# Electronic Supplementary Material (ESI) for Inorganic Chemistry Frontiers.
# This journal is © the Partner Organisations 2014

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#
#                 Cambridge Crystallographic Data Centre
#                                CCDC 
# 
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# 
#  This CIF contains data from an original supplementary publication
#  deposited with the CCDC, and may include chemical, crystal,
#  experimental, refinement, atomic coordinates,
#  anisotropic displacement parameters and molecular geometry data,
#  as required by the journal to which it was submitted.
#
#  This CIF is provided on the understanding that it is used for bona
#  fide research purposes only. It may contain copyright material
#  of the CCDC or of third parties, and may not be copied or further
#  disseminated in any form, whether machine-readable or not,
#  except for the purpose of generating routine backup copies
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#  data retrieval see:
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#  Bona fide researchers may freely download Mercury and enCIFer
#  from this site to visualise CIF-encoded structures and 
#  to carry out CIF format checking respectively.
#
data_1

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C27 H26 Dy N9 O7'
_chemical_formula_weight         751.07

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'
Dy Dy -0.1892 4.4098 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_H-M   C2/c

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

_cell_length_a                   39.586(3)
_cell_length_b                   9.0348(5)
_cell_length_c                   18.2097(11)
_cell_angle_alpha                90.00
_cell_angle_beta                 116.851(4)
_cell_angle_gamma                90.00
_cell_volume                     5810.5(6)
_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          0.13
_exptl_crystal_size_mid          0.11
_exptl_crystal_size_min          0.10
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.717
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             2984
_exptl_absorpt_coefficient_mu    2.634
_exptl_absorpt_correction_type   empirical
_exptl_absorpt_correction_T_min  0.717
_exptl_absorpt_correction_T_max  0.767
_exptl_absorpt_process_details   SADABS

_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  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean 9.00cm
_diffrn_standards_number         none
_diffrn_standards_interval_count none
_diffrn_standards_interval_time  none
_diffrn_standards_decay_%        none
_diffrn_reflns_number            15947
_diffrn_reflns_av_R_equivalents  0.0429
_diffrn_reflns_av_sigmaI/netI    0.0370
_diffrn_reflns_limit_h_min       -47
_diffrn_reflns_limit_h_max       31
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_theta_min         1.15
_diffrn_reflns_theta_max         25.01
_reflns_number_total             5117
_reflns_number_gt                4402
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'Bruker SMAR'
_computing_cell_refinement       'Bruker SMAR'
_computing_data_reduction        'Bruker SMAR'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    ?
_computing_publication_material  ?

_refine_special_details          
; 
 Refinement of F² against ALL reflections.  The weighted R-factor wR and 
 goodness of fit S are based on F², conventional R-factors R are based 
 on F, with F set to zero for negative F². The threshold expression of 
 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is 
 not relevant to the choice of reflections for refinement.  R-factors based 
 on F² are statistically about twice as large as those based on F, and R- 
 factors based on ALL data will be even larger. 
;

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0535P)²+28.1176P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         5117
_refine_ls_number_parameters     397
_refine_ls_number_restraints     6
_refine_ls_R_factor_all          0.0462
_refine_ls_R_factor_gt           0.0386
_refine_ls_wR_factor_ref         0.1068
_refine_ls_wR_factor_gt          0.0978
_refine_ls_goodness_of_fit_ref   1.186
_refine_ls_restrained_S_all      1.185
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
Dy1 Dy 0.414390(7) 1.03731(3) 0.383752(14) 0.01680(11) Uani 1 1 d . . .
O1 O 0.35147(12) 1.0778(5) 0.3003(2) 0.0284(10) Uani 1 1 d . . .
O2 O 0.29078(19) 1.3426(13) 0.0057(4) 0.143(5) Uani 1 1 d . . .
O3 O 0.45315(12) 0.9956(5) 0.5269(2) 0.0267(9) Uani 1 1 d . . .
O4 O 0.40740(14) 1.0771(6) 0.7596(3) 0.0392(12) Uani 1 1 d . . .
O5 O 0.41400(13) 1.2721(4) 0.4317(3) 0.0337(10) Uani 1 1 d . . .
O6 O 0.45719(12) 1.8252(4) 0.4115(3) 0.0284(10) Uani 1 1 d . . .
OW1 O 0.47495(11) 1.1299(4) 0.4016(2) 0.0260(9) Uani 1 1 d . . .
N1 N 0.30057(15) 1.1304(7) 0.1804(3) 0.0417(15) Uani 1 1 d . . .
N2 N 0.28752(18) 1.2036(10) 0.1056(4) 0.076(3) Uani 1 1 d . . .
H2A H 0.2637 1.1947 0.0738 0.092 Uiso 1 1 calc R . .
N3 N 0.39880(15) 1.2308(6) 0.2587(3) 0.0332(13) Uani 1 1 d . . .
N4 N 0.46727(15) 1.0169(7) 0.6612(3) 0.0331(13) Uani 1 1 d . . .
N5 N 0.45297(16) 1.0377(7) 0.7176(3) 0.0360(14) Uani 1 1 d . . .
H5A H 0.4693 1.0333 0.7686 0.043 Uiso 1 1 calc R . .
N6 N 0.37885(14) 1.0447(6) 0.4764(3) 0.0253(11) Uani 1 1 d . . .
N7 N 0.45850(16) 1.4315(5) 0.4361(4) 0.0345(13) Uani 1 1 d . . .
N8 N 0.46689(16) 1.5780(5) 0.4261(4) 0.0333(13) Uani 1 1 d . . .
H8A H 0.4893 1.5934 0.4310 0.040 Uiso 1 1 calc R . .
N9 N 0.38191(14) 1.7806(5) 0.3706(3) 0.0229(11) Uani 1 1 d . . .
C1 C 0.4213(2) 1.3053(10) 0.2361(4) 0.056(2) Uani 1 1 d . . .
H1B H 0.4470 1.3056 0.2724 0.067 Uiso 1 1 calc R . .
C2 C 0.4098(3) 1.3839(15) 0.1623(6) 0.099(5) Uani 1 1 d D . .
C3 C 0.3709(3) 1.3736(15) 0.1072(6) 0.098(5) Uani 1 1 d . . .
H3A H 0.3616 1.4167 0.0553 0.118 Uiso 1 1 calc R . .
C4 C 0.3468(2) 1.2997(11) 0.1301(5) 0.060(3) Uani 1 1 d . . .
C5 C 0.36159(18) 1.2294(8) 0.2060(4) 0.0335(15) Uani 1 1 d . . .
C6 C 0.33664(17) 1.1426(7) 0.2296(4) 0.0286(14) Uani 1 1 d . . .
C7 C 0.3063(2) 1.2853(14) 0.0754(5) 0.084(4) Uani 1 1 d . . .
C8 C 0.4318(5) 1.5117(16) 0.1528(13) 0.231(15) Uani 1 1 d D . .
H8B H 0.4470 1.5639 0.2037 0.277 Uiso 1 1 calc R . .
H8C H 0.4166 1.5800 0.1092 0.277 Uiso 1 1 calc R . .
C9 C 0.4537(5) 1.4012(17) 0.1285(8) 0.158(9) Uani 1 1 d D . .
H9B H 0.4722 1.4524 0.1176 0.237 Uiso 1 1 calc R . .
H9C H 0.4366 1.3490 0.0800 0.237 Uiso 1 1 calc R . .
H9D H 0.4662 1.3320 0.1726 0.237 Uiso 1 1 calc R . .
C10 C 0.34284(18) 1.0723(8) 0.4538(4) 0.0344(16) Uani 1 1 d . . .
H10A H 0.3266 1.0739 0.3977 0.041 Uiso 1 1 calc R . .
C11 C 0.32694(15) 1.0997(10) 0.5081(4) 0.0431(18) Uani 1 1 d D . .
C12 C 0.35178(19) 1.0985(9) 0.5913(4) 0.0389(17) Uani 1 1 d . . .
H12A H 0.3430 1.1164 0.6300 0.047 Uiso 1 1 calc R . .
C13 C 0.38978(18) 1.0705(7) 0.6164(4) 0.0272(14) Uani 1 1 d . . .
C14 C 0.40288(17) 1.0456(7) 0.5580(3) 0.0240(13) Uani 1 1 d . . .
C15 C 0.44250(17) 1.0185(7) 0.5827(3) 0.0242(13) Uani 1 1 d . . .
C16 C 0.41714(19) 1.0638(7) 0.7031(4) 0.0296(15) Uani 1 1 d . . .
C17 C 0.28502(17) 1.1201(15) 0.4760(5) 0.084(4) Uani 1 1 d D . .
H17A H 0.2794 1.1339 0.5222 0.101 Uiso 1 1 calc R . .
H17B H 0.2723 1.0306 0.4475 0.101 Uiso 1 1 calc R . .
C18 C 0.2692(5) 1.2501(19) 0.4180(12) 0.202(10) Uani 1 1 d D . .
H18A H 0.2425 1.2570 0.3999 0.303 Uiso 1 1 calc R . .
H18B H 0.2740 1.2361 0.3712 0.303 Uiso 1 1 calc R . .
H18C H 0.2813 1.3396 0.4460 0.303 Uiso 1 1 calc R . .
C19 C 0.34560(18) 1.7511(7) 0.3492(4) 0.0304(14) Uani 1 1 d . . .
H19A H 0.3287 1.8300 0.3335 0.037 Uiso 1 1 calc R . .
C20 C 0.33124(14) 1.6092(8) 0.3488(4) 0.0345(15) Uani 1 1 d D . .
C21 C 0.35640(19) 1.4942(7) 0.3719(4) 0.0323(15) Uani 1 1 d . . .
H21A H 0.3481 1.3984 0.3731 0.039 Uiso 1 1 calc R . .
C22 C 0.39466(18) 1.5200(6) 0.3939(4) 0.0244(13) Uani 1 1 d . . .
C23 C 0.40549(17) 1.6655(6) 0.3905(3) 0.0232(13) Uani 1 1 d . . .
C24 C 0.44477(17) 1.6977(6) 0.4100(3) 0.0228(12) Uani 1 1 d . . .
C25 C 0.42356(18) 1.4036(7) 0.4216(4) 0.0302(14) Uani 1 1 d . . .
C26 C 0.28962(15) 1.5897(8) 0.3214(5) 0.050(2) Uani 1 1 d D . .
H26A H 0.2771 1.6835 0.3000 0.060 Uiso 1 1 calc R . .
H26B H 0.2859 1.5656 0.3692 0.060 Uiso 1 1 calc R . .
C27 C 0.2704(4) 1.4719(16) 0.2567(10) 0.153(8) Uani 1 1 d D . .
H27A H 0.2441 1.4672 0.2434 0.229 Uiso 1 1 calc R . .
H27B H 0.2821 1.3777 0.2775 0.229 Uiso 1 1 calc R . .
H27C H 0.2730 1.4960 0.2081 0.229 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
Dy1 O1 2.286(4) . ?
Dy1 O5 2.297(4) . ?
Dy1 O3 2.383(4) . ?
Dy1 O4 2.386(4) 6_575 ?
Dy1 OW1 2.418(4) . ?
Dy1 O6 2.455(4) 1_545 ?
Dy1 N9 2.610(5) 1_545 ?
Dy1 N6 2.640(5) . ?
Dy1 N3 2.712(5) . ?
O1 C6 1.289(7) . ?
O2 C7 1.246(9) . ?
O3 C15 1.280(7) . ?
O4 C16 1.257(7) . ?
O4 Dy1 2.386(4) 6_576 ?
O5 C25 1.285(8) . ?
O6 C24 1.248(7) . ?
O6 Dy1 2.455(4) 1_565 ?
N1 C6 1.303(8) . ?
N1 N2 1.388(8) . ?
N2 C7 1.328(11) . ?
N3 C1 1.321(9) . ?
N3 C5 1.347(8) . ?
N4 C15 1.319(8) . ?
N4 N5 1.391(7) . ?
N5 C16 1.341(9) . ?
N6 C10 1.317(8) . ?
N6 C14 1.356(7) . ?
N7 C25 1.310(9) . ?
N7 N8 1.396(7) . ?
N8 C24 1.338(8) . ?
N9 C23 1.333(7) . ?
N9 C19 1.336(8) . ?
N9 Dy1 2.610(5) 1_565 ?
C1 C2 1.402(11) . ?
C2 C3 1.411(12) . ?
C2 C8 1.5015(11) . ?
C3 C4 1.376(11) . ?
C4 C5 1.388(9) . ?
C4 C7 1.463(10) . ?
C5 C6 1.469(9) . ?
C8 C9 1.5135(10) . ?
C10 C11 1.412(9) . ?
C11 C12 1.384(9) . ?
C11 C17 1.5012(10) . ?
C12 C13 1.383(9) . ?
C13 C14 1.395(8) . ?
C13 C16 1.457(9) . ?
C14 C15 1.444(9) . ?
C17 C18 1.5136(10) . ?
C19 C20 1.401(9) . ?
C20 C21 1.367(9) . ?
C20 C26 1.5009(10) . ?
C21 C22 1.400(9) . ?
C22 C23 1.393(8) . ?
C22 C25 1.465(9) . ?
C23 C24 1.460(8) . ?
C26 C27 1.5138(10) . ?

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 Dy1 O5 84.99(16) . . ?
O1 Dy1 O3 136.25(14) . . ?
O5 Dy1 O3 80.89(15) . . ?
O1 Dy1 O4 79.29(16) . 6_575 ?
O5 Dy1 O4 137.96(17) . 6_575 ?
O3 Dy1 O4 135.23(16) . 6_575 ?
O1 Dy1 OW1 138.62(14) . . ?
O5 Dy1 OW1 78.80(15) . . ?
O3 Dy1 OW1 78.34(14) . . ?
O4 Dy1 OW1 87.77(15) 6_575 . ?
O1 Dy1 O6 134.84(15) . 1_545 ?
O5 Dy1 O6 139.95(15) . 1_545 ?
O3 Dy1 O6 66.92(14) . 1_545 ?
O4 Dy1 O6 68.31(16) 6_575 1_545 ?
OW1 Dy1 O6 72.07(14) . 1_545 ?
O1 Dy1 N9 74.78(15) . 1_545 ?
O5 Dy1 N9 140.20(16) . 1_545 ?
O3 Dy1 N9 90.42(15) . 1_545 ?
O4 Dy1 N9 71.71(16) 6_575 1_545 ?
OW1 Dy1 N9 137.47(14) . 1_545 ?
O6 Dy1 N9 65.83(14) 1_545 1_545 ?
O1 Dy1 N6 71.68(15) . . ?
O5 Dy1 N6 68.70(16) . . ?
O3 Dy1 N6 64.60(15) . . ?
O4 Dy1 N6 138.51(16) 6_575 . ?
OW1 Dy1 N6 133.40(14) . . ?
O6 Dy1 N6 113.95(15) 1_545 . ?
N9 Dy1 N6 72.48(15) 1_545 . ?
O1 Dy1 N3 64.68(15) . . ?
O5 Dy1 N3 71.69(16) . . ?
O3 Dy1 N3 144.13(16) . . ?
O4 Dy1 N3 66.33(17) 6_575 . ?
OW1 Dy1 N3 74.09(14) . . ?
O6 Dy1 N3 123.38(16) 1_545 . ?
N9 Dy1 N3 125.44(15) 1_545 . ?
N6 Dy1 N3 122.36(16) . . ?
C6 O1 Dy1 127.2(4) . . ?
C15 O3 Dy1 124.2(4) . . ?
C16 O4 Dy1 141.9(4) . 6_576 ?
C25 O5 Dy1 138.3(4) . . ?
C24 O6 Dy1 119.2(4) . 1_565 ?
C6 N1 N2 116.2(6) . . ?
C7 N2 N1 129.9(6) . . ?
C1 N3 C5 117.2(5) . . ?
C1 N3 Dy1 131.3(5) . . ?
C5 N3 Dy1 110.6(4) . . ?
C15 N4 N5 116.6(5) . . ?
C16 N5 N4 128.7(5) . . ?
C10 N6 C14 117.7(5) . . ?
C10 N6 Dy1 128.3(4) . . ?
C14 N6 Dy1 112.9(4) . . ?
C25 N7 N8 116.6(5) . . ?
C24 N8 N7 128.6(6) . . ?
C23 N9 C19 116.9(5) . . ?
C23 N9 Dy1 114.4(4) . 1_565 ?
C19 N9 Dy1 128.7(4) . 1_565 ?
N3 C1 C2 125.8(7) . . ?
C1 C2 C3 115.2(7) . . ?
C1 C2 C8 123.1(12) . . ?
C3 C2 C8 118.1(11) . . ?
C4 C3 C2 120.0(7) . . ?
C3 C4 C5 119.1(7) . . ?
C3 C4 C7 122.3(7) . . ?
C5 C4 C7 118.5(7) . . ?
N3 C5 C4 122.6(6) . . ?
N3 C5 C6 117.4(5) . . ?
C4 C5 C6 119.9(6) . . ?
O1 C6 N1 120.8(6) . . ?
O1 C6 C5 118.1(5) . . ?
N1 C6 C5 121.1(5) . . ?
O2 C7 N2 122.8(8) . . ?
O2 C7 C4 122.7(8) . . ?
N2 C7 C4 114.5(6) . . ?
C2 C8 C9 87.9(12) . . ?
N6 C10 C11 125.2(6) . . ?
C12 C11 C10 116.3(5) . . ?
C12 C11 C17 122.8(6) . . ?
C10 C11 C17 120.9(6) . . ?
C13 C12 C11 119.5(6) . . ?
C12 C13 C14 120.0(6) . . ?
C12 C13 C16 122.1(6) . . ?
C14 C13 C16 117.9(6) . . ?
N6 C14 C13 121.2(6) . . ?
N6 C14 C15 117.7(5) . . ?
C13 C14 C15 121.1(5) . . ?
O3 C15 N4 120.5(6) . . ?
O3 C15 C14 118.8(5) . . ?
N4 C15 C14 120.7(5) . . ?
O4 C16 N5 122.9(6) . . ?
O4 C16 C13 122.0(6) . . ?
N5 C16 C13 115.0(5) . . ?
C11 C17 C18 113.7(10) . . ?
N9 C19 C20 124.4(5) . . ?
C21 C20 C19 117.1(5) . . ?
C21 C20 C26 123.4(6) . . ?
C19 C20 C26 119.4(6) . . ?
C20 C21 C22 120.3(6) . . ?
C23 C22 C21 117.3(6) . . ?
C23 C22 C25 119.0(6) . . ?
C21 C22 C25 123.7(6) . . ?
N9 C23 C22 123.8(6) . . ?
N9 C23 C24 116.7(5) . . ?
C22 C23 C24 119.5(5) . . ?
O6 C24 N8 121.9(6) . . ?
O6 C24 C23 123.7(5) . . ?
N8 C24 C23 114.4(5) . . ?
O5 C25 N7 120.1(6) . . ?
O5 C25 C22 118.5(6) . . ?
N7 C25 C22 121.4(6) . . ?
C20 C26 C27 115.5(7) . . ?

_diffrn_measured_fraction_theta_max 0.999
_diffrn_reflns_theta_full        25.01
_diffrn_measured_fraction_theta_full 0.999
_refine_diff_density_max         1.286
_refine_diff_density_min         -1.264
_refine_diff_density_rms         0.241
_database_code_depnum_ccdc_archive 'CCDC 1015188'
#######################################################################
#
#                 Cambridge Crystallographic Data Centre
#                                CCDC 
# 
#######################################################################
# 
#  This CIF contains data from an original supplementary publication
#  deposited with the CCDC, and may include chemical, crystal,
#  experimental, refinement, atomic coordinates,
#  anisotropic displacement parameters and molecular geometry data,
#  as required by the journal to which it was submitted.
#
#  This CIF is provided on the understanding that it is used for bona
#  fide research purposes only. It may contain copyright material
#  of the CCDC or of third parties, and may not be copied or further
#  disseminated in any form, whether machine-readable or not,
#  except for the purpose of generating routine backup copies
#  on your local computer system.
# 
#  For further information on the CCDC, data deposition and
#  data retrieval see:
#                         www.ccdc.cam.ac.uk
#
#  Bona fide researchers may freely download Mercury and enCIFer
#  from this site to visualise CIF-encoded structures and 
#  to carry out CIF format checking respectively.
#
data_2

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C9 H6 Dy N3 O7'
_chemical_formula_weight         430.67

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'
Dy Dy -0.1892 4.4098 '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                   7.1376(4)
_cell_length_b                   7.8130(4)
_cell_length_c                   10.3661(7)
_cell_angle_alpha                90.681(4)
_cell_angle_beta                 103.088(4)
_cell_angle_gamma                101.710(3)
_cell_volume                     550.33(6)
_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       columnar
_exptl_crystal_colour            yellow
_exptl_crystal_size_max          0.11
_exptl_crystal_size_mid          0.11
_exptl_crystal_size_min          0.10
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    2.599
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             406
_exptl_absorpt_coefficient_mu    6.830
_exptl_absorpt_correction_type   empirical
_exptl_absorpt_correction_T_min  0.491
_exptl_absorpt_correction_T_max  0.505
_exptl_absorpt_process_details   SADABS

_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  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean 9.00cm
_diffrn_standards_number         none
_diffrn_standards_interval_count none
_diffrn_standards_interval_time  none
_diffrn_standards_decay_%        none
_diffrn_reflns_number            3129
_diffrn_reflns_av_R_equivalents  0.0247
_diffrn_reflns_av_sigmaI/netI    0.0189
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_limit_l_max       8
_diffrn_reflns_theta_min         2.02
_diffrn_reflns_theta_max         25.03
_reflns_number_total             1949
_reflns_number_gt                1917
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'Bruker SMAR'
_computing_cell_refinement       'Bruker SMAR'
_computing_data_reduction        'Bruker SMAR'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    ?
_computing_publication_material  ?

_refine_special_details          
; 
 Refinement of F² against ALL reflections.  The weighted R-factor wR and 
 goodness of fit S are based on F², conventional R-factors R are based 
 on F, with F set to zero for negative F². The threshold expression of 
 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is 
 not relevant to the choice of reflections for refinement.  R-factors based 
 on F² are statistically about twice as large as those based on F, and R- 
 factors based on ALL data will be even larger. 
;

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0370P)²+1.0215P] 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         1949
_refine_ls_number_parameters     189
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0215
_refine_ls_R_factor_gt           0.0211
_refine_ls_wR_factor_ref         0.0584
_refine_ls_wR_factor_gt          0.0582
_refine_ls_goodness_of_fit_ref   1.178
_refine_ls_restrained_S_all      1.178
_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
Dy1 Dy -0.71407(2) -1.20223(2) 0.926532(15) 0.01257(10) Uani 1 1 d . . .
N1 N -0.7295(5) -1.1698(5) 0.6776(3) 0.0185(7) Uani 1 1 d . . .
N2 N -0.5016(6) -0.7131(5) 0.7500(4) 0.0243(8) Uani 1 1 d . . .
N3 N -0.5509(6) -0.6564(5) 0.6238(4) 0.0270(9) Uani 1 1 d . . .
H3A H -0.5156 -0.5456 0.6164 0.032 Uiso 1 1 calc R . .
OW1 O -1.0263(5) -1.3849(5) 0.8103(4) 0.0263(7) Uani 1 1 d . . .
O1 O -0.5137(4) -0.9414(4) 0.8822(3) 0.0169(6) Uani 1 1 d . . .
O2 O -0.6753(6) -0.6816(5) 0.4016(3) 0.0358(9) Uani 1 1 d . . .
O3 O -0.9150(5) -1.0002(4) 0.8550(3) 0.0219(6) Uani 1 1 d . . .
O4 O -1.1007(5) -0.8327(4) 0.9199(3) 0.0209(6) Uani 1 1 d . . .
O5 O -0.7394(4) -1.4861(4) 1.0052(3) 0.0195(6) Uani 1 1 d . . .
O6 O -0.5636(5) -1.6824(4) 1.0880(3) 0.0223(7) Uani 1 1 d . . .
C1 C -0.8200(8) -1.2813(6) 0.5739(4) 0.0256(10) Uani 1 1 d . . .
H1A H -0.8609 -1.3985 0.5892 0.031 Uiso 1 1 calc R . .
C2 C -0.8569(8) -1.2314(7) 0.4426(5) 0.0311(11) Uani 1 1 d . . .
H2B H -0.9170 -1.3145 0.3727 0.037 Uiso 1 1 calc R . .
C3 C -0.8031(7) -1.0582(7) 0.4187(4) 0.0255(10) Uani 1 1 d . . .
H3B H -0.8283 -1.0212 0.3327 0.031 Uiso 1 1 calc R . .
C4 C -0.7099(6) -0.9386(6) 0.5263(4) 0.0204(9) Uani 1 1 d . . .
C5 C -0.6694(6) -1.0010(5) 0.6536(4) 0.0169(8) Uani 1 1 d . . .
C6 C -0.5582(6) -0.8796(6) 0.7650(4) 0.0165(8) Uani 1 1 d . . .
C7 C -0.6463(7) -0.7512(6) 0.5115(4) 0.0238(9) Uani 1 1 d . . .
C8 C -1.0055(6) -0.9508(6) 0.9352(4) 0.0169(8) Uani 1 1 d . . .
C9 C -0.5882(6) -1.5492(5) 1.0269(4) 0.0146(8) Uani 1 1 d . . .
H02 H -1.110(13) -1.357(11) 0.758(8) 0.06(2) Uiso 1 1 d . . .
H01 H -1.079(10) -1.449(9) 0.837(7) 0.03(2) Uiso 1 1 d . . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Dy1 O4 2.334(3) 2_337 ?
Dy1 O1 2.355(3) . ?
Dy1 O5 2.359(3) . ?
Dy1 O3 2.359(3) . ?
Dy1 O1 2.362(3) 2_437 ?
Dy1 O6 2.371(3) 2_427 ?
Dy1 OW1 2.430(4) . ?
Dy1 N1 2.575(3) . ?
Dy1 Dy1 3.9372(4) 2_437 ?
N1 C1 1.329(6) . ?
N1 C5 1.346(6) . ?
N2 C6 1.303(6) . ?
N2 N3 1.379(5) . ?
N3 C7 1.335(6) . ?
O1 C6 1.309(5) . ?
O1 Dy1 2.362(3) 2_437 ?
O2 C7 1.260(5) . ?
O3 C8 1.262(5) . ?
O4 C8 1.244(5) . ?
O4 Dy1 2.334(3) 2_337 ?
O5 C9 1.252(5) . ?
O6 C9 1.246(5) . ?
O6 Dy1 2.371(3) 2_427 ?
C1 C2 1.402(7) . ?
C2 C3 1.372(7) . ?
C3 C4 1.395(6) . ?
C4 C5 1.401(6) . ?
C4 C7 1.464(6) . ?
C5 C6 1.455(6) . ?
C8 C8 1.550(8) 2_337 ?
C9 C9 1.556(8) 2_427 ?

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
O4 Dy1 O1 114.60(11) 2_337 . ?
O4 Dy1 O5 82.74(11) 2_337 . ?
O1 Dy1 O5 148.74(10) . . ?
O4 Dy1 O3 69.61(10) 2_337 . ?
O1 Dy1 O3 71.55(11) . . ?
O5 Dy1 O3 139.56(11) . . ?
O4 Dy1 O1 74.17(11) 2_337 2_437 ?
O1 Dy1 O1 66.82(11) . 2_437 ?
O5 Dy1 O1 95.88(10) . 2_437 ?
O3 Dy1 O1 103.85(11) . 2_437 ?
O4 Dy1 O6 139.38(11) 2_337 2_427 ?
O1 Dy1 O6 82.14(11) . 2_427 ?
O5 Dy1 O6 68.94(10) . 2_427 ?
O3 Dy1 O6 148.60(11) . 2_427 ?
O1 Dy1 O6 80.26(11) 2_437 2_427 ?
O4 Dy1 OW1 81.36(12) 2_337 . ?
O1 Dy1 OW1 134.70(12) . . ?
O5 Dy1 OW1 70.93(12) . . ?
O3 Dy1 OW1 76.07(13) . . ?
O1 Dy1 OW1 153.59(12) 2_437 . ?
O6 Dy1 OW1 113.89(12) 2_427 . ?
O4 Dy1 N1 139.18(11) 2_337 . ?
O1 Dy1 N1 66.65(10) . . ?
O5 Dy1 N1 117.90(11) . . ?
O3 Dy1 N1 73.03(11) . . ?
O1 Dy1 N1 131.62(11) 2_437 . ?
O6 Dy1 N1 81.08(11) 2_427 . ?
OW1 Dy1 N1 74.20(13) . . ?
O4 Dy1 Dy1 94.89(8) 2_337 2_437 ?
O1 Dy1 Dy1 33.47(7) . 2_437 ?
O5 Dy1 Dy1 124.94(7) . 2_437 ?
O3 Dy1 Dy1 87.38(8) . 2_437 ?
O1 Dy1 Dy1 33.35(7) 2_437 2_437 ?
O6 Dy1 Dy1 79.44(8) 2_427 2_437 ?
OW1 Dy1 Dy1 163.33(10) . 2_437 ?
N1 Dy1 Dy1 99.29(8) . 2_437 ?
C1 N1 C5 117.6(4) . . ?
C1 N1 Dy1 130.2(3) . . ?
C5 N1 Dy1 110.6(3) . . ?
C6 N2 N3 117.2(4) . . ?
C7 N3 N2 128.4(4) . . ?
C6 O1 Dy1 118.5(2) . . ?
C6 O1 Dy1 127.3(2) . 2_437 ?
Dy1 O1 Dy1 113.18(11) . 2_437 ?
C8 O3 Dy1 117.8(3) . . ?
C8 O4 Dy1 118.0(3) . 2_337 ?
C9 O5 Dy1 117.7(3) . . ?
C9 O6 Dy1 117.6(3) . 2_427 ?
N1 C1 C2 123.4(4) . . ?
C3 C2 C1 119.0(4) . . ?
C2 C3 C4 118.5(4) . . ?
C3 C4 C5 118.8(4) . . ?
C3 C4 C7 122.8(4) . . ?
C5 C4 C7 118.4(4) . . ?
N1 C5 C4 122.6(4) . . ?
N1 C5 C6 118.3(4) . . ?
C4 C5 C6 119.1(4) . . ?
N2 C6 O1 120.0(4) . . ?
N2 C6 C5 121.6(4) . . ?
O1 C6 C5 118.4(4) . . ?
O2 C7 N3 121.3(4) . . ?
O2 C7 C4 123.5(4) . . ?
N3 C7 C4 115.1(4) . . ?
O4 C8 O3 126.4(4) . . ?
O4 C8 C8 117.9(5) . 2_337 ?
O3 C8 C8 115.6(5) . 2_337 ?
O6 C9 O5 126.7(4) . . ?
O6 C9 C9 116.5(4) . 2_427 ?
O5 C9 C9 116.8(4) . 2_427 ?

_diffrn_measured_fraction_theta_max 0.991
_diffrn_reflns_theta_full        25.03
_diffrn_measured_fraction_theta_full 0.991
_refine_diff_density_max         1.006
_refine_diff_density_min         -1.505
_refine_diff_density_rms         0.165
_database_code_depnum_ccdc_archive 'CCDC 1015189'
#######################################################################
#
#                 Cambridge Crystallographic Data Centre
#                                CCDC 
# 
#######################################################################
# 
#  This CIF contains data from an original supplementary publication
#  deposited with the CCDC, and may include chemical, crystal,
#  experimental, refinement, atomic coordinates,
#  anisotropic displacement parameters and molecular geometry data,
#  as required by the journal to which it was submitted.
#
#  This CIF is provided on the understanding that it is used for bona
#  fide research purposes only. It may contain copyright material
#  of the CCDC or of third parties, and may not be copied or further
#  disseminated in any form, whether machine-readable or not,
#  except for the purpose of generating routine backup copies
#  on your local computer system.
# 
#  For further information on the CCDC, data deposition and
#  data retrieval see:
#                         www.ccdc.cam.ac.uk
#
#  Bona fide researchers may freely download Mercury and enCIFer
#  from this site to visualise CIF-encoded structures and 
#  to carry out CIF format checking respectively.
#
data_3

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C11 H9 N12 O2 Zn2'
_chemical_formula_weight         472.04

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           monoclinic
_symmetry_space_group_name_H-M   C2/c

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

_cell_length_a                   12.3935(6)
_cell_length_b                   13.3918(7)
_cell_length_c                   10.3258(6)
_cell_angle_alpha                90.00
_cell_angle_beta                 117.390(3)
_cell_angle_gamma                90.00
_cell_volume                     1521.66(14)
_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            yellow
_exptl_crystal_size_max          0.12
_exptl_crystal_size_mid          0.10
_exptl_crystal_size_min          0.09
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    2.060
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             940
_exptl_absorpt_coefficient_mu    3.194
_exptl_absorpt_correction_type   empirical
_exptl_absorpt_correction_T_min  0.688
_exptl_absorpt_correction_T_max  0.750
_exptl_absorpt_process_details   SADABS

_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  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean 9.00cm
_diffrn_standards_number         none
_diffrn_standards_interval_count none
_diffrn_standards_interval_time  none
_diffrn_standards_decay_%        none
_diffrn_reflns_number            4199
_diffrn_reflns_av_R_equivalents  0.0276
_diffrn_reflns_av_sigmaI/netI    0.0241
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_limit_l_max       9
_diffrn_reflns_theta_min         2.40
_diffrn_reflns_theta_max         25.03
_reflns_number_total             1352
_reflns_number_gt                1178
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'Bruker SMAR'
_computing_cell_refinement       'Bruker SMAR'
_computing_data_reduction        'Bruker SMAR'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    ?
_computing_publication_material  ?

_refine_special_details          
; 
 Refinement of F² against ALL reflections.  The weighted R-factor wR and 
 goodness of fit S are based on F², conventional R-factors R are based 
 on F, with F set to zero for negative F². The threshold expression of 
 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is 
 not relevant to the choice of reflections for refinement.  R-factors based 
 on F² are statistically about twice as large as those based on F, and R- 
 factors based on ALL data will be even larger. 
;

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0271P)²+2.6228P] 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         1352
_refine_ls_number_parameters     139
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0259
_refine_ls_R_factor_gt           0.0214
_refine_ls_wR_factor_ref         0.0565
_refine_ls_wR_factor_gt          0.0547
_refine_ls_goodness_of_fit_ref   1.047
_refine_ls_restrained_S_all      1.047
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
Zn1 Zn 0.16564(3) 0.37671(2) 0.88703(3) 0.01748(11) Uani 1 1 d . . .
O1 O 0.17083(15) 0.18522(13) 1.03000(18) 0.0225(4) Uani 1 1 d . . .
N1 N 0.04863(18) 0.26232(15) 0.8208(2) 0.0175(4) Uani 1 1 d . . .
N2 N 0.1529(2) 0.55507(16) 1.2079(2) 0.0223(5) Uani 1 1 d . . .
N3 N 0.1406(2) 0.62097(16) 1.1007(2) 0.0282(5) Uani 1 1 d . . .
N4 N 0.1394(2) 0.57285(16) 0.9924(2) 0.0261(5) Uani 1 1 d . . .
N5 N 0.15149(19) 0.47264(15) 1.0243(2) 0.0210(5) Uani 1 1 d . . .
N6 N 0.1801(3) 0.3783(2) 1.2314(3) 0.0365(7) Uani 1 1 d . . .
C1 C 0.0870(2) 0.17829(19) 0.8953(3) 0.0193(5) Uani 1 1 d . . .
C2 C 0.0388(2) 0.08343(19) 0.8253(3) 0.0219(6) Uani 1 1 d . . .
C3 C 0.0738(3) -0.0078(2) 0.9001(3) 0.0290(7) Uani 1 1 d . . .
C4 C 0.0365(3) -0.0974(2) 0.8256(4) 0.0359(7) Uani 1 1 d . . .
C5 C 0.0761(5) -0.1951(4) 0.8922(7) 0.0363(15) Uani 0.50 1 d P . .
H5A H 0.0385 -0.2460 0.8198 0.080 Uiso 0.50 1 calc PR . .
H5B H 0.0531 -0.2036 0.9685 0.080 Uiso 0.50 1 calc PR . .
H5C H 0.1628 -0.2000 0.9323 0.080 Uiso 0.50 1 calc PR . .
C6 C 0.1605(2) 0.46422(19) 1.1578(3) 0.0204(5) Uani 1 1 d . . .
H2 H 0.123(2) -0.0092(19) 0.997(3) 0.016(7) Uiso 1 1 d . . .
H1 H 0.166(3) 0.377(2) 1.293(4) 0.022(9) Uiso 1 1 d . . .
H0 H 0.174(3) 0.328(2) 1.189(3) 0.027(9) Uiso 1 1 d . . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Zn1 N5 1.979(2) . ?
Zn1 O1 1.9828(17) 7_557 ?
Zn1 N1 2.001(2) . ?
Zn1 N2 2.003(2) 6_565 ?
O1 C1 1.301(3) . ?
O1 Zn1 1.9828(17) 7_557 ?
N1 C1 1.322(3) . ?
N1 N1 1.404(4) 2_556 ?
N2 C6 1.343(3) . ?
N2 N3 1.369(3) . ?
N2 Zn1 2.003(2) 6_566 ?
N3 N4 1.285(3) . ?
N4 N5 1.373(3) . ?
N5 C6 1.335(3) . ?
N6 C6 1.339(4) . ?
C1 C2 1.448(4) . ?
C2 C2 1.403(5) 2_556 ?
C2 C3 1.403(4) . ?
C3 C4 1.385(4) . ?
C4 C4 1.398(7) 2_556 ?
C4 C5 1.454(6) . ?

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
N5 Zn1 O1 111.82(8) . 7_557 ?
N5 Zn1 N1 116.90(9) . . ?
O1 Zn1 N1 105.27(8) 7_557 . ?
N5 Zn1 N2 111.70(9) . 6_565 ?
O1 Zn1 N2 102.75(8) 7_557 6_565 ?
N1 Zn1 N2 107.26(8) . 6_565 ?
C1 O1 Zn1 125.92(16) . 7_557 ?
C1 N1 N1 120.86(14) . 2_556 ?
C1 N1 Zn1 116.27(16) . . ?
N1 N1 Zn1 119.73(11) 2_556 . ?
C6 N2 N3 105.9(2) . . ?
C6 N2 Zn1 141.25(18) . 6_566 ?
N3 N2 Zn1 112.66(15) . 6_566 ?
N4 N3 N2 109.5(2) . . ?
N3 N4 N5 109.0(2) . . ?
C6 N5 N4 106.1(2) . . ?
C6 N5 Zn1 133.73(18) . . ?
N4 N5 Zn1 119.89(16) . . ?
O1 C1 N1 117.3(2) . . ?
O1 C1 C2 122.6(2) . . ?
N1 C1 C2 120.1(2) . . ?
C2 C2 C3 119.39(17) 2_556 . ?
C2 C2 C1 117.93(14) 2_556 . ?
C3 C2 C1 122.5(2) . . ?
C4 C3 C2 120.6(3) . . ?
C3 C4 C4 119.97(18) . 2_556 ?
C3 C4 C5 124.2(4) . . ?
C4 C4 C5 115.6(3) 2_556 . ?
N5 C6 N6 124.5(3) . . ?
N5 C6 N2 109.5(2) . . ?
N6 C6 N2 125.9(2) . . ?

_diffrn_measured_fraction_theta_max 0.999
_diffrn_reflns_theta_full        25.03
_diffrn_measured_fraction_theta_full 0.999
_refine_diff_density_max         0.357
_refine_diff_density_min         -0.251
_refine_diff_density_rms         0.065
_database_code_depnum_ccdc_archive 'CCDC 1015190'
#######################################################################
#
#                 Cambridge Crystallographic Data Centre
#                                CCDC 
# 
#######################################################################
# 
#  This CIF contains data from an original supplementary publication
#  deposited with the CCDC, and may include chemical, crystal,
#  experimental, refinement, atomic coordinates,
#  anisotropic displacement parameters and molecular geometry data,
#  as required by the journal to which it was submitted.
#
#  This CIF is provided on the understanding that it is used for bona
#  fide research purposes only. It may contain copyright material
#  of the CCDC or of third parties, and may not be copied or further
#  disseminated in any form, whether machine-readable or not,
#  except for the purpose of generating routine backup copies
#  on your local computer system.
# 
#  For further information on the CCDC, data deposition and
#  data retrieval see:
#                         www.ccdc.cam.ac.uk
#
#  Bona fide researchers may freely download Mercury and enCIFer
#  from this site to visualise CIF-encoded structures and 
#  to carry out CIF format checking respectively.
#
data_4

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C20 H16 N12 O6 Zn3'
_chemical_formula_weight         716.56

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           monoclinic
_symmetry_space_group_name_H-M   C2/c

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

_cell_length_a                   14.175(3)
_cell_length_b                   8.9672(18)
_cell_length_c                   20.104(4)
_cell_angle_alpha                90.00
_cell_angle_beta                 93.01(3)
_cell_angle_gamma                90.00
_cell_volume                     2552.0(9)
_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            yellow
_exptl_crystal_size_max          0.13
_exptl_crystal_size_mid          0.12
_exptl_crystal_size_min          0.10
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.865
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1432
_exptl_absorpt_coefficient_mu    2.861
_exptl_absorpt_correction_type   empirical
_exptl_absorpt_correction_T_min  0.696
_exptl_absorpt_correction_T_max  0.751
_exptl_absorpt_process_details   Process-auto

_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  'Rigaku RAXIS-RAPID'
_diffrn_measurement_method       omega-scan
_diffrn_detector_area_resol_mean 10.0
_diffrn_standards_number         0
_diffrn_standards_interval_count 0
_diffrn_standards_interval_time  0
_diffrn_standards_decay_%        0
_diffrn_reflns_number            12106
_diffrn_reflns_av_R_equivalents  0.0850
_diffrn_reflns_av_sigmaI/netI    0.0707
_diffrn_reflns_limit_h_min       -18
_diffrn_reflns_limit_h_max       18
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_l_min       -26
_diffrn_reflns_limit_l_max       25
_diffrn_reflns_theta_min         3.32
_diffrn_reflns_theta_max         27.47
_reflns_number_total             2907
_reflns_number_gt                2337
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       Process-auto
_computing_cell_refinement       Process-auto
_computing_data_reduction        Process-auto
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    ?
_computing_publication_material  ?

_refine_special_details          
; 
 Refinement of F² against ALL reflections.  The weighted R-factor wR and 
 goodness of fit S are based on F², conventional R-factors R are based 
 on F, with F set to zero for negative F². The threshold expression of 
 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is 
 not relevant to the choice of reflections for refinement.  R-factors based 
 on F² are statistically about twice as large as those based on F, and R- 
 factors based on ALL data will be even larger. 
;

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0669P)²+4.8389P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         2907
_refine_ls_number_parameters     186
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0634
_refine_ls_R_factor_gt           0.0499
_refine_ls_wR_factor_ref         0.1372
_refine_ls_wR_factor_gt          0.1266
_refine_ls_goodness_of_fit_ref   1.044
_refine_ls_restrained_S_all      1.044
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
Zn1 Zn 0.32457(3) 0.16066(5) 0.34051(2) 0.02735(18) Uani 1 1 d . . .
Zn2 Zn 0.5000 0.07142(7) 0.2500 0.0284(2) Uani 1 2 d S . .
N1 N 0.3079(3) 0.0789(4) 0.43063(17) 0.0351(8) Uani 1 1 d . . .
N2 N 0.3802(3) 0.0375(5) 0.47682(18) 0.0398(9) Uani 1 1 d . . .
N3 N 0.3029(2) 0.0040(4) 0.26864(16) 0.0280(7) Uani 1 1 d . . .
N4 N 0.3793(2) -0.0413(4) 0.23141(18) 0.0309(8) Uani 1 1 d . . .
N5 N 0.2527(2) -0.1679(4) 0.19478(17) 0.0292(7) Uani 1 1 d . . .
N6 N 0.1413(3) -0.0657(5) 0.2669(2) 0.0476(11) Uani 1 1 d . . .
H6A H 0.1299 -0.0045 0.2985 0.057 Uiso 1 1 calc R . .
H6B H 0.0966 -0.1202 0.2495 0.057 Uiso 1 1 calc R . .
O1 O 0.1556(2) 0.0745(4) 0.39712(17) 0.0457(8) Uani 1 1 d . . .
O2 O 0.4402(3) -0.0761(5) 0.56846(18) 0.0593(11) Uani 1 1 d . . .
OH1 O 0.4576(2) 0.1991(3) 0.32143(14) 0.0299(6) Uani 1 1 d . . .
C1 C 0.1076(4) -0.0876(7) 0.5127(3) 0.0560(15) Uani 1 1 d . . .
H1A H 0.0589 -0.0679 0.4811 0.067 Uiso 1 1 calc R . .
C2 C 0.0879(4) -0.1618(7) 0.5710(3) 0.0629(17) Uani 1 1 d . . .
H2B H 0.0262 -0.1882 0.5792 0.075 Uiso 1 1 calc R . .
C3 C 0.1617(4) -0.1964(6) 0.6169(3) 0.0514(13) Uani 1 1 d . . .
H3A H 0.1488 -0.2450 0.6563 0.062 Uiso 1 1 calc R . .
C4 C 0.2528(4) -0.1598(5) 0.6048(2) 0.0395(11) Uani 1 1 d . . .
H4A H 0.3018 -0.1871 0.6350 0.047 Uiso 1 1 calc R . .
C5 C 0.2724(3) -0.0811(5) 0.5470(2) 0.0333(9) Uani 1 1 d . . .
C6 C 0.1987(3) -0.0423(5) 0.5008(2) 0.0369(10) Uani 1 1 d . . .
C7 C 0.2191(3) 0.0409(5) 0.4400(2) 0.0376(10) Uani 1 1 d . . .
C8 C 0.3690(3) -0.0402(6) 0.5332(2) 0.0378(10) Uani 1 1 d . . .
C9 C 0.3456(3) -0.1414(5) 0.1891(2) 0.0327(9) Uani 1 1 d . . .
H9A H 0.3820 -0.1892 0.1584 0.039 Uiso 1 1 calc R . .
C10 C 0.2296(3) -0.0760(4) 0.2447(2) 0.0303(9) Uani 1 1 d . . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Zn1 OH1 1.974(3) . ?
Zn1 N1 1.980(3) . ?
Zn1 N5 1.996(3) 4 ?
Zn1 N3 2.027(3) . ?
Zn2 OH1 1.956(3) . ?
Zn2 OH1 1.956(3) 2_655 ?
Zn2 N4 2.005(3) . ?
Zn2 N4 2.005(3) 2_655 ?
N1 C7 1.326(6) . ?
N1 N2 1.397(5) . ?
N2 C8 1.348(6) . ?
N3 C10 1.332(5) . ?
N3 N4 1.408(5) . ?
N4 C9 1.309(5) . ?
N5 C9 1.349(5) . ?
N5 C10 1.352(5) . ?
N5 Zn1 1.996(3) 4_545 ?
N6 C10 1.354(6) . ?
O1 C7 1.250(5) . ?
O2 C8 1.244(6) . ?
C1 C6 1.387(7) . ?
C1 C2 1.389(8) . ?
C2 C3 1.394(8) . ?
C3 C4 1.366(7) . ?
C4 C5 1.401(6) . ?
C5 C6 1.403(6) . ?
C5 C8 1.459(6) . ?
C6 C7 1.474(6) . ?

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
OH1 Zn1 N1 113.82(14) . . ?
OH1 Zn1 N5 107.97(13) . 4 ?
N1 Zn1 N5 121.36(15) . 4 ?
OH1 Zn1 N3 95.34(13) . . ?
N1 Zn1 N3 111.99(15) . . ?
N5 Zn1 N3 102.74(14) 4 . ?
OH1 Zn2 OH1 108.33(17) . 2_655 ?
OH1 Zn2 N4 98.04(13) . . ?
OH1 Zn2 N4 116.77(13) 2_655 . ?
OH1 Zn2 N4 116.77(13) . 2_655 ?
OH1 Zn2 N4 98.04(13) 2_655 2_655 ?
N4 Zn2 N4 119.5(2) . 2_655 ?
C7 N1 N2 120.4(3) . . ?
C7 N1 Zn1 112.6(3) . . ?
N2 N1 Zn1 126.0(3) . . ?
C8 N2 N1 125.6(4) . . ?
C10 N3 N4 105.0(3) . . ?
C10 N3 Zn1 135.8(3) . . ?
N4 N3 Zn1 119.1(3) . . ?
C9 N4 N3 106.2(3) . . ?
C9 N4 Zn2 138.2(3) . . ?
N3 N4 Zn2 115.3(3) . . ?
C9 N5 C10 103.4(3) . . ?
C9 N5 Zn1 128.8(3) . 4_545 ?
C10 N5 Zn1 125.6(3) . 4_545 ?
Zn2 OH1 Zn1 111.96(14) . . ?
C6 C1 C2 121.1(5) . . ?
C1 C2 C3 119.3(5) . . ?
C4 C3 C2 120.8(5) . . ?
C3 C4 C5 119.9(5) . . ?
C4 C5 C6 120.1(4) . . ?
C4 C5 C8 120.8(4) . . ?
C6 C5 C8 119.1(4) . . ?
C1 C6 C5 118.7(4) . . ?
C1 C6 C7 121.0(4) . . ?
C5 C6 C7 120.2(4) . . ?
O1 C7 N1 119.6(4) . . ?
O1 C7 C6 121.9(4) . . ?
N1 C7 C6 118.4(4) . . ?
O2 C8 N2 119.1(4) . . ?
O2 C8 C5 124.7(4) . . ?
N2 C8 C5 116.2(4) . . ?
N4 C9 N5 113.0(4) . . ?
N3 C10 N5 112.4(4) . . ?
N3 C10 N6 124.1(4) . . ?
N5 C10 N6 123.5(4) . . ?

_diffrn_measured_fraction_theta_max 0.994
_diffrn_reflns_theta_full        27.47
_diffrn_measured_fraction_theta_full 0.994
_refine_diff_density_max         0.821
_refine_diff_density_min         -0.607
_refine_diff_density_rms         0.134
_database_code_depnum_ccdc_archive 'CCDC 1015191'
