# Supplementary Material (ESI) for ChemComm # This journal is © The Royal Society of Chemistry 1999 # CCDC Number: 182/1471 #========== data_global #========== _publ_contact_author ; Christopher S. Frampton Department Physical Methods Roche Discovery Welwyn Welwyn Garden City Hertfordshire AL7 3AY U.K. ; _publ_contact_author_phone '44(1707)366272' _publ_contact_author_fax '44(1707)366907' _publ_contact_author_email 'christopher.frampton@roche.com' _publ_requested_journal 'Angewandte Chemie' data_csf104a _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C20 H32 N2 O6' _chemical_formula_sum 'C20 H32 N2 O6' _chemical_formula_weight 396.48 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' 'N' 'N' 0.0311 0.0180 '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' _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M 'P 21' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y+1/2, -z' _cell_length_a 6.332(4) _cell_length_b 26.000(4) _cell_length_c 6.720(3) _cell_angle_alpha 90.00 _cell_angle_beta 112.63(4) _cell_angle_gamma 90.00 _cell_volume 1021.1(8) _cell_formula_units_Z 2 _cell_measurement_temperature 123(1) _cell_measurement_reflns_used 25 _cell_measurement_theta_min 53.1 _cell_measurement_theta_max 54.9 _exptl_crystal_description prism _exptl_crystal_colour colorless _exptl_crystal_size_max 0.400 _exptl_crystal_size_mid 0.350 _exptl_crystal_size_min 0.300 _exptl_crystal_density_meas 'not measured' _exptl_crystal_density_diffrn 1.289 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 428 _exptl_absorpt_coefficient_mu 0.781 _exptl_absorpt_correction_type '\y scans(North,Phillips & Mathews,1968)' _exptl_absorpt_correction_T_min 0.916 _exptl_absorpt_correction_T_max 0.999 _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 123(1) _diffrn_radiation_wavelength 1.54178 _diffrn_radiation_type CuK\a _diffrn_radiation_source 'Rigaku RU200 Rotating Cu Anode' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Rigaku AFC7R' _diffrn_measurement_method \w-2\q _diffrn_detector_area_resol_mean ? _diffrn_standards_number 3 _diffrn_standards_interval_count 150 _diffrn_standards_interval_time ? _diffrn_standards_decay_% 2.32 _diffrn_reflns_number 4008 _diffrn_reflns_av_R_equivalents 0.0140 _diffrn_reflns_av_sigmaI/netI 0.0087 _diffrn_reflns_limit_h_min -7 _diffrn_reflns_limit_h_max 7 _diffrn_reflns_limit_k_min -31 _diffrn_reflns_limit_k_max 31 _diffrn_reflns_limit_l_min -7 _diffrn_reflns_limit_l_max 7 _diffrn_reflns_theta_min 3.40 _diffrn_reflns_theta_max 67.45 _reflns_number_total 3589 _reflns_number_gt 3585 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Rigaku/AFC Diffractometer Control' _computing_cell_refinement 'Rigaku/AFC Diffractometer Control' _computing_data_reduction 'teXsan' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics ? _computing_publication_material ? _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^)+(0.0850P)^2^+0.4000P] 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 none _refine_ls_extinction_coef ? _refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881' _refine_ls_abs_structure_Flack 0.14(19) _refine_ls_number_reflns 3589 _refine_ls_number_parameters 295 _refine_ls_number_restraints 1 _refine_ls_R_factor_all 0.0418 _refine_ls_R_factor_gt 0.0417 _refine_ls_wR_factor_ref 0.1177 _refine_ls_wR_factor_gt 0.1177 _refine_ls_goodness_of_fit_ref 1.009 _refine_ls_restrained_S_all 1.008 _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 0.6381(3) 0.79456(7) 0.5243(3) 0.0309(4) Uani 1 1 d . . . H1B H 0.636(4) 0.8201(11) 0.605(4) 0.023(6) Uiso 1 1 d . . . O2 O -0.2069(3) 0.68156(6) -0.0908(3) 0.0319(4) Uani 1 1 d . . . O3 O 0.3960(3) 0.86265(6) 0.6459(3) 0.0339(4) Uani 1 1 d . . . O4 O 0.0180(3) 0.85976(6) 0.4204(3) 0.0311(4) Uani 1 1 d . . . O5 O 0.0767(3) 0.61186(7) -0.1617(3) 0.0369(4) Uani 1 1 d . . . O6 O 0.4317(3) 0.62229(6) 0.0986(2) 0.0288(4) Uani 1 1 d . . . N1 N 0.2382(3) 0.79078(7) 0.4542(3) 0.0229(4) Uani 1 1 d . . . N2 N 0.1860(3) 0.68803(7) 0.0288(3) 0.0234(4) Uani 1 1 d . . . C1 C 0.4413(3) 0.71402(8) 0.4113(3) 0.0225(4) Uani 1 1 d . . . H1A H 0.5949 0.6972 0.4756 0.026(6) Uiso 1 1 calc R . . C2 C 0.4600(3) 0.76399(9) 0.5341(3) 0.0240(4) Uani 1 1 d . . . H2A H 0.4981 0.7551 0.6889 0.018(5) Uiso 1 1 calc R . . C3 C 0.0288(3) 0.76086(8) 0.3343(3) 0.0219(4) Uani 1 1 d . . . H3A H -0.0999 0.7787 0.3572 0.024(6) Uiso 1 1 calc R . . C4 C 0.0517(3) 0.70763(9) 0.4399(3) 0.0236(4) Uani 1 1 d . . . H4A H -0.0789 0.6860 0.3501 0.022(6) Uiso 1 1 calc R . . H4B H 0.0422 0.7117 0.5827 0.025(6) Uiso 1 1 calc R . . C5 C 0.2762(3) 0.67959(9) 0.4695(3) 0.0264(5) Uani 1 1 d . . . H5A H 0.3517 0.6683 0.6214 0.032(7) Uiso 1 1 calc R . . H5B H 0.2406 0.6485 0.3773 0.027(6) Uiso 1 1 calc R . . C6 C -0.0345(3) 0.76002(9) 0.0831(3) 0.0237(4) Uani 1 1 d . . . H6A H -0.1959 0.7725 0.0143 0.022(6) Uiso 1 1 calc R . . C7 C -0.0313(3) 0.70629(9) -0.0045(3) 0.0240(4) Uani 1 1 d . . . C8 C 0.3869(3) 0.71995(8) 0.1626(3) 0.0207(4) Uani 1 1 d . . . H8A H 0.5216 0.7052 0.1398 0.013(5) Uiso 1 1 calc R . . C9 C 0.3514(4) 0.77397(8) 0.0626(3) 0.0237(4) Uani 1 1 d . . . H9A H 0.3818 0.7727 -0.0713 0.019(6) Uiso 1 1 calc R . . H9B H 0.4651 0.7975 0.1639 0.012(5) Uiso 1 1 calc R . . C10 C 0.1108(4) 0.79632(9) 0.0087(3) 0.0258(4) Uani 1 1 d . . . H10A H 0.1234 0.8301 0.0806 0.019(5) Uiso 1 1 calc R . . H10B H 0.0351 0.8018 -0.1488 0.018(6) Uiso 1 1 calc R . . C11 C 0.2296(4) 0.83982(9) 0.5177(3) 0.0263(5) Uani 1 1 d . . . C12 C -0.0309(5) 0.91416(9) 0.4471(5) 0.0364(6) Uani 1 1 d . . . C13 C -0.2816(5) 0.91832(11) 0.2987(6) 0.0506(7) Uani 1 1 d . . . H13A H -0.2997 0.9095 0.1512 0.061(11) Uiso 1 1 calc R . . H13B H -0.3348 0.9536 0.3020 0.074(12) Uiso 1 1 calc R . . H13C H -0.3720 0.8945 0.3472 0.049(9) Uiso 1 1 calc R . . C14 C 0.0045(6) 0.92416(11) 0.6813(5) 0.0489(7) Uani 1 1 d . . . H14A H -0.0852 0.8994 0.7262 0.065(10) Uiso 1 1 calc R . . H14B H -0.0457 0.9592 0.6953 0.077(12) Uiso 1 1 calc R . . H14C H 0.1671 0.9204 0.7730 0.13(2) Uiso 1 1 calc R . . C15 C 0.1160(5) 0.94880(11) 0.3707(5) 0.0434(6) Uani 1 1 d . . . H15A H 0.1052 0.9376 0.2279 0.045(8) Uiso 1 1 calc R . . H15B H 0.2756 0.9468 0.4727 0.066(11) Uiso 1 1 calc R . . H15C H 0.0620 0.9844 0.3624 0.057(10) Uiso 1 1 calc R . . C16 C 0.2194(4) 0.63705(9) -0.0260(3) 0.0257(5) Uani 1 1 d . . . C17 C 0.5164(4) 0.57016(9) 0.0778(4) 0.0330(5) Uani 1 1 d . . . C18 C 0.7614(4) 0.57259(10) 0.2414(5) 0.0430(6) Uani 1 1 d . . . H18A H 0.7617 0.5808 0.3838 0.058(10) Uiso 1 1 calc R . . H18B H 0.8449 0.5993 0.1987 0.050(9) Uiso 1 1 calc R . . H18C H 0.8358 0.5393 0.2472 0.086(14) Uiso 1 1 calc R . . C19 C 0.5112(5) 0.56203(10) -0.1470(5) 0.0393(6) Uani 1 1 d . . . H19A H 0.5923 0.5903 -0.1836 0.043(8) Uiso 1 1 calc R . . H19B H 0.3521 0.5612 -0.2506 0.045(8) Uiso 1 1 calc R . . H19C H 0.5860 0.5294 -0.1525 0.075(12) Uiso 1 1 calc R . . C20 C 0.3780(5) 0.53050(10) 0.1426(5) 0.0424(6) Uani 1 1 d . . . H20A H 0.3775 0.5395 0.2840 0.053(9) Uiso 1 1 calc R . . H20B H 0.4468 0.4964 0.1500 0.066(11) Uiso 1 1 calc R . . H20C H 0.2205 0.5300 0.0354 0.043(8) 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 0.0186(7) 0.0382(8) 0.0343(8) -0.0054(7) 0.0083(6) -0.0040(6) O2 0.0201(7) 0.0365(8) 0.0333(8) 0.0018(7) 0.0039(6) -0.0044(6) O3 0.0259(8) 0.0375(9) 0.0323(8) -0.0087(7) 0.0046(7) -0.0065(7) O4 0.0241(8) 0.0262(8) 0.0401(9) -0.0032(7) 0.0091(7) 0.0036(6) O5 0.0296(9) 0.0374(9) 0.0366(9) -0.0082(7) 0.0049(7) -0.0040(7) O6 0.0267(8) 0.0264(8) 0.0297(8) -0.0030(6) 0.0068(6) 0.0033(6) N1 0.0153(8) 0.0301(9) 0.0218(8) -0.0001(7) 0.0056(7) -0.0003(7) N2 0.0192(8) 0.0292(9) 0.0195(8) -0.0005(7) 0.0051(7) 0.0016(7) C1 0.0170(9) 0.0320(11) 0.0165(9) 0.0029(8) 0.0043(7) 0.0030(8) C2 0.0152(9) 0.0378(12) 0.0174(9) -0.0025(8) 0.0045(7) 0.0014(8) C3 0.0157(9) 0.0295(10) 0.0191(10) -0.0009(8) 0.0051(7) -0.0005(8) C4 0.0190(9) 0.0313(10) 0.0202(9) 0.0023(9) 0.0072(7) 0.0007(8) C5 0.0216(10) 0.0333(11) 0.0238(10) 0.0068(9) 0.0082(8) 0.0030(8) C6 0.0135(9) 0.0325(11) 0.0217(10) 0.0025(8) 0.0030(7) 0.0040(8) C7 0.0185(10) 0.0338(10) 0.0163(8) 0.0007(8) 0.0029(7) -0.0005(8) C8 0.0166(9) 0.0274(10) 0.0179(10) -0.0020(8) 0.0064(7) -0.0008(8) C9 0.0232(10) 0.0278(10) 0.0193(9) 0.0024(8) 0.0072(8) -0.0005(8) C10 0.0264(10) 0.0291(10) 0.0209(10) 0.0047(8) 0.0080(8) 0.0027(8) C11 0.0215(11) 0.0334(12) 0.0238(10) 0.0014(9) 0.0084(9) -0.0010(8) C12 0.0402(13) 0.0225(11) 0.0518(15) 0.0002(10) 0.0237(12) 0.0037(9) C13 0.0384(15) 0.0331(13) 0.082(2) 0.0133(14) 0.0248(14) 0.0125(11) C14 0.0646(19) 0.0339(14) 0.0627(19) -0.0061(13) 0.0405(16) -0.0010(12) C15 0.0467(15) 0.0346(13) 0.0543(15) 0.0029(12) 0.0254(13) -0.0025(11) C16 0.0230(10) 0.0306(11) 0.0215(10) -0.0016(9) 0.0063(8) -0.0011(8) C17 0.0309(12) 0.0259(11) 0.0412(13) -0.0019(10) 0.0127(10) 0.0019(9) C18 0.0330(13) 0.0311(12) 0.0558(16) 0.0009(11) 0.0070(12) 0.0084(10) C19 0.0434(14) 0.0312(12) 0.0491(15) -0.0069(11) 0.0242(12) -0.0013(11) C20 0.0441(15) 0.0356(14) 0.0473(15) 0.0032(11) 0.0172(12) -0.0037(11) _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 C2 1.402(3) . yes O2 C7 1.221(3) . yes O3 C11 1.227(3) . yes O4 C11 1.348(3) . yes O4 C12 1.473(3) . yes O5 C16 1.201(3) . yes O6 C16 1.338(3) . yes O6 C17 1.484(3) . yes N1 C11 1.352(3) . yes N1 C2 1.471(3) . yes N1 C3 1.480(3) . yes N2 C7 1.390(3) . yes N2 C16 1.413(3) . yes N2 C8 1.495(3) . yes C1 C2 1.519(3) . yes C1 C5 1.537(3) . yes C1 C8 1.579(3) . yes C3 C4 1.537(3) . yes C3 C6 1.578(3) . yes C4 C5 1.541(3) . yes C6 C7 1.519(3) . yes C6 C10 1.530(3) . yes C8 C9 1.536(3) . yes C9 C10 1.538(3) . yes C12 C15 1.519(4) . yes C12 C13 1.519(4) . yes C12 C14 1.525(4) . yes C17 C19 1.514(4) . yes C17 C18 1.519(3) . yes C17 C20 1.521(3) . yes O1 H1B 0.86(3) . yes C1 H1A 1.0000 . no C2 H2A 1.0000 . no C3 H3A 1.0000 . no C4 H4A 0.9900 . no C4 H4B 0.9900 . no C5 H5A 0.9900 . no C5 H5B 0.9900 . no C6 H6A 1.0000 . no C8 H8A 1.0000 . no C9 H9A 0.9900 . no C9 H9B 0.9900 . no C10 H10A 0.9900 . no C10 H10B 0.9900 . no C13 H13A 0.9800 . no C13 H13B 0.9800 . no C13 H13C 0.9800 . no C14 H14A 0.9800 . no C14 H14B 0.9800 . no C14 H14C 0.9800 . no C15 H15A 0.9800 . no C15 H15B 0.9800 . no C15 H15C 0.9800 . no C18 H18A 0.9800 . no C18 H18B 0.9800 . no C18 H18C 0.9800 . no C19 H19A 0.9800 . no C19 H19B 0.9800 . no C19 H19C 0.9800 . no C20 H20A 0.9800 . no C20 H20B 0.9800 . no C20 H20C 0.9800 . no 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 C11 O4 C12 121.77(18) . . yes C16 O6 C17 121.03(17) . . yes C11 N1 C2 118.69(18) . . yes C11 N1 C3 122.07(17) . . yes C2 N1 C3 118.62(18) . . yes C7 N2 C16 121.10(18) . . yes C7 N2 C8 117.89(17) . . yes C16 N2 C8 119.96(16) . . yes C2 C1 C5 106.15(16) . . yes C2 C1 C8 115.55(17) . . yes C5 C1 C8 115.69(17) . . yes O1 C2 N1 112.73(19) . . yes O1 C2 C1 110.79(16) . . yes N1 C2 C1 110.05(16) . . yes N1 C3 C4 108.46(16) . . yes N1 C3 C6 113.28(16) . . yes C4 C3 C6 114.93(17) . . yes C3 C4 C5 113.83(17) . . yes C1 C5 C4 112.07(18) . . yes C7 C6 C10 109.95(18) . . yes C7 C6 C3 113.07(17) . . yes C10 C6 C3 113.81(17) . . yes O2 C7 N2 124.1(2) . . yes O2 C7 C6 121.53(19) . . yes N2 C7 C6 114.31(18) . . yes N2 C8 C9 107.29(16) . . yes N2 C8 C1 111.79(16) . . yes C9 C8 C1 119.23(16) . . yes C8 C9 C10 114.39(17) . . yes C6 C10 C9 110.84(18) . . yes O3 C11 O4 125.4(2) . . yes O3 C11 N1 123.3(2) . . yes O4 C11 N1 111.30(18) . . yes O4 C12 C15 110.1(2) . . yes O4 C12 C13 101.8(2) . . yes C15 C12 C13 110.9(2) . . yes O4 C12 C14 109.6(2) . . yes C15 C12 C14 112.5(2) . . yes C13 C12 C14 111.5(2) . . yes O5 C16 O6 126.9(2) . . yes O5 C16 N2 124.4(2) . . yes O6 C16 N2 108.73(17) . . yes O6 C17 C19 110.60(19) . . yes O6 C17 C18 101.49(18) . . yes C19 C17 C18 110.6(2) . . yes O6 C17 C20 108.9(2) . . yes C19 C17 C20 113.4(2) . . yes C18 C17 C20 111.2(2) . . yes C2 O1 H1B 101.7(17) . . yes C2 C1 H1A 106.2 . . no C5 C1 H1A 106.2 . . no C8 C1 H1A 106.2 . . no O1 C2 H2A 107.7 . . no N1 C2 H2A 107.7 . . no C1 C2 H2A 107.7 . . no N1 C3 H3A 106.5 . . no C4 C3 H3A 106.5 . . no C6 C3 H3A 106.5 . . no C3 C4 H4A 108.8 . . no C5 C4 H4A 108.8 . . no C3 C4 H4B 108.8 . . no C5 C4 H4B 108.8 . . no H4A C4 H4B 107.7 . . no C1 C5 H5A 109.2 . . no C4 C5 H5A 109.2 . . no C1 C5 H5B 109.2 . . no C4 C5 H5B 109.2 . . no H5A C5 H5B 107.9 . . no C7 C6 H6A 106.5 . . no C10 C6 H6A 106.5 . . no C3 C6 H6A 106.5 . . no N2 C8 H8A 105.9 . . no C9 C8 H8A 105.9 . . no C1 C8 H8A 105.9 . . no C8 C9 H9A 108.7 . . no C10 C9 H9A 108.7 . . no C8 C9 H9B 108.7 . . no C10 C9 H9B 108.7 . . no H9A C9 H9B 107.6 . . no C6 C10 H10A 109.5 . . no C9 C10 H10A 109.5 . . no C6 C10 H10B 109.5 . . no C9 C10 H10B 109.5 . . no H10A C10 H10B 108.1 . . no C12 C13 H13A 109.5 . . no C12 C13 H13B 109.5 . . no H13A C13 H13B 109.5 . . no C12 C13 H13C 109.5 . . no H13A C13 H13C 109.5 . . no H13B C13 H13C 109.5 . . no C12 C14 H14A 109.5 . . no C12 C14 H14B 109.5 . . no H14A C14 H14B 109.5 . . no C12 C14 H14C 109.5 . . no H14A C14 H14C 109.5 . . no H14B C14 H14C 109.5 . . no C12 C15 H15A 109.5 . . no C12 C15 H15B 109.5 . . no H15A C15 H15B 109.5 . . no C12 C15 H15C 109.5 . . no H15A C15 H15C 109.5 . . no H15B C15 H15C 109.5 . . no C17 C18 H18A 109.5 . . no C17 C18 H18B 109.5 . . no H18A C18 H18B 109.5 . . no C17 C18 H18C 109.5 . . no H18A C18 H18C 109.5 . . no H18B C18 H18C 109.5 . . no C17 C19 H19A 109.5 . . no C17 C19 H19B 109.5 . . no H19A C19 H19B 109.5 . . no C17 C19 H19C 109.5 . . no H19A C19 H19C 109.5 . . no H19B C19 H19C 109.5 . . no C17 C20 H20A 109.5 . . no C17 C20 H20B 109.5 . . no H20A C20 H20B 109.5 . . no C17 C20 H20C 109.5 . . no H20A C20 H20C 109.5 . . no H20B C20 H20C 109.5 . . no 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 C11 N1 C2 O1 -44.8(2) . . . . no C3 N1 C2 O1 144.08(17) . . . . no C11 N1 C2 C1 -169.01(17) . . . . no C3 N1 C2 C1 19.8(2) . . . . no C5 C1 C2 O1 169.11(16) . . . . no C8 C1 C2 O1 -61.2(2) . . . . no C5 C1 C2 N1 -65.5(2) . . . . no C8 C1 C2 N1 64.2(2) . . . . no C11 N1 C3 C4 -132.56(19) . . . . no C2 N1 C3 C4 38.3(2) . . . . no C11 N1 C3 C6 98.6(2) . . . . no C2 N1 C3 C6 -90.6(2) . . . . no N1 C3 C4 C5 -51.7(2) . . . . no C6 C3 C4 C5 76.3(2) . . . . no C2 C1 C5 C4 50.7(2) . . . . no C8 C1 C5 C4 -78.9(2) . . . . no C3 C4 C5 C1 6.9(2) . . . . no N1 C3 C6 C7 118.01(19) . . . . no C4 C3 C6 C7 -7.5(2) . . . . no N1 C3 C6 C10 -8.4(2) . . . . no C4 C3 C6 C10 -133.85(18) . . . . no C16 N2 C7 O2 -3.7(3) . . . . no C8 N2 C7 O2 -171.94(19) . . . . no C16 N2 C7 C6 174.29(18) . . . . no C8 N2 C7 C6 6.0(2) . . . . no C10 C6 C7 O2 -132.7(2) . . . . no C3 C6 C7 O2 98.8(2) . . . . no C10 C6 C7 N2 49.2(2) . . . . no C3 C6 C7 N2 -79.2(2) . . . . no C7 N2 C8 C9 -54.4(2) . . . . no C16 N2 C8 C9 137.16(18) . . . . no C7 N2 C8 C1 78.0(2) . . . . no C16 N2 C8 C1 -90.4(2) . . . . no C2 C1 C8 N2 -127.64(18) . . . . no C5 C1 C8 N2 -2.8(2) . . . . no C2 C1 C8 C9 -1.4(2) . . . . no C5 C1 C8 C9 123.4(2) . . . . no N2 C8 C9 C10 47.2(2) . . . . no C1 C8 C9 C10 -81.1(2) . . . . no C7 C6 C10 C9 -52.3(2) . . . . no C3 C6 C10 C9 75.7(2) . . . . no C8 C9 C10 C6 3.8(2) . . . . no C12 O4 C11 O3 5.0(3) . . . . no C12 O4 C11 N1 -174.24(19) . . . . no C2 N1 C11 O3 -3.1(3) . . . . no C3 N1 C11 O3 167.8(2) . . . . no C2 N1 C11 O4 176.24(17) . . . . no C3 N1 C11 O4 -12.9(3) . . . . no C11 O4 C12 C15 58.9(3) . . . . no C11 O4 C12 C13 176.6(2) . . . . no C11 O4 C12 C14 -65.3(3) . . . . no C17 O6 C16 O5 0.5(3) . . . . no C17 O6 C16 N2 179.94(18) . . . . no C7 N2 C16 O5 25.7(3) . . . . no C8 N2 C16 O5 -166.3(2) . . . . no C7 N2 C16 O6 -153.75(18) . . . . no C8 N2 C16 O6 14.3(3) . . . . no C16 O6 C17 C19 60.4(3) . . . . no C16 O6 C17 C18 177.8(2) . . . . no C16 O6 C17 C20 -64.9(3) . . . . 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 O1 H1B O3 0.86(3) 1.98(3) 2.668(3) 136(2) . _diffrn_measured_fraction_theta_max 0.983 _diffrn_reflns_theta_full 67.45 _diffrn_measured_fraction_theta_full 0.983 _refine_diff_density_max 0.193 _refine_diff_density_min -0.216 _refine_diff_density_rms 0.049