# Supplementary Material (ESI) for Chemical Communications # This journal is (c) The Royal Society of Chemistry 2009 data_global _journal_name_full Chem.Commun. _journal_coden_Cambridge 0182 _publ_contact_author_name 'Alexander Doemling' _publ_contact_author_email ASD30@PITT.EDU _publ_section_title ; Polycyclic indole alkaloid-type compounds by MCR ; loop_ _publ_author_name 'Alexander Doemling' 'Eberhardt Herdtweck' 'Wei Wang.' # Attachment 'holn.cif' # CIF-file generated for HOLN 7016-293 # Compound P4 #=================================================================== data_HOLN-7016-293 _database_code_depnum_ccdc_archive 'CCDC 749252' #=================================================================== #=================================================================== # 5. CHEMICAL DATA #=================================================================== _chemical_name_systematic ; ; _chemical_name_common ? _chemical_formula_moiety 'C20 H21 N3 O2' _chemical_formula_structural ? _chemical_formula_analytical ? _chemical_formula_sum 'C20 H21 N3 O2' _chemical_formula_weight 335.40 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source O O 0.0492 0.0322 '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' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' #=================================================================== # 6. CRYSTAL DATA #=================================================================== _symmetry_cell_setting Monoclinic _symmetry_space_group_name_Hall '-P 2ybc' _symmetry_space_group_name_H-M 'P 21/c' _symmetry_Int_Tables_number 14 loop_ _symmetry_equiv_pos_site_id _symmetry_equiv_pos_as_xyz 1 x,y,z 2 -x,1/2+y,1/2-z 3 -x,-y,-z 4 x,1/2-y,1/2+z _cell_length_a 11.3899(5) _cell_length_b 8.9061(4) _cell_length_c 16.9450(7) _cell_angle_alpha 90 _cell_angle_beta 94.3181(18) _cell_angle_gamma 90 _cell_volume 1714.02(13) _cell_formula_units_Z 4 _cell_measurement_temperature 293(1) _cell_measurement_reflns_used 8396 _cell_measurement_theta_min 3.89 _cell_measurement_theta_max 65.99 _exptl_crystal_description fragment _exptl_crystal_colour colorless _exptl_crystal_size_max 1.02 _exptl_crystal_size_mid 0.76 _exptl_crystal_size_min 0.51 _exptl_crystal_density_meas none _exptl_crystal_density_diffrn 1.300 _exptl_crystal_density_method none _exptl_crystal_F_000 712 _exptl_absorpt_coefficient_mu 0.686 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.5365 _exptl_absorpt_correction_T_max 0.7045 _exptl_absorpt_process_details 'SADABS, Bruker, 2008b' _exptl_special_details ; Diffractometer operator E. Herdtweck scanspeed 10 s per frame dx 35 2165 films measured in 10 data sets phi-scan with delta_phi = 1.0 omega-scans with delta_omega = 1.0 ; _publ_section_exptl_prep ; The crystal was fixed in a capillary with perfluorinated ether and transferred to the diffractometer. ; _publ_section_exptl_refinement ; Solution and refinements with the program WinGX; Farrugia (1999). Hydrogen atoms could be located in the difference Fourier maps and were allowed to refine freely. ; #=================================================================== # 7. EXPERIMENTAL DATA #=================================================================== _diffrn_ambient_temperature 293(1) _diffrn_radiation_wavelength 1.54180 _diffrn_radiation_type 'Cu K\a' _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device ' \k-geometry diffractometer ' _diffrn_measurement_device_type ' Bruker \k-CCD diffractometer' _diffrn_measurement_method ' phi- and omega-rotation ' _diffrn_detector ' CCD plate ' _diffrn_detector_area_resol_mean 16 # 8 for binned mode _diffrn_standards_decay_% 0 # number of measured reflections (redundant set) _diffrn_reflns_number 11088 _diffrn_reflns_av_R_equivalents 0.0230 _diffrn_reflns_av_sigmaI/netI 0.0222 _diffrn_reflns_limit_h_min -13 _diffrn_reflns_limit_h_max 13 _diffrn_reflns_limit_k_min -10 _diffrn_reflns_limit_k_max 7 _diffrn_reflns_limit_l_min -19 _diffrn_reflns_limit_l_max 19 _diffrn_reflns_theta_min 3.89 _diffrn_reflns_theta_max 65.99 _reflns_number_total 2862 _reflns_number_gt 2665 # number of observed reflections (> n sig(I)) _reflns_threshold_expression I>2\s(I) _computing_data_collection 'APEX II Control Software (Bruker, 2008a)' _computing_cell_refinement 'SAINT (Bruker, 2008b)' _computing_data_reduction 'SAINT (Bruker, 2008b)' _computing_structure_solution 'SIR92 (Altomare, 1994)' _computing_structure_refinement 'SHELXL97 (Sheldrick, 1998)' _computing_molecular_graphics 'PLATON (Spek, 2008)' _computing_publication_material 'PLATON (Spek, 2008)' #=================================================================== # 8. REFINEMENT DATA #=================================================================== _refine_special_details ; Refinement on F^2^ for ALL reflections except for 0 with very negative F^2^ or flagged by the user for potential systematic errors. Weighted R-factors wR and all goodnesses 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 observed criterion of F^2^ > 2sigma(F^2^) is used only for calculating R_factor_obs 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 sigma _refine_ls_weighting_details 'w=1/[\s^2^(Fo^2^)+(0.0294P)^2^+0.5215P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens difmap _refine_ls_hydrogen_treatment refall _refine_ls_extinction_method SHELXL _refine_ls_extinction_coef 0.0051(3) _refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^ _refine_ls_number_reflns 2862 _refine_ls_number_parameters 311 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0353 _refine_ls_R_factor_gt 0.0329 _refine_ls_wR_factor_ref 0.0817 _refine_ls_wR_factor_gt 0.0793 _refine_ls_goodness_of_fit_ref 1.045 _refine_ls_restrained_S_all 1.045 _refine_ls_shift/su_max 0.000 _refine_ls_shift/su_mean 0.000 _diffrn_measured_fraction_theta_max 0.957 _diffrn_reflns_theta_full 65.99 _diffrn_measured_fraction_theta_full 0.957 _refine_diff_density_max 0.133 _refine_diff_density_min -0.142 _refine_diff_density_rms 0.029 #=================================================================== # 9. ATOMIC COORDINATES AND THERMAL PARAMETERS #=================================================================== loop_ _atom_site_label _atom_site_type_symbol _atom_site_thermal_displace_type _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_occupancy _atom_site_U_iso_or_equiv _atom_site_calc_flag _atom_site_refinement_flags O18 O Uani 0.34298(8) 0.89267(13) 0.13795(6) 1.000 0.0597(4) . . O22 O Uani 0.13257(9) 0.77350(12) 0.35566(6) 1.000 0.0561(3) . . N9 N Uani -0.18120(9) 0.95950(13) 0.11420(6) 1.000 0.0392(3) . . N12 N Uani 0.14307(8) 0.89328(12) 0.12736(6) 1.000 0.0371(3) . . N16 N Uani 0.14719(8) 0.98091(11) 0.27689(6) 1.000 0.0330(3) . . C1 C Uani -0.43872(13) 0.75508(19) 0.02164(9) 1.000 0.0539(5) . . C2 C Uani -0.37642(13) 0.63677(19) -0.00912(9) 1.000 0.0523(5) . . C3 C Uani -0.25562(13) 0.63027(17) 0.00094(8) 1.000 0.0458(4) . . C4 C Uani -0.19480(11) 0.74529(15) 0.04293(7) 1.000 0.0382(4) . . C5 C Uani -0.25989(11) 0.86419(15) 0.07344(7) 1.000 0.0385(4) . . C6 C Uani -0.38205(12) 0.87062(18) 0.06283(9) 1.000 0.0482(5) . . C7 C Uani -0.07296(11) 0.77445(14) 0.06559(7) 1.000 0.0375(4) . . C8 C Uani -0.06916(10) 0.90474(14) 0.10734(7) 1.000 0.0349(4) . . C10 C Uani 0.03722(12) 0.69290(16) 0.04979(9) 1.000 0.0443(4) . . C11 C Uani 0.13866(12) 0.80346(17) 0.05418(8) 1.000 0.0450(4) . . C13 C Uani 0.03748(10) 0.97545(14) 0.14779(7) 1.000 0.0340(4) . . C14 C Uani 0.25048(10) 0.93707(15) 0.16098(7) 1.000 0.0373(4) . . C15 C Uani 0.24276(10) 1.04153(14) 0.23277(7) 1.000 0.0340(4) . . C17 C Uani 0.02976(11) 0.97022(16) 0.23808(7) 1.000 0.0381(4) . . C19 C Uani 0.34467(11) 1.02987(15) 0.29587(8) 1.000 0.0398(4) . . C20 C Uani 0.32642(12) 0.87559(17) 0.33007(9) 1.000 0.0460(4) . . C21 C Uani 0.19251(11) 0.86776(14) 0.32455(7) 1.000 0.0395(4) . . C23 C Uani 0.25069(13) 1.20662(16) 0.20892(10) 1.000 0.0464(5) . . C24 C Uani 0.38564(15) 1.2307(2) 0.21078(13) 1.000 0.0664(6) . . C25 C Uani 0.44786(13) 1.10257(19) 0.25883(10) 1.000 0.0520(5) . . H9 H Uiso -0.1946(13) 1.054(2) 0.1273(9) 1.000 0.052(4) . . H11 H Uiso -0.5255(16) 0.7597(19) 0.0155(10) 1.000 0.062(5) . . H21 H Uiso -0.4185(14) 0.5559(19) -0.0387(10) 1.000 0.058(4) . . H31 H Uiso -0.2119(13) 0.5490(18) -0.0216(9) 1.000 0.051(4) . . H61 H Uiso -0.4238(15) 0.954(2) 0.0838(10) 1.000 0.062(5) . . H101 H Uiso 0.0313(13) 0.6496(18) -0.0030(10) 1.000 0.052(4) . . H102 H Uiso 0.0541(14) 0.6095(19) 0.0894(10) 1.000 0.057(4) . . H111 H Uiso 0.2157(15) 0.7531(19) 0.0537(9) 1.000 0.056(4) . . H112 H Uiso 0.1303(13) 0.8747(18) 0.0081(9) 1.000 0.051(4) . . H131 H Uiso 0.0425(11) 1.0802(17) 0.1312(8) 1.000 0.037(3) . . H171 H Uiso -0.0203(12) 1.0534(17) 0.2538(9) 1.000 0.044(4) . . H172 H Uiso -0.0043(13) 0.8727(17) 0.2528(9) 1.000 0.045(4) . . H191 H Uiso 0.3240(12) 1.1014(16) 0.3374(8) 1.000 0.039(3) . . H201 H Uiso 0.3585(14) 0.8603(19) 0.3843(10) 1.000 0.061(5) . . H202 H Uiso 0.3547(14) 0.7927(19) 0.2955(10) 1.000 0.057(4) . . H231 H Uiso 0.2164(15) 1.270(2) 0.2500(11) 1.000 0.063(5) . . H232 H Uiso 0.2113(14) 1.2318(19) 0.1555(10) 1.000 0.059(4) . . H241 H Uiso 0.4099(18) 1.230(2) 0.1553(13) 1.000 0.086(6) . . H242 H Uiso 0.409(2) 1.326(3) 0.2333(14) 1.000 0.109(8) . . H251 H Uiso 0.4875(14) 1.0331(19) 0.2232(10) 1.000 0.055(4) . . H252 H Uiso 0.5084(15) 1.1449(19) 0.2992(10) 1.000 0.063(5) . . 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 O18 0.0336(5) 0.0848(8) 0.0617(6) -0.0222(6) 0.0102(4) 0.0034(5) O22 0.0577(6) 0.0517(6) 0.0589(6) 0.0190(5) 0.0050(5) -0.0102(5) N9 0.0348(6) 0.0362(6) 0.0461(6) -0.0036(5) -0.0009(4) 0.0033(5) N12 0.0317(5) 0.0428(6) 0.0371(6) -0.0076(4) 0.0044(4) 0.0015(4) N16 0.0305(5) 0.0339(5) 0.0346(5) 0.0002(4) 0.0035(4) -0.0024(4) C1 0.0386(8) 0.0689(10) 0.0526(9) 0.0026(7) -0.0068(6) -0.0074(7) C2 0.0492(8) 0.0602(9) 0.0462(8) -0.0034(7) -0.0055(6) -0.0157(7) C3 0.0485(8) 0.0470(8) 0.0414(7) -0.0056(6) 0.0009(6) -0.0068(6) C4 0.0383(7) 0.0406(7) 0.0354(6) 0.0007(5) 0.0010(5) -0.0029(5) C5 0.0363(7) 0.0418(7) 0.0367(6) 0.0025(5) -0.0019(5) -0.0012(5) C6 0.0382(7) 0.0550(9) 0.0506(8) 0.0015(7) -0.0017(6) 0.0036(6) C7 0.0363(6) 0.0373(7) 0.0388(7) -0.0024(5) 0.0014(5) -0.0006(5) C8 0.0322(6) 0.0355(7) 0.0368(6) 0.0003(5) 0.0007(5) 0.0014(5) C10 0.0424(7) 0.0435(8) 0.0471(8) -0.0117(6) 0.0044(6) 0.0022(6) C11 0.0403(7) 0.0543(9) 0.0411(7) -0.0122(6) 0.0086(6) -0.0006(6) C13 0.0318(6) 0.0318(7) 0.0385(7) -0.0012(5) 0.0031(5) 0.0019(5) C14 0.0317(6) 0.0422(7) 0.0383(6) 0.0012(5) 0.0056(5) 0.0000(5) C15 0.0301(6) 0.0345(7) 0.0377(6) 0.0016(5) 0.0040(5) -0.0013(5) C17 0.0301(6) 0.0449(8) 0.0395(7) -0.0038(6) 0.0038(5) 0.0004(6) C19 0.0337(6) 0.0428(7) 0.0423(7) -0.0007(6) -0.0016(5) -0.0025(5) C20 0.0422(7) 0.0474(8) 0.0472(8) 0.0076(6) -0.0048(6) 0.0029(6) C21 0.0458(7) 0.0362(7) 0.0364(6) 0.0024(5) 0.0026(5) -0.0025(5) C23 0.0461(8) 0.0373(8) 0.0555(9) 0.0072(6) 0.0020(7) -0.0053(6) C24 0.0508(9) 0.0604(11) 0.0875(13) 0.0193(9) 0.0028(9) -0.0184(8) C25 0.0361(7) 0.0612(9) 0.0581(9) 0.0002(7) 0.0005(6) -0.0105(7) #================================================================== # 10. MOLECULAR GEOMETRY #=================================================================== loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_1 _geom_bond_site_symmetry_2 _geom_bond_publ_flag O18 C14 1.2168(15) . . yes O22 C21 1.2259(16) . . yes N9 C5 1.3812(17) . . yes N9 C8 1.3792(16) . . yes N12 C11 1.4733(17) . . yes N12 C13 1.4712(15) . . yes N12 C14 1.3669(15) . . yes N16 C15 1.4690(15) . . yes N16 C17 1.4485(16) . . yes N16 C21 1.3680(16) . . yes N9 H9 0.887(18) . . no C1 C2 1.393(2) . . no C1 C6 1.377(2) . . no C2 C3 1.375(2) . . no C3 C4 1.401(2) . . no C4 C5 1.4128(18) . . no C4 C7 1.4354(18) . . no C5 C6 1.3907(19) . . no C7 C10 1.4915(19) . . no C7 C8 1.3580(17) . . no C8 C13 1.4887(17) . . no C10 C11 1.516(2) . . no C13 C17 1.5398(17) . . no C14 C15 1.5392(17) . . no C15 C23 1.5293(19) . . no C15 C19 1.5213(17) . . no C19 C20 1.512(2) . . no C19 C25 1.518(2) . . no C20 C21 1.5226(19) . . no C23 C24 1.550(2) . . no C24 C25 1.543(3) . . no C1 H11 0.987(18) . . no C2 H21 0.982(17) . . no C3 H31 0.973(16) . . no C6 H61 0.964(18) . . no C10 H101 0.972(17) . . no C10 H102 1.010(17) . . no C11 H111 0.986(17) . . no C11 H112 1.005(16) . . no C13 H131 0.977(15) . . no C17 H171 0.984(15) . . no C17 H172 0.991(15) . . no C19 H191 0.991(14) . . no C20 H201 0.973(17) . . no C20 H202 1.010(17) . . no C23 H231 0.998(18) . . no C23 H232 1.005(17) . . no C24 H241 1.00(2) . . no C24 H242 0.96(3) . . no C25 H251 0.996(17) . . no C25 H252 1.007(17) . . no 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_2 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C5 N9 C8 108.07(10) . . . yes C11 N12 C13 119.44(10) . . . yes C11 N12 C14 118.58(10) . . . yes C13 N12 C14 118.81(10) . . . yes C15 N16 C17 119.17(10) . . . yes C15 N16 C21 108.06(9) . . . yes C17 N16 C21 120.94(10) . . . yes C5 N9 H9 126.2(10) . . . no C8 N9 H9 122.3(10) . . . no C2 C1 C6 121.50(14) . . . no C1 C2 C3 121.24(15) . . . no C2 C3 C4 118.97(14) . . . no C5 C4 C7 106.85(11) . . . no C3 C4 C5 118.75(12) . . . no C3 C4 C7 134.39(12) . . . no N9 C5 C4 107.76(11) . . . yes N9 C5 C6 130.14(12) . . . yes C4 C5 C6 122.08(12) . . . no C1 C6 C5 117.46(14) . . . no C8 C7 C10 121.02(11) . . . no C4 C7 C10 132.33(12) . . . no C4 C7 C8 106.63(11) . . . no N9 C8 C13 122.66(11) . . . yes C7 C8 C13 126.46(11) . . . no N9 C8 C7 110.65(11) . . . yes C7 C10 C11 108.87(11) . . . no N12 C11 C10 111.82(11) . . . yes N12 C13 C8 109.53(10) . . . yes C8 C13 C17 109.82(10) . . . no N12 C13 C17 109.12(10) . . . yes O18 C14 C15 123.52(11) . . . yes O18 C14 N12 122.89(12) . . . yes N12 C14 C15 113.53(10) . . . yes N16 C15 C19 99.94(9) . . . yes N16 C15 C14 105.59(9) . . . yes C14 C15 C23 111.36(11) . . . no C19 C15 C23 101.20(10) . . . no N16 C15 C23 123.27(11) . . . yes C14 C15 C19 115.36(10) . . . no N16 C17 C13 109.23(10) . . . yes C20 C19 C25 132.77(12) . . . no C15 C19 C20 102.23(10) . . . no C15 C19 C25 104.70(11) . . . no C19 C20 C21 100.61(11) . . . no O22 C21 C20 126.34(12) . . . yes N16 C21 C20 109.53(11) . . . yes O22 C21 N16 124.10(12) . . . yes C15 C23 C24 101.88(12) . . . no C23 C24 C25 108.89(14) . . . no C19 C25 C24 101.21(12) . . . no C2 C1 H11 121.8(10) . . . no C6 C1 H11 116.7(10) . . . no C1 C2 H21 120.2(10) . . . no C3 C2 H21 118.6(10) . . . no C2 C3 H31 121.3(9) . . . no C4 C3 H31 119.7(9) . . . no C1 C6 H61 122.5(10) . . . no C5 C6 H61 120.0(10) . . . no C7 C10 H101 110.9(9) . . . no C7 C10 H102 111.1(9) . . . no C11 C10 H101 107.6(9) . . . no C11 C10 H102 109.8(9) . . . no H101 C10 H102 108.5(14) . . . no N12 C11 H111 106.3(9) . . . no N12 C11 H112 107.8(9) . . . no C10 C11 H111 112.3(10) . . . no C10 C11 H112 110.2(9) . . . no H111 C11 H112 108.2(13) . . . no N12 C13 H131 109.9(8) . . . no C8 C13 H131 109.6(8) . . . no C17 C13 H131 108.9(8) . . . no N16 C17 H171 111.2(9) . . . no N16 C17 H172 108.0(9) . . . no C13 C17 H171 108.9(9) . . . no C13 C17 H172 109.2(9) . . . no H171 C17 H172 110.3(12) . . . no C15 C19 H191 104.2(8) . . . no C20 C19 H191 105.4(8) . . . no C25 C19 H191 104.6(8) . . . no C19 C20 H201 115.9(10) . . . no C19 C20 H202 112.5(10) . . . no C21 C20 H201 110.8(9) . . . no C21 C20 H202 107.0(9) . . . no H201 C20 H202 109.4(14) . . . no C15 C23 H231 109.0(10) . . . no C15 C23 H232 114.9(10) . . . no C24 C23 H231 110.3(10) . . . no C24 C23 H232 111.2(9) . . . no H231 C23 H232 109.3(14) . . . no C23 C24 H241 108.9(12) . . . no C23 C24 H242 112.0(14) . . . no C25 C24 H241 110.1(11) . . . no C25 C24 H242 110.0(14) . . . no H241 C24 H242 106.9(18) . . . no C19 C25 H251 112.7(10) . . . no C19 C25 H252 113.0(10) . . . no C24 C25 H251 110.5(10) . . . no C24 C25 H252 110.2(10) . . . no H251 C25 H252 109.0(13) . . . no # End of Crystallographic Information File