Supplementary Material (ESI) for Green Chemistry This journal is (c) The Royal Society of Chemistry 2006 data_global _journal_coden_Cambridge 1048 _publ_contact_author_name 'Juliusz Pernak' _publ_contact_author_address ;Poznan University of Technology, Faculty of Chemical Technology, Poznan, Poland ; _publ_contact_author_email juliusz@pernak.com.pl loop_ _publ_author_name 'Juliusz Pernak' 'Andrzej Fojutowski' 'Kazimierz Kita' 'Anna Pernak' 'Robin D. Rogers' 'Marcin Smiglak' 'Jadwiga Zabielska-Matejuk' _publ_requested_journal 'Green Chemistry' _publ_section_title ; Long alkyl chain quaternary ammonium-based ionic liquids and potential applications ; data_s1 _database_code_depnum_ccdc_archive 'CCDC 602689' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common 'benzethonium nitrate' _chemical_melting_point 94 _chemical_formula_moiety ? _chemical_formula_sum 'C27 H42 N2 O5' _chemical_formula_weight 474.63 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 Triclinic _symmetry_space_group_name_H-M P-1 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 7.936(3) _cell_length_b 10.048(4) _cell_length_c 17.864(7) _cell_angle_alpha 91.753(8) _cell_angle_beta 102.116(7) _cell_angle_gamma 106.858(7) _cell_volume 1326.5(10) _cell_formula_units_Z 2 _cell_measurement_temperature 173(2) _cell_measurement_reflns_used 1862 _cell_measurement_theta_min 2.33 _cell_measurement_theta_max 23.19 _exptl_crystal_description Plate _exptl_crystal_colour Colorless _exptl_crystal_size_max 0.56 _exptl_crystal_size_mid 0.12 _exptl_crystal_size_min 0.03 _exptl_crystal_density_meas 0 _exptl_crystal_density_diffrn 1.188 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 516 _exptl_absorpt_coefficient_mu 0.081 _exptl_absorpt_correction_type Sphere _exptl_absorpt_correction_T_min ? _exptl_absorpt_correction_T_max ? _exptl_absorpt_process_details SADABS _exptl_special_details ; ? ; _diffrn_ambient_temperature 173(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 5237 _diffrn_reflns_av_R_equivalents 0.0000 _diffrn_reflns_av_sigmaI/netI 0.1119 _diffrn_reflns_limit_h_min -9 _diffrn_reflns_limit_h_max 9 _diffrn_reflns_limit_k_min -12 _diffrn_reflns_limit_k_max 12 _diffrn_reflns_limit_l_min -11 _diffrn_reflns_limit_l_max 22 _diffrn_reflns_theta_min 2.13 _diffrn_reflns_theta_max 26.41 _reflns_number_total 5238 _reflns_number_gt 3333 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'Bruker SMART' _computing_data_reduction 'Bruker SAINT' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _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^)+(0.1870P)^2^+2.0752P] 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 0.25(3) _refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^ _refine_ls_number_reflns 5238 _refine_ls_number_parameters 317 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.1503 _refine_ls_R_factor_gt 0.1123 _refine_ls_wR_factor_ref 0.3388 _refine_ls_wR_factor_gt 0.3193 _refine_ls_goodness_of_fit_ref 1.046 _refine_ls_restrained_S_all 1.046 _refine_ls_shift/su_max 0.001 _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 O1 O 0.9291(5) 0.6648(4) 0.0322(2) 0.0310(9) Uani 1 1 d . . . O2 O 0.5904(5) 0.5996(4) 0.0925(2) 0.0328(10) Uani 1 1 d . . . O3 O 0.4429(6) 0.0623(5) 0.0871(3) 0.0472(12) Uani 1 1 d . . . O4 O 0.1829(6) 0.0440(5) 0.1115(3) 0.0495(12) Uani 1 1 d . . . O5 O 0.4222(7) 0.1869(6) 0.1833(3) 0.0634(15) Uani 1 1 d . . . N1 N 1.0792(6) 0.7137(4) -0.1205(2) 0.0240(10) Uani 1 1 d . . . N2 N 0.3494(6) 0.0976(4) 0.1269(3) 0.0295(11) Uani 1 1 d . . . C1 C 1.1361(7) 0.8053(5) -0.0439(3) 0.0269(12) Uani 1 1 d . . . H1A H 1.2650 0.8604 -0.0364 0.032 Uiso 1 1 calc R . . H1B H 1.0651 0.8722 -0.0476 0.032 Uiso 1 1 calc R . . C2 C 1.1129(8) 0.7282(6) 0.0273(3) 0.0320(13) Uani 1 1 d . . . H2A H 1.1732 0.6544 0.0283 0.038 Uiso 1 1 calc R . . H2B H 1.1760 0.7949 0.0735 0.038 Uiso 1 1 calc R . . C3 C 0.8417(7) 0.7613(6) 0.0504(3) 0.0291(12) Uani 1 1 d . . . H3A H 0.8668 0.8414 0.0191 0.035 Uiso 1 1 calc R . . H3B H 0.8869 0.7973 0.1054 0.035 Uiso 1 1 calc R . . C4 C 0.6402(8) 0.6873(6) 0.0336(3) 0.0322(13) Uani 1 1 d . . . H4A H 0.573(7) 0.754(5) 0.031(3) 0.010(11) Uiso 1 1 d . . . H4B H 0.599(7) 0.613(5) -0.016(3) 0.015(12) Uiso 1 1 d . . . C5 C 0.5715(7) 0.6610(5) 0.1591(3) 0.0271(12) Uani 1 1 d . . . C6 C 0.5498(7) 0.5757(6) 0.2179(3) 0.0309(13) Uani 1 1 d . . . H6A H 0.5511 0.4819 0.2112 0.037 Uiso 1 1 calc R . . C7 C 0.5258(7) 0.6275(6) 0.2872(3) 0.0326(13) Uani 1 1 d . . . H7A H 0.5122 0.5679 0.3273 0.039 Uiso 1 1 calc R . . C8 C 0.5211(7) 0.7636(6) 0.2993(3) 0.0267(12) Uani 1 1 d . . . C9 C 0.5437(7) 0.8481(6) 0.2385(3) 0.0318(13) Uani 1 1 d . . . H9A H 0.5425 0.9420 0.2450 0.038 Uiso 1 1 calc R . . C10 C 0.5679(7) 0.7983(5) 0.1690(3) 0.0284(12) Uani 1 1 d . . . H10A H 0.5818 0.8573 0.1287 0.034 Uiso 1 1 calc R . . C11 C 0.4988(8) 0.8272(6) 0.3745(3) 0.0347(13) Uani 1 1 d . . . C12 C 0.4731(10) 0.7182(8) 0.4335(4) 0.0470(17) Uani 1 1 d . . . H12A H 0.5735 0.6780 0.4413 0.070 Uiso 1 1 calc R . . H12B H 0.3588 0.6439 0.4141 0.070 Uiso 1 1 calc R . . H12C H 0.4709 0.7635 0.4824 0.070 Uiso 1 1 calc R . . C13 C 0.6738(10) 0.9459(8) 0.4099(4) 0.056(2) Uani 1 1 d . . . H13A H 0.7763 0.9081 0.4202 0.083 Uiso 1 1 calc R . . H13B H 0.6623 0.9876 0.4582 0.083 Uiso 1 1 calc R . . H13C H 0.6940 1.0175 0.3740 0.083 Uiso 1 1 calc R . . C14 C 0.3439(8) 0.8934(6) 0.3600(3) 0.0326(13) Uani 1 1 d . . . H14A H 0.3689 0.9601 0.3211 0.039 Uiso 1 1 calc R . . H14B H 0.3562 0.9500 0.4083 0.039 Uiso 1 1 calc R . . C15 C 0.1409(8) 0.8067(6) 0.3336(3) 0.0332(13) Uani 1 1 d . . . C16 C 0.1028(8) 0.6862(7) 0.2710(4) 0.0413(15) Uani 1 1 d . . . H16A H -0.0270 0.6360 0.2574 0.062 Uiso 1 1 calc R . . H16B H 0.1701 0.6218 0.2904 0.062 Uiso 1 1 calc R . . H16C H 0.1411 0.7241 0.2253 0.062 Uiso 1 1 calc R . . C17 C 0.0398(10) 0.9082(7) 0.3017(4) 0.0483(17) Uani 1 1 d . . . H17A H -0.0895 0.8579 0.2842 0.072 Uiso 1 1 calc R . . H17B H 0.0866 0.9496 0.2584 0.072 Uiso 1 1 calc R . . H17C H 0.0572 0.9823 0.3422 0.072 Uiso 1 1 calc R . . C18 C 0.0599(10) 0.7449(7) 0.4014(4) 0.0456(16) Uani 1 1 d . . . H18A H -0.0675 0.6908 0.3819 0.068 Uiso 1 1 calc R . . H18B H 0.0690 0.8211 0.4391 0.068 Uiso 1 1 calc R . . H18C H 0.1270 0.6839 0.4260 0.068 Uiso 1 1 calc R . . C19 C 1.1999(8) 0.6249(6) -0.1224(3) 0.0314(13) Uani 1 1 d . . . H19A H 1.1851 0.5589 -0.0832 0.047 Uiso 1 1 calc R . . H19B H 1.3260 0.6843 -0.1119 0.047 Uiso 1 1 calc R . . H19C H 1.1680 0.5731 -0.1733 0.047 Uiso 1 1 calc R . . C20 C 0.8854(7) 0.6233(5) -0.1363(3) 0.0310(13) Uani 1 1 d . . . H20A H 0.8706 0.5575 -0.0971 0.047 Uiso 1 1 calc R . . H20B H 0.8527 0.5712 -0.1872 0.047 Uiso 1 1 calc R . . H20C H 0.8067 0.6821 -0.1350 0.047 Uiso 1 1 calc R . . C21 C 1.1022(8) 0.8172(5) -0.1822(3) 0.0315(13) Uani 1 1 d . . . H21A H 1.0320 0.8823 -0.1765 0.038 Uiso 1 1 calc R . . H21B H 1.2313 0.8732 -0.1724 0.038 Uiso 1 1 calc R . . C22 C 1.0433(9) 0.7509(6) -0.2642(3) 0.0350(14) Uani 1 1 d . . . C23 C 0.8656(10) 0.7297(6) -0.3040(4) 0.0446(16) Uani 1 1 d . . . H23A H 0.7824 0.7530 -0.2788 0.054 Uiso 1 1 calc R . . C24 C 0.8093(11) 0.6742(8) -0.3811(4) 0.0553(19) Uani 1 1 d . . . H24A H 0.6877 0.6586 -0.4083 0.066 Uiso 1 1 calc R . . C25 C 0.9347(11) 0.6416(8) -0.4179(4) 0.0547(19) Uani 1 1 d . . . H25A H 0.8979 0.6038 -0.4702 0.066 Uiso 1 1 calc R . . C26 C 1.1057(12) 0.6638(7) -0.3792(4) 0.0530(19) Uani 1 1 d . . . H26A H 1.1900 0.6433 -0.4049 0.064 Uiso 1 1 calc R . . C27 C 1.1626(10) 0.7167(7) -0.3019(4) 0.0448(16) Uani 1 1 d . . . H27A H 1.2838 0.7293 -0.2751 0.054 Uiso 1 1 calc R . . 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 0.031(2) 0.0290(18) 0.037(2) 0.0073(16) 0.0152(17) 0.0102(16) O2 0.035(2) 0.0313(19) 0.034(2) -0.0006(17) 0.0143(17) 0.0086(17) O3 0.039(3) 0.049(3) 0.062(3) 0.008(2) 0.019(2) 0.020(2) O4 0.025(2) 0.045(2) 0.075(3) 0.002(2) 0.007(2) 0.0102(19) O5 0.047(3) 0.063(3) 0.069(3) -0.021(3) 0.003(3) 0.010(2) N1 0.020(2) 0.023(2) 0.030(2) 0.0067(18) 0.0079(19) 0.0061(16) N2 0.024(2) 0.026(2) 0.042(3) 0.010(2) 0.009(2) 0.0102(18) C1 0.022(3) 0.023(2) 0.035(3) 0.001(2) 0.007(2) 0.005(2) C2 0.032(3) 0.035(3) 0.036(3) 0.010(2) 0.016(3) 0.016(2) C3 0.028(3) 0.032(3) 0.028(3) 0.001(2) 0.013(2) 0.006(2) C4 0.036(3) 0.032(3) 0.029(3) 0.001(2) 0.009(3) 0.009(2) C5 0.020(3) 0.031(3) 0.028(3) 0.000(2) 0.007(2) 0.004(2) C6 0.028(3) 0.028(3) 0.040(3) 0.004(2) 0.010(2) 0.010(2) C7 0.026(3) 0.044(3) 0.034(3) 0.010(3) 0.012(2) 0.014(2) C8 0.018(3) 0.037(3) 0.026(3) 0.005(2) 0.007(2) 0.009(2) C9 0.030(3) 0.033(3) 0.033(3) -0.003(2) 0.007(2) 0.011(2) C10 0.026(3) 0.028(3) 0.031(3) 0.002(2) 0.008(2) 0.007(2) C11 0.029(3) 0.043(3) 0.032(3) -0.003(3) 0.006(2) 0.012(3) C12 0.050(4) 0.071(4) 0.032(3) 0.013(3) 0.016(3) 0.031(4) C13 0.041(4) 0.070(5) 0.043(4) -0.018(3) 0.009(3) 0.001(3) C14 0.035(3) 0.032(3) 0.030(3) -0.004(2) 0.009(2) 0.008(2) C15 0.034(3) 0.037(3) 0.031(3) 0.005(2) 0.009(2) 0.014(2) C16 0.028(3) 0.048(3) 0.043(4) -0.012(3) 0.006(3) 0.006(3) C17 0.053(4) 0.053(4) 0.049(4) 0.015(3) 0.012(3) 0.031(3) C18 0.044(4) 0.048(4) 0.049(4) 0.006(3) 0.023(3) 0.011(3) C19 0.036(3) 0.030(3) 0.037(3) 0.008(2) 0.013(3) 0.020(2) C20 0.026(3) 0.027(3) 0.035(3) 0.000(2) 0.004(2) 0.003(2) C21 0.042(3) 0.025(3) 0.028(3) 0.010(2) 0.007(2) 0.011(2) C22 0.045(4) 0.026(3) 0.031(3) 0.009(2) 0.005(3) 0.009(2) C23 0.056(4) 0.044(3) 0.030(3) 0.014(3) 0.002(3) 0.014(3) C24 0.057(5) 0.057(4) 0.038(4) 0.014(3) -0.005(3) 0.007(4) C25 0.070(5) 0.056(4) 0.027(3) 0.006(3) 0.008(3) 0.004(4) C26 0.071(5) 0.048(4) 0.039(4) 0.005(3) 0.023(4) 0.009(4) C27 0.054(4) 0.044(3) 0.035(3) 0.009(3) 0.015(3) 0.009(3) _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 O1 C3 1.412(6) . ? O1 C2 1.435(7) . ? O2 C5 1.379(6) . ? O2 C4 1.438(7) . ? O3 N2 1.241(6) . ? O4 N2 1.240(6) . ? O5 N2 1.247(7) . ? N1 C19 1.491(6) . ? N1 C20 1.504(7) . ? N1 C1 1.532(7) . ? N1 C21 1.541(7) . ? C1 C2 1.525(8) . ? C3 C4 1.515(8) . ? C5 C6 1.383(8) . ? C5 C10 1.394(7) . ? C6 C7 1.400(8) . ? C7 C8 1.390(8) . ? C8 C9 1.408(8) . ? C8 C11 1.534(8) . ? C9 C10 1.396(8) . ? C11 C14 1.540(8) . ? C11 C13 1.541(9) . ? C11 C12 1.544(9) . ? C14 C15 1.555(8) . ? C15 C17 1.525(8) . ? C15 C16 1.540(8) . ? C15 C18 1.551(9) . ? C21 C22 1.511(8) . ? C22 C27 1.381(9) . ? C22 C23 1.391(9) . ? C23 C24 1.398(10) . ? C24 C25 1.408(11) . ? C25 C26 1.338(11) . ? C26 C27 1.396(9) . ? 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 C3 O1 C2 113.9(4) . . ? C5 O2 C4 118.4(4) . . ? C19 N1 C20 109.8(4) . . ? C19 N1 C1 110.7(4) . . ? C20 N1 C1 112.3(4) . . ? C19 N1 C21 109.4(4) . . ? C20 N1 C21 109.4(4) . . ? C1 N1 C21 105.1(4) . . ? O4 N2 O3 120.6(5) . . ? O4 N2 O5 119.1(5) . . ? O3 N2 O5 120.3(5) . . ? C2 C1 N1 116.0(4) . . ? O1 C2 C1 115.1(5) . . ? O1 C3 C4 108.3(4) . . ? O2 C4 C3 112.2(5) . . ? O2 C5 C6 115.7(5) . . ? O2 C5 C10 124.5(5) . . ? C6 C5 C10 119.7(5) . . ? C5 C6 C7 120.0(5) . . ? C8 C7 C6 122.0(5) . . ? C7 C8 C9 116.7(5) . . ? C7 C8 C11 124.4(5) . . ? C9 C8 C11 118.8(5) . . ? C10 C9 C8 122.1(5) . . ? C5 C10 C9 119.4(5) . . ? C8 C11 C14 111.7(5) . . ? C8 C11 C13 108.3(5) . . ? C14 C11 C13 106.8(5) . . ? C8 C11 C12 111.1(5) . . ? C14 C11 C12 111.5(5) . . ? C13 C11 C12 107.3(5) . . ? C11 C14 C15 123.3(5) . . ? C17 C15 C16 108.8(5) . . ? C17 C15 C18 106.7(5) . . ? C16 C15 C18 108.0(5) . . ? C17 C15 C14 106.5(5) . . ? C16 C15 C14 114.0(5) . . ? C18 C15 C14 112.5(5) . . ? C22 C21 N1 115.0(4) . . ? C27 C22 C23 119.1(6) . . ? C27 C22 C21 122.0(6) . . ? C23 C22 C21 118.8(6) . . ? C22 C23 C24 120.1(7) . . ? C23 C24 C25 119.3(7) . . ? C26 C25 C24 120.0(7) . . ? C25 C26 C27 121.2(7) . . ? C22 C27 C26 120.2(7) . . ? 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 C19 N1 C1 C2 -66.3(6) . . . . ? C20 N1 C1 C2 56.8(6) . . . . ? C21 N1 C1 C2 175.7(4) . . . . ? C3 O1 C2 C1 -73.1(6) . . . . ? N1 C1 C2 O1 -69.5(6) . . . . ? C2 O1 C3 C4 165.5(4) . . . . ? C5 O2 C4 C3 80.7(6) . . . . ? O1 C3 C4 O2 77.5(5) . . . . ? C4 O2 C5 C6 -170.9(5) . . . . ? C4 O2 C5 C10 11.1(8) . . . . ? O2 C5 C6 C7 -178.7(5) . . . . ? C10 C5 C6 C7 -0.5(8) . . . . ? C5 C6 C7 C8 0.6(8) . . . . ? C6 C7 C8 C9 -0.7(8) . . . . ? C6 C7 C8 C11 -178.8(5) . . . . ? C7 C8 C9 C10 0.6(8) . . . . ? C11 C8 C9 C10 178.9(5) . . . . ? O2 C5 C10 C9 178.4(5) . . . . ? C6 C5 C10 C9 0.5(8) . . . . ? C8 C9 C10 C5 -0.5(8) . . . . ? C7 C8 C11 C14 -127.8(6) . . . . ? C9 C8 C11 C14 54.0(7) . . . . ? C7 C8 C11 C13 114.9(6) . . . . ? C9 C8 C11 C13 -63.3(7) . . . . ? C7 C8 C11 C12 -2.7(8) . . . . ? C9 C8 C11 C12 179.2(5) . . . . ? C8 C11 C14 C15 69.4(7) . . . . ? C13 C11 C14 C15 -172.5(5) . . . . ? C12 C11 C14 C15 -55.6(7) . . . . ? C11 C14 C15 C17 -162.4(5) . . . . ? C11 C14 C15 C16 -42.4(7) . . . . ? C11 C14 C15 C18 81.1(7) . . . . ? C19 N1 C21 C22 64.5(6) . . . . ? C20 N1 C21 C22 -55.8(6) . . . . ? C1 N1 C21 C22 -176.6(5) . . . . ? N1 C21 C22 C27 -92.4(7) . . . . ? N1 C21 C22 C23 90.7(6) . . . . ? C27 C22 C23 C24 0.2(9) . . . . ? C21 C22 C23 C24 177.2(6) . . . . ? C22 C23 C24 C25 -0.7(10) . . . . ? C23 C24 C25 C26 0.0(11) . . . . ? C24 C25 C26 C27 1.3(11) . . . . ? C23 C22 C27 C26 1.0(9) . . . . ? C21 C22 C27 C26 -175.9(5) . . . . ? C25 C26 C27 C22 -1.8(10) . . . . ? 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 C1 H1B O4 0.99 2.44 3.349(7) 152.0 2_665 C27 H27A O5 0.95 2.45 3.373(9) 163.3 2_765 C21 H21A O4 0.99 2.51 3.403(7) 149.5 2_665 C20 H20C O5 0.98 2.56 3.499(8) 159.5 2_665 C1 H1A O3 0.99 2.58 3.478(7) 150.1 2_765 C21 H21B O3 0.99 2.60 3.485(8) 149.4 2_765 C19 H19B O3 0.98 2.63 3.503(7) 148.3 2_765 C19 H19B O5 0.98 2.64 3.458(8) 141.2 2_765 C3 H3A O4 0.99 2.64 3.544(8) 151.9 2_665 C4 H4B O2 1.07(5) 2.41(5) 3.398(7) 154(4) 2_665 C2 H2B O4 0.99 2.56 3.313(7) 133.3 1_665 _diffrn_measured_fraction_theta_max 0.963 _diffrn_reflns_theta_full 25.30 _diffrn_measured_fraction_theta_full 0.977 _refine_diff_density_max 0.532 _refine_diff_density_min -0.469 _refine_diff_density_rms 0.136