# Electronic Supplementary Material (ESI) for RSC Advances. # This journal is © The Royal Society of Chemistry 2019 ####################################################################### # # This file contains crystal structure data downloaded from the # Cambridge Structural Database (CSD) hosted by the Cambridge # Crystallographic Data Centre (CCDC). # # Full information about CCDC data access policies and citation # guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 # # Audit and citation data items may have been added by the CCDC. # Please retain this information to preserve the provenance of # this file and to allow appropriate attribution of the data. # ####################################################################### data_lborg1 _database_code_depnum_ccdc_archive 'CCDC 1883868' loop_ _audit_author_name _audit_author_address 'LEONI A. BARRIOS' ;UNIVERSITY OF BARCELONA Spain ; _audit_update_record ; 2018-12-07 deposited with the CCDC. 2019-08-01 downloaded from the CCDC. ; _audit_creation_date 2018-12-07 _audit_creation_method ; Olex2 1.2 (compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506) ; _shelx_SHELXL_version_number 2018/3 _chemical_name_common ? _chemical_name_systematic INDOLINE _chemical_formula_moiety 'C18 H18 N2 O3' _chemical_formula_sum 'C18 H18 N2 O3' _chemical_formula_weight 310.34 _chemical_melting_point ? 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' _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 9.7644(15) _cell_length_b 12.097(2) _cell_length_c 13.137(2) _cell_angle_alpha 90.00 _cell_angle_beta 94.859(11) _cell_angle_gamma 90.00 _cell_volume 1546.1(5) _cell_formula_units_Z 4 _cell_measurement_reflns_used 1270 _cell_measurement_temperature 100(2) _cell_measurement_theta_max 21.58 _cell_measurement_theta_min 2.69 _exptl_absorpt_coefficient_mu 0.092 _exptl_absorpt_correction_T_max 0.7447 _exptl_absorpt_correction_T_min 0.5054 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details 'SADABS-2008/1 (Bruker,2008) was used for absorption correction. wR2(int) was 0.1637 before and 0.0749 after correction. The Ratio of minimum to maximum transmission is 0.6787. The \l/2 correction factor is 0.0015.' _exptl_crystal_colour 'clear whiteish white' _exptl_crystal_colour_lustre clear _exptl_crystal_colour_modifier whiteish _exptl_crystal_colour_primary white _exptl_crystal_density_diffrn 1.333 _exptl_crystal_density_meas ? _exptl_crystal_density_method ? _exptl_crystal_description needle _exptl_crystal_F_000 656 _exptl_crystal_size_max 0.117 _exptl_crystal_size_mid 0.085 _exptl_crystal_size_min 0.017 _exptl_special_details ; ? ; _diffrn_reflns_av_R_equivalents 0.0758 _diffrn_reflns_av_unetI/netI 0.0760 _diffrn_reflns_limit_h_max 10 _diffrn_reflns_limit_h_min -10 _diffrn_reflns_limit_k_max 12 _diffrn_reflns_limit_k_min -11 _diffrn_reflns_limit_l_max 13 _diffrn_reflns_limit_l_min -13 _diffrn_reflns_number 6728 _diffrn_reflns_theta_full 25.027 _diffrn_reflns_theta_max 25.027 _diffrn_reflns_theta_min 1.761 _diffrn_ambient_temperature 100.0 _diffrn_detector_area_resol_mean ? _diffrn_measured_fraction_theta_full 0.995 _diffrn_measured_fraction_theta_max 0.995 _diffrn_measurement_device_type 'Bruker APEX-II CCD' _diffrn_measurement_method '\f and \w scans' _diffrn_radiation_monochromator graphite _diffrn_radiation_type MoK\a _diffrn_radiation_wavelength 0.71073 _diffrn_source 'fine-focus sealed tube' _diffrn_standards_number 0 _reflns_number_gt 1420 _reflns_number_total 1886 _reflns_threshold_expression >2sigma(I) _computing_cell_refinement 'SAINT v8.34A (Bruker, 2013)' _computing_data_collection ? _computing_data_reduction 'SAINT v8.34A (Bruker, 2013)' _computing_molecular_graphics 'Olex2 (Dolomanov et al., 2009)' _computing_publication_material 'Olex2 (Dolomanov et al., 2009)' _computing_structure_refinement 'XL (Sheldrick, 2008)' _computing_structure_solution 'XS (Sheldrick, 2008)' _refine_diff_density_max 0.396 _refine_diff_density_min -0.458 _refine_diff_density_rms 0.143 _refine_ls_extinction_coef ? _refine_ls_extinction_method none _refine_ls_goodness_of_fit_ref 1.109 _refine_ls_hydrogen_treatment constr _refine_ls_matrix_type full _refine_ls_number_parameters 221 _refine_ls_number_reflns 1886 _refine_ls_number_restraints 233 _refine_ls_R_factor_all 0.0873 _refine_ls_R_factor_gt 0.0617 _refine_ls_restrained_S_all 1.042 _refine_ls_shift/su_max 0.000 _refine_ls_shift/su_mean 0.000 _refine_ls_structure_factor_coef Fsqd _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.1110P)^2^+0.0290P] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_gt 0.1688 _refine_ls_wR_factor_ref 0.1920 _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. Rigid bond restraints All non-hydrogen atoms with sigma for 1-2 distances of 0.01 and sigma for 1-3 distances of 0.01 3. Uiso/Uaniso restraints and constraints All non-hydrogen atoms have similar U: within 1.7A with sigma of 0.04 and sigma for terminal atoms of 0.08 Uanis(N1) \\sim Ueq: with sigma of 0.1 and sigma for terminal atoms of 0.2 4. Others Sof(O1A)=1-FVAR(1) Sof(O1)=FVAR(1) 5.a Secondary CH2 refined with riding coordinates: C8(H8a,H8b) 5.b Aromatic/amide H refined with riding coordinates: C4(H4), C5(H5), C6(H6), C12(H12), C13(H13), C14(H14), C15(H15) 5.c Idealised Me refined as rotating group: C16(H16a,H16b,H16c), C17(H17a,H17b,H17c), C19(H19a,H19b,H19c) ; _atom_sites_solution_hydrogens geom _atom_sites_solution_primary direct _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_calc_flag _atom_site_disorder_assembly _atom_site_disorder_group _atom_site_refinement_flags_posn _atom_site_refinement_flags_adp C2 C 0.1203(3) 0.2907(3) 0.8481(3) 0.0203(9) Uani 1 d . . . U C3 C 0.1368(3) 0.3914(3) 0.8974(3) 0.0192(9) Uani 1 d . . . U C4 C 0.1709(3) 0.3971(3) 1.0017(3) 0.0215(9) Uani 1 d . . . U H4 H 0.1763 0.4662 1.0362 0.026 Uiso 1 calc . . R . C5 C 0.1972(4) 0.2987(3) 1.0547(3) 0.0244(10) Uani 1 d . . . U H5 H 0.2221 0.3011 1.1261 0.029 Uiso 1 calc . . R . C6 C 0.1876(4) 0.1971(3) 1.0053(3) 0.0247(10) Uani 1 d . . . U H6 H 0.2070 0.1305 1.0421 0.030 Uiso 1 calc . . R . C7 C 0.1497(4) 0.1946(3) 0.9024(3) 0.0235(9) Uani 1 d . . . U C8 C 0.0707(4) 0.3072(3) 0.7378(3) 0.0245(10) Uani 1 d . . . U H8A H -0.0025 0.2536 0.7159 0.029 Uiso 1 calc . . R . H8B H 0.1470 0.2994 0.6933 0.029 Uiso 1 calc . . R . C9 C 0.0148(4) 0.4261(3) 0.7352(3) 0.0213(9) Uani 1 d . . . U C10 C 0.1118(4) 0.5886(3) 0.8389(3) 0.0217(9) Uani 1 d . . . U C11 C 0.2188(4) 0.6313(3) 0.9177(3) 0.0220(9) Uani 1 d . . . U C12 C 0.1878(4) 0.7200(3) 0.9788(3) 0.0245(10) Uani 1 d . . . U H12 H 0.0979 0.7505 0.9742 0.029 Uiso 1 calc . . R . C13 C 0.2911(4) 0.7633(3) 1.0468(3) 0.0269(10) Uani 1 d . . . U H13 H 0.2724 0.8228 1.0908 0.032 Uiso 1 calc . . R . C14 C 0.4211(4) 0.7184(3) 1.0493(3) 0.0279(10) Uani 1 d . . . U H14 H 0.4942 0.7471 1.0939 0.033 Uiso 1 calc . . R . C15 C 0.4426(4) 0.6305(3) 0.9852(3) 0.0271(10) Uani 1 d . . . U H15 H 0.5324 0.5998 0.9874 0.033 Uiso 1 calc . . R . C16 C 0.0342(4) 0.4810(3) 0.6339(2) 0.0276(10) Uani 1 d . . . U H16A H -0.0149 0.5518 0.6299 0.041 Uiso 1 calc . . GR . H16B H -0.0024 0.4329 0.5780 0.041 Uiso 1 calc . . GR . H16C H 0.1323 0.4939 0.6281 0.041 Uiso 1 calc . . GR . C17 C -0.1374(4) 0.4269(3) 0.7576(3) 0.0263(10) Uani 1 d . . . U H17A H -0.1476 0.3885 0.8222 0.039 Uiso 1 calc . . GR . H17B H -0.1924 0.3893 0.7021 0.039 Uiso 1 calc . . GR . H17C H -0.1689 0.5035 0.7626 0.039 Uiso 1 calc . . GR . C18 C 0.0248(4) 0.0361(3) 0.8388(3) 0.0362(11) Uani 1 d . . . U C19 C 0.0379(4) -0.0672(3) 0.7793(3) 0.0334(11) Uani 1 d A . . U H19A H 0.0766 -0.0499 0.7147 0.050 Uiso 1 calc . . GR . H19B H -0.0529 -0.1009 0.7652 0.050 Uiso 1 calc . . GR . H19C H 0.0988 -0.1188 0.8188 0.050 Uiso 1 calc . . GR . N1 N 0.0984(3) 0.4769(2) 0.8253(2) 0.0202(8) Uani 1 d . . . U N2 N 0.3450(3) 0.5860(2) 0.9203(2) 0.0247(8) Uani 1 d . . . U O1 O -0.0730(19) 0.060(2) 0.887(3) 0.051(4) Uani 0.59(10) d A 1 . U O2 O 0.1451(2) 0.0926(2) 0.84990(18) 0.0268(7) Uani 1 d A . . U O3 O 0.0430(2) 0.6552(2) 0.78524(18) 0.0272(7) Uani 1 d . . . U O1A O -0.080(2) 0.089(4) 0.844(7) 0.064(12) Uani 0.41(10) d A 2 . U 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 C2 0.0105(19) 0.028(2) 0.0224(19) 0.0002(17) -0.0004(16) -0.0024(17) C3 0.0099(19) 0.022(2) 0.0255(19) 0.0017(17) 0.0003(16) -0.0024(17) C4 0.015(2) 0.021(2) 0.028(2) -0.0034(18) 0.0006(17) 0.0005(17) C5 0.014(2) 0.033(3) 0.025(2) -0.0016(18) 0.0001(17) -0.0017(18) C6 0.018(2) 0.024(2) 0.031(2) 0.0053(18) -0.0016(18) 0.0018(18) C7 0.017(2) 0.019(2) 0.034(2) -0.0028(18) 0.0008(17) -0.0006(17) C8 0.021(2) 0.026(2) 0.026(2) -0.0017(17) 0.0005(17) -0.0001(17) C9 0.022(2) 0.020(2) 0.0217(19) -0.0039(16) -0.0026(16) 0.0000(17) C10 0.017(2) 0.022(2) 0.026(2) -0.0021(18) 0.0035(17) -0.0024(18) C11 0.018(2) 0.020(2) 0.028(2) 0.0012(17) 0.0027(16) 0.0002(17) C12 0.020(2) 0.023(2) 0.031(2) 0.0021(18) 0.0043(17) -0.0024(18) C13 0.026(2) 0.025(2) 0.029(2) -0.0044(19) 0.0029(18) -0.0073(19) C14 0.025(2) 0.027(2) 0.031(2) 0.0016(18) -0.0029(18) -0.0048(19) C15 0.021(2) 0.024(2) 0.036(2) 0.0053(19) -0.0026(18) -0.0019(18) C16 0.032(2) 0.025(2) 0.025(2) -0.0012(18) 0.0015(18) -0.0005(19) C17 0.021(2) 0.028(2) 0.029(2) 0.0018(18) -0.0037(17) 0.0003(17) C18 0.027(3) 0.031(3) 0.049(3) -0.005(2) 0.001(2) -0.002(2) C19 0.033(3) 0.022(2) 0.045(2) -0.0031(19) 0.005(2) -0.0063(19) N1 0.0174(18) 0.0193(18) 0.0233(16) 0.0001(14) -0.0025(13) -0.0021(14) N2 0.0194(19) 0.0223(19) 0.0322(18) 0.0020(15) 0.0012(15) -0.0022(15) O1 0.037(5) 0.036(8) 0.084(10) -0.020(7) 0.031(5) -0.009(5) O2 0.0203(15) 0.0209(16) 0.0394(15) -0.0038(12) 0.0039(12) -0.0010(12) O3 0.0247(16) 0.0212(16) 0.0345(15) -0.0010(13) -0.0040(12) 0.0058(12) O1A 0.017(5) 0.042(12) 0.13(3) -0.040(16) 0.019(11) -0.016(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 C2 C3 1.383(5) . ? C2 C7 1.381(5) . ? C2 C8 1.501(5) . ? C3 C4 1.384(5) . ? C3 N1 1.431(4) . ? C4 C5 1.391(5) . ? C5 C6 1.390(5) . ? C6 C7 1.371(5) . ? C7 O2 1.413(4) . ? C8 C9 1.538(5) . ? C9 C16 1.514(5) . ? C9 C17 1.539(5) . ? C9 N1 1.510(5) . ? C10 C11 1.500(5) . ? C10 N1 1.367(5) . ? C10 O3 1.231(4) . ? C11 C12 1.388(5) . ? C11 N2 1.346(4) . ? C12 C13 1.393(5) . ? C13 C14 1.378(5) . ? C14 C15 1.384(5) . ? C15 N2 1.337(5) . ? C18 C19 1.485(5) . ? C18 O1 1.229(16) . ? C18 O2 1.356(5) . ? C18 O1A 1.21(3) . ? 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 C3 C2 C8 110.5(3) . . ? C7 C2 C3 119.2(3) . . ? C7 C2 C8 130.3(3) . . ? C2 C3 C4 121.1(3) . . ? C2 C3 N1 108.2(3) . . ? C4 C3 N1 130.3(3) . . ? C3 C4 C5 118.1(3) . . ? C6 C5 C4 121.4(3) . . ? C7 C6 C5 118.8(3) . . ? C2 C7 O2 119.1(3) . . ? C6 C7 C2 121.2(3) . . ? C6 C7 O2 119.7(3) . . ? C2 C8 C9 103.3(3) . . ? C8 C9 C17 110.4(3) . . ? C16 C9 C8 111.1(3) . . ? C16 C9 C17 111.0(3) . . ? N1 C9 C8 101.3(3) . . ? N1 C9 C16 114.3(3) . . ? N1 C9 C17 108.3(3) . . ? N1 C10 C11 118.9(3) . . ? O3 C10 C11 119.0(3) . . ? O3 C10 N1 122.0(3) . . ? C12 C11 C10 119.5(3) . . ? N2 C11 C10 117.4(3) . . ? N2 C11 C12 122.9(3) . . ? C11 C12 C13 118.7(3) . . ? C14 C13 C12 118.8(4) . . ? C13 C14 C15 118.4(4) . . ? N2 C15 C14 124.1(4) . . ? O1 C18 C19 125.3(10) . . ? O1 C18 O2 122.0(8) . . ? O2 C18 C19 111.6(3) . . ? O1A C18 C19 125.9(15) . . ? O1A C18 O1 32(3) . . ? O1A C18 O2 117.0(16) . . ? C3 N1 C9 108.5(3) . . ? C10 N1 C3 127.7(3) . . ? C10 N1 C9 122.9(3) . . ? C15 N2 C11 117.0(3) . . ? C18 O2 C7 119.0(3) . . ? _olex2_submission_special_instructions 'No special instructions were received'