data_global _journal_coden_Cambridge 177 loop_ _publ_author_name 'Frank King' 'Abil Aliev' 'S Caddick' 'R Copley' _publ_contact_author_name 'Frank King' _publ_contact_author_email FD.KING@BTINTERNET.COM _publ_section_title ; An investigation into the electrophilic cyclisation of N-acyl -pyrrolidinium ions: a facile synthesis of pyrrolo-tetrahydroisoquinolones and pyrrolo-benzazepinones ; # Attachment '9.cif' data_x4486b1 _database_code_depnum_ccdc_archive 'CCDC 727741' _audit_creation_method SHELXL-97 _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C24 H26 N2 O2' _chemical_formula_sum 'C24 H26 N2 O2' _chemical_formula_weight 374.47 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' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y+1/2, -z' _cell_length_a 5.12520(10) _cell_length_b 19.6810(2) _cell_length_c 9.80400(10) _cell_angle_alpha 90.00 _cell_angle_beta 96.1731(6) _cell_angle_gamma 90.00 _cell_volume 983.19(2) _cell_formula_units_Z 2 _cell_measurement_temperature 150(2) _cell_measurement_reflns_used 1778 _cell_measurement_theta_max 72.84 _cell_measurement_theta_min 4.49 _exptl_crystal_size_max 0.24 _exptl_crystal_size_mid 0.12 _exptl_crystal_size_min 0.06 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.265 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 400 _exptl_absorpt_coefficient_mu 0.636 _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 150(2) _diffrn_radiation_wavelength 1.54178 _diffrn_radiation_type CuK\a _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 9563 _diffrn_reflns_av_R_equivalents 0.0122 _diffrn_reflns_av_sigmaI/netI 0.0146 _diffrn_reflns_limit_h_min -5 _diffrn_reflns_limit_h_max 5 _diffrn_reflns_limit_k_min -24 _diffrn_reflns_limit_k_max 23 _diffrn_reflns_limit_l_min -11 _diffrn_reflns_limit_l_max 12 _diffrn_reflns_theta_min 4.49 _diffrn_reflns_theta_max 73.28 _reflns_number_total 3747 _reflns_number_gt 3692 _reflns_threshold_expression >2sigma(I) _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^)+(0.0554P)^2^+0.1087P] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881' _refine_ls_abs_structure_Flack -0.05(17) _refine_ls_number_reflns 3747 _refine_ls_number_parameters 254 _refine_ls_number_restraints 1 _refine_ls_R_factor_all 0.0309 _refine_ls_R_factor_gt 0.0304 _refine_ls_wR_factor_ref 0.0818 _refine_ls_wR_factor_gt 0.0813 _refine_ls_goodness_of_fit_ref 1.060 _refine_ls_restrained_S_all 1.060 _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 N1 N 0.4835(2) 0.42895(6) 0.37514(10) 0.0245(2) Uani 1 1 d . . . C2 C 0.3230(3) 0.48278(7) 0.30337(13) 0.0292(3) Uani 1 1 d . . . H2A H 0.2089 0.4639 0.2245 0.035 Uiso 1 1 calc R . . H2B H 0.4356 0.5186 0.2698 0.035 Uiso 1 1 calc R . . C3 C 0.1580(3) 0.51117(7) 0.41237(13) 0.0253(3) Uani 1 1 d . . . H3A H 0.1851 0.5607 0.4242 0.030 Uiso 1 1 calc R . . H3B H -0.0311 0.5022 0.3871 0.030 Uiso 1 1 calc R . . C4 C 0.2588(2) 0.47314(6) 0.54131(13) 0.0222(2) Uani 1 1 d . . . C5 C 0.4359(3) 0.42735(6) 0.51465(12) 0.0228(3) Uani 1 1 d . . . H5A H 0.5204 0.3972 0.5810 0.027 Uiso 1 1 calc R . . C6 C 0.6541(3) 0.39167(7) 0.30965(13) 0.0245(3) Uani 1 1 d . . . O7 O 0.6814(2) 0.40284(5) 0.18891(10) 0.0341(2) Uani 1 1 d . . . C8 C 0.8031(3) 0.33563(7) 0.39100(13) 0.0256(3) Uani 1 1 d . . . H8A H 0.8756 0.3539 0.4813 0.031 Uiso 1 1 calc R . . H8B H 0.9523 0.3210 0.3418 0.031 Uiso 1 1 calc R . . C9 C 0.6325(3) 0.27430(6) 0.41320(13) 0.0240(3) Uani 1 1 d . . . C10 C 0.4393(3) 0.25253(7) 0.31179(14) 0.0283(3) Uani 1 1 d . . . H10A H 0.4123 0.2765 0.2274 0.034 Uiso 1 1 calc R . . C11 C 0.2862(3) 0.19627(8) 0.33265(17) 0.0345(3) Uani 1 1 d . . . H11A H 0.1537 0.1823 0.2631 0.041 Uiso 1 1 calc R . . C12 C 0.3256(3) 0.16017(7) 0.45500(17) 0.0349(3) Uani 1 1 d . . . H12A H 0.2211 0.1215 0.4694 0.042 Uiso 1 1 calc R . . C13 C 0.5186(3) 0.18118(7) 0.55555(15) 0.0329(3) Uani 1 1 d . . . H13A H 0.5477 0.1565 0.6391 0.040 Uiso 1 1 calc R . . C14 C 0.6706(3) 0.23815(7) 0.53549(15) 0.0295(3) Uani 1 1 d . . . H14A H 0.8011 0.2524 0.6058 0.035 Uiso 1 1 calc R . . C15 C 0.1510(2) 0.48733(6) 0.67513(13) 0.0227(2) Uani 1 1 d . . . H15A H -0.0451 0.4855 0.6614 0.027 Uiso 1 1 calc R . . N16 N 0.2484(2) 0.43972(6) 0.78384(10) 0.0236(2) Uani 1 1 d . . . C17 C 0.4603(3) 0.46922(7) 0.87958(14) 0.0307(3) Uani 1 1 d . . . H17A H 0.6216 0.4413 0.8832 0.037 Uiso 1 1 calc R . . H17B H 0.4061 0.4731 0.9732 0.037 Uiso 1 1 calc R . . C18 C 0.5033(3) 0.53929(7) 0.81886(14) 0.0281(3) Uani 1 1 d . . . H18A H 0.6447 0.5379 0.7576 0.034 Uiso 1 1 calc R . . H18B H 0.5498 0.5731 0.8922 0.034 Uiso 1 1 calc R . . C19 C 0.2396(3) 0.55641(7) 0.73837(14) 0.0268(3) Uani 1 1 d . . . H19A H 0.2602 0.5906 0.6663 0.032 Uiso 1 1 calc R . . H19B H 0.1131 0.5736 0.7997 0.032 Uiso 1 1 calc R . . C20 C 0.1184(3) 0.38185(7) 0.80454(13) 0.0250(3) Uani 1 1 d . . . O21 O -0.0754(2) 0.36409(5) 0.72847(10) 0.0327(2) Uani 1 1 d . . . C22 C 0.2249(4) 0.34034(8) 0.92952(15) 0.0385(4) Uani 1 1 d . . . H22A H 0.4172 0.3353 0.9299 0.046 Uiso 1 1 calc R . . H22B H 0.1917 0.3652 1.0138 0.046 Uiso 1 1 calc R . . C23 C 0.1019(3) 0.27109(7) 0.93135(13) 0.0294(3) Uani 1 1 d . . . C24 C 0.1856(3) 0.21973(8) 0.84999(15) 0.0365(3) Uani 1 1 d . . . H24A H 0.3207 0.2285 0.7932 0.044 Uiso 1 1 calc R . . C25 C 0.0737(4) 0.15538(8) 0.85046(16) 0.0403(4) Uani 1 1 d . . . H25A H 0.1320 0.1205 0.7939 0.048 Uiso 1 1 calc R . . C26 C -0.1222(3) 0.14207(8) 0.93313(16) 0.0382(3) Uani 1 1 d . . . H26A H -0.1976 0.0980 0.9344 0.046 Uiso 1 1 calc R . . C27 C -0.2079(3) 0.19327(9) 1.01397(15) 0.0371(3) Uani 1 1 d . . . H27A H -0.3440 0.1845 1.0701 0.044 Uiso 1 1 calc R . . C28 C -0.0962(3) 0.25734(8) 1.01348(14) 0.0322(3) Uani 1 1 d . . . H28A H -0.1556 0.2921 1.0698 0.039 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 N1 0.0288(6) 0.0244(5) 0.0200(5) 0.0008(4) 0.0019(4) 0.0015(4) C2 0.0362(7) 0.0279(7) 0.0232(6) 0.0041(5) 0.0019(5) 0.0041(5) C3 0.0281(7) 0.0215(6) 0.0254(6) 0.0013(4) -0.0005(5) 0.0005(5) C4 0.0238(6) 0.0205(6) 0.0218(6) 0.0002(4) -0.0009(4) -0.0019(4) C5 0.0261(7) 0.0226(6) 0.0194(5) 0.0005(5) 0.0009(4) -0.0013(5) C6 0.0256(7) 0.0243(6) 0.0233(6) -0.0042(5) 0.0015(4) -0.0043(5) O7 0.0449(6) 0.0361(5) 0.0224(5) -0.0024(4) 0.0088(4) 0.0018(4) C8 0.0228(7) 0.0285(6) 0.0253(6) -0.0049(5) 0.0016(4) 0.0014(5) C9 0.0242(7) 0.0228(6) 0.0253(6) -0.0051(5) 0.0035(5) 0.0050(5) C10 0.0302(7) 0.0250(6) 0.0289(6) -0.0016(5) -0.0007(5) 0.0036(5) C11 0.0299(7) 0.0301(7) 0.0414(8) -0.0044(6) -0.0058(6) 0.0001(5) C12 0.0332(8) 0.0243(7) 0.0484(8) -0.0011(6) 0.0092(6) -0.0006(5) C13 0.0446(9) 0.0252(7) 0.0299(6) 0.0010(5) 0.0084(6) 0.0069(6) C14 0.0331(8) 0.0278(7) 0.0267(6) -0.0048(5) -0.0004(5) 0.0052(5) C15 0.0211(6) 0.0234(6) 0.0235(6) -0.0010(5) 0.0016(4) 0.0010(4) N16 0.0244(6) 0.0261(6) 0.0196(5) -0.0019(4) -0.0003(4) 0.0001(4) C17 0.0275(7) 0.0340(7) 0.0291(7) -0.0020(6) -0.0044(5) -0.0041(5) C18 0.0251(7) 0.0280(7) 0.0313(6) -0.0067(5) 0.0034(5) -0.0013(5) C19 0.0271(7) 0.0244(6) 0.0291(6) -0.0061(5) 0.0039(5) 0.0014(5) C20 0.0292(7) 0.0244(6) 0.0208(6) -0.0022(5) -0.0003(5) 0.0014(5) O21 0.0371(6) 0.0287(5) 0.0296(5) 0.0024(4) -0.0096(4) -0.0058(4) C22 0.0496(9) 0.0321(7) 0.0300(7) 0.0058(6) -0.0141(6) -0.0088(6) C23 0.0360(8) 0.0282(7) 0.0215(6) 0.0035(5) -0.0076(5) -0.0003(5) C24 0.0380(9) 0.0434(9) 0.0284(7) -0.0010(6) 0.0052(6) -0.0006(6) C25 0.0537(10) 0.0342(8) 0.0321(7) -0.0070(6) 0.0013(7) 0.0059(7) C26 0.0496(10) 0.0294(7) 0.0332(7) 0.0037(6) -0.0065(6) -0.0065(6) C27 0.0398(9) 0.0418(8) 0.0298(7) 0.0073(6) 0.0042(6) -0.0022(7) C28 0.0392(8) 0.0315(7) 0.0252(6) -0.0005(6) -0.0001(5) 0.0072(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 N1 C6 1.3549(17) . yes N1 C5 1.4153(16) . yes N1 C2 1.4728(17) . yes C2 C3 1.5376(19) . yes C2 H2A 0.9900 . ? C2 H2B 0.9900 . ? C3 C4 1.5115(17) . yes C3 H3A 0.9900 . ? C3 H3B 0.9900 . ? C4 C5 1.3248(18) . yes C4 C15 1.5035(17) . yes C5 H5A 0.9500 . ? C6 O7 1.2266(17) . yes C6 C8 1.5180(19) . yes C8 C9 1.5198(19) . yes C8 H8A 0.9900 . ? C8 H8B 0.9900 . ? C9 C14 1.390(2) . yes C9 C10 1.3931(19) . yes C10 C11 1.385(2) . yes C10 H10A 0.9500 . ? C11 C12 1.390(2) . yes C11 H11A 0.9500 . ? C12 C13 1.383(2) . yes C12 H12A 0.9500 . ? C13 C14 1.391(2) . yes C13 H13A 0.9500 . ? C14 H14A 0.9500 . ? C15 N16 1.4660(16) . yes C15 C19 1.5422(18) . yes C15 H15A 1.0000 . ? N16 C20 1.3460(18) . yes N16 C17 1.4759(16) . yes C17 C18 1.527(2) . yes C17 H17A 0.9900 . ? C17 H17B 0.9900 . ? C18 C19 1.5278(19) . yes C18 H18A 0.9900 . ? C18 H18B 0.9900 . ? C19 H19A 0.9900 . ? C19 H19B 0.9900 . ? C20 O21 1.2268(16) . yes C20 C22 1.5242(18) . yes C22 C23 1.502(2) . yes C22 H22A 0.9900 . ? C22 H22B 0.9900 . ? C23 C24 1.384(2) . yes C23 C28 1.389(2) . yes C24 C25 1.390(2) . yes C24 H24A 0.9500 . ? C25 C26 1.381(3) . yes C25 H25A 0.9500 . ? C26 C27 1.383(2) . yes C26 H26A 0.9500 . ? C27 C28 1.385(2) . yes C27 H27A 0.9500 . ? C28 H28A 0.9500 . ? 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 C6 N1 C5 129.28(11) . . yes C6 N1 C2 121.24(11) . . yes C5 N1 C2 109.41(11) . . yes N1 C2 C3 104.48(10) . . yes N1 C2 H2A 110.9 . . ? C3 C2 H2A 110.9 . . ? N1 C2 H2B 110.9 . . ? C3 C2 H2B 110.9 . . ? H2A C2 H2B 108.9 . . ? C4 C3 C2 103.72(11) . . yes C4 C3 H3A 111.0 . . ? C2 C3 H3A 111.0 . . ? C4 C3 H3B 111.0 . . ? C2 C3 H3B 111.0 . . ? H3A C3 H3B 109.0 . . ? C5 C4 C15 128.49(11) . . yes C5 C4 C3 110.59(11) . . yes C15 C4 C3 120.87(11) . . yes C4 C5 N1 111.62(11) . . yes C4 C5 H5A 124.2 . . ? N1 C5 H5A 124.2 . . ? O7 C6 N1 120.45(13) . . yes O7 C6 C8 122.28(12) . . yes N1 C6 C8 117.27(11) . . yes C6 C8 C9 112.81(11) . . yes C6 C8 H8A 109.0 . . ? C9 C8 H8A 109.0 . . ? C6 C8 H8B 109.0 . . ? C9 C8 H8B 109.0 . . ? H8A C8 H8B 107.8 . . ? C14 C9 C10 118.77(13) . . yes C14 C9 C8 120.04(12) . . yes C10 C9 C8 121.18(12) . . yes C11 C10 C9 120.73(13) . . yes C11 C10 H10A 119.6 . . ? C9 C10 H10A 119.6 . . ? C10 C11 C12 120.26(14) . . yes C10 C11 H11A 119.9 . . ? C12 C11 H11A 119.9 . . ? C13 C12 C11 119.27(14) . . yes C13 C12 H12A 120.4 . . ? C11 C12 H12A 120.4 . . ? C12 C13 C14 120.58(13) . . yes C12 C13 H13A 119.7 . . ? C14 C13 H13A 119.7 . . ? C9 C14 C13 120.38(13) . . yes C9 C14 H14A 119.8 . . ? C13 C14 H14A 119.8 . . ? N16 C15 C4 112.78(10) . . yes N16 C15 C19 102.05(10) . . yes C4 C15 C19 113.25(11) . . yes N16 C15 H15A 109.5 . . ? C4 C15 H15A 109.5 . . ? C19 C15 H15A 109.5 . . ? C20 N16 C15 121.00(11) . . yes C20 N16 C17 125.41(11) . . yes C15 N16 C17 112.38(10) . . yes N16 C17 C18 103.57(11) . . yes N16 C17 H17A 111.0 . . ? C18 C17 H17A 111.0 . . ? N16 C17 H17B 111.0 . . ? C18 C17 H17B 111.0 . . ? H17A C17 H17B 109.0 . . ? C17 C18 C19 104.10(11) . . yes C17 C18 H18A 110.9 . . ? C19 C18 H18A 110.9 . . ? C17 C18 H18B 110.9 . . ? C19 C18 H18B 110.9 . . ? H18A C18 H18B 109.0 . . ? C18 C19 C15 102.66(11) . . yes C18 C19 H19A 111.2 . . ? C15 C19 H19A 111.2 . . ? C18 C19 H19B 111.2 . . ? C15 C19 H19B 111.2 . . ? H19A C19 H19B 109.1 . . ? O21 C20 N16 122.07(12) . . yes O21 C20 C22 122.19(12) . . yes N16 C20 C22 115.74(12) . . yes C23 C22 C20 112.41(12) . . yes C23 C22 H22A 109.1 . . ? C20 C22 H22A 109.1 . . ? C23 C22 H22B 109.1 . . ? C20 C22 H22B 109.1 . . ? H22A C22 H22B 107.9 . . ? C24 C23 C28 118.87(14) . . yes C24 C23 C22 119.96(15) . . yes C28 C23 C22 121.17(14) . . yes C23 C24 C25 120.67(15) . . yes C23 C24 H24A 119.7 . . ? C25 C24 H24A 119.7 . . ? C26 C25 C24 120.04(15) . . yes C26 C25 H25A 120.0 . . ? C24 C25 H25A 120.0 . . ? C25 C26 C27 119.59(15) . . yes C25 C26 H26A 120.2 . . ? C27 C26 H26A 120.2 . . ? C26 C27 C28 120.31(15) . . yes C26 C27 H27A 119.8 . . ? C28 C27 H27A 119.8 . . ? C27 C28 C23 120.51(13) . . yes C27 C28 H28A 119.7 . . ? C23 C28 H28A 119.7 . . ? 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 C6 N1 C2 C3 179.37(11) . . . . yes C5 N1 C2 C3 -3.48(14) . . . . yes N1 C2 C3 C4 4.19(13) . . . . yes C2 C3 C4 C5 -3.75(14) . . . . yes C2 C3 C4 C15 178.58(11) . . . . yes C15 C4 C5 N1 179.15(12) . . . . yes C3 C4 C5 N1 1.71(15) . . . . yes C6 N1 C5 C4 178.08(12) . . . . yes C2 N1 C5 C4 1.23(15) . . . . yes C5 N1 C6 O7 -175.38(13) . . . . yes C2 N1 C6 O7 1.15(19) . . . . yes C5 N1 C6 C8 5.69(19) . . . . yes C2 N1 C6 C8 -177.78(12) . . . . yes O7 C6 C8 C9 -104.91(15) . . . . yes N1 C6 C8 C9 73.99(14) . . . . yes C6 C8 C9 C14 -144.20(12) . . . . yes C6 C8 C9 C10 36.86(17) . . . . yes C14 C9 C10 C11 0.6(2) . . . . yes C8 C9 C10 C11 179.52(13) . . . . yes C9 C10 C11 C12 -0.8(2) . . . . yes C10 C11 C12 C13 0.2(2) . . . . yes C11 C12 C13 C14 0.6(2) . . . . yes C10 C9 C14 C13 0.20(19) . . . . yes C8 C9 C14 C13 -178.77(12) . . . . yes C12 C13 C14 C9 -0.8(2) . . . . yes C5 C4 C15 N16 -4.49(19) . . . . yes C3 C4 C15 N16 172.72(11) . . . . yes C5 C4 C15 C19 110.77(15) . . . . yes C3 C4 C15 C19 -72.02(14) . . . . yes C4 C15 N16 C20 -90.68(13) . . . . yes C19 C15 N16 C20 147.50(11) . . . . yes C4 C15 N16 C17 101.25(12) . . . . yes C19 C15 N16 C17 -20.57(13) . . . . yes C20 N16 C17 C18 -170.50(12) . . . . yes C15 N16 C17 C18 -3.06(14) . . . . yes N16 C17 C18 C19 25.85(13) . . . . yes C17 C18 C19 C15 -38.44(13) . . . . yes N16 C15 C19 C18 35.63(12) . . . . yes C4 C15 C19 C18 -85.87(12) . . . . yes C15 N16 C20 O21 5.10(19) . . . . yes C17 N16 C20 O21 171.53(13) . . . . yes C15 N16 C20 C22 -174.10(12) . . . . yes C17 N16 C20 C22 -7.66(19) . . . . yes O21 C20 C22 C23 11.3(2) . . . . yes N16 C20 C22 C23 -169.55(13) . . . . yes C20 C22 C23 C24 78.78(19) . . . . yes C20 C22 C23 C28 -101.09(16) . . . . yes C28 C23 C24 C25 -0.1(2) . . . . yes C22 C23 C24 C25 -179.97(14) . . . . yes C23 C24 C25 C26 -0.3(2) . . . . yes C24 C25 C26 C27 0.7(2) . . . . yes C25 C26 C27 C28 -0.8(2) . . . . yes C26 C27 C28 C23 0.4(2) . . . . yes C24 C23 C28 C27 0.1(2) . . . . yes C22 C23 C28 C27 179.93(13) . . . . yes 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 C5 H5A O21 0.95 2.48 3.3301(15) 148.6 1_655 C8 H8A O21 0.99 2.42 3.3474(16) 156.2 1_655 C14 H14A O21 0.95 2.55 3.2999(17) 135.7 1_655 _diffrn_measured_fraction_theta_max 0.957 _diffrn_reflns_theta_full 73.28 _diffrn_measured_fraction_theta_full 0.957 _refine_diff_density_max 0.172 _refine_diff_density_min -0.161 _refine_diff_density_rms 0.032 _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M 'P 21' _exptl_absorpt_correction_type integration _exptl_absorpt_correction_T_min 0.8922 _exptl_absorpt_correction_T_max 0.9629 loop_ _exptl_crystal_face_index_h _exptl_crystal_face_index_k _exptl_crystal_face_index_l _exptl_crystal_face_perp_dist 1.00 0.00 0.00 0.1200 -1.00 0.00 0.00 0.1200 0.00 1.00 0.00 0.0600 0.00 -1.00 0.00 0.0600 0.00 0.00 1.00 0.0300 0.00 0.00 -1.00 0.0300 _exptl_crystal_description block _exptl_crystal_colour colourless _chemical_name_systematic ; 1-(Phenylacetyl)-4-[(2S)-1-(phenylacetyl)-2-pyrrolidinyl]-2,3-dihydro-1H-pyrrole ; _computing_data_merging 'SHELXTL V6.10 UNIX (Bruker, 2001)' _computing_structure_solution 'SHELXTL V6.10 UNIX (Bruker, 2001)' _computing_structure_refinement 'SHELXTL V6.10 UNIX (Bruker, 2001)' _computing_molecular_graphics 'SHELXTL V5.10 UNIX (Bruker, 1997)' _computing_publication_material 'SHELXTL V6.10 UNIX (Bruker, 2001)' _atom_sites_solution_primary direct _atom_sites_solution_secondary ? _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment constr _chemical_absolute_configuration ad _computing_data_collection 'SMART V5.604 [NT] (Bruker, 2000)' _computing_cell_refinement 'SMART V5.604 [NT] (Bruker, 2000)' _computing_data_reduction 'SAINT+ V6.45A [NT] (Bruker, 2003)' _diffrn_measurement_device_type 'Bruker AXS SMART 6000' _diffrn_measurement_method \w _diffrn_radiation_collimation '0.8 mm double-pinhole' _diffrn_radiation_monochromator 'graphite - parallel geometry' _diffrn_radiation_source 'normal focus sealed tube'