# Electronic Supplementary Material (ESI) for RSC Advances # This journal is © The Royal Society of Chemistry 2012 ####################################################################### # # 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_sa531 _database_code_depnum_ccdc_archive 'CCDC 873921' #TrackingRef 'SA531.CIF' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C14 H15 N O2' _chemical_formula_weight 229.27 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 P1bar loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 7.082(1) _cell_length_b 8.632(1) _cell_length_c 10.345(1) _cell_angle_alpha 65.370(10) _cell_angle_beta 88.98(1) _cell_angle_gamma 83.89(1) _cell_volume 571.36(12) _cell_formula_units_Z 2 _cell_measurement_temperature 198(2) _cell_measurement_reflns_used 30 _cell_measurement_theta_min 5.15 _cell_measurement_theta_max 19.29 _exptl_crystal_description plate _exptl_crystal_colour colorless _exptl_crystal_size_max 0.25 _exptl_crystal_size_mid 0.24 _exptl_crystal_size_min 0.04 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.333 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 244 _exptl_absorpt_coefficient_mu 0.089 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.9780 _exptl_absorpt_correction_T_max 0.9964 _exptl_absorpt_process_details 'SADABS 2.03.(Sheldrick,Bruker AXS Inc.,2002)' _exptl_special_details ; ? ; _diffrn_ambient_temperature 198(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 KappaCCD _diffrn_measurement_method CCD _diffrn_detector_area_resol_mean 9 _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 9798 _diffrn_reflns_av_R_equivalents 0.0443 _diffrn_reflns_av_sigmaI/netI 0.0328 _diffrn_reflns_limit_h_min -8 _diffrn_reflns_limit_h_max 8 _diffrn_reflns_limit_k_min -10 _diffrn_reflns_limit_k_max 10 _diffrn_reflns_limit_l_min -12 _diffrn_reflns_limit_l_max 12 _diffrn_reflns_theta_min 3.56 _diffrn_reflns_theta_max 25.40 _reflns_number_total 2103 _reflns_number_gt 1485 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Collect (Nonius BV, 1997-2000)' _computing_cell_refinement 'Dirax/lsq (Duisenberg & Schreurs, 1989-2000)' _computing_data_reduction 'EvalCCD (Duisenberg & Schreurs 1990-2000)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Schakal-99 (E.Keller 1999)' _computing_publication_material 'XCIF 6.12 (Sheldrick, 1997)' _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^)+(0.0468P)^2^+0.1533P] 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 'refined as riding atoms' _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 2103 _refine_ls_number_parameters 156 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0735 _refine_ls_R_factor_gt 0.0428 _refine_ls_wR_factor_ref 0.1060 _refine_ls_wR_factor_gt 0.0925 _refine_ls_goodness_of_fit_ref 1.061 _refine_ls_restrained_S_all 1.061 _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 N1 N 0.2220(2) 0.61324(19) 0.83957(15) 0.0294(4) Uani 1 1 d . . . C2 C 0.2034(3) 0.7042(3) 0.9211(2) 0.0357(5) Uani 1 1 d . . . H2 H 0.2123 0.6575 1.0220 0.043 Uiso 1 1 calc R . . C3 C 0.1698(3) 0.8739(3) 0.8317(2) 0.0379(5) Uani 1 1 d . . . H3 H 0.1498 0.9663 0.8593 0.045 Uiso 1 1 calc R . . C4 C 0.1700(3) 0.8878(2) 0.6905(2) 0.0324(4) Uani 1 1 d . . . H4 H 0.1503 0.9909 0.6063 0.039 Uiso 1 1 calc R . . C5 C 0.2039(2) 0.7242(2) 0.69783(18) 0.0256(4) Uani 1 1 d . . . C6 C 0.2260(2) 0.6547(2) 0.59104(18) 0.0246(4) Uani 1 1 d . . . C7 C 0.2519(2) 0.7608(2) 0.44771(18) 0.0251(4) Uani 1 1 d . . . H7 H 0.2526 0.8806 0.4186 0.030 Uiso 1 1 calc R . . C8 C 0.2763(2) 0.6928(2) 0.34870(18) 0.0250(4) Uani 1 1 d . . . C9 C 0.2750(2) 0.5157(2) 0.39117(18) 0.0248(4) Uani 1 1 d . . . C10 C 0.2477(2) 0.4117(2) 0.53247(18) 0.0257(4) Uani 1 1 d . . . H10 H 0.2449 0.2921 0.5612 0.031 Uiso 1 1 calc R . . C11 C 0.2241(2) 0.4791(2) 0.63321(18) 0.0248(4) Uani 1 1 d . . . C12 C 0.1908(3) 0.3671(2) 0.78744(19) 0.0314(4) Uani 1 1 d . . . H12A H 0.2467 0.2482 0.8101 0.038 Uiso 1 1 calc R . . H12B H 0.0525 0.3655 0.8023 0.038 Uiso 1 1 calc R . . C13 C 0.2773(3) 0.4295(2) 0.88774(19) 0.0327(5) Uani 1 1 d . . . H13A H 0.2324 0.3672 0.9852 0.039 Uiso 1 1 calc R . . H13B H 0.4174 0.4067 0.8899 0.039 Uiso 1 1 calc R . . O14 O 0.3056(2) 0.78522(15) 0.20657(13) 0.0337(3) Uani 1 1 d . . . C15 C 0.3308(3) 0.9610(2) 0.1626(2) 0.0361(5) Uani 1 1 d . . . H15A H 0.2167 1.0207 0.1830 0.054 Uiso 1 1 calc R . . H15B H 0.3527 1.0129 0.0602 0.054 Uiso 1 1 calc R . . H15C H 0.4405 0.9704 0.2143 0.054 Uiso 1 1 calc R . . O16 O 0.30300(19) 0.46103(15) 0.28496(13) 0.0318(3) Uani 1 1 d . . . C17 C 0.3100(3) 0.2813(2) 0.3235(2) 0.0342(5) Uani 1 1 d . . . H17A H 0.4027 0.2193 0.4021 0.051 Uiso 1 1 calc R . . H17B H 0.3478 0.2574 0.2415 0.051 Uiso 1 1 calc R . . H17C H 0.1843 0.2439 0.3533 0.051 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 N1 0.0302(9) 0.0363(9) 0.0238(8) -0.0147(7) 0.0028(6) -0.0040(7) C2 0.0366(11) 0.0521(13) 0.0293(10) -0.0263(9) 0.0068(8) -0.0122(9) C3 0.0399(12) 0.0463(13) 0.0418(12) -0.0314(10) 0.0077(9) -0.0108(9) C4 0.0335(11) 0.0346(11) 0.0339(10) -0.0185(8) 0.0042(8) -0.0057(8) C5 0.0233(9) 0.0301(10) 0.0254(9) -0.0131(8) 0.0016(7) -0.0046(7) C6 0.0207(9) 0.0288(10) 0.0252(9) -0.0126(8) -0.0002(7) -0.0012(7) C7 0.0267(9) 0.0222(9) 0.0258(9) -0.0096(7) -0.0007(7) -0.0014(7) C8 0.0257(9) 0.0262(9) 0.0223(9) -0.0093(7) -0.0003(7) -0.0025(7) C9 0.0228(9) 0.0298(10) 0.0258(9) -0.0160(8) -0.0007(7) -0.0013(7) C10 0.0257(9) 0.0223(9) 0.0294(10) -0.0111(8) -0.0015(7) -0.0024(7) C11 0.0222(9) 0.0278(10) 0.0232(9) -0.0093(7) -0.0005(7) -0.0030(7) C12 0.0352(11) 0.0297(10) 0.0270(10) -0.0097(8) 0.0023(8) -0.0033(8) C13 0.0365(11) 0.0342(11) 0.0226(9) -0.0077(8) 0.0000(8) -0.0014(8) O14 0.0520(9) 0.0279(7) 0.0216(7) -0.0103(5) 0.0041(6) -0.0068(6) C15 0.0475(12) 0.0277(10) 0.0294(10) -0.0077(8) 0.0085(8) -0.0076(8) O16 0.0437(8) 0.0289(7) 0.0282(7) -0.0170(6) 0.0027(6) -0.0060(6) C17 0.0399(11) 0.0311(11) 0.0390(11) -0.0215(9) 0.0016(9) -0.0059(9) _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 C2 1.368(2) . ? N1 C5 1.376(2) . ? N1 C13 1.460(2) . ? C2 C3 1.365(3) . ? C3 C4 1.414(3) . ? C4 C5 1.377(3) . ? C5 C6 1.460(2) . ? C6 C11 1.393(2) . ? C6 C7 1.402(2) . ? C7 C8 1.377(2) . ? C8 O14 1.374(2) . ? C8 C9 1.405(3) . ? C9 O16 1.369(2) . ? C9 C10 1.383(2) . ? C10 C11 1.390(2) . ? C11 C12 1.512(2) . ? C12 C13 1.517(3) . ? O14 C15 1.421(2) . ? O16 C17 1.427(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 C2 N1 C5 109.65(15) . . ? C2 N1 C13 127.32(16) . . ? C5 N1 C13 122.58(15) . . ? C3 C2 N1 107.83(16) . . ? C2 C3 C4 107.87(17) . . ? C5 C4 C3 107.33(17) . . ? N1 C5 C4 107.31(16) . . ? N1 C5 C6 118.95(15) . . ? C4 C5 C6 133.72(17) . . ? C11 C6 C7 119.56(16) . . ? C11 C6 C5 119.18(15) . . ? C7 C6 C5 121.26(16) . . ? C8 C7 C6 120.57(16) . . ? O14 C8 C7 125.01(16) . . ? O14 C8 C9 115.05(15) . . ? C7 C8 C9 119.93(16) . . ? O16 C9 C10 125.43(16) . . ? O16 C9 C8 115.25(15) . . ? C10 C9 C8 119.31(16) . . ? C9 C10 C11 121.12(16) . . ? C10 C11 C6 119.51(15) . . ? C10 C11 C12 121.54(16) . . ? C6 C11 C12 118.93(16) . . ? C11 C12 C13 112.20(16) . . ? N1 C13 C12 109.53(15) . . ? C8 O14 C15 116.71(14) . . ? C9 O16 C17 117.46(14) . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag C5 N1 C2 C3 1.1(2) . . . . ? C13 N1 C2 C3 173.51(18) . . . . ? N1 C2 C3 C4 -0.7(2) . . . . ? C2 C3 C4 C5 0.1(2) . . . . ? C2 N1 C5 C4 -1.0(2) . . . . ? C13 N1 C5 C4 -173.89(16) . . . . ? C2 N1 C5 C6 177.77(15) . . . . ? C13 N1 C5 C6 4.9(3) . . . . ? C3 C4 C5 N1 0.6(2) . . . . ? C3 C4 C5 C6 -177.97(19) . . . . ? N1 C5 C6 C11 13.6(2) . . . . ? C4 C5 C6 C11 -167.98(19) . . . . ? N1 C5 C6 C7 -165.39(16) . . . . ? C4 C5 C6 C7 13.0(3) . . . . ? C11 C6 C7 C8 -0.3(3) . . . . ? C5 C6 C7 C8 178.72(16) . . . . ? C6 C7 C8 O14 -178.91(16) . . . . ? C6 C7 C8 C9 0.1(3) . . . . ? O14 C8 C9 O16 -0.1(2) . . . . ? C7 C8 C9 O16 -179.14(16) . . . . ? O14 C8 C9 C10 179.59(16) . . . . ? C7 C8 C9 C10 0.5(3) . . . . ? O16 C9 C10 C11 178.70(15) . . . . ? C8 C9 C10 C11 -0.9(3) . . . . ? C9 C10 C11 C6 0.7(3) . . . . ? C9 C10 C11 C12 178.95(16) . . . . ? C7 C6 C11 C10 -0.1(2) . . . . ? C5 C6 C11 C10 -179.14(16) . . . . ? C7 C6 C11 C12 -178.39(16) . . . . ? C5 C6 C11 C12 2.6(2) . . . . ? C10 C11 C12 C13 147.24(17) . . . . ? C6 C11 C12 C13 -34.5(2) . . . . ? C2 N1 C13 C12 152.26(18) . . . . ? C5 N1 C13 C12 -36.2(2) . . . . ? C11 C12 C13 N1 48.8(2) . . . . ? C7 C8 O14 C15 6.4(3) . . . . ? C9 C8 O14 C15 -172.60(16) . . . . ? C10 C9 O16 C17 -1.9(3) . . . . ? C8 C9 O16 C17 177.75(15) . . . . ? _diffrn_measured_fraction_theta_max 0.996 _diffrn_reflns_theta_full 25.40 _diffrn_measured_fraction_theta_full 0.996 _refine_diff_density_max 0.160 _refine_diff_density_min -0.233 _refine_diff_density_rms 0.039