#------------------------------------------------------------------------------ #$Date: 2020-01-30 02:10:32 +0200 (Thu, 30 Jan 2020) $ #$Revision: 247355 $ #$URL: file:///home/coder/svn-repositories/cod/cif/1/55/71/1557187.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_1557187 loop_ _publ_author_name 'Liu, Tingting' 'Wu, Haibo' 'Zhang, Jing' 'Deng, Wenjie' 'Yang, Luowenlei' _publ_section_title ; Modified Eremophilanes from Parasenecio hastatus and Their Neuroprotective Activities ; _journal_name_full 'Journal of Natural Products' _journal_paper_doi 10.1021/acs.jnatprod.9b00217 _journal_year 2020 _chemical_formula_moiety 'C15 H14 O5, H2 O' _chemical_formula_sum 'C15 H16 O6' _chemical_formula_weight 292.28 _space_group_crystal_system monoclinic _space_group_IT_number 14 _space_group_name_Hall '-P 2ybc' _space_group_name_H-M_alt 'P 1 21/c 1' _atom_sites_solution_hydrogens geom _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _audit_creation_date 2018-01-12 _audit_creation_method ; Olex2 1.1 (compiled 2011.02.15 svn.r1672, GUI svn.r3494) ; _cell_angle_alpha 90.00 _cell_angle_beta 96.612(2) _cell_angle_gamma 90.00 _cell_formula_units_Z 4 _cell_length_a 6.20271(18) _cell_length_b 12.9748(4) _cell_length_c 17.3444(4) _cell_measurement_reflns_used 5667 _cell_measurement_temperature 108.00(14) _cell_measurement_theta_max 71.0050 _cell_measurement_theta_min 6.1600 _cell_volume 1386.57(7) _computing_cell_refinement ; CrysAlisPro, Agilent Technologies, Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET) (compiled Aug 13 2014,18:06:01) ; _computing_data_collection ; CrysAlisPro, Agilent Technologies, Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET) (compiled Aug 13 2014,18:06:01) ; _computing_data_reduction ; CrysAlisPro, Agilent Technologies, Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET) (compiled Aug 13 2014,18:06:01) ; _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)/Bruker' _diffrn_ambient_environment N~2~ _diffrn_ambient_temperature 108.00(14) _diffrn_detector 'CCD plate' _diffrn_detector_area_resol_mean 16.0971 _diffrn_detector_type Eos _diffrn_measured_fraction_theta_full 0.9985 _diffrn_measured_fraction_theta_max 0.9894 _diffrn_measurement_details ; #__ type_ start__ end____ width___ exp.time_ 1 omega 28.00 97.00 1.0000 1.0000 omega____ theta____ kappa____ phi______ frames - 36.7919 37.0000 0.0000 69 #__ type_ start__ end____ width___ exp.time_ 2 omega 63.00 88.00 1.0000 1.0000 omega____ theta____ kappa____ phi______ frames - 36.7919 37.0000 30.0000 25 #__ type_ start__ end____ width___ exp.time_ 3 omega 50.00 76.00 1.0000 1.0000 omega____ theta____ kappa____ phi______ frames - 36.7919 19.0000 -30.0000 26 #__ type_ start__ end____ width___ exp.time_ 4 omega 67.00 92.00 1.0000 1.0000 omega____ theta____ kappa____ phi______ frames - 36.7919 37.0000 -60.0000 25 #__ type_ start__ end____ width___ exp.time_ 5 omega 91.00 117.00 1.0000 1.8000 omega____ theta____ kappa____ phi______ frames - 108.0000 45.0000 0.0000 26 #__ type_ start__ end____ width___ exp.time_ 6 omega 95.00 140.00 1.0000 1.8000 omega____ theta____ kappa____ phi______ frames - 108.0000 45.0000 -30.0000 45 #__ type_ start__ end____ width___ exp.time_ 7 omega 115.00 176.00 1.0000 1.8000 omega____ theta____ kappa____ phi______ frames - 108.0000 77.0000 -30.0000 61 #__ type_ start__ end____ width___ exp.time_ 8 omega 139.00 165.00 1.0000 1.8000 omega____ theta____ kappa____ phi______ frames - 108.0000 77.0000 -120.0000 26 #__ type_ start__ end____ width___ exp.time_ 9 omega 129.00 176.00 1.0000 1.8000 omega____ theta____ kappa____ phi______ frames - 108.0000 77.0000 -90.0000 47 #__ type_ start__ end____ width___ exp.time_ 10 omega 117.00 176.00 1.0000 1.8000 omega____ theta____ kappa____ phi______ frames - 108.0000 77.0000 30.0000 59 #__ type_ start__ end____ width___ exp.time_ 11 omega 97.00 123.00 1.0000 1.8000 omega____ theta____ kappa____ phi______ frames - 108.0000 45.0000 -60.0000 26 #__ type_ start__ end____ width___ exp.time_ 12 omega 94.00 122.00 1.0000 1.8000 omega____ theta____ kappa____ phi______ frames - 108.0000 61.0000 -90.0000 28 #__ type_ start__ end____ width___ exp.time_ 13 omega 94.00 120.00 1.0000 1.8000 omega____ theta____ kappa____ phi______ frames - 108.0000 45.0000 -90.0000 26 #__ type_ start__ end____ width___ exp.time_ 14 omega 87.00 120.00 1.0000 1.8000 omega____ theta____ kappa____ phi______ frames - 108.0000 30.0000 -60.0000 33 #__ type_ start__ end____ width___ exp.time_ 15 omega 89.00 115.00 1.0000 1.8000 omega____ theta____ kappa____ phi______ frames - 108.0000 30.0000 0.0000 26 #__ type_ start__ end____ width___ exp.time_ 16 omega 93.00 119.00 1.0000 1.8000 omega____ theta____ kappa____ phi______ frames - 108.0000 61.0000 0.0000 26 #__ type_ start__ end____ width___ exp.time_ 17 omega 91.00 117.00 1.0000 1.8000 omega____ theta____ kappa____ phi______ frames - 108.0000 61.0000 -30.0000 26 #__ type_ start__ end____ width___ exp.time_ 18 omega 90.00 122.00 1.0000 1.8000 omega____ theta____ kappa____ phi______ frames - 108.0000 61.0000 -60.0000 32 #__ type_ start__ end____ width___ exp.time_ 19 omega 87.00 113.00 1.0000 1.8000 omega____ theta____ kappa____ phi______ frames - 108.0000 30.0000 -30.0000 26 #__ type_ start__ end____ width___ exp.time_ 20 omega 81.00 155.00 1.0000 1.8000 omega____ theta____ kappa____ phi______ frames - 108.0000 77.0000 0.0000 74 #__ type_ start__ end____ width___ exp.time_ 21 omega 101.00 167.00 1.0000 1.8000 omega____ theta____ kappa____ phi______ frames - 108.0000 156.0000 -101.0000 66 #__ type_ start__ end____ width___ exp.time_ 22 omega 106.00 177.00 1.0000 1.8000 omega____ theta____ kappa____ phi______ frames - 108.0000 111.0000 -150.0000 71 #__ type_ start__ end____ width___ exp.time_ 23 omega 89.00 114.00 1.0000 1.8000 omega____ theta____ kappa____ phi______ frames - 108.0000 30.0000 30.0000 25 #__ type_ start__ end____ width___ exp.time_ 24 omega 81.00 107.00 1.0000 1.8000 omega____ theta____ kappa____ phi______ frames - 108.0000 77.0000 -30.0000 26 #__ type_ start__ end____ width___ exp.time_ 25 omega 81.00 107.00 1.0000 1.8000 omega____ theta____ kappa____ phi______ frames - 108.0000 77.0000 -60.0000 26 #__ type_ start__ end____ width___ exp.time_ 26 omega 81.00 107.00 1.0000 1.8000 omega____ theta____ kappa____ phi______ frames - 108.0000 77.0000 -90.0000 26 #__ type_ start__ end____ width___ exp.time_ 27 omega 81.00 107.00 1.0000 1.8000 omega____ theta____ kappa____ phi______ frames - 108.0000 77.0000 -120.0000 26 #__ type_ start__ end____ width___ exp.time_ 28 omega 58.00 83.00 1.0000 1.0000 omega____ theta____ kappa____ phi______ frames - 36.7919 178.0000 -60.0000 25 #__ type_ start__ end____ width___ exp.time_ 29 omega 65.00 92.00 1.0000 1.0000 omega____ theta____ kappa____ phi______ frames - 36.7919 178.0000 60.0000 27 #__ type_ start__ end____ width___ exp.time_ 30 omega 19.00 44.00 1.0000 1.0000 omega____ theta____ kappa____ phi______ frames - 36.7919 77.0000 0.0000 25 #__ type_ start__ end____ width___ exp.time_ 31 omega 18.00 106.00 1.0000 1.0000 omega____ theta____ kappa____ phi______ frames - 36.7919 37.0000 60.0000 88 #__ type_ start__ end____ width___ exp.time_ 32 omega 40.00 77.00 1.0000 1.8000 omega____ theta____ kappa____ phi______ frames - 108.0000 -30.0000 -90.0000 37 #__ type_ start__ end____ width___ exp.time_ 33 omega 52.00 78.00 1.0000 1.8000 omega____ theta____ kappa____ phi______ frames - 108.0000 -45.0000 -120.0000 26 #__ type_ start__ end____ width___ exp.time_ 34 omega 53.00 113.00 1.0000 1.8000 omega____ theta____ kappa____ phi______ frames - 108.0000 -61.0000 -120.0000 60 #__ type_ start__ end____ width___ exp.time_ 35 omega 44.00 94.00 1.0000 1.8000 omega____ theta____ kappa____ phi______ frames - 108.0000 -94.0000 -180.0000 50 #__ type_ start__ end____ width___ exp.time_ 36 omega 39.00 103.00 1.0000 1.8000 omega____ theta____ kappa____ phi______ frames - 108.0000 -94.0000 -120.0000 64 #__ type_ start__ end____ width___ exp.time_ 37 omega 62.00 109.00 1.0000 1.0000 omega____ theta____ kappa____ phi______ frames - 36.7919 -178.0000 -90.0000 47 #__ type_ start__ end____ width___ exp.time_ 38 omega -4.00 75.00 1.0000 1.0000 omega____ theta____ kappa____ phi______ frames - 36.7919 -99.0000 120.0000 79 #__ type_ start__ end____ width___ exp.time_ 39 omega 25.00 53.00 1.0000 1.0000 omega____ theta____ kappa____ phi______ frames - 36.7919 -19.0000 90.0000 28 #__ type_ start__ end____ width___ exp.time_ 40 omega -10.00 15.00 1.0000 1.0000 omega____ theta____ kappa____ phi______ frames - 36.7919 -19.0000 90.0000 25 #__ type_ start__ end____ width___ exp.time_ 41 omega -31.00 64.00 1.0000 1.0000 omega____ theta____ kappa____ phi______ frames - 36.7919 -77.0000 -90.0000 95 #__ type_ start__ end____ width___ exp.time_ 42 omega -28.00 24.00 1.0000 1.0000 omega____ theta____ kappa____ phi______ frames - 36.7919 -57.0000 -180.0000 52 ; _diffrn_measurement_device 'four-circle diffractometer' _diffrn_measurement_device_type 'Xcalibur, Eos, Gemini' _diffrn_measurement_method '\w scans' _diffrn_orient_matrix_UB_11 0.1792873000 _diffrn_orient_matrix_UB_12 -0.0661208000 _diffrn_orient_matrix_UB_13 0.0446285000 _diffrn_orient_matrix_UB_21 -0.0922122000 _diffrn_orient_matrix_UB_22 0.0246074000 _diffrn_orient_matrix_UB_23 0.0766918000 _diffrn_orient_matrix_UB_31 -0.1477872000 _diffrn_orient_matrix_UB_32 -0.0955205000 _diffrn_orient_matrix_UB_33 -0.0111333000 _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 0.0284 _diffrn_reflns_av_unetI/netI 0.0216 _diffrn_reflns_limit_h_max 5 _diffrn_reflns_limit_h_min -7 _diffrn_reflns_limit_k_max 15 _diffrn_reflns_limit_k_min -15 _diffrn_reflns_limit_l_max 21 _diffrn_reflns_limit_l_min -21 _diffrn_reflns_number 11102 _diffrn_reflns_theta_full 71.12 _diffrn_reflns_theta_max 71.12 _diffrn_reflns_theta_min 4.27 _diffrn_source 'Enhance (Cu) X-ray Source' _exptl_absorpt_coefficient_mu 0.918 _exptl_absorpt_correction_T_max 1.00000 _exptl_absorpt_correction_T_min 0.71604 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details ; CrysAlisPro, Agilent Technologies, Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET) (compiled Aug 13 2014,18:06:01) Empirical absorption correction using spherical harmonics, implemented in SCALE3 ABSPACK scaling algorithm. ; _exptl_crystal_density_diffrn 1.400 _exptl_crystal_density_method 'not measured' _exptl_crystal_description ; ; _exptl_crystal_F_000 616 _exptl_crystal_size_max 0.40 _exptl_crystal_size_mid 0.36 _exptl_crystal_size_min 0.11 _refine_diff_density_max 0.360 _refine_diff_density_min -0.226 _refine_diff_density_rms 0.051 _refine_ls_extinction_coef 0.0047(5) _refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^ _refine_ls_extinction_method SHELXL _refine_ls_goodness_of_fit_ref 1.051 _refine_ls_hydrogen_treatment mixed _refine_ls_matrix_type full _refine_ls_number_parameters 201 _refine_ls_number_reflns 2669 _refine_ls_number_restraints 3 _refine_ls_restrained_S_all 1.050 _refine_ls_R_factor_all 0.0408 _refine_ls_R_factor_gt 0.0385 _refine_ls_shift/su_max 0.001 _refine_ls_shift/su_mean 0.000 _refine_ls_structure_factor_coef Fsqd _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0536P)^2^+0.6658P] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_gt 0.0995 _refine_ls_wR_factor_ref 0.1014 _reflns_number_gt 2496 _reflns_number_total 2669 _reflns_threshold_expression >2sigma(I) _cod_data_source_file np9b00217_si_001.cif _cod_data_source_block exp_5321 _cod_original_cell_volume 1386.58(6) _cod_database_code 1557187 _reflns_odcompleteness_completeness 99.85 _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, y+1/2, -z+1/2' 3 '-x, -y, -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 O2 O 0.29338(15) 0.63781(7) 0.29437(5) 0.0170(2) Uani 1 1 d . O3 O 0.72906(16) 0.72425(8) 0.27073(6) 0.0224(2) Uani 1 1 d . O1 O 0.34790(17) 0.65605(8) 0.42350(6) 0.0222(2) Uani 1 1 d . O5 O 0.73348(17) 0.66057(8) 0.02848(6) 0.0233(3) Uani 1 1 d . H5 H 0.7875 0.6998 -0.0010 0.035 Uiso 1 1 calc R O4 O 0.72719(16) 0.75202(8) 0.14370(6) 0.0212(2) Uani 1 1 d . O6 O 0.91532(17) 0.72448(10) 0.42688(6) 0.0292(3) Uani 1 1 d D C13 C 0.6544(2) 0.39247(11) 0.17017(8) 0.0198(3) Uani 1 1 d . H13A H 0.5218 0.3565 0.1537 0.030 Uiso 1 1 calc R H13B H 0.7757 0.3485 0.1639 0.030 Uiso 1 1 calc R H13C H 0.6626 0.4534 0.1393 0.030 Uiso 1 1 calc R C9 C 0.4678(2) 0.63713(10) 0.17719(7) 0.0136(3) Uani 1 1 d . C3 C 0.6834(2) 0.47847(11) 0.41439(8) 0.0194(3) Uani 1 1 d . H3 H 0.6905 0.4974 0.4663 0.023 Uiso 1 1 calc R C4 C 0.8118(2) 0.39988(11) 0.38977(8) 0.0209(3) Uani 1 1 d . H4 H 0.9077 0.3651 0.4259 0.025 Uiso 1 1 calc R C10 C 0.6515(2) 0.70636(10) 0.20525(8) 0.0159(3) Uani 1 1 d . C15 C 0.2776(2) 0.59523(12) 0.03916(8) 0.0209(3) Uani 1 1 d . H15A H 0.3152 0.5240 0.0337 0.031 Uiso 1 1 calc R H15B H 0.2829 0.6300 -0.0094 0.031 Uiso 1 1 calc R H15C H 0.1337 0.6001 0.0541 0.031 Uiso 1 1 calc R C14 C 0.1646(2) 0.51115(11) 0.19968(8) 0.0212(3) Uani 1 1 d . H14A H 0.1075 0.4724 0.2399 0.032 Uiso 1 1 calc R H14B H 0.2028 0.4650 0.1602 0.032 Uiso 1 1 calc R H14C H 0.0568 0.5590 0.1774 0.032 Uiso 1 1 calc R C7 C 0.5315(2) 0.50091(10) 0.27986(8) 0.0141(3) Uani 1 1 d . C1 C 0.3917(2) 0.61227(10) 0.36551(8) 0.0170(3) Uani 1 1 d . C2 C 0.5439(2) 0.52731(10) 0.35735(8) 0.0162(3) Uani 1 1 d . C8 C 0.3651(2) 0.56995(10) 0.23385(7) 0.0144(3) Uani 1 1 d . C12 C 0.6032(2) 0.71562(11) 0.07272(8) 0.0177(3) Uani 1 1 d . H12 H 0.5338 0.7733 0.0430 0.021 Uiso 1 1 calc R C6 C 0.6592(2) 0.42218(10) 0.25409(8) 0.0156(3) Uani 1 1 d . C11 C 0.4350(2) 0.64437(10) 0.09996(8) 0.0144(3) Uani 1 1 d . C5 C 0.7985(2) 0.37269(10) 0.31166(8) 0.0187(3) Uani 1 1 d . H5A H 0.8857 0.3194 0.2972 0.022 Uiso 1 1 calc R H6A H 1.0481(16) 0.7076(14) 0.4255(10) 0.028 Uiso 1 1 d D H6B H 0.854(3) 0.7224(15) 0.3805(6) 0.028 Uiso 1 1 d 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 O2 0.0169(5) 0.0198(5) 0.0154(5) 0.0014(4) 0.0060(4) 0.0051(4) O3 0.0225(5) 0.0251(5) 0.0185(5) -0.0012(4) -0.0026(4) -0.0054(4) O1 0.0261(5) 0.0254(5) 0.0162(5) -0.0006(4) 0.0077(4) 0.0057(4) O5 0.0230(5) 0.0242(5) 0.0253(5) 0.0038(4) 0.0137(4) 0.0021(4) O4 0.0202(5) 0.0234(5) 0.0203(5) 0.0028(4) 0.0030(4) -0.0073(4) O6 0.0198(5) 0.0487(7) 0.0193(5) -0.0097(5) 0.0025(4) 0.0060(5) C13 0.0222(7) 0.0170(7) 0.0213(7) -0.0027(5) 0.0065(5) 0.0011(5) C9 0.0111(6) 0.0134(6) 0.0164(6) -0.0006(5) 0.0020(5) 0.0018(5) C3 0.0207(7) 0.0217(7) 0.0160(6) 0.0042(5) 0.0035(5) -0.0009(5) C4 0.0190(7) 0.0206(7) 0.0232(7) 0.0092(6) 0.0020(5) 0.0019(5) C10 0.0144(6) 0.0146(6) 0.0191(7) 0.0017(5) 0.0029(5) -0.0004(5) C15 0.0183(7) 0.0289(7) 0.0151(6) -0.0012(5) 0.0002(5) 0.0001(5) C14 0.0144(7) 0.0265(7) 0.0229(7) 0.0021(6) 0.0035(5) -0.0052(5) C7 0.0131(6) 0.0132(6) 0.0164(6) 0.0030(5) 0.0042(5) -0.0030(5) C1 0.0165(6) 0.0181(7) 0.0173(7) 0.0031(5) 0.0057(5) -0.0003(5) C2 0.0162(6) 0.0157(6) 0.0177(6) 0.0021(5) 0.0066(5) -0.0014(5) C8 0.0129(6) 0.0157(6) 0.0155(6) -0.0002(5) 0.0049(5) 0.0005(5) C12 0.0184(7) 0.0187(7) 0.0163(6) 0.0028(5) 0.0038(5) 0.0003(5) C6 0.0144(6) 0.0129(6) 0.0206(7) 0.0006(5) 0.0064(5) -0.0032(5) C11 0.0128(6) 0.0143(6) 0.0165(6) 0.0008(5) 0.0033(5) 0.0040(5) C5 0.0165(6) 0.0138(6) 0.0270(7) 0.0037(5) 0.0078(5) 0.0008(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 C1 O2 C8 111.17(10) C12 O5 H5 109.5 C10 O4 C12 109.19(10) H6A O6 H6B 107.1(15) H13A C13 H13B 109.5 H13A C13 H13C 109.5 H13B C13 H13C 109.5 C6 C13 H13A 109.5 C6 C13 H13B 109.5 C6 C13 H13C 109.5 C10 C9 C8 120.04(11) C11 C9 C10 107.95(11) C11 C9 C8 131.88(12) C4 C3 H3 121.7 C2 C3 H3 121.7 C2 C3 C4 116.57(13) C3 C4 H4 119.6 C3 C4 C5 120.81(13) C5 C4 H4 119.6 O3 C10 O4 121.54(12) O3 C10 C9 129.25(12) O4 C10 C9 109.20(11) H15A C15 H15B 109.5 H15A C15 H15C 109.5 H15B C15 H15C 109.5 C11 C15 H15A 109.5 C11 C15 H15B 109.5 C11 C15 H15C 109.5 H14A C14 H14B 109.5 H14A C14 H14C 109.5 H14B C14 H14C 109.5 C8 C14 H14A 109.5 C8 C14 H14B 109.5 C8 C14 H14C 109.5 C2 C7 C8 108.85(11) C2 C7 C6 121.50(12) C6 C7 C8 129.65(12) O2 C1 C2 108.86(11) O1 C1 O2 121.41(12) O1 C1 C2 129.72(13) C3 C2 C1 128.91(13) C7 C2 C3 122.70(12) C7 C2 C1 108.39(12) O2 C8 C9 107.63(10) O2 C8 C14 106.05(10) O2 C8 C7 102.69(10) C9 C8 C14 115.08(11) C9 C8 C7 111.73(10) C14 C8 C7 112.59(11) O5 C12 O4 110.71(11) O5 C12 H12 110.8 O5 C12 C11 109.14(11) O4 C12 H12 110.8 O4 C12 C11 104.55(10) C11 C12 H12 110.8 C7 C6 C13 123.26(12) C7 C6 C5 115.70(12) C5 C6 C13 121.03(12) C9 C11 C15 133.60(12) C9 C11 C12 109.04(12) C15 C11 C12 117.32(12) C4 C5 C6 122.72(13) C4 C5 H5A 118.6 C6 C5 H5A 118.6 loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance O2 C1 1.3529(17) O2 C8 1.4774(15) O3 C10 1.2039(17) O1 C1 1.2128(17) O5 H5 0.8200 O5 C12 1.3764(17) O4 C10 1.3515(16) O4 C12 1.4532(17) O6 H6A 0.855(9) O6 H6B 0.851(9) C13 H13A 0.9600 C13 H13B 0.9600 C13 H13C 0.9600 C13 C6 1.5027(19) C9 C10 1.4882(18) C9 C8 1.5084(17) C9 C11 1.3347(18) C3 H3 0.9300 C3 C4 1.391(2) C3 C2 1.3899(19) C4 H4 0.9300 C4 C5 1.393(2) C15 H15A 0.9600 C15 H15B 0.9600 C15 H15C 0.9600 C15 C11 1.4947(18) C14 H14A 0.9600 C14 H14B 0.9600 C14 H14C 0.9600 C14 C8 1.5199(18) C7 C2 1.3806(19) C7 C8 1.5214(17) C7 C6 1.3974(18) C1 C2 1.4689(18) C12 H12 0.9800 C12 C11 1.5101(18) C6 C5 1.399(2) C5 H5A 0.9300 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 O2 C1 C2 C3 178.06(13) O2 C1 C2 C7 -1.26(15) O1 C1 C2 C3 -3.0(2) O1 C1 C2 C7 177.68(14) O5 C12 C11 C9 115.51(12) O5 C12 C11 C15 -62.49(15) O4 C12 C11 C9 -2.96(14) O4 C12 C11 C15 179.03(11) C13 C6 C5 C4 178.24(12) C3 C4 C5 C6 0.5(2) C4 C3 C2 C7 -0.4(2) C4 C3 C2 C1 -179.58(13) C10 O4 C12 O5 -115.22(12) C10 O4 C12 C11 2.19(14) C10 C9 C8 O2 55.96(14) C10 C9 C8 C14 173.92(11) C10 C9 C8 C7 -56.06(15) C10 C9 C11 C15 -179.90(13) C10 C9 C11 C12 2.55(14) C7 C6 C5 C4 -0.51(19) C1 O2 C8 C9 -120.17(11) C1 O2 C8 C14 116.18(12) C1 O2 C8 C7 -2.15(13) C2 C3 C4 C5 -0.1(2) C2 C7 C8 O2 1.31(13) C2 C7 C8 C9 116.40(12) C2 C7 C8 C14 -112.30(12) C2 C7 C6 C13 -178.64(12) C2 C7 C6 C5 0.08(18) C8 O2 C1 O1 -176.88(12) C8 O2 C1 C2 2.17(14) C8 C9 C10 O3 -5.7(2) C8 C9 C10 O4 175.03(11) C8 C9 C11 C15 4.5(2) C8 C9 C11 C12 -173.05(12) C8 C7 C2 C3 -179.50(12) C8 C7 C2 C1 -0.13(14) C8 C7 C6 C13 1.2(2) C8 C7 C6 C5 179.90(12) C12 O4 C10 O3 179.89(12) C12 O4 C10 C9 -0.76(14) C6 C7 C2 C3 0.4(2) C6 C7 C2 C1 179.72(11) C6 C7 C8 O2 -178.52(12) C6 C7 C8 C9 -63.44(17) C6 C7 C8 C14 67.87(17) C11 C9 C10 O3 178.09(14) C11 C9 C10 O4 -1.19(15) C11 C9 C8 O2 -128.88(14) C11 C9 C8 C14 -10.9(2) C11 C9 C8 C7 119.10(15)