#\#CIF1.1 ########################################################################## # Crystallographic Information Format file # Produced by PyCifRW module # # This is a CIF file. CIF has been adopted by the International # Union of Crystallography as the standard for data archiving and # transmission. # # For information on this file format, follow the CIF links at # http://www.iucr.org ########################################################################## data_marc _atom_sites_solution_hydrogens geom _atom_sites_solution_primary ? _atom_sites_solution_secondary ? _audit_creation_method SHELXL-2013 _cell_angle_alpha 90 _cell_angle_beta 101.424(4) _cell_angle_gamma 90 _cell_formula_units_Z 8 _cell_length_a 24.445(7) _cell_length_b 7.241(2) _cell_length_c 17.657(5) _cell_measurement_reflns_used 2803 _cell_measurement_temperature 200(2) _cell_measurement_theta_max 27.58 _cell_measurement_theta_min 2.35 _cell_volume 3063.3(16) _chemical_formula_moiety ? _chemical_formula_sum 'C17 H20 O4' _chemical_formula_weight 288.33 _chemical_melting_point ? _chemical_name_common ? _chemical_name_systematic '? ' _computing_cell_refinement 'Bruker SAINT' _computing_data_collection 'Bruker APEX2' _computing_data_reduction 'Bruker SAINT' _computing_molecular_graphics 'Bruker SHELXTL' _computing_publication_material 'Bruker SHELXTL' _computing_structure_refinement 'SHELXL-2013 (Sheldrick, 2013)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 2008)' _diffrn_ambient_temperature 200(2) _diffrn_detector_area_resol_mean 8.33 _diffrn_measured_fraction_theta_full 0.993 _diffrn_measured_fraction_theta_max 0.986 _diffrn_measurement_device_type 'Bruker APEX-II CCD' _diffrn_measurement_method '\f and \w scans' _diffrn_radiation_type MoK\a _diffrn_radiation_wavelength 0.71073 _diffrn_reflns_Laue_measured_fraction_full 0.993 _diffrn_reflns_Laue_measured_fraction_max 0.986 _diffrn_reflns_av_R_equivalents 0.0254 _diffrn_reflns_av_unetI/netI 0.0296 _diffrn_reflns_limit_h_max 31 _diffrn_reflns_limit_h_min -29 _diffrn_reflns_limit_k_max 9 _diffrn_reflns_limit_k_min -9 _diffrn_reflns_limit_l_max 23 _diffrn_reflns_limit_l_min -22 _diffrn_reflns_number 9710 _diffrn_reflns_point_group_measured_fraction_full 0.993 _diffrn_reflns_point_group_measured_fraction_max 0.986 _diffrn_reflns_theta_full 25.000 _diffrn_reflns_theta_max 27.650 _diffrn_reflns_theta_min 2.354 _diffrn_source ? _exptl_absorpt_coefficient_mu 0.088 _exptl_absorpt_correction_T_max 0.7456 _exptl_absorpt_correction_T_min 0.6892 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details 'APEX2 (Bruker, 2007)' _exptl_crystal_F_000 1232 _exptl_crystal_colour colourless _exptl_crystal_density_diffrn 1.250 _exptl_crystal_density_meas ? _exptl_crystal_density_method ? _exptl_crystal_description block _exptl_crystal_size_max 0.600 _exptl_crystal_size_mid 0.557 _exptl_crystal_size_min 0.440 _exptl_special_details ; Data collection is performed with four batch runs at \f = 0.00 \% (600 frames), at \f = 90.00 \% (600 frames), at \f = 180 \% (600 frames) and at \f = 270 \% (600 frames). Frame width = 0.30 \& in \w. Data is merged, corrected for decay, and treated with multi-scan absorption corrections. ; _exptl_transmission_factor_max ? _exptl_transmission_factor_min ? _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. ; _refine_diff_density_max 0.343 _refine_diff_density_min -0.276 _refine_diff_density_rms 0.046 _refine_ls_R_factor_all 0.0551 _refine_ls_R_factor_gt 0.0451 _refine_ls_extinction_coef . _refine_ls_extinction_method none _refine_ls_goodness_of_fit_ref 1.039 _refine_ls_hydrogen_treatment constr _refine_ls_matrix_type full _refine_ls_number_parameters 194 _refine_ls_number_reflns 3528 _refine_ls_number_restraints 0 _refine_ls_restrained_S_all 1.039 _refine_ls_shift/su_max 0.005 _refine_ls_shift/su_mean 0.000 _refine_ls_structure_factor_coef Fsqd _refine_ls_wR_factor_gt 0.1208 _refine_ls_wR_factor_ref 0.1283 _refine_ls_weighting_details ; w=1/[\s^2^(Fo^2^)+(0.0706P)^2^+1.5021P] where P=(Fo^2^+2Fc^2^)/3 ; _refine_ls_weighting_scheme calc _refine_special_details '? ' _reflns_Friedel_coverage 0.000 _reflns_Friedel_fraction_full . _reflns_Friedel_fraction_max . _reflns_number_gt 2872 _reflns_number_total 3528 _reflns_special_details ; Reflections were merged by SHELXL according to the crystal class for the calculation of statistics and refinement. _reflns_Friedel_fraction is defined as the number of unique Friedel pairs measured divided by the number that would be possible theoretically, ignoring centric projections and systematic absences. ; _reflns_threshold_expression 'I > 2\s(I)' _shelx_estimated_absorpt_T_max 0.962 _shelx_estimated_absorpt_T_min 0.949 _shelx_res_checksum 90873 _shelx_res_file ; TITL marc in C2/c CELL 0.71073 24.4446 7.2407 17.6572 90.000 101.424 90.000 ZERR 8.00 0.0074 0.0023 0.0054 0.000 0.004 0.000 LATT 7 SYMM -x, y, -z+1/2 SFAC C H O UNIT 136 160 32 L.S. 10 ACTA 50 BOND $H FMAP 2 PLAN -4 OMIT 2 0 0 OMIT -9 1 2 SIZE 0.440 0.557 0.600 HTAB EQIV $1 -x, -y+1, -z+2 HTAB O4 O3_$1 CONF TEMP -73.000 WGHT 0.070600 1.502100 FVAR 0.15655 O1 3 0.203089 0.558741 0.915318 11.00000 0.02235 0.03864 = 0.05117 -0.00473 0.00917 0.00576 O2 3 0.114873 0.556561 0.848076 11.00000 0.02553 0.02765 = 0.02465 -0.00341 0.00772 0.00038 O3 3 0.064890 0.515418 1.000765 11.00000 0.02650 0.02898 = 0.04486 0.01267 0.01436 -0.00133 O4 3 -0.022554 0.770459 0.927592 11.00000 0.01754 0.03401 = 0.03783 0.00959 0.00684 -0.00056 AFIX 83 H4A 2 -0.028337 0.676840 0.952983 11.00000 -1.50000 AFIX 0 C1 1 0.121210 0.934103 0.931371 11.00000 0.02148 0.02038 = 0.01946 0.00113 0.00571 -0.00133 C2 1 0.132227 0.729225 0.964655 11.00000 0.01717 0.02252 = 0.02002 0.00321 0.00461 -0.00111 C3 1 0.074098 0.659723 0.969449 11.00000 0.02053 0.02373 = 0.02026 -0.00037 0.00709 -0.00206 C4 1 0.033139 0.794577 0.933804 11.00000 0.01757 0.02661 = 0.02032 0.00011 0.00570 0.00056 C5 1 0.057749 0.944529 0.910779 11.00000 0.02210 0.02494 = 0.01971 0.00009 0.00708 0.00217 C6 1 0.119392 0.935609 0.785931 11.00000 0.03508 0.02753 = 0.02633 0.00281 0.01005 0.00028 AFIX 43 H6A 2 0.081375 0.898717 0.777647 11.00000 -1.20000 AFIX 0 C7 1 0.144985 0.957305 0.722848 11.00000 0.05394 0.04096 = 0.02535 0.00687 0.01459 0.00853 AFIX 43 H7A 2 0.124502 0.934633 0.672113 11.00000 -1.20000 AFIX 0 C8 1 0.200154 1.011778 0.733826 11.00000 0.04968 0.05320 = 0.03897 0.02062 0.02939 0.01730 AFIX 43 H8A 2 0.217724 1.027238 0.690831 11.00000 -1.20000 AFIX 0 C9 1 0.229539 1.043564 0.807954 11.00000 0.02972 0.05722 = 0.04656 0.02155 0.01957 0.00883 AFIX 43 H9A 2 0.267543 1.080444 0.815822 11.00000 -1.20000 AFIX 0 C10 1 0.204019 1.022092 0.871159 11.00000 0.02471 0.03805 = 0.03418 0.01203 0.01035 0.00379 AFIX 43 H10 2 0.224704 1.045272 0.921736 11.00000 -1.20000 AFIX 0 C11 1 0.148402 0.966909 0.861070 11.00000 0.02551 0.01993 = 0.02468 0.00492 0.01070 0.00289 C12 1 0.141005 1.081702 0.993728 11.00000 0.03428 0.02827 = 0.02988 -0.00699 0.00903 -0.00587 AFIX 137 H12A 2 0.134459 1.204938 0.970775 11.00000 -1.50000 H12B 2 0.180953 1.065475 1.014558 11.00000 -1.50000 H12C 2 0.120184 1.068503 1.035483 11.00000 -1.50000 AFIX 0 C13 1 0.155110 0.605495 0.907704 11.00000 0.02092 0.01897 = 0.02779 0.00456 0.00717 -0.00170 C14 1 0.133029 0.462585 0.784371 11.00000 0.04657 0.03105 = 0.03180 -0.00565 0.01773 0.00352 AFIX 23 H14A 2 0.147585 0.338273 0.800804 11.00000 -1.20000 H14B 2 0.163075 0.533888 0.767584 11.00000 -1.20000 AFIX 0 C15 1 0.083540 0.447040 0.719479 11.00000 0.06443 0.04407 = 0.02950 -0.00768 0.00886 -0.00286 AFIX 137 H15A 2 0.054167 0.375738 0.736658 11.00000 -1.50000 H15B 2 0.094535 0.384410 0.675608 11.00000 -1.50000 H15C 2 0.069515 0.570792 0.703679 11.00000 -1.50000 AFIX 0 C16 1 0.170655 0.712094 1.044046 11.00000 0.02678 0.03775 = 0.02490 0.00603 -0.00156 -0.00289 AFIX 137 H16A 2 0.155319 0.784340 1.081908 11.00000 -1.50000 H16B 2 0.207829 0.758867 1.041278 11.00000 -1.50000 H16C 2 0.173430 0.582105 1.059801 11.00000 -1.50000 AFIX 0 C17 1 0.026821 1.112982 0.876242 11.00000 0.03260 0.02898 = 0.03769 0.00783 0.00951 0.00724 AFIX 137 H17A 2 -0.012915 1.083659 0.860020 11.00000 -1.50000 H17B 2 0.041702 1.153309 0.831341 11.00000 -1.50000 H17C 2 0.031463 1.212069 0.914794 11.00000 -1.50000 AFIX 0 HKLF 4 1 1 0 0 0 1 0 0 0 1 REM marc in C2/c REM R1 = 0.0451 for 2872 Fo > 4sig(Fo) and 0.0551 for all 3528 data REM 194 parameters refined using 0 restraints END WGHT 0.0668 1.6567 REM Instructions for potential hydrogen bonds HTAB O4 O3_$1 REM Highest difference peak 0.343, deepest hole -0.276, 1-sigma level 0.046 Q1 1 -0.0028 1.1437 0.9044 11.00000 0.05 0.34 Q2 1 0.0898 0.9359 0.9178 11.00000 0.05 0.33 Q3 1 0.1051 0.6883 0.9684 11.00000 0.05 0.31 Q4 1 0.0532 1.2122 0.8780 11.00000 0.05 0.30 ; _shelx_space_group_comment ; The symmetry employed for this shelxl refinement is uniquely defined by the following loop, which should always be used as a source of symmetry information in preference to the above space-group names. They are only intended as comments. ; _shelxl_version_number 2013-2 _space_group_IT_number 15 _space_group_crystal_system Monoclinic _space_group_name_H-M_alt 'C 1 2/c 1' _space_group_name_Hall '-C 2yc' loop_ _atom_type_description _atom_type_scat_dispersion_imag _atom_type_scat_dispersion_real _atom_type_scat_source _atom_type_symbol C 0.0016 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' C H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H O 0.0060 0.0106 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O loop_ _space_group_symop_operation_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' loop_ _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_calc_flag _atom_site_disorder_assembly _atom_site_disorder_group _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_label _atom_site_occupancy _atom_site_refinement_flags_adp _atom_site_refinement_flags_occupancy _atom_site_refinement_flags_posn _atom_site_site_symmetry_order _atom_site_type_symbol 0.0371(3) Uani d . . 0.20309(4) 0.55874(15) 0.91532(7) O1 1 . . . 1 O 0.0256(2) Uani d . . 0.11487(4) 0.55656(13) 0.84808(5) O2 1 . . . 1 O 0.0324(3) Uani d . . 0.06489(4) 0.51542(14) 1.00077(6) O3 1 . . . 1 O 0.0296(3) Uani d . . -0.02255(4) 0.77046(14) 0.92759(6) O4 1 . . . 1 O 0.044 Uiso calc . . -0.0283 0.6768 0.9530 H4A 1 U . R 1 H 0.0202(3) Uani d . . 0.12121(5) 0.93410(17) 0.93137(7) C1 1 . . . 1 C 0.0198(3) Uani d . . 0.13223(5) 0.72922(17) 0.96465(7) C2 1 . . . 1 C 0.0211(3) Uani d . . 0.07410(5) 0.65972(18) 0.96945(7) C3 1 . . . 1 C 0.0212(3) Uani d . . 0.03314(5) 0.79458(18) 0.93380(7) C4 1 . . . 1 C 0.0218(3) Uani d . . 0.05775(5) 0.94453(18) 0.91078(8) C5 1 . . . 1 C 0.0291(3) Uani d . . 0.11939(6) 0.93561(19) 0.78593(8) C6 1 . . . 1 C 0.035 Uiso calc . . 0.0814 0.8987 0.7776 H6A 1 U . R 1 H 0.0392(4) Uani d . . 0.14499(8) 0.9573(2) 0.72285(10) C7 1 . . . 1 C 0.047 Uiso calc . . 0.1245 0.9346 0.6721 H7A 1 U . R 1 H 0.0445(4) Uani d . . 0.20015(8) 1.0118(3) 0.73383(10) C8 1 . . . 1 C 0.053 Uiso calc . . 0.2177 1.0272 0.6908 H8A 1 U . R 1 H 0.0428(4) Uani d . . 0.22954(7) 1.0436(3) 0.80795(11) C9 1 . . . 1 C 0.051 Uiso calc . . 0.2675 1.0804 0.8158 H9A 1 U . R 1 H 0.0317(3) Uani d . . 0.20402(6) 1.0221(2) 0.87116(9) C10 1 . . . 1 C 0.038 Uiso calc . . 0.2247 1.0453 0.9217 H10 1 U . R 1 H 0.0226(3) Uani d . . 0.14840(6) 0.96691(17) 0.86107(8) C11 1 . . . 1 C 0.0304(3) Uani d . . 0.14100(6) 1.0817(2) 0.99373(9) C12 1 . . . 1 C 0.046 Uiso calc . . 0.1345 1.2049 0.9708 H12A 1 U . R 1 H 0.046 Uiso calc . . 0.1810 1.0655 1.0146 H12B 1 U . R 1 H 0.046 Uiso calc . . 0.1202 1.0685 1.0355 H12C 1 U . R 1 H 0.0222(3) Uani d . . 0.15511(5) 0.60549(17) 0.90770(8) C13 1 . . . 1 C 0.0351(4) Uani d . . 0.13303(7) 0.4626(2) 0.78437(9) C14 1 . . . 1 C 0.042 Uiso calc . . 0.1476 0.3383 0.8008 H14A 1 U . R 1 H 0.042 Uiso calc . . 0.1631 0.5339 0.7676 H14B 1 U . R 1 H 0.0461(4) Uani d . . 0.08354(9) 0.4470(3) 0.71948(10) C15 1 . . . 1 C 0.069 Uiso calc . . 0.0542 0.3757 0.7367 H15A 1 U . R 1 H 0.069 Uiso calc . . 0.0945 0.3844 0.6756 H15B 1 U . R 1 H 0.069 Uiso calc . . 0.0695 0.5708 0.7037 H15C 1 U . R 1 H 0.0307(3) Uani d . . 0.17066(6) 0.7121(2) 1.04405(8) C16 1 . . . 1 C 0.046 Uiso calc . . 0.1553 0.7843 1.0819 H16A 1 U . R 1 H 0.046 Uiso calc . . 0.2078 0.7589 1.0413 H16B 1 U . R 1 H 0.046 Uiso calc . . 0.1734 0.5821 1.0598 H16C 1 U . R 1 H 0.0327(3) Uani d . . 0.02682(6) 1.1130(2) 0.87624(9) C17 1 . . . 1 C 0.049 Uiso calc . . -0.0129 1.0837 0.8600 H17A 1 U . R 1 H 0.049 Uiso calc . . 0.0417 1.1533 0.8313 H17B 1 U . R 1 H 0.049 Uiso calc . . 0.0315 1.2121 0.9148 H17C 1 U . R 1 H loop_ _atom_site_aniso_U_11 _atom_site_aniso_U_12 _atom_site_aniso_U_13 _atom_site_aniso_U_22 _atom_site_aniso_U_23 _atom_site_aniso_U_33 _atom_site_aniso_label 0.0223(5) 0.0058(4) 0.0092(5) 0.0386(6) -0.0047(5) 0.0512(7) O1 0.0255(5) 0.0004(4) 0.0077(4) 0.0277(5) -0.0034(4) 0.0247(5) O2 0.0265(5) -0.0013(4) 0.0144(5) 0.0290(5) 0.0127(5) 0.0449(7) O3 0.0175(5) -0.0006(4) 0.0068(4) 0.0340(5) 0.0096(4) 0.0378(6) O4 0.0215(6) -0.0013(5) 0.0057(5) 0.0204(6) 0.0011(5) 0.0195(6) C1 0.0172(6) -0.0011(5) 0.0046(5) 0.0225(6) 0.0032(5) 0.0200(6) C2 0.0205(6) -0.0021(5) 0.0071(5) 0.0237(6) -0.0004(5) 0.0203(6) C3 0.0176(6) 0.0006(5) 0.0057(5) 0.0266(6) 0.0001(5) 0.0203(6) C4 0.0221(6) 0.0022(5) 0.0071(5) 0.0249(6) 0.0001(5) 0.0197(6) C5 0.0351(8) 0.0003(6) 0.0101(6) 0.0275(7) 0.0028(5) 0.0263(7) C6 0.0539(10) 0.0085(7) 0.0146(7) 0.0410(9) 0.0069(7) 0.0253(8) C7 0.0497(10) 0.0173(8) 0.0294(8) 0.0532(10) 0.0206(8) 0.0390(9) C8 0.0297(8) 0.0088(7) 0.0196(7) 0.0572(11) 0.0216(8) 0.0466(10) C9 0.0247(7) 0.0038(6) 0.0103(6) 0.0381(8) 0.0120(6) 0.0342(8) C10 0.0255(7) 0.0029(5) 0.0107(5) 0.0199(6) 0.0049(5) 0.0247(7) C11 0.0343(8) -0.0059(6) 0.0090(6) 0.0283(7) -0.0070(6) 0.0299(8) C12 0.0209(6) -0.0017(5) 0.0072(5) 0.0190(6) 0.0046(5) 0.0278(7) C13 0.0466(9) 0.0035(6) 0.0177(7) 0.0310(8) -0.0057(6) 0.0318(8) C14 0.0644(12) -0.0029(8) 0.0089(8) 0.0441(10) -0.0077(7) 0.0295(9) C15 0.0268(7) -0.0029(6) -0.0016(6) 0.0378(8) 0.0060(6) 0.0249(7) C16 0.0326(8) 0.0072(6) 0.0095(6) 0.0290(7) 0.0078(6) 0.0377(8) C17 loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_publ_flag _geom_bond_site_symmetry_2 O1 C13 1.2024(17) ? . O2 C13 1.3384(16) ? . O2 C14 1.4571(18) ? . O3 C3 1.2237(17) ? . O4 C4 1.3553(16) ? . O4 H4A 0.8400 ? . C1 C5 1.5235(18) ? . C1 C11 1.5381(18) ? . C1 C12 1.5419(19) ? . C1 C2 1.5987(18) ? . C2 C3 1.5255(17) ? . C2 C16 1.5301(18) ? . C2 C13 1.5328(19) ? . C3 C4 1.4500(18) ? . C4 C5 1.3427(18) ? . C5 C17 1.4995(19) ? . C6 C7 1.390(2) ? . C6 C11 1.393(2) ? . C6 H6A 0.9500 ? . C7 C8 1.381(3) ? . C7 H7A 0.9500 ? . C8 C9 1.382(3) ? . C8 H8A 0.9500 ? . C9 C10 1.391(2) ? . C9 H9A 0.9500 ? . C10 C11 1.394(2) ? . C10 H10 0.9500 ? . C12 H12A 0.9800 ? . C12 H12B 0.9800 ? . C12 H12C 0.9800 ? . C14 C15 1.497(2) ? . C14 H14A 0.9900 ? . C14 H14B 0.9900 ? . C15 H15A 0.9800 ? . C15 H15B 0.9800 ? . C15 H15C 0.9800 ? . C16 H16A 0.9800 ? . C16 H16B 0.9800 ? . C16 H16C 0.9800 ? . C17 H17A 0.9800 ? . C17 H17B 0.9800 ? . C17 H17C 0.9800 ? . loop_ _geom_angle _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle_publ_flag _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 116.24(11) C13 O2 C14 ? . . 109.5 C4 O4 H4A ? . . 112.46(11) C5 C1 C11 ? . . 107.26(11) C5 C1 C12 ? . . 110.16(11) C11 C1 C12 ? . . 102.89(10) C5 C1 C2 ? . . 111.82(10) C11 C1 C2 ? . . 111.99(11) C12 C1 C2 ? . . 109.39(11) C3 C2 C16 ? . . 107.97(10) C3 C2 C13 ? . . 108.43(11) C16 C2 C13 ? . . 103.62(10) C3 C2 C1 ? . . 116.11(11) C16 C2 C1 ? . . 110.98(10) C13 C2 C1 ? . . 126.74(12) O3 C3 C4 ? . . 124.30(12) O3 C3 C2 ? . . 108.93(11) C4 C3 C2 ? . . 125.65(12) C5 C4 O4 ? . . 111.33(11) C5 C4 C3 ? . . 122.99(12) O4 C4 C3 ? . . 124.11(12) C4 C5 C17 ? . . 112.57(11) C4 C5 C1 ? . . 123.02(12) C17 C5 C1 ? . . 121.30(15) C7 C6 C11 ? . . 119.3 C7 C6 H6A ? . . 119.3 C11 C6 H6A ? . . 120.10(16) C8 C7 C6 ? . . 119.9 C8 C7 H7A ? . . 119.9 C6 C7 H7A ? . . 119.36(15) C7 C8 C9 ? . . 120.3 C7 C8 H8A ? . . 120.3 C9 C8 H8A ? . . 120.65(16) C8 C9 C10 ? . . 119.7 C8 C9 H9A ? . . 119.7 C10 C9 H9A ? . . 120.70(15) C9 C10 C11 ? . . 119.7 C9 C10 H10 ? . . 119.7 C11 C10 H10 ? . . 117.89(13) C6 C11 C10 ? . . 121.57(12) C6 C11 C1 ? . . 120.50(12) C10 C11 C1 ? . . 109.5 C1 C12 H12A ? . . 109.5 C1 C12 H12B ? . . 109.5 H12A C12 H12B ? . . 109.5 C1 C12 H12C ? . . 109.5 H12A C12 H12C ? . . 109.5 H12B C12 H12C ? . . 124.19(13) O1 C13 O2 ? . . 124.46(13) O1 C13 C2 ? . . 111.35(11) O2 C13 C2 ? . . 107.61(14) O2 C14 C15 ? . . 110.2 O2 C14 H14A ? . . 110.2 C15 C14 H14A ? . . 110.2 O2 C14 H14B ? . . 110.2 C15 C14 H14B ? . . 108.5 H14A C14 H14B ? . . 109.5 C14 C15 H15A ? . . 109.5 C14 C15 H15B ? . . 109.5 H15A C15 H15B ? . . 109.5 C14 C15 H15C ? . . 109.5 H15A C15 H15C ? . . 109.5 H15B C15 H15C ? . . 109.5 C2 C16 H16A ? . . 109.5 C2 C16 H16B ? . . 109.5 H16A C16 H16B ? . . 109.5 C2 C16 H16C ? . . 109.5 H16A C16 H16C ? . . 109.5 H16B C16 H16C ? . . 109.5 C5 C17 H17A ? . . 109.5 C5 C17 H17B ? . . 109.5 H17A C17 H17B ? . . 109.5 C5 C17 H17C ? . . 109.5 H17A C17 H17C ? . . 109.5 H17B C17 H17C ? . . loop_ _geom_torsion _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_publ_flag _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 -7.79(12) C5 C1 C2 C3 ? . . . . -128.72(11) C11 C1 C2 C3 ? . . . . 107.09(12) C12 C1 C2 C3 ? . . . . -127.74(12) C5 C1 C2 C16 ? . . . . 111.33(13) C11 C1 C2 C16 ? . . . . -12.86(15) C12 C1 C2 C16 ? . . . . 107.86(11) C5 C1 C2 C13 ? . . . . -13.06(14) C11 C1 C2 C13 ? . . . . -137.26(11) C12 C1 C2 C13 ? . . . . -46.57(18) C16 C2 C3 O3 ? . . . . 71.24(16) C13 C2 C3 O3 ? . . . . -171.00(13) C1 C2 C3 O3 ? . . . . 131.43(12) C16 C2 C3 C4 ? . . . . -110.77(12) C13 C2 C3 C4 ? . . . . 7.00(13) C1 C2 C3 C4 ? . . . . 174.64(13) O3 C3 C4 C5 ? . . . . -3.29(15) C2 C3 C4 C5 ? . . . . -3.5(2) O3 C3 C4 O4 ? . . . . 178.59(11) C2 C3 C4 O4 ? . . . . 1.9(2) O4 C4 C5 C17 ? . . . . -176.16(13) C3 C4 C5 C17 ? . . . . 175.74(12) O4 C4 C5 C1 ? . . . . -2.32(16) C3 C4 C5 C1 ? . . . . 127.01(12) C11 C1 C5 C4 ? . . . . -111.72(13) C12 C1 C5 C4 ? . . . . 6.53(14) C2 C1 C5 C4 ? . . . . -59.06(16) C11 C1 C5 C17 ? . . . . 62.20(16) C12 C1 C5 C17 ? . . . . -179.55(12) C2 C1 C5 C17 ? . . . . -0.3(2) C11 C6 C7 C8 ? . . . . 0.3(3) C6 C7 C8 C9 ? . . . . -0.3(3) C7 C8 C9 C10 ? . . . . 0.4(3) C8 C9 C10 C11 ? . . . . 0.4(2) C7 C6 C11 C10 ? . . . . -176.99(13) C7 C6 C11 C1 ? . . . . -0.5(2) C9 C10 C11 C6 ? . . . . 176.97(14) C9 C10 C11 C1 ? . . . . -23.64(17) C5 C1 C11 C6 ? . . . . -143.24(13) C12 C1 C11 C6 ? . . . . 91.55(14) C2 C1 C11 C6 ? . . . . 159.01(12) C5 C1 C11 C10 ? . . . . 39.42(17) C12 C1 C11 C10 ? . . . . -85.79(15) C2 C1 C11 C10 ? . . . . -8.78(19) C14 O2 C13 O1 ? . . . . 170.95(11) C14 O2 C13 C2 ? . . . . -142.83(13) C3 C2 C13 O1 ? . . . . -24.41(17) C16 C2 C13 O1 ? . . . . 104.24(15) C1 C2 C13 O1 ? . . . . 37.44(14) C3 C2 C13 O2 ? . . . . 155.86(11) C16 C2 C13 O2 ? . . . . -75.49(13) C1 C2 C13 O2 ? . . . . -171.29(12) C13 O2 C14 C15 ? . . . . loop_ _geom_hbond_angle_DHA _geom_hbond_atom_site_label_A _geom_hbond_atom_site_label_D _geom_hbond_atom_site_label_H _geom_hbond_distance_DA _geom_hbond_distance_DH _geom_hbond_distance_HA _geom_hbond_site_symmetry_A 162.4 O3 O4 H4A 2.7340(15) 0.84 1.92 '5_567'