############################################################################## # # # This CIF contains the data in a paper accepted for publication in # # Acta Crystallographica Section E. It conforms to the requirements of # # Notes for Authors for Acta Crystallographica Section E, and has been # # peer reviewed under the auspices of the IUCr Commission on Journals. # # # # Full details of the Crystallographic Information File format # # are given in the paper "The Crystallographic Information File (CIF): # # a New Standard Archive File for Crystallography" by S. R. Hall, F. H. # # Allen and I. D. Brown [Acta Cryst. (1991), A47, 655-685]. # # # # The current version of the core CIF dictionary is obtainable from # # ftp://ftp.iucr.org/pub/cif_core.dic. # # # # Software is freely available for graphical display of the structure(s) # # in this CIF. For information consult the CIF software page # # http://www.iucr.org/resources/cif/software. # # # # This file may be used for bona fide research purposes within the # # scientific community so long as proper attribution is given to the journal # # article from which it was obtained. # # # ############################################################################## data_I _database_code_depnum_ccdc_archive 'CCDC 1409635' _audit_creation_method SHELXL-97 _chemical_name_systematic ; (1\a,14\a,16\b)-20-Ethyl-8,9,10-trihydroxy-1,14,16-trimethoxyaconitan-4-yl 2-aminobenzoate ; _chemical_name_common ; Sepaconitine ; _chemical_formula_moiety 'C30 H42 N2 O8' _chemical_formula_sum 'C30 H42 N2 O8' _chemical_formula_iupac 'C30 H42 N2 O8' _chemical_formula_weight 558.66 _chemical_melting_point ? _chemical_melting_point_gt 250 _chemical_melting_point_lt 252 _symmetry_cell_setting orthorhombic _symmetry_space_group_name_H-M 'P 21 21 21' _symmetry_space_group_name_Hall 'P 2ac 2ab' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, -y, z+1/2' 'x+1/2, -y+1/2, -z' '-x, y+1/2, -z+1/2' _cell_length_a 9.6917(5) _cell_length_b 16.0510(7) _cell_length_c 18.3549(7) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 2855.3(2) _cell_formula_units_Z 4 _cell_measurement_reflns_used 2628 _cell_measurement_theta_min 3.66 _cell_measurement_theta_max 64.24 _cell_measurement_temperature 173(2) _exptl_crystal_description block _exptl_crystal_colour colorless _exptl_crystal_size_max 0.32 _exptl_crystal_size_mid 0.32 _exptl_crystal_size_min 0.28 _exptl_crystal_density_diffrn 1.300 _exptl_crystal_density_meas ? _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1200 _exptl_absorpt_coefficient_mu 0.771 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details ; (SADABS; Bruker, 2002) ; _exptl_absorpt_correction_T_min 0.7905 _exptl_absorpt_correction_T_max 0.8131 _exptl_special_details ? _diffrn_ambient_temperature 173(2) _diffrn_radiation_type CuK\a _diffrn_radiation_wavelength 1.54178 _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Bruker SMART CCD area-detector' _diffrn_measurement_method 'phi and omega scans' _diffrn_detector_area_resol_mean ? _diffrn_reflns_number 8125 _diffrn_reflns_av_R_equivalents 0.0291 _diffrn_reflns_av_sigmaI/netI 0.0434 _diffrn_reflns_theta_min 3.66 _diffrn_reflns_theta_max 64.99 _diffrn_reflns_theta_full 64.99 _diffrn_measured_fraction_theta_max 0.982 _diffrn_measured_fraction_theta_full 0.982 _diffrn_reflns_limit_h_min -7 _diffrn_reflns_limit_h_max 11 _diffrn_reflns_limit_k_min -18 _diffrn_reflns_limit_k_max 18 _diffrn_reflns_limit_l_min -21 _diffrn_reflns_limit_l_max 18 _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_decay_% ? _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^ > \s(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. ; _reflns_number_total 4528 _reflns_number_gt 3831 _reflns_threshold_expression I>2sigma(I) _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_R_factor_all 0.0548 _refine_ls_R_factor_gt 0.0461 _refine_ls_wR_factor_gt 0.1197 _refine_ls_wR_factor_ref 0.1259 _refine_ls_goodness_of_fit_ref 1.046 _refine_ls_restrained_S_all 1.060 _refine_ls_number_reflns 4528 _refine_ls_number_parameters 388 _refine_ls_number_restraints 60 _refine_ls_hydrogen_treatment constr _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0752P)^2^+0.0411P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_hydrogens geom _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _refine_ls_shift/su_max 0.001 _refine_ls_shift/su_mean 0.000 _refine_diff_density_max 0.463 _refine_diff_density_min -0.192 _refine_ls_extinction_method none _refine_ls_extinction_coef ? loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source 'C' 'C' 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 'H' 'H' 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 'N' 'N' 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 'O' 'O' 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _computing_data_collection ; SMART (Bruker, 2002) ; _computing_cell_refinement ; SAINT (Bruker, 2002) ; _computing_data_reduction ; SAINT (Bruker, 2002) ; _computing_structure_solution ; SHELXTL (Sheldrick, 2008) ; _computing_structure_refinement ; SHELXTL (Sheldrick, 2008) ; _computing_molecular_graphics ; SHELXTL (Sheldrick, 2008) ; _computing_publication_material ; SHELXTL (Sheldrick, 2008) ; loop_ _atom_site_type_symbol _atom_site_label _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_calc_flag _atom_site_refinement_flags _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_disorder_assembly _atom_site_disorder_group C C1 0.5519(3) 0.04441(18) 0.93627(14) 0.0459(6) Uani d . 1 1 . . H H1 0.5224 0.0713 0.9829 0.055 Uiso calc R 1 1 . . C C2 0.5401(3) -0.04952(19) 0.94729(17) 0.0574(7) Uani d . 1 1 . . H H2A 0.4494 -0.0626 0.9693 0.069 Uiso calc R 1 1 . . H H2B 0.5451 -0.0777 0.8994 0.069 Uiso calc R 1 1 . . C C3 0.6545(3) -0.08242(19) 0.99638(17) 0.0587(7) Uani d . 1 1 . . H H3A 0.6440 -0.0598 1.0462 0.070 Uiso calc R 1 1 . . H H3B 0.6503 -0.1440 0.9990 0.070 Uiso calc R 1 1 . . C C4 0.7912(3) -0.05507(17) 0.96421(14) 0.0472(6) Uani d . 1 1 . . C C5 0.8106(3) 0.03991(16) 0.96718(13) 0.0417(6) Uani d . 1 1 . . H H5 0.8054 0.0615 1.0182 0.050 Uiso calc R 1 1 . . C C6 0.9497(3) 0.06134(17) 0.93102(14) 0.0457(6) Uani d . 1 1 . . H H6A 1.0101 0.0117 0.9287 0.055 Uiso calc R 1 1 . . H H6B 0.9979 0.1059 0.9583 0.055 Uiso calc R 1 1 . . C C7 0.9109(3) 0.09122(16) 0.85379(13) 0.0443(6) Uani d . 1 1 . . H H7 0.9740 0.0659 0.8168 0.053 Uiso calc R 1 1 . . C C8 0.9157(3) 0.18622(16) 0.84910(14) 0.0445(6) Uani d . 1 1 . . C C9 0.8267(3) 0.22508(16) 0.91195(13) 0.0416(6) Uani d . 1 1 . . C C10 0.6911(3) 0.17703(16) 0.92456(12) 0.0405(6) Uani d . 1 1 . . C C11 0.6968(3) 0.07934(16) 0.91761(13) 0.0399(5) Uani d . 1 1 . . C C12 0.5904(3) 0.22027(18) 0.87023(15) 0.0496(6) Uani d . 1 1 . . H H12A 0.5568 0.1796 0.8338 0.060 Uiso calc R 1 1 . . H H12B 0.5098 0.2431 0.8967 0.060 Uiso calc R 1 1 . . C C13 0.6700(3) 0.29100(18) 0.83222(15) 0.0527(7) Uani d . 1 1 B . H H13 0.6084 0.3399 0.8230 0.063 Uiso calc R 1 1 . . C C14 0.7783(3) 0.31184(17) 0.88965(15) 0.0512(7) Uani d . 1 1 . . H H14 0.7319 0.3389 0.9322 0.061 Uiso calc R 1 1 . . C C15 0.8737(3) 0.2179(2) 0.77238(14) 0.0565(7) Uani d . 1 1 B . H H15A 0.9459 0.2574 0.7560 0.068 Uiso calc R 1 1 . . H H15B 0.8767 0.1696 0.7389 0.068 Uiso calc R 1 1 . . C C16 0.7352(4) 0.2605(2) 0.76183(15) 0.0604(8) Uani d . 1 1 . . H H16 0.6702 0.2225 0.7356 0.073 Uiso calc R 1 1 A 1 C C17 0.7620(3) 0.05823(16) 0.84348(12) 0.0415(6) Uani d . 1 1 . . H H17 0.7146 0.0900 0.8039 0.050 Uiso calc R 1 1 . . C C18 0.8127(3) -0.08526(17) 0.88536(14) 0.0515(7) Uani d . 1 1 . . H H18A 0.9130 -0.0893 0.8758 0.062 Uiso calc R 1 1 . . H H18B 0.7734 -0.1419 0.8806 0.062 Uiso calc R 1 1 . . C C19 0.9371(3) -0.08098(19) 1.07202(15) 0.0556(7) Uani d . 1 1 . . C C20 0.3182(3) 0.0800(3) 0.9099(2) 0.0738(10) Uani d . 1 1 . . H H20A 0.2839 0.0276 0.9305 0.111 Uiso calc R 1 1 . . H H20B 0.2567 0.0982 0.8706 0.111 Uiso calc R 1 1 . . H H20C 0.3209 0.1227 0.9480 0.111 Uiso calc R 1 1 . . C C21 0.8619(4) 0.4468(2) 0.8583(2) 0.0807(10) Uani d . 1 1 . . H H21A 0.8080 0.4534 0.8135 0.121 Uiso calc R 1 1 . . H H21B 0.9477 0.4788 0.8543 0.121 Uiso calc R 1 1 . . H H21C 0.8081 0.4672 0.8999 0.121 Uiso calc R 1 1 . . C C22 0.7499(12) 0.3113(7) 0.6432(4) 0.114(3) Uani d PU 0.578(12) 1 B 1 H H22A 0.8162 0.2697 0.6260 0.170 Uiso calc PR 0.578(12) 1 B 1 H H22B 0.7575 0.3617 0.6134 0.170 Uiso calc PR 0.578(12) 1 B 1 H H22C 0.6561 0.2888 0.6393 0.170 Uiso calc PR 0.578(12) 1 B 1 C C22' 0.6743(13) 0.3573(9) 0.6707(7) 0.104(4) Uani d PU 0.422(12) 1 B 2 H H22D 0.6386 0.3124 0.6398 0.155 Uiso calc PR 0.422(12) 1 B 2 H H22E 0.7364 0.3927 0.6421 0.155 Uiso calc PR 0.422(12) 1 B 2 H H22F 0.5972 0.3909 0.6890 0.155 Uiso calc PR 0.422(12) 1 B 2 C C23 0.7964(4) -0.0559(2) 0.75690(15) 0.0625(8) Uani d . 1 1 . . H H23A 0.8964 -0.0683 0.7583 0.075 Uiso calc R 1 1 . . H H23B 0.7822 -0.0086 0.7230 0.075 Uiso calc R 1 1 . . C C24 0.7206(6) -0.1305(2) 0.7287(2) 0.0994(14) Uani d . 1 1 . . H H24A 0.7516 -0.1803 0.7548 0.149 Uiso calc R 1 1 . . H H24B 0.7394 -0.1371 0.6765 0.149 Uiso calc R 1 1 . . H H24C 0.6213 -0.1229 0.7362 0.149 Uiso calc R 1 1 . . C C1' 1.0692(3) -0.11619(17) 1.09396(15) 0.0525(7) Uani d . 1 1 . . C C2' 1.1153(4) -0.10849(19) 1.16724(16) 0.0600(8) Uani d . 1 1 . . C C3' 1.2446(4) -0.1426(2) 1.1845(2) 0.0732(10) Uani d . 1 1 . . H H3' 1.2769 -0.1389 1.2333 0.088 Uiso calc R 1 1 . . C C4' 1.3246(4) -0.1804(2) 1.1341(2) 0.0786(11) Uani d . 1 1 . . H H4' 1.4116 -0.2025 1.1480 0.094 Uiso calc R 1 1 . . C C5' 1.2809(4) -0.1874(2) 1.0619(2) 0.0739(9) Uani d . 1 1 . . H H5' 1.3379 -0.2134 1.0265 0.089 Uiso calc R 1 1 . . C C6' 1.1544(4) -0.15597(19) 1.04293(17) 0.0624(8) Uani d . 1 1 . . H H6' 1.1236 -0.1613 0.9940 0.075 Uiso calc R 1 1 . . N N1 1.0397(4) -0.0685(2) 1.21841(14) 0.0858(10) Uani d . 1 1 . . H H1A 1.0716 -0.0636 1.2631 0.103 Uiso calc R 1 1 . . H H1B 0.9588 -0.0473 1.2070 0.103 Uiso calc R 1 1 . . N N2 0.7503(2) -0.03157(13) 0.82988(10) 0.0461(5) Uani d . 1 1 . . O O1 0.8590(3) -0.04165(18) 1.11148(11) 0.0792(7) Uani d . 1 1 . . O O2 0.9070(2) -0.09711(12) 1.00172(10) 0.0533(5) Uani d . 1 1 . . O O3 0.64582(19) 0.19706(12) 0.99729(9) 0.0492(4) Uani d . 1 1 . . H H3 0.7146 0.2082 1.0234 0.074 Uiso calc R 1 1 . . O O4 0.8988(2) 0.22811(12) 0.97916(9) 0.0493(5) Uani d . 1 1 . . H H4 0.9790 0.2463 0.9721 0.074 Uiso calc R 1 1 . . O O5 1.05780(19) 0.20907(13) 0.86056(11) 0.0567(5) Uani d . 1 1 . . H H5A 1.0672 0.2605 0.8540 0.085 Uiso calc R 1 1 . . O O6 0.8938(2) 0.36055(12) 0.86885(12) 0.0613(5) Uani d . 1 1 . . O O7 0.7770(13) 0.3303(12) 0.7134(9) 0.092(3) Uani d PU 0.578(12) 1 B 1 O O7' 0.7307(16) 0.3306(16) 0.7166(13) 0.084(3) Uani d PU 0.422(12) 1 B 2 O O8 0.45273(18) 0.06771(13) 0.88177(10) 0.0525(5) Uani d . 1 1 . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_12 _atom_site_aniso_U_13 _atom_site_aniso_U_23 C1 0.0340(14) 0.0631(16) 0.0404(12) -0.0009(13) 0.0003(11) -0.0027(11) C2 0.0407(16) 0.0666(18) 0.0650(17) -0.0101(15) 0.0019(13) 0.0052(14) C3 0.0552(19) 0.0600(16) 0.0609(17) -0.0055(15) 0.0027(15) 0.0118(13) C4 0.0425(15) 0.0532(15) 0.0457(14) 0.0050(13) -0.0030(11) 0.0054(11) C5 0.0368(14) 0.0518(14) 0.0365(12) 0.0057(12) -0.0025(10) 0.0001(10) C6 0.0378(14) 0.0488(14) 0.0506(14) 0.0084(12) -0.0013(12) 0.0003(11) C7 0.0367(14) 0.0537(14) 0.0424(13) 0.0037(12) 0.0040(11) -0.0013(11) C8 0.0348(14) 0.0524(14) 0.0462(13) -0.0005(12) 0.0019(11) 0.0017(11) C9 0.0351(13) 0.0507(13) 0.0390(12) 0.0015(12) -0.0043(10) -0.0035(10) C10 0.0356(14) 0.0515(14) 0.0344(12) 0.0059(11) -0.0004(10) -0.0047(10) C11 0.0297(13) 0.0502(13) 0.0399(12) -0.0002(11) 0.0002(10) -0.0014(10) C12 0.0364(14) 0.0590(16) 0.0535(15) 0.0064(13) -0.0080(12) -0.0011(12) C13 0.0502(17) 0.0558(15) 0.0522(15) 0.0080(14) -0.0063(13) 0.0050(11) C14 0.0480(16) 0.0524(15) 0.0532(15) 0.0039(13) -0.0008(13) -0.0009(12) C15 0.0641(19) 0.0610(16) 0.0442(14) -0.0007(15) 0.0094(13) 0.0038(12) C16 0.069(2) 0.0665(18) 0.0457(14) 0.0031(16) -0.0044(14) 0.0074(13) C17 0.0373(14) 0.0496(14) 0.0376(12) 0.0042(12) -0.0020(10) 0.0008(10) C18 0.0553(17) 0.0493(14) 0.0499(14) 0.0053(13) 0.0003(13) -0.0020(11) C19 0.0615(19) 0.0633(17) 0.0420(14) 0.0028(16) -0.0019(14) 0.0099(12) C20 0.0339(16) 0.106(3) 0.082(2) 0.0081(18) 0.0051(15) -0.0039(19) C21 0.101(3) 0.0491(16) 0.092(2) 0.0004(19) 0.003(2) 0.0063(16) C22 0.135(6) 0.138(6) 0.067(4) 0.031(5) 0.013(4) 0.034(4) C22' 0.097(6) 0.126(6) 0.088(6) 0.041(5) 0.003(5) 0.037(5) C23 0.072(2) 0.0711(19) 0.0441(14) 0.0178(17) -0.0071(14) -0.0102(13) C24 0.149(4) 0.077(2) 0.072(2) 0.017(3) -0.021(3) -0.0308(19) C1' 0.0545(17) 0.0534(15) 0.0496(14) -0.0008(14) -0.0054(13) 0.0126(12) C2' 0.067(2) 0.0612(17) 0.0519(16) -0.0053(16) -0.0100(15) 0.0187(13) C3' 0.080(3) 0.069(2) 0.071(2) -0.004(2) -0.031(2) 0.0131(17) C4' 0.069(2) 0.0639(19) 0.103(3) 0.0035(19) -0.032(2) 0.0146(19) C5' 0.061(2) 0.069(2) 0.091(2) 0.0112(18) -0.0127(18) 0.0022(17) C6' 0.064(2) 0.0612(17) 0.0618(18) 0.0054(17) -0.0093(16) 0.0075(14) N1 0.089(2) 0.125(3) 0.0431(13) 0.005(2) -0.0066(14) 0.0039(15) N2 0.0471(13) 0.0501(12) 0.0412(11) 0.0055(11) -0.0047(10) -0.0058(8) O1 0.0785(16) 0.1133(18) 0.0457(11) 0.0293(15) -0.0017(11) -0.0006(11) O2 0.0560(12) 0.0576(11) 0.0462(10) 0.0098(9) -0.0034(9) 0.0067(8) O3 0.0427(11) 0.0645(11) 0.0404(9) 0.0048(9) 0.0031(8) -0.0097(8) O4 0.0418(11) 0.0626(11) 0.0436(9) -0.0016(9) -0.0073(8) -0.0034(8) O5 0.0392(11) 0.0613(11) 0.0695(12) -0.0060(9) 0.0066(9) 0.0040(10) O6 0.0618(13) 0.0485(10) 0.0737(13) -0.0011(10) 0.0018(10) 0.0024(9) O7 0.104(6) 0.104(3) 0.069(3) 0.011(6) -0.007(5) 0.047(3) O7' 0.087(7) 0.096(4) 0.067(4) 0.013(6) 0.001(6) 0.036(3) O8 0.0320(10) 0.0767(12) 0.0488(10) 0.0033(9) -0.0025(8) -0.0018(9) _geom_special_details ; All e.s.d.'s (except the e.s.d. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell e.s.d.'s are taken into account individually in the estimation of e.s.d.'s in distances, angles and torsion angles; correlations between e.s.d.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell e.s.d.'s is used for estimating e.s.d.'s involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_site_symmetry_2 _geom_bond_distance _geom_bond_publ_flag C1 O8 . 1.437(3) ? C1 C2 . 1.525(4) ? C1 C11 . 1.551(3) ? C1 H1 . 1.0000 ? C2 C3 . 1.523(4) ? C2 H2A . 0.9900 ? C2 H2B . 0.9900 ? C3 C4 . 1.515(4) ? C3 H3A . 0.9900 ? C3 H3B . 0.9900 ? C4 O2 . 1.479(3) ? C4 C5 . 1.537(4) ? C4 C18 . 1.540(4) ? C5 C6 . 1.542(4) ? C5 C11 . 1.563(3) ? C5 H5 . 1.0000 ? C6 C7 . 1.543(3) ? C6 H6A . 0.9900 ? C6 H6B . 0.9900 ? C7 C8 . 1.528(4) ? C7 C17 . 1.549(4) ? C7 H7 . 1.0000 ? C8 O5 . 1.440(3) ? C8 C15 . 1.552(4) ? C8 C9 . 1.570(4) ? C9 O4 . 1.419(3) ? C9 C14 . 1.525(4) ? C9 C10 . 1.542(4) ? C10 O3 . 1.442(3) ? C10 C12 . 1.558(3) ? C10 C11 . 1.574(4) ? C11 C17 . 1.538(3) ? C12 C13 . 1.540(4) ? C12 H12A . 0.9900 ? C12 H12B . 0.9900 ? C13 C16 . 1.520(4) ? C13 C14 . 1.525(4) ? C13 H13 . 1.0000 ? C14 O6 . 1.418(4) ? C14 H14 . 1.0000 ? C15 C16 . 1.518(5) ? C15 H15A . 0.9900 ? C15 H15B . 0.9900 ? C16 O7' . 1.40(2) ? C16 O7 . 1.487(17) ? C16 H16 . 1.0000 ? C17 N2 . 1.467(3) ? C17 H17 . 1.0000 ? C18 N2 . 1.465(3) ? C18 H18A . 0.9900 ? C18 H18B . 0.9900 ? C19 O1 . 1.223(4) ? C19 O2 . 1.348(3) ? C19 C1' . 1.456(4) ? C20 O8 . 1.416(3) ? C20 H20A . 0.9800 ? C20 H20B . 0.9800 ? C20 H20C . 0.9800 ? C21 O6 . 1.431(4) ? C21 H21A . 0.9800 ? C21 H21B . 0.9800 ? C21 H21C . 0.9800 ? C22 O7 . 1.350(19) ? C22 H22A . 0.9800 ? C22 H22B . 0.9800 ? C22 H22C . 0.9800 ? C22' O7' . 1.09(2) ? C22' H22D . 0.9800 ? C22' H22E . 0.9800 ? C22' H22F . 0.9800 ? C23 N2 . 1.465(3) ? C23 C24 . 1.497(5) ? C23 H23A . 0.9900 ? C23 H23B . 0.9900 ? C24 H24A . 0.9800 ? C24 H24B . 0.9800 ? C24 H24C . 0.9800 ? C1' C6' . 1.402(4) ? C1' C2' . 1.423(4) ? C2' N1 . 1.353(4) ? C2' C3' . 1.404(5) ? C3' C4' . 1.352(5) ? C3' H3' . 0.9500 ? C4' C5' . 1.397(5) ? C4' H4' . 0.9500 ? C5' C6' . 1.371(5) ? C5' H5' . 0.9500 ? C6' H6' . 0.9500 ? N1 H1A . 0.8800 ? N1 H1B . 0.8800 ? O3 H3 . 0.8400 ? O4 H4 . 0.8400 ? O5 H5A . 0.8400 ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle _geom_angle_publ_flag O8 C1 C2 . . 107.4(2) ? O8 C1 C11 . . 111.0(2) ? C2 C1 C11 . . 117.0(2) ? O8 C1 H1 . . 107.0 ? C2 C1 H1 . . 107.0 ? C11 C1 H1 . . 107.0 ? C3 C2 C1 . . 111.5(2) ? C3 C2 H2A . . 109.3 ? C1 C2 H2A . . 109.3 ? C3 C2 H2B . . 109.3 ? C1 C2 H2B . . 109.3 ? H2A C2 H2B . . 108.0 ? C4 C3 C2 . . 107.8(2) ? C4 C3 H3A . . 110.1 ? C2 C3 H3A . . 110.1 ? C4 C3 H3B . . 110.1 ? C2 C3 H3B . . 110.1 ? H3A C3 H3B . . 108.5 ? O2 C4 C3 . . 110.5(2) ? O2 C4 C5 . . 110.1(2) ? C3 C4 C5 . . 112.4(2) ? O2 C4 C18 . . 101.0(2) ? C3 C4 C18 . . 113.2(2) ? C5 C4 C18 . . 109.2(2) ? C4 C5 C6 . . 108.2(2) ? C4 C5 C11 . . 107.1(2) ? C6 C5 C11 . . 106.03(19) ? C4 C5 H5 . . 111.7 ? C6 C5 H5 . . 111.7 ? C11 C5 H5 . . 111.7 ? C5 C6 C7 . . 104.6(2) ? C5 C6 H6A . . 110.8 ? C7 C6 H6A . . 110.8 ? C5 C6 H6B . . 110.8 ? C7 C6 H6B . . 110.8 ? H6A C6 H6B . . 108.9 ? C8 C7 C6 . . 110.8(2) ? C8 C7 C17 . . 111.3(2) ? C6 C7 C17 . . 103.5(2) ? C8 C7 H7 . . 110.4 ? C6 C7 H7 . . 110.4 ? C17 C7 H7 . . 110.4 ? O5 C8 C7 . . 106.0(2) ? O5 C8 C15 . . 107.5(2) ? C7 C8 C15 . . 111.7(2) ? O5 C8 C9 . . 108.5(2) ? C7 C8 C9 . . 109.8(2) ? C15 C8 C9 . . 113.1(2) ? O4 C9 C14 . . 110.7(2) ? O4 C9 C10 . . 107.86(19) ? C14 C9 C10 . . 103.6(2) ? O4 C9 C8 . . 112.5(2) ? C14 C9 C8 . . 109.5(2) ? C10 C9 C8 . . 112.3(2) ? O3 C10 C9 . . 106.68(19) ? O3 C10 C12 . . 107.6(2) ? C9 C10 C12 . . 102.42(19) ? O3 C10 C11 . . 107.93(19) ? C9 C10 C11 . . 117.1(2) ? C12 C10 C11 . . 114.4(2) ? C17 C11 C1 . . 119.2(2) ? C17 C11 C5 . . 97.83(19) ? C1 C11 C5 . . 111.34(19) ? C17 C11 C10 . . 107.79(19) ? C1 C11 C10 . . 108.1(2) ? C5 C11 C10 . . 112.4(2) ? C13 C12 C10 . . 107.7(2) ? C13 C12 H12A . . 110.2 ? C10 C12 H12A . . 110.2 ? C13 C12 H12B . . 110.2 ? C10 C12 H12B . . 110.2 ? H12A C12 H12B . . 108.5 ? C16 C13 C14 . . 111.9(3) ? C16 C13 C12 . . 110.8(2) ? C14 C13 C12 . . 101.2(2) ? C16 C13 H13 . . 110.9 ? C14 C13 H13 . . 110.9 ? C12 C13 H13 . . 110.9 ? O6 C14 C13 . . 118.6(2) ? O6 C14 C9 . . 109.4(2) ? C13 C14 C9 . . 101.4(2) ? O6 C14 H14 . . 109.0 ? C13 C14 H14 . . 109.0 ? C9 C14 H14 . . 109.0 ? C16 C15 C8 . . 119.7(2) ? C16 C15 H15A . . 107.4 ? C8 C15 H15A . . 107.4 ? C16 C15 H15B . . 107.4 ? C8 C15 H15B . . 107.4 ? H15A C15 H15B . . 106.9 ? O7' C16 C15 . . 117.7(7) ? O7 C16 C15 . . 100.0(5) ? O7' C16 C13 . . 103.4(9) ? O7 C16 C13 . . 112.2(7) ? C15 C16 C13 . . 113.8(2) ? O7' C16 H16 . . 100.7 ? O7 C16 H16 . . 110.1 ? C15 C16 H16 . . 110.1 ? C13 C16 H16 . . 110.1 ? N2 C17 C11 . . 109.6(2) ? N2 C17 C7 . . 115.4(2) ? C11 C17 C7 . . 101.48(18) ? N2 C17 H17 . . 110.0 ? C11 C17 H17 . . 110.0 ? C7 C17 H17 . . 110.0 ? N2 C18 C4 . . 114.3(2) ? N2 C18 H18A . . 108.7 ? C4 C18 H18A . . 108.7 ? N2 C18 H18B . . 108.7 ? C4 C18 H18B . . 108.7 ? H18A C18 H18B . . 107.6 ? O1 C19 O2 . . 122.1(3) ? O1 C19 C1' . . 125.5(3) ? O2 C19 C1' . . 112.4(3) ? O8 C20 H20A . . 109.5 ? O8 C20 H20B . . 109.5 ? H20A C20 H20B . . 109.5 ? O8 C20 H20C . . 109.5 ? H20A C20 H20C . . 109.5 ? H20B C20 H20C . . 109.5 ? O6 C21 H21A . . 109.5 ? O6 C21 H21B . . 109.5 ? H21A C21 H21B . . 109.5 ? O6 C21 H21C . . 109.5 ? H21A C21 H21C . . 109.5 ? H21B C21 H21C . . 109.5 ? O7' C22' H22D . . 109.5 ? O7' C22' H22E . . 109.5 ? H22D C22' H22E . . 109.5 ? O7' C22' H22F . . 109.5 ? H22D C22' H22F . . 109.5 ? H22E C22' H22F . . 109.5 ? N2 C23 C24 . . 112.3(3) ? N2 C23 H23A . . 109.1 ? C24 C23 H23A . . 109.1 ? N2 C23 H23B . . 109.1 ? C24 C23 H23B . . 109.1 ? H23A C23 H23B . . 107.9 ? C23 C24 H24A . . 109.5 ? C23 C24 H24B . . 109.5 ? H24A C24 H24B . . 109.5 ? C23 C24 H24C . . 109.5 ? H24A C24 H24C . . 109.5 ? H24B C24 H24C . . 109.5 ? C6' C1' C2' . . 119.1(3) ? C6' C1' C19 . . 120.6(3) ? C2' C1' C19 . . 120.3(3) ? N1 C2' C3' . . 120.7(3) ? N1 C2' C1' . . 121.8(3) ? C3' C2' C1' . . 117.4(3) ? C4' C3' C2' . . 122.2(3) ? C4' C3' H3' . . 118.9 ? C2' C3' H3' . . 118.9 ? C3' C4' C5' . . 120.8(3) ? C3' C4' H4' . . 119.6 ? C5' C4' H4' . . 119.6 ? C6' C5' C4' . . 118.8(3) ? C6' C5' H5' . . 120.6 ? C4' C5' H5' . . 120.6 ? C5' C6' C1' . . 121.7(3) ? C5' C6' H6' . . 119.2 ? C1' C6' H6' . . 119.2 ? C2' N1 H1A . . 120.0 ? C2' N1 H1B . . 120.0 ? H1A N1 H1B . . 120.0 ? C18 N2 C23 . . 110.7(2) ? C18 N2 C17 . . 115.3(2) ? C23 N2 C17 . . 113.2(2) ? C19 O2 C4 . . 121.5(2) ? C10 O3 H3 . . 109.5 ? C9 O4 H4 . . 109.5 ? C8 O5 H5A . . 109.5 ? C14 O6 C21 . . 113.5(3) ? C22 O7 C16 . . 110.3(13) ? C22' O7' C16 . . 142(2) ? C20 O8 C1 . . 113.5(2) ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion _geom_torsion_publ_flag O8 C1 C2 C3 . . . . 172.1(2) ? C11 C1 C2 C3 . . . . 46.5(3) ? C1 C2 C3 C4 . . . . -54.4(3) ? C2 C3 C4 O2 . . . . -170.1(2) ? C2 C3 C4 C5 . . . . 66.6(3) ? C2 C3 C4 C18 . . . . -57.7(3) ? O2 C4 C5 C6 . . . . 58.3(2) ? C3 C4 C5 C6 . . . . -178.2(2) ? C18 C4 C5 C6 . . . . -51.7(3) ? O2 C4 C5 C11 . . . . 172.24(18) ? C3 C4 C5 C11 . . . . -64.2(3) ? C18 C4 C5 C11 . . . . 62.2(3) ? C4 C5 C6 C7 . . . . 100.5(2) ? C11 C5 C6 C7 . . . . -14.2(3) ? C5 C6 C7 C8 . . . . 101.8(2) ? C5 C6 C7 C17 . . . . -17.6(2) ? C6 C7 C8 O5 . . . . 64.6(3) ? C17 C7 C8 O5 . . . . 179.14(19) ? C6 C7 C8 C15 . . . . -178.7(2) ? C17 C7 C8 C15 . . . . -64.1(3) ? C6 C7 C8 C9 . . . . -52.4(3) ? C17 C7 C8 C9 . . . . 62.2(3) ? O5 C8 C9 O4 . . . . -33.9(3) ? C7 C8 C9 O4 . . . . 81.5(3) ? C15 C8 C9 O4 . . . . -153.0(2) ? O5 C8 C9 C14 . . . . 89.7(2) ? C7 C8 C9 C14 . . . . -155.0(2) ? C15 C8 C9 C14 . . . . -29.4(3) ? O5 C8 C9 C10 . . . . -155.8(2) ? C7 C8 C9 C10 . . . . -40.4(3) ? C15 C8 C9 C10 . . . . 85.1(3) ? O4 C9 C10 O3 . . . . 34.5(3) ? C14 C9 C10 O3 . . . . -82.8(2) ? C8 C9 C10 O3 . . . . 159.04(19) ? O4 C9 C10 C12 . . . . 147.5(2) ? C14 C9 C10 C12 . . . . 30.1(2) ? C8 C9 C10 C12 . . . . -88.0(2) ? O4 C9 C10 C11 . . . . -86.4(2) ? C14 C9 C10 C11 . . . . 156.2(2) ? C8 C9 C10 C11 . . . . 38.1(3) ? O8 C1 C11 C17 . . . . -55.8(3) ? C2 C1 C11 C17 . . . . 68.0(3) ? O8 C1 C11 C5 . . . . -168.5(2) ? C2 C1 C11 C5 . . . . -44.7(3) ? O8 C1 C11 C10 . . . . 67.6(3) ? C2 C1 C11 C10 . . . . -168.6(2) ? C4 C5 C11 C17 . . . . -75.3(2) ? C6 C5 C11 C17 . . . . 40.1(2) ? C4 C5 C11 C1 . . . . 50.3(3) ? C6 C5 C11 C1 . . . . 165.7(2) ? C4 C5 C11 C10 . . . . 171.7(2) ? C6 C5 C11 C10 . . . . -72.9(2) ? O3 C10 C11 C17 . . . . -173.14(18) ? C9 C10 C11 C17 . . . . -52.8(3) ? C12 C10 C11 C17 . . . . 67.1(3) ? O3 C10 C11 C1 . . . . 56.8(2) ? C9 C10 C11 C1 . . . . 177.13(19) ? C12 C10 C11 C1 . . . . -63.0(2) ? O3 C10 C11 C5 . . . . -66.5(2) ? C9 C10 C11 C5 . . . . 53.9(3) ? C12 C10 C11 C5 . . . . 173.8(2) ? O3 C10 C12 C13 . . . . 110.3(2) ? C9 C10 C12 C13 . . . . -1.9(2) ? C11 C10 C12 C13 . . . . -129.7(2) ? C10 C12 C13 C16 . . . . 92.0(3) ? C10 C12 C13 C14 . . . . -26.7(3) ? C16 C13 C14 O6 . . . . 46.8(3) ? C12 C13 C14 O6 . . . . 164.9(2) ? C16 C13 C14 C9 . . . . -72.9(3) ? C12 C13 C14 C9 . . . . 45.1(3) ? O4 C9 C14 O6 . . . . 70.7(3) ? C10 C9 C14 O6 . . . . -173.9(2) ? C8 C9 C14 O6 . . . . -53.9(3) ? O4 C9 C14 C13 . . . . -163.2(2) ? C10 C9 C14 C13 . . . . -47.9(2) ? C8 C9 C14 C13 . . . . 72.2(3) ? O5 C8 C15 C16 . . . . -136.5(3) ? C7 C8 C15 C16 . . . . 107.7(3) ? C9 C8 C15 C16 . . . . -16.8(4) ? C8 C15 C16 O7' . . . . 139.0(12) ? C8 C15 C16 O7 . . . . 137.6(8) ? C8 C15 C16 C13 . . . . 17.7(4) ? C14 C13 C16 O7' . . . . -100.8(8) ? C12 C13 C16 O7' . . . . 147.2(8) ? C14 C13 C16 O7 . . . . -84.6(6) ? C12 C13 C16 O7 . . . . 163.3(6) ? C14 C13 C16 C15 . . . . 28.1(3) ? C12 C13 C16 C15 . . . . -83.9(3) ? C1 C11 C17 N2 . . . . -48.0(3) ? C5 C11 C17 N2 . . . . 71.9(2) ? C10 C11 C17 N2 . . . . -171.5(2) ? C1 C11 C17 C7 . . . . -170.4(2) ? C5 C11 C17 C7 . . . . -50.5(2) ? C10 C11 C17 C7 . . . . 66.1(2) ? C8 C7 C17 N2 . . . . 166.20(19) ? C6 C7 C17 N2 . . . . -74.8(2) ? C8 C7 C17 C11 . . . . -75.4(2) ? C6 C7 C17 C11 . . . . 43.5(2) ? O2 C4 C18 N2 . . . . -157.5(2) ? C3 C4 C18 N2 . . . . 84.4(3) ? C5 C4 C18 N2 . . . . -41.5(3) ? O1 C19 C1' C6' . . . . -176.2(3) ? O2 C19 C1' C6' . . . . 4.5(4) ? O1 C19 C1' C2' . . . . 2.0(5) ? O2 C19 C1' C2' . . . . -177.3(3) ? C6' C1' C2' N1 . . . . 177.9(3) ? C19 C1' C2' N1 . . . . -0.3(5) ? C6' C1' C2' C3' . . . . -0.7(4) ? C19 C1' C2' C3' . . . . -178.9(3) ? N1 C2' C3' C4' . . . . -177.7(3) ? C1' C2' C3' C4' . . . . 0.9(5) ? C2' C3' C4' C5' . . . . -0.2(5) ? C3' C4' C5' C6' . . . . -0.8(5) ? C4' C5' C6' C1' . . . . 0.9(5) ? C2' C1' C6' C5' . . . . -0.2(5) ? C19 C1' C6' C5' . . . . 178.0(3) ? C4 C18 N2 C23 . . . . 169.7(2) ? C4 C18 N2 C17 . . . . 39.6(3) ? C24 C23 N2 C18 . . . . 79.2(3) ? C24 C23 N2 C17 . . . . -149.5(3) ? C11 C17 N2 C18 . . . . -57.3(3) ? C7 C17 N2 C18 . . . . 56.4(3) ? C11 C17 N2 C23 . . . . 173.8(2) ? C7 C17 N2 C23 . . . . -72.5(3) ? O1 C19 O2 C4 . . . . 11.8(4) ? C1' C19 O2 C4 . . . . -168.9(2) ? C3 C4 O2 C19 . . . . -67.1(3) ? C5 C4 O2 C19 . . . . 57.5(3) ? C18 C4 O2 C19 . . . . 172.8(2) ? C13 C14 O6 C21 . . . . 74.1(3) ? C9 C14 O6 C21 . . . . -170.5(2) ? O7' C16 O7 C22 . . . . -78(5) ? C15 C16 O7 C22 . . . . 98.3(9) ? C13 C16 O7 C22 . . . . -140.7(8) ? O7 C16 O7' C22' . . . . 135(8) ? C15 C16 O7' C22' . . . . 130(3) ? C13 C16 O7' C22' . . . . -103(3) ? C2 C1 O8 C20 . . . . 83.5(3) ? C11 C1 O8 C20 . . . . -147.4(3) ? loop_ _geom_hbond_atom_site_label_D _geom_hbond_atom_site_label_H _geom_hbond_atom_site_label_A _geom_hbond_site_symmetry_A _geom_hbond_distance_DH _geom_hbond_distance_HA _geom_hbond_distance_DA _geom_hbond_angle_DHA O5 H5A O6 . 0.84 2.34 2.909(3) 125.5 O4 H4 O5 . 0.84 2.27 2.684(3) 111.1 O4 H4 O3 3_557 0.84 1.94 2.713(3) 152.9 O3 H3 O4 . 0.84 1.99 2.524(3) 121.0 N1 H1B O1 . 0.88 2.00 2.666(4) 131.0 N1 H1A O8 2_655 0.88 2.19 2.999(3) 152.4 data_New_Global_Publ_Block _journal_date_recd_electronic 2015-06-20 _journal_date_accepted 2015-06-30 _journal_name_full 'Acta Crystallographica, Section E' _journal_year 2015 _journal_volume 71 _journal_issue 8 _journal_page_first o550 _journal_page_last o551 _journal_paper_category HO _journal_paper_doi 10.1107/S205698901501258X _journal_coeditor_code HG5447 _publ_contact_author_name 'Xin-Wei Shi' _publ_contact_author_address ; Xi'an Botanical Garden, Institute of Botany of Shaanxi Province, Xi'an 710061, People's Republic of China ; _publ_contact_author_email 'sxw@ms.xab.ac.cn' _publ_contact_author_fax '0086 029 85251800' _publ_contact_author_phone '0086 029 85251800' _publ_section_title ; Crystal structure of sepaconitine, a C~19~-diterpenoid alkaloid from the roots of Aconitum sinomontanum Nakai ; loop_ _publ_author_name _publ_author_footnote _publ_author_address 'Shi, Xin-Wei' . ; Xi'an Botanical Garden, Institute of Botany of Shaanxi Province, Xi'an 710061, People's Republic of China ; 'Lu, Qiang-Qiang' . ; Xi'an Botanical Garden, Institute of Botany of Shaanxi Province, Xi'an 710061, People's Republic of China ; 'Zhou, Jun-Hui' . ; Xi'an Botanical Garden, Institute of Botany of Shaanxi Province, Xi'an 710061, People's Republic of China ; 'Cui, Xin-Ai' . ; Xi'an Botanical Garden, Institute of Botany of Shaanxi Province, Xi'an 710061, People's Republic of China ; _publ_section_synopsis . _shelx_res_file ; TITL x5 in P2(1)2(1)2(1) CELL 1.54178 9.6917 16.0510 18.3549 90.000 90.000 90.000 ZERR 4.00 0.0005 0.0007 0.0007 0.000 0.000 0.000 LATT -1 SYMM 0.50000-X,-Y, 0.50000+Z SYMM 0.50000+X, 0.50000-Y,-Z SYMM -X, 0.50000+Y, 0.50000-Z SFAC C H N O UNIT 120 168 8 32 MERG 2 OMIT 0 130 L.S. 4 ACTA bond $h FMAP 2 PLAN 25 HTAB O5 O6 HTAB O4 O5 HTAB O4 O3_$5 HTAB O3 O4 HTAB N1 O1 HTAB N1 O8_$4 HTAB C23 O1_$3 HTAB C20 O5_$2 HTAB C12 O4_$1 HTAB C12 O8 HTAB C5 O1 HTAB C3 O1 HTAB C2 N2 htab 2 conf size .32 .32 .28 HTAB C2 N2 HTAB C3 O1 HTAB C5 O1 HTAB C12 O8 EQIV $1 x-1/2, -y+1/2, -z+2 HTAB C12 O4_$1 EQIV $2 x-1, y, z HTAB C20 O5_$2 EQIV $3 -x+3/2, -y, z-1/2 HTAB C23 O1_$3 EQIV $4 -x+3/2, -y, z+1/2 HTAB N1 O8_$4 HTAB N1 O1 HTAB O3 O4 EQIV $5 x+1/2, -y+1/2, -z+2 HTAB O4 O3_$5 HTAB O5 O6 HTAB C2 N2 HTAB C3 O1 HTAB C5 O1 HTAB C12 O8 HTAB C12 O4_$1 HTAB C20 O5_$2 HTAB C23 O1_$3 HTAB N1 O8_$4 HTAB N1 O1 HTAB O3 O4 HTAB O4 O3_$5 HTAB O4 O5 HTAB O5 O6 HTAB C2 N2 HTAB C3 O1 HTAB C5 O1 HTAB C12 O8 HTAB C12 O4_$1 HTAB C20 O5_$2 HTAB C23 O1_$3 HTAB N1 O8_$4 HTAB N1 O1 HTAB O3 O4 HTAB O4 O3_$5 HTAB O4 O5 HTAB O5 O6 SIMU 0.01 O7 C22 O7' C22' ISOR 0.01 O7 O7' C22 C22' WGHT 0.075200 0.041100 FVAR 0.141710 0.577820 temp -100 C1 1 0.551898 0.044405 0.936269 11.000000 0.034040 = 0.063150 0.040410 -0.002680 0.000300 -0.000860 AFIX 13 H1 2 0.522384 0.071305 0.982874 11.000000 -1.200000 AFIX 0 C2 1 0.540082 -0.049521 0.947288 11.000000 0.040710 = 0.066580 0.064960 0.005150 0.001940 -0.010090 AFIX 23 H2A 2 0.449408 -0.062637 0.969318 11.000000 -1.200000 H2B 2 0.545061 -0.077750 0.899404 11.000000 -1.200000 AFIX 0 C3 1 0.654524 -0.082416 0.996379 11.000000 0.055170 = 0.060000 0.060930 0.011820 0.002690 -0.005540 AFIX 23 H3A 2 0.643963 -0.059795 1.046246 11.000000 -1.200000 H3B 2 0.650277 -0.143968 0.999009 11.000000 -1.200000 AFIX 0 C4 1 0.791184 -0.055070 0.964208 11.000000 0.042540 = 0.053200 0.045730 0.005360 -0.003010 0.004960 C5 1 0.810553 0.039912 0.967175 11.000000 0.036820 = 0.051760 0.036470 0.000140 -0.002530 0.005740 AFIX 13 H5 2 0.805378 0.061451 1.018224 11.000000 -1.200000 AFIX 0 C6 1 0.949710 0.061341 0.931024 11.000000 0.037780 = 0.048760 0.050570 0.000260 -0.001310 0.008410 AFIX 23 H6A 2 1.010118 0.011672 0.928748 11.000000 -1.200000 H6B 2 0.997895 0.105869 0.958329 11.000000 -1.200000 AFIX 0 C7 1 0.910863 0.091218 0.853793 11.000000 0.036700 = 0.053690 0.042410 -0.001310 0.003990 0.003730 AFIX 13 H7 2 0.973980 0.065916 0.816807 11.000000 -1.200000 AFIX 0 C8 1 0.915713 0.186217 0.849097 11.000000 0.034800 = 0.052400 0.046210 0.001740 0.001870 -0.000490 C9 1 0.826722 0.225076 0.911952 11.000000 0.035130 = 0.050690 0.038980 -0.003490 -0.004330 0.001470 C10 1 0.691090 0.177029 0.924563 11.000000 0.035590 = 0.051530 0.034380 -0.004710 -0.000400 0.005920 C11 1 0.696811 0.079341 0.917614 11.000000 0.029730 = 0.050170 0.039920 -0.001420 0.000160 -0.000230 C12 1 0.590406 0.220274 0.870229 11.000000 0.036370 = 0.059000 0.053510 -0.001110 -0.007980 0.006440 AFIX 23 H12A 2 0.556836 0.179595 0.833767 11.000000 -1.200000 H12B 2 0.509838 0.243103 0.896703 11.000000 -1.200000 AFIX 0 C13 1 0.669987 0.291001 0.832221 11.000000 0.050160 = 0.055780 0.052180 0.004980 -0.006280 0.008010 AFIX 13 H13 2 0.608420 0.339860 0.822950 11.000000 -1.200000 AFIX 0 C14 1 0.778317 0.311839 0.889646 11.000000 0.048010 = 0.052420 0.053170 -0.000880 -0.000840 0.003900 AFIX 13 H14 2 0.731945 0.338909 0.932170 11.000000 -1.200000 AFIX 0 C15 1 0.873676 0.217932 0.772381 11.000000 0.064150 = 0.061040 0.044200 0.003770 0.009370 -0.000700 AFIX 23 H15A 2 0.945889 0.257350 0.756039 11.000000 -1.200000 H15B 2 0.876699 0.169630 0.738877 11.000000 -1.200000 AFIX 0 C16 1 0.735183 0.260458 0.761827 11.000000 0.069090 = 0.066520 0.045660 0.007410 -0.004440 0.003150 AFIX 13 H16 2 0.670202 0.222464 0.735614 11.000000 -1.200000 AFIX 0 C17 1 0.761951 0.058234 0.843477 11.000000 0.037250 = 0.049580 0.037620 0.000790 -0.001990 0.004240 AFIX 13 H17 2 0.714563 0.090027 0.803865 11.000000 -1.200000 AFIX 0 C18 1 0.812726 -0.085264 0.885360 11.000000 0.055270 = 0.049320 0.049930 -0.002010 0.000320 0.005340 AFIX 23 H18A 2 0.913036 -0.089257 0.875788 11.000000 -1.200000 H18B 2 0.773439 -0.141935 0.880581 11.000000 -1.200000 AFIX 0 C19 1 0.937108 -0.080984 1.072018 11.000000 0.061480 = 0.063330 0.042010 0.009890 -0.001910 0.002850 C20 1 0.318220 0.080024 0.909907 11.000000 0.033910 = 0.106050 0.081580 -0.003850 0.005100 0.008100 AFIX 137 H20A 2 0.283931 0.027648 0.930525 11.000000 -1.500000 H20B 2 0.256701 0.098214 0.870632 11.000000 -1.500000 H20C 2 0.320939 0.122728 0.948039 11.000000 -1.500000 AFIX 0 C21 1 0.861884 0.446782 0.858305 11.000000 0.100980 = 0.049090 0.092140 0.006320 0.002950 0.000400 AFIX 137 H21A 2 0.807972 0.453381 0.813505 11.000000 -1.500000 H21B 2 0.947667 0.478787 0.854340 11.000000 -1.500000 H21C 2 0.808134 0.467212 0.899850 11.000000 -1.500000 PART 1 AFIX 0 C22 1 0.749864 0.311324 0.643230 21.000000 0.135360 = 0.138450 0.066990 0.034030 0.012520 0.031380 AFIX 137 H22A 2 0.816202 0.269654 0.626030 21.000000 -1.500000 H22B 2 0.757523 0.361715 0.613355 21.000000 -1.500000 H22C 2 0.656139 0.288844 0.639342 21.000000 -1.500000 PART 2 AFIX 0 C22' 1 0.674288 0.357315 0.670690 -21.000000 0.096710 = 0.126060 0.087990 0.037100 0.002750 0.040650 AFIX 137 H22D 2 0.638591 0.312378 0.639849 -21.000000 -1.500000 H22E 2 0.736410 0.392663 0.642068 -21.000000 -1.500000 H22F 2 0.597239 0.390880 0.688966 -21.000000 -1.500000 PART 0 AFIX 0 C23 1 0.796355 -0.055871 0.756900 11.000000 0.072210 = 0.071070 0.044120 -0.010170 -0.007110 0.017760 AFIX 23 H23A 2 0.896366 -0.068318 0.758323 11.000000 -1.200000 H23B 2 0.782209 -0.008621 0.723046 11.000000 -1.200000 AFIX 0 C24 1 0.720629 -0.130460 0.728696 11.000000 0.148880 = 0.077280 0.072000 -0.030800 -0.021130 0.017010 AFIX 137 H24A 2 0.751610 -0.180298 0.754843 11.000000 -1.500000 H24B 2 0.739376 -0.137056 0.676548 11.000000 -1.500000 H24C 2 0.621316 -0.122867 0.736229 11.000000 -1.500000 AFIX 0 C1' 1 1.069157 -0.116185 1.093961 11.000000 0.054510 = 0.053430 0.049630 0.012650 -0.005440 -0.000830 C2' 1 1.115288 -0.108490 1.167241 11.000000 0.066930 = 0.061220 0.051900 0.018730 -0.010030 -0.005350 C3' 1 1.244571 -0.142564 1.184548 11.000000 0.079520 = 0.068690 0.071330 0.013050 -0.030790 -0.004260 AFIX 43 H3' 2 1.276906 -0.138906 1.233303 11.000000 -1.200000 AFIX 0 C4' 1 1.324575 -0.180411 1.134120 11.000000 0.069020 = 0.063900 0.103000 0.014580 -0.031580 0.003530 AFIX 43 H4' 2 1.411596 -0.202547 1.148007 11.000000 -1.200000 AFIX 0 C5' 1 1.280941 -0.187390 1.061862 11.000000 0.061300 = 0.069140 0.091300 0.002170 -0.012680 0.011190 AFIX 43 H5' 2 1.337946 -0.213444 1.026453 11.000000 -1.200000 AFIX 0 C6' 1 1.154364 -0.155970 1.042934 11.000000 0.064070 = 0.061240 0.061750 0.007480 -0.009270 0.005410 AFIX 43 H6' 2 1.123598 -0.161283 0.994013 11.000000 -1.200000 AFIX 0 N1 3 1.039745 -0.068460 1.218412 11.000000 0.089340 = 0.125060 0.043110 0.003920 -0.006640 0.005060 AFIX 93 H1A 2 1.071554 -0.063566 1.263113 11.000000 -1.200000 H1B 2 0.958808 -0.047322 1.206989 11.000000 -1.200000 AFIX 0 N2 3 0.750319 -0.031570 0.829882 11.000000 0.047080 = 0.050110 0.041180 -0.005830 -0.004730 0.005460 O1 4 0.858999 -0.041655 1.111479 11.000000 0.078500 = 0.113310 0.045710 -0.000580 -0.001710 0.029290 O2 4 0.906963 -0.097110 1.001716 11.000000 0.056040 = 0.057550 0.046230 0.006740 -0.003420 0.009790 O3 4 0.645817 0.197056 0.997295 11.000000 0.042670 = 0.064550 0.040350 -0.009670 0.003130 0.004810 AFIX 147 H3 2 0.714629 0.208161 1.023371 11.000000 -1.500000 AFIX 0 O4 4 0.898824 0.228115 0.979160 11.000000 0.041850 = 0.062550 0.043630 -0.003380 -0.007300 -0.001570 AFIX 147 H4 2 0.978969 0.246329 0.972101 11.000000 -1.500000 AFIX 0 O5 4 1.057797 0.209071 0.860555 11.000000 0.039240 = 0.061250 0.069480 0.004000 0.006630 -0.006020 AFIX 147 H5A 2 1.067213 0.260547 0.853971 11.000000 -1.500000 AFIX 0 O6 4 0.893841 0.360551 0.868850 11.000000 0.061800 = 0.048530 0.073680 0.002400 0.001760 -0.001090 PART 1 O7 4 0.777033 0.330275 0.713419 21.000000 0.104100 = 0.104000 0.068830 0.046510 -0.006640 0.010510 PART 2 O7' 4 0.730728 0.330584 0.716608 -21.000000 0.087240 = 0.096490 0.066820 0.035870 0.001140 0.012600 PART 0 O8 4 0.452733 0.067714 0.881766 11.000000 0.032000 = 0.076650 0.048840 -0.001810 -0.002530 0.003280 HKLF 4 END Q1 1 1.001100 0.052500 0.799700 11.000000 0.050000 0.460000 Q2 1 0.632600 -0.202500 0.975600 11.000000 0.050000 0.140000 Q3 1 0.677200 -0.082200 0.621500 11.000000 0.050000 0.130000 Q4 1 0.820300 -0.180600 0.998100 11.000000 0.050000 0.130000 Q5 1 0.244500 0.042800 0.878600 11.000000 0.050000 0.130000 Q6 1 0.690900 0.420500 0.692400 11.000000 0.050000 0.120000 Q7 1 0.678300 0.342300 0.985900 11.000000 0.050000 0.120000 Q8 1 0.673800 0.224400 0.625800 11.000000 0.050000 0.110000 Q9 1 0.822100 -0.207300 0.880800 11.000000 0.050000 0.110000 Q10 1 1.422400 -0.290100 0.976000 11.000000 0.050000 0.110000 Q11 1 0.601100 -0.123100 0.601000 11.000000 0.050000 0.110000 Q12 1 0.295100 0.198200 0.881700 11.000000 0.050000 0.110000 Q13 1 1.395700 -0.275500 1.008600 11.000000 0.050000 0.110000 Q14 1 0.642100 0.456500 0.638700 11.000000 0.050000 0.110000 Q15 1 0.716400 0.440100 0.746800 11.000000 0.050000 0.110000 Q16 1 0.506000 0.284900 0.605500 11.000000 0.050000 0.110000 Q17 1 1.065700 -0.224900 1.132800 11.000000 0.050000 0.110000 Q18 1 0.740600 0.054900 0.943100 11.000000 0.050000 0.100000 Q19 1 0.792600 -0.185700 0.957500 11.000000 0.050000 0.100000 Q20 1 0.680700 0.460600 0.774800 11.000000 0.050000 0.100000 Q21 1 0.756600 0.358100 0.944600 11.000000 0.050000 0.100000 Q22 1 0.776900 0.480000 0.747000 11.000000 0.050000 0.100000 Q23 1 0.019700 0.567400 0.799500 11.000000 0.050000 0.100000 Q24 1 0.912100 0.108000 1.044700 11.000000 0.050000 0.100000 Q25 1 0.643500 0.161400 0.739500 11.000000 0.050000 0.100000 HKLF 4 REM x5 in P2(1)2(1)2(1) REM R1= 0.0461 for 3831 Fo > 4sig(Fo) and 0.0548 for all 4528 data REM 388 parameters refined using 60 restraints ;