data_150708_s2_lh_m _audit_creation_date 2015-09-15 _audit_creation_method ; Olex2 1.2-beta (compiled 2015.09.11 svn.r3215 for OlexSys, GUI svn.r5093) ; _publ_contact_author_address ? _publ_contact_author_email ? _publ_contact_author_name '' _publ_contact_author_phone ? _publ_section_references ; Dolomanov, O.V., Bourhis, L.J., Gildea, R.J, Howard, J.A.K. & Puschmann, H. (2009), J. Appl. Cryst. 42, 339-341. Palatinus, L. & Chapuis, G. (2007). J. Appl. Cryst., 40, 786-790; Palatinus, L. & van der Lee, A. (2008). J. Appl. Cryst. 41, 975-984; Palatinus, L., Prathapa, S. J. & van Smaalen, S. (2012). J. Appl. Cryst. 45, 575-580. Sheldrick, G.M. (2015). Acta Cryst. C71, 3-8. ; _chemical_name_common ? _chemical_name_systematic ; ? ; _chemical_formula_moiety 'C20 H25 N3 O3' _chemical_formula_sum 'C20 H25 N3 O3' _chemical_formula_weight 355.43 _chemical_melting_point ? 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' _space_group_crystal_system 'triclinic' _space_group_IT_number 2 _space_group_name_H-M_alt 'P -1' _space_group_name_Hall '-P 1' loop_ _space_group_symop_id _space_group_symop_operation_xyz 1 'x, y, z' 2 '-x, -y, -z' _cell_length_a 6.0164(5) _cell_length_b 6.6483(8) _cell_length_c 24.700(3) _cell_angle_alpha 83.957(10) _cell_angle_beta 89.451(9) _cell_angle_gamma 69.222(10) _cell_volume 918.17(18) _cell_formula_units_Z 2 _cell_measurement_reflns_used 1647 _cell_measurement_temperature 293(2) _cell_measurement_theta_max 27.7590 _cell_measurement_theta_min 3.3090 _exptl_absorpt_coefficient_mu 0.088 _exptl_absorpt_correction_T_max 1.00000 _exptl_absorpt_correction_T_min 0.92553 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details ; CrysAlisPro, Agilent Technologies, Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET) (compiled Aug 13 2014,18:06:01) Empirical absorption correction using spherical harmonics, implemented in SCALE3 ABSPACK scaling algorithm. ; _exptl_crystal_colour ? _exptl_crystal_density_diffrn 1.286 _exptl_crystal_density_meas ? _exptl_crystal_density_method 'not measured' _exptl_crystal_description '' _exptl_crystal_F_000 380 _exptl_crystal_size_max 0.3 _exptl_crystal_size_mid 0.2 _exptl_crystal_size_min 0.2 _exptl_special_details ; ? ; _diffrn_reflns_av_R_equivalents 0.0343 _diffrn_reflns_av_unetI/netI 0.0723 _diffrn_reflns_limit_h_max 7 _diffrn_reflns_limit_h_min -7 _diffrn_reflns_limit_k_max 8 _diffrn_reflns_limit_k_min -5 _diffrn_reflns_limit_l_max 30 _diffrn_reflns_limit_l_min -22 _diffrn_reflns_number 6996 _diffrn_reflns_theta_full 26.00 _diffrn_reflns_theta_max 26.37 _diffrn_reflns_theta_min 3.30 _diffrn_ambient_temperature 293.15 _diffrn_detector 'CCD plate' _diffrn_detector_area_resol_mean 16.0874 _diffrn_detector_type Eos _diffrn_measured_fraction_theta_full 0.991 _diffrn_measured_fraction_theta_max 0.991 _diffrn_measurement_details ; #__ type_ start__ end____ width___ exp.time_ 1 omega 25.00 54.00 1.0000 37.5000 omega____ theta____ kappa____ phi______ frames - -14.9669 38.0000 -150.0000 29 #__ type_ start__ end____ width___ exp.time_ 2 omega -14.00 24.00 1.0000 37.5000 omega____ theta____ kappa____ phi______ frames - -14.9669 -99.0000 -30.0000 38 #__ type_ start__ end____ width___ exp.time_ 3 omega -12.00 14.00 1.0000 37.5000 omega____ theta____ kappa____ phi______ frames - -14.9669 -99.0000 60.0000 26 #__ type_ start__ end____ width___ exp.time_ 4 omega -81.00 -3.00 1.0000 37.5000 omega____ theta____ kappa____ phi______ frames - -14.9669 -38.0000 30.0000 78 #__ type_ start__ end____ width___ exp.time_ 5 omega -9.00 82.00 1.0000 37.5000 omega____ theta____ kappa____ phi______ frames - 16.6856 77.0000 -60.0000 91 #__ type_ start__ end____ width___ exp.time_ 6 omega -50.00 43.00 1.0000 37.5000 omega____ theta____ kappa____ phi______ frames - 16.6856 -77.0000 -180.0000 93 ; _diffrn_measurement_device 'four-circle diffractometer' _diffrn_measurement_device_type 'Xcalibur, Eos' _diffrn_measurement_method '\w scans' _diffrn_orient_matrix_UB_11 0.0294526000 _diffrn_orient_matrix_UB_12 -0.0403361000 _diffrn_orient_matrix_UB_13 -0.0256039000 _diffrn_orient_matrix_UB_21 0.1140393000 _diffrn_orient_matrix_UB_22 0.0077208000 _diffrn_orient_matrix_UB_23 0.0023465000 _diffrn_orient_matrix_UB_31 0.0451869000 _diffrn_orient_matrix_UB_32 -0.1071962000 _diffrn_orient_matrix_UB_33 0.0131746000 _diffrn_radiation_monochromator graphite _diffrn_radiation_probe x-ray _diffrn_radiation_type MoK\a _diffrn_radiation_wavelength 0.71073 _diffrn_source 'Enhance (Mo) X-ray Source' _diffrn_standards_decay_% ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_number ? _reflns_number_gt 2240 _reflns_number_total 3732 _reflns_odcompleteness_completeness 99.76 _reflns_odcompleteness_iscentric 1 _reflns_odcompleteness_theta 26.32 _reflns_threshold_expression >2sigma(I) _computing_cell_refinement ; CrysAlisPro, Agilent Technologies, Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET) (compiled Aug 13 2014,18:06:01) ; _computing_data_collection ; CrysAlisPro, Agilent Technologies, Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET) (compiled Aug 13 2014,18:06:01) ; _computing_data_reduction ; CrysAlisPro, Agilent Technologies, Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET) (compiled Aug 13 2014,18:06:01) ; _computing_molecular_graphics 'Olex2 (Dolomanov et al., 2009)' _computing_publication_material 'Olex2 (Dolomanov et al., 2009)' _computing_structure_refinement 'ShelXL (Sheldrick, 2015)' _computing_structure_solution ; Superflip (Palatinus & Chapuis, 2007;Palatinus & van der Lee, 2008; Palatinus et al., 2012) ; _refine_diff_density_max 0.258 _refine_diff_density_min -0.239 _refine_diff_density_rms 0.056 _refine_ls_extinction_coef ? _refine_ls_extinction_method none _refine_ls_goodness_of_fit_ref 1.078 _refine_ls_hydrogen_treatment constr _refine_ls_matrix_type full _refine_ls_number_parameters 235 _refine_ls_number_reflns 3732 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.1462 _refine_ls_R_factor_gt 0.0947 _refine_ls_restrained_S_all 1.078 _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^)+(0.0331P)^2^+1.4927P] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_gt 0.1745 _refine_ls_wR_factor_ref 0.2002 _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. ; _olex2_refinement_description ; 1. Fixed Uiso At 1.2 times of: All C(H) groups, All C(H,H) groups 2.a Secondary CH2 refined with riding coordinates: C1(H1a,H1b), C2(H2a,H2b), C3(H3a,H3b), C5(H5a,H5b), C12(H12a,H12b), C13(H13a, H13b), C17(H17a,H17b), C18(H18a,H18b), C19(H19a,H19b), C20(H20a,H20b) 2.b Aromatic/amide H refined with riding coordinates: C7(H7), C8(H8), C10(H10), C11(H11), C14(H14) ; _atom_sites_solution_hydrogens geom _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap 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_calc_flag _atom_site_disorder_assembly _atom_site_disorder_group _atom_site_refinement_flags_posn O1 O 0.1476(5) 0.9078(5) 0.42112(13) 0.0566(9) Uani 1 d . . . O2 O 1.0302(5) 0.5503(5) 0.20639(12) 0.0516(8) Uani 1 d . . . O3 O 1.4014(8) 0.2799(8) 0.02918(17) 0.1024(15) Uani 1 d . . . N1 N 0.4228(5) 1.0438(5) 0.38793(12) 0.0370(7) Uani 1 d . . . N2 N 0.7453(6) 0.4232(5) 0.23805(13) 0.0406(8) Uani 1 d . . . N3 N 1.1738(6) 0.2605(6) 0.12949(14) 0.0496(9) Uani 1 d . . . C1 C 0.4423(9) 1.3768(8) 0.4194(2) 0.0683(15) Uani 1 d . . . H1A H 0.5602 1.4347 0.4302 0.082 Uiso 1 calc . . R H1B H 0.3324 1.4849 0.3934 0.082 Uiso 1 calc . . R C2 C 0.3106(9) 1.3416(8) 0.4677(2) 0.0640(14) Uani 1 d . . . H2A H 0.2166 1.4806 0.4795 0.077 Uiso 1 calc . . R H2B H 0.4232 1.2608 0.4970 0.077 Uiso 1 calc . . R C3 C 0.1500(8) 1.2214(7) 0.45732(18) 0.0518(11) Uani 1 d . . . H3A H 0.0015 1.3253 0.4415 0.062 Uiso 1 calc . . R H3B H 0.1145 1.1594 0.4922 0.062 Uiso 1 calc . . R C4 C 0.2396(7) 1.0428(6) 0.42087(16) 0.0398(9) Uani 1 d . . . C5 C 0.5629(8) 1.1816(7) 0.39237(19) 0.0545(12) Uani 1 d . . . H5A H 0.6039 1.2253 0.3561 0.065 Uiso 1 calc . . R H5B H 0.7100 1.0973 0.4124 0.065 Uiso 1 calc . . R C6 C 0.5052(6) 0.8827(6) 0.35075(15) 0.0350(8) Uani 1 d . . . C7 C 0.3488(7) 0.8631(6) 0.31266(16) 0.0421(9) Uani 1 d . . . H7 H 0.1897 0.9527 0.3119 0.051 Uiso 1 calc . . R C8 C 0.4264(7) 0.7128(6) 0.27599(16) 0.0417(9) Uani 1 d . . . H8 H 0.3192 0.6995 0.2510 0.050 Uiso 1 calc . . R C9 C 0.6646(7) 0.5806(6) 0.27612(15) 0.0365(9) Uani 1 d . . . C10 C 0.8205(7) 0.5999(6) 0.31412(15) 0.0385(9) Uani 1 d . . . H10 H 0.9797 0.5105 0.3150 0.046 Uiso 1 calc . . R C11 C 0.7407(6) 0.7521(6) 0.35100(15) 0.0375(9) Uani 1 d . . . H11 H 0.8474 0.7658 0.3761 0.045 Uiso 1 calc . . R C12 C 0.5967(7) 0.2962(6) 0.22753(17) 0.0460(10) Uani 1 d . . . H12A H 0.4949 0.3635 0.1955 0.055 Uiso 1 calc . . R H12B H 0.4963 0.2922 0.2583 0.055 Uiso 1 calc . . R C13 C 0.7535(8) 0.0701(6) 0.21872(19) 0.0543(12) Uani 1 d . . . H13A H 0.8342 -0.0056 0.2527 0.065 Uiso 1 calc . . R H13B H 0.6572 -0.0077 0.2066 0.065 Uiso 1 calc . . R C14 C 0.9306(8) 0.0761(7) 0.17748(18) 0.0500(11) Uani 1 d . . . H14 H 0.9937 -0.0407 0.1573 0.060 Uiso 1 calc . . R C15 C 1.0032(7) 0.2441(6) 0.16825(16) 0.0422(10) Uani 1 d . . . C16 C 0.9267(7) 0.4209(6) 0.20551(16) 0.0383(9) Uani 1 d . . . C17 C 1.2881(9) 0.0674(8) 0.1025(2) 0.0680(14) Uani 1 d . . . H17A H 1.1722 0.0421 0.0797 0.082 Uiso 1 calc . . R H17B H 1.3528 -0.0572 0.1294 0.082 Uiso 1 calc . . R C18 C 1.4842(10) 0.0964(12) 0.0681(3) 0.094(2) Uani 1 d . . . H18A H 1.6049 0.1109 0.0916 0.112 Uiso 1 calc . . R H18B H 1.5576 -0.0315 0.0495 0.112 Uiso 1 calc . . R C19 C 1.2965(12) 0.4701(11) 0.0564(2) 0.099(2) Uani 1 d . . . H19A H 1.2388 0.5963 0.0297 0.119 Uiso 1 calc . . R H19B H 1.4155 0.4880 0.0797 0.119 Uiso 1 calc . . R C20 C 1.0940(10) 0.4516(8) 0.0901(2) 0.0706(15) Uani 1 d . . . H20A H 1.0270 0.5795 0.1090 0.085 Uiso 1 calc . . R H20B H 0.9704 0.4436 0.0664 0.085 Uiso 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 0.0593(19) 0.0566(18) 0.070(2) -0.0283(16) 0.0271(16) -0.0351(16) O2 0.0547(18) 0.0582(18) 0.0592(19) -0.0308(15) 0.0202(15) -0.0350(15) O3 0.131(4) 0.138(4) 0.056(3) -0.041(3) 0.046(3) -0.062(3) N1 0.0422(18) 0.0361(17) 0.0383(18) -0.0127(14) 0.0087(14) -0.0185(14) N2 0.0434(19) 0.0433(18) 0.0417(19) -0.0166(15) 0.0083(15) -0.0203(15) N3 0.055(2) 0.057(2) 0.041(2) -0.0230(17) 0.0130(16) -0.0207(18) C1 0.071(3) 0.060(3) 0.092(4) -0.033(3) 0.024(3) -0.039(3) C2 0.078(3) 0.065(3) 0.061(3) -0.039(3) 0.021(3) -0.032(3) C3 0.057(3) 0.048(2) 0.055(3) -0.027(2) 0.019(2) -0.019(2) C4 0.040(2) 0.041(2) 0.042(2) -0.0143(18) 0.0084(17) -0.0149(18) C5 0.067(3) 0.058(3) 0.058(3) -0.028(2) 0.019(2) -0.041(2) C6 0.039(2) 0.039(2) 0.031(2) -0.0103(16) 0.0070(15) -0.0173(17) C7 0.034(2) 0.045(2) 0.047(2) -0.0126(19) 0.0030(17) -0.0121(18) C8 0.037(2) 0.053(2) 0.040(2) -0.0156(19) 0.0023(17) -0.0202(19) C9 0.042(2) 0.041(2) 0.032(2) -0.0103(16) 0.0089(16) -0.0197(18) C10 0.034(2) 0.045(2) 0.038(2) -0.0105(18) 0.0018(16) -0.0138(17) C11 0.035(2) 0.046(2) 0.035(2) -0.0120(17) 0.0013(16) -0.0165(18) C12 0.052(3) 0.054(2) 0.045(2) -0.013(2) 0.0047(19) -0.033(2) C13 0.076(3) 0.043(2) 0.056(3) -0.014(2) 0.007(2) -0.034(2) C14 0.064(3) 0.040(2) 0.050(3) -0.020(2) 0.005(2) -0.020(2) C15 0.045(2) 0.045(2) 0.040(2) -0.0175(18) 0.0057(18) -0.0161(19) C16 0.039(2) 0.039(2) 0.037(2) -0.0084(17) 0.0012(16) -0.0128(17) C17 0.069(3) 0.080(3) 0.053(3) -0.034(3) 0.011(2) -0.018(3) C18 0.079(4) 0.139(6) 0.071(4) -0.064(4) 0.034(3) -0.034(4) C19 0.133(6) 0.127(5) 0.067(4) -0.033(4) 0.047(4) -0.078(5) C20 0.098(4) 0.073(3) 0.050(3) -0.012(3) 0.021(3) -0.041(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 C4 1.209(4) . ? O2 C16 1.230(4) . ? O3 C18 1.411(7) . ? O3 C19 1.433(7) . ? N1 C4 1.366(4) . ? N1 C5 1.460(5) . ? N1 C6 1.435(4) . ? N2 C9 1.433(5) . ? N2 C12 1.471(5) . ? N2 C16 1.346(5) . ? N3 C15 1.421(5) . ? N3 C17 1.453(5) . ? N3 C20 1.452(6) . ? C1 H1A 0.9700 . ? C1 H1B 0.9700 . ? C1 C2 1.469(6) . ? C1 C5 1.471(6) . ? C2 H2A 0.9700 . ? C2 H2B 0.9700 . ? C2 C3 1.495(6) . ? C3 H3A 0.9700 . ? C3 H3B 0.9700 . ? C3 C4 1.508(5) . ? C5 H5A 0.9700 . ? C5 H5B 0.9700 . ? C6 C7 1.384(5) . ? C6 C11 1.374(5) . ? C7 H7 0.9300 . ? C7 C8 1.374(5) . ? C8 H8 0.9300 . ? C8 C9 1.390(5) . ? C9 C10 1.380(5) . ? C10 H10 0.9300 . ? C10 C11 1.387(5) . ? C11 H11 0.9300 . ? C12 H12A 0.9700 . ? C12 H12B 0.9700 . ? C12 C13 1.502(5) . ? C13 H13A 0.9700 . ? C13 H13B 0.9700 . ? C13 C14 1.475(6) . ? C14 H14 0.9300 . ? C14 C15 1.334(5) . ? C15 C16 1.509(5) . ? C17 H17A 0.9700 . ? C17 H17B 0.9700 . ? C17 C18 1.502(7) . ? C18 H18A 0.9700 . ? C18 H18B 0.9700 . ? C19 H19A 0.9700 . ? C19 H19B 0.9700 . ? C19 C20 1.502(7) . ? C20 H20A 0.9700 . ? C20 H20B 0.9700 . ? 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 C18 O3 C19 109.5(4) . . ? C4 N1 C5 124.3(3) . . ? C4 N1 C6 118.9(3) . . ? C6 N1 C5 116.4(3) . . ? C9 N2 C12 118.3(3) . . ? C16 N2 C9 120.2(3) . . ? C16 N2 C12 120.3(3) . . ? C15 N3 C17 115.0(4) . . ? C15 N3 C20 115.2(4) . . ? C20 N3 C17 110.6(4) . . ? H1A C1 H1B 107.6 . . ? C2 C1 H1A 108.6 . . ? C2 C1 H1B 108.6 . . ? C2 C1 C5 114.5(4) . . ? C5 C1 H1A 108.6 . . ? C5 C1 H1B 108.6 . . ? C1 C2 H2A 109.0 . . ? C1 C2 H2B 109.0 . . ? C1 C2 C3 112.7(4) . . ? H2A C2 H2B 107.8 . . ? C3 C2 H2A 109.0 . . ? C3 C2 H2B 109.0 . . ? C2 C3 H3A 108.0 . . ? C2 C3 H3B 108.0 . . ? C2 C3 C4 117.2(3) . . ? H3A C3 H3B 107.3 . . ? C4 C3 H3A 108.0 . . ? C4 C3 H3B 108.0 . . ? O1 C4 N1 122.7(3) . . ? O1 C4 C3 120.0(3) . . ? N1 C4 C3 117.2(3) . . ? N1 C5 C1 114.4(4) . . ? N1 C5 H5A 108.7 . . ? N1 C5 H5B 108.7 . . ? C1 C5 H5A 108.7 . . ? C1 C5 H5B 108.7 . . ? H5A C5 H5B 107.6 . . ? C7 C6 N1 120.0(3) . . ? C11 C6 N1 120.7(3) . . ? C11 C6 C7 119.2(3) . . ? C6 C7 H7 119.7 . . ? C8 C7 C6 120.7(4) . . ? C8 C7 H7 119.7 . . ? C7 C8 H8 119.9 . . ? C7 C8 C9 120.2(4) . . ? C9 C8 H8 119.9 . . ? C8 C9 N2 120.2(4) . . ? C10 C9 N2 120.6(3) . . ? C10 C9 C8 119.1(3) . . ? C9 C10 H10 119.9 . . ? C9 C10 C11 120.3(4) . . ? C11 C10 H10 119.9 . . ? C6 C11 C10 120.5(4) . . ? C6 C11 H11 119.8 . . ? C10 C11 H11 119.8 . . ? N2 C12 H12A 109.8 . . ? N2 C12 H12B 109.8 . . ? N2 C12 C13 109.5(3) . . ? H12A C12 H12B 108.2 . . ? C13 C12 H12A 109.8 . . ? C13 C12 H12B 109.8 . . ? C12 C13 H13A 109.6 . . ? C12 C13 H13B 109.6 . . ? H13A C13 H13B 108.2 . . ? C14 C13 C12 110.1(3) . . ? C14 C13 H13A 109.6 . . ? C14 C13 H13B 109.6 . . ? C13 C14 H14 119.0 . . ? C15 C14 C13 122.0(4) . . ? C15 C14 H14 119.0 . . ? N3 C15 C16 115.1(3) . . ? C14 C15 N3 125.1(4) . . ? C14 C15 C16 119.4(4) . . ? O2 C16 N2 123.0(3) . . ? O2 C16 C15 121.0(3) . . ? N2 C16 C15 116.0(3) . . ? N3 C17 H17A 109.8 . . ? N3 C17 H17B 109.8 . . ? N3 C17 C18 109.5(4) . . ? H17A C17 H17B 108.2 . . ? C18 C17 H17A 109.8 . . ? C18 C17 H17B 109.8 . . ? O3 C18 C17 112.3(5) . . ? O3 C18 H18A 109.1 . . ? O3 C18 H18B 109.1 . . ? C17 C18 H18A 109.1 . . ? C17 C18 H18B 109.1 . . ? H18A C18 H18B 107.9 . . ? O3 C19 H19A 109.6 . . ? O3 C19 H19B 109.6 . . ? O3 C19 C20 110.2(5) . . ? H19A C19 H19B 108.1 . . ? C20 C19 H19A 109.6 . . ? C20 C19 H19B 109.6 . . ? N3 C20 C19 110.9(5) . . ? N3 C20 H20A 109.5 . . ? N3 C20 H20B 109.5 . . ? C19 C20 H20A 109.5 . . ? C19 C20 H20B 109.5 . . ? H20A C20 H20B 108.0 . . ? 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 O3 C19 C20 N3 57.7(7) . . . . ? N1 C6 C7 C8 178.5(3) . . . . ? N1 C6 C11 C10 -178.5(3) . . . . ? N2 C9 C10 C11 -179.7(3) . . . . ? N2 C12 C13 C14 -51.1(5) . . . . ? N3 C15 C16 O2 -9.3(6) . . . . ? N3 C15 C16 N2 172.4(3) . . . . ? N3 C17 C18 O3 -57.6(6) . . . . ? C1 C2 C3 C4 37.7(6) . . . . ? C2 C1 C5 N1 41.8(7) . . . . ? C2 C3 C4 O1 162.4(4) . . . . ? C2 C3 C4 N1 -18.6(6) . . . . ? C4 N1 C5 C1 -22.7(6) . . . . ? C4 N1 C6 C7 57.3(5) . . . . ? C4 N1 C6 C11 -125.3(4) . . . . ? C5 N1 C4 O1 -169.9(4) . . . . ? C5 N1 C4 C3 11.1(6) . . . . ? C5 N1 C6 C7 -130.1(4) . . . . ? C5 N1 C6 C11 47.3(5) . . . . ? C5 C1 C2 C3 -49.6(7) . . . . ? C6 N1 C4 O1 2.1(6) . . . . ? C6 N1 C4 C3 -177.0(4) . . . . ? C6 N1 C5 C1 165.2(4) . . . . ? C6 C7 C8 C9 -1.1(6) . . . . ? C7 C6 C11 C10 -1.1(6) . . . . ? C7 C8 C9 N2 179.7(3) . . . . ? C7 C8 C9 C10 1.1(6) . . . . ? C8 C9 C10 C11 -1.1(6) . . . . ? C9 N2 C12 C13 -144.3(4) . . . . ? C9 N2 C16 O2 -0.2(6) . . . . ? C9 N2 C16 C15 178.0(3) . . . . ? C9 C10 C11 C6 1.1(6) . . . . ? C11 C6 C7 C8 1.1(6) . . . . ? C12 N2 C9 C8 -41.9(5) . . . . ? C12 N2 C9 C10 136.6(4) . . . . ? C12 N2 C16 O2 167.2(4) . . . . ? C12 N2 C16 C15 -14.6(5) . . . . ? C12 C13 C14 C15 26.0(6) . . . . ? C13 C14 C15 N3 179.6(4) . . . . ? C13 C14 C15 C16 7.9(7) . . . . ? C14 C15 C16 O2 163.2(4) . . . . ? C14 C15 C16 N2 -15.1(6) . . . . ? C15 N3 C17 C18 -173.0(4) . . . . ? C15 N3 C20 C19 171.8(4) . . . . ? C16 N2 C9 C8 125.8(4) . . . . ? C16 N2 C9 C10 -55.7(5) . . . . ? C16 N2 C12 C13 48.1(5) . . . . ? C17 N3 C15 C14 -5.8(6) . . . . ? C17 N3 C15 C16 166.3(4) . . . . ? C17 N3 C20 C19 -55.7(6) . . . . ? C18 O3 C19 C20 -59.0(7) . . . . ? C19 O3 C18 C17 59.8(6) . . . . ? C20 N3 C15 C14 124.7(5) . . . . ? C20 N3 C15 C16 -63.2(5) . . . . ? C20 N3 C17 C18 54.4(6) . . . . ? _olex2_submission_special_instructions 'No special instructions were received'