# Supplementary Material (ESI) for Perkin Transactions # This journal is © The Royal Society of Chemistry 2000 # CCDC Number: 188/254 data_RHPP _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_formula_moiety ? _chemical_formula_sum 'C84 H80 Cl8 F4 N4 O4' _chemical_formula_weight 1569.12 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source 'C' 'C' .0181 .0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 'H' 'H' .0000 .0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 'N' 'N' .0311 .0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 'O' 'O' .0492 .0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 'F' 'F' .0727 .0534 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 'Cl' 'Cl' .3639 .7018 '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 13.806(3) _cell_length_b 14.761(3) _cell_length_c 9.6180(19) _cell_angle_alpha 90.00 _cell_angle_beta 92.77(3) _cell_angle_gamma 90.00 _cell_volume 1957.8(7) _cell_formula_units_Z 1 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used 25 _cell_measurement_theta_min 40 _cell_measurement_theta_max 45 _exptl_crystal_description ? _exptl_crystal_colour ? _exptl_crystal_size_max ? _exptl_crystal_size_mid ? _exptl_crystal_size_min ? _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.331 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 816 _exptl_absorpt_coefficient_mu 3.137 _exptl_absorpt_correction_type none _exptl_absorpt_correction_T_min ? _exptl_absorpt_correction_T_max ? _exptl_special_details ; DUE TO DEGRADATION OF THE CRYSTAL BEFORE THE END OF THE DATA COLLECTION, NO ABSORPTION CORRECTION COULD BE APPLIED ; _diffrn_ambient_temperature 293(2) _diffrn_radiation_wavelength 1.54178 _diffrn_radiation_type CuK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'CAD-4' _diffrn_measurement_method 'q/2q' _diffrn_detector_area_resol_mean ? _diffrn_standards_number 3 _diffrn_standards_interval_count ? _diffrn_standards_interval_time 60 _diffrn_standards_decay_% 20 _diffrn_reflns_number 3018 _diffrn_reflns_av_R_equivalents 0.0661 _diffrn_reflns_av_sigmaI/netI 0.0699 _diffrn_reflns_limit_h_min -15 _diffrn_reflns_limit_h_max 15 _diffrn_reflns_limit_k_min 0 _diffrn_reflns_limit_k_max 16 _diffrn_reflns_limit_l_min 0 _diffrn_reflns_limit_l_max 10 _diffrn_reflns_theta_min 3.20 _diffrn_reflns_theta_max 58.92 _reflns_number_total 2820 _reflns_number_gt 1273 _reflns_threshold_expression >2sigma(I) _computing_data_collection ? _computing_cell_refinement ? _computing_data_reduction 'helena' _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 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 w=1/[\s^2^(Fo^2^)+(0.2182P)^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 mixed _refine_ls_extinction_method SHELXL _refine_ls_extinction_coef 0.0031(12) _refine_ls_extinction_expression 'Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^' _refine_ls_number_reflns 2820 _refine_ls_number_parameters 236 _refine_ls_number_restraints 0 _refine_ls_R_factor_gt 0.0957 _refine_ls_wR_factor_gt 0.2537 _refine_ls_goodness_of_fit_ref 0.971 _refine_ls_restrained_S_all 0.971 _refine_ls_shift/su_max 0.011 _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_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group Cl30 Cl 0.44175(16) 0.47550(14) 0.2501(2) 0.0971(9) Uani 1 d . . . Cl01 Cl 1.0122(2) 0.1910(3) 0.5619(3) 0.1644(16) Uani 1 d . . . C02 C 0.9179(7) 0.2060(10) 0.4383(9) 0.113(3) Uani 1 d . . . C03 C 0.8903(8) 0.2910(9) 0.4008(12) 0.127(4) Uani 1 d . . . H03 H 0.9217 0.3409 0.4413 0.152 Uiso 1 calc R . . C04 C 0.8156(7) 0.3032(7) 0.3026(11) 0.117(3) Uani 1 d . . . H04 H 0.7976 0.3614 0.2748 0.140 Uiso 1 calc R . . C05 C 0.7668(6) 0.2284(6) 0.2444(9) 0.089(2) Uani 1 d . . . C06 C 0.7969(7) 0.1445(7) 0.2833(10) 0.109(3) Uani 1 d . . . H06 H 0.7663 0.0940 0.2436 0.131 Uiso 1 calc R . . C07 C 0.8715(8) 0.1328(8) 0.3799(11) 0.125(3) Uani 1 d . . . H07 H 0.8907 0.0746 0.4061 0.150 Uiso 1 calc R . . C08 C 0.6871(6) 0.2412(6) 0.1355(8) 0.087(2) Uani 1 d . . . C09 C 0.6548(7) 0.3277(6) 0.0889(9) 0.099(3) Uani 1 d . . . H09 H 0.6830 0.3796 0.1277 0.118 Uiso 1 calc R . . C10 C 0.5829(7) 0.3354(6) -0.0119(9) 0.101(3) Uani 1 d . . . H10 H 0.5647 0.3928 -0.0433 0.121 Uiso 1 calc R . . N11 N 0.5376(5) 0.2630(4) -0.0674(7) 0.0871(18) Uani 1 d . . . C12 C 0.5654(6) 0.1795(5) -0.0237(9) 0.095(2) Uani 1 d . . . H12 H 0.5346 0.1291 -0.0637 0.113 Uiso 1 calc R . . C13 C 0.6360(6) 0.1669(6) 0.0756(9) 0.096(2) Uani 1 d . . . H13 H 0.6514 0.1084 0.1053 0.115 Uiso 1 calc R . . C14 C 0.4620(6) 0.2730(6) -0.1813(9) 0.095(2) Uani 1 d . . . H14A H 0.4759 0.2311 -0.2554 0.114 Uiso 1 calc R . . H14B H 0.4652 0.3339 -0.2188 0.114 Uiso 1 calc R . . C15 C 0.3618(6) 0.2560(6) -0.1370(9) 0.099(3) Uani 1 d . . . H15A H 0.3181 0.2567 -0.2191 0.119 Uiso 1 calc R . . H15B H 0.3595 0.1957 -0.0973 0.119 Uiso 1 calc R . . C16 C 0.3249(7) 0.3214(6) -0.0345(9) 0.104(3) Uani 1 d . . . H16A H 0.3674 0.3190 0.0488 0.125 Uiso 1 calc R . . H16B H 0.2613 0.3012 -0.0089 0.125 Uiso 1 calc R . . C17 C 0.3164(8) 0.4223(6) -0.0825(9) 0.109(3) Uani 1 d . . . H17 H 0.3817 0.4452 -0.0979 0.130 Uiso 1 calc R . . O18 O 0.2760(5) 0.4754(5) 0.0161(7) 0.130(2) Uani 1 d . . . H18 H 0.3082 0.4713 0.0897 0.196 Uiso 1 calc R . . C19 C 0.2553(7) 0.4309(6) -0.2180(9) 0.094(2) Uani 1 d . . . C20 C 0.1555(7) 0.4254(8) -0.2209(11) 0.123(3) Uani 1 d . . . H20 H 0.1237 0.4177 -0.1387 0.147 Uiso 1 calc R . . C21 C 0.1030(8) 0.4313(9) -0.3466(14) 0.138(4) Uani 1 d . . . H21 H 0.0357 0.4277 -0.3493 0.166 Uiso 1 calc R . . C22 C 0.1491(10) 0.4420(9) -0.4639(13) 0.130(4) Uani 1 d . . . C23 C 0.2476(9) 0.4488(6) -0.4667(11) 0.113(3) Uani 1 d . . . H23 H 0.2785 0.4559 -0.5498 0.135 Uiso 1 calc R . . C24 C 0.2988(6) 0.4445(6) -0.3410(11) 0.098(3) Uani 1 d . . . H24 H 0.3659 0.4511 -0.3394 0.118 Uiso 1 calc R . . F25 F 0.0977(5) 0.4459(6) -0.5904(7) 0.184(3) Uani 1 d . . . 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 Cl30 0.1065(16) 0.0903(13) 0.0945(14) 0.0026(11) 0.0051(11) 0.0021(11) Cl01 0.110(2) 0.259(4) 0.123(2) -0.019(2) -0.0034(17) 0.024(2) C02 0.079(6) 0.179(11) 0.083(6) -0.004(7) 0.014(5) 0.021(7) C03 0.097(7) 0.150(11) 0.133(9) -0.023(8) -0.008(6) 0.005(7) C04 0.113(8) 0.107(7) 0.130(8) -0.019(6) 0.006(6) 0.002(6) C05 0.086(6) 0.094(6) 0.087(5) -0.001(5) 0.020(4) 0.001(5) C06 0.104(7) 0.112(7) 0.112(7) 0.000(6) -0.006(6) 0.002(5) C07 0.117(8) 0.129(9) 0.130(8) 0.014(7) -0.005(7) -0.002(7) C08 0.087(5) 0.091(6) 0.083(5) -0.007(4) 0.025(4) -0.004(4) C09 0.116(7) 0.072(5) 0.108(6) -0.006(5) 0.011(6) -0.011(5) C10 0.110(7) 0.087(6) 0.105(6) 0.008(5) 0.001(5) -0.010(5) N11 0.094(5) 0.085(4) 0.083(4) -0.001(3) 0.016(4) -0.002(4) C12 0.101(6) 0.074(5) 0.110(6) -0.010(5) 0.018(5) 0.001(4) C13 0.105(6) 0.083(6) 0.099(6) 0.007(5) 0.005(5) 0.011(5) C14 0.092(6) 0.107(6) 0.088(5) 0.005(5) 0.021(5) 0.008(5) C15 0.108(7) 0.093(6) 0.097(6) -0.008(5) 0.004(5) 0.004(5) C16 0.121(7) 0.098(6) 0.093(6) -0.003(5) 0.019(5) -0.007(5) C17 0.139(8) 0.094(6) 0.093(6) -0.009(5) 0.017(6) 0.027(6) O18 0.142(6) 0.124(5) 0.126(5) -0.003(4) 0.020(4) 0.020(4) C19 0.098(7) 0.083(5) 0.102(6) 0.008(5) 0.013(5) -0.005(4) C20 0.096(7) 0.158(10) 0.115(7) 0.014(7) 0.011(6) -0.011(6) C21 0.097(7) 0.186(12) 0.132(9) 0.007(8) 0.008(8) -0.014(7) C22 0.122(9) 0.155(10) 0.113(8) 0.000(7) -0.018(8) -0.015(7) C23 0.127(9) 0.101(6) 0.111(7) 0.016(5) 0.021(7) 0.010(6) C24 0.088(6) 0.090(6) 0.118(7) 0.004(5) 0.017(6) 0.001(4) F25 0.169(6) 0.234(8) 0.143(5) 0.028(5) -0.046(5) -0.014(6) _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 Cl01 C02 1.733(9) . ? C02 C03 1.356(15) . ? C02 C07 1.364(14) . ? C03 C04 1.376(13) . ? C04 C05 1.396(12) . ? C05 C06 1.353(12) . ? C05 C08 1.494(11) . ? C06 C07 1.364(13) . ? C08 C13 1.412(11) . ? C08 C09 1.418(11) . ? C09 C10 1.358(12) . ? C10 N11 1.337(10) . ? N11 C12 1.353(10) . ? N11 C14 1.484(10) . ? C12 C13 1.345(11) . ? C14 C15 1.488(12) . ? C15 C16 1.486(12) . ? C16 C17 1.563(12) . ? C17 O18 1.370(10) . ? C17 C19 1.523(12) . ? C19 C24 1.366(12) . ? C19 C20 1.380(12) . ? C20 C21 1.382(14) . ? C21 C22 1.331(15) . ? C22 C23 1.365(14) . ? C22 F25 1.380(11) . ? C23 C24 1.373(12) . ? 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 C03 C02 C07 120.2(10) . . ? C03 C02 Cl01 119.5(10) . . ? C07 C02 Cl01 120.3(10) . . ? C02 C03 C04 119.7(11) . . ? C03 C04 C05 120.2(10) . . ? C06 C05 C04 118.5(9) . . ? C06 C05 C08 121.0(8) . . ? C04 C05 C08 120.4(8) . . ? C05 C06 C07 121.0(10) . . ? C06 C07 C02 120.3(11) . . ? C13 C08 C09 115.3(8) . . ? C13 C08 C05 121.6(8) . . ? C09 C08 C05 123.1(8) . . ? C10 C09 C08 120.7(8) . . ? N11 C10 C09 122.0(8) . . ? C10 N11 C12 119.0(7) . . ? C10 N11 C14 121.0(7) . . ? C12 N11 C14 119.9(7) . . ? C13 C12 N11 122.1(8) . . ? C12 C13 C08 120.9(8) . . ? N11 C14 C15 113.7(6) . . ? C16 C15 C14 115.7(8) . . ? C15 C16 C17 116.5(7) . . ? O18 C17 C19 108.5(8) . . ? O18 C17 C16 111.6(7) . . ? C19 C17 C16 111.3(8) . . ? C24 C19 C20 118.1(8) . . ? C24 C19 C17 120.3(9) . . ? C20 C19 C17 121.5(9) . . ? C19 C20 C21 119.7(10) . . ? C22 C21 C20 119.8(10) . . ? C21 C22 C23 122.9(10) . . ? C21 C22 F25 120.3(12) . . ? C23 C22 F25 116.7(12) . . ? C22 C23 C24 116.8(10) . . ? C19 C24 C23 122.7(9) . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag C07 C02 C03 C04 -0.6(16) . . . . ? Cl01 C02 C03 C04 179.9(8) . . . . ? C02 C03 C04 C05 1.7(15) . . . . ? C03 C04 C05 C06 -2.3(14) . . . . ? C03 C04 C05 C08 -178.6(9) . . . . ? C04 C05 C06 C07 1.8(14) . . . . ? C08 C05 C06 C07 178.1(9) . . . . ? C05 C06 C07 C02 -0.7(16) . . . . ? C03 C02 C07 C06 0.0(16) . . . . ? Cl01 C02 C07 C06 179.6(8) . . . . ? C06 C05 C08 C13 4.3(12) . . . . ? C04 C05 C08 C13 -179.5(8) . . . . ? C06 C05 C08 C09 -178.4(8) . . . . ? C04 C05 C08 C09 -2.1(12) . . . . ? C13 C08 C09 C10 -3.4(12) . . . . ? C05 C08 C09 C10 179.1(8) . . . . ? C08 C09 C10 N11 2.5(13) . . . . ? C09 C10 N11 C12 -1.3(12) . . . . ? C09 C10 N11 C14 -177.5(8) . . . . ? C10 N11 C12 C13 1.3(12) . . . . ? C14 N11 C12 C13 177.5(8) . . . . ? N11 C12 C13 C08 -2.4(13) . . . . ? C09 C08 C13 C12 3.4(12) . . . . ? C05 C08 C13 C12 -179.1(8) . . . . ? C10 N11 C14 C15 -107.6(9) . . . . ? C12 N11 C14 C15 76.2(9) . . . . ? N11 C14 C15 C16 64.9(10) . . . . ? C14 C15 C16 C17 61.9(11) . . . . ? C15 C16 C17 O18 176.0(8) . . . . ? C15 C16 C17 C19 54.6(12) . . . . ? O18 C17 C19 C24 133.7(9) . . . . ? C16 C17 C19 C24 -103.1(10) . . . . ? O18 C17 C19 C20 -46.3(12) . . . . ? C16 C17 C19 C20 76.9(11) . . . . ? C24 C19 C20 C21 1.6(15) . . . . ? C17 C19 C20 C21 -178.4(10) . . . . ? C19 C20 C21 C22 0.2(19) . . . . ? C20 C21 C22 C23 -1(2) . . . . ? C20 C21 C22 F25 178.5(11) . . . . ? C21 C22 C23 C24 -0.4(18) . . . . ? F25 C22 C23 C24 -179.7(10) . . . . ? C20 C19 C24 C23 -2.9(14) . . . . ? C17 C19 C24 C23 177.1(8) . . . . ? C22 C23 C24 C19 2.3(14) . . . . ? _diffrn_measured_fraction_theta_max .957 _diffrn_reflns_theta_full 58.92 _diffrn_measured_fraction_theta_full .957 _refine_diff_density_max .400 _refine_diff_density_min -.315 _refine_diff_density_rms .081