# Electronic Supplementary Material (ESI) for CrystEngComm # This journal is © The Royal Society of Chemistry 2013 ####################################################################### # # Cambridge Crystallographic Data Centre # CCDC # ####################################################################### # # This CIF contains data from an original supplementary publication # deposited with the CCDC, and may include chemical, crystal, # experimental, refinement, atomic coordinates, # anisotropic displacement parameters and molecular geometry data, # as required by the journal to which it was submitted. # # This CIF is provided on the understanding that it is used for bona # fide research purposes only. It may contain copyright material # of the CCDC or of third parties, and may not be copied or further # disseminated in any form, whether machine-readable or not, # except for the purpose of generating routine backup copies # on your local computer system. # # For further information on the CCDC, data deposition and # data retrieval see: # www.ccdc.cam.ac.uk # # Bona fide researchers may freely download Mercury and enCIFer # from this site to visualise CIF-encoded structures and # to carry out CIF format checking respectively. # data_H2.CIF _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common 'Hup A Form H2' _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C15 H20 N2 O2' _chemical_formula_weight 256.33 _chemical_absolute_configuration unk 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 orthorhombic _symmetry_space_group_name_H-M P21212 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, z' 'x+1/2, -y+1/2, -z' '-x+1/2, y+1/2, -z' _cell_length_a 12.0653(5) _cell_length_b 29.4244(12) _cell_length_c 7.6893(3) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 2729.81(19) _cell_formula_units_Z 8 _cell_measurement_temperature 296(2) _cell_measurement_reflns_used 6169 _cell_measurement_theta_min 4.50 _cell_measurement_theta_max 54.87 _exptl_crystal_description block _exptl_crystal_colour colorless _exptl_crystal_size_max 0.25 _exptl_crystal_size_mid 0.22 _exptl_crystal_size_min 0.20 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.247 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1104 _exptl_absorpt_coefficient_mu 0.082 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.6526 _exptl_absorpt_correction_T_max 0.7456 _exptl_absorpt_process_details sadabs _exptl_special_details ; ? ; _diffrn_ambient_temperature 296(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 'Bruker APEX-II CCD' _diffrn_measurement_method '\f and \w scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 14162 _diffrn_reflns_av_R_equivalents 0.0835 _diffrn_reflns_av_sigmaI/netI 0.1487 _diffrn_reflns_limit_h_min -15 _diffrn_reflns_limit_h_max 11 _diffrn_reflns_limit_k_min -30 _diffrn_reflns_limit_k_max 38 _diffrn_reflns_limit_l_min -5 _diffrn_reflns_limit_l_max 9 _diffrn_reflns_theta_min 1.82 _diffrn_reflns_theta_max 27.50 _reflns_number_total 6019 _reflns_number_gt 3340 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker APEX2' _computing_cell_refinement 'Bruker SAINT' _computing_data_reduction 'Bruker SAINT' _computing_structure_solution 'SHELXS-97 (Sheldrick, 2008)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 2008)' _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^)+(0.0201P)^2^+0.0000P] 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 0.0043(5) _refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^ _refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881' _refine_ls_abs_structure_Flack -0.9(14) _refine_ls_number_reflns 6019 _refine_ls_number_parameters 353 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.1092 _refine_ls_R_factor_gt 0.0497 _refine_ls_wR_factor_ref 0.0912 _refine_ls_wR_factor_gt 0.0793 _refine_ls_goodness_of_fit_ref 0.827 _refine_ls_restrained_S_all 0.827 _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 0.72963(16) 1.11263(7) -0.1532(2) 0.0224(5) Uani 1 1 d . A 4 O1S O 0.0005(7) 0.4761(3) 0.4610(8) 0.063(3) Uiso 0.387(6) 1 d P . 1 O1' O 0.71860(16) 0.09783(6) 0.3473(2) 0.0205(5) Uani 1 1 d . . . N1 N 0.75579(17) 1.05266(8) 0.0304(2) 0.0164(5) Uani 1 1 d . A . H37 H 0.7365 1.0697 0.1161 0.020 Uiso 1 1 calc R . . N2 N 0.94824(18) 0.92115(9) -0.1457(3) 0.0259(6) Uani 1 1 d . . . H2A H 1.0029 0.9407 -0.1253 0.039 Uiso 1 1 d R . . H2C H 0.9722 0.8930 -0.1267 0.039 Uiso 1 1 d R . . N1' N 0.69350(17) 0.15783(8) 0.5306(2) 0.0156(5) Uani 1 1 d . . . H3 H 0.7124 0.1408 0.6165 0.019 Uiso 1 1 calc R . . N2' N 0.50122(18) 0.28825(8) 0.3496(2) 0.0213(6) Uani 1 1 d . . . H4B H 0.4792 0.3169 0.3631 0.032 Uiso 1 1 d R . . H4C H 0.4448 0.2696 0.3715 0.032 Uiso 1 1 d R . . C15 C 1.0053(2) 0.91217(12) 0.4233(3) 0.0294(8) Uani 1 1 d . . . H12 H 1.0349 0.9409 0.4605 0.044 Uiso 1 1 calc R . . H36 H 1.0597 0.8888 0.4411 0.044 Uiso 1 1 calc R . . H13 H 0.9400 0.9053 0.4895 0.044 Uiso 1 1 calc R . . C14 C 0.9761(2) 0.91467(10) 0.2328(3) 0.0217(7) Uani 1 1 d . . . H11 H 1.0314 0.9067 0.1542 0.026 Uiso 1 1 calc R . . C12 C 0.8801(2) 0.92709(10) 0.1668(3) 0.0167(6) Uani 1 1 d . . . C6 C 0.8552(2) 0.93107(10) -0.0264(3) 0.0176(7) Uani 1 1 d . . . C4 C 0.8179(2) 0.98004(9) -0.0628(3) 0.0144(6) Uani 1 1 d . A . C5 C 0.7859(2) 1.00908(10) 0.0675(3) 0.0155(6) Uani 1 1 d . . . C1 C 0.7539(2) 1.07160(10) -0.1334(3) 0.0173(7) Uani 1 1 d . . . C10 C 0.7810(2) 0.94286(9) 0.2707(3) 0.0172(7) Uani 1 1 d . . . H10 H 0.7912 0.9343 0.3929 0.021 Uiso 1 1 calc R . . C11 C 0.7777(2) 0.99504(9) 0.2562(3) 0.0175(6) Uani 1 1 d . . . H2 H 0.7091 1.0064 0.3055 0.021 Uiso 1 1 calc R . . H35 H 0.8388 1.0081 0.3211 0.021 Uiso 1 1 calc R . . C9 C 0.6748(2) 0.92199(10) 0.2037(3) 0.0208(7) Uani 1 1 d . . . H9 H 0.6121 0.9239 0.2738 0.025 Uiso 1 1 calc R . . C8 C 0.6650(2) 0.90114(10) 0.0518(3) 0.0222(7) Uani 1 1 d . . . C7 C 0.7622(2) 0.89774(10) -0.0709(3) 0.0221(7) Uani 1 1 d . . . H5 H 0.7368 0.9036 -0.1885 0.026 Uiso 1 1 calc R . . H4 H 0.7913 0.8670 -0.0674 0.026 Uiso 1 1 calc R . . C13 C 0.5590(3) 0.87896(12) -0.0066(4) 0.0366(9) Uani 1 1 d . . . H7 H 0.5025 0.8839 0.0793 0.055 Uiso 1 1 calc R . . H8 H 0.5709 0.8469 -0.0209 0.055 Uiso 1 1 calc R . . H6 H 0.5360 0.8919 -0.1153 0.055 Uiso 1 1 calc R . . C3 C 0.8129(2) 0.99764(10) -0.2357(3) 0.0194(7) Uani 1 1 d . . . H15 H 0.8318 0.9787 -0.3278 0.023 Uiso 1 1 calc R A . C2 C 0.7818(2) 1.04058(10) -0.2704(3) 0.0174(7) Uani 1 1 d . A . H14 H 0.7782 1.0503 -0.3853 0.021 Uiso 1 1 calc R . . C13' C 0.8847(2) 0.33400(11) 0.5045(3) 0.0219(7) Uani 1 1 d . . . H18 H 0.9363 0.3344 0.5996 0.033 Uiso 1 1 calc R . . H31 H 0.8684 0.3646 0.4696 0.033 Uiso 1 1 calc R . . H32 H 0.9166 0.3178 0.4084 0.033 Uiso 1 1 calc R . . C8' C 0.7796(2) 0.31073(10) 0.5607(3) 0.0187(7) Uani 1 1 d . . . C7' C 0.6862(2) 0.31229(9) 0.4311(3) 0.0175(6) Uani 1 1 d . . . H29 H 0.7155 0.3056 0.3164 0.021 Uiso 1 1 calc R . . H30 H 0.6560 0.3428 0.4284 0.021 Uiso 1 1 calc R . . C6' C 0.5921(2) 0.27859(10) 0.4721(3) 0.0165(7) Uani 1 1 d . . . C4' C 0.6317(2) 0.23036(10) 0.4376(3) 0.0150(6) Uani 1 1 d . . . C5' C 0.6643(2) 0.20133(10) 0.5673(3) 0.0152(6) Uani 1 1 d . . . C1' C 0.6954(2) 0.13867(10) 0.3665(3) 0.0180(7) Uani 1 1 d . . . C3' C 0.6376(2) 0.21311(10) 0.2649(3) 0.0161(6) Uani 1 1 d . . . H20 H 0.6196 0.2323 0.1730 0.019 Uiso 1 1 calc R . . C2' C 0.6683(2) 0.16988(10) 0.2294(3) 0.0171(6) Uani 1 1 d . . . H19 H 0.6719 0.1602 0.1143 0.021 Uiso 1 1 calc R . . C12' C 0.5622(2) 0.28234(10) 0.6648(3) 0.0150(6) Uani 1 1 d . . . C14' C 0.4647(2) 0.29336(10) 0.7255(3) 0.0228(7) Uani 1 1 d . . . H24 H 0.4111 0.3007 0.6433 0.027 Uiso 1 1 calc R . . C15' C 0.4288(2) 0.29564(12) 0.9137(3) 0.0320(9) Uani 1 1 d . . . H23 H 0.4920 0.2912 0.9877 0.048 Uiso 1 1 calc R . . H21 H 0.3751 0.2723 0.9361 0.048 Uiso 1 1 calc R . . H22 H 0.3965 0.3248 0.9369 0.048 Uiso 1 1 calc R . . C10' C 0.6614(2) 0.26750(10) 0.7725(3) 0.0166(6) Uani 1 1 d . . . H25 H 0.6477 0.2755 0.8943 0.020 Uiso 1 1 calc R . . C11' C 0.6694(2) 0.21517(9) 0.7583(3) 0.0162(6) Uani 1 1 d . . . H26 H 0.7384 0.2048 0.8092 0.019 Uiso 1 1 calc R . . H27 H 0.6087 0.2012 0.8215 0.019 Uiso 1 1 calc R . . C9' C 0.7670(2) 0.29071(10) 0.7139(3) 0.0197(7) Uani 1 1 d . . . H28 H 0.8268 0.2909 0.7902 0.024 Uiso 1 1 calc R . . O2S O 0.0000 0.5000 0.1304(5) 0.1005(16) Uani 1 2 d S . . O2' O -0.0714(4) 0.45351(18) 0.3766(5) 0.0669(19) Uani 0.635(7) 1 d P B 1 O2'' O -0.0293(5) 0.4878(2) 0.3264(8) 0.037(3) Uiso 0.365(7) 1 d P . 2 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 0.0364(13) 0.0147(12) 0.0160(10) 0.0027(9) -0.0014(9) 0.0023(11) O1' 0.0340(13) 0.0127(12) 0.0149(9) -0.0018(9) -0.0042(9) 0.0031(10) N1 0.0219(14) 0.0151(14) 0.0123(11) -0.0004(10) -0.0013(9) 0.0010(12) N2 0.0282(15) 0.0247(16) 0.0247(12) 0.0006(12) 0.0062(11) 0.0092(13) N1' 0.0207(14) 0.0143(13) 0.0118(12) 0.0023(10) -0.0038(10) 0.0027(12) N2' 0.0250(15) 0.0232(15) 0.0157(11) 0.0009(12) -0.0058(11) 0.0078(12) C15 0.0273(18) 0.035(2) 0.0256(16) 0.0077(16) -0.0074(13) -0.0060(16) C14 0.0248(18) 0.0204(18) 0.0200(15) 0.0026(14) 0.0059(13) -0.0048(15) C12 0.0200(16) 0.0100(15) 0.0202(14) -0.0006(13) 0.0005(13) -0.0039(13) C6 0.0226(18) 0.0158(16) 0.0144(14) -0.0006(13) 0.0026(11) 0.0027(14) C4 0.0147(16) 0.0121(15) 0.0165(14) 0.0010(13) 0.0021(12) -0.0005(13) C5 0.0168(16) 0.0150(17) 0.0147(13) 0.0023(13) -0.0032(12) -0.0066(13) C1 0.0171(17) 0.0177(18) 0.0170(14) 0.0000(13) -0.0027(12) -0.0031(14) C10 0.0265(17) 0.0181(16) 0.0070(12) 0.0029(13) 0.0019(11) 0.0003(14) C11 0.0234(16) 0.0175(16) 0.0116(13) 0.0000(13) 0.0036(12) -0.0023(14) C9 0.0212(17) 0.0194(17) 0.0216(16) 0.0067(14) 0.0033(12) -0.0012(14) C8 0.0274(18) 0.0166(17) 0.0226(15) 0.0078(14) -0.0037(13) -0.0037(15) C7 0.036(2) 0.0124(16) 0.0178(14) 0.0001(13) -0.0035(13) 0.0020(15) C13 0.037(2) 0.036(2) 0.0366(19) 0.0080(17) -0.0124(15) -0.0142(19) C3 0.0230(17) 0.0202(17) 0.0148(14) -0.0047(14) 0.0030(13) -0.0023(14) C2 0.0231(16) 0.0206(17) 0.0084(13) 0.0042(13) 0.0045(12) 0.0010(14) C13' 0.0246(18) 0.0186(17) 0.0225(15) -0.0015(14) -0.0001(12) -0.0009(15) C8' 0.0222(17) 0.0121(16) 0.0218(15) -0.0025(14) 0.0008(13) 0.0030(14) C7' 0.0209(17) 0.0135(16) 0.0180(13) 0.0017(13) 0.0027(12) 0.0044(13) C6' 0.0207(17) 0.0173(16) 0.0114(13) 0.0018(13) -0.0042(11) 0.0008(14) C4' 0.0187(16) 0.0128(16) 0.0135(14) -0.0017(13) -0.0027(12) 0.0005(13) C5' 0.0159(16) 0.0121(16) 0.0177(14) -0.0014(13) 0.0013(12) -0.0016(13) C1' 0.0183(18) 0.0189(18) 0.0167(15) -0.0022(13) -0.0017(12) -0.0016(14) C3' 0.0161(16) 0.0176(17) 0.0147(14) 0.0028(14) -0.0029(12) -0.0007(13) C2' 0.0197(16) 0.0213(17) 0.0104(13) 0.0004(14) -0.0020(11) -0.0037(14) C12' 0.0193(16) 0.0125(17) 0.0132(13) 0.0002(13) -0.0023(12) 0.0010(13) C14' 0.0218(17) 0.0285(19) 0.0181(14) 0.0048(14) 0.0001(13) 0.0075(15) C15' 0.031(2) 0.049(2) 0.0152(15) 0.0042(16) 0.0033(13) 0.0095(18) C10' 0.0241(16) 0.0161(16) 0.0094(13) -0.0006(13) -0.0020(12) 0.0042(14) C11' 0.0226(16) 0.0161(16) 0.0098(14) -0.0001(13) -0.0033(12) -0.0017(14) C9' 0.0244(17) 0.0167(16) 0.0180(14) -0.0057(13) -0.0069(12) 0.0028(14) O2S 0.138(4) 0.089(4) 0.074(3) 0.000 0.000 0.013(3) O2' 0.084(4) 0.056(4) 0.061(3) 0.016(3) 0.000(2) -0.011(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 C1 1.252(3) . ? O1S O2' 1.271(8) . ? O1S O1S 1.409(16) 2_565 ? O1' C1' 1.243(3) . ? N1 C5 1.363(3) . ? N1 C1 1.378(3) . ? N1 H37 0.8600 . ? N2 C6 1.479(3) . ? N2 H2A 0.8900 . ? N2 H2C 0.8900 . ? N1' C5' 1.357(3) . ? N1' C1' 1.382(3) . ? N1' H3 0.8600 . ? N2' C6' 1.473(3) . ? N2' H4B 0.8900 . ? N2' H4C 0.8900 . ? C15 C14 1.509(4) . ? C15 H12 0.9600 . ? C15 H36 0.9600 . ? C15 H13 0.9600 . ? C14 C12 1.316(4) . ? C14 H11 0.9300 . ? C12 C10 1.511(4) . ? C12 C6 1.521(3) . ? C6 C7 1.529(4) . ? C6 C4 1.535(4) . ? C4 C5 1.372(4) . ? C4 C3 1.428(3) . ? C5 C11 1.512(3) . ? C1 C2 1.434(4) . ? C10 C9 1.512(4) . ? C10 C11 1.540(4) . ? C10 H10 0.9800 . ? C11 H2 0.9700 . ? C11 H35 0.9700 . ? C9 C8 1.325(3) . ? C9 H9 0.9300 . ? C8 C13 1.504(4) . ? C8 C7 1.508(4) . ? C7 H5 0.9700 . ? C7 H4 0.9700 . ? C13 H7 0.9600 . ? C13 H8 0.9600 . ? C13 H6 0.9600 . ? C3 C2 1.345(4) . ? C3 H15 0.9300 . ? C2 H14 0.9300 . ? C13' C8' 1.506(4) . ? C13' H18 0.9600 . ? C13' H31 0.9600 . ? C13' H32 0.9600 . ? C8' C9' 1.326(3) . ? C8' C7' 1.504(3) . ? C7' C6' 1.540(4) . ? C7' H29 0.9700 . ? C7' H30 0.9700 . ? C6' C4' 1.521(4) . ? C6' C12' 1.529(3) . ? C4' C5' 1.371(3) . ? C4' C3' 1.423(3) . ? C5' C11' 1.525(3) . ? C1' C2' 1.436(4) . ? C3' C2' 1.353(4) . ? C3' H20 0.9300 . ? C2' H19 0.9300 . ? C12' C14' 1.306(4) . ? C12' C10' 1.520(4) . ? C14' C15' 1.512(4) . ? C14' H24 0.9300 . ? C15' H23 0.9600 . ? C15' H21 0.9600 . ? C15' H22 0.9600 . ? C10' C9' 1.514(4) . ? C10' C11' 1.547(4) . ? C10' H25 0.9800 . ? C11' H26 0.9700 . ? C11' H27 0.9700 . ? C9' H28 0.9300 . ? O2S O2'' 1.589(7) . ? O2S O2'' 1.589(7) 2_565 ? O2'' O2'' 1.008(13) 2_565 ? 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 O2' O1S O1S 121.1(7) . 2_565 ? C5 N1 C1 125.2(2) . . ? C5 N1 H37 117.4 . . ? C1 N1 H37 117.4 . . ? C6 N2 H2A 109.0 . . ? C6 N2 H2C 109.2 . . ? H2A N2 H2C 109.5 . . ? C5' N1' C1' 125.3(2) . . ? C5' N1' H3 117.3 . . ? C1' N1' H3 117.3 . . ? C6' N2' H4B 109.3 . . ? C6' N2' H4C 109.2 . . ? H4B N2' H4C 109.5 . . ? C14 C15 H12 109.5 . . ? C14 C15 H36 109.5 . . ? H12 C15 H36 109.5 . . ? C14 C15 H13 109.5 . . ? H12 C15 H13 109.5 . . ? H36 C15 H13 109.5 . . ? C12 C14 C15 126.4(3) . . ? C12 C14 H11 116.8 . . ? C15 C14 H11 116.8 . . ? C14 C12 C10 125.3(2) . . ? C14 C12 C6 124.9(3) . . ? C10 C12 C6 109.6(2) . . ? N2 C6 C12 116.1(2) . . ? N2 C6 C7 107.0(2) . . ? C12 C6 C7 108.3(2) . . ? N2 C6 C4 107.1(2) . . ? C12 C6 C4 107.9(2) . . ? C7 C6 C4 110.3(2) . . ? C5 C4 C3 116.2(3) . . ? C5 C4 C6 122.3(2) . . ? C3 C4 C6 121.5(2) . . ? N1 C5 C4 120.6(2) . . ? N1 C5 C11 116.1(2) . . ? C4 C5 C11 123.3(3) . . ? O1 C1 N1 120.3(2) . . ? O1 C1 C2 125.4(2) . . ? N1 C1 C2 114.2(2) . . ? C12 C10 C9 111.5(2) . . ? C12 C10 C11 106.7(2) . . ? C9 C10 C11 111.0(2) . . ? C12 C10 H10 109.2 . . ? C9 C10 H10 109.2 . . ? C11 C10 H10 109.2 . . ? C5 C11 C10 109.9(2) . . ? C5 C11 H2 109.7 . . ? C10 C11 H2 109.7 . . ? C5 C11 H35 109.7 . . ? C10 C11 H35 109.7 . . ? H2 C11 H35 108.2 . . ? C8 C9 C10 124.3(2) . . ? C8 C9 H9 117.8 . . ? C10 C9 H9 117.8 . . ? C9 C8 C13 122.6(3) . . ? C9 C8 C7 120.9(3) . . ? C13 C8 C7 116.5(3) . . ? C8 C7 C6 112.8(2) . . ? C8 C7 H5 109.0 . . ? C6 C7 H5 109.0 . . ? C8 C7 H4 109.0 . . ? C6 C7 H4 109.0 . . ? H5 C7 H4 107.8 . . ? C8 C13 H7 109.5 . . ? C8 C13 H8 109.5 . . ? H7 C13 H8 109.5 . . ? C8 C13 H6 109.5 . . ? H7 C13 H6 109.5 . . ? H8 C13 H6 109.5 . . ? C2 C3 C4 122.5(3) . . ? C2 C3 H15 118.8 . . ? C4 C3 H15 118.8 . . ? C3 C2 C1 121.2(2) . . ? C3 C2 H14 119.4 . . ? C1 C2 H14 119.4 . . ? C8' C13' H18 109.5 . . ? C8' C13' H31 109.5 . . ? H18 C13' H31 109.5 . . ? C8' C13' H32 109.5 . . ? H18 C13' H32 109.5 . . ? H31 C13' H32 109.5 . . ? C9' C8' C7' 121.1(3) . . ? C9' C8' C13' 123.6(3) . . ? C7' C8' C13' 115.3(2) . . ? C8' C7' C6' 113.4(2) . . ? C8' C7' H29 108.9 . . ? C6' C7' H29 108.9 . . ? C8' C7' H30 108.9 . . ? C6' C7' H30 108.9 . . ? H29 C7' H30 107.7 . . ? N2' C6' C4' 107.6(2) . . ? N2' C6' C12' 115.4(2) . . ? C4' C6' C12' 108.1(2) . . ? N2' C6' C7' 107.1(2) . . ? C4' C6' C7' 109.5(2) . . ? C12' C6' C7' 109.0(2) . . ? C5' C4' C3' 116.3(3) . . ? C5' C4' C6' 123.0(2) . . ? C3' C4' C6' 120.7(2) . . ? N1' C5' C4' 120.7(2) . . ? N1' C5' C11' 116.2(2) . . ? C4' C5' C11' 123.1(2) . . ? O1' C1' N1' 120.4(3) . . ? O1' C1' C2' 125.6(2) . . ? N1' C1' C2' 113.9(3) . . ? C2' C3' C4' 122.5(3) . . ? C2' C3' H20 118.8 . . ? C4' C3' H20 118.8 . . ? C3' C2' C1' 121.0(3) . . ? C3' C2' H19 119.5 . . ? C1' C2' H19 119.5 . . ? C14' C12' C10' 125.9(2) . . ? C14' C12' C6' 125.2(2) . . ? C10' C12' C6' 108.7(2) . . ? C12' C14' C15' 127.7(3) . . ? C12' C14' H24 116.2 . . ? C15' C14' H24 116.2 . . ? C14' C15' H23 109.5 . . ? C14' C15' H21 109.5 . . ? H23 C15' H21 109.5 . . ? C14' C15' H22 109.5 . . ? H23 C15' H22 109.5 . . ? H21 C15' H22 109.5 . . ? C9' C10' C12' 111.8(2) . . ? C9' C10' C11' 112.1(2) . . ? C12' C10' C11' 107.3(2) . . ? C9' C10' H25 108.5 . . ? C12' C10' H25 108.5 . . ? C11' C10' H25 108.5 . . ? C5' C11' C10' 109.3(2) . . ? C5' C11' H26 109.8 . . ? C10' C11' H26 109.8 . . ? C5' C11' H27 109.8 . . ? C10' C11' H27 109.8 . . ? H26 C11' H27 108.3 . . ? C8' C9' C10' 124.1(3) . . ? C8' C9' H28 117.9 . . ? C10' C9' H28 117.9 . . ? O2'' O2S O2'' 37.0(4) . 2_565 ? O2'' O2'' O2S 71.5(2) 2_565 . ? 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 C15 C14 C12 C10 2.1(5) . . . . ? C15 C14 C12 C6 177.4(3) . . . . ? C14 C12 C6 N2 -1.6(4) . . . . ? C10 C12 C6 N2 174.2(2) . . . . ? C14 C12 C6 C7 118.7(3) . . . . ? C10 C12 C6 C7 -65.5(3) . . . . ? C14 C12 C6 C4 -121.9(3) . . . . ? C10 C12 C6 C4 54.0(3) . . . . ? N2 C6 C4 C5 -141.5(3) . . . . ? C12 C6 C4 C5 -15.8(4) . . . . ? C7 C6 C4 C5 102.4(3) . . . . ? N2 C6 C4 C3 39.7(4) . . . . ? C12 C6 C4 C3 165.4(2) . . . . ? C7 C6 C4 C3 -76.4(3) . . . . ? C1 N1 C5 C4 0.2(4) . . . . ? C1 N1 C5 C11 -177.8(2) . . . . ? C3 C4 C5 N1 -2.6(4) . . . . ? C6 C4 C5 N1 178.5(2) . . . . ? C3 C4 C5 C11 175.2(3) . . . . ? C6 C4 C5 C11 -3.7(4) . . . . ? C5 N1 C1 O1 -176.8(3) . . . . ? C5 N1 C1 C2 3.0(4) . . . . ? C14 C12 C10 C9 -136.7(3) . . . . ? C6 C12 C10 C9 47.4(3) . . . . ? C14 C12 C10 C11 101.9(3) . . . . ? C6 C12 C10 C11 -73.9(3) . . . . ? N1 C5 C11 C10 163.7(2) . . . . ? C4 C5 C11 C10 -14.2(4) . . . . ? C12 C10 C11 C5 50.4(3) . . . . ? C9 C10 C11 C5 -71.2(3) . . . . ? C12 C10 C9 C8 -14.3(4) . . . . ? C11 C10 C9 C8 104.5(3) . . . . ? C10 C9 C8 C13 177.1(3) . . . . ? C10 C9 C8 C7 -1.6(4) . . . . ? C9 C8 C7 C6 -16.4(4) . . . . ? C13 C8 C7 C6 164.7(2) . . . . ? N2 C6 C7 C8 174.9(2) . . . . ? C12 C6 C7 C8 49.0(3) . . . . ? C4 C6 C7 C8 -69.0(3) . . . . ? C5 C4 C3 C2 1.9(4) . . . . ? C6 C4 C3 C2 -179.2(3) . . . . ? C4 C3 C2 C1 1.3(4) . . . . ? O1 C1 C2 C3 176.2(3) . . . . ? N1 C1 C2 C3 -3.6(4) . . . . ? C9' C8' C7' C6' -15.6(4) . . . . ? C13' C8' C7' C6' 165.5(2) . . . . ? C8' C7' C6' N2' 172.5(2) . . . . ? C8' C7' C6' C4' -71.1(3) . . . . ? C8' C7' C6' C12' 47.0(3) . . . . ? N2' C6' C4' C5' -142.5(2) . . . . ? C12' C6' C4' C5' -17.2(4) . . . . ? C7' C6' C4' C5' 101.5(3) . . . . ? N2' C6' C4' C3' 38.0(3) . . . . ? C12' C6' C4' C3' 163.4(2) . . . . ? C7' C6' C4' C3' -78.0(3) . . . . ? C1' N1' C5' C4' 0.9(4) . . . . ? C1' N1' C5' C11' -179.5(2) . . . . ? C3' C4' C5' N1' -3.9(4) . . . . ? C6' C4' C5' N1' 176.6(2) . . . . ? C3' C4' C5' C11' 176.5(2) . . . . ? C6' C4' C5' C11' -3.0(4) . . . . ? C5' N1' C1' O1' -176.7(3) . . . . ? C5' N1' C1' C2' 3.0(4) . . . . ? C5' C4' C3' C2' 3.1(4) . . . . ? C6' C4' C3' C2' -177.4(3) . . . . ? C4' C3' C2' C1' 0.9(4) . . . . ? O1' C1' C2' C3' 175.9(3) . . . . ? N1' C1' C2' C3' -3.8(4) . . . . ? N2' C6' C12' C14' -0.3(4) . . . . ? C4' C6' C12' C14' -120.8(3) . . . . ? C7' C6' C12' C14' 120.3(3) . . . . ? N2' C6' C12' C10' 175.2(2) . . . . ? C4' C6' C12' C10' 54.7(3) . . . . ? C7' C6' C12' C10' -64.2(3) . . . . ? C10' C12' C14' C15' 2.4(5) . . . . ? C6' C12' C14' C15' 177.1(3) . . . . ? C14' C12' C10' C9' -135.3(3) . . . . ? C6' C12' C10' C9' 49.3(3) . . . . ? C14' C12' C10' C11' 101.5(3) . . . . ? C6' C12' C10' C11' -73.9(3) . . . . ? N1' C5' C11' C10' 166.5(2) . . . . ? C4' C5' C11' C10' -13.8(4) . . . . ? C9' C10' C11' C5' -72.9(3) . . . . ? C12' C10' C11' C5' 50.1(3) . . . . ? C7' C8' C9' C10' 0.7(4) . . . . ? C13' C8' C9' C10' 179.5(3) . . . . ? C12' C10' C9' C8' -18.3(4) . . . . ? C11' C10' C9' C8' 102.2(3) . . . . ? _diffrn_measured_fraction_theta_max 0.999 _diffrn_reflns_theta_full 27.50 _diffrn_measured_fraction_theta_full 0.999 _refine_diff_density_max 0.705 _refine_diff_density_min -0.359 _refine_diff_density_rms 0.048 _database_code_depnum_ccdc_archive 'CCDC 958406' ####################################################################### # # Cambridge Crystallographic Data Centre # CCDC # ####################################################################### # # This CIF contains data from an original supplementary publication # deposited with the CCDC, and may include chemical, crystal, # experimental, refinement, atomic coordinates, # anisotropic displacement parameters and molecular geometry data, # as required by the journal to which it was submitted. # # This CIF is provided on the understanding that it is used for bona # fide research purposes only. It may contain copyright material # of the CCDC or of third parties, and may not be copied or further # disseminated in any form, whether machine-readable or not, # except for the purpose of generating routine backup copies # on your local computer system. # # For further information on the CCDC, data deposition and # data retrieval see: # www.ccdc.cam.ac.uk # # Bona fide researchers may freely download Mercury and enCIFer # from this site to visualise CIF-encoded structures and # to carry out CIF format checking respectively. # data_S1.CIF _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common 'Hup A Form S1' _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C17.50 H24 N2 O1.50' _chemical_formula_weight 286.39 _chemical_absolute_configuration unk 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 orthorhombic _symmetry_space_group_name_H-M P21212 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, z' 'x+1/2, -y+1/2, -z' '-x+1/2, y+1/2, -z' _cell_length_a 14.7583(14) _cell_length_b 29.841(3) _cell_length_c 7.5013(8) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 3303.6(6) _cell_formula_units_Z 8 _cell_measurement_temperature 296(2) _cell_measurement_reflns_used 6169 _cell_measurement_theta_min 4.50 _cell_measurement_theta_max 54.87 _exptl_crystal_description needle _exptl_crystal_colour colorless _exptl_crystal_size_max 0.90 _exptl_crystal_size_mid 0.15 _exptl_crystal_size_min 0.10 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.152 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1240 _exptl_absorpt_coefficient_mu 0.074 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.9367 _exptl_absorpt_correction_T_max 0.9927 _exptl_absorpt_process_details sadabs _exptl_special_details ; ? ; _diffrn_ambient_temperature 296(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 'Bruker APEX-II CCD' _diffrn_measurement_method '\f and \w scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 17180 _diffrn_reflns_av_R_equivalents 0.0686 _diffrn_reflns_av_sigmaI/netI 0.0913 _diffrn_reflns_limit_h_min -16 _diffrn_reflns_limit_h_max 19 _diffrn_reflns_limit_k_min -38 _diffrn_reflns_limit_k_max 37 _diffrn_reflns_limit_l_min -8 _diffrn_reflns_limit_l_max 9 _diffrn_reflns_theta_min 1.54 _diffrn_reflns_theta_max 27.55 _reflns_number_total 7464 _reflns_number_gt 5417 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker APEX2' _computing_cell_refinement 'Bruker SAINT' _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^)+(0.0680P)^2^+0.0000P] 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 0.0043(5) _refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^ _refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881' _refine_ls_abs_structure_Flack -0.5(15) _refine_ls_number_reflns 7464 _refine_ls_number_parameters 391 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0879 _refine_ls_R_factor_gt 0.0575 _refine_ls_wR_factor_ref 0.1430 _refine_ls_wR_factor_gt 0.1286 _refine_ls_goodness_of_fit_ref 0.995 _refine_ls_restrained_S_all 0.995 _refine_ls_shift/su_max 0.000 _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 O2 O 0.93409(12) 0.92117(5) 0.3364(2) 0.0280(4) Uani 1 1 d . . . O1 O 0.93565(11) -0.09286(5) -0.1252(2) 0.0258(4) Uani 1 1 d . . . N3 N 0.91447(13) 0.85749(6) 0.1773(3) 0.0227(4) Uani 1 1 d . . . H2 H 0.9176 0.8733 0.0817 0.027 Uiso 1 1 calc R . . N1 N 0.89874(13) -0.03008(6) 0.0309(3) 0.0227(5) Uani 1 1 d . . . H101 H 0.9095 -0.0448 0.1272 0.027 Uiso 1 1 calc R . . C16 C 0.92373(16) 0.87933(7) 0.3368(4) 0.0246(6) Uani 1 1 d . . . C17 C 0.91914(16) 0.85182(7) 0.4914(4) 0.0246(5) Uani 1 1 d . . . H18 H 0.9247 0.8646 0.6039 0.030 Uiso 1 1 calc R . . C18 C 0.90665(16) 0.80691(8) 0.4750(4) 0.0252(5) Uani 1 1 d . . . H19 H 0.9038 0.7894 0.5775 0.030 Uiso 1 1 calc R . . C19 C 0.89784(15) 0.78597(7) 0.3070(4) 0.0229(5) Uani 1 1 d . . . C21 C 0.88205(16) 0.73509(7) 0.2943(4) 0.0246(6) Uani 1 1 d . . . C22 C 0.78243(18) 0.72524(8) 0.3402(4) 0.0316(6) Uani 1 1 d . . . H7 H 0.7750 0.6932 0.3568 0.038 Uiso 1 1 calc R . . H8 H 0.7675 0.7398 0.4519 0.038 Uiso 1 1 calc R . . C23 C 0.71780(17) 0.74087(8) 0.1991(4) 0.0318(6) Uani 1 1 d . . . C28 C 0.61993(19) 0.74465(10) 0.2538(5) 0.0481(9) Uani 1 1 d . . . H9 H 0.6143 0.7663 0.3477 0.072 Uiso 1 1 calc R . . H10 H 0.5988 0.7161 0.2951 0.072 Uiso 1 1 calc R . . H1 H 0.5843 0.7540 0.1533 0.072 Uiso 1 1 calc R . . C20 C 0.90053(15) 0.81213(7) 0.1582(4) 0.0225(5) Uani 1 1 d . . . C27 C 0.89684(16) 0.71995(7) 0.1041(4) 0.0242(5) Uani 1 1 d . . . C29 C 0.94802(18) 0.68503(7) 0.0581(4) 0.0284(6) Uani 1 1 d . . . H6 H 0.9783 0.6703 0.1498 0.034 Uiso 1 1 calc R . . C30 C 0.9617(2) 0.66715(8) -0.1255(4) 0.0379(7) Uani 1 1 d . . . H5 H 0.9217 0.6423 -0.1449 0.057 Uiso 1 1 calc R . . H3 H 1.0233 0.6574 -0.1389 0.057 Uiso 1 1 calc R . . H4 H 0.9489 0.6903 -0.2110 0.057 Uiso 1 1 calc R . . C25 C 0.84330(16) 0.74830(7) -0.0231(4) 0.0260(6) Uani 1 1 d . . . H14 H 0.8457 0.7351 -0.1426 0.031 Uiso 1 1 calc R . . C24 C 0.74588(17) 0.75143(8) 0.0381(4) 0.0304(6) Uani 1 1 d . . . H11 H 0.7030 0.7615 -0.0435 0.036 Uiso 1 1 calc R . . C26 C 0.88700(17) 0.79583(7) -0.0265(4) 0.0263(6) Uani 1 1 d . . . H13 H 0.9448 0.7946 -0.0878 0.032 Uiso 1 1 calc R . . H12 H 0.8479 0.8164 -0.0908 0.032 Uiso 1 1 calc R . . N4 N 0.93837(17) 0.71388(6) 0.4314(3) 0.0346(6) Uani 1 1 d . . . C1 C 0.91133(15) -0.05183(7) -0.1270(4) 0.0234(5) Uani 1 1 d . . . C5 C 0.87019(15) 0.01360(7) 0.0480(4) 0.0228(5) Uani 1 1 d . . . C11 C 0.85775(17) 0.03051(7) 0.2331(4) 0.0245(5) Uani 1 1 d . . . H37 H 0.9160 0.0388 0.2831 0.029 Uiso 1 1 calc R . . H21 H 0.8318 0.0071 0.3070 0.029 Uiso 1 1 calc R . . C10 C 0.79406(16) 0.07178(7) 0.2309(4) 0.0251(6) Uani 1 1 d . . . H8A H 0.7937 0.0859 0.3487 0.030 Uiso 1 1 calc R . . C9 C 0.69862(17) 0.05772(7) 0.1813(4) 0.0285(6) Uani 1 1 d . . . H35 H 0.6633 0.0441 0.2686 0.034 Uiso 1 1 calc R . . C8 C 0.66255(17) 0.06353(8) 0.0224(4) 0.0296(6) Uani 1 1 d . . . C13 C 0.56678(18) 0.05039(9) -0.0207(5) 0.0404(7) Uani 1 1 d . . . H34 H 0.5372 0.0400 0.0855 0.061 Uiso 1 1 calc R . . H33 H 0.5671 0.0269 -0.1080 0.061 Uiso 1 1 calc R . . H20 H 0.5349 0.0759 -0.0673 0.061 Uiso 1 1 calc R . . C7 C 0.71466(17) 0.08467(8) -0.1290(4) 0.0287(6) Uani 1 1 d . . . H22 H 0.6927 0.1149 -0.1476 0.034 Uiso 1 1 calc R . . H32 H 0.7035 0.0678 -0.2374 0.034 Uiso 1 1 calc R . . C6 C 0.81806(16) 0.08617(7) -0.0934(4) 0.0243(5) Uani 1 1 d . . . C12 C 0.82845(15) 0.10459(7) 0.0939(4) 0.0225(5) Uani 1 1 d . . . C14 C 0.85708(16) 0.14601(7) 0.1286(4) 0.0248(5) Uani 1 1 d . . . H23 H 0.8781 0.1625 0.0318 0.030 Uiso 1 1 calc R . . C15 C 0.85924(18) 0.16892(8) 0.3057(4) 0.0313(6) Uani 1 1 d . . . H25 H 0.8054 0.1866 0.3200 0.047 Uiso 1 1 calc R . . H26 H 0.9115 0.1880 0.3122 0.047 Uiso 1 1 calc R . . H24 H 0.8621 0.1469 0.3987 0.047 Uiso 1 1 calc R . . C4 C 0.85427(15) 0.03788(7) -0.1015(4) 0.0222(5) Uani 1 1 d . . . C3 C 0.86841(16) 0.01731(7) -0.2685(4) 0.0244(5) Uani 1 1 d . . . H27 H 0.8584 0.0338 -0.3719 0.029 Uiso 1 1 calc R . . C2 C 0.89651(16) -0.02628(7) -0.2824(4) 0.0243(5) Uani 1 1 d . . . H28 H 0.9058 -0.0390 -0.3941 0.029 Uiso 1 1 calc R . . N2 N 0.85968(15) 0.11150(6) -0.2379(3) 0.0281(5) Uani 1 1 d . . . C1S C 1.0170(2) 0.41374(10) 0.5038(5) 0.0543(9) Uani 1 1 d . . . H40 H 1.0191 0.4432 0.4523 0.081 Uiso 1 1 calc R . . H39 H 1.0763 0.4006 0.5004 0.081 Uiso 1 1 calc R . . H38 H 0.9969 0.4158 0.6253 0.081 Uiso 1 1 calc R . . O1S O 0.95608(14) 0.38675(7) 0.4061(4) 0.0584(7) Uani 1 1 d . . . C5S C 0.8636(2) 0.40144(11) 0.4117(6) 0.0569(10) Uani 1 1 d . . . C4S C 0.8241(3) 0.39866(18) 0.5966(7) 0.0903(15) Uani 1 1 d . . . H34A H 0.8289 0.3685 0.6397 0.136 Uiso 1 1 calc R . . H34B H 0.7615 0.4074 0.5933 0.136 Uiso 1 1 calc R . . H34C H 0.8568 0.4184 0.6746 0.136 Uiso 1 1 calc R . . C2S C 0.8176(3) 0.36778(19) 0.2824(8) 0.108(2) Uani 1 1 d . . . H35A H 0.8480 0.3684 0.1693 0.161 Uiso 1 1 calc R . . H35B H 0.7552 0.3760 0.2663 0.161 Uiso 1 1 calc R . . H35C H 0.8210 0.3381 0.3315 0.161 Uiso 1 1 calc R . . C3S C 0.8550(3) 0.44841(14) 0.3427(9) 0.113(2) Uani 1 1 d . . . H33A H 0.8888 0.4684 0.4177 0.169 Uiso 1 1 calc R . . H33B H 0.7923 0.4571 0.3428 0.169 Uiso 1 1 calc R . . H33C H 0.8782 0.4498 0.2233 0.169 Uiso 1 1 calc R . . H103 H 0.8427 0.1378 -0.2435 0.037(8) Uiso 1 1 d R . . H105 H 0.9333 0.6830 0.4215 0.060(10) Uiso 1 1 d R . . H102 H 0.9178 0.1115 -0.2182 0.053(10) Uiso 1 1 d R . . H104 H 0.9956 0.7171 0.3998 0.071(12) Uiso 1 1 d 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 O2 0.0348(9) 0.0145(7) 0.0347(11) -0.0015(7) 0.0003(8) 0.0001(7) O1 0.0323(9) 0.0142(7) 0.0311(11) -0.0013(7) 0.0020(8) 0.0022(6) N3 0.0248(10) 0.0172(9) 0.0259(12) 0.0021(8) 0.0020(9) 0.0005(7) N1 0.0272(10) 0.0154(9) 0.0255(13) 0.0032(8) -0.0003(9) 0.0012(7) C16 0.0205(11) 0.0204(11) 0.0331(16) -0.0015(10) 0.0004(11) 0.0009(8) C17 0.0262(12) 0.0235(11) 0.0242(14) -0.0042(10) -0.0006(11) 0.0024(9) C18 0.0252(12) 0.0233(11) 0.0271(15) 0.0015(11) 0.0009(11) 0.0003(9) C19 0.0206(11) 0.0195(10) 0.0284(15) 0.0014(10) 0.0003(11) -0.0006(9) C21 0.0288(12) 0.0159(10) 0.0292(15) 0.0015(10) -0.0013(11) -0.0030(9) C22 0.0362(14) 0.0231(11) 0.0356(17) -0.0028(11) 0.0094(13) -0.0086(10) C23 0.0262(12) 0.0207(11) 0.0487(19) -0.0080(12) -0.0011(13) -0.0049(10) C28 0.0306(14) 0.0343(14) 0.079(3) -0.0079(17) 0.0154(16) -0.0053(11) C20 0.0201(11) 0.0160(10) 0.0313(15) -0.0002(10) 0.0010(11) 0.0001(8) C27 0.0267(12) 0.0167(10) 0.0290(15) 0.0026(10) -0.0010(11) -0.0041(9) C29 0.0340(13) 0.0180(10) 0.0332(16) 0.0013(11) 0.0043(12) -0.0019(10) C30 0.0465(16) 0.0225(12) 0.0446(19) -0.0018(13) 0.0064(15) 0.0007(11) C25 0.0337(13) 0.0173(11) 0.0269(15) -0.0019(10) -0.0035(11) -0.0022(9) C24 0.0286(13) 0.0197(11) 0.0428(18) -0.0032(12) -0.0104(12) -0.0019(9) C26 0.0301(12) 0.0171(10) 0.0318(16) 0.0029(10) -0.0015(12) -0.0009(9) N4 0.0497(15) 0.0194(10) 0.0347(15) 0.0025(10) -0.0068(12) 0.0006(10) C1 0.0219(11) 0.0191(10) 0.0292(15) -0.0018(10) 0.0023(11) -0.0028(8) C5 0.0170(11) 0.0174(10) 0.0341(16) -0.0008(10) 0.0008(10) 0.0001(8) C11 0.0281(12) 0.0167(10) 0.0287(15) 0.0029(10) -0.0002(11) 0.0034(9) C10 0.0265(12) 0.0164(10) 0.0325(16) -0.0051(11) 0.0010(11) 0.0026(9) C9 0.0258(12) 0.0195(11) 0.0400(17) -0.0025(11) 0.0101(12) -0.0015(9) C8 0.0249(12) 0.0196(11) 0.0442(18) -0.0073(12) 0.0023(12) -0.0007(9) C13 0.0270(13) 0.0339(14) 0.060(2) -0.0097(14) -0.0007(14) -0.0043(11) C7 0.0290(13) 0.0216(11) 0.0356(16) -0.0028(12) -0.0021(12) 0.0037(9) C6 0.0249(12) 0.0163(10) 0.0317(15) 0.0014(10) 0.0002(11) 0.0018(9) C12 0.0187(10) 0.0192(10) 0.0298(15) 0.0019(11) -0.0009(10) 0.0044(8) C14 0.0234(11) 0.0202(11) 0.0307(15) 0.0013(11) -0.0006(11) 0.0027(9) C15 0.0303(13) 0.0233(12) 0.0404(17) -0.0026(12) -0.0010(13) -0.0001(10) C4 0.0182(10) 0.0188(10) 0.0297(15) -0.0019(10) -0.0015(11) -0.0009(8) C3 0.0272(12) 0.0205(10) 0.0254(15) 0.0034(10) -0.0025(11) -0.0002(9) C2 0.0268(12) 0.0198(11) 0.0263(15) -0.0051(10) 0.0000(11) -0.0005(9) N2 0.0311(12) 0.0183(10) 0.0350(14) 0.0030(9) -0.0016(10) 0.0031(8) C1S 0.0490(19) 0.0497(18) 0.064(2) -0.0014(18) -0.0051(18) -0.0163(15) O1S 0.0358(12) 0.0520(12) 0.087(2) -0.0175(13) -0.0009(13) 0.0039(10) C5S 0.0290(14) 0.0546(18) 0.087(3) 0.006(2) 0.0112(17) 0.0038(14) C4S 0.049(2) 0.130(4) 0.092(3) -0.019(3) 0.020(2) -0.018(2) C2S 0.037(2) 0.159(5) 0.128(5) -0.060(4) -0.005(3) -0.015(3) C3S 0.043(2) 0.081(3) 0.215(7) 0.050(4) 0.002(3) 0.024(2) _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 O2 C16 1.258(3) . ? O1 C1 1.276(3) . ? N3 C16 1.369(3) . ? N3 C20 1.377(3) . ? N3 H2 0.8600 . ? N1 C1 1.363(3) . ? N1 C5 1.376(3) . ? N1 H101 0.8600 . ? C16 C17 1.422(4) . ? C17 C18 1.358(3) . ? C17 H18 0.9300 . ? C18 C19 1.413(4) . ? C18 H19 0.9300 . ? C19 C20 1.362(4) . ? C19 C21 1.539(3) . ? C21 N4 1.466(3) . ? C21 C27 1.512(4) . ? C21 C22 1.538(3) . ? C22 C23 1.499(4) . ? C22 H7 0.9700 . ? C22 H8 0.9700 . ? C23 C24 1.315(4) . ? C23 C28 1.506(4) . ? C28 H9 0.9600 . ? C28 H10 0.9600 . ? C28 H1 0.9600 . ? C20 C26 1.482(4) . ? C27 C29 1.332(3) . ? C27 C25 1.500(3) . ? C29 C30 1.491(4) . ? C29 H6 0.9300 . ? C30 H5 0.9600 . ? C30 H3 0.9600 . ? C30 H4 0.9600 . ? C25 C24 1.512(4) . ? C25 C26 1.558(3) . ? C25 H14 0.9800 . ? C24 H11 0.9300 . ? C26 H13 0.9700 . ? C26 H12 0.9700 . ? N4 H105 0.9277 . ? N4 H104 0.8821 . ? C1 C2 1.410(4) . ? C5 C4 1.356(4) . ? C5 C11 1.488(4) . ? C11 C10 1.549(3) . ? C11 H37 0.9700 . ? C11 H21 0.9700 . ? C10 C12 1.507(3) . ? C10 C9 1.516(3) . ? C10 H8A 0.9800 . ? C9 C8 1.317(4) . ? C9 H35 0.9300 . ? C8 C13 1.502(4) . ? C8 C7 1.510(4) . ? C13 H34 0.9600 . ? C13 H33 0.9600 . ? C13 H20 0.9600 . ? C7 C6 1.550(3) . ? C7 H22 0.9700 . ? C7 H32 0.9700 . ? C6 N2 1.457(3) . ? C6 C12 1.517(4) . ? C6 C4 1.538(3) . ? C12 C14 1.332(3) . ? C14 C15 1.495(4) . ? C14 H23 0.9300 . ? C15 H25 0.9600 . ? C15 H26 0.9600 . ? C15 H24 0.9600 . ? C4 C3 1.411(4) . ? C3 C2 1.369(3) . ? C3 H27 0.9300 . ? C2 H28 0.9300 . ? N2 H103 0.8248 . ? N2 H102 0.8700 . ? C1S O1S 1.412(4) . ? C1S H40 0.9600 . ? C1S H39 0.9600 . ? C1S H38 0.9600 . ? O1S C5S 1.434(4) . ? C5S C3S 1.500(5) . ? C5S C4S 1.506(6) . ? C5S C2S 1.553(6) . ? C4S H34A 0.9600 . ? C4S H34B 0.9600 . ? C4S H34C 0.9600 . ? C2S H35A 0.9600 . ? C2S H35B 0.9600 . ? C2S H35C 0.9600 . ? C3S H33A 0.9600 . ? C3S H33B 0.9600 . ? C3S H33C 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 C16 N3 C20 125.0(2) . . ? C16 N3 H2 117.5 . . ? C20 N3 H2 117.5 . . ? C1 N1 C5 125.0(2) . . ? C1 N1 H101 117.5 . . ? C5 N1 H101 117.5 . . ? O2 C16 N3 118.8(2) . . ? O2 C16 C17 125.5(2) . . ? N3 C16 C17 115.66(19) . . ? C18 C17 C16 120.2(2) . . ? C18 C17 H18 119.9 . . ? C16 C17 H18 119.9 . . ? C17 C18 C19 122.0(3) . . ? C17 C18 H19 119.0 . . ? C19 C18 H19 119.0 . . ? C20 C19 C18 118.3(2) . . ? C20 C19 C21 121.3(2) . . ? C18 C19 C21 120.4(2) . . ? N4 C21 C27 116.8(2) . . ? N4 C21 C19 107.3(2) . . ? C27 C21 C19 109.3(2) . . ? N4 C21 C22 107.6(2) . . ? C27 C21 C22 107.0(2) . . ? C19 C21 C22 108.63(19) . . ? C23 C22 C21 113.0(2) . . ? C23 C22 H7 109.0 . . ? C21 C22 H7 109.0 . . ? C23 C22 H8 109.0 . . ? C21 C22 H8 109.0 . . ? H7 C22 H8 107.8 . . ? C24 C23 C22 121.5(2) . . ? C24 C23 C28 122.3(3) . . ? C22 C23 C28 116.2(3) . . ? C23 C28 H9 109.5 . . ? C23 C28 H10 109.5 . . ? H9 C28 H10 109.5 . . ? C23 C28 H1 109.5 . . ? H9 C28 H1 109.5 . . ? H10 C28 H1 109.5 . . ? C19 C20 N3 118.9(2) . . ? C19 C20 C26 125.0(2) . . ? N3 C20 C26 116.1(2) . . ? C29 C27 C25 125.1(3) . . ? C29 C27 C21 124.0(2) . . ? C25 C27 C21 110.8(2) . . ? C27 C29 C30 126.6(3) . . ? C27 C29 H6 116.7 . . ? C30 C29 H6 116.7 . . ? C29 C30 H5 109.5 . . ? C29 C30 H3 109.5 . . ? H5 C30 H3 109.5 . . ? C29 C30 H4 109.5 . . ? H5 C30 H4 109.5 . . ? H3 C30 H4 109.5 . . ? C27 C25 C24 110.0(2) . . ? C27 C25 C26 107.8(2) . . ? C24 C25 C26 110.01(18) . . ? C27 C25 H14 109.6 . . ? C24 C25 H14 109.6 . . ? C26 C25 H14 109.6 . . ? C23 C24 C25 124.3(2) . . ? C23 C24 H11 117.9 . . ? C25 C24 H11 117.9 . . ? C20 C26 C25 109.8(2) . . ? C20 C26 H13 109.7 . . ? C25 C26 H13 109.7 . . ? C20 C26 H12 109.7 . . ? C25 C26 H12 109.7 . . ? H13 C26 H12 108.2 . . ? C21 N4 H105 109.1 . . ? C21 N4 H104 107.9 . . ? H105 N4 H104 99.4 . . ? O1 C1 N1 119.1(2) . . ? O1 C1 C2 124.8(2) . . ? N1 C1 C2 116.07(19) . . ? C4 C5 N1 118.8(2) . . ? C4 C5 C11 124.7(2) . . ? N1 C5 C11 116.5(2) . . ? C5 C11 C10 109.5(2) . . ? C5 C11 H37 109.8 . . ? C10 C11 H37 109.8 . . ? C5 C11 H21 109.8 . . ? C10 C11 H21 109.8 . . ? H37 C11 H21 108.2 . . ? C12 C10 C9 109.0(2) . . ? C12 C10 C11 108.6(2) . . ? C9 C10 C11 110.26(18) . . ? C12 C10 H8A 109.6 . . ? C9 C10 H8A 109.6 . . ? C11 C10 H8A 109.6 . . ? C8 C9 C10 124.2(2) . . ? C8 C9 H35 117.9 . . ? C10 C9 H35 117.9 . . ? C9 C8 C13 122.8(3) . . ? C9 C8 C7 122.0(2) . . ? C13 C8 C7 115.2(3) . . ? C8 C13 H34 109.5 . . ? C8 C13 H33 109.5 . . ? H34 C13 H33 109.5 . . ? C8 C13 H20 109.5 . . ? H34 C13 H20 109.5 . . ? H33 C13 H20 109.5 . . ? C8 C7 C6 112.6(2) . . ? C8 C7 H22 109.1 . . ? C6 C7 H22 109.1 . . ? C8 C7 H32 109.1 . . ? C6 C7 H32 109.1 . . ? H22 C7 H32 107.8 . . ? N2 C6 C12 117.30(19) . . ? N2 C6 C4 108.1(2) . . ? C12 C6 C4 109.9(2) . . ? N2 C6 C7 107.6(2) . . ? C12 C6 C7 105.6(2) . . ? C4 C6 C7 107.95(18) . . ? C14 C12 C10 125.2(2) . . ? C14 C12 C6 123.3(2) . . ? C10 C12 C6 111.22(19) . . ? C12 C14 C15 127.2(2) . . ? C12 C14 H23 116.4 . . ? C15 C14 H23 116.4 . . ? C14 C15 H25 109.5 . . ? C14 C15 H26 109.5 . . ? H25 C15 H26 109.5 . . ? C14 C15 H24 109.5 . . ? H25 C15 H24 109.5 . . ? H26 C15 H24 109.5 . . ? C5 C4 C3 118.5(2) . . ? C5 C4 C6 121.9(2) . . ? C3 C4 C6 119.6(2) . . ? C2 C3 C4 121.7(2) . . ? C2 C3 H27 119.1 . . ? C4 C3 H27 119.1 . . ? C3 C2 C1 119.9(2) . . ? C3 C2 H28 120.1 . . ? C1 C2 H28 120.1 . . ? C6 N2 H103 113.8 . . ? C6 N2 H102 106.8 . . ? H103 N2 H102 107.9 . . ? O1S C1S H40 109.5 . . ? O1S C1S H39 109.5 . . ? H40 C1S H39 109.5 . . ? O1S C1S H38 109.5 . . ? H40 C1S H38 109.5 . . ? H39 C1S H38 109.5 . . ? C1S O1S C5S 114.6(3) . . ? O1S C5S C3S 110.9(3) . . ? O1S C5S C4S 112.2(3) . . ? C3S C5S C4S 109.7(4) . . ? O1S C5S C2S 101.6(3) . . ? C3S C5S C2S 110.6(4) . . ? C4S C5S C2S 111.7(3) . . ? C5S C4S H34A 109.5 . . ? C5S C4S H34B 109.5 . . ? H34A C4S H34B 109.5 . . ? C5S C4S H34C 109.5 . . ? H34A C4S H34C 109.5 . . ? H34B C4S H34C 109.5 . . ? C5S C2S H35A 109.5 . . ? C5S C2S H35B 109.5 . . ? H35A C2S H35B 109.5 . . ? C5S C2S H35C 109.5 . . ? H35A C2S H35C 109.5 . . ? H35B C2S H35C 109.5 . . ? C5S C3S H33A 109.5 . . ? C5S C3S H33B 109.5 . . ? H33A C3S H33B 109.5 . . ? C5S C3S H33C 109.5 . . ? H33A C3S H33C 109.5 . . ? H33B C3S H33C 109.5 . . ? 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 C20 N3 C16 O2 -178.3(2) . . . . ? C20 N3 C16 C17 0.7(3) . . . . ? O2 C16 C17 C18 179.2(2) . . . . ? N3 C16 C17 C18 0.3(3) . . . . ? C16 C17 C18 C19 0.0(4) . . . . ? C17 C18 C19 C20 -1.1(3) . . . . ? C17 C18 C19 C21 -178.9(2) . . . . ? C20 C19 C21 N4 142.9(2) . . . . ? C18 C19 C21 N4 -39.4(3) . . . . ? C20 C19 C21 C27 15.4(3) . . . . ? C18 C19 C21 C27 -166.9(2) . . . . ? C20 C19 C21 C22 -101.0(3) . . . . ? C18 C19 C21 C22 76.7(3) . . . . ? N4 C21 C22 C23 -173.7(2) . . . . ? C27 C21 C22 C23 -47.5(2) . . . . ? C19 C21 C22 C23 70.5(3) . . . . ? C21 C22 C23 C24 15.5(3) . . . . ? C21 C22 C23 C28 -163.3(2) . . . . ? C18 C19 C20 N3 2.0(3) . . . . ? C21 C19 C20 N3 179.7(2) . . . . ? C18 C19 C20 C26 -176.2(2) . . . . ? C21 C19 C20 C26 1.5(4) . . . . ? C16 N3 C20 C19 -1.9(3) . . . . ? C16 N3 C20 C26 176.5(2) . . . . ? N4 C21 C27 C29 9.3(3) . . . . ? C19 C21 C27 C29 131.3(2) . . . . ? C22 C21 C27 C29 -111.2(3) . . . . ? N4 C21 C27 C25 -173.0(2) . . . . ? C19 C21 C27 C25 -51.0(2) . . . . ? C22 C21 C27 C25 66.5(2) . . . . ? C25 C27 C29 C30 -0.5(4) . . . . ? C21 C27 C29 C30 176.9(2) . . . . ? C29 C27 C25 C24 127.6(3) . . . . ? C21 C27 C25 C24 -50.0(2) . . . . ? C29 C27 C25 C26 -112.4(3) . . . . ? C21 C27 C25 C26 69.9(3) . . . . ? C22 C23 C24 C25 1.2(4) . . . . ? C28 C23 C24 C25 179.9(2) . . . . ? C27 C25 C24 C23 15.9(3) . . . . ? C26 C25 C24 C23 -102.7(3) . . . . ? C19 C20 C26 C25 15.7(3) . . . . ? N3 C20 C26 C25 -162.56(19) . . . . ? C27 C25 C26 C20 -49.3(3) . . . . ? C24 C25 C26 C20 70.7(3) . . . . ? C5 N1 C1 O1 -178.1(2) . . . . ? C5 N1 C1 C2 2.3(3) . . . . ? C1 N1 C5 C4 -1.1(3) . . . . ? C1 N1 C5 C11 178.0(2) . . . . ? C4 C5 C11 C10 19.8(3) . . . . ? N1 C5 C11 C10 -159.23(19) . . . . ? C5 C11 C10 C12 -50.9(3) . . . . ? C5 C11 C10 C9 68.5(3) . . . . ? C12 C10 C9 C8 16.9(3) . . . . ? C11 C10 C9 C8 -102.3(3) . . . . ? C10 C9 C8 C13 -178.2(2) . . . . ? C10 C9 C8 C7 0.9(4) . . . . ? C9 C8 C7 C6 15.7(3) . . . . ? C13 C8 C7 C6 -165.2(2) . . . . ? C8 C7 C6 N2 -173.78(19) . . . . ? C8 C7 C6 C12 -47.7(2) . . . . ? C8 C7 C6 C4 69.8(3) . . . . ? C9 C10 C12 C14 122.2(2) . . . . ? C11 C10 C12 C14 -117.6(3) . . . . ? C9 C10 C12 C6 -52.3(2) . . . . ? C11 C10 C12 C6 67.9(2) . . . . ? N2 C6 C12 C14 13.6(3) . . . . ? C4 C6 C12 C14 137.5(2) . . . . ? C7 C6 C12 C14 -106.2(2) . . . . ? N2 C6 C12 C10 -171.79(19) . . . . ? C4 C6 C12 C10 -47.8(2) . . . . ? C7 C6 C12 C10 68.4(2) . . . . ? C10 C12 C14 C15 -1.6(4) . . . . ? C6 C12 C14 C15 172.2(2) . . . . ? N1 C5 C4 C3 -0.5(3) . . . . ? C11 C5 C4 C3 -179.5(2) . . . . ? N1 C5 C4 C6 177.1(2) . . . . ? C11 C5 C4 C6 -1.9(3) . . . . ? N2 C6 C4 C5 144.3(2) . . . . ? C12 C6 C4 C5 15.2(3) . . . . ? C7 C6 C4 C5 -99.6(3) . . . . ? N2 C6 C4 C3 -38.1(3) . . . . ? C12 C6 C4 C3 -167.2(2) . . . . ? C7 C6 C4 C3 78.0(3) . . . . ? C5 C4 C3 C2 0.8(3) . . . . ? C6 C4 C3 C2 -176.9(2) . . . . ? C4 C3 C2 C1 0.5(4) . . . . ? O1 C1 C2 C3 178.5(2) . . . . ? N1 C1 C2 C3 -2.0(3) . . . . ? C1S O1S C5S C3S 58.1(5) . . . . ? C1S O1S C5S C4S -64.8(4) . . . . ? C1S O1S C5S C2S 175.7(3) . . . . ? _diffrn_measured_fraction_theta_max 0.989 _diffrn_reflns_theta_full 27.55 _diffrn_measured_fraction_theta_full 0.989 _refine_diff_density_max 0.289 _refine_diff_density_min -0.260 _refine_diff_density_rms 0.057 _database_code_depnum_ccdc_archive 'CCDC 958407' ####################################################################### # # Cambridge Crystallographic Data Centre # CCDC # ####################################################################### # # This CIF contains data from an original supplementary publication # deposited with the CCDC, and may include chemical, crystal, # experimental, refinement, atomic coordinates, # anisotropic displacement parameters and molecular geometry data, # as required by the journal to which it was submitted. # # This CIF is provided on the understanding that it is used for bona # fide research purposes only. It may contain copyright material # of the CCDC or of third parties, and may not be copied or further # disseminated in any form, whether machine-readable or not, # except for the purpose of generating routine backup copies # on your local computer system. # # For further information on the CCDC, data deposition and # data retrieval see: # www.ccdc.cam.ac.uk # # Bona fide researchers may freely download Mercury and enCIFer # from this site to visualise CIF-encoded structures and # to carry out CIF format checking respectively. # data_S2.CIF _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common 'Hup A Form S4' _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C18 H25 N2 O' _chemical_formula_weight 285.40 _chemical_absolute_configuration unk 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 monoclinic _symmetry_space_group_name_H-M P21 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y+1/2, -z' _cell_length_a 8.0666(6) _cell_length_b 16.2940(12) _cell_length_c 12.7096(10) _cell_angle_alpha 90.00 _cell_angle_beta 94.054(4) _cell_angle_gamma 90.00 _cell_volume 1666.3(2) _cell_formula_units_Z 4 _cell_measurement_temperature 100(2) _cell_measurement_reflns_used 6169 _cell_measurement_theta_min 4.50 _cell_measurement_theta_max 54.87 _exptl_crystal_description column _exptl_crystal_colour colorless _exptl_crystal_size_max 0.35 _exptl_crystal_size_mid 0.33 _exptl_crystal_size_min 0.26 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.138 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 620 _exptl_absorpt_coefficient_mu 0.071 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.9757 _exptl_absorpt_correction_T_max 0.9819 _exptl_absorpt_process_details sadabs _exptl_special_details ; ? ; _diffrn_ambient_temperature 100(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 'Bruker APEX-II CCD' _diffrn_measurement_method '\f and \w scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 18770 _diffrn_reflns_av_R_equivalents 0.0363 _diffrn_reflns_av_sigmaI/netI 0.0426 _diffrn_reflns_limit_h_min -11 _diffrn_reflns_limit_h_max 11 _diffrn_reflns_limit_k_min -23 _diffrn_reflns_limit_k_max 23 _diffrn_reflns_limit_l_min -16 _diffrn_reflns_limit_l_max 17 _diffrn_reflns_theta_min 1.61 _diffrn_reflns_theta_max 30.28 _reflns_number_total 9542 _reflns_number_gt 9276 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker APEX2' _computing_cell_refinement 'Bruker SAINT' _computing_data_reduction 'Bruker SAINT' _computing_structure_solution 'SHELXS-97 (Sheldrick, 2008)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 2008)' _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^)+(0.0727P)^2^+0.2819P] 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 0.0043(5) _refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^ _refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881' _refine_ls_abs_structure_Flack 1.0(7) _refine_ls_number_reflns 9542 _refine_ls_number_parameters 399 _refine_ls_number_restraints 1 _refine_ls_R_factor_all 0.0433 _refine_ls_R_factor_gt 0.0422 _refine_ls_wR_factor_ref 0.1186 _refine_ls_wR_factor_gt 0.1168 _refine_ls_goodness_of_fit_ref 1.042 _refine_ls_restrained_S_all 1.042 _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 C15 C 0.6789(2) 0.50871(15) 0.70988(15) 0.0462(4) Uani 1 1 d . A 1 H1 H 0.7575 0.4735 0.6756 0.069 Uiso 1 1 calc R A 1 H5 H 0.7276 0.5634 0.7214 0.069 Uiso 1 1 calc R A 1 H6 H 0.5757 0.5133 0.6647 0.069 Uiso 1 1 calc R A 1 C14 C 0.64201(17) 0.47206(9) 0.81368(12) 0.0273(3) Uani 1 1 d . A 1 H7 H 0.7292 0.4741 0.8679 0.033 Uiso 1 1 calc R A 1 C12 C 0.50132(15) 0.43691(7) 0.83879(9) 0.0169(2) Uani 1 1 d . A 1 C10 C 0.34630(15) 0.42581(7) 0.76621(9) 0.0165(2) Uani 1 1 d . A 1 H9 H 0.3599 0.4566 0.6993 0.020 Uiso 1 1 calc R A 1 C11 C 0.32518(16) 0.33394(7) 0.74045(9) 0.0183(2) Uani 1 1 d . A 1 H14 H 0.2122 0.3240 0.7073 0.022 Uiso 1 1 calc R A 1 H13 H 0.4064 0.3175 0.6895 0.022 Uiso 1 1 calc R A 1 C5 C 0.35129(14) 0.28298(7) 0.83877(9) 0.0151(2) Uani 1 1 d . A 1 N1 N 0.30418(13) 0.20244(6) 0.82881(8) 0.01597(18) Uani 1 1 d . A 1 H1A H 0.2608 0.1863 0.7668 0.019 Uiso 1 1 calc R A 1 C1 C 0.31907(14) 0.14467(7) 0.90780(9) 0.0157(2) Uani 1 1 d . A 1 O1 O 0.27075(12) 0.07202(5) 0.88893(7) 0.01992(17) Uani 1 1 d . A 1 C13 C 0.05360(18) 0.51633(10) 0.96811(12) 0.0296(3) Uani 1 1 d . A 1 H4 H -0.0296 0.5322 0.9119 0.044 Uiso 1 1 calc R A 1 H20 H 0.0930 0.5653 1.0070 0.044 Uiso 1 1 calc R A 1 H3 H 0.0035 0.4782 1.0164 0.044 Uiso 1 1 calc R A 1 C8 C 0.19732(15) 0.47524(7) 0.92066(10) 0.0185(2) Uani 1 1 d . A 1 C7 C 0.34345(15) 0.45450(7) 0.99619(9) 0.0180(2) Uani 1 1 d . A 1 H19 H 0.3027 0.4250 1.0573 0.022 Uiso 1 1 calc R A 1 H18 H 0.3956 0.5062 1.0227 0.022 Uiso 1 1 calc R A 1 C6 C 0.47698(15) 0.40139(7) 0.94770(9) 0.0158(2) Uani 1 1 d . A 1 C9 C 0.19799(15) 0.45988(7) 0.81784(10) 0.0184(2) Uani 1 1 d . A 1 H8 H 0.0997 0.4710 0.7745 0.022 Uiso 1 1 calc R A 1 C2 C 0.38978(16) 0.17410(7) 1.00708(9) 0.0180(2) Uani 1 1 d . A 1 H11 H 0.4042 0.1377 1.0654 0.022 Uiso 1 1 calc R A 1 C3 C 0.43694(15) 0.25473(7) 1.01844(9) 0.0174(2) Uani 1 1 d . A 1 H10 H 0.4830 0.2730 1.0852 0.021 Uiso 1 1 calc R A 1 C4 C 0.41927(14) 0.31208(7) 0.93369(9) 0.01518(19) Uani 1 1 d . A 1 N2 N 0.62229(14) 0.40222(7) 1.02355(9) 0.0215(2) Uani 1 1 d . A 1 O2 O 1.15621(13) 1.15703(5) 0.63849(7) 0.02269(19) Uani 1 1 d . B 1 C16 C 1.11495(15) 1.08402(7) 0.61557(9) 0.0169(2) Uani 1 1 d . B 1 N3 N 1.12658(13) 1.02412(6) 0.69194(8) 0.01561(18) Uani 1 1 d . B 1 H27 H 1.1626 1.0389 0.7561 0.019 Uiso 1 1 calc R B 1 C20 C 1.08629(14) 0.94320(6) 0.67553(9) 0.01437(19) Uani 1 1 d . B 1 C26 C 1.10611(16) 0.88814(7) 0.77010(9) 0.0181(2) Uani 1 1 d . B 1 H28 H 1.0594 0.9154 0.8310 0.022 Uiso 1 1 calc R B 1 H29 H 1.2257 0.8780 0.7883 0.022 Uiso 1 1 calc R B 1 C25 C 1.01633(16) 0.80561(7) 0.74780(9) 0.0200(2) Uani 1 1 d . B 1 H39 H 1.0529 0.7651 0.8038 0.024 Uiso 1 1 calc R B 1 C24 C 0.82961(17) 0.81724(9) 0.74655(10) 0.0247(2) Uani 1 1 d . B 1 H24 H 0.7811 0.8207 0.8124 0.030 Uiso 1 1 calc R B 1 C23 C 0.72926(16) 0.82289(8) 0.65890(11) 0.0247(2) Uani 1 1 d . B 1 C28 C 0.54481(19) 0.83543(13) 0.66074(16) 0.0404(4) Uani 1 1 d . B 1 H40 H 0.5143 0.8369 0.7340 0.061 Uiso 1 1 calc R B 1 H22 H 0.4863 0.7901 0.6234 0.061 Uiso 1 1 calc R B 1 H23 H 0.5136 0.8874 0.6260 0.061 Uiso 1 1 calc R B 1 C27 C 1.06485(15) 0.77507(7) 0.64250(9) 0.0172(2) Uani 1 1 d . B 1 C21 C 0.98533(14) 0.82722(7) 0.55289(9) 0.01513(19) Uani 1 1 d . B 1 C19 C 1.02970(14) 0.91703(6) 0.57647(9) 0.01420(19) Uani 1 1 d . B 1 C17 C 1.05334(16) 1.05743(7) 0.51294(9) 0.0186(2) Uani 1 1 d . B 1 H26 H 1.0410 1.0958 0.4567 0.022 Uiso 1 1 calc R B 1 C18 C 1.01217(15) 0.97690(7) 0.49563(9) 0.0166(2) Uani 1 1 d . B 1 H25 H 0.9704 0.9606 0.4271 0.020 Uiso 1 1 calc R B 1 N4 N 1.03359(14) 0.80816(6) 0.44692(8) 0.01955(19) Uani 1 1 d . B 1 C22 C 0.79476(15) 0.81653(8) 0.55145(10) 0.0207(2) Uani 1 1 d . B 1 H34 H 0.7407 0.8590 0.5051 0.025 Uiso 1 1 calc R B 1 H33 H 0.7643 0.7622 0.5209 0.025 Uiso 1 1 calc R B 1 C29 C 1.17094(17) 0.71360(7) 0.62833(11) 0.0222(2) Uani 1 1 d . B 1 H35 H 1.1943 0.7020 0.5576 0.027 Uiso 1 1 calc R B 1 C30 C 1.2572(2) 0.66092(9) 0.71279(14) 0.0348(3) Uani 1 1 d . B 1 H37 H 1.2154 0.6745 0.7812 0.052 Uiso 1 1 calc R B 1 H36 H 1.3772 0.6711 0.7154 0.052 Uiso 1 1 calc R B 1 H38 H 1.2352 0.6029 0.6968 0.052 Uiso 1 1 calc R B 1 C1S C 0.9249(2) 0.25437(11) 0.93946(13) 0.0350(3) Uani 1 1 d . C 1 H41 H 0.8362 0.2505 0.9881 0.052 Uiso 1 1 calc R C 1 H47 H 0.9824 0.3070 0.9497 0.052 Uiso 1 1 calc R C 1 H48 H 1.0041 0.2094 0.9534 0.052 Uiso 1 1 calc R C 1 C2S C 0.8501(2) 0.24844(9) 0.82649(12) 0.0306(3) Uani 1 1 d . C 1 H50 H 0.7639 0.2913 0.8143 0.037 Uiso 1 1 calc R C 1 H49 H 0.9379 0.2587 0.7774 0.037 Uiso 1 1 calc R C 1 C3S C 0.77368(18) 0.16513(9) 0.80369(11) 0.0252(2) Uani 1 1 d . C 1 H51 H 0.8611 0.1228 0.8152 0.030 Uiso 1 1 calc R C 1 H52 H 0.6886 0.1547 0.8545 0.030 Uiso 1 1 calc R C 1 C4S C 0.6953(2) 0.15624(10) 0.69489(14) 0.0234(4) Uani 0.800(6) 1 d P C 1 H53 H 0.7813 0.1652 0.6442 0.028 Uiso 1 1 calc R C 1 H46 H 0.6104 0.1997 0.6828 0.028 Uiso 1 1 calc R C 1 C5S C 0.6136(3) 0.07320(12) 0.67172(16) 0.0438(4) Uani 1 1 d . . . H45 H 0.5231 0.0649 0.7194 0.053 Uiso 1 1 calc R C 1 H44 H 0.6966 0.0291 0.6858 0.053 Uiso 1 1 calc R C 1 C6S C 0.5409(3) 0.06728(17) 0.55453(18) 0.0570(5) Uani 1 1 d . C . H54 H 0.4686 0.1146 0.5380 0.085 Uiso 1 1 calc R . . H42 H 0.4764 0.0165 0.5447 0.085 Uiso 1 1 calc R . . H43 H 0.6321 0.0670 0.5076 0.085 Uiso 1 1 calc R . . H1' H 0.9925 0.7588 0.4241 0.024(4) Uiso 1 1 d R . . H2' H 1.1463 0.8056 0.4441 0.017(4) Uiso 1 1 d R . . H3' H 0.6601 0.4552 1.0343 0.033(5) Uiso 1 1 d R . . H4' H 0.7179 0.3739 0.9948 0.044(6) Uiso 1 1 d R . . C4S' C 0.6662(8) 0.2094(4) 0.6454(5) 0.0218(17) Uani 0.200(6) 1 d P C 2 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 C15 0.0362(8) 0.0649(12) 0.0381(9) 0.0173(9) 0.0075(7) -0.0160(8) C14 0.0237(6) 0.0306(7) 0.0274(6) 0.0040(5) -0.0003(5) -0.0058(5) C12 0.0212(5) 0.0129(4) 0.0160(5) -0.0007(4) -0.0024(4) -0.0013(4) C10 0.0231(5) 0.0124(4) 0.0132(5) 0.0012(4) -0.0038(4) -0.0017(4) C11 0.0285(6) 0.0124(5) 0.0128(5) 0.0017(4) -0.0064(4) -0.0007(4) C5 0.0205(5) 0.0108(4) 0.0132(5) 0.0000(4) -0.0042(4) -0.0010(4) N1 0.0233(5) 0.0108(4) 0.0129(4) -0.0005(3) -0.0051(3) -0.0012(3) C1 0.0201(5) 0.0112(4) 0.0151(5) -0.0001(4) -0.0039(4) 0.0001(4) O1 0.0297(4) 0.0111(4) 0.0178(4) 0.0008(3) -0.0062(3) -0.0028(3) C13 0.0240(6) 0.0330(7) 0.0315(7) -0.0068(6) 0.0008(5) 0.0027(5) C8 0.0195(5) 0.0146(5) 0.0212(5) 0.0001(4) -0.0014(4) -0.0023(4) C7 0.0243(5) 0.0146(5) 0.0146(5) -0.0021(4) -0.0027(4) -0.0009(4) C6 0.0204(5) 0.0117(4) 0.0142(5) -0.0008(4) -0.0059(4) -0.0010(4) C9 0.0187(5) 0.0144(5) 0.0213(5) 0.0019(4) -0.0050(4) -0.0012(4) C2 0.0259(6) 0.0139(5) 0.0131(5) 0.0014(4) -0.0052(4) -0.0007(4) C3 0.0253(5) 0.0136(5) 0.0124(5) -0.0001(4) -0.0057(4) -0.0004(4) C4 0.0200(5) 0.0113(4) 0.0134(5) -0.0006(4) -0.0048(4) -0.0005(4) N2 0.0260(5) 0.0151(4) 0.0214(5) -0.0026(4) -0.0119(4) -0.0012(4) O2 0.0359(5) 0.0111(4) 0.0195(4) 0.0001(3) -0.0094(4) -0.0019(3) C16 0.0221(5) 0.0116(5) 0.0160(5) -0.0005(4) -0.0051(4) 0.0013(4) N3 0.0221(4) 0.0109(4) 0.0129(4) -0.0016(3) -0.0052(3) -0.0004(3) C20 0.0188(5) 0.0109(4) 0.0128(5) -0.0005(4) -0.0036(4) 0.0001(4) C26 0.0282(6) 0.0134(5) 0.0117(5) 0.0011(4) -0.0047(4) -0.0022(4) C25 0.0306(6) 0.0152(5) 0.0136(5) 0.0020(4) -0.0024(4) -0.0032(4) C24 0.0308(6) 0.0237(6) 0.0202(5) 0.0004(5) 0.0060(5) -0.0071(5) C23 0.0233(5) 0.0238(6) 0.0271(6) -0.0003(5) 0.0031(5) -0.0058(5) C28 0.0227(6) 0.0517(10) 0.0474(9) 0.0059(8) 0.0067(6) -0.0046(6) C27 0.0239(5) 0.0108(4) 0.0159(5) 0.0004(4) -0.0049(4) -0.0039(4) C21 0.0202(5) 0.0121(4) 0.0123(4) -0.0014(3) -0.0038(4) -0.0016(4) C19 0.0185(5) 0.0115(4) 0.0121(4) -0.0008(3) -0.0030(4) -0.0005(3) C17 0.0278(6) 0.0132(5) 0.0140(5) 0.0015(4) -0.0056(4) 0.0004(4) C18 0.0233(5) 0.0137(5) 0.0121(4) -0.0011(4) -0.0039(4) 0.0003(4) N4 0.0297(5) 0.0149(4) 0.0136(4) -0.0043(3) -0.0014(4) -0.0009(4) C22 0.0212(5) 0.0193(5) 0.0206(5) -0.0014(4) -0.0039(4) -0.0040(4) C29 0.0276(6) 0.0131(5) 0.0250(6) 0.0013(4) -0.0044(5) -0.0012(4) C30 0.0435(8) 0.0200(6) 0.0392(8) 0.0090(6) -0.0079(6) 0.0064(5) C1S 0.0346(8) 0.0342(8) 0.0362(8) -0.0018(6) 0.0029(6) 0.0059(6) C2S 0.0337(7) 0.0256(6) 0.0328(7) 0.0023(5) 0.0043(6) 0.0016(5) C3S 0.0300(6) 0.0222(6) 0.0235(6) 0.0026(5) 0.0028(5) 0.0023(5) C4S 0.0213(8) 0.0213(8) 0.0271(8) 0.0020(6) -0.0007(6) 0.0026(5) C5S 0.0440(9) 0.0368(9) 0.0505(10) -0.0011(8) 0.0022(8) -0.0067(7) C6S 0.0591(13) 0.0607(13) 0.0498(11) 0.0006(10) -0.0055(9) -0.0089(11) C4S' 0.022(3) 0.028(3) 0.016(3) 0.009(2) 0.005(2) -0.007(2) _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 C15 C14 1.497(2) . ? C15 H1 0.9800 . ? C15 H5 0.9800 . ? C15 H6 0.9800 . ? C14 C12 1.3301(17) . ? C14 H7 0.9500 . ? C12 C10 1.5114(16) . ? C12 C6 1.5258(16) . ? C10 C9 1.5104(17) . ? C10 C11 1.5392(16) . ? C10 H9 1.0000 . ? C11 C5 1.5027(15) . ? C11 H14 0.9900 . ? C11 H13 0.9900 . ? C5 N1 1.3696(14) . ? C5 C4 1.3738(15) . ? N1 C1 1.3751(15) . ? N1 H1A 0.8800 . ? C1 O1 1.2639(14) . ? C1 C2 1.4303(15) . ? C13 C8 1.5016(18) . ? C13 H4 0.9800 . ? C13 H20 0.9800 . ? C13 H3 0.9800 . ? C8 C9 1.3309(17) . ? C8 C7 1.5051(16) . ? C7 C6 1.5436(17) . ? C7 H19 0.9900 . ? C7 H18 0.9900 . ? C6 N2 1.4641(14) . ? C6 C4 1.5344(16) . ? C9 H8 0.9500 . ? C2 C3 1.3724(16) . ? C2 H11 0.9500 . ? C3 C4 1.4255(16) . ? C3 H10 0.9500 . ? N2 H3' 0.9225 . ? N2 H4' 0.9904 . ? O2 C16 1.2637(14) . ? C16 N3 1.3749(14) . ? C16 C17 1.4299(16) . ? N3 C20 1.3704(14) . ? N3 H27 0.8800 . ? C20 C19 1.3763(14) . ? C20 C26 1.4994(15) . ? C26 C25 1.5440(16) . ? C26 H28 0.9900 . ? C26 H29 0.9900 . ? C25 C27 1.5053(17) . ? C25 C24 1.5170(19) . ? C25 H39 1.0000 . ? C24 C23 1.333(2) . ? C24 H24 0.9500 . ? C23 C22 1.5023(18) . ? C23 C28 1.504(2) . ? C28 H40 0.9800 . ? C28 H22 0.9800 . ? C28 H23 0.9800 . ? C27 C29 1.3378(17) . ? C27 C21 1.5255(16) . ? C21 N4 1.4616(14) . ? C21 C19 1.5311(15) . ? C21 C22 1.5459(16) . ? C19 C18 1.4167(15) . ? C17 C18 1.3675(16) . ? C17 H26 0.9500 . ? C18 H25 0.9500 . ? N4 H1' 0.9101 . ? N4 H2' 0.9132 . ? C22 H34 0.9900 . ? C22 H33 0.9900 . ? C29 C30 1.5059(19) . ? C29 H35 0.9500 . ? C30 H37 0.9800 . ? C30 H36 0.9800 . ? C30 H38 0.9800 . ? C1S C2S 1.521(2) . ? C1S H41 0.9800 . ? C1S H47 0.9800 . ? C1S H48 0.9800 . ? C2S C3S 1.511(2) . ? C2S H50 0.9900 . ? C2S H49 0.9900 . ? C3S C4S 1.486(2) . ? C3S H51 0.9900 . ? C3S H52 0.9900 . ? C4S C5S 1.525(2) . ? C4S H53 0.9900 . ? C4S H46 0.9900 . ? C5S C6S 1.565(3) . ? C5S H45 0.9900 . ? C5S H44 0.9900 . ? C6S H54 0.9800 . ? C6S H42 0.9800 . ? C6S H43 0.9800 . ? 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 C12 C14 C15 127.54(13) . . ? C12 C14 H7 116.2 . . ? C15 C14 H7 116.2 . . ? C14 C12 C10 126.04(11) . . ? C14 C12 C6 123.21(11) . . ? C10 C12 C6 110.75(10) . . ? C9 C10 C12 109.72(9) . . ? C9 C10 C11 111.76(10) . . ? C12 C10 C11 108.70(9) . . ? C9 C10 H9 108.9 . . ? C12 C10 H9 108.9 . . ? C11 C10 H9 108.9 . . ? C5 C11 C10 110.71(9) . . ? C5 C11 H14 109.5 . . ? C10 C11 H14 109.5 . . ? C5 C11 H13 109.5 . . ? C10 C11 H13 109.5 . . ? H14 C11 H13 108.1 . . ? N1 C5 C4 120.18(10) . . ? N1 C5 C11 115.53(9) . . ? C4 C5 C11 124.28(10) . . ? C5 N1 C1 125.38(10) . . ? C5 N1 H1A 117.3 . . ? C1 N1 H1A 117.3 . . ? O1 C1 N1 119.52(10) . . ? O1 C1 C2 125.43(11) . . ? N1 C1 C2 115.05(10) . . ? C9 C8 C13 122.35(12) . . ? C9 C8 C7 121.78(11) . . ? C13 C8 C7 115.85(11) . . ? C8 C7 C6 114.11(10) . . ? C8 C7 H19 108.7 . . ? C6 C7 H19 108.7 . . ? C8 C7 H18 108.7 . . ? C6 C7 H18 108.7 . . ? H19 C7 H18 107.6 . . ? N2 C6 C12 116.45(10) . . ? N2 C6 C4 107.90(9) . . ? C12 C6 C4 108.17(9) . . ? N2 C6 C7 106.30(9) . . ? C12 C6 C7 106.72(9) . . ? C4 C6 C7 111.31(10) . . ? C8 C9 C10 123.65(11) . . ? C8 C9 H8 118.2 . . ? C10 C9 H8 118.2 . . ? C3 C2 C1 120.26(10) . . ? C3 C2 H11 119.9 . . ? C1 C2 H11 119.9 . . ? C2 C3 C4 122.40(10) . . ? C2 C3 H10 118.8 . . ? C4 C3 H10 118.8 . . ? C5 C4 C3 116.72(10) . . ? C5 C4 C6 121.89(10) . . ? C3 C4 C6 121.38(9) . . ? H3' N2 H4' 103.5 . . ? O2 C16 N3 120.12(10) . . ? O2 C16 C17 124.36(10) . . ? N3 C16 C17 115.52(10) . . ? C20 N3 C16 124.89(10) . . ? C20 N3 H27 117.6 . . ? C16 N3 H27 117.6 . . ? N3 C20 C19 119.81(10) . . ? N3 C20 C26 116.30(9) . . ? C19 C20 C26 123.88(10) . . ? C20 C26 C25 110.61(9) . . ? C20 C26 H28 109.5 . . ? C25 C26 H28 109.5 . . ? C20 C26 H29 109.5 . . ? C25 C26 H29 109.5 . . ? H28 C26 H29 108.1 . . ? C27 C25 C24 110.63(10) . . ? C27 C25 C26 107.64(10) . . ? C24 C25 C26 110.22(10) . . ? C27 C25 H39 109.4 . . ? C24 C25 H39 109.4 . . ? C26 C25 H39 109.4 . . ? C23 C24 C25 124.13(12) . . ? C23 C24 H24 117.9 . . ? C25 C24 H24 117.9 . . ? C24 C23 C22 121.54(12) . . ? C24 C23 C28 122.64(14) . . ? C22 C23 C28 115.82(13) . . ? C29 C27 C25 125.19(11) . . ? C29 C27 C21 123.76(11) . . ? C25 C27 C21 110.95(10) . . ? N4 C21 C27 116.38(10) . . ? N4 C21 C19 108.04(9) . . ? C27 C21 C19 107.82(8) . . ? N4 C21 C22 107.13(9) . . ? C27 C21 C22 108.15(9) . . ? C19 C21 C22 109.18(9) . . ? C20 C19 C18 117.37(10) . . ? C20 C19 C21 122.22(9) . . ? C18 C19 C21 120.42(9) . . ? C18 C17 C16 120.16(10) . . ? C18 C17 H26 119.9 . . ? C16 C17 H26 119.9 . . ? C17 C18 C19 122.23(10) . . ? C17 C18 H25 118.9 . . ? C19 C18 H25 118.9 . . ? H1' N4 H2' 106.8 . . ? C23 C22 C21 113.25(10) . . ? C23 C22 H34 108.9 . . ? C21 C22 H34 108.9 . . ? C23 C22 H33 108.9 . . ? C21 C22 H33 108.9 . . ? H34 C22 H33 107.7 . . ? C27 C29 C30 126.76(13) . . ? C27 C29 H35 116.6 . . ? C30 C29 H35 116.6 . . ? C3S C2S C1S 111.56(13) . . ? C3S C2S H50 109.3 . . ? C1S C2S H50 109.3 . . ? C3S C2S H49 109.3 . . ? C1S C2S H49 109.3 . . ? H50 C2S H49 108.0 . . ? C4S C3S C2S 114.02(12) . . ? C4S C3S H51 108.7 . . ? C2S C3S H51 108.7 . . ? C4S C3S H52 108.7 . . ? C2S C3S H52 108.7 . . ? H51 C3S H52 107.6 . . ? C3S C4S C5S 114.57(14) . . ? C3S C4S H53 108.6 . . ? C5S C4S H53 108.6 . . ? C3S C4S H46 108.6 . . ? C5S C4S H46 108.6 . . ? H53 C4S H46 107.6 . . ? C4S C5S C6S 111.50(17) . . ? C4S C5S H45 109.3 . . ? C6S C5S H45 109.3 . . ? C4S C5S H44 109.3 . . ? C6S C5S H44 109.3 . . ? H45 C5S H44 108.0 . . ? C5S C6S H54 109.5 . . ? C5S C6S H42 109.5 . . ? H54 C6S H42 109.5 . . ? C5S C6S H43 109.5 . . ? H54 C6S H43 109.5 . . ? H42 C6S H43 109.5 . . ? 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 C15 C14 C12 C10 0.5(3) . . . . ? C15 C14 C12 C6 -179.95(17) . . . . ? C14 C12 C10 C9 -127.46(14) . . . . ? C6 C12 C10 C9 52.90(12) . . . . ? C14 C12 C10 C11 110.05(14) . . . . ? C6 C12 C10 C11 -69.59(12) . . . . ? C9 C10 C11 C5 -75.29(12) . . . . ? C12 C10 C11 C5 45.95(13) . . . . ? C10 C11 C5 N1 167.78(10) . . . . ? C10 C11 C5 C4 -13.04(17) . . . . ? C4 C5 N1 C1 -0.24(18) . . . . ? C11 C5 N1 C1 178.97(11) . . . . ? C5 N1 C1 O1 179.90(11) . . . . ? C5 N1 C1 C2 0.19(17) . . . . ? C9 C8 C7 C6 -10.11(16) . . . . ? C13 C8 C7 C6 171.56(11) . . . . ? C14 C12 C6 N2 -4.31(17) . . . . ? C10 C12 C6 N2 175.34(10) . . . . ? C14 C12 C6 C4 -125.95(13) . . . . ? C10 C12 C6 C4 53.70(12) . . . . ? C14 C12 C6 C7 114.18(14) . . . . ? C10 C12 C6 C7 -66.18(11) . . . . ? C8 C7 C6 N2 168.24(10) . . . . ? C8 C7 C6 C12 43.31(12) . . . . ? C8 C7 C6 C4 -74.52(12) . . . . ? C13 C8 C9 C10 174.21(12) . . . . ? C7 C8 C9 C10 -4.01(18) . . . . ? C12 C10 C9 C8 -17.33(16) . . . . ? C11 C10 C9 C8 103.33(13) . . . . ? O1 C1 C2 C3 -179.59(12) . . . . ? N1 C1 C2 C3 0.11(17) . . . . ? C1 C2 C3 C4 -0.35(19) . . . . ? N1 C5 C4 C3 -0.01(17) . . . . ? C11 C5 C4 C3 -179.15(11) . . . . ? N1 C5 C4 C6 178.74(10) . . . . ? C11 C5 C4 C6 -0.40(18) . . . . ? C2 C3 C4 C5 0.30(18) . . . . ? C2 C3 C4 C6 -178.46(11) . . . . ? N2 C6 C4 C5 -146.05(11) . . . . ? C12 C6 C4 C5 -19.28(15) . . . . ? C7 C6 C4 C5 97.67(13) . . . . ? N2 C6 C4 C3 32.63(15) . . . . ? C12 C6 C4 C3 159.41(11) . . . . ? C7 C6 C4 C3 -83.64(13) . . . . ? O2 C16 N3 C20 -179.55(11) . . . . ? C17 C16 N3 C20 0.97(17) . . . . ? C16 N3 C20 C19 0.12(18) . . . . ? C16 N3 C20 C26 -179.25(11) . . . . ? N3 C20 C26 C25 165.67(10) . . . . ? C19 C20 C26 C25 -13.67(16) . . . . ? C20 C26 C25 C27 47.57(13) . . . . ? C20 C26 C25 C24 -73.17(12) . . . . ? C27 C25 C24 C23 -17.91(17) . . . . ? C26 C25 C24 C23 101.02(15) . . . . ? C25 C24 C23 C22 1.1(2) . . . . ? C25 C24 C23 C28 -179.25(14) . . . . ? C24 C25 C27 C29 -134.19(13) . . . . ? C26 C25 C27 C29 105.33(14) . . . . ? C24 C25 C27 C21 49.46(13) . . . . ? C26 C25 C27 C21 -71.02(12) . . . . ? C29 C27 C21 N4 -1.32(17) . . . . ? C25 C27 C21 N4 175.10(10) . . . . ? C29 C27 C21 C19 -122.81(12) . . . . ? C25 C27 C21 C19 53.60(12) . . . . ? C29 C27 C21 C22 119.25(13) . . . . ? C25 C27 C21 C22 -64.33(12) . . . . ? N3 C20 C19 C18 -1.45(16) . . . . ? C26 C20 C19 C18 177.87(11) . . . . ? N3 C20 C19 C21 179.03(10) . . . . ? C26 C20 C19 C21 -1.65(17) . . . . ? N4 C21 C19 C20 -144.02(11) . . . . ? C27 C21 C19 C20 -17.48(14) . . . . ? C22 C21 C19 C20 99.79(12) . . . . ? N4 C21 C19 C18 36.47(14) . . . . ? C27 C21 C19 C18 163.02(11) . . . . ? C22 C21 C19 C18 -79.71(13) . . . . ? O2 C16 C17 C18 179.85(12) . . . . ? N3 C16 C17 C18 -0.70(17) . . . . ? C16 C17 C18 C19 -0.63(19) . . . . ? C20 C19 C18 C17 1.72(18) . . . . ? C21 C19 C18 C17 -178.75(11) . . . . ? C24 C23 C22 C21 -15.89(18) . . . . ? C28 C23 C22 C21 164.46(12) . . . . ? N4 C21 C22 C23 172.15(10) . . . . ? C27 C21 C22 C23 45.97(13) . . . . ? C19 C21 C22 C23 -71.09(12) . . . . ? C25 C27 C29 C30 2.6(2) . . . . ? C21 C27 C29 C30 178.46(13) . . . . ? C1S C2S C3S C4S 178.77(13) . . . . ? C2S C3S C4S C5S -178.43(14) . . . . ? C3S C4S C5S C6S -177.52(16) . . . . ? _diffrn_measured_fraction_theta_max 0.987 _diffrn_reflns_theta_full 30.28 _diffrn_measured_fraction_theta_full 0.987 _refine_diff_density_max 0.510 _refine_diff_density_min -0.417 _refine_diff_density_rms 0.054 _database_code_depnum_ccdc_archive 'CCDC 958408' ####################################################################### # # Cambridge Crystallographic Data Centre # CCDC # ####################################################################### # # This CIF contains data from an original supplementary publication # deposited with the CCDC, and may include chemical, crystal, # experimental, refinement, atomic coordinates, # anisotropic displacement parameters and molecular geometry data, # as required by the journal to which it was submitted. # # This CIF is provided on the understanding that it is used for bona # fide research purposes only. It may contain copyright material # of the CCDC or of third parties, and may not be copied or further # disseminated in any form, whether machine-readable or not, # except for the purpose of generating routine backup copies # on your local computer system. # # For further information on the CCDC, data deposition and # data retrieval see: # www.ccdc.cam.ac.uk # # Bona fide researchers may freely download Mercury and enCIFer # from this site to visualise CIF-encoded structures and # to carry out CIF format checking respectively. # data_cd211134.CIF _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common 'Hup A Form s3' _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C15.25 H18.75 N2.25 O1.5' _chemical_formula_weight 257.58 _chemical_absolute_configuration unk 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 orthorhombic _symmetry_space_group_name_H-M P21212 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, z' 'x+1/2, -y+1/2, -z' '-x+1/2, y+1/2, -z' _cell_length_a 12.100(2) _cell_length_b 29.760(6) _cell_length_c 7.7000(15) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 2772.7(10) _cell_formula_units_Z 8 _cell_measurement_temperature 273(2) _cell_measurement_reflns_used 6169 _cell_measurement_theta_min 4.50 _cell_measurement_theta_max 54.87 _exptl_crystal_description ? _exptl_crystal_colour ? _exptl_crystal_size_max 0.25 _exptl_crystal_size_mid 0.22 _exptl_crystal_size_min 0.20 _exptl_crystal_density_meas 1.30 _exptl_crystal_density_diffrn 1.234 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1104 _exptl_absorpt_coefficient_mu 0.081 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.6526 _exptl_absorpt_correction_T_max 0.7456 _exptl_absorpt_process_details sadabs _exptl_special_details ; ? ; _diffrn_ambient_temperature 273(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 'Bruker APEX-II CCD' _diffrn_measurement_method '\f and \w scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 15260 _diffrn_reflns_av_R_equivalents 0.0378 _diffrn_reflns_av_sigmaI/netI 0.0505 _diffrn_reflns_limit_h_min -14 _diffrn_reflns_limit_h_max 14 _diffrn_reflns_limit_k_min -25 _diffrn_reflns_limit_k_max 36 _diffrn_reflns_limit_l_min -9 _diffrn_reflns_limit_l_max 9 _diffrn_reflns_theta_min 1.82 _diffrn_reflns_theta_max 26.00 _reflns_number_total 5431 _reflns_number_gt 3827 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker APEX2' _computing_cell_refinement 'Bruker SAINT' _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^)+(0.1000P)^2^+0.0000P] 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 0.0043(5) _refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^ _refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881' _refine_ls_abs_structure_Flack 2(2) _refine_ls_number_reflns 5431 _refine_ls_number_parameters 344 _refine_ls_number_restraints 3 _refine_ls_R_factor_all 0.0821 _refine_ls_R_factor_gt 0.0560 _refine_ls_wR_factor_ref 0.1681 _refine_ls_wR_factor_gt 0.1505 _refine_ls_goodness_of_fit_ref 1.023 _refine_ls_restrained_S_all 1.023 _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 N1 N 0.8027(2) 0.16127(7) 0.4714(3) 0.0404(5) Uani 1 1 d D . . N2 N 0.9974(2) 0.28965(10) 0.6468(3) 0.0561(7) Uani 1 1 d D . . N3 N 0.74731(19) 1.05643(7) 0.9727(3) 0.0424(6) Uani 1 1 d . . . H3A H 0.7673 1.0739 0.8861 0.051 Uiso 1 1 calc R . . N4 N 0.5628(2) 0.92589(9) 1.1434(4) 0.0647(8) Uani 1 1 d . . . H4A H 0.5698 0.9036 1.2218 0.078 Uiso 1 1 d R . . H4B H 0.4996 0.9418 1.1378 0.078 Uiso 1 1 d R . . O1 O 0.7743(2) 0.10290(6) 0.6560(3) 0.0584(6) Uani 1 1 d . . . O2 O 0.76670(19) 1.11594(6) 1.1541(3) 0.0595(6) Uani 1 1 d . . . O1S O 0.0385(6) 0.0332(2) 0.4084(11) 0.241(3) Uiso 1 1 d . . . C1 C 0.8012(2) 0.14291(9) 0.6357(4) 0.0423(6) Uani 1 1 d . . . C2 C 0.8304(2) 0.17344(9) 0.7715(4) 0.0437(7) Uani 1 1 d . . . H2 H 0.8272 0.1638 0.8890 0.052 Uiso 1 1 calc R . . C3 C 0.8624(2) 0.21557(9) 0.7347(4) 0.0422(7) Uani 1 1 d . . . H3 H 0.8830 0.2348 0.8277 0.051 Uiso 1 1 calc R . . C4 C 0.8665(2) 0.23247(9) 0.5638(4) 0.0389(6) Uani 1 1 d . . . C5 C 0.8335(2) 0.20428(8) 0.4336(4) 0.0374(6) Uani 1 1 d . . . C11 C 0.8278(3) 0.21750(8) 0.2460(4) 0.0438(7) Uani 1 1 d . . . H6A H 0.7575 0.2068 0.1951 0.053 Uiso 1 1 calc R . . H6B H 0.8894 0.2033 0.1815 0.053 Uiso 1 1 calc R . . C10 C 0.8353(2) 0.26934(9) 0.2283(4) 0.0434(7) Uani 1 1 d . . . H7 H 0.8488 0.2773 0.1039 0.052 Uiso 1 1 calc R . . C12 C 0.9332(2) 0.28367(9) 0.3352(4) 0.0425(7) Uani 1 1 d . . . C6 C 0.9059(2) 0.28024(9) 0.5260(4) 0.0427(7) Uani 1 1 d . . . C7 C 0.8130(3) 0.31310(9) 0.5689(4) 0.0494(7) Uani 1 1 d . . . H10A H 0.7835 0.3060 0.6857 0.059 Uiso 1 1 calc R . . H10B H 0.8436 0.3439 0.5727 0.059 Uiso 1 1 calc R . . C8 C 0.7202(3) 0.31167(9) 0.4399(4) 0.0505(8) Uani 1 1 d . . . C9 C 0.7314(3) 0.29166(9) 0.2882(4) 0.0477(7) Uani 1 1 d . . . H12 H 0.6696 0.2914 0.2122 0.057 Uiso 1 1 calc R . . C13 C 0.6155(3) 0.33431(12) 0.4968(5) 0.0695(10) Uani 1 1 d . . . H13A H 0.5603 0.3321 0.4042 0.104 Uiso 1 1 calc R . . H13B H 0.6305 0.3660 0.5215 0.104 Uiso 1 1 calc R . . H13C H 0.5875 0.3196 0.6018 0.104 Uiso 1 1 calc R . . C14 C 1.0298(3) 0.29584(11) 0.2730(4) 0.0613(9) Uani 1 1 d . . . H14 H 1.0847 0.3035 0.3560 0.074 Uiso 1 1 calc R . . C15 C 1.0628(4) 0.29899(16) 0.0875(5) 0.0948(14) Uani 1 1 d . . . H15A H 1.1004 0.2712 0.0528 0.142 Uiso 1 1 calc R . . H15B H 1.1130 0.3245 0.0719 0.142 Uiso 1 1 calc R . . H15C H 0.9969 0.3033 0.0154 0.142 Uiso 1 1 calc R . . C16 C 0.7450(2) 1.07508(9) 1.1362(4) 0.0431(6) Uani 1 1 d . . . C17 C 0.7208(2) 1.04472(9) 1.2711(4) 0.0473(7) Uani 1 1 d . . . H17 H 0.7247 1.0544 1.3885 0.057 Uiso 1 1 calc R . . C18 C 0.6919(2) 1.00151(10) 1.2344(4) 0.0458(7) Uani 1 1 d . . . H18 H 0.6722 0.9821 1.3275 0.055 Uiso 1 1 calc R . . C19 C 0.6902(2) 0.98445(8) 1.0644(3) 0.0374(6) Uani 1 1 d . . . C20 C 0.7212(2) 1.01301(8) 0.9343(3) 0.0382(6) Uani 1 1 d . . . C26 C 0.7309(3) 0.99971(9) 0.7477(4) 0.0480(7) Uani 1 1 d . . . H21A H 0.8012 1.0112 0.6991 0.058 Uiso 1 1 calc R . . H21B H 0.6692 1.0129 0.6804 0.058 Uiso 1 1 calc R . . C25 C 0.7278(2) 0.94828(9) 0.7331(4) 0.0467(7) Uani 1 1 d . . . H22 H 0.7171 0.9399 0.6085 0.056 Uiso 1 1 calc R . . C27 C 0.6298(2) 0.93240(9) 0.8354(4) 0.0454(7) Uani 1 1 d . . . C21 C 0.6531(2) 0.93631(9) 1.0262(4) 0.0456(7) Uani 1 1 d . . . C22 C 0.7481(3) 0.90344(10) 1.0681(4) 0.0551(8) Uani 1 1 d . . . H25A H 0.7750 0.9096 1.1871 0.066 Uiso 1 1 calc R . . H25B H 0.7187 0.8724 1.0665 0.066 Uiso 1 1 calc R . . C23 C 0.8426(3) 0.90610(9) 0.9469(5) 0.0566(8) Uani 1 1 d . . . C24 C 0.8327(3) 0.92769(10) 0.7968(4) 0.0555(8) Uani 1 1 d . . . H27 H 0.8964 0.9302 0.7254 0.067 Uiso 1 1 calc R . . C28 C 0.9488(4) 0.88415(13) 1.0011(7) 0.0932(14) Uani 1 1 d . . . H28A H 1.0078 0.8929 0.9208 0.140 Uiso 1 1 calc R . . H28B H 0.9399 0.8514 0.9990 0.140 Uiso 1 1 calc R . . H28C H 0.9680 0.8938 1.1190 0.140 Uiso 1 1 calc R . . C29 C 0.5341(3) 0.91927(10) 0.7677(5) 0.0577(8) Uani 1 1 d . . . H29 H 0.4785 0.9103 0.8476 0.069 Uiso 1 1 calc R . . C30 C 0.5049(3) 0.91709(12) 0.5827(5) 0.0756(11) Uani 1 1 d . . . H30A H 0.5056 0.9474 0.5333 0.113 Uiso 1 1 calc R . . H30B H 0.4309 0.9041 0.5701 0.113 Uiso 1 1 calc R . . H30C H 0.5586 0.8983 0.5213 0.113 Uiso 1 1 calc R . . N1S N 0.0000 0.0000 0.3675(12) 0.151(3) Uiso 1 2 d S . . C1S C 0.0000 0.0000 0.1654(9) 0.097(2) Uani 1 2 d S . . H32A H 0.0764 0.0000 0.1229 0.145 Uiso 0.50 1 calc PR . . H32B H -0.0382 0.0269 0.1229 0.145 Uiso 0.50 1 calc PR . . H32C H -0.0381 -0.0269 0.1229 0.145 Uiso 0.50 1 calc PR . . H1 H 0.7849 0.1440 0.3850 0.058(9) Uiso 1 1 d RD . . H2A H 1.0467 0.2706 0.6350 0.095(16) Uiso 1 1 d RD . . H2B H 1.0279 0.3149 0.6334 0.076(12) Uiso 1 1 d RD . . 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 N1 0.0556(14) 0.0346(12) 0.0311(13) -0.0029(10) -0.0033(10) -0.0029(10) N2 0.0679(17) 0.0555(17) 0.0450(16) -0.0035(12) -0.0152(14) -0.0171(17) N3 0.0556(14) 0.0358(12) 0.0358(13) 0.0016(10) 0.0006(11) -0.0023(11) N4 0.0759(18) 0.0626(17) 0.0558(17) 0.0035(14) 0.0240(15) -0.0179(15) O1 0.0933(16) 0.0402(11) 0.0416(12) 0.0069(9) -0.0011(12) -0.0131(11) O2 0.0945(16) 0.0387(11) 0.0453(12) -0.0057(9) -0.0036(12) -0.0087(11) C1 0.0497(15) 0.0423(16) 0.0350(16) 0.0050(12) -0.0007(13) 0.0004(13) C2 0.0554(17) 0.0485(16) 0.0272(14) 0.0024(12) -0.0016(13) 0.0029(14) C3 0.0525(16) 0.0413(16) 0.0328(15) -0.0048(13) -0.0047(13) -0.0025(13) C4 0.0459(14) 0.0393(15) 0.0316(15) -0.0004(12) -0.0038(13) -0.0013(12) C5 0.0466(15) 0.0338(14) 0.0318(14) -0.0002(12) -0.0022(12) -0.0003(12) C11 0.0605(17) 0.0392(15) 0.0317(15) -0.0012(12) -0.0077(13) -0.0051(13) C10 0.0614(18) 0.0397(15) 0.0291(15) 0.0017(12) -0.0059(13) -0.0076(13) C12 0.0511(16) 0.0381(15) 0.0382(16) -0.0025(12) -0.0053(13) -0.0056(13) C6 0.0543(17) 0.0417(16) 0.0322(15) -0.0007(12) -0.0087(12) -0.0084(13) C7 0.0663(19) 0.0362(15) 0.0457(17) -0.0081(13) 0.0036(16) -0.0088(14) C8 0.0580(18) 0.0359(16) 0.058(2) 0.0043(14) -0.0022(16) -0.0027(13) C9 0.0579(18) 0.0368(15) 0.0483(18) 0.0063(13) -0.0099(14) -0.0037(14) C13 0.066(2) 0.061(2) 0.081(3) -0.0023(19) 0.0118(19) 0.0066(18) C14 0.065(2) 0.078(2) 0.0412(18) -0.0071(16) -0.0029(16) -0.0194(18) C15 0.087(3) 0.143(4) 0.054(2) -0.015(2) 0.017(2) -0.040(3) C16 0.0545(16) 0.0401(16) 0.0348(16) -0.0041(12) -0.0008(14) 0.0028(13) C17 0.0606(18) 0.0474(17) 0.0339(16) -0.0038(13) 0.0048(14) -0.0031(14) C18 0.0541(16) 0.0487(16) 0.0345(16) 0.0029(13) 0.0111(14) 0.0015(13) C19 0.0447(14) 0.0365(14) 0.0309(15) -0.0008(11) 0.0007(13) 0.0030(12) C20 0.0485(15) 0.0339(14) 0.0321(15) -0.0003(11) -0.0003(13) 0.0022(12) C26 0.0736(19) 0.0372(14) 0.0333(15) 0.0012(12) 0.0011(15) -0.0014(14) C25 0.0696(19) 0.0385(15) 0.0321(15) -0.0051(12) 0.0041(14) 0.0011(14) C27 0.0556(17) 0.0328(15) 0.0479(18) -0.0010(13) -0.0010(14) 0.0008(13) C21 0.0596(18) 0.0379(15) 0.0394(17) 0.0076(12) 0.0039(13) -0.0015(13) C22 0.077(2) 0.0407(16) 0.0475(18) 0.0036(14) -0.0074(17) 0.0001(15) C23 0.065(2) 0.0393(17) 0.065(2) -0.0070(16) 0.0007(18) 0.0128(15) C24 0.0605(19) 0.0474(18) 0.059(2) -0.0121(16) 0.0115(16) 0.0005(15) C28 0.090(3) 0.076(3) 0.114(4) -0.007(2) -0.016(3) 0.029(2) C29 0.0594(19) 0.0559(19) 0.058(2) -0.0080(16) -0.0009(17) 0.0059(16) C30 0.073(2) 0.080(2) 0.073(3) -0.010(2) -0.024(2) 0.008(2) C1S 0.067(3) 0.095(4) 0.129(6) 0.000 0.000 -0.001(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 N1 C5 1.365(3) . ? N1 C1 1.378(3) . ? N1 H1 0.8676 . ? N2 C6 1.473(4) . ? N2 H2A 0.8280 . ? N2 H2B 0.8437 . ? N3 C20 1.363(3) . ? N3 C16 1.376(3) . ? N3 H3A 0.8800 . ? N4 C21 1.451(4) . ? N4 H4A 0.9001 . ? N4 H4B 0.9000 . ? O1 C1 1.244(3) . ? O2 C16 1.252(3) . ? O1S N1S 1.136(7) . ? C1 C2 1.430(4) . ? C2 C3 1.342(4) . ? C2 H2 0.9500 . ? C3 C4 1.410(4) . ? C3 H3 0.9500 . ? C4 C5 1.367(4) . ? C4 C6 1.528(4) . ? C5 C11 1.499(4) . ? C11 C10 1.551(4) . ? C11 H6A 0.9900 . ? C11 H6B 0.9900 . ? C10 C9 1.494(4) . ? C10 C12 1.504(4) . ? C10 H7 1.0000 . ? C12 C14 1.314(4) . ? C12 C6 1.509(4) . ? C6 C7 1.526(4) . ? C7 C8 1.500(4) . ? C7 H10A 0.9900 . ? C7 H10B 0.9900 . ? C8 C9 1.318(4) . ? C8 C13 1.500(5) . ? C9 H12 0.9500 . ? C13 H13A 0.9800 . ? C13 H13B 0.9800 . ? C13 H13C 0.9800 . ? C14 C15 1.486(5) . ? C14 H14 0.9500 . ? C15 H15A 0.9800 . ? C15 H15B 0.9800 . ? C15 H15C 0.9800 . ? C16 C17 1.407(4) . ? C17 C18 1.362(4) . ? C17 H17 0.9500 . ? C18 C19 1.405(4) . ? C18 H18 0.9500 . ? C19 C20 1.366(4) . ? C19 C21 1.530(4) . ? C20 C26 1.495(4) . ? C26 C25 1.535(4) . ? C26 H21A 0.9900 . ? C26 H21B 0.9900 . ? C25 C24 1.493(4) . ? C25 C27 1.499(4) . ? C25 H22 1.0000 . ? C27 C29 1.329(4) . ? C27 C21 1.501(4) . ? C21 C22 1.543(4) . ? C22 C23 1.477(5) . ? C22 H25A 0.9900 . ? C22 H25B 0.9900 . ? C23 C24 1.328(5) . ? C23 C28 1.501(5) . ? C24 H27 0.9500 . ? C28 H28A 0.9800 . ? C28 H28B 0.9800 . ? C28 H28C 0.9800 . ? C29 C30 1.469(5) . ? C29 H29 0.9500 . ? C30 H30A 0.9800 . ? C30 H30B 0.9800 . ? C30 H30C 0.9800 . ? N1S O1S 1.136(7) 2 ? N1S C1S 1.557(10) . ? C1S H32A 0.9800 . ? C1S H32B 0.9800 . ? C1S H32C 0.9800 . ? 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 C5 N1 C1 124.9(2) . . ? C5 N1 H1 117.4 . . ? C1 N1 H1 117.7 . . ? C6 N2 H2A 110.0 . . ? C6 N2 H2B 114.9 . . ? H2A N2 H2B 106.5 . . ? C20 N3 C16 125.2(2) . . ? C20 N3 H3A 117.4 . . ? C16 N3 H3A 117.4 . . ? C21 N4 H4A 120.2 . . ? C21 N4 H4B 119.8 . . ? H4A N4 H4B 120.0 . . ? O1 C1 N1 119.9(2) . . ? O1 C1 C2 125.5(3) . . ? N1 C1 C2 114.6(2) . . ? C3 C2 C1 120.7(3) . . ? C3 C2 H2 119.6 . . ? C1 C2 H2 119.6 . . ? C2 C3 C4 122.7(2) . . ? C2 C3 H3 118.6 . . ? C4 C3 H3 118.6 . . ? C5 C4 C3 117.1(2) . . ? C5 C4 C6 121.5(2) . . ? C3 C4 C6 121.4(2) . . ? N1 C5 C4 119.9(2) . . ? N1 C5 C11 116.1(2) . . ? C4 C5 C11 124.0(2) . . ? C5 C11 C10 110.1(2) . . ? C5 C11 H6A 109.6 . . ? C10 C11 H6A 109.6 . . ? C5 C11 H6B 109.6 . . ? C10 C11 H6B 109.6 . . ? H6A C11 H6B 108.2 . . ? C9 C10 C12 111.6(2) . . ? C9 C10 C11 111.5(2) . . ? C12 C10 C11 106.2(2) . . ? C9 C10 H7 109.2 . . ? C12 C10 H7 109.2 . . ? C11 C10 H7 109.2 . . ? C14 C12 C10 125.4(3) . . ? C14 C12 C6 124.6(3) . . ? C10 C12 C6 110.0(2) . . ? N2 C6 C12 115.9(2) . . ? N2 C6 C7 107.2(2) . . ? C12 C6 C7 109.2(2) . . ? N2 C6 C4 106.9(2) . . ? C12 C6 C4 108.5(2) . . ? C7 C6 C4 109.0(2) . . ? C8 C7 C6 112.9(2) . . ? C8 C7 H10A 109.0 . . ? C6 C7 H10A 109.0 . . ? C8 C7 H10B 109.0 . . ? C6 C7 H10B 109.0 . . ? H10A C7 H10B 107.8 . . ? C9 C8 C13 123.3(3) . . ? C9 C8 C7 121.5(3) . . ? C13 C8 C7 115.2(3) . . ? C8 C9 C10 124.1(3) . . ? C8 C9 H12 117.9 . . ? C10 C9 H12 117.9 . . ? C8 C13 H13A 109.5 . . ? C8 C13 H13B 109.5 . . ? H13A C13 H13B 109.5 . . ? C8 C13 H13C 109.5 . . ? H13A C13 H13C 109.5 . . ? H13B C13 H13C 109.5 . . ? C12 C14 C15 127.4(3) . . ? C12 C14 H14 116.3 . . ? C15 C14 H14 116.3 . . ? C14 C15 H15A 109.5 . . ? C14 C15 H15B 109.5 . . ? H15A C15 H15B 109.5 . . ? C14 C15 H15C 109.5 . . ? H15A C15 H15C 109.5 . . ? H15B C15 H15C 109.5 . . ? O2 C16 N3 119.2(2) . . ? O2 C16 C17 125.9(2) . . ? N3 C16 C17 114.9(2) . . ? C18 C17 C16 120.4(3) . . ? C18 C17 H17 119.8 . . ? C16 C17 H17 119.8 . . ? C17 C18 C19 122.6(3) . . ? C17 C18 H18 118.7 . . ? C19 C18 H18 118.7 . . ? C20 C19 C18 117.0(2) . . ? C20 C19 C21 121.5(2) . . ? C18 C19 C21 121.5(2) . . ? N3 C20 C19 119.7(2) . . ? N3 C20 C26 116.2(2) . . ? C19 C20 C26 124.1(2) . . ? C20 C26 C25 109.4(2) . . ? C20 C26 H21A 109.8 . . ? C25 C26 H21A 109.8 . . ? C20 C26 H21B 109.8 . . ? C25 C26 H21B 109.8 . . ? H21A C26 H21B 108.2 . . ? C24 C25 C27 111.7(2) . . ? C24 C25 C26 111.4(3) . . ? C27 C25 C26 107.2(2) . . ? C24 C25 H22 108.8 . . ? C27 C25 H22 108.8 . . ? C26 C25 H22 108.8 . . ? C29 C27 C25 125.1(3) . . ? C29 C27 C21 124.8(3) . . ? C25 C27 C21 110.0(3) . . ? N4 C21 C27 116.8(3) . . ? N4 C21 C19 107.6(2) . . ? C27 C21 C19 108.4(2) . . ? N4 C21 C22 107.2(2) . . ? C27 C21 C22 107.2(2) . . ? C19 C21 C22 109.6(2) . . ? C23 C22 C21 114.2(3) . . ? C23 C22 H25A 108.7 . . ? C21 C22 H25A 108.7 . . ? C23 C22 H25B 108.7 . . ? C21 C22 H25B 108.7 . . ? H25A C22 H25B 107.6 . . ? C24 C23 C22 120.4(3) . . ? C24 C23 C28 122.0(4) . . ? C22 C23 C28 117.6(3) . . ? C23 C24 C25 124.1(3) . . ? C23 C24 H27 117.9 . . ? C25 C24 H27 117.9 . . ? C23 C28 H28A 109.5 . . ? C23 C28 H28B 109.5 . . ? H28A C28 H28B 109.5 . . ? C23 C28 H28C 109.5 . . ? H28A C28 H28C 109.5 . . ? H28B C28 H28C 109.5 . . ? C27 C29 C30 127.1(3) . . ? C27 C29 H29 116.5 . . ? C30 C29 H29 116.5 . . ? C29 C30 H30A 109.5 . . ? C29 C30 H30B 109.5 . . ? H30A C30 H30B 109.5 . . ? C29 C30 H30C 109.5 . . ? H30A C30 H30C 109.5 . . ? H30B C30 H30C 109.5 . . ? O1S N1S O1S 147.9(13) . 2 ? O1S N1S C1S 106.1(7) . . ? O1S N1S C1S 106.1(7) 2 . ? N1S C1S H32A 109.5 . . ? N1S C1S H32B 109.5 . . ? H32A C1S H32B 109.5 . . ? N1S C1S H32C 109.5 . . ? H32A C1S H32C 109.5 . . ? H32B C1S H32C 109.5 . . ? 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 C5 N1 C1 O1 -178.2(3) . . . . ? C5 N1 C1 C2 2.7(4) . . . . ? O1 C1 C2 C3 177.4(3) . . . . ? N1 C1 C2 C3 -3.6(4) . . . . ? C1 C2 C3 C4 1.5(4) . . . . ? C2 C3 C4 C5 1.6(4) . . . . ? C2 C3 C4 C6 -178.5(3) . . . . ? C1 N1 C5 C4 0.3(4) . . . . ? C1 N1 C5 C11 -179.3(3) . . . . ? C3 C4 C5 N1 -2.5(4) . . . . ? C6 C4 C5 N1 177.6(2) . . . . ? C3 C4 C5 C11 177.1(3) . . . . ? C6 C4 C5 C11 -2.8(4) . . . . ? N1 C5 C11 C10 165.4(2) . . . . ? C4 C5 C11 C10 -14.2(4) . . . . ? C5 C11 C10 C9 -72.2(3) . . . . ? C5 C11 C10 C12 49.5(3) . . . . ? C9 C10 C12 C14 -133.8(3) . . . . ? C11 C10 C12 C14 104.5(3) . . . . ? C9 C10 C12 C6 48.5(3) . . . . ? C11 C10 C12 C6 -73.2(3) . . . . ? C14 C12 C6 N2 -2.6(5) . . . . ? C10 C12 C6 N2 175.1(2) . . . . ? C14 C12 C6 C7 118.5(3) . . . . ? C10 C12 C6 C7 -63.8(3) . . . . ? C14 C12 C6 C4 -122.9(3) . . . . ? C10 C12 C6 C4 54.8(3) . . . . ? C5 C4 C6 N2 -142.5(3) . . . . ? C3 C4 C6 N2 37.7(4) . . . . ? C5 C4 C6 C12 -16.8(4) . . . . ? C3 C4 C6 C12 163.4(3) . . . . ? C5 C4 C6 C7 102.0(3) . . . . ? C3 C4 C6 C7 -77.9(3) . . . . ? N2 C6 C7 C8 172.0(2) . . . . ? C12 C6 C7 C8 45.7(3) . . . . ? C4 C6 C7 C8 -72.6(3) . . . . ? C6 C7 C8 C9 -14.2(4) . . . . ? C6 C7 C8 C13 165.6(3) . . . . ? C13 C8 C9 C10 179.3(3) . . . . ? C7 C8 C9 C10 -0.9(4) . . . . ? C12 C10 C9 C8 -16.6(4) . . . . ? C11 C10 C9 C8 102.0(3) . . . . ? C10 C12 C14 C15 1.3(6) . . . . ? C6 C12 C14 C15 178.6(4) . . . . ? C20 N3 C16 O2 -177.3(3) . . . . ? C20 N3 C16 C17 4.7(4) . . . . ? O2 C16 C17 C18 176.1(3) . . . . ? N3 C16 C17 C18 -6.0(4) . . . . ? C16 C17 C18 C19 3.3(4) . . . . ? C17 C18 C19 C20 1.3(4) . . . . ? C17 C18 C19 C21 -177.6(3) . . . . ? C16 N3 C20 C19 -0.3(4) . . . . ? C16 N3 C20 C26 -179.2(3) . . . . ? C18 C19 C20 N3 -2.8(4) . . . . ? C21 C19 C20 N3 176.1(2) . . . . ? C18 C19 C20 C26 176.1(3) . . . . ? C21 C19 C20 C26 -5.1(4) . . . . ? N3 C20 C26 C25 165.8(2) . . . . ? C19 C20 C26 C25 -13.1(4) . . . . ? C20 C26 C25 C24 -72.7(3) . . . . ? C20 C26 C25 C27 49.8(3) . . . . ? C24 C25 C27 C29 -134.9(3) . . . . ? C26 C25 C27 C29 102.8(3) . . . . ? C24 C25 C27 C21 48.7(3) . . . . ? C26 C25 C27 C21 -73.5(3) . . . . ? C29 C27 C21 N4 -1.5(4) . . . . ? C25 C27 C21 N4 174.8(2) . . . . ? C29 C27 C21 C19 -123.1(3) . . . . ? C25 C27 C21 C19 53.2(3) . . . . ? C29 C27 C21 C22 118.6(3) . . . . ? C25 C27 C21 C22 -65.0(3) . . . . ? C20 C19 C21 N4 -141.7(3) . . . . ? C18 C19 C21 N4 37.1(4) . . . . ? C20 C19 C21 C27 -14.6(4) . . . . ? C18 C19 C21 C27 164.2(3) . . . . ? C20 C19 C21 C22 102.1(3) . . . . ? C18 C19 C21 C22 -79.1(3) . . . . ? N4 C21 C22 C23 173.5(3) . . . . ? C27 C21 C22 C23 47.4(3) . . . . ? C19 C21 C22 C23 -70.1(3) . . . . ? C21 C22 C23 C24 -14.0(4) . . . . ? C21 C22 C23 C28 165.3(3) . . . . ? C22 C23 C24 C25 -3.6(5) . . . . ? C28 C23 C24 C25 177.1(3) . . . . ? C27 C25 C24 C23 -13.9(4) . . . . ? C26 C25 C24 C23 106.0(3) . . . . ? C25 C27 C29 C30 0.7(5) . . . . ? C21 C27 C29 C30 176.5(3) . . . . ? 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 N1 H1 O2 0.87 1.98 2.824(3) 165.3 1_544 N3 H3A O1 0.88 1.97 2.822(3) 162.1 1_565 _diffrn_measured_fraction_theta_max 0.996 _diffrn_reflns_theta_full 26.00 _diffrn_measured_fraction_theta_full 0.996 _refine_diff_density_max 0.663 _refine_diff_density_min -0.271 _refine_diff_density_rms 0.045 _database_code_depnum_ccdc_archive 'CCDC 958409' ####################################################################### # # Cambridge Crystallographic Data Centre # CCDC # ####################################################################### # # This CIF contains data from an original supplementary publication # deposited with the CCDC, and may include chemical, crystal, # experimental, refinement, atomic coordinates, # anisotropic displacement parameters and molecular geometry data, # as required by the journal to which it was submitted. # # This CIF is provided on the understanding that it is used for bona # fide research purposes only. It may contain copyright material # of the CCDC or of third parties, and may not be copied or further # disseminated in any form, whether machine-readable or not, # except for the purpose of generating routine backup copies # on your local computer system. # # For further information on the CCDC, data deposition and # data retrieval see: # www.ccdc.cam.ac.uk # # Bona fide researchers may freely download Mercury and enCIFer # from this site to visualise CIF-encoded structures and # to carry out CIF format checking respectively. # data_S4.CIF _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common 'Hup A Form S2' _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C19 H26 N2 O2' _chemical_formula_weight 314.42 _chemical_absolute_configuration unk 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 monoclinic _symmetry_space_group_name_H-M C2 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y, -z' 'x+1/2, y+1/2, z' '-x+1/2, y+1/2, -z' _cell_length_a 19.9216(4) _cell_length_b 7.47330(10) _cell_length_c 15.2146(3) _cell_angle_alpha 90.00 _cell_angle_beta 130.2740(10) _cell_angle_gamma 90.00 _cell_volume 1728.22(5) _cell_formula_units_Z 4 _cell_measurement_temperature 296(2) _cell_measurement_reflns_used 3384 _cell_measurement_theta_min 1.75 _cell_measurement_theta_max 27.51 _exptl_crystal_description chunk _exptl_crystal_colour colorless _exptl_crystal_size_max 0.43 _exptl_crystal_size_mid 0.32 _exptl_crystal_size_min 0.25 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.208 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 680 _exptl_absorpt_coefficient_mu 0.078 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.970 _exptl_absorpt_correction_T_max 0.981 _exptl_absorpt_process_details sadabs _exptl_special_details ; ? ; _diffrn_ambient_temperature 296(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 'Bruker APEX-II CCD' _diffrn_measurement_method '\f and \w scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 14752 _diffrn_reflns_av_R_equivalents 0.0196 _diffrn_reflns_av_sigmaI/netI 0.0187 _diffrn_reflns_limit_h_min -25 _diffrn_reflns_limit_h_max 25 _diffrn_reflns_limit_k_min -9 _diffrn_reflns_limit_k_max 9 _diffrn_reflns_limit_l_min -19 _diffrn_reflns_limit_l_max 19 _diffrn_reflns_theta_min 1.75 _diffrn_reflns_theta_max 27.51 _reflns_number_total 3884 _reflns_number_gt 3803 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker APEX2' _computing_cell_refinement 'Bruker SAINT' _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^)+(0.0653P)^2^+0.7311P] 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 0.0043(5) _refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^ _refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881' _refine_ls_abs_structure_Flack 0.6(10) _refine_ls_number_reflns 3884 _refine_ls_number_parameters 218 _refine_ls_number_restraints 4 _refine_ls_R_factor_all 0.0369 _refine_ls_R_factor_gt 0.0361 _refine_ls_wR_factor_ref 0.1020 _refine_ls_wR_factor_gt 0.1011 _refine_ls_goodness_of_fit_ref 1.053 _refine_ls_restrained_S_all 1.053 _refine_ls_shift/su_max 0.000 _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 N1 N 0.29111(7) 0.51579(15) 0.93319(9) 0.0162(2) Uani 1 1 d . . . H1' H 0.2753 0.4242 0.9502 0.019 Uiso 1 1 calc R . . O1S O 0.38483(9) 0.4814(2) 0.41652(12) 0.0452(3) Uani 1 1 d . . . O1 O 0.25347(7) 0.69534(13) 1.01674(9) 0.0222(2) Uani 1 1 d . . . N2 N 0.45451(9) 0.73569(18) 0.83089(12) 0.0265(3) Uani 1 1 d D . . H5 H 0.5005(9) 0.719(3) 0.9020(9) 0.040 Uiso 1 1 d D . . H6 H 0.4700(13) 0.729(3) 0.7905(15) 0.040 Uiso 1 1 d D . . C15 C 0.51637(10) 0.1660(2) 0.83599(14) 0.0285(3) Uani 1 1 d . . . H4 H 0.4898 0.0881 0.8561 0.043 Uiso 1 1 calc R . . H3 H 0.5792 0.1576 0.8935 0.043 Uiso 1 1 calc R . . H1 H 0.4980 0.1312 0.7625 0.043 Uiso 1 1 calc R . . C14 C 0.48814(9) 0.3559(2) 0.82945(12) 0.0229(3) Uani 1 1 d . . . H2 H 0.5291 0.4452 0.8525 0.027 Uiso 1 1 calc R . . C12 C 0.41051(9) 0.40794(18) 0.79403(11) 0.0179(3) Uani 1 1 d . . . C10 C 0.33539(9) 0.28650(17) 0.75626(11) 0.0174(2) Uani 1 1 d . . . H15 H 0.3496 0.1636 0.7508 0.021 Uiso 1 1 calc R . . C11 C 0.32575(9) 0.29424(17) 0.84902(11) 0.0172(2) Uani 1 1 d . . . H17 H 0.2723 0.2332 0.8213 0.021 Uiso 1 1 calc R . . H16 H 0.3752 0.2339 0.9182 0.021 Uiso 1 1 calc R . . C5 C 0.32253(8) 0.48621(17) 0.87650(11) 0.0160(2) Uani 1 1 d . . . C1 C 0.28306(8) 0.68210(17) 0.96485(11) 0.0166(2) Uani 1 1 d . . . C6 C 0.38465(9) 0.60356(18) 0.78462(12) 0.0191(3) Uani 1 1 d . . . C4 C 0.34915(8) 0.62731(17) 0.84838(11) 0.0178(3) Uani 1 1 d . . . C3 C 0.34077(9) 0.80222(18) 0.87727(12) 0.0207(3) Uani 1 1 d . . . H7 H 0.3570 0.9003 0.8570 0.025 Uiso 1 1 calc R . . C2 C 0.30964(9) 0.83006(17) 0.93376(12) 0.0203(3) Uani 1 1 d . . . H8 H 0.3056 0.9459 0.9523 0.024 Uiso 1 1 calc R . . C7 C 0.31086(10) 0.64434(19) 0.65531(12) 0.0228(3) Uani 1 1 d . . . H9 H 0.2844 0.7587 0.6475 0.027 Uiso 1 1 calc R . . H14 H 0.3365 0.6547 0.6189 0.027 Uiso 1 1 calc R . . C8 C 0.24013(9) 0.5040(2) 0.59334(11) 0.0219(3) Uani 1 1 d . . . C13 C 0.15698(11) 0.5547(3) 0.47488(13) 0.0327(4) Uani 1 1 d . . . H11 H 0.1699 0.5721 0.4246 0.049 Uiso 1 1 calc R . . H12 H 0.1338 0.6635 0.4796 0.049 Uiso 1 1 calc R . . H10 H 0.1144 0.4608 0.4451 0.049 Uiso 1 1 calc R . . C9 C 0.25130(9) 0.34342(19) 0.63996(12) 0.0199(3) Uani 1 1 d . . . H13 H 0.2049 0.2625 0.5987 0.024 Uiso 1 1 calc R . . C1S C 0.40208(12) 0.2196(3) 0.34049(17) 0.0432(4) Uani 1 1 d . . . H18 H 0.4607 0.1739 0.3969 0.065 Uiso 1 1 calc R . . H23 H 0.3821 0.1975 0.2647 0.065 Uiso 1 1 calc R . . H22 H 0.3636 0.1609 0.3488 0.065 Uiso 1 1 calc R . . C2S C 0.40179(11) 0.4226(3) 0.35818(15) 0.0395(4) Uani 1 1 d . . . C3S C 0.42295(13) 0.5390(3) 0.29959(17) 0.0459(5) Uani 1 1 d . . . H21 H 0.3759 0.5286 0.2170 0.055 Uiso 1 1 calc R . . H24 H 0.4764 0.4950 0.3174 0.055 Uiso 1 1 calc R . . C4S C 0.43531(14) 0.7330(3) 0.33208(19) 0.0476(5) Uani 1 1 d . . . H19 H 0.3872 0.7732 0.3271 0.071 Uiso 1 1 calc R . . H20 H 0.4372 0.8019 0.2804 0.071 Uiso 1 1 calc R . . H25 H 0.4895 0.7482 0.4095 0.071 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 N1 0.0214(5) 0.0146(5) 0.0171(5) 0.0005(4) 0.0144(4) -0.0005(4) O1S 0.0554(8) 0.0465(8) 0.0543(8) -0.0043(7) 0.0448(7) -0.0001(7) O1 0.0310(5) 0.0193(5) 0.0276(5) -0.0012(4) 0.0240(4) 0.0003(4) N2 0.0317(7) 0.0252(6) 0.0333(7) -0.0073(6) 0.0258(6) -0.0109(5) C15 0.0243(6) 0.0311(8) 0.0278(7) 0.0001(6) 0.0158(6) 0.0055(6) C14 0.0225(6) 0.0273(7) 0.0207(6) -0.0034(5) 0.0149(6) -0.0033(5) C12 0.0221(6) 0.0205(6) 0.0142(6) -0.0017(5) 0.0132(5) -0.0026(5) C10 0.0233(6) 0.0159(5) 0.0187(6) -0.0021(5) 0.0163(5) -0.0016(5) C11 0.0247(6) 0.0145(6) 0.0183(6) -0.0004(5) 0.0166(5) -0.0007(5) C5 0.0182(6) 0.0169(6) 0.0142(5) -0.0010(5) 0.0111(5) -0.0006(5) C1 0.0166(5) 0.0173(6) 0.0149(5) -0.0010(5) 0.0097(5) -0.0005(5) C6 0.0239(6) 0.0187(6) 0.0216(6) -0.0017(5) 0.0178(6) -0.0035(5) C4 0.0203(6) 0.0174(6) 0.0179(6) -0.0011(5) 0.0133(5) -0.0022(5) C3 0.0268(6) 0.0166(6) 0.0238(7) -0.0007(5) 0.0187(6) -0.0038(5) C2 0.0247(6) 0.0149(6) 0.0237(7) -0.0015(5) 0.0167(6) -0.0011(5) C7 0.0315(7) 0.0206(6) 0.0234(7) 0.0040(5) 0.0210(6) -0.0005(5) C8 0.0249(6) 0.0274(7) 0.0169(6) 0.0004(6) 0.0151(5) 0.0010(6) C13 0.0315(8) 0.0422(9) 0.0208(7) 0.0062(7) 0.0152(6) 0.0047(7) C9 0.0215(6) 0.0242(6) 0.0176(6) -0.0045(5) 0.0143(5) -0.0048(5) C1S 0.0332(9) 0.0538(12) 0.0358(9) -0.0022(9) 0.0193(8) 0.0034(8) C2S 0.0271(8) 0.0601(12) 0.0283(8) -0.0028(8) 0.0165(7) 0.0029(8) C3S 0.0379(9) 0.0665(14) 0.0341(9) 0.0004(10) 0.0236(8) 0.0009(9) C4S 0.0429(10) 0.0550(13) 0.0458(11) 0.0025(10) 0.0290(9) -0.0018(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 N1 C5 1.3720(15) . ? N1 C1 1.3793(16) . ? N1 H1' 0.8600 . ? O1S C2S 1.218(2) . ? O1 C1 1.2578(15) . ? N2 C6 1.4631(17) . ? N2 H5 0.862(9) . ? N2 H6 0.848(9) . ? C15 C14 1.506(2) . ? C15 H4 0.9600 . ? C15 H3 0.9600 . ? C15 H1 0.9600 . ? C14 C12 1.3249(19) . ? C14 H2 0.9300 . ? C12 C10 1.5105(17) . ? C12 C6 1.5258(19) . ? C10 C9 1.5119(19) . ? C10 C11 1.5436(17) . ? C10 H15 0.9800 . ? C11 C5 1.5072(17) . ? C11 H17 0.9700 . ? C11 H16 0.9700 . ? C5 C4 1.3673(18) . ? C1 C2 1.4319(18) . ? C6 C4 1.5362(17) . ? C6 C7 1.5444(19) . ? C4 C3 1.4229(18) . ? C3 C2 1.3622(18) . ? C3 H7 0.9300 . ? C2 H8 0.9300 . ? C7 C8 1.502(2) . ? C7 H9 0.9700 . ? C7 H14 0.9700 . ? C8 C9 1.337(2) . ? C8 C13 1.509(2) . ? C13 H11 0.9600 . ? C13 H12 0.9600 . ? C13 H10 0.9600 . ? C9 H13 0.9300 . ? C1S C2S 1.542(3) . ? C1S H18 0.9600 . ? C1S H23 0.9600 . ? C1S H22 0.9600 . ? C2S C3S 1.488(3) . ? C3S C4S 1.500(3) . ? C3S H21 0.9700 . ? C3S H24 0.9700 . ? C4S H19 0.9600 . ? C4S H20 0.9600 . ? C4S H25 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 C5 N1 C1 124.61(11) . . ? C5 N1 H1' 117.7 . . ? C1 N1 H1' 117.7 . . ? C6 N2 H5 114.6(16) . . ? C6 N2 H6 106.9(15) . . ? H5 N2 H6 108.2(18) . . ? C14 C15 H4 109.5 . . ? C14 C15 H3 109.5 . . ? H4 C15 H3 109.5 . . ? C14 C15 H1 109.5 . . ? H4 C15 H1 109.5 . . ? H3 C15 H1 109.5 . . ? C12 C14 C15 126.23(13) . . ? C12 C14 H2 116.9 . . ? C15 C14 H2 116.9 . . ? C14 C12 C10 125.97(13) . . ? C14 C12 C6 123.63(12) . . ? C10 C12 C6 110.40(11) . . ? C12 C10 C9 110.61(11) . . ? C12 C10 C11 107.93(11) . . ? C9 C10 C11 111.15(10) . . ? C12 C10 H15 109.0 . . ? C9 C10 H15 109.0 . . ? C11 C10 H15 109.0 . . ? C5 C11 C10 110.00(10) . . ? C5 C11 H17 109.7 . . ? C10 C11 H17 109.7 . . ? C5 C11 H16 109.7 . . ? C10 C11 H16 109.7 . . ? H17 C11 H16 108.2 . . ? C4 C5 N1 119.95(11) . . ? C4 C5 C11 123.54(11) . . ? N1 C5 C11 116.50(11) . . ? O1 C1 N1 119.84(11) . . ? O1 C1 C2 124.75(12) . . ? N1 C1 C2 115.41(11) . . ? N2 C6 C12 116.30(11) . . ? N2 C6 C4 107.53(11) . . ? C12 C6 C4 108.47(10) . . ? N2 C6 C7 107.81(11) . . ? C12 C6 C7 107.11(11) . . ? C4 C6 C7 109.51(11) . . ? C5 C4 C3 117.72(12) . . ? C5 C4 C6 122.58(12) . . ? C3 C4 C6 119.68(11) . . ? C2 C3 C4 121.83(12) . . ? C2 C3 H7 119.1 . . ? C4 C3 H7 119.1 . . ? C3 C2 C1 120.45(12) . . ? C3 C2 H8 119.8 . . ? C1 C2 H8 119.8 . . ? C8 C7 C6 113.32(11) . . ? C8 C7 H9 108.9 . . ? C6 C7 H9 108.9 . . ? C8 C7 H14 108.9 . . ? C6 C7 H14 108.9 . . ? H9 C7 H14 107.7 . . ? C9 C8 C7 121.78(12) . . ? C9 C8 C13 122.48(13) . . ? C7 C8 C13 115.73(13) . . ? C8 C13 H11 109.5 . . ? C8 C13 H12 109.5 . . ? H11 C13 H12 109.5 . . ? C8 C13 H10 109.5 . . ? H11 C13 H10 109.5 . . ? H12 C13 H10 109.5 . . ? C8 C9 C10 123.49(12) . . ? C8 C9 H13 118.3 . . ? C10 C9 H13 118.3 . . ? C2S C1S H18 109.5 . . ? C2S C1S H23 109.5 . . ? H18 C1S H23 109.5 . . ? C2S C1S H22 109.5 . . ? H18 C1S H22 109.5 . . ? H23 C1S H22 109.5 . . ? O1S C2S C3S 123.0(2) . . ? O1S C2S C1S 121.10(19) . . ? C3S C2S C1S 115.85(17) . . ? C2S C3S C4S 114.66(17) . . ? C2S C3S H21 108.6 . . ? C4S C3S H21 108.6 . . ? C2S C3S H24 108.6 . . ? C4S C3S H24 108.6 . . ? H21 C3S H24 107.6 . . ? C3S C4S H19 109.5 . . ? C3S C4S H20 109.5 . . ? H19 C4S H20 109.5 . . ? C3S C4S H25 109.5 . . ? H19 C4S H25 109.5 . . ? H20 C4S H25 109.5 . . ? 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 C15 C14 C12 C10 1.9(2) . . . . ? C15 C14 C12 C6 -177.28(13) . . . . ? C14 C12 C10 C9 -128.42(14) . . . . ? C6 C12 C10 C9 50.87(14) . . . . ? C14 C12 C10 C11 109.78(14) . . . . ? C6 C12 C10 C11 -70.92(13) . . . . ? C12 C10 C11 C5 50.11(14) . . . . ? C9 C10 C11 C5 -71.35(14) . . . . ? C1 N1 C5 C4 0.53(19) . . . . ? C1 N1 C5 C11 -179.70(11) . . . . ? C10 C11 C5 C4 -17.01(17) . . . . ? C10 C11 C5 N1 163.23(11) . . . . ? C5 N1 C1 O1 -179.98(12) . . . . ? C5 N1 C1 C2 0.44(18) . . . . ? C14 C12 C6 N2 -7.47(19) . . . . ? C10 C12 C6 N2 173.22(11) . . . . ? C14 C12 C6 C4 -128.75(13) . . . . ? C10 C12 C6 C4 51.93(14) . . . . ? C14 C12 C6 C7 113.13(14) . . . . ? C10 C12 C6 C7 -66.18(13) . . . . ? N1 C5 C4 C3 -1.58(19) . . . . ? C11 C5 C4 C3 178.67(12) . . . . ? N1 C5 C4 C6 -179.79(11) . . . . ? C11 C5 C4 C6 0.5(2) . . . . ? N2 C6 C4 C5 -143.80(13) . . . . ? C12 C6 C4 C5 -17.26(17) . . . . ? C7 C6 C4 C5 99.32(15) . . . . ? N2 C6 C4 C3 38.02(17) . . . . ? C12 C6 C4 C3 164.56(12) . . . . ? C7 C6 C4 C3 -78.86(15) . . . . ? C5 C4 C3 C2 1.7(2) . . . . ? C6 C4 C3 C2 -179.99(12) . . . . ? C4 C3 C2 C1 -0.8(2) . . . . ? O1 C1 C2 C3 -179.85(13) . . . . ? N1 C1 C2 C3 -0.29(18) . . . . ? N2 C6 C7 C8 172.38(11) . . . . ? C12 C6 C7 C8 46.52(14) . . . . ? C4 C6 C7 C8 -70.91(14) . . . . ? C6 C7 C8 C9 -14.35(18) . . . . ? C6 C7 C8 C13 166.79(12) . . . . ? C7 C8 C9 C10 -1.51(19) . . . . ? C13 C8 C9 C10 177.27(13) . . . . ? C12 C10 C9 C8 -16.80(17) . . . . ? C11 C10 C9 C8 103.08(14) . . . . ? O1S C2S C3S C4S 8.8(3) . . . . ? C1S C2S C3S C4S -171.39(17) . . . . ? _diffrn_measured_fraction_theta_max 0.999 _diffrn_reflns_theta_full 27.51 _diffrn_measured_fraction_theta_full 0.999 _refine_diff_density_max 0.420 _refine_diff_density_min -0.214 _refine_diff_density_rms 0.044 _database_code_depnum_ccdc_archive 'CCDC 958410'