# Electronic Supplementary Material (ESI) for Dalton Transactions.
# 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_lm-1
_database_code_depnum_ccdc_archive 'CCDC 1050967'
_audit_update_record             
;
2015-05-21 deposited with the CCDC.
2015-06-26 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C23 H18 Cu2 N2 O15'
_chemical_formula_sum            'C23 H18 Cu2 N2 O15'
_chemical_formula_weight         689.47

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'
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'
O O 0.0106 0.0060 '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'
_space_group_name_Hall           '-P 1'

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

_cell_length_a                   6.9343(5)
_cell_length_b                   10.9163(9)
_cell_length_c                   16.8658(13)
_cell_angle_alpha                95.7880(10)
_cell_angle_beta                 94.3610(10)
_cell_angle_gamma                96.8550(10)
_cell_volume                     1256.08(17)
_cell_formula_units_Z            2
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    ?
_cell_measurement_theta_min      2.13
_cell_measurement_theta_max      26.00

_exptl_crystal_description       BLOCK
_exptl_crystal_colour            BLUE
_exptl_crystal_size_max          0.15
_exptl_crystal_size_mid          0.13
_exptl_crystal_size_min          0.11
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.823
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             696
_exptl_absorpt_coefficient_mu    1.777
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.766
_exptl_absorpt_correction_T_max  0.822
_exptl_absorpt_process_details   SADABS

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      296(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            6908
_diffrn_reflns_av_R_equivalents  0.0130
_diffrn_reflns_av_sigmaI/netI    0.0260
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_theta_min         2.13
_diffrn_reflns_theta_max         26.00
_reflns_number_total             4866
_reflns_number_gt                4275
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'SMART (Bruker, 2001)'
_computing_cell_refinement       'SMART (Bruker, 2001)'
_computing_data_reduction        'SAINT+ (Bruker, 1999)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_molecular_graphics    'PLATON (Spek, 2003)'
_computing_publication_material  'SHELXTL (1998)'

_refine_special_details          
; 
 Refinement of F² against ALL reflections.  The weighted R-factor wR and 
 goodness of fit S are based on F², conventional R-factors R are based 
 on F, with F set to zero for negative F². The threshold expression of 
 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is 
 not relevant to the choice of reflections for refinement.  R-factors based 
 on F² are statistically about twice as large as those based on F, and R- 
 factors based on ALL data will be even larger. 
;

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0427P)²+3.5223P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         4866
_refine_ls_number_parameters     379
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0444
_refine_ls_R_factor_gt           0.0387
_refine_ls_wR_factor_ref         0.1035
_refine_ls_wR_factor_gt          0.1002
_refine_ls_goodness_of_fit_ref   1.047
_refine_ls_restrained_S_all      1.047
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
Cu1 Cu 0.50051(6) 0.36055(3) 0.00064(2) 0.02130(12) Uani 1 1 d . . .
Cu2 Cu 0.53123(6) 0.53163(3) 0.18666(2) 0.02090(12) Uani 1 1 d . . .
O1 O 0.4528(4) 0.2431(2) 0.07905(13) 0.0262(5) Uani 1 1 d . . .
O1W O 0.8412(4) 0.3758(3) 0.04170(17) 0.0401(7) Uani 1 1 d . . .
H2 H 0.8777 0.3684 0.0901 0.060 Uiso 1 1 d R . .
H3 H 0.9202 0.3434 0.0124 0.060 Uiso 1 1 d R . .
O2 O 0.5756(4) 0.3602(2) 0.19281(14) 0.0283(6) Uani 1 1 d . . .
O2W O 0.2023(4) 0.4843(3) 0.2055(3) 0.0617(10) Uani 1 1 d . . .
H4 H 0.1238 0.5220 0.2323 0.093 Uiso 1 1 d R . .
H5 H 0.2116 0.4157 0.2244 0.093 Uiso 1 1 d R . .
O3 O 0.4976(4) -0.2924(2) 0.19366(14) 0.0280(6) Uani 1 1 d . . .
O3W O 0.4440(3) 0.50628(19) 0.07095(12) 0.0198(5) Uani 1 1 d . . .
H1 H 0.3317 0.5096 0.0874 0.030 Uiso 1 1 d R . .
O4 O 0.4622(4) -0.2191(2) 0.07470(13) 0.0287(6) Uani 1 1 d . . .
O5 O 0.6801(5) -0.0321(3) 0.43349(16) 0.0497(9) Uani 1 1 d . . .
O6 O 0.7192(5) 0.1740(3) 0.43862(16) 0.0495(9) Uani 1 1 d . . .
O7 O 0.1259(4) 0.4210(2) -0.15359(16) 0.0345(6) Uani 1 1 d . . .
O8 O 0.1488(4) 0.3254(3) -0.04340(15) 0.0386(7) Uani 1 1 d . . .
O9 O 0.0950(6) -0.1382(3) -0.0782(2) 0.0686(11) Uani 1 1 d . . .
O10 O -0.0540(6) -0.2397(3) -0.1880(2) 0.0658(11) Uani 1 1 d . . .
O11 O -0.1799(5) -0.0226(3) -0.42039(16) 0.0486(8) Uani 1 1 d . . .
O12 O -0.1402(6) 0.1834(3) -0.41085(17) 0.0544(9) Uani 1 1 d . . .
N1 N 0.6088(4) 0.5608(2) 0.30760(16) 0.0232(6) Uani 1 1 d . . .
N2 N 0.9747(10) 0.4937(6) 0.4611(4) 0.122(3) Uani 1 1 d . . .
C1 C 0.4976(7) 0.6249(4) 0.3530(2) 0.0414(10) Uani 1 1 d . . .
H1A H 0.3881 0.6542 0.3303 0.050 Uiso 1 1 calc R . .
C2 C 0.5484(14) 0.6473(6) 0.4349(3) 0.094(3) Uani 1 1 d . . .
H2A H 0.4712 0.6928 0.4662 0.113 Uiso 1 1 calc R . .
C3 C 0.7615(6) 0.5189(4) 0.3434(2) 0.0355(9) Uani 1 1 d . . .
H3A H 0.8395 0.4729 0.3129 0.043 Uiso 1 1 calc R . .
C4 C 0.8066(8) 0.5427(5) 0.4257(3) 0.0611(16) Uani 1 1 d . . .
C5 C 0.7044(13) 0.6059(6) 0.4712(3) 0.088(2) Uani 1 1 d . . .
H5A H 0.7366 0.6223 0.5261 0.105 Uiso 1 1 calc R . .
C6 C 0.5162(5) 0.2592(3) 0.15134(19) 0.0203(7) Uani 1 1 d . . .
C7 C 0.5264(5) 0.1444(3) 0.19389(19) 0.0197(6) Uani 1 1 d . . .
C8 C 0.4886(5) 0.0259(3) 0.15188(18) 0.0185(6) Uani 1 1 d . . .
H8A H 0.4521 0.0165 0.0972 0.022 Uiso 1 1 calc R . .
C9 C 0.5056(5) -0.0783(3) 0.19225(18) 0.0172(6) Uani 1 1 d . . .
C10 C 0.4841(5) -0.2075(3) 0.14947(18) 0.0172(6) Uani 1 1 d . . .
C11 C 0.5598(5) -0.0631(3) 0.27385(19) 0.0202(7) Uani 1 1 d . . .
H11A H 0.5698 -0.1324 0.3010 0.024 Uiso 1 1 calc R . .
C12 C 0.5992(5) 0.0551(3) 0.31545(19) 0.0215(7) Uani 1 1 d . . .
C13 C 0.5821(5) 0.1591(3) 0.27537(19) 0.0215(7) Uani 1 1 d . . .
H13A H 0.6079 0.2381 0.3031 0.026 Uiso 1 1 calc R . .
C14 C 0.6700(6) 0.0668(3) 0.4014(2) 0.0287(8) Uani 1 1 d . . .
C15 C 0.1089(5) 0.3248(4) -0.1174(2) 0.0277(8) Uani 1 1 d . . .
C16 C 0.0433(5) 0.2020(3) -0.1670(2) 0.0246(7) Uani 1 1 d . . .
C17 C 0.0472(5) 0.0915(3) -0.1330(2) 0.0286(8) Uani 1 1 d . . .
H17A H 0.0852 0.0930 -0.0788 0.034 Uiso 1 1 calc R . .
C18 C -0.0057(5) -0.0212(3) -0.1801(2) 0.0304(8) Uani 1 1 d . . .
C19 C 0.0056(7) -0.1435(4) -0.1493(3) 0.0451(11) Uani 1 1 d . . .
C20 C -0.0640(5) -0.0241(3) -0.2611(2) 0.0291(8) Uani 1 1 d . . .
H20A H -0.0994 -0.0997 -0.2926 0.035 Uiso 1 1 calc R . .
C21 C -0.0689(5) 0.0863(3) -0.2946(2) 0.0254(7) Uani 1 1 d . . .
C22 C -0.1334(6) 0.0822(4) -0.3810(2) 0.0317(8) Uani 1 1 d . . .
C23 C -0.0146(5) 0.1992(3) -0.2480(2) 0.0256(7) Uani 1 1 d . . .
H23A H -0.0170 0.2730 -0.2709 0.031 Uiso 1 1 calc R . .


_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 O1 1.952(2) . ?
Cu1 O4 1.953(2) 2_655 ?
Cu1 O3W 1.982(2) . ?
Cu1 O3W 2.002(2) 2_665 ?
Cu1 O1W 2.392(3) . ?
Cu1 Cu1 3.0477(8) 2_665 ?
Cu2 O2 1.943(2) . ?
Cu2 O3 1.956(2) 1_565 ?
Cu2 O3W 1.981(2) . ?
Cu2 N1 2.052(3) . ?
Cu2 O2W 2.331(3) . ?
Cu2 H1 2.0648 . ?
O1 C6 1.252(4) . ?
O1W H2 0.8498 . ?
O1W H3 0.8502 . ?
O2 C6 1.252(4) . ?
O2W H4 0.8500 . ?
O2W H5 0.8500 . ?
O3 C10 1.254(4) . ?
O3 Cu2 1.955(2) 1_545 ?
O3W Cu1 2.003(2) 2_665 ?
O3W H1 0.8500 . ?
O4 C10 1.250(4) . ?
O4 Cu1 1.953(2) 2_655 ?
O5 C14 1.262(4) . ?
O6 C14 1.267(4) . ?
O7 C15 1.265(5) . ?
O8 C15 1.257(4) . ?
O9 C19 1.300(5) . ?
O10 C19 1.190(6) . ?
O11 C22 1.257(5) . ?
O12 C22 1.264(5) . ?
N1 C3 1.331(5) . ?
N1 C1 1.335(5) . ?
N2 N2 1.320(12) 2_766 ?
N2 C4 1.453(8) . ?
C1 C2 1.389(7) . ?
C1 H1A 0.9300 . ?
C2 C5 1.349(11) . ?
C2 H2A 0.9300 . ?
C3 C4 1.390(7) . ?
C3 H3A 0.9300 . ?
C4 C5 1.288(10) . ?
C5 H5A 0.9300 . ?
C6 C7 1.512(4) . ?
C7 C13 1.387(4) . ?
C7 C8 1.396(4) . ?
C8 C9 1.396(4) . ?
C8 H8A 0.9300 . ?
C9 C11 1.387(4) . ?
C9 C10 1.503(4) . ?
C11 C12 1.392(4) . ?
C11 H11A 0.9300 . ?
C12 C13 1.390(4) . ?
C12 C14 1.482(4) . ?
C13 H13A 0.9300 . ?
C15 C16 1.507(5) . ?
C16 C17 1.389(5) . ?
C16 C23 1.390(5) . ?
C17 C18 1.389(5) . ?
C17 H17A 0.9300 . ?
C18 C20 1.392(5) . ?
C18 C19 1.489(5) . ?
C20 C21 1.385(5) . ?
C20 H20A 0.9300 . ?
C21 C23 1.389(5) . ?
C21 C22 1.486(5) . ?
C23 H23A 0.9300 . ?

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 Cu1 O4 87.36(10) . 2_655 ?
O1 Cu1 O3W 94.87(9) . . ?
O4 Cu1 O3W 175.22(10) 2_655 . ?
O1 Cu1 O3W 174.50(9) . 2_665 ?
O4 Cu1 O3W 97.73(9) 2_655 2_665 ?
O3W Cu1 O3W 80.22(10) . 2_665 ?
O1 Cu1 O1W 88.33(11) . . ?
O4 Cu1 O1W 86.97(11) 2_655 . ?
O3W Cu1 O1W 97.31(10) . . ?
O3W Cu1 O1W 89.85(10) 2_665 . ?
O1 Cu1 Cu1 135.17(7) . 2_665 ?
O4 Cu1 Cu1 137.44(7) 2_655 2_665 ?
O3W Cu1 Cu1 40.35(6) . 2_665 ?
O3W Cu1 Cu1 39.86(6) 2_665 2_665 ?
O1W Cu1 Cu1 94.65(7) . 2_665 ?
O2 Cu2 O3 173.33(10) . 1_565 ?
O2 Cu2 O3W 94.63(9) . . ?
O3 Cu2 O3W 92.04(9) 1_565 . ?
O2 Cu2 N1 86.85(10) . . ?
O3 Cu2 N1 86.50(10) 1_565 . ?
O3W Cu2 N1 177.20(11) . . ?
O2 Cu2 O2W 91.47(11) . . ?
O3 Cu2 O2W 89.28(11) 1_565 . ?
O3W Cu2 O2W 85.38(13) . . ?
N1 Cu2 O2W 92.21(14) . . ?
O2 Cu2 H1 100.2 . . ?
O3 Cu2 H1 86.0 1_565 . ?
O3W Cu2 H1 24.1 . . ?
N1 Cu2 H1 153.2 . . ?
O2W Cu2 H1 62.0 . . ?
C6 O1 Cu1 126.0(2) . . ?
Cu1 O1W H2 119.5 . . ?
Cu1 O1W H3 121.9 . . ?
H2 O1W H3 107.7 . . ?
C6 O2 Cu2 134.7(2) . . ?
Cu2 O2W H4 133.1 . . ?
Cu2 O2W H5 96.8 . . ?
H4 O2W H5 107.7 . . ?
C10 O3 Cu2 140.1(2) . 1_545 ?
Cu2 O3W Cu1 121.87(11) . . ?
Cu2 O3W Cu1 121.85(11) . 2_665 ?
Cu1 O3W Cu1 99.78(10) . 2_665 ?
Cu2 O3W H1 83.5 . . ?
Cu1 O3W H1 121.1 . . ?
Cu1 O3W H1 109.4 2_665 . ?
C10 O4 Cu1 128.9(2) . 2_655 ?
C3 N1 C1 118.1(3) . . ?
C3 N1 Cu2 124.1(3) . . ?
C1 N1 Cu2 117.8(3) . . ?
N2 N2 C4 123.3(11) 2_766 . ?
N1 C1 C2 118.9(5) . . ?
N1 C1 H1A 120.6 . . ?
C2 C1 H1A 120.6 . . ?
C5 C2 C1 123.0(6) . . ?
C5 C2 H2A 118.5 . . ?
C1 C2 H2A 118.5 . . ?
N1 C3 C4 121.1(5) . . ?
N1 C3 H3A 119.4 . . ?
C4 C3 H3A 119.4 . . ?
C5 C4 C3 122.4(5) . . ?
C5 C4 N2 119.3(6) . . ?
C3 C4 N2 118.4(6) . . ?
C4 C5 C2 116.5(5) . . ?
C4 C5 H5A 121.8 . . ?
C2 C5 H5A 121.8 . . ?
O1 C6 O2 127.3(3) . . ?
O1 C6 C7 117.1(3) . . ?
O2 C6 C7 115.6(3) . . ?
C13 C7 C8 120.4(3) . . ?
C13 C7 C6 118.6(3) . . ?
C8 C7 C6 121.0(3) . . ?
C9 C8 C7 119.8(3) . . ?
C9 C8 H8A 120.1 . . ?
C7 C8 H8A 120.1 . . ?
C11 C9 C8 119.6(3) . . ?
C11 C9 C10 117.8(3) . . ?
C8 C9 C10 122.4(3) . . ?
O4 C10 O3 126.9(3) . . ?
O4 C10 C9 117.7(3) . . ?
O3 C10 C9 115.3(3) . . ?
C9 C11 C12 120.5(3) . . ?
C9 C11 H11A 119.7 . . ?
C12 C11 H11A 119.7 . . ?
C13 C12 C11 120.0(3) . . ?
C13 C12 C14 121.5(3) . . ?
C11 C12 C14 118.4(3) . . ?
C12 C13 C7 119.8(3) . . ?
C12 C13 H13A 120.1 . . ?
C7 C13 H13A 120.1 . . ?
O5 C14 O6 123.3(3) . . ?
O5 C14 C12 117.6(3) . . ?
O6 C14 C12 119.1(3) . . ?
O8 C15 O7 123.9(3) . . ?
O8 C15 C16 118.5(3) . . ?
O7 C15 C16 117.6(3) . . ?
C17 C16 C23 119.7(3) . . ?
C17 C16 C15 120.5(3) . . ?
C23 C16 C15 119.7(3) . . ?
C16 C17 C18 119.9(3) . . ?
C16 C17 H17A 120.0 . . ?
C18 C17 H17A 120.0 . . ?
C20 C18 C17 120.4(3) . . ?
C20 C18 C19 116.4(4) . . ?
C17 C18 C19 123.2(3) . . ?
O10 C19 O9 121.9(4) . . ?
O10 C19 C18 122.9(4) . . ?
O9 C19 C18 115.1(4) . . ?
C21 C20 C18 119.5(3) . . ?
C21 C20 H20A 120.3 . . ?
C18 C20 H20A 120.3 . . ?
C20 C21 C23 120.4(3) . . ?
C20 C21 C22 119.0(3) . . ?
C23 C21 C22 120.6(3) . . ?
O11 C22 O12 123.5(3) . . ?
O11 C22 C21 117.8(3) . . ?
O12 C22 C21 118.7(3) . . ?
C21 C23 C16 120.1(3) . . ?
C21 C23 H23A 120.0 . . ?
C16 C23 H23A 120.0 . . ?

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
O4 Cu1 O1 C6 137.9(3) 2_655 . . . ?
O3W Cu1 O1 C6 -46.3(3) . . . . ?
O3W Cu1 O1 C6 -19.8(12) 2_665 . . . ?
O1W Cu1 O1 C6 50.9(3) . . . . ?
Cu1 Cu1 O1 C6 -44.1(3) 2_665 . . . ?
O3 Cu2 O2 C6 160.7(9) 1_565 . . . ?
O3W Cu2 O2 C6 -21.2(3) . . . . ?
N1 Cu2 O2 C6 156.4(3) . . . . ?
O2W Cu2 O2 C6 64.3(4) . . . . ?
O2 Cu2 O3W Cu1 -18.01(15) . . . . ?
O3 Cu2 O3W Cu1 161.76(14) 1_565 . . . ?
N1 Cu2 O3W Cu1 -140(2) . . . . ?
O2W Cu2 O3W Cu1 -109.12(15) . . . . ?
O2 Cu2 O3W Cu1 -146.45(14) . . . 2_665 ?
O3 Cu2 O3W Cu1 33.33(15) 1_565 . . 2_665 ?
N1 Cu2 O3W Cu1 92(2) . . . 2_665 ?
O2W Cu2 O3W Cu1 122.44(15) . . . 2_665 ?
O1 Cu1 O3W Cu2 39.98(15) . . . . ?
O4 Cu1 O3W Cu2 157.5(11) 2_655 . . . ?
O3W Cu1 O3W Cu2 -137.53(19) 2_665 . . . ?
O1W Cu1 O3W Cu2 -48.95(15) . . . . ?
Cu1 Cu1 O3W Cu2 -137.53(19) 2_665 . . . ?
O1 Cu1 O3W Cu1 177.52(11) . . . 2_665 ?
O4 Cu1 O3W Cu1 -64.9(12) 2_655 . . 2_665 ?
O3W Cu1 O3W Cu1 0.000(2) 2_665 . . 2_665 ?
O1W Cu1 O3W Cu1 88.58(11) . . . 2_665 ?
O2 Cu2 N1 C3 44.9(3) . . . . ?
O3 Cu2 N1 C3 -134.6(3) 1_565 . . . ?
O3W Cu2 N1 C3 166.8(19) . . . . ?
O2W Cu2 N1 C3 136.3(3) . . . . ?
O2 Cu2 N1 C1 -134.5(3) . . . . ?
O3 Cu2 N1 C1 46.0(3) 1_565 . . . ?
O3W Cu2 N1 C1 -13(2) . . . . ?
O2W Cu2 N1 C1 -43.1(3) . . . . ?
C3 N1 C1 C2 1.4(6) . . . . ?
Cu2 N1 C1 C2 -179.2(4) . . . . ?
N1 C1 C2 C5 -0.7(9) . . . . ?
C1 N1 C3 C4 -1.0(6) . . . . ?
Cu2 N1 C3 C4 179.6(3) . . . . ?
N1 C3 C4 C5 -0.1(8) . . . . ?
N1 C3 C4 N2 179.7(4) . . . . ?
N2 N2 C4 C5 2.9(11) 2_766 . . . ?
N2 N2 C4 C3 -177.0(7) 2_766 . . . ?
C3 C4 C5 C2 0.8(9) . . . . ?
N2 C4 C5 C2 -179.0(6) . . . . ?
C1 C2 C5 C4 -0.4(10) . . . . ?
Cu1 O1 C6 O2 20.6(5) . . . . ?
Cu1 O1 C6 C7 -158.3(2) . . . . ?
Cu2 O2 C6 O1 23.4(6) . . . . ?
Cu2 O2 C6 C7 -157.6(2) . . . . ?
O1 C6 C7 C13 -175.2(3) . . . . ?
O2 C6 C7 C13 5.7(5) . . . . ?
O1 C6 C7 C8 7.4(5) . . . . ?
O2 C6 C7 C8 -171.7(3) . . . . ?
C13 C7 C8 C9 0.4(5) . . . . ?
C6 C7 C8 C9 177.8(3) . . . . ?
C7 C8 C9 C11 0.1(5) . . . . ?
C7 C8 C9 C10 -174.5(3) . . . . ?
Cu1 O4 C10 O3 -15.4(5) 2_655 . . . ?
Cu1 O4 C10 C9 161.8(2) 2_655 . . . ?
Cu2 O3 C10 O4 11.0(6) 1_545 . . . ?
Cu2 O3 C10 C9 -166.2(3) 1_545 . . . ?
C11 C9 C10 O4 -170.2(3) . . . . ?
C8 C9 C10 O4 4.5(5) . . . . ?
C11 C9 C10 O3 7.3(4) . . . . ?
C8 C9 C10 O3 -178.0(3) . . . . ?
C8 C9 C11 C12 -0.7(5) . . . . ?
C10 C9 C11 C12 174.2(3) . . . . ?
C9 C11 C12 C13 0.8(5) . . . . ?
C9 C11 C12 C14 -175.7(3) . . . . ?
C11 C12 C13 C7 -0.2(5) . . . . ?
C14 C12 C13 C7 176.1(3) . . . . ?
C8 C7 C13 C12 -0.4(5) . . . . ?
C6 C7 C13 C12 -177.8(3) . . . . ?
C13 C12 C14 O5 179.5(4) . . . . ?
C11 C12 C14 O5 -4.1(5) . . . . ?
C13 C12 C14 O6 -1.2(6) . . . . ?
C11 C12 C14 O6 175.2(4) . . . . ?
O8 C15 C16 C17 -6.8(5) . . . . ?
O7 C15 C16 C17 171.1(3) . . . . ?
O8 C15 C16 C23 175.6(3) . . . . ?
O7 C15 C16 C23 -6.5(5) . . . . ?
C23 C16 C17 C18 0.4(5) . . . . ?
C15 C16 C17 C18 -177.3(3) . . . . ?
C16 C17 C18 C20 -0.5(6) . . . . ?
C16 C17 C18 C19 176.3(4) . . . . ?
C20 C18 C19 O10 -9.1(7) . . . . ?
C17 C18 C19 O10 173.9(5) . . . . ?
C20 C18 C19 O9 167.4(4) . . . . ?
C17 C18 C19 O9 -9.5(7) . . . . ?
C17 C18 C20 C21 0.0(6) . . . . ?
C19 C18 C20 C21 -177.0(4) . . . . ?
C18 C20 C21 C23 0.5(6) . . . . ?
C18 C20 C21 C22 -179.4(3) . . . . ?
C20 C21 C22 O11 -0.5(6) . . . . ?
C23 C21 C22 O11 179.6(4) . . . . ?
C20 C21 C22 O12 179.0(4) . . . . ?
C23 C21 C22 O12 -0.9(6) . . . . ?
C20 C21 C23 C16 -0.6(5) . . . . ?
C22 C21 C23 C16 179.2(3) . . . . ?
C17 C16 C23 C21 0.2(5) . . . . ?
C15 C16 C23 C21 177.8(3) . . . . ?

_diffrn_measured_fraction_theta_max 0.986
_diffrn_reflns_theta_full        26.00
_diffrn_measured_fraction_theta_full 0.986
_refine_diff_density_max         1.535
_refine_diff_density_min         -0.673
_refine_diff_density_rms         0.091




####################################################################### 
# 
# 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_lm-2
_database_code_depnum_ccdc_archive 'CCDC 1050968'
_audit_update_record             
;
2015-05-21 deposited with the CCDC.
2015-06-26 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C19 H16 Cu2 N4 O10, H2 O'
_chemical_formula_sum            'C19 H18 Cu2 N4 O11'
_chemical_formula_weight         605.45

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'
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'
O O 0.0106 0.0060 '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/c'
_space_group_name_Hall           '-P 2ybc'

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

_cell_length_a                   10.7720(4)
_cell_length_b                   21.7524(9)
_cell_length_c                   9.8578(4)
_cell_angle_alpha                90.00
_cell_angle_beta                 111.7280(10)
_cell_angle_gamma                90.00
_cell_volume                     2145.74(15)
_cell_formula_units_Z            4
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    ?
_cell_measurement_theta_min      1.87
_cell_measurement_theta_max      28.32

_exptl_crystal_description       BLOCK
_exptl_crystal_colour            GREEN
_exptl_crystal_size_max          0.13
_exptl_crystal_size_mid          0.12
_exptl_crystal_size_min          0.11
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.874
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1224
_exptl_absorpt_coefficient_mu    2.055
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.766
_exptl_absorpt_correction_T_max  0.798
_exptl_absorpt_process_details   SADABS

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      296(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            15721
_diffrn_reflns_av_R_equivalents  0.0262
_diffrn_reflns_av_sigmaI/netI    0.0309
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_k_min       -28
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_theta_min         1.87
_diffrn_reflns_theta_max         28.32
_reflns_number_total             5333
_reflns_number_gt                4364
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'SMART (Bruker, 2001)'
_computing_cell_refinement       'SMART (Bruker, 2001)'
_computing_data_reduction        'SAINT+ (Bruker, 1999)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_molecular_graphics    'PLATON (Spek, 2003)'
_computing_publication_material  'SHELXTL (1998)'

_refine_special_details          
; 
 Refinement of F² against ALL reflections.  The weighted R-factor wR and 
 goodness of fit S are based on F², conventional R-factors R are based 
 on F, with F set to zero for negative F². The threshold expression of 
 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is 
 not relevant to the choice of reflections for refinement.  R-factors based 
 on F² are statistically about twice as large as those based on F, and R- 
 factors based on ALL data will be even larger. 
;

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0463P)²+2.1110P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         5333
_refine_ls_number_parameters     325
_refine_ls_number_restraints     6
_refine_ls_R_factor_all          0.0452
_refine_ls_R_factor_gt           0.0330
_refine_ls_wR_factor_ref         0.0904
_refine_ls_wR_factor_gt          0.0849
_refine_ls_goodness_of_fit_ref   1.030
_refine_ls_restrained_S_all      1.031
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
Cu1 Cu 0.96344(3) 0.110051(14) 0.56382(3) 0.01618(9) Uani 1 1 d . . .
Cu2 Cu 0.50815(3) -0.134123(14) 1.00403(3) 0.01616(8) Uani 1 1 d . . .
O1 O 0.78966(17) 0.08348(8) 0.5545(2) 0.0217(4) Uani 1 1 d . . .
O1W O 0.99975(19) 0.12817(10) 0.7760(2) 0.0292(4) Uani 1 1 d . . .
H1WA H 1.0154 0.1628 0.8191 0.035 Uiso 1 1 d R . .
H1WB H 0.9316 0.1128 0.7872 0.035 Uiso 1 1 d R . .
O2 O 0.66691(19) 0.16845(9) 0.4792(2) 0.0276(4) Uani 1 1 d . . .
O2W O 0.9140(2) 0.21268(10) 0.5207(3) 0.0386(5) Uani 1 1 d . . .
H2WA H 0.8500 0.2375 0.4803 0.046 Uiso 1 1 d R . .
H2WB H 0.9835 0.2339 0.5652 0.058 Uiso 1 1 d R . .
O3 O 0.15527(17) 0.10078(9) 0.62115(19) 0.0227(4) Uani 1 1 d . . .
O3W O 0.70654(17) -0.12546(9) 1.0809(2) 0.0229(4) Uani 1 1 d . . .
H3WA H 0.7510 -0.0955 1.0671 0.027 Uiso 1 1 d R . .
H3WB H 0.7378 -0.1337 1.1716 0.027 Uiso 1 1 d R . .
O4 O 0.1942(2) 0.15644(11) 0.4508(3) 0.0403(6) Uani 1 1 d . . .
O5 O 0.47750(18) -0.06627(9) 0.8682(2) 0.0245(4) Uani 1 1 d . . .
O6 O 0.6831(2) -0.06032(11) 0.8625(2) 0.0374(5) Uani 1 1 d . . .
O8 O 0.79962(19) 0.16548(10) -0.1349(2) 0.0305(5) Uani 1 1 d . . .
N1 N 0.9205(2) 0.08320(10) 0.3563(2) 0.0186(4) Uani 1 1 d . . .
N2 N 0.6785(2) 0.13408(10) 0.0039(2) 0.0173(4) Uani 1 1 d . . .
N3 N 0.4739(2) 0.19894(10) -0.1537(2) 0.0176(4) Uani 1 1 d . . .
N4 N 0.4851(2) 0.28784(10) -0.3476(2) 0.0220(5) Uani 1 1 d . . .
C1 C 0.8178(2) 0.11053(12) 0.2521(3) 0.0187(5) Uani 1 1 d . . .
H1A H 0.7656 0.1379 0.2803 0.022 Uiso 1 1 calc R . .
C2 C 0.7855(2) 0.10015(11) 0.1043(3) 0.0174(5) Uani 1 1 d . . .
C3 C 0.9636(3) 0.02704(15) 0.1724(3) 0.0359(7) Uani 1 1 d . . .
H3A H 1.0138 -0.0025 0.1475 0.043 Uiso 1 1 calc R . .
C4 C 0.9925(3) 0.04189(13) 0.3158(3) 0.0261(6) Uani 1 1 d . . .
H4A H 1.0643 0.0227 0.3874 0.031 Uiso 1 1 calc R . .
C5 C 0.8587(3) 0.05643(15) 0.0642(3) 0.0322(7) Uani 1 1 d . . .
H5A H 0.8381 0.0469 -0.0337 0.039 Uiso 1 1 calc R . .
C6 C 0.3710(3) 0.23664(13) -0.2159(3) 0.0259(6) Uani 1 1 d . . .
H6A H 0.2940 0.2326 -0.1950 0.031 Uiso 1 1 calc R . .
C7 C 0.3785(3) 0.28164(14) -0.3113(3) 0.0276(6) Uani 1 1 d . . .
H7A H 0.3069 0.3084 -0.3514 0.033 Uiso 1 1 calc R . .
C8 C 0.5865(3) 0.24901(12) -0.2865(3) 0.0204(5) Uani 1 1 d . . .
H8A H 0.6615 0.2516 -0.3116 0.024 Uiso 1 1 calc R . .
C9 C 0.5826(2) 0.20486(11) -0.1863(3) 0.0165(5) Uani 1 1 d . . .
C10 C 0.6989(2) 0.16427(11) -0.1029(3) 0.0180(5) Uani 1 1 d . . .
C11 C 0.6852(2) 0.11602(12) 0.5308(3) 0.0162(5) Uani 1 1 d . . .
C12 C 0.5804(2) 0.08639(11) 0.5766(3) 0.0154(5) Uani 1 1 d . . .
C13 C 0.6131(2) 0.03508(11) 0.6673(3) 0.0163(5) Uani 1 1 d . . .
H13A H 0.6971 0.0172 0.6922 0.020 Uiso 1 1 calc R . .
C14 C 0.4543(2) 0.11195(11) 0.5372(3) 0.0164(5) Uani 1 1 d . . .
H14A H 0.4315 0.1458 0.4754 0.020 Uiso 1 1 calc R . .
C15 C 0.2270(2) 0.11780(12) 0.5478(3) 0.0190(5) Uani 1 1 d . . .
C16 C 0.3608(2) 0.08726(11) 0.5896(3) 0.0156(5) Uani 1 1 d . . .
C17 C 0.3954(2) 0.03640(12) 0.6823(3) 0.0179(5) Uani 1 1 d . . .
H17A H 0.3338 0.0200 0.7181 0.021 Uiso 1 1 calc R . .
C18 C 0.5214(2) 0.01021(11) 0.7213(3) 0.0169(5) Uani 1 1 d . . .
C19 C 0.5652(2) -0.04314(12) 0.8248(3) 0.0204(5) Uani 1 1 d . . .
O4W O 0.0328(3) 0.24891(13) 0.3148(3) 0.0657(8) Uani 1 1 d U . .
H4WA H 0.1110 0.2410 0.3174 0.079 Uiso 1 1 d R . .
H4WB H 0.0016 0.2162 0.3367 0.079 Uiso 1 1 d R . .


_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 O1 1.9286(17) . ?
Cu1 O3 1.9405(17) 1_655 ?
Cu1 N1 2.010(2) . ?
Cu1 O1W 2.0193(19) . ?
Cu1 O2W 2.298(2) . ?
Cu2 O5 1.9374(18) . ?
Cu2 N2 1.983(2) 3_656 ?
Cu2 O3W 1.9945(18) . ?
Cu2 N3 1.998(2) 3_656 ?
Cu2 N4 2.313(2) 2_645 ?
O1 C11 1.275(3) . ?
O1W H1WA 0.8499 . ?
O1W H1WB 0.8501 . ?
O2 C11 1.235(3) . ?
O2W H2WA 0.8499 . ?
O2W H2WB 0.8500 . ?
O3 C15 1.293(3) . ?
O3 Cu1 1.9405(17) 1_455 ?
O3W H3WA 0.8500 . ?
O3W H3WB 0.8500 . ?
O4 C15 1.223(3) . ?
O5 C19 1.276(3) . ?
O6 C19 1.241(3) . ?
O8 C10 1.238(3) . ?
N1 C1 1.338(3) . ?
N1 C4 1.341(3) . ?
N2 C10 1.326(3) . ?
N2 C2 1.417(3) . ?
N2 Cu2 1.983(2) 3_656 ?
N3 C6 1.332(3) . ?
N3 C9 1.331(3) . ?
N3 Cu2 1.998(2) 3_656 ?
N4 C7 1.329(3) . ?
N4 C8 1.335(3) . ?
N4 Cu2 2.313(2) 2_655 ?
C1 C2 1.385(3) . ?
C1 H1A 0.9300 . ?
C2 C5 1.384(4) . ?
C3 C4 1.369(4) . ?
C3 C5 1.389(4) . ?
C3 H3A 0.9300 . ?
C4 H4A 0.9300 . ?
C5 H5A 0.9300 . ?
C6 C7 1.381(4) . ?
C6 H6A 0.9300 . ?
C7 H7A 0.9300 . ?
C8 C9 1.389(3) . ?
C8 H8A 0.9300 . ?
C9 C10 1.504(3) . ?
C11 C12 1.507(3) . ?
C12 C14 1.384(3) . ?
C12 C13 1.391(3) . ?
C13 C18 1.394(3) . ?
C13 H13A 0.9300 . ?
C14 C16 1.398(3) . ?
C14 H14A 0.9300 . ?
C15 C16 1.499(3) . ?
C16 C17 1.395(3) . ?
C17 C18 1.389(3) . ?
C17 H17A 0.9300 . ?
C18 C19 1.501(3) . ?
O4W H4WA 0.8500 . ?
O4W H4WB 0.8500 . ?

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 Cu1 O3 153.24(8) . 1_655 ?
O1 Cu1 N1 90.61(8) . . ?
O3 Cu1 N1 94.90(8) 1_655 . ?
O1 Cu1 O1W 85.42(8) . . ?
O3 Cu1 O1W 86.65(8) 1_655 . ?
N1 Cu1 O1W 173.91(9) . . ?
O1 Cu1 O2W 97.36(8) . . ?
O3 Cu1 O2W 107.67(8) 1_655 . ?
N1 Cu1 O2W 98.27(8) . . ?
O1W Cu1 O2W 86.83(8) . . ?
O5 Cu2 N2 93.53(8) . 3_656 ?
O5 Cu2 O3W 94.30(8) . . ?
N2 Cu2 O3W 160.58(8) 3_656 . ?
O5 Cu2 N3 173.37(8) . 3_656 ?
N2 Cu2 N3 81.32(8) 3_656 3_656 ?
O3W Cu2 N3 89.36(8) . 3_656 ?
O5 Cu2 N4 97.91(8) . 2_645 ?
N2 Cu2 N4 104.83(8) 3_656 2_645 ?
O3W Cu2 N4 91.64(8) . 2_645 ?
N3 Cu2 N4 87.49(8) 3_656 2_645 ?
C11 O1 Cu1 128.11(16) . . ?
Cu1 O1W H1WA 128.1 . . ?
Cu1 O1W H1WB 102.2 . . ?
H1WA O1W H1WB 107.7 . . ?
Cu1 O2W H2WA 142.7 . . ?
Cu1 O2W H2WB 109.5 . . ?
H2WA O2W H2WB 107.7 . . ?
C15 O3 Cu1 126.89(16) . 1_455 ?
Cu2 O3W H3WA 126.9 . . ?
Cu2 O3W H3WB 109.3 . . ?
H3WA O3W H3WB 107.7 . . ?
C19 O5 Cu2 125.05(16) . . ?
C1 N1 C4 118.3(2) . . ?
C1 N1 Cu1 117.78(17) . . ?
C4 N1 Cu1 123.86(18) . . ?
C10 N2 C2 118.8(2) . . ?
C10 N2 Cu2 115.59(17) . 3_656 ?
C2 N2 Cu2 125.33(16) . 3_656 ?
C6 N3 C9 119.1(2) . . ?
C6 N3 Cu2 127.66(17) . 3_656 ?
C9 N3 Cu2 113.15(17) . 3_656 ?
C7 N4 C8 117.3(2) . . ?
C7 N4 Cu2 119.83(18) . 2_655 ?
C8 N4 Cu2 122.86(17) . 2_655 ?
N1 C1 C2 123.4(2) . . ?
N1 C1 H1A 118.3 . . ?
C2 C1 H1A 118.3 . . ?
C5 C2 C1 117.7(2) . . ?
C5 C2 N2 124.1(2) . . ?
C1 C2 N2 118.2(2) . . ?
C4 C3 C5 119.6(3) . . ?
C4 C3 H3A 120.2 . . ?
C5 C3 H3A 120.2 . . ?
N1 C4 C3 122.0(3) . . ?
N1 C4 H4A 119.0 . . ?
C3 C4 H4A 119.0 . . ?
C2 C5 C3 119.0(3) . . ?
C2 C5 H5A 120.5 . . ?
C3 C5 H5A 120.5 . . ?
N3 C6 C7 120.1(2) . . ?
N3 C6 H6A 120.0 . . ?
C7 C6 H6A 120.0 . . ?
N4 C7 C6 122.0(3) . . ?
N4 C7 H7A 119.0 . . ?
C6 C7 H7A 119.0 . . ?
N4 C8 C9 121.5(2) . . ?
N4 C8 H8A 119.2 . . ?
C9 C8 H8A 119.2 . . ?
N3 C9 C8 119.9(2) . . ?
N3 C9 C10 116.1(2) . . ?
C8 C9 C10 123.8(2) . . ?
O8 C10 N2 129.2(2) . . ?
O8 C10 C9 118.6(2) . . ?
N2 C10 C9 112.1(2) . . ?
O2 C11 O1 125.7(2) . . ?
O2 C11 C12 119.7(2) . . ?
O1 C11 C12 114.6(2) . . ?
C14 C12 C13 119.4(2) . . ?
C14 C12 C11 120.7(2) . . ?
C13 C12 C11 119.7(2) . . ?
C12 C13 C18 120.7(2) . . ?
C12 C13 H13A 119.7 . . ?
C18 C13 H13A 119.7 . . ?
C12 C14 C16 120.6(2) . . ?
C12 C14 H14A 119.7 . . ?
C16 C14 H14A 119.7 . . ?
O4 C15 O3 125.1(2) . . ?
O4 C15 C16 119.3(2) . . ?
O3 C15 C16 115.6(2) . . ?
C17 C16 C14 119.5(2) . . ?
C17 C16 C15 121.9(2) . . ?
C14 C16 C15 118.6(2) . . ?
C18 C17 C16 120.2(2) . . ?
C18 C17 H17A 119.9 . . ?
C16 C17 H17A 119.9 . . ?
C17 C18 C13 119.6(2) . . ?
C17 C18 C19 122.3(2) . . ?
C13 C18 C19 118.1(2) . . ?
O6 C19 O5 125.7(2) . . ?
O6 C19 C18 117.7(2) . . ?
O5 C19 C18 116.6(2) . . ?
H4WA O4W H4WB 107.7 . . ?

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
O3 Cu1 O1 C11 159.58(19) 1_655 . . . ?
N1 Cu1 O1 C11 -98.3(2) . . . . ?
O1W Cu1 O1 C11 86.4(2) . . . . ?
O2W Cu1 O1 C11 0.2(2) . . . . ?
N2 Cu2 O5 C19 -179.5(2) 3_656 . . . ?
O3W Cu2 O5 C19 18.2(2) . . . . ?
N3 Cu2 O5 C19 141.6(7) 3_656 . . . ?
N4 Cu2 O5 C19 -74.0(2) 2_645 . . . ?
O1 Cu1 N1 C1 61.68(19) . . . . ?
O3 Cu1 N1 C1 -144.54(19) 1_655 . . . ?
O1W Cu1 N1 C1 111.0(7) . . . . ?
O2W Cu1 N1 C1 -35.85(19) . . . . ?
O1 Cu1 N1 C4 -121.8(2) . . . . ?
O3 Cu1 N1 C4 32.0(2) 1_655 . . . ?
O1W Cu1 N1 C4 -72.5(8) . . . . ?
O2W Cu1 N1 C4 140.7(2) . . . . ?
C4 N1 C1 C2 -2.6(4) . . . . ?
Cu1 N1 C1 C2 174.09(19) . . . . ?
N1 C1 C2 C5 4.0(4) . . . . ?
N1 C1 C2 N2 -177.0(2) . . . . ?
C10 N2 C2 C5 -53.1(4) . . . . ?
Cu2 N2 C2 C5 120.4(3) 3_656 . . . ?
C10 N2 C2 C1 128.0(3) . . . . ?
Cu2 N2 C2 C1 -58.5(3) 3_656 . . . ?
C1 N1 C4 C3 -0.3(4) . . . . ?
Cu1 N1 C4 C3 -176.8(2) . . . . ?
C5 C3 C4 N1 1.6(5) . . . . ?
C1 C2 C5 C3 -2.5(4) . . . . ?
N2 C2 C5 C3 178.6(3) . . . . ?
C4 C3 C5 C2 -0.1(5) . . . . ?
C9 N3 C6 C7 -0.8(4) . . . . ?
Cu2 N3 C6 C7 175.9(2) 3_656 . . . ?
C8 N4 C7 C6 -0.7(4) . . . . ?
Cu2 N4 C7 C6 -178.6(2) 2_655 . . . ?
N3 C6 C7 N4 2.0(5) . . . . ?
C7 N4 C8 C9 -1.6(4) . . . . ?
Cu2 N4 C8 C9 176.18(18) 2_655 . . . ?
C6 N3 C9 C8 -1.5(4) . . . . ?
Cu2 N3 C9 C8 -178.63(18) 3_656 . . . ?
C6 N3 C9 C10 175.1(2) . . . . ?
Cu2 N3 C9 C10 -2.0(3) 3_656 . . . ?
N4 C8 C9 N3 2.7(4) . . . . ?
N4 C8 C9 C10 -173.6(2) . . . . ?
C2 N2 C10 O8 3.9(4) . . . . ?
Cu2 N2 C10 O8 -170.2(2) 3_656 . . . ?
C2 N2 C10 C9 -171.9(2) . . . . ?
Cu2 N2 C10 C9 14.0(3) 3_656 . . . ?
N3 C9 C10 O8 175.9(2) . . . . ?
C8 C9 C10 O8 -7.6(4) . . . . ?
N3 C9 C10 N2 -7.8(3) . . . . ?
C8 C9 C10 N2 168.7(2) . . . . ?
Cu1 O1 C11 O2 16.2(4) . . . . ?
Cu1 O1 C11 C12 -161.57(16) . . . . ?
O2 C11 C12 C14 12.1(4) . . . . ?
O1 C11 C12 C14 -169.9(2) . . . . ?
O2 C11 C12 C13 -163.7(2) . . . . ?
O1 C11 C12 C13 14.3(3) . . . . ?
C14 C12 C13 C18 -1.5(4) . . . . ?
C11 C12 C13 C18 174.4(2) . . . . ?
C13 C12 C14 C16 1.0(4) . . . . ?
C11 C12 C14 C16 -174.8(2) . . . . ?
Cu1 O3 C15 O4 20.7(4) 1_455 . . . ?
Cu1 O3 C15 C16 -160.08(17) 1_455 . . . ?
C12 C14 C16 C17 0.0(4) . . . . ?
C12 C14 C16 C15 178.0(2) . . . . ?
O4 C15 C16 C17 -169.7(3) . . . . ?
O3 C15 C16 C17 11.0(4) . . . . ?
O4 C15 C16 C14 12.3(4) . . . . ?
O3 C15 C16 C14 -167.0(2) . . . . ?
C14 C16 C17 C18 -0.5(4) . . . . ?
C15 C16 C17 C18 -178.5(2) . . . . ?
C16 C17 C18 C13 0.0(4) . . . . ?
C16 C17 C18 C19 177.8(2) . . . . ?
C12 C13 C18 C17 1.0(4) . . . . ?
C12 C13 C18 C19 -176.9(2) . . . . ?
Cu2 O5 C19 O6 0.0(4) . . . . ?
Cu2 O5 C19 C18 -178.82(17) . . . . ?
C17 C18 C19 O6 -174.3(3) . . . . ?
C13 C18 C19 O6 3.5(4) . . . . ?
C17 C18 C19 O5 4.6(4) . . . . ?
C13 C18 C19 O5 -177.6(2) . . . . ?

_diffrn_measured_fraction_theta_max 0.998
_diffrn_reflns_theta_full        28.32
_diffrn_measured_fraction_theta_full 0.998
_refine_diff_density_max         0.954
_refine_diff_density_min         -0.641
_refine_diff_density_rms         0.086










####################################################################### 
# 
# 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_lm-3
_database_code_depnum_ccdc_archive 'CCDC 1050969'
_audit_update_record             
;
2015-05-21 deposited with the CCDC.
2015-06-26 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C22 H14 Cu2 N2 O8'
_chemical_formula_sum            'C22 H14 Cu2 N2 O8'
_chemical_formula_weight         561.43

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'
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'
O O 0.0106 0.0060 '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/c'
_space_group_name_Hall           '-P 2ybc'

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

_cell_length_a                   10.6876(7)
_cell_length_b                   12.9221(8)
_cell_length_c                   18.5048(9)
_cell_angle_alpha                90.00
_cell_angle_beta                 123.820(3)
_cell_angle_gamma                90.00
_cell_volume                     2123.2(2)
_cell_formula_units_Z            4
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    ?
_cell_measurement_theta_min      2.06
_cell_measurement_theta_max      25.06

_exptl_crystal_description       BLOCK
_exptl_crystal_colour            GREEN
_exptl_crystal_size_max          0.13
_exptl_crystal_size_mid          0.12
_exptl_crystal_size_min          0.11
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.756
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1128
_exptl_absorpt_coefficient_mu    2.057
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.765
_exptl_absorpt_correction_T_max  0.798
_exptl_absorpt_process_details   SADABS

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      296(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            10631
_diffrn_reflns_av_R_equivalents  0.0319
_diffrn_reflns_av_sigmaI/netI    0.0376
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_theta_min         2.06
_diffrn_reflns_theta_max         25.06
_reflns_number_total             3720
_reflns_number_gt                3086
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'SMART (Bruker, 2001)'
_computing_cell_refinement       'SMART (Bruker, 2001)'
_computing_data_reduction        'SAINT+ (Bruker, 1999)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_molecular_graphics    'PLATON (Spek, 2003)'
_computing_publication_material  'SHELXTL (1998)'

_refine_special_details          
; 
 Refinement of F² against ALL reflections.  The weighted R-factor wR and 
 goodness of fit S are based on F², conventional R-factors R are based 
 on F, with F set to zero for negative F². The threshold expression of 
 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is 
 not relevant to the choice of reflections for refinement.  R-factors based 
 on F² are statistically about twice as large as those based on F, and R- 
 factors based on ALL data will be even larger. 
;

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0356P)²+1.9663P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         3720
_refine_ls_number_parameters     307
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0413
_refine_ls_R_factor_gt           0.0312
_refine_ls_wR_factor_ref         0.0767
_refine_ls_wR_factor_gt          0.0733
_refine_ls_goodness_of_fit_ref   1.031
_refine_ls_restrained_S_all      1.031
_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 0.64797(4) -0.40290(3) -0.33545(2) 0.01654(11) Uani 1 1 d . . .
Cu2 Cu 0.65200(4) -0.51625(3) -0.48649(2) 0.01574(11) Uani 1 1 d . . .
O1 O 0.8408(3) -0.3629(2) -0.32021(14) 0.0297(6) Uani 1 1 d . . .
O1W O 0.5415(2) -0.41421(15) -0.46010(12) 0.0132(4) Uani 1 1 d . . .
H1WA H 0.6313 -0.3905 -0.4342 0.016 Uiso 1 1 d R . .
O2 O 0.8287(2) -0.42956(17) -0.43641(14) 0.0232(5) Uani 1 1 d . . .
O3 O 1.2738(2) -0.41388(17) -0.44861(14) 0.0247(5) Uani 1 1 d . . .
O4 O 1.4705(2) -0.31763(16) -0.35135(13) 0.0196(5) Uani 1 1 d . . .
O5 O 1.3937(3) -0.06175(17) -0.17594(14) 0.0236(5) Uani 1 1 d . . .
O6 O 1.2452(3) -0.11395(18) -0.13351(14) 0.0276(6) Uani 1 1 d . . .
O7 O 0.5488(3) -0.2747(2) -0.01835(19) 0.0465(7) Uani 1 1 d . . .
N1 N 0.7306(3) -0.3801(2) -0.21073(16) 0.0244(6) Uani 1 1 d . . .
N2 N 0.5273(3) -0.4018(2) -0.10657(18) 0.0289(7) Uani 1 1 d . . .
H2B H 0.4838 -0.4595 -0.1306 0.035 Uiso 1 1 d R . .
C1 C 0.8312(4) -0.3060(3) -0.1651(2) 0.0337(9) Uani 1 1 d . . .
H1A H 0.8960 -0.2847 -0.1808 0.040 Uiso 1 1 calc R . .
C2 C 0.8406(5) -0.2602(3) -0.0945(2) 0.0434(10) Uani 1 1 d . . .
H2A H 0.9133 -0.2101 -0.0621 0.052 Uiso 1 1 calc R . .
C3 C 0.7430(5) -0.2888(3) -0.0726(2) 0.0419(10) Uani 1 1 d . . .
H3A H 0.7465 -0.2566 -0.0266 0.050 Uiso 1 1 calc R . .
C4 C 0.6381(4) -0.3665(3) -0.1195(2) 0.0279(8) Uani 1 1 d . . .
C5 C 0.6398(4) -0.4109(3) -0.1860(2) 0.0270(8) Uani 1 1 d . . .
H5A H 0.5743 -0.4657 -0.2158 0.032 Uiso 1 1 calc R . .
C6 C 0.4836(4) -0.3528(3) -0.0596(2) 0.0287(8) Uani 1 1 d . . .
C7 C 0.3555(4) -0.3971(3) -0.0592(2) 0.0283(8) Uani 1 1 d . . .
C8 C 0.3278(6) -0.3533(4) -0.0021(3) 0.0633(15) Uani 1 1 d . . .
H8A H 0.3865 -0.2978 0.0320 0.076 Uiso 1 1 calc R . .
C9 C 0.2161(6) -0.3893(4) 0.0061(3) 0.0639(15) Uani 1 1 d . . .
H9A H 0.2004 -0.3570 0.0453 0.077 Uiso 1 1 calc R . .
C10 C 0.1263(4) -0.4714(3) -0.0417(2) 0.0331(8) Uani 1 1 d . . .
C11 C 0.1518(5) -0.5128(4) -0.1011(3) 0.0533(12) Uani 1 1 d . . .
H11A H 0.0910 -0.5668 -0.1366 0.064 Uiso 1 1 calc R . .
C12 C 0.2638(5) -0.4771(4) -0.1099(3) 0.0523(12) Uani 1 1 d . . .
H12A H 0.2776 -0.5074 -0.1505 0.063 Uiso 1 1 calc R . .
C13 C 0.0119(4) -0.5136(3) -0.0305(2) 0.0364(9) Uani 1 1 d . . .
H13A H -0.0507 -0.5644 -0.0697 0.044 Uiso 1 1 calc R . .
C14 C 0.8902(3) -0.3778(2) -0.3672(2) 0.0192(7) Uani 1 1 d . . .
C15 C 1.0383(3) -0.3289(2) -0.33779(19) 0.0178(7) Uani 1 1 d . . .
C16 C 1.1021(3) -0.2556(2) -0.27191(19) 0.0186(7) Uani 1 1 d . . .
H16A H 1.0537 -0.2384 -0.2445 0.022 Uiso 1 1 calc R . .
C17 C 1.2365(3) -0.2076(2) -0.24621(18) 0.0160(6) Uani 1 1 d . . .
C18 C 1.2972(3) -0.1214(2) -0.17921(19) 0.0171(7) Uani 1 1 d . . .
C19 C 1.3125(3) -0.2375(2) -0.28465(19) 0.0164(6) Uani 1 1 d . . .
H19A H 1.4033 -0.2061 -0.2676 0.020 Uiso 1 1 calc R . .
C20 C 1.2527(3) -0.3146(2) -0.34852(19) 0.0162(6) Uani 1 1 d . . .
C21 C 1.3388(3) -0.3516(2) -0.38623(19) 0.0157(6) Uani 1 1 d . . .
C22 C 1.1142(3) -0.3581(2) -0.37605(19) 0.0176(7) Uani 1 1 d . . .
H22A H 1.0719 -0.4071 -0.4203 0.021 Uiso 1 1 calc R . .


_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 O1W 1.9274(19) . ?
Cu1 N1 1.981(3) . ?
Cu1 O1 1.987(2) . ?
Cu1 O4 2.068(2) 1_455 ?
Cu1 O5 2.136(2) 2_744 ?
Cu1 H1WA 1.7417 . ?
Cu2 O2 1.932(2) . ?
Cu2 O1W 1.9453(19) 3_644 ?
Cu2 O3 1.986(2) 3_744 ?
Cu2 O1W 2.0038(19) . ?
Cu2 O6 2.240(2) 2_744 ?
Cu2 Cu2 3.0288(7) 3_644 ?
Cu2 H1WA 1.9654 . ?
O1 C14 1.259(4) . ?
O1W Cu2 1.9453(19) 3_644 ?
O1W H1WA 0.8559 . ?
O2 C14 1.258(4) . ?
O3 C21 1.253(4) . ?
O3 Cu2 1.986(2) 3_744 ?
O4 C21 1.257(4) . ?
O4 Cu1 2.068(2) 1_655 ?
O5 C18 1.262(4) . ?
O5 Cu1 2.136(2) 2_754 ?
O6 C18 1.248(4) . ?
O6 Cu2 2.240(2) 2_754 ?
O7 C6 1.222(4) . ?
N1 C1 1.332(4) . ?
N1 C5 1.343(4) . ?
N2 C6 1.352(4) . ?
N2 C4 1.408(4) . ?
N2 H2B 0.8601 . ?
C1 C2 1.386(5) . ?
C1 H1A 0.9300 . ?
C2 C3 1.362(5) . ?
C2 H2A 0.9300 . ?
C3 C4 1.390(5) . ?
C3 H3A 0.9300 . ?
C4 C5 1.367(5) . ?
C5 H5A 0.9300 . ?
C6 C7 1.488(5) . ?
C7 C12 1.373(5) . ?
C7 C8 1.368(5) . ?
C8 C9 1.365(6) . ?
C8 H8A 0.9300 . ?
C9 C10 1.373(6) . ?
C9 H9A 0.9300 . ?
C10 C11 1.380(5) . ?
C10 C13 1.454(5) . ?
C11 C12 1.373(6) . ?
C11 H11A 0.9300 . ?
C12 H12A 0.9300 . ?
C13 C13 1.337(7) 3_545 ?
C13 H13A 0.9300 . ?
C14 C15 1.497(4) . ?
C15 C16 1.387(4) . ?
C15 C22 1.394(4) . ?
C16 C17 1.383(4) . ?
C16 H16A 0.9300 . ?
C17 C19 1.400(4) . ?
C17 C18 1.517(4) . ?
C19 C20 1.398(4) . ?
C19 H19A 0.9300 . ?
C20 C22 1.388(4) . ?
C20 C21 1.510(4) . ?
C22 H22A 0.9300 . ?

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
O1W Cu1 N1 171.48(10) . . ?
O1W Cu1 O1 93.71(8) . . ?
N1 Cu1 O1 92.36(10) . . ?
O1W Cu1 O4 89.21(8) . 1_455 ?
N1 Cu1 O4 82.28(10) . 1_455 ?
O1 Cu1 O4 132.72(10) . 1_455 ?
O1W Cu1 O5 91.64(8) . 2_744 ?
N1 Cu1 O5 90.58(10) . 2_744 ?
O1 Cu1 O5 119.53(10) . 2_744 ?
O4 Cu1 O5 107.52(8) 1_455 2_744 ?
O1W Cu1 H1WA 26.4 . . ?
N1 Cu1 H1WA 158.1 . . ?
O1 Cu1 H1WA 67.5 . . ?
O4 Cu1 H1WA 104.6 1_455 . ?
O5 Cu1 H1WA 106.6 2_744 . ?
O2 Cu2 O1W 172.04(9) . 3_644 ?
O2 Cu2 O3 86.61(9) . 3_744 ?
O1W Cu2 O3 98.74(8) 3_644 3_744 ?
O2 Cu2 O1W 93.05(9) . . ?
O1W Cu2 O1W 79.84(8) 3_644 . ?
O3 Cu2 O1W 159.12(9) 3_744 . ?
O2 Cu2 O6 92.41(9) . 2_744 ?
O1W Cu2 O6 92.26(8) 3_644 2_744 ?
O3 Cu2 O6 101.68(9) 3_744 2_744 ?
O1W Cu2 O6 99.19(8) . 2_744 ?
O2 Cu2 Cu2 132.17(7) . 3_644 ?
O1W Cu2 Cu2 40.63(6) 3_644 3_644 ?
O3 Cu2 Cu2 135.70(7) 3_744 3_644 ?
O1W Cu2 Cu2 39.21(5) . 3_644 ?
O6 Cu2 Cu2 97.53(6) 2_744 3_644 ?
O2 Cu2 H1WA 68.5 . . ?
O1W Cu2 H1WA 104.6 3_644 . ?
O3 Cu2 H1WA 150.0 3_744 . ?
O1W Cu2 H1WA 24.9 . . ?
O6 Cu2 H1WA 96.0 2_744 . ?
Cu2 Cu2 H1WA 64.0 3_644 . ?
C14 O1 Cu1 131.6(2) . . ?
Cu1 O1W Cu2 113.32(9) . 3_644 ?
Cu1 O1W Cu2 107.82(9) . . ?
Cu2 O1W Cu2 100.16(8) 3_644 . ?
Cu1 O1W H1WA 64.6 . . ?
Cu2 O1W H1WA 173.3 3_644 . ?
Cu2 O1W H1WA 75.1 . . ?
C14 O2 Cu2 127.87(19) . . ?
C21 O3 Cu2 130.23(19) . 3_744 ?
C21 O4 Cu1 124.25(19) . 1_655 ?
C18 O5 Cu1 112.48(19) . 2_754 ?
C18 O6 Cu2 123.9(2) . 2_754 ?
C1 N1 C5 118.5(3) . . ?
C1 N1 Cu1 121.7(2) . . ?
C5 N1 Cu1 114.5(2) . . ?
C6 N2 C4 125.6(3) . . ?
C6 N2 H2B 117.2 . . ?
C4 N2 H2B 117.2 . . ?
N1 C1 C2 121.0(3) . . ?
N1 C1 H1A 119.5 . . ?
C2 C1 H1A 119.5 . . ?
C3 C2 C1 119.9(4) . . ?
C3 C2 H2A 120.1 . . ?
C1 C2 H2A 120.1 . . ?
C2 C3 C4 119.7(3) . . ?
C2 C3 H3A 120.2 . . ?
C4 C3 H3A 120.2 . . ?
C5 C4 C3 117.0(3) . . ?
C5 C4 N2 116.8(3) . . ?
C3 C4 N2 126.2(3) . . ?
N1 C5 C4 123.8(3) . . ?
N1 C5 H5A 118.1 . . ?
C4 C5 H5A 118.1 . . ?
O7 C6 N2 120.5(3) . . ?
O7 C6 C7 121.4(3) . . ?
N2 C6 C7 118.1(3) . . ?
C12 C7 C8 117.4(4) . . ?
C12 C7 C6 126.6(3) . . ?
C8 C7 C6 116.1(3) . . ?
C9 C8 C7 121.5(4) . . ?
C9 C8 H8A 119.2 . . ?
C7 C8 H8A 119.2 . . ?
C8 C9 C10 122.2(4) . . ?
C8 C9 H9A 118.9 . . ?
C10 C9 H9A 118.9 . . ?
C9 C10 C11 115.8(4) . . ?
C9 C10 C13 122.7(3) . . ?
C11 C10 C13 121.5(4) . . ?
C12 C11 C10 122.4(4) . . ?
C12 C11 H11A 118.8 . . ?
C10 C11 H11A 118.8 . . ?
C7 C12 C11 120.7(4) . . ?
C7 C12 H12A 119.7 . . ?
C11 C12 H12A 119.7 . . ?
C13 C13 C10 126.3(5) 3_545 . ?
C13 C13 H13A 116.8 3_545 . ?
C10 C13 H13A 116.8 . . ?
O2 C14 O1 127.0(3) . . ?
O2 C14 C15 116.3(3) . . ?
O1 C14 C15 116.7(3) . . ?
C16 C15 C22 119.4(3) . . ?
C16 C15 C14 120.8(3) . . ?
C22 C15 C14 119.8(3) . . ?
C17 C16 C15 121.1(3) . . ?
C17 C16 H16A 119.4 . . ?
C15 C16 H16A 119.4 . . ?
C16 C17 C19 119.1(3) . . ?
C16 C17 C18 120.0(3) . . ?
C19 C17 C18 120.9(3) . . ?
O6 C18 O5 125.5(3) . . ?
O6 C18 C17 117.5(3) . . ?
O5 C18 C17 117.0(3) . . ?
C20 C19 C17 120.3(3) . . ?
C20 C19 H19A 119.9 . . ?
C17 C19 H19A 119.9 . . ?
C22 C20 C19 119.4(3) . . ?
C22 C20 C21 120.1(3) . . ?
C19 C20 C21 120.5(3) . . ?
O3 C21 O4 125.9(3) . . ?
O3 C21 C20 117.5(3) . . ?
O4 C21 C20 116.6(3) . . ?
C20 C22 C15 120.5(3) . . ?
C20 C22 H22A 119.8 . . ?
C15 C22 H22A 119.8 . . ?

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
O1W Cu1 O1 C14 -23.3(3) . . . . ?
N1 Cu1 O1 C14 162.7(3) . . . . ?
O4 Cu1 O1 C14 -115.6(3) 1_455 . . . ?
O5 Cu1 O1 C14 70.7(3) 2_744 . . . ?
N1 Cu1 O1W Cu2 -58.0(7) . . . 3_644 ?
O1 Cu1 O1W Cu2 166.72(11) . . . 3_644 ?
O4 Cu1 O1W Cu2 -60.52(11) 1_455 . . 3_644 ?
O5 Cu1 O1W Cu2 46.99(11) 2_744 . . 3_644 ?
N1 Cu1 O1W Cu2 -167.9(7) . . . . ?
O1 Cu1 O1W Cu2 56.83(11) . . . . ?
O4 Cu1 O1W Cu2 -170.40(9) 1_455 . . . ?
O5 Cu1 O1W Cu2 -62.90(10) 2_744 . . . ?
O2 Cu2 O1W Cu1 -64.93(10) . . . . ?
O1W Cu2 O1W Cu1 118.68(12) 3_644 . . . ?
O3 Cu2 O1W Cu1 -153.42(19) 3_744 . . . ?
O6 Cu2 O1W Cu1 28.01(11) 2_744 . . . ?
Cu2 Cu2 O1W Cu1 118.68(12) 3_644 . . . ?
O2 Cu2 O1W Cu2 176.39(9) . . . 3_644 ?
O1W Cu2 O1W Cu2 0.0 3_644 . . 3_644 ?
O3 Cu2 O1W Cu2 87.9(2) 3_744 . . 3_644 ?
O6 Cu2 O1W Cu2 -90.67(9) 2_744 . . 3_644 ?
O1W Cu2 O2 C14 68.6(7) 3_644 . . . ?
O3 Cu2 O2 C14 -158.9(3) 3_744 . . . ?
O1W Cu2 O2 C14 42.0(3) . . . . ?
O6 Cu2 O2 C14 -57.3(3) 2_744 . . . ?
Cu2 Cu2 O2 C14 45.1(3) 3_644 . . . ?
O1W Cu1 N1 C1 -101.4(7) . . . . ?
O1 Cu1 N1 C1 34.0(3) . . . . ?
O4 Cu1 N1 C1 -98.9(3) 1_455 . . . ?
O5 Cu1 N1 C1 153.5(3) 2_744 . . . ?
O1W Cu1 N1 C5 52.5(8) . . . . ?
O1 Cu1 N1 C5 -172.2(2) . . . . ?
O4 Cu1 N1 C5 55.0(2) 1_455 . . . ?
O5 Cu1 N1 C5 -52.6(2) 2_744 . . . ?
C5 N1 C1 C2 -1.1(5) . . . . ?
Cu1 N1 C1 C2 151.7(3) . . . . ?
N1 C1 C2 C3 -2.0(6) . . . . ?
C1 C2 C3 C4 2.3(6) . . . . ?
C2 C3 C4 C5 0.4(6) . . . . ?
C2 C3 C4 N2 -177.7(4) . . . . ?
C6 N2 C4 C5 -163.4(3) . . . . ?
C6 N2 C4 C3 14.7(6) . . . . ?
C1 N1 C5 C4 4.0(5) . . . . ?
Cu1 N1 C5 C4 -150.7(3) . . . . ?
C3 C4 C5 N1 -3.6(5) . . . . ?
N2 C4 C5 N1 174.7(3) . . . . ?
C4 N2 C6 O7 -5.6(5) . . . . ?
C4 N2 C6 C7 174.9(3) . . . . ?
O7 C6 C7 C12 172.4(4) . . . . ?
N2 C6 C7 C12 -8.0(6) . . . . ?
O7 C6 C7 C8 -7.8(6) . . . . ?
N2 C6 C7 C8 171.7(4) . . . . ?
C12 C7 C8 C9 1.7(8) . . . . ?
C6 C7 C8 C9 -178.1(5) . . . . ?
C7 C8 C9 C10 0.5(9) . . . . ?
C8 C9 C10 C11 -2.6(8) . . . . ?
C8 C9 C10 C13 176.9(5) . . . . ?
C9 C10 C11 C12 2.5(7) . . . . ?
C13 C10 C11 C12 -177.0(4) . . . . ?
C8 C7 C12 C11 -1.7(7) . . . . ?
C6 C7 C12 C11 178.0(4) . . . . ?
C10 C11 C12 C7 -0.4(8) . . . . ?
C9 C10 C13 C13 -6.5(8) . . . 3_545 ?
C11 C10 C13 C13 172.9(5) . . . 3_545 ?
Cu2 O2 C14 O1 -8.0(5) . . . . ?
Cu2 O2 C14 C15 172.0(2) . . . . ?
Cu1 O1 C14 O2 -4.6(5) . . . . ?
Cu1 O1 C14 C15 175.5(2) . . . . ?
O2 C14 C15 C16 168.3(3) . . . . ?
O1 C14 C15 C16 -11.8(5) . . . . ?
O2 C14 C15 C22 -12.6(4) . . . . ?
O1 C14 C15 C22 167.3(3) . . . . ?
C22 C15 C16 C17 3.0(5) . . . . ?
C14 C15 C16 C17 -178.0(3) . . . . ?
C15 C16 C17 C19 -3.2(5) . . . . ?
C15 C16 C17 C18 175.0(3) . . . . ?
Cu2 O6 C18 O5 -15.0(5) 2_754 . . . ?
Cu2 O6 C18 C17 166.87(19) 2_754 . . . ?
Cu1 O5 C18 O6 -41.9(4) 2_754 . . . ?
Cu1 O5 C18 C17 136.2(2) 2_754 . . . ?
C16 C17 C18 O6 17.7(4) . . . . ?
C19 C17 C18 O6 -164.2(3) . . . . ?
C16 C17 C18 O5 -160.6(3) . . . . ?
C19 C17 C18 O5 17.5(4) . . . . ?
C16 C17 C19 C20 0.4(4) . . . . ?
C18 C17 C19 C20 -177.8(3) . . . . ?
C17 C19 C20 C22 2.6(4) . . . . ?
C17 C19 C20 C21 -176.3(3) . . . . ?
Cu2 O3 C21 O4 1.5(5) 3_744 . . . ?
Cu2 O3 C21 C20 -177.86(19) 3_744 . . . ?
Cu1 O4 C21 O3 -35.3(4) 1_655 . . . ?
Cu1 O4 C21 C20 144.0(2) 1_655 . . . ?
C22 C20 C21 O3 7.4(4) . . . . ?
C19 C20 C21 O3 -173.7(3) . . . . ?
C22 C20 C21 O4 -172.0(3) . . . . ?
C19 C20 C21 O4 6.9(4) . . . . ?
C19 C20 C22 C15 -2.9(5) . . . . ?
C21 C20 C22 C15 176.0(3) . . . . ?
C16 C15 C22 C20 0.1(5) . . . . ?
C14 C15 C22 C20 -179.0(3) . . . . ?

_diffrn_measured_fraction_theta_max 0.999
_diffrn_reflns_theta_full        25.06
_diffrn_measured_fraction_theta_full 0.999
_refine_diff_density_max         0.645
_refine_diff_density_min         -0.889
_refine_diff_density_rms         0.079







