data_trans-4a _audit_creation_method SHELXL-97 _publ_contact_author 'Renata Riva' _publ_contact_email 'riva@chimica.unige.it' loop_ _publ_author_name 'Renata Riva' 'Luca Banfi' 'Andrea Basso' 'Valentina Cerulli' 'Giuseppe Guanti' 'Marcella Pani' _journal_name_full 'Organic letters' _chemical_name_systematic ; 6-(N-benzyl-Npropanoyl)amino-13-methylene-5-oxo-2,3,5,6,12,13-hexahydro-1H-benzo[d]pyrrolo[1,2-a]azepine ; _chemical_formula_sum 'C24 H26 N2 O2' _chemical_formula_moiety 'C24 H26 N2 O2' _chemical_formula_weight 374.47 _chemical_temperature_decomposition_gt '433.1' _chemical_temperature_decomposition_lt '435.9' _exptl_crystal_colour 'white' _exptl_crystal_description 'irregular prism' _exptl_crystal_size_max 0.40 _exptl_crystal_size_mid 0.40 _exptl_crystal_size_min 0.25 _exptl_crystal_preparation 'crystallized from dichloromethane/isopropylether' 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 'P 21/n' _symmetry_space_group_name_Hall '-P 2yn' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, y+1/2, -z+1/2' '-x, -y, -z' 'x-1/2, -y-1/2, z-1/2' _cell_length_a 9.641(1) _cell_length_b 16.342(3) _cell_length_c 12.793(1) _cell_angle_alpha 90.00 _cell_angle_beta 93.38(1) _cell_angle_gamma 90.00 _cell_volume 2012.1(5) _cell_formula_units_Z 4 _cell_measurement_temperature 295(2) _cell_measurement_reflns_used 25 _cell_measurement_theta_min 15.13 _cell_measurement_theta_max 17.31 _exptl_crystal_density_diffrn 1.236 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 800 _exptl_absorpt_coefficient_mu 0.079 _exptl_absorpt_correction_type psi-scan _exptl_absorpt_correction_T_min 0.8741 _exptl_absorpt_correction_T_max 0.9980 _exptl_absorpt_process_details '(North, Phillips & Mathews)' _diffrn_ambient_temperature 295(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_standards_number 2 _diffrn_standards_interval_time 180 _diffrn_standards_decay_% 0 _diffrn_reflns_number 5015 _diffrn_reflns_av_R_equivalents 0.0297 _diffrn_reflns_av_sigmaI/netI 0.0803 _diffrn_reflns_limit_h_min 0 _diffrn_reflns_limit_h_max 12 _diffrn_reflns_limit_k_min 0 _diffrn_reflns_limit_k_max 21 _diffrn_reflns_limit_l_min -16 _diffrn_reflns_limit_l_max 16 _diffrn_reflns_theta_min 2.02 _diffrn_reflns_theta_max 28.38 _reflns_number_total 4813 _reflns_number_gt 2072 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'MACH3 software' _computing_cell_refinement 'MACH3 software' _computing_data_reduction 'local software' _computing_structure_solution 'sir2004 (J. Appl. Cryst. 38, 2005, 381-388)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_publication_material 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'ORTEP-III for windows' _refine_special_details ; All non-hydrogen atoms were anisotropically refined. While most of the hydrogen atoms could be isotropically refined without constraints, for the H atoms bonded to C1, C2, C18, C19 and C24 an idealized geometry was necessary. An additional restraint was applied to the displacement parameters of the hydrogens bonded to C2 and C19, for which a same refinable value was imposed. ; _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^)+(0.0548P)^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 mixed _refine_ls_extinction_method SHELXL _refine_ls_extinction_coef 0.0096(11) _refine_ls_extinction_expression 'Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^' _refine_ls_number_reflns 4813 _refine_ls_number_parameters 326 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.1685 _refine_ls_R_factor_gt 0.0623 _refine_ls_wR_factor_ref 0.1341 _refine_ls_wR_factor_gt 0.1109 _refine_ls_goodness_of_fit_ref 0.914 _refine_ls_restrained_S_all 0.914 _refine_ls_shift/su_max 0.002 _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 0.3178(3) 0.43004(19) -0.1982(2) 0.0846(9) Uani 1 1 d . . . H1A H 0.4107 0.4189 -0.2197 0.107(11) Uiso 1 1 calc R . . H1B H 0.3164 0.4841 -0.1670 0.113(11) Uiso 1 1 calc R . . C2 C 0.2127(3) 0.4242(2) -0.2905(2) 0.1055(11) Uani 1 1 d . . . H2A H 0.1308 0.4565 -0.2782 0.154(10) Uiso 1 1 calc R . . H2B H 0.2524 0.4439 -0.3538 0.154(10) Uiso 1 1 calc R . . C3 C 0.1766(4) 0.3358(2) -0.3004(2) 0.0828(9) Uani 1 1 d . . . N4 N 0.20796(19) 0.30420(12) -0.19344(13) 0.0596(5) Uani 1 1 d . . . C5 C 0.1668(2) 0.22815(17) -0.16994(17) 0.0621(7) Uani 1 1 d . . . C6 C 0.2200(2) 0.19247(15) -0.06361(17) 0.0548(6) Uani 1 1 d . . . C7 C 0.3764(2) 0.18599(13) -0.06397(15) 0.0501(6) Uani 1 1 d . . . C8 C 0.4399(3) 0.10993(17) -0.07194(19) 0.0672(7) Uani 1 1 d . . . C9 C 0.5808(3) 0.1034(2) -0.08264(19) 0.0740(8) Uani 1 1 d . . . C10 C 0.6612(3) 0.17219(19) -0.08465(19) 0.0685(7) Uani 1 1 d . . . C11 C 0.6007(2) 0.24800(17) -0.07453(16) 0.0560(6) Uani 1 1 d . . . C12 C 0.4591(2) 0.25666(13) -0.06372(14) 0.0452(5) Uani 1 1 d . . . C13 C 0.3971(2) 0.33783(13) -0.04885(16) 0.0482(5) Uani 1 1 d . . . C14 C 0.2738(2) 0.36609(14) -0.12170(18) 0.0551(6) Uani 1 1 d . . . O15 O 0.1067(2) 0.18334(12) -0.23591(13) 0.0922(6) Uani 1 1 d . . . N16 N 0.17796(18) 0.23560(11) 0.03012(13) 0.0508(5) Uani 1 1 d . . . C17 C 0.0517(2) 0.27320(16) 0.02573(18) 0.0617(7) Uani 1 1 d . . . C18 C 0.0096(3) 0.31489(19) 0.1242(2) 0.0791(8) Uani 1 1 d . . . H18A H -0.0164 0.2736 0.1739 0.127(12) Uiso 1 1 calc R . . H18B H 0.0887 0.3446 0.1554 0.105(10) Uiso 1 1 calc R . . C19 C -0.1087(3) 0.3728(2) 0.1046(3) 0.1165(12) Uani 1 1 d . . . H19A H -0.1869 0.3439 0.0728 0.145(8) Uiso 1 1 calc R . . H19B H -0.0817 0.4156 0.0587 0.145(8) Uiso 1 1 calc R . . H19C H -0.1336 0.3960 0.1698 0.145(8) Uiso 1 1 calc R . . O20 O -0.02449(17) 0.27525(12) -0.05601(13) 0.0834(6) Uani 1 1 d . . . C21 C 0.2528(3) 0.21262(16) 0.13050(18) 0.0541(6) Uani 1 1 d . . . C22 C 0.2190(2) 0.12873(13) 0.16965(16) 0.0494(5) Uani 1 1 d . . . C23 C 0.1126(3) 0.08027(16) 0.12316(19) 0.0612(7) Uani 1 1 d . . . C24 C 0.0875(3) 0.00282(17) 0.1619(2) 0.0749(8) Uani 1 1 d . . . H24 H 0.0177 -0.0294 0.1301 0.099(10) Uiso 1 1 calc R . . C25 C 0.1651(4) -0.0265(2) 0.2469(3) 0.0869(10) Uani 1 1 d . . . C26 C 0.2687(4) 0.0210(2) 0.2961(2) 0.0883(10) Uani 1 1 d . . . C27 C 0.2968(3) 0.09819(18) 0.25755(19) 0.0672(7) Uani 1 1 d . . . C28 C 0.4531(3) 0.38782(18) 0.0253(2) 0.0681(7) Uani 1 1 d . . . H3A H 0.085(3) 0.3227(15) -0.325(2) 0.092(9) Uiso 1 1 d . . . H3B H 0.238(4) 0.3026(18) -0.351(3) 0.132(12) Uiso 1 1 d . . . H6 H 0.1858(19) 0.1381(12) -0.0651(15) 0.054(6) Uiso 1 1 d . . . H8 H 0.380(3) 0.0657(16) -0.0709(19) 0.084(9) Uiso 1 1 d . . . H9 H 0.623(2) 0.0483(16) -0.0862(18) 0.093(9) Uiso 1 1 d . . . H10 H 0.765(3) 0.1686(14) -0.0916(19) 0.091(9) Uiso 1 1 d . . . H11 H 0.656(2) 0.2954(12) -0.0774(15) 0.048(6) Uiso 1 1 d . . . H14 H 0.200(2) 0.3872(14) -0.0820(18) 0.077(8) Uiso 1 1 d . . . H21A H 0.238(2) 0.2538(13) 0.1831(17) 0.060(7) Uiso 1 1 d . . . H21B H 0.351(2) 0.2164(12) 0.1232(16) 0.064(7) Uiso 1 1 d . . . H23 H 0.0534(19) 0.1010(12) 0.0610(16) 0.053(6) Uiso 1 1 d . . . H25 H 0.153(3) -0.0828(19) 0.279(2) 0.113(10) Uiso 1 1 d . . . H26 H 0.325(3) 0.0060(16) 0.361(2) 0.107(10) Uiso 1 1 d . . . H27 H 0.366(2) 0.1332(15) 0.2901(18) 0.076(8) Uiso 1 1 d . . . H28A H 0.538(3) 0.3684(15) 0.077(2) 0.095(9) Uiso 1 1 d . . . H28B H 0.410(2) 0.4401(15) 0.0342(18) 0.078(8) 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 0.089(2) 0.081(2) 0.083(2) 0.0326(17) 0.0034(17) -0.0057(16) C2 0.105(2) 0.119(3) 0.091(2) 0.049(2) -0.008(2) 0.002(2) C3 0.073(2) 0.129(3) 0.0457(16) 0.0237(17) -0.0026(15) 0.003(2) N4 0.0586(12) 0.0841(15) 0.0355(10) 0.0077(10) -0.0027(9) -0.0114(11) C5 0.0583(15) 0.0858(19) 0.0417(13) -0.0033(13) -0.0020(11) -0.0216(14) C6 0.0635(16) 0.0566(15) 0.0442(13) -0.0043(11) 0.0020(11) -0.0270(12) C7 0.0603(15) 0.0535(15) 0.0367(12) -0.0044(10) 0.0044(10) -0.0107(12) C8 0.091(2) 0.0546(18) 0.0570(16) -0.0074(13) 0.0102(14) -0.0089(17) C9 0.097(2) 0.069(2) 0.0578(16) -0.0054(14) 0.0144(15) 0.0182(19) C10 0.0669(19) 0.085(2) 0.0547(16) -0.0076(14) 0.0103(13) 0.0122(17) C11 0.0551(15) 0.0687(18) 0.0443(13) -0.0025(12) 0.0047(11) -0.0106(14) C12 0.0530(13) 0.0509(14) 0.0315(11) -0.0013(10) 0.0022(9) -0.0082(11) C13 0.0546(13) 0.0490(13) 0.0415(12) 0.0011(11) 0.0086(10) -0.0092(11) C14 0.0534(14) 0.0593(15) 0.0533(14) 0.0039(12) 0.0089(12) -0.0038(12) O15 0.1016(14) 0.1215(16) 0.0516(10) -0.0167(11) -0.0120(10) -0.0442(12) N16 0.0496(11) 0.0637(12) 0.0391(10) 0.0036(9) 0.0023(8) -0.0128(9) C17 0.0532(15) 0.0809(18) 0.0509(14) 0.0122(13) 0.0015(12) -0.0153(13) C18 0.0689(19) 0.104(2) 0.0654(17) -0.0037(17) 0.0094(15) 0.0017(17) C19 0.097(2) 0.148(3) 0.104(3) -0.027(2) -0.0006(19) 0.028(2) O20 0.0554(10) 0.1386(17) 0.0552(11) 0.0096(11) -0.0043(8) -0.0032(10) C21 0.0517(16) 0.0688(17) 0.0412(13) 0.0029(12) -0.0026(11) -0.0109(13) C22 0.0519(13) 0.0581(14) 0.0395(12) -0.0010(11) 0.0137(10) 0.0004(12) C23 0.0639(16) 0.0692(17) 0.0516(15) 0.0031(13) 0.0133(13) -0.0137(14) C24 0.085(2) 0.0659(18) 0.0769(19) -0.0075(16) 0.0344(17) -0.0126(16) C25 0.120(3) 0.063(2) 0.083(2) 0.0091(18) 0.045(2) 0.013(2) C26 0.115(3) 0.085(2) 0.0659(19) 0.0166(18) 0.0150(19) 0.031(2) C27 0.0744(19) 0.074(2) 0.0538(16) 0.0028(15) 0.0068(14) 0.0087(16) C28 0.084(2) 0.0569(18) 0.0629(16) -0.0110(14) 0.0015(15) -0.0088(16) 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 C14 1.509(3) . ? C1 C2 1.513(4) . ? C1 H1A 0.9700 . ? C1 H1B 0.9700 . ? C2 C3 1.489(4) . ? C2 H2A 0.9700 . ? C2 H2B 0.9700 . ? C3 N4 1.478(3) . ? C3 H3A 0.94(3) . ? C3 H3B 1.05(3) . ? N4 C5 1.344(3) . ? N4 C14 1.483(3) . ? C5 O15 1.236(3) . ? C5 C6 1.540(3) . ? C6 N16 1.468(3) . ? C6 C7 1.512(3) . ? C6 H6 0.948(19) . ? C7 C8 1.392(3) . ? C7 C12 1.403(3) . ? C8 C9 1.377(4) . ? C8 H8 0.93(2) . ? C9 C10 1.366(4) . ? C9 H9 0.99(3) . ? C10 C11 1.378(3) . ? C10 H10 1.01(3) . ? C11 C12 1.388(3) . ? C11 H11 0.943(19) . ? C12 C13 1.472(3) . ? C13 C28 1.341(3) . ? C13 C14 1.538(3) . ? C14 H14 0.96(2) . ? N16 C17 1.362(3) . ? N16 C21 1.484(3) . ? C17 O20 1.242(2) . ? C17 C18 1.509(3) . ? C18 C19 1.491(4) . ? C18 H18A 0.9700 . ? C18 H18B 0.9700 . ? C19 H19A 0.9600 . ? C19 H19B 0.9600 . ? C19 H19C 0.9600 . ? C21 C22 1.502(3) . ? C21 H21A 0.97(2) . ? C21 H21B 0.96(2) . ? C22 C23 1.400(3) . ? C22 C27 1.406(3) . ? C23 C24 1.386(3) . ? C23 H23 1.009(19) . ? C24 C25 1.369(4) . ? C24 H24 0.9300 . ? C25 C26 1.387(4) . ? C25 H25 1.01(3) . ? C26 C27 1.387(4) . ? C26 H26 1.00(3) . ? C27 H27 0.95(2) . ? C28 H28A 1.07(3) . ? C28 H28B 0.96(2) . ? 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 C14 C1 C2 105.2(2) . . ? C14 C1 H1A 110.7 . . ? C2 C1 H1A 110.7 . . ? C14 C1 H1B 110.7 . . ? C2 C1 H1B 110.7 . . ? H1A C1 H1B 108.8 . . ? C3 C2 C1 105.7(3) . . ? C3 C2 H2A 110.6 . . ? C1 C2 H2A 110.6 . . ? C3 C2 H2B 110.6 . . ? C1 C2 H2B 110.6 . . ? H2A C2 H2B 108.7 . . ? N4 C3 C2 103.1(3) . . ? N4 C3 H3A 111.2(16) . . ? C2 C3 H3A 117.3(16) . . ? N4 C3 H3B 106.9(17) . . ? C2 C3 H3B 114.5(17) . . ? H3A C3 H3B 104(2) . . ? C5 N4 C3 118.9(2) . . ? C5 N4 C14 127.84(18) . . ? C3 N4 C14 113.0(2) . . ? O15 C5 N4 121.9(2) . . ? O15 C5 C6 119.8(2) . . ? N4 C5 C6 117.40(19) . . ? N16 C6 C7 111.07(17) . . ? N16 C6 C5 116.5(2) . . ? C7 C6 C5 107.71(18) . . ? N16 C6 H6 110.7(12) . . ? C7 C6 H6 106.3(12) . . ? C5 C6 H6 103.9(12) . . ? C8 C7 C12 118.8(2) . . ? C8 C7 C6 120.4(2) . . ? C12 C7 C6 120.6(2) . . ? C9 C8 C7 121.1(3) . . ? C9 C8 H8 124.1(15) . . ? C7 C8 H8 114.8(15) . . ? C10 C9 C8 120.1(3) . . ? C10 C9 H9 120.9(14) . . ? C8 C9 H9 118.9(14) . . ? C9 C10 C11 119.6(3) . . ? C9 C10 H10 121.2(14) . . ? C11 C10 H10 119.1(14) . . ? C10 C11 C12 121.7(3) . . ? C10 C11 H11 119.4(12) . . ? C12 C11 H11 118.9(12) . . ? C11 C12 C7 118.6(2) . . ? C11 C12 C13 120.9(2) . . ? C7 C12 C13 120.45(19) . . ? C28 C13 C12 119.4(2) . . ? C28 C13 C14 120.7(2) . . ? C12 C13 C14 119.85(18) . . ? N4 C14 C1 101.4(2) . . ? N4 C14 C13 117.22(19) . . ? C1 C14 C13 111.34(19) . . ? N4 C14 H14 105.6(13) . . ? C1 C14 H14 109.8(14) . . ? C13 C14 H14 110.9(14) . . ? C17 N16 C6 118.16(18) . . ? C17 N16 C21 122.53(19) . . ? C6 N16 C21 116.22(19) . . ? O20 C17 N16 122.0(2) . . ? O20 C17 C18 121.1(2) . . ? N16 C17 C18 116.9(2) . . ? C19 C18 C17 112.7(2) . . ? C19 C18 H18A 109.0 . . ? C17 C18 H18A 109.0 . . ? C19 C18 H18B 109.0 . . ? C17 C18 H18B 109.0 . . ? H18A C18 H18B 107.8 . . ? C18 C19 H19A 109.5 . . ? C18 C19 H19B 109.5 . . ? H19A C19 H19B 109.5 . . ? C18 C19 H19C 109.5 . . ? H19A C19 H19C 109.5 . . ? H19B C19 H19C 109.5 . . ? N16 C21 C22 114.57(18) . . ? N16 C21 H21A 110.1(12) . . ? C22 C21 H21A 111.2(12) . . ? N16 C21 H21B 109.4(13) . . ? C22 C21 H21B 109.0(12) . . ? H21A C21 H21B 101.8(17) . . ? C23 C22 C27 118.8(2) . . ? C23 C22 C21 122.9(2) . . ? C27 C22 C21 118.3(2) . . ? C24 C23 C22 120.2(3) . . ? C24 C23 H23 119.1(11) . . ? C22 C23 H23 120.7(11) . . ? C25 C24 C23 120.3(3) . . ? C25 C24 H24 119.8 . . ? C23 C24 H24 119.8 . . ? C24 C25 C26 120.6(3) . . ? C24 C25 H25 124.4(16) . . ? C26 C25 H25 115.0(16) . . ? C25 C26 C27 119.9(3) . . ? C25 C26 H26 125.7(16) . . ? C27 C26 H26 114.3(16) . . ? C26 C27 C22 120.0(3) . . ? C26 C27 H27 122.4(15) . . ? C22 C27 H27 117.5(15) . . ? C13 C28 H28A 121.3(13) . . ? C13 C28 H28B 117.8(14) . . ? H28A C28 H28B 120.7(19) . . ? _diffrn_measured_fraction_theta_max 1.000 _diffrn_reflns_theta_full 28.00 _diffrn_measured_fraction_theta_full 1.000 _refine_diff_density_max 0.183 _refine_diff_density_min -0.140 _refine_diff_density_rms 0.032