# Supplementary Material (ESI) for Perkin Transactions
# This journal is © The Royal Society of Chemistry 2000
# CCDC Number: 207/421
 
data_sl9906 
 
_audit_creation_method            SHELXL 
_chemical_name_systematic 
; 
 ? 
; 
_chemical_name_common             ? 
_chemical_formula_moiety          ? 
_chemical_formula_structural      ? 
_chemical_formula_analytical      ? 
_chemical_formula_sum             'C19.50 H18 Cl Fe N O9' 
_chemical_formula_weight          501.65 
_chemical_melting_point           ? 
_chemical_compound_source         ? 
 
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' 
 'Fe'  'Fe'   0.3463   0.8444 
 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 
 'Cl'  'Cl'   0.1484   0.1585 
 '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                    11.432(8) 
_cell_length_b                    24.740(12) 
_cell_length_c                    7.678(4) 
_cell_angle_alpha                 90.00 
_cell_angle_beta                  92.45(5) 
_cell_angle_gamma                 90.00 
_cell_volume                      2169.6(22) 
_cell_formula_units_Z             4 
_cell_measurement_temperature     220(2) 
_cell_measurement_reflns_used     ? 
_cell_measurement_theta_min       ? 
_cell_measurement_theta_max       ? 
 
_exptl_crystal_description        ? 
_exptl_crystal_colour             colourless 
_exptl_crystal_size_max           0.28 
_exptl_crystal_size_mid           0.25 
_exptl_crystal_size_min           0.20 
_exptl_crystal_density_meas       ? 
_exptl_crystal_density_diffrn     1.536 
_exptl_crystal_density_method     ? 
_exptl_crystal_F_000              1028 
_exptl_absorpt_coefficient_mu     0.869 
_exptl_absorpt_correction_type    ? 
_exptl_absorpt_correction_T_min   ? 
_exptl_absorpt_correction_T_max   ? 
 
_exptl_special_details 
; 
 ? 
; 
 
_diffrn_ambient_temperature       220(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        RAXIS-IIC 
_diffrn_measurement_method        ? 
_diffrn_standards_number          ? 
_diffrn_standards_interval_count  ? 
_diffrn_standards_interval_time   ? 
_diffrn_standards_decay_%         ? 
_diffrn_reflns_number             7141 
_diffrn_reflns_av_R_equivalents   0.0492 
_diffrn_reflns_av_sigmaI/netI     0.1349 
_diffrn_reflns_limit_h_min        0 
_diffrn_reflns_limit_h_max        13 
_diffrn_reflns_limit_k_min        0 
_diffrn_reflns_limit_k_max        29 
_diffrn_reflns_limit_l_min        -9 
_diffrn_reflns_limit_l_max        9 
_diffrn_reflns_theta_min          1.78 
_diffrn_reflns_theta_max          25.20 
_reflns_number_total              3827 
_reflns_number_observed           2598 
_reflns_observed_criterion        >2sigma(I) 
 
_computing_data_collection        ? 
_computing_cell_refinement        ? 
_computing_data_reduction         ? 
_computing_structure_solution     'teXsan' 
_computing_structure_refinement   'SHELXL-93 (Sheldrick, 1993)' 
_computing_molecular_graphics     ? 
_computing_publication_material   ? 
 
_refine_special_details 
; 
 Refinement on F^2^ for ALL reflections except for 0 with very negative F^2^ 
 or flagged by the user for potential systematic errors.  Weighted R-factors 
 wR and all goodnesses 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 observed criterion 
 of F^2^ > 2sigma(F^2^) is used only for calculating _R_factor_obs 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 w=1/[\s^2^(Fo^2^)+(0.0316P)^2^+0.0000P] 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      SHELXL 
_refine_ls_extinction_coef        0.0460(24) 
_refine_ls_extinction_expression 
 'Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^' 
_refine_ls_number_reflns          3827 
_refine_ls_number_parameters      292 
_refine_ls_number_restraints      6 
_refine_ls_R_factor_all           0.0808 
_refine_ls_R_factor_obs           0.0547 
_refine_ls_wR_factor_all          0.1356 
_refine_ls_wR_factor_obs          0.1235 
_refine_ls_goodness_of_fit_all    0.982 
_refine_ls_goodness_of_fit_obs    1.102 
_refine_ls_restrained_S_all       0.997 
_refine_ls_restrained_S_obs       1.122 
_refine_ls_shift/esd_max          -0.004 
_refine_ls_shift/esd_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_thermal_displace_type 
 _atom_site_occupancy 
 _atom_site_calc_flag 
 _atom_site_refinement_flags 
 _atom_site_disorder_group 
Fe1 Fe -0.16607(5) -0.11310(2) 0.09568(7) 0.0308(2) Uani 1 d . . 
O1 O -0.1534(2) 0.00286(11) 0.1017(3) 0.0368(7) Uani 1 d . . 
O2 O -0.1410(3) -0.02915(13) -0.1630(4) 0.0458(8) Uani 1 d . . 
O3 O 0.1052(3) -0.17272(11) 0.3067(3) 0.0379(7) Uani 1 d . . 
O4 O 0.1069(3) -0.21445(12) -0.0749(5) 0.0464(9) Uani 1 d . . 
H4O H 0.1137(57) -0.2373(23) -0.0973(80) 0.070 Uiso 1 d . . 
O5 O 0.5348(3) -0.1716(2) -0.6747(4) 0.0745(12) Uani 1 d . . 
O6 O 0.6684(4) -0.1758(2) -0.4714(5) 0.0871(14) Uani 1 d . . 
N1 N 0.5657(4) -0.1763(2) -0.5206(5) 0.0524(11) Uani 1 d . . 
C1 C -0.1364(5) 0.0318(2) 0.3979(6) 0.0509(13) Uani 1 d . . 
H1A H -0.1622(23) 0.0683(2) 0.3697(28) 0.076 Uiso 1 calc R . 
H1B H -0.0522(5) 0.0295(10) 0.3886(31) 0.076 Uiso 1 calc R . 
H1C H -0.1567(23) 0.0231(8) 0.5161(7) 0.076 Uiso 1 calc R . 
C2 C -0.1963(4) -0.0080(2) 0.2712(5) 0.0378(10) Uani 1 d . . 
H2 H -0.2813(4) -0.0002(2) 0.2672(5) 0.045 Uiso 1 calc R . 
C3 C -0.1798(4) -0.0656(2) 0.3259(5) 0.0374(10) Uani 1 d . . 
H3 H -0.2387(4) -0.0789(2) 0.4064(5) 0.045 Uiso 1 calc R . 
C4 C -0.0762(4) -0.0957(2) 0.3292(5) 0.0318(9) Uani 1 d . . 
H4 H -0.0687(4) -0.1252(2) 0.4161(5) 0.038 Uiso 1 calc R . 
C5 C 0.0071(3) -0.0941(2) 0.1993(4) 0.0287(9) Uani 1 d . . 
H5 H 0.0353(3) -0.0575(2) 0.1705(4) 0.034 Uiso 1 calc R . 
C6 C 0.0966(3) -0.1370(2) 0.1948(5) 0.0293(9) Uani 1 d . . 
C7 C 0.1818(3) -0.1339(2) 0.0475(5) 0.0288(8) Uani 1 d . . 
H7 H 0.1415(3) -0.1155(2) -0.0526(5) 0.035 Uiso 1 calc R . 
C7' C 0.2865(4) -0.0990(2) 0.1078(5) 0.0371(10) Uani 1 d . . 
H7'A H 0.3340(13) -0.0912(9) 0.0092(9) 0.056 Uiso 1 calc R . 
H7'B H 0.3332(13) -0.1184(5) 0.1959(26) 0.056 Uiso 1 calc R . 
H7'C H 0.2586(4) -0.0655(5) 0.1565(32) 0.056 Uiso 1 calc R . 
C8 C 0.2145(4) -0.1909(2) -0.0107(5) 0.0335(9) Uani 1 d . . 
H8 H 0.2452(4) -0.2118(2) 0.0914(5) 0.040 Uiso 1 calc R . 
C9 C 0.3063(4) -0.18919(15) -0.1474(5) 0.0304(9) Uani 1 d . . 
C10 C 0.2743(4) -0.1801(2) -0.3224(5) 0.0357(10) Uani 1 d . . 
H10 H 0.1948(4) -0.1766(2) -0.3571(5) 0.043 Uiso 1 calc R . 
C11 C 0.3588(4) -0.1760(2) -0.4446(5) 0.0391(10) Uani 1 d . . 
H11 H 0.3375(4) -0.1696(2) -0.5624(5) 0.047 Uiso 1 calc R . 
C12 C 0.4753(4) -0.1815(2) -0.3916(5) 0.0379(10) Uani 1 d . . 
C13 C 0.5104(4) -0.1915(2) -0.2194(5) 0.0410(11) Uani 1 d . . 
H13 H 0.5900(4) -0.1954(2) -0.1859(5) 0.049 Uiso 1 calc R . 
C14 C 0.4244(4) -0.1955(2) -0.0989(5) 0.0357(10) Uani 1 d . . 
H14 H 0.4461(4) -0.2026(2) 0.0184(5) 0.043 Uiso 1 calc R . 
C15 C -0.1530(3) -0.0395(2) -0.0123(5) 0.0349(10) Uani 1 d . . 
O16 O -0.4160(3) -0.0911(2) 0.0380(5) 0.0663(10) Uani 1 d . . 
C16 C -0.3201(4) -0.1025(2) 0.0588(6) 0.0448(11) Uani 1 d . . 
O17 O -0.0983(3) -0.15094(14) -0.2496(4) 0.0565(10) Uani 1 d . . 
C17 C -0.1239(4) -0.1374(2) -0.1158(5) 0.0385(10) Uani 1 d . . 
O18 O -0.1861(4) -0.22639(14) 0.2239(5) 0.0762(12) Uani 1 d . . 
C18 C -0.1766(4) -0.1834(2) 0.1789(6) 0.0442(11) Uani 1 d . . 
C19 C -0.5305(12) -0.0343(5) -0.5538(16) 0.089(4) Uiso 0.10 d PD -1 
H19A H -0.6131(12) -0.0441(5) -0.5449(16) 0.107 Uiso 0.10 calc PR -1 
H19B H -0.4969(12) -0.0630(5) -0.6243(16) 0.107 Uiso 0.10 calc PR -1 
Cl1 Cl -0.4805(5) -0.0451(2) -0.3782(8) 0.1215(13) Uiso 0.10 d PD -1 
Cl2 Cl -0.5351(29) 0.0150(11) -0.6792(32) 0.1215(13) Uiso 0.10 d PD -1 
C20 C -0.5305(12) -0.0343(5) -0.5538(16) 0.089(4) Uiso 0.40 d PD -2 
H20A H -0.6005(6) -0.0571(3) -0.5678(9) 0.107 Uiso 0.40 calc PR -2 
H20B H -0.4742(6) -0.0484(3) -0.6352(9) 0.107 Uiso 0.40 calc PR -2 
Cl3 Cl -0.4805(5) -0.0451(2) -0.3782(8) 0.1215(13) Uiso 0.40 d PD -2 
Cl4 Cl -0.5699(6) 0.0278(3) -0.6280(9) 0.1215(13) Uiso 0.40 d PD -2 
 
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 
Fe1 0.0321(4) 0.0280(3) 0.0327(3) 0.0008(3) 0.0046(2) -0.0045(3) 
O1 0.047(2) 0.0278(14) 0.0354(15) 0.0054(13) -0.0012(13) 0.0017(13) 
O2 0.057(2) 0.049(2) 0.032(2) 0.0120(14) 0.0056(14) -0.002(2) 
O3 0.048(2) 0.032(2) 0.034(2) 0.0124(13) 0.0027(13) 0.0064(13) 
O4 0.040(2) 0.036(2) 0.064(2) -0.014(2) 0.0067(15) -0.009(2) 
O5 0.072(3) 0.114(3) 0.038(2) 0.019(2) 0.015(2) -0.001(2) 
O6 0.047(3) 0.150(4) 0.065(3) 0.023(3) 0.018(2) 0.010(3) 
N1 0.048(3) 0.065(3) 0.045(2) 0.009(2) 0.015(2) 0.004(2) 
C1 0.073(4) 0.035(2) 0.044(3) -0.005(2) -0.005(2) 0.007(2) 
C2 0.039(2) 0.037(2) 0.037(2) -0.002(2) 0.003(2) 0.007(2) 
C3 0.043(3) 0.035(2) 0.035(2) -0.001(2) 0.012(2) 0.000(2) 
C4 0.042(2) 0.030(2) 0.024(2) 0.003(2) 0.003(2) 0.001(2) 
C5 0.036(2) 0.024(2) 0.026(2) 0.001(2) 0.001(2) -0.001(2) 
C6 0.030(2) 0.028(2) 0.029(2) 0.000(2) -0.004(2) -0.001(2) 
C7 0.029(2) 0.029(2) 0.028(2) 0.002(2) 0.000(2) 0.002(2) 
C7' 0.035(2) 0.032(2) 0.043(2) 0.003(2) -0.001(2) -0.002(2) 
C8 0.039(2) 0.030(2) 0.032(2) 0.002(2) 0.003(2) 0.001(2) 
C9 0.038(2) 0.023(2) 0.030(2) -0.002(2) 0.001(2) 0.002(2) 
C10 0.037(2) 0.033(2) 0.037(2) 0.002(2) -0.003(2) 0.004(2) 
C11 0.041(3) 0.045(3) 0.031(2) 0.006(2) -0.004(2) 0.000(2) 
C12 0.039(2) 0.042(2) 0.034(2) 0.002(2) 0.006(2) -0.001(2) 
C13 0.039(2) 0.043(3) 0.040(3) 0.000(2) 0.000(2) 0.001(2) 
C14 0.041(2) 0.038(2) 0.028(2) 0.001(2) -0.001(2) 0.003(2) 
C15 0.028(2) 0.034(2) 0.043(2) 0.003(2) 0.002(2) 0.000(2) 
O16 0.029(2) 0.077(3) 0.092(3) 0.005(2) -0.001(2) -0.005(2) 
C16 0.045(3) 0.039(3) 0.051(3) -0.003(2) 0.009(2) -0.014(2) 
O17 0.076(3) 0.061(2) 0.033(2) -0.004(2) 0.001(2) 0.007(2) 
C17 0.046(3) 0.033(2) 0.035(2) 0.002(2) -0.004(2) -0.002(2) 
O18 0.101(3) 0.035(2) 0.094(3) 0.008(2) 0.021(2) -0.013(2) 
C18 0.052(3) 0.038(3) 0.044(3) -0.002(2) 0.009(2) -0.004(2) 
 
_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 
Fe1 C16 1.790(5) . ? 
Fe1 C17 1.816(5) . ? 
Fe1 C18 1.859(5) . ? 
Fe1 C15 2.009(4) . ? 
Fe1 C4 2.073(4) . ? 
Fe1 C3 2.134(4) . ? 
Fe1 C5 2.154(4) . ? 
O1 C15 1.366(5) . ? 
O1 C2 1.436(5) . ? 
O2 C15 1.199(5) . ? 
O3 C6 1.233(4) . ? 
O4 C8 1.430(5) . ? 
O5 N1 1.225(5) . ? 
O6 N1 1.219(5) . ? 
N1 C12 1.468(6) . ? 
C1 C2 1.527(6) . ? 
C2 C3 1.495(6) . ? 
C3 C4 1.397(6) . ? 
C4 C5 1.409(5) . ? 
C5 C6 1.477(5) . ? 
C6 C7 1.526(5) . ? 
C7 C7' 1.531(5) . ? 
C7 C8 1.531(5) . ? 
C8 C9 1.516(6) . ? 
C9 C14 1.394(6) . ? 
C9 C10 1.396(5) . ? 
C10 C11 1.379(6) . ? 
C11 C12 1.382(6) . ? 
C12 C13 1.387(5) . ? 
C13 C14 1.382(6) . ? 
O16 C16 1.137(6) . ? 
O17 C17 1.131(5) . ? 
O18 C18 1.125(5) . ? 
C19 Cl1 1.466(11) . ? 
C19 Cl2 1.55(2) . ? 
C20 Cl3 1.466(11) . ? 
C20 Cl4 1.694(14) . ? 
 
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 
C16 Fe1 C17 101.8(2) . . ? 
C16 Fe1 C18 96.5(2) . . ? 
C17 Fe1 C18 91.2(2) . . ? 
C16 Fe1 C15 83.8(2) . . ? 
C17 Fe1 C15 84.5(2) . . ? 
C18 Fe1 C15 175.6(2) . . ? 
C16 Fe1 C4 123.6(2) . . ? 
C17 Fe1 C4 134.5(2) . . ? 
C18 Fe1 C4 86.2(2) . . ? 
C15 Fe1 C4 97.2(2) . . ? 
C16 Fe1 C3 86.8(2) . . ? 
C17 Fe1 C3 162.7(2) . . ? 
C18 Fe1 C3 102.9(2) . . ? 
C15 Fe1 C3 81.5(2) . . ? 
C4 Fe1 C3 38.8(2) . . ? 
C16 Fe1 C5 155.3(2) . . ? 
C17 Fe1 C5 97.3(2) . . ? 
C18 Fe1 C5 98.6(2) . . ? 
C15 Fe1 C5 82.6(2) . . ? 
C4 Fe1 C5 38.88(15) . . ? 
C3 Fe1 C5 70.9(2) . . ? 
C15 O1 C2 116.6(3) . . ? 
O6 N1 O5 122.2(4) . . ? 
O6 N1 C12 119.3(4) . . ? 
O5 N1 C12 118.6(4) . . ? 
O1 C2 C3 112.9(3) . . ? 
O1 C2 C1 107.2(4) . . ? 
C3 C2 C1 112.9(3) . . ? 
C4 C3 C2 127.6(4) . . ? 
C4 C3 Fe1 68.3(2) . . ? 
C2 C3 Fe1 107.8(3) . . ? 
C3 C4 C5 124.7(4) . . ? 
C3 C4 Fe1 73.0(2) . . ? 
C5 C4 Fe1 73.6(2) . . ? 
C4 C5 C6 119.1(3) . . ? 
C4 C5 Fe1 67.5(2) . . ? 
C6 C5 Fe1 117.5(3) . . ? 
O3 C6 C5 122.2(4) . . ? 
O3 C6 C7 121.3(4) . . ? 
C5 C6 C7 116.5(3) . . ? 
C6 C7 C7' 108.7(3) . . ? 
C6 C7 C8 109.9(3) . . ? 
C7' C7 C8 114.2(3) . . ? 
O4 C8 C9 112.6(3) . . ? 
O4 C8 C7 105.0(3) . . ? 
C9 C8 C7 111.2(3) . . ? 
C14 C9 C10 119.1(4) . . ? 
C14 C9 C8 120.2(3) . . ? 
C10 C9 C8 120.7(4) . . ? 
C11 C10 C9 120.3(4) . . ? 
C10 C11 C12 119.1(4) . . ? 
C11 C12 C13 122.3(4) . . ? 
C11 C12 N1 119.3(4) . . ? 
C13 C12 N1 118.4(4) . . ? 
C14 C13 C12 117.8(4) . . ? 
C13 C14 C9 121.4(4) . . ? 
O2 C15 O1 117.3(4) . . ? 
O2 C15 Fe1 127.3(3) . . ? 
O1 C15 Fe1 115.4(3) . . ? 
O16 C16 Fe1 173.9(4) . . ? 
O17 C17 Fe1 177.7(4) . . ? 
O18 C18 Fe1 177.2(4) . . ? 
Cl1 C19 Cl2 135.6(14) . . ? 
Cl3 C20 Cl4 124.2(10) . . ? 
 
_refine_diff_density_max    1.129 
_refine_diff_density_min   -0.646 
_refine_diff_density_rms    0.086