# Supplementary Material (ESI) for Perkin Transactions # This journal is © The Royal Society of Chemistry 2000 # CCDC Number: 207/384 data_compound18 _audit_creation_method SHELXL-97 _chemical_name_systematic ; 3-Hydroxy-2-hydroxymethyl-10-phenyl-2,3,9,10-tetrahydro-1- oxa-9-aza-anthrazen-4-one ; _chemical_name_common 'Ro 67-3926' _chemical_formula_moiety ? _chemical_formula_sum 'C19 H17 N O4' _chemical_formula_weight 323.34 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source 'C' 'C' 0.0181 0.0091 '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' 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 'O' 'O' 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Orthorhombic _symmetry_space_group_name_H-M P2(1)2(1)2(1) loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, -y, z+1/2' '-x, y+1/2, -z+1/2' 'x+1/2, -y+1/2, -z' _cell_length_a 7.0460(10) _cell_length_b 7.2040(10) _cell_length_c 31.591(4) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 1603.5(4) _cell_formula_units_Z 4 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used 19 _cell_measurement_theta_min 22.598 _cell_measurement_theta_max 56.022 _exptl_crystal_description 'rod' _exptl_crystal_colour 'colourless' _exptl_crystal_size_max 0.4 _exptl_crystal_size_mid 0.45 _exptl_crystal_size_min 0.4 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.339 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 680 _exptl_absorpt_coefficient_mu 0.775 _exptl_absorpt_correction_type ? _exptl_absorpt_correction_T_min ? _exptl_absorpt_correction_T_max ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 293(2) _diffrn_radiation_wavelength 1.54178 _diffrn_radiation_type CuK\a _diffrn_radiation_source 'rotating anode' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type P4 _diffrn_measurement_method Theta/2Theta _diffrn_standards_number 3 _diffrn_standards_interval_count 200 _diffrn_standards_interval_time ? _diffrn_standards_decay_% none _diffrn_reflns_number 2169 _diffrn_reflns_av_R_equivalents 0.0173 _diffrn_reflns_av_sigmaI/netI 0.0134 _diffrn_reflns_limit_h_min -1 _diffrn_reflns_limit_h_max 8 _diffrn_reflns_limit_k_min -1 _diffrn_reflns_limit_k_max 8 _diffrn_reflns_limit_l_min -1 _diffrn_reflns_limit_l_max 33 _diffrn_reflns_theta_min 2.80 _diffrn_reflns_theta_max 65.00 _reflns_number_total 1979 _reflns_number_gt 1934 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Siemens XSCANS' _computing_cell_refinement 'Siemens XSCANS' _computing_data_reduction 'Siemens XSCANS' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'XP, MOLOC' _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^)+(0.0844P)^2^+0.5433P] 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 0.0126(13) _refine_ls_extinction_expression 'Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^' _refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881' _refine_ls_abs_structure_Flack -0.9(5) _refine_ls_number_reflns 1979 _refine_ls_number_parameters 239 _refine_ls_number_restraints 5 _refine_ls_R_factor_all 0.0570 _refine_ls_R_factor_gt 0.0559 _refine_ls_wR_factor_ref 0.1529 _refine_ls_wR_factor_gt 0.1519 _refine_ls_goodness_of_fit_ref 1.137 _refine_ls_restrained_S_all 1.149 _refine_ls_shift/su_max 0.721 _refine_ls_shift/su_mean 0.032 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 N1 N 0.9540(3) 0.5858(4) 0.09376(9) 0.0541(7) Uani 1 d . . . H1A H 0.8404 0.6215 0.0880 0.065 Uiso 1 calc R . . O2 O 1.0512(3) 0.8257(3) 0.05517(7) 0.0562(6) Uani 1 d . . . O3 O 1.5999(3) 0.7434(5) 0.08690(12) 0.0969(11) Uani 1 d . . . O4 O 1.5213(4) 1.0197(5) 0.03669(12) 0.1072(12) Uani 1 d . . . H4A H 1.4820 1.1056 0.0221 0.161 Uiso 1 calc R . . C6A C 1.1024(14) 1.1144(11) 0.0214(3) 0.069(2) Uani 0.547(12) d PDU A 1 H6AA H 0.9755 1.1411 0.0316 0.083 Uiso 0.547(12) calc PR A 1 H6AB H 1.1755 1.2283 0.0231 0.083 Uiso 0.547(12) calc PR A 1 O5A O 1.0924(12) 1.0659(9) -0.01609(19) 0.102(3) Uani 0.547(12) d PU A 1 H5A H 0.9806 1.0571 -0.0231 1(3) Uiso 0.547(12) calc PR A 1 C6B C 1.155(3) 1.130(4) 0.0135(6) 0.34(3) Uani 0.453(12) d PD A 2 H6BA H 1.2026 1.2510 0.0220 0.406 Uiso 0.453(12) calc PR A 2 H6BB H 1.2107 1.0954 -0.0135 0.406 Uiso 0.453(12) calc PR A 2 O5B O 0.9518(15) 1.1240(19) 0.0126(4) 0.158(6) Uani 0.453(12) d P A 2 H5B H 0.9092 1.1946 0.0306 1.9(11) Uiso 0.453(12) calc PR A 2 C7 C 1.1908(5) 0.9733(5) 0.04965(12) 0.0618(9) Uani 1 d DU . . H7A H 1.2035 1.0330 0.0774 0.074 Uiso 1 calc R B 1 C8 C 1.3785(5) 0.8844(6) 0.04079(12) 0.0673(10) Uani 1 d . . . H8A H 1.3699 0.8130 0.0144 0.081 Uiso 1 calc R . . C9 C 1.4298(4) 0.7541(5) 0.07697(12) 0.0617(9) Uani 1 d . . . C10 C 1.2809(4) 0.6619(4) 0.09693(9) 0.0457(7) Uani 1 d . . . C11 C 1.3079(5) 0.5287(4) 0.13394(10) 0.0543(8) Uani 1 d . . . H11A H 1.4308 0.4671 0.1303 0.065 Uiso 1 calc R . . C12 C 1.3132(6) 0.6332(5) 0.17614(11) 0.0690(11) Uani 1 d . . . C13 C 1.4692(9) 0.7346(7) 0.18778(16) 0.1022(17) Uani 1 d . . . H13A H 1.5742 0.7383 0.1700 0.123 Uiso 1 calc R . . C14 C 1.4733(13) 0.8325(9) 0.2259(2) 0.137(3) Uani 1 d . . . H14A H 1.5802 0.9008 0.2334 0.164 Uiso 1 calc R . . C15 C 1.3226(18) 0.8275(9) 0.2517(2) 0.153(4) Uani 1 d . . . H15A H 1.3266 0.8911 0.2773 0.184 Uiso 1 calc R . . C16 C 1.1652(12) 0.7316(7) 0.24120(14) 0.114(2) Uani 1 d . . . H16A H 1.0612 0.7317 0.2593 0.137 Uiso 1 calc R . . C17 C 1.1570(8) 0.6334(5) 0.20374(12) 0.0822(13) Uani 1 d . . . H17A H 1.0480 0.5672 0.1968 0.099 Uiso 1 calc R . . C18 C 1.1563(5) 0.3808(4) 0.13333(10) 0.0527(8) Uani 1 d . . . C19 C 1.1808(7) 0.2112(5) 0.15370(12) 0.0734(11) Uani 1 d . . . H19A H 1.2967 0.1838 0.1663 0.088 Uiso 1 calc R . . C20 C 1.0353(9) 0.0832(5) 0.15538(14) 0.0870(14) Uani 1 d . . . H20A H 1.0543 -0.0295 0.1691 0.104 Uiso 1 calc R . . C21 C 0.8646(8) 0.1199(5) 0.13722(14) 0.0830(13) Uani 1 d . . . H21A H 0.7670 0.0332 0.1387 0.100 Uiso 1 calc R . . C22 C 0.8364(6) 0.2888(5) 0.11627(12) 0.0690(10) Uani 1 d . . . H22A H 0.7207 0.3148 0.1034 0.083 Uiso 1 calc R . . C23 C 0.9822(5) 0.4161(4) 0.11496(10) 0.0501(7) Uani 1 d . . . C24 C 1.1003(4) 0.6920(4) 0.08249(9) 0.0446(7) 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 N1 0.0362(11) 0.0509(14) 0.0752(16) 0.0175(13) 0.0009(12) 0.0004(12) O2 0.0450(11) 0.0619(13) 0.0618(12) 0.0245(10) -0.0093(9) -0.0045(11) O3 0.0369(11) 0.092(2) 0.162(3) 0.031(2) -0.0021(15) 0.0011(15) O4 0.0725(17) 0.099(2) 0.150(3) 0.054(2) 0.0217(19) -0.0244(19) C6A 0.068(5) 0.074(4) 0.066(3) 0.052(3) -0.010(4) -0.036(4) O5A 0.133(7) 0.096(4) 0.077(2) 0.023(3) -0.009(4) 0.023(5) C6B 0.091(11) 0.79(8) 0.133(14) 0.29(3) 0.007(9) 0.10(2) O5B 0.093(7) 0.174(11) 0.207(12) 0.098(10) -0.004(7) 0.024(8) C7 0.0492(16) 0.0580(19) 0.078(2) 0.0290(18) -0.0029(16) -0.0106(17) C8 0.0561(18) 0.076(2) 0.070(2) 0.0217(19) 0.0128(16) -0.012(2) C9 0.0388(14) 0.0611(19) 0.085(2) 0.0086(18) 0.0034(15) 0.0060(16) C10 0.0401(14) 0.0427(15) 0.0544(15) 0.0083(14) -0.0017(12) 0.0037(13) C11 0.0509(16) 0.0449(16) 0.0670(19) 0.0124(15) -0.0087(15) 0.0093(16) C12 0.098(3) 0.0419(16) 0.067(2) 0.0153(16) -0.036(2) 0.001(2) C13 0.126(4) 0.079(3) 0.102(3) 0.021(2) -0.056(3) -0.029(3) C14 0.197(8) 0.087(4) 0.126(5) 0.009(4) -0.081(5) -0.047(5) C15 0.289(12) 0.079(3) 0.091(4) 0.004(3) -0.060(6) -0.022(7) C16 0.214(7) 0.066(3) 0.063(2) -0.001(2) -0.012(3) 0.013(4) C17 0.128(4) 0.059(2) 0.060(2) 0.0067(17) -0.003(2) 0.009(3) C18 0.0669(19) 0.0366(14) 0.0546(16) 0.0042(13) 0.0004(15) 0.0047(16) C19 0.104(3) 0.0399(16) 0.076(2) 0.0098(16) -0.004(2) 0.015(2) C20 0.136(4) 0.0370(17) 0.088(3) 0.0135(17) 0.009(3) -0.002(3) C21 0.110(3) 0.0465(19) 0.093(3) 0.010(2) 0.021(3) -0.017(2) C22 0.070(2) 0.0543(19) 0.083(2) 0.0025(18) 0.0128(19) -0.012(2) C23 0.0560(17) 0.0369(14) 0.0573(17) 0.0054(13) 0.0075(14) -0.0004(15) C24 0.0409(13) 0.0446(14) 0.0482(14) 0.0114(12) -0.0006(12) 0.0004(13) _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 N1 C24 1.332(4) . ? N1 C23 1.408(4) . ? O2 C24 1.339(3) . ? O2 C7 1.460(4) . ? O3 C9 1.242(4) . ? O4 C8 1.407(4) . ? C6A O5A 1.237(12) . ? C6A C7 1.489(8) . ? C6B O5B 1.44(2) . ? C6B C7 1.626(15) . ? C7 C8 1.496(5) . ? C8 C9 1.522(5) . ? C9 C10 1.392(4) . ? C10 C24 1.369(4) . ? C10 C11 1.524(4) . ? C11 C18 1.509(5) . ? C11 C12 1.531(5) . ? C12 C13 1.370(6) . ? C12 C17 1.405(6) . ? C13 C14 1.396(8) . ? C14 C15 1.340(12) . ? C15 C16 1.348(11) . ? C16 C17 1.380(6) . ? C18 C23 1.381(5) . ? C18 C19 1.392(4) . ? C19 C20 1.380(6) . ? C20 C21 1.359(7) . ? C21 C22 1.399(5) . ? C22 C23 1.378(5) . ? 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 C24 N1 C23 121.1(2) . . ? C24 O2 C7 115.3(2) . . ? O5A C6A C7 113.9(8) . . ? O5B C6B C7 98.4(13) . . ? O2 C7 C6A 106.7(4) . . ? O2 C7 C8 107.8(3) . . ? C6A C7 C8 123.4(5) . . ? O2 C7 C6B 119.1(10) . . ? C6A C7 C6B 16.4(8) . . ? C8 C7 C6B 107.6(8) . . ? O4 C8 C7 110.7(3) . . ? O4 C8 C9 109.1(3) . . ? C7 C8 C9 109.5(3) . . ? O3 C9 C10 125.7(4) . . ? O3 C9 C8 117.2(3) . . ? C10 C9 C8 117.1(3) . . ? C24 C10 C9 118.3(3) . . ? C24 C10 C11 118.1(3) . . ? C9 C10 C11 123.6(3) . . ? C18 C11 C10 110.3(2) . . ? C18 C11 C12 112.1(3) . . ? C10 C11 C12 111.2(2) . . ? C13 C12 C17 117.5(4) . . ? C13 C12 C11 121.0(4) . . ? C17 C12 C11 121.4(4) . . ? C12 C13 C14 121.2(6) . . ? C15 C14 C13 119.7(7) . . ? C14 C15 C16 121.0(6) . . ? C15 C16 C17 120.6(7) . . ? C16 C17 C12 120.0(5) . . ? C23 C18 C19 117.8(3) . . ? C23 C18 C11 120.3(3) . . ? C19 C18 C11 121.8(3) . . ? C20 C19 C18 120.8(4) . . ? C21 C20 C19 120.8(3) . . ? C20 C21 C22 119.6(4) . . ? C23 C22 C21 119.1(4) . . ? C22 C23 C18 121.8(3) . . ? C22 C23 N1 119.1(3) . . ? C18 C23 N1 119.0(3) . . ? N1 C24 O2 112.6(2) . . ? N1 C24 C10 122.7(3) . . ? O2 C24 C10 124.7(3) . . ? _diffrn_measured_fraction_theta_max 0.962 _diffrn_reflns_theta_full 65.00 _diffrn_measured_fraction_theta_full 0.962 _refine_diff_density_max 0.450 _refine_diff_density_min -0.219 _refine_diff_density_rms 0.050 #===END data_x952 _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_formula_moiety ? _chemical_formula_sum 'C28 H27 Cl4 N O8' _chemical_formula_weight 647.31 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source 'C' 'C' 0.0181 0.0091 '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' 0.3639 0.7018 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 'N' 'N' 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 'O' 'O' 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Monoclinic _symmetry_space_group_name_H-M C2 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y, -z' 'x+1/2, y+1/2, z' '-x+1/2, y+1/2, -z' _cell_length_a 23.144(2) _cell_length_b 11.273(2) _cell_length_c 12.3570(10) _cell_angle_alpha 90.00 _cell_angle_beta 114.860(10) _cell_angle_gamma 90.00 _cell_volume 2925.2(6) _cell_formula_units_Z 4 _cell_measurement_temperature 193(2) _cell_measurement_reflns_used 20 _cell_measurement_theta_min 21.602 _cell_measurement_theta_max 56.084 _exptl_crystal_description plate _exptl_crystal_colour colourless _exptl_crystal_size_max 0.2 _exptl_crystal_size_mid 0.3 _exptl_crystal_size_min 0.3 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.470 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1336 _exptl_absorpt_coefficient_mu 4.116 _exptl_absorpt_correction_type ? _exptl_absorpt_correction_T_min ? _exptl_absorpt_correction_T_max ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 193(2) _diffrn_radiation_wavelength 1.54178 _diffrn_radiation_type CuK\a _diffrn_radiation_source 'rotating anode' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type P4 _diffrn_measurement_method Theta-2Theta _diffrn_standards_number 3 _diffrn_standards_interval_count 200 _diffrn_standards_decay_% none _diffrn_reflns_number 2784 _diffrn_reflns_av_R_equivalents 0.0231 _diffrn_reflns_av_sigmaI/netI 0.0161 _diffrn_reflns_limit_h_min -1 _diffrn_reflns_limit_h_max 23 _diffrn_reflns_limit_k_min -1 _diffrn_reflns_limit_k_max 13 _diffrn_reflns_limit_l_min -13 _diffrn_reflns_limit_l_max 13 _diffrn_reflns_theta_min 3.94 _diffrn_reflns_theta_max 64.94 _reflns_number_total 2549 _reflns_number_gt 2463 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Siemens XSCANS' _computing_cell_refinement 'Siemens XSCANS' _computing_data_reduction 'Siemens XSCANS' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'XP, MOLOC ' _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^)+(0.1110P)^2^+6.3521P] 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 0.0017(3) _refine_ls_extinction_expression 'Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^' _refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881' _refine_ls_abs_structure_Flack 0.02(4) _refine_ls_number_reflns 2549 _refine_ls_number_parameters 381 _refine_ls_number_restraints 1 _refine_ls_R_factor_all 0.0603 _refine_ls_R_factor_gt 0.0586 _refine_ls_wR_factor_ref 0.1627 _refine_ls_wR_factor_gt 0.1602 _refine_ls_goodness_of_fit_ref 1.048 _refine_ls_restrained_S_all 1.048 _refine_ls_shift/su_max 0.002 _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_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group N1 N -0.2306(2) -0.7048(4) -0.3175(3) 0.0290(10) Uani 1 d . . . O2 O -0.31890(15) -0.8200(3) -0.3988(3) 0.0281(8) Uani 1 d . . . O3 O -0.16260(16) -0.5488(3) -0.2604(3) 0.0269(8) Uani 1 d . . . O4 O -0.44703(18) -0.8542(4) -0.5537(3) 0.0454(11) Uani 1 d . . . H4A H -0.4571 -0.8560 -0.6257 0.068 Uiso 1 calc R . . O5 O -0.42834(16) -0.9403(4) -0.2810(3) 0.0336(9) Uani 1 d . . . H5A H -0.4092 -0.9828 -0.2230 0.050 Uiso 1 calc R . . O6 O -0.33475(16) -0.8344(4) -0.0828(3) 0.0318(9) Uani 1 d . . . O7 O -0.12893(16) -0.5903(3) 0.0895(3) 0.0291(8) Uani 1 d . . . O8 O -0.06947(15) -0.4043(3) 0.0279(3) 0.0269(8) Uani 1 d . . . H8A H -0.0960 -0.3777 0.0492 0.040 Uiso 1 calc R . . O9 O -0.04547(17) -0.4305(5) -0.2231(3) 0.0439(12) Uani 1 d . . . H9A H -0.0144 -0.4157 -0.1607 0.066 Uiso 1 calc R . . C10 C -0.2322(2) -0.6957(5) -0.4363(4) 0.0240(11) Uani 1 d . . . C11 C -0.2700(3) -0.6125(7) -0.5136(5) 0.0463(16) Uani 1 d . . . H11A H -0.2940 -0.5602 -0.4912 0.056 Uiso 1 calc R . . C12 C -0.2715(3) -0.6082(8) -0.6292(5) 0.0530(19) Uani 1 d . . . H12A H -0.2976 -0.5523 -0.6829 0.064 Uiso 1 calc R . . C13 C -0.2370(3) -0.6813(6) -0.6648(5) 0.0433(16) Uani 1 d . . . C14 C -0.2391(4) -0.6748(7) -0.7884(5) 0.058(2) Uani 1 d . . . H14A H -0.2689 -0.6148 -0.8336 0.087 Uiso 1 calc R . . H14B H -0.2522 -0.7501 -0.8273 0.087 Uiso 1 calc R . . H14C H -0.1976 -0.6553 -0.7828 0.087 Uiso 1 calc R . . C15 C -0.1978(4) -0.7621(7) -0.5818(6) 0.0569(19) Uani 1 d . . . H15A H -0.1723 -0.8121 -0.6030 0.068 Uiso 1 calc R . . C16 C -0.1955(4) -0.7705(7) -0.4689(6) 0.0543(18) Uani 1 d . . . H16A H -0.1694 -0.8264 -0.4153 0.065 Uiso 1 calc R . . C17 C -0.2747(2) -0.7730(5) -0.2976(4) 0.0252(11) Uani 1 d . . . C18 C -0.3580(2) -0.9117(5) -0.3782(4) 0.0260(11) Uani 1 d . . . H18A H -0.3309 -0.9796 -0.3389 0.031 Uiso 1 calc R . . C19 C -0.4068(3) -0.9502(6) -0.4988(4) 0.0348(13) Uani 1 d . . . H19A H -0.3856 -0.9765 -0.5477 0.042 Uiso 1 calc R . . H19B H -0.4315 -1.0159 -0.4898 0.042 Uiso 1 calc R . . C20 C -0.3854(2) -0.8611(5) -0.2960(4) 0.0263(11) Uani 1 d . . . H20A H -0.4087 -0.7885 -0.3325 0.032 Uiso 1 calc R . . C21 C -0.3301(2) -0.8273(5) -0.1791(4) 0.0258(11) Uani 1 d . . . C22 C -0.2738(2) -0.7858(5) -0.1883(4) 0.0255(11) Uani 1 d . . . C23 C -0.2157(2) -0.7521(5) -0.0776(4) 0.0252(11) Uani 1 d . . . H23A H -0.2296 -0.7229 -0.0177 0.030 Uiso 1 calc R . . C24 C -0.1821(2) -0.6525(5) -0.1099(4) 0.0266(12) Uani 1 d . . . C25 C -0.1364(2) -0.5812(4) -0.0159(4) 0.0240(11) Uani 1 d . . . C26 C -0.0963(2) -0.4973(5) -0.0524(4) 0.0243(11) Uani 1 d . . . H26A H -0.0614 -0.5435 -0.0565 0.029 Uiso 1 calc R . . C27 C -0.1369(2) -0.4502(5) -0.1772(4) 0.0264(11) Uani 1 d . . . H27A H -0.1724 -0.4044 -0.1750 0.032 Uiso 1 calc R . . C28 C -0.0997(3) -0.3721(5) -0.2235(4) 0.0349(13) Uani 1 d . . . H28A H -0.1270 -0.3476 -0.3043 0.042 Uiso 1 calc R . . H28B H -0.0863 -0.3013 -0.1745 0.042 Uiso 1 calc R . . C29 C -0.1902(2) -0.6343(5) -0.2233(4) 0.0250(11) Uani 1 d . . . C30 C -0.1743(2) -0.8612(5) -0.0282(4) 0.0322(13) Uani 1 d . . . C31 C -0.1823(4) -0.9312(6) 0.0570(5) 0.0529(17) Uani 1 d . . . H31A H -0.2115 -0.9081 0.0864 0.064 Uiso 1 calc R . . C32 C -0.1478(4) -1.0342(7) 0.0994(7) 0.064(2) Uani 1 d . . . H32A H -0.1547 -1.0810 0.1548 0.077 Uiso 1 calc R . . C33 C -0.1041(4) -1.0663(7) 0.0599(8) 0.074(3) Uani 1 d . . . H33A H -0.0796 -1.1339 0.0911 0.089 Uiso 1 calc R . . C34 C -0.0945(3) -0.9999(7) -0.0277(8) 0.063(2) Uani 1 d . . . H34A H -0.0652 -1.0243 -0.0564 0.076 Uiso 1 calc R . . C35 C -0.1298(3) -0.8974(6) -0.0701(6) 0.0508(17) Uani 1 d . . . H35A H -0.1237 -0.8521 -0.1273 0.061 Uiso 1 calc R . . Cl36 Cl -0.43328(19) -0.5371(6) -0.6886(4) 0.176(2) Uani 1 d . . . Cl37 Cl -0.40300(19) -0.5337(3) -0.4362(4) 0.1341(13) Uani 1 d . . . C38 C -0.4446(9) -0.5913(14) -0.5699(16) 0.148(7) Uani 1 d . . . H38A H -0.4736 -0.6521 -0.5802 0.177 Uiso 1 calc R . . Cl3A Cl 0.0472(3) -0.7776(9) -0.3176(10) 0.087(3) Uani 0.59(3) d P A 1 Cl3B Cl 0.009(2) -0.7585(11) -0.375(2) 0.158(12) Uani 0.41(3) d P A 2 Cl40 Cl -0.01538(12) -0.7510(2) -0.1605(2) 0.0849(7) Uani 1 d . . . C41 C -0.0099(4) -0.6984(9) -0.2852(9) 0.082(3) Uani 1 d . . . H41A H -0.0340 -0.6356 -0.3309 0.099 Uiso 1 calc R B 1 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 N1 0.033(2) 0.034(2) 0.019(2) -0.0047(19) 0.0109(17) -0.010(2) O2 0.0292(17) 0.0337(19) 0.0193(15) -0.0031(15) 0.0082(13) -0.0101(16) O3 0.0310(17) 0.0277(18) 0.0192(16) -0.0022(14) 0.0079(13) -0.0091(15) O4 0.041(2) 0.063(3) 0.0226(17) -0.0055(19) 0.0036(15) 0.001(2) O5 0.0288(18) 0.044(2) 0.0230(16) 0.0075(16) 0.0061(13) -0.0080(17) O6 0.0362(19) 0.038(2) 0.0248(17) -0.0011(16) 0.0162(14) -0.0079(17) O7 0.0373(19) 0.0314(19) 0.0170(17) -0.0008(15) 0.0100(14) -0.0053(16) O8 0.0254(16) 0.0293(18) 0.0257(16) -0.0088(15) 0.0104(13) -0.0066(15) O9 0.0272(19) 0.080(3) 0.0237(17) -0.002(2) 0.0102(14) -0.005(2) C10 0.028(2) 0.027(2) 0.019(2) -0.006(2) 0.0113(19) -0.005(2) C11 0.058(4) 0.059(4) 0.026(3) 0.011(3) 0.022(3) 0.017(3) C12 0.063(4) 0.072(5) 0.025(3) 0.016(3) 0.019(3) 0.014(4) C13 0.058(4) 0.050(4) 0.025(3) -0.009(3) 0.021(3) -0.022(3) C14 0.091(5) 0.061(5) 0.029(3) -0.011(3) 0.033(3) -0.026(4) C15 0.089(5) 0.051(4) 0.050(4) -0.002(3) 0.048(4) 0.014(4) C16 0.074(4) 0.052(4) 0.043(3) 0.012(3) 0.031(3) 0.018(4) C17 0.023(2) 0.029(3) 0.021(2) -0.004(2) 0.0071(19) -0.004(2) C18 0.029(2) 0.028(2) 0.018(2) -0.002(2) 0.0062(19) -0.007(2) C19 0.036(3) 0.041(3) 0.024(2) 0.000(2) 0.009(2) -0.011(3) C20 0.026(2) 0.030(3) 0.021(2) 0.003(2) 0.0086(19) -0.001(2) C21 0.031(3) 0.025(2) 0.020(2) 0.000(2) 0.0095(19) -0.002(2) C22 0.024(2) 0.032(3) 0.016(2) 0.001(2) 0.0044(19) -0.003(2) C23 0.028(2) 0.029(3) 0.018(2) -0.001(2) 0.0088(19) -0.006(2) C24 0.032(3) 0.029(3) 0.017(2) 0.002(2) 0.0090(19) -0.002(2) C25 0.026(2) 0.020(2) 0.025(2) 0.0004(19) 0.0095(19) 0.001(2) C26 0.025(2) 0.028(2) 0.019(2) -0.002(2) 0.0073(18) -0.001(2) C27 0.030(3) 0.026(2) 0.019(2) -0.004(2) 0.0052(19) -0.004(2) C28 0.041(3) 0.038(3) 0.024(2) -0.001(2) 0.012(2) -0.013(3) C29 0.025(2) 0.029(3) 0.019(2) -0.003(2) 0.0074(19) -0.004(2) C30 0.033(3) 0.024(2) 0.029(2) 0.003(2) 0.003(2) -0.004(2) C31 0.072(4) 0.040(4) 0.041(3) 0.011(3) 0.017(3) -0.007(4) C32 0.086(6) 0.035(4) 0.061(4) 0.021(4) 0.020(4) 0.000(4) C33 0.054(4) 0.040(4) 0.093(6) 0.023(4) -0.005(4) -0.003(4) C34 0.044(4) 0.044(4) 0.094(6) 0.004(4) 0.021(4) 0.011(3) C35 0.041(3) 0.040(3) 0.064(4) 0.007(3) 0.015(3) 0.002(3) Cl36 0.112(3) 0.184(5) 0.170(4) 0.028(4) -0.001(2) 0.017(3) Cl37 0.138(3) 0.097(2) 0.190(4) -0.040(3) 0.091(3) -0.021(2) C38 0.200(16) 0.094(10) 0.201(16) -0.053(11) 0.136(14) -0.073(11) Cl3A 0.089(4) 0.097(5) 0.078(5) -0.034(3) 0.038(3) 0.001(3) Cl3B 0.30(4) 0.109(7) 0.099(11) 0.007(7) 0.113(18) 0.028(11) Cl40 0.0988(16) 0.0746(15) 0.0936(16) 0.0035(13) 0.0526(13) -0.0025(13) C41 0.079(6) 0.054(5) 0.090(6) 0.008(5) 0.012(5) 0.006(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 N1 C17 1.381(7) . ? N1 C29 1.395(6) . ? N1 C10 1.456(6) . ? O2 C17 1.347(5) . ? O2 C18 1.465(6) . ? O3 C29 1.338(6) . ? O3 C27 1.460(6) . ? O4 C19 1.403(7) . ? O5 C20 1.405(6) . ? O6 C21 1.241(6) . ? O7 C25 1.243(6) . ? O8 C26 1.397(6) . ? O9 C28 1.417(7) . ? C10 C11 1.362(8) . ? C10 C16 1.371(9) . ? C11 C12 1.414(8) . ? C12 C13 1.344(10) . ? C13 C15 1.386(10) . ? C13 C14 1.509(8) . ? C15 C16 1.378(9) . ? C17 C22 1.350(7) . ? C18 C19 1.506(6) . ? C18 C20 1.516(7) . ? C20 C21 1.521(6) . ? C21 C22 1.433(7) . ? C22 C23 1.509(6) . ? C23 C24 1.511(7) . ? C23 C30 1.521(7) . ? C24 C29 1.350(7) . ? C24 C25 1.443(7) . ? C25 C26 1.520(7) . ? C26 C27 1.524(6) . ? C27 C28 1.503(8) . ? C30 C31 1.388(9) . ? C30 C35 1.396(9) . ? C31 C32 1.382(11) . ? C32 C33 1.344(13) . ? C33 C34 1.408(12) . ? C34 C35 1.383(10) . ? Cl36 C38 1.708(16) . ? Cl37 C38 1.655(16) . ? Cl3A C41 1.774(12) . ? Cl3B C41 1.515(17) . ? Cl40 C41 1.705(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 C17 N1 C29 117.1(4) . . ? C17 N1 C10 120.8(4) . . ? C29 N1 C10 121.6(4) . . ? C17 O2 C18 113.5(4) . . ? C29 O3 C27 114.7(4) . . ? C11 C10 C16 120.8(5) . . ? C11 C10 N1 119.5(5) . . ? C16 C10 N1 119.7(5) . . ? C10 C11 C12 117.9(6) . . ? C13 C12 C11 122.9(6) . . ? C12 C13 C15 117.0(5) . . ? C12 C13 C14 122.0(7) . . ? C15 C13 C14 120.9(7) . . ? C16 C15 C13 122.0(6) . . ? C10 C16 C15 119.3(6) . . ? O2 C17 C22 125.0(4) . . ? O2 C17 N1 112.5(4) . . ? C22 C17 N1 122.4(4) . . ? O2 C18 C19 107.0(4) . . ? O2 C18 C20 108.3(4) . . ? C19 C18 C20 114.9(4) . . ? O4 C19 C18 108.9(5) . . ? O5 C20 C18 111.6(4) . . ? O5 C20 C21 113.1(4) . . ? C18 C20 C21 108.1(4) . . ? O6 C21 C22 123.0(4) . . ? O6 C21 C20 121.2(4) . . ? C22 C21 C20 115.8(4) . . ? C17 C22 C21 118.8(4) . . ? C17 C22 C23 120.8(4) . . ? C21 C22 C23 120.3(4) . . ? C22 C23 C24 108.0(4) . . ? C22 C23 C30 109.3(4) . . ? C24 C23 C30 113.6(4) . . ? C29 C24 C25 119.0(5) . . ? C29 C24 C23 121.7(4) . . ? C25 C24 C23 119.1(4) . . ? O7 C25 C24 122.0(5) . . ? O7 C25 C26 121.9(4) . . ? C24 C25 C26 116.1(4) . . ? O8 C26 C25 113.6(4) . . ? O8 C26 C27 111.0(4) . . ? C25 C26 C27 108.9(4) . . ? O3 C27 C28 107.9(4) . . ? O3 C27 C26 110.0(4) . . ? C28 C27 C26 112.4(4) . . ? O9 C28 C27 112.0(5) . . ? O3 C29 C24 126.0(4) . . ? O3 C29 N1 112.0(4) . . ? C24 C29 N1 122.1(5) . . ? C31 C30 C35 118.0(6) . . ? C31 C30 C23 120.2(6) . . ? C35 C30 C23 121.7(5) . . ? C32 C31 C30 121.7(8) . . ? C33 C32 C31 119.5(7) . . ? C32 C33 C34 121.4(7) . . ? C35 C34 C33 118.5(8) . . ? C34 C35 C30 120.9(7) . . ? Cl37 C38 Cl36 118.8(8) . . ? Cl3B C41 Cl40 131.5(8) . . ? Cl3B C41 Cl3A 30.4(13) . . ? Cl40 C41 Cl3A 112.0(7) . . ? _diffrn_measured_fraction_theta_max 0.438 _diffrn_reflns_theta_full 64.94 _diffrn_measured_fraction_theta_full 0.438 _refine_diff_density_max 0.428 _refine_diff_density_min -0.602 _refine_diff_density_rms 0.080