Supplementary Material (ESI) for Perkin Transactions This journal is © The Royal Society of Chemistry 2001 data_global _journal_coden_Cambridge 207 _publ_requested_journal 'Perkin Transactions 1' loop_ _publ_author_name 'Aburel, Pompiliu S.' 'Ma, Kuangbiao' 'Romming, Christian' 'Undheim, K.' _publ_contact_author_name Prof K Undheim'' _publ_contact_author_address ; Prof K Undheim Department of Chemistry University of Oslo Pb 1033 Blinder Oslo N-0315 NORWAY ; _publ_contact_author_email 'KJELL.UNDHEIM@KJEMI.UIO.NO' data_42 _database_code_CSD 161066 _audit_creation_method SHELXL-97 _chemical_name_systematic ; cis-7,7-ethylenedioxospiro[4,5]decan-3-en-1-yl p-nitrobenzoate ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C19 H21 N O6' _chemical_formula_weight 359.37 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 ? _symmetry_space_group_name_H-M P2(1)/c loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y-1/2, z-1/2' _cell_length_a 18.8106(12) _cell_length_b 6.9928(5) _cell_length_c 13.7165(9) _cell_angle_alpha 90.00 _cell_angle_beta 109.118(3) _cell_angle_gamma 90.00 _cell_volume 1704.7(2) _cell_formula_units_Z 4 _cell_measurement_temperature 150(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description ? _exptl_crystal_colour ? _exptl_crystal_size_max 0.55 _exptl_crystal_size_mid 0.35 _exptl_crystal_size_min 0.17 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.400 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 760 _exptl_absorpt_coefficient_mu 0.105 _exptl_absorpt_correction_type ? _exptl_absorpt_correction_T_min ? _exptl_absorpt_correction_T_max ? _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 150(2) _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 ? _diffrn_measurement_method ? _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 31408 _diffrn_reflns_av_R_equivalents 0.0385 _diffrn_reflns_av_sigmaI/netI 0.0229 _diffrn_reflns_limit_h_min -28 _diffrn_reflns_limit_h_max 28 _diffrn_reflns_limit_k_min -10 _diffrn_reflns_limit_k_max 10 _diffrn_reflns_limit_l_min -20 _diffrn_reflns_limit_l_max 21 _diffrn_reflns_theta_min 3.44 _diffrn_reflns_theta_max 33.14 _reflns_number_total 6482 _reflns_number_gt 5100 _reflns_threshold_expression >2sigma(I) _computing_data_collection ? _computing_cell_refinement ? _computing_data_reduction ? _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics ? _computing_publication_material ? _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^)+(0.0760P)^2^+0.5428P] 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 6482 _refine_ls_number_parameters 332 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0643 _refine_ls_R_factor_gt 0.0481 _refine_ls_wR_factor_ref 0.1433 _refine_ls_wR_factor_gt 0.1272 _refine_ls_goodness_of_fit_ref 1.037 _refine_ls_restrained_S_all 1.037 _refine_ls_shift/su_max 0.012 _refine_ls_shift/su_mean 0.001 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 0.30600(5) 0.28719(11) 0.11290(7) 0.02543(17) Uani 1 1 d . . . O2 O 0.29082(5) 0.04637(12) -0.00339(6) 0.02767(18) Uani 1 1 d . . . O3 O 0.22641(4) -0.03378(10) 0.17852(6) 0.01991(15) Uani 1 1 d . . . O4 O 0.14352(5) -0.26950(12) 0.10667(7) 0.02734(18) Uani 1 1 d . . . O5 O -0.07572(5) 0.57377(13) 0.11027(9) 0.0354(2) Uani 1 1 d . . . O6 O -0.14068(5) 0.33221(14) 0.13292(8) 0.0321(2) Uani 1 1 d . . . N1 N -0.08347(5) 0.40225(14) 0.12343(8) 0.02450(19) Uani 1 1 d . . . C1 C 0.26119(7) 0.36456(18) 0.01635(10) 0.0306(2) Uani 1 1 d . . . H1A H 0.2897(13) 0.460(3) -0.0120(18) 0.060(6) Uiso 1 1 d . . . H1B H 0.2196(11) 0.432(3) 0.0260(16) 0.047(5) Uiso 1 1 d . . . C2A C 0.2492(3) 0.2019(9) -0.0613(5) 0.0337(10) Uani 0.50 1 d P . . H2AB H 0.269(2) 0.222(5) -0.118(3) 0.040(9) Uiso 0.50 1 d P . . H2 H 0.2126(17) 0.183(4) -0.108(2) 0.079(8) Uiso 1 1 d . . . C2B C 0.2325(3) 0.1830(8) -0.0442(4) 0.0281(8) Uani 0.50 1 d P . . H2BB H 0.186(2) 0.140(5) -0.038(3) 0.030(8) Uiso 0.50 1 d P . . C3 C 0.34076(6) 0.12050(14) 0.09127(8) 0.02002(18) Uani 1 1 d . . . C4 C 0.41887(7) 0.15968(18) 0.08176(11) 0.0296(2) Uani 1 1 d . . . H4A H 0.4416(10) 0.268(3) 0.1278(14) 0.037(4) Uiso 1 1 d . . . H4B H 0.4139(10) 0.192(3) 0.0125(16) 0.046(5) Uiso 1 1 d . . . C5 C 0.46519(6) -0.02372(18) 0.11727(10) 0.0262(2) Uani 1 1 d . . . H5A H 0.5119(10) 0.003(2) 0.1734(14) 0.033(4) Uiso 1 1 d . . . H5B H 0.4770(11) -0.084(3) 0.0627(16) 0.043(5) Uiso 1 1 d . . . C6 C 0.41580(6) -0.15862(15) 0.15677(8) 0.02168(19) Uani 1 1 d . . . H6A H 0.4458(9) -0.230(2) 0.2180(13) 0.026(4) Uiso 1 1 d . . . H6B H 0.3916(10) -0.255(3) 0.1019(15) 0.038(4) Uiso 1 1 d . . . C7 C 0.35489(5) -0.03198(14) 0.17757(7) 0.01714(17) Uani 1 1 d . . . C8 C 0.38537(6) 0.06502(16) 0.28405(8) 0.02230(19) Uani 1 1 d . . . H8A H 0.4343(10) 0.123(2) 0.2950(14) 0.034(4) Uiso 1 1 d . . . H8B H 0.3544(9) 0.173(2) 0.2864(13) 0.031(4) Uiso 1 1 d . . . C9 C 0.39174(7) -0.07214(18) 0.37103(9) 0.0269(2) Uani 1 1 d . . . H9 H 0.4239(9) -0.033(2) 0.4409(13) 0.032(4) Uiso 1 1 d . . . C10 C 0.35584(7) -0.23849(18) 0.35776(9) 0.0275(2) Uani 1 1 d . . . H10 H 0.3608(11) -0.321(3) 0.4143(15) 0.042(5) Uiso 1 1 d . . . C11 C 0.30558(6) -0.30976(15) 0.25539(9) 0.0246(2) Uani 1 1 d . . . H11A H 0.3293(10) -0.427(3) 0.2322(15) 0.039(5) Uiso 1 1 d . . . H11B H 0.2587(11) -0.359(3) 0.2620(15) 0.047(5) Uiso 1 1 d . . . C12 C 0.28710(5) -0.15836(14) 0.17047(8) 0.01863(17) Uani 1 1 d . . . H12 H 0.2690(9) -0.221(2) 0.1035(12) 0.024(4) Uiso 1 1 d . . . C13 C 0.15725(5) -0.10814(15) 0.14014(8) 0.02012(18) Uani 1 1 d . . . C14 C 0.09693(5) 0.03121(14) 0.14048(8) 0.01925(18) Uani 1 1 d . . . C15 C 0.10918(6) 0.22799(15) 0.14555(9) 0.0231(2) Uani 1 1 d . . . H15 H 0.1573(10) 0.279(3) 0.1491(14) 0.034(4) Uiso 1 1 d . . . C16 C 0.04960(6) 0.35188(16) 0.13835(10) 0.0250(2) Uani 1 1 d . . . H16 H 0.0585(10) 0.488(3) 0.1397(14) 0.036(4) Uiso 1 1 d . . . C17 C -0.02016(5) 0.27365(15) 0.12986(8) 0.02054(18) Uani 1 1 d . . . C18 C -0.03290(6) 0.07869(16) 0.12692(9) 0.0230(2) Uani 1 1 d . . . H18 H -0.0806(10) 0.029(3) 0.1204(14) 0.035(4) Uiso 1 1 d . . . C19 C 0.02597(6) -0.04319(16) 0.13034(9) 0.0231(2) Uani 1 1 d . . . H19 H 0.0191(9) -0.178(2) 0.1252(13) 0.035(4) 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 O1 0.0276(4) 0.0170(3) 0.0287(4) 0.0003(3) 0.0052(3) 0.0056(3) O2 0.0323(4) 0.0251(4) 0.0204(4) -0.0013(3) 0.0015(3) 0.0058(3) O3 0.0147(3) 0.0188(3) 0.0265(4) -0.0028(3) 0.0071(3) -0.0003(2) O4 0.0218(4) 0.0207(4) 0.0378(5) -0.0059(3) 0.0075(3) -0.0025(3) O5 0.0270(4) 0.0221(4) 0.0541(6) 0.0025(4) 0.0094(4) 0.0043(3) O6 0.0193(4) 0.0360(5) 0.0434(5) 0.0005(4) 0.0134(3) 0.0019(3) N1 0.0183(4) 0.0253(4) 0.0281(4) 0.0004(3) 0.0052(3) 0.0028(3) C1 0.0322(6) 0.0262(5) 0.0321(6) 0.0080(4) 0.0086(5) 0.0096(4) C2A 0.029(2) 0.0308(16) 0.032(2) 0.0092(13) -0.0013(15) 0.0006(15) C2B 0.0233(19) 0.0260(16) 0.0280(18) 0.0009(12) -0.0014(12) 0.0026(13) C3 0.0193(4) 0.0183(4) 0.0218(4) 0.0008(3) 0.0058(3) 0.0019(3) C4 0.0237(5) 0.0302(6) 0.0376(6) 0.0110(5) 0.0136(4) 0.0020(4) C5 0.0200(5) 0.0295(5) 0.0317(5) 0.0008(4) 0.0121(4) 0.0012(4) C6 0.0203(4) 0.0216(4) 0.0252(5) 0.0029(4) 0.0103(4) 0.0053(3) C7 0.0159(4) 0.0171(4) 0.0186(4) 0.0002(3) 0.0058(3) 0.0012(3) C8 0.0221(4) 0.0222(5) 0.0215(4) -0.0032(3) 0.0055(4) -0.0025(3) C9 0.0289(5) 0.0314(5) 0.0196(5) -0.0010(4) 0.0067(4) 0.0023(4) C10 0.0314(5) 0.0292(5) 0.0237(5) 0.0055(4) 0.0115(4) 0.0035(4) C11 0.0245(5) 0.0187(4) 0.0304(5) 0.0039(4) 0.0087(4) 0.0001(4) C12 0.0171(4) 0.0161(4) 0.0229(4) -0.0016(3) 0.0067(3) 0.0012(3) C13 0.0167(4) 0.0196(4) 0.0240(4) -0.0001(3) 0.0066(3) -0.0009(3) C14 0.0157(4) 0.0195(4) 0.0220(4) 0.0002(3) 0.0054(3) -0.0011(3) C15 0.0167(4) 0.0199(4) 0.0334(5) 0.0008(4) 0.0091(4) -0.0019(3) C16 0.0195(4) 0.0189(5) 0.0371(6) 0.0014(4) 0.0100(4) -0.0012(3) C17 0.0158(4) 0.0215(4) 0.0236(4) 0.0015(3) 0.0055(3) 0.0019(3) C18 0.0157(4) 0.0232(5) 0.0296(5) 0.0007(4) 0.0069(4) -0.0022(3) C19 0.0171(4) 0.0199(4) 0.0320(5) 0.0000(4) 0.0074(4) -0.0026(3) _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 C3 1.4146(13) . ? O1 C1 1.4233(14) . ? O2 C2A 1.421(6) . ? O2 C2B 1.424(5) . ? O2 C3 1.4276(13) . ? O3 C13 1.3384(12) . ? O3 C12 1.4687(12) . ? O4 C13 1.2137(13) . ? O5 N1 1.2287(13) . ? O6 N1 1.2274(13) . ? N1 C17 1.4716(13) . ? C1 C2B 1.517(6) . ? C1 C2A 1.524(7) . ? C1 H1A 1.01(2) . ? C1 H1B 0.96(2) . ? C2A H2AB 0.98(4) . ? C2A H2 0.79(3) . ? C2A H2BB 1.40(4) . ? C2B H2AB 1.42(4) . ? C2B H2 0.84(3) . ? C2B H2BB 0.96(4) . ? C3 C4 1.5416(15) . ? C3 C7 1.5501(14) . ? C4 C5 1.5373(17) . ? C4 H4A 0.988(19) . ? C4 H4B 0.95(2) . ? C5 C6 1.5414(15) . ? C5 H5A 0.979(18) . ? C5 H5B 0.94(2) . ? C6 C7 1.5469(13) . ? C6 H6A 0.982(16) . ? C6 H6B 1.001(19) . ? C7 C12 1.5280(13) . ? C7 C8 1.5407(14) . ? C8 C9 1.5047(16) . ? C8 H8A 0.970(18) . ? C8 H8B 0.961(17) . ? C9 C10 1.3273(18) . ? C9 H9 0.990(17) . ? C10 C11 1.4981(17) . ? C10 H10 0.95(2) . ? C11 C12 1.5275(15) . ? C11 H11A 1.031(19) . ? C11 H11B 0.98(2) . ? C12 H12 0.973(16) . ? C13 C14 1.4968(14) . ? C14 C15 1.3931(14) . ? C14 C19 1.3964(14) . ? C15 C16 1.3943(15) . ? C15 H15 0.960(17) . ? C16 C17 1.3909(14) . ? C16 H16 0.962(18) . ? C17 C18 1.3825(15) . ? C18 C19 1.3861(15) . ? C18 H18 0.940(18) . ? C19 H19 0.951(17) . ? 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 C3 O1 C1 106.96(9) . . ? C2A O2 C2B 18.98(19) . . ? C2A O2 C3 108.0(3) . . ? C2B O2 C3 107.9(2) . . ? C13 O3 C12 114.79(8) . . ? O6 N1 O5 123.74(10) . . ? O6 N1 C17 118.04(9) . . ? O5 N1 C17 118.21(9) . . ? O1 C1 C2B 100.8(2) . . ? O1 C1 C2A 105.9(2) . . ? C2B C1 C2A 17.75(17) . . ? O1 C1 H1A 112.5(13) . . ? C2B C1 H1A 118.7(13) . . ? C2A C1 H1A 101.5(13) . . ? O1 C1 H1B 108.6(12) . . ? C2B C1 H1B 109.0(12) . . ? C2A C1 H1B 121.5(12) . . ? H1A C1 H1B 106.8(17) . . ? O2 C2A C1 104.6(4) . . ? O2 C2A H2AB 106(2) . . ? C1 C2A H2AB 116(2) . . ? O2 C2A H2 121(2) . . ? C1 C2A H2 126(2) . . ? H2AB C2A H2 80(3) . . ? O2 C2A H2BB 89.4(14) . . ? C1 C2A H2BB 90.8(15) . . ? H2AB C2A H2BB 143(3) . . ? H2 C2A H2BB 64(3) . . ? O2 C2B C1 104.8(3) . . ? O2 C2B H2AB 85.5(16) . . ? C1 C2B H2AB 93.5(16) . . ? O2 C2B H2 116(2) . . ? C1 C2B H2 122(2) . . ? H2AB C2B H2 53(2) . . ? O2 C2B H2BB 111(2) . . ? C1 C2B H2BB 113(2) . . ? H2AB C2B H2BB 142(3) . . ? H2 C2B H2BB 89(3) . . ? O1 C3 O2 106.16(8) . . ? O1 C3 C4 112.96(9) . . ? O2 C3 C4 110.43(9) . . ? O1 C3 C7 112.46(8) . . ? O2 C3 C7 110.00(8) . . ? C4 C3 C7 104.90(8) . . ? C5 C4 C3 106.37(9) . . ? C5 C4 H4A 110.7(11) . . ? C3 C4 H4A 107.8(11) . . ? C5 C4 H4B 112.1(12) . . ? C3 C4 H4B 110.0(11) . . ? H4A C4 H4B 109.6(16) . . ? C4 C5 C6 106.12(9) . . ? C4 C5 H5A 110.9(10) . . ? C6 C5 H5A 109.3(10) . . ? C4 C5 H5B 112.0(12) . . ? C6 C5 H5B 109.4(12) . . ? H5A C5 H5B 109.0(15) . . ? C5 C6 C7 106.41(8) . . ? C5 C6 H6A 111.6(9) . . ? C7 C6 H6A 112.7(9) . . ? C5 C6 H6B 109.0(11) . . ? C7 C6 H6B 109.9(10) . . ? H6A C6 H6B 107.1(14) . . ? C12 C7 C8 111.02(8) . . ? C12 C7 C6 108.07(8) . . ? C8 C7 C6 111.02(8) . . ? C12 C7 C3 114.73(8) . . ? C8 C7 C3 109.79(8) . . ? C6 C7 C3 101.83(8) . . ? C9 C8 C7 112.29(9) . . ? C9 C8 H8A 108.5(11) . . ? C7 C8 H8A 111.7(11) . . ? C9 C8 H8B 111.5(10) . . ? C7 C8 H8B 109.6(10) . . ? H8A C8 H8B 102.8(14) . . ? C10 C9 C8 123.03(10) . . ? C10 C9 H9 119.9(10) . . ? C8 C9 H9 117.1(10) . . ? C9 C10 C11 123.83(10) . . ? C9 C10 H10 120.9(12) . . ? C11 C10 H10 115.3(12) . . ? C10 C11 C12 113.60(9) . . ? C10 C11 H11A 110.5(10) . . ? C12 C11 H11A 109.1(10) . . ? C10 C11 H11B 110.0(12) . . ? C12 C11 H11B 109.1(12) . . ? H11A C11 H11B 104.1(15) . . ? O3 C12 C11 110.01(8) . . ? O3 C12 C7 107.76(7) . . ? C11 C12 C7 112.06(8) . . ? O3 C12 H12 107.3(9) . . ? C11 C12 H12 109.3(9) . . ? C7 C12 H12 110.3(9) . . ? O4 C13 O3 124.68(9) . . ? O4 C13 C14 122.60(9) . . ? O3 C13 C14 112.71(8) . . ? C15 C14 C19 120.67(9) . . ? C15 C14 C13 122.01(9) . . ? C19 C14 C13 117.25(9) . . ? C14 C15 C16 119.62(9) . . ? C14 C15 H15 120.7(11) . . ? C16 C15 H15 119.5(11) . . ? C17 C16 C15 118.42(10) . . ? C17 C16 H16 122.8(11) . . ? C15 C16 H16 118.7(11) . . ? C18 C17 C16 122.69(9) . . ? C18 C17 N1 118.14(9) . . ? C16 C17 N1 119.17(9) . . ? C17 C18 C19 118.45(9) . . ? C17 C18 H18 121.2(11) . . ? C19 C18 H18 120.3(11) . . ? C18 C19 C14 120.09(10) . . ? C18 C19 H19 121.3(10) . . ? C14 C19 H19 118.6(10) . . ? _diffrn_measured_fraction_theta_max 0.997 _diffrn_reflns_theta_full 33.14 _diffrn_measured_fraction_theta_full 0.997 _refine_diff_density_max 0.517 _refine_diff_density_min -0.289 _refine_diff_density_rms 0.064 "#=END" data_43 _database_code_CSD 161067 _audit_creation_method SHELXL-97 _chemical_name_systematic ; cis-8,8-ethylenedioxospiro[4,6]undecan-4-en-1-yl p-nitrobenzoate ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C20 H23 N O6' _chemical_formula_weight 373.39 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 ? _symmetry_space_group_name_H-M P2(1)/c loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y-1/2, z-1/2' _cell_length_a 19.2045(19) _cell_length_b 6.5910(7) _cell_length_c 15.0144(15) _cell_angle_alpha 90.00 _cell_angle_beta 109.515(4) _cell_angle_gamma 90.00 _cell_volume 1791.3(3) _cell_formula_units_Z 4 _cell_measurement_temperature 150(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description ? _exptl_crystal_colour ? _exptl_crystal_size_max 0.5 _exptl_crystal_size_mid 0.2 _exptl_crystal_size_min 0.07 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.385 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 792 _exptl_absorpt_coefficient_mu 0.102 _exptl_absorpt_correction_type ? _exptl_absorpt_correction_T_min ? _exptl_absorpt_correction_T_max ? _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 150(2) _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 ? _diffrn_measurement_method ? _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 26933 _diffrn_reflns_av_R_equivalents 0.0573 _diffrn_reflns_av_sigmaI/netI 0.0324 _diffrn_reflns_limit_h_min -25 _diffrn_reflns_limit_h_max 24 _diffrn_reflns_limit_k_min -8 _diffrn_reflns_limit_k_max 8 _diffrn_reflns_limit_l_min -20 _diffrn_reflns_limit_l_max 19 _diffrn_reflns_theta_min 2.25 _diffrn_reflns_theta_max 28.28 _reflns_number_total 4444 _reflns_number_gt 3235 _reflns_threshold_expression >2sigma(I) _computing_data_collection ? _computing_cell_refinement ? _computing_data_reduction ? _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics ? _computing_publication_material ? _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^)+(0.0476P)^2^+0.5848P] 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 4444 _refine_ls_number_parameters 336 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0688 _refine_ls_R_factor_gt 0.0437 _refine_ls_wR_factor_ref 0.1076 _refine_ls_wR_factor_gt 0.0983 _refine_ls_goodness_of_fit_ref 1.025 _refine_ls_restrained_S_all 1.025 _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 O1 O 0.20619(6) -0.18394(16) 0.41499(8) 0.0304(3) Uani 1 1 d . . . O2 O 0.21634(6) -0.46816(17) 0.50413(7) 0.0309(3) Uani 1 1 d . . . O3 O 0.27503(5) -0.52366(15) 0.33842(7) 0.0235(2) Uani 1 1 d . . . O4 O 0.35331(6) -0.77370(17) 0.41328(9) 0.0368(3) Uani 1 1 d . . . O5 O 0.63193(6) -0.2050(2) 0.34008(9) 0.0396(3) Uani 1 1 d . . . O6 O 0.57422(6) 0.06894(18) 0.35424(9) 0.0363(3) Uani 1 1 d . . . N1 N 0.57893(7) -0.1160(2) 0.35028(9) 0.0286(3) Uani 1 1 d . . . C1 C 0.26830(11) -0.1579(3) 0.49978(12) 0.0390(4) Uani 1 1 d . . . H1A H 0.2680(12) -0.021(4) 0.5206(16) 0.054(6) Uiso 1 1 d . . . H1B H 0.3151(12) -0.188(3) 0.4846(15) 0.051(6) Uiso 1 1 d . . . C2 C 0.25678(10) -0.3124(3) 0.56703(12) 0.0347(4) Uani 1 1 d . . . H2A H 0.3032(11) -0.372(3) 0.6110(14) 0.039(5) Uiso 1 1 d . . . H2B H 0.2268(10) -0.258(3) 0.6031(13) 0.036(5) Uiso 1 1 d . . . C3 C 0.16820(8) -0.3644(2) 0.42414(11) 0.0249(3) Uani 1 1 d . . . C4 C 0.09368(10) -0.3154(3) 0.43733(15) 0.0409(4) Uani 1 1 d . . . H4A H 0.0775(12) -0.186(3) 0.4100(15) 0.051(6) Uiso 1 1 d . . . H4B H 0.0993(14) -0.302(4) 0.503(2) 0.076(8) Uiso 1 1 d . . . C5 C 0.04072(9) -0.4852(3) 0.38873(13) 0.0317(4) Uani 1 1 d . . . H5B H 0.0186(11) -0.552(3) 0.4285(15) 0.048(6) Uiso 1 1 d . . . H5A H -0.0023(12) -0.429(3) 0.3361(16) 0.053(6) Uiso 1 1 d . . . C6 C 0.08449(8) -0.6320(2) 0.34868(12) 0.0264(3) Uani 1 1 d . . . H6A H 0.1071(10) -0.746(3) 0.3964(14) 0.038(5) Uiso 1 1 d . . . H6B H 0.0525(11) -0.694(3) 0.2878(14) 0.042(5) Uiso 1 1 d . . . C7 C 0.14858(8) -0.5056(2) 0.33623(10) 0.0204(3) Uani 1 1 d . . . C8 C 0.12263(9) -0.3676(2) 0.24767(10) 0.0243(3) Uani 1 1 d . . . H8A H 0.0931(9) -0.257(3) 0.2621(12) 0.029(4) Uiso 1 1 d . . . H8B H 0.1663(9) -0.305(3) 0.2399(12) 0.025(4) Uiso 1 1 d . . . C9 C 0.07866(10) -0.4699(2) 0.15671(11) 0.0302(3) Uani 1 1 d . . . H9 H 0.0283(11) -0.426(3) 0.1256(13) 0.034(5) Uiso 1 1 d . . . C10 C 0.10431(10) -0.6166(3) 0.11627(12) 0.0344(4) Uani 1 1 d . . . H10 H 0.0705(11) -0.672(3) 0.0564(14) 0.040(5) Uiso 1 1 d . . . C11 C 0.17973(10) -0.7077(3) 0.15718(13) 0.0377(4) Uani 1 1 d . . . H11A H 0.1871(11) -0.813(3) 0.1152(15) 0.049(6) Uiso 1 1 d . . . H11B H 0.2184(12) -0.602(3) 0.1608(15) 0.050(6) Uiso 1 1 d . . . C12 C 0.19556(9) -0.7998(2) 0.25562(12) 0.0300(3) Uani 1 1 d . . . H12A H 0.2375(11) -0.888(3) 0.2689(13) 0.037(5) Uiso 1 1 d . . . H12B H 0.1537(10) -0.886(3) 0.2580(12) 0.033(5) Uiso 1 1 d . . . C13 C 0.21165(8) -0.6495(2) 0.33745(11) 0.0222(3) Uani 1 1 d . . . H13 H 0.2271(9) -0.721(3) 0.3972(13) 0.027(4) Uiso 1 1 d . . . C14 C 0.34177(8) -0.6074(2) 0.37704(11) 0.0257(3) Uani 1 1 d . . . C15 C 0.40207(8) -0.4721(2) 0.36944(10) 0.0232(3) Uani 1 1 d . . . C16 C 0.47192(8) -0.5576(2) 0.38804(11) 0.0261(3) Uani 1 1 d . . . H16 H 0.4799(10) -0.698(3) 0.4067(13) 0.036(5) Uiso 1 1 d . . . C17 C 0.52983(8) -0.4426(2) 0.38044(11) 0.0260(3) Uani 1 1 d . . . H17 H 0.5759(11) -0.505(3) 0.3920(13) 0.034(5) Uiso 1 1 d . . . C18 C 0.51698(8) -0.2398(2) 0.35715(10) 0.0241(3) Uani 1 1 d . . . C19 C 0.44863(8) -0.1489(2) 0.33984(11) 0.0271(3) Uani 1 1 d . . . H19 H 0.4415(10) -0.010(3) 0.3221(12) 0.032(5) Uiso 1 1 d . . . C20 C 0.39049(8) -0.2675(2) 0.34502(11) 0.0259(3) Uani 1 1 d . . . H20 H 0.3440(10) -0.211(3) 0.3355(13) 0.033(5) 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 O1 0.0348(6) 0.0216(5) 0.0296(6) -0.0004(4) 0.0038(5) -0.0067(5) O2 0.0380(6) 0.0294(6) 0.0232(5) 0.0009(4) 0.0073(5) -0.0056(5) O3 0.0195(5) 0.0193(5) 0.0325(6) 0.0016(4) 0.0096(4) -0.0008(4) O4 0.0277(6) 0.0262(6) 0.0546(8) 0.0117(5) 0.0112(5) 0.0024(5) O5 0.0247(6) 0.0452(7) 0.0526(8) 0.0015(6) 0.0177(5) -0.0003(5) O6 0.0310(6) 0.0296(6) 0.0460(7) 0.0007(5) 0.0097(5) -0.0067(5) N1 0.0215(6) 0.0335(7) 0.0284(7) -0.0002(6) 0.0052(5) -0.0036(5) C1 0.0446(11) 0.0425(11) 0.0273(8) -0.0069(7) 0.0086(8) -0.0183(8) C2 0.0347(9) 0.0383(10) 0.0282(8) -0.0060(7) 0.0067(7) -0.0060(8) C3 0.0261(7) 0.0226(7) 0.0260(7) -0.0022(6) 0.0089(6) -0.0016(6) C4 0.0313(9) 0.0486(12) 0.0458(11) -0.0190(9) 0.0168(8) -0.0011(8) C5 0.0269(8) 0.0325(9) 0.0402(9) 0.0010(7) 0.0171(7) 0.0000(7) C6 0.0236(7) 0.0269(8) 0.0311(8) -0.0019(6) 0.0123(6) -0.0063(6) C7 0.0201(7) 0.0180(7) 0.0241(7) -0.0015(5) 0.0087(5) -0.0018(5) C8 0.0235(7) 0.0207(7) 0.0281(8) -0.0001(6) 0.0080(6) -0.0001(6) C9 0.0313(9) 0.0295(8) 0.0265(8) 0.0021(6) 0.0052(7) -0.0035(7) C10 0.0424(10) 0.0344(9) 0.0256(8) -0.0024(7) 0.0102(7) -0.0085(7) C11 0.0435(10) 0.0373(10) 0.0383(9) -0.0138(8) 0.0219(8) -0.0028(8) C12 0.0283(8) 0.0197(7) 0.0430(9) -0.0057(6) 0.0130(7) 0.0005(6) C13 0.0208(7) 0.0169(7) 0.0299(8) 0.0018(6) 0.0099(6) -0.0023(5) C14 0.0235(7) 0.0230(8) 0.0306(8) -0.0010(6) 0.0092(6) 0.0011(6) C15 0.0210(7) 0.0232(7) 0.0249(7) -0.0026(6) 0.0070(6) -0.0012(6) C16 0.0251(8) 0.0232(8) 0.0285(7) -0.0011(6) 0.0070(6) 0.0022(6) C17 0.0194(7) 0.0290(8) 0.0284(8) -0.0016(6) 0.0064(6) 0.0029(6) C18 0.0202(7) 0.0273(8) 0.0243(7) -0.0033(6) 0.0066(6) -0.0044(6) C19 0.0251(8) 0.0216(8) 0.0339(8) -0.0007(6) 0.0089(6) -0.0004(6) C20 0.0198(7) 0.0237(7) 0.0340(8) -0.0015(6) 0.0086(6) 0.0021(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 O1 C3 1.4256(18) . ? O1 C1 1.435(2) . ? O2 C3 1.4223(19) . ? O2 C2 1.435(2) . ? O3 C14 1.3369(18) . ? O3 C13 1.4689(16) . ? O4 C14 1.2106(19) . ? O5 N1 1.2278(17) . ? O6 N1 1.2253(18) . ? N1 C18 1.4742(19) . ? C1 C2 1.501(3) . ? C1 H1A 0.96(2) . ? C1 H1B 1.02(2) . ? C2 H2A 0.99(2) . ? C2 H2B 0.98(2) . ? C3 C4 1.543(2) . ? C3 C7 1.555(2) . ? C4 C5 1.524(3) . ? C4 H4A 0.95(2) . ? C4 H4B 0.96(3) . ? C5 C6 1.530(2) . ? C5 H5B 0.95(2) . ? C5 H5A 1.00(2) . ? C6 C7 1.549(2) . ? C6 H6A 1.03(2) . ? C6 H6B 1.00(2) . ? C7 C13 1.5338(19) . ? C7 C8 1.550(2) . ? C8 C9 1.504(2) . ? C8 H8A 0.993(18) . ? C8 H8B 0.974(17) . ? C9 C10 1.321(2) . ? C9 H9 0.968(19) . ? C10 C11 1.497(3) . ? C10 H10 0.99(2) . ? C11 C12 1.531(3) . ? C11 H11A 0.98(2) . ? C11 H11B 1.01(2) . ? C12 C13 1.527(2) . ? C12 H12A 0.96(2) . ? C12 H12B 0.995(19) . ? C13 H13 0.968(18) . ? C14 C15 1.496(2) . ? C15 C16 1.394(2) . ? C15 C20 1.396(2) . ? C16 C17 1.382(2) . ? C16 H16 0.961(19) . ? C17 C18 1.383(2) . ? C17 H17 0.938(19) . ? C18 C19 1.386(2) . ? C19 C20 1.386(2) . ? C19 H19 0.952(19) . ? C20 H20 0.932(19) . ? 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 C3 O1 C1 108.34(12) . . ? C3 O2 C2 105.54(12) . . ? C14 O3 C13 116.24(11) . . ? O6 N1 O5 123.97(14) . . ? O6 N1 C18 118.22(13) . . ? O5 N1 C18 117.81(13) . . ? O1 C1 C2 104.48(14) . . ? O1 C1 H1A 108.0(14) . . ? C2 C1 H1A 113.7(14) . . ? O1 C1 H1B 108.2(12) . . ? C2 C1 H1B 111.0(12) . . ? H1A C1 H1B 111.1(18) . . ? O2 C2 C1 102.21(13) . . ? O2 C2 H2A 108.9(11) . . ? C1 C2 H2A 114.3(11) . . ? O2 C2 H2B 109.6(11) . . ? C1 C2 H2B 111.8(11) . . ? H2A C2 H2B 109.7(16) . . ? O2 C3 O1 105.87(11) . . ? O2 C3 C4 111.17(14) . . ? O1 C3 C4 111.36(13) . . ? O2 C3 C7 109.50(12) . . ? O1 C3 C7 113.84(12) . . ? C4 C3 C7 105.19(12) . . ? C5 C4 C3 106.51(14) . . ? C5 C4 H4A 112.5(13) . . ? C3 C4 H4A 108.3(13) . . ? C5 C4 H4B 112.8(15) . . ? C3 C4 H4B 111.1(15) . . ? H4A C4 H4B 106(2) . . ? C4 C5 C6 106.62(13) . . ? C4 C5 H5B 114.0(13) . . ? C6 C5 H5B 111.9(13) . . ? C4 C5 H5A 110.2(12) . . ? C6 C5 H5A 109.9(12) . . ? H5B C5 H5A 104.2(17) . . ? C5 C6 C7 105.69(12) . . ? C5 C6 H6A 110.4(10) . . ? C7 C6 H6A 108.0(11) . . ? C5 C6 H6B 111.5(11) . . ? C7 C6 H6B 112.3(11) . . ? H6A C6 H6B 108.9(15) . . ? C13 C7 C6 108.79(11) . . ? C13 C7 C8 113.56(12) . . ? C6 C7 C8 112.24(12) . . ? C13 C7 C3 113.17(12) . . ? C6 C7 C3 101.34(11) . . ? C8 C7 C3 107.12(11) . . ? C9 C8 C7 115.98(12) . . ? C9 C8 H8A 109.9(10) . . ? C7 C8 H8A 106.8(10) . . ? C9 C8 H8B 108.9(10) . . ? C7 C8 H8B 107.8(10) . . ? H8A C8 H8B 107.1(14) . . ? C10 C9 C8 124.26(16) . . ? C10 C9 H9 117.7(11) . . ? C8 C9 H9 118.0(11) . . ? C9 C10 C11 124.26(16) . . ? C9 C10 H10 117.3(11) . . ? C11 C10 H10 118.4(11) . . ? C10 C11 C12 114.08(14) . . ? C10 C11 H11A 110.3(12) . . ? C12 C11 H11A 108.5(12) . . ? C10 C11 H11B 109.9(12) . . ? C12 C11 H11B 108.5(12) . . ? H11A C11 H11B 105.1(17) . . ? C13 C12 C11 116.16(13) . . ? C13 C12 H12A 107.2(11) . . ? C11 C12 H12A 108.9(11) . . ? C13 C12 H12B 106.9(10) . . ? C11 C12 H12B 111.1(10) . . ? H12A C12 H12B 106.1(15) . . ? O3 C13 C12 108.57(12) . . ? O3 C13 C7 107.41(11) . . ? C12 C13 C7 116.41(12) . . ? O3 C13 H13 105.6(10) . . ? C12 C13 H13 110.3(10) . . ? C7 C13 H13 108.0(10) . . ? O4 C14 O3 125.02(14) . . ? O4 C14 C15 122.94(14) . . ? O3 C14 C15 112.03(12) . . ? C16 C15 C20 120.09(14) . . ? C16 C15 C14 117.46(13) . . ? C20 C15 C14 122.45(13) . . ? C17 C16 C15 120.56(14) . . ? C17 C16 H16 119.8(11) . . ? C15 C16 H16 119.7(11) . . ? C16 C17 C18 118.08(14) . . ? C16 C17 H17 118.6(11) . . ? C18 C17 H17 123.4(11) . . ? C17 C18 C19 122.90(14) . . ? C17 C18 N1 118.20(13) . . ? C19 C18 N1 118.91(14) . . ? C18 C19 C20 118.40(14) . . ? C18 C19 H19 120.5(11) . . ? C20 C19 H19 121.0(11) . . ? C19 C20 C15 119.93(14) . . ? C19 C20 H20 120.9(11) . . ? C15 C20 H20 119.0(11) . . ? _diffrn_measured_fraction_theta_max 1.000 _diffrn_reflns_theta_full 28.28 _diffrn_measured_fraction_theta_full 1.000 _refine_diff_density_max 0.328 _refine_diff_density_min -0.187 _refine_diff_density_rms 0.042 "#=END" data_44 _database_code_CSD 161068 _audit_creation_method SHELXL-97 _chemical_name_systematic ; cis-7,7-ethylenedioxospiro[5,5]undecan-3-en-1-yl p-nitrobenzoate ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C20 H23 N O6' _chemical_formula_weight 373.39 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 ? _symmetry_space_group_name_H-M P2(1)/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 6.8560(7) _cell_length_b 12.8358(14) _cell_length_c 20.535(2) _cell_angle_alpha 90.00 _cell_angle_beta 96.055(4) _cell_angle_gamma 90.00 _cell_volume 1797.1(3) _cell_formula_units_Z 4 _cell_measurement_temperature 150(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description ? _exptl_crystal_colour ? _exptl_crystal_size_max ? _exptl_crystal_size_mid ? _exptl_crystal_size_min ? _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.380 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 792 _exptl_absorpt_coefficient_mu 0.102 _exptl_absorpt_correction_type ? _exptl_absorpt_correction_T_min ? _exptl_absorpt_correction_T_max ? _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 150(2) _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 ? _diffrn_measurement_method ? _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 38813 _diffrn_reflns_av_R_equivalents 0.0222 _diffrn_reflns_av_sigmaI/netI 0.0171 _diffrn_reflns_limit_h_min -11 _diffrn_reflns_limit_h_max 11 _diffrn_reflns_limit_k_min -20 _diffrn_reflns_limit_k_max 20 _diffrn_reflns_limit_l_min -31 _diffrn_reflns_limit_l_max 33 _diffrn_reflns_theta_min 1.87 _diffrn_reflns_theta_max 35.84 _reflns_number_total 8006 _reflns_number_gt 6221 _reflns_threshold_expression >2sigma(I) _computing_data_collection ? _computing_cell_refinement ? _computing_data_reduction ? _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics ? _computing_publication_material ? _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^)+(0.0670P)^2^+0.4200P] 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 8006 _refine_ls_number_parameters 336 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0637 _refine_ls_R_factor_gt 0.0467 _refine_ls_wR_factor_ref 0.1360 _refine_ls_wR_factor_gt 0.1240 _refine_ls_goodness_of_fit_ref 1.048 _refine_ls_restrained_S_all 1.048 _refine_ls_shift/su_max 0.007 _refine_ls_shift/su_mean 0.001 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 1.06314(11) 0.42045(6) 0.41197(3) 0.02761(14) Uani 1 1 d . . . O2 O 0.98921(11) 0.40375(6) 0.30139(3) 0.02896(14) Uani 1 1 d . . . O3 O 0.92139(9) 0.58566(5) 0.23481(3) 0.02362(13) Uani 1 1 d . . . O4 O 0.63263(11) 0.52378(8) 0.18736(4) 0.0405(2) Uani 1 1 d . . . O5 O 1.42160(13) 0.37469(8) -0.00367(5) 0.0445(2) Uani 1 1 d . . . O6 O 1.15999(16) 0.29309(8) -0.04395(5) 0.0528(3) Uani 1 1 d . . . N1 N 1.24707(14) 0.35287(7) -0.00410(4) 0.03221(18) Uani 1 1 d . . . C1 C 1.12573(18) 0.31865(8) 0.39537(6) 0.0347(2) Uani 1 1 d . . . H1A H 1.256(2) 0.3074(13) 0.4169(8) 0.042(4) Uiso 1 1 d . . . H1B H 1.032(3) 0.2659(15) 0.4063(9) 0.056(5) Uiso 1 1 d . . . C2 C 1.1246(2) 0.32455(12) 0.32170(7) 0.0472(3) Uani 1 1 d . . . H2B H 1.094(3) 0.2636(16) 0.3006(10) 0.063(5) Uiso 1 1 d . . . H2A H 1.264(3) 0.3468(17) 0.3063(11) 0.078(6) Uiso 1 1 d . . . C3 C 0.93053(13) 0.45584(7) 0.35797(4) 0.02202(15) Uani 1 1 d . . . C4 C 0.71981(14) 0.42408(8) 0.36718(5) 0.02724(17) Uani 1 1 d . . . H4A H 0.716(2) 0.3482(12) 0.3713(7) 0.034(3) Uiso 1 1 d . . . H4B H 0.634(2) 0.4433(11) 0.3275(7) 0.028(3) Uiso 1 1 d . . . C5 C 0.64695(15) 0.47578(8) 0.42744(5) 0.02964(19) Uani 1 1 d . . . H5A H 0.506(2) 0.4572(13) 0.4295(8) 0.044(4) Uiso 1 1 d . . . H5B H 0.723(2) 0.4479(12) 0.4665(7) 0.034(4) Uiso 1 1 d . . . C6 C 0.67344(14) 0.59389(8) 0.42603(5) 0.02698(17) Uani 1 1 d . . . H6A H 0.587(2) 0.6246(11) 0.3899(7) 0.034(4) Uiso 1 1 d . . . H6B H 0.635(2) 0.6262(12) 0.4664(8) 0.037(4) Uiso 1 1 d . . . C7 C 0.88507(13) 0.62234(7) 0.41675(4) 0.02277(15) Uani 1 1 d . . . H7A H 0.900(2) 0.6988(11) 0.4173(7) 0.031(3) Uiso 1 1 d . . . H7B H 0.975(2) 0.5947(12) 0.4552(7) 0.038(4) Uiso 1 1 d . . . C8 C 0.95566(11) 0.57570(7) 0.35343(4) 0.01942(14) Uani 1 1 d . . . C9 C 1.17158(12) 0.60558(7) 0.34990(4) 0.02334(15) Uani 1 1 d . . . H9A H 1.233(2) 0.5620(11) 0.3172(7) 0.030(3) Uiso 1 1 d . . . H9B H 1.248(2) 0.5926(11) 0.3926(7) 0.033(3) Uiso 1 1 d . . . C10 C 1.19569(14) 0.71847(8) 0.33182(5) 0.02785(17) Uani 1 1 d . . . H10 H 1.330(2) 0.7468(12) 0.3411(7) 0.037(4) Uiso 1 1 d . . . C11 C 1.04957(15) 0.77914(8) 0.30644(5) 0.02950(18) Uani 1 1 d . . . H11 H 1.071(2) 0.8536(13) 0.2958(8) 0.045(4) Uiso 1 1 d . . . C12 C 0.84314(14) 0.74018(8) 0.29112(5) 0.02716(17) Uani 1 1 d . . . H12A H 0.753(2) 0.7698(11) 0.3206(7) 0.034(3) Uiso 1 1 d . . . H12B H 0.786(2) 0.7630(12) 0.2479(8) 0.038(4) Uiso 1 1 d . . . C13 C 0.83329(12) 0.62194(7) 0.29263(4) 0.02144(14) Uani 1 1 d . . . H13 H 0.6966(19) 0.5999(10) 0.2879(6) 0.024(3) Uiso 1 1 d . . . C14 C 0.80870(13) 0.53498(7) 0.18872(4) 0.02398(16) Uani 1 1 d . . . C15 C 0.92685(13) 0.49105(7) 0.13777(4) 0.02237(15) Uani 1 1 d . . . C16 C 0.83294(14) 0.42382(7) 0.09100(4) 0.02558(16) Uani 1 1 d . . . H16 H 0.695(2) 0.4085(11) 0.0918(7) 0.034(4) Uiso 1 1 d . . . C17 C 0.93732(15) 0.37789(7) 0.04415(5) 0.02651(17) Uani 1 1 d . . . H17 H 0.874(2) 0.3316(12) 0.0114(7) 0.034(4) Uiso 1 1 d . . . C18 C 1.13487(14) 0.40200(7) 0.04496(4) 0.02475(16) Uani 1 1 d . . . C19 C 1.23120(14) 0.47044(8) 0.08973(5) 0.02661(17) Uani 1 1 d . . . H19 H 1.362(2) 0.4855(12) 0.0878(8) 0.039(4) Uiso 1 1 d . . . C20 C 1.12570(13) 0.51436(7) 0.13704(4) 0.02558(16) Uani 1 1 d . . . H20 H 1.193(2) 0.5614(12) 0.1699(7) 0.033(3) 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 O1 0.0312(3) 0.0281(3) 0.0230(3) 0.0026(2) 0.0004(2) 0.0068(3) O2 0.0385(4) 0.0261(3) 0.0231(3) -0.0037(2) 0.0071(3) 0.0011(3) O3 0.0214(3) 0.0325(3) 0.0167(2) -0.0022(2) 0.00090(19) -0.0047(2) O4 0.0225(3) 0.0629(6) 0.0358(4) -0.0180(4) 0.0012(3) -0.0082(3) O5 0.0342(4) 0.0549(5) 0.0452(5) -0.0148(4) 0.0085(3) 0.0044(4) O6 0.0511(5) 0.0525(6) 0.0553(6) -0.0322(5) 0.0074(4) -0.0012(4) N1 0.0362(4) 0.0289(4) 0.0312(4) -0.0051(3) 0.0023(3) 0.0064(3) C1 0.0373(5) 0.0274(4) 0.0403(5) 0.0044(4) 0.0083(4) 0.0072(4) C2 0.0478(7) 0.0519(7) 0.0408(6) -0.0126(5) -0.0003(5) 0.0228(6) C3 0.0236(4) 0.0242(4) 0.0182(3) -0.0002(3) 0.0023(3) 0.0000(3) C4 0.0266(4) 0.0282(4) 0.0273(4) 0.0018(3) 0.0046(3) -0.0058(3) C5 0.0257(4) 0.0357(5) 0.0288(4) 0.0044(4) 0.0086(3) -0.0027(3) C6 0.0230(4) 0.0338(4) 0.0250(4) -0.0001(3) 0.0066(3) 0.0015(3) C7 0.0219(4) 0.0279(4) 0.0184(3) -0.0020(3) 0.0013(3) 0.0005(3) C8 0.0168(3) 0.0239(3) 0.0172(3) -0.0003(3) 0.0003(2) -0.0006(3) C9 0.0171(3) 0.0280(4) 0.0246(4) -0.0006(3) 0.0006(3) -0.0011(3) C10 0.0242(4) 0.0299(4) 0.0294(4) -0.0021(3) 0.0025(3) -0.0065(3) C11 0.0326(5) 0.0253(4) 0.0308(4) 0.0009(3) 0.0040(3) -0.0034(3) C12 0.0277(4) 0.0273(4) 0.0259(4) 0.0036(3) 0.0001(3) 0.0030(3) C13 0.0189(3) 0.0276(4) 0.0174(3) 0.0005(3) 0.0001(2) -0.0006(3) C14 0.0235(4) 0.0279(4) 0.0199(3) -0.0007(3) -0.0012(3) -0.0033(3) C15 0.0234(4) 0.0237(4) 0.0193(3) -0.0004(3) -0.0010(3) -0.0019(3) C16 0.0259(4) 0.0261(4) 0.0238(4) -0.0009(3) -0.0019(3) -0.0044(3) C17 0.0312(4) 0.0227(4) 0.0244(4) -0.0024(3) -0.0023(3) -0.0019(3) C18 0.0293(4) 0.0213(3) 0.0231(4) -0.0004(3) 0.0005(3) 0.0037(3) C19 0.0239(4) 0.0289(4) 0.0266(4) -0.0028(3) 0.0006(3) 0.0002(3) C20 0.0241(4) 0.0282(4) 0.0237(4) -0.0039(3) -0.0007(3) -0.0030(3) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag O1 C1 1.4279(13) . ? O1 C3 1.4318(11) . ? O2 C2 1.4097(15) . ? O2 C3 1.4343(11) . ? O3 C14 1.3272(10) . ? O3 C13 1.4637(10) . ? O4 C14 1.2131(11) . ? O5 N1 1.2280(13) . ? O6 N1 1.2294(13) . ? N1 C18 1.4724(13) . ? C1 C2 1.5138(18) . ? C3 C4 1.5320(13) . ? C3 C8 1.5520(12) . ? C4 C5 1.5335(14) . ? C5 C6 1.5275(15) . ? C6 C7 1.5275(13) . ? C7 C8 1.5544(12) . ? C8 C9 1.5383(12) . ? C8 C13 1.5473(11) . ? C9 C10 1.5093(14) . ? C10 C11 1.3310(15) . ? C11 C12 1.5027(14) . ? C12 C13 1.5196(13) . ? C14 C15 1.4992(13) . ? C15 C16 1.3970(12) . ? C15 C20 1.3974(13) . ? C16 C17 1.3893(14) . ? C17 C18 1.3877(14) . ? C18 C19 1.3875(13) . ? C19 C20 1.3904(13) . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C1 O1 C3 106.72(8) . . ? C2 O2 C3 109.19(8) . . ? C14 O3 C13 118.38(7) . . ? O5 N1 O6 123.47(10) . . ? O5 N1 C18 118.45(9) . . ? O6 N1 C18 118.07(9) . . ? O1 C1 C2 102.88(9) . . ? O2 C2 C1 105.40(9) . . ? O1 C3 O2 105.67(7) . . ? O1 C3 C4 110.49(7) . . ? O2 C3 C4 108.95(7) . . ? O1 C3 C8 107.19(7) . . ? O2 C3 C8 111.78(7) . . ? C4 C3 C8 112.54(7) . . ? C3 C4 C5 112.10(8) . . ? C6 C5 C4 111.39(8) . . ? C7 C6 C5 110.86(8) . . ? C6 C7 C8 113.32(7) . . ? C9 C8 C13 108.00(7) . . ? C9 C8 C3 111.31(7) . . ? C13 C8 C3 111.99(7) . . ? C9 C8 C7 109.24(7) . . ? C13 C8 C7 109.71(7) . . ? C3 C8 C7 106.57(7) . . ? C10 C9 C8 112.44(7) . . ? C11 C10 C9 124.10(9) . . ? C10 C11 C12 122.73(9) . . ? C11 C12 C13 111.78(8) . . ? O3 C13 C12 106.15(7) . . ? O3 C13 C8 107.31(7) . . ? C12 C13 C8 112.21(7) . . ? O4 C14 O3 125.28(9) . . ? O4 C14 C15 123.29(8) . . ? O3 C14 C15 111.43(7) . . ? C16 C15 C20 120.28(8) . . ? C16 C15 C14 117.94(8) . . ? C20 C15 C14 121.77(8) . . ? C17 C16 C15 120.30(8) . . ? C18 C17 C16 118.07(8) . . ? C19 C18 C17 123.01(9) . . ? C19 C18 N1 118.56(9) . . ? C17 C18 N1 118.43(8) . . ? C18 C19 C20 118.26(9) . . ? C19 C20 C15 120.05(8) . . ? _diffrn_measured_fraction_theta_max 0.952 _diffrn_reflns_theta_full 35.84 _diffrn_measured_fraction_theta_full 0.952 _refine_diff_density_max 0.658 _refine_diff_density_min -0.492 _refine_diff_density_rms 0.049 "#=END" data_45 _database_code_CSD 161069 _audit_creation_method SHELXL-97 _chemical_name_systematic ; cis-8,8-ethylenedioxospiro[5,6]dodekan-3-en-1-yl p-nitrobenzoate ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C21 H25 N O6' _chemical_formula_weight 387.42 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 ? _symmetry_space_group_name_H-M P-1 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 8.3205(8) _cell_length_b 12.5407(11) _cell_length_c 18.9520(19) _cell_angle_alpha 99.019(4) _cell_angle_beta 98.985(4) _cell_angle_gamma 102.447(4) _cell_volume 1869.8(3) _cell_formula_units_Z 4 _cell_measurement_temperature 150(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description ? _exptl_crystal_colour ? _exptl_crystal_size_max 0.6 _exptl_crystal_size_mid 0.15 _exptl_crystal_size_min 0.01 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.376 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 824 _exptl_absorpt_coefficient_mu 0.101 _exptl_absorpt_correction_type ? _exptl_absorpt_correction_T_min ? _exptl_absorpt_correction_T_max ? _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 150(2) _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 ? _diffrn_measurement_method ? _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 14769 _diffrn_reflns_av_R_equivalents 0.0890 _diffrn_reflns_av_sigmaI/netI 0.0641 _diffrn_reflns_limit_h_min -9 _diffrn_reflns_limit_h_max 9 _diffrn_reflns_limit_k_min -13 _diffrn_reflns_limit_k_max 13 _diffrn_reflns_limit_l_min -21 _diffrn_reflns_limit_l_max 21 _diffrn_reflns_theta_min 1.70 _diffrn_reflns_theta_max 23.25 _reflns_number_total 5348 _reflns_number_gt 3722 _reflns_threshold_expression >2sigma(I) _computing_data_collection ? _computing_cell_refinement ? _computing_data_reduction ? _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics ? _computing_publication_material ? _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^)+(0.1425P)^2^+9.6810P] 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 0.005(2) _refine_ls_extinction_expression 'Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^' _refine_ls_number_reflns 5348 _refine_ls_number_parameters 706 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.1304 _refine_ls_R_factor_gt 0.0981 _refine_ls_wR_factor_ref 0.3095 _refine_ls_wR_factor_gt 0.2874 _refine_ls_goodness_of_fit_ref 1.107 _refine_ls_restrained_S_all 1.107 _refine_ls_shift/su_max 0.027 _refine_ls_shift/su_mean 0.002 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 1.0808(6) 0.1800(4) 0.0577(2) 0.0305(11) Uani 1 1 d . . . O2 O 0.9131(6) 0.2812(4) 0.1071(2) 0.0273(11) Uani 1 1 d . . . O3 O 0.6782(5) 0.1788(4) 0.1705(2) 0.0252(11) Uani 1 1 d . . . O4 O 0.7961(7) 0.2936(4) 0.2789(3) 0.0382(13) Uani 1 1 d . . . O5 O 0.3371(8) 0.5869(5) 0.0541(3) 0.0542(16) Uani 1 1 d . . . O6 O 0.3670(8) 0.6708(5) 0.1662(3) 0.0520(16) Uani 1 1 d . . . N1 N 0.3822(7) 0.5952(5) 0.1199(4) 0.0371(16) Uani 1 1 d . . . C1 C 1.0371(10) 0.2531(7) 0.0094(4) 0.0366(18) Uani 1 1 d . . . H1A H 0.929(10) 0.196(6) -0.035(4) 0.05(2) Uiso 1 1 d . . . H1B H 1.125(10) 0.276(6) -0.014(4) 0.04(2) Uiso 1 1 d . . . C2 C 0.9905(10) 0.3413(6) 0.0583(5) 0.0363(18) Uani 1 1 d . . . H2A H 1.089(9) 0.401(6) 0.076(4) 0.023(17) Uiso 1 1 d . . . H2B H 0.900(10) 0.373(6) 0.033(4) 0.04(2) Uiso 1 1 d . . . C3 C 1.0016(8) 0.1969(5) 0.1193(3) 0.0239(15) Uani 1 1 d . . . C4 C 1.1394(9) 0.2395(6) 0.1873(4) 0.0287(16) Uani 1 1 d . . . H4A H 1.079(8) 0.255(5) 0.234(4) 0.021(16) Uiso 1 1 d . . . H4B H 1.211(14) 0.305(9) 0.177(6) 0.09(3) Uiso 1 1 d . . . C5 C 1.2427(9) 0.1544(6) 0.1993(4) 0.0327(17) Uani 1 1 d . . . H5A H 1.335(8) 0.140(5) 0.160(4) 0.026(17) Uiso 1 1 d . . . H5B H 1.338(11) 0.177(7) 0.238(5) 0.05(2) Uiso 1 1 d . . . C6 C 1.1289(9) 0.0427(6) 0.2028(4) 0.0290(16) Uani 1 1 d . . . H6A H 1.090(12) 0.040(8) 0.250(6) 0.07(3) Uiso 1 1 d . . . H6B H 1.199(12) -0.007(8) 0.199(5) 0.06(3) Uiso 1 1 d . . . C7 C 0.9880(9) 0.0028(6) 0.1342(4) 0.0280(16) Uani 1 1 d . . . H7A H 0.935(10) -0.063(7) 0.132(4) 0.04(2) Uiso 1 1 d . . . H7B H 1.044(9) 0.000(6) 0.094(4) 0.030(19) Uiso 1 1 d . . . C8 C 0.8782(8) 0.0853(5) 0.1218(3) 0.0241(15) Uani 1 1 d . . . C9 C 0.7535(9) 0.0415(6) 0.0476(4) 0.0275(16) Uani 1 1 d . . . H9A H 0.657(13) 0.080(8) 0.041(5) 0.07(3) Uiso 1 1 d . . . H9B H 0.819(10) 0.056(7) 0.005(5) 0.05(2) Uiso 1 1 d . . . C10 C 0.6608(8) -0.0792(6) 0.0334(4) 0.0292(16) Uani 1 1 d . . . H10A H 0.686(11) -0.115(8) -0.010(5) 0.06(3) Uiso 1 1 d . . . C11 C 0.5550(9) -0.1245(6) 0.0713(4) 0.0356(18) Uani 1 1 d . . . H11A H 0.490(8) -0.205(6) 0.053(3) 0.018(16) Uiso 1 1 d . . . C12 C 0.5143(9) -0.0608(7) 0.1383(5) 0.0391(19) Uani 1 1 d . . . H12A H 0.434(9) -0.110(6) 0.158(3) 0.022(17) Uiso 1 1 d . . . H12B H 0.468(9) -0.002(6) 0.117(4) 0.034(19) Uiso 1 1 d . . . C13 C 0.6661(10) -0.0016(7) 0.1984(4) 0.0364(18) Uani 1 1 d . . . H13A H 0.735(9) -0.051(6) 0.210(4) 0.028(18) Uiso 1 1 d . . . H13B H 0.616(9) 0.025(6) 0.243(4) 0.029(18) Uiso 1 1 d . . . C14 C 0.7836(9) 0.1012(6) 0.1855(4) 0.0276(16) Uani 1 1 d . . . H14A H 0.874(8) 0.129(5) 0.238(4) 0.022(16) Uiso 1 1 d . . . C15 C 0.7057(8) 0.2738(5) 0.2199(4) 0.0271(16) Uani 1 1 d . . . C16 C 0.6112(8) 0.3517(5) 0.1918(3) 0.0221(14) Uani 1 1 d . . . C17 C 0.5570(8) 0.3446(6) 0.1178(4) 0.0300(17) Uani 1 1 d . . . H17A H 0.575(8) 0.285(6) 0.092(4) 0.023(18) Uiso 1 1 d . . . C18 C 0.4796(9) 0.4246(6) 0.0939(4) 0.0294(16) Uani 1 1 d . . . H18A H 0.451(10) 0.423(7) 0.044(5) 0.05(2) Uiso 1 1 d . . . C19 C 0.4601(8) 0.5089(5) 0.1455(4) 0.0278(16) Uani 1 1 d . . . C20 C 0.5109(9) 0.5164(6) 0.2199(4) 0.0308(17) Uani 1 1 d . . . H20A H 0.492(9) 0.581(6) 0.242(4) 0.03(2) Uiso 1 1 d . . . C21 C 0.5887(8) 0.4379(6) 0.2429(4) 0.0307(16) Uani 1 1 d . . . H21A H 0.629(7) 0.435(5) 0.295(4) 0.014(15) Uiso 1 1 d . . . O31 O 0.6324(5) 0.7495(4) 0.3692(2) 0.0299(12) Uani 1 1 d . . . O32 O 0.9031(6) 0.8477(4) 0.4171(3) 0.0353(12) Uani 1 1 d . . . O33 O 0.4233(5) 0.6988(4) 0.4553(2) 0.0277(11) Uani 1 1 d . . . O34 O 0.4069(6) 0.5188(4) 0.4071(3) 0.0377(13) Uani 1 1 d . . . O35 O -0.1418(8) 0.7344(5) 0.1621(3) 0.0515(15) Uani 1 1 d . . . O36 O -0.1421(8) 0.5684(5) 0.1084(3) 0.0524(16) Uani 1 1 d . . . N31 N -0.0946(8) 0.6475(5) 0.1600(3) 0.0362(15) Uani 1 1 d . . . C31 C 0.6974(11) 0.7991(9) 0.3139(5) 0.047(2) Uani 1 1 d . . . H31A H 0.628(11) 0.836(7) 0.297(5) 0.04(3) Uiso 1 1 d . . . H31B H 0.730(11) 0.744(8) 0.285(5) 0.05(3) Uiso 1 1 d . . . C32 C 0.8412(10) 0.8937(7) 0.3566(5) 0.043(2) Uani 1 1 d . . . H32A H 0.915(11) 0.907(7) 0.323(5) 0.05(3) Uiso 1 1 d . . . H32B H 0.809(18) 0.981(12) 0.362(8) 0.14(5) Uiso 1 1 d . . . C33 C 0.7708(8) 0.7603(5) 0.4276(3) 0.0255(15) Uani 1 1 d . . . C34 C 0.8322(9) 0.6538(6) 0.4199(4) 0.0313(17) Uani 1 1 d . . . H34A H 0.864(8) 0.641(5) 0.369(4) 0.021(16) Uiso 1 1 d . . . H34B H 0.736(11) 0.587(7) 0.415(4) 0.05(2) Uiso 1 1 d . . . C35 C 0.9828(10) 0.6627(7) 0.4808(4) 0.0390(19) Uani 1 1 d . . . H35A H 1.005(15) 0.583(10) 0.486(7) 0.11(4) Uiso 1 1 d . . . H35B H 1.071(11) 0.722(7) 0.469(5) 0.05(2) Uiso 1 1 d . . . C36 C 0.9385(11) 0.6928(8) 0.5550(4) 0.041(2) Uani 1 1 d . . . H36A H 1.028(11) 0.707(6) 0.589(4) 0.04(2) Uiso 1 1 d . . . H36B H 0.853(8) 0.631(5) 0.560(3) 0.012(15) Uiso 1 1 d . . . C37 C 0.8773(9) 0.7980(7) 0.5613(4) 0.0328(17) Uani 1 1 d . . . H37A H 0.965(12) 0.858(7) 0.559(4) 0.05(2) Uiso 1 1 d . . . H37B H 0.858(9) 0.824(6) 0.602(4) 0.03(2) Uiso 1 1 d . . . C38 C 0.7204(8) 0.7945(6) 0.5024(4) 0.0277(16) Uani 1 1 d . . . C39 C 0.6852(10) 0.9110(6) 0.5077(4) 0.0355(18) Uani 1 1 d . . . H39A H 0.819(12) 0.964(8) 0.481(5) 0.07(3) Uiso 1 1 d . . . H39B H 0.580(9) 0.909(5) 0.473(3) 0.019(16) Uiso 1 1 d . . . C40 C 0.6842(10) 0.9705(7) 0.5830(4) 0.041(2) Uani 1 1 d . . . H40A H 0.765(10) 1.056(7) 0.590(4) 0.04(2) Uiso 1 1 d . . . C41 C 0.5728(10) 0.9363(7) 0.6229(4) 0.044(2) Uani 1 1 d . . . H41A H 0.615(11) 0.980(7) 0.682(5) 0.06(2) Uiso 1 1 d . . . C42 C 0.4423(10) 0.8288(8) 0.6006(5) 0.041(2) Uani 1 1 d . . . H42A H 0.359(12) 0.846(7) 0.563(5) 0.06(3) Uiso 1 1 d . . . H42B H 0.393(8) 0.820(5) 0.632(4) 0.016(18) Uiso 1 1 d . . . C43 C 0.5066(10) 0.7250(7) 0.5839(4) 0.0386(19) Uani 1 1 d . . . H43A H 0.429(8) 0.657(5) 0.587(3) 0.011(15) Uiso 1 1 d . . . H43B H 0.626(8) 0.720(5) 0.625(3) 0.021(16) Uiso 1 1 d . . . C44 C 0.5678(9) 0.7049(6) 0.5132(3) 0.0278(16) Uani 1 1 d . . . H44A H 0.589(7) 0.632(5) 0.505(3) 0.014(15) Uiso 1 1 d . . . C45 C 0.3651(8) 0.6048(5) 0.4056(4) 0.0269(16) Uani 1 1 d . . . C46 C 0.2414(8) 0.6187(5) 0.3434(4) 0.0250(15) Uani 1 1 d . . . C47 C 0.1402(8) 0.5247(6) 0.2955(4) 0.0265(16) Uani 1 1 d . . . H47A H 0.146(8) 0.456(6) 0.303(3) 0.016(16) Uiso 1 1 d . . . C48 C 0.0304(9) 0.5322(6) 0.2350(4) 0.0295(16) Uani 1 1 d . . . H48A H -0.035(9) 0.469(6) 0.200(4) 0.033(19) Uiso 1 1 d . . . C49 C 0.0222(8) 0.6384(6) 0.2247(4) 0.0272(15) Uani 1 1 d . . . C50 C 0.1187(9) 0.7336(6) 0.2714(4) 0.0312(17) Uani 1 1 d . . . H50A H 0.115(9) 0.812(6) 0.265(4) 0.033(19) Uiso 1 1 d . . . C51 C 0.2292(9) 0.7246(6) 0.3313(4) 0.0318(17) Uani 1 1 d . . . H51A H 0.309(8) 0.790(5) 0.359(3) 0.017(16) 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 O1 0.028(3) 0.035(3) 0.033(3) 0.010(2) 0.013(2) 0.009(2) O2 0.028(3) 0.021(2) 0.035(3) 0.008(2) 0.005(2) 0.009(2) O3 0.028(3) 0.022(2) 0.025(2) 0.0028(19) 0.0019(19) 0.009(2) O4 0.048(3) 0.034(3) 0.028(3) 0.002(2) -0.007(3) 0.014(2) O5 0.063(4) 0.052(4) 0.049(4) 0.014(3) -0.006(3) 0.026(3) O6 0.064(4) 0.034(3) 0.068(4) 0.006(3) 0.028(3) 0.025(3) N1 0.026(3) 0.033(4) 0.056(5) 0.018(3) 0.010(3) 0.007(3) C1 0.038(5) 0.042(5) 0.035(4) 0.021(4) 0.011(4) 0.009(4) C2 0.031(4) 0.028(4) 0.054(5) 0.021(4) 0.009(4) 0.006(4) C3 0.022(3) 0.023(4) 0.026(3) 0.003(3) 0.003(3) 0.005(3) C4 0.024(4) 0.031(4) 0.030(4) 0.007(3) 0.003(3) 0.004(3) C5 0.021(4) 0.039(4) 0.034(4) 0.008(3) -0.003(3) 0.004(3) C6 0.025(4) 0.032(4) 0.030(4) 0.008(3) 0.000(3) 0.010(3) C7 0.027(4) 0.019(4) 0.036(4) 0.005(3) 0.003(3) 0.004(3) C8 0.024(3) 0.026(4) 0.023(3) 0.004(3) 0.003(3) 0.009(3) C9 0.023(4) 0.032(4) 0.024(4) 0.003(3) 0.001(3) 0.006(3) C10 0.022(4) 0.036(4) 0.027(4) 0.005(3) 0.001(3) 0.007(3) C11 0.025(4) 0.026(4) 0.049(5) 0.003(3) -0.004(3) 0.003(3) C12 0.025(4) 0.029(4) 0.065(5) 0.012(4) 0.016(4) 0.003(3) C13 0.040(4) 0.034(4) 0.039(4) 0.010(4) 0.012(4) 0.012(4) C14 0.028(4) 0.026(4) 0.030(4) 0.005(3) 0.008(3) 0.010(3) C15 0.027(4) 0.024(4) 0.033(4) 0.004(3) 0.010(3) 0.009(3) C16 0.016(3) 0.018(3) 0.029(4) 0.004(3) 0.003(3) -0.002(3) C17 0.025(4) 0.027(4) 0.037(4) -0.002(3) 0.005(3) 0.010(3) C18 0.026(4) 0.031(4) 0.029(4) 0.007(3) 0.002(3) 0.002(3) C19 0.020(3) 0.024(4) 0.039(4) 0.006(3) 0.004(3) 0.004(3) C20 0.029(4) 0.025(4) 0.040(4) 0.001(3) 0.015(3) 0.008(3) C21 0.025(4) 0.036(4) 0.028(4) 0.001(3) 0.003(3) 0.005(3) O31 0.023(2) 0.036(3) 0.028(3) 0.013(2) 0.000(2) 0.000(2) O32 0.026(3) 0.036(3) 0.037(3) 0.005(2) 0.003(2) -0.003(2) O33 0.023(2) 0.026(3) 0.029(3) 0.002(2) -0.002(2) 0.004(2) O34 0.042(3) 0.023(3) 0.039(3) 0.001(2) -0.008(2) 0.004(2) O35 0.066(4) 0.050(4) 0.043(3) 0.015(3) 0.001(3) 0.027(3) O36 0.067(4) 0.041(3) 0.039(3) -0.002(3) -0.010(3) 0.011(3) N31 0.034(3) 0.037(4) 0.037(4) 0.009(3) 0.009(3) 0.006(3) C31 0.037(5) 0.060(6) 0.036(5) 0.023(5) -0.002(4) -0.005(5) C32 0.036(5) 0.048(5) 0.042(5) 0.019(4) 0.003(4) -0.004(4) C33 0.017(3) 0.023(4) 0.028(4) 0.005(3) -0.003(3) -0.009(3) C34 0.028(4) 0.029(4) 0.035(4) 0.006(3) 0.001(3) 0.005(3) C35 0.027(4) 0.046(5) 0.045(5) 0.012(4) 0.003(3) 0.012(4) C36 0.025(4) 0.054(6) 0.036(5) 0.011(4) -0.010(4) 0.004(4) C37 0.025(4) 0.035(5) 0.030(4) -0.003(3) 0.000(3) 0.001(4) C38 0.022(3) 0.029(4) 0.025(4) -0.002(3) -0.002(3) 0.000(3) C39 0.031(4) 0.035(4) 0.033(4) -0.002(3) -0.006(3) 0.007(3) C40 0.029(4) 0.038(5) 0.048(5) -0.005(4) -0.005(4) 0.010(4) C41 0.036(5) 0.054(5) 0.042(5) -0.001(4) 0.005(4) 0.019(4) C42 0.028(4) 0.061(6) 0.030(4) 0.001(4) 0.005(4) 0.010(4) C43 0.039(5) 0.037(5) 0.034(4) 0.002(3) 0.008(4) 0.002(4) C44 0.028(4) 0.029(4) 0.021(3) 0.005(3) -0.006(3) 0.004(3) C45 0.028(4) 0.017(4) 0.034(4) 0.004(3) 0.009(3) 0.000(3) C46 0.021(3) 0.021(4) 0.033(4) 0.005(3) 0.008(3) 0.002(3) C47 0.026(4) 0.020(4) 0.033(4) 0.006(3) -0.001(3) 0.006(3) C48 0.024(4) 0.027(4) 0.030(4) 0.002(3) 0.002(3) -0.005(3) C49 0.025(4) 0.028(4) 0.028(4) 0.009(3) 0.005(3) 0.006(3) C50 0.036(4) 0.021(4) 0.037(4) 0.009(3) 0.008(3) 0.005(3) C51 0.030(4) 0.028(4) 0.029(4) -0.004(3) 0.001(3) 0.000(3) _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 C3 1.437(8) . ? O1 C1 1.454(9) . ? O2 C2 1.425(9) . ? O2 C3 1.440(8) . ? O3 C15 1.347(8) . ? O3 C14 1.475(8) . ? O4 C15 1.202(8) . ? O5 N1 1.226(8) . ? O6 N1 1.230(8) . ? N1 C19 1.481(9) . ? C1 C2 1.487(11) . ? C3 C4 1.523(9) . ? C3 C8 1.559(9) . ? C4 C5 1.530(10) . ? C5 C6 1.530(10) . ? C6 C7 1.543(10) . ? C7 C8 1.542(9) . ? C8 C14 1.551(9) . ? C8 C9 1.553(9) . ? C9 C10 1.504(10) . ? C10 C11 1.313(10) . ? C11 C12 1.515(11) . ? C12 C13 1.525(11) . ? C13 C14 1.519(10) . ? C15 C16 1.491(9) . ? C16 C17 1.387(10) . ? C16 C21 1.398(9) . ? C17 C18 1.399(10) . ? C18 C19 1.377(10) . ? C19 C20 1.390(10) . ? C20 C21 1.378(10) . ? O31 C31 1.420(9) . ? O31 C33 1.434(8) . ? O32 C32 1.436(9) . ? O32 C33 1.438(8) . ? O33 C45 1.332(8) . ? O33 C44 1.476(8) . ? O34 C45 1.205(8) . ? O35 N31 1.233(8) . ? O36 N31 1.225(8) . ? N31 C49 1.478(9) . ? C31 C32 1.510(12) . ? C33 C34 1.524(10) . ? C33 C38 1.563(9) . ? C34 C35 1.537(10) . ? C35 C36 1.521(12) . ? C36 C37 1.508(12) . ? C37 C38 1.568(10) . ? C38 C39 1.542(10) . ? C38 C44 1.567(10) . ? C39 C40 1.505(11) . ? C40 C41 1.329(12) . ? C41 C42 1.491(12) . ? C42 C43 1.519(12) . ? C43 C44 1.510(10) . ? C45 C46 1.498(10) . ? C46 C47 1.386(9) . ? C46 C51 1.404(10) . ? C47 C48 1.380(10) . ? C48 C49 1.390(10) . ? C49 C50 1.374(10) . ? C50 C51 1.381(10) . ? 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 C3 O1 C1 108.3(5) . . ? C2 O2 C3 107.2(5) . . ? C15 O3 C14 117.5(5) . . ? O5 N1 O6 124.1(6) . . ? O5 N1 C19 118.2(6) . . ? O6 N1 C19 117.7(6) . . ? O1 C1 C2 103.1(6) . . ? O2 C2 C1 102.6(6) . . ? O1 C3 O2 105.3(5) . . ? O1 C3 C4 107.8(5) . . ? O2 C3 C4 110.2(5) . . ? O1 C3 C8 109.1(5) . . ? O2 C3 C8 111.2(5) . . ? C4 C3 C8 112.9(5) . . ? C3 C4 C5 111.5(6) . . ? C6 C5 C4 110.6(6) . . ? C5 C6 C7 110.0(6) . . ? C8 C7 C6 114.4(6) . . ? C7 C8 C14 109.9(5) . . ? C7 C8 C9 109.5(5) . . ? C14 C8 C9 111.1(5) . . ? C7 C8 C3 105.8(5) . . ? C14 C8 C3 110.8(5) . . ? C9 C8 C3 109.5(5) . . ? C10 C9 C8 115.6(6) . . ? C11 C10 C9 125.9(7) . . ? C10 C11 C12 123.7(7) . . ? C11 C12 C13 114.8(6) . . ? C14 C13 C12 117.7(7) . . ? O3 C14 C13 105.8(5) . . ? O3 C14 C8 107.8(5) . . ? C13 C14 C8 117.3(6) . . ? O4 C15 O3 124.4(6) . . ? O4 C15 C16 124.3(6) . . ? O3 C15 C16 111.3(6) . . ? C17 C16 C21 120.7(6) . . ? C17 C16 C15 121.9(6) . . ? C21 C16 C15 117.3(6) . . ? C16 C17 C18 119.7(7) . . ? C19 C18 C17 118.3(7) . . ? C18 C19 C20 122.9(7) . . ? C18 C19 N1 118.1(6) . . ? C20 C19 N1 119.0(6) . . ? C21 C20 C19 118.4(7) . . ? C20 C21 C16 120.0(7) . . ? C31 O31 C33 107.5(5) . . ? C32 O32 C33 109.1(5) . . ? C45 O33 C44 117.9(5) . . ? O36 N31 O35 123.8(6) . . ? O36 N31 C49 118.9(6) . . ? O35 N31 C49 117.2(6) . . ? O31 C31 C32 103.0(6) . . ? O32 C32 C31 102.2(6) . . ? O31 C33 O32 105.5(5) . . ? O31 C33 C34 109.7(5) . . ? O32 C33 C34 107.3(5) . . ? O31 C33 C38 109.9(5) . . ? O32 C33 C38 109.9(5) . . ? C34 C33 C38 114.2(6) . . ? C33 C34 C35 111.3(6) . . ? C36 C35 C34 110.3(6) . . ? C37 C36 C35 111.0(7) . . ? C36 C37 C38 115.2(6) . . ? C39 C38 C33 109.2(6) . . ? C39 C38 C44 112.3(6) . . ? C33 C38 C44 111.3(5) . . ? C39 C38 C37 110.3(6) . . ? C33 C38 C37 105.1(6) . . ? C44 C38 C37 108.4(6) . . ? C40 C39 C38 115.9(6) . . ? C41 C40 C39 124.4(7) . . ? C40 C41 C42 123.5(8) . . ? C41 C42 C43 115.8(7) . . ? C44 C43 C42 117.1(7) . . ? O33 C44 C43 105.6(6) . . ? O33 C44 C38 107.8(5) . . ? C43 C44 C38 117.6(6) . . ? O34 C45 O33 126.4(6) . . ? O34 C45 C46 122.2(6) . . ? O33 C45 C46 111.4(6) . . ? C47 C46 C51 119.4(6) . . ? C47 C46 C45 119.0(6) . . ? C51 C46 C45 121.6(6) . . ? C48 C47 C46 121.7(7) . . ? C47 C48 C49 117.2(6) . . ? C50 C49 C48 122.9(6) . . ? C50 C49 N31 119.4(6) . . ? C48 C49 N31 117.7(6) . . ? C49 C50 C51 119.1(7) . . ? C50 C51 C46 119.6(6) . . ? _diffrn_measured_fraction_theta_max 0.996 _diffrn_reflns_theta_full 23.25 _diffrn_measured_fraction_theta_full 0.996 _refine_diff_density_max 0.653 _refine_diff_density_min -0.400 _refine_diff_density_rms 0.108