# Electronic Supplementary Material (ESI) for New Journal of Chemistry.
# This journal is © The Royal Society of Chemistry and the Centre National de la Recherche Scientifique 2016

####################################################################### 
# 
# 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_shelx
_database_code_depnum_ccdc_archive 'CCDC 1038855'
_audit_update_record             
;
2016-05-05 deposited with the CCDC.
2016-05-18 downloaded from the CCDC.
;

# start Validation Reply Form
_vrf_PLAT430_I                   
;
PROBLEM: Short Inter D...A Contact  O1M    ..  O1M     ..       1.83 Ang.  
RESPONSE: This is a disordered oxygen (occupancy 0.5)
;
# end Validation Reply Form

_audit_creation_method           SHELXL-2014/6
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C20 H35 Cl Cu2 N2 O6, 2(Cl O4), C H4 O'
_chemical_formula_sum            'C21 H39 Cl3 Cu2 N2 O15'
_chemical_formula_weight         792.97

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'
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'
N N 0.0061 0.0033 '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'

_space_group_crystal_system      orthorhombic
_space_group_IT_number           60
_space_group_name_H-M_alt        'P b c n'
_space_group_name_Hall           '-P 2n 2ab'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;

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

_cell_length_a                   11.5500(8)
_cell_length_b                   29.977(2)
_cell_length_c                   9.1440(10)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     3166.0(5)
_cell_formula_units_Z            4
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    886
_cell_measurement_theta_min      2.20
_cell_measurement_theta_max      22.60

_exptl_crystal_description       plate
_exptl_crystal_colour            'deep green'
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.664
_exptl_crystal_F_000             1632
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.30
_exptl_crystal_size_mid          0.28
_exptl_crystal_size_min          0.11
_exptl_absorpt_coefficient_mu    1.666
_exptl_absorpt_correction_type   MULTI-SCAN
_exptl_absorpt_correction_T_min  0.555
_exptl_absorpt_correction_T_max  0.710
_exptl_absorpt_process_details   'BRUKER SADABS'

_exptl_absorpt_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 SMART APEX CCD DIFFRACTOMETER'
_diffrn_measurement_method       'OMEGA-PHI SCAN'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            9871
_diffrn_reflns_av_unetI/netI     0.0405
_diffrn_reflns_av_R_equivalents  0.0360
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_k_min       -37
_diffrn_reflns_limit_k_max       32
_diffrn_reflns_limit_l_min       -4
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_theta_min         2.921
_diffrn_reflns_theta_max         26.369
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measured_fraction_theta_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_point_group_measured_fraction_full 0.998
_reflns_number_total             3242
_reflns_number_gt                2279
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;

_computing_data_collection       'BRUKER SMART'
_computing_cell_refinement       'BRUKER SMART'
_computing_data_reduction        'BRUKER SAINT'
_computing_structure_solution    'SHELX97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-2014/6 (Sheldrick, 2014)'
_computing_molecular_graphics    'Ortep3 for Windows (Farrugia,1997)'
_computing_publication_material  'Wingx 2013.03 (Farrugia, 2012)'

_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.1382P)²+4.8212P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         3242
_refine_ls_number_parameters     224
_refine_ls_number_restraints     22
_refine_ls_R_factor_all          0.1017
_refine_ls_R_factor_gt           0.0770
_refine_ls_wR_factor_ref         0.2468
_refine_ls_wR_factor_gt          0.2234
_refine_ls_goodness_of_fit_ref   1.056
_refine_ls_restrained_S_all      1.115
_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_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Cu Cu 0.12518(6) 0.12558(2) 0.22849(10) 0.0510(3) Uani 1 1 d . . . . .
N1 N 0.2441(4) 0.07813(14) 0.2097(6) 0.0442(11) Uani 1 1 d . . . . .
Cl1 Cl 0.0000 -0.11056(10) 0.2500 0.137(2) Uani 1 2 d S T P . .
O1 O 0.0000 0.0834(2) 0.2500 0.070(2) Uani 1 2 d S T P . .
O2 O 0.0000 0.1657(2) 0.2500 0.073(2) Uani 1 2 d DS T P . .
H22 H 0.0000 0.1940(7) 0.2500 0.109 Uiso 1 2 d DS U P . .
O3 O 0.2255(4) 0.15878(14) 0.0810(6) 0.0687(13) Uani 1 1 d . . . . .
O4 O 0.2039(5) 0.13359(18) 0.4408(6) 0.0783(15) Uani 1 1 d . . . . .
C1 C 0.0000 0.0389(3) 0.2500 0.0474(19) Uani 1 2 d S T P . .
C2 C 0.0972(5) 0.01540(19) 0.1979(7) 0.0497(14) Uani 1 1 d . . . . .
C3 C 0.0973(6) -0.0303(2) 0.2035(8) 0.0573(17) Uani 1 1 d . . . . .
H3 H 0.1626 -0.0464 0.1761 0.069 Uiso 1 1 calc R U . . .
C4 C 0.0000 -0.0517(3) 0.2500 0.066(3) Uani 1 2 d S T P . .
C5 C 0.2002(5) 0.03946(19) 0.1282(8) 0.0539(15) Uani 1 1 d . . . . .
H5A H 0.2628 0.0182 0.1166 0.065 Uiso 1 1 calc R U . . .
H5B H 0.1776 0.0493 0.0313 0.065 Uiso 1 1 calc R U . . .
C6 C 0.3452(5) 0.0975(2) 0.1262(9) 0.0609(17) Uani 1 1 d . . . . .
H6A H 0.3958 0.1135 0.1929 0.073 Uiso 1 1 calc R U . . .
H6B H 0.3894 0.0737 0.0812 0.073 Uiso 1 1 calc R U . . .
C7 C 0.3020(6) 0.1287(2) 0.0106(8) 0.0624(18) Uani 1 1 d . . . . .
H7A H 0.3660 0.1448 -0.0335 0.075 Uiso 1 1 calc R U . . .
H7B H 0.2617 0.1123 -0.0654 0.075 Uiso 1 1 calc R U . . .
C8 C 0.1883(8) 0.1955(3) -0.0068(12) 0.104(3) Uani 1 1 d . . . . .
H8A H 0.1296 0.1857 -0.0738 0.156 Uiso 1 1 calc R U . . .
H8B H 0.2530 0.2072 -0.0606 0.156 Uiso 1 1 calc R U . . .
H8C H 0.1572 0.2185 0.0551 0.156 Uiso 1 1 calc R U . . .
C9 C 0.2814(6) 0.0653(2) 0.3595(8) 0.0654(18) Uani 1 1 d . . . . .
H9A H 0.3513 0.0474 0.3539 0.078 Uiso 1 1 calc R U . . .
H9B H 0.2216 0.0474 0.4053 0.078 Uiso 1 1 calc R U . . .
C10 C 0.3042(6) 0.1068(2) 0.4520(9) 0.071(2) Uani 1 1 d . . . . .
H10A H 0.3182 0.0986 0.5531 0.085 Uiso 1 1 calc R U . . .
H10B H 0.3713 0.1228 0.4156 0.085 Uiso 1 1 calc R U . . .
C11 C 0.2090(9) 0.1738(3) 0.5232(12) 0.110(3) Uani 1 1 d . . . . .
H11A H 0.2476 0.1964 0.4670 0.164 Uiso 1 1 calc R U . . .
H11B H 0.2510 0.1686 0.6122 0.164 Uiso 1 1 calc R U . . .
H11C H 0.1319 0.1835 0.5460 0.164 Uiso 1 1 calc R U . . .
Cl3 Cl 0.5000 0.22390(10) 0.2500 0.0884(10) Uani 1 2 d S T P . .
O9 O 0.4889(7) 0.1977(4) 0.3740(14) 0.187(5) Uani 1 1 d . . . . .
O10 O 0.5908(17) 0.2488(5) 0.2735(13) 0.313(13) Uani 1 1 d . . . . .
Cl2 Cl 0.5000 0.04760(9) 0.7500 0.0616(6) Uani 1 2 d DS T P . .
O5 O 0.5000 0.0939(4) 0.7500 0.191(8) Uani 1 2 d DS T P . .
O6 O 0.6210(9) 0.0424(5) 0.709(2) 0.117(5) Uani 0.5 1 d D . P . .
O7 O 0.4389(17) 0.0285(6) 0.646(2) 0.150(9) Uani 0.5 1 d D . P . .
O8 O 0.492(3) 0.0308(7) 0.8832(18) 0.30(3) Uani 0.5 1 d D . P . .
C1M C 0.023(6) 0.2863(10) 0.258(8) 0.124(18) Uani 0.5 1 d . . P . .
O1M O 0.0273(14) 0.2544(5) 0.344(2) 0.116(5) Uani 0.5 1 d . . P . .


_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
Cu O2 1.891(4) . ?
Cu O1 1.930(4) . ?
Cu N1 1.985(4) . ?
Cu O3 2.038(4) . ?
Cu O4 2.157(5) . ?
Cu Cu 2.9183(13) 4 ?
N1 C5 1.468(7) . ?
N1 C9 1.487(9) . ?
N1 C6 1.511(7) . ?
Cl1 C4 1.764(9) . ?
O1 C1 1.334(10) . ?
O1 Cu 1.930(4) 4 ?
O2 Cu 1.891(4) 4 ?
O2 H22 0.85(2) . ?
O3 C7 1.417(7) . ?
O3 C8 1.430(8) . ?
O4 C10 1.413(9) . ?
O4 C11 1.421(9) . ?
C1 C2 1.409(7) 4 ?
C1 C2 1.409(7) . ?
C2 C3 1.372(8) . ?
C2 C5 1.530(8) . ?
C3 C4 1.361(8) . ?
C3 H3 0.9300 . ?
C4 C3 1.361(8) 4 ?
C5 H5A 0.9700 . ?
C5 H5B 0.9700 . ?
C6 C7 1.497(10) . ?
C6 H6A 0.9700 . ?
C6 H6B 0.9700 . ?
C7 H7A 0.9700 . ?
C7 H7B 0.9700 . ?
C8 H8A 0.9600 . ?
C8 H8B 0.9600 . ?
C8 H8C 0.9600 . ?
C9 C10 1.529(10) . ?
C9 H9A 0.9700 . ?
C9 H9B 0.9700 . ?
C10 H10A 0.9700 . ?
C10 H10B 0.9700 . ?
C11 H11A 0.9600 . ?
C11 H11B 0.9600 . ?
C11 H11C 0.9600 . ?
Cl3 O10 1.305(12) . ?
Cl3 O10 1.306(12) 4_655 ?
Cl3 O9 1.386(9) 4_655 ?
Cl3 O9 1.386(9) . ?
Cl2 O7 1.313(11) . ?
Cl2 O7 1.313(11) 4_656 ?
Cl2 O8 1.321(13) 4_656 ?
Cl2 O8 1.321(13) . ?
Cl2 O5 1.389(12) . ?
Cl2 O6 1.455(9) 4_656 ?
Cl2 O6 1.455(9) . ?
C1M O1M 1.46(4) 4 ?

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
O2 Cu O1 80.4(2) . . ?
O2 Cu N1 173.7(2) . . ?
O1 Cu N1 93.3(2) . . ?
O2 Cu O3 101.12(18) . . ?
O1 Cu O3 144.40(16) . . ?
N1 Cu O3 84.22(18) . . ?
O2 Cu O4 99.09(15) . . ?
O1 Cu O4 107.27(15) . . ?
N1 Cu O4 82.3(2) . . ?
O3 Cu O4 107.6(2) . . ?
O2 Cu Cu 39.49(16) . 4 ?
O1 Cu Cu 40.89(14) . 4 ?
N1 Cu Cu 134.22(13) . 4 ?
O3 Cu Cu 130.73(14) . 4 ?
O4 Cu Cu 107.24(15) . 4 ?
C5 N1 C9 111.3(4) . . ?
C5 N1 C6 108.3(5) . . ?
C9 N1 C6 110.0(5) . . ?
C5 N1 Cu 111.7(3) . . ?
C9 N1 Cu 107.8(4) . . ?
C6 N1 Cu 107.6(3) . . ?
C1 O1 Cu 130.89(14) . 4 ?
C1 O1 Cu 130.90(14) . . ?
Cu O1 Cu 98.2(3) 4 . ?
Cu O2 Cu 101.0(3) . 4 ?
Cu O2 H22 129.49(16) . . ?
Cu O2 H22 129.49(16) 4 . ?
C7 O3 C8 115.0(6) . . ?
C7 O3 Cu 110.1(4) . . ?
C8 O3 Cu 125.3(4) . . ?
C10 O4 C11 114.1(6) . . ?
C10 O4 Cu 110.4(4) . . ?
C11 O4 Cu 126.1(6) . . ?
O1 C1 C2 120.0(4) . 4 ?
O1 C1 C2 120.0(4) . . ?
C2 C1 C2 119.9(7) 4 . ?
C3 C2 C1 119.2(6) . . ?
C3 C2 C5 119.1(5) . . ?
C1 C2 C5 121.6(5) . . ?
C4 C3 C2 118.8(6) . . ?
C4 C3 H3 120.6 . . ?
C2 C3 H3 120.6 . . ?
C3 C4 C3 123.8(8) . 4 ?
C3 C4 Cl1 118.1(4) . . ?
C3 C4 Cl1 118.1(4) 4 . ?
N1 C5 C2 115.4(5) . . ?
N1 C5 H5A 108.4 . . ?
C2 C5 H5A 108.4 . . ?
N1 C5 H5B 108.4 . . ?
C2 C5 H5B 108.4 . . ?
H5A C5 H5B 107.5 . . ?
C7 C6 N1 109.8(5) . . ?
C7 C6 H6A 109.7 . . ?
N1 C6 H6A 109.7 . . ?
C7 C6 H6B 109.7 . . ?
N1 C6 H6B 109.7 . . ?
H6A C6 H6B 108.2 . . ?
O3 C7 C6 106.5(6) . . ?
O3 C7 H7A 110.4 . . ?
C6 C7 H7A 110.4 . . ?
O3 C7 H7B 110.4 . . ?
C6 C7 H7B 110.4 . . ?
H7A C7 H7B 108.6 . . ?
O3 C8 H8A 109.5 . . ?
O3 C8 H8B 109.5 . . ?
H8A C8 H8B 109.5 . . ?
O3 C8 H8C 109.5 . . ?
H8A C8 H8C 109.5 . . ?
H8B C8 H8C 109.5 . . ?
N1 C9 C10 110.4(5) . . ?
N1 C9 H9A 109.6 . . ?
C10 C9 H9A 109.6 . . ?
N1 C9 H9B 109.6 . . ?
C10 C9 H9B 109.6 . . ?
H9A C9 H9B 108.1 . . ?
O4 C10 C9 106.3(5) . . ?
O4 C10 H10A 110.5 . . ?
C9 C10 H10A 110.5 . . ?
O4 C10 H10B 110.5 . . ?
C9 C10 H10B 110.5 . . ?
H10A C10 H10B 108.7 . . ?
O4 C11 H11A 109.5 . . ?
O4 C11 H11B 109.5 . . ?
H11A C11 H11B 109.5 . . ?
O4 C11 H11C 109.5 . . ?
H11A C11 H11C 109.5 . . ?
H11B C11 H11C 109.5 . . ?
O10 Cl3 O10 110.1(19) . 4_655 ?
O10 Cl3 O9 112.7(9) . 4_655 ?
O10 Cl3 O9 105.4(7) 4_655 4_655 ?
O10 Cl3 O9 105.4(7) . . ?
O10 Cl3 O9 112.7(9) 4_655 . ?
O9 Cl3 O9 110.9(13) 4_655 . ?
O7 Cl2 O7 128.3(17) . 4_656 ?
O7 Cl2 O8 37.3(11) . 4_656 ?
O7 Cl2 O8 117.6(10) 4_656 4_656 ?
O7 Cl2 O8 117.6(10) . . ?
O7 Cl2 O8 37.3(11) 4_656 . ?
O8 Cl2 O8 135(2) 4_656 . ?
O7 Cl2 O5 115.8(9) . . ?
O7 Cl2 O5 115.8(9) 4_656 . ?
O8 Cl2 O5 112.4(11) 4_656 . ?
O8 Cl2 O5 112.4(11) . . ?
O7 Cl2 O6 67.8(9) . 4_656 ?
O7 Cl2 O6 106.5(8) 4_656 4_656 ?
O8 Cl2 O6 105.1(9) 4_656 4_656 ?
O8 Cl2 O6 70.0(10) . 4_656 ?
O5 Cl2 O6 96.2(6) . 4_656 ?
O7 Cl2 O6 106.5(8) . . ?
O7 Cl2 O6 67.8(9) 4_656 . ?
O8 Cl2 O6 70.0(10) 4_656 . ?
O8 Cl2 O6 105.1(9) . . ?
O5 Cl2 O6 96.2(6) . . ?
O6 Cl2 O6 167.6(12) 4_656 . ?

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 Cu O2 Cu 0.0 . . . 4 ?
O3 Cu O2 Cu 143.82(17) . . . 4 ?
O4 Cu O2 Cu -106.13(15) . . . 4 ?
Cu O1 C1 C2 -15.2(3) 4 . . 4 ?
Cu O1 C1 C2 164.8(3) . . . 4 ?
Cu O1 C1 C2 164.8(3) 4 . . . ?
Cu O1 C1 C2 -15.2(3) . . . . ?
O1 C1 C2 C3 177.7(5) . . . . ?
C2 C1 C2 C3 -2.3(5) 4 . . . ?
O1 C1 C2 C5 -5.4(7) . . . . ?
C2 C1 C2 C5 174.6(7) 4 . . . ?
C1 C2 C3 C4 4.5(9) . . . . ?
C5 C2 C3 C4 -172.5(5) . . . . ?
C2 C3 C4 C3 -2.3(5) . . . 4 ?
C2 C3 C4 Cl1 177.7(5) . . . . ?
C9 N1 C5 C2 58.7(6) . . . . ?
C6 N1 C5 C2 179.7(5) . . . . ?
Cu N1 C5 C2 -61.9(6) . . . . ?
C3 C2 C5 N1 -135.3(6) . . . . ?
C1 C2 C5 N1 47.8(8) . . . . ?
C5 N1 C6 C7 84.4(6) . . . . ?
C9 N1 C6 C7 -153.8(6) . . . . ?
Cu N1 C6 C7 -36.6(6) . . . . ?
C8 O3 C7 C6 171.0(6) . . . . ?
Cu O3 C7 C6 -40.8(6) . . . . ?
N1 C6 C7 O3 51.4(7) . . . . ?
C5 N1 C9 C10 -168.9(5) . . . . ?
C6 N1 C9 C10 71.0(7) . . . . ?
Cu N1 C9 C10 -46.0(6) . . . . ?
C11 O4 C10 C9 178.9(7) . . . . ?
Cu O4 C10 C9 -32.5(6) . . . . ?
N1 C9 C10 O4 52.4(7) . . . . ?

_refine_diff_density_max         1.137
_refine_diff_density_min         -0.479
_refine_diff_density_rms         0.117

_shelxl_version_number           2014/6

####################################################################### 
# 
# 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_2
_database_code_depnum_ccdc_archive 'CCDC 1038856'
_audit_update_record             
;
2016-05-05 deposited with the CCDC.
2016-05-18 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/6
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C26 H38 Cl2 Cu2 N2 O6, 2(Cl O4), H2 O'
_chemical_formula_sum            'C26 H40 Cl4 Cu2 N2 O15'
_chemical_formula_weight         889.48

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'

_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;

loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   9.7971(4)
_cell_length_b                   11.2747(4)
_cell_length_c                   18.5531(9)
_cell_angle_alpha                97.974(2)
_cell_angle_beta                 92.990(2)
_cell_angle_gamma                114.8160(10)
_cell_volume                     1828.20(13)
_cell_formula_units_Z            2
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    2406
_cell_measurement_theta_min      2.23
_cell_measurement_theta_max      28.50

_exptl_crystal_description       rectangular
_exptl_crystal_colour            'deep green'
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.616
_exptl_crystal_F_000             912
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.36
_exptl_crystal_size_mid          0.28
_exptl_crystal_size_min          0.12
_exptl_absorpt_coefficient_mu    1.523
_exptl_absorpt_correction_type   MULTI-SCAN
_exptl_absorpt_correction_T_min  0.558
_exptl_absorpt_correction_T_max  0.750
_exptl_absorpt_process_details   'BRUKER SADABS'

_exptl_absorpt_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 SMART APEX CCD DIFFRACTOMETER'
_diffrn_measurement_method       'OMEGA-PHI SCAN'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            24997
_diffrn_reflns_av_unetI/netI     0.0351
_diffrn_reflns_av_R_equivalents  0.0266
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_l_min       -26
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_theta_min         1.117
_diffrn_reflns_theta_max         30.557
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.886
_diffrn_measured_fraction_theta_full 0.988
_diffrn_reflns_Laue_measured_fraction_max 0.886
_diffrn_reflns_Laue_measured_fraction_full 0.988
_diffrn_reflns_point_group_measured_fraction_max 0.886
_diffrn_reflns_point_group_measured_fraction_full 0.988
_reflns_number_total             9925
_reflns_number_gt                7071
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;

_computing_data_collection       'BRUKER SMART'
_computing_cell_refinement       'BRUKER SMART'
_computing_data_reduction        'BRUKER SAINT'
_computing_structure_solution    'SHELX97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-2014/6 (Sheldrick, 2014)'
_computing_molecular_graphics    'Ortep3 for Windows (Farrugia,1997)'
_computing_publication_material  'Wingx 2013.03 (Farrugia, 2012)'

_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.1103P)²+1.3000P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         9925
_refine_ls_number_parameters     473
_refine_ls_number_restraints     49
_refine_ls_R_factor_all          0.0804
_refine_ls_R_factor_gt           0.0583
_refine_ls_wR_factor_ref         0.1934
_refine_ls_wR_factor_gt          0.1771
_refine_ls_goodness_of_fit_ref   1.040
_refine_ls_restrained_S_all      1.072
_refine_ls_shift/su_max          0.004
_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_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Cu1 Cu 0.18320(4) 0.19345(4) 0.31727(2) 0.04165(13) Uani 1 1 d . . . . .
Cu2 Cu 0.27571(5) 0.34733(4) 0.19712(2) 0.04407(14) Uani 1 1 d . . . . .
Cl1 Cl -0.52165(12) -0.08177(13) 0.08701(6) 0.0682(3) Uani 1 1 d . . . . .
Cl2 Cl 1.00647(14) 0.50650(18) 0.39234(9) 0.0978(5) Uani 1 1 d . . . . .
N1 N -0.0115(3) 0.0625(3) 0.34037(15) 0.0401(6) Uani 1 1 d . . . . .
N2 N 0.4736(4) 0.4482(3) 0.16424(17) 0.0498(7) Uani 1 1 d . . . . .
O1 O 0.0925(3) 0.2502(3) 0.23708(14) 0.0499(6) Uani 1 1 d . . . . .
O2 O 0.3630(3) 0.3219(3) 0.28941(15) 0.0548(6) Uani 1 1 d . . . . .
O3 O 0.2084(3) 0.0183(3) 0.27854(18) 0.0646(8) Uani 1 1 d . . . . .
O4 O 0.2179(3) 0.2705(3) 0.42710(13) 0.0544(6) Uani 1 1 d . . . . .
O5 O 0.2832(3) 0.1885(3) 0.11925(17) 0.0652(8) Uani 1 1 d . . . . .
O6 O 0.2192(4) 0.4851(3) 0.16432(18) 0.0679(8) Uani 1 1 d . . . . .
C1 C -0.0510(4) 0.1802(4) 0.2027(2) 0.0466(8) Uani 1 1 d . . . . .
C2 C -0.0883(5) 0.1839(4) 0.1300(2) 0.0553(9) Uani 1 1 d . . . . .
H2 H -0.0147 0.2388 0.1047 0.066 Uiso 1 1 calc R U . . .
C3 C -0.2329(5) 0.1071(5) 0.0948(2) 0.0571(9) Uani 1 1 d . . . . .
H3 H -0.2569 0.1109 0.0463 0.068 Uiso 1 1 calc R U . . .
C4 C -0.3419(4) 0.0246(4) 0.1319(2) 0.0528(9) Uani 1 1 d . . . . .
C5 C -0.3089(4) 0.0222(4) 0.2048(2) 0.0494(8) Uani 1 1 d . . . . .
H5 H -0.3835 -0.0331 0.2295 0.059 Uiso 1 1 calc R U . . .
C6 C -0.1642(4) 0.1022(4) 0.24156(19) 0.0455(7) Uani 1 1 d . . . . .
C7 C -0.1333(4) 0.1051(4) 0.32169(18) 0.0449(7) Uani 1 1 d . . . . .
H7A H -0.2261 0.0473 0.3387 0.054 Uiso 1 1 calc R U . . .
H7B H -0.1038 0.1946 0.3478 0.054 Uiso 1 1 calc R U . . .
C8 C -0.0457(5) -0.0717(4) 0.2990(2) 0.0534(9) Uani 1 1 d . . . . .
H8A H -0.0869 -0.0797 0.2490 0.064 Uiso 1 1 calc R U . . .
H8B H -0.1217 -0.1385 0.3213 0.064 Uiso 1 1 calc R U . . .
C9 C 0.0925(5) -0.0958(4) 0.2985(2) 0.0608(10) Uani 1 1 d . . . . .
H9A H 0.1222 -0.1080 0.3466 0.073 Uiso 1 1 calc R U . . .
H9B H 0.0737 -0.1747 0.2633 0.073 Uiso 1 1 calc R U . . .
C10 C 0.3363(7) 0.0005(6) 0.2563(3) 0.0853(16) Uani 1 1 d . . . . .
H10A H 0.3878 -0.0141 0.2972 0.128 Uiso 1 1 calc R U . . .
H10B H 0.4040 0.0785 0.2393 0.128 Uiso 1 1 calc R U . . .
H10C H 0.3034 -0.0748 0.2174 0.128 Uiso 1 1 calc R U . . .
C11 C 0.0085(4) 0.0638(4) 0.42053(18) 0.0480(8) Uani 1 1 d . . . . .
H11A H 0.0680 0.0162 0.4304 0.058 Uiso 1 1 calc R U . . .
H11B H -0.0898 0.0189 0.4370 0.058 Uiso 1 1 calc R U . . .
C12 C 0.0872(4) 0.2047(4) 0.46242(19) 0.0528(9) Uani 1 1 d . . . . .
H12A H 0.0206 0.2485 0.4609 0.063 Uiso 1 1 calc R U . . .
H12B H 0.1166 0.2054 0.5133 0.063 Uiso 1 1 calc R U . . .
C13 C 0.3049(5) 0.4054(5) 0.4620(3) 0.0699(12) Uani 1 1 d . . . . .
H13A H 0.2412 0.4510 0.4644 0.105 Uiso 1 1 calc R U . . .
H13B H 0.3865 0.4480 0.4343 0.105 Uiso 1 1 calc R U . . .
H13C H 0.3455 0.4081 0.5107 0.105 Uiso 1 1 calc R U . . .
C21 C 0.5122(4) 0.3641(4) 0.31348(19) 0.0460(7) Uani 1 1 d . . . . .
C22 C 0.5560(5) 0.3084(4) 0.3669(2) 0.0556(9) Uani 1 1 d . . . . .
H22 H 0.4828 0.2408 0.3861 0.067 Uiso 1 1 calc R U . . .
C23 C 0.7074(5) 0.3524(5) 0.3921(2) 0.0602(10) Uani 1 1 d . . . . .
H23 H 0.7366 0.3164 0.4288 0.072 Uiso 1 1 calc R U . . .
C24 C 0.8144(5) 0.4503(5) 0.3617(2) 0.0617(10) Uani 1 1 d . . . . .
C25 C 0.7731(4) 0.5060(4) 0.3089(2) 0.0574(10) Uani 1 1 d . . . . .
H25 H 0.8478 0.5718 0.2894 0.069 Uiso 1 1 calc R U . . .
C26 C 0.6214(4) 0.4661(4) 0.2837(2) 0.0496(8) Uani 1 1 d . . . . .
C27 C 0.5808(5) 0.5364(4) 0.2295(2) 0.0584(9) Uani 1 1 d . . . . .
H27A H 0.5365 0.5906 0.2544 0.070 Uiso 1 1 calc R U . . .
H27B H 0.6732 0.5957 0.2128 0.070 Uiso 1 1 calc R U . . .
C28 C 0.5297(5) 0.3555(5) 0.1268(2) 0.0620(10) Uani 1 1 d . . . . .
H28A H 0.5728 0.3230 0.1634 0.074 Uiso 1 1 calc R U . . .
H28B H 0.6094 0.4028 0.0985 0.074 Uiso 1 1 calc R U . . .
C29 C 0.4055(6) 0.2398(5) 0.0769(3) 0.0696(12) Uani 1 1 d . . . . .
H29A H 0.3743 0.2685 0.0346 0.083 Uiso 1 1 calc R U . . .
H29B H 0.4396 0.1727 0.0600 0.083 Uiso 1 1 calc R U . . .
C30 C 0.1660(6) 0.0615(5) 0.0857(3) 0.0834(15) Uani 1 1 d . . . . .
H30A H 0.1221 0.0688 0.0400 0.125 Uiso 1 1 calc R U . . .
H30B H 0.0891 0.0320 0.1177 0.125 Uiso 1 1 calc R U . . .
H30C H 0.2082 -0.0014 0.0769 0.125 Uiso 1 1 calc R U . . .
C31 C 0.4460(6) 0.5289(5) 0.1125(3) 0.0706(12) Uani 1 1 d . . . . .
H31A H 0.3985 0.4728 0.0653 0.085 Uiso 1 1 calc R U . . .
H31B H 0.5418 0.5988 0.1054 0.085 Uiso 1 1 calc R U . . .
C32 C 0.3444(7) 0.5896(5) 0.1428(3) 0.0819(15) Uani 1 1 d . . . . .
H32A H 0.3986 0.6596 0.1846 0.098 Uiso 1 1 calc R U . . .
H32B H 0.3100 0.6269 0.1056 0.098 Uiso 1 1 calc R U . . .
C33 C 0.1121(8) 0.5270(7) 0.1961(4) 0.107(2) Uani 1 1 d . . . . .
H33A H 0.1648 0.6164 0.2225 0.161 Uiso 1 1 calc R U . . .
H33B H 0.0602 0.4692 0.2290 0.161 Uiso 1 1 calc R U . . .
H33C H 0.0399 0.5235 0.1578 0.161 Uiso 1 1 calc R U . . .
O1W O 0.2447(8) 0.9059(10) 0.4745(4) 0.197(3) Uani 1 1 d . U . . .
Cl3 Cl 0.09607(16) 0.29844(14) 0.92122(8) 0.0821(4) Uani 1 1 d D . . . .
O31 O 0.1569(10) 0.2105(9) 0.9158(7) 0.281(6) Uani 1 1 d D U . . .
O32 O -0.0460(9) 0.2510(7) 0.9353(6) 0.243(5) Uani 1 1 d D . . . .
O33 O 0.1882(9) 0.4121(9) 0.9628(5) 0.267(6) Uani 1 1 d D . . . .
O34 O 0.0970(10) 0.3250(11) 0.8531(4) 0.224(4) Uani 1 1 d D . . . .
Cl4 Cl 0.49631(18) 0.22447(17) 0.61005(9) 0.0887(4) Uani 1 1 d D . . . .
O41 O 0.3629(8) 0.2375(10) 0.6041(5) 0.199(3) Uani 1 1 d D . . . .
O42 O 0.4728(14) 0.0908(10) 0.6015(10) 0.152(5) Uani 0.5 1 d D . P . .
O43 O 0.575(3) 0.252(3) 0.6774(10) 0.248(11) Uani 0.5 1 d D U P . .
O44 O 0.604(2) 0.275(2) 0.5689(14) 0.202(12) Uani 0.5 1 d D . P . .
O42A O 0.481(2) 0.1825(16) 0.6762(8) 0.173(7) Uani 0.5 1 d D . P . .
O43A O 0.6055(15) 0.3606(15) 0.6382(10) 0.170(6) Uani 0.5 1 d . . P . .
O44A O 0.507(4) 0.190(3) 0.5423(10) 0.236(12) Uani 0.5 1 d . . P . .


_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
Cu1 O2 1.905(2) . ?
Cu1 N1 1.975(3) . ?
Cu1 O1 2.004(2) . ?
Cu1 O4 2.052(2) . ?
Cu1 O3 2.124(3) . ?
Cu1 Cu2 2.9604(6) . ?
Cu2 O1 1.920(2) . ?
Cu2 N2 1.972(3) . ?
Cu2 O2 1.983(3) . ?
Cu2 O6 2.010(3) . ?
Cu2 O5 2.169(3) . ?
Cl1 C4 1.741(4) . ?
Cl2 C24 1.747(4) . ?
N1 C11 1.487(4) . ?
N1 C8 1.488(5) . ?
N1 C7 1.503(4) . ?
N2 C28 1.483(5) . ?
N2 C27 1.488(5) . ?
N2 C31 1.497(5) . ?
O1 C1 1.357(4) . ?
O2 C21 1.361(4) . ?
O3 C10 1.422(5) . ?
O3 C9 1.426(5) . ?
O4 C13 1.429(5) . ?
O4 C12 1.430(4) . ?
O5 C29 1.424(5) . ?
O5 C30 1.434(6) . ?
O6 C32 1.422(6) . ?
O6 C33 1.441(6) . ?
C1 C2 1.390(5) . ?
C1 C6 1.401(5) . ?
C2 C3 1.378(6) . ?
C2 H2 0.9300 . ?
C3 C4 1.379(6) . ?
C3 H3 0.9300 . ?
C4 C5 1.381(5) . ?
C5 C6 1.394(5) . ?
C5 H5 0.9300 . ?
C6 C7 1.495(5) . ?
C7 H7A 0.9700 . ?
C7 H7B 0.9700 . ?
C8 C9 1.489(6) . ?
C8 H8A 0.9700 . ?
C8 H8B 0.9700 . ?
C9 H9A 0.9700 . ?
C9 H9B 0.9700 . ?
C10 H10A 0.9600 . ?
C10 H10B 0.9600 . ?
C10 H10C 0.9600 . ?
C11 C12 1.514(5) . ?
C11 H11A 0.9700 . ?
C11 H11B 0.9700 . ?
C12 H12A 0.9700 . ?
C12 H12B 0.9700 . ?
C13 H13A 0.9600 . ?
C13 H13B 0.9600 . ?
C13 H13C 0.9600 . ?
C21 C22 1.384(5) . ?
C21 C26 1.406(5) . ?
C22 C23 1.382(6) . ?
C22 H22 0.9300 . ?
C23 C24 1.377(6) . ?
C23 H23 0.9300 . ?
C24 C25 1.364(6) . ?
C25 C26 1.393(5) . ?
C25 H25 0.9300 . ?
C26 C27 1.497(6) . ?
C27 H27A 0.9700 . ?
C27 H27B 0.9700 . ?
C28 C29 1.501(7) . ?
C28 H28A 0.9700 . ?
C28 H28B 0.9700 . ?
C29 H29A 0.9700 . ?
C29 H29B 0.9700 . ?
C30 H30A 0.9600 . ?
C30 H30B 0.9600 . ?
C30 H30C 0.9600 . ?
C31 C32 1.517(8) . ?
C31 H31A 0.9700 . ?
C31 H31B 0.9700 . ?
C32 H32A 0.9700 . ?
C32 H32B 0.9700 . ?
C33 H33A 0.9600 . ?
C33 H33B 0.9600 . ?
C33 H33C 0.9600 . ?
Cl3 O33 1.317(7) . ?
Cl3 O32 1.320(6) . ?
Cl3 O34 1.339(7) . ?
Cl3 O31 1.351(7) . ?
Cl4 O44A 1.286(17) . ?
Cl4 O44 1.310(11) . ?
Cl4 O43 1.359(14) . ?
Cl4 O42A 1.369(10) . ?
Cl4 O41 1.375(6) . ?
Cl4 O42 1.410(10) . ?
Cl4 O43A 1.454(14) . ?
O42 O42A 1.59(2) . ?
O42 O44A 1.62(2) . ?
O43 O42A 0.92(3) . ?
O43 O43A 1.45(3) . ?
O44 O44A 1.06(3) . ?
O44 O43A 1.49(2) . ?

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
O2 Cu1 N1 175.87(11) . . ?
O2 Cu1 O1 80.11(10) . . ?
N1 Cu1 O1 95.77(11) . . ?
O2 Cu1 O4 98.38(11) . . ?
N1 Cu1 O4 84.21(11) . . ?
O1 Cu1 O4 126.18(12) . . ?
O2 Cu1 O3 99.52(12) . . ?
N1 Cu1 O3 81.73(11) . . ?
O1 Cu1 O3 111.71(13) . . ?
O4 Cu1 O3 121.41(12) . . ?
O2 Cu1 Cu2 41.41(8) . . ?
N1 Cu1 Cu2 134.50(8) . . ?
O1 Cu1 Cu2 39.95(7) . . ?
O4 Cu1 Cu2 126.16(8) . . ?
O3 Cu1 Cu2 102.90(9) . . ?
O1 Cu2 N2 175.04(12) . . ?
O1 Cu2 O2 80.28(10) . . ?
N2 Cu2 O2 94.82(12) . . ?
O1 Cu2 O6 97.90(12) . . ?
N2 Cu2 O6 85.13(13) . . ?
O2 Cu2 O6 136.70(14) . . ?
O1 Cu2 O5 100.11(12) . . ?
N2 Cu2 O5 81.48(12) . . ?
O2 Cu2 O5 101.00(13) . . ?
O6 Cu2 O5 121.65(14) . . ?
O1 Cu2 Cu1 42.09(7) . . ?
N2 Cu2 Cu1 133.24(9) . . ?
O2 Cu2 Cu1 39.44(7) . . ?
O6 Cu2 Cu1 131.63(9) . . ?
O5 Cu2 Cu1 96.07(9) . . ?
C11 N1 C8 110.0(3) . . ?
C11 N1 C7 110.3(3) . . ?
C8 N1 C7 111.7(3) . . ?
C11 N1 Cu1 106.3(2) . . ?
C8 N1 Cu1 109.7(2) . . ?
C7 N1 Cu1 108.8(2) . . ?
C28 N2 C27 111.1(3) . . ?
C28 N2 C31 111.0(3) . . ?
C27 N2 C31 110.5(3) . . ?
C28 N2 Cu2 109.9(2) . . ?
C27 N2 Cu2 108.3(2) . . ?
C31 N2 Cu2 105.8(3) . . ?
C1 O1 Cu2 129.4(2) . . ?
C1 O1 Cu1 124.3(2) . . ?
Cu2 O1 Cu1 97.96(11) . . ?
C21 O2 Cu1 132.0(2) . . ?
C21 O2 Cu2 127.4(2) . . ?
Cu1 O2 Cu2 99.14(11) . . ?
C10 O3 C9 114.7(3) . . ?
C10 O3 Cu1 131.0(3) . . ?
C9 O3 Cu1 111.6(2) . . ?
C13 O4 C12 112.1(3) . . ?
C13 O4 Cu1 127.7(3) . . ?
C12 O4 Cu1 111.7(2) . . ?
C29 O5 C30 114.0(4) . . ?
C29 O5 Cu2 110.5(2) . . ?
C30 O5 Cu2 130.9(3) . . ?
C32 O6 C33 113.6(4) . . ?
C32 O6 Cu2 112.2(3) . . ?
C33 O6 Cu2 124.7(3) . . ?
O1 C1 C2 121.6(3) . . ?
O1 C1 C6 119.0(3) . . ?
C2 C1 C6 119.3(3) . . ?
C3 C2 C1 120.9(4) . . ?
C3 C2 H2 119.6 . . ?
C1 C2 H2 119.6 . . ?
C2 C3 C4 119.7(4) . . ?
C2 C3 H3 120.2 . . ?
C4 C3 H3 120.2 . . ?
C3 C4 C5 120.5(4) . . ?
C3 C4 Cl1 120.6(3) . . ?
C5 C4 Cl1 118.9(3) . . ?
C4 C5 C6 120.3(3) . . ?
C4 C5 H5 119.8 . . ?
C6 C5 H5 119.8 . . ?
C5 C6 C1 119.2(3) . . ?
C5 C6 C7 119.5(3) . . ?
C1 C6 C7 121.3(3) . . ?
C6 C7 N1 113.7(3) . . ?
C6 C7 H7A 108.8 . . ?
N1 C7 H7A 108.8 . . ?
C6 C7 H7B 108.8 . . ?
N1 C7 H7B 108.8 . . ?
H7A C7 H7B 107.7 . . ?
N1 C8 C9 111.4(3) . . ?
N1 C8 H8A 109.3 . . ?
C9 C8 H8A 109.3 . . ?
N1 C8 H8B 109.3 . . ?
C9 C8 H8B 109.3 . . ?
H8A C8 H8B 108.0 . . ?
O3 C9 C8 106.5(3) . . ?
O3 C9 H9A 110.4 . . ?
C8 C9 H9A 110.4 . . ?
O3 C9 H9B 110.4 . . ?
C8 C9 H9B 110.4 . . ?
H9A C9 H9B 108.6 . . ?
O3 C10 H10A 109.5 . . ?
O3 C10 H10B 109.5 . . ?
H10A C10 H10B 109.5 . . ?
O3 C10 H10C 109.5 . . ?
H10A C10 H10C 109.5 . . ?
H10B C10 H10C 109.5 . . ?
N1 C11 C12 110.8(3) . . ?
N1 C11 H11A 109.5 . . ?
C12 C11 H11A 109.5 . . ?
N1 C11 H11B 109.5 . . ?
C12 C11 H11B 109.5 . . ?
H11A C11 H11B 108.1 . . ?
O4 C12 C11 106.1(3) . . ?
O4 C12 H12A 110.5 . . ?
C11 C12 H12A 110.5 . . ?
O4 C12 H12B 110.5 . . ?
C11 C12 H12B 110.5 . . ?
H12A C12 H12B 108.7 . . ?
O4 C13 H13A 109.5 . . ?
O4 C13 H13B 109.5 . . ?
H13A C13 H13B 109.5 . . ?
O4 C13 H13C 109.5 . . ?
H13A C13 H13C 109.5 . . ?
H13B C13 H13C 109.5 . . ?
O2 C21 C22 120.6(3) . . ?
O2 C21 C26 119.0(3) . . ?
C22 C21 C26 120.4(3) . . ?
C23 C22 C21 120.6(4) . . ?
C23 C22 H22 119.7 . . ?
C21 C22 H22 119.7 . . ?
C24 C23 C22 118.9(4) . . ?
C24 C23 H23 120.6 . . ?
C22 C23 H23 120.6 . . ?
C25 C24 C23 121.2(4) . . ?
C25 C24 Cl2 119.2(4) . . ?
C23 C24 Cl2 119.6(4) . . ?
C24 C25 C26 121.3(4) . . ?
C24 C25 H25 119.4 . . ?
C26 C25 H25 119.4 . . ?
C25 C26 C21 117.6(4) . . ?
C25 C26 C27 119.5(3) . . ?
C21 C26 C27 122.9(3) . . ?
N2 C27 C26 115.1(3) . . ?
N2 C27 H27A 108.5 . . ?
C26 C27 H27A 108.5 . . ?
N2 C27 H27B 108.5 . . ?
C26 C27 H27B 108.5 . . ?
H27A C27 H27B 107.5 . . ?
N2 C28 C29 111.8(4) . . ?
N2 C28 H28A 109.3 . . ?
C29 C28 H28A 109.3 . . ?
N2 C28 H28B 109.3 . . ?
C29 C28 H28B 109.3 . . ?
H28A C28 H28B 107.9 . . ?
O5 C29 C28 106.1(3) . . ?
O5 C29 H29A 110.5 . . ?
C28 C29 H29A 110.5 . . ?
O5 C29 H29B 110.5 . . ?
C28 C29 H29B 110.5 . . ?
H29A C29 H29B 108.7 . . ?
O5 C30 H30A 109.5 . . ?
O5 C30 H30B 109.5 . . ?
H30A C30 H30B 109.5 . . ?
O5 C30 H30C 109.5 . . ?
H30A C30 H30C 109.5 . . ?
H30B C30 H30C 109.5 . . ?
N2 C31 C32 110.3(3) . . ?
N2 C31 H31A 109.6 . . ?
C32 C31 H31A 109.6 . . ?
N2 C31 H31B 109.6 . . ?
C32 C31 H31B 109.6 . . ?
H31A C31 H31B 108.1 . . ?
O6 C32 C31 106.4(4) . . ?
O6 C32 H32A 110.4 . . ?
C31 C32 H32A 110.4 . . ?
O6 C32 H32B 110.4 . . ?
C31 C32 H32B 110.4 . . ?
H32A C32 H32B 108.6 . . ?
O6 C33 H33A 109.5 . . ?
O6 C33 H33B 109.5 . . ?
H33A C33 H33B 109.5 . . ?
O6 C33 H33C 109.5 . . ?
H33A C33 H33C 109.5 . . ?
H33B C33 H33C 109.5 . . ?
O33 Cl3 O32 115.0(5) . . ?
O33 Cl3 O34 104.8(6) . . ?
O32 Cl3 O34 107.2(6) . . ?
O33 Cl3 O31 111.4(6) . . ?
O32 Cl3 O31 115.2(5) . . ?
O34 Cl3 O31 101.7(6) . . ?
O44 Cl4 O43 102.6(17) . . ?
O44 Cl4 O41 123.2(14) . . ?
O43 Cl4 O41 119.3(13) . . ?
O44 Cl4 O42 102.6(11) . . ?
O43 Cl4 O42 90.9(13) . . ?
O41 Cl4 O42 112.7(7) . . ?
O44A Cl4 O42A 143.2(14) . . ?
O44A Cl4 O41 101.2(14) . . ?
O42A Cl4 O41 96.2(9) . . ?
O44A Cl4 O43A 111.1(15) . . ?
O42A Cl4 O43A 96.6(9) . . ?
O41 Cl4 O43A 101.5(8) . . ?

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
Cu2 O1 C1 C2 -8.4(5) . . . . ?
Cu1 O1 C1 C2 -149.3(3) . . . . ?
Cu2 O1 C1 C6 171.4(2) . . . . ?
Cu1 O1 C1 C6 30.5(5) . . . . ?
O1 C1 C2 C3 176.7(4) . . . . ?
C6 C1 C2 C3 -3.1(6) . . . . ?
C1 C2 C3 C4 -0.6(7) . . . . ?
C2 C3 C4 C5 2.6(6) . . . . ?
C2 C3 C4 Cl1 -175.6(3) . . . . ?
C3 C4 C5 C6 -0.8(6) . . . . ?
Cl1 C4 C5 C6 177.4(3) . . . . ?
C4 C5 C6 C1 -3.0(6) . . . . ?
C4 C5 C6 C7 175.9(3) . . . . ?
O1 C1 C6 C5 -175.0(3) . . . . ?
C2 C1 C6 C5 4.8(5) . . . . ?
O1 C1 C6 C7 6.1(5) . . . . ?
C2 C1 C6 C7 -174.1(4) . . . . ?
C5 C6 C7 N1 120.5(3) . . . . ?
C1 C6 C7 N1 -60.6(5) . . . . ?
C11 N1 C7 C6 -178.1(3) . . . . ?
C8 N1 C7 C6 -55.5(4) . . . . ?
Cu1 N1 C7 C6 65.7(3) . . . . ?
C11 N1 C8 C9 -75.4(4) . . . . ?
C7 N1 C8 C9 161.8(3) . . . . ?
Cu1 N1 C8 C9 41.1(4) . . . . ?
C10 O3 C9 C8 -164.2(4) . . . . ?
Cu1 O3 C9 C8 32.4(4) . . . . ?
N1 C8 C9 O3 -48.1(4) . . . . ?
C8 N1 C11 C12 163.3(3) . . . . ?
C7 N1 C11 C12 -73.1(4) . . . . ?
Cu1 N1 C11 C12 44.7(3) . . . . ?
C13 O4 C12 C11 -179.2(3) . . . . ?
Cu1 O4 C12 C11 30.1(3) . . . . ?
N1 C11 C12 O4 -49.7(4) . . . . ?
Cu1 O2 C21 C22 1.8(6) . . . . ?
Cu2 O2 C21 C22 -161.3(3) . . . . ?
Cu1 O2 C21 C26 -177.6(3) . . . . ?
Cu2 O2 C21 C26 19.3(5) . . . . ?
O2 C21 C22 C23 -179.2(4) . . . . ?
C26 C21 C22 C23 0.2(6) . . . . ?
C21 C22 C23 C24 -1.6(7) . . . . ?
C22 C23 C24 C25 1.4(7) . . . . ?
C22 C23 C24 Cl2 -179.6(3) . . . . ?
C23 C24 C25 C26 0.1(7) . . . . ?
Cl2 C24 C25 C26 -178.9(3) . . . . ?
C24 C25 C26 C21 -1.4(6) . . . . ?
C24 C25 C26 C27 175.8(4) . . . . ?
O2 C21 C26 C25 -179.3(3) . . . . ?
C22 C21 C26 C25 1.3(6) . . . . ?
O2 C21 C26 C27 3.6(6) . . . . ?
C22 C21 C26 C27 -175.8(4) . . . . ?
C28 N2 C27 C26 -54.0(4) . . . . ?
C31 N2 C27 C26 -177.7(3) . . . . ?
Cu2 N2 C27 C26 66.8(4) . . . . ?
C25 C26 C27 N2 130.7(4) . . . . ?
C21 C26 C27 N2 -52.3(5) . . . . ?
C27 N2 C28 C29 161.9(3) . . . . ?
C31 N2 C28 C29 -74.6(4) . . . . ?
Cu2 N2 C28 C29 42.0(4) . . . . ?
C30 O5 C29 C28 -167.9(4) . . . . ?
Cu2 O5 C29 C28 33.4(4) . . . . ?
N2 C28 C29 O5 -49.8(5) . . . . ?
C28 N2 C31 C32 162.1(4) . . . . ?
C27 N2 C31 C32 -74.1(5) . . . . ?
Cu2 N2 C31 C32 42.9(5) . . . . ?
C33 O6 C32 C31 178.8(5) . . . . ?
Cu2 O6 C32 C31 30.6(5) . . . . ?
N2 C31 C32 O6 -48.8(6) . . . . ?

_refine_diff_density_max         1.450
_refine_diff_density_min         -0.798
_refine_diff_density_rms         0.097

_shelxl_version_number           2014/6

####################################################################### 
# 
# 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_3
_database_code_depnum_ccdc_archive 'CCDC 1038857'
_audit_update_record             
;
2016-05-05 deposited with the CCDC.
2016-05-18 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/6
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C26 H38 Cl2 Cu2 N4 O12'
_chemical_formula_sum            'C26 H38 Cl2 Cu2 N4 O12'
_chemical_formula_weight         796.58

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'

_space_group_crystal_system      orthorhombic
_space_group_IT_number           61
_space_group_name_H-M_alt        'P b c a'
_space_group_name_Hall           '-P 2ac 2ab'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;

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

_cell_length_a                   14.1999(4)
_cell_length_b                   13.2826(4)
_cell_length_c                   17.8412(5)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     3365.06(17)
_cell_formula_units_Z            4
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    2390
_cell_measurement_theta_min      2.11
_cell_measurement_theta_max      26.66

_exptl_crystal_description       block
_exptl_crystal_colour            'deep green'
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.572
_exptl_crystal_F_000             1640
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.34
_exptl_crystal_size_mid          0.18
_exptl_crystal_size_min          0.16
_exptl_absorpt_coefficient_mu    1.487
_exptl_absorpt_correction_type   MULTI-SCAN
_exptl_absorpt_correction_T_min  0.664
_exptl_absorpt_correction_T_max  0.733
_exptl_absorpt_process_details   'BRUKER SADABS'

_exptl_absorpt_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 SMART APEX CCD DIFFRACTOMETER'
_diffrn_measurement_method       'OMEGA-PHI SCAN'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            39975
_diffrn_reflns_av_unetI/netI     0.0161
_diffrn_reflns_av_R_equivalents  0.0291
_diffrn_reflns_limit_h_min       -17
_diffrn_reflns_limit_h_max       18
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_limit_l_max       23
_diffrn_reflns_theta_min         2.283
_diffrn_reflns_theta_max         27.649
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.995
_diffrn_measured_fraction_theta_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.995
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.995
_diffrn_reflns_point_group_measured_fraction_full 1.000
_reflns_number_total             3899
_reflns_number_gt                3181
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;

_computing_data_collection       'BRUKER SMART'
_computing_cell_refinement       'BRUKER SMART'
_computing_data_reduction        'BRUKER SAINT'
_computing_structure_solution    'SHELX97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-2014/6 (Sheldrick, 2014)'
_computing_molecular_graphics    'Ortep3 for Windows (Farrugia,1997)'
_computing_publication_material  'Wingx 2013.03 (Farrugia, 2012)'

_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0450P)²+1.1326P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         3899
_refine_ls_number_parameters     208
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0377
_refine_ls_R_factor_gt           0.0279
_refine_ls_wR_factor_ref         0.0823
_refine_ls_wR_factor_gt          0.0764
_refine_ls_goodness_of_fit_ref   1.030
_refine_ls_restrained_S_all      1.030
_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_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Cu Cu 0.44989(2) 0.03856(2) 0.56917(2) 0.03465(9) Uani 1 1 d . . . . .
Cl Cl 0.79553(3) -0.28480(4) 0.73970(3) 0.04967(14) Uani 1 1 d . . . . .
O3 O 0.30374(10) -0.03545(11) 0.56848(8) 0.0503(4) Uani 1 1 d . . . . .
O4 O 0.39583(9) 0.17363(10) 0.59382(8) 0.0436(3) Uani 1 1 d . . . . .
O1 O 0.54385(9) -0.05945(11) 0.53960(8) 0.0421(3) Uani 1 1 d . . . . .
O5 O 0.54196(11) 0.20571(15) 0.57279(10) 0.0684(5) Uani 1 1 d . . . . .
O2 O 0.55482(13) 0.10417(16) 0.84304(9) 0.0728(5) Uani 1 1 d . . . . .
N1 N 0.44079(10) -0.01069(12) 0.67647(9) 0.0356(3) Uani 1 1 d . . . . .
O6 O 0.44610(15) 0.32642(13) 0.59876(12) 0.0802(6) Uani 1 1 d . . . . .
N2 N 0.46309(13) 0.23791(14) 0.58793(10) 0.0463(4) Uani 1 1 d . . . . .
C4 C 0.72141(13) -0.21443(14) 0.68139(11) 0.0391(4) Uani 1 1 d . . . . .
C5 C 0.63205(12) -0.18893(13) 0.70551(11) 0.0383(4) Uani 1 1 d . . . . .
H5 H 0.6124 -0.2065 0.7535 0.046 Uiso 1 1 calc R U . . .
C8 C 0.49935(14) 0.05490(14) 0.72572(10) 0.0400(4) Uani 1 1 d . . . . .
H8A H 0.4855 0.1245 0.7134 0.048 Uiso 1 1 calc R U . . .
H8B H 0.5650 0.0432 0.7135 0.048 Uiso 1 1 calc R U . . .
C12 C 0.27512(14) -0.05782(18) 0.64307(13) 0.0531(5) Uani 1 1 d . . . . .
H12A H 0.2794 -0.1297 0.6520 0.064 Uiso 1 1 calc R U . . .
H12B H 0.2103 -0.0372 0.6506 0.064 Uiso 1 1 calc R U . . .
C6 C 0.57158(12) -0.13687(13) 0.65790(10) 0.0353(4) Uani 1 1 d . . . . .
C2 C 0.69396(14) -0.13373(16) 0.56431(11) 0.0446(5) Uani 1 1 d . . . . .
H2 H 0.7152 -0.1144 0.5171 0.054 Uiso 1 1 calc R U . . .
C3 C 0.75312(13) -0.18624(15) 0.61144(11) 0.0443(4) Uani 1 1 d . . . . .
H3 H 0.8139 -0.2025 0.5962 0.053 Uiso 1 1 calc R U . . .
C11 C 0.33896(13) -0.00178(17) 0.69669(11) 0.0453(5) Uani 1 1 d . . . . .
H11A H 0.3215 0.0688 0.6970 0.054 Uiso 1 1 calc R U . . .
H11B H 0.3297 -0.0280 0.7469 0.054 Uiso 1 1 calc R U . . .
C1 C 0.60277(12) -0.10925(14) 0.58648(10) 0.0367(4) Uani 1 1 d . . . . .
C7 C 0.47090(12) -0.11886(14) 0.68085(12) 0.0392(4) Uani 1 1 d . . . . .
H7A H 0.4301 -0.1587 0.6489 0.047 Uiso 1 1 calc R U . . .
H7B H 0.4625 -0.1423 0.7319 0.047 Uiso 1 1 calc R U . . .
C9 C 0.48756(18) 0.04199(17) 0.80960(12) 0.0550(5) Uani 1 1 d . . . . .
H9A H 0.4247 0.0616 0.8250 0.066 Uiso 1 1 calc R U . . .
H9B H 0.4977 -0.0276 0.8238 0.066 Uiso 1 1 calc R U . . .
C13 C 0.26572(19) -0.1025(2) 0.51383(16) 0.0756(8) Uani 1 1 d . . . . .
H13A H 0.2876 -0.0834 0.4649 0.113 Uiso 1 1 calc R U . . .
H13B H 0.2857 -0.1700 0.5246 0.113 Uiso 1 1 calc R U . . .
H13C H 0.1982 -0.0992 0.5151 0.113 Uiso 1 1 calc R U . . .
C10 C 0.5442(3) 0.1136(3) 0.92122(14) 0.1001(13) Uani 1 1 d . . . . .
H10A H 0.5924 0.1571 0.9406 0.150 Uiso 1 1 calc R U . . .
H10B H 0.4835 0.1417 0.9322 0.150 Uiso 1 1 calc R U . . .
H10C H 0.5495 0.0485 0.9442 0.150 Uiso 1 1 calc R U . . .


_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
Cu O1 1.9374(12) . ?
Cu O1 1.9625(14) 5_656 ?
Cu O4 2.0004(13) . ?
Cu N1 2.0271(16) . ?
Cu O3 2.2965(15) . ?
Cu Cu 3.0278(4) 5_656 ?
Cl C4 1.7502(18) . ?
O3 C12 1.423(3) . ?
O3 C13 1.426(3) . ?
O4 N2 1.285(2) . ?
O1 C1 1.355(2) . ?
O1 Cu 1.9624(14) 5_656 ?
O5 N2 1.229(2) . ?
O2 C9 1.397(3) . ?
O2 C10 1.409(3) . ?
N1 C8 1.491(2) . ?
N1 C11 1.495(2) . ?
N1 C7 1.501(2) . ?
O6 N2 1.216(3) . ?
C4 C3 1.379(3) . ?
C4 C5 1.382(3) . ?
C5 C6 1.392(3) . ?
C5 H5 0.9300 . ?
C8 C9 1.516(3) . ?
C8 H8A 0.9700 . ?
C8 H8B 0.9700 . ?
C12 C11 1.514(3) . ?
C12 H12A 0.9700 . ?
C12 H12B 0.9700 . ?
C6 C1 1.398(3) . ?
C6 C7 1.506(2) . ?
C2 C3 1.378(3) . ?
C2 C1 1.392(3) . ?
C2 H2 0.9300 . ?
C3 H3 0.9300 . ?
C11 H11A 0.9700 . ?
C11 H11B 0.9700 . ?
C7 H7A 0.9700 . ?
C7 H7B 0.9700 . ?
C9 H9A 0.9700 . ?
C9 H9B 0.9700 . ?
C13 H13A 0.9600 . ?
C13 H13B 0.9600 . ?
C13 H13C 0.9600 . ?
C10 H10A 0.9600 . ?
C10 H10B 0.9600 . ?
C10 H10C 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
O1 Cu O1 78.14(6) . 5_656 ?
O1 Cu O4 157.95(6) . . ?
O1 Cu O4 96.20(6) 5_656 . ?
O1 Cu N1 94.83(6) . . ?
O1 Cu N1 169.23(6) 5_656 . ?
O4 Cu N1 93.29(6) . . ?
O1 Cu O3 109.46(6) . . ?
O1 Cu O3 95.51(5) 5_656 . ?
O4 Cu O3 92.20(5) . . ?
N1 Cu O3 79.01(5) . . ?
O1 Cu Cu 39.37(4) . 5_656 ?
O1 Cu Cu 38.77(4) 5_656 5_656 ?
O4 Cu Cu 131.54(4) . 5_656 ?
N1 Cu Cu 133.68(4) . 5_656 ?
O3 Cu Cu 105.99(4) . 5_656 ?
C12 O3 C13 113.63(18) . . ?
C12 O3 Cu 110.02(12) . . ?
C13 O3 Cu 127.81(14) . . ?
N2 O4 Cu 107.01(11) . . ?
C1 O1 Cu 125.80(11) . . ?
C1 O1 Cu 130.64(11) . 5_656 ?
Cu O1 Cu 101.86(6) . 5_656 ?
C9 O2 C10 113.7(2) . . ?
C8 N1 C11 110.55(15) . . ?
C8 N1 C7 111.70(14) . . ?
C11 N1 C7 109.80(15) . . ?
C8 N1 Cu 109.41(11) . . ?
C11 N1 Cu 105.31(11) . . ?
C7 N1 Cu 109.87(11) . . ?
O6 N2 O5 123.5(2) . . ?
O6 N2 O4 118.80(19) . . ?
O5 N2 O4 117.65(18) . . ?
C3 C4 C5 121.01(17) . . ?
C3 C4 Cl 119.12(14) . . ?
C5 C4 Cl 119.86(15) . . ?
C4 C5 C6 119.88(17) . . ?
C4 C5 H5 120.1 . . ?
C6 C5 H5 120.1 . . ?
N1 C8 C9 117.02(16) . . ?
N1 C8 H8A 108.0 . . ?
C9 C8 H8A 108.0 . . ?
N1 C8 H8B 108.0 . . ?
C9 C8 H8B 108.0 . . ?
H8A C8 H8B 107.3 . . ?
O3 C12 C11 108.51(16) . . ?
O3 C12 H12A 110.0 . . ?
C11 C12 H12A 110.0 . . ?
O3 C12 H12B 110.0 . . ?
C11 C12 H12B 110.0 . . ?
H12A C12 H12B 108.4 . . ?
C5 C6 C1 119.42(16) . . ?
C5 C6 C7 119.90(17) . . ?
C1 C6 C7 120.45(17) . . ?
C3 C2 C1 120.79(18) . . ?
C3 C2 H2 119.6 . . ?
C1 C2 H2 119.6 . . ?
C2 C3 C4 119.39(17) . . ?
C2 C3 H3 120.3 . . ?
C4 C3 H3 120.3 . . ?
N1 C11 C12 112.82(16) . . ?
N1 C11 H11A 109.0 . . ?
C12 C11 H11A 109.0 . . ?
N1 C11 H11B 109.0 . . ?
C12 C11 H11B 109.0 . . ?
H11A C11 H11B 107.8 . . ?
O1 C1 C2 120.85(17) . . ?
O1 C1 C6 119.66(15) . . ?
C2 C1 C6 119.48(17) . . ?
N1 C7 C6 114.10(15) . . ?
N1 C7 H7A 108.7 . . ?
C6 C7 H7A 108.7 . . ?
N1 C7 H7B 108.7 . . ?
C6 C7 H7B 108.7 . . ?
H7A C7 H7B 107.6 . . ?
O2 C9 C8 106.22(18) . . ?
O2 C9 H9A 110.5 . . ?
C8 C9 H9A 110.5 . . ?
O2 C9 H9B 110.5 . . ?
C8 C9 H9B 110.5 . . ?
H9A C9 H9B 108.7 . . ?
O3 C13 H13A 109.5 . . ?
O3 C13 H13B 109.5 . . ?
H13A C13 H13B 109.5 . . ?
O3 C13 H13C 109.5 . . ?
H13A C13 H13C 109.5 . . ?
H13B C13 H13C 109.5 . . ?
O2 C10 H10A 109.5 . . ?
O2 C10 H10B 109.5 . . ?
H10A C10 H10B 109.5 . . ?
O2 C10 H10C 109.5 . . ?
H10A C10 H10C 109.5 . . ?
H10B C10 H10C 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
Cu O4 N2 O6 178.31(17) . . . . ?
Cu O4 N2 O5 -2.9(2) . . . . ?
C3 C4 C5 C6 2.1(3) . . . . ?
Cl C4 C5 C6 -177.13(14) . . . . ?
C11 N1 C8 C9 53.6(2) . . . . ?
C7 N1 C8 C9 -69.0(2) . . . . ?
Cu N1 C8 C9 169.09(15) . . . . ?
C13 O3 C12 C11 164.81(19) . . . . ?
Cu O3 C12 C11 14.16(19) . . . . ?
C4 C5 C6 C1 -1.2(3) . . . . ?
C4 C5 C6 C7 173.40(17) . . . . ?
C1 C2 C3 C4 -0.2(3) . . . . ?
C5 C4 C3 C2 -1.4(3) . . . . ?
Cl C4 C3 C2 177.84(16) . . . . ?
C8 N1 C11 C12 173.67(16) . . . . ?
C7 N1 C11 C12 -62.6(2) . . . . ?
Cu N1 C11 C12 55.60(19) . . . . ?
O3 C12 C11 N1 -45.9(2) . . . . ?
Cu O1 C1 C2 -145.63(15) . . . . ?
Cu O1 C1 C2 16.7(3) 5_656 . . . ?
Cu O1 C1 C6 34.7(2) . . . . ?
Cu O1 C1 C6 -162.97(13) 5_656 . . . ?
C3 C2 C1 O1 -178.62(18) . . . . ?
C3 C2 C1 C6 1.1(3) . . . . ?
C5 C6 C1 O1 179.33(16) . . . . ?
C7 C6 C1 O1 4.7(3) . . . . ?
C5 C6 C1 C2 -0.4(3) . . . . ?
C7 C6 C1 C2 -174.95(18) . . . . ?
C8 N1 C7 C6 -59.7(2) . . . . ?
C11 N1 C7 C6 177.24(16) . . . . ?
Cu N1 C7 C6 61.87(18) . . . . ?
C5 C6 C7 N1 127.30(18) . . . . ?
C1 C6 C7 N1 -58.1(2) . . . . ?
C10 O2 C9 C8 170.6(3) . . . . ?
N1 C8 C9 O2 174.86(17) . . . . ?

_refine_diff_density_max         0.412
_refine_diff_density_min         -0.247
_refine_diff_density_rms         0.052

_shelxl_version_number           2014/6

####################################################################### 
# 
# 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_4
_database_code_depnum_ccdc_archive 'CCDC 1038858'
_audit_update_record             
;
2016-05-05 deposited with the CCDC.
2016-05-18 downloaded from the CCDC.
;

_vrf_PLAT430_I                   
;
PROBLEM: Short Inter D...A Contact  O1W    ..  O1W     ..       1.39 Ang.  
RESPONSE: O1w is an oxygen of water molecule at half occupancy (no H atoms)
;
# end Validation Reply Form

_audit_creation_method           SHELXL-2014/6
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C30 H42 Cl2 Cu2 N2 O10, H2 O'
_chemical_formula_sum            'C30 H46 Cl2 Cu2 N2 O11'
_chemical_formula_weight         808.67

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'

_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;

loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   8.9325(19)
_cell_length_b                   9.701(2)
_cell_length_c                   11.314(2)
_cell_angle_alpha                79.587(6)
_cell_angle_beta                 71.215(6)
_cell_angle_gamma                80.545(6)
_cell_volume                     906.9(3)
_cell_formula_units_Z            1
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    3146
_cell_measurement_theta_min      2.72
_cell_measurement_theta_max      24.91

_exptl_crystal_description       needle
_exptl_crystal_colour            'deep green'
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.481
_exptl_crystal_F_000             420
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.34
_exptl_crystal_size_mid          0.18
_exptl_crystal_size_min          0.16
_exptl_absorpt_coefficient_mu    1.377
_exptl_absorpt_correction_type   MULTI-SCAN
_exptl_absorpt_correction_T_min  0.650
_exptl_absorpt_correction_T_max  0.790
_exptl_absorpt_process_details   'BRUKER SADABS'

_exptl_absorpt_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  'BRUKER SMART APEX CCD DIFFRACTOMETER'
_diffrn_measurement_method       'OMEGA-PHI SCAN'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            10177
_diffrn_reflns_av_unetI/netI     0.0408
_diffrn_reflns_av_R_equivalents  0.0392
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_theta_min         1.919
_diffrn_reflns_theta_max         25.350
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.981
_diffrn_measured_fraction_theta_full 0.984
_diffrn_reflns_Laue_measured_fraction_max 0.981
_diffrn_reflns_Laue_measured_fraction_full 0.984
_diffrn_reflns_point_group_measured_fraction_max 0.981
_diffrn_reflns_point_group_measured_fraction_full 0.984
_reflns_number_total             3258
_reflns_number_gt                2711
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;

_computing_data_collection       'BRUKER SMART'
_computing_cell_refinement       'BRUKER SMART'
_computing_data_reduction        'BRUKER SAINT'
_computing_structure_solution    'SHELX97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-2014/6 (Sheldrick, 2014)'
_computing_molecular_graphics    'Ortep3 for Windows (Farrugia,1997)'
_computing_publication_material  'Wingx 2013.03 (Farrugia, 2012)'

_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.1626P)²+0.5068P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         3258
_refine_ls_number_parameters     220
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0859
_refine_ls_R_factor_gt           0.0724
_refine_ls_wR_factor_ref         0.2221
_refine_ls_wR_factor_gt          0.2003
_refine_ls_goodness_of_fit_ref   1.096
_refine_ls_restrained_S_all      1.096
_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_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Cu Cu 0.47242(7) 0.12471(5) 0.07289(5) 0.0348(3) Uani 1 1 d . . . . .
Cl1 Cl 0.8929(2) -0.36307(17) 0.43591(15) 0.0626(5) Uani 1 1 d . . . . .
N1 N 0.5928(5) 0.1829(4) 0.1791(4) 0.0375(9) Uani 1 1 d . . . . .
O1 O 0.5984(4) -0.0586(3) 0.0532(3) 0.0376(8) Uani 1 1 d . . . . .
O2 O 0.6016(8) 0.3127(6) 0.4075(4) 0.0873(17) Uani 1 1 d . . . . .
O3 O 0.6368(5) 0.2912(4) -0.0696(3) 0.0516(10) Uani 1 1 d . . . . .
O4 O 0.2991(4) 0.2703(4) 0.1178(3) 0.0420(8) Uani 1 1 d . . . . .
O5 O 0.1683(7) 0.0991(5) 0.2445(6) 0.0877(17) Uani 1 1 d . . . . .
C1 C 0.6723(6) -0.1317(5) 0.1371(5) 0.0361(11) Uani 1 1 d . . . . .
C2 C 0.6761(7) -0.2761(5) 0.1670(5) 0.0434(12) Uani 1 1 d . . . . .
H2 H 0.6324 -0.3257 0.1256 0.052 Uiso 1 1 calc R U . . .
C3 C 0.7445(7) -0.3491(5) 0.2583(5) 0.0451(12) Uani 1 1 d . . . . .
H3 H 0.7447 -0.4464 0.2791 0.054 Uiso 1 1 calc R U . . .
C4 C 0.8119(6) -0.2747(6) 0.3174(5) 0.0435(12) Uani 1 1 d . . . . .
C5 C 0.8141(6) -0.1324(6) 0.2869(5) 0.0430(12) Uani 1 1 d . . . . .
H5 H 0.8625 -0.0845 0.3262 0.052 Uiso 1 1 calc R U . . .
C6 C 0.7436(6) -0.0582(5) 0.1966(5) 0.0378(11) Uani 1 1 d . . . . .
C7 C 0.7519(7) 0.0965(5) 0.1575(5) 0.0425(12) Uani 1 1 d . . . . .
H7A H 0.8105 0.1126 0.0686 0.051 Uiso 1 1 calc R U . . .
H7B H 0.8111 0.1286 0.2037 0.051 Uiso 1 1 calc R U . . .
C8 C 0.4935(7) 0.1627(6) 0.3148(5) 0.0458(13) Uani 1 1 d . . . . .
H8A H 0.4607 0.0686 0.3337 0.055 Uiso 1 1 calc R U . . .
H8B H 0.3978 0.2288 0.3236 0.055 Uiso 1 1 calc R U . . .
C9 C 0.5662(10) 0.1797(8) 0.4151(6) 0.0673(19) Uani 1 1 d . . . . .
H9A H 0.4924 0.1542 0.4975 0.081 Uiso 1 1 calc R U . . .
H9B H 0.6628 0.1148 0.4072 0.081 Uiso 1 1 calc R U . . .
C10 C 0.6518(13) 0.3260(12) 0.5122(7) 0.105(3) Uani 1 1 d . . . . .
H10A H 0.5617 0.3260 0.5868 0.158 Uiso 1 1 calc R U . . .
H10B H 0.6977 0.4128 0.4963 0.158 Uiso 1 1 calc R U . . .
H10C H 0.7296 0.2482 0.5240 0.158 Uiso 1 1 calc R U . . .
C11 C 0.6155(7) 0.3348(5) 0.1347(5) 0.0428(12) Uani 1 1 d . . . . .
H11A H 0.6738 0.3650 0.1827 0.051 Uiso 1 1 calc R U . . .
H11B H 0.5121 0.3904 0.1513 0.051 Uiso 1 1 calc R U . . .
C12 C 0.7032(7) 0.3632(6) -0.0024(5) 0.0475(13) Uani 1 1 d . . . . .
H12A H 0.6930 0.4638 -0.0311 0.057 Uiso 1 1 calc R U . . .
H12B H 0.8153 0.3300 -0.0171 0.057 Uiso 1 1 calc R U . . .
C13 C 0.7355(10) 0.2758(10) -0.1947(6) 0.080(2) Uani 1 1 d . . . . .
H13A H 0.7467 0.3671 -0.2440 0.119 Uiso 1 1 calc R U . . .
H13B H 0.6879 0.2201 -0.2318 0.119 Uiso 1 1 calc R U . . .
H13C H 0.8384 0.2297 -0.1924 0.119 Uiso 1 1 calc R U . . .
C14 C 0.1727(7) 0.2231(6) 0.1964(6) 0.0534(14) Uani 1 1 d . . . . .
C15 C 0.0311(9) 0.3303(9) 0.2296(9) 0.089(3) Uani 1 1 d . . . . .
H15A H -0.0631 0.2835 0.2674 0.133 Uiso 1 1 calc R U . . .
H15B H 0.0224 0.3914 0.1548 0.133 Uiso 1 1 calc R U . . .
H15C H 0.0431 0.3849 0.2882 0.133 Uiso 1 1 calc R U . . .
O1W O 0.925(2) 0.022(2) 0.4927(18) 0.152(7) Uani 0.5 1 d . . P . .


_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
Cu O4 1.919(3) . ?
Cu O1 1.950(3) . ?
Cu O1 1.972(3) 2_655 ?
Cu N1 2.048(4) . ?
Cu O3 2.383(4) . ?
Cu Cu 3.0569(11) 2_655 ?
Cl1 C4 1.750(5) . ?
N1 C11 1.493(6) . ?
N1 C7 1.498(7) . ?
N1 C8 1.501(6) . ?
O1 C1 1.359(5) . ?
O1 Cu 1.972(3) 2_655 ?
O2 C9 1.360(8) . ?
O2 C10 1.427(9) . ?
O3 C13 1.425(7) . ?
O3 C12 1.426(7) . ?
O4 C14 1.285(7) . ?
O5 C14 1.228(8) . ?
C1 C2 1.378(7) . ?
C1 C6 1.402(7) . ?
C2 C3 1.393(7) . ?
C2 H2 0.9300 . ?
C3 C4 1.381(8) . ?
C3 H3 0.9300 . ?
C4 C5 1.363(7) . ?
C5 C6 1.399(7) . ?
C5 H5 0.9300 . ?
C6 C7 1.493(7) . ?
C7 H7A 0.9700 . ?
C7 H7B 0.9700 . ?
C8 C9 1.520(9) . ?
C8 H8A 0.9700 . ?
C8 H8B 0.9700 . ?
C9 H9A 0.9700 . ?
C9 H9B 0.9700 . ?
C10 H10A 0.9600 . ?
C10 H10B 0.9600 . ?
C10 H10C 0.9600 . ?
C11 C12 1.494(8) . ?
C11 H11A 0.9700 . ?
C11 H11B 0.9700 . ?
C12 H12A 0.9700 . ?
C12 H12B 0.9700 . ?
C13 H13A 0.9600 . ?
C13 H13B 0.9600 . ?
C13 H13C 0.9600 . ?
C14 C15 1.491(9) . ?
C15 H15A 0.9600 . ?
C15 H15B 0.9600 . ?
C15 H15C 0.9600 . ?
O1W O1W 1.40(3) 2_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
O4 Cu O1 162.95(16) . . ?
O4 Cu O1 96.82(15) . 2_655 ?
O1 Cu O1 77.60(14) . 2_655 ?
O4 Cu N1 93.15(16) . . ?
O1 Cu N1 94.64(15) . . ?
O1 Cu N1 167.96(16) 2_655 . ?
O4 Cu O3 91.27(15) . . ?
O1 Cu O3 105.32(15) . . ?
O1 Cu O3 96.89(14) 2_655 . ?
N1 Cu O3 76.11(15) . . ?
O4 Cu Cu 133.35(11) . 2_655 ?
O1 Cu Cu 39.06(9) . 2_655 ?
O1 Cu Cu 38.54(9) 2_655 2_655 ?
N1 Cu Cu 133.05(12) . 2_655 ?
O3 Cu Cu 104.23(10) . 2_655 ?
C11 N1 C7 109.4(4) . . ?
C11 N1 C8 110.7(4) . . ?
C7 N1 C8 112.1(4) . . ?
C11 N1 Cu 107.1(3) . . ?
C7 N1 Cu 109.1(3) . . ?
C8 N1 Cu 108.3(3) . . ?
C1 O1 Cu 124.2(3) . . ?
C1 O1 Cu 130.4(3) . 2_655 ?
Cu O1 Cu 102.40(14) . 2_655 ?
C9 O2 C10 110.9(6) . . ?
C13 O3 C12 113.9(5) . . ?
C13 O3 Cu 126.8(4) . . ?
C12 O3 Cu 110.1(3) . . ?
C14 O4 Cu 113.0(4) . . ?
O1 C1 C2 121.6(5) . . ?
O1 C1 C6 119.2(4) . . ?
C2 C1 C6 119.2(4) . . ?
C1 C2 C3 121.1(5) . . ?
C1 C2 H2 119.4 . . ?
C3 C2 H2 119.4 . . ?
C4 C3 C2 118.9(5) . . ?
C4 C3 H3 120.6 . . ?
C2 C3 H3 120.6 . . ?
C5 C4 C3 121.2(5) . . ?
C5 C4 Cl1 119.0(4) . . ?
C3 C4 Cl1 119.8(4) . . ?
C4 C5 C6 120.1(5) . . ?
C4 C5 H5 119.9 . . ?
C6 C5 H5 119.9 . . ?
C5 C6 C1 119.4(5) . . ?
C5 C6 C7 120.8(5) . . ?
C1 C6 C7 119.7(4) . . ?
C6 C7 N1 114.1(4) . . ?
C6 C7 H7A 108.7 . . ?
N1 C7 H7A 108.7 . . ?
C6 C7 H7B 108.7 . . ?
N1 C7 H7B 108.7 . . ?
H7A C7 H7B 107.6 . . ?
N1 C8 C9 118.6(5) . . ?
N1 C8 H8A 107.7 . . ?
C9 C8 H8A 107.7 . . ?
N1 C8 H8B 107.7 . . ?
C9 C8 H8B 107.7 . . ?
H8A C8 H8B 107.1 . . ?
O2 C9 C8 113.6(6) . . ?
O2 C9 H9A 108.8 . . ?
C8 C9 H9A 108.8 . . ?
O2 C9 H9B 108.8 . . ?
C8 C9 H9B 108.8 . . ?
H9A C9 H9B 107.7 . . ?
O2 C10 H10A 109.5 . . ?
O2 C10 H10B 109.5 . . ?
H10A C10 H10B 109.5 . . ?
O2 C10 H10C 109.5 . . ?
H10A C10 H10C 109.5 . . ?
H10B C10 H10C 109.5 . . ?
N1 C11 C12 113.2(4) . . ?
N1 C11 H11A 108.9 . . ?
C12 C11 H11A 108.9 . . ?
N1 C11 H11B 108.9 . . ?
C12 C11 H11B 108.9 . . ?
H11A C11 H11B 107.8 . . ?
O3 C12 C11 108.3(4) . . ?
O3 C12 H12A 110.0 . . ?
C11 C12 H12A 110.0 . . ?
O3 C12 H12B 110.0 . . ?
C11 C12 H12B 110.0 . . ?
H12A C12 H12B 108.4 . . ?
O3 C13 H13A 109.5 . . ?
O3 C13 H13B 109.5 . . ?
H13A C13 H13B 109.5 . . ?
O3 C13 H13C 109.5 . . ?
H13A C13 H13C 109.5 . . ?
H13B C13 H13C 109.5 . . ?
O5 C14 O4 122.9(6) . . ?
O5 C14 C15 121.6(6) . . ?
O4 C14 C15 115.5(6) . . ?
C14 C15 H15A 109.5 . . ?
C14 C15 H15B 109.5 . . ?
H15A C15 H15B 109.5 . . ?
C14 C15 H15C 109.5 . . ?
H15A C15 H15C 109.5 . . ?
H15B C15 H15C 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
Cu O1 C1 C2 140.6(4) . . . . ?
Cu O1 C1 C2 -16.1(7) 2_655 . . . ?
Cu O1 C1 C6 -38.1(6) . . . . ?
Cu O1 C1 C6 165.2(3) 2_655 . . . ?
O1 C1 C2 C3 -176.4(5) . . . . ?
C6 C1 C2 C3 2.3(8) . . . . ?
C1 C2 C3 C4 -1.3(8) . . . . ?
C2 C3 C4 C5 -0.7(8) . . . . ?
C2 C3 C4 Cl1 178.0(4) . . . . ?
C3 C4 C5 C6 1.7(8) . . . . ?
Cl1 C4 C5 C6 -177.1(4) . . . . ?
C4 C5 C6 C1 -0.6(8) . . . . ?
C4 C5 C6 C7 -177.0(5) . . . . ?
O1 C1 C6 C5 177.4(4) . . . . ?
C2 C1 C6 C5 -1.4(8) . . . . ?
O1 C1 C6 C7 -6.2(7) . . . . ?
C2 C1 C6 C7 175.0(5) . . . . ?
C5 C6 C7 N1 -121.2(5) . . . . ?
C1 C6 C7 N1 62.4(6) . . . . ?
C11 N1 C7 C6 -179.0(4) . . . . ?
C8 N1 C7 C6 57.9(5) . . . . ?
Cu N1 C7 C6 -62.1(4) . . . . ?
C11 N1 C8 C9 -71.0(6) . . . . ?
C7 N1 C8 C9 51.5(6) . . . . ?
Cu N1 C8 C9 171.9(4) . . . . ?
C10 O2 C9 C8 173.2(6) . . . . ?
N1 C8 C9 O2 64.3(8) . . . . ?
C7 N1 C11 C12 60.3(5) . . . . ?
C8 N1 C11 C12 -175.7(5) . . . . ?
Cu N1 C11 C12 -57.8(5) . . . . ?
C13 O3 C12 C11 -163.2(6) . . . . ?
Cu O3 C12 C11 -13.8(5) . . . . ?
N1 C11 C12 O3 46.0(6) . . . . ?
Cu O4 C14 O5 5.1(8) . . . . ?
Cu O4 C14 C15 -176.9(5) . . . . ?

_refine_diff_density_max         2.024
_refine_diff_density_min         -1.225
_refine_diff_density_rms         0.213

_shelxl_version_number           2014/6

