data_global _journal_name_full Org.Biomol.Chem. _journal_coden_Cambridge 0177 _journal_volume ? _journal_page_first ? _journal_year ? _publ_contact_author_name 'Frank King' _publ_contact_author_email FD.KING@BTINTERNET.COM _publ_section_title ; A Facile Synthesis of Pyrrolo-(di)-benzazocinones via an Intramolecular N-Acyliminium Ion Cyclisation ; loop_ _publ_author_name 'Frank King' 'Abil E. Aliev' 'Stephen Caddick' 'Denis Courtier-Murias' 'Derek A. Tocher' # Attachment 'STR0633 diMeO5c.CIF' data_str0633 _database_code_depnum_ccdc_archive 'CCDC 690260' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C16 H21 N O3' _chemical_formula_weight 275.34 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting triclinic _symmetry_space_group_name_H-M P-1 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 8.3607(11) _cell_length_b 9.2365(13) _cell_length_c 10.0371(14) _cell_angle_alpha 65.628(2) _cell_angle_beta 77.548(2) _cell_angle_gamma 75.070(2) _cell_volume 676.91(16) _cell_formula_units_Z 2 _cell_measurement_temperature 150(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 0.50 _exptl_crystal_size_mid 0.34 _exptl_crystal_size_min 0.28 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.351 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 296 _exptl_absorpt_coefficient_mu 0.093 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.9551 _exptl_absorpt_correction_T_max 0.9745 _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 150(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Bruker SMART APEX CCD diffractometer' _diffrn_measurement_method '\w rotation with narrow frames' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 5715 _diffrn_reflns_av_R_equivalents 0.0207 _diffrn_reflns_av_sigmaI/netI 0.0299 _diffrn_reflns_limit_h_min -11 _diffrn_reflns_limit_h_max 11 _diffrn_reflns_limit_k_min -12 _diffrn_reflns_limit_k_max 12 _diffrn_reflns_limit_l_min -13 _diffrn_reflns_limit_l_max 13 _diffrn_reflns_theta_min 2.63 _diffrn_reflns_theta_max 28.24 _reflns_number_total 3056 _reflns_number_gt 2808 _reflns_threshold_expression I>2\s(I) _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'Bruker SAINT' _computing_data_reduction 'Bruker SAINT' _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^)+(0.1037P)^2^+0.2467P] 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 3056 _refine_ls_number_parameters 181 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0520 _refine_ls_R_factor_gt 0.0494 _refine_ls_wR_factor_ref 0.1496 _refine_ls_wR_factor_gt 0.1463 _refine_ls_goodness_of_fit_ref 0.986 _refine_ls_restrained_S_all 0.986 _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 0.06445(13) 0.25902(13) 0.35025(12) 0.0189(2) Uani 1 1 d . . . O1 O 0.19896(13) 0.35794(13) 0.45718(11) 0.0284(3) Uani 1 1 d . . . O2 O 0.42796(12) 0.33551(12) -0.17836(10) 0.0243(2) Uani 1 1 d . . . O3 O 0.06475(12) -0.11469(11) 0.23109(10) 0.0226(2) Uani 1 1 d . . . C1 C 0.20353(16) 0.27174(16) 0.38950(14) 0.0201(3) Uani 1 1 d . . . C2 C 0.36867(16) 0.19562(16) 0.32734(15) 0.0221(3) Uani 1 1 d . . . H2A H 0.3579 0.0970 0.3164 0.027 Uiso 1 1 calc R . . H2B H 0.4544 0.1656 0.3933 0.027 Uiso 1 1 calc R . . C3 C 0.41731(16) 0.32391(16) 0.17577(15) 0.0230(3) Uani 1 1 d . . . H3A H 0.4379 0.4170 0.1903 0.028 Uiso 1 1 calc R . . H3B H 0.5225 0.2769 0.1286 0.028 Uiso 1 1 calc R . . C4 C 0.28198(16) 0.38498(15) 0.07194(14) 0.0203(3) Uani 1 1 d . . . H4A H 0.1772 0.4355 0.1167 0.024 Uiso 1 1 calc R . . H4B H 0.3184 0.4680 -0.0229 0.024 Uiso 1 1 calc R . . C5 C 0.25143(15) 0.24554(14) 0.04496(13) 0.0171(3) Uani 1 1 d . . . C6 C 0.33678(16) 0.21969(15) -0.08320(14) 0.0195(3) Uani 1 1 d . . . C7 C 0.32964(17) 0.08491(17) -0.10781(15) 0.0224(3) Uani 1 1 d . . . H7A H 0.3858 0.0704 -0.1957 0.027 Uiso 1 1 calc R . . C8 C 0.23970(16) -0.02919(16) -0.00312(15) 0.0218(3) Uani 1 1 d . . . H8A H 0.2367 -0.1232 -0.0185 0.026 Uiso 1 1 calc R . . C9 C 0.15479(15) -0.00666(15) 0.12291(14) 0.0185(3) Uani 1 1 d . . . C10 C 0.15699(15) 0.13270(14) 0.14836(13) 0.0167(3) Uani 1 1 d . . . C11 C 0.04689(15) 0.14447(14) 0.28745(13) 0.0169(3) Uani 1 1 d . . . H11A H 0.0618 0.0337 0.3667 0.020 Uiso 1 1 calc R . . C12 C -0.13861(16) 0.19580(17) 0.26338(15) 0.0228(3) Uani 1 1 d . . . H12A H -0.1534 0.2798 0.1638 0.027 Uiso 1 1 calc R . . H12B H -0.1844 0.1019 0.2751 0.027 Uiso 1 1 calc R . . C13 C -0.22361(16) 0.26247(16) 0.38203(14) 0.0222(3) Uani 1 1 d . . . H13A H -0.3312 0.3358 0.3554 0.027 Uiso 1 1 calc R . . H13B H -0.2432 0.1741 0.4786 0.027 Uiso 1 1 calc R . . C14 C -0.09830(17) 0.35362(18) 0.38480(17) 0.0263(3) Uani 1 1 d . . . H14A H -0.1145 0.4654 0.3100 0.032 Uiso 1 1 calc R . . H14B H -0.1080 0.3580 0.4832 0.032 Uiso 1 1 calc R . . C15 C 0.50756(18) 0.31861(18) -0.31345(14) 0.0264(3) Uani 1 1 d . . . H15A H 0.5679 0.4075 -0.3716 0.040 Uiso 1 1 calc R . . H15B H 0.4232 0.3216 -0.3693 0.040 Uiso 1 1 calc R . . H15C H 0.5862 0.2151 -0.2921 0.040 Uiso 1 1 calc R . . C16 C 0.06780(19) -0.26165(16) 0.21404(16) 0.0257(3) Uani 1 1 d . . . H16A H -0.0016 -0.3276 0.2975 0.039 Uiso 1 1 calc R . . H16B H 0.1828 -0.3219 0.2109 0.039 Uiso 1 1 calc R . . H16C H 0.0243 -0.2362 0.1221 0.039 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 0.0168(5) 0.0223(5) 0.0205(5) -0.0119(4) -0.0012(4) -0.0031(4) O1 0.0281(5) 0.0362(6) 0.0303(5) -0.0205(5) -0.0033(4) -0.0087(4) O2 0.0274(5) 0.0259(5) 0.0189(5) -0.0089(4) 0.0050(4) -0.0097(4) O3 0.0284(5) 0.0166(4) 0.0249(5) -0.0082(4) -0.0009(4) -0.0091(4) C1 0.0221(6) 0.0218(6) 0.0175(6) -0.0071(5) -0.0032(4) -0.0061(5) C2 0.0178(6) 0.0248(6) 0.0259(7) -0.0107(5) -0.0053(5) -0.0038(5) C3 0.0201(6) 0.0256(6) 0.0275(7) -0.0137(5) 0.0013(5) -0.0090(5) C4 0.0237(6) 0.0163(6) 0.0207(6) -0.0068(5) 0.0012(5) -0.0070(5) C5 0.0171(6) 0.0159(5) 0.0178(6) -0.0061(5) -0.0036(4) -0.0016(4) C6 0.0179(6) 0.0205(6) 0.0178(6) -0.0055(5) -0.0022(4) -0.0029(5) C7 0.0217(6) 0.0270(7) 0.0207(6) -0.0134(5) -0.0002(5) -0.0026(5) C8 0.0227(6) 0.0202(6) 0.0263(6) -0.0133(5) -0.0047(5) -0.0017(5) C9 0.0184(6) 0.0168(6) 0.0203(6) -0.0059(5) -0.0048(5) -0.0032(4) C10 0.0165(6) 0.0168(6) 0.0170(6) -0.0066(5) -0.0033(4) -0.0020(4) C11 0.0178(6) 0.0160(5) 0.0170(5) -0.0056(4) -0.0017(4) -0.0048(4) C12 0.0175(6) 0.0283(7) 0.0274(7) -0.0150(5) -0.0031(5) -0.0046(5) C13 0.0183(6) 0.0256(6) 0.0234(6) -0.0115(5) -0.0003(5) -0.0035(5) C14 0.0185(6) 0.0308(7) 0.0372(8) -0.0229(6) -0.0018(5) -0.0016(5) C15 0.0261(7) 0.0325(7) 0.0172(6) -0.0077(5) 0.0015(5) -0.0060(5) C16 0.0327(7) 0.0160(6) 0.0318(7) -0.0087(5) -0.0082(6) -0.0074(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 N1 C1 1.3517(16) . ? N1 C14 1.4729(16) . ? N1 C11 1.4862(15) . ? O1 C1 1.2314(16) . ? O2 C6 1.3786(15) . ? O2 C15 1.4275(16) . ? O3 C9 1.3718(15) . ? O3 C16 1.4299(15) . ? C1 C2 1.5100(18) . ? C2 C3 1.5419(19) . ? C3 C4 1.5424(18) . ? C4 C5 1.5115(16) . ? C5 C10 1.4017(17) . ? C5 C6 1.4109(17) . ? C6 C7 1.3830(19) . ? C7 C8 1.3907(19) . ? C8 C9 1.3789(19) . ? C9 C10 1.4171(17) . ? C10 C11 1.5257(16) . ? C11 C12 1.5417(17) . ? C12 C13 1.5223(18) . ? C13 C14 1.5145(18) . ? 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 C14 119.89(11) . . ? C1 N1 C11 128.04(11) . . ? C14 N1 C11 111.72(10) . . ? C6 O2 C15 116.93(11) . . ? C9 O3 C16 117.38(10) . . ? O1 C1 N1 122.06(12) . . ? O1 C1 C2 120.40(12) . . ? N1 C1 C2 116.93(11) . . ? C1 C2 C3 106.32(10) . . ? C4 C3 C2 112.85(10) . . ? C5 C4 C3 110.00(10) . . ? C10 C5 C6 119.14(11) . . ? C10 C5 C4 122.79(11) . . ? C6 C5 C4 117.72(11) . . ? C7 C6 O2 123.38(12) . . ? C7 C6 C5 121.20(12) . . ? O2 C6 C5 115.42(11) . . ? C6 C7 C8 119.56(12) . . ? C9 C8 C7 120.40(12) . . ? O3 C9 C8 123.47(11) . . ? O3 C9 C10 115.63(11) . . ? C8 C9 C10 120.89(12) . . ? C5 C10 C9 118.76(11) . . ? C5 C10 C11 127.10(11) . . ? C9 C10 C11 114.10(10) . . ? N1 C11 C10 121.06(10) . . ? N1 C11 C12 102.19(10) . . ? C10 C11 C12 110.65(10) . . ? C13 C12 C11 104.40(10) . . ? C14 C13 C12 102.65(10) . . ? N1 C14 C13 103.98(10) . . ? 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 C14 N1 C1 O1 1.74(19) . . . . ? C11 N1 C1 O1 -170.88(12) . . . . ? C14 N1 C1 C2 -169.33(12) . . . . ? C11 N1 C1 C2 18.04(18) . . . . ? O1 C1 C2 C3 -84.87(14) . . . . ? N1 C1 C2 C3 86.36(14) . . . . ? C1 C2 C3 C4 -55.80(14) . . . . ? C2 C3 C4 C5 -60.16(14) . . . . ? C3 C4 C5 C10 77.37(14) . . . . ? C3 C4 C5 C6 -95.78(13) . . . . ? C15 O2 C6 C7 4.81(18) . . . . ? C15 O2 C6 C5 -176.25(11) . . . . ? C10 C5 C6 C7 -0.43(19) . . . . ? C4 C5 C6 C7 172.98(12) . . . . ? C10 C5 C6 O2 -179.39(10) . . . . ? C4 C5 C6 O2 -5.98(16) . . . . ? O2 C6 C7 C8 177.51(11) . . . . ? C5 C6 C7 C8 -1.4(2) . . . . ? C6 C7 C8 C9 1.5(2) . . . . ? C16 O3 C9 C8 3.40(18) . . . . ? C16 O3 C9 C10 -176.23(10) . . . . ? C7 C8 C9 O3 -179.50(11) . . . . ? C7 C8 C9 C10 0.11(19) . . . . ? C6 C5 C10 C9 2.03(18) . . . . ? C4 C5 C10 C9 -171.03(11) . . . . ? C6 C5 C10 C11 -175.46(11) . . . . ? C4 C5 C10 C11 11.48(19) . . . . ? O3 C9 C10 C5 177.74(10) . . . . ? C8 C9 C10 C5 -1.90(18) . . . . ? O3 C9 C10 C11 -4.45(15) . . . . ? C8 C9 C10 C11 175.90(11) . . . . ? C1 N1 C11 C10 -54.83(17) . . . . ? C14 N1 C11 C10 132.05(12) . . . . ? C1 N1 C11 C12 -178.29(12) . . . . ? C14 N1 C11 C12 8.60(13) . . . . ? C5 C10 C11 N1 -17.16(18) . . . . ? C9 C10 C11 N1 165.26(10) . . . . ? C5 C10 C11 C12 102.21(14) . . . . ? C9 C10 C11 C12 -75.37(13) . . . . ? N1 C11 C12 C13 -29.31(12) . . . . ? C10 C11 C12 C13 -159.52(10) . . . . ? C11 C12 C13 C14 39.18(13) . . . . ? C1 N1 C14 C13 -158.26(11) . . . . ? C11 N1 C14 C13 15.49(14) . . . . ? C12 C13 C14 N1 -33.23(13) . . . . ? _diffrn_measured_fraction_theta_max 0.911 _diffrn_reflns_theta_full 26.00 _diffrn_measured_fraction_theta_full 0.976 _refine_diff_density_max 0.329 _refine_diff_density_min -0.382 _refine_diff_density_rms 0.083 # Attachment 'STR0648phenylbenzazocine8.CIF' data_str0648 _database_code_depnum_ccdc_archive 'CCDC 703700' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C20 H21 N O' _chemical_formula_weight 291.38 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M P2(1)/c loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y-1/2, z-1/2' _cell_length_a 7.6569(8) _cell_length_b 9.6582(11) _cell_length_c 20.404(2) _cell_angle_alpha 90.00 _cell_angle_beta 90.423(2) _cell_angle_gamma 90.00 _cell_volume 1508.9(3) _cell_formula_units_Z 4 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description block _exptl_crystal_colour colourless _exptl_crystal_size_max 0.48 _exptl_crystal_size_mid 0.46 _exptl_crystal_size_min 0.43 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.283 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 624 _exptl_absorpt_coefficient_mu 0.078 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.9634 _exptl_absorpt_correction_T_max 0.9671 _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 293(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Bruker SMART APEX CCD diffractometer' _diffrn_measurement_method '\w rotation with narrow frames' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 12268 _diffrn_reflns_av_R_equivalents 0.0327 _diffrn_reflns_av_sigmaI/netI 0.0283 _diffrn_reflns_limit_h_min -10 _diffrn_reflns_limit_h_max 10 _diffrn_reflns_limit_k_min -12 _diffrn_reflns_limit_k_max 12 _diffrn_reflns_limit_l_min -26 _diffrn_reflns_limit_l_max 26 _diffrn_reflns_theta_min 3.34 _diffrn_reflns_theta_max 28.29 _reflns_number_total 3580 _reflns_number_gt 3271 _reflns_threshold_expression I>2\s(I) _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'Bruker SAINT' _computing_data_reduction 'Bruker SAINT' _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^)+(0.0720P)^2^+0.4836P] 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 0.027(4) _refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^ _refine_ls_number_reflns 3580 _refine_ls_number_parameters 200 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0473 _refine_ls_R_factor_gt 0.0440 _refine_ls_wR_factor_ref 0.1231 _refine_ls_wR_factor_gt 0.1201 _refine_ls_goodness_of_fit_ref 1.041 _refine_ls_restrained_S_all 1.041 _refine_ls_shift/su_max 0.000 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group N1 N 0.33278(12) 0.38610(10) 0.46664(4) 0.0190(2) Uani 1 1 d . . . O1 O 0.19314(11) 0.55102(9) 0.40949(4) 0.0255(2) Uani 1 1 d . . . C1 C 0.19422(16) 0.39306(12) 0.51677(6) 0.0236(3) Uani 1 1 d . . . H1A H 0.0800 0.3793 0.4970 0.028 Uiso 1 1 calc R . . H1B H 0.1958 0.4820 0.5389 0.028 Uiso 1 1 calc R . . C2 C 0.23716(17) 0.27619(13) 0.56473(6) 0.0281(3) Uani 1 1 d . . . H2A H 0.2954 0.3118 0.6036 0.034 Uiso 1 1 calc R . . H2B H 0.1321 0.2276 0.5777 0.034 Uiso 1 1 calc R . . C3 C 0.35808(16) 0.18104(12) 0.52619(6) 0.0231(2) Uani 1 1 d . . . H3A H 0.2921 0.1197 0.4976 0.028 Uiso 1 1 calc R . . H3B H 0.4309 0.1260 0.5553 0.028 Uiso 1 1 calc R . . C4 C 0.46775(14) 0.28353(11) 0.48657(5) 0.0180(2) Uani 1 1 d . . . H4A H 0.5454 0.3304 0.5178 0.022 Uiso 1 1 calc R . . C5 C 0.58395(14) 0.21179(11) 0.43721(5) 0.0172(2) Uani 1 1 d . . . C6 C 0.75598(15) 0.18840(12) 0.45833(6) 0.0221(2) Uani 1 1 d . . . H6A H 0.7934 0.2251 0.4982 0.027 Uiso 1 1 calc R . . C7 C 0.87149(15) 0.11166(13) 0.42103(6) 0.0249(3) Uani 1 1 d . . . H7A H 0.9846 0.0961 0.4362 0.030 Uiso 1 1 calc R . . C8 C 0.81823(15) 0.05814(12) 0.36113(6) 0.0234(3) Uani 1 1 d . . . H8A H 0.8949 0.0064 0.3359 0.028 Uiso 1 1 calc R . . C9 C 0.64903(14) 0.08274(11) 0.33931(5) 0.0201(2) Uani 1 1 d . . . H9A H 0.6141 0.0482 0.2987 0.024 Uiso 1 1 calc R . . C10 C 0.52981(13) 0.15777(11) 0.37654(5) 0.0164(2) Uani 1 1 d . . . C11 C 0.35224(13) 0.19349(11) 0.34739(5) 0.0161(2) Uani 1 1 d . . . H11A H 0.2730 0.2087 0.3842 0.019 Uiso 1 1 calc R . . C12 C 0.27487(13) 0.07664(11) 0.30635(5) 0.0175(2) Uani 1 1 d . . . C13 C 0.26093(14) -0.05544(12) 0.33431(6) 0.0221(2) Uani 1 1 d . . . H13A H 0.3031 -0.0702 0.3766 0.026 Uiso 1 1 calc R . . C14 C 0.18540(15) -0.16456(12) 0.30008(7) 0.0265(3) Uani 1 1 d . . . H14A H 0.1785 -0.2519 0.3191 0.032 Uiso 1 1 calc R . . C15 C 0.12008(15) -0.14253(13) 0.23712(6) 0.0276(3) Uani 1 1 d . . . H15A H 0.0694 -0.2153 0.2139 0.033 Uiso 1 1 calc R . . C16 C 0.13046(15) -0.01259(14) 0.20903(6) 0.0263(3) Uani 1 1 d . . . H16A H 0.0850 0.0024 0.1672 0.032 Uiso 1 1 calc R . . C17 C 0.20911(14) 0.09626(12) 0.24329(5) 0.0216(2) Uani 1 1 d . . . H17A H 0.2176 0.1829 0.2237 0.026 Uiso 1 1 calc R . . C18 C 0.36976(14) 0.33309(11) 0.31128(5) 0.0189(2) Uani 1 1 d . . . H18A H 0.4488 0.3221 0.2747 0.023 Uiso 1 1 calc R . . H18B H 0.2566 0.3599 0.2938 0.023 Uiso 1 1 calc R . . C19 C 0.43871(14) 0.44886(11) 0.35660(5) 0.0195(2) Uani 1 1 d . . . H19A H 0.5540 0.4247 0.3729 0.023 Uiso 1 1 calc R . . H19B H 0.4479 0.5347 0.3322 0.023 Uiso 1 1 calc R . . C20 C 0.31519(14) 0.46775(11) 0.41343(5) 0.0185(2) Uani 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 N1 0.0203(5) 0.0172(4) 0.0194(4) -0.0006(3) 0.0018(3) 0.0027(3) O1 0.0280(4) 0.0221(4) 0.0265(4) 0.0004(3) -0.0017(3) 0.0073(3) C1 0.0257(6) 0.0234(6) 0.0218(5) -0.0006(4) 0.0059(4) 0.0035(4) C2 0.0348(7) 0.0277(6) 0.0220(6) 0.0032(5) 0.0081(5) 0.0049(5) C3 0.0276(6) 0.0214(5) 0.0204(5) 0.0039(4) 0.0027(4) 0.0026(4) C4 0.0185(5) 0.0178(5) 0.0177(5) -0.0012(4) -0.0035(4) 0.0009(4) C5 0.0167(5) 0.0152(5) 0.0198(5) 0.0018(4) -0.0004(4) -0.0006(4) C6 0.0191(5) 0.0213(5) 0.0258(6) 0.0022(4) -0.0045(4) -0.0023(4) C7 0.0140(5) 0.0255(6) 0.0351(6) 0.0062(5) -0.0013(4) 0.0010(4) C8 0.0189(5) 0.0206(5) 0.0307(6) 0.0038(4) 0.0067(4) 0.0025(4) C9 0.0202(5) 0.0184(5) 0.0217(5) 0.0009(4) 0.0033(4) 0.0004(4) C10 0.0155(5) 0.0150(5) 0.0186(5) 0.0023(4) 0.0003(4) -0.0011(4) C11 0.0159(5) 0.0170(5) 0.0155(5) -0.0009(4) -0.0003(4) 0.0005(4) C12 0.0141(5) 0.0192(5) 0.0192(5) -0.0033(4) 0.0014(4) 0.0014(4) C13 0.0191(5) 0.0213(5) 0.0257(6) 0.0001(4) -0.0022(4) 0.0008(4) C14 0.0197(5) 0.0195(5) 0.0404(7) -0.0037(5) 0.0008(5) 0.0007(4) C15 0.0196(5) 0.0279(6) 0.0353(7) -0.0152(5) 0.0027(5) -0.0022(4) C16 0.0222(5) 0.0362(7) 0.0204(5) -0.0092(5) 0.0006(4) -0.0018(5) C17 0.0211(5) 0.0249(6) 0.0188(5) -0.0019(4) 0.0016(4) -0.0004(4) C18 0.0210(5) 0.0185(5) 0.0173(5) 0.0017(4) 0.0003(4) 0.0005(4) C19 0.0211(5) 0.0164(5) 0.0211(5) 0.0029(4) 0.0010(4) -0.0014(4) C20 0.0210(5) 0.0142(5) 0.0204(5) -0.0016(4) -0.0025(4) -0.0019(4) _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 C20 1.3478(14) . ? N1 C1 1.4808(14) . ? N1 C4 1.4861(14) . ? O1 C20 1.2352(14) . ? C1 C2 1.5281(17) . ? C2 C3 1.5267(16) . ? C3 C4 1.5324(15) . ? C4 C5 1.5164(15) . ? C5 C6 1.4013(15) . ? C5 C10 1.4032(15) . ? C6 C7 1.3859(17) . ? C7 C8 1.3857(18) . ? C8 C9 1.3873(16) . ? C9 C10 1.3949(15) . ? C10 C11 1.5196(14) . ? C11 C12 1.5228(14) . ? C11 C18 1.5428(14) . ? C12 C17 1.3911(15) . ? C12 C13 1.4018(16) . ? C13 C14 1.3882(16) . ? C14 C15 1.3913(19) . ? C15 C16 1.3823(19) . ? C16 C17 1.3966(16) . ? C18 C19 1.5418(15) . ? C19 C20 1.5126(15) . ? 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 C20 N1 C1 117.52(9) . . ? C20 N1 C4 132.51(9) . . ? C1 N1 C4 109.96(9) . . ? N1 C1 C2 104.89(9) . . ? C3 C2 C1 104.08(9) . . ? C2 C3 C4 102.69(9) . . ? N1 C4 C5 122.21(9) . . ? N1 C4 C3 101.09(8) . . ? C5 C4 C3 112.44(9) . . ? C6 C5 C10 118.84(10) . . ? C6 C5 C4 115.10(10) . . ? C10 C5 C4 125.80(9) . . ? C7 C6 C5 121.30(11) . . ? C8 C7 C6 119.94(10) . . ? C7 C8 C9 119.16(10) . . ? C8 C9 C10 121.84(11) . . ? C9 C10 C5 118.90(10) . . ? C9 C10 C11 119.48(9) . . ? C5 C10 C11 121.23(9) . . ? C10 C11 C12 112.97(9) . . ? C10 C11 C18 107.74(8) . . ? C12 C11 C18 114.82(9) . . ? C17 C12 C13 118.19(10) . . ? C17 C12 C11 122.98(10) . . ? C13 C12 C11 118.75(10) . . ? C14 C13 C12 121.24(11) . . ? C13 C14 C15 119.61(12) . . ? C16 C15 C14 120.02(11) . . ? C15 C16 C17 120.11(11) . . ? C12 C17 C16 120.82(11) . . ? C19 C18 C11 112.20(9) . . ? C20 C19 C18 109.51(9) . . ? O1 C20 N1 120.29(10) . . ? O1 C20 C19 120.38(10) . . ? N1 C20 C19 119.18(9) . . ? 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 C20 N1 C1 C2 172.15(10) . . . . ? C4 N1 C1 C2 -7.10(12) . . . . ? N1 C1 C2 C3 -19.06(12) . . . . ? C1 C2 C3 C4 37.36(12) . . . . ? C20 N1 C4 C5 -23.46(18) . . . . ? C1 N1 C4 C5 155.65(10) . . . . ? C20 N1 C4 C3 -149.13(11) . . . . ? C1 N1 C4 C3 29.98(11) . . . . ? C2 C3 C4 N1 -40.72(11) . . . . ? C2 C3 C4 C5 -172.68(9) . . . . ? N1 C4 C5 C6 143.48(10) . . . . ? C3 C4 C5 C6 -96.12(11) . . . . ? N1 C4 C5 C10 -42.54(16) . . . . ? C3 C4 C5 C10 77.86(13) . . . . ? C10 C5 C6 C7 -1.00(16) . . . . ? C4 C5 C6 C7 173.43(10) . . . . ? C5 C6 C7 C8 0.96(18) . . . . ? C6 C7 C8 C9 0.13(17) . . . . ? C7 C8 C9 C10 -1.19(17) . . . . ? C8 C9 C10 C5 1.14(16) . . . . ? C8 C9 C10 C11 174.06(10) . . . . ? C6 C5 C10 C9 -0.05(15) . . . . ? C4 C5 C10 C9 -173.82(10) . . . . ? C6 C5 C10 C11 -172.83(10) . . . . ? C4 C5 C10 C11 13.39(16) . . . . ? C9 C10 C11 C12 38.98(13) . . . . ? C5 C10 C11 C12 -148.27(10) . . . . ? C9 C10 C11 C18 -88.92(11) . . . . ? C5 C10 C11 C18 83.82(11) . . . . ? C10 C11 C12 C17 -130.06(10) . . . . ? C18 C11 C12 C17 -5.96(14) . . . . ? C10 C11 C12 C13 53.24(13) . . . . ? C18 C11 C12 C13 177.34(9) . . . . ? C17 C12 C13 C14 0.67(16) . . . . ? C11 C12 C13 C14 177.52(10) . . . . ? C12 C13 C14 C15 -0.84(17) . . . . ? C13 C14 C15 C16 -0.05(17) . . . . ? C14 C15 C16 C17 1.08(17) . . . . ? C13 C12 C17 C16 0.38(16) . . . . ? C11 C12 C17 C16 -176.33(10) . . . . ? C15 C16 C17 C12 -1.26(17) . . . . ? C10 C11 C18 C19 -56.51(11) . . . . ? C12 C11 C18 C19 176.66(8) . . . . ? C11 C18 C19 C20 -59.42(12) . . . . ? C1 N1 C20 O1 4.52(15) . . . . ? C4 N1 C20 O1 -176.43(10) . . . . ? C1 N1 C20 C19 -171.07(9) . . . . ? C4 N1 C20 C19 7.98(17) . . . . ? C18 C19 C20 O1 -90.62(12) . . . . ? C18 C19 C20 N1 84.97(12) . . . . ? _diffrn_measured_fraction_theta_max 0.956 _diffrn_reflns_theta_full 26.00 _diffrn_measured_fraction_theta_full 0.993 _refine_diff_density_max 0.402 _refine_diff_density_min -0.248 _refine_diff_density_rms 0.052 # Attachment 'dibenzoazocine12a.CIF' data_str0625 _database_code_depnum_ccdc_archive 'CCDC 703701' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C18 H17 N O' _chemical_formula_weight 263.33 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting triclinic _symmetry_space_group_name_H-M P-1 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 9.3106(8) _cell_length_b 10.4150(9) _cell_length_c 16.0747(14) _cell_angle_alpha 75.9490(10) _cell_angle_beta 88.8050(10) _cell_angle_gamma 63.5860(10) _cell_volume 1347.4(2) _cell_formula_units_Z 4 _cell_measurement_temperature 150(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 0.32 _exptl_crystal_size_mid 0.28 _exptl_crystal_size_min 0.18 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.298 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 560 _exptl_absorpt_coefficient_mu 0.080 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.9748 _exptl_absorpt_correction_T_max 0.9857 _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 150(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Bruker SMART APEX CCD diffractometer' _diffrn_measurement_method '\w rotation with narrow frames' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 11524 _diffrn_reflns_av_R_equivalents 0.0221 _diffrn_reflns_av_sigmaI/netI 0.0347 _diffrn_reflns_limit_h_min -12 _diffrn_reflns_limit_h_max 12 _diffrn_reflns_limit_k_min -13 _diffrn_reflns_limit_k_max 13 _diffrn_reflns_limit_l_min -20 _diffrn_reflns_limit_l_max 21 _diffrn_reflns_theta_min 2.63 _diffrn_reflns_theta_max 28.30 _reflns_number_total 6146 _reflns_number_gt 5332 _reflns_threshold_expression I>2\s(I) _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'Bruker SAINT' _computing_data_reduction 'Bruker SAINT' _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^)+(0.1039P)^2^+0.3159P] 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 6146 _refine_ls_number_parameters 361 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0583 _refine_ls_R_factor_gt 0.0520 _refine_ls_wR_factor_ref 0.1641 _refine_ls_wR_factor_gt 0.1554 _refine_ls_goodness_of_fit_ref 1.079 _refine_ls_restrained_S_all 1.079 _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 0.66111(14) 0.02856(12) 0.38139(7) 0.0302(3) Uani 1 1 d . . . N1 N 0.57306(14) 0.27406(13) 0.36836(7) 0.0209(3) Uani 1 1 d . . . C1 C 0.65060(17) 0.12871(16) 0.41254(9) 0.0212(3) Uani 1 1 d . . . C2 C 0.72424(16) 0.09704(15) 0.50151(9) 0.0201(3) Uani 1 1 d . . . C3 C 0.68653(17) 0.00969(16) 0.57001(10) 0.0254(3) Uani 1 1 d . . . H3A H 0.6136 -0.0272 0.5598 0.031 Uiso 1 1 calc R . . C4 C 0.75500(18) -0.02337(17) 0.65277(10) 0.0287(3) Uani 1 1 d . . . H4A H 0.7273 -0.0808 0.6996 0.034 Uiso 1 1 calc R . . C5 C 0.86449(18) 0.02776(17) 0.66714(10) 0.0281(3) Uani 1 1 d . . . H5A H 0.9126 0.0044 0.7238 0.034 Uiso 1 1 calc R . . C6 C 0.90364(17) 0.11270(16) 0.59896(10) 0.0248(3) Uani 1 1 d . . . H6A H 0.9791 0.1467 0.6094 0.030 Uiso 1 1 calc R . . C7 C 0.83413(16) 0.14923(14) 0.51509(9) 0.0200(3) Uani 1 1 d . . . C8 C 0.88637(16) 0.23277(15) 0.44064(10) 0.0230(3) Uani 1 1 d . . . H8A H 0.8805 0.1973 0.3896 0.028 Uiso 1 1 calc R . . H8B H 1.0010 0.2056 0.4547 0.028 Uiso 1 1 calc R . . C9 C 0.79284(17) 0.40105(15) 0.41542(9) 0.0214(3) Uani 1 1 d . . . C10 C 0.88279(19) 0.47965(17) 0.41021(10) 0.0292(3) Uani 1 1 d . . . H10A H 0.9961 0.4264 0.4247 0.035 Uiso 1 1 calc R . . C11 C 0.8103(2) 0.63389(18) 0.38432(11) 0.0336(4) Uani 1 1 d . . . H11A H 0.8735 0.6852 0.3818 0.040 Uiso 1 1 calc R . . C12 C 0.6472(2) 0.71136(17) 0.36249(10) 0.0310(3) Uani 1 1 d . . . H12A H 0.5968 0.8167 0.3440 0.037 Uiso 1 1 calc R . . C13 C 0.55555(18) 0.63524(16) 0.36752(9) 0.0253(3) Uani 1 1 d . . . H13A H 0.4425 0.6902 0.3523 0.030 Uiso 1 1 calc R . . C14 C 0.62478(17) 0.47992(15) 0.39440(8) 0.0202(3) Uani 1 1 d . . . C15 C 0.51912(16) 0.39993(15) 0.40848(9) 0.0206(3) Uani 1 1 d . . . H15A H 0.5196 0.3613 0.4719 0.025 Uiso 1 1 calc R . . C16 C 0.34350(18) 0.49126(18) 0.36841(11) 0.0296(3) Uani 1 1 d . . . H16A H 0.2738 0.4497 0.3987 0.036 Uiso 1 1 calc R . . H16B H 0.3009 0.5963 0.3699 0.036 Uiso 1 1 calc R . . C17 C 0.3549(2) 0.47700(19) 0.27606(11) 0.0341(4) Uani 1 1 d . . . H17A H 0.3939 0.5448 0.2406 0.041 Uiso 1 1 calc R . . H17B H 0.2491 0.4989 0.2491 0.041 Uiso 1 1 calc R . . C18 C 0.47629(19) 0.31503(17) 0.28632(10) 0.0278(3) Uani 1 1 d . . . H18A H 0.4209 0.2523 0.2889 0.033 Uiso 1 1 calc R . . H18B H 0.5446 0.3046 0.2379 0.033 Uiso 1 1 calc R . . O2 O 0.26310(14) 0.27668(13) 0.16205(7) 0.0314(3) Uani 1 1 d . . . N2 N 0.26531(14) 0.09978(13) 0.10284(7) 0.0204(3) Uani 1 1 d . . . C19 C 0.18996(18) 0.22815(15) 0.12639(8) 0.0214(3) Uani 1 1 d . . . C20 C 0.01085(17) 0.31141(15) 0.10590(9) 0.0207(3) Uani 1 1 d . . . C21 C -0.0842(2) 0.35448(16) 0.17204(10) 0.0276(3) Uani 1 1 d . . . H21A H -0.0352 0.3261 0.2291 0.033 Uiso 1 1 calc R . . C22 C -0.2490(2) 0.43820(18) 0.15446(12) 0.0339(4) Uani 1 1 d . . . H22A H -0.3139 0.4671 0.1994 0.041 Uiso 1 1 calc R . . C23 C -0.31948(19) 0.47985(17) 0.07104(12) 0.0338(4) Uani 1 1 d . . . H23A H -0.4331 0.5362 0.0589 0.041 Uiso 1 1 calc R . . C24 C -0.22452(18) 0.43956(16) 0.00491(11) 0.0276(3) Uani 1 1 d . . . H24A H -0.2740 0.4707 -0.0523 0.033 Uiso 1 1 calc R . . C25 C -0.05775(17) 0.35417(15) 0.02130(9) 0.0209(3) Uani 1 1 d . . . C26 C 0.04686(17) 0.32720(15) -0.05235(9) 0.0219(3) Uani 1 1 d . . . H26A H 0.1437 0.3372 -0.0382 0.026 Uiso 1 1 calc R . . H26B H -0.0134 0.4086 -0.1041 0.026 Uiso 1 1 calc R . . C27 C 0.10450(16) 0.18140(15) -0.07758(9) 0.0204(3) Uani 1 1 d . . . C28 C 0.09962(18) 0.19318(18) -0.16612(10) 0.0260(3) Uani 1 1 d . . . H28A H 0.0549 0.2891 -0.2053 0.031 Uiso 1 1 calc R . . C29 C 0.15800(19) 0.06930(19) -0.19865(10) 0.0289(3) Uani 1 1 d . . . H29A H 0.1560 0.0803 -0.2591 0.035 Uiso 1 1 calc R . . C30 C 0.21899(18) -0.07006(18) -0.14208(10) 0.0276(3) Uani 1 1 d . . . H30A H 0.2562 -0.1558 -0.1633 0.033 Uiso 1 1 calc R . . C31 C 0.22568(17) -0.08420(16) -0.05382(10) 0.0232(3) Uani 1 1 d . . . H31A H 0.2681 -0.1806 -0.0154 0.028 Uiso 1 1 calc R . . C32 C 0.17183(15) 0.03918(15) -0.01985(9) 0.0189(3) Uani 1 1 d . . . C33 C 0.18621(16) 0.01766(15) 0.07768(9) 0.0194(3) Uani 1 1 d . . . H33A H 0.0767 0.0508 0.0985 0.023 Uiso 1 1 calc R . . C34 C 0.29875(19) -0.14091(16) 0.13076(10) 0.0271(3) Uani 1 1 d . . . H34A H 0.2750 -0.1564 0.1917 0.033 Uiso 1 1 calc R . . H34B H 0.2889 -0.2159 0.1066 0.033 Uiso 1 1 calc R . . C35 C 0.46613(19) -0.14878(18) 0.12264(11) 0.0324(4) Uani 1 1 d . . . H35A H 0.5447 -0.2278 0.1702 0.039 Uiso 1 1 calc R . . H35B H 0.5052 -0.1676 0.0670 0.039 Uiso 1 1 calc R . . C36 C 0.43979(18) 0.00421(18) 0.12780(10) 0.0285(3) Uani 1 1 d . . . H36A H 0.4699 0.0020 0.1870 0.034 Uiso 1 1 calc R . . H36B H 0.5041 0.0400 0.0876 0.034 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 0.0390(6) 0.0271(5) 0.0308(6) -0.0117(5) 0.0021(5) -0.0182(5) N1 0.0232(6) 0.0226(6) 0.0178(5) -0.0068(5) -0.0002(4) -0.0103(5) C1 0.0213(6) 0.0230(7) 0.0227(7) -0.0074(5) 0.0044(5) -0.0124(5) C2 0.0186(6) 0.0183(6) 0.0213(7) -0.0059(5) 0.0020(5) -0.0062(5) C3 0.0223(7) 0.0232(7) 0.0283(7) -0.0028(6) 0.0025(6) -0.0102(6) C4 0.0262(7) 0.0283(7) 0.0226(7) -0.0014(6) 0.0047(6) -0.0073(6) C5 0.0254(7) 0.0268(7) 0.0223(7) -0.0072(6) -0.0020(6) -0.0028(6) C6 0.0208(7) 0.0208(6) 0.0291(7) -0.0092(6) -0.0020(5) -0.0046(5) C7 0.0172(6) 0.0156(6) 0.0242(7) -0.0062(5) 0.0021(5) -0.0044(5) C8 0.0174(6) 0.0202(6) 0.0290(7) -0.0046(5) 0.0031(5) -0.0075(5) C9 0.0243(7) 0.0210(6) 0.0194(6) -0.0048(5) 0.0024(5) -0.0108(6) C10 0.0286(8) 0.0280(8) 0.0321(8) -0.0027(6) -0.0007(6) -0.0161(6) C11 0.0449(10) 0.0285(8) 0.0342(8) -0.0047(6) 0.0029(7) -0.0244(7) C12 0.0434(9) 0.0212(7) 0.0279(8) -0.0051(6) 0.0051(7) -0.0149(7) C13 0.0286(7) 0.0205(7) 0.0209(7) -0.0049(5) 0.0018(6) -0.0062(6) C14 0.0244(7) 0.0198(6) 0.0162(6) -0.0060(5) 0.0026(5) -0.0092(5) C15 0.0199(6) 0.0221(6) 0.0189(6) -0.0082(5) 0.0028(5) -0.0073(5) C16 0.0198(7) 0.0293(8) 0.0359(8) -0.0097(6) 0.0009(6) -0.0072(6) C17 0.0299(8) 0.0341(8) 0.0313(8) -0.0047(7) -0.0090(6) -0.0098(7) C18 0.0341(8) 0.0297(8) 0.0209(7) -0.0059(6) -0.0044(6) -0.0158(6) O2 0.0397(6) 0.0327(6) 0.0276(6) -0.0066(5) -0.0073(5) -0.0216(5) N2 0.0183(6) 0.0215(6) 0.0211(6) -0.0038(5) -0.0007(4) -0.0096(5) C19 0.0284(7) 0.0215(6) 0.0146(6) -0.0015(5) -0.0013(5) -0.0131(6) C20 0.0259(7) 0.0168(6) 0.0222(7) -0.0060(5) 0.0026(5) -0.0116(5) C21 0.0393(9) 0.0209(7) 0.0253(7) -0.0081(6) 0.0085(6) -0.0151(6) C22 0.0355(9) 0.0262(7) 0.0455(10) -0.0163(7) 0.0190(7) -0.0158(7) C23 0.0232(7) 0.0226(7) 0.0562(11) -0.0134(7) 0.0069(7) -0.0093(6) C24 0.0263(7) 0.0188(6) 0.0375(8) -0.0072(6) -0.0039(6) -0.0098(6) C25 0.0239(7) 0.0159(6) 0.0252(7) -0.0063(5) 0.0007(5) -0.0105(5) C26 0.0272(7) 0.0184(6) 0.0202(6) -0.0032(5) -0.0005(5) -0.0112(5) C27 0.0209(6) 0.0205(6) 0.0222(7) -0.0060(5) 0.0015(5) -0.0113(5) C28 0.0266(7) 0.0302(7) 0.0220(7) -0.0063(6) -0.0004(5) -0.0138(6) C29 0.0284(7) 0.0406(9) 0.0252(7) -0.0161(7) 0.0042(6) -0.0183(7) C30 0.0241(7) 0.0319(8) 0.0363(8) -0.0215(7) 0.0071(6) -0.0146(6) C31 0.0197(6) 0.0231(7) 0.0305(7) -0.0103(6) 0.0042(5) -0.0114(5) C32 0.0159(6) 0.0207(6) 0.0235(7) -0.0077(5) 0.0033(5) -0.0104(5) C33 0.0192(6) 0.0176(6) 0.0211(6) -0.0042(5) 0.0029(5) -0.0085(5) C34 0.0315(8) 0.0194(7) 0.0238(7) -0.0027(5) 0.0039(6) -0.0072(6) C35 0.0239(7) 0.0292(8) 0.0291(8) -0.0040(6) -0.0012(6) -0.0007(6) C36 0.0193(7) 0.0348(8) 0.0258(7) -0.0041(6) -0.0015(5) -0.0093(6) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag O1 C1 1.2283(18) . ? N1 C1 1.3581(18) . ? N1 C18 1.4722(18) . ? N1 C15 1.4826(17) . ? C1 C2 1.4950(19) . ? C2 C3 1.395(2) . ? C2 C7 1.3970(19) . ? C3 C4 1.383(2) . ? C4 C5 1.389(2) . ? C5 C6 1.384(2) . ? C6 C7 1.396(2) . ? C7 C8 1.5075(19) . ? C8 C9 1.5186(19) . ? C9 C10 1.397(2) . ? C9 C14 1.4075(19) . ? C10 C11 1.390(2) . ? C11 C12 1.370(2) . ? C12 C13 1.389(2) . ? C13 C14 1.4013(19) . ? C14 C15 1.5302(19) . ? C15 C16 1.5349(19) . ? C16 C17 1.524(2) . ? C17 C18 1.525(2) . ? O2 C19 1.2292(17) . ? N2 C19 1.3502(18) . ? N2 C33 1.4760(17) . ? N2 C36 1.4783(18) . ? C19 C20 1.496(2) . ? C20 C25 1.395(2) . ? C20 C21 1.398(2) . ? C21 C22 1.380(2) . ? C22 C23 1.385(3) . ? C23 C24 1.391(2) . ? C24 C25 1.395(2) . ? C25 C26 1.516(2) . ? C26 C27 1.5242(19) . ? C27 C28 1.398(2) . ? C27 C32 1.4068(19) . ? C28 C29 1.388(2) . ? C29 C30 1.380(2) . ? C30 C31 1.390(2) . ? C31 C32 1.3989(19) . ? C32 C33 1.5288(19) . ? C33 C34 1.5385(19) . ? C34 C35 1.528(2) . ? C35 C36 1.524(2) . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C1 N1 C18 118.83(11) . . ? C1 N1 C15 124.43(11) . . ? C18 N1 C15 111.81(11) . . ? O1 C1 N1 122.29(13) . . ? O1 C1 C2 121.65(13) . . ? N1 C1 C2 116.05(12) . . ? C3 C2 C7 120.65(13) . . ? C3 C2 C1 118.96(13) . . ? C7 C2 C1 120.34(12) . . ? C4 C3 C2 120.16(14) . . ? C3 C4 C5 119.74(14) . . ? C6 C5 C4 120.08(14) . . ? C5 C6 C7 121.12(14) . . ? C6 C7 C2 118.22(13) . . ? C6 C7 C8 120.52(13) . . ? C2 C7 C8 121.10(12) . . ? C7 C8 C9 117.34(11) . . ? C10 C9 C14 119.24(13) . . ? C10 C9 C8 116.70(13) . . ? C14 C9 C8 124.01(12) . . ? C11 C10 C9 121.55(14) . . ? C12 C11 C10 119.56(15) . . ? C11 C12 C13 119.75(14) . . ? C12 C13 C14 122.03(14) . . ? C13 C14 C9 117.86(13) . . ? C13 C14 C15 120.81(13) . . ? C9 C14 C15 121.09(12) . . ? N1 C15 C14 113.75(11) . . ? N1 C15 C16 100.52(11) . . ? C14 C15 C16 116.50(12) . . ? C17 C16 C15 102.94(12) . . ? C16 C17 C18 103.40(13) . . ? N1 C18 C17 103.96(12) . . ? C19 N2 C33 125.62(11) . . ? C19 N2 C36 119.94(12) . . ? C33 N2 C36 111.65(11) . . ? O2 C19 N2 122.50(13) . . ? O2 C19 C20 120.83(13) . . ? N2 C19 C20 116.67(12) . . ? C25 C20 C21 121.07(13) . . ? C25 C20 C19 120.27(12) . . ? C21 C20 C19 118.48(13) . . ? C22 C21 C20 120.01(15) . . ? C21 C22 C23 119.70(15) . . ? C22 C23 C24 120.27(15) . . ? C23 C24 C25 120.99(15) . . ? C24 C25 C20 117.93(13) . . ? C24 C25 C26 120.55(13) . . ? C20 C25 C26 120.99(12) . . ? C25 C26 C27 119.76(11) . . ? C28 C27 C32 118.77(13) . . ? C28 C27 C26 115.68(12) . . ? C32 C27 C26 125.36(12) . . ? C29 C28 C27 122.12(14) . . ? C30 C29 C28 119.15(14) . . ? C29 C30 C31 119.61(13) . . ? C30 C31 C32 122.04(14) . . ? C31 C32 C27 118.25(13) . . ? C31 C32 C33 120.08(12) . . ? C27 C32 C33 121.66(12) . . ? N2 C33 C32 112.05(11) . . ? N2 C33 C34 100.17(11) . . ? C32 C33 C34 115.35(11) . . ? C35 C34 C33 103.13(12) . . ? C36 C35 C34 103.44(12) . . ? N2 C36 C35 104.27(12) . . ? 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 C18 N1 C1 O1 10.1(2) . . . . ? C15 N1 C1 O1 163.16(13) . . . . ? C18 N1 C1 C2 -170.43(12) . . . . ? C15 N1 C1 C2 -17.37(19) . . . . ? O1 C1 C2 C3 -53.47(19) . . . . ? N1 C1 C2 C3 127.05(14) . . . . ? O1 C1 C2 C7 123.94(15) . . . . ? N1 C1 C2 C7 -55.53(17) . . . . ? C7 C2 C3 C4 1.5(2) . . . . ? C1 C2 C3 C4 178.93(13) . . . . ? C2 C3 C4 C5 -1.5(2) . . . . ? C3 C4 C5 C6 0.6(2) . . . . ? C4 C5 C6 C7 0.3(2) . . . . ? C5 C6 C7 C2 -0.3(2) . . . . ? C5 C6 C7 C8 -175.77(13) . . . . ? C3 C2 C7 C6 -0.57(19) . . . . ? C1 C2 C7 C6 -177.94(12) . . . . ? C3 C2 C7 C8 174.82(13) . . . . ? C1 C2 C7 C8 -2.55(19) . . . . ? C6 C7 C8 C9 -91.74(16) . . . . ? C2 C7 C8 C9 92.98(16) . . . . ? C7 C8 C9 C10 127.13(14) . . . . ? C7 C8 C9 C14 -55.30(19) . . . . ? C14 C9 C10 C11 -0.3(2) . . . . ? C8 C9 C10 C11 177.34(15) . . . . ? C9 C10 C11 C12 -0.6(3) . . . . ? C10 C11 C12 C13 0.8(2) . . . . ? C11 C12 C13 C14 -0.1(2) . . . . ? C12 C13 C14 C9 -0.9(2) . . . . ? C12 C13 C14 C15 173.46(13) . . . . ? C10 C9 C14 C13 1.1(2) . . . . ? C8 C9 C14 C13 -176.42(13) . . . . ? C10 C9 C14 C15 -173.26(13) . . . . ? C8 C9 C14 C15 9.2(2) . . . . ? C1 N1 C15 C14 104.60(15) . . . . ? C18 N1 C15 C14 -100.70(13) . . . . ? C1 N1 C15 C16 -130.12(14) . . . . ? C18 N1 C15 C16 24.57(15) . . . . ? C13 C14 C15 N1 132.89(13) . . . . ? C9 C14 C15 N1 -52.93(17) . . . . ? C13 C14 C15 C16 16.65(19) . . . . ? C9 C14 C15 C16 -169.17(12) . . . . ? N1 C15 C16 C17 -39.06(14) . . . . ? C14 C15 C16 C17 84.32(15) . . . . ? C15 C16 C17 C18 40.26(16) . . . . ? C1 N1 C18 C17 156.15(13) . . . . ? C15 N1 C18 C17 -0.12(16) . . . . ? C16 C17 C18 N1 -24.84(16) . . . . ? C33 N2 C19 O2 165.81(13) . . . . ? C36 N2 C19 O2 6.4(2) . . . . ? C33 N2 C19 C20 -14.98(19) . . . . ? C36 N2 C19 C20 -174.42(12) . . . . ? O2 C19 C20 C25 122.72(15) . . . . ? N2 C19 C20 C25 -56.51(17) . . . . ? O2 C19 C20 C21 -52.58(19) . . . . ? N2 C19 C20 C21 128.19(14) . . . . ? C25 C20 C21 C22 1.3(2) . . . . ? C19 C20 C21 C22 176.56(13) . . . . ? C20 C21 C22 C23 -0.3(2) . . . . ? C21 C22 C23 C24 -1.0(2) . . . . ? C22 C23 C24 C25 1.4(2) . . . . ? C23 C24 C25 C20 -0.5(2) . . . . ? C23 C24 C25 C26 -172.23(13) . . . . ? C21 C20 C25 C24 -0.9(2) . . . . ? C19 C20 C25 C24 -176.06(12) . . . . ? C21 C20 C25 C26 170.85(12) . . . . ? C19 C20 C25 C26 -4.32(19) . . . . ? C24 C25 C26 C27 -99.39(16) . . . . ? C20 C25 C26 C27 89.09(16) . . . . ? C25 C26 C27 C28 138.53(14) . . . . ? C25 C26 C27 C32 -46.52(19) . . . . ? C32 C27 C28 C29 0.4(2) . . . . ? C26 C27 C28 C29 175.74(13) . . . . ? C27 C28 C29 C30 1.8(2) . . . . ? C28 C29 C30 C31 -2.0(2) . . . . ? C29 C30 C31 C32 0.2(2) . . . . ? C30 C31 C32 C27 2.0(2) . . . . ? C30 C31 C32 C33 -178.23(13) . . . . ? C28 C27 C32 C31 -2.28(19) . . . . ? C26 C27 C32 C31 -177.09(13) . . . . ? C28 C27 C32 C33 177.98(12) . . . . ? C26 C27 C32 C33 3.2(2) . . . . ? C19 N2 C33 C32 103.55(15) . . . . ? C36 N2 C33 C32 -95.56(13) . . . . ? C19 N2 C33 C34 -133.64(13) . . . . ? C36 N2 C33 C34 27.25(14) . . . . ? C31 C32 C33 N2 128.74(13) . . . . ? C27 C32 C33 N2 -51.53(16) . . . . ? C31 C32 C33 C34 14.99(18) . . . . ? C27 C32 C33 C34 -165.28(12) . . . . ? N2 C33 C34 C35 -39.95(13) . . . . ? C32 C33 C34 C35 80.52(14) . . . . ? C33 C34 C35 C36 39.06(15) . . . . ? C19 N2 C36 C35 158.52(13) . . . . ? C33 N2 C36 C35 -3.59(15) . . . . ? C34 C35 C36 N2 -22.10(15) . . . . ? _diffrn_measured_fraction_theta_max 0.918 _diffrn_reflns_theta_full 26.00 _diffrn_measured_fraction_theta_full 0.977 _refine_diff_density_max 0.476 _refine_diff_density_min -0.433 _refine_diff_density_rms 0.083