# Electronic Supplementary Material (ESI) for Organic & Biomolecular Chemistry # This journal is © The Royal Society of Chemistry 2012 ####################################################################### # # 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_p _database_code_depnum_ccdc_archive 'CCDC 891147' #TrackingRef 'bxzhao.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C20 H21 N3 O2 S' _chemical_formula_weight 367.46 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' S S 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting ? _symmetry_space_group_name_H-M ? loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y, -z+1/2' 'x+1/2, y+1/2, z' '-x+1/2, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y, z-1/2' '-x+1/2, -y+1/2, -z' 'x+1/2, -y+1/2, z-1/2' _cell_length_a 26.280(10) _cell_length_b 10.188(4) _cell_length_c 16.786(6) _cell_angle_alpha 90.00 _cell_angle_beta 124.377(7) _cell_angle_gamma 90.00 _cell_volume 3709(2) _cell_formula_units_Z 8 _cell_measurement_temperature 298(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description ? _exptl_crystal_colour ? _exptl_crystal_size_max 0.20 _exptl_crystal_size_mid 0.15 _exptl_crystal_size_min 0.10 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.316 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1552 _exptl_absorpt_coefficient_mu 0.194 _exptl_absorpt_correction_type ? _exptl_absorpt_correction_T_min 0.9623 _exptl_absorpt_correction_T_max 0.9809 _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 298(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 ? _diffrn_measurement_method ? _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 8589 _diffrn_reflns_av_R_equivalents 0.0587 _diffrn_reflns_av_sigmaI/netI 0.0824 _diffrn_reflns_limit_h_min -19 _diffrn_reflns_limit_h_max 31 _diffrn_reflns_limit_k_min -12 _diffrn_reflns_limit_k_max 11 _diffrn_reflns_limit_l_min -20 _diffrn_reflns_limit_l_max 19 _diffrn_reflns_theta_min 2.21 _diffrn_reflns_theta_max 25.50 _reflns_number_total 3455 _reflns_number_gt 1571 _reflns_threshold_expression >2sigma(I) _computing_data_collection ? _computing_cell_refinement ? _computing_data_reduction ? _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics ? _computing_publication_material ? _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0854P)^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 SHELXL _refine_ls_extinction_coef 0.0020(4) _refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^ _refine_ls_number_reflns 3455 _refine_ls_number_parameters 256 _refine_ls_number_restraints 34 _refine_ls_R_factor_all 0.1492 _refine_ls_R_factor_gt 0.0624 _refine_ls_wR_factor_ref 0.1924 _refine_ls_wR_factor_gt 0.1474 _refine_ls_goodness_of_fit_ref 0.989 _refine_ls_restrained_S_all 1.002 _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 S1 S 0.17743(5) 0.67484(12) 0.14496(8) 0.0791(5) Uani 1 1 d . . . C6 C 0.17545(15) 0.1670(4) -0.0620(2) 0.0461(9) Uani 1 1 d . . . C8 C 0.16678(14) 0.2982(4) -0.0366(2) 0.0475(10) Uani 1 1 d . . . C5 C 0.19958(17) 0.0640(4) 0.0046(3) 0.0555(10) Uani 1 1 d . . . C7 C 0.15735(15) 0.1390(4) -0.1561(3) 0.0536(10) Uani 1 1 d . . . H7 H 0.1420 0.2072 -0.2007 0.064 Uiso 1 1 calc R . . C11 C 0.18718(17) 0.5140(4) 0.1380(3) 0.0583(11) Uani 1 1 d . . . C2 C 0.16111(17) 0.0156(4) -0.1863(3) 0.0552(10) Uani 1 1 d . . . C4 C 0.20399(19) -0.0594(4) -0.0241(3) 0.0711(12) Uani 1 1 d . . . H4 H 0.2204 -0.1275 0.0206 0.085 Uiso 1 1 calc R . . C9 C 0.13755(17) 0.4114(4) -0.1051(3) 0.0557(11) Uani 1 1 d . . . H9A H 0.0972 0.3878 -0.1611 0.067 Uiso 1 1 calc R . . H9B H 0.1632 0.4409 -0.1263 0.067 Uiso 1 1 calc R . . C10 C 0.13243(17) 0.5178(4) -0.0449(3) 0.0562(11) Uani 1 1 d . . . H10 H 0.1550 0.5961 -0.0423 0.067 Uiso 1 1 calc R . . C3 C 0.18445(19) -0.0838(4) -0.1179(3) 0.0699(12) Uani 1 1 d . . . H3 H 0.1869 -0.1687 -0.1358 0.084 Uiso 1 1 calc R . . C12 C 0.06701(18) 0.5563(4) -0.0818(3) 0.0592(11) Uani 1 1 d . . . C17 C 0.0241(2) 0.4660(5) -0.0928(3) 0.0678(12) Uani 1 1 d . . . C1 C 0.13904(19) -0.0104(4) -0.2892(3) 0.0754(13) Uani 1 1 d . . . H1A H 0.0972 -0.0412 -0.3246 0.113 Uiso 1 1 calc R . . H1B H 0.1648 -0.0759 -0.2908 0.113 Uiso 1 1 calc R . . H1C H 0.1410 0.0691 -0.3180 0.113 Uiso 1 1 calc R . . C16 C -0.0368(2) 0.5017(5) -0.1305(3) 0.0807(14) Uani 1 1 d . . . H16 H -0.0647 0.4405 -0.1355 0.097 Uiso 1 1 calc R . . C13 C 0.0476(2) 0.6838(5) -0.1118(3) 0.0831(14) Uani 1 1 d . . . H13 H 0.0754 0.7459 -0.1063 0.100 Uiso 1 1 calc R . . C18 C 0.0030(2) 0.2384(5) -0.0882(4) 0.1052(19) Uani 1 1 d D . . H18A H -0.0282 0.2355 -0.1563 0.126 Uiso 1 1 d R . . H18B H -0.0160 0.2480 -0.0537 0.126 Uiso 1 1 d R . . C14 C -0.0134(3) 0.7200(6) -0.1507(4) 0.1089(19) Uani 1 1 d . . . H14 H -0.0262 0.8062 -0.1701 0.131 Uiso 1 1 calc R . . C15 C -0.0544(2) 0.6276(7) -0.1598(4) 0.0993(18) Uani 1 1 d . . . H15 H -0.0951 0.6516 -0.1867 0.119 Uiso 1 1 calc R . . N1 N 0.21491(14) 0.4357(3) 0.2152(2) 0.0697(10) Uani 1 1 d . . . H1D H 0.2189 0.3533 0.2087 0.084 Uiso 1 1 calc R . . H1E H 0.2288 0.4676 0.2714 0.084 Uiso 1 1 calc R . . N2 N 0.18267(12) 0.3250(3) 0.0502(2) 0.0519(8) Uani 1 1 d . . . N3 N 0.16673(13) 0.4546(3) 0.0524(2) 0.0542(9) Uani 1 1 d . . . O2 O 0.22027(15) 0.0810(3) 0.09865(19) 0.0776(9) Uani 1 1 d . . . H2 H 0.2164 0.1582 0.1080 0.116 Uiso 1 1 calc R . . O3 O 0.04594(13) 0.3425(3) -0.0641(2) 0.0858(10) Uani 1 1 d . . . C20A C 0.0431(8) 0.1143(13) -0.0624(15) 0.131(5) Uani 0.50 1 d PDU . . H20A H 0.0732 0.0837 0.0018 0.157 Uiso 0.50 1 d PR . . C20B C 0.0332(9) 0.1107(14) -0.0406(15) 0.156(6) Uani 0.50 1 d PDU . . H20B H 0.0483 0.1103 0.0266 0.188 Uiso 0.50 1 d PR . . C21B C 0.0267(7) 0.0604(17) -0.1451(12) 0.164(5) Uani 0.50 1 d PDU . . H21A H -0.0038 0.0948 -0.2078 0.197 Uiso 0.50 1 d PR . . H21B H 0.0485 -0.0186 -0.1392 0.197 Uiso 0.50 1 d PR . . C21A C 0.0519(7) 0.0058(15) -0.0597(13) 0.162(5) Uani 0.50 1 d PDU . . H20C H 0.0373 0.0034 -0.1265 0.194 Uiso 0.50 1 d PR . . H21C H 0.0751 -0.0666 -0.0181 0.194 Uiso 0.50 1 d PR . . 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 S1 0.0802(9) 0.0682(9) 0.0764(9) -0.0234(6) 0.0367(7) -0.0054(6) C6 0.042(2) 0.050(2) 0.039(2) 0.0020(18) 0.0185(17) 0.0036(17) C8 0.041(2) 0.054(3) 0.040(2) -0.0017(18) 0.0182(17) -0.0006(17) C5 0.058(3) 0.061(3) 0.045(2) 0.002(2) 0.028(2) 0.003(2) C7 0.045(2) 0.058(3) 0.047(2) 0.0024(19) 0.0198(19) -0.0031(18) C11 0.046(2) 0.069(3) 0.050(3) -0.013(2) 0.020(2) -0.009(2) C2 0.049(2) 0.061(3) 0.056(2) -0.013(2) 0.030(2) -0.008(2) C4 0.081(3) 0.060(3) 0.071(3) 0.009(2) 0.042(3) 0.009(2) C9 0.054(2) 0.057(3) 0.047(2) 0.0030(19) 0.0226(19) 0.0022(19) C10 0.053(2) 0.058(3) 0.049(2) -0.002(2) 0.023(2) -0.0048(19) C3 0.074(3) 0.057(3) 0.081(3) -0.012(3) 0.046(3) -0.003(2) C12 0.052(3) 0.062(3) 0.052(2) -0.006(2) 0.022(2) 0.000(2) C17 0.064(3) 0.063(3) 0.064(3) -0.009(2) 0.029(2) 0.003(3) C1 0.072(3) 0.087(4) 0.068(3) -0.028(2) 0.040(2) -0.022(2) C16 0.062(3) 0.096(4) 0.080(3) -0.017(3) 0.037(3) -0.012(3) C13 0.068(3) 0.073(3) 0.095(4) 0.004(3) 0.039(3) 0.022(3) C18 0.075(4) 0.097(5) 0.121(4) 0.016(3) 0.042(3) -0.018(3) C14 0.086(4) 0.090(4) 0.125(5) 0.000(4) 0.045(4) 0.029(3) C15 0.062(4) 0.112(5) 0.098(4) -0.016(4) 0.029(3) 0.013(3) N1 0.070(2) 0.079(3) 0.042(2) -0.0186(19) 0.0209(18) -0.0059(19) N2 0.0474(18) 0.056(2) 0.0413(18) -0.0067(15) 0.0185(15) 0.0000(15) N3 0.053(2) 0.054(2) 0.046(2) -0.0050(16) 0.0218(16) -0.0010(16) O2 0.103(2) 0.073(2) 0.0491(17) 0.0113(15) 0.0378(16) 0.0149(18) O3 0.0628(19) 0.073(2) 0.108(2) 0.0002(19) 0.0395(17) -0.0149(17) C20A 0.091(6) 0.141(8) 0.177(9) 0.043(8) 0.085(6) -0.033(6) C20B 0.104(8) 0.157(9) 0.183(9) 0.027(9) 0.067(7) -0.016(7) C21B 0.112(7) 0.151(9) 0.201(10) 0.037(9) 0.071(8) -0.018(7) C21A 0.109(7) 0.148(9) 0.189(9) 0.017(9) 0.062(7) -0.014(7) _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 S1 C11 1.673(4) . ? C6 C5 1.397(5) . ? C6 C7 1.398(5) . ? C6 C8 1.460(5) . ? C8 N2 1.298(4) . ? C8 C9 1.499(5) . ? C5 O2 1.360(4) . ? C5 C4 1.375(5) . ? C7 C2 1.380(5) . ? C7 H7 0.9300 . ? C11 N1 1.334(5) . ? C11 N3 1.359(5) . ? C2 C3 1.388(5) . ? C2 C1 1.503(5) . ? C4 C3 1.376(6) . ? C4 H4 0.9300 . ? C9 C10 1.539(5) . ? C9 H9A 0.9700 . ? C9 H9B 0.9700 . ? C10 N3 1.493(4) . ? C10 C12 1.513(5) . ? C10 H10 0.9800 . ? C3 H3 0.9300 . ? C12 C13 1.382(6) . ? C12 C17 1.384(6) . ? C17 O3 1.353(5) . ? C17 C16 1.397(6) . ? C1 H1A 0.9600 . ? C1 H1B 0.9600 . ? C1 H1C 0.9600 . ? C16 C15 1.358(7) . ? C16 H16 0.9300 . ? C13 C14 1.399(6) . ? C13 H13 0.9300 . ? C18 O3 1.431(5) . ? C18 C20B 1.498(9) . ? C18 C20A 1.543(9) . ? C18 H18A 0.9601 . ? C18 H18B 0.9599 . ? C14 C15 1.372(7) . ? C14 H14 0.9300 . ? C15 H15 0.9300 . ? N1 H1D 0.8600 . ? N1 H1E 0.8600 . ? N2 N3 1.392(4) . ? O2 H2 0.8200 . ? C20A C20B 0.56(3) . ? C20A C21A 1.125(19) . ? C20A C21B 1.318(10) . ? C20A H20A 0.9600 . ? C20B C21A 1.290(10) . ? C20B H20B 0.9600 . ? C21B C21A 1.32(2) . ? C21B H21A 0.9600 . ? C21B H21B 0.9601 . ? C21A H20C 0.9600 . ? C21A H21C 0.9599 . ? 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 C6 C7 117.5(4) . . ? C5 C6 C8 122.0(3) . . ? C7 C6 C8 120.5(3) . . ? N2 C8 C6 121.1(3) . . ? N2 C8 C9 113.6(3) . . ? C6 C8 C9 125.3(3) . . ? O2 C5 C4 117.7(4) . . ? O2 C5 C6 122.5(4) . . ? C4 C5 C6 119.8(4) . . ? C2 C7 C6 123.5(4) . . ? C2 C7 H7 118.3 . . ? C6 C7 H7 118.3 . . ? N1 C11 N3 115.7(4) . . ? N1 C11 S1 122.7(3) . . ? N3 C11 S1 121.7(3) . . ? C7 C2 C3 116.8(4) . . ? C7 C2 C1 121.5(4) . . ? C3 C2 C1 121.7(4) . . ? C5 C4 C3 121.0(4) . . ? C5 C4 H4 119.5 . . ? C3 C4 H4 119.5 . . ? C8 C9 C10 103.6(3) . . ? C8 C9 H9A 111.0 . . ? C10 C9 H9A 111.0 . . ? C8 C9 H9B 111.0 . . ? C10 C9 H9B 111.0 . . ? H9A C9 H9B 109.0 . . ? N3 C10 C12 113.8(3) . . ? N3 C10 C9 101.1(3) . . ? C12 C10 C9 114.5(3) . . ? N3 C10 H10 109.0 . . ? C12 C10 H10 109.0 . . ? C9 C10 H10 109.0 . . ? C4 C3 C2 121.4(4) . . ? C4 C3 H3 119.3 . . ? C2 C3 H3 119.3 . . ? C13 C12 C17 118.2(4) . . ? C13 C12 C10 119.5(4) . . ? C17 C12 C10 122.2(4) . . ? O3 C17 C12 114.9(4) . . ? O3 C17 C16 123.4(4) . . ? C12 C17 C16 121.7(4) . . ? C2 C1 H1A 109.5 . . ? C2 C1 H1B 109.5 . . ? H1A C1 H1B 109.5 . . ? C2 C1 H1C 109.5 . . ? H1A C1 H1C 109.5 . . ? H1B C1 H1C 109.5 . . ? C15 C16 C17 118.6(5) . . ? C15 C16 H16 120.7 . . ? C17 C16 H16 120.7 . . ? C12 C13 C14 120.5(5) . . ? C12 C13 H13 119.8 . . ? C14 C13 H13 119.8 . . ? O3 C18 C20B 113.5(9) . . ? O3 C18 C20A 102.9(8) . . ? C20B C18 C20A 21.1(12) . . ? O3 C18 H18A 111.5 . . ? C20B C18 H18A 116.6 . . ? C20A C18 H18A 107.4 . . ? O3 C18 H18B 110.5 . . ? C20B C18 H18B 93.7 . . ? C20A C18 H18B 114.8 . . ? H18A C18 H18B 109.6 . . ? C15 C14 C13 119.5(5) . . ? C15 C14 H14 120.3 . . ? C13 C14 H14 120.3 . . ? C16 C15 C14 121.5(5) . . ? C16 C15 H15 119.2 . . ? C14 C15 H15 119.2 . . ? C11 N1 H1D 120.0 . . ? C11 N1 H1E 120.0 . . ? H1D N1 H1E 120.0 . . ? C8 N2 N3 108.5(3) . . ? C11 N3 N2 120.3(3) . . ? C11 N3 C10 126.7(3) . . ? N2 N3 C10 112.7(3) . . ? C5 O2 H2 109.5 . . ? C17 O3 C18 118.8(4) . . ? C20B C20A C21A 94(2) . . ? C20B C20A C21B 132(5) . . ? C21A C20A C21B 64.6(13) . . ? C20B C20A C18 74.9(14) . . ? C21A C20A C18 155.3(18) . . ? C21B C20A C18 106.3(15) . . ? C20B C20A H20A 68.7 . . ? C21A C20A H20A 67.3 . . ? C21B C20A H20A 128.1 . . ? C18 C20A H20A 125.5 . . ? C20B C20A H20B 27.4 . . ? C21A C20A H20B 91.9 . . ? C21B C20A H20B 151.0 . . ? C18 C20A H20B 87.9 . . ? H20A C20A H20B 44.2 . . ? C20B C20A H20C 121.5 . . ? C21A C20A H20C 39.5 . . ? C21B C20A H20C 25.2 . . ? C18 C20A H20C 129.5 . . ? H20A C20A H20C 104.2 . . ? H20B C20A H20C 129.8 . . ? C20A C20B C21A 60(2) . . ? C20A C20B C18 84.0(17) . . ? C21A C20B C18 138.4(19) . . ? C20A C20B C21B 34(3) . . ? C21A C20B C21B 48.7(12) . . ? C18 C20B C21B 89.8(11) . . ? C20A C20B H20A 76.8 . . ? C21A C20B H20A 60.9 . . ? C18 C20B H20A 134.6 . . ? C21B C20B H20A 96.2 . . ? C20A C20B H20B 137.1 . . ? C21A C20B H20B 109.0 . . ? C18 C20B H20B 111.9 . . ? C21B C20B H20B 157.1 . . ? H20A C20B H20B 63.7 . . ? C21A C21B C20A 50.6(10) . . ? C21A C21B C20B 47.5(10) . . ? C20A C21B C20B 13.8(14) . . ? C21A C21B H21A 160.7 . . ? C20A C21B H21A 125.2 . . ? C20B C21B H21A 122.9 . . ? C21A C21B H21B 68.3 . . ? C20A C21B H21B 114.9 . . ? C20B C21B H21B 115.5 . . ? H21A C21B H21B 120.0 . . ? C21A C21B H20C 43.7 . . ? C20A C21B H20C 94.1 . . ? C20B C21B H20C 90.5 . . ? H21A C21B H20C 136.5 . . ? H21B C21B H20C 28.8 . . ? C20A C21A C20B 25.6(15) . . ? C20A C21A C21B 64.8(10) . . ? C20B C21A C21B 83.9(18) . . ? C20A C21A H20A 49.5 . . ? C20B C21A H20A 43.6 . . ? C21B C21A H20A 111.8 . . ? C20A C21A H21B 104.5 . . ? C20B C21A H21B 126.4 . . ? C21B C21A H21B 42.9 . . ? H20A C21A H21B 138.8 . . ? C20A C21A H20C 92.3 . . ? C20B C21A H20C 110.8 . . ? C21B C21A H20C 27.5 . . ? H20A C21A H20C 136.7 . . ? H21B C21A H20C 18.5 . . ? C20A C21A H21C 144.7 . . ? C20B C21A H21C 129.1 . . ? C21B C21A H21C 146.9 . . ? H20A C21A H21C 95.1 . . ? H21B C21A H21C 104.1 . . ? H20C C21A H21C 120.0 . . ? _diffrn_measured_fraction_theta_max 0.999 _diffrn_reflns_theta_full 25.50 _diffrn_measured_fraction_theta_full 0.999 _refine_diff_density_max 0.297 _refine_diff_density_min -0.262 _refine_diff_density_rms 0.062 data_p2 _database_code_depnum_ccdc_archive 'CCDC 891148' #TrackingRef 'p.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C H O' _chemical_formula_weight 29.02 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' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting ? _symmetry_space_group_name_H-M ? loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y-1/2, z-1/2' _cell_length_a 14.8086(16) _cell_length_b 8.8273(10) _cell_length_c 12.8851(14) _cell_angle_alpha 90.00 _cell_angle_beta 108.871(2) _cell_angle_gamma 90.00 _cell_volume 1593.8(3) _cell_formula_units_Z 47 _cell_measurement_temperature 273(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description ? _exptl_crystal_colour ? _exptl_crystal_size_max ? _exptl_crystal_size_mid ? _exptl_crystal_size_min ? _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.421 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 705 _exptl_absorpt_coefficient_mu 0.132 _exptl_absorpt_correction_type ? _exptl_absorpt_correction_T_min ? _exptl_absorpt_correction_T_max ? _exptl_absorpt_process_details ? _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 ? _diffrn_measurement_method ? _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 8968 _diffrn_reflns_av_R_equivalents 0.0244 _diffrn_reflns_av_sigmaI/netI 0.0303 _diffrn_reflns_limit_h_min -17 _diffrn_reflns_limit_h_max 19 _diffrn_reflns_limit_k_min -11 _diffrn_reflns_limit_k_max 9 _diffrn_reflns_limit_l_min -13 _diffrn_reflns_limit_l_max 16 _diffrn_reflns_theta_min 2.73 _diffrn_reflns_theta_max 27.43 _reflns_number_total 3515 _reflns_number_gt 2542 _reflns_threshold_expression >2sigma(I) _computing_data_collection ? _computing_cell_refinement ? _computing_data_reduction ? _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics ? _computing_publication_material ? _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0884P)^2^+0.2703P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment mixed _refine_ls_extinction_method SHELXL _refine_ls_extinction_coef 0.054(6) _refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^ _refine_ls_number_reflns 3515 _refine_ls_number_parameters 201 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0649 _refine_ls_R_factor_gt 0.0459 _refine_ls_wR_factor_ref 0.1530 _refine_ls_wR_factor_gt 0.1328 _refine_ls_goodness_of_fit_ref 0.959 _refine_ls_restrained_S_all 0.959 _refine_ls_shift/su_max 0.026 _refine_ls_shift/su_mean 0.005 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 C1 C 0.40345(10) 0.72982(16) 0.33872(11) 0.0443(3) Uani 1 1 d . . . O1 O 0.25915(9) 0.63950(17) 0.21542(9) 0.0699(4) Uani 1 1 d . . . C3 C 0.28976(10) 0.55712(17) 0.39645(12) 0.0484(4) Uani 1 1 d . . . H3 H 0.3343 0.5475 0.4661 0.058 Uiso 1 1 calc R . . C4 C 0.46825(10) 0.74039(17) 0.44591(12) 0.0477(4) Uani 1 1 d . . . H4 H 0.4548 0.6882 0.5019 0.057 Uiso 1 1 calc R . . O3 O 0.36667(10) 0.80923(17) 0.15043(9) 0.0734(4) Uani 1 1 d . . . H3A H 0.3185 0.7603 0.1460 0.110 Uiso 1 1 calc R . . C6 C 0.20439(10) 0.49438(17) 0.37500(12) 0.0474(4) Uani 1 1 d . . . H6 H 0.1629 0.5059 0.3038 0.057 Uiso 1 1 calc R . . C7 C 0.31474(10) 0.64164(17) 0.31146(11) 0.0476(4) Uani 1 1 d . . . C8 C 0.16777(10) 0.40941(17) 0.44993(12) 0.0480(4) Uani 1 1 d . . . O2 O 0.01749(8) 0.42319(16) 0.31572(10) 0.0696(4) Uani 1 1 d . . . C10 C 0.07023(11) 0.37185(19) 0.41688(13) 0.0541(4) Uani 1 1 d . . . C11 C 0.42494(12) 0.80992(18) 0.25502(13) 0.0546(4) Uani 1 1 d . . . C12 C 0.50824(14) 0.8938(2) 0.28031(16) 0.0687(5) Uani 1 1 d . . . H12 H 0.5228 0.9459 0.2250 0.082 Uiso 1 1 calc R . . C13 C 0.55093(11) 0.82498(18) 0.47153(14) 0.0539(4) Uani 1 1 d . . . C14 C 0.22556(12) 0.3608(2) 0.55305(14) 0.0602(4) Uani 1 1 d . . . H14 H 0.2900 0.3860 0.5769 0.072 Uiso 1 1 calc R . . C15 C 0.56926(13) 0.9009(2) 0.38549(17) 0.0673(5) Uani 1 1 d . . . H15 H 0.6247 0.9581 0.4002 0.081 Uiso 1 1 calc R . . C16 C 0.03392(13) 0.2877(2) 0.48532(17) 0.0712(5) Uani 1 1 d . . . H16 H -0.0306 0.2629 0.4632 0.085 Uiso 1 1 calc R . . C17 C 0.61785(12) 0.8377(2) 0.58716(15) 0.0685(5) Uani 1 1 d . . . H17A H 0.5937 0.7788 0.6350 0.103 Uiso 1 1 calc R . . H17B H 0.6229 0.9419 0.6097 0.103 Uiso 1 1 calc R . . H17C H 0.6797 0.8006 0.5906 0.103 Uiso 1 1 calc R . . C18 C 0.18917(15) 0.2763(2) 0.62025(16) 0.0758(5) Uani 1 1 d . . . H18 H 0.2289 0.2433 0.6882 0.091 Uiso 1 1 calc R . . C19 C -0.08214(12) 0.3877(3) 0.27356(18) 0.0751(5) Uani 1 1 d . . . H19A H -0.1146 0.4215 0.3238 0.090 Uiso 1 1 calc R . . H19B H -0.0915 0.2793 0.2628 0.090 Uiso 1 1 calc R . . C20 C 0.09349(16) 0.2410(3) 0.58595(17) 0.0795(6) Uani 1 1 d . . . H20 H 0.0688 0.1848 0.6316 0.095 Uiso 1 1 calc R . . C21 C -0.11965(14) 0.4697(3) 0.1662(2) 0.0875(7) Uani 1 1 d . . . H21 H -0.1134 0.5746 0.1680 0.105 Uiso 1 1 calc R . . C23 C -0.15907(18) 0.4094(4) 0.0732(2) 0.1047(8) Uani 1 1 d . . . H23A H -0.1668 0.3049 0.0674 0.126 Uiso 1 1 calc R . . H23B H -0.1802 0.4697 0.0108 0.126 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 C1 0.0486(8) 0.0449(7) 0.0453(7) -0.0027(6) 0.0232(6) 0.0019(6) O1 0.0665(7) 0.0976(10) 0.0428(6) -0.0003(6) 0.0140(5) -0.0161(7) C3 0.0485(8) 0.0541(8) 0.0434(8) -0.0045(6) 0.0157(6) -0.0054(6) C4 0.0482(8) 0.0493(8) 0.0506(8) -0.0015(6) 0.0229(6) 0.0004(6) O3 0.0869(9) 0.0879(10) 0.0499(7) 0.0125(6) 0.0283(6) -0.0031(7) C6 0.0478(8) 0.0480(8) 0.0476(8) -0.0045(6) 0.0171(6) -0.0011(6) C7 0.0497(8) 0.0531(8) 0.0427(8) -0.0048(6) 0.0186(6) 0.0013(6) C8 0.0488(8) 0.0466(8) 0.0521(8) -0.0062(6) 0.0210(7) -0.0025(6) O2 0.0456(6) 0.0913(10) 0.0685(8) 0.0080(6) 0.0139(5) -0.0112(6) C10 0.0510(8) 0.0566(9) 0.0576(9) -0.0027(7) 0.0213(7) -0.0027(7) C11 0.0658(10) 0.0530(9) 0.0538(9) 0.0035(7) 0.0313(8) 0.0042(7) C12 0.0779(12) 0.0652(11) 0.0766(12) 0.0087(9) 0.0439(10) -0.0082(9) C13 0.0461(8) 0.0515(9) 0.0679(10) -0.0077(7) 0.0238(7) 0.0002(6) C14 0.0563(9) 0.0665(10) 0.0583(10) 0.0021(8) 0.0193(7) -0.0037(8) C15 0.0587(10) 0.0612(11) 0.0907(14) -0.0013(9) 0.0361(10) -0.0116(8) C16 0.0605(10) 0.0777(12) 0.0838(13) 0.0039(10) 0.0349(9) -0.0122(9) C17 0.0507(9) 0.0714(11) 0.0795(12) -0.0133(9) 0.0157(8) -0.0051(8) C18 0.0776(13) 0.0861(14) 0.0652(11) 0.0165(10) 0.0252(9) -0.0024(10) C19 0.0441(9) 0.0870(13) 0.0913(14) -0.0003(11) 0.0180(9) -0.0063(9) C20 0.0857(13) 0.0858(14) 0.0780(13) 0.0181(10) 0.0419(11) -0.0070(11) C21 0.0542(10) 0.0853(15) 0.1064(17) 0.0026(13) 0.0029(11) 0.0047(10) C23 0.0792(15) 0.119(2) 0.1072(19) 0.0251(16) 0.0188(14) -0.0130(14) _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 C1 C4 1.4070(19) . ? C1 C11 1.409(2) . ? C1 C7 1.468(2) . ? O1 C7 1.2452(17) . ? C3 C6 1.325(2) . ? C3 C7 1.468(2) . ? C4 C13 1.380(2) . ? O3 C11 1.345(2) . ? C6 C8 1.459(2) . ? C8 C14 1.395(2) . ? C8 C10 1.407(2) . ? O2 C10 1.362(2) . ? O2 C19 1.432(2) . ? C10 C16 1.388(2) . ? C11 C12 1.384(2) . ? C12 C15 1.366(3) . ? C13 C15 1.395(2) . ? C13 C17 1.503(2) . ? C14 C18 1.378(3) . ? C16 C20 1.374(3) . ? C18 C20 1.376(3) . ? C19 C21 1.500(3) . ? C21 C23 1.268(3) . ? 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 C4 C1 C11 117.83(14) . . ? C4 C1 C7 122.90(13) . . ? C11 C1 C7 119.26(13) . . ? C6 C3 C7 120.70(14) . . ? C13 C4 C1 122.77(14) . . ? C3 C6 C8 127.65(14) . . ? O1 C7 C1 119.89(13) . . ? O1 C7 C3 119.25(13) . . ? C1 C7 C3 120.85(13) . . ? C14 C8 C10 117.99(14) . . ? C14 C8 C6 122.93(14) . . ? C10 C8 C6 119.07(14) . . ? C10 O2 C19 119.43(14) . . ? O2 C10 C16 124.49(15) . . ? O2 C10 C8 115.20(14) . . ? C16 C10 C8 120.31(15) . . ? O3 C11 C12 118.19(14) . . ? O3 C11 C1 122.29(15) . . ? C12 C11 C1 119.52(15) . . ? C15 C12 C11 120.77(16) . . ? C4 C13 C15 117.10(16) . . ? C4 C13 C17 121.81(15) . . ? C15 C13 C17 121.09(15) . . ? C18 C14 C8 121.39(16) . . ? C12 C15 C13 122.01(16) . . ? C20 C16 C10 119.84(17) . . ? C20 C18 C14 119.47(18) . . ? O2 C19 C21 105.83(16) . . ? C18 C20 C16 121.00(17) . . ? C23 C21 C19 126.1(2) . . ? _diffrn_measured_fraction_theta_max 0.964 _diffrn_reflns_theta_full 27.43 _diffrn_measured_fraction_theta_full 0.964 _refine_diff_density_max 0.226 _refine_diff_density_min -0.189 _refine_diff_density_rms 0.033