# Electronic Supplementary Material (ESI) for Organic & Biomolecular Chemistry # This journal is © The Royal Society of Chemistry 2014 ####################################################################### # # 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_3h _audit_creation_method SHELXL-97 _chemical_name_systematic ; 8-Acetyl-1-aza-7-phenylbicyclo[4.3.0]nona-2,4,6,8-tetraene ; _chemical_name_common ? _chemical_melting_point 142-144 _chemical_formula_moiety ? _chemical_formula_sum 'C16 H13 N O' _chemical_formula_weight 235.27 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Monoclinic _symmetry_space_group_name_H-M 'P2(1)/c ' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y-1/2, z-1/2' _cell_length_a 9.286(2) _cell_length_b 11.358(3) _cell_length_c 11.827(3) _cell_angle_alpha 90.00 _cell_angle_beta 98.495(4) _cell_angle_gamma 90.00 _cell_volume 1233.8(5) _cell_formula_units_Z 4 _cell_measurement_temperature 298(2) _cell_measurement_reflns_used 3566 _cell_measurement_theta_min 2.50 _cell_measurement_theta_max 25.64 _exptl_crystal_description block _exptl_crystal_colour brown _exptl_crystal_size_max 0.8 _exptl_crystal_size_mid 0.4 _exptl_crystal_size_min 0.2 _exptl_crystal_density_meas 1.267 _exptl_crystal_density_diffrn 1.267 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 496 _exptl_absorpt_coefficient_mu 0.079 _exptl_absorpt_correction_type none _exptl_absorpt_correction_T_min ? _exptl_absorpt_correction_T_max ? _exptl_absorpt_process_details ? _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 12115 _diffrn_reflns_av_R_equivalents 0.0325 _diffrn_reflns_av_sigmaI/netI 0.0227 _diffrn_reflns_limit_h_min -11 _diffrn_reflns_limit_h_max 11 _diffrn_reflns_limit_k_min -13 _diffrn_reflns_limit_k_max 13 _diffrn_reflns_limit_l_min -14 _diffrn_reflns_limit_l_max 14 _diffrn_reflns_theta_min 2.22 _diffrn_reflns_theta_max 25.89 _reflns_number_total 2380 _reflns_number_gt 2103 _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 'Bruker SHELXTL' _computing_publication_material 'Bruker SHELXTL' _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0453P)^2^+0.4428P] 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 2380 _refine_ls_number_parameters 164 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0637 _refine_ls_R_factor_gt 0.0552 _refine_ls_wR_factor_ref 0.1272 _refine_ls_wR_factor_gt 0.1225 _refine_ls_goodness_of_fit_ref 1.145 _refine_ls_restrained_S_all 1.145 _refine_ls_shift/su_max 0.001 _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 N1 N 0.87616(16) 1.10778(13) 0.43955(12) 0.0406(4) Uani 1 1 d . . . C5 C 0.77862(18) 1.01433(15) 0.44172(15) 0.0379(4) Uani 1 1 d . . . O1 O 0.91885(17) 0.85808(14) 0.14538(13) 0.0658(5) Uani 1 1 d . . . C6 C 0.79260(18) 0.94148(15) 0.35069(14) 0.0371(4) Uani 1 1 d . . . C7 C 0.90214(19) 0.99226(15) 0.29340(15) 0.0390(4) Uani 1 1 d . . . C11 C 0.69903(19) 0.83795(15) 0.32074(15) 0.0392(4) Uani 1 1 d . . . C9 C 0.9632(2) 0.94725(17) 0.19528(16) 0.0460(5) Uani 1 1 d . . . C3 C 0.6942(2) 1.10716(18) 0.60098(17) 0.0517(5) Uani 1 1 d . . . H3 H 0.6323 1.1089 0.6560 0.062 Uiso 1 1 calc R . . C8 C 0.9506(2) 1.09319(16) 0.35099(15) 0.0435(4) Uani 1 1 d . . . H8 H 1.0227 1.1431 0.3320 0.052 Uiso 1 1 calc R . . C12 C 0.6804(2) 0.75328(16) 0.40116(17) 0.0473(5) Uani 1 1 d . . . H12 H 0.7331 0.7584 0.4742 0.057 Uiso 1 1 calc R . . C4 C 0.6877(2) 1.01669(17) 0.52720(16) 0.0442(5) Uani 1 1 d . . . H4 H 0.6229 0.9553 0.5326 0.053 Uiso 1 1 calc R . . C16 C 0.6188(2) 0.82701(17) 0.21260(16) 0.0481(5) Uani 1 1 d . . . H16 H 0.6300 0.8825 0.1568 0.058 Uiso 1 1 calc R . . C1 C 0.8839(2) 1.19886(17) 0.51710(18) 0.0510(5) Uani 1 1 d . . . H1 H 0.9509 1.2593 0.5148 0.061 Uiso 1 1 calc R . . C2 C 0.7947(2) 1.19959(19) 0.59533(18) 0.0548(5) Uani 1 1 d . . . H2 H 0.7985 1.2617 0.6469 0.066 Uiso 1 1 calc R . . C14 C 0.5059(3) 0.6525(2) 0.2675(2) 0.0640(6) Uani 1 1 d . . . H14 H 0.4410 0.5905 0.2499 0.077 Uiso 1 1 calc R . . C13 C 0.5847(2) 0.66135(18) 0.3744(2) 0.0598(6) Uani 1 1 d . . . H13 H 0.5736 0.6049 0.4294 0.072 Uiso 1 1 calc R . . C15 C 0.5230(2) 0.7352(2) 0.18679(19) 0.0604(6) Uani 1 1 d . . . H15 H 0.4696 0.7295 0.1140 0.072 Uiso 1 1 calc R . . C10 C 1.0861(3) 1.0135(2) 0.15646(19) 0.0646(6) Uani 1 1 d . . . H10A H 1.1327 0.9647 0.1063 0.097 Uiso 1 1 calc R . . H10B H 1.1555 1.0350 0.2216 0.097 Uiso 1 1 calc R . . H10C H 1.0492 1.0833 0.1165 0.097 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 0.0427(8) 0.0360(8) 0.0412(8) -0.0027(6) 0.0005(7) -0.0009(6) C5 0.0350(9) 0.0362(9) 0.0407(9) 0.0006(7) -0.0006(7) 0.0015(7) O1 0.0745(10) 0.0597(9) 0.0683(10) -0.0197(8) 0.0276(8) -0.0049(8) C6 0.0367(9) 0.0340(9) 0.0393(9) 0.0011(7) 0.0017(7) 0.0035(7) C7 0.0427(10) 0.0358(9) 0.0375(9) 0.0039(7) 0.0024(8) 0.0032(8) C11 0.0389(9) 0.0367(9) 0.0425(10) -0.0055(8) 0.0078(8) 0.0037(7) C9 0.0509(11) 0.0454(11) 0.0411(10) 0.0050(9) 0.0051(8) 0.0052(9) C3 0.0467(11) 0.0610(13) 0.0482(11) -0.0093(10) 0.0096(9) 0.0066(10) C8 0.0448(10) 0.0406(10) 0.0451(10) 0.0046(8) 0.0067(8) -0.0034(8) C12 0.0507(11) 0.0427(11) 0.0485(11) 0.0000(9) 0.0070(9) 0.0003(9) C4 0.0383(10) 0.0461(11) 0.0478(11) -0.0014(8) 0.0046(8) 0.0025(8) C16 0.0536(11) 0.0477(11) 0.0427(10) -0.0068(9) 0.0062(9) -0.0021(9) C1 0.0544(12) 0.0411(10) 0.0552(12) -0.0102(9) 0.0007(10) -0.0028(9) C2 0.0583(13) 0.0525(12) 0.0515(12) -0.0170(10) 0.0006(10) 0.0053(10) C14 0.0632(14) 0.0528(13) 0.0781(16) -0.0239(12) 0.0175(12) -0.0205(11) C13 0.0691(14) 0.0438(11) 0.0699(15) -0.0009(10) 0.0219(12) -0.0095(10) C15 0.0600(13) 0.0653(14) 0.0545(13) -0.0226(11) 0.0038(10) -0.0096(11) C10 0.0682(15) 0.0778(16) 0.0512(12) 0.0065(11) 0.0199(11) -0.0081(12) _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 1.348(2) . ? N1 C1 1.377(2) . ? N1 C5 1.398(2) . ? C5 C6 1.379(2) . ? C5 C4 1.410(3) . ? O1 C9 1.213(2) . ? C6 C7 1.425(2) . ? C6 C11 1.474(2) . ? C7 C8 1.375(2) . ? C7 C9 1.458(3) . ? C11 C12 1.381(3) . ? C11 C16 1.387(3) . ? C9 C10 1.495(3) . ? C3 C4 1.344(3) . ? C3 C2 1.412(3) . ? C12 C13 1.377(3) . ? C16 C15 1.375(3) . ? C1 C2 1.330(3) . ? C14 C15 1.365(3) . ? C14 C13 1.368(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 C8 N1 C1 128.88(17) . . ? C8 N1 C5 109.20(15) . . ? C1 N1 C5 121.88(16) . . ? C6 C5 N1 107.77(15) . . ? C6 C5 C4 134.96(17) . . ? N1 C5 C4 117.19(16) . . ? C5 C6 C7 106.53(15) . . ? C5 C6 C11 123.11(16) . . ? C7 C6 C11 130.21(16) . . ? C8 C7 C6 107.84(16) . . ? C8 C7 C9 123.33(17) . . ? C6 C7 C9 128.75(16) . . ? C12 C11 C16 117.89(17) . . ? C12 C11 C6 121.28(16) . . ? C16 C11 C6 120.68(16) . . ? O1 C9 C7 122.40(18) . . ? O1 C9 C10 119.38(18) . . ? C7 C9 C10 118.22(18) . . ? C4 C3 C2 120.28(19) . . ? N1 C8 C7 108.65(16) . . ? C13 C12 C11 120.77(19) . . ? C3 C4 C5 120.41(18) . . ? C15 C16 C11 120.9(2) . . ? C2 C1 N1 119.43(19) . . ? C1 C2 C3 120.79(18) . . ? C15 C14 C13 119.6(2) . . ? C14 C13 C12 120.5(2) . . ? C14 C15 C16 120.3(2) . . ? _diffrn_measured_fraction_theta_max 0.996 _diffrn_reflns_theta_full 25.89 _diffrn_measured_fraction_theta_full 0.996 _refine_diff_density_max 0.197 _refine_diff_density_min -0.152 _refine_diff_density_rms 0.034 _database_code_depnum_ccdc_archive 'CCDC 950387' ####################################################################### # # 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_4h _audit_creation_method SHELXL-97 _chemical_name_systematic ; 8-Acetyl-1-aza-9-(3-oxobutyl)-7-phenylbicyclo[4.3.0]nona-2,4,6,8-tetraene ; _chemical_name_common ? _chemical_melting_point 122-123 _chemical_formula_moiety ? _chemical_formula_sum 'C20 H19 N O2' _chemical_formula_weight 305.36 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 9.1844(10) _cell_length_b 9.6681(11) _cell_length_c 10.4799(12) _cell_angle_alpha 81.098(2) _cell_angle_beta 65.775(2) _cell_angle_gamma 79.753(2) _cell_volume 831.62(16) _cell_formula_units_Z 2 _cell_measurement_temperature 273(2) _cell_measurement_reflns_used 3146 _cell_measurement_theta_min 2.45 _cell_measurement_theta_max 25.81 _exptl_crystal_description block _exptl_crystal_colour colorless _exptl_crystal_size_max 0.6 _exptl_crystal_size_mid 0.4 _exptl_crystal_size_min 0.2 _exptl_crystal_density_meas 1.219 _exptl_crystal_density_diffrn 1.219 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 324 _exptl_absorpt_coefficient_mu 0.079 _exptl_absorpt_correction_type none _exptl_absorpt_correction_T_min ? _exptl_absorpt_correction_T_max ? _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 273(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 8707 _diffrn_reflns_av_R_equivalents 0.0346 _diffrn_reflns_av_sigmaI/netI 0.0357 _diffrn_reflns_limit_h_min -11 _diffrn_reflns_limit_h_max 11 _diffrn_reflns_limit_k_min -11 _diffrn_reflns_limit_k_max 11 _diffrn_reflns_limit_l_min -12 _diffrn_reflns_limit_l_max 12 _diffrn_reflns_theta_min 2.14 _diffrn_reflns_theta_max 26.04 _reflns_number_total 3258 _reflns_number_gt 3107 _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 'Bruker SHELXTL' _computing_publication_material 'Bruker SHELXTL' _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0582P)^2^+0.5349P] 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 3258 _refine_ls_number_parameters 210 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0932 _refine_ls_R_factor_gt 0.0887 _refine_ls_wR_factor_ref 0.1889 _refine_ls_wR_factor_gt 0.1860 _refine_ls_goodness_of_fit_ref 1.264 _refine_ls_restrained_S_all 1.264 _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 N1 N 0.4120(2) 0.1773(2) 0.6606(2) 0.0406(5) Uani 1 1 d . . . O2 O -0.1440(2) 0.0294(2) 0.9348(2) 0.0574(6) Uani 1 1 d . . . C13 C -0.0482(3) -0.0443(3) 0.8477(3) 0.0423(6) Uani 1 1 d . . . C15 C 0.5773(3) 0.3482(3) 0.3018(3) 0.0402(6) Uani 1 1 d . . . O1 O 0.0760(3) 0.2537(3) 0.4749(3) 0.0728(7) Uani 1 1 d . . . C7 C 0.3139(3) 0.2662(3) 0.5003(3) 0.0406(6) Uani 1 1 d . . . C8 C 0.2761(3) 0.1985(3) 0.6343(3) 0.0400(6) Uani 1 1 d . . . C5 C 0.5384(3) 0.2319(3) 0.5441(3) 0.0403(6) Uani 1 1 d . . . C12 C 0.1025(3) 0.0047(3) 0.7372(3) 0.0462(7) Uani 1 1 d . . . H12A H 0.1048 -0.0055 0.6457 0.055 Uiso 1 1 calc R . . H12B H 0.1940 -0.0562 0.7471 0.055 Uiso 1 1 calc R . . C11 C 0.1207(3) 0.1559(3) 0.7421(3) 0.0422(6) Uani 1 1 d . . . H11A H 0.0324 0.2177 0.7272 0.051 Uiso 1 1 calc R . . H11B H 0.1141 0.1676 0.8346 0.051 Uiso 1 1 calc R . . C4 C 0.6892(3) 0.2195(3) 0.5528(3) 0.0484(7) Uani 1 1 d . . . H4 H 0.7757 0.2534 0.4769 0.058 Uiso 1 1 calc R . . C6 C 0.4786(3) 0.2878(3) 0.4433(3) 0.0396(6) Uani 1 1 d . . . C16 C 0.6652(4) 0.4572(3) 0.2846(3) 0.0517(7) Uani 1 1 d . . . H16 H 0.6604 0.4942 0.3633 0.062 Uiso 1 1 calc R . . C1 C 0.4349(4) 0.1143(3) 0.7797(3) 0.0513(7) Uani 1 1 d . . . H1 H 0.3502 0.0782 0.8559 0.062 Uiso 1 1 calc R . . C20 C 0.5874(4) 0.2960(3) 0.1824(3) 0.0543(8) Uani 1 1 d . . . H20 H 0.5301 0.2225 0.1910 0.065 Uiso 1 1 calc R . . C9 C 0.1920(3) 0.3152(3) 0.4408(3) 0.0492(7) Uani 1 1 d . . . C18 C 0.7677(5) 0.4592(4) 0.0360(3) 0.0716(10) Uani 1 1 d . . . H18 H 0.8313 0.4966 -0.0529 0.086 Uiso 1 1 calc R . . C2 C 0.5786(4) 0.1055(4) 0.7851(3) 0.0622(9) Uani 1 1 d . . . H2 H 0.5935 0.0636 0.8657 0.075 Uiso 1 1 calc R . . C17 C 0.7596(4) 0.5112(4) 0.1528(4) 0.0658(9) Uani 1 1 d . . . H17 H 0.8185 0.5838 0.1431 0.079 Uiso 1 1 calc R . . C19 C 0.6819(5) 0.3519(4) 0.0503(3) 0.0701(10) Uani 1 1 d . . . H19 H 0.6871 0.3162 -0.0292 0.084 Uiso 1 1 calc R . . C3 C 0.7091(4) 0.1592(4) 0.6697(4) 0.0613(9) Uani 1 1 d . . . H3 H 0.8088 0.1527 0.6749 0.074 Uiso 1 1 calc R . . C14 C -0.0737(5) -0.1910(4) 0.8438(4) 0.0760(11) Uani 1 1 d . . . H14A H -0.1758 -0.2103 0.9159 0.114 Uiso 1 1 calc R . . H14B H 0.0107 -0.2562 0.8592 0.114 Uiso 1 1 calc R . . H14C H -0.0725 -0.2012 0.7537 0.114 Uiso 1 1 calc R . . C10 C 0.2068(4) 0.4477(4) 0.3437(4) 0.0715(10) Uani 1 1 d . . . H10A H 0.1082 0.4767 0.3302 0.107 Uiso 1 1 calc R . . H10B H 0.2935 0.4306 0.2548 0.107 Uiso 1 1 calc R . . H10C H 0.2282 0.5207 0.3837 0.107 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 0.0349(11) 0.0479(13) 0.0364(11) 0.0035(9) -0.0118(9) -0.0111(9) O2 0.0472(12) 0.0597(13) 0.0502(12) -0.0019(10) -0.0019(10) -0.0148(10) C13 0.0436(15) 0.0476(15) 0.0372(14) 0.0079(12) -0.0189(12) -0.0126(12) C15 0.0408(14) 0.0385(14) 0.0366(13) -0.0029(11) -0.0109(11) -0.0045(11) O1 0.0531(13) 0.1018(19) 0.0733(16) 0.0120(13) -0.0346(12) -0.0275(13) C7 0.0403(14) 0.0419(14) 0.0395(14) -0.0024(11) -0.0143(11) -0.0096(11) C8 0.0374(13) 0.0456(14) 0.0364(13) -0.0013(11) -0.0126(11) -0.0109(11) C5 0.0369(13) 0.0434(14) 0.0352(13) -0.0005(11) -0.0074(11) -0.0113(11) C12 0.0394(14) 0.0489(16) 0.0457(15) -0.0037(12) -0.0115(12) -0.0080(12) C11 0.0367(14) 0.0489(15) 0.0377(14) 0.0006(11) -0.0106(11) -0.0113(11) C4 0.0358(14) 0.0594(17) 0.0460(16) 0.0003(13) -0.0107(12) -0.0145(12) C6 0.0392(14) 0.0415(14) 0.0366(13) -0.0045(11) -0.0108(11) -0.0108(11) C16 0.0550(17) 0.0498(16) 0.0427(15) -0.0051(12) -0.0081(13) -0.0146(13) C1 0.0469(16) 0.0620(18) 0.0390(15) 0.0107(13) -0.0125(12) -0.0167(14) C20 0.0638(19) 0.0509(17) 0.0461(16) -0.0034(13) -0.0171(14) -0.0144(14) C9 0.0420(16) 0.0600(18) 0.0430(15) -0.0027(13) -0.0146(12) -0.0070(13) C18 0.082(2) 0.071(2) 0.0398(17) 0.0104(16) -0.0025(16) -0.0199(19) C2 0.0535(18) 0.085(2) 0.0521(18) 0.0198(16) -0.0300(15) -0.0182(16) C17 0.070(2) 0.0571(19) 0.057(2) 0.0061(15) -0.0079(16) -0.0268(16) C19 0.090(3) 0.073(2) 0.0367(16) -0.0052(15) -0.0132(16) -0.012(2) C3 0.0433(16) 0.079(2) 0.067(2) 0.0089(17) -0.0285(15) -0.0156(15) C14 0.085(3) 0.063(2) 0.068(2) -0.0012(17) -0.0102(19) -0.0331(19) C10 0.071(2) 0.075(2) 0.073(2) 0.0153(18) -0.0400(19) -0.0081(18) _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 1.359(3) . ? N1 C1 1.381(3) . ? N1 C5 1.404(3) . ? O2 C13 1.198(3) . ? C13 C14 1.487(4) . ? C13 C12 1.493(4) . ? C15 C20 1.383(4) . ? C15 C16 1.385(4) . ? C15 C6 1.476(3) . ? O1 C9 1.210(4) . ? C7 C8 1.385(4) . ? C7 C6 1.421(4) . ? C7 C9 1.469(4) . ? C8 C11 1.492(3) . ? C5 C6 1.380(4) . ? C5 C4 1.409(4) . ? C12 C11 1.511(4) . ? C4 C3 1.340(4) . ? C16 C17 1.374(4) . ? C1 C2 1.332(4) . ? C20 C19 1.382(4) . ? C9 C10 1.496(4) . ? C18 C17 1.363(5) . ? C18 C19 1.366(5) . ? C2 C3 1.417(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 C8 N1 C1 129.2(2) . . ? C8 N1 C5 109.8(2) . . ? C1 N1 C5 121.1(2) . . ? O2 C13 C14 121.4(3) . . ? O2 C13 C12 122.5(3) . . ? C14 C13 C12 116.2(3) . . ? C20 C15 C16 117.9(3) . . ? C20 C15 C6 121.1(2) . . ? C16 C15 C6 121.0(2) . . ? C8 C7 C6 108.5(2) . . ? C8 C7 C9 122.3(2) . . ? C6 C7 C9 128.9(2) . . ? N1 C8 C7 107.4(2) . . ? N1 C8 C11 121.5(2) . . ? C7 C8 C11 131.0(2) . . ? C6 C5 N1 107.5(2) . . ? C6 C5 C4 134.9(2) . . ? N1 C5 C4 117.7(2) . . ? C13 C12 C11 114.4(2) . . ? C8 C11 C12 112.6(2) . . ? C3 C4 C5 120.5(3) . . ? C5 C6 C7 106.8(2) . . ? C5 C6 C15 123.9(2) . . ? C7 C6 C15 129.1(2) . . ? C17 C16 C15 120.8(3) . . ? C2 C1 N1 119.8(3) . . ? C19 C20 C15 120.7(3) . . ? O1 C9 C7 120.7(3) . . ? O1 C9 C10 119.7(3) . . ? C7 C9 C10 119.5(3) . . ? C17 C18 C19 119.7(3) . . ? C1 C2 C3 120.8(3) . . ? C18 C17 C16 120.6(3) . . ? C18 C19 C20 120.3(3) . . ? C4 C3 C2 120.2(3) . . ? _diffrn_measured_fraction_theta_max 0.993 _diffrn_reflns_theta_full 26.04 _diffrn_measured_fraction_theta_full 0.993 _refine_diff_density_max 0.263 _refine_diff_density_min -0.381 _refine_diff_density_rms 0.088 _database_code_depnum_ccdc_archive 'CCDC 950388' ####################################################################### # # 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_9 _audit_creation_method SHELXL-97 _chemical_name_systematic ; 2-Aza-14-oxo-12-phenyltetracyclo[11.4.0.02,11.05,10]heptadeca-1(13),3,5(10),6,8,11-hexaene ; _chemical_name_common ? _chemical_melting_point 249-251 _chemical_formula_moiety 'C22 H17 N O' _chemical_formula_sum 'C22 H17 N O' _chemical_formula_weight 311.37 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Monoclinic _symmetry_space_group_name_H-M 'P2(1)/c ' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y-1/2, z-1/2' _cell_length_a 10.5099(15) _cell_length_b 17.731(3) _cell_length_c 9.3383(13) _cell_angle_alpha 90.00 _cell_angle_beta 115.207(2) _cell_angle_gamma 90.00 _cell_volume 1574.5(4) _cell_formula_units_Z 4 _cell_measurement_temperature 273(2) _cell_measurement_reflns_used 2828 _cell_measurement_theta_min 2.30 _cell_measurement_theta_max 21.66 _exptl_crystal_description block _exptl_crystal_colour pink _exptl_crystal_size_max 0.2 _exptl_crystal_size_mid 0.18 _exptl_crystal_size_min 0.16 _exptl_crystal_density_meas 1.314 _exptl_crystal_density_diffrn 1.314 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 656 _exptl_absorpt_coefficient_mu 0.080 _exptl_absorpt_correction_type none _exptl_absorpt_correction_T_min ? _exptl_absorpt_correction_T_max ? _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 273(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 15907 _diffrn_reflns_av_R_equivalents 0.0384 _diffrn_reflns_av_sigmaI/netI 0.0308 _diffrn_reflns_limit_h_min -12 _diffrn_reflns_limit_h_max 12 _diffrn_reflns_limit_k_min -21 _diffrn_reflns_limit_k_max 21 _diffrn_reflns_limit_l_min -11 _diffrn_reflns_limit_l_max 11 _diffrn_reflns_theta_min 2.14 _diffrn_reflns_theta_max 25.86 _reflns_number_total 3046 _reflns_number_gt 2114 _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 'Bruker SHELXTL' _computing_publication_material 'Bruker SHELXTL' _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0525P)^2^+0.2304P] 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 3046 _refine_ls_number_parameters 217 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0705 _refine_ls_R_factor_gt 0.0434 _refine_ls_wR_factor_ref 0.1143 _refine_ls_wR_factor_gt 0.1014 _refine_ls_goodness_of_fit_ref 1.010 _refine_ls_restrained_S_all 1.010 _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 N1 N 0.91450(13) 0.08973(8) 0.56613(16) 0.0479(4) Uani 1 1 d . . . O1 O 0.45914(13) 0.09404(8) 0.50528(16) 0.0687(4) Uani 1 1 d . . . C12 C 0.69583(16) 0.09206(9) 0.54065(19) 0.0480(4) Uani 1 1 d . . . C9 C 0.90102(16) 0.14208(9) 0.3185(2) 0.0467(4) Uani 1 1 d . . . C4 C 1.04771(17) 0.13086(10) 0.3767(2) 0.0517(4) Uani 1 1 d . . . C11 C 0.69327(16) 0.11733(9) 0.39485(19) 0.0451(4) Uani 1 1 d . . . C10 C 0.83051(16) 0.11689(9) 0.41261(19) 0.0451(4) Uani 1 1 d . . . C3 C 1.12250(17) 0.09597(10) 0.5288(2) 0.0589(5) Uani 1 1 d . . . H3 H 1.2180 0.0859 0.5644 0.071 Uiso 1 1 calc R . . C1 C 0.83249(17) 0.07512(10) 0.6431(2) 0.0498(4) Uani 1 1 d . . . C2 C 1.05857(17) 0.07776(10) 0.6195(2) 0.0563(5) Uani 1 1 d . . . H2 H 1.1100 0.0569 0.7191 0.068 Uiso 1 1 calc R . . C17 C 0.56752(15) 0.14077(9) 0.25218(19) 0.0447(4) Uani 1 1 d . . . C18 C 0.52216(17) 0.09918(10) 0.1136(2) 0.0547(5) Uani 1 1 d . . . H18 H 0.5709 0.0559 0.1107 0.066 Uiso 1 1 calc R . . C13 C 0.58334(18) 0.08471(10) 0.5915(2) 0.0540(5) Uani 1 1 d . . . C8 C 0.83145(19) 0.18026(10) 0.1749(2) 0.0576(5) Uani 1 1 d . . . H8 H 0.7353 0.1890 0.1363 0.069 Uiso 1 1 calc R . . C22 C 0.49412(18) 0.20545(10) 0.2522(2) 0.0562(5) Uani 1 1 d . . . H22 H 0.5226 0.2343 0.3438 0.067 Uiso 1 1 calc R . . C5 C 1.11686(19) 0.15617(11) 0.2863(2) 0.0626(5) Uani 1 1 d . . . H5 H 1.2131 0.1482 0.3231 0.075 Uiso 1 1 calc R . . C16 C 0.88333(19) 0.04527(12) 0.8070(2) 0.0633(5) Uani 1 1 d . . . H16A H 0.9315 0.0848 0.8825 0.076 Uiso 1 1 calc R . . H16B H 0.9493 0.0044 0.8224 0.076 Uiso 1 1 calc R . . C20 C 0.33443(18) 0.18538(12) -0.0177(2) 0.0633(5) Uani 1 1 d . . . H20 H 0.2561 0.2003 -0.1077 0.076 Uiso 1 1 calc R . . C19 C 0.40596(18) 0.12098(12) -0.0198(2) 0.0626(5) Uani 1 1 d . . . H19 H 0.3760 0.0920 -0.1115 0.075 Uiso 1 1 calc R . . C6 C 1.0458(2) 0.19230(12) 0.1455(3) 0.0681(6) Uani 1 1 d . . . H6 H 1.0933 0.2084 0.0867 0.082 Uiso 1 1 calc R . . C7 C 0.9021(2) 0.20492(11) 0.0902(2) 0.0650(5) Uani 1 1 d . . . H7 H 0.8538 0.2303 -0.0049 0.078 Uiso 1 1 calc R . . C21 C 0.37905(19) 0.22745(11) 0.1178(2) 0.0642(5) Uani 1 1 d . . . H21 H 0.3312 0.2714 0.1191 0.077 Uiso 1 1 calc R . . C14 C 0.6314(2) 0.06674(14) 0.7644(2) 0.0757(6) Uani 1 1 d . . . H14A H 0.6518 0.1137 0.8234 0.091 Uiso 1 1 calc R . . H14B H 0.5548 0.0423 0.7783 0.091 Uiso 1 1 calc R . . C15 C 0.7591(2) 0.01686(14) 0.8338(2) 0.0791(7) Uani 1 1 d . . . H15A H 0.7340 -0.0331 0.7879 0.095 Uiso 1 1 calc R . . H15B H 0.7873 0.0122 0.9467 0.095 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 0.0317(7) 0.0543(9) 0.0479(8) -0.0040(6) 0.0075(6) 0.0032(6) O1 0.0437(7) 0.0901(10) 0.0717(9) 0.0114(7) 0.0240(7) 0.0077(6) C12 0.0388(9) 0.0540(10) 0.0458(10) -0.0030(8) 0.0128(7) 0.0021(7) C9 0.0361(9) 0.0458(9) 0.0538(10) -0.0063(8) 0.0150(8) -0.0024(7) C4 0.0373(9) 0.0499(10) 0.0647(12) -0.0144(8) 0.0186(9) -0.0046(7) C11 0.0344(8) 0.0473(9) 0.0483(10) -0.0013(7) 0.0125(7) 0.0020(7) C10 0.0362(8) 0.0451(9) 0.0472(10) -0.0030(8) 0.0113(7) 0.0021(7) C3 0.0310(9) 0.0633(12) 0.0706(13) -0.0105(10) 0.0104(9) 0.0016(8) C1 0.0429(9) 0.0555(11) 0.0446(10) -0.0050(8) 0.0126(8) 0.0021(8) C2 0.0339(9) 0.0626(12) 0.0574(11) -0.0055(9) 0.0050(8) 0.0034(8) C17 0.0327(8) 0.0514(10) 0.0492(10) 0.0052(8) 0.0166(7) 0.0022(7) C18 0.0427(10) 0.0605(11) 0.0544(11) 0.0001(9) 0.0144(8) 0.0085(8) C13 0.0461(10) 0.0588(11) 0.0550(11) -0.0006(9) 0.0196(9) 0.0053(8) C8 0.0436(10) 0.0604(12) 0.0693(12) 0.0035(9) 0.0246(9) -0.0005(8) C22 0.0473(10) 0.0594(11) 0.0575(11) 0.0005(9) 0.0181(8) 0.0070(8) C5 0.0432(10) 0.0656(13) 0.0809(14) -0.0168(11) 0.0283(10) -0.0090(9) C16 0.0565(11) 0.0765(13) 0.0457(10) -0.0013(9) 0.0110(8) 0.0075(10) C20 0.0426(10) 0.0834(14) 0.0561(12) 0.0203(10) 0.0135(9) 0.0101(10) C19 0.0485(11) 0.0794(14) 0.0511(11) 0.0002(10) 0.0126(9) 0.0032(10) C6 0.0589(12) 0.0744(14) 0.0809(15) -0.0091(11) 0.0394(11) -0.0175(10) C7 0.0597(12) 0.0659(13) 0.0717(13) 0.0047(10) 0.0302(10) -0.0060(9) C21 0.0527(11) 0.0625(12) 0.0754(14) 0.0162(11) 0.0255(10) 0.0208(9) C14 0.0677(13) 0.1045(18) 0.0601(13) 0.0058(11) 0.0321(11) 0.0086(12) C15 0.0702(13) 0.1083(18) 0.0570(12) 0.0187(12) 0.0253(10) 0.0130(12) _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 C1 1.362(2) . ? N1 C2 1.394(2) . ? N1 C10 1.410(2) . ? O1 C13 1.218(2) . ? C12 C1 1.378(2) . ? C12 C11 1.423(2) . ? C12 C13 1.456(2) . ? C9 C8 1.398(2) . ? C9 C4 1.414(2) . ? C9 C10 1.441(2) . ? C4 C5 1.401(2) . ? C4 C3 1.438(3) . ? C11 C10 1.380(2) . ? C11 C17 1.481(2) . ? C3 C2 1.326(3) . ? C1 C16 1.487(2) . ? C17 C22 1.382(2) . ? C17 C18 1.386(2) . ? C18 C19 1.378(2) . ? C13 C14 1.506(3) . ? C8 C7 1.367(2) . ? C22 C21 1.378(2) . ? C5 C6 1.364(3) . ? C16 C15 1.516(3) . ? C20 C21 1.368(3) . ? C20 C19 1.372(3) . ? C6 C7 1.390(3) . ? C14 C15 1.504(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 C1 N1 C2 128.14(15) . . ? C1 N1 C10 109.80(13) . . ? C2 N1 C10 121.99(15) . . ? C1 C12 C11 108.81(15) . . ? C1 C12 C13 120.35(16) . . ? C11 C12 C13 130.81(15) . . ? C8 C9 C4 118.42(16) . . ? C8 C9 C10 122.69(14) . . ? C4 C9 C10 118.83(15) . . ? C5 C4 C9 118.95(17) . . ? C5 C4 C3 121.81(16) . . ? C9 C4 C3 119.21(17) . . ? C10 C11 C12 106.88(14) . . ? C10 C11 C17 126.60(15) . . ? C12 C11 C17 126.51(14) . . ? C11 C10 N1 107.09(14) . . ? C11 C10 C9 135.05(15) . . ? N1 C10 C9 117.65(14) . . ? C2 C3 C4 121.57(16) . . ? N1 C1 C12 107.39(15) . . ? N1 C1 C16 125.46(15) . . ? C12 C1 C16 127.14(16) . . ? C3 C2 N1 120.21(17) . . ? C22 C17 C18 118.15(15) . . ? C22 C17 C11 121.10(15) . . ? C18 C17 C11 120.73(15) . . ? C19 C18 C17 121.02(17) . . ? O1 C13 C12 124.23(17) . . ? O1 C13 C14 120.87(17) . . ? C12 C13 C14 114.87(15) . . ? C7 C8 C9 121.22(17) . . ? C21 C22 C17 120.52(18) . . ? C6 C5 C4 121.31(17) . . ? C1 C16 C15 109.32(15) . . ? C21 C20 C19 119.56(17) . . ? C20 C19 C18 120.02(18) . . ? C5 C6 C7 119.69(19) . . ? C8 C7 C6 120.4(2) . . ? C20 C21 C22 120.70(18) . . ? C15 C14 C13 114.60(17) . . ? C14 C15 C16 113.99(18) . . ? _diffrn_measured_fraction_theta_max 0.999 _diffrn_reflns_theta_full 25.86 _diffrn_measured_fraction_theta_full 0.999 _refine_diff_density_max 0.135 _refine_diff_density_min -0.148 _refine_diff_density_rms 0.030 _database_code_depnum_ccdc_archive 'CCDC 950389' ####################################################################### # # 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_3f _audit_creation_method SHELXL-97 _chemical_name_systematic ; 8-Acetyl-1-aza-2-Methoxy-7-methylbicyclo[4.3.0]nona-2,4,6,8-tetraene ; _chemical_name_common ? _chemical_melting_point 126-127 _chemical_formula_moiety ? _chemical_formula_sum 'C12 H13 N O2' _chemical_formula_weight 203.23 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 'Pbca ' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, -y, z+1/2' '-x, y+1/2, -z+1/2' 'x+1/2, -y+1/2, -z' '-x, -y, -z' 'x-1/2, y, -z-1/2' 'x, -y-1/2, z-1/2' '-x-1/2, y-1/2, z' _cell_length_a 14.886(4) _cell_length_b 8.048(2) _cell_length_c 17.590(4) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 2107.2(9) _cell_formula_units_Z 8 _cell_measurement_temperature 298(2) _cell_measurement_reflns_used 3213 _cell_measurement_theta_min 2.32 _cell_measurement_theta_max 21.37 _exptl_crystal_description block _exptl_crystal_colour brown _exptl_crystal_size_max 0.24 _exptl_crystal_size_mid 0.16 _exptl_crystal_size_min 0.14 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.281 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 864 _exptl_absorpt_coefficient_mu 0.088 _exptl_absorpt_correction_type none _exptl_absorpt_correction_T_min ? _exptl_absorpt_correction_T_max ? _exptl_absorpt_process_details ? _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 20200 _diffrn_reflns_av_R_equivalents 0.0415 _diffrn_reflns_av_sigmaI/netI 0.0217 _diffrn_reflns_limit_h_min -18 _diffrn_reflns_limit_h_max 18 _diffrn_reflns_limit_k_min -9 _diffrn_reflns_limit_k_max 9 _diffrn_reflns_limit_l_min -21 _diffrn_reflns_limit_l_max 21 _diffrn_reflns_theta_min 2.32 _diffrn_reflns_theta_max 26.03 _reflns_number_total 2070 _reflns_number_gt 1687 _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 'Bruker SHELXTL' _computing_publication_material 'Bruker SHELXTL' _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0561P)^2^+0.6009P] 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 2070 _refine_ls_number_parameters 139 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0792 _refine_ls_R_factor_gt 0.0635 _refine_ls_wR_factor_ref 0.1466 _refine_ls_wR_factor_gt 0.1385 _refine_ls_goodness_of_fit_ref 1.170 _refine_ls_restrained_S_all 1.170 _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 N1 N 0.26591(10) 0.19067(19) 0.34133(8) 0.0437(4) Uani 1 1 d . . . C5 C 0.36035(13) 0.1924(2) 0.33749(12) 0.0479(5) Uani 1 1 d . . . O2 O 0.13084(10) 0.25079(19) 0.39054(9) 0.0657(5) Uani 1 1 d . . . C1 C 0.21956(15) 0.2688(3) 0.39929(12) 0.0530(5) Uani 1 1 d . . . C8 C 0.23269(13) 0.1028(2) 0.28195(11) 0.0455(5) Uani 1 1 d . . . H8 H 0.1722 0.0840 0.2717 0.055 Uiso 1 1 calc R . . C6 C 0.38485(13) 0.1017(2) 0.27411(12) 0.0491(5) Uani 1 1 d . . . C7 C 0.30437(12) 0.0460(2) 0.23917(11) 0.0455(5) Uani 1 1 d . . . C10 C 0.29482(15) -0.0489(3) 0.16846(12) 0.0541(5) Uani 1 1 d . . . C11 C 0.20200(16) -0.0763(3) 0.13867(13) 0.0639(6) Uani 1 1 d . . . H11A H 0.2049 -0.1405 0.0927 0.096 Uiso 1 1 calc R . . H11B H 0.1743 0.0290 0.1282 0.096 Uiso 1 1 calc R . . H11C H 0.1671 -0.1351 0.1759 0.096 Uiso 1 1 calc R . . C2 C 0.26662(19) 0.3495(3) 0.45377(13) 0.0654(7) Uani 1 1 d . . . H2 H 0.2364 0.4018 0.4934 0.078 Uiso 1 1 calc R . . C3 C 0.36153(19) 0.3549(3) 0.45092(14) 0.0693(7) Uani 1 1 d . . . H3 H 0.3928 0.4117 0.4886 0.083 Uiso 1 1 calc R . . O1 O 0.35939(12) -0.1027(3) 0.13393(10) 0.0868(6) Uani 1 1 d . . . C4 C 0.40722(16) 0.2798(3) 0.39511(13) 0.0614(6) Uani 1 1 d . . . H4 H 0.4696 0.2851 0.3941 0.074 Uiso 1 1 calc R . . C9 C 0.47987(14) 0.0715(3) 0.24988(15) 0.0764(7) Uani 1 1 d . . . H9A H 0.5194 0.1414 0.2788 0.115 Uiso 1 1 calc R . . H9B H 0.4860 0.0966 0.1968 0.115 Uiso 1 1 calc R . . H9C H 0.4951 -0.0429 0.2585 0.115 Uiso 1 1 calc R . . C12 C 0.07536(19) 0.3172(3) 0.44983(16) 0.0884(9) Uani 1 1 d . . . H12A H 0.0910 0.2661 0.4973 0.133 Uiso 1 1 calc R . . H12B H 0.0134 0.2950 0.4385 0.133 Uiso 1 1 calc R . . H12C H 0.0845 0.4351 0.4533 0.133 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 0.0451(9) 0.0463(9) 0.0396(9) 0.0064(7) 0.0041(7) 0.0023(7) C5 0.0447(11) 0.0487(11) 0.0504(12) 0.0122(9) -0.0009(9) 0.0017(9) O2 0.0593(10) 0.0736(10) 0.0642(10) 0.0018(8) 0.0217(8) 0.0091(8) C1 0.0621(14) 0.0494(12) 0.0474(12) 0.0104(10) 0.0122(10) 0.0064(10) C8 0.0401(11) 0.0506(11) 0.0457(10) 0.0076(9) 0.0013(9) -0.0004(9) C6 0.0407(11) 0.0511(11) 0.0554(12) 0.0116(9) 0.0050(9) 0.0055(9) C7 0.0436(11) 0.0478(11) 0.0452(11) 0.0085(9) 0.0061(9) 0.0038(9) C10 0.0605(13) 0.0537(12) 0.0481(12) 0.0044(10) 0.0082(10) 0.0045(10) C11 0.0787(16) 0.0630(14) 0.0499(13) -0.0005(11) -0.0007(11) -0.0020(12) C2 0.097(2) 0.0537(13) 0.0453(12) 0.0013(10) 0.0073(12) 0.0034(13) C3 0.091(2) 0.0619(15) 0.0549(14) 0.0020(12) -0.0139(13) -0.0095(13) O1 0.0759(12) 0.1100(15) 0.0744(12) -0.0246(10) 0.0205(9) 0.0132(11) C4 0.0609(14) 0.0608(14) 0.0626(14) 0.0111(12) -0.0136(11) -0.0053(11) C9 0.0456(13) 0.0857(17) 0.0981(19) -0.0032(15) 0.0103(12) 0.0047(12) C12 0.0858(19) 0.094(2) 0.0851(19) 0.0049(16) 0.0436(16) 0.0204(16) _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 1.355(2) . ? N1 C1 1.382(3) . ? N1 C5 1.407(2) . ? C5 C6 1.382(3) . ? C5 C4 1.417(3) . ? O2 C1 1.337(3) . ? O2 C12 1.434(3) . ? C1 C2 1.353(3) . ? C8 C7 1.383(3) . ? C8 H8 0.9300 . ? C6 C7 1.419(3) . ? C6 C9 1.497(3) . ? C7 C10 1.467(3) . ? C10 O1 1.217(3) . ? C10 C11 1.494(3) . ? C11 H11A 0.9600 . ? C11 H11B 0.9600 . ? C11 H11C 0.9600 . ? C2 C3 1.414(4) . ? C2 H2 0.9300 . ? C3 C4 1.338(3) . ? C3 H3 0.9300 . ? C4 H4 0.9300 . ? C9 H9A 0.9600 . ? C9 H9B 0.9600 . ? C9 H9C 0.9600 . ? C12 H12A 0.9600 . ? C12 H12B 0.9600 . ? C12 H12C 0.9600 . ? 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 C8 N1 C1 128.59(18) . . ? C8 N1 C5 109.43(16) . . ? C1 N1 C5 121.98(18) . . ? C6 C5 N1 107.29(17) . . ? C6 C5 C4 135.2(2) . . ? N1 C5 C4 117.52(19) . . ? C1 O2 C12 116.4(2) . . ? O2 C1 C2 130.1(2) . . ? O2 C1 N1 111.03(19) . . ? C2 C1 N1 118.8(2) . . ? N1 C8 C7 108.07(17) . . ? N1 C8 H8 126.0 . . ? C7 C8 H8 126.0 . . ? C5 C6 C7 107.06(17) . . ? C5 C6 C9 124.4(2) . . ? C7 C6 C9 128.5(2) . . ? C8 C7 C6 108.15(18) . . ? C8 C7 C10 123.96(18) . . ? C6 C7 C10 127.85(18) . . ? O1 C10 C7 122.1(2) . . ? O1 C10 C11 120.2(2) . . ? C7 C10 C11 117.66(18) . . ? C10 C11 H11A 109.5 . . ? C10 C11 H11B 109.5 . . ? H11A C11 H11B 109.5 . . ? C10 C11 H11C 109.5 . . ? H11A C11 H11C 109.5 . . ? H11B C11 H11C 109.5 . . ? C1 C2 C3 120.4(2) . . ? C1 C2 H2 119.8 . . ? C3 C2 H2 119.8 . . ? C4 C3 C2 121.3(2) . . ? C4 C3 H3 119.3 . . ? C2 C3 H3 119.3 . . ? C3 C4 C5 119.9(2) . . ? C3 C4 H4 120.1 . . ? C5 C4 H4 120.1 . . ? C6 C9 H9A 109.5 . . ? C6 C9 H9B 109.5 . . ? H9A C9 H9B 109.5 . . ? C6 C9 H9C 109.5 . . ? H9A C9 H9C 109.5 . . ? H9B C9 H9C 109.5 . . ? O2 C12 H12A 109.5 . . ? O2 C12 H12B 109.5 . . ? H12A C12 H12B 109.5 . . ? O2 C12 H12C 109.5 . . ? H12A C12 H12C 109.5 . . ? H12B C12 H12C 109.5 . . ? _diffrn_measured_fraction_theta_max 1.000 _diffrn_reflns_theta_full 26.03 _diffrn_measured_fraction_theta_full 1.000 _refine_diff_density_max 0.158 _refine_diff_density_min -0.162 _refine_diff_density_rms 0.036 _database_code_depnum_ccdc_archive 'CCDC 950620' ####################################################################### # # 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_4f _audit_creation_method SHELXL-97 _chemical_name_systematic ; 8-Acetyl-1-aza-2-Methoxy-7-methyl-9-(3-oxobutyl)bicyclo[4.3.0]nona-2,4,6,8-tetraene ; _chemical_name_common ? _chemical_melting_point 129-131 _chemical_formula_moiety ? _chemical_formula_sum 'C16 H19 N O3' _chemical_formula_weight 273.32 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Monoclinic _symmetry_space_group_name_H-M 'P2(1) ' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y+1/2, -z' _cell_length_a 4.9759(15) _cell_length_b 13.292(4) _cell_length_c 10.625(3) _cell_angle_alpha 90.00 _cell_angle_beta 90.818(5) _cell_angle_gamma 90.00 _cell_volume 702.7(4) _cell_formula_units_Z 2 _cell_measurement_temperature 298(2) _cell_measurement_reflns_used 2461 _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description block _exptl_crystal_colour yellow _exptl_crystal_size_max 0.23 _exptl_crystal_size_mid 0.20 _exptl_crystal_size_min 0.18 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.292 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 292 _exptl_absorpt_coefficient_mu 0.089 _exptl_absorpt_correction_type none _exptl_absorpt_correction_T_min ? _exptl_absorpt_correction_T_max ? _exptl_absorpt_process_details ? _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 7205 _diffrn_reflns_av_R_equivalents 0.0294 _diffrn_reflns_av_sigmaI/netI 0.0381 _diffrn_reflns_limit_h_min -6 _diffrn_reflns_limit_h_max 6 _diffrn_reflns_limit_k_min -16 _diffrn_reflns_limit_k_max 16 _diffrn_reflns_limit_l_min -13 _diffrn_reflns_limit_l_max 13 _diffrn_reflns_theta_min 1.92 _diffrn_reflns_theta_max 26.02 _reflns_number_total 2749 _reflns_number_gt 2311 _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 'Bruker SHELXTL' _computing_publication_material 'Bruker SHELXTL' _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0655P)^2^+0.0487P] 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_number_reflns 2749 _refine_ls_number_parameters 185 _refine_ls_number_restraints 1 _refine_ls_R_factor_all 0.0552 _refine_ls_R_factor_gt 0.0462 _refine_ls_wR_factor_ref 0.1238 _refine_ls_wR_factor_gt 0.1194 _refine_ls_goodness_of_fit_ref 1.090 _refine_ls_restrained_S_all 1.089 _refine_ls_shift/su_max 0.000 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group O1 O 0.1131(4) 0.09661(13) 0.62718(17) 0.0559(5) Uani 1 1 d . . . N1 N 0.4461(4) 0.16568(14) 0.74703(17) 0.0405(4) Uani 1 1 d . . . C1 C 0.2837(5) 0.08230(18) 0.7247(2) 0.0455(6) Uani 1 1 d . . . C8 C 0.4621(5) 0.25739(17) 0.6860(2) 0.0408(5) Uani 1 1 d . . . C5 C 0.6299(5) 0.1655(2) 0.8507(2) 0.0463(6) Uani 1 1 d . . . O3 O 0.1187(4) 0.28425(18) 0.31462(19) 0.0732(6) Uani 1 1 d . . . C6 C 0.7593(5) 0.2565(2) 0.8533(2) 0.0481(6) Uani 1 1 d . . . C13 C 0.3237(5) 0.28021(18) 0.5636(2) 0.0436(5) Uani 1 1 d . . . H13A H 0.3182 0.3525 0.5512 0.052 Uiso 1 1 calc R . . H13B H 0.1400 0.2559 0.5662 0.052 Uiso 1 1 calc R . . C7 C 0.6548(4) 0.31467(18) 0.7514(2) 0.0420(5) Uani 1 1 d . . . C3 C 0.4910(7) -0.0031(2) 0.8992(3) 0.0672(8) Uani 1 1 d . . . H3 H 0.5055 -0.0607 0.9486 0.081 Uiso 1 1 calc R . . C11 C 0.7261(5) 0.4192(2) 0.7180(3) 0.0525(6) Uani 1 1 d . . . O2 O 0.5993(5) 0.46643(18) 0.6386(2) 0.0879(8) Uani 1 1 d . . . C9 C -0.0542(6) 0.0132(2) 0.5909(3) 0.0659(8) Uani 1 1 d . . . H9A H 0.0567 -0.0436 0.5713 0.099 Uiso 1 1 calc R . . H9B H -0.1602 0.0313 0.5181 0.099 Uiso 1 1 calc R . . H9C H -0.1708 -0.0037 0.6589 0.099 Uiso 1 1 calc R . . C15 C 0.3374(5) 0.24590(19) 0.3271(2) 0.0480(6) Uani 1 1 d . . . C14 C 0.4670(5) 0.2313(2) 0.4537(2) 0.0500(6) Uani 1 1 d . . . H14A H 0.6485 0.2577 0.4510 0.060 Uiso 1 1 calc R . . H14B H 0.4805 0.1596 0.4700 0.060 Uiso 1 1 calc R . . C2 C 0.3050(6) -0.0002(2) 0.7978(3) 0.0614(7) Uani 1 1 d . . . H2 H 0.1962 -0.0557 0.7813 0.074 Uiso 1 1 calc R . . C4 C 0.6479(6) 0.0772(2) 0.9249(2) 0.0589(7) Uani 1 1 d . . . H4 H 0.7694 0.0746 0.9921 0.071 Uiso 1 1 calc R . . C10 C 0.9739(6) 0.2803(3) 0.9509(3) 0.0652(8) Uani 1 1 d . . . H10A H 0.9865 0.2261 1.0103 0.098 Uiso 1 1 calc R . . H10B H 0.9281 0.3413 0.9940 0.098 Uiso 1 1 calc R . . H10C H 1.1436 0.2887 0.9103 0.098 Uiso 1 1 calc R . . C16 C 0.4919(6) 0.2105(3) 0.2166(2) 0.0634(7) Uani 1 1 d . . . H16A H 0.3904 0.2234 0.1408 0.095 Uiso 1 1 calc R . . H16B H 0.5247 0.1395 0.2242 0.095 Uiso 1 1 calc R . . H16C H 0.6603 0.2456 0.2136 0.095 Uiso 1 1 calc R . . C12 C 0.9559(7) 0.4702(3) 0.7821(4) 0.0753(9) Uani 1 1 d . . . H12A H 0.9789 0.5361 0.7470 0.113 Uiso 1 1 calc R . . H12B H 1.1166 0.4315 0.7703 0.113 Uiso 1 1 calc R . . H12C H 0.9207 0.4758 0.8704 0.113 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 0.0596(11) 0.0512(10) 0.0565(10) -0.0016(9) -0.0114(9) -0.0086(8) N1 0.0431(10) 0.0414(10) 0.0370(10) -0.0009(8) -0.0016(8) 0.0031(8) C1 0.0468(14) 0.0457(13) 0.0441(13) -0.0007(10) 0.0072(11) -0.0002(11) C8 0.0416(11) 0.0433(13) 0.0375(11) -0.0035(10) 0.0010(9) 0.0037(10) C5 0.0449(13) 0.0591(15) 0.0347(12) -0.0004(11) -0.0008(10) 0.0091(12) O3 0.0627(12) 0.0985(16) 0.0577(11) -0.0074(11) -0.0191(9) 0.0220(12) C6 0.0389(12) 0.0676(16) 0.0379(11) -0.0059(12) 0.0010(9) 0.0065(12) C13 0.0475(13) 0.0412(12) 0.0420(12) 0.0003(10) -0.0071(10) 0.0020(10) C7 0.0388(12) 0.0491(13) 0.0381(12) -0.0074(10) 0.0009(10) -0.0001(10) C3 0.077(2) 0.0612(18) 0.0639(18) 0.0226(15) 0.0034(16) 0.0090(15) C11 0.0512(14) 0.0535(14) 0.0528(15) -0.0065(13) 0.0048(12) -0.0029(12) O2 0.1005(18) 0.0632(13) 0.0992(18) 0.0249(13) -0.0305(15) -0.0242(13) C9 0.0610(16) 0.0579(17) 0.079(2) -0.0131(15) -0.0054(16) -0.0105(13) C15 0.0458(13) 0.0525(14) 0.0454(13) -0.0010(11) -0.0084(10) -0.0064(11) C14 0.0464(13) 0.0611(15) 0.0423(12) -0.0007(12) -0.0035(10) 0.0074(11) C2 0.0635(16) 0.0507(16) 0.0702(18) 0.0075(14) 0.0065(15) -0.0025(13) C4 0.0590(16) 0.0739(19) 0.0439(14) 0.0087(13) -0.0004(12) 0.0166(15) C10 0.0516(15) 0.096(2) 0.0471(14) -0.0093(15) -0.0091(11) 0.0009(15) C16 0.0673(17) 0.0839(19) 0.0389(13) -0.0050(13) -0.0013(13) 0.0037(15) C12 0.0654(18) 0.0676(19) 0.093(2) -0.0108(17) -0.0048(17) -0.0192(16) _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 C1 1.344(3) . ? O1 C9 1.435(3) . ? N1 C8 1.384(3) . ? N1 C1 1.390(3) . ? N1 C5 1.421(3) . ? C1 C2 1.347(4) . ? C8 C7 1.401(3) . ? C8 C13 1.493(3) . ? C5 C6 1.371(4) . ? C5 C4 1.416(4) . ? O3 C15 1.207(3) . ? C6 C7 1.422(4) . ? C6 C10 1.511(3) . ? C13 C14 1.523(3) . ? C13 H13A 0.9700 . ? C13 H13B 0.9700 . ? C7 C11 1.478(4) . ? C3 C4 1.348(5) . ? C3 C2 1.411(5) . ? C3 H3 0.9300 . ? C11 O2 1.220(3) . ? C11 C12 1.486(4) . ? C9 H9A 0.9600 . ? C9 H9B 0.9600 . ? C9 H9C 0.9600 . ? C15 C16 1.489(4) . ? C15 C14 1.497(3) . ? C14 H14A 0.9700 . ? C14 H14B 0.9700 . ? C2 H2 0.9300 . ? C4 H4 0.9300 . ? C10 H10A 0.9600 . ? C10 H10B 0.9600 . ? C10 H10C 0.9600 . ? C16 H16A 0.9600 . ? C16 H16B 0.9600 . ? C16 H16C 0.9600 . ? C12 H12A 0.9600 . ? C12 H12B 0.9600 . ? C12 H12C 0.9600 . ? 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 C1 O1 C9 117.1(2) . . ? C8 N1 C1 131.27(19) . . ? C8 N1 C5 108.92(19) . . ? C1 N1 C5 119.8(2) . . ? O1 C1 C2 127.1(2) . . ? O1 C1 N1 112.22(19) . . ? C2 C1 N1 120.7(2) . . ? N1 C8 C7 106.84(19) . . ? N1 C8 C13 123.9(2) . . ? C7 C8 C13 128.7(2) . . ? C6 C5 C4 134.0(2) . . ? C6 C5 N1 108.1(2) . . ? C4 C5 N1 117.9(2) . . ? C5 C6 C7 107.3(2) . . ? C5 C6 C10 121.7(2) . . ? C7 C6 C10 131.0(3) . . ? C8 C13 C14 111.43(19) . . ? C8 C13 H13A 109.3 . . ? C14 C13 H13A 109.3 . . ? C8 C13 H13B 109.3 . . ? C14 C13 H13B 109.3 . . ? H13A C13 H13B 108.0 . . ? C8 C7 C6 108.8(2) . . ? C8 C7 C11 123.8(2) . . ? C6 C7 C11 127.4(2) . . ? C4 C3 C2 120.2(3) . . ? C4 C3 H3 119.9 . . ? C2 C3 H3 119.9 . . ? O2 C11 C7 121.7(2) . . ? O2 C11 C12 118.0(3) . . ? C7 C11 C12 120.3(3) . . ? O1 C9 H9A 109.5 . . ? O1 C9 H9B 109.5 . . ? H9A C9 H9B 109.5 . . ? O1 C9 H9C 109.5 . . ? H9A C9 H9C 109.5 . . ? H9B C9 H9C 109.5 . . ? O3 C15 C16 121.5(2) . . ? O3 C15 C14 122.0(2) . . ? C16 C15 C14 116.5(2) . . ? C15 C14 C13 115.7(2) . . ? C15 C14 H14A 108.4 . . ? C13 C14 H14A 108.4 . . ? C15 C14 H14B 108.4 . . ? C13 C14 H14B 108.4 . . ? H14A C14 H14B 107.4 . . ? C1 C2 C3 120.6(3) . . ? C1 C2 H2 119.7 . . ? C3 C2 H2 119.7 . . ? C3 C4 C5 120.8(2) . . ? C3 C4 H4 119.6 . . ? C5 C4 H4 119.6 . . ? C6 C10 H10A 109.5 . . ? C6 C10 H10B 109.5 . . ? H10A C10 H10B 109.5 . . ? C6 C10 H10C 109.5 . . ? H10A C10 H10C 109.5 . . ? H10B C10 H10C 109.5 . . ? C15 C16 H16A 109.5 . . ? C15 C16 H16B 109.5 . . ? H16A C16 H16B 109.5 . . ? C15 C16 H16C 109.5 . . ? H16A C16 H16C 109.5 . . ? H16B C16 H16C 109.5 . . ? C11 C12 H12A 109.5 . . ? C11 C12 H12B 109.5 . . ? H12A C12 H12B 109.5 . . ? C11 C12 H12C 109.5 . . ? H12A C12 H12C 109.5 . . ? H12B C12 H12C 109.5 . . ? _diffrn_measured_fraction_theta_max 0.996 _diffrn_reflns_theta_full 26.02 _diffrn_measured_fraction_theta_full 0.996 _refine_diff_density_max 0.130 _refine_diff_density_min -0.178 _refine_diff_density_rms 0.039 _database_code_depnum_ccdc_archive 'CCDC 950621'