# 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_pnna
_database_code_depnum_ccdc_archive 'CCDC 1057602'
_audit_update_record             
;
2015-04-02 deposited with the CCDC.
2015-10-08 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C14 H9 Cd N O7'
_chemical_formula_weight         415.62

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'
Cd Cd -0.8075 1.2024 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_symmetry_cell_setting           Orthorhombic
_symmetry_space_group_name_H-M   Pnna

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

_cell_length_a                   14.481(4)
_cell_length_b                   25.238(7)
_cell_length_c                   7.5208(19)
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_volume                     2748.5(12)
_cell_formula_units_Z            8
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    ?
_cell_measurement_theta_min      ?
_cell_measurement_theta_max      ?

_exptl_crystal_description       block
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.25
_exptl_crystal_size_mid          0.22
_exptl_crystal_size_min          0.20
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    2.009
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1632
_exptl_absorpt_coefficient_mu    1.628
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.6863
_exptl_absorpt_correction_T_max  0.7366
_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  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            18100
_diffrn_reflns_av_R_equivalents  0.0210
_diffrn_reflns_av_sigmaI/netI    0.0130
_diffrn_reflns_limit_h_min       -17
_diffrn_reflns_limit_h_max       17
_diffrn_reflns_limit_k_min       -26
_diffrn_reflns_limit_k_max       29
_diffrn_reflns_limit_l_min       -8
_diffrn_reflns_limit_l_max       8
_diffrn_reflns_theta_min         1.61
_diffrn_reflns_theta_max         25.05
_reflns_number_total             2427
_reflns_number_gt                2102
_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)+(0.0347P)²+3.5598P] 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         2427
_refine_ls_number_parameters     210
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0279
_refine_ls_R_factor_gt           0.0234
_refine_ls_wR_factor_ref         0.0678
_refine_ls_wR_factor_gt          0.0633
_refine_ls_goodness_of_fit_ref   1.044
_refine_ls_restrained_S_all      1.044
_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
Cd1 Cd 1.148588(16) 0.2500 1.2500 0.01971(10) Uani 1 2 d S . .
Cd2 Cd 1.053760(19) 0.2500 0.7500 0.02080(10) Uani 1 2 d S . .
O1 O 1.02894(13) 0.30549(7) 1.1808(3) 0.0326(4) Uani 1 1 d . . .
O2 O 1.00298(14) 0.32104(7) 0.8935(2) 0.0352(5) Uani 1 1 d . . .
O3 O 0.93057(18) 0.56991(9) 1.3587(3) 0.0544(7) Uani 1 1 d . . .
O4 O 0.83434(15) 0.57152(8) 1.1302(3) 0.0396(5) Uani 1 1 d . . .
H4 H 0.8252 0.6018 1.1657 0.059 Uiso 1 1 calc R . .
O5 O 0.65993(12) 0.27412(7) 0.4591(2) 0.0288(4) Uani 1 1 d . . .
O6 O 0.70760(14) 0.33448(8) 0.2668(2) 0.0300(5) Uani 1 1 d . . .
O7 O 0.96097(18) 0.19887(12) 0.9559(3) 0.0704(9) Uani 1 1 d . . .
H1W H 0.9797 0.1937 1.0575 0.085 Uiso 1 1 d R . .
H2W H 0.9719 0.2316 0.9392 0.085 Uiso 1 1 d R . .
N1 N 0.74891(15) 0.32161(8) 0.7297(3) 0.0211(5) Uani 1 1 d . . .
C1 C 1.00044(17) 0.33320(10) 1.0535(3) 0.0236(6) Uani 1 1 d . . .
C2 C 0.96384(17) 0.38778(10) 1.0978(3) 0.0223(5) Uani 1 1 d . . .
C3 C 1.00616(19) 0.41410(11) 1.2382(3) 0.0264(6) Uani 1 1 d . . .
H3 H 1.0502 0.3965 1.3060 0.032 Uiso 1 1 calc R . .
C4 C 0.98410(19) 0.46574(11) 1.2786(3) 0.0268(6) Uani 1 1 d . . .
H4A H 1.0136 0.4827 1.3726 0.032 Uiso 1 1 calc R . .
C5 C 0.91823(18) 0.49265(10) 1.1802(3) 0.0243(5) Uani 1 1 d . . .
C6 C 0.8954(2) 0.54825(11) 1.2332(3) 0.0289(6) Uani 1 1 d . . .
C7 C 0.87544(18) 0.46670(10) 1.0402(3) 0.0238(5) Uani 1 1 d . . .
H7 H 0.8312 0.4846 0.9737 0.029 Uiso 1 1 calc R . .
C8 C 0.89681(16) 0.41471(10) 0.9966(3) 0.0216(6) Uani 1 1 d . . .
C9 C 0.84652(16) 0.39020(10) 0.8448(4) 0.0221(6) Uani 1 1 d . . .
C10 C 0.84500(18) 0.41485(11) 0.6797(4) 0.0291(6) Uani 1 1 d . . .
H10 H 0.8754 0.4469 0.6630 0.035 Uiso 1 1 calc R . .
C11 C 0.79799(18) 0.39145(10) 0.5400(4) 0.0273(6) Uani 1 1 d . . .
H11 H 0.7975 0.4072 0.4282 0.033 Uiso 1 1 calc R . .
C12 C 0.75211(17) 0.34467(9) 0.5686(3) 0.0206(5) Uani 1 1 d . . .
C13 C 0.70318(17) 0.31634(9) 0.4190(3) 0.0207(5) Uani 1 1 d . . .
C14 C 0.79584(17) 0.34373(10) 0.8632(3) 0.0231(5) Uani 1 1 d . . .
H14 H 0.7946 0.3273 0.9738 0.028 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
Cd1 O5 2.2768(19) 6_657 ?
Cd1 O5 2.2768(19) 7_666 ?
Cd1 O1 2.2878(19) 4_557 ?
Cd1 O1 2.2878(19) . ?
Cd1 N1 2.324(2) 6_657 ?
Cd1 N1 2.324(2) 7_666 ?
Cd2 O2 2.2183(18) . ?
Cd2 O2 2.2183(18) 4_556 ?
Cd2 O5 2.2820(18) 7_666 ?
Cd2 O5 2.2820(18) 6_656 ?
Cd2 O7 2.423(2) . ?
Cd2 O7 2.423(2) 4_556 ?
Cd2 H2W 1.9100 . ?
O1 C1 1.255(3) . ?
O2 C1 1.242(3) . ?
O3 C6 1.204(3) . ?
O4 C6 1.314(3) . ?
O4 H4 0.8200 . ?
O5 C13 1.272(3) . ?
O5 Cd1 2.2768(19) 6_557 ?
O5 Cd2 2.2820(18) 6_556 ?
O6 C13 1.235(3) . ?
O7 H1W 0.8207 . ?
O7 H2W 0.8499 . ?
N1 C14 1.335(3) . ?
N1 C12 1.345(3) . ?
N1 Cd1 2.324(2) 6_557 ?
C1 C2 1.513(3) . ?
C2 C3 1.390(4) . ?
C2 C8 1.408(3) . ?
C3 C4 1.376(4) . ?
C3 H3 0.9300 . ?
C4 C5 1.385(4) . ?
C4 H4A 0.9300 . ?
C5 C7 1.386(4) . ?
C5 C6 1.495(4) . ?
C7 C8 1.387(4) . ?
C7 H7 0.9300 . ?
C8 C9 1.489(3) . ?
C9 C10 1.389(4) . ?
C9 C14 1.390(4) . ?
C10 C11 1.384(4) . ?
C10 H10 0.9300 . ?
C11 C12 1.372(4) . ?
C11 H11 0.9300 . ?
C12 C13 1.510(3) . ?
C14 H14 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
O5 Cd1 O5 171.73(9) 6_657 7_666 ?
O5 Cd1 O1 89.98(7) 6_657 4_557 ?
O5 Cd1 O1 96.29(7) 7_666 4_557 ?
O5 Cd1 O1 96.29(7) 6_657 . ?
O5 Cd1 O1 89.98(7) 7_666 . ?
O1 Cd1 O1 81.55(10) 4_557 . ?
O5 Cd1 N1 71.57(6) 6_657 6_657 ?
O5 Cd1 N1 103.06(7) 7_666 6_657 ?
O1 Cd1 N1 159.16(7) 4_557 6_657 ?
O1 Cd1 N1 90.70(8) . 6_657 ?
O5 Cd1 N1 103.06(7) 6_657 7_666 ?
O5 Cd1 N1 71.57(6) 7_666 7_666 ?
O1 Cd1 N1 90.70(8) 4_557 7_666 ?
O1 Cd1 N1 159.16(7) . 7_666 ?
N1 Cd1 N1 102.62(11) 6_657 7_666 ?
O2 Cd2 O2 141.28(11) . 4_556 ?
O2 Cd2 O5 95.95(7) . 7_666 ?
O2 Cd2 O5 110.06(7) 4_556 7_666 ?
O2 Cd2 O5 110.06(7) . 6_656 ?
O2 Cd2 O5 95.95(7) 4_556 6_656 ?
O5 Cd2 O5 95.29(10) 7_666 6_656 ?
O2 Cd2 O7 86.31(9) . . ?
O2 Cd2 O7 72.35(8) 4_556 . ?
O5 Cd2 O7 77.93(8) 7_666 . ?
O5 Cd2 O7 163.01(9) 6_656 . ?
O2 Cd2 O7 72.35(8) . 4_556 ?
O2 Cd2 O7 86.31(9) 4_556 4_556 ?
O5 Cd2 O7 163.00(9) 7_666 4_556 ?
O5 Cd2 O7 77.93(8) 6_656 4_556 ?
O7 Cd2 O7 112.63(14) . 4_556 ?
O2 Cd2 H2W 68.2 . . ?
O2 Cd2 H2W 87.7 4_556 . ?
O5 Cd2 H2W 80.8 7_666 . ?
O5 Cd2 H2W 175.4 6_656 . ?
O7 Cd2 H2W 18.1 . . ?
O7 Cd2 H2W 105.2 4_556 . ?
C1 O1 Cd1 139.78(18) . . ?
C1 O2 Cd2 132.91(17) . . ?
C6 O4 H4 109.5 . . ?
C13 O5 Cd1 119.16(15) . 6_557 ?
C13 O5 Cd2 113.06(15) . 6_556 ?
Cd1 O5 Cd2 122.84(8) 6_557 6_556 ?
Cd2 O7 H1W 119.8 . . ?
Cd2 O7 H2W 44.4 . . ?
H1W O7 H2W 103.3 . . ?
C14 N1 C12 118.6(2) . . ?
C14 N1 Cd1 126.47(16) . 6_557 ?
C12 N1 Cd1 114.66(16) . 6_557 ?
O2 C1 O1 126.3(2) . . ?
O2 C1 C2 116.7(2) . . ?
O1 C1 C2 117.0(2) . . ?
C3 C2 C8 118.9(2) . . ?
C3 C2 C1 116.6(2) . . ?
C8 C2 C1 124.2(2) . . ?
C4 C3 C2 121.2(2) . . ?
C4 C3 H3 119.4 . . ?
C2 C3 H3 119.4 . . ?
C3 C4 C5 120.4(2) . . ?
C3 C4 H4A 119.8 . . ?
C5 C4 H4A 119.8 . . ?
C4 C5 C7 118.8(2) . . ?
C4 C5 C6 118.0(2) . . ?
C7 C5 C6 123.2(2) . . ?
O3 C6 O4 122.9(3) . . ?
O3 C6 C5 122.8(3) . . ?
O4 C6 C5 114.3(2) . . ?
C5 C7 C8 121.8(2) . . ?
C5 C7 H7 119.1 . . ?
C8 C7 H7 119.1 . . ?
C7 C8 C2 118.8(2) . . ?
C7 C8 C9 117.7(2) . . ?
C2 C8 C9 123.4(2) . . ?
C10 C9 C14 117.3(2) . . ?
C10 C9 C8 120.5(2) . . ?
C14 C9 C8 122.2(2) . . ?
C11 C10 C9 119.7(2) . . ?
C11 C10 H10 120.2 . . ?
C9 C10 H10 120.2 . . ?
C12 C11 C10 119.1(3) . . ?
C12 C11 H11 120.4 . . ?
C10 C11 H11 120.4 . . ?
N1 C12 C11 122.0(2) . . ?
N1 C12 C13 116.8(2) . . ?
C11 C12 C13 121.2(2) . . ?
O6 C13 O5 123.8(2) . . ?
O6 C13 C12 119.4(2) . . ?
O5 C13 C12 116.8(2) . . ?
N1 C14 C9 123.1(2) . . ?
N1 C14 H14 118.4 . . ?
C9 C14 H14 118.4 . . ?

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
O5 Cd1 O1 C1 144.7(3) 6_657 . . . ?
O5 Cd1 O1 C1 -29.9(3) 7_666 . . . ?
O1 Cd1 O1 C1 -126.3(3) 4_557 . . . ?
N1 Cd1 O1 C1 73.2(3) 6_657 . . . ?
N1 Cd1 O1 C1 -57.1(4) 7_666 . . . ?
O2 Cd2 O2 C1 106.5(3) 4_556 . . . ?
O5 Cd2 O2 C1 -26.5(3) 7_666 . . . ?
O5 Cd2 O2 C1 -124.3(2) 6_656 . . . ?
O7 Cd2 O2 C1 51.0(3) . . . . ?
O7 Cd2 O2 C1 166.1(3) 4_556 . . . ?
Cd2 O2 C1 O1 0.3(4) . . . . ?
Cd2 O2 C1 C2 177.00(17) . . . . ?
Cd1 O1 C1 O2 39.0(4) . . . . ?
Cd1 O1 C1 C2 -137.7(2) . . . . ?
O2 C1 C2 C3 -143.2(3) . . . . ?
O1 C1 C2 C3 33.8(3) . . . . ?
O2 C1 C2 C8 30.7(4) . . . . ?
O1 C1 C2 C8 -152.3(2) . . . . ?
C8 C2 C3 C4 -0.4(4) . . . . ?
C1 C2 C3 C4 173.8(2) . . . . ?
C2 C3 C4 C5 0.5(4) . . . . ?
C3 C4 C5 C7 -0.3(4) . . . . ?
C3 C4 C5 C6 178.5(3) . . . . ?
C4 C5 C6 O3 -1.4(4) . . . . ?
C7 C5 C6 O3 177.4(3) . . . . ?
C4 C5 C6 O4 178.1(3) . . . . ?
C7 C5 C6 O4 -3.1(4) . . . . ?
C4 C5 C7 C8 0.1(4) . . . . ?
C6 C5 C7 C8 -178.7(2) . . . . ?
C5 C7 C8 C2 0.0(4) . . . . ?
C5 C7 C8 C9 179.5(2) . . . . ?
C3 C2 C8 C7 0.2(4) . . . . ?
C1 C2 C8 C7 -173.6(2) . . . . ?
C3 C2 C8 C9 -179.4(2) . . . . ?
C1 C2 C8 C9 6.9(4) . . . . ?
C7 C8 C9 C10 53.7(3) . . . . ?
C2 C8 C9 C10 -126.8(3) . . . . ?
C7 C8 C9 C14 -123.1(3) . . . . ?
C2 C8 C9 C14 56.5(3) . . . . ?
C14 C9 C10 C11 -3.2(4) . . . . ?
C8 C9 C10 C11 179.9(2) . . . . ?
C9 C10 C11 C12 1.3(4) . . . . ?
C14 N1 C12 C11 -3.4(4) . . . . ?
Cd1 N1 C12 C11 171.1(2) 6_557 . . . ?
C14 N1 C12 C13 176.1(2) . . . . ?
Cd1 N1 C12 C13 -9.3(3) 6_557 . . . ?
C10 C11 C12 N1 2.1(4) . . . . ?
C10 C11 C12 C13 -177.4(2) . . . . ?
Cd1 O5 C13 O6 -174.89(19) 6_557 . . . ?
Cd2 O5 C13 O6 -19.0(3) 6_556 . . . ?
Cd1 O5 C13 C12 5.8(3) 6_557 . . . ?
Cd2 O5 C13 C12 161.66(16) 6_556 . . . ?
N1 C12 C13 O6 -176.6(2) . . . . ?
C11 C12 C13 O6 2.9(4) . . . . ?
N1 C12 C13 O5 2.7(3) . . . . ?
C11 C12 C13 O5 -177.8(2) . . . . ?
C12 N1 C14 C9 1.4(4) . . . . ?
Cd1 N1 C14 C9 -172.48(18) 6_557 . . . ?
C10 C9 C14 N1 1.9(4) . . . . ?
C8 C9 C14 N1 178.8(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
O7 H2W O2 0.85 2.33 3.178(3) 179.5 .
O7 H1W O1 0.82 2.09 2.906(3) 170.3 4_557
O4 H4 O6 0.82 1.84 2.655(3) 171.8 2_666

_diffrn_measured_fraction_theta_max 0.999
_diffrn_reflns_theta_full        25.05
_diffrn_measured_fraction_theta_full 0.999
_refine_diff_density_max         0.431
_refine_diff_density_min         -0.857
_refine_diff_density_rms         0.099
####################################################################### 
# 
# 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_p-1
_database_code_depnum_ccdc_archive 'CCDC 1057603'
_audit_update_record             
;
2015-04-02 deposited with the CCDC.
2015-10-08 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 H20 Mn1.50 N3 O9'
_chemical_formula_weight         600.86

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           Triclinic
_symmetry_space_group_name_H-M   P-1

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

_cell_length_a                   7.226(8)
_cell_length_b                   10.388(12)
_cell_length_c                   17.46(2)
_cell_angle_alpha                104.832(14)
_cell_angle_beta                 93.230(12)
_cell_angle_gamma                104.588(13)
_cell_volume                     1216(2)
_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            yellow
_exptl_crystal_size_max          0.25
_exptl_crystal_size_mid          0.25
_exptl_crystal_size_min          0.18
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.641
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             613
_exptl_absorpt_coefficient_mu    0.854
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.8148
_exptl_absorpt_correction_T_max  0.8614
_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  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            8606
_diffrn_reflns_av_R_equivalents  0.0372
_diffrn_reflns_av_sigmaI/netI    0.0539
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_theta_min         2.11
_diffrn_reflns_theta_max         25.05
_reflns_number_total             4153
_reflns_number_gt                3289
_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)+(0.0702P)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    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         4153
_refine_ls_number_parameters     358
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0577
_refine_ls_R_factor_gt           0.0443
_refine_ls_wR_factor_ref         0.1206
_refine_ls_wR_factor_gt          0.1110
_refine_ls_goodness_of_fit_ref   1.048
_refine_ls_restrained_S_all      1.048
_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
Mn1 Mn 0.42742(6) 0.31175(5) 0.20567(3) 0.02757(16) Uani 1 1 d . . .
Mn2 Mn 0.5000 1.5000 0.5000 0.02904(19) Uani 1 2 d S . .
O1 O 0.7246(3) 0.3579(2) 0.18439(13) 0.0372(5) Uani 1 1 d . . .
O2 O 1.0027(3) 0.5204(2) 0.20346(15) 0.0452(6) Uani 1 1 d . . .
O3 O 0.4786(3) 1.2175(2) 0.29491(12) 0.0372(5) Uani 1 1 d . . .
O4 O 0.3508(3) 1.3191(2) 0.39869(12) 0.0353(5) Uani 1 1 d . . .
O5 O 0.4100(3) 0.6513(2) 0.45378(12) 0.0353(5) Uani 1 1 d . . .
O6 O 0.1513(3) 0.6963(2) 0.50602(14) 0.0439(6) Uani 1 1 d . . .
O7 O 0.1430(3) 0.3137(2) 0.23092(13) 0.0407(6) Uani 1 1 d . . .
H1W H 0.1131 0.3755 0.2162 0.049 Uiso 1 1 d R . .
H2W H 0.0786 0.2887 0.2647 0.049 Uiso 1 1 d R . .
O8 O 0.7677(3) 1.5207(2) 0.44334(13) 0.0438(6) Uani 1 1 d . . .
H3W H 0.8223 1.4645 0.4519 0.053 Uiso 1 1 d R . .
H4W H 0.8487 1.5973 0.4666 0.053 Uiso 1 1 d R . .
O9 O 0.8900(4) 0.2077(3) 0.32401(17) 0.0670(8) Uani 1 1 d . . .
H5W H 0.9134 0.2389 0.3749 0.080 Uiso 1 1 d R . .
H6W H 0.8033 0.2503 0.3217 0.080 Uiso 1 1 d R . .
N1 N 0.5449(3) 0.5416(3) 0.25774(14) 0.0273(6) Uani 1 1 d . . .
N2 N 0.3494(3) 0.0982(3) 0.11549(14) 0.0305(6) Uani 1 1 d . . .
N3 N 0.3201(4) 0.3336(3) 0.08215(15) 0.0340(6) Uani 1 1 d . . .
C1 C 0.8291(4) 0.4808(3) 0.21169(18) 0.0306(7) Uani 1 1 d . . .
C2 C 0.7377(4) 0.5886(3) 0.25671(17) 0.0276(7) Uani 1 1 d . . .
C3 C 0.8386(4) 0.7233(3) 0.29291(18) 0.0323(7) Uani 1 1 d . . .
H3 H 0.9704 0.7528 0.2909 0.039 Uiso 1 1 calc R . .
C4 C 0.7437(4) 0.8155(3) 0.33257(18) 0.0333(7) Uani 1 1 d . . .
H4 H 0.8110 0.9073 0.3572 0.040 Uiso 1 1 calc R . .
C5 C 0.5459(4) 0.7693(3) 0.33526(16) 0.0258(6) Uani 1 1 d . . .
C6 C 0.4555(4) 0.6317(3) 0.29632(17) 0.0267(7) Uani 1 1 d . . .
H6 H 0.3235 0.5999 0.2971 0.032 Uiso 1 1 calc R . .
C7 C 0.4378(4) 0.8667(3) 0.37469(16) 0.0245(6) Uani 1 1 d . . .
C8 C 0.4605(4) 0.9882(3) 0.35198(17) 0.0275(7) Uani 1 1 d . . .
H8A H 0.5401 1.0028 0.3132 0.033 Uiso 1 1 calc R . .
C9 C 0.3689(4) 1.0891(3) 0.38480(17) 0.0273(7) Uani 1 1 d . . .
C10 C 0.2477(4) 1.0650(3) 0.44099(17) 0.0303(7) Uani 1 1 d . . .
H10 H 0.1847 1.1303 0.4639 0.036 Uiso 1 1 calc R . .
C11 C 0.2202(4) 0.9435(3) 0.46322(18) 0.0298(7) Uani 1 1 d . . .
H11 H 0.1364 0.9282 0.5005 0.036 Uiso 1 1 calc R . .
C12 C 0.3134(4) 0.8432(3) 0.43178(16) 0.0258(6) Uani 1 1 d . . .
C13 C 0.4017(4) 1.2204(3) 0.35874(17) 0.0291(7) Uani 1 1 d . . .
C14 C 0.2893(4) 0.7200(3) 0.46590(17) 0.0290(7) Uani 1 1 d . . .
C15 C 0.3599(5) -0.0183(3) 0.13149(19) 0.0375(8) Uani 1 1 d . . .
H15 H 0.4009 -0.0137 0.1838 0.045 Uiso 1 1 calc R . .
C16 C 0.3132(5) -0.1468(4) 0.0746(2) 0.0449(9) Uani 1 1 d . . .
H16 H 0.3228 -0.2254 0.0890 0.054 Uiso 1 1 calc R . .
C17 C 0.2532(5) -0.1558(4) -0.0026(2) 0.0413(8) Uani 1 1 d . . .
H17 H 0.2228 -0.2404 -0.0417 0.050 Uiso 1 1 calc R . .
C18 C 0.2383(4) -0.0353(4) -0.02210(19) 0.0350(8) Uani 1 1 d . . .
C19 C 0.2879(4) 0.0895(3) 0.03911(17) 0.0280(7) Uani 1 1 d . . .
C20 C 0.1736(5) -0.0371(4) -0.1010(2) 0.0438(9) Uani 1 1 d . . .
H20 H 0.1419 -0.1198 -0.1416 0.053 Uiso 1 1 calc R . .
C21 C 0.1580(5) 0.0806(4) -0.1173(2) 0.0461(9) Uani 1 1 d . . .
H21 H 0.1170 0.0777 -0.1693 0.055 Uiso 1 1 calc R . .
C22 C 0.2031(4) 0.2086(4) -0.05651(18) 0.0374(8) Uani 1 1 d . . .
C23 C 0.2715(4) 0.2149(3) 0.02150(17) 0.0311(7) Uani 1 1 d . . .
C24 C 0.1817(5) 0.3334(4) -0.0693(2) 0.0472(9) Uani 1 1 d . . .
H24 H 0.1357 0.3348 -0.1199 0.057 Uiso 1 1 calc R . .
C25 C 0.2278(6) 0.4498(4) -0.0085(2) 0.0523(10) Uani 1 1 d . . .
H25 H 0.2129 0.5318 -0.0168 0.063 Uiso 1 1 calc R . .
C26 C 0.2977(5) 0.4477(4) 0.0665(2) 0.0452(9) Uani 1 1 d . . .
H26 H 0.3303 0.5298 0.1077 0.054 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
Mn1 O3 2.103(3) 1_545 ?
Mn1 O7 2.130(3) . ?
Mn1 O1 2.154(3) . ?
Mn1 N1 2.243(3) . ?
Mn1 N2 2.280(3) . ?
Mn1 N3 2.336(3) . ?
Mn2 O5 2.157(3) 2_676 ?
Mn2 O5 2.157(3) 1_565 ?
Mn2 O8 2.209(3) . ?
Mn2 O8 2.209(3) 2_686 ?
Mn2 O4 2.210(3) . ?
Mn2 O4 2.210(3) 2_686 ?
O1 C1 1.261(4) . ?
O2 C1 1.247(4) . ?
O3 C13 1.271(4) . ?
O3 Mn1 2.103(3) 1_565 ?
O4 C13 1.236(4) . ?
O5 C14 1.254(4) . ?
O5 Mn2 2.157(3) 1_545 ?
O6 C14 1.260(4) . ?
O7 H1W 0.8200 . ?
O7 H2W 0.8245 . ?
O8 H3W 0.8200 . ?
O8 H4W 0.8456 . ?
O9 H5W 0.8550 . ?
O9 H6W 0.8574 . ?
N1 C6 1.333(4) . ?
N1 C2 1.358(4) . ?
N2 C15 1.329(4) . ?
N2 C19 1.355(4) . ?
N3 C26 1.329(4) . ?
N3 C23 1.355(4) . ?
C1 C2 1.512(4) . ?
C2 C3 1.368(5) . ?
C3 C4 1.382(4) . ?
C3 H3 0.9300 . ?
C4 C5 1.396(4) . ?
C4 H4 0.9300 . ?
C5 C6 1.383(4) . ?
C5 C7 1.487(4) . ?
C6 H6 0.9300 . ?
C7 C8 1.392(4) . ?
C7 C12 1.406(4) . ?
C8 C9 1.396(4) . ?
C8 H8A 0.9300 . ?
C9 C10 1.380(4) . ?
C9 C13 1.513(4) . ?
C10 C11 1.384(4) . ?
C10 H10 0.9300 . ?
C11 C12 1.394(4) . ?
C11 H11 0.9300 . ?
C12 C14 1.520(4) . ?
C15 C16 1.393(5) . ?
C15 H15 0.9300 . ?
C16 C17 1.365(5) . ?
C16 H16 0.9300 . ?
C17 C18 1.406(5) . ?
C17 H17 0.9300 . ?
C18 C19 1.402(5) . ?
C18 C20 1.423(5) . ?
C19 C23 1.443(5) . ?
C20 C21 1.355(5) . ?
C20 H20 0.9300 . ?
C21 C22 1.421(5) . ?
C21 H21 0.9300 . ?
C22 C23 1.402(4) . ?
C22 C24 1.415(5) . ?
C24 C25 1.342(6) . ?
C24 H24 0.9300 . ?
C25 C26 1.385(5) . ?
C25 H25 0.9300 . ?
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
O3 Mn1 O7 94.19(9) 1_545 . ?
O3 Mn1 O1 92.97(9) 1_545 . ?
O7 Mn1 O1 167.41(9) . . ?
O3 Mn1 N1 107.75(11) 1_545 . ?
O7 Mn1 N1 93.05(9) . . ?
O1 Mn1 N1 74.89(9) . . ?
O3 Mn1 N2 88.23(13) 1_545 . ?
O7 Mn1 N2 97.51(9) . . ?
O1 Mn1 N2 93.05(9) . . ?
N1 Mn1 N2 160.18(9) . . ?
O3 Mn1 N3 159.49(10) 1_545 . ?
O7 Mn1 N3 83.96(10) . . ?
O1 Mn1 N3 92.88(10) . . ?
N1 Mn1 N3 92.76(10) . . ?
N2 Mn1 N3 71.84(11) . . ?
O5 Mn2 O5 180.00(10) 2_676 1_565 ?
O5 Mn2 O8 85.70(10) 2_676 . ?
O5 Mn2 O8 94.30(10) 1_565 . ?
O5 Mn2 O8 94.30(10) 2_676 2_686 ?
O5 Mn2 O8 85.70(10) 1_565 2_686 ?
O8 Mn2 O8 179.999(1) . 2_686 ?
O5 Mn2 O4 84.04(12) 2_676 . ?
O5 Mn2 O4 95.96(12) 1_565 . ?
O8 Mn2 O4 90.12(10) . . ?
O8 Mn2 O4 89.88(10) 2_686 . ?
O5 Mn2 O4 95.96(12) 2_676 2_686 ?
O5 Mn2 O4 84.04(12) 1_565 2_686 ?
O8 Mn2 O4 89.88(10) . 2_686 ?
O8 Mn2 O4 90.12(10) 2_686 2_686 ?
O4 Mn2 O4 180.00(9) . 2_686 ?
C1 O1 Mn1 118.49(19) . . ?
C13 O3 Mn1 128.3(2) . 1_565 ?
C13 O4 Mn2 132.8(2) . . ?
C14 O5 Mn2 138.04(19) . 1_545 ?
Mn1 O7 H1W 109.4 . . ?
Mn1 O7 H2W 132.4 . . ?
H1W O7 H2W 113.6 . . ?
Mn2 O8 H3W 109.4 . . ?
Mn2 O8 H4W 110.3 . . ?
H3W O8 H4W 102.4 . . ?
H5W O9 H6W 92.5 . . ?
C6 N1 C2 117.6(3) . . ?
C6 N1 Mn1 128.4(2) . . ?
C2 N1 Mn1 113.52(19) . . ?
C15 N2 C19 117.3(3) . . ?
C15 N2 Mn1 125.5(2) . . ?
C19 N2 Mn1 117.2(2) . . ?
C26 N3 C23 117.9(3) . . ?
C26 N3 Mn1 126.9(2) . . ?
C23 N3 Mn1 115.2(2) . . ?
O2 C1 O1 124.5(3) . . ?
O2 C1 C2 117.4(3) . . ?
O1 C1 C2 118.0(3) . . ?
N1 C2 C3 122.0(3) . . ?
N1 C2 C1 114.6(3) . . ?
C3 C2 C1 123.4(3) . . ?
C2 C3 C4 119.7(3) . . ?
C2 C3 H3 120.2 . . ?
C4 C3 H3 120.2 . . ?
C3 C4 C5 119.4(3) . . ?
C3 C4 H4 120.3 . . ?
C5 C4 H4 120.3 . . ?
C6 C5 C4 116.9(3) . . ?
C6 C5 C7 122.2(3) . . ?
C4 C5 C7 120.8(3) . . ?
N1 C6 C5 124.4(3) . . ?
N1 C6 H6 117.8 . . ?
C5 C6 H6 117.8 . . ?
C8 C7 C12 118.4(3) . . ?
C8 C7 C5 117.0(3) . . ?
C12 C7 C5 124.6(3) . . ?
C7 C8 C9 122.9(3) . . ?
C7 C8 H8A 118.6 . . ?
C9 C8 H8A 118.6 . . ?
C10 C9 C8 118.1(3) . . ?
C10 C9 C13 121.3(3) . . ?
C8 C9 C13 120.6(3) . . ?
C9 C10 C11 119.9(3) . . ?
C9 C10 H10 120.1 . . ?
C11 C10 H10 120.1 . . ?
C10 C11 C12 122.5(3) . . ?
C10 C11 H11 118.8 . . ?
C12 C11 H11 118.8 . . ?
C11 C12 C7 118.2(3) . . ?
C11 C12 C14 118.5(3) . . ?
C7 C12 C14 123.1(3) . . ?
O4 C13 O3 125.2(3) . . ?
O4 C13 C9 119.4(3) . . ?
O3 C13 C9 115.4(3) . . ?
O5 C14 O6 124.7(3) . . ?
O5 C14 C12 117.9(3) . . ?
O6 C14 C12 117.4(3) . . ?
N2 C15 C16 123.9(3) . . ?
N2 C15 H15 118.1 . . ?
C16 C15 H15 118.1 . . ?
C17 C16 C15 119.0(3) . . ?
C17 C16 H16 120.5 . . ?
C15 C16 H16 120.5 . . ?
C16 C17 C18 119.0(3) . . ?
C16 C17 H17 120.5 . . ?
C18 C17 H17 120.5 . . ?
C19 C18 C17 118.1(3) . . ?
C19 C18 C20 119.8(3) . . ?
C17 C18 C20 122.1(3) . . ?
N2 C19 C18 122.7(3) . . ?
N2 C19 C23 117.7(3) . . ?
C18 C19 C23 119.5(3) . . ?
C21 C20 C18 120.5(3) . . ?
C21 C20 H20 119.7 . . ?
C18 C20 H20 119.7 . . ?
C20 C21 C22 121.3(3) . . ?
C20 C21 H21 119.4 . . ?
C22 C21 H21 119.4 . . ?
C23 C22 C24 116.5(3) . . ?
C23 C22 C21 119.7(3) . . ?
C24 C22 C21 123.8(3) . . ?
N3 C23 C22 123.0(3) . . ?
N3 C23 C19 117.9(3) . . ?
C22 C23 C19 119.1(3) . . ?
C25 C24 C22 119.9(3) . . ?
C25 C24 H24 120.0 . . ?
C22 C24 H24 120.0 . . ?
C24 C25 C26 119.9(4) . . ?
C24 C25 H25 120.0 . . ?
C26 C25 H25 120.0 . . ?
N3 C26 C25 122.8(4) . . ?
N3 C26 H26 118.6 . . ?
C25 C26 H26 118.6 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
O3 Mn1 O1 C1 -103.9(2) 1_545 . . . ?
O7 Mn1 O1 C1 20.7(5) . . . . ?
N1 Mn1 O1 C1 3.6(2) . . . . ?
N2 Mn1 O1 C1 167.7(2) . . . . ?
N3 Mn1 O1 C1 95.7(2) . . . . ?
O5 Mn2 O4 C13 -45.9(3) 2_676 . . . ?
O5 Mn2 O4 C13 134.1(3) 1_565 . . . ?
O8 Mn2 O4 C13 39.8(3) . . . . ?
O8 Mn2 O4 C13 -140.2(3) 2_686 . . . ?
O4 Mn2 O4 C13 -151(50) 2_686 . . . ?
O3 Mn1 N1 C6 -89.5(2) 1_545 . . . ?
O7 Mn1 N1 C6 5.9(2) . . . . ?
O1 Mn1 N1 C6 -177.8(3) . . . . ?
N2 Mn1 N1 C6 128.1(3) . . . . ?
N3 Mn1 N1 C6 90.0(2) . . . . ?
O3 Mn1 N1 C2 82.3(2) 1_545 . . . ?
O7 Mn1 N1 C2 177.68(19) . . . . ?
O1 Mn1 N1 C2 -5.99(18) . . . . ?
N2 Mn1 N1 C2 -60.1(3) . . . . ?
N3 Mn1 N1 C2 -98.2(2) . . . . ?
O3 Mn1 N2 C15 -3.7(2) 1_545 . . . ?
O7 Mn1 N2 C15 -97.6(2) . . . . ?
O1 Mn1 N2 C15 89.2(2) . . . . ?
N1 Mn1 N2 C15 140.8(3) . . . . ?
N3 Mn1 N2 C15 -178.7(3) . . . . ?
O3 Mn1 N2 C19 176.7(2) 1_545 . . . ?
O7 Mn1 N2 C19 82.7(2) . . . . ?
O1 Mn1 N2 C19 -90.4(2) . . . . ?
N1 Mn1 N2 C19 -38.9(4) . . . . ?
N3 Mn1 N2 C19 1.60(18) . . . . ?
O3 Mn1 N3 C26 162.7(3) 1_545 . . . ?
O7 Mn1 N3 C26 76.9(3) . . . . ?
O1 Mn1 N3 C26 -90.9(3) . . . . ?
N1 Mn1 N3 C26 -15.9(3) . . . . ?
N2 Mn1 N3 C26 176.8(3) . . . . ?
O3 Mn1 N3 C23 -15.4(4) 1_545 . . . ?
O7 Mn1 N3 C23 -101.2(2) . . . . ?
O1 Mn1 N3 C23 91.0(2) . . . . ?
N1 Mn1 N3 C23 166.0(2) . . . . ?
N2 Mn1 N3 C23 -1.27(19) . . . . ?
Mn1 O1 C1 O2 179.9(2) . . . . ?
Mn1 O1 C1 C2 -0.9(3) . . . . ?
C6 N1 C2 C3 -0.7(4) . . . . ?
Mn1 N1 C2 C3 -173.4(2) . . . . ?
C6 N1 C2 C1 -179.8(2) . . . . ?
Mn1 N1 C2 C1 7.4(3) . . . . ?
O2 C1 C2 N1 174.6(3) . . . . ?
O1 C1 C2 N1 -4.7(4) . . . . ?
O2 C1 C2 C3 -4.6(4) . . . . ?
O1 C1 C2 C3 176.2(3) . . . . ?
N1 C2 C3 C4 0.6(5) . . . . ?
C1 C2 C3 C4 179.7(3) . . . . ?
C2 C3 C4 C5 0.2(4) . . . . ?
C3 C4 C5 C6 -0.8(4) . . . . ?
C3 C4 C5 C7 -177.6(3) . . . . ?
C2 N1 C6 C5 0.0(4) . . . . ?
Mn1 N1 C6 C5 171.5(2) . . . . ?
C4 C5 C6 N1 0.8(4) . . . . ?
C7 C5 C6 N1 177.5(3) . . . . ?
C6 C5 C7 C8 -125.5(3) . . . . ?
C4 C5 C7 C8 51.2(4) . . . . ?
C6 C5 C7 C12 53.5(4) . . . . ?
C4 C5 C7 C12 -129.9(3) . . . . ?
C12 C7 C8 C9 1.6(4) . . . . ?
C5 C7 C8 C9 -179.4(3) . . . . ?
C7 C8 C9 C10 -1.4(4) . . . . ?
C7 C8 C9 C13 179.0(3) . . . . ?
C8 C9 C10 C11 0.0(4) . . . . ?
C13 C9 C10 C11 179.7(3) . . . . ?
C9 C10 C11 C12 1.1(4) . . . . ?
C10 C11 C12 C7 -0.8(4) . . . . ?
C10 C11 C12 C14 174.0(3) . . . . ?
C8 C7 C12 C11 -0.5(4) . . . . ?
C5 C7 C12 C11 -179.4(3) . . . . ?
C8 C7 C12 C14 -175.1(3) . . . . ?
C5 C7 C12 C14 6.0(4) . . . . ?
Mn2 O4 C13 O3 -90.7(3) . . . . ?
Mn2 O4 C13 C9 90.6(3) . . . . ?
Mn1 O3 C13 O4 -33.7(4) 1_565 . . . ?
Mn1 O3 C13 C9 145.0(2) 1_565 . . . ?
C10 C9 C13 O4 14.3(4) . . . . ?
C8 C9 C13 O4 -166.0(3) . . . . ?
C10 C9 C13 O3 -164.5(3) . . . . ?
C8 C9 C13 O3 15.1(4) . . . . ?
Mn2 O5 C14 O6 -13.7(5) 1_545 . . . ?
Mn2 O5 C14 C12 164.6(2) 1_545 . . . ?
C11 C12 C14 O5 -161.2(3) . . . . ?
C7 C12 C14 O5 13.3(4) . . . . ?
C11 C12 C14 O6 17.2(4) . . . . ?
C7 C12 C14 O6 -168.3(3) . . . . ?
C19 N2 C15 C16 0.5(5) . . . . ?
Mn1 N2 C15 C16 -179.2(2) . . . . ?
N2 C15 C16 C17 0.2(5) . . . . ?
C15 C16 C17 C18 -0.8(5) . . . . ?
C16 C17 C18 C19 0.6(5) . . . . ?
C16 C17 C18 C20 -178.9(3) . . . . ?
C15 N2 C19 C18 -0.6(4) . . . . ?
Mn1 N2 C19 C18 179.1(2) . . . . ?
C15 N2 C19 C23 178.5(3) . . . . ?
Mn1 N2 C19 C23 -1.8(3) . . . . ?
C17 C18 C19 N2 0.1(4) . . . . ?
C20 C18 C19 N2 179.6(3) . . . . ?
C17 C18 C19 C23 -179.1(3) . . . . ?
C20 C18 C19 C23 0.5(4) . . . . ?
C19 C18 C20 C21 -0.6(5) . . . . ?
C17 C18 C20 C21 178.9(3) . . . . ?
C18 C20 C21 C22 -0.7(5) . . . . ?
C20 C21 C22 C23 2.2(5) . . . . ?
C20 C21 C22 C24 -177.2(3) . . . . ?
C26 N3 C23 C22 1.3(4) . . . . ?
Mn1 N3 C23 C22 179.6(2) . . . . ?
C26 N3 C23 C19 -177.4(3) . . . . ?
Mn1 N3 C23 C19 0.9(3) . . . . ?
C24 C22 C23 N3 -1.5(4) . . . . ?
C21 C22 C23 N3 179.0(3) . . . . ?
C24 C22 C23 C19 177.2(3) . . . . ?
C21 C22 C23 C19 -2.3(4) . . . . ?
N2 C19 C23 N3 0.6(4) . . . . ?
C18 C19 C23 N3 179.8(3) . . . . ?
N2 C19 C23 C22 -178.2(2) . . . . ?
C18 C19 C23 C22 1.0(4) . . . . ?
C23 C22 C24 C25 0.6(5) . . . . ?
C21 C22 C24 C25 -180.0(3) . . . . ?
C22 C24 C25 C26 0.5(6) . . . . ?
C23 N3 C26 C25 -0.1(5) . . . . ?
Mn1 N3 C26 C25 -178.2(3) . . . . ?
C24 C25 C26 N3 -0.8(6) . . . . ?

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
O9 H6W O3 0.86 2.29 3.018(5) 143.4 1_545
O9 H5W O6 0.86 2.13 2.938(5) 156.7 2_666
O8 H4W O6 0.85 2.16 2.881(4) 143.6 1_665
O7 H2W O9 0.82 1.91 2.726(4) 167.9 1_455
O7 H1W O2 0.82 1.93 2.727(4) 165.4 1_455

_diffrn_measured_fraction_theta_max 0.963
_diffrn_reflns_theta_full        25.05
_diffrn_measured_fraction_theta_full 0.963
_refine_diff_density_max         0.692
_refine_diff_density_min         -0.461
_refine_diff_density_rms         0.081
####################################################################### 
# 
# 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_gu218_15co
_database_code_depnum_ccdc_archive 'CCDC 1057604'
_audit_update_record             
;
2015-04-02 deposited with the CCDC.
2015-10-08 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C28 H20 Co N2 O14'
_chemical_formula_weight         667.39

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'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_symmetry_cell_setting           Monoclinic
_symmetry_space_group_name_H-M   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                   16.9118(11)
_cell_length_b                   6.8877(6)
_cell_length_c                   11.8438(10)
_cell_angle_alpha                90.00
_cell_angle_beta                 105.872(9)
_cell_angle_gamma                90.00
_cell_volume                     1327.00(18)
_cell_formula_units_Z            2
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    ?
_cell_measurement_theta_min      ?
_cell_measurement_theta_max      ?

_exptl_crystal_description       needle
_exptl_crystal_colour            pink
_exptl_crystal_size_max          0.28
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.13
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.670
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             682
_exptl_absorpt_coefficient_mu    0.729
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.8219
_exptl_absorpt_correction_T_max  0.9112
_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  'Bruker APE-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            4550
_diffrn_reflns_av_R_equivalents  0.0495
_diffrn_reflns_av_sigmaI/netI    0.0842
_diffrn_reflns_limit_h_min       -20
_diffrn_reflns_limit_h_max       18
_diffrn_reflns_limit_k_min       -5
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_theta_min         3.45
_diffrn_reflns_theta_max         25.05
_reflns_number_total             2343
_reflns_number_gt                1717
_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)+(0.0306P)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    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         2343
_refine_ls_number_parameters     210
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0791
_refine_ls_R_factor_gt           0.0510
_refine_ls_wR_factor_ref         0.1049
_refine_ls_wR_factor_gt          0.0902
_refine_ls_goodness_of_fit_ref   1.064
_refine_ls_restrained_S_all      1.065
_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
Co1 Co 1.0000 0.5000 0.5000 0.0185(2) Uani 1 2 d S . .
O1 O 1.02219(13) 0.2609(4) 0.4127(2) 0.0227(6) Uani 1 1 d . . .
O2 O 0.96236(15) 0.0018(4) 0.3136(2) 0.0297(7) Uani 1 1 d . . .
O3 O 0.69814(17) -0.0818(5) 0.7696(3) 0.0481(9) Uani 1 1 d . . .
O4 O 0.80344(14) 0.0597(5) 0.7218(2) 0.0407(8) Uani 1 1 d . . .
H4 H 0.8295 -0.0311 0.7588 0.061 Uiso 1 1 calc R . .
O5 O 0.49748(15) 0.8120(4) 0.5954(2) 0.0343(7) Uani 1 1 d . . .
O6 O 0.58080(16) 0.8605(5) 0.4806(3) 0.0356(7) Uani 1 1 d D . .
O7 O 0.94056(13) 0.6235(4) 0.32729(18) 0.0225(6) Uani 1 1 d . . .
H1W H 0.9660 0.5793 0.2801 0.027 Uiso 1 1 d R . .
H2W H 0.9478 0.7461 0.3267 0.027 Uiso 1 1 d R . .
N1 N 0.89428(15) 0.3413(5) 0.4900(2) 0.0184(7) Uani 1 1 d . . .
C1 C 0.9639(2) 0.1399(6) 0.3816(3) 0.0200(9) Uani 1 1 d . . .
C2 C 0.8908(2) 0.1734(6) 0.4310(3) 0.0188(8) Uani 1 1 d . . .
C3 C 0.8248(2) 0.0491(6) 0.4136(3) 0.0247(9) Uani 1 1 d . . .
H1 H 0.8229 -0.0643 0.3704 0.030 Uiso 1 1 calc R . .
C4 C 0.7612(2) 0.0962(6) 0.4619(3) 0.0245(9) Uani 1 1 d . . .
H2 H 0.7168 0.0124 0.4529 0.029 Uiso 1 1 calc R . .
C5 C 0.76392(19) 0.2682(6) 0.5233(3) 0.0183(8) Uani 1 1 d . . .
C6 C 0.83207(19) 0.3883(6) 0.5354(3) 0.0197(8) Uani 1 1 d . . .
H3 H 0.8346 0.5046 0.5761 0.024 Uiso 1 1 calc R . .
C7 C 0.69855(19) 0.3309(6) 0.5786(3) 0.0211(9) Uani 1 1 d . . .
C8 C 0.67789(19) 0.2211(6) 0.6663(3) 0.0208(9) Uani 1 1 d . . .
C9 C 0.6139(2) 0.2828(6) 0.7101(3) 0.0273(10) Uani 1 1 d . . .
H5 H 0.5973 0.2055 0.7639 0.033 Uiso 1 1 calc R . .
C10 C 0.5742(2) 0.4576(6) 0.6750(3) 0.0276(10) Uani 1 1 d . . .
H7 H 0.5328 0.4994 0.7072 0.033 Uiso 1 1 calc R . .
C11 C 0.59659(19) 0.5699(6) 0.5917(3) 0.0221(9) Uani 1 1 d . . .
C12 C 0.65829(19) 0.5039(6) 0.5436(3) 0.0229(9) Uani 1 1 d . . .
H8 H 0.6726 0.5782 0.4866 0.028 Uiso 1 1 calc R . .
C13 C 0.7258(2) 0.0466(6) 0.7228(3) 0.0273(10) Uani 1 1 d . . .
C14 C 0.5557(2) 0.7592(6) 0.5546(3) 0.0255(9) Uani 1 1 d . . .
H6 H 0.551(3) 0.959(6) 0.453(5) 0.15(3) Uiso 1 1 d 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 O1 2.033(2) 3_766 ?
Co1 O1 2.033(2) . ?
Co1 N1 2.071(3) 3_766 ?
Co1 N1 2.071(3) . ?
Co1 O7 2.189(2) 3_766 ?
Co1 O7 2.189(2) . ?
O1 C1 1.266(4) . ?
O2 C1 1.242(4) . ?
O3 C13 1.204(4) . ?
O4 C13 1.320(4) . ?
O4 H4 0.8200 . ?
O5 C14 1.264(4) . ?
O6 C14 1.279(4) . ?
O6 H6 0.85(2) . ?
O7 H1W 0.8492 . ?
O7 H2W 0.8539 . ?
N1 C2 1.345(4) . ?
N1 C6 1.345(4) . ?
C1 C2 1.523(4) . ?
C2 C3 1.376(5) . ?
C3 C4 1.388(4) . ?
C3 H1 0.9300 . ?
C4 C5 1.385(5) . ?
C4 H2 0.9300 . ?
C5 C6 1.394(5) . ?
C5 C7 1.494(4) . ?
C6 H3 0.9300 . ?
C7 C12 1.379(5) . ?
C7 C8 1.404(5) . ?
C8 C9 1.389(4) . ?
C8 C13 1.501(5) . ?
C9 C10 1.386(5) . ?
C9 H5 0.9300 . ?
C10 C11 1.385(5) . ?
C10 H7 0.9300 . ?
C11 C12 1.395(4) . ?
C11 C14 1.484(5) . ?
C12 H8 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 Co1 O1 180.0 3_766 . ?
O1 Co1 N1 79.63(10) 3_766 3_766 ?
O1 Co1 N1 100.37(10) . 3_766 ?
O1 Co1 N1 100.37(10) 3_766 . ?
O1 Co1 N1 79.63(10) . . ?
N1 Co1 N1 180.0 3_766 . ?
O1 Co1 O7 86.62(9) 3_766 3_766 ?
O1 Co1 O7 93.38(9) . 3_766 ?
N1 Co1 O7 89.03(10) 3_766 3_766 ?
N1 Co1 O7 90.97(10) . 3_766 ?
O1 Co1 O7 93.38(9) 3_766 . ?
O1 Co1 O7 86.62(9) . . ?
N1 Co1 O7 90.97(10) 3_766 . ?
N1 Co1 O7 89.03(10) . . ?
O7 Co1 O7 180.0 3_766 . ?
C1 O1 Co1 116.3(2) . . ?
C13 O4 H4 109.5 . . ?
C14 O6 H6 115(4) . . ?
Co1 O7 H1W 106.9 . . ?
Co1 O7 H2W 111.2 . . ?
H1W O7 H2W 104.5 . . ?
C2 N1 C6 119.1(3) . . ?
C2 N1 Co1 113.5(2) . . ?
C6 N1 Co1 127.4(2) . . ?
O2 C1 O1 124.7(3) . . ?
O2 C1 C2 119.3(3) . . ?
O1 C1 C2 116.0(3) . . ?
N1 C2 C3 122.1(3) . . ?
N1 C2 C1 113.9(3) . . ?
C3 C2 C1 124.0(3) . . ?
C2 C3 C4 118.8(4) . . ?
C2 C3 H1 120.6 . . ?
C4 C3 H1 120.6 . . ?
C5 C4 C3 119.9(3) . . ?
C5 C4 H2 120.1 . . ?
C3 C4 H2 120.1 . . ?
C4 C5 C6 118.0(3) . . ?
C4 C5 C7 123.7(3) . . ?
C6 C5 C7 118.3(3) . . ?
N1 C6 C5 122.1(3) . . ?
N1 C6 H3 119.0 . . ?
C5 C6 H3 119.0 . . ?
C12 C7 C8 119.0(3) . . ?
C12 C7 C5 118.8(3) . . ?
C8 C7 C5 122.2(3) . . ?
C9 C8 C7 119.3(4) . . ?
C9 C8 C13 117.3(3) . . ?
C7 C8 C13 123.2(3) . . ?
C10 C9 C8 121.1(3) . . ?
C10 C9 H5 119.5 . . ?
C8 C9 H5 119.5 . . ?
C11 C10 C9 119.7(3) . . ?
C11 C10 H7 120.2 . . ?
C9 C10 H7 120.2 . . ?
C10 C11 C12 119.3(4) . . ?
C10 C11 C14 120.4(3) . . ?
C12 C11 C14 120.3(3) . . ?
C7 C12 C11 121.5(3) . . ?
C7 C12 H8 119.3 . . ?
C11 C12 H8 119.3 . . ?
O3 C13 O4 124.6(4) . . ?
O3 C13 C8 124.3(3) . . ?
O4 C13 C8 111.0(3) . . ?
O5 C14 O6 122.9(4) . . ?
O5 C14 C11 119.2(3) . . ?
O6 C14 C11 117.9(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
O1 Co1 O1 C1 145(12) 3_766 . . . ?
N1 Co1 O1 C1 -173.1(2) 3_766 . . . ?
N1 Co1 O1 C1 6.9(2) . . . . ?
O7 Co1 O1 C1 97.2(2) 3_766 . . . ?
O7 Co1 O1 C1 -82.8(2) . . . . ?
O1 Co1 N1 C2 177.7(2) 3_766 . . . ?
O1 Co1 N1 C2 -2.3(2) . . . . ?
N1 Co1 N1 C2 -147(29) 3_766 . . . ?
O7 Co1 N1 C2 -95.6(2) 3_766 . . . ?
O7 Co1 N1 C2 84.4(2) . . . . ?
O1 Co1 N1 C6 -2.6(3) 3_766 . . . ?
O1 Co1 N1 C6 177.4(3) . . . . ?
N1 Co1 N1 C6 33(29) 3_766 . . . ?
O7 Co1 N1 C6 84.2(3) 3_766 . . . ?
O7 Co1 N1 C6 -95.8(3) . . . . ?
Co1 O1 C1 O2 169.1(3) . . . . ?
Co1 O1 C1 C2 -9.7(4) . . . . ?
C6 N1 C2 C3 1.1(5) . . . . ?
Co1 N1 C2 C3 -179.1(3) . . . . ?
C6 N1 C2 C1 178.6(3) . . . . ?
Co1 N1 C2 C1 -1.7(4) . . . . ?
O2 C1 C2 N1 -171.3(3) . . . . ?
O1 C1 C2 N1 7.5(5) . . . . ?
O2 C1 C2 C3 6.1(5) . . . . ?
O1 C1 C2 C3 -175.1(3) . . . . ?
N1 C2 C3 C4 -2.1(5) . . . . ?
C1 C2 C3 C4 -179.2(3) . . . . ?
C2 C3 C4 C5 1.8(5) . . . . ?
C3 C4 C5 C6 -0.6(5) . . . . ?
C3 C4 C5 C7 -179.8(3) . . . . ?
C2 N1 C6 C5 0.1(5) . . . . ?
Co1 N1 C6 C5 -179.6(2) . . . . ?
C4 C5 C6 N1 -0.3(5) . . . . ?
C7 C5 C6 N1 178.9(3) . . . . ?
C4 C5 C7 C12 -120.6(4) . . . . ?
C6 C5 C7 C12 60.2(4) . . . . ?
C4 C5 C7 C8 60.6(5) . . . . ?
C6 C5 C7 C8 -118.6(4) . . . . ?
C12 C7 C8 C9 4.2(5) . . . . ?
C5 C7 C8 C9 -177.0(3) . . . . ?
C12 C7 C8 C13 -170.9(4) . . . . ?
C5 C7 C8 C13 7.9(5) . . . . ?
C7 C8 C9 C10 -4.8(5) . . . . ?
C13 C8 C9 C10 170.6(4) . . . . ?
C8 C9 C10 C11 2.4(6) . . . . ?
C9 C10 C11 C12 0.6(5) . . . . ?
C9 C10 C11 C14 -179.0(3) . . . . ?
C8 C7 C12 C11 -1.3(5) . . . . ?
C5 C7 C12 C11 179.9(3) . . . . ?
C10 C11 C12 C7 -1.2(5) . . . . ?
C14 C11 C12 C7 178.4(3) . . . . ?
C9 C8 C13 O3 28.2(6) . . . . ?
C7 C8 C13 O3 -156.5(4) . . . . ?
C9 C8 C13 O4 -147.3(3) . . . . ?
C7 C8 C13 O4 28.0(5) . . . . ?
C10 C11 C14 O5 -3.6(5) . . . . ?
C12 C11 C14 O5 176.8(3) . . . . ?
C10 C11 C14 O6 177.4(3) . . . . ?
C12 C11 C14 O6 -2.2(5) . . . . ?

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
O4 H4 O7 0.82 1.94 2.636(3) 142.4 4_566
O7 H1W O2 0.85 1.93 2.772(3) 171.3 2_755
O7 H2W O2 0.85 1.79 2.643(4) 175.5 1_565
O6 H6 O5 0.85(2) 1.80(2) 2.645(4) 171(7) 3_676

_diffrn_measured_fraction_theta_max 0.998
_diffrn_reflns_theta_full        25.05
_diffrn_measured_fraction_theta_full 0.998
_refine_diff_density_max         0.341
_refine_diff_density_min         -0.463
_refine_diff_density_rms         0.081
####################################################################### 
# 
# 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_gujzh_220_6mn
_database_code_depnum_ccdc_archive 'CCDC 1057605'
_audit_update_record             
;
2015-04-02 deposited with the CCDC.
2015-10-08 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C14 H9 Mn N O7'
_chemical_formula_weight         358.16

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           Orthorhombic
_symmetry_space_group_name_H-M   Pnna

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

_cell_length_a                   14.5661(10)
_cell_length_b                   25.0223(17)
_cell_length_c                   7.4491(6)
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_volume                     2715.0(3)
_cell_formula_units_Z            8
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    ?
_cell_measurement_theta_min      ?
_cell_measurement_theta_max      ?

_exptl_crystal_description       block
_exptl_crystal_colour            yellow
_exptl_crystal_size_max          0.28
_exptl_crystal_size_mid          0.26
_exptl_crystal_size_min          0.25
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.752
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1448
_exptl_absorpt_coefficient_mu    1.012
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.7648
_exptl_absorpt_correction_T_max  0.7860
_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  'Bruker APE-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            6744
_diffrn_reflns_av_R_equivalents  0.0389
_diffrn_reflns_av_sigmaI/netI    0.0486
_diffrn_reflns_limit_h_min       -17
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_k_min       -20
_diffrn_reflns_limit_k_max       29
_diffrn_reflns_limit_l_min       -8
_diffrn_reflns_limit_l_max       6
_diffrn_reflns_theta_min         3.48
_diffrn_reflns_theta_max         25.05
_reflns_number_total             2401
_reflns_number_gt                1817
_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)+(0.0462P)²+2.3460P] 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         2401
_refine_ls_number_parameters     210
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0577
_refine_ls_R_factor_gt           0.0412
_refine_ls_wR_factor_ref         0.1120
_refine_ls_wR_factor_gt          0.0975
_refine_ls_goodness_of_fit_ref   1.026
_refine_ls_restrained_S_all      1.026
_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
Mn1 Mn -0.05361(4) 0.2500 0.7500 0.0213(2) Uani 1 2 d S . .
Mn2 Mn 0.35620(4) 0.2500 0.7500 0.0180(2) Uani 1 2 d S . .
N1 N 0.25266(17) 0.31810(10) 0.7320(4) 0.0201(6) Uani 1 1 d . . .
O1 O -0.03486(15) 0.30501(9) 1.1889(3) 0.0302(6) Uani 1 1 d . . .
O2 O -0.00320(16) 0.31693(10) 0.8973(3) 0.0337(6) Uani 1 1 d . . .
O3 O 0.0667(2) 0.57168(10) 1.3541(4) 0.0531(8) Uani 1 1 d . . .
O4 O 0.16639(16) 0.57219(9) 1.1280(4) 0.0366(7) Uani 1 1 d . . .
H4 H 0.1770 0.6023 1.1660 0.055 Uiso 1 1 calc R . .
O5 O 0.34615(13) 0.27149(9) 0.4639(3) 0.0251(6) Uani 1 1 d . . .
O6 O 0.29835(16) 0.33107(9) 0.2644(3) 0.0301(6) Uani 1 1 d . . .
O7 O 0.0376(2) 0.20143(14) 0.9449(4) 0.0633(10) Uani 1 1 d . . .
H1W H 0.0089 0.1954 1.0373 0.076 Uiso 1 1 d R . .
H2W H 0.0095 0.1710 0.9373 0.076 Uiso 1 1 d R . .
C1 C -0.0028(2) 0.33138(12) 1.0576(5) 0.0213(7) Uani 1 1 d . . .
C2 C 0.0343(2) 0.38655(12) 1.1000(4) 0.0192(7) Uani 1 1 d . . .
C3 C -0.0087(2) 0.41395(14) 1.2394(4) 0.0253(8) Uani 1 1 d . . .
H3 H -0.0532 0.3967 1.3078 0.030 Uiso 1 1 calc R . .
C4 C 0.0139(2) 0.46635(13) 1.2772(5) 0.0252(8) Uani 1 1 d . . .
H4A H -0.0162 0.4842 1.3696 0.030 Uiso 1 1 calc R . .
C5 C 0.0810(2) 0.49273(12) 1.1788(5) 0.0217(7) Uani 1 1 d . . .
C6 C 0.1038(2) 0.54906(14) 1.2303(5) 0.0267(8) Uani 1 1 d . . .
C7 C 0.1250(2) 0.46560(12) 1.0404(5) 0.0224(7) Uani 1 1 d . . .
H7A H 0.1701 0.4831 0.9744 0.027 Uiso 1 1 calc R . .
C8 C 0.10322(19) 0.41226(12) 0.9978(4) 0.0198(7) Uani 1 1 d . . .
C9 C 0.15371(19) 0.38757(12) 0.8451(5) 0.0204(7) Uani 1 1 d . . .
C10 C 0.2044(2) 0.34016(12) 0.8654(5) 0.0217(7) Uani 1 1 d . . .
H10 H 0.2043 0.3234 0.9768 0.026 Uiso 1 1 calc R . .
C11 C 0.25017(19) 0.34142(12) 0.5680(4) 0.0194(7) Uani 1 1 d . . .
C12 C 0.3008(2) 0.31352(12) 0.4199(5) 0.0205(7) Uani 1 1 d . . .
C13 C 0.2036(2) 0.38885(13) 0.5377(5) 0.0273(8) Uani 1 1 d . . .
H13 H 0.2043 0.4049 0.4250 0.033 Uiso 1 1 calc R . .
C14 C 0.1560(2) 0.41196(14) 0.6787(5) 0.0288(8) Uani 1 1 d . . .
H14 H 0.1253 0.4441 0.6613 0.035 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
Mn1 O2 2.132(2) 3_556 ?
Mn1 O2 2.132(2) . ?
Mn1 O5 2.227(2) 6_556 ?
Mn1 O5 2.227(2) 8_566 ?
Mn1 O7 2.313(3) . ?
Mn1 O7 2.313(3) 3_556 ?
Mn2 O1 2.149(2) 6_657 ?
Mn2 O1 2.149(2) 8_665 ?
Mn2 O5 2.203(2) 3_556 ?
Mn2 O5 2.203(2) . ?
Mn2 N1 2.280(3) 3_556 ?
Mn2 N1 2.280(3) . ?
N1 C10 1.337(4) . ?
N1 C11 1.355(4) . ?
O1 C1 1.269(4) . ?
O1 Mn2 2.149(2) 6_557 ?
O2 C1 1.248(4) . ?
O3 C6 1.210(4) . ?
O4 C6 1.322(4) . ?
O4 H4 0.8200 . ?
O5 C12 1.284(4) . ?
O5 Mn1 2.227(2) 6_656 ?
O6 C12 1.239(4) . ?
O7 H1W 0.8200 . ?
O7 H2W 0.8655 . ?
C1 C2 1.516(4) . ?
C2 C3 1.393(4) . ?
C2 C8 1.414(4) . ?
C3 C4 1.381(5) . ?
C3 H3 0.9300 . ?
C4 C5 1.388(4) . ?
C4 H4A 0.9300 . ?
C5 C7 1.391(4) . ?
C5 C6 1.498(4) . ?
C7 C8 1.408(4) . ?
C7 H7A 0.9300 . ?
C8 C9 1.489(4) . ?
C9 C14 1.382(5) . ?
C9 C10 1.405(4) . ?
C10 H10 0.9300 . ?
C11 C13 1.385(4) . ?
C11 C12 1.499(4) . ?
C13 C14 1.385(5) . ?
C13 H13 0.9300 . ?
C14 H14 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 Mn1 O2 139.72(14) 3_556 . ?
O2 Mn1 O5 92.71(9) 3_556 6_556 ?
O2 Mn1 O5 113.84(9) . 6_556 ?
O2 Mn1 O5 113.84(9) 3_556 8_566 ?
O2 Mn1 O5 92.71(9) . 8_566 ?
O5 Mn1 O5 98.07(11) 6_556 8_566 ?
O2 Mn1 O7 73.28(10) 3_556 . ?
O2 Mn1 O7 83.80(11) . . ?
O5 Mn1 O7 162.28(11) 6_556 . ?
O5 Mn1 O7 78.51(9) 8_566 . ?
O2 Mn1 O7 83.80(11) 3_556 3_556 ?
O2 Mn1 O7 73.28(10) . 3_556 ?
O5 Mn1 O7 78.51(9) 6_556 3_556 ?
O5 Mn1 O7 162.27(11) 8_566 3_556 ?
O7 Mn1 O7 109.87(16) . 3_556 ?
O1 Mn2 O1 84.82(13) 6_657 8_665 ?
O1 Mn2 O5 90.03(9) 6_657 3_556 ?
O1 Mn2 O5 95.60(9) 8_665 3_556 ?
O1 Mn2 O5 95.60(9) 6_657 . ?
O1 Mn2 O5 90.03(9) 8_665 . ?
O5 Mn2 O5 172.38(11) 3_556 . ?
O1 Mn2 N1 162.69(10) 6_657 3_556 ?
O1 Mn2 N1 91.27(9) 8_665 3_556 ?
O5 Mn2 N1 73.54(9) 3_556 3_556 ?
O5 Mn2 N1 101.27(9) . 3_556 ?
O1 Mn2 N1 91.27(9) 6_657 . ?
O1 Mn2 N1 162.69(10) 8_665 . ?
O5 Mn2 N1 101.27(9) 3_556 . ?
O5 Mn2 N1 73.54(9) . . ?
N1 Mn2 N1 97.15(13) 3_556 . ?
C10 N1 C11 118.6(3) . . ?
C10 N1 Mn2 127.8(2) . . ?
C11 N1 Mn2 113.1(2) . . ?
C1 O1 Mn2 140.1(2) . 6_557 ?
C1 O2 Mn1 136.2(2) . . ?
C6 O4 H4 109.5 . . ?
C12 O5 Mn2 118.8(2) . . ?
C12 O5 Mn1 110.6(2) . 6_656 ?
Mn2 O5 Mn1 126.13(9) . 6_656 ?
Mn1 O7 H1W 109.3 . . ?
Mn1 O7 H2W 98.6 . . ?
H1W O7 H2W 69.5 . . ?
O2 C1 O1 125.8(3) . . ?
O2 C1 C2 117.7(3) . . ?
O1 C1 C2 116.4(3) . . ?
C3 C2 C8 119.8(3) . . ?
C3 C2 C1 116.3(3) . . ?
C8 C2 C1 123.7(3) . . ?
C4 C3 C2 120.8(3) . . ?
C4 C3 H3 119.6 . . ?
C2 C3 H3 119.6 . . ?
C3 C4 C5 120.7(3) . . ?
C3 C4 H4A 119.6 . . ?
C5 C4 H4A 119.6 . . ?
C4 C5 C7 118.9(3) . . ?
C4 C5 C6 117.9(3) . . ?
C7 C5 C6 123.1(3) . . ?
O3 C6 O4 122.9(3) . . ?
O3 C6 C5 122.4(3) . . ?
O4 C6 C5 114.7(3) . . ?
C5 C7 C8 121.7(3) . . ?
C5 C7 H7A 119.2 . . ?
C8 C7 H7A 119.2 . . ?
C7 C8 C2 118.0(3) . . ?
C7 C8 C9 117.0(3) . . ?
C2 C8 C9 124.9(3) . . ?
C14 C9 C10 117.2(3) . . ?
C14 C9 C8 120.9(3) . . ?
C10 C9 C8 121.8(3) . . ?
N1 C10 C9 123.0(3) . . ?
N1 C10 H10 118.5 . . ?
C9 C10 H10 118.5 . . ?
N1 C11 C13 121.9(3) . . ?
N1 C11 C12 116.7(3) . . ?
C13 C11 C12 121.3(3) . . ?
O6 C12 O5 122.9(3) . . ?
O6 C12 C11 120.5(3) . . ?
O5 C12 C11 116.5(3) . . ?
C14 C13 C11 118.7(3) . . ?
C14 C13 H13 120.7 . . ?
C11 C13 H13 120.7 . . ?
C9 C14 C13 120.5(3) . . ?
C9 C14 H14 119.7 . . ?
C13 C14 H14 119.7 . . ?

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 Mn2 N1 C10 -86.6(3) 6_657 . . . ?
O1 Mn2 N1 C10 -163.2(3) 8_665 . . . ?
O5 Mn2 N1 C10 3.7(3) 3_556 . . . ?
O5 Mn2 N1 C10 177.9(3) . . . . ?
N1 Mn2 N1 C10 78.2(2) 3_556 . . . ?
O1 Mn2 N1 C11 85.4(2) 6_657 . . . ?
O1 Mn2 N1 C11 8.8(4) 8_665 . . . ?
O5 Mn2 N1 C11 175.7(2) 3_556 . . . ?
O5 Mn2 N1 C11 -10.1(2) . . . . ?
N1 Mn2 N1 C11 -109.8(2) 3_556 . . . ?
O2 Mn1 O2 C1 -112.1(3) 3_556 . . . ?
O5 Mn1 O2 C1 121.0(3) 6_556 . . . ?
O5 Mn1 O2 C1 20.9(3) 8_566 . . . ?
O7 Mn1 O2 C1 -57.2(3) . . . . ?
O7 Mn1 O2 C1 -170.1(4) 3_556 . . . ?
O1 Mn2 O5 C12 -80.9(2) 6_657 . . . ?
O1 Mn2 O5 C12 -165.7(2) 8_665 . . . ?
O5 Mn2 O5 C12 56.5(2) 3_556 . . . ?
N1 Mn2 O5 C12 103.0(2) 3_556 . . . ?
N1 Mn2 O5 C12 8.8(2) . . . . ?
O1 Mn2 O5 Mn1 72.97(13) 6_657 . . 6_656 ?
O1 Mn2 O5 Mn1 -11.84(13) 8_665 . . 6_656 ?
O5 Mn2 O5 Mn1 -149.58(12) 3_556 . . 6_656 ?
N1 Mn2 O5 Mn1 -103.14(13) 3_556 . . 6_656 ?
N1 Mn2 O5 Mn1 162.64(14) . . . 6_656 ?
Mn1 O2 C1 O1 2.4(5) . . . . ?
Mn1 O2 C1 C2 -174.1(2) . . . . ?
Mn2 O1 C1 O2 -33.0(5) 6_557 . . . ?
Mn2 O1 C1 C2 143.5(3) 6_557 . . . ?
O2 C1 C2 C3 144.7(3) . . . . ?
O1 C1 C2 C3 -32.1(4) . . . . ?
O2 C1 C2 C8 -29.9(4) . . . . ?
O1 C1 C2 C8 153.3(3) . . . . ?
C8 C2 C3 C4 1.2(5) . . . . ?
C1 C2 C3 C4 -173.6(3) . . . . ?
C2 C3 C4 C5 -0.9(5) . . . . ?
C3 C4 C5 C7 0.3(5) . . . . ?
C3 C4 C5 C6 -178.4(3) . . . . ?
C4 C5 C6 O3 0.7(5) . . . . ?
C7 C5 C6 O3 -177.9(4) . . . . ?
C4 C5 C6 O4 -178.3(3) . . . . ?
C7 C5 C6 O4 3.2(5) . . . . ?
C4 C5 C7 C8 0.1(5) . . . . ?
C6 C5 C7 C8 178.7(3) . . . . ?
C5 C7 C8 C2 0.2(5) . . . . ?
C5 C7 C8 C9 179.0(3) . . . . ?
C3 C2 C8 C7 -0.8(4) . . . . ?
C1 C2 C8 C7 173.6(3) . . . . ?
C3 C2 C8 C9 -179.5(3) . . . . ?
C1 C2 C8 C9 -5.1(5) . . . . ?
C7 C8 C9 C14 -53.4(4) . . . . ?
C2 C8 C9 C14 125.3(4) . . . . ?
C7 C8 C9 C10 123.5(3) . . . . ?
C2 C8 C9 C10 -57.8(4) . . . . ?
C11 N1 C10 C9 -2.4(4) . . . . ?
Mn2 N1 C10 C9 169.2(2) . . . . ?
C14 C9 C10 N1 -0.8(5) . . . . ?
C8 C9 C10 N1 -177.8(3) . . . . ?
C10 N1 C11 C13 3.8(4) . . . . ?
Mn2 N1 C11 C13 -169.0(2) . . . . ?
C10 N1 C11 C12 -176.5(3) . . . . ?
Mn2 N1 C11 C12 10.7(3) . . . . ?
Mn2 O5 C12 O6 173.6(2) . . . . ?
Mn1 O5 C12 O6 15.9(4) 6_656 . . . ?
Mn2 O5 C12 C11 -6.1(3) . . . . ?
Mn1 O5 C12 C11 -163.8(2) 6_656 . . . ?
N1 C11 C12 O6 176.7(3) . . . . ?
C13 C11 C12 O6 -3.6(4) . . . . ?
N1 C11 C12 O5 -3.6(4) . . . . ?
C13 C11 C12 O5 176.1(3) . . . . ?
N1 C11 C13 C14 -2.1(5) . . . . ?
C12 C11 C13 C14 178.3(3) . . . . ?
C10 C9 C14 C13 2.5(5) . . . . ?
C8 C9 C14 C13 179.6(3) . . . . ?
C11 C13 C14 C9 -1.2(5) . . . . ?

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
O7 H1W O1 0.82 2.14 2.930(4) 162.6 3_557
O4 H4 O6 0.82 1.86 2.675(3) 176.9 2_566

_diffrn_measured_fraction_theta_max 0.997
_diffrn_reflns_theta_full        25.05
_diffrn_measured_fraction_theta_full 0.997
_refine_diff_density_max         0.326
_refine_diff_density_min         -0.389
_refine_diff_density_rms         0.074
####################################################################### 
# 
# 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_222_8zn_twin1_hklf4
_database_code_depnum_ccdc_archive 'CCDC 1057606'
_audit_update_record             
;
2015-04-02 deposited with the CCDC.
2015-10-08 downloaded from the CCDC.
;
_audit_creation_date             2015-03-06
_audit_creation_method           
;
Olex2 1.2
(compiled 2015.01.26 svn.r3150 for OlexSys, GUI svn.r4998)
;
_chemical_name_common            ?
_chemical_name_systematic        
;
 ? 
;
_chemical_formula_moiety         '0.5(C56 H48 N4 O36 Zn6)'
_chemical_formula_sum            'C28 H24 N2 O18 Zn3'
_chemical_formula_weight         872.60
_chemical_melting_point          ?
_chemical_oxdiff_formula         'C11 H10 N O'
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Zn Zn 0.2839 1.4301 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      monoclinic
_space_group_IT_number           15
_space_group_name_H-M_alt        'C 1 2/c 1'
_space_group_name_Hall           '-C 2yc'
loop_
_space_group_symop_id
_space_group_symop_operation_xyz
1 'x, y, z'
2 '-x, y, -z+1/2'
3 'x+1/2, y+1/2, z'
4 '-x+1/2, y+1/2, -z+1/2'
5 '-x, -y, -z'
6 'x, -y, z-1/2'
7 '-x+1/2, -y+1/2, -z'
8 'x+1/2, -y+1/2, z-1/2'

_cell_length_a                   29.702(3)
_cell_length_b                   6.1660(3)
_cell_length_c                   16.6016(8)
_cell_angle_alpha                90.00
_cell_angle_beta                 94.853(6)
_cell_angle_gamma                90.00
_cell_volume                     3029.5(3)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    2073
_cell_measurement_temperature    290.92(10)
_cell_measurement_theta_max      28.7050
_cell_measurement_theta_min      4.7460
_exptl_absorpt_coefficient_mu    2.448
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.91251
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET)
(compiled Feb  1 2013,16:14:44)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            'clear light colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.913
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             1760
_exptl_crystal_size_max          0.28
_exptl_crystal_size_mid          0.25
_exptl_crystal_size_min          0.24
_exptl_special_details           
;
 ? 
;
_diffrn_reflns_av_R_equivalents  0.0000
_diffrn_reflns_av_unetI/netI     0.0806
_diffrn_reflns_limit_h_max       36
_diffrn_reflns_limit_h_min       -36
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_number            3310
_diffrn_reflns_theta_full        25.50
_diffrn_reflns_theta_max         26.02
_diffrn_reflns_theta_min         3.37
_diffrn_ambient_temperature      290.92(10)
_diffrn_detector_area_resol_mean 16.0733
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_details      
;
#__ type_ start__ end____ width___ exp.time_
  1 omega   -2.00   24.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      -16.3571   57.0000   90.0000 26

#__ type_ start__ end____ width___ exp.time_
  2 omega  -17.00   26.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      -16.3571  -99.0000 -120.0000 43

#__ type_ start__ end____ width___ exp.time_
  3 omega   35.00   94.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -       19.7946  178.0000  -90.0000 59

#__ type_ start__ end____ width___ exp.time_
  4 omega  -51.00   64.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -       19.7946  -19.0000 -150.0000 115
;
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, Eos'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_UB_11      0.0136935000
_diffrn_orient_matrix_UB_12      0.0642944000
_diffrn_orient_matrix_UB_13      -0.0235793000
_diffrn_orient_matrix_UB_21      -0.0133688000
_diffrn_orient_matrix_UB_22      0.0922450000
_diffrn_orient_matrix_UB_23      0.0071920000
_diffrn_orient_matrix_UB_31      0.0144277000
_diffrn_orient_matrix_UB_32      0.0243220000
_diffrn_orient_matrix_UB_33      0.0350901000
loop_
_diffrn_oxdiff_twin_id
_diffrn_oxdiff_twin_ratio
_diffrn_oxdiff_twin_reflns_isolated
_diffrn_oxdiff_twin_reflns_overlapped
1 0.8250 1826 5568
2 0.1750 0 5567

_diffrn_radiation_monochromator  mirror
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'SuperNova (Mo) X-ray Source'
_diffrn_standards_decay_%        ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_number         ?
_reflns_number_gt                2471
_reflns_number_total             3310
_reflns_threshold_expression     >2sigma(I)
_computing_cell_refinement       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET)
(compiled Feb  1 2013,16:14:44)
;
_computing_data_collection       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET)
(compiled Feb  1 2013,16:14:44)
;
_computing_data_reduction        
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET)
(compiled Feb  1 2013,16:14:44)
;
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2008)'
_computing_structure_solution    'ShelXS (Sheldrick, 2008)'
_refine_diff_density_max         0.579
_refine_diff_density_min         -0.573
_refine_diff_density_rms         0.111
_refine_ls_extinction_coef       ?
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.950
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     235
_refine_ls_number_reflns         3310
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0582
_refine_ls_R_factor_gt           0.0395
_refine_ls_restrained_S_all      0.950
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0339P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0784
_refine_ls_wR_factor_ref         0.0817
_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. 
;
_olex2_refinement_description    
;
1. Twinned data refinement
 Scales: 0.8515(10) 0.1485(10)
2. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All O(H,H) groups
3.a Rotating group:
 O7(H7A,H7B), O8(H8A,H8B), O9(H9A,H9B)
3.b Aromatic/amide H refined with riding coordinates:
 C13(H13), C3(H3), C14(H14), C8(H8), C10(H10), C4(H4)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
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_calc_flag
_atom_site_disorder_assembly
_atom_site_disorder_group
_atom_site_site_symmetry_order
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
Zn1 Zn 0.330624(17) 1.08276(7) 0.24256(3) 0.01280(14) Uani 1 d . . 1 . . .
Zn2 Zn 0.5000 0.12038(11) 0.7500 0.01453(18) Uani 1 d . . 2 S T P
O1 O 0.31615(10) 0.9123(4) 0.33619(14) 0.0163(7) Uani 1 d . . 1 . . .
O7 O 0.38531(10) 1.2641(5) 0.25559(16) 0.0205(7) Uani 1 d . . 1 . . .
H7A H 0.4080 1.1967 0.2831 0.031 Uiso 1 d . . 1 GR . .
H7B H 0.3802 1.3845 0.2822 0.031 Uiso 1 d . . 1 GR . .
O5 O 0.51892(11) -0.3765(5) 0.59305(16) 0.0256(8) Uani 1 d . . 1 . . .
C1 C 0.33944(14) 0.7384(7) 0.3426(2) 0.0131(10) Uani 1 d . . 1 . . .
O8 O 0.28413(9) 1.3126(5) 0.24122(16) 0.0204(7) Uani 1 d . . 1 . . .
H8A H 0.2586 1.2571 0.2499 0.031 Uiso 1 d . . 1 GR . .
H8B H 0.2818 1.3746 0.1949 0.031 Uiso 1 d . . 1 GR . .
N1 N 0.45779(11) 0.0902(5) 0.64053(18) 0.0142(8) Uani 1 d . . 1 . . .
O9 O 0.45782(10) 0.3479(5) 0.79263(16) 0.0237(7) Uani 1 d . . 1 . . .
H9A H 0.4319 0.2897 0.8003 0.035 Uiso 1 d . . 1 GR . .
H9B H 0.4532 0.4536 0.7583 0.035 Uiso 1 d . . 1 GR . .
O2 O 0.36834(10) 0.6905(5) 0.29489(16) 0.0191(7) Uani 1 d . . 1 . . .
O6 O 0.53335(10) -0.1268(5) 0.68939(16) 0.0213(7) Uani 1 d . . 1 . . .
C11 C 0.46959(14) -0.0755(7) 0.5945(2) 0.0128(9) Uani 1 d . . 1 . . .
C2 C 0.33145(14) 0.5906(6) 0.4117(2) 0.0123(9) Uani 1 d . . 1 . . .
C13 C 0.44710(15) -0.1233(7) 0.5204(2) 0.0177(10) Uani 1 d . . 1 . . .
H13 H 0.4557 -0.2405 0.4899 0.021 Uiso 1 calc . . 1 R . .
C12 C 0.51023(15) -0.2065(7) 0.6276(2) 0.0175(10) Uani 1 d . . 1 . . .
C3 C 0.29078(15) 0.5986(7) 0.4466(2) 0.0157(10) Uani 1 d . . 1 . . .
H3 H 0.2675 0.6873 0.4249 0.019 Uiso 1 calc . . 1 R . .
C14 C 0.41134(15) 0.0092(7) 0.4931(2) 0.0189(10) Uani 1 d . . 1 . . .
H14 H 0.3960 -0.0171 0.4429 0.023 Uiso 1 calc . . 1 R . .
C8 C 0.36535(14) 0.4530(6) 0.4430(2) 0.0123(9) Uani 1 d . . 1 . . .
H8 H 0.3924 0.4465 0.4185 0.015 Uiso 1 calc . . 1 R . .
C9 C 0.39827(14) 0.1788(6) 0.5393(2) 0.0123(9) Uani 1 d . . 1 . . .
C7 C 0.35980(14) 0.3228(6) 0.5111(2) 0.0105(9) Uani 1 d . . 1 . . .
C10 C 0.42285(14) 0.2147(7) 0.6138(2) 0.0145(10) Uani 1 d . . 1 . . .
H10 H 0.4146 0.3293 0.6459 0.017 Uiso 1 calc . . 1 R . .
C5 C 0.31928(14) 0.3397(6) 0.5481(2) 0.0121(9) Uani 1 d . . 1 . . .
C4 C 0.28502(14) 0.4736(6) 0.5141(2) 0.0147(9) Uani 1 d . . 1 . . .
H4 H 0.2576 0.4790 0.5373 0.018 Uiso 1 calc . . 1 R . .
O4 O 0.28289(10) 0.2928(4) 0.66745(15) 0.0152(7) Uani 1 d . . 1 . . .
C6 C 0.30970(14) 0.2131(7) 0.6225(2) 0.0125(9) Uani 1 d . . 1 . . .
O3 O 0.33037(10) 0.0356(4) 0.63453(14) 0.0158(7) Uani 1 d . . 1 . . .


_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 O1 1.954(3) . ?
Zn1 O7 1.969(3) . ?
Zn1 O8 1.977(3) . ?
Zn1 O3 1.935(2) 6_565 ?
Zn2 N1 2.127(3) . ?
Zn2 N1 2.127(3) 2_656 ?
Zn2 O9 2.046(3) 2_656 ?
Zn2 O9 2.046(3) . ?
Zn2 O6 2.118(3) . ?
Zn2 O6 2.118(3) 2_656 ?
O1 C1 1.276(5) . ?
O7 H7A 0.8844 . ?
O7 H7B 0.8836 . ?
O5 C12 1.232(5) . ?
C1 O2 1.252(5) . ?
C1 C2 1.499(5) . ?
O8 H8A 0.8565 . ?
O8 H8B 0.8568 . ?
N1 C11 1.340(5) . ?
N1 C10 1.336(5) . ?
O9 H9A 0.8686 . ?
O9 H9B 0.8699 . ?
O6 C12 1.283(5) . ?
C11 C13 1.381(5) . ?
C11 C12 1.517(6) . ?
C2 C3 1.384(6) . ?
C2 C8 1.384(5) . ?
C13 H13 0.9300 . ?
C13 C14 1.386(6) . ?
C3 H3 0.9300 . ?
C3 C4 1.382(5) . ?
C14 H14 0.9300 . ?
C14 C9 1.372(6) . ?
C8 H8 0.9300 . ?
C8 C7 1.408(5) . ?
C9 C7 1.491(5) . ?
C9 C10 1.400(5) . ?
C7 C5 1.400(6) . ?
C10 H10 0.9300 . ?
C5 C4 1.392(5) . ?
C5 C6 1.509(5) . ?
C4 H4 0.9300 . ?
O4 C6 1.239(5) . ?
C6 O3 1.262(5) . ?
O3 Zn1 1.936(2) 6_566 ?

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 Zn1 O7 116.94(11) . . ?
O1 Zn1 O8 101.18(12) . . ?
O7 Zn1 O8 99.39(12) . . ?
O3 Zn1 O1 123.40(11) 6_565 . ?
O3 Zn1 O7 104.75(12) 6_565 . ?
O3 Zn1 O8 108.16(11) 6_565 . ?
N1 Zn2 N1 169.96(19) . 2_656 ?
O9 Zn2 N1 91.24(12) . . ?
O9 Zn2 N1 95.64(12) 2_656 . ?
O9 Zn2 N1 91.24(12) 2_656 2_656 ?
O9 Zn2 N1 95.64(12) . 2_656 ?
O9 Zn2 O9 93.46(18) . 2_656 ?
O9 Zn2 O6 169.17(10) 2_656 2_656 ?
O9 Zn2 O6 90.25(12) 2_656 . ?
O9 Zn2 O6 169.17(10) . . ?
O9 Zn2 O6 90.26(12) . 2_656 ?
O6 Zn2 N1 94.44(12) 2_656 . ?
O6 Zn2 N1 94.44(12) . 2_656 ?
O6 Zn2 N1 78.26(12) . . ?
O6 Zn2 N1 78.27(11) 2_656 2_656 ?
O6 Zn2 O6 87.93(17) . 2_656 ?
C1 O1 Zn1 111.4(3) . . ?
Zn1 O7 H7A 112.0 . . ?
Zn1 O7 H7B 110.9 . . ?
H7A O7 H7B 107.1 . . ?
O1 C1 C2 117.1(4) . . ?
O2 C1 O1 122.8(4) . . ?
O2 C1 C2 120.1(4) . . ?
Zn1 O8 H8A 109.9 . . ?
Zn1 O8 H8B 109.4 . . ?
H8A O8 H8B 109.0 . . ?
C11 N1 Zn2 113.0(3) . . ?
C10 N1 Zn2 128.2(3) . . ?
C10 N1 C11 118.8(3) . . ?
Zn2 O9 H9A 110.1 . . ?
Zn2 O9 H9B 110.8 . . ?
H9A O9 H9B 108.2 . . ?
C12 O6 Zn2 114.5(3) . . ?
N1 C11 C13 122.7(4) . . ?
N1 C11 C12 116.0(3) . . ?
C13 C11 C12 121.3(4) . . ?
C3 C2 C1 120.0(4) . . ?
C8 C2 C1 120.2(4) . . ?
C8 C2 C3 119.8(4) . . ?
C11 C13 H13 121.2 . . ?
C11 C13 C14 117.7(4) . . ?
C14 C13 H13 121.2 . . ?
O5 C12 O6 125.4(4) . . ?
O5 C12 C11 118.4(4) . . ?
O6 C12 C11 116.2(4) . . ?
C2 C3 H3 120.3 . . ?
C4 C3 C2 119.5(4) . . ?
C4 C3 H3 120.3 . . ?
C13 C14 H14 119.6 . . ?
C9 C14 C13 120.8(4) . . ?
C9 C14 H14 119.6 . . ?
C2 C8 H8 119.3 . . ?
C2 C8 C7 121.3(4) . . ?
C7 C8 H8 119.3 . . ?
C14 C9 C7 121.6(3) . . ?
C14 C9 C10 117.6(4) . . ?
C10 C9 C7 120.8(4) . . ?
C8 C7 C9 117.0(4) . . ?
C5 C7 C8 118.2(4) . . ?
C5 C7 C9 124.8(4) . . ?
N1 C10 C9 122.3(4) . . ?
N1 C10 H10 118.8 . . ?
C9 C10 H10 118.8 . . ?
C7 C5 C6 123.3(4) . . ?
C4 C5 C7 119.5(4) . . ?
C4 C5 C6 117.2(4) . . ?
C3 C4 C5 121.5(4) . . ?
C3 C4 H4 119.2 . . ?
C5 C4 H4 119.2 . . ?
O4 C6 C5 117.6(4) . . ?
O4 C6 O3 125.3(4) . . ?
O3 C6 C5 117.1(4) . . ?
C6 O3 Zn1 115.9(2) . 6_566 ?

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
Zn1 O1 C1 O2 1.5(4) . . . . ?
Zn1 O1 C1 C2 -179.5(2) . . . . ?
Zn2 N1 C11 C13 -179.3(3) . . . . ?
Zn2 N1 C11 C12 -0.6(5) . . . . ?
Zn2 N1 C10 C9 178.8(3) . . . . ?
Zn2 O6 C12 O5 -165.3(4) . . . . ?
Zn2 O6 C12 C11 16.0(5) . . . . ?
O1 C1 C2 C3 23.4(5) . . . . ?
O1 C1 C2 C8 -153.7(4) . . . . ?
O7 Zn1 O1 C1 -80.8(3) . . . . ?
C1 C2 C3 C4 -175.1(3) . . . . ?
C1 C2 C8 C7 175.9(3) . . . . ?
O8 Zn1 O1 C1 172.6(2) . . . . ?
N1 Zn2 N1 C11 -37.4(3) 2_656 . . . ?
N1 Zn2 N1 C10 143.4(4) 2_656 . . . ?
N1 Zn2 O6 C12 -12.6(3) . . . . ?
N1 Zn2 O6 C12 160.4(3) 2_656 . . . ?
N1 C11 C13 C14 0.9(7) . . . . ?
N1 C11 C12 O5 170.7(4) . . . . ?
N1 C11 C12 O6 -10.4(6) . . . . ?
O9 Zn2 N1 C11 95.6(3) 2_656 . . . ?
O9 Zn2 N1 C11 -170.8(3) . . . . ?
O9 Zn2 N1 C10 10.1(4) . . . . ?
O9 Zn2 N1 C10 -83.5(4) 2_656 . . . ?
O9 Zn2 O6 C12 -108.3(3) 2_656 . . . ?
O9 Zn2 O6 C12 1.9(8) . . . . ?
O2 C1 C2 C3 -157.5(4) . . . . ?
O2 C1 C2 C8 25.4(5) . . . . ?
O6 Zn2 N1 C11 6.5(3) . . . . ?
O6 Zn2 N1 C11 -80.4(3) 2_656 . . . ?
O6 Zn2 N1 C10 -172.6(4) . . . . ?
O6 Zn2 N1 C10 100.4(4) 2_656 . . . ?
O6 Zn2 O6 C12 82.4(3) 2_656 . . . ?
C11 N1 C10 C9 -0.3(6) . . . . ?
C11 C13 C14 C9 -1.5(7) . . . . ?
C2 C3 C4 C5 0.2(6) . . . . ?
C2 C8 C7 C9 179.4(4) . . . . ?
C2 C8 C7 C5 -1.6(6) . . . . ?
C13 C11 C12 O5 -10.6(6) . . . . ?
C13 C11 C12 O6 168.2(4) . . . . ?
C13 C14 C9 C7 -179.9(4) . . . . ?
C13 C14 C9 C10 1.2(7) . . . . ?
C12 C11 C13 C14 -177.6(4) . . . . ?
C3 C2 C8 C7 -1.3(6) . . . . ?
C14 C9 C7 C8 -65.9(5) . . . . ?
C14 C9 C7 C5 115.1(5) . . . . ?
C14 C9 C10 N1 -0.3(6) . . . . ?
C8 C2 C3 C4 2.0(6) . . . . ?
C8 C7 C5 C4 3.7(6) . . . . ?
C8 C7 C5 C6 -178.5(3) . . . . ?
C9 C7 C5 C4 -177.4(4) . . . . ?
C9 C7 C5 C6 0.4(6) . . . . ?
C7 C9 C10 N1 -179.3(4) . . . . ?
C7 C5 C4 C3 -3.1(6) . . . . ?
C7 C5 C6 O4 152.9(4) . . . . ?
C7 C5 C6 O3 -25.9(6) . . . . ?
C10 N1 C11 C13 -0.1(6) . . . . ?
C10 N1 C11 C12 178.6(4) . . . . ?
C10 C9 C7 C8 113.0(4) . . . . ?
C10 C9 C7 C5 -65.9(6) . . . . ?
C5 C6 O3 Zn1 163.7(3) . . . 6_566 ?
C4 C5 C6 O4 -29.2(5) . . . . ?
C4 C5 C6 O3 152.0(4) . . . . ?
O4 C6 O3 Zn1 -15.0(5) . . . 6_566 ?
C6 C5 C4 C3 179.0(4) . . . . ?
O3 Zn1 O1 C1 51.8(3) 6_565 . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
loop_
_twin_individual_id
_twin_individual_mass_fraction_refined
1 0.8515(10)
2 0.1485(10)

####################################################################### 
# 
# 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_225_7zn
_database_code_depnum_ccdc_archive 'CCDC 1058046'
_audit_update_record             
;
2015-04-06 deposited with the CCDC.
2015-10-08 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C33 H33 N3 O20 Zn3'
_chemical_formula_weight         987.73

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Zn Zn 0.2839 1.4301 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_symmetry_cell_setting           Orthorhombic
_symmetry_space_group_name_H-M   Pbcn

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

_cell_length_a                   15.5051(7)
_cell_length_b                   12.2437(5)
_cell_length_c                   18.0992(5)
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_volume                     3436.0(2)
_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            colourless
_exptl_crystal_size_max          0.28
_exptl_crystal_size_mid          0.27
_exptl_crystal_size_min          0.18
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.909
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             2008
_exptl_absorpt_coefficient_mu    2.176
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.5810
_exptl_absorpt_correction_T_max  0.6955
_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  'Bruker APE-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            9140
_diffrn_reflns_av_R_equivalents  0.0486
_diffrn_reflns_av_sigmaI/netI    0.0553
_diffrn_reflns_limit_h_min       -18
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_theta_min         3.31
_diffrn_reflns_theta_max         25.05
_reflns_number_total             3029
_reflns_number_gt                2433
_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)+(0.0577P)²+11.0585P] 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         3029
_refine_ls_number_parameters     270
_refine_ls_number_restraints     18
_refine_ls_R_factor_all          0.0599
_refine_ls_R_factor_gt           0.0463
_refine_ls_wR_factor_ref         0.1274
_refine_ls_wR_factor_gt          0.1185
_refine_ls_goodness_of_fit_ref   1.058
_refine_ls_restrained_S_all      1.070
_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
Zn1 Zn 0.23714(4) 0.72258(5) 0.20767(3) 0.01129(19) Uani 1 1 d . . .
Zn2 Zn 0.5000 0.48251(7) 0.2500 0.0107(2) Uani 1 2 d S . .
N1 N 0.3116(3) 0.6607(3) 0.1228(2) 0.0115(9) Uani 1 1 d . . .
N2 N 0.5000 0.6502(5) 0.2500 0.0156(13) Uani 1 2 d S . .
O1 O 0.2990(2) 0.8644(3) 0.16804(18) 0.0144(8) Uani 1 1 d . . .
O2 O 0.3704(3) 0.9288(3) 0.0703(2) 0.0274(10) Uani 1 1 d . . .
O3 O 0.3799(2) 0.2947(3) 0.20145(17) 0.0139(8) Uani 1 1 d . . .
O4 O 0.4707(2) 0.4154(3) 0.15377(17) 0.0125(7) Uani 1 1 d . . .
O5 O 0.2446(3) 0.1415(3) -0.1497(2) 0.0280(10) Uani 1 1 d . . .
O6 O 0.2844(2) 0.3041(3) -0.19371(18) 0.0169(8) Uani 1 1 d . . .
O7 O 0.1634(3) 0.5750(3) 0.2187(2) 0.0248(9) Uani 1 1 d . . .
H1W H 0.1410 0.5719 0.2618 0.037 Uiso 1 1 d R . .
H2W H 0.1966 0.5200 0.2126 0.037 Uiso 1 1 d R . .
O8 O 0.3680(2) 0.4976(3) 0.28187(19) 0.0169(8) Uani 1 1 d . . .
H3W H 0.3595 0.5593 0.3032 0.025 Uiso 1 1 d R . .
H4W H 0.3550 0.4461 0.3121 0.025 Uiso 1 1 d R . .
O9 O 0.5323(6) 0.1277(7) 0.1917(4) 0.146(4) Uani 1 1 d G . .
H5W H 0.5570 0.1070 0.1651 0.219 Uiso 1 1 d G . .
H6W H 0.4802 0.1444 0.1825 0.219 Uiso 1 1 d G . .
O10 O 0.0293(6) 0.4655(7) 0.9483(4) 0.145(4) Uani 1 1 d G . .
H7W H 0.0781 0.4524 0.9262 0.218 Uiso 1 1 d G . .
H8W H -0.0159 0.4883 0.9266 0.218 Uiso 1 1 d G . .
C1 C 0.3393(3) 0.8534(4) 0.1066(3) 0.0150(11) Uani 1 1 d . . .
C2 C 0.3481(3) 0.7362(4) 0.0791(3) 0.0127(10) Uani 1 1 d . . .
C3 C 0.3900(3) 0.7090(4) 0.0149(3) 0.0169(11) Uani 1 1 d . . .
H3 H 0.4147 0.7630 -0.0144 0.020 Uiso 1 1 calc R . .
C4 C 0.3951(3) 0.6002(4) -0.0057(3) 0.0149(11) Uani 1 1 d . . .
H4 H 0.4222 0.5804 -0.0495 0.018 Uiso 1 1 calc R . .
C5 C 0.3591(3) 0.5209(4) 0.0399(3) 0.0110(10) Uani 1 1 d . . .
C6 C 0.3180(3) 0.5559(4) 0.1039(3) 0.0124(10) Uani 1 1 d . . .
H24 H 0.2939 0.5037 0.1349 0.015 Uiso 1 1 calc R . .
C7 C 0.3566(3) 0.4028(4) 0.0202(2) 0.0110(10) Uani 1 1 d . . .
C8 C 0.3784(3) 0.3205(4) 0.0710(3) 0.0116(10) Uani 1 1 d . . .
C9 C 0.4113(3) 0.3450(4) 0.1473(2) 0.0102(10) Uani 1 1 d . . .
C10 C 0.3700(3) 0.2110(4) 0.0508(3) 0.0113(10) Uani 1 1 d . . .
H10 H 0.3860 0.1565 0.0839 0.014 Uiso 1 1 calc R . .
C11 C 0.3382(3) 0.1828(4) -0.0181(3) 0.0138(11) Uani 1 1 d . . .
H11 H 0.3321 0.1096 -0.0307 0.017 Uiso 1 1 calc R . .
C12 C 0.3150(3) 0.2637(4) -0.0686(3) 0.0122(10) Uani 1 1 d . . .
C13 C 0.2781(3) 0.2320(4) -0.1423(3) 0.0149(11) Uani 1 1 d . . .
C14 C 0.3253(3) 0.3727(4) -0.0493(3) 0.0124(10) Uani 1 1 d . . .
H14 H 0.3111 0.4268 -0.0833 0.015 Uiso 1 1 calc R . .
C15 C 0.5152(4) 0.7074(5) 0.1880(3) 0.0276(14) Uani 1 1 d U . .
H15 H 0.5257 0.6696 0.1444 0.033 Uiso 1 1 calc R . .
C16 C 0.5159(4) 0.8200(6) 0.1866(5) 0.0448(19) Uani 1 1 d U . .
H16 H 0.5271 0.8571 0.1428 0.054 Uiso 1 1 calc R . .
C17 C 0.5000 0.8760(8) 0.2500 0.050(3) Uani 1 2 d SU . .
H17 H 0.5000 0.9520 0.2500 0.060 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
Zn1 O6 1.957(3) 8_566 ?
Zn1 O3 2.022(3) 7_665 ?
Zn1 N1 2.065(4) . ?
Zn1 O1 2.109(3) . ?
Zn1 O7 2.147(4) . ?
Zn2 O4 1.978(3) . ?
Zn2 O4 1.978(3) 4_655 ?
Zn2 N2 2.053(6) . ?
Zn2 O8 2.135(3) 4_655 ?
Zn2 O8 2.135(3) . ?
N1 C6 1.332(6) . ?
N1 C2 1.343(6) . ?
N2 C15 1.343(6) 4_655 ?
N2 C15 1.343(6) . ?
O1 C1 1.282(6) . ?
O2 C1 1.232(6) . ?
O3 C9 1.256(6) . ?
O3 Zn1 2.022(3) 7_655 ?
O4 C9 1.267(6) . ?
O5 C13 1.231(6) . ?
O6 C13 1.286(6) . ?
O6 Zn1 1.957(3) 8_565 ?
O7 H1W 0.8545 . ?
O7 H2W 0.8545 . ?
O8 H3W 0.8584 . ?
O8 H4W 0.8580 . ?
O9 H5W 0.6642 . ?
O9 H6W 0.8500 . ?
O10 H7W 0.8708 . ?
O10 H8W 0.8500 . ?
C1 C2 1.526(7) . ?
C2 C3 1.371(7) . ?
C3 C4 1.386(7) . ?
C3 H3 0.9300 . ?
C4 C5 1.391(7) . ?
C4 H4 0.9300 . ?
C5 C6 1.389(7) . ?
C5 C7 1.490(7) . ?
C6 H24 0.9300 . ?
C7 C14 1.398(6) . ?
C7 C8 1.405(7) . ?
C8 C10 1.395(7) . ?
C8 C9 1.503(6) . ?
C10 C11 1.385(7) . ?
C10 H10 0.9300 . ?
C11 C12 1.395(7) . ?
C11 H11 0.9300 . ?
C12 C14 1.389(7) . ?
C12 C13 1.503(7) . ?
C14 H14 0.9300 . ?
C15 C16 1.378(9) . ?
C15 H15 0.9300 . ?
C16 C17 1.359(9) . ?
C16 H16 0.9300 . ?
C17 C16 1.359(9) 4_655 ?
C17 H17 0.9300 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
O6 Zn1 O3 117.38(14) 8_566 7_665 ?
O6 Zn1 N1 114.05(15) 8_566 . ?
O3 Zn1 N1 128.38(14) 7_665 . ?
O6 Zn1 O1 106.13(14) 8_566 . ?
O3 Zn1 O1 91.71(13) 7_665 . ?
N1 Zn1 O1 78.16(14) . . ?
O6 Zn1 O7 88.47(15) 8_566 . ?
O3 Zn1 O7 83.96(14) 7_665 . ?
N1 Zn1 O7 93.34(15) . . ?
O1 Zn1 O7 165.10(14) . . ?
O4 Zn2 O4 131.0(2) . 4_655 ?
O4 Zn2 N2 114.52(10) . . ?
O4 Zn2 N2 114.52(10) 4_655 . ?
O4 Zn2 O8 91.04(13) . 4_655 ?
O4 Zn2 O8 93.07(13) 4_655 4_655 ?
N2 Zn2 O8 85.04(10) . 4_655 ?
O4 Zn2 O8 93.07(13) . . ?
O4 Zn2 O8 91.04(13) 4_655 . ?
N2 Zn2 O8 85.04(10) . . ?
O8 Zn2 O8 170.1(2) 4_655 . ?
C6 N1 C2 118.6(4) . . ?
C6 N1 Zn1 125.9(3) . . ?
C2 N1 Zn1 115.0(3) . . ?
C15 N2 C15 117.2(7) 4_655 . ?
C15 N2 Zn2 121.4(4) 4_655 . ?
C15 N2 Zn2 121.4(4) . . ?
C1 O1 Zn1 115.5(3) . . ?
C9 O3 Zn1 127.3(3) . 7_655 ?
C9 O4 Zn2 122.1(3) . . ?
C13 O6 Zn1 121.1(3) . 8_565 ?
Zn1 O7 H1W 109.9 . . ?
Zn1 O7 H2W 109.4 . . ?
H1W O7 H2W 109.1 . . ?
Zn2 O8 H3W 110.1 . . ?
Zn2 O8 H4W 109.5 . . ?
H3W O8 H4W 108.9 . . ?
H5W O9 H6W 119.7 . . ?
H7W O10 H8W 124.4 . . ?
O2 C1 O1 125.1(5) . . ?
O2 C1 C2 119.7(4) . . ?
O1 C1 C2 115.2(4) . . ?
N1 C2 C3 122.2(5) . . ?
N1 C2 C1 114.6(4) . . ?
C3 C2 C1 123.2(4) . . ?
C2 C3 C4 119.2(5) . . ?
C2 C3 H3 120.4 . . ?
C4 C3 H3 120.4 . . ?
C3 C4 C5 119.2(4) . . ?
C3 C4 H4 120.4 . . ?
C5 C4 H4 120.4 . . ?
C6 C5 C4 117.6(4) . . ?
C6 C5 C7 119.1(4) . . ?
C4 C5 C7 123.1(4) . . ?
N1 C6 C5 123.1(5) . . ?
N1 C6 H24 118.4 . . ?
C5 C6 H24 118.4 . . ?
C14 C7 C8 118.9(4) . . ?
C14 C7 C5 118.7(4) . . ?
C8 C7 C5 122.3(4) . . ?
C10 C8 C7 119.8(4) . . ?
C10 C8 C9 117.6(4) . . ?
C7 C8 C9 122.6(4) . . ?
O3 C9 O4 122.9(4) . . ?
O3 C9 C8 119.2(4) . . ?
O4 C9 C8 117.9(4) . . ?
C11 C10 C8 120.5(5) . . ?
C11 C10 H10 119.8 . . ?
C8 C10 H10 119.8 . . ?
C10 C11 C12 120.4(5) . . ?
C10 C11 H11 119.8 . . ?
C12 C11 H11 119.8 . . ?
C14 C12 C11 119.2(4) . . ?
C14 C12 C13 121.0(4) . . ?
C11 C12 C13 119.8(4) . . ?
O5 C13 O6 124.9(5) . . ?
O5 C13 C12 119.3(4) . . ?
O6 C13 C12 115.8(4) . . ?
C12 C14 C7 121.3(5) . . ?
C12 C14 H14 119.4 . . ?
C7 C14 H14 119.4 . . ?
N2 C15 C16 122.5(6) . . ?
N2 C15 H15 118.7 . . ?
C16 C15 H15 118.7 . . ?
C17 C16 C15 119.2(7) . . ?
C17 C16 H16 120.4 . . ?
C15 C16 H16 120.4 . . ?
C16 C17 C16 119.3(9) 4_655 . ?
C16 C17 H17 120.3 4_655 . ?
C16 C17 H17 120.3 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
O6 Zn1 N1 C6 74.9(4) 8_566 . . . ?
O3 Zn1 N1 C6 -99.9(4) 7_665 . . . ?
O1 Zn1 N1 C6 177.4(4) . . . . ?
O7 Zn1 N1 C6 -14.9(4) . . . . ?
O6 Zn1 N1 C2 -113.0(3) 8_566 . . . ?
O3 Zn1 N1 C2 72.2(4) 7_665 . . . ?
O1 Zn1 N1 C2 -10.5(3) . . . . ?
O7 Zn1 N1 C2 157.2(3) . . . . ?
O4 Zn2 N2 C15 153.5(3) . . . 4_655 ?
O4 Zn2 N2 C15 -26.5(3) 4_655 . . 4_655 ?
O8 Zn2 N2 C15 -117.6(3) 4_655 . . 4_655 ?
O8 Zn2 N2 C15 62.4(3) . . . 4_655 ?
O4 Zn2 N2 C15 -26.5(3) . . . . ?
O4 Zn2 N2 C15 153.5(3) 4_655 . . . ?
O8 Zn2 N2 C15 62.4(3) 4_655 . . . ?
O8 Zn2 N2 C15 -117.6(3) . . . . ?
O6 Zn1 O1 C1 122.9(3) 8_566 . . . ?
O3 Zn1 O1 C1 -117.9(3) 7_665 . . . ?
N1 Zn1 O1 C1 11.1(3) . . . . ?
O7 Zn1 O1 C1 -45.2(7) . . . . ?
O4 Zn2 O4 C9 53.4(3) 4_655 . . . ?
N2 Zn2 O4 C9 -126.6(3) . . . . ?
O8 Zn2 O4 C9 148.4(4) 4_655 . . . ?
O8 Zn2 O4 C9 -40.7(4) . . . . ?
Zn1 O1 C1 O2 170.9(4) . . . . ?
Zn1 O1 C1 C2 -9.6(5) . . . . ?
C6 N1 C2 C3 1.5(7) . . . . ?
Zn1 N1 C2 C3 -171.3(4) . . . . ?
C6 N1 C2 C1 -178.5(4) . . . . ?
Zn1 N1 C2 C1 8.8(5) . . . . ?
O2 C1 C2 N1 -179.9(5) . . . . ?
O1 C1 C2 N1 0.6(6) . . . . ?
O2 C1 C2 C3 0.2(8) . . . . ?
O1 C1 C2 C3 -179.3(5) . . . . ?
N1 C2 C3 C4 -0.1(8) . . . . ?
C1 C2 C3 C4 179.8(5) . . . . ?
C2 C3 C4 C5 -1.3(7) . . . . ?
C3 C4 C5 C6 1.2(7) . . . . ?
C3 C4 C5 C7 176.1(5) . . . . ?
C2 N1 C6 C5 -1.5(7) . . . . ?
Zn1 N1 C6 C5 170.4(4) . . . . ?
C4 C5 C6 N1 0.2(7) . . . . ?
C7 C5 C6 N1 -174.9(4) . . . . ?
C6 C5 C7 C14 124.9(5) . . . . ?
C4 C5 C7 C14 -49.9(7) . . . . ?
C6 C5 C7 C8 -50.2(7) . . . . ?
C4 C5 C7 C8 135.0(5) . . . . ?
C14 C7 C8 C10 1.1(7) . . . . ?
C5 C7 C8 C10 176.2(4) . . . . ?
C14 C7 C8 C9 -179.1(4) . . . . ?
C5 C7 C8 C9 -4.0(7) . . . . ?
Zn1 O3 C9 O4 157.2(3) 7_655 . . . ?
Zn1 O3 C9 C8 -23.7(6) 7_655 . . . ?
Zn2 O4 C9 O3 -16.4(6) . . . . ?
Zn2 O4 C9 C8 164.5(3) . . . . ?
C10 C8 C9 O3 -46.7(6) . . . . ?
C7 C8 C9 O3 133.5(5) . . . . ?
C10 C8 C9 O4 132.5(5) . . . . ?
C7 C8 C9 O4 -47.3(7) . . . . ?
C7 C8 C10 C11 -1.8(7) . . . . ?
C9 C8 C10 C11 178.4(4) . . . . ?
C8 C10 C11 C12 0.8(7) . . . . ?
C10 C11 C12 C14 0.7(7) . . . . ?
C10 C11 C12 C13 -178.2(5) . . . . ?
Zn1 O6 C13 O5 1.4(7) 8_565 . . . ?
Zn1 O6 C13 C12 -178.5(3) 8_565 . . . ?
C14 C12 C13 O5 -157.2(5) . . . . ?
C11 C12 C13 O5 21.8(7) . . . . ?
C14 C12 C13 O6 22.8(7) . . . . ?
C11 C12 C13 O6 -158.3(4) . . . . ?
C11 C12 C14 C7 -1.4(7) . . . . ?
C13 C12 C14 C7 177.6(5) . . . . ?
C8 C7 C14 C12 0.4(7) . . . . ?
C5 C7 C14 C12 -174.8(4) . . . . ?
C15 N2 C15 C16 0.3(4) 4_655 . . . ?
Zn2 N2 C15 C16 -179.7(4) . . . . ?
N2 C15 C16 C17 -0.5(8) . . . . ?
C15 C16 C17 C16 0.3(4) . . . 4_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
O7 H1W O9 0.85 2.00 2.679(9) 135.3 6_566
O7 H2W O1 0.85 2.07 2.799(5) 142.8 7_655
O8 H3W O6 0.86 2.04 2.787(5) 145.3 8_566
O8 H4W O5 0.86 2.00 2.735(5) 142.6 2
O9 H6W O3 0.85 2.43 3.130(9) 139.6 .
O9 H5W O10 0.66 2.28 2.779(14) 133.8 3_556
O10 H7W O9 0.87 2.45 2.779(13) 102.8 3_456

_diffrn_measured_fraction_theta_max 0.993
_diffrn_reflns_theta_full        25.05
_diffrn_measured_fraction_theta_full 0.993
_refine_diff_density_max         1.032
_refine_diff_density_min         -0.882
_refine_diff_density_rms         0.127
