# Supplementary Material (ESI) for Perkin Transactions # This journal is © The Royal Society of Chemistry 2000 # CCDC Number: 207/469 data_alk1 _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C16 H20 Cl N O7' _chemical_formula_weight 747.56 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' 'Cl' 'Cl' 0.3639 0.7018 '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 8.715(2) _cell_length_b 18.175(5) _cell_length_c 21.948(5) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 3476.4(15) _cell_formula_units_Z 8 _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 0.80 _exptl_crystal_size_mid 0.53 _exptl_crystal_size_min 0.45 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.428 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1568 _exptl_absorpt_coefficient_mu 2.300 _exptl_absorpt_correction_type ? _exptl_absorpt_correction_T_min 0.2606 _exptl_absorpt_correction_T_max 0.4243 _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _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 ? _diffrn_measurement_method ? _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 5026 _diffrn_reflns_av_R_equivalents 0.0576 _diffrn_reflns_av_sigmaI/netI 0.0713 _diffrn_reflns_limit_h_min -9 _diffrn_reflns_limit_h_max 9 _diffrn_reflns_limit_k_min -19 _diffrn_reflns_limit_k_max 19 _diffrn_reflns_limit_l_min -23 _diffrn_reflns_limit_l_max 23 _diffrn_reflns_theta_min 3.16 _diffrn_reflns_theta_max 55.00 _reflns_number_total 4384 _reflns_number_gt 3386 _reflns_threshold_expression >2sigma(I) _computing_data_collection ? _computing_cell_refinement ? _computing_data_reduction ? _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 _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.1442P)^2^+5.6864P] 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 0.0010(2) _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 -0.01(4) _refine_ls_number_reflns 4384 _refine_ls_number_parameters 462 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.1119 _refine_ls_R_factor_gt 0.0885 _refine_ls_wR_factor_ref 0.2506 _refine_ls_wR_factor_gt 0.2253 _refine_ls_goodness_of_fit_ref 1.012 _refine_ls_restrained_S_all 1.012 _refine_ls_shift/su_max 0.065 _refine_ls_shift/su_mean 0.007 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_multiplicit _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group O1A O 1.4529(8) 0.1232(3) -0.2534(2) 0.0615(17) Uani 1 1 d . . . C2A C 1.5510(10) 0.0918(5) -0.3029(3) 0.050(2) Uani 1 1 d . . . H2A H 1.6581 0.1061 -0.2962 0.060 Uiso 1 1 calc R . . C3A C 1.5371(11) 0.0089(4) -0.2990(3) 0.053(2) Uani 1 1 d . . . H3A1 H 1.6374 -0.0141 -0.2967 0.064 Uiso 1 1 calc R . . H3A2 H 1.4824 -0.0106 -0.3339 0.064 Uiso 1 1 calc R . . C3AA C 1.4470(10) -0.0034(4) -0.2407(4) 0.046(2) Uani 1 1 d . . . C4A C 1.3974(9) -0.0631(4) -0.2092(4) 0.046(2) Uani 1 1 d . . . C4AA C 1.3029(10) -0.0498(5) -0.1549(4) 0.049(2) Uani 1 1 d . . . C5A C 1.2461(12) -0.1097(6) -0.1210(5) 0.068(3) Uani 1 1 d . . . H5A H 1.2673 -0.1576 -0.1333 0.082 Uiso 1 1 calc R . . C6A C 1.1612(13) -0.0976(6) -0.0706(5) 0.080(3) Uani 1 1 d . . . H6A H 1.1257 -0.1374 -0.0480 0.096 Uiso 1 1 calc R . . C7A C 1.1260(12) -0.0265(6) -0.0521(5) 0.076(3) Uani 1 1 d . . . H7A H 1.0659 -0.0193 -0.0176 0.091 Uiso 1 1 calc R . . C8A C 1.1779(11) 0.0323(6) -0.0836(4) 0.061(2) Uani 1 1 d . . . H8A H 1.1550 0.0797 -0.0706 0.073 Uiso 1 1 calc R . . C8AA C 1.2674(9) 0.0208(4) -0.1365(4) 0.043(2) Uani 1 1 d . . . N9A N 1.3189(8) 0.0811(3) -0.1706(3) 0.0484(18) Uani 1 1 d . . . C9A C 1.2764(13) 0.1572(5) -0.1538(4) 0.072(3) Uani 1 1 d . . . H9A1 H 1.3251 0.1911 -0.1812 0.109 Uiso 1 1 calc R . . H9A2 H 1.3095 0.1671 -0.1129 0.109 Uiso 1 1 calc R . . H9A3 H 1.1671 0.1629 -0.1563 0.109 Uiso 1 1 calc R . . C9AA C 1.4046(9) 0.0661(5) -0.2207(3) 0.046(2) Uani 1 1 d . . . O4A O 1.4233(8) -0.1334(3) -0.2201(3) 0.0679(19) Uani 1 1 d . . . C4'A C 1.5125(16) -0.1577(5) -0.2704(4) 0.088(4) Uani 1 1 d . . . H4'1 H 1.4613 -0.1452 -0.3077 0.131 Uiso 1 1 calc R . . H4'2 H 1.5254 -0.2101 -0.2681 0.131 Uiso 1 1 calc R . . H4'3 H 1.6113 -0.1344 -0.2693 0.131 Uiso 1 1 calc R . . C1'A C 1.4927(11) 0.1265(5) -0.3636(4) 0.060(2) Uani 1 1 d . . . C2'A C 1.4870(16) 0.2078(5) -0.3599(4) 0.082(3) Uani 1 1 d . . . H2'1 H 1.4789 0.2280 -0.4001 0.123 Uiso 1 1 calc R . . H2'2 H 1.5788 0.2256 -0.3408 0.123 Uiso 1 1 calc R . . H2'3 H 1.3994 0.2224 -0.3362 0.123 Uiso 1 1 calc R . . C3'A C 1.6039(13) 0.1006(6) -0.4139(4) 0.075(3) Uani 1 1 d . . . H3'1 H 1.6044 0.0478 -0.4155 0.113 Uiso 1 1 calc R . . H3'2 H 1.7055 0.1180 -0.4050 0.113 Uiso 1 1 calc R . . H3'3 H 1.5712 0.1199 -0.4525 0.113 Uiso 1 1 calc R . . O1'A O 1.3475(8) 0.0966(4) -0.3788(3) 0.0718(19) Uani 1 1 d . . . H1'A H 1.2877 0.1033 -0.3505 0.108 Uiso 1 1 calc R . . Cl1A Cl 0.9707(2) 0.15108(12) 0.04583(9) 0.0563(6) Uani 1 1 d . . . O5A O 1.0804(12) 0.1263(12) 0.0841(4) 0.237(9) Uani 1 1 d . . . O6A O 0.8745(13) 0.1995(6) 0.0755(6) 0.170(5) Uani 1 1 d . . . O7A O 1.0408(15) 0.1813(5) -0.0050(4) 0.142(4) Uani 1 1 d . . . O8A O 0.8831(12) 0.0881(5) 0.0293(6) 0.144(4) Uani 1 1 d . . . O1B O 0.5162(7) 0.1094(3) 0.0136(2) 0.0540(15) Uani 1 1 d . . . C2B C 0.4306(10) 0.0715(5) 0.0633(3) 0.050(2) Uani 1 1 d . . . H2B H 0.3204 0.0803 0.0582 0.060 Uiso 1 1 calc R . . C3B C 0.4641(12) -0.0104(5) 0.0548(3) 0.060(2) Uani 1 1 d . . . H3B1 H 0.3697 -0.0385 0.0525 0.072 Uiso 1 1 calc R . . H3B2 H 0.5257 -0.0292 0.0882 0.072 Uiso 1 1 calc R . . C3AB C 0.5528(10) -0.0142(4) -0.0056(3) 0.046(2) Uani 1 1 d . . . C4B C 0.6112(9) -0.0688(5) -0.0410(4) 0.048(2) Uani 1 1 d . . . C4AB C 0.6969(10) -0.0473(5) -0.0938(4) 0.052(2) Uani 1 1 d . . . C5B C 0.7653(12) -0.0995(6) -0.1322(5) 0.070(3) Uani 1 1 d . . . H5B H 0.7581 -0.1492 -0.1224 0.084 Uiso 1 1 calc R . . C6B C 0.8429(13) -0.0790(8) -0.1842(5) 0.086(4) Uani 1 1 d . . . H6B H 0.8808 -0.1150 -0.2103 0.103 Uiso 1 1 calc R . . C7B C 0.8650(13) -0.0056(7) -0.1980(5) 0.085(3) Uani 1 1 d . . . H7B H 0.9215 0.0080 -0.2322 0.101 Uiso 1 1 calc R . . C8B C 0.8030(10) 0.0464(6) -0.1609(4) 0.065(3) Uani 1 1 d . . . H8B H 0.8184 0.0958 -0.1698 0.078 Uiso 1 1 calc R . . C8AB C 0.7157(9) 0.0268(5) -0.1091(4) 0.049(2) Uani 1 1 d . . . N9B N 0.6514(8) 0.0819(4) -0.0732(3) 0.0462(17) Uani 1 1 d . . . C9B C 0.6731(13) 0.1589(5) -0.0852(4) 0.069(3) Uani 1 1 d . . . H9B1 H 0.6121 0.1873 -0.0573 0.103 Uiso 1 1 calc R . . H9B2 H 0.6422 0.1697 -0.1262 0.103 Uiso 1 1 calc R . . H9B3 H 0.7794 0.1713 -0.0801 0.103 Uiso 1 1 calc R . . C9AB C 0.5768(9) 0.0591(4) -0.0227(4) 0.046(2) Uani 1 1 d . . . O4B O 0.6017(8) -0.1405(3) -0.0335(3) 0.0709(19) Uani 1 1 d . . . C4'B C 0.5018(17) -0.1709(5) 0.0147(4) 0.083(3) Uani 1 1 d . . . H4'4 H 0.5180 -0.1442 0.0519 0.125 Uiso 1 1 calc R . . H4'5 H 0.5261 -0.2219 0.0209 0.125 Uiso 1 1 calc R . . H4'6 H 0.3964 -0.1664 0.0025 0.125 Uiso 1 1 calc R . . C1'B C 0.4838(9) 0.1049(5) 0.1236(3) 0.049(2) Uani 1 1 d . . . C2'B C 0.4756(15) 0.1859(5) 0.1213(4) 0.079(3) Uani 1 1 d . . . H2'4 H 0.4387 0.2043 0.1596 0.118 Uiso 1 1 calc R . . H2'5 H 0.4068 0.2006 0.0894 0.118 Uiso 1 1 calc R . . H2'6 H 0.5759 0.2055 0.1134 0.118 Uiso 1 1 calc R . . C3'B C 0.3863(10) 0.0712(6) 0.1739(4) 0.063(3) Uani 1 1 d . . . H3'4 H 0.3949 0.0185 0.1725 0.094 Uiso 1 1 calc R . . H3'5 H 0.2811 0.0851 0.1683 0.094 Uiso 1 1 calc R . . H3'6 H 0.4216 0.0886 0.2128 0.094 Uiso 1 1 calc R . . O1'B O 0.6391(7) 0.0815(5) 0.1368(3) 0.077(2) Uani 1 1 d . . . H1'B H 0.6974 0.0975 0.1106 0.115 Uiso 1 1 calc R . . Cl1B Cl 0.5017(3) 0.80815(15) 0.20263(12) 0.0743(8) Uani 1 1 d . . . O5B O 0.583(3) 0.7806(11) 0.1552(6) 0.270(10) Uani 1 1 d . . . O6B O 0.467(3) 0.8727(5) 0.1941(10) 0.318(14) Uani 1 1 d . . . O7B O 0.6059(17) 0.8100(8) 0.2521(5) 0.188(6) Uani 1 1 d . . . O8B O 0.3948(16) 0.7554(8) 0.2220(7) 0.189(6) Uani 1 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 O1A 0.088(5) 0.053(4) 0.044(3) 0.000(3) 0.005(3) -0.005(3) C2A 0.046(5) 0.067(6) 0.038(4) -0.005(4) 0.001(4) -0.001(4) C3A 0.061(5) 0.062(5) 0.038(4) 0.000(4) 0.004(4) 0.009(4) C3AA 0.056(5) 0.036(4) 0.045(5) -0.001(4) -0.004(4) 0.007(4) C4A 0.049(5) 0.045(5) 0.044(5) -0.002(4) -0.007(4) 0.007(4) C4AA 0.048(5) 0.056(5) 0.044(5) 0.009(4) -0.009(4) 0.005(4) C5A 0.081(7) 0.057(6) 0.067(6) 0.005(5) 0.012(6) 0.010(5) C6A 0.089(8) 0.071(7) 0.080(7) 0.026(6) 0.028(7) 0.002(6) C7A 0.077(7) 0.092(8) 0.058(6) 0.017(6) 0.022(6) -0.003(6) C8A 0.061(6) 0.076(7) 0.046(5) -0.006(5) 0.009(5) 0.010(5) C8AA 0.048(5) 0.038(5) 0.044(5) -0.004(4) 0.000(4) 0.010(4) N9A 0.057(4) 0.042(4) 0.045(4) -0.004(3) -0.010(4) 0.006(3) C9A 0.104(8) 0.046(5) 0.067(6) -0.006(5) 0.022(6) 0.000(6) C9AA 0.051(5) 0.052(5) 0.034(4) -0.006(4) 0.001(4) -0.009(4) O4A 0.095(5) 0.049(4) 0.059(4) 0.004(3) 0.007(4) 0.016(3) C4'A 0.137(10) 0.069(6) 0.057(6) -0.016(5) 0.006(7) 0.047(7) C1'A 0.073(6) 0.064(6) 0.044(5) 0.002(4) -0.012(5) -0.013(5) C2'A 0.129(10) 0.056(6) 0.061(6) 0.002(5) -0.001(7) -0.018(7) C3'A 0.086(7) 0.103(8) 0.037(5) 0.008(5) 0.006(5) -0.010(6) O1'A 0.071(4) 0.070(5) 0.075(4) -0.003(4) -0.028(4) -0.008(4) Cl1A 0.0466(11) 0.0714(14) 0.0510(12) -0.0006(10) -0.0020(10) -0.0015(11) O5A 0.090(7) 0.54(3) 0.078(6) 0.066(11) -0.012(6) 0.107(12) O6A 0.140(9) 0.146(9) 0.224(13) -0.072(9) 0.045(9) 0.052(8) O7A 0.186(11) 0.138(8) 0.103(7) 0.042(6) 0.053(8) -0.021(8) O8A 0.120(8) 0.093(6) 0.219(12) -0.015(7) 0.005(8) -0.033(6) O1B 0.071(4) 0.051(3) 0.041(3) -0.001(3) 0.010(3) 0.004(3) C2B 0.047(5) 0.069(6) 0.034(4) 0.006(4) 0.003(4) -0.002(4) C3B 0.085(7) 0.058(5) 0.038(5) -0.001(4) 0.009(5) -0.012(5) C3AB 0.061(5) 0.044(5) 0.034(4) 0.003(3) -0.009(4) -0.009(4) C4B 0.052(5) 0.048(5) 0.045(5) -0.005(4) -0.006(4) -0.003(4) C4AB 0.055(5) 0.057(6) 0.045(5) -0.012(4) -0.004(4) 0.006(4) C5B 0.075(7) 0.070(7) 0.065(7) -0.010(5) 0.012(6) 0.010(6) C6B 0.076(8) 0.113(10) 0.069(7) -0.027(7) 0.017(6) 0.015(7) C7B 0.078(8) 0.104(9) 0.072(7) -0.006(7) 0.029(6) 0.005(7) C8B 0.047(5) 0.099(8) 0.047(5) 0.007(5) 0.002(5) -0.009(5) C8AB 0.040(5) 0.067(6) 0.040(5) -0.011(4) -0.008(4) 0.001(4) N9B 0.050(4) 0.050(4) 0.038(4) 0.006(3) 0.000(3) -0.007(3) C9B 0.095(7) 0.052(6) 0.059(6) 0.011(5) 0.003(6) -0.001(5) C9AB 0.046(5) 0.052(5) 0.040(5) -0.007(4) -0.007(4) 0.005(4) O4B 0.105(5) 0.045(4) 0.062(4) -0.005(3) 0.015(4) -0.003(3) C4'B 0.129(10) 0.056(6) 0.065(6) 0.004(5) 0.002(7) -0.019(7) C1'B 0.040(5) 0.066(6) 0.039(4) 0.002(4) -0.009(4) 0.007(4) C2'B 0.107(9) 0.058(6) 0.071(6) -0.010(5) 0.011(7) -0.004(6) C3'B 0.053(5) 0.099(8) 0.036(5) 0.002(5) -0.008(4) 0.006(5) O1'B 0.049(4) 0.118(6) 0.064(4) 0.011(4) -0.015(3) 0.006(4) Cl1B 0.0753(18) 0.0807(18) 0.0669(15) 0.0099(12) 0.0060(14) -0.0039(15) O5B 0.35(2) 0.33(2) 0.131(10) -0.018(13) 0.104(13) 0.110(19) O6B 0.51(3) 0.048(6) 0.39(3) 0.011(10) -0.17(3) 0.040(12) O7B 0.215(13) 0.234(14) 0.116(8) 0.043(9) -0.073(9) -0.068(12) O8B 0.176(12) 0.194(12) 0.198(13) -0.012(10) 0.011(10) -0.086(10) _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 O1A C9AA 1.330(10) . ? O1A C2A 1.496(10) . ? C2A C3A 1.514(11) . ? C2A C1'A 1.559(11) . ? C3A C3AA 1.518(11) . ? C3AA C4A 1.357(11) . ? C3AA C9AA 1.388(11) . ? C4A O4A 1.319(10) . ? C4A C4AA 1.467(11) . ? C4AA C8AA 1.381(11) . ? C4AA C5A 1.408(13) . ? C5A C6A 1.348(14) . ? C6A C7A 1.389(14) . ? C7A C8A 1.349(13) . ? C8A C8AA 1.415(11) . ? C8AA N9A 1.401(10) . ? N9A C9AA 1.356(10) . ? N9A C9A 1.480(10) . ? O4A C4'A 1.420(11) . ? C1'A O1'A 1.417(11) . ? C1'A C2'A 1.481(13) . ? C1'A C3'A 1.541(13) . ? Cl1A O5A 1.349(9) . ? Cl1A O6A 1.379(9) . ? Cl1A O7A 1.386(8) . ? Cl1A O8A 1.423(9) . ? O1B C9AB 1.321(9) . ? O1B C2B 1.490(9) . ? C2B C1'B 1.528(11) . ? C2B C3B 1.529(12) . ? C3B C3AB 1.536(11) . ? C3AB C4B 1.360(11) . ? C3AB C9AB 1.401(11) . ? C4B O4B 1.316(10) . ? C4B C4AB 1.433(12) . ? C4AB C8AB 1.397(12) . ? C4AB C5B 1.402(12) . ? C5B C6B 1.377(15) . ? C6B C7B 1.381(15) . ? C7B C8B 1.359(14) . ? C8B C8AB 1.415(12) . ? C8AB N9B 1.392(10) . ? N9B C9AB 1.350(10) . ? N9B C9B 1.437(10) . ? O4B C4'B 1.477(12) . ? C1'B O1'B 1.448(10) . ? C1'B C2'B 1.475(12) . ? C1'B C3'B 1.523(11) . ? Cl1B O6B 1.226(11) . ? Cl1B O5B 1.355(13) . ? Cl1B O8B 1.403(12) . ? Cl1B O7B 1.416(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 C9AA O1A C2A 106.0(6) . . ? O1A C2A C3A 107.0(6) . . ? O1A C2A C1'A 106.3(7) . . ? C3A C2A C1'A 115.1(7) . . ? C2A C3A C3AA 103.7(6) . . ? C4A C3AA C9AA 118.8(8) . . ? C4A C3AA C3A 135.4(7) . . ? C9AA C3AA C3A 105.7(7) . . ? O4A C4A C3AA 128.8(8) . . ? O4A C4A C4AA 113.8(7) . . ? C3AA C4A C4AA 117.4(7) . . ? C8AA C4AA C5A 118.9(8) . . ? C8AA C4AA C4A 121.1(7) . . ? C5A C4AA C4A 120.0(8) . . ? C6A C5A C4AA 120.1(10) . . ? C5A C6A C7A 120.8(9) . . ? C8A C7A C6A 120.9(9) . . ? C7A C8A C8AA 119.2(9) . . ? C4AA C8AA N9A 119.9(7) . . ? C4AA C8AA C8A 120.1(8) . . ? N9A C8AA C8A 120.0(7) . . ? C9AA N9A C8AA 116.9(6) . . ? C9AA N9A C9A 121.9(7) . . ? C8AA N9A C9A 121.2(7) . . ? O1A C9AA N9A 117.1(7) . . ? O1A C9AA C3AA 117.0(7) . . ? N9A C9AA C3AA 125.9(8) . . ? C4A O4A C4'A 122.5(7) . . ? O1'A C1'A C2'A 111.4(9) . . ? O1'A C1'A C3'A 106.1(7) . . ? C2'A C1'A C3'A 111.4(8) . . ? O1'A C1'A C2A 109.7(7) . . ? C2'A C1'A C2A 111.5(7) . . ? C3'A C1'A C2A 106.4(7) . . ? O5A Cl1A O6A 110.4(9) . . ? O5A Cl1A O7A 108.7(8) . . ? O6A Cl1A O7A 113.3(8) . . ? O5A Cl1A O8A 105.7(10) . . ? O6A Cl1A O8A 108.0(7) . . ? O7A Cl1A O8A 110.5(7) . . ? C9AB O1B C2B 108.8(6) . . ? O1B C2B C1'B 107.4(6) . . ? O1B C2B C3B 105.4(6) . . ? C1'B C2B C3B 115.7(7) . . ? C2B C3B C3AB 104.1(6) . . ? C4B C3AB C9AB 119.0(8) . . ? C4B C3AB C3B 135.6(7) . . ? C9AB C3AB C3B 105.3(7) . . ? O4B C4B C3AB 128.8(8) . . ? O4B C4B C4AB 113.8(7) . . ? C3AB C4B C4AB 117.4(8) . . ? C8AB C4AB C5B 117.3(8) . . ? C8AB C4AB C4B 121.1(7) . . ? C5B C4AB C4B 121.6(9) . . ? C6B C5B C4AB 121.5(10) . . ? C5B C6B C7B 120.8(10) . . ? C8B C7B C6B 119.0(10) . . ? C7B C8B C8AB 121.4(10) . . ? N9B C8AB C4AB 120.8(7) . . ? N9B C8AB C8B 119.3(9) . . ? C4AB C8AB C8B 119.9(8) . . ? C9AB N9B C8AB 115.9(7) . . ? C9AB N9B C9B 120.8(7) . . ? C8AB N9B C9B 123.0(7) . . ? O1B C9AB N9B 118.4(7) . . ? O1B C9AB C3AB 115.9(7) . . ? N9B C9AB C3AB 125.7(7) . . ? C4B O4B C4'B 119.8(7) . . ? O1'B C1'B C2'B 110.3(8) . . ? O1'B C1'B C3'B 105.0(6) . . ? C2'B C1'B C3'B 113.6(8) . . ? O1'B C1'B C2B 109.9(7) . . ? C2'B C1'B C2B 110.6(7) . . ? C3'B C1'B C2B 107.4(7) . . ? O6B Cl1B O5B 111.3(14) . . ? O6B Cl1B O8B 122.7(15) . . ? O5B Cl1B O8B 109.1(12) . . ? O6B Cl1B O7B 104.6(11) . . ? O5B Cl1B O7B 105.2(11) . . ? O8B Cl1B O7B 102.1(8) . . ? 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 C9AA O1A C2A C3A 6.7(8) . . . . ? C9AA O1A C2A C1'A 130.2(7) . . . . ? O1A C2A C3A C3AA -7.7(9) . . . . ? C1'A C2A C3A C3AA -125.5(8) . . . . ? C2A C3A C3AA C4A -178.2(9) . . . . ? C2A C3A C3AA C9AA 6.0(9) . . . . ? C9AA C3AA C4A O4A 179.7(8) . . . . ? C3A C3AA C4A O4A 4.3(16) . . . . ? C9AA C3AA C4A C4AA -0.9(11) . . . . ? C3A C3AA C4A C4AA -176.3(9) . . . . ? O4A C4A C4AA C8AA 178.8(8) . . . . ? C3AA C4A C4AA C8AA -0.6(11) . . . . ? O4A C4A C4AA C5A -1.5(11) . . . . ? C3AA C4A C4AA C5A 179.0(8) . . . . ? C8AA C4AA C5A C6A -1.3(14) . . . . ? C4A C4AA C5A C6A 179.0(9) . . . . ? C4AA C5A C6A C7A 1.2(17) . . . . ? C5A C6A C7A C8A -1.0(18) . . . . ? C6A C7A C8A C8AA 0.9(16) . . . . ? C5A C4AA C8AA N9A -178.1(8) . . . . ? C4A C4AA C8AA N9A 1.5(12) . . . . ? C5A C4AA C8AA C8A 1.2(12) . . . . ? C4A C4AA C8AA C8A -179.1(8) . . . . ? C7A C8A C8AA C4AA -1.0(13) . . . . ? C7A C8A C8AA N9A 178.3(9) . . . . ? C4AA C8AA N9A C9AA -0.8(11) . . . . ? C8A C8AA N9A C9AA 179.8(7) . . . . ? C4AA C8AA N9A C9A 176.9(8) . . . . ? C8A C8AA N9A C9A -2.4(12) . . . . ? C2A O1A C9AA N9A 176.7(7) . . . . ? C2A O1A C9AA C3AA -3.0(9) . . . . ? C8AA N9A C9AA O1A 179.6(7) . . . . ? C9A N9A C9AA O1A 1.9(12) . . . . ? C8AA N9A C9AA C3AA -0.8(12) . . . . ? C9A N9A C9AA C3AA -178.5(9) . . . . ? C4A C3AA C9AA O1A -178.7(7) . . . . ? C3A C3AA C9AA O1A -2.0(10) . . . . ? C4A C3AA C9AA N9A 1.7(13) . . . . ? C3A C3AA C9AA N9A 178.3(8) . . . . ? C3AA C4A O4A C4'A -0.4(14) . . . . ? C4AA C4A O4A C4'A -179.8(8) . . . . ? O1A C2A C1'A O1'A -71.4(8) . . . . ? C3A C2A C1'A O1'A 46.9(10) . . . . ? O1A C2A C1'A C2'A 52.5(10) . . . . ? C3A C2A C1'A C2'A 170.8(9) . . . . ? O1A C2A C1'A C3'A 174.3(7) . . . . ? C3A C2A C1'A C3'A -67.5(10) . . . . ? C9AB O1B C2B C1'B 129.9(7) . . . . ? C9AB O1B C2B C3B 5.9(8) . . . . ? O1B C2B C3B C3AB -7.0(9) . . . . ? C1'B C2B C3B C3AB -125.5(7) . . . . ? C2B C3B C3AB C4B -176.8(9) . . . . ? C2B C3B C3AB C9AB 5.8(9) . . . . ? C9AB C3AB C4B O4B -179.7(8) . . . . ? C3B C3AB C4B O4B 3.1(16) . . . . ? C9AB C3AB C4B C4AB 1.0(11) . . . . ? C3B C3AB C4B C4AB -176.2(9) . . . . ? O4B C4B C4AB C8AB 178.8(8) . . . . ? C3AB C4B C4AB C8AB -1.8(12) . . . . ? O4B C4B C4AB C5B -1.2(12) . . . . ? C3AB C4B C4AB C5B 178.2(8) . . . . ? C8AB C4AB C5B C6B -2.5(14) . . . . ? C4B C4AB C5B C6B 177.6(9) . . . . ? C4AB C5B C6B C7B 4.5(17) . . . . ? C5B C6B C7B C8B -2.9(18) . . . . ? C6B C7B C8B C8AB -0.6(16) . . . . ? C5B C4AB C8AB N9B -180.0(8) . . . . ? C4B C4AB C8AB N9B 0.0(12) . . . . ? C5B C4AB C8AB C8B -1.0(12) . . . . ? C4B C4AB C8AB C8B 179.0(7) . . . . ? C7B C8B C8AB N9B -178.5(9) . . . . ? C7B C8B C8AB C4AB 2.5(13) . . . . ? C4AB C8AB N9B C9AB 2.5(11) . . . . ? C8B C8AB N9B C9AB -176.5(7) . . . . ? C4AB C8AB N9B C9B 177.1(8) . . . . ? C8B C8AB N9B C9B -1.9(12) . . . . ? C2B O1B C9AB N9B 175.8(7) . . . . ? C2B O1B C9AB C3AB -2.3(9) . . . . ? C8AB N9B C9AB O1B 178.7(7) . . . . ? C9B N9B C9AB O1B 4.0(11) . . . . ? C8AB N9B C9AB C3AB -3.4(11) . . . . ? C9B N9B C9AB C3AB -178.1(9) . . . . ? C4B C3AB C9AB O1B 179.7(7) . . . . ? C3B C3AB C9AB O1B -2.4(10) . . . . ? C4B C3AB C9AB N9B 1.7(12) . . . . ? C3B C3AB C9AB N9B 179.7(7) . . . . ? C3AB C4B O4B C4'B 8.0(14) . . . . ? C4AB C4B O4B C4'B -172.8(8) . . . . ? O1B C2B C1'B O1'B -71.3(8) . . . . ? C3B C2B C1'B O1'B 46.0(10) . . . . ? O1B C2B C1'B C2'B 50.6(10) . . . . ? C3B C2B C1'B C2'B 168.0(8) . . . . ? O1B C2B C1'B C3'B 175.0(7) . . . . ? C3B C2B C1'B C3'B -67.6(9) . . . . ? _diffrn_measured_fraction_theta_max 1.000 _diffrn_reflns_theta_full 55.00 _diffrn_measured_fraction_theta_full 1.000 _refine_diff_density_max 0.439 _refine_diff_density_min -0.275 _refine_diff_density_rms 0.071 data_bar2 _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C25 H29 N O6' _chemical_formula_weight 439.49 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' _symmetry_cell_setting Monoclinic _symmetry_space_group_name_H-M P2(1) loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y+1/2, -z' _cell_length_a 8.120(21) _cell_length_b 12.457(19) _cell_length_c 12.139(19) _cell_angle_alpha 90.00 _cell_angle_beta 101.18(17) _cell_angle_gamma 90.00 _cell_volume 1205(4) _cell_formula_units_Z 2 _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 0.54 _exptl_crystal_size_mid 0.30 _exptl_crystal_size_min 0.16 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.212 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 468 _exptl_absorpt_coefficient_mu 0.086 _exptl_absorpt_correction_type ? _exptl_absorpt_correction_T_min 0.9548 _exptl_absorpt_correction_T_max 0.9863 _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 293(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 ? _diffrn_measurement_method ? _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 2313 _diffrn_reflns_av_R_equivalents 0.1598 _diffrn_reflns_av_sigmaI/netI 0.1421 _diffrn_reflns_limit_h_min -8 _diffrn_reflns_limit_h_max 9 _diffrn_reflns_limit_k_min 0 _diffrn_reflns_limit_k_max 14 _diffrn_reflns_limit_l_min 0 _diffrn_reflns_limit_l_max 14 _diffrn_reflns_theta_min 1.71 _diffrn_reflns_theta_max 25.07 _reflns_number_total 2210 _reflns_number_gt 985 _reflns_threshold_expression >2sigma(I) _computing_data_collection ? _computing_cell_refinement ? _computing_data_reduction ? _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 _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.1900P)^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 0.033(12) _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 -4(6) _refine_ls_number_reflns 2210 _refine_ls_number_parameters 296 _refine_ls_number_restraints 1 _refine_ls_R_factor_all 0.2036 _refine_ls_R_factor_gt 0.1013 _refine_ls_wR_factor_ref 0.3195 _refine_ls_wR_factor_gt 0.2435 _refine_ls_goodness_of_fit_ref 0.945 _refine_ls_restrained_S_all 0.945 _refine_ls_shift/su_max 0.124 _refine_ls_shift/su_mean 0.004 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_multiplicit _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group O1 O -0.2506(10) -0.9824(8) -0.0305(6) 0.058(2) Uani 1 1 d . . . C2 C -0.2569(17) -1.0598(12) -0.1219(10) 0.060(4) Uani 1 1 d . . . C3 C -0.4361(18) -1.0691(10) -0.1903(10) 0.059(4) Uani 1 1 d . . . H3 H -0.4393 -1.1207 -0.2517 0.070 Uiso 1 1 calc R . . O3 O -0.4822(13) -0.9639(8) -0.2349(6) 0.076(3) Uani 1 1 d . . . C4 C -0.5584(17) -1.1014(12) -0.1186(10) 0.065(4) Uani 1 1 d . . . H4A H -0.5484 -1.1777 -0.1030 0.078 Uiso 1 1 calc R . . H4B H -0.6720 -1.0870 -0.1581 0.078 Uiso 1 1 calc R . . C4A C -0.5230(17) -1.0390(12) -0.0097(10) 0.057(4) Uani 1 1 d . . . C5 C -0.6606(18) -1.0332(12) 0.0552(10) 0.057(4) Uani 1 1 d . . . O5 O -0.7857(13) -1.0835(11) 0.0335(10) 0.096(4) Uani 1 1 d . . . N6 N -0.6220(13) -0.9718(10) 0.1560(9) 0.059(3) Uani 1 1 d . . . C6 C -0.760(2) -0.9711(17) 0.2213(13) 0.097(6) Uani 1 1 d . . . H6A H -0.7192 -0.9405 0.2941 0.145 Uiso 1 1 calc R . . H6B H -0.7966 -1.0433 0.2297 0.145 Uiso 1 1 calc R . . H6C H -0.8518 -0.9291 0.1822 0.145 Uiso 1 1 calc R . . C6A C -0.4775(14) -0.9159(10) 0.1905(9) 0.044(3) Uani 1 1 d . . . C7 C -0.449(2) -0.8573(13) 0.2912(10) 0.069(4) Uani 1 1 d . . . H7 H -0.5306 -0.8559 0.3353 0.083 Uiso 1 1 calc R . . C8 C -0.300(2) -0.8012(13) 0.3254(12) 0.073(4) Uani 1 1 d . . . H8 H -0.2825 -0.7615 0.3915 0.088 Uiso 1 1 calc R . . C9 C -0.1760(19) -0.8048(13) 0.2600(11) 0.071(4) Uani 1 1 d . . . H9 H -0.0761 -0.7675 0.2832 0.086 Uiso 1 1 calc R . . C10 C -0.1994(15) -0.8617(11) 0.1637(9) 0.054(3) Uani 1 1 d . . . H10 H -0.1151 -0.8635 0.1217 0.064 Uiso 1 1 calc R . . C10A C -0.3510(15) -0.9189(10) 0.1257(9) 0.046(3) Uani 1 1 d . . . C10B C -0.3818(15) -0.9809(10) 0.0233(10) 0.048(3) Uani 1 1 d . . . C11 C -0.1935(18) -1.1697(13) -0.0735(12) 0.075(5) Uani 1 1 d . . . H11A H -0.0881 -1.1608 -0.0226 0.113 Uiso 1 1 calc R . . H11B H -0.1789 -1.2166 -0.1336 0.113 Uiso 1 1 calc R . . H11C H -0.2740 -1.2002 -0.0341 0.113 Uiso 1 1 calc R . . C12 C -0.1337(19) -1.0157(16) -0.1874(11) 0.087(5) Uani 1 1 d . . . H12A H -0.1748 -0.9488 -0.2212 0.130 Uiso 1 1 calc R . . H12B H -0.1197 -1.0658 -0.2449 0.130 Uiso 1 1 calc R . . H12C H -0.0276 -1.0042 -0.1379 0.130 Uiso 1 1 calc R . . C13 C -0.5549(18) -0.9536(13) -0.3435(10) 0.068(4) Uani 1 1 d . . . O13 O -0.5831(19) -1.0311(11) -0.4030(8) 0.118(5) Uani 1 1 d . . . C14 C -0.6034(16) -0.8409(12) -0.3710(8) 0.050(3) Uani 1 1 d . . . O14 O -0.6473(12) -0.8330(8) -0.4948(6) 0.063(3) Uani 1 1 d . . . C15 C -0.7370(17) -0.7418(12) -0.5165(10) 0.060(4) Uani 1 1 d . . . O15 O -0.7894(14) -0.7144(10) -0.6134(7) 0.087(3) Uani 1 1 d . . . C16 C -0.754(2) -0.6930(13) -0.4061(11) 0.072(4) Uani 1 1 d . . . C17 C -0.578(3) -0.6532(14) -0.3613(14) 0.103(7) Uani 1 1 d . . . H17A H -0.5735 -0.6111 -0.2936 0.124 Uiso 1 1 calc R . . H17B H -0.5378 -0.6094 -0.4169 0.124 Uiso 1 1 calc R . . C18 C -0.473(2) -0.7549(14) -0.3365(14) 0.090(5) Uani 1 1 d . . . H18A H -0.3855 -0.7582 -0.3808 0.108 Uiso 1 1 calc R . . H18B H -0.4221 -0.7603 -0.2575 0.108 Uiso 1 1 calc R . . C19 C -0.761(2) -0.7966(12) -0.3385(11) 0.068(4) Uani 1 1 d . . . C20 C -0.917(2) -0.8617(19) -0.3821(14) 0.101(6) Uani 1 1 d . . . H20A H -0.9339 -0.8668 -0.4624 0.152 Uiso 1 1 calc R . . H20B H -1.0126 -0.8271 -0.3615 0.152 Uiso 1 1 calc R . . H20C H -0.9048 -0.9323 -0.3500 0.152 Uiso 1 1 calc R . . C21 C -0.739(3) -0.776(2) -0.2082(11) 0.138(9) Uani 1 1 d . . . H21A H -0.7542 -0.8423 -0.1710 0.207 Uiso 1 1 calc R . . H21B H -0.8207 -0.7248 -0.1945 0.207 Uiso 1 1 calc R . . H21C H -0.6281 -0.7488 -0.1797 0.207 Uiso 1 1 calc R . . C22 C -0.894(4) -0.611(2) -0.414(2) 0.160(11) Uani 1 1 d . . . H22A H -0.8871 -0.5763 -0.3427 0.240 Uiso 1 1 calc R . . H22B H -1.0005 -0.6459 -0.4351 0.240 Uiso 1 1 calc R . . H22C H -0.8821 -0.5581 -0.4698 0.240 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 O1 0.054(5) 0.086(7) 0.034(4) -0.015(4) 0.006(4) -0.015(5) C2 0.071(9) 0.073(10) 0.034(6) -0.011(7) 0.005(6) 0.009(8) C3 0.098(11) 0.037(7) 0.039(7) 0.004(6) 0.008(7) -0.001(7) O3 0.106(7) 0.077(7) 0.033(4) -0.002(5) -0.014(5) -0.024(6) C4 0.076(10) 0.067(9) 0.044(7) -0.004(7) -0.008(7) -0.001(8) C4A 0.058(8) 0.075(10) 0.036(6) 0.017(7) 0.003(6) -0.004(8) C5 0.059(9) 0.068(9) 0.043(7) 0.010(7) 0.005(6) -0.006(8) O5 0.057(7) 0.135(10) 0.092(8) -0.006(7) 0.004(6) -0.041(7) N6 0.044(6) 0.077(8) 0.057(6) 0.007(6) 0.014(5) 0.010(6) C6 0.098(12) 0.127(16) 0.078(10) 0.029(11) 0.049(9) 0.016(12) C6A 0.042(7) 0.052(7) 0.036(6) 0.004(6) 0.003(5) 0.016(6) C7 0.093(11) 0.085(11) 0.036(7) 0.003(8) 0.024(7) 0.019(10) C8 0.091(11) 0.073(10) 0.050(8) -0.009(8) -0.003(8) 0.008(10) C9 0.075(10) 0.076(10) 0.051(8) -0.012(8) -0.017(7) 0.002(9) C10 0.050(7) 0.073(9) 0.036(6) -0.008(7) 0.005(6) -0.001(7) C10A 0.052(7) 0.057(8) 0.029(6) 0.002(5) 0.008(5) 0.009(7) C10B 0.053(7) 0.044(7) 0.047(7) 0.012(6) 0.014(6) -0.012(6) C11 0.061(9) 0.095(12) 0.068(9) 0.003(9) 0.009(7) 0.022(9) C12 0.090(11) 0.125(15) 0.053(8) -0.001(9) 0.032(8) 0.000(11) C13 0.087(10) 0.093(12) 0.019(6) -0.024(7) 0.002(6) 0.000(9) O13 0.197(14) 0.104(10) 0.040(6) -0.007(7) -0.012(7) 0.030(9) C14 0.065(8) 0.067(9) 0.016(5) -0.006(5) 0.003(5) -0.005(7) O14 0.084(6) 0.078(7) 0.026(4) 0.003(4) 0.011(4) 0.000(6) C15 0.066(9) 0.076(11) 0.038(7) 0.015(7) 0.008(6) -0.008(8) O15 0.108(8) 0.110(9) 0.033(5) 0.015(5) -0.010(5) -0.006(7) C16 0.109(12) 0.065(10) 0.048(8) -0.004(7) 0.031(8) -0.008(9) C17 0.157(18) 0.059(11) 0.077(12) 0.012(9) -0.019(11) -0.039(12) C18 0.107(14) 0.077(11) 0.086(11) 0.011(9) 0.015(10) -0.028(11) C19 0.094(11) 0.071(10) 0.044(7) -0.004(7) 0.030(7) 0.009(9) C20 0.081(11) 0.152(17) 0.083(11) 0.012(12) 0.043(9) -0.017(12) C21 0.22(2) 0.17(2) 0.029(7) -0.020(11) 0.040(11) 0.046(19) C22 0.24(3) 0.120(18) 0.117(17) -0.012(14) 0.039(18) 0.09(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 O1 C10B 1.354(14) . ? O1 C2 1.463(15) . ? C2 C12 1.498(19) . ? C2 C3 1.534(19) . ? C2 C11 1.54(2) . ? C3 O3 1.440(15) . ? C3 C4 1.497(19) . ? O3 C13 1.341(14) . ? C4 C4A 1.512(18) . ? C4A C10B 1.349(17) . ? C4A C5 1.49(2) . ? C5 O5 1.179(15) . ? C5 N6 1.426(17) . ? N6 C6A 1.358(16) . ? N6 C6 1.491(17) . ? C6A C10A 1.411(16) . ? C6A C7 1.404(17) . ? C7 C8 1.39(2) . ? C8 C9 1.40(2) . ? C9 C10 1.348(17) . ? C10 C10A 1.420(17) . ? C10A C10B 1.443(16) . ? C13 O13 1.201(17) . ? C13 C14 1.48(2) . ? C14 O14 1.479(12) . ? C14 C19 1.512(19) . ? C14 C18 1.51(2) . ? O14 C15 1.347(17) . ? C15 O15 1.220(14) . ? C15 C16 1.504(18) . ? C16 C17 1.52(2) . ? C16 C19 1.53(2) . ? C16 C22 1.52(3) . ? C17 C18 1.52(3) . ? C19 C20 1.51(2) . ? C19 C21 1.578(18) . ? 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 C10B O1 C2 117.4(10) . . ? O1 C2 C12 103.4(12) . . ? O1 C2 C3 110.5(11) . . ? C12 C2 C3 113.7(11) . . ? O1 C2 C11 109.7(10) . . ? C12 C2 C11 108.7(13) . . ? C3 C2 C11 110.6(12) . . ? O3 C3 C4 108.0(12) . . ? O3 C3 C2 106.6(11) . . ? C4 C3 C2 111.8(10) . . ? C13 O3 C3 119.2(11) . . ? C3 C4 C4A 109.6(11) . . ? C10B C4A C5 119.9(12) . . ? C10B C4A C4 122.8(11) . . ? C5 C4A C4 116.9(12) . . ? O5 C5 N6 120.9(13) . . ? O5 C5 C4A 123.9(13) . . ? N6 C5 C4A 114.7(12) . . ? C6A N6 C5 124.9(11) . . ? C6A N6 C6 121.7(12) . . ? C5 N6 C6 113.4(12) . . ? N6 C6A C10A 119.6(11) . . ? N6 C6A C7 121.4(12) . . ? C10A C6A C7 119.0(12) . . ? C6A C7 C8 120.6(13) . . ? C7 C8 C9 119.7(13) . . ? C10 C9 C8 120.9(14) . . ? C9 C10 C10A 120.9(12) . . ? C6A C10A C10 119.0(10) . . ? C6A C10A C10B 118.1(11) . . ? C10 C10A C10B 122.9(10) . . ? O1 C10B C4A 123.5(11) . . ? O1 C10B C10A 113.7(10) . . ? C4A C10B C10A 122.6(11) . . ? O13 C13 O3 120.7(15) . . ? O13 C13 C14 128.0(12) . . ? O3 C13 C14 111.1(11) . . ? C13 C14 O14 107.1(10) . . ? C13 C14 C19 119.3(11) . . ? O14 C14 C19 101.0(9) . . ? C13 C14 C18 118.0(12) . . ? O14 C14 C18 104.6(11) . . ? C19 C14 C18 104.6(13) . . ? C15 O14 C14 105.6(10) . . ? O15 C15 O14 119.9(13) . . ? O15 C15 C16 132.2(15) . . ? O14 C15 C16 107.9(11) . . ? C17 C16 C15 101.8(13) . . ? C17 C16 C19 102.2(13) . . ? C15 C16 C19 98.9(12) . . ? C17 C16 C22 116.4(18) . . ? C15 C16 C22 114.5(14) . . ? C19 C16 C22 120.1(16) . . ? C16 C17 C18 104.7(13) . . ? C14 C18 C17 101.5(14) . . ? C14 C19 C20 114.1(13) . . ? C14 C19 C16 92.9(11) . . ? C20 C19 C16 112.1(13) . . ? C14 C19 C21 112.5(13) . . ? C20 C19 C21 111.1(14) . . ? C16 C19 C21 113.0(14) . . ? 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 C10B O1 C2 C12 160.4(11) . . . . ? C10B O1 C2 C3 38.4(15) . . . . ? C10B O1 C2 C11 -83.8(14) . . . . ? O1 C2 C3 O3 60.1(14) . . . . ? C12 C2 C3 O3 -55.6(15) . . . . ? C11 C2 C3 O3 -178.2(11) . . . . ? O1 C2 C3 C4 -57.7(14) . . . . ? C12 C2 C3 C4 -173.4(13) . . . . ? C11 C2 C3 C4 64.0(14) . . . . ? C4 C3 O3 C13 -106.1(13) . . . . ? C2 C3 O3 C13 133.6(12) . . . . ? O3 C3 C4 C4A -73.7(13) . . . . ? C2 C3 C4 C4A 43.3(15) . . . . ? C3 C4 C4A C10B -12.1(18) . . . . ? C3 C4 C4A C5 160.9(11) . . . . ? C10B C4A C5 O5 -178.0(13) . . . . ? C4 C4A C5 O5 9(2) . . . . ? C10B C4A C5 N6 -5.6(17) . . . . ? C4 C4A C5 N6 -178.8(11) . . . . ? O5 C5 N6 C6A 176.6(13) . . . . ? C4A C5 N6 C6A 4.0(18) . . . . ? O5 C5 N6 C6 -5.1(19) . . . . ? C4A C5 N6 C6 -177.7(12) . . . . ? C5 N6 C6A C10A -1.7(17) . . . . ? C6 N6 C6A C10A -179.9(13) . . . . ? C5 N6 C6A C7 -180.0(12) . . . . ? C6 N6 C6A C7 1.9(18) . . . . ? N6 C6A C7 C8 179.6(13) . . . . ? C10A C6A C7 C8 1.3(19) . . . . ? C6A C7 C8 C9 -1(2) . . . . ? C7 C8 C9 C10 0(2) . . . . ? C8 C9 C10 C10A 0(2) . . . . ? N6 C6A C10A C10 -178.9(11) . . . . ? C7 C6A C10A C10 -0.6(17) . . . . ? N6 C6A C10A C10B 0.9(16) . . . . ? C7 C6A C10A C10B 179.1(11) . . . . ? C9 C10 C10A C6A -0.2(18) . . . . ? C9 C10 C10A C10B -180.0(12) . . . . ? C2 O1 C10B C4A -6.6(17) . . . . ? C2 O1 C10B C10A 168.0(10) . . . . ? C5 C4A C10B O1 179.4(12) . . . . ? C4 C4A C10B O1 -7.8(19) . . . . ? C5 C4A C10B C10A 5.3(18) . . . . ? C4 C4A C10B C10A 178.1(12) . . . . ? C6A C10A C10B O1 -177.5(10) . . . . ? C10 C10A C10B O1 2.3(16) . . . . ? C6A C10A C10B C4A -2.8(17) . . . . ? C10 C10A C10B C4A 176.9(12) . . . . ? C3 O3 C13 O13 1(2) . . . . ? C3 O3 C13 C14 176.0(12) . . . . ? O13 C13 C14 O14 -17(2) . . . . ? O3 C13 C14 O14 167.9(10) . . . . ? O13 C13 C14 C19 96.5(19) . . . . ? O3 C13 C14 C19 -78.4(14) . . . . ? O13 C13 C14 C18 -134.8(18) . . . . ? O3 C13 C14 C18 50.4(16) . . . . ? C13 C14 O14 C15 162.0(11) . . . . ? C19 C14 O14 C15 36.5(13) . . . . ? C18 C14 O14 C15 -72.0(13) . . . . ? C14 O14 C15 O15 179.6(12) . . . . ? C14 O14 C15 C16 -1.6(14) . . . . ? O15 C15 C16 C17 -109.8(18) . . . . ? O14 C15 C16 C17 71.5(14) . . . . ? O15 C15 C16 C19 145.6(17) . . . . ? O14 C15 C16 C19 -33.0(14) . . . . ? O15 C15 C16 C22 17(3) . . . . ? O14 C15 C16 C22 -162.0(18) . . . . ? C15 C16 C17 C18 -67.8(15) . . . . ? C19 C16 C17 C18 34.1(16) . . . . ? C22 C16 C17 C18 167.0(16) . . . . ? C13 C14 C18 C17 -171.0(12) . . . . ? O14 C14 C18 C17 70.2(14) . . . . ? C19 C14 C18 C17 -35.7(15) . . . . ? C16 C17 C18 C14 0.3(16) . . . . ? C13 C14 C19 C20 -54.7(15) . . . . ? O14 C14 C19 C20 62.2(14) . . . . ? C18 C14 C19 C20 170.7(13) . . . . ? C13 C14 C19 C16 -170.5(10) . . . . ? O14 C14 C19 C16 -53.6(12) . . . . ? C18 C14 C19 C16 54.9(12) . . . . ? C13 C14 C19 C21 73.1(18) . . . . ? O14 C14 C19 C21 -170.0(14) . . . . ? C18 C14 C19 C21 -61.5(17) . . . . ? C17 C16 C19 C14 -53.1(13) . . . . ? C15 C16 C19 C14 51.2(12) . . . . ? C22 C16 C19 C14 176.3(16) . . . . ? C17 C16 C19 C20 -170.5(14) . . . . ? C15 C16 C19 C20 -66.3(15) . . . . ? C22 C16 C19 C20 59(2) . . . . ? C17 C16 C19 C21 63.0(18) . . . . ? C15 C16 C19 C21 167.2(14) . . . . ? C22 C16 C19 C21 -68(2) . . . . ? _diffrn_measured_fraction_theta_max 0.982 _diffrn_reflns_theta_full 25.07 _diffrn_measured_fraction_theta_full 0.982 _refine_diff_density_max 0.443 _refine_diff_density_min -0.315 _refine_diff_density_rms 0.081 data_jocqin _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C25 H23 Br F3 N O5' _chemical_formula_weight 554.35 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' 'O' 'O' 0.0106 0.0060 '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' 'F' 'F' 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 'Br' 'Br' -0.2901 2.4595 '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+1/2, -y+1/2, -z' '-x, y+1/2, -z+1/2' _cell_length_a 10.330(3) _cell_length_b 11.287(4) _cell_length_c 21.203(6) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 2472.2(13) _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 ? _exptl_crystal_size_mid ? _exptl_crystal_size_min ? _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.489 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1128 _exptl_absorpt_coefficient_mu 1.721 _exptl_absorpt_correction_type ? _exptl_absorpt_correction_T_min ? _exptl_absorpt_correction_T_max ? _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 293(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 ? _diffrn_measurement_method ? _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 3221 _diffrn_reflns_av_R_equivalents 0.0000 _diffrn_reflns_av_sigmaI/netI 0.1174 _diffrn_reflns_limit_h_min 0 _diffrn_reflns_limit_h_max 13 _diffrn_reflns_limit_k_min 0 _diffrn_reflns_limit_k_max 14 _diffrn_reflns_limit_l_min 0 _diffrn_reflns_limit_l_max 27 _diffrn_reflns_theta_min 1.92 _diffrn_reflns_theta_max 27.56 _reflns_number_total 3221 _reflns_number_gt 1461 _reflns_threshold_expression >2sigma(I) _computing_data_collection ? _computing_cell_refinement ? _computing_data_reduction ? _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 _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0738P)^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 none _refine_ls_extinction_coef ? _refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881' _refine_ls_abs_structure_Flack -0.03(2) _refine_ls_number_reflns 3221 _refine_ls_number_parameters 320 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.1472 _refine_ls_R_factor_gt 0.0685 _refine_ls_wR_factor_ref 0.1526 _refine_ls_wR_factor_gt 0.1280 _refine_ls_goodness_of_fit_ref 0.896 _refine_ls_restrained_S_all 0.896 _refine_ls_shift/su_max 0.007 _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_multiplicit _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group Br1 Br 0.13911(8) 0.85925(10) 0.13290(6) 0.0760(4) Uani 1 1 d . . . F1 F -0.5959(5) 0.6202(5) 0.1557(3) 0.0867(19) Uani 1 1 d . . . F2 F -0.4013(6) 0.5566(5) 0.1654(3) 0.081(2) Uani 1 1 d . . . F3 F -0.4655(5) 0.6314(6) 0.0780(3) 0.0878(19) Uani 1 1 d . . . O1 O 0.0320(5) 1.1109(5) 0.1897(3) 0.0531(16) Uani 1 1 d . . . O2 O -0.2506(5) 0.8951(5) 0.1548(3) 0.0392(15) Uani 1 1 d . . . O3 O -0.2238(6) 0.7125(6) 0.1151(4) 0.075(2) Uani 1 1 d . . . O4 O -0.5175(5) 0.8407(6) 0.1326(3) 0.0593(16) Uani 1 1 d . . . O5 O -0.2808(6) 1.0125(6) 0.0331(3) 0.0541(16) Uani 1 1 d . . . C2 C 0.0020(9) 1.0032(9) 0.2249(5) 0.056(3) Uani 1 1 d . . . C3 C -0.0188(7) 0.9004(8) 0.1787(4) 0.047(2) Uani 1 1 d . . . H3 H -0.0467 0.8309 0.2028 0.056 Uiso 1 1 calc R . . C4 C -0.1210(7) 0.9263(7) 0.1282(4) 0.042(2) Uani 1 1 d . . . H4 H -0.1038 0.8787 0.0905 0.050 Uiso 1 1 calc R . . C4A C -0.1263(8) 1.0545(7) 0.1112(3) 0.0363(19) Uani 1 1 d . . . C5 C -0.2014(8) 1.0928(8) 0.0616(4) 0.041(2) Uani 1 1 d . . . C5A C -0.2054(8) 1.2140(8) 0.0451(4) 0.042(2) Uani 1 1 d . . . C6 C -0.2915(9) 1.2635(10) 0.0010(5) 0.056(3) Uani 1 1 d . . . H6 H -0.3509 1.2148 -0.0194 0.067 Uiso 1 1 calc R . . C7 C -0.2893(11) 1.3828(9) -0.0127(5) 0.074(3) Uani 1 1 d . . . H7 H -0.3467 1.4145 -0.0420 0.089 Uiso 1 1 calc R . . C8 C -0.2009(12) 1.4546(10) 0.0176(5) 0.073(3) Uani 1 1 d . . . H8 H -0.1982 1.5348 0.0076 0.088 Uiso 1 1 calc R . . C9 C -0.1177(11) 1.4115(9) 0.0616(5) 0.062(3) Uani 1 1 d . . . H9 H -0.0605 1.4624 0.0820 0.074 Uiso 1 1 calc R . . C9A C -0.1180(9) 1.2895(7) 0.0765(4) 0.042(2) Uani 1 1 d . . . N10 N -0.0383(6) 1.2518(6) 0.1250(4) 0.0490(19) Uani 1 1 d . . . C10A C -0.0471(7) 1.1417(8) 0.1403(4) 0.0411(19) Uani 1 1 d . . . C11 C -0.2503(12) 0.9764(12) -0.0290(5) 0.094(4) Uani 1 1 d . . . H11A H -0.2305 1.0447 -0.0542 0.140 Uiso 1 1 calc R . . H11B H -0.3229 0.9354 -0.0469 0.140 Uiso 1 1 calc R . . H11C H -0.1767 0.9245 -0.0281 0.140 Uiso 1 1 calc R . . C12 C -0.2901(8) 0.7850(8) 0.1406(4) 0.043(2) Uani 1 1 d . . . C13 C -0.4308(8) 0.7636(7) 0.1645(4) 0.036(2) Uani 1 1 d . . . C14 C -0.4735(8) 0.6418(10) 0.1405(5) 0.061(3) Uani 1 1 d . . . C15 C -0.4392(7) 0.7667(6) 0.2352(4) 0.038(2) Uani 1 1 d . . . C16 C -0.5577(8) 0.7853(7) 0.2647(5) 0.057(3) Uani 1 1 d . . . H16 H -0.6319 0.7971 0.2406 0.068 Uiso 1 1 calc R . . C17 C -0.5649(11) 0.7863(9) 0.3286(6) 0.071(3) Uani 1 1 d . . . H17 H -0.6448 0.8001 0.3475 0.085 Uiso 1 1 calc R . . C18 C -0.4581(12) 0.7678(9) 0.3668(6) 0.077(3) Uani 1 1 d . . . H18 H -0.4653 0.7674 0.4105 0.092 Uiso 1 1 calc R . . C19 C -0.3395(9) 0.7496(9) 0.3372(5) 0.060(3) Uani 1 1 d . . . H19 H -0.2655 0.7377 0.3614 0.072 Uiso 1 1 calc R . . C20 C -0.3308(8) 0.7492(7) 0.2729(4) 0.048(2) Uani 1 1 d . . . H20 H -0.2506 0.7369 0.2540 0.057 Uiso 1 1 calc R . . C21 C 0.1198(10) 0.9838(9) 0.2684(5) 0.086(4) Uani 1 1 d . . . H21A H 0.1966 0.9759 0.2433 0.129 Uiso 1 1 calc R . . H21B H 0.1072 0.9131 0.2928 0.129 Uiso 1 1 calc R . . H21C H 0.1288 1.0504 0.2962 0.129 Uiso 1 1 calc R . . C22 C -0.1190(9) 1.0235(8) 0.2637(4) 0.062(3) Uani 1 1 d . . . H22A H -0.1062 1.0902 0.2911 0.093 Uiso 1 1 calc R . . H22B H -0.1368 0.9543 0.2886 0.093 Uiso 1 1 calc R . . H22C H -0.1908 1.0388 0.2361 0.093 Uiso 1 1 calc R . . C23 C -0.5181(9) 0.9640(9) 0.1474(5) 0.071(3) Uani 1 1 d . . . H23A H -0.5107 0.9741 0.1922 0.106 Uiso 1 1 calc R . . H23B H -0.5976 0.9988 0.1330 0.106 Uiso 1 1 calc R . . H23C H -0.4464 1.0020 0.1269 0.106 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 Br1 0.0361(4) 0.0806(7) 0.1111(9) 0.0182(8) 0.0113(6) 0.0074(6) F1 0.066(4) 0.086(4) 0.108(5) -0.015(4) 0.004(3) -0.037(3) F2 0.084(5) 0.042(3) 0.116(5) -0.006(3) -0.003(4) -0.012(3) F3 0.089(4) 0.098(5) 0.076(4) -0.033(4) -0.014(3) -0.026(4) O1 0.052(3) 0.045(4) 0.062(4) 0.017(3) -0.026(3) -0.018(3) O2 0.026(3) 0.037(3) 0.055(4) -0.001(3) 0.008(2) -0.007(3) O3 0.058(4) 0.044(4) 0.122(7) -0.028(4) 0.026(4) -0.005(3) O4 0.046(3) 0.050(4) 0.081(4) 0.007(4) -0.010(4) 0.003(3) O5 0.046(3) 0.069(4) 0.047(4) -0.014(3) 0.000(3) -0.007(3) C2 0.049(5) 0.052(6) 0.065(6) 0.012(6) -0.017(5) -0.017(5) C3 0.034(4) 0.043(5) 0.065(6) 0.011(5) 0.007(4) -0.006(4) C4 0.038(4) 0.041(5) 0.046(5) -0.006(4) 0.001(5) -0.011(4) C4A 0.038(4) 0.042(5) 0.029(5) 0.001(4) 0.006(4) -0.014(4) C5 0.041(5) 0.050(6) 0.030(5) 0.003(4) 0.001(4) -0.005(5) C5A 0.031(4) 0.045(6) 0.049(6) 0.000(5) 0.005(4) 0.000(4) C6 0.057(5) 0.070(7) 0.041(5) -0.010(5) -0.001(5) 0.020(6) C7 0.105(8) 0.057(7) 0.062(7) 0.005(6) -0.006(7) 0.037(7) C8 0.119(9) 0.053(7) 0.047(7) 0.006(5) 0.005(7) 0.025(7) C9 0.073(7) 0.056(6) 0.057(7) 0.005(5) -0.001(6) 0.010(6) C9A 0.049(6) 0.042(5) 0.034(5) 0.007(4) 0.006(5) 0.020(5) N10 0.048(4) 0.033(4) 0.065(5) 0.007(4) 0.000(4) -0.009(3) C10A 0.034(4) 0.049(5) 0.040(5) 0.014(5) -0.003(4) -0.009(5) C11 0.094(9) 0.111(10) 0.075(8) -0.044(8) 0.017(7) -0.016(8) C12 0.040(5) 0.042(6) 0.047(6) -0.004(5) -0.007(5) -0.012(4) C13 0.032(4) 0.030(5) 0.047(6) 0.000(4) -0.002(4) 0.000(4) C14 0.048(5) 0.057(6) 0.077(8) -0.007(7) -0.006(6) -0.011(6) C15 0.028(4) 0.021(4) 0.064(6) 0.004(4) 0.002(4) -0.004(4) C16 0.040(5) 0.048(6) 0.083(8) 0.010(6) 0.017(5) 0.004(5) C17 0.064(7) 0.065(7) 0.082(9) 0.022(6) 0.030(7) 0.011(6) C18 0.112(9) 0.066(7) 0.052(7) 0.016(6) 0.024(8) -0.008(7) C19 0.063(7) 0.062(7) 0.054(7) 0.011(5) 0.001(5) -0.012(6) C20 0.047(5) 0.047(6) 0.050(6) 0.013(5) 0.014(5) 0.004(4) C21 0.081(8) 0.073(7) 0.104(9) 0.046(7) -0.042(7) -0.030(7) C22 0.069(6) 0.060(6) 0.058(6) -0.002(5) -0.003(6) -0.013(6) C23 0.055(6) 0.060(7) 0.098(9) 0.020(6) 0.001(6) 0.012(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 Br1 C3 1.954(8) . ? F1 C14 1.328(9) . ? F2 C14 1.326(11) . ? F3 C14 1.333(11) . ? O1 C10A 1.374(9) . ? O1 C2 1.460(10) . ? O2 C12 1.342(10) . ? O2 C4 1.494(8) . ? O3 C12 1.196(10) . ? O4 C13 1.420(9) . ? O4 C23 1.426(11) . ? O5 C5 1.365(10) . ? O5 C11 1.413(11) . ? C2 C22 1.514(13) . ? C2 C3 1.534(13) . ? C2 C21 1.542(12) . ? C3 C4 1.531(11) . ? C4 C4A 1.492(11) . ? C4A C5 1.376(11) . ? C4A C10A 1.421(10) . ? C5 C5A 1.413(11) . ? C5A C9A 1.408(12) . ? C5A C6 1.407(12) . ? C6 C7 1.377(15) . ? C7 C8 1.380(15) . ? C8 C9 1.359(13) . ? C9 C9A 1.413(12) . ? C9A N10 1.385(10) . ? N10 C10A 1.287(10) . ? C12 C13 1.558(11) . ? C13 C15 1.502(11) . ? C13 C14 1.532(13) . ? C15 C16 1.391(10) . ? C15 C20 1.391(10) . ? C16 C17 1.358(13) . ? C17 C18 1.385(15) . ? C18 C19 1.391(13) . ? C19 C20 1.367(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 C10A O1 C2 118.4(6) . . ? C12 O2 C4 113.9(6) . . ? C13 O4 C23 119.8(7) . . ? C5 O5 C11 118.1(7) . . ? O1 C2 C22 109.1(8) . . ? O1 C2 C3 109.4(7) . . ? C22 C2 C3 110.3(7) . . ? O1 C2 C21 104.8(7) . . ? C22 C2 C21 110.3(8) . . ? C3 C2 C21 112.7(8) . . ? C4 C3 C2 113.5(7) . . ? C4 C3 Br1 105.9(6) . . ? C2 C3 Br1 112.4(6) . . ? C4A C4 O2 106.7(6) . . ? C4A C4 C3 112.3(7) . . ? O2 C4 C3 108.1(6) . . ? C5 C4A C10A 116.0(7) . . ? C5 C4A C4 120.7(7) . . ? C10A C4A C4 123.1(7) . . ? O5 C5 C4A 117.9(8) . . ? O5 C5 C5A 121.1(8) . . ? C4A C5 C5A 120.7(8) . . ? C5 C5A C9A 116.8(8) . . ? C5 C5A C6 124.6(9) . . ? C9A C5A C6 118.6(8) . . ? C7 C6 C5A 121.2(10) . . ? C8 C7 C6 119.2(10) . . ? C9 C8 C7 121.9(10) . . ? C8 C9 C9A 120.0(11) . . ? N10 C9A C5A 123.1(8) . . ? N10 C9A C9 117.6(9) . . ? C5A C9A C9 119.1(9) . . ? C10A N10 C9A 116.2(7) . . ? N10 C10A O1 113.2(7) . . ? N10 C10A C4A 126.9(8) . . ? O1 C10A C4A 119.9(7) . . ? O3 C12 O2 124.2(8) . . ? O3 C12 C13 125.1(8) . . ? O2 C12 C13 110.7(8) . . ? O4 C13 C15 115.1(7) . . ? O4 C13 C14 102.2(7) . . ? C15 C13 C14 109.6(7) . . ? O4 C13 C12 109.8(7) . . ? C15 C13 C12 112.0(7) . . ? C14 C13 C12 107.4(7) . . ? F1 C14 F2 107.9(9) . . ? F1 C14 F3 106.5(7) . . ? F2 C14 F3 107.3(9) . . ? F1 C14 C13 111.0(8) . . ? F2 C14 C13 110.9(7) . . ? F3 C14 C13 113.0(9) . . ? C16 C15 C20 118.1(8) . . ? C16 C15 C13 120.2(8) . . ? C20 C15 C13 121.7(7) . . ? C17 C16 C15 119.9(9) . . ? C16 C17 C18 122.6(10) . . ? C17 C18 C19 117.4(10) . . ? C20 C19 C18 120.5(10) . . ? C19 C20 C15 121.4(8) . . ? 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 C10A O1 C2 C22 -71.1(9) . . . . ? C10A O1 C2 C3 49.7(10) . . . . ? C10A O1 C2 C21 170.7(8) . . . . ? O1 C2 C3 C4 -54.5(9) . . . . ? C22 C2 C3 C4 65.5(10) . . . . ? C21 C2 C3 C4 -170.7(7) . . . . ? O1 C2 C3 Br1 65.6(8) . . . . ? C22 C2 C3 Br1 -174.4(6) . . . . ? C21 C2 C3 Br1 -50.6(9) . . . . ? C12 O2 C4 C4A 144.9(7) . . . . ? C12 O2 C4 C3 -94.2(8) . . . . ? C2 C3 C4 C4A 31.4(10) . . . . ? Br1 C3 C4 C4A -92.4(7) . . . . ? C2 C3 C4 O2 -86.0(8) . . . . ? Br1 C3 C4 O2 150.3(5) . . . . ? O2 C4 C4A C5 -69.4(9) . . . . ? C3 C4 C4A C5 172.4(7) . . . . ? O2 C4 C4A C10A 116.6(8) . . . . ? C3 C4 C4A C10A -1.6(11) . . . . ? C11 O5 C5 C4A -110.6(10) . . . . ? C11 O5 C5 C5A 75.6(11) . . . . ? C10A C4A C5 O5 -178.8(7) . . . . ? C4 C4A C5 O5 6.7(11) . . . . ? C10A C4A C5 C5A -4.9(12) . . . . ? C4 C4A C5 C5A -179.4(8) . . . . ? O5 C5 C5A C9A -178.9(7) . . . . ? C4A C5 C5A C9A 7.4(13) . . . . ? O5 C5 C5A C6 2.4(14) . . . . ? C4A C5 C5A C6 -171.3(8) . . . . ? C5 C5A C6 C7 -179.9(9) . . . . ? C9A C5A C6 C7 1.4(13) . . . . ? C5A C6 C7 C8 0.0(15) . . . . ? C6 C7 C8 C9 -1.5(16) . . . . ? C7 C8 C9 C9A 1.5(16) . . . . ? C5 C5A C9A N10 -5.3(13) . . . . ? C6 C5A C9A N10 173.5(8) . . . . ? C5 C5A C9A C9 179.8(8) . . . . ? C6 C5A C9A C9 -1.4(13) . . . . ? C8 C9 C9A N10 -175.2(8) . . . . ? C8 C9 C9A C5A 0.0(15) . . . . ? C5A C9A N10 C10A 0.6(12) . . . . ? C9 C9A N10 C10A 175.5(8) . . . . ? C9A N10 C10A O1 -178.4(7) . . . . ? C9A N10 C10A C4A 2.3(12) . . . . ? C2 O1 C10A N10 160.0(7) . . . . ? C2 O1 C10A C4A -20.7(11) . . . . ? C5 C4A C10A N10 -0.1(12) . . . . ? C4 C4A C10A N10 174.1(8) . . . . ? C5 C4A C10A O1 -179.4(7) . . . . ? C4 C4A C10A O1 -5.1(12) . . . . ? C4 O2 C12 O3 7.8(13) . . . . ? C4 O2 C12 C13 -174.7(6) . . . . ? C23 O4 C13 C15 54.9(10) . . . . ? C23 O4 C13 C14 173.6(8) . . . . ? C23 O4 C13 C12 -72.6(10) . . . . ? O3 C12 C13 O4 -118.8(10) . . . . ? O2 C12 C13 O4 63.7(9) . . . . ? O3 C12 C13 C15 112.0(10) . . . . ? O2 C12 C13 C15 -65.5(9) . . . . ? O3 C12 C13 C14 -8.4(12) . . . . ? O2 C12 C13 C14 174.1(7) . . . . ? O4 C13 C14 F1 -60.5(10) . . . . ? C15 C13 C14 F1 62.0(10) . . . . ? C12 C13 C14 F1 -176.1(8) . . . . ? O4 C13 C14 F2 179.6(7) . . . . ? C15 C13 C14 F2 -57.9(9) . . . . ? C12 C13 C14 F2 64.1(10) . . . . ? O4 C13 C14 F3 59.0(9) . . . . ? C15 C13 C14 F3 -178.4(7) . . . . ? C12 C13 C14 F3 -56.5(9) . . . . ? O4 C13 C15 C16 34.1(10) . . . . ? C14 C13 C15 C16 -80.3(9) . . . . ? C12 C13 C15 C16 160.5(7) . . . . ? O4 C13 C15 C20 -147.0(7) . . . . ? C14 C13 C15 C20 98.6(9) . . . . ? C12 C13 C15 C20 -20.6(11) . . . . ? C20 C15 C16 C17 0.2(13) . . . . ? C13 C15 C16 C17 179.1(8) . . . . ? C15 C16 C17 C18 -0.9(16) . . . . ? C16 C17 C18 C19 1.1(16) . . . . ? C17 C18 C19 C20 -0.7(16) . . . . ? C18 C19 C20 C15 0.0(15) . . . . ? C16 C15 C20 C19 0.3(12) . . . . ? C13 C15 C20 C19 -178.6(8) . . . . ? _diffrn_measured_fraction_theta_max 0.998 _diffrn_reflns_theta_full 27.56 _diffrn_measured_fraction_theta_full 0.998 _refine_diff_density_max 0.491 _refine_diff_density_min -0.380 _refine_diff_density_rms 0.080