Supplementary Material for Organic & Biomolecular Chemistry This journal is © The Royal Society of Chemistry 2004 Supplementary data data_global _journal_name_full Org.Biomol.Chem. _journal_coden_Cambridge 0177 _publ_contact_author_name 'Dr Craig M Williams' _publ_contact_author_address ; Chemistry University of Queensland Brisbane AUSTRALIA ; _publ_contact_author_email C.WILLIAMS3@MAILBOX.UQ.EDU.AU _publ_section_title ; Unprecedented photochemical induced cascading rearrangement of the 3-azabicyclo[3.3.1]nonane skeleton ; _publ_requested_category FO loop_ _publ_author_name 'Craig M. Williams' 'Paul V. Bernhardt' 'Douglas J. Brecknell' 'Ralf Heim' data_1950cw2 _database_code_depnum_ccdc_archive 'CCDC 224382' _audit_creation_date 2003-10-16T12:42:42-00:00 _audit_creation_method 'WinGX routine CIF_UPDATE' _audit_conform_dict_name cif_core.dic _audit_conform_dict_version 2.1 _audit_conform_dict_location ftp://ftp.iucr.org/cifdics/cif_core.dic #----------------------------------------------------------------------------# # CHEMICAL INFORMATION # #----------------------------------------------------------------------------# _chemical_name_systematic ; ? ; _chemical_formula_moiety 'C24 H32 Br1 N1 O5' _chemical_formula_structural 'C24 H32 BR N O5' _chemical_formula_sum 'C24 H32 Br N O5' _chemical_formula_weight 494.42 _chemical_compound_source 'synthesis as described' #----------------------------------------------------------------------------# # UNIT CELL INFORMATION # #----------------------------------------------------------------------------# _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M 'C 2/c' _symmetry_space_group_name_Hall '-C 2yc' _symmetry_Int_Tables_number 15 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y, -z+1/2' 'x+1/2, y+1/2, z' '-x+1/2, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y, z-1/2' '-x+1/2, -y+1/2, -z' 'x+1/2, -y+1/2, z-1/2' _cell_length_a 25.75(1) _cell_length_b 11.464(2) _cell_length_c 20.370(7) _cell_angle_alpha 90 _cell_angle_beta 125.61(2) _cell_angle_gamma 90 _cell_volume 4889(3) _cell_formula_units_Z 8 _cell_measurement_temperature 296(2) _cell_measurement_reflns_used 16 _cell_measurement_theta_min 9.072 _cell_measurement_theta_max 12.652 _cell_measurement_wavelength 0.71073 #----------------------------------------------------------------------------# # CRYSTAL INFORMATION # #----------------------------------------------------------------------------# _exptl_crystal_description prism _exptl_crystal_colour yellow _exptl_crystal_size_max 0.5 _exptl_crystal_size_mid 0.5 _exptl_crystal_size_min 0.3 _exptl_crystal_density_diffrn 1.343 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 2064 _exptl_special_details ; ? ; #----------------------------------------------------------------------------# # ABSORPTION CORRECTION # #----------------------------------------------------------------------------# _exptl_absorpt_coefficient_mu 1.715 _exptl_absorpt_factor_muR 0.514 _exptl_absorpt_correction_type psi-scan _exptl_absorpt_process_details ; North A.C.T., Phillips D.C. & Mathews F.S. (1968) Acta. Cryst. A24, 351 Number of psi-scan sets used was 5 Theta correction was applied. Averaged transmission function was used. No Fourier smoothing was applied. ; _exptl_absorpt_correction_T_min 0.481 _exptl_absorpt_correction_T_max 0.6272 _exptl_absorpt_correction_T_ave 0.5276 #----------------------------------------------------------------------------# # DATA COLLECTION # #----------------------------------------------------------------------------# _diffrn_source 'Enraf Nonius FR590' _diffrn_ambient_temperature 296(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_monochromator graphite _diffrn_radiation_probe x-ray _diffrn_detector 'scintillation LiI' _diffrn_detector_dtime 1.195 _diffrn_orient_matrix_type ; x-axis points to radiation source the matrix is specified in reciprocal space ; _diffrn_orient_matrix_ub_11 -0.13371E-1 _diffrn_orient_matrix_ub_12 -0.61799E-1 _diffrn_orient_matrix_ub_13 -0.41609E-1 _diffrn_orient_matrix_ub_21 0.38718E-1 _diffrn_orient_matrix_ub_22 -0.46733E-1 _diffrn_orient_matrix_ub_23 0.40068E-1 _diffrn_orient_matrix_ub_31 -0.24578E-1 _diffrn_orient_matrix_ub_32 -0.04003 _diffrn_orient_matrix_ub_33 0.17505E-1 _diffrn_measurement_device '\k-geometry diffractometer' _diffrn_measurement_device_type 'Enraf Nonius TurboCAD4' _diffrn_measurement_method 'non-profiled omega scans' _diffrn_standards_number 3 _diffrn_standards_interval_time 120 _diffrn_standards_decay_% 19 _diffrn_standards_decay_corr_max 1.294 _diffrn_standards_decay_corr_min 1 loop_ _diffrn_standard_refln_index_h _diffrn_standard_refln_index_k _diffrn_standard_refln_index_l 8 -4 3 1 3 8 -7 -5 5 _diffrn_reflns_number 4395 _diffrn_reflns_av_R_equivalents 0.0461 _diffrn_reflns_av_unetI/netI 0.0746 _diffrn_reflns_limit_h_min 0 _diffrn_reflns_limit_h_max 30 _diffrn_reflns_limit_k_min 0 _diffrn_reflns_limit_k_max 13 _diffrn_reflns_limit_l_min -24 _diffrn_reflns_limit_l_max 19 _diffrn_reflns_theta_min 1.95 _diffrn_reflns_theta_max 24.97 _diffrn_reflns_theta_full 24.97 _diffrn_measured_fraction_theta_full 1 _diffrn_measured_fraction_theta_max 1 _reflns_number_total 4295 _reflns_number_gt 1781 _reflns_threshold_expression >2sigma(I) #----------------------------------------------------------------------------# # COMPUTER PROGRAMS USED # #----------------------------------------------------------------------------# _computing_data_collection 'CAD4 Express (Enraf Nonius, 1994)' _computing_cell_refinement 'CAD4 Express (Enraf Nonius, 1994)' _computing_data_reduction 'XCAD4 (Harms & Wocadlo, 1995)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Ortep-3 for Windows (Farrugia, 1997)' _computing_publication_material 'WinGX publication routines (Farrugia, 1999)' #----------------------------------------------------------------------------# # REFINEMENT INFORMATION # #----------------------------------------------------------------------------# _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^)+(0.0733P)^2^+3.6966P] 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 constr _refine_ls_extinction_method none _refine_ls_number_reflns 4295 _refine_ls_number_parameters 286 _refine_ls_number_restraints 8 _refine_ls_R_factor_all 0.1682 _refine_ls_R_factor_gt 0.0529 _refine_ls_wR_factor_ref 0.1662 _refine_ls_wR_factor_gt 0.1241 _refine_ls_goodness_of_fit_ref 0.998 _refine_ls_restrained_S_all 0.997 _refine_ls_shift/su_max 0 _refine_ls_shift/su_mean 0 _refine_diff_density_max 0.28 _refine_diff_density_min -0.283 _refine_diff_density_rms 0.05 #----------------------------------------------------------------------------# # ATOMIC TYPES, COORDINATES AND THERMAL PARAMETERS # #----------------------------------------------------------------------------# 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 0 '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 0.006 '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' loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group C1 C 0.2259(2) 0.0621(5) 0.1754(3) 0.0741(15) Uani 1 1 d . . . C2 C 0.1931(3) 0.1812(6) 0.1427(4) 0.0958(19) Uani 1 1 d . . . H2A H 0.1479 0.1722 0.1187 0.115 Uiso 1 1 calc R . . H2B H 0.2105 0.2349 0.1877 0.115 Uiso 1 1 calc R . . C3 C 0.2005(3) 0.2344(6) 0.0807(4) 0.108(2) Uani 1 1 d . . . H3A H 0.1815 0.3115 0.0662 0.13 Uiso 1 1 calc R . . H3B H 0.1785 0.1866 0.0324 0.13 Uiso 1 1 calc R . . C4 C 0.2707(3) 0.2427(6) 0.1150(4) 0.0997(19) Uani 1 1 d . . . H4A H 0.2926 0.2906 0.1633 0.12 Uiso 1 1 calc R . . H4B H 0.2754 0.2792 0.0758 0.12 Uiso 1 1 calc R . . C5 C 0.2999(2) 0.1216(6) 0.1352(3) 0.0791(16) Uani 1 1 d . A . H5 H 0.2766 0.0757 0.0853 0.095 Uiso 1 1 calc R . . C6 C 0.2948(2) 0.0571(5) 0.1971(3) 0.0682(15) Uani 1 1 d . . . C7 C 0.3344(3) 0.1035(5) 0.2857(3) 0.0756(16) Uani 1 1 d . . . H7 H 0.3519 0.1809 0.2887 0.091 Uiso 1 1 calc R . . C8 C 0.2373(3) 0.0353(5) 0.2550(4) 0.0847(18) Uani 1 1 d . . . H8A H 0.2009 0.0568 0.2552 0.102 Uiso 1 1 calc R . . H8B H 0.2472 -0.0465 0.2692 0.102 Uiso 1 1 calc R . . C9 C 0.3180(3) 0.1110(7) 0.3924(4) 0.114(2) Uani 1 1 d . . . H9A H 0.2837 0.1151 0.3984 0.171 Uiso 1 1 calc R . . H9B H 0.3452 0.1777 0.4174 0.171 Uiso 1 1 calc R . . H9C H 0.3423 0.0411 0.4176 0.171 Uiso 1 1 calc R . . C10 C 0.3695(3) 0.1312(7) 0.1635(4) 0.104(2) Uani 1 1 d . . . C11A C 0.4418(6) 0.1432(14) 0.1346(8) 0.106(5) Uiso 0.493(11) 1 d PD A 1 H11A H 0.4464 0.2235 0.1238 0.127 Uiso 0.493(11) 1 calc PR A 1 H11B H 0.4733 0.1275 0.1915 0.127 Uiso 0.493(11) 1 calc PR A 1 C12A C 0.4504(8) 0.0624(17) 0.0845(10) 0.134(6) Uiso 0.493(11) 1 d PD A 1 H12A H 0.4936 0.0673 0.1007 0.201 Uiso 0.493(11) 1 calc PR A 1 H12B H 0.4216 0.0838 0.0286 0.201 Uiso 0.493(11) 1 calc PR A 1 H12C H 0.4416 -0.016 0.0917 0.201 Uiso 0.493(11) 1 calc PR A 1 C11B C 0.4433(6) 0.0484(13) 0.1299(9) 0.103(5) Uiso 0.507(11) 1 d PD A 2 H11C H 0.4737 0.0599 0.1876 0.124 Uiso 0.507(11) 1 calc PR A 2 H11D H 0.451 -0.0279 0.1166 0.124 Uiso 0.507(11) 1 calc PR A 2 C12B C 0.4526(6) 0.1398(12) 0.0859(8) 0.103(5) Uiso 0.507(11) 1 d PD A 2 H12D H 0.497 0.1438 0.1069 0.155 Uiso 0.507(11) 1 calc PR A 2 H12E H 0.4391 0.2139 0.093 0.155 Uiso 0.507(11) 1 calc PR A 2 H12F H 0.4279 0.1208 0.0295 0.155 Uiso 0.507(11) 1 calc PR A 2 C13 C 0.3211(2) -0.0645(5) 0.2106(3) 0.0681(15) Uani 1 1 d . . . H13 H 0.304 -0.1222 0.1713 0.082 Uiso 1 1 calc R . . C14 C 0.3717(2) -0.0784(5) 0.2861(3) 0.0698(15) Uani 1 1 d . . . C15 C 0.4149(2) -0.1770(6) 0.3308(3) 0.0677(15) Uani 1 1 d . . . C16 C 0.4109(2) -0.2821(6) 0.2942(4) 0.0735(16) Uani 1 1 d . . . C17 C 0.4489(3) -0.3770(7) 0.3401(4) 0.0868(18) Uani 1 1 d . . . C18 C 0.4931(3) -0.3635(7) 0.4222(5) 0.095(2) Uani 1 1 d . . . H18 H 0.5194 -0.4255 0.4533 0.114 Uiso 1 1 calc R . . C19 C 0.4981(3) -0.2601(7) 0.4577(4) 0.092(2) Uani 1 1 d . . . H19 H 0.5283 -0.252 0.5131 0.111 Uiso 1 1 calc R . . C20 C 0.4599(2) -0.1668(6) 0.4141(3) 0.0789(16) Uani 1 1 d . . . H20 H 0.4639 -0.0971 0.4401 0.095 Uiso 1 1 calc R . . C21 C 0.3862(4) -0.3278(7) 0.1621(5) 0.126(3) Uani 1 1 d D . . H21A H 0.427 -0.3694 0.1951 0.151 Uiso 0.39(4) 1 d PR B 1 H21B H 0.4325 -0.3406 0.1945 0.151 Uiso 0.303(19) 1 d PR B 2 H21C H 0.4098 -0.4013 0.175 0.151 Uiso 0.303(19) 1 d PR B 3 C22A C 0.4011(14) -0.2159(13) 0.1390(18) 0.098(9) Uiso 0.39(4) 1 d PD B 1 H22A H 0.4341 -0.1754 0.1868 0.147 Uiso 0.39(4) 1 calc PR B 1 H22B H 0.3634 -0.1683 0.1096 0.147 Uiso 0.39(4) 1 calc PR B 1 H22C H 0.4155 -0.232 0.1057 0.147 Uiso 0.39(4) 1 calc PR B 1 C23A C 0.339(2) -0.415(4) 0.102(3) 0.16(2) Uiso 0.39(4) 1 d PD B 1 H23A H 0.3387 -0.4821 0.1292 0.24 Uiso 0.39(4) 1 calc PR B 1 H23B H 0.3513 -0.4376 0.0669 0.24 Uiso 0.39(4) 1 calc PR B 1 H23C H 0.2974 -0.3804 0.0698 0.24 Uiso 0.39(4) 1 calc PR B 1 C22B C 0.3679(15) -0.240(2) 0.0980(16) 0.093(9) Uiso 0.303(19) 1 d PD B 2 H22D H 0.3898 -0.1684 0.1226 0.14 Uiso 0.303(19) 1 calc PR B 2 H22E H 0.3226 -0.2275 0.0664 0.14 Uiso 0.303(19) 1 calc PR B 2 H22F H 0.3794 -0.2689 0.0638 0.14 Uiso 0.303(19) 1 calc PR B 2 C23B C 0.348(2) -0.434(3) 0.116(3) 0.14(2) Uiso 0.303(19) 1 d PD B 2 H23D H 0.3621 -0.4988 0.1525 0.213 Uiso 0.303(19) 1 calc PR B 2 H23E H 0.3545 -0.4514 0.0752 0.213 Uiso 0.303(19) 1 calc PR B 2 H23F H 0.3037 -0.4194 0.0914 0.213 Uiso 0.303(19) 1 calc PR B 2 C22C C 0.424(2) -0.223(3) 0.169(3) 0.21(3) Uiso 0.303(19) 1 d PD B 3 H22G H 0.4646 -0.2239 0.2201 0.311 Uiso 0.303(19) 1 calc PR B 3 H22H H 0.4009 -0.1536 0.1648 0.311 Uiso 0.303(19) 1 calc PR B 3 H22I H 0.429 -0.2238 0.1261 0.311 Uiso 0.303(19) 1 calc PR B 3 C23C C 0.3266(10) -0.317(5) 0.0783(9) 0.169(15) Uiso 0.303(19) 1 d PD B 3 H23G H 0.2989 -0.3816 0.0673 0.254 Uiso 0.303(19) 1 calc PR B 3 H23H H 0.3373 -0.3173 0.0404 0.254 Uiso 0.303(19) 1 calc PR B 3 H23I H 0.3054 -0.2454 0.0735 0.254 Uiso 0.303(19) 1 calc PR B 3 C24 C 0.4732(5) -0.5777(7) 0.3438(6) 0.171(4) Uani 1 1 d . . . H24A H 0.4603 -0.6428 0.3078 0.256 Uiso 1 1 calc R . . H24B H 0.4654 -0.5951 0.3836 0.256 Uiso 1 1 calc R . . H24C H 0.5179 -0.563 0.3703 0.256 Uiso 1 1 calc R . . N1 N 0.2922(2) 0.1094(4) 0.3082(3) 0.0834(14) Uani 1 1 d . . . O1 O 0.4100(2) 0.1728(5) 0.2227(3) 0.140(2) Uani 1 1 d . A . O2A O 0.3754(4) 0.1222(10) 0.1118(5) 0.076(3) Uiso 0.493(11) 1 d P A 1 O2B O 0.3763(4) 0.0537(10) 0.1073(5) 0.079(3) Uiso 0.507(11) 1 d P A 2 O3 O 0.38610(16) 0.0195(4) 0.3331(2) 0.0813(11) Uani 1 1 d . . . O4 O 0.36549(17) -0.2968(3) 0.2137(2) 0.0839(11) Uani 1 1 d . B . O5 O 0.4381(2) -0.4789(5) 0.2999(3) 0.1201(16) Uani 1 1 d . . . Br1 Br 0.17022(3) -0.05662(7) 0.09487(4) 0.1068(4) 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 C1 0.051(3) 0.083(4) 0.077(4) -0.009(3) 0.031(3) 0.006(3) C2 0.073(4) 0.102(5) 0.099(5) -0.004(4) 0.042(3) 0.022(4) C3 0.091(5) 0.111(5) 0.094(5) 0.029(4) 0.038(4) 0.046(4) C4 0.097(5) 0.093(5) 0.093(4) 0.024(4) 0.046(4) 0.010(4) C5 0.056(3) 0.096(5) 0.071(4) 0.010(3) 0.029(3) 0.008(3) C6 0.049(3) 0.089(4) 0.062(3) -0.001(3) 0.030(3) 0.003(3) C7 0.071(4) 0.074(4) 0.076(4) 0.007(3) 0.039(3) 0.004(3) C8 0.068(4) 0.099(5) 0.091(4) -0.006(4) 0.048(3) 0.009(4) C9 0.128(6) 0.135(6) 0.080(5) -0.008(4) 0.062(4) 0.012(5) C10 0.071(4) 0.151(7) 0.067(4) 0.021(5) 0.028(4) -0.013(5) C13 0.052(3) 0.082(4) 0.068(4) -0.003(3) 0.033(3) 0.008(3) C14 0.052(3) 0.086(5) 0.074(4) -0.003(4) 0.038(3) 0.000(3) C15 0.049(3) 0.086(4) 0.073(4) 0.016(4) 0.038(3) 0.009(3) C16 0.058(3) 0.098(5) 0.069(4) 0.016(4) 0.039(3) 0.012(4) C17 0.066(4) 0.098(6) 0.092(5) 0.020(5) 0.044(4) 0.021(4) C18 0.072(4) 0.108(6) 0.104(6) 0.034(5) 0.051(5) 0.023(4) C19 0.056(3) 0.123(6) 0.078(4) 0.028(5) 0.028(3) 0.006(4) C20 0.056(3) 0.102(5) 0.067(4) 0.009(4) 0.029(3) 0.002(4) C21 0.124(6) 0.149(7) 0.116(6) -0.001(6) 0.076(5) 0.019(6) C24 0.173(9) 0.099(7) 0.200(10) 0.031(6) 0.086(8) 0.054(6) N1 0.072(3) 0.103(4) 0.073(3) -0.012(3) 0.041(3) 0.003(3) O1 0.069(3) 0.206(6) 0.122(4) -0.020(4) 0.042(3) -0.035(4) O3 0.058(2) 0.093(3) 0.068(2) 0.000(2) 0.0228(19) 0.004(2) O4 0.077(2) 0.105(3) 0.077(3) 0.007(2) 0.049(2) 0.025(2) O5 0.127(4) 0.104(4) 0.124(4) 0.020(4) 0.070(3) 0.040(3) Br1 0.0597(4) 0.1283(6) 0.1113(6) -0.0345(4) 0.0377(4) -0.0119(4) #----------------------------------------------------------------------------# # MOLECULAR GEOMETRY # #----------------------------------------------------------------------------# _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 C1 C8 1.503(8) . ? C1 C2 1.538(8) . ? C1 C6 1.559(7) . ? C1 Br1 1.965(5) . ? C2 C3 1.510(8) . ? C3 C4 1.515(8) . ? C4 C5 1.518(8) . ? C5 C6 1.531(7) . ? C5 C10 1.535(8) . ? C6 C13 1.503(7) . ? C6 C7 1.561(7) . ? C7 N1 1.409(7) . ? C7 O3 1.461(6) . ? C8 N1 1.452(7) . ? C9 N1 1.433(6) . ? C10 O1 1.143(7) . ? C10 O2A 1.152(9) . ? C10 O2B 1.539(13) . ? C11A C12A 1.489(7) . ? C11A O2A 1.507(14) . ? C11B C12B 1.487(7) . ? C11B O2B 1.505(14) . ? C13 C14 1.324(7) . ? C14 O3 1.379(6) . ? C14 C15 1.471(7) . ? C15 C16 1.387(8) . ? C15 C20 1.396(7) . ? C16 O4 1.361(6) . ? C16 C17 1.396(8) . ? C17 O5 1.358(8) . ? C17 C18 1.379(8) . ? C18 C19 1.355(9) . ? C19 C20 1.371(8) . ? C21 O4 1.473(7) . ? C21 C22B 1.488(7) . ? C21 C22A 1.492(7) . ? C21 C23C 1.494(8) . ? C21 C22C 1.495(8) . ? C21 C23A 1.497(7) . ? C21 C23B 1.498(8) . ? C24 O5 1.400(8) . ? 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 C8 C1 C2 111.2(5) . . ? C8 C1 C6 102.3(4) . . ? C2 C1 C6 113.7(5) . . ? C8 C1 Br1 110.4(4) . . ? C2 C1 Br1 107.6(4) . . ? C6 C1 Br1 111.6(4) . . ? C3 C2 C1 114.6(5) . . ? C2 C3 C4 109.7(5) . . ? C3 C4 C5 109.7(5) . . ? C4 C5 C6 113.5(5) . . ? C4 C5 C10 108.8(5) . . ? C6 C5 C10 111.5(4) . . ? C13 C6 C5 110.7(4) . . ? C13 C6 C1 113.7(4) . . ? C5 C6 C1 112.1(4) . . ? C13 C6 C7 100.5(4) . . ? C5 C6 C7 118.4(5) . . ? C1 C6 C7 100.7(4) . . ? N1 C7 O3 113.3(4) . . ? N1 C7 C6 106.5(4) . . ? O3 C7 C6 105.7(4) . . ? N1 C8 C1 100.3(4) . . ? O1 C10 O2A 118.5(8) . . ? O1 C10 C5 125.1(7) . . ? O2A C10 C5 113.4(7) . . ? O1 C10 O2B 126.7(7) . . ? O2A C10 O2B 30.1(6) . . ? C5 C10 O2B 107.1(6) . . ? C12A C11A O2A 106.6(12) . . ? C12B C11B O2B 110.2(10) . . ? C14 C13 C6 111.1(5) . . ? C13 C14 O3 113.1(5) . . ? C13 C14 C15 133.6(6) . . ? O3 C14 C15 113.3(5) . . ? C16 C15 C20 118.4(5) . . ? C16 C15 C14 122.8(5) . . ? C20 C15 C14 118.7(6) . . ? O4 C16 C15 119.8(5) . . ? O4 C16 C17 119.1(6) . . ? C15 C16 C17 120.9(6) . . ? O5 C17 C18 124.2(7) . . ? O5 C17 C16 116.7(6) . . ? C18 C17 C16 119.1(7) . . ? C19 C18 C17 120.0(7) . . ? C18 C19 C20 121.9(6) . . ? C19 C20 C15 119.7(6) . . ? O4 C21 C22B 113.7(11) . . ? O4 C21 C22A 106.5(10) . . ? C22B C21 C22A 32.0(12) . . ? O4 C21 C23C 103.7(14) . . ? C22B C21 C23C 50(2) . . ? C22A C21 C23C 81(2) . . ? O4 C21 C22C 103(2) . . ? C22B C21 C22C 53(3) . . ? C22A C21 C22C 21(3) . . ? C23C C21 C22C 103(2) . . ? O4 C21 C23A 107(2) . . ? C22B C21 C23A 92(3) . . ? C22A C21 C23A 123(2) . . ? C23C C21 C23A 46.7(18) . . ? C22C C21 C23A 141(3) . . ? O4 C21 C23B 105(2) . . ? C22B C21 C23B 104(3) . . ? C22A C21 C23B 134(3) . . ? C23C C21 C23B 59(4) . . ? C22C C21 C23B 150(3) . . ? C23A C21 C23B 13(4) . . ? C7 N1 C9 118.8(5) . . ? C7 N1 C8 109.3(4) . . ? C9 N1 C8 118.2(5) . . ? C10 O2A C11A 115.7(9) . . ? C11B O2B C10 113.8(9) . . ? C14 O3 C7 107.8(4) . . ? C16 O4 C21 118.4(5) . . ? C17 O5 C24 118.8(6) . . ? 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 C8 C1 C2 C3 159.5(5) . . . . ? C6 C1 C2 C3 44.7(7) . . . . ? Br1 C1 C2 C3 -79.5(5) . . . . ? C1 C2 C3 C4 -55.0(7) . . . . ? C2 C3 C4 C5 61.2(7) . . . . ? C3 C4 C5 C6 -59.6(7) . . . . ? C3 C4 C5 C10 175.6(6) . . . . ? C4 C5 C6 C13 176.7(4) . . . . ? C10 C5 C6 C13 -60.0(7) . . . . ? C4 C5 C6 C1 48.5(6) . . . . ? C10 C5 C6 C1 171.8(5) . . . . ? C4 C5 C6 C7 -68.1(6) . . . . ? C10 C5 C6 C7 55.2(7) . . . . ? C8 C1 C6 C13 73.3(5) . . . . ? C2 C1 C6 C13 -166.7(5) . . . . ? Br1 C1 C6 C13 -44.7(5) . . . . ? C8 C1 C6 C5 -160.1(5) . . . . ? C2 C1 C6 C5 -40.1(6) . . . . ? Br1 C1 C6 C5 81.9(5) . . . . ? C8 C1 C6 C7 -33.3(5) . . . . ? C2 C1 C6 C7 86.7(5) . . . . ? Br1 C1 C6 C7 -151.3(4) . . . . ? C13 C6 C7 N1 -107.5(5) . . . . ? C5 C6 C7 N1 131.9(5) . . . . ? C1 C6 C7 N1 9.3(6) . . . . ? C13 C6 C7 O3 13.3(5) . . . . ? C5 C6 C7 O3 -107.4(5) . . . . ? C1 C6 C7 O3 130.1(4) . . . . ? C2 C1 C8 N1 -76.7(5) . . . . ? C6 C1 C8 N1 45.0(5) . . . . ? Br1 C1 C8 N1 163.9(3) . . . . ? C4 C5 C10 O1 69.0(9) . . . . ? C6 C5 C10 O1 -56.9(10) . . . . ? C4 C5 C10 O2A -90.9(10) . . . . ? C6 C5 C10 O2A 143.1(9) . . . . ? C4 C5 C10 O2B -122.4(6) . . . . ? C6 C5 C10 O2B 111.7(7) . . . . ? C5 C6 C13 C14 116.4(5) . . . . ? C1 C6 C13 C14 -116.3(5) . . . . ? C7 C6 C13 C14 -9.6(5) . . . . ? C6 C13 C14 O3 1.9(6) . . . . ? C6 C13 C14 C15 -179.8(5) . . . . ? C13 C14 C15 C16 4.8(9) . . . . ? O3 C14 C15 C16 -176.9(4) . . . . ? C13 C14 C15 C20 -171.9(6) . . . . ? O3 C14 C15 C20 6.3(6) . . . . ? C20 C15 C16 O4 176.8(4) . . . . ? C14 C15 C16 O4 0.1(7) . . . . ? C20 C15 C16 C17 2.7(8) . . . . ? C14 C15 C16 C17 -174.1(5) . . . . ? O4 C16 C17 O5 0.7(8) . . . . ? C15 C16 C17 O5 174.9(5) . . . . ? O4 C16 C17 C18 -177.3(5) . . . . ? C15 C16 C17 C18 -3.0(8) . . . . ? O5 C17 C18 C19 -176.3(6) . . . . ? C16 C17 C18 C19 1.5(9) . . . . ? C17 C18 C19 C20 0.5(10) . . . . ? C18 C19 C20 C15 -0.9(9) . . . . ? C16 C15 C20 C19 -0.7(7) . . . . ? C14 C15 C20 C19 176.2(5) . . . . ? O3 C7 N1 C9 43.6(7) . . . . ? C6 C7 N1 C9 159.3(5) . . . . ? O3 C7 N1 C8 -96.2(5) . . . . ? C6 C7 N1 C8 19.6(6) . . . . ? C1 C8 N1 C7 -41.1(6) . . . . ? C1 C8 N1 C9 178.8(5) . . . . ? O1 C10 O2A C11A 12.6(16) . . . . ? C5 C10 O2A C11A 173.9(9) . . . . ? O2B C10 O2A C11A -102.2(15) . . . . ? C12A C11A O2A C10 145.4(15) . . . . ? C12B C11B O2B C10 -92.1(14) . . . . ? O1 C10 O2B C11B -8.5(13) . . . . ? O2A C10 O2B C11B 75.9(12) . . . . ? C5 C10 O2B C11B -176.8(7) . . . . ? C13 C14 O3 C7 7.4(6) . . . . ? C15 C14 O3 C7 -171.2(4) . . . . ? N1 C7 O3 C14 103.2(5) . . . . ? C6 C7 O3 C14 -13.1(5) . . . . ? C15 C16 O4 C21 122.5(6) . . . . ? C17 C16 O4 C21 -63.2(7) . . . . ? C22B C21 O4 C16 -119.3(17) . . . . ? C22A C21 O4 C16 -85.9(14) . . . . ? C23C C21 O4 C16 -171(2) . . . . ? C22C C21 O4 C16 -64(2) . . . . ? C23A C21 O4 C16 141(2) . . . . ? C23B C21 O4 C16 128(3) . . . . ? C18 C17 O5 C24 0.5(10) . . . . ? C16 C17 O5 C24 -177.3(6) . . . . ? #===END # compound 10 # CIF produced by WinGX routine CIF_UPDATE # Created on 2003-10-16 at 13:33:29 # Using CIFtbx version 2.6.2 16 Jun 1998 # Dictionary name : cif_core.dic # Dictionary vers : 2.1 # Request file : c:\wingx\files\archive.dat # CIF files read : 2020cw12 dreduc struct psi_scan data_2020cw12 _database_code_depnum_ccdc_archive 'CCDC 224383' _audit_creation_date 2003-10-16T13:33:29-00:00 _audit_creation_method 'WinGX routine CIF_UPDATE' _audit_conform_dict_name cif_core.dic _audit_conform_dict_version 2.1 _audit_conform_dict_location ftp://ftp.iucr.org/cifdics/cif_core.dic #----------------------------------------------------------------------------# # CHEMICAL INFORMATION # #----------------------------------------------------------------------------# _chemical_name_systematic ; ? ; _chemical_formula_moiety 'C32 H39 N1 O8' _chemical_formula_structural 'C32 H39 N O8' _chemical_formula_sum 'C32 H39 N O8' _chemical_formula_weight 565.64 _chemical_compound_source 'synthesis as described' #----------------------------------------------------------------------------# # UNIT CELL INFORMATION # #----------------------------------------------------------------------------# _symmetry_cell_setting triclinic _symmetry_space_group_name_H-M 'P -1' _symmetry_space_group_name_Hall '-P 1' _symmetry_Int_Tables_number 2 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 7.2889(8) _cell_length_b 12.260(1) _cell_length_c 16.917(4) _cell_angle_alpha 99.24(1) _cell_angle_beta 97.78(2) _cell_angle_gamma 90.40(1) _cell_volume 1477.7(4) _cell_formula_units_Z 2 _cell_measurement_temperature 150(2) _cell_measurement_reflns_used 25 _cell_measurement_theta_min 9.222 _cell_measurement_theta_max 14.197 _cell_measurement_wavelength 0.71073 #----------------------------------------------------------------------------# # CRYSTAL INFORMATION # #----------------------------------------------------------------------------# _exptl_crystal_description prism _exptl_crystal_colour colourless _exptl_crystal_size_max 0.27 _exptl_crystal_size_mid 0.13 _exptl_crystal_size_min 0.13 _exptl_crystal_density_diffrn 1.271 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 604 _exptl_special_details ; ? ; #----------------------------------------------------------------------------# # ABSORPTION CORRECTION # #----------------------------------------------------------------------------# _exptl_absorpt_coefficient_mu 0.091 _exptl_absorpt_factor_muR 0.012 _exptl_absorpt_correction_type psi-scan _exptl_absorpt_process_details ; North A.C.T., Phillips D.C. & Mathews F.S. (1968) Acta. Cryst. A24, 351 Number of psi-scan sets used was 1 Theta correction was applied. Averaged transmission function was used. No Fourier smoothing was applied. ; _exptl_absorpt_correction_T_min 0.9759 _exptl_absorpt_correction_T_max 0.9883 _exptl_absorpt_correction_T_ave 0.9152 #----------------------------------------------------------------------------# # DATA COLLECTION # #----------------------------------------------------------------------------# _diffrn_source 'Enraf Nonius FR590' _diffrn_ambient_temperature 150(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_monochromator graphite _diffrn_radiation_probe x-ray _diffrn_detector 'scintillation LiI' _diffrn_detector_dtime 1.195 _diffrn_orient_matrix_type ; x-axis points to radiation source the matrix is specified in reciprocal space ; _diffrn_orient_matrix_ub_11 -0.16235E-1 _diffrn_orient_matrix_ub_12 0.8496E-2 _diffrn_orient_matrix_ub_13 -0.58302E-1 _diffrn_orient_matrix_ub_21 -0.01433 _diffrn_orient_matrix_ub_22 0.81349E-1 _diffrn_orient_matrix_ub_23 0.01558 _diffrn_orient_matrix_ub_31 0.136818 _diffrn_orient_matrix_ub_32 0.11984E-1 _diffrn_orient_matrix_ub_33 0.3345E-2 _diffrn_measurement_device '\k-geometry diffractometer' _diffrn_measurement_device_type 'Enraf Nonius TurboCAD4' _diffrn_measurement_method 'non-profiled omega/2theta scans' _diffrn_standards_number 3 _diffrn_standards_interval_time 120 _diffrn_standards_decay_% 6 _diffrn_standards_decay_corr_max 1.155 _diffrn_standards_decay_corr_min 0.947 loop_ _diffrn_standard_refln_index_h _diffrn_standard_refln_index_k _diffrn_standard_refln_index_l -1 8 -3 4 2 1 4 3 -3 _diffrn_reflns_number 5646 _diffrn_reflns_av_R_equivalents 0.0783 _diffrn_reflns_av_unetI/netI 0.2483 _diffrn_reflns_limit_h_min 0 _diffrn_reflns_limit_h_max 8 _diffrn_reflns_limit_k_min -14 _diffrn_reflns_limit_k_max 14 _diffrn_reflns_limit_l_min -20 _diffrn_reflns_limit_l_max 19 _diffrn_reflns_theta_min 1.68 _diffrn_reflns_theta_max 25.01 _diffrn_reflns_theta_full 25.01 _diffrn_measured_fraction_theta_full 0.995 _diffrn_measured_fraction_theta_max 0.995 _reflns_number_total 5198 _reflns_number_gt 1814 _reflns_threshold_expression >2sigma(I) #----------------------------------------------------------------------------# # COMPUTER PROGRAMS USED # #----------------------------------------------------------------------------# _computing_data_collection 'CAD4 Express (Enraf Nonius, 1994)' _computing_cell_refinement 'CAD4 Express (Enraf Nonius, 1994)' _computing_data_reduction 'XCAD4 (Harms & Wocadlo, 1995)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Ortep-3 for Windows (Farrugia, 1997)' _computing_publication_material 'WinGX publication routines (Farrugia, 1999)' #----------------------------------------------------------------------------# # REFINEMENT INFORMATION # #----------------------------------------------------------------------------# _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^)+(0.1369P)^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 constr _refine_ls_extinction_method none _refine_ls_number_reflns 5198 _refine_ls_number_parameters 370 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.2611 _refine_ls_R_factor_gt 0.0776 _refine_ls_wR_factor_ref 0.2736 _refine_ls_wR_factor_gt 0.1871 _refine_ls_goodness_of_fit_ref 0.961 _refine_ls_restrained_S_all 0.961 _refine_ls_shift/su_max 0 _refine_ls_shift/su_mean 0 _refine_diff_density_max 0.37 _refine_diff_density_min -0.603 _refine_diff_density_rms 0.104 #----------------------------------------------------------------------------# # ATOMIC TYPES, COORDINATES AND THERMAL PARAMETERS # #----------------------------------------------------------------------------# 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 0 '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 0.006 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group C1 C 0.3644(9) 0.2591(5) 0.3697(4) 0.0178(15) Uani 1 1 d . . . C2 C 0.2118(9) 0.2805(5) 0.4262(4) 0.0224(16) Uani 1 1 d . . . H2A H 0.0927 0.248 0.3962 0.027 Uiso 1 1 calc R . . H2B H 0.244 0.2412 0.4728 0.027 Uiso 1 1 calc R . . C3 C 0.1849(11) 0.3995(6) 0.4577(4) 0.0329(19) Uani 1 1 d . . . H3A H 0.2985 0.4311 0.4931 0.039 Uiso 1 1 calc R . . H3B H 0.0814 0.4059 0.4904 0.039 Uiso 1 1 calc R . . C4 C 0.1425(11) 0.4639(6) 0.3877(4) 0.0323(19) Uani 1 1 d . . . H4A H 0.0294 0.4319 0.3521 0.039 Uiso 1 1 calc R . . H4B H 0.1192 0.5418 0.409 0.039 Uiso 1 1 calc R . . C5 C 0.3033(10) 0.4591(5) 0.3396(4) 0.0239(17) Uani 1 1 d . . . H5 H 0.4138 0.495 0.3763 0.029 Uiso 1 1 calc R . . C6 C 0.3535(9) 0.3409(5) 0.3063(4) 0.0201(16) Uani 1 1 d . . . C7 C 0.2154(9) 0.2789(5) 0.2339(4) 0.0202(16) Uani 1 1 d . . . H7 H 0.1024 0.3234 0.2244 0.024 Uiso 1 1 calc R . . C8 C 0.3215(9) 0.1467(5) 0.3140(4) 0.0195(15) Uani 1 1 d . . . H8A H 0.4284 0.121 0.2863 0.023 Uiso 1 1 calc R . . H8B H 0.2831 0.0893 0.3439 0.023 Uiso 1 1 calc R . . C9 C 0.5505(10) 0.2657(5) 0.4231(4) 0.0226(16) Uani 1 1 d . . . C10 C 0.7484(11) 0.1701(7) 0.5098(5) 0.045(2) Uani 1 1 d . . . H10A H 0.7441 0.2324 0.5546 0.054 Uiso 1 1 calc R . . H10B H 0.8634 0.1785 0.4859 0.054 Uiso 1 1 calc R . . C11 C 0.7470(13) 0.0644(7) 0.5406(5) 0.061(3) Uani 1 1 d . . . H11A H 0.8567 0.0618 0.5807 0.091 Uiso 1 1 calc R . . H11B H 0.7483 0.0031 0.4957 0.091 Uiso 1 1 calc R . . H11C H 0.6351 0.0579 0.5659 0.091 Uiso 1 1 calc R . . C12 C 0.2610(11) 0.5250(5) 0.2705(4) 0.0299(18) Uani 1 1 d . . . C13 C 0.3923(11) 0.6455(7) 0.1933(5) 0.041(2) Uani 1 1 d . . . H13A H 0.4754 0.712 0.2061 0.049 Uiso 1 1 calc R . . H13B H 0.2634 0.6696 0.182 0.049 Uiso 1 1 calc R . . C14 C 0.4424(12) 0.5713(7) 0.1211(5) 0.055(3) Uani 1 1 d . . . H14A H 0.432 0.6112 0.0749 0.082 Uiso 1 1 calc R . . H14B H 0.3582 0.5063 0.1081 0.082 Uiso 1 1 calc R . . H14C H 0.5701 0.5476 0.1326 0.082 Uiso 1 1 calc R . . C15 C 0.5283(9) 0.3389(5) 0.2670(4) 0.0203(15) Uani 1 1 d . . . H15 H 0.6469 0.3635 0.295 0.024 Uiso 1 1 calc R . . C16 C 0.4955(8) 0.2985(5) 0.1880(4) 0.0169(15) Uani 1 1 d . . . C17 C 0.6127(9) 0.2898(5) 0.1257(4) 0.0194(15) Uani 1 1 d . . . C18 C 0.7751(9) 0.3543(6) 0.1365(4) 0.0210(16) Uani 1 1 d . . . H18 H 0.8063 0.4056 0.185 0.025 Uiso 1 1 calc R . . C19 C 0.8923(9) 0.3448(5) 0.0775(4) 0.0246(17) Uani 1 1 d . . . H19 H 1.0041 0.3881 0.0867 0.03 Uiso 1 1 calc R . . C20 C 0.8474(9) 0.2732(6) 0.0060(4) 0.0247(17) Uani 1 1 d . . . C21 C 0.6828(10) 0.2094(6) -0.0070(4) 0.0252(17) Uani 1 1 d . . . C22 C 0.5689(9) 0.2171(5) 0.0517(4) 0.0233(17) Uani 1 1 d . . . H22 H 0.4584 0.1726 0.0423 0.028 Uiso 1 1 calc R . . C23 C 0.0786(10) 0.0903(5) 0.1946(4) 0.0250(17) Uani 1 1 d . . . H23A H 0.1726 0.0537 0.1631 0.03 Uiso 1 1 calc R . . H23B H -0.0136 0.1227 0.1571 0.03 Uiso 1 1 calc R . . C24 C -0.0164(9) 0.0063(5) 0.2329(4) 0.0215(16) Uani 1 1 d . . . C25 C -0.1599(9) 0.0373(6) 0.2778(4) 0.0253(17) Uani 1 1 d . . . H25 H -0.2011 0.1112 0.2831 0.03 Uiso 1 1 calc R . . C26 C -0.2416(9) -0.0385(5) 0.3145(4) 0.0220(16) Uani 1 1 d . . . H26 H -0.3365 -0.0159 0.3464 0.026 Uiso 1 1 calc R . . C27 C -0.1891(9) -0.1462(6) 0.3059(4) 0.0229(16) Uani 1 1 d . . . C28 C -0.0488(10) -0.1806(6) 0.2610(4) 0.0260(17) Uani 1 1 d . . . H28 H -0.0104 -0.255 0.255 0.031 Uiso 1 1 calc R . . C29 C 0.0350(10) -0.1014(6) 0.2244(4) 0.0280(17) Uani 1 1 d . . . H29 H 0.1305 -0.1237 0.1928 0.034 Uiso 1 1 calc R . . C30 C 1.1116(10) 0.3309(7) -0.0481(4) 0.040(2) Uani 1 1 d . . . H30A H 1.1714 0.3151 -0.097 0.059 Uiso 1 1 calc R . . H30B H 1.1984 0.3176 -0.0013 0.059 Uiso 1 1 calc R . . H30C H 1.0754 0.4083 -0.0401 0.059 Uiso 1 1 calc R . . C31 C 0.4728(11) 0.0857(7) -0.1016(4) 0.046(2) Uani 1 1 d . . . H31A H 0.4658 0.0414 -0.1557 0.068 Uiso 1 1 calc R . . H31B H 0.3744 0.1398 -0.1014 0.068 Uiso 1 1 calc R . . H31C H 0.4575 0.0372 -0.0622 0.068 Uiso 1 1 calc R . . C32 C -0.2082(11) -0.3241(6) 0.3462(4) 0.038(2) Uani 1 1 d . . . H32A H -0.283 -0.3651 0.3762 0.057 Uiso 1 1 calc R . . H32B H -0.0792 -0.3187 0.3723 0.057 Uiso 1 1 calc R . . H32C H -0.2142 -0.3628 0.2905 0.057 Uiso 1 1 calc R . . N1 N 0.1673(7) 0.1774(4) 0.2571(3) 0.0202(13) Uani 1 1 d . . . O1 O 0.6418(7) 0.3494(4) 0.4460(3) 0.0375(14) Uani 1 1 d . . . O2 O 0.5865(6) 0.1706(4) 0.4483(3) 0.0302(13) Uani 1 1 d . . . O3 O 0.1127(7) 0.5266(4) 0.2295(3) 0.0332(13) Uani 1 1 d . . . O4 O 0.4100(7) 0.5856(4) 0.2622(3) 0.0380(14) Uani 1 1 d . . . O5 O 0.3128(6) 0.2650(4) 0.1626(2) 0.0233(11) Uani 1 1 d . . . O6 O 0.9506(7) 0.2604(4) -0.0565(3) 0.0368(14) Uani 1 1 d . . . O7 O 0.6486(7) 0.1423(4) -0.0808(3) 0.0362(14) Uani 1 1 d . . . O8 O -0.2781(7) -0.2156(4) 0.3457(3) 0.0347(13) 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 C1 0.020(4) 0.014(3) 0.021(4) 0.012(3) -0.001(3) 0.000(3) C2 0.020(4) 0.030(4) 0.018(4) 0.009(3) 0.001(3) -0.003(3) C3 0.051(5) 0.030(4) 0.018(4) 0.003(3) 0.007(4) -0.010(4) C4 0.040(5) 0.034(4) 0.024(4) 0.009(3) 0.007(4) 0.001(4) C5 0.032(4) 0.020(4) 0.021(4) 0.008(3) -0.001(3) -0.006(3) C6 0.025(4) 0.022(4) 0.012(3) 0.002(3) -0.001(3) -0.005(3) C7 0.024(4) 0.018(4) 0.021(4) 0.003(3) 0.008(3) 0.001(3) C8 0.016(4) 0.016(4) 0.025(4) 0.004(3) -0.002(3) -0.003(3) C9 0.032(4) 0.020(4) 0.016(3) 0.004(3) 0.000(3) 0.001(3) C10 0.032(5) 0.052(5) 0.052(5) 0.031(4) -0.024(4) -0.015(4) C11 0.058(6) 0.071(7) 0.050(6) 0.035(5) -0.030(5) -0.016(5) C12 0.043(5) 0.020(4) 0.025(4) 0.001(3) 0.000(4) -0.014(4) C13 0.034(5) 0.044(5) 0.048(5) 0.030(4) -0.007(4) -0.013(4) C14 0.053(6) 0.071(7) 0.056(6) 0.041(5) 0.024(5) 0.012(5) C15 0.019(4) 0.024(4) 0.017(4) 0.002(3) 0.003(3) -0.003(3) C16 0.010(4) 0.014(3) 0.025(4) 0.004(3) -0.001(3) -0.001(3) C17 0.013(4) 0.021(4) 0.025(4) 0.011(3) 0.000(3) 0.003(3) C18 0.016(4) 0.034(4) 0.012(3) 0.000(3) 0.002(3) -0.005(3) C19 0.020(4) 0.027(4) 0.025(4) 0.007(3) -0.006(3) -0.002(3) C20 0.012(4) 0.039(4) 0.026(4) 0.012(3) 0.005(3) 0.008(3) C21 0.028(4) 0.029(4) 0.015(4) 0.002(3) -0.003(3) -0.011(3) C22 0.021(4) 0.028(4) 0.020(4) 0.009(3) -0.005(3) -0.012(3) C23 0.028(4) 0.025(4) 0.021(4) 0.004(3) 0.000(3) -0.004(3) C24 0.021(4) 0.026(4) 0.016(3) 0.003(3) -0.004(3) -0.007(3) C25 0.021(4) 0.021(4) 0.030(4) 0.002(3) -0.006(3) -0.010(3) C26 0.012(4) 0.028(4) 0.025(4) 0.002(3) 0.003(3) 0.003(3) C27 0.020(4) 0.028(4) 0.020(4) 0.009(3) -0.003(3) -0.010(3) C28 0.028(4) 0.018(4) 0.031(4) 0.004(3) -0.002(4) -0.002(3) C29 0.033(5) 0.027(4) 0.025(4) 0.004(3) 0.008(3) -0.003(3) C30 0.029(5) 0.061(6) 0.033(5) 0.019(4) 0.004(4) -0.011(4) C31 0.052(6) 0.056(6) 0.022(4) -0.002(4) -0.004(4) -0.022(5) C32 0.044(5) 0.035(5) 0.036(5) 0.018(4) -0.005(4) -0.009(4) N1 0.025(3) 0.019(3) 0.015(3) 0.006(2) -0.006(2) -0.006(3) O1 0.046(4) 0.030(3) 0.031(3) 0.010(2) -0.019(3) -0.018(3) O2 0.032(3) 0.029(3) 0.025(3) 0.008(2) -0.017(2) -0.009(2) O3 0.024(3) 0.036(3) 0.038(3) 0.016(2) -0.013(2) -0.009(2) O4 0.036(3) 0.040(3) 0.040(3) 0.025(3) -0.010(3) -0.019(3) O5 0.017(3) 0.035(3) 0.018(2) 0.007(2) 0.000(2) -0.009(2) O6 0.036(3) 0.057(4) 0.018(3) 0.009(2) 0.002(2) -0.012(3) O7 0.036(3) 0.053(3) 0.016(3) -0.004(2) 0.001(2) -0.018(3) O8 0.035(3) 0.040(3) 0.033(3) 0.018(3) 0.001(2) -0.012(3) #----------------------------------------------------------------------------# # MOLECULAR GEOMETRY # #----------------------------------------------------------------------------# _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 C1 C9 1.519(9) . ? C1 C8 1.543(8) . ? C1 C2 1.560(9) . ? C1 C6 1.575(8) . ? C2 C3 1.495(9) . ? C3 C4 1.525(9) . ? C4 C5 1.511(9) . ? C5 C12 1.523(9) . ? C5 C6 1.534(9) . ? C6 C15 1.514(9) . ? C6 C7 1.565(8) . ? C7 N1 1.419(7) . ? C7 O5 1.469(7) . ? C8 N1 1.469(8) . ? C9 O1 1.200(7) . ? C9 O2 1.320(7) . ? C10 O2 1.465(8) . ? C10 C11 1.473(10) . ? C12 O3 1.205(8) . ? C12 O4 1.347(8) . ? C13 O4 1.466(8) . ? C13 C14 1.491(11) . ? C15 C16 1.337(8) . ? C16 O5 1.381(7) . ? C16 C17 1.435(9) . ? C17 C18 1.394(9) . ? C17 C22 1.412(9) . ? C18 C19 1.391(9) . ? C19 C20 1.374(9) . ? C20 O6 1.368(8) . ? C20 C21 1.400(9) . ? C21 C22 1.370(9) . ? C21 O7 1.372(8) . ? C23 N1 1.456(8) . ? C23 C24 1.513(8) . ? C24 C29 1.365(9) . ? C24 C25 1.395(9) . ? C25 C26 1.372(9) . ? C26 C27 1.368(9) . ? C27 O8 1.376(7) . ? C27 C28 1.383(10) . ? C28 C29 1.409(9) . ? C30 O6 1.430(8) . ? C31 O7 1.426(8) . ? C32 O8 1.428(8) . ? 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 C9 C1 C8 113.9(5) . . ? C9 C1 C2 107.6(5) . . ? C8 C1 C2 108.8(5) . . ? C9 C1 C6 112.9(5) . . ? C8 C1 C6 101.5(5) . . ? C2 C1 C6 112.2(5) . . ? C3 C2 C1 114.9(5) . . ? C2 C3 C4 110.2(6) . . ? C5 C4 C3 110.2(6) . . ? C4 C5 C12 109.9(6) . . ? C4 C5 C6 113.3(5) . . ? C12 C5 C6 109.9(5) . . ? C15 C6 C5 111.7(5) . . ? C15 C6 C7 99.9(5) . . ? C5 C6 C7 115.8(5) . . ? C15 C6 C1 111.2(5) . . ? C5 C6 C1 114.3(5) . . ? C7 C6 C1 102.8(5) . . ? N1 C7 O5 113.5(5) . . ? N1 C7 C6 105.8(5) . . ? O5 C7 C6 106.9(5) . . ? N1 C8 C1 99.9(5) . . ? O1 C9 O2 124.8(6) . . ? O1 C9 C1 123.9(6) . . ? O2 C9 C1 110.8(5) . . ? O2 C10 C11 108.5(6) . . ? O3 C12 O4 123.3(6) . . ? O3 C12 C5 125.3(6) . . ? O4 C12 C5 111.4(6) . . ? O4 C13 C14 109.1(6) . . ? C16 C15 C6 111.8(6) . . ? C15 C16 O5 112.8(6) . . ? C15 C16 C17 131.6(6) . . ? O5 C16 C17 115.6(5) . . ? C18 C17 C22 117.5(6) . . ? C18 C17 C16 120.5(6) . . ? C22 C17 C16 122.0(6) . . ? C19 C18 C17 121.2(6) . . ? C20 C19 C18 120.4(6) . . ? O6 C20 C19 124.8(6) . . ? O6 C20 C21 115.8(6) . . ? C19 C20 C21 119.4(6) . . ? C22 C21 O7 124.8(6) . . ? C22 C21 C20 120.3(6) . . ? O7 C21 C20 115.0(6) . . ? C21 C22 C17 121.3(6) . . ? N1 C23 C24 109.8(5) . . ? C29 C24 C25 118.3(6) . . ? C29 C24 C23 121.3(6) . . ? C25 C24 C23 120.4(6) . . ? C26 C25 C24 120.1(7) . . ? C27 C26 C25 121.2(7) . . ? C26 C27 O8 116.8(6) . . ? C26 C27 C28 120.4(6) . . ? O8 C27 C28 122.8(6) . . ? C27 C28 C29 117.7(7) . . ? C24 C29 C28 122.2(7) . . ? C7 N1 C23 118.0(5) . . ? C7 N1 C8 108.5(5) . . ? C23 N1 C8 117.6(5) . . ? C9 O2 C10 116.4(5) . . ? C12 O4 C13 116.7(5) . . ? C16 O5 C7 107.9(5) . . ? C20 O6 C30 117.2(6) . . ? C21 O7 C31 117.6(6) . . ? C27 O8 C32 117.3(6) . . ? 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 C9 C1 C2 C3 80.8(7) . . . . ? C8 C1 C2 C3 -155.4(5) . . . . ? C6 C1 C2 C3 -43.9(7) . . . . ? C1 C2 C3 C4 56.1(8) . . . . ? C2 C3 C4 C5 -61.9(8) . . . . ? C3 C4 C5 C12 -179.2(6) . . . . ? C3 C4 C5 C6 57.4(8) . . . . ? C4 C5 C6 C15 -173.4(5) . . . . ? C12 C5 C6 C15 63.3(7) . . . . ? C4 C5 C6 C7 73.2(7) . . . . ? C12 C5 C6 C7 -50.2(8) . . . . ? C4 C5 C6 C1 -46.0(8) . . . . ? C12 C5 C6 C1 -169.4(6) . . . . ? C9 C1 C6 C15 43.8(7) . . . . ? C8 C1 C6 C15 -78.5(6) . . . . ? C2 C1 C6 C15 165.5(5) . . . . ? C9 C1 C6 C5 -83.8(7) . . . . ? C8 C1 C6 C5 153.9(5) . . . . ? C2 C1 C6 C5 37.9(7) . . . . ? C9 C1 C6 C7 149.9(5) . . . . ? C8 C1 C6 C7 27.6(6) . . . . ? C2 C1 C6 C7 -88.4(6) . . . . ? C15 C6 C7 N1 113.1(5) . . . . ? C5 C6 C7 N1 -126.8(6) . . . . ? C1 C6 C7 N1 -1.4(7) . . . . ? C15 C6 C7 O5 -8.2(6) . . . . ? C5 C6 C7 O5 111.9(6) . . . . ? C1 C6 C7 O5 -122.7(5) . . . . ? C9 C1 C8 N1 -164.8(5) . . . . ? C2 C1 C8 N1 75.3(6) . . . . ? C6 C1 C8 N1 -43.2(6) . . . . ? C8 C1 C9 O1 150.1(7) . . . . ? C2 C1 C9 O1 -89.3(8) . . . . ? C6 C1 C9 O1 35.0(10) . . . . ? C8 C1 C9 O2 -37.3(7) . . . . ? C2 C1 C9 O2 83.3(7) . . . . ? C6 C1 C9 O2 -152.4(5) . . . . ? C4 C5 C12 O3 -39.8(10) . . . . ? C6 C5 C12 O3 85.5(9) . . . . ? C4 C5 C12 O4 138.0(6) . . . . ? C6 C5 C12 O4 -96.7(7) . . . . ? C5 C6 C15 C16 -116.5(6) . . . . ? C7 C6 C15 C16 6.5(7) . . . . ? C1 C6 C15 C16 114.4(6) . . . . ? C6 C15 C16 O5 -2.2(7) . . . . ? C6 C15 C16 C17 174.0(6) . . . . ? C15 C16 C17 C18 -18.9(10) . . . . ? O5 C16 C17 C18 157.2(5) . . . . ? C15 C16 C17 C22 161.5(7) . . . . ? O5 C16 C17 C22 -22.4(8) . . . . ? C22 C17 C18 C19 -1.9(9) . . . . ? C16 C17 C18 C19 178.4(6) . . . . ? C17 C18 C19 C20 1.7(10) . . . . ? C18 C19 C20 O6 178.0(6) . . . . ? C18 C19 C20 C21 -0.2(10) . . . . ? O6 C20 C21 C22 -179.4(6) . . . . ? C19 C20 C21 C22 -1.0(10) . . . . ? O6 C20 C21 O7 0.3(9) . . . . ? C19 C20 C21 O7 178.7(6) . . . . ? O7 C21 C22 C17 -178.9(6) . . . . ? C20 C21 C22 C17 0.8(10) . . . . ? C18 C17 C22 C21 0.7(9) . . . . ? C16 C17 C22 C21 -179.7(6) . . . . ? N1 C23 C24 C29 -118.3(7) . . . . ? N1 C23 C24 C25 61.9(8) . . . . ? C29 C24 C25 C26 2.2(9) . . . . ? C23 C24 C25 C26 -178.0(6) . . . . ? C24 C25 C26 C27 -2.1(10) . . . . ? C25 C26 C27 O8 179.4(6) . . . . ? C25 C26 C27 C28 1.3(10) . . . . ? C26 C27 C28 C29 -0.6(10) . . . . ? O8 C27 C28 C29 -178.6(5) . . . . ? C25 C24 C29 C28 -1.5(10) . . . . ? C23 C24 C29 C28 178.6(6) . . . . ? C27 C28 C29 C24 0.8(10) . . . . ? O5 C7 N1 C23 -47.7(8) . . . . ? C6 C7 N1 C23 -164.6(6) . . . . ? O5 C7 N1 C8 89.3(6) . . . . ? C6 C7 N1 C8 -27.7(7) . . . . ? C24 C23 N1 C7 -161.7(6) . . . . ? C24 C23 N1 C8 65.2(7) . . . . ? C1 C8 N1 C7 45.4(6) . . . . ? C1 C8 N1 C23 -177.4(5) . . . . ? O1 C9 O2 C10 1.2(11) . . . . ? C1 C9 O2 C10 -171.3(6) . . . . ? C11 C10 O2 C9 170.0(7) . . . . ? O3 C12 O4 C13 -7.2(11) . . . . ? C5 C12 O4 C13 174.9(6) . . . . ? C14 C13 O4 C12 -87.1(8) . . . . ? C15 C16 O5 C7 -3.6(7) . . . . ? C17 C16 O5 C7 179.5(5) . . . . ? N1 C7 O5 C16 -108.6(6) . . . . ? C6 C7 O5 C16 7.6(6) . . . . ? C19 C20 O6 C30 -3.4(9) . . . . ? C21 C20 O6 C30 174.9(6) . . . . ? C22 C21 O7 C31 7.4(10) . . . . ? C20 C21 O7 C31 -172.4(6) . . . . ? C26 C27 O8 C32 -171.8(6) . . . . ? C28 C27 O8 C32 6.2(9) . . . . ? #===END