# Electronic Supplementary Material (ESI) for Organic & Biomolecular Chemistry # This journal is © The Royal Society of Chemistry 2011 data_publication_text _journal_name_full Org.Biomol.Chem. _journal_coden_cambridge 0177 _publ_contact_author_name 'Chinnasamy Ramaraj Ramanathan' _publ_contact_author_address ;ASSISTANT PROFESSOR, DEPARTMENT OF CHEMISTRY PONDICHERRY UNIVERSITY PUDUCHERRY - 605 014, INDIA ; _publ_contact_author_email crrnath.che@pondiuni.edu.in _publ_contact_author_phone +91-413-2654416 _publ_contact_author_fax +91-413-2655987 loop_ _publ_author_address ;ASSISTANT PROFESSOR, DEPARTMENT OF CHEMISTRY PONDICHERRY UNIVERSITY PUDUCHERRY - 605 014, INDIA ; ;DEPARTMENT OF CHEMISTRY PONDICHERRY UNIVERSITY PUDUCHERRY - 605 014, INDIA ; _publ_author_name C.R.RAMANATHAN data_CRR-63-CRR-228 _database_code_depnum_ccdc_archive 'CCDC 828124' #TrackingRef 'CRR-63-CRR-228.cif' _audit_creation_date 2011-05-12 _audit_creation_method ; Olex2 1.1 (compiled 2011.02.15 svn.r1672, GUI svn.r3494) ; _chemical_name_systematic ; 12b-Hydroxy-3-bromo-5,12b-dihydro-6H-isoindolo[1,2-a]isoquinolin-8-one ; _chemical_name_common ; 12b-Hydroxy-3-bromo-5,12b-dihydro-6H-isoindolo[1,2-a]isoquinolin-8-one ; _chemical_formula_moiety 'C16 H12 Br1 N1 O2' _chemical_formula_sum 'C16 H12 Br1 N1 O2' _exptl_crystal_recrystallization_method 'Ethylacetate, Hexane' _chemical_melting_point 436 _exptl_crystal_description block _exptl_crystal_colour colorless _diffrn_ambient_temperature 298(2) _chemical_formula_weight 330.17 loop_ _atom_type_symbol _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source H 0.00000 0.00000 'International Tables Volume C Table 6.1.1.4 (pp. 500-502)' C 0.00347 0.00161 'International Tables Volume C Table 6.1.1.4 (pp. 500-502)' Br -0.28346 2.55990 'International Tables Volume C Table 6.1.1.4 (pp. 500-502)' O 0.01158 0.00611 'International Tables Volume C Table 6.1.1.4 (pp. 500-502)' N 0.00653 0.00323 'International Tables Volume C Table 6.1.1.4 (pp. 500-502)' _space_group_crystal_system monoclinic _space_group_IT_number 15 _space_group_name_H-M_alt C2/c _space_group_name_Hall '-C 2yc' loop_ _space_group_symop_id _space_group_symop_operation_xyz 1 x,y,z 2 -x,y,-z+1/2 3 -x,-y,-z 4 x,-y,z-1/2 5 x+1/2,y+1/2,z 6 -x+1/2,y+1/2,-z+1/2 7 -x+1/2,-y+1/2,-z 8 x+1/2,-y+1/2,z-1/2 _cell_length_a 23.930(3) _cell_length_b 9.1192(4) _cell_length_c 17.171(2) _cell_angle_alpha 90.0 _cell_angle_beta 134.52(2) _cell_angle_gamma 90.0 _cell_volume 2671.5(13) _cell_formula_units_Z 8 _cell_measurement_temperature 298(2) _cell_measurement_reflns_used 2978 _cell_measurement_theta_min 3.3215 _cell_measurement_theta_max 29.1543 _diffrn_reflns_av_R_equivalents 0.0288 _diffrn_reflns_av_unetI/netI 0.0486 _diffrn_reflns_limit_h_max 20 _diffrn_reflns_limit_h_min -28 _diffrn_reflns_limit_k_max 10 _diffrn_reflns_limit_k_min 0 _diffrn_reflns_limit_l_max 20 _diffrn_reflns_limit_l_min 0 _diffrn_reflns_number 7366 _diffrn_reflns_theta_full 24.9999634556 _exptl_crystal_size_max 0.8 _exptl_crystal_size_mid 0.6 _exptl_crystal_size_min 0.45 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn ? _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1328 _exptl_absorpt_coefficient_mu ? _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.61573 _exptl_absorpt_correction_T_max 1.00000 _exptl_absorpt_process_details CrysAlisPro _diffrn_measured_fraction_theta_full 0.989796 _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_radiation_probe ? _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type 'Mo K\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_reflns_av_sigmaI/netI 0.0770 _diffrn_reflns_theta_max 29.1543 _diffrn_reflns_theta_min 3.3215 _reflns_number_gt 1868 _reflns_number_total 2328 _reflns_threshold_expression I>2u(I) _computing_molecular_graphics ; O. V. Dolomanov, L. J. Bourhis, R. J. Gildea, J. A. K. Howard and H. Puschmann, OLEX2: a complete structure solution, refinement and analysis program. J. Appl. Cryst. (2009). 42, 339-341. ; _computing_publication_material ; O. V. Dolomanov, L. J. Bourhis, R. J. Gildea, J. A. K. Howard and H. Puschmann, OLEX2: a complete structure solution, refinement and analysis program. J. Appl. Cryst. (2009). 42, 339-341. ; _computing_structure_solution 'smtbx-flip (Bourhis, 2008)' _refine_diff_density_max 0.477479 _refine_diff_density_min -0.657691 _refine_diff_density_rms 0.097830 _refine_ls_d_res_high 0.840866 _refine_ls_d_res_low 6.121043 _refine_ls_goodness_of_fit_ref 1.025330 _refine_ls_matrix_type full _refine_ls_hydrogen_treatment mixed _refine_ls_number_constraints 20 _refine_ls_number_parameters 186 _refine_ls_number_reflns 2328 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.053107 _refine_ls_R_factor_gt 0.039394 _refine_ls_restrained_S_all 1.025330 _refine_ls_shift/su_max 0.0039 _refine_ls_shift/su_mean 0.0002 _refine_ls_structure_factor_coef Fsqd _refine_ls_weighting_details 'w=1/[\s^2^(Fo^2^)+(0.0404P)^2^+3.9665P] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_ref 0.065956 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 Br Br 0.31934(2) 0.64320(4) 0.65091(3) 0.05692(18) Uani 1.000000 O2 O 0.42405(13) 0.2899(2) 0.43537(17) 0.0341(5) Uani 1.000000 O3 O 0.51498(14) -0.1293(2) 0.62880(19) 0.0389(6) Uani 1.000000 C4 C 0.6034(2) 0.3472(3) 0.6422(3) 0.0345(8) Uani 1.000000 C5 C 0.58081(18) 0.0983(3) 0.6576(2) 0.0281(7) Uani 1.000000 N N 0.44896(14) 0.0854(3) 0.5427(2) 0.0292(6) Uani 1.000000 C7 C 0.51402(18) 0.0020(3) 0.6115(2) 0.0290(7) Uani 1.000000 C8 C 0.43342(18) 0.3354(3) 0.5777(2) 0.0283(7) Uani 1.000000 C9 C 0.3537(2) 0.3694(3) 0.6139(3) 0.0359(8) Uani 1.000000 C10 C 0.65933(19) 0.0635(4) 0.7283(3) 0.0383(8) Uani 1.000000 C11 C 0.38692(18) 0.2762(3) 0.5915(2) 0.0302(7) Uani 1.000000 C12 C 0.36752(19) 0.5188(4) 0.6235(3) 0.0367(8) Uani 1.000000 C13 C 0.3699(2) 0.1131(3) 0.5794(3) 0.0386(8) Uani 1.000000 C14 C 0.55287(17) 0.2384(3) 0.6173(2) 0.0267(7) Uani 1.000000 C15 C 0.7108(2) 0.1727(4) 0.7552(3) 0.0433(9) Uani 1.000000 C16 C 0.4144(2) 0.5784(4) 0.6126(3) 0.0405(8) Uani 1.000000 C17 C 0.6824(2) 0.3111(4) 0.7114(3) 0.0428(9) Uani 1.000000 C18 C 0.46464(17) 0.2414(3) 0.5422(2) 0.0273(7) Uani 1.000000 C19 C 0.4471(2) 0.4864(3) 0.5898(3) 0.0379(8) Uani 1.000000 C20 C 0.37484(18) 0.0440(3) 0.5045(3) 0.0337(8) Uani 1.000000 H2 H 0.4428(19) 0.244(4) 0.417(3) -0.000(9) Uiso 1.000000 H16 H 0.4240(2) 0.6788(4) 0.6205(3) 0.0485(10) Uiso 1.000000 H19 H 0.4790(2) 0.5257(3) 0.5823(3) 0.0455(10) Uiso 1.000000 H9 H 0.3223(2) 0.3314(3) 0.6225(3) 0.0430(9) Uiso 1.000000 H10 H 0.67720(19) -0.0305(4) 0.7571(3) 0.0460(10) Uiso 1.000000 H15 H 0.7641(2) 0.1528(4) 0.8025(3) 0.0519(11) Uiso 1.000000 H17 H 0.7172(2) 0.3829(4) 0.7286(3) 0.0514(10) Uiso 1.000000 H4 H 0.5854(2) 0.4413(3) 0.6139(3) 0.0415(9) Uiso 1.000000 H13a H 0.4077(13) 0.0668(10) 0.6506(4) 0.0463(10) Uiso 1.000000 H13b H 0.3177(7) 0.0985(17) 0.549(2) 0.0463(10) Uiso 1.000000 H20a H 0.3320(5) 0.078(3) 0.4304(7) 0.0405(9) Uiso 1.000000 H20b H 0.3717(13) -0.0619(3) 0.506(2) 0.0405(9) Uiso 1.000000 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 Br 0.0626(3) 0.0486(3) 0.0698(3) 0.00226(19) 0.0501(3) -0.01295(19) O2 0.0368(14) 0.0356(12) 0.0285(12) 0.0097(11) 0.0224(11) 0.0067(10) O3 0.0426(15) 0.0250(12) 0.0542(14) 0.0043(10) 0.0358(13) 0.0083(10) C4 0.035(2) 0.0319(17) 0.0377(18) -0.0063(15) 0.0259(17) -0.0024(14) C5 0.0269(18) 0.0292(16) 0.0295(16) 0.0005(14) 0.0202(15) 0.0003(13) N 0.0246(15) 0.0227(12) 0.0346(14) -0.0026(11) 0.0186(13) -0.0007(11) C7 0.0311(19) 0.0277(17) 0.0340(17) 0.0022(14) 0.0249(16) 0.0002(14) C8 0.0259(18) 0.0272(16) 0.0252(16) 0.0026(13) 0.0155(14) 0.0031(13) C9 0.034(2) 0.0395(19) 0.0361(18) -0.0016(15) 0.0250(17) -0.0025(15) C10 0.032(2) 0.0379(19) 0.0441(19) 0.0040(16) 0.0261(17) 0.0005(16) C11 0.0283(18) 0.0290(16) 0.0275(16) -0.0003(14) 0.0174(15) 0.0010(13) C12 0.034(2) 0.0389(18) 0.0359(18) 0.0048(16) 0.0241(16) -0.0006(15) C13 0.038(2) 0.0322(17) 0.052(2) -0.0051(15) 0.0343(19) 0.0004(15) C14 0.0268(18) 0.0290(16) 0.0231(15) -0.0022(13) 0.0170(14) -0.0019(12) C15 0.0261(19) 0.050(2) 0.048(2) -0.0021(17) 0.0237(17) -0.0065(17) C16 0.046(2) 0.0291(17) 0.043(2) 0.0005(16) 0.0301(18) -0.0012(15) C17 0.034(2) 0.049(2) 0.050(2) -0.0163(17) 0.0309(18) -0.0134(18) C18 0.0250(18) 0.0247(15) 0.0251(16) -0.0004(13) 0.0150(14) 0.0027(12) C19 0.043(2) 0.0308(17) 0.047(2) -0.0022(15) 0.0337(18) 0.0002(15) C20 0.0230(18) 0.0304(17) 0.0383(19) -0.0046(14) 0.0181(16) -0.0033(15) loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 Br C12 1.897(3) . O2 C18 1.416(3) . O3 C7 1.230(3) . C4 C14 1.380(4) . C4 C17 1.394(5) . C5 C7 1.476(4) . C5 C10 1.381(4) . C5 C14 1.382(4) . N C7 1.349(4) . N C18 1.473(4) . N C20 1.445(4) . C8 C11 1.398(4) . C8 C18 1.518(4) . C8 C19 1.397(4) . C9 C11 1.389(4) . C9 C12 1.384(4) . C10 C15 1.387(5) . C11 C13 1.517(4) . C12 C16 1.372(5) . C13 C20 1.509(5) . C14 C18 1.518(4) . C15 C17 1.380(5) . C16 C19 1.378(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 C17 C4 C14 117.7(3) . . C10 C5 C7 129.0(3) . . C14 C5 C7 108.7(3) . . C14 C5 C10 122.4(3) . . C18 N C7 114.1(2) . . C20 N C7 123.0(3) . . C20 N C18 119.1(2) . . C5 C7 O3 128.3(3) . . N C7 O3 125.1(3) . . N C7 C5 106.6(2) . . C18 C8 C11 121.6(3) . . C19 C8 C11 119.2(3) . . C19 C8 C18 119.1(3) . . C12 C9 C11 120.0(3) . . C15 C10 C5 118.1(3) . . C9 C11 C8 119.2(3) . . C13 C11 C8 121.7(3) . . C13 C11 C9 119.1(3) . . C9 C12 Br 118.9(3) . . C16 C12 Br 119.6(2) . . C16 C12 C9 121.5(3) . . C20 C13 C11 110.6(3) . . C5 C14 C4 119.9(3) . . C18 C14 C4 130.2(3) . . C18 C14 C5 109.8(2) . . C17 C15 C10 119.5(3) . . C19 C16 C12 118.7(3) . . C15 C17 C4 122.4(3) . . N C18 O2 111.3(2) . . C8 C18 O2 105.1(2) . . C8 C18 N 110.1(2) . . C14 C18 O2 112.8(2) . . C14 C18 N 100.7(2) . . C14 C18 C8 116.9(2) . . C16 C19 C8 121.4(3) . . C13 C20 N 108.0(3) . . # Attachment 'CRR25.cif' data_crr25 _database_code_depnum_ccdc_archive 'CCDC 828125' #TrackingRef 'CRR25.cif' _audit_creation_date 2011-05-24 _audit_creation_method ; Olex2 1.1 (compiled 2011.02.15 svn.r1672, GUI svn.r3494) ; _chemical_name_common 12b-Hydroxy-5,12b-dihydro-6H-isoindolo[1,2-a]isoquinolin-8-one _chemical_name_systematic ; 12b-Hydroxy-5,12b-dihydro-6H-isoindolo[1,2-a]isoquinolin-8-one ; _chemical_formula_moiety '0.666667(C16 H13 N O2)' _chemical_formula_sum 'C13 H12 N3 O2' _chemical_formula_weight 242.26 _chemical_melting_point 417 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' _space_group_crystal_system triclinic _space_group_IT_number 2 _space_group_name_H-M_alt 'P -1' _space_group_name_Hall '-P 1' loop_ _space_group_symop_id _space_group_symop_operation_xyz 1 'x, y, z' 2 '-x, -y, -z' _cell_length_a 7.9048(8) _cell_length_b 7.9136(11) _cell_length_c 10.4368(15) _cell_angle_alpha 78.413(13) _cell_angle_beta 87.471(10) _cell_angle_gamma 76.970(10) _cell_volume 623.10(14) _cell_formula_units_Z 3 _cell_measurement_reflns_used 2195 _cell_measurement_temperature 293(2) _cell_measurement_theta_max 29.1645 _cell_measurement_theta_min 2.6394 _exptl_absorpt_coefficient_mu 0.135 _exptl_absorpt_correction_T_max 1.00000 _exptl_absorpt_correction_T_min 0.48317 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details ; CrysAlisPro, Oxford Diffraction Ltd., Version 1.171.33.66 (release 28-04-2010 CrysAlis171 .NET) (compiled Apr 28 2010,14:27:37) Empirical absorption correction using spherical harmonics, implemented in SCALE3 ABSPACK scaling algorithm. ; _exptl_crystal_colour colorless _exptl_crystal_density_diffrn 1.937 _exptl_crystal_density_meas ? _exptl_crystal_density_method 'not measured' _exptl_crystal_description ? _exptl_crystal_F_000 381 _exptl_crystal_size_max 0.5 _exptl_crystal_size_mid 0.3 _exptl_crystal_size_min 0.1 _exptl_special_details ; ? ; _diffrn_reflns_av_R_equivalents 0.0318 _diffrn_reflns_av_unetI/netI 0.0534 _diffrn_reflns_limit_h_max 10 _diffrn_reflns_limit_h_min -10 _diffrn_reflns_limit_k_max 9 _diffrn_reflns_limit_k_min -7 _diffrn_reflns_limit_l_max 13 _diffrn_reflns_limit_l_min -14 _diffrn_reflns_number 4341 _diffrn_reflns_theta_full 29.23 _diffrn_reflns_theta_max 29.23 _diffrn_reflns_theta_min 2.64 _diffrn_ambient_temperature 293(2) _diffrn_detector_area_resol_mean 15.9821 _diffrn_measured_fraction_theta_full 0.834 _diffrn_measured_fraction_theta_max 0.834 _diffrn_measurement_device_type 'Xcalibur, Eos' _diffrn_measurement_method '\w scans' _diffrn_radiation_monochromator graphite _diffrn_radiation_type MoK\a _diffrn_radiation_wavelength 0.71073 _diffrn_source 'fine-focus sealed tube' _diffrn_standards_decay_% ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_number ? _reflns_number_gt 1804 _reflns_number_total 2819 _reflns_threshold_expression >2sigma(I) _computing_cell_refinement ; CrysAlisPro, Oxford Diffraction Ltd., Version 1.171.33.66 (release 28-04-2010 CrysAlis171 .NET) (compiled Apr 28 2010,14:27:37) ; _computing_data_collection ; CrysAlisPro, Oxford Diffraction Ltd., Version 1.171.33.66 (release 28-04-2010 CrysAlis171 .NET) (compiled Apr 28 2010,14:27:37) ; _computing_data_reduction ; CrysAlisPro, Oxford Diffraction Ltd., Version 1.171.33.66 (release 28-04-2010 CrysAlis171 .NET) (compiled Apr 28 2010,14:27:37) ; _computing_molecular_graphics ; O. V. Dolomanov, L. J. Bourhis, R. J. Gildea, J. A. K. Howard and H. Puschmann, OLEX2: a complete structure solution, refinement and analysis program. J. Appl. Cryst. (2009). 42, 339-341. ; _computing_publication_material ; O. V. Dolomanov, L. J. Bourhis, R. J. Gildea, J. A. K. Howard and H. Puschmann, OLEX2: a complete structure solution, refinement and analysis program. J. Appl. Cryst. (2009). 42, 339-341. ; _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_structure_solution 'A short history of SHELX (Sheldrick, 2007)' _refine_diff_density_max 0.307 _refine_diff_density_min -0.240 _refine_diff_density_rms 0.052 _refine_ls_extinction_coef ? _refine_ls_extinction_method none _refine_ls_goodness_of_fit_ref 1.044 _refine_ls_hydrogen_treatment mixed _refine_ls_matrix_type full _refine_ls_number_parameters 173 _refine_ls_number_reflns 2819 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.1041 _refine_ls_R_factor_gt 0.0630 _refine_ls_restrained_S_all 1.044 _refine_ls_shift/su_max 0.000 _refine_ls_shift/su_mean 0.000 _refine_ls_structure_factor_coef Fsqd _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.1000P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_gt 0.1558 _refine_ls_wR_factor_ref 0.1769 _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. ; _atom_sites_solution_hydrogens geom _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap 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 0.2993(2) 0.7640(2) 0.40903(14) 0.0404(4) Uani 1 1 d . . . H1 H 0.2957 0.7930 0.4804 0.061 Uiso 1 1 calc R . . O2 O 0.68104(18) 1.1140(2) 0.36132(15) 0.0441(5) Uani 1 1 d . . . C3 C 0.3387(3) 0.8388(3) 0.1822(2) 0.0349(5) Uani 1 1 d . . . C4 C 0.2503(2) 1.0810(3) 0.32064(19) 0.0292(5) Uani 1 1 d . . . N N 0.5286(2) 0.9089(3) 0.33439(17) 0.0361(5) Uani 1 1 d . . . C6 C 0.3660(2) 1.1823(3) 0.33981(19) 0.0302(5) Uani 1 1 d . . . C7 C 0.4898(3) 0.7814(3) 0.1125(2) 0.0415(6) Uani 1 1 d . . . C8 C 0.5438(3) 1.0713(3) 0.34650(19) 0.0324(5) Uani 1 1 d . . . C9 C 0.3094(3) 1.3557(3) 0.3539(2) 0.0389(6) Uani 1 1 d . . . H9 H 0.3880 1.4233 0.3646 0.047 Uiso 1 1 calc R . . C10 C 0.3500(3) 0.8960(3) 0.3121(2) 0.0319(5) Uani 1 1 d . . . C11 C 0.1779(3) 0.8352(3) 0.1371(2) 0.0443(6) Uani 1 1 d . . . H11 H 0.0789 0.8712 0.1849 0.053 Uiso 1 1 calc R . . C12 C 0.0740(3) 1.1492(4) 0.3216(2) 0.0412(6) Uani 1 1 d . . . H12 H -0.0047 1.0809 0.3125 0.049 Uiso 1 1 calc R . . C13 C 0.1337(3) 1.4257(3) 0.3517(2) 0.0467(6) Uani 1 1 d . . . H13 H 0.0921 1.5425 0.3603 0.056 Uiso 1 1 calc R . . C14 C 0.6711(3) 0.7712(4) 0.3043(2) 0.0463(6) Uani 1 1 d . . . H14A H 0.6578 0.6564 0.3520 0.056 Uiso 1 1 calc R . . H14B H 0.7807 0.7909 0.3294 0.056 Uiso 1 1 calc R . . C15 C 0.6684(3) 0.7772(4) 0.1584(2) 0.0494(7) Uani 1 1 d . . . H15A H 0.7062 0.8815 0.1123 0.059 Uiso 1 1 calc R . . H15B H 0.7490 0.6740 0.1380 0.059 Uiso 1 1 calc R . . C16 C 0.4687(4) 0.7261(4) -0.0040(2) 0.0529(7) Uani 1 1 d . . . H16 H 0.5664 0.6892 -0.0529 0.063 Uiso 1 1 calc R . . C17 C 0.3085(4) 0.7247(4) -0.0479(3) 0.0608(8) Uani 1 1 d . . . H17 H 0.2990 0.6867 -0.1255 0.073 Uiso 1 1 calc R . . C18 C 0.0180(3) 1.3228(4) 0.3367(3) 0.0487(7) Uani 1 1 d . . . H18 H -0.1006 1.3719 0.3367 0.058 Uiso 1 1 calc R . . C19 C 0.1621(4) 0.7788(4) 0.0218(3) 0.0558(7) Uani 1 1 d . . . H19 H 0.0534 0.7776 -0.0081 0.067 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 0.0579(10) 0.0254(10) 0.0388(8) -0.0041(7) 0.0044(7) -0.0139(8) O2 0.0316(8) 0.0591(13) 0.0466(9) -0.0151(9) 0.0047(6) -0.0170(8) C3 0.0451(12) 0.0179(12) 0.0377(11) -0.0013(9) -0.0006(9) -0.0027(9) C4 0.0305(10) 0.0216(12) 0.0346(10) -0.0052(9) 0.0021(8) -0.0043(8) N 0.0278(9) 0.0327(12) 0.0449(10) -0.0096(9) 0.0013(7) 0.0009(8) C6 0.0325(10) 0.0269(13) 0.0311(10) -0.0050(9) 0.0043(8) -0.0077(9) C7 0.0568(14) 0.0203(13) 0.0418(12) -0.0026(10) 0.0080(10) -0.0016(11) C8 0.0321(11) 0.0367(15) 0.0289(10) -0.0068(9) 0.0050(8) -0.0091(9) C9 0.0492(13) 0.0233(13) 0.0461(13) -0.0076(10) 0.0031(10) -0.0115(10) C10 0.0317(10) 0.0249(13) 0.0389(11) -0.0063(9) 0.0028(8) -0.0061(9) C11 0.0529(14) 0.0331(16) 0.0472(13) -0.0066(11) -0.0026(10) -0.0106(12) C12 0.0309(11) 0.0343(15) 0.0586(14) -0.0120(11) 0.0018(9) -0.0058(10) C13 0.0583(15) 0.0199(14) 0.0559(15) -0.0058(11) 0.0052(11) 0.0013(11) C14 0.0346(11) 0.0369(16) 0.0606(15) -0.0112(12) 0.0001(10) 0.0073(11) C15 0.0471(14) 0.0357(16) 0.0562(15) -0.0086(12) 0.0152(11) 0.0065(12) C16 0.0809(18) 0.0296(16) 0.0412(13) -0.0043(11) 0.0097(12) -0.0022(13) C17 0.105(2) 0.0375(18) 0.0395(14) -0.0062(12) -0.0087(14) -0.0151(16) C18 0.0353(12) 0.0375(17) 0.0668(16) -0.0126(13) 0.0015(11) 0.0071(11) C19 0.0790(19) 0.0412(18) 0.0485(14) -0.0063(13) -0.0162(13) -0.0149(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 C10 1.415(3) . ? O2 C8 1.231(2) . ? C3 C7 1.405(3) . ? C3 C10 1.525(3) . ? C3 C11 1.383(3) . ? C4 C6 1.389(3) . ? C4 C10 1.516(3) . ? C4 C12 1.377(3) . ? N C8 1.348(3) . ? N C10 1.470(3) . ? N C14 1.452(3) . ? C6 C8 1.476(3) . ? C6 C9 1.380(3) . ? C7 C15 1.502(3) . ? C7 C16 1.401(3) . ? C9 C13 1.374(3) . ? C11 C19 1.385(3) . ? C12 C18 1.384(4) . ? C13 C18 1.387(3) . ? C14 C15 1.515(3) . ? C16 C17 1.368(4) . ? C17 C19 1.371(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 C7 C3 C10 120.7(2) . . ? C11 C3 C7 120.2(2) . . ? C11 C3 C10 119.03(19) . . ? C6 C4 C10 109.45(17) . . ? C12 C4 C6 120.4(2) . . ? C12 C4 C10 129.9(2) . . ? C8 N C10 114.27(18) . . ? C8 N C14 124.58(18) . . ? C14 N C10 118.53(19) . . ? C4 C6 C8 108.74(19) . . ? C9 C6 C4 121.59(19) . . ? C9 C6 C8 129.63(19) . . ? C3 C7 C15 122.7(2) . . ? C16 C7 C3 117.2(2) . . ? C16 C7 C15 120.1(2) . . ? O2 C8 N 125.5(2) . . ? O2 C8 C6 128.1(2) . . ? N C8 C6 106.44(17) . . ? C13 C9 C6 118.1(2) . . ? O1 C10 C3 105.84(18) . . ? O1 C10 C4 112.71(16) . . ? O1 C10 N 111.05(17) . . ? C4 C10 C3 116.25(19) . . ? N C10 C3 110.04(16) . . ? N C10 C4 101.00(17) . . ? C3 C11 C19 121.0(2) . . ? C4 C12 C18 117.7(2) . . ? C9 C13 C18 120.3(2) . . ? N C14 C15 107.9(2) . . ? C7 C15 C14 111.30(17) . . ? C17 C16 C7 121.9(2) . . ? C16 C17 C19 120.4(2) . . ? C12 C18 C13 121.8(2) . . ? C17 C19 C11 119.3(3) . . ? # Attachment 'CRR45.cif' data_crr45 _database_code_depnum_ccdc_archive 'CCDC 828126' #TrackingRef 'CRR45.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; 12b-Hydroxy-1,4-dimethoxy-5,12b-dihydro-6H-isoindolo[1,2-a]isoquinolin-8-one ; _chemical_name_common ; 12b-Hydroxy-1,4-dimethoxy-5,12b-dihydro-6H-isoindolo[1,2-a]isoquinolin-8-one ; _chemical_melting_point 438 _chemical_formula_moiety 'C18 H17 N1 O4' _chemical_formula_sum 'C18 H17 N1 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 orthorhombic _symmetry_space_group_name_H-M 'p n 21 a' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y+1/2, -z' 'x+1/2, y, -z+1/2' '-x+1/2, y+1/2, z+1/2' _cell_length_a 11.3081(6) _cell_length_b 6.5772(4) _cell_length_c 20.0573(13) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 1491.77(15) _cell_formula_units_Z 4 _cell_measurement_temperature 298(2) _cell_measurement_reflns_used 1321 _cell_measurement_theta_min 2.7092 _cell_measurement_theta_max 29.0008 _exptl_crystal_description needle _exptl_crystal_colour colorless _exptl_crystal_size_max 0.4 _exptl_crystal_size_mid 0.3 _exptl_crystal_size_min 0.3 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.386 _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 0.71589 _exptl_absorpt_correction_T_max 1.00000 _exptl_absorpt_process_details CrysalisPro _exptl_special_details ; CrysAlisPro, Oxford Diffraction Ltd., Version 1.171.33.66 (release 28-04-2010 CrysAlis171 .NET) (compiled Apr 28 2010,14:27:37) Empirical absorption correction using spherical harmonics, implemented in SCALE3 ABSPACK scaling algorithm. ; _diffrn_ambient_temperature 298(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type '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 3893 _diffrn_reflns_av_R_equivalents 0.0268 _diffrn_reflns_av_sigmaI/netI 0.0659 _diffrn_reflns_limit_h_min -13 _diffrn_reflns_limit_h_max 7 _diffrn_reflns_limit_k_min -7 _diffrn_reflns_limit_k_max 7 _diffrn_reflns_limit_l_min -20 _diffrn_reflns_limit_l_max 23 _diffrn_reflns_theta_min 2.71 _diffrn_reflns_theta_max 25.00 _reflns_number_total 2189 _reflns_number_gt 1271 _reflns_threshold_expression >2sigma(I) _computing_data_collection ; CrysAlisPro, Oxford Diffraction Ltd., Version 1.171.33.66 (release 28-04-2010 CrysAlis171 .NET) (compiled Apr 28 2010,14:27:37) ; _computing_cell_refinement ; CrysAlisPro, Oxford Diffraction Ltd., Version 1.171.33.66 (release 28-04-2010 CrysAlis171 .NET) (compiled Apr 28 2010,14:27:37) ; _computing_data_reduction ; CrysAlisPro, Oxford Diffraction Ltd., Version 1.171.33.66 (release 28-04-2010 CrysAlis171 .NET) (compiled Apr 28 2010,14:27:37) ; _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics ? _computing_publication_material ? _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^)+(0.0272P)^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 mixed _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881' _refine_ls_abs_structure_Flack 0.3(12) _refine_ls_number_reflns 2189 _refine_ls_number_parameters 211 _refine_ls_number_restraints 1 _refine_ls_R_factor_all 0.0711 _refine_ls_R_factor_gt 0.0337 _refine_ls_wR_factor_ref 0.0620 _refine_ls_wR_factor_gt 0.0569 _refine_ls_goodness_of_fit_ref 0.792 _refine_ls_restrained_S_all 0.792 _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 0.7676(2) 0.1613(5) 0.46827(13) 0.0375(6) Uani 1 1 d . . . O2 O 0.66987(17) 0.4790(3) 0.46252(9) 0.0578(5) Uani 1 1 d . . . N N 0.8143(2) -0.0429(3) 0.37088(11) 0.0490(6) Uani 1 1 d . . . C4 C 0.8183(2) 0.0197(4) 0.57562(16) 0.0515(8) Uani 1 1 d . . . O5 O 0.86825(17) -0.1448(3) 0.60705(10) 0.0707(6) Uani 1 1 d . . . C6 C 0.7157(2) 0.3263(4) 0.50227(14) 0.0433(7) Uani 1 1 d . . . O7 O 0.83729(14) 0.3059(3) 0.36406(11) 0.0653(6) Uani 1 1 d . . . H7 H 0.8000 0.4126 0.3615 0.098 Uiso 1 1 calc R . . C8 C 0.7150(2) 0.3344(5) 0.57071(15) 0.0578(8) Uani 1 1 d . . . H8 H 0.6814 0.4451 0.5925 0.069 Uiso 1 1 calc R . . C9 C 0.8241(2) 0.0121(4) 0.50567(14) 0.0396(7) Uani 1 1 d . . . C10 C 0.6426(2) 0.1444(5) 0.35876(12) 0.0425(7) Uani 1 1 d . . . C11 C 0.7648(2) 0.1538(5) 0.39193(13) 0.0422(6) Uani 1 1 d . . . C12 C 0.7644(2) 0.1780(5) 0.60711(14) 0.0591(8) Uani 1 1 d . . . H12 H 0.7609 0.1807 0.6534 0.071 Uiso 1 1 calc R . . O13 O 0.7591(2) -0.3336(3) 0.31487(9) 0.0839(7) Uani 1 1 d . . . C14 C 0.8971(2) -0.1546(4) 0.47426(12) 0.0510(8) Uani 1 1 d . . . H14A H 0.9712 -0.1679 0.4982 0.061 Uiso 1 1 calc R . . H14B H 0.8550 -0.2827 0.4779 0.061 Uiso 1 1 calc R . . C15 C 0.6276(3) -0.0425(5) 0.32801(13) 0.0514(8) Uani 1 1 d . . . C16 C 0.5945(3) 0.6279(4) 0.49264(15) 0.0745(10) Uani 1 1 d . . . H16A H 0.5626 0.7150 0.4587 0.112 Uiso 1 1 calc R . . H16B H 0.6393 0.7076 0.5238 0.112 Uiso 1 1 calc R . . H16C H 0.5310 0.5608 0.5156 0.112 Uiso 1 1 calc R . . C17 C 0.5549(2) 0.2916(5) 0.35231(13) 0.0584(8) Uani 1 1 d . . . H17 H 0.5640 0.4198 0.3712 0.070 Uiso 1 1 calc R . . C18 C 0.4389(3) 0.0526(7) 0.28941(16) 0.0805(12) Uani 1 1 d . . . H18 H 0.3684 0.0219 0.2678 0.097 Uiso 1 1 calc R . . C19 C 0.7378(3) -0.1611(5) 0.33620(13) 0.0581(8) Uani 1 1 d . . . C20 C 0.8852(2) -0.1351(5) 0.67697(13) 0.0753(10) Uani 1 1 d . . . H20A H 0.9352 -0.0217 0.6876 0.113 Uiso 1 1 calc R . . H20B H 0.9217 -0.2585 0.6921 0.113 Uiso 1 1 calc R . . H20C H 0.8101 -0.1186 0.6986 0.113 Uiso 1 1 calc R . . C21 C 0.9222(2) -0.1105(5) 0.40173(13) 0.0631(9) Uani 1 1 d . . . H21A H 0.9824 -0.0060 0.3980 0.076 Uiso 1 1 calc R . . H21B H 0.9509 -0.2323 0.3797 0.076 Uiso 1 1 calc R . . C22 C 0.4536(3) 0.2416(7) 0.31697(16) 0.0725(10) Uani 1 1 d . . . H22 H 0.3943 0.3384 0.3119 0.087 Uiso 1 1 calc R . . C23 C 0.5262(3) -0.0927(6) 0.29310(14) 0.0709(10) Uani 1 1 d . . . H23 H 0.5175 -0.2192 0.2730 0.085 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 0.0284(14) 0.0361(14) 0.0480(18) -0.0015(16) 0.0040(14) -0.0021(15) O2 0.0658(13) 0.0420(13) 0.0657(14) -0.0036(12) 0.0035(11) 0.0171(12) N 0.0594(16) 0.0436(15) 0.0441(15) 0.0006(12) 0.0061(13) 0.0177(15) C4 0.0451(19) 0.054(2) 0.056(2) -0.0015(18) -0.0105(19) -0.0034(17) O5 0.0887(14) 0.0732(15) 0.0503(14) 0.0057(13) -0.0166(11) 0.0215(14) C6 0.0368(16) 0.0377(18) 0.056(2) -0.0060(19) -0.0015(15) -0.0028(15) O7 0.0468(10) 0.0550(13) 0.0942(16) 0.0243(13) 0.0218(11) 0.0044(11) C8 0.0622(19) 0.056(2) 0.055(2) -0.013(2) 0.0051(17) 0.0058(19) C9 0.0344(16) 0.0377(18) 0.047(2) -0.0023(16) -0.0034(15) 0.0065(14) C10 0.0418(16) 0.0513(18) 0.0343(17) 0.0132(17) 0.0064(13) 0.0041(19) C11 0.0414(16) 0.0346(15) 0.0506(19) 0.0094(16) 0.0097(14) 0.0051(17) C12 0.063(2) 0.071(2) 0.0435(19) -0.004(2) -0.0017(17) 0.004(2) O13 0.151(2) 0.0366(12) 0.0638(14) -0.0018(13) -0.0001(13) 0.0109(17) C14 0.0497(16) 0.0477(18) 0.056(2) 0.0037(17) -0.0048(14) 0.0082(17) C15 0.075(2) 0.048(2) 0.0308(18) 0.0098(16) 0.0016(17) -0.002(2) C16 0.070(2) 0.0484(19) 0.106(3) -0.003(2) 0.0180(19) 0.016(2) C17 0.0518(18) 0.074(2) 0.0492(19) 0.0047(16) 0.0016(16) -0.002(2) C18 0.068(3) 0.132(4) 0.041(2) 0.019(2) -0.0114(19) -0.021(3) C19 0.098(3) 0.0427(19) 0.0339(17) 0.0111(18) 0.0103(17) 0.000(2) C20 0.070(2) 0.107(3) 0.049(2) 0.009(2) -0.0078(16) 0.011(2) C21 0.0595(19) 0.066(2) 0.063(2) 0.0023(17) 0.0131(17) 0.0257(18) C22 0.057(2) 0.106(3) 0.054(2) 0.007(2) -0.0011(19) 0.005(2) C23 0.099(3) 0.076(3) 0.038(2) 0.0097(17) -0.004(2) -0.028(3) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag C1 C9 1.391(3) . ? C1 C6 1.409(3) . ? C1 C11 1.532(3) . ? O2 C6 1.383(3) . ? O2 C16 1.432(3) . ? N C19 1.355(3) . ? N C21 1.439(3) . ? N C11 1.472(3) . ? C4 C12 1.361(4) . ? C4 O5 1.374(3) . ? C4 C9 1.405(3) . ? O5 C20 1.417(3) . ? C6 C8 1.374(3) . ? O7 C11 1.410(3) . ? C8 C12 1.379(4) . ? C9 C14 1.510(3) . ? C10 C15 1.386(4) . ? C10 C17 1.391(3) . ? C10 C11 1.535(3) . ? O13 C19 1.237(3) . ? C14 C21 1.510(3) . ? C15 C23 1.383(4) . ? C15 C19 1.479(4) . ? C17 C22 1.387(4) . ? C18 C22 1.370(4) . ? C18 C23 1.376(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 C1 C6 118.3(2) . . ? C9 C1 C11 121.7(3) . . ? C6 C1 C11 120.0(2) . . ? C6 O2 C16 118.5(2) . . ? C19 N C21 125.8(2) . . ? C19 N C11 114.1(2) . . ? C21 N C11 118.1(2) . . ? C12 C4 O5 125.0(3) . . ? C12 C4 C9 120.8(3) . . ? O5 C4 C9 114.2(3) . . ? C4 O5 C20 118.3(2) . . ? C8 C6 O2 123.1(3) . . ? C8 C6 C1 121.0(3) . . ? O2 C6 C1 115.8(2) . . ? C6 C8 C12 119.9(3) . . ? C1 C9 C4 119.5(2) . . ? C1 C9 C14 122.6(2) . . ? C4 C9 C14 117.9(2) . . ? C15 C10 C17 119.3(3) . . ? C15 C10 C11 109.8(3) . . ? C17 C10 C11 130.8(3) . . ? O7 C11 N 106.79(18) . . ? O7 C11 C1 111.2(2) . . ? N C11 C1 107.9(2) . . ? O7 C11 C10 112.4(2) . . ? N C11 C10 100.6(2) . . ? C1 C11 C10 116.9(2) . . ? C4 C12 C8 120.4(3) . . ? C21 C14 C9 111.4(2) . . ? C23 C15 C10 122.6(3) . . ? C23 C15 C19 128.9(3) . . ? C10 C15 C19 108.4(3) . . ? C22 C17 C10 118.1(3) . . ? C22 C18 C23 121.4(4) . . ? O13 C19 N 125.4(3) . . ? O13 C19 C15 127.6(3) . . ? N C19 C15 107.0(3) . . ? N C21 C14 108.3(2) . . ? C18 C22 C17 121.4(4) . . ? C18 C23 C15 117.1(3) . . ? _diffrn_measured_fraction_theta_max 0.999 _diffrn_reflns_theta_full 25.00 _diffrn_measured_fraction_theta_full 0.999 _refine_diff_density_max 0.091 _refine_diff_density_min -0.099 _refine_diff_density_rms 0.025 # Attachment 'crr-66-crr-226.cif' data_crr-66-crr-226 _database_code_depnum_ccdc_archive 'CCDC 828128' #TrackingRef 'crr-66-crr-226.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C20 H21 N O6' _chemical_formula_weight 371.38 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 ? _symmetry_space_group_name_H-M ? 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 10.1550(2) _cell_length_b 19.4043(5) _cell_length_c 9.8299(3) _cell_angle_alpha 90.00 _cell_angle_beta 95.344(2) _cell_angle_gamma 90.00 _cell_volume 1928.57(9) _cell_formula_units_Z 4 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description ? _exptl_crystal_colour ? _exptl_crystal_size_max ? _exptl_crystal_size_mid ? _exptl_crystal_size_min ? _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.279 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 784 _exptl_absorpt_coefficient_mu 0.095 _exptl_absorpt_correction_type ? _exptl_absorpt_correction_T_min ? _exptl_absorpt_correction_T_max ? _exptl_absorpt_process_details ? _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 ? _diffrn_measurement_method ? _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 15615 _diffrn_reflns_av_R_equivalents 0.0406 _diffrn_reflns_av_sigmaI/netI 0.0292 _diffrn_reflns_limit_h_min -12 _diffrn_reflns_limit_h_max 12 _diffrn_reflns_limit_k_min -23 _diffrn_reflns_limit_k_max 23 _diffrn_reflns_limit_l_min -11 _diffrn_reflns_limit_l_max 11 _diffrn_reflns_theta_min 2.91 _diffrn_reflns_theta_max 25.00 _reflns_number_total 3380 _reflns_number_gt 2591 _reflns_threshold_expression >2sigma(I) _computing_data_collection ? _computing_cell_refinement ? _computing_data_reduction ? _computing_structure_solution ? _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics ? _computing_publication_material ? _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^)+(0.0517P)^2^+0.5041P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment mixed _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 3380 _refine_ls_number_parameters 267 _refine_ls_number_restraints 3 _refine_ls_R_factor_all 0.0597 _refine_ls_R_factor_gt 0.0419 _refine_ls_wR_factor_ref 0.1099 _refine_ls_wR_factor_gt 0.0999 _refine_ls_goodness_of_fit_ref 1.005 _refine_ls_restrained_S_all 1.005 _refine_ls_shift/su_max 0.029 _refine_ls_shift/su_mean 0.003 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group O1 O 0.28195(12) 0.25754(6) 0.34569(13) 0.0417(3) Uani 1 1 d . . . O2 O 0.16431(13) 0.38426(7) 0.50654(14) 0.0425(3) Uani 1 1 d . . . O3 O -0.24201(13) 0.41165(8) 0.00591(15) 0.0580(4) Uani 1 1 d . . . O4 O 0.43355(13) 0.55318(6) 0.36843(14) 0.0479(4) Uani 1 1 d . . . O5 O -0.11807(14) 0.29724(7) 0.06346(17) 0.0620(4) Uani 1 1 d . . . N N 0.26085(14) 0.48427(7) 0.41690(16) 0.0394(4) Uani 1 1 d . . . O7 O 0.52037(12) 0.22616(7) 0.27745(16) 0.0536(4) Uani 1 1 d . . . C9 C 0.49693(17) 0.29481(9) 0.29428(19) 0.0390(4) Uani 1 1 d . . . C10 C 0.36932(16) 0.31061(9) 0.33093(17) 0.0333(4) Uani 1 1 d . . . C11 C 0.02973(17) 0.47833(9) 0.24733(19) 0.0385(4) Uani 1 1 d . . . C12 C 0.04599(17) 0.35516(9) 0.22004(19) 0.0400(4) Uani 1 1 d . . . H12 H 0.0895 0.3140 0.2426 0.048 Uiso 1 1 calc R . . C13 C 0.33740(16) 0.37908(9) 0.34679(16) 0.0319(4) Uani 1 1 d . . . C C 0.21153(17) 0.41349(9) 0.38963(18) 0.0349(4) Uani 1 1 d . . . C15 C 0.09417(16) 0.41652(9) 0.28059(18) 0.0348(4) Uani 1 1 d . . . C16 C -0.08373(18) 0.47697(10) 0.15512(19) 0.0437(5) Uani 1 1 d . . . H16 H -0.1282 0.5180 0.1334 0.052 Uiso 1 1 calc R . . C17 C -0.06445(17) 0.35454(10) 0.1278(2) 0.0434(5) Uani 1 1 d . . . C18 C -0.13123(18) 0.41695(10) 0.0958(2) 0.0427(5) Uani 1 1 d . . . C19 C 0.43272(16) 0.42940(9) 0.33280(17) 0.0345(4) Uani 1 1 d . . . C20 C 0.58890(18) 0.34603(10) 0.2767(2) 0.0453(5) Uani 1 1 d . . . H20 H 0.6719 0.3345 0.2508 0.054 Uiso 1 1 calc R . . C21 C 0.55738(18) 0.41404(10) 0.29762(19) 0.0412(5) Uani 1 1 d . . . H21 H 0.6190 0.4488 0.2882 0.049 Uiso 1 1 calc R . . C22 C 0.38077(18) 0.49626(9) 0.37236(18) 0.0365(4) Uani 1 1 d . . . C23 C 0.0764(2) 0.54695(10) 0.3062(2) 0.0472(5) Uani 1 1 d . . . H23A H 0.0002 0.5745 0.3246 0.057 Uiso 1 1 calc R . . H23B H 0.1234 0.5714 0.2396 0.057 Uiso 1 1 calc R . . C25 C -0.0494(2) 0.23435(12) 0.0828(3) 0.0809(8) Uani 1 1 d . . . H25A H -0.0939 0.1994 0.0267 0.121 Uiso 1 1 calc R . . H25B H -0.0466 0.2210 0.1771 0.121 Uiso 1 1 calc R . . H25C H 0.0392 0.2398 0.0578 0.121 Uiso 1 1 calc R . . C26 C 0.16597(19) 0.53854(10) 0.4365(2) 0.0459(5) Uani 1 1 d . . . H26A H 0.2120 0.5814 0.4591 0.055 Uiso 1 1 calc R . . H26B H 0.1142 0.5266 0.5112 0.055 Uiso 1 1 calc R . . C27 C -0.3149(2) 0.47320(13) -0.0256(2) 0.0664(7) Uani 1 1 d . . . H27A H -0.3918 0.4627 -0.0865 0.100 Uiso 1 1 calc R . . H27B H -0.2603 0.5055 -0.0685 0.100 Uiso 1 1 calc R . . H27C H -0.3418 0.4929 0.0571 0.100 Uiso 1 1 calc R . . C0AA C 0.3034(2) 0.22288(11) 0.4754(2) 0.0578(6) Uani 1 1 d . . . H0AA H 0.2421 0.1853 0.4780 0.087 Uiso 1 1 calc R . . H0AB H 0.2901 0.2548 0.5476 0.087 Uiso 1 1 calc R . . H0AC H 0.3922 0.2055 0.4871 0.087 Uiso 1 1 calc R . . C1AA C 0.6502(2) 0.20633(13) 0.2469(3) 0.0829(9) Uani 1 1 d . . . H1AA H 0.6708 0.2286 0.1643 0.124 Uiso 1 1 calc R . . H1AB H 0.6534 0.1573 0.2351 0.124 Uiso 1 1 calc R . . H1AC H 0.7136 0.2198 0.3207 0.124 Uiso 1 1 calc R . . O O 0.34351(15) 0.39397(8) 0.72655(17) 0.0586(4) Uani 1 1 d D . . H2 H 0.230(2) 0.3883(12) 0.576(3) 0.074(8) Uiso 1 1 d . . . HA H 0.367(3) 0.3535(7) 0.751(3) 0.111 Uiso 1 1 d D . . HB H 0.4110(19) 0.4137(13) 0.697(3) 0.111 Uiso 1 1 d D . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 O1 0.0409(7) 0.0321(7) 0.0523(8) 0.0038(6) 0.0048(6) -0.0032(6) O2 0.0430(7) 0.0454(8) 0.0405(8) 0.0032(6) 0.0125(6) -0.0019(6) O3 0.0473(8) 0.0650(10) 0.0595(9) 0.0031(7) -0.0066(7) 0.0120(7) O4 0.0542(8) 0.0331(8) 0.0568(9) 0.0010(6) 0.0071(6) -0.0088(6) O5 0.0481(8) 0.0442(8) 0.0902(12) -0.0112(7) -0.0125(8) 0.0001(7) N 0.0405(8) 0.0305(8) 0.0481(9) -0.0046(7) 0.0098(7) -0.0001(7) O7 0.0411(7) 0.0378(8) 0.0833(11) -0.0101(7) 0.0137(7) 0.0066(6) C9 0.0383(10) 0.0350(10) 0.0436(11) -0.0031(8) 0.0041(8) 0.0052(8) C10 0.0340(9) 0.0334(10) 0.0326(9) 0.0012(7) 0.0026(7) -0.0028(8) C11 0.0394(10) 0.0351(10) 0.0426(11) 0.0029(8) 0.0126(8) 0.0065(8) C12 0.0333(9) 0.0318(10) 0.0551(12) 0.0023(8) 0.0060(8) 0.0043(8) C13 0.0337(9) 0.0321(9) 0.0302(9) 0.0015(7) 0.0038(7) 0.0008(7) C 0.0372(9) 0.0296(10) 0.0393(10) 0.0004(7) 0.0102(8) 0.0009(7) C15 0.0327(9) 0.0320(10) 0.0410(10) 0.0031(8) 0.0111(8) 0.0024(8) C16 0.0444(11) 0.0401(11) 0.0477(12) 0.0083(9) 0.0103(9) 0.0130(9) C17 0.0353(10) 0.0401(11) 0.0551(12) -0.0023(9) 0.0064(9) -0.0007(8) C18 0.0359(10) 0.0484(12) 0.0442(11) 0.0041(9) 0.0053(8) 0.0056(9) C19 0.0368(9) 0.0344(10) 0.0321(10) 0.0018(7) 0.0031(7) -0.0017(8) C20 0.0343(10) 0.0461(12) 0.0573(12) -0.0031(9) 0.0132(9) 0.0026(9) C21 0.0367(10) 0.0411(11) 0.0472(11) 0.0006(8) 0.0107(8) -0.0058(8) C22 0.0405(10) 0.0347(10) 0.0340(10) 0.0020(7) 0.0015(8) -0.0026(8) C23 0.0498(11) 0.0323(11) 0.0615(13) -0.0005(9) 0.0157(10) 0.0090(9) C25 0.0554(14) 0.0436(14) 0.140(3) -0.0231(14) -0.0093(15) 0.0010(11) C26 0.0519(12) 0.0333(10) 0.0542(12) -0.0083(8) 0.0146(10) 0.0020(9) C27 0.0596(14) 0.0855(18) 0.0525(14) 0.0090(12) -0.0041(11) 0.0299(13) C0AA 0.0766(15) 0.0436(12) 0.0561(14) 0.0120(10) 0.0217(11) 0.0024(11) C1AA 0.0494(13) 0.0511(15) 0.151(3) -0.0206(15) 0.0235(15) 0.0125(11) O 0.0575(9) 0.0560(10) 0.0628(10) 0.0136(8) 0.0081(8) 0.0004(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 O1 C10 1.376(2) . ? O1 C0AA 1.440(2) . ? O2 C 1.405(2) . ? O3 C18 1.368(2) . ? O3 C27 1.424(2) . ? O4 C22 1.230(2) . ? O5 C17 1.367(2) . ? O5 C25 1.410(3) . ? N C22 1.352(2) . ? N C26 1.452(2) . ? N C 1.478(2) . ? O7 C9 1.366(2) . ? O7 C1AA 1.432(2) . ? C9 C20 1.386(3) . ? C9 C10 1.411(2) . ? C10 C13 1.380(2) . ? C11 C15 1.391(2) . ? C11 C16 1.398(3) . ? C11 C23 1.510(3) . ? C12 C17 1.375(2) . ? C12 C15 1.399(2) . ? C13 C19 1.391(2) . ? C13 C 1.535(2) . ? C C15 1.528(2) . ? C16 C18 1.370(3) . ? C17 C18 1.409(3) . ? C19 C21 1.376(2) . ? C19 C22 1.466(2) . ? C20 C21 1.378(3) . ? C23 C26 1.509(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 C10 O1 C0AA 113.40(14) . . ? C18 O3 C27 117.18(17) . . ? C17 O5 C25 118.09(16) . . ? C22 N C26 123.15(15) . . ? C22 N C 113.66(14) . . ? C26 N C 118.70(14) . . ? C9 O7 C1AA 117.50(16) . . ? O7 C9 C20 123.87(16) . . ? O7 C9 C10 114.68(15) . . ? C20 C9 C10 121.45(16) . . ? O1 C10 C13 123.25(15) . . ? O1 C10 C9 118.75(15) . . ? C13 C10 C9 117.98(16) . . ? C15 C11 C16 118.52(17) . . ? C15 C11 C23 123.12(16) . . ? C16 C11 C23 118.36(16) . . ? C17 C12 C15 121.30(16) . . ? C10 C13 C19 119.47(15) . . ? C10 C13 C 131.30(15) . . ? C19 C13 C 109.07(14) . . ? O2 C N 111.25(14) . . ? O2 C C15 106.61(14) . . ? N C C15 108.69(13) . . ? O2 C C13 113.89(14) . . ? N C C13 100.20(13) . . ? C15 C C13 116.06(14) . . ? C11 C15 C12 119.72(16) . . ? C11 C15 C 121.16(15) . . ? C12 C15 C 118.99(15) . . ? C18 C16 C11 121.88(17) . . ? O5 C17 C12 125.28(17) . . ? O5 C17 C18 115.67(16) . . ? C12 C17 C18 119.04(17) . . ? O3 C18 C16 125.07(17) . . ? O3 C18 C17 115.40(17) . . ? C16 C18 C17 119.53(17) . . ? C21 C19 C13 122.54(16) . . ? C21 C19 C22 128.36(16) . . ? C13 C19 C22 108.90(15) . . ? C21 C20 C9 119.99(17) . . ? C19 C21 C20 118.49(17) . . ? O4 C22 N 124.96(17) . . ? O4 C22 C19 128.14(17) . . ? N C22 C19 106.90(15) . . ? C11 C23 C26 111.87(15) . . ? N C26 C23 108.72(15) . . ? _diffrn_measured_fraction_theta_max 0.999 _diffrn_reflns_theta_full 25.00 _diffrn_measured_fraction_theta_full 0.999 _refine_diff_density_max 0.148 _refine_diff_density_min -0.207 _refine_diff_density_rms 0.036