#------------------------------------------------------------------------------ #$Date: 2015-01-12 13:22:06 +0200 (Mon, 12 Jan 2015) $ #$Revision: 129545 $ #$URL: file:///home/coder/svn-repositories/cod/cif/7/11/63/7116328.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_7116328 loop_ _publ_author_name 'Rumpa Pal' 'Govindappa Nagendra' 'M. Samarasimhareddy' 'Vommina V. Sureshbabu' 'Tayur N. Guru Row' _publ_section_title ; Observation of a reversible isomorphous phase transition and an interplay of 'sigma-holes' and 'pi-holes' in Fmoc-Leu-psi[CH2-NCS] ; _journal_name_full Chem.Commun. _journal_page_first 933 _journal_paper_doi 10.1039/C4cc08751H _journal_volume 51 _journal_year 2015 _chemical_absolute_configuration unk _chemical_compound_source 'see text' _chemical_formula_moiety 'C21 H22 N2 O2 S' _chemical_formula_sum 'C21 H22 N2 O2 S' _chemical_formula_weight 366.48 _chemical_name_systematic ; ; _space_group_IT_number 4 _symmetry_cell_setting monoclinic _symmetry_Int_Tables_number 4 _symmetry_space_group_name_Hall 'P 2yb' _symmetry_space_group_name_H-M 'P 1 21 1' _atom_sites_solution_hydrogens geom _audit_update_record ; 2014-11-01 deposited with the CCDC. 2014-11-24 downloaded from the CCDC. ; _cell_angle_alpha 90 _cell_angle_beta 99.174(4) _cell_angle_gamma 90 _cell_formula_units_Z 2 _cell_length_a 4.9807(2) _cell_length_b 15.9306(6) _cell_length_c 12.0456(5) _cell_measurement_reflns_used 3702 _cell_measurement_temperature 100(2) _cell_measurement_theta_max 26.0 _cell_measurement_theta_min 2.6 _cell_volume 943.54(7) _computing_cell_refinement ; CrysAlisPro, Agilent Technologies, Version 1.171.37.31 (release 14-01-2014 CrysAlis171 .NET) (compiled Jan 14 2014,18:38:05) ; _computing_data_collection ; CrysAlisPro, Agilent Technologies, Version 1.171.37.31 (release 14-01-2014 CrysAlis171 .NET) (compiled Jan 14 2014,18:38:05) ; _computing_data_reduction ; CrysAlisPro, Agilent Technologies, Version 1.171.37.31 (release 14-01-2014 CrysAlis171 .NET) (compiled Jan 14 2014,18:38:05) ; _computing_publication_material 'PLATON (Spek, 2003)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1997)' _diffrn_ambient_temperature 100(2) _diffrn_detector_area_resol_mean 18.4 _diffrn_measured_fraction_theta_full 0.999 _diffrn_measured_fraction_theta_max 0.999 _diffrn_measurement_device_type 'four-circle diffractometer' _diffrn_measurement_method '\w scans' _diffrn_radiation_monochromator graphite _diffrn_radiation_probe x-ray _diffrn_radiation_source 'Rotating Anode' _diffrn_radiation_type MoK\a _diffrn_radiation_wavelength 0.71073 _diffrn_reflns_av_R_equivalents 0.0306 _diffrn_reflns_limit_h_max 6 _diffrn_reflns_limit_h_min -6 _diffrn_reflns_limit_k_max 19 _diffrn_reflns_limit_k_min -19 _diffrn_reflns_limit_l_max 14 _diffrn_reflns_limit_l_min -10 _diffrn_reflns_number 6646 _diffrn_reflns_reduction_process ; ; _diffrn_reflns_theta_full 25.24 _diffrn_reflns_theta_max 26.00 _diffrn_reflns_theta_min 2.56 _exptl_absorpt_coefficient_mu 0.189 _exptl_absorpt_correction_T_max 0.996 _exptl_absorpt_correction_T_min 0.981 _exptl_absorpt_correction_type analytical _exptl_absorpt_process_details ; CrysAlisPro, Agilent Technologies, Version 1.171.37.31 (release 14-01-2014 CrysAlis171 .NET) (compiled Jan 14 2014,18:38:05) Analytical numeric absorption correction using a multifaceted crystal model based on expressions derived by R.C. Clark & J.S. Reid. (Clark, R. C. & Reid, J. S. (1995). Acta Cryst. A51, 887-897) Empirical absorption correction using spherical harmonics, implemented in SCALE3 ABSPACK scaling algorithm. ; _exptl_crystal_colour colourless _exptl_crystal_density_diffrn 1.290 _exptl_crystal_density_method 'not measured' _exptl_crystal_description plate _exptl_crystal_F_000 388 _exptl_crystal_size_max 0.257 _exptl_crystal_size_mid 0.239 _exptl_crystal_size_min 0.048 _refine_diff_density_max 0.189 _refine_diff_density_min -0.206 _refine_diff_density_rms 0.037 _refine_ls_abs_structure_details 'Flack H.D. (1983), Acta Cryst. A39, 876-881' _refine_ls_abs_structure_Flack -0.06(6) _refine_ls_extinction_method none _refine_ls_goodness_of_fit_ref 1.034 _refine_ls_hydrogen_treatment constr _refine_ls_matrix_type full _refine_ls_number_parameters 237 _refine_ls_number_reflns 3702 _refine_ls_number_restraints 1 _refine_ls_restrained_S_all 1.034 _refine_ls_R_factor_all 0.0537 _refine_ls_R_factor_gt 0.0444 _refine_ls_shift/su_max 0.000 _refine_ls_shift/su_mean 0.000 _refine_ls_structure_factor_coef Fsqd _refine_ls_weighting_details 'W=1/[\S^2^(FO^2^)+(0.0315P)^2^] WHERE P=(FO^2^+2FC^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_gt 0.0812 _refine_ls_wR_factor_ref 0.0859 _reflns_number_gt 3223 _reflns_number_total 3702 _reflns_threshold_expression 'I > 2\s(I)' _[local]_cod_data_source_file c4cc08751h2.cif _[local]_cod_data_source_block shelx_1 _[local]_cod_cif_authors_sg_H-M 'P 21' _cod_database_code 7116328 loop_ _symmetry_equiv_pos_site_id _symmetry_equiv_pos_as_xyz 1 x,y,z 2 -x,1/2+y,-z 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 S1 0.0469(7) 0.0357(5) 0.0761(8) -0.0060(6) -0.0015(6) 0.0084(5) O1 0.0170(12) 0.0286(12) 0.0205(11) -0.0052(10) 0.0043(9) -0.0015(10) O2 0.0157(13) 0.0353(13) 0.0307(13) -0.0080(11) 0.0031(10) -0.0037(10) N1 0.0124(14) 0.0350(16) 0.0227(14) -0.0064(13) 0.0008(11) -0.0023(12) N2 0.067(3) 0.0328(19) 0.038(2) 0.0051(16) 0.0040(19) -0.0054(18) C1 0.028(2) 0.031(2) 0.0253(18) -0.0018(16) 0.0008(16) -0.0038(16) C2 0.037(2) 0.034(2) 0.033(2) 0.0082(17) -0.0031(18) -0.0127(18) C3 0.040(2) 0.0210(18) 0.043(2) 0.0046(17) -0.0075(19) -0.0052(16) C4 0.034(2) 0.0225(17) 0.037(2) -0.0061(16) -0.0009(18) -0.0009(16) C5 0.0209(18) 0.0225(16) 0.0246(18) -0.0038(14) -0.0038(15) -0.0013(14) C6 0.0207(17) 0.0247(18) 0.0220(16) -0.0055(14) -0.0007(14) -0.0020(14) C7 0.0256(19) 0.0330(18) 0.0302(19) -0.0113(17) 0.0026(15) 0.0039(16) C8 0.027(2) 0.045(2) 0.0254(19) -0.0060(18) 0.0088(16) -0.0032(17) C9 0.033(2) 0.043(2) 0.0258(19) 0.0050(17) 0.0063(17) -0.0076(18) C10 0.0269(19) 0.0272(17) 0.0247(18) 0.0018(16) 0.0028(15) 0.0001(15) C11 0.0205(18) 0.0283(18) 0.0180(16) -0.0011(15) -0.0014(14) -0.0017(14) C12 0.0208(18) 0.0216(16) 0.0203(17) 0.0010(14) 0.0027(14) 0.0008(14) C13 0.0197(17) 0.0235(18) 0.0209(17) -0.0021(14) -0.0003(14) -0.0038(14) C14 0.0206(18) 0.0231(16) 0.0259(17) -0.0017(14) 0.0082(14) -0.0005(14) C15 0.0177(17) 0.0185(16) 0.0258(17) 0.0000(14) -0.0006(14) 0.0005(13) C16 0.0193(17) 0.0322(18) 0.0202(17) -0.0033(15) 0.0023(14) -0.0068(15) C17 0.045(2) 0.038(2) 0.0267(19) -0.0053(18) 0.0063(18) -0.0152(19) C18 0.045(3) 0.028(2) 0.043(2) 0.0062(19) -0.014(2) -0.0030(19) C19 0.0202(19) 0.041(2) 0.0270(19) -0.0094(17) 0.0037(15) -0.0044(16) C20 0.048(2) 0.036(2) 0.0296(19) -0.0077(18) 0.0096(18) -0.0121(19) C21 0.056(3) 0.039(2) 0.027(2) -0.0006(18) 0.0023(19) 0.0137(19) loop_ _atom_site_label _atom_site_type_symbol _atom_site_thermal_displace_type _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_occupancy _atom_site_U_iso_or_equiv S1 S Uani 1.0123(2) 0.19692(6) 0.32734(11) 1.000 0.0541(4) O1 O Uani 0.5883(4) 0.37267(13) 0.13640(17) 1.000 0.0219(7) O2 O Uani 0.9417(4) 0.42094(14) 0.26216(18) 1.000 0.0273(8) N1 N Uani 0.5160(5) 0.40990(17) 0.3066(2) 1.000 0.0236(8) N2 N Uani 0.6957(8) 0.2790(2) 0.4615(3) 1.000 0.0464(14) C1 C Uani 0.4741(7) 0.1799(2) 0.0769(3) 1.000 0.0285(11) C2 C Uani 0.4889(8) 0.0931(2) 0.0953(3) 1.000 0.0356(12) C3 C Uani 0.6387(8) 0.0431(2) 0.0329(3) 1.000 0.0362(11) C4 C Uani 0.7750(8) 0.0767(2) -0.0485(3) 1.000 0.0319(11) C5 C Uani 0.7635(7) 0.16302(19) -0.0652(3) 1.000 0.0235(10) C6 C Uani 0.8858(7) 0.21563(19) -0.1432(3) 1.000 0.0229(10) C7 C Uani 1.0544(7) 0.1959(2) -0.2212(3) 1.000 0.0298(11) C8 C Uani 1.1426(7) 0.2591(3) -0.2851(3) 1.000 0.0320(11) C9 C Uani 1.0649(8) 0.3421(2) -0.2712(3) 1.000 0.0338(11) C10 C Uani 0.8989(7) 0.3626(2) -0.1931(3) 1.000 0.0264(10) C11 C Uani 0.8102(7) 0.2993(2) -0.1292(3) 1.000 0.0228(10) C12 C Uani 0.6359(7) 0.30582(19) -0.0370(3) 1.000 0.0210(10) C13 C Uani 0.6135(7) 0.21403(19) -0.0027(3) 1.000 0.0218(10) C14 C Uani 0.7741(7) 0.3613(2) 0.0572(3) 1.000 0.0227(10) C15 C Uani 0.7011(6) 0.40275(19) 0.2384(3) 1.000 0.0211(10) C16 C Uani 0.5869(7) 0.4266(2) 0.4260(3) 1.000 0.0240(10) C17 C Uani 0.5366(8) 0.3472(2) 0.4910(3) 1.000 0.0365(11) C18 C Uani 0.8274(9) 0.2461(2) 0.4015(4) 1.000 0.0410(14) C19 C Uani 0.4363(7) 0.5036(2) 0.4626(3) 1.000 0.0294(11) C20 C Uani 0.5151(8) 0.5207(2) 0.5884(3) 1.000 0.0375(11) C21 C Uani 0.4990(9) 0.5802(3) 0.3963(3) 1.000 0.0411(14) H1 H Uiso 0.37029 0.21463 0.11822 1.000 0.0339 H1N H Uiso 0.34315 0.40420 0.27784 1.000 0.0283 H2 H Uiso 0.39676 0.06838 0.15038 1.000 0.0426 H3 H Uiso 0.64776 -0.01566 0.04636 1.000 0.0434 H4 H Uiso 0.87361 0.04165 -0.09153 1.000 0.0381 H7 H Uiso 1.10828 0.13947 -0.23031 1.000 0.0357 H8 H Uiso 1.25669 0.24596 -0.33883 1.000 0.0384 H9 H Uiso 1.12640 0.38509 -0.31571 1.000 0.0403 H10 H Uiso 0.84689 0.41921 -0.18358 1.000 0.0317 H12 H Uiso 0.45225 0.32864 -0.06808 1.000 0.0251 H14A H Uiso 0.94414 0.33465 0.09468 1.000 0.0272 H14B H Uiso 0.82018 0.41632 0.02686 1.000 0.0272 H16 H Uiso 0.78620 0.43898 0.44184 1.000 0.0288 H17A H Uiso 0.58288 0.35810 0.57270 1.000 0.0439 H17B H Uiso 0.34152 0.33211 0.47433 1.000 0.0439 H19 H Uiso 0.23621 0.49256 0.44604 1.000 0.0353 H20A H Uiso 0.71308 0.52635 0.60702 1.000 0.0562 H20B H Uiso 0.45438 0.47393 0.63112 1.000 0.0562 H20C H Uiso 0.42835 0.57272 0.60777 1.000 0.0562 H21A H Uiso 0.39968 0.62879 0.41888 1.000 0.0620 H21B H Uiso 0.44312 0.56972 0.31576 1.000 0.0620 H21C H Uiso 0.69480 0.59163 0.41145 1.000 0.0620 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source S S 0.1246 0.1234 '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' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' C C 0.0033 0.0016 '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 C14 O1 C15 115.3(2) yes C15 N1 C16 122.9(3) yes C17 N2 C18 152.0(4) yes C15 N1 H1N 119.00 no C16 N1 H1N 119.00 no C2 C1 C13 118.6(3) no C1 C2 C3 119.9(3) no C2 C3 C4 121.8(3) no C3 C4 C5 118.1(3) no C6 C5 C13 109.0(3) no C4 C5 C13 120.6(3) no C4 C5 C6 130.4(3) no C5 C6 C11 108.7(3) no C7 C6 C11 119.9(3) no C5 C6 C7 131.5(3) no C6 C7 C8 119.4(3) no C7 C8 C9 120.3(3) no C8 C9 C10 120.8(3) no C9 C10 C11 118.9(3) no C6 C11 C12 110.4(3) no C10 C11 C12 128.9(3) no C6 C11 C10 120.7(3) no C13 C12 C14 113.6(3) no C11 C12 C13 102.0(3) no C11 C12 C14 110.1(3) no C5 C13 C12 110.0(3) no C1 C13 C12 129.1(3) no C1 C13 C5 121.0(3) no O1 C14 C12 107.8(3) yes O1 C15 O2 123.1(3) yes O1 C15 N1 111.2(3) yes O2 C15 N1 125.7(3) yes N1 C16 C17 108.8(3) yes C17 C16 C19 112.7(3) no N1 C16 C19 112.2(3) yes N2 C17 C16 111.1(3) yes S1 C18 N2 175.9(4) yes C20 C19 C21 109.7(3) no C16 C19 C20 111.5(3) no C16 C19 C21 109.9(3) no C2 C1 H1 121.00 no C13 C1 H1 121.00 no C1 C2 H2 120.00 no C3 C2 H2 120.00 no C2 C3 H3 119.00 no C4 C3 H3 119.00 no C3 C4 H4 121.00 no C5 C4 H4 121.00 no C6 C7 H7 120.00 no C8 C7 H7 120.00 no C7 C8 H8 120.00 no C9 C8 H8 120.00 no C8 C9 H9 120.00 no C10 C9 H9 120.00 no C9 C10 H10 121.00 no C11 C10 H10 120.00 no C11 C12 H12 110.00 no C13 C12 H12 110.00 no C14 C12 H12 110.00 no O1 C14 H14A 110.00 no O1 C14 H14B 110.00 no C12 C14 H14A 110.00 no C12 C14 H14B 110.00 no H14A C14 H14B 108.00 no N1 C16 H16 108.00 no C17 C16 H16 108.00 no C19 C16 H16 108.00 no N2 C17 H17A 109.00 no N2 C17 H17B 109.00 no C16 C17 H17A 109.00 no C16 C17 H17B 109.00 no H17A C17 H17B 108.00 no C16 C19 H19 109.00 no C20 C19 H19 109.00 no C21 C19 H19 109.00 no C19 C20 H20A 109.00 no C19 C20 H20B 109.00 no C19 C20 H20C 109.00 no H20A C20 H20B 109.00 no H20A C20 H20C 109.00 no H20B C20 H20C 109.00 no C19 C21 H21A 109.00 no C19 C21 H21B 110.00 no C19 C21 H21C 109.00 no H21A C21 H21B 109.00 no H21A C21 H21C 109.00 no H21B C21 H21C 109.00 no loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_publ_flag S1 C18 1.588(4) yes O1 C14 1.443(4) yes O1 C15 1.355(4) yes O2 C15 1.222(4) yes N1 C15 1.334(4) yes N1 C16 1.450(4) yes N2 C17 1.423(5) yes N2 C18 1.174(6) yes N1 H1N 0.8800 no C1 C2 1.401(5) no C1 C13 1.382(5) no C2 C3 1.391(5) no C3 C4 1.386(5) no C4 C5 1.390(4) no C5 C13 1.402(5) no C5 C6 1.462(5) no C6 C11 1.403(4) no C6 C7 1.392(5) no C7 C8 1.381(5) no C8 C9 1.395(6) no C9 C10 1.387(5) no C10 C11 1.383(5) no C11 C12 1.518(5) no C12 C14 1.514(5) no C12 C13 1.528(4) no C16 C17 1.529(5) no C16 C19 1.539(5) no C19 C20 1.528(5) no C19 C21 1.518(6) no C1 H1 0.9500 no C2 H2 0.9500 no C3 H3 0.9500 no C4 H4 0.9500 no C7 H7 0.9500 no C8 H8 0.9500 no C9 H9 0.9500 no C10 H10 0.9500 no C12 H12 1.0000 no C14 H14A 0.9900 no C14 H14B 0.9900 no C16 H16 1.0000 no C17 H17A 0.9900 no C17 H17B 0.9900 no C19 H19 1.0000 no C20 H20A 0.9800 no C20 H20B 0.9800 no C20 H20C 0.9800 no C21 H21A 0.9800 no C21 H21B 0.9800 no C21 H21C 0.9800 no loop_ _geom_contact_atom_site_label_1 _geom_contact_atom_site_label_2 _geom_contact_distance _geom_contact_site_symmetry_2 _geom_contact_publ_flag S1 C20 3.700(4) 2_746 no S1 H17B 3.0900 1_655 no S1 H20A 3.0900 2_746 no S1 H20C 3.1400 2_646 no O1 C1 3.184(4) . no O2 N1 2.830(3) 1_655 no O2 C18 3.347(4) . no O1 H1 2.7400 . no O2 H1N 2.0000 1_655 no O2 H14A 2.4400 . no O2 H14B 2.8000 . no O2 H16 2.4300 . no O2 H19 2.7100 1_655 no N1 O2 2.830(3) 1_455 no N1 N2 2.846(4) . no N1 C18 3.155(5) . no N2 N1 2.846(4) . no N2 C15 3.337(5) . no N1 H21B 2.5800 . no N2 H21A 2.8700 2_646 no C1 O1 3.184(4) . no C7 C13 3.525(5) 1_655 no C9 C17 3.568(5) 1_554 no C13 C7 3.525(5) 1_455 no C15 N2 3.337(5) . no C15 C18 3.176(5) . no C17 C9 3.568(5) 1_556 no C18 O2 3.347(4) . no C18 N1 3.155(5) . no C18 C15 3.176(5) . no C20 S1 3.700(4) 2_756 no C3 H14B 3.0500 2_645 no C8 H12 3.0300 1_655 no C9 H12 2.8700 1_655 no C9 H17A 2.8200 1_554 no C10 H12 2.9700 1_655 no C10 H17A 3.0000 1_554 no C10 H14B 2.8700 . no C14 H3 3.0000 2_655 no C17 H20B 2.7000 . no C18 H20C 3.0400 2_646 no C18 H17B 2.9100 1_655 no C20 H17A 2.6200 . no C21 H8 3.0300 2_755 no H1 O1 2.7400 . no H1N O2 2.0000 1_455 no H1N H19 2.5900 . no H3 C14 3.0000 2_645 no H3 H12 2.5500 2_645 no H3 H14B 2.5900 2_645 no H4 H14B 2.5600 2_745 no H8 C21 3.0300 2_745 no H9 H20B 2.3300 1_654 no H10 H14B 2.5600 . no H12 C8 3.0300 1_455 no H12 C9 2.8700 1_455 no H12 C10 2.9700 1_455 no H12 H3 2.5500 2_655 no H14A O2 2.4400 . no H14B O2 2.8000 . no H14B C10 2.8700 . no H14B H10 2.5600 . no H14B C3 3.0500 2_655 no H14B H3 2.5900 2_655 no H14B H4 2.5600 2_755 no H16 O2 2.4300 . no H16 H19 2.3900 1_655 no H16 H20A 2.5000 . no H16 H21C 2.4900 . no H17A C9 2.8200 1_556 no H17A C10 3.0000 1_556 no H17A C20 2.6200 . no H17A H20B 2.1100 . no H17B S1 3.0900 1_455 no H17B C18 2.9100 1_455 no H19 O2 2.7100 1_455 no H19 H1N 2.5900 . no H19 H16 2.3900 1_455 no H20A H16 2.5000 . no H20A H21C 2.5600 . no H20A S1 3.0900 2_756 no H20B C17 2.7000 . no H20B H9 2.3300 1_456 no H20B H17A 2.1100 . no H20C H21A 2.4300 . no H20C S1 3.1400 2_656 no H20C C18 3.0400 2_656 no H21A H20C 2.4300 . no H21A N2 2.8700 2_656 no H21B N1 2.5800 . no H21C H16 2.4900 . no H21C H20A 2.5600 . no 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 _geom_hbond_publ_flag N1 H1N O2 0.8800 2.0000 2.830(3) 158.00 1_455 yes C16 H16 O2 1.0000 2.4300 2.853(4) 105.00 . yes C21 H21B N1 0.9800 2.5800 2.926(5) 101.00 . yes 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 C14 O1 C15 N1 -178.9(2) no C15 O1 C14 C12 164.3(3) no C14 O1 C15 O2 1.5(4) no C16 N1 C15 O1 169.1(3) no C15 N1 C16 C19 125.9(3) no C16 N1 C15 O2 -11.4(5) no C15 N1 C16 C17 -108.7(3) no C18 N2 C17 C16 -17.8(10) no C2 C1 C13 C5 1.0(5) no C2 C1 C13 C12 -178.6(3) no C13 C1 C2 C3 -0.9(5) no C1 C2 C3 C4 -0.3(6) no C2 C3 C4 C5 1.3(6) no C3 C4 C5 C6 179.7(4) no C3 C4 C5 C13 -1.2(5) no C6 C5 C13 C1 179.4(3) no C4 C5 C6 C7 -2.0(7) no C4 C5 C6 C11 178.9(4) no C4 C5 C13 C12 179.7(3) no C13 C5 C6 C11 -0.3(4) no C4 C5 C13 C1 0.1(5) no C6 C5 C13 C12 -1.0(4) no C13 C5 C6 C7 178.9(4) no C11 C6 C7 C8 -0.8(5) no C5 C6 C11 C10 180.0(3) no C5 C6 C7 C8 -179.9(4) no C7 C6 C11 C10 0.8(5) no C7 C6 C11 C12 -177.8(3) no C5 C6 C11 C12 1.4(4) no C6 C7 C8 C9 0.4(5) no C7 C8 C9 C10 0.2(6) no C8 C9 C10 C11 -0.3(5) no C9 C10 C11 C6 -0.2(5) no C9 C10 C11 C12 178.1(3) no C10 C11 C12 C13 179.7(4) no C6 C11 C12 C14 119.0(3) no C10 C11 C12 C14 -59.5(5) no C6 C11 C12 C13 -1.9(4) no C11 C12 C13 C1 -178.7(4) no C14 C12 C13 C1 62.9(5) no C14 C12 C13 C5 -116.7(3) no C11 C12 C13 C5 1.7(4) no C13 C12 C14 O1 -72.5(3) no C11 C12 C14 O1 174.0(2) no C19 C16 C17 N2 -175.3(3) no N1 C16 C19 C20 -179.5(3) no N1 C16 C17 N2 59.6(4) no C17 C16 C19 C20 57.3(4) no C17 C16 C19 C21 179.0(3) no N1 C16 C19 C21 -57.8(4) no