#------------------------------------------------------------------------------ #$Date: 2021-12-07 05:54:57 +0200 (Tue, 07 Dec 2021) $ #$Revision: 271226 $ #$URL: file:///home/coder/svn-repositories/cod/cif/7/15/83/7158387.cif $ #------------------------------------------------------------------------------ # # This file is available in the Crystallography Open Database (COD), # http://www.crystallography.net/ # # All data on this site have been placed in the public domain by the # contributors. # data_7158387 loop_ _publ_author_name 'Goryaeva, Marina V.' 'Kushch, Svetlana O.' 'Burgart, Yanina V.' 'Ezhikova, Marina A.' 'Kodess, Mikhail I.' 'Slepukhin, Pavel A.' 'Triandafilova, Galina A.' 'Krasnykh, Olga P.' 'Yakovleva, Ekaterina I.' 'Zarubaev, Vladimir V.' 'Sinegubova, Ekaterina O.' 'Esaulkova, Iana L.' 'Shtro, Anna A.' 'Galochkina, Anastasia V.' 'Nikolaeva, Yulia V.' 'Saloutin, Victor I.' _publ_section_title ; New heteroanalogs of tricyclic ascidian alkaloids: synthesis and biological activity. ; _journal_issue 45 _journal_name_full 'Organic & biomolecular chemistry' _journal_page_first 9925 _journal_page_last 9935 _journal_paper_doi 10.1039/d1ob01843d _journal_volume 19 _journal_year 2021 _chemical_formula_moiety 'C12 H16 F3 N O3' _chemical_formula_sum 'C12 H16 F3 N O3' _chemical_formula_weight 279.26 _space_group_crystal_system triclinic _space_group_IT_number 2 _space_group_name_Hall '-P 1' _space_group_name_H-M_alt 'P -1' _atom_sites_solution_hydrogens geom _atom_sites_solution_primary iterative _atom_sites_solution_secondary difmap _audit_creation_date 2021-03-09 _audit_creation_method ; Olex2 1.2-ac2 (compiled 2012.03.27 svn.r2268, GUI svn.r4156) ; _audit_update_record ; 2021-09-04 deposited with the CCDC. 2021-10-28 downloaded from the CCDC. ; _cell_angle_alpha 77.963(4) _cell_angle_beta 77.679(4) _cell_angle_gamma 76.073(4) _cell_formula_units_Z 2 _cell_length_a 5.6852(3) _cell_length_b 9.4367(4) _cell_length_c 12.6134(6) _cell_measurement_reflns_used 1919 _cell_measurement_temperature 295(2) _cell_measurement_theta_max 27.0210 _cell_measurement_theta_min 3.0360 _cell_volume 632.80(5) _computing_cell_refinement 'CrysAlisPro 1.171.41.98a (Rigaku OD, 2021)' _computing_data_collection 'CrysAlisPro 1.171.41.98a (Rigaku OD, 2021)' _computing_data_reduction 'CrysAlisPro 1.171.41.98a (Rigaku OD, 2021)' _computing_molecular_graphics ; O. V. Dolomanov, L. J. Bourhis, R. J. Gildea, J. A. K. Howard and H. Puschmann, OLEX2: a complete structure solution, refinement and analysis program. J. Appl. Cryst. (2009). 42, 339-341. ; _computing_publication_material ; O. V. Dolomanov, L. J. Bourhis, R. J. Gildea, J. A. K. Howard and H. Puschmann, OLEX2: a complete structure solution, refinement and analysis program. J. Appl. Cryst. (2009). 42, 339-341. ; _computing_structure_refinement ; SHELXL, G.M. Sheldrick, Acta Cryst. (2008). A64, 112-122 ; _computing_structure_solution 'J. Appl. Cryst. (2007) 40, 786-790' _diffrn_ambient_temperature 295(2) _diffrn_detector 'CCD plate' _diffrn_detector_area_resol_mean 15.9555 _diffrn_detector_type Eos _diffrn_measured_fraction_theta_full 0.9996 _diffrn_measured_fraction_theta_max 0.8641 _diffrn_measurement_details ; List of Runs (angles in degrees, time in seconds): # Type Start End Width t~exp~ \w \q \k \f Frames #-------------------------------------------------------------------------- 1 \w -49.00 34.00 1.00 7.50 -- 17.59 -57.00 -60.00 83 2 \w -41.00 34.00 1.00 7.50 -- 17.59 -57.00-180.00 75 3 \w -9.00 32.00 1.00 7.50 -- 17.59 77.00 60.00 41 4 \w -9.00 36.00 1.00 7.50 -- 17.59 77.00 -60.00 45 5 \w 5.00 38.00 1.00 7.50 -- 17.59 77.00 150.00 33 6 \w -16.00 10.00 1.00 7.50 -- 17.59 -99.00 -90.00 26 7 \w 14.00 85.00 1.00 7.50 -- 17.59 57.00 90.00 71 ; _diffrn_measurement_device 'four-circle diffractometer' _diffrn_measurement_device_type 'Xcalibur, Eos' _diffrn_measurement_method '\w scans' _diffrn_orient_matrix_type 'CrysAlisPro convention (1999,Acta A55,543-557)' _diffrn_orient_matrix_UB_11 -0.0539702000 _diffrn_orient_matrix_UB_12 -0.0538551000 _diffrn_orient_matrix_UB_13 0.0392856000 _diffrn_orient_matrix_UB_21 0.1057235000 _diffrn_orient_matrix_UB_22 -0.0199426000 _diffrn_orient_matrix_UB_23 0.0255149000 _diffrn_orient_matrix_UB_31 -0.0541849000 _diffrn_orient_matrix_UB_32 0.0535577000 _diffrn_orient_matrix_UB_33 0.0348190000 _diffrn_radiation_monochromator graphite _diffrn_radiation_probe x-ray _diffrn_radiation_type 'Mo K\a' _diffrn_radiation_wavelength 0.71073 _diffrn_reflns_av_R_equivalents 0.0212 _diffrn_reflns_av_unetI/netI 0.0447 _diffrn_reflns_limit_h_max 6 _diffrn_reflns_limit_h_min -7 _diffrn_reflns_limit_k_max 12 _diffrn_reflns_limit_k_min -12 _diffrn_reflns_limit_l_max 11 _diffrn_reflns_limit_l_min -15 _diffrn_reflns_number 5210 _diffrn_reflns_theta_full 26.00 _diffrn_reflns_theta_max 29.10 _diffrn_reflns_theta_min 1.68 _diffrn_source 'fine-focus sealed X-ray tube' _diffrn_source_type 'Enhance (Mo) X-ray Source' _exptl_absorpt_coefficient_mu 0.133 _exptl_absorpt_correction_T_max 1.00000 _exptl_absorpt_correction_T_min 0.86156 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details ; CrysAlisPro 1.171.41.98a (Rigaku Oxford Diffraction, 2021) Empirical absorption correction using spherical harmonics, implemented in SCALE3 ABSPACK scaling algorithm. ; _exptl_crystal_colour colourless _exptl_crystal_colour_primary colourless _exptl_crystal_density_diffrn 1.466 _exptl_crystal_density_method 'not measured' _exptl_crystal_description block _exptl_crystal_F_000 292 _exptl_crystal_size_max 0.44 _exptl_crystal_size_mid 0.31 _exptl_crystal_size_min 0.22 _refine_diff_density_max 0.167 _refine_diff_density_min -0.194 _refine_diff_density_rms 0.046 _refine_ls_extinction_method none _refine_ls_goodness_of_fit_ref 1.001 _refine_ls_hydrogen_treatment mixed _refine_ls_matrix_type full _refine_ls_number_parameters 236 _refine_ls_number_reflns 2929 _refine_ls_number_restraints 0 _refine_ls_restrained_S_all 1.001 _refine_ls_R_factor_all 0.0884 _refine_ls_R_factor_gt 0.0501 _refine_ls_shift/su_max 0.000 _refine_ls_shift/su_mean 0.000 _refine_ls_structure_factor_coef Fsqd _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0650P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_gt 0.1116 _refine_ls_wR_factor_ref 0.1374 _reflns_number_gt 1854 _reflns_number_total 2929 _reflns_threshold_expression >2sigma(I) _cod_data_source_file d1ob01843d2.cif _cod_data_source_block exp_1145 _cod_depositor_comments 'Adding full bibliography for 7158386--7158394.cif.' _cod_database_code 7158387 _reflns_odcompleteness_completeness 99.96 _reflns_odcompleteness_iscentric 1 _reflns_odcompleteness_theta 26.32 _oxdiff_exptl_absorpt_empirical_details ; Empirical correction (ABSPACK) includes: - Absorption correction using spherical harmonics - Frame scaling ; _oxdiff_exptl_absorpt_empirical_full_max 1.077 _oxdiff_exptl_absorpt_empirical_full_min 0.900 loop_ _space_group_symop_id _space_group_symop_operation_xyz 1 'x, y, z' 2 '-x, -y, -z' 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 0.1943(2) 0.08533(12) 0.82293(10) 0.0416(3) Uani 1 1 d . . . F2 F -0.0874(3) 0.72733(12) 0.71355(12) 0.0797(5) Uani 1 1 d . . . F3 F -0.2686(3) 0.62979(14) 0.86793(13) 0.0864(5) Uani 1 1 d . . . O2 O -0.2901(2) 0.49064(15) 0.69690(12) 0.0488(4) Uani 1 1 d . . . F1 F 0.1249(3) 0.58910(14) 0.83242(13) 0.0841(5) Uani 1 1 d . . . O3 O 0.2961(3) 0.31853(15) 0.49597(12) 0.0654(5) Uani 1 1 d . . . N1 N 0.0919(3) 0.20452(16) 0.65153(12) 0.0436(4) Uani 1 1 d . . . C2 C 0.0047(3) 0.18547(17) 0.76990(14) 0.0367(4) Uani 1 1 d . . . C9 C 0.1876(4) 0.3196(2) 0.59197(16) 0.0452(5) Uani 1 1 d . . . C7 C -0.0679(3) 0.46802(18) 0.73694(15) 0.0397(4) Uani 1 1 d . . . C6 C -0.0465(4) 0.32668(18) 0.82304(15) 0.0381(4) Uani 1 1 d . . . C1 C -0.0758(4) 0.6032(2) 0.7884(2) 0.0566(6) Uani 1 1 d . . . C8 C 0.1561(4) 0.4527(2) 0.64555(18) 0.0453(5) Uani 1 1 d . . . C4 C -0.3272(5) 0.1624(2) 0.91998(19) 0.0557(6) Uani 1 1 d . . . C10 C 0.3468(5) -0.0423(3) 0.6648(2) 0.0625(7) Uani 1 1 d . . . C11 C 0.1513(5) 0.0638(2) 0.6071(2) 0.0573(6) Uani 1 1 d . . . C12 C 0.2690(5) -0.0578(2) 0.78795(19) 0.0548(6) Uani 1 1 d . . . C3 C -0.2380(4) 0.1317(3) 0.80367(18) 0.0494(5) Uani 1 1 d . . . C5 C -0.2766(5) 0.3155(2) 0.91270(19) 0.0555(6) Uani 1 1 d . . . H6 H 0.091(3) 0.3203(17) 0.8587(14) 0.035(5) Uiso 1 1 d . . . H3A H -0.346(4) 0.191(2) 0.7543(17) 0.061(6) Uiso 1 1 d . . . H12A H 0.119(4) -0.110(2) 0.8172(16) 0.053(6) Uiso 1 1 d . . . H4A H -0.227(4) 0.093(2) 0.9742(18) 0.068(7) Uiso 1 1 d . . . H11A H 0.192(4) 0.091(2) 0.5294(18) 0.056(6) Uiso 1 1 d . . . H5A H -0.260(4) 0.334(2) 0.983(2) 0.065(7) Uiso 1 1 d . . . H10A H 0.498(5) 0.000(2) 0.6432(19) 0.070(7) Uiso 1 1 d . . . H11B H -0.013(5) 0.030(2) 0.6248(19) 0.073(7) Uiso 1 1 d . . . H10B H 0.373(4) -0.137(3) 0.6428(17) 0.072(7) Uiso 1 1 d . . . H8A H 0.299(4) 0.443(2) 0.6766(16) 0.054(6) Uiso 1 1 d . . . H12B H 0.411(4) -0.110(2) 0.8311(17) 0.063(6) Uiso 1 1 d . . . H2 H -0.291(5) 0.553(3) 0.637(2) 0.074(8) Uiso 1 1 d . . . H3B H -0.222(4) 0.023(2) 0.7961(17) 0.071(7) Uiso 1 1 d . . . H4B H -0.500(5) 0.161(2) 0.9461(19) 0.070(7) Uiso 1 1 d . . . H5B H -0.414(5) 0.386(3) 0.887(2) 0.084(8) Uiso 1 1 d . . . H8B H 0.147(4) 0.537(2) 0.5869(17) 0.057(6) 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 0.0395(8) 0.0348(6) 0.0486(8) -0.0068(5) -0.0113(6) -0.0007(5) F2 0.0926(12) 0.0342(7) 0.1108(12) -0.0053(6) -0.0238(9) -0.0103(6) F3 0.0873(12) 0.0621(8) 0.1010(12) -0.0410(8) 0.0117(9) 0.0002(7) O2 0.0360(8) 0.0510(8) 0.0534(9) 0.0052(7) -0.0109(7) -0.0067(6) F1 0.0859(11) 0.0591(8) 0.1262(13) -0.0387(8) -0.0497(10) -0.0027(7) O3 0.0720(12) 0.0593(9) 0.0448(9) 0.0027(7) 0.0074(8) -0.0001(8) N1 0.0527(10) 0.0423(9) 0.0356(9) -0.0076(6) -0.0049(8) -0.0112(7) C2 0.0378(11) 0.0336(9) 0.0375(10) -0.0037(7) -0.0085(8) -0.0056(7) C9 0.0396(12) 0.0455(11) 0.0429(11) -0.0008(8) -0.0052(9) -0.0015(8) C7 0.0325(10) 0.0351(9) 0.0500(11) -0.0051(8) -0.0095(9) -0.0035(7) C6 0.0381(11) 0.0374(9) 0.0398(11) -0.0085(7) -0.0100(9) -0.0049(8) C1 0.0538(14) 0.0401(11) 0.0746(16) -0.0118(10) -0.0131(12) -0.0033(9) C8 0.0347(11) 0.0394(11) 0.0568(13) 0.0010(9) -0.0052(10) -0.0081(8) C4 0.0434(14) 0.0612(14) 0.0559(14) -0.0003(10) -0.0005(11) -0.0134(11) C10 0.0638(17) 0.0476(13) 0.0750(17) -0.0274(11) -0.0014(13) -0.0035(11) C11 0.0752(18) 0.0543(13) 0.0461(14) -0.0198(10) -0.0057(13) -0.0143(12) C12 0.0588(15) 0.0364(11) 0.0659(15) -0.0120(9) -0.0116(12) 0.0005(10) C3 0.0410(12) 0.0543(13) 0.0556(13) -0.0062(10) -0.0102(10) -0.0159(9) C5 0.0590(15) 0.0556(13) 0.0425(12) -0.0071(10) 0.0019(11) -0.0042(11) 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' F F 0.0171 0.0103 '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' 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 C2 O1 C12 114.19(14) . . ? C7 O2 H2 111.6(17) . . ? C2 N1 C11 113.07(15) . . ? C9 N1 C2 124.87(14) . . ? C9 N1 C11 118.76(17) . . ? O1 C2 N1 108.22(14) . . ? O1 C2 C6 104.19(13) . . ? O1 C2 C3 111.24(15) . . ? N1 C2 C6 115.81(14) . . ? N1 C2 C3 113.07(15) . . ? C3 C2 C6 103.96(16) . . ? O3 C9 N1 121.99(17) . . ? O3 C9 C8 120.30(18) . . ? N1 C9 C8 117.71(17) . . ? O2 C7 C6 108.67(15) . . ? O2 C7 C1 107.86(14) . . ? O2 C7 C8 112.11(16) . . ? C6 C7 C1 110.78(16) . . ? C8 C7 C6 109.10(14) . . ? C8 C7 C1 108.33(16) . . ? C2 C6 H6 107.4(10) . . ? C7 C6 C2 111.88(14) . . ? C7 C6 C5 115.37(15) . . ? C7 C6 H6 108.4(10) . . ? C5 C6 C2 105.17(15) . . ? C5 C6 H6 108.3(11) . . ? F2 C1 C7 111.62(18) . . ? F3 C1 F2 105.98(16) . . ? F3 C1 F1 106.55(19) . . ? F3 C1 C7 113.68(18) . . ? F1 C1 F2 106.39(18) . . ? F1 C1 C7 112.11(16) . . ? C9 C8 C7 112.88(16) . . ? C9 C8 H8A 108.3(12) . . ? C9 C8 H8B 105.8(12) . . ? C7 C8 H8A 108.4(13) . . ? C7 C8 H8B 112.4(13) . . ? H8A C8 H8B 109.0(18) . . ? C3 C4 C5 103.06(18) . . ? C3 C4 H4A 112.7(12) . . ? C3 C4 H4B 113.5(14) . . ? C5 C4 H4A 106.9(12) . . ? C5 C4 H4B 111.4(13) . . ? H4A C4 H4B 109.1(18) . . ? C11 C10 H10A 107.2(13) . . ? C11 C10 H10B 108.7(14) . . ? C12 C10 C11 110.8(2) . . ? C12 C10 H10A 108.9(14) . . ? C12 C10 H10B 109.5(13) . . ? H10A C10 H10B 111.7(19) . . ? N1 C11 C10 108.05(18) . . ? N1 C11 H11A 105.2(12) . . ? N1 C11 H11B 103.6(13) . . ? C10 C11 H11A 117.3(13) . . ? C10 C11 H11B 113.1(13) . . ? H11A C11 H11B 108.5(19) . . ? O1 C12 C10 111.20(17) . . ? O1 C12 H12A 106.1(11) . . ? O1 C12 H12B 102.2(11) . . ? C10 C12 H12A 113.0(11) . . ? C10 C12 H12B 113.5(12) . . ? H12A C12 H12B 110.0(17) . . ? C2 C3 H3A 106.9(13) . . ? C2 C3 H3B 113.8(13) . . ? C4 C3 C2 103.38(17) . . ? C4 C3 H3A 112.0(12) . . ? C4 C3 H3B 114.0(12) . . ? H3A C3 H3B 106.7(17) . . ? C6 C5 H5A 113.6(14) . . ? C6 C5 H5B 107.8(15) . . ? C4 C5 C6 106.25(17) . . ? C4 C5 H5A 112.4(13) . . ? C4 C5 H5B 106.9(15) . . ? H5A C5 H5B 109.5(19) . . ? 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 C2 1.434(2) . ? O1 C12 1.446(2) . ? F2 C1 1.341(2) . ? F3 C1 1.332(3) . ? O2 C7 1.412(2) . ? O2 H2 0.85(2) . ? F1 C1 1.339(3) . ? O3 C9 1.237(2) . ? N1 C2 1.457(2) . ? N1 C9 1.345(2) . ? N1 C11 1.485(2) . ? C2 C6 1.553(2) . ? C2 C3 1.529(3) . ? C9 C8 1.504(3) . ? C7 C6 1.532(2) . ? C7 C1 1.535(3) . ? C7 C8 1.525(3) . ? C6 C5 1.545(3) . ? C6 H6 0.964(18) . ? C8 H8A 0.96(2) . ? C8 H8B 0.96(2) . ? C4 C3 1.511(3) . ? C4 C5 1.520(3) . ? C4 H4A 1.01(2) . ? C4 H4B 0.97(3) . ? C10 C11 1.508(3) . ? C10 C12 1.507(3) . ? C10 H10A 1.00(3) . ? C10 H10B 0.96(2) . ? C11 H11A 0.95(2) . ? C11 H11B 1.02(3) . ? C12 H12A 1.04(2) . ? C12 H12B 1.04(2) . ? C3 H3A 0.96(2) . ? C3 H3B 1.03(2) . ? C5 H5A 0.96(2) . ? C5 H5B 0.97(3) . ? 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 C2 C6 C7 135.54(15) . . . . ? O1 C2 C6 C5 -98.49(17) . . . . ? O1 C2 C3 C4 73.8(2) . . . . ? O2 C7 C6 C2 70.98(19) . . . . ? O2 C7 C6 C5 -49.2(2) . . . . ? O2 C7 C1 F2 -63.0(2) . . . . ? O2 C7 C1 F3 56.8(2) . . . . ? O2 C7 C1 F1 177.75(18) . . . . ? O2 C7 C8 C9 -63.3(2) . . . . ? O3 C9 C8 C7 153.79(19) . . . . ? N1 C2 C6 C7 16.8(2) . . . . ? N1 C2 C6 C5 142.78(17) . . . . ? N1 C2 C3 C4 -164.22(15) . . . . ? N1 C9 C8 C7 -25.5(2) . . . . ? C2 O1 C12 C10 55.1(2) . . . . ? C2 N1 C9 O3 167.58(18) . . . . ? C2 N1 C9 C8 -13.1(3) . . . . ? C2 N1 C11 C10 -58.9(3) . . . . ? C2 C6 C5 C4 8.0(2) . . . . ? C9 N1 C2 O1 -99.00(19) . . . . ? C9 N1 C2 C6 17.5(3) . . . . ? C9 N1 C2 C3 137.3(2) . . . . ? C9 N1 C11 C10 101.6(2) . . . . ? C7 C6 C5 C4 131.73(19) . . . . ? C6 C2 C3 C4 -37.8(2) . . . . ? C6 C7 C1 F2 178.19(17) . . . . ? C6 C7 C1 F3 -62.0(2) . . . . ? C6 C7 C1 F1 58.9(2) . . . . ? C6 C7 C8 C9 57.1(2) . . . . ? C1 C7 C6 C2 -170.69(16) . . . . ? C1 C7 C6 C5 69.1(2) . . . . ? C1 C7 C8 C9 177.78(16) . . . . ? C8 C7 C6 C2 -51.5(2) . . . . ? C8 C7 C6 C5 -171.70(17) . . . . ? C8 C7 C1 F2 58.6(2) . . . . ? C8 C7 C1 F3 178.38(17) . . . . ? C8 C7 C1 F1 -60.7(2) . . . . ? C11 N1 C2 O1 60.1(2) . . . . ? C11 N1 C2 C6 176.58(17) . . . . ? C11 N1 C2 C3 -63.6(2) . . . . ? C11 N1 C9 O3 9.6(3) . . . . ? C11 N1 C9 C8 -171.14(18) . . . . ? C11 C10 C12 O1 -52.1(3) . . . . ? C12 O1 C2 N1 -57.69(19) . . . . ? C12 O1 C2 C6 178.53(16) . . . . ? C12 O1 C2 C3 67.1(2) . . . . ? C12 C10 C11 N1 53.2(3) . . . . ? C3 C2 C6 C7 -107.84(18) . . . . ? C3 C2 C6 C5 18.12(19) . . . . ? C3 C4 C5 C6 -31.3(2) . . . . ? C5 C4 C3 C2 42.9(2) . . . . ?