# Supplementary Material (ESI) for Organic & Biomolecular Chemistry # This journal is (c) The Royal Society of Chemistry 2011 data_global _journal_name_full Org.Biomol.Chem. _journal_coden_Cambridge 0177 _publ_contact_author_name 'Hans-Joachim Knolker' _publ_contact_author_address ; ; _publ_contact_author_email hans-joachim.knoelker@tu-dresden.de loop_ _publ_author_name 'K. K. Gruner' 'T. Hopfmann' 'K. Matsumoto' 'A. Jager' 'T. Katsuki' ; H.-J.Knolker ; # Attachment 'an147.cif' data_an147 _database_code_depnum_ccdc_archive 'CCDC 801747' #TrackingRef 'an147.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ? _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C18 H17 N O' _chemical_formula_sum 'C18 H17 N O' _chemical_formula_weight 263.33 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 monoclinic _symmetry_space_group_name_H-M 'C c' _symmetry_space_group_name_Hall 'C -2yc' _symmetry_int_tables_number 9 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' 'x, -y, z+1/2' 'x+1/2, y+1/2, z' 'x+1/2, -y+1/2, z+1/2' _cell_length_a 11.960(2) _cell_length_b 16.344(3) _cell_length_c 7.655(2) _cell_angle_alpha 90.00 _cell_angle_beta 109.03(3) _cell_angle_gamma 90.00 _cell_volume 1414.6(5) _cell_formula_units_Z 4 _cell_measurement_temperature 198(2) _cell_measurement_reflns_used 533 _cell_measurement_theta_min 4.026 _cell_measurement_theta_max 24.754 _exptl_crystal_description bock _exptl_crystal_colour colourless _exptl_crystal_size_max 0.42 _exptl_crystal_size_mid 0.17 _exptl_crystal_size_min 0.09 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.236 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 560 _exptl_absorpt_coefficient_mu 0.076 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.9119 _exptl_absorpt_correction_T_max 0.9932 _exptl_absorpt_process_details 'SADABS version 2.10 (Sheldrick,Bruker AXS Inc.,2002)' _publ_section_references ; !!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!! !!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!! !!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!! These references have to be cited in the publication, because they named software was used for measurement, evaluation of data, solution, refinement and computing the publication material of the structure. They are in ACTACC-format and need to be changed for publication in another journal. !!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!! !!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!! !!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!! Allen, F. H., Johnson, O., Shields, G. P., Smith, B. R. & Towler, M. (2004). J. Appl. Cryst. 37, 331-334. Burla, M. C., Caliandro, R.,Camalli, M., Carrozzini, B., Cascarano, G. L., De Caro, L., Giacovazzo, C., Polidori, G. & Spagna, R. (2005). J. Appl. Cryst. 38, 381-388. Duisenberg, A. J. M. (1992). J. Appl. Cryst. 25, 92-96. Duisenberg, A. J. M., Kroon-Batenburg, L. M. J. & Schreurs, A. M. M. (2003). J. Appl. Cryst. 36, 220-229. Farrugia, L. J. (1997). J. Appl. Cryst. 30, 565. Farrugia, L. J. (1999). WinGX. J. Appl. Cryst. 32, 837-838. Hall, S. R., Allen, F. H. & Brown, I. D. (1991). Acta Cryst. A47, 655-685. Nonius (1999). COLLECT. Nonius BV, Delft, The Netherlands. Sheldrick, G. M. (1997). SHELX97. Programs for Crystal Structure Analysis (Release 97-2). University of G\"ottingen, Germany. Sheldrick, G. M. (2002). SADABS, Version 2.10, Bruker Analytical X-Ray Systems, Inc.: Madison, WI. Spek, A. L. (2005). PLATON, A Multipurpose Crystallographic Tool. Utrecht University, Utrecht, The Netherlands. ; _exptl_special_details ; ? ; _diffrn_ambient_temperature 198(2) _diffrn_radiation_probe x-ray _diffrn_radiation_type MoK\a _diffrn_radiation_wavelength 0.71073 _diffrn_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type KappaCCD _diffrn_measurement_method \f _diffrn_detector_area_resol_mean 9 _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 24148 _diffrn_reflns_av_R_equivalents 0.0753 _diffrn_reflns_av_sigmaI/netI 0.0394 _diffrn_reflns_limit_h_min -15 _diffrn_reflns_limit_h_max 15 _diffrn_reflns_limit_k_min -21 _diffrn_reflns_limit_k_max 21 _diffrn_reflns_limit_l_min -10 _diffrn_reflns_limit_l_max 10 _diffrn_reflns_theta_min 3.07 _diffrn_reflns_theta_max 28.00 _reflns_number_total 3367 _reflns_number_gt 2602 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Collect (Nonius BV, 1999)' _computing_cell_refinement 'Dirax/lsq (Duisenberg, 1992)' _computing_data_reduction 'EvalCCD (Duisenberg et al., 2003)' _computing_structure_solution 'SIR2004 (Burla et al., 2005)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997), WinGX (Farrugia 1999), PLATON (Spek 2005)' _computing_molecular_graphics 'ORTEP-3 for Windows (Farrugia, 1997)' _computing_publication_material 'WinGX (Farrugia 1999), enCIFer (Allen et al. 2004)' _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^+0.0152P] 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_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881' _refine_ls_abs_structure_Flack 0.1(11) _refine_ls_number_reflns 3367 _refine_ls_number_parameters 188 _refine_ls_number_restraints 2 _refine_ls_R_factor_all 0.0593 _refine_ls_R_factor_gt 0.0375 _refine_ls_wR_factor_ref 0.0811 _refine_ls_wR_factor_gt 0.0747 _refine_ls_goodness_of_fit_ref 1.037 _refine_ls_restrained_S_all 1.036 _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 C1 C 0.73965(14) 0.70423(8) 0.81443(18) 0.0292(3) Uani 1 1 d . . . C2 C 0.63649(13) 0.66215(9) 0.72083(17) 0.0303(3) Uani 1 1 d . . . O2 O 0.52900(8) 0.69375(6) 0.71935(11) 0.0330(3) Uani 1 1 d . . . C3 C 0.63358(14) 0.59137(9) 0.61446(18) 0.0339(4) Uani 1 1 d . . . C4 C 0.74051(14) 0.55899(9) 0.61314(18) 0.0352(4) Uani 1 1 d . . . H4 H 0.7409 0.5111 0.5431 0.042 Uiso 1 1 calc R . . C4A C 0.84740(14) 0.59579(9) 0.71329(17) 0.0322(3) Uani 1 1 d . . . C4B C 0.97025(15) 0.57757(9) 0.74291(19) 0.0332(3) Uani 1 1 d . . . C5 C 1.02974(15) 0.51409(10) 0.6896(2) 0.0397(4) Uani 1 1 d . . . H5 H 0.9867 0.4708 0.6145 0.048 Uiso 1 1 calc R . . C6 C 1.15134(17) 0.51451(11) 0.7465(2) 0.0443(4) Uani 1 1 d . . . H6 H 1.1921 0.4710 0.7112 0.053 Uiso 1 1 calc R . . C7 C 1.21559(15) 0.57818(10) 0.8559(2) 0.0430(4) Uani 1 1 d . . . H7 H 1.2995 0.5775 0.8921 0.052 Uiso 1 1 calc R . . C8 C 1.15963(14) 0.64217(10) 0.9124(2) 0.0375(4) Uani 1 1 d . . . H8 H 1.2033 0.6853 0.9872 0.045 Uiso 1 1 calc R . . C8A C 1.03688(14) 0.64057(9) 0.85523(18) 0.0326(4) Uani 1 1 d . . . N9 N 0.95970(12) 0.69638(8) 0.89234(17) 0.0323(3) Uani 1 1 d . . . C9A C 0.84512(15) 0.66875(9) 0.81038(18) 0.0306(3) Uani 1 1 d . . . C10 C 0.72984(14) 0.78260(9) 0.89878(18) 0.0317(3) Uani 1 1 d . . . H10 H 0.7951 0.8192 0.9342 0.038 Uiso 1 1 calc R . . C11 C 0.62963(13) 0.80249(9) 0.92578(18) 0.0340(4) Uani 1 1 d . . . H11 H 0.6203 0.8552 0.9712 0.041 Uiso 1 1 calc R . . C12 C 0.53098(13) 0.74165(9) 0.88454(18) 0.0347(3) Uani 1 1 d . . . C13 C 0.55047(17) 0.68242(10) 1.0461(2) 0.0442(4) Uani 1 1 d . . . H13A H 0.6264 0.6544 1.0698 0.066 Uiso 1 1 calc R . . H13B H 0.4865 0.6419 1.0155 0.066 Uiso 1 1 calc R . . H13C H 0.5509 0.7129 1.1566 0.066 Uiso 1 1 calc R . . C14 C 0.41076(15) 0.78179(11) 0.8324(2) 0.0442(4) Uani 1 1 d . . . H14A H 0.3491 0.7398 0.7926 0.066 Uiso 1 1 calc R . . H14B H 0.4023 0.8206 0.7313 0.066 Uiso 1 1 calc R . . H14C H 0.4029 0.8110 0.9396 0.066 Uiso 1 1 calc R . . C15 C 0.51700(16) 0.55414(10) 0.5038(2) 0.0462(4) Uani 1 1 d . . . H15A H 0.5309 0.5022 0.4502 0.069 Uiso 1 1 calc R . . H15B H 0.4746 0.5917 0.4045 0.069 Uiso 1 1 calc R . . H15C H 0.4695 0.5442 0.5846 0.069 Uiso 1 1 calc R . . H9 H 0.9820(16) 0.7333(12) 0.979(2) 0.049(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 C1 0.0399(8) 0.0241(7) 0.0255(6) -0.0006(6) 0.0133(6) -0.0021(7) C2 0.0387(9) 0.0265(7) 0.0255(6) 0.0001(6) 0.0102(6) 0.0005(7) O2 0.0366(6) 0.0326(5) 0.0290(5) -0.0054(4) 0.0096(4) -0.0014(5) C3 0.0473(10) 0.0257(8) 0.0275(7) -0.0035(6) 0.0104(6) -0.0053(7) C4 0.0505(10) 0.0254(8) 0.0306(7) -0.0060(6) 0.0144(7) -0.0010(8) C4A 0.0456(9) 0.0264(8) 0.0268(7) -0.0009(6) 0.0147(6) -0.0008(7) C4B 0.0468(9) 0.0293(8) 0.0276(7) 0.0027(6) 0.0178(6) 0.0047(7) C5 0.0555(12) 0.0323(8) 0.0348(8) -0.0009(6) 0.0198(8) 0.0039(8) C6 0.0587(12) 0.0376(9) 0.0448(9) 0.0032(7) 0.0282(8) 0.0113(9) C7 0.0447(11) 0.0451(10) 0.0440(9) 0.0091(7) 0.0211(8) 0.0075(8) C8 0.0431(11) 0.0373(8) 0.0344(7) 0.0015(7) 0.0160(7) 0.0011(8) C8A 0.0457(10) 0.0284(8) 0.0291(7) 0.0034(6) 0.0194(7) 0.0033(7) N9 0.0387(8) 0.0279(6) 0.0327(6) -0.0065(5) 0.0151(5) -0.0029(6) C9A 0.0420(9) 0.0249(7) 0.0267(7) -0.0003(5) 0.0135(6) -0.0027(7) C10 0.0395(9) 0.0254(7) 0.0299(7) -0.0036(6) 0.0107(6) -0.0029(7) C11 0.0455(10) 0.0262(7) 0.0296(7) -0.0052(6) 0.0112(6) 0.0002(7) C12 0.0427(9) 0.0345(8) 0.0290(7) -0.0064(6) 0.0143(6) -0.0016(8) C13 0.0596(11) 0.0410(10) 0.0348(8) -0.0020(7) 0.0192(7) -0.0088(9) C14 0.0407(10) 0.0518(11) 0.0427(8) -0.0115(8) 0.0168(7) -0.0007(8) C15 0.0494(11) 0.0377(10) 0.0465(9) -0.0148(8) 0.0087(7) -0.0067(8) _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 C2 1.390(2) . ? C1 C9A 1.398(2) . ? C1 C10 1.4563(19) . ? C2 O2 1.3821(17) . ? C2 C3 1.4086(19) . ? O2 C12 1.4809(16) . ? C3 C4 1.387(2) . ? C3 C15 1.504(2) . ? C4 C4A 1.394(2) . ? C4 H4 0.9500 . ? C4A C9A 1.410(2) . ? C4A C4B 1.443(2) . ? C4B C5 1.392(2) . ? C4B C8A 1.410(2) . ? C5 C6 1.375(2) . ? C5 H5 0.9500 . ? C6 C7 1.398(3) . ? C6 H6 0.9500 . ? C7 C8 1.385(2) . ? C7 H7 0.9500 . ? C8 C8A 1.389(2) . ? C8 H8 0.9500 . ? C8A N9 1.3913(19) . ? N9 C9A 1.384(2) . ? N9 H9 0.874(19) . ? C10 C11 1.321(2) . ? C10 H10 0.9500 . ? C11 C12 1.496(2) . ? C11 H11 0.9500 . ? C12 C14 1.511(2) . ? C12 C13 1.527(2) . ? C13 H13A 0.9800 . ? C13 H13B 0.9800 . ? C13 H13C 0.9800 . ? C14 H14A 0.9800 . ? C14 H14B 0.9800 . ? C14 H14C 0.9800 . ? C15 H15A 0.9800 . ? C15 H15B 0.9800 . ? C15 H15C 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 C2 C1 C9A 116.04(13) . . ? C2 C1 C10 118.52(14) . . ? C9A C1 C10 125.35(15) . . ? O2 C2 C1 119.09(12) . . ? O2 C2 C3 117.04(13) . . ? C1 C2 C3 123.70(14) . . ? C2 O2 C12 115.77(10) . . ? C4 C3 C2 117.93(14) . . ? C4 C3 C15 121.95(13) . . ? C2 C3 C15 120.10(14) . . ? C3 C4 C4A 120.90(13) . . ? C3 C4 H4 119.5 . . ? C4A C4 H4 119.5 . . ? C4 C4A C9A 118.86(15) . . ? C4 C4A C4B 134.54(13) . . ? C9A C4A C4B 106.58(14) . . ? C5 C4B C8A 118.80(15) . . ? C5 C4B C4A 134.37(15) . . ? C8A C4B C4A 106.81(12) . . ? C6 C5 C4B 119.48(15) . . ? C6 C5 H5 120.3 . . ? C4B C5 H5 120.3 . . ? C5 C6 C7 120.76(16) . . ? C5 C6 H6 119.6 . . ? C7 C6 H6 119.6 . . ? C8 C7 C6 121.46(17) . . ? C8 C7 H7 119.3 . . ? C6 C7 H7 119.3 . . ? C7 C8 C8A 117.14(15) . . ? C7 C8 H8 121.4 . . ? C8A C8 H8 121.4 . . ? C8 C8A N9 128.82(14) . . ? C8 C8A C4B 122.36(14) . . ? N9 C8A C4B 108.82(14) . . ? C9A N9 C8A 108.56(13) . . ? C9A N9 H9 125.6(12) . . ? C8A N9 H9 123.4(12) . . ? N9 C9A C1 128.46(14) . . ? N9 C9A C4A 109.18(14) . . ? C1 C9A C4A 122.36(15) . . ? C11 C10 C1 119.61(15) . . ? C11 C10 H10 120.2 . . ? C1 C10 H10 120.2 . . ? C10 C11 C12 119.78(13) . . ? C10 C11 H11 120.1 . . ? C12 C11 H11 120.1 . . ? O2 C12 C11 108.87(11) . . ? O2 C12 C14 104.79(11) . . ? C11 C12 C14 112.61(13) . . ? O2 C12 C13 108.18(12) . . ? C11 C12 C13 110.42(13) . . ? C14 C12 C13 111.70(14) . . ? C12 C13 H13A 109.5 . . ? C12 C13 H13B 109.5 . . ? H13A C13 H13B 109.5 . . ? C12 C13 H13C 109.5 . . ? H13A C13 H13C 109.5 . . ? H13B C13 H13C 109.5 . . ? C12 C14 H14A 109.5 . . ? C12 C14 H14B 109.5 . . ? H14A C14 H14B 109.5 . . ? C12 C14 H14C 109.5 . . ? H14A C14 H14C 109.5 . . ? H14B C14 H14C 109.5 . . ? C3 C15 H15A 109.5 . . ? C3 C15 H15B 109.5 . . ? H15A C15 H15B 109.5 . . ? C3 C15 H15C 109.5 . . ? H15A C15 H15C 109.5 . . ? H15B C15 H15C 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 C9A C1 C2 O2 179.94(12) . . . . ? C10 C1 C2 O2 -3.41(19) . . . . ? C9A C1 C2 C3 -4.92(19) . . . . ? C10 C1 C2 C3 171.73(13) . . . . ? C1 C2 O2 C12 -30.58(17) . . . . ? C3 C2 O2 C12 153.96(12) . . . . ? O2 C2 C3 C4 179.59(12) . . . . ? C1 C2 C3 C4 4.4(2) . . . . ? O2 C2 C3 C15 0.81(19) . . . . ? C1 C2 C3 C15 -174.42(14) . . . . ? C2 C3 C4 C4A -0.4(2) . . . . ? C15 C3 C4 C4A 178.39(14) . . . . ? C3 C4 C4A C9A -2.6(2) . . . . ? C3 C4 C4A C4B 178.85(14) . . . . ? C4 C4A C4B C5 -3.5(3) . . . . ? C9A C4A C4B C5 177.82(15) . . . . ? C4 C4A C4B C8A 178.18(15) . . . . ? C9A C4A C4B C8A -0.48(14) . . . . ? C8A C4B C5 C6 -0.3(2) . . . . ? C4A C4B C5 C6 -178.48(16) . . . . ? C4B C5 C6 C7 -0.5(2) . . . . ? C5 C6 C7 C8 0.8(2) . . . . ? C6 C7 C8 C8A -0.3(2) . . . . ? C7 C8 C8A N9 179.82(13) . . . . ? C7 C8 C8A C4B -0.6(2) . . . . ? C5 C4B C8A C8 0.9(2) . . . . ? C4A C4B C8A C8 179.53(12) . . . . ? C5 C4B C8A N9 -179.42(12) . . . . ? C4A C4B C8A N9 -0.81(15) . . . . ? C8 C8A N9 C9A -178.55(14) . . . . ? C4B C8A N9 C9A 1.83(15) . . . . ? C8A N9 C9A C1 178.64(13) . . . . ? C8A N9 C9A C4A -2.14(15) . . . . ? C2 C1 C9A N9 -179.21(13) . . . . ? C10 C1 C9A N9 4.4(2) . . . . ? C2 C1 C9A C4A 1.66(18) . . . . ? C10 C1 C9A C4A -174.72(13) . . . . ? C4 C4A C9A N9 -177.30(13) . . . . ? C4B C4A C9A N9 1.61(14) . . . . ? C4 C4A C9A C1 1.97(19) . . . . ? C4B C4A C9A C1 -179.12(13) . . . . ? C2 C1 C10 C11 16.8(2) . . . . ? C9A C1 C10 C11 -166.90(13) . . . . ? C1 C10 C11 C12 5.2(2) . . . . ? C2 O2 C12 C11 48.78(15) . . . . ? C2 O2 C12 C14 169.47(12) . . . . ? C2 O2 C12 C13 -71.24(16) . . . . ? C10 C11 C12 O2 -36.35(17) . . . . ? C10 C11 C12 C14 -152.11(13) . . . . ? C10 C11 C12 C13 82.28(16) . . . . ? _diffrn_measured_fraction_theta_max 0.998 _diffrn_reflns_theta_full 28.00 _diffrn_measured_fraction_theta_full 0.998 _refine_diff_density_max 0.127 _refine_diff_density_min -0.212 _refine_diff_density_rms 0.041 _chemical_compound_source synthesis