?
N3 Cu1 N2 C8 -167.6(6) . . . . ?
O4 Cu1 N2 C8 -90.0(6) . . . . ?
N1 Cu1 N2 C9 -177.5(8) . . . . ?
O1 Cu1 N2 C9 -144.0(9) . . . . ?
N3 Cu1 N2 C9 5.7(8) . . . . ?
O4 Cu1 N2 C9 83.3(8) . . . . ?
N1 Cu1 N3 C11 -85(5) . . . . ?
O1 Cu1 N3 C11 -175.5(9) . . . . ?
N2 Cu1 N3 C11 12.7(10) . . . . ?
O4 Cu1 N3 C11 -86.5(9) . . . . ?
N1 Cu1 N3 C12 36(5) . . . . ?
O1 Cu1 N3 C12 -54.2(8) . . . . ?
N2 Cu1 N3 C12 134.1(7) . . . . ?
O4 Cu1 N3 C12 34.9(7) . . . . ?
O2 Cu2 N4 C14 10.6(7) . . . . ?
O3 Cu2 N4 C14 81(2) . . . . ?
N5 Cu2 N4 C14 179.3(7) . . . . ?
O5 Cu2 N4 C14 -85.6(7) . . . . ?
O2 Cu2 N4 C18 -170.8(5) . . . . ?
O3 Cu2 N4 C18 -100(2) . . . . ?
N5 Cu2 N4 C18 -2.1(5) . . . . ?
O5 Cu2 N4 C18 93.0(5) . . . . ?
O2 Cu2 N5 C23 -110.5(12) . . . . ?
O3 Cu2 N5 C23 -5.4(6) . . . . ?
N4 Cu2 N5 C23 -178.8(6) . . . . ?
O5 Cu2 N5 C23 84.2(6) . . . . ?
O2 Cu2 N5 C19 70.3(13) . . . . ?
O3 Cu2 N5 C19 175.4(5) . . . . ?
N4 Cu2 N5 C19 2.0(5) . . . . ?
O5 Cu2 N5 C19 -95.0(5) . . . . ?
Cu1 O1 C1 C6 -171.9(6) . . . . ?
Cu1 O1 C1 C2 6.9(8) . . . . ?
C7 N1 C2 C3 5.6(12) . . . . ?
Cu1 N1 C2 C3 177.3(6) . . . . ?
C7 N1 C2 C1 -176.8(7) . . . . ?
Cu1 N1 C2 C1 -5.1(7) . . . . ?
O1 C1 C2 N1 -1.3(9) . . . . ?
C6 C1 C2 N1 177.6(6) . . . . ?
O1 C1 C2 C3 176.4(6) . . . . ?
C6 C1 C2 C3 -4.7(10) . . . . ?
N1 C2 C3 C4 -178.8(7) . . . . ?
C1 C2 C3 C4 3.9(10) . . . . ?
C2 C3 C4 C5 -2.0(11) . . . . ?
C2 C3 C4 Cl1 179.2(5) . . . . ?
C3 C4 C5 C6 1.1(12) . . . . ?
Cl1 C4 C5 C6 179.9(6) . . . . ?
O1 C1 C6 C5 -177.4(7) . . . . ?
C2 C1 C6 C5 3.7(11) . . . . ?
C4 C5 C6 C1 -2.0(12) . . . . ?
Cu2 O2 C7 N1 173.5(6) . . . . ?
Cu2 O2 C7 C8 -6.7(7) . . . . ?
C2 N1 C7 O2 -1.4(12) . . . . ?
Cu1 N1 C7 O2 -173.1(6) . . . . ?
C2 N1 C7 C8 178.8(6) . . . . ?
Cu1 N1 C7 C8 7.1(7) . . . . ?
C9 N2 C8 O3 -4.0(13) . . . . ?
Cu1 N2 C8 O3 170.1(7) . . . . ?
C9 N2 C8 C7 178.1(7) . . . . ?
Cu1 N2 C8 C7 -7.9(8) . . . . ?
Cu2 O3 C8 N2 -175.1(7) . . . . ?
Cu2 O3 C8 C7 2.9(7) . . . . ?
O2 C7 C8 N2 -179.0(7) . . . . ?
N1 C7 C8 N2 0.8(9) . . . . ?
O2 C7 C8 O3 2.7(9) . . . . ?
N1 C7 C8 O3 -177.5(6) . . . . ?
C8 N2 C9 C10 -175.6(9) . . . . ?
Cu1 N2 C9 C10 11.5(13) . . . . ?
N2 C9 C10 C11 -50.7(15) . . . . ?
C12 N3 C11 C10 -171.6(10) . . . . ?
Cu1 N3 C11 C10 -49.4(14) . . . . ?
C9 C10 C11 N3 75.2(16) . . . . ?
C11 N3 C12 C13 70.5(14) . . . . ?
Cu1 N3 C12 C13 -56.2(13) . . . . ?
Cu1 O4 C13 C12 -9.2(14) . . . . ?
N3 C12 C13 O4 41.1(17) . . . . ?
C18 N4 C14 C15 3.2(13) . . . . ?
Cu2 N4 C14 C15 -178.3(7) . . . . ?
N4 C14 C15 C16 -2.2(14) . . . . ?
C14 C15 C16 C17 1.0(14) . . . . ?
C15 C16 C17 C18 -0.8(14) . . . . ?
C14 N4 C18 C17 -2.9(11) . . . . ?
Cu2 N4 C18 C17 178.4(6) . . . . ?
C14 N4 C18 C19 -179.5(7) . . . . ?
Cu2 N4 C18 C19 1.8(7) . . . . ?
C16 C17 C18 N4 1.7(12) . . . . ?
C16 C17 C18 C19 177.9(8) . . . . ?
C23 N5 C19 C20 -1.6(10) . . . . ?
Cu2 N5 C19 C20 177.6(6) . . . . ?
C23 N5 C19 C18 179.1(6) . . . . ?
Cu2 N5 C19 C18 -1.6(7) . . . . ?
N4 C18 C19 N5 -0.1(8) . . . . ?
C17 C18 C19 N5 -176.5(7) . . . . ?
N4 C18 C19 C20 -179.4(7) . . . . ?
C17 C18 C19 C20 4.2(11) . . . . ?
N5 C19 C20 C21 0.5(12) . . . . ?
C18 C19 C20 C21 179.8(7) . . . . ?
C19 C20 C21 C22 1.0(13) . . . . ?
C20 C21 C22 C23 -1.5(13) . . . . ?
C19 N5 C23 C22 1.1(11) . . . . ?
Cu2 N5 C23 C22 -178.0(6) . . . . ?
C21 C22 C23 N5 0.5(12) . . . . ?

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
N3 H3A O6A 0.91 2.19 3.018(18) 151.3 1_454
N3 H3A O6B 0.91 2.10 2.90(3) 147.2 1_454
O4 H4 O7 0.84 2.22 3.001(13) 153.8 .
O4 H4 O8 0.84 2.26 2.978(16) 143.7 .
O5 H5A O1 0.86 1.84 2.681(7) 163.3 1_656
O5 H5B O7 0.85 2.09 2.895(10) 159.1 .
O6A H6B O3 0.84 2.35 3.18(2) 166.7 .
O6A H6A O9 0.88 1.91 2.76(2) 162.2 .
O6B H6C O4 0.84 2.38 3.09(4) 143.1 1_556
O6B H6D O9 0.94 2.31 3.15(4) 149.2 .
O10 H10 O9 0.85 2.16 3.01(2) 172.0 .
C17 H17 O10 0.93 2.49 3.410(14) 169.1 2_747
C20 H20 O10 0.93 2.55 3.461(13) 165.0 2_747
C22 H22 O7 0.93 2.55 3.475(13) 172.6 1_556

_diffrn_measured_fraction_theta_max 0.994
_diffrn_reflns_theta_full        27.54
_diffrn_measured_fraction_theta_full 0.994
_refine_diff_density_max         0.937
_refine_diff_density_min         -1.325
_refine_diff_density_rms         0.133
_exptl_crystal_recrystallization_method 'Re-crystallisation from solvent: '
####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_a26
_database_code_depnum_ccdc_archive 'CCDC 999745'
_audit_update_record             
;
2014-07-29 deposited with the CCDC.
2015-06-03 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
 ?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C22 H29 Cl2 Cu2 N5 O7'
_chemical_formula_weight         673.48

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           triclinic
_symmetry_space_group_name_H-M   'P -1'

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

_cell_length_a                   10.9647(8)
_cell_length_b                   11.4494(9)
_cell_length_c                   11.6578(9)
_cell_angle_alpha                85.9120(10)
_cell_angle_beta                 74.6800(10)
_cell_angle_gamma                71.0260(10)
_cell_volume                     1334.64(18)
_cell_formula_units_Z            2
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    ?
_cell_measurement_theta_min      ?
_cell_measurement_theta_max      ?

_exptl_crystal_description       prism
_exptl_crystal_colour            'dark brown'
_exptl_crystal_size_max          0.37
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.07
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.676
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             688
_exptl_absorpt_coefficient_mu    1.845
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.5484
_exptl_absorpt_correction_T_max  0.8817
_exptl_absorpt_process_details   ?

_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      296(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  ?
_diffrn_measurement_method       ?
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            6998
_diffrn_reflns_av_R_equivalents  0.0235
_diffrn_reflns_av_sigmaI/netI    0.0589
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_theta_min         1.81
_diffrn_reflns_theta_max         26.14
_reflns_number_total             5168
_reflns_number_gt                3721
_reflns_threshold_expression     >2σ(I)

_computing_data_collection       'Bruker SMART'
_computing_cell_refinement       'Bruker SMART'
_computing_data_reduction        'Bruker SMART'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_molecular_graphics    XP
_computing_publication_material  WinGX

_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 > 2σ(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)+(0.0457P)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         5168
_refine_ls_number_parameters     368
_refine_ls_number_restraints     9
_refine_ls_R_factor_all          0.0714
_refine_ls_R_factor_gt           0.0459
_refine_ls_wR_factor_ref         0.1081
_refine_ls_wR_factor_gt          0.0943
_refine_ls_goodness_of_fit_ref   1.032
_refine_ls_restrained_S_all      1.032
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
Cu1 Cu 0.06873(5) 0.60692(4) 0.33158(4) 0.03174(15) Uani 1 1 d . . .
Cu2 Cu 0.34624(5) 0.57552(4) 0.64016(4) 0.03511(15) Uani 1 1 d . . .
Cl1 Cl 0.36555(12) 0.00156(10) 0.43503(11) 0.0513(3) Uani 1 1 d . . .
O1 O 0.0528(3) 0.4648(2) 0.2585(2) 0.0392(7) Uani 1 1 d . . .
O2 O 0.3137(3) 0.4593(2) 0.5433(2) 0.0388(7) Uani 1 1 d . . .
O3 O 0.2430(3) 0.7040(2) 0.5537(2) 0.0409(7) Uani 1 1 d . . .
O4 O 0.1698(3) 0.5691(3) 0.7966(3) 0.0453(7) Uani 1 1 d D . .
H4A H 0.134(4) 0.634(3) 0.839(4) 0.068 Uiso 1 1 d D . .
H4B H 0.107(3) 0.553(4) 0.779(4) 0.068 Uiso 1 1 d D . .
N1 N 0.1776(3) 0.4797(3) 0.4145(3) 0.0313(7) Uani 1 1 d . . .
N2 N 0.1159(3) 0.7179(3) 0.4212(3) 0.0311(7) Uani 1 1 d . . .
N3 N -0.0324(3) 0.7374(3) 0.2394(3) 0.0366(8) Uani 1 1 d . . .
H3 H 0.0252 0.7374 0.1671 0.044 Uiso 1 1 calc R . .
N4 N 0.4729(3) 0.4517(3) 0.7162(3) 0.0343(8) Uani 1 1 d . . .
N5 N 0.4030(3) 0.6909(3) 0.7147(3) 0.0329(8) Uani 1 1 d . . .
C1 C 0.1224(4) 0.3574(3) 0.2979(3) 0.0322(9) Uani 1 1 d . . .
C2 C 0.1925(4) 0.3587(3) 0.3842(3) 0.0284(8) Uani 1 1 d . . .
C3 C 0.2666(4) 0.2500(3) 0.4259(3) 0.0327(9) Uani 1 1 d . . .
H3A H 0.3115 0.2517 0.4829 0.039 Uiso 1 1 calc R . .
C4 C 0.2729(4) 0.1394(3) 0.3819(3) 0.0340(9) Uani 1 1 d . . .
C5 C 0.2081(4) 0.1352(4) 0.2957(4) 0.0394(10) Uani 1 1 d . . .
H5 H 0.2155 0.0596 0.2651 0.047 Uiso 1 1 calc R . .
C6 C 0.1332(4) 0.2430(4) 0.2558(4) 0.0389(10) Uani 1 1 d . . .
H6 H 0.0884 0.2396 0.1993 0.047 Uiso 1 1 calc R . .
C7 C 0.2336(4) 0.5186(3) 0.4828(3) 0.0305(9) Uani 1 1 d . . .
C8 C 0.1940(4) 0.6594(3) 0.4868(3) 0.0321(9) Uani 1 1 d . . .
C9 C 0.0722(4) 0.8538(3) 0.4229(4) 0.0389(10) Uani 1 1 d . . .
H9A H 0.1445 0.8816 0.4301 0.047 Uiso 1 1 calc R . .
H9B H -0.0022 0.8846 0.4917 0.047 Uiso 1 1 calc R . .
C10 C 0.0304(4) 0.9059(3) 0.3118(4) 0.0405(10) Uani 1 1 d . . .
H10A H 0.0002 0.9953 0.3180 0.049 Uiso 1 1 calc R . .
H10B H 0.1079 0.8817 0.2444 0.049 Uiso 1 1 calc R . .
C11 C -0.0782(4) 0.8658(4) 0.2871(4) 0.0425(10) Uani 1 1 d . . .
H11A H -0.1477 0.8727 0.3602 0.051 Uiso 1 1 calc R . .
H11B H -0.1172 0.9218 0.2304 0.051 Uiso 1 1 calc R . .
C12 C -0.1457(5) 0.7114(4) 0.2154(5) 0.0636(15) Uani 1 1 d . . .
H12A H -0.2016 0.6943 0.2887 0.095 Uiso 1 1 calc R . .
H12B H -0.1136 0.6410 0.1627 0.095 Uiso 1 1 calc R . .
H12C H -0.1963 0.7818 0.1790 0.095 Uiso 1 1 calc R . .
C13 C 0.4995(4) 0.3291(4) 0.7146(4) 0.0440(11) Uani 1 1 d . . .
H13 H 0.4650 0.2952 0.6654 0.053 Uiso 1 1 calc R . .
C14 C 0.5754(4) 0.2516(4) 0.7824(4) 0.0488(12) Uani 1 1 d . . .
H14 H 0.5909 0.1668 0.7805 0.059 Uiso 1 1 calc R . .
C15 C 0.6283(4) 0.3019(4) 0.8533(4) 0.0459(11) Uani 1 1 d . . .
H15 H 0.6813 0.2510 0.8993 0.055 Uiso 1 1 calc R . .
C16 C 0.6027(4) 0.4276(4) 0.8559(4) 0.0417(10) Uani 1 1 d . . .
H16 H 0.6382 0.4624 0.9035 0.050 Uiso 1 1 calc R . .
C17 C 0.5233(4) 0.5017(4) 0.7868(3) 0.0339(9) Uani 1 1 d . . .
C18 C 0.4850(4) 0.6380(4) 0.7851(3) 0.0322(9) Uani 1 1 d . . .
C19 C 0.5245(4) 0.7080(4) 0.8500(3) 0.0389(10) Uani 1 1 d . . .
H19 H 0.5807 0.6700 0.8986 0.047 Uiso 1 1 calc R . .
C20 C 0.4801(4) 0.8351(4) 0.8426(4) 0.0416(10) Uani 1 1 d . . .
H20 H 0.5064 0.8838 0.8855 0.050 Uiso 1 1 calc R . .
C21 C 0.3964(4) 0.8885(4) 0.7707(4) 0.0422(10) Uani 1 1 d . . .
H21 H 0.3649 0.9740 0.7646 0.051 Uiso 1 1 calc R . .
C22 C 0.3601(4) 0.8146(4) 0.7085(4) 0.0391(10) Uani 1 1 d . . .
H22 H 0.3036 0.8512 0.6598 0.047 Uiso 1 1 calc R . .
Cl2 Cl 0.11905(14) 0.77685(13) 0.96967(11) 0.0685(4) Uani 1 1 d . . .
O5 O 0.2305(4) 0.4187(3) 0.0095(3) 0.0665(10) Uani 1 1 d D . .
H5A H 0.167(4) 0.449(5) 0.070(3) 0.100 Uiso 1 1 d D . .
H5B H 0.213(6) 0.469(4) -0.045(4) 0.100 Uiso 1 1 d D . .
O6 O 0.3631(4) 0.1407(4) -0.0437(4) 0.0833(12) Uani 1 1 d D . .
H6A H 0.317(6) 0.215(2) -0.021(6) 0.125 Uiso 1 1 d D . .
H6B H 0.307(5) 0.101(5) -0.022(6) 0.125 Uiso 1 1 d D . .
O7 O 0.1653(4) 0.0243(4) 0.0340(4) 0.0836(12) Uani 1 1 d D . .
H7A H 0.091(4) 0.080(4) 0.034(6) 0.125 Uiso 1 1 d D . .
H7B H 0.161(6) -0.040(3) 0.004(6) 0.125 Uiso 1 1 d D . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Cu1 N1 1.938(3) . ?
Cu1 O1 1.966(2) . ?
Cu1 N2 1.968(3) . ?
Cu1 N3 1.985(3) . ?
Cu2 O3 1.942(3) . ?
Cu2 N5 1.967(3) . ?
Cu2 O2 1.977(2) . ?
Cu2 N4 1.979(3) . ?
Cu2 O4 2.298(3) . ?
Cl1 C4 1.748(4) . ?
O1 C1 1.341(4) . ?
O2 C7 1.266(4) . ?
O3 C8 1.271(4) . ?
O4 H4A 0.845(10) . ?
O4 H4B 0.850(10) . ?
N1 C7 1.301(4) . ?
N1 C2 1.401(4) . ?
N2 C8 1.291(4) . ?
N2 C9 1.472(4) . ?
N3 C12 1.466(5) . ?
N3 C11 1.487(5) . ?
N3 H3 0.9100 . ?
N4 C13 1.338(5) . ?
N4 C17 1.350(5) . ?
N5 C22 1.343(5) . ?
N5 C18 1.347(4) . ?
C1 C6 1.389(5) . ?
C1 C2 1.423(5) . ?
C2 C3 1.381(5) . ?
C3 C4 1.375(5) . ?
C3 H3A 0.9300 . ?
C4 C5 1.387(5) . ?
C5 C6 1.369(5) . ?
C5 H5 0.9300 . ?
C6 H6 0.9300 . ?
C7 C8 1.528(5) . ?
C9 C10 1.506(5) . ?
C9 H9A 0.9700 . ?
C9 H9B 0.9700 . ?
C10 C11 1.506(5) . ?
C10 H10A 0.9700 . ?
C10 H10B 0.9700 . ?
C11 H11A 0.9700 . ?
C11 H11B 0.9700 . ?
C12 H12A 0.9600 . ?
C12 H12B 0.9600 . ?
C12 H12C 0.9600 . ?
C13 C14 1.368(6) . ?
C13 H13 0.9300 . ?
C14 C15 1.375(6) . ?
C14 H14 0.9300 . ?
C15 C16 1.375(6) . ?
C15 H15 0.9300 . ?
C16 C17 1.386(5) . ?
C16 H16 0.9300 . ?
C17 C18 1.479(5) . ?
C18 C19 1.374(5) . ?
C19 C20 1.381(6) . ?
C19 H19 0.9300 . ?
C20 C21 1.373(5) . ?
C20 H20 0.9300 . ?
C21 C22 1.365(5) . ?
C21 H21 0.9300 . ?
C22 H22 0.9300 . ?
O5 H5A 0.849(10) . ?
O5 H5B 0.843(10) . ?
O6 H6A 0.853(10) . ?
O6 H6B 0.857(10) . ?
O7 H7A 0.854(10) . ?
O7 H7B 0.851(10) . ?

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 Cu1 O1 83.18(11) . . ?
N1 Cu1 N2 82.98(12) . . ?
O1 Cu1 N2 166.06(11) . . ?
N1 Cu1 N3 176.43(14) . . ?
O1 Cu1 N3 97.16(11) . . ?
N2 Cu1 N3 96.54(12) . . ?
O3 Cu2 N5 93.85(11) . . ?
O3 Cu2 O2 85.30(10) . . ?
N5 Cu2 O2 170.78(12) . . ?
O3 Cu2 N4 172.05(12) . . ?
N5 Cu2 N4 82.14(13) . . ?
O2 Cu2 N4 97.56(11) . . ?
O3 Cu2 O4 96.30(12) . . ?
N5 Cu2 O4 96.85(12) . . ?
O2 Cu2 O4 92.37(11) . . ?
N4 Cu2 O4 91.01(12) . . ?
C1 O1 Cu1 111.6(2) . . ?
C7 O2 Cu2 109.9(2) . . ?
C8 O3 Cu2 111.5(2) . . ?
Cu2 O4 H4A 114(3) . . ?
Cu2 O4 H4B 116(3) . . ?
H4A O4 H4B 106(4) . . ?
C7 N1 C2 129.6(3) . . ?
C7 N1 Cu1 115.7(2) . . ?
C2 N1 Cu1 114.6(2) . . ?
C8 N2 C9 118.6(3) . . ?
C8 N2 Cu1 113.0(2) . . ?
C9 N2 Cu1 128.4(2) . . ?
C12 N3 C11 108.7(3) . . ?
C12 N3 Cu1 113.6(3) . . ?
C11 N3 Cu1 116.3(2) . . ?
C12 N3 H3 105.8 . . ?
C11 N3 H3 105.8 . . ?
Cu1 N3 H3 105.8 . . ?
C13 N4 C17 119.0(3) . . ?
C13 N4 Cu2 126.8(3) . . ?
C17 N4 Cu2 113.7(3) . . ?
C22 N5 C18 118.6(3) . . ?
C22 N5 Cu2 126.2(3) . . ?
C18 N5 Cu2 115.0(2) . . ?
O1 C1 C6 123.2(3) . . ?
O1 C1 C2 119.3(3) . . ?
C6 C1 C2 117.5(3) . . ?
C3 C2 N1 127.7(3) . . ?
C3 C2 C1 121.0(3) . . ?
N1 C2 C1 111.3(3) . . ?
C4 C3 C2 119.1(3) . . ?
C4 C3 H3A 120.5 . . ?
C2 C3 H3A 120.5 . . ?
C3 C4 C5 121.2(4) . . ?
C3 C4 Cl1 119.2(3) . . ?
C5 C4 Cl1 119.5(3) . . ?
C6 C5 C4 119.6(4) . . ?
C6 C5 H5 120.2 . . ?
C4 C5 H5 120.2 . . ?
C5 C6 C1 121.6(4) . . ?
C5 C6 H6 119.2 . . ?
C1 C6 H6 119.2 . . ?
O2 C7 N1 130.7(3) . . ?
O2 C7 C8 117.0(3) . . ?
N1 C7 C8 112.3(3) . . ?
O3 C8 N2 128.2(4) . . ?
O3 C8 C7 115.8(3) . . ?
N2 C8 C7 116.0(3) . . ?
N2 C9 C10 111.6(3) . . ?
N2 C9 H9A 109.3 . . ?
C10 C9 H9A 109.3 . . ?
N2 C9 H9B 109.3 . . ?
C10 C9 H9B 109.3 . . ?
H9A C9 H9B 108.0 . . ?
C11 C10 C9 114.9(3) . . ?
C11 C10 H10A 108.5 . . ?
C9 C10 H10A 108.5 . . ?
C11 C10 H10B 108.5 . . ?
C9 C10 H10B 108.5 . . ?
H10A C10 H10B 107.5 . . ?
N3 C11 C10 114.2(3) . . ?
N3 C11 H11A 108.7 . . ?
C10 C11 H11A 108.7 . . ?
N3 C11 H11B 108.7 . . ?
C10 C11 H11B 108.7 . . ?
H11A C11 H11B 107.6 . . ?
N3 C12 H12A 109.5 . . ?
N3 C12 H12B 109.5 . . ?
H12A C12 H12B 109.5 . . ?
N3 C12 H12C 109.5 . . ?
H12A C12 H12C 109.5 . . ?
H12B C12 H12C 109.5 . . ?
N4 C13 C14 122.7(4) . . ?
N4 C13 H13 118.6 . . ?
C14 C13 H13 118.6 . . ?
C13 C14 C15 118.4(4) . . ?
C13 C14 H14 120.8 . . ?
C15 C14 H14 120.8 . . ?
C16 C15 C14 119.8(4) . . ?
C16 C15 H15 120.1 . . ?
C14 C15 H15 120.1 . . ?
C15 C16 C17 119.1(4) . . ?
C15 C16 H16 120.4 . . ?
C17 C16 H16 120.4 . . ?
N4 C17 C16 120.8(4) . . ?
N4 C17 C18 115.0(3) . . ?
C16 C17 C18 124.2(4) . . ?
N5 C18 C19 121.3(4) . . ?
N5 C18 C17 113.8(3) . . ?
C19 C18 C17 124.9(3) . . ?
C18 C19 C20 119.5(4) . . ?
C18 C19 H19 120.2 . . ?
C20 C19 H19 120.2 . . ?
C21 C20 C19 118.9(4) . . ?
C21 C20 H20 120.5 . . ?
C19 C20 H20 120.5 . . ?
C22 C21 C20 119.1(4) . . ?
C22 C21 H21 120.4 . . ?
C20 C21 H21 120.4 . . ?
N5 C22 C21 122.5(4) . . ?
N5 C22 H22 118.8 . . ?
C21 C22 H22 118.8 . . ?
H5A O5 H5B 104(5) . . ?
H6A O6 H6B 104(6) . . ?
H7A O7 H7B 104(2) . . ?

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 Cu1 O1 C1 -1.0(3) . . . . ?
N2 Cu1 O1 C1 5.9(7) . . . . ?
N3 Cu1 O1 C1 175.4(3) . . . . ?
O3 Cu2 O2 C7 -6.7(3) . . . . ?
N5 Cu2 O2 C7 -91.8(7) . . . . ?
N4 Cu2 O2 C7 -179.3(3) . . . . ?
O4 Cu2 O2 C7 89.4(3) . . . . ?
N5 Cu2 O3 C8 176.6(3) . . . . ?
O2 Cu2 O3 C8 5.8(3) . . . . ?
N4 Cu2 O3 C8 117.2(8) . . . . ?
O4 Cu2 O3 C8 -86.1(3) . . . . ?
O1 Cu1 N1 C7 175.8(3) . . . . ?
N2 Cu1 N1 C7 -2.5(3) . . . . ?
N3 Cu1 N1 C7 80(2) . . . . ?
O1 Cu1 N1 C2 0.6(3) . . . . ?
N2 Cu1 N1 C2 -177.7(3) . . . . ?
N3 Cu1 N1 C2 -95(2) . . . . ?
N1 Cu1 N2 C8 1.3(3) . . . . ?
O1 Cu1 N2 C8 -5.6(7) . . . . ?
N3 Cu1 N2 C8 -175.1(3) . . . . ?
N1 Cu1 N2 C9 -177.6(3) . . . . ?
O1 Cu1 N2 C9 175.4(4) . . . . ?
N3 Cu1 N2 C9 6.0(3) . . . . ?
N1 Cu1 N3 C12 132.0(19) . . . . ?
O1 Cu1 N3 C12 36.7(3) . . . . ?
N2 Cu1 N3 C12 -145.9(3) . . . . ?
N1 Cu1 N3 C11 -101(2) . . . . ?
O1 Cu1 N3 C11 164.1(3) . . . . ?
N2 Cu1 N3 C11 -18.5(3) . . . . ?
O3 Cu2 N4 C13 -122.0(8) . . . . ?
N5 Cu2 N4 C13 177.9(4) . . . . ?
O2 Cu2 N4 C13 -11.4(4) . . . . ?
O4 Cu2 N4 C13 81.1(3) . . . . ?
O3 Cu2 N4 C17 65.9(9) . . . . ?
N5 Cu2 N4 C17 5.8(3) . . . . ?
O2 Cu2 N4 C17 176.5(3) . . . . ?
O4 Cu2 N4 C17 -90.9(3) . . . . ?
O3 Cu2 N5 C22 6.9(3) . . . . ?
O2 Cu2 N5 C22 91.3(8) . . . . ?
N4 Cu2 N5 C22 -180.0(3) . . . . ?
O4 Cu2 N5 C22 -89.9(3) . . . . ?
O3 Cu2 N5 C18 -178.3(3) . . . . ?
O2 Cu2 N5 C18 -93.9(8) . . . . ?
N4 Cu2 N5 C18 -5.2(3) . . . . ?
O4 Cu2 N5 C18 84.9(3) . . . . ?
Cu1 O1 C1 C6 -176.7(3) . . . . ?
Cu1 O1 C1 C2 1.3(4) . . . . ?
C7 N1 C2 C3 3.8(7) . . . . ?
Cu1 N1 C2 C3 178.2(3) . . . . ?
C7 N1 C2 C1 -174.5(4) . . . . ?
Cu1 N1 C2 C1 -0.1(4) . . . . ?
O1 C1 C2 C3 -179.2(3) . . . . ?
C6 C1 C2 C3 -1.1(6) . . . . ?
O1 C1 C2 N1 -0.8(5) . . . . ?
C6 C1 C2 N1 177.3(3) . . . . ?
N1 C2 C3 C4 -177.6(4) . . . . ?
C1 C2 C3 C4 0.6(6) . . . . ?
C2 C3 C4 C5 1.0(6) . . . . ?
C2 C3 C4 Cl1 -179.6(3) . . . . ?
C3 C4 C5 C6 -1.9(6) . . . . ?
Cl1 C4 C5 C6 178.6(3) . . . . ?
C4 C5 C6 C1 1.4(6) . . . . ?
O1 C1 C6 C5 178.2(4) . . . . ?
C2 C1 C6 C5 0.1(6) . . . . ?
Cu2 O2 C7 N1 -174.3(4) . . . . ?
Cu2 O2 C7 C8 6.4(4) . . . . ?
C2 N1 C7 O2 -2.1(7) . . . . ?
Cu1 N1 C7 O2 -176.4(3) . . . . ?
C2 N1 C7 C8 177.3(3) . . . . ?
Cu1 N1 C7 C8 2.9(4) . . . . ?
Cu2 O3 C8 N2 176.7(3) . . . . ?
Cu2 O3 C8 C7 -3.9(4) . . . . ?
C9 N2 C8 O3 -1.8(6) . . . . ?
Cu1 N2 C8 O3 179.2(3) . . . . ?
C9 N2 C8 C7 178.9(3) . . . . ?
Cu1 N2 C8 C7 -0.2(4) . . . . ?
O2 C7 C8 O3 -1.8(5) . . . . ?
N1 C7 C8 O3 178.8(3) . . . . ?
O2 C7 C8 N2 177.6(3) . . . . ?
N1 C7 C8 N2 -1.8(5) . . . . ?
C8 N2 C9 C10 157.3(4) . . . . ?
Cu1 N2 C9 C10 -23.8(5) . . . . ?
N2 C9 C10 C11 56.7(5) . . . . ?
C12 N3 C11 C10 -178.1(4) . . . . ?
Cu1 N3 C11 C10 52.1(4) . . . . ?
C9 C10 C11 N3 -76.0(5) . . . . ?
C17 N4 C13 C14 0.4(6) . . . . ?
Cu2 N4 C13 C14 -171.2(3) . . . . ?
N4 C13 C14 C15 -1.2(7) . . . . ?
C13 C14 C15 C16 0.9(7) . . . . ?
C14 C15 C16 C17 0.1(6) . . . . ?
C13 N4 C17 C16 0.7(6) . . . . ?
Cu2 N4 C17 C16 173.4(3) . . . . ?
C13 N4 C17 C18 -178.2(3) . . . . ?
Cu2 N4 C17 C18 -5.5(4) . . . . ?
C15 C16 C17 N4 -0.9(6) . . . . ?
C15 C16 C17 C18 177.9(4) . . . . ?
C22 N5 C18 C19 0.2(6) . . . . ?
Cu2 N5 C18 C19 -175.0(3) . . . . ?
C22 N5 C18 C17 178.8(3) . . . . ?
Cu2 N5 C18 C17 3.6(4) . . . . ?
N4 C17 C18 N5 1.3(5) . . . . ?
C16 C17 C18 N5 -177.5(4) . . . . ?
N4 C17 C18 C19 179.8(4) . . . . ?
C16 C17 C18 C19 1.0(6) . . . . ?
N5 C18 C19 C20 -0.5(6) . . . . ?
C17 C18 C19 C20 -178.8(4) . . . . ?
C18 C19 C20 C21 0.5(6) . . . . ?
C19 C20 C21 C22 -0.3(6) . . . . ?
C18 N5 C22 C21 -0.1(6) . . . . ?
Cu2 N5 C22 C21 174.6(3) . . . . ?
C20 C21 C22 N5 0.1(7) . . . . ?

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
N3 H3 Cl2 0.91 2.34 3.221(4) 163.8 1_554
O4 H4A Cl2 0.845(10) 2.25(2) 3.045(3) 156(4) .
O4 H4B O1 0.850(10) 1.983(12) 2.829(4) 174(4) 2_566
O5 H5A O1 0.849(10) 2.21(3) 3.010(5) 157(5) .
O5 H5B O4 0.843(10) 2.183(16) 3.014(5) 169(6) 1_554
O6 H6A O5 0.853(10) 2.232(19) 3.071(6) 168(7) .
O6 H6B O7 0.857(10) 1.969(14) 2.823(6) 175(7) .
O7 H7A Cl2 0.854(10) 2.364(12) 3.217(4) 177(5) 2_566
O7 H7B Cl2 0.851(10) 2.37(2) 3.207(4) 166(6) 1_544
C19 H19 O5 0.93 2.47 3.385(5) 166.7 2_666

_diffrn_measured_fraction_theta_max 0.969
_diffrn_reflns_theta_full        26.14
_diffrn_measured_fraction_theta_full 0.969
_refine_diff_density_max         0.419
_refine_diff_density_min         -0.378
_refine_diff_density_rms         0.085
_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: ethanol'
