#------------------------------------------------------------------------------ #$Date: 2016-02-14 06:40:26 +0200 (Sun, 14 Feb 2016) $ #$Revision: 176432 $ #$URL: file:///home/coder/svn-repositories/cod/cif/1/51/84/1518457.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_1518457 loop_ _publ_author_name 'Lan, Ping' 'Banwell, Martin G.' 'Willis, Anthony C.' _publ_section_title ; Chemoenzymatic Synthesis of the Enantiomer of 4,12-Dihydroxysterpurene, the Structure Assigned to a Metabolite Isolated from the Culture Broth of Stereum purpureum. ; _journal_issue 1 _journal_name_full 'Organic letters' _journal_page_first 166 _journal_page_last 169 _journal_paper_doi 10.1021/ol5034817 _journal_volume 17 _journal_year 2015 _chemical_absolute_configuration ad _chemical_compound_source local _chemical_formula_moiety 'C21 H28 O4' _chemical_formula_sum 'C21 H28 O4' _chemical_formula_weight 344.45 _space_group_IT_number 19 _symmetry_cell_setting orthorhombic _symmetry_space_group_name_Hall 'P 2ac 2ab' _symmetry_space_group_name_H-M 'P 21 21 21' _atom_sites_solution_hydrogens difmap _atom_sites_solution_primary direct _audit_creation_date 14-10-30 _audit_creation_method CRYSTALS_ver_14.40 _audit_update_record ; 2014-10-30 - Report on C21 H28 O4 by Anthony C. Willis for Ping Lan and Martin Banwell 2014-10-30 - passes checkcif tests ; _cell_angle_alpha 90 _cell_angle_beta 90 _cell_angle_gamma 90 _cell_formula_units_Z 4 _cell_length_a 6.2688(1) _cell_length_b 16.3080(1) _cell_length_c 18.2849(2) _cell_measurement_reflns_used 16374 _cell_measurement_temperature 150 _cell_measurement_theta_max 72 _cell_measurement_theta_min 4 _cell_volume 1869.29(4) _computing_cell_refinement ; CrysAlisPro ; _computing_data_collection ; CrysAlisPro, Agilent Technologies, Version 1.171.37.33d (release 23-04-2014 CrysAlis171 .NET) (compiled Apr 23 2014,17:37:27) ; _computing_data_reduction ; CrysAlisPro ; _computing_molecular_graphics 'PLATON (Spek, 2008)' _computing_publication_material 'CRYSTALS (Betteridge et al., 2003)' _computing_structure_refinement 'CRYSTALS (Betteridge et al., 2003)' _computing_structure_solution 'SIR92 (Altomare et al., 1994)' _diffrn_ambient_temperature 150 _diffrn_measured_fraction_theta_full 1.000 _diffrn_measured_fraction_theta_max 1.000 _diffrn_measurement_device Area _diffrn_measurement_device_type 'SuperNova, Dual, Cu at zero, EosS2' _diffrn_measurement_method \w _diffrn_radiation_monochromator mirror _diffrn_radiation_source 'Supernova (Cu) X-ray Source' _diffrn_radiation_type 'Cu K\a' _diffrn_radiation_wavelength 1.54180 _diffrn_reflns_av_R_equivalents 0.028 _diffrn_reflns_limit_h_max 7 _diffrn_reflns_limit_h_min -7 _diffrn_reflns_limit_k_max 20 _diffrn_reflns_limit_k_min -18 _diffrn_reflns_limit_l_max 22 _diffrn_reflns_limit_l_min -21 _diffrn_reflns_number 22540 _diffrn_reflns_theta_full 71.931 _diffrn_reflns_theta_max 71.931 _diffrn_reflns_theta_min 3.632 _diffrn_standards_number 0 _exptl_absorpt_coefficient_mu 0.668 _exptl_absorpt_correction_T_max 0.93 _exptl_absorpt_correction_T_min 0.87 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details ; CrysAlisPro, Agilent Technologies, Version 1.171.37.33d (release 23-04-2014 CrysAlis171 .NET) (compiled Apr 23 2014,17:37:27) Empirical absorption correction using spherical harmonics, implemented in SCALE3 ABSPACK scaling algorithm. ; _exptl_crystal_colour colourless _exptl_crystal_density_diffrn 1.224 _exptl_crystal_density_method 'not measured' _exptl_crystal_description block _exptl_crystal_F_000 744 _exptl_crystal_size_max 0.259 _exptl_crystal_size_mid 0.144 _exptl_crystal_size_min 0.112 _refine_diff_density_max 0.15 _refine_diff_density_min -0.13 _refine_ls_abs_structure_details 'Flack (1983), 1540 Friedel-pairs' _refine_ls_abs_structure_Flack -0.05(11) _refine_ls_extinction_method None _refine_ls_goodness_of_fit_ref 1.0050 _refine_ls_hydrogen_treatment refxyz _refine_ls_matrix_type full _refine_ls_number_parameters 311 _refine_ls_number_reflns 3675 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0257 _refine_ls_R_factor_gt 0.0252 _refine_ls_shift/su_max 0.0040108 _refine_ls_shift/su_mean 0.0004407 _refine_ls_structure_factor_coef Fsqd _refine_ls_weighting_details ; Method= Modified Sheldrick w=1/[\s^2^(F^2^) + ( 0.04P)^2^ + 0.29P] ,where P=(max(Fo^2^,0) + 2Fc^2^)/3 ; _refine_ls_weighting_scheme calc _refine_ls_wR_factor_all 0.0656 _refine_ls_wR_factor_gt 0.0651 _refine_ls_wR_factor_ref 0.0656 _reflns_limit_h_max 7 _reflns_limit_h_min -7 _reflns_limit_k_max 20 _reflns_limit_k_min 0 _reflns_limit_l_max 22 _reflns_limit_l_min 0 _reflns_number_gt 3603 _reflns_number_total 3675 _reflns_threshold_expression I>2.0\s(I) _oxford_diffrn_Wilson_B_factor 2.10 _oxford_diffrn_Wilson_scale 0.03 _oxford_refine_ls_r_factor_ref 0.0257 _oxford_refine_ls_scale 5.89(9) _oxford_reflns_number_all 3675 _oxford_reflns_threshold_expression_ref I>-10.0\s(I) _oxford_structure_analysis_title 'Z:\ban1456SN\Tony_ban1456SN_data At 15:14 on' _cod_data_source_file ol5034817_si_003.cif _cod_data_source_block ban1456SN _cod_depositor_comments 'Adding full bibliography for 1518456--1518457.cif.' _cod_original_sg_symbol_Hall 'P 2ac 2ab ' _cod_original_sg_symbol_H-M 'P 21 21 21 ' _cod_database_code 1518457 #BEGIN Tags that were not found in dictionaries: _iucr_refine_instruction_details_constraints ; BLOCK CONT SCALE CONT C ( 1 ,X'S,U'S) UNTIL C ( 25 ) CONT H ( 21 ,X'S) UNTIL H ( 253 ) CONT ENANTIO END ; _iucr_refine_instruction_details_restraints ; NO REM HREST START (DO NOT REMOVE THIS LINE) REM HREST END (DO NOT REMOVE THIS LINE) END ; #END Tags that were not found in dictionaries loop_ _symmetry_equiv_pos_as_xyz x,y,z x+1/2,-y+1/2,-z -x,y+1/2,-z+1/2 -x+1/2,-y,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_occupancy _atom_site_adp_type C1 C 0.45850(17) 0.14150(6) 0.41276(5) 0.0179 1.0000 Uani C2 C 0.39632(17) 0.22937(6) 0.43066(5) 0.0173 1.0000 Uani C3 C 0.52530(17) 0.29160(6) 0.38523(5) 0.0187 1.0000 Uani C4 C 0.38277(18) 0.35946(6) 0.35172(6) 0.0213 1.0000 Uani C5 C 0.40677(19) 0.31987(7) 0.27609(6) 0.0236 1.0000 Uani C6 C 0.59330(18) 0.26646(6) 0.30524(5) 0.0204 1.0000 Uani C7 C 0.59157(19) 0.17488(6) 0.28586(6) 0.0220 1.0000 Uani C8 C 0.43059(18) 0.12636(6) 0.33029(6) 0.0195 1.0000 Uani C9 C 0.4404(2) 0.03290(6) 0.32518(6) 0.0227 1.0000 Uani C10 C 0.31280(18) 0.00158(6) 0.39248(6) 0.0214 1.0000 Uani C11 C 0.31798(18) 0.07511(6) 0.44743(6) 0.0211 1.0000 Uani O12 O 0.68075(13) 0.12961(5) 0.43095(4) 0.0218 1.0000 Uani O13 O 0.42924(13) 0.24296(5) 0.50687(4) 0.0205 1.0000 Uani O14 O 0.48804(13) 0.43917(4) 0.35188(4) 0.0234 1.0000 Uani C15 C 0.43495(19) 0.49157(6) 0.40469(6) 0.0225 1.0000 Uani C16 C 0.56274(19) 0.56883(6) 0.40100(6) 0.0234 1.0000 Uani C17 C 0.75845(19) 0.57213(7) 0.36534(6) 0.0279 1.0000 Uani C18 C 0.8724(2) 0.64539(9) 0.36373(7) 0.0368 1.0000 Uani C19 C 0.7905(3) 0.71479(8) 0.39715(7) 0.0393 1.0000 Uani C20 C 0.5967(3) 0.71160(7) 0.43322(7) 0.0371 1.0000 Uani C21 C 0.4825(2) 0.63858(7) 0.43559(7) 0.0299 1.0000 Uani O22 O 0.29766(16) 0.47951(5) 0.44995(5) 0.0342 1.0000 Uani C23 C 0.8101(2) 0.30283(8) 0.28569(7) 0.0286 1.0000 Uani C24 C 0.0823(2) -0.01763(8) 0.37129(7) 0.0334 1.0000 Uani C25 C 0.4172(2) -0.07509(7) 0.42440(6) 0.0300 1.0000 Uani H21 H 0.239(2) 0.2328(8) 0.4190(7) 0.0187 1.0000 Uiso H31 H 0.647(2) 0.3108(8) 0.4153(7) 0.0214 1.0000 Uiso H41 H 0.240(2) 0.3645(8) 0.3716(7) 0.0228 1.0000 Uiso H51 H 0.435(2) 0.3564(8) 0.2352(8) 0.0280 1.0000 Uiso H52 H 0.282(2) 0.2866(9) 0.2655(8) 0.0295 1.0000 Uiso H71 H 0.734(2) 0.1515(8) 0.2967(8) 0.0256 1.0000 Uiso H72 H 0.560(2) 0.1701(8) 0.2337(8) 0.0259 1.0000 Uiso H81 H 0.278(2) 0.1450(8) 0.3167(7) 0.0219 1.0000 Uiso H91 H 0.591(2) 0.0149(8) 0.3291(8) 0.0257 1.0000 Uiso H92 H 0.378(2) 0.0122(9) 0.2787(8) 0.0261 1.0000 Uiso H111 H 0.371(2) 0.0605(8) 0.4982(8) 0.0258 1.0000 Uiso H112 H 0.171(2) 0.0963(9) 0.4538(7) 0.0246 1.0000 Uiso H121 H 0.693(3) 0.0978(10) 0.4660(9) 0.0356 1.0000 Uiso H131 H 0.335(3) 0.2802(9) 0.5215(8) 0.0318 1.0000 Uiso H171 H 0.813(3) 0.5230(9) 0.3430(8) 0.0307 1.0000 Uiso H181 H 1.013(3) 0.6468(10) 0.3384(10) 0.0445 1.0000 Uiso H191 H 0.872(3) 0.7676(11) 0.3941(9) 0.0471 1.0000 Uiso H201 H 0.536(3) 0.7611(11) 0.4568(9) 0.0443 1.0000 Uiso H211 H 0.348(3) 0.6359(10) 0.4595(9) 0.0361 1.0000 Uiso H231 H 0.837(3) 0.2931(10) 0.2319(9) 0.0425 1.0000 Uiso H232 H 0.924(3) 0.2761(10) 0.3138(9) 0.0408 1.0000 Uiso H233 H 0.815(3) 0.3616(10) 0.2966(9) 0.0415 1.0000 Uiso H241 H -0.003(3) -0.0303(10) 0.4136(10) 0.0492 1.0000 Uiso H242 H 0.006(3) 0.0310(11) 0.3471(10) 0.0495 1.0000 Uiso H243 H 0.078(3) -0.0634(11) 0.3344(9) 0.0469 1.0000 Uiso H251 H 0.339(3) -0.0966(10) 0.4676(9) 0.0429 1.0000 Uiso H252 H 0.572(3) -0.0633(10) 0.4382(9) 0.0431 1.0000 Uiso H253 H 0.414(3) -0.1200(10) 0.3876(9) 0.0435 1.0000 Uiso 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 0.0217(5) 0.0142(4) 0.0179(5) -0.0006(4) 0.0003(4) 0.0003(4) C2 0.0205(5) 0.0155(4) 0.0158(4) -0.0007(3) 0.0004(4) 0.0001(4) C3 0.0217(5) 0.0152(4) 0.0191(5) 0.0005(4) 0.0009(4) -0.0006(4) C4 0.0248(5) 0.0140(4) 0.0252(5) 0.0023(4) 0.0006(4) -0.0012(4) C5 0.0295(6) 0.0196(5) 0.0218(5) 0.0021(4) -0.0027(4) -0.0018(4) C6 0.0251(5) 0.0175(5) 0.0186(5) 0.0016(4) 0.0024(4) -0.0016(4) C7 0.0298(6) 0.0187(5) 0.0176(5) -0.0007(4) 0.0044(4) 0.0009(4) C8 0.0262(5) 0.0149(4) 0.0173(5) -0.0015(4) 0.0009(4) 0.0003(4) C9 0.0330(6) 0.0151(5) 0.0200(5) -0.0025(4) 0.0020(5) -0.0004(4) C10 0.0283(5) 0.0143(5) 0.0217(5) -0.0020(4) 0.0017(4) -0.0007(4) C11 0.0283(5) 0.0152(4) 0.0198(5) -0.0010(4) 0.0041(4) -0.0020(4) O12 0.0241(4) 0.0182(4) 0.0230(4) 0.0010(3) -0.0014(3) 0.0022(3) O13 0.0267(4) 0.0187(3) 0.0162(3) -0.0022(3) 0.0010(3) 0.0016(3) O14 0.0318(4) 0.0142(3) 0.0241(4) 0.0013(3) 0.0040(3) -0.0021(3) C15 0.0306(6) 0.0166(5) 0.0204(5) 0.0035(4) -0.0006(4) 0.0023(4) C16 0.0351(6) 0.0160(5) 0.0192(5) 0.0036(4) -0.0038(4) 0.0004(4) C17 0.0356(6) 0.0225(5) 0.0257(5) 0.0006(4) -0.0024(5) -0.0031(5) C18 0.0444(8) 0.0338(6) 0.0322(6) 0.0045(5) -0.0022(6) -0.0128(6) C19 0.0632(9) 0.0225(6) 0.0323(6) 0.0058(5) -0.0105(6) -0.0139(6) C20 0.0632(9) 0.0165(5) 0.0315(6) 0.0006(5) -0.0072(6) 0.0019(6) C21 0.0446(7) 0.0192(5) 0.0258(5) 0.0020(4) -0.0022(5) 0.0040(5) O22 0.0435(5) 0.0267(4) 0.0322(4) -0.0026(3) 0.0130(4) -0.0047(4) C23 0.0281(6) 0.0276(6) 0.0301(6) 0.0000(5) 0.0083(5) -0.0047(5) C24 0.0318(6) 0.0312(6) 0.0372(6) -0.0098(5) 0.0013(5) -0.0057(5) C25 0.0453(7) 0.0184(5) 0.0262(6) 0.0031(4) 0.0067(5) 0.0051(5) loop_ _atom_type_symbol _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_Cromer_Mann_a1 _atom_type_scat_Cromer_Mann_b1 _atom_type_scat_Cromer_Mann_a2 _atom_type_scat_Cromer_Mann_b2 _atom_type_scat_Cromer_Mann_a3 _atom_type_scat_Cromer_Mann_b3 _atom_type_scat_Cromer_Mann_a4 _atom_type_scat_Cromer_Mann_b4 _atom_type_scat_Cromer_Mann_c _atom_type_scat_source C 0.0181 0.0091 2.3100 20.8439 1.0200 10.2075 1.5886 0.5687 0.8650 51.6512 0.2156 'International Tables Vol C 4.2.6.8 and 6.1.1.4' H 0.0000 0.0000 0.4930 10.5109 0.3229 26.1257 0.1402 3.1424 0.0408 57.7998 0.0030 'International Tables Vol C 4.2.6.8 and 6.1.1.4' O 0.0492 0.0322 3.0485 13.2771 2.2868 5.7011 1.5463 0.3239 0.8670 32.9089 0.2508 'International Tables Vol C 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 _geom_angle_publ_flag C2 C1 C8 109.46(8) yes C2 C1 C11 115.42(8) yes C8 C1 C11 103.10(8) yes C2 C1 O12 108.91(8) yes C8 C1 O12 108.28(8) yes C11 C1 O12 111.34(8) yes C1 C2 C3 111.73(8) yes C1 C2 O13 108.64(8) yes C3 C2 O13 110.40(8) yes C1 C2 H21 104.9(7) no C3 C2 H21 111.2(7) no O13 C2 H21 109.7(7) no C2 C3 C4 112.41(8) yes C2 C3 C6 118.06(8) yes C4 C3 C6 88.56(8) yes C2 C3 H31 108.3(8) no C4 C3 H31 116.0(8) no C6 C3 H31 112.8(8) no C3 C4 C5 89.97(8) yes C3 C4 O14 112.04(9) yes C5 C4 O14 109.44(8) yes C3 C4 H41 116.4(8) no C5 C4 H41 117.6(8) no O14 C4 H41 110.0(8) no C4 C5 C6 90.02(8) yes C4 C5 H51 117.0(8) no C6 C5 H51 118.0(9) no C4 C5 H52 109.6(8) no C6 C5 H52 111.3(8) no H51 C5 H52 109.6(12) no C5 C6 C3 88.22(8) yes C5 C6 C7 117.47(9) yes C3 C6 C7 117.71(8) yes C5 C6 C23 111.87(9) yes C3 C6 C23 110.92(9) yes C7 C6 C23 109.30(9) yes C6 C7 C8 112.85(9) yes C6 C7 H71 108.8(8) no C8 C7 H71 107.0(8) no C6 C7 H72 107.8(8) no C8 C7 H72 110.1(8) no H71 C7 H72 110.3(12) no C1 C8 C7 111.43(8) yes C1 C8 C9 102.45(8) yes C7 C8 C9 117.42(9) yes C1 C8 H81 107.1(8) no C7 C8 H81 109.5(7) no C9 C8 H81 108.4(7) no C8 C9 C10 105.00(8) yes C8 C9 H91 109.3(8) no C10 C9 H91 109.5(8) no C8 C9 H92 112.1(8) no C10 C9 H92 111.3(8) no H91 C9 H92 109.6(11) no C9 C10 C11 104.24(8) yes C9 C10 C24 110.67(10) yes C11 C10 C24 109.84(9) yes C9 C10 C25 110.57(9) yes C11 C10 C25 111.91(9) yes C24 C10 C25 109.53(10) yes C1 C11 C10 106.71(8) yes C1 C11 H111 110.9(8) no C10 C11 H111 114.5(8) no C1 C11 H112 109.8(8) no C10 C11 H112 108.8(8) no H111 C11 H112 106.0(11) no C1 O12 H121 110.4(12) no C2 O13 H131 107.7(10) no C4 O14 C15 117.42(8) yes O14 C15 C16 111.98(9) yes O14 C15 O22 124.70(10) yes C16 C15 O22 123.31(10) yes C15 C16 C17 121.78(10) yes C15 C16 C21 118.26(11) yes C17 C16 C21 119.95(11) yes C16 C17 C18 119.73(12) yes C16 C17 H171 118.8(9) no C18 C17 H171 121.5(9) no C17 C18 C19 120.09(13) yes C17 C18 H181 118.9(10) no C19 C18 H181 121.0(10) no C18 C19 C20 120.36(12) yes C18 C19 H191 119.1(10) no C20 C19 H191 120.5(10) no C19 C20 C21 119.96(12) yes C19 C20 H201 121.0(10) no C21 C20 H201 119.1(10) no C16 C21 C20 119.90(12) yes C16 C21 H211 119.4(10) no C20 C21 H211 120.7(10) no C6 C23 H231 108.3(10) no C6 C23 H232 110.6(10) no H231 C23 H232 108.7(14) no C6 C23 H233 111.1(10) no H231 C23 H233 110.4(14) no H232 C23 H233 107.8(14) no C10 C24 H241 111.6(11) no C10 C24 H242 113.1(10) no H241 C24 H242 104.5(14) no C10 C24 H243 110.4(10) no H241 C24 H243 111.3(14) no H242 C24 H243 105.7(14) no C10 C25 H251 112.5(10) no C10 C25 H252 110.3(10) no H251 C25 H252 109.8(14) no C10 C25 H253 109.6(10) no H251 C25 H253 105.6(13) no H252 C25 H253 108.8(14) no loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_publ_flag C1 C2 1.5206(13) yes C1 C8 1.5379(14) yes C1 C11 1.5331(14) yes C1 O12 1.4454(13) yes C2 C3 1.5407(13) yes C2 O13 1.4260(12) yes C2 H21 1.012(13) no C3 C4 1.5486(14) yes C3 C6 1.5777(13) yes C3 H31 0.994(14) no C4 C5 1.5336(15) yes C4 O14 1.4579(12) yes C4 H41 0.968(15) no C5 C6 1.5525(16) yes C5 H51 0.973(15) no C5 H52 0.973(15) no C6 C7 1.5349(14) yes C6 C23 1.5255(15) yes C7 C8 1.5181(15) yes C7 H71 0.992(15) no C7 H72 0.977(15) no C8 C9 1.5282(13) yes C8 H81 1.035(15) no C9 C10 1.5539(14) yes C9 H91 0.989(15) no C9 H92 0.995(14) no C10 C11 1.5648(14) yes C10 C24 1.5285(17) yes C10 C25 1.5271(15) yes C11 H111 1.014(14) no C11 H112 0.993(15) no O12 H121 0.827(17) no O13 H131 0.886(16) no O14 C15 1.3315(13) yes C15 C16 1.4947(15) yes C15 O22 1.2101(15) yes C16 C17 1.3904(17) yes C16 C21 1.3953(16) yes C17 C18 1.3925(17) yes C17 H171 0.963(16) no C18 C19 1.385(2) yes C18 H181 0.996(18) no C19 C20 1.383(2) yes C19 H191 1.004(17) no C20 C21 1.3901(18) yes C20 H201 0.991(18) no C21 H211 0.952(17) no C23 H231 1.010(17) no C23 H232 0.981(18) no C23 H233 0.980(17) no C24 H241 0.964(19) no C24 H242 1.026(19) no C24 H243 1.006(18) no C25 H251 0.993(18) no C25 H252 1.023(18) no C25 H253 0.995(18) no loop_ _geom_contact_atom_site_label_1 _geom_contact_atom_site_label_2 _geom_contact_distance _geom_contact_site_symmetry_2 _geom_contact_publ_flag O12 O13 2.7982(11) . no O12 C6 3.2504(12) . no O12 O22 2.9063(12) 2_556 no O12 O13 2.8351(11) 2_556 no O13 O13 3.1528(12) 2_556 no O13 C3 3.2592(13) 2_456 no O13 C2 3.1752(13) 2_556 no O14 C23 3.2380(15) . no loop_ _geom_hbond_atom_site_label_D _geom_hbond_atom_site_label_H _geom_hbond_atom_site_label_A _geom_hbond_site_symmetry_A _geom_hbond_angle_DHA _geom_hbond_distance_DH _geom_hbond_distance_HA _geom_hbond_distance_DA _geom_hbond_publ_flag O12 H121 O22 2_556 166.8(17) 0.827(17) 2.094(17) 2.9062(16) yes O13 H131 O12 2_456 166.8(14) 0.886(16) 1.965(16) 2.8352(16) yes 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_publ_flag C15 O14 C4 C5 161.82(9) no C4 O14 C15 C16 176.83(9) no C4 O14 C15 O22 -4.28(16) no C15 O14 C4 C3 -100.01(10) no C8 C1 C2 O13 -178.29(8) no C11 C1 C2 C3 -171.99(8) no O12 C1 C8 C7 -50.49(11) no O12 C1 C2 C3 61.95(10) no C2 C1 C8 C7 68.10(11) no C2 C1 C8 C9 -165.52(9) no C11 C1 C8 C7 -168.56(8) no C11 C1 C8 C9 -42.18(10) no O12 C1 C11 C10 -87.45(10) no C2 C1 C11 C10 147.75(9) no O12 C1 C8 C9 75.89(10) no O12 C1 C2 O13 -60.09(10) no C11 C1 C2 O13 65.98(11) no C8 C1 C2 C3 -56.26(11) no C8 C1 C11 C10 28.45(10) no C1 C2 C3 C4 133.85(9) no C1 C2 C3 C6 32.96(12) no O13 C2 C3 C6 153.98(9) no O13 C2 C3 C4 -105.13(9) no C6 C3 C4 O14 -97.49(9) no C2 C3 C6 C7 -18.95(14) no C2 C3 C6 C23 -145.85(9) no C4 C3 C6 C5 -13.38(8) no C2 C3 C4 C5 -106.37(9) no C4 C3 C6 C23 99.40(9) no C6 C3 C4 C5 13.54(8) no C2 C3 C6 C5 101.38(10) no C4 C3 C6 C7 -133.71(10) no C2 C3 C4 O14 142.60(8) no O14 C4 C5 C6 99.67(9) no C3 C4 C5 C6 -13.76(8) no C4 C5 C6 C3 13.51(8) no C4 C5 C6 C23 -98.36(9) no C4 C5 C6 C7 134.05(9) no C5 C6 C7 C8 -75.58(12) no C23 C6 C7 C8 155.60(9) no C3 C6 C7 C8 27.93(13) no C6 C7 C8 C1 -52.25(12) no C6 C7 C8 C9 -169.91(9) no C1 C8 C9 C10 40.17(11) no C7 C8 C9 C10 162.58(9) no C8 C9 C10 C24 95.75(10) no C8 C9 C10 C25 -142.71(9) no C8 C9 C10 C11 -22.30(11) no C25 C10 C11 C1 115.51(10) no C9 C10 C11 C1 -3.99(11) no C24 C10 C11 C1 -122.61(10) no O14 C15 C16 C17 -21.61(15) no O14 C15 C16 C21 159.42(10) no O22 C15 C16 C17 159.48(12) no O22 C15 C16 C21 -19.49(17) no C15 C16 C17 C18 -179.60(11) no C21 C16 C17 C18 -0.65(17) no C15 C16 C21 C20 -179.89(11) no C17 C16 C21 C20 1.13(18) no C16 C17 C18 C19 -0.38(18) no C17 C18 C19 C20 0.9(2) no C18 C19 C20 C21 -0.5(2) no C19 C20 C21 C16 -0.6(2) no