data_mis263 _audit_creation_method SHELXL-97 _chemical_name_systematic ; methyl-5-isopropenyl-2-methyl-6-oxo-1,4,5,6-tetrahydrocyclopenta[b]pyrrole-3-carboxylate ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C26 H30 N2 O6' _chemical_formula_weight 466.52 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source 'C' 'C' 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 'H' 'H' 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 'N' 'N' 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 'O' 'O' 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting triclinic _symmetry_space_group_name_H-M ? loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 5.160(2) _cell_length_b 10.5619(7) _cell_length_c 11.939(2) _cell_angle_alpha 108.097(8) _cell_angle_beta 99.00(3) _cell_angle_gamma 94.537(17) _cell_volume 605.2(3) _cell_formula_units_Z 1 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used 25 _cell_measurement_theta_min 22.24 _cell_measurement_theta_max 32.84 _exptl_crystal_description blade _exptl_crystal_colour colourless _exptl_crystal_size_max 0.34 _exptl_crystal_size_mid 0.17 _exptl_crystal_size_min 0.07 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.280 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 248 _exptl_absorpt_coefficient_mu 0.748 _exptl_absorpt_correction_type 'psi-scan' _exptl_absorpt_correction_T_min 0.8993 _exptl_absorpt_correction_T_max 0.9901 _exptl_absorpt_process_details ; North, A.C., Phillips, D.C. & Mattews, F.S. (1968). Acta Cryst., A24, 351-359. ; _exptl_special_details ; ? ; _diffrn_ambient_temperature 293(2) _diffrn_radiation_wavelength 1.5418 _diffrn_radiation_type CuK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'CAD4-Enraf-Nonius' _diffrn_measurement_method '\w-2\q scans' _diffrn_standards_number 3 _diffrn_standards_interval_count ? _diffrn_standards_interval_time 180 _diffrn_standards_decay_% 3 _diffrn_reflns_number 4673 _diffrn_reflns_av_R_equivalents 0.0281 _diffrn_reflns_av_sigmaI/netI 0.0295 _diffrn_reflns_limit_h_min -6 _diffrn_reflns_limit_h_max 6 _diffrn_reflns_limit_k_min -13 _diffrn_reflns_limit_k_max 13 _diffrn_reflns_limit_l_min -14 _diffrn_reflns_limit_l_max 14 _diffrn_reflns_theta_min 3.97 _diffrn_reflns_theta_max 72.72 _reflns_number_total 2406 _reflns_number_gt 1880 _reflns_threshold_expression I>2\s(I) _computing_data_collection 'CAD-4 software (Enraf-Nonius, 1989)' _computing_cell_refinement 'CAD-4 software (Enraf-Nonius, 1989)' _computing_data_reduction 'HELENA (Spek, 1997)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'ORTEPII (Johnson, 1976)' _computing_publication_material 'SHELXL-97 (Sheldrick, 1997)' _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^)+(0.0697P)^2^+0.1228P] 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 0.0106(19) _refine_ls_extinction_expression 'Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^' _refine_ls_number_reflns 2406 _refine_ls_number_parameters 158 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0600 _refine_ls_R_factor_gt 0.0445 _refine_ls_wR_factor_ref 0.1308 _refine_ls_wR_factor_gt 0.1188 _refine_ls_goodness_of_fit_ref 1.053 _refine_ls_restrained_S_all 1.053 _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 O3 O 1.1514(2) 0.22091(12) 0.08562(12) 0.0559(3) Uani 1 1 d . . . O1 O 0.2236(3) -0.05314(13) 0.34543(14) 0.0669(4) Uani 1 1 d . . . O2 O 0.3584(2) 0.16810(12) 0.42955(11) 0.0521(3) Uani 1 1 d . . . N1 N 0.7438(3) -0.01312(13) 0.11141(12) 0.0452(3) Uani 1 1 d . . . H1 H 0.7977 -0.0625 0.0498 0.054 Uiso 1 1 calc R . . C2 C 0.5656(3) -0.05534(16) 0.16813(15) 0.0445(4) Uani 1 1 d . . . C3 C 0.5281(3) 0.05544(16) 0.26364(15) 0.0435(4) Uani 1 1 d . . . C3A C 0.6946(3) 0.16673(16) 0.26170(15) 0.0424(4) Uani 1 1 d . . . C4 C 0.7727(3) 0.31389(16) 0.32532(17) 0.0505(4) Uani 1 1 d . . . H4A H 0.8207 0.3332 0.4114 0.061 Uiso 1 1 calc R . . H4B H 0.6304 0.3641 0.3087 0.061 Uiso 1 1 calc R . . C5 C 1.0160(3) 0.34805(16) 0.27242(16) 0.0476(4) Uani 1 1 d . . . H5 H 1.1744 0.3506 0.3307 0.057 Uiso 1 1 calc R . . C6 C 1.0106(3) 0.22481(16) 0.16016(15) 0.0447(4) Uani 1 1 d . . . C6A C 0.8250(3) 0.12201(15) 0.16856(15) 0.0428(4) Uani 1 1 d . . . C7 C 0.4459(4) -0.19817(18) 0.12796(18) 0.0603(5) Uani 1 1 d . . . H7A H 0.5087 -0.2475 0.0577 0.090 Uiso 1 1 calc R . . H7B H 0.2565 -0.2039 0.1095 0.090 Uiso 1 1 calc R . . H7C H 0.4948 -0.2355 0.1907 0.090 Uiso 1 1 calc R . . C8 C 0.3543(3) 0.04739(17) 0.34737(16) 0.0461(4) Uani 1 1 d . . . C9 C 0.1989(4) 0.1698(2) 0.51925(18) 0.0605(5) Uani 1 1 d . . . H9A H 0.0180 0.1362 0.4805 0.091 Uiso 1 1 calc R . . H9B H 0.2096 0.2603 0.5722 0.091 Uiso 1 1 calc R . . H9C H 0.2634 0.1141 0.5645 0.091 Uiso 1 1 calc R . . C10 C 1.0335(4) 0.48102(17) 0.25283(17) 0.0541(5) Uani 1 1 d . . . C11 C 1.2139(5) 0.5824(2) 0.3246(2) 0.0757(7) Uani 1 1 d . . . H11A H 1.3298 0.5705 0.3874 0.091 Uiso 1 1 calc R . . H11B H 1.2241 0.6651 0.3121 0.091 Uiso 1 1 calc R . . C12 C 0.8373(6) 0.4956(3) 0.1531(3) 0.0883(8) Uani 1 1 d . . . H12A H 0.8501 0.5883 0.1576 0.132 Uiso 1 1 calc R . . H12B H 0.6618 0.4656 0.1601 0.132 Uiso 1 1 calc R . . H12C H 0.8737 0.4423 0.0775 0.132 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 O3 0.0622(7) 0.0512(7) 0.0599(8) 0.0142(6) 0.0373(6) 0.0067(5) O1 0.0754(9) 0.0526(7) 0.0797(9) 0.0205(7) 0.0430(7) -0.0021(6) O2 0.0555(7) 0.0536(7) 0.0511(7) 0.0147(5) 0.0284(6) 0.0029(5) N1 0.0499(7) 0.0430(7) 0.0436(7) 0.0106(6) 0.0200(6) 0.0054(5) C2 0.0443(8) 0.0461(8) 0.0453(9) 0.0160(7) 0.0144(7) 0.0038(6) C3 0.0428(8) 0.0460(8) 0.0453(9) 0.0163(7) 0.0171(7) 0.0045(6) C3A 0.0423(7) 0.0439(8) 0.0443(8) 0.0141(7) 0.0178(6) 0.0074(6) C4 0.0546(9) 0.0440(8) 0.0566(10) 0.0124(8) 0.0304(8) 0.0054(7) C5 0.0463(8) 0.0470(9) 0.0500(9) 0.0112(7) 0.0218(7) 0.0033(7) C6 0.0441(8) 0.0459(8) 0.0486(9) 0.0148(7) 0.0219(7) 0.0095(6) C6A 0.0440(8) 0.0415(8) 0.0448(8) 0.0118(7) 0.0190(7) 0.0067(6) C7 0.0726(12) 0.0476(10) 0.0588(11) 0.0124(8) 0.0235(9) -0.0026(8) C8 0.0444(8) 0.0501(9) 0.0488(9) 0.0189(7) 0.0183(7) 0.0053(7) C9 0.0610(10) 0.0716(12) 0.0545(10) 0.0188(9) 0.0319(9) 0.0081(9) C10 0.0609(10) 0.0451(9) 0.0594(10) 0.0111(8) 0.0336(9) 0.0059(7) C11 0.0859(14) 0.0534(11) 0.0830(15) 0.0065(10) 0.0435(12) -0.0080(10) C12 0.110(2) 0.0695(14) 0.0965(19) 0.0374(14) 0.0250(16) 0.0234(14) _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 C6 1.2271(19) . ? O1 C8 1.204(2) . ? O2 C8 1.342(2) . ? O2 C9 1.446(2) . ? N1 C2 1.350(2) . ? N1 C6A 1.374(2) . ? N1 H1 0.8600 . ? C2 C3 1.408(2) . ? C2 C7 1.482(2) . ? C3 C3A 1.408(2) . ? C3 C8 1.460(2) . ? C3A C6A 1.368(2) . ? C3A C4 1.492(2) . ? C4 C5 1.557(2) . ? C4 H4A 0.9700 . ? C4 H4B 0.9700 . ? C5 C10 1.492(2) . ? C5 C6 1.546(2) . ? C5 H5 0.9800 . ? C6 C6A 1.428(2) . ? C7 H7A 0.9600 . ? C7 H7B 0.9600 . ? C7 H7C 0.9600 . ? C9 H9A 0.9600 . ? C9 H9B 0.9600 . ? C9 H9C 0.9600 . ? C10 C11 1.330(3) . ? C10 C12 1.492(3) . ? C11 H11A 0.9300 . ? C11 H11B 0.9300 . ? C12 H12A 0.9600 . ? C12 H12B 0.9600 . ? C12 H12C 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 C8 O2 C9 115.41(14) . . ? C2 N1 C6A 108.64(13) . . ? C2 N1 H1 125.7 . . ? C6A N1 H1 125.7 . . ? N1 C2 C3 108.51(14) . . ? N1 C2 C7 121.05(15) . . ? C3 C2 C7 130.44(15) . . ? C2 C3 C3A 106.37(14) . . ? C2 C3 C8 124.10(15) . . ? C3A C3 C8 129.49(15) . . ? C6A C3A C3 107.30(14) . . ? C6A C3A C4 111.16(13) . . ? C3 C3A C4 141.53(14) . . ? C3A C4 C5 103.23(12) . . ? C3A C4 H4A 111.1 . . ? C5 C4 H4A 111.1 . . ? C3A C4 H4B 111.1 . . ? C5 C4 H4B 111.1 . . ? H4A C4 H4B 109.1 . . ? C10 C5 C6 115.60(15) . . ? C10 C5 C4 115.02(14) . . ? C6 C5 C4 105.12(13) . . ? C10 C5 H5 106.8 . . ? C6 C5 H5 106.8 . . ? C4 C5 H5 106.8 . . ? O3 C6 C6A 129.93(15) . . ? O3 C6 C5 124.43(15) . . ? C6A C6 C5 105.56(13) . . ? C3A C6A N1 109.17(14) . . ? C3A C6A C6 112.87(14) . . ? N1 C6A C6 137.91(14) . . ? C2 C7 H7A 109.5 . . ? C2 C7 H7B 109.5 . . ? H7A C7 H7B 109.5 . . ? C2 C7 H7C 109.5 . . ? H7A C7 H7C 109.5 . . ? H7B C7 H7C 109.5 . . ? O1 C8 O2 123.20(15) . . ? O1 C8 C3 125.61(16) . . ? O2 C8 C3 111.19(14) . . ? O2 C9 H9A 109.5 . . ? O2 C9 H9B 109.5 . . ? H9A C9 H9B 109.5 . . ? O2 C9 H9C 109.5 . . ? H9A C9 H9C 109.5 . . ? H9B C9 H9C 109.5 . . ? C11 C10 C5 120.3(2) . . ? C11 C10 C12 122.3(2) . . ? C5 C10 C12 117.41(17) . . ? C10 C11 H11A 120.0 . . ? C10 C11 H11B 120.0 . . ? H11A C11 H11B 120.0 . . ? C10 C12 H12A 109.5 . . ? C10 C12 H12B 109.5 . . ? H12A C12 H12B 109.5 . . ? C10 C12 H12C 109.5 . . ? H12A C12 H12C 109.5 . . ? H12B C12 H12C 109.5 . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag C6A N1 C2 C3 0.64(19) . . . . ? C6A N1 C2 C7 -178.82(16) . . . . ? N1 C2 C3 C3A -0.27(19) . . . . ? C7 C2 C3 C3A 179.13(18) . . . . ? N1 C2 C3 C8 -178.20(15) . . . . ? C7 C2 C3 C8 1.2(3) . . . . ? C2 C3 C3A C6A -0.21(19) . . . . ? C8 C3 C3A C6A 177.57(17) . . . . ? C2 C3 C3A C4 179.2(2) . . . . ? C8 C3 C3A C4 -3.1(4) . . . . ? C6A C3A C4 C5 -11.0(2) . . . . ? C3 C3A C4 C5 169.6(2) . . . . ? C3A C4 C5 C10 142.39(16) . . . . ? C3A C4 C5 C6 14.07(18) . . . . ? C10 C5 C6 O3 42.3(2) . . . . ? C4 C5 C6 O3 170.28(17) . . . . ? C10 C5 C6 C6A -140.71(15) . . . . ? C4 C5 C6 C6A -12.73(18) . . . . ? C3 C3A C6A N1 0.61(19) . . . . ? C4 C3A C6A N1 -178.97(14) . . . . ? C3 C3A C6A C6 -177.30(14) . . . . ? C4 C3A C6A C6 3.1(2) . . . . ? C2 N1 C6A C3A -0.79(19) . . . . ? C2 N1 C6A C6 176.3(2) . . . . ? O3 C6 C6A C3A -176.84(18) . . . . ? C5 C6 C6A C3A 6.40(19) . . . . ? O3 C6 C6A N1 6.1(3) . . . . ? C5 C6 C6A N1 -170.7(2) . . . . ? C9 O2 C8 O1 1.6(3) . . . . ? C9 O2 C8 C3 -178.02(14) . . . . ? C2 C3 C8 O1 0.0(3) . . . . ? C3A C3 C8 O1 -177.40(18) . . . . ? C2 C3 C8 O2 179.61(15) . . . . ? C3A C3 C8 O2 2.2(3) . . . . ? C6 C5 C10 C11 -130.04(18) . . . . ? C4 C5 C10 C11 107.1(2) . . . . ? C6 C5 C10 C12 51.8(2) . . . . ? C4 C5 C10 C12 -71.1(2) . . . . ? loop_ _geom_hbond_atom_site_label_D _geom_hbond_atom_site_label_H _geom_hbond_atom_site_label_A _geom_hbond_distance_DH _geom_hbond_distance_HA _geom_hbond_distance_DA _geom_hbond_angle_DHA _geom_hbond_site_symmetry_A N1 H1 O3 0.86 2.00 2.8321(18) 162.3 2_755 _diffrn_measured_fraction_theta_max 0.998 _diffrn_reflns_theta_full 72.72 _diffrn_measured_fraction_theta_full 0.998 _refine_diff_density_max 0.235 _refine_diff_density_min -0.173 _refine_diff_density_rms 0.053