# Supplementary Material (ESI) for ChemComm # This journal is © The Royal Society of Chemistry 2000 # CCDC Number: 182/1834 data_rab01 _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C36 H20 Cl8' _chemical_formula_weight 736.12 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' 'Cl' 'Cl' 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Orthorhombic _symmetry_space_group_name_H-M Cmc2(1) loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, z+1/2' 'x, -y, z+1/2' '-x, y, z' 'x+1/2, y+1/2, z' '-x+1/2, -y+1/2, z+1/2' 'x+1/2, -y+1/2, z+1/2' '-x+1/2, y+1/2, z' _cell_length_a 16.2594(8) _cell_length_b 20.0097(10) _cell_length_c 9.2417(5) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 3006.7(3) _cell_formula_units_Z 4 _cell_measurement_temperature 173(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description ? _exptl_crystal_colour ? _exptl_crystal_size_max 0.40 _exptl_crystal_size_mid 0.10 _exptl_crystal_size_min 0.10 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.626 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1488 _exptl_absorpt_coefficient_mu 0.778 _exptl_absorpt_correction_type none _exptl_absorpt_correction_T_min 0.7460 _exptl_absorpt_correction_T_max 0.9262 _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 173(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 ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 2035 _diffrn_reflns_av_R_equivalents 0.0000 _diffrn_reflns_av_sigmaI/netI 0.0307 _diffrn_reflns_limit_h_min 0 _diffrn_reflns_limit_h_max 17 _diffrn_reflns_limit_k_min 0 _diffrn_reflns_limit_k_max 21 _diffrn_reflns_limit_l_min -9 _diffrn_reflns_limit_l_max 9 _diffrn_reflns_theta_min 1.61 _diffrn_reflns_theta_max 22.50 _reflns_number_total 2035 _reflns_number_gt 1841 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'Bruker SMART' _computing_data_reduction 'Bruker SHELXTL' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Bruker SHELXTL' _computing_publication_material 'Bruker SHELXTL' _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^)+(0.1711P)^2^+5.2734P] 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 none _refine_ls_extinction_coef ? _refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881' _refine_ls_abs_structure_Flack 0.16(17) _refine_ls_number_reflns 2035 _refine_ls_number_parameters 216 _refine_ls_number_restraints 52 _refine_ls_R_factor_all 0.0810 _refine_ls_R_factor_gt 0.0761 _refine_ls_wR_factor_ref 0.2177 _refine_ls_wR_factor_gt 0.2122 _refine_ls_goodness_of_fit_ref 1.068 _refine_ls_restrained_S_all 1.056 _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 Cl1 Cl 0.0000 0.10615(16) 0.7226(5) 0.119(2) Uani 1 2 d SDU . . Cl2 Cl 0.0859(2) 0.22355(16) 0.7599(5) 0.1091(14) Uani 1 1 d DU . . Cl3 Cl 0.0000 0.19903(16) 0.4994(3) 0.0639(10) Uani 1 2 d SDU . . Cl4 Cl 0.0000 0.3835(2) 0.9203(4) 0.0950(14) Uani 1 2 d SDU . . Cl5 Cl 0.0000 0.3827(3) 0.6124(5) 0.172(4) Uani 1 2 d SDU . . Cl6 Cl 0.0865(2) 0.4788(3) 0.7636(8) 0.170(2) Uani 1 1 d DU . . C1 C 0.0474(4) 0.2724(3) 0.1954(7) 0.0286(15) Uani 1 1 d . . . C2 C 0.0968(4) 0.3193(3) 0.2626(8) 0.0331(16) Uani 1 1 d . . . H2 H 0.0775 0.3641 0.2642 0.040 Uiso 1 1 calc R . . C3 C 0.1709(4) 0.3069(3) 0.3268(9) 0.0316(16) Uani 1 1 d . . . C4 C 0.2194(4) 0.3601(3) 0.4078(9) 0.0341(16) Uani 1 1 d . . . H4A H 0.2742 0.3644 0.3649 0.051 Uiso 1 1 calc R . . H4B H 0.2246 0.3471 0.5097 0.051 Uiso 1 1 calc R . . H4C H 0.1905 0.4030 0.4012 0.051 Uiso 1 1 calc R . . C5 C 0.2026(4) 0.2413(3) 0.3292(8) 0.0281(15) Uani 1 1 d . . . C6 C 0.2598(4) 0.2133(3) 0.4285(9) 0.0328(16) Uani 1 1 d . . . H6 H 0.2989 0.2413 0.4746 0.039 Uiso 1 1 calc R . . C7 C 0.2591(4) 0.1482(3) 0.4578(8) 0.0292(16) Uani 1 1 d . . . H7 H 0.2971 0.1301 0.5253 0.035 Uiso 1 1 calc R . . C8 C 0.2027(3) 0.1069(3) 0.3897(7) 0.0248(15) Uani 1 1 d . . . C9 C 0.1738(4) 0.0465(3) 0.4452(8) 0.0280(15) Uani 1 1 d . . . C10 C 0.2237(4) 0.0134(3) 0.5676(8) 0.0289(16) Uani 1 1 d . . . H10A H 0.2205 0.0411 0.6550 0.043 Uiso 1 1 calc R . . H10B H 0.2813 0.0092 0.5377 0.043 Uiso 1 1 calc R . . H10C H 0.2012 -0.0310 0.5880 0.043 Uiso 1 1 calc R . . C11 C 0.0980(4) 0.0237(3) 0.4037(7) 0.0251(15) Uani 1 1 d . . . H11 H 0.0787 -0.0164 0.4473 0.030 Uiso 1 1 calc R . . C12 C 0.0453(4) 0.0553(3) 0.2996(7) 0.0228(14) Uani 1 1 d . . . C13 C 0.0850(4) 0.1047(3) 0.2240(7) 0.0260(15) Uani 1 1 d . . . C14 C 0.0406(4) 0.1544(3) 0.1528(7) 0.0201(13) Uani 1 1 d . . . C15 C 0.0842(4) 0.2134(3) 0.1727(7) 0.0220(14) Uani 1 1 d . . . C16 C 0.1585(4) 0.1982(3) 0.2430(8) 0.0255(14) Uani 1 1 d . . . C17 C 0.1593(4) 0.1313(3) 0.2754(7) 0.0233(14) Uani 1 1 d . . . C18 C 0.0000 0.18951(15) 0.6830(3) 0.039(3) Uani 1 2 d SD . . C19 C 0.0000 0.4304(2) 0.7658(3) 0.061(3) Uani 1 2 d SD . . 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 Cl1 0.263(7) 0.0286(16) 0.064(3) 0.0147(16) 0.000 0.000 Cl2 0.102(2) 0.096(2) 0.130(3) -0.015(2) -0.076(2) -0.0068(16) Cl3 0.105(3) 0.0563(18) 0.0305(16) 0.0017(13) 0.000 0.000 Cl4 0.113(3) 0.095(3) 0.076(3) 0.022(2) 0.000 0.000 Cl5 0.351(13) 0.089(4) 0.076(4) -0.008(3) 0.000 0.000 Cl6 0.121(3) 0.196(5) 0.194(5) 0.081(5) -0.021(3) -0.084(3) C1 0.034(3) 0.034(4) 0.017(3) 0.005(3) 0.005(3) -0.001(3) C2 0.043(4) 0.023(3) 0.033(4) 0.004(3) -0.002(3) -0.006(3) C3 0.033(4) 0.024(3) 0.038(4) 0.007(3) 0.011(3) -0.001(3) C4 0.036(4) 0.024(3) 0.042(4) -0.004(3) -0.006(3) -0.005(3) C5 0.021(3) 0.034(4) 0.030(3) 0.001(3) -0.003(3) -0.002(3) C6 0.032(3) 0.036(4) 0.031(4) -0.005(3) 0.006(3) -0.012(3) C7 0.026(3) 0.029(4) 0.033(4) -0.002(3) 0.000(3) 0.005(3) C8 0.017(3) 0.034(4) 0.023(3) 0.000(3) 0.011(3) 0.008(3) C9 0.028(3) 0.020(3) 0.036(4) -0.005(3) 0.008(3) 0.008(3) C10 0.029(3) 0.015(3) 0.043(4) 0.004(3) 0.009(3) -0.003(3) C11 0.028(3) 0.019(3) 0.029(4) -0.003(3) 0.002(3) 0.008(2) C12 0.031(3) 0.015(3) 0.022(4) -0.011(3) 0.007(3) 0.001(3) C13 0.035(4) 0.026(3) 0.017(3) -0.010(3) 0.007(3) 0.002(3) C14 0.026(3) 0.025(3) 0.009(3) -0.001(3) 0.002(2) -0.001(3) C15 0.025(3) 0.027(4) 0.014(3) 0.001(3) 0.000(3) -0.003(3) C16 0.028(3) 0.026(3) 0.022(3) 0.000(3) 0.011(3) -0.002(3) C17 0.026(3) 0.025(3) 0.019(3) -0.011(3) 0.008(3) -0.004(3) C18 0.050(6) 0.044(6) 0.024(6) -0.007(5) 0.000 0.000 C19 0.058(7) 0.043(6) 0.082(9) -0.004(7) 0.000 0.000 _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 Cl1 C18 1.7077(16) . ? Cl2 C18 1.7080(16) . ? Cl3 C18 1.7080(16) . ? Cl4 C19 1.7081(16) . ? Cl5 C19 1.7081(16) . ? Cl6 C19 1.7081(16) . ? C1 C15 1.340(9) . ? C1 C2 1.383(10) . ? C1 C1 1.542(14) 4 ? C2 C3 1.365(11) . ? C3 C5 1.410(10) . ? C3 C4 1.521(10) . ? C5 C16 1.375(9) . ? C5 C6 1.422(10) . ? C6 C7 1.330(9) . ? C7 C8 1.386(9) . ? C8 C17 1.361(9) . ? C8 C9 1.394(9) . ? C9 C11 1.370(9) . ? C9 C10 1.542(10) . ? C11 C12 1.435(9) . ? C12 C13 1.372(9) . ? C12 C12 1.472(13) 4 ? C13 C14 1.393(9) . ? C13 C17 1.403(9) . ? C14 C14 1.321(13) 4 ? C14 C15 1.390(9) . ? C15 C16 1.406(9) . ? C16 C17 1.373(8) . ? C18 Cl2 1.7080(16) 4 ? C19 Cl6 1.7081(16) 4 ? 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 C15 C1 C2 114.2(6) . . ? C15 C1 C1 116.5(4) . 4 ? C2 C1 C1 125.5(4) . 4 ? C3 C2 C1 125.7(6) . . ? C2 C3 C5 119.9(6) . . ? C2 C3 C4 122.9(6) . . ? C5 C3 C4 117.0(6) . . ? C16 C5 C3 112.6(6) . . ? C16 C5 C6 117.8(6) . . ? C3 C5 C6 128.1(6) . . ? C7 C6 C5 120.9(6) . . ? C6 C7 C8 119.8(6) . . ? C17 C8 C7 118.8(6) . . ? C17 C8 C9 114.9(6) . . ? C7 C8 C9 124.9(6) . . ? C11 C9 C8 119.3(6) . . ? C11 C9 C10 122.4(5) . . ? C8 C9 C10 117.7(5) . . ? C9 C11 C12 125.3(6) . . ? C13 C12 C11 112.2(5) . . ? C13 C12 C12 118.1(4) . 4 ? C11 C12 C12 126.7(3) . 4 ? C12 C13 C14 120.7(5) . . ? C12 C13 C17 120.4(6) . . ? C14 C13 C17 109.5(5) . . ? C14 C14 C15 120.6(4) 4 . ? C14 C14 C13 121.2(4) 4 . ? C15 C14 C13 106.3(5) . . ? C1 C15 C14 122.9(6) . . ? C1 C15 C16 120.0(6) . . ? C14 C15 C16 108.4(5) . . ? C17 C16 C5 118.8(6) . . ? C17 C16 C15 108.6(5) . . ? C5 C16 C15 125.5(6) . . ? C8 C17 C16 121.6(6) . . ? C8 C17 C13 125.0(6) . . ? C16 C17 C13 106.8(6) . . ? Cl1 C18 Cl3 108.8(2) . . ? Cl1 C18 Cl2 107.49(18) . 4 ? Cl3 C18 Cl2 111.64(19) . 4 ? Cl1 C18 Cl2 107.49(18) . . ? Cl3 C18 Cl2 111.6(2) . . ? Cl2 C18 Cl2 109.6(3) 4 . ? Cl6 C19 Cl6 110.8(5) 4 . ? Cl6 C19 Cl5 107.9(3) 4 . ? Cl6 C19 Cl5 107.9(3) . . ? Cl6 C19 Cl4 108.7(3) 4 . ? Cl6 C19 Cl4 108.7(3) . . ? Cl5 C19 Cl4 112.8(4) . . ? _diffrn_measured_fraction_theta_max 1.000 _diffrn_reflns_theta_full 22.50 _diffrn_measured_fraction_theta_full 1.000 _refine_diff_density_max 0.698 _refine_diff_density_min -0.735 _refine_diff_density_rms 0.111