# 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_an45 _database_code_depnum_ccdc_archive 'CCDC 890425' #TrackingRef 'web_deposit_cif_file_0_B.Sridhar_1341459968.an45f.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C18 H17 N O3' _chemical_formula_sum 'C18 H17 N O3' _chemical_formula_weight 295.33 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 orthorhombic _symmetry_space_group_name_H-M 'P bcn' _symmetry_space_group_name_Hall '-P 2n 2ab' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, -y+1/2, z+1/2' '-x, y, -z+1/2' 'x+1/2, -y+1/2, -z' '-x, -y, -z' 'x-1/2, y-1/2, -z-1/2' 'x, -y, z-1/2' '-x-1/2, y-1/2, z' _cell_length_a 18.360(3) _cell_length_b 10.7617(18) _cell_length_c 15.277(3) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 3018.5(9) _cell_formula_units_Z 8 _cell_measurement_temperature 294(2) _cell_measurement_reflns_used 8593 _cell_measurement_theta_min 2.19 _cell_measurement_theta_max 27.68 _exptl_crystal_description block _exptl_crystal_colour colorless _exptl_crystal_size_max 0.21 _exptl_crystal_size_mid 0.18 _exptl_crystal_size_min 0.08 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.300 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1248 _exptl_absorpt_coefficient_mu 0.089 _exptl_absorpt_correction_type none _exptl_absorpt_correction_T_min ? _exptl_absorpt_correction_T_max ? _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 294(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_device 'Bruker SMART APEX CCD area-detector' _diffrn_measurement_method '\w scan' _diffrn_detector_area_resol_mean ? _diffrn_standards_number 0 _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 27253 _diffrn_reflns_av_R_equivalents 0.0281 _diffrn_reflns_av_sigmaI/netI 0.0144 _diffrn_reflns_limit_h_min -21 _diffrn_reflns_limit_h_max 21 _diffrn_reflns_limit_k_min -12 _diffrn_reflns_limit_k_max 12 _diffrn_reflns_limit_l_min -18 _diffrn_reflns_limit_l_max 18 _diffrn_reflns_theta_min 2.19 _diffrn_reflns_theta_max 25.00 _reflns_number_total 2661 _reflns_number_gt 2219 _reflns_threshold_expression I>2\s(I) _computing_data_collection 'SMART (Bruker, 2001)' _computing_cell_refinement 'SAINT (Bruker, 2001)' _computing_data_reduction SAINT _computing_structure_solution 'SHELXS-97 (Sheldrick, 2008)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 2008)' _computing_molecular_graphics 'SHELXTL/PC (Sheldrick, 1990)' _computing_publication_material SHELXL97 _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^)+(0.0454P)^2^+0.5968P] 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 2661 _refine_ls_number_parameters 204 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0420 _refine_ls_R_factor_gt 0.0341 _refine_ls_wR_factor_ref 0.0972 _refine_ls_wR_factor_gt 0.0898 _refine_ls_goodness_of_fit_ref 1.053 _refine_ls_restrained_S_all 1.053 _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 0.32786(7) 0.16024(12) 0.10411(9) 0.0471(3) Uani 1 1 d . . . C2 C 0.39946(7) 0.19021(14) 0.08709(10) 0.0542(4) Uani 1 1 d . . . H2 H 0.4224 0.1578 0.0378 0.065 Uiso 1 1 calc R . . C3 C 0.43711(8) 0.26743(15) 0.14233(11) 0.0651(4) Uani 1 1 d . . . H3 H 0.4853 0.2882 0.1305 0.078 Uiso 1 1 calc R . . C4 C 0.40296(8) 0.31381(16) 0.21527(11) 0.0644(4) Uani 1 1 d . . . H4 H 0.4283 0.3659 0.2531 0.077 Uiso 1 1 calc R . . C5 C 0.33166(8) 0.28393(14) 0.23295(10) 0.0574(4) Uani 1 1 d . . . H5 H 0.3094 0.3159 0.2828 0.069 Uiso 1 1 calc R . . C6 C 0.29262(7) 0.20686(13) 0.17759(9) 0.0485(3) Uani 1 1 d . . . C7 C 0.18213(7) 0.10204(13) 0.13178(9) 0.0517(4) Uani 1 1 d . . . H7 H 0.1466 0.0499 0.1625 0.062 Uiso 1 1 calc R . . C8 C 0.23234(7) 0.01717(13) 0.08024(10) 0.0560(4) Uani 1 1 d . . . H8 H 0.2489 -0.0537 0.1153 0.067 Uiso 1 1 calc R . . C9 C 0.18700(8) -0.02332(14) 0.00370(11) 0.0627(4) Uani 1 1 d . . . H9A H 0.2175 -0.0428 -0.0462 0.075 Uiso 1 1 calc R . . H9B H 0.1582 -0.0959 0.0185 0.075 Uiso 1 1 calc R . . C10 C 0.13884(7) 0.08583(14) -0.01567(10) 0.0535(4) Uani 1 1 d . . . C11 C 0.14119(7) 0.17607(13) 0.06124(9) 0.0488(3) Uani 1 1 d . . . H11 H 0.1719 0.2466 0.0443 0.059 Uiso 1 1 calc R . . C12 C 0.06871(7) 0.22650(12) 0.08965(9) 0.0477(3) Uani 1 1 d . . . C13 C 0.01222(7) 0.14668(13) 0.11137(10) 0.0537(4) Uani 1 1 d . . . H13 H 0.0188 0.0614 0.1053 0.064 Uiso 1 1 calc R . . C14 C -0.05298(8) 0.19072(14) 0.14153(9) 0.0547(4) Uani 1 1 d . . . H14 H -0.0901 0.1354 0.1557 0.066 Uiso 1 1 calc R . . C15 C -0.06394(7) 0.31661(14) 0.15096(9) 0.0521(3) Uani 1 1 d . . . C16 C -0.00907(8) 0.39769(14) 0.12926(10) 0.0580(4) Uani 1 1 d . . . H16 H -0.0160 0.4829 0.1351 0.070 Uiso 1 1 calc R . . C17 C 0.05652(8) 0.35182(13) 0.09876(10) 0.0544(4) Uani 1 1 d . . . H17 H 0.0934 0.4073 0.0840 0.065 Uiso 1 1 calc R . . C18 C -0.14560(10) 0.47991(18) 0.18717(14) 0.0858(6) Uani 1 1 d . . . H18A H -0.1124 0.5171 0.2280 0.129 Uiso 1 1 calc R . . H18B H -0.1947 0.4923 0.2070 0.129 Uiso 1 1 calc R . . H18C H -0.1395 0.5177 0.1307 0.129 Uiso 1 1 calc R . . N1 N 0.22173(7) 0.17089(14) 0.19594(9) 0.0621(4) Uani 1 1 d . . . O1 O 0.29221(5) 0.08613(9) 0.04469(6) 0.0562(3) Uani 1 1 d . . . O2 O 0.10378(7) 0.09950(12) -0.08076(8) 0.0779(4) Uani 1 1 d . . . O3 O -0.13113(6) 0.35101(11) 0.18096(7) 0.0681(3) Uani 1 1 d . . . H1N H 0.1978(9) 0.2174(15) 0.2324(12) 0.070(5) Uiso 1 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 0.0411(7) 0.0493(7) 0.0509(7) 0.0043(6) -0.0040(6) 0.0042(6) C2 0.0429(7) 0.0613(8) 0.0584(8) 0.0082(7) 0.0030(6) 0.0038(7) C3 0.0431(8) 0.0762(11) 0.0761(11) 0.0074(9) -0.0052(8) -0.0081(7) C4 0.0521(9) 0.0699(10) 0.0713(10) -0.0023(8) -0.0172(8) -0.0034(8) C5 0.0519(8) 0.0659(9) 0.0542(8) -0.0023(7) -0.0092(7) 0.0085(7) C6 0.0383(7) 0.0567(8) 0.0506(7) 0.0057(6) -0.0042(6) 0.0063(6) C7 0.0384(7) 0.0580(8) 0.0587(8) 0.0058(7) 0.0020(6) -0.0028(6) C8 0.0467(8) 0.0515(8) 0.0698(9) 0.0036(7) -0.0003(7) 0.0005(6) C9 0.0560(8) 0.0530(9) 0.0790(10) -0.0083(8) -0.0018(8) -0.0050(7) C10 0.0428(7) 0.0595(9) 0.0581(9) 0.0028(7) 0.0021(7) -0.0079(6) C11 0.0395(7) 0.0481(7) 0.0587(8) 0.0038(6) 0.0019(6) -0.0062(6) C12 0.0409(7) 0.0504(8) 0.0519(7) 0.0009(6) -0.0035(6) -0.0024(6) C13 0.0452(8) 0.0471(7) 0.0686(9) -0.0010(7) 0.0003(7) -0.0022(6) C14 0.0431(7) 0.0591(9) 0.0619(9) -0.0006(7) 0.0024(6) -0.0060(6) C15 0.0438(7) 0.0657(9) 0.0469(7) -0.0053(6) -0.0006(6) 0.0035(7) C16 0.0568(9) 0.0501(8) 0.0670(9) -0.0067(7) -0.0011(7) 0.0029(7) C17 0.0468(8) 0.0510(8) 0.0653(9) 0.0003(7) -0.0014(7) -0.0063(6) C18 0.0736(12) 0.0847(13) 0.0991(14) -0.0159(11) 0.0128(10) 0.0241(10) N1 0.0409(7) 0.0874(10) 0.0581(7) -0.0130(7) 0.0020(6) 0.0031(6) O1 0.0441(5) 0.0653(6) 0.0593(6) -0.0079(5) 0.0028(4) -0.0027(5) O2 0.0779(8) 0.0955(9) 0.0604(7) -0.0043(6) -0.0110(6) 0.0100(7) O3 0.0535(6) 0.0778(7) 0.0729(7) -0.0071(6) 0.0112(5) 0.0109(5) _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 O1 1.3742(16) . ? C1 C2 1.3783(19) . ? C1 C6 1.3894(19) . ? C2 C3 1.371(2) . ? C2 H2 0.9300 . ? C3 C4 1.373(2) . ? C3 H3 0.9300 . ? C4 C5 1.375(2) . ? C4 H4 0.9300 . ? C5 C6 1.385(2) . ? C5 H5 0.9300 . ? C6 N1 1.3864(18) . ? C7 N1 1.4277(19) . ? C7 C8 1.518(2) . ? C7 C11 1.5366(19) . ? C7 H7 0.9800 . ? C8 O1 1.4332(16) . ? C8 C9 1.500(2) . ? C8 H8 0.9800 . ? C9 C10 1.500(2) . ? C9 H9A 0.9700 . ? C9 H9B 0.9700 . ? C10 O2 1.1936(17) . ? C10 C11 1.525(2) . ? C11 C12 1.5012(19) . ? C11 H11 0.9800 . ? C12 C17 1.374(2) . ? C12 C13 1.3869(19) . ? C13 C14 1.368(2) . ? C13 H13 0.9300 . ? C14 C15 1.377(2) . ? C14 H14 0.9300 . ? C15 O3 1.3672(17) . ? C15 C16 1.373(2) . ? C16 C17 1.382(2) . ? C16 H16 0.9300 . ? C17 H17 0.9300 . ? C18 O3 1.416(2) . ? C18 H18A 0.9600 . ? C18 H18B 0.9600 . ? C18 H18C 0.9600 . ? N1 H1N 0.869(18) . ? 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 O1 C1 C2 117.74(12) . . ? O1 C1 C6 121.43(12) . . ? C2 C1 C6 120.80(13) . . ? C3 C2 C1 120.43(14) . . ? C3 C2 H2 119.8 . . ? C1 C2 H2 119.8 . . ? C2 C3 C4 119.32(14) . . ? C2 C3 H3 120.3 . . ? C4 C3 H3 120.3 . . ? C3 C4 C5 120.63(15) . . ? C3 C4 H4 119.7 . . ? C5 C4 H4 119.7 . . ? C4 C5 C6 120.87(15) . . ? C4 C5 H5 119.6 . . ? C6 C5 H5 119.6 . . ? C5 C6 N1 121.99(13) . . ? C5 C6 C1 117.95(13) . . ? N1 C6 C1 119.98(13) . . ? N1 C7 C8 111.04(11) . . ? N1 C7 C11 117.49(12) . . ? C8 C7 C11 104.19(12) . . ? N1 C7 H7 107.9 . . ? C8 C7 H7 107.9 . . ? C11 C7 H7 107.9 . . ? O1 C8 C9 106.30(12) . . ? O1 C8 C7 110.53(11) . . ? C9 C8 C7 104.01(11) . . ? O1 C8 H8 111.9 . . ? C9 C8 H8 111.9 . . ? C7 C8 H8 111.9 . . ? C10 C9 C8 104.69(12) . . ? C10 C9 H9A 110.8 . . ? C8 C9 H9A 110.8 . . ? C10 C9 H9B 110.8 . . ? C8 C9 H9B 110.8 . . ? H9A C9 H9B 108.9 . . ? O2 C10 C9 125.37(14) . . ? O2 C10 C11 125.35(14) . . ? C9 C10 C11 109.28(12) . . ? C12 C11 C10 115.34(11) . . ? C12 C11 C7 114.72(11) . . ? C10 C11 C7 102.95(11) . . ? C12 C11 H11 107.8 . . ? C10 C11 H11 107.8 . . ? C7 C11 H11 107.8 . . ? C17 C12 C13 117.50(13) . . ? C17 C12 C11 121.90(12) . . ? C13 C12 C11 120.54(12) . . ? C14 C13 C12 121.37(13) . . ? C14 C13 H13 119.3 . . ? C12 C13 H13 119.3 . . ? C13 C14 C15 120.27(13) . . ? C13 C14 H14 119.9 . . ? C15 C14 H14 119.9 . . ? O3 C15 C16 124.80(14) . . ? O3 C15 C14 115.67(13) . . ? C16 C15 C14 119.51(13) . . ? C15 C16 C17 119.57(13) . . ? C15 C16 H16 120.2 . . ? C17 C16 H16 120.2 . . ? C12 C17 C16 121.77(13) . . ? C12 C17 H17 119.1 . . ? C16 C17 H17 119.1 . . ? O3 C18 H18A 109.5 . . ? O3 C18 H18B 109.5 . . ? H18A C18 H18B 109.5 . . ? O3 C18 H18C 109.5 . . ? H18A C18 H18C 109.5 . . ? H18B C18 H18C 109.5 . . ? C6 N1 C7 118.97(13) . . ? C6 N1 H1N 116.4(11) . . ? C7 N1 H1N 118.8(11) . . ? C1 O1 C8 114.56(10) . . ? C15 O3 C18 117.20(13) . . ? 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 O1 C1 C2 C3 177.66(13) . . . . ? C6 C1 C2 C3 -0.4(2) . . . . ? C1 C2 C3 C4 0.6(2) . . . . ? C2 C3 C4 C5 -0.3(2) . . . . ? C3 C4 C5 C6 -0.2(2) . . . . ? C4 C5 C6 N1 177.09(14) . . . . ? C4 C5 C6 C1 0.4(2) . . . . ? O1 C1 C6 C5 -178.07(12) . . . . ? C2 C1 C6 C5 -0.1(2) . . . . ? O1 C1 C6 N1 5.2(2) . . . . ? C2 C1 C6 N1 -176.85(13) . . . . ? N1 C7 C8 O1 -53.06(16) . . . . ? C11 C7 C8 O1 74.34(13) . . . . ? N1 C7 C8 C9 -166.79(12) . . . . ? C11 C7 C8 C9 -39.39(14) . . . . ? O1 C8 C9 C10 -83.86(13) . . . . ? C7 C8 C9 C10 32.86(15) . . . . ? C8 C9 C10 O2 166.23(15) . . . . ? C8 C9 C10 C11 -14.27(15) . . . . ? O2 C10 C11 C12 44.1(2) . . . . ? C9 C10 C11 C12 -135.40(12) . . . . ? O2 C10 C11 C7 169.81(14) . . . . ? C9 C10 C11 C7 -9.68(14) . . . . ? N1 C7 C11 C12 -80.88(15) . . . . ? C8 C7 C11 C12 155.81(11) . . . . ? N1 C7 C11 C10 153.01(12) . . . . ? C8 C7 C11 C10 29.70(13) . . . . ? C10 C11 C12 C17 -127.98(14) . . . . ? C7 C11 C12 C17 112.62(15) . . . . ? C10 C11 C12 C13 54.80(18) . . . . ? C7 C11 C12 C13 -64.60(17) . . . . ? C17 C12 C13 C14 -0.6(2) . . . . ? C11 C12 C13 C14 176.72(13) . . . . ? C12 C13 C14 C15 0.1(2) . . . . ? C13 C14 C15 O3 179.55(13) . . . . ? C13 C14 C15 C16 0.4(2) . . . . ? O3 C15 C16 C17 -179.38(13) . . . . ? C14 C15 C16 C17 -0.4(2) . . . . ? C13 C12 C17 C16 0.7(2) . . . . ? C11 C12 C17 C16 -176.59(13) . . . . ? C15 C16 C17 C12 -0.2(2) . . . . ? C5 C6 N1 C7 173.55(13) . . . . ? C1 C6 N1 C7 -9.8(2) . . . . ? C8 C7 N1 C6 33.51(18) . . . . ? C11 C7 N1 C6 -86.24(16) . . . . ? C2 C1 O1 C8 155.19(12) . . . . ? C6 C1 O1 C8 -26.76(17) . . . . ? C9 C8 O1 C1 162.19(11) . . . . ? C7 C8 O1 C1 49.92(15) . . . . ? C16 C15 O3 C18 2.2(2) . . . . ? C14 C15 O3 C18 -176.84(15) . . . . ? loop_ _geom_hbond_atom_site_label_D _geom_hbond_atom_site_label_H _geom_hbond_atom_site_label_A _geom_hbond_distance_DH _geom_hbond_distance_HA _geom_hbond_distance_DA _geom_hbond_angle_DHA _geom_hbond_site_symmetry_A N1 H1N O3 0.869(18) 2.306(18) 3.1719(19) 175.1(16) 3 _diffrn_measured_fraction_theta_max 1.000 _diffrn_reflns_theta_full 25.00 _diffrn_measured_fraction_theta_full 1.000 _refine_diff_density_max 0.163 _refine_diff_density_min -0.140 _refine_diff_density_rms 0.027