# Supplementary Material (ESI) for Organic & Biomolecular Chemistry
# This journal is © The Royal Society of Chemistry 2005

data_global
_journal_name_full               Org.Biomol.Chem.

_journal_coden_Cambridge         0177

_publ_contact_author_name        'Dr. Claus Jacob'
_publ_contact_author_address     
; Exeter Biocatalysis Centre
School of Biological and Chemical Sciences
University of Exeter
Stocker Road
Exeter EX4 4QD
United Kingdom
;

_publ_contact_author_email       C.Jacob@ex.ac.uk
_publ_contact_author_phone       '+44 1392 263462'
_publ_contact_author_fax         '+44 1392 263434'
_publ_section_title              
;
Multifunctional Redox Catalysts as Selective Enhancers of Oxidative Stress
;
loop_
_publ_author_name
'Claus Jacob'
'Catriona Collins'
'Fiona H. Fry'
'Niroshini M. Giles'
'Gregory I. Giles'
'Nicholas J. Gutowski'
;
A.L.Holme
;
'Kim Holt'

data_s92
_database_code_depnum_ccdc_archive 'CCDC 269419'
_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C17 H12 O2 Te'
_chemical_formula_weight         375.87

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Te Te -0.5308 1.6751 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_H-M   P21/n

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

_cell_length_a                   11.8427(9)
_cell_length_b                   6.0131(3)
_cell_length_c                   20.0259(11)
_cell_angle_alpha                90.00
_cell_angle_beta                 90.914(5)
_cell_angle_gamma                90.00
_cell_volume                     1425.89(15)
_cell_formula_units_Z            4
_cell_measurement_temperature    120(2)
_cell_measurement_reflns_used    ?
_cell_measurement_theta_min      ?
_cell_measurement_theta_max      ?

_exptl_crystal_description       plate
_exptl_crystal_colour            red
_exptl_crystal_size_max          0.45
_exptl_crystal_size_mid          0.10
_exptl_crystal_size_min          0.05
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.751
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             728
_exptl_absorpt_coefficient_mu    2.084
_exptl_absorpt_correction_type   none
_exptl_special_details           
;
?
;

_diffrn_ambient_temperature      120(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'Nonius FR591 rotating anode'
_diffrn_measurement_device_type  'Nonius KappaCCD Area Detector'
_diffrn_measurement_method       '\f and \w scans to fill Ewald sphere'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            9936
_diffrn_reflns_av_R_equivalents  0.0462
_diffrn_reflns_av_sigmaI/netI    0.0463
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_k_min       -6
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_l_min       -24
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_theta_min         3.44
_diffrn_reflns_theta_max         25.99
_reflns_number_total             2793
_reflns_number_gt                2374
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       
'DENZO (Otwinowski & Minor, 1997) and COLLECT (Hooft, 1998)'
_computing_cell_refinement       'DENZO and COLLECT'
_computing_data_reduction        'DENZO and COLLECT'
_computing_structure_solution    'SHELXS97 (Sheldrick, 1997)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 1997)'
_computing_molecular_graphics    'PLATON (Spek, 1990)'

_refine_special_details          
;
Refinement of F^2^ against ALL reflections. The weighted R-factor wR and
goodness of fit S are based on F^2^, conventional R-factors R are based
on F, with F set to zero for negative F^2^. The threshold expression of
F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is
not relevant to the choice of reflections for refinement. R-factors based
on F^2^ 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/[\s^2^(Fo^2^)+(0.0485P)^2^+0.5286P] where P=(Fo^2^+2Fc^2^)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     SHELXL
_refine_ls_extinction_coef       0.0024(6)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^
_refine_ls_number_reflns         2793
_refine_ls_number_parameters     192
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0424
_refine_ls_R_factor_gt           0.0327
_refine_ls_wR_factor_ref         0.0849
_refine_ls_wR_factor_gt          0.0804
_refine_ls_goodness_of_fit_ref   1.019
_refine_ls_restrained_S_all      1.019
_refine_ls_shift/su_max          0.004
_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
Te1 Te 0.255032(17) 0.95050(4) 0.179284(11) 0.02421(13) Uani 1 1 d . . .
O1 O 0.46013(19) 0.7276(5) 0.24148(12) 0.0291(6) Uani 1 1 d . . .
O2 O 0.3997(2) 0.2972(5) 0.01023(13) 0.0395(7) Uani 1 1 d . . .
C1 C 0.0981(3) 0.8465(7) 0.13699(16) 0.0240(7) Uani 1 1 d . . .
C2 C 0.0338(3) 1.0015(7) 0.1007(2) 0.0326(9) Uani 1 1 d . . .
H2 H 0.0621 1.1466 0.0925 0.035(11) Uiso 1 1 calc R . .
C3 C -0.0721(4) 0.9391(8) 0.0768(2) 0.0410(11) Uani 1 1 d . . .
H3 H -0.1166 1.0436 0.0524 0.050(14) Uiso 1 1 calc R . .
C4 C -0.1141(3) 0.7298(8) 0.0877(2) 0.0410(10) Uani 1 1 d . . .
H4 H -0.1866 0.6901 0.0706 0.050(13) Uiso 1 1 calc R . .
C5 C -0.0500(3) 0.5755(7) 0.1238(2) 0.0390(10) Uani 1 1 d . . .
H5 H -0.0786 0.4300 0.1311 0.047(14) Uiso 1 1 calc R . .
C6 C 0.0559(3) 0.6352(7) 0.14907(18) 0.0299(8) Uani 1 1 d . . .
H6 H 0.0992 0.5315 0.1745 0.036(12) Uiso 1 1 calc R . .
C7 C 0.3529(3) 0.6850(6) 0.14151(16) 0.0223(7) Uani 1 1 d . . .
C8 C 0.4429(3) 0.6188(6) 0.19061(17) 0.0236(7) Uani 1 1 d . . .
C9 C 0.5112(3) 0.4201(6) 0.17510(18) 0.0245(8) Uani 1 1 d . . .
C10 C 0.5905(3) 0.3436(8) 0.22213(19) 0.0314(9) Uani 1 1 d . . .
H10 H 0.6024 0.4223 0.2628 0.040(13) Uiso 1 1 calc R . .
C11 C 0.6519(3) 0.1518(8) 0.2092(2) 0.0408(10) Uani 1 1 d . . .
H11 H 0.7055 0.0988 0.2412 0.040(12) Uiso 1 1 calc R . .
C12 C 0.6348(4) 0.0371(8) 0.1494(2) 0.0417(11) Uani 1 1 d . . .
H12 H 0.6767 -0.0943 0.1409 0.062(16) Uiso 1 1 calc R . .
C13 C 0.5570(3) 0.1136(7) 0.1023(2) 0.0334(9) Uani 1 1 d . . .
H13 H 0.5461 0.0354 0.0615 0.047(14) Uiso 1 1 calc R . .
C14 C 0.4950(3) 0.3050(6) 0.11492(17) 0.0263(8) Uani 1 1 d . . .
C15 C 0.4125(3) 0.3905(7) 0.06447(18) 0.0284(8) Uani 1 1 d . . .
C16 C 0.3430(3) 0.5909(6) 0.08062(18) 0.0260(8) Uani 1 1 d . . .
C17 C 0.2663(3) 0.6759(7) 0.02608(17) 0.0316(9) Uani 1 1 d . . .
H17A H 0.2736 0.5817 -0.0136 0.047 Uiso 0.51(5) 1 calc PR . .
H17B H 0.2872 0.8290 0.0150 0.047 Uiso 0.51(5) 1 calc PR . .
H17C H 0.1880 0.6724 0.0412 0.047 Uiso 0.51(5) 1 calc PR . .
H17D H 0.2256 0.8070 0.0420 0.047 Uiso 0.49(5) 1 calc PR . .
H17E H 0.2120 0.5597 0.0134 0.047 Uiso 0.49(5) 1 calc PR . .
H17F H 0.3112 0.7164 -0.0128 0.047 Uiso 0.49(5) 1 calc PR . .

loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_23
_atom_site_aniso_U_13
_atom_site_aniso_U_12
Te1 0.02573(18) 0.02185(18) 0.02514(18) -0.00288(9) 0.00283(10) 0.00101(9)
O1 0.0304(13) 0.0319(15) 0.0249(13) -0.0053(12) -0.0023(10) -0.0002(12)
O2 0.0525(16) 0.0393(18) 0.0270(14) -0.0118(13) 0.0059(11) 0.0026(14)
C1 0.0239(17) 0.029(2) 0.0195(17) -0.0001(16) 0.0034(12) 0.0033(15)
C2 0.033(2) 0.033(2) 0.031(2) 0.0020(17) 0.0015(16) 0.0080(17)
C3 0.037(2) 0.050(3) 0.036(2) -0.008(2) -0.0064(18) 0.020(2)
C4 0.0274(19) 0.052(3) 0.043(2) -0.023(2) -0.0017(16) 0.007(2)
C5 0.030(2) 0.038(3) 0.050(3) -0.014(2) 0.0085(18) -0.0023(17)
C6 0.0304(19) 0.028(2) 0.031(2) -0.0010(18) 0.0049(15) 0.0038(17)
C7 0.0186(15) 0.026(2) 0.0220(17) -0.0014(15) 0.0058(12) -0.0006(14)
C8 0.0219(16) 0.0212(18) 0.0277(19) 0.0013(16) 0.0049(13) -0.0020(14)
C9 0.0198(17) 0.025(2) 0.0293(19) 0.0009(15) 0.0067(14) -0.0047(14)
C10 0.0216(17) 0.038(2) 0.035(2) 0.0045(19) 0.0047(14) 0.0023(17)
C11 0.0242(19) 0.045(3) 0.053(3) 0.009(2) 0.0061(17) 0.0073(19)
C12 0.032(2) 0.040(3) 0.054(3) 0.002(2) 0.019(2) 0.0128(19)
C13 0.034(2) 0.026(2) 0.041(2) -0.0042(18) 0.0173(17) -0.0015(17)
C14 0.0245(17) 0.027(2) 0.0279(19) -0.0010(15) 0.0108(13) -0.0018(14)
C15 0.0263(18) 0.029(2) 0.030(2) -0.0021(17) 0.0081(15) -0.0032(16)
C16 0.0272(18) 0.028(2) 0.0234(18) -0.0029(15) 0.0063(14) -0.0015(15)
C17 0.0329(19) 0.044(3) 0.0182(17) 0.0012(17) 0.0034(14) 0.0022(17)

_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
Te1 C7 2.119(3) . ?
Te1 C1 2.124(3) . ?
O1 C8 1.225(4) . ?
O2 C15 1.230(5) . ?
C1 C6 1.388(6) . ?
C1 C2 1.400(5) . ?
C2 C3 1.387(6) . ?
C2 H2 0.9500 . ?
C3 C4 1.372(7) . ?
C3 H3 0.9500 . ?
C4 C5 1.393(6) . ?
C4 H4 0.9500 . ?
C5 C6 1.393(6) . ?
C5 H5 0.9500 . ?
C6 H6 0.9500 . ?
C7 C16 1.348(5) . ?
C7 C8 1.493(5) . ?
C8 C9 1.478(5) . ?
C9 C10 1.397(5) . ?
C9 C14 1.401(5) . ?
C10 C11 1.390(6) . ?
C10 H10 0.9500 . ?
C11 C12 1.393(7) . ?
C11 H11 0.9500 . ?
C12 C13 1.387(7) . ?
C12 H12 0.9500 . ?
C13 C14 1.390(5) . ?
C13 H13 0.9500 . ?
C14 C15 1.486(5) . ?
C15 C16 1.497(5) . ?
C16 C17 1.499(5) . ?
C17 H17A 0.9800 . ?
C17 H17B 0.9800 . ?
C17 H17C 0.9800 . ?
C17 H17D 0.9800 . ?
C17 H17E 0.9800 . ?
C17 H17F 0.9800 . ?

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
C7 Te1 C1 96.64(13) . . ?
C6 C1 C2 120.3(3) . . ?
C6 C1 Te1 121.0(3) . . ?
C2 C1 Te1 118.5(3) . . ?
C3 C2 C1 118.7(4) . . ?
C3 C2 H2 120.6 . . ?
C1 C2 H2 120.6 . . ?
C4 C3 C2 121.4(4) . . ?
C4 C3 H3 119.3 . . ?
C2 C3 H3 119.3 . . ?
C3 C4 C5 119.9(4) . . ?
C3 C4 H4 120.1 . . ?
C5 C4 H4 120.1 . . ?
C6 C5 C4 119.8(4) . . ?
C6 C5 H5 120.1 . . ?
C4 C5 H5 120.1 . . ?
C1 C6 C5 119.8(4) . . ?
C1 C6 H6 120.1 . . ?
C5 C6 H6 120.1 . . ?
C16 C7 C8 122.3(3) . . ?
C16 C7 Te1 126.8(3) . . ?
C8 C7 Te1 110.8(2) . . ?
O1 C8 C9 121.5(3) . . ?
O1 C8 C7 120.9(3) . . ?
C9 C8 C7 117.7(3) . . ?
C10 C9 C14 119.9(3) . . ?
C10 C9 C8 119.2(3) . . ?
C14 C9 C8 120.8(3) . . ?
C11 C10 C9 119.7(4) . . ?
C11 C10 H10 120.1 . . ?
C9 C10 H10 120.1 . . ?
C10 C11 C12 120.1(4) . . ?
C10 C11 H11 119.9 . . ?
C12 C11 H11 119.9 . . ?
C13 C12 C11 120.4(4) . . ?
C13 C12 H12 119.8 . . ?
C11 C12 H12 119.8 . . ?
C12 C13 C14 119.9(4) . . ?
C12 C13 H13 120.1 . . ?
C14 C13 H13 120.1 . . ?
C13 C14 C9 120.0(4) . . ?
C13 C14 C15 120.4(3) . . ?
C9 C14 C15 119.6(3) . . ?
O2 C15 C14 120.9(4) . . ?
O2 C15 C16 119.8(3) . . ?
C14 C15 C16 119.3(3) . . ?
C7 C16 C15 119.6(3) . . ?
C7 C16 C17 124.0(3) . . ?
C15 C16 C17 116.5(3) . . ?
C16 C17 H17A 109.5 . . ?
C16 C17 H17B 109.5 . . ?
H17A C17 H17B 109.5 . . ?
C16 C17 H17C 109.5 . . ?
H17A C17 H17C 109.5 . . ?
H17B C17 H17C 109.5 . . ?
C16 C17 H17D 109.5 . . ?
H17A C17 H17D 141.1 . . ?
H17B C17 H17D 56.3 . . ?
H17C C17 H17D 56.3 . . ?
C16 C17 H17E 109.5 . . ?
H17A C17 H17E 56.3 . . ?
H17B C17 H17E 141.1 . . ?
H17C C17 H17E 56.3 . . ?
H17D C17 H17E 109.5 . . ?
C16 C17 H17F 109.5 . . ?
H17A C17 H17F 56.3 . . ?
H17B C17 H17F 56.3 . . ?
H17C C17 H17F 141.1 . . ?
H17D C17 H17F 109.5 . . ?
H17E C17 H17F 109.5 . . ?

_diffrn_measured_fraction_theta_max 0.993
_diffrn_reflns_theta_full        25.99
_diffrn_measured_fraction_theta_full 0.993
_refine_diff_density_max         1.554
_refine_diff_density_min         -0.823
_refine_diff_density_rms         0.113