# Supplementary Material (ESI) for Organic & Biomolecular Chemistry # This journal is (c) The Royal Society of Chemistry 2010 data_global _journal_name_full Org.Biomol.Chem. _journal_coden_Cambridge 0177 _journal_volume ? _journal_page_first ? _journal_year ? _publ_contact_author_name C.R.Ramanathan _publ_contact_author_email crrnath.che@pondiuni.edu.in _publ_section_title ; An unusual reactivity of BBr3: Accessing tetrahydroisoquinoline units from N-phenethylimides ; loop_ _publ_author_name C.R.Ramanathan J.Selvakumar A.Makriyannis #TrackingRef '- 3c-jsiii162-768894.cif' data_jsiii162 _database_code_depnum_ccdc_archive 'CCDC 768894' #TrackingRef '- 3c-jsiii162-768894.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; 12b-Hydroxy-3,4-dimethoxy-5,12b-dihydro-6H-isoindolo[1,2-a]isoquinolin-8-one ; _chemical_name_common ;12b-Hydroxy-3,4-dimethoxy-5,12b-dihydro-6H-isoindolo(1,2- a)isoquinolin-8-one ; _chemical_melting_point 471 _chemical_formula_moiety 'C18 H17 N O4' _chemical_formula_sum 'C18 H17 N O4' _chemical_formula_weight 311.33 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 Triclinic _symmetry_space_group_name_H-M 'P -1' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 8.0395(2) _cell_length_b 8.2771(3) _cell_length_c 11.8814(3) _cell_angle_alpha 102.552(2) _cell_angle_beta 95.117(2) _cell_angle_gamma 102.507(2) _cell_volume 745.68(4) _cell_formula_units_Z 2 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used 7830 _cell_measurement_theta_min 2.55 _cell_measurement_theta_max 30.42 _exptl_crystal_description block _exptl_crystal_colour colorless _exptl_crystal_size_max 0.24 _exptl_crystal_size_mid 0.20 _exptl_crystal_size_min 0.16 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.387 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 328 _exptl_absorpt_coefficient_mu 0.098 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.9767 _exptl_absorpt_correction_T_max 0.9844 _exptl_absorpt_process_details 'SADABS (Bruker 1999)' _exptl_special_details ; ? ; _diffrn_ambient_temperature 293(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Bruker AXS Kappa Apex2 CCD Diffractometer' _diffrn_measurement_method '\w and \f scan' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 18825 _diffrn_reflns_av_R_equivalents 0.0256 _diffrn_reflns_av_sigmaI/netI 0.0215 _diffrn_reflns_limit_h_min -11 _diffrn_reflns_limit_h_max 11 _diffrn_reflns_limit_k_min -11 _diffrn_reflns_limit_k_max 11 _diffrn_reflns_limit_l_min -16 _diffrn_reflns_limit_l_max 16 _diffrn_reflns_theta_min 2.60 _diffrn_reflns_theta_max 30.48 _reflns_number_total 4525 _reflns_number_gt 3493 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'APEX2 (Bruker, 2004)' _computing_cell_refinement 'APEX2/SAINT (Bruker, 2004)' _computing_data_reduction 'SAINT/XPREP (Bruker, 2004)' _computing_structure_solution 'SHELXL-97 (Sheldrick, 1997)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'ORTEP3 (Farrugia, 1997) and Mercury (Bruno et al., 2002)' _computing_publication_material 'SHELXL-97 (Sheldrick, 1997)' _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^)+(0.0661P)^2^+0.1102P] 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 4525 _refine_ls_number_parameters 208 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0590 _refine_ls_R_factor_gt 0.0440 _refine_ls_wR_factor_ref 0.1291 _refine_ls_wR_factor_gt 0.1180 _refine_ls_goodness_of_fit_ref 1.041 _refine_ls_restrained_S_all 1.041 _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 C6 C 0.17700(14) 0.77925(14) 0.81698(9) 0.0320(2) Uani 1 1 d . . . N1 N 0.03132(12) 0.90140(13) 0.64431(8) 0.0356(2) Uani 1 1 d . . . O2 O 0.23971(11) 0.79095(11) 0.54378(7) 0.0397(2) Uani 1 1 d . . . H2 H 0.2023 0.8148 0.4846 0.060 Uiso 1 1 calc R . . C4 C 0.42639(15) 0.75287(14) 0.93634(9) 0.0355(2) Uani 1 1 d . . . C1 C 0.28663(13) 0.85638(13) 0.74826(9) 0.0305(2) Uani 1 1 d . . . C16 C 0.21476(14) 0.90810(14) 0.64265(9) 0.0317(2) Uani 1 1 d . . . O3 O 0.13884(11) 0.64479(11) 0.97306(7) 0.0428(2) Uani 1 1 d . . . O4 O 0.48198(12) 0.69676(12) 1.02886(8) 0.0467(2) Uani 1 1 d . . . O1 O -0.15652(11) 1.07451(13) 0.64651(7) 0.0456(2) Uani 1 1 d . . . C15 C 0.28349(15) 1.09237(14) 0.63854(9) 0.0335(2) Uani 1 1 d . . . C2 C 0.46220(15) 0.87921(15) 0.77389(10) 0.0362(2) Uani 1 1 d . . . H2A H 0.5346 0.9295 0.7277 0.043 Uiso 1 1 calc R . . C3 C 0.53268(15) 0.82851(16) 0.86736(11) 0.0386(2) Uani 1 1 d . . . H3 H 0.6514 0.8454 0.8836 0.046 Uiso 1 1 calc R . . C10 C 0.14952(15) 1.17323(14) 0.63946(9) 0.0346(2) Uani 1 1 d . . . C5 C 0.24887(14) 0.72902(14) 0.91089(9) 0.0334(2) Uani 1 1 d . . . C9 C -0.01080(15) 1.05045(15) 0.64444(9) 0.0349(2) Uani 1 1 d . . . C7 C -0.01623(15) 0.74752(18) 0.79294(11) 0.0418(3) Uani 1 1 d . . . H7A H -0.0538 0.8328 0.8477 0.050 Uiso 1 1 calc R . . H7B H -0.0685 0.6365 0.8048 0.050 Uiso 1 1 calc R . . C8 C -0.07717(15) 0.75381(17) 0.66968(11) 0.0415(3) Uani 1 1 d . . . H8A H -0.0700 0.6508 0.6149 0.050 Uiso 1 1 calc R . . H8B H -0.1961 0.7619 0.6627 0.050 Uiso 1 1 calc R . . C11 C 0.17513(19) 1.34181(16) 0.63459(11) 0.0444(3) Uani 1 1 d . . . H11 H 0.0847 1.3955 0.6370 0.053 Uiso 1 1 calc R . . C12 C 0.3392(2) 1.42846(17) 0.62606(13) 0.0530(3) Uani 1 1 d . . . H12 H 0.3604 1.5423 0.6229 0.064 Uiso 1 1 calc R . . C14 C 0.44652(17) 1.17745(17) 0.62826(12) 0.0447(3) Uani 1 1 d . . . H14 H 0.5367 1.1234 0.6255 0.054 Uiso 1 1 calc R . . C13 C 0.4720(2) 1.34633(18) 0.62216(13) 0.0536(3) Uani 1 1 d . . . H13 H 0.5813 1.4059 0.6153 0.064 Uiso 1 1 calc R . . C18 C 0.66098(19) 0.70934(19) 1.05312(13) 0.0523(3) Uani 1 1 d . . . H18A H 0.6831 0.6656 1.1200 0.079 Uiso 1 1 calc R . . H18B H 0.7228 0.8267 1.0686 0.079 Uiso 1 1 calc R . . H18C H 0.6982 0.6442 0.9872 0.079 Uiso 1 1 calc R . . C17 C 0.1399(2) 0.7326(2) 1.08998(12) 0.0578(4) Uani 1 1 d . . . H17A H 0.0592 0.6633 1.1255 0.087 Uiso 1 1 calc R . . H17B H 0.1080 0.8381 1.0910 0.087 Uiso 1 1 calc R . . H17C H 0.2532 0.7558 1.1325 0.087 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 C6 0.0286(5) 0.0324(5) 0.0368(5) 0.0107(4) 0.0065(4) 0.0080(4) N1 0.0274(5) 0.0414(5) 0.0435(5) 0.0166(4) 0.0065(4) 0.0131(4) O2 0.0473(5) 0.0417(4) 0.0373(4) 0.0117(3) 0.0095(3) 0.0223(4) C4 0.0373(6) 0.0324(5) 0.0366(5) 0.0099(4) -0.0011(4) 0.0089(4) C1 0.0287(5) 0.0307(5) 0.0361(5) 0.0115(4) 0.0071(4) 0.0113(4) C16 0.0285(5) 0.0351(5) 0.0370(5) 0.0136(4) 0.0086(4) 0.0131(4) O3 0.0454(5) 0.0421(5) 0.0377(4) 0.0154(3) 0.0064(3) -0.0023(4) O4 0.0440(5) 0.0531(5) 0.0462(5) 0.0226(4) -0.0028(4) 0.0116(4) O1 0.0377(5) 0.0660(6) 0.0439(4) 0.0180(4) 0.0094(3) 0.0295(4) C15 0.0369(6) 0.0345(5) 0.0349(5) 0.0138(4) 0.0087(4) 0.0144(4) C2 0.0301(5) 0.0388(6) 0.0444(6) 0.0171(4) 0.0080(4) 0.0101(4) C3 0.0283(5) 0.0415(6) 0.0478(6) 0.0152(5) 0.0018(4) 0.0092(5) C10 0.0396(6) 0.0382(6) 0.0307(5) 0.0091(4) 0.0053(4) 0.0184(5) C5 0.0344(6) 0.0301(5) 0.0349(5) 0.0101(4) 0.0053(4) 0.0040(4) C9 0.0360(6) 0.0464(6) 0.0282(4) 0.0112(4) 0.0055(4) 0.0201(5) C7 0.0283(6) 0.0542(7) 0.0480(6) 0.0230(5) 0.0091(5) 0.0086(5) C8 0.0282(6) 0.0484(7) 0.0495(6) 0.0192(5) 0.0033(5) 0.0065(5) C11 0.0559(8) 0.0379(6) 0.0440(6) 0.0091(5) 0.0037(5) 0.0236(6) C12 0.0699(10) 0.0323(6) 0.0580(8) 0.0144(5) 0.0049(7) 0.0135(6) C14 0.0403(7) 0.0431(7) 0.0594(7) 0.0229(6) 0.0161(5) 0.0146(5) C13 0.0526(8) 0.0435(7) 0.0676(9) 0.0242(6) 0.0129(7) 0.0055(6) C18 0.0488(8) 0.0538(8) 0.0527(7) 0.0153(6) -0.0124(6) 0.0144(6) C17 0.0616(9) 0.0604(9) 0.0450(7) 0.0101(6) 0.0180(6) -0.0002(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 C6 C5 1.3937(15) . ? C6 C1 1.4008(14) . ? C6 C7 1.5084(16) . ? N1 C9 1.3479(15) . ? N1 C8 1.4455(15) . ? N1 C16 1.4659(14) . ? O2 C16 1.4112(13) . ? C4 O4 1.3594(13) . ? C4 C3 1.3820(16) . ? C4 C5 1.3937(17) . ? C1 C2 1.3797(15) . ? C1 C16 1.5175(14) . ? C16 C15 1.5186(15) . ? O3 C5 1.3739(13) . ? O3 C17 1.4193(16) . ? O4 C18 1.4188(17) . ? O1 C9 1.2316(14) . ? C15 C14 1.3765(17) . ? C15 C10 1.3853(15) . ? C2 C3 1.3870(16) . ? C10 C11 1.3804(17) . ? C10 C9 1.4731(17) . ? C7 C8 1.5178(17) . ? C11 C12 1.382(2) . ? C12 C13 1.383(2) . ? C14 C13 1.3870(19) . ? 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 C5 C6 C1 118.85(10) . . ? C5 C6 C7 118.62(9) . . ? C1 C6 C7 122.53(9) . . ? C9 N1 C8 125.77(10) . . ? C9 N1 C16 114.41(10) . . ? C8 N1 C16 118.45(9) . . ? O4 C4 C3 124.64(11) . . ? O4 C4 C5 116.13(10) . . ? C3 C4 C5 119.23(10) . . ? C2 C1 C6 119.61(10) . . ? C2 C1 C16 119.37(9) . . ? C6 C1 C16 120.96(9) . . ? O2 C16 N1 110.88(9) . . ? O2 C16 C1 106.55(8) . . ? N1 C16 C1 109.77(8) . . ? O2 C16 C15 112.59(8) . . ? N1 C16 C15 100.90(8) . . ? C1 C16 C15 116.12(9) . . ? C5 O3 C17 116.01(9) . . ? C4 O4 C18 117.74(10) . . ? C14 C15 C10 120.38(11) . . ? C14 C15 C16 130.10(10) . . ? C10 C15 C16 109.41(10) . . ? C1 C2 C3 121.18(10) . . ? C4 C3 C2 119.95(11) . . ? C11 C10 C15 121.76(11) . . ? C11 C10 C9 129.39(11) . . ? C15 C10 C9 108.84(10) . . ? O3 C5 C4 120.77(10) . . ? O3 C5 C6 117.91(10) . . ? C4 C5 C6 121.18(10) . . ? O1 C9 N1 125.51(12) . . ? O1 C9 C10 128.07(11) . . ? N1 C9 C10 106.41(9) . . ? C6 C7 C8 112.05(9) . . ? N1 C8 C7 108.34(10) . . ? C10 C11 C12 118.01(12) . . ? C11 C12 C13 120.18(12) . . ? C15 C14 C13 117.88(12) . . ? C12 C13 C14 121.76(13) . . ? _diffrn_measured_fraction_theta_max 0.994 _diffrn_reflns_theta_full 30.48 _diffrn_measured_fraction_theta_full 0.994 _refine_diff_density_max 0.246 _refine_diff_density_min -0.221 _refine_diff_density_rms 0.046 # Attachment '- 3d-epu148-768895.cif' data_epu148 _database_code_depnum_ccdc_archive 'CCDC 768895' #TrackingRef '- 3d-epu148-768895.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; 12b-Hydroxy-1,2,3-trimethoxy-5,12b-dihydro-6H-isoindolo[1,2-a]isoquinolin-8-one ; _chemical_name_common ;12b-Hydroxy-1,2,3-trimethoxy-5,12b-dihydro-6H-isoindolo(1,2- a)isoquinolin-8-one ; _chemical_melting_point 452 _chemical_formula_moiety 'C19 H19 N O5' _chemical_formula_sum 'C19 H19 N O5' _chemical_formula_weight 341.35 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 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 12.353(3) _cell_length_b 15.906(4) _cell_length_c 8.5238(19) _cell_angle_alpha 90.00 _cell_angle_beta 99.701(3) _cell_angle_gamma 90.00 _cell_volume 1650.9(6) _cell_formula_units_Z 4 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used 4526 _cell_measurement_theta_min 2.56 _cell_measurement_theta_max 25.98 _exptl_crystal_description plate _exptl_crystal_colour colorless _exptl_crystal_size_max 0.32 _exptl_crystal_size_mid 0.25 _exptl_crystal_size_min 0.10 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.373 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 720 _exptl_absorpt_coefficient_mu 0.100 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.9687 _exptl_absorpt_correction_T_max 0.9901 _exptl_absorpt_process_details Sadabs _exptl_special_details ; ? ; _diffrn_ambient_temperature 293(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type '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 11793 _diffrn_reflns_av_R_equivalents 0.0323 _diffrn_reflns_av_sigmaI/netI 0.0325 _diffrn_reflns_limit_h_min -15 _diffrn_reflns_limit_h_max 15 _diffrn_reflns_limit_k_min -15 _diffrn_reflns_limit_k_max 19 _diffrn_reflns_limit_l_min -9 _diffrn_reflns_limit_l_max 10 _diffrn_reflns_theta_min 1.67 _diffrn_reflns_theta_max 25.99 _reflns_number_total 3219 _reflns_number_gt 2546 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'Bruker SMART' _computing_data_reduction 'Bruker SAINT' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'ORTEP3 (Farrugia, 1997) and Mercury (Bruno et al., 2002)' _computing_publication_material 'SHELXL-97 (Sheldrick, 1997)' _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^)+(0.0502P)^2^+0.5156P] 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 3219 _refine_ls_number_parameters 226 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0766 _refine_ls_R_factor_gt 0.0589 _refine_ls_wR_factor_ref 0.1343 _refine_ls_wR_factor_gt 0.1265 _refine_ls_goodness_of_fit_ref 1.139 _refine_ls_restrained_S_all 1.139 _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 O3 O 0.22000(12) 0.88682(9) -0.00092(17) 0.0444(4) Uani 1 1 d . . . O1 O 0.39829(12) 1.08655(10) 0.62382(18) 0.0484(4) Uani 1 1 d . . . O2 O 0.38354(11) 0.86730(9) 0.29412(18) 0.0445(4) Uani 1 1 d . . . H2 H 0.4490 0.8792 0.3150 0.067 Uiso 1 1 calc R . . N1 N 0.34203(14) 0.96906(12) 0.4777(2) 0.0411(5) Uani 1 1 d . . . C1 C 0.20001(17) 0.91163(13) 0.2712(3) 0.0375(5) Uani 1 1 d . . . C16 C 0.32021(16) 0.93937(14) 0.3114(2) 0.0372(5) Uani 1 1 d . . . O4 O 0.00941(13) 0.83206(11) -0.0749(2) 0.0565(5) Uani 1 1 d . . . C15 C 0.35688(15) 1.01680(13) 0.2268(2) 0.0352(5) Uani 1 1 d . . . C10 C 0.39081(16) 1.07899(13) 0.3376(2) 0.0357(5) Uani 1 1 d . . . C9 C 0.37852(15) 1.04873(14) 0.4961(2) 0.0370(5) Uani 1 1 d . . . O5 O -0.11728(13) 0.81775(13) 0.1498(2) 0.0672(5) Uani 1 1 d . . . C3 C 0.04921(18) 0.85685(14) 0.0786(3) 0.0448(6) Uani 1 1 d . . . C2 C 0.15645(17) 0.88467(13) 0.1167(3) 0.0394(5) Uani 1 1 d . . . C6 C 0.13364(18) 0.90639(14) 0.3882(3) 0.0427(5) Uani 1 1 d . . . C4 C -0.01574(17) 0.85083(15) 0.1962(3) 0.0493(6) Uani 1 1 d . . . C8 C 0.29811(19) 0.92299(16) 0.5989(3) 0.0490(6) Uani 1 1 d . . . H8A H 0.3239 0.9473 0.7028 0.059 Uiso 1 1 calc R . . H8B H 0.3217 0.8648 0.6004 0.059 Uiso 1 1 calc R . . C5 C 0.02696(18) 0.87574(15) 0.3489(3) 0.0503(6) Uani 1 1 d . . . H5 H -0.0165 0.8720 0.4276 0.060 Uiso 1 1 calc R . . C13 C 0.4115(2) 1.10503(16) 0.0298(3) 0.0546(6) Uani 1 1 d . . . H13 H 0.4192 1.1141 -0.0755 0.066 Uiso 1 1 calc R . . C7 C 0.1747(2) 0.92825(18) 0.5594(3) 0.0540(6) Uani 1 1 d . . . H7A H 0.1426 0.8900 0.6274 0.065 Uiso 1 1 calc R . . H7B H 0.1514 0.9848 0.5803 0.065 Uiso 1 1 calc R . . C14 C 0.36891(19) 1.02943(15) 0.0709(3) 0.0463(6) Uani 1 1 d . . . H14 H 0.3488 0.9879 -0.0052 0.056 Uiso 1 1 calc R . . C11 C 0.43261(19) 1.15443(15) 0.2965(3) 0.0478(6) Uani 1 1 d . . . H11 H 0.4535 1.1958 0.3726 0.057 Uiso 1 1 calc R . . C12 C 0.4428(2) 1.16729(16) 0.1403(3) 0.0547(7) Uani 1 1 d . . . H12 H 0.4708 1.2178 0.1094 0.066 Uiso 1 1 calc R . . C17 C 0.2534(2) 0.80537(16) -0.0462(3) 0.0570(7) Uani 1 1 d . . . H17A H 0.2973 0.8112 -0.1284 0.085 Uiso 1 1 calc R . . H17B H 0.1895 0.7722 -0.0851 0.085 Uiso 1 1 calc R . . H17C H 0.2956 0.7781 0.0445 0.085 Uiso 1 1 calc R . . C18 C -0.0581(3) 0.89355(19) -0.1648(3) 0.0736(8) Uani 1 1 d . . . H18A H -0.0830 0.8727 -0.2703 0.110 Uiso 1 1 calc R . . H18B H -0.0166 0.9441 -0.1703 0.110 Uiso 1 1 calc R . . H18C H -0.1203 0.9053 -0.1143 0.110 Uiso 1 1 calc R . . C19 C -0.1873(2) 0.8116(2) 0.2649(4) 0.0774(9) Uani 1 1 d . . . H19A H -0.2559 0.7869 0.2172 0.116 Uiso 1 1 calc R . . H19B H -0.2002 0.8667 0.3039 0.116 Uiso 1 1 calc R . . H19C H -0.1532 0.7770 0.3516 0.116 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 O3 0.0517(9) 0.0408(9) 0.0402(9) -0.0047(7) 0.0064(7) -0.0058(7) O1 0.0463(9) 0.0595(11) 0.0393(9) -0.0152(8) 0.0067(7) -0.0062(8) O2 0.0391(8) 0.0398(9) 0.0519(10) -0.0019(7) -0.0003(7) -0.0003(7) N1 0.0462(10) 0.0471(12) 0.0286(9) -0.0009(8) 0.0022(8) -0.0077(9) C1 0.0400(11) 0.0318(12) 0.0393(12) 0.0016(9) 0.0023(9) -0.0010(9) C16 0.0400(11) 0.0373(12) 0.0336(11) -0.0034(9) 0.0039(9) -0.0016(9) O4 0.0512(9) 0.0534(11) 0.0584(11) -0.0122(8) -0.0100(8) 0.0007(8) C15 0.0313(10) 0.0382(12) 0.0347(11) -0.0006(9) 0.0016(8) -0.0001(9) C10 0.0320(10) 0.0361(12) 0.0382(12) -0.0026(9) 0.0037(9) 0.0021(9) C9 0.0299(10) 0.0453(13) 0.0346(12) -0.0062(10) 0.0023(9) 0.0007(9) O5 0.0364(9) 0.0795(14) 0.0834(14) -0.0028(10) 0.0036(9) -0.0121(9) C3 0.0415(12) 0.0370(13) 0.0524(14) -0.0044(11) -0.0022(11) -0.0002(10) C2 0.0431(12) 0.0327(12) 0.0414(12) 0.0006(10) 0.0047(10) 0.0018(9) C6 0.0428(12) 0.0407(13) 0.0445(13) 0.0014(10) 0.0073(10) -0.0004(10) C4 0.0330(11) 0.0458(14) 0.0668(17) 0.0014(12) 0.0015(11) -0.0010(10) C8 0.0575(14) 0.0567(16) 0.0325(12) 0.0043(11) 0.0066(10) -0.0107(12) C5 0.0422(12) 0.0535(16) 0.0571(16) 0.0045(12) 0.0144(11) 0.0006(11) C13 0.0674(16) 0.0583(17) 0.0388(13) 0.0069(12) 0.0110(12) -0.0080(13) C7 0.0567(15) 0.0641(17) 0.0435(14) -0.0010(12) 0.0149(11) -0.0072(12) C14 0.0556(13) 0.0475(15) 0.0352(13) -0.0049(10) 0.0064(10) -0.0094(11) C11 0.0558(14) 0.0350(13) 0.0510(15) -0.0070(11) 0.0042(11) -0.0034(11) C12 0.0686(16) 0.0427(15) 0.0523(16) 0.0080(12) 0.0089(13) -0.0105(12) C17 0.0669(16) 0.0484(16) 0.0567(16) -0.0092(12) 0.0136(13) 0.0012(13) C18 0.0757(19) 0.078(2) 0.0598(18) 0.0074(15) -0.0103(15) 0.0029(16) C19 0.0383(14) 0.084(2) 0.111(3) 0.0020(19) 0.0148(15) -0.0075(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 O3 C2 1.374(3) . ? O3 C17 1.432(3) . ? O1 C9 1.232(2) . ? O2 C16 1.409(3) . ? N1 C9 1.345(3) . ? N1 C8 1.445(3) . ? N1 C16 1.475(3) . ? C1 C6 1.396(3) . ? C1 C2 1.403(3) . ? C1 C16 1.531(3) . ? C16 C15 1.534(3) . ? O4 C3 1.376(3) . ? O4 C18 1.423(3) . ? C15 C14 1.376(3) . ? C15 C10 1.383(3) . ? C10 C11 1.375(3) . ? C10 C9 1.466(3) . ? O5 C4 1.356(3) . ? O5 C19 1.416(3) . ? C3 C2 1.382(3) . ? C3 C4 1.388(3) . ? C6 C5 1.392(3) . ? C6 C7 1.503(3) . ? C4 C5 1.377(3) . ? C8 C7 1.508(3) . ? C13 C12 1.377(3) . ? C13 C14 1.381(3) . ? C11 C12 1.373(3) . ? 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 O3 C17 113.57(17) . . ? C9 N1 C8 123.60(18) . . ? C9 N1 C16 114.63(17) . . ? C8 N1 C16 119.66(18) . . ? C6 C1 C2 118.3(2) . . ? C6 C1 C16 121.45(19) . . ? C2 C1 C16 120.12(19) . . ? O2 C16 N1 110.24(16) . . ? O2 C16 C1 106.06(16) . . ? N1 C16 C1 108.68(17) . . ? O2 C16 C15 113.01(16) . . ? N1 C16 C15 100.03(16) . . ? C1 C16 C15 118.57(17) . . ? C3 O4 C18 113.48(19) . . ? C14 C15 C10 119.0(2) . . ? C14 C15 C16 131.27(19) . . ? C10 C15 C16 109.42(18) . . ? C11 C10 C15 122.2(2) . . ? C11 C10 C9 128.6(2) . . ? C15 C10 C9 109.15(19) . . ? O1 C9 N1 125.1(2) . . ? O1 C9 C10 128.2(2) . . ? N1 C9 C10 106.66(18) . . ? C4 O5 C19 117.9(2) . . ? O4 C3 C2 119.3(2) . . ? O4 C3 C4 120.6(2) . . ? C2 C3 C4 120.0(2) . . ? O3 C2 C3 118.6(2) . . ? O3 C2 C1 120.09(19) . . ? C3 C2 C1 121.3(2) . . ? C5 C6 C1 119.7(2) . . ? C5 C6 C7 117.7(2) . . ? C1 C6 C7 122.5(2) . . ? O5 C4 C5 125.1(2) . . ? O5 C4 C3 115.8(2) . . ? C5 C4 C3 119.1(2) . . ? N1 C8 C7 107.44(19) . . ? C4 C5 C6 121.6(2) . . ? C12 C13 C14 121.9(2) . . ? C6 C7 C8 111.53(19) . . ? C15 C14 C13 118.7(2) . . ? C12 C11 C10 118.5(2) . . ? C11 C12 C13 119.7(2) . . ? _diffrn_measured_fraction_theta_max 0.994 _diffrn_reflns_theta_full 25.00 _diffrn_measured_fraction_theta_full 1.000 _refine_diff_density_max 0.226 _refine_diff_density_min -0.180 _refine_diff_density_rms 0.038 # Attachment '- 3b-epu104_m-768896.cif' data_epu104_m _database_code_depnum_ccdc_archive 'CCDC 768896' #TrackingRef '- 3b-epu104_m-768896.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; 12b-Hydroxy-2,3-dimethoxy-5,12b-dihydro-6H-isoindolo[1,2-a]isoquinolin-8-one ; _chemical_name_common ;12b-Hydroxy-2,3-dimethoxy-5,12b-dihydro-6H-isoindolo(1,2- a)isoquinolin-8-one ; _chemical_melting_point 432 _chemical_formula_moiety 'C18 H17 N O4' _chemical_formula_sum 'C18 H17 N O4' _chemical_formula_weight 311.33 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 8.508(3) _cell_length_b 10.588(3) _cell_length_c 16.707(5) _cell_angle_alpha 90.00 _cell_angle_beta 93.589(5) _cell_angle_gamma 90.00 _cell_volume 1502.0(8) _cell_formula_units_Z 4 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used 2820 _cell_measurement_theta_min 2.28 _cell_measurement_theta_max 23.36 _exptl_crystal_description 'tiny plate' _exptl_crystal_colour colorless _exptl_crystal_size_max 0.30 _exptl_crystal_size_mid 0.12 _exptl_crystal_size_min 0.06 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.377 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 656 _exptl_absorpt_coefficient_mu 0.098 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.9713 _exptl_absorpt_correction_T_max 0.9942 _exptl_absorpt_process_details Sadabs _exptl_special_details ; ? ; _diffrn_ambient_temperature 293(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type '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 11199 _diffrn_reflns_av_R_equivalents 0.0510 _diffrn_reflns_av_sigmaI/netI 0.0580 _diffrn_reflns_limit_h_min -10 _diffrn_reflns_limit_h_max 9 _diffrn_reflns_limit_k_min -12 _diffrn_reflns_limit_k_max 13 _diffrn_reflns_limit_l_min -20 _diffrn_reflns_limit_l_max 20 _diffrn_reflns_theta_min 2.28 _diffrn_reflns_theta_max 25.85 _reflns_number_total 2894 _reflns_number_gt 1906 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'Bruker SMART' _computing_data_reduction 'Bruker SAINT' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'ORTEP3 (Farrugia, 1997) and Mercury (Bruno et al., 2002)' _computing_publication_material 'SHELXL-97 (Sheldrick, 1997)' _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^)+(0.0490P)^2^+0.4331P] 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 2894 _refine_ls_number_parameters 208 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0954 _refine_ls_R_factor_gt 0.0553 _refine_ls_wR_factor_ref 0.1305 _refine_ls_wR_factor_gt 0.1152 _refine_ls_goodness_of_fit_ref 1.021 _refine_ls_restrained_S_all 1.021 _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 O1 O 0.0429(2) 0.03334(15) 0.16035(10) 0.0499(5) Uani 1 1 d . . . N1 N -0.0465(2) 0.21886(17) 0.21324(11) 0.0382(5) Uani 1 1 d . . . O4 O -0.1147(2) 0.74465(15) 0.03209(10) 0.0511(5) Uani 1 1 d . . . O2 O -0.2325(2) 0.33013(15) 0.28764(10) 0.0494(5) Uani 1 1 d . . . H2 H -0.1680 0.3806 0.3074 0.074 Uiso 1 1 calc R . . C6 C -0.0127(3) 0.4511(2) 0.14347(13) 0.0345(5) Uani 1 1 d . . . O3 O -0.3935(2) 0.67163(17) 0.06135(13) 0.0657(6) Uani 1 1 d . . . C8 C 0.1027(3) 0.2798(2) 0.23324(15) 0.0431(6) Uani 1 1 d . . . H8A H 0.1864 0.2174 0.2364 0.052 Uiso 1 1 calc R . . H8B H 0.1003 0.3209 0.2850 0.052 Uiso 1 1 calc R . . C2 C -0.2916(3) 0.4871(2) 0.13386(15) 0.0423(6) Uani 1 1 d . . . H2A H -0.3921 0.4617 0.1458 0.051 Uiso 1 1 calc R . . C3 C -0.2738(3) 0.5956(2) 0.09089(15) 0.0416(6) Uani 1 1 d . . . C5 C 0.0046(3) 0.5625(2) 0.10011(13) 0.0390(6) Uani 1 1 d . . . H5 H 0.1052 0.5887 0.0889 0.047 Uiso 1 1 calc R . . C1 C -0.1625(3) 0.4136(2) 0.16009(13) 0.0339(5) Uani 1 1 d . . . C4 C -0.1221(3) 0.6344(2) 0.07360(13) 0.0378(6) Uani 1 1 d . . . C16 C -0.1901(3) 0.2959(2) 0.21030(14) 0.0380(6) Uani 1 1 d . . . C15 C -0.3097(3) 0.2029(2) 0.17469(14) 0.0390(6) Uani 1 1 d . . . C7 C 0.1337(3) 0.3769(2) 0.16898(15) 0.0435(6) Uani 1 1 d . . . H7A H 0.2151 0.4347 0.1894 0.052 Uiso 1 1 calc R . . H7B H 0.1720 0.3342 0.1227 0.052 Uiso 1 1 calc R . . C10 C -0.2335(3) 0.0944(2) 0.15163(13) 0.0383(6) Uani 1 1 d . . . C9 C -0.0640(3) 0.1071(2) 0.17415(13) 0.0371(6) Uani 1 1 d . . . C18 C 0.0374(3) 0.7926(2) 0.01790(16) 0.0520(7) Uani 1 1 d . . . H18A H 0.0267 0.8704 -0.0115 0.078 Uiso 1 1 calc R . . H18B H 0.0929 0.7323 -0.0126 0.078 Uiso 1 1 calc R . . H18C H 0.0951 0.8076 0.0682 0.078 Uiso 1 1 calc R . . C11 C -0.3153(3) -0.0057(2) 0.11646(15) 0.0496(7) Uani 1 1 d . . . H11 H -0.2631 -0.0777 0.1003 0.059 Uiso 1 1 calc R . . C12 C -0.4769(3) 0.0042(3) 0.10598(18) 0.0611(8) Uani 1 1 d . . . H12 H -0.5346 -0.0616 0.0818 0.073 Uiso 1 1 calc R . . C14 C -0.4716(3) 0.2108(2) 0.16574(17) 0.0547(7) Uani 1 1 d . . . H14 H -0.5240 0.2820 0.1828 0.066 Uiso 1 1 calc R . . C13 C -0.5542(3) 0.1104(3) 0.1308(2) 0.0659(8) Uani 1 1 d . . . H13 H -0.6634 0.1145 0.1239 0.079 Uiso 1 1 calc R . . C17 C -0.5487(3) 0.6398(3) 0.0793(2) 0.0776(10) Uani 1 1 d . . . H17A H -0.6210 0.7004 0.0551 0.116 Uiso 1 1 calc R . . H17B H -0.5565 0.6400 0.1363 0.116 Uiso 1 1 calc R . . H17C H -0.5742 0.5572 0.0585 0.116 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 0.0485(11) 0.0398(10) 0.0614(11) 0.0052(8) 0.0039(9) 0.0126(9) N1 0.0347(12) 0.0326(11) 0.0466(12) 0.0007(9) -0.0018(9) 0.0003(9) O4 0.0513(12) 0.0426(10) 0.0596(11) 0.0140(9) 0.0066(9) 0.0049(8) O2 0.0598(11) 0.0453(10) 0.0441(10) -0.0063(8) 0.0119(8) -0.0098(8) C6 0.0328(13) 0.0344(13) 0.0360(13) -0.0030(10) 0.0000(10) 0.0003(10) O3 0.0395(11) 0.0543(12) 0.1026(16) 0.0186(11) -0.0021(10) 0.0111(9) C8 0.0399(15) 0.0417(14) 0.0466(15) 0.0028(12) -0.0045(11) 0.0030(11) C2 0.0350(14) 0.0377(14) 0.0544(15) -0.0026(12) 0.0047(11) -0.0008(11) C3 0.0377(14) 0.0334(14) 0.0534(15) -0.0012(11) -0.0007(11) 0.0059(11) C5 0.0354(14) 0.0411(14) 0.0411(14) 0.0004(11) 0.0056(11) -0.0036(11) C1 0.0343(13) 0.0304(13) 0.0369(13) -0.0053(10) 0.0019(10) 0.0004(10) C4 0.0464(15) 0.0311(13) 0.0361(13) 0.0016(10) 0.0030(11) 0.0045(11) C16 0.0386(14) 0.0346(13) 0.0416(14) -0.0029(11) 0.0073(11) 0.0009(11) C15 0.0391(15) 0.0333(13) 0.0449(14) 0.0007(11) 0.0043(11) -0.0029(11) C7 0.0367(14) 0.0420(14) 0.0514(15) 0.0018(12) 0.0009(11) -0.0004(11) C10 0.0425(15) 0.0312(13) 0.0416(14) 0.0030(11) 0.0049(11) -0.0001(11) C9 0.0432(15) 0.0319(13) 0.0364(13) 0.0097(11) 0.0031(11) 0.0038(11) C18 0.0633(19) 0.0446(15) 0.0489(16) 0.0069(12) 0.0100(13) -0.0047(13) C11 0.0551(18) 0.0338(14) 0.0597(17) -0.0044(12) 0.0030(13) 0.0001(12) C12 0.0540(19) 0.0458(17) 0.082(2) -0.0086(15) -0.0069(15) -0.0118(14) C14 0.0397(16) 0.0403(15) 0.085(2) -0.0077(14) 0.0091(14) -0.0019(12) C13 0.0392(16) 0.0518(18) 0.106(2) -0.0069(17) 0.0014(15) -0.0064(14) C17 0.0392(18) 0.068(2) 0.125(3) 0.0050(19) -0.0018(17) 0.0122(15) _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 1.231(3) . ? N1 C9 1.355(3) . ? N1 C8 1.444(3) . ? N1 C16 1.468(3) . ? O4 C4 1.361(3) . ? O4 C18 1.424(3) . ? O2 C16 1.410(3) . ? C6 C1 1.380(3) . ? C6 C5 1.397(3) . ? C6 C7 1.511(3) . ? O3 C3 1.366(3) . ? O3 C17 1.413(3) . ? C8 C7 1.522(3) . ? C2 C3 1.368(3) . ? C2 C1 1.394(3) . ? C3 C4 1.401(3) . ? C5 C4 1.370(3) . ? C1 C16 1.529(3) . ? C16 C15 1.511(3) . ? C15 C14 1.378(3) . ? C15 C10 1.386(3) . ? C10 C11 1.379(3) . ? C10 C9 1.473(3) . ? C11 C12 1.380(4) . ? C12 C13 1.379(4) . ? C14 C13 1.384(4) . ? 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 N1 C8 124.77(19) . . ? C9 N1 C16 113.73(18) . . ? C8 N1 C16 118.54(18) . . ? C4 O4 C18 117.57(19) . . ? C1 C6 C5 118.4(2) . . ? C1 C6 C7 123.3(2) . . ? C5 C6 C7 118.3(2) . . ? C3 O3 C17 117.9(2) . . ? N1 C8 C7 109.12(19) . . ? C3 C2 C1 121.5(2) . . ? O3 C3 C2 125.4(2) . . ? O3 C3 C4 115.3(2) . . ? C2 C3 C4 119.2(2) . . ? C4 C5 C6 122.1(2) . . ? C6 C1 C2 119.7(2) . . ? C6 C1 C16 121.4(2) . . ? C2 C1 C16 118.8(2) . . ? O4 C4 C5 125.5(2) . . ? O4 C4 C3 115.4(2) . . ? C5 C4 C3 119.1(2) . . ? O2 C16 N1 111.84(18) . . ? O2 C16 C15 108.93(18) . . ? N1 C16 C15 100.95(17) . . ? O2 C16 C1 110.48(17) . . ? N1 C16 C1 108.35(17) . . ? C15 C16 C1 115.99(19) . . ? C14 C15 C10 120.1(2) . . ? C14 C15 C16 130.3(2) . . ? C10 C15 C16 109.5(2) . . ? C6 C7 C8 111.96(19) . . ? C11 C10 C15 121.6(2) . . ? C11 C10 C9 129.7(2) . . ? C15 C10 C9 108.7(2) . . ? O1 C9 N1 125.7(2) . . ? O1 C9 C10 128.1(2) . . ? N1 C9 C10 106.23(19) . . ? C10 C11 C12 117.9(2) . . ? C13 C12 C11 121.0(2) . . ? C15 C14 C13 118.5(2) . . ? C12 C13 C14 120.9(3) . . ? _diffrn_measured_fraction_theta_max 0.996 _diffrn_reflns_theta_full 25.85 _diffrn_measured_fraction_theta_full 0.996 _refine_diff_density_max 0.190 _refine_diff_density_min -0.169 _refine_diff_density_rms 0.040 # Attachment '- 3a-epu103_m-768897.cif' data_epu103_m _database_code_depnum_ccdc_archive 'CCDC 768897' #TrackingRef '- 3a-epu103_m-768897.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; 12b-Hydroxy-1,3-dimethoxy-5,12b-dihydro-6H-isoindolo[1,2-a]isoquinolin-8-one ; _chemical_name_common ;12b-Hydroxy-1,3-dimethoxy-5,12b-dihydro-6H-isoindolo(1,2- a)isoquinolin-8-one ; _chemical_melting_point 441 _chemical_formula_moiety 'C18 H17 N O4' _chemical_formula_sum 'C18 H17 N O4' _chemical_formula_weight 311.33 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 11.202(5) _cell_length_b 6.303(3) _cell_length_c 21.577(10) _cell_angle_alpha 90.00 _cell_angle_beta 103.609(7) _cell_angle_gamma 90.00 _cell_volume 1480.6(12) _cell_formula_units_Z 4 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used 4203 _cell_measurement_theta_min 2.36 _cell_measurement_theta_max 25.60 _exptl_crystal_description plate _exptl_crystal_colour colorless _exptl_crystal_size_max 0.42 _exptl_crystal_size_mid 0.24 _exptl_crystal_size_min 0.12 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.397 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 656 _exptl_absorpt_coefficient_mu 0.099 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.9595 _exptl_absorpt_correction_T_max 0.9882 _exptl_absorpt_process_details sadabs _exptl_special_details ; ? ; _diffrn_ambient_temperature 293(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type '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 14321 _diffrn_reflns_av_R_equivalents 0.0642 _diffrn_reflns_av_sigmaI/netI 0.0528 _diffrn_reflns_limit_h_min -13 _diffrn_reflns_limit_h_max 13 _diffrn_reflns_limit_k_min -7 _diffrn_reflns_limit_k_max 7 _diffrn_reflns_limit_l_min -26 _diffrn_reflns_limit_l_max 26 _diffrn_reflns_theta_min 1.87 _diffrn_reflns_theta_max 26.01 _reflns_number_total 2902 _reflns_number_gt 2100 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'Bruker SMART' _computing_data_reduction 'Bruker SAINT' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'ORTEP3 (Farrugia, 1997) and Mercury (Bruno et al., 2002)' _computing_publication_material 'SHELXL-97 (Sheldrick, 1997)' _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^)+(0.0968P)^2^+1.2570P] 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 2902 _refine_ls_number_parameters 208 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0962 _refine_ls_R_factor_gt 0.0716 _refine_ls_wR_factor_ref 0.2052 _refine_ls_wR_factor_gt 0.1904 _refine_ls_goodness_of_fit_ref 1.072 _refine_ls_restrained_S_all 1.072 _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 O2 O 0.79737(19) 0.1930(3) 0.13352(11) 0.0430(6) Uani 1 1 d . . . H2 H 0.7691 0.3031 0.1444 0.065 Uiso 1 1 calc R . . O3 O 0.6597(2) 0.2981(4) 0.23249(11) 0.0510(7) Uani 1 1 d . . . N1 N 0.7697(2) -0.1747(4) 0.11994(12) 0.0350(6) Uani 1 1 d . . . C16 C 0.7317(3) 0.0178(4) 0.14943(14) 0.0314(7) Uani 1 1 d . . . O1 O 0.6848(2) -0.4684(3) 0.06490(11) 0.0519(7) Uani 1 1 d . . . C10 C 0.5644(3) -0.1675(5) 0.08407(13) 0.0347(7) Uani 1 1 d . . . C6 C 0.8459(3) -0.1739(4) 0.25012(14) 0.0339(7) Uani 1 1 d . . . C9 C 0.6758(3) -0.2914(5) 0.08766(14) 0.0361(7) Uani 1 1 d . . . C14 C 0.5077(3) 0.1790(5) 0.11262(15) 0.0395(7) Uani 1 1 d . . . H14 H 0.5275 0.3086 0.1330 0.047 Uiso 1 1 calc R . . C5 C 0.8820(3) -0.1915(5) 0.31595(15) 0.0419(8) Uani 1 1 d . . . H5 H 0.9346 -0.3004 0.3342 0.050 Uiso 1 1 calc R . . C4 C 0.8408(3) -0.0502(6) 0.35431(15) 0.0443(8) Uani 1 1 d . . . C15 C 0.5951(3) 0.0209(4) 0.11751(13) 0.0316(7) Uani 1 1 d . . . C2 C 0.7305(3) 0.1360(5) 0.26229(15) 0.0373(7) Uani 1 1 d . . . C1 C 0.7675(2) -0.0110(4) 0.22175(14) 0.0312(7) Uani 1 1 d . . . O4 O 0.8716(2) -0.0537(5) 0.41931(11) 0.0635(8) Uani 1 1 d . . . C8 C 0.8916(3) -0.2559(5) 0.14501(16) 0.0419(8) Uani 1 1 d . . . H8A H 0.9519 -0.1457 0.1447 0.050 Uiso 1 1 calc R . . H8B H 0.9078 -0.3730 0.1190 0.050 Uiso 1 1 calc R . . C13 C 0.3911(3) 0.1403(6) 0.07701(15) 0.0457(8) Uani 1 1 d . . . H13 H 0.3319 0.2461 0.0732 0.055 Uiso 1 1 calc R . . C7 C 0.9002(3) -0.3301(5) 0.21216(16) 0.0451(8) Uani 1 1 d . . . H7A H 0.8576 -0.4646 0.2110 0.054 Uiso 1 1 calc R . . H7B H 0.9858 -0.3532 0.2331 0.054 Uiso 1 1 calc R . . C3 C 0.7646(3) 0.1171(6) 0.32747(15) 0.0452(8) Uani 1 1 d . . . H3 H 0.7373 0.2147 0.3534 0.054 Uiso 1 1 calc R . . C11 C 0.4469(3) -0.2086(5) 0.04925(15) 0.0437(8) Uani 1 1 d . . . H11 H 0.4272 -0.3372 0.0282 0.052 Uiso 1 1 calc R . . C12 C 0.3594(3) -0.0523(6) 0.04665(16) 0.0500(9) Uani 1 1 d . . . H12 H 0.2787 -0.0765 0.0244 0.060 Uiso 1 1 calc R . . C17 C 0.6092(4) 0.4437(6) 0.2700(2) 0.0621(11) Uani 1 1 d . . . H17A H 0.5616 0.5488 0.2428 0.093 Uiso 1 1 calc R . . H17B H 0.6745 0.5118 0.3003 0.093 Uiso 1 1 calc R . . H17C H 0.5574 0.3685 0.2923 0.093 Uiso 1 1 calc R . . C18 C 0.9457(4) -0.2273(8) 0.44924(19) 0.0776(14) Uani 1 1 d . . . H18A H 0.9614 -0.2123 0.4947 0.116 Uiso 1 1 calc R . . H18B H 1.0221 -0.2276 0.4364 0.116 Uiso 1 1 calc R . . H18C H 0.9032 -0.3583 0.4366 0.116 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 O2 0.0394(12) 0.0267(11) 0.0642(15) 0.0024(10) 0.0149(11) -0.0041(9) O3 0.0543(14) 0.0423(13) 0.0537(14) -0.0122(11) 0.0073(11) 0.0201(11) N1 0.0355(14) 0.0285(13) 0.0397(14) -0.0070(10) 0.0061(11) 0.0054(11) C16 0.0316(15) 0.0188(13) 0.0441(17) -0.0029(11) 0.0097(13) 0.0008(11) O1 0.0702(17) 0.0255(12) 0.0515(14) -0.0085(10) -0.0029(12) 0.0061(11) C10 0.0386(16) 0.0320(15) 0.0328(16) 0.0035(12) 0.0069(13) -0.0030(13) C6 0.0298(15) 0.0266(15) 0.0424(17) -0.0003(12) 0.0025(12) -0.0015(12) C9 0.0479(18) 0.0271(16) 0.0306(15) -0.0003(12) 0.0040(13) -0.0031(13) C14 0.0352(16) 0.0390(17) 0.0442(18) 0.0025(14) 0.0092(14) 0.0061(14) C5 0.0364(17) 0.0378(17) 0.0484(19) 0.0027(14) 0.0033(14) -0.0019(14) C4 0.0378(18) 0.054(2) 0.0382(18) -0.0016(15) 0.0042(14) -0.0134(15) C15 0.0319(15) 0.0291(15) 0.0335(15) 0.0030(11) 0.0074(12) -0.0006(12) C2 0.0300(15) 0.0342(16) 0.0471(19) -0.0064(13) 0.0080(13) -0.0003(13) C1 0.0249(14) 0.0275(15) 0.0404(17) -0.0049(12) 0.0060(12) -0.0027(11) O4 0.0645(17) 0.0815(19) 0.0416(14) -0.0005(13) 0.0065(12) -0.0082(15) C8 0.0336(16) 0.0362(17) 0.055(2) -0.0076(14) 0.0085(14) 0.0081(13) C13 0.0340(17) 0.058(2) 0.0446(19) 0.0110(16) 0.0087(14) 0.0086(15) C7 0.0418(18) 0.0323(17) 0.056(2) -0.0039(14) 0.0009(15) 0.0117(14) C3 0.0380(17) 0.053(2) 0.0453(19) -0.0152(15) 0.0116(15) -0.0032(15) C11 0.0446(19) 0.0450(19) 0.0387(18) 0.0009(14) 0.0041(14) -0.0088(15) C12 0.0335(18) 0.070(2) 0.0415(19) 0.0065(17) -0.0008(14) -0.0079(17) C17 0.064(3) 0.045(2) 0.081(3) -0.0203(19) 0.024(2) 0.0107(18) C18 0.076(3) 0.100(4) 0.049(2) 0.023(2) 0.000(2) -0.002(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 O2 C16 1.413(3) . ? O3 C2 1.359(4) . ? O3 C17 1.426(4) . ? N1 C9 1.337(4) . ? N1 C8 1.440(4) . ? N1 C16 1.478(3) . ? C16 C15 1.523(4) . ? C16 C1 1.528(4) . ? O1 C9 1.233(4) . ? C10 C11 1.378(4) . ? C10 C15 1.390(4) . ? C10 C9 1.458(4) . ? C6 C5 1.387(4) . ? C6 C1 1.396(4) . ? C6 C7 1.498(4) . ? C14 C13 1.372(4) . ? C14 C15 1.384(4) . ? C5 C4 1.368(5) . ? C4 O4 1.363(4) . ? C4 C3 1.394(5) . ? C2 C3 1.373(4) . ? C2 C1 1.402(4) . ? O4 C18 1.432(5) . ? C8 C7 1.504(5) . ? C13 C12 1.386(5) . ? C11 C12 1.382(5) . ? 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 O3 C17 118.7(3) . . ? C9 N1 C8 124.1(3) . . ? C9 N1 C16 113.9(2) . . ? C8 N1 C16 118.3(2) . . ? O2 C16 N1 108.5(2) . . ? O2 C16 C15 113.9(2) . . ? N1 C16 C15 100.2(2) . . ? O2 C16 C1 108.3(2) . . ? N1 C16 C1 108.0(2) . . ? C15 C16 C1 117.2(2) . . ? C11 C10 C15 122.1(3) . . ? C11 C10 C9 128.6(3) . . ? C15 C10 C9 109.0(3) . . ? C5 C6 C1 120.6(3) . . ? C5 C6 C7 116.7(3) . . ? C1 C6 C7 122.6(3) . . ? O1 C9 N1 125.2(3) . . ? O1 C9 C10 127.8(3) . . ? N1 C9 C10 106.9(2) . . ? C13 C14 C15 118.6(3) . . ? C4 C5 C6 120.6(3) . . ? O4 C4 C5 124.9(3) . . ? O4 C4 C3 114.9(3) . . ? C5 C4 C3 120.1(3) . . ? C14 C15 C10 119.4(3) . . ? C14 C15 C16 131.4(3) . . ? C10 C15 C16 108.9(2) . . ? O3 C2 C3 122.8(3) . . ? O3 C2 C1 115.3(3) . . ? C3 C2 C1 122.0(3) . . ? C6 C1 C2 117.4(3) . . ? C6 C1 C16 121.5(2) . . ? C2 C1 C16 120.9(3) . . ? C4 O4 C18 117.1(3) . . ? N1 C8 C7 108.2(3) . . ? C14 C13 C12 121.6(3) . . ? C6 C7 C8 112.3(3) . . ? C2 C3 C4 119.1(3) . . ? C10 C11 C12 117.8(3) . . ? C11 C12 C13 120.3(3) . . ? _diffrn_measured_fraction_theta_max 0.995 _diffrn_reflns_theta_full 26.01 _diffrn_measured_fraction_theta_full 0.995 _refine_diff_density_max 0.347 _refine_diff_density_min -0.462 _refine_diff_density_rms 0.061 # Attachment '- 3e-js11-768898.cif' data_js11 _database_code_depnum_ccdc_archive 'CCDC 768898' #TrackingRef '- 3e-js11-768898.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; 12b-Hydroxy-3-methoxy-5,12b-dihydro-6H-isoindolo[1,2-a]isoquinolin-8-one ; _chemical_name_common ;12b-Hydroxy-3-methoxy-5,12b-dihydro-6H-isoindolo(1,2- a)isoquinolin-8-one ; _chemical_melting_point 440 _chemical_formula_moiety 'C17 H15 N O3' _chemical_formula_sum 'C17 H15 N O3' _chemical_formula_weight 281.30 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 11.6208(6) _cell_length_b 16.2041(8) _cell_length_c 7.1495(3) _cell_angle_alpha 90.00 _cell_angle_beta 97.481(3) _cell_angle_gamma 90.00 _cell_volume 1334.82(11) _cell_formula_units_Z 4 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used 4602 _cell_measurement_theta_min 2.51 _cell_measurement_theta_max 30.24 _exptl_crystal_description block _exptl_crystal_colour colorless _exptl_crystal_size_max 0.28 _exptl_crystal_size_mid 0.20 _exptl_crystal_size_min 0.18 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.400 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 592 _exptl_absorpt_coefficient_mu 0.096 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.9735 _exptl_absorpt_correction_T_max 0.9828 _exptl_absorpt_process_details 'SADABS (Bruker 1999)' _exptl_special_details ; ? ; _diffrn_ambient_temperature 293(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Bruker AXS Kappa Apex2 CCD Diffractometer' _diffrn_measurement_method '\w and \f scan' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 19023 _diffrn_reflns_av_R_equivalents 0.0356 _diffrn_reflns_av_sigmaI/netI 0.0343 _diffrn_reflns_limit_h_min -17 _diffrn_reflns_limit_h_max 16 _diffrn_reflns_limit_k_min -23 _diffrn_reflns_limit_k_max 23 _diffrn_reflns_limit_l_min -10 _diffrn_reflns_limit_l_max 9 _diffrn_reflns_theta_min 2.17 _diffrn_reflns_theta_max 31.66 _reflns_number_total 4491 _reflns_number_gt 2916 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'APEX2 (Bruker, 2004)' _computing_cell_refinement 'APEX2/SAINT (Bruker, 2004)' _computing_data_reduction 'SAINT/XPREP (Bruker, 2004)' _computing_structure_solution 'SHELXL-97 (Sheldrick, 1997)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'ORTEP3 (Farrugia, 1997) and Mercury (Bruno et al., 2002)' _computing_publication_material 'SHELXL-97 (Sheldrick, 1997)' _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^)+(0.0642P)^2^+0.1852P] 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 4491 _refine_ls_number_parameters 190 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0844 _refine_ls_R_factor_gt 0.0501 _refine_ls_wR_factor_ref 0.1406 _refine_ls_wR_factor_gt 0.1225 _refine_ls_goodness_of_fit_ref 1.023 _refine_ls_restrained_S_all 1.023 _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 O2 O 0.17766(9) 0.13257(6) -0.00083(13) 0.0438(3) Uani 1 1 d . . . H2 H 0.1352 0.1183 0.0764 0.066 Uiso 1 1 calc R . . O1 O -0.00202(10) -0.09941(6) -0.21955(15) 0.0477(3) Uani 1 1 d . . . C16 C 0.14091(12) 0.09414(7) -0.17597(18) 0.0353(3) Uani 1 1 d . . . N1 N 0.13071(10) 0.00364(6) -0.15437(15) 0.0367(3) Uani 1 1 d . . . C15 C 0.01784(12) 0.11626(8) -0.25342(18) 0.0364(3) Uani 1 1 d . . . C1 C 0.23366(12) 0.10978(7) -0.30041(18) 0.0349(3) Uani 1 1 d . . . C6 C 0.33591(13) 0.06405(8) -0.26117(18) 0.0387(3) Uani 1 1 d . . . C9 C 0.02444(12) -0.02604(8) -0.21770(17) 0.0366(3) Uani 1 1 d . . . C8 C 0.23267(13) -0.04899(8) -0.1180(2) 0.0412(3) Uani 1 1 d . . . H8A H 0.2328 -0.0886 -0.2197 0.049 Uiso 1 1 calc R . . H8B H 0.2301 -0.0793 -0.0016 0.049 Uiso 1 1 calc R . . C2 C 0.22183(13) 0.16415(8) -0.45091(18) 0.0384(3) Uani 1 1 d . . . H2A H 0.1535 0.1942 -0.4782 0.046 Uiso 1 1 calc R . . C3 C 0.30999(13) 0.17457(8) -0.56157(19) 0.0421(3) Uani 1 1 d . . . H3 H 0.3010 0.2112 -0.6626 0.051 Uiso 1 1 calc R . . C10 C -0.04915(13) 0.04553(8) -0.27883(17) 0.0369(3) Uani 1 1 d . . . O3 O 0.50426(11) 0.13594(8) -0.61933(18) 0.0613(3) Uani 1 1 d . . . C4 C 0.41108(13) 0.13019(9) -0.5207(2) 0.0427(3) Uani 1 1 d . . . C5 C 0.42363(13) 0.07462(9) -0.3702(2) 0.0442(3) Uani 1 1 d . . . H5 H 0.4920 0.0445 -0.3437 0.053 Uiso 1 1 calc R . . C7 C 0.34270(13) 0.00229(9) -0.1025(2) 0.0441(3) Uani 1 1 d . . . H7A H 0.3532 0.0310 0.0175 0.053 Uiso 1 1 calc R . . H7B H 0.4090 -0.0336 -0.1073 0.053 Uiso 1 1 calc R . . C11 C -0.16583(14) 0.04855(10) -0.3460(2) 0.0457(3) Uani 1 1 d . . . H11 H -0.2100 0.0007 -0.3634 0.055 Uiso 1 1 calc R . . C14 C -0.03222(14) 0.19288(9) -0.2886(2) 0.0459(4) Uani 1 1 d . . . H14 H 0.0114 0.2409 -0.2669 0.055 Uiso 1 1 calc R . . C12 C -0.21459(15) 0.12517(11) -0.3863(2) 0.0528(4) Uani 1 1 d . . . H12 H -0.2928 0.1291 -0.4339 0.063 Uiso 1 1 calc R . . C13 C -0.14850(15) 0.19632(10) -0.3567(2) 0.0524(4) Uani 1 1 d . . . H13 H -0.1834 0.2474 -0.3834 0.063 Uiso 1 1 calc R . . C17 C 0.49743(19) 0.19503(12) -0.7672(3) 0.0709(6) Uani 1 1 d . . . H17A H 0.5675 0.1934 -0.8250 0.106 Uiso 1 1 calc R . . H17B H 0.4878 0.2491 -0.7167 0.106 Uiso 1 1 calc R . . H17C H 0.4324 0.1825 -0.8599 0.106 Uiso 1 1 calc R . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 O2 0.0559(6) 0.0359(5) 0.0374(5) -0.0083(4) -0.0021(4) -0.0088(4) O1 0.0623(7) 0.0273(5) 0.0533(6) -0.0064(4) 0.0063(5) -0.0089(5) C16 0.0435(8) 0.0226(5) 0.0372(6) -0.0017(4) -0.0044(5) -0.0024(5) N1 0.0453(7) 0.0234(5) 0.0391(5) 0.0003(4) -0.0032(5) 0.0000(4) C15 0.0433(8) 0.0299(6) 0.0348(6) -0.0014(5) 0.0001(5) 0.0004(5) C1 0.0405(7) 0.0251(5) 0.0364(6) -0.0013(4) -0.0054(5) -0.0021(5) C6 0.0435(8) 0.0323(6) 0.0374(6) 0.0049(5) -0.0055(6) 0.0004(6) C9 0.0495(8) 0.0285(6) 0.0312(6) -0.0049(4) 0.0030(5) -0.0047(6) C8 0.0533(9) 0.0293(6) 0.0395(7) 0.0055(5) 0.0005(6) 0.0060(6) C2 0.0437(8) 0.0272(6) 0.0407(7) 0.0029(5) -0.0077(6) 0.0020(5) C3 0.0497(9) 0.0337(6) 0.0401(7) 0.0079(5) -0.0050(6) -0.0017(6) C10 0.0444(8) 0.0326(6) 0.0324(6) -0.0040(5) -0.0005(5) -0.0021(5) O3 0.0553(7) 0.0629(8) 0.0673(8) 0.0252(6) 0.0138(6) 0.0086(6) C4 0.0441(8) 0.0387(7) 0.0437(7) 0.0054(6) -0.0001(6) -0.0017(6) C5 0.0411(8) 0.0407(7) 0.0483(7) 0.0088(6) -0.0038(6) 0.0050(6) C7 0.0471(8) 0.0417(7) 0.0408(7) 0.0092(6) -0.0050(6) 0.0052(6) C11 0.0464(8) 0.0497(8) 0.0390(7) -0.0055(6) -0.0015(6) -0.0051(7) C14 0.0541(9) 0.0314(6) 0.0513(8) 0.0016(6) 0.0040(7) 0.0038(6) C12 0.0451(9) 0.0657(10) 0.0453(8) 0.0018(7) -0.0031(7) 0.0070(8) C13 0.0561(10) 0.0478(8) 0.0526(9) 0.0076(7) 0.0044(7) 0.0171(8) C17 0.0813(14) 0.0640(12) 0.0720(12) 0.0271(10) 0.0268(10) 0.0089(11) _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 O2 C16 1.4138(15) . ? O1 C9 1.2277(15) . ? C16 N1 1.4809(16) . ? C16 C1 1.506(2) . ? C16 C15 1.5081(19) . ? N1 C9 1.3476(17) . ? N1 C8 1.4555(18) . ? C15 C14 1.3802(18) . ? C15 C10 1.3841(18) . ? C1 C2 1.3836(17) . ? C1 C6 1.3975(19) . ? C6 C5 1.372(2) . ? C6 C7 1.5072(18) . ? C9 C10 1.4731(19) . ? C8 C7 1.517(2) . ? C2 C3 1.384(2) . ? C3 C4 1.376(2) . ? C10 C11 1.379(2) . ? O3 C4 1.3704(19) . ? O3 C17 1.421(2) . ? C4 C5 1.3957(19) . ? C11 C12 1.380(2) . ? C14 C13 1.377(2) . ? C12 C13 1.386(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 O2 C16 N1 111.28(10) . . ? O2 C16 C1 106.99(11) . . ? N1 C16 C1 107.55(10) . . ? O2 C16 C15 112.53(11) . . ? N1 C16 C15 100.88(10) . . ? C1 C16 C15 117.42(11) . . ? C9 N1 C8 122.69(11) . . ? C9 N1 C16 113.62(11) . . ? C8 N1 C16 121.63(11) . . ? C14 C15 C10 120.29(14) . . ? C14 C15 C16 129.63(13) . . ? C10 C15 C16 109.98(11) . . ? C2 C1 C6 119.31(13) . . ? C2 C1 C16 124.09(13) . . ? C6 C1 C16 116.58(11) . . ? C5 C6 C1 119.65(12) . . ? C5 C6 C7 122.72(13) . . ? C1 C6 C7 117.58(13) . . ? O1 C9 N1 124.51(13) . . ? O1 C9 C10 128.63(13) . . ? N1 C9 C10 106.86(11) . . ? N1 C8 C7 110.55(11) . . ? C1 C2 C3 121.08(13) . . ? C4 C3 C2 119.33(12) . . ? C11 C10 C15 121.81(13) . . ? C11 C10 C9 129.61(13) . . ? C15 C10 C9 108.55(12) . . ? C4 O3 C17 117.23(13) . . ? O3 C4 C3 124.41(13) . . ? O3 C4 C5 115.48(13) . . ? C3 C4 C5 120.11(14) . . ? C6 C5 C4 120.50(14) . . ? C6 C7 C8 110.34(11) . . ? C10 C11 C12 117.58(14) . . ? C13 C14 C15 118.16(14) . . ? C11 C12 C13 120.82(15) . . ? C14 C13 C12 121.27(15) . . ? _diffrn_measured_fraction_theta_max 0.997 _diffrn_reflns_theta_full 31.66 _diffrn_measured_fraction_theta_full 0.997 _refine_diff_density_max 0.249 _refine_diff_density_min -0.211 _refine_diff_density_rms 0.042 # Attachment '- 8a-crr-2-768899.cif' data_crr-2 _database_code_depnum_ccdc_archive 'CCDC 768899' #TrackingRef '- 8a-crr-2-768899.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; 9,11-dimethoxy-1,2,3,6,7,11b-hexahydrobenzo[a]quinolizin-4-one ; _chemical_name_common 9,11-dimethoxy-1,2,3,6,7,11b-hexahydrobenzo(a)quinolizin-4-one _chemical_melting_point 397 _chemical_formula_moiety 'C15 H19 N O3' _chemical_formula_sum 'C15 H19 N O3' _chemical_formula_weight 261.31 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _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 10.2990(5) _cell_length_b 8.4437(4) _cell_length_c 15.6262(7) _cell_angle_alpha 90.00 _cell_angle_beta 95.396(4) _cell_angle_gamma 90.00 _cell_volume 1352.86(11) _cell_formula_units_Z 4 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used 2446 _cell_measurement_theta_min 3.3091 _cell_measurement_theta_max 29.2576 _exptl_crystal_description block _exptl_crystal_colour colorless _exptl_crystal_size_max 0.30 _exptl_crystal_size_mid 0.22 _exptl_crystal_size_min 0.18 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.283 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 560 _exptl_absorpt_coefficient_mu 0.089 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.9738 _exptl_absorpt_correction_T_max 0.9841 _exptl_absorpt_process_details CrysAlisPro _exptl_special_details ; CrysAlisPro, Oxford Diffraction Ltd., Version 1.171.33.55 (release 05-01-2010 CrysAlis171 .NET) (compiled Jan 5 2010,16:28:46) Empirical absorption correction using spherical harmonics, implemented in SCALE3 ABSPACK scaling algorithm. ; _diffrn_ambient_temperature 293(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'Enhance (Mo) X-ray Source' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Xcalibur, Eos' _diffrn_measurement_method '\w scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 5699 _diffrn_reflns_av_R_equivalents 0.0203 _diffrn_reflns_av_sigmaI/netI 0.0435 _diffrn_reflns_limit_h_min -14 _diffrn_reflns_limit_h_max 7 _diffrn_reflns_limit_k_min -11 _diffrn_reflns_limit_k_max 10 _diffrn_reflns_limit_l_min -19 _diffrn_reflns_limit_l_max 21 _diffrn_reflns_theta_min 3.32 _diffrn_reflns_theta_max 29.32 _reflns_number_total 3124 _reflns_number_gt 1845 _reflns_threshold_expression >2sigma(I) _computing_data_collection ; CrysAlisPro, Oxford Diffraction Ltd., Version 1.171.33.55 (release 05-01-2010 CrysAlis171 .NET) (compiled Jan 5 2010,16:28:46) ; _computing_cell_refinement ; CrysAlisPro, Oxford Diffraction Ltd., Version 1.171.33.55 (release 05-01-2010 CrysAlis171 .NET) (compiled Jan 5 2010,16:28:46) ; _computing_data_reduction ; CrysAlisPro, Oxford Diffraction Ltd., Version 1.171.33.55 (release 05-01-2010 CrysAlis171 .NET) (compiled Jan 5 2010,16:28:46) ; _computing_structure_solution 'SHELXL-97 (Sheldrick, 1997)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics ; 'ORTEP3 (Farrugia, 1997) and Mercury (Bruno et al., 2002)' ; _computing_publication_material 'SHELXL-97 (Sheldrick, 1997)' _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^)+(0.0650P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment constr _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 3124 _refine_ls_number_parameters 172 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0903 _refine_ls_R_factor_gt 0.0488 _refine_ls_wR_factor_ref 0.1258 _refine_ls_wR_factor_gt 0.1146 _refine_ls_goodness_of_fit_ref 0.999 _refine_ls_restrained_S_all 0.999 _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 0.02079(14) 0.56112(17) 0.22705(9) 0.0285(3) Uani 1 1 d . . . C9 C -0.07336(14) 0.52222(18) 0.29369(10) 0.0318(4) Uani 1 1 d . . . H9 H -0.0527 0.4154 0.3154 0.038 Uiso 1 1 calc R . . C2 C 0.15560(15) 0.55550(18) 0.25016(9) 0.0316(4) Uani 1 1 d . . . N1 N -0.20946(13) 0.52085(16) 0.25453(9) 0.0390(3) Uani 1 1 d . . . C6 C -0.02043(14) 0.59748(16) 0.14182(10) 0.0297(3) Uani 1 1 d . . . C3 C 0.24614(15) 0.59563(18) 0.19330(10) 0.0354(4) Uani 1 1 d . . . H3 H 0.3350 0.5940 0.2107 0.043 Uiso 1 1 calc R . . O1 O 0.28123(11) 0.68180(15) 0.04872(7) 0.0523(4) Uani 1 1 d . . . C5 C 0.06948(15) 0.63609(18) 0.08428(10) 0.0357(4) Uani 1 1 d . . . H5 H 0.0406 0.6609 0.0277 0.043 Uiso 1 1 calc R . . C4 C 0.20131(15) 0.63802(18) 0.11024(10) 0.0357(4) Uani 1 1 d . . . O2 O 0.19228(10) 0.50611(14) 0.33249(7) 0.0467(3) Uani 1 1 d . . . C11 C -0.16347(15) 0.5851(2) 0.11094(10) 0.0387(4) Uani 1 1 d . . . H11A H -0.2047 0.6879 0.1145 0.046 Uiso 1 1 calc R . . H11B H -0.1734 0.5510 0.0514 0.046 Uiso 1 1 calc R . . C10 C -0.22803(16) 0.4674(2) 0.16582(11) 0.0446(4) Uani 1 1 d . . . H10A H -0.3204 0.4603 0.1472 0.054 Uiso 1 1 calc R . . H10B H -0.1895 0.3635 0.1606 0.054 Uiso 1 1 calc R . . C15 C -0.06079(16) 0.6348(2) 0.37020(11) 0.0452(4) Uani 1 1 d . . . H15A H 0.0251 0.6244 0.4009 0.054 Uiso 1 1 calc R . . H15B H -0.0712 0.7432 0.3502 0.054 Uiso 1 1 calc R . . C14 C -0.16428(17) 0.5963(2) 0.43001(11) 0.0494(5) Uani 1 1 d . . . H14A H -0.1591 0.4855 0.4463 0.059 Uiso 1 1 calc R . . H14B H -0.1511 0.6600 0.4818 0.059 Uiso 1 1 calc R . . C8 C 0.32698(17) 0.5040(3) 0.36112(13) 0.0616(6) Uani 1 1 d . . . H8A H 0.3384 0.4676 0.4196 0.092 Uiso 1 1 calc R . . H8B H 0.3620 0.6089 0.3578 0.092 Uiso 1 1 calc R . . H8C H 0.3717 0.4340 0.3254 0.092 Uiso 1 1 calc R . . O3 O -0.42326(14) 0.5729(3) 0.25361(10) 0.1104(7) Uani 1 1 d . . . C12 C -0.31384(18) 0.5722(3) 0.29236(13) 0.0620(6) Uani 1 1 d . . . C13 C -0.29579(19) 0.6318(3) 0.38303(13) 0.0675(6) Uani 1 1 d . . . H13A H -0.3627 0.5854 0.4149 0.081 Uiso 1 1 calc R . . H13B H -0.3088 0.7456 0.3824 0.081 Uiso 1 1 calc R . . C7 C 0.41700(19) 0.6789(3) 0.07101(15) 0.0805(7) Uani 1 1 d . . . H7A H 0.4612 0.7131 0.0228 0.121 Uiso 1 1 calc R . . H7B H 0.4438 0.5731 0.0866 0.121 Uiso 1 1 calc R . . H7C H 0.4386 0.7487 0.1188 0.121 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 0.0230(8) 0.0276(8) 0.0350(9) -0.0027(6) 0.0029(6) 0.0006(6) C9 0.0233(8) 0.0345(8) 0.0373(9) 0.0015(7) 0.0015(6) 0.0001(7) C2 0.0276(8) 0.0340(9) 0.0328(9) -0.0008(6) 0.0003(6) 0.0016(7) N1 0.0258(7) 0.0495(8) 0.0419(8) 0.0029(6) 0.0035(6) -0.0031(6) C6 0.0276(8) 0.0262(8) 0.0347(8) -0.0040(6) 0.0011(6) 0.0028(7) C3 0.0232(8) 0.0434(9) 0.0398(9) -0.0035(7) 0.0036(7) -0.0010(7) O1 0.0374(7) 0.0807(9) 0.0402(7) 0.0034(6) 0.0123(5) -0.0094(7) C5 0.0354(9) 0.0423(9) 0.0291(8) -0.0018(7) 0.0011(7) 0.0023(8) C4 0.0330(9) 0.0396(9) 0.0355(9) -0.0037(7) 0.0086(7) -0.0034(7) O2 0.0253(6) 0.0743(9) 0.0397(7) 0.0129(6) -0.0007(5) 0.0021(6) C11 0.0302(9) 0.0511(10) 0.0340(9) -0.0023(7) -0.0012(7) 0.0048(8) C10 0.0296(9) 0.0506(10) 0.0521(11) -0.0035(8) -0.0043(8) -0.0063(8) C15 0.0379(10) 0.0540(11) 0.0451(10) -0.0116(8) 0.0115(8) -0.0079(8) C14 0.0451(11) 0.0616(11) 0.0435(10) -0.0071(9) 0.0138(8) -0.0081(10) C8 0.0286(9) 0.0989(16) 0.0548(12) 0.0197(11) -0.0086(8) 0.0002(10) O3 0.0267(8) 0.235(2) 0.0698(11) -0.0007(12) 0.0046(7) 0.0162(11) C12 0.0279(10) 0.1053(17) 0.0544(13) 0.0117(11) 0.0129(9) 0.0019(10) C13 0.0439(12) 0.1021(17) 0.0600(14) 0.0025(12) 0.0227(10) 0.0065(12) C7 0.0370(12) 0.139(2) 0.0687(15) 0.0147(14) 0.0203(10) -0.0124(13) _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 C6 1.394(2) . ? C1 C2 1.4021(19) . ? C1 C9 1.524(2) . ? C9 N1 1.4759(19) . ? C9 C15 1.523(2) . ? C2 O2 1.3713(17) . ? C2 C3 1.389(2) . ? N1 C12 1.346(2) . ? N1 C10 1.453(2) . ? C6 C5 1.389(2) . ? C6 C11 1.510(2) . ? C3 C4 1.383(2) . ? O1 C4 1.3737(18) . ? O1 C7 1.409(2) . ? C5 C4 1.380(2) . ? O2 C8 1.4172(19) . ? C11 C10 1.507(2) . ? C15 C14 1.517(2) . ? C14 C13 1.509(2) . ? O3 C12 1.228(2) . ? C12 C13 1.499(3) . ? 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 C6 C1 C2 117.31(13) . . ? C6 C1 C9 122.98(13) . . ? C2 C1 C9 119.67(13) . . ? N1 C9 C15 109.73(13) . . ? N1 C9 C1 111.04(13) . . ? C15 C9 C1 112.91(13) . . ? O2 C2 C3 122.14(14) . . ? O2 C2 C1 115.51(13) . . ? C3 C2 C1 122.34(14) . . ? C12 N1 C10 118.68(15) . . ? C12 N1 C9 125.59(15) . . ? C10 N1 C9 115.63(13) . . ? C5 C6 C1 120.58(14) . . ? C5 C6 C11 119.95(13) . . ? C1 C6 C11 119.37(13) . . ? C4 C3 C2 118.58(14) . . ? C4 O1 C7 117.93(14) . . ? C4 C5 C6 120.65(14) . . ? O1 C4 C5 115.79(14) . . ? O1 C4 C3 123.87(14) . . ? C5 C4 C3 120.34(14) . . ? C2 O2 C8 118.36(13) . . ? C10 C11 C6 109.46(13) . . ? N1 C10 C11 108.23(13) . . ? C14 C15 C9 109.71(14) . . ? C13 C14 C15 107.96(16) . . ? O3 C12 N1 121.24(19) . . ? O3 C12 C13 119.40(17) . . ? N1 C12 C13 119.35(17) . . ? C12 C13 C14 114.78(16) . . ? _diffrn_measured_fraction_theta_max 0.843 _diffrn_reflns_theta_full 25.00 _diffrn_measured_fraction_theta_full 0.998 _refine_diff_density_max 0.227 _refine_diff_density_min -0.232 _refine_diff_density_rms 0.043