#------------------------------------------------------------------------------ #$Date: 2021-09-21 01:14:54 +0300 (Tue, 21 Sep 2021) $ #$Revision: 269219 $ #$URL: file:///home/coder/svn-repositories/cod/cif/1/56/46/1564697.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_1564697 loop_ _publ_author_name 'Haughey, Maxwell B.' 'Christensen, Kirsten E.' 'Poole, Darren L.' 'Donohoe, Timothy J.' _publ_section_title ; Development of an enolate alkynylation approach towards the synthesis of the taiwanschirin natural products ; _journal_name_full 'Chemical Science' _journal_paper_doi 10.1039/D1SC04247E _journal_year 2021 _chemical_absolute_configuration ad _chemical_formula_moiety 'C15 H16 O5' _chemical_formula_sum 'C15 H16 O5' _chemical_formula_weight 276.29 _chemical_melting_point ? _space_group_IT_number 29 _space_group_name_Hall 'P 2c -2ac' _space_group_name_H-M_alt 'P c a 21' _symmetry_cell_setting orthorhombic _symmetry_space_group_name_Hall 'P 2c -2ac' _symmetry_space_group_name_H-M 'P c a 21' _atom_sites_solution_hydrogens difmap _atom_sites_solution_primary other _audit_creation_date 2018-08-16 _audit_creation_method CRYSTALS_ver_14.61_build_6720 _audit_update_record ; 2021-03-23 deposited with the CCDC. 2021-09-15 downloaded from the CCDC. ; _cell_angle_alpha 90 _cell_angle_beta 90 _cell_angle_gamma 90 _cell_formula_units_Z 8 _cell_length_a 14.0413(3) _cell_length_b 7.0334(2) _cell_length_c 27.4163(9) _cell_measurement_reflns_used 5831 _cell_measurement_temperature 150 _cell_measurement_theta_max 76 _cell_measurement_theta_min 6 _cell_volume 2707.58(13) _computing_cell_refinement ; CrysAlisPro (Rigaku Oxford Diffraction, 2017) ; _computing_data_collection 'SuperNova, (Oxford Diffraction, 2010)' _computing_data_reduction ; CrysAlisPro (Rigaku Oxford Diffraction, 2017) ; _computing_molecular_graphics 'CAMERON (Watkin et al., 1996)' _computing_publication_material 'CRYSTALS (Betteridge et al., 2003)' _computing_structure_refinement 'CRYSTALS (Betteridge et al., 2003)' _computing_structure_solution 'Superflip (Palatinus & Chapuis, 2007)' _diffrn_ambient_temperature 150 _diffrn_measured_fraction_theta_full 0.996 _diffrn_measured_fraction_theta_max 0.996 _diffrn_measurement_device Area _diffrn_measurement_device_type 'Oxford Diffraction SuperNova' _diffrn_measurement_method \w _diffrn_radiation_monochromator 'focussing mirrors' _diffrn_radiation_type 'Cu K\a' _diffrn_radiation_wavelength 1.54184 _diffrn_reflns_av_R_equivalents 0.027 _diffrn_reflns_av_sigmaI/netI 0.0409 _diffrn_reflns_limit_h_max 17 _diffrn_reflns_limit_h_min -10 _diffrn_reflns_limit_k_max 8 _diffrn_reflns_limit_k_min -8 _diffrn_reflns_limit_l_max 33 _diffrn_reflns_limit_l_min -34 _diffrn_reflns_number 13755 _diffrn_reflns_theta_full 76.653 _diffrn_reflns_theta_max 76.653 _diffrn_reflns_theta_min 3.224 _diffrn_standards_number 0 _exptl_absorpt_coefficient_mu 0.851 _exptl_absorpt_correction_T_max 0.97 _exptl_absorpt_correction_T_min 0.72 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details ; CrysAlisPro (Rigaku Oxford Diffraction, 2017) ; _exptl_crystal_colour clear_pale_colourless _exptl_crystal_density_diffrn 1.355 _exptl_crystal_density_meas ? _exptl_crystal_density_method 'not measured' _exptl_crystal_description lath _exptl_crystal_F_000 1167.994 _exptl_crystal_size_max 0.21 _exptl_crystal_size_mid 0.18 _exptl_crystal_size_min 0.03 _refine_diff_density_max 0.25 _refine_diff_density_min -0.18 _refine_ls_abs_structure_details ; Parsons, Flack & Wagner (2013), 2288 Friedel Pairs ; _refine_ls_abs_structure_Flack -0.05(9) _refine_ls_extinction_method None _refine_ls_goodness_of_fit_ref 0.9983 _refine_ls_hydrogen_treatment constr _refine_ls_matrix_type full _refine_ls_number_parameters 362 _refine_ls_number_reflns 5386 _refine_ls_number_restraints 1 _refine_ls_R_factor_all 0.0391 _refine_ls_R_factor_gt 0.0355 _refine_ls_shift/su_max 0.0004106 _refine_ls_shift/su_mean 0.0000546 _refine_ls_structure_factor_coef Fsqd _refine_ls_weighting_details ; Method= Modified Sheldrick w=1/[\s^2^(F^2^) + ( 0.05P)^2^ + 0.62P] ,where P=(max(Fo^2^,0) + 2Fc^2^)/3 ; _refine_ls_weighting_scheme calc _refine_ls_wR_factor_all 0.0950 _refine_ls_wR_factor_gt 0.0906 _refine_ls_wR_factor_ref 0.0949 _reflns_limit_h_max 17 _reflns_limit_h_min 0 _reflns_limit_k_max 8 _reflns_limit_k_min 0 _reflns_limit_l_max 33 _reflns_limit_l_min -34 _reflns_number_gt 4983 _reflns_number_total 5388 _reflns_threshold_expression I>2.0\s(I) _oxford_diffrn_Wilson_B_factor 2.66 _oxford_diffrn_Wilson_scale 0.04 _oxford_refine_ls_r_factor_ref 0.0390 _oxford_refine_ls_scale 5.25(7) _oxford_reflns_number_all 5387 _oxford_structure_analysis_title 7002 _iucr_refine_instructions_details ; # # Punched on 16/08/18 at 14:43:11 # #LIST 12 BLOCK SCALE X'S U'S CONT ENANTIO RIDE C ( 1,X'S) H ( 12,X'S) H ( 11,X'S) RIDE C ( 4,X'S) H ( 41,X'S) RIDE C ( 5,X'S) H ( 51,X'S) RIDE C ( 6,X'S) H ( 61,X'S) RIDE C ( 7,X'S) H ( 71,X'S) RIDE C ( 14,X'S) H ( 141,X'S) H ( 142,X'S) H ( 143,X'S) RIDE C ( 15,X'S) H ( 152,X'S) H ( 153,X'S) H ( 151,X'S) RIDE C ( 21,X'S) H ( 211,X'S) RIDE C ( 25,X'S) H ( 252,X'S) H ( 253,X'S) H ( 251,X'S) RIDE C ( 51,X'S) H ( 512,X'S) H ( 511,X'S) RIDE C ( 54,X'S) H ( 541,X'S) RIDE C ( 55,X'S) H ( 551,X'S) RIDE C ( 56,X'S) H ( 561,X'S) RIDE C ( 57,X'S) H ( 571,X'S) RIDE C ( 64,X'S) H ( 641,X'S) H ( 642,X'S) H ( 643,X'S) RIDE C ( 65,X'S) H ( 652,X'S) H ( 653,X'S) H ( 651,X'S) RIDE C ( 71,X'S) H ( 711,X'S) RIDE C ( 75,X'S) H ( 752,X'S) H ( 753,X'S) H ( 751,X'S) END # # Punched on 16/08/18 at 14:43:11 # #LIST 16 NO REM HREST START (DO NOT REMOVE THIS LINE) REM HREST END (DO NOT REMOVE THIS LINE) END ; _cod_data_source_file d1sc04247e2.cif _cod_data_source_block 7002 _cod_depositor_comments ; The following automatic conversions were performed: data item '_chemical_melting_point' value 'not measured' was changed to '?' -- the value is undefined or not given. data item '_exptl_crystal_density_meas' value 'not measured' was changed to '?' -- the value is perceived as not measured. Automatic conversion script Id: cif_fix_values 7556 2019-12-06 15:28:31Z antanas ; _cod_original_sg_symbol_H-M 'P c a 21 ' _cod_database_code 1564697 _oxford_refine_reflns_threshold_expression_ref I>-3.0\s(I) _oxford_hooft_y -0.07(9) _oxford_bijvoet_difference -0.05(9) _oxford_refined_flack_x -0.03(15) loop_ _symmetry_equiv_pos_as_xyz x,y,z -x,-y,z+1/2 -x+1/2,y,z+1/2 x+1/2,-y,z 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 _atom_site_refinement_flags_posn _atom_site_refinement_flags_adp _atom_site_refinement_flags_occupancy _atom_site_disorder_assembly _atom_site_disorder_group _atom_site_attached_hydrogens C1 C 0.59456(15) 0.3292(3) 0.49998(9) 0.0334 1.0000 Uani . . . . . . O2 O 0.67776(10) 0.3733(2) 0.52930(7) 0.0347 1.0000 Uani . . . . . . C3 C 0.70288(14) 0.5560(3) 0.51893(8) 0.0305 1.0000 Uani . . . . . . C4 C 0.77549(15) 0.6552(3) 0.54253(9) 0.0369 1.0000 Uani . . . . . . C5 C 0.79433(15) 0.8380(3) 0.52661(9) 0.0401 1.0000 Uani . . . . . . C6 C 0.74370(15) 0.9202(3) 0.48862(9) 0.0369 1.0000 Uani . . . . . . C7 C 0.67175(14) 0.8191(3) 0.46509(9) 0.0308 1.0000 Uani . . . . . . C8 C 0.65090(13) 0.6368(3) 0.48123(8) 0.0258 1.0000 Uani . . . . . . C9 C 0.58439(12) 0.4843(3) 0.46052(8) 0.0249 1.0000 Uani . . . . . . C10 C 0.47964(13) 0.5401(3) 0.45519(8) 0.0272 1.0000 Uani . . . . . . C11 C 0.63535(12) 0.4275(3) 0.41331(8) 0.0272 1.0000 Uani . . . . . . O12 O 0.70069(10) 0.3174(2) 0.41211(7) 0.0395 1.0000 Uani . . . . . . O13 O 0.60633(10) 0.5331(2) 0.37550(6) 0.0338 1.0000 Uani . . . . . . C14 C 0.66566(19) 0.5196(4) 0.33235(10) 0.0495 1.0000 Uani . . . . . . C15 C 0.44799(16) 0.7148(3) 0.48223(10) 0.0422 1.0000 Uani . . . . . . C21 C 0.41432(13) 0.4361(3) 0.43161(8) 0.0303 1.0000 Uani . . . . . . C22 C 0.43103(13) 0.2520(3) 0.40757(8) 0.0293 1.0000 Uani . . . . . . O23 O 0.50236(10) 0.1571(2) 0.40983(7) 0.0369 1.0000 Uani . . . . . . O24 O 0.35334(10) 0.1990(2) 0.38235(7) 0.0410 1.0000 Uani . . . . . . C25 C 0.35609(17) 0.0124(4) 0.36037(11) 0.0508 1.0000 Uani . . . . . . C51 C 0.81883(14) 0.1771(3) 0.64585(8) 0.0284 1.0000 Uani . . . . . . O52 O 0.90652(10) 0.13755(19) 0.61958(6) 0.0307 1.0000 Uani . . . . . . C53 C 0.93225(13) -0.0444(3) 0.63109(8) 0.0262 1.0000 Uani . . . . . . C54 C 1.00797(14) -0.1388(3) 0.60973(8) 0.0317 1.0000 Uani . . . . . . C55 C 1.02667(14) -0.3231(3) 0.62579(9) 0.0341 1.0000 Uani . . . . . . C56 C 0.97210(14) -0.4076(3) 0.66196(9) 0.0323 1.0000 Uani . . . . . . C57 C 0.89742(13) -0.3080(3) 0.68394(8) 0.0286 1.0000 Uani . . . . . . C58 C 0.87732(12) -0.1255(3) 0.66754(8) 0.0244 1.0000 Uani . . . . . . C59 C 0.80930(12) 0.0271(2) 0.68711(8) 0.0237 1.0000 Uani . . . . . . C60 C 0.70514(13) -0.0315(3) 0.69380(8) 0.0268 1.0000 Uani . . . . . . C61 C 0.86094(12) 0.0912(3) 0.73328(8) 0.0267 1.0000 Uani . . . . . . O62 O 0.92530(10) 0.2040(2) 0.73334(7) 0.0356 1.0000 Uani . . . . . . O63 O 0.83448(10) -0.0106(2) 0.77209(6) 0.0326 1.0000 Uani . . . . . . C64 C 0.89564(17) 0.0083(4) 0.81464(10) 0.0446 1.0000 Uani . . . . . . C65 C 0.67307(14) -0.2083(3) 0.66752(10) 0.0364 1.0000 Uani . . . . . . C71 C 0.64069(13) 0.0712(3) 0.71811(8) 0.0288 1.0000 Uani . . . . . . C72 C 0.65698(13) 0.2551(3) 0.74193(8) 0.0293 1.0000 Uani . . . . . . O73 O 0.72628(10) 0.3552(2) 0.73751(7) 0.0359 1.0000 Uani . . . . . . O74 O 0.58180(10) 0.3030(2) 0.76963(7) 0.0400 1.0000 Uani . . . . . . C75 C 0.58424(17) 0.4906(4) 0.79152(11) 0.0531 1.0000 Uani . . . . . . H12 H 0.5398 0.3328 0.5220 0.0407 1.0000 Uiso R . . . . . H11 H 0.6042 0.2068 0.4844 0.0389 1.0000 Uiso R . . . . . H41 H 0.8099 0.5993 0.5677 0.0438 1.0000 Uiso R . . . . . H51 H 0.8422 0.9079 0.5416 0.0486 1.0000 Uiso R . . . . . H61 H 0.7561 1.0481 0.4785 0.0434 1.0000 Uiso R . . . . . H71 H 0.6361 0.8753 0.4387 0.0367 1.0000 Uiso R . . . . . H152 H 0.3800 0.7228 0.4807 0.0629 1.0000 Uiso R . . . . . H153 H 0.4694 0.7109 0.5168 0.0626 1.0000 Uiso R . . . . . H151 H 0.4742 0.8272 0.4674 0.0621 1.0000 Uiso R . . . . . H211 H 0.3522 0.4830 0.4304 0.0371 1.0000 Uiso R . . . . . H252 H 0.3163 0.0217 0.3309 0.0764 1.0000 Uiso R . . . . . H253 H 0.3291 -0.0800 0.3842 0.0772 1.0000 Uiso R . . . . . H251 H 0.4195 -0.0230 0.3526 0.0766 1.0000 Uiso R . . . . . H512 H 0.8212 0.3054 0.6578 0.0338 1.0000 Uiso R . . . . . H511 H 0.7657 0.1633 0.6231 0.0335 1.0000 Uiso R . . . . . H541 H 1.0447 -0.0788 0.5863 0.0379 1.0000 Uiso R . . . . . H551 H 1.0772 -0.3904 0.6127 0.0415 1.0000 Uiso R . . . . . H561 H 0.9871 -0.5356 0.6725 0.0383 1.0000 Uiso R . . . . . H571 H 0.8612 -0.3643 0.7099 0.0345 1.0000 Uiso R . . . . . H652 H 0.6047 -0.2189 0.6687 0.0540 1.0000 Uiso R . . . . . H653 H 0.7019 -0.3193 0.6830 0.0542 1.0000 Uiso R . . . . . H651 H 0.6962 -0.2052 0.6335 0.0544 1.0000 Uiso R . . . . . H711 H 0.5776 0.0269 0.7202 0.0350 1.0000 Uiso R . . . . . H752 H 0.5257 0.5522 0.7863 0.0807 1.0000 Uiso R . . . . . H753 H 0.5960 0.4685 0.8245 0.0802 1.0000 Uiso R . . . . . H751 H 0.6357 0.5646 0.7776 0.0800 1.0000 Uiso R . . . . . H141 H 0.6350 0.5999 0.3086 0.0739 1.0000 Uiso R . . . . . H142 H 0.7279 0.5710 0.3407 0.0745 1.0000 Uiso R . . . . . H143 H 0.6688 0.3911 0.3202 0.0741 1.0000 Uiso R . . . . . H641 H 0.8610 -0.0438 0.8425 0.0664 1.0000 Uiso R . . . . . H642 H 0.9160 0.1414 0.8205 0.0672 1.0000 Uiso R . . . . . H643 H 0.9509 -0.0717 0.8094 0.0678 1.0000 Uiso 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 0.0288(9) 0.0328(10) 0.0385(11) 0.0080(8) -0.0040(8) 0.0010(8) O2 0.0312(7) 0.0384(8) 0.0344(8) 0.0072(6) -0.0056(6) 0.0032(6) C3 0.0268(9) 0.0363(10) 0.0283(10) -0.0026(8) 0.0005(7) 0.0058(8) C4 0.0324(10) 0.0495(12) 0.0287(10) -0.0064(9) -0.0080(8) 0.0042(9) C5 0.0319(10) 0.0469(12) 0.0415(12) -0.0146(10) -0.0052(9) -0.0043(9) C6 0.0324(10) 0.0328(9) 0.0455(12) -0.0063(10) -0.0006(9) -0.0040(8) C7 0.0282(9) 0.0291(9) 0.0352(11) -0.0016(8) -0.0010(8) 0.0010(7) C8 0.0228(8) 0.0285(9) 0.0261(9) -0.0026(7) 0.0002(7) 0.0022(7) C9 0.0218(8) 0.0243(8) 0.0286(10) 0.0006(7) 0.0005(6) 0.0023(7) C10 0.0226(9) 0.0292(9) 0.0299(10) 0.0033(8) 0.0032(7) 0.0039(7) C11 0.0176(8) 0.0310(9) 0.0329(10) -0.0052(8) 0.0006(7) -0.0039(6) O12 0.0231(6) 0.0439(8) 0.0515(10) -0.0160(7) 0.0038(6) 0.0029(6) O13 0.0317(7) 0.0441(8) 0.0255(7) -0.0005(6) 0.0042(5) -0.0069(6) C14 0.0525(13) 0.0630(16) 0.0329(12) -0.0074(11) 0.0163(10) -0.0200(13) C15 0.0279(10) 0.0378(11) 0.0609(15) -0.0085(10) 0.0058(10) 0.0081(8) C21 0.0178(8) 0.0357(10) 0.0373(11) 0.0053(8) 0.0020(7) 0.0021(7) C22 0.0212(8) 0.0367(10) 0.0299(9) 0.0030(8) 0.0023(7) -0.0060(7) O23 0.0263(6) 0.0358(7) 0.0488(9) -0.0086(7) -0.0036(6) -0.0002(6) O24 0.0253(7) 0.0538(9) 0.0439(9) -0.0063(8) -0.0036(6) -0.0044(7) C25 0.0334(11) 0.0592(15) 0.0600(17) -0.0177(13) -0.0050(11) -0.0132(11) C51 0.0252(9) 0.0270(9) 0.0330(10) 0.0004(8) 0.0013(7) 0.0004(7) O52 0.0299(7) 0.0286(7) 0.0335(8) 0.0028(6) 0.0060(6) -0.0004(5) C53 0.0254(8) 0.0261(8) 0.0271(9) -0.0032(7) -0.0032(7) -0.0018(7) C54 0.0259(9) 0.0388(10) 0.0305(10) -0.0058(8) 0.0028(8) -0.0032(7) C55 0.0275(9) 0.0384(10) 0.0363(11) -0.0103(9) 0.0009(8) 0.0064(8) C56 0.0302(9) 0.0279(9) 0.0388(11) -0.0029(8) -0.0031(8) 0.0054(8) C57 0.0263(9) 0.0274(9) 0.0320(10) -0.0024(8) -0.0009(7) 0.0003(7) C58 0.0187(7) 0.0270(9) 0.0275(9) -0.0050(7) -0.0009(7) -0.0011(7) C59 0.0210(8) 0.0219(8) 0.0283(10) -0.0023(7) 0.0002(7) 0.0005(7) C60 0.0214(8) 0.0256(8) 0.0333(10) 0.0021(8) -0.0025(7) -0.0016(7) C61 0.0195(8) 0.0299(8) 0.0306(9) -0.0044(8) 0.0013(7) 0.0038(6) O62 0.0241(6) 0.0380(7) 0.0447(8) -0.0107(7) -0.0007(6) -0.0050(5) O63 0.0289(6) 0.0409(8) 0.0280(7) -0.0017(6) -0.0029(5) 0.0035(6) C64 0.0426(11) 0.0586(15) 0.0327(12) -0.0044(10) -0.0116(9) 0.0143(11) C65 0.0248(9) 0.0323(10) 0.0520(13) -0.0082(9) -0.0014(9) -0.0051(8) C71 0.0183(8) 0.0335(9) 0.0348(10) 0.0022(8) -0.0011(7) -0.0013(7) C72 0.0201(8) 0.0370(10) 0.0308(10) -0.0006(8) -0.0029(7) 0.0053(7) O73 0.0283(7) 0.0317(7) 0.0476(9) -0.0083(7) 0.0046(6) -0.0016(5) O74 0.0254(7) 0.0522(9) 0.0423(9) -0.0123(8) 0.0045(6) 0.0025(6) C75 0.0347(11) 0.0658(16) 0.0589(17) -0.0265(13) 0.0073(10) 0.0068(12) 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_site_symmetry_1 _geom_angle_atom_site_label_2 _geom_angle_site_symmetry_2 _geom_angle_atom_site_label_3 _geom_angle_site_symmetry_3 _geom_angle _geom_angle_publ_flag O2 . C1 . C9 . 108.15(16) yes O2 . C1 . H12 . 106.6 no C9 . C1 . H12 . 110.0 no O2 . C1 . H11 . 108.7 no C9 . C1 . H11 . 109.4 no H12 . C1 . H11 . 113.8 no C1 . O2 . C3 . 107.12(16) yes O2 . C3 . C4 . 124.34(19) yes O2 . C3 . C8 . 113.92(18) yes C4 . C3 . C8 . 121.7(2) yes C3 . C4 . C5 . 117.3(2) yes C3 . C4 . H41 . 120.8 no C5 . C4 . H41 . 121.9 no C4 . C5 . C6 . 121.8(2) yes C4 . C5 . H51 . 119.5 no C6 . C5 . H51 . 118.8 no C5 . C6 . C7 . 120.4(2) yes C5 . C6 . H61 . 121.0 no C7 . C6 . H61 . 118.6 no C6 . C7 . C8 . 118.5(2) yes C6 . C7 . H71 . 121.0 no C8 . C7 . H71 . 120.5 no C7 . C8 . C3 . 120.33(18) yes C7 . C8 . C9 . 131.12(18) yes C3 . C8 . C9 . 108.09(17) yes C1 . C9 . C8 . 100.30(15) yes C1 . C9 . C10 . 109.71(15) yes C8 . C9 . C10 . 116.26(15) yes C1 . C9 . C11 . 111.40(16) yes C8 . C9 . C11 . 102.17(14) yes C10 . C9 . C11 . 115.82(16) yes C9 . C10 . C15 . 116.57(17) yes C9 . C10 . C21 . 124.38(17) yes C15 . C10 . C21 . 118.83(18) yes C9 . C11 . O12 . 123.23(19) yes C9 . C11 . O13 . 111.57(15) yes O12 . C11 . O13 . 124.67(19) yes C11 . O13 . C14 . 114.89(18) yes O13 . C14 . H141 . 104.8 no O13 . C14 . H142 . 107.4 no H141 . C14 . H142 . 110.0 no O13 . C14 . H143 . 111.7 no H141 . C14 . H143 . 109.6 no H142 . C14 . H143 . 112.8 no C10 . C15 . H152 . 108.8 no C10 . C15 . H153 . 111.0 no H152 . C15 . H153 . 110.1 no C10 . C15 . H151 . 110.5 no H152 . C15 . H151 . 108.4 no H153 . C15 . H151 . 108.0 no C10 . C21 . C22 . 125.97(17) yes C10 . C21 . H211 . 117.6 no C22 . C21 . H211 . 116.4 no C21 . C22 . O23 . 126.63(18) yes C21 . C22 . O24 . 110.17(17) yes O23 . C22 . O24 . 123.19(19) yes C22 . O24 . C25 . 116.40(18) yes O24 . C25 . H252 . 105.5 no O24 . C25 . H253 . 108.0 no H252 . C25 . H253 . 111.5 no O24 . C25 . H251 . 110.9 no H252 . C25 . H251 . 111.5 no H253 . C25 . H251 . 109.4 no O52 . C51 . C59 . 107.68(15) yes O52 . C51 . H512 . 108.7 no C59 . C51 . H512 . 113.1 no O52 . C51 . H511 . 108.2 no C59 . C51 . H511 . 109.3 no H512 . C51 . H511 . 109.8 no C51 . O52 . C53 . 106.79(15) yes O52 . C53 . C54 . 123.68(19) yes O52 . C53 . C58 . 113.89(17) yes C54 . C53 . C58 . 122.40(18) yes C53 . C54 . C55 . 117.21(19) yes C53 . C54 . H541 . 120.2 no C55 . C54 . H541 . 122.5 no C54 . C55 . C56 . 121.37(19) yes C54 . C55 . H551 . 119.9 no C56 . C55 . H551 . 118.8 no C55 . C56 . C57 . 120.49(19) yes C55 . C56 . H561 . 119.5 no C57 . C56 . H561 . 120.0 no C56 . C57 . C58 . 118.44(19) yes C56 . C57 . H571 . 120.6 no C58 . C57 . H571 . 120.9 no C57 . C58 . C53 . 120.06(17) yes C57 . C58 . C59 . 131.30(18) yes C53 . C58 . C59 . 108.11(16) yes C58 . C59 . C51 . 99.63(15) yes C58 . C59 . C60 . 116.65(14) yes C51 . C59 . C60 . 110.65(15) yes C58 . C59 . C61 . 101.59(14) yes C51 . C59 . C61 . 111.24(15) yes C60 . C59 . C61 . 115.72(16) yes C59 . C60 . C65 . 116.79(16) yes C59 . C60 . C71 . 124.15(17) yes C65 . C60 . C71 . 118.86(17) yes C59 . C61 . O62 . 123.56(18) yes C59 . C61 . O63 . 111.73(15) yes O62 . C61 . O63 . 124.18(18) yes C61 . O63 . C64 . 115.20(17) yes O63 . C64 . H641 . 107.4 no O63 . C64 . H642 . 112.7 no H641 . C64 . H642 . 111.7 no O63 . C64 . H643 . 107.6 no H641 . C64 . H643 . 107.2 no H642 . C64 . H643 . 110.0 no C60 . C65 . H652 . 110.2 no C60 . C65 . H653 . 109.1 no H652 . C65 . H653 . 109.7 no C60 . C65 . H651 . 109.6 no H652 . C65 . H651 . 111.2 no H653 . C65 . H651 . 107.0 no C60 . C71 . C72 . 126.39(17) yes C60 . C71 . H711 . 119.2 no C72 . C71 . H711 . 114.4 no C71 . C72 . O73 . 126.53(18) yes C71 . C72 . O74 . 110.50(16) yes O73 . C72 . O74 . 122.96(19) yes C72 . O74 . C75 . 116.34(17) yes O74 . C75 . H752 . 109.6 no O74 . C75 . H753 . 104.7 no H752 . C75 . H753 . 112.3 no O74 . C75 . H751 . 110.1 no H752 . C75 . H751 . 110.1 no H753 . C75 . H751 . 109.8 no loop_ _geom_bond_atom_site_label_1 _geom_bond_site_symmetry_1 _geom_bond_atom_site_label_2 _geom_bond_site_symmetry_2 _geom_bond_distance _geom_bond_publ_flag C1 . O2 . 1.452(2) yes C1 . C9 . 1.543(3) yes C1 . H12 . 0.977 no C1 . H11 . 0.970 no O2 . C3 . 1.363(3) yes C3 . C4 . 1.395(3) yes C3 . C8 . 1.387(3) yes C4 . C5 . 1.383(3) yes C4 . H41 . 0.930 no C5 . C6 . 1.387(3) yes C5 . H51 . 0.928 no C6 . C7 . 1.394(3) yes C6 . H61 . 0.957 no C7 . C8 . 1.388(3) yes C7 . H71 . 0.964 no C8 . C9 . 1.531(3) yes C9 . C10 . 1.529(2) yes C9 . C11 . 1.532(3) yes C10 . C15 . 1.502(3) yes C10 . C21 . 1.339(3) yes C11 . O12 . 1.201(2) yes C11 . O13 . 1.338(3) yes O13 . C14 . 1.450(2) yes C14 . H141 . 0.963 no C14 . H142 . 0.973 no C14 . H143 . 0.965 no C15 . H152 . 0.958 no C15 . H153 . 0.995 no C15 . H151 . 0.962 no C21 . C22 . 1.472(3) yes C21 . H211 . 0.933 no C22 . O23 . 1.205(2) yes C22 . O24 . 1.344(2) yes O24 . C25 . 1.445(3) yes C25 . H252 . 0.984 no C25 . H253 . 0.996 no C25 . H251 . 0.948 no C51 . O52 . 1.453(2) yes C51 . C59 . 1.553(3) yes C51 . H512 . 0.961 no C51 . H511 . 0.977 no O52 . C53 . 1.367(2) yes C53 . C54 . 1.383(3) yes C53 . C58 . 1.385(3) yes C54 . C55 . 1.394(3) yes C54 . H541 . 0.926 no C55 . C56 . 1.387(3) yes C55 . H551 . 0.925 no C56 . C57 . 1.398(3) yes C56 . H561 . 0.968 no C57 . C58 . 1.389(3) yes C57 . H571 . 0.960 no C58 . C59 . 1.534(2) yes C59 . C60 . 1.531(2) yes C59 . C61 . 1.527(3) yes C60 . C65 . 1.506(3) yes C60 . C71 . 1.336(3) yes C61 . O62 . 1.202(2) yes C61 . O63 . 1.335(3) yes O63 . C64 . 1.455(2) yes C64 . H641 . 0.978 no C64 . H642 . 0.992 no C64 . H643 . 0.969 no C65 . H652 . 0.963 no C65 . H653 . 0.977 no C65 . H651 . 0.987 no C71 . C72 . 1.467(3) yes C71 . H711 . 0.941 no C72 . O73 . 1.207(2) yes C72 . O74 . 1.343(2) yes O74 . C75 . 1.450(3) yes C75 . H752 . 0.940 no C75 . H753 . 0.933 no C75 . H751 . 0.968 no loop_ _geom_hbond_atom_site_label_D _geom_hbond_site_symmetry_D _geom_hbond_atom_site_label_H _geom_hbond_site_symmetry_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 C21 . H211 . O12 4_465 164 0.93 2.60 3.506(3) yes C25 . H253 . O12 4_455 152 1.00 2.57 3.486(3) yes loop_ _oxford_refln_omitted_index_h _oxford_refln_omitted_index_k _oxford_refln_omitted_index_l _oxford_refln_omitted_flag _oxford_refln_omitted_details 5 2 31 x .