# 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_2
_database_code_depnum_ccdc_archive 'CCDC 999328'
_audit_update_record             
;
2014-04-24 deposited with the CCDC.
2015-03-23 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 H19 O17 Zn2.50'
_chemical_formula_weight         610.71

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           Triclinic
_symmetry_space_group_name_H-M   P-1

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

_cell_length_a                   7.7407(4)
_cell_length_b                   10.0073(6)
_cell_length_c                   12.4336(7)
_cell_angle_alpha                89.7320(10)
_cell_angle_beta                 89.8840(10)
_cell_angle_gamma                84.9460(10)
_cell_volume                     959.39(9)
_cell_formula_units_Z            2
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    7045
_cell_measurement_theta_min      2.61
_cell_measurement_theta_max      28.37

_exptl_crystal_description       block
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.26
_exptl_crystal_size_mid          0.25
_exptl_crystal_size_min          0.20
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    2.114
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             616
_exptl_absorpt_coefficient_mu    3.203
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.4898
_exptl_absorpt_correction_T_max  0.5668
_exptl_absorpt_process_details   sadabs

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      296(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            7400
_diffrn_reflns_av_R_equivalents  0.0108
_diffrn_reflns_av_sigmaI/netI    0.0136
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_theta_min         2.62
_diffrn_reflns_theta_max         25.50
_reflns_number_total             3537
_reflns_number_gt                3408
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'

_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)+(0.0332P)²+0.7712P] 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         3537
_refine_ls_number_parameters     292
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0226
_refine_ls_R_factor_gt           0.0219
_refine_ls_wR_factor_ref         0.0590
_refine_ls_wR_factor_gt          0.0586
_refine_ls_goodness_of_fit_ref   1.090
_refine_ls_restrained_S_all      1.090
_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
C1 C 0.3298(2) 0.3519(2) 0.16645(16) 0.0166(4) Uani 1 1 d . . .
C2 C 0.2936(3) 0.4392(2) 0.06865(15) 0.0163(4) Uani 1 1 d . . .
C3 C 0.2222(3) 0.5713(2) 0.08027(16) 0.0180(4) Uani 1 1 d . . .
H3 H 0.1970 0.6064 0.1482 0.022 Uiso 1 1 calc R . .
C4 C 0.1895(2) 0.64950(19) -0.01136(16) 0.0157(4) Uani 1 1 d . . .
C5 C 0.2346(2) 0.59655(19) -0.11244(15) 0.0152(4) Uani 1 1 d . . .
C6 C 0.2984(3) 0.4625(2) -0.12261(15) 0.0167(4) Uani 1 1 d . . .
C7 C 0.3285(3) 0.3829(2) -0.03191(16) 0.0182(4) Uani 1 1 d . . .
H7 H 0.3712 0.2935 -0.0382 0.022 Uiso 1 1 calc R . .
C8 C 0.0813(3) 0.8465(2) 0.08534(17) 0.0197(4) Uani 1 1 d . . .
H8A H 0.0534 0.7833 0.1407 0.024 Uiso 1 1 calc R . .
H8B H -0.0165 0.9134 0.0782 0.024 Uiso 1 1 calc R . .
C9 C 0.2409(3) 0.9146(2) 0.11919(17) 0.0210(4) Uani 1 1 d . . .
C10 C 0.0495(3) 0.6779(2) -0.24976(18) 0.0261(5) Uani 1 1 d . . .
H10A H -0.0382 0.6995 -0.1953 0.031 Uiso 1 1 calc R . .
H10B H 0.0331 0.5897 -0.2779 0.031 Uiso 1 1 calc R . .
C11 C 0.0309(3) 0.7801(2) -0.33898(17) 0.0207(4) Uani 1 1 d . . .
C12 C 0.3844(3) 0.2820(2) -0.23792(17) 0.0274(5) Uani 1 1 d . . .
H12A H 0.3078 0.2278 -0.1983 0.033 Uiso 1 1 calc R . .
H12B H 0.4994 0.2663 -0.2070 0.033 Uiso 1 1 calc R . .
C13 C 0.3906(3) 0.2391(2) -0.35438(16) 0.0184(4) Uani 1 1 d . . .
O1 O 0.3629(2) 0.22887(15) 0.15069(12) 0.0281(4) Uani 1 1 d . . .
O2 O 0.31844(19) 0.40876(14) 0.25664(11) 0.0205(3) Uani 1 1 d . . .
O3 O 0.10870(19) 0.77739(14) -0.01416(11) 0.0208(3) Uani 1 1 d . . .
O4 O 0.2393(2) 0.95691(16) 0.21567(12) 0.0282(3) Uani 1 1 d . . .
O5 O 0.3603(2) 0.9265(2) 0.05559(14) 0.0379(4) Uani 1 1 d . . .
O6 O 0.21820(17) 0.67723(14) -0.20314(11) 0.0168(3) Uani 1 1 d . . .
O7 O 0.1395(2) 0.86306(19) -0.34570(15) 0.0391(5) Uani 1 1 d . . .
O8 O -0.1007(2) 0.77821(16) -0.40010(13) 0.0257(3) Uani 1 1 d . . .
O9 O 0.3253(2) 0.41926(14) -0.22676(11) 0.0222(3) Uani 1 1 d . . .
O10 O 0.3371(2) 0.31858(16) -0.42615(12) 0.0328(4) Uani 1 1 d . . .
O11 O 0.4505(2) 0.11977(15) -0.36640(12) 0.0311(4) Uani 1 1 d . . .
O12 O 0.47736(17) 0.14877(13) 0.37993(10) 0.0147(3) Uani 1 1 d . . .
H12 H 0.5772 0.1689 0.3748 0.022 Uiso 1 1 d R . .
O13 O 0.16988(15) 0.51351(11) 0.44750(9) 0.0284(3) Uani 1 1 d . . .
H1W H 0.1453 0.5766 0.4004 0.043 Uiso 1 1 d R . .
H2W H 0.0882 0.4743 0.4429 0.043 Uiso 1 1 d R . .
O14 O 0.57994(15) 0.41146(11) 0.40587(9) 0.0298(4) Uani 1 1 d R . .
H3W H 0.6145 0.4180 0.3438 0.045 Uiso 1 1 d R . .
H4W H 0.6325 0.4552 0.4488 0.045 Uiso 1 1 d R . .
O15 O 0.6680(2) 0.03675(16) 0.16412(12) 0.0259(3) Uani 1 1 d . . .
H5W H 0.7357 0.0865 0.1914 0.039 Uiso 1 1 d R . .
H6W H 0.6549 0.0524 0.0997 0.039 Uiso 1 1 d R . .
O16 O 0.2333(2) -0.02042(16) 0.47574(13) 0.0295(4) Uani 1 1 d . . .
H7W H 0.1852 0.0512 0.4547 0.044 Uiso 1 1 d R . .
H8W H 0.1892 -0.0463 0.5325 0.044 Uiso 1 1 d R . .
O17 O 0.0666(3) 0.7530(2) 0.34752(18) 0.0578(6) Uani 1 1 d . . .
H9W H 0.1663 0.7724 0.3508 0.087 Uiso 1 1 d R . .
H10W H 0.0049 0.7770 0.3986 0.087 Uiso 1 1 d R . .
Zn1 Zn 0.5000 0.0000 0.5000 0.01628(9) Uani 1 2 d S . .
Zn2 Zn 0.32410(3) 0.32410(2) 0.405532(17) 0.01650(8) Uani 1 1 d . . .
Zn3 Zn 0.43729(3) 0.06336(2) 0.239257(18) 0.01941(8) 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
C1 O1 1.252(3) . ?
C1 O2 1.259(3) . ?
C1 C2 1.506(3) . ?
C2 C7 1.390(3) . ?
C2 C3 1.395(3) . ?
C3 C4 1.390(3) . ?
C3 H3 0.9300 . ?
C4 O3 1.374(2) . ?
C4 C5 1.398(3) . ?
C5 O6 1.383(2) . ?
C5 C6 1.394(3) . ?
C6 O9 1.377(2) . ?
C6 C7 1.386(3) . ?
C7 H7 0.9300 . ?
C8 O3 1.426(2) . ?
C8 C9 1.523(3) . ?
C8 H8A 0.9700 . ?
C8 H8B 0.9700 . ?
C9 O5 1.228(3) . ?
C9 O4 1.274(3) . ?
C10 O6 1.429(2) . ?
C10 C11 1.504(3) . ?
C10 H10A 0.9700 . ?
C10 H10B 0.9700 . ?
C11 O7 1.235(3) . ?
C11 O8 1.273(3) . ?
C12 O9 1.417(2) . ?
C12 C13 1.512(3) . ?
C12 H12A 0.9700 . ?
C12 H12B 0.9700 . ?
C13 O10 1.240(3) . ?
C13 O11 1.252(3) . ?
O1 Zn3 2.0261(15) . ?
O2 Zn2 2.0313(14) . ?
O4 Zn3 1.9653(16) 1_565 ?
O8 Zn2 2.0871(15) 2_565 ?
O10 Zn2 2.0957(15) 1_554 ?
O11 Zn1 2.0683(15) 1_554 ?
O12 Zn3 1.9872(13) . ?
O12 Zn2 2.0553(13) . ?
O12 Zn1 2.1001(13) . ?
O12 H12 0.8178 . ?
O13 Zn2 2.2132(12) . ?
O13 H1W 0.8679 . ?
O13 H2W 0.7752 . ?
O14 Zn2 2.2342(12) . ?
O14 H3W 0.8200 . ?
O14 H4W 0.8226 . ?
O15 Zn3 2.0113(15) . ?
O15 H5W 0.8279 . ?
O15 H6W 0.8200 . ?
O16 Zn1 2.1149(16) . ?
O16 H7W 0.8200 . ?
O16 H8W 0.8338 . ?
O17 H9W 0.8140 . ?
O17 H10W 0.8178 . ?
Zn1 O11 2.0683(15) 2_655 ?
Zn1 O11 2.0683(15) 1_556 ?
Zn1 O12 2.1000(13) 2_656 ?
Zn1 O16 2.1149(16) 2_656 ?
Zn2 O8 2.0872(15) 2_565 ?
Zn2 O10 2.0957(15) 1_556 ?
Zn3 O4 1.9653(16) 1_545 ?

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 C1 O2 126.00(18) . . ?
O1 C1 C2 116.91(18) . . ?
O2 C1 C2 117.04(17) . . ?
C7 C2 C3 121.82(18) . . ?
C7 C2 C1 118.08(18) . . ?
C3 C2 C1 120.08(18) . . ?
C4 C3 C2 118.90(18) . . ?
C4 C3 H3 120.5 . . ?
C2 C3 H3 120.5 . . ?
O3 C4 C3 126.00(18) . . ?
O3 C4 C5 114.28(17) . . ?
C3 C4 C5 119.68(18) . . ?
O6 C5 C6 119.42(17) . . ?
O6 C5 C4 120.23(17) . . ?
C6 C5 C4 120.35(18) . . ?
O9 C6 C7 124.78(18) . . ?
O9 C6 C5 114.98(17) . . ?
C7 C6 C5 120.24(18) . . ?
C6 C7 C2 118.77(18) . . ?
C6 C7 H7 120.6 . . ?
C2 C7 H7 120.6 . . ?
O3 C8 C9 111.64(17) . . ?
O3 C8 H8A 109.3 . . ?
C9 C8 H8A 109.3 . . ?
O3 C8 H8B 109.3 . . ?
C9 C8 H8B 109.3 . . ?
H8A C8 H8B 108.0 . . ?
O5 C9 O4 124.0(2) . . ?
O5 C9 C8 120.67(19) . . ?
O4 C9 C8 115.36(19) . . ?
O6 C10 C11 109.60(17) . . ?
O6 C10 H10A 109.8 . . ?
C11 C10 H10A 109.8 . . ?
O6 C10 H10B 109.8 . . ?
C11 C10 H10B 109.8 . . ?
H10A C10 H10B 108.2 . . ?
O7 C11 O8 124.40(19) . . ?
O7 C11 C10 118.25(18) . . ?
O8 C11 C10 117.29(18) . . ?
O9 C12 C13 111.87(17) . . ?
O9 C12 H12A 109.2 . . ?
C13 C12 H12A 109.2 . . ?
O9 C12 H12B 109.2 . . ?
C13 C12 H12B 109.2 . . ?
H12A C12 H12B 107.9 . . ?
O10 C13 O11 126.77(19) . . ?
O10 C13 C12 120.34(18) . . ?
O11 C13 C12 112.88(18) . . ?
C1 O1 Zn3 137.41(14) . . ?
C1 O2 Zn2 128.71(13) . . ?
C4 O3 C8 117.92(15) . . ?
C9 O4 Zn3 109.84(14) . 1_565 ?
C5 O6 C10 111.75(15) . . ?
C11 O8 Zn2 136.66(14) . 2_565 ?
C6 O9 C12 115.31(15) . . ?
C13 O10 Zn2 138.21(14) . 1_554 ?
C13 O11 Zn1 133.32(14) . 1_554 ?
Zn3 O12 Zn2 113.96(6) . . ?
Zn3 O12 Zn1 109.03(6) . . ?
Zn2 O12 Zn1 119.96(6) . . ?
Zn3 O12 H12 103.1 . . ?
Zn2 O12 H12 106.7 . . ?
Zn1 O12 H12 101.9 . . ?
Zn2 O13 H1W 122.0 . . ?
Zn2 O13 H2W 87.2 . . ?
H1W O13 H2W 100.4 . . ?
Zn2 O14 H3W 109.4 . . ?
Zn2 O14 H4W 135.2 . . ?
H3W O14 H4W 113.0 . . ?
Zn3 O15 H5W 109.3 . . ?
Zn3 O15 H6W 109.5 . . ?
H5W O15 H6W 111.3 . . ?
Zn1 O16 H7W 109.5 . . ?
Zn1 O16 H8W 109.7 . . ?
H7W O16 H8W 111.8 . . ?
H9W O17 H10W 115.4 . . ?
O11 Zn1 O11 180.00(5) 2_655 1_556 ?
O11 Zn1 O12 99.19(6) 2_655 2_656 ?
O11 Zn1 O12 80.81(6) 1_556 2_656 ?
O11 Zn1 O12 80.81(6) 2_655 . ?
O11 Zn1 O12 99.19(6) 1_556 . ?
O12 Zn1 O12 180.00(5) 2_656 . ?
O11 Zn1 O16 92.31(7) 2_655 2_656 ?
O11 Zn1 O16 87.69(7) 1_556 2_656 ?
O12 Zn1 O16 86.82(6) 2_656 2_656 ?
O12 Zn1 O16 93.18(6) . 2_656 ?
O11 Zn1 O16 87.69(7) 2_655 . ?
O11 Zn1 O16 92.31(7) 1_556 . ?
O12 Zn1 O16 93.18(6) 2_656 . ?
O12 Zn1 O16 86.82(6) . . ?
O16 Zn1 O16 180.0 2_656 . ?
O2 Zn2 O12 101.67(6) . . ?
O2 Zn2 O8 100.56(6) . 2_565 ?
O12 Zn2 O8 90.94(6) . 2_565 ?
O2 Zn2 O10 156.70(6) . 1_556 ?
O12 Zn2 O10 96.45(6) . 1_556 ?
O8 Zn2 O10 93.62(7) 2_565 1_556 ?
O2 Zn2 O13 82.51(5) . . ?
O12 Zn2 O13 174.87(5) . . ?
O8 Zn2 O13 91.21(6) 2_565 . ?
O10 Zn2 O13 78.76(5) 1_556 . ?
O2 Zn2 O14 80.16(5) . . ?
O12 Zn2 O14 82.53(5) . . ?
O8 Zn2 O14 173.43(5) 2_565 . ?
O10 Zn2 O14 87.87(6) 1_556 . ?
O13 Zn2 O14 95.36(4) . . ?
O4 Zn3 O12 121.82(6) 1_545 . ?
O4 Zn3 O15 125.67(7) 1_545 . ?
O12 Zn3 O15 107.18(6) . . ?
O4 Zn3 O1 100.44(7) 1_545 . ?
O12 Zn3 O1 99.73(6) . . ?
O15 Zn3 O1 92.46(7) . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
O1 C1 C2 C7 -11.0(3) . . . . ?
O2 C1 C2 C7 171.26(18) . . . . ?
O1 C1 C2 C3 167.08(19) . . . . ?
O2 C1 C2 C3 -10.6(3) . . . . ?
C7 C2 C3 C4 -1.7(3) . . . . ?
C1 C2 C3 C4 -179.74(18) . . . . ?
C2 C3 C4 O3 175.08(18) . . . . ?
C2 C3 C4 C5 -2.5(3) . . . . ?
O3 C4 C5 O6 8.4(3) . . . . ?
C3 C4 C5 O6 -173.74(17) . . . . ?
O3 C4 C5 C6 -172.35(17) . . . . ?
C3 C4 C5 C6 5.5(3) . . . . ?
O6 C5 C6 O9 -5.7(3) . . . . ?
C4 C5 C6 O9 175.08(17) . . . . ?
O6 C5 C6 C7 174.96(17) . . . . ?
C4 C5 C6 C7 -4.3(3) . . . . ?
O9 C6 C7 C2 -179.21(18) . . . . ?
C5 C6 C7 C2 0.1(3) . . . . ?
C3 C2 C7 C6 2.9(3) . . . . ?
C1 C2 C7 C6 -179.00(18) . . . . ?
O3 C8 C9 O5 12.7(3) . . . . ?
O3 C8 C9 O4 -167.47(17) . . . . ?
O6 C10 C11 O7 -13.8(3) . . . . ?
O6 C10 C11 O8 168.88(19) . . . . ?
O9 C12 C13 O10 -4.3(3) . . . . ?
O9 C12 C13 O11 176.7(2) . . . . ?
O2 C1 O1 Zn3 -8.0(4) . . . . ?
C2 C1 O1 Zn3 174.54(15) . . . . ?
O1 C1 O2 Zn2 -6.8(3) . . . . ?
C2 C1 O2 Zn2 170.65(13) . . . . ?
C3 C4 O3 C8 11.4(3) . . . . ?
C5 C4 O3 C8 -170.91(17) . . . . ?
C9 C8 O3 C4 84.3(2) . . . . ?
O5 C9 O4 Zn3 7.7(3) . . . 1_565 ?
C8 C9 O4 Zn3 -172.10(14) . . . 1_565 ?
C6 C5 O6 C10 92.1(2) . . . . ?
C4 C5 O6 C10 -88.6(2) . . . . ?
C11 C10 O6 C5 172.75(17) . . . . ?
O7 C11 O8 Zn2 -170.86(18) . . . 2_565 ?
C10 C11 O8 Zn2 6.3(3) . . . 2_565 ?
C7 C6 O9 C12 1.4(3) . . . . ?
C5 C6 O9 C12 -177.93(19) . . . . ?
C13 C12 O9 C6 173.35(18) . . . . ?
O11 C13 O10 Zn2 -5.6(4) . . . 1_554 ?
C12 C13 O10 Zn2 175.59(18) . . . 1_554 ?
O10 C13 O11 Zn1 2.8(4) . . . 1_554 ?
C12 C13 O11 Zn1 -178.31(16) . . . 1_554 ?
Zn3 O12 Zn1 O11 19.43(7) . . . 2_655 ?
Zn2 O12 Zn1 O11 153.44(9) . . . 2_655 ?
Zn3 O12 Zn1 O11 -160.57(7) . . . 1_556 ?
Zn2 O12 Zn1 O11 -26.56(9) . . . 1_556 ?
Zn3 O12 Zn1 O12 -30(84) . . . 2_656 ?
Zn2 O12 Zn1 O12 104(84) . . . 2_656 ?
Zn3 O12 Zn1 O16 111.26(7) . . . 2_656 ?
Zn2 O12 Zn1 O16 -114.74(8) . . . 2_656 ?
Zn3 O12 Zn1 O16 -68.74(7) . . . . ?
Zn2 O12 Zn1 O16 65.26(8) . . . . ?
C1 O2 Zn2 O12 29.52(17) . . . . ?
C1 O2 Zn2 O8 -63.66(17) . . . 2_565 ?
C1 O2 Zn2 O10 169.82(17) . . . 1_556 ?
C1 O2 Zn2 O13 -153.50(17) . . . . ?
C1 O2 Zn2 O14 109.70(17) . . . . ?
Zn3 O12 Zn2 O2 -38.15(8) . . . . ?
Zn1 O12 Zn2 O2 -170.07(7) . . . . ?
Zn3 O12 Zn2 O8 62.83(7) . . . 2_565 ?
Zn1 O12 Zn2 O8 -69.09(8) . . . 2_565 ?
Zn3 O12 Zn2 O10 156.58(8) . . . 1_556 ?
Zn1 O12 Zn2 O10 24.66(9) . . . 1_556 ?
Zn3 O12 Zn2 O13 177.6(5) . . . . ?
Zn1 O12 Zn2 O13 45.6(6) . . . . ?
Zn3 O12 Zn2 O14 -116.43(7) . . . . ?
Zn1 O12 Zn2 O14 111.65(7) . . . . ?
Zn2 O12 Zn3 O4 -79.14(9) . . . 1_545 ?
Zn1 O12 Zn3 O4 57.86(9) . . . 1_545 ?
Zn2 O12 Zn3 O15 125.35(7) . . . . ?
Zn1 O12 Zn3 O15 -97.64(7) . . . . ?
Zn2 O12 Zn3 O1 29.69(8) . . . . ?
Zn1 O12 Zn3 O1 166.70(7) . . . . ?
C1 O1 Zn3 O4 119.0(2) . . . 1_545 ?
C1 O1 Zn3 O12 -6.1(2) . . . . ?
C1 O1 Zn3 O15 -114.0(2) . . . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
O12 H12 O7 0.82 2.22 2.988(2) 157.0 2_665
O13 H1W O17 0.87 1.93 2.751(2) 157.5 .
O13 H2W O13 0.78 2.41 2.967(2) 129.8 2_566
O13 H2W O8 0.78 2.58 3.074(2) 123.4 2_565
O14 H3W O9 0.82 2.26 2.9232(18) 138.5 2_665
O14 H3W O6 0.82 2.33 3.0567(18) 147.8 2_665
O14 H4W O13 0.82 2.05 2.814(2) 154.8 2_666
O14 H4W O10 0.82 2.31 2.844(2) 122.9 2_665
O15 H5W O7 0.83 2.23 2.936(2) 143.4 2_665
O15 H5W O6 0.83 2.43 3.108(2) 140.2 2_665
O15 H6W O5 0.82 1.94 2.761(2) 174.2 2_665
O16 H7W O8 0.82 1.90 2.712(2) 173.1 2_565
O16 H8W O7 0.83 1.82 2.633(2) 165.0 1_546
O17 H9W O4 0.81 2.59 3.013(3) 114.0 .
O17 H10W O8 0.82 2.63 3.394(3) 155.9 1_556

_diffrn_measured_fraction_theta_max 0.991
_diffrn_reflns_theta_full        25.50
_diffrn_measured_fraction_theta_full 0.991
_refine_diff_density_max         0.434
_refine_diff_density_min         -0.724
_refine_diff_density_rms         0.140
####################################################################### 
# 
# 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 999329'
_audit_update_record             
;
2014-04-24 deposited with the CCDC.
2015-03-23 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 H11 O13 Zn2.50'
_chemical_formula_weight         538.64

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           Monoclinic
_symmetry_space_group_name_H-M   P2(1)/c

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                   8.0745(3)
_cell_length_b                   8.5747(4)
_cell_length_c                   22.7033(10)
_cell_angle_alpha                90.00
_cell_angle_beta                 92.1660(10)
_cell_angle_gamma                90.00
_cell_volume                     1570.77(12)
_cell_formula_units_Z            4
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    8441
_cell_measurement_theta_min      2.54
_cell_measurement_theta_max      29.36

_exptl_crystal_description       block
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.24
_exptl_crystal_size_mid          0.21
_exptl_crystal_size_min          0.20
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    2.278
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1072
_exptl_absorpt_coefficient_mu    3.878
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.4563
_exptl_absorpt_correction_T_max  0.5110
_exptl_absorpt_process_details   sadabs

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      296(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            13626
_diffrn_reflns_av_R_equivalents  0.0188
_diffrn_reflns_av_sigmaI/netI    0.0163
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_l_min       -29
_diffrn_reflns_limit_l_max       29
_diffrn_reflns_theta_min         2.52
_diffrn_reflns_theta_max         27.50
_reflns_number_total             3606
_reflns_number_gt                3326
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'

_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)+(0.0313P)²+1.8512P] 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         3606
_refine_ls_number_parameters     247
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0276
_refine_ls_R_factor_gt           0.0247
_refine_ls_wR_factor_ref         0.0646
_refine_ls_wR_factor_gt          0.0632
_refine_ls_goodness_of_fit_ref   1.073
_refine_ls_restrained_S_all      1.073
_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
C1 C 0.4950(3) 0.2108(2) 0.12947(9) 0.0175(4) Uani 1 1 d . . .
C2 C 0.3844(3) 0.2763(2) 0.17461(9) 0.0172(4) Uani 1 1 d . . .
C3 C 0.4131(3) 0.2366(3) 0.23366(9) 0.0183(4) Uani 1 1 d . . .
H3 H 0.4950 0.1651 0.2449 0.022 Uiso 1 1 calc R . .
C4 C 0.3164(3) 0.3066(2) 0.27510(9) 0.0166(4) Uani 1 1 d . . .
C5 C 0.1915(2) 0.4122(2) 0.25865(9) 0.0167(4) Uani 1 1 d . . .
C6 C 0.1611(3) 0.4472(2) 0.19920(9) 0.0176(4) Uani 1 1 d . . .
C7 C 0.2591(3) 0.3789(3) 0.15714(9) 0.0186(4) Uani 1 1 d . . .
H7 H 0.2407 0.4021 0.1174 0.022 Uiso 1 1 calc R . .
C8 C 0.4685(3) 0.1902(3) 0.35619(10) 0.0228(5) Uani 1 1 d . . .
H8A H 0.5677 0.2192 0.3360 0.027 Uiso 1 1 calc R . .
H8B H 0.4472 0.0803 0.3493 0.027 Uiso 1 1 calc R . .
C9 C 0.4914(3) 0.2212(2) 0.42137(9) 0.0186(4) Uani 1 1 d . . .
C10 C -0.0622(3) 0.4672(3) 0.30766(10) 0.0255(5) Uani 1 1 d . . .
H10A H -0.0974 0.3725 0.2874 0.031 Uiso 1 1 calc R . .
H10B H -0.1196 0.5546 0.2890 0.031 Uiso 1 1 calc R . .
C11 C -0.1044(3) 0.4579(3) 0.37209(10) 0.0205(4) Uani 1 1 d . . .
C12 C -0.0082(3) 0.5788(3) 0.12661(10) 0.0214(4) Uani 1 1 d . . .
H12A H 0.0912 0.5896 0.1043 0.026 Uiso 1 1 calc R . .
H12B H -0.0691 0.6761 0.1233 0.026 Uiso 1 1 calc R . .
C13 C -0.1136(3) 0.4497(3) 0.09960(11) 0.0246(5) Uani 1 1 d . . .
O1 O 0.59205(19) 0.10471(18) 0.14599(7) 0.0209(3) Uani 1 1 d . . .
O2 O 0.4846(2) 0.2692(2) 0.07830(7) 0.0268(4) Uani 1 1 d . . .
O3 O 0.33145(19) 0.28091(18) 0.33489(6) 0.0200(3) Uani 1 1 d . . .
O4 O 0.5963(2) 0.1353(2) 0.44791(7) 0.0259(4) Uani 1 1 d . . .
O5 O 0.4119(2) 0.3285(2) 0.44484(7) 0.0244(3) Uani 1 1 d . . .
O6 O 0.11331(19) 0.48665(19) 0.30363(7) 0.0210(3) Uani 1 1 d . . .
O7 O 0.01815(18) 0.45116(19) 0.41047(7) 0.0205(3) Uani 1 1 d . . .
O8 O -0.2495(2) 0.4555(3) 0.38469(9) 0.0376(5) Uani 1 1 d . . .
O9 O 0.0389(2) 0.5534(2) 0.18707(7) 0.0239(3) Uani 1 1 d . . .
O10 O -0.1386(3) 0.3275(2) 0.12490(10) 0.0442(5) Uani 1 1 d . . .
O12 O 0.23091(18) 0.59407(18) 0.48340(7) 0.0192(3) Uani 1 1 d . . .
H12 H 0.2947 0.5602 0.5093 0.023 Uiso 1 1 d R . .
O11 O -0.1774(2) 0.4835(2) 0.04840(9) 0.034 Uani 1 1 d . . .
O13 O -0.1247(2) 0.7250(2) 0.48005(8) 0.030 Uani 1 1 d . . .
H2W H -0.1233 0.8053 0.5001 0.045 Uiso 1 1 d R . .
H1W H -0.2211 0.6950 0.4731 0.045 Uiso 1 1 d R . .
Zn1 Zn 0.0000 0.5000 0.5000 0.02478(10) Uani 1 2 d S . .
Zn2 Zn 0.26081(3) 0.48538(3) 0.401661(11) 0.01992(8) Uani 1 1 d . . .
Zn3 Zn 0.32360(3) 0.80550(3) 0.472060(11) 0.01941(7) 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
C1 O1 1.249(3) . ?
C1 O2 1.265(3) . ?
C1 C2 1.494(3) . ?
C2 C7 1.387(3) . ?
C2 C3 1.394(3) . ?
C3 C4 1.383(3) . ?
C3 H3 0.9300 . ?
C4 O3 1.376(2) . ?
C4 C5 1.396(3) . ?
C5 O6 1.377(2) . ?
C5 C6 1.395(3) . ?
C6 O9 1.364(3) . ?
C6 C7 1.392(3) . ?
C7 H7 0.9300 . ?
C8 O3 1.422(3) . ?
C8 C9 1.508(3) . ?
C8 H8A 0.9700 . ?
C8 H8B 0.9700 . ?
C9 O5 1.252(3) . ?
C9 O4 1.259(3) . ?
C10 O6 1.433(3) . ?
C10 C11 1.517(3) . ?
C10 H10A 0.9700 . ?
C10 H10B 0.9700 . ?
C11 O8 1.217(3) . ?
C11 O7 1.295(3) . ?
C12 O9 1.427(3) . ?
C12 C13 1.512(3) . ?
C12 H12A 0.9700 . ?
C12 H12B 0.9700 . ?
C13 O10 1.216(3) . ?
C13 O11 1.287(3) . ?
O1 Zn2 1.9302(15) 2_645 ?
O2 Zn3 1.9842(16) 2_645 ?
O3 Zn2 2.4006(15) . ?
O4 Zn3 1.9718(16) 3_666 ?
O5 Zn2 2.0421(16) . ?
O6 Zn2 2.4844(16) . ?
O7 Zn2 1.9987(15) . ?
O7 Zn1 2.0859(15) . ?
O12 Zn3 1.9819(15) . ?
O12 Zn1 2.0789(14) . ?
O12 Zn2 2.0988(15) . ?
O12 H12 0.8202 . ?
O11 Zn3 1.9739(18) 2_545 ?
O13 Zn1 2.2152(18) . ?
O13 H2W 0.8258 . ?
O13 H1W 0.8286 . ?
Zn1 O12 2.0789(15) 3_566 ?
Zn1 O7 2.0859(15) 3_566 ?
Zn1 O13 2.2152(18) 3_566 ?
Zn1 Zn2 3.1290(3) . ?
Zn1 Zn2 3.1290(3) 3_566 ?
Zn2 O1 1.9303(15) 2_655 ?
Zn3 O4 1.9719(16) 3_666 ?
Zn3 O11 1.9739(18) 2 ?
Zn3 O2 1.9841(16) 2_655 ?

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 C1 O2 125.67(19) . . ?
O1 C1 C2 116.91(19) . . ?
O2 C1 C2 117.40(19) . . ?
C7 C2 C3 121.54(19) . . ?
C7 C2 C1 119.39(19) . . ?
C3 C2 C1 119.04(19) . . ?
C4 C3 C2 118.06(19) . . ?
C4 C3 H3 121.0 . . ?
C2 C3 H3 121.0 . . ?
O3 C4 C3 124.78(19) . . ?
O3 C4 C5 113.83(18) . . ?
C3 C4 C5 121.39(19) . . ?
O6 C5 C6 123.30(19) . . ?
O6 C5 C4 116.68(18) . . ?
C6 C5 C4 119.80(18) . . ?
O9 C6 C7 124.64(19) . . ?
O9 C6 C5 115.98(18) . . ?
C7 C6 C5 119.32(19) . . ?
C2 C7 C6 119.9(2) . . ?
C2 C7 H7 120.1 . . ?
C6 C7 H7 120.1 . . ?
O3 C8 C9 107.59(17) . . ?
O3 C8 H8A 110.2 . . ?
C9 C8 H8A 110.2 . . ?
O3 C8 H8B 110.2 . . ?
C9 C8 H8B 110.2 . . ?
H8A C8 H8B 108.5 . . ?
O5 C9 O4 124.9(2) . . ?
O5 C9 C8 120.10(19) . . ?
O4 C9 C8 114.95(19) . . ?
O6 C10 C11 109.06(18) . . ?
O6 C10 H10A 109.9 . . ?
C11 C10 H10A 109.9 . . ?
O6 C10 H10B 109.9 . . ?
C11 C10 H10B 109.9 . . ?
H10A C10 H10B 108.3 . . ?
O8 C11 O7 124.0(2) . . ?
O8 C11 C10 118.8(2) . . ?
O7 C11 C10 117.24(18) . . ?
O9 C12 C13 113.83(19) . . ?
O9 C12 H12A 108.8 . . ?
C13 C12 H12A 108.8 . . ?
O9 C12 H12B 108.8 . . ?
C13 C12 H12B 108.8 . . ?
H12A C12 H12B 107.7 . . ?
O10 C13 O11 123.6(2) . . ?
O10 C13 C12 122.7(2) . . ?
O11 C13 C12 113.7(2) . . ?
C1 O1 Zn2 127.62(14) . 2_645 ?
C1 O2 Zn3 124.42(14) . 2_645 ?
C4 O3 C8 117.50(16) . . ?
C4 O3 Zn2 119.45(12) . . ?
C8 O3 Zn2 112.64(12) . . ?
C9 O4 Zn3 118.82(14) . 3_666 ?
C9 O5 Zn2 125.89(14) . . ?
C5 O6 C10 118.38(17) . . ?
C5 O6 Zn2 116.39(13) . . ?
C10 O6 Zn2 112.58(13) . . ?
C11 O7 Zn2 130.78(14) . . ?
C11 O7 Zn1 124.54(14) . . ?
Zn2 O7 Zn1 99.98(7) . . ?
C6 O9 C12 117.41(17) . . ?
Zn3 O12 Zn1 136.40(8) . . ?
Zn3 O12 Zn2 103.57(6) . . ?
Zn1 O12 Zn2 97.00(6) . . ?
Zn3 O12 H12 100.8 . . ?
Zn1 O12 H12 106.0 . . ?
Zn2 O12 H12 112.7 . . ?
C13 O11 Zn3 104.72(16) . 2_545 ?
Zn1 O13 H2W 128.1 . . ?
Zn1 O13 H1W 100.7 . . ?
H2W O13 H1W 110.9 . . ?
O12 Zn1 O12 180.0 3_566 . ?
O12 Zn1 O7 101.26(6) 3_566 . ?
O12 Zn1 O7 78.74(6) . . ?
O12 Zn1 O7 78.74(6) 3_566 3_566 ?
O12 Zn1 O7 101.26(6) . 3_566 ?
O7 Zn1 O7 180.00(8) . 3_566 ?
O12 Zn1 O13 88.34(6) 3_566 . ?
O12 Zn1 O13 91.66(6) . . ?
O7 Zn1 O13 91.36(6) . . ?
O7 Zn1 O13 88.64(6) 3_566 . ?
O12 Zn1 O13 91.66(6) 3_566 3_566 ?
O12 Zn1 O13 88.34(6) . 3_566 ?
O7 Zn1 O13 88.64(6) . 3_566 ?
O7 Zn1 O13 91.36(6) 3_566 3_566 ?
O13 Zn1 O13 179.999(1) . 3_566 ?
O12 Zn1 Zn2 138.26(4) 3_566 . ?
O12 Zn1 Zn2 41.74(4) . . ?
O7 Zn1 Zn2 38.98(4) . . ?
O7 Zn1 Zn2 141.02(4) 3_566 . ?
O13 Zn1 Zn2 101.66(5) . . ?
O13 Zn1 Zn2 78.34(4) 3_566 . ?
O12 Zn1 Zn2 41.74(4) 3_566 3_566 ?
O12 Zn1 Zn2 138.26(4) . 3_566 ?
O7 Zn1 Zn2 141.02(4) . 3_566 ?
O7 Zn1 Zn2 38.98(4) 3_566 3_566 ?
O13 Zn1 Zn2 78.34(5) . 3_566 ?
O13 Zn1 Zn2 101.66(4) 3_566 3_566 ?
Zn2 Zn1 Zn2 180.0 . 3_566 ?
O1 Zn2 O7 139.50(7) 2_655 . ?
O1 Zn2 O5 104.42(7) 2_655 . ?
O7 Zn2 O5 115.18(7) . . ?
O1 Zn2 O12 110.73(6) 2_655 . ?
O7 Zn2 O12 80.26(6) . . ?
O5 Zn2 O12 87.41(6) . . ?
O1 Zn2 O3 82.37(6) 2_655 . ?
O7 Zn2 O3 102.31(6) . . ?
O5 Zn2 O3 70.73(6) . . ?
O12 Zn2 O3 157.03(6) . . ?
O1 Zn2 O6 77.29(6) 2_655 . ?
O7 Zn2 O6 69.62(6) . . ?
O5 Zn2 O6 133.67(6) . . ?
O12 Zn2 O6 136.30(6) . . ?
O3 Zn2 O6 63.56(5) . . ?
O1 Zn2 Zn1 145.46(5) 2_655 . ?
O7 Zn2 Zn1 41.04(4) . . ?
O5 Zn2 Zn1 95.16(5) . . ?
O12 Zn2 Zn1 41.26(4) . . ?
O3 Zn2 Zn1 131.47(4) . . ?
O6 Zn2 Zn1 109.04(4) . . ?
O4 Zn3 O11 100.97(7) 3_666 2 ?
O4 Zn3 O12 103.17(7) 3_666 . ?
O11 Zn3 O12 120.83(8) 2 . ?
O4 Zn3 O2 109.60(7) 3_666 2_655 ?
O11 Zn3 O2 117.29(8) 2 2_655 ?
O12 Zn3 O2 103.77(7) . 2_655 ?

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 C1 C2 C7 -171.4(2) . . . . ?
O2 C1 C2 C7 9.9(3) . . . . ?
O1 C1 C2 C3 10.7(3) . . . . ?
O2 C1 C2 C3 -168.0(2) . . . . ?
C7 C2 C3 C4 -2.1(3) . . . . ?
C1 C2 C3 C4 175.78(19) . . . . ?
C2 C3 C4 O3 -179.09(19) . . . . ?
C2 C3 C4 C5 1.0(3) . . . . ?
O3 C4 C5 O6 6.2(3) . . . . ?
C3 C4 C5 O6 -173.87(19) . . . . ?
O3 C4 C5 C6 -179.04(19) . . . . ?
C3 C4 C5 C6 0.9(3) . . . . ?
O6 C5 C6 O9 -4.6(3) . . . . ?
C4 C5 C6 O9 -178.93(19) . . . . ?
O6 C5 C6 C7 172.7(2) . . . . ?
C4 C5 C6 C7 -1.7(3) . . . . ?
C3 C2 C7 C6 1.4(3) . . . . ?
C1 C2 C7 C6 -176.5(2) . . . . ?
O9 C6 C7 C2 177.6(2) . . . . ?
C5 C6 C7 C2 0.6(3) . . . . ?
O3 C8 C9 O5 -9.6(3) . . . . ?
O3 C8 C9 O4 172.13(19) . . . . ?
O6 C10 C11 O8 173.4(2) . . . . ?
O6 C10 C11 O7 -7.3(3) . . . . ?
O9 C12 C13 O10 -8.5(3) . . . . ?
O9 C12 C13 O11 169.65(19) . . . . ?
O2 C1 O1 Zn2 -6.1(3) . . . 2_645 ?
C2 C1 O1 Zn2 175.30(14) . . . 2_645 ?
O1 C1 O2 Zn3 -36.8(3) . . . 2_645 ?
C2 C1 O2 Zn3 141.83(16) . . . 2_645 ?
C3 C4 O3 C8 7.7(3) . . . . ?
C5 C4 O3 C8 -172.37(19) . . . . ?
C3 C4 O3 Zn2 150.14(17) . . . . ?
C5 C4 O3 Zn2 -30.0(2) . . . . ?
C9 C8 O3 C4 161.81(18) . . . . ?
C9 C8 O3 Zn2 16.9(2) . . . . ?
O5 C9 O4 Zn3 -12.4(3) . . . 3_666 ?
C8 C9 O4 Zn3 165.77(15) . . . 3_666 ?
O4 C9 O5 Zn2 172.65(17) . . . . ?
C8 C9 O5 Zn2 -5.4(3) . . . . ?
C6 C5 O6 C10 64.9(3) . . . . ?
C4 C5 O6 C10 -120.6(2) . . . . ?
C6 C5 O6 Zn2 -156.07(16) . . . . ?
C4 C5 O6 Zn2 18.5(2) . . . . ?
C11 C10 O6 C5 142.7(2) . . . . ?
C11 C10 O6 Zn2 2.2(2) . . . . ?
O8 C11 O7 Zn2 -169.42(19) . . . . ?
C10 C11 O7 Zn2 11.3(3) . . . . ?
O8 C11 O7 Zn1 -18.8(3) . . . . ?
C10 C11 O7 Zn1 161.97(16) . . . . ?
C7 C6 O9 C12 9.8(3) . . . . ?
C5 C6 O9 C12 -173.09(19) . . . . ?
C13 C12 O9 C6 75.6(2) . . . . ?
O10 C13 O11 Zn3 3.5(3) . . . 2_545 ?
C12 C13 O11 Zn3 -174.60(15) . . . 2_545 ?
Zn3 O12 Zn1 O12 98.9(12) . . . 3_566 ?
Zn2 O12 Zn1 O12 -19.3(12) . . . 3_566 ?
Zn3 O12 Zn1 O7 103.48(12) . . . . ?
Zn2 O12 Zn1 O7 -14.68(6) . . . . ?
Zn3 O12 Zn1 O7 -76.52(12) . . . 3_566 ?
Zn2 O12 Zn1 O7 165.33(6) . . . 3_566 ?
Zn3 O12 Zn1 O13 12.42(12) . . . . ?
Zn2 O12 Zn1 O13 -105.73(7) . . . . ?
Zn3 O12 Zn1 O13 -167.58(12) . . . 3_566 ?
Zn2 O12 Zn1 O13 74.27(7) . . . 3_566 ?
Zn3 O12 Zn1 Zn2 118.15(14) . . . . ?
Zn3 O12 Zn1 Zn2 -61.85(14) . . . 3_566 ?
Zn2 O12 Zn1 Zn2 180.0 . . . 3_566 ?
C11 O7 Zn1 O12 37.71(18) . . . 3_566 ?
Zn2 O7 Zn1 O12 -164.45(7) . . . 3_566 ?
C11 O7 Zn1 O12 -142.29(18) . . . . ?
Zn2 O7 Zn1 O12 15.55(7) . . . . ?
C11 O7 Zn1 O7 25(9) . . . 3_566 ?
Zn2 O7 Zn1 O7 -177(9) . . . 3_566 ?
C11 O7 Zn1 O13 -50.87(18) . . . . ?
Zn2 O7 Zn1 O13 106.98(7) . . . . ?
C11 O7 Zn1 O13 129.13(18) . . . 3_566 ?
Zn2 O7 Zn1 O13 -73.02(7) . . . 3_566 ?
C11 O7 Zn1 Zn2 -157.8(2) . . . . ?
C11 O7 Zn1 Zn2 22.2(2) . . . 3_566 ?
Zn2 O7 Zn1 Zn2 180.0 . . . 3_566 ?
C11 O7 Zn2 O1 29.8(2) . . . 2_655 ?
Zn1 O7 Zn2 O1 -125.93(9) . . . 2_655 ?
C11 O7 Zn2 O5 -137.10(18) . . . . ?
Zn1 O7 Zn2 O5 67.12(8) . . . . ?
C11 O7 Zn2 O12 140.5(2) . . . . ?
Zn1 O7 Zn2 O12 -15.32(6) . . . . ?
C11 O7 Zn2 O3 -62.8(2) . . . . ?
Zn1 O7 Zn2 O3 141.42(6) . . . . ?
C11 O7 Zn2 O6 -7.36(18) . . . . ?
Zn1 O7 Zn2 O6 -163.14(8) . . . . ?
C11 O7 Zn2 Zn1 155.8(2) . . . . ?
C9 O5 Zn2 O1 -65.03(19) . . . 2_655 ?
C9 O5 Zn2 O7 106.26(18) . . . . ?
C9 O5 Zn2 O12 -175.78(19) . . . . ?
C9 O5 Zn2 O3 11.37(17) . . . . ?
C9 O5 Zn2 O6 21.0(2) . . . . ?
C9 O5 Zn2 Zn1 143.66(18) . . . . ?
Zn3 O12 Zn2 O1 13.43(9) . . . 2_655 ?
Zn1 O12 Zn2 O1 154.71(6) . . . 2_655 ?
Zn3 O12 Zn2 O7 -126.03(8) . . . . ?
Zn1 O12 Zn2 O7 15.25(6) . . . . ?
Zn3 O12 Zn2 O5 117.87(8) . . . . ?
Zn1 O12 Zn2 O5 -100.85(7) . . . . ?
Zn3 O12 Zn2 O3 135.40(12) . . . . ?
Zn1 O12 Zn2 O3 -83.32(15) . . . . ?
Zn3 O12 Zn2 O6 -79.75(9) . . . . ?
Zn1 O12 Zn2 O6 61.53(10) . . . . ?
Zn3 O12 Zn2 Zn1 -141.28(10) . . . . ?
C4 O3 Zn2 O1 -51.35(14) . . . 2_655 ?
C8 O3 Zn2 O1 92.76(15) . . . 2_655 ?
C4 O3 Zn2 O7 87.76(15) . . . . ?
C8 O3 Zn2 O7 -128.12(14) . . . . ?
C4 O3 Zn2 O5 -159.59(16) . . . . ?
C8 O3 Zn2 O5 -15.47(14) . . . . ?
C4 O3 Zn2 O12 -178.17(15) . . . . ?
C8 O3 Zn2 O12 -34.1(2) . . . . ?
C4 O3 Zn2 O6 28.20(13) . . . . ?
C8 O3 Zn2 O6 172.32(16) . . . . ?
C4 O3 Zn2 Zn1 120.89(13) . . . . ?
C8 O3 Zn2 Zn1 -95.00(14) . . . . ?
C5 O6 Zn2 O1 64.14(14) . . . 2_655 ?
C10 O6 Zn2 O1 -154.50(16) . . . 2_655 ?
C5 O6 Zn2 O7 -139.60(15) . . . . ?
C10 O6 Zn2 O7 1.75(15) . . . . ?
C5 O6 Zn2 O5 -33.77(17) . . . . ?
C10 O6 Zn2 O5 107.59(16) . . . . ?
C5 O6 Zn2 O12 170.95(13) . . . . ?
C10 O6 Zn2 O12 -47.69(18) . . . . ?
C5 O6 Zn2 O3 -23.58(13) . . . . ?
C10 O6 Zn2 O3 117.78(16) . . . . ?
C5 O6 Zn2 Zn1 -151.23(13) . . . . ?
C10 O6 Zn2 Zn1 -9.87(15) . . . . ?
O12 Zn1 Zn2 O1 135.19(11) 3_566 . . 2_655 ?
O12 Zn1 Zn2 O1 -44.80(11) . . . 2_655 ?
O7 Zn1 Zn2 O1 111.93(11) . . . 2_655 ?
O7 Zn1 Zn2 O1 -68.07(11) 3_566 . . 2_655 ?
O13 Zn1 Zn2 O1 34.43(10) . . . 2_655 ?
O13 Zn1 Zn2 O1 -145.57(10) 3_566 . . 2_655 ?
Zn2 Zn1 Zn2 O1 -101(5) 3_566 . . 2_655 ?
O12 Zn1 Zn2 O7 23.26(10) 3_566 . . . ?
O12 Zn1 Zn2 O7 -156.74(10) . . . . ?
O7 Zn1 Zn2 O7 180.0 3_566 . . . ?
O13 Zn1 Zn2 O7 -77.50(9) . . . . ?
O13 Zn1 Zn2 O7 102.50(9) 3_566 . . . ?
Zn2 Zn1 Zn2 O7 147(5) 3_566 . . . ?
O12 Zn1 Zn2 O5 -99.90(8) 3_566 . . . ?
O12 Zn1 Zn2 O5 80.10(8) . . . . ?
O7 Zn1 Zn2 O5 -123.16(9) . . . . ?
O7 Zn1 Zn2 O5 56.84(9) 3_566 . . . ?
O13 Zn1 Zn2 O5 159.34(7) . . . . ?
O13 Zn1 Zn2 O5 -20.66(7) 3_566 . . . ?
Zn2 Zn1 Zn2 O5 23(5) 3_566 . . . ?
O12 Zn1 Zn2 O12 180.0 3_566 . . . ?
O7 Zn1 Zn2 O12 156.74(10) . . . . ?
O7 Zn1 Zn2 O12 -23.26(10) 3_566 . . . ?
O13 Zn1 Zn2 O12 79.24(8) . . . . ?
O13 Zn1 Zn2 O12 -100.76(8) 3_566 . . . ?
Zn2 Zn1 Zn2 O12 -57(5) 3_566 . . . ?
O12 Zn1 Zn2 O3 -31.15(8) 3_566 . . . ?
O12 Zn1 Zn2 O3 148.86(8) . . . . ?
O7 Zn1 Zn2 O3 -54.41(9) . . . . ?
O7 Zn1 Zn2 O3 125.59(9) 3_566 . . . ?
O13 Zn1 Zn2 O3 -131.91(7) . . . . ?
O13 Zn1 Zn2 O3 48.09(7) 3_566 . . . ?
Zn2 Zn1 Zn2 O3 92(5) 3_566 . . . ?
O12 Zn1 Zn2 O6 39.98(8) 3_566 . . . ?
O12 Zn1 Zn2 O6 -140.02(8) . . . . ?
O7 Zn1 Zn2 O6 16.72(8) . . . . ?
O7 Zn1 Zn2 O6 -163.28(8) 3_566 . . . ?
O13 Zn1 Zn2 O6 -60.79(6) . . . . ?
O13 Zn1 Zn2 O6 119.21(6) 3_566 . . . ?
Zn2 Zn1 Zn2 O6 163(5) 3_566 . . . ?
Zn1 O12 Zn3 O4 92.81(12) . . . 3_666 ?
Zn2 O12 Zn3 O4 -151.38(7) . . . 3_666 ?
Zn1 O12 Zn3 O11 -18.74(15) . . . 2 ?
Zn2 O12 Zn3 O11 97.07(9) . . . 2 ?
Zn1 O12 Zn3 O2 -152.86(11) . . . 2_655 ?
Zn2 O12 Zn3 O2 -37.05(8) . . . 2_655 ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
O13 H1W O2 0.83 2.47 3.170(3) 142.7 2
O13 H1W O5 0.83 2.47 2.966(2) 119.4 3_566
O13 H2W O11 0.83 2.17 2.981(3) 167.4 4_576
O12 H12 O8 0.82 2.45 3.023(2) 127.6 3_566

_diffrn_measured_fraction_theta_max 0.998
_diffrn_reflns_theta_full        27.50
_diffrn_measured_fraction_theta_full 0.998
_refine_diff_density_max         0.923
_refine_diff_density_min         -0.543
_refine_diff_density_rms         0.075
####################################################################### 
# 
# 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 999330'
_audit_update_record             
;
2014-04-24 deposited with the CCDC.
2015-03-23 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 H22 Co3 O19'
_chemical_formula_weight         659.10

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'
Co Co 0.3494 0.9721 '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                   7.9468(3)
_cell_length_b                   12.5413(5)
_cell_length_c                   12.5620(5)
_cell_angle_alpha                111.67
_cell_angle_beta                 106.20
_cell_angle_gamma                94.38
_cell_volume                     1094.51(7)
_cell_formula_units_Z            2
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    6966
_cell_measurement_theta_min      2.72
_cell_measurement_theta_max      28.31

_exptl_crystal_description       block
_exptl_crystal_colour            purple
_exptl_crystal_size_max          0.27
_exptl_crystal_size_mid          0.21
_exptl_crystal_size_min          0.18
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    2.000
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             666
_exptl_absorpt_coefficient_mu    2.341
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.5706
_exptl_absorpt_correction_T_max  0.6780
_exptl_absorpt_process_details   sadabs

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      296(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            8426
_diffrn_reflns_av_R_equivalents  0.0107
_diffrn_reflns_av_sigmaI/netI    0.0148
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_theta_min         2.94
_diffrn_reflns_theta_max         25.49
_reflns_number_total             4045
_reflns_number_gt                3749
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'

_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)+(0.0379P)²+1.6898P] 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         4045
_refine_ls_number_parameters     318
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0303
_refine_ls_R_factor_gt           0.0277
_refine_ls_wR_factor_ref         0.0755
_refine_ls_wR_factor_gt          0.0737
_refine_ls_goodness_of_fit_ref   1.066
_refine_ls_restrained_S_all      1.066
_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
C1 C 0.7283(3) 0.5821(2) 0.8407(2) 0.0176(5) Uani 1 1 d . . .
C2 C 0.7489(3) 0.5129(2) 0.9179(2) 0.0170(5) Uani 1 1 d . . .
C3 C 0.7563(4) 0.3952(2) 0.8664(2) 0.0203(5) Uani 1 1 d . . .
H3 H 0.7492 0.3599 0.7854 0.024 Uiso 1 1 calc R . .
C4 C 0.7744(4) 0.3310(2) 0.9365(2) 0.0195(5) Uani 1 1 d . . .
C5 C 0.7861(3) 0.3848(2) 1.0581(2) 0.0174(5) Uani 1 1 d . . .
C6 C 0.7760(4) 0.5024(2) 1.1080(2) 0.0198(5) Uani 1 1 d . . .
C7 C 0.7592(4) 0.5675(2) 1.0386(2) 0.0205(5) Uani 1 1 d . . .
H7 H 0.7548 0.6465 1.0722 0.025 Uiso 1 1 calc R . .
C8 C 0.7305(5) 0.1485(2) 0.7683(2) 0.0344(7) Uani 1 1 d . . .
H8A H 0.8212 0.1693 0.7374 0.041 Uiso 1 1 calc R . .
H8B H 0.6186 0.1644 0.7275 0.041 Uiso 1 1 calc R . .
C9 C 0.7085(4) 0.0192(2) 0.7453(2) 0.0243(6) Uani 1 1 d . . .
C10 C 0.6428(4) 0.2685(3) 1.1287(3) 0.0392(8) Uani 1 1 d . . .
H10A H 0.5864 0.2019 1.0515 0.047 Uiso 1 1 calc R . .
H10B H 0.5638 0.3241 1.1366 0.047 Uiso 1 1 calc R . .
C11 C 0.6687(4) 0.2279(2) 1.2305(2) 0.0228(6) Uani 1 1 d . . .
C12 C 0.7230(4) 0.6506(2) 1.2741(2) 0.0252(6) Uani 1 1 d . . .
H12A H 0.6148 0.6501 1.2142 0.030 Uiso 1 1 calc R . .
H12B H 0.8127 0.7173 1.2919 0.030 Uiso 1 1 calc R . .
C13 C 0.6852(4) 0.6603(2) 1.3894(2) 0.0205(5) Uani 1 1 d . . .
Co1 Co 0.52977(5) 0.77129(3) 0.58161(3) 0.01968(10) Uani 1 1 d . . .
Co2 Co 0.75262(5) 0.83135(3) 0.84987(3) 0.01827(10) Uani 1 1 d . . .
Co3 Co 0.69604(4) 0.56406(3) 0.58493(3) 0.01653(10) Uani 1 1 d . . .
O1 O 0.7459(3) 0.69086(16) 0.89503(17) 0.0259(4) Uani 1 1 d . . .
O2 O 0.6924(3) 0.52526(16) 0.72917(16) 0.0296(5) Uani 1 1 d . . .
O3 O 0.7822(3) 0.21481(16) 0.89583(17) 0.0323(5) Uani 1 1 d . . .
O4 O 0.6183(3) -0.05086(16) 0.63878(17) 0.0324(5) Uani 1 1 d . . .
O5 O 0.7818(3) -0.00692(16) 0.83156(17) 0.0272(4) Uani 1 1 d . . .
O6 O 0.8092(2) 0.32221(15) 1.13026(16) 0.0199(4) Uani 1 1 d . . .
O7 O 0.8198(3) 0.2341(2) 1.2961(2) 0.0434(6) Uani 1 1 d . . .
O8 O 0.5250(2) 0.19084(16) 1.24290(16) 0.0228(4) Uani 1 1 d . . .
O9 O 0.7853(3) 0.54505(17) 1.22733(17) 0.0334(5) Uani 1 1 d . . .
O10 O 0.7324(3) 0.58898(16) 1.43295(16) 0.0246(4) Uani 1 1 d . . .
O11 O 0.6087(3) 0.74335(17) 1.43020(17) 0.0287(4) Uani 1 1 d . . .
O12 O 0.7689(2) 0.74420(14) 0.68214(15) 0.0190(4) Uani 1 1 d . . .
H12 H 0.8656 0.7694 0.6799 0.028 Uiso 1 1 d R . .
O13 O 0.5651(2) 0.39901(15) 0.45512(15) 0.0199(4) Uani 1 1 d . . .
H13 H 0.5962 0.3998 0.3988 0.030 Uiso 1 1 d R . .
O14 O 0.7343(3) 0.93174(19) 1.02064(19) 0.0415(6) Uani 1 1 d . . .
H1W H 0.7857 0.9996 1.0443 0.062 Uiso 1 1 d R . .
H2W H 0.7448 0.9117 1.0779 0.062 Uiso 1 1 d R . .
O15 O 1.0350(3) 0.86989(16) 0.92916(17) 0.0257(4) Uani 1 1 d . . .
H3W H 1.0630 0.8947 1.0046 0.039 Uiso 1 1 d R . .
H4W H 1.0743 0.8106 0.9027 0.039 Uiso 1 1 d R . .
O16 O 0.9536(3) 0.5256(3) 0.6056(2) 0.0542(7) Uani 1 1 d D . .
H5W H 0.9408 0.4626 0.5957 0.081 Uiso 1 1 d R . .
H6W H 1.0232 0.5512 0.6762 0.081 Uiso 1 1 d RD . .
O17 O 0.2580(3) 0.7835(3) 0.5011(2) 0.0529(7) Uani 1 1 d . . .
H7W H 0.1982 0.7763 0.5426 0.079 Uiso 1 1 d R . .
H8W H 0.2441 0.8407 0.4838 0.079 Uiso 1 1 d R . .
O18 O 0.8002(6) 0.9786(3) 0.4599(4) 0.0868(11) Uani 1 1 d . . .
H9W H 0.6894 0.9595 0.4344 0.09(2) Uiso 1 1 d R . .
H10W H 0.8435 0.9693 0.5234 0.45(11) Uiso 1 1 d R . .
O19 O 0.3054(19) 0.0680(8) 0.7800(7) 0.338(8) Uani 1 1 d . . .
H12W H 0.2494 0.0216 0.7089 0.507 Uiso 1 1 d R . .
H11W H 0.3964 0.0605 0.8011 0.507 Uiso 1 1 d R . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
C1 O2 1.249(3) . ?
C1 O1 1.255(3) . ?
C1 C2 1.510(3) . ?
C2 C3 1.388(3) . ?
C2 C7 1.389(3) . ?
C3 C4 1.384(4) . ?
C3 H3 0.9300 . ?
C4 O3 1.368(3) . ?
C4 C5 1.395(3) . ?
C5 O6 1.388(3) . ?
C5 C6 1.393(4) . ?
C6 O9 1.371(3) . ?
C6 C7 1.387(4) . ?
C7 H7 0.9300 . ?
C8 O3 1.422(3) . ?
C8 C9 1.525(4) . ?
C8 H8A 0.9700 . ?
C8 H8B 0.9700 . ?
C9 O5 1.249(3) . ?
C9 O4 1.255(3) . ?
C10 O6 1.429(3) . ?
C10 C11 1.512(4) . ?
C10 H10A 0.9700 . ?
C10 H10B 0.9700 . ?
C11 O7 1.230(4) . ?
C11 O8 1.272(3) . ?
C12 O9 1.425(3) . ?
C12 C13 1.523(3) . ?
C12 H12A 0.9700 . ?
C12 H12B 0.9700 . ?
C13 O10 1.241(3) . ?
C13 O11 1.262(3) . ?
Co1 O13 2.0432(17) 2_666 ?
Co1 O4 2.0691(19) 1_565 ?
Co1 O11 2.0833(19) 1_554 ?
Co1 O12 2.0972(18) . ?
Co1 O17 2.158(2) . ?
Co1 O8 2.2513(18) 2_667 ?
Co2 O12 2.0308(17) . ?
Co2 O1 2.0419(18) . ?
Co2 O14 2.102(2) . ?
Co2 O15 2.1197(19) . ?
Co2 O5 2.1268(19) 1_565 ?
Co2 O8 2.1294(19) 2_667 ?
Co3 O2 2.0491(18) . ?
Co3 O13 2.0636(17) . ?
Co3 O12 2.0734(17) . ?
Co3 O16 2.107(2) . ?
Co3 O13 2.1237(18) 2_666 ?
Co3 O10 2.1356(18) 1_554 ?
O4 Co1 2.0691(19) 1_545 ?
O5 Co2 2.1267(18) 1_545 ?
O8 Co2 2.1294(19) 2_667 ?
O8 Co1 2.2513(18) 2_667 ?
O10 Co3 2.1356(18) 1_556 ?
O11 Co1 2.0833(19) 1_556 ?
O12 H12 0.8202 . ?
O13 Co1 2.0432(17) 2_666 ?
O13 Co3 2.1237(18) 2_666 ?
O13 H13 0.8153 . ?
O14 H1W 0.8200 . ?
O14 H2W 0.8302 . ?
O15 H3W 0.8360 . ?
O15 H4W 0.8200 . ?
O16 H5W 0.7470 . ?
O16 H6W 0.8278 . ?
O17 H7W 0.8200 . ?
O17 H8W 0.8293 . ?
O18 H9W 0.8301 . ?
O18 H10W 0.8304 . ?
O19 H12W 0.8301 . ?
O19 H11W 0.7232 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
O2 C1 O1 126.7(2) . . ?
O2 C1 C2 116.7(2) . . ?
O1 C1 C2 116.5(2) . . ?
C3 C2 C7 121.3(2) . . ?
C3 C2 C1 119.1(2) . . ?
C7 C2 C1 119.6(2) . . ?
C4 C3 C2 119.4(2) . . ?
C4 C3 H3 120.3 . . ?
C2 C3 H3 120.3 . . ?
O3 C4 C3 124.8(2) . . ?
O3 C4 C5 115.2(2) . . ?
C3 C4 C5 120.0(2) . . ?
O6 C5 C6 119.5(2) . . ?
O6 C5 C4 120.6(2) . . ?
C6 C5 C4 119.9(2) . . ?
O9 C6 C7 124.8(2) . . ?
O9 C6 C5 114.7(2) . . ?
C7 C6 C5 120.4(2) . . ?
C6 C7 C2 118.9(2) . . ?
C6 C7 H7 120.5 . . ?
C2 C7 H7 120.5 . . ?
O3 C8 C9 107.8(2) . . ?
O3 C8 H8A 110.1 . . ?
C9 C8 H8A 110.1 . . ?
O3 C8 H8B 110.1 . . ?
C9 C8 H8B 110.1 . . ?
H8A C8 H8B 108.5 . . ?
O5 C9 O4 126.6(2) . . ?
O5 C9 C8 118.1(2) . . ?
O4 C9 C8 115.3(2) . . ?
O6 C10 C11 111.5(2) . . ?
O6 C10 H10A 109.3 . . ?
C11 C10 H10A 109.3 . . ?
O6 C10 H10B 109.3 . . ?
C11 C10 H10B 109.3 . . ?
H10A C10 H10B 108.0 . . ?
O7 C11 O8 124.3(2) . . ?
O7 C11 C10 120.7(3) . . ?
O8 C11 C10 114.9(2) . . ?
O9 C12 C13 109.2(2) . . ?
O9 C12 H12A 109.8 . . ?
C13 C12 H12A 109.8 . . ?
O9 C12 H12B 109.8 . . ?
C13 C12 H12B 109.8 . . ?
H12A C12 H12B 108.3 . . ?
O10 C13 O11 127.4(2) . . ?
O10 C13 C12 118.2(2) . . ?
O11 C13 C12 114.3(2) . . ?
O13 Co1 O4 172.79(7) 2_666 1_565 ?
O13 Co1 O11 98.69(7) 2_666 1_554 ?
O4 Co1 O11 88.51(8) 1_565 1_554 ?
O13 Co1 O12 83.99(7) 2_666 . ?
O4 Co1 O12 95.26(8) 1_565 . ?
O11 Co1 O12 94.09(7) 1_554 . ?
O13 Co1 O17 87.89(10) 2_666 . ?
O4 Co1 O17 91.55(10) 1_565 . ?
O11 Co1 O17 96.93(9) 1_554 . ?
O12 Co1 O17 167.18(9) . . ?
O13 Co1 O8 84.01(7) 2_666 2_667 ?
O4 Co1 O8 88.79(7) 1_565 2_667 ?
O11 Co1 O8 173.98(8) 1_554 2_667 ?
O12 Co1 O8 80.80(7) . 2_667 ?
O17 Co1 O8 88.52(9) . 2_667 ?
O12 Co2 O1 96.33(7) . . ?
O12 Co2 O14 176.04(8) . . ?
O1 Co2 O14 87.61(8) . . ?
O12 Co2 O15 91.23(7) . . ?
O1 Co2 O15 88.63(8) . . ?
O14 Co2 O15 89.24(9) . . ?
O12 Co2 O5 90.98(7) . 1_565 ?
O1 Co2 O5 171.21(8) . 1_565 ?
O14 Co2 O5 85.13(8) . 1_565 ?
O15 Co2 O5 86.32(8) . 1_565 ?
O12 Co2 O8 85.34(7) . 2_667 ?
O1 Co2 O8 99.51(8) . 2_667 ?
O14 Co2 O8 93.65(9) . 2_667 ?
O15 Co2 O8 171.46(7) . 2_667 ?
O5 Co2 O8 85.92(7) 1_565 2_667 ?
O2 Co3 O13 94.83(7) . . ?
O2 Co3 O12 96.11(7) . . ?
O13 Co3 O12 162.82(7) . . ?
O2 Co3 O16 89.25(9) . . ?
O13 Co3 O16 94.68(10) . . ?
O12 Co3 O16 98.66(10) . . ?
O2 Co3 O13 96.70(8) . 2_666 ?
O13 Co3 O13 83.00(7) . 2_666 ?
O12 Co3 O13 82.60(7) . 2_666 ?
O16 Co3 O13 173.76(8) . 2_666 ?
O2 Co3 O10 170.99(8) . 1_554 ?
O13 Co3 O10 82.93(7) . 1_554 ?
O12 Co3 O10 88.19(7) . 1_554 ?
O16 Co3 O10 82.25(9) . 1_554 ?
O13 Co3 O10 91.70(7) 2_666 1_554 ?
C1 O1 Co2 136.25(17) . . ?
C1 O2 Co3 135.83(17) . . ?
C4 O3 C8 118.0(2) . . ?
C9 O4 Co1 125.66(17) . 1_545 ?
C9 O5 Co2 130.78(18) . 1_545 ?
C5 O6 C10 112.4(2) . . ?
C11 O8 Co2 134.73(17) . 2_667 ?
C11 O8 Co1 126.88(17) . 2_667 ?
Co2 O8 Co1 90.29(7) 2_667 2_667 ?
C6 O9 C12 117.8(2) . . ?
C13 O10 Co3 131.18(17) . 1_556 ?
C13 O11 Co1 122.25(17) . 1_556 ?
Co2 O12 Co3 124.66(9) . . ?
Co2 O12 Co1 97.62(7) . . ?
Co3 O12 Co1 92.50(7) . . ?
Co2 O12 H12 109.7 . . ?
Co3 O12 H12 110.7 . . ?
Co1 O12 H12 121.0 . . ?
Co1 O13 Co3 147.43(9) 2_666 . ?
Co1 O13 Co3 92.58(7) 2_666 2_666 ?
Co3 O13 Co3 97.00(7) . 2_666 ?
Co1 O13 H13 108.0 2_666 . ?
Co3 O13 H13 99.9 . . ?
Co3 O13 H13 103.8 2_666 . ?
Co2 O14 H1W 109.5 . . ?
Co2 O14 H2W 126.9 . . ?
H1W O14 H2W 111.6 . . ?
Co2 O15 H3W 109.6 . . ?
Co2 O15 H4W 109.5 . . ?
H3W O15 H4W 110.1 . . ?
Co3 O16 H5W 104.4 . . ?
Co3 O16 H6W 115.7 . . ?
H5W O16 H6W 96.1 . . ?
Co1 O17 H7W 109.6 . . ?
Co1 O17 H8W 116.8 . . ?
H7W O17 H8W 112.3 . . ?
H9W O18 H10W 111.1 . . ?
H12W O19 H11W 113.2 . . ?

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
O2 C1 C2 C3 10.4(4) . . . . ?
O1 C1 C2 C3 -170.9(2) . . . . ?
O2 C1 C2 C7 -169.3(2) . . . . ?
O1 C1 C2 C7 9.4(4) . . . . ?
C7 C2 C3 C4 0.0(4) . . . . ?
C1 C2 C3 C4 -179.7(2) . . . . ?
C2 C3 C4 O3 179.6(3) . . . . ?
C2 C3 C4 C5 -0.4(4) . . . . ?
O3 C4 C5 O6 1.8(4) . . . . ?
C3 C4 C5 O6 -178.2(2) . . . . ?
O3 C4 C5 C6 -178.7(2) . . . . ?
C3 C4 C5 C6 1.3(4) . . . . ?
O6 C5 C6 O9 -1.8(4) . . . . ?
C4 C5 C6 O9 178.7(2) . . . . ?
O6 C5 C6 C7 177.8(2) . . . . ?
C4 C5 C6 C7 -1.7(4) . . . . ?
O9 C6 C7 C2 -179.2(3) . . . . ?
C5 C6 C7 C2 1.3(4) . . . . ?
C3 C2 C7 C6 -0.4(4) . . . . ?
C1 C2 C7 C6 179.3(2) . . . . ?
O3 C8 C9 O5 -19.3(4) . . . . ?
O3 C8 C9 O4 161.5(3) . . . . ?
O6 C10 C11 O7 -5.9(4) . . . . ?
O6 C10 C11 O8 172.7(2) . . . . ?
O9 C12 C13 O10 8.8(4) . . . . ?
O9 C12 C13 O11 -171.8(2) . . . . ?
O2 C1 O1 Co2 -6.8(4) . . . . ?
C2 C1 O1 Co2 174.63(18) . . . . ?
O12 Co2 O1 C1 -10.5(3) . . . . ?
O14 Co2 O1 C1 169.1(3) . . . . ?
O15 Co2 O1 C1 -101.6(3) . . . . ?
O5 Co2 O1 C1 -156.5(5) 1_565 . . . ?
O8 Co2 O1 C1 75.8(3) 2_667 . . . ?
O1 C1 O2 Co3 16.0(5) . . . . ?
C2 C1 O2 Co3 -165.41(19) . . . . ?
O13 Co3 O2 C1 -170.3(3) . . . . ?
O12 Co3 O2 C1 -3.6(3) . . . . ?
O16 Co3 O2 C1 95.1(3) . . . . ?
O13 Co3 O2 C1 -86.8(3) 2_666 . . . ?
O10 Co3 O2 C1 114.5(5) 1_554 . . . ?
C3 C4 O3 C8 -14.2(4) . . . . ?
C5 C4 O3 C8 165.8(3) . . . . ?
C9 C8 O3 C4 -166.9(3) . . . . ?
O5 C9 O4 Co1 10.6(4) . . . 1_545 ?
C8 C9 O4 Co1 -170.3(2) . . . 1_545 ?
O4 C9 O5 Co2 -12.4(5) . . . 1_545 ?
C8 C9 O5 Co2 168.5(2) . . . 1_545 ?
C6 C5 O6 C10 89.4(3) . . . . ?
C4 C5 O6 C10 -91.0(3) . . . . ?
C11 C10 O6 C5 -165.3(2) . . . . ?
O7 C11 O8 Co2 179.8(2) . . . 2_667 ?
C10 C11 O8 Co2 1.3(4) . . . 2_667 ?
O7 C11 O8 Co1 41.0(4) . . . 2_667 ?
C10 C11 O8 Co1 -137.5(2) . . . 2_667 ?
C7 C6 O9 C12 19.1(4) . . . . ?
C5 C6 O9 C12 -161.4(2) . . . . ?
C13 C12 O9 C6 160.9(2) . . . . ?
O11 C13 O10 Co3 4.2(4) . . . 1_556 ?
C12 C13 O10 Co3 -176.47(18) . . . 1_556 ?
O10 C13 O11 Co1 -3.9(4) . . . 1_556 ?
C12 C13 O11 Co1 176.79(18) . . . 1_556 ?
O1 Co2 O12 Co3 20.15(12) . . . . ?
O14 Co2 O12 Co3 -154.3(12) . . . . ?
O15 Co2 O12 Co3 108.91(11) . . . . ?
O5 Co2 O12 Co3 -164.75(11) 1_565 . . . ?
O8 Co2 O12 Co3 -78.93(11) 2_667 . . . ?
O1 Co2 O12 Co1 118.54(8) . . . . ?
O14 Co2 O12 Co1 -55.9(13) . . . . ?
O15 Co2 O12 Co1 -152.70(7) . . . . ?
O5 Co2 O12 Co1 -66.36(8) 1_565 . . . ?
O8 Co2 O12 Co1 19.46(7) 2_667 . . . ?
O2 Co3 O12 Co2 -16.17(12) . . . . ?
O13 Co3 O12 Co2 113.1(2) . . . . ?
O16 Co3 O12 Co2 -106.34(12) . . . . ?
O13 Co3 O12 Co2 79.83(11) 2_666 . . . ?
O10 Co3 O12 Co2 171.78(11) 1_554 . . . ?
O2 Co3 O12 Co1 -117.21(8) . . . . ?
O13 Co3 O12 Co1 12.1(3) . . . . ?
O16 Co3 O12 Co1 152.62(8) . . . . ?
O13 Co3 O12 Co1 -21.21(7) 2_666 . . . ?
O10 Co3 O12 Co1 70.74(7) 1_554 . . . ?
O13 Co1 O12 Co2 -103.44(7) 2_666 . . . ?
O4 Co1 O12 Co2 69.36(8) 1_565 . . . ?
O11 Co1 O12 Co2 158.24(8) 1_554 . . . ?
O17 Co1 O12 Co2 -52.5(4) . . . . ?
O8 Co1 O12 Co2 -18.55(7) 2_667 . . . ?
O13 Co1 O12 Co3 22.02(7) 2_666 . . . ?
O4 Co1 O12 Co3 -165.18(7) 1_565 . . . ?
O11 Co1 O12 Co3 -76.31(7) 1_554 . . . ?
O17 Co1 O12 Co3 73.0(4) . . . . ?
O8 Co1 O12 Co3 106.90(7) 2_667 . . . ?
O2 Co3 O13 Co1 -9.87(19) . . . 2_666 ?
O12 Co3 O13 Co1 -139.3(2) . . . 2_666 ?
O16 Co3 O13 Co1 79.77(19) . . . 2_666 ?
O13 Co3 O13 Co1 -106.05(19) 2_666 . . 2_666 ?
O10 Co3 O13 Co1 161.35(18) 1_554 . . 2_666 ?
O2 Co3 O13 Co3 96.18(8) . . . 2_666 ?
O12 Co3 O13 Co3 -33.2(3) . . . 2_666 ?
O16 Co3 O13 Co3 -174.18(9) . . . 2_666 ?
O13 Co3 O13 Co3 0.0 2_666 . . 2_666 ?
O10 Co3 O13 Co3 -92.60(8) 1_554 . . 2_666 ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
O19 H12W O18 0.83 2.04 2.709(9) 136.7 2_666
O18 H10W O4 0.83 2.65 3.102(4) 115.8 1_565
O17 H8W O18 0.83 2.20 2.935(4) 147.9 2_676
O17 H7W O7 0.82 2.12 2.863(3) 150.4 2_667
O16 H6W O9 0.83 2.36 2.953(3) 129.0 2_767
O16 H6W O6 0.83 2.29 3.081(3) 161.2 2_767
O15 H4W O6 0.82 1.93 2.746(2) 169.9 2_767
O15 H3W O3 0.84 2.37 2.872(3) 118.9 2_767
O15 H3W O5 0.84 1.98 2.733(3) 149.6 2_767
O14 H2W O19 0.83 1.87 2.609(6) 147.9 2_667
O14 H1W O15 0.82 1.95 2.729(3) 158.9 2_777
O13 H13 O10 0.82 2.36 2.781(3) 112.7 1_554
O12 H12 O7 0.82 2.44 3.184(3) 151.7 2_767

_diffrn_measured_fraction_theta_max 0.992
_diffrn_reflns_theta_full        25.49
_diffrn_measured_fraction_theta_full 0.992
_refine_diff_density_max         1.447
_refine_diff_density_min         -1.045
_refine_diff_density_rms         0.075

