Supplementary Material for Organic & Biomolecular Chemistry This journal is © The Royal Society of Chemistry 2005 data_GLOBAL _journal_name_full Org.Biomol.Chem. _journal_coden_Cambridge 0177 # 1. SUBMISSION DETAILS _publ_contact_author_name 'Thomas Muller' _publ_contact_author_address ; Organisch-Chemisches Institut Universit\"at Heidelberg Im Neuenheimer Feld 270 D-69120 Heidelberg Germany ; _publ_contact_author_phone '049 6221 54-6207' _publ_contact_author_fax '049 6221 54-4205' _publ_contact_author_email 'Thomas J.J.Mueller@urz.uni-heidelberg.de' _publ_requested_coeditor_name ? _publ_contact_letter ; paper submitted for publication Organic & Biomolecular Chemistry ; #======================================================================== # 3. TITLE AND AUTHOR LIST _publ_section_title ; A diversity oriented four-component approach to tetrahydro-\b-carbolines initiated by Sonogashira coupling; ; loop_ _publ_author_name _publ_author_address 'Alexei S. Karpov' ; Organisch-Chemisches Institut Universit\"at Heidelberg Im Neuenheimer Feld 270 69120 Heidelberg Bundesrepublik Deutschland ; F.Rominger ; Organisch-Chemisches Institut Universit\"at Heidelberg Im Neuenheimer Feld 270 69120 Heidelberg Bundesrepublik Deutschland ; T.J.J.Muller ; Organisch-Chemisches Institut Universit\"at Heidelberg Im Neuenheimer Feld 270 69120 Heidelberg Bundesrepublik Deutschland ; #===================================================================== data_aka6 _database_code_depnum_ccdc_archive 'CCDC 281672' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common '6a in paper' _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C25 H28 Cl2 N2 O2 S' _chemical_formula_weight 491.45 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' S S 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Orthorhombic _symmetry_space_group_name_H-M Pna2(1) 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' _cell_length_a 24.2176(8) _cell_length_b 14.5820(5) _cell_length_c 14.2040(5) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 5016.0(3) _cell_formula_units_Z 8 _cell_measurement_temperature 200(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description polyhedron _exptl_crystal_colour colorless _exptl_crystal_size_max 0.34 _exptl_crystal_size_mid 0.34 _exptl_crystal_size_min 0.18 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.302 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 2064 _exptl_absorpt_coefficient_mu 0.366 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.8856 _exptl_absorpt_correction_T_max 0.9370 _exptl_absorpt_process_details 'Blessing, Acta Cryst. (1995) A51 33-38.' _exptl_special_details ; ? ; _diffrn_ambient_temperature 200(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'CCD area detector' _diffrn_measurement_method 'phi and omega scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 31357 _diffrn_reflns_av_R_equivalents 0.0396 _diffrn_reflns_av_sigmaI/netI 0.0295 _diffrn_reflns_limit_h_min -25 _diffrn_reflns_limit_h_max 25 _diffrn_reflns_limit_k_min -15 _diffrn_reflns_limit_k_max 15 _diffrn_reflns_limit_l_min -14 _diffrn_reflns_limit_l_max 14 _diffrn_reflns_theta_min 1.63 _diffrn_reflns_theta_max 21.96 _reflns_number_total 6126 _reflns_number_gt 5352 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'Bruker SMART' _computing_data_reduction 'Bruker SHELXTL' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Bruker SHELXTL' _computing_publication_material 'Bruker SHELXTL' _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0872P)^2^+5.5621P] 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_extinction_coef ? _refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881' _refine_ls_abs_structure_Flack 0.0(3) _refine_ls_number_reflns 6126 _refine_ls_number_parameters 578 _refine_ls_number_restraints 8 _refine_ls_R_factor_all 0.0688 _refine_ls_R_factor_gt 0.0588 _refine_ls_wR_factor_ref 0.1612 _refine_ls_wR_factor_gt 0.1529 _refine_ls_goodness_of_fit_ref 1.066 _refine_ls_restrained_S_all 1.065 _refine_ls_shift/su_max 0.008 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group S1_1 S -0.16710(10) -0.69831(16) -0.83442(15) 0.0970(7) Uani 1 1 d . . . C2_1 C -0.2273(4) -0.6719(8) -0.7841(8) 0.119(4) Uani 1 1 d . . . H2_1 H -0.2618 -0.6930 -0.8076 0.143 Uiso 1 1 calc R . . C3_1 C -0.2225(4) -0.6161(9) -0.7046(8) 0.120(4) Uani 1 1 d . . . H3_1 H -0.2529 -0.5950 -0.6682 0.144 Uiso 1 1 calc R . . C4_1 C -0.1677(2) -0.5956(5) -0.6854(5) 0.0634(17) Uani 1 1 d . . . H4_1 H -0.1558 -0.5586 -0.6342 0.076 Uiso 1 1 calc R . . C5_1 C -0.1315(3) -0.6372(4) -0.7521(4) 0.0581(17) Uani 1 1 d . . . C6_1 C -0.0710(3) -0.6344(3) -0.7593(4) 0.0448(14) Uani 1 1 d . . . O6_1 O -0.04754(19) -0.6709(3) -0.8244(3) 0.0622(11) Uani 1 1 d . . . C7_1 C -0.0394(2) -0.5880(3) -0.6798(4) 0.0386(12) Uani 1 1 d . . . H7_1 H -0.0657 -0.5765 -0.6268 0.046 Uiso 1 1 calc R . . C8_1 C -0.0131(2) -0.4942(3) -0.7092(3) 0.0315(11) Uani 1 1 d . . . C9_1 C -0.0585(2) -0.4302(3) -0.7395(3) 0.0301(11) Uani 1 1 d . . . N10_1 N -0.08475(16) -0.4358(3) -0.8265(3) 0.0333(9) Uani 1 1 d . . . H10_1 H -0.0774 -0.4760 -0.8709 0.040 Uiso 1 1 calc R . . C11_1 C -0.12389(19) -0.3684(3) -0.8314(4) 0.0349(12) Uani 1 1 d . . . C12_1 C -0.1599(2) -0.3454(4) -0.9032(4) 0.0470(14) Uani 1 1 d . . . H12_1 H -0.1612 -0.3797 -0.9600 0.056 Uiso 1 1 calc R . . C13_1 C -0.1940(2) -0.2702(4) -0.8889(5) 0.0590(17) Uani 1 1 d . . . H13_1 H -0.2188 -0.2527 -0.9375 0.071 Uiso 1 1 calc R . . C14_1 C -0.1934(3) -0.2202(4) -0.8065(5) 0.0589(17) Uani 1 1 d . . . H14_1 H -0.2181 -0.1701 -0.7990 0.071 Uiso 1 1 calc R . . C15_1 C -0.1576(2) -0.2420(4) -0.7355(5) 0.0504(15) Uani 1 1 d . . . H15_1 H -0.1567 -0.2063 -0.6796 0.061 Uiso 1 1 calc R . . C16_1 C -0.1221(2) -0.3181(3) -0.7461(4) 0.0377(12) Uani 1 1 d . . . C17_1 C -0.0798(2) -0.3590(3) -0.6894(3) 0.0340(12) Uani 1 1 d . . . C18_1 C -0.0546(2) -0.3292(4) -0.5987(4) 0.0471(14) Uani 1 1 d . . . H18A_1 H -0.0738 -0.3588 -0.5452 0.057 Uiso 1 1 calc R . . H18B_1 H -0.0579 -0.2619 -0.5916 0.057 Uiso 1 1 calc R . . C19_1 C 0.0053(2) -0.3569(3) -0.5999(4) 0.0431(14) Uani 1 1 d . . . H19A_1 H 0.0251 -0.3208 -0.6483 0.052 Uiso 1 1 calc R . . H19B_1 H 0.0222 -0.3432 -0.5380 0.052 Uiso 1 1 calc R . . N20_1 N 0.01127(17) -0.4565(3) -0.6208(3) 0.0357(10) Uani 1 1 d . . . C21_1 C 0.0406(2) -0.5073(3) -0.5607(4) 0.0370(12) Uani 1 1 d . . . O21_1 O 0.06614(17) -0.4723(2) -0.4943(3) 0.0510(10) Uani 1 1 d . . . C22_1 C 0.0420(3) -0.6105(4) -0.5717(4) 0.0505(14) Uani 1 1 d . . . H22A_1 H 0.0328 -0.6379 -0.5099 0.061 Uiso 1 1 calc R . . H22B_1 H 0.0805 -0.6283 -0.5866 0.061 Uiso 1 1 calc R . . C23_1 C 0.0044(2) -0.6545(3) -0.6456(4) 0.0472(14) Uani 1 1 d . . . H23A_1 H 0.0270 -0.6750 -0.6997 0.057 Uiso 1 1 calc R . . H23B_1 H -0.0137 -0.7091 -0.6180 0.057 Uiso 1 1 calc R . . C24_1 C 0.0313(2) -0.5053(3) -0.7862(4) 0.0371(12) Uani 1 1 d . . . H24A_1 H 0.0594 -0.5495 -0.7636 0.045 Uiso 1 1 calc R . . H24B_1 H 0.0138 -0.5322 -0.8428 0.045 Uiso 1 1 calc R . . C25_1 C 0.0603(3) -0.4178(4) -0.8145(4) 0.0514(15) Uani 1 1 d . . . H25A_1 H 0.0787 -0.3915 -0.7585 0.062 Uiso 1 1 calc R . . H25B_1 H 0.0323 -0.3730 -0.8363 0.062 Uiso 1 1 calc R . . C26_1 C 0.1029(3) -0.4310(4) -0.8916(4) 0.0613(17) Uani 1 1 d . . . H26A_1 H 0.1299 -0.4778 -0.8709 0.074 Uiso 1 1 calc R . . H26B_1 H 0.0841 -0.4550 -0.9484 0.074 Uiso 1 1 calc R . . C27_1 C 0.1333(4) -0.3457(6) -0.9174(7) 0.108(3) Uani 1 1 d . . . H27A_1 H 0.1598 -0.3594 -0.9677 0.162 Uiso 1 1 calc R . . H27B_1 H 0.1532 -0.3226 -0.8622 0.162 Uiso 1 1 calc R . . H27C_1 H 0.1071 -0.2993 -0.9393 0.162 Uiso 1 1 calc R . . S1_2 S 0.16985(11) -1.14771(17) -0.67860(18) 0.1082(9) Uani 1 1 d . . . C2_2 C 0.2236(3) -1.1047(8) -0.7425(9) 0.121(4) Uani 1 1 d . . . H2_2 H 0.2612 -1.1135 -0.7262 0.146 Uiso 1 1 calc R . . C3_2 C 0.2069(3) -1.0569(8) -0.8185(7) 0.107(3) Uani 1 1 d . . . H3_2 H 0.2310 -1.0263 -0.8608 0.128 Uiso 1 1 calc R . . C4_2 C 0.1502(3) -1.0584(5) -0.8266(5) 0.0681(18) Uani 1 1 d . . . H4_2 H 0.1314 -1.0291 -0.8770 0.082 Uiso 1 1 calc R . . C5_2 C 0.1225(3) -1.1051(4) -0.7567(5) 0.0634(19) Uani 1 1 d . . . C6_2 C 0.0633(3) -1.1168(4) -0.7399(5) 0.0554(17) Uani 1 1 d . . . O6_2 O 0.0460(2) -1.1517(3) -0.6664(4) 0.0757(14) Uani 1 1 d . . . C7_2 C 0.0241(2) -1.0889(3) -0.8163(4) 0.0416(13) Uani 1 1 d . . . H7_2 H 0.0466 -1.0774 -0.8741 0.050 Uiso 1 1 calc R . . C8_2 C -0.0089(2) -0.9984(3) -0.7949(3) 0.0341(12) Uani 1 1 d . . . C9_2 C 0.0324(2) -0.9224(3) -0.7780(3) 0.0321(11) Uani 1 1 d . . . N10_2 N 0.06344(16) -0.9147(3) -0.6973(3) 0.0335(10) Uani 1 1 d . . . H10_2 H 0.0612 -0.9509 -0.6479 0.040 Uiso 1 1 calc R . . C11_2 C 0.09880(19) -0.8408(3) -0.7065(3) 0.0321(12) Uani 1 1 d . . . C12_2 C 0.1368(2) -0.8045(3) -0.6442(4) 0.0391(13) Uani 1 1 d . . . H12_2 H 0.1427 -0.8314 -0.5842 0.047 Uiso 1 1 calc R . . C13_2 C 0.1659(2) -0.7275(4) -0.6724(4) 0.0450(13) Uani 1 1 d . . . H13_2 H 0.1922 -0.7007 -0.6311 0.054 Uiso 1 1 calc R . . C14_2 C 0.1568(2) -0.6888(3) -0.7613(4) 0.0450(14) Uani 1 1 d . . . H14_2 H 0.1770 -0.6357 -0.7786 0.054 Uiso 1 1 calc R . . C15_2 C 0.1198(2) -0.7248(3) -0.8241(4) 0.0433(13) Uani 1 1 d . . . H15_2 H 0.1147 -0.6977 -0.8843 0.052 Uiso 1 1 calc R . . C16_2 C 0.0898(2) -0.8023(3) -0.7976(3) 0.0352(12) Uani 1 1 d . . . C17_2 C 0.0470(2) -0.8561(3) -0.8408(3) 0.0332(12) Uani 1 1 d . . . C18_2 C 0.0156(2) -0.8405(3) -0.9303(4) 0.0400(13) Uani 1 1 d . . . H18A_2 H 0.0341 -0.8718 -0.9835 0.048 Uiso 1 1 calc R . . H18B_2 H 0.0136 -0.7741 -0.9446 0.048 Uiso 1 1 calc R . . C19_2 C -0.0416(2) -0.8791(3) -0.9158(4) 0.0384(13) Uani 1 1 d . . . H19A_2 H -0.0614 -0.8421 -0.8681 0.046 Uiso 1 1 calc R . . H19B_2 H -0.0626 -0.8755 -0.9755 0.046 Uiso 1 1 calc R . . N20_2 N -0.03880(17) -0.9759(2) -0.8841(3) 0.0349(10) Uani 1 1 d . . . C21_2 C -0.0619(2) -1.0411(4) -0.9390(4) 0.0383(13) Uani 1 1 d . . . O21_2 O -0.08772(16) -1.0202(2) -1.0116(2) 0.0451(9) Uani 1 1 d . . . C22_2 C -0.0563(3) -1.1407(4) -0.9143(4) 0.0559(16) Uani 1 1 d . . . H22A_2 H -0.0463 -1.1741 -0.9726 0.067 Uiso 1 1 calc R . . H22B_2 H -0.0931 -1.1631 -0.8946 0.067 Uiso 1 1 calc R . . C23_2 C -0.0152(2) -1.1679(3) -0.8386(4) 0.0504(14) Uani 1 1 d . . . H23A_2 H 0.0063 -1.2217 -0.8601 0.060 Uiso 1 1 calc R . . H23B_2 H -0.0354 -1.1857 -0.7808 0.060 Uiso 1 1 calc R . . C24_2 C -0.0487(2) -1.0098(4) -0.7126(4) 0.0433(13) Uani 1 1 d . . . H24A_2 H -0.0273 -1.0283 -0.6564 0.052 Uiso 1 1 calc R . . H24B_2 H -0.0746 -1.0604 -0.7276 0.052 Uiso 1 1 calc R . . C25_2 C -0.0825(3) -0.9246(4) -0.6879(4) 0.0545(15) Uani 1 1 d . . . H25A_2 H -0.0571 -0.8735 -0.6728 0.065 Uiso 1 1 calc R . . H25B_2 H -0.1047 -0.9062 -0.7434 0.065 Uiso 1 1 calc R . . C26_2 C -0.1210(3) -0.9401(5) -0.6049(5) 0.080(2) Uani 1 1 d . . . H26A_2 H -0.0987 -0.9507 -0.5475 0.096 Uiso 1 1 calc R . . H26B_2 H -0.1433 -0.9959 -0.6165 0.096 Uiso 1 1 calc R . . C27_2 C -0.1595(4) -0.8590(6) -0.5885(7) 0.114(3) Uani 1 1 d . . . H27A_2 H -0.1843 -0.8727 -0.5358 0.171 Uiso 1 1 calc R . . H27B_2 H -0.1814 -0.8478 -0.6454 0.171 Uiso 1 1 calc R . . H27C_2 H -0.1377 -0.8043 -0.5737 0.171 Uiso 1 1 calc R . . C51 C -0.1871(4) -0.6067(7) -1.0654(8) 0.120(3) Uani 1 1 d D . . H51A H -0.1629 -0.6580 -1.0849 0.144 Uiso 1 1 calc R . . H51B H -0.1712 -0.5803 -1.0071 0.144 Uiso 1 1 calc R . . Cl1 Cl -0.24967(15) -0.6500(4) -1.0393(2) 0.189(2) Uani 1 1 d D . . Cl2 Cl -0.18484(16) -0.5256(2) -1.1500(3) 0.1628(14) Uani 1 1 d D . . C52 C 0.2149(5) -1.0436(14) -0.4601(7) 0.208(9) Uani 1 1 d D . . H52A H 0.2079 -0.9824 -0.4878 0.249 Uiso 1 1 calc R . . H52B H 0.1859 -1.0854 -0.4839 0.249 Uiso 1 1 calc R . . Cl3 Cl 0.20784(14) -1.0352(2) -0.3424(2) 0.1329(10) Uani 1 1 d D . . Cl4 Cl 0.27719(12) -1.0816(3) -0.5003(2) 0.1507(13) Uani 1 1 d 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 S1_1 0.1135(17) 0.1011(15) 0.0763(13) 0.0127(12) -0.0298(13) -0.0549(13) C2_1 0.069(5) 0.165(10) 0.122(8) 0.067(8) -0.031(6) -0.060(6) C3_1 0.086(7) 0.161(10) 0.113(8) 0.025(7) -0.016(6) -0.046(6) C4_1 0.042(3) 0.070(4) 0.079(5) 0.008(4) 0.007(4) -0.019(3) C5_1 0.070(4) 0.048(3) 0.056(4) 0.014(3) -0.024(4) -0.022(3) C6_1 0.071(4) 0.021(3) 0.043(3) 0.000(3) -0.012(3) -0.001(3) O6_1 0.098(3) 0.036(2) 0.052(3) -0.015(2) -0.007(2) 0.004(2) C7_1 0.052(3) 0.027(3) 0.037(3) -0.002(2) 0.002(3) -0.001(2) C8_1 0.050(3) 0.023(2) 0.022(2) -0.0014(19) -0.002(2) 0.000(2) C9_1 0.039(3) 0.024(2) 0.028(3) -0.005(2) 0.001(2) -0.002(2) N10_1 0.043(2) 0.028(2) 0.030(2) -0.0085(18) 0.004(2) 0.0002(19) C11_1 0.033(3) 0.032(3) 0.040(3) 0.001(2) 0.003(2) 0.000(2) C12_1 0.039(3) 0.056(4) 0.046(3) 0.001(3) 0.003(3) -0.001(3) C13_1 0.029(3) 0.071(4) 0.077(5) 0.018(4) -0.002(3) 0.008(3) C14_1 0.051(4) 0.048(4) 0.078(5) 0.001(4) 0.010(4) 0.013(3) C15_1 0.049(3) 0.038(3) 0.064(4) -0.003(3) 0.000(3) 0.009(3) C16_1 0.037(3) 0.034(3) 0.041(3) -0.007(2) 0.005(3) 0.000(2) C17_1 0.046(3) 0.024(2) 0.032(3) -0.003(2) 0.003(2) 0.004(2) C18_1 0.060(4) 0.045(3) 0.037(3) -0.015(3) 0.000(3) 0.010(3) C19_1 0.070(4) 0.025(3) 0.034(3) -0.009(2) -0.012(3) -0.002(3) N20_1 0.050(3) 0.025(2) 0.032(2) -0.0050(19) -0.002(2) -0.0032(19) C21_1 0.049(3) 0.030(3) 0.032(3) 0.005(2) 0.004(3) 0.001(3) O21_1 0.076(3) 0.044(2) 0.033(2) 0.0056(18) -0.017(2) -0.008(2) C22_1 0.065(4) 0.038(3) 0.049(3) 0.008(3) -0.011(3) 0.001(3) C23_1 0.064(4) 0.024(3) 0.053(4) 0.002(2) -0.004(3) 0.001(3) C24_1 0.045(3) 0.033(3) 0.034(3) 0.002(2) 0.003(2) 0.008(2) C25_1 0.062(4) 0.039(3) 0.053(4) -0.002(3) 0.012(3) 0.008(3) C26_1 0.075(4) 0.060(4) 0.049(4) 0.003(3) 0.023(3) -0.001(3) C27_1 0.128(7) 0.088(6) 0.107(7) 0.012(5) 0.070(6) -0.025(5) S1_2 0.1182(19) 0.1030(16) 0.1035(17) -0.0275(14) -0.0578(16) 0.0571(14) C2_2 0.044(4) 0.184(10) 0.136(9) -0.073(8) -0.015(5) 0.048(6) C3_2 0.056(5) 0.174(9) 0.091(6) -0.053(7) -0.020(5) 0.016(5) C4_2 0.054(4) 0.093(5) 0.058(4) -0.024(4) -0.005(4) 0.011(4) C5_2 0.067(4) 0.056(4) 0.067(4) -0.022(4) -0.034(4) 0.021(3) C6_2 0.082(5) 0.022(3) 0.062(4) -0.003(3) -0.026(4) 0.004(3) O6_2 0.119(4) 0.047(2) 0.062(3) 0.018(2) -0.033(3) -0.014(2) C7_2 0.058(3) 0.028(3) 0.038(3) 0.001(2) -0.002(3) -0.001(2) C8_2 0.046(3) 0.023(2) 0.034(3) 0.001(2) -0.002(2) -0.004(2) C9_2 0.046(3) 0.024(3) 0.026(3) 0.004(2) 0.003(2) 0.001(2) N10_2 0.047(2) 0.027(2) 0.026(2) -0.0002(18) 0.003(2) -0.0077(19) C11_2 0.036(3) 0.028(3) 0.032(3) 0.002(2) 0.008(2) 0.003(2) C12_2 0.042(3) 0.036(3) 0.039(3) -0.003(2) 0.001(3) 0.002(2) C13_2 0.035(3) 0.052(3) 0.048(3) -0.007(3) 0.001(3) -0.007(3) C14_2 0.045(3) 0.031(3) 0.059(4) -0.005(3) 0.016(3) -0.009(2) C15_2 0.050(3) 0.027(3) 0.053(3) 0.008(3) 0.009(3) -0.004(2) C16_2 0.039(3) 0.032(3) 0.034(3) 0.003(2) 0.007(2) 0.003(2) C17_2 0.050(3) 0.023(3) 0.027(3) 0.001(2) 0.007(2) 0.000(2) C18_2 0.061(4) 0.028(3) 0.031(3) 0.007(2) 0.001(3) -0.003(2) C19_2 0.057(3) 0.028(3) 0.030(3) 0.002(2) -0.007(2) 0.003(2) N20_2 0.052(3) 0.024(2) 0.029(2) 0.0025(18) -0.004(2) -0.005(2) C21_2 0.050(3) 0.040(3) 0.025(3) -0.005(2) 0.002(3) -0.003(3) O21_2 0.063(2) 0.040(2) 0.032(2) -0.0077(16) -0.0039(19) 0.0005(18) C22_2 0.071(4) 0.036(3) 0.060(4) -0.006(3) -0.015(3) -0.009(3) C23_2 0.069(4) 0.030(3) 0.052(4) -0.001(3) -0.009(3) -0.010(3) C24_2 0.057(3) 0.041(3) 0.032(3) 0.007(2) 0.001(3) -0.010(3) C25_2 0.066(4) 0.058(4) 0.040(3) -0.004(3) 0.010(3) 0.001(3) C26_2 0.099(5) 0.083(5) 0.059(4) 0.005(4) 0.031(4) 0.014(4) C27_2 0.145(8) 0.107(7) 0.090(6) 0.000(5) 0.055(6) 0.026(6) C51 0.131(8) 0.110(7) 0.119(8) 0.043(6) -0.019(7) -0.034(6) Cl1 0.148(3) 0.307(5) 0.113(2) 0.047(3) -0.0485(19) -0.118(3) Cl2 0.191(3) 0.158(3) 0.139(2) 0.080(2) -0.023(2) -0.020(2) C52 0.133(10) 0.40(3) 0.091(8) -0.047(11) -0.020(7) 0.116(13) Cl3 0.162(3) 0.128(2) 0.108(2) -0.0129(17) -0.0052(19) 0.0269(19) Cl4 0.1029(18) 0.248(4) 0.1016(18) 0.003(2) -0.0227(15) 0.018(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 S1_1 C2_1 1.668(11) . ? S1_1 C5_1 1.705(6) . ? C2_1 C3_1 1.397(15) . ? C3_1 C4_1 1.387(11) . ? C4_1 C5_1 1.427(10) . ? C5_1 C6_1 1.469(9) . ? C6_1 O6_1 1.209(7) . ? C6_1 C7_1 1.522(8) . ? C7_1 C23_1 1.516(7) . ? C7_1 C8_1 1.565(7) . ? C8_1 N20_1 1.492(6) . ? C8_1 C9_1 1.505(7) . ? C8_1 C24_1 1.544(7) . ? C9_1 C17_1 1.361(7) . ? C9_1 N10_1 1.392(6) . ? N10_1 C11_1 1.367(6) . ? C11_1 C12_1 1.382(8) . ? C11_1 C16_1 1.417(7) . ? C12_1 C13_1 1.388(8) . ? C13_1 C14_1 1.379(9) . ? C14_1 C15_1 1.367(9) . ? C15_1 C16_1 1.412(7) . ? C16_1 C17_1 1.432(7) . ? C17_1 C18_1 1.490(7) . ? C18_1 C19_1 1.507(8) . ? C19_1 N20_1 1.490(6) . ? N20_1 C21_1 1.335(6) . ? C21_1 O21_1 1.238(6) . ? C21_1 C22_1 1.514(7) . ? C22_1 C23_1 1.529(8) . ? C24_1 C25_1 1.511(8) . ? C25_1 C26_1 1.517(8) . ? C26_1 C27_1 1.491(10) . ? S1_2 C2_2 1.706(12) . ? S1_2 C5_2 1.712(6) . ? C2_2 C3_2 1.346(15) . ? C3_2 C4_2 1.379(10) . ? C4_2 C5_2 1.377(10) . ? C5_2 C6_2 1.465(10) . ? C6_2 O6_2 1.234(8) . ? C6_2 C7_2 1.499(8) . ? C7_2 C23_2 1.528(7) . ? C7_2 C8_2 1.572(7) . ? C8_2 N20_2 1.496(7) . ? C8_2 C9_2 1.512(7) . ? C8_2 C24_2 1.524(7) . ? C9_2 C17_2 1.361(6) . ? C9_2 N10_2 1.376(6) . ? N10_2 C11_2 1.383(6) . ? C11_2 C12_2 1.381(7) . ? C11_2 C16_2 1.427(7) . ? C12_2 C13_2 1.385(7) . ? C13_2 C14_2 1.400(8) . ? C14_2 C15_2 1.368(8) . ? C15_2 C16_2 1.396(7) . ? C16_2 C17_2 1.438(7) . ? C17_2 C18_2 1.499(7) . ? C18_2 C19_2 1.511(7) . ? C19_2 N20_2 1.483(6) . ? N20_2 C21_2 1.350(7) . ? C21_2 O21_2 1.244(6) . ? C21_2 C22_2 1.501(8) . ? C22_2 C23_2 1.518(8) . ? C24_2 C25_2 1.529(8) . ? C25_2 C26_2 1.519(9) . ? C26_2 C27_2 1.525(11) . ? C51 Cl1 1.683(8) . ? C51 Cl2 1.686(8) . ? C52 Cl3 1.685(9) . ? C52 Cl4 1.705(9) . ? 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 C2_1 S1_1 C5_1 91.6(5) . . ? C3_1 C2_1 S1_1 114.1(7) . . ? C4_1 C3_1 C2_1 111.3(10) . . ? C3_1 C4_1 C5_1 111.5(8) . . ? C4_1 C5_1 C6_1 130.4(5) . . ? C4_1 C5_1 S1_1 111.5(5) . . ? C6_1 C5_1 S1_1 118.2(5) . . ? O6_1 C6_1 C5_1 120.6(5) . . ? O6_1 C6_1 C7_1 121.8(5) . . ? C5_1 C6_1 C7_1 117.5(5) . . ? C23_1 C7_1 C6_1 107.8(4) . . ? C23_1 C7_1 C8_1 111.1(4) . . ? C6_1 C7_1 C8_1 113.2(4) . . ? N20_1 C8_1 C9_1 107.5(4) . . ? N20_1 C8_1 C24_1 111.0(4) . . ? C9_1 C8_1 C24_1 111.9(4) . . ? N20_1 C8_1 C7_1 105.0(4) . . ? C9_1 C8_1 C7_1 108.8(4) . . ? C24_1 C8_1 C7_1 112.4(4) . . ? C17_1 C9_1 N10_1 109.7(4) . . ? C17_1 C9_1 C8_1 126.9(4) . . ? N10_1 C9_1 C8_1 123.4(4) . . ? C11_1 N10_1 C9_1 108.7(4) . . ? N10_1 C11_1 C12_1 130.5(5) . . ? N10_1 C11_1 C16_1 107.8(4) . . ? C12_1 C11_1 C16_1 121.7(4) . . ? C11_1 C12_1 C13_1 117.3(5) . . ? C14_1 C13_1 C12_1 122.4(6) . . ? C15_1 C14_1 C13_1 120.7(5) . . ? C14_1 C15_1 C16_1 119.4(6) . . ? C15_1 C16_1 C11_1 118.6(5) . . ? C15_1 C16_1 C17_1 134.7(5) . . ? C11_1 C16_1 C17_1 106.7(4) . . ? C9_1 C17_1 C16_1 107.1(4) . . ? C9_1 C17_1 C18_1 121.3(4) . . ? C16_1 C17_1 C18_1 131.1(4) . . ? C17_1 C18_1 C19_1 107.9(4) . . ? N20_1 C19_1 C18_1 110.9(4) . . ? C21_1 N20_1 C19_1 117.7(4) . . ? C21_1 N20_1 C8_1 123.0(4) . . ? C19_1 N20_1 C8_1 119.3(4) . . ? O21_1 C21_1 N20_1 121.7(5) . . ? O21_1 C21_1 C22_1 118.4(5) . . ? N20_1 C21_1 C22_1 119.8(5) . . ? C21_1 C22_1 C23_1 118.3(4) . . ? C7_1 C23_1 C22_1 111.6(4) . . ? C25_1 C24_1 C8_1 115.1(4) . . ? C24_1 C25_1 C26_1 113.6(5) . . ? C27_1 C26_1 C25_1 114.0(6) . . ? C2_2 S1_2 C5_2 91.8(5) . . ? C3_2 C2_2 S1_2 112.9(6) . . ? C2_2 C3_2 C4_2 110.9(10) . . ? C5_2 C4_2 C3_2 115.6(8) . . ? C4_2 C5_2 C6_2 130.7(6) . . ? C4_2 C5_2 S1_2 108.7(5) . . ? C6_2 C5_2 S1_2 120.5(6) . . ? O6_2 C6_2 C5_2 121.2(6) . . ? O6_2 C6_2 C7_2 120.6(6) . . ? C5_2 C6_2 C7_2 118.1(6) . . ? C6_2 C7_2 C23_2 109.9(4) . . ? C6_2 C7_2 C8_2 114.2(4) . . ? C23_2 C7_2 C8_2 110.9(4) . . ? N20_2 C8_2 C9_2 107.1(4) . . ? N20_2 C8_2 C24_2 111.6(4) . . ? C9_2 C8_2 C24_2 112.2(4) . . ? N20_2 C8_2 C7_2 105.4(4) . . ? C9_2 C8_2 C7_2 108.0(4) . . ? C24_2 C8_2 C7_2 112.2(4) . . ? C17_2 C9_2 N10_2 110.2(4) . . ? C17_2 C9_2 C8_2 126.1(4) . . ? N10_2 C9_2 C8_2 123.6(4) . . ? C9_2 N10_2 C11_2 108.9(4) . . ? C12_2 C11_2 N10_2 130.6(4) . . ? C12_2 C11_2 C16_2 122.1(4) . . ? N10_2 C11_2 C16_2 107.3(4) . . ? C11_2 C12_2 C13_2 117.7(5) . . ? C12_2 C13_2 C14_2 120.4(5) . . ? C15_2 C14_2 C13_2 122.5(5) . . ? C14_2 C15_2 C16_2 118.4(5) . . ? C15_2 C16_2 C11_2 118.9(5) . . ? C15_2 C16_2 C17_2 134.6(5) . . ? C11_2 C16_2 C17_2 106.4(4) . . ? C9_2 C17_2 C16_2 107.2(4) . . ? C9_2 C17_2 C18_2 122.1(4) . . ? C16_2 C17_2 C18_2 130.1(4) . . ? C17_2 C18_2 C19_2 107.0(4) . . ? N20_2 C19_2 C18_2 110.7(4) . . ? C21_2 N20_2 C19_2 118.4(4) . . ? C21_2 N20_2 C8_2 122.4(4) . . ? C19_2 N20_2 C8_2 119.2(4) . . ? O21_2 C21_2 N20_2 121.0(5) . . ? O21_2 C21_2 C22_2 118.4(5) . . ? N20_2 C21_2 C22_2 120.6(5) . . ? C21_2 C22_2 C23_2 118.6(5) . . ? C22_2 C23_2 C7_2 111.0(4) . . ? C8_2 C24_2 C25_2 115.2(4) . . ? C26_2 C25_2 C24_2 112.6(5) . . ? C25_2 C26_2 C27_2 112.2(6) . . ? Cl1 C51 Cl2 116.7(6) . . ? Cl3 C52 Cl4 116.5(6) . . ? _diffrn_measured_fraction_theta_max 0.999 _diffrn_reflns_theta_full 21.96 _diffrn_measured_fraction_theta_full 0.999 _refine_diff_density_max 0.593 _refine_diff_density_min -0.488 _refine_diff_density_rms 0.060 #===================================================================== data_aka7 _database_code_depnum_ccdc_archive 'CCDC 281673' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common '6b in paper' _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C26 H27 N3 O4' _chemical_formula_weight 445.51 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)/c loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y-1/2, z-1/2' _cell_length_a 11.76200(10) _cell_length_b 13.00690(10) _cell_length_c 14.7316(2) _cell_angle_alpha 90.00 _cell_angle_beta 97.7240(10) _cell_angle_gamma 90.00 _cell_volume 2233.30(4) _cell_formula_units_Z 4 _cell_measurement_temperature 200(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description polyhedron _exptl_crystal_colour yellow _exptl_crystal_size_max 0.40 _exptl_crystal_size_mid 0.34 _exptl_crystal_size_min 0.11 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.325 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 944 _exptl_absorpt_coefficient_mu 0.090 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.9647 _exptl_absorpt_correction_T_max 0.9901 _exptl_absorpt_process_details 'Blessing, Acta Cryst. (1995) A51 33-38.' _exptl_special_details ; ? ; _diffrn_ambient_temperature 200(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'CCD area detector' _diffrn_measurement_method 'phi and omega scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 22678 _diffrn_reflns_av_R_equivalents 0.0294 _diffrn_reflns_av_sigmaI/netI 0.0252 _diffrn_reflns_limit_h_min -14 _diffrn_reflns_limit_h_max 15 _diffrn_reflns_limit_k_min -16 _diffrn_reflns_limit_k_max 16 _diffrn_reflns_limit_l_min -19 _diffrn_reflns_limit_l_max 19 _diffrn_reflns_theta_min 2.10 _diffrn_reflns_theta_max 27.46 _reflns_number_total 5107 _reflns_number_gt 3941 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'Bruker SMART' _computing_data_reduction 'Bruker SHELXTL' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Bruker SHELXTL' _computing_publication_material 'Bruker SHELXTL' _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0510P)^2^+0.7472P] 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_extinction_coef ? _refine_ls_number_reflns 5107 _refine_ls_number_parameters 298 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0583 _refine_ls_R_factor_gt 0.0413 _refine_ls_wR_factor_ref 0.1098 _refine_ls_wR_factor_gt 0.0999 _refine_ls_goodness_of_fit_ref 1.032 _refine_ls_restrained_S_all 1.032 _refine_ls_shift/su_max 0.001 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group C1 C 0.93126(11) 0.69090(10) 0.16787(8) 0.0211(3) Uani 1 1 d . . . C2 C 1.05295(11) 0.66871(10) 0.21293(8) 0.0222(3) Uani 1 1 d . . . N3 N 1.08844(9) 0.66675(9) 0.30635(7) 0.0248(2) Uani 1 1 d . . . H3 H 1.0457 0.6818 0.3492 0.030 Uiso 1 1 calc R . . C4 C 1.20211(11) 0.63721(10) 0.32114(9) 0.0255(3) Uani 1 1 d . . . C5 C 1.27400(13) 0.62085(12) 0.40335(10) 0.0326(3) Uani 1 1 d . . . H5 H 1.2482 0.6329 0.4608 0.039 Uiso 1 1 calc R . . C6 C 1.38371(13) 0.58650(13) 0.39786(11) 0.0393(4) Uani 1 1 d . . . H6 H 1.4342 0.5736 0.4526 0.047 Uiso 1 1 calc R . . C7 C 1.42244(13) 0.57009(12) 0.31283(12) 0.0382(4) Uani 1 1 d . . . H7 H 1.4984 0.5461 0.3114 0.046 Uiso 1 1 calc R . . C8 C 1.35265(12) 0.58807(11) 0.23160(11) 0.0318(3) Uani 1 1 d . . . H8 H 1.3803 0.5781 0.1746 0.038 Uiso 1 1 calc R . . C9 C 1.23962(11) 0.62150(10) 0.23486(9) 0.0256(3) Uani 1 1 d . . . C10 C 1.14289(11) 0.64261(10) 0.16700(9) 0.0248(3) Uani 1 1 d . . . C11 C 1.13366(12) 0.63859(11) 0.06441(9) 0.0285(3) Uani 1 1 d . . . H11A H 1.1701 0.5749 0.0454 0.034 Uiso 1 1 calc R . . H11B H 1.1741 0.6981 0.0418 0.034 Uiso 1 1 calc R . . C12 C 1.00731(12) 0.64075(11) 0.02344(9) 0.0266(3) Uani 1 1 d . . . H12A H 1.0007 0.6577 -0.0426 0.032 Uiso 1 1 calc R . . H12B H 0.9729 0.5721 0.0296 0.032 Uiso 1 1 calc R . . N13 N 0.94476(9) 0.71807(8) 0.07089(7) 0.0232(2) Uani 1 1 d . . . C14 C 0.94004(11) 0.81431(11) 0.03536(9) 0.0260(3) Uani 1 1 d . . . O14 O 0.96269(10) 0.83076(9) -0.04294(7) 0.0391(3) Uani 1 1 d . . . C15 C 0.90664(13) 0.90299(11) 0.09196(10) 0.0301(3) Uani 1 1 d . . . H15A H 0.8239 0.9173 0.0749 0.036 Uiso 1 1 calc R . . H15B H 0.9496 0.9649 0.0773 0.036 Uiso 1 1 calc R . . C16 C 0.92999(12) 0.88325(10) 0.19452(9) 0.0280(3) Uani 1 1 d . . . H16A H 0.8963 0.9393 0.2278 0.034 Uiso 1 1 calc R . . H16B H 1.0138 0.8823 0.2144 0.034 Uiso 1 1 calc R . . C17 C 0.87776(11) 0.78016(10) 0.21745(8) 0.0220(3) Uani 1 1 d . . . H17 H 0.8973 0.7688 0.2849 0.026 Uiso 1 1 calc R . . C18 C 0.74733(11) 0.78768(10) 0.19622(9) 0.0240(3) Uani 1 1 d . . . O18 O 0.69813(9) 0.77702(9) 0.11891(6) 0.0348(3) Uani 1 1 d . . . C19 C 0.67995(11) 0.81176(10) 0.27363(9) 0.0241(3) Uani 1 1 d . . . C20 C 0.73147(13) 0.84948(14) 0.35772(10) 0.0372(4) Uani 1 1 d . . . H20 H 0.8120 0.8609 0.3675 0.045 Uiso 1 1 calc R . . C21 C 0.66638(14) 0.87056(14) 0.42723(10) 0.0405(4) Uani 1 1 d . . . H21 H 0.7010 0.8972 0.4844 0.049 Uiso 1 1 calc R . . C22 C 0.56234(12) 0.79563(11) 0.25937(11) 0.0326(3) Uani 1 1 d . . . H22 H 0.5267 0.7714 0.2016 0.039 Uiso 1 1 calc R . . C23 C 0.49637(13) 0.81463(12) 0.32900(12) 0.0392(4) Uani 1 1 d . . . H23 H 0.4160 0.8023 0.3201 0.047 Uiso 1 1 calc R . . C24 C 0.55036(13) 0.85185(11) 0.41134(11) 0.0347(3) Uani 1 1 d . . . N25 N 0.48164(14) 0.87282(11) 0.48628(12) 0.0508(4) Uani 1 1 d . . . O26 O 0.37796(14) 0.85941(14) 0.47021(13) 0.0909(6) Uani 1 1 d . . . O27 O 0.53207(13) 0.90553(11) 0.55948(9) 0.0599(4) Uani 1 1 d . . . C28 C 0.85589(12) 0.59284(10) 0.16825(9) 0.0262(3) Uani 1 1 d . . . H28A H 0.7832 0.6047 0.1273 0.031 Uiso 1 1 calc R . . H28B H 0.8961 0.5353 0.1422 0.031 Uiso 1 1 calc R . . C29 C 0.82701(12) 0.56010(11) 0.26213(9) 0.0274(3) Uani 1 1 d . . . H29A H 0.8991 0.5465 0.3034 0.033 Uiso 1 1 calc R . . H29B H 0.7865 0.6170 0.2889 0.033 Uiso 1 1 calc R . . C30 C 0.75210(14) 0.46412(13) 0.25626(11) 0.0383(4) Uani 1 1 d . . . H30A H 0.6763 0.4803 0.2214 0.046 Uiso 1 1 calc R . . H30B H 0.7881 0.4099 0.2226 0.046 Uiso 1 1 calc R . . C31 C 0.73525(16) 0.42373(16) 0.35058(12) 0.0504(5) Uani 1 1 d . . . H31A H 0.6872 0.3620 0.3438 0.060 Uiso 1 1 calc R . . H31B H 0.6978 0.4765 0.3836 0.060 Uiso 1 1 calc R . . H31C H 0.8100 0.4067 0.3851 0.060 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 C1 0.0237(6) 0.0243(6) 0.0168(6) 0.0005(5) 0.0079(5) 0.0010(5) C2 0.0252(6) 0.0229(6) 0.0198(6) 0.0005(5) 0.0076(5) 0.0002(5) N3 0.0241(6) 0.0321(6) 0.0197(5) 0.0012(4) 0.0082(4) 0.0024(5) C4 0.0251(7) 0.0248(7) 0.0275(7) 0.0021(5) 0.0067(5) -0.0015(5) C5 0.0331(8) 0.0358(8) 0.0289(7) 0.0055(6) 0.0042(6) -0.0013(6) C6 0.0319(8) 0.0418(9) 0.0419(9) 0.0075(7) -0.0033(7) 0.0016(7) C7 0.0240(7) 0.0358(8) 0.0547(10) 0.0004(7) 0.0050(7) 0.0040(6) C8 0.0250(7) 0.0310(7) 0.0413(8) -0.0029(6) 0.0114(6) -0.0003(6) C9 0.0257(7) 0.0238(6) 0.0288(7) 0.0003(5) 0.0089(5) -0.0018(5) C10 0.0256(7) 0.0258(7) 0.0246(7) -0.0007(5) 0.0097(5) 0.0004(5) C11 0.0294(7) 0.0336(7) 0.0251(7) -0.0027(5) 0.0130(6) 0.0039(6) C12 0.0327(7) 0.0292(7) 0.0198(6) -0.0051(5) 0.0104(5) 0.0033(6) N13 0.0273(6) 0.0265(6) 0.0175(5) -0.0010(4) 0.0092(4) 0.0033(4) C14 0.0248(7) 0.0316(7) 0.0232(7) 0.0033(5) 0.0088(5) 0.0022(5) O14 0.0509(7) 0.0433(6) 0.0271(5) 0.0092(4) 0.0204(5) 0.0079(5) C15 0.0356(8) 0.0251(7) 0.0322(7) 0.0033(6) 0.0142(6) 0.0024(6) C16 0.0304(7) 0.0256(7) 0.0298(7) -0.0053(5) 0.0101(6) -0.0003(5) C17 0.0227(6) 0.0270(7) 0.0177(6) -0.0017(5) 0.0073(5) 0.0022(5) C18 0.0250(7) 0.0269(7) 0.0212(6) -0.0002(5) 0.0067(5) 0.0015(5) O18 0.0308(5) 0.0513(7) 0.0224(5) -0.0040(4) 0.0034(4) 0.0026(5) C19 0.0251(7) 0.0253(7) 0.0235(6) 0.0022(5) 0.0088(5) 0.0046(5) C20 0.0267(7) 0.0601(10) 0.0255(7) -0.0047(7) 0.0060(6) 0.0087(7) C21 0.0408(9) 0.0587(10) 0.0231(7) -0.0022(7) 0.0088(6) 0.0142(8) C22 0.0281(7) 0.0334(8) 0.0381(8) -0.0064(6) 0.0107(6) -0.0013(6) C23 0.0297(8) 0.0346(8) 0.0575(10) -0.0071(7) 0.0215(7) -0.0023(6) C24 0.0424(9) 0.0296(7) 0.0377(8) 0.0040(6) 0.0264(7) 0.0079(6) N25 0.0611(10) 0.0398(8) 0.0614(10) -0.0015(7) 0.0447(8) 0.0031(7) O26 0.0691(10) 0.1019(13) 0.1181(14) -0.0467(11) 0.0725(10) -0.0306(9) O27 0.0810(10) 0.0692(9) 0.0361(7) 0.0026(6) 0.0327(7) 0.0235(8) C28 0.0290(7) 0.0267(7) 0.0241(7) -0.0017(5) 0.0072(5) -0.0024(5) C29 0.0275(7) 0.0293(7) 0.0261(7) 0.0051(5) 0.0066(5) 0.0007(5) C30 0.0324(8) 0.0424(9) 0.0399(9) 0.0121(7) 0.0042(6) -0.0082(7) C31 0.0416(9) 0.0599(11) 0.0505(10) 0.0256(9) 0.0090(8) -0.0079(8) _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 N13 1.5008(15) . ? C1 C2 1.5222(18) . ? C1 C17 1.5495(17) . ? C1 C28 1.5537(18) . ? C2 C10 1.3728(18) . ? C2 N3 1.3836(16) . ? N3 C4 1.3800(17) . ? C4 C5 1.397(2) . ? C4 C9 1.4152(18) . ? C5 C6 1.378(2) . ? C6 C7 1.406(2) . ? C7 C8 1.377(2) . ? C8 C9 1.4057(19) . ? C9 C10 1.437(2) . ? C10 C11 1.5014(18) . ? C11 C12 1.527(2) . ? C12 N13 1.4764(16) . ? N13 C14 1.3550(17) . ? C14 O14 1.2369(16) . ? C14 C15 1.5060(19) . ? C15 C16 1.5208(19) . ? C16 C17 1.5315(18) . ? C17 C18 1.5270(18) . ? C18 O18 1.2141(16) . ? C18 C19 1.5065(17) . ? C19 C22 1.3870(19) . ? C19 C20 1.393(2) . ? C20 C21 1.386(2) . ? C21 C24 1.375(2) . ? C22 C23 1.389(2) . ? C23 C24 1.379(2) . ? C24 N25 1.4787(18) . ? N25 O26 1.223(2) . ? N25 O27 1.234(2) . ? C28 C29 1.5284(18) . ? C29 C30 1.524(2) . ? C30 C31 1.523(2) . ? 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 N13 C1 C2 104.26(9) . . ? N13 C1 C17 111.95(10) . . ? C2 C1 C17 110.74(10) . . ? N13 C1 C28 109.28(10) . . ? C2 C1 C28 110.26(10) . . ? C17 C1 C28 110.20(10) . . ? C10 C2 N3 109.65(12) . . ? C10 C2 C1 125.00(11) . . ? N3 C2 C1 125.28(11) . . ? C4 N3 C2 108.58(10) . . ? N3 C4 C5 129.79(13) . . ? N3 C4 C9 108.10(11) . . ? C5 C4 C9 122.09(13) . . ? C6 C5 C4 117.45(14) . . ? C5 C6 C7 121.31(14) . . ? C8 C7 C6 121.46(14) . . ? C7 C8 C9 118.62(14) . . ? C8 C9 C4 119.06(13) . . ? C8 C9 C10 134.39(13) . . ? C4 C9 C10 106.51(11) . . ? C2 C10 C9 107.15(12) . . ? C2 C10 C11 123.27(12) . . ? C9 C10 C11 129.58(12) . . ? C10 C11 C12 109.39(11) . . ? N13 C12 C11 110.23(11) . . ? C14 N13 C12 116.33(10) . . ? C14 N13 C1 125.54(10) . . ? C12 N13 C1 114.42(10) . . ? O14 C14 N13 121.15(12) . . ? O14 C14 C15 119.26(12) . . ? N13 C14 C15 119.59(11) . . ? C14 C15 C16 113.27(11) . . ? C15 C16 C17 110.04(11) . . ? C18 C17 C16 108.69(11) . . ? C18 C17 C1 114.33(10) . . ? C16 C17 C1 110.59(10) . . ? O18 C18 C19 120.05(12) . . ? O18 C18 C17 121.59(11) . . ? C19 C18 C17 118.33(11) . . ? C22 C19 C20 119.59(12) . . ? C22 C19 C18 117.99(12) . . ? C20 C19 C18 122.42(12) . . ? C21 C20 C19 120.62(14) . . ? C24 C21 C20 118.25(15) . . ? C19 C22 C23 120.40(14) . . ? C24 C23 C22 118.37(14) . . ? C21 C24 C23 122.76(13) . . ? C21 C24 N25 118.02(15) . . ? C23 C24 N25 119.22(15) . . ? O26 N25 O27 124.60(15) . . ? O26 N25 C24 117.38(17) . . ? O27 N25 C24 117.98(15) . . ? C29 C28 C1 115.36(11) . . ? C30 C29 C28 111.97(12) . . ? C31 C30 C29 112.09(14) . . ? _diffrn_measured_fraction_theta_max 0.999 _diffrn_reflns_theta_full 27.46 _diffrn_measured_fraction_theta_full 0.999 _refine_diff_density_max 0.334 _refine_diff_density_min -0.270 _refine_diff_density_rms 0.039 #===================================================================== data_aka8 _database_code_depnum_ccdc_archive 'CCDC 281674' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common '6c in paper?' _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C27 H30 N2 O3' _chemical_formula_weight 430.53 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 C2/c 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 15.69130(10) _cell_length_b 16.5338(2) _cell_length_c 18.1420(2) _cell_angle_alpha 90.00 _cell_angle_beta 99.5740(10) _cell_angle_gamma 90.00 _cell_volume 4641.15(8) _cell_formula_units_Z 8 _cell_measurement_temperature 298(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description polyhedron _exptl_crystal_colour colorless _exptl_crystal_size_max 0.46 _exptl_crystal_size_mid 0.32 _exptl_crystal_size_min 0.30 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.232 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1840 _exptl_absorpt_coefficient_mu 0.080 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.9640 _exptl_absorpt_correction_T_max 0.9763 _exptl_absorpt_process_details 'Blessing, Acta Cryst. (1995) A51 33-38.' _exptl_special_details ; ? ; _diffrn_ambient_temperature 298(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'CCD area detector' _diffrn_measurement_method 'phi and omega scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 23712 _diffrn_reflns_av_R_equivalents 0.0371 _diffrn_reflns_av_sigmaI/netI 0.0344 _diffrn_reflns_limit_h_min -20 _diffrn_reflns_limit_h_max 20 _diffrn_reflns_limit_k_min -21 _diffrn_reflns_limit_k_max 21 _diffrn_reflns_limit_l_min -23 _diffrn_reflns_limit_l_max 23 _diffrn_reflns_theta_min 1.80 _diffrn_reflns_theta_max 27.47 _reflns_number_total 5323 _reflns_number_gt 2835 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'Bruker SMART' _computing_data_reduction 'Bruker SHELXTL' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Bruker SHELXTL' _computing_publication_material 'Bruker SHELXTL' _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0717P)^2^+0.6652P] 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 0.0039(4) _refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^ _refine_ls_number_reflns 5323 _refine_ls_number_parameters 300 _refine_ls_number_restraints 2 _refine_ls_R_factor_all 0.1037 _refine_ls_R_factor_gt 0.0495 _refine_ls_wR_factor_ref 0.1477 _refine_ls_wR_factor_gt 0.1203 _refine_ls_goodness_of_fit_ref 1.007 _refine_ls_restrained_S_all 1.009 _refine_ls_shift/su_max 0.000 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group C1 C 0.32810(9) 0.26095(11) 0.82967(8) 0.0565(4) Uani 1 1 d . . . C2 C 0.28090(10) 0.20656(10) 0.77023(9) 0.0556(4) Uani 1 1 d . . . N3 N 0.32231(10) 0.16377(9) 0.72081(7) 0.0595(4) Uani 1 1 d . . . H3 H 0.3769(12) 0.1662(10) 0.7148(10) 0.069(5) Uiso 1 1 d . . . C4 C 0.26146(11) 0.11982(11) 0.67407(9) 0.0600(4) Uani 1 1 d . . . C5 C 0.27081(14) 0.06935(11) 0.61495(10) 0.0729(5) Uani 1 1 d . . . H5 H 0.3249 0.0590 0.6025 0.087 Uiso 1 1 calc R . . C6 C 0.19717(16) 0.03519(13) 0.57543(11) 0.0861(6) Uani 1 1 d . . . H6 H 0.2015 0.0014 0.5352 0.103 Uiso 1 1 calc R . . C7 C 0.11668(16) 0.05001(14) 0.59432(13) 0.0908(7) Uani 1 1 d . . . H7 H 0.0680 0.0266 0.5661 0.109 Uiso 1 1 calc R . . C8 C 0.10701(13) 0.09844(13) 0.65380(12) 0.0819(6) Uani 1 1 d . . . H8 H 0.0527 0.1070 0.6664 0.098 Uiso 1 1 calc R . . C9 C 0.18045(11) 0.13471(11) 0.69511(10) 0.0633(5) Uani 1 1 d . . . C10 C 0.19506(10) 0.19004(11) 0.75644(9) 0.0623(5) Uani 1 1 d . . . C11 C 0.13299(11) 0.23121(14) 0.79824(12) 0.0834(6) Uani 1 1 d . . . H11A H 0.1218 0.1974 0.8392 0.100 Uiso 1 1 calc R . . H11B H 0.0787 0.2410 0.7653 0.100 Uiso 1 1 calc R . . C12 C 0.17268(12) 0.31045(14) 0.82797(12) 0.0832(6) Uani 1 1 d . . . H12A H 0.1731 0.3476 0.7867 0.100 Uiso 1 1 calc R . . H12B H 0.1375 0.3341 0.8615 0.100 Uiso 1 1 calc R . . N13 N 0.26135(8) 0.29994(9) 0.86800(8) 0.0624(4) Uani 1 1 d . . . O14 O 0.22412(9) 0.35658(8) 0.97160(7) 0.0856(4) Uani 1 1 d . . . C14 C 0.27974(12) 0.32678(10) 0.93954(10) 0.0647(5) Uani 1 1 d . . . C15 C 0.37036(14) 0.32167(13) 0.97993(11) 0.0817(6) Uani 1 1 d . . . H15A H 0.3681 0.3106 1.0321 0.098 Uiso 1 1 calc R . . H15B H 0.3964 0.3746 0.9778 0.098 Uiso 1 1 calc R . . C16 C 0.43059(12) 0.26019(13) 0.95378(10) 0.0767(6) Uani 1 1 d . . . H16A H 0.4554 0.2262 0.9955 0.092 Uiso 1 1 calc R . . H16B H 0.4774 0.2881 0.9357 0.092 Uiso 1 1 calc R . . C17 C 0.38216(10) 0.20788(11) 0.89185(9) 0.0609(5) Uani 1 1 d . . . H17 H 0.3407 0.1758 0.9143 0.073 Uiso 1 1 calc R . . O18 O 0.50402(8) 0.17294(10) 0.83509(8) 0.0915(5) Uani 1 1 d . . . C18 C 0.44469(10) 0.14800(13) 0.86538(9) 0.0669(5) Uani 1 1 d . . . C19 C 0.43446(11) 0.06066(12) 0.87960(9) 0.0661(5) Uani 1 1 d . . . C20 C 0.38001(14) 0.03028(14) 0.92530(11) 0.0852(6) Uani 1 1 d . . . H20 H 0.3485 0.0662 0.9496 0.102 Uiso 1 1 calc R . . C21 C 0.37085(15) -0.05135(14) 0.93605(12) 0.0914(7) Uani 1 1 d . . . H21 H 0.3345 -0.0696 0.9681 0.110 Uiso 1 1 calc R . . C22 C 0.48115(12) 0.00442(16) 0.84534(12) 0.0880(7) Uani 1 1 d . . . H22 H 0.5203 0.0225 0.8158 0.106 Uiso 1 1 calc R . . C23 C 0.47050(14) -0.07714(17) 0.85436(14) 0.0979(8) Uani 1 1 d . . . H23 H 0.5010 -0.1135 0.8296 0.117 Uiso 1 1 calc R . . C24 C 0.41485(13) -0.10583(14) 0.89994(11) 0.0786(6) Uani 1 1 d . . . O25 O 0.40829(10) -0.18788(10) 0.90488(9) 0.1013(5) Uani 1 1 d . . . C26 C 0.35004(17) -0.21958(15) 0.94993(15) 0.1064(8) Uani 1 1 d . . . H26A H 0.3647 -0.1988 0.9998 0.160 Uiso 1 1 calc R . . H26B H 0.3540 -0.2775 0.9510 0.160 Uiso 1 1 calc R . . H26C H 0.2921 -0.2038 0.9293 0.160 Uiso 1 1 calc R . . C28 C 0.38085(11) 0.32512(11) 0.79509(9) 0.0663(5) Uani 1 1 d . . . H28A H 0.4120 0.3577 0.8352 0.080 Uiso 1 1 calc R . . H28B H 0.4234 0.2975 0.7711 0.080 Uiso 1 1 calc R . . C29 C 0.32939(15) 0.38122(14) 0.73851(11) 0.0924(7) Uani 1 1 d D A . H29A H 0.2917 0.3490 0.7020 0.111 Uiso 1 1 calc R . . H29B H 0.2931 0.4152 0.7639 0.111 Uiso 1 1 calc R . . C30 C 0.3844(2) 0.43456(18) 0.69804(15) 0.1290(10) Uani 1 1 d D . . H30A H 0.4194 0.4671 0.7360 0.155 Uiso 0.622(5) 1 calc PR A 1 H30B H 0.4240 0.3989 0.6779 0.155 Uiso 0.622(5) 1 calc PR A 1 H30C H 0.3581 0.4876 0.6895 0.155 Uiso 0.378(5) 1 calc PR A 2 H30D H 0.4413 0.4411 0.7279 0.155 Uiso 0.378(5) 1 calc PR A 2 C31 C 0.3522(3) 0.4859(3) 0.6421(2) 0.131(2) Uani 0.622(5) 1 d PD A 1 H31A H 0.3990 0.5132 0.6246 0.197 Uiso 0.622(5) 1 calc PR A 1 H31B H 0.3155 0.5249 0.6604 0.197 Uiso 0.622(5) 1 calc PR A 1 H31C H 0.3194 0.4558 0.6018 0.197 Uiso 0.622(5) 1 calc PR A 1 C31B C 0.3913(4) 0.3987(4) 0.6308(4) 0.103(3) Uiso 0.378(5) 1 d PD A 2 H31D H 0.4284 0.4306 0.6053 0.155 Uiso 0.378(5) 1 calc PR A 2 H31E H 0.3351 0.3950 0.6006 0.155 Uiso 0.378(5) 1 calc PR A 2 H31F H 0.4152 0.3454 0.6396 0.155 Uiso 0.378(5) 1 calc PR A 2 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 0.0437(9) 0.0784(11) 0.0504(9) -0.0033(8) 0.0162(7) 0.0048(8) C2 0.0457(9) 0.0746(11) 0.0498(9) -0.0017(8) 0.0174(7) 0.0035(8) N3 0.0471(8) 0.0798(10) 0.0556(8) -0.0071(7) 0.0198(7) 0.0012(7) C4 0.0621(10) 0.0674(11) 0.0516(9) 0.0018(9) 0.0130(8) 0.0009(9) C5 0.0837(14) 0.0735(12) 0.0636(11) -0.0040(10) 0.0187(10) 0.0038(10) C6 0.1127(19) 0.0756(13) 0.0691(13) -0.0105(10) 0.0127(13) -0.0086(12) C7 0.0964(17) 0.0866(15) 0.0839(15) -0.0100(12) -0.0014(13) -0.0254(13) C8 0.0676(12) 0.0954(15) 0.0810(13) -0.0023(12) 0.0071(11) -0.0162(11) C9 0.0558(10) 0.0746(12) 0.0603(10) 0.0027(9) 0.0119(8) -0.0043(9) C10 0.0450(9) 0.0851(12) 0.0592(10) -0.0022(9) 0.0158(8) 0.0000(8) C11 0.0450(10) 0.1265(18) 0.0814(13) -0.0145(13) 0.0189(9) 0.0044(11) C12 0.0544(11) 0.1117(16) 0.0852(13) -0.0174(12) 0.0164(10) 0.0235(11) N13 0.0518(8) 0.0797(10) 0.0591(9) -0.0072(7) 0.0194(7) 0.0086(7) O14 0.1005(10) 0.0856(9) 0.0826(9) -0.0118(7) 0.0498(8) 0.0092(7) C14 0.0756(12) 0.0643(11) 0.0607(11) -0.0010(9) 0.0306(10) 0.0002(9) C15 0.0938(15) 0.0876(14) 0.0628(11) -0.0098(11) 0.0109(11) 0.0007(11) C16 0.0690(12) 0.1061(16) 0.0546(10) 0.0017(10) 0.0092(9) 0.0010(11) C17 0.0495(9) 0.0827(12) 0.0538(9) 0.0021(9) 0.0185(8) 0.0055(8) O18 0.0578(8) 0.1285(12) 0.0971(10) 0.0077(9) 0.0387(8) 0.0139(7) C18 0.0425(9) 0.1063(16) 0.0537(10) -0.0011(10) 0.0131(8) 0.0128(9) C19 0.0486(10) 0.0956(15) 0.0552(10) -0.0044(9) 0.0121(8) 0.0221(9) C20 0.0963(15) 0.0884(16) 0.0808(13) -0.0027(11) 0.0436(12) 0.0284(12) C21 0.1105(17) 0.0885(16) 0.0840(14) 0.0044(12) 0.0418(13) 0.0307(13) C22 0.0600(12) 0.1160(19) 0.0931(15) -0.0124(13) 0.0281(11) 0.0228(12) C23 0.0719(14) 0.115(2) 0.1083(18) -0.0277(15) 0.0194(13) 0.0378(13) C24 0.0720(13) 0.0900(16) 0.0698(12) -0.0096(11) 0.0000(10) 0.0306(11) O25 0.1047(12) 0.0900(12) 0.1053(12) -0.0151(9) 0.0060(10) 0.0352(9) C26 0.1133(19) 0.0937(17) 0.1070(18) -0.0027(14) 0.0027(16) 0.0185(15) C28 0.0598(10) 0.0863(13) 0.0553(10) -0.0045(9) 0.0166(8) -0.0072(9) C29 0.1025(16) 0.1016(16) 0.0698(12) 0.0116(12) 0.0047(12) -0.0145(13) C30 0.176(3) 0.124(2) 0.0885(17) 0.0189(17) 0.0273(18) -0.035(2) C31 0.146(4) 0.137(4) 0.104(3) 0.047(3) -0.003(3) -0.026(3) _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 N13 1.4961(19) . ? C1 C2 1.502(2) . ? C1 C28 1.542(2) . ? C1 C17 1.563(2) . ? C2 C10 1.356(2) . ? C2 N3 1.386(2) . ? N3 C4 1.375(2) . ? C4 C5 1.386(2) . ? C4 C9 1.408(2) . ? C5 C6 1.376(3) . ? C6 C7 1.384(3) . ? C7 C8 1.372(3) . ? C8 C9 1.401(3) . ? C9 C10 1.429(2) . ? C10 C11 1.494(2) . ? C11 C12 1.511(3) . ? C12 N13 1.469(2) . ? N13 C14 1.357(2) . ? O14 C14 1.2295(19) . ? C14 C15 1.490(3) . ? C15 C16 1.517(3) . ? C16 C17 1.518(2) . ? C17 C18 1.527(2) . ? O18 C18 1.228(2) . ? C18 C19 1.480(3) . ? C19 C20 1.380(3) . ? C19 C22 1.393(2) . ? C20 C21 1.375(3) . ? C21 C24 1.367(3) . ? C22 C23 1.372(3) . ? C23 C24 1.382(3) . ? C24 O25 1.365(3) . ? O25 C26 1.424(3) . ? C28 C29 1.513(3) . ? C29 C30 1.508(3) . ? C30 C31 1.354(4) . ? C30 C31B 1.377(6) . ? 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 N13 C1 C2 106.98(12) . . ? N13 C1 C28 110.93(14) . . ? C2 C1 C28 110.73(13) . . ? N13 C1 C17 104.15(12) . . ? C2 C1 C17 109.01(14) . . ? C28 C1 C17 114.60(13) . . ? C10 C2 N3 109.64(15) . . ? C10 C2 C1 127.53(14) . . ? N3 C2 C1 122.83(13) . . ? C4 N3 C2 108.46(14) . . ? N3 C4 C5 130.06(16) . . ? N3 C4 C9 107.82(15) . . ? C5 C4 C9 122.11(17) . . ? C6 C5 C4 117.56(19) . . ? C5 C6 C7 121.3(2) . . ? C8 C7 C6 121.5(2) . . ? C7 C8 C9 118.8(2) . . ? C8 C9 C4 118.65(17) . . ? C8 C9 C10 134.57(17) . . ? C4 C9 C10 106.72(15) . . ? C2 C10 C9 107.35(14) . . ? C2 C10 C11 121.73(16) . . ? C9 C10 C11 130.77(15) . . ? C10 C11 C12 108.14(15) . . ? N13 C12 C11 111.98(16) . . ? C14 N13 C12 117.88(14) . . ? C14 N13 C1 122.11(14) . . ? C12 N13 C1 120.01(13) . . ? O14 C14 N13 121.93(18) . . ? O14 C14 C15 118.99(17) . . ? N13 C14 C15 119.07(15) . . ? C14 C15 C16 118.52(16) . . ? C15 C16 C17 110.61(15) . . ? C16 C17 C18 109.48(14) . . ? C16 C17 C1 111.04(15) . . ? C18 C17 C1 115.92(13) . . ? O18 C18 C19 121.18(16) . . ? O18 C18 C17 119.84(19) . . ? C19 C18 C17 118.94(15) . . ? C20 C19 C22 116.7(2) . . ? C20 C19 C18 123.75(16) . . ? C22 C19 C18 119.55(18) . . ? C21 C20 C19 122.15(18) . . ? C24 C21 C20 120.4(2) . . ? C23 C22 C19 121.3(2) . . ? C22 C23 C24 120.7(2) . . ? O25 C24 C21 125.0(2) . . ? O25 C24 C23 116.26(19) . . ? C21 C24 C23 118.7(2) . . ? C24 O25 C26 117.80(17) . . ? C29 C28 C1 115.84(15) . . ? C30 C29 C28 113.9(2) . . ? C31 C30 C31B 71.4(4) . . ? C31 C30 C29 124.0(3) . . ? C31B C30 C29 108.4(4) . . ? _diffrn_measured_fraction_theta_max 0.999 _diffrn_reflns_theta_full 27.47 _diffrn_measured_fraction_theta_full 0.999 _refine_diff_density_max 0.218 _refine_diff_density_min -0.178 _refine_diff_density_rms 0.050 #===================================================================== data_aka9 _database_code_depnum_ccdc_archive 'CCDC 281675' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common '6e in paper' _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C25 H26 N2 O2 S' _chemical_formula_weight 418.54 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' S S 0.1246 0.1234 '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)/n loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, y+1/2, -z+1/2' '-x, -y, -z' 'x-1/2, -y-1/2, z-1/2' _cell_length_a 9.8924(2) _cell_length_b 10.3918(2) _cell_length_c 23.1132(4) _cell_angle_alpha 90.00 _cell_angle_beta 95.4720(10) _cell_angle_gamma 90.00 _cell_volume 2365.21(8) _cell_formula_units_Z 4 _cell_measurement_temperature 200(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description polyhedron _exptl_crystal_colour colorless _exptl_crystal_size_max 0.40 _exptl_crystal_size_mid 0.28 _exptl_crystal_size_min 0.08 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.175 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 888 _exptl_absorpt_coefficient_mu 0.159 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.9391 _exptl_absorpt_correction_T_max 0.9874 _exptl_absorpt_process_details 'Blessing, Acta Cryst. (1995) A51 33-38.' _exptl_special_details ; ? ; _diffrn_ambient_temperature 200(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'CCD area detector' _diffrn_measurement_method 'phi and omega scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 23864 _diffrn_reflns_av_R_equivalents 0.0363 _diffrn_reflns_av_sigmaI/netI 0.0317 _diffrn_reflns_limit_h_min -12 _diffrn_reflns_limit_h_max 12 _diffrn_reflns_limit_k_min -13 _diffrn_reflns_limit_k_max 13 _diffrn_reflns_limit_l_min -29 _diffrn_reflns_limit_l_max 29 _diffrn_reflns_theta_min 1.77 _diffrn_reflns_theta_max 27.45 _reflns_number_total 5407 _reflns_number_gt 3937 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'Bruker SMART' _computing_data_reduction 'Bruker SHELXTL' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Bruker SHELXTL' _computing_publication_material 'Bruker SHELXTL' _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0543P)^2^+0.7675P] 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_number_reflns 5407 _refine_ls_number_parameters 300 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0653 _refine_ls_R_factor_gt 0.0414 _refine_ls_wR_factor_ref 0.1147 _refine_ls_wR_factor_gt 0.1027 _refine_ls_goodness_of_fit_ref 1.028 _refine_ls_restrained_S_all 1.028 _refine_ls_shift/su_max 0.005 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group S1 S 0.07969(5) 0.21267(5) 0.13304(2) 0.04832(15) Uani 1 1 d . . . C1 C -0.37530(14) -0.01449(15) 0.16639(6) 0.0248(3) Uani 1 1 d . . . C2 C -0.44848(15) -0.14033(15) 0.15107(6) 0.0256(3) Uani 1 1 d . . . N3 N -0.40304(13) -0.23574(13) 0.11618(6) 0.0264(3) Uani 1 1 d . . . H3 H -0.326(2) -0.2450(18) 0.1034(8) 0.039(5) Uiso 1 1 d . . . C4 C -0.49885(16) -0.33270(15) 0.11071(7) 0.0293(3) Uani 1 1 d . . . C5 C -0.49700(19) -0.44909(16) 0.08096(8) 0.0395(4) Uani 1 1 d . . . H5 H -0.4221 -0.4732 0.0605 0.047 Uiso 1 1 calc R . . C6 C -0.6093(2) -0.52807(19) 0.08253(9) 0.0507(5) Uani 1 1 d . . . H6 H -0.6113 -0.6084 0.0628 0.061 Uiso 1 1 calc R . . C7 C -0.7195(2) -0.4924(2) 0.11235(9) 0.0527(5) Uani 1 1 d . . . H7 H -0.7951 -0.5487 0.1122 0.063 Uiso 1 1 calc R . . C8 C -0.72125(19) -0.3772(2) 0.14207(8) 0.0442(5) Uani 1 1 d . . . H8 H -0.7970 -0.3539 0.1622 0.053 Uiso 1 1 calc R . . C9 C -0.60854(16) -0.29526(17) 0.14187(7) 0.0330(4) Uani 1 1 d . . . C10 C -0.57405(16) -0.17195(17) 0.16745(7) 0.0323(4) Uani 1 1 d . . . C11 C -0.65056(17) -0.0908(2) 0.20660(8) 0.0423(4) Uani 1 1 d . . . H11A H -0.6479 -0.1314 0.2454 0.051 Uiso 1 1 calc R . . H11B H -0.7467 -0.0840 0.1905 0.051 Uiso 1 1 calc R . . C12 C -0.58768(16) 0.04289(19) 0.21219(8) 0.0382(4) Uani 1 1 d . . . H12A H -0.6166 0.0940 0.1770 0.046 Uiso 1 1 calc R . . H12B H -0.6195 0.0875 0.2462 0.046 Uiso 1 1 calc R . . N13 N -0.43790(13) 0.03278(14) 0.21926(5) 0.0297(3) Uani 1 1 d . . . C14 C -0.37792(17) 0.03171(17) 0.27412(7) 0.0338(4) Uani 1 1 d . . . O14 O -0.44256(13) 0.06492(15) 0.31524(5) 0.0495(4) Uani 1 1 d . . . C15 C -0.23277(17) -0.00915(18) 0.28541(7) 0.0358(4) Uani 1 1 d . . . H15A H -0.2210 -0.0546 0.3232 0.043 Uiso 1 1 calc R . . H15B H -0.1749 0.0688 0.2888 0.043 Uiso 1 1 calc R . . C16 C -0.18295(15) -0.09642(16) 0.23895(7) 0.0294(3) Uani 1 1 d . . . H16 H -0.2329 -0.1799 0.2402 0.035 Uiso 1 1 calc R . . C17 C -0.21948(14) -0.03658(14) 0.17845(6) 0.0233(3) Uani 1 1 d . . . H17 H -0.1928 -0.1000 0.1490 0.028 Uiso 1 1 calc R . . C18 C -0.13434(15) 0.08461(15) 0.17235(6) 0.0259(3) Uani 1 1 d . . . O18 O -0.15690(13) 0.18410(11) 0.19727(6) 0.0431(3) Uani 1 1 d . . . C19 C -0.01998(15) 0.07778(15) 0.13635(7) 0.0282(3) Uani 1 1 d . . . C20 C 0.02120(16) -0.02011(18) 0.10060(7) 0.0348(4) Uani 1 1 d . . . H20 H -0.0202 -0.1025 0.0964 0.042 Uiso 1 1 calc R . . C21 C 0.1339(2) 0.0206(2) 0.07125(9) 0.0551(6) Uani 1 1 d . . . H21 H 0.1762 -0.0321 0.0447 0.066 Uiso 1 1 calc R . . C22 C 0.1744(2) 0.1417(2) 0.08508(10) 0.0580(6) Uani 1 1 d . . . H22 H 0.2486 0.1828 0.0694 0.070 Uiso 1 1 calc R . . C23 C -0.03155(17) -0.12535(19) 0.25175(8) 0.0397(4) Uani 1 1 d . . . H23A H 0.0196 -0.0445 0.2539 0.060 Uiso 1 1 calc R . . H23B H -0.0012 -0.1792 0.2207 0.060 Uiso 1 1 calc R . . H23C H -0.0161 -0.1709 0.2889 0.060 Uiso 1 1 calc R . . C28 C -0.40629(16) 0.08596(16) 0.11722(7) 0.0295(3) Uani 1 1 d . . . H28A H -0.5058 0.0988 0.1115 0.035 Uiso 1 1 calc R . . H28B H -0.3651 0.1690 0.1305 0.035 Uiso 1 1 calc R . . C29 C -0.35636(16) 0.05281(15) 0.05840(6) 0.0286(3) Uani 1 1 d . . . H29A H -0.4091 -0.0210 0.0411 0.034 Uiso 1 1 calc R . . H29B H -0.2597 0.0269 0.0642 0.034 Uiso 1 1 calc R . . C30 C -0.37148(17) 0.16771(16) 0.01649(7) 0.0341(4) Uani 1 1 d . . . H30A H -0.3674 0.1362 -0.0237 0.041 Uiso 1 1 calc R . . H30B H -0.4618 0.2074 0.0188 0.041 Uiso 1 1 calc R . . C31 C -0.2625(2) 0.26966(19) 0.02953(9) 0.0495(5) Uani 1 1 d . . . H31A H -0.2668 0.3023 0.0691 0.074 Uiso 1 1 calc R . . H31B H -0.2777 0.3406 0.0017 0.074 Uiso 1 1 calc R . . H31C H -0.1729 0.2317 0.0262 0.074 Uiso 1 1 calc R . . C60 C -0.4143(2) 0.1258(2) 0.45854(8) 0.0582(6) Uani 1 1 d . . . H60A H -0.3987 0.0331 0.4554 0.087 Uiso 1 1 calc R . . H60B H -0.5121 0.1426 0.4569 0.087 Uiso 1 1 calc R . . H60C H -0.3699 0.1574 0.4955 0.087 Uiso 1 1 calc R . . O60 O -0.36007(13) 0.18966(13) 0.41235(6) 0.0442(3) Uani 1 1 d . . . H60 H -0.379(2) 0.150(2) 0.3810(11) 0.069(8) Uiso 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 S1 0.0372(3) 0.0440(3) 0.0646(3) 0.0098(2) 0.0094(2) -0.0145(2) C1 0.0224(7) 0.0323(8) 0.0206(7) -0.0036(6) 0.0065(6) -0.0017(6) C2 0.0228(7) 0.0336(8) 0.0206(7) 0.0013(6) 0.0028(5) -0.0037(6) N3 0.0228(7) 0.0301(7) 0.0263(6) 0.0001(5) 0.0017(5) -0.0037(5) C4 0.0291(8) 0.0296(8) 0.0277(8) 0.0077(6) -0.0049(6) -0.0065(6) C5 0.0423(10) 0.0307(9) 0.0437(10) 0.0028(8) -0.0054(8) -0.0039(7) C6 0.0550(12) 0.0329(10) 0.0611(13) 0.0040(9) -0.0099(10) -0.0135(9) C7 0.0514(12) 0.0452(12) 0.0587(13) 0.0152(10) -0.0096(10) -0.0263(10) C8 0.0356(9) 0.0565(12) 0.0398(10) 0.0141(9) 0.0002(8) -0.0170(9) C9 0.0300(8) 0.0419(10) 0.0262(8) 0.0095(7) -0.0017(6) -0.0105(7) C10 0.0253(8) 0.0454(10) 0.0264(8) 0.0027(7) 0.0033(6) -0.0085(7) C11 0.0264(8) 0.0675(13) 0.0345(9) -0.0056(9) 0.0101(7) -0.0087(8) C12 0.0249(8) 0.0583(12) 0.0327(9) -0.0092(8) 0.0095(7) 0.0014(8) N13 0.0240(7) 0.0418(8) 0.0244(6) -0.0064(6) 0.0078(5) -0.0010(6) C14 0.0345(9) 0.0416(10) 0.0264(8) -0.0055(7) 0.0090(7) -0.0079(7) O14 0.0436(7) 0.0783(10) 0.0284(6) -0.0135(6) 0.0132(5) -0.0028(7) C15 0.0349(9) 0.0494(10) 0.0229(8) 0.0000(7) 0.0012(7) -0.0058(8) C16 0.0278(8) 0.0321(8) 0.0282(8) 0.0040(6) 0.0019(6) -0.0058(6) C17 0.0212(7) 0.0254(7) 0.0239(7) -0.0021(6) 0.0050(6) -0.0031(6) C18 0.0253(7) 0.0267(8) 0.0260(7) -0.0002(6) 0.0034(6) -0.0012(6) O18 0.0473(7) 0.0288(6) 0.0561(8) -0.0123(6) 0.0203(6) -0.0061(5) C19 0.0218(7) 0.0315(8) 0.0314(8) 0.0039(7) 0.0026(6) -0.0051(6) C20 0.0268(8) 0.0434(10) 0.0357(9) -0.0007(7) 0.0103(7) -0.0012(7) C21 0.0424(11) 0.0762(16) 0.0504(12) 0.0025(11) 0.0234(9) 0.0075(11) C22 0.0316(10) 0.0780(16) 0.0669(14) 0.0238(12) 0.0174(9) -0.0092(10) C23 0.0339(9) 0.0444(10) 0.0395(10) 0.0076(8) -0.0030(7) 0.0023(8) C28 0.0270(8) 0.0321(8) 0.0298(8) 0.0014(7) 0.0052(6) 0.0048(6) C29 0.0298(8) 0.0316(8) 0.0242(7) 0.0006(6) 0.0015(6) 0.0012(6) C30 0.0344(9) 0.0385(9) 0.0292(8) 0.0075(7) 0.0028(7) 0.0047(7) C31 0.0579(12) 0.0418(11) 0.0481(11) 0.0140(9) 0.0013(9) -0.0087(9) C60 0.0655(14) 0.0740(15) 0.0358(10) 0.0024(10) 0.0090(10) -0.0117(12) O60 0.0467(8) 0.0486(8) 0.0388(7) -0.0090(6) 0.0122(6) -0.0148(6) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag S1 C22 1.688(2) . ? S1 C19 1.7197(16) . ? C1 N13 1.5043(18) . ? C1 C2 1.520(2) . ? C1 C28 1.552(2) . ? C1 C17 1.557(2) . ? C2 C10 1.373(2) . ? C2 N3 1.380(2) . ? N3 C4 1.3808(19) . ? C4 C5 1.392(2) . ? C4 C9 1.413(2) . ? C5 C6 1.384(3) . ? C6 C7 1.394(3) . ? C7 C8 1.381(3) . ? C8 C9 1.403(2) . ? C9 C10 1.439(2) . ? C10 C11 1.494(2) . ? C11 C12 1.523(3) . ? C12 N13 1.479(2) . ? N13 C14 1.348(2) . ? C14 O14 1.2440(19) . ? C14 C15 1.496(2) . ? C15 C16 1.523(2) . ? C16 C23 1.529(2) . ? C16 C17 1.542(2) . ? C17 C18 1.529(2) . ? C18 O18 1.2144(19) . ? C18 C19 1.469(2) . ? C19 C20 1.396(2) . ? C20 C21 1.423(2) . ? C21 C22 1.350(3) . ? C28 C29 1.529(2) . ? C29 C30 1.536(2) . ? C30 C31 1.521(3) . ? C60 O60 1.406(2) . ? 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 C22 S1 C19 91.69(10) . . ? N13 C1 C2 104.26(11) . . ? N13 C1 C28 107.90(12) . . ? C2 C1 C28 110.59(12) . . ? N13 C1 C17 112.33(12) . . ? C2 C1 C17 110.87(12) . . ? C28 C1 C17 110.69(12) . . ? C10 C2 N3 110.06(14) . . ? C10 C2 C1 124.41(14) . . ? N3 C2 C1 125.43(12) . . ? C2 N3 C4 108.59(13) . . ? N3 C4 C5 129.63(16) . . ? N3 C4 C9 107.83(14) . . ? C5 C4 C9 122.54(15) . . ? C6 C5 C4 116.98(18) . . ? C5 C6 C7 121.48(19) . . ? C8 C7 C6 121.61(17) . . ? C7 C8 C9 118.45(19) . . ? C8 C9 C4 118.93(17) . . ? C8 C9 C10 134.14(17) . . ? C4 C9 C10 106.93(13) . . ? C2 C10 C9 106.57(15) . . ? C2 C10 C11 123.77(15) . . ? C9 C10 C11 129.61(14) . . ? C10 C11 C12 109.87(13) . . ? N13 C12 C11 109.96(14) . . ? C14 N13 C12 116.82(13) . . ? C14 N13 C1 125.68(13) . . ? C12 N13 C1 114.78(12) . . ? O14 C14 N13 120.28(16) . . ? O14 C14 C15 120.01(15) . . ? N13 C14 C15 119.71(14) . . ? C14 C15 C16 114.56(13) . . ? C15 C16 C23 110.94(13) . . ? C15 C16 C17 109.62(13) . . ? C23 C16 C17 113.31(13) . . ? C18 C17 C16 109.41(12) . . ? C18 C17 C1 114.00(12) . . ? C16 C17 C1 111.37(11) . . ? O18 C18 C19 119.75(14) . . ? O18 C18 C17 121.99(13) . . ? C19 C18 C17 118.24(13) . . ? C20 C19 C18 130.91(14) . . ? C20 C19 S1 111.52(11) . . ? C18 C19 S1 117.49(12) . . ? C19 C20 C21 110.60(17) . . ? C22 C21 C20 113.10(18) . . ? C21 C22 S1 113.07(14) . . ? C29 C28 C1 116.19(13) . . ? C28 C29 C30 111.42(13) . . ? C31 C30 C29 113.08(14) . . ? _diffrn_measured_fraction_theta_max 0.999 _diffrn_reflns_theta_full 27.45 _diffrn_measured_fraction_theta_full 0.999 _refine_diff_density_max 0.250 _refine_diff_density_min -0.501 _refine_diff_density_rms 0.043 #===================================================================== data_aka11 _database_code_depnum_ccdc_archive 'CCDC 281676' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common '6f in paper' _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C25 H28 N2 O2 S' _chemical_formula_weight 420.55 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' S S 0.1246 0.1234 '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)/n loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, y+1/2, -z+1/2' '-x, -y, -z' 'x-1/2, -y-1/2, z-1/2' _cell_length_a 8.62390(10) _cell_length_b 22.0514(4) _cell_length_c 13.22250(10) _cell_angle_alpha 90.00 _cell_angle_beta 100.1640(10) _cell_angle_gamma 90.00 _cell_volume 2475.05(6) _cell_formula_units_Z 4 _cell_measurement_temperature 200(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description polyhedron _exptl_crystal_colour colorless _exptl_crystal_size_max 0.50 _exptl_crystal_size_mid 0.26 _exptl_crystal_size_min 0.22 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.129 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 896 _exptl_absorpt_coefficient_mu 0.152 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.9278 _exptl_absorpt_correction_T_max 0.9673 _exptl_absorpt_process_details 'Blessing, Acta Cryst. (1995) A51 33-38.' _exptl_special_details ; ? ; _diffrn_ambient_temperature 200(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'CCD area detector' _diffrn_measurement_method 'phi and omega scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 25612 _diffrn_reflns_av_R_equivalents 0.0437 _diffrn_reflns_av_sigmaI/netI 0.0402 _diffrn_reflns_limit_h_min -11 _diffrn_reflns_limit_h_max 11 _diffrn_reflns_limit_k_min -28 _diffrn_reflns_limit_k_max 28 _diffrn_reflns_limit_l_min -17 _diffrn_reflns_limit_l_max 17 _diffrn_reflns_theta_min 1.85 _diffrn_reflns_theta_max 27.50 _reflns_number_total 5688 _reflns_number_gt 3739 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'Bruker SMART' _computing_data_reduction 'Bruker SHELXTL' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Bruker SHELXTL' _computing_publication_material 'Bruker SHELXTL' _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.1118P)^2^+1.2454P] 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_extinction_coef ? _refine_ls_number_reflns 5688 _refine_ls_number_parameters 324 _refine_ls_number_restraints 12 _refine_ls_R_factor_all 0.1031 _refine_ls_R_factor_gt 0.0675 _refine_ls_wR_factor_ref 0.2133 _refine_ls_wR_factor_gt 0.1907 _refine_ls_goodness_of_fit_ref 1.038 _refine_ls_restrained_S_all 1.039 _refine_ls_shift/su_max 0.034 _refine_ls_shift/su_mean 0.003 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 0.6209(3) 0.24617(11) 0.39581(17) 0.0322(5) Uani 1 1 d . . . C2 C 0.4777(3) 0.20884(11) 0.40663(17) 0.0314(5) Uani 1 1 d . . . N3 N 0.3925(2) 0.17647(9) 0.32682(15) 0.0345(5) Uani 1 1 d . . . H3 H 0.4061 0.1775 0.2624 0.041 Uiso 1 1 calc R . . C4 C 0.2823(3) 0.14219(11) 0.36474(18) 0.0350(5) Uani 1 1 d . . . C5 C 0.1730(3) 0.10041(12) 0.3151(2) 0.0408(6) Uani 1 1 d . . . H5 H 0.1657 0.0916 0.2441 0.049 Uiso 1 1 calc R . . C6 C 0.0757(3) 0.07229(12) 0.3739(2) 0.0475(7) Uani 1 1 d . . . H6 H 0.0005 0.0434 0.3426 0.057 Uiso 1 1 calc R . . C7 C 0.0860(3) 0.08549(13) 0.4780(2) 0.0482(7) Uani 1 1 d . . . H7 H 0.0170 0.0656 0.5158 0.058 Uiso 1 1 calc R . . C8 C 0.1928(3) 0.12627(12) 0.5269(2) 0.0423(6) Uani 1 1 d . . . H8 H 0.1975 0.1349 0.5978 0.051 Uiso 1 1 calc R . . C9 C 0.2960(3) 0.15532(11) 0.47095(18) 0.0350(5) Uani 1 1 d . . . C10 C 0.4214(3) 0.19782(11) 0.49565(17) 0.0340(5) Uani 1 1 d . . . C11 C 0.4818(3) 0.23215(12) 0.59195(18) 0.0402(6) Uani 1 1 d . . . H11A H 0.5631 0.2081 0.6370 0.048 Uiso 1 1 calc R . . H11B H 0.3948 0.2407 0.6297 0.048 Uiso 1 1 calc R . . C12 C 0.5519(3) 0.29100(12) 0.56152(19) 0.0403(6) Uani 1 1 d . . . H12A H 0.4672 0.3170 0.5240 0.048 Uiso 1 1 calc R . . H12B H 0.6021 0.3130 0.6240 0.048 Uiso 1 1 calc R . . N13 N 0.6706(2) 0.27893(10) 0.49546(14) 0.0358(5) Uani 1 1 d . . . C14 C 0.8218(3) 0.29551(12) 0.53115(18) 0.0389(6) Uani 1 1 d . . . O14 O 0.8576(2) 0.32451(10) 0.61198(13) 0.0529(5) Uani 1 1 d . . . C15 C 0.9548(3) 0.27719(13) 0.4755(2) 0.0436(6) Uani 1 1 d . . . H15 H 1.0267 0.2512 0.5252 0.052 Uiso 1 1 calc R . . C16 C 0.9079(3) 0.23856(12) 0.38000(18) 0.0371(6) Uani 1 1 d . . . H16A H 0.8899 0.2651 0.3186 0.045 Uiso 1 1 calc R . . H16B H 0.9950 0.2105 0.3733 0.045 Uiso 1 1 calc R . . C17 C 0.7601(3) 0.20236(11) 0.38436(18) 0.0341(5) Uani 1 1 d . . . H17 H 0.7814 0.1766 0.4476 0.041 Uiso 1 1 calc R . . C18 C 0.7254(3) 0.15976(12) 0.29233(19) 0.0371(6) Uani 1 1 d D A . O18 O 0.7410(2) 0.17735(9) 0.20704(13) 0.0481(5) Uani 1 1 d . . . C19 C 0.6779(3) 0.09709(13) 0.3076(2) 0.0422(6) Uani 1 1 d D . . S20 S 0.6517(5) 0.05068(11) 0.2063(3) 0.0687(8) Uani 0.605(6) 1 d PD A 1 C21 C 0.590(3) -0.0057(8) 0.2758(17) 0.086(7) Uani 0.605(6) 1 d PD A 1 H21 H 0.5514 -0.0432 0.2456 0.104 Uiso 0.605(6) 1 calc PR A 1 C22 C 0.597(2) 0.0056(6) 0.3756(12) 0.055(3) Uani 0.605(6) 1 d PD A 1 H22 H 0.5680 -0.0223 0.4237 0.066 Uiso 0.605(6) 1 calc PR A 1 C23 C 0.6555(18) 0.0649(7) 0.4001(12) 0.103(8) Uani 0.605(6) 1 d PD A 1 H23 H 0.6768 0.0814 0.4675 0.124 Uiso 0.605(6) 1 calc PR A 1 C24 C 0.5839(3) 0.29121(12) 0.30506(18) 0.0371(6) Uani 1 1 d . . . H24A H 0.6762 0.3181 0.3063 0.045 Uiso 1 1 calc R . . H24B H 0.5700 0.2679 0.2401 0.045 Uiso 1 1 calc R . . C25 C 0.4387(3) 0.33065(13) 0.3041(2) 0.0437(6) Uani 1 1 d . . . H25A H 0.3453 0.3042 0.3018 0.052 Uiso 1 1 calc R . . H25B H 0.4516 0.3544 0.3685 0.052 Uiso 1 1 calc R . . C26 C 0.4102(4) 0.37374(14) 0.2132(2) 0.0537(7) Uani 1 1 d . . . H26A H 0.3979 0.3499 0.1489 0.064 Uiso 1 1 calc R . . H26B H 0.5037 0.4001 0.2158 0.064 Uiso 1 1 calc R . . C27 C 0.2655(4) 0.41328(15) 0.2109(3) 0.0656(9) Uani 1 1 d . . . H27A H 0.2532 0.4400 0.1508 0.098 Uiso 1 1 calc R . . H27B H 0.2779 0.4378 0.2736 0.098 Uiso 1 1 calc R . . H27C H 0.1720 0.3875 0.2068 0.098 Uiso 1 1 calc R . . C28 C 1.0521(4) 0.33148(17) 0.4561(3) 0.0688(10) Uani 1 1 d . . . H28A H 1.0805 0.3549 0.5197 0.103 Uiso 1 1 calc R . . H28B H 0.9909 0.3571 0.4030 0.103 Uiso 1 1 calc R . . H28C H 1.1482 0.3177 0.4331 0.103 Uiso 1 1 calc R . . S20B S 0.6557(6) 0.06646(18) 0.4201(4) 0.0489(9) Uani 0.395(6) 1 d PD A 2 C21B C 0.624(4) -0.0032(10) 0.371(2) 0.094(11) Uani 0.395(6) 1 d PD A 2 C22B C 0.619(5) -0.0052(11) 0.2691(19) 0.074(7) Uani 0.395(6) 1 d PD A 2 C23B C 0.630(4) 0.0534(10) 0.2262(17) 0.126(15) Uani 0.395(6) 1 d PD A 2 C80 C 0.782(3) 0.5214(10) 0.5375(16) 0.388(10) Uiso 1 1 d . . . C81 C 0.7343(11) 0.4651(4) 0.5186(7) 0.162(3) Uiso 1 1 d . . . C82 C 0.5646(17) 0.4829(6) 0.5141(12) 0.266(6) Uiso 1 1 d . . . C83 C 0.679(2) 0.4466(7) 0.4364(13) 0.299(7) Uiso 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 0.0319(11) 0.0400(13) 0.0257(11) -0.0020(9) 0.0079(9) 0.0007(10) C2 0.0285(11) 0.0413(13) 0.0250(11) -0.0007(9) 0.0064(9) 0.0028(10) N3 0.0323(10) 0.0460(12) 0.0262(10) 0.0007(8) 0.0075(8) 0.0023(9) C4 0.0283(11) 0.0396(13) 0.0379(13) 0.0032(10) 0.0082(10) 0.0062(10) C5 0.0326(12) 0.0448(14) 0.0436(14) -0.0027(11) 0.0029(11) 0.0048(11) C6 0.0329(13) 0.0434(15) 0.0659(19) 0.0014(13) 0.0080(12) 0.0017(11) C7 0.0351(14) 0.0528(16) 0.0592(18) 0.0124(13) 0.0148(12) -0.0005(12) C8 0.0362(13) 0.0513(15) 0.0423(14) 0.0114(12) 0.0147(11) 0.0052(12) C9 0.0304(12) 0.0419(13) 0.0340(12) 0.0054(10) 0.0093(9) 0.0064(10) C10 0.0330(12) 0.0426(13) 0.0278(11) 0.0033(10) 0.0092(9) 0.0052(10) C11 0.0405(13) 0.0556(15) 0.0268(12) 0.0003(11) 0.0120(10) 0.0024(12) C12 0.0394(13) 0.0527(15) 0.0308(12) -0.0084(11) 0.0118(10) 0.0020(11) N13 0.0372(11) 0.0469(12) 0.0254(10) -0.0046(8) 0.0111(8) -0.0003(9) C14 0.0404(14) 0.0486(14) 0.0281(12) 0.0013(10) 0.0066(10) -0.0042(11) O14 0.0521(12) 0.0758(14) 0.0306(9) -0.0121(9) 0.0064(8) -0.0119(10) C15 0.0351(13) 0.0607(17) 0.0349(13) -0.0014(12) 0.0055(10) -0.0051(12) C16 0.0304(12) 0.0481(14) 0.0344(13) 0.0007(11) 0.0101(10) 0.0023(10) C17 0.0323(12) 0.0419(13) 0.0291(12) 0.0017(10) 0.0084(9) 0.0011(10) C18 0.0294(12) 0.0467(14) 0.0364(13) -0.0001(10) 0.0086(10) 0.0039(10) O18 0.0557(12) 0.0567(12) 0.0339(10) -0.0038(8) 0.0135(8) -0.0043(9) C19 0.0369(14) 0.0446(15) 0.0457(15) 0.0015(12) 0.0086(12) 0.0062(12) S20 0.0840(19) 0.0472(10) 0.0692(12) -0.0137(9) -0.0018(11) -0.0030(11) C21 0.085(11) 0.054(8) 0.130(14) -0.017(7) 0.042(8) -0.033(6) C22 0.042(5) 0.044(4) 0.082(6) 0.017(4) 0.022(4) 0.014(5) C23 0.038(6) 0.120(12) 0.150(16) -0.072(10) 0.014(6) -0.001(6) C24 0.0376(13) 0.0458(14) 0.0302(12) 0.0021(10) 0.0118(10) 0.0030(11) C25 0.0443(14) 0.0515(15) 0.0373(13) 0.0071(11) 0.0129(11) 0.0099(12) C26 0.0587(18) 0.0590(17) 0.0450(16) 0.0147(13) 0.0138(13) 0.0169(15) C27 0.067(2) 0.0605(19) 0.068(2) 0.0135(16) 0.0108(17) 0.0230(16) C28 0.064(2) 0.092(3) 0.0557(19) -0.0228(18) 0.0252(16) -0.0344(19) S20B 0.0391(18) 0.0427(15) 0.0644(17) 0.0113(13) 0.0077(11) 0.0002(13) C21B 0.071(16) 0.078(13) 0.136(19) 0.020(11) 0.026(10) 0.042(8) C22B 0.084(17) 0.060(13) 0.073(12) -0.010(8) 0.001(10) -0.003(9) C23B 0.087(13) 0.14(2) 0.15(3) 0.014(16) 0.009(13) -0.055(14) _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 N13 1.497(3) . ? C1 C2 1.512(3) . ? C1 C24 1.547(3) . ? C1 C17 1.569(3) . ? C2 C10 1.372(3) . ? C2 N3 1.375(3) . ? N3 C4 1.376(3) . ? C4 C5 1.396(4) . ? C4 C9 1.418(3) . ? C5 C6 1.387(4) . ? C6 C7 1.394(4) . ? C7 C8 1.366(4) . ? C8 C9 1.408(3) . ? C9 C10 1.425(4) . ? C10 C11 1.494(3) . ? C11 C12 1.516(4) . ? C12 N13 1.482(3) . ? N13 C14 1.356(3) . ? C14 O14 1.237(3) . ? C14 C15 1.522(4) . ? C15 C28 1.510(4) . ? C15 C16 1.518(4) . ? C16 C17 1.514(3) . ? C17 C18 1.525(3) . ? C18 O18 1.222(3) . ? C18 C19 1.465(4) . ? C19 C23B 1.448(18) . ? C19 C23 1.456(14) . ? C19 S20 1.669(4) . ? C19 S20B 1.676(5) . ? S20 C21 1.69(2) . ? C21 C22 1.334(12) . ? C22 C23 1.42(2) . ? C24 C25 1.523(3) . ? C25 C26 1.517(4) . ? C26 C27 1.518(4) . ? S20B C21B 1.67(3) . ? C21B C22B 1.342(15) . ? C22B C23B 1.42(3) . ? C80 C81 1.32(2) . ? C80 C82 2.03(2) . ? C81 C83 1.180(16) . ? C81 C82 1.507(14) . ? C82 C82 1.34(3) 3_666 ? C82 C83 1.742(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 N13 C1 C2 106.93(17) . . ? N13 C1 C24 111.14(19) . . ? C2 C1 C24 111.27(19) . . ? N13 C1 C17 106.08(18) . . ? C2 C1 C17 109.00(18) . . ? C24 C1 C17 112.16(18) . . ? C10 C2 N3 110.2(2) . . ? C10 C2 C1 126.6(2) . . ? N3 C2 C1 123.02(19) . . ? C2 N3 C4 108.38(19) . . ? N3 C4 C5 130.0(2) . . ? N3 C4 C9 107.8(2) . . ? C5 C4 C9 122.1(2) . . ? C6 C5 C4 117.2(2) . . ? C5 C6 C7 121.4(3) . . ? C8 C7 C6 121.7(3) . . ? C7 C8 C9 119.1(3) . . ? C8 C9 C4 118.5(2) . . ? C8 C9 C10 134.7(2) . . ? C4 C9 C10 106.8(2) . . ? C2 C10 C9 106.8(2) . . ? C2 C10 C11 121.3(2) . . ? C9 C10 C11 131.7(2) . . ? C10 C11 C12 107.64(19) . . ? N13 C12 C11 110.6(2) . . ? C14 N13 C12 117.91(19) . . ? C14 N13 C1 122.99(19) . . ? C12 N13 C1 119.01(19) . . ? O14 C14 N13 121.2(2) . . ? O14 C14 C15 117.4(2) . . ? N13 C14 C15 121.4(2) . . ? C28 C15 C16 112.2(2) . . ? C28 C15 C14 111.1(2) . . ? C16 C15 C14 116.0(2) . . ? C17 C16 C15 111.52(19) . . ? C16 C17 C18 110.03(18) . . ? C16 C17 C1 110.04(19) . . ? C18 C17 C1 114.26(19) . . ? O18 C18 C19 120.4(2) . . ? O18 C18 C17 120.2(2) . . ? C19 C18 C17 119.4(2) . . ? C23B C19 C23 103.8(14) . . ? C23B C19 C18 125.0(10) . . ? C23 C19 C18 131.1(7) . . ? C23B C19 S20 10.1(13) . . ? C23 C19 S20 110.8(7) . . ? C18 C19 S20 118.0(2) . . ? C23B C19 S20B 109.3(9) . . ? C23 C19 S20B 5.6(8) . . ? C18 C19 S20B 125.5(3) . . ? S20 C19 S20B 116.4(3) . . ? C19 S20 C21 91.5(7) . . ? C22 C21 S20 115.8(15) . . ? C21 C22 C23 110.6(14) . . ? C22 C23 C19 110.6(13) . . ? C25 C24 C1 115.47(19) . . ? C26 C25 C24 112.5(2) . . ? C25 C26 C27 113.2(2) . . ? C21B S20B C19 93.6(10) . . ? C22B C21B S20B 113(2) . . ? C21B C22B C23B 112(2) . . ? C22B C23B C19 109.7(17) . . ? C81 C80 C82 47.9(9) . . ? C83 C81 C80 124.2(16) . . ? C83 C81 C82 79.8(10) . . ? C80 C81 C82 91.7(12) . . ? C82 C82 C81 156(2) 3_666 . ? C82 C82 C83 128.7(19) 3_666 . ? C81 C82 C83 41.8(7) . . ? C82 C82 C80 120.4(17) 3_666 . ? C81 C82 C80 40.4(7) . . ? C83 C82 C80 71.2(10) . . ? C81 C83 C82 58.3(9) . . ? _diffrn_measured_fraction_theta_max 0.998 _diffrn_reflns_theta_full 27.50 _diffrn_measured_fraction_theta_full 0.998 _refine_diff_density_max 0.650 _refine_diff_density_min -0.584 _refine_diff_density_rms 0.059 #===================================================================== data_aka12 _database_code_depnum_ccdc_archive 'CCDC 281677' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common '6l in paper' _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C18 H20 N2 O3' _chemical_formula_weight 312.36 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)/c loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y-1/2, z-1/2' _cell_length_a 11.5257(3) _cell_length_b 12.9651(4) _cell_length_c 10.7417(3) _cell_angle_alpha 90.00 _cell_angle_beta 94.7700(10) _cell_angle_gamma 90.00 _cell_volume 1599.59(8) _cell_formula_units_Z 4 _cell_measurement_temperature 200(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description polyhedron _exptl_crystal_colour colorless _exptl_crystal_size_max 0.42 _exptl_crystal_size_mid 0.22 _exptl_crystal_size_min 0.16 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.297 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 664 _exptl_absorpt_coefficient_mu 0.089 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.9636 _exptl_absorpt_correction_T_max 0.9859 _exptl_absorpt_process_details 'Blessing, Acta Cryst. (1995) A51 33-38.' _exptl_special_details ; ? ; _diffrn_ambient_temperature 200(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'CCD area detector' _diffrn_measurement_method 'phi and omega scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 16235 _diffrn_reflns_av_R_equivalents 0.0298 _diffrn_reflns_av_sigmaI/netI 0.0221 _diffrn_reflns_limit_h_min -14 _diffrn_reflns_limit_h_max 14 _diffrn_reflns_limit_k_min -16 _diffrn_reflns_limit_k_max 16 _diffrn_reflns_limit_l_min -13 _diffrn_reflns_limit_l_max 13 _diffrn_reflns_theta_min 1.77 _diffrn_reflns_theta_max 27.47 _reflns_number_total 3648 _reflns_number_gt 3011 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'Bruker SMART' _computing_data_reduction 'Bruker SHELXTL' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Bruker SHELXTL' _computing_publication_material 'Bruker SHELXTL' _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0542P)^2^+0.2897P] 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 refall _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 3648 _refine_ls_number_parameters 288 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0460 _refine_ls_R_factor_gt 0.0358 _refine_ls_wR_factor_ref 0.0959 _refine_ls_wR_factor_gt 0.0893 _refine_ls_goodness_of_fit_ref 1.028 _refine_ls_restrained_S_all 1.028 _refine_ls_shift/su_max 0.001 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group C1 C 1.05828(9) 0.16742(8) -0.11925(10) 0.0213(2) Uani 1 1 d . . . H1 H 1.0751(11) 0.1388(10) -0.0344(12) 0.024(3) Uiso 1 1 d . . . C2 C 1.16894(9) 0.16403(8) -0.18441(10) 0.0210(2) Uani 1 1 d . . . N3 N 1.21097(8) 0.07728(7) -0.23980(9) 0.0234(2) Uani 1 1 d . . . H3 H 1.1693(13) 0.0217(13) -0.2639(14) 0.042(4) Uiso 1 1 d . . . C4 C 1.31932(9) 0.10028(9) -0.27743(10) 0.0239(2) Uani 1 1 d . . . C5 C 1.39686(10) 0.03766(10) -0.33634(11) 0.0306(3) Uani 1 1 d . . . H5 H 1.3734(12) -0.0332(12) -0.3599(13) 0.036(4) Uiso 1 1 d . . . C6 C 1.50236(11) 0.08061(11) -0.36132(12) 0.0370(3) Uani 1 1 d . . . H6 H 1.5605(14) 0.0396(13) -0.4001(15) 0.050(4) Uiso 1 1 d . . . C7 C 1.52989(11) 0.18275(12) -0.32971(13) 0.0399(3) Uani 1 1 d . . . H7 H 1.6053(16) 0.2109(13) -0.3516(16) 0.058(5) Uiso 1 1 d . . . C8 C 1.45356(10) 0.24491(10) -0.27128(12) 0.0336(3) Uani 1 1 d . . . H8 H 1.4732(13) 0.3155(12) -0.2475(14) 0.043(4) Uiso 1 1 d . . . C9 C 1.34597(9) 0.20347(9) -0.24337(10) 0.0248(2) Uani 1 1 d . . . C10 C 1.24845(9) 0.24228(8) -0.18312(10) 0.0236(2) Uani 1 1 d . . . C11 C 1.23052(10) 0.34412(9) -0.12086(12) 0.0292(3) Uani 1 1 d . . . H11A H 1.2128(12) 0.3981(11) -0.1833(13) 0.033(3) Uiso 1 1 d . . . H11B H 1.3023(14) 0.3642(12) -0.0717(14) 0.044(4) Uiso 1 1 d . . . C12 C 1.13104(10) 0.33443(9) -0.03597(11) 0.0273(2) Uani 1 1 d . . . H12A H 1.1583(11) 0.2945(10) 0.0389(12) 0.027(3) Uiso 1 1 d . . . H12B H 1.1023(12) 0.4030(11) -0.0114(13) 0.033(3) Uiso 1 1 d . . . N13 N 1.03266(8) 0.27778(7) -0.10032(8) 0.0229(2) Uani 1 1 d . . . C14 C 0.94147(10) 0.33003(9) -0.15535(10) 0.0266(2) Uani 1 1 d . . . O14 O 0.93102(8) 0.42410(6) -0.14054(9) 0.0392(2) Uani 1 1 d . . . C15 C 0.85010(10) 0.27087(10) -0.23490(12) 0.0325(3) Uani 1 1 d . . . H15A H 0.7835(14) 0.2552(12) -0.1834(14) 0.042(4) Uiso 1 1 d . . . H15B H 0.8196(13) 0.3176(12) -0.2984(14) 0.041(4) Uiso 1 1 d . . . C16 C 0.89521(11) 0.17228(10) -0.28935(11) 0.0309(3) Uani 1 1 d . . . H16A H 0.8325(13) 0.1323(11) -0.3354(13) 0.037(4) Uiso 1 1 d . . . H16B H 0.9544(13) 0.1892(11) -0.3494(13) 0.038(4) Uiso 1 1 d . . . C17 C 0.95564(9) 0.10839(8) -0.18369(10) 0.0234(2) Uani 1 1 d . . . H17 H 0.9858(11) 0.0452(10) -0.2160(12) 0.026(3) Uiso 1 1 d . . . C18 C 0.87260(9) 0.07496(8) -0.08807(10) 0.0231(2) Uani 1 1 d . . . O18 O 0.89367(7) 0.07753(7) 0.02367(8) 0.0325(2) Uani 1 1 d . . . C19 C 0.68612(11) 0.00263(11) -0.06301(13) 0.0358(3) Uani 1 1 d . . . H19A H 0.7272(14) -0.0425(13) 0.0014(15) 0.047(4) Uiso 1 1 d . . . H19B H 0.6325(14) -0.0392(12) -0.1206(15) 0.047(4) Uiso 1 1 d . . . O19 O 0.77278(7) 0.03963(7) -0.14456(8) 0.0318(2) Uani 1 1 d . . . C20 C 0.62293(13) 0.09011(14) -0.00824(15) 0.0452(3) Uani 1 1 d . . . H20A H 0.6764(18) 0.1358(16) 0.0355(18) 0.070(6) Uiso 1 1 d . . . H20B H 0.5730(17) 0.0615(14) 0.0538(18) 0.066(5) Uiso 1 1 d . . . H20C H 0.5750(19) 0.1261(16) -0.072(2) 0.079(6) Uiso 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 0.0210(5) 0.0196(5) 0.0234(5) 0.0013(4) 0.0032(4) 0.0006(4) C2 0.0200(5) 0.0199(5) 0.0232(5) 0.0008(4) 0.0018(4) 0.0006(4) N3 0.0208(4) 0.0213(5) 0.0287(5) -0.0008(4) 0.0049(4) -0.0009(4) C4 0.0204(5) 0.0281(5) 0.0233(5) 0.0037(4) 0.0019(4) 0.0007(4) C5 0.0273(6) 0.0345(7) 0.0305(6) 0.0001(5) 0.0043(5) 0.0053(5) C6 0.0256(6) 0.0518(8) 0.0346(7) 0.0008(6) 0.0079(5) 0.0081(5) C7 0.0217(6) 0.0549(8) 0.0440(7) 0.0067(6) 0.0081(5) -0.0039(5) C8 0.0241(6) 0.0373(7) 0.0393(7) 0.0047(5) 0.0022(5) -0.0066(5) C9 0.0212(5) 0.0279(6) 0.0251(5) 0.0031(4) 0.0003(4) -0.0012(4) C10 0.0220(5) 0.0229(5) 0.0257(5) 0.0015(4) 0.0011(4) -0.0018(4) C11 0.0288(6) 0.0239(6) 0.0348(6) -0.0033(5) 0.0026(5) -0.0056(4) C12 0.0287(6) 0.0240(6) 0.0287(6) -0.0047(4) 0.0001(5) -0.0005(4) N13 0.0227(4) 0.0201(4) 0.0258(5) -0.0014(3) 0.0018(4) 0.0016(3) C14 0.0263(6) 0.0258(6) 0.0282(6) 0.0077(4) 0.0053(4) 0.0029(4) O14 0.0415(5) 0.0244(4) 0.0513(6) 0.0064(4) 0.0008(4) 0.0084(4) C15 0.0259(6) 0.0346(6) 0.0360(7) 0.0126(5) -0.0039(5) -0.0001(5) C16 0.0271(6) 0.0426(7) 0.0230(6) 0.0022(5) 0.0011(5) -0.0087(5) C17 0.0209(5) 0.0233(5) 0.0267(5) -0.0036(4) 0.0063(4) -0.0019(4) C18 0.0213(5) 0.0187(5) 0.0299(6) -0.0003(4) 0.0051(4) 0.0010(4) O18 0.0274(4) 0.0428(5) 0.0275(4) 0.0045(3) 0.0043(3) -0.0037(3) C19 0.0268(6) 0.0437(7) 0.0379(7) 0.0025(6) 0.0087(5) -0.0122(5) O19 0.0245(4) 0.0408(5) 0.0310(4) -0.0039(4) 0.0077(3) -0.0109(3) C20 0.0280(7) 0.0648(10) 0.0439(8) -0.0013(7) 0.0092(6) 0.0003(7) _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 N13 1.4784(13) . ? C1 C2 1.5056(14) . ? C1 C17 1.5259(15) . ? C2 C10 1.3664(15) . ? C2 N3 1.3790(14) . ? N3 C4 1.3769(14) . ? C4 C5 1.3972(16) . ? C4 C9 1.4140(16) . ? C5 C6 1.3838(18) . ? C6 C7 1.397(2) . ? C7 C8 1.3817(19) . ? C8 C9 1.4064(16) . ? C9 C10 1.4340(15) . ? C10 C11 1.5021(16) . ? C11 C12 1.5283(17) . ? C12 N13 1.4740(14) . ? N13 C14 1.3453(14) . ? C14 O14 1.2371(14) . ? C14 C15 1.5093(17) . ? C15 C16 1.5156(19) . ? C16 C17 1.5257(16) . ? C17 C18 1.5240(15) . ? C18 O18 1.2051(14) . ? C18 O19 1.3362(13) . ? C19 O19 1.4631(14) . ? C19 C20 1.495(2) . ? 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 N13 C1 C2 106.19(8) . . ? N13 C1 C17 113.06(8) . . ? C2 C1 C17 115.42(9) . . ? C10 C2 N3 110.52(9) . . ? C10 C2 C1 124.54(9) . . ? N3 C2 C1 124.47(9) . . ? C4 N3 C2 108.05(9) . . ? N3 C4 C5 129.57(11) . . ? N3 C4 C9 108.16(9) . . ? C5 C4 C9 122.25(10) . . ? C6 C5 C4 117.35(12) . . ? C5 C6 C7 121.33(12) . . ? C8 C7 C6 121.53(12) . . ? C7 C8 C9 118.68(12) . . ? C8 C9 C4 118.86(11) . . ? C8 C9 C10 134.44(11) . . ? C4 C9 C10 106.69(9) . . ? C2 C10 C9 106.57(10) . . ? C2 C10 C11 122.69(10) . . ? C9 C10 C11 130.65(10) . . ? C10 C11 C12 109.34(9) . . ? N13 C12 C11 110.32(9) . . ? C14 N13 C12 119.84(9) . . ? C14 N13 C1 125.78(9) . . ? C12 N13 C1 113.09(8) . . ? O14 C14 N13 121.38(11) . . ? O14 C14 C15 120.20(10) . . ? N13 C14 C15 118.41(10) . . ? C14 C15 C16 113.67(10) . . ? C15 C16 C17 108.72(9) . . ? C18 C17 C16 112.48(9) . . ? C18 C17 C1 110.10(9) . . ? C16 C17 C1 110.72(9) . . ? O18 C18 O19 123.81(10) . . ? O18 C18 C17 125.28(10) . . ? O19 C18 C17 110.90(9) . . ? O19 C19 C20 111.47(11) . . ? C18 O19 C19 116.45(9) . . ? _diffrn_measured_fraction_theta_max 0.999 _diffrn_reflns_theta_full 27.47 _diffrn_measured_fraction_theta_full 0.999 _refine_diff_density_max 0.193 _refine_diff_density_min -0.241 _refine_diff_density_rms 0.045 #===================================================================== #_eof # End of Crystallographic Information File