Supplementary Material for Organic & Biomolecular Chemistry This journal is (c) The Royal Society of Chemistry 2008 data_global _journal_name_full Org.Biomol.Chem. _journal_coden_Cambridge 0177 _publ_contact_author_name 'Deevi Basavaiah' _publ_contact_author_address ; School of Chemistry University of Hyderabad Gachibowli Hyderabad Andhra Pradesh 500 046 INDIA ; _publ_contact_author_email DBSC@UOHYD.ERNET.IN _publ_section_title ; Simple and Facile Synthesis of Tetralone-Spiro-Glutarimides and Spiro-Bisglutarimides from the Baylis-Hillman Acetates ; loop_ _publ_author_name 'Deevi Basavaiah' 'Raju J. Reddy' # Attachment 'cif_files.cif' data_2e _database_code_depnum_ccdc_archive 'CCDC 656194' _audit_creation_method SHELXL-97 _chemical_name_systematic ; Di-tert-butyl 2,6-di[(E)-4-isopropylbenzylidene]- 4-cyano-4-phenyl-1,7-heptanedioate ; _chemical_name_common ; Di-tert-butyl 2,6-di((E)-4-isopropylbenzylidene)-4-cyano-4- phenyl-1,7-heptanedioate ; _chemical_melting_point 110(1) _chemical_formula_moiety 'C42 H51 N O4' _chemical_formula_sum 'C42 H51 N O4' _chemical_formula_weight 633.84 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 0.0000 '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 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0000 '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' 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 11.799(2) _cell_length_b 14.900(3) _cell_length_c 21.767(4) _cell_angle_alpha 90.00 _cell_angle_beta 98.298(3) _cell_angle_gamma 90.00 _cell_volume 3786.6(11) _cell_formula_units_Z 4 _cell_measurement_temperature 298 _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description rectangular _exptl_crystal_colour colorless _exptl_crystal_size_max 0.41 _exptl_crystal_size_mid 0.28 _exptl_crystal_size_min 0.16 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.112 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1368 _exptl_absorpt_coefficient_mu 0.070 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.9718 _exptl_absorpt_correction_T_max 0.9889 _exptl_absorpt_process_details 'SADABS-Bruker Nonius area detector scaling and absorption correction - V2.10' _exptl_special_details ; ? ; _diffrn_ambient_temperature 298 _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'CCD area detector' _diffrn_measurement_method 'phi and omega scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 26807 _diffrn_reflns_av_R_equivalents 0.0393 _diffrn_reflns_av_sigmaI/netI 0.0364 _diffrn_reflns_limit_h_min -14 _diffrn_reflns_limit_h_max 14 _diffrn_reflns_limit_k_min -17 _diffrn_reflns_limit_k_max 17 _diffrn_reflns_limit_l_min -25 _diffrn_reflns_limit_l_max 25 _diffrn_reflns_theta_min 1.66 _diffrn_reflns_theta_max 25.00 _reflns_number_total 6661 _reflns_number_gt 4163 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'Bruker SMART' _computing_data_reduction 'Bruker SAINT' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Ortep-3 for Windows/Platon' _computing_publication_material 'Bruker SHELXTL' _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^)+(0.0835P)^2^+0.4764P] 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 noref _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 6661 _refine_ls_number_parameters 434 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0970 _refine_ls_R_factor_gt 0.0580 _refine_ls_wR_factor_ref 0.1687 _refine_ls_wR_factor_gt 0.1491 _refine_ls_goodness_of_fit_ref 1.041 _refine_ls_restrained_S_all 1.041 _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 0.14819(15) 0.78785(12) 0.09048(10) 0.0882(6) Uani 1 1 d . . . O2 O 0.25799(12) 0.66975(10) 0.07592(7) 0.0567(4) Uani 1 1 d . . . O3 O 0.48819(19) 0.42440(12) 0.13727(9) 0.0896(6) Uani 1 1 d . . . O4 O 0.51572(13) 0.48630(10) 0.23178(7) 0.0581(4) Uani 1 1 d . . . N N 0.31526(18) 0.64241(15) 0.22550(10) 0.0717(6) Uani 1 1 d . . . C1 C 0.6527(3) 1.2466(2) 0.0907(2) 0.1220(14) Uani 1 1 d . . . H1A H 0.7054 1.2960 0.0972 0.183 Uiso 1 1 calc R . . H1B H 0.5790 1.2655 0.0996 0.183 Uiso 1 1 calc R . . H1C H 0.6461 1.2271 0.0483 0.183 Uiso 1 1 calc R . . C2 C 0.8113(3) 1.1414(2) 0.1217(2) 0.1283(14) Uani 1 1 d . . . H2A H 0.8096 1.1288 0.0783 0.192 Uiso 1 1 calc R . . H2B H 0.8334 1.0883 0.1454 0.192 Uiso 1 1 calc R . . H2C H 0.8655 1.1884 0.1339 0.192 Uiso 1 1 calc R . . C3 C 0.6960(3) 1.17029(19) 0.13321(17) 0.0894(9) Uani 1 1 d . . . H3 H 0.7036 1.1929 0.1759 0.107 Uiso 1 1 calc R . . C4 C 0.6066(2) 1.09458(17) 0.12737(13) 0.0721(7) Uani 1 1 d . . . C5 C 0.5204(3) 1.09425(17) 0.16391(15) 0.0814(8) Uani 1 1 d . . . H5 H 0.5187 1.1395 0.1932 0.098 Uiso 1 1 calc R . . C6 C 0.4370(2) 1.02925(16) 0.15839(14) 0.0762(8) Uani 1 1 d . . . H6 H 0.3793 1.0320 0.1833 0.091 Uiso 1 1 calc R . . C7 C 0.4376(2) 0.95990(15) 0.11645(12) 0.0604(6) Uani 1 1 d . . . C8 C 0.5232(2) 0.95949(17) 0.07937(12) 0.0727(7) Uani 1 1 d . . . H8 H 0.5257 0.9138 0.0505 0.087 Uiso 1 1 calc R . . C9 C 0.6053(3) 1.02650(19) 0.08485(13) 0.0799(8) Uani 1 1 d . . . H9 H 0.6613 1.0253 0.0589 0.096 Uiso 1 1 calc R . . C10 C 0.3450(2) 0.89245(15) 0.10896(11) 0.0599(6) Uani 1 1 d . . . H10 H 0.2710 0.9156 0.1047 0.072 Uiso 1 1 calc R . . C11 C 0.35182(18) 0.80343(14) 0.10737(10) 0.0479(5) Uani 1 1 d . . . C12 C 0.2411(2) 0.75449(15) 0.09129(11) 0.0539(6) Uani 1 1 d . . . C13 C 0.1620(2) 0.60733(17) 0.05671(13) 0.0671(7) Uani 1 1 d . . . C14 C 0.2251(3) 0.5215(2) 0.0477(3) 0.1456(18) Uani 1 1 d . . . H14A H 0.2752 0.5307 0.0172 0.218 Uiso 1 1 calc R . . H14B H 0.1709 0.4751 0.0338 0.218 Uiso 1 1 calc R . . H14C H 0.2693 0.5039 0.0863 0.218 Uiso 1 1 calc R . . C15 C 0.0890(3) 0.5968(2) 0.10707(15) 0.0956(10) Uani 1 1 d . . . H15A H 0.1360 0.5787 0.1448 0.143 Uiso 1 1 calc R . . H15B H 0.0316 0.5520 0.0952 0.143 Uiso 1 1 calc R . . H15C H 0.0527 0.6529 0.1136 0.143 Uiso 1 1 calc R . . C16 C 0.0923(3) 0.6409(2) -0.00261(15) 0.1016(11) Uani 1 1 d . . . H16A H 0.0560 0.6966 0.0054 0.152 Uiso 1 1 calc R . . H16B H 0.0349 0.5974 -0.0174 0.152 Uiso 1 1 calc R . . H16C H 0.1418 0.6502 -0.0334 0.152 Uiso 1 1 calc R . . C17 C 0.46085(17) 0.74963(14) 0.11960(9) 0.0463(5) Uani 1 1 d . . . H17A H 0.5231 0.7859 0.1085 0.056 Uiso 1 1 calc R . . H17B H 0.4534 0.6975 0.0926 0.056 Uiso 1 1 calc R . . C18 C 0.49350(17) 0.71715(14) 0.18776(9) 0.0446(5) Uani 1 1 d . . . C19 C 0.59425(17) 0.64871(13) 0.19322(10) 0.0469(5) Uani 1 1 d . . . H19A H 0.6624 0.6804 0.1852 0.056 Uiso 1 1 calc R . . H19B H 0.6085 0.6275 0.2358 0.056 Uiso 1 1 calc R . . C20 C 0.8675(6) 0.9160(3) -0.0064(2) 0.184(3) Uani 1 1 d . . . H20A H 0.9390 0.8963 0.0162 0.276 Uiso 1 1 calc R . . H20B H 0.8196 0.9389 0.0221 0.276 Uiso 1 1 calc R . . H20C H 0.8814 0.9625 -0.0349 0.276 Uiso 1 1 calc R . . C21 C 0.8487(4) 0.8126(3) -0.09659(17) 0.1339(15) Uani 1 1 d . . . H21A H 0.8730 0.8621 -0.1198 0.201 Uiso 1 1 calc R . . H21B H 0.7847 0.7833 -0.1207 0.201 Uiso 1 1 calc R . . H21C H 0.9106 0.7707 -0.0873 0.201 Uiso 1 1 calc R . . C22 C 0.8144(4) 0.8461(3) -0.03833(18) 0.1315(15) Uani 1 1 d . . . H22 H 0.7427 0.8758 -0.0554 0.158 Uiso 1 1 calc R . . C23 C 0.7657(3) 0.77168(19) -0.00187(13) 0.0791(8) Uani 1 1 d . . . C24 C 0.8148(2) 0.74556(19) 0.05666(13) 0.0745(8) Uani 1 1 d . . . H24 H 0.8816 0.7738 0.0749 0.089 Uiso 1 1 calc R . . C25 C 0.7677(2) 0.67842(18) 0.08914(12) 0.0641(7) Uani 1 1 d . . . H25 H 0.8026 0.6627 0.1287 0.077 Uiso 1 1 calc R . . C26 C 0.6690(2) 0.63466(14) 0.06303(10) 0.0520(6) Uani 1 1 d . . . C27 C 0.6223(2) 0.65864(18) 0.00339(11) 0.0686(7) Uani 1 1 d . . . H27 H 0.5577 0.6287 -0.0160 0.082 Uiso 1 1 calc R . . C28 C 0.6695(3) 0.7257(2) -0.02772(13) 0.0834(8) Uani 1 1 d . . . H28 H 0.6353 0.7407 -0.0676 0.100 Uiso 1 1 calc R . . C29 C 0.61229(19) 0.56463(15) 0.09522(10) 0.0540(6) Uani 1 1 d . . . H29 H 0.5983 0.5108 0.0738 0.065 Uiso 1 1 calc R . . C30 C 0.57817(18) 0.56802(13) 0.15094(10) 0.0462(5) Uani 1 1 d . . . C31 C 0.5216(2) 0.48508(15) 0.17150(11) 0.0542(6) Uani 1 1 d . . . C32 C 0.4614(2) 0.41305(16) 0.26358(12) 0.0657(7) Uani 1 1 d . . . C33 C 0.5284(3) 0.3282(2) 0.26101(18) 0.1057(11) Uani 1 1 d . . . H33A H 0.4979 0.2828 0.2853 0.159 Uiso 1 1 calc R . . H33B H 0.6072 0.3390 0.2774 0.159 Uiso 1 1 calc R . . H33C H 0.5231 0.3084 0.2187 0.159 Uiso 1 1 calc R . . C34 C 0.4705(4) 0.4484(2) 0.32855(15) 0.1249(15) Uani 1 1 d . . . H34A H 0.4323 0.5053 0.3282 0.187 Uiso 1 1 calc R . . H34B H 0.5498 0.4557 0.3454 0.187 Uiso 1 1 calc R . . H34C H 0.4353 0.4068 0.3537 0.187 Uiso 1 1 calc R . . C35 C 0.3387(3) 0.4020(2) 0.23557(18) 0.1104(12) Uani 1 1 d . . . H35A H 0.3008 0.3630 0.2613 0.166 Uiso 1 1 calc R . . H35B H 0.3349 0.3763 0.1949 0.166 Uiso 1 1 calc R . . H35C H 0.3016 0.4595 0.2326 0.166 Uiso 1 1 calc R . . C36 C 0.53049(18) 0.79616(14) 0.23152(10) 0.0495(5) Uani 1 1 d . . . C37 C 0.6263(2) 0.84614(16) 0.22267(12) 0.0664(7) Uani 1 1 d . . . H37 H 0.6654 0.8327 0.1897 0.080 Uiso 1 1 calc R . . C38 C 0.6640(2) 0.91570(18) 0.26247(15) 0.0807(8) Uani 1 1 d . . . H38 H 0.7288 0.9481 0.2564 0.097 Uiso 1 1 calc R . . C39 C 0.6065(3) 0.9370(2) 0.31057(15) 0.0914(10) Uani 1 1 d . . . H39 H 0.6318 0.9838 0.3374 0.110 Uiso 1 1 calc R . . C40 C 0.5115(3) 0.8890(2) 0.31883(14) 0.0896(9) Uani 1 1 d . . . H40 H 0.4719 0.9037 0.3514 0.108 Uiso 1 1 calc R . . C41 C 0.4735(2) 0.81951(17) 0.27994(11) 0.0638(7) Uani 1 1 d . . . H41 H 0.4084 0.7878 0.2864 0.077 Uiso 1 1 calc R . . C42 C 0.3926(2) 0.67367(15) 0.20818(10) 0.0504(5) Uani 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 O1 0.0485(10) 0.0672(12) 0.1470(19) -0.0221(12) 0.0082(11) 0.0076(9) O2 0.0468(9) 0.0470(9) 0.0755(11) -0.0130(8) 0.0060(8) -0.0032(7) O3 0.1376(18) 0.0603(12) 0.0710(12) -0.0146(10) 0.0153(11) -0.0360(11) O4 0.0704(11) 0.0489(9) 0.0571(10) -0.0011(7) 0.0161(8) -0.0125(8) N 0.0615(13) 0.0842(16) 0.0730(14) 0.0020(12) 0.0218(11) -0.0119(12) C1 0.101(3) 0.073(2) 0.192(4) 0.041(2) 0.018(2) -0.0115(18) C2 0.079(2) 0.099(3) 0.201(4) -0.016(3) 0.001(3) -0.011(2) C3 0.089(2) 0.0611(18) 0.119(3) 0.0005(17) 0.0174(19) -0.0138(16) C4 0.0851(19) 0.0480(15) 0.0815(19) 0.0026(13) 0.0063(15) -0.0090(13) C5 0.095(2) 0.0477(15) 0.103(2) -0.0146(15) 0.0205(18) -0.0056(15) C6 0.0858(19) 0.0457(15) 0.101(2) -0.0096(14) 0.0259(16) -0.0027(14) C7 0.0667(16) 0.0414(13) 0.0722(16) 0.0034(12) 0.0070(13) -0.0019(11) C8 0.097(2) 0.0539(15) 0.0692(17) -0.0051(13) 0.0205(15) -0.0183(14) C9 0.097(2) 0.0704(18) 0.0762(18) -0.0006(15) 0.0267(16) -0.0192(16) C10 0.0611(15) 0.0485(14) 0.0697(16) -0.0001(12) 0.0079(12) 0.0035(11) C11 0.0518(13) 0.0422(13) 0.0505(13) -0.0041(10) 0.0099(10) -0.0003(10) C12 0.0495(14) 0.0469(13) 0.0659(15) -0.0032(11) 0.0102(11) 0.0023(11) C13 0.0547(15) 0.0580(15) 0.0861(19) -0.0119(14) 0.0013(13) -0.0134(12) C14 0.088(2) 0.069(2) 0.273(5) -0.077(3) 0.004(3) -0.0115(18) C15 0.082(2) 0.099(2) 0.104(2) 0.0180(19) 0.0079(17) -0.0352(18) C16 0.091(2) 0.128(3) 0.080(2) -0.0081(19) -0.0096(17) -0.042(2) C17 0.0475(12) 0.0436(12) 0.0494(12) -0.0054(10) 0.0126(10) -0.0049(10) C18 0.0449(12) 0.0445(12) 0.0459(12) -0.0062(9) 0.0116(9) -0.0039(9) C19 0.0489(12) 0.0452(12) 0.0472(12) -0.0018(10) 0.0095(10) -0.0025(10) C20 0.311(7) 0.119(4) 0.128(4) 0.013(3) 0.057(4) -0.098(4) C21 0.186(4) 0.134(3) 0.099(3) 0.018(2) 0.077(3) -0.022(3) C22 0.189(4) 0.121(3) 0.097(3) 0.001(2) 0.063(3) -0.066(3) C23 0.105(2) 0.0788(19) 0.0595(17) -0.0018(14) 0.0328(16) -0.0138(17) C24 0.0657(16) 0.090(2) 0.0716(19) -0.0101(15) 0.0221(14) -0.0182(15) C25 0.0585(15) 0.0785(17) 0.0573(15) 0.0031(13) 0.0148(12) 0.0011(14) C26 0.0591(14) 0.0502(13) 0.0495(13) -0.0068(11) 0.0173(11) 0.0043(11) C27 0.0800(18) 0.0770(18) 0.0502(15) -0.0067(13) 0.0138(13) -0.0092(14) C28 0.108(2) 0.091(2) 0.0505(15) 0.0060(15) 0.0113(15) -0.0113(19) C29 0.0592(14) 0.0477(13) 0.0555(14) -0.0100(11) 0.0099(11) 0.0034(11) C30 0.0491(13) 0.0409(12) 0.0482(13) -0.0032(10) 0.0057(10) 0.0024(10) C31 0.0635(15) 0.0440(13) 0.0551(15) -0.0046(11) 0.0087(11) -0.0031(11) C32 0.0753(18) 0.0523(15) 0.0728(17) 0.0073(12) 0.0221(14) -0.0157(13) C33 0.123(3) 0.067(2) 0.134(3) 0.0381(19) 0.045(2) 0.0109(19) C34 0.199(4) 0.107(3) 0.080(2) -0.0048(19) 0.060(2) -0.064(3) C35 0.078(2) 0.112(3) 0.143(3) 0.033(2) 0.021(2) -0.0278(19) C36 0.0512(13) 0.0466(13) 0.0493(13) -0.0077(10) 0.0025(10) 0.0031(10) C37 0.0632(16) 0.0586(16) 0.0773(17) -0.0193(13) 0.0100(13) -0.0073(13) C38 0.0693(18) 0.0608(17) 0.108(2) -0.0242(16) 0.0002(16) -0.0103(14) C39 0.109(3) 0.0690(19) 0.090(2) -0.0400(17) -0.0082(19) -0.0031(18) C40 0.114(3) 0.080(2) 0.0752(19) -0.0347(17) 0.0178(18) 0.0029(19) C41 0.0721(16) 0.0605(15) 0.0600(15) -0.0139(12) 0.0136(13) 0.0026(13) C42 0.0520(14) 0.0521(13) 0.0479(13) -0.0062(10) 0.0103(11) -0.0031(11) _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 C12 1.202(3) . ? O2 C12 1.328(3) . ? O2 C13 1.479(3) . ? O3 C31 1.201(3) . ? O4 C31 1.324(3) . ? O4 C32 1.486(3) . ? N C42 1.136(3) . ? C1 C3 1.508(4) . ? C1 H1A 0.9600 . ? C1 H1B 0.9600 . ? C1 H1C 0.9600 . ? C2 C3 1.482(4) . ? C2 H2A 0.9600 . ? C2 H2B 0.9600 . ? C2 H2C 0.9600 . ? C3 C4 1.536(4) . ? C3 H3 0.9800 . ? C4 C9 1.372(4) . ? C4 C5 1.379(4) . ? C5 C6 1.374(4) . ? C5 H5 0.9300 . ? C6 C7 1.380(3) . ? C6 H6 0.9300 . ? C7 C8 1.381(3) . ? C7 C10 1.476(3) . ? C8 C9 1.384(4) . ? C8 H8 0.9300 . ? C9 H9 0.9300 . ? C10 C11 1.330(3) . ? C10 H10 0.9300 . ? C11 C12 1.493(3) . ? C11 C17 1.506(3) . ? C13 C15 1.497(4) . ? C13 C14 1.507(4) . ? C13 C16 1.512(4) . ? C14 H14A 0.9600 . ? C14 H14B 0.9600 . ? C14 H14C 0.9600 . ? C15 H15A 0.9600 . ? C15 H15B 0.9600 . ? C15 H15C 0.9600 . ? C16 H16A 0.9600 . ? C16 H16B 0.9600 . ? C16 H16C 0.9600 . ? C17 C18 1.555(3) . ? C17 H17A 0.9700 . ? C17 H17B 0.9700 . ? C18 C42 1.479(3) . ? C18 C36 1.537(3) . ? C18 C19 1.558(3) . ? C19 C30 1.509(3) . ? C19 H19A 0.9700 . ? C19 H19B 0.9700 . ? C20 C22 1.355(5) . ? C20 H20A 0.9600 . ? C20 H20B 0.9600 . ? C20 H20C 0.9600 . ? C21 C22 1.472(5) . ? C21 H21A 0.9600 . ? C21 H21B 0.9600 . ? C21 H21C 0.9600 . ? C22 C23 1.523(4) . ? C22 H22 0.9800 . ? C23 C28 1.374(4) . ? C23 C24 1.378(4) . ? C24 C25 1.387(3) . ? C24 H24 0.9300 . ? C25 C26 1.383(3) . ? C25 H25 0.9300 . ? C26 C27 1.382(3) . ? C26 C29 1.471(3) . ? C27 C28 1.370(4) . ? C27 H27 0.9300 . ? C28 H28 0.9300 . ? C29 C30 1.333(3) . ? C29 H29 0.9300 . ? C30 C31 1.503(3) . ? C32 C35 1.497(4) . ? C32 C33 1.497(4) . ? C32 C34 1.498(4) . ? C33 H33A 0.9600 . ? C33 H33B 0.9600 . ? C33 H33C 0.9600 . ? C34 H34A 0.9600 . ? C34 H34B 0.9600 . ? C34 H34C 0.9600 . ? C35 H35A 0.9600 . ? C35 H35B 0.9600 . ? C35 H35C 0.9600 . ? C36 C41 1.374(3) . ? C36 C37 1.390(3) . ? C37 C38 1.382(3) . ? C37 H37 0.9300 . ? C38 C39 1.364(4) . ? C38 H38 0.9300 . ? C39 C40 1.363(4) . ? C39 H39 0.9300 . ? C40 C41 1.372(4) . ? C40 H40 0.9300 . ? C41 H41 0.9300 . ? 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 C12 O2 C13 122.18(17) . . ? C31 O4 C32 122.62(18) . . ? C3 C1 H1A 109.5 . . ? C3 C1 H1B 109.5 . . ? H1A C1 H1B 109.5 . . ? C3 C1 H1C 109.5 . . ? H1A C1 H1C 109.5 . . ? H1B C1 H1C 109.5 . . ? C3 C2 H2A 109.5 . . ? C3 C2 H2B 109.5 . . ? H2A C2 H2B 109.5 . . ? C3 C2 H2C 109.5 . . ? H2A C2 H2C 109.5 . . ? H2B C2 H2C 109.5 . . ? C2 C3 C1 110.7(3) . . ? C2 C3 C4 114.1(3) . . ? C1 C3 C4 109.6(3) . . ? C2 C3 H3 107.4 . . ? C1 C3 H3 107.4 . . ? C4 C3 H3 107.4 . . ? C9 C4 C5 116.7(2) . . ? C9 C4 C3 122.7(3) . . ? C5 C4 C3 120.6(3) . . ? C6 C5 C4 122.1(3) . . ? C6 C5 H5 119.0 . . ? C4 C5 H5 119.0 . . ? C5 C6 C7 120.9(3) . . ? C5 C6 H6 119.5 . . ? C7 C6 H6 119.5 . . ? C6 C7 C8 117.6(2) . . ? C6 C7 C10 120.6(2) . . ? C8 C7 C10 121.6(2) . . ? C7 C8 C9 120.6(2) . . ? C7 C8 H8 119.7 . . ? C9 C8 H8 119.7 . . ? C4 C9 C8 122.1(3) . . ? C4 C9 H9 119.0 . . ? C8 C9 H9 119.0 . . ? C11 C10 C7 129.4(2) . . ? C11 C10 H10 115.3 . . ? C7 C10 H10 115.3 . . ? C10 C11 C12 116.0(2) . . ? C10 C11 C17 125.4(2) . . ? C12 C11 C17 118.51(18) . . ? O1 C12 O2 124.0(2) . . ? O1 C12 C11 124.5(2) . . ? O2 C12 C11 111.45(18) . . ? O2 C13 C15 110.9(2) . . ? O2 C13 C14 101.4(2) . . ? C15 C13 C14 110.7(3) . . ? O2 C13 C16 109.4(2) . . ? C15 C13 C16 111.2(2) . . ? C14 C13 C16 112.8(3) . . ? C13 C14 H14A 109.5 . . ? C13 C14 H14B 109.5 . . ? H14A C14 H14B 109.5 . . ? C13 C14 H14C 109.5 . . ? H14A C14 H14C 109.5 . . ? H14B C14 H14C 109.5 . . ? C13 C15 H15A 109.5 . . ? C13 C15 H15B 109.5 . . ? H15A C15 H15B 109.5 . . ? C13 C15 H15C 109.5 . . ? H15A C15 H15C 109.5 . . ? H15B C15 H15C 109.5 . . ? C13 C16 H16A 109.5 . . ? C13 C16 H16B 109.5 . . ? H16A C16 H16B 109.5 . . ? C13 C16 H16C 109.5 . . ? H16A C16 H16C 109.5 . . ? H16B C16 H16C 109.5 . . ? C11 C17 C18 114.95(16) . . ? C11 C17 H17A 108.5 . . ? C18 C17 H17A 108.5 . . ? C11 C17 H17B 108.5 . . ? C18 C17 H17B 108.5 . . ? H17A C17 H17B 107.5 . . ? C42 C18 C36 108.54(16) . . ? C42 C18 C17 108.89(17) . . ? C36 C18 C17 111.22(17) . . ? C42 C18 C19 109.19(17) . . ? C36 C18 C19 107.98(16) . . ? C17 C18 C19 110.97(15) . . ? C30 C19 C18 116.58(17) . . ? C30 C19 H19A 108.1 . . ? C18 C19 H19A 108.1 . . ? C30 C19 H19B 108.1 . . ? C18 C19 H19B 108.1 . . ? H19A C19 H19B 107.3 . . ? C22 C20 H20A 109.5 . . ? C22 C20 H20B 109.5 . . ? H20A C20 H20B 109.5 . . ? C22 C20 H20C 109.5 . . ? H20A C20 H20C 109.5 . . ? H20B C20 H20C 109.5 . . ? C22 C21 H21A 109.5 . . ? C22 C21 H21B 109.5 . . ? H21A C21 H21B 109.5 . . ? C22 C21 H21C 109.5 . . ? H21A C21 H21C 109.5 . . ? H21B C21 H21C 109.5 . . ? C20 C22 C21 122.6(4) . . ? C20 C22 C23 118.3(3) . . ? C21 C22 C23 111.9(3) . . ? C20 C22 H22 99.0 . . ? C21 C22 H22 99.0 . . ? C23 C22 H22 99.0 . . ? C28 C23 C24 116.8(3) . . ? C28 C23 C22 120.0(3) . . ? C24 C23 C22 123.2(3) . . ? C23 C24 C25 121.9(3) . . ? C23 C24 H24 119.0 . . ? C25 C24 H24 119.0 . . ? C26 C25 C24 120.4(2) . . ? C26 C25 H25 119.8 . . ? C24 C25 H25 119.8 . . ? C27 C26 C25 117.5(2) . . ? C27 C26 C29 118.9(2) . . ? C25 C26 C29 123.6(2) . . ? C28 C27 C26 121.2(3) . . ? C28 C27 H27 119.4 . . ? C26 C27 H27 119.4 . . ? C27 C28 C23 122.1(3) . . ? C27 C28 H28 118.9 . . ? C23 C28 H28 118.9 . . ? C30 C29 C26 128.7(2) . . ? C30 C29 H29 115.7 . . ? C26 C29 H29 115.7 . . ? C29 C30 C31 116.44(19) . . ? C29 C30 C19 123.86(19) . . ? C31 C30 C19 119.70(18) . . ? O3 C31 O4 124.5(2) . . ? O3 C31 C30 123.6(2) . . ? O4 C31 C30 111.88(19) . . ? O4 C32 C35 110.4(2) . . ? O4 C32 C33 109.7(2) . . ? C35 C32 C33 112.2(3) . . ? O4 C32 C34 101.8(2) . . ? C35 C32 C34 110.9(3) . . ? C33 C32 C34 111.4(3) . . ? C32 C33 H33A 109.5 . . ? C32 C33 H33B 109.5 . . ? H33A C33 H33B 109.5 . . ? C32 C33 H33C 109.5 . . ? H33A C33 H33C 109.5 . . ? H33B C33 H33C 109.5 . . ? C32 C34 H34A 109.5 . . ? C32 C34 H34B 109.5 . . ? H34A C34 H34B 109.5 . . ? C32 C34 H34C 109.5 . . ? H34A C34 H34C 109.5 . . ? H34B C34 H34C 109.5 . . ? C32 C35 H35A 109.5 . . ? C32 C35 H35B 109.5 . . ? H35A C35 H35B 109.5 . . ? C32 C35 H35C 109.5 . . ? H35A C35 H35C 109.5 . . ? H35B C35 H35C 109.5 . . ? C41 C36 C37 117.9(2) . . ? C41 C36 C18 122.9(2) . . ? C37 C36 C18 119.22(19) . . ? C38 C37 C36 120.6(2) . . ? C38 C37 H37 119.7 . . ? C36 C37 H37 119.7 . . ? C39 C38 C37 120.3(3) . . ? C39 C38 H38 119.8 . . ? C37 C38 H38 119.8 . . ? C40 C39 C38 119.2(3) . . ? C40 C39 H39 120.4 . . ? C38 C39 H39 120.4 . . ? C39 C40 C41 121.1(3) . . ? C39 C40 H40 119.4 . . ? C41 C40 H40 119.4 . . ? C40 C41 C36 120.8(3) . . ? C40 C41 H41 119.6 . . ? C36 C41 H41 119.6 . . ? N C42 C18 177.6(2) . . ? _diffrn_measured_fraction_theta_max 1.000 _diffrn_reflns_theta_full 25.00 _diffrn_measured_fraction_theta_full 1.000 _refine_diff_density_max 0.258 _refine_diff_density_min -0.237 _refine_diff_density_rms 0.035 ###END### data_3a _database_code_depnum_ccdc_archive 'CCDC 656195' _audit_creation_method SHELXL-97 _chemical_name_systematic ; 2,5'-Di[(E)-benzylidene]-[1,2,3,4-tetrahydronaphthalen-1-one] 4-spiro-3'-[piperidine-2',6'-dione] ; _chemical_name_common ; 2,5'-Di((E)-benzylidene)-(1,2,3,4-tetrahydronaphthalen-1-one) 4-spiro-3'-(piperidine-2',6'-dione) ; _chemical_melting_point 184(2) _chemical_formula_moiety 'C28 H21 N O3' _chemical_formula_sum 'C28 H21 N O3' _chemical_formula_weight 419.46 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 0.0000 '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 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0000 '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' 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 9.0369(18) _cell_length_b 25.751(5) _cell_length_c 9.2740(18) _cell_angle_alpha 90.00 _cell_angle_beta 96.108(3) _cell_angle_gamma 90.00 _cell_volume 2145.9(7) _cell_formula_units_Z 4 _cell_measurement_temperature 298 _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description Block _exptl_crystal_colour colorless _exptl_crystal_size_max 0.44 _exptl_crystal_size_mid 0.28 _exptl_crystal_size_min 0.22 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.298 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 880 _exptl_absorpt_coefficient_mu 0.084 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.9639 _exptl_absorpt_correction_T_max 0.9817 _exptl_absorpt_process_details 'SADABS-Bruker Nonius area detector scaling and absorption correction - V2.10' _exptl_special_details ; ? ; _diffrn_ambient_temperature 298 _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'CCD area detector' _diffrn_measurement_method 'phi and omega scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 12584 _diffrn_reflns_av_R_equivalents 0.0233 _diffrn_reflns_av_sigmaI/netI 0.0235 _diffrn_reflns_limit_h_min -10 _diffrn_reflns_limit_h_max 9 _diffrn_reflns_limit_k_min -22 _diffrn_reflns_limit_k_max 30 _diffrn_reflns_limit_l_min -11 _diffrn_reflns_limit_l_max 11 _diffrn_reflns_theta_min 1.58 _diffrn_reflns_theta_max 25.00 _reflns_number_total 3780 _reflns_number_gt 3097 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'Bruker SMART' _computing_data_reduction 'Bruker SAINT' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Ortep-3 for Windows/Platon' _computing_publication_material 'Bruker SHELXTL' _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^)+(0.0526P)^2^+0.3438P] 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 none _refine_ls_extinction_coef ? _refine_ls_number_reflns 3780 _refine_ls_number_parameters 293 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0528 _refine_ls_R_factor_gt 0.0427 _refine_ls_wR_factor_ref 0.1081 _refine_ls_wR_factor_gt 0.1031 _refine_ls_goodness_of_fit_ref 1.065 _refine_ls_restrained_S_all 1.065 _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 0.39665(14) 0.24285(5) 0.50025(11) 0.0598(3) Uani 1 1 d . . . O2 O 0.49069(18) 0.12690(5) -0.27763(12) 0.0782(5) Uani 1 1 d . . . O3 O 0.30426(14) 0.27618(5) -0.13502(12) 0.0593(3) Uani 1 1 d . . . N1 N 0.42346(17) 0.20494(5) -0.19979(14) 0.0509(4) Uani 1 1 d . . . H1N H 0.391(2) 0.2122(7) -0.289(2) 0.063(5) Uiso 1 1 d . . . C1 C 0.47677(16) 0.27852(6) 0.14098(15) 0.0365(3) Uani 1 1 d . . . C2 C 0.54705(18) 0.31880(6) 0.07548(17) 0.0476(4) Uani 1 1 d . . . H2 H 0.5679 0.3153 -0.0201 0.057 Uiso 1 1 calc R . . C3 C 0.5863(2) 0.36387(7) 0.14994(18) 0.0545(4) Uani 1 1 d . . . H3 H 0.6336 0.3903 0.1044 0.065 Uiso 1 1 calc R . . C4 C 0.5558(2) 0.37006(7) 0.29200(19) 0.0549(4) Uani 1 1 d . . . H4 H 0.5799 0.4009 0.3411 0.066 Uiso 1 1 calc R . . C5 C 0.48978(19) 0.33039(6) 0.35948(17) 0.0491(4) Uani 1 1 d . . . H5 H 0.4700 0.3343 0.4553 0.059 Uiso 1 1 calc R . . C6 C 0.45169(16) 0.28408(6) 0.28601(15) 0.0385(3) Uani 1 1 d . . . C7 C 0.39629(17) 0.24011(6) 0.36840(15) 0.0412(4) Uani 1 1 d . . . C8 C 0.34355(16) 0.19314(6) 0.28565(15) 0.0390(4) Uani 1 1 d . . . C9 C 0.30708(16) 0.20082(6) 0.12478(15) 0.0398(4) Uani 1 1 d . . . H9A H 0.2178 0.2218 0.1066 0.048 Uiso 1 1 calc R . . H9B H 0.2881 0.1674 0.0781 0.048 Uiso 1 1 calc R . . C10 C 0.43802(16) 0.22812(5) 0.06016(14) 0.0355(3) Uani 1 1 d . . . C11 C 0.57626(16) 0.19305(5) 0.07213(15) 0.0378(3) Uani 1 1 d . . . H11A H 0.6614 0.2135 0.0507 0.045 Uiso 1 1 calc R . . H11B H 0.5956 0.1808 0.1713 0.045 Uiso 1 1 calc R . . C12 C 0.56164(17) 0.14702(6) -0.02759(15) 0.0400(4) Uani 1 1 d . . . C13 C 0.4915(2) 0.15711(6) -0.17703(16) 0.0505(4) Uani 1 1 d . . . C14 C 0.38294(18) 0.23969(6) -0.09845(15) 0.0413(4) Uani 1 1 d . . . C15 C 0.60714(18) 0.09839(6) 0.00085(16) 0.0456(4) Uani 1 1 d . . . H15 H 0.5895 0.0759 -0.0777 0.055 Uiso 1 1 calc R . . C16 C 0.67950(17) 0.07368(6) 0.13197(16) 0.0436(4) Uani 1 1 d . . . C17 C 0.67223(19) 0.01965(6) 0.13899(18) 0.0516(4) Uani 1 1 d . . . H17 H 0.6271 0.0014 0.0597 0.062 Uiso 1 1 calc R . . C18 C 0.7300(2) -0.00720(7) 0.2599(2) 0.0605(5) Uani 1 1 d . . . H18 H 0.7215 -0.0432 0.2628 0.073 Uiso 1 1 calc R . . C19 C 0.8002(2) 0.01886(8) 0.3763(2) 0.0648(5) Uani 1 1 d . . . H19 H 0.8396 0.0007 0.4583 0.078 Uiso 1 1 calc R . . C20 C 0.8120(2) 0.07170(8) 0.3712(2) 0.0658(5) Uani 1 1 d . . . H20 H 0.8599 0.0893 0.4504 0.079 Uiso 1 1 calc R . . C21 C 0.75387(19) 0.09951(7) 0.25040(18) 0.0551(5) Uani 1 1 d . . . H21 H 0.7645 0.1354 0.2483 0.066 Uiso 1 1 calc R . . C22 C 0.34326(17) 0.14801(6) 0.35716(15) 0.0438(4) Uani 1 1 d . . . H22 H 0.3798 0.1491 0.4547 0.053 Uiso 1 1 calc R . . C23 C 0.29286(18) 0.09705(6) 0.30151(16) 0.0447(4) Uani 1 1 d . . . C24 C 0.1597(2) 0.09059(7) 0.21246(18) 0.0560(4) Uani 1 1 d . . . H24 H 0.1022 0.1195 0.1837 0.067 Uiso 1 1 calc R . . C25 C 0.1125(2) 0.04197(8) 0.1667(2) 0.0674(5) Uani 1 1 d . . . H25 H 0.0231 0.0382 0.1081 0.081 Uiso 1 1 calc R . . C26 C 0.1968(2) -0.00108(8) 0.2073(2) 0.0695(6) Uani 1 1 d . . . H26 H 0.1648 -0.0339 0.1756 0.083 Uiso 1 1 calc R . . C27 C 0.3281(2) 0.00438(8) 0.2947(2) 0.0667(5) Uani 1 1 d . . . H27 H 0.3857 -0.0247 0.3212 0.080 Uiso 1 1 calc R . . C28 C 0.3751(2) 0.05295(7) 0.34323(18) 0.0556(4) Uani 1 1 d . . . H28 H 0.4628 0.0562 0.4047 0.067 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 0.0900(9) 0.0599(8) 0.0300(6) -0.0007(5) 0.0096(5) 0.0012(6) O2 0.1331(13) 0.0597(8) 0.0379(7) -0.0160(6) -0.0095(7) 0.0206(8) O3 0.0823(9) 0.0497(7) 0.0418(6) 0.0040(5) -0.0121(6) 0.0155(6) N1 0.0808(10) 0.0445(8) 0.0254(6) 0.0014(6) -0.0040(6) 0.0049(7) C1 0.0399(8) 0.0342(8) 0.0339(7) 0.0002(6) -0.0027(6) 0.0034(6) C2 0.0605(10) 0.0417(9) 0.0405(8) 0.0001(7) 0.0043(7) -0.0056(8) C3 0.0641(11) 0.0416(10) 0.0562(10) 0.0011(8) -0.0004(8) -0.0098(8) C4 0.0680(12) 0.0370(9) 0.0573(10) -0.0104(8) -0.0046(8) -0.0017(8) C5 0.0598(10) 0.0461(10) 0.0399(8) -0.0083(7) -0.0012(7) 0.0074(8) C6 0.0431(8) 0.0370(8) 0.0341(7) -0.0025(6) -0.0021(6) 0.0066(7) C7 0.0455(9) 0.0469(9) 0.0309(7) -0.0002(6) 0.0024(6) 0.0068(7) C8 0.0398(8) 0.0438(9) 0.0336(7) 0.0021(6) 0.0053(6) -0.0002(7) C9 0.0419(8) 0.0428(9) 0.0337(7) 0.0007(6) -0.0011(6) -0.0026(7) C10 0.0433(8) 0.0344(8) 0.0277(7) 0.0002(6) -0.0009(6) -0.0025(6) C11 0.0434(8) 0.0370(8) 0.0323(7) -0.0014(6) 0.0012(6) -0.0006(7) C12 0.0490(9) 0.0376(9) 0.0333(7) -0.0021(6) 0.0035(6) -0.0016(7) C13 0.0744(12) 0.0423(10) 0.0338(8) -0.0030(7) 0.0009(7) 0.0020(8) C14 0.0541(9) 0.0368(8) 0.0314(7) 0.0029(6) -0.0022(6) -0.0037(7) C15 0.0573(10) 0.0393(9) 0.0390(8) -0.0058(7) 0.0000(7) 0.0004(7) C16 0.0465(9) 0.0394(9) 0.0444(8) -0.0019(7) 0.0030(7) 0.0033(7) C17 0.0551(10) 0.0412(10) 0.0578(10) -0.0015(8) 0.0021(8) 0.0034(8) C18 0.0609(11) 0.0487(11) 0.0722(12) 0.0131(9) 0.0081(9) 0.0098(9) C19 0.0635(12) 0.0737(14) 0.0569(11) 0.0173(10) 0.0043(9) 0.0200(10) C20 0.0655(12) 0.0735(14) 0.0545(11) -0.0054(9) -0.0116(9) 0.0144(10) C21 0.0571(10) 0.0469(10) 0.0581(10) -0.0058(8) -0.0085(8) 0.0067(8) C22 0.0483(9) 0.0506(10) 0.0328(7) 0.0031(7) 0.0052(6) -0.0022(7) C23 0.0517(9) 0.0474(10) 0.0364(8) 0.0051(7) 0.0109(7) -0.0060(8) C24 0.0532(10) 0.0576(11) 0.0571(10) 0.0045(8) 0.0053(8) -0.0069(9) C25 0.0625(12) 0.0749(15) 0.0649(12) -0.0077(10) 0.0073(9) -0.0206(11) C26 0.0835(15) 0.0583(13) 0.0704(12) -0.0135(10) 0.0257(11) -0.0211(11) C27 0.0839(15) 0.0484(11) 0.0704(12) 0.0033(9) 0.0211(11) 0.0007(10) C28 0.0610(11) 0.0527(11) 0.0531(10) 0.0077(8) 0.0063(8) -0.0009(9) _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 C7 1.2245(17) . ? O2 C13 1.2142(19) . ? O3 C14 1.2051(18) . ? N1 C14 1.375(2) . ? N1 C13 1.383(2) . ? N1 H1N 0.872(19) . ? C1 C2 1.389(2) . ? C1 C6 1.395(2) . ? C1 C10 1.5210(19) . ? C2 C3 1.377(2) . ? C2 H2 0.9300 . ? C3 C4 1.384(2) . ? C3 H3 0.9300 . ? C4 C5 1.368(2) . ? C4 H4 0.9300 . ? C5 C6 1.398(2) . ? C5 H5 0.9300 . ? C6 C7 1.482(2) . ? C7 C8 1.484(2) . ? C8 C22 1.338(2) . ? C8 C9 1.5063(19) . ? C9 C10 1.551(2) . ? C9 H9A 0.9700 . ? C9 H9B 0.9700 . ? C10 C14 1.5312(18) . ? C10 C11 1.536(2) . ? C11 C12 1.5007(19) . ? C11 H11A 0.9700 . ? C11 H11B 0.9700 . ? C12 C15 1.336(2) . ? C12 C13 1.484(2) . ? C15 C16 1.464(2) . ? C15 H15 0.9300 . ? C16 C21 1.394(2) . ? C16 C17 1.395(2) . ? C17 C18 1.373(2) . ? C17 H17 0.9300 . ? C18 C19 1.368(3) . ? C18 H18 0.9300 . ? C19 C20 1.366(3) . ? C19 H19 0.9300 . ? C20 C21 1.385(2) . ? C20 H20 0.9300 . ? C21 H21 0.9300 . ? C22 C23 1.465(2) . ? C22 H22 0.9300 . ? C23 C28 1.389(2) . ? C23 C24 1.395(2) . ? C24 C25 1.375(2) . ? C24 H24 0.9300 . ? C25 C26 1.375(3) . ? C25 H25 0.9300 . ? C26 C27 1.371(3) . ? C26 H26 0.9300 . ? C27 C28 1.381(3) . ? C27 H27 0.9300 . ? C28 H28 0.9300 . ? 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 N1 C13 128.44(13) . . ? C14 N1 H1N 115.2(12) . . ? C13 N1 H1N 115.8(12) . . ? C2 C1 C6 118.28(13) . . ? C2 C1 C10 120.91(13) . . ? C6 C1 C10 120.68(13) . . ? C3 C2 C1 121.00(15) . . ? C3 C2 H2 119.5 . . ? C1 C2 H2 119.5 . . ? C2 C3 C4 120.52(16) . . ? C2 C3 H3 119.7 . . ? C4 C3 H3 119.7 . . ? C5 C4 C3 119.36(15) . . ? C5 C4 H4 120.3 . . ? C3 C4 H4 120.3 . . ? C4 C5 C6 120.72(15) . . ? C4 C5 H5 119.6 . . ? C6 C5 H5 119.6 . . ? C1 C6 C5 120.03(14) . . ? C1 C6 C7 121.13(13) . . ? C5 C6 C7 118.65(13) . . ? O1 C7 C6 120.37(14) . . ? O1 C7 C8 122.00(14) . . ? C6 C7 C8 117.62(12) . . ? C22 C8 C7 117.98(13) . . ? C22 C8 C9 126.38(14) . . ? C7 C8 C9 115.45(13) . . ? C8 C9 C10 110.29(11) . . ? C8 C9 H9A 109.6 . . ? C10 C9 H9A 109.6 . . ? C8 C9 H9B 109.6 . . ? C10 C9 H9B 109.6 . . ? H9A C9 H9B 108.1 . . ? C1 C10 C14 109.97(11) . . ? C1 C10 C11 108.86(11) . . ? C14 C10 C11 111.26(12) . . ? C1 C10 C9 109.97(12) . . ? C14 C10 C9 106.02(11) . . ? C11 C10 C9 110.73(12) . . ? C12 C11 C10 113.72(12) . . ? C12 C11 H11A 108.8 . . ? C10 C11 H11A 108.8 . . ? C12 C11 H11B 108.8 . . ? C10 C11 H11B 108.8 . . ? H11A C11 H11B 107.7 . . ? C15 C12 C13 116.13(13) . . ? C15 C12 C11 127.87(13) . . ? C13 C12 C11 115.98(13) . . ? O2 C13 N1 119.15(14) . . ? O2 C13 C12 124.93(15) . . ? N1 C13 C12 115.93(13) . . ? O3 C14 N1 120.47(13) . . ? O3 C14 C10 122.95(14) . . ? N1 C14 C10 116.55(13) . . ? C12 C15 C16 132.28(14) . . ? C12 C15 H15 113.9 . . ? C16 C15 H15 113.9 . . ? C21 C16 C17 117.41(15) . . ? C21 C16 C15 125.63(15) . . ? C17 C16 C15 116.96(14) . . ? C18 C17 C16 121.67(16) . . ? C18 C17 H17 119.2 . . ? C16 C17 H17 119.2 . . ? C19 C18 C17 120.10(18) . . ? C19 C18 H18 120.0 . . ? C17 C18 H18 120.0 . . ? C20 C19 C18 119.53(17) . . ? C20 C19 H19 120.2 . . ? C18 C19 H19 120.2 . . ? C19 C20 C21 121.23(18) . . ? C19 C20 H20 119.4 . . ? C21 C20 H20 119.4 . . ? C20 C21 C16 120.01(17) . . ? C20 C21 H21 120.0 . . ? C16 C21 H21 120.0 . . ? C8 C22 C23 128.34(14) . . ? C8 C22 H22 115.8 . . ? C23 C22 H22 115.8 . . ? C28 C23 C24 117.99(16) . . ? C28 C23 C22 119.81(15) . . ? C24 C23 C22 122.12(15) . . ? C25 C24 C23 120.71(18) . . ? C25 C24 H24 119.6 . . ? C23 C24 H24 119.6 . . ? C26 C25 C24 120.35(18) . . ? C26 C25 H25 119.8 . . ? C24 C25 H25 119.8 . . ? C27 C26 C25 119.91(19) . . ? C27 C26 H26 120.0 . . ? C25 C26 H26 120.0 . . ? C26 C27 C28 120.14(19) . . ? C26 C27 H27 119.9 . . ? C28 C27 H27 119.9 . . ? C27 C28 C23 120.87(17) . . ? C27 C28 H28 119.6 . . ? C23 C28 H28 119.6 . . ? _diffrn_measured_fraction_theta_max 1.000 _diffrn_reflns_theta_full 25.00 _diffrn_measured_fraction_theta_full 1.000 _refine_diff_density_max 0.197 _refine_diff_density_min -0.282 _refine_diff_density_rms 0.044 ###END### data_3f _database_code_depnum_ccdc_archive 'CCDC 656196' _audit_creation_method SHELXL-97 _chemical_name_systematic ; 2,5'-Di[(E)-2-chlorobenzylidene]-[1,2,3,4-tetrahydronaphthalen-1-one] 4-spiro-3'-[piperidine-2',6'-dione] ; _chemical_name_common ; 2,5'-Di((E)-2-chlorobenzylidene)-(1,2,3,4- tetrahydronaphthalen-1-one) 4-spiro-3'-(piperidine-2',6'-dione) ; _chemical_melting_point 187(2) _chemical_formula_moiety 'C28 H19 Cl2 N O3' _chemical_formula_sum 'C28 H19 Cl2 N O3' _chemical_formula_weight 488.34 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 0.0000 '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' Cl Cl 0.1484 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Triclinic _symmetry_space_group_name_H-M 'P -1' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 9.0278(7) _cell_length_b 10.5146(9) _cell_length_c 13.4184(11) _cell_angle_alpha 79.220(1) _cell_angle_beta 75.225(1) _cell_angle_gamma 72.025(1) _cell_volume 1163.34(16) _cell_formula_units_Z 2 _cell_measurement_temperature 298 _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description plate _exptl_crystal_colour colorless _exptl_crystal_size_max 0.41 _exptl_crystal_size_mid 0.22 _exptl_crystal_size_min 0.18 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.394 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 504 _exptl_absorpt_coefficient_mu 0.311 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.8832 _exptl_absorpt_correction_T_max 0.9462 _exptl_absorpt_process_details 'SADABS-Bruker Nonius area detector scaling and absorption correction - V2.10' _exptl_special_details ; ; _diffrn_ambient_temperature 298 _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'CCD area detector' _diffrn_measurement_method 'phi and omega scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 11260 _diffrn_reflns_av_R_equivalents 0.0353 _diffrn_reflns_av_sigmaI/netI 0.0364 _diffrn_reflns_limit_h_min -10 _diffrn_reflns_limit_h_max 10 _diffrn_reflns_limit_k_min -12 _diffrn_reflns_limit_k_max 12 _diffrn_reflns_limit_l_min -15 _diffrn_reflns_limit_l_max 15 _diffrn_reflns_theta_min 1.58 _diffrn_reflns_theta_max 25.00 _reflns_number_total 4080 _reflns_number_gt 3093 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'Bruker SMART' _computing_data_reduction 'Bruker SAINT' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Ortep-3 for Windows/Platon' _computing_publication_material 'Bruker SHELXTL' _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^)+(0.0587P)^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 none _refine_ls_extinction_coef ? _refine_ls_number_reflns 4080 _refine_ls_number_parameters 311 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0557 _refine_ls_R_factor_gt 0.0412 _refine_ls_wR_factor_ref 0.1064 _refine_ls_wR_factor_gt 0.1006 _refine_ls_goodness_of_fit_ref 0.997 _refine_ls_restrained_S_all 0.997 _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 Cl1 Cl 0.26803(7) 0.48473(6) 0.41912(5) 0.0687(2) Uani 1 1 d . . . Cl2 Cl 0.59546(9) 0.14210(7) 0.46767(5) 0.0832(2) Uani 1 1 d . . . O1 O 0.57179(19) -0.20808(14) 0.27794(12) 0.0674(5) Uani 1 1 d . . . O2 O 0.02771(16) 0.51071(11) 0.12057(10) 0.0469(3) Uani 1 1 d . . . O3 O 0.22964(17) 0.14028(13) -0.04205(10) 0.0553(4) Uani 1 1 d . . . N1 N 0.11859(19) 0.31781(15) 0.04740(12) 0.0402(4) Uani 1 1 d . . . H1N H 0.093(2) 0.3625(17) -0.0045(14) 0.036(5) Uiso 1 1 d . . . C1 C 0.2560(2) -0.04509(17) 0.14024(13) 0.0357(4) Uani 1 1 d . . . C2 C 0.1390(2) -0.07946(19) 0.10894(15) 0.0463(5) Uani 1 1 d . . . H2 H 0.0575 -0.0120 0.0846 0.056 Uiso 1 1 calc R . . C3 C 0.1427(3) -0.2125(2) 0.11372(16) 0.0565(6) Uani 1 1 d . . . H3 H 0.0643 -0.2341 0.0921 0.068 Uiso 1 1 calc R . . C4 C 0.2614(3) -0.3131(2) 0.15019(17) 0.0588(6) Uani 1 1 d . . . H4 H 0.2655 -0.4028 0.1512 0.071 Uiso 1 1 calc R . . C5 C 0.3734(3) -0.28134(18) 0.18505(16) 0.0525(5) Uani 1 1 d . . . H5 H 0.4517 -0.3498 0.2117 0.063 Uiso 1 1 calc R . . C6 C 0.3720(2) -0.14741(17) 0.18123(14) 0.0385(4) Uani 1 1 d . . . C7 C 0.4897(2) -0.11841(18) 0.22748(14) 0.0434(5) Uani 1 1 d . . . C8 C 0.5010(2) 0.02241(17) 0.21088(14) 0.0386(4) Uani 1 1 d . . . C9 C 0.4187(2) 0.11604(17) 0.13001(14) 0.0377(4) Uani 1 1 d . . . H9A H 0.4832 0.0977 0.0617 0.045 Uiso 1 1 calc R . . H9B H 0.4097 0.2081 0.1380 0.045 Uiso 1 1 calc R . . C10 C 0.2504(2) 0.10169(16) 0.13743(13) 0.0337(4) Uani 1 1 d . . . C11 C 0.1338(2) 0.15729(16) 0.23507(13) 0.0346(4) Uani 1 1 d . . . H11A H 0.0337 0.1367 0.2422 0.042 Uiso 1 1 calc R . . H11B H 0.1771 0.1124 0.2956 0.042 Uiso 1 1 calc R . . C12 C 0.1026(2) 0.30648(16) 0.23191(13) 0.0329(4) Uani 1 1 d . . . C13 C 0.0802(2) 0.38809(17) 0.13185(13) 0.0356(4) Uani 1 1 d . . . C14 C 0.1986(2) 0.18396(17) 0.03995(14) 0.0374(4) Uani 1 1 d . . . C15 C 0.0904(2) 0.37192(17) 0.31130(13) 0.0381(4) Uani 1 1 d . . . H15 H 0.0772 0.4643 0.2964 0.046 Uiso 1 1 calc R . . C16 C 0.0955(2) 0.31478(18) 0.41893(13) 0.0407(5) Uani 1 1 d . . . C17 C 0.1713(2) 0.3616(2) 0.47700(15) 0.0495(5) Uani 1 1 d . . . C18 C 0.1737(3) 0.3121(3) 0.57888(19) 0.0724(8) Uani 1 1 d . . . H18 H 0.2275 0.3437 0.6152 0.087 Uiso 1 1 calc R . . C19 C 0.0969(4) 0.2165(3) 0.62691(19) 0.0849(9) Uani 1 1 d . . . H19 H 0.0986 0.1829 0.6960 0.102 Uiso 1 1 calc R . . C20 C 0.0169(3) 0.1697(2) 0.57310(19) 0.0771(8) Uani 1 1 d . . . H20 H -0.0371 0.1060 0.6063 0.093 Uiso 1 1 calc R . . C21 C 0.0171(3) 0.2174(2) 0.46996(15) 0.0545(5) Uani 1 1 d . . . H21 H -0.0356 0.1843 0.4339 0.065 Uiso 1 1 calc R . . C22 C 0.5850(2) 0.05347(19) 0.26719(15) 0.0452(5) Uani 1 1 d . . . H22 H 0.6223 -0.0137 0.3179 0.054 Uiso 1 1 calc R . . C23 C 0.6257(2) 0.18021(19) 0.25890(16) 0.0474(5) Uani 1 1 d . . . C24 C 0.6357(2) 0.2296(2) 0.34567(17) 0.0537(5) Uani 1 1 d . . . C25 C 0.6726(2) 0.3496(2) 0.3383(2) 0.0672(7) Uani 1 1 d . . . H25 H 0.6755 0.3815 0.3977 0.081 Uiso 1 1 calc R . . C26 C 0.7050(3) 0.4211(2) 0.2432(2) 0.0715(7) Uani 1 1 d . . . H26 H 0.7290 0.5023 0.2380 0.086 Uiso 1 1 calc R . . C27 C 0.7024(3) 0.3739(2) 0.1559(2) 0.0719(7) Uani 1 1 d . . . H27 H 0.7265 0.4224 0.0913 0.086 Uiso 1 1 calc R . . C28 C 0.6641(2) 0.2548(2) 0.16264(18) 0.0596(6) Uani 1 1 d . . . H28 H 0.6639 0.2234 0.1023 0.072 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 Cl1 0.0596(4) 0.0799(4) 0.0772(4) -0.0295(3) -0.0237(3) -0.0146(3) Cl2 0.0958(5) 0.1080(5) 0.0586(4) -0.0205(4) -0.0205(3) -0.0365(4) O1 0.0806(11) 0.0479(9) 0.0835(11) 0.0109(8) -0.0540(9) -0.0129(8) O2 0.0727(9) 0.0287(7) 0.0458(8) 0.0030(6) -0.0288(7) -0.0140(6) O3 0.0748(10) 0.0536(8) 0.0326(8) -0.0093(6) -0.0170(7) -0.0035(7) N1 0.0558(10) 0.0358(9) 0.0302(9) 0.0032(7) -0.0219(8) -0.0084(7) C1 0.0419(10) 0.0354(10) 0.0312(10) -0.0051(8) -0.0100(8) -0.0102(8) C2 0.0512(12) 0.0448(11) 0.0493(12) -0.0045(9) -0.0215(10) -0.0140(9) C3 0.0697(15) 0.0573(13) 0.0574(14) -0.0066(11) -0.0253(11) -0.0291(12) C4 0.0797(16) 0.0412(12) 0.0663(15) -0.0072(10) -0.0245(13) -0.0239(11) C5 0.0627(13) 0.0339(11) 0.0596(14) 0.0003(9) -0.0219(11) -0.0077(10) C6 0.0442(11) 0.0359(10) 0.0354(10) -0.0035(8) -0.0115(8) -0.0091(8) C7 0.0462(11) 0.0427(11) 0.0408(11) -0.0008(9) -0.0173(9) -0.0071(9) C8 0.0354(10) 0.0424(11) 0.0385(10) -0.0066(8) -0.0120(8) -0.0068(8) C9 0.0395(10) 0.0367(10) 0.0373(10) -0.0050(8) -0.0083(8) -0.0104(8) C10 0.0378(10) 0.0322(9) 0.0311(10) -0.0010(7) -0.0109(8) -0.0081(8) C11 0.0393(10) 0.0322(9) 0.0325(10) 0.0000(7) -0.0103(8) -0.0100(8) C12 0.0330(9) 0.0322(9) 0.0339(10) -0.0009(8) -0.0112(8) -0.0080(7) C13 0.0407(10) 0.0336(10) 0.0382(11) -0.0003(8) -0.0174(8) -0.0131(8) C14 0.0389(10) 0.0390(10) 0.0344(11) -0.0023(8) -0.0112(8) -0.0094(8) C15 0.0413(10) 0.0341(10) 0.0385(11) -0.0017(8) -0.0134(8) -0.0073(8) C16 0.0426(11) 0.0401(10) 0.0315(10) -0.0087(8) -0.0085(8) 0.0032(9) C17 0.0442(11) 0.0557(12) 0.0408(12) -0.0169(10) -0.0152(9) 0.0087(10) C18 0.0634(16) 0.0937(19) 0.0444(14) -0.0231(13) -0.0263(12) 0.0218(14) C19 0.088(2) 0.095(2) 0.0345(14) -0.0045(14) -0.0149(14) 0.0267(17) C20 0.0813(18) 0.0625(16) 0.0493(15) 0.0114(12) 0.0095(13) 0.0052(13) C21 0.0621(14) 0.0498(12) 0.0400(12) -0.0030(10) -0.0039(10) -0.0055(10) C22 0.0430(11) 0.0471(11) 0.0473(12) -0.0062(9) -0.0167(9) -0.0090(9) C23 0.0341(10) 0.0512(12) 0.0598(14) -0.0121(10) -0.0169(9) -0.0070(9) C24 0.0392(11) 0.0626(13) 0.0655(15) -0.0213(11) -0.0166(10) -0.0099(10) C25 0.0424(13) 0.0716(16) 0.098(2) -0.0382(15) -0.0178(13) -0.0109(12) C26 0.0441(13) 0.0612(15) 0.117(2) -0.0225(16) -0.0196(14) -0.0160(11) C27 0.0519(14) 0.0718(16) 0.098(2) 0.0035(15) -0.0207(13) -0.0295(12) C28 0.0503(13) 0.0701(15) 0.0663(15) -0.0041(12) -0.0184(11) -0.0251(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 Cl1 C17 1.738(2) . ? Cl2 C24 1.731(2) . ? O1 C7 1.218(2) . ? O2 C13 1.2232(19) . ? O3 C14 1.205(2) . ? N1 C14 1.379(2) . ? N1 C13 1.380(2) . ? N1 H1N 0.808(17) . ? C1 C6 1.390(2) . ? C1 C2 1.394(2) . ? C1 C10 1.522(2) . ? C2 C3 1.378(3) . ? C2 H2 0.9300 . ? C3 C4 1.372(3) . ? C3 H3 0.9300 . ? C4 C5 1.365(3) . ? C4 H4 0.9300 . ? C5 C6 1.396(2) . ? C5 H5 0.9300 . ? C6 C7 1.488(2) . ? C7 C8 1.487(2) . ? C8 C22 1.338(2) . ? C8 C9 1.503(2) . ? C9 C10 1.549(2) . ? C9 H9A 0.9700 . ? C9 H9B 0.9700 . ? C10 C14 1.522(2) . ? C10 C11 1.539(2) . ? C11 C12 1.500(2) . ? C11 H11A 0.9700 . ? C11 H11B 0.9700 . ? C12 C15 1.337(2) . ? C12 C13 1.477(2) . ? C15 C16 1.463(2) . ? C15 H15 0.9300 . ? C16 C17 1.393(3) . ? C16 C21 1.398(3) . ? C17 C18 1.372(3) . ? C18 C19 1.366(4) . ? C18 H18 0.9300 . ? C19 C20 1.379(4) . ? C19 H19 0.9300 . ? C20 C21 1.381(3) . ? C20 H20 0.9300 . ? C21 H21 0.9300 . ? C22 C23 1.466(3) . ? C22 H22 0.9300 . ? C23 C24 1.394(3) . ? C23 C28 1.401(3) . ? C24 C25 1.382(3) . ? C25 C26 1.366(3) . ? C25 H25 0.9300 . ? C26 C27 1.363(3) . ? C26 H26 0.9300 . ? C27 C28 1.381(3) . ? C27 H27 0.9300 . ? C28 H28 0.9300 . ? 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 N1 C13 128.45(15) . . ? C14 N1 H1N 116.8(13) . . ? C13 N1 H1N 114.8(13) . . ? C6 C1 C2 118.60(16) . . ? C6 C1 C10 120.37(15) . . ? C2 C1 C10 120.88(15) . . ? C3 C2 C1 120.68(18) . . ? C3 C2 H2 119.7 . . ? C1 C2 H2 119.7 . . ? C4 C3 C2 120.35(19) . . ? C4 C3 H3 119.8 . . ? C2 C3 H3 119.8 . . ? C5 C4 C3 119.82(19) . . ? C5 C4 H4 120.1 . . ? C3 C4 H4 120.1 . . ? C4 C5 C6 120.89(18) . . ? C4 C5 H5 119.6 . . ? C6 C5 H5 119.6 . . ? C1 C6 C5 119.55(17) . . ? C1 C6 C7 121.88(15) . . ? C5 C6 C7 118.46(16) . . ? O1 C7 C8 122.03(17) . . ? O1 C7 C6 120.17(17) . . ? C8 C7 C6 117.79(15) . . ? C22 C8 C7 117.60(16) . . ? C22 C8 C9 126.16(17) . . ? C7 C8 C9 116.23(15) . . ? C8 C9 C10 112.63(14) . . ? C8 C9 H9A 109.1 . . ? C10 C9 H9A 109.1 . . ? C8 C9 H9B 109.1 . . ? C10 C9 H9B 109.1 . . ? H9A C9 H9B 107.8 . . ? C1 C10 C14 110.46(14) . . ? C1 C10 C11 109.01(14) . . ? C14 C10 C11 110.41(14) . . ? C1 C10 C9 110.80(14) . . ? C14 C10 C9 105.10(14) . . ? C11 C10 C9 111.04(14) . . ? C12 C11 C10 112.79(14) . . ? C12 C11 H11A 109.0 . . ? C10 C11 H11A 109.0 . . ? C12 C11 H11B 109.0 . . ? C10 C11 H11B 109.0 . . ? H11A C11 H11B 107.8 . . ? C15 C12 C13 117.41(15) . . ? C15 C12 C11 126.17(15) . . ? C13 C12 C11 116.41(14) . . ? O2 C13 N1 119.39(15) . . ? O2 C13 C12 124.43(16) . . ? N1 C13 C12 116.16(15) . . ? O3 C14 N1 119.70(16) . . ? O3 C14 C10 123.93(16) . . ? N1 C14 C10 116.28(15) . . ? C12 C15 C16 127.40(16) . . ? C12 C15 H15 116.3 . . ? C16 C15 H15 116.3 . . ? C17 C16 C21 117.01(18) . . ? C17 C16 C15 120.94(18) . . ? C21 C16 C15 121.94(17) . . ? C18 C17 C16 121.9(2) . . ? C18 C17 Cl1 118.59(19) . . ? C16 C17 Cl1 119.47(15) . . ? C19 C18 C17 119.9(3) . . ? C19 C18 H18 120.0 . . ? C17 C18 H18 120.0 . . ? C18 C19 C20 120.1(2) . . ? C18 C19 H19 120.0 . . ? C20 C19 H19 120.0 . . ? C19 C20 C21 120.0(3) . . ? C19 C20 H20 120.0 . . ? C21 C20 H20 120.0 . . ? C20 C21 C16 121.0(2) . . ? C20 C21 H21 119.5 . . ? C16 C21 H21 119.5 . . ? C8 C22 C23 128.05(18) . . ? C8 C22 H22 116.0 . . ? C23 C22 H22 116.0 . . ? C24 C23 C28 116.44(19) . . ? C24 C23 C22 121.82(19) . . ? C28 C23 C22 121.67(19) . . ? C25 C24 C23 122.0(2) . . ? C25 C24 Cl2 118.14(18) . . ? C23 C24 Cl2 119.85(16) . . ? C26 C25 C24 119.6(2) . . ? C26 C25 H25 120.2 . . ? C24 C25 H25 120.2 . . ? C27 C26 C25 120.3(2) . . ? C27 C26 H26 119.8 . . ? C25 C26 H26 119.8 . . ? C26 C27 C28 120.5(3) . . ? C26 C27 H27 119.8 . . ? C28 C27 H27 119.8 . . ? C27 C28 C23 121.1(2) . . ? C27 C28 H28 119.4 . . ? C23 C28 H28 119.4 . . ? _diffrn_measured_fraction_theta_max 0.997 _diffrn_reflns_theta_full 25.00 _diffrn_measured_fraction_theta_full 0.997 _refine_diff_density_max 0.241 _refine_diff_density_min -0.260 _refine_diff_density_rms 0.039 ###END### data_4d _database_code_depnum_ccdc_archive 'CCDC 656197' _audit_creation_method SHELXL-97 _chemical_name_systematic ; 3,3-Spiro-bis[{5-(E)-4-ethylbenzylidene}piperidine-2,6-dione] ; _chemical_name_common 3,3-Spiro-bis((5-(E)-4-ethylbenzylidene)piperidine-2,6-dione) _chemical_melting_point 218(2) _chemical_formula_moiety 'C27 H26 N2 O4' _chemical_formula_sum 'C27 H26 N2 O4' _chemical_formula_weight 442.50 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 0.0000 '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 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Triclinic _symmetry_space_group_name_H-M 'P -1 ' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 10.0689(7) _cell_length_b 10.7855(8) _cell_length_c 12.4469(9) _cell_angle_alpha 101.142(1) _cell_angle_beta 108.914(1) _cell_angle_gamma 105.628(1) _cell_volume 1171.60(15) _cell_formula_units_Z 2 _cell_measurement_temperature 298 _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description rectangular _exptl_crystal_colour colorless _exptl_crystal_size_max 0.40 _exptl_crystal_size_mid 0.32 _exptl_crystal_size_min 0.26 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.254 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 468 _exptl_absorpt_coefficient_mu 0.085 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.9669 _exptl_absorpt_correction_T_max 0.9783 _exptl_absorpt_process_details 'SADABS-Bruker Nonius area detector scaling and absorption correction - V2.10' _exptl_special_details ; ? ; _diffrn_ambient_temperature 298 _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'CCD area detector' _diffrn_measurement_method 'phi and omega scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 11347 _diffrn_reflns_av_R_equivalents 0.0266 _diffrn_reflns_av_sigmaI/netI 0.0291 _diffrn_reflns_limit_h_min -11 _diffrn_reflns_limit_h_max 11 _diffrn_reflns_limit_k_min -12 _diffrn_reflns_limit_k_max 12 _diffrn_reflns_limit_l_min -14 _diffrn_reflns_limit_l_max 14 _diffrn_reflns_theta_min 1.82 _diffrn_reflns_theta_max 25.00 _reflns_number_total 4099 _reflns_number_gt 2930 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'Bruker SMART' _computing_data_reduction 'Bruker SAINT' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Ortep-3 for Windows/Platon' _computing_publication_material 'Bruker SHELXTL' _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^)+(0.1150P)^2^+0.1351P] 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 none _refine_ls_extinction_coef ? _refine_ls_number_reflns 4099 _refine_ls_number_parameters 308 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0803 _refine_ls_R_factor_gt 0.0617 _refine_ls_wR_factor_ref 0.1963 _refine_ls_wR_factor_gt 0.1824 _refine_ls_goodness_of_fit_ref 1.070 _refine_ls_restrained_S_all 1.070 _refine_ls_shift/su_max 0.001 _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 O3 O 0.40557(18) 0.14994(16) 0.82589(15) 0.0598(5) Uani 1 1 d . . . O2 O 0.6133(2) 0.15188(18) 1.10355(15) 0.0635(5) Uani 1 1 d . . . N1 N 0.7251(2) 0.0159(2) 1.0394(2) 0.0556(6) Uani 1 1 d . . . N2 N 0.5587(2) 0.3534(2) 0.95587(19) 0.0584(6) Uani 1 1 d . . . O4 O 0.6906(2) 0.55326(19) 1.09904(19) 0.0841(7) Uani 1 1 d . . . C18 C 0.5307(3) 0.2224(2) 0.8984(2) 0.0489(6) Uani 1 1 d . . . C12 C 0.6406(3) 0.0632(2) 0.8200(2) 0.0504(6) Uani 1 1 d . . . H12A H 0.5408 -0.0051 0.7887 0.061 Uiso 1 1 calc R . . H12B H 0.6496 0.1036 0.7583 0.061 Uiso 1 1 calc R . . O1 O 0.8314(2) -0.12894(19) 0.98266(18) 0.0805(6) Uani 1 1 d . . . C11 C 0.7742(3) -0.0462(2) 0.9598(2) 0.0573(6) Uani 1 1 d . . . C14 C 0.6615(2) 0.1135(2) 1.0316(2) 0.0500(6) Uani 1 1 d . . . C13 C 0.6615(2) 0.1726(2) 0.92986(19) 0.0452(5) Uani 1 1 d . . . C16 C 0.8278(3) 0.4108(2) 1.0662(2) 0.0488(6) Uani 1 1 d . . . C19 C 0.9507(3) 0.4957(2) 1.1612(2) 0.0540(6) Uani 1 1 d . . . H19 H 0.9329 0.5635 1.2067 0.065 Uiso 1 1 calc R . . C10 C 0.7559(3) -0.0017(2) 0.8520(2) 0.0530(6) Uani 1 1 d . . . C15 C 0.8132(3) 0.2901(2) 0.9745(2) 0.0509(6) Uani 1 1 d . . . H15A H 0.8941 0.2583 1.0082 0.061 Uiso 1 1 calc R . . H15B H 0.8244 0.3170 0.9069 0.061 Uiso 1 1 calc R . . C17 C 0.6919(3) 0.4469(2) 1.0453(2) 0.0589(7) Uani 1 1 d . . . C9 C 0.8488(3) -0.0136(3) 0.7982(2) 0.0629(7) Uani 1 1 d . . . H9 H 0.9170 -0.0538 0.8297 0.075 Uiso 1 1 calc R . . C20 C 1.1067(3) 0.5040(2) 1.2082(2) 0.0536(6) Uani 1 1 d . . . C6 C 0.8551(3) 0.0299(3) 0.6946(2) 0.0598(7) Uani 1 1 d . . . C5 C 0.9906(3) 0.1108(3) 0.6999(3) 0.0702(8) Uani 1 1 d . . . H5 H 1.0772 0.1372 0.7689 0.084 Uiso 1 1 calc R . . C25 C 1.2071(3) 0.6151(3) 1.3055(2) 0.0697(8) Uani 1 1 d . . . H25 H 1.1715 0.6761 1.3401 0.084 Uiso 1 1 calc R . . C7 C 0.7298(3) -0.0072(3) 0.5897(2) 0.0724(8) Uani 1 1 d . . . H7 H 0.6370 -0.0615 0.5838 0.087 Uiso 1 1 calc R . . C8 C 0.7396(4) 0.0345(3) 0.4940(3) 0.0820(9) Uani 1 1 d . . . H8 H 0.6534 0.0071 0.4245 0.098 Uiso 1 1 calc R . . C21 C 1.1683(3) 0.4189(3) 1.1591(3) 0.0848(10) Uani 1 1 d . . . H21 H 1.1061 0.3456 1.0911 0.102 Uiso 1 1 calc R . . C3 C 0.8739(4) 0.1159(3) 0.4989(3) 0.0775(8) Uani 1 1 d . . . C4 C 0.9987(4) 0.1530(3) 0.6034(3) 0.0808(9) Uani 1 1 d . . . H4 H 1.0910 0.2081 0.6092 0.097 Uiso 1 1 calc R . . C22 C 1.3192(3) 0.4413(3) 1.2091(3) 0.0969(11) Uani 1 1 d . . . H22 H 1.3556 0.3799 1.1760 0.116 Uiso 1 1 calc R . . C24 C 1.3583(3) 0.6371(4) 1.3520(3) 0.0904(10) Uani 1 1 d . . . H24 H 1.4225 0.7133 1.4169 0.108 Uiso 1 1 calc R . . C23 C 1.4175(3) 0.5498(4) 1.3055(3) 0.0894(10) Uani 1 1 d . . . C26 C 1.5830(4) 0.5779(6) 1.3544(5) 0.151(2) Uani 1 1 d . . . H26A H 1.6244 0.6245 1.3067 0.181 Uiso 1 1 calc R . . H26B H 1.6265 0.6403 1.4346 0.181 Uiso 1 1 calc R . . C2 C 0.8827(6) 0.1617(4) 0.3942(3) 0.1143(13) Uani 1 1 d . . . H2A H 0.9583 0.1355 0.3735 0.137 Uiso 1 1 calc R . . H2B H 0.7870 0.1126 0.3268 0.137 Uiso 1 1 calc R . . C1 C 0.9149(12) 0.2942(6) 0.4077(5) 0.281(5) Uani 1 1 d . . . H1A H 0.8248 0.3146 0.3936 0.422 Uiso 1 1 calc R . . H1B H 0.9563 0.3175 0.3518 0.422 Uiso 1 1 calc R . . H1C H 0.9867 0.3455 0.4875 0.422 Uiso 1 1 calc R . . C27 C 1.6308(7) 0.4726(9) 1.3595(9) 0.278(5) Uani 1 1 d . . . H27A H 1.6965 0.4872 1.4401 0.416 Uiso 1 1 calc R . . H27B H 1.6842 0.4652 1.3085 0.416 Uiso 1 1 calc R . . H27C H 1.5458 0.3905 1.3335 0.416 Uiso 1 1 calc R . . H1N H 0.720(3) -0.021(3) 1.090(2) 0.055(8) Uiso 1 1 d . . . H2N H 0.477(3) 0.386(3) 0.943(2) 0.069(7) 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 O3 0.0455(10) 0.0548(10) 0.0643(11) 0.0153(8) 0.0081(8) 0.0148(8) O2 0.0680(11) 0.0698(11) 0.0569(11) 0.0217(9) 0.0278(9) 0.0261(9) N1 0.0553(13) 0.0550(12) 0.0564(13) 0.0256(11) 0.0152(10) 0.0221(10) N2 0.0476(12) 0.0508(12) 0.0667(13) 0.0068(10) 0.0121(10) 0.0233(10) O4 0.0649(12) 0.0638(12) 0.0965(15) -0.0109(11) 0.0086(10) 0.0358(10) C18 0.0473(14) 0.0484(13) 0.0491(13) 0.0170(11) 0.0166(11) 0.0159(11) C12 0.0511(13) 0.0453(12) 0.0471(13) 0.0103(10) 0.0120(11) 0.0175(11) O1 0.0927(15) 0.0653(12) 0.0821(14) 0.0253(10) 0.0180(11) 0.0450(11) C11 0.0529(14) 0.0432(13) 0.0615(15) 0.0106(12) 0.0082(12) 0.0175(11) C14 0.0404(12) 0.0466(13) 0.0476(13) 0.0093(10) 0.0087(11) 0.0069(10) C13 0.0435(12) 0.0408(12) 0.0455(12) 0.0111(10) 0.0130(10) 0.0138(10) C16 0.0477(13) 0.0389(12) 0.0569(14) 0.0136(11) 0.0178(11) 0.0157(10) C19 0.0542(14) 0.0426(12) 0.0601(15) 0.0109(11) 0.0185(12) 0.0182(11) C10 0.0531(14) 0.0400(12) 0.0517(14) 0.0027(10) 0.0098(11) 0.0169(11) C15 0.0473(13) 0.0445(12) 0.0568(14) 0.0116(11) 0.0195(11) 0.0144(10) C17 0.0513(15) 0.0492(14) 0.0687(16) 0.0101(12) 0.0161(13) 0.0219(12) C9 0.0602(16) 0.0583(15) 0.0623(16) 0.0083(12) 0.0140(13) 0.0294(13) C20 0.0497(14) 0.0443(13) 0.0585(14) 0.0124(11) 0.0149(11) 0.0150(11) C6 0.0581(16) 0.0577(15) 0.0577(15) 0.0030(12) 0.0185(13) 0.0276(13) C5 0.0583(17) 0.0745(18) 0.0741(19) 0.0149(15) 0.0206(14) 0.0310(14) C25 0.0610(17) 0.0681(17) 0.0606(16) 0.0017(14) 0.0125(13) 0.0207(14) C7 0.0627(17) 0.0766(19) 0.0544(16) -0.0014(14) 0.0165(14) 0.0133(14) C8 0.079(2) 0.087(2) 0.0533(17) -0.0041(15) 0.0146(15) 0.0224(18) C21 0.0561(17) 0.0631(17) 0.102(2) -0.0085(16) 0.0101(16) 0.0212(14) C3 0.094(2) 0.0698(18) 0.0628(18) 0.0057(15) 0.0331(18) 0.0287(17) C4 0.071(2) 0.077(2) 0.096(2) 0.0161(18) 0.0422(19) 0.0257(16) C22 0.0594(19) 0.086(2) 0.118(3) -0.005(2) 0.0168(19) 0.0324(17) C24 0.0587(18) 0.094(2) 0.076(2) -0.0088(17) 0.0040(15) 0.0173(17) C23 0.0553(17) 0.104(3) 0.082(2) 0.0090(19) 0.0085(16) 0.0268(18) C26 0.064(2) 0.189(5) 0.151(4) 0.002(4) 0.005(2) 0.055(3) C2 0.162(4) 0.097(3) 0.083(2) 0.023(2) 0.057(3) 0.038(3) C1 0.494(15) 0.139(5) 0.114(4) 0.070(4) 0.050(6) 0.031(7) C27 0.112(5) 0.357(12) 0.398(13) 0.210(11) 0.056(6) 0.124(7) _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 O3 C18 1.213(3) . ? O2 C14 1.206(3) . ? N1 C14 1.375(3) . ? N1 C11 1.383(3) . ? N1 H1N 0.81(2) . ? N2 C18 1.360(3) . ? N2 C17 1.387(3) . ? N2 H2N 0.96(3) . ? O4 C17 1.217(3) . ? C18 C13 1.519(3) . ? C12 C10 1.497(3) . ? C12 C13 1.537(3) . ? C12 H12A 0.9700 . ? C12 H12B 0.9700 . ? O1 C11 1.216(3) . ? C11 C10 1.484(3) . ? C14 C13 1.524(3) . ? C13 C15 1.543(3) . ? C16 C19 1.338(3) . ? C16 C17 1.479(3) . ? C16 C15 1.495(3) . ? C19 C20 1.458(3) . ? C19 H19 0.9300 . ? C10 C9 1.333(3) . ? C15 H15A 0.9700 . ? C15 H15B 0.9700 . ? C9 C6 1.469(4) . ? C9 H9 0.9300 . ? C20 C25 1.385(4) . ? C20 C21 1.391(4) . ? C6 C5 1.381(4) . ? C6 C7 1.384(4) . ? C5 C4 1.382(4) . ? C5 H5 0.9300 . ? C25 C24 1.375(4) . ? C25 H25 0.9300 . ? C7 C8 1.374(4) . ? C7 H7 0.9300 . ? C8 C3 1.375(4) . ? C8 H8 0.9300 . ? C21 C22 1.373(4) . ? C21 H21 0.9300 . ? C3 C4 1.378(4) . ? C3 C2 1.500(5) . ? C4 H4 0.9300 . ? C22 C23 1.361(4) . ? C22 H22 0.9300 . ? C24 C23 1.376(4) . ? C24 H24 0.9300 . ? C23 C26 1.496(5) . ? C26 C27 1.352(8) . ? C26 H26A 0.9700 . ? C26 H26B 0.9700 . ? C2 C1 1.342(6) . ? C2 H2A 0.9700 . ? C2 H2B 0.9700 . ? C1 H1A 0.9600 . ? C1 H1B 0.9600 . ? C1 H1C 0.9600 . ? C27 H27A 0.9600 . ? C27 H27B 0.9600 . ? C27 H27C 0.9600 . ? 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 N1 C11 128.5(2) . . ? C14 N1 H1N 117.0(18) . . ? C11 N1 H1N 113.4(18) . . ? C18 N2 C17 127.8(2) . . ? C18 N2 H2N 119.3(16) . . ? C17 N2 H2N 112.4(16) . . ? O3 C18 N2 120.5(2) . . ? O3 C18 C13 122.4(2) . . ? N2 C18 C13 117.1(2) . . ? C10 C12 C13 110.72(18) . . ? C10 C12 H12A 109.5 . . ? C13 C12 H12A 109.5 . . ? C10 C12 H12B 109.5 . . ? C13 C12 H12B 109.5 . . ? H12A C12 H12B 108.1 . . ? O1 C11 N1 119.6(2) . . ? O1 C11 C10 124.6(2) . . ? N1 C11 C10 115.8(2) . . ? O2 C14 N1 121.4(2) . . ? O2 C14 C13 122.8(2) . . ? N1 C14 C13 115.7(2) . . ? C18 C13 C14 107.68(18) . . ? C18 C13 C12 109.19(18) . . ? C14 C13 C12 110.19(18) . . ? C18 C13 C15 111.31(18) . . ? C14 C13 C15 107.61(18) . . ? C12 C13 C15 110.80(18) . . ? C19 C16 C17 115.5(2) . . ? C19 C16 C15 128.3(2) . . ? C17 C16 C15 116.1(2) . . ? C16 C19 C20 133.4(2) . . ? C16 C19 H19 113.3 . . ? C20 C19 H19 113.3 . . ? C9 C10 C11 118.1(2) . . ? C9 C10 C12 126.1(2) . . ? C11 C10 C12 115.6(2) . . ? C16 C15 C13 113.22(18) . . ? C16 C15 H15A 108.9 . . ? C13 C15 H15A 108.9 . . ? C16 C15 H15B 108.9 . . ? C13 C15 H15B 108.9 . . ? H15A C15 H15B 107.7 . . ? O4 C17 N2 118.7(2) . . ? O4 C17 C16 124.4(2) . . ? N2 C17 C16 116.9(2) . . ? C10 C9 C6 127.1(2) . . ? C10 C9 H9 116.5 . . ? C6 C9 H9 116.5 . . ? C25 C20 C21 116.2(2) . . ? C25 C20 C19 116.7(2) . . ? C21 C20 C19 126.8(2) . . ? C5 C6 C7 117.5(3) . . ? C5 C6 C9 119.7(2) . . ? C7 C6 C9 122.8(3) . . ? C6 C5 C4 120.5(3) . . ? C6 C5 H5 119.7 . . ? C4 C5 H5 119.7 . . ? C24 C25 C20 121.4(3) . . ? C24 C25 H25 119.3 . . ? C20 C25 H25 119.3 . . ? C8 C7 C6 121.4(3) . . ? C8 C7 H7 119.3 . . ? C6 C7 H7 119.3 . . ? C7 C8 C3 121.4(3) . . ? C7 C8 H8 119.3 . . ? C3 C8 H8 119.3 . . ? C22 C21 C20 121.2(3) . . ? C22 C21 H21 119.4 . . ? C20 C21 H21 119.4 . . ? C8 C3 C4 117.2(3) . . ? C8 C3 C2 120.9(3) . . ? C4 C3 C2 121.9(3) . . ? C3 C4 C5 121.9(3) . . ? C3 C4 H4 119.0 . . ? C5 C4 H4 119.0 . . ? C23 C22 C21 122.4(3) . . ? C23 C22 H22 118.8 . . ? C21 C22 H22 118.8 . . ? C25 C24 C23 122.0(3) . . ? C25 C24 H24 119.0 . . ? C23 C24 H24 119.0 . . ? C22 C23 C24 116.7(3) . . ? C22 C23 C26 121.9(3) . . ? C24 C23 C26 121.3(3) . . ? C27 C26 C23 118.6(5) . . ? C27 C26 H26A 107.7 . . ? C23 C26 H26A 107.7 . . ? C27 C26 H26B 107.7 . . ? C23 C26 H26B 107.7 . . ? H26A C26 H26B 107.1 . . ? C1 C2 C3 117.0(4) . . ? C1 C2 H2A 108.0 . . ? C3 C2 H2A 108.0 . . ? C1 C2 H2B 108.0 . . ? C3 C2 H2B 108.0 . . ? H2A C2 H2B 107.3 . . ? C2 C1 H1A 109.5 . . ? C2 C1 H1B 109.5 . . ? H1A C1 H1B 109.5 . . ? C2 C1 H1C 109.5 . . ? H1A C1 H1C 109.5 . . ? H1B C1 H1C 109.5 . . ? C26 C27 H27A 109.5 . . ? C26 C27 H27B 109.5 . . ? H27A C27 H27B 109.5 . . ? C26 C27 H27C 109.5 . . ? H27A C27 H27C 109.5 . . ? H27B C27 H27C 109.5 . . ? _diffrn_measured_fraction_theta_max 0.998 _diffrn_reflns_theta_full 25.00 _diffrn_measured_fraction_theta_full 0.998 _refine_diff_density_max 0.448 _refine_diff_density_min -0.310 _refine_diff_density_rms 0.046 ###END###