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

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

data_Compound1
_database_code_depnum_ccdc_archive 'CCDC 1414611'
_audit_update_record             
;
2015-09-17 deposited with the CCDC.
2015-09-28 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C34 H22 N4 O10 Zn2, 2(C3 H7 N O)'
_chemical_formula_sum            'C40 H36 N6 O12 Zn2'
_chemical_formula_weight         923.49

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'
Zn Zn 0.2839 1.4301 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      monoclinic
_space_group_IT_number           4
_space_group_name_H-M_alt        'P 21'
_space_group_name_Hall           'P 2yb'

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

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

_cell_length_a                   8.0350(9)
_cell_length_b                   24.892(3)
_cell_length_c                   10.8856(13)
_cell_angle_alpha                90
_cell_angle_beta                 111.560(4)
_cell_angle_gamma                90
_cell_volume                     2024.9(4)
_cell_formula_units_Z            2
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    9524
_cell_measurement_theta_min      2.59
_cell_measurement_theta_max      25.37

_exptl_crystal_description       block
_exptl_crystal_colour            white
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.515
_exptl_crystal_F_000             948
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.320
_exptl_crystal_size_mid          0.190
_exptl_crystal_size_min          0.110
_exptl_absorpt_coefficient_mu    1.255
_shelx_estimated_absorpt_T_min   0.689
_shelx_estimated_absorpt_T_max   0.874
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.750
_exptl_absorpt_correction_T_max  0.852
_exptl_absorpt_process_details   sadabs
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      296(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruker APEX-II PHOTON 100'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            46996
_diffrn_reflns_av_unetI/netI     0.0140
_diffrn_reflns_av_R_equivalents  0.0219
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_k_min       -30
_diffrn_reflns_limit_k_max       30
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_theta_min         2.012
_diffrn_reflns_theta_max         25.372
_diffrn_reflns_theta_full        25.000
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measured_fraction_theta_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_point_group_measured_fraction_full 0.999
_reflns_number_total             7404
_reflns_number_gt                7306
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.952
_reflns_Friedel_fraction_max     0.998
_reflns_Friedel_fraction_full    0.999

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

_computing_data_collection       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SIR97 (Giacovazzo et al, 1999)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    'Mercury CSD 3.5.1, 2008'
_computing_publication_material  'WinGX publication routines (Farrugia, 1999)'
_refine_special_details          
;
 Refined as a 2-component inversion twin.
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0542P)²+0.6282P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_abs_structure_details 
;
 Refined as an inversion twin.
;
_refine_ls_abs_structure_Flack   0.499(15)
_chemical_absolute_configuration unk
_refine_ls_number_reflns         7404
_refine_ls_number_parameters     552
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0322
_refine_ls_R_factor_gt           0.0318
_refine_ls_wR_factor_ref         0.0801
_refine_ls_wR_factor_gt          0.0795
_refine_ls_goodness_of_fit_ref   1.109
_refine_ls_restrained_S_all      1.109
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
C2 C 0.7205(12) 0.1524(3) 0.0933(11) 0.097(3) Uani 1 1 d . . . . .
H2 H 0.7633 0.1211 0.0685 0.116 Uiso 1 1 calc R U . . .
C4 C 0.2592(6) 0.50140(18) 0.0312(4) 0.0353(10) Uani 1 1 d . . . . .
C5 C 0.1286(6) 0.50059(19) -0.1084(4) 0.0361(10) Uani 1 1 d . . . . .
C6 C -0.1400(6) 0.5328(3) -0.2779(4) 0.0500(12) Uani 1 1 d . . . . .
H6 H -0.2417 0.5543 -0.3029 0.060 Uiso 1 1 calc R U . . .
C7 C -0.1048(6) 0.50202(19) -0.3723(4) 0.0357(10) Uani 1 1 d . . . . .
C8 C -0.2360(6) 0.50061(18) -0.5127(4) 0.0338(9) Uani 1 1 d . . . . .
C9 C 0.0492(6) 0.4711(3) -0.3333(4) 0.0468(11) Uani 1 1 d . . . . .
H9 H 0.0749 0.4506 -0.3956 0.056 Uiso 1 1 calc R U . . .
C10 C 0.1647(6) 0.4701(3) -0.2033(4) 0.0490(11) Uani 1 1 d . . . . .
H10 H 0.2675 0.4491 -0.1787 0.059 Uiso 1 1 calc R U . . .
C11 C 0.3359(8) 0.6396(2) 0.3959(7) 0.0561(15) Uani 1 1 d . . . . .
H11 H 0.4361 0.6463 0.3748 0.067 Uiso 1 1 calc R U . . .
C12 C 0.2605(8) 0.6813(2) 0.4382(7) 0.0578(15) Uani 1 1 d . . . . .
H12 H 0.3078 0.7157 0.4435 0.069 Uiso 1 1 calc R U . . .
C13 C 0.1132(6) 0.6724(2) 0.4735(5) 0.0381(10) Uani 1 1 d . . . . .
C14 C -0.0930(8) 0.7168(2) 0.5643(6) 0.0523(14) Uani 1 1 d . . . . .
C15 C 0.1480(8) 0.2712(2) 0.4057(6) 0.0445(12) Uani 1 1 d . . . . .
C18 C 0.2854(6) 0.3676(2) 0.3533(5) 0.0338(10) Uani 1 1 d . . . . .
C19 C 0.1481(7) 0.3680(2) 0.3995(5) 0.0393(11) Uani 1 1 d . . . . .
H19 H 0.1004 0.4004 0.4134 0.047 Uiso 1 1 calc R U . . .
C20 C 0.0799(8) 0.3196(3) 0.4259(6) 0.0492(13) Uani 1 1 d . . . . .
H20 H -0.0129 0.3201 0.4576 0.059 Uiso 1 1 calc R U . . .
C21 C 0.2846(8) 0.2718(2) 0.3553(7) 0.0539(14) Uani 1 1 d . . . . .
H21 H 0.3307 0.2395 0.3388 0.065 Uiso 1 1 calc R U . . .
C22 C 0.3509(8) 0.3185(3) 0.3300(6) 0.0525(14) Uani 1 1 d . . . . .
H22 H 0.4420 0.3178 0.2965 0.063 Uiso 1 1 calc R U . . .
C23 C 0.9650(8) 0.3826(3) 0.0448(6) 0.0508(14) Uani 1 1 d . . . . .
H23 H 1.0591 0.3908 0.0175 0.061 Uiso 1 1 calc R U . . .
C24 C 0.8961(7) 0.3307(2) 0.0354(5) 0.0475(12) Uani 1 1 d . . . . .
C25 C 1.0903(10) 0.2854(3) -0.0616(7) 0.0640(17) Uani 1 1 d . . . . .
C26 C 1.1424(8) 0.2308(2) -0.0996(6) 0.0499(13) Uani 1 1 d . . . . .
C27 C 1.0692(9) 0.1820(3) -0.0808(6) 0.0539(14) Uani 1 1 d . . . . .
H27 H 0.9792 0.1815 -0.0462 0.065 Uiso 1 1 calc R U . . .
C28 C 1.1314(7) 0.1343(2) -0.1141(5) 0.0464(13) Uani 1 1 d . . . . .
H28 H 1.0800 0.1019 -0.1046 0.056 Uiso 1 1 calc R U . . .
C29 C 1.2701(7) 0.1347(2) -0.1615(5) 0.0363(11) Uani 1 1 d . . . . .
C30 C 1.3371(9) 0.1825(3) -0.1819(7) 0.0588(16) Uani 1 1 d . . . . .
H30 H 1.4267 0.1831 -0.2168 0.071 Uiso 1 1 calc R U . . .
C31 C 1.2724(10) 0.2313(2) -0.1507(7) 0.0628(17) Uani 1 1 d . . . . .
H31 H 1.3193 0.2638 -0.1652 0.075 Uiso 1 1 calc R U . . .
C32 C 0.7493(10) 0.3213(3) 0.0723(8) 0.0699(18) Uani 1 1 d . . . . .
H32 H 0.6991 0.2872 0.0650 0.084 Uiso 1 1 calc R U . . .
C34 C 0.7381(12) 0.3488(4) 0.6040(10) 0.091(3) Uani 1 1 d . . . . .
H34 H 0.7821 0.3796 0.5778 0.109 Uiso 1 1 calc R U . . .
C50 C 0.5434(14) 0.1944(5) 0.1955(9) 0.114(4) Uani 1 1 d . . . . .
H50A H 0.6400 0.2155 0.2543 0.171 Uiso 1 1 calc R U . . .
H50B H 0.4632 0.1848 0.2390 0.171 Uiso 1 1 calc R U . . .
H50C H 0.4800 0.2150 0.1177 0.171 Uiso 1 1 calc R U . . .
C51 C 0.5600(16) 0.0943(4) 0.1819(10) 0.103(3) Uani 1 1 d . . . . .
H51A H 0.6260 0.0678 0.1548 0.154 Uiso 1 1 calc R U . . .
H51B H 0.4344 0.0899 0.1323 0.154 Uiso 1 1 calc R U . . .
H51C H 0.5828 0.0902 0.2744 0.154 Uiso 1 1 calc R U . . .
C52 C 0.5787(16) 0.4092(5) 0.7009(10) 0.105(3) Uani 1 1 d . . . . .
H52A H 0.5888 0.4349 0.6385 0.158 Uiso 1 1 calc R U . . .
H52B H 0.6558 0.4194 0.7884 0.158 Uiso 1 1 calc R U . . .
H52C H 0.4571 0.4080 0.6963 0.158 Uiso 1 1 calc R U . . .
C53 C 0.5490(13) 0.3108(4) 0.7085(9) 0.093(3) Uani 1 1 d . . . . .
H53A H 0.4335 0.3040 0.6417 0.140 Uiso 1 1 calc R U . . .
H53B H 0.5355 0.3185 0.7908 0.140 Uiso 1 1 calc R U . . .
H53C H 0.6236 0.2797 0.7186 0.140 Uiso 1 1 calc R U . . .
C54 C 0.8852(8) 0.4219(2) 0.0974(6) 0.0439(13) Uani 1 1 d . . . . .
H54 H 0.9315 0.4565 0.1063 0.053 Uiso 1 1 calc R U . . .
C55 C 0.1327(7) 0.5807(2) 0.4205(5) 0.0364(11) Uani 1 1 d . . . . .
H55 H 0.0881 0.5459 0.4145 0.044 Uiso 1 1 calc R U . . .
C56 C 0.0530(7) 0.6197(2) 0.4665(5) 0.0417(11) Uani 1 1 d . . . . .
H56 H -0.0414 0.6112 0.4932 0.050 Uiso 1 1 calc R U . . .
C57 C -0.0255(6) 0.5316(3) -0.1479(4) 0.0511(12) Uani 1 1 d . . . . .
H57 H -0.0518 0.5519 -0.0857 0.061 Uiso 1 1 calc R U . . .
C58 C 0.3646(7) 0.4192(2) 0.3236(5) 0.0312(11) Uani 1 1 d . . . . .
C59 C 0.6561(8) 0.5831(2) 0.1918(5) 0.0343(13) Uani 1 1 d . . . . .
C60 C 0.6819(9) 0.3632(3) 0.1192(8) 0.0651(18) Uani 1 1 d . . . . .
H60 H 0.5825 0.3567 0.1414 0.078 Uiso 1 1 calc R U . . .
N1 N 0.6307(8) 0.3563(3) 0.6699(6) 0.0703(15) Uani 1 1 d . . . . .
N2 N 0.6142(8) 0.1463(3) 0.1587(7) 0.0746(16) Uani 1 1 d . . . . .
N3 N 0.2711(5) 0.58918(17) 0.3833(4) 0.0316(9) Uani 1 1 d . . . . .
N4 N 0.0399(6) 0.7169(2) 0.5132(6) 0.0482(11) Uani 1 1 d . . . . .
N5 N 0.7475(6) 0.41321(18) 0.1359(4) 0.0351(10) Uani 1 1 d . . . . .
N6 N 0.9646(7) 0.2855(2) -0.0087(6) 0.0540(13) Uani 1 1 d . . . . .
O1 O -0.1903(4) 0.47624(17) -0.5959(3) 0.0447(8) Uani 1 1 d . . . . .
O2 O 0.7234(4) 0.53983(16) 0.1724(3) 0.0445(8) Uani 1 1 d . . . . .
O3 O 0.2137(4) 0.52682(19) 0.1143(3) 0.0502(9) Uani 1 1 d . . . . .
O4 O 0.4049(4) 0.47800(16) 0.0530(3) 0.0506(10) Uani 1 1 d . . . . .
O5 O -0.3816(4) 0.52375(15) -0.5353(3) 0.0487(9) Uani 1 1 d . . . . .
O9 O 0.4909(6) 0.41575(16) 0.2850(4) 0.0484(10) Uani 1 1 d . . . . .
O10 O 0.5311(5) 0.58644(16) 0.2327(4) 0.0451(10) Uani 1 1 d . . . . .
O12 O 1.1625(10) 0.3258(2) -0.0777(8) 0.116(3) Uani 1 1 d . . . . .
O20 O 0.7845(9) 0.3069(3) 0.5745(8) 0.102(2) Uani 1 1 d . . . . .
O21 O 0.7706(10) 0.1955(3) 0.0606(9) 0.120(3) Uani 1 1 d . . . . .
O22 O 0.2964(4) 0.46254(16) 0.3456(3) 0.0443(8) Uani 1 1 d . . . . .
O23 O -0.1589(9) 0.6758(2) 0.5841(8) 0.102(2) Uani 1 1 d . . . . .
Zn1 Zn 0.63505(6) 0.46886(2) 0.21469(4) 0.02430(13) Uani 1 1 d . . . . .
Zn2 Zn 0.38697(6) 0.53367(2) 0.30442(4) 0.02377(13) Uani 1 1 d . . . . .
H4N H 0.089(7) 0.746(3) 0.509(5) 0.036 Uiso 1 1 d . U . . .
H6N H 0.911(7) 0.257(3) -0.003(5) 0.036 Uiso 1 1 d . U . . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
C2 O21 1.243(11) . ?
C2 N2 1.307(11) . ?
C2 H2 0.9300 . ?
C4 O4 1.250(6) . ?
C4 O3 1.262(6) . ?
C4 C5 1.496(5) . ?
C5 C57 1.387(7) . ?
C5 C10 1.395(7) . ?
C6 C57 1.376(6) . ?
C6 C7 1.391(7) . ?
C6 H6 0.9300 . ?
C7 C9 1.385(7) . ?
C7 C8 1.505(5) . ?
C8 O5 1.245(6) . ?
C8 O1 1.252(5) . ?
C9 C10 1.378(6) . ?
C9 H9 0.9300 . ?
C10 H10 0.9300 . ?
C11 N3 1.346(7) . ?
C11 C12 1.364(8) . ?
C11 H11 0.9300 . ?
C12 C13 1.390(8) . ?
C12 H12 0.9300 . ?
C13 C56 1.391(7) . ?
C13 N4 1.396(7) . ?
C14 O23 1.205(8) . ?
C14 N4 1.373(8) . ?
C14 C15 1.496(7) 2_556 ?
C15 C20 1.374(8) . ?
C15 C21 1.396(8) . ?
C15 C14 1.496(7) 2_546 ?
C18 C19 1.372(7) . ?
C18 C22 1.390(8) . ?
C18 C58 1.521(7) . ?
C19 C20 1.395(8) . ?
C19 H19 0.9300 . ?
C20 H20 0.9300 . ?
C21 C22 1.347(8) . ?
C21 H21 0.9300 . ?
C22 H22 0.9300 . ?
C23 C24 1.396(8) . ?
C23 C54 1.402(8) . ?
C23 H23 0.9300 . ?
C24 C32 1.399(9) . ?
C24 N6 1.411(7) . ?
C25 O12 1.206(9) . ?
C25 N6 1.334(9) . ?
C25 C26 1.524(8) . ?
C26 C31 1.351(10) . ?
C26 C27 1.397(9) . ?
C27 C28 1.387(8) . ?
C27 H27 0.9300 . ?
C28 C29 1.390(7) . ?
C28 H28 0.9300 . ?
C29 C30 1.356(9) . ?
C29 C59 1.501(7) 2_745 ?
C30 C31 1.411(8) . ?
C30 H30 0.9300 . ?
C31 H31 0.9300 . ?
C32 C60 1.359(9) . ?
C32 H32 0.9300 . ?
C34 O20 1.192(11) . ?
C34 N1 1.323(11) . ?
C34 H34 0.9300 . ?
C50 N2 1.444(12) . ?
C50 H50A 0.9600 . ?
C50 H50B 0.9600 . ?
C50 H50C 0.9600 . ?
C51 N2 1.418(13) . ?
C51 H51A 0.9600 . ?
C51 H51B 0.9600 . ?
C51 H51C 0.9600 . ?
C52 N1 1.457(12) . ?
C52 H52A 0.9600 . ?
C52 H52B 0.9600 . ?
C52 H52C 0.9600 . ?
C53 N1 1.448(10) . ?
C53 H53A 0.9600 . ?
C53 H53B 0.9600 . ?
C53 H53C 0.9600 . ?
C54 N5 1.337(7) . ?
C54 H54 0.9300 . ?
C55 N3 1.333(7) . ?
C55 C56 1.356(8) . ?
C55 H55 0.9300 . ?
C56 H56 0.9300 . ?
C57 H57 0.9300 . ?
C58 O9 1.235(6) . ?
C58 O22 1.272(7) . ?
C59 O10 1.241(7) . ?
C59 O2 1.258(8) . ?
C59 C29 1.501(7) 2_755 ?
C60 N5 1.337(8) . ?
C60 H60 0.9300 . ?
N3 Zn2 2.025(4) . ?
N4 H4N 0.84(6) . ?
N5 Zn1 2.010(4) . ?
N6 H6N 0.83(6) . ?
O1 Zn1 2.031(3) 1_454 ?
O2 Zn1 2.019(4) . ?
O3 Zn2 2.033(3) . ?
O4 Zn1 2.044(3) . ?
O5 Zn2 2.044(3) 1_454 ?
O9 Zn1 2.080(4) . ?
O10 Zn2 2.084(4) . ?
O22 Zn2 2.026(4) . ?
Zn1 O1 2.031(3) 1_656 ?
Zn1 Zn2 2.9936(5) . ?
Zn2 O5 2.044(3) 1_656 ?

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
O21 C2 N2 126.9(8) . . ?
O21 C2 H2 116.6 . . ?
N2 C2 H2 116.6 . . ?
O4 C4 O3 126.5(4) . . ?
O4 C4 C5 116.4(4) . . ?
O3 C4 C5 117.0(4) . . ?
C57 C5 C10 118.5(4) . . ?
C57 C5 C4 121.4(4) . . ?
C10 C5 C4 120.0(4) . . ?
C57 C6 C7 120.5(4) . . ?
C57 C6 H6 119.8 . . ?
C7 C6 H6 119.8 . . ?
C9 C7 C6 118.8(4) . . ?
C9 C7 C8 120.8(4) . . ?
C6 C7 C8 120.4(4) . . ?
O5 C8 O1 125.9(4) . . ?
O5 C8 C7 116.5(4) . . ?
O1 C8 C7 117.6(4) . . ?
C10 C9 C7 120.9(4) . . ?
C10 C9 H9 119.6 . . ?
C7 C9 H9 119.6 . . ?
C9 C10 C5 120.4(4) . . ?
C9 C10 H10 119.8 . . ?
C5 C10 H10 119.8 . . ?
N3 C11 C12 122.7(5) . . ?
N3 C11 H11 118.6 . . ?
C12 C11 H11 118.6 . . ?
C11 C12 C13 120.0(5) . . ?
C11 C12 H12 120.0 . . ?
C13 C12 H12 120.0 . . ?
C12 C13 C56 116.7(5) . . ?
C12 C13 N4 117.3(5) . . ?
C56 C13 N4 126.0(5) . . ?
O23 C14 N4 122.1(5) . . ?
O23 C14 C15 122.9(5) . 2_556 ?
N4 C14 C15 115.1(5) . 2_556 ?
C20 C15 C21 118.0(5) . . ?
C20 C15 C14 126.2(5) . 2_546 ?
C21 C15 C14 115.7(5) . 2_546 ?
C19 C18 C22 118.9(5) . . ?
C19 C18 C58 121.9(5) . . ?
C22 C18 C58 119.2(5) . . ?
C18 C19 C20 119.9(5) . . ?
C18 C19 H19 120.0 . . ?
C20 C19 H19 120.0 . . ?
C15 C20 C19 121.0(5) . . ?
C15 C20 H20 119.5 . . ?
C19 C20 H20 119.5 . . ?
C22 C21 C15 121.1(5) . . ?
C22 C21 H21 119.4 . . ?
C15 C21 H21 119.4 . . ?
C21 C22 C18 121.1(5) . . ?
C21 C22 H22 119.5 . . ?
C18 C22 H22 119.5 . . ?
C24 C23 C54 116.6(5) . . ?
C24 C23 H23 121.7 . . ?
C54 C23 H23 121.7 . . ?
C23 C24 C32 119.2(5) . . ?
C23 C24 N6 124.7(5) . . ?
C32 C24 N6 116.1(6) . . ?
O12 C25 N6 122.9(6) . . ?
O12 C25 C26 120.7(6) . . ?
N6 C25 C26 116.5(6) . . ?
C31 C26 C27 119.9(5) . . ?
C31 C26 C25 115.8(6) . . ?
C27 C26 C25 124.3(5) . . ?
C28 C27 C26 119.6(5) . . ?
C28 C27 H27 120.2 . . ?
C26 C27 H27 120.2 . . ?
C27 C28 C29 120.4(6) . . ?
C27 C28 H28 119.8 . . ?
C29 C28 H28 119.8 . . ?
C30 C29 C28 119.2(5) . . ?
C30 C29 C59 120.1(5) . 2_745 ?
C28 C29 C59 120.7(5) . 2_745 ?
C29 C30 C31 120.8(6) . . ?
C29 C30 H30 119.6 . . ?
C31 C30 H30 119.6 . . ?
C26 C31 C30 120.0(6) . . ?
C26 C31 H31 120.0 . . ?
C30 C31 H31 120.0 . . ?
C60 C32 C24 118.3(6) . . ?
C60 C32 H32 120.8 . . ?
C24 C32 H32 120.8 . . ?
O20 C34 N1 126.9(8) . . ?
O20 C34 H34 116.6 . . ?
N1 C34 H34 116.6 . . ?
N2 C50 H50A 109.5 . . ?
N2 C50 H50B 109.5 . . ?
H50A C50 H50B 109.5 . . ?
N2 C50 H50C 109.5 . . ?
H50A C50 H50C 109.5 . . ?
H50B C50 H50C 109.5 . . ?
N2 C51 H51A 109.5 . . ?
N2 C51 H51B 109.5 . . ?
H51A C51 H51B 109.5 . . ?
N2 C51 H51C 109.5 . . ?
H51A C51 H51C 109.5 . . ?
H51B C51 H51C 109.5 . . ?
N1 C52 H52A 109.5 . . ?
N1 C52 H52B 109.5 . . ?
H52A C52 H52B 109.5 . . ?
N1 C52 H52C 109.5 . . ?
H52A C52 H52C 109.5 . . ?
H52B C52 H52C 109.5 . . ?
N1 C53 H53A 109.5 . . ?
N1 C53 H53B 109.5 . . ?
H53A C53 H53B 109.5 . . ?
N1 C53 H53C 109.5 . . ?
H53A C53 H53C 109.5 . . ?
H53B C53 H53C 109.5 . . ?
N5 C54 C23 124.8(5) . . ?
N5 C54 H54 117.6 . . ?
C23 C54 H54 117.6 . . ?
N3 C55 C56 123.9(5) . . ?
N3 C55 H55 118.0 . . ?
C56 C55 H55 118.0 . . ?
C55 C56 C13 119.6(5) . . ?
C55 C56 H56 120.2 . . ?
C13 C56 H56 120.2 . . ?
C6 C57 C5 121.0(4) . . ?
C6 C57 H57 119.5 . . ?
C5 C57 H57 119.5 . . ?
O9 C58 O22 126.0(5) . . ?
O9 C58 C18 118.3(5) . . ?
O22 C58 C18 115.7(5) . . ?
O10 C59 O2 124.8(5) . . ?
O10 C59 C29 117.3(5) . 2_755 ?
O2 C59 C29 117.9(5) . 2_755 ?
N5 C60 C32 125.0(6) . . ?
N5 C60 H60 117.5 . . ?
C32 C60 H60 117.5 . . ?
C34 N1 C53 120.2(8) . . ?
C34 N1 C52 123.6(8) . . ?
C53 N1 C52 116.1(7) . . ?
C2 N2 C51 120.5(8) . . ?
C2 N2 C50 117.3(8) . . ?
C51 N2 C50 121.9(8) . . ?
C55 N3 C11 116.9(4) . . ?
C55 N3 Zn2 125.8(4) . . ?
C11 N3 Zn2 117.3(4) . . ?
C14 N4 C13 127.1(5) . . ?
C14 N4 H4N 118(4) . . ?
C13 N4 H4N 115(4) . . ?
C60 N5 C54 116.0(5) . . ?
C60 N5 Zn1 118.9(4) . . ?
C54 N5 Zn1 125.2(4) . . ?
C25 N6 C24 126.8(6) . . ?
C25 N6 H6N 121(4) . . ?
C24 N6 H6N 112(4) . . ?
C8 O1 Zn1 120.1(3) . 1_454 ?
C59 O2 Zn1 120.2(3) . . ?
C4 O3 Zn2 120.1(3) . . ?
C4 O4 Zn1 134.7(3) . . ?
C8 O5 Zn2 135.9(3) . 1_454 ?
C58 O9 Zn1 135.9(4) . . ?
C59 O10 Zn2 136.6(4) . . ?
C58 O22 Zn2 119.0(3) . . ?
N5 Zn1 O2 104.78(18) . . ?
N5 Zn1 O1 104.13(16) . 1_656 ?
O2 Zn1 O1 88.99(16) . 1_656 ?
N5 Zn1 O4 96.65(15) . . ?
O2 Zn1 O4 89.38(15) . . ?
O1 Zn1 O4 158.87(15) 1_656 . ?
N5 Zn1 O9 96.7(2) . . ?
O2 Zn1 O9 158.42(15) . . ?
O1 Zn1 O9 87.40(16) 1_656 . ?
O4 Zn1 O9 86.42(17) . . ?
N5 Zn1 Zn2 165.53(13) . . ?
O2 Zn1 Zn2 86.26(10) . . ?
O1 Zn1 Zn2 85.10(10) 1_656 . ?
O4 Zn1 Zn2 73.78(10) . . ?
O9 Zn1 Zn2 72.24(12) . . ?
N3 Zn2 O22 104.12(18) . . ?
N3 Zn2 O3 103.86(15) . . ?
O22 Zn2 O3 89.12(17) . . ?
N3 Zn2 O5 97.82(15) . 1_656 ?
O22 Zn2 O5 89.63(15) . 1_656 ?
O3 Zn2 O5 157.91(16) . 1_656 ?
N3 Zn2 O10 97.72(19) . . ?
O22 Zn2 O10 158.14(15) . . ?
O3 Zn2 O10 86.47(17) . . ?
O5 Zn2 O10 86.53(16) 1_656 . ?
N3 Zn2 Zn1 166.19(12) . . ?
O22 Zn2 Zn1 86.42(10) . . ?
O3 Zn2 Zn1 84.92(11) . . ?
O5 Zn2 Zn1 72.99(10) 1_656 . ?
O10 Zn2 Zn1 71.88(11) . . ?

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 C4 C5 C57 -170.5(5) . . . . ?
O3 C4 C5 C57 7.6(7) . . . . ?
O4 C4 C5 C10 6.5(7) . . . . ?
O3 C4 C5 C10 -175.5(5) . . . . ?
C57 C6 C7 C9 -1.2(9) . . . . ?
C57 C6 C7 C8 176.1(5) . . . . ?
C9 C7 C8 O5 170.5(5) . . . . ?
C6 C7 C8 O5 -6.7(7) . . . . ?
C9 C7 C8 O1 -9.1(7) . . . . ?
C6 C7 C8 O1 173.7(5) . . . . ?
C6 C7 C9 C10 0.7(9) . . . . ?
C8 C7 C9 C10 -176.6(5) . . . . ?
C7 C9 C10 C5 -0.1(9) . . . . ?
C57 C5 C10 C9 0.0(9) . . . . ?
C4 C5 C10 C9 -177.1(5) . . . . ?
N3 C11 C12 C13 1.5(11) . . . . ?
C11 C12 C13 C56 1.7(9) . . . . ?
C11 C12 C13 N4 -178.6(6) . . . . ?
C22 C18 C19 C20 1.8(8) . . . . ?
C58 C18 C19 C20 -179.8(5) . . . . ?
C21 C15 C20 C19 -1.4(9) . . . . ?
C14 C15 C20 C19 177.0(6) 2_546 . . . ?
C18 C19 C20 C15 -0.2(9) . . . . ?
C20 C15 C21 C22 1.5(10) . . . . ?
C14 C15 C21 C22 -177.0(6) 2_546 . . . ?
C15 C21 C22 C18 0.0(10) . . . . ?
C19 C18 C22 C21 -1.6(9) . . . . ?
C58 C18 C22 C21 179.9(6) . . . . ?
C54 C23 C24 C32 2.9(9) . . . . ?
C54 C23 C24 N6 -176.7(6) . . . . ?
O12 C25 C26 C31 0.3(11) . . . . ?
N6 C25 C26 C31 -178.7(6) . . . . ?
O12 C25 C26 C27 178.1(8) . . . . ?
N6 C25 C26 C27 -0.9(10) . . . . ?
C31 C26 C27 C28 0.3(10) . . . . ?
C25 C26 C27 C28 -177.4(6) . . . . ?
C26 C27 C28 C29 2.3(9) . . . . ?
C27 C28 C29 C30 -3.7(8) . . . . ?
C27 C28 C29 C59 177.2(5) . . . 2_745 ?
C28 C29 C30 C31 2.5(9) . . . . ?
C59 C29 C30 C31 -178.3(6) 2_745 . . . ?
C27 C26 C31 C30 -1.5(10) . . . . ?
C25 C26 C31 C30 176.4(6) . . . . ?
C29 C30 C31 C26 0.1(11) . . . . ?
C23 C24 C32 C60 -1.6(11) . . . . ?
N6 C24 C32 C60 178.0(7) . . . . ?
C24 C23 C54 N5 -1.5(9) . . . . ?
N3 C55 C56 C13 1.7(9) . . . . ?
C12 C13 C56 C55 -3.2(8) . . . . ?
N4 C13 C56 C55 177.1(5) . . . . ?
C7 C6 C57 C5 1.1(9) . . . . ?
C10 C5 C57 C6 -0.5(9) . . . . ?
C4 C5 C57 C6 176.5(5) . . . . ?
C19 C18 C58 O9 178.4(5) . . . . ?
C22 C18 C58 O9 -3.2(7) . . . . ?
C19 C18 C58 O22 0.6(7) . . . . ?
C22 C18 C58 O22 179.1(5) . . . . ?
C24 C32 C60 N5 -1.5(12) . . . . ?
O20 C34 N1 C53 -3.2(16) . . . . ?
O20 C34 N1 C52 -179.3(10) . . . . ?
O21 C2 N2 C51 176.1(11) . . . . ?
O21 C2 N2 C50 1.3(16) . . . . ?
C56 C55 N3 C11 1.5(8) . . . . ?
C56 C55 N3 Zn2 -176.4(4) . . . . ?
C12 C11 N3 C55 -3.1(9) . . . . ?
C12 C11 N3 Zn2 174.9(5) . . . . ?
O23 C14 N4 C13 2.2(11) . . . . ?
C15 C14 N4 C13 -178.3(5) 2_556 . . . ?
C12 C13 N4 C14 -173.0(6) . . . . ?
C56 C13 N4 C14 6.6(10) . . . . ?
C32 C60 N5 C54 3.0(11) . . . . ?
C32 C60 N5 Zn1 -177.2(6) . . . . ?
C23 C54 N5 C60 -1.4(9) . . . . ?
C23 C54 N5 Zn1 178.8(4) . . . . ?
O12 C25 N6 C24 0.3(13) . . . . ?
C26 C25 N6 C24 179.3(6) . . . . ?
C23 C24 N6 C25 -8.0(11) . . . . ?
C32 C24 N6 C25 172.4(7) . . . . ?
O5 C8 O1 Zn1 -3.0(7) . . . 1_454 ?
C7 C8 O1 Zn1 176.5(3) . . . 1_454 ?
O10 C59 O2 Zn1 -2.3(7) . . . . ?
C29 C59 O2 Zn1 178.6(3) 2_755 . . . ?
O4 C4 O3 Zn2 1.1(8) . . . . ?
C5 C4 O3 Zn2 -176.7(3) . . . . ?
O3 C4 O4 Zn1 -1.8(9) . . . . ?
C5 C4 O4 Zn1 176.0(3) . . . . ?
O1 C8 O5 Zn2 2.8(9) . . . 1_454 ?
C7 C8 O5 Zn2 -176.8(3) . . . 1_454 ?
O22 C58 O9 Zn1 -9.2(9) . . . . ?
C18 C58 O9 Zn1 173.3(3) . . . . ?
O2 C59 O10 Zn2 6.9(8) . . . . ?
C29 C59 O10 Zn2 -174.1(3) 2_755 . . . ?
O9 C58 O22 Zn2 4.2(7) . . . . ?
C18 C58 O22 Zn2 -178.2(3) . . . . ?

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
C11 H11 O10 0.93 2.46 3.069(7) 122.9 .
C12 H12 O20 0.93 2.37 3.144(9) 140.1 2_656
C23 H23 O12 0.93 2.24 2.801(8) 118.2 .
C32 H32 O21 0.93 2.36 3.142(10) 141.5 .
C56 H56 O23 0.93 2.27 2.845(8) 119.6 .
C60 H60 O9 0.93 2.45 3.058(8) 123.3 .
N4 H4N O20 0.84(6) 2.20(6) 2.985(8) 157(5) 2_656
N6 H6N O21 0.83(6) 2.17(6) 2.980(9) 164(5) .

_refine_diff_density_max         0.841
_refine_diff_density_min         -0.385
_refine_diff_density_rms         0.094

####################################################################### 
# 
# 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_Compound2
_database_code_depnum_ccdc_archive 'CCDC 1414612'
_audit_update_record             
;
2015-09-17 deposited with the CCDC.
2015-09-28 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C26 H18 Cu N4 O6, 4(C3 H7 N O), H2 O'
_chemical_formula_sum            'C38 H48 Cu N8 O11'
_chemical_formula_weight         856.38

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'

_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 21/n'
_space_group_name_Hall           '-P 2yn'

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

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

_cell_length_a                   8.3259(14)
_cell_length_b                   22.773(4)
_cell_length_c                   20.105(3)
_cell_angle_alpha                90
_cell_angle_beta                 93.700(5)
_cell_angle_gamma                90
_cell_volume                     3804.1(11)
_cell_formula_units_Z            4
_cell_measurement_temperature    150(2)
_cell_measurement_reflns_used    9936
_cell_measurement_theta_min      2.22
_cell_measurement_theta_max      25.40

_exptl_crystal_description       block
_exptl_crystal_colour            blue
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.495
_exptl_crystal_F_000             1796
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.290
_exptl_crystal_size_mid          0.200
_exptl_crystal_size_min          0.120
_exptl_absorpt_coefficient_mu    0.648
_shelx_estimated_absorpt_T_min   0.834
_shelx_estimated_absorpt_T_max   0.926
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.859
_exptl_absorpt_correction_T_max  0.930
_exptl_absorpt_process_details   sadabs
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      150(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            43898
_diffrn_reflns_av_unetI/netI     0.0902
_diffrn_reflns_av_R_equivalents  0.1053
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       -27
_diffrn_reflns_limit_k_max       27
_diffrn_reflns_limit_l_min       -24
_diffrn_reflns_limit_l_max       24
_diffrn_reflns_theta_min         2.592
_diffrn_reflns_theta_max         25.501
_diffrn_reflns_theta_full        25.000
_diffrn_measured_fraction_theta_max 0.984
_diffrn_measured_fraction_theta_full 0.989
_diffrn_reflns_Laue_measured_fraction_max 0.984
_diffrn_reflns_Laue_measured_fraction_full 0.989
_diffrn_reflns_point_group_measured_fraction_max 0.984
_diffrn_reflns_point_group_measured_fraction_full 0.989
_reflns_number_total             6972
_reflns_number_gt                4604
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

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

 The aromatic carbons C16 > C20, as well as the C27 > C29
 and N6 atoms of the crystallization dmf molecule have large
 ADPs. No obvious residual electron density around such atoms
 could be localized when they were refined with isotopic ADPs,
 and the model could not be improved by considering disorder
 over two orientations and refinement with the use of PART
 instructions. The option was to use ISOR restrains together
 with (in the aromatic carbons) the rigid bond retrains DELU
 and EADP, despite the increase in the final R1 factor.
 The hydrogen atoms bound to the N2 and N4 atoms were located
 from the final difference Fourier map and refined with their
 positions fixed (N4) or restrained with DFIX (N2); the Uiso
 of both H-atoms were defined as 1.5Ueq of the parent N-atoms.
;

_computing_data_collection       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SIR97 (Giacovazzo et al, 1999)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    'Mercury CSD 3.5.1, 2008'
_computing_publication_material  'WinGX publication routines (Farrugia, 1999)'
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.1135P)²+8.8555P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         6972
_refine_ls_number_parameters     360
_refine_ls_number_restraints     80
_refine_ls_R_factor_all          0.1243
_refine_ls_R_factor_gt           0.0834
_refine_ls_wR_factor_ref         0.2268
_refine_ls_wR_factor_gt          0.2110
_refine_ls_goodness_of_fit_ref   1.057
_refine_ls_restrained_S_all      1.098
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000

loop_
_platon_squeeze_void_nr
_platon_squeeze_void_average_x
_platon_squeeze_void_average_y
_platon_squeeze_void_average_z
_platon_squeeze_void_volume
_platon_squeeze_void_count_electrons
_platon_squeeze_void_content
1 -0.085 0.000 0.000 633 281 ' '
2 -0.001 0.500 0.500 633 281 ' '
_platon_squeeze_void_probe_radius 1.20
_platon_squeeze_details          
;
 The Platon SQUEEZE procedure was applied to recover 562 electrons per
 unit cell in a void (total volume 1266 A^3), that is, 141 electrons
 per formula unit. On the basis of microanalytical data, the void content
 may include 1 water and 3 dmf molecules, i.e., a total of 130 electrons not
 far from the values estimated by SQUEEZE. Those solvent molecules have
 been included in the formula for the calculation of intensive  properties,
 thus justifying the checkcif report allerts CHEMW03_ALERT_2_A and
 DIFF003_ALERT_1_A. 
 PLATON Reference : Spek, A.L. (2003), J.Appl.Cryst. 36, 7-13.
;

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C 0.6920(6) 0.4489(2) 0.5656(2) 0.0189(11) Uani 1 1 d . . . . .
C2 C 0.7487(6) 0.4062(2) 0.6199(3) 0.0207(12) Uani 1 1 d . . . . .
C3 C 0.6465(7) 0.3619(2) 0.6378(3) 0.0277(13) Uani 1 1 d . . . . .
H3 H 0.5442 0.3576 0.6145 0.033 Uiso 1 1 calc R U . . .
C4 C 0.6923(7) 0.3236(2) 0.6897(3) 0.0281(13) Uani 1 1 d . . . . .
H4 H 0.6193 0.2944 0.7029 0.034 Uiso 1 1 calc R U . . .
C5 C 0.8413(7) 0.3278(2) 0.7216(3) 0.0259(13) Uani 1 1 d . . . . .
C6 C 0.9467(7) 0.3716(2) 0.7042(3) 0.0274(13) Uani 1 1 d . . . . .
H6 H 1.0496 0.3750 0.7272 0.033 Uiso 1 1 calc R U . . .
C7 C 0.9007(7) 0.4108(2) 0.6523(3) 0.0274(13) Uani 1 1 d . . . . .
H7 H 0.9733 0.4403 0.6396 0.033 Uiso 1 1 calc R U . . .
C8 C 0.8980(7) 0.2880(2) 0.7779(3) 0.0303(14) Uani 1 1 d . . . . .
C9 C 0.5664(7) 0.6500(2) 0.5693(3) 0.0279(13) Uani 1 1 d . . . . .
H9 H 0.4921 0.6515 0.5315 0.034 Uiso 1 1 calc R U . . .
C10 C 0.5560(7) 0.6931(2) 0.6167(3) 0.0284(14) Uani 1 1 d . . . . .
H10 H 0.4788 0.7237 0.6110 0.034 Uiso 1 1 calc R U . . .
C11 C 0.6626(7) 0.6908(2) 0.6738(3) 0.0260(13) Uani 1 1 d . . . . .
C12 C 0.7666(7) 0.6426(2) 0.6802(3) 0.0276(13) Uani 1 1 d . . . . .
H12 H 0.8358 0.6380 0.7193 0.033 Uiso 1 1 calc R U . . .
C13 C 0.7686(6) 0.6021(2) 0.6300(3) 0.0244(12) Uani 1 1 d . . . . .
H13 H 0.8400 0.5697 0.6356 0.029 Uiso 1 1 calc R U . . .
C14 C 0.8519(7) 0.6567(2) 0.4524(3) 0.0235(12) Uani 1 1 d . . . . .
C15 C 0.8564(6) 0.7130(2) 0.4112(3) 0.0225(12) Uani 1 1 d . . . . .
C16 C 0.7476(10) 0.7245(4) 0.3610(4) 0.0717(12) Uani 1 1 d . U . . .
H16 H 0.6603 0.6980 0.3532 0.086 Uiso 1 1 calc R U . . .
C17 C 0.7556(10) 0.7724(4) 0.3206(4) 0.0717(12) Uani 1 1 d . U . . .
H17 H 0.6807 0.7760 0.2831 0.086 Uiso 1 1 calc R U . . .
C18 C 0.8663(10) 0.8146(4) 0.3323(4) 0.0717(12) Uani 1 1 d . U . . .
C19 C 0.9776(10) 0.8031(4) 0.3828(4) 0.0717(12) Uani 1 1 d . U . . .
H19 H 1.0599 0.8312 0.3932 0.086 Uiso 1 1 calc R U . . .
C20 C 0.9754(10) 0.7518(4) 0.4200(4) 0.0717(12) Uani 1 1 d . U . . .
H20 H 1.0609 0.7443 0.4525 0.086 Uiso 1 1 calc R U . . .
C21 C 0.8807(9) 0.8681(3) 0.2927(3) 0.0391(16) Uani 1 1 d . . . . .
C22 C 0.7860(7) 0.9150(2) 0.1847(3) 0.0269(13) Uani 1 1 d . . . . .
C23 C 0.6873(7) 0.9066(2) 0.1271(3) 0.0286(14) Uani 1 1 d . . . . .
H23 H 0.6251 0.8717 0.1219 0.034 Uiso 1 1 calc R U . . .
C24 C 0.6786(7) 0.9485(2) 0.0773(3) 0.0251(12) Uani 1 1 d . . . . .
H24 H 0.6137 0.9412 0.0375 0.030 Uiso 1 1 calc R U . . .
C25 C 0.8534(7) 1.0088(2) 0.1404(3) 0.0269(13) Uani 1 1 d . . . . .
H25 H 0.9118 1.0445 0.1452 0.032 Uiso 1 1 calc R U . . .
C26 C 0.8686(7) 0.9690(2) 0.1917(3) 0.0302(14) Uani 1 1 d . . . . .
H26 H 0.9335 0.9776 0.2311 0.036 Uiso 1 1 calc R U . . .
C27 C 0.468(2) 0.8213(7) 0.5107(7) 0.184(7) Uani 1 1 d . U . . .
H27A H 0.4622 0.8551 0.5405 0.277 Uiso 1 1 calc R U . . .
H27B H 0.5759 0.8037 0.5165 0.277 Uiso 1 1 calc R U . . .
H27C H 0.3876 0.7921 0.5216 0.277 Uiso 1 1 calc R U . . .
C28 C 0.487(2) 0.8968(5) 0.4345(6) 0.147(5) Uani 1 1 d . U . . .
H28A H 0.5046 0.9032 0.3873 0.221 Uiso 1 1 calc R U . . .
H28B H 0.5873 0.9043 0.4614 0.221 Uiso 1 1 calc R U . . .
H28C H 0.4032 0.9236 0.4482 0.221 Uiso 1 1 calc R U . . .
C29 C 0.3824(15) 0.8069(5) 0.3931(5) 0.104(4) Uani 1 1 d . U . . .
H29 H 0.3459 0.7688 0.4040 0.125 Uiso 1 1 calc R U . . .
N1 N 0.6738(5) 0.60580(18) 0.5726(2) 0.0200(10) Uani 1 1 d . . . . .
N2 N 0.8284(6) 0.2333(2) 0.7758(2) 0.0299(12) Uani 1 1 d D . . . .
N3 N 0.7614(5) 1.00038(18) 0.0839(2) 0.0233(10) Uani 1 1 d . . . . .
N4 N 0.7926(6) 0.8705(2) 0.2323(2) 0.0334(12) Uani 1 1 d . . . . .
N6 N 0.4391(11) 0.8397(3) 0.4438(3) 0.081(2) Uani 1 1 d . U . . .
O1 O 0.7844(5) 0.49285(15) 0.55803(18) 0.0262(9) Uani 1 1 d . . . . .
O2 O 0.5642(4) 0.43922(15) 0.53291(18) 0.0243(9) Uani 1 1 d . . . . .
O3 O 0.7314(4) 0.62349(15) 0.43695(17) 0.0225(8) Uani 1 1 d . . . . .
O4 O 0.9581(5) 0.64730(19) 0.4958(2) 0.0401(11) Uani 1 1 d . . . . .
O5 O 0.9645(8) 0.9096(2) 0.3127(2) 0.0659(16) Uani 1 1 d . U . . .
O6 O 0.9949(6) 0.3032(2) 0.8218(2) 0.0486(13) Uani 1 1 d . U . . .
O8 O 0.3716(7) 0.8200(2) 0.3342(2) 0.0586(14) Uani 1 1 d . U . . .
Cu1 Cu 0.71295(8) 0.55428(3) 0.49448(3) 0.0197(2) Uani 1 1 d . . . . .
H2N H 0.770(6) 0.221(2) 0.7402(19) 0.030 Uiso 1 1 d D U . . .
H4N H 0.7305 0.8400 0.2229 0.030 Uiso 1 1 d . U . . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
C1 O2 1.235(6) . ?
C1 O1 1.277(6) . ?
C1 C2 1.513(7) . ?
C2 C3 1.382(8) . ?
C2 C7 1.390(8) . ?
C3 C4 1.396(7) . ?
C3 H3 0.9500 . ?
C4 C5 1.363(8) . ?
C4 H4 0.9500 . ?
C5 C6 1.388(8) . ?
C5 C8 1.502(7) . ?
C6 C7 1.407(7) . ?
C6 H6 0.9500 . ?
C7 H7 0.9500 . ?
C8 O6 1.208(7) . ?
C8 N2 1.374(7) . ?
C9 N1 1.345(7) . ?
C9 C10 1.373(7) . ?
C9 H9 0.9500 . ?
C10 C11 1.407(8) . ?
C10 H10 0.9500 . ?
C11 N2 1.399(7) 2_656 ?
C11 C12 1.398(8) . ?
C12 C13 1.367(7) . ?
C12 H12 0.9500 . ?
C13 N1 1.358(7) . ?
C13 H13 0.9500 . ?
C14 O4 1.220(6) . ?
C14 O3 1.278(6) . ?
C14 C15 1.527(7) . ?
C15 C20 1.332(9) . ?
C15 C16 1.338(9) . ?
C16 C17 1.365(9) . ?
C16 H16 0.9500 . ?
C17 C18 1.342(10) . ?
C17 H17 0.9500 . ?
C18 C19 1.355(10) . ?
C18 C21 1.466(9) . ?
C19 C20 1.387(10) . ?
C19 H19 0.9500 . ?
C20 H20 0.9500 . ?
C21 O5 1.227(8) . ?
C21 N4 1.378(8) . ?
C22 C23 1.390(8) . ?
C22 N4 1.393(7) . ?
C22 C26 1.411(8) . ?
C23 C24 1.382(8) . ?
C23 H23 0.9500 . ?
C24 N3 1.369(7) . ?
C24 H24 0.9500 . ?
C25 N3 1.341(7) . ?
C25 C26 1.372(8) . ?
C25 H25 0.9500 . ?
C26 H26 0.9500 . ?
C27 N6 1.417(14) . ?
C27 H27A 0.9800 . ?
C27 H27B 0.9800 . ?
C27 H27C 0.9800 . ?
C28 N6 1.375(13) . ?
C28 H28A 0.9800 . ?
C28 H28B 0.9800 . ?
C28 H28C 0.9800 . ?
C29 O8 1.220(11) . ?
C29 N6 1.326(12) . ?
C29 H29 0.9500 . ?
N1 Cu1 2.004(4) . ?
N2 C11 1.399(7) 2_646 ?
N2 H2N 0.89(2) . ?
N3 Cu1 2.020(4) 2_655 ?
N4 H4N 0.880 . ?
O1 Cu1 1.961(3) . ?
O2 Cu1 2.342(4) 3_666 ?
O3 Cu1 1.967(3) . ?
Cu1 N3 2.020(4) 2_645 ?
Cu1 O2 2.342(4) 3_666 ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
O2 C1 O1 125.5(5) . . ?
O2 C1 C2 119.2(4) . . ?
O1 C1 C2 115.3(5) . . ?
C3 C2 C7 119.3(5) . . ?
C3 C2 C1 119.2(5) . . ?
C7 C2 C1 121.5(5) . . ?
C2 C3 C4 120.6(5) . . ?
C2 C3 H3 119.7 . . ?
C4 C3 H3 119.7 . . ?
C5 C4 C3 120.3(5) . . ?
C5 C4 H4 119.9 . . ?
C3 C4 H4 119.9 . . ?
C4 C5 C6 120.2(5) . . ?
C4 C5 C8 122.9(5) . . ?
C6 C5 C8 116.8(5) . . ?
C5 C6 C7 119.8(5) . . ?
C5 C6 H6 120.1 . . ?
C7 C6 H6 120.1 . . ?
C2 C7 C6 119.8(5) . . ?
C2 C7 H7 120.1 . . ?
C6 C7 H7 120.1 . . ?
O6 C8 N2 122.9(5) . . ?
O6 C8 C5 122.7(5) . . ?
N2 C8 C5 114.4(5) . . ?
N1 C9 C10 124.9(5) . . ?
N1 C9 H9 117.6 . . ?
C10 C9 H9 117.6 . . ?
C9 C10 C11 118.4(5) . . ?
C9 C10 H10 120.8 . . ?
C11 C10 H10 120.8 . . ?
N2 C11 C12 118.3(5) 2_656 . ?
N2 C11 C10 124.5(5) 2_656 . ?
C12 C11 C10 117.2(5) . . ?
C13 C12 C11 119.9(5) . . ?
C13 C12 H12 120.0 . . ?
C11 C12 H12 120.0 . . ?
N1 C13 C12 123.5(5) . . ?
N1 C13 H13 118.3 . . ?
C12 C13 H13 118.3 . . ?
O4 C14 O3 126.2(5) . . ?
O4 C14 C15 119.5(5) . . ?
O3 C14 C15 114.3(4) . . ?
C20 C15 C16 115.6(6) . . ?
C20 C15 C14 122.0(5) . . ?
C16 C15 C14 122.3(5) . . ?
C15 C16 C17 123.3(7) . . ?
C15 C16 H16 118.3 . . ?
C17 C16 H16 118.3 . . ?
C18 C17 C16 121.8(7) . . ?
C18 C17 H17 119.1 . . ?
C16 C17 H17 119.1 . . ?
C17 C18 C19 115.0(7) . . ?
C17 C18 C21 125.4(6) . . ?
C19 C18 C21 119.5(7) . . ?
C18 C19 C20 122.2(7) . . ?
C18 C19 H19 118.9 . . ?
C20 C19 H19 118.9 . . ?
C15 C20 C19 121.6(7) . . ?
C15 C20 H20 119.2 . . ?
C19 C20 H20 119.2 . . ?
O5 C21 N4 121.1(5) . . ?
O5 C21 C18 121.8(6) . . ?
N4 C21 C18 117.0(6) . . ?
C23 C22 N4 117.8(5) . . ?
C23 C22 C26 117.5(5) . . ?
N4 C22 C26 124.7(5) . . ?
C24 C23 C22 120.6(5) . . ?
C24 C23 H23 119.7 . . ?
C22 C23 H23 119.7 . . ?
N3 C24 C23 121.5(5) . . ?
N3 C24 H24 119.3 . . ?
C23 C24 H24 119.3 . . ?
N3 C25 C26 124.2(5) . . ?
N3 C25 H25 117.9 . . ?
C26 C25 H25 117.9 . . ?
C25 C26 C22 118.7(5) . . ?
C25 C26 H26 120.7 . . ?
C22 C26 H26 120.7 . . ?
N6 C27 H27A 109.5 . . ?
N6 C27 H27B 109.5 . . ?
H27A C27 H27B 109.5 . . ?
N6 C27 H27C 109.5 . . ?
H27A C27 H27C 109.5 . . ?
H27B C27 H27C 109.5 . . ?
N6 C28 H28A 109.5 . . ?
N6 C28 H28B 109.5 . . ?
H28A C28 H28B 109.5 . . ?
N6 C28 H28C 109.5 . . ?
H28A C28 H28C 109.5 . . ?
H28B C28 H28C 109.5 . . ?
O8 C29 N6 127.5(10) . . ?
O8 C29 H29 116.3 . . ?
N6 C29 H29 116.3 . . ?
C9 N1 C13 115.8(5) . . ?
C9 N1 Cu1 122.8(3) . . ?
C13 N1 Cu1 121.0(4) . . ?
C8 N2 C11 127.1(5) . 2_646 ?
C8 N2 H2N 122(4) . . ?
C11 N2 H2N 111(4) 2_646 . ?
C25 N3 C24 117.5(5) . . ?
C25 N3 Cu1 119.4(4) . 2_655 ?
C24 N3 Cu1 121.7(4) . 2_655 ?
C21 N4 C22 129.0(5) . . ?
C21 N4 H4N 115.00 . . ?
C22 N4 H4N 116.00 . . ?
C29 N6 C28 121.4(9) . . ?
C29 N6 C27 126.4(10) . . ?
C28 N6 C27 112.1(10) . . ?
C1 O1 Cu1 118.5(3) . . ?
C1 O2 Cu1 156.4(4) . 3_666 ?
C14 O3 Cu1 114.9(3) . . ?
O1 Cu1 O3 157.35(16) . . ?
O1 Cu1 N1 88.00(16) . . ?
O3 Cu1 N1 90.83(16) . . ?
O1 Cu1 N3 91.84(16) . 2_645 ?
O3 Cu1 N3 90.67(17) . 2_645 ?
N1 Cu1 N3 176.50(18) . 2_645 ?
O1 Cu1 O2 116.82(15) . 3_666 ?
O3 Cu1 O2 85.66(14) . 3_666 ?
N1 Cu1 O2 86.54(15) . 3_666 ?
N3 Cu1 O2 90.42(16) 2_645 3_666 ?

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
O2 C1 C2 C3 -8.8(8) . . . . ?
O1 C1 C2 C3 171.2(5) . . . . ?
O2 C1 C2 C7 171.6(5) . . . . ?
O1 C1 C2 C7 -8.4(7) . . . . ?
C7 C2 C3 C4 2.6(8) . . . . ?
C1 C2 C3 C4 -177.0(5) . . . . ?
C2 C3 C4 C5 -2.7(9) . . . . ?
C3 C4 C5 C6 2.1(9) . . . . ?
C3 C4 C5 C8 179.9(5) . . . . ?
C4 C5 C6 C7 -1.4(9) . . . . ?
C8 C5 C6 C7 -179.4(5) . . . . ?
C3 C2 C7 C6 -1.9(8) . . . . ?
C1 C2 C7 C6 177.7(5) . . . . ?
C5 C6 C7 C2 1.3(8) . . . . ?
C4 C5 C8 O6 -150.7(6) . . . . ?
C6 C5 C8 O6 27.2(9) . . . . ?
C4 C5 C8 N2 28.3(8) . . . . ?
C6 C5 C8 N2 -153.8(6) . . . . ?
N1 C9 C10 C11 -1.4(9) . . . . ?
C9 C10 C11 N2 176.4(6) . . . 2_656 ?
C9 C10 C11 C12 -3.4(9) . . . . ?
N2 C11 C12 C13 -175.9(5) 2_656 . . . ?
C10 C11 C12 C13 4.0(9) . . . . ?
C11 C12 C13 N1 0.2(9) . . . . ?
O4 C14 C15 C20 1.7(10) . . . . ?
O3 C14 C15 C20 -178.7(7) . . . . ?
O4 C14 C15 C16 176.9(7) . . . . ?
O3 C14 C15 C16 -3.4(9) . . . . ?
C20 C15 C16 C17 0.3(14) . . . . ?
C14 C15 C16 C17 -175.2(8) . . . . ?
C15 C16 C17 C18 -6.3(17) . . . . ?
C16 C17 C18 C19 6.2(16) . . . . ?
C16 C17 C18 C21 -178.2(9) . . . . ?
C17 C18 C19 C20 -0.7(16) . . . . ?
C21 C18 C19 C20 -176.6(9) . . . . ?
C16 C15 C20 C19 5.2(13) . . . . ?
C14 C15 C20 C19 -179.3(8) . . . . ?
C18 C19 C20 C15 -5.2(16) . . . . ?
C17 C18 C21 O5 166.5(10) . . . . ?
C19 C18 C21 O5 -18.1(14) . . . . ?
C17 C18 C21 N4 -12.0(14) . . . . ?
C19 C18 C21 N4 163.4(9) . . . . ?
N4 C22 C23 C24 -178.4(5) . . . . ?
C26 C22 C23 C24 3.6(9) . . . . ?
C22 C23 C24 N3 -2.5(9) . . . . ?
N3 C25 C26 C22 1.6(9) . . . . ?
C23 C22 C26 C25 -3.1(9) . . . . ?
N4 C22 C26 C25 179.1(6) . . . . ?
C10 C9 N1 C13 5.5(8) . . . . ?
C10 C9 N1 Cu1 -167.1(5) . . . . ?
C12 C13 N1 C9 -4.9(8) . . . . ?
C12 C13 N1 Cu1 167.9(4) . . . . ?
O6 C8 N2 C11 10.1(10) . . . 2_646 ?
C5 C8 N2 C11 -168.9(5) . . . 2_646 ?
C26 C25 N3 C24 -0.5(9) . . . . ?
C26 C25 N3 Cu1 -167.1(5) . . . 2_655 ?
C23 C24 N3 C25 0.9(8) . . . . ?
C23 C24 N3 Cu1 167.2(4) . . . 2_655 ?
O5 C21 N4 C22 2.8(11) . . . . ?
C18 C21 N4 C22 -178.7(7) . . . . ?
C23 C22 N4 C21 179.7(6) . . . . ?
C26 C22 N4 C21 -2.5(10) . . . . ?
O8 C29 N6 C28 4(2) . . . . ?
O8 C29 N6 C27 -171.8(14) . . . . ?
O2 C1 O1 Cu1 5.3(7) . . . . ?
C2 C1 O1 Cu1 -174.7(3) . . . . ?
O1 C1 O2 Cu1 -86.8(10) . . . 3_666 ?
C2 C1 O2 Cu1 93.3(9) . . . 3_666 ?
O4 C14 O3 Cu1 4.8(8) . . . . ?
C15 C14 O3 Cu1 -174.9(3) . . . . ?

_refine_diff_density_max         1.293
_refine_diff_density_min         -0.772
_refine_diff_density_rms         0.107

