# Electronic Supplementary Material (ESI) for Catalysis Science & Technology # This journal is © The Royal Society of Chemistry 2013 ####################################################################### # # Cambridge Crystallographic Data Centre # CCDC # ####################################################################### # # This CIF contains data from an original supplementary publication # deposited with the CCDC, and may include chemical, crystal, # experimental, refinement, atomic coordinates, # anisotropic displacement parameters and molecular geometry data, # as required by the journal to which it was submitted. # # This CIF is provided on the understanding that it is used for bona # fide research purposes only. It may contain copyright material # of the CCDC or of third parties, and may not be copied or further # disseminated in any form, whether machine-readable or not, # except for the purpose of generating routine backup copies # on your local computer system. # # For further information on the CCDC, data deposition and # data retrieval see: # www.ccdc.cam.ac.uk # # Bona fide researchers may freely download Mercury and enCIFer # from this site to visualise CIF-encoded structures and # to carry out CIF format checking respectively. # ####################################################################### data_a _database_code_depnum_ccdc_archive 'CCDC 884042' #TrackingRef 'cif-1.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C14 H16 N2 O2' _chemical_formula_weight 244.30 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 ? _symmetry_space_group_name_H-M 'P 21/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 5.8113(2) _cell_length_b 23.7797(8) _cell_length_c 9.2207(3) _cell_angle_alpha 90.00 _cell_angle_beta 95.959(2) _cell_angle_gamma 90.00 _cell_volume 1267.33(7) _cell_formula_units_Z 4 _cell_measurement_temperature 296(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description ? _exptl_crystal_colour ? _exptl_crystal_size_max 0.43 _exptl_crystal_size_mid 0.42 _exptl_crystal_size_min 0.41 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.286 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 524 _exptl_absorpt_coefficient_mu 0.087 _exptl_absorpt_correction_type empirical _exptl_absorpt_correction_T_min 0.963 _exptl_absorpt_correction_T_max 0.965 _exptl_absorpt_process_details sadabs _exptl_special_details ; ? ; _diffrn_ambient_temperature 296(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 ? _diffrn_measurement_method ? _diffrn_detector_area_resol_mean ? _diffrn_reflns_number 14781 _diffrn_reflns_av_R_equivalents 0.0293 _diffrn_reflns_av_sigmaI/netI 0.0236 _diffrn_reflns_limit_h_min -7 _diffrn_reflns_limit_h_max 7 _diffrn_reflns_limit_k_min -30 _diffrn_reflns_limit_k_max 30 _diffrn_reflns_limit_l_min -11 _diffrn_reflns_limit_l_max 11 _diffrn_reflns_theta_min 1.71 _diffrn_reflns_theta_max 27.09 _reflns_number_total 2779 _reflns_number_gt 2312 _reflns_threshold_expression >2sigma(I) _computing_data_collection ? _computing_cell_refinement ? _computing_data_reduction ? _computing_structure_solution 'SHELXS-97 (Sheldrick, 2008)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 2008)' _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^)+(0.1301P)^2^+0.7855P] 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 2779 _refine_ls_number_parameters 171 _refine_ls_number_restraints 3 _refine_ls_R_factor_all 0.0509 _refine_ls_R_factor_gt 0.0425 _refine_ls_wR_factor_ref 0.1396 _refine_ls_wR_factor_gt 0.1251 _refine_ls_goodness_of_fit_ref 0.646 _refine_ls_restrained_S_all 0.647 _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 0.2539(2) 0.20664(4) 0.68822(13) 0.0562(3) Uani 1 1 d . . . O2 O -0.0216(2) 0.08666(4) 1.03373(12) 0.0524(3) Uani 1 1 d . . . C7 C 0.0471(2) 0.25923(5) 0.89935(13) 0.0351(3) Uani 1 1 d . . . N2 N -0.1359(2) 0.19264(5) 1.03941(14) 0.0440(3) Uani 1 1 d D . . H@1 H -0.184(3) 0.2217(6) 1.081(2) 0.066 Uiso 1 1 d D . . H@3 H -0.156(3) 0.1590(5) 1.069(2) 0.066 Uiso 1 1 d D . . C1 C 0.5539(3) 0.01818(6) 0.73122(19) 0.0502(4) Uani 1 1 d . . . H1A H 0.4982 -0.0195 0.7401 0.075 Uiso 1 1 calc R . . H1B H 0.6803 0.0248 0.8048 0.075 Uiso 1 1 calc R . . H1C H 0.6056 0.0232 0.6365 0.075 Uiso 1 1 calc R . . C2 C 0.3589(2) 0.05974(5) 0.75068(14) 0.0351(3) Uani 1 1 d . . . C3 C 0.2807(3) 0.05382(5) 0.90301(16) 0.0411(3) Uani 1 1 d . . . H3A H 0.2069 0.0175 0.9097 0.049 Uiso 1 1 calc R . . H3B H 0.4168 0.0542 0.9735 0.049 Uiso 1 1 calc R . . C4 C 0.1166(2) 0.09847(5) 0.94506(14) 0.0359(3) Uani 1 1 d . . . C5 C 0.1317(2) 0.15479(5) 0.88441(13) 0.0336(3) Uani 1 1 d . . . C6 C 0.0106(2) 0.19947(5) 0.94054(14) 0.0342(3) Uani 1 1 d . . . C8 C -0.1287(3) 0.28981(6) 0.82387(17) 0.0477(4) Uani 1 1 d . . . H8 H -0.2718 0.2735 0.7957 0.057 Uiso 1 1 calc R . . C9 C -0.0863(4) 0.34535(8) 0.7913(2) 0.0631(5) Uani 1 1 d . . . H9 H -0.2050 0.3657 0.7402 0.076 Uiso 1 1 calc R . . N1 N 0.1132(3) 0.37152(6) 0.82843(19) 0.0677(5) Uani 1 1 d . . . C11 C 0.2536(3) 0.28616(6) 0.94274(17) 0.0444(3) Uani 1 1 d . . . H11 H 0.3737 0.2673 0.9968 0.053 Uiso 1 1 calc R . . C10 C 0.2771(3) 0.34166(7) 0.9039(2) 0.0575(4) Uani 1 1 d . . . H10 H 0.4173 0.3593 0.9325 0.069 Uiso 1 1 calc R . . C13 C 0.4465(2) 0.11986(5) 0.73564(16) 0.0403(3) Uani 1 1 d . . . H12A H 0.5849 0.1250 0.8027 0.048 Uiso 1 1 calc R . . H12B H 0.4893 0.1250 0.6376 0.048 Uiso 1 1 calc R . . C12 C 0.2736(2) 0.16427(5) 0.76520(14) 0.0364(3) Uani 1 1 d . . . C14 C 0.1573(3) 0.04817(7) 0.63520(19) 0.0533(4) Uani 1 1 d . . . H14A H 0.1052 0.0102 0.6446 0.080 Uiso 1 1 calc R . . H14B H 0.2069 0.0535 0.5400 0.080 Uiso 1 1 calc R . . H14C H 0.0328 0.0736 0.6482 0.080 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 0.0893(9) 0.0350(5) 0.0495(6) 0.0107(4) 0.0324(6) 0.0065(5) O2 0.0717(7) 0.0366(5) 0.0547(6) 0.0041(4) 0.0339(6) -0.0024(5) C7 0.0433(7) 0.0304(6) 0.0326(6) -0.0024(5) 0.0086(5) 0.0044(5) N2 0.0534(7) 0.0357(6) 0.0462(7) -0.0056(5) 0.0210(6) 0.0007(5) C1 0.0502(8) 0.0405(7) 0.0618(9) -0.0062(7) 0.0145(7) 0.0087(6) C2 0.0390(7) 0.0292(6) 0.0382(7) -0.0041(5) 0.0086(5) 0.0007(5) C3 0.0528(8) 0.0303(6) 0.0417(7) 0.0049(5) 0.0119(6) 0.0035(5) C4 0.0466(7) 0.0307(6) 0.0315(6) -0.0007(5) 0.0095(5) -0.0031(5) C5 0.0418(7) 0.0284(6) 0.0319(6) 0.0000(4) 0.0096(5) 0.0005(5) C6 0.0385(7) 0.0323(6) 0.0319(6) -0.0026(5) 0.0038(5) -0.0001(5) C8 0.0500(8) 0.0484(8) 0.0445(8) 0.0052(6) 0.0041(6) 0.0092(6) C9 0.0815(13) 0.0515(9) 0.0585(10) 0.0186(8) 0.0177(9) 0.0252(9) N1 0.0968(12) 0.0356(7) 0.0767(10) 0.0081(7) 0.0370(9) 0.0066(7) C11 0.0461(8) 0.0379(7) 0.0493(8) -0.0047(6) 0.0054(6) -0.0012(6) C10 0.0667(10) 0.0403(8) 0.0690(11) -0.0108(7) 0.0236(8) -0.0115(7) C13 0.0438(7) 0.0347(7) 0.0451(7) -0.0015(5) 0.0176(6) -0.0037(5) C12 0.0480(7) 0.0286(6) 0.0341(6) -0.0009(5) 0.0116(5) -0.0035(5) C14 0.0508(9) 0.0558(9) 0.0526(9) -0.0153(7) 0.0013(7) -0.0016(7) _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 C12 1.2308(16) . ? O2 C4 1.2365(16) . ? C7 C8 1.3821(19) . ? C7 C11 1.382(2) . ? C7 C6 1.4917(17) . ? N2 C6 1.3204(18) . ? N2 H@1 0.853(9) . ? N2 H@3 0.857(9) . ? C1 C2 1.5282(18) . ? C1 H1A 0.9600 . ? C1 H1B 0.9600 . ? C1 H1C 0.9600 . ? C2 C14 1.524(2) . ? C2 C3 1.5268(19) . ? C2 C13 1.5289(17) . ? C3 C4 1.5047(18) . ? C3 H3A 0.9700 . ? C3 H3B 0.9700 . ? C4 C5 1.4575(17) . ? C5 C6 1.4028(17) . ? C5 C12 1.4584(17) . ? C8 C9 1.382(2) . ? C8 H8 0.9300 . ? C9 N1 1.329(3) . ? C9 H9 0.9300 . ? N1 C10 1.326(3) . ? C11 C10 1.378(2) . ? C11 H11 0.9300 . ? C10 H10 0.9300 . ? C13 C12 1.5023(18) . ? C13 H12A 0.9700 . ? C13 H12B 0.9700 . ? C14 H14A 0.9600 . ? C14 H14B 0.9600 . ? C14 H14C 0.9600 . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C8 C7 C11 118.44(13) . . ? C8 C7 C6 120.81(13) . . ? C11 C7 C6 120.66(12) . . ? C6 N2 H@1 118.6(14) . . ? C6 N2 H@3 116.8(13) . . ? H@1 N2 H@3 123.4(19) . . ? C2 C1 H1A 109.5 . . ? C2 C1 H1B 109.5 . . ? H1A C1 H1B 109.5 . . ? C2 C1 H1C 109.5 . . ? H1A C1 H1C 109.5 . . ? H1B C1 H1C 109.5 . . ? C14 C2 C3 110.22(12) . . ? C14 C2 C1 109.07(12) . . ? C3 C2 C1 110.09(11) . . ? C14 C2 C13 110.16(12) . . ? C3 C2 C13 107.66(10) . . ? C1 C2 C13 109.63(11) . . ? C4 C3 C2 115.41(11) . . ? C4 C3 H3A 108.4 . . ? C2 C3 H3A 108.4 . . ? C4 C3 H3B 108.4 . . ? C2 C3 H3B 108.4 . . ? H3A C3 H3B 107.5 . . ? O2 C4 C5 122.11(12) . . ? O2 C4 C3 118.87(12) . . ? C5 C4 C3 118.97(11) . . ? C6 C5 C4 120.12(11) . . ? C6 C5 C12 120.37(11) . . ? C4 C5 C12 119.51(11) . . ? N2 C6 C5 123.08(12) . . ? N2 C6 C7 114.33(11) . . ? C5 C6 C7 122.50(11) . . ? C7 C8 C9 118.23(16) . . ? C7 C8 H8 120.9 . . ? C9 C8 H8 120.9 . . ? N1 C9 C8 124.20(16) . . ? N1 C9 H9 117.9 . . ? C8 C9 H9 117.9 . . ? C10 N1 C9 116.39(14) . . ? C10 C11 C7 118.37(15) . . ? C10 C11 H11 120.8 . . ? C7 C11 H11 120.8 . . ? N1 C10 C11 124.33(16) . . ? N1 C10 H10 117.8 . . ? C11 C10 H10 117.8 . . ? C12 C13 C2 113.92(11) . . ? C12 C13 H12A 108.8 . . ? C2 C13 H12A 108.8 . . ? C12 C13 H12B 108.8 . . ? C2 C13 H12B 108.8 . . ? H12A C13 H12B 107.7 . . ? O1 C12 C5 122.36(12) . . ? O1 C12 C13 119.65(12) . . ? C5 C12 C13 117.99(11) . . ? C2 C14 H14A 109.5 . . ? C2 C14 H14B 109.5 . . ? H14A C14 H14B 109.5 . . ? C2 C14 H14C 109.5 . . ? H14A C14 H14C 109.5 . . ? H14B C14 H14C 109.5 . . ? _diffrn_measured_fraction_theta_max 0.994 _diffrn_reflns_theta_full 27.09 _diffrn_measured_fraction_theta_full 0.994 _refine_diff_density_max 0.225 _refine_diff_density_min -0.189 _refine_diff_density_rms 0.039