#------------------------------------------------------------------------------ #$Date: 2011-09-10 06:16:28 +0300 (Sat, 10 Sep 2011) $ #$Revision: 25271 $ #$URL: file:///home/coder/svn-repositories/cod/cif/2/2006981.cif $ #------------------------------------------------------------------------------ # # This file is available in the Crystallography Open Database (COD), # http://www.crystallography.net/. The original data for this entry # were provided by IUCr Journals, http://journals.iucr.org/. # # The file may be used within the scientific community so long as # proper attribution is given to the journal article from which the # data were obtained. # data_2006981 loop_ _publ_author_name 'Nastopoulos, V.' 'Athanassopoulos, C.' 'Papaioannou, D.' 'Francis, G. W.' 'Kavounis, C.' _publ_section_title ; (S),(E)-5-Methoxycarbonyl-3-triphenylmethylaminohex-4-en-4-olide ; _journal_issue 2 _journal_name_full 'Acta Crystallographica Section C' _journal_page_first 267 _journal_page_last 269 _journal_volume 54 _journal_year 1998 _chemical_formula_moiety 'C27 H25 N O4' _chemical_formula_sum 'C27 H25 N O4' _chemical_formula_weight 427.48 _chemical_name_systematic (S),(E)-5-Methoxycarbonyl-3-triphenylmethylaminohex-4-en-4-olide _space_group_IT_number 4 _symmetry_cell_setting monoclinic _symmetry_space_group_name_Hall 'P 2yb' _symmetry_space_group_name_H-M 'P 1 21 1' _cell_angle_alpha 90.00 _cell_angle_beta 100.89(6) _cell_angle_gamma 90.00 _cell_formula_units_Z 2 _cell_length_a 10.880(4) _cell_length_b 8.875(3) _cell_length_c 11.845(5) _cell_measurement_reflns_used 32 _cell_measurement_temperature 293(2) _cell_measurement_theta_max 19.6 _cell_measurement_theta_min 10.4 _cell_volume 1123.2(8) _computing_cell_refinement DIF4 _computing_data_collection 'DIF4 (Stoe & Cie, 1988a)' _computing_data_reduction 'REDU4 (Stoe & Cie, 1988b)' _computing_molecular_graphics 'PLATON (Spek, 1990)' _computing_publication_material SHELXL93 _computing_structure_refinement 'SHELXL93 (Sheldrick, 1993)' _computing_structure_solution 'SHELXS86 (Sheldrick, 1990)' _diffrn_ambient_temperature 293(2) _diffrn_measurement_device_type 'Philips PW1100 diffractometer updated by Stoe' _diffrn_measurement_method \w-2\q _diffrn_radiation_monochromator graphite _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_type MoK\a _diffrn_radiation_wavelength 0.71069 _diffrn_reflns_av_R_equivalents 0.024 _diffrn_reflns_av_sigmaI/netI 0.0206 _diffrn_reflns_limit_h_max 15 _diffrn_reflns_limit_h_min -15 _diffrn_reflns_limit_k_max 12 _diffrn_reflns_limit_k_min 0 _diffrn_reflns_limit_l_max 16 _diffrn_reflns_limit_l_min 0 _diffrn_reflns_number 3477 _diffrn_reflns_theta_max 30.03 _diffrn_reflns_theta_min 1.75 _diffrn_standards_decay_% 2.5 _diffrn_standards_interval_time 120 _diffrn_standards_number 3 _exptl_absorpt_coefficient_mu 0.085 _exptl_absorpt_correction_type none _exptl_crystal_colour colourless _exptl_crystal_density_diffrn 1.266 _exptl_crystal_density_method 'not measured' _exptl_crystal_description prism _exptl_crystal_F_000 452 _exptl_crystal_size_max 0.60 _exptl_crystal_size_mid 0.40 _exptl_crystal_size_min 0.30 _refine_diff_density_max 0.332 _refine_diff_density_min -0.487 _refine_ls_extinction_method none _refine_ls_goodness_of_fit_all 1.079 _refine_ls_goodness_of_fit_ref 1.153 _refine_ls_hydrogen_treatment 'H atoms treated by a mixture of independent and constrained refinement' _refine_ls_matrix_type full _refine_ls_number_parameters 294 _refine_ls_number_reflns 3476 _refine_ls_number_restraints 1 _refine_ls_R_factor_all 0.084 _refine_ls_R_factor_gt 0.061 _refine_ls_shift/su_max 0.001 _refine_ls_shift/su_mean 0.000 _refine_ls_structure_factor_coef Fsqd _refine_ls_weighting_details 'calc w = 1/[\s^2^(Fo^2^)+(0.1088P)^2^] where P = (Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_all 0.158 _refine_ls_wR_factor_ref 0.142 _reflns_number_gt 2542 _reflns_number_total 3476 _reflns_threshold_expression I>2\s(I) _[local]_cod_data_source_file ab1492.cif _[local]_cod_data_source_block ENES _[local]_cod_cif_authors_sg_H-M 'P 21' _cod_original_cell_volume 1123.2(7) _cod_database_code 2006981 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y+1/2, -z' loop_ _atom_site_label _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_calc_flag _atom_site_refinement_flags _atom_site_occupancy _atom_site_type_symbol C1 0.2235(3) 0.1008(4) 0.5924(3) 0.0586(7) Uani d . 1 C C2 0.1538(2) 0.0637(3) 0.4763(2) 0.0491(6) Uani d . 1 C C3 0.1575(2) 0.2071(3) 0.4058(2) 0.0412(5) Uani d . 1 C C4 0.1923(2) 0.3251(3) 0.4990(2) 0.0459(5) Uani d . 1 C O1 0.2421(2) 0.2545(3) 0.6013(2) 0.0576(5) Uani d . 1 O O2 0.2599(3) 0.0234(4) 0.6731(2) 0.0907(9) Uani d . 1 O C5 0.1878(3) 0.4760(3) 0.4983(2) 0.0515(6) Uani d . 1 C C6 0.2417(4) 0.5685(5) 0.6035(3) 0.0737(9) Uani d . 1 C C7 0.1219(3) 0.5633(4) 0.3993(3) 0.0565(7) Uani d . 1 C O3 0.0941(3) 0.6937(3) 0.4063(2) 0.0849(8) Uani d . 1 O O4 0.0909(2) 0.4855(3) 0.3019(2) 0.0683(6) Uani d . 1 O C8 0.0125(4) 0.5623(5) 0.2067(3) 0.0822(11) Uani d . 1 C N1 0.2611(2) 0.2077(3) 0.3404(2) 0.0403(4) Uani d . 1 N C9 0.2536(2) 0.1029(3) 0.2405(2) 0.0371(4) Uani d . 1 C C10 0.3155(2) -0.0495(3) 0.2788(2) 0.0385(4) Uani d . 1 C C11 0.2980(2) -0.1735(3) 0.2059(2) 0.0474(5) Uani d . 1 C C12 0.3574(3) -0.3101(4) 0.2369(3) 0.0570(6) Uani d . 1 C C13 0.4379(3) -0.3237(4) 0.3418(3) 0.0596(7) Uani d . 1 C C14 0.4593(3) -0.2004(4) 0.4126(2) 0.0599(7) Uani d . 1 C C15 0.3995(2) -0.0638(3) 0.3823(2) 0.0475(5) Uani d . 1 C C16 0.3357(2) 0.1716(3) 0.1600(2) 0.0441(5) Uani d . 1 C C17 0.3108(3) 0.1426(4) 0.0420(2) 0.0566(7) Uani d . 1 C C18 0.3874(4) 0.2027(5) -0.0283(3) 0.0721(9) Uani d . 1 C C19 0.4865(4) 0.2922(5) 0.0158(4) 0.0819(11) Uani d . 1 C C20 0.5159(3) 0.3176(5) 0.1326(3) 0.0762(10) Uani d . 1 C C21 0.4400(3) 0.2567(4) 0.2041(2) 0.0577(7) Uani d . 1 C C22 0.1156(2) 0.0872(3) 0.1797(2) 0.0415(5) Uani d . 1 C C23 0.0399(2) -0.0297(3) 0.2035(2) 0.0497(6) Uani d . 1 C C24 -0.0881(3) -0.0316(5) 0.1564(3) 0.0664(8) Uani d . 1 C C25 -0.1415(3) 0.0847(6) 0.0875(3) 0.0748(10) Uani d . 1 C C26 -0.0682(3) 0.2025(5) 0.0657(3) 0.0759(10) Uani d . 1 C C27 0.0603(3) 0.2055(4) 0.1106(2) 0.0564(6) Uani d . 1 C H2A 0.0681 0.0360 0.4790 0.059 Uiso calc R 1 H H2B 0.1933 -0.0193 0.4435 0.059 Uiso calc R 1 H H3 0.0765 0.2284 0.3563 0.049 Uiso calc R 1 H H6A 0.1758 0.624 0.6283 0.111 Uiso calc R 1 H H6B 0.303 0.638 0.5848 0.111 Uiso calc R 1 H H6C 0.281 0.5027 0.6641 0.111 Uiso calc R 1 H H8A -0.0039 0.4963 0.1413 0.123 Uiso calc R 1 H H8B 0.0545 0.6510 0.1875 0.123 Uiso calc R 1 H H8C -0.0652 0.5902 0.2282 0.123 Uiso calc R 1 H H1 0.271(3) 0.303(5) 0.312(3) 0.062(9) Uiso d . 1 H H11 0.2453 -0.1648 0.1346 0.057 Uiso calc R 1 H H12 0.3431 -0.3922 0.1872 0.068 Uiso calc R 1 H H13 0.4768 -0.4151 0.3639 0.071 Uiso calc R 1 H H14 0.5150 -0.2083 0.4824 0.072 Uiso calc R 1 H H15 0.4158 0.0184 0.4315 0.057 Uiso calc R 1 H H17 0.2428 0.0828 0.0104 0.068 Uiso calc R 1 H H18 0.3706 0.1814 -0.1066 0.087 Uiso calc R 1 H H19 0.5342 0.3360 -0.0328 0.098 Uiso calc R 1 H H20 0.5857 0.3748 0.1637 0.091 Uiso calc R 1 H H21 0.4601 0.2739 0.2829 0.069 Uiso calc R 1 H H23 0.0747 -0.1078 0.2514 0.060 Uiso calc R 1 H H24 -0.1373 -0.1119 0.1719 0.080 Uiso calc R 1 H H25 -0.2265 0.0833 0.0559 0.090 Uiso calc R 1 H H26 -0.1045 0.2821 0.0202 0.091 Uiso calc R 1 H H27 0.1088 0.2861 0.0943 0.068 Uiso calc R 1 H loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_12 _atom_site_aniso_U_13 _atom_site_aniso_U_23 _atom_site_aniso_type_symbol C1 0.0593(15) 0.066(2) 0.0510(14) 0.0008(14) 0.0126(12) 0.0071(14) C C2 0.0525(13) 0.0502(13) 0.0485(13) -0.0035(11) 0.0194(10) 0.0028(11) C C3 0.0411(10) 0.0444(11) 0.0394(10) -0.0007(9) 0.0114(8) -0.0008(9) C C4 0.0469(12) 0.0518(13) 0.0417(11) 0.0006(11) 0.0152(9) -0.0040(10) C O1 0.0640(11) 0.0677(13) 0.0403(9) -0.0011(10) 0.0075(8) -0.0021(9) O O2 0.121(2) 0.085(2) 0.0595(14) 0.003(2) -0.0005(14) 0.0258(13) O C5 0.0559(14) 0.0511(14) 0.0527(14) -0.0047(11) 0.0232(11) -0.0076(12) C C6 0.095(2) 0.064(2) 0.067(2) -0.010(2) 0.027(2) -0.021(2) C C7 0.0634(15) 0.0480(14) 0.066(2) -0.0033(13) 0.0311(13) 0.0023(13) C O3 0.132(2) 0.0457(12) 0.086(2) 0.0108(14) 0.043(2) 0.0035(12) O O4 0.0863(14) 0.0507(11) 0.0651(13) 0.0072(11) 0.0074(11) 0.0025(10) O C8 0.102(3) 0.061(2) 0.076(2) 0.007(2) -0.003(2) 0.011(2) C N1 0.0443(9) 0.0410(10) 0.0370(8) -0.0015(8) 0.0116(7) -0.0025(8) N C9 0.0399(9) 0.0381(10) 0.0331(9) 0.0007(8) 0.0067(7) 0.0006(8) C C10 0.0369(9) 0.0412(11) 0.0377(10) 0.0022(9) 0.0081(8) 0.0029(9) C C11 0.0503(12) 0.0466(13) 0.0422(11) 0.0037(11) 0.0008(9) -0.0046(10) C C12 0.0613(15) 0.0478(14) 0.0602(15) 0.0076(13) 0.0069(12) -0.0083(12) C C13 0.0584(15) 0.053(2) 0.066(2) 0.0133(13) 0.0074(12) 0.0053(14) C C14 0.0542(14) 0.067(2) 0.0531(15) 0.0149(14) -0.0026(11) 0.0069(13) C C15 0.0457(11) 0.0519(14) 0.0418(11) 0.0035(11) 0.0004(9) -0.0035(10) C C16 0.0529(12) 0.0428(13) 0.0391(10) -0.0008(10) 0.0151(9) 0.0018(9) C C17 0.071(2) 0.060(2) 0.0421(12) -0.0048(14) 0.0190(11) -0.0032(12) C C18 0.095(2) 0.080(2) 0.0495(14) 0.001(2) 0.0350(15) 0.002(2) C C19 0.105(3) 0.079(3) 0.078(2) -0.019(2) 0.059(2) -0.003(2) C C20 0.080(2) 0.080(2) 0.078(2) -0.030(2) 0.039(2) -0.014(2) C C21 0.0620(15) 0.063(2) 0.0534(14) -0.0138(13) 0.0255(11) -0.0078(13) C C22 0.0416(10) 0.0475(12) 0.0336(9) 0.0042(9) 0.0028(7) -0.0011(9) C C23 0.0440(11) 0.0513(14) 0.0522(14) -0.0006(11) 0.0052(9) -0.0035(11) C C24 0.0446(13) 0.080(2) 0.072(2) -0.0060(14) 0.0038(12) -0.015(2) C C25 0.0454(13) 0.101(3) 0.070(2) 0.013(2) -0.0102(12) -0.018(2) C C26 0.069(2) 0.087(2) 0.060(2) 0.022(2) -0.0172(14) 0.003(2) C C27 0.0600(14) 0.061(2) 0.0452(12) 0.0101(14) 0.0013(10) 0.0089(13) C 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' N N 0.0061 0.0033 '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_publ_flag O2 C1 O1 119.3(3) yes O2 C1 C2 131.1(3) yes O1 C1 C2 109.5(3) yes C1 C2 C3 105.2(2) yes C1 C2 H2A 110.7(2) ? C3 C2 H2A 110.71(13) ? C1 C2 H2B 110.7(2) ? C3 C2 H2B 110.71(14) ? H2A C2 H2B 108.8 ? N1 C3 C4 105.5(2) ? N1 C3 C2 112.9(2) ? C4 C3 C2 101.9(2) yes N1 C3 H3 111.97(12) ? C4 C3 H3 111.97(14) ? C2 C3 H3 111.97(13) ? C5 C4 O1 117.8(3) ? C5 C4 C3 133.0(3) ? O1 C4 C3 109.1(2) yes C1 O1 C4 110.7(2) yes C4 C5 C7 122.8(3) ? C4 C5 C6 121.9(3) ? C7 C5 C6 115.1(3) ? C5 C6 H6A 109.5(2) ? C5 C6 H6B 109.5(2) ? H6A C6 H6B 109.5 ? C5 C6 H6C 109.5(2) ? H6A C6 H6C 109.5 ? H6B C6 H6C 109.5 ? O3 C7 O4 122.1(3) ? O3 C7 C5 122.8(3) ? O4 C7 C5 115.0(3) ? C7 O4 C8 116.5(3) ? O4 C8 H8A 109.5(2) ? O4 C8 H8B 109.5(2) ? H8A C8 H8B 109.5 ? O4 C8 H8C 109.5(2) ? H8A C8 H8C 109.5 ? H8B C8 H8C 109.5 ? C3 N1 C9 118.5(2) yes C3 N1 H1 111.(2) ? C9 N1 H1 106.(2) ? N1 C9 C10 110.9(2) ? N1 C9 C22 109.2(2) ? C10 C9 C22 113.0(2) ? N1 C9 C16 106.9(2) ? C10 C9 C16 104.8(2) ? C22 C9 C16 111.8(2) ? C15 C10 C11 117.8(2) ? C15 C10 C9 121.3(2) ? C11 C10 C9 120.7(2) ? C10 C11 C12 121.6(2) ? C10 C11 H11 119.20(14) ? C12 C11 H11 119.2(2) ? C13 C12 C11 119.8(3) ? C13 C12 H12 120.1(2) ? C11 C12 H12 120.1(2) ? C14 C13 C12 119.1(3) ? C14 C13 H13 120.5(2) ? C12 C13 H13 120.5(2) ? C13 C14 C15 121.3(2) ? C13 C14 H14 119.4(2) ? C15 C14 H14 119.4(2) ? C10 C15 C14 120.4(2) ? C10 C15 H15 119.8(2) ? C14 C15 H15 119.8(2) ? C21 C16 C17 118.0(2) ? C21 C16 C9 120.7(2) ? C17 C16 C9 121.2(2) ? C18 C17 C16 120.2(3) ? C18 C17 H17 119.9(2) ? C16 C17 H17 119.9(2) ? C19 C18 C17 121.0(3) ? C19 C18 H18 119.5(2) ? C17 C18 H18 119.5(2) ? C18 C19 C20 119.8(3) ? C18 C19 H19 120.1(2) ? C20 C19 H19 120.1(2) ? C19 C20 C21 119.5(3) ? C19 C20 H20 120.2(2) ? C21 C20 H20 120.2(2) ? C16 C21 C20 121.3(3) ? C16 C21 H21 119.35(15) ? C20 C21 H21 119.4(2) ? C23 C22 C27 118.5(2) ? C23 C22 C9 122.4(2) ? C27 C22 C9 118.6(2) ? C22 C23 C24 120.8(3) ? C22 C23 H23 119.59(14) ? C24 C23 H23 119.6(2) ? C25 C24 C23 120.3(3) ? C25 C24 H24 119.8(2) ? C23 C24 H24 119.8(2) ? C26 C25 C24 119.3(3) ? C26 C25 H25 120.4(2) ? C24 C25 H25 120.4(2) ? C25 C26 C27 121.3(3) ? C25 C26 H26 119.4(2) ? C27 C26 H26 119.4(2) ? C22 C27 C26 119.8(3) ? C22 C27 H27 120.1(2) ? C26 C27 H27 120.1(2) ? loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_publ_flag C1 O2 1.183(4) yes C1 O1 1.380(4) yes C1 C2 1.476(4) yes C2 C3 1.527(4) yes C2 H2A 0.97 ? C2 H2B 0.97 ? C3 N1 1.484(3) yes C3 C4 1.517(4) yes C3 H3 0.98 ? C4 C5 1.340(4) yes C4 O1 1.382(3) yes C5 C7 1.473(5) yes C5 C6 1.515(5) yes C6 H6A 0.96 ? C6 H6B 0.96 ? C6 H6C 0.96 ? C7 O3 1.203(4) ? C7 O4 1.332(4) ? O4 C8 1.449(4) ? C8 H8A 0.96 ? C8 H8B 0.96 ? C8 H8C 0.96 ? N1 C9 1.495(3) ? N1 H1 0.93(4) ? C9 C10 1.541(3) ? C9 C22 1.544(3) ? C9 C16 1.550(3) ? C10 C15 1.389(3) ? C10 C11 1.390(4) ? C11 C12 1.391(4) ? C11 H11 0.93 ? C12 C13 1.383(4) ? C12 H12 0.93 ? C13 C14 1.372(5) ? C13 H13 0.93 ? C14 C15 1.391(4) ? C14 H14 0.93 ? C15 H15 0.93 ? C16 C21 1.381(4) ? C16 C17 1.396(3) ? C17 C18 1.391(4) ? C17 H17 0.93 ? C18 C19 1.361(6) ? C18 H18 0.93 ? C19 C20 1.379(5) ? C19 H19 0.93 ? C20 C21 1.398(4) ? C20 H20 0.93 ? C21 H21 0.93 ? C22 C23 1.386(4) ? C22 C27 1.396(4) ? C23 C24 1.400(4) ? C23 H23 0.93 ? C24 C25 1.375(6) ? C24 H24 0.93 ? C25 C26 1.369(7) ? C25 H25 0.93 ? C26 C27 1.399(4) ? C26 H26 0.93 ? C27 H27 0.93 ? 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_publ_flag O2 C1 C2 C3 -169.3(3) ? O1 C1 C2 C3 12.6(3) ? C1 C2 C3 N1 94.9(2) yes C1 C2 C3 C4 -17.8(2) yes N1 C3 C4 C5 77.0(4) yes C2 C3 C4 C5 -164.9(3) ? N1 C3 C4 O1 -100.2(2) ? C2 C3 C4 O1 18.0(2) ? O2 C1 O1 C4 -179.5(3) ? C2 C1 O1 C4 -1.1(3) ? C5 C4 O1 C1 171.2(3) ? C3 C4 O1 C1 -11.2(3) ? O1 C4 C5 C7 -171.6(2) ? C3 C4 C5 C7 11.5(5) ? O1 C4 C5 C6 3.4(4) ? C3 C4 C5 C6 -173.5(3) yes C4 C5 C7 O3 163.3(3) yes C6 C5 C7 O3 -12.0(4) ? C4 C5 C7 O4 -14.3(4) ? C6 C5 C7 O4 170.4(3) ? O3 C7 O4 C8 -5.1(5) ? C5 C7 O4 C8 172.5(3) ? C4 C3 N1 C9 -179.4(2) yes C2 C3 N1 C9 70.2(3) ? C3 N1 C9 C10 -90.4(2) ? C3 N1 C9 C22 34.7(3) ? C3 N1 C9 C16 155.9(2) ? N1 C9 C10 C15 -19.0(3) ? C22 C9 C10 C15 -142.0(2) ? C16 C9 C10 C15 96.0(2) ? N1 C9 C10 C11 167.1(2) ? C22 C9 C10 C11 44.1(3) ? C16 C9 C10 C11 -77.9(2) ? C15 C10 C11 C12 3.1(4) ? C9 C10 C11 C12 177.2(2) ? C10 C11 C12 C13 -1.2(4) ? C11 C12 C13 C14 -1.2(5) ? C12 C13 C14 C15 1.7(5) ? C11 C10 C15 C14 -2.6(4) ? C9 C10 C15 C14 -176.7(2) ? C13 C14 C15 C10 0.3(4) ? N1 C9 C16 C21 30.9(3) ? C10 C9 C16 C21 -86.9(3) ? C22 C9 C16 C21 150.3(3) ? N1 C9 C16 C17 -152.8(2) ? C10 C9 C16 C17 89.4(3) ? C22 C9 C16 C17 -33.4(3) ? C21 C16 C17 C18 -2.1(5) ? C9 C16 C17 C18 -178.6(3) ? C16 C17 C18 C19 -0.9(6) ? C17 C18 C19 C20 3.5(7) ? C18 C19 C20 C21 -3.0(7) ? C17 C16 C21 C20 2.6(5) ? C9 C16 C21 C20 179.1(3) ? C19 C20 C21 C16 -0.1(6) ? N1 C9 C22 C23 -95.4(3) ? C10 C9 C22 C23 28.6(3) ? C16 C9 C22 C23 146.6(2) ? N1 C9 C22 C27 75.5(3) ? C10 C9 C22 C27 -160.5(2) ? C16 C9 C22 C27 -42.5(3) ? C27 C22 C23 C24 2.0(4) ? C9 C22 C23 C24 172.9(2) ? C22 C23 C24 C25 -1.4(5) ? C23 C24 C25 C26 -0.2(5) ? C24 C25 C26 C27 1.2(6) ? C23 C22 C27 C26 -1.0(4) ? C9 C22 C27 C26 -172.3(3) ? C25 C26 C27 C22 -0.6(5) ?