Supplementary Material (ESI) for Organic & Biomolecular Chemistry This journal is (c) The Royal Society of Chemistry 2007 data_global _journal_coden_Cambridge 177 loop_ _publ_author_name 'Jonathan M. White' 'Yit Wooi Goh' _publ_contact_author_name 'Jonathan M. White' _publ_contact_author_address ; University of Melbourne Room: 551, Bio21 Institute Parkville VIC 3010 Melbourne 3010 AUSTRALIA ; _publ_contact_author_email WHITEJM@UNIMELB.EDU.AU _publ_requested_journal 'Organic & Biomolecular Chemistry' _publ_section_title ; Structures of Oxygenated Cyclohexa-1,3-diene - Maleic anyhydride Cycloadducts. First Structural evidence for a Stepwise Retro Diels Alder Reaction ; data_jmwrg122 _database_code_depnum_ccdc_archive 'CCDC 647990' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C11 H12 O4' _chemical_formula_weight 208.21 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' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Monoclinic _symmetry_space_group_name_H-M '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 6.9224(7) _cell_length_b 13.7063(14) _cell_length_c 10.2746(10) _cell_angle_alpha 90.00 _cell_angle_beta 99.149(2) _cell_angle_gamma 90.00 _cell_volume 962.46(17) _cell_formula_units_Z 4 _cell_measurement_temperature 130(2) _cell_measurement_reflns_used 1848 _cell_measurement_theta_min 2.97 _cell_measurement_theta_max 26.92 _exptl_crystal_description block _exptl_crystal_colour colourless _exptl_crystal_size_min 0.30 _exptl_crystal_size_mid 0.40 _exptl_crystal_size_max 0.40 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.437 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 440 _exptl_absorpt_coefficient_mu 0.110 _exptl_absorpt_correction_type none _exptl_absorpt_correction_T_min ? _exptl_absorpt_correction_T_max ? _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 130(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 '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 4983 _diffrn_reflns_av_R_equivalents 0.0394 _diffrn_reflns_av_sigmaI/netI 0.0410 _diffrn_reflns_limit_h_min -8 _diffrn_reflns_limit_h_max 6 _diffrn_reflns_limit_k_min -16 _diffrn_reflns_limit_k_max 16 _diffrn_reflns_limit_l_min -10 _diffrn_reflns_limit_l_max 12 _diffrn_reflns_theta_min 2.50 _diffrn_reflns_theta_max 25.00 _reflns_number_total 1699 _reflns_number_gt 1398 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'Bruker SMART' _computing_data_reduction 'Bruker SAINT' _computing_structure_solution 'Bruker SHELXTL' _computing_structure_refinement 'Bruker SHELXTL' _computing_molecular_graphics 'Bruker SHELXTL' _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^)+(0.0544P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment mixed _refine_ls_extinction_method SHELXL _refine_ls_extinction_coef 0.008(3) _refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^ _refine_ls_number_reflns 1699 _refine_ls_number_parameters 138 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0449 _refine_ls_R_factor_gt 0.0364 _refine_ls_wR_factor_ref 0.0936 _refine_ls_wR_factor_gt 0.0905 _refine_ls_goodness_of_fit_ref 0.984 _refine_ls_restrained_S_all 0.984 _refine_ls_shift/su_max 0.012 _refine_ls_shift/su_mean 0.003 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group C1 C 0.7023(2) 0.27517(11) 0.27034(15) 0.0249(4) Uani 1 1 d . . . C2 C 0.8128(2) 0.18059(10) 0.29543(14) 0.0218(4) Uani 1 1 d . . . H2 H 0.9490 0.1931 0.3416 0.026 Uiso 1 1 calc R . . C3 C 0.8171(2) 0.12108(10) 0.16574(14) 0.0205(4) Uani 1 1 d . . . C4 C 0.6130(2) 0.08957(10) 0.11219(14) 0.0212(4) Uani 1 1 d . . . H4 H 0.5507 0.1068 0.0261 0.025 Uiso 1 1 calc R . . C5 C 0.5250(2) 0.03619(11) 0.19264(15) 0.0242(4) Uani 1 1 d . . . H5 H 0.3973 0.0101 0.1677 0.029 Uiso 1 1 calc R . . C6 C 0.6431(2) 0.02015(11) 0.32643(15) 0.0248(4) Uani 1 1 d . . . H6 H 0.5692 -0.0189 0.3844 0.030 Uiso 1 1 calc R . . C7 C 0.6969(2) 0.12248(11) 0.38481(14) 0.0238(4) Uani 1 1 d . . . H7 H 0.7735 0.1167 0.4756 0.029 Uiso 1 1 calc R . . C8 C 0.5153(2) 0.18208(11) 0.38707(15) 0.0280(4) Uani 1 1 d . . . C9 C 0.9382(2) 0.02845(11) 0.20957(15) 0.0256(4) Uani 1 1 d . . . H9A H 0.9511 -0.0120 0.1316 0.031 Uiso 1 1 calc R . . H9B H 1.0710 0.0473 0.2529 0.031 Uiso 1 1 calc R . . C10 C 0.8350(2) -0.03089(11) 0.30669(16) 0.0279(4) Uani 1 1 d . . . H10A H 0.8059 -0.0974 0.2715 0.033 Uiso 1 1 calc R . . H10B H 0.9224 -0.0367 0.3925 0.033 Uiso 1 1 calc R . . C11 C 1.0909(2) 0.20051(12) 0.09206(16) 0.0328(4) Uani 1 1 d . . . H11A H 1.1251 0.2241 0.1829 0.049 Uiso 1 1 calc R . . H11B H 1.1182 0.2517 0.0308 0.049 Uiso 1 1 calc R . . H11C H 1.1688 0.1425 0.0800 0.049 Uiso 1 1 calc R . . O1 O 0.74295(17) 0.34741(8) 0.21614(11) 0.0342(3) Uani 1 1 d . . . O2 O 0.37146(18) 0.16262(9) 0.43251(11) 0.0401(4) Uani 1 1 d . . . O4 O 0.52705(15) 0.26982(7) 0.32089(10) 0.0284(3) Uani 1 1 d . . . O5 O 0.88845(14) 0.17632(7) 0.06666(10) 0.0251(3) 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 C1 0.0295(9) 0.0231(8) 0.0216(8) -0.0052(7) 0.0024(7) -0.0004(7) C2 0.0235(9) 0.0205(8) 0.0206(8) -0.0012(6) 0.0009(6) 0.0011(6) C3 0.0228(9) 0.0207(8) 0.0184(8) 0.0005(6) 0.0049(6) -0.0002(6) C4 0.0231(8) 0.0197(8) 0.0201(8) -0.0031(6) 0.0019(6) 0.0015(6) C5 0.0232(9) 0.0206(8) 0.0290(9) -0.0024(7) 0.0049(7) -0.0014(7) C6 0.0307(9) 0.0216(8) 0.0239(8) 0.0042(6) 0.0097(7) -0.0001(7) C7 0.0287(9) 0.0251(8) 0.0174(8) 0.0012(6) 0.0035(6) 0.0045(7) C8 0.0367(10) 0.0281(9) 0.0199(8) -0.0025(7) 0.0068(7) 0.0026(7) C9 0.0264(9) 0.0232(8) 0.0279(9) -0.0013(7) 0.0063(7) 0.0043(7) C10 0.0316(10) 0.0216(8) 0.0309(9) 0.0028(7) 0.0064(7) 0.0050(7) C11 0.0250(10) 0.0364(9) 0.0375(10) 0.0075(8) 0.0065(8) -0.0047(7) O1 0.0468(8) 0.0203(6) 0.0361(7) 0.0013(5) 0.0089(6) 0.0001(5) O2 0.0406(8) 0.0441(8) 0.0411(7) 0.0036(6) 0.0237(6) 0.0078(6) O4 0.0324(7) 0.0251(6) 0.0282(6) -0.0021(5) 0.0066(5) 0.0060(5) O5 0.0220(6) 0.0306(6) 0.0234(6) 0.0047(5) 0.0055(5) -0.0024(5) _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 C1 O1 1.1914(18) . ? C1 O4 1.3955(18) . ? C1 C2 1.506(2) . ? C2 C7 1.535(2) . ? C2 C3 1.5666(19) . ? C2 H2 1.0000 . ? C3 O5 1.4189(16) . ? C3 C4 1.496(2) . ? C3 C9 1.548(2) . ? C4 C5 1.323(2) . ? C4 H4 0.9500 . ? C5 C6 1.500(2) . ? C5 H5 0.9500 . ? C6 C10 1.543(2) . ? C6 C7 1.548(2) . ? C6 H6 1.0000 . ? C7 C8 1.503(2) . ? C7 H7 1.0000 . ? C8 O2 1.1949(19) . ? C8 O4 1.3903(18) . ? C9 C10 1.547(2) . ? C9 H9A 0.9900 . ? C9 H9B 0.9900 . ? C10 H10A 0.9900 . ? C10 H10B 0.9900 . ? C11 O5 1.4233(17) . ? C11 H11A 0.9800 . ? C11 H11B 0.9800 . ? C11 H11C 0.9800 . ? 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 O1 C1 O4 120.10(14) . . ? O1 C1 C2 130.08(15) . . ? O4 C1 C2 109.82(13) . . ? C1 C2 C7 104.44(12) . . ? C1 C2 C3 112.35(12) . . ? C7 C2 C3 108.73(11) . . ? C1 C2 H2 110.4 . . ? C7 C2 H2 110.4 . . ? C3 C2 H2 110.4 . . ? O5 C3 C4 107.83(11) . . ? O5 C3 C9 114.34(12) . . ? C4 C3 C9 107.82(12) . . ? O5 C3 C2 112.85(11) . . ? C4 C3 C2 108.58(12) . . ? C9 C3 C2 105.20(11) . . ? C5 C4 C3 115.59(13) . . ? C5 C4 H4 122.2 . . ? C3 C4 H4 122.2 . . ? C4 C5 C6 114.55(13) . . ? C4 C5 H5 122.7 . . ? C6 C5 H5 122.7 . . ? C5 C6 C10 107.54(12) . . ? C5 C6 C7 106.56(12) . . ? C10 C6 C7 107.61(12) . . ? C5 C6 H6 111.6 . . ? C10 C6 H6 111.6 . . ? C7 C6 H6 111.6 . . ? C8 C7 C2 104.21(12) . . ? C8 C7 C6 110.37(13) . . ? C2 C7 C6 110.80(12) . . ? C8 C7 H7 110.4 . . ? C2 C7 H7 110.4 . . ? C6 C7 H7 110.4 . . ? O2 C8 O4 120.10(15) . . ? O2 C8 C7 129.48(15) . . ? O4 C8 C7 110.38(13) . . ? C10 C9 C3 109.54(12) . . ? C10 C9 H9A 109.8 . . ? C3 C9 H9A 109.8 . . ? C10 C9 H9B 109.8 . . ? C3 C9 H9B 109.8 . . ? H9A C9 H9B 108.2 . . ? C6 C10 C9 110.00(12) . . ? C6 C10 H10A 109.7 . . ? C9 C10 H10A 109.7 . . ? C6 C10 H10B 109.7 . . ? C9 C10 H10B 109.7 . . ? H10A C10 H10B 108.2 . . ? O5 C11 H11A 109.5 . . ? O5 C11 H11B 109.5 . . ? H11A C11 H11B 109.5 . . ? O5 C11 H11C 109.5 . . ? H11A C11 H11C 109.5 . . ? H11B C11 H11C 109.5 . . ? C8 O4 C1 110.46(12) . . ? C3 O5 C11 115.95(11) . . ? 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 O1 C1 C2 C7 172.80(15) . . . . ? O4 C1 C2 C7 -7.82(15) . . . . ? O1 C1 C2 C3 -69.5(2) . . . . ? O4 C1 C2 C3 109.85(13) . . . . ? C1 C2 C3 O5 53.72(16) . . . . ? C7 C2 C3 O5 168.81(11) . . . . ? C1 C2 C3 C4 -65.76(15) . . . . ? C7 C2 C3 C4 49.33(15) . . . . ? C1 C2 C3 C9 179.03(12) . . . . ? C7 C2 C3 C9 -65.88(14) . . . . ? O5 C3 C4 C5 179.50(12) . . . . ? C9 C3 C4 C5 55.57(16) . . . . ? C2 C3 C4 C5 -57.92(16) . . . . ? C3 C4 C5 C6 2.50(18) . . . . ? C4 C5 C6 C10 -58.87(16) . . . . ? C4 C5 C6 C7 56.28(16) . . . . ? C1 C2 C7 C8 7.96(15) . . . . ? C3 C2 C7 C8 -112.17(12) . . . . ? C1 C2 C7 C6 126.66(13) . . . . ? C3 C2 C7 C6 6.54(16) . . . . ? C5 C6 C7 C8 56.16(15) . . . . ? C10 C6 C7 C8 171.26(12) . . . . ? C5 C6 C7 C2 -58.74(15) . . . . ? C10 C6 C7 C2 56.35(15) . . . . ? C2 C7 C8 O2 171.90(16) . . . . ? C6 C7 C8 O2 52.9(2) . . . . ? C2 C7 C8 O4 -5.88(15) . . . . ? C6 C7 C8 O4 -124.87(13) . . . . ? O5 C3 C9 C10 -174.26(11) . . . . ? C4 C3 C9 C10 -54.36(15) . . . . ? C2 C3 C9 C10 61.37(15) . . . . ? C5 C6 C10 C9 53.67(16) . . . . ? C7 C6 C10 C9 -60.78(16) . . . . ? C3 C9 C10 C6 1.11(17) . . . . ? O2 C8 O4 C1 -176.91(14) . . . . ? C7 C8 O4 C1 1.10(16) . . . . ? O1 C1 O4 C8 -176.15(13) . . . . ? C2 C1 O4 C8 4.40(16) . . . . ? C4 C3 O5 C11 -171.00(12) . . . . ? C9 C3 O5 C11 -51.11(16) . . . . ? C2 C3 O5 C11 69.08(16) . . . . ? _diffrn_measured_fraction_theta_max 0.999 _diffrn_reflns_theta_full 25.00 _diffrn_measured_fraction_theta_full 0.999 _refine_diff_density_max 0.241 _refine_diff_density_min -0.165 _refine_diff_density_rms 0.038 # Attachment 'CMPD9.cif' data_jmwrg16 _database_code_depnum_ccdc_archive 'CCDC 647991' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C12 H14 O5' _chemical_formula_weight 238.23 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' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Monoclinic _symmetry_space_group_name_H-M '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 7.6323(8) _cell_length_b 8.5174(9) _cell_length_c 17.5020(19) _cell_angle_alpha 90.00 _cell_angle_beta 97.041(2) _cell_angle_gamma 90.00 _cell_volume 1129.2(2) _cell_formula_units_Z 4 _cell_measurement_temperature 130(2) _cell_measurement_reflns_used 1503 _cell_measurement_theta_min 2.35 _cell_measurement_theta_max 26.75 _exptl_crystal_description block _exptl_crystal_colour colorless _exptl_crystal_size_min 0.10 _exptl_crystal_size_mid 0.15 _exptl_crystal_size_max 0.20 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.401 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 504 _exptl_absorpt_coefficient_mu 0.110 _exptl_absorpt_correction_type none _exptl_absorpt_correction_T_min ? _exptl_absorpt_correction_T_max ? _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 293(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 '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 6782 _diffrn_reflns_av_R_equivalents 0.0396 _diffrn_reflns_av_sigmaI/netI 0.0570 _diffrn_reflns_limit_h_min -7 _diffrn_reflns_limit_h_max 9 _diffrn_reflns_limit_k_min -11 _diffrn_reflns_limit_k_max 11 _diffrn_reflns_limit_l_min -22 _diffrn_reflns_limit_l_max 17 _diffrn_reflns_theta_min 2.35 _diffrn_reflns_theta_max 27.52 _reflns_number_total 2556 _reflns_number_gt 1798 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'Bruker SMART' _computing_data_reduction 'Bruker SAINT' _computing_structure_solution 'Bruker SHELXTL' _computing_structure_refinement 'Bruker SHELXTL' _computing_molecular_graphics 'Bruker SHELXTL' _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^)+(0.0457P)^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 2556 _refine_ls_number_parameters 156 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0725 _refine_ls_R_factor_gt 0.0484 _refine_ls_wR_factor_ref 0.1051 _refine_ls_wR_factor_gt 0.0965 _refine_ls_goodness_of_fit_ref 0.959 _refine_ls_restrained_S_all 0.959 _refine_ls_shift/su_max 0.002 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group C1 C 1.0954(2) 0.20955(19) 0.22062(11) 0.0243(4) Uani 1 1 d . . . C2 C 0.9189(2) 0.13241(18) 0.20833(10) 0.0226(4) Uani 1 1 d . . . H2 H 0.9154 0.0435 0.2436 0.027 Uiso 1 1 calc R . . C3 C 0.7633(2) 0.2489(2) 0.21768(9) 0.0231(4) Uani 1 1 d . . . C4 C 0.7542(2) 0.36929(19) 0.15438(10) 0.0239(4) Uani 1 1 d . . . H4 H 0.7639 0.4766 0.1638 0.029 Uiso 1 1 calc R . . C5 C 0.7310(2) 0.3089(2) 0.08370(10) 0.0243(4) Uani 1 1 d . . . C6 C 0.7258(2) 0.13245(19) 0.08029(10) 0.0245(4) Uani 1 1 d . . . H6 H 0.7113 0.0945 0.0270 0.029 Uiso 1 1 calc R . . C7 C 0.8999(2) 0.07414(19) 0.12497(10) 0.0226(4) Uani 1 1 d . . . H7 H 0.9055 -0.0408 0.1236 0.027 Uiso 1 1 calc R . . C8 C 1.0578(2) 0.14439(19) 0.09313(11) 0.0264(4) Uani 1 1 d . . . C9 C 0.5950(2) 0.1470(2) 0.20613(10) 0.0292(4) Uani 1 1 d . . . H9A H 0.4926 0.2109 0.2127 0.035 Uiso 1 1 calc R . . H9B H 0.6031 0.0637 0.2442 0.035 Uiso 1 1 calc R . . C10 C 0.5747(2) 0.0755(2) 0.12422(10) 0.0294(4) Uani 1 1 d . . . H10A H 0.5769 -0.0381 0.1276 0.035 Uiso 1 1 calc R . . H10B H 0.4621 0.1067 0.0966 0.035 Uiso 1 1 calc R . . C11 C 0.7762(3) 0.2436(2) 0.35614(10) 0.0359(5) Uani 1 1 d . . . H11A H 0.6575 0.2065 0.3564 0.054 Uiso 1 1 calc R . . H11B H 0.8083 0.3086 0.4005 0.054 Uiso 1 1 calc R . . H11C H 0.8553 0.1558 0.3574 0.054 Uiso 1 1 calc R . . C12 C 0.7290(3) 0.5497(2) 0.01749(12) 0.0406(5) Uani 1 1 d . . . H12A H 0.6425 0.5919 0.0473 0.061 Uiso 1 1 calc R . . H12B H 0.7100 0.5916 -0.0338 0.061 Uiso 1 1 calc R . . H12C H 0.8450 0.5779 0.0410 0.061 Uiso 1 1 calc R . . O1 O 1.17726(15) 0.25907(14) 0.27825(7) 0.0306(3) Uani 1 1 d . . . O2 O 1.09645(17) 0.14387(15) 0.02926(7) 0.0353(3) Uani 1 1 d . . . O4 O 1.16566(15) 0.22065(13) 0.15137(7) 0.0277(3) Uani 1 1 d . . . O5 O 0.78731(16) 0.33278(14) 0.28804(7) 0.0277(3) Uani 1 1 d . . . O6 O 0.71330(16) 0.38215(14) 0.01444(7) 0.0316(3) 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 C1 0.0254(9) 0.0177(8) 0.0293(11) 0.0008(8) 0.0016(8) 0.0058(7) C2 0.0254(9) 0.0178(8) 0.0247(10) 0.0013(7) 0.0032(7) -0.0001(7) C3 0.0232(9) 0.0243(8) 0.0218(10) -0.0037(7) 0.0023(7) 0.0008(7) C4 0.0229(9) 0.0186(8) 0.0296(10) -0.0014(8) 0.0011(7) 0.0024(7) C5 0.0232(9) 0.0239(9) 0.0249(10) 0.0029(8) -0.0008(7) 0.0018(8) C6 0.0267(10) 0.0240(9) 0.0226(10) -0.0037(8) 0.0031(7) -0.0013(7) C7 0.0244(9) 0.0179(8) 0.0258(10) 0.0000(7) 0.0049(7) -0.0004(7) C8 0.0291(10) 0.0199(9) 0.0303(11) -0.0006(8) 0.0046(8) 0.0030(8) C9 0.0244(10) 0.0323(10) 0.0317(11) 0.0005(8) 0.0066(8) -0.0019(8) C10 0.0242(10) 0.0290(9) 0.0346(11) -0.0040(9) 0.0016(8) -0.0024(8) C11 0.0420(12) 0.0413(11) 0.0255(11) -0.0010(9) 0.0086(9) -0.0032(9) C12 0.0520(13) 0.0291(10) 0.0386(12) 0.0104(9) -0.0034(10) -0.0038(10) O1 0.0291(7) 0.0290(7) 0.0324(8) -0.0048(6) -0.0017(6) 0.0018(6) O2 0.0406(8) 0.0348(7) 0.0329(8) -0.0039(6) 0.0143(6) -0.0069(6) O4 0.0242(7) 0.0288(7) 0.0306(8) -0.0020(6) 0.0050(5) -0.0028(5) O5 0.0337(7) 0.0289(7) 0.0212(7) -0.0031(5) 0.0056(5) 0.0005(6) O6 0.0414(8) 0.0274(7) 0.0250(7) 0.0038(6) -0.0005(6) 0.0012(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 C1 O1 1.1963(19) . ? C1 O4 1.387(2) . ? C1 C2 1.491(2) . ? C2 C7 1.531(2) . ? C2 C3 1.571(2) . ? C2 H2 0.9800 . ? C3 O5 1.4160(19) . ? C3 C4 1.505(2) . ? C3 C9 1.543(2) . ? C4 C5 1.331(2) . ? C4 H4 0.9300 . ? C5 O6 1.355(2) . ? C5 C6 1.505(2) . ? C6 C7 1.540(2) . ? C6 C10 1.541(2) . ? C6 H6 0.9800 . ? C7 C8 1.512(2) . ? C7 H7 0.9800 . ? C8 O2 1.190(2) . ? C8 O4 1.390(2) . ? C9 C10 1.548(2) . ? C9 H9A 0.9700 . ? C9 H9B 0.9700 . ? C10 H10A 0.9700 . ? C10 H10B 0.9700 . ? C11 O5 1.424(2) . ? C11 H11A 0.9600 . ? C11 H11B 0.9600 . ? C11 H11C 0.9600 . ? C12 O6 1.433(2) . ? 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 O1 C1 O4 119.65(16) . . ? O1 C1 C2 130.28(17) . . ? O4 C1 C2 110.07(14) . . ? C1 C2 C7 104.98(14) . . ? C1 C2 C3 112.81(13) . . ? C7 C2 C3 108.65(13) . . ? C1 C2 H2 110.1 . . ? C7 C2 H2 110.1 . . ? C3 C2 H2 110.1 . . ? O5 C3 C4 106.60(13) . . ? O5 C3 C9 114.48(14) . . ? C4 C3 C9 108.89(13) . . ? O5 C3 C2 112.99(13) . . ? C4 C3 C2 108.73(14) . . ? C9 C3 C2 105.01(13) . . ? C5 C4 C3 114.19(15) . . ? C5 C4 H4 122.9 . . ? C3 C4 H4 122.9 . . ? C4 C5 O6 129.84(16) . . ? C4 C5 C6 115.00(16) . . ? O6 C5 C6 115.16(15) . . ? C5 C6 C7 106.57(13) . . ? C5 C6 C10 108.19(14) . . ? C7 C6 C10 107.31(14) . . ? C5 C6 H6 111.5 . . ? C7 C6 H6 111.5 . . ? C10 C6 H6 111.5 . . ? C8 C7 C2 103.68(13) . . ? C8 C7 C6 111.27(14) . . ? C2 C7 C6 110.75(13) . . ? C8 C7 H7 110.3 . . ? C2 C7 H7 110.3 . . ? C6 C7 H7 110.3 . . ? O2 C8 O4 119.85(16) . . ? O2 C8 C7 130.16(17) . . ? O4 C8 C7 109.98(15) . . ? C3 C9 C10 109.26(14) . . ? C3 C9 H9A 109.8 . . ? C10 C9 H9A 109.8 . . ? C3 C9 H9B 109.8 . . ? C10 C9 H9B 109.8 . . ? H9A C9 H9B 108.3 . . ? C6 C10 C9 110.02(14) . . ? C6 C10 H10A 109.7 . . ? C9 C10 H10A 109.7 . . ? C6 C10 H10B 109.7 . . ? C9 C10 H10B 109.7 . . ? H10A C10 H10B 108.2 . . ? O5 C11 H11A 109.5 . . ? O5 C11 H11B 109.5 . . ? H11A C11 H11B 109.5 . . ? O5 C11 H11C 109.5 . . ? H11A C11 H11C 109.5 . . ? H11B C11 H11C 109.5 . . ? O6 C12 H12A 109.5 . . ? O6 C12 H12B 109.5 . . ? H12A C12 H12B 109.5 . . ? O6 C12 H12C 109.5 . . ? H12A C12 H12C 109.5 . . ? H12B C12 H12C 109.5 . . ? C1 O4 C8 110.56(13) . . ? C3 O5 C11 116.36(13) . . ? C5 O6 C12 115.25(14) . . ? 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 O1 C1 C2 C7 -171.64(17) . . . . ? O4 C1 C2 C7 8.37(17) . . . . ? O1 C1 C2 C3 70.2(2) . . . . ? O4 C1 C2 C3 -109.77(15) . . . . ? C1 C2 C3 O5 -52.42(19) . . . . ? C7 C2 C3 O5 -168.39(13) . . . . ? C1 C2 C3 C4 65.72(18) . . . . ? C7 C2 C3 C4 -50.25(17) . . . . ? C1 C2 C3 C9 -177.86(14) . . . . ? C7 C2 C3 C9 66.17(16) . . . . ? O5 C3 C4 C5 -179.77(14) . . . . ? C9 C3 C4 C5 -55.77(19) . . . . ? C2 C3 C4 C5 58.13(19) . . . . ? C3 C4 C5 O6 178.43(15) . . . . ? C3 C4 C5 C6 -2.4(2) . . . . ? C4 C5 C6 C7 -56.76(19) . . . . ? O6 C5 C6 C7 122.54(15) . . . . ? C4 C5 C6 C10 58.37(19) . . . . ? O6 C5 C6 C10 -122.34(16) . . . . ? C1 C2 C7 C8 -7.94(16) . . . . ? C3 C2 C7 C8 112.98(14) . . . . ? C1 C2 C7 C6 -127.37(14) . . . . ? C3 C2 C7 C6 -6.45(18) . . . . ? C5 C6 C7 C8 -55.76(18) . . . . ? C10 C6 C7 C8 -171.47(14) . . . . ? C5 C6 C7 C2 59.00(18) . . . . ? C10 C6 C7 C2 -56.71(17) . . . . ? C2 C7 C8 O2 -173.74(18) . . . . ? C6 C7 C8 O2 -54.7(2) . . . . ? C2 C7 C8 O4 5.30(17) . . . . ? C6 C7 C8 O4 124.37(14) . . . . ? O5 C3 C9 C10 174.29(14) . . . . ? C4 C3 C9 C10 55.11(18) . . . . ? C2 C3 C9 C10 -61.20(17) . . . . ? C5 C6 C10 C9 -53.11(18) . . . . ? C7 C6 C10 C9 61.52(17) . . . . ? C3 C9 C10 C6 -1.5(2) . . . . ? O1 C1 O4 C8 174.74(14) . . . . ? C2 C1 O4 C8 -5.27(17) . . . . ? O2 C8 O4 C1 178.93(15) . . . . ? C7 C8 O4 C1 -0.22(17) . . . . ? C4 C3 O5 C11 171.93(14) . . . . ? C9 C3 O5 C11 51.5(2) . . . . ? C2 C3 O5 C11 -68.70(18) . . . . ? C4 C5 O6 C12 2.8(3) . . . . ? C6 C5 O6 C12 -176.35(15) . . . . ? _diffrn_measured_fraction_theta_max 0.986 _diffrn_reflns_theta_full 27.52 _diffrn_measured_fraction_theta_full 0.986 _refine_diff_density_max 0.285 _refine_diff_density_min -0.184 _refine_diff_density_rms 0.046 # Attachment 'CMPD11.cif' data_jmwrg158 _database_code_depnum_ccdc_archive 'CCDC 647992' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C11 H17 N O3' _chemical_formula_weight 211.26 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 Orthorhombic _symmetry_space_group_name_H-M 'Cmc2(1) ' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, z+1/2' 'x, -y, z+1/2' '-x, y, z' 'x+1/2, y+1/2, z' '-x+1/2, -y+1/2, z+1/2' 'x+1/2, -y+1/2, z+1/2' '-x+1/2, y+1/2, z' _cell_length_a 9.3040(8) _cell_length_b 8.6876(7) _cell_length_c 12.6963(11) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 1026.23(15) _cell_formula_units_Z 4 _cell_measurement_temperature 130(2) _cell_measurement_reflns_used 2093 _cell_measurement_theta_min 3.21 _cell_measurement_theta_max 27.36 _exptl_crystal_description block _exptl_crystal_colour colourless _exptl_crystal_size_min 0.20 _exptl_crystal_size_mid 0.20 _exptl_crystal_size_max 0.30 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.367 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 456 _exptl_absorpt_coefficient_mu 0.099 _exptl_absorpt_correction_type none _exptl_absorpt_correction_T_min ? _exptl_absorpt_correction_T_max ? _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 130(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 '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 2583 _diffrn_reflns_av_R_equivalents 0.0289 _diffrn_reflns_av_sigmaI/netI 0.0217 _diffrn_reflns_limit_h_min -11 _diffrn_reflns_limit_h_max 10 _diffrn_reflns_limit_k_min -10 _diffrn_reflns_limit_k_max 8 _diffrn_reflns_limit_l_min -15 _diffrn_reflns_limit_l_max 14 _diffrn_reflns_theta_min 3.21 _diffrn_reflns_theta_max 24.98 _reflns_number_total 945 _reflns_number_gt 926 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'Bruker SMART' _computing_data_reduction 'Bruker SAINT' _computing_structure_solution 'Bruker SHELXTL' _computing_structure_refinement 'Bruker SHELXTL' _computing_molecular_graphics 'Bruker SHELXTL' _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^)+(0.0460P)^2^+0.2426P] 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 0.016(3) _refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^ _refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881' _refine_ls_abs_structure_Flack 0.0(15) _refine_ls_number_reflns 945 _refine_ls_number_parameters 85 _refine_ls_number_restraints 1 _refine_ls_R_factor_all 0.0288 _refine_ls_R_factor_gt 0.0284 _refine_ls_wR_factor_ref 0.0747 _refine_ls_wR_factor_gt 0.0744 _refine_ls_goodness_of_fit_ref 1.078 _refine_ls_restrained_S_all 1.078 _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 H51 H 0.085(2) 0.543(3) 0.2476(17) 0.048(6) Uiso 1 1 d . . . H50 H 0.0000 0.647(3) 0.323(3) 0.044(8) Uiso 1 2 d S . . N1 N 0.0000 0.7317(2) 0.17800(14) 0.0199(4) Uani 1 2 d S . . C9 C 0.08294(16) 0.71568(17) -0.08952(13) 0.0210(4) Uani 1 1 d . . . H9A H 0.1187 0.6360 -0.0403 0.025 Uiso 1 1 calc R . . H9B H 0.1187 0.6908 -0.1609 0.025 Uiso 1 1 calc R . . O1 O 0.24380(12) 0.75187(13) 0.15936(9) 0.0261(3) Uani 1 1 d . . . C2 C 0.08296(16) 0.91406(16) 0.05490(11) 0.0179(4) Uani 1 1 d . . . H2 H 0.1199 1.0171 0.0773 0.021 Uiso 1 1 calc R . . C11 C 0.0000 0.6082(3) 0.25537(19) 0.0270(5) Uani 1 2 d S . . C1 C 0.12379(15) 0.79316(16) 0.13515(12) 0.0192(3) Uani 1 1 d . . . C4 C 0.08346(15) 0.99641(19) -0.13244(13) 0.0231(4) Uani 1 1 d . . . H4A H 0.1193 0.9745 -0.2043 0.028 Uiso 1 1 calc R . . H4B H 0.1193 1.0991 -0.1111 0.028 Uiso 1 1 calc R . . C3 C 0.13944(15) 0.87401(16) -0.05584(11) 0.0189(4) Uani 1 1 d . . . H3 H 0.2469 0.8738 -0.0558 0.023 Uiso 1 1 calc R . . O4 O 0.5000 0.8452(3) 0.04531(16) 0.0399(5) Uani 1 2 d S . . H59 H 0.578(3) 0.813(3) 0.085(2) 0.067(8) Uiso 1 1 d . . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 N1 0.0221(10) 0.0211(9) 0.0164(8) 0.0004(7) 0.000 0.000 C9 0.0204(8) 0.0238(8) 0.0187(7) -0.0020(6) 0.0010(7) 0.0034(6) O1 0.0194(5) 0.0354(6) 0.0234(6) 0.0028(4) -0.0040(4) 0.0043(4) C2 0.0168(8) 0.0176(6) 0.0192(7) -0.0010(6) -0.0008(6) -0.0011(6) C11 0.0336(14) 0.0251(11) 0.0223(11) 0.0063(10) 0.000 0.000 C1 0.0209(8) 0.0208(7) 0.0161(6) -0.0049(6) -0.0030(7) -0.0001(6) C4 0.0204(8) 0.0253(8) 0.0236(7) 0.0061(6) 0.0019(6) -0.0010(7) C3 0.0146(7) 0.0228(8) 0.0193(7) 0.0002(6) 0.0013(6) -0.0002(6) O4 0.0268(11) 0.0552(12) 0.0376(10) 0.0106(9) 0.000 0.000 _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag N1 C1 1.3810(18) . ? N1 C1 1.3810(18) 4 ? N1 C11 1.455(3) . ? C9 C3 1.533(2) . ? C9 C9 1.543(3) 4 ? C9 H9A 0.9900 . ? C9 H9B 0.9900 . ? O1 C1 1.2124(19) . ? C2 C1 1.512(2) . ? C2 C3 1.541(2) . ? C2 C2 1.544(3) 4 ? C2 H2 1.0000 . ? C11 H51 0.98(2) . ? C11 H50 0.93(3) . ? C4 C3 1.532(2) . ? C4 C4 1.553(3) 4 ? C4 H4A 0.9900 . ? C4 H4B 0.9900 . ? C3 H3 1.0000 . ? O4 H59 0.92(3) . ? 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 N1 C1 113.02(17) . 4 ? C1 N1 C11 123.44(9) . . ? C1 N1 C11 123.44(9) 4 . ? C3 C9 C9 110.05(7) . 4 ? C3 C9 H9A 109.7 . . ? C9 C9 H9A 109.7 4 . ? C3 C9 H9B 109.7 . . ? C9 C9 H9B 109.7 4 . ? H9A C9 H9B 108.2 . . ? C1 C2 C3 111.86(11) . . ? C1 C2 C2 104.55(8) . 4 ? C3 C2 C2 109.94(8) . 4 ? C1 C2 H2 110.1 . . ? C3 C2 H2 110.1 . . ? C2 C2 H2 110.1 4 . ? N1 C11 H51 111.0(13) . . ? N1 C11 H50 111.0(19) . . ? H51 C11 H50 107.8(16) . . ? O1 C1 N1 123.63(15) . . ? O1 C1 C2 127.43(15) . . ? N1 C1 C2 108.93(12) . . ? C3 C4 C4 109.87(8) . 4 ? C3 C4 H4A 109.7 . . ? C4 C4 H4A 109.7 4 . ? C3 C4 H4B 109.7 . . ? C4 C4 H4B 109.7 4 . ? H4A C4 H4B 108.2 . . ? C4 C3 C9 109.21(13) . . ? C4 C3 C2 107.85(11) . . ? C9 C3 C2 109.89(12) . . ? C4 C3 H3 110.0 . . ? C9 C3 H3 110.0 . . ? C2 C3 H3 110.0 . . ? 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 C1 N1 C1 O1 -177.68(10) 4 . . . ? C11 N1 C1 O1 -1.4(3) . . . . ? C1 N1 C1 C2 1.4(2) 4 . . . ? C11 N1 C1 C2 177.75(18) . . . . ? C3 C2 C1 O1 59.3(2) . . . . ? C2 C2 C1 O1 178.26(13) 4 . . . ? C3 C2 C1 N1 -119.76(14) . . . . ? C2 C2 C1 N1 -0.82(12) 4 . . . ? C4 C4 C3 C9 59.21(12) 4 . . . ? C4 C4 C3 C2 -60.17(11) 4 . . . ? C9 C9 C3 C4 -59.31(12) 4 . . . ? C9 C9 C3 C2 58.80(11) 4 . . . ? C1 C2 C3 C4 175.91(12) . . . . ? C2 C2 C3 C4 60.22(11) 4 . . . ? C1 C2 C3 C9 56.97(16) . . . . ? C2 C2 C3 C9 -58.73(11) 4 . . . ? _diffrn_measured_fraction_theta_max 1.000 _diffrn_reflns_theta_full 24.98 _diffrn_measured_fraction_theta_full 1.000 _refine_diff_density_max 0.164 _refine_diff_density_min -0.182 _refine_diff_density_rms 0.037