# Supplementary Material (ESI) for Chemical Communications
# This journal is © The Royal Society of Chemistry 2005

data_cd(TTA)2xtmed
_database_code_depnum_ccdc_archive 'CCDC 277427'

_audit_creation_method           SHELXL-97
_chemical_name_systematic        ?
_chemical_name_common            Cd(tta)2tmed
_chemical_melting_point          155-158C
_chemical_formula_moiety         ?
_chemical_formula_sum            'C22 H24 Cd F6 N2 O4 S2'
_chemical_formula_weight         670.95

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 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'
F F 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
S S 0.1246 0.1234 '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           monoclinic
_symmetry_space_group_name_H-M   P21/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                   17.582(5)
_cell_length_b                   8.335(2)
_cell_length_c                   18.610(7)
_cell_angle_alpha                90.00
_cell_angle_beta                 92.61(3)
_cell_angle_gamma                90.00
_cell_volume                     2724.4(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       ?
_exptl_crystal_colour            ?
_exptl_crystal_size_max          0.60
_exptl_crystal_size_mid          0.55
_exptl_crystal_size_min          0.46
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.636
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1344
_exptl_absorpt_coefficient_mu    1.026
_exptl_absorpt_correction_type   'REFDELF (WALKER and STUART, 1983)'
_exptl_absorpt_correction_T_min  0.55
_exptl_absorpt_correction_T_max  0.62
_exptl_absorpt_process_details   ?

_exptl_special_details           
;
?
;

_diffrn_ambient_temperature      293(2)
_diffrn_radiation_wavelength     0.71069
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'X-ray tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Nonius CAD4'
_diffrn_measurement_method       \q/2\q
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            4804
_diffrn_reflns_av_R_equivalents  0.0327
_diffrn_reflns_av_sigmaI/netI    0.0127
_diffrn_reflns_limit_h_min       -20
_diffrn_reflns_limit_h_max       20
_diffrn_reflns_limit_k_min       0
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_l_min       0
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_theta_min         2.53
_diffrn_reflns_theta_max         24.97
_reflns_number_total             4640
_reflns_number_gt                4228
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'Nonius CAD4'
_computing_cell_refinement       'Nonius CAD4'
_computing_data_reduction        'Nonius CAD4'
_computing_structure_solution    'SIR97 (Altomare,1994)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    'ORTEP-3(Farrugia, 1997)'
_computing_publication_material  'PARST97 (Nardelli, 1997)'

_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^)+(0.0976P)^2^+4.1131P] 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    ?
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         4640
_refine_ls_number_parameters     339
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0553
_refine_ls_R_factor_gt           0.0510
_refine_ls_wR_factor_ref         0.1467
_refine_ls_wR_factor_gt          0.1413
_refine_ls_goodness_of_fit_ref   1.083
_refine_ls_restrained_S_all      1.083
_refine_ls_shift/su_max          0.026
_refine_ls_shift/su_mean         0.001

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
Cd1 Cd 0.755140(16) 0.11230(4) 0.115832(16) 0.03791(16) Uani 1 1 d . . .
F1 F 1.0063(3) -0.0168(9) 0.2069(3) 0.150(3) Uani 1 1 d . . .
F2 F 1.0440(2) -0.1372(9) 0.1173(2) 0.147(3) Uani 1 1 d . . .
F3 F 0.9853(3) -0.2464(9) 0.1954(4) 0.188(4) Uani 1 1 d . . .
F4 F 0.5969(2) -0.2461(5) 0.2574(2) 0.0899(12) Uani 1 1 d . . .
F5 F 0.4974(2) -0.1027(7) 0.2494(3) 0.125(2) Uani 1 1 d . . .
F6 F 0.5939(3) -0.0244(7) 0.3112(2) 0.1156(16) Uani 1 1 d . . .
S1 S 0.75060(10) -0.2110(2) -0.11491(8) 0.0766(5) Uani 1 1 d . . .
S2 S 0.54139(9) 0.3162(2) -0.04719(8) 0.0660(4) Uani 1 1 d . . .
O1 O 0.86616(18) -0.0052(4) 0.15688(16) 0.0509(8) Uani 1 1 d . . .
O2 O 0.77473(19) -0.0627(5) 0.02427(18) 0.0529(8) Uani 1 1 d . . .
O3 O 0.67667(17) -0.0231(4) 0.18677(17) 0.0506(8) Uani 1 1 d . . .
O4 O 0.64267(18) 0.1807(5) 0.06086(18) 0.0535(8) Uani 1 1 d . . .
N1 N 0.7631(2) 0.3266(5) 0.2015(2) 0.0540(10) Uani 1 1 d . . .
N2 N 0.8094(3) 0.3261(6) 0.0485(2) 0.0583(11) Uani 1 1 d . . .
C1 C 0.9115(2) -0.0817(5) 0.1194(2) 0.0421(10) Uani 1 1 d . . .
C2 C 0.9027(3) -0.1401(6) 0.0499(3) 0.0470(11) Uani 1 1 d . . .
H2 H 0.9445 -0.1893 0.0304 0.109(6) Uiso 1 1 calc R . .
C3 C 0.8351(3) -0.1306(5) 0.0067(2) 0.0409(10) Uani 1 1 d . . .
C4 C 0.9881(3) -0.1175(7) 0.1580(3) 0.0563(13) Uani 1 1 d . . .
C5 C 0.8332(3) -0.2105(5) -0.0645(2) 0.0450(10) Uani 1 1 d . . .
C6 C 0.6049(3) -0.0113(6) 0.1862(2) 0.0459(10) Uani 1 1 d . . .
C7 C 0.5556(3) 0.0636(6) 0.1387(3) 0.0479(10) Uani 1 1 d . . .
H7 H 0.5040 0.0575 0.1476 0.109(6) Uiso 1 1 calc R . .
C8 C 0.5761(2) 0.1507(5) 0.0765(2) 0.0416(9) Uani 1 1 d . . .
C9 C 0.5721(3) -0.0961(7) 0.2504(3) 0.0646(15) Uani 1 1 d . . .
C10 C 0.5153(3) 0.2113(5) 0.0271(3) 0.0465(10) Uani 1 1 d . . .
C11 C 0.8978(3) -0.3012(5) -0.0986(2) 0.0432(10) Uani 1 1 d . . .
H11 H 0.9475 -0.3186 -0.0809 0.109(6) Uiso 1 1 calc R . .
C12 C 0.8600(4) -0.3543(9) -0.1679(3) 0.0747(18) Uani 1 1 d . . .
H12 H 0.8864 -0.4127 -0.2013 0.109(6) Uiso 1 1 calc R . .
C13 C 0.7882(4) -0.3159(8) -0.1801(3) 0.0670(15) Uani 1 1 d . . .
H13 H 0.7607 -0.3452 -0.2220 0.109(6) Uiso 1 1 calc R . .
C14 C 0.4337(3) 0.1931(6) 0.0298(3) 0.0519(12) Uani 1 1 d . . .
H14 H 0.4080 0.1388 0.0650 0.109(6) Uiso 1 1 calc R . .
C15 C 0.3996(3) 0.2742(7) -0.0316(4) 0.0728(17) Uani 1 1 d . . .
H15 H 0.3472 0.2801 -0.0404 0.109(6) Uiso 1 1 calc R . .
C16 C 0.4503(4) 0.3422(8) -0.0764(4) 0.0700(16) Uani 1 1 d . . .
H16 H 0.4358 0.3969 -0.1184 0.109(6) Uiso 1 1 calc R . .
C17 C 0.6857(4) 0.3830(8) 0.2168(4) 0.083(2) Uani 1 1 d . . .
H17A H 0.6894 0.4731 0.2489 0.109(6) Uiso 1 1 calc R . .
H17B H 0.6582 0.2979 0.2388 0.109(6) Uiso 1 1 calc R . .
H17C H 0.6594 0.4145 0.1728 0.109(6) Uiso 1 1 calc R . .
C18 C 0.8014(4) 0.2771(9) 0.2696(4) 0.089(2) Uani 1 1 d . . .
H18A H 0.8535 0.2506 0.2616 0.109(6) Uiso 1 1 calc R . .
H18B H 0.7761 0.1850 0.2881 0.109(6) Uiso 1 1 calc R . .
H18C H 0.7997 0.3634 0.3036 0.109(6) Uiso 1 1 calc R . .
C19 C 0.8065(5) 0.4548(8) 0.1682(4) 0.096(2) Uani 1 1 d . . .
H19A H 0.7951 0.5556 0.1914 0.109(6) Uiso 1 1 calc R . .
H19B H 0.8604 0.4338 0.1770 0.109(6) Uiso 1 1 calc R . .
C20 C 0.7911(5) 0.4721(8) 0.0908(4) 0.088(2) Uani 1 1 d . . .
H20A H 0.8205 0.5616 0.0736 0.109(6) Uiso 1 1 calc R . .
H20B H 0.7376 0.4977 0.0821 0.109(6) Uiso 1 1 calc R . .
C21 C 0.8923(4) 0.3081(9) 0.0434(5) 0.090(2) Uani 1 1 d . . .
H21A H 0.9027 0.2214 0.0113 0.109(6) Uiso 1 1 calc R . .
H21B H 0.9150 0.2854 0.0902 0.109(6) Uiso 1 1 calc R . .
H21C H 0.9133 0.4056 0.0254 0.109(6) Uiso 1 1 calc R . .
C22 C 0.7740(5) 0.3364(10) -0.0239(4) 0.097(3) Uani 1 1 d . . .
H22A H 0.7982 0.4196 -0.0503 0.109(6) Uiso 1 1 calc R . .
H22B H 0.7209 0.3606 -0.0209 0.109(6) Uiso 1 1 calc R . .
H22C H 0.7797 0.2357 -0.0482 0.109(6) Uiso 1 1 calc R . .

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
Cd1 0.0370(2) 0.0371(2) 0.0396(2) 0.00092(11) 0.00230(14) 0.00208(11)
F1 0.080(3) 0.217(7) 0.149(5) -0.107(5) -0.054(3) 0.040(4)
F2 0.049(2) 0.317(9) 0.075(3) -0.025(4) -0.0010(19) 0.044(3)
F3 0.121(4) 0.187(6) 0.249(8) 0.146(6) -0.054(5) 0.015(4)
F4 0.098(3) 0.071(2) 0.103(3) 0.041(2) 0.024(2) 0.008(2)
F5 0.064(2) 0.174(5) 0.139(4) 0.091(4) 0.040(2) 0.013(3)
F6 0.169(5) 0.130(4) 0.051(2) -0.001(2) 0.033(2) -0.014(4)
S1 0.0878(11) 0.0786(11) 0.0621(10) -0.0103(7) -0.0117(8) 0.0018(8)
S2 0.0680(9) 0.0682(9) 0.0606(8) 0.0107(7) -0.0118(6) 0.0020(7)
O1 0.0512(18) 0.063(2) 0.0383(17) -0.0049(14) -0.0012(13) 0.0146(16)
O2 0.0488(18) 0.062(2) 0.0476(19) -0.0166(16) -0.0041(14) 0.0093(16)
O3 0.0428(17) 0.061(2) 0.0481(18) 0.0141(15) 0.0032(13) 0.0012(15)
O4 0.0411(17) 0.065(2) 0.0545(19) 0.0164(17) -0.0018(14) 0.0015(15)
N1 0.059(2) 0.043(2) 0.059(3) -0.0138(19) -0.0078(19) 0.0030(19)
N2 0.059(3) 0.053(3) 0.064(3) 0.017(2) 0.009(2) -0.005(2)
C1 0.040(2) 0.042(2) 0.044(2) 0.0030(19) 0.0007(18) 0.0029(18)
C2 0.046(2) 0.051(3) 0.043(3) -0.006(2) 0.0033(19) 0.004(2)
C3 0.046(2) 0.037(2) 0.039(2) -0.0029(17) 0.0059(18) -0.0027(18)
C4 0.050(3) 0.072(4) 0.045(3) -0.003(2) -0.005(2) 0.009(2)
C5 0.053(2) 0.044(2) 0.038(2) -0.0032(18) 0.0048(18) -0.007(2)
C6 0.047(2) 0.043(2) 0.048(3) 0.004(2) 0.0095(19) 0.0039(19)
C7 0.040(2) 0.049(2) 0.055(3) 0.006(2) 0.0040(19) 0.002(2)
C8 0.040(2) 0.036(2) 0.049(3) -0.0023(19) -0.0003(18) 0.0025(18)
C9 0.059(3) 0.068(4) 0.068(4) 0.020(3) 0.019(3) 0.004(3)
C10 0.050(2) 0.036(2) 0.053(3) -0.0019(19) -0.005(2) 0.0029(19)
C11 0.060(3) 0.046(2) 0.024(2) -0.0164(17) 0.0087(17) -0.016(2)
C12 0.086(5) 0.086(4) 0.054(3) -0.024(3) 0.020(3) -0.018(4)
C13 0.086(4) 0.069(4) 0.046(3) -0.005(3) -0.003(3) -0.015(3)
C14 0.044(2) 0.043(3) 0.067(3) -0.005(2) -0.016(2) 0.015(2)
C15 0.052(3) 0.063(4) 0.101(5) -0.005(3) -0.017(3) 0.005(3)
C16 0.075(4) 0.059(3) 0.073(4) -0.002(3) -0.029(3) 0.017(3)
C17 0.072(4) 0.074(4) 0.103(5) -0.039(4) -0.003(4) 0.023(3)
C18 0.098(5) 0.091(5) 0.077(4) -0.028(4) -0.022(4) 0.017(4)
C19 0.116(6) 0.055(4) 0.116(6) -0.029(4) 0.023(5) -0.033(4)
C20 0.107(5) 0.044(3) 0.114(6) 0.016(3) 0.018(4) -0.004(3)
C21 0.066(4) 0.084(5) 0.123(6) 0.036(4) 0.030(4) -0.004(3)
C22 0.108(6) 0.105(5) 0.078(5) 0.052(4) -0.003(4) -0.024(5)

_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 O3 2.255(3) . ?
Cd1 O4 2.258(3) . ?
Cd1 O2 2.281(3) . ?
Cd1 O1 2.284(3) . ?
Cd1 N1 2.393(4) . ?
Cd1 N2 2.401(4) . ?
F1 C4 1.267(7) . ?
F2 C4 1.279(7) . ?
F3 C4 1.282(8) . ?
F4 C9 1.328(7) . ?
F5 C9 1.313(7) . ?
F6 C9 1.321(8) . ?
S1 C13 1.658(6) . ?
S1 C5 1.693(5) . ?
S2 C16 1.682(6) . ?
S2 C10 1.717(5) . ?
O1 C1 1.257(5) . ?
O2 C3 1.259(6) . ?
O3 C6 1.266(6) . ?
O4 C8 1.245(5) . ?
N1 C19 1.467(8) . ?
N1 C18 1.467(8) . ?
N1 C17 1.480(8) . ?
N2 C22 1.461(8) . ?
N2 C21 1.473(7) . ?
N2 C20 1.493(9) . ?
C1 C2 1.383(7) . ?
C1 C4 1.526(7) . ?
C2 C3 1.407(7) . ?
C3 C5 1.482(6) . ?
C5 C11 1.526(6) . ?
C6 C7 1.361(6) . ?
C6 C9 1.524(7) . ?
C7 C8 1.426(7) . ?
C8 C10 1.468(6) . ?
C10 C14 1.444(7) . ?
C11 C12 1.492(7) . ?
C12 C13 1.312(10) . ?
C14 C15 1.436(8) . ?
C15 C16 1.369(10) . ?
C19 C20 1.461(11) . ?

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 Cd1 O4 81.09(12) . . ?
O3 Cd1 O2 103.56(14) . . ?
O4 Cd1 O2 88.97(13) . . ?
O3 Cd1 O1 97.23(12) . . ?
O4 Cd1 O1 167.77(13) . . ?
O2 Cd1 O1 79.61(12) . . ?
O3 Cd1 N1 90.14(15) . . ?
O4 Cd1 N1 97.86(14) . . ?
O2 Cd1 N1 165.53(15) . . ?
O1 Cd1 N1 94.25(13) . . ?
O3 Cd1 N2 160.94(15) . . ?
O4 Cd1 N2 86.37(14) . . ?
O2 Cd1 N2 90.43(16) . . ?
O1 Cd1 N2 97.98(14) . . ?
N1 Cd1 N2 77.36(17) . . ?
C13 S1 C5 92.7(3) . . ?
C16 S2 C10 92.3(3) . . ?
C1 O1 Cd1 125.9(3) . . ?
C3 O2 Cd1 129.7(3) . . ?
C6 O3 Cd1 126.4(3) . . ?
C8 O4 Cd1 131.1(3) . . ?
C19 N1 C18 110.0(6) . . ?
C19 N1 C17 110.5(5) . . ?
C18 N1 C17 108.2(5) . . ?
C19 N1 Cd1 106.2(4) . . ?
C18 N1 Cd1 112.1(4) . . ?
C17 N1 Cd1 109.8(3) . . ?
C22 N2 C21 109.2(6) . . ?
C22 N2 C20 110.2(6) . . ?
C21 N2 C20 110.8(6) . . ?
C22 N2 Cd1 111.2(4) . . ?
C21 N2 Cd1 112.1(4) . . ?
C20 N2 Cd1 103.2(3) . . ?
O1 C1 C2 130.6(4) . . ?
O1 C1 C4 113.9(4) . . ?
C2 C1 C4 115.5(4) . . ?
C1 C2 C3 124.7(4) . . ?
O2 C3 C2 125.3(4) . . ?
O2 C3 C5 116.7(4) . . ?
C2 C3 C5 118.0(4) . . ?
F1 C4 F2 109.5(6) . . ?
F1 C4 F3 100.4(6) . . ?
F2 C4 F3 105.3(6) . . ?
F1 C4 C1 113.4(5) . . ?
F2 C4 C1 115.5(4) . . ?
F3 C4 C1 111.4(5) . . ?
C3 C5 C11 127.4(4) . . ?
C3 C5 S1 118.7(4) . . ?
C11 C5 S1 113.9(3) . . ?
O3 C6 C7 130.3(4) . . ?
O3 C6 C9 111.7(4) . . ?
C7 C6 C9 118.0(4) . . ?
C6 C7 C8 125.7(4) . . ?
O4 C8 C7 124.6(4) . . ?
O4 C8 C10 116.8(4) . . ?
C7 C8 C10 118.7(4) . . ?
F5 C9 F6 106.3(6) . . ?
F5 C9 F4 106.6(5) . . ?
F6 C9 F4 105.1(5) . . ?
F5 C9 C6 115.0(5) . . ?
F6 C9 C6 110.9(5) . . ?
F4 C9 C6 112.3(5) . . ?
C14 C10 C8 129.6(4) . . ?
C14 C10 S2 112.6(4) . . ?
C8 C10 S2 117.8(4) . . ?
C12 C11 C5 101.2(4) . . ?
C13 C12 C11 117.7(5) . . ?
C12 C13 S1 114.5(5) . . ?
C15 C14 C10 107.6(5) . . ?
C16 C15 C14 114.8(5) . . ?
C15 C16 S2 112.7(5) . . ?
C20 C19 N1 114.3(6) . . ?
C19 C20 N2 113.8(6) . . ?

_diffrn_measured_fraction_theta_max 0.972
_diffrn_reflns_theta_full        24.97
_diffrn_measured_fraction_theta_full 0.972
_refine_diff_density_max         0.987
_refine_diff_density_min         -0.918
_refine_diff_density_rms         0.137