# Supplementary Material (ESI) for Chemical Communications # This journal is © The Royal Society of Chemistry 2005 data_global _journal_coden_Cambridge 182 _publ_contact_author_name A.G.Samuelson _publ_contact_author_address ; Department of Inorganic and Physical Chemistry Indian Institute of Science, Bangalore, India ; _publ_contact_author_email ashoka@ipc.iisc.ernet.in _publ_requested_journal 'Chemical Communications' _publ_section_title ; Insertion Mediated Catalytic Metathesis of Heterocumulenes. ; loop_ _publ_author_name _publ_author_address 'Rajshekhar Ghosh' ; Department of Inorganic and Physical Chemistry Indian Institute of Science, Bangalore, India ; A.G.Samuelson ; Department of Inorganic and Physical Chemistry Indian Institute of Science, Bangalore, India ; _publ_requested_category CO data_ghos3_m _database_code_depnum_ccdc_archive 'CCDC 252216' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C16 H18 N2 O' _chemical_formula_sum 'C16 H18 N2 O' _chemical_formula_weight 254.32 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 Triclinic _symmetry_space_group_name_H-M P-1 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 8.9335(18) _cell_length_b 9.5181(19) _cell_length_c 9.5609(19) _cell_angle_alpha 110.127(3) _cell_angle_beta 99.664(3) _cell_angle_gamma 101.080(3) _cell_volume 724.5(3) _cell_formula_units_Z 2 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used 484 _cell_measurement_theta_min 2.4 _cell_measurement_theta_max 25.31 _exptl_crystal_description Irregular _exptl_crystal_colour Colorless _exptl_crystal_size_max 0.43 _exptl_crystal_size_mid 0.36 _exptl_crystal_size_min 0.32 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.166 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 272 _exptl_absorpt_coefficient_mu 0.074 _exptl_absorpt_correction_type Empirical _exptl_absorpt_correction_T_min 0.71 _exptl_absorpt_correction_T_max 0.9702 _exptl_absorpt_process_details Empirical _exptl_special_details ; ? ; _diffrn_ambient_temperature 293(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'CCD Area Detector' _diffrn_measurement_method 'Phi & Omega Scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 7559 _diffrn_reflns_av_R_equivalents 0.0594 _diffrn_reflns_av_sigmaI/netI 0.0418 _diffrn_reflns_limit_h_min -10 _diffrn_reflns_limit_h_max 11 _diffrn_reflns_limit_k_min -11 _diffrn_reflns_limit_k_max 11 _diffrn_reflns_limit_l_min -11 _diffrn_reflns_limit_l_max 11 _diffrn_reflns_theta_min 2.35 _diffrn_reflns_theta_max 26.01 _reflns_number_total 2835 _reflns_number_gt 2250 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'BRUKER SMART' _computing_cell_refinement 'BRUKER SMART' _computing_data_reduction 'BRUKER SAINT' _computing_structure_solution 'BRUKER SHELXTL' _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^+0.0404P] 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 0.043(6) _refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^ _refine_ls_number_reflns 2835 _refine_ls_number_parameters 245 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0597 _refine_ls_R_factor_gt 0.0496 _refine_ls_wR_factor_ref 0.1371 _refine_ls_wR_factor_gt 0.1292 _refine_ls_goodness_of_fit_ref 1.063 _refine_ls_restrained_S_all 1.063 _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 O1 O 0.14730(12) 0.28266(11) 0.16058(11) 0.0614(3) Uani 1 1 d . . . N1 N 0.30574(15) 0.18441(14) 0.01925(15) 0.0614(4) Uani 1 1 d . . . N2 N 0.16763(15) 0.34933(14) -0.04539(14) 0.0622(3) Uani 1 1 d . . . C1 C 0.20440(15) 0.27640(15) 0.03784(15) 0.0515(3) Uani 1 1 d . . . C2 C 0.34288(16) 0.09777(14) 0.10897(14) 0.0505(3) Uani 1 1 d . . . C3 C 0.49738(18) 0.12207(18) 0.18189(18) 0.0621(4) Uani 1 1 d . . . C4 C 0.5361(2) 0.0331(2) 0.26276(19) 0.0729(5) Uani 1 1 d . . . C5 C 0.4219(2) -0.0810(2) 0.2693(2) 0.0776(5) Uani 1 1 d . . . C6 C 0.2670(2) -0.1053(2) 0.1966(2) 0.0790(5) Uani 1 1 d . . . C7 C 0.2275(2) -0.01655(18) 0.11648(18) 0.0646(4) Uani 1 1 d . . . C8 C 0.22697(16) 0.33098(17) -0.17702(15) 0.0553(4) Uani 1 1 d . . . C9 C 0.3415(2) 0.44976(19) -0.17871(19) 0.0667(4) Uani 1 1 d . . . C10 C 0.3950(2) 0.4356(2) -0.3089(2) 0.0803(5) Uani 1 1 d . . . C11 C 0.3330(2) 0.3035(3) -0.4403(2) 0.0834(6) Uani 1 1 d . . . C12 C 0.2193(2) 0.1852(3) -0.4398(2) 0.0867(6) Uani 1 1 d . . . C13 C 0.1658(2) 0.1972(2) -0.30964(19) 0.0740(5) Uani 1 1 d . . . C14 C 0.05091(19) 0.38980(19) 0.20711(19) 0.0666(4) Uani 1 1 d . . . C15 C 0.1578(3) 0.5475(2) 0.3073(3) 0.0896(6) Uani 1 1 d . . . C16 C -0.0526(2) 0.3225(3) 0.2896(2) 0.0822(5) Uani 1 1 d . . . H1 H 0.3555(18) 0.1892(17) -0.0484(18) 0.063(4) Uiso 1 1 d . . . H3 H 0.577(2) 0.198(2) 0.1733(19) 0.080(5) Uiso 1 1 d . . . H4 H 0.646(2) 0.057(2) 0.315(2) 0.085(5) Uiso 1 1 d . . . H5 H 0.446(2) -0.141(2) 0.326(2) 0.091(5) Uiso 1 1 d . . . H6 H 0.185(2) -0.185(2) 0.202(2) 0.089(5) Uiso 1 1 d . . . H7 H 0.119(2) -0.0353(19) 0.0652(18) 0.075(5) Uiso 1 1 d . . . H9 H 0.384(2) 0.546(2) -0.085(2) 0.087(5) Uiso 1 1 d . . . H10 H 0.473(2) 0.519(2) -0.312(2) 0.100(6) Uiso 1 1 d . . . H11 H 0.370(2) 0.297(2) -0.529(2) 0.099(6) Uiso 1 1 d . . . H12 H 0.176(3) 0.090(3) -0.524(3) 0.117(7) Uiso 1 1 d . . . H13 H 0.089(2) 0.114(2) -0.311(2) 0.091(6) Uiso 1 1 d . . . H14 H -0.0082(18) 0.3942(17) 0.1151(18) 0.066(4) Uiso 1 1 d . . . H16A H -0.122(3) 0.213(3) 0.222(3) 0.112(7) Uiso 1 1 d . . . H16B H 0.013(2) 0.316(2) 0.381(2) 0.098(6) Uiso 1 1 d . . . H16C H -0.122(3) 0.391(3) 0.322(2) 0.109(6) Uiso 1 1 d . . . H15A H 0.226(3) 0.585(2) 0.248(2) 0.104(6) Uiso 1 1 d . . . H15B H 0.223(3) 0.542(3) 0.400(3) 0.116(8) Uiso 1 1 d . . . H15C H 0.093(3) 0.623(3) 0.336(2) 0.106(6) Uiso 1 1 d . . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 O1 0.0749(7) 0.0657(6) 0.0652(6) 0.0306(5) 0.0390(5) 0.0389(5) N1 0.0767(8) 0.0679(8) 0.0645(8) 0.0340(6) 0.0408(6) 0.0398(6) N2 0.0737(8) 0.0684(8) 0.0618(7) 0.0304(6) 0.0305(6) 0.0365(6) C1 0.0552(8) 0.0495(7) 0.0531(7) 0.0174(6) 0.0225(6) 0.0185(6) C2 0.0615(8) 0.0462(7) 0.0480(7) 0.0125(5) 0.0249(6) 0.0253(6) C3 0.0595(9) 0.0566(9) 0.0720(9) 0.0199(7) 0.0247(7) 0.0223(7) C4 0.0699(10) 0.0749(11) 0.0737(10) 0.0228(8) 0.0147(8) 0.0339(9) C5 0.0994(14) 0.0768(11) 0.0778(11) 0.0404(9) 0.0300(9) 0.0453(11) C6 0.0831(12) 0.0696(11) 0.0995(13) 0.0458(10) 0.0311(10) 0.0231(9) C7 0.0626(9) 0.0583(9) 0.0720(10) 0.0237(7) 0.0162(7) 0.0181(7) C8 0.0592(8) 0.0631(8) 0.0531(8) 0.0251(6) 0.0172(6) 0.0304(7) C9 0.0818(11) 0.0608(9) 0.0618(9) 0.0237(7) 0.0237(8) 0.0241(8) C10 0.0954(13) 0.0857(13) 0.0838(13) 0.0459(11) 0.0435(10) 0.0359(11) C11 0.1016(14) 0.1125(16) 0.0627(11) 0.0424(11) 0.0388(10) 0.0575(13) C12 0.0945(14) 0.0973(14) 0.0521(10) 0.0082(10) 0.0124(9) 0.0343(11) C13 0.0706(11) 0.0726(11) 0.0658(10) 0.0143(8) 0.0152(8) 0.0156(9) C14 0.0750(10) 0.0805(11) 0.0661(9) 0.0315(8) 0.0358(8) 0.0483(9) C15 0.1155(16) 0.0665(12) 0.1087(17) 0.0350(11) 0.0595(14) 0.0448(11) C16 0.0693(11) 0.1029(15) 0.0810(12) 0.0289(11) 0.0389(9) 0.0342(11) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag O1 C1 1.3436(15) . ? O1 C14 1.4606(16) . ? N1 C1 1.3673(17) . ? N1 C2 1.4220(17) . ? N2 C1 1.2661(17) . ? N2 C8 1.4155(17) . ? C2 C3 1.374(2) . ? C2 C7 1.378(2) . ? C3 C4 1.381(2) . ? C4 C5 1.366(3) . ? C5 C6 1.376(3) . ? C6 C7 1.376(2) . ? C8 C9 1.378(2) . ? C8 C13 1.384(2) . ? C9 C10 1.379(2) . ? C10 C11 1.371(3) . ? C11 C12 1.366(3) . ? C12 C13 1.383(3) . ? C14 C15 1.495(3) . ? C14 C16 1.500(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 O1 C14 117.91(10) . . ? C1 N1 C2 126.51(11) . . ? C1 N2 C8 119.36(11) . . ? N2 C1 O1 122.76(12) . . ? N2 C1 N1 126.35(12) . . ? O1 C1 N1 110.89(11) . . ? C3 C2 C7 119.42(14) . . ? C3 C2 N1 119.47(13) . . ? C7 C2 N1 121.00(13) . . ? C2 C3 C4 120.09(15) . . ? C5 C4 C3 120.50(16) . . ? C4 C5 C6 119.50(16) . . ? C5 C6 C7 120.31(17) . . ? C6 C7 C2 120.18(16) . . ? C9 C8 C13 118.36(15) . . ? C9 C8 N2 120.53(13) . . ? C13 C8 N2 121.02(15) . . ? C8 C9 C10 120.95(17) . . ? C11 C10 C9 120.43(18) . . ? C12 C11 C10 119.04(17) . . ? C11 C12 C13 121.12(18) . . ? C12 C13 C8 120.08(19) . . ? O1 C14 C15 108.62(14) . . ? O1 C14 C16 105.18(13) . . ? C15 C14 C16 113.06(16) . . ? _diffrn_measured_fraction_theta_max 0.992 _diffrn_reflns_theta_full 26.01 _diffrn_measured_fraction_theta_full 0.992 _refine_diff_density_max 0.174 _refine_diff_density_min -0.195 _refine_diff_density_rms 0.038 data_raj2_a _database_code_depnum_ccdc_archive 'CCDC 252217' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C23 H23 N3 O2' _chemical_formula_sum 'C23 H23 N3 O2' _chemical_formula_weight 373.44 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 9.505(5) _cell_length_b 10.689(6) _cell_length_c 10.748(6) _cell_angle_alpha 81.385(9) _cell_angle_beta 71.862(9) _cell_angle_gamma 88.352(9) _cell_volume 1025.9(10) _cell_formula_units_Z 2 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min 1.93 _cell_measurement_theta_max 26.10 _exptl_crystal_description Rectangular _exptl_crystal_colour 'Pale yellow' _exptl_crystal_size_max 0.40 _exptl_crystal_size_mid 0.32 _exptl_crystal_size_min 0.28 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.209 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 396 _exptl_absorpt_coefficient_mu 0.078 _exptl_absorpt_correction_type empirical _exptl_absorpt_correction_T_min 0.7814 _exptl_absorpt_correction_T_max 1 _exptl_absorpt_process_details 'Psi scans' _exptl_special_details ; ? ; _diffrn_ambient_temperature 293(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'CCD area detector' _diffrn_measurement_method 'phi and omega scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 10794 _diffrn_reflns_av_R_equivalents 0.0563 _diffrn_reflns_av_sigmaI/netI 0.0430 _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 -13 _diffrn_reflns_limit_l_max 13 _diffrn_reflns_theta_min 1.93 _diffrn_reflns_theta_max 26.10 _reflns_number_total 4038 _reflns_number_gt 3074 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'Bruker SMART' _computing_data_reduction 'Bruker SAINT' _computing_structure_solution 'Bruker SHELXTL' _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^)+(0.0550P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment mixed _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 4038 _refine_ls_number_parameters 345 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0544 _refine_ls_R_factor_gt 0.0398 _refine_ls_wR_factor_ref 0.1053 _refine_ls_wR_factor_gt 0.0982 _refine_ls_goodness_of_fit_ref 1.016 _refine_ls_restrained_S_all 1.016 _refine_ls_shift/su_max 0.002 _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 0.49264(10) 0.41946(8) 0.15688(8) 0.0575(2) Uani 1 1 d . . . O2 O 0.56626(9) 0.29527(7) -0.00387(8) 0.0544(2) Uani 1 1 d . . . N1 N 0.34548(13) 0.32843(10) -0.14149(10) 0.0516(3) Uani 1 1 d . . . N2 N 0.24996(12) 0.14642(9) 0.00774(10) 0.0540(3) Uani 1 1 d . . . N3 N 0.32614(11) 0.32758(8) 0.08052(9) 0.0466(2) Uani 1 1 d . . . C1 C 0.30641(13) 0.25721(11) -0.01853(11) 0.0467(3) Uani 1 1 d . . . C2 C 0.37284(14) 0.28232(11) -0.26352(11) 0.0491(3) Uani 1 1 d . . . C3 C 0.47854(18) 0.34630(14) -0.37312(13) 0.0644(4) Uani 1 1 d . . . C4 C 0.5113(2) 0.30451(17) -0.49446(15) 0.0764(4) Uani 1 1 d . . . C5 C 0.44192(18) 0.19952(16) -0.50842(15) 0.0715(4) Uani 1 1 d . . . C6 C 0.33622(18) 0.13661(17) -0.40059(15) 0.0708(4) Uani 1 1 d . . . C7 C 0.29921(16) 0.17778(14) -0.27797(14) 0.0615(4) Uani 1 1 d . . . C8 C 0.23000(14) 0.07546(10) 0.13472(11) 0.0476(3) Uani 1 1 d . . . C9 C 0.08909(16) 0.03535(13) 0.21609(14) 0.0601(3) Uani 1 1 d . . . C10 C 0.07046(19) -0.03701(14) 0.33789(15) 0.0675(4) Uani 1 1 d . . . C11 C 0.19043(18) -0.07248(14) 0.37960(15) 0.0645(4) Uani 1 1 d . . . C12 C 0.33013(17) -0.03621(12) 0.29884(14) 0.0606(4) Uani 1 1 d . . . C13 C 0.35071(16) 0.03698(11) 0.17693(13) 0.0536(3) Uani 1 1 d . . . C14 C 0.19416(14) 0.35423(10) 0.18230(11) 0.0484(3) Uani 1 1 d . . . C15 C 0.06920(15) 0.39249(12) 0.14705(15) 0.0601(3) Uani 1 1 d . . . C16 C -0.05963(19) 0.41571(16) 0.24358(19) 0.0787(5) Uani 1 1 d . . . C17 C -0.0654(2) 0.40120(18) 0.3738(2) 0.0889(5) Uani 1 1 d . . . C18 C 0.0577(2) 0.36213(17) 0.40878(17) 0.0814(5) Uani 1 1 d . . . C19 C 0.18785(18) 0.33739(13) 0.31394(13) 0.0636(4) Uani 1 1 d . . . C20 C 0.46604(14) 0.35325(10) 0.08445(11) 0.0462(3) Uani 1 1 d . . . C21 C 0.72301(15) 0.30881(13) -0.01498(15) 0.0611(4) Uani 1 1 d . . . C22 C 0.8057(2) 0.3033(2) -0.1572(2) 0.0865(6) Uani 1 1 d . . . C23 C 0.7590(3) 0.2043(2) 0.0802(3) 0.0949(6) Uani 1 1 d . . . H1 H 0.3848(14) 0.3977(13) -0.1457(12) 0.051(4) Uiso 1 1 d . . . H3 H 0.5278(15) 0.4223(13) -0.3620(12) 0.062(4) Uiso 1 1 d . . . H4 H 0.580(2) 0.3514(17) -0.5678(17) 0.101(6) Uiso 1 1 d . . . H5 H 0.4643(17) 0.1645(14) -0.5901(16) 0.085(5) Uiso 1 1 d . . . H6 H 0.2862(19) 0.0615(16) -0.4047(14) 0.085(5) Uiso 1 1 d . . . H7 H 0.2263(16) 0.1358(13) -0.2054(13) 0.064(4) Uiso 1 1 d . . . H9 H 0.0063(18) 0.0558(14) 0.1838(14) 0.080(4) Uiso 1 1 d . . . H10 H -0.0259(19) -0.0648(14) 0.3923(14) 0.077(4) Uiso 1 1 d . . . H11 H 0.1770(17) -0.1233(14) 0.4648(15) 0.079(4) Uiso 1 1 d . . . H12 H 0.4193(17) -0.0627(13) 0.3250(13) 0.078(4) Uiso 1 1 d . . . H13 H 0.4477(17) 0.0605(12) 0.1190(13) 0.061(4) Uiso 1 1 d . . . H15 H 0.0748(16) 0.4028(14) 0.0536(16) 0.078(4) Uiso 1 1 d . . . H16 H -0.146(2) 0.4404(16) 0.2163(16) 0.093(5) Uiso 1 1 d . . . H17 H -0.157(2) 0.4188(18) 0.4437(19) 0.125(7) Uiso 1 1 d . . . H18 H 0.0583(19) 0.3513(16) 0.4952(17) 0.096(6) Uiso 1 1 d . . . H19 H 0.2761(17) 0.3116(13) 0.3367(13) 0.069(4) Uiso 1 1 d . . . H21 H 0.7366(13) 0.3918(12) 0.0083(11) 0.055(3) Uiso 1 1 d . . . H22A H 0.913(3) 0.3142(18) -0.1731(18) 0.116(7) Uiso 1 1 d . . . H22B H 0.7852(19) 0.2267(18) -0.1807(15) 0.092(5) Uiso 1 1 d . . . H22C H 0.779(2) 0.377(2) -0.2162(19) 0.123(8) Uiso 1 1 d . . . H23A H 0.7386(19) 0.1167(18) 0.0582(16) 0.099(6) Uiso 1 1 d . . . H23B H 0.701(3) 0.213(2) 0.172(2) 0.124(8) Uiso 1 1 d . . . H23C H 0.853(3) 0.2144(19) 0.0737(19) 0.119(7) Uiso 1 1 d . . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 O1 0.0694(6) 0.0524(5) 0.0573(5) -0.0160(4) -0.0249(4) -0.0078(4) O2 0.0535(5) 0.0514(5) 0.0644(5) -0.0193(4) -0.0221(4) 0.0011(4) N1 0.0662(7) 0.0437(6) 0.0496(6) -0.0046(5) -0.0249(5) -0.0053(5) N2 0.0696(7) 0.0455(6) 0.0510(6) -0.0059(5) -0.0246(5) -0.0066(5) N3 0.0531(6) 0.0425(5) 0.0479(6) -0.0105(4) -0.0192(5) -0.0003(4) C1 0.0530(7) 0.0443(6) 0.0479(7) -0.0089(5) -0.0223(6) 0.0012(5) C2 0.0555(7) 0.0514(7) 0.0474(7) -0.0063(5) -0.0269(6) 0.0055(6) C3 0.0820(10) 0.0582(8) 0.0540(8) 0.0016(6) -0.0262(7) -0.0082(7) C4 0.0917(12) 0.0845(11) 0.0487(8) 0.0008(8) -0.0204(8) -0.0024(9) C5 0.0821(11) 0.0897(11) 0.0526(9) -0.0180(8) -0.0327(8) 0.0116(9) C6 0.0738(10) 0.0848(11) 0.0695(10) -0.0252(8) -0.0384(8) -0.0011(9) C7 0.0578(8) 0.0776(9) 0.0563(8) -0.0154(7) -0.0246(7) -0.0089(7) C8 0.0573(8) 0.0383(6) 0.0504(7) -0.0106(5) -0.0192(6) -0.0024(5) C9 0.0535(8) 0.0575(8) 0.0702(9) -0.0109(7) -0.0204(7) 0.0051(6) C10 0.0614(9) 0.0669(9) 0.0612(9) -0.0058(7) -0.0020(8) -0.0011(7) C11 0.0802(11) 0.0576(8) 0.0514(8) -0.0034(7) -0.0165(8) -0.0005(7) C12 0.0712(10) 0.0519(7) 0.0662(9) -0.0074(7) -0.0329(8) 0.0026(7) C13 0.0519(8) 0.0476(7) 0.0603(8) -0.0073(6) -0.0159(7) -0.0052(6) C14 0.0573(8) 0.0387(6) 0.0489(7) -0.0077(5) -0.0151(6) -0.0021(5) C15 0.0587(9) 0.0575(8) 0.0659(9) -0.0116(7) -0.0209(7) -0.0001(6) C16 0.0575(10) 0.0850(11) 0.0938(13) -0.0257(9) -0.0178(9) 0.0019(8) C17 0.0662(11) 0.0984(13) 0.0913(13) -0.0357(10) 0.0018(10) -0.0072(9) C18 0.0911(13) 0.0898(11) 0.0536(9) -0.0153(8) -0.0050(9) -0.0138(9) C19 0.0731(10) 0.0632(8) 0.0528(8) -0.0065(6) -0.0182(7) 0.0005(7) C20 0.0581(8) 0.0368(6) 0.0460(6) -0.0049(5) -0.0195(6) -0.0011(5) C21 0.0526(8) 0.0499(7) 0.0848(10) -0.0199(7) -0.0220(7) -0.0041(6) C22 0.0743(12) 0.0732(11) 0.1022(14) -0.0359(11) -0.0018(10) -0.0095(9) C23 0.0869(14) 0.0807(13) 0.137(2) -0.0087(12) -0.0672(15) 0.0072(10) _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 C20 1.2119(13) . ? O2 C20 1.3312(15) . ? O2 C21 1.4668(17) . ? N1 C1 1.3687(16) . ? N1 C2 1.4159(16) . ? N2 C1 1.2697(15) . ? N2 C8 1.4180(16) . ? N3 C20 1.3801(17) . ? N3 C14 1.4388(16) . ? N3 C1 1.4514(15) . ? C2 C3 1.3878(19) . ? C2 C7 1.3883(18) . ? C3 C4 1.382(2) . ? C4 C5 1.368(2) . ? C5 C6 1.373(2) . ? C6 C7 1.389(2) . ? C8 C13 1.3901(19) . ? C8 C9 1.3907(19) . ? C9 C10 1.380(2) . ? C10 C11 1.374(2) . ? C11 C12 1.370(2) . ? C12 C13 1.3817(19) . ? C14 C19 1.3817(19) . ? C14 C15 1.3883(19) . ? C15 C16 1.381(2) . ? C16 C17 1.369(3) . ? C17 C18 1.372(3) . ? C18 C19 1.384(2) . ? C21 C22 1.495(2) . ? C21 C23 1.505(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 C20 O2 C21 118.61(10) . . ? C1 N1 C2 126.20(11) . . ? C1 N2 C8 119.43(10) . . ? C20 N3 C14 122.25(10) . . ? C20 N3 C1 120.70(10) . . ? C14 N3 C1 116.60(10) . . ? N2 C1 N1 124.26(10) . . ? N2 C1 N3 123.87(10) . . ? N1 C1 N3 111.69(10) . . ? C3 C2 C7 119.24(13) . . ? C3 C2 N1 117.49(12) . . ? C7 C2 N1 123.27(12) . . ? C4 C3 C2 120.03(15) . . ? C5 C4 C3 120.94(16) . . ? C4 C5 C6 119.26(15) . . ? C5 C6 C7 121.03(16) . . ? C2 C7 C6 119.46(15) . . ? C13 C8 C9 118.48(12) . . ? C13 C8 N2 121.01(11) . . ? C9 C8 N2 120.36(11) . . ? C10 C9 C8 120.23(14) . . ? C11 C10 C9 120.73(15) . . ? C12 C11 C10 119.56(14) . . ? C11 C12 C13 120.47(14) . . ? C12 C13 C8 120.49(13) . . ? C19 C14 C15 119.76(13) . . ? C19 C14 N3 121.40(12) . . ? C15 C14 N3 118.79(11) . . ? C16 C15 C14 119.72(15) . . ? C17 C16 C15 120.61(17) . . ? C16 C17 C18 119.66(17) . . ? C17 C18 C19 120.81(17) . . ? C14 C19 C18 119.42(16) . . ? O1 C20 O2 125.58(12) . . ? O1 C20 N3 124.80(11) . . ? O2 C20 N3 109.62(10) . . ? O2 C21 C22 105.20(13) . . ? O2 C21 C23 108.04(13) . . ? C22 C21 C23 114.13(17) . . ? _diffrn_measured_fraction_theta_max 0.990 _diffrn_reflns_theta_full 26.10 _diffrn_measured_fraction_theta_full 0.990 _refine_diff_density_max 0.158 _refine_diff_density_min -0.192 _refine_diff_density_rms 0.034