# 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_3
_database_code_depnum_ccdc_archive 'CCDC 1053478'
_audit_update_record             
;
2015-03-12 deposited with the CCDC.
2015-05-13 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C20 H16 Cd O8'
_chemical_formula_weight         496.74

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'
Cd Cd -0.8075 1.2024 '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           orthorhombic
_symmetry_space_group_name_H-M   Pnma

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

_cell_length_a                   5.7913(3)
_cell_length_b                   40.564(2)
_cell_length_c                   7.9028(4)
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_volume                     1856.51(16)
_cell_formula_units_Z            4
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    ?
_cell_measurement_theta_min      ?
_cell_measurement_theta_max      ?

_exptl_crystal_description       block
_exptl_crystal_colour            ?
_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.2
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.777
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             992
_exptl_absorpt_coefficient_mu    1.224
_exptl_absorpt_correction_type   ?
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   ?

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      293(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  ?
_diffrn_measurement_method       ?
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            8900
_diffrn_reflns_av_R_equivalents  0.0180
_diffrn_reflns_av_sigmaI/netI    0.0137
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_k_min       -47
_diffrn_reflns_limit_k_max       45
_diffrn_reflns_limit_l_min       -9
_diffrn_reflns_limit_l_max       6
_diffrn_reflns_theta_min         1.00
_diffrn_reflns_theta_max         25.01
_reflns_number_total             1656
_reflns_number_gt                1620
_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)+(0.1082P)²+2.3823P] 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     SHELXL
_refine_ls_extinction_coef       0.0184(17)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_number_reflns         1656
_refine_ls_number_parameters     145
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0361
_refine_ls_R_factor_gt           0.0326
_refine_ls_wR_factor_ref         0.1329
_refine_ls_wR_factor_gt          0.1243
_refine_ls_goodness_of_fit_ref   1.070
_refine_ls_restrained_S_all      1.071
_refine_ls_shift/su_max          0.020
_refine_ls_shift/su_mean         0.003

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
Cd1 Cd 0.22106(8) 0.2500 0.06446(4) 0.0212(3) Uani 1 2 d SU . .
O1 O 0.0741(12) 0.2500 -0.1997(6) 0.0511(15) Uani 1 2 d S . .
O2 O 0.3299(8) 0.2500 0.3525(6) 0.0248(9) Uani 1 2 d S . .
O3 O 0.5199(6) 0.28878(7) -0.0136(4) 0.0348(7) Uani 1 1 d U . .
O5 O 0.1952(7) 0.19334(10) 0.0958(5) 0.0421(9) Uani 1 1 d . . .
O6 O 0.7430(6) 0.05847(10) -0.0127(7) 0.0451(9) Uani 1 1 d . . .
C C 0.3924(8) 0.18800(9) 0.0372(5) 0.0267(9) Uani 1 1 d . . .
C11 C 0.6869(10) 0.14669(13) -0.0595(5) 0.0361(12) Uani 1 1 d . . .
H11 H 0.7740 0.1639 -0.1039 0.043 Uiso 1 1 calc R . .
C13 C 0.4054(10) 0.02597(11) -0.0918(6) 0.0393(11) Uani 1 1 d . . .
H13 H 0.3429 0.0434 -0.1528 0.047 Uiso 1 1 calc R . .
C14 C 0.3548(9) 0.12760(11) 0.0911(5) 0.0320(9) Uani 1 1 d . . .
H14 H 0.2159 0.1319 0.1458 0.038 Uiso 1 1 calc R . .
C16 C 0.4343(10) 0.09537(11) 0.0814(5) 0.0365(11) Uani 1 1 d . . .
H16 H 0.3514 0.0782 0.1305 0.044 Uiso 1 1 calc R . .
C17 C 0.6404(8) 0.08919(9) -0.0032(6) 0.0312(9) Uani 1 1 d . . .
C22 C 0.4782(8) 0.15340(9) 0.0209(5) 0.0286(9) Uani 1 1 d . . .
C25 C 0.7661(9) 0.11460(16) -0.0741(6) 0.0377(14) Uani 1 1 d . . .
H25 H 0.9030 0.1102 -0.1312 0.045 Uiso 1 1 calc R . .
C26 C 0.7053(9) 0.00426(15) 0.0873(7) 0.0376(12) Uani 1 1 d . . .
H26 H 0.8430 0.0073 0.1458 0.045 Uiso 1 1 calc R . .
C27 C 0.6109(8) 0.02978(10) -0.0041(6) 0.0336(9) Uani 1 1 d . . .
H30 H 0.283(8) 0.2627(14) 0.398(7) 0.018(13) Uiso 1 1 d . . .
H1 H 0.060(16) 0.263(2) -0.257(9) 0.10(3) Uiso 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
Cd1 O1 2.255(5) . ?
Cd1 O5 2.316(4) 8_565 ?
Cd1 O5 2.316(4) . ?
Cd1 O2 2.358(4) 6_556 ?
Cd1 O2 2.362(4) . ?
Cd1 O3 2.419(3) . ?
Cd1 O3 2.419(3) 8_565 ?
Cd1 C 2.712(4) 8_565 ?
Cd1 C 2.712(4) . ?
O1 H1 0.71(8) . ?
O2 Cd1 2.358(4) 6_656 ?
O2 H30 0.68(5) . ?
O3 C 1.262(5) 8_565 ?
O5 C 1.251(7) . ?
O6 C17 1.383(6) . ?
O6 C27 1.394(6) . ?
C O3 1.262(5) 8_565 ?
C C22 1.494(5) . ?
C11 C25 1.385(9) . ?
C11 C22 1.393(7) . ?
C11 H11 0.9300 . ?
C13 C26 1.384(8) 5_655 ?
C13 C27 1.386(7) . ?
C13 H13 0.9300 . ?
C14 C16 1.388(6) . ?
C14 C22 1.383(6) . ?
C14 H14 0.9300 . ?
C16 C17 1.391(7) . ?
C16 H16 0.9300 . ?
C17 C25 1.381(7) . ?
C25 H25 0.9300 . ?
C26 C27 1.376(7) . ?
C26 C13 1.384(8) 5_655 ?
C26 H26 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 Cd1 O5 94.28(10) . 8_565 ?
O1 Cd1 O5 94.28(10) . . ?
O5 Cd1 O5 165.6(2) 8_565 . ?
O1 Cd1 O2 84.0(2) . 6_556 ?
O5 Cd1 O2 84.73(10) 8_565 6_556 ?
O5 Cd1 O2 84.73(10) . 6_556 ?
O1 Cd1 O2 173.3(2) . . ?
O5 Cd1 O2 85.08(10) 8_565 . ?
O5 Cd1 O2 85.08(11) . . ?
O2 Cd1 O2 89.32(10) 6_556 . ?
O1 Cd1 O3 91.96(15) . . ?
O5 Cd1 O3 55.12(12) 8_565 . ?
O5 Cd1 O3 135.96(12) . . ?
O2 Cd1 O3 139.31(7) 6_556 . ?
O2 Cd1 O3 93.13(11) . . ?
O1 Cd1 O3 91.96(15) . 8_565 ?
O5 Cd1 O3 135.96(12) 8_565 8_565 ?
O5 Cd1 O3 55.12(12) . 8_565 ?
O2 Cd1 O3 139.31(7) 6_556 8_565 ?
O2 Cd1 O3 93.13(11) . 8_565 ?
O3 Cd1 O3 81.15(14) . 8_565 ?
O1 Cd1 C 93.70(11) . 8_565 ?
O5 Cd1 C 27.40(15) 8_565 8_565 ?
O5 Cd1 C 162.20(13) . 8_565 ?
O2 Cd1 C 111.93(10) 6_556 8_565 ?
O2 Cd1 C 88.80(9) . 8_565 ?
O3 Cd1 C 27.73(12) . 8_565 ?
O3 Cd1 C 108.73(12) 8_565 8_565 ?
O1 Cd1 C 93.70(11) . . ?
O5 Cd1 C 162.20(13) 8_565 . ?
O5 Cd1 C 27.40(15) . . ?
O2 Cd1 C 111.93(10) 6_556 . ?
O2 Cd1 C 88.80(9) . . ?
O3 Cd1 C 108.73(12) . . ?
O3 Cd1 C 27.73(12) 8_565 . ?
C Cd1 C 136.0(2) 8_565 . ?
Cd1 O1 H1 129(7) . . ?
Cd1 O2 Cd1 121.65(19) 6_656 . ?
Cd1 O2 H30 103(4) 6_656 . ?
Cd1 O2 H30 114(5) . . ?
C O3 Cd1 89.2(3) 8_565 . ?
C O5 Cd1 94.2(3) . . ?
C17 O6 C27 120.9(3) . . ?
O5 C O3 121.5(4) . 8_565 ?
O5 C C22 119.8(4) . . ?
O3 C C22 118.6(4) 8_565 . ?
O5 C Cd1 58.4(2) . . ?
O3 C Cd1 63.1(2) 8_565 . ?
C22 C Cd1 177.9(3) . . ?
C25 C11 C22 120.6(5) . . ?
C25 C11 H11 119.7 . . ?
C22 C11 H11 119.7 . . ?
C26 C13 C27 118.9(4) 5_655 . ?
C26 C13 H13 120.5 5_655 . ?
C27 C13 H13 120.5 . . ?
C16 C14 C22 121.3(5) . . ?
C16 C14 H14 119.4 . . ?
C22 C14 H14 119.4 . . ?
C14 C16 C17 118.8(4) . . ?
C14 C16 H16 120.6 . . ?
C17 C16 H16 120.6 . . ?
C25 C17 O6 115.1(4) . . ?
C25 C17 C16 120.9(4) . . ?
O6 C17 C16 123.9(4) . . ?
C14 C22 C11 118.9(4) . . ?
C14 C22 C 120.3(4) . . ?
C11 C22 C 120.8(4) . . ?
C17 C25 C11 119.6(5) . . ?
C17 C25 H25 120.2 . . ?
C11 C25 H25 120.2 . . ?
C27 C26 C13 119.8(5) . 5_655 ?
C27 C26 H26 120.1 . . ?
C13 C26 H26 120.1 5_655 . ?
C26 C27 C13 121.3(4) . . ?
C26 C27 O6 115.8(4) . . ?
C13 C27 O6 122.7(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
O1 Cd1 O2 Cd1 180.0 . . . 6_656 ?
O5 Cd1 O2 Cd1 -95.23(10) 8_565 . . 6_656 ?
O5 Cd1 O2 Cd1 95.23(10) . . . 6_656 ?
O2 Cd1 O2 Cd1 180.0 6_556 . . 6_656 ?
O3 Cd1 O2 Cd1 -40.65(7) . . . 6_656 ?
O3 Cd1 O2 Cd1 40.65(7) 8_565 . . 6_656 ?
C Cd1 O2 Cd1 -68.04(10) 8_565 . . 6_656 ?
C Cd1 O2 Cd1 68.04(10) . . . 6_656 ?
O1 Cd1 O3 C 94.2(3) . . . 8_565 ?
O5 Cd1 O3 C 0.4(2) 8_565 . . 8_565 ?
O5 Cd1 O3 C -167.6(2) . . . 8_565 ?
O2 Cd1 O3 C 11.2(3) 6_556 . . 8_565 ?
O2 Cd1 O3 C -81.4(2) . . . 8_565 ?
O3 Cd1 O3 C -174.10(19) 8_565 . . 8_565 ?
C Cd1 O3 C -171.2(3) . . . 8_565 ?
O1 Cd1 O5 C 89.8(3) . . . . ?
O5 Cd1 O5 C -143.8(6) 8_565 . . . ?
O2 Cd1 O5 C 173.3(3) 6_556 . . . ?
O2 Cd1 O5 C -96.9(3) . . . . ?
O3 Cd1 O5 C -7.5(4) . . . . ?
O3 Cd1 O5 C 0.4(2) 8_565 . . . ?
C Cd1 O5 C -26.6(5) 8_565 . . . ?
Cd1 O5 C O3 -0.7(5) . . . 8_565 ?
Cd1 O5 C C22 -178.7(3) . . . . ?
O1 Cd1 C O5 -92.2(3) . . . . ?
O5 Cd1 C O5 151.3(6) 8_565 . . . ?
O2 Cd1 C O5 -7.2(3) 6_556 . . . ?
O2 Cd1 C O5 81.6(3) . . . . ?
O3 Cd1 C O5 174.5(3) . . . . ?
O3 Cd1 C O5 -179.3(4) 8_565 . . . ?
C Cd1 C O5 168.6(2) 8_565 . . . ?
O1 Cd1 C O3 87.2(3) . . . 8_565 ?
O5 Cd1 C O3 -29.3(5) 8_565 . . 8_565 ?
O5 Cd1 C O3 179.3(4) . . . 8_565 ?
O2 Cd1 C O3 172.2(2) 6_556 . . 8_565 ?
O2 Cd1 C O3 -99.1(2) . . . 8_565 ?
O3 Cd1 C O3 -6.2(2) . . . 8_565 ?
C Cd1 C O3 -12.0(4) 8_565 . . 8_565 ?
O1 Cd1 C C22 -59(8) . . . . ?
O5 Cd1 C C22 -176(8) 8_565 . . . ?
O5 Cd1 C C22 33(8) . . . . ?
O2 Cd1 C C22 26(8) 6_556 . . . ?
O2 Cd1 C C22 115(8) . . . . ?
O3 Cd1 C C22 -153(8) . . . . ?
O3 Cd1 C C22 -146(8) 8_565 . . . ?
C Cd1 C C22 -158(8) 8_565 . . . ?
C22 C14 C16 C17 -1.0(7) . . . . ?
C27 O6 C17 C25 -156.8(5) . . . . ?
C27 O6 C17 C16 27.8(8) . . . . ?
C14 C16 C17 C25 1.1(7) . . . . ?
C14 C16 C17 O6 176.1(5) . . . . ?
C16 C14 C22 C11 -0.5(7) . . . . ?
C16 C14 C22 C -178.3(4) . . . . ?
C25 C11 C22 C14 2.1(7) . . . . ?
C25 C11 C22 C 179.9(4) . . . . ?
O5 C C22 C14 -8.8(6) . . . . ?
O3 C C22 C14 173.1(4) 8_565 . . . ?
Cd1 C C22 C14 -41(8) . . . . ?
O5 C C22 C11 173.5(4) . . . . ?
O3 C C22 C11 -4.6(6) 8_565 . . . ?
Cd1 C C22 C11 141(8) . . . . ?
O6 C17 C25 C11 -175.0(5) . . . . ?
C16 C17 C25 C11 0.5(7) . . . . ?
C22 C11 C25 C17 -2.1(7) . . . . ?
C13 C26 C27 C13 0.3(9) 5_655 . . . ?
C13 C26 C27 O6 -175.1(5) 5_655 . . . ?
C26 C13 C27 C26 -0.3(8) 5_655 . . . ?
C26 C13 C27 O6 174.8(5) 5_655 . . . ?
C17 O6 C27 C26 -140.6(5) . . . . ?
C17 O6 C27 C13 44.1(8) . . . . ?

_diffrn_measured_fraction_theta_max 0.993
_diffrn_reflns_theta_full        25.01
_diffrn_measured_fraction_theta_full 0.993
_refine_diff_density_max         1.165
_refine_diff_density_min         -0.718
_refine_diff_density_rms         0.202
####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_3
_database_code_depnum_ccdc_archive 'CCDC 1053480'
_audit_update_record             
;
2015-03-12 deposited with the CCDC.
2015-05-13 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C20 H16 Co O8'
_chemical_formula_weight         443.26

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'
Co Co 0.3494 0.9721 '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           orthorhombic
_symmetry_space_group_name_H-M   Pnma

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

_cell_length_a                   5.6453(13)
_cell_length_b                   40.200(9)
_cell_length_c                   7.6789(19)
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_volume                     1742.7(7)
_cell_formula_units_Z            4
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    ?
_cell_measurement_theta_min      ?
_cell_measurement_theta_max      ?

_exptl_crystal_description       sheet
_exptl_crystal_colour            ?
_exptl_crystal_size_max          ?
_exptl_crystal_size_mid          ?
_exptl_crystal_size_min          ?
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.689
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             908
_exptl_absorpt_coefficient_mu    1.035
_exptl_absorpt_correction_type   ?
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   ?

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      293(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  ?
_diffrn_measurement_method       ?
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            9652
_diffrn_reflns_av_R_equivalents  0.0497
_diffrn_reflns_av_sigmaI/netI    0.0521
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_k_min       -53
_diffrn_reflns_limit_k_max       46
_diffrn_reflns_limit_l_min       -7
_diffrn_reflns_limit_l_max       10
_diffrn_reflns_theta_min         2.03
_diffrn_reflns_theta_max         28.38
_reflns_number_total             2215
_reflns_number_gt                1762
_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)+(0.0337P)²+1.1365P] 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         2211
_refine_ls_number_parameters     168
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0590
_refine_ls_R_factor_gt           0.0380
_refine_ls_wR_factor_ref         0.0868
_refine_ls_wR_factor_gt          0.0813
_refine_ls_goodness_of_fit_ref   1.067
_refine_ls_restrained_S_all      1.067
_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
Co1 Co 0.24110(7) 0.2500 0.42955(5) 0.01710(12) Uani 1 2 d S . .
O1 O 0.6144(4) 0.2500 0.3383(3) 0.0178(4) Uani 1 2 d S . .
O2 O -0.2508(3) 0.05899(4) 0.5086(3) 0.0339(4) Uani 1 1 d . . .
O3 O -0.0504(3) 0.21400(4) 0.5136(2) 0.0331(4) Uani 1 1 d . . .
O4 O 0.2861(3) 0.19751(4) 0.4036(2) 0.0361(4) Uani 1 1 d . . .
O5 O 0.3817(5) 0.2500 0.6788(3) 0.0346(6) Uani 1 2 d S . .
C1 C -0.1487(4) 0.09026(5) 0.5021(3) 0.0235(4) Uani 1 1 d . . .
C2 C 0.0042(4) 0.15550(5) 0.4808(3) 0.0215(4) Uani 1 1 d . . .
C3 C 0.0850(4) 0.19064(5) 0.4643(3) 0.0250(5) Uani 1 1 d . . .
C4 C -0.1129(4) 0.03040(5) 0.5011(3) 0.0248(5) Uani 1 1 d . . .
C5 C 0.0622(4) 0.09722(5) 0.4183(3) 0.0257(5) Uani 1 1 d . . .
C6 C -0.2078(4) 0.14794(5) 0.5623(3) 0.0273(5) Uani 1 1 d . . .
C7 C 0.0998(4) 0.02673(5) 0.5881(3) 0.0273(5) Uani 1 1 d . . .
C8 C 0.1385(4) 0.13000(5) 0.4103(3) 0.0243(5) Uani 1 1 d . . .
C9 C -0.2850(4) 0.11534(6) 0.5754(3) 0.0280(5) Uani 1 1 d . . .
C10 C -0.2121(4) 0.00383(5) 0.4129(3) 0.0265(5) Uani 1 1 d . . .
H2 H -0.354(5) 0.0072(6) 0.353(3) 0.029(6) Uiso 1 1 d . . .
H4 H 0.152(5) 0.0799(6) 0.364(3) 0.037(7) Uiso 1 1 d . . .
H5 H 0.274(4) 0.1346(6) 0.351(3) 0.025(6) Uiso 1 1 d . . .
H1 H 0.165(5) 0.0444(6) 0.652(3) 0.036(7) Uiso 1 1 d . . .
H3 H -0.428(5) 0.1100(6) 0.631(3) 0.033(7) Uiso 1 1 d . . .
H8 H 0.679(5) 0.2660(6) 0.378(3) 0.033(7) Uiso 1 1 d . . .
H7 H 0.380(6) 0.2638(7) 0.737(4) 0.063(11) Uiso 1 1 d . . .
H6 H -0.311(5) 0.1652(7) 0.607(4) 0.048(8) Uiso 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
Co1 O5 2.072(3) . ?
Co1 O4 2.1348(17) . ?
Co1 O4 2.1348(17) 8_565 ?
Co1 O1 2.178(2) 6_556 ?
Co1 O1 2.221(2) . ?
Co1 O3 2.2846(18) . ?
Co1 O3 2.2846(18) 8_565 ?
O1 Co1 2.178(2) 6_656 ?
O1 H8 0.80(2) . ?
O2 C1 1.384(2) . ?
O2 C4 1.389(3) . ?
O3 C3 1.269(3) . ?
O4 C3 1.258(3) . ?
O5 H7 0.71(3) . ?
C1 C5 1.382(3) . ?
C1 C9 1.388(3) . ?
C2 C6 1.384(3) . ?
C2 C8 1.385(3) . ?
C2 C3 1.490(3) . ?
C4 C7 1.382(3) . ?
C4 C10 1.383(3) . ?
C5 C8 1.388(3) . ?
C5 H4 0.96(3) . ?
C6 C9 1.385(3) . ?
C6 H6 0.97(3) . ?
C7 C10 1.382(3) 5_556 ?
C7 H1 0.94(3) . ?
C8 H5 0.91(2) . ?
C9 H3 0.94(3) . ?
C10 C7 1.382(3) 5_556 ?
C10 H2 0.93(3) . ?

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
O5 Co1 O4 92.33(5) . . ?
O5 Co1 O4 92.33(5) . 8_565 ?
O4 Co1 O4 162.60(10) . 8_565 ?
O5 Co1 O1 176.64(10) . 6_556 ?
O4 Co1 O1 87.18(5) . 6_556 ?
O4 Co1 O1 87.18(5) 8_565 6_556 ?
O5 Co1 O1 85.86(10) . . ?
O4 Co1 O1 81.81(5) . . ?
O4 Co1 O1 81.81(5) 8_565 . ?
O1 Co1 O1 90.78(5) 6_556 . ?
O5 Co1 O3 90.87(8) . . ?
O4 Co1 O3 59.07(6) . . ?
O4 Co1 O3 137.59(6) 8_565 . ?
O1 Co1 O3 91.72(6) 6_556 . ?
O1 Co1 O3 140.60(4) . . ?
O5 Co1 O3 90.87(8) . 8_565 ?
O4 Co1 O3 137.59(6) . 8_565 ?
O4 Co1 O3 59.07(6) 8_565 8_565 ?
O1 Co1 O3 91.72(6) 6_556 8_565 ?
O1 Co1 O3 140.60(4) . 8_565 ?
O3 Co1 O3 78.61(8) . 8_565 ?
Co1 O1 Co1 127.56(10) 6_656 . ?
Co1 O1 H8 101.9(19) 6_656 . ?
Co1 O1 H8 108.4(19) . . ?
C1 O2 C4 121.08(18) . . ?
C3 O3 Co1 87.16(14) . . ?
C3 O4 Co1 94.29(13) . . ?
Co1 O5 H7 125(3) . . ?
C5 C1 O2 124.0(2) . . ?
C5 C1 C9 121.31(19) . . ?
O2 C1 C9 114.5(2) . . ?
C6 C2 C8 119.16(19) . . ?
C6 C2 C3 120.77(19) . . ?
C8 C2 C3 120.1(2) . . ?
O4 C3 O3 119.5(2) . . ?
O4 C3 C2 121.1(2) . . ?
O3 C3 C2 119.4(2) . . ?
C7 C4 C10 120.4(2) . . ?
C7 C4 O2 123.7(2) . . ?
C10 C4 O2 115.6(2) . . ?
C1 C5 C8 118.7(2) . . ?
C1 C5 H4 120.8(16) . . ?
C8 C5 H4 120.5(16) . . ?
C2 C6 C9 120.9(2) . . ?
C2 C6 H6 121.6(17) . . ?
C9 C6 H6 117.4(17) . . ?
C4 C7 C10 119.4(2) . 5_556 ?
C4 C7 H1 120.9(16) . . ?
C10 C7 H1 119.6(16) 5_556 . ?
C2 C8 C5 121.1(2) . . ?
C2 C8 H5 120.3(14) . . ?
C5 C8 H5 118.5(14) . . ?
C6 C9 C1 118.9(2) . . ?
C6 C9 H3 121.4(15) . . ?
C1 C9 H3 119.6(15) . . ?
C7 C10 C4 120.2(2) 5_556 . ?
C7 C10 H2 121.3(14) 5_556 . ?
C4 C10 H2 118.4(14) . . ?

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
O5 Co1 O1 Co1 180.0 . . . 6_656 ?
O4 Co1 O1 Co1 87.04(5) . . . 6_656 ?
O4 Co1 O1 Co1 -87.04(5) 8_565 . . 6_656 ?
O1 Co1 O1 Co1 0.0 6_556 . . 6_656 ?
O3 Co1 O1 Co1 93.67(9) . . . 6_656 ?
O3 Co1 O1 Co1 -93.67(9) 8_565 . . 6_656 ?
O5 Co1 O3 C3 -92.59(13) . . . . ?
O4 Co1 O3 C3 -0.39(12) . . . . ?
O4 Co1 O3 C3 173.00(12) 8_565 . . . ?
O1 Co1 O3 C3 85.29(12) 6_556 . . . ?
O1 Co1 O3 C3 -8.05(18) . . . . ?
O3 Co1 O3 C3 176.70(10) 8_565 . . . ?
O5 Co1 O4 C3 90.02(15) . . . . ?
O4 Co1 O4 C3 -164.6(2) 8_565 . . . ?
O1 Co1 O4 C3 -93.31(14) 6_556 . . . ?
O1 Co1 O4 C3 175.50(14) . . . . ?
O3 Co1 O4 C3 0.40(12) . . . . ?
O3 Co1 O4 C3 -3.84(18) 8_565 . . . ?
C4 O2 C1 C5 28.5(3) . . . . ?
C4 O2 C1 C9 -156.5(2) . . . . ?
Co1 O4 C3 O3 -0.7(2) . . . . ?
Co1 O4 C3 C2 179.85(17) . . . . ?
Co1 O3 C3 O4 0.7(2) . . . . ?
Co1 O3 C3 C2 -179.89(17) . . . . ?
C6 C2 C3 O4 174.0(2) . . . . ?
C8 C2 C3 O4 -7.7(3) . . . . ?
C6 C2 C3 O3 -5.4(3) . . . . ?
C8 C2 C3 O3 172.9(2) . . . . ?
C1 O2 C4 C7 41.4(3) . . . . ?
C1 O2 C4 C10 -144.6(2) . . . . ?
O2 C1 C5 C8 175.5(2) . . . . ?
C9 C1 C5 C8 0.8(3) . . . . ?
C8 C2 C6 C9 0.7(3) . . . . ?
C3 C2 C6 C9 179.0(2) . . . . ?
C10 C4 C7 C10 -0.4(4) . . . 5_556 ?
O2 C4 C7 C10 173.3(2) . . . 5_556 ?
C6 C2 C8 C5 0.8(3) . . . . ?
C3 C2 C8 C5 -177.5(2) . . . . ?
C1 C5 C8 C2 -1.5(3) . . . . ?
C2 C6 C9 C1 -1.4(3) . . . . ?
C5 C1 C9 C6 0.6(3) . . . . ?
O2 C1 C9 C6 -174.6(2) . . . . ?
C7 C4 C10 C7 0.4(4) . . . 5_556 ?
O2 C4 C10 C7 -173.8(2) . . . 5_556 ?

_diffrn_measured_fraction_theta_max 0.998
_diffrn_reflns_theta_full        28.38
_diffrn_measured_fraction_theta_full 0.998
_refine_diff_density_max         0.511
_refine_diff_density_min         -0.496
_refine_diff_density_rms         0.079
####################################################################### 
# 
# 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_6a
_database_code_depnum_ccdc_archive 'CCDC 1053484'
_audit_update_record             
;
2015-03-12 deposited with the CCDC.
2015-05-13 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C26 H17 Cu N O6'
_chemical_formula_weight         502.95

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cu Cu -1.9646 0.5888 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.0180 '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

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

_cell_length_a                   10.6053(8)
_cell_length_b                   11.1058(13)
_cell_length_c                   12.1321(17)
_cell_angle_alpha                114.559(13)
_cell_angle_beta                 111.070(10)
_cell_angle_gamma                96.515(8)
_cell_volume                     1153.1(2)
_cell_formula_units_Z            2
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    1647
_cell_measurement_theta_min      4.4840
_cell_measurement_theta_max      70.4440

_exptl_crystal_description       block
_exptl_crystal_colour            blue
_exptl_crystal_size_max          0.09
_exptl_crystal_size_mid          0.08
_exptl_crystal_size_min          0.07
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.449
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             514
_exptl_absorpt_coefficient_mu    1.702
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.8619
_exptl_absorpt_correction_T_max  0.8901
_exptl_absorpt_process_details   sadabs

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      293(2)
_diffrn_radiation_wavelength     1.54184
_diffrn_radiation_type           CuK\a
_diffrn_radiation_source         'Enhance (Cu) X-ray Source'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Xcalibur, Eos, Gemini'
_diffrn_measurement_method       ?
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            6798
_diffrn_reflns_av_R_equivalents  0.0451
_diffrn_reflns_av_sigmaI/netI    0.0752
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_theta_min         4.49
_diffrn_reflns_theta_max         67.25
_reflns_number_total             4129
_reflns_number_gt                3037
_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)+(0.0446P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         4129
_refine_ls_number_parameters     307
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0741
_refine_ls_R_factor_gt           0.0500
_refine_ls_wR_factor_ref         0.1237
_refine_ls_wR_factor_gt          0.1089
_refine_ls_goodness_of_fit_ref   1.014
_refine_ls_restrained_S_all      1.014
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
Cu1 Cu 1.10227(5) 0.44337(5) 0.49679(6) 0.03175(16) Uani 1 1 d . . .
N1 N 1.2450(3) 0.3167(3) 0.4950(3) 0.0386(7) Uani 1 1 d . . .
O1 O 0.9358(3) 0.2807(3) 0.3576(3) 0.0448(7) Uani 1 1 d . . .
O2 O 0.7594(3) 0.3728(2) 0.3643(3) 0.0422(6) Uani 1 1 d . . .
O3 O 0.4166(3) -0.2696(3) 0.0156(3) 0.0572(8) Uani 1 1 d . . .
O4 O 1.0676(3) 0.4149(3) 0.6344(3) 0.0438(7) Uani 1 1 d . . .
O5 O 0.8912(3) 0.5069(3) 0.6393(3) 0.0421(6) Uani 1 1 d . . .
O6 O 0.8843(3) 0.2046(3) 0.9797(3) 0.0562(8) Uani 1 1 d . . .
C1 C 0.8067(4) 0.2715(4) 0.3253(4) 0.0375(9) Uani 1 1 d . . .
C2 C 0.7030(4) 0.1280(4) 0.2372(4) 0.0392(9) Uani 1 1 d . . .
C3 C 0.7509(4) 0.0141(4) 0.1960(5) 0.0555(12) Uani 1 1 d . . .
H3 H 0.8468 0.0280 0.2178 0.067 Uiso 1 1 calc R . .
C4 C 0.6589(4) -0.1197(4) 0.1232(5) 0.0637(14) Uani 1 1 d . . .
H4 H 0.6926 -0.1955 0.0971 0.076 Uiso 1 1 calc R . .
C5 C 0.5160(4) -0.1403(4) 0.0893(4) 0.0472(10) Uani 1 1 d . . .
C6 C 0.4654(4) -0.0283(4) 0.1259(4) 0.0451(10) Uani 1 1 d . . .
H6 H 0.3690 -0.0422 0.1013 0.054 Uiso 1 1 calc R . .
C7 C 0.5592(4) 0.1049(4) 0.1995(4) 0.0437(10) Uani 1 1 d . . .
H7 H 0.5251 0.1806 0.2241 0.052 Uiso 1 1 calc R . .
C8 C 0.4627(4) -0.3839(4) 0.0093(4) 0.0454(10) Uani 1 1 d . . .
C9 C 0.5301(5) -0.3927(4) 0.1240(5) 0.0604(12) Uani 1 1 d . . .
H9 H 0.5494 -0.3198 0.2081 0.073 Uiso 1 1 calc R . .
C10 C 0.4301(5) -0.4901(5) -0.1154(5) 0.0560(11) Uani 1 1 d . . .
H10 H 0.3822 -0.4844 -0.1932 0.067 Uiso 1 1 calc R . .
C11 C 0.9727(4) 0.4412(4) 0.6717(4) 0.0399(9) Uani 1 1 d . . .
C12 C 0.9543(4) 0.3835(4) 0.7582(4) 0.0406(9) Uani 1 1 d . . .
C13 C 1.0341(5) 0.3014(5) 0.7877(5) 0.0539(12) Uani 1 1 d . . .
H13 H 1.1035 0.2876 0.7581 0.065 Uiso 1 1 calc R . .
C14 C 1.0132(5) 0.2390(5) 0.8605(5) 0.0555(12) Uani 1 1 d . . .
H14 H 1.0670 0.1829 0.8784 0.067 Uiso 1 1 calc R . .
C15 C 0.9120(4) 0.2612(4) 0.9058(4) 0.0443(10) Uani 1 1 d . . .
C16 C 0.8329(4) 0.3462(4) 0.8812(4) 0.0439(10) Uani 1 1 d . . .
H16 H 0.7658 0.3622 0.9138 0.053 Uiso 1 1 calc R . .
C17 C 0.8544(4) 0.4070(4) 0.8079(4) 0.0432(10) Uani 1 1 d . . .
H17 H 0.8016 0.4644 0.7915 0.052 Uiso 1 1 calc R . .
C18 C 0.9447(4) 0.1015(4) 0.9889(4) 0.0431(10) Uani 1 1 d . . .
C19 C 1.0544(5) 0.1345(5) 1.1095(5) 0.0536(11) Uani 1 1 d . . .
H19 H 1.0904 0.2243 1.1830 0.064 Uiso 1 1 calc R . .
C20 C 0.8890(5) -0.0308(5) 0.8801(5) 0.0534(11) Uani 1 1 d . . .
H20 H 0.8134 -0.0511 0.7994 0.064 Uiso 1 1 calc R . .
C21 C 1.2036(4) 0.1960(4) 0.4898(5) 0.0489(10) Uani 1 1 d . . .
H21 H 1.1151 0.1695 0.4859 0.059 Uiso 1 1 calc R . .
C22 C 1.2861(5) 0.1083(5) 0.4899(5) 0.0649(14) Uani 1 1 d . . .
H22 H 1.2524 0.0241 0.4847 0.078 Uiso 1 1 calc R . .
C23 C 1.4200(5) 0.1468(5) 0.4979(6) 0.0683(14) Uani 1 1 d . . .
C24 C 1.4612(5) 0.2714(5) 0.5032(6) 0.0710(15) Uani 1 1 d . . .
H24 H 1.5494 0.3017 0.5079 0.085 Uiso 1 1 calc R . .
C25 C 1.3719(5) 0.3509(4) 0.5016(5) 0.0559(12) Uani 1 1 d . . .
H25 H 1.4027 0.4351 0.5055 0.067 Uiso 1 1 calc R . .
C26 C 1.5177(7) 0.0572(7) 0.5000(10) 0.132(3) Uani 1 1 d . . .
H26 H 1.6044 0.0854 0.5012 0.158 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 1.957(3) . ?
Cu1 O2 1.960(2) 2_766 ?
Cu1 O5 1.967(2) 2_766 ?
Cu1 O4 1.969(2) . ?
Cu1 N1 2.180(3) . ?
Cu1 Cu1 2.6368(10) 2_766 ?
N1 C25 1.320(5) . ?
N1 C21 1.330(5) . ?
O1 C1 1.260(4) . ?
O2 C1 1.264(4) . ?
O2 Cu1 1.960(2) 2_766 ?
O3 C5 1.372(4) . ?
O3 C8 1.394(5) . ?
O4 C11 1.259(4) . ?
O5 C11 1.254(4) . ?
O5 Cu1 1.967(2) 2_766 ?
O6 C15 1.378(4) . ?
O6 C18 1.398(4) . ?
C1 C2 1.495(5) . ?
C2 C3 1.381(5) . ?
C2 C7 1.383(5) . ?
C3 C4 1.379(5) . ?
C4 C5 1.383(5) . ?
C5 C6 1.377(5) . ?
C6 C7 1.380(5) . ?
C8 C10 1.359(6) . ?
C8 C9 1.368(6) . ?
C9 C10 1.388(6) 2_645 ?
C10 C9 1.388(6) 2_645 ?
C11 C12 1.493(5) . ?
C12 C13 1.380(5) . ?
C12 C17 1.395(5) . ?
C13 C14 1.387(5) . ?
C14 C15 1.373(5) . ?
C15 C16 1.386(5) . ?
C16 C17 1.382(5) . ?
C18 C19 1.365(6) . ?
C18 C20 1.371(6) . ?
C19 C20 1.388(6) 2_757 ?
C20 C19 1.388(6) 2_757 ?
C21 C22 1.381(5) . ?
C22 C23 1.392(6) . ?
C23 C24 1.371(6) . ?
C23 C26 1.517(6) . ?
C24 C25 1.367(6) . ?
C26 C26 1.283(11) 2_856 ?

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 O2 168.27(11) . 2_766 ?
O1 Cu1 O5 90.98(12) . 2_766 ?
O2 Cu1 O5 87.33(11) 2_766 2_766 ?
O1 Cu1 O4 88.04(12) . . ?
O2 Cu1 O4 91.26(12) 2_766 . ?
O5 Cu1 O4 168.28(10) 2_766 . ?
O1 Cu1 N1 92.20(11) . . ?
O2 Cu1 N1 99.52(11) 2_766 . ?
O5 Cu1 N1 100.49(11) 2_766 . ?
O4 Cu1 N1 91.22(11) . . ?
O1 Cu1 Cu1 79.87(8) . 2_766 ?
O2 Cu1 Cu1 88.49(8) 2_766 2_766 ?
O5 Cu1 Cu1 88.93(8) 2_766 2_766 ?
O4 Cu1 Cu1 79.40(8) . 2_766 ?
N1 Cu1 Cu1 167.85(8) . 2_766 ?
C25 N1 C21 116.5(3) . . ?
C25 N1 Cu1 125.4(3) . . ?
C21 N1 Cu1 118.1(3) . . ?
C1 O1 Cu1 128.0(3) . . ?
C1 O2 Cu1 117.7(2) . 2_766 ?
C5 O3 C8 118.5(3) . . ?
C11 O4 Cu1 128.1(2) . . ?
C11 O5 Cu1 117.2(2) . 2_766 ?
C15 O6 C18 117.8(3) . . ?
O1 C1 O2 125.3(3) . . ?
O1 C1 C2 116.5(3) . . ?
O2 C1 C2 118.1(3) . . ?
C3 C2 C7 118.5(3) . . ?
C3 C2 C1 119.9(3) . . ?
C7 C2 C1 121.6(3) . . ?
C4 C3 C2 121.1(4) . . ?
C3 C4 C5 119.4(4) . . ?
O3 C5 C6 116.2(3) . . ?
O3 C5 C4 123.4(4) . . ?
C6 C5 C4 120.4(4) . . ?
C5 C6 C7 119.4(4) . . ?
C6 C7 C2 121.2(4) . . ?
C10 C8 C9 121.1(4) . . ?
C10 C8 O3 117.7(4) . . ?
C9 C8 O3 121.0(4) . . ?
C8 C9 C10 120.3(4) . 2_645 ?
C8 C10 C9 118.5(4) . 2_645 ?
O5 C11 O4 126.0(3) . . ?
O5 C11 C12 118.1(3) . . ?
O4 C11 C12 115.9(3) . . ?
C13 C12 C17 118.2(3) . . ?
C13 C12 C11 120.1(4) . . ?
C17 C12 C11 121.6(3) . . ?
C12 C13 C14 121.6(4) . . ?
C15 C14 C13 119.1(4) . . ?
C14 C15 O6 123.4(3) . . ?
C14 C15 C16 120.8(4) . . ?
O6 C15 C16 115.9(3) . . ?
C17 C16 C15 119.4(4) . . ?
C16 C17 C12 120.8(3) . . ?
C19 C18 C20 121.6(4) . . ?
C19 C18 O6 118.5(4) . . ?
C20 C18 O6 119.9(4) . . ?
C18 C19 C20 118.4(4) . 2_757 ?
C18 C20 C19 120.0(4) . 2_757 ?
N1 C21 C22 123.1(4) . . ?
C21 C22 C23 119.5(4) . . ?
C24 C23 C22 116.8(4) . . ?
C24 C23 C26 120.4(5) . . ?
C22 C23 C26 122.8(5) . . ?
C25 C24 C23 119.6(4) . . ?
N1 C25 C24 124.6(4) . . ?
C26 C26 C23 120.9(7) 2_856 . ?

_diffrn_measured_fraction_theta_max 0.996
_diffrn_reflns_theta_full        67.25
_diffrn_measured_fraction_theta_full 0.996
_refine_diff_density_max         0.487
_refine_diff_density_min         -0.321
_refine_diff_density_rms         0.064
####################################################################### 
# 
# 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_6b
_database_code_depnum_ccdc_archive 'CCDC 1053485'
_audit_update_record             
;
2015-03-12 deposited with the CCDC.
2015-05-13 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C13 H8.50 Cu0.50 N0.50 O3'
_chemical_formula_weight         251.47

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 '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 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cu Cu -1.9646 0.5888 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_H-M   C2/m

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

_cell_length_a                   14.434(2)
_cell_length_b                   19.805(4)
_cell_length_c                   10.6271(13)
_cell_angle_alpha                90.00
_cell_angle_beta                 130.336(9)
_cell_angle_gamma                90.00
_cell_volume                     2315.7(6)
_cell_formula_units_Z            8
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    422
_cell_measurement_theta_min      4.4790
_cell_measurement_theta_max      48.6250

_exptl_crystal_description       block
_exptl_crystal_colour            blue
_exptl_crystal_size_max          0.13
_exptl_crystal_size_mid          0.12
_exptl_crystal_size_min          0.12
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.443
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1028
_exptl_absorpt_coefficient_mu    1.695
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.8097
_exptl_absorpt_correction_T_max  0.8224
_exptl_absorpt_process_details   sadabs

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      293(2)
_diffrn_radiation_wavelength     1.54184
_diffrn_radiation_type           CuK\a
_diffrn_radiation_source         'Enhance (Cu) X-ray Source'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Xcalibur, Eos, Gemini'
_diffrn_measurement_method       ?
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            3631
_diffrn_reflns_av_R_equivalents  0.0666
_diffrn_reflns_av_sigmaI/netI    0.1257
_diffrn_reflns_limit_h_min       -17
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_k_max       23
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_theta_min         4.47
_diffrn_reflns_theta_max         67.25
_reflns_number_total             2119
_reflns_number_gt                1079
_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)+(0.1013P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         2119
_refine_ls_number_parameters     166
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1532
_refine_ls_R_factor_gt           0.0844
_refine_ls_wR_factor_ref         0.2529
_refine_ls_wR_factor_gt          0.1984
_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
Cu1 Cu 0.55524(12) 0.0000 0.65895(15) 0.0535(6) Uani 1 2 d S . .
O1 O 0.6516(4) 0.0693(3) 0.6544(6) 0.0642(15) Uani 1 1 d . . .
O2 O 0.5598(4) 0.0681(3) 0.3839(5) 0.0577(14) Uani 1 1 d . . .
O3 O 1.0308(5) 0.2407(4) 0.6825(6) 0.088(2) Uani 1 1 d . . .
N1 N 0.6793(7) 0.0000 0.9264(10) 0.053(2) Uani 1 2 d S . .
C1 C 0.6434(6) 0.0867(4) 0.5328(8) 0.057(2) Uani 1 1 d . . .
C2 C 0.7424(6) 0.1299(4) 0.5721(9) 0.057(2) Uani 1 1 d . . .
C3 C 0.8384(7) 0.1469(5) 0.7343(9) 0.078(3) Uani 1 1 d . . .
H3 H 0.8375 0.1336 0.8174 0.094 Uiso 1 1 calc R . .
C4 C 0.9370(7) 0.1840(5) 0.7745(9) 0.082(3) Uani 1 1 d . . .
H4 H 1.0008 0.1957 0.8837 0.099 Uiso 1 1 calc R . .
C5 C 0.9391(6) 0.2032(5) 0.6519(9) 0.065(2) Uani 1 1 d . . .
C6 C 0.8431(6) 0.1876(5) 0.4895(8) 0.064(2) Uani 1 1 d . . .
H6 H 0.8442 0.2014 0.4069 0.076 Uiso 1 1 calc R . .
C7 C 0.7458(6) 0.1517(4) 0.4493(8) 0.062(2) Uani 1 1 d . . .
H7 H 0.6812 0.1417 0.3392 0.075 Uiso 1 1 calc R . .
C8 C 1.1411(7) 0.2452(6) 0.8458(10) 0.069(2) Uani 1 1 d . . .
C9 C 1.1735(8) 0.3059(6) 0.9182(11) 0.084(3) Uani 1 1 d . . .
H9 H 1.1234 0.3433 0.8637 0.100 Uiso 1 1 calc R . .
C10 C 1.2138(9) 0.1885(6) 0.9203(12) 0.088(3) Uani 1 1 d . . .
H10 H 1.1889 0.1474 0.8648 0.105 Uiso 1 1 calc R . .
C11 C 0.6506(9) 0.0000 1.0205(12) 0.067(3) Uani 1 2 d S . .
H11 H 0.5683 0.0000 0.9678 0.080 Uiso 1 2 calc SR . .
C12 C 0.7318(13) 0.0000 1.1920(14) 0.097(5) Uani 1 2 d S . .
H12 H 0.7038 0.0000 1.2500 0.116 Uiso 1 2 calc SR . .
C13 C 0.8520(12) 0.0000 1.2727(14) 0.086(4) Uani 1 2 d S . .
C14 C 0.8876(10) 0.0000 1.1767(13) 0.086(4) Uani 1 2 d S . .
H14 H 0.9695 0.0000 1.2274 0.103 Uiso 1 2 calc SR . .
C15 C 0.7984(9) 0.0000 1.0042(12) 0.072(4) Uani 1 2 d S . .
H15 H 0.8226 0.0000 0.9416 0.086 Uiso 1 2 calc SR . .
C16 C 0.9429(11) 0.0000 1.4600(15) 0.140(7) Uani 1 2 d S . .
H16 H 0.9147 0.0000 1.5178 0.168 Uiso 1 2 calc SR . .


_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 1.950(5) 5_656 ?
Cu1 O2 1.950(5) 2_656 ?
Cu1 O1 1.977(5) . ?
Cu1 O1 1.977(5) 6 ?
Cu1 N1 2.167(8) . ?
Cu1 Cu1 2.642(3) 5_656 ?
O1 C1 1.267(8) . ?
O2 C1 1.274(8) . ?
O2 Cu1 1.950(5) 5_656 ?
O3 C5 1.359(9) . ?
O3 C8 1.406(9) . ?
N1 C11 1.306(13) . ?
N1 C15 1.342(12) . ?
C1 C2 1.476(10) . ?
C2 C3 1.384(10) . ?
C2 C7 1.405(10) . ?
C3 C4 1.400(10) . ?
C3 H3 0.9300 . ?
C4 C5 1.377(10) . ?
C4 H4 0.9300 . ?
C5 C6 1.378(9) . ?
C6 C7 1.371(9) . ?
C6 H6 0.9300 . ?
C7 H7 0.9300 . ?
C8 C9 1.339(13) . ?
C8 C10 1.383(12) . ?
C9 C10 1.410(11) 7_757 ?
C9 H9 0.9300 . ?
C10 C9 1.410(11) 7_757 ?
C10 H10 0.9300 . ?
C11 C12 1.389(14) . ?
C11 H11 0.9300 . ?
C12 C13 1.348(17) . ?
C12 H12 0.9300 . ?
C13 C14 1.408(16) . ?
C13 C16 1.517(15) . ?
C14 C15 1.401(13) . ?
C14 H14 0.9300 . ?
C15 H15 0.9300 . ?
C16 C16 1.28(3) 5_758 ?
C16 H16 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 O2 87.4(3) 5_656 2_656 ?
O2 Cu1 O1 168.66(19) 5_656 . ?
O2 Cu1 O1 91.2(2) 2_656 . ?
O2 Cu1 O1 91.2(2) 5_656 6 ?
O2 Cu1 O1 168.66(19) 2_656 6 ?
O1 Cu1 O1 87.9(3) . 6 ?
O2 Cu1 N1 99.3(2) 5_656 . ?
O2 Cu1 N1 99.3(2) 2_656 . ?
O1 Cu1 N1 92.0(2) . . ?
O1 Cu1 N1 92.0(2) 6 . ?
O2 Cu1 Cu1 89.04(13) 5_656 5_656 ?
O2 Cu1 Cu1 89.04(13) 2_656 5_656 ?
O1 Cu1 Cu1 79.67(15) . 5_656 ?
O1 Cu1 Cu1 79.67(15) 6 5_656 ?
N1 Cu1 Cu1 168.4(2) . 5_656 ?
C1 O1 Cu1 127.7(5) . . ?
C1 O2 Cu1 118.0(5) . 5_656 ?
C5 O3 C8 118.6(6) . . ?
C11 N1 C15 116.3(9) . . ?
C11 N1 Cu1 127.0(7) . . ?
C15 N1 Cu1 116.7(7) . . ?
O1 C1 O2 125.2(7) . . ?
O1 C1 C2 115.8(6) . . ?
O2 C1 C2 119.0(6) . . ?
C3 C2 C7 118.3(7) . . ?
C3 C2 C1 119.9(7) . . ?
C7 C2 C1 121.7(6) . . ?
C2 C3 C4 120.5(7) . . ?
C2 C3 H3 119.7 . . ?
C4 C3 H3 119.7 . . ?
C5 C4 C3 119.8(7) . . ?
C5 C4 H4 120.1 . . ?
C3 C4 H4 120.1 . . ?
O3 C5 C4 122.6(6) . . ?
O3 C5 C6 117.2(7) . . ?
C4 C5 C6 120.1(7) . . ?
C7 C6 C5 120.3(7) . . ?
C7 C6 H6 119.9 . . ?
C5 C6 H6 119.9 . . ?
C6 C7 C2 120.9(6) . . ?
C6 C7 H7 119.6 . . ?
C2 C7 H7 119.6 . . ?
C9 C8 C10 123.1(8) . . ?
C9 C8 O3 117.5(9) . . ?
C10 C8 O3 119.2(9) . . ?
C8 C9 C10 118.0(10) . 7_757 ?
C8 C9 H9 121.0 . . ?
C10 C9 H9 121.0 7_757 . ?
C8 C10 C9 118.9(9) . 7_757 ?
C8 C10 H10 120.6 . . ?
C9 C10 H10 120.6 7_757 . ?
N1 C11 C12 126.0(11) . . ?
N1 C11 H11 117.0 . . ?
C12 C11 H11 117.0 . . ?
C13 C12 C11 118.7(12) . . ?
C13 C12 H12 120.7 . . ?
C11 C12 H12 120.7 . . ?
C12 C13 C14 117.5(10) . . ?
C12 C13 C16 119.9(12) . . ?
C14 C13 C16 122.6(12) . . ?
C15 C14 C13 119.4(11) . . ?
C15 C14 H14 120.3 . . ?
C13 C14 H14 120.3 . . ?
N1 C15 C14 122.1(11) . . ?
N1 C15 H15 118.9 . . ?
C14 C15 H15 118.9 . . ?
C16 C16 C13 121.4(18) 5_758 . ?
C16 C16 H16 119.3 5_758 . ?
C13 C16 H16 119.3 . . ?

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 C1 -11.3(15) 5_656 . . . ?
O2 Cu1 O1 C1 -94.2(7) 2_656 . . . ?
O1 Cu1 O1 C1 74.5(7) 6 . . . ?
N1 Cu1 O1 C1 166.4(6) . . . . ?
Cu1 Cu1 O1 C1 -5.4(6) 5_656 . . . ?
O2 Cu1 N1 C11 -44.46(16) 5_656 . . . ?
O2 Cu1 N1 C11 44.46(16) 2_656 . . . ?
O1 Cu1 N1 C11 136.00(17) . . . . ?
O1 Cu1 N1 C11 -136.00(17) 6 . . . ?
Cu1 Cu1 N1 C11 180.000(8) 5_656 . . . ?
O2 Cu1 N1 C15 135.54(16) 5_656 . . . ?
O2 Cu1 N1 C15 -135.54(16) 2_656 . . . ?
O1 Cu1 N1 C15 -44.00(17) . . . . ?
O1 Cu1 N1 C15 44.00(17) 6 . . . ?
Cu1 Cu1 N1 C15 0.000(7) 5_656 . . . ?
Cu1 O1 C1 O2 9.4(12) . . . . ?
Cu1 O1 C1 C2 -168.3(5) . . . . ?
Cu1 O2 C1 O1 -7.0(11) 5_656 . . . ?
Cu1 O2 C1 C2 170.6(5) 5_656 . . . ?
O1 C1 C2 C3 2.3(12) . . . . ?
O2 C1 C2 C3 -175.6(8) . . . . ?
O1 C1 C2 C7 178.8(7) . . . . ?
O2 C1 C2 C7 0.9(12) . . . . ?
C7 C2 C3 C4 -1.0(14) . . . . ?
C1 C2 C3 C4 175.6(8) . . . . ?
C2 C3 C4 C5 -0.7(15) . . . . ?
C8 O3 C5 C4 17.0(14) . . . . ?
C8 O3 C5 C6 -166.3(8) . . . . ?
C3 C4 C5 O3 178.4(8) . . . . ?
C3 C4 C5 C6 1.8(15) . . . . ?
O3 C5 C6 C7 -178.0(8) . . . . ?
C4 C5 C6 C7 -1.2(14) . . . . ?
C5 C6 C7 C2 -0.5(13) . . . . ?
C3 C2 C7 C6 1.6(13) . . . . ?
C1 C2 C7 C6 -175.0(8) . . . . ?
C5 O3 C8 C9 -115.1(10) . . . . ?
C5 O3 C8 C10 68.6(11) . . . . ?
C10 C8 C9 C10 -1.5(16) . . . 7_757 ?
O3 C8 C9 C10 -177.6(7) . . . 7_757 ?
C9 C8 C10 C9 1.6(17) . . . 7_757 ?
O3 C8 C10 C9 177.6(7) . . . 7_757 ?
C15 N1 C11 C12 0.000(10) . . . . ?
Cu1 N1 C11 C12 180.000(5) . . . . ?
N1 C11 C12 C13 0.000(7) . . . . ?
C11 C12 C13 C14 0.000(10) . . . . ?
C11 C12 C13 C16 180.000(9) . . . . ?
C12 C13 C14 C15 0.000(10) . . . . ?
C16 C13 C14 C15 180.000(10) . . . . ?
C11 N1 C15 C14 0.000(5) . . . . ?
Cu1 N1 C15 C14 180.000(7) . . . . ?
C13 C14 C15 N1 0.000(6) . . . . ?
C12 C13 C16 C16 180.000(14) . . . 5_758 ?
C14 C13 C16 C16 0.000(4) . . . 5_758 ?

_diffrn_measured_fraction_theta_max 0.986
_diffrn_reflns_theta_full        67.25
_diffrn_measured_fraction_theta_full 0.986
_refine_diff_density_max         0.735
_refine_diff_density_min         -0.480
_refine_diff_density_rms         0.088
####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_4
_database_code_depnum_ccdc_archive 'CCDC 1053489'
_audit_update_record             
;
2015-03-12 deposited with the CCDC.
2015-05-13 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C32 H22 Mn N2 O7'
_chemical_formula_weight         601.46

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'
Mn Mn 0.3368 0.7283 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_H-M   P21

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

_cell_length_a                   6.3847(12)
_cell_length_b                   21.746(4)
_cell_length_c                   10.1336(19)
_cell_angle_alpha                90.00
_cell_angle_beta                 105.085(4)
_cell_angle_gamma                90.00
_cell_volume                     1358.5(4)
_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            ?
_exptl_crystal_size_max          ?
_exptl_crystal_size_mid          ?
_exptl_crystal_size_min          ?
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.470
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             618
_exptl_absorpt_coefficient_mu    0.540
_exptl_absorpt_correction_type   ?
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   ?

_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  ?
_diffrn_measurement_method       ?
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            7646
_diffrn_reflns_av_R_equivalents  0.0353
_diffrn_reflns_av_sigmaI/netI    0.0509
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_k_max       25
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_theta_min         1.87
_diffrn_reflns_theta_max         25.02
_reflns_number_total             4798
_reflns_number_gt                3075
_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)+(0.0940P)²+0.0231P] 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   0.32(3)
_refine_ls_number_reflns         4798
_refine_ls_number_parameters     384
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0594
_refine_ls_R_factor_gt           0.0509
_refine_ls_wR_factor_ref         0.1445
_refine_ls_wR_factor_gt          0.1385
_refine_ls_goodness_of_fit_ref   1.086
_refine_ls_restrained_S_all      1.085
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
Mn1 Mn 0.50289(11) 0.19777(4) 0.78975(6) 0.0420(2) Uani 1 1 d . . .
C20 C 0.8931(8) 0.0644(3) 1.0071(5) 0.0397(11) Uani 1 1 d . . .
O32 O 0.5648(7) 0.1087(2) 0.8789(4) 0.0585(11) Uani 1 1 d . . .
C19 C 0.7680(8) 0.1109(3) 0.9086(5) 0.0405(11) Uani 1 1 d . . .
C29 C 0.7029(9) 0.3639(3) 1.0412(5) 0.0413(12) Uani 1 1 d . . .
O33 O 0.8608(6) 0.1516(2) 0.8595(4) 0.0605(11) Uani 1 1 d . . .
C10 C 0.2906(8) 0.1927(3) 0.4738(4) 0.0453(12) Uani 1 1 d . . .
N1 N 0.2560(7) 0.1688(2) 0.5906(4) 0.0469(11) Uani 1 1 d . . .
C32 C 0.9514(10) 0.4489(3) 1.2155(5) 0.0543(15) Uani 1 1 d . . .
C25 C 1.1181(9) 0.0660(3) 1.0499(5) 0.0484(13) Uani 1 1 d . . .
H15 H 1.1951 0.0950 1.0140 0.058 Uiso 1 1 calc R . .
C15 C 0.4782(10) 0.2315(3) 0.4878(5) 0.0509(14) Uani 1 1 d . . .
C33 C 0.7299(10) 0.4562(3) 1.1742(6) 0.0591(16) Uani 1 1 d . . .
H23 H 0.6624 0.4892 1.2044 0.071 Uiso 1 1 calc R . .
C30 C 0.9228(10) 0.3576(3) 1.0813(6) 0.0570(15) Uani 1 1 d . . .
H26 H 0.9884 0.3250 1.0481 0.068 Uiso 1 1 calc R . .
O34 O 0.6543(7) 0.2708(2) 0.9159(5) 0.0676(13) Uani 1 1 d . . .
O36 O 0.2328(7) 0.2136(2) 0.8734(5) 0.0692(14) Uani 1 1 d . . .
H36 H 0.1645 0.1815 0.8715 0.104 Uiso 1 1 calc R . .
C24 C 1.2269(9) 0.0240(3) 1.1467(6) 0.0546(14) Uani 1 1 d . . .
H16 H 1.3772 0.0254 1.1787 0.066 Uiso 1 1 calc R . .
N2 N 0.6065(7) 0.2417(2) 0.6163(4) 0.0470(11) Uani 1 1 d . . .
C34 C 0.6113(9) 0.4128(3) 1.0864(6) 0.0518(14) Uani 1 1 d . . .
H22 H 0.4616 0.4175 1.0571 0.062 Uiso 1 1 calc R . .
C21 C 0.7818(9) 0.0203(3) 1.0568(6) 0.0528(15) Uani 1 1 d . . .
H19 H 0.6312 0.0191 1.0267 0.063 Uiso 1 1 calc R . .
C22 C 0.8905(11) -0.0234(3) 1.1523(7) 0.0666(18) Uani 1 1 d . . .
H18 H 0.8146 -0.0537 1.1852 0.080 Uiso 1 1 calc R . .
C23 C 1.1096(10) -0.0199(3) 1.1949(6) 0.0527(15) Uani 1 1 d . . .
C28 C 0.5604(9) 0.3174(3) 0.9476(6) 0.0483(13) Uani 1 1 d . . .
C9 C -0.0305(13) 0.1459(4) 0.3381(7) 0.0730(19) Uani 1 1 d . . .
H3 H -0.1282 0.1382 0.2541 0.088 Uiso 1 1 calc R . .
C11 C 0.1513(11) 0.1819(3) 0.3447(5) 0.0621(17) Uani 1 1 d . . .
C31 C 1.0509(10) 0.3997(4) 1.1718(8) 0.0646(18) Uani 1 1 d . . .
H25 H 1.2004 0.3945 1.2017 0.077 Uiso 1 1 calc R . .
C7 C 0.0819(10) 0.1348(3) 0.5803(6) 0.0570(15) Uani 1 1 d . . .
H7 H 0.0553 0.1186 0.6593 0.068 Uiso 1 1 calc R . .
C17 C 0.8397(15) 0.3013(5) 0.5175(11) 0.098(3) Uani 1 1 d . . .
H17 H 0.9648 0.3249 0.5302 0.118 Uiso 1 1 calc R . .
C8 C -0.0659(12) 0.1221(4) 0.4530(7) 0.0735(19) Uani 1 1 d . . .
H2 H -0.1867 0.0975 0.4486 0.088 Uiso 1 1 calc R . .
C14 C 0.5263(13) 0.2560(4) 0.3695(7) 0.074(2) Uani 1 1 d . . .
C13 C 0.3789(17) 0.2441(5) 0.2405(6) 0.095(3) Uani 1 1 d . . .
H8 H 0.4058 0.2610 0.1623 0.114 Uiso 1 1 calc R . .
C12 C 0.2010(16) 0.2088(5) 0.2285(6) 0.091(3) Uani 1 1 d . . .
H9 H 0.1087 0.2019 0.1423 0.109 Uiso 1 1 calc R . .
C18 C 0.7831(10) 0.2762(4) 0.6299(7) 0.0701(19) Uani 1 1 d . . .
H12 H 0.8712 0.2839 0.7170 0.084 Uiso 1 1 calc R . .
C16 C 0.7133(17) 0.2914(5) 0.3905(9) 0.098(3) Uani 1 1 d . . .
H10 H 0.7515 0.3085 0.3159 0.117 Uiso 1 1 calc R . .
O38 O 1.0680(8) 0.4945(2) 1.2972(5) 0.0810(16) Uani 1 1 d . . .
O35 O 0.3622(8) 0.3265(2) 0.9119(6) 0.0878(17) Uani 1 1 d . . .
C35 C 1.2505(11) 0.4775(3) 1.4015(6) 0.0578(16) Uani 1 1 d . . .
C26 C 1.3957(10) -0.0484(3) 1.3892(5) 0.0527(14) Uani 1 1 d . . .
O37 O 1.2105(9) -0.0660(2) 1.2865(5) 0.0799(15) Uani 1 1 d . . .
C36 C 1.4332(11) 0.5120(3) 1.4175(6) 0.0609(16) Uani 1 1 d . . .
H36A H 1.4370 0.5442 1.3578 0.073 Uiso 1 1 calc R . .
C27 C 1.3847(11) -0.0014(4) 1.4752(7) 0.0696(18) Uani 1 1 d . . .
H27 H 1.2581 0.0215 1.4632 0.084 Uiso 1 1 calc R . .
C6 C 1.5757(13) -0.0824(4) 1.4038(7) 0.075(2) Uani 1 1 d . . .
H6 H 1.5791 -0.1145 1.3437 0.089 Uiso 1 1 calc R . .
C37 C 1.2414(12) 0.4310(4) 1.4890(8) 0.081(2) Uani 1 1 d . . .
H37 H 1.1148 0.4082 1.4781 0.097 Uiso 1 1 calc R . .
H1 H 0.096(14) 0.211(5) 0.880(9) 0.11(3) Uiso 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
Mn1 O34 2.109(4) . ?
Mn1 O32 2.130(4) . ?
Mn1 O36 2.138(4) . ?
Mn1 N2 2.246(4) . ?
Mn1 N1 2.302(4) . ?
Mn1 O33 2.426(4) . ?
C20 C21 1.365(8) . ?
C20 C25 1.389(7) . ?
C20 C19 1.499(7) . ?
O32 C19 1.254(6) . ?
C19 O33 1.239(7) . ?
C29 C34 1.350(8) . ?
C29 C30 1.363(8) . ?
C29 C28 1.517(8) . ?
C10 N1 1.362(6) . ?
C10 C11 1.397(7) . ?
C10 C15 1.442(8) . ?
N1 C7 1.315(8) . ?
C32 C33 1.375(9) . ?
C32 C31 1.375(10) . ?
C32 O38 1.379(8) . ?
C25 C24 1.388(8) . ?
C15 N2 1.363(7) . ?
C15 C14 1.417(8) . ?
C33 C34 1.379(9) . ?
C30 C31 1.400(9) . ?
O34 C28 1.261(8) . ?
C24 C23 1.377(9) . ?
N2 C18 1.332(8) . ?
C21 C22 1.403(9) . ?
C22 C23 1.355(9) . ?
C23 O37 1.405(7) . ?
C28 O35 1.239(7) . ?
C9 C8 1.346(11) . ?
C9 C11 1.387(11) . ?
C11 C12 1.422(10) . ?
C7 C8 1.414(9) . ?
C17 C16 1.347(12) . ?
C17 C18 1.392(11) . ?
C14 C16 1.390(12) . ?
C14 C13 1.422(12) . ?
C13 C12 1.350(12) . ?
O38 C35 1.404(7) . ?
C35 C37 1.355(10) . ?
C35 C36 1.361(9) . ?
C26 C6 1.342(9) . ?
C26 C27 1.356(10) . ?
C26 O37 1.409(7) . ?
C36 C27 1.400(9) 2_858 ?
C27 C36 1.400(9) 2_848 ?
C6 C37 1.403(10) 2_848 ?
C37 C6 1.403(10) 2_858 ?

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
O34 Mn1 O32 114.98(19) . . ?
O34 Mn1 O36 85.89(18) . . ?
O32 Mn1 O36 93.3(2) . . ?
O34 Mn1 N2 88.44(18) . . ?
O32 Mn1 N2 131.17(18) . . ?
O36 Mn1 N2 132.40(19) . . ?
O34 Mn1 N1 147.0(2) . . ?
O32 Mn1 N1 97.57(17) . . ?
O36 Mn1 N1 87.28(17) . . ?
N2 Mn1 N1 72.80(15) . . ?
O34 Mn1 O33 83.48(18) . . ?
O32 Mn1 O33 56.21(15) . . ?
O36 Mn1 O33 138.30(17) . . ?
N2 Mn1 O33 87.52(15) . . ?
N1 Mn1 O33 121.34(17) . . ?
C21 C20 C25 119.9(5) . . ?
C21 C20 C19 118.8(5) . . ?
C25 C20 C19 121.3(5) . . ?
C19 O32 Mn1 97.6(3) . . ?
O33 C19 O32 120.3(5) . . ?
O33 C19 C20 121.5(5) . . ?
O32 C19 C20 118.2(5) . . ?
C34 C29 C30 118.8(5) . . ?
C34 C29 C28 119.7(5) . . ?
C30 C29 C28 121.5(5) . . ?
C19 O33 Mn1 84.2(3) . . ?
N1 C10 C11 122.8(5) . . ?
N1 C10 C15 117.2(4) . . ?
C11 C10 C15 120.0(5) . . ?
C7 N1 C10 118.1(5) . . ?
C7 N1 Mn1 126.5(4) . . ?
C10 N1 Mn1 115.3(4) . . ?
C33 C32 C31 121.1(6) . . ?
C33 C32 O38 116.8(6) . . ?
C31 C32 O38 122.0(6) . . ?
C24 C25 C20 119.4(5) . . ?
N2 C15 C14 122.5(6) . . ?
N2 C15 C10 117.8(4) . . ?
C14 C15 C10 119.6(5) . . ?
C32 C33 C34 117.8(6) . . ?
C29 C30 C31 120.6(6) . . ?
C28 O34 Mn1 125.9(4) . . ?
C23 C24 C25 119.2(5) . . ?
C18 N2 C15 118.2(5) . . ?
C18 N2 Mn1 124.9(4) . . ?
C15 N2 Mn1 116.9(4) . . ?
C29 C34 C33 122.9(5) . . ?
C20 C21 C22 121.2(5) . . ?
C23 C22 C21 117.8(6) . . ?
C22 C23 C24 122.5(5) . . ?
C22 C23 O37 115.3(6) . . ?
C24 C23 O37 122.1(5) . . ?
O35 C28 O34 124.9(6) . . ?
O35 C28 C29 118.5(6) . . ?
O34 C28 C29 116.6(5) . . ?
C8 C9 C11 120.1(6) . . ?
C9 C11 C10 117.5(6) . . ?
C9 C11 C12 123.8(6) . . ?
C10 C11 C12 118.8(6) . . ?
C32 C31 C30 118.7(6) . . ?
N1 C7 C8 122.1(6) . . ?
C16 C17 C18 120.0(8) . . ?
C9 C8 C7 119.5(7) . . ?
C16 C14 C15 116.5(7) . . ?
C16 C14 C13 125.3(7) . . ?
C15 C14 C13 118.2(7) . . ?
C12 C13 C14 121.8(6) . . ?
C13 C12 C11 121.5(6) . . ?
N2 C18 C17 122.0(7) . . ?
C17 C16 C14 120.8(7) . . ?
C32 O38 C35 118.4(5) . . ?
C37 C35 C36 121.0(6) . . ?
C37 C35 O38 121.4(6) . . ?
C36 C35 O38 117.5(6) . . ?
C6 C26 C27 122.0(6) . . ?
C6 C26 O37 117.5(6) . . ?
C27 C26 O37 120.4(6) . . ?
C26 O37 C23 116.5(5) . . ?
C35 C36 C27 119.4(7) . 2_858 ?
C26 C27 C36 119.0(6) . 2_848 ?
C26 C6 C37 119.1(6) . 2_848 ?
C35 C37 C6 119.5(6) . 2_858 ?

_diffrn_measured_fraction_theta_max 0.998
_diffrn_reflns_theta_full        25.02
_diffrn_measured_fraction_theta_full 0.998
_refine_diff_density_max         0.415
_refine_diff_density_min         -0.419
_refine_diff_density_rms         0.062
####################################################################### 
# 
# 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_5
_database_code_depnum_ccdc_archive 'CCDC 1053492'
_audit_update_record             
;
2015-03-12 deposited with the CCDC.
2015-05-13 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C16 H11 N Ni0.50 O3.50'
_chemical_formula_weight         302.61

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 '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 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Ni Ni -3.0029 0.5091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_H-M   Pccn

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

_cell_length_a                   5.83670(16)
_cell_length_b                   22.1190(6)
_cell_length_c                   20.4593(5)
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_volume                     2641.33(12)
_cell_formula_units_Z            8
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    4864
_cell_measurement_theta_min      4.5460
_cell_measurement_theta_max      71.2240

_exptl_crystal_description       strip
_exptl_crystal_colour            ?
_exptl_crystal_size_max          0.13
_exptl_crystal_size_mid          0.12
_exptl_crystal_size_min          0.11
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.522
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1248
_exptl_absorpt_coefficient_mu    1.533
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.8256
_exptl_absorpt_correction_T_max  0.8495
_exptl_absorpt_process_details   sadabs

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      293(2)
_diffrn_radiation_wavelength     1.54184
_diffrn_radiation_type           CuK\a
_diffrn_radiation_source         'Enhance (Cu) X-ray Source'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Xcalibur, Eos, Gemini'
_diffrn_measurement_method       ?
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            14373
_diffrn_reflns_av_R_equivalents  0.0329
_diffrn_reflns_av_sigmaI/netI    0.0199
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_h_max       5
_diffrn_reflns_limit_k_min       -26
_diffrn_reflns_limit_k_max       25
_diffrn_reflns_limit_l_min       -24
_diffrn_reflns_limit_l_max       24
_diffrn_reflns_theta_min         4.00
_diffrn_reflns_theta_max         67.24
_reflns_number_total             2366
_reflns_number_gt                2031
_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)+(0.0686P)²+0.7564P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         2366
_refine_ls_number_parameters     191
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0444
_refine_ls_R_factor_gt           0.0386
_refine_ls_wR_factor_ref         0.1115
_refine_ls_wR_factor_gt          0.1057
_refine_ls_goodness_of_fit_ref   1.032
_refine_ls_restrained_S_all      1.032
_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
Ni1 Ni 0.7500 0.7500 0.38126(2) 0.04085(18) Uani 1 2 d S . .
N1 N 0.9354(3) 0.71475(7) 0.45680(8) 0.0426(4) Uani 1 1 d . . .
O1 O 0.9076(3) 0.69903(7) 0.31079(7) 0.0599(5) Uani 1 1 d . . .
O2 O 0.5885(2) 0.66589(6) 0.35307(6) 0.0452(4) Uani 1 1 d . . .
O3 O 0.6962(3) 0.49360(8) 0.10369(8) 0.0585(4) Uani 1 1 d . . .
O4 O 0.7500 0.2500 0.26615(12) 0.0836(9) Uani 1 2 d S . .
H4C H 0.6471 0.2653 0.2419 0.100 Uiso 0.50 1 d PR . .
H4D H 0.8529 0.2347 0.2419 0.100 Uiso 0.50 1 d PR . .
C1 C 0.7433(3) 0.66178(9) 0.31061(9) 0.0427(5) Uani 1 1 d . . .
C2 C 0.7354(3) 0.61502(9) 0.25791(9) 0.0392(4) Uani 1 1 d . . .
C3 C 0.9148(3) 0.61139(9) 0.21343(9) 0.0448(5) Uani 1 1 d . . .
H3 H 1.0421 0.6362 0.2187 0.054 Uiso 1 1 calc R . .
C4 C 0.9067(4) 0.57153(9) 0.16159(10) 0.0453(5) Uani 1 1 d . . .
H4 H 1.0276 0.5695 0.1321 0.054 Uiso 1 1 calc R . .
C5 C 0.7180(3) 0.53476(9) 0.15395(10) 0.0415(4) Uani 1 1 d . . .
C6 C 0.5395(4) 0.53693(9) 0.19845(10) 0.0454(5) Uani 1 1 d . . .
H6 H 0.4143 0.5113 0.1937 0.054 Uiso 1 1 calc R . .
C7 C 0.5479(3) 0.57729(9) 0.24988(9) 0.0425(5) Uani 1 1 d . . .
H7 H 0.4268 0.5792 0.2794 0.051 Uiso 1 1 calc R . .
C8 C 0.8531(4) 0.49771(9) 0.05190(10) 0.0462(5) Uani 1 1 d . . .
C9 C 0.8000(4) 0.53333(11) -0.00123(12) 0.0546(5) Uani 1 1 d . . .
H9 H 0.6649 0.5556 -0.0019 0.065 Uiso 1 1 calc R . .
C10 C 1.0504(4) 0.46442(11) 0.05367(10) 0.0553(6) Uani 1 1 d . . .
H10 H 1.0837 0.4405 0.0898 0.066 Uiso 1 1 calc R . .
C11 C 1.1205(4) 0.67973(11) 0.45599(14) 0.0614(6) Uani 1 1 d . . .
H11 H 1.1831 0.6685 0.4160 0.074 Uiso 1 1 calc R . .
C12 C 1.2237(5) 0.65938(13) 0.5136(2) 0.0814(10) Uani 1 1 d . . .
H12 H 1.3530 0.6349 0.5114 0.098 Uiso 1 1 calc R . .
C13 C 1.1364(6) 0.67509(13) 0.57229(17) 0.0806(9) Uani 1 1 d . . .
H13 H 1.2054 0.6615 0.6106 0.097 Uiso 1 1 calc R . .
C14 C 0.9419(4) 0.71185(10) 0.57525(11) 0.0583(6) Uani 1 1 d . . .
C15 C 0.8481(3) 0.73066(9) 0.51554(9) 0.0403(4) Uani 1 1 d . . .
C16 C 0.8403(6) 0.73203(15) 0.63475(11) 0.0816(10) Uani 1 1 d . . .
H16 H 0.9025 0.7196 0.6744 0.098 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
Ni1 N1 2.0415(16) 2_665 ?
Ni1 N1 2.0415(16) . ?
Ni1 O1 2.0483(15) . ?
Ni1 O1 2.0483(15) 2_665 ?
Ni1 O2 2.1638(13) . ?
Ni1 O2 2.1638(13) 2_665 ?
Ni1 C1 2.429(2) . ?
Ni1 C1 2.429(2) 2_665 ?
N1 C11 1.329(3) . ?
N1 C15 1.352(2) . ?
O1 C1 1.265(2) . ?
O2 C1 1.256(2) . ?
O3 C5 1.379(2) . ?
O3 C8 1.403(3) . ?
C1 C2 1.495(3) . ?
C2 C7 1.386(3) . ?
C2 C3 1.390(3) . ?
C3 C4 1.380(3) . ?
C4 C5 1.378(3) . ?
C5 C6 1.385(3) . ?
C6 C7 1.381(3) . ?
C8 C10 1.367(3) . ?
C8 C9 1.378(3) . ?
C9 C10 1.384(3) 5_765 ?
C10 C9 1.384(3) 5_765 ?
C11 C12 1.397(4) . ?
C12 C13 1.350(5) . ?
C13 C14 1.398(4) . ?
C14 C15 1.402(3) . ?
C14 C16 1.426(4) . ?
C15 C15 1.430(4) 2_665 ?
C16 C16 1.320(7) 2_665 ?

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 Ni1 N1 81.59(9) 2_665 . ?
N1 Ni1 O1 168.85(6) 2_665 . ?
N1 Ni1 O1 94.85(7) . . ?
N1 Ni1 O1 94.85(7) 2_665 2_665 ?
N1 Ni1 O1 168.85(6) . 2_665 ?
O1 Ni1 O1 90.53(11) . 2_665 ?
N1 Ni1 O2 107.41(6) 2_665 . ?
N1 Ni1 O2 95.98(6) . . ?
O1 Ni1 O2 62.28(5) . . ?
O1 Ni1 O2 95.17(6) 2_665 . ?
N1 Ni1 O2 95.98(6) 2_665 2_665 ?
N1 Ni1 O2 107.41(6) . 2_665 ?
O1 Ni1 O2 95.17(6) . 2_665 ?
O1 Ni1 O2 62.28(5) 2_665 2_665 ?
O2 Ni1 O2 149.09(7) . 2_665 ?
N1 Ni1 C1 138.49(7) 2_665 . ?
N1 Ni1 C1 98.76(7) . . ?
O1 Ni1 C1 31.37(6) . . ?
O1 Ni1 C1 90.92(7) 2_665 . ?
O2 Ni1 C1 31.08(6) . . ?
O2 Ni1 C1 122.63(6) 2_665 . ?
N1 Ni1 C1 98.76(7) 2_665 2_665 ?
N1 Ni1 C1 138.49(7) . 2_665 ?
O1 Ni1 C1 90.92(7) . 2_665 ?
O1 Ni1 C1 31.37(6) 2_665 2_665 ?
O2 Ni1 C1 122.63(6) . 2_665 ?
O2 Ni1 C1 31.08(6) 2_665 2_665 ?
C1 Ni1 C1 106.96(9) . 2_665 ?
C11 N1 C15 117.97(19) . . ?
C11 N1 Ni1 130.09(16) . . ?
C15 N1 Ni1 111.94(13) . . ?
C1 O1 Ni1 91.15(12) . . ?
C1 O2 Ni1 86.18(12) . . ?
C5 O3 C8 117.38(16) . . ?
O2 C1 O1 119.74(18) . . ?
O2 C1 C2 121.78(18) . . ?
O1 C1 C2 118.45(17) . . ?
O2 C1 Ni1 62.74(10) . . ?
O1 C1 Ni1 57.48(10) . . ?
C2 C1 Ni1 170.30(14) . . ?
C7 C2 C3 118.85(18) . . ?
C7 C2 C1 121.76(17) . . ?
C3 C2 C1 119.29(17) . . ?
C4 C3 C2 120.97(18) . . ?
C5 C4 C3 119.44(18) . . ?
C4 C5 O3 123.22(18) . . ?
C4 C5 C6 120.44(18) . . ?
O3 C5 C6 116.33(18) . . ?
C7 C6 C5 119.77(18) . . ?
C6 C7 C2 120.52(18) . . ?
C10 C8 C9 121.2(2) . . ?
C10 C8 O3 119.6(2) . . ?
C9 C8 O3 119.1(2) . . ?
C8 C9 C10 119.3(2) . 5_765 ?
C8 C10 C9 119.4(2) . 5_765 ?
N1 C11 C12 121.8(3) . . ?
C13 C12 C11 120.3(3) . . ?
C12 C13 C14 119.6(2) . . ?
C13 C14 C15 116.9(2) . . ?
C13 C14 C16 123.8(2) . . ?
C15 C14 C16 119.3(2) . . ?
N1 C15 C14 123.4(2) . . ?
N1 C15 C15 117.24(11) . 2_665 ?
C14 C15 C15 119.37(14) . 2_665 ?
C16 C16 C14 121.37(16) 2_665 . ?

_diffrn_measured_fraction_theta_max 1.000
_diffrn_reflns_theta_full        67.24
_diffrn_measured_fraction_theta_full 1.000
_refine_diff_density_max         0.212
_refine_diff_density_min         -0.404
_refine_diff_density_rms         0.050
####################################################################### 
# 
# 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_exp_3261
_database_code_depnum_ccdc_archive 'CCDC 1053493'
_audit_update_record             
;
2015-03-12 deposited with the CCDC.
2015-05-13 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C20 H0 O12 Zn'
_chemical_formula_weight         497.57

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Zn Zn 0.2839 1.4301 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_symmetry_cell_setting           ?
_symmetry_space_group_name_H-M   ?

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                   36.745(3)
_cell_length_b                   5.5792(8)
_cell_length_c                   8.6871(8)
_cell_angle_alpha                90.00
_cell_angle_beta                 92.931(8)
_cell_angle_gamma                90.00
_cell_volume                     1778.6(3)
_cell_formula_units_Z            4
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    ?
_cell_measurement_theta_min      ?
_cell_measurement_theta_max      ?

_exptl_crystal_description       ?
_exptl_crystal_colour            ?
_exptl_crystal_size_max          ?
_exptl_crystal_size_mid          ?
_exptl_crystal_size_min          ?
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.858
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             984
_exptl_absorpt_coefficient_mu    1.457
_exptl_absorpt_correction_type   ?
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   ?

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      293(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  ?
_diffrn_measurement_method       ?
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            6055
_diffrn_reflns_av_R_equivalents  0.0664
_diffrn_reflns_av_sigmaI/netI    0.1258
_diffrn_reflns_limit_h_min       -23
_diffrn_reflns_limit_h_max       43
_diffrn_reflns_limit_k_min       -6
_diffrn_reflns_limit_k_max       5
_diffrn_reflns_limit_l_min       -10
_diffrn_reflns_limit_l_max       10
_diffrn_reflns_theta_min         2.78
_diffrn_reflns_theta_max         25.01
_reflns_number_total             3145
_reflns_number_gt                2092
_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)+(0.1069P)²+43.2216P] 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         3145
_refine_ls_number_parameters     268
_refine_ls_number_restraints     10
_refine_ls_R_factor_all          0.1431
_refine_ls_R_factor_gt           0.1028
_refine_ls_wR_factor_ref         0.2944
_refine_ls_wR_factor_gt          0.2618
_refine_ls_goodness_of_fit_ref   0.956
_refine_ls_restrained_S_all      0.955
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
Zn1 Zn 0.74176(4) 0.1752(2) 0.67355(14) 0.0280(4) Uani 1 1 d D . .
O2 O 0.7722(2) 0.5785(18) 0.5637(9) 0.043(2) Uani 1 1 d . . .
O8 O 0.7292(2) 0.3992(16) 0.9533(8) 0.035(2) Uani 1 1 d . . .
O4 O 0.9336(2) 0.584(3) 0.3507(11) 0.072(4) Uani 1 1 d . . .
O6 O 0.5669(2) 0.604(2) 1.1399(10) 0.064(3) Uani 1 1 d . . .
C22 C 0.7000(3) 0.396(2) 0.8801(12) 0.027(2) Uani 1 1 d . . .
C23 C 0.5979(3) 0.552(2) 1.0674(12) 0.034(3) Uani 1 1 d . . .
C20 C 0.6646(3) 0.4544(18) 0.9474(11) 0.020(2) Uani 1 1 d . . .
C19 C 0.8339(3) 0.478(2) 0.5379(12) 0.027(2) Uani 1 1 d . . .
C1 C 0.6339(3) 0.323(2) 0.9005(12) 0.029(3) Uani 1 1 d . . .
H1 H 0.6358 0.2006 0.8283 0.035 Uiso 1 1 calc R . .
C2 C 0.7978(3) 0.433(2) 0.5954(12) 0.028(2) Uani 1 1 d . . .
C3 C 0.5336(3) 0.548(3) 1.0632(14) 0.043(3) Uani 1 1 d . . .
C4 C 0.8627(3) 0.323(2) 0.5734(14) 0.038(3) Uani 1 1 d . . .
H4 H 0.8589 0.1897 0.6347 0.046 Uiso 1 1 calc R . .
C5 C 0.9020(3) 0.550(3) 0.4233(14) 0.043(3) Uani 1 1 d . . .
C6 C 0.9664(3) 0.536(3) 0.4313(15) 0.049(4) Uani 1 1 d . . .
C7 C 0.6617(3) 0.645(2) 1.0527(13) 0.031(3) Uani 1 1 d . . .
H7 H 0.6819 0.7387 1.0823 0.037 Uiso 1 1 calc R . .
C8 C 0.8746(3) 0.707(3) 0.3856(16) 0.046(4) Uani 1 1 d . . .
H8 H 0.8788 0.8369 0.3215 0.055 Uiso 1 1 calc R . .
C9 C 0.8969(4) 0.362(3) 0.5197(16) 0.051(4) Uani 1 1 d . . .
H9 H 0.9162 0.2612 0.5490 0.061 Uiso 1 1 calc R . .
C10 C 0.6279(3) 0.688(2) 1.1107(13) 0.035(3) Uani 1 1 d . . .
H10 H 0.6254 0.8127 1.1807 0.042 Uiso 1 1 calc R . .
C11 C 0.6005(3) 0.372(2) 0.9604(14) 0.041(3) Uani 1 1 d . . .
H11 H 0.5800 0.2837 0.9285 0.049 Uiso 1 1 calc R . .
C12 C 0.8402(3) 0.674(2) 0.4432(14) 0.037(3) Uani 1 1 d . . .
H12 H 0.8215 0.7819 0.4186 0.044 Uiso 1 1 calc R . .
C14 C 0.9894(4) 0.367(3) 0.3741(18) 0.062(4) Uani 1 1 d . . .
H14 H 0.9822 0.2793 0.2866 0.075 Uiso 1 1 calc R . .
C15 C 0.5134(4) 0.365(3) 1.1241(16) 0.053(4) Uani 1 1 d . . .
H15 H 0.5225 0.2758 1.2080 0.064 Uiso 1 1 calc R . .
C17 C 1.0228(4) 0.328(3) 0.4465(15) 0.061(4) Uani 1 1 d . . .
H17 H 1.0379 0.2079 0.4117 0.073 Uiso 1 1 calc R . .
C18 C 0.4795(4) 0.318(3) 1.0570(15) 0.051(4) Uani 1 1 d . . .
H18 H 0.4655 0.1935 1.0943 0.061 Uiso 1 1 calc R . .
O10 O 0.6978(2) 0.3285(16) 0.7372(9) 0.036(2) Uani 1 1 d . . .
O12 O 0.7425(2) -0.1391(16) 0.7772(9) 0.0332(19) Uani 1 1 d D . .
O9 O 0.7934(2) 0.2517(18) 0.6725(11) 0.050(2) Uani 1 1 d . . .
H12A H 0.7212(12) -0.17(2) 0.743(13) 0.074 Uiso 1 1 d D . .
H12B H 0.758(2) -0.196(19) 0.718(12) 0.074 Uiso 1 1 d D . .
O11 O 0.7583(6) 0.173(4) 0.837(2) 0.151(7) Uani 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
Zn1 O11 1.52(2) . ?
Zn1 O10 1.933(8) . ?
Zn1 O9 1.947(9) . ?
Zn1 O12 1.971(9) . ?
Zn1 O8 1.989(7) 4_565 ?
O2 C2 1.262(14) . ?
O8 C22 1.219(12) . ?
O8 Zn1 1.989(7) 4_566 ?
O4 C5 1.365(14) . ?
O4 C6 1.388(15) . ?
O6 C23 1.362(13) . ?
O6 C3 1.396(15) . ?
C22 O10 1.296(13) . ?
C22 C20 1.486(14) . ?
C23 C11 1.375(17) . ?
C23 C10 1.376(16) . ?
C20 C1 1.391(15) . ?
C20 C7 1.411(15) . ?
C19 C4 1.390(16) . ?
C19 C12 1.394(16) . ?
C19 C2 1.464(15) . ?
C1 C11 1.385(16) . ?
C2 O9 1.227(15) . ?
C3 C18 1.353(19) 3_667 ?
C3 C15 1.39(2) . ?
C4 C9 1.379(17) . ?
C5 C9 1.361(19) . ?
C5 C8 1.363(19) . ?
C6 C17 1.35(2) 3_766 ?
C6 C14 1.38(2) . ?
C7 C10 1.386(15) . ?
C8 C12 1.397(16) . ?
C14 C17 1.37(2) . ?
C15 C18 1.372(19) . ?
C17 C6 1.35(2) 3_766 ?
C18 C3 1.353(19) 3_667 ?

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
O11 Zn1 O10 92.1(8) . . ?
O11 Zn1 O9 70.3(8) . . ?
O10 Zn1 O9 137.2(4) . . ?
O11 Zn1 O12 64.4(8) . . ?
O10 Zn1 O12 104.8(4) . . ?
O9 Zn1 O12 101.9(4) . . ?
O11 Zn1 O8 164.1(8) . 4_565 ?
O10 Zn1 O8 102.2(3) . 4_565 ?
O9 Zn1 O8 102.7(4) . 4_565 ?
O12 Zn1 O8 104.5(4) . 4_565 ?
C22 O8 Zn1 130.9(7) . 4_566 ?
C5 O4 C6 118.5(10) . . ?
C23 O6 C3 117.8(9) . . ?
O8 C22 O10 120.8(10) . . ?
O8 C22 C20 123.7(10) . . ?
O10 C22 C20 115.4(9) . . ?
O6 C23 C11 123.8(11) . . ?
O6 C23 C10 115.7(11) . . ?
C11 C23 C10 120.5(10) . . ?
C1 C20 C7 120.1(9) . . ?
C1 C20 C22 118.8(9) . . ?
C7 C20 C22 121.0(9) . . ?
C4 C19 C12 118.2(10) . . ?
C4 C19 C2 120.7(10) . . ?
C12 C19 C2 121.1(10) . . ?
C11 C1 C20 120.5(10) . . ?
O9 C2 O2 122.2(11) . . ?
O9 C2 C19 118.3(10) . . ?
O2 C2 C19 119.5(11) . . ?
C18 C3 C15 121.7(12) 3_667 . ?
C18 C3 O6 121.0(14) 3_667 . ?
C15 C3 O6 117.0(13) . . ?
C9 C4 C19 121.6(12) . . ?
C9 C5 C8 121.5(12) . . ?
C9 C5 O4 122.6(13) . . ?
C8 C5 O4 115.7(12) . . ?
C17 C6 C14 120.6(13) 3_766 . ?
C17 C6 O4 120.1(15) 3_766 . ?
C14 C6 O4 118.9(14) . . ?
C10 C7 C20 117.7(10) . . ?
C5 C8 C12 119.9(12) . . ?
C5 C9 C4 119.0(13) . . ?
C23 C10 C7 121.6(10) . . ?
C23 C11 C1 119.4(11) . . ?
C19 C12 C8 119.7(11) . . ?
C17 C14 C6 119.7(14) . . ?
C18 C15 C3 118.2(13) . . ?
C6 C17 C14 119.6(14) 3_766 . ?
C3 C18 C15 120.1(14) 3_667 . ?
C22 O10 Zn1 113.1(7) . . ?
C2 O9 Zn1 109.8(8) . . ?

_diffrn_measured_fraction_theta_max 0.998
_diffrn_reflns_theta_full        25.01
_diffrn_measured_fraction_theta_full 0.998
_refine_diff_density_max         0.796
_refine_diff_density_min         -1.195
_refine_diff_density_rms         0.153
