#------------------------------------------------------------------------------ #$Date: 2014-06-03 04:59:56 +0300 (Tue, 03 Jun 2014) $ #$Revision: 115377 $ #$URL: file:///home/coder/svn-repositories/cod/cif/1/51/64/1516471.cif $ #------------------------------------------------------------------------------ # # This file is available in the Crystallography Open Database (COD), # http://www.crystallography.net/ # # All data on this site have been placed in the public domain by the # contributors. # data_1516471 loop_ _publ_author_name 'Chen, Shenxi' 'Zhang, Yang' 'Niu, Shubin' 'Liu, Xingzhong' 'Che, Yongsheng' _publ_section_title ; Cytotoxic Cleistanthane and Cassane Diterpenoids from the Entomogenous FungusParaconiothyrium hawaiiense ; _journal_name_full 'Journal of Natural Products' _journal_page_first 140602072926000 _journal_paper_doi 10.1021/np500302e _journal_year 2014 _chemical_absolute_configuration ad _chemical_formula_moiety 'C20 H28 O4, H2 O' _chemical_formula_sum 'C20 H30 O5' _chemical_formula_weight 350.44 _chemical_name_systematic ; ? ; _space_group_crystal_system orthorhombic _space_group_IT_number 19 _space_group_name_Hall 'P 2ac 2ab' _space_group_name_H-M_alt 'P 21 21 21' _symmetry_space_group_name_Hall 'P 2ac 2ab' _symmetry_space_group_name_H-M 'P 21 21 21' _atom_sites_solution_hydrogens geom _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _audit_creation_date 2014-03-05 _audit_creation_method ; Olex2 1.1 (compiled 2011.02.15 svn.r1672, GUI svn.r3494) ; _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_formula_units_Z 4 _cell_length_a 7.2054(3) _cell_length_b 8.0628(3) _cell_length_c 31.8423(11) _cell_measurement_reflns_used 4182 _cell_measurement_temperature 97.20(10) _cell_measurement_theta_max 71.9150 _cell_measurement_theta_min 5.5580 _cell_volume 1849.90(12) _computing_cell_refinement ; CrysAlisPro, Agilent Technologies, Version 1.171.37.31 (release 14-01-2014 CrysAlis171 .NET) (compiled Jan 14 2014,18:38:05) ; _computing_data_collection ; CrysAlisPro, Agilent Technologies, Version 1.171.37.31 (release 14-01-2014 CrysAlis171 .NET) (compiled Jan 14 2014,18:38:05) ; _computing_data_reduction ; CrysAlisPro, Agilent Technologies, Version 1.171.37.31 (release 14-01-2014 CrysAlis171 .NET) (compiled Jan 14 2014,18:38:05) ; _computing_molecular_graphics ; O. V. Dolomanov, L. J. Bourhis, R. J. Gildea, J. A. K. Howard and H. Puschmann, OLEX2: a complete structure solution, refinement and analysis program. J. Appl. Cryst. (2009). 42, 339-341. ; _computing_publication_material ; O. V. Dolomanov, L. J. Bourhis, R. J. Gildea, J. A. K. Howard and H. Puschmann, OLEX2: a complete structure solution, refinement and analysis program. J. Appl. Cryst. (2009). 42, 339-341. ; _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_structure_solution 'A short history of SHELX (Sheldrick, 2007)' _diffrn_ambient_environment N~2~ _diffrn_ambient_temperature 97.20(10) _diffrn_detector 'CCD plate' _diffrn_detector_area_resol_mean 16.0971 _diffrn_detector_type Eos _diffrn_measured_fraction_theta_full 0.9990 _diffrn_measured_fraction_theta_max 0.9703 _diffrn_measurement_details ; 1 omega 33.00 70.00 1.0000 1.2000 omega____ theta____ kappa____ phi______ frames - 0.0000 37.0000 -60.0000 37 2 omega 12.00 120.00 1.0000 3.0000 omega____ theta____ kappa____ phi______ frames - 56.0000 19.0000 30.0000 108 3 omega 147.00 178.00 1.0000 6.0000 omega____ theta____ kappa____ phi______ frames - 112.0000 61.0000 -30.0000 31 4 omega 91.00 117.00 1.0000 6.0000 omega____ theta____ kappa____ phi______ frames - 112.0000 61.0000 -30.0000 26 5 omega 91.00 169.00 1.0000 6.0000 omega____ theta____ kappa____ phi______ frames - 112.0000 45.0000 -90.0000 78 6 omega 88.00 133.00 1.0000 6.0000 omega____ theta____ kappa____ phi______ frames - 112.0000 -61.0000 -180.0000 45 7 omega 67.00 178.00 1.0000 6.0000 omega____ theta____ kappa____ phi______ frames - 112.0000 15.0000 -150.0000 111 8 omega 54.00 125.00 1.0000 3.0000 omega____ theta____ kappa____ phi______ frames - 56.0000 57.0000 -180.0000 71 9 omega 40.00 85.00 1.0000 6.0000 omega____ theta____ kappa____ phi______ frames - 112.0000 -30.0000 -60.0000 45 10 omega 57.00 108.00 1.0000 6.0000 omega____ theta____ kappa____ phi______ frames - 112.0000 -94.0000 -120.0000 51 11 omega 46.00 72.00 1.0000 6.0000 omega____ theta____ kappa____ phi______ frames - 112.0000 -61.0000 -180.0000 26 12 omega 43.00 73.00 1.0000 6.0000 omega____ theta____ kappa____ phi______ frames - 112.0000 -30.0000 -180.0000 30 13 omega -3.00 57.00 1.0000 3.0000 omega____ theta____ kappa____ phi______ frames - 56.0000 -99.0000 -150.0000 60 14 omega -15.00 12.00 1.0000 1.2000 omega____ theta____ kappa____ phi______ frames - 0.0000 37.0000 -60.0000 27 15 omega -4.00 21.00 1.0000 1.2000 omega____ theta____ kappa____ phi______ frames - 0.0000 -99.0000 90.0000 25 16 omega -4.00 42.00 1.0000 1.2000 omega____ theta____ kappa____ phi______ frames - 0.0000 -99.0000 -180.0000 46 17 omega 30.00 94.00 1.0000 3.0000 omega____ theta____ kappa____ phi______ frames - 56.0000 37.0000 120.0000 64 18 omega -77.00 -32.00 1.0000 1.2000 omega____ theta____ kappa____ phi______ frames - 0.0000 178.0000 0.0000 45 19 omega -30.00 70.00 1.0000 1.2000 omega____ theta____ kappa____ phi______ frames - 0.0000 77.0000 -30.0000 100 20 omega -13.00 77.00 1.0000 3.0000 omega____ theta____ kappa____ phi______ frames - 56.0000 -57.0000 30.0000 90 21 omega -13.00 51.00 1.0000 3.0000 omega____ theta____ kappa____ phi______ frames - 56.0000 -57.0000 -90.0000 64 ; _diffrn_measurement_device 'four-circle diffractometer' _diffrn_measurement_device_type 'Xcalibur, Eos, Gemini' _diffrn_measurement_method '\w scans' _diffrn_orient_matrix_UB_11 0.1533073000 _diffrn_orient_matrix_UB_12 -0.0670534000 _diffrn_orient_matrix_UB_13 0.0291581000 _diffrn_orient_matrix_UB_21 0.1165422000 _diffrn_orient_matrix_UB_22 -0.0489540000 _diffrn_orient_matrix_UB_23 -0.0385966000 _diffrn_orient_matrix_UB_31 0.0931107000 _diffrn_orient_matrix_UB_32 0.1721963000 _diffrn_orient_matrix_UB_33 0.0004140000 _diffrn_radiation_monochromator graphite _diffrn_radiation_probe x-ray _diffrn_radiation_type 'Cu K\a' _diffrn_radiation_wavelength 1.54184 _diffrn_reflns_av_R_equivalents 0.0265 _diffrn_reflns_av_unetI/netI 0.0318 _diffrn_reflns_limit_h_max 8 _diffrn_reflns_limit_h_min -7 _diffrn_reflns_limit_k_max 9 _diffrn_reflns_limit_k_min -8 _diffrn_reflns_limit_l_max 38 _diffrn_reflns_limit_l_min -38 _diffrn_reflns_number 8427 _diffrn_reflns_theta_full 71.94 _diffrn_reflns_theta_max 71.94 _diffrn_reflns_theta_min 5.56 _diffrn_source 'Enhance (Cu) X-ray Source' _exptl_absorpt_coefficient_mu 0.722 _exptl_absorpt_correction_T_max 1.00000 _exptl_absorpt_correction_T_min 0.71729 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details ; CrysAlisPro, Agilent Technologies, Version 1.171.37.31 (release 14-01-2014 CrysAlis171 .NET) (compiled Jan 14 2014,18:38:05) Empirical absorption correction using spherical harmonics, implemented in SCALE3 ABSPACK scaling algorithm. ; _exptl_crystal_density_diffrn 1.258 _exptl_crystal_density_method 'not measured' _exptl_crystal_description ; ; _exptl_crystal_F_000 760 _exptl_crystal_size_max 0.40 _exptl_crystal_size_mid 0.15 _exptl_crystal_size_min 0.03 _refine_diff_density_max 0.289 _refine_diff_density_min -0.268 _refine_diff_density_rms 0.045 _refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881' _refine_ls_abs_structure_Flack 0.27(16) _refine_ls_extinction_method none _refine_ls_goodness_of_fit_ref 1.023 _refine_ls_hydrogen_treatment mixed _refine_ls_matrix_type full _refine_ls_number_parameters 230 _refine_ls_number_reflns 3528 _refine_ls_number_restraints 0 _refine_ls_restrained_S_all 1.023 _refine_ls_R_factor_all 0.0389 _refine_ls_R_factor_gt 0.0369 _refine_ls_shift/su_max 0.038 _refine_ls_shift/su_mean 0.003 _refine_ls_structure_factor_coef Fsqd _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0611P)^2^+0.2789P] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_gt 0.0945 _refine_ls_wR_factor_ref 0.0967 _reflns_number_gt 3365 _reflns_number_total 3528 _reflns_threshold_expression >2sigma(I) _[local]_cod_data_source_file np500302e_si_003.cif _[local]_cod_data_source_block exp_1959 _cod_database_code 1516471 _reflns_odcompleteness_completeness 99.90 _reflns_odcompleteness_iscentric 1 _reflns_odcompleteness_theta 66.97 loop_ _space_group_symop_id _space_group_symop_operation_xyz 1 'x, y, z' 2 '-x+1/2, -y, z+1/2' 3 'x+1/2, -y+1/2, -z' 4 '-x, y+1/2, -z+1/2' 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 H3 H -0.3933 0.2535 0.2253 0.028 Uiso 1 1 calc R H3A H -0.3180 0.2983 0.1608 0.020 Uiso 1 1 calc R H4 H 0.2618 0.3495 0.2031 0.025 Uiso 1 1 calc R H4A H -0.1855 0.0334 0.1530 0.021 Uiso 1 1 calc R H4B H -0.0169 0.0853 0.1810 0.021 Uiso 1 1 calc R H5A H 0.1193 0.1222 0.1194 0.019 Uiso 1 1 calc R H5B H -0.0690 0.1516 0.0960 0.019 Uiso 1 1 calc R H8 H 0.1891 0.6237 0.1972 0.017 Uiso 1 1 calc R H9A H 0.3818 0.6689 0.1461 0.020 Uiso 1 1 calc R H9B H 0.2283 0.7979 0.1346 0.020 Uiso 1 1 calc R H10 H 0.1330 0.6539 0.0782 0.018 Uiso 1 1 calc R H11 H 0.3261 0.3700 0.1083 0.018 Uiso 1 1 calc R H12A H 0.2085 0.2240 0.0503 0.023 Uiso 1 1 calc R H12B H 0.1126 0.3858 0.0335 0.023 Uiso 1 1 calc R H13A H 0.5031 0.3414 0.0399 0.027 Uiso 1 1 calc R H13B H 0.3934 0.3475 -0.0027 0.027 Uiso 1 1 calc R H15 H 0.5260 0.6230 0.0826 0.021 Uiso 1 1 calc R H16A H 0.4442 0.5984 -0.0369 0.035 Uiso 1 1 calc R H16B H 0.4590 0.7710 -0.0117 0.035 Uiso 1 1 calc R H17 H 0.3313 0.9000 0.0495 0.026 Uiso 1 1 calc R H18A H 0.6527 0.8910 0.0958 0.039 Uiso 1 1 calc R H18B H 0.5514 1.0544 0.0778 0.039 Uiso 1 1 calc R H19A H 0.0080 0.2996 0.2469 0.025 Uiso 1 1 calc R H19B H -0.1574 0.4202 0.2565 0.025 Uiso 1 1 calc R H19C H 0.0398 0.4920 0.2464 0.025 Uiso 1 1 calc R H20A H -0.2388 0.4220 0.1138 0.023 Uiso 1 1 calc R H20B H -0.1364 0.4283 0.0704 0.023 Uiso 1 1 calc R H20C H -0.1154 0.5754 0.1022 0.023 Uiso 1 1 calc R C1 C -0.1823(2) 0.5778(2) 0.18500(5) 0.0150(3) Uani 1 1 d . C2 C -0.0959(2) 0.4091(2) 0.19300(5) 0.0147(3) Uani 1 1 d . C3 C -0.2237(2) 0.2605(2) 0.18083(5) 0.0163(3) Uani 1 1 d . C4 C -0.1055(2) 0.1255(2) 0.16048(5) 0.0173(3) Uani 1 1 d . C5 C 0.0024(2) 0.1817(2) 0.12066(5) 0.0156(3) Uani 1 1 d . C6 C 0.0426(2) 0.3709(2) 0.11937(5) 0.0135(3) Uani 1 1 d . C7 C 0.0824(2) 0.4223(2) 0.16572(5) 0.0140(3) Uani 1 1 d . C8 C 0.1291(2) 0.6071(2) 0.16988(5) 0.0139(3) Uani 1 1 d . C9 C 0.2546(2) 0.6802(2) 0.13653(5) 0.0165(3) Uani 1 1 d . C10 C 0.2423(2) 0.6066(2) 0.09200(5) 0.0149(3) Uani 1 1 d . C11 C 0.2185(2) 0.4159(2) 0.09344(5) 0.0149(3) Uani 1 1 d . C12 C 0.2189(2) 0.3438(2) 0.04887(5) 0.0190(3) Uani 1 1 d . C13 C 0.3977(2) 0.3910(2) 0.02571(5) 0.0221(4) Uani 1 1 d . C14 C 0.4224(2) 0.5761(2) 0.02414(5) 0.0207(4) Uani 1 1 d . C15 C 0.4168(2) 0.6602(2) 0.06680(5) 0.0175(3) Uani 1 1 d . C16 C 0.4440(3) 0.6564(3) -0.01170(6) 0.0292(4) Uani 1 1 d . C17 C 0.4256(3) 0.8465(2) 0.06416(5) 0.0218(4) Uani 1 1 d . C18 C 0.5560(3) 0.9398(3) 0.08088(7) 0.0329(5) Uani 1 1 d . C19 C -0.0468(2) 0.4048(2) 0.24014(5) 0.0170(3) Uani 1 1 d . C20 C -0.1282(2) 0.4574(2) 0.09955(5) 0.0153(3) Uani 1 1 d . O1 O -0.34247(16) 0.61761(15) 0.19019(4) 0.0192(3) Uani 1 1 d . O2 O -0.05480(16) 0.68761(14) 0.17150(3) 0.0165(2) Uani 1 1 d . O3 O -0.31318(17) 0.18974(14) 0.21674(4) 0.0186(3) Uani 1 1 d . O4 O 0.23211(15) 0.32281(15) 0.17922(3) 0.0164(2) Uani 1 1 d . H5C H 0.3910 0.3041 0.2791 0.027 Uiso 1 1 d R H5D H 0.3888 0.4857 0.2671 0.027 Uiso 1 1 d R O5 O 0.42118(16) 0.37828(14) 0.25664(3) 0.0181(2) Uani 1 1 d . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 C1 0.0184(8) 0.0138(7) 0.0127(7) -0.0030(6) -0.0015(6) 0.0019(7) C2 0.0158(7) 0.0136(8) 0.0147(7) -0.0015(6) 0.0004(6) 0.0024(7) C3 0.0185(8) 0.0136(7) 0.0167(7) 0.0004(6) -0.0016(6) -0.0004(7) C4 0.0215(8) 0.0109(7) 0.0196(7) -0.0013(6) -0.0004(6) -0.0006(7) C5 0.0178(7) 0.0124(8) 0.0168(7) -0.0021(6) 0.0013(6) 0.0010(6) C6 0.0140(7) 0.0122(7) 0.0144(7) 0.0000(6) -0.0008(6) 0.0014(6) C7 0.0142(7) 0.0140(7) 0.0136(7) 0.0007(6) -0.0015(6) 0.0018(6) C8 0.0139(7) 0.0138(8) 0.0139(7) -0.0017(6) -0.0015(6) 0.0018(6) C9 0.0165(8) 0.0140(7) 0.0190(8) 0.0000(6) -0.0023(6) -0.0013(7) C10 0.0133(7) 0.0149(8) 0.0165(7) 0.0010(6) -0.0007(6) -0.0005(6) C11 0.0151(7) 0.0142(7) 0.0154(7) -0.0001(6) -0.0007(6) 0.0008(6) C12 0.0220(8) 0.0183(8) 0.0168(7) -0.0021(6) 0.0019(6) -0.0008(7) C13 0.0225(8) 0.0260(9) 0.0179(7) -0.0027(7) 0.0036(7) 0.0016(8) C14 0.0119(7) 0.0277(9) 0.0226(8) -0.0018(7) 0.0028(6) -0.0014(7) C15 0.0141(7) 0.0194(8) 0.0189(7) 0.0017(6) -0.0018(6) -0.0008(7) C16 0.0313(10) 0.0331(11) 0.0233(9) -0.0013(8) 0.0064(7) -0.0078(9) C17 0.0210(8) 0.0227(9) 0.0217(8) 0.0034(7) 0.0051(6) -0.0010(8) C18 0.0334(11) 0.0253(10) 0.0400(11) -0.0010(8) 0.0030(9) -0.0093(9) C19 0.0187(8) 0.0169(8) 0.0153(7) 0.0003(6) 0.0007(6) 0.0007(7) C20 0.0156(8) 0.0164(8) 0.0140(7) -0.0004(6) -0.0014(6) -0.0013(6) O1 0.0167(6) 0.0167(6) 0.0241(6) -0.0032(5) -0.0001(5) 0.0031(5) O2 0.0176(6) 0.0110(5) 0.0208(5) 0.0008(4) -0.0007(4) 0.0021(5) O3 0.0191(6) 0.0149(5) 0.0216(6) 0.0018(5) 0.0054(5) 0.0013(5) O4 0.0170(5) 0.0170(5) 0.0151(5) -0.0002(5) -0.0042(4) 0.0054(5) O5 0.0208(5) 0.0142(5) 0.0195(5) 0.0013(4) 0.0041(5) -0.0002(5) loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle O1 C1 C2 127.31(15) O1 C1 O2 121.37(15) O2 C1 C2 111.30(13) C1 C2 C3 113.88(13) C1 C2 C7 100.59(13) C1 C2 C19 106.12(13) C7 C2 C3 113.69(13) C19 C2 C3 111.08(13) C19 C2 C7 110.81(13) C2 C3 H3A 109.4 C4 C3 H3A 109.4 C4 C3 C2 108.87(13) O3 C3 H3A 109.4 O3 C3 C2 111.95(13) O3 C3 C4 107.83(13) H4A C4 H4B 107.6 C3 C4 H4A 108.6 C3 C4 H4B 108.6 C3 C4 C5 114.67(13) C5 C4 H4A 108.6 C5 C4 H4B 108.6 H5A C5 H5B 107.7 C4 C5 H5A 108.8 C4 C5 H5B 108.8 C6 C5 H5A 108.8 C6 C5 H5B 108.8 C6 C5 C4 113.64(13) C5 C6 C7 105.67(12) C5 C6 C11 113.25(13) C11 C6 C7 106.91(12) C20 C6 C5 107.71(13) C20 C6 C7 114.35(13) C20 C6 C11 109.05(12) C2 C7 C6 111.01(12) C8 C7 C2 101.52(12) C8 C7 C6 112.34(12) O4 C7 C2 115.00(12) O4 C7 C6 106.12(12) O4 C7 C8 111.01(13) C7 C8 H8 107.8 C9 C8 H8 107.8 C9 C8 C7 116.65(13) O2 C8 H8 107.8 O2 C8 C7 103.49(12) O2 C8 C9 112.95(13) H9A C9 H9B 107.2 C8 C9 H9A 107.9 C8 C9 H9B 107.9 C8 C9 C10 117.51(13) C10 C9 H9A 107.9 C10 C9 H9B 107.9 C9 C10 H10 108.1 C9 C10 C11 111.20(12) C9 C10 C15 108.81(13) C11 C10 H10 108.1 C11 C10 C15 112.41(13) C15 C10 H10 108.1 C6 C11 H11 107.5 C10 C11 H11 107.5 C10 C11 C6 109.72(13) C12 C11 H11 107.5 C12 C11 C6 113.87(13) C12 C11 C10 110.41(13) H12A C12 H12B 108.1 C11 C12 H12A 109.5 C11 C12 H12B 109.5 C13 C12 H12A 109.5 C13 C12 H12B 109.5 C13 C12 C11 110.66(13) H13A C13 H13B 108.0 C12 C13 H13A 109.4 C12 C13 H13B 109.4 C14 C13 H13A 109.4 C14 C13 H13B 109.4 C14 C13 C12 111.22(15) C13 C14 C15 114.20(15) C16 C14 C13 121.94(17) C16 C14 C15 123.85(17) C10 C15 H15 107.5 C14 C15 H15 107.5 C14 C15 C10 111.07(13) C17 C15 H15 107.5 C17 C15 C10 109.88(14) C17 C15 C14 113.22(14) H16A C16 H16B 120.0 C14 C16 H16A 120.0 C14 C16 H16B 120.0 C15 C17 H17 117.4 C18 C17 H17 117.4 C18 C17 C15 125.27(18) H18A C18 H18B 120.0 C17 C18 H18A 120.0 C17 C18 H18B 120.0 H19A C19 H19B 109.5 H19A C19 H19C 109.5 H19B C19 H19C 109.5 C2 C19 H19A 109.5 C2 C19 H19B 109.5 C2 C19 H19C 109.5 H20A C20 H20B 109.5 H20A C20 H20C 109.5 H20B C20 H20C 109.5 C6 C20 H20A 109.5 C6 C20 H20B 109.5 C6 C20 H20C 109.5 C1 O2 C8 109.55(12) C3 O3 H3 109.5 C7 O4 H4 109.5 H5C O5 H5D 104.5 loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance C2 C1 1.517(2) C3 H3A 0.9800 C3 C2 1.560(2) C4 H4A 0.9700 C4 H4B 0.9700 C4 C3 1.527(2) C4 C5 1.555(2) C5 H5A 0.9700 C5 H5B 0.9700 C6 C5 1.554(2) C6 C11 1.555(2) C6 C20 1.549(2) C7 C2 1.555(2) C7 C6 1.559(2) C7 C8 1.533(2) C8 H8 0.9800 C8 C9 1.514(2) C9 H9A 0.9700 C9 H9B 0.9700 C9 C10 1.539(2) C10 H10 0.9800 C10 C15 1.553(2) C11 H11 0.9800 C11 C10 1.548(2) C12 H12A 0.9700 C12 H12B 0.9700 C12 C11 1.533(2) C13 H13A 0.9700 C13 H13B 0.9700 C13 C12 1.532(2) C13 C14 1.504(3) C14 C15 1.519(2) C14 C16 1.321(3) C15 H15 0.9800 C16 H16A 0.9300 C16 H16B 0.9300 C17 H17 0.9300 C17 C15 1.506(2) C17 C18 1.316(3) C18 H18A 0.9300 C18 H18B 0.9300 C19 H19A 0.9600 C19 H19B 0.9600 C19 H19C 0.9600 C19 C2 1.543(2) C20 H20A 0.9600 C20 H20B 0.9600 C20 H20C 0.9600 O1 C1 1.209(2) O2 C1 1.346(2) O2 C8 1.4763(19) O3 H3 0.8200 O3 C3 1.4312(19) O4 H4 0.8200 O4 C7 1.4113(19) O5 H5C 0.9570 O5 H5D 0.9570 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 C1 O2 C8 C7 23.66(15) C1 O2 C8 C9 150.71(13) C2 C7 C6 C5 -68.25(16) C2 C7 C6 C11 170.83(13) C2 C7 C6 C20 50.03(17) C2 C7 C8 C9 -159.94(13) C2 C7 C8 O2 -35.26(14) C3 C2 C1 O1 38.2(2) C3 C2 C1 O2 -143.14(13) C3 C4 C5 C6 25.36(19) C4 C3 C2 C1 140.31(13) C4 C3 C2 C7 25.87(18) C4 C3 C2 C19 -99.94(15) C5 C4 C3 C2 -58.32(17) C5 C4 C3 O3 -179.98(13) C5 C6 C11 C10 177.20(12) C5 C6 C11 C12 52.89(18) C6 C7 C2 C1 -86.12(15) C6 C7 C2 C3 36.00(18) C6 C7 C2 C19 161.96(13) C6 C7 C8 C9 -41.30(18) C6 C7 C8 O2 83.38(14) C6 C11 C10 C9 57.27(16) C6 C11 C10 C15 179.54(12) C7 C2 C1 O1 160.24(16) C7 C2 C1 O2 -21.14(15) C7 C6 C5 C4 36.30(17) C7 C6 C11 C10 -66.83(15) C7 C6 C11 C12 168.86(13) C7 C8 C9 C10 31.8(2) C8 C7 C2 C1 33.46(14) C8 C7 C2 C3 155.59(13) C8 C7 C2 C19 -78.45(15) C8 C7 C6 C5 178.85(12) C8 C7 C6 C11 57.93(16) C8 C7 C6 C20 -62.87(17) C8 C9 C10 C11 -39.25(19) C8 C9 C10 C15 -163.58(14) C8 O2 C1 C2 -1.24(16) C8 O2 C1 O1 177.47(14) C9 C10 C15 C14 173.92(14) C9 C10 C15 C17 -60.02(17) C11 C6 C5 C4 153.00(13) C11 C10 C15 C14 50.30(18) C11 C10 C15 C17 176.36(13) C12 C11 C10 C9 -176.43(13) C12 C11 C10 C15 -54.16(17) C12 C13 C14 C15 54.80(19) C12 C13 C14 C16 -124.21(19) C13 C12 C11 C6 -179.01(14) C13 C12 C11 C10 57.05(18) C13 C14 C15 C10 -50.94(19) C13 C14 C15 C17 -175.13(15) C14 C13 C12 C11 -57.21(18) C16 C14 C15 C10 128.05(19) C16 C14 C15 C17 3.9(3) C18 C17 C15 C10 115.6(2) C18 C17 C15 C14 -119.6(2) C19 C2 C1 O1 -84.27(19) C19 C2 C1 O2 94.35(15) C20 C6 C5 C4 -86.33(16) C20 C6 C11 C10 57.29(16) C20 C6 C11 C12 -67.02(17) O2 C8 C9 C10 -87.88(17) O3 C3 C2 C1 -100.57(15) O3 C3 C2 C7 144.99(13) O3 C3 C2 C19 19.18(18) O4 C7 C2 C1 153.39(13) O4 C7 C2 C3 -84.48(16) O4 C7 C2 C19 41.47(18) O4 C7 C6 C5 57.37(15) O4 C7 C6 C11 -63.56(15) O4 C7 C6 C20 175.65(13) O4 C7 C8 C9 77.35(16) O4 C7 C8 O2 -157.97(11)