# 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_Complex-4
_database_code_depnum_ccdc_archive 'CCDC 1402350'
_audit_update_record             
;
2015-06-22 deposited with the CCDC.
2015-09-21 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C14 H12 Cu N2 O6, C10 H8 N2'
_chemical_formula_sum            'C24 H20 Cu N4 O6'
_chemical_formula_weight         523.99

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

_cell_length_a                   10.6759(6)
_cell_length_b                   7.0765(4)
_cell_length_c                   14.7557(9)
_cell_angle_alpha                90.00
_cell_angle_beta                 96.369(4)
_cell_angle_gamma                90.00
_cell_volume                     1107.88(11)
_cell_formula_units_Z            2
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    ?
_cell_measurement_theta_min      ?
_cell_measurement_theta_max      ?

_exptl_crystal_description       Neddle
_exptl_crystal_colour            Black
_exptl_crystal_size_max          0.32
_exptl_crystal_size_mid          0.24
_exptl_crystal_size_min          0.12
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.571
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             538
_exptl_absorpt_coefficient_mu    1.037
_exptl_absorpt_correction_type   multi-Scan
_exptl_absorpt_correction_T_min  0.742
_exptl_absorpt_correction_T_max  0.883
_exptl_absorpt_process_details   multi-Scan

_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            16098
_diffrn_reflns_av_R_equivalents  0.0344
_diffrn_reflns_av_sigmaI/netI    0.0354
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_theta_min         1.39
_diffrn_reflns_theta_max         25.24
_reflns_number_total             3830
_reflns_number_gt                3231
_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 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)+(0.0000P)²+0.8000P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0.129(15)
_refine_ls_number_reflns         3830
_refine_ls_number_parameters     321
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0473
_refine_ls_R_factor_gt           0.0367
_refine_ls_wR_factor_ref         0.0713
_refine_ls_wR_factor_gt          0.0684
_refine_ls_goodness_of_fit_ref   1.086
_refine_ls_restrained_S_all      1.086
_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 0.08843(3) 0.55996(11) 0.90871(3) 0.04953(13) Uani 1 1 d . . .
O3 O 0.5283(2) 0.5368(7) 1.25358(15) 0.0677(9) Uani 1 1 d . . .
H3 H 0.5910 0.6018 1.2676 0.102 Uiso 1 1 calc R . .
O1 O 0.1871(2) 0.5067(4) 1.02224(15) 0.0527(10) Uani 1 1 d . . .
O5 O 0.2204(2) 0.6574(5) 0.75570(16) 0.0685(9) Uani 1 1 d . . .
H5 H 0.1454 0.6510 0.7364 0.103 Uiso 1 1 calc R . .
O2 O -0.0075(2) 0.6073(5) 0.79481(15) 0.0613(11) Uani 1 1 d . . .
O4 O -0.0429(2) 0.4192(5) 1.05464(16) 0.0586(7) Uani 1 1 d . . .
H4 H 0.0308 0.4354 1.0754 0.088 Uiso 1 1 calc R . .
O6 O -0.3483(2) 0.7017(5) 0.57195(18) 0.0740(9) Uani 1 1 d . . .
H6 H -0.4255 0.6987 0.5633 0.111 Uiso 1 1 calc R . .
N1 N 0.2353(3) 0.6237(4) 0.84961(19) 0.0517(10) Uani 1 1 d . . .
N2 N -0.0597(3) 0.4775(5) 0.9631(2) 0.0505(9) Uani 1 1 d . . .
C1 C 0.3482(3) 0.6515(6) 0.8880(2) 0.0477(10) Uani 1 1 d . . .
H1A H 0.4087 0.6924 0.8517 0.057 Uiso 1 1 calc R . .
C2 C 0.3862(3) 0.6231(5) 0.9830(2) 0.0457(11) Uani 1 1 d . . .
C3 C 0.5130(3) 0.6673(6) 1.0148(3) 0.0506(10) Uani 1 1 d . . .
H3A H 0.5652 0.7153 0.9739 0.061 Uiso 1 1 calc R . .
C4 C 0.5607(3) 0.6417(6) 1.1036(3) 0.0546(11) Uani 1 1 d . . .
H4A H 0.6440 0.6734 1.1227 0.065 Uiso 1 1 calc R . .
C5 C 0.4847(3) 0.5684(9) 1.1649(2) 0.0500(9) Uani 1 1 d . . .
C6 C 0.3591(3) 0.5212(6) 1.1367(2) 0.0479(12) Uani 1 1 d . . .
H6A H 0.3093 0.4702 1.1784 0.057 Uiso 1 1 calc R . .
C7 C 0.3077(3) 0.5500(10) 1.0462(2) 0.0445(8) Uani 1 1 d . . .
C8 C -0.1739(3) 0.4739(6) 0.9258(3) 0.0491(10) Uani 1 1 d . . .
H8 H -0.2352 0.4318 0.9611 0.059 Uiso 1 1 calc R . .
C9 C -0.2144(3) 0.5297(7) 0.8340(2) 0.0472(11) Uani 1 1 d . . .
C14 C -0.3442(3) 0.5188(6) 0.8023(3) 0.0526(13) Uani 1 1 d . . .
H14 H -0.3995 0.4725 0.8415 0.063 Uiso 1 1 calc R . .
C13 C -0.3914(3) 0.5732(9) 0.7172(2) 0.0572(10) Uani 1 1 d . . .
H13 H -0.4773 0.5635 0.6988 0.069 Uiso 1 1 calc R . .
C12 C -0.3102(3) 0.6441(6) 0.6571(3) 0.0547(11) Uani 1 1 d . . .
C11 C -0.1811(3) 0.6540(6) 0.6857(3) 0.0569(11) Uani 1 1 d . . .
H11 H -0.1269 0.7006 0.6458 0.068 Uiso 1 1 calc R . .
C10 C -0.1318(3) 0.5957(7) 0.7726(2) 0.0486(13) Uani 1 1 d . . .
N3 N 1.2258(3) 0.1625(6) 0.6985(2) 0.0710(11) Uani 1 1 d . . .
N4 N 0.5974(3) 0.2096(6) 0.4848(2) 0.0621(10) Uani 1 1 d . . .
C19 C 0.6220(4) 0.1699(7) 0.5714(3) 0.0758(15) Uani 1 1 d . . .
H19 H 0.5546 0.1417 0.6040 0.091 Uiso 1 1 calc R . .
C18 C 0.7426(4) 0.1672(7) 0.6177(3) 0.0737(14) Uani 1 1 d . . .
H18 H 0.7544 0.1379 0.6795 0.088 Uiso 1 1 calc R . .
C17 C 0.8446(3) 0.2083(6) 0.5715(2) 0.0471(9) Uani 1 1 d . . .
C16 C 0.8185(4) 0.2545(8) 0.4814(3) 0.0771(15) Uani 1 1 d . . .
H16 H 0.8836 0.2853 0.4472 0.093 Uiso 1 1 calc R . .
C15 C 0.6941(4) 0.2552(9) 0.4410(3) 0.0827(16) Uani 1 1 d . . .
H15 H 0.6786 0.2896 0.3800 0.099 Uiso 1 1 calc R . .
C20 C 0.9771(3) 0.1996(6) 0.6174(2) 0.0502(10) Uani 1 1 d . . .
C21 C 1.0779(4) 0.2633(8) 0.5747(3) 0.0750(14) Uani 1 1 d . . .
H21 H 1.0645 0.3207 0.5178 0.090 Uiso 1 1 calc R . .
C22 C 1.1999(4) 0.2408(9) 0.6177(3) 0.0859(16) Uani 1 1 d . . .
H22 H 1.2666 0.2834 0.5877 0.103 Uiso 1 1 calc R . .
C23 C 1.1301(4) 0.1046(8) 0.7402(3) 0.0781(18) Uani 1 1 d . . .
H23 H 1.1469 0.0499 0.7976 0.094 Uiso 1 1 calc R . .
C24 C 1.0045(4) 0.1212(7) 0.7027(3) 0.0718(17) Uani 1 1 d . . .
H24 H 0.9399 0.0796 0.7352 0.086 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 O2 1.898(2) . ?
Cu1 O1 1.915(2) . ?
Cu1 N1 1.930(3) . ?
Cu1 N2 1.941(3) . ?
O3 C5 1.358(4) . ?
O3 H3 0.8200 . ?
O1 C7 1.333(4) . ?
O5 N1 1.398(3) . ?
O5 H5 0.8200 . ?
O2 C10 1.334(4) . ?
O4 N2 1.405(4) . ?
O4 H4 0.8200 . ?
O6 C12 1.341(4) . ?
O6 H6 0.8200 . ?
N1 C1 1.289(4) . ?
N2 C8 1.281(4) . ?
C1 C2 1.430(5) . ?
C1 H1A 0.9300 . ?
C2 C3 1.418(5) . ?
C2 C7 1.419(5) . ?
C3 C4 1.363(5) . ?
C3 H3A 0.9300 . ?
C4 C5 1.382(5) . ?
C4 H4A 0.9300 . ?
C5 C6 1.399(5) . ?
C6 C7 1.400(4) . ?
C6 H6A 0.9300 . ?
C8 C9 1.430(5) . ?
C8 H8 0.9300 . ?
C9 C10 1.412(5) . ?
C9 C14 1.415(4) . ?
C14 C13 1.356(5) . ?
C14 H14 0.9300 . ?
C13 C12 1.399(5) . ?
C13 H13 0.9300 . ?
C12 C11 1.398(5) . ?
C11 C10 1.394(5) . ?
C11 H11 0.9300 . ?
N3 C23 1.315(5) . ?
N3 C22 1.316(5) . ?
N4 C19 1.306(5) . ?
N4 C15 1.318(5) . ?
C19 C18 1.389(5) . ?
C19 H19 0.9300 . ?
C18 C17 1.378(5) . ?
C18 H18 0.9300 . ?
C17 C16 1.368(5) . ?
C17 C20 1.500(5) . ?
C16 C15 1.394(5) . ?
C16 H16 0.9300 . ?
C15 H15 0.9300 . ?
C20 C24 1.378(5) . ?
C20 C21 1.381(5) . ?
C21 C22 1.393(5) . ?
C21 H21 0.9300 . ?
C22 H22 0.9300 . ?
C23 C24 1.398(5) . ?
C23 H23 0.9300 . ?
C24 H24 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
O2 Cu1 O1 178.52(14) . . ?
O2 Cu1 N1 86.79(11) . . ?
O1 Cu1 N1 92.63(10) . . ?
O2 Cu1 N2 92.00(11) . . ?
O1 Cu1 N2 88.48(11) . . ?
N1 Cu1 N2 175.58(15) . . ?
C5 O3 H3 109.5 . . ?
C7 O1 Cu1 127.5(2) . . ?
N1 O5 H5 109.5 . . ?
C10 O2 Cu1 129.1(2) . . ?
N2 O4 H4 109.5 . . ?
C12 O6 H6 109.5 . . ?
C1 N1 O5 114.1(3) . . ?
C1 N1 Cu1 127.2(3) . . ?
O5 N1 Cu1 118.63(19) . . ?
C8 N2 O4 115.0(3) . . ?
C8 N2 Cu1 127.5(3) . . ?
O4 N2 Cu1 117.6(2) . . ?
N1 C1 C2 124.0(3) . . ?
N1 C1 H1A 118.0 . . ?
C2 C1 H1A 118.0 . . ?
C3 C2 C7 118.3(3) . . ?
C3 C2 C1 116.8(3) . . ?
C7 C2 C1 124.9(3) . . ?
C4 C3 C2 122.0(4) . . ?
C4 C3 H3A 119.0 . . ?
C2 C3 H3A 119.0 . . ?
C3 C4 C5 119.6(3) . . ?
C3 C4 H4A 120.2 . . ?
C5 C4 H4A 120.2 . . ?
O3 C5 C4 121.9(3) . . ?
O3 C5 C6 117.5(4) . . ?
C4 C5 C6 120.5(3) . . ?
C5 C6 C7 120.6(4) . . ?
C5 C6 H6A 119.7 . . ?
C7 C6 H6A 119.7 . . ?
O1 C7 C6 119.0(3) . . ?
O1 C7 C2 122.2(3) . . ?
C6 C7 C2 118.8(3) . . ?
N2 C8 C9 125.1(3) . . ?
N2 C8 H8 117.5 . . ?
C9 C8 H8 117.5 . . ?
C10 C9 C14 117.7(3) . . ?
C10 C9 C8 123.7(3) . . ?
C14 C9 C8 118.7(3) . . ?
C13 C14 C9 122.7(4) . . ?
C13 C14 H14 118.7 . . ?
C9 C14 H14 118.7 . . ?
C14 C13 C12 119.8(3) . . ?
C14 C13 H13 120.1 . . ?
C12 C13 H13 120.1 . . ?
O6 C12 C11 117.0(4) . . ?
O6 C12 C13 123.9(3) . . ?
C11 C12 C13 119.1(3) . . ?
C10 C11 C12 121.4(4) . . ?
C10 C11 H11 119.3 . . ?
C12 C11 H11 119.3 . . ?
O2 C10 C11 118.1(3) . . ?
O2 C10 C9 122.5(3) . . ?
C11 C10 C9 119.3(3) . . ?
C23 N3 C22 117.3(4) . . ?
C19 N4 C15 116.7(3) . . ?
N4 C19 C18 123.9(4) . . ?
N4 C19 H19 118.0 . . ?
C18 C19 H19 118.0 . . ?
C17 C18 C19 119.7(4) . . ?
C17 C18 H18 120.2 . . ?
C19 C18 H18 120.2 . . ?
C16 C17 C18 116.3(4) . . ?
C16 C17 C20 121.9(4) . . ?
C18 C17 C20 121.8(3) . . ?
C17 C16 C15 119.9(4) . . ?
C17 C16 H16 120.0 . . ?
C15 C16 H16 120.0 . . ?
N4 C15 C16 123.4(4) . . ?
N4 C15 H15 118.3 . . ?
C16 C15 H15 118.3 . . ?
C24 C20 C21 116.8(3) . . ?
C24 C20 C17 121.5(4) . . ?
C21 C20 C17 121.7(3) . . ?
C20 C21 C22 119.5(4) . . ?
C20 C21 H21 120.3 . . ?
C22 C21 H21 120.3 . . ?
N3 C22 C21 123.5(4) . . ?
N3 C22 H22 118.2 . . ?
C21 C22 H22 118.2 . . ?
N3 C23 C24 123.4(4) . . ?
N3 C23 H23 118.3 . . ?
C24 C23 H23 118.3 . . ?
C20 C24 C23 119.5(4) . . ?
C20 C24 H24 120.3 . . ?
C23 C24 H24 120.3 . . ?

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 Cu1 O1 C7 80(5) . . . . ?
N1 Cu1 O1 C7 13.5(4) . . . . ?
N2 Cu1 O1 C7 -170.8(4) . . . . ?
O1 Cu1 O2 C10 113(5) . . . . ?
N1 Cu1 O2 C10 -179.9(4) . . . . ?
N2 Cu1 O2 C10 4.3(4) . . . . ?
O2 Cu1 N1 C1 169.5(4) . . . . ?
O1 Cu1 N1 C1 -11.9(3) . . . . ?
N2 Cu1 N1 C1 -116.3(16) . . . . ?
O2 Cu1 N1 O5 -5.7(3) . . . . ?
O1 Cu1 N1 O5 172.9(3) . . . . ?
N2 Cu1 N1 O5 68.5(18) . . . . ?
O2 Cu1 N2 C8 -2.4(4) . . . . ?
O1 Cu1 N2 C8 179.0(4) . . . . ?
N1 Cu1 N2 C8 -76.4(18) . . . . ?
O2 Cu1 N2 O4 179.5(3) . . . . ?
O1 Cu1 N2 O4 0.9(3) . . . . ?
N1 Cu1 N2 O4 105.5(17) . . . . ?
O5 N1 C1 C2 -179.0(3) . . . . ?
Cu1 N1 C1 C2 5.6(6) . . . . ?
N1 C1 C2 C3 -177.6(4) . . . . ?
N1 C1 C2 C7 4.2(7) . . . . ?
C7 C2 C3 C4 0.0(6) . . . . ?
C1 C2 C3 C4 -178.4(4) . . . . ?
C2 C3 C4 C5 0.8(6) . . . . ?
C3 C4 C5 O3 178.7(5) . . . . ?
C3 C4 C5 C6 -0.3(8) . . . . ?
O3 C5 C6 C7 180.0(5) . . . . ?
C4 C5 C6 C7 -1.0(9) . . . . ?
Cu1 O1 C7 C6 171.7(3) . . . . ?
Cu1 O1 C7 C2 -8.8(8) . . . . ?
C5 C6 C7 O1 -178.7(5) . . . . ?
C5 C6 C7 C2 1.7(8) . . . . ?
C3 C2 C7 O1 179.3(5) . . . . ?
C1 C2 C7 O1 -2.5(8) . . . . ?
C3 C2 C7 C6 -1.2(7) . . . . ?
C1 C2 C7 C6 177.0(4) . . . . ?
O4 N2 C8 C9 178.9(4) . . . . ?
Cu1 N2 C8 C9 0.8(6) . . . . ?
N2 C8 C9 C10 0.2(8) . . . . ?
N2 C8 C9 C14 -179.7(4) . . . . ?
C10 C9 C14 C13 -1.7(8) . . . . ?
C8 C9 C14 C13 178.3(5) . . . . ?
C9 C14 C13 C12 -0.2(8) . . . . ?
C14 C13 C12 O6 -179.8(5) . . . . ?
C14 C13 C12 C11 1.2(8) . . . . ?
O6 C12 C11 C10 -179.3(4) . . . . ?
C13 C12 C11 C10 -0.2(7) . . . . ?
Cu1 O2 C10 C11 174.5(3) . . . . ?
Cu1 O2 C10 C9 -4.6(7) . . . . ?
C12 C11 C10 O2 179.3(4) . . . . ?
C12 C11 C10 C9 -1.7(7) . . . . ?
C14 C9 C10 O2 -178.4(4) . . . . ?
C8 C9 C10 O2 1.6(8) . . . . ?
C14 C9 C10 C11 2.6(7) . . . . ?
C8 C9 C10 C11 -177.4(4) . . . . ?
C15 N4 C19 C18 -2.2(8) . . . . ?
N4 C19 C18 C17 0.0(8) . . . . ?
C19 C18 C17 C16 1.6(7) . . . . ?
C19 C18 C17 C20 -177.4(4) . . . . ?
C18 C17 C16 C15 -1.0(8) . . . . ?
C20 C17 C16 C15 178.1(5) . . . . ?
C19 N4 C15 C16 2.9(8) . . . . ?
C17 C16 C15 N4 -1.3(9) . . . . ?
C16 C17 C20 C24 -168.2(5) . . . . ?
C18 C17 C20 C24 10.7(7) . . . . ?
C16 C17 C20 C21 9.3(7) . . . . ?
C18 C17 C20 C21 -171.7(5) . . . . ?
C24 C20 C21 C22 1.9(7) . . . . ?
C17 C20 C21 C22 -175.8(5) . . . . ?
C23 N3 C22 C21 -0.6(9) . . . . ?
C20 C21 C22 N3 -0.6(9) . . . . ?
C22 N3 C23 C24 0.5(8) . . . . ?
C21 C20 C24 C23 -1.9(7) . . . . ?
C17 C20 C24 C23 175.7(4) . . . . ?
N3 C23 C24 C20 0.8(8) . . . . ?

_diffrn_measured_fraction_theta_max 0.995
_diffrn_reflns_theta_full        25.24
_diffrn_measured_fraction_theta_full 0.995
_refine_diff_density_max         0.441
_refine_diff_density_min         -0.284
_refine_diff_density_rms         0.048
####################################################################### 
# 
# 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_complex-1
_database_code_depnum_ccdc_archive 'CCDC 1402351'
_audit_update_record             
;
2015-06-22 deposited with the CCDC.
2015-09-21 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C14 H12 Cu N2 O6, 2(C3 H7 N O)'
_chemical_formula_sum            'C20 H26 Cu N4 O8'
_chemical_formula_weight         514.00

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                   6.1974(7)
_cell_length_b                   7.3044(9)
_cell_length_c                   13.1416(16)
_cell_angle_alpha                91.394(5)
_cell_angle_beta                 102.247(5)
_cell_angle_gamma                101.071(5)
_cell_volume                     569.23(12)
_cell_formula_units_Z            1
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    ?
_cell_measurement_theta_min      ?
_cell_measurement_theta_max      ?

_exptl_crystal_description       Block
_exptl_crystal_colour            Black
_exptl_crystal_size_max          0.32
_exptl_crystal_size_mid          0.23
_exptl_crystal_size_min          0.11
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.499
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             267
_exptl_absorpt_coefficient_mu    1.013
_exptl_absorpt_correction_type   multi-Scan
_exptl_absorpt_correction_T_min  0.756
_exptl_absorpt_correction_T_max  0.895
_exptl_absorpt_process_details   multi-Scan

_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            2613
_diffrn_reflns_av_R_equivalents  0.0170
_diffrn_reflns_av_sigmaI/netI    0.0230
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_k_max       6
_diffrn_reflns_limit_l_min       -10
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_theta_min         1.59
_diffrn_reflns_theta_max         25.24
_reflns_number_total             2040
_reflns_number_gt                1279
_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 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)+(0.1000P)²+0.1000P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         2040
_refine_ls_number_parameters     155
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0407
_refine_ls_R_factor_gt           0.0387
_refine_ls_wR_factor_ref         0.1222
_refine_ls_wR_factor_gt          0.1184
_refine_ls_goodness_of_fit_ref   1.034
_refine_ls_restrained_S_all      1.034
_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 1.0000 0.0000 0.0000 0.0364(4) Uani 1 2 d S . .
O2 O 0.8191(5) -0.3947(4) -0.0033(2) 0.0493(9) Uani 1 1 d . . .
H2 H 0.9192 -0.3829 -0.0361 0.074 Uiso 1 1 calc R . .
O3 O 0.4233(6) 0.3931(5) 0.2698(3) 0.0633(10) Uani 1 1 d . . .
H3 H 0.3339 0.3577 0.3067 0.095 Uiso 1 1 calc R . .
O1 O 0.8842(4) 0.1642(4) 0.0782(2) 0.0401(8) Uani 1 1 d . . .
N1 N 0.8032(5) -0.2193(4) 0.0348(2) 0.0355(9) Uani 1 1 d . . .
C1 C 0.6413(6) -0.2209(6) 0.0833(3) 0.0385(13) Uani 1 1 d . . .
H1A H 0.5497 -0.3359 0.0878 0.046 Uiso 1 1 calc R . .
C2 C 0.5931(6) -0.0604(5) 0.1303(3) 0.0329(12) Uani 1 1 d . . .
C3 C 0.4131(6) -0.0845(7) 0.1811(3) 0.0443(14) Uani 1 1 d . . .
H3A H 0.3322 -0.2048 0.1838 0.053 Uiso 1 1 calc R . .
C4 C 0.3519(7) 0.0611(7) 0.2266(3) 0.0465(13) Uani 1 1 d . . .
H4 H 0.2299 0.0401 0.2585 0.056 Uiso 1 1 calc R . .
C5 C 0.4742(7) 0.2427(7) 0.2249(3) 0.0419(13) Uani 1 1 d . . .
C6 C 0.6511(6) 0.2726(6) 0.1750(3) 0.0402(13) Uani 1 1 d . . .
H6 H 0.7301 0.3940 0.1735 0.048 Uiso 1 1 calc R . .
C7 C 0.7143(6) 0.1268(6) 0.1271(3) 0.0356(13) Uani 1 1 d . . .
O4 O -0.1981(9) 0.7079(7) 0.5789(4) 0.1056(15) Uani 1 1 d . . .
N2 N 0.0331(6) 0.7482(5) 0.4690(3) 0.0569(12) Uani 1 1 d . . .
C10 C -0.0169(12) 0.7304(9) 0.5618(5) 0.088(2) Uani 1 1 d . . .
H10 H 0.1029 0.7363 0.6188 0.106 Uiso 1 1 calc R . .
C9 C -0.1234(11) 0.7489(9) 0.3746(4) 0.110(3) Uani 1 1 d . . .
H9A H -0.2732 0.7053 0.3846 0.165 Uiso 1 1 calc R . .
H9B H -0.0942 0.6682 0.3226 0.165 Uiso 1 1 calc R . .
H9C H -0.1096 0.8738 0.3520 0.165 Uiso 1 1 calc R . .
C8 C 0.2700(10) 0.7821(10) 0.4665(6) 0.117(3) Uani 1 1 d . . .
H8A H 0.3116 0.9014 0.4393 0.176 Uiso 1 1 calc R . .
H8B H 0.2970 0.6857 0.4227 0.176 Uiso 1 1 calc R . .
H8C H 0.3586 0.7816 0.5359 0.176 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 1.895(3) 2_755 ?
Cu1 O1 1.895(3) . ?
Cu1 N1 1.945(3) . ?
Cu1 N1 1.945(3) 2_755 ?
O2 N1 1.393(4) . ?
O2 H2 0.8200 . ?
O3 C5 1.355(5) . ?
O3 H3 0.8200 . ?
O1 C7 1.335(4) . ?
N1 C1 1.296(5) . ?
C1 C2 1.422(6) . ?
C1 H1A 0.9300 . ?
C2 C3 1.402(6) . ?
C2 C7 1.435(5) . ?
C3 C4 1.361(6) . ?
C3 H3A 0.9300 . ?
C4 C5 1.398(6) . ?
C4 H4 0.9300 . ?
C5 C6 1.378(6) . ?
C6 C7 1.384(6) . ?
C6 H6 0.9300 . ?
O4 C10 1.173(8) . ?
N2 C10 1.323(8) . ?
N2 C9 1.404(6) . ?
N2 C8 1.449(7) . ?
C10 H10 0.9300 . ?
C9 H9A 0.9600 . ?
C9 H9B 0.9600 . ?
C9 H9C 0.9600 . ?
C8 H8A 0.9600 . ?
C8 H8B 0.9600 . ?
C8 H8C 0.9600 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
O1 Cu1 O1 180.0 2_755 . ?
O1 Cu1 N1 87.60(13) 2_755 . ?
O1 Cu1 N1 92.40(13) . . ?
O1 Cu1 N1 92.40(13) 2_755 2_755 ?
O1 Cu1 N1 87.60(13) . 2_755 ?
N1 Cu1 N1 180.0 . 2_755 ?
N1 O2 H2 109.5 . . ?
C5 O3 H3 109.5 . . ?
C7 O1 Cu1 129.5(3) . . ?
C1 N1 O2 114.5(3) . . ?
C1 N1 Cu1 126.8(3) . . ?
O2 N1 Cu1 118.4(2) . . ?
N1 C1 C2 125.1(3) . . ?
N1 C1 H1A 117.5 . . ?
C2 C1 H1A 117.5 . . ?
C3 C2 C1 118.5(4) . . ?
C3 C2 C7 117.4(4) . . ?
C1 C2 C7 124.0(4) . . ?
C4 C3 C2 122.7(4) . . ?
C4 C3 H3A 118.7 . . ?
C2 C3 H3A 118.7 . . ?
C3 C4 C5 119.4(4) . . ?
C3 C4 H4 120.3 . . ?
C5 C4 H4 120.3 . . ?
O3 C5 C6 118.0(4) . . ?
O3 C5 C4 122.2(4) . . ?
C6 C5 C4 119.7(5) . . ?
C5 C6 C7 121.8(4) . . ?
C5 C6 H6 119.1 . . ?
C7 C6 H6 119.1 . . ?
O1 C7 C6 119.3(3) . . ?
O1 C7 C2 121.8(4) . . ?
C6 C7 C2 118.9(4) . . ?
C10 N2 C9 125.2(5) . . ?
C10 N2 C8 116.8(5) . . ?
C9 N2 C8 117.8(5) . . ?
O4 C10 N2 126.2(6) . . ?
O4 C10 H10 116.9 . . ?
N2 C10 H10 116.9 . . ?
N2 C9 H9A 109.5 . . ?
N2 C9 H9B 109.5 . . ?
H9A C9 H9B 109.5 . . ?
N2 C9 H9C 109.5 . . ?
H9A C9 H9C 109.5 . . ?
H9B C9 H9C 109.5 . . ?
N2 C8 H8A 109.5 . . ?
N2 C8 H8B 109.5 . . ?
H8A C8 H8B 109.5 . . ?
N2 C8 H8C 109.5 . . ?
H8A C8 H8C 109.5 . . ?
H8B C8 H8C 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
O1 Cu1 O1 C7 -90(12) 2_755 . . . ?
N1 Cu1 O1 C7 -5.4(3) . . . . ?
N1 Cu1 O1 C7 174.6(3) 2_755 . . . ?
O1 Cu1 N1 C1 -172.5(3) 2_755 . . . ?
O1 Cu1 N1 C1 7.5(3) . . . . ?
N1 Cu1 N1 C1 -49(4) 2_755 . . . ?
O1 Cu1 N1 O2 1.2(2) 2_755 . . . ?
O1 Cu1 N1 O2 -178.8(2) . . . . ?
N1 Cu1 N1 O2 125(3) 2_755 . . . ?
O2 N1 C1 C2 179.0(3) . . . . ?
Cu1 N1 C1 C2 -7.1(5) . . . . ?
N1 C1 C2 C3 -179.5(3) . . . . ?
N1 C1 C2 C7 2.1(5) . . . . ?
C1 C2 C3 C4 -178.8(3) . . . . ?
C7 C2 C3 C4 -0.2(5) . . . . ?
C2 C3 C4 C5 -1.1(6) . . . . ?
C3 C4 C5 O3 -179.2(4) . . . . ?
C3 C4 C5 C6 1.7(5) . . . . ?
O3 C5 C6 C7 180.0(3) . . . . ?
C4 C5 C6 C7 -0.9(6) . . . . ?
Cu1 O1 C7 C6 -176.4(2) . . . . ?
Cu1 O1 C7 C2 2.7(5) . . . . ?
C5 C6 C7 O1 178.7(3) . . . . ?
C5 C6 C7 C2 -0.5(5) . . . . ?
C3 C2 C7 O1 -178.2(3) . . . . ?
C1 C2 C7 O1 0.3(5) . . . . ?
C3 C2 C7 C6 1.0(5) . . . . ?
C1 C2 C7 C6 179.5(3) . . . . ?
C9 N2 C10 O4 2.1(11) . . . . ?
C8 N2 C10 O4 177.7(7) . . . . ?

_diffrn_measured_fraction_theta_max 0.987
_diffrn_reflns_theta_full        25.24
_diffrn_measured_fraction_theta_full 0.987
_refine_diff_density_max         0.513
_refine_diff_density_min         -0.306
_refine_diff_density_rms         0.073
####################################################################### 
# 
# 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_Complex-3
_database_code_depnum_ccdc_archive 'CCDC 1402352'
_audit_update_record             
;
2015-06-22 deposited with the CCDC.
2015-09-21 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C14 H12 Cu N2 O6, C2 H6 O S'
_chemical_formula_sum            'C16 H18 Cu N2 O7 S'
_chemical_formula_weight         445.93

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'
S S 0.1246 0.1234 '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                   8.3981(7)
_cell_length_b                   9.6705(9)
_cell_length_c                   12.5186(9)
_cell_angle_alpha                73.944(7)
_cell_angle_beta                 86.252(6)
_cell_angle_gamma                67.507(9)
_cell_volume                     901.77(13)
_cell_formula_units_Z            2
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    ?
_cell_measurement_theta_min      ?
_cell_measurement_theta_max      ?

_exptl_crystal_description       Block
_exptl_crystal_colour            Black
_exptl_crystal_size_max          0.32
_exptl_crystal_size_mid          0.24
_exptl_crystal_size_min          0.12
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.642
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             458
_exptl_absorpt_coefficient_mu    1.369
_exptl_absorpt_correction_type   multi-Scan
_exptl_absorpt_correction_T_min  0.681
_exptl_absorpt_correction_T_max  0.849
_exptl_absorpt_process_details   multi-Scan

_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            5639
_diffrn_reflns_av_R_equivalents  0.0290
_diffrn_reflns_av_sigmaI/netI    0.0601
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_theta_min         2.98
_diffrn_reflns_theta_max         25.25
_reflns_number_total             3252
_reflns_number_gt                2383
_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 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)+(0.0100P)²+0.7600P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         3252
_refine_ls_number_parameters     250
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0651
_refine_ls_R_factor_gt           0.0430
_refine_ls_wR_factor_ref         0.0852
_refine_ls_wR_factor_gt          0.0734
_refine_ls_goodness_of_fit_ref   1.027
_refine_ls_restrained_S_all      1.027
_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
Cu Cu 0.75991(6) 0.92769(5) 0.10237(3) 0.03936(16) Uani 1 1 d . . .
S1 S 0.26774(15) 0.03356(12) 0.35063(8) 0.0521(3) Uani 1 1 d . . .
O3 O 0.8111(4) 1.4878(3) -0.3195(2) 0.0551(8) Uani 1 1 d . . .
H3 H 0.7870 1.4440 -0.3598 0.083 Uiso 1 1 calc R . .
O7 O 0.3367(4) -0.1183(3) 0.4387(2) 0.0755(10) Uani 1 1 d . . .
O6 O 0.7327(4) 0.3679(3) 0.5265(2) 0.0603(9) Uani 1 1 d . . .
H6 H 0.7130 0.2886 0.5359 0.091 Uiso 1 1 calc R . .
O1 O 0.7605(3) 1.0621(3) -0.04130(18) 0.0427(7) Uani 1 1 d . . .
C9 C 0.6636(5) 0.6159(4) 0.1931(3) 0.0366(9) Uani 1 1 d . . .
C3 C 0.7989(4) 1.1874(4) -0.0674(3) 0.0331(8) Uani 1 1 d . . .
N2 N 0.6715(4) 0.8161(3) 0.0313(2) 0.0425(8) Uani 1 1 d . . .
N1 N 0.8465(4) 1.0400(3) 0.1747(2) 0.0391(8) Uani 1 1 d . . .
C14 C 0.7233(5) 0.6673(4) 0.2722(3) 0.0369(9) Uani 1 1 d . . .
C2 C 0.8525(4) 1.2412(4) 0.0123(3) 0.0347(9) Uani 1 1 d . . .
O5 O 0.8838(4) 0.9832(3) 0.28911(19) 0.0533(8) Uani 1 1 d . . .
H5 H 0.8716 0.8999 0.3121 0.080 Uiso 1 1 calc R . .
C10 C 0.6277(5) 0.4806(4) 0.2302(3) 0.0423(10) Uani 1 1 d . . .
H10 H 0.5878 0.4470 0.1785 0.051 Uiso 1 1 calc R . .
O2 O 0.7573(3) 0.7954(3) 0.24537(19) 0.0464(7) Uani 1 1 d . . .
C4 C 0.7881(5) 1.2709(4) -0.1794(3) 0.0372(9) Uani 1 1 d . . .
H4 H 0.7572 1.2348 -0.2333 0.045 Uiso 1 1 calc R . .
C5 C 0.8218(5) 1.4040(4) -0.2121(3) 0.0398(9) Uani 1 1 d . . .
C12 C 0.7080(5) 0.4471(4) 0.4163(3) 0.0427(10) Uani 1 1 d . . .
C1 C 0.8775(5) 1.1621(4) 0.1287(3) 0.0395(9) Uani 1 1 d . . .
H1A H 0.9197 1.2028 0.1744 0.047 Uiso 1 1 calc R . .
C13 C 0.7438(5) 0.5800(4) 0.3835(3) 0.0451(10) Uani 1 1 d . . .
H13 H 0.7824 0.6124 0.4366 0.054 Uiso 1 1 calc R . .
O4 O 0.6321(4) 0.8741(3) -0.0836(2) 0.0615(9) Uani 1 1 d . . .
H4A H 0.6733 0.9400 -0.1101 0.092 Uiso 1 1 calc R . .
C8 C 0.6363(5) 0.6960(4) 0.0763(3) 0.0412(9) Uani 1 1 d . . .
H8 H 0.5901 0.6579 0.0308 0.049 Uiso 1 1 calc R . .
C11 C 0.6492(5) 0.3956(4) 0.3397(3) 0.0436(10) Uani 1 1 d . . .
H11 H 0.6251 0.3059 0.3620 0.052 Uiso 1 1 calc R . .
C6 C 0.8718(5) 1.4587(4) -0.1334(3) 0.0500(11) Uani 1 1 d . . .
H6A H 0.8949 1.5489 -0.1550 0.060 Uiso 1 1 calc R . .
C7 C 0.8861(5) 1.3776(4) -0.0242(3) 0.0479(11) Uani 1 1 d . . .
H7 H 0.9195 1.4143 0.0283 0.057 Uiso 1 1 calc R . .
C16 C 0.1118(6) 0.1623(5) 0.4152(4) 0.0892(17) Uani 1 1 d . . .
H16A H 0.0143 0.1324 0.4304 0.134 Uiso 1 1 calc R . .
H16B H 0.0756 0.2661 0.3667 0.134 Uiso 1 1 calc R . .
H16C H 0.1605 0.1588 0.4836 0.134 Uiso 1 1 calc R . .
C15 C 0.4280(5) 0.1128(5) 0.3387(3) 0.0613(12) Uani 1 1 d . . .
H15A H 0.4528 0.1204 0.4101 0.092 Uiso 1 1 calc R . .
H15B H 0.3873 0.2145 0.2870 0.092 Uiso 1 1 calc R . .
H15C H 0.5309 0.0466 0.3124 0.092 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
Cu O2 1.895(2) . ?
Cu O1 1.907(2) . ?
Cu N2 1.934(3) . ?
Cu N1 1.940(3) . ?
S1 O7 1.498(3) . ?
S1 C16 1.757(5) . ?
S1 C15 1.766(4) . ?
O3 C5 1.353(4) . ?
O6 C12 1.365(4) . ?
O1 C3 1.321(4) . ?
C9 C10 1.403(5) . ?
C9 C14 1.416(5) . ?
C9 C8 1.439(5) . ?
C3 C4 1.401(4) . ?
C3 C2 1.412(5) . ?
N2 C8 1.278(4) . ?
N2 O4 1.403(3) . ?
N1 C1 1.278(4) . ?
N1 O5 1.394(3) . ?
C14 O2 1.326(4) . ?
C14 C13 1.398(4) . ?
C2 C7 1.401(5) . ?
C2 C1 1.433(4) . ?
C10 C11 1.372(5) . ?
C4 C5 1.371(5) . ?
C5 C6 1.392(5) . ?
C12 C13 1.378(5) . ?
C12 C11 1.388(5) . ?
C6 C7 1.362(5) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
O2 Cu O1 179.48(12) . . ?
O2 Cu N2 92.01(11) . . ?
O1 Cu N2 88.05(11) . . ?
O2 Cu N1 87.61(11) . . ?
O1 Cu N1 92.32(11) . . ?
N2 Cu N1 179.37(13) . . ?
O7 S1 C16 105.4(2) . . ?
O7 S1 C15 105.60(19) . . ?
C16 S1 C15 98.7(2) . . ?
C3 O1 Cu 128.5(2) . . ?
C10 C9 C14 118.5(3) . . ?
C10 C9 C8 118.0(3) . . ?
C14 C9 C8 123.5(3) . . ?
O1 C3 C4 118.9(3) . . ?
O1 C3 C2 123.2(3) . . ?
C4 C3 C2 117.9(3) . . ?
C8 N2 O4 113.5(3) . . ?
C8 N2 Cu 128.3(3) . . ?
O4 N2 Cu 118.1(2) . . ?
C1 N1 O5 114.5(3) . . ?
C1 N1 Cu 127.2(2) . . ?
O5 N1 Cu 118.3(2) . . ?
O2 C14 C13 118.9(3) . . ?
O2 C14 C9 122.9(3) . . ?
C13 C14 C9 118.2(3) . . ?
C7 C2 C3 118.5(3) . . ?
C7 C2 C1 118.0(3) . . ?
C3 C2 C1 123.5(3) . . ?
C11 C10 C9 122.7(3) . . ?
C14 O2 Cu 128.8(2) . . ?
C5 C4 C3 121.9(3) . . ?
O3 C5 C4 123.3(3) . . ?
O3 C5 C6 116.5(3) . . ?
C4 C5 C6 120.2(3) . . ?
O6 C12 C13 117.8(3) . . ?
O6 C12 C11 121.2(3) . . ?
C13 C12 C11 121.0(3) . . ?
N1 C1 C2 125.1(3) . . ?
C12 C13 C14 121.4(3) . . ?
N2 C8 C9 124.1(3) . . ?
C10 C11 C12 118.2(3) . . ?
C7 C6 C5 118.8(3) . . ?
C6 C7 C2 122.6(3) . . ?

_diffrn_measured_fraction_theta_max 0.998
_diffrn_reflns_theta_full        25.25
_diffrn_measured_fraction_theta_full 0.998
_refine_diff_density_max         0.331
_refine_diff_density_min         -0.403
_refine_diff_density_rms         0.067
####################################################################### 
# 
# 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_Complex-6
_database_code_depnum_ccdc_archive 'CCDC 1402353'
_audit_update_record             
;
2015-06-22 deposited with the CCDC.
2015-09-21 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C14 H12 N2 Ni O6'
_chemical_formula_sum            'C14 H12 N2 Ni O6'
_chemical_formula_weight         362.95

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'
Ni Ni 0.3393 1.1124 '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                   6.8784(8)
_cell_length_b                   7.0931(8)
_cell_length_c                   27.221(3)
_cell_angle_alpha                90.00
_cell_angle_beta                 90.610(3)
_cell_angle_gamma                90.00
_cell_volume                     1328.0(3)
_cell_formula_units_Z            4
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    ?
_cell_measurement_theta_min      ?
_cell_measurement_theta_max      ?

_exptl_crystal_description       Neddle
_exptl_crystal_colour            Blue
_exptl_crystal_size_max          0.32
_exptl_crystal_size_mid          0.24
_exptl_crystal_size_min          0.12
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.815
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             744
_exptl_absorpt_coefficient_mu    1.498
_exptl_absorpt_correction_type   multi-Scan
_exptl_absorpt_correction_T_min  0.656
_exptl_absorpt_correction_T_max  0.835
_exptl_absorpt_process_details   multi-Scan

_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            4200
_diffrn_reflns_av_R_equivalents  0.0273
_diffrn_reflns_av_sigmaI/netI    0.0551
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_h_max       5
_diffrn_reflns_limit_k_min       -4
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_l_min       -31
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_theta_min         1.50
_diffrn_reflns_theta_max         25.24
_reflns_number_total             2390
_reflns_number_gt                1239
_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 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)+(0.1100P)²+6.0000P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         2390
_refine_ls_number_parameters     209
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0887
_refine_ls_R_factor_gt           0.0658
_refine_ls_wR_factor_ref         0.2031
_refine_ls_wR_factor_gt          0.1902
_refine_ls_goodness_of_fit_ref   1.077
_refine_ls_restrained_S_all      1.077
_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
O5 O 0.4413(8) 0.3216(11) 0.0485(2) 0.0415(19) Uani 1 1 d . . .
H5 H 0.4385 0.3330 0.0785 0.062 Uiso 1 1 calc R . .
Ni1 Ni 0.07026(17) 0.18516(17) 0.07408(4) 0.0322(5) Uani 1 1 d . . .
O3 O -0.4529(9) 0.2484(9) -0.1251(2) 0.0392(18) Uani 1 1 d . . .
H3A H -0.5178 0.1548 -0.1187 0.059 Uiso 1 1 d R . .
O1 O -0.1198(9) 0.1684(9) 0.02659(19) 0.0370(17) Uani 1 1 d . . .
O4 O -0.3005(8) 0.0481(10) 0.09973(19) 0.0433(19) Uani 1 1 d . . .
H4A H -0.3032 0.0687 0.0701 0.065 Uiso 1 1 d R . .
O6 O 0.5750(10) 0.2152(12) 0.2737(2) 0.059(2) Uani 1 1 d . . .
H5A H 0.5605 0.2060 0.3035 0.088 Uiso 1 1 d R . .
O2 O 0.2604(9) 0.1981(9) 0.12142(19) 0.0383(18) Uani 1 1 d . . .
N2 N -0.1133(10) 0.0958(10) 0.1183(2) 0.0256(18) Uani 1 1 d . . .
N1 N 0.2515(10) 0.2832(10) 0.0304(2) 0.0257(19) Uani 1 1 d . . .
C1 C 0.2301(14) 0.3437(14) -0.0144(3) 0.034(2) Uani 1 1 d . . .
H1 H 0.3324 0.4052 -0.0297 0.040 Uiso 1 1 calc R . .
C2 C 0.0486(14) 0.3161(14) -0.0408(3) 0.031(2) Uani 1 1 d . . .
C3 C 0.0378(14) 0.3799(13) -0.0900(3) 0.031(2) Uani 1 1 d . . .
H3 H 0.1449 0.4386 -0.1039 0.037 Uiso 1 1 calc R . .
C4 C -0.1306(14) 0.3559(14) -0.1177(3) 0.039(3) Uani 1 1 d . . .
H4 H -0.1379 0.3991 -0.1499 0.046 Uiso 1 1 calc R . .
C5 C -0.2902(14) 0.2650(14) -0.0963(3) 0.030(2) Uani 1 1 d . . .
C6 C -0.2807(14) 0.2058(14) -0.0491(3) 0.035(3) Uani 1 1 d . . .
H6 H -0.3884 0.1468 -0.0356 0.042 Uiso 1 1 calc R . .
C7 C -0.1140(15) 0.2307(12) -0.0200(3) 0.026(2) Uani 1 1 d . . .
C8 C -0.0972(13) 0.0667(14) 0.1647(3) 0.033(2) Uani 1 1 d . . .
H8 H -0.2029 0.0163 0.1812 0.040 Uiso 1 1 calc R . .
C9 C 0.0756(14) 0.1082(13) 0.1923(3) 0.027(2) Uani 1 1 d . . .
C10 C 0.0763(14) 0.0854(15) 0.2438(3) 0.041(3) Uani 1 1 d . . .
H10 H -0.0360 0.0442 0.2592 0.049 Uiso 1 1 calc R . .
C11 C 0.2377(15) 0.1226(15) 0.2712(3) 0.042(3) Uani 1 1 d . . .
H11 H 0.2348 0.1080 0.3051 0.051 Uiso 1 1 calc R . .
C12 C 0.4059(15) 0.1820(14) 0.2489(3) 0.036(3) Uani 1 1 d . . .
C13 C 0.4119(15) 0.2115(14) 0.1985(3) 0.037(3) Uani 1 1 d . . .
H13 H 0.5232 0.2591 0.1839 0.045 Uiso 1 1 calc R . .
C14 C 0.2461(15) 0.1678(13) 0.1700(3) 0.032(3) Uani 1 1 d . . .


_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
O5 N1 1.417(8) . ?
O5 H5 0.8200 . ?
Ni1 O2 1.829(5) . ?
Ni1 O1 1.832(5) . ?
Ni1 N2 1.865(7) . ?
Ni1 N1 1.865(7) . ?
O3 C5 1.364(9) . ?
O3 H3A 0.8200 . ?
O1 C7 1.343(9) . ?
O4 N2 1.419(8) . ?
O4 H4A 0.8201 . ?
O6 C12 1.359(10) . ?
O6 H5A 0.8201 . ?
O2 C14 1.343(10) . ?
N2 C8 1.284(9) . ?
N1 C1 1.301(10) . ?
C1 C2 1.447(11) . ?
C1 H1 0.9300 . ?
C2 C7 1.397(13) . ?
C2 C3 1.415(11) . ?
C3 C4 1.386(11) . ?
C3 H3 0.9300 . ?
C4 C5 1.405(13) . ?
C4 H4 0.9300 . ?
C5 C6 1.354(11) . ?
C6 C7 1.399(11) . ?
C6 H6 0.9300 . ?
C8 C9 1.430(11) . ?
C8 H8 0.9300 . ?
C9 C14 1.392(12) . ?
C9 C10 1.410(11) . ?
C10 C11 1.357(12) . ?
C10 H10 0.9300 . ?
C11 C12 1.378(13) . ?
C11 H11 0.9300 . ?
C12 C13 1.390(11) . ?
C13 C14 1.407(12) . ?
C13 H13 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
N1 O5 H5 109.5 . . ?
O2 Ni1 O1 179.1(3) . . ?
O2 Ni1 N2 92.6(3) . . ?
O1 Ni1 N2 87.2(3) . . ?
O2 Ni1 N1 87.3(3) . . ?
O1 Ni1 N1 93.0(3) . . ?
N2 Ni1 N1 178.0(3) . . ?
C5 O3 H3A 113.1 . . ?
C7 O1 Ni1 128.0(6) . . ?
N2 O4 H4A 108.6 . . ?
C12 O6 H5A 111.4 . . ?
C14 O2 Ni1 128.7(6) . . ?
C8 N2 O4 112.4(7) . . ?
C8 N2 Ni1 129.7(6) . . ?
O4 N2 Ni1 117.9(4) . . ?
C1 N1 O5 110.9(7) . . ?
C1 N1 Ni1 130.6(6) . . ?
O5 N1 Ni1 118.0(4) . . ?
N1 C1 C2 120.7(9) . . ?
N1 C1 H1 119.7 . . ?
C2 C1 H1 119.7 . . ?
C7 C2 C3 119.3(8) . . ?
C7 C2 C1 123.1(8) . . ?
C3 C2 C1 117.6(9) . . ?
C4 C3 C2 120.7(9) . . ?
C4 C3 H3 119.6 . . ?
C2 C3 H3 119.6 . . ?
C3 C4 C5 118.9(8) . . ?
C3 C4 H4 120.6 . . ?
C5 C4 H4 120.6 . . ?
C6 C5 O3 123.3(9) . . ?
C6 C5 C4 120.4(8) . . ?
O3 C5 C4 116.2(7) . . ?
C5 C6 C7 122.0(9) . . ?
C5 C6 H6 119.0 . . ?
C7 C6 H6 119.0 . . ?
O1 C7 C2 123.9(8) . . ?
O1 C7 C6 117.4(9) . . ?
C2 C7 C6 118.6(7) . . ?
N2 C8 C9 123.1(8) . . ?
N2 C8 H8 118.5 . . ?
C9 C8 H8 118.5 . . ?
C14 C9 C10 118.4(8) . . ?
C14 C9 C8 122.2(7) . . ?
C10 C9 C8 119.4(8) . . ?
C11 C10 C9 121.2(9) . . ?
C11 C10 H10 119.4 . . ?
C9 C10 H10 119.4 . . ?
C10 C11 C12 120.2(8) . . ?
C10 C11 H11 119.9 . . ?
C12 C11 H11 119.9 . . ?
O6 C12 C11 123.6(8) . . ?
O6 C12 C13 115.5(9) . . ?
C11 C12 C13 121.0(8) . . ?
C12 C13 C14 118.6(9) . . ?
C12 C13 H13 120.7 . . ?
C14 C13 H13 120.7 . . ?
O2 C14 C9 123.3(7) . . ?
O2 C14 C13 116.1(9) . . ?
C9 C14 C13 120.5(8) . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
O2 Ni1 O1 C7 -112(17) . . . . ?
N2 Ni1 O1 C7 171.7(7) . . . . ?
N1 Ni1 O1 C7 -6.2(7) . . . . ?
O1 Ni1 O2 C14 -82(17) . . . . ?
N2 Ni1 O2 C14 -5.5(8) . . . . ?
N1 Ni1 O2 C14 172.4(8) . . . . ?
O2 Ni1 N2 C8 2.3(9) . . . . ?
O1 Ni1 N2 C8 -178.5(9) . . . . ?
N1 Ni1 N2 C8 -85(8) . . . . ?
O2 Ni1 N2 O4 -176.6(6) . . . . ?
O1 Ni1 N2 O4 2.5(6) . . . . ?
N1 Ni1 N2 O4 96(7) . . . . ?
O2 Ni1 N1 C1 -170.9(9) . . . . ?
O1 Ni1 N1 C1 9.9(9) . . . . ?
N2 Ni1 N1 C1 -83(8) . . . . ?
O2 Ni1 N1 O5 0.8(6) . . . . ?
O1 Ni1 N1 O5 -178.4(6) . . . . ?
N2 Ni1 N1 O5 88(7) . . . . ?
O5 N1 C1 C2 178.7(7) . . . . ?
Ni1 N1 C1 C2 -9.2(14) . . . . ?
N1 C1 C2 C7 2.2(14) . . . . ?
N1 C1 C2 C3 -177.9(9) . . . . ?
C7 C2 C3 C4 -1.0(14) . . . . ?
C1 C2 C3 C4 179.1(8) . . . . ?
C2 C3 C4 C5 -0.7(13) . . . . ?
C3 C4 C5 C6 1.4(14) . . . . ?
C3 C4 C5 O3 178.9(8) . . . . ?
O3 C5 C6 C7 -177.7(8) . . . . ?
C4 C5 C6 C7 -0.4(15) . . . . ?
Ni1 O1 C7 C2 2.5(13) . . . . ?
Ni1 O1 C7 C6 -178.3(6) . . . . ?
C3 C2 C7 O1 -178.8(8) . . . . ?
C1 C2 C7 O1 1.0(14) . . . . ?
C3 C2 C7 C6 2.0(13) . . . . ?
C1 C2 C7 C6 -178.2(9) . . . . ?
C5 C6 C7 O1 179.5(9) . . . . ?
C5 C6 C7 C2 -1.3(14) . . . . ?
O4 N2 C8 C9 -178.4(8) . . . . ?
Ni1 N2 C8 C9 2.6(15) . . . . ?
N2 C8 C9 C14 -5.9(15) . . . . ?
N2 C8 C9 C10 175.2(9) . . . . ?
C14 C9 C10 C11 0.8(15) . . . . ?
C8 C9 C10 C11 179.7(9) . . . . ?
C9 C10 C11 C12 -0.7(16) . . . . ?
C10 C11 C12 O6 -177.5(9) . . . . ?
C10 C11 C12 C13 2.4(15) . . . . ?
O6 C12 C13 C14 175.8(8) . . . . ?
C11 C12 C13 C14 -4.1(15) . . . . ?
Ni1 O2 C14 C9 3.9(13) . . . . ?
Ni1 O2 C14 C13 -172.1(6) . . . . ?
C10 C9 C14 O2 -178.4(9) . . . . ?
C8 C9 C14 O2 2.7(14) . . . . ?
C10 C9 C14 C13 -2.6(14) . . . . ?
C8 C9 C14 C13 178.5(9) . . . . ?
C12 C13 C14 O2 -179.6(8) . . . . ?
C12 C13 C14 C9 4.2(14) . . . . ?

_diffrn_measured_fraction_theta_max 0.993
_diffrn_reflns_theta_full        25.24
_diffrn_measured_fraction_theta_full 0.993
_refine_diff_density_max         0.540
_refine_diff_density_min         -0.561
_refine_diff_density_rms         0.105
####################################################################### 
# 
# 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_Complex-5
_database_code_depnum_ccdc_archive 'CCDC 1402354'
_audit_update_record             
;
2015-06-22 deposited with the CCDC.
2015-09-21 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C14 H12 N2 Ni O6, 2(C3 H7 N O)'
_chemical_formula_sum            'C20 H26 N4 Ni O8'
_chemical_formula_weight         509.14

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'
Ni Ni 0.3393 1.1124 '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                   6.2331(6)
_cell_length_b                   7.2148(6)
_cell_length_c                   13.1150(12)
_cell_angle_alpha                90.288(5)
_cell_angle_beta                 101.143(5)
_cell_angle_gamma                100.988(5)
_cell_volume                     567.52(9)
_cell_formula_units_Z            1
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    ?
_cell_measurement_theta_min      ?
_cell_measurement_theta_max      ?

_exptl_crystal_description       Neddle
_exptl_crystal_colour            Blue
_exptl_crystal_size_max          0.32
_exptl_crystal_size_mid          0.24
_exptl_crystal_size_min          0.12
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.490
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             266
_exptl_absorpt_coefficient_mu    0.908
_exptl_absorpt_correction_type   multi-Scan
_exptl_absorpt_correction_T_min  0.770
_exptl_absorpt_correction_T_max  0.897
_exptl_absorpt_process_details   multi-Scan

_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            6679
_diffrn_reflns_av_R_equivalents  0.0299
_diffrn_reflns_av_sigmaI/netI    0.0233
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_theta_min         1.58
_diffrn_reflns_theta_max         25.25
_reflns_number_total             2044
_reflns_number_gt                1883
_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 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)+(0.0000P)²+7.0000P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         2044
_refine_ls_number_parameters     141
_refine_ls_number_restraints     3
_refine_ls_R_factor_all          0.0754
_refine_ls_R_factor_gt           0.0738
_refine_ls_wR_factor_ref         0.1888
_refine_ls_wR_factor_gt          0.1880
_refine_ls_goodness_of_fit_ref   1.015
_refine_ls_restrained_S_all      1.600
_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
C3 C 0.2803(9) -0.1238(8) 0.3739(5) 0.033(2) Uani 1 1 d G . .
C2 C 0.4044(11) 0.0570(7) 0.3703(5) 0.032(2) Uani 1 1 d G . .
C7 C 0.5824(11) 0.0852(7) 0.3188(6) 0.041(3) Uani 1 1 d G . .
H7 H 0.6655 0.2061 0.3164 0.050 Uiso 1 1 calc R . .
C6 C 0.6362(10) -0.0673(9) 0.2710(6) 0.043(3) Uani 1 1 d G . .
H6 H 0.7553 -0.0485 0.2366 0.052 Uiso 1 1 calc R . .
C5 C 0.5121(12) -0.2481(8) 0.2747(5) 0.039(2) Uani 1 1 d GD . .
C4 C 0.3341(11) -0.2763(7) 0.3261(5) 0.038(2) Uani 1 1 d G . .
H4 H 0.2510 -0.3973 0.3286 0.045 Uiso 1 1 calc R . .
Ni1 Ni 0.0000 0.0000 0.5000 0.0290(5) Uani 1 2 d S . .
O2 O 0.1816(14) 0.3906(10) 0.5060(7) 0.048(2) Uani 1 1 d . . .
H2 H 0.0779 0.3812 0.5370 0.072 Uiso 1 1 calc R . .
O3 O 0.5592(16) -0.4052(12) 0.2290(7) 0.059(2) Uani 1 1 d D . .
H3 H 0.6666 -0.3727 0.2011 0.089 Uiso 1 1 calc R . .
O1 O 0.1124(12) -0.1564(9) 0.4255(6) 0.0390(18) Uani 1 1 d D . .
N1 N 0.1933(14) 0.2052(11) 0.4668(7) 0.0333(19) Uani 1 1 d D . .
C1 C 0.3565(18) 0.2213(14) 0.4187(8) 0.036(2) Uani 1 1 d . . .
H1A H 0.4447 0.3396 0.4149 0.043 Uiso 1 1 calc R . .
O4 O 1.209(3) 0.306(2) -0.0795(11) 0.108(5) Uani 1 1 d . . .
N2 N 0.9750(19) 0.2492(15) 0.0301(9) 0.054(3) Uani 1 1 d . . .
C9 C 1.113(3) 0.253(3) 0.1287(15) 0.107(7) Uani 1 1 d . . .
H9A H 1.1096 0.1267 0.1514 0.161 Uiso 1 1 calc R . .
H9B H 1.0615 0.3254 0.1773 0.161 Uiso 1 1 calc R . .
H9C H 1.2635 0.3109 0.1247 0.161 Uiso 1 1 calc R . .
C8 C 0.736(3) 0.203(3) 0.0233(19) 0.115(8) Uani 1 1 d . . .
H8A H 0.6615 0.2344 -0.0435 0.172 Uiso 1 1 calc R . .
H8B H 0.6961 0.2729 0.0768 0.172 Uiso 1 1 calc R . .
H8C H 0.6912 0.0698 0.0323 0.172 Uiso 1 1 calc R . .
C10 C 1.052(5) 0.280(3) -0.057(2) 0.133(11) Uani 1 1 d . . .
H10 H 0.9367 0.2774 -0.1139 0.160 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
C3 O1 1.337(8) . ?
C3 C2 1.3900 . ?
C3 C4 1.3900 . ?
C2 C7 1.3900 . ?
C2 C1 1.448(11) . ?
C7 C6 1.3900 . ?
C7 H7 0.9300 . ?
C6 C5 1.3900 . ?
C6 H6 0.9300 . ?
C5 O3 1.385(8) . ?
C5 C4 1.3900 . ?
C4 H4 0.9300 . ?
Ni1 O1 1.809(7) 2_556 ?
Ni1 O1 1.809(7) . ?
Ni1 N1 1.834(8) 2_556 ?
Ni1 N1 1.834(8) . ?
O2 N1 1.451(10) . ?
O2 H2 0.8200 . ?
O3 H3 0.8200 . ?
N1 C1 1.285(13) . ?
C1 H1A 0.9300 . ?
O4 C10 1.06(3) . ?
N2 C10 1.32(2) . ?
N2 C9 1.406(19) . ?
N2 C8 1.45(2) . ?
C9 H9A 0.9600 . ?
C9 H9B 0.9600 . ?
C9 H9C 0.9600 . ?
C8 H8A 0.9600 . ?
C8 H8B 0.9600 . ?
C8 H8C 0.9600 . ?
C10 H10 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 C3 C2 121.4(5) . . ?
O1 C3 C4 118.6(5) . . ?
C2 C3 C4 120.0 . . ?
C3 C2 C7 120.0 . . ?
C3 C2 C1 122.5(6) . . ?
C7 C2 C1 117.5(6) . . ?
C2 C7 C6 120.0 . . ?
C2 C7 H7 120.0 . . ?
C6 C7 H7 120.0 . . ?
C5 C6 C7 120.0 . . ?
C5 C6 H6 120.0 . . ?
C7 C6 H6 120.0 . . ?
O3 C5 C6 122.4(6) . . ?
O3 C5 C4 117.6(6) . . ?
C6 C5 C4 120.0 . . ?
C5 C4 C3 120.0 . . ?
C5 C4 H4 120.0 . . ?
C3 C4 H4 120.0 . . ?
O1 Ni1 O1 179.999(2) 2_556 . ?
O1 Ni1 N1 90.8(3) 2_556 2_556 ?
O1 Ni1 N1 89.2(3) . 2_556 ?
O1 Ni1 N1 89.2(3) 2_556 . ?
O1 Ni1 N1 90.8(3) . . ?
N1 Ni1 N1 179.999(1) 2_556 . ?
N1 O2 H2 109.5 . . ?
C5 O3 H3 109.5 . . ?
C3 O1 Ni1 131.7(5) . . ?
C1 N1 O2 109.0(8) . . ?
C1 N1 Ni1 132.6(7) . . ?
O2 N1 Ni1 118.2(6) . . ?
N1 C1 C2 120.6(9) . . ?
N1 C1 H1A 119.7 . . ?
C2 C1 H1A 119.7 . . ?
C10 N2 C9 123.4(19) . . ?
C10 N2 C8 119(2) . . ?
C9 N2 C8 118.0(15) . . ?
N2 C9 H9A 109.5 . . ?
N2 C9 H9B 109.5 . . ?
H9A C9 H9B 109.5 . . ?
N2 C9 H9C 109.5 . . ?
H9A C9 H9C 109.5 . . ?
H9B C9 H9C 109.5 . . ?
N2 C8 H8A 109.5 . . ?
N2 C8 H8B 109.5 . . ?
H8A C8 H8B 109.5 . . ?
N2 C8 H8C 109.5 . . ?
H8A C8 H8C 109.5 . . ?
H8B C8 H8C 109.5 . . ?
O4 C10 N2 138(3) . . ?
O4 C10 H10 111.2 . . ?
N2 C10 H10 111.2 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
O1 C3 C2 C7 178.0(7) . . . . ?
C4 C3 C2 C7 0.0 . . . . ?
O1 C3 C2 C1 -2.0(9) . . . . ?
C4 C3 C2 C1 -179.9(8) . . . . ?
C3 C2 C7 C6 0.0 . . . . ?
C1 C2 C7 C6 179.9(7) . . . . ?
C2 C7 C6 C5 0.0 . . . . ?
C7 C6 C5 O3 -179.6(8) . . . . ?
C7 C6 C5 C4 0.0 . . . . ?
O3 C5 C4 C3 179.6(8) . . . . ?
C6 C5 C4 C3 0.0 . . . . ?
O1 C3 C4 C5 -178.0(7) . . . . ?
C2 C3 C4 C5 0.0 . . . . ?
C2 C3 O1 Ni1 -0.3(11) . . . . ?
C4 C3 O1 Ni1 177.6(5) . . . . ?
O1 Ni1 O1 C3 78(6) 2_556 . . . ?
N1 Ni1 O1 C3 -176.6(8) 2_556 . . . ?
N1 Ni1 O1 C3 3.4(8) . . . . ?
O1 Ni1 N1 C1 173.7(11) 2_556 . . . ?
O1 Ni1 N1 C1 -6.3(11) . . . . ?
N1 Ni1 N1 C1 -158(20) 2_556 . . . ?
O1 Ni1 N1 O2 -1.0(7) 2_556 . . . ?
O1 Ni1 N1 O2 179.0(7) . . . . ?
N1 Ni1 N1 O2 28(20) 2_556 . . . ?
O2 N1 C1 C2 -179.2(8) . . . . ?
Ni1 N1 C1 C2 5.8(16) . . . . ?
C3 C2 C1 N1 -0.6(13) . . . . ?
C7 C2 C1 N1 179.5(8) . . . . ?
C9 N2 C10 O4 3(4) . . . . ?
C8 N2 C10 O4 -175(3) . . . . ?

_diffrn_measured_fraction_theta_max 0.990
_diffrn_reflns_theta_full        25.25
_diffrn_measured_fraction_theta_full 0.990
_refine_diff_density_max         1.084
_refine_diff_density_min         -1.225
_refine_diff_density_rms         0.158
####################################################################### 
# 
# 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_Complex-7
_database_code_depnum_ccdc_archive 'CCDC 1402355'
_audit_update_record             
;
2015-06-22 deposited with the CCDC.
2015-09-21 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C40 H40 N6 O6 Zn'
_chemical_formula_sum            'C40 H40 N6 O6 Zn'
_chemical_formula_weight         766.17

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'

_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                   7.7539(6)
_cell_length_b                   9.7058(8)
_cell_length_c                   13.6203(10)
_cell_angle_alpha                75.256(5)
_cell_angle_beta                 79.970(5)
_cell_angle_gamma                72.318(5)
_cell_volume                     939.22(13)
_cell_formula_units_Z            1
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    ?
_cell_measurement_theta_min      ?
_cell_measurement_theta_max      ?

_exptl_crystal_description       Block
_exptl_crystal_colour            Colourless
_exptl_crystal_size_max          0.32
_exptl_crystal_size_mid          0.24
_exptl_crystal_size_min          0.12
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.355
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             400
_exptl_absorpt_coefficient_mu    0.709
_exptl_absorpt_correction_type   multi-Scan
_exptl_absorpt_correction_T_min  0.815
_exptl_absorpt_correction_T_max  0.918
_exptl_absorpt_process_details   multi-Scan

_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            13308
_diffrn_reflns_av_R_equivalents  0.0288
_diffrn_reflns_av_sigmaI/netI    0.0309
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_theta_min         1.55
_diffrn_reflns_theta_max         25.25
_reflns_number_total             3398
_reflns_number_gt                2704
_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 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)+(0.0400P)²+0.3000P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         3398
_refine_ls_number_parameters     241
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0491
_refine_ls_R_factor_gt           0.0358
_refine_ls_wR_factor_ref         0.0882
_refine_ls_wR_factor_gt          0.0818
_refine_ls_goodness_of_fit_ref   1.008
_refine_ls_restrained_S_all      1.008
_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
Zn1 Zn 0.5000 0.0000 0.0000 0.05064(15) Uani 1 2 d S . .
O1 O 0.85914(19) -0.14910(17) 0.07574(11) 0.0520(4) Uani 1 1 d . . .
H1A H 0.7814 -0.1507 0.1250 0.078 Uiso 1 1 d R . .
O2 O 0.50757(18) 0.09698(16) -0.14925(10) 0.0438(4) Uani 1 1 d . . .
O3 O 0.7328(2) 0.18900(19) -0.50051(11) 0.0621(5) Uani 1 1 d . . .
H3A H 0.6239 0.2265 -0.5061 0.093 Uiso 1 1 d R . .
N1 N 0.7762(2) -0.07772(18) -0.01461(12) 0.0374(4) Uani 1 1 d . . .
N2 N 0.5462(2) 0.2089(2) 0.04213(14) 0.0461(5) Uani 1 1 d . . .
N3 N 1.3828(3) 0.3280(3) 0.45461(15) 0.0617(6) Uani 1 1 d . . .
C1 C 0.8869(3) -0.0584(2) -0.09469(16) 0.0389(5) Uani 1 1 d . . .
H1 H 1.0108 -0.0925 -0.0875 0.047 Uiso 1 1 calc R . .
C2 C 0.8327(3) 0.0133(2) -0.19636(15) 0.0359(5) Uani 1 1 d . . .
C3 C 0.9717(3) 0.0091(2) -0.27767(16) 0.0430(5) Uani 1 1 d . . .
H3 H 1.0913 -0.0352 -0.2628 0.052 Uiso 1 1 calc R . .
C4 C 0.9403(3) 0.0667(3) -0.37778(17) 0.0478(5) Uani 1 1 d . . .
H4 H 1.0362 0.0617 -0.4295 0.057 Uiso 1 1 calc R . .
C5 C 0.7606(3) 0.1333(2) -0.40028(16) 0.0431(5) Uani 1 1 d . . .
C6 C 0.6192(3) 0.1415(2) -0.32250(15) 0.0390(5) Uani 1 1 d . . .
H6 H 0.5007 0.1868 -0.3392 0.047 Uiso 1 1 calc R . .
C7 C 0.6481(3) 0.0841(2) -0.21931(15) 0.0353(5) Uani 1 1 d . . .
C12 C 0.4851(4) 0.2384(3) 0.13439(19) 0.0609(7) Uani 1 1 d . . .
H12 H 0.4016 0.1911 0.1752 0.073 Uiso 1 1 calc R . .
C11 C 0.5396(4) 0.3353(3) 0.17207(19) 0.0644(7) Uani 1 1 d . . .
H11 H 0.4933 0.3513 0.2372 0.077 Uiso 1 1 calc R . .
C10 C 0.6620(3) 0.4090(2) 0.11434(19) 0.0502(6) Uani 1 1 d . . .
C9 C 0.7239(3) 0.3800(3) 0.01835(18) 0.0506(6) Uani 1 1 d . . .
H9 H 0.8064 0.4269 -0.0242 0.061 Uiso 1 1 calc R . .
C8 C 0.6628(3) 0.2810(2) -0.01428(17) 0.0455(5) Uani 1 1 d . . .
H8 H 0.7058 0.2639 -0.0795 0.055 Uiso 1 1 calc R . .
C13 C 0.7261(4) 0.5131(3) 0.1557(2) 0.0665(7) Uani 1 1 d . . .
H13B H 0.6232 0.5734 0.1914 0.080 Uiso 1 1 calc R . .
H13A H 0.7760 0.5787 0.0994 0.080 Uiso 1 1 calc R . .
C14 C 0.8714(4) 0.4281(3) 0.2289(2) 0.0669(8) Uani 1 1 d . . .
H14A H 0.8269 0.3530 0.2797 0.080 Uiso 1 1 calc R . .
H14B H 0.9799 0.3781 0.1909 0.080 Uiso 1 1 calc R . .
C15 C 0.9205(4) 0.5258(3) 0.2820(2) 0.0740(8) Uani 1 1 d . . .
H15B H 0.8149 0.5655 0.3265 0.089 Uiso 1 1 calc R . .
H15A H 0.9475 0.6087 0.2309 0.089 Uiso 1 1 calc R . .
C16 C 1.0795(3) 0.4541(3) 0.34456(18) 0.0566(6) Uani 1 1 d . . .
C19 C 1.1787(4) 0.5381(3) 0.3630(2) 0.0743(8) Uani 1 1 d . . .
H19 H 1.1459 0.6401 0.3384 0.089 Uiso 1 1 calc R . .
C20 C 1.3261(4) 0.4727(3) 0.4174(2) 0.0761(9) Uani 1 1 d . . .
H20 H 1.3901 0.5330 0.4290 0.091 Uiso 1 1 calc R . .
C18 C 1.2889(4) 0.2454(3) 0.4365(2) 0.0743(8) Uani 1 1 d . . .
H18 H 1.3262 0.1436 0.4614 0.089 Uiso 1 1 calc R . .
C17 C 1.1378(4) 0.3026(3) 0.3823(2) 0.0736(8) Uani 1 1 d . . .
H17 H 1.0763 0.2401 0.3714 0.088 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
Zn1 O2 2.0100(13) . ?
Zn1 O2 2.0100(13) 2_655 ?
Zn1 N1 2.0348(16) 2_655 ?
Zn1 N1 2.0348(16) . ?
Zn1 N2 2.3817(18) 2_655 ?
Zn1 N2 2.3817(18) . ?
O1 N1 1.4069(19) . ?
O1 H1A 0.8200 . ?
O2 C7 1.315(2) . ?
O3 C5 1.363(2) . ?
O3 H3A 0.8200 . ?
N1 C1 1.277(3) . ?
N2 C8 1.329(3) . ?
N2 C12 1.334(3) . ?
N3 C18 1.324(3) . ?
N3 C20 1.327(3) . ?
C1 C2 1.454(3) . ?
C1 H1 0.9300 . ?
C2 C3 1.403(3) . ?
C2 C7 1.438(3) . ?
C3 C4 1.370(3) . ?
C3 H3 0.9300 . ?
C4 C5 1.398(3) . ?
C4 H4 0.9300 . ?
C5 C6 1.384(3) . ?
C6 C7 1.404(3) . ?
C6 H6 0.9300 . ?
C12 C11 1.375(3) . ?
C12 H12 0.9300 . ?
C11 C10 1.377(3) . ?
C11 H11 0.9300 . ?
C10 C9 1.380(3) . ?
C10 C13 1.509(3) . ?
C9 C8 1.383(3) . ?
C9 H9 0.9300 . ?
C8 H8 0.9300 . ?
C13 C14 1.534(3) . ?
C13 H13B 0.9700 . ?
C13 H13A 0.9700 . ?
C14 C15 1.494(3) . ?
C14 H14A 0.9700 . ?
C14 H14B 0.9700 . ?
C15 C16 1.508(3) . ?
C15 H15B 0.9700 . ?
C15 H15A 0.9700 . ?
C16 C19 1.368(4) . ?
C16 C17 1.387(4) . ?
C19 C20 1.369(4) . ?
C19 H19 0.9300 . ?
C20 H20 0.9300 . ?
C18 C17 1.387(4) . ?
C18 H18 0.9300 . ?
C17 H17 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
O2 Zn1 O2 180.0 . 2_655 ?
O2 Zn1 N1 90.02(6) . 2_655 ?
O2 Zn1 N1 89.98(6) 2_655 2_655 ?
O2 Zn1 N1 89.98(6) . . ?
O2 Zn1 N1 90.02(6) 2_655 . ?
N1 Zn1 N1 180.0 2_655 . ?
O2 Zn1 N2 88.43(6) . 2_655 ?
O2 Zn1 N2 91.57(6) 2_655 2_655 ?
N1 Zn1 N2 85.87(6) 2_655 2_655 ?
N1 Zn1 N2 94.13(6) . 2_655 ?
O2 Zn1 N2 91.57(6) . . ?
O2 Zn1 N2 88.43(6) 2_655 . ?
N1 Zn1 N2 94.13(6) 2_655 . ?
N1 Zn1 N2 85.87(6) . . ?
N2 Zn1 N2 180.00(8) 2_655 . ?
N1 O1 H1A 110.0 . . ?
C7 O2 Zn1 128.24(12) . . ?
C5 O3 H3A 110.3 . . ?
C1 N1 O1 114.70(15) . . ?
C1 N1 Zn1 128.10(13) . . ?
O1 N1 Zn1 116.85(12) . . ?
C8 N2 C12 116.3(2) . . ?
C8 N2 Zn1 122.13(14) . . ?
C12 N2 Zn1 120.09(16) . . ?
C18 N3 C20 116.6(2) . . ?
N1 C1 C2 124.49(17) . . ?
N1 C1 H1 117.8 . . ?
C2 C1 H1 117.8 . . ?
C3 C2 C7 118.22(18) . . ?
C3 C2 C1 116.95(17) . . ?
C7 C2 C1 124.80(18) . . ?
C4 C3 C2 123.42(19) . . ?
C4 C3 H3 118.3 . . ?
C2 C3 H3 118.3 . . ?
C3 C4 C5 118.4(2) . . ?
C3 C4 H4 120.8 . . ?
C5 C4 H4 120.8 . . ?
O3 C5 C6 122.48(19) . . ?
O3 C5 C4 117.26(19) . . ?
C6 C5 C4 120.26(19) . . ?
C5 C6 C7 122.38(18) . . ?
C5 C6 H6 118.8 . . ?
C7 C6 H6 118.8 . . ?
O2 C7 C6 119.17(17) . . ?
O2 C7 C2 123.51(18) . . ?
C6 C7 C2 117.32(18) . . ?
N2 C12 C11 123.2(2) . . ?
N2 C12 H12 118.4 . . ?
C11 C12 H12 118.4 . . ?
C12 C11 C10 120.6(2) . . ?
C12 C11 H11 119.7 . . ?
C10 C11 H11 119.7 . . ?
C11 C10 C9 116.3(2) . . ?
C11 C10 C13 121.2(2) . . ?
C9 C10 C13 122.5(2) . . ?
C10 C9 C8 119.7(2) . . ?
C10 C9 H9 120.1 . . ?
C8 C9 H9 120.1 . . ?
N2 C8 C9 123.8(2) . . ?
N2 C8 H8 118.1 . . ?
C9 C8 H8 118.1 . . ?
C10 C13 C14 111.4(2) . . ?
C10 C13 H13B 109.4 . . ?
C14 C13 H13B 109.4 . . ?
C10 C13 H13A 109.4 . . ?
C14 C13 H13A 109.4 . . ?
H13B C13 H13A 108.0 . . ?
C15 C14 C13 112.9(2) . . ?
C15 C14 H14A 109.0 . . ?
C13 C14 H14A 109.0 . . ?
C15 C14 H14B 109.0 . . ?
C13 C14 H14B 109.0 . . ?
H14A C14 H14B 107.8 . . ?
C14 C15 C16 116.1(2) . . ?
C14 C15 H15B 108.3 . . ?
C16 C15 H15B 108.3 . . ?
C14 C15 H15A 108.3 . . ?
C16 C15 H15A 108.3 . . ?
H15B C15 H15A 107.4 . . ?
C19 C16 C17 116.7(2) . . ?
C19 C16 C15 120.2(2) . . ?
C17 C16 C15 123.1(2) . . ?
C16 C19 C20 120.3(3) . . ?
C16 C19 H19 119.8 . . ?
C20 C19 H19 119.8 . . ?
N3 C20 C19 123.7(3) . . ?
N3 C20 H20 118.1 . . ?
C19 C20 H20 118.1 . . ?
N3 C18 C17 123.5(3) . . ?
N3 C18 H18 118.3 . . ?
C17 C18 H18 118.3 . . ?
C16 C17 C18 119.3(3) . . ?
C16 C17 H17 120.4 . . ?
C18 C17 H17 120.4 . . ?

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 Zn1 O2 C7 126(9) 2_655 . . . ?
N1 Zn1 O2 C7 -172.11(17) 2_655 . . . ?
N1 Zn1 O2 C7 7.89(17) . . . . ?
N2 Zn1 O2 C7 -86.25(17) 2_655 . . . ?
N2 Zn1 O2 C7 93.75(17) . . . . ?
O2 Zn1 N1 C1 0.60(18) . . . . ?
O2 Zn1 N1 C1 -179.40(18) 2_655 . . . ?
N1 Zn1 N1 C1 -72.2(14) 2_655 . . . ?
N2 Zn1 N1 C1 89.02(18) 2_655 . . . ?
N2 Zn1 N1 C1 -90.98(18) . . . . ?
O2 Zn1 N1 O1 173.50(13) . . . . ?
O2 Zn1 N1 O1 -6.50(13) 2_655 . . . ?
N1 Zn1 N1 O1 100.7(14) 2_655 . . . ?
N2 Zn1 N1 O1 -98.08(13) 2_655 . . . ?
N2 Zn1 N1 O1 81.92(13) . . . . ?
O2 Zn1 N2 C8 -40.89(16) . . . . ?
O2 Zn1 N2 C8 139.11(16) 2_655 . . . ?
N1 Zn1 N2 C8 -131.02(16) 2_655 . . . ?
N1 Zn1 N2 C8 48.98(16) . . . . ?
N2 Zn1 N2 C8 -125(6) 2_655 . . . ?
O2 Zn1 N2 C12 153.37(18) . . . . ?
O2 Zn1 N2 C12 -26.63(18) 2_655 . . . ?
N1 Zn1 N2 C12 63.24(18) 2_655 . . . ?
N1 Zn1 N2 C12 -116.76(18) . . . . ?
N2 Zn1 N2 C12 69(6) 2_655 . . . ?
O1 N1 C1 C2 -179.67(17) . . . . ?
Zn1 N1 C1 C2 -6.6(3) . . . . ?
N1 C1 C2 C3 -172.3(2) . . . . ?
N1 C1 C2 C7 6.0(3) . . . . ?
C7 C2 C3 C4 -1.1(3) . . . . ?
C1 C2 C3 C4 177.3(2) . . . . ?
C2 C3 C4 C5 0.0(3) . . . . ?
C3 C4 C5 O3 -179.6(2) . . . . ?
C3 C4 C5 C6 0.7(3) . . . . ?
O3 C5 C6 C7 -179.98(19) . . . . ?
C4 C5 C6 C7 -0.3(3) . . . . ?
Zn1 O2 C7 C6 169.48(14) . . . . ?
Zn1 O2 C7 C2 -10.4(3) . . . . ?
C5 C6 C7 O2 179.39(19) . . . . ?
C5 C6 C7 C2 -0.7(3) . . . . ?
C3 C2 C7 O2 -178.74(19) . . . . ?
C1 C2 C7 O2 3.0(3) . . . . ?
C3 C2 C7 C6 1.4(3) . . . . ?
C1 C2 C7 C6 -176.88(18) . . . . ?
C8 N2 C12 C11 -1.2(4) . . . . ?
Zn1 N2 C12 C11 165.3(2) . . . . ?
N2 C12 C11 C10 0.5(4) . . . . ?
C12 C11 C10 C9 0.3(4) . . . . ?
C12 C11 C10 C13 -178.6(2) . . . . ?
C11 C10 C9 C8 -0.3(3) . . . . ?
C13 C10 C9 C8 178.61(19) . . . . ?
C12 N2 C8 C9 1.2(3) . . . . ?
Zn1 N2 C8 C9 -165.05(16) . . . . ?
C10 C9 C8 N2 -0.5(3) . . . . ?
C11 C10 C13 C14 78.3(3) . . . . ?
C9 C10 C13 C14 -100.5(3) . . . . ?
C10 C13 C14 C15 -172.4(2) . . . . ?
C13 C14 C15 C16 -172.3(3) . . . . ?
C14 C15 C16 C19 154.8(3) . . . . ?
C14 C15 C16 C17 -22.3(4) . . . . ?
C17 C16 C19 C20 -0.9(4) . . . . ?
C15 C16 C19 C20 -178.2(3) . . . . ?
C18 N3 C20 C19 0.2(4) . . . . ?
C16 C19 C20 N3 0.5(5) . . . . ?
C20 N3 C18 C17 -0.3(4) . . . . ?
C19 C16 C17 C18 0.7(4) . . . . ?
C15 C16 C17 C18 178.0(3) . . . . ?
N3 C18 C17 C16 -0.1(5) . . . . ?

_diffrn_measured_fraction_theta_max 0.994
_diffrn_reflns_theta_full        25.25
_diffrn_measured_fraction_theta_full 0.994
_refine_diff_density_max         0.278
_refine_diff_density_min         -0.217
_refine_diff_density_rms         0.042
####################################################################### 
# 
# 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_Complex-2
_database_code_depnum_ccdc_archive 'CCDC 1402356'
_audit_update_record             
;
2015-06-22 deposited with the CCDC.
2015-09-21 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C14 H12 Cu N2 O6, 2(C4 H9 N O)'
_chemical_formula_sum            'C22 H30 Cu N4 O8'
_chemical_formula_weight         542.05

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           Monoclinic
_symmetry_space_group_name_H-M   'P 21/n'
_space_group_name_Hall           '-P 2yn'
loop_
_symmetry_equiv_pos_as_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                   9.3108(3)
_cell_length_b                   7.1558(2)
_cell_length_c                   19.0122(6)
_cell_angle_alpha                90.00
_cell_angle_beta                 94.749(2)
_cell_angle_gamma                90.00
_cell_volume                     1262.36(7)
_cell_formula_units_Z            2
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    ?
_cell_measurement_theta_min      ?
_cell_measurement_theta_max      ?

_exptl_crystal_description       Block
_exptl_crystal_colour            Black
_exptl_crystal_size_max          0.32
_exptl_crystal_size_mid          0.24
_exptl_crystal_size_min          0.12
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.426
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             566
_exptl_absorpt_coefficient_mu    0.917
_exptl_absorpt_correction_type   multi-Scan
_exptl_absorpt_correction_T_min  0.768
_exptl_absorpt_correction_T_max  0.768
_exptl_absorpt_process_details   multi-Scan

_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            16162
_diffrn_reflns_av_R_equivalents  0.0272
_diffrn_reflns_av_sigmaI/netI    0.0150
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_theta_min         2.15
_diffrn_reflns_theta_max         25.24
_reflns_number_total             2261
_reflns_number_gt                1830
_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 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)+(0.0900P)²+1.0000P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         2261
_refine_ls_number_parameters     165
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0602
_refine_ls_R_factor_gt           0.0526
_refine_ls_wR_factor_ref         0.1537
_refine_ls_wR_factor_gt          0.1438
_refine_ls_goodness_of_fit_ref   1.086
_refine_ls_restrained_S_all      1.086
_refine_ls_shift/su_max          0.002
_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 0.5000 0.5000 0.0000 0.0474(3) Uani 1 2 d S . .
C7 C 0.7185(4) 0.6786(5) 0.09639(16) 0.0494(8) Uani 1 1 d . . .
C6 C 0.7992(4) 0.8377(5) 0.11581(19) 0.0589(9) Uani 1 1 d . . .
H6 H 0.7849 0.9465 0.0894 0.071 Uiso 1 1 calc R . .
C1 C 0.6680(4) 0.3407(5) 0.12137(17) 0.0536(8) Uani 1 1 d . . .
H1 H 0.6908 0.2393 0.1508 0.064 Uiso 1 1 calc R . .
C2 C 0.7415(4) 0.5135(4) 0.13700(19) 0.0490(8) Uani 1 1 d . . .
C4 C 0.9243(4) 0.6762(6) 0.21377(19) 0.0626(9) Uani 1 1 d . . .
H4 H 0.9921 0.6760 0.2526 0.075 Uiso 1 1 calc R . .
C5 C 0.9001(4) 0.8370(5) 0.17363(19) 0.0597(9) Uani 1 1 d . . .
C3 C 0.8472(5) 0.5172(5) 0.1956(2) 0.0590(10) Uani 1 1 d . . .
H3 H 0.8644 0.4093 0.2223 0.071 Uiso 1 1 calc R . .
O1 O 0.6234(3) 0.6883(3) 0.04038(13) 0.0588(6) Uani 1 1 d . . .
O2 O 0.5172(3) 0.1349(3) 0.06319(15) 0.0727(8) Uani 1 1 d . . .
H2 H 0.4468 0.1334 0.0343 0.109 Uiso 1 1 calc R . .
O3 O 0.9726(4) 0.9985(3) 0.1888(2) 0.0812(10) Uani 1 1 d . . .
H3A H 1.0373 0.9793 0.2199 0.122 Uiso 1 1 calc R . .
N1 N 0.5724(3) 0.3168(4) 0.06912(15) 0.0537(7) Uani 1 1 d . . .
O4 O 0.1575(4) -0.0415(5) 0.30035(19) 0.0950(11) Uani 1 1 d . . .
C8 C 0.1994(7) 0.0728(15) 0.3448(3) 0.146(3) Uani 1 1 d . . .
C9 C 0.1306(6) 0.2923(7) 0.3312(3) 0.0929(15) Uani 1 1 d . . .
H9A H 0.0767 0.3267 0.3701 0.139 Uiso 1 1 calc R . .
H9B H 0.0684 0.2941 0.2883 0.139 Uiso 1 1 calc R . .
H9C H 0.2080 0.3794 0.3275 0.139 Uiso 1 1 calc R . .
C11 C 0.3422(7) -0.1372(10) 0.4019(3) 0.117(2) Uani 1 1 d . . .
H11A H 0.2946 -0.2185 0.3672 0.175 Uiso 1 1 calc R . .
H11B H 0.3301 -0.1848 0.4482 0.175 Uiso 1 1 calc R . .
H11C H 0.4430 -0.1312 0.3949 0.175 Uiso 1 1 calc R . .
C10 C 0.3323(7) 0.2130(12) 0.4440(3) 0.145(3) Uani 1 1 d . . .
H10A H 0.4253 0.2497 0.4305 0.218 Uiso 1 1 calc R . .
H10B H 0.3427 0.1554 0.4897 0.218 Uiso 1 1 calc R . .
H10C H 0.2717 0.3212 0.4456 0.218 Uiso 1 1 calc R . .
N2 N 0.2685(7) 0.0830(14) 0.3935(3) 0.169(4) Uani 1 1 d . . .


_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 1.892(2) 3_665 ?
Cu1 O1 1.892(2) . ?
Cu1 N1 1.937(3) . ?
Cu1 N1 1.937(3) 3_665 ?
C7 O1 1.329(4) . ?
C7 C6 1.397(5) . ?
C7 C2 1.418(5) . ?
C6 C5 1.386(5) . ?
C1 N1 1.290(4) . ?
C1 C2 1.432(5) . ?
C2 C3 1.425(5) . ?
C4 C3 1.374(5) . ?
C4 C5 1.389(5) . ?
C5 O3 1.357(4) . ?
O2 N1 1.401(3) . ?
O4 C8 1.216(8) . ?
C8 N2 1.086(8) . ?
C8 C9 1.708(11) . ?
C11 N2 1.721(11) . ?
C10 N2 1.430(8) . ?

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 O1 179.999(1) 3_665 . ?
O1 Cu1 N1 87.64(11) 3_665 . ?
O1 Cu1 N1 92.36(11) . . ?
O1 Cu1 N1 92.36(11) 3_665 3_665 ?
O1 Cu1 N1 87.64(11) . 3_665 ?
N1 Cu1 N1 180.0 . 3_665 ?
O1 C7 C6 118.5(3) . . ?
O1 C7 C2 122.7(3) . . ?
C6 C7 C2 118.8(3) . . ?
C5 C6 C7 121.4(3) . . ?
N1 C1 C2 124.2(3) . . ?
C7 C2 C3 118.3(3) . . ?
C7 C2 C1 123.9(3) . . ?
C3 C2 C1 117.7(3) . . ?
C3 C4 C5 119.4(3) . . ?
O3 C5 C6 117.3(3) . . ?
O3 C5 C4 122.3(3) . . ?
C6 C5 C4 120.5(3) . . ?
C4 C3 C2 121.6(3) . . ?
C7 O1 Cu1 129.0(2) . . ?
C1 N1 O2 114.2(3) . . ?
C1 N1 Cu1 127.7(2) . . ?
O2 N1 Cu1 118.0(2) . . ?
N2 C8 O4 140.5(13) . . ?
N2 C8 C9 104.8(9) . . ?
O4 C8 C9 114.7(7) . . ?
C8 N2 C10 143.2(12) . . ?
C8 N2 C11 102.7(9) . . ?
C10 N2 C11 113.2(7) . . ?

_diffrn_measured_fraction_theta_max 0.989
_diffrn_reflns_theta_full        25.24
_diffrn_measured_fraction_theta_full 0.989
_refine_diff_density_max         0.676
_refine_diff_density_min         -0.744
_refine_diff_density_rms         0.127
