# Electronic Supplementary Material (ESI) for Chemical Communications # 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_www #TrackingRef 'compound_3s.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C14 H17 N O2' _chemical_formula_weight 231.29 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 P21/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 8.6775(18) _cell_length_b 18.791(4) _cell_length_c 7.5798(16) _cell_angle_alpha 90.00 _cell_angle_beta 93.790(3) _cell_angle_gamma 90.00 _cell_volume 1233.2(4) _cell_formula_units_Z 4 _cell_measurement_temperature 273(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description ? _exptl_crystal_colour yellow _exptl_crystal_size_max 0.34 _exptl_crystal_size_mid 0.30 _exptl_crystal_size_min 0.22 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.246 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 496 _exptl_absorpt_coefficient_mu 0.083 _exptl_absorpt_correction_type empirical _exptl_absorpt_correction_T_min 0.972 _exptl_absorpt_correction_T_max 0.982 _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 273(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 7783 _diffrn_reflns_av_R_equivalents 0.0321 _diffrn_reflns_av_sigmaI/netI 0.0363 _diffrn_reflns_limit_h_min -10 _diffrn_reflns_limit_h_max 10 _diffrn_reflns_limit_k_min -12 _diffrn_reflns_limit_k_max 23 _diffrn_reflns_limit_l_min -9 _diffrn_reflns_limit_l_max 9 _diffrn_reflns_theta_min 2.17 _diffrn_reflns_theta_max 26.04 _reflns_number_total 2431 _reflns_number_gt 1759 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'Bruker SMART' _computing_data_reduction 'Bruker SMART' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _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^)+(0.0576P)^2^+0.2602P] 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 constr _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 2431 _refine_ls_number_parameters 157 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0784 _refine_ls_R_factor_gt 0.0543 _refine_ls_wR_factor_ref 0.1312 _refine_ls_wR_factor_gt 0.1197 _refine_ls_goodness_of_fit_ref 1.034 _refine_ls_restrained_S_all 1.034 _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 C1 C 0.8269(3) 0.55752(12) 0.5165(3) 0.0587(6) Uani 1 1 d . . . H1A H 0.8059 0.5260 0.6117 0.088 Uiso 1 1 calc R . . H1B H 0.9288 0.5770 0.5369 0.088 Uiso 1 1 calc R . . H1C H 0.8203 0.5317 0.4071 0.088 Uiso 1 1 calc R . . C2 C 0.7102(2) 0.61711(11) 0.5071(3) 0.0438(5) Uani 1 1 d . . . C3 C 0.5580(2) 0.60533(11) 0.4453(3) 0.0445(5) Uani 1 1 d . . . H3 H 0.5282 0.5598 0.4086 0.053 Uiso 1 1 calc R . . C4 C 0.4496(2) 0.65927(11) 0.4367(2) 0.0423(5) Uani 1 1 d . . . H4 H 0.3488 0.6498 0.3936 0.051 Uiso 1 1 calc R . . C5 C 0.4902(2) 0.72723(10) 0.4921(2) 0.0374(4) Uani 1 1 d . . . C6 C 0.6421(2) 0.74004(11) 0.5543(3) 0.0461(5) Uani 1 1 d . . . H6 H 0.6716 0.7854 0.5924 0.055 Uiso 1 1 calc R . . C7 C 0.7493(2) 0.68551(12) 0.5596(3) 0.0488(5) Uani 1 1 d . . . H7 H 0.8507 0.6952 0.5996 0.059 Uiso 1 1 calc R . . C8 C 0.4245(2) 0.85766(11) 0.4537(3) 0.0449(5) Uani 1 1 d . . . H8A H 0.4839 0.8612 0.3500 0.054 Uiso 1 1 calc R . . H8B H 0.4858 0.8763 0.5548 0.054 Uiso 1 1 calc R . . C9 C 0.2709(2) 0.89878(11) 0.4253(3) 0.0423(5) Uani 1 1 d . . . C10 C 0.2819(3) 0.97363(12) 0.4966(3) 0.0637(7) Uani 1 1 d . . . H10A H 0.3557 1.0000 0.4341 0.096 Uiso 1 1 calc R . . H10B H 0.3143 0.9723 0.6202 0.096 Uiso 1 1 calc R . . H10C H 0.1827 0.9962 0.4811 0.096 Uiso 1 1 calc R . . C11 C 0.1598(2) 0.84952(11) 0.5120(2) 0.0419(5) Uani 1 1 d . . . C12 C 0.0560(3) 0.87033(14) 0.6577(3) 0.0634(7) Uani 1 1 d . . . H12A H 0.0413 0.8358 0.7503 0.076 Uiso 1 1 calc R . . H12B H 0.0573 0.9196 0.6959 0.076 Uiso 1 1 calc R . . C13 C -0.0125(2) 0.85416(13) 0.4769(3) 0.0589(6) Uani 1 1 d . . . H13A H -0.0532 0.8936 0.4058 0.071 Uiso 1 1 calc R . . H13B H -0.0693 0.8099 0.4602 0.071 Uiso 1 1 calc R . . C14 C 0.2313(2) 0.77790(11) 0.5284(2) 0.0399(5) Uani 1 1 d . . . N1 N 0.38037(17) 0.78387(8) 0.4845(2) 0.0388(4) Uani 1 1 d . . . O1 O 0.16711(16) 0.72338(8) 0.5751(2) 0.0534(4) Uani 1 1 d . . . O2 O 0.22810(18) 0.90664(8) 0.24141(18) 0.0547(4) Uani 1 1 d . . . H2 H 0.2152 0.8672 0.1963 0.082 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 C1 0.0566(13) 0.0567(16) 0.0631(14) 0.0025(11) 0.0068(11) 0.0190(11) C2 0.0471(12) 0.0429(13) 0.0418(10) 0.0033(9) 0.0067(9) 0.0078(9) C3 0.0509(12) 0.0369(12) 0.0457(11) -0.0025(9) 0.0027(9) 0.0009(10) C4 0.0379(10) 0.0452(13) 0.0431(11) -0.0019(9) -0.0014(8) 0.0007(9) C5 0.0372(10) 0.0374(12) 0.0376(9) 0.0030(8) 0.0028(7) 0.0037(8) C6 0.0403(11) 0.0390(13) 0.0589(13) -0.0030(10) 0.0032(9) -0.0008(9) C7 0.0348(10) 0.0496(14) 0.0612(13) 0.0030(11) -0.0029(9) 0.0045(9) C8 0.0426(11) 0.0394(13) 0.0531(12) 0.0008(9) 0.0063(9) -0.0010(9) C9 0.0461(11) 0.0364(12) 0.0443(11) -0.0013(9) 0.0028(8) 0.0053(9) C10 0.0623(15) 0.0481(16) 0.0807(16) -0.0146(12) 0.0043(12) 0.0042(11) C11 0.0399(10) 0.0436(13) 0.0421(10) 0.0005(9) 0.0017(8) 0.0059(9) C12 0.0610(14) 0.0682(18) 0.0635(15) 0.0035(12) 0.0226(12) 0.0171(12) C13 0.0396(11) 0.0620(16) 0.0750(15) 0.0122(12) 0.0023(10) 0.0098(10) C14 0.0383(10) 0.0411(13) 0.0403(10) 0.0040(9) 0.0022(8) 0.0014(9) N1 0.0347(8) 0.0338(10) 0.0481(9) 0.0026(7) 0.0034(7) 0.0025(7) O1 0.0426(8) 0.0471(10) 0.0713(10) 0.0150(8) 0.0096(7) 0.0004(7) O2 0.0697(10) 0.0448(10) 0.0491(8) 0.0073(7) -0.0011(7) 0.0040(8) _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 1.508(3) . ? C2 C7 1.381(3) . ? C2 C3 1.390(3) . ? C3 C4 1.381(3) . ? C4 C5 1.383(3) . ? C5 C6 1.391(3) . ? C5 N1 1.427(2) . ? C6 C7 1.383(3) . ? C8 N1 1.461(2) . ? C8 C9 1.543(3) . ? C9 O2 1.426(2) . ? C9 C10 1.508(3) . ? C9 C11 1.517(3) . ? C11 C14 1.484(3) . ? C11 C13 1.504(3) . ? C11 C12 1.522(3) . ? C12 C13 1.488(3) . ? C14 O1 1.229(2) . ? C14 N1 1.361(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 C7 C2 C3 117.08(18) . . ? C7 C2 C1 121.73(19) . . ? C3 C2 C1 121.2(2) . . ? C4 C3 C2 121.9(2) . . ? C3 C4 C5 120.28(18) . . ? C4 C5 C6 118.67(18) . . ? C4 C5 N1 121.34(17) . . ? C6 C5 N1 119.99(18) . . ? C7 C6 C5 120.1(2) . . ? C2 C7 C6 121.98(19) . . ? N1 C8 C9 105.36(15) . . ? O2 C9 C10 105.08(17) . . ? O2 C9 C11 110.75(16) . . ? C10 C9 C11 116.13(17) . . ? O2 C9 C8 110.81(16) . . ? C10 C9 C8 112.57(17) . . ? C11 C9 C8 101.63(16) . . ? C14 C11 C13 118.21(18) . . ? C14 C11 C9 108.39(16) . . ? C13 C11 C9 122.76(17) . . ? C14 C11 C12 115.87(18) . . ? C13 C11 C12 58.92(15) . . ? C9 C11 C12 125.54(19) . . ? C13 C12 C11 59.93(14) . . ? C12 C13 C11 61.14(14) . . ? O1 C14 N1 126.53(18) . . ? O1 C14 C11 125.80(17) . . ? N1 C14 C11 107.66(16) . . ? C14 N1 C5 124.85(16) . . ? C14 N1 C8 112.36(15) . . ? C5 N1 C8 122.19(15) . . ? _diffrn_measured_fraction_theta_max 0.999 _diffrn_reflns_theta_full 26.04 _diffrn_measured_fraction_theta_full 0.999 _refine_diff_density_max 0.180 _refine_diff_density_min -0.168 _refine_diff_density_rms 0.037 _database_code_depnum_ccdc_archive 'CCDC 906890' ####################################################################### # # 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_11111 #TrackingRef '3u.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C13 H17 N O2' _chemical_formula_weight 219.28 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 C2/C loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y, -z+1/2' 'x+1/2, y+1/2, z' '-x+1/2, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y, z-1/2' '-x+1/2, -y+1/2, -z' 'x+1/2, -y+1/2, z-1/2' _cell_length_a 22.590(5) _cell_length_b 6.6126(16) _cell_length_c 19.413(5) _cell_angle_alpha 90.00 _cell_angle_beta 122.398(3) _cell_angle_gamma 90.00 _cell_volume 2448.5(10) _cell_formula_units_Z 8 _cell_measurement_temperature 273(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description block _exptl_crystal_colour white _exptl_crystal_size_max 0.25 _exptl_crystal_size_mid 0.22 _exptl_crystal_size_min 0.19 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.190 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 944 _exptl_absorpt_coefficient_mu 0.080 _exptl_absorpt_correction_type empirical _exptl_absorpt_correction_T_min 0.980 _exptl_absorpt_correction_T_max 0.985 _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 273(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 7449 _diffrn_reflns_av_R_equivalents 0.0323 _diffrn_reflns_av_sigmaI/netI 0.0342 _diffrn_reflns_limit_h_min -16 _diffrn_reflns_limit_h_max 27 _diffrn_reflns_limit_k_min -8 _diffrn_reflns_limit_k_max 8 _diffrn_reflns_limit_l_min -23 _diffrn_reflns_limit_l_max 23 _diffrn_reflns_theta_min 2.14 _diffrn_reflns_theta_max 26.03 _reflns_number_total 2403 _reflns_number_gt 1737 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'Bruker SMART' _computing_data_reduction 'Bruker SAINT' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _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^)+(0.0582P)^2^+0.7252P] 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 constr _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 2403 _refine_ls_number_parameters 149 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0744 _refine_ls_R_factor_gt 0.0508 _refine_ls_wR_factor_ref 0.1264 _refine_ls_wR_factor_gt 0.1129 _refine_ls_goodness_of_fit_ref 1.036 _refine_ls_restrained_S_all 1.036 _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 C1 C -0.09987(11) 0.4391(3) 0.25260(12) 0.0551(5) Uani 1 1 d . . . H1 H -0.0626 0.3573 0.2625 0.066 Uiso 1 1 calc R . . C2 C -0.16752(11) 0.3871(3) 0.19322(12) 0.0654(6) Uani 1 1 d . . . H2A H -0.1754 0.2690 0.1635 0.079 Uiso 1 1 calc R . . C3 C -0.22341(11) 0.5044(4) 0.17688(13) 0.0653(6) Uani 1 1 d . . . H3 H -0.2688 0.4671 0.1367 0.078 Uiso 1 1 calc R . . C4 C -0.21107(11) 0.6781(4) 0.22095(13) 0.0697(6) Uani 1 1 d . . . H4 H -0.2486 0.7601 0.2101 0.084 Uiso 1 1 calc R . . C5 C -0.14385(10) 0.7336(3) 0.28123(12) 0.0579(5) Uani 1 1 d . . . H5 H -0.1365 0.8515 0.3109 0.069 Uiso 1 1 calc R . . C6 C -0.08762(9) 0.6144(3) 0.29755(10) 0.0417(4) Uani 1 1 d . . . C7 C -0.00264(10) 0.8866(2) 0.38736(11) 0.0478(5) Uani 1 1 d . . . H7A H -0.0205 0.9200 0.4216 0.057 Uiso 1 1 calc R . . H7B H -0.0223 0.9797 0.3417 0.057 Uiso 1 1 calc R . . C8 C 0.07757(9) 0.8925(2) 0.43611(10) 0.0442(4) Uani 1 1 d . . . C9 C 0.09663(9) 0.6779(2) 0.47301(10) 0.0424(4) Uani 1 1 d . . . C10 C 0.03693(9) 0.5535(2) 0.40618(10) 0.0426(4) Uani 1 1 d . . . C11 C 0.10376(12) 0.9342(3) 0.37984(13) 0.0659(6) Uani 1 1 d . . . H11A H 0.0860 1.0623 0.3533 0.099 Uiso 1 1 calc R . . H11B H 0.0877 0.8294 0.3395 0.099 Uiso 1 1 calc R . . H11C H 0.1541 0.9374 0.4112 0.099 Uiso 1 1 calc R . . C12 C 0.16820(10) 0.5981(3) 0.49518(13) 0.0583(5) Uani 1 1 d . . . H12A H 0.1757 0.4664 0.5193 0.087 Uiso 1 1 calc R . . H12B H 0.2042 0.6885 0.5333 0.087 Uiso 1 1 calc R . . H12C H 0.1697 0.5893 0.4468 0.087 Uiso 1 1 calc R . . C13 C 0.09032(11) 0.6623(3) 0.54819(11) 0.0574(5) Uani 1 1 d . . . H13A H 0.0959 0.5238 0.5655 0.086 Uiso 1 1 calc R . . H13B H 0.0451 0.7101 0.5341 0.086 Uiso 1 1 calc R . . H13C H 0.1261 0.7431 0.5917 0.086 Uiso 1 1 calc R . . N1 N -0.01876(7) 0.6758(2) 0.35912(8) 0.0418(4) Uani 1 1 d . . . O1 O 0.03759(7) 0.36930(18) 0.39833(8) 0.0601(4) Uani 1 1 d . . . O2 O 0.10402(7) 1.03942(18) 0.49953(8) 0.0570(4) Uani 1 1 d . . . H2 H 0.0915 1.1525 0.4795 0.085 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 C1 0.0504(12) 0.0518(11) 0.0553(11) -0.0079(9) 0.0230(10) 0.0011(9) C2 0.0605(15) 0.0638(13) 0.0577(13) -0.0153(10) 0.0222(11) -0.0072(11) C3 0.0464(13) 0.0827(16) 0.0519(12) -0.0051(11) 0.0164(10) -0.0068(12) C4 0.0459(13) 0.0877(17) 0.0605(13) -0.0030(12) 0.0186(11) 0.0136(11) C5 0.0504(13) 0.0580(12) 0.0528(11) -0.0042(9) 0.0193(10) 0.0093(10) C6 0.0425(10) 0.0426(9) 0.0367(9) 0.0060(7) 0.0192(8) 0.0032(8) C7 0.0536(12) 0.0328(9) 0.0469(10) 0.0012(7) 0.0203(9) 0.0066(8) C8 0.0477(11) 0.0338(9) 0.0468(10) 0.0012(7) 0.0226(9) 0.0020(8) C9 0.0403(10) 0.0359(9) 0.0468(10) 0.0031(8) 0.0206(8) 0.0030(7) C10 0.0458(11) 0.0329(9) 0.0489(10) 0.0055(8) 0.0252(9) 0.0058(8) C11 0.0850(17) 0.0552(13) 0.0751(14) 0.0113(10) 0.0545(13) -0.0011(11) C12 0.0444(12) 0.0494(11) 0.0735(13) 0.0012(10) 0.0266(11) 0.0049(9) C13 0.0614(13) 0.0583(12) 0.0464(11) 0.0097(9) 0.0249(10) -0.0002(10) N1 0.0422(9) 0.0330(7) 0.0432(8) 0.0020(6) 0.0181(7) 0.0054(6) O1 0.0573(9) 0.0317(7) 0.0720(9) 0.0011(6) 0.0219(7) 0.0069(6) O2 0.0594(9) 0.0356(7) 0.0571(8) -0.0061(6) 0.0187(7) 0.0006(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 C1 C2 1.377(3) . ? C1 C6 1.386(2) . ? C1 H1 0.9300 . ? C2 C3 1.367(3) . ? C2 H2A 0.9300 . ? C3 C4 1.369(3) . ? C3 H3 0.9300 . ? C4 C5 1.380(3) . ? C4 H4 0.9300 . ? C5 C6 1.380(3) . ? C5 H5 0.9300 . ? C6 N1 1.422(2) . ? C7 N1 1.470(2) . ? C7 C8 1.531(3) . ? C7 H7A 0.9700 . ? C7 H7B 0.9700 . ? C8 O2 1.424(2) . ? C8 C11 1.521(3) . ? C8 C9 1.543(2) . ? C9 C10 1.518(2) . ? C9 C12 1.527(2) . ? C9 C13 1.544(2) . ? C10 O1 1.229(2) . ? C10 N1 1.356(2) . ? C11 H11A 0.9600 . ? C11 H11B 0.9600 . ? C11 H11C 0.9600 . ? C12 H12A 0.9600 . ? C12 H12B 0.9600 . ? C12 H12C 0.9600 . ? C13 H13A 0.9600 . ? C13 H13B 0.9600 . ? C13 H13C 0.9600 . ? O2 H2 0.8200 . ? 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 C2 C1 C6 119.58(19) . . ? C2 C1 H1 120.2 . . ? C6 C1 H1 120.2 . . ? C3 C2 C1 121.7(2) . . ? C3 C2 H2A 119.2 . . ? C1 C2 H2A 119.2 . . ? C2 C3 C4 118.6(2) . . ? C2 C3 H3 120.7 . . ? C4 C3 H3 120.7 . . ? C3 C4 C5 121.1(2) . . ? C3 C4 H4 119.5 . . ? C5 C4 H4 119.5 . . ? C6 C5 C4 120.13(19) . . ? C6 C5 H5 119.9 . . ? C4 C5 H5 119.9 . . ? C5 C6 C1 118.97(17) . . ? C5 C6 N1 119.19(16) . . ? C1 C6 N1 121.84(16) . . ? N1 C7 C8 103.24(13) . . ? N1 C7 H7A 111.1 . . ? C8 C7 H7A 111.1 . . ? N1 C7 H7B 111.1 . . ? C8 C7 H7B 111.1 . . ? H7A C7 H7B 109.1 . . ? O2 C8 C11 110.65(15) . . ? O2 C8 C7 111.17(14) . . ? C11 C8 C7 110.35(16) . . ? O2 C8 C9 110.03(14) . . ? C11 C8 C9 112.40(15) . . ? C7 C8 C9 101.97(13) . . ? C10 C9 C12 112.05(15) . . ? C10 C9 C8 101.67(13) . . ? C12 C9 C8 116.01(15) . . ? C10 C9 C13 106.37(14) . . ? C12 C9 C13 109.30(15) . . ? C8 C9 C13 110.87(14) . . ? O1 C10 N1 125.18(17) . . ? O1 C10 C9 125.38(16) . . ? N1 C10 C9 109.34(14) . . ? C8 C11 H11A 109.5 . . ? C8 C11 H11B 109.5 . . ? H11A C11 H11B 109.5 . . ? C8 C11 H11C 109.5 . . ? H11A C11 H11C 109.5 . . ? H11B C11 H11C 109.5 . . ? C9 C12 H12A 109.5 . . ? C9 C12 H12B 109.5 . . ? H12A C12 H12B 109.5 . . ? C9 C12 H12C 109.5 . . ? H12A C12 H12C 109.5 . . ? H12B C12 H12C 109.5 . . ? C9 C13 H13A 109.5 . . ? C9 C13 H13B 109.5 . . ? H13A C13 H13B 109.5 . . ? C9 C13 H13C 109.5 . . ? H13A C13 H13C 109.5 . . ? H13B C13 H13C 109.5 . . ? C10 N1 C6 126.72(14) . . ? C10 N1 C7 111.05(14) . . ? C6 N1 C7 121.69(14) . . ? C8 O2 H2 109.5 . . ? _diffrn_measured_fraction_theta_max 0.996 _diffrn_reflns_theta_full 26.03 _diffrn_measured_fraction_theta_full 0.996 _refine_diff_density_max 0.165 _refine_diff_density_min -0.186 _refine_diff_density_rms 0.039 _database_code_depnum_ccdc_archive 'CCDC 908363'