Supplementary Material (ESI) for Chemical Communications This journal is © The Royal Society of Chemistry 2002 data_global _journal_coden_Cambridge 182 loop_ _publ_author_name 'Ian Fleming' 'Marina Buswell' _publ_contact_author_name 'Prof Ian Fleming' _publ_contact_author_address ; Chemistry University of Cambridge Department of Chemistry Lensfield Road Cambridge CB2 1EW UNITED KINGDOM ; _publ_contact_author_email IF10000@CAM.AC.UK _publ_requested_journal 'Chemical Communications' _publ_section_title ; The reaction of phenyldimethylsilyllithium with N-phenylpyrrolidone ; data_if9902 _database_code_CSD 199968 _audit_creation_method SHELXL _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_formula_moiety ? _chemical_formula_structural ? _chemical_formula_analytical ? _chemical_formula_sum 'C20 H22 N2' _chemical_formula_weight 290.40 _chemical_melting_point ? _chemical_compound_source ? 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' _symmetry_cell_setting Orthorhombic _symmetry_space_group_name_H-M Fdd2 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, z' 'x+1/4, -y+1/4, z+1/4' '-x+1/4, y+1/4, z+1/4' 'x, y+1/2, z+1/2' '-x, -y+1/2, z+1/2' 'x+1/4, -y+3/4, z+3/4' '-x+1/4, y+3/4, z+3/4' 'x+1/2, y, z+1/2' '-x+1/2, -y, z+1/2' 'x+3/4, -y+1/4, z+3/4' '-x+3/4, y+1/4, z+3/4' 'x+1/2, y+1/2, z' '-x+1/2, -y+1/2, z' 'x+3/4, -y+3/4, z+1/4' '-x+3/4, y+3/4, z+1/4' _cell_length_a 24.888(5) _cell_length_b 43.375(9) _cell_length_c 5.6650(10) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 6115.5(21) _cell_formula_units_Z 16 _cell_measurement_temperature 180(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description ? _exptl_crystal_colour colourless _exptl_crystal_size_max 0.16 _exptl_crystal_size_mid 0.09 _exptl_crystal_size_min 0.05 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.262 _exptl_crystal_density_method ? _exptl_crystal_F_000 2496 _exptl_absorpt_coefficient_mu 0.074 _exptl_absorpt_correction_type ? _exptl_absorpt_correction_T_min ? _exptl_absorpt_correction_T_max ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 180(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 NoniusKappa _diffrn_measurement_method ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 8482 _diffrn_reflns_av_R_equivalents 0.1407 _diffrn_reflns_av_sigmaI/netI 0.1254 _diffrn_reflns_limit_h_min -29 _diffrn_reflns_limit_h_max 29 _diffrn_reflns_limit_k_min -51 _diffrn_reflns_limit_k_max 49 _diffrn_reflns_limit_l_min -6 _diffrn_reflns_limit_l_max 6 _diffrn_reflns_theta_min 1.88 _diffrn_reflns_theta_max 25.24 _reflns_number_total 2600 _reflns_number_observed 1638 _reflns_observed_criterion >2sigma(I) _computing_data_collection ? _computing_cell_refinement ? _computing_data_reduction ? _computing_structure_solution 'SHELXS-86 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-93 (Sheldrick, 1993)' _computing_molecular_graphics ? _computing_publication_material ? _refine_special_details ; Refinement on F^2^ for ALL reflections except for 6 with very negative F^2^ or flagged by the user for potential systematic errors. Weighted R-factors wR and all goodnesses 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 observed criterion of F^2^ > 2sigma(F^2^) is used only for calculating _R_factor_obs 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 w=1/[\s^2^(Fo^2^)+(0.0244P)^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 ? _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881' _refine_ls_abs_structure_Flack 1.91(473) _refine_ls_number_reflns 2594 _refine_ls_number_parameters 199 _refine_ls_number_restraints 1 _refine_ls_R_factor_all 0.1165 _refine_ls_R_factor_obs 0.0531 _refine_ls_wR_factor_all 0.2587 _refine_ls_wR_factor_obs 0.0929 _refine_ls_goodness_of_fit_all 1.004 _refine_ls_goodness_of_fit_obs 1.107 _refine_ls_restrained_S_all 2.394 _refine_ls_restrained_S_obs 1.106 _refine_ls_shift/esd_max -0.001 _refine_ls_shift/esd_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_thermal_displace_type _atom_site_occupancy _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_group N1 N 0.32631(8) 0.10981(5) 0.1597(5) 0.0377(6) Uani 1 d . . N2 N 0.33743(10) 0.02988(5) 0.5164(5) 0.0510(8) Uani 1 d . . C1 C 0.32131(11) 0.07611(5) 0.1508(6) 0.0366(8) Uani 1 d . . H1 H 0.31438(11) 0.06917(5) -0.0148(6) 0.044 Uiso 1 calc R . C2 C 0.27686(11) 0.06440(6) 0.3154(6) 0.0355(8) Uani 1 d . . C3 C 0.22532(11) 0.07655(6) 0.2964(6) 0.0395(8) Uani 1 d . . H3 H 0.21807(11) 0.09101(6) 0.1746(6) 0.047 Uiso 1 calc R . C4 C 0.18419(12) 0.06833(7) 0.4486(7) 0.0506(10) Uani 1 d . . H4 H 0.14960(12) 0.07739(7) 0.4335(7) 0.061 Uiso 1 calc R . C5 C 0.19408(13) 0.04709(6) 0.6200(7) 0.0520(10) Uani 1 d . . H5 H 0.16614(13) 0.04139(6) 0.7256(7) 0.062 Uiso 1 calc R . C6 C 0.24436(14) 0.03366(6) 0.6426(7) 0.0503(9) Uani 1 d . . H6 H 0.25057(14) 0.01873(6) 0.7621(7) 0.060 Uiso 1 calc R . C7 C 0.28621(12) 0.04213(6) 0.4887(6) 0.0393(8) Uani 1 d . . C8 C 0.34851(13) 0.00355(7) 0.6666(7) 0.0570(10) Uani 1 d . . H8A H 0.32511(13) -0.01410(7) 0.6253(7) 0.068 Uiso 1 calc R . H8B H 0.34309(13) 0.00880(7) 0.8350(7) 0.068 Uiso 1 calc R . C9 C 0.40740(14) -0.00382(8) 0.6164(8) 0.0737(13) Uani 1 d . . H9A H 0.42874(14) -0.00275(8) 0.7637(8) 0.088 Uiso 1 calc R . H9B H 0.41089(14) -0.02481(8) 0.5494(8) 0.088 Uiso 1 calc R . C10 C 0.42709(13) 0.02020(7) 0.4397(7) 0.0605(11) Uani 1 d . . H10A H 0.44706(13) 0.03688(7) 0.5206(7) 0.073 Uiso 1 calc R . H10B H 0.45077(13) 0.01067(7) 0.3197(7) 0.073 Uiso 1 calc R . C11 C 0.37599(12) 0.03259(6) 0.3268(7) 0.0459(9) Uani 1 d . . H11 H 0.36511(12) 0.01842(6) 0.1960(7) 0.055 Uiso 1 calc R . C12 C 0.37742(11) 0.06533(6) 0.2326(6) 0.0418(9) Uani 1 d . . H12 H 0.40276(11) 0.06627(6) 0.0958(6) 0.050 Uiso 1 calc R . C13 C 0.39343(12) 0.08988(6) 0.4131(7) 0.0492(9) Uani 1 d . . H13A H 0.37804(12) 0.08516(6) 0.5702(7) 0.059 Uiso 1 calc R . H13B H 0.43300(12) 0.09128(6) 0.4273(7) 0.059 Uiso 1 calc R . C14 C 0.37024(11) 0.11955(6) 0.3153(7) 0.0458(9) Uani 1 d . . H14A H 0.35655(11) 0.13280(6) 0.4443(7) 0.055 Uiso 1 calc R . H14B H 0.39780(11) 0.13112(6) 0.2257(7) 0.055 Uiso 1 calc R . C15 C 0.30320(11) 0.13033(6) 0.0034(6) 0.0344(7) Uani 1 d . . C16 C 0.27051(11) 0.12092(6) -0.1853(6) 0.0415(8) Uani 1 d . . H16 H 0.26248(11) 0.09968(6) -0.2056(6) 0.050 Uiso 1 calc R . C17 C 0.24998(12) 0.14230(7) -0.3412(7) 0.0488(9) Uani 1 d . . H17 H 0.22809(12) 0.13540(7) -0.4680(7) 0.059 Uiso 1 calc R . C18 C 0.26023(13) 0.17324(7) -0.3186(7) 0.0519(9) Uani 1 d . . H18 H 0.24648(13) 0.18766(7) -0.4295(7) 0.062 Uiso 1 calc R . C19 C 0.29110(12) 0.18275(7) -0.1302(7) 0.0490(9) Uani 1 d . . H19 H 0.29814(12) 0.20412(7) -0.1099(7) 0.059 Uiso 1 calc R . C20 C 0.31204(11) 0.16195(6) 0.0297(6) 0.0404(8) Uani 1 d . . H20 H 0.33271(11) 0.16923(6) 0.1593(6) 0.048 Uiso 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 0.0359(13) 0.0339(13) 0.043(2) 0.0023(12) -0.0068(13) -0.0079(11) N2 0.052(2) 0.052(2) 0.049(2) 0.0174(15) -0.005(2) 0.0087(13) C1 0.037(2) 0.035(2) 0.038(2) 0.002(2) 0.000(2) -0.0031(12) C2 0.039(2) 0.0314(15) 0.036(2) -0.0034(15) -0.0024(15) -0.0016(13) C3 0.036(2) 0.039(2) 0.043(2) 0.004(2) -0.002(2) -0.0018(14) C4 0.042(2) 0.051(2) 0.058(3) 0.005(2) 0.008(2) -0.008(2) C5 0.055(2) 0.046(2) 0.055(3) 0.004(2) 0.014(2) -0.011(2) C6 0.062(2) 0.040(2) 0.048(3) 0.009(2) 0.002(2) -0.009(2) C7 0.046(2) 0.036(2) 0.036(2) 0.000(2) -0.005(2) -0.0047(15) C8 0.085(2) 0.047(2) 0.039(2) 0.001(2) -0.016(2) 0.016(2) C9 0.081(2) 0.066(2) 0.075(4) 0.010(2) -0.027(2) 0.020(2) C10 0.051(2) 0.050(2) 0.080(3) 0.000(2) -0.020(2) 0.014(2) C11 0.041(2) 0.042(2) 0.055(3) 0.002(2) -0.008(2) 0.0047(14) C12 0.031(2) 0.046(2) 0.048(3) 0.001(2) -0.007(2) -0.0003(14) C13 0.041(2) 0.048(2) 0.059(3) 0.003(2) -0.013(2) -0.0071(14) C14 0.037(2) 0.045(2) 0.055(3) 0.001(2) -0.012(2) -0.0070(14) C15 0.0323(15) 0.036(2) 0.034(2) 0.005(2) 0.007(2) -0.0021(14) C16 0.047(2) 0.036(2) 0.041(2) 0.003(2) 0.001(2) 0.0001(14) C17 0.054(2) 0.050(2) 0.042(2) 0.002(2) -0.007(2) 0.006(2) C18 0.057(2) 0.046(2) 0.053(3) 0.017(2) 0.006(2) 0.011(2) C19 0.049(2) 0.039(2) 0.060(3) 0.006(2) 0.005(2) -0.0005(15) C20 0.040(2) 0.041(2) 0.040(2) 0.002(2) 0.003(2) -0.0025(14) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag N1 C15 1.381(4) . ? N1 C14 1.467(4) . ? N1 C1 1.468(3) . ? N2 C7 1.390(3) . ? N2 C11 1.445(4) . ? N2 C8 1.450(4) . ? C1 C2 1.533(4) . ? C1 C12 1.544(4) . ? C2 C3 1.391(4) . ? C2 C7 1.397(4) . ? C3 C4 1.385(4) . ? C4 C5 1.361(5) . ? C5 C6 1.386(4) . ? C6 C7 1.407(4) . ? C8 C9 1.527(4) . ? C9 C10 1.526(5) . ? C10 C11 1.522(4) . ? C11 C12 1.518(4) . ? C12 C13 1.529(4) . ? C13 C14 1.516(4) . ? C15 C20 1.397(4) . ? C15 C16 1.404(4) . ? C16 C17 1.379(4) . ? C17 C18 1.372(4) . ? C18 C19 1.379(5) . ? C19 C20 1.381(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 C15 N1 C14 120.7(2) . . ? C15 N1 C1 125.8(2) . . ? C14 N1 C1 111.8(2) . . ? C7 N2 C11 119.6(3) . . ? C7 N2 C8 122.8(3) . . ? C11 N2 C8 111.9(2) . . ? N1 C1 C2 111.7(2) . . ? N1 C1 C12 102.4(2) . . ? C2 C1 C12 111.7(3) . . ? C3 C2 C7 118.0(3) . . ? C3 C2 C1 119.5(3) . . ? C7 C2 C1 122.4(2) . . ? C4 C3 C2 122.4(3) . . ? C5 C4 C3 119.0(3) . . ? C4 C5 C6 120.9(3) . . ? C5 C6 C7 120.1(3) . . ? N2 C7 C2 119.8(3) . . ? N2 C7 C6 120.6(3) . . ? C2 C7 C6 119.5(3) . . ? N2 C8 C9 103.8(3) . . ? C10 C9 C8 106.7(3) . . ? C11 C10 C9 104.4(3) . . ? N2 C11 C12 110.7(3) . . ? N2 C11 C10 102.4(3) . . ? C12 C11 C10 117.3(3) . . ? C11 C12 C13 115.0(3) . . ? C11 C12 C1 111.6(2) . . ? C13 C12 C1 103.0(2) . . ? C14 C13 C12 104.3(3) . . ? N1 C14 C13 105.0(2) . . ? N1 C15 C20 119.9(3) . . ? N1 C15 C16 122.8(2) . . ? C20 C15 C16 117.3(3) . . ? C17 C16 C15 120.5(3) . . ? C18 C17 C16 122.0(3) . . ? C17 C18 C19 117.9(3) . . ? C18 C19 C20 121.5(3) . . ? C19 C20 C15 120.8(3) . . ? _refine_diff_density_max 0.158 _refine_diff_density_min -0.178 _refine_diff_density_rms 0.040 data_if9901 _database_code_CSD 199969 _audit_creation_method SHELXL _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_formula_moiety ? _chemical_formula_structural ? _chemical_formula_analytical ? _chemical_formula_sum 'C20 H22 N2' _chemical_formula_weight 290.40 _chemical_melting_point ? _chemical_compound_source ? 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' _symmetry_cell_setting Triclinic _symmetry_space_group_name_H-M P-1 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 7.4270(10) _cell_length_b 7.8710(10) _cell_length_c 14.5100(10) _cell_angle_alpha 77.140(10) _cell_angle_beta 79.910(10) _cell_angle_gamma 69.900(10) _cell_volume 772.1(2) _cell_formula_units_Z 2 _cell_measurement_temperature 180(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description ? _exptl_crystal_colour colourless _exptl_crystal_size_max 0.28 _exptl_crystal_size_mid 0.23 _exptl_crystal_size_min 0.16 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.249 _exptl_crystal_density_method ? _exptl_crystal_F_000 312 _exptl_absorpt_coefficient_mu 0.073 _exptl_absorpt_correction_type ? _exptl_absorpt_correction_T_min ? _exptl_absorpt_correction_T_max ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 180(2) _diffrn_radiation_wavelength 0.71069 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device NoniusKappa _diffrn_measurement_method ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 4909 _diffrn_reflns_av_R_equivalents 0.0218 _diffrn_reflns_av_sigmaI/netI 0.0464 _diffrn_reflns_limit_h_min -9 _diffrn_reflns_limit_h_max 9 _diffrn_reflns_limit_k_min -9 _diffrn_reflns_limit_k_max 10 _diffrn_reflns_limit_l_min -13 _diffrn_reflns_limit_l_max 18 _diffrn_reflns_theta_min 1.45 _diffrn_reflns_theta_max 27.52 _reflns_number_total 3539 _reflns_number_observed 2689 _reflns_observed_criterion >2sigma(I) _computing_data_collection ? _computing_cell_refinement ? _computing_data_reduction ? _computing_structure_solution teXsan _computing_structure_refinement 'SHELXL-93 (Sheldrick, 1993)' _computing_molecular_graphics ? _computing_publication_material ? _refine_special_details ; Refinement on F^2^ for ALL reflections except for 8 with very negative F^2^ or flagged by the user for potential systematic errors. Weighted R-factors wR and all goodnesses 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 observed criterion of F^2^ > 2sigma(F^2^) is used only for calculating _R_factor_obs 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 w=1/[\s^2^(Fo^2^)+(0.0436P)^2^+0.1621P] 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 ? _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 3531 _refine_ls_number_parameters 199 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0726 _refine_ls_R_factor_obs 0.0455 _refine_ls_wR_factor_all 0.1624 _refine_ls_wR_factor_obs 0.1013 _refine_ls_goodness_of_fit_all 1.039 _refine_ls_goodness_of_fit_obs 1.084 _refine_ls_restrained_S_all 1.504 _refine_ls_restrained_S_obs 1.084 _refine_ls_shift/esd_max 0.000 _refine_ls_shift/esd_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_thermal_displace_type _atom_site_occupancy _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_group N1 N 0.76291(14) -0.04646(14) 0.66045(7) 0.0286(3) Uani 1 d . . N2 N 0.45433(15) 0.18008(15) 0.89317(8) 0.0291(3) Uani 1 d . . C1 C 0.6832(2) 0.0040(2) 0.75336(8) 0.0249(3) Uani 1 d . . H1 H 0.7465(2) -0.0993(2) 0.80324(8) 0.030 Uiso 1 calc R . C2 C 0.7094(2) 0.1780(2) 0.76795(9) 0.0243(3) Uani 1 d . . C3 C 0.8449(2) 0.2541(2) 0.71345(9) 0.0282(3) Uani 1 d . . H3 H 0.9181(2) 0.2034(2) 0.65975(9) 0.034 Uiso 1 calc R . C4 C 0.8750(2) 0.4042(2) 0.73663(10) 0.0334(3) Uani 1 d . . H4 H 0.9663(2) 0.4573(2) 0.69834(10) 0.040 Uiso 1 calc R . C5 C 0.7710(2) 0.4749(2) 0.81556(10) 0.0358(3) Uani 1 d . . H5 H 0.7950(2) 0.5739(2) 0.83297(10) 0.043 Uiso 1 calc R . C6 C 0.6313(2) 0.4037(2) 0.87018(10) 0.0336(3) Uani 1 d . . H6 H 0.5600(2) 0.4545(2) 0.92415(10) 0.040 Uiso 1 calc R . C7 C 0.5963(2) 0.2570(2) 0.84544(9) 0.0262(3) Uani 1 d . . C8 C 0.3160(2) 0.2675(2) 0.96688(10) 0.0372(3) Uani 1 d . . H8A H 0.2629(2) 0.4017(2) 0.94517(10) 0.045 Uiso 1 calc R . H8B H 0.3771(2) 0.2449(2) 1.02575(10) 0.045 Uiso 1 calc R . C9 C 0.1575(2) 0.1767(2) 0.98361(11) 0.0434(4) Uani 1 d . . H9A H 0.1638(2) 0.0920(2) 1.04551(11) 0.052 Uiso 1 calc R . H9B H 0.0284(2) 0.2709(2) 0.98320(11) 0.052 Uiso 1 calc R . C10 C 0.1963(2) 0.0710(2) 0.90161(10) 0.0371(3) Uani 1 d . . H10A H 0.2511(2) -0.0629(2) 0.92392(10) 0.045 Uiso 1 calc R . H10B H 0.0760(2) 0.0952(2) 0.87327(10) 0.045 Uiso 1 calc R . C11 C 0.3408(2) 0.1431(2) 0.82974(9) 0.0288(3) Uani 1 d . . H11 H 0.2690(2) 0.2626(2) 0.79182(9) 0.035 Uiso 1 calc R . C12 C 0.4691(2) 0.0179(2) 0.76117(9) 0.0274(3) Uani 1 d . . H12 H 0.4579(2) -0.1080(2) 0.78426(9) 0.033 Uiso 1 calc R . C13 C 0.4270(2) 0.0782(2) 0.65717(9) 0.0319(3) Uani 1 d . . H13A H 0.3151(2) 0.0458(2) 0.64736(9) 0.038 Uiso 1 calc R . H13B H 0.4008(2) 0.2124(2) 0.63685(9) 0.038 Uiso 1 calc R . C14 C 0.6115(2) -0.0284(2) 0.60296(9) 0.0315(3) Uani 1 d . . H14A H 0.6071(2) -0.1505(2) 0.59826(9) 0.038 Uiso 1 calc R . H14B H 0.6322(2) 0.0401(2) 0.53812(9) 0.038 Uiso 1 calc R . C15 C 0.9490(2) -0.1615(2) 0.64339(9) 0.0278(3) Uani 1 d . . C16 C 1.0848(2) -0.2059(2) 0.70848(10) 0.0328(3) Uani 1 d . . H16 H 1.0498(2) -0.1548(2) 0.76499(10) 0.039 Uiso 1 calc R . C17 C 1.2696(2) -0.3242(2) 0.69048(11) 0.0380(3) Uani 1 d . . H17 H 1.3592(2) -0.3549(2) 0.73564(11) 0.046 Uiso 1 calc R . C18 C 1.3260(2) -0.3983(2) 0.60813(12) 0.0422(4) Uani 1 d . . H18 H 1.4531(2) -0.4787(2) 0.59638(12) 0.051 Uiso 1 calc R . C19 C 1.1942(2) -0.3533(2) 0.54326(11) 0.0429(4) Uani 1 d . . H19 H 1.2315(2) -0.4032(2) 0.48637(11) 0.052 Uiso 1 calc R . C20 C 1.0083(2) -0.2363(2) 0.55991(10) 0.0353(3) Uani 1 d . . H20 H 0.9201(2) -0.2064(2) 0.51415(10) 0.042 Uiso 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 0.0272(5) 0.0332(6) 0.0282(6) -0.0118(5) -0.0033(4) -0.0088(4) N2 0.0283(5) 0.0349(6) 0.0268(6) -0.0095(4) 0.0010(4) -0.0127(5) C1 0.0259(6) 0.0259(6) 0.0244(6) -0.0067(5) -0.0023(5) -0.0089(5) C2 0.0242(6) 0.0248(6) 0.0250(6) -0.0037(5) -0.0061(5) -0.0080(5) C3 0.0272(6) 0.0298(6) 0.0272(7) -0.0042(5) -0.0026(5) -0.0095(5) C4 0.0323(7) 0.0280(7) 0.0415(8) -0.0010(6) -0.0053(6) -0.0142(5) C5 0.0397(7) 0.0264(7) 0.0463(9) -0.0091(6) -0.0079(6) -0.0133(6) C6 0.0374(7) 0.0307(7) 0.0353(8) -0.0120(6) -0.0032(6) -0.0108(6) C7 0.0263(6) 0.0263(6) 0.0263(7) -0.0048(5) -0.0040(5) -0.0083(5) C8 0.0366(7) 0.0421(8) 0.0313(8) -0.0116(6) 0.0057(6) -0.0122(6) C9 0.0339(7) 0.0630(10) 0.0336(8) -0.0103(7) 0.0040(6) -0.0182(7) C10 0.0310(7) 0.0442(8) 0.0369(8) -0.0039(6) 0.0011(6) -0.0172(6) C11 0.0262(6) 0.0323(7) 0.0293(7) -0.0052(5) -0.0028(5) -0.0111(5) C12 0.0277(6) 0.0283(6) 0.0298(7) -0.0053(5) -0.0028(5) -0.0134(5) C13 0.0302(6) 0.0371(7) 0.0326(7) -0.0086(6) -0.0066(5) -0.0129(6) C14 0.0331(7) 0.0361(7) 0.0296(7) -0.0086(5) -0.0067(6) -0.0130(6) C15 0.0304(6) 0.0235(6) 0.0306(7) -0.0054(5) 0.0009(5) -0.0115(5) C16 0.0318(7) 0.0300(7) 0.0394(8) -0.0095(6) -0.0038(6) -0.0114(5) C17 0.0308(7) 0.0312(7) 0.0524(9) -0.0050(6) -0.0071(6) -0.0105(6) C18 0.0324(7) 0.0321(7) 0.0538(10) -0.0071(7) 0.0073(7) -0.0057(6) C19 0.0448(8) 0.0401(8) 0.0357(8) -0.0091(6) 0.0078(7) -0.0076(7) C20 0.0382(7) 0.0349(7) 0.0296(7) -0.0058(6) 0.0018(6) -0.0101(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 N1 C15 1.383(2) . ? N1 C1 1.457(2) . ? N1 C14 1.465(2) . ? N2 C7 1.398(2) . ? N2 C8 1.459(2) . ? N2 C11 1.484(2) . ? C1 C2 1.512(2) . ? C1 C12 1.542(2) . ? C2 C3 1.386(2) . ? C2 C7 1.406(2) . ? C3 C4 1.394(2) . ? C4 C5 1.377(2) . ? C5 C6 1.390(2) . ? C6 C7 1.397(2) . ? C8 C9 1.535(2) . ? C9 C10 1.532(2) . ? C10 C11 1.524(2) . ? C11 C12 1.526(2) . ? C12 C13 1.531(2) . ? C13 C14 1.525(2) . ? C15 C20 1.400(2) . ? C15 C16 1.405(2) . ? C16 C17 1.387(2) . ? C17 C18 1.382(2) . ? C18 C19 1.380(2) . ? C19 C20 1.386(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 C15 N1 C1 122.42(10) . . ? C15 N1 C14 121.29(11) . . ? C1 N1 C14 111.87(10) . . ? C7 N2 C8 119.73(11) . . ? C7 N2 C11 114.36(10) . . ? C8 N2 C11 106.56(10) . . ? N1 C1 C2 114.57(10) . . ? N1 C1 C12 104.27(9) . . ? C2 C1 C12 112.50(10) . . ? C3 C2 C7 119.69(11) . . ? C3 C2 C1 123.61(11) . . ? C7 C2 C1 116.57(11) . . ? C2 C3 C4 120.68(12) . . ? C5 C4 C3 119.35(12) . . ? C4 C5 C6 121.06(12) . . ? C5 C6 C7 119.79(13) . . ? C6 C7 N2 124.36(12) . . ? C6 C7 C2 119.28(12) . . ? N2 C7 C2 116.36(11) . . ? N2 C8 C9 104.34(11) . . ? C10 C9 C8 105.64(11) . . ? C11 C10 C9 104.73(11) . . ? N2 C11 C10 101.48(10) . . ? N2 C11 C12 112.01(10) . . ? C10 C11 C12 117.28(11) . . ? C11 C12 C13 116.04(10) . . ? C11 C12 C1 112.90(10) . . ? C13 C12 C1 102.14(10) . . ? C14 C13 C12 103.71(10) . . ? N1 C14 C13 103.64(10) . . ? N1 C15 C20 120.72(12) . . ? N1 C15 C16 121.33(12) . . ? C20 C15 C16 117.94(12) . . ? C17 C16 C15 120.23(13) . . ? C18 C17 C16 121.27(13) . . ? C19 C18 C17 118.82(13) . . ? C18 C19 C20 120.97(14) . . ? C19 C20 C15 120.75(13) . . ? _refine_diff_density_max 0.211 _refine_diff_density_min -0.180 _refine_diff_density_rms 0.036