# Electronic Supplementary Material (ESI) for RSC Advances # 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_jw19_a_manual _audit_creation_date 2013-07-03 _audit_creation_method ; Olex2 1.2 (compiled Apr 23 2013 17:59:47, GUI svn.r4466) ; _chemical_name_common ? _chemical_name_systematic ; ? ; _chemical_formula_moiety 'C17 H20 N2 O3' _chemical_formula_sum 'C17 H20 N2 O3' _chemical_formula_weight 300.35 _chemical_melting_point ? _chemical_oxdiff_formula 'C11 H10 N O' loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0181 0.0091 '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 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _space_group_crystal_system monoclinic _space_group_IT_number 14 _space_group_name_H-M_alt 'P 1 21/n 1' _space_group_name_Hall '-P 2yn' loop_ _space_group_symop_id _space_group_symop_operation_xyz 1 'x, y, z' 2 '-x+1/2, y+1/2, -z+1/2' 3 '-x, -y, -z' 4 'x-1/2, -y-1/2, z-1/2' _cell_length_a 12.5132(9) _cell_length_b 9.0524(4) _cell_length_c 14.4988(10) _cell_angle_alpha 90.00 _cell_angle_beta 111.345(8) _cell_angle_gamma 90.00 _cell_volume 1529.67(17) _cell_formula_units_Z 4 _cell_measurement_reflns_used 2776 _cell_measurement_temperature 101(2) _cell_measurement_theta_max 73.8510 _cell_measurement_theta_min 4.0340 _exptl_absorpt_coefficient_mu 0.732 _exptl_absorpt_correction_T_max 1.00000 _exptl_absorpt_correction_T_min 0.78019 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details ; CrysAlisPro, Agilent Technologies, Version 1.171.36.28e (release 10-06-2013 CrysAlis171 .NET) (compiled Jun 10 2013,11:58:50) Empirical absorption correction using spherical harmonics, implemented in SCALE3 ABSPACK scaling algorithm. ; _exptl_crystal_colour yellow _exptl_crystal_colour_primary yellow _exptl_crystal_density_diffrn 1.304 _exptl_crystal_density_meas ? _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 640 _exptl_crystal_size_max 0.3 _exptl_crystal_size_mid 0.2 _exptl_crystal_size_min 0.15 _exptl_special_details ; ? ; _diffrn_reflns_av_R_equivalents 0.0405 _diffrn_reflns_av_unetI/netI 0.0471 _diffrn_reflns_limit_h_max 14 _diffrn_reflns_limit_h_min -14 _diffrn_reflns_limit_k_max 7 _diffrn_reflns_limit_k_min -10 _diffrn_reflns_limit_l_max 16 _diffrn_reflns_limit_l_min -17 _diffrn_reflns_number 5359 _diffrn_reflns_theta_full 66.50 _diffrn_reflns_theta_max 66.56 _diffrn_reflns_theta_min 4.01 _diffrn_ambient_temperature 101(2) _diffrn_detector_area_resol_mean 5.3095 _diffrn_measured_fraction_theta_full 0.9969 _diffrn_measured_fraction_theta_max 0.9622 _diffrn_measurement_details ; #__ type_ start__ end____ width___ exp.time_ 1 omega -107.00 -21.00 1.0000 1.0000 omega____ theta____ kappa____ phi______ frames - -38.5000 -57.0000 -180.0000 86 #__ type_ start__ end____ width___ exp.time_ 2 omega -54.00 -5.00 1.0000 1.0000 omega____ theta____ kappa____ phi______ frames - -38.5000 125.0000 30.0000 49 #__ type_ start__ end____ width___ exp.time_ 3 omega -90.00 -5.00 1.0000 1.0000 omega____ theta____ kappa____ phi______ frames - -38.5000 125.0000 120.0000 85 #__ type_ start__ end____ width___ exp.time_ 4 omega 38.00 131.00 1.0000 3.0800 omega____ theta____ kappa____ phi______ frames - 104.9775 -61.0000 0.0000 93 #__ type_ start__ end____ width___ exp.time_ 5 omega 100.00 133.00 1.0000 3.0800 omega____ theta____ kappa____ phi______ frames - 104.9775 125.0000 -30.0000 33 #__ type_ start__ end____ width___ exp.time_ 6 omega 150.00 175.00 1.0000 3.0800 omega____ theta____ kappa____ phi______ frames - 104.9775 125.0000 -30.0000 25 #__ type_ start__ end____ width___ exp.time_ 7 omega 35.00 97.00 1.0000 3.0800 omega____ theta____ kappa____ phi______ frames - 104.9775 -45.0000 -120.0000 62 #__ type_ start__ end____ width___ exp.time_ 8 omega 51.00 82.00 1.0000 3.0800 omega____ theta____ kappa____ phi______ frames - 104.9775 -30.0000 -180.0000 31 #__ type_ start__ end____ width___ exp.time_ 9 omega 37.00 89.00 1.0000 3.0800 omega____ theta____ kappa____ phi______ frames - 104.9775 -45.0000 -180.0000 52 #__ type_ start__ end____ width___ exp.time_ 10 omega 79.00 173.00 1.0000 3.0800 omega____ theta____ kappa____ phi______ frames - 104.9775 61.0000 150.0000 94 ; _diffrn_measurement_device_type 'SuperNova, Dual, Cu at zero, Atlas' _diffrn_measurement_method '\w scans' _diffrn_orient_matrix_UB_11 -0.0900150000 _diffrn_orient_matrix_UB_12 0.0241116000 _diffrn_orient_matrix_UB_13 -0.1045860000 _diffrn_orient_matrix_UB_21 0.0912962000 _diffrn_orient_matrix_UB_22 0.0764018000 _diffrn_orient_matrix_UB_23 -0.0317048000 _diffrn_orient_matrix_UB_31 0.0319845000 _diffrn_orient_matrix_UB_32 -0.1500988000 _diffrn_orient_matrix_UB_33 -0.0327742000 _diffrn_radiation_monochromator mirror _diffrn_radiation_type 'Cu K\a' _diffrn_radiation_wavelength 1.5418 _diffrn_source 'SuperNova (Cu) X-ray Source' _diffrn_standards_decay_% ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_number ? _reflns_number_gt 2244 _reflns_number_total 2696 _reflns_odcompleteness_completeness 99.69 _reflns_odcompleteness_iscentric 1 _reflns_odcompleteness_theta 66.97 _reflns_threshold_expression >2sigma(I) _computing_cell_refinement ; CrysAlisPro, Agilent Technologies, Version 1.171.36.28e (release 10-06-2013 CrysAlis171 .NET) (compiled Jun 10 2013,11:58:50) ; _computing_data_collection ; CrysAlisPro, Agilent Technologies, Version 1.171.36.28e (release 10-06-2013 CrysAlis171 .NET) (compiled Jun 10 2013,11:58:50) ; _computing_data_reduction ; CrysAlisPro, Agilent Technologies, Version 1.171.36.28e (release 10-06-2013 CrysAlis171 .NET) (compiled Jun 10 2013,11:58:50) ; _computing_molecular_graphics ; O. V. Dolomanov, L. J. Bourhis, R. J. Gildea, J. A. K. Howard and H. Puschmann, OLEX2: a complete structure solution, refinement and analysis program. J. Appl. Cryst. (2009). 42, 339-341. ; _computing_publication_material ; O. V. Dolomanov, L. J. Bourhis, R. J. Gildea, J. A. K. Howard and H. Puschmann, OLEX2: a complete structure solution, refinement and analysis program. J. Appl. Cryst. (2009). 42, 339-341. ; _computing_structure_refinement ; SHELXL, G.M. Sheldrick, Acta Cryst. (2008). A64, 112-122 ; _computing_structure_solution ; olex2.solve (L.J. Bourhis, O.V. Dolomanov, R.J. Gildea, J.A.K. Howard, H. Puschmann, in preparation, 2011) ; _refine_diff_density_max 0.272 _refine_diff_density_min -0.268 _refine_diff_density_rms 0.049 _refine_ls_extinction_coef ? _refine_ls_extinction_method none _refine_ls_goodness_of_fit_ref 1.048 _refine_ls_hydrogen_treatment mixed _refine_ls_matrix_type full _refine_ls_number_parameters 202 _refine_ls_number_reflns 2696 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0511 _refine_ls_R_factor_gt 0.0422 _refine_ls_restrained_S_all 1.048 _refine_ls_shift/su_max 0.001 _refine_ls_shift/su_mean 0.000 _refine_ls_structure_factor_coef Fsqd _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0532P)^2^+0.1715P] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_gt 0.1025 _refine_ls_wR_factor_ref 0.1111 _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. ; _olex2_refinement_description ; 1. Fixed Uiso At 1.2 times of: All C(H) groups, All C(H,H) groups At 1.5 times of: All C(H,H,H) groups 2.a Ternary CH refined with riding coordinates: C10(H10), C9(H9), C8(H8), C11(H11) 2.b Secondary CH2 refined with riding coordinates: C16(H16A,H16B) 2.c Aromatic/amide H refined with riding coordinates: C4(H4), C5(H5), C3(H3), C1(H1), C2(H2) 2.d Idealised Me refined as rotating group: C17(H17A,H17B,H17C), C15(H15A,H15B,H15C), C14(H14A,H14B,H14C) ; _atom_sites_solution_hydrogens geom _atom_sites_solution_primary iterative _atom_sites_solution_secondary difmap 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 O2 O 0.14521(10) -0.16303(12) 0.61687(9) 0.0276(3) Uani 1 1 d . . . O1 O 0.09532(10) 0.39913(11) 0.66946(8) 0.0224(3) Uani 1 1 d . . . O3 O 0.47814(10) 0.03963(13) 0.61821(10) 0.0293(3) Uani 1 1 d . . . N1 N 0.31451(12) -0.08640(14) 0.60497(10) 0.0210(3) Uani 1 1 d . . . N2 N 0.17921(11) 0.25630(13) 0.53123(10) 0.0183(3) Uani 1 1 d . . . C13 C 0.38566(14) 0.03640(17) 0.62724(12) 0.0207(3) Uani 1 1 d . . . C4 C -0.17973(14) 0.01782(18) 0.64311(12) 0.0246(4) Uani 1 1 d . . . H4 H -0.2047 -0.0785 0.6254 0.029 Uiso 1 1 calc R . . C5 C -0.08040(14) 0.06796(17) 0.63181(11) 0.0206(3) Uani 1 1 d . . . H5 H -0.0383 0.0044 0.6077 0.025 Uiso 1 1 calc R . . C12 C 0.21765(14) -0.06860(16) 0.62680(11) 0.0198(3) Uani 1 1 d . . . C10 C 0.32920(13) 0.15779(16) 0.66613(11) 0.0179(3) Uani 1 1 d . . . H10 H 0.3774 0.1846 0.7341 0.021 Uiso 1 1 calc R . . C17 C 0.49081(15) 0.39346(19) 0.61745(14) 0.0287(4) Uani 1 1 d . . . H17A H 0.5371 0.4228 0.5804 0.043 Uiso 1 1 calc R . . H17B H 0.5274 0.3132 0.6607 0.043 Uiso 1 1 calc R . . H17C H 0.4819 0.4755 0.6560 0.043 Uiso 1 1 calc R . . C15 C 0.11334(14) 0.37210(18) 0.46447(13) 0.0239(4) Uani 1 1 d . . . H15A H 0.0350 0.3409 0.4334 0.036 Uiso 1 1 calc R . . H15B H 0.1454 0.3905 0.4147 0.036 Uiso 1 1 calc R . . H15C H 0.1163 0.4609 0.5015 0.036 Uiso 1 1 calc R . . C9 C 0.21591(13) 0.08814(16) 0.66321(11) 0.0183(3) Uani 1 1 d . . . H9 H 0.2093 0.0899 0.7285 0.022 Uiso 1 1 calc R . . C3 C -0.24195(15) 0.11102(19) 0.68083(13) 0.0265(4) Uani 1 1 d . . . H3 H -0.3088 0.0777 0.6879 0.032 Uiso 1 1 calc R . . C7 C 0.05970(14) 0.27547(16) 0.64036(11) 0.0180(3) Uani 1 1 d . . . C14 C 0.34472(16) -0.22515(18) 0.56990(14) 0.0287(4) Uani 1 1 d . . . H14A H 0.4015 -0.2072 0.5411 0.043 Uiso 1 1 calc R . . H14B H 0.2776 -0.2674 0.5209 0.043 Uiso 1 1 calc R . . H14C H 0.3749 -0.2924 0.6245 0.043 Uiso 1 1 calc R . . C8 C 0.11933(13) 0.17954(16) 0.58626(11) 0.0177(3) Uani 1 1 d . . . H8 H 0.0630 0.1118 0.5416 0.021 Uiso 1 1 calc R . . C1 C -0.10546(14) 0.30539(18) 0.69572(12) 0.0215(3) Uani 1 1 d . . . H1 H -0.0806 0.4016 0.7139 0.026 Uiso 1 1 calc R . . C6 C -0.04318(14) 0.21327(17) 0.65629(11) 0.0188(3) Uani 1 1 d . . . C16 C 0.37340(14) 0.34409(17) 0.54642(12) 0.0229(4) Uani 1 1 d . . . H16A H 0.3830 0.2619 0.5072 0.027 Uiso 1 1 calc R . . H16B H 0.3379 0.4245 0.5015 0.027 Uiso 1 1 calc R . . C11 C 0.29405(14) 0.29724(16) 0.59986(11) 0.0186(3) Uani 1 1 d . . . H11 H 0.2865 0.3800 0.6406 0.022 Uiso 1 1 calc R . . C2 C -0.20371(15) 0.25462(19) 0.70796(13) 0.0257(4) Uani 1 1 d . . . H2 H -0.2444 0.3167 0.7344 0.031 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 O2 0.0270(7) 0.0185(6) 0.0365(7) 0.0017(5) 0.0104(5) -0.0024(5) O1 0.0236(6) 0.0184(6) 0.0250(6) -0.0042(4) 0.0085(5) -0.0016(4) O3 0.0230(7) 0.0271(6) 0.0405(7) 0.0033(5) 0.0147(5) 0.0056(5) N1 0.0239(7) 0.0180(6) 0.0196(7) -0.0003(5) 0.0063(6) 0.0037(5) N2 0.0177(7) 0.0182(6) 0.0178(7) 0.0023(5) 0.0051(5) 0.0005(5) C13 0.0203(8) 0.0205(7) 0.0192(8) 0.0038(6) 0.0047(6) 0.0039(6) C4 0.0280(9) 0.0222(8) 0.0241(8) 0.0006(6) 0.0101(7) -0.0033(6) C5 0.0242(9) 0.0213(7) 0.0176(8) -0.0005(6) 0.0092(7) 0.0005(6) C12 0.0224(8) 0.0184(7) 0.0164(7) 0.0028(6) 0.0043(6) 0.0021(6) C10 0.0188(8) 0.0172(7) 0.0163(7) 0.0003(6) 0.0050(6) 0.0003(6) C17 0.0232(9) 0.0254(8) 0.0368(10) 0.0028(7) 0.0102(8) -0.0022(7) C15 0.0205(8) 0.0250(8) 0.0242(8) 0.0070(6) 0.0057(7) 0.0018(6) C9 0.0195(8) 0.0191(7) 0.0166(7) 0.0010(6) 0.0068(6) 0.0019(6) C3 0.0218(9) 0.0331(9) 0.0272(9) 0.0023(7) 0.0119(7) -0.0023(7) C7 0.0180(8) 0.0184(7) 0.0157(7) 0.0025(6) 0.0039(6) 0.0027(6) C14 0.0322(10) 0.0213(8) 0.0290(9) -0.0033(7) 0.0069(8) 0.0081(7) C8 0.0180(8) 0.0170(7) 0.0180(7) 0.0006(6) 0.0062(6) -0.0008(6) C1 0.0208(8) 0.0225(7) 0.0202(8) -0.0012(6) 0.0061(7) 0.0007(6) C6 0.0181(8) 0.0236(7) 0.0140(7) 0.0010(6) 0.0047(6) 0.0028(6) C16 0.0230(9) 0.0229(8) 0.0241(8) 0.0038(6) 0.0101(7) -0.0005(6) C11 0.0199(8) 0.0174(7) 0.0178(8) 0.0001(6) 0.0062(6) 0.0006(6) C2 0.0223(9) 0.0304(9) 0.0271(9) -0.0039(7) 0.0121(7) 0.0036(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 O2 C12 1.216(2) . ? O1 C7 1.2219(19) . ? O3 C13 1.211(2) . ? N1 C13 1.387(2) . ? N1 C12 1.369(2) . ? N1 C14 1.456(2) . ? N2 C15 1.461(2) . ? N2 C8 1.455(2) . ? N2 C11 1.467(2) . ? C13 C10 1.521(2) . ? C4 C5 1.388(2) . ? C4 C3 1.388(2) . ? C5 C6 1.397(2) . ? C12 C9 1.517(2) . ? C10 C9 1.538(2) . ? C10 C11 1.550(2) . ? C17 C16 1.522(2) . ? C9 C8 1.552(2) . ? C3 C2 1.391(3) . ? C7 C8 1.534(2) . ? C7 C6 1.498(2) . ? C1 C6 1.398(2) . ? C1 C2 1.383(2) . ? C16 C11 1.525(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 C13 N1 C14 123.14(15) . . ? C12 N1 C13 113.52(13) . . ? C12 N1 C14 123.14(14) . . ? C15 N2 C11 116.44(12) . . ? C8 N2 C15 115.28(13) . . ? C8 N2 C11 108.76(12) . . ? O3 C13 N1 123.48(15) . . ? O3 C13 C10 127.83(15) . . ? N1 C13 C10 108.66(13) . . ? C5 C4 C3 120.17(15) . . ? C4 C5 C6 120.52(15) . . ? O2 C12 N1 125.06(15) . . ? O2 C12 C9 126.48(15) . . ? N1 C12 C9 108.46(13) . . ? C13 C10 C9 103.97(12) . . ? C13 C10 C11 115.07(13) . . ? C9 C10 C11 105.44(12) . . ? C12 C9 C10 105.26(13) . . ? C12 C9 C8 110.77(12) . . ? C10 C9 C8 105.66(12) . . ? C4 C3 C2 119.65(16) . . ? O1 C7 C8 120.74(15) . . ? O1 C7 C6 121.13(14) . . ? C6 C7 C8 118.13(13) . . ? N2 C8 C9 103.13(12) . . ? N2 C8 C7 116.98(12) . . ? C7 C8 C9 109.31(12) . . ? C2 C1 C6 120.54(15) . . ? C5 C6 C7 122.71(14) . . ? C5 C6 C1 118.79(15) . . ? C1 C6 C7 118.50(14) . . ? C17 C16 C11 112.60(14) . . ? N2 C11 C10 101.63(12) . . ? N2 C11 C16 112.57(13) . . ? C16 C11 C10 116.81(13) . . ? C1 C2 C3 120.29(16) . . ? loop_ _exptl_crystal_face_index_h _exptl_crystal_face_index_k _exptl_crystal_face_index_l _exptl_crystal_face_perp_dist _exptl_oxdiff_crystal_face_indexfrac_h _exptl_oxdiff_crystal_face_indexfrac_k _exptl_oxdiff_crystal_face_indexfrac_l _exptl_oxdiff_crystal_face_x _exptl_oxdiff_crystal_face_y _exptl_oxdiff_crystal_face_z 5 -4 2 0.1067 5.0522 -3.8056 1.7207 -0.7265 0.1159 0.6764 3 -5 -3 0.0855 3.3577 -5.1758 -3.4038 -0.0711 0.0190 0.9958 -2 -2 -7 0.1350 -2.4291 -1.7335 -6.9499 0.9037 -0.1339 0.4103 -4 5 1 0.1175 -4.3958 4.9178 1.2633 0.3822 -0.0656 -0.9202 2 2 7 0.0859 2.4877 1.6690 6.9349 -0.9090 0.1348 -0.3982 -5 -4 5 0.0280 -4.9491 -4.3525 4.5346 -0.1337 -0.9281 0.3464 -7 1 7 0.0341 -6.9294 0.7825 7.3372 -0.1247 -0.8055 -0.5796 3 5 -3 0.1111 3.3047 5.2896 -2.6855 0.1109 0.7910 -0.6003 7 0 -7 0.1173 7.0419 0.0984 -7.3279 0.1349 0.8827 0.4506 -2 -4 -5 0.1010 -2.0216 -4.0005 -4.9954 0.6080 -0.3318 0.6995 2 4 5 0.1010 2.0216 4.0005 4.9954 -0.6080 0.3318 -0.6995 -5 5 3 0.1141 -4.9951 4.9930 2.9935 0.2569 -0.1695 -1.0073 _database_code_depnum_ccdc_archive 'CCDC 948607'