data_shelxl _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common Pegaharmine F _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C17 H18 N2 O4' _chemical_formula_weight 314.33 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 7.6922(15) _cell_length_b 7.9904(16) _cell_length_c 24.276(5) _cell_angle_alpha 90.00 _cell_angle_beta 93.51(3) _cell_angle_gamma 90.00 _cell_volume 1489.3(5) _cell_formula_units_Z 4 _cell_measurement_temperature 113(2) _cell_measurement_reflns_used 3650 _cell_measurement_theta_min 1.6809 _cell_measurement_theta_max 27.9103 _exptl_crystal_description 'prism' _exptl_crystal_colour orange-red _exptl_crystal_size_max 0.20 _exptl_crystal_size_mid 0.18 _exptl_crystal_size_min 0.12 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.402 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 664 _exptl_absorpt_coefficient_mu 0.101 _exptl_absorpt_correction_type MULTI-SCAN _exptl_absorpt_correction_T_min 0.9801 _exptl_absorpt_correction_T_max 0.9880 _exptl_absorpt_process_details crystalclear _exptl_special_details ; ? ; _diffrn_ambient_temperature 113(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'rotating anode' _diffrn_radiation_monochromator confocal _diffrn_measurement_device_type 'rigaku saturn' _diffrn_measurement_method '\w scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number 0 _diffrn_standards_interval_count 0 _diffrn_standards_interval_time 0 _diffrn_standards_decay_% 0 _diffrn_reflns_number 13512 _diffrn_reflns_av_R_equivalents 0.0544 _diffrn_reflns_av_sigmaI/netI 0.0453 _diffrn_reflns_limit_h_min -10 _diffrn_reflns_limit_h_max 10 _diffrn_reflns_limit_k_min -7 _diffrn_reflns_limit_k_max 10 _diffrn_reflns_limit_l_min -31 _diffrn_reflns_limit_l_max 30 _diffrn_reflns_theta_min 1.68 _diffrn_reflns_theta_max 27.93 _reflns_number_total 3568 _reflns_number_gt 2920 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'crystalclear' _computing_cell_refinement 'crystalclear' _computing_data_reduction 'crystalclear' _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^)+(0.0706P)^2^+0.2729P] 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 0.020(3) _refine_ls_extinction_expression 'Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^' _refine_ls_number_reflns 3568 _refine_ls_number_parameters 215 _refine_ls_number_restraints 1 _refine_ls_R_factor_all 0.0644 _refine_ls_R_factor_gt 0.0516 _refine_ls_wR_factor_ref 0.1361 _refine_ls_wR_factor_gt 0.1266 _refine_ls_goodness_of_fit_ref 1.051 _refine_ls_restrained_S_all 1.051 _refine_ls_shift/su_max 0.003 _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 O1 O 0.92195(16) -0.15678(16) 0.79058(5) 0.0311(3) Uani 1 1 d . . . O2 O -0.09522(14) 0.20532(16) 0.56822(5) 0.0287(3) Uani 1 1 d . . . O3 O 0.21098(15) 0.29799(16) 0.45316(5) 0.0301(3) Uani 1 1 d . . . O4 O 0.48371(14) 0.38046(15) 0.43930(5) 0.0239(3) Uani 1 1 d . . . N1 N 0.61891(16) 0.08181(16) 0.62438(5) 0.0190(3) Uani 1 1 d D . . H1 H 0.7038(18) 0.133(2) 0.6071(7) 0.023 Uiso 1 1 d D . . N2 N 0.17781(15) 0.11540(17) 0.55546(5) 0.0199(3) Uani 1 1 d . . . C1 C 0.44916(19) 0.05546(19) 0.60349(6) 0.0184(3) Uani 1 1 d . . . C2 C 0.36298(18) 0.14018(19) 0.55653(6) 0.0178(3) Uani 1 1 d . . . C3 C 0.1270(2) -0.0606(2) 0.56419(7) 0.0233(4) Uani 1 1 d . . . H3A H 0.1815 -0.1333 0.5371 0.028 Uiso 1 1 calc R . . H3B H -0.0010 -0.0719 0.5585 0.028 Uiso 1 1 calc R . . C4 C 0.1855(2) -0.1159(2) 0.62276(7) 0.0239(4) Uani 1 1 d . . . H4A H 0.1070 -0.0677 0.6494 0.029 Uiso 1 1 calc R . . H4B H 0.1797 -0.2394 0.6255 0.029 Uiso 1 1 calc R . . C5 C 0.36805(19) -0.05827(19) 0.63635(6) 0.0188(3) Uani 1 1 d . . . C6 C 0.49210(19) -0.10289(19) 0.67981(6) 0.0194(3) Uani 1 1 d . . . C7 C 0.4889(2) -0.2089(2) 0.72596(7) 0.0235(4) Uani 1 1 d . . . H7 H 0.3870 -0.2711 0.7326 0.028 Uiso 1 1 calc R . . C8 C 0.6347(2) -0.2215(2) 0.76132(7) 0.0263(4) Uani 1 1 d . . . H8 H 0.6336 -0.2932 0.7925 0.032 Uiso 1 1 calc R . . C9 C 0.7863(2) -0.1290(2) 0.75176(7) 0.0235(4) Uani 1 1 d . . . C10 C 0.7952(2) -0.0231(2) 0.70720(7) 0.0216(3) Uani 1 1 d . . . H10 H 0.8970 0.0400 0.7012 0.026 Uiso 1 1 calc R . . C11 C 0.64664(19) -0.01351(19) 0.67126(6) 0.0187(3) Uani 1 1 d . . . C12 C 1.0739(2) -0.0580(3) 0.78682(8) 0.0376(5) Uani 1 1 d . . . H12A H 1.1227 -0.0770 0.7510 0.056 Uiso 1 1 calc R . . H12B H 1.1600 -0.0893 0.8165 0.056 Uiso 1 1 calc R . . H12C H 1.0440 0.0605 0.7904 0.056 Uiso 1 1 calc R . . C13 C 0.44637(19) 0.22558(19) 0.51823(6) 0.0194(3) Uani 1 1 d . . . H13 H 0.5690 0.2374 0.5240 0.023 Uiso 1 1 calc R . . C14 C 0.36356(19) 0.30175(19) 0.46836(7) 0.0203(3) Uani 1 1 d . . . C15 C 0.4114(2) 0.4605(2) 0.38968(7) 0.0280(4) Uani 1 1 d . . . H15A H 0.3517 0.3769 0.3658 0.042 Uiso 1 1 calc R . . H15B H 0.5054 0.5122 0.3701 0.042 Uiso 1 1 calc R . . H15C H 0.3282 0.5468 0.3995 0.042 Uiso 1 1 calc R . . C16 C 0.06035(19) 0.2398(2) 0.56417(6) 0.0214(3) Uani 1 1 d . . . C17 C 0.1214(2) 0.4168(2) 0.57127(7) 0.0263(4) Uani 1 1 d . . . H17A H 0.0254 0.4933 0.5608 0.040 Uiso 1 1 calc R . . H17B H 0.2182 0.4370 0.5477 0.040 Uiso 1 1 calc R . . H17C H 0.1605 0.4359 0.6099 0.040 Uiso 1 1 calc R . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 O1 0.0297(6) 0.0362(7) 0.0262(7) 0.0081(5) -0.0072(5) 0.0001(5) O2 0.0147(5) 0.0393(7) 0.0323(7) 0.0036(5) 0.0042(5) -0.0040(5) O3 0.0206(6) 0.0363(7) 0.0326(7) 0.0080(5) -0.0054(5) -0.0046(5) O4 0.0228(6) 0.0279(6) 0.0212(6) 0.0071(5) 0.0017(4) -0.0023(5) N1 0.0149(6) 0.0219(7) 0.0204(7) 0.0037(5) 0.0022(5) -0.0011(5) N2 0.0145(6) 0.0222(7) 0.0228(7) 0.0015(5) 0.0007(5) -0.0044(5) C1 0.0160(7) 0.0192(8) 0.0203(8) -0.0015(6) 0.0024(6) -0.0010(5) C2 0.0140(7) 0.0187(7) 0.0205(8) -0.0018(6) 0.0009(6) -0.0005(5) C3 0.0227(7) 0.0223(8) 0.0249(9) -0.0003(6) -0.0001(6) -0.0076(6) C4 0.0225(8) 0.0220(8) 0.0271(9) 0.0013(7) 0.0016(7) -0.0065(6) C5 0.0194(7) 0.0174(7) 0.0198(8) -0.0018(6) 0.0040(6) -0.0018(6) C6 0.0216(7) 0.0169(7) 0.0200(8) -0.0007(6) 0.0044(6) 0.0004(6) C7 0.0250(8) 0.0211(8) 0.0248(8) 0.0027(6) 0.0038(7) -0.0012(6) C8 0.0313(9) 0.0244(9) 0.0235(8) 0.0068(7) 0.0036(7) 0.0002(7) C9 0.0229(8) 0.0253(8) 0.0221(8) 0.0004(6) -0.0014(6) 0.0043(6) C10 0.0195(7) 0.0219(8) 0.0236(8) 0.0015(6) 0.0029(6) 0.0022(6) C11 0.0202(7) 0.0169(7) 0.0193(7) 0.0002(6) 0.0045(6) 0.0024(6) C12 0.0290(9) 0.0494(13) 0.0331(10) 0.0062(9) -0.0090(8) -0.0043(8) C13 0.0174(7) 0.0202(8) 0.0206(8) 0.0001(6) 0.0015(6) -0.0008(6) C14 0.0198(7) 0.0186(8) 0.0225(8) -0.0005(6) 0.0011(6) -0.0019(6) C15 0.0336(9) 0.0284(9) 0.0214(8) 0.0062(7) -0.0018(7) -0.0008(7) C16 0.0164(7) 0.0300(9) 0.0178(7) 0.0016(6) 0.0008(6) -0.0024(6) C17 0.0217(8) 0.0267(9) 0.0307(9) -0.0010(7) 0.0011(7) 0.0012(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 O1 C9 1.380(2) . ? O1 C12 1.418(2) . ? O2 C16 1.2378(18) . ? O3 C14 1.2090(19) . ? O4 C14 1.3517(18) . ? O4 C15 1.445(2) . ? N1 C11 1.375(2) . ? N1 C1 1.3875(19) . ? N1 H1 0.897(9) . ? N2 C16 1.368(2) . ? N2 C2 1.4367(18) . ? N2 C3 1.478(2) . ? C1 C5 1.383(2) . ? C1 C2 1.451(2) . ? C2 C13 1.347(2) . ? C3 C4 1.530(2) . ? C3 H3A 0.9900 . ? C3 H3B 0.9900 . ? C4 C5 1.495(2) . ? C4 H4A 0.9900 . ? C4 H4B 0.9900 . ? C5 C6 1.424(2) . ? C6 C7 1.406(2) . ? C6 C11 1.413(2) . ? C7 C8 1.374(2) . ? C7 H7 0.9500 . ? C8 C9 1.412(2) . ? C8 H8 0.9500 . ? C9 C10 1.379(2) . ? C10 C11 1.397(2) . ? C10 H10 0.9500 . ? C12 H12A 0.9800 . ? C12 H12B 0.9800 . ? C12 H12C 0.9800 . ? C13 C14 1.465(2) . ? C13 H13 0.9500 . ? C15 H15A 0.9800 . ? C15 H15B 0.9800 . ? C15 H15C 0.9800 . ? C16 C17 1.497(2) . ? C17 H17A 0.9800 . ? C17 H17B 0.9800 . ? C17 H17C 0.9800 . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C9 O1 C12 117.27(13) . . ? C14 O4 C15 113.62(12) . . ? C11 N1 C1 108.26(12) . . ? C11 N1 H1 124.0(12) . . ? C1 N1 H1 126.5(12) . . ? C16 N2 C2 124.08(13) . . ? C16 N2 C3 119.08(13) . . ? C2 N2 C3 113.52(12) . . ? C5 C1 N1 109.67(14) . . ? C5 C1 C2 124.01(14) . . ? N1 C1 C2 126.22(13) . . ? C13 C2 N2 124.80(14) . . ? C13 C2 C1 124.39(13) . . ? N2 C2 C1 110.78(13) . . ? N2 C3 C4 110.04(13) . . ? N2 C3 H3A 109.7 . . ? C4 C3 H3A 109.7 . . ? N2 C3 H3B 109.7 . . ? C4 C3 H3B 109.7 . . ? H3A C3 H3B 108.2 . . ? C5 C4 C3 109.55(13) . . ? C5 C4 H4A 109.8 . . ? C3 C4 H4A 109.8 . . ? C5 C4 H4B 109.8 . . ? C3 C4 H4B 109.8 . . ? H4A C4 H4B 108.2 . . ? C1 C5 C6 106.64(13) . . ? C1 C5 C4 121.74(15) . . ? C6 C5 C4 131.59(14) . . ? C7 C6 C11 118.52(15) . . ? C7 C6 C5 134.24(15) . . ? C11 C6 C5 107.23(13) . . ? C8 C7 C6 119.24(15) . . ? C8 C7 H7 120.4 . . ? C6 C7 H7 120.4 . . ? C7 C8 C9 120.67(15) . . ? C7 C8 H8 119.7 . . ? C9 C8 H8 119.7 . . ? C10 C9 O1 124.24(15) . . ? C10 C9 C8 122.11(15) . . ? O1 C9 C8 113.65(14) . . ? C9 C10 C11 116.47(15) . . ? C9 C10 H10 121.8 . . ? C11 C10 H10 121.8 . . ? N1 C11 C10 128.81(14) . . ? N1 C11 C6 108.19(13) . . ? C10 C11 C6 122.97(14) . . ? O1 C12 H12A 109.5 . . ? O1 C12 H12B 109.5 . . ? H12A C12 H12B 109.5 . . ? O1 C12 H12C 109.5 . . ? H12A C12 H12C 109.5 . . ? H12B C12 H12C 109.5 . . ? C2 C13 C14 125.41(14) . . ? C2 C13 H13 117.3 . . ? C14 C13 H13 117.3 . . ? O3 C14 O4 122.29(15) . . ? O3 C14 C13 127.35(15) . . ? O4 C14 C13 110.36(13) . . ? O4 C15 H15A 109.5 . . ? O4 C15 H15B 109.5 . . ? H15A C15 H15B 109.5 . . ? O4 C15 H15C 109.5 . . ? H15A C15 H15C 109.5 . . ? H15B C15 H15C 109.5 . . ? O2 C16 N2 120.09(15) . . ? O2 C16 C17 119.94(15) . . ? N2 C16 C17 119.91(13) . . ? C16 C17 H17A 109.5 . . ? C16 C17 H17B 109.5 . . ? H17A C17 H17B 109.5 . . ? C16 C17 H17C 109.5 . . ? H17A C17 H17C 109.5 . . ? H17B C17 H17C 109.5 . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag C11 N1 C1 C5 -0.79(17) . . . . ? C11 N1 C1 C2 175.60(14) . . . . ? C16 N2 C2 C13 -69.8(2) . . . . ? C3 N2 C2 C13 131.03(16) . . . . ? C16 N2 C2 C1 112.24(16) . . . . ? C3 N2 C2 C1 -46.89(17) . . . . ? C5 C1 C2 C13 -166.74(15) . . . . ? N1 C1 C2 C13 17.4(2) . . . . ? C5 C1 C2 N2 11.2(2) . . . . ? N1 C1 C2 N2 -164.72(14) . . . . ? C16 N2 C3 C4 -94.14(17) . . . . ? C2 N2 C3 C4 66.13(16) . . . . ? N2 C3 C4 C5 -44.70(17) . . . . ? N1 C1 C5 C6 0.67(17) . . . . ? C2 C1 C5 C6 -175.81(14) . . . . ? N1 C1 C5 C4 -177.73(13) . . . . ? C2 C1 C5 C4 5.8(2) . . . . ? C3 C4 C5 C1 11.8(2) . . . . ? C3 C4 C5 C6 -166.18(15) . . . . ? C1 C5 C6 C7 178.95(16) . . . . ? C4 C5 C6 C7 -2.9(3) . . . . ? C1 C5 C6 C11 -0.31(17) . . . . ? C4 C5 C6 C11 177.88(16) . . . . ? C11 C6 C7 C8 0.4(2) . . . . ? C5 C6 C7 C8 -178.79(16) . . . . ? C6 C7 C8 C9 0.2(2) . . . . ? C12 O1 C9 C10 6.0(2) . . . . ? C12 O1 C9 C8 -174.63(16) . . . . ? C7 C8 C9 C10 0.0(3) . . . . ? C7 C8 C9 O1 -179.33(15) . . . . ? O1 C9 C10 C11 178.42(15) . . . . ? C8 C9 C10 C11 -0.9(2) . . . . ? C1 N1 C11 C10 -177.51(15) . . . . ? C1 N1 C11 C6 0.58(17) . . . . ? C9 C10 C11 N1 179.39(15) . . . . ? C9 C10 C11 C6 1.6(2) . . . . ? C7 C6 C11 N1 -179.56(13) . . . . ? C5 C6 C11 N1 -0.16(17) . . . . ? C7 C6 C11 C10 -1.3(2) . . . . ? C5 C6 C11 C10 178.06(14) . . . . ? N2 C2 C13 C14 -2.4(3) . . . . ? C1 C2 C13 C14 175.28(14) . . . . ? C15 O4 C14 O3 1.0(2) . . . . ? C15 O4 C14 C13 -179.35(13) . . . . ? C2 C13 C14 O3 -1.5(3) . . . . ? C2 C13 C14 O4 178.92(15) . . . . ? C2 N2 C16 O2 -172.53(14) . . . . ? C3 N2 C16 O2 -14.5(2) . . . . ? C2 N2 C16 C17 4.8(2) . . . . ? C3 N2 C16 C17 162.83(14) . . . . ? loop_ _geom_hbond_atom_site_label_D _geom_hbond_atom_site_label_H _geom_hbond_atom_site_label_A _geom_hbond_distance_DH _geom_hbond_distance_HA _geom_hbond_distance_DA _geom_hbond_angle_DHA _geom_hbond_site_symmetry_A N1 H1 O2 0.897(9) 1.947(10) 2.8346(18) 170.1(17) 1_655 _diffrn_measured_fraction_theta_max 0.998 _diffrn_reflns_theta_full 27.93 _diffrn_measured_fraction_theta_full 0.998 _refine_diff_density_max 0.286 _refine_diff_density_min -0.262 _refine_diff_density_rms 0.056