# Supplementary Material (ESI) for CrystEngComm
# This journal is (c) The Royal Society of Chemistry 2009

data_global
_journal_name_full               CrystEngComm

_journal_coden_Cambridge         1350

_publ_contact_author_name        'Robert LaDuca'
_publ_contact_author_email       LADUCA@MSU.EDU

_publ_section_title              
;
Structure and Physical Properties of Substituted
Malonate Divalent Metal Coordination Polymers with Dipyridylamine
Co-Ligands: Acentric Chain, Herringbone Layer, and Novel Binodal
Network Topologies
;
loop_
_publ_author_name
'Robert LaDuca'
'Gregory A. Farnum'
'Joseph A. Nettleman'

# Attachment '0cummaldpafinal.cif'

data_pca21
_database_code_depnum_ccdc_archive 'CCDC 735595'

_audit_update_record             
;
2009-10-08 # Formatted by publCIF
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C18 H21 Cu N3 O9'
_chemical_formula_weight         486.92

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cu Cu 0.3201 1.2651 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_H-M   Pca2(1)

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

_cell_length_a                   20.258(3)
_cell_length_b                   4.7728(6)
_cell_length_c                   21.145(3)
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_volume                     2044.4(5)
_cell_formula_units_Z            4
_cell_measurement_temperature    173(2)
_cell_measurement_reflns_used    21029
_cell_measurement_theta_min      1.93
_cell_measurement_theta_max      28.15

_exptl_crystal_description       block
_exptl_crystal_colour            blue
_exptl_crystal_size_max          0.50
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.15
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.582
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1004
_exptl_absorpt_coefficient_mu    1.125
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.6031
_exptl_absorpt_correction_T_max  0.8494
_exptl_absorpt_process_details   SADABS

_exptl_special_details           
;
?
;

_diffrn_ambient_temperature      173(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  ?
_diffrn_measurement_method       ?
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            21029
_diffrn_reflns_av_R_equivalents  0.0403
_diffrn_reflns_av_sigmaI/netI    0.0399
_diffrn_reflns_limit_h_min       -26
_diffrn_reflns_limit_h_max       26
_diffrn_reflns_limit_k_min       -6
_diffrn_reflns_limit_k_max       6
_diffrn_reflns_limit_l_min       -27
_diffrn_reflns_limit_l_max       27
_diffrn_reflns_theta_min         1.93
_diffrn_reflns_theta_max         28.15
_reflns_number_total             4688
_reflns_number_gt                4084
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_molecular_graphics    ?
_computing_publication_material  ?

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

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[\s^2^(Fo^2^)+(0.0435P)^2^+1.0379P] where P=(Fo^2^+2Fc^2^)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0.021(14)
_refine_ls_number_reflns         4688
_refine_ls_number_parameters     292
_refine_ls_number_restraints     6
_refine_ls_R_factor_all          0.0430
_refine_ls_R_factor_gt           0.0339
_refine_ls_wR_factor_ref         0.0870
_refine_ls_wR_factor_gt          0.0830
_refine_ls_goodness_of_fit_ref   1.058
_refine_ls_restrained_S_all      1.062
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
Cu1 Cu 0.046480(13) 1.00665(7) 0.22680(3) 0.01478(9) Uani 1 1 d . . .
O1 O 0.10191(11) 1.0601(5) 0.30102(11) 0.0237(5) Uani 1 1 d . . .
O1W O -0.0565(3) 0.8340(17) -0.0660(2) 0.131(2) Uani 1 1 d D . .
H1WA H -0.093(2) 0.865(9) -0.0389(19) 0.158 Uiso 1 1 d D . .
H1WB H -0.0688 0.9827 -0.0902 0.158 Uiso 1 1 d RD . .
O2 O 0.19134(11) 1.2115(5) 0.34952(10) 0.0294(5) Uani 1 1 d . . .
O3 O 0.12533(10) 1.0427(4) 0.17245(10) 0.0213(5) Uani 1 1 d . . .
O4 O 0.22465(10) 1.2115(5) 0.15113(11) 0.0270(5) Uani 1 1 d . . .
O5 O -0.00262(10) 0.8357(4) 0.15569(10) 0.0207(4) Uani 1 1 d . . .
O6 O 0.01540(11) 0.4366(4) 0.20625(10) 0.0232(5) Uani 1 1 d . . .
O7 O -0.15293(13) 0.5641(6) 0.15785(13) 0.0432(7) Uani 1 1 d D . .
H7A H -0.1893(14) 0.660(8) 0.152(2) 0.052 Uiso 1 1 d D . .
O8 O -0.13463(14) 0.7042(6) 0.05905(13) 0.0473(7) Uani 1 1 d . . .
N1 N -0.02755(12) 0.9176(5) 0.28655(12) 0.0167(5) Uani 1 1 d . . .
N2 N -0.18745(12) 0.6301(6) 0.39350(13) 0.0246(6) Uani 1 1 d D . .
H2N H -0.2242(12) 0.683(8) 0.3753(16) 0.029 Uiso 1 1 d D . .
N3 N -0.20954(15) 0.1328(7) 0.55124(14) 0.0308(7) Uani 1 1 d . . .
H3N H -0.214(2) 0.032(8) 0.582(2) 0.037 Uiso 1 1 d . . .
C1 C -0.08845(15) 1.0249(6) 0.28070(15) 0.0208(6) Uani 1 1 d . . .
H1 H -0.0957 1.1666 0.2499 0.025 Uiso 1 1 calc R . .
C2 C -0.14083(15) 0.9391(6) 0.31721(15) 0.0219(6) Uani 1 1 d . . .
H2 H -0.1831 1.0222 0.3118 0.026 Uiso 1 1 calc R . .
C3 C -0.13168(14) 0.7293(6) 0.36231(14) 0.0188(6) Uani 1 1 d . . .
C4 C -0.06790(15) 0.6179(7) 0.36916(15) 0.0234(7) Uani 1 1 d . . .
H4 H -0.0590 0.4752 0.3993 0.028 Uiso 1 1 calc R . .
C5 C -0.01855(15) 0.7215(7) 0.33088(14) 0.0215(6) Uani 1 1 d . . .
H5 H 0.0247 0.6488 0.3363 0.026 Uiso 1 1 calc R . .
C6 C -0.25942(16) 0.1620(8) 0.50927(17) 0.0312(8) Uani 1 1 d . . .
H6 H -0.2999 0.0661 0.5161 0.037 Uiso 1 1 calc R . .
C7 C -0.25224(16) 0.3270(7) 0.45747(15) 0.0276(7) Uani 1 1 d . . .
H7 H -0.2880 0.3490 0.4288 0.033 Uiso 1 1 calc R . .
C8 C -0.19239(16) 0.4651(6) 0.44609(15) 0.0226(7) Uani 1 1 d . . .
C9 C -0.14259(16) 0.4348(8) 0.49157(16) 0.0306(8) Uani 1 1 d . . .
H9 H -0.1019 0.5309 0.4866 0.037 Uiso 1 1 calc R . .
C10 C -0.15261(17) 0.2673(8) 0.54286(16) 0.0340(8) Uani 1 1 d . . .
H10 H -0.1184 0.2461 0.5732 0.041 Uiso 1 1 calc R . .
C11 C 0.15416(14) 1.2065(6) 0.30287(14) 0.0205(6) Uani 1 1 d . . .
C12 C 0.17054(14) 1.3857(6) 0.24427(13) 0.0175(6) Uani 1 1 d . . .
H12 H 0.1321 1.5140 0.2379 0.021 Uiso 1 1 calc R . .
C13 C 0.17405(13) 1.2011(6) 0.18563(14) 0.0180(6) Uani 1 1 d . . .
C14 C 0.23064(15) 1.5731(7) 0.25352(16) 0.0220(6) Uani 1 1 d . . .
H14A H 0.2252 1.6838 0.2922 0.033 Uiso 1 1 calc R . .
H14B H 0.2351 1.6992 0.2172 0.033 Uiso 1 1 calc R . .
H14C H 0.2703 1.4568 0.2571 0.033 Uiso 1 1 calc R . .
C21 C -0.01038(12) 0.5720(6) 0.16261(14) 0.0153(6) Uani 1 1 d . . .
C22 C -0.05294(14) 0.4253(7) 0.11362(15) 0.0207(6) Uani 1 1 d . . .
H22 H -0.0633 0.2334 0.1298 0.025 Uiso 1 1 calc R . .
C23 C -0.11744(15) 0.5813(7) 0.10593(16) 0.0250(7) Uani 1 1 d . . .
C24 C -0.01491(19) 0.3933(9) 0.05221(18) 0.0378(8) Uani 1 1 d . . .
H24A H 0.0259 0.2887 0.0601 0.057 Uiso 1 1 calc R . .
H24B H -0.0041 0.5790 0.0354 0.057 Uiso 1 1 calc R . .
H24C H -0.0420 0.2915 0.0215 0.057 Uiso 1 1 calc R . .

loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_23
_atom_site_aniso_U_13
_atom_site_aniso_U_12
Cu1 0.01164(14) 0.01647(14) 0.01624(14) -0.00060(14) -0.00022(16) -0.00184(13)
O1 0.0166(11) 0.0349(12) 0.0195(11) 0.0022(9) -0.0029(9) -0.0092(9)
O1W 0.127(5) 0.208(7) 0.058(3) 0.038(4) -0.033(3) -0.028(4)
O2 0.0199(11) 0.0483(15) 0.0202(12) -0.0032(10) -0.0039(9) -0.0084(10)
O3 0.0166(10) 0.0252(11) 0.0222(11) -0.0084(9) 0.0022(9) -0.0061(8)
O4 0.0191(10) 0.0368(12) 0.0250(11) -0.0086(10) 0.0071(9) -0.0083(9)
O5 0.0231(11) 0.0164(11) 0.0226(11) 0.0013(9) -0.0028(9) -0.0034(8)
O6 0.0252(11) 0.0188(10) 0.0255(12) 0.0011(8) -0.0065(9) 0.0034(9)
O7 0.0253(13) 0.0615(17) 0.0429(16) 0.0123(14) 0.0027(12) 0.0135(12)
O8 0.0448(16) 0.0617(18) 0.0353(15) 0.0108(14) -0.0093(12) 0.0224(14)
N1 0.0115(11) 0.0199(12) 0.0188(12) 0.0012(10) 0.0004(9) -0.0014(10)
N2 0.0134(12) 0.0377(16) 0.0226(13) 0.0111(12) -0.0023(10) -0.0011(11)
N3 0.0353(17) 0.0357(17) 0.0214(14) 0.0127(13) 0.0032(12) -0.0029(13)
C1 0.0175(15) 0.0211(15) 0.0238(16) 0.0049(12) -0.0019(12) 0.0017(11)
C2 0.0147(14) 0.0244(15) 0.0267(16) 0.0068(12) 0.0030(12) 0.0029(11)
C3 0.0150(13) 0.0260(16) 0.0154(14) 0.0006(12) -0.0015(11) -0.0019(12)
C4 0.0192(15) 0.0275(17) 0.0236(16) 0.0093(13) -0.0022(13) 0.0020(13)
C5 0.0156(14) 0.0266(16) 0.0224(16) 0.0032(13) -0.0002(11) 0.0013(12)
C6 0.0230(16) 0.0383(19) 0.0322(19) 0.0119(15) 0.0017(14) -0.0103(15)
C7 0.0180(14) 0.0391(19) 0.0256(17) 0.0094(13) -0.0005(13) -0.0021(14)
C8 0.0205(15) 0.0269(17) 0.0205(16) 0.0062(12) 0.0013(12) -0.0004(12)
C9 0.0205(16) 0.049(2) 0.0224(17) 0.0101(15) -0.0026(13) -0.0071(15)
C10 0.0245(17) 0.052(2) 0.0258(17) 0.0120(16) -0.0031(14) -0.0033(15)
C11 0.0157(13) 0.0251(15) 0.0208(15) -0.0083(12) 0.0012(12) 0.0018(12)
C12 0.0136(14) 0.0188(14) 0.0201(15) -0.0044(11) -0.0016(10) 0.0001(11)
C13 0.0166(14) 0.0203(14) 0.0171(14) -0.0015(11) -0.0006(11) 0.0026(11)
C14 0.0159(15) 0.0218(14) 0.0281(16) -0.0066(12) -0.0019(13) -0.0051(12)
C21 0.0075(11) 0.0163(13) 0.0221(15) -0.0033(11) 0.0023(11) 0.0008(10)
C22 0.0191(15) 0.0210(15) 0.0221(16) -0.0040(12) 0.0001(12) -0.0041(12)
C23 0.0202(15) 0.0279(17) 0.0269(17) -0.0043(13) -0.0045(13) 0.0015(13)
C24 0.035(2) 0.048(2) 0.031(2) -0.0062(17) 0.0029(15) 0.0059(18)

_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 1.946(2) . ?
Cu1 O3 1.975(2) . ?
Cu1 O5 1.979(2) . ?
Cu1 N1 2.006(2) . ?
Cu1 O6 2.190(2) 1_565 ?
O1 C11 1.269(4) . ?
O1W H1WA 0.95(2) . ?
O1W H1WB 0.9097 . ?
O2 C11 1.241(4) . ?
O3 C13 1.274(3) . ?
O4 C13 1.259(3) . ?
O5 C21 1.277(3) . ?
O6 C21 1.242(4) . ?
O6 Cu1 2.190(2) 1_545 ?
O7 C23 1.315(4) . ?
O7 H7A 0.876(19) . ?
O8 C23 1.203(4) . ?
N1 C5 1.337(4) . ?
N1 C1 1.341(4) . ?
N2 C8 1.366(4) . ?
N2 C3 1.391(4) . ?
N2 H2N 0.875(18) . ?
N3 C10 1.332(4) . ?
N3 C6 1.352(5) . ?
N3 H3N 0.81(5) . ?
C1 C2 1.375(4) . ?
C1 H1 0.9500 . ?
C2 C3 1.395(4) . ?
C2 H2 0.9500 . ?
C3 C4 1.405(4) . ?
C4 C5 1.378(4) . ?
C4 H4 0.9500 . ?
C5 H5 0.9500 . ?
C6 C7 1.357(4) . ?
C6 H6 0.9500 . ?
C7 C8 1.401(4) . ?
C7 H7 0.9500 . ?
C8 C9 1.401(4) . ?
C9 C10 1.362(5) . ?
C9 H9 0.9500 . ?
C10 H10 0.9500 . ?
C11 C12 1.542(4) . ?
C12 C13 1.523(4) . ?
C12 C14 1.523(4) . ?
C12 H12 1.0000 . ?
C14 H14A 0.9800 . ?
C14 H14B 0.9800 . ?
C14 H14C 0.9800 . ?
C21 C22 1.519(4) . ?
C22 C23 1.512(4) . ?
C22 C24 1.518(5) . ?
C22 H22 1.0000 . ?
C24 H24A 0.9800 . ?
C24 H24B 0.9800 . ?
C24 H24C 0.9800 . ?

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 89.49(10) . . ?
O1 Cu1 O5 163.06(9) . . ?
O3 Cu1 O5 90.02(9) . . ?
O1 Cu1 N1 87.21(10) . . ?
O3 Cu1 N1 171.58(10) . . ?
O5 Cu1 N1 90.88(9) . . ?
O1 Cu1 O6 101.72(9) . 1_565 ?
O3 Cu1 O6 92.04(8) . 1_565 ?
O5 Cu1 O6 95.22(8) . 1_565 ?
N1 Cu1 O6 96.22(10) . 1_565 ?
C11 O1 Cu1 125.3(2) . . ?
H1WA O1W H1WB 90.3 . . ?
C13 O3 Cu1 123.43(19) . . ?
C21 O5 Cu1 112.41(18) . . ?
C21 O6 Cu1 139.13(19) . 1_545 ?
C23 O7 H7A 108(3) . . ?
C5 N1 C1 117.2(3) . . ?
C5 N1 Cu1 119.2(2) . . ?
C1 N1 Cu1 123.3(2) . . ?
C8 N2 C3 129.9(3) . . ?
C8 N2 H2N 118(2) . . ?
C3 N2 H2N 112(2) . . ?
C10 N3 C6 120.7(3) . . ?
C10 N3 H3N 119(3) . . ?
C6 N3 H3N 121(3) . . ?
N1 C1 C2 123.0(3) . . ?
N1 C1 H1 118.5 . . ?
C2 C1 H1 118.5 . . ?
C1 C2 C3 119.7(3) . . ?
C1 C2 H2 120.2 . . ?
C3 C2 H2 120.2 . . ?
N2 C3 C2 117.4(3) . . ?
N2 C3 C4 124.7(3) . . ?
C2 C3 C4 117.7(3) . . ?
C5 C4 C3 118.1(3) . . ?
C5 C4 H4 121.0 . . ?
C3 C4 H4 121.0 . . ?
N1 C5 C4 124.3(3) . . ?
N1 C5 H5 117.8 . . ?
C4 C5 H5 117.8 . . ?
N3 C6 C7 120.6(3) . . ?
N3 C6 H6 119.7 . . ?
C7 C6 H6 119.7 . . ?
C6 C7 C8 120.3(3) . . ?
C6 C7 H7 119.8 . . ?
C8 C7 H7 119.8 . . ?
N2 C8 C7 118.3(3) . . ?
N2 C8 C9 124.4(3) . . ?
C7 C8 C9 117.2(3) . . ?
C10 C9 C8 120.0(3) . . ?
C10 C9 H9 120.0 . . ?
C8 C9 H9 120.0 . . ?
N3 C10 C9 121.2(3) . . ?
N3 C10 H10 119.4 . . ?
C9 C10 H10 119.4 . . ?
O2 C11 O1 122.8(3) . . ?
O2 C11 C12 119.8(3) . . ?
O1 C11 C12 117.4(3) . . ?
C13 C12 C14 114.0(2) . . ?
C13 C12 C11 110.1(2) . . ?
C14 C12 C11 113.2(2) . . ?
C13 C12 H12 106.3 . . ?
C14 C12 H12 106.3 . . ?
C11 C12 H12 106.3 . . ?
O4 C13 O3 121.8(3) . . ?
O4 C13 C12 119.1(3) . . ?
O3 C13 C12 119.0(2) . . ?
C12 C14 H14A 109.5 . . ?
C12 C14 H14B 109.5 . . ?
H14A C14 H14B 109.5 . . ?
C12 C14 H14C 109.5 . . ?
H14A C14 H14C 109.5 . . ?
H14B C14 H14C 109.5 . . ?
O6 C21 O5 123.1(3) . . ?
O6 C21 C22 120.4(3) . . ?
O5 C21 C22 116.5(3) . . ?
C23 C22 C24 113.3(3) . . ?
C23 C22 C21 109.7(2) . . ?
C24 C22 C21 110.0(3) . . ?
C23 C22 H22 107.9 . . ?
C24 C22 H22 107.9 . . ?
C21 C22 H22 107.9 . . ?
O8 C23 O7 124.1(3) . . ?
O8 C23 C22 125.4(3) . . ?
O7 C23 C22 110.6(3) . . ?
C22 C24 H24A 109.5 . . ?
C22 C24 H24B 109.5 . . ?
H24A C24 H24B 109.5 . . ?
C22 C24 H24C 109.5 . . ?
H24A C24 H24C 109.5 . . ?
H24B C24 H24C 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
O3 Cu1 O1 C11 31.0(3) . . . . ?
O5 Cu1 O1 C11 119.4(3) . . . . ?
N1 Cu1 O1 C11 -156.8(3) . . . . ?
O6 Cu1 O1 C11 -61.0(3) 1_565 . . . ?
O1 Cu1 O3 C13 -33.5(2) . . . . ?
O5 Cu1 O3 C13 163.5(2) . . . . ?
N1 Cu1 O3 C13 -100.4(7) . . . . ?
O6 Cu1 O3 C13 68.2(2) 1_565 . . . ?
O1 Cu1 O5 C21 17.5(4) . . . . ?
O3 Cu1 O5 C21 105.82(19) . . . . ?
N1 Cu1 O5 C21 -65.8(2) . . . . ?
O6 Cu1 O5 C21 -162.14(19) 1_565 . . . ?
O1 Cu1 N1 C5 -52.7(2) . . . . ?
O3 Cu1 N1 C5 14.4(8) . . . . ?
O5 Cu1 N1 C5 110.5(2) . . . . ?
O6 Cu1 N1 C5 -154.2(2) 1_565 . . . ?
O1 Cu1 N1 C1 134.1(3) . . . . ?
O3 Cu1 N1 C1 -158.8(6) . . . . ?
O5 Cu1 N1 C1 -62.7(2) . . . . ?
O6 Cu1 N1 C1 32.6(2) 1_565 . . . ?
C5 N1 C1 C2 -1.0(5) . . . . ?
Cu1 N1 C1 C2 172.3(2) . . . . ?
N1 C1 C2 C3 -0.6(5) . . . . ?
C8 N2 C3 C2 -167.5(3) . . . . ?
C8 N2 C3 C4 18.0(6) . . . . ?
C1 C2 C3 N2 -173.6(3) . . . . ?
C1 C2 C3 C4 1.2(5) . . . . ?
N2 C3 C4 C5 174.2(3) . . . . ?
C2 C3 C4 C5 -0.3(5) . . . . ?
C1 N1 C5 C4 2.1(5) . . . . ?
Cu1 N1 C5 C4 -171.5(3) . . . . ?
C3 C4 C5 N1 -1.5(5) . . . . ?
C10 N3 C6 C7 0.6(6) . . . . ?
N3 C6 C7 C8 1.3(5) . . . . ?
C3 N2 C8 C7 -161.4(3) . . . . ?
C3 N2 C8 C9 22.0(6) . . . . ?
C6 C7 C8 N2 -179.7(3) . . . . ?
C6 C7 C8 C9 -2.9(5) . . . . ?
N2 C8 C9 C10 179.2(3) . . . . ?
C7 C8 C9 C10 2.6(5) . . . . ?
C6 N3 C10 C9 -0.9(6) . . . . ?
C8 C9 C10 N3 -0.8(6) . . . . ?
Cu1 O1 C11 O2 -172.6(2) . . . . ?
Cu1 O1 C11 C12 8.0(4) . . . . ?
O2 C11 C12 C13 124.3(3) . . . . ?
O1 C11 C12 C13 -56.3(3) . . . . ?
O2 C11 C12 C14 -4.6(4) . . . . ?
O1 C11 C12 C14 174.8(3) . . . . ?
Cu1 O3 C13 O4 177.4(2) . . . . ?
Cu1 O3 C13 C12 -3.5(4) . . . . ?
C14 C12 C13 O4 1.3(4) . . . . ?
C11 C12 C13 O4 -127.2(3) . . . . ?
C14 C12 C13 O3 -177.8(3) . . . . ?
C11 C12 C13 O3 53.7(3) . . . . ?
Cu1 O6 C21 O5 -155.2(2) 1_545 . . . ?
Cu1 O6 C21 C22 24.1(4) 1_545 . . . ?
Cu1 O5 C21 O6 -6.2(3) . . . . ?
Cu1 O5 C21 C22 174.51(18) . . . . ?
O6 C21 C22 C23 130.6(3) . . . . ?
O5 C21 C22 C23 -50.0(3) . . . . ?
O6 C21 C22 C24 -104.1(3) . . . . ?
O5 C21 C22 C24 75.3(3) . . . . ?
C24 C22 C23 O8 -9.8(5) . . . . ?
C21 C22 C23 O8 113.5(4) . . . . ?
C24 C22 C23 O7 170.0(3) . . . . ?
C21 C22 C23 O7 -66.7(4) . . . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
O1W H1WA O8 0.95(2) 2.36(2) 3.143(6) 139.1(18) .
O1W H1WB O1 0.91 2.40 3.001(5) 123.2 2_574
N2 H2N O2 0.875(18) 1.86(2) 2.732(3) 171(4) 3_475
N3 H3N O4 0.81(5) 1.88(5) 2.694(4) 178(5) 2_565
O7 H7A O4 0.876(19) 1.85(2) 2.705(3) 165(4) 3_475

_diffrn_measured_fraction_theta_max 0.959
_diffrn_reflns_theta_full        25.00
_diffrn_measured_fraction_theta_full 1.000
_refine_diff_density_max         0.513
_refine_diff_density_min         -0.417
_refine_diff_density_rms         0.069


# Attachment '0cudmmaldpafinal.cif'

data_c2c
_database_code_depnum_ccdc_archive 'CCDC 735596'

_audit_update_record             
;
2009-06-09 # Formatted by publCIF
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C40 H43 Cl2 Cu3 N9 O18'
_chemical_formula_weight         1199.36

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cu Cu 0.3201 1.2651 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_H-M   C2/c

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

_cell_length_a                   29.090(4)
_cell_length_b                   9.1837(11)
_cell_length_c                   21.114(3)
_cell_angle_alpha                90.00
_cell_angle_beta                 127.7640(10)
_cell_angle_gamma                90.00
_cell_volume                     4459.1(10)
_cell_formula_units_Z            4
_cell_measurement_temperature    173(2)
_cell_measurement_reflns_used    ?
_cell_measurement_theta_min      ?
_cell_measurement_theta_max      ?

_exptl_crystal_description       block
_exptl_crystal_colour            blue
_exptl_crystal_size_max          0.60
_exptl_crystal_size_mid          0.35
_exptl_crystal_size_min          0.35
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.781
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             2428
_exptl_absorpt_coefficient_mu    1.627
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.6590
_exptl_absorpt_correction_T_max  0.7457
_exptl_absorpt_process_details   SADABS

_exptl_special_details           
;
?
;

_diffrn_ambient_temperature      173(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  ?
_diffrn_measurement_method       ?
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            24094
_diffrn_reflns_av_R_equivalents  0.0367
_diffrn_reflns_av_sigmaI/netI    0.0328
_diffrn_reflns_limit_h_min       -36
_diffrn_reflns_limit_h_max       38
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_l_min       -27
_diffrn_reflns_limit_l_max       27
_diffrn_reflns_theta_min         1.77
_diffrn_reflns_theta_max         28.26
_reflns_number_total             5143
_reflns_number_gt                4206
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    ?
_computing_publication_material  ?

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

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[\s^2^(Fo^2^)+(0.0462P)^2^+16.5218P] where P=(Fo^2^+2Fc^2^)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         5143
_refine_ls_number_parameters     367
_refine_ls_number_restraints     2
_refine_ls_R_factor_all          0.0531
_refine_ls_R_factor_gt           0.0396
_refine_ls_wR_factor_ref         0.1025
_refine_ls_wR_factor_gt          0.0961
_refine_ls_goodness_of_fit_ref   1.087
_refine_ls_restrained_S_all      1.087
_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 0.250188(14) -0.21747(4) 0.28985(2) 0.01180(10) Uani 1 1 d . . .
Cu2 Cu 0.2500 -0.2500 0.5000 0.01128(12) Uani 1 2 d S . .
C1 C -0.12349(14) -0.2353(4) -0.0857(2) 0.0251(7) Uani 1 1 d . . .
H1 H -0.1314 -0.1447 -0.1101 0.030 Uiso 1 1 calc R . .
C2 C -0.06698(14) -0.2644(4) -0.0201(2) 0.0266(7) Uani 1 1 d . . .
H2 H -0.0380 -0.1948 -0.0009 0.032 Uiso 1 1 calc R . .
C3 C -0.05410(12) -0.4003(3) 0.01684(17) 0.0165(6) Uani 1 1 d . . .
C4 C -0.10060(12) -0.4967(3) -0.01357(17) 0.0168(6) Uani 1 1 d . . .
H4 H -0.0944 -0.5871 0.0104 0.020 Uiso 1 1 calc R . .
C5 C -0.15502(12) -0.4573(3) -0.07857(17) 0.0167(6) Uani 1 1 d . . .
H5 H -0.1852 -0.5231 -0.0978 0.020 Uiso 1 1 calc R . .
C8 C 0.05526(12) -0.3949(3) 0.12231(17) 0.0152(6) Uani 1 1 d . . .
C7 C 0.07056(13) -0.2700(3) 0.1020(2) 0.0244(7) Uani 1 1 d . . .
H7 H 0.0423 -0.2144 0.0579 0.029 Uiso 1 1 calc R . .
C9 C 0.10062(13) -0.4759(3) 0.18794(18) 0.0193(6) Uani 1 1 d . . .
H9 H 0.0926 -0.5629 0.2019 0.023 Uiso 1 1 calc R . .
C6 C 0.12821(14) -0.2295(3) 0.14792(19) 0.0229(7) Uani 1 1 d . . .
H6 H 0.1379 -0.1465 0.1332 0.028 Uiso 1 1 calc R . .
C11 C 0.34346(12) -0.0346(3) 0.59363(17) 0.0157(6) Uani 1 1 d . . .
H11 H 0.3120 0.0289 0.5682 0.019 Uiso 1 1 calc R . .
C12 C 0.39807(13) 0.0212(3) 0.65109(17) 0.0170(6) Uani 1 1 d . . .
H12 H 0.4029 0.1200 0.6631 0.020 Uiso 1 1 calc R . .
C13 C 0.44632(12) -0.0721(3) 0.69129(17) 0.0154(6) Uani 1 1 d . . .
C14 C 0.43638(13) -0.2174(3) 0.66673(18) 0.0174(6) Uani 1 1 d . . .
H14 H 0.4672 -0.2825 0.6894 0.021 Uiso 1 1 calc R . .
C15 C 0.37995(13) -0.2631(3) 0.60807(18) 0.0175(6) Uani 1 1 d . . .
H15 H 0.3741 -0.3603 0.5925 0.021 Uiso 1 1 calc R . .
C10 C 0.15647(13) -0.4265(3) 0.23107(18) 0.0189(6) Uani 1 1 d . . .
H10 H 0.1857 -0.4804 0.2751 0.023 Uiso 1 1 calc R . .
C51 C 0.21803(11) -0.0630(3) 0.38242(16) 0.0114(5) Uani 1 1 d . . .
C52 C 0.19441(12) 0.0769(3) 0.33197(17) 0.0144(6) Uani 1 1 d . . .
C53 C 0.21667(11) 0.1060(3) 0.28258(16) 0.0128(5) Uani 1 1 d . . .
C54 C 0.20642(19) 0.2068(3) 0.3852(2) 0.0310(8) Uani 1 1 d . . .
H54A H 0.1915 0.2938 0.3533 0.046 Uiso 1 1 calc R . .
H54B H 0.2476 0.2165 0.4262 0.046 Uiso 1 1 calc R . .
H54C H 0.1877 0.1919 0.4095 0.046 Uiso 1 1 calc R . .
C55 C 0.12753(13) 0.0531(4) 0.2695(2) 0.0268(7) Uani 1 1 d . . .
H55A H 0.1101 0.1375 0.2359 0.040 Uiso 1 1 calc R . .
H55B H 0.1112 0.0376 0.2970 0.040 Uiso 1 1 calc R . .
H55C H 0.1201 -0.0305 0.2372 0.040 Uiso 1 1 calc R . .
O1W O 0.2929(3) 0.4956(7) 0.4142(4) 0.138(2) Uani 1 1 d . . .
O1 O 0.22686(9) 0.2391(2) 0.27825(12) 0.0162(4) Uani 1 1 d . . .
O4 O 0.22954(8) -0.1778(2) 0.36231(12) 0.0146(4) Uani 1 1 d . . .
O3 O 0.22313(8) -0.0600(2) 0.44660(11) 0.0141(4) Uani 1 1 d . . .
O2 O 0.22074(9) 0.0063(2) 0.24648(12) 0.0154(4) Uani 1 1 d . . .
N1 N -0.16759(10) -0.3286(3) -0.11648(14) 0.0152(5) Uani 1 1 d . . .
N2 N -0.00010(11) -0.4512(3) 0.08190(16) 0.0209(5) Uani 1 1 d D . .
H2N H -0.0015(15) -0.538(3) 0.098(2) 0.025 Uiso 1 1 d D . .
N4 N 0.33304(10) -0.1761(3) 0.57211(14) 0.0139(5) Uani 1 1 d . . .
N5 N 0.5000 -0.0105(4) 0.7500 0.0185(7) Uani 1 2 d SD . .
H5N H 0.5000 0.085(2) 0.7500 0.022 Uiso 1 2 d SD . .
N3 N 0.17114(10) -0.3033(3) 0.21270(14) 0.0149(5) Uani 1 1 d . . .
Cl1 Cl 0.03492(4) 0.12941(9) 0.39273(5) 0.0303(2) Uani 1 1 d . . .
O5A O 0.0071(4) 0.2687(10) 0.3547(4) 0.0312(15) Uani 0.70 1 d P A 1
O6A O 0.0240(4) 0.0305(7) 0.3358(4) 0.066(2) Uani 0.70 1 d P A 1
O7A O 0.0103(3) 0.0753(7) 0.4302(4) 0.0633(16) Uani 0.70 1 d P A 1
O8A O 0.0942(3) 0.1554(8) 0.4544(4) 0.070(2) Uani 0.70 1 d P A 1
O5B O 0.0931(8) 0.1352(19) 0.4126(17) 0.113(10) Uani 0.30 1 d P A 2
O6B O 0.0064(7) -0.0014(15) 0.3530(12) 0.074(6) Uani 0.30 1 d P A 2
O7B O 0.0016(14) 0.251(3) 0.358(2) 0.100(12) Uani 0.30 1 d P A 2
O8B O 0.0485(13) 0.115(3) 0.4670(10) 0.129(10) Uani 0.30 1 d P A 2

loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_23
_atom_site_aniso_U_13
_atom_site_aniso_U_12
Cu1 0.00801(17) 0.01250(17) 0.01262(17) -0.00240(12) 0.00516(14) -0.00037(12)
Cu2 0.0111(2) 0.0095(2) 0.0105(2) 0.00178(17) 0.0052(2) 0.00078(17)
C1 0.0181(16) 0.0230(16) 0.0261(17) 0.0075(13) 0.0094(14) 0.0003(12)
C2 0.0140(15) 0.0223(16) 0.0305(18) 0.0061(13) 0.0070(14) -0.0035(12)
C3 0.0097(13) 0.0228(15) 0.0139(14) 0.0000(11) 0.0056(12) -0.0007(11)
C4 0.0139(14) 0.0178(14) 0.0159(14) 0.0026(11) 0.0076(12) 0.0004(11)
C5 0.0115(14) 0.0189(14) 0.0182(14) -0.0011(11) 0.0084(12) -0.0022(11)
C8 0.0074(13) 0.0202(14) 0.0129(13) -0.0033(11) 0.0037(11) -0.0009(10)
C7 0.0139(15) 0.0219(16) 0.0236(16) 0.0064(13) 0.0045(14) 0.0008(12)
C9 0.0176(15) 0.0191(15) 0.0188(15) 0.0036(12) 0.0100(13) -0.0019(11)
C6 0.0175(15) 0.0179(15) 0.0240(16) 0.0039(12) 0.0079(14) -0.0012(12)
C11 0.0150(14) 0.0154(14) 0.0150(14) 0.0014(11) 0.0082(12) 0.0038(11)
C12 0.0187(15) 0.0117(13) 0.0172(14) -0.0003(11) 0.0093(13) 0.0009(11)
C13 0.0122(13) 0.0184(14) 0.0128(13) 0.0016(11) 0.0063(12) 0.0006(11)
C14 0.0155(14) 0.0147(14) 0.0206(15) 0.0002(11) 0.0103(13) 0.0031(11)
C15 0.0170(14) 0.0128(13) 0.0220(15) -0.0024(11) 0.0115(13) 0.0001(11)
C10 0.0133(14) 0.0215(15) 0.0153(14) 0.0023(11) 0.0054(12) -0.0007(11)
C51 0.0055(12) 0.0127(13) 0.0121(13) 0.0018(10) 0.0034(11) -0.0012(9)
C52 0.0160(14) 0.0138(13) 0.0166(14) 0.0046(11) 0.0116(12) 0.0045(10)
C53 0.0050(12) 0.0180(14) 0.0112(13) 0.0032(10) 0.0028(11) 0.0020(10)
C54 0.062(3) 0.0146(15) 0.036(2) 0.0060(13) 0.040(2) 0.0098(15)
C55 0.0138(15) 0.0380(19) 0.0296(18) 0.0180(15) 0.0139(14) 0.0114(13)
O1W 0.147(6) 0.125(5) 0.142(5) -0.005(4) 0.088(5) -0.017(4)
O1 0.0185(10) 0.0121(10) 0.0214(11) 0.0035(8) 0.0139(9) 0.0005(8)
O4 0.0160(10) 0.0129(10) 0.0165(10) 0.0023(8) 0.0108(9) 0.0019(8)
O3 0.0135(10) 0.0155(10) 0.0110(9) 0.0029(7) 0.0064(8) 0.0028(8)
O2 0.0155(10) 0.0165(10) 0.0158(10) 0.0006(8) 0.0103(9) 0.0009(8)
N1 0.0106(11) 0.0189(12) 0.0148(12) 0.0002(9) 0.0071(10) -0.0007(9)
N2 0.0116(12) 0.0221(13) 0.0196(13) 0.0043(10) 0.0047(11) -0.0014(10)
N4 0.0138(12) 0.0147(12) 0.0139(11) 0.0013(9) 0.0089(10) 0.0008(9)
N5 0.0141(17) 0.0114(16) 0.0215(18) 0.000 0.0066(16) 0.000
N3 0.0116(11) 0.0145(12) 0.0163(12) -0.0014(9) 0.0073(10) -0.0017(9)
Cl1 0.0333(5) 0.0194(4) 0.0323(4) -0.0044(3) 0.0170(4) 0.0028(3)
O5A 0.035(4) 0.016(3) 0.037(3) 0.003(2) 0.019(3) 0.005(2)
O6A 0.101(6) 0.044(4) 0.046(3) -0.007(3) 0.040(4) 0.030(4)
O7A 0.090(5) 0.055(3) 0.059(4) 0.006(3) 0.053(4) 0.000(3)
O8A 0.028(3) 0.056(3) 0.081(5) -0.009(3) 0.010(3) 0.011(3)
O5B 0.083(12) 0.050(10) 0.27(3) 0.044(14) 0.144(19) 0.027(8)
O6B 0.053(8) 0.015(6) 0.108(15) -0.023(7) 0.026(9) -0.006(5)
O7B 0.048(12) 0.015(8) 0.17(2) -0.008(11) 0.034(14) -0.001(7)
O8B 0.21(3) 0.115(17) 0.045(10) -0.001(10) 0.070(14) 0.027(18)

_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 1.962(2) 4_545 ?
Cu1 O4 1.9900(19) . ?
Cu1 N3 1.993(2) . ?
Cu1 N1 2.004(2) 8_546 ?
Cu1 O2 2.199(2) . ?
Cu2 O3 1.9617(19) 7_546 ?
Cu2 O3 1.9617(19) . ?
Cu2 N4 2.027(2) . ?
Cu2 N4 2.027(2) 7_546 ?
C1 N1 1.334(4) . ?
C1 C2 1.379(4) . ?
C2 C3 1.396(4) . ?
C3 N2 1.389(4) . ?
C3 C4 1.401(4) . ?
C4 C5 1.364(4) . ?
C5 N1 1.346(4) . ?
C8 N2 1.380(4) . ?
C8 C7 1.390(4) . ?
C8 C9 1.405(4) . ?
C7 C6 1.378(4) . ?
C9 C10 1.364(4) . ?
C6 N3 1.340(4) . ?
C11 N4 1.348(4) . ?
C11 C12 1.377(4) . ?
C12 C13 1.402(4) . ?
C13 N5 1.387(3) . ?
C13 C14 1.396(4) . ?
C14 C15 1.384(4) . ?
C15 N4 1.345(4) . ?
C10 N3 1.348(4) . ?
C51 O4 1.256(3) . ?
C51 O3 1.270(3) . ?
C51 C52 1.537(4) . ?
C52 C54 1.525(4) . ?
C52 C53 1.551(4) . ?
C52 C55 1.559(4) . ?
C53 O2 1.243(3) . ?
C53 O1 1.274(3) . ?
O1 Cu1 1.961(2) 4 ?
N1 Cu1 2.004(2) 8_445 ?
N5 C13 1.387(3) 2_656 ?
Cl1 O7B 1.36(3) . ?
Cl1 O8B 1.370(17) . ?
Cl1 O6A 1.380(6) . ?
Cl1 O8A 1.406(6) . ?
Cl1 O6B 1.409(13) . ?
Cl1 O7A 1.443(6) . ?
Cl1 O5A 1.463(9) . ?
Cl1 O5B 1.473(14) . ?

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 177.79(8) 4_545 . ?
O1 Cu1 N3 93.48(9) 4_545 . ?
O4 Cu1 N3 87.73(9) . . ?
O1 Cu1 N1 91.72(9) 4_545 8_546 ?
O4 Cu1 N1 86.70(9) . 8_546 ?
N3 Cu1 N1 166.41(10) . 8_546 ?
O1 Cu1 O2 96.06(8) 4_545 . ?
O4 Cu1 O2 85.69(8) . . ?
N3 Cu1 O2 93.95(9) . . ?
N1 Cu1 O2 97.98(9) 8_546 . ?
O3 Cu2 O3 180.0 7_546 . ?
O3 Cu2 N4 89.68(9) 7_546 . ?
O3 Cu2 N4 90.33(9) . . ?
O3 Cu2 N4 90.32(9) 7_546 7_546 ?
O3 Cu2 N4 89.67(9) . 7_546 ?
N4 Cu2 N4 179.997(1) . 7_546 ?
N1 C1 C2 124.3(3) . . ?
C1 C2 C3 118.7(3) . . ?
N2 C3 C2 127.4(3) . . ?
N2 C3 C4 115.5(3) . . ?
C2 C3 C4 117.1(3) . . ?
C5 C4 C3 119.5(3) . . ?
N1 C5 C4 123.8(3) . . ?
N2 C8 C7 126.2(3) . . ?
N2 C8 C9 116.5(3) . . ?
C7 C8 C9 117.2(3) . . ?
C6 C7 C8 119.1(3) . . ?
C10 C9 C8 119.8(3) . . ?
N3 C6 C7 123.7(3) . . ?
N4 C11 C12 123.7(3) . . ?
C11 C12 C13 119.5(3) . . ?
N5 C13 C14 125.9(3) . . ?
N5 C13 C12 116.9(3) . . ?
C14 C13 C12 117.2(3) . . ?
C15 C14 C13 119.0(3) . . ?
N4 C15 C14 124.2(3) . . ?
N3 C10 C9 123.0(3) . . ?
O4 C51 O3 119.9(2) . . ?
O4 C51 C52 124.5(2) . . ?
O3 C51 C52 115.6(2) . . ?
C54 C52 C51 109.9(2) . . ?
C54 C52 C53 111.0(2) . . ?
C51 C52 C53 114.6(2) . . ?
C54 C52 C55 109.7(3) . . ?
C51 C52 C55 105.4(2) . . ?
C53 C52 C55 105.9(2) . . ?
O2 C53 O1 123.3(3) . . ?
O2 C53 C52 121.4(2) . . ?
O1 C53 C52 115.2(2) . . ?
C53 O1 Cu1 116.51(18) . 4 ?
C51 O4 Cu1 133.01(18) . . ?
C51 O3 Cu2 109.80(17) . . ?
C53 O2 Cu1 126.34(18) . . ?
C1 N1 C5 116.4(3) . . ?
C1 N1 Cu1 123.7(2) . 8_445 ?
C5 N1 Cu1 119.83(19) . 8_445 ?
C8 N2 C3 132.1(3) . . ?
C15 N4 C11 116.2(2) . . ?
C15 N4 Cu2 123.7(2) . . ?
C11 N4 Cu2 119.64(19) . . ?
C13 N5 C13 131.8(4) . 2_656 ?
C6 N3 C10 117.2(3) . . ?
C6 N3 Cu1 121.5(2) . . ?
C10 N3 Cu1 120.5(2) . . ?
O7B Cl1 O8B 107.7(17) . . ?
O7B Cl1 O6A 111.5(14) . . ?
O8B Cl1 O6A 133.1(10) . . ?
O7B Cl1 O8A 115.1(14) . . ?
O8B Cl1 O8A 68.1(13) . . ?
O6A Cl1 O8A 114.6(4) . . ?
O7B Cl1 O6B 114.5(15) . . ?
O8B Cl1 O6B 104.3(14) . . ?
O6A Cl1 O6B 35.2(7) . . ?
O8A Cl1 O6B 129.7(7) . . ?
O7B Cl1 O7A 98.2(14) . . ?
O8B Cl1 O7A 39.5(12) . . ?
O6A Cl1 O7A 109.0(4) . . ?
O8A Cl1 O7A 106.8(4) . . ?
O6B Cl1 O7A 73.9(8) . . ?
O7B Cl1 O5A 10.3(17) . . ?
O8B Cl1 O5A 113.0(10) . . ?
O6A Cl1 O5A 110.0(4) . . ?
O8A Cl1 O5A 108.2(5) . . ?
O6B Cl1 O5A 119.5(8) . . ?
O7A Cl1 O5A 108.0(4) . . ?
O7B Cl1 O5B 116.2(15) . . ?
O8B Cl1 O5B 101.7(16) . . ?
O6A Cl1 O5B 83.3(10) . . ?
O8A Cl1 O5B 35.6(10) . . ?
O6B Cl1 O5B 110.9(11) . . ?
O7A Cl1 O5B 136.5(10) . . ?
O5A Cl1 O5B 106.1(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
N1 C1 C2 C3 0.6(6) . . . . ?
C1 C2 C3 N2 178.5(3) . . . . ?
C1 C2 C3 C4 -2.7(5) . . . . ?
N2 C3 C4 C5 -178.5(3) . . . . ?
C2 C3 C4 C5 2.5(4) . . . . ?
C3 C4 C5 N1 -0.2(5) . . . . ?
N2 C8 C7 C6 -178.9(3) . . . . ?
C9 C8 C7 C6 -2.1(5) . . . . ?
N2 C8 C9 C10 -179.6(3) . . . . ?
C7 C8 C9 C10 3.4(4) . . . . ?
C8 C7 C6 N3 -0.9(5) . . . . ?
N4 C11 C12 C13 -0.9(4) . . . . ?
C11 C12 C13 N5 -178.4(2) . . . . ?
C11 C12 C13 C14 3.9(4) . . . . ?
N5 C13 C14 C15 178.9(2) . . . . ?
C12 C13 C14 C15 -3.5(4) . . . . ?
C13 C14 C15 N4 0.2(5) . . . . ?
C8 C9 C10 N3 -1.7(5) . . . . ?
O4 C51 C52 C54 -159.2(3) . . . . ?
O3 C51 C52 C54 24.1(3) . . . . ?
O4 C51 C52 C53 -33.4(4) . . . . ?
O3 C51 C52 C53 149.9(2) . . . . ?
O4 C51 C52 C55 82.7(3) . . . . ?
O3 C51 C52 C55 -94.0(3) . . . . ?
C54 C52 C53 O2 167.0(3) . . . . ?
C51 C52 C53 O2 41.8(4) . . . . ?
C55 C52 C53 O2 -74.0(3) . . . . ?
C54 C52 C53 O1 -16.9(3) . . . . ?
C51 C52 C53 O1 -142.2(2) . . . . ?
C55 C52 C53 O1 102.1(3) . . . . ?
O2 C53 O1 Cu1 0.1(3) . . . 4 ?
C52 C53 O1 Cu1 -175.82(17) . . . 4 ?
O3 C51 O4 Cu1 -158.91(19) . . . . ?
C52 C51 O4 Cu1 24.5(4) . . . . ?
O1 Cu1 O4 C51 129(2) 4_545 . . . ?
N3 Cu1 O4 C51 -107.7(3) . . . . ?
N1 Cu1 O4 C51 84.7(3) 8_546 . . . ?
O2 Cu1 O4 C51 -13.6(2) . . . . ?
O4 C51 O3 Cu2 0.3(3) . . . . ?
C52 C51 O3 Cu2 177.19(17) . . . . ?
O3 Cu2 O3 C51 -152(4) 7_546 . . . ?
N4 Cu2 O3 C51 96.94(18) . . . . ?
N4 Cu2 O3 C51 -83.06(18) 7_546 . . . ?
O1 C53 O2 Cu1 145.2(2) . . . . ?
C52 C53 O2 Cu1 -39.1(3) . . . . ?
O1 Cu1 O2 C53 -157.5(2) 4_545 . . . ?
O4 Cu1 O2 C53 21.2(2) . . . . ?
N3 Cu1 O2 C53 108.6(2) . . . . ?
N1 Cu1 O2 C53 -64.9(2) 8_546 . . . ?
C2 C1 N1 C5 1.7(5) . . . . ?
C2 C1 N1 Cu1 178.4(3) . . . 8_445 ?
C4 C5 N1 C1 -1.9(4) . . . . ?
C4 C5 N1 Cu1 -178.8(2) . . . 8_445 ?
C7 C8 N2 C3 -4.7(5) . . . . ?
C9 C8 N2 C3 178.6(3) . . . . ?
C2 C3 N2 C8 -8.1(6) . . . . ?
C4 C3 N2 C8 173.0(3) . . . . ?
C14 C15 N4 C11 2.8(4) . . . . ?
C14 C15 N4 Cu2 -169.6(2) . . . . ?
C12 C11 N4 C15 -2.5(4) . . . . ?
C12 C11 N4 Cu2 170.3(2) . . . . ?
O3 Cu2 N4 C15 24.0(2) 7_546 . . . ?
O3 Cu2 N4 C15 -156.0(2) . . . . ?
N4 Cu2 N4 C15 120(4) 7_546 . . . ?
O3 Cu2 N4 C11 -148.1(2) 7_546 . . . ?
O3 Cu2 N4 C11 31.9(2) . . . . ?
N4 Cu2 N4 C11 -52(4) 7_546 . . . ?
C14 C13 N5 C13 -14.4(2) . . . 2_656 ?
C12 C13 N5 C13 168.1(3) . . . 2_656 ?
C7 C6 N3 C10 2.6(5) . . . . ?
C7 C6 N3 Cu1 -166.4(3) . . . . ?
C9 C10 N3 C6 -1.3(4) . . . . ?
C9 C10 N3 Cu1 167.8(2) . . . . ?
O1 Cu1 N3 C6 -79.6(2) 4_545 . . . ?
O4 Cu1 N3 C6 102.3(2) . . . . ?
N1 Cu1 N3 C6 168.1(4) 8_546 . . . ?
O2 Cu1 N3 C6 16.8(2) . . . . ?
O1 Cu1 N3 C10 111.8(2) 4_545 . . . ?
O4 Cu1 N3 C10 -66.4(2) . . . . ?
N1 Cu1 N3 C10 -0.5(6) 8_546 . . . ?
O2 Cu1 N3 C10 -151.9(2) . . . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
N2 H2N O5A 0.876(18) 2.09(2) 2.964(9) 173(3) 2_545
N2 H2N O7B 0.876(18) 2.15(4) 3.02(3) 178(4) 2_545
N5 H5N O5A 0.88(2) 2.484(13) 3.049(9) 122.7(4) 8_556
N5 H5N O5A 0.88(2) 2.484(13) 3.049(9) 122.7(4) 7_556

_diffrn_measured_fraction_theta_max 0.931
_diffrn_reflns_theta_full        25.00
_diffrn_measured_fraction_theta_full 0.999
_refine_diff_density_max         0.837
_refine_diff_density_min         -0.767
_refine_diff_density_rms         0.100