# Supplementary Material (ESI) for Perkin Transactions # This journal is © The Royal Society of Chemistry 2000 # CCDC Number: 207/389 data_st-1097 _audit_creation_method SHELXL _chemical_name_systematic ; ? ; _chemical_name_common benzonitrile _chemical_formula_moiety ? _chemical_formula_structural ? _chemical_formula_analytical ? _chemical_formula_sum 'C14 H11 N O' _chemical_formula_weight 209.24 _chemical_melting_point ? _chemical_compound_source 'recrystallized from hexane/ethyl acetate mixed solvents' 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)/n loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, y+1/2, -z+1/2' '-x, -y, -z' 'x-1/2, -y-1/2, z-1/2' _cell_length_a 10.496(1) _cell_length_b 11.407(1) _cell_length_c 18.715(1) _cell_angle_alpha 90.00 _cell_angle_beta 91.53(1) _cell_angle_gamma 90.00 _cell_volume 2239.9(3) _cell_formula_units_Z 8 _cell_measurement_temperature 228(2) _cell_measurement_reflns_used 26 _cell_measurement_theta_min 10 _cell_measurement_theta_max 15 _exptl_crystal_description plates _exptl_crystal_colour pale-yellow _exptl_crystal_size_max 0.40 _exptl_crystal_size_mid 0.30 _exptl_crystal_size_min 0.10 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.241 _exptl_crystal_density_method ? _exptl_crystal_F_000 880 _exptl_absorpt_coefficient_mu 0.079 _exptl_absorpt_correction_type n/a _exptl_absorpt_correction_T_min ? _exptl_absorpt_correction_T_max ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 228(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 'Broker AXS P4 diffractometer' _diffrn_measurement_method '\w/2\q scan' _diffrn_standards_number 3 _diffrn_standards_interval_count 147 _diffrn_standards_interval_time ? _diffrn_standards_decay_% 8.27 _diffrn_reflns_number 4180 _diffrn_reflns_av_R_equivalents 0.0285 _diffrn_reflns_av_sigmaI/netI 0.0480 _diffrn_reflns_limit_h_min 0 _diffrn_reflns_limit_h_max 12 _diffrn_reflns_limit_k_min 0 _diffrn_reflns_limit_k_max 13 _diffrn_reflns_limit_l_min -22 _diffrn_reflns_limit_l_max 22 _diffrn_reflns_theta_min 1.75 _diffrn_reflns_theta_max 25.00 _reflns_number_total 3949 _reflns_number_observed 2506 _reflns_observed_criterion >2sigma(I) _computing_data_collection 'Broker AXS P4 XSCANS' _computing_cell_refinement 'Broker AXS P4 XSCANS' _computing_data_reduction 'Broker AXS P4 XSCANS' _computing_structure_solution 'SHELXS-86 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-93 (Sheldrick, 1993)' _computing_molecular_graphics 'SHELXL-plus (Sheldrick, 1994)' _computing_publication_material 'SHELXL-93 (Sheldrick, 1993)' _refine_special_details ; Refinement on F^2^ for ALL reflections except for 497 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^)+(0.0587P)^2^+0.2188P] 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 SHELXL _refine_ls_extinction_coef 0.0054(8) _refine_ls_extinction_expression 'Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^' _refine_ls_number_reflns 3452 _refine_ls_number_parameters 290 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0901 _refine_ls_R_factor_obs 0.0468 _refine_ls_wR_factor_all 0.1385 _refine_ls_wR_factor_obs 0.1108 _refine_ls_goodness_of_fit_all 1.014 _refine_ls_goodness_of_fit_obs 1.093 _refine_ls_restrained_S_all 1.067 _refine_ls_restrained_S_obs 1.093 _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 C1 C -0.0061(2) 0.8021(2) 0.66399(10) 0.0425(5) Uani 1 d . . C2 C 0.0599(2) 0.8171(2) 0.60064(10) 0.0362(5) Uani 1 d . . C3 C 0.0975(2) 0.9271(2) 0.57673(10) 0.0407(5) Uani 1 d . . C4 C 0.0696(2) 1.0257(2) 0.61689(12) 0.0481(6) Uani 1 d . . H4 H 0.0937(2) 1.0999(2) 0.60176(12) 0.080 Uiso 1 calc R . C5 C 0.0052(2) 1.0114(2) 0.67977(12) 0.0539(6) Uani 1 d . . H5 H -0.0134(2) 1.0769(2) 0.70718(12) 0.080 Uiso 1 calc R . C6 C -0.0320(2) 0.9016(2) 0.70276(12) 0.0523(6) Uani 1 d . . H6 H -0.0753(2) 0.8948(2) 0.74526(12) 0.080 Uiso 1 calc R . C7 C 0.0937(2) 0.7175(2) 0.55814(11) 0.0415(5) Uani 1 d . . N8 N 0.1234(2) 0.6385(2) 0.52524(11) 0.0613(6) Uani 1 d . . O9 O 0.1612(2) 0.92996(14) 0.51527(8) 0.0588(5) Uani 1 d . . C10 C -0.0482(3) 0.6811(2) 0.68609(12) 0.0606(7) Uani 1 d . . H10A H -0.1324(3) 0.6665(2) 0.66545(12) 0.080 Uiso 1 calc R . H10B H 0.0094(3) 0.6241(2) 0.66600(12) 0.080 Uiso 1 calc R . C11 C -0.0523(2) 0.6615(2) 0.76534(11) 0.0429(5) Uani 1 d . . C12 C -0.1658(2) 0.6582(2) 0.80027(13) 0.0578(6) Uani 1 d . . H12 H -0.2417(2) 0.6679(2) 0.77418(13) 0.080 Uiso 1 calc R . C13 C -0.1696(3) 0.6410(2) 0.87281(15) 0.0727(8) Uani 1 d . . H13 H -0.2476(3) 0.6398(2) 0.89523(15) 0.080 Uiso 1 calc R . C14 C -0.0609(4) 0.6259(2) 0.91170(14) 0.0779(9) Uani 1 d . . H14 H -0.0638(4) 0.6150(2) 0.96088(14) 0.080 Uiso 1 calc R . C15 C 0.0530(3) 0.6266(2) 0.8786(2) 0.0747(8) Uani 1 d . . H15 H 0.1280(3) 0.6152(2) 0.9053(2) 0.080 Uiso 1 calc R . C16 C 0.0584(2) 0.6442(2) 0.80551(14) 0.0587(7) Uani 1 d . . H16 H 0.1367(2) 0.6444(2) 0.78343(14) 0.080 Uiso 1 calc R . C21 C 0.4955(2) 0.3151(2) 0.39294(11) 0.0428(5) Uani 1 d . . C22 C 0.3781(2) 0.3224(2) 0.42735(10) 0.0391(5) Uani 1 d . . C23 C 0.3244(2) 0.4305(2) 0.44432(10) 0.0422(5) Uani 1 d . . C24 C 0.3870(2) 0.5328(2) 0.42703(11) 0.0490(6) Uani 1 d . . H24 H 0.3519(2) 0.6053(2) 0.43791(11) 0.080 Uiso 1 calc R . C25 C 0.5009(2) 0.5260(2) 0.39375(12) 0.0534(6) Uani 1 d . . H25 H 0.5430(2) 0.5949(2) 0.38211(12) 0.080 Uiso 1 calc R . C26 C 0.5557(2) 0.4192(2) 0.37681(12) 0.0539(6) Uani 1 d . . H26 H 0.6337(2) 0.4176(2) 0.35438(12) 0.080 Uiso 1 calc R . C27 C 0.3092(2) 0.2195(2) 0.44688(11) 0.0424(5) Uani 1 d . . N28 N 0.2521(2) 0.1392(2) 0.46376(10) 0.0571(5) Uani 1 d . . O29 O 0.21148(15) 0.42677(14) 0.47747(9) 0.0596(5) Uani 1 d . . C30 C 0.5529(2) 0.1981(2) 0.37426(12) 0.0519(6) Uani 1 d . . H30A H 0.5069(2) 0.1366(2) 0.39839(12) 0.080 Uiso 1 calc R . H30B H 0.6407(2) 0.1960(2) 0.39163(12) 0.080 Uiso 1 calc R . C31 C 0.5489(2) 0.1741(2) 0.29472(12) 0.0434(5) Uani 1 d . . C32 C 0.6584(2) 0.1724(2) 0.25550(13) 0.0594(7) Uani 1 d . . H32 H 0.7368(2) 0.1844(2) 0.27862(13) 0.080 Uiso 1 calc R . C33 C 0.5408(3) 0.1345(2) 0.14764(15) 0.0711(8) Uani 1 d . . H33 H 0.5378(3) 0.1221(2) 0.09851(15) 0.080 Uiso 1 calc R . C34 C 0.6538(3) 0.1534(2) 0.18273(15) 0.0709(8) Uani 1 d . . H34 H 0.7289(3) 0.1535(2) 0.15743(15) 0.080 Uiso 1 calc R . C35 C 0.4305(3) 0.1339(2) 0.1859(2) 0.0718(8) Uani 1 d . . H35 H 0.3526(3) 0.1204(2) 0.1625(2) 0.080 Uiso 1 calc R . C36 C 0.4348(2) 0.1532(2) 0.25883(14) 0.0572(6) Uani 1 d . . H36 H 0.3596(2) 0.1521(2) 0.28403(14) 0.080 Uiso 1 calc R . H9 H 0.1936 1.0111 0.5063 0.080 Uiso 1 d . . H29 H 0.1836 0.5055 0.4951 0.080 Uiso 1 d . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 C1 0.0474(13) 0.0452(13) 0.0348(11) -0.0026(9) 0.0015(10) -0.0056(10) C2 0.0363(11) 0.0370(11) 0.0353(11) -0.0025(9) 0.0014(9) 0.0025(9) C3 0.0445(12) 0.0409(12) 0.0369(11) 0.0027(9) 0.0071(9) 0.0015(10) C4 0.0571(14) 0.0368(12) 0.0505(13) 0.0003(10) 0.0037(11) 0.0014(11) C5 0.067(2) 0.0408(13) 0.0547(14) -0.0112(11) 0.0098(12) 0.0071(12) C6 0.0604(15) 0.0552(15) 0.0421(12) -0.0072(11) 0.0144(11) -0.0028(12) C7 0.0454(13) 0.0401(12) 0.0394(12) -0.0016(10) 0.0059(10) -0.0007(10) N8 0.0746(15) 0.0508(12) 0.0593(13) -0.0100(10) 0.0161(11) 0.0027(11) O9 0.0797(11) 0.0477(9) 0.0505(9) 0.0014(7) 0.0265(8) -0.0084(9) C10 0.087(2) 0.0551(15) 0.0403(13) -0.0024(11) 0.0117(12) -0.0219(14) C11 0.0529(14) 0.0364(12) 0.0396(12) 0.0009(9) 0.0071(10) -0.0066(10) C12 0.0521(14) 0.062(2) 0.059(2) 0.0154(12) 0.0116(12) 0.0054(12) C13 0.090(2) 0.068(2) 0.062(2) 0.0118(14) 0.037(2) 0.004(2) C14 0.137(3) 0.056(2) 0.0408(14) 0.0064(12) 0.005(2) -0.006(2) C15 0.090(2) 0.064(2) 0.068(2) 0.0092(14) -0.027(2) -0.006(2) C16 0.053(2) 0.0546(15) 0.068(2) -0.0020(13) 0.0065(13) -0.0073(12) C21 0.0460(13) 0.0472(13) 0.0350(11) 0.0045(9) -0.0001(10) 0.0021(10) C22 0.0459(12) 0.0364(12) 0.0351(11) 0.0032(9) 0.0002(9) -0.0020(10) C23 0.0456(13) 0.0426(13) 0.0383(11) -0.0019(10) 0.0024(10) -0.0032(10) C24 0.064(2) 0.0399(13) 0.0429(12) -0.0003(9) -0.0018(11) -0.0003(11) C25 0.065(2) 0.0466(14) 0.0481(13) 0.0065(11) 0.0037(12) -0.0139(12) C26 0.0500(14) 0.061(2) 0.0506(13) 0.0066(12) 0.0087(11) -0.0066(13) C27 0.0471(13) 0.0402(13) 0.0400(12) 0.0000(10) 0.0034(10) 0.0013(11) N28 0.0648(13) 0.0490(12) 0.0580(12) 0.0054(10) 0.0079(10) -0.0067(11) O29 0.0607(10) 0.0460(9) 0.0732(11) -0.0110(8) 0.0222(9) 0.0005(8) C30 0.0516(14) 0.0540(14) 0.0503(13) 0.0076(11) 0.0045(11) 0.0135(11) C31 0.0437(13) 0.0349(12) 0.0518(13) 0.0027(9) 0.0040(10) 0.0050(10) C32 0.0458(14) 0.074(2) 0.059(2) -0.0042(13) 0.0087(11) -0.0019(13) C33 0.097(2) 0.059(2) 0.057(2) -0.0135(13) -0.004(2) 0.014(2) C34 0.073(2) 0.077(2) 0.064(2) -0.0078(14) 0.0224(15) 0.000(2) C35 0.068(2) 0.061(2) 0.085(2) -0.0206(15) -0.026(2) 0.0136(14) C36 0.0455(14) 0.0516(15) 0.075(2) -0.0111(12) 0.0016(12) 0.0026(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 C1 C2 1.400(3) . y C1 C6 1.378(3) . y C1 C10 1.510(3) . y C2 C3 1.392(3) . y C2 C7 1.437(3) . y C3 O9 1.346(2) . y C3 C4 1.389(3) . y C4 C5 1.382(3) . y C5 C6 1.384(3) . y C7 N8 1.139(3) . y C10 C11 1.502(3) . y C11 C12 1.374(3) . y C11 C16 1.381(3) . y C12 C13 1.373(3) . y C13 C14 1.348(4) . y C14 C15 1.362(4) . y C15 C16 1.385(4) . y C21 C26 1.382(3) . y C21 C22 1.408(3) . y C21 C30 1.508(3) . y C22 C23 1.395(3) . y C22 C27 1.431(3) . y C23 O29 1.353(2) . y C23 C24 1.382(3) . y C24 C25 1.365(3) . y C25 C26 1.388(3) . y C27 N28 1.144(3) . y C30 C31 1.513(3) . y C31 C36 1.379(3) . y C31 C32 1.380(3) . y C32 C34 1.379(3) . y C33 C34 1.358(4) . y C33 C35 1.377(4) . y C35 C36 1.382(4) . y loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C6 C1 C2 117.0(2) . . y C6 C1 C10 123.1(2) . . y C2 C1 C10 119.9(2) . . y C3 C2 C1 122.2(2) . . y C3 C2 C7 117.3(2) . . y C1 C2 C7 120.5(2) . . y O9 C3 C4 124.0(2) . . y O9 C3 C2 116.6(2) . . y C4 C3 C2 119.4(2) . . y C5 C4 C3 118.7(2) . . y C4 C5 C6 121.3(2) . . y C1 C6 C5 121.4(2) . . y N8 C7 C2 178.3(2) . . y C11 C10 C1 115.1(2) . . y C12 C11 C16 117.7(2) . . y C12 C11 C10 121.5(2) . . y C16 C11 C10 120.8(2) . . y C13 C12 C11 121.5(3) . . y C14 C13 C12 120.4(3) . . y C13 C14 C15 119.7(3) . . y C14 C15 C16 120.6(3) . . y C11 C16 C15 120.2(2) . . y C26 C21 C22 117.3(2) . . y C26 C21 C30 121.5(2) . . y C22 C21 C30 121.2(2) . . y C23 C22 C21 121.4(2) . . y C23 C22 C27 117.1(2) . . y C21 C22 C27 121.5(2) . . y O29 C23 C24 124.2(2) . . y O29 C23 C22 116.2(2) . . y C24 C23 C22 119.7(2) . . y C25 C24 C23 119.1(2) . . y C24 C25 C26 121.8(2) . . y C21 C26 C25 120.7(2) . . y N28 C27 C22 178.1(2) . . y C21 C30 C31 112.8(2) . . y C36 C31 C32 117.6(2) . . y C36 C31 C30 120.7(2) . . y C32 C31 C30 121.6(2) . . y C34 C32 C31 121.3(2) . . y C34 C33 C35 119.0(3) . . y C33 C34 C32 120.7(3) . . y C33 C35 C36 120.5(3) . . y C31 C36 C35 120.9(2) . . y _refine_diff_density_max 0.159 _refine_diff_density_min -0.148 _refine_diff_density_rms 0.033