# 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_5f _database_code_depnum_ccdc_archive 'CCDC 901326' _audit_creation_method SHELXL-97 _chemical_name_systematic ; tert-butyl 2-(furan-2-carbonyl)indoline-1-carboxylate ; _chemical_name_common ? _chemical_melting_point 386 _chemical_formula_moiety 'C18 H19 N O4' _chemical_formula_sum 'C18 H19 N O4' _chemical_formula_weight 313.34 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 P2(1)/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 14.325(5) _cell_length_b 7.607(2) _cell_length_c 16.273(6) _cell_angle_alpha 90.00 _cell_angle_beta 106.477(7) _cell_angle_gamma 90.00 _cell_volume 1700.4(10) _cell_formula_units_Z 4 _cell_measurement_temperature 113(2) _cell_measurement_reflns_used 5309 _cell_measurement_theta_min 1.5 _cell_measurement_theta_max 27.9 _exptl_crystal_description Prism _exptl_crystal_colour Colorless _exptl_crystal_size_max 0.14 _exptl_crystal_size_mid 0.12 _exptl_crystal_size_min 0.06 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.224 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 664 _exptl_absorpt_coefficient_mu 0.087 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.9880 _exptl_absorpt_correction_T_max 0.9948 _exptl_absorpt_process_details CrystalClear _exptl_special_details ; ? ; _diffrn_ambient_temperature 113(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'rotating anode' _diffrn_radiation_monochromator multilayer _diffrn_measurement_device_type 'Rigaku Saturn724 CCD' _diffrn_measurement_method '\w and \f scans' _diffrn_detector_area_resol_mean 14.22 _diffrn_standards_number 0 _diffrn_standards_interval_count 0 _diffrn_standards_interval_time 0 _diffrn_standards_decay_% 0 _diffrn_reflns_number 17109 _diffrn_reflns_av_R_equivalents 0.0436 _diffrn_reflns_av_sigmaI/netI 0.0450 _diffrn_reflns_limit_h_min -18 _diffrn_reflns_limit_h_max 18 _diffrn_reflns_limit_k_min -9 _diffrn_reflns_limit_k_max 9 _diffrn_reflns_limit_l_min -21 _diffrn_reflns_limit_l_max 21 _diffrn_reflns_theta_min 1.48 _diffrn_reflns_theta_max 27.88 _reflns_number_total 4041 _reflns_number_gt 3068 _reflns_threshold_expression >2sigma(I) _computing_data_collection CrystalClear _computing_cell_refinement CrystalClear _computing_data_reduction CrystalClear _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Bruker SHELXTL' _computing_publication_material 'CrystalStructure 3.8' _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^)+(0.0512P)^2^+0.0000P] 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 4041 _refine_ls_number_parameters 211 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0706 _refine_ls_R_factor_gt 0.0497 _refine_ls_wR_factor_ref 0.1141 _refine_ls_wR_factor_gt 0.1036 _refine_ls_goodness_of_fit_ref 1.039 _refine_ls_restrained_S_all 1.039 _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 O1 O 0.43267(7) 0.28205(12) 0.18959(6) 0.0317(3) Uani 1 1 d . . . O2 O 0.33428(8) -0.02898(13) 0.15109(7) 0.0414(3) Uani 1 1 d . . . O3 O 0.16902(7) -0.30684(13) -0.05156(6) 0.0356(3) Uani 1 1 d . . . O4 O 0.25096(7) -0.05000(14) -0.05290(6) 0.0362(3) Uani 1 1 d . . . N1 N 0.15770(8) -0.07411(15) 0.03372(7) 0.0275(3) Uani 1 1 d . . . C1 C 0.46073(11) 0.45248(19) 0.19420(10) 0.0339(4) Uani 1 1 d . . . H1 H 0.5215 0.4948 0.2289 0.041 Uiso 1 1 calc R . . C2 C 0.39136(11) 0.5538(2) 0.14326(10) 0.0368(4) Uani 1 1 d . . . H2 H 0.3939 0.6774 0.1357 0.044 Uiso 1 1 calc R . . C3 C 0.31340(11) 0.43978(19) 0.10286(9) 0.0342(4) Uani 1 1 d . . . H3 H 0.2537 0.4721 0.0627 0.041 Uiso 1 1 calc R . . C4 C 0.34071(10) 0.27599(18) 0.13273(8) 0.0260(3) Uani 1 1 d . . . C5 C 0.29399(10) 0.10575(19) 0.11870(9) 0.0283(3) Uani 1 1 d . . . C6 C 0.18740(10) 0.10473(18) 0.06404(9) 0.0278(3) Uani 1 1 d . . . H6 H 0.1778 0.1874 0.0145 0.033 Uiso 1 1 calc R . . C7 C 0.11970(10) 0.15422(19) 0.11961(9) 0.0327(3) Uani 1 1 d . . . H7A H 0.1580 0.1930 0.1774 0.039 Uiso 1 1 calc R . . H7B H 0.0742 0.2492 0.0923 0.039 Uiso 1 1 calc R . . C8 C 0.06576(10) -0.01304(18) 0.12432(8) 0.0275(3) Uani 1 1 d . . . C9 C -0.00247(10) -0.0476(2) 0.16782(9) 0.0330(4) Uani 1 1 d . . . H9 H -0.0207 0.0414 0.2013 0.040 Uiso 1 1 calc R . . C10 C -0.04377(11) -0.2131(2) 0.16197(9) 0.0355(4) Uani 1 1 d . . . H10 H -0.0916 -0.2372 0.1906 0.043 Uiso 1 1 calc R . . C11 C -0.01585(10) -0.3441(2) 0.11464(9) 0.0333(4) Uani 1 1 d . . . H11 H -0.0434 -0.4581 0.1126 0.040 Uiso 1 1 calc R . . C12 C 0.05209(10) -0.31092(19) 0.06990(8) 0.0295(3) Uani 1 1 d . . . H12 H 0.0711 -0.4004 0.0372 0.035 Uiso 1 1 calc R . . C13 C 0.09100(9) -0.14326(18) 0.07469(8) 0.0260(3) Uani 1 1 d . . . C14 C 0.19117(10) -0.1586(2) -0.02648(9) 0.0296(3) Uani 1 1 d . . . C15 C 0.30532(11) -0.1113(2) -0.11273(10) 0.0439(4) Uani 1 1 d . . . C16 C 0.23564(13) -0.1569(3) -0.19891(10) 0.0565(5) Uani 1 1 d . . . H16A H 0.1948 -0.2563 -0.1924 0.085 Uiso 1 1 calc R . . H16B H 0.2727 -0.1887 -0.2389 0.085 Uiso 1 1 calc R . . H16C H 0.1942 -0.0551 -0.2212 0.085 Uiso 1 1 calc R . . C17 C 0.36427(14) 0.0515(3) -0.11948(13) 0.0679(6) Uani 1 1 d . . . H17A H 0.3200 0.1489 -0.1430 0.102 Uiso 1 1 calc R . . H17B H 0.4051 0.0270 -0.1573 0.102 Uiso 1 1 calc R . . H17C H 0.4057 0.0835 -0.0624 0.102 Uiso 1 1 calc R . . C18 C 0.37123(14) -0.2616(3) -0.07253(14) 0.0696(6) Uani 1 1 d . . . H18A H 0.4100 -0.2280 -0.0148 0.104 Uiso 1 1 calc R . . H18B H 0.4147 -0.2893 -0.1076 0.104 Uiso 1 1 calc R . . H18C H 0.3318 -0.3651 -0.0691 0.104 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 O1 0.0274(5) 0.0281(6) 0.0353(6) -0.0043(4) 0.0022(4) -0.0001(4) O2 0.0398(6) 0.0257(6) 0.0488(7) 0.0028(5) -0.0034(5) 0.0026(5) O3 0.0373(6) 0.0367(6) 0.0357(6) -0.0085(5) 0.0147(5) -0.0042(5) O4 0.0334(6) 0.0456(7) 0.0341(6) -0.0050(5) 0.0168(5) -0.0088(5) N1 0.0280(6) 0.0304(7) 0.0253(6) -0.0049(5) 0.0094(5) -0.0049(5) C1 0.0345(8) 0.0282(9) 0.0399(8) -0.0110(7) 0.0119(7) -0.0094(7) C2 0.0435(9) 0.0230(8) 0.0456(9) -0.0012(7) 0.0156(7) -0.0024(7) C3 0.0330(8) 0.0289(9) 0.0389(8) 0.0027(6) 0.0073(6) 0.0035(7) C4 0.0235(7) 0.0269(8) 0.0256(7) -0.0013(6) 0.0036(5) 0.0007(6) C5 0.0294(7) 0.0274(8) 0.0269(7) 0.0000(6) 0.0063(6) 0.0013(6) C6 0.0287(7) 0.0262(8) 0.0269(7) -0.0001(6) 0.0055(6) -0.0019(6) C7 0.0315(8) 0.0334(9) 0.0324(8) -0.0047(6) 0.0078(6) 0.0011(7) C8 0.0255(7) 0.0312(8) 0.0237(7) 0.0001(6) 0.0037(5) 0.0017(6) C9 0.0318(8) 0.0412(10) 0.0269(7) -0.0032(6) 0.0097(6) 0.0036(7) C10 0.0326(8) 0.0467(10) 0.0297(8) 0.0041(7) 0.0129(6) 0.0000(7) C11 0.0332(8) 0.0371(9) 0.0286(8) 0.0042(6) 0.0071(6) -0.0045(7) C12 0.0293(7) 0.0322(9) 0.0261(7) -0.0009(6) 0.0063(6) -0.0006(6) C13 0.0237(7) 0.0313(8) 0.0221(7) 0.0013(6) 0.0048(5) -0.0002(6) C14 0.0255(7) 0.0369(9) 0.0254(7) -0.0009(6) 0.0057(6) -0.0013(6) C15 0.0379(9) 0.0646(12) 0.0354(9) -0.0055(8) 0.0205(7) -0.0041(8) C16 0.0550(11) 0.0845(15) 0.0347(10) -0.0110(9) 0.0205(8) -0.0130(10) C17 0.0616(12) 0.0957(17) 0.0583(12) -0.0112(11) 0.0364(10) -0.0328(12) C18 0.0503(12) 0.1006(18) 0.0691(14) 0.0064(12) 0.0349(11) 0.0205(12) _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 O1 C1 1.3530(17) . ? O1 C4 1.3791(16) . ? O2 C5 1.2201(16) . ? O3 C14 1.2106(17) . ? O4 C14 1.3452(17) . ? O4 C15 1.4838(17) . ? N1 C14 1.3672(17) . ? N1 C13 1.4125(17) . ? N1 C6 1.4683(18) . ? C1 C2 1.342(2) . ? C1 H1 0.9500 . ? C2 C3 1.420(2) . ? C2 H2 0.9500 . ? C3 C4 1.3542(19) . ? C3 H3 0.9500 . ? C4 C5 1.446(2) . ? C5 C6 1.5337(19) . ? C6 C7 1.5483(18) . ? C6 H6 1.0000 . ? C7 C8 1.502(2) . ? C7 H7A 0.9900 . ? C7 H7B 0.9900 . ? C8 C9 1.3849(19) . ? C8 C13 1.3893(19) . ? C9 C10 1.383(2) . ? C9 H9 0.9500 . ? C10 C11 1.386(2) . ? C10 H10 0.9500 . ? C11 C12 1.3938(18) . ? C11 H11 0.9500 . ? C12 C13 1.3852(19) . ? C12 H12 0.9500 . ? C15 C18 1.509(3) . ? C15 C16 1.513(2) . ? C15 C17 1.520(2) . ? C16 H16A 0.9800 . ? C16 H16B 0.9800 . ? C16 H16C 0.9800 . ? C17 H17A 0.9800 . ? C17 H17B 0.9800 . ? C17 H17C 0.9800 . ? C18 H18A 0.9800 . ? C18 H18B 0.9800 . ? C18 H18C 0.9800 . ? 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 C1 O1 C4 106.35(11) . . ? C14 O4 C15 121.12(12) . . ? C14 N1 C13 125.79(12) . . ? C14 N1 C6 123.31(11) . . ? C13 N1 C6 110.91(11) . . ? C2 C1 O1 111.09(13) . . ? C2 C1 H1 124.5 . . ? O1 C1 H1 124.5 . . ? C1 C2 C3 106.40(14) . . ? C1 C2 H2 126.8 . . ? C3 C2 H2 126.8 . . ? C4 C3 C2 106.66(13) . . ? C4 C3 H3 126.7 . . ? C2 C3 H3 126.7 . . ? C3 C4 O1 109.50(12) . . ? C3 C4 C5 133.92(13) . . ? O1 C4 C5 116.56(12) . . ? O2 C5 C4 122.89(13) . . ? O2 C5 C6 121.17(13) . . ? C4 C5 C6 115.86(12) . . ? N1 C6 C5 110.21(11) . . ? N1 C6 C7 104.58(10) . . ? C5 C6 C7 110.21(11) . . ? N1 C6 H6 110.6 . . ? C5 C6 H6 110.6 . . ? C7 C6 H6 110.6 . . ? C8 C7 C6 103.91(11) . . ? C8 C7 H7A 111.0 . . ? C6 C7 H7A 111.0 . . ? C8 C7 H7B 111.0 . . ? C6 C7 H7B 111.0 . . ? H7A C7 H7B 109.0 . . ? C9 C8 C13 119.99(13) . . ? C9 C8 C7 129.40(13) . . ? C13 C8 C7 110.60(12) . . ? C10 C9 C8 119.18(14) . . ? C10 C9 H9 120.4 . . ? C8 C9 H9 120.4 . . ? C9 C10 C11 120.50(13) . . ? C9 C10 H10 119.7 . . ? C11 C10 H10 119.7 . . ? C10 C11 C12 120.97(14) . . ? C10 C11 H11 119.5 . . ? C12 C11 H11 119.5 . . ? C13 C12 C11 117.82(13) . . ? C13 C12 H12 121.1 . . ? C11 C12 H12 121.1 . . ? C12 C13 C8 121.48(13) . . ? C12 C13 N1 129.17(12) . . ? C8 C13 N1 109.34(12) . . ? O3 C14 O4 126.44(13) . . ? O3 C14 N1 124.59(13) . . ? O4 C14 N1 108.96(12) . . ? O4 C15 C18 109.52(13) . . ? O4 C15 C16 110.43(13) . . ? C18 C15 C16 113.31(16) . . ? O4 C15 C17 101.36(14) . . ? C18 C15 C17 110.88(16) . . ? C16 C15 C17 110.70(15) . . ? C15 C16 H16A 109.5 . . ? C15 C16 H16B 109.5 . . ? H16A C16 H16B 109.5 . . ? C15 C16 H16C 109.5 . . ? H16A C16 H16C 109.5 . . ? H16B C16 H16C 109.5 . . ? C15 C17 H17A 109.5 . . ? C15 C17 H17B 109.5 . . ? H17A C17 H17B 109.5 . . ? C15 C17 H17C 109.5 . . ? H17A C17 H17C 109.5 . . ? H17B C17 H17C 109.5 . . ? C15 C18 H18A 109.5 . . ? C15 C18 H18B 109.5 . . ? H18A C18 H18B 109.5 . . ? C15 C18 H18C 109.5 . . ? H18A C18 H18C 109.5 . . ? H18B C18 H18C 109.5 . . ? 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 C4 O1 C1 C2 -0.03(16) . . . . ? O1 C1 C2 C3 -0.24(17) . . . . ? C1 C2 C3 C4 0.42(17) . . . . ? C2 C3 C4 O1 -0.45(16) . . . . ? C2 C3 C4 C5 178.12(15) . . . . ? C1 O1 C4 C3 0.31(15) . . . . ? C1 O1 C4 C5 -178.54(12) . . . . ? C3 C4 C5 O2 177.61(15) . . . . ? O1 C4 C5 O2 -3.9(2) . . . . ? C3 C4 C5 C6 -5.7(2) . . . . ? O1 C4 C5 C6 172.82(11) . . . . ? C14 N1 C6 C5 -70.21(16) . . . . ? C13 N1 C6 C5 110.03(13) . . . . ? C14 N1 C6 C7 171.36(12) . . . . ? C13 N1 C6 C7 -8.40(14) . . . . ? O2 C5 C6 N1 -19.84(19) . . . . ? C4 C5 C6 N1 163.40(11) . . . . ? O2 C5 C6 C7 95.08(16) . . . . ? C4 C5 C6 C7 -81.69(15) . . . . ? N1 C6 C7 C8 6.95(13) . . . . ? C5 C6 C7 C8 -111.48(12) . . . . ? C6 C7 C8 C9 177.94(13) . . . . ? C6 C7 C8 C13 -3.50(15) . . . . ? C13 C8 C9 C10 0.8(2) . . . . ? C7 C8 C9 C10 179.28(14) . . . . ? C8 C9 C10 C11 1.3(2) . . . . ? C9 C10 C11 C12 -1.9(2) . . . . ? C10 C11 C12 C13 0.3(2) . . . . ? C11 C12 C13 C8 1.9(2) . . . . ? C11 C12 C13 N1 -177.61(12) . . . . ? C9 C8 C13 C12 -2.5(2) . . . . ? C7 C8 C13 C12 178.81(12) . . . . ? C9 C8 C13 N1 177.11(12) . . . . ? C7 C8 C13 N1 -1.61(15) . . . . ? C14 N1 C13 C12 6.3(2) . . . . ? C6 N1 C13 C12 -173.94(13) . . . . ? C14 N1 C13 C8 -173.24(12) . . . . ? C6 N1 C13 C8 6.52(15) . . . . ? C15 O4 C14 O3 -6.0(2) . . . . ? C15 O4 C14 N1 174.54(11) . . . . ? C13 N1 C14 O3 -1.5(2) . . . . ? C6 N1 C14 O3 178.79(13) . . . . ? C13 N1 C14 O4 177.98(11) . . . . ? C6 N1 C14 O4 -1.74(17) . . . . ? C14 O4 C15 C18 -60.31(18) . . . . ? C14 O4 C15 C16 65.14(18) . . . . ? C14 O4 C15 C17 -177.50(13) . . . . ? _diffrn_measured_fraction_theta_max 0.998 _diffrn_reflns_theta_full 27.88 _diffrn_measured_fraction_theta_full 0.998 _refine_diff_density_max 0.187 _refine_diff_density_min -0.223 _refine_diff_density_rms 0.045