# Electronic Supplementary Material (ESI) for RSC Advances # This journal is © The Royal Society of Chemistry 2012 ####################################################################### # # Cambridge Crystallographic Data Centre # CCDC # ####################################################################### # # This CIF contains data from an original supplementary publication # deposited with the CCDC, and may include chemical, crystal, # experimental, refinement, atomic coordinates, # anisotropic displacement parameters and molecular geometry data, # as required by the journal to which it was submitted. # # This CIF is provided on the understanding that it is used for bona # fide research purposes only. It may contain copyright material # of the CCDC or of third parties, and may not be copied or further # disseminated in any form, whether machine-readable or not, # except for the purpose of generating routine backup copies # on your local computer system. # # For further information on the CCDC, data deposition and # data retrieval see: # www.ccdc.cam.ac.uk # # Bona fide researchers may freely download Mercury and enCIFer # from this site to visualise CIF-encoded structures and # to carry out CIF format checking respectively. # ####################################################################### data_crr-72 _database_code_depnum_ccdc_archive 'CCDC 876034' #TrackingRef 'CRR-72.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; 12-fluoro-7,8,13,13b-tetrahydro-5H-benzo[1,2]indolizino[8,7-b]indol-5-one ; _chemical_name_common ; 12-fluoro-7,8,13,13b-tetrahydro-5H-benzo[1,2]indolizino[8,7-b]indol-5-one ; _chemical_melting_point 503 _chemical_formula_moiety 'C18 H13 F N2 O' _chemical_formula_sum 'C18 H13 F N2 O' _chemical_formula_weight 292.30 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' F F 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting ? _symmetry_space_group_name_H-M P121/n1 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, y+1/2, -z+1/2' '-x, -y, -z' 'x-1/2, -y-1/2, z-1/2' _cell_length_a 4.6857(5) _cell_length_b 13.4725(18) _cell_length_c 22.520(2) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 1421.6(3) _cell_formula_units_Z 4 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used 2345 _cell_measurement_theta_min 2.7079 _cell_measurement_theta_max 29.3696 _exptl_crystal_description ? _exptl_crystal_colour colorless _exptl_crystal_size_max 0.6 _exptl_crystal_size_mid 0.4 _exptl_crystal_size_min 0.06 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.366 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 537 _exptl_absorpt_coefficient_mu 0.095 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.74377 _exptl_absorpt_correction_T_max 1.00000 _exptl_absorpt_process_details ; CrysAlisPro, Oxford Diffraction Ltd., Version 1.171.34.44 (release 25-10-2010 CrysAlis171 .NET) (compiled Oct 25 2010,18:11:34) Empirical absorption correction using spherical harmonics, implemented in SCALE3 ABSPACK scaling algorithm. ; _exptl_special_details ; ? ; _diffrn_ambient_temperature 293(2) _diffrn_radiation_wavelength 0.7107 _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 _diffrn_detector_area_resol_mean 15.9821 _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 5764 _diffrn_reflns_av_R_equivalents 0.0234 _diffrn_reflns_av_sigmaI/netI 0.0361 _diffrn_reflns_limit_h_min -5 _diffrn_reflns_limit_h_max 5 _diffrn_reflns_limit_k_min -16 _diffrn_reflns_limit_k_max 15 _diffrn_reflns_limit_l_min -26 _diffrn_reflns_limit_l_max 16 _diffrn_reflns_theta_min 3.02 _diffrn_reflns_theta_max 25.00 _reflns_number_total 2375 _reflns_number_gt 1781 _reflns_threshold_expression >2sigma(I) _computing_data_collection ; CrysAlisPro, Oxford Diffraction Ltd., Version 1.171.34.44 (release 25-10-2010 CrysAlis171 .NET) (compiled Oct 25 2010,18:11:34) ; _computing_cell_refinement ; CrysAlisPro, Oxford Diffraction Ltd., Version 1.171.34.44 (release 25-10-2010 CrysAlis171 .NET) (compiled Oct 25 2010,18:11:34) ; _computing_data_reduction ; CrysAlisPro, Oxford Diffraction Ltd., Version 1.171.34.44 (release 25-10-2010 CrysAlis171 .NET) (compiled Oct 25 2010,18:11:34) ; _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^)+(0.0441P)^2^+0.1734P] 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 2375 _refine_ls_number_parameters 199 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0658 _refine_ls_R_factor_gt 0.0447 _refine_ls_wR_factor_ref 0.1073 _refine_ls_wR_factor_gt 0.0951 _refine_ls_goodness_of_fit_ref 1.049 _refine_ls_restrained_S_all 1.049 _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 N N 0.2261(3) 0.26130(11) 0.15658(7) 0.0436(4) Uani 1 1 d . . . H H 0.1799 0.3099 0.1794 0.052 Uiso 1 1 calc R . . N0AA N 0.6304(3) 0.06275(12) 0.23170(7) 0.0424(4) Uani 1 1 d . . . C3 C 0.5268(4) 0.16529(14) 0.23131(8) 0.0406(5) Uani 1 1 d . . . H3 H 0.6846 0.2116 0.2383 0.049 Uiso 1 1 calc R . . C4 C 0.4292(4) 0.12018(14) 0.12410(8) 0.0394(5) Uani 1 1 d . . . C5 C 0.2624(4) 0.16020(15) 0.07699(8) 0.0423(5) Uani 1 1 d . . . C6 C 0.3986(4) 0.18264(13) 0.17143(8) 0.0370(4) Uani 1 1 d . . . C7 C 0.4924(4) 0.00412(16) 0.27143(8) 0.0431(5) Uani 1 1 d . . . C8 C 0.3240(4) 0.16476(15) 0.28402(8) 0.0407(5) Uani 1 1 d . . . O9 O 0.5257(3) -0.08636(11) 0.27519(6) 0.0632(4) Uani 1 1 d . . . C10 C 0.5979(4) 0.02617(15) 0.12583(9) 0.0518(5) Uani 1 1 d . . . H10A H 0.7160 0.0214 0.0906 0.062 Uiso 1 1 calc R . . H10B H 0.4694 -0.0303 0.1263 0.062 Uiso 1 1 calc R . . C11 C 0.1407(4) 0.24823(15) 0.09876(8) 0.0432(5) Uani 1 1 d . . . C12 C 0.3049(4) 0.06969(15) 0.30626(8) 0.0423(5) Uani 1 1 d . . . F F -0.1537(3) 0.38815(11) 0.08500(6) 0.0924(5) Uani 1 1 d . . . C14 C 0.7845(4) 0.02424(16) 0.18060(9) 0.0512(5) Uani 1 1 d . . . H14A H 0.8447 -0.0434 0.1885 0.061 Uiso 1 1 calc R . . H14B H 0.9538 0.0641 0.1738 0.061 Uiso 1 1 calc R . . C15 C 0.1752(5) 0.24164(17) 0.31036(9) 0.0539(6) Uani 1 1 d . . . H15 H 0.1919 0.3064 0.2965 0.065 Uiso 1 1 calc R . . C16 C 0.1289(4) 0.04706(18) 0.35408(9) 0.0547(6) Uani 1 1 d . . . H16 H 0.1153 -0.0175 0.3685 0.066 Uiso 1 1 calc R . . C17 C -0.0366(5) 0.30316(17) 0.06307(10) 0.0599(6) Uani 1 1 d . . . C18 C -0.0248(5) 0.1233(2) 0.37951(10) 0.0645(7) Uani 1 1 d . . . H18 H -0.1459 0.1101 0.4113 0.077 Uiso 1 1 calc R . . C19 C 0.1997(5) 0.12872(18) 0.01932(9) 0.0578(6) Uani 1 1 d . . . H19 H 0.2786 0.0706 0.0043 0.069 Uiso 1 1 calc R . . C20 C 0.0206(5) 0.1850(2) -0.01449(10) 0.0700(7) Uani 1 1 d . . . H20 H -0.0235 0.1642 -0.0528 0.084 Uiso 1 1 calc R . . C21 C -0.0980(5) 0.2728(2) 0.00691(11) 0.0713(7) Uani 1 1 d . . . H21 H -0.2183 0.3104 -0.0170 0.086 Uiso 1 1 calc R . . C22 C -0.0002(5) 0.2188(2) 0.35820(10) 0.0655(7) Uani 1 1 d . . . H22 H -0.1038 0.2694 0.3763 0.079 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 N 0.0597(9) 0.0406(10) 0.0304(9) -0.0045(8) -0.0026(8) 0.0001(8) N0AA 0.0417(8) 0.0479(11) 0.0376(9) 0.0052(8) 0.0017(7) -0.0035(7) C3 0.0451(10) 0.0418(12) 0.0348(11) 0.0010(9) -0.0024(9) -0.0101(8) C4 0.0436(10) 0.0424(12) 0.0323(11) -0.0021(9) 0.0034(9) -0.0063(8) C5 0.0482(10) 0.0506(13) 0.0281(11) -0.0027(10) 0.0065(9) -0.0106(9) C6 0.0418(9) 0.0378(11) 0.0312(10) 0.0020(9) 0.0016(8) -0.0080(8) C7 0.0467(10) 0.0470(14) 0.0355(12) 0.0034(10) -0.0058(9) -0.0094(9) C8 0.0432(10) 0.0543(13) 0.0246(10) -0.0034(10) -0.0097(8) -0.0061(9) O9 0.0872(11) 0.0453(10) 0.0571(10) 0.0075(8) 0.0088(8) -0.0063(8) C10 0.0584(12) 0.0512(14) 0.0460(13) -0.0080(11) 0.0097(11) -0.0001(10) C11 0.0508(10) 0.0492(13) 0.0296(11) 0.0025(10) 0.0004(9) -0.0045(9) C12 0.0427(9) 0.0555(14) 0.0288(10) -0.0010(10) -0.0063(9) -0.0112(9) F 0.1143(12) 0.0893(11) 0.0735(10) 0.0001(9) -0.0167(9) 0.0414(9) C14 0.0449(10) 0.0559(14) 0.0528(13) 0.0030(11) 0.0089(10) 0.0017(9) C15 0.0677(12) 0.0609(15) 0.0329(11) -0.0084(11) -0.0087(11) 0.0028(11) C16 0.0556(11) 0.0724(16) 0.0363(12) 0.0024(11) -0.0005(10) -0.0139(11) C17 0.0671(13) 0.0659(16) 0.0468(14) 0.0042(12) -0.0017(12) 0.0081(12) C18 0.0561(13) 0.102(2) 0.0349(13) -0.0029(14) 0.0053(11) -0.0077(13) C19 0.0643(13) 0.0764(17) 0.0328(12) -0.0096(12) 0.0049(11) -0.0065(12) C20 0.0748(15) 0.106(2) 0.0297(12) -0.0058(14) -0.0046(12) -0.0083(15) C21 0.0699(14) 0.105(2) 0.0393(14) 0.0134(14) -0.0128(12) 0.0039(14) C22 0.0683(14) 0.093(2) 0.0348(13) -0.0133(13) -0.0038(11) 0.0144(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 N C11 1.373(2) . ? N C6 1.374(2) . ? N0AA C7 1.357(2) . ? N0AA C14 1.454(2) . ? N0AA C3 1.464(2) . ? C3 C6 1.495(2) . ? C3 C8 1.520(2) . ? C4 C6 1.366(2) . ? C4 C5 1.424(3) . ? C4 C10 1.493(3) . ? C5 C19 1.397(3) . ? C5 C11 1.404(3) . ? C7 O9 1.232(2) . ? C7 C12 1.472(3) . ? C8 C12 1.378(3) . ? C8 C15 1.382(3) . ? C10 C14 1.512(3) . ? C11 C17 1.373(3) . ? C12 C16 1.390(3) . ? F C17 1.362(2) . ? C15 C22 1.389(3) . ? C16 C18 1.379(3) . ? C17 C21 1.360(3) . ? C18 C22 1.379(3) . ? C19 C20 1.363(3) . ? C20 C21 1.393(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 C11 N C6 107.64(16) . . ? C7 N0AA C14 123.41(17) . . ? C7 N0AA C3 113.25(16) . . ? C14 N0AA C3 119.77(15) . . ? N0AA C3 C6 106.63(15) . . ? N0AA C3 C8 101.43(15) . . ? C6 C3 C8 117.00(15) . . ? C6 C4 C5 106.88(17) . . ? C6 C4 C10 123.92(17) . . ? C5 C4 C10 129.13(17) . . ? C19 C5 C11 119.71(19) . . ? C19 C5 C4 133.9(2) . . ? C11 C5 C4 106.41(16) . . ? C4 C6 N 110.32(16) . . ? C4 C6 C3 124.44(17) . . ? N C6 C3 125.20(16) . . ? O9 C7 N0AA 124.11(19) . . ? O9 C7 C12 129.25(18) . . ? N0AA C7 C12 106.64(18) . . ? C12 C8 C15 120.51(19) . . ? C12 C8 C3 109.19(17) . . ? C15 C8 C3 130.29(19) . . ? C4 C10 C14 109.99(17) . . ? C17 C11 N 131.5(2) . . ? C17 C11 C5 119.77(18) . . ? N C11 C5 108.73(16) . . ? C8 C12 C16 121.59(19) . . ? C8 C12 C7 108.98(17) . . ? C16 C12 C7 129.4(2) . . ? N0AA C14 C10 110.63(15) . . ? C8 C15 C22 117.7(2) . . ? C18 C16 C12 117.9(2) . . ? C21 C17 F 120.3(2) . . ? C21 C17 C11 120.7(2) . . ? F C17 C11 119.0(2) . . ? C16 C18 C22 120.5(2) . . ? C20 C19 C5 118.7(2) . . ? C19 C20 C21 121.6(2) . . ? C17 C21 C20 119.5(2) . . ? C18 C22 C15 121.7(2) . . ? _diffrn_measured_fraction_theta_max 0.999 _diffrn_reflns_theta_full 25.00 _diffrn_measured_fraction_theta_full 0.999 _refine_diff_density_max 0.156 _refine_diff_density_min -0.164 _refine_diff_density_rms 0.032 data_crr-crr-304 _database_code_depnum_ccdc_archive 'CCDC 876035' _audit_creation_date 2011-10-31 _audit_creation_method ; Olex2 1.1 (compiled 2011.02.15 svn.r1672, GUI svn.r3494) ; _chemical_name_common 10,12-dimethyl-7,8,13,13b-tetrahydro-5H-benzo[1,2]indolizino[8,7-b]indol-5-one _chemical_name_systematic ; 10,12-dimethyl-7,8,13,13b-tetrahydro-5H-benzo[1,2]indolizino[8,7-b]indol-5-one ; _chemical_formula_moiety 'C20 H18 N2 O' _chemical_formula_sum 'C20 H18 N2 O' _chemical_formula_weight 302.36 _chemical_melting_point 473 _chemical_oxdiff_formula 'C20 H18 N2 O1' _chemical_oxdiff_usercomment '300 K, COLORLESS, PLATE, .45 .25 .08' 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 monoclinic _space_group_IT_number 14 _space_group_name_H-M_alt 'P 1 21/n 1' _space_group_name_Hall '-P 2yn' loop_ _space_group_symop_id _space_group_symop_operation_xyz 1 'x, y, z' 2 '-x+1/2, y+1/2, -z+1/2' 3 '-x, -y, -z' 4 'x-1/2, -y-1/2, z-1/2' _cell_length_a 5.1005(3) _cell_length_b 12.8705(7) _cell_length_c 23.9984(14) _cell_angle_alpha 90.00 _cell_angle_beta 90.250(5) _cell_angle_gamma 90.00 _cell_volume 1575.37(16) _cell_formula_units_Z 4 _cell_measurement_reflns_used 3474 _cell_measurement_temperature 293(2) _cell_measurement_theta_max 29.1530 _cell_measurement_theta_min 2.9922 _exptl_absorpt_coefficient_mu 0.079 _exptl_absorpt_correction_T_max 1.00000 _exptl_absorpt_correction_T_min 0.72709 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details ; CrysAlisPro, Oxford Diffraction Ltd., Version 1.171.34.44 (release 25-10-2010 CrysAlis171 .NET) (compiled Oct 25 2010,18:11:34) Empirical absorption correction using spherical harmonics, implemented in SCALE3 ABSPACK scaling algorithm. ; _exptl_crystal_colour colorless _exptl_crystal_density_diffrn 1.275 _exptl_crystal_density_meas ? _exptl_crystal_density_method 'not measured' _exptl_crystal_description ? _exptl_crystal_F_000 640 _exptl_crystal_size_max 0.45 _exptl_crystal_size_mid 0.25 _exptl_crystal_size_min 0.08 _exptl_special_details ; ? ; _diffrn_reflns_av_R_equivalents 0.0307 _diffrn_reflns_av_unetI/netI 0.0446 _diffrn_reflns_limit_h_max 5 _diffrn_reflns_limit_h_min -6 _diffrn_reflns_limit_k_max 15 _diffrn_reflns_limit_k_min -14 _diffrn_reflns_limit_l_max 28 _diffrn_reflns_limit_l_min -28 _diffrn_reflns_number 7159 _diffrn_reflns_theta_full 25.00 _diffrn_reflns_theta_max 25.00 _diffrn_reflns_theta_min 3.00 _diffrn_ambient_temperature 293(2) _diffrn_detector_area_resol_mean 15.9821 _diffrn_measured_fraction_theta_full 0.996 _diffrn_measured_fraction_theta_max 0.996 _diffrn_measurement_details ; #__ type_ start__ end____ width___ exp.time_ 1 omega -43.00 33.00 1.0000 51.4000 omega____ theta____ kappa____ phi______ frames - -17.4960 37.0000 60.0000 76 #__ type_ start__ end____ width___ exp.time_ 2 omega -42.00 47.00 1.0000 51.4000 omega____ theta____ kappa____ phi______ frames - -17.4960 37.0000 150.0000 89 #__ type_ start__ end____ width___ exp.time_ 3 omega 28.00 71.00 1.0000 51.4000 omega____ theta____ kappa____ phi______ frames - 19.1366 -116.0000 -120.0000 43 #__ type_ start__ end____ width___ exp.time_ 4 omega -88.00 -27.00 1.0000 51.4000 omega____ theta____ kappa____ phi______ frames - -17.4960 -77.0000 30.0000 61 ; _diffrn_measurement_device_type 'Xcalibur, Eos' _diffrn_measurement_method '\w scans' _diffrn_orient_matrix_UB_11 -0.1341660000 _diffrn_orient_matrix_UB_12 -0.0011458000 _diffrn_orient_matrix_UB_13 0.0076541000 _diffrn_orient_matrix_UB_21 0.0365868000 _diffrn_orient_matrix_UB_22 -0.0087161000 _diffrn_orient_matrix_UB_23 0.0281721000 _diffrn_orient_matrix_UB_31 0.0031654000 _diffrn_orient_matrix_UB_32 0.0543738000 _diffrn_orient_matrix_UB_33 0.0046979000 _diffrn_radiation_monochromator graphite _diffrn_radiation_type 'Mo K\a' _diffrn_radiation_wavelength 0.7107 _diffrn_source 'Enhance (Mo) X-ray Source' _diffrn_standards_decay_% ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_number ? _reflns_number_gt 1952 _reflns_number_total 2763 _reflns_odcompleteness_completeness 99.47 _reflns_odcompleteness_iscentric 1 _reflns_odcompleteness_theta 26.32 _reflns_threshold_expression >2sigma(I) _computing_cell_refinement ; CrysAlisPro, Oxford Diffraction Ltd., Version 1.171.34.44 (release 25-10-2010 CrysAlis171 .NET) (compiled Oct 25 2010,18:11:34) ; _computing_data_collection ; CrysAlisPro, Oxford Diffraction Ltd., Version 1.171.34.44 (release 25-10-2010 CrysAlis171 .NET) (compiled Oct 25 2010,18:11:34) ; _computing_data_reduction ; CrysAlisPro, Oxford Diffraction Ltd., Version 1.171.34.44 (release 25-10-2010 CrysAlis171 .NET) (compiled Oct 25 2010,18:11:34) ; _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 0.212 _refine_diff_density_min -0.165 _refine_diff_density_rms 0.034 _refine_ls_extinction_coef ? _refine_ls_extinction_method none _refine_ls_goodness_of_fit_ref 1.038 _refine_ls_hydrogen_treatment constr _refine_ls_matrix_type full _refine_ls_number_parameters 210 _refine_ls_number_reflns 2763 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0708 _refine_ls_R_factor_gt 0.0443 _refine_ls_restrained_S_all 1.038 _refine_ls_shift/su_max 0.001 _refine_ls_shift/su_mean 0.000 _refine_ls_structure_factor_coef Fsqd _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0517P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_gt 0.1006 _refine_ls_wR_factor_ref 0.1107 _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 N1 N 0.1848(3) 0.67976(9) 0.15244(6) 0.0373(4) Uani 1 1 d . . . H1 H 0.1284 0.6268 0.1707 0.045 Uiso 1 1 calc R . . O O 0.5805(3) 1.00663(9) 0.28561(5) 0.0503(4) Uani 1 1 d . . . N3 N 0.6165(3) 0.85622(11) 0.23475(6) 0.0399(4) Uani 1 1 d . . . C4 C 0.2525(3) 0.79721(12) 0.08413(7) 0.0359(4) Uani 1 1 d . . . C5 C 0.4822(4) 0.75509(12) 0.22902(7) 0.0383(5) Uani 1 1 d . . . H5 H 0.6071 0.6980 0.2342 0.046 Uiso 1 1 calc R . . C6 C 0.2907(4) 0.75864(13) 0.27675(7) 0.0377(5) Uani 1 1 d . . . C7 C -0.0760(4) 0.66318(12) 0.06295(8) 0.0413(5) Uani 1 1 d . . . C8 C 0.1094(4) 0.70777(12) 0.09877(7) 0.0354(4) Uani 1 1 d . . . C9 C 0.2031(4) 0.84500(13) 0.03266(8) 0.0431(5) Uani 1 1 d . . . H9 H 0.2973 0.9038 0.0224 0.052 Uiso 1 1 calc R . . C10 C 0.4151(4) 0.82259(12) 0.13070(8) 0.0368(4) Uani 1 1 d . . . C11 C 0.3127(4) 0.85388(12) 0.30377(7) 0.0385(5) Uani 1 1 d . . . C12 C 0.7727(4) 0.89597(14) 0.18901(8) 0.0467(5) Uani 1 1 d . . . H12A H 0.9130 0.8475 0.1808 0.056 Uiso 1 1 calc R . . H12B H 0.8512 0.9617 0.1997 0.056 Uiso 1 1 calc R . . C13 C 0.1124(4) 0.68592(14) 0.29514(8) 0.0465(5) Uani 1 1 d . . . H13 H 0.1003 0.6211 0.2782 0.056 Uiso 1 1 calc R . . C14 C 0.0154(4) 0.80499(14) -0.00265(8) 0.0457(5) Uani 1 1 d . . . C15 C 0.6036(4) 0.91127(13) 0.13736(8) 0.0464(5) Uani 1 1 d . . . H15A H 0.5069 0.9759 0.1405 0.056 Uiso 1 1 calc R . . H15B H 0.7146 0.9157 0.1047 0.056 Uiso 1 1 calc R . . C16 C 0.5146(4) 0.91636(14) 0.27556(7) 0.0386(5) Uani 1 1 d . . . C17 C 0.3661(3) 0.75154(12) 0.17154(7) 0.0344(4) Uani 1 1 d . . . C18 C -0.1179(4) 0.71452(14) 0.01320(8) 0.0471(5) Uani 1 1 d . . . H18 H -0.2421 0.6874 -0.0113 0.056 Uiso 1 1 calc R . . C19 C 0.1542(4) 0.87934(14) 0.34826(8) 0.0488(5) Uani 1 1 d . . . H19 H 0.1703 0.9434 0.3659 0.059 Uiso 1 1 calc R . . C20 C -0.0292(4) 0.80737(15) 0.36598(8) 0.0543(6) Uani 1 1 d . . . H20 H -0.1395 0.8230 0.3956 0.065 Uiso 1 1 calc R . . C21 C -0.0479(4) 0.71170(15) 0.33935(8) 0.0518(5) Uani 1 1 d . . . H21 H -0.1714 0.6638 0.3516 0.062 Uiso 1 1 calc R . . C22 C -0.0579(5) 0.85929(15) -0.05640(8) 0.0645(6) Uani 1 1 d . . . H22A H -0.2308 0.8881 -0.0532 0.097 Uiso 1 1 calc R . . H22B H -0.0547 0.8102 -0.0865 0.097 Uiso 1 1 calc R . . H22C H 0.0653 0.9140 -0.0636 0.097 Uiso 1 1 calc R . . C23 C -0.2281(4) 0.56749(14) 0.07826(9) 0.0607(6) Uani 1 1 d . . . H23A H -0.1129 0.5085 0.0785 0.091 Uiso 1 1 calc R . . H23B H -0.3656 0.5565 0.0514 0.091 Uiso 1 1 calc R . . H23C H -0.3031 0.5763 0.1146 0.091 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 N1 0.0455(10) 0.0293(8) 0.0370(9) 0.0018(6) -0.0013(7) -0.0025(7) O 0.0629(10) 0.0327(7) 0.0552(9) -0.0093(6) -0.0065(7) 0.0019(6) N3 0.0383(10) 0.0367(8) 0.0448(10) -0.0067(7) -0.0055(8) 0.0012(7) C4 0.0376(11) 0.0344(10) 0.0358(11) -0.0027(8) 0.0049(9) 0.0009(8) C5 0.0414(11) 0.0302(9) 0.0433(11) -0.0037(8) -0.0072(9) 0.0060(8) C6 0.0433(12) 0.0367(10) 0.0331(10) 0.0011(8) -0.0103(9) 0.0074(9) C7 0.0450(12) 0.0395(10) 0.0393(11) -0.0029(8) -0.0004(9) -0.0035(9) C8 0.0399(11) 0.0336(9) 0.0326(11) -0.0026(8) 0.0005(9) 0.0027(8) C9 0.0484(13) 0.0393(10) 0.0417(12) 0.0026(8) 0.0107(10) -0.0014(9) C10 0.0354(11) 0.0327(10) 0.0423(11) -0.0039(8) 0.0042(9) -0.0006(8) C11 0.0449(12) 0.0346(10) 0.0360(11) -0.0027(8) -0.0109(9) 0.0105(9) C12 0.0366(12) 0.0470(11) 0.0566(13) -0.0084(9) 0.0026(10) -0.0044(9) C13 0.0585(14) 0.0410(11) 0.0400(12) 0.0017(9) -0.0078(10) -0.0012(10) C14 0.0531(13) 0.0504(12) 0.0335(11) 0.0006(9) 0.0023(10) 0.0029(10) C15 0.0451(12) 0.0431(11) 0.0511(13) -0.0046(9) 0.0026(10) -0.0064(9) C16 0.0410(12) 0.0343(10) 0.0404(11) -0.0042(8) -0.0118(9) 0.0103(9) C17 0.0343(11) 0.0300(9) 0.0389(11) -0.0050(8) -0.0017(8) 0.0037(8) C18 0.0504(13) 0.0523(12) 0.0385(12) -0.0057(9) -0.0052(10) -0.0054(10) C19 0.0569(14) 0.0455(11) 0.0441(12) -0.0058(9) -0.0048(11) 0.0115(10) C20 0.0565(15) 0.0641(14) 0.0424(12) 0.0025(10) 0.0017(11) 0.0128(11) C21 0.0543(14) 0.0547(12) 0.0463(13) 0.0081(10) -0.0042(11) -0.0015(10) C22 0.0805(18) 0.0707(14) 0.0422(13) 0.0067(10) -0.0036(12) -0.0028(12) C23 0.0691(16) 0.0559(13) 0.0571(14) 0.0025(10) -0.0102(12) -0.0218(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 N1 C8 1.390(2) . ? N1 C17 1.384(2) . ? O C16 1.2329(19) . ? N3 C5 1.477(2) . ? N3 C12 1.452(2) . ? N3 C16 1.354(2) . ? C4 C8 1.408(2) . ? C4 C9 1.402(2) . ? C4 C10 1.427(2) . ? C5 C6 1.509(3) . ? C5 C17 1.499(2) . ? C6 C11 1.391(2) . ? C6 C13 1.379(2) . ? C7 C8 1.399(2) . ? C7 C18 1.381(2) . ? C7 C23 1.502(2) . ? C9 C14 1.376(3) . ? C10 C15 1.500(2) . ? C10 C17 1.364(2) . ? C11 C16 1.474(3) . ? C11 C19 1.382(3) . ? C12 C15 1.520(3) . ? C13 C21 1.383(3) . ? C14 C18 1.402(3) . ? C14 C22 1.513(3) . ? C19 C20 1.385(3) . ? C20 C21 1.390(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 C17 N1 C8 108.39(14) . . ? C12 N3 C5 119.72(14) . . ? C16 N3 C5 113.08(16) . . ? C16 N3 C12 123.98(15) . . ? C8 C4 C10 106.96(15) . . ? C9 C4 C8 119.16(16) . . ? C9 C4 C10 133.75(17) . . ? N3 C5 C6 101.77(13) . . ? N3 C5 C17 107.08(13) . . ? C17 C5 C6 116.41(16) . . ? C11 C6 C5 109.23(16) . . ? C13 C6 C5 130.71(16) . . ? C13 C6 C11 120.06(18) . . ? C8 C7 C23 122.33(16) . . ? C18 C7 C8 115.90(16) . . ? C18 C7 C23 121.73(17) . . ? N1 C8 C4 107.55(14) . . ? N1 C8 C7 130.29(16) . . ? C7 C8 C4 122.13(15) . . ? C14 C9 C4 120.03(17) . . ? C4 C10 C15 128.87(16) . . ? C17 C10 C4 107.56(15) . . ? C17 C10 C15 123.55(17) . . ? C6 C11 C16 108.77(17) . . ? C19 C11 C6 121.53(18) . . ? C19 C11 C16 129.66(16) . . ? N3 C12 C15 110.53(15) . . ? C6 C13 C21 118.41(18) . . ? C9 C14 C18 118.74(16) . . ? C9 C14 C22 121.41(18) . . ? C18 C14 C22 119.78(18) . . ? C10 C15 C12 110.45(15) . . ? O C16 N3 125.12(19) . . ? O C16 C11 127.93(17) . . ? N3 C16 C11 106.95(15) . . ? N1 C17 C5 125.86(15) . . ? C10 C17 N1 109.49(15) . . ? C10 C17 C5 124.58(15) . . ? C7 C18 C14 123.98(17) . . ? C11 C19 C20 118.51(18) . . ? C19 C20 C21 119.7(2) . . ? C13 C21 C20 121.7(2) . . ? data_crr-crr-311 _database_code_depnum_ccdc_archive 'CCDC 876036' _audit_creation_date 2011-10-31 _audit_creation_method ; Olex2 1.1 (compiled 2011.02.15 svn.r1672, GUI svn.r3494) ; _chemical_name_common 10-methyl-5,6,11,11b-tetrahydro-1H-indolizino[8,7-b]indol-3(2H)-one _chemical_name_systematic ; 10-methyl-5,6,11,11b-tetrahydro-1H-indolizino[8,7-b]indol-3(2H)-one ; _chemical_formula_moiety 'C15 H16 N2 O' _chemical_formula_sum 'C15 H16 N2 O' _chemical_formula_weight 240.12 _chemical_absolute_configuration unk _chemical_melting_point 551 _chemical_oxdiff_formula 'C15 H16 N2 O' _chemical_oxdiff_usercomment '300 K, BROWN, BLOCK, .48 .28 .28' 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 monoclinic _space_group_IT_number 9 _space_group_name_H-M_alt 'C 1 c 1' _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+1/2, y+1/2, z' 4 'x+1/2, -y+1/2, z+1/2' _cell_length_a 6.7583(3) _cell_length_b 17.8626(7) _cell_length_c 10.4574(5) _cell_angle_alpha 90.00 _cell_angle_beta 104.431(5) _cell_angle_gamma 90.00 _cell_volume 1222.60(9) _cell_formula_units_Z 4 _cell_measurement_reflns_used 3262 _cell_measurement_temperature 293(2) _cell_measurement_theta_max 29.3041 _cell_measurement_theta_min 3.0349 _exptl_absorpt_coefficient_mu 0.083 _exptl_absorpt_correction_T_max 1.00000 _exptl_absorpt_correction_T_min 0.79875 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details ; CrysAlisPro, Oxford Diffraction Ltd., Version 1.171.34.44 (release 25-10-2010 CrysAlis171 .NET) (compiled Oct 25 2010,18:11:34) Empirical absorption correction using spherical harmonics, implemented in SCALE3 ABSPACK scaling algorithm. ; _exptl_crystal_colour brown _exptl_crystal_density_diffrn 1.304 _exptl_crystal_density_meas ? _exptl_crystal_density_method 'not measured' _exptl_crystal_description ? _exptl_crystal_F_000 480 _exptl_crystal_size_max 0.48 _exptl_crystal_size_mid 0.28 _exptl_crystal_size_min 0.28 _exptl_special_details ; ? ; _diffrn_reflns_av_R_equivalents 0.0422 _diffrn_reflns_av_unetI/netI 0.0454 _diffrn_reflns_limit_h_max 8 _diffrn_reflns_limit_h_min -8 _diffrn_reflns_limit_k_max 21 _diffrn_reflns_limit_k_min -21 _diffrn_reflns_limit_l_max 12 _diffrn_reflns_limit_l_min -12 _diffrn_reflns_number 5496 _diffrn_reflns_theta_full 25.00 _diffrn_reflns_theta_max 25.00 _diffrn_reflns_theta_min 3.04 _diffrn_ambient_temperature 293(2) _diffrn_detector_area_resol_mean 15.9821 _diffrn_measured_fraction_theta_full 0.999 _diffrn_measured_fraction_theta_max 0.999 _diffrn_measurement_details ; #__ type_ start__ end____ width___ exp.time_ 1 omega -3.00 46.00 1.0000 15.0000 omega____ theta____ kappa____ phi______ frames - -17.4178 77.0000 -120.0000 49 #__ type_ start__ end____ width___ exp.time_ 2 omega -46.00 53.00 1.0000 15.0000 omega____ theta____ kappa____ phi______ frames - -17.4178 77.0000 120.0000 99 #__ type_ start__ end____ width___ exp.time_ 3 omega -9.00 87.00 1.0000 15.0000 omega____ theta____ kappa____ phi______ frames - 19.1366 77.0000 120.0000 96 #__ type_ start__ end____ width___ exp.time_ 4 omega 61.00 86.00 1.0000 15.0000 omega____ theta____ kappa____ phi______ frames - 19.1366 77.0000 30.0000 25 #__ type_ start__ end____ width___ exp.time_ 5 omega -11.00 80.00 1.0000 15.0000 omega____ theta____ kappa____ phi______ frames - 19.1366 77.0000 0.0000 91 #__ type_ start__ end____ width___ exp.time_ 6 omega -94.00 -32.00 1.0000 15.0000 omega____ theta____ kappa____ phi______ frames - -17.4178 179.0000 -90.0000 62 #__ type_ start__ end____ width___ exp.time_ 7 omega -11.00 89.00 1.0000 15.0000 omega____ theta____ kappa____ phi______ frames - 19.1366 77.0000 -120.0000 100 ; _diffrn_measurement_device_type 'Xcalibur, Eos' _diffrn_measurement_method '\w scans' _diffrn_orient_matrix_UB_11 -0.0499979000 _diffrn_orient_matrix_UB_12 0.0226166000 _diffrn_orient_matrix_UB_13 -0.0541678000 _diffrn_orient_matrix_UB_21 0.0747512000 _diffrn_orient_matrix_UB_22 -0.0099870000 _diffrn_orient_matrix_UB_23 -0.0340063000 _diffrn_orient_matrix_UB_31 -0.0604478000 _diffrn_orient_matrix_UB_32 -0.0310866000 _diffrn_orient_matrix_UB_33 -0.0285103000 _diffrn_radiation_monochromator graphite _diffrn_radiation_type 'Mo K\a' _diffrn_radiation_wavelength 0.7107 _diffrn_source 'Enhance (Mo) X-ray Source' _diffrn_standards_decay_% ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_number ? _reflns_number_gt 1713 _reflns_number_total 2109 _reflns_odcompleteness_completeness 99.77 _reflns_odcompleteness_iscentric 1 _reflns_odcompleteness_theta 26.32 _reflns_threshold_expression >2sigma(I) _computing_cell_refinement ; CrysAlisPro, Oxford Diffraction Ltd., Version 1.171.34.44 (release 25-10-2010 CrysAlis171 .NET) (compiled Oct 25 2010,18:11:34) ; _computing_data_collection ; CrysAlisPro, Oxford Diffraction Ltd., Version 1.171.34.44 (release 25-10-2010 CrysAlis171 .NET) (compiled Oct 25 2010,18:11:34) ; _computing_data_reduction ; CrysAlisPro, Oxford Diffraction Ltd., Version 1.171.34.44 (release 25-10-2010 CrysAlis171 .NET) (compiled Oct 25 2010,18:11:34) ; _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 0.138 _refine_diff_density_min -0.144 _refine_diff_density_rms 0.030 _refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881' _refine_ls_abs_structure_Flack -3.3(17) _refine_ls_extinction_coef ? _refine_ls_extinction_method none _refine_ls_goodness_of_fit_ref 1.003 _refine_ls_hydrogen_treatment constr _refine_ls_matrix_type full _refine_ls_number_parameters 164 _refine_ls_number_reflns 2109 _refine_ls_number_restraints 2 _refine_ls_R_factor_all 0.0529 _refine_ls_R_factor_gt 0.0381 _refine_ls_restrained_S_all 1.003 _refine_ls_shift/su_max 0.033 _refine_ls_shift/su_mean 0.001 _refine_ls_structure_factor_coef Fsqd _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0408P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_gt 0.0792 _refine_ls_wR_factor_ref 0.0844 _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 N N -0.4176(3) -0.39460(10) -0.79081(18) 0.0353(5) Uani 1 1 d . . . H H -0.3444 -0.3669 -0.8283 0.042 Uiso 1 1 calc R . . C2 C -0.4208(4) -0.47141(12) -0.7909(2) 0.0317(5) Uani 1 1 d . . . C3 C -0.6440(3) -0.42862(13) -0.6754(2) 0.0344(6) Uani 1 1 d . . . C4 C -0.5611(3) -0.49491(12) -0.7195(2) 0.0311(5) Uani 1 1 d . . . O O -0.7383(3) -0.21571(10) -0.42074(15) 0.0633(6) Uani 1 1 d . . . C6 C -0.5874(3) -0.28899(12) -0.6949(2) 0.0363(6) Uani 1 1 d . . . H6 H -0.6642 -0.2649 -0.7765 0.044 Uiso 1 1 calc R . . C7 C -0.5891(4) -0.57170(14) -0.7025(2) 0.0430(6) Uani 1 1 d . . . H7 H -0.6790 -0.5884 -0.6543 0.052 Uiso 1 1 calc R . . N0AA N -0.7063(3) -0.28668(10) -0.59530(18) 0.0404(5) Uani 1 1 d . . . C9 C -0.5516(3) -0.36951(12) -0.7205(2) 0.0321(5) Uani 1 1 d . . . C10 C -0.3418(4) -0.59667(13) -0.8272(3) 0.0476(7) Uani 1 1 d . . . H10 H -0.2688 -0.6322 -0.8616 0.057 Uiso 1 1 calc R . . C11 C -0.4811(4) -0.62170(13) -0.7584(3) 0.0493(6) Uani 1 1 d . . . H11 H -0.5012 -0.6728 -0.7503 0.059 Uiso 1 1 calc R . . C12 C -0.3062(4) -0.52209(13) -0.8469(2) 0.0373(6) Uani 1 1 d . . . C13 C -0.6538(4) -0.23001(13) -0.5096(2) 0.0440(6) Uani 1 1 d . . . C14 C -0.7935(3) -0.42040(14) -0.5942(2) 0.0388(6) Uani 1 1 d . . . H14A H -0.7294 -0.4334 -0.5032 0.047 Uiso 1 1 calc R . . H14B H -0.9075 -0.4542 -0.6262 0.047 Uiso 1 1 calc R . . C15 C -0.1575(4) -0.49589(14) -0.9218(3) 0.0518(7) Uani 1 1 d . . . H15A H -0.0509 -0.4676 -0.8642 0.078 Uiso 1 1 calc R . . H15B H -0.2269 -0.4649 -0.9941 0.078 Uiso 1 1 calc R . . H15C H -0.0993 -0.5384 -0.9552 0.078 Uiso 1 1 calc R . . C16 C -0.4821(4) -0.18773(14) -0.5437(2) 0.0477(7) Uani 1 1 d . . . H16A H -0.3773 -0.1752 -0.4649 0.057 Uiso 1 1 calc R . . H16B H -0.5314 -0.1420 -0.5912 0.057 Uiso 1 1 calc R . . C17 C -0.3999(4) -0.24182(13) -0.6309(3) 0.0492(7) Uani 1 1 d . . . H17A H -0.2914 -0.2727 -0.5786 0.059 Uiso 1 1 calc R . . H17B H -0.3490 -0.2151 -0.6969 0.059 Uiso 1 1 calc R . . C18 C -0.8711(4) -0.33968(14) -0.6012(3) 0.0481(7) Uani 1 1 d . . . H18A H -0.9753 -0.3325 -0.6828 0.058 Uiso 1 1 calc R . . H18B H -0.9328 -0.3305 -0.5282 0.058 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 N 0.0430(10) 0.0297(10) 0.0410(12) -0.0003(9) 0.0254(10) -0.0036(9) C2 0.0384(13) 0.0278(12) 0.0292(13) -0.0035(10) 0.0090(11) 0.0005(11) C3 0.0390(13) 0.0341(13) 0.0337(14) -0.0007(10) 0.0158(12) -0.0033(11) C4 0.0321(12) 0.0319(12) 0.0300(13) 0.0003(10) 0.0090(11) -0.0037(10) O 0.0980(15) 0.0510(11) 0.0522(12) -0.0073(8) 0.0399(12) 0.0195(11) C6 0.0448(14) 0.0323(12) 0.0358(13) -0.0001(10) 0.0178(12) 0.0032(10) C7 0.0492(15) 0.0352(13) 0.0457(15) 0.0017(11) 0.0142(13) -0.0103(11) N0AA 0.0428(12) 0.0372(11) 0.0473(12) -0.0058(9) 0.0227(11) 0.0044(9) C9 0.0377(13) 0.0301(12) 0.0321(14) -0.0028(10) 0.0154(12) 0.0013(11) C10 0.0523(17) 0.0366(15) 0.0496(17) -0.0077(12) 0.0043(15) 0.0126(13) C11 0.0622(16) 0.0292(13) 0.0538(15) 0.0024(13) 0.0094(14) 0.0009(13) C12 0.0374(14) 0.0406(14) 0.0336(14) -0.0049(11) 0.0084(12) 0.0048(12) C13 0.0566(16) 0.0384(14) 0.0375(14) 0.0002(12) 0.0126(14) 0.0167(13) C14 0.0350(12) 0.0487(15) 0.0382(14) -0.0035(11) 0.0193(12) -0.0073(11) C15 0.0501(17) 0.0605(18) 0.0509(18) -0.0065(14) 0.0239(15) 0.0065(14) C16 0.0598(16) 0.0354(14) 0.0455(16) -0.0067(11) 0.0085(14) 0.0029(13) C17 0.0549(16) 0.0343(12) 0.0645(17) -0.0081(12) 0.0265(14) -0.0028(12) C18 0.0362(12) 0.0592(16) 0.0548(17) -0.0039(13) 0.0223(13) 0.0032(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 N C2 1.372(3) . ? N C9 1.376(3) . ? C2 C4 1.409(3) . ? C2 C12 1.410(3) . ? C3 C4 1.434(3) . ? C3 C9 1.369(3) . ? C3 C14 1.481(3) . ? C4 C7 1.402(3) . ? O C13 1.233(2) . ? C6 N0AA 1.466(3) . ? C6 C9 1.494(3) . ? C6 C17 1.530(3) . ? C7 C11 1.373(4) . ? N0AA C13 1.340(3) . ? N0AA C18 1.451(3) . ? C10 C11 1.393(4) . ? C10 C12 1.378(3) . ? C12 C15 1.495(3) . ? C13 C16 1.500(3) . ? C14 C18 1.530(3) . ? C16 C17 1.524(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 N C9 108.29(17) . . ? N C2 C4 108.07(18) . . ? N C2 C12 129.20(19) . . ? C4 C2 C12 122.71(19) . . ? C4 C3 C14 130.04(19) . . ? C9 C3 C4 106.14(16) . . ? C9 C3 C14 123.8(2) . . ? C2 C4 C3 107.01(17) . . ? C7 C4 C2 119.26(19) . . ? C7 C4 C3 133.7(2) . . ? N0AA C6 C9 107.24(17) . . ? N0AA C6 C17 102.36(18) . . ? C9 C6 C17 117.08(19) . . ? C11 C7 C4 118.6(2) . . ? C13 N0AA C6 113.30(18) . . ? C13 N0AA C18 126.43(18) . . ? C18 N0AA C6 120.15(18) . . ? N C9 C6 124.54(18) . . ? C3 C9 N 110.50(18) . . ? C3 C9 C6 124.96(18) . . ? C12 C10 C11 123.6(2) . . ? C7 C11 C10 120.7(2) . . ? C2 C12 C15 121.8(2) . . ? C10 C12 C2 115.1(2) . . ? C10 C12 C15 123.1(2) . . ? O C13 N0AA 124.4(2) . . ? O C13 C16 127.3(2) . . ? N0AA C13 C16 108.24(19) . . ? C3 C14 C18 109.92(19) . . ? C13 C16 C17 104.0(2) . . ? C16 C17 C6 103.04(19) . . ? N0AA C18 C14 111.3(2) . . ? data_crr-crr-318 _database_code_depnum_ccdc_archive 'CCDC 876037' _audit_creation_date 2012-02-15 _audit_creation_method ; Olex2 1.1 (compiled 2011.02.15 svn.r1672, GUI svn.r3494) ; _chemical_name_common 2,3,4,4a,7,8,13b,13c-octahydro-1H-benzo[1,2]indolizino[8,7-b]indol-5(13H)-one _chemical_name_systematic ; 2,3,4,4a,7,8,13b,13c-octahydro-1H-benzo[1,2]indolizino[8,7-b]indol-5(13H)-one ; _chemical_formula_moiety 'C18 H20 N2 O' _chemical_formula_sum 'C18 H20 N2 O' _chemical_formula_weight 280.36 _chemical_melting_point 521 _chemical_oxdiff_formula 'C18 H20 N2 O1' _chemical_oxdiff_usercomment '300 K, RECTANGULAR BLOCK, .45 .35 .2' 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 monoclinic _space_group_IT_number 14 _space_group_name_H-M_alt 'P 1 21/n 1' _space_group_name_Hall '-P 2yn' loop_ _space_group_symop_id _space_group_symop_operation_xyz 1 'x, y, z' 2 '-x+1/2, y+1/2, -z+1/2' 3 '-x, -y, -z' 4 'x-1/2, -y-1/2, z-1/2' _cell_length_a 12.9129(5) _cell_length_b 12.3328(5) _cell_length_c 19.1436(9) _cell_angle_alpha 90.00 _cell_angle_beta 100.509(4) _cell_angle_gamma 90.00 _cell_volume 2997.5(2) _cell_formula_units_Z 8 _cell_measurement_reflns_used 8856 _cell_measurement_temperature 293(2) _cell_measurement_theta_max 29.2011 _cell_measurement_theta_min 2.7177 _exptl_absorpt_coefficient_mu 0.078 _exptl_absorpt_correction_T_max 1.00000 _exptl_absorpt_correction_T_min 0.63483 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details ; CrysAlisPro, Oxford Diffraction Ltd., Version 1.171.34.44 (release 25-10-2010 CrysAlis171 .NET) (compiled Oct 25 2010,18:11:34) Empirical absorption correction using spherical harmonics, implemented in SCALE3 ABSPACK scaling algorithm. ; _exptl_crystal_colour colourless _exptl_crystal_density_diffrn 1.242 _exptl_crystal_density_meas ? _exptl_crystal_density_method 'not measured' _exptl_crystal_description ? _exptl_crystal_F_000 1200 _exptl_crystal_size_max 0.45 _exptl_crystal_size_mid 0.35 _exptl_crystal_size_min 0.2 _exptl_special_details ; ? ; _diffrn_reflns_av_R_equivalents 0.0529 _diffrn_reflns_av_unetI/netI 0.0356 _diffrn_reflns_limit_h_max 15 _diffrn_reflns_limit_h_min -15 _diffrn_reflns_limit_k_max 14 _diffrn_reflns_limit_k_min -14 _diffrn_reflns_limit_l_max 22 _diffrn_reflns_limit_l_min -22 _diffrn_reflns_number 33349 _diffrn_reflns_theta_full 25.00 _diffrn_reflns_theta_max 25.00 _diffrn_reflns_theta_min 2.72 _diffrn_ambient_temperature 293(2) _diffrn_detector_area_resol_mean 15.9821 _diffrn_measured_fraction_theta_full 0.999 _diffrn_measured_fraction_theta_max 0.999 _diffrn_measurement_details ; #__ type_ start__ end____ width___ exp.time_ 1 omega -15.00 11.00 1.0000 10.0000 omega____ theta____ kappa____ phi______ frames - -17.5741 37.0000 120.0000 26 #__ type_ start__ end____ width___ exp.time_ 2 omega -75.00 -34.00 1.0000 10.0000 omega____ theta____ kappa____ phi______ frames - -17.5741 179.0000 90.0000 41 #__ type_ start__ end____ width___ exp.time_ 3 omega -90.00 8.00 1.0000 10.0000 omega____ theta____ kappa____ phi______ frames - -17.5741 -37.0000 120.0000 98 #__ type_ start__ end____ width___ exp.time_ 4 omega -79.00 -36.00 1.0000 10.0000 omega____ theta____ kappa____ phi______ frames - -17.5741 179.0000 60.0000 43 #__ type_ start__ end____ width___ exp.time_ 5 omega 30.00 55.00 1.0000 10.0000 omega____ theta____ kappa____ phi______ frames - -17.5741 37.0000 120.0000 25 #__ type_ start__ end____ width___ exp.time_ 6 omega 14.00 83.00 1.0000 10.0000 omega____ theta____ kappa____ phi______ frames - 19.2928 77.0000 -60.0000 69 #__ type_ start__ end____ width___ exp.time_ 7 omega 56.00 82.00 1.0000 10.0000 omega____ theta____ kappa____ phi______ frames - 19.2928 -139.0000 136.0000 26 #__ type_ start__ end____ width___ exp.time_ 8 omega 1.00 78.00 1.0000 10.0000 omega____ theta____ kappa____ phi______ frames - 19.2928 -130.0000 -49.0000 77 #__ type_ start__ end____ width___ exp.time_ 9 omega -7.00 89.00 1.0000 10.0000 omega____ theta____ kappa____ phi______ frames - 19.2928 77.0000 60.0000 96 #__ type_ start__ end____ width___ exp.time_ 10 omega -88.00 0.00 1.0000 10.0000 omega____ theta____ kappa____ phi______ frames - -17.5741 -77.0000 -90.0000 88 #__ type_ start__ end____ width___ exp.time_ 11 omega -94.00 -32.00 1.0000 10.0000 omega____ theta____ kappa____ phi______ frames - -17.5741 179.0000 -90.0000 62 ; _diffrn_measurement_device_type 'Xcalibur, Eos' _diffrn_measurement_method '\w scans' _diffrn_orient_matrix_UB_11 0.0030802000 _diffrn_orient_matrix_UB_12 -0.0004125000 _diffrn_orient_matrix_UB_13 -0.0366160000 _diffrn_orient_matrix_UB_21 -0.0549378000 _diffrn_orient_matrix_UB_22 0.0098198000 _diffrn_orient_matrix_UB_23 -0.0088193000 _diffrn_orient_matrix_UB_31 0.0095789000 _diffrn_orient_matrix_UB_32 0.0566998000 _diffrn_orient_matrix_UB_33 0.0012870000 _diffrn_radiation_monochromator graphite _diffrn_radiation_type 'Mo K\a' _diffrn_radiation_wavelength 0.7107 _diffrn_source 'Enhance (Mo) X-ray Source' _diffrn_standards_decay_% ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_number ? _reflns_number_gt 3665 _reflns_number_total 5268 _reflns_odcompleteness_completeness 99.83 _reflns_odcompleteness_iscentric 1 _reflns_odcompleteness_theta 26.32 _reflns_threshold_expression >2sigma(I) _computing_cell_refinement ; CrysAlisPro, Oxford Diffraction Ltd., Version 1.171.34.44 (release 25-10-2010 CrysAlis171 .NET) (compiled Oct 25 2010,18:11:34) ; _computing_data_collection ; CrysAlisPro, Oxford Diffraction Ltd., Version 1.171.34.44 (release 25-10-2010 CrysAlis171 .NET) (compiled Oct 25 2010,18:11:34) ; _computing_data_reduction ; CrysAlisPro, Oxford Diffraction Ltd., Version 1.171.34.44 (release 25-10-2010 CrysAlis171 .NET) (compiled Oct 25 2010,18:11:34) ; _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 0.140 _refine_diff_density_min -0.170 _refine_diff_density_rms 0.033 _refine_ls_extinction_coef ? _refine_ls_extinction_method none _refine_ls_goodness_of_fit_ref 1.026 _refine_ls_hydrogen_treatment mixed _refine_ls_matrix_type full _refine_ls_number_parameters 387 _refine_ls_number_reflns 5268 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0744 _refine_ls_R_factor_gt 0.0451 _refine_ls_restrained_S_all 1.026 _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^)+(0.0432P)^2^+0.4906P] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_gt 0.0970 _refine_ls_wR_factor_ref 0.1104 _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 O O 0.37050(10) 0.11645(11) 0.22385(7) 0.0544(4) Uani 1 1 d . . . N N 0.50930(11) 0.00034(12) 0.22468(7) 0.0430(4) Uani 1 1 d . . . N3 N 0.43188(12) -0.49794(12) 0.19286(8) 0.0512(4) Uani 1 1 d . . . C4 C 0.69947(13) -0.02591(14) 0.18001(9) 0.0405(4) Uani 1 1 d . . . N5 N 0.23076(12) -0.71497(13) 0.16240(9) 0.0492(4) Uani 1 1 d . . . N0AA N 0.67098(12) -0.20045(14) 0.14793(9) 0.0477(4) Uani 1 1 d . . . C7 C 0.52796(13) -0.10920(14) 0.19991(9) 0.0414(4) Uani 1 1 d . . . H7 H 0.5265 -0.1619 0.2380 0.050 Uiso 1 1 calc R . . O0AA O 0.57115(12) -0.39808(12) 0.17068(8) 0.0770(5) Uani 1 1 d . . . C9 C 0.78634(13) -0.06301(15) 0.14914(9) 0.0429(4) Uani 1 1 d . . . C10 C 0.40711(14) 0.02808(16) 0.21037(9) 0.0429(4) Uani 1 1 d . . . C11 C 0.63235(13) -0.11119(14) 0.17769(9) 0.0396(4) Uani 1 1 d . . . C12 C 0.28616(14) -0.61889(15) 0.16751(10) 0.0449(5) Uani 1 1 d . . . C13 C 0.12711(14) -0.69225(16) 0.13293(10) 0.0500(5) Uani 1 1 d . . . C14 C 0.76618(13) -0.17232(16) 0.12982(9) 0.0453(5) Uani 1 1 d . . . C15 C 0.22134(15) -0.53469(15) 0.14338(10) 0.0495(5) Uani 1 1 d . . . C16 C 0.11872(15) -0.57977(16) 0.12077(10) 0.0518(5) Uani 1 1 d . . . C17 C 0.43077(12) -0.12429(14) 0.14084(9) 0.0418(4) Uani 1 1 d . . . H17 H 0.4144 -0.2014 0.1330 0.050 Uiso 1 1 calc R . . C18 C 0.57522(14) -0.59754(16) 0.17325(10) 0.0500(5) Uani 1 1 d . . . H18 H 0.6089 -0.6187 0.2214 0.060 Uiso 1 1 calc R . . C19 C 0.87916(14) -0.01542(18) 0.13605(10) 0.0563(5) Uani 1 1 d . . . H19 H 0.8947 0.0565 0.1484 0.068 Uiso 1 1 calc R . . C20 C 0.43490(14) -0.66392(17) 0.07306(10) 0.0511(5) Uani 1 1 d . . . H20A H 0.3795 -0.7174 0.0608 0.061 Uiso 1 1 calc R . . H20B H 0.4049 -0.5930 0.0602 0.061 Uiso 1 1 calc R . . C21 C 0.52878(16) -0.48581(17) 0.17805(10) 0.0530(5) Uani 1 1 d . . . C22 C 0.34635(13) -0.06806(15) 0.17449(10) 0.0456(5) Uani 1 1 d . . . H22 H 0.3293 -0.1158 0.2117 0.055 Uiso 1 1 calc R . . C23 C 0.47602(13) -0.66739(15) 0.15266(9) 0.0428(4) Uani 1 1 d . . . H23 H 0.4901 -0.7423 0.1687 0.051 Uiso 1 1 calc R . . C24 C 0.44289(13) -0.06893(16) 0.07163(9) 0.0464(5) Uani 1 1 d . . . H24A H 0.4734 0.0024 0.0820 0.056 Uiso 1 1 calc R . . H24B H 0.4907 -0.1108 0.0486 0.056 Uiso 1 1 calc R . . C25 C 0.40095(14) -0.61178(14) 0.19566(10) 0.0450(5) Uani 1 1 d . . . H25 H 0.4158 -0.6374 0.2449 0.054 Uiso 1 1 calc R . . C26 C 0.59589(14) 0.06876(16) 0.25804(10) 0.0518(5) Uani 1 1 d . . . H26A H 0.6293 0.0367 0.3028 0.062 Uiso 1 1 calc R . . H26B H 0.5690 0.1394 0.2680 0.062 Uiso 1 1 calc R . . C27 C 0.25985(18) -0.41986(15) 0.14581(12) 0.0625(6) Uani 1 1 d . . . H27A H 0.2064 -0.3716 0.1577 0.075 Uiso 1 1 calc R . . H27B H 0.2742 -0.3989 0.0997 0.075 Uiso 1 1 calc R . . C28 C 0.67681(14) 0.08171(15) 0.20989(11) 0.0520(5) Uani 1 1 d . . . H28A H 0.6501 0.1313 0.1715 0.062 Uiso 1 1 calc R . . H28B H 0.7413 0.1120 0.2368 0.062 Uiso 1 1 calc R . . C29 C 0.83471(16) -0.23340(18) 0.09769(11) 0.0613(6) Uani 1 1 d . . . H29 H 0.8202 -0.3053 0.0848 0.074 Uiso 1 1 calc R . . C30 C 0.33757(15) -0.0579(2) 0.02146(11) 0.0656(6) Uani 1 1 d . . . H30A H 0.3480 -0.0239 -0.0224 0.079 Uiso 1 1 calc R . . H30B H 0.3073 -0.1291 0.0102 0.079 Uiso 1 1 calc R . . C31 C 0.04151(16) -0.76106(19) 0.11622(12) 0.0654(6) Uani 1 1 d . . . H31 H 0.0481 -0.8353 0.1244 0.078 Uiso 1 1 calc R . . C32 C 0.35948(19) -0.41104(16) 0.20135(12) 0.0655(6) Uani 1 1 d . . . H32A H 0.3930 -0.3416 0.1967 0.079 Uiso 1 1 calc R . . H32B H 0.3418 -0.4148 0.2484 0.079 Uiso 1 1 calc R . . C33 C 0.52149(16) -0.6865(2) 0.03117(11) 0.0698(6) Uani 1 1 d . . . H33A H 0.4926 -0.6836 -0.0193 0.084 Uiso 1 1 calc R . . H33B H 0.5493 -0.7588 0.0422 0.084 Uiso 1 1 calc R . . C34 C 0.24443(14) -0.04143(19) 0.12433(11) 0.0612(6) Uani 1 1 d . . . H34A H 0.2041 -0.1075 0.1131 0.073 Uiso 1 1 calc R . . H34B H 0.2031 0.0075 0.1480 0.073 Uiso 1 1 calc R . . C35 C 0.94676(16) -0.0760(2) 0.10480(12) 0.0691(6) Uani 1 1 d . . . H35 H 1.0087 -0.0446 0.0962 0.083 Uiso 1 1 calc R . . C36 C 0.92519(16) -0.1831(2) 0.08561(12) 0.0730(7) Uani 1 1 d . . . H36 H 0.9727 -0.2218 0.0641 0.088 Uiso 1 1 calc R . . C37 C 0.26283(16) 0.0104(2) 0.05601(11) 0.0707(7) Uani 1 1 d . . . H37A H 0.2924 0.0823 0.0660 0.085 Uiso 1 1 calc R . . H37B H 0.1962 0.0179 0.0235 0.085 Uiso 1 1 calc R . . C38 C 0.65766(15) -0.60672(18) 0.12638(11) 0.0629(6) Uani 1 1 d . . . H38A H 0.7074 -0.5474 0.1370 0.075 Uiso 1 1 calc R . . H38B H 0.6962 -0.6740 0.1370 0.075 Uiso 1 1 calc R . . C39 C -0.06455(19) -0.6045(3) 0.07492(13) 0.0827(8) Uani 1 1 d . . . H39 H -0.1302 -0.5761 0.0554 0.099 Uiso 1 1 calc R . . C40 C 0.02042(18) -0.5366(2) 0.09147(12) 0.0698(7) Uani 1 1 d . . . H40 H 0.0127 -0.4624 0.0833 0.084 Uiso 1 1 calc R . . C41 C 0.60992(16) -0.6041(2) 0.04876(12) 0.0726(7) Uani 1 1 d . . . H41A H 0.6639 -0.6196 0.0210 0.087 Uiso 1 1 calc R . . H41B H 0.5826 -0.5321 0.0361 0.087 Uiso 1 1 calc R . . C42 C -0.05368(17) -0.7154(2) 0.08702(13) 0.0802(7) Uani 1 1 d . . . H42 H -0.1124 -0.7599 0.0750 0.096 Uiso 1 1 calc R . . H5 H 0.2619(15) -0.7805(16) 0.1774(11) 0.066(6) Uiso 1 1 d . . . H0A H 0.6449(15) -0.2651(16) 0.1469(11) 0.066(7) Uiso 1 1 d . . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 O 0.0515(8) 0.0569(9) 0.0567(9) -0.0003(7) 0.0151(6) 0.0070(7) N 0.0359(8) 0.0508(10) 0.0406(9) -0.0019(7) 0.0022(6) -0.0015(7) N3 0.0604(10) 0.0432(10) 0.0546(10) -0.0070(7) 0.0227(8) -0.0152(8) C4 0.0334(9) 0.0426(11) 0.0419(10) 0.0062(8) -0.0023(8) -0.0038(8) N5 0.0416(9) 0.0408(10) 0.0683(11) 0.0054(8) 0.0183(8) -0.0041(8) N0AA 0.0408(9) 0.0389(10) 0.0635(11) 0.0028(8) 0.0093(8) -0.0017(8) C7 0.0390(10) 0.0406(11) 0.0442(10) 0.0077(8) 0.0064(8) -0.0015(8) O0AA 0.0823(11) 0.0614(10) 0.0898(12) -0.0038(8) 0.0226(9) -0.0387(9) C9 0.0313(9) 0.0521(12) 0.0408(10) 0.0113(9) -0.0053(8) -0.0027(8) C10 0.0432(11) 0.0530(13) 0.0345(10) 0.0063(8) 0.0124(8) 0.0028(9) C11 0.0334(9) 0.0414(11) 0.0420(10) 0.0077(8) 0.0017(8) 0.0002(8) C12 0.0479(11) 0.0420(11) 0.0502(11) 0.0001(9) 0.0232(9) -0.0054(9) C13 0.0417(11) 0.0577(13) 0.0549(12) 0.0043(10) 0.0203(9) 0.0007(10) C14 0.0344(10) 0.0529(12) 0.0463(11) 0.0114(9) 0.0012(8) 0.0040(9) C15 0.0576(12) 0.0429(11) 0.0554(12) 0.0067(9) 0.0301(10) 0.0035(10) C16 0.0492(12) 0.0609(14) 0.0505(12) 0.0100(10) 0.0230(9) 0.0067(10) C17 0.0327(9) 0.0429(11) 0.0496(11) -0.0010(8) 0.0070(8) -0.0066(8) C18 0.0443(11) 0.0618(14) 0.0426(11) 0.0034(9) 0.0043(8) -0.0169(10) C19 0.0352(11) 0.0721(15) 0.0580(13) 0.0133(10) -0.0008(9) -0.0085(10) C20 0.0420(10) 0.0608(13) 0.0494(12) -0.0131(9) 0.0054(9) -0.0098(9) C21 0.0602(13) 0.0551(14) 0.0430(11) -0.0049(9) 0.0080(9) -0.0257(11) C22 0.0375(10) 0.0549(12) 0.0461(11) 0.0043(9) 0.0122(8) -0.0068(9) C23 0.0370(10) 0.0433(11) 0.0488(11) 0.0019(8) 0.0095(8) -0.0067(8) C24 0.0405(10) 0.0599(13) 0.0392(10) -0.0040(9) 0.0082(8) -0.0020(9) C25 0.0527(11) 0.0415(11) 0.0432(11) 0.0016(8) 0.0150(9) -0.0117(9) C26 0.0479(11) 0.0557(13) 0.0478(12) -0.0067(9) -0.0016(9) -0.0012(10) C27 0.0803(16) 0.0439(12) 0.0741(15) 0.0090(10) 0.0427(13) 0.0045(11) C28 0.0412(10) 0.0494(12) 0.0609(13) -0.0019(9) -0.0029(9) -0.0088(9) C29 0.0537(13) 0.0619(14) 0.0683(14) 0.0073(11) 0.0111(11) 0.0154(11) C30 0.0515(12) 0.0994(18) 0.0434(12) -0.0020(11) 0.0015(10) 0.0046(12) C31 0.0464(12) 0.0748(16) 0.0765(16) 0.0036(12) 0.0153(11) -0.0126(11) C32 0.0959(17) 0.0404(12) 0.0707(15) -0.0084(10) 0.0428(14) -0.0118(12) C33 0.0619(14) 0.0978(18) 0.0513(13) -0.0187(12) 0.0143(11) 0.0036(13) C34 0.0332(10) 0.0838(16) 0.0661(14) -0.0124(12) 0.0075(9) 0.0012(10) C35 0.0386(12) 0.095(2) 0.0746(16) 0.0207(14) 0.0122(11) -0.0027(12) C36 0.0463(13) 0.100(2) 0.0766(16) 0.0165(14) 0.0209(11) 0.0207(13) C37 0.0509(13) 0.0983(19) 0.0568(14) 0.0028(12) -0.0064(10) 0.0191(12) C38 0.0407(11) 0.0809(16) 0.0674(15) 0.0050(11) 0.0106(10) -0.0124(11) C39 0.0511(14) 0.117(2) 0.0816(18) 0.0226(16) 0.0164(12) 0.0143(15) C40 0.0619(15) 0.0832(17) 0.0707(16) 0.0217(12) 0.0288(12) 0.0188(13) C41 0.0545(13) 0.107(2) 0.0627(15) 0.0046(13) 0.0279(11) -0.0037(13) C42 0.0472(14) 0.111(2) 0.0832(18) 0.0043(15) 0.0136(12) -0.0123(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 O C10 1.234(2) . ? N C7 1.466(2) . ? N C10 1.342(2) . ? N C26 1.452(2) . ? N3 C21 1.341(2) . ? N3 C25 1.463(2) . ? N3 C32 1.451(2) . ? C4 C9 1.435(2) . ? C4 C11 1.358(2) . ? C4 C28 1.495(2) . ? N5 C12 1.378(2) . ? N5 C13 1.383(2) . ? N5 H5 0.92(2) . ? N0AA C11 1.374(2) . ? N0AA C14 1.381(2) . ? N0AA H0A 0.86(2) . ? C7 H7 0.9800 . ? C7 C11 1.486(2) . ? C7 C17 1.540(2) . ? O0AA C21 1.232(2) . ? C9 C14 1.410(3) . ? C9 C19 1.398(2) . ? C10 C22 1.515(3) . ? C12 C15 1.361(2) . ? C12 C25 1.485(2) . ? C13 C16 1.408(3) . ? C13 C31 1.384(3) . ? C14 C29 1.388(3) . ? C15 C16 1.429(3) . ? C15 C27 1.499(3) . ? C16 C40 1.397(3) . ? C17 H17 0.9800 . ? C17 C22 1.530(2) . ? C17 C24 1.524(2) . ? C18 H18 0.9800 . ? C18 C21 1.512(3) . ? C18 C23 1.534(2) . ? C18 C38 1.516(3) . ? C19 H19 0.9300 . ? C19 C35 1.367(3) . ? C20 H20A 0.9700 . ? C20 H20B 0.9700 . ? C20 C23 1.520(2) . ? C20 C33 1.516(3) . ? C22 H22 0.9800 . ? C22 C34 1.517(2) . ? C23 H23 0.9800 . ? C23 C25 1.542(2) . ? C24 H24A 0.9700 . ? C24 H24B 0.9700 . ? C24 C30 1.521(2) . ? C25 H25 0.9800 . ? C26 H26A 0.9700 . ? C26 H26B 0.9700 . ? C26 C28 1.523(3) . ? C27 H27A 0.9700 . ? C27 H27B 0.9700 . ? C27 C32 1.516(3) . ? C28 H28A 0.9700 . ? C28 H28B 0.9700 . ? C29 H29 0.9300 . ? C29 C36 1.379(3) . ? C30 H30A 0.9700 . ? C30 H30B 0.9700 . ? C30 C37 1.520(3) . ? C31 H31 0.9300 . ? C31 C42 1.375(3) . ? C32 H32A 0.9700 . ? C32 H32B 0.9700 . ? C33 H33A 0.9700 . ? C33 H33B 0.9700 . ? C33 C41 1.520(3) . ? C34 H34A 0.9700 . ? C34 H34B 0.9700 . ? C34 C37 1.513(3) . ? C35 H35 0.9300 . ? C35 C36 1.385(3) . ? C36 H36 0.9300 . ? C37 H37A 0.9700 . ? C37 H37B 0.9700 . ? C38 H38A 0.9700 . ? C38 H38B 0.9700 . ? C38 C41 1.502(3) . ? C39 H39 0.9300 . ? C39 C40 1.371(3) . ? C39 C42 1.390(3) . ? C40 H40 0.9300 . ? C41 H41A 0.9700 . ? C41 H41B 0.9700 . ? C42 H42 0.9300 . ? 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 N C7 112.47(14) . . ? C10 N C26 126.23(16) . . ? C26 N C7 121.25(14) . . ? C21 N3 C25 112.72(16) . . ? C21 N3 C32 125.91(16) . . ? C32 N3 C25 121.26(15) . . ? C9 C4 C28 131.52(16) . . ? C11 C4 C9 106.36(15) . . ? C11 C4 C28 122.12(16) . . ? C12 N5 C13 107.81(16) . . ? C12 N5 H5 122.6(12) . . ? C13 N5 H5 129.6(12) . . ? C11 N0AA C14 108.06(16) . . ? C11 N0AA H0A 125.3(13) . . ? C14 N0AA H0A 126.0(13) . . ? N C7 H7 110.1 . . ? N C7 C11 108.60(14) . . ? N C7 C17 100.89(13) . . ? C11 C7 H7 110.1 . . ? C11 C7 C17 116.63(15) . . ? C17 C7 H7 110.1 . . ? C14 C9 C4 107.00(15) . . ? C19 C9 C4 134.46(18) . . ? C19 C9 C14 118.55(18) . . ? O C10 N 125.62(17) . . ? O C10 C22 126.83(16) . . ? N C10 C22 107.55(16) . . ? C4 C11 N0AA 110.86(16) . . ? C4 C11 C7 125.77(16) . . ? N0AA C11 C7 123.28(15) . . ? N5 C12 C25 123.19(16) . . ? C15 C12 N5 110.66(17) . . ? C15 C12 C25 126.14(16) . . ? N5 C13 C16 107.87(16) . . ? N5 C13 C31 130.00(19) . . ? C31 C13 C16 122.14(18) . . ? N0AA C14 C9 107.72(16) . . ? N0AA C14 C29 130.05(19) . . ? C29 C14 C9 122.22(17) . . ? C12 C15 C16 106.55(16) . . ? C12 C15 C27 122.04(18) . . ? C16 C15 C27 131.37(18) . . ? C13 C16 C15 107.10(16) . . ? C40 C16 C13 118.65(19) . . ? C40 C16 C15 134.2(2) . . ? C7 C17 H17 110.8 . . ? C22 C17 C7 100.60(14) . . ? C22 C17 H17 110.8 . . ? C24 C17 C7 112.66(14) . . ? C24 C17 H17 110.8 . . ? C24 C17 C22 110.92(15) . . ? C21 C18 H18 107.3 . . ? C21 C18 C23 101.86(15) . . ? C21 C18 C38 115.66(16) . . ? C23 C18 H18 107.3 . . ? C38 C18 H18 107.3 . . ? C38 C18 C23 116.71(16) . . ? C9 C19 H19 120.5 . . ? C35 C19 C9 119.1(2) . . ? C35 C19 H19 120.5 . . ? H20A C20 H20B 108.0 . . ? C23 C20 H20A 109.3 . . ? C23 C20 H20B 109.3 . . ? C33 C20 H20A 109.3 . . ? C33 C20 H20B 109.3 . . ? C33 C20 C23 111.63(15) . . ? N3 C21 C18 107.87(16) . . ? O0AA C21 N3 125.0(2) . . ? O0AA C21 C18 127.15(19) . . ? C10 C22 C17 101.29(13) . . ? C10 C22 H22 107.8 . . ? C10 C22 C34 115.80(16) . . ? C17 C22 H22 107.8 . . ? C34 C22 C17 115.73(15) . . ? C34 C22 H22 107.8 . . ? C18 C23 H23 110.5 . . ? C18 C23 C25 100.94(14) . . ? C20 C23 C18 111.36(14) . . ? C20 C23 H23 110.5 . . ? C20 C23 C25 112.57(15) . . ? C25 C23 H23 110.5 . . ? C17 C24 H24A 109.3 . . ? C17 C24 H24B 109.3 . . ? H24A C24 H24B 108.0 . . ? C30 C24 C17 111.56(15) . . ? C30 C24 H24A 109.3 . . ? C30 C24 H24B 109.3 . . ? N3 C25 C12 107.73(15) . . ? N3 C25 C23 101.82(13) . . ? N3 C25 H25 109.8 . . ? C12 C25 C23 117.58(15) . . ? C12 C25 H25 109.8 . . ? C23 C25 H25 109.8 . . ? N C26 H26A 109.5 . . ? N C26 H26B 109.5 . . ? N C26 C28 110.67(14) . . ? H26A C26 H26B 108.1 . . ? C28 C26 H26A 109.5 . . ? C28 C26 H26B 109.5 . . ? C15 C27 H27A 109.9 . . ? C15 C27 H27B 109.9 . . ? C15 C27 C32 108.90(17) . . ? H27A C27 H27B 108.3 . . ? C32 C27 H27A 109.9 . . ? C32 C27 H27B 109.9 . . ? C4 C28 C26 110.01(15) . . ? C4 C28 H28A 109.7 . . ? C4 C28 H28B 109.7 . . ? C26 C28 H28A 109.7 . . ? C26 C28 H28B 109.7 . . ? H28A C28 H28B 108.2 . . ? C14 C29 H29 121.4 . . ? C36 C29 C14 117.3(2) . . ? C36 C29 H29 121.4 . . ? C24 C30 H30A 109.7 . . ? C24 C30 H30B 109.7 . . ? H30A C30 H30B 108.2 . . ? C37 C30 C24 109.90(16) . . ? C37 C30 H30A 109.7 . . ? C37 C30 H30B 109.7 . . ? C13 C31 H31 121.3 . . ? C42 C31 C13 117.4(2) . . ? C42 C31 H31 121.3 . . ? N3 C32 C27 110.50(16) . . ? N3 C32 H32A 109.5 . . ? N3 C32 H32B 109.5 . . ? C27 C32 H32A 109.5 . . ? C27 C32 H32B 109.5 . . ? H32A C32 H32B 108.1 . . ? C20 C33 H33A 109.5 . . ? C20 C33 H33B 109.5 . . ? C20 C33 C41 110.91(17) . . ? H33A C33 H33B 108.0 . . ? C41 C33 H33A 109.5 . . ? C41 C33 H33B 109.5 . . ? C22 C34 H34A 109.1 . . ? C22 C34 H34B 109.1 . . ? H34A C34 H34B 107.8 . . ? C37 C34 C22 112.57(15) . . ? C37 C34 H34A 109.1 . . ? C37 C34 H34B 109.1 . . ? C19 C35 H35 119.2 . . ? C19 C35 C36 121.6(2) . . ? C36 C35 H35 119.2 . . ? C29 C36 C35 121.3(2) . . ? C29 C36 H36 119.3 . . ? C35 C36 H36 119.3 . . ? C30 C37 H37A 109.5 . . ? C30 C37 H37B 109.5 . . ? C34 C37 C30 110.75(19) . . ? C34 C37 H37A 109.5 . . ? C34 C37 H37B 109.5 . . ? H37A C37 H37B 108.1 . . ? C18 C38 H38A 109.2 . . ? C18 C38 H38B 109.2 . . ? H38A C38 H38B 107.9 . . ? C41 C38 C18 112.21(16) . . ? C41 C38 H38A 109.2 . . ? C41 C38 H38B 109.2 . . ? C40 C39 H39 119.6 . . ? C40 C39 C42 120.7(2) . . ? C42 C39 H39 119.6 . . ? C16 C40 H40 120.3 . . ? C39 C40 C16 119.3(2) . . ? C39 C40 H40 120.3 . . ? C33 C41 H41A 109.4 . . ? C33 C41 H41B 109.4 . . ? C38 C41 C33 111.16(18) . . ? C38 C41 H41A 109.4 . . ? C38 C41 H41B 109.4 . . ? H41A C41 H41B 108.0 . . ? C31 C42 C39 121.7(2) . . ? C31 C42 H42 119.1 . . ? C39 C42 H42 119.1 . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag O C10 C22 C17 153.22(17) . . . . ? O C10 C22 C34 27.2(3) . . . . ? N C7 C11 C4 0.1(2) . . . . ? N C7 C11 N0AA -176.15(15) . . . . ? N C7 C17 C22 -38.03(15) . . . . ? N C7 C17 C24 80.13(17) . . . . ? N C10 C22 C17 -26.31(17) . . . . ? N C10 C22 C34 -152.34(15) . . . . ? N C26 C28 C4 -45.5(2) . . . . ? C4 C9 C14 N0AA 0.18(19) . . . . ? C4 C9 C14 C29 179.51(17) . . . . ? C4 C9 C19 C35 180.00(19) . . . . ? N5 C12 C15 C16 -0.7(2) . . . . ? N5 C12 C15 C27 177.21(16) . . . . ? N5 C12 C25 N3 179.90(15) . . . . ? N5 C12 C25 C23 65.7(2) . . . . ? N5 C13 C16 C15 0.5(2) . . . . ? N5 C13 C16 C40 -179.51(17) . . . . ? N5 C13 C31 C42 180.0(2) . . . . ? N0AA C14 C29 C36 179.70(19) . . . . ? C7 N C10 O -178.04(16) . . . . ? C7 N C10 C22 1.50(19) . . . . ? C7 N C26 C28 55.4(2) . . . . ? C7 C17 C22 C10 39.04(16) . . . . ? C7 C17 C22 C34 165.12(16) . . . . ? C7 C17 C24 C30 -164.33(16) . . . . ? C9 C4 C11 N0AA 0.48(19) . . . . ? C9 C4 C11 C7 -176.16(16) . . . . ? C9 C4 C28 C26 -160.56(17) . . . . ? C9 C14 C29 C36 0.5(3) . . . . ? C9 C19 C35 C36 0.3(3) . . . . ? C10 N C7 C11 146.86(14) . . . . ? C10 N C7 C17 23.74(18) . . . . ? C10 N C26 C28 -121.89(18) . . . . ? C10 C22 C34 C37 72.1(2) . . . . ? C11 C4 C9 C14 -0.40(18) . . . . ? C11 C4 C9 C19 179.87(19) . . . . ? C11 C4 C28 C26 20.0(2) . . . . ? C11 N0AA C14 C9 0.11(19) . . . . ? C11 N0AA C14 C29 -179.15(18) . . . . ? C11 C7 C17 C22 -155.41(15) . . . . ? C11 C7 C17 C24 -37.3(2) . . . . ? C12 N5 C13 C16 -0.9(2) . . . . ? C12 N5 C13 C31 179.01(19) . . . . ? C12 C15 C16 C13 0.1(2) . . . . ? C12 C15 C16 C40 -179.9(2) . . . . ? C12 C15 C27 C32 -21.5(2) . . . . ? C13 N5 C12 C15 1.0(2) . . . . ? C13 N5 C12 C25 -178.88(16) . . . . ? C13 C16 C40 C39 -0.5(3) . . . . ? C13 C31 C42 C39 -0.4(3) . . . . ? C14 N0AA C11 C4 -0.4(2) . . . . ? C14 N0AA C11 C7 176.36(15) . . . . ? C14 C9 C19 C35 0.3(3) . . . . ? C14 C29 C36 C35 0.1(3) . . . . ? C15 C12 C25 N3 0.0(2) . . . . ? C15 C12 C25 C23 -114.1(2) . . . . ? C15 C16 C40 C39 179.5(2) . . . . ? C15 C27 C32 N3 47.6(2) . . . . ? C16 C13 C31 C42 -0.1(3) . . . . ? C16 C15 C27 C32 155.76(19) . . . . ? C17 C7 C11 C4 113.16(19) . . . . ? C17 C7 C11 N0AA -63.1(2) . . . . ? C17 C22 C34 C37 -46.2(2) . . . . ? C17 C24 C30 C37 60.6(2) . . . . ? C18 C23 C25 N3 34.83(17) . . . . ? C18 C23 C25 C12 152.24(15) . . . . ? C18 C38 C41 C33 -51.7(3) . . . . ? C19 C9 C14 N0AA 179.96(15) . . . . ? C19 C9 C14 C29 -0.7(3) . . . . ? C19 C35 C36 C29 -0.5(3) . . . . ? C20 C23 C25 N3 -83.99(17) . . . . ? C20 C23 C25 C12 33.4(2) . . . . ? C20 C33 C41 C38 59.7(3) . . . . ? C21 N3 C25 C12 -145.10(16) . . . . ? C21 N3 C25 C23 -20.8(2) . . . . ? C21 N3 C32 C27 118.3(2) . . . . ? C21 C18 C23 C20 83.10(17) . . . . ? C21 C18 C23 C25 -36.60(17) . . . . ? C21 C18 C38 C41 -74.8(2) . . . . ? C22 C17 C24 C30 -52.4(2) . . . . ? C22 C34 C37 C30 52.4(2) . . . . ? C23 C18 C21 N3 25.75(19) . . . . ? C23 C18 C21 O0AA -155.00(19) . . . . ? C23 C18 C38 C41 45.0(3) . . . . ? C23 C20 C33 C41 -59.1(2) . . . . ? C24 C17 C22 C10 -80.38(16) . . . . ? C24 C17 C22 C34 45.7(2) . . . . ? C24 C30 C37 C34 -59.9(2) . . . . ? C25 N3 C21 O0AA 177.66(17) . . . . ? C25 N3 C21 C18 -3.1(2) . . . . ? C25 N3 C32 C27 -57.7(2) . . . . ? C25 C12 C15 C16 179.19(16) . . . . ? C25 C12 C15 C27 -2.9(3) . . . . ? C26 N C7 C11 -30.8(2) . . . . ? C26 N C7 C17 -153.93(15) . . . . ? C26 N C10 O -0.5(3) . . . . ? C26 N C10 C22 179.04(15) . . . . ? C27 C15 C16 C13 -177.50(19) . . . . ? C27 C15 C16 C40 2.5(4) . . . . ? C28 C4 C9 C14 -179.87(18) . . . . ? C28 C4 C9 C19 0.4(3) . . . . ? C28 C4 C11 N0AA -179.99(16) . . . . ? C28 C4 C11 C7 3.4(3) . . . . ? C31 C13 C16 C15 -179.43(18) . . . . ? C31 C13 C16 C40 0.6(3) . . . . ? C32 N3 C21 O0AA 1.3(3) . . . . ? C32 N3 C21 C18 -179.39(17) . . . . ? C32 N3 C25 C12 31.4(2) . . . . ? C32 N3 C25 C23 155.71(17) . . . . ? C33 C20 C23 C18 49.9(2) . . . . ? C33 C20 C23 C25 162.48(16) . . . . ? C38 C18 C21 N3 153.36(16) . . . . ? C38 C18 C21 O0AA -27.4(3) . . . . ? C38 C18 C23 C20 -43.8(2) . . . . ? C38 C18 C23 C25 -163.53(16) . . . . ? C40 C39 C42 C31 0.5(4) . . . . ? C42 C39 C40 C16 0.0(3) . . . . ? data_crr319 _database_code_depnum_ccdc_archive 'CCDC 876038' _audit_creation_method SHELXL-97 _chemical_name_systematic ; 13b-hydroxy-7,8,13,13b-tetrahydro-5H-benzo[1,2]indolizino[8,7-b]indol-5-one ; _chemical_name_common 13b-hydroxy-7,8,13,13b-tetrahydro-5H-benzo[1,2]indolizino[8,7-b]indol-5-one _chemical_melting_point 436 _chemical_formula_moiety 'C18 H14 N2 O2' _chemical_formula_sum 'C18 H14 N2 O2' _chemical_formula_weight 290.31 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' 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 7.6018(13) _cell_length_b 9.8711(16) _cell_length_c 10.1290(17) _cell_angle_alpha 99.173(2) _cell_angle_beta 106.817(2) _cell_angle_gamma 101.998(2) _cell_volume 691.8(2) _cell_formula_units_Z 2 _cell_measurement_temperature 298(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description block _exptl_crystal_colour colourless _exptl_crystal_size_max 0.41 _exptl_crystal_size_mid 0.38 _exptl_crystal_size_min 0.36 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.394 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 304 _exptl_absorpt_coefficient_mu 0.092 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.9631 _exptl_absorpt_correction_T_max 0.9675 _exptl_absorpt_process_details sadabs _exptl_special_details ; ? ; _diffrn_ambient_temperature 298(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'CCD area detector' _diffrn_measurement_method 'phi and omega scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 5255 _diffrn_reflns_av_R_equivalents 0.0177 _diffrn_reflns_av_sigmaI/netI 0.0236 _diffrn_reflns_limit_h_min -9 _diffrn_reflns_limit_h_max 9 _diffrn_reflns_limit_k_min -12 _diffrn_reflns_limit_k_max 12 _diffrn_reflns_limit_l_min -12 _diffrn_reflns_limit_l_max 12 _diffrn_reflns_theta_min 2.16 _diffrn_reflns_theta_max 25.83 _reflns_number_total 2631 _reflns_number_gt 2352 _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^)+(0.0525P)^2^+0.1723P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment mixed _refine_ls_extinction_method SHELXL _refine_ls_extinction_coef 0.060(6) _refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^ _refine_ls_number_reflns 2631 _refine_ls_number_parameters 205 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0463 _refine_ls_R_factor_gt 0.0420 _refine_ls_wR_factor_ref 0.1083 _refine_ls_wR_factor_gt 0.1053 _refine_ls_goodness_of_fit_ref 1.054 _refine_ls_restrained_S_all 1.054 _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 0.7530(2) 0.87862(17) 0.42168(17) 0.0455(4) Uani 1 1 d . . . H1 H 0.7154 0.9626 0.4232 0.055 Uiso 1 1 calc R . . C2 C 0.8540(3) 0.83916(19) 0.33461(18) 0.0536(4) Uani 1 1 d . . . H2 H 0.8864 0.8988 0.2780 0.064 Uiso 1 1 calc R . . C3 C 0.9075(3) 0.7139(2) 0.32989(19) 0.0533(4) Uani 1 1 d . . . H3 H 0.9731 0.6896 0.2691 0.064 Uiso 1 1 calc R . . C4 C 0.8650(2) 0.62428(18) 0.41403(17) 0.0465(4) Uani 1 1 d . . . H4 H 0.9013 0.5398 0.4115 0.056 Uiso 1 1 calc R . . C5 C 0.7667(2) 0.66397(15) 0.50231(15) 0.0368(3) Uani 1 1 d . . . C6 C 0.7103(2) 0.78857(15) 0.50601(15) 0.0359(3) Uani 1 1 d . . . C7 C 0.7090(2) 0.59231(14) 0.60620(15) 0.0358(3) Uani 1 1 d . . . C8 C 0.5963(2) 0.79787(14) 0.60638(15) 0.0348(3) Uani 1 1 d . . . C9 C 0.5645(2) 0.65694(16) 0.79047(17) 0.0447(4) Uani 1 1 d . . . H9A H 0.5823 0.5679 0.8133 0.054 Uiso 1 1 calc R . . H9B H 0.4313 0.6546 0.7727 0.054 Uiso 1 1 calc R . . C10 C 0.6887(3) 0.78031(16) 0.91516(17) 0.0460(4) Uani 1 1 d . . . H10A H 0.6331 0.7845 0.9901 0.055 Uiso 1 1 calc R . . H10B H 0.8147 0.7664 0.9524 0.055 Uiso 1 1 calc R . . C11 C 0.7038(2) 0.91665(16) 0.86680(16) 0.0383(3) Uani 1 1 d . . . C12 C 0.6659(2) 0.92360(14) 0.72914(15) 0.0346(3) Uani 1 1 d . . . C13 C 0.7381(2) 1.14801(15) 0.85110(16) 0.0374(3) Uani 1 1 d . . . C14 C 0.7731(2) 1.29537(16) 0.89407(18) 0.0466(4) Uani 1 1 d . . . H14 H 0.7607 1.3522 0.8288 0.056 Uiso 1 1 calc R . . C15 C 0.8267(3) 1.35287(18) 1.03722(19) 0.0526(4) Uani 1 1 d . . . H15 H 0.8527 1.4509 1.0695 0.063 Uiso 1 1 calc R . . C16 C 0.8430(3) 1.26803(19) 1.13483(18) 0.0525(4) Uani 1 1 d . . . H16 H 0.8808 1.3105 1.2310 0.063 Uiso 1 1 calc R . . C17 C 0.8047(3) 1.12316(18) 1.09233(17) 0.0496(4) Uani 1 1 d . . . H17 H 0.8132 1.0674 1.1585 0.060 Uiso 1 1 calc R . . C18 C 0.7524(2) 1.06020(16) 0.94771(16) 0.0387(4) Uani 1 1 d . . . N1 N 0.61325(18) 0.67180(12) 0.66372(13) 0.0369(3) Uani 1 1 d . . . N2 N 0.68596(19) 1.06259(13) 0.71722(14) 0.0387(3) Uani 1 1 d . . . O1 O 0.74218(16) 0.48272(10) 0.63777(12) 0.0455(3) Uani 1 1 d . . . O2 O 0.40270(15) 0.78929(11) 0.53135(11) 0.0421(3) Uani 1 1 d . . . H2B H 0.3508 0.7098 0.4786 0.063 Uiso 1 1 calc R . . H2A H 0.662(2) 1.0940(19) 0.6375(19) 0.051(5) Uiso 1 1 d . . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 C1 0.0575(10) 0.0391(8) 0.0433(9) 0.0142(7) 0.0167(8) 0.0168(7) C2 0.0650(11) 0.0557(10) 0.0460(9) 0.0175(8) 0.0248(9) 0.0157(9) C3 0.0591(11) 0.0595(11) 0.0480(10) 0.0090(8) 0.0268(8) 0.0201(9) C4 0.0518(9) 0.0428(9) 0.0452(9) 0.0046(7) 0.0149(7) 0.0199(7) C5 0.0391(8) 0.0335(7) 0.0335(7) 0.0044(6) 0.0063(6) 0.0118(6) C6 0.0389(8) 0.0326(7) 0.0324(7) 0.0046(6) 0.0070(6) 0.0104(6) C7 0.0377(8) 0.0270(7) 0.0358(8) 0.0036(6) 0.0038(6) 0.0089(6) C8 0.0389(8) 0.0295(7) 0.0365(8) 0.0096(6) 0.0101(6) 0.0127(6) C9 0.0579(10) 0.0344(8) 0.0483(9) 0.0154(7) 0.0239(8) 0.0129(7) C10 0.0633(10) 0.0407(8) 0.0405(9) 0.0164(7) 0.0202(8) 0.0187(8) C11 0.0447(8) 0.0351(8) 0.0371(8) 0.0100(6) 0.0135(6) 0.0137(6) C12 0.0405(8) 0.0295(7) 0.0373(8) 0.0099(6) 0.0138(6) 0.0143(6) C13 0.0403(8) 0.0345(7) 0.0380(8) 0.0059(6) 0.0146(6) 0.0113(6) C14 0.0590(10) 0.0334(8) 0.0508(9) 0.0069(7) 0.0247(8) 0.0128(7) C15 0.0590(10) 0.0366(8) 0.0585(11) -0.0033(8) 0.0247(9) 0.0088(7) C16 0.0542(10) 0.0535(10) 0.0411(9) -0.0058(8) 0.0138(8) 0.0119(8) C17 0.0592(10) 0.0518(10) 0.0375(8) 0.0091(7) 0.0145(8) 0.0175(8) C18 0.0410(8) 0.0372(8) 0.0376(8) 0.0067(6) 0.0127(6) 0.0118(6) N1 0.0463(7) 0.0288(6) 0.0390(7) 0.0108(5) 0.0153(6) 0.0136(5) N2 0.0530(8) 0.0308(6) 0.0346(7) 0.0096(5) 0.0146(6) 0.0148(6) O1 0.0577(7) 0.0296(5) 0.0474(6) 0.0096(5) 0.0104(5) 0.0178(5) O2 0.0419(6) 0.0342(6) 0.0452(6) 0.0044(5) 0.0067(5) 0.0146(5) _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 1.381(2) . ? C1 C2 1.388(2) . ? C1 H1 0.9300 . ? C2 C3 1.378(3) . ? C2 H2 0.9300 . ? C3 C4 1.376(2) . ? C3 H3 0.9300 . ? C4 C5 1.382(2) . ? C4 H4 0.9300 . ? C5 C6 1.383(2) . ? C5 C7 1.475(2) . ? C6 C8 1.519(2) . ? C7 O1 1.2301(17) . ? C7 N1 1.3499(19) . ? C8 O2 1.4253(17) . ? C8 N1 1.4685(17) . ? C8 C12 1.490(2) . ? C9 N1 1.4561(19) . ? C9 C10 1.520(2) . ? C9 H9A 0.9700 . ? C9 H9B 0.9700 . ? C10 C11 1.498(2) . ? C10 H10A 0.9700 . ? C10 H10B 0.9700 . ? C11 C12 1.356(2) . ? C11 C18 1.433(2) . ? C12 N2 1.3771(18) . ? C13 N2 1.3757(19) . ? C13 C14 1.395(2) . ? C13 C18 1.403(2) . ? C14 C15 1.375(2) . ? C14 H14 0.9300 . ? C15 C16 1.389(3) . ? C15 H15 0.9300 . ? C16 C17 1.369(2) . ? C16 H16 0.9300 . ? C17 C18 1.400(2) . ? C17 H17 0.9300 . ? N2 H2A 0.894(19) . ? O2 H2B 0.8200 . ? 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 117.50(15) . . ? C6 C1 H1 121.2 . . ? C2 C1 H1 121.2 . . ? C3 C2 C1 121.68(16) . . ? C3 C2 H2 119.2 . . ? C1 C2 H2 119.2 . . ? C4 C3 C2 120.77(16) . . ? C4 C3 H3 119.6 . . ? C2 C3 H3 119.6 . . ? C3 C4 C5 117.78(15) . . ? C3 C4 H4 121.1 . . ? C5 C4 H4 121.1 . . ? C4 C5 C6 121.68(14) . . ? C4 C5 C7 129.41(14) . . ? C6 C5 C7 108.90(13) . . ? C1 C6 C5 120.57(14) . . ? C1 C6 C8 130.25(13) . . ? C5 C6 C8 109.12(12) . . ? O1 C7 N1 125.55(14) . . ? O1 C7 C5 127.76(14) . . ? N1 C7 C5 106.68(12) . . ? O2 C8 N1 111.63(11) . . ? O2 C8 C12 107.15(11) . . ? N1 C8 C12 107.39(11) . . ? O2 C8 C6 110.98(11) . . ? N1 C8 C6 101.35(11) . . ? C12 C8 C6 118.23(12) . . ? N1 C9 C10 110.64(12) . . ? N1 C9 H9A 109.5 . . ? C10 C9 H9A 109.5 . . ? N1 C9 H9B 109.5 . . ? C10 C9 H9B 109.5 . . ? H9A C9 H9B 108.1 . . ? C11 C10 C9 109.27(13) . . ? C11 C10 H10A 109.8 . . ? C9 C10 H10A 109.8 . . ? C11 C10 H10B 109.8 . . ? C9 C10 H10B 109.8 . . ? H10A C10 H10B 108.3 . . ? C12 C11 C18 106.41(13) . . ? C12 C11 C10 123.86(14) . . ? C18 C11 C10 129.71(14) . . ? C11 C12 N2 110.58(13) . . ? C11 C12 C8 124.87(13) . . ? N2 C12 C8 124.37(13) . . ? N2 C13 C14 129.80(14) . . ? N2 C13 C18 107.87(13) . . ? C14 C13 C18 122.33(14) . . ? C15 C14 C13 117.04(16) . . ? C15 C14 H14 121.5 . . ? C13 C14 H14 121.5 . . ? C14 C15 C16 121.59(16) . . ? C14 C15 H15 119.2 . . ? C16 C15 H15 119.2 . . ? C17 C16 C15 121.33(16) . . ? C17 C16 H16 119.3 . . ? C15 C16 H16 119.3 . . ? C16 C17 C18 119.03(16) . . ? C16 C17 H17 120.5 . . ? C18 C17 H17 120.5 . . ? C17 C18 C13 118.67(14) . . ? C17 C18 C11 134.27(15) . . ? C13 C18 C11 107.06(13) . . ? C7 N1 C9 124.99(12) . . ? C7 N1 C8 113.73(12) . . ? C9 N1 C8 120.06(12) . . ? C13 N2 C12 108.06(12) . . ? C13 N2 H2A 124.3(11) . . ? C12 N2 H2A 127.5(11) . . ? C8 O2 H2B 109.5 . . ? _diffrn_measured_fraction_theta_max 0.985 _diffrn_reflns_theta_full 25.83 _diffrn_measured_fraction_theta_full 0.985 _refine_diff_density_max 0.184 _refine_diff_density_min -0.185 _refine_diff_density_rms 0.035