# Electronic Supplementary Material (ESI) for Organic & Biomolecular Chemistry # This journal is © The Royal Society of Chemistry 2011 data_global _journal_name_full Org.Biomol.Chem. _journal_coden_cambridge 0177 _journal_year ? _journal_volume ? _journal_page_first ? _publ_contact_author_email xyliu100@126.com _publ_contact_author_name 'Xiao-Yu Liu' loop_ _publ_author_name 'Liu, Xiao-Yu' 'Chen, Hang' 'Li, Xiao-Huan' 'Chen, Qiao-Hong' 'Xu, Liang' 'Wang, Feng-Peng' data_201107110 _database_code_depnum_ccdc_archive 'CCDC 834603' #TrackingRef 'web_deposit_cif_file_0_Xiao-YuLiu_1310953464.201107110.cif' _audit_creation_date 2011-07-16 _audit_creation_method ; Olex2 1.1 (compiled 2011.02.15 svn.r1672, GUI svn.r3494) ; _chemical_name_common ? _chemical_name_systematic ; ? ; _chemical_formula_moiety 'C22 H33 N O2' _chemical_formula_sum 'C22 H33 N O2' _chemical_formula_weight 343.49 _chemical_melting_point ? _chemical_oxdiff_formula 'C11 H10 S O2' loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0181 0.0091 '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 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _space_group_crystal_system orthorhombic _space_group_IT_number 61 _space_group_name_H-M_alt 'P b c a' _space_group_name_Hall '-P 2ac 2ab' loop_ _space_group_symop_id _space_group_symop_operation_xyz 1 'x, y, z' 2 '-x+1/2, -y, z+1/2' 3 'x+1/2, -y+1/2, -z' 4 '-x, y+1/2, -z+1/2' 5 '-x, -y, -z' 6 'x-1/2, y, -z-1/2' 7 '-x-1/2, y-1/2, z' 8 'x, -y-1/2, z-1/2' _cell_length_a 8.4693(8) _cell_length_b 19.713(3) _cell_length_c 22.265(2) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 3717.2(7) _cell_formula_units_Z 8 _cell_measurement_reflns_used 3726 _cell_measurement_temperature 291.15 _cell_measurement_theta_max 66.9667 _cell_measurement_theta_min 2.9927 _exptl_absorpt_coefficient_mu 0.598 _exptl_absorpt_correction_T_max 1.00000 _exptl_absorpt_correction_T_min 0.65886 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details ; CrysAlisPro, Agilent Technologies, Version 1.171.35.11 (release 16-05-2011 CrysAlis171 .NET) (compiled May 16 2011,17:55:39) Empirical absorption correction using spherical harmonics, implemented in SCALE3 ABSPACK scaling algorithm. ; _exptl_crystal_colour ? _exptl_crystal_density_diffrn 1.228 _exptl_crystal_density_meas ? _exptl_crystal_density_method 'not measured' _exptl_crystal_description ? _exptl_crystal_F_000 1504 _exptl_crystal_size_max 0.20 _exptl_crystal_size_mid 0.18 _exptl_crystal_size_min 0.18 _exptl_special_details ; ? ; _diffrn_reflns_av_R_equivalents 0.0308 _diffrn_reflns_av_unetI/netI 0.0251 _diffrn_reflns_limit_h_max 6 _diffrn_reflns_limit_h_min -10 _diffrn_reflns_limit_k_max 23 _diffrn_reflns_limit_k_min -17 _diffrn_reflns_limit_l_max 26 _diffrn_reflns_limit_l_min -25 _diffrn_reflns_number 12837 _diffrn_reflns_theta_full 67.08 _diffrn_reflns_theta_max 67.08 _diffrn_reflns_theta_min 3.97 _diffrn_ambient_temperature 291.15 _diffrn_detector_area_resol_mean 16.2312 _diffrn_measured_fraction_theta_full 0.998 _diffrn_measured_fraction_theta_max 0.998 _diffrn_measurement_details ; #__ type_ start__ end____ width___ exp.time_ 1 omega -29.00 18.00 1.0000 1.5000 omega____ theta____ kappa____ phi______ frames - 0.0000 77.0000 120.0000 47 #__ type_ start__ end____ width___ exp.time_ 2 omega 35.00 69.00 1.0000 1.5000 omega____ theta____ kappa____ phi______ frames - 0.0000 77.0000 120.0000 34 #__ type_ start__ end____ width___ exp.time_ 3 omega -95.00 -62.00 1.0000 10.0000 omega____ theta____ kappa____ phi______ frames - -42.5000 -50.0000 -180.0000 33 #__ type_ start__ end____ width___ exp.time_ 4 omega -83.00 -47.00 1.0000 10.0000 omega____ theta____ kappa____ phi______ frames - -42.5000 -162.0000 -76.0000 36 #__ type_ start__ end____ width___ exp.time_ 5 omega -51.00 26.00 1.0000 10.0000 omega____ theta____ kappa____ phi______ frames - -42.5000 25.0000 -150.0000 77 #__ type_ start__ end____ width___ exp.time_ 6 omega 86.00 124.00 1.0000 10.0000 omega____ theta____ kappa____ phi______ frames - 55.8596 162.0000 -48.0000 38 #__ type_ start__ end____ width___ exp.time_ 7 omega -5.00 84.00 1.0000 10.0000 omega____ theta____ kappa____ phi______ frames - 55.8596 -77.0000 60.0000 89 #__ type_ start__ end____ width___ exp.time_ 8 omega 40.00 93.00 1.0000 60.0000 omega____ theta____ kappa____ phi______ frames - 111.7191 -25.0000 -30.0000 53 #__ type_ start__ end____ width___ exp.time_ 9 omega 43.00 80.00 1.0000 60.0000 omega____ theta____ kappa____ phi______ frames - 111.7191 -117.0000 73.0000 37 #__ type_ start__ end____ width___ exp.time_ 10 omega 45.00 104.00 1.0000 60.0000 omega____ theta____ kappa____ phi______ frames - 111.7191 -50.0000 90.0000 59 #__ type_ start__ end____ width___ exp.time_ 11 omega 45.00 94.00 1.0000 60.0000 omega____ theta____ kappa____ phi______ frames - 111.7191 -25.0000 90.0000 49 #__ type_ start__ end____ width___ exp.time_ 12 omega 60.00 118.00 1.0000 60.0000 omega____ theta____ kappa____ phi______ frames - 111.7191 -119.0000 -71.0000 58 #__ type_ start__ end____ width___ exp.time_ 13 omega 43.00 70.00 1.0000 60.0000 omega____ theta____ kappa____ phi______ frames - 111.7191 -25.0000 -180.0000 27 #__ type_ start__ end____ width___ exp.time_ 14 omega 41.00 88.00 1.0000 60.0000 omega____ theta____ kappa____ phi______ frames - 111.7191 -25.0000 30.0000 47 #__ type_ start__ end____ width___ exp.time_ 15 omega 110.00 143.00 1.0000 60.0000 omega____ theta____ kappa____ phi______ frames - 111.7191 162.0000 -48.0000 33 #__ type_ start__ end____ width___ exp.time_ 16 omega 42.00 104.00 1.0000 60.0000 omega____ theta____ kappa____ phi______ frames - 111.7191 -50.0000 -180.0000 62 #__ type_ start__ end____ width___ exp.time_ 17 omega 91.00 178.00 1.0000 60.0000 omega____ theta____ kappa____ phi______ frames - 111.7191 0.0000 0.0000 87 #__ type_ start__ end____ width___ exp.time_ 18 omega -30.00 70.00 1.0000 1.5000 omega____ theta____ kappa____ phi______ frames - 0.0000 77.0000 -90.0000 100 #__ type_ start__ end____ width___ exp.time_ 19 omega 26.00 77.00 1.0000 10.0000 omega____ theta____ kappa____ phi______ frames - 55.8596 77.0000 60.0000 51 ; _diffrn_measurement_device_type 'Xcalibur, Eos, Gemini' _diffrn_measurement_method '\w scans' _diffrn_orient_matrix_UB_11 0.0389296000 _diffrn_orient_matrix_UB_12 -0.0677163000 _diffrn_orient_matrix_UB_13 0.0313614000 _diffrn_orient_matrix_UB_21 0.0140941000 _diffrn_orient_matrix_UB_22 0.0371598000 _diffrn_orient_matrix_UB_23 0.0606369000 _diffrn_orient_matrix_UB_31 -0.1771911000 _diffrn_orient_matrix_UB_32 -0.0118518000 _diffrn_orient_matrix_UB_33 0.0116758000 _diffrn_radiation_monochromator graphite _diffrn_radiation_type 'Cu K\a' _diffrn_radiation_wavelength 1.5418 _diffrn_source 'Enhance (Cu) X-ray Source' _diffrn_standards_decay_% ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_number ? _reflns_number_gt 2623 _reflns_number_total 3311 _reflns_odcompleteness_completeness 99.87 _reflns_odcompleteness_iscentric 1 _reflns_odcompleteness_theta 66.97 _reflns_threshold_expression >2sigma(I) _computing_cell_refinement ; CrysAlisPro, Agilent Technologies, Version 1.171.35.11 (release 16-05-2011 CrysAlis171 .NET) (compiled May 16 2011,17:55:39) ; _computing_data_collection ; CrysAlisPro, Agilent Technologies, Version 1.171.35.11 (release 16-05-2011 CrysAlis171 .NET) (compiled May 16 2011,17:55:39) ; _computing_data_reduction ; CrysAlisPro, Agilent Technologies, Version 1.171.35.11 (release 16-05-2011 CrysAlis171 .NET) (compiled May 16 2011,17:55:39) ; _computing_molecular_graphics ; O. V. Dolomanov, L. J. Bourhis, R. J. Gildea, J. A. K. Howard and H. Puschmann, OLEX2: a complete structure solution, refinement and analysis program. J. Appl. Cryst. (2009). 42, 339-341. ; _computing_publication_material ; O. V. Dolomanov, L. J. Bourhis, R. J. Gildea, J. A. K. Howard and H. Puschmann, OLEX2: a complete structure solution, refinement and analysis program. J. Appl. Cryst. (2009). 42, 339-341. ; _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_structure_solution 'A short history of SHELX (Sheldrick, 2007)' _refine_diff_density_max 0.258 _refine_diff_density_min -0.167 _refine_diff_density_rms 0.036 _refine_ls_extinction_coef ? _refine_ls_extinction_method none _refine_ls_goodness_of_fit_ref 1.041 _refine_ls_hydrogen_treatment mixed _refine_ls_matrix_type full _refine_ls_number_parameters 232 _refine_ls_number_reflns 3311 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0584 _refine_ls_R_factor_gt 0.0451 _refine_ls_restrained_S_all 1.041 _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^)+(0.0688P)^2^+0.7129P] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_gt 0.1200 _refine_ls_wR_factor_ref 0.1290 _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. ; _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_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group O1 O 0.04908(18) 0.60878(7) 0.62087(9) 0.0660(5) Uani 1 1 d . . . O2 O 0.22529(15) 0.19824(7) 0.67343(7) 0.0529(4) Uani 1 1 d . . . N1 N -0.00235(17) 0.25705(7) 0.67587(7) 0.0398(3) Uani 1 1 d . . . C1 C -0.0132(2) 0.30861(10) 0.54586(8) 0.0441(4) Uani 1 1 d . . . H1A H -0.0561 0.3345 0.5126 0.053 Uiso 1 1 calc R . . H1B H 0.0956 0.2978 0.5361 0.053 Uiso 1 1 calc R . . C2 C -0.1059(2) 0.24227(10) 0.55122(9) 0.0487(5) Uani 1 1 d . . . H2A H -0.0447 0.2100 0.5745 0.058 Uiso 1 1 calc R . . H2B H -0.1213 0.2233 0.5115 0.058 Uiso 1 1 calc R . . C3 C -0.2668(2) 0.25223(10) 0.58118(9) 0.0477(4) Uani 1 1 d . . . H3A H -0.3091 0.2081 0.5918 0.057 Uiso 1 1 calc R . . H3B H -0.3383 0.2726 0.5523 0.057 Uiso 1 1 calc R . . C4 C -0.26380(19) 0.29688(9) 0.63801(8) 0.0385(4) Uani 1 1 d . . . C5 C -0.18843(18) 0.36585(8) 0.62123(7) 0.0337(4) Uani 1 1 d . . . H5 H -0.2438 0.3820 0.5853 0.040 Uiso 1 1 calc R . . C6 C -0.20386(19) 0.42196(9) 0.66841(8) 0.0399(4) Uani 1 1 d . . . H6A H -0.3145 0.4283 0.6782 0.048 Uiso 1 1 calc R . . H6B H -0.1493 0.4082 0.7047 0.048 Uiso 1 1 calc R . . C7 C -0.1351(2) 0.48890(9) 0.64620(9) 0.0428(4) Uani 1 1 d . . . H7A H -0.1458 0.5227 0.6776 0.051 Uiso 1 1 calc R . . H7B H -0.1956 0.5043 0.6118 0.051 Uiso 1 1 calc R . . C8 C 0.03853(19) 0.48363(8) 0.62835(7) 0.0358(4) Uani 1 1 d . . . C9 C 0.06081(19) 0.42275(8) 0.58462(7) 0.0344(4) Uani 1 1 d . . . H9 H 0.0043 0.4363 0.5481 0.041 Uiso 1 1 calc R . . C10 C -0.01463(18) 0.35380(8) 0.60249(7) 0.0327(3) Uani 1 1 d . . . C11 C 0.2367(2) 0.41774(10) 0.56479(8) 0.0440(4) Uani 1 1 d . . . H11A H 0.2786 0.3736 0.5756 0.053 Uiso 1 1 calc R . . H11B H 0.2440 0.4226 0.5215 0.053 Uiso 1 1 calc R . . C12 C 0.3334(2) 0.47337(10) 0.59543(9) 0.0467(4) Uani 1 1 d . . . H12 H 0.4444 0.4703 0.5833 0.056 Uiso 1 1 calc R . . C13 C 0.3182(2) 0.46427(10) 0.66344(9) 0.0463(4) Uani 1 1 d . . . H13A H 0.3928 0.4936 0.6838 0.056 Uiso 1 1 calc R . . H13B H 0.3421 0.4177 0.6742 0.056 Uiso 1 1 calc R . . C14 C 0.1491(2) 0.48194(9) 0.68316(8) 0.0406(4) Uani 1 1 d . . . H14A H 0.1485 0.5258 0.7028 0.049 Uiso 1 1 calc R . . H14B H 0.1117 0.4484 0.7117 0.049 Uiso 1 1 calc R . . C15 C 0.0901(2) 0.54717(9) 0.59189(9) 0.0459(4) Uani 1 1 d . . . H15 H 0.0335 0.5459 0.5535 0.055 Uiso 1 1 calc R . . C16 C 0.2658(2) 0.54147(10) 0.57789(9) 0.0484(4) Uani 1 1 d . . . C17 C 0.3484(3) 0.59057(12) 0.55270(11) 0.0657(6) Uani 1 1 d . . . H17A H 0.4552 0.5843 0.5447 0.079 Uiso 1 1 calc R . . H17B H 0.2998 0.6314 0.5429 0.079 Uiso 1 1 calc R . . C18 C -0.4348(2) 0.30455(11) 0.65962(10) 0.0516(5) Uani 1 1 d . . . H18A H -0.4939 0.3301 0.6306 0.077 Uiso 1 1 calc R . . H18B H -0.4361 0.3279 0.6975 0.077 Uiso 1 1 calc R . . H18C H -0.4814 0.2605 0.6643 0.077 Uiso 1 1 calc R . . C19 C -0.1711(2) 0.26384(10) 0.68951(9) 0.0439(4) Uani 1 1 d . . . H19A H -0.1836 0.2910 0.7255 0.053 Uiso 1 1 calc R . . H19B H -0.2148 0.2193 0.6976 0.053 Uiso 1 1 calc R . . C20 C 0.07552(19) 0.31864(9) 0.65413(8) 0.0380(4) Uani 1 1 d . . . H20A H 0.1808 0.3071 0.6403 0.046 Uiso 1 1 calc R . . H20B H 0.0863 0.3503 0.6873 0.046 Uiso 1 1 calc R . . C21 C 0.0831(2) 0.20079(9) 0.68589(8) 0.0413(4) Uani 1 1 d . . . C22 C 0.0032(3) 0.14008(11) 0.71308(11) 0.0625(6) Uani 1 1 d . . . H22A H -0.0742 0.1228 0.6856 0.094 Uiso 1 1 calc R . . H22B H -0.0476 0.1531 0.7499 0.094 Uiso 1 1 calc R . . H22C H 0.0803 0.1056 0.7212 0.094 Uiso 1 1 calc R . . H1 H 0.134(4) 0.6304(18) 0.6372(15) 0.109(11) 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 O1 0.0515(8) 0.0339(7) 0.1125(13) -0.0043(8) -0.0127(8) 0.0026(6) O2 0.0410(7) 0.0419(7) 0.0758(9) -0.0036(6) -0.0049(6) 0.0111(6) N1 0.0337(7) 0.0353(8) 0.0503(8) 0.0051(6) 0.0004(6) 0.0027(6) C1 0.0407(9) 0.0477(10) 0.0439(9) -0.0138(8) 0.0061(7) -0.0020(8) C2 0.0479(10) 0.0439(10) 0.0542(11) -0.0171(8) 0.0005(8) -0.0022(8) C3 0.0398(9) 0.0432(10) 0.0602(11) -0.0087(9) -0.0023(8) -0.0078(8) C4 0.0287(8) 0.0407(9) 0.0459(9) 0.0001(7) 0.0016(7) 0.0009(7) C5 0.0287(8) 0.0376(9) 0.0350(8) -0.0008(6) -0.0010(6) 0.0040(6) C6 0.0327(8) 0.0450(10) 0.0420(9) -0.0064(7) 0.0045(7) 0.0066(7) C7 0.0394(9) 0.0361(9) 0.0530(10) -0.0088(8) -0.0028(8) 0.0096(7) C8 0.0359(9) 0.0324(9) 0.0389(8) -0.0016(7) -0.0036(7) 0.0036(6) C9 0.0346(8) 0.0373(9) 0.0313(7) -0.0007(6) -0.0006(6) 0.0019(7) C10 0.0305(8) 0.0338(8) 0.0338(8) -0.0032(6) 0.0017(6) 0.0018(6) C11 0.0421(9) 0.0439(10) 0.0462(9) -0.0045(8) 0.0099(8) -0.0038(8) C12 0.0339(9) 0.0428(10) 0.0634(11) -0.0016(9) 0.0046(8) -0.0033(7) C13 0.0389(9) 0.0408(10) 0.0592(11) -0.0021(8) -0.0115(8) 0.0036(7) C14 0.0443(10) 0.0358(9) 0.0417(9) -0.0043(7) -0.0078(7) 0.0034(7) C15 0.0481(10) 0.0353(9) 0.0543(10) 0.0059(8) -0.0109(8) -0.0012(8) C16 0.0514(11) 0.0429(10) 0.0507(10) 0.0004(8) -0.0031(8) -0.0085(8) C17 0.0675(14) 0.0558(13) 0.0736(14) 0.0114(11) 0.0022(11) -0.0125(11) C18 0.0321(9) 0.0554(12) 0.0674(12) 0.0017(9) 0.0055(8) 0.0000(8) C19 0.0364(9) 0.0428(10) 0.0524(10) 0.0090(8) 0.0069(7) 0.0003(7) C20 0.0295(8) 0.0358(9) 0.0487(9) 0.0024(7) -0.0019(7) 0.0017(6) C21 0.0439(10) 0.0353(9) 0.0446(9) -0.0028(7) -0.0053(7) 0.0050(7) C22 0.0694(14) 0.0370(10) 0.0812(15) 0.0117(10) 0.0052(12) 0.0061(9) _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 C15 1.418(2) . ? O1 H1 0.92(3) . ? O2 C21 1.237(2) . ? N1 C19 1.467(2) . ? N1 C20 1.464(2) . ? N1 C21 1.343(2) . ? C1 H1A 0.9700 . ? C1 H1B 0.9700 . ? C1 C2 1.530(3) . ? C1 C10 1.544(2) . ? C2 H2A 0.9700 . ? C2 H2B 0.9700 . ? C2 C3 1.530(3) . ? C3 H3A 0.9700 . ? C3 H3B 0.9700 . ? C3 C4 1.541(3) . ? C4 C5 1.548(2) . ? C4 C18 1.533(2) . ? C4 C19 1.535(2) . ? C5 H5 0.9800 . ? C5 C6 1.531(2) . ? C5 C10 1.548(2) . ? C6 H6A 0.9700 . ? C6 H6B 0.9700 . ? C6 C7 1.525(3) . ? C7 H7A 0.9700 . ? C7 H7B 0.9700 . ? C7 C8 1.527(2) . ? C8 C9 1.557(2) . ? C8 C14 1.538(2) . ? C8 C15 1.555(2) . ? C9 H9 0.9800 . ? C9 C10 1.554(2) . ? C9 C11 1.557(2) . ? C10 C20 1.544(2) . ? C11 H11A 0.9700 . ? C11 H11B 0.9700 . ? C11 C12 1.530(3) . ? C12 H12 0.9800 . ? C12 C13 1.530(3) . ? C12 C16 1.511(3) . ? C13 H13A 0.9700 . ? C13 H13B 0.9700 . ? C13 C14 1.538(3) . ? C14 H14A 0.9700 . ? C14 H14B 0.9700 . ? C15 H15 0.9800 . ? C15 C16 1.524(3) . ? C16 C17 1.319(3) . ? C17 H17A 0.9300 . ? C17 H17B 0.9300 . ? C18 H18A 0.9600 . ? C18 H18B 0.9600 . ? C18 H18C 0.9600 . ? C19 H19A 0.9700 . ? C19 H19B 0.9700 . ? C20 H20A 0.9700 . ? C20 H20B 0.9700 . ? C21 C22 1.502(3) . ? C22 H22A 0.9600 . ? C22 H22B 0.9600 . ? C22 H22C 0.9600 . ? 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 C15 O1 H1 113(2) . . ? C20 N1 C19 115.57(14) . . ? C21 N1 C19 124.46(15) . . ? C21 N1 C20 119.80(15) . . ? H1A C1 H1B 107.5 . . ? C2 C1 H1A 108.5 . . ? C2 C1 H1B 108.5 . . ? C2 C1 C10 115.18(15) . . ? C10 C1 H1A 108.5 . . ? C10 C1 H1B 108.5 . . ? C1 C2 H2A 109.1 . . ? C1 C2 H2B 109.1 . . ? C1 C2 C3 112.42(15) . . ? H2A C2 H2B 107.9 . . ? C3 C2 H2A 109.1 . . ? C3 C2 H2B 109.1 . . ? C2 C3 H3A 108.6 . . ? C2 C3 H3B 108.6 . . ? C2 C3 C4 114.60(15) . . ? H3A C3 H3B 107.6 . . ? C4 C3 H3A 108.6 . . ? C4 C3 H3B 108.6 . . ? C3 C4 C5 108.08(14) . . ? C18 C4 C3 107.34(15) . . ? C18 C4 C5 112.24(15) . . ? C18 C4 C19 106.89(15) . . ? C19 C4 C3 112.31(15) . . ? C19 C4 C5 110.01(14) . . ? C4 C5 H5 106.5 . . ? C4 C5 C10 108.80(13) . . ? C6 C5 C4 115.71(14) . . ? C6 C5 H5 106.5 . . ? C6 C5 C10 112.15(13) . . ? C10 C5 H5 106.5 . . ? C5 C6 H6A 109.3 . . ? C5 C6 H6B 109.3 . . ? H6A C6 H6B 107.9 . . ? C7 C6 C5 111.72(14) . . ? C7 C6 H6A 109.3 . . ? C7 C6 H6B 109.3 . . ? C6 C7 H7A 108.9 . . ? C6 C7 H7B 108.9 . . ? C6 C7 C8 113.16(14) . . ? H7A C7 H7B 107.8 . . ? C8 C7 H7A 108.9 . . ? C8 C7 H7B 108.9 . . ? C7 C8 C9 109.39(14) . . ? C7 C8 C14 112.40(15) . . ? C7 C8 C15 110.58(14) . . ? C14 C8 C9 113.94(13) . . ? C14 C8 C15 105.10(14) . . ? C15 C8 C9 105.08(14) . . ? C8 C9 H9 104.4 . . ? C10 C9 C8 117.66(13) . . ? C10 C9 H9 104.4 . . ? C10 C9 C11 114.24(14) . . ? C11 C9 C8 110.02(13) . . ? C11 C9 H9 104.4 . . ? C1 C10 C5 108.43(13) . . ? C1 C10 C9 107.01(13) . . ? C1 C10 C20 110.19(14) . . ? C5 C10 C9 109.01(13) . . ? C20 C10 C5 109.76(13) . . ? C20 C10 C9 112.33(13) . . ? C9 C11 H11A 109.7 . . ? C9 C11 H11B 109.7 . . ? H11A C11 H11B 108.2 . . ? C12 C11 C9 109.91(14) . . ? C12 C11 H11A 109.7 . . ? C12 C11 H11B 109.7 . . ? C11 C12 H12 110.3 . . ? C11 C12 C13 108.18(15) . . ? C13 C12 H12 110.3 . . ? C16 C12 C11 108.57(16) . . ? C16 C12 H12 110.3 . . ? C16 C12 C13 109.14(16) . . ? C12 C13 H13A 109.8 . . ? C12 C13 H13B 109.8 . . ? C12 C13 C14 109.53(14) . . ? H13A C13 H13B 108.2 . . ? C14 C13 H13A 109.8 . . ? C14 C13 H13B 109.8 . . ? C8 C14 H14A 109.6 . . ? C8 C14 H14B 109.6 . . ? C13 C14 C8 110.20(14) . . ? C13 C14 H14A 109.6 . . ? C13 C14 H14B 109.6 . . ? H14A C14 H14B 108.1 . . ? O1 C15 C8 112.54(16) . . ? O1 C15 H15 107.3 . . ? O1 C15 C16 113.28(16) . . ? C8 C15 H15 107.3 . . ? C16 C15 C8 108.75(15) . . ? C16 C15 H15 107.3 . . ? C12 C16 C15 112.52(16) . . ? C17 C16 C12 124.1(2) . . ? C17 C16 C15 123.4(2) . . ? C16 C17 H17A 120.0 . . ? C16 C17 H17B 120.0 . . ? H17A C17 H17B 120.0 . . ? C4 C18 H18A 109.5 . . ? C4 C18 H18B 109.5 . . ? C4 C18 H18C 109.5 . . ? H18A C18 H18B 109.5 . . ? H18A C18 H18C 109.5 . . ? H18B C18 H18C 109.5 . . ? N1 C19 C4 112.48(14) . . ? N1 C19 H19A 109.1 . . ? N1 C19 H19B 109.1 . . ? C4 C19 H19A 109.1 . . ? C4 C19 H19B 109.1 . . ? H19A C19 H19B 107.8 . . ? N1 C20 C10 113.31(13) . . ? N1 C20 H20A 108.9 . . ? N1 C20 H20B 108.9 . . ? C10 C20 H20A 108.9 . . ? C10 C20 H20B 108.9 . . ? H20A C20 H20B 107.7 . . ? O2 C21 N1 121.40(17) . . ? O2 C21 C22 119.79(17) . . ? N1 C21 C22 118.81(17) . . ? C21 C22 H22A 109.5 . . ? C21 C22 H22B 109.5 . . ? C21 C22 H22C 109.5 . . ? H22A C22 H22B 109.5 . . ? H22A C22 H22C 109.5 . . ? H22B C22 H22C 109.5 . . ? 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 O1 H1 O2 0.92(3) 1.96(3) 2.852(2) 164(3) 7_665 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 O1 C15 C16 C12 133.55(17) . . . . ? O1 C15 C16 C17 -47.1(3) . . . . ? C1 C2 C3 C4 -45.3(2) . . . . ? C1 C10 C20 N1 -66.65(18) . . . . ? C2 C1 C10 C5 -53.4(2) . . . . ? C2 C1 C10 C9 -170.82(15) . . . . ? C2 C1 C10 C20 66.78(19) . . . . ? C2 C3 C4 C5 55.6(2) . . . . ? C2 C3 C4 C18 176.82(17) . . . . ? C2 C3 C4 C19 -66.0(2) . . . . ? C3 C4 C5 C6 168.60(14) . . . . ? C3 C4 C5 C10 -64.10(16) . . . . ? C3 C4 C19 N1 65.8(2) . . . . ? C4 C5 C6 C7 -176.49(13) . . . . ? C4 C5 C10 C1 62.94(17) . . . . ? C4 C5 C10 C9 179.11(12) . . . . ? C4 C5 C10 C20 -57.48(17) . . . . ? C5 C4 C19 N1 -54.6(2) . . . . ? C5 C6 C7 C8 -57.77(19) . . . . ? C5 C10 C20 N1 52.69(18) . . . . ? C6 C5 C10 C1 -167.76(14) . . . . ? C6 C5 C10 C9 -51.59(17) . . . . ? C6 C5 C10 C20 71.82(18) . . . . ? C6 C7 C8 C9 50.77(19) . . . . ? C6 C7 C8 C14 -76.85(18) . . . . ? C6 C7 C8 C15 166.03(14) . . . . ? C7 C8 C9 C10 -48.16(19) . . . . ? C7 C8 C9 C11 178.66(14) . . . . ? C7 C8 C14 C13 170.21(15) . . . . ? C7 C8 C15 O1 50.73(19) . . . . ? C7 C8 C15 C16 177.09(15) . . . . ? C8 C9 C10 C1 165.71(14) . . . . ? C8 C9 C10 C5 48.63(18) . . . . ? C8 C9 C10 C20 -73.24(18) . . . . ? C8 C9 C11 C12 1.1(2) . . . . ? C8 C15 C16 C12 7.6(2) . . . . ? C8 C15 C16 C17 -173.0(2) . . . . ? C9 C8 C14 C13 45.0(2) . . . . ? C9 C8 C15 O1 168.67(14) . . . . ? C9 C8 C15 C16 -64.97(17) . . . . ? C9 C10 C20 N1 174.14(13) . . . . ? C9 C11 C12 C13 58.99(19) . . . . ? C9 C11 C12 C16 -59.33(19) . . . . ? C10 C1 C2 C3 44.2(2) . . . . ? C10 C5 C6 C7 57.90(18) . . . . ? C10 C9 C11 C12 -133.82(15) . . . . ? C11 C9 C10 C1 -63.00(17) . . . . ? C11 C9 C10 C5 179.93(13) . . . . ? C11 C9 C10 C20 58.06(18) . . . . ? C11 C12 C13 C14 -69.50(19) . . . . ? C11 C12 C16 C15 55.1(2) . . . . ? C11 C12 C16 C17 -124.3(2) . . . . ? C12 C13 C14 C8 15.7(2) . . . . ? C13 C12 C16 C15 -62.6(2) . . . . ? C13 C12 C16 C17 118.0(2) . . . . ? C14 C8 C9 C10 78.60(18) . . . . ? C14 C8 C9 C11 -54.59(19) . . . . ? C14 C8 C15 O1 -70.80(18) . . . . ? C14 C8 C15 C16 55.55(18) . . . . ? C15 C8 C9 C10 -166.90(14) . . . . ? C15 C8 C9 C11 59.92(16) . . . . ? C15 C8 C14 C13 -69.45(17) . . . . ? C16 C12 C13 C14 48.5(2) . . . . ? C18 C4 C5 C6 50.4(2) . . . . ? C18 C4 C5 C10 177.72(14) . . . . ? C18 C4 C19 N1 -176.76(15) . . . . ? C19 N1 C20 C10 -49.4(2) . . . . ? C19 N1 C21 O2 -179.96(17) . . . . ? C19 N1 C21 C22 -0.2(3) . . . . ? C19 C4 C5 C6 -68.46(18) . . . . ? C19 C4 C5 C10 58.84(17) . . . . ? C20 N1 C19 C4 50.2(2) . . . . ? C20 N1 C21 O2 -4.8(3) . . . . ? C20 N1 C21 C22 174.92(17) . . . . ? C21 N1 C19 C4 -134.49(18) . . . . ? C21 N1 C20 C10 135.05(16) . . . . ?