data_shelxl_4 loop_ _journal_name_full 'European Journal of Chemistry' _journal_coden_ASTM EJCUA9 _journal_volume 8 _journal_issue 1 _journal_year 2017 _journal_page_first 33 _journal_page_last 41 _audit_update_record ; 2016-12-03 # Formatted by publCIF ; _publcif_datablock.id '{e47e116c-60a1-43be-9d6b-ebf9155e0872}' # publcif _publ_body_element loop start loop_ _publ_body_element _publ_body_title _publ_body_contents section ; Chemical context ; ; ; section ; Structural commentary ; ; ; section ; Supramolecular features ; ; ; section ; Database survey ; ; ; section ; Synthesis and crystallization ; ; ; section ; Refinement ; ; Crystal data, data collection and structure refinement details are summarized in Table 1. ; # publcif _publ_body_element loop end _audit_creation_method SHELXL-97 _chemical_name_systematic ? _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C19 H16 O4' _chemical_formula_sum 'C19 H16 O4' _chemical_formula_weight 308.32 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' _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M 'P 1 21/c 1' _symmetry_space_group_name_Hall '-P 2ybc' _symmetry_Int_Tables_number 14 loop_ _symmetry_equiv_pos_site_id _symmetry_equiv_pos_as_xyz 1 '+X,+Y,+Z' 2 '-X,1/2+Y,1/2-Z' 3 '-X,-Y,-Z' 4 '+X,1/2-Y,1/2+Z' _cell_length_a 7.88320(10) _cell_length_b 15.9187(3) _cell_length_c 24.6606(4) _cell_angle_alpha 90.00 _cell_angle_beta 92.6120(10) _cell_angle_gamma 90.00 _cell_volume 3091.45(9) _cell_formula_units_Z 8 _cell_measurement_temperature 193(2) _cell_measurement_reflns_used 45924 _cell_measurement_theta_min 3.31 _cell_measurement_theta_max 68.23 _exptl_crystal_description platelet _exptl_crystal_colour colorless _exptl_crystal_size_max 0.50 _exptl_crystal_size_mid 0.20 _exptl_crystal_size_min 0.10 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.325 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1296 _exptl_absorpt_coefficient_mu 0.759 _exptl_absorpt_correction_type numerical _exptl_absorpt_correction_T_min 0.7026 _exptl_absorpt_correction_T_max 0.9279 _exptl_absorpt_process_details ; NUMABUS (Higashi, 1999) ; _diffrn_ambient_temperature 193(2) _diffrn_radiation_wavelength 1.54187 _diffrn_radiation_type CuK\a _diffrn_radiation_source 'rotating anode' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Rigaku R-AXIS RAPID' _diffrn_measurement_method \w _diffrn_detector_area_resol_mean 10.000 _diffrn_reflns_number 56413 _diffrn_reflns_av_R_equivalents 0.0487 _diffrn_reflns_av_sigmaI/netI 0.0280 _diffrn_reflns_limit_h_min -9 _diffrn_reflns_limit_h_max 9 _diffrn_reflns_limit_k_min -19 _diffrn_reflns_limit_k_max 19 _diffrn_reflns_limit_l_min -29 _diffrn_reflns_limit_l_max 29 _diffrn_reflns_theta_min 3.31 _diffrn_reflns_theta_max 68.25 _reflns_number_total 5667 _reflns_number_gt 4390 _reflns_threshold_expression >2sigma(I) _computing_data_collection ? _computing_cell_refinement ? _computing_data_reduction ? _computing_structure_solution ? _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics ? _computing_publication_material ? _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0812P)^2^+0.1482P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment constr _refine_ls_extinction_method SHELXL _refine_ls_extinction_coef 0.0021(2) _refine_ls_extinction_expression 'Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^' _refine_ls_number_reflns 5667 _refine_ls_number_parameters 422 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0521 _refine_ls_R_factor_gt 0.0427 _refine_ls_wR_factor_ref 0.1302 _refine_ls_wR_factor_gt 0.1219 _refine_ls_goodness_of_fit_ref 1.022 _refine_ls_restrained_S_all 1.022 _refine_ls_shift/su_max 0.000 _refine_ls_shift/su_mean 0.000 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 _atom_site_disorder_assembly _atom_site_disorder_group O1 O 0.38530(13) 0.59712(7) 0.37606(5) 0.0528(3) Uani 1 1 d . . . O2 O 0.14182(14) 0.44481(7) 0.44475(4) 0.0493(3) Uani 1 1 d . . . O3 O 0.51900(16) 0.50136(8) 0.18444(5) 0.0567(3) Uani 1 1 d . . . O4 O -0.37508(14) 0.72353(7) 0.38779(5) 0.0547(3) Uani 1 1 d . . . H39 H -0.4562 0.6898 0.3828 0.082 Uiso 1 1 calc R . . O5 O 0.89380(13) 0.14982(8) 0.48648(5) 0.0543(3) Uani 1 1 d . . . O6 O 0.64587(15) 0.32873(7) 0.47307(5) 0.0543(3) Uani 1 1 d . . . O7 O 1.01658(16) 0.02267(8) 0.29604(5) 0.0621(4) Uani 1 1 d . . . O8 O 0.13789(14) 0.05859(8) 0.54298(5) 0.0548(3) Uani 1 1 d . . . H40 H 0.0552 0.0781 0.5243 0.082 Uiso 1 1 calc R . . C1 C 0.25089(18) 0.46620(10) 0.35953(6) 0.0387(4) Uani 1 1 d . . . C2 C 0.18958(19) 0.41027(10) 0.39696(6) 0.0417(4) Uani 1 1 d . . . C3 C 0.1812(2) 0.32403(10) 0.38612(7) 0.0469(4) Uani 1 1 d . . . H3 H 0.1416 0.2862 0.4125 0.056 Uiso 1 1 calc R . . C4 C 0.2307(2) 0.29490(11) 0.33717(7) 0.0485(4) Uani 1 1 d . . . H4 H 0.2204 0.2366 0.3293 0.058 Uiso 1 1 calc R . . C5 C 0.2964(2) 0.34877(10) 0.29799(7) 0.0435(4) Uani 1 1 d . . . C6 C 0.3495(2) 0.31867(11) 0.24733(7) 0.0522(4) Uani 1 1 d . . . H6 H 0.3355 0.2608 0.2387 0.063 Uiso 1 1 calc R . . C7 C 0.4196(2) 0.37042(11) 0.21090(7) 0.0538(4) Uani 1 1 d . . . H7 H 0.4542 0.3491 0.1772 0.065 Uiso 1 1 calc R . . C8 C 0.4408(2) 0.45653(11) 0.22361(6) 0.0461(4) Uani 1 1 d . . . C9 C 0.38645(19) 0.48914(10) 0.27084(6) 0.0413(4) Uani 1 1 d . . . H9 H 0.3984 0.5475 0.2780 0.050 Uiso 1 1 calc R . . C10 C 0.31180(18) 0.43592(9) 0.30950(6) 0.0383(3) Uani 1 1 d . . . C11 C 0.25025(19) 0.55847(10) 0.37173(6) 0.0386(4) Uani 1 1 d . . . C12 C 0.08572(18) 0.60102(9) 0.37589(6) 0.0371(3) Uani 1 1 d . . . C13 C -0.06551(18) 0.55984(10) 0.36106(6) 0.0396(4) Uani 1 1 d . . . H13 H -0.0620 0.5033 0.3489 0.048 Uiso 1 1 calc R . . C14 C -0.22000(19) 0.59980(10) 0.36378(6) 0.0418(4) Uani 1 1 d . . . H14 H -0.3219 0.5712 0.3531 0.050 Uiso 1 1 calc R . . C15 C -0.22590(19) 0.68228(10) 0.38222(6) 0.0422(4) Uani 1 1 d . . . C16 C -0.0765(2) 0.72472(10) 0.39650(7) 0.0466(4) Uani 1 1 d . . . H16 H -0.0804 0.7815 0.4083 0.056 Uiso 1 1 calc R . . C17 C 0.0774(2) 0.68435(10) 0.39346(6) 0.0436(4) Uani 1 1 d . . . H17 H 0.1792 0.7135 0.4034 0.052 Uiso 1 1 calc R . . C18 C 0.0958(2) 0.38905(12) 0.48712(7) 0.0576(5) Uani 1 1 d . . . H18A H -0.0039 0.3562 0.4749 0.069 Uiso 1 1 calc R . . H18B H 0.0691 0.4217 0.5193 0.069 Uiso 1 1 calc R . . H18C H 0.1907 0.3510 0.4962 0.069 Uiso 1 1 calc R . . C19 C 0.5630(2) 0.58601(12) 0.19658(7) 0.0559(5) Uani 1 1 d . . . H19A H 0.6364 0.5878 0.2297 0.067 Uiso 1 1 calc R . . H19B H 0.4596 0.6185 0.2020 0.067 Uiso 1 1 calc R . . H19C H 0.6234 0.6101 0.1664 0.067 Uiso 1 1 calc R . . C20 C 0.75375(18) 0.22752(10) 0.41636(6) 0.0398(4) Uani 1 1 d . . . C21 C 0.6933(2) 0.30860(10) 0.42200(7) 0.0442(4) Uani 1 1 d . . . C22 C 0.6855(2) 0.36482(11) 0.37844(8) 0.0509(4) Uani 1 1 d . . . H22 H 0.6439 0.4203 0.3831 0.061 Uiso 1 1 calc R . . C23 C 0.7382(2) 0.33905(11) 0.32920(7) 0.0531(4) Uani 1 1 d . . . H23 H 0.7303 0.3769 0.2994 0.064 Uiso 1 1 calc R . . C24 C 0.8042(2) 0.25777(11) 0.32122(7) 0.0470(4) Uani 1 1 d . . . C25 C 0.8639(2) 0.23166(13) 0.27077(7) 0.0579(5) Uani 1 1 d . . . H25 H 0.8555 0.2690 0.2407 0.069 Uiso 1 1 calc R . . C26 C 0.9328(2) 0.15472(13) 0.26432(7) 0.0588(5) Uani 1 1 d . . . H26 H 0.9744 0.1390 0.2302 0.071 Uiso 1 1 calc R . . C27 C 0.9431(2) 0.09769(11) 0.30819(7) 0.0501(4) Uani 1 1 d . . . C28 C 0.88408(19) 0.11919(10) 0.35790(6) 0.0436(4) Uani 1 1 d . . . H28 H 0.8897 0.0799 0.3869 0.052 Uiso 1 1 calc R . . C29 C 0.81443(19) 0.20059(10) 0.36572(6) 0.0415(4) Uani 1 1 d . . . C30 C 0.75627(19) 0.17049(10) 0.46497(6) 0.0403(4) Uani 1 1 d . . . C31 C 0.59401(18) 0.14147(10) 0.48499(6) 0.0388(4) Uani 1 1 d . . . C32 C 0.44188(19) 0.15645(10) 0.45531(6) 0.0411(4) Uani 1 1 d . . . H32 H 0.4438 0.1863 0.4220 0.049 Uiso 1 1 calc R . . C33 C 0.2891(2) 0.12862(10) 0.47353(6) 0.0435(4) Uani 1 1 d . . . H33 H 0.1869 0.1383 0.4525 0.052 Uiso 1 1 calc R . . C34 C 0.2854(2) 0.08643(10) 0.52271(6) 0.0424(4) Uani 1 1 d . . . C35 C 0.4356(2) 0.07108(10) 0.55317(6) 0.0449(4) Uani 1 1 d . . . H35 H 0.4330 0.0421 0.5868 0.054 Uiso 1 1 calc R . . C36 C 0.5873(2) 0.09814(10) 0.53417(6) 0.0430(4) Uani 1 1 d . . . H36 H 0.6896 0.0872 0.5548 0.052 Uiso 1 1 calc R . . C37 C 0.5872(3) 0.41158(12) 0.48251(8) 0.0648(5) Uani 1 1 d . . . H37A H 0.4867 0.4229 0.4588 0.078 Uiso 1 1 calc R . . H37B H 0.6768 0.4519 0.4748 0.078 Uiso 1 1 calc R . . H37C H 0.5576 0.4171 0.5205 0.078 Uiso 1 1 calc R . . C38 C 1.0293(3) -0.03925(13) 0.33736(9) 0.0780(6) Uani 1 1 d . . . H38A H 0.9153 -0.0546 0.3482 0.094 Uiso 1 1 calc R . . H38B H 1.0950 -0.0168 0.3688 0.094 Uiso 1 1 calc R . . H38C H 1.0865 -0.0891 0.3236 0.094 Uiso 1 1 calc 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 O1 0.0315(6) 0.0577(7) 0.0694(8) -0.0127(6) 0.0056(5) -0.0077(5) O2 0.0502(7) 0.0549(7) 0.0435(6) 0.0049(5) 0.0078(5) -0.0004(5) O3 0.0673(8) 0.0582(7) 0.0454(7) -0.0029(5) 0.0121(6) -0.0080(6) O4 0.0374(7) 0.0431(6) 0.0840(9) 0.0020(6) 0.0081(6) 0.0048(5) O5 0.0333(6) 0.0701(8) 0.0593(7) 0.0056(6) -0.0010(5) 0.0084(5) O6 0.0562(7) 0.0464(7) 0.0607(8) -0.0093(5) 0.0062(6) 0.0073(5) O7 0.0608(8) 0.0647(8) 0.0618(8) -0.0150(6) 0.0147(6) 0.0033(6) O8 0.0399(7) 0.0628(8) 0.0624(8) 0.0177(6) 0.0101(6) 0.0031(6) C1 0.0286(8) 0.0446(9) 0.0426(8) 0.0009(7) -0.0013(6) 0.0015(6) C2 0.0316(8) 0.0499(9) 0.0433(9) 0.0032(7) 0.0000(6) 0.0023(7) C3 0.0394(9) 0.0467(9) 0.0542(10) 0.0096(7) -0.0010(7) -0.0017(7) C4 0.0416(9) 0.0421(9) 0.0613(11) 0.0027(8) -0.0039(8) -0.0013(7) C5 0.0378(9) 0.0425(8) 0.0497(9) -0.0011(7) -0.0028(7) 0.0013(7) C6 0.0572(11) 0.0433(9) 0.0557(10) -0.0076(8) -0.0006(8) 0.0002(8) C7 0.0598(11) 0.0531(10) 0.0488(10) -0.0106(8) 0.0041(8) 0.0020(8) C8 0.0431(9) 0.0522(10) 0.0430(9) 0.0002(7) 0.0021(7) -0.0006(7) C9 0.0372(9) 0.0432(9) 0.0432(9) -0.0013(7) -0.0001(7) 0.0011(7) C10 0.0291(8) 0.0424(8) 0.0430(8) -0.0003(6) -0.0026(6) 0.0019(6) C11 0.0329(8) 0.0464(9) 0.0365(8) -0.0013(6) 0.0024(6) -0.0028(7) C12 0.0322(8) 0.0421(8) 0.0370(8) 0.0019(6) 0.0030(6) -0.0021(6) C13 0.0341(8) 0.0407(8) 0.0440(9) 0.0002(6) 0.0016(6) -0.0024(6) C14 0.0327(8) 0.0423(9) 0.0503(9) 0.0031(7) 0.0008(7) -0.0030(6) C15 0.0348(8) 0.0419(9) 0.0503(9) 0.0058(7) 0.0071(7) 0.0032(7) C16 0.0432(10) 0.0384(8) 0.0588(10) -0.0018(7) 0.0081(7) -0.0018(7) C17 0.0375(9) 0.0428(9) 0.0507(9) -0.0029(7) 0.0047(7) -0.0068(7) C18 0.0552(11) 0.0708(12) 0.0471(10) 0.0123(8) 0.0070(8) -0.0102(9) C19 0.0582(11) 0.0566(11) 0.0534(10) 0.0039(8) 0.0085(8) -0.0057(9) C20 0.0302(8) 0.0429(8) 0.0462(9) -0.0008(7) 0.0018(6) -0.0012(6) C21 0.0333(8) 0.0442(9) 0.0548(10) -0.0029(7) 0.0004(7) -0.0020(7) C22 0.0418(10) 0.0416(9) 0.0689(12) 0.0034(8) -0.0031(8) -0.0023(7) C23 0.0460(10) 0.0512(10) 0.0613(11) 0.0113(8) -0.0062(8) -0.0062(8) C24 0.0387(9) 0.0540(10) 0.0479(9) 0.0032(7) -0.0027(7) -0.0084(7) C25 0.0560(11) 0.0710(13) 0.0463(10) 0.0056(9) -0.0012(8) -0.0112(9) C26 0.0558(11) 0.0771(13) 0.0437(10) -0.0080(9) 0.0050(8) -0.0105(10) C27 0.0419(9) 0.0572(11) 0.0515(10) -0.0127(8) 0.0045(7) -0.0052(8) C28 0.0362(9) 0.0480(9) 0.0468(9) -0.0033(7) 0.0045(7) -0.0039(7) C29 0.0307(8) 0.0476(9) 0.0458(9) -0.0011(7) -0.0007(6) -0.0062(7) C30 0.0339(8) 0.0434(9) 0.0435(9) -0.0057(7) 0.0007(6) 0.0055(6) C31 0.0350(8) 0.0413(8) 0.0402(8) -0.0011(6) 0.0026(6) 0.0054(6) C32 0.0351(8) 0.0465(9) 0.0417(8) 0.0048(7) 0.0013(6) 0.0042(7) C33 0.0342(8) 0.0494(9) 0.0467(9) 0.0077(7) 0.0010(7) 0.0055(7) C34 0.0376(9) 0.0421(8) 0.0481(9) 0.0027(7) 0.0081(7) 0.0046(7) C35 0.0453(10) 0.0472(9) 0.0424(9) 0.0056(7) 0.0038(7) 0.0081(7) C36 0.0398(9) 0.0470(9) 0.0419(9) 0.0005(7) -0.0020(7) 0.0079(7) C37 0.0600(12) 0.0557(11) 0.0774(13) -0.0202(9) -0.0102(10) 0.0166(9) C38 0.0918(17) 0.0603(13) 0.0840(15) -0.0057(11) 0.0261(13) 0.0152(12) _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. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag O1 C11 1.2300(17) . ? O2 C2 1.3686(18) . ? O2 C18 1.4304(19) . ? O3 C8 1.3700(19) . ? O3 C19 1.420(2) . ? O4 C15 1.3593(18) . ? O4 H39 0.8400 . ? O5 C30 1.2299(18) . ? O6 C21 1.3678(19) . ? O6 C37 1.420(2) . ? O7 C27 1.366(2) . ? O7 C38 1.418(2) . ? O8 C34 1.3606(19) . ? O8 H40 0.8400 . ? C1 C2 1.385(2) . ? C1 C10 1.428(2) . ? C1 C11 1.499(2) . ? C2 C3 1.400(2) . ? C3 C4 1.367(2) . ? C3 H3 0.9500 . ? C4 C5 1.408(2) . ? C4 H4 0.9500 . ? C5 C6 1.419(2) . ? C5 C10 1.420(2) . ? C6 C7 1.355(2) . ? C6 H6 0.9500 . ? C7 C8 1.414(2) . ? C7 H7 0.9500 . ? C8 C9 1.362(2) . ? C9 C10 1.423(2) . ? C9 H9 0.9500 . ? C11 C12 1.471(2) . ? C12 C13 1.395(2) . ? C12 C17 1.398(2) . ? C13 C14 1.378(2) . ? C13 H13 0.9500 . ? C14 C15 1.391(2) . ? C14 H14 0.9500 . ? C15 C16 1.389(2) . ? C16 C17 1.378(2) . ? C16 H16 0.9500 . ? C17 H17 0.9500 . ? C18 H18A 0.9800 . ? C18 H18B 0.9800 . ? C18 H18C 0.9800 . ? C19 H19A 0.9800 . ? C19 H19B 0.9800 . ? C19 H19C 0.9800 . ? C20 C21 1.385(2) . ? C20 C29 1.424(2) . ? C20 C30 1.503(2) . ? C21 C22 1.397(2) . ? C22 C23 1.365(2) . ? C22 H22 0.9500 . ? C23 C24 1.412(2) . ? C23 H23 0.9500 . ? C24 C25 1.413(2) . ? C24 C29 1.425(2) . ? C25 C26 1.352(3) . ? C25 H25 0.9500 . ? C26 C27 1.412(3) . ? C26 H26 0.9500 . ? C27 C28 1.374(2) . ? C28 C29 1.424(2) . ? C28 H28 0.9500 . ? C30 C31 1.467(2) . ? C31 C32 1.397(2) . ? C31 C36 1.398(2) . ? C32 C33 1.377(2) . ? C32 H32 0.9500 . ? C33 C34 1.388(2) . ? C33 H33 0.9500 . ? C34 C35 1.395(2) . ? C35 C36 1.373(2) . ? C35 H35 0.9500 . ? C36 H36 0.9500 . ? C37 H37A 0.9800 . ? C37 H37B 0.9800 . ? C37 H37C 0.9800 . ? C38 H38A 0.9800 . ? C38 H38B 0.9800 . ? C38 H38C 0.9800 . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C2 O2 C18 117.94(13) . . ? C8 O3 C19 117.34(13) . . ? C15 O4 H39 109.5 . . ? C21 O6 C37 118.24(14) . . ? C27 O7 C38 117.83(14) . . ? C34 O8 H40 109.5 . . ? C2 C1 C10 120.00(14) . . ? C2 C1 C11 119.44(14) . . ? C10 C1 C11 120.56(13) . . ? O2 C2 C1 115.69(14) . . ? O2 C2 C3 123.10(14) . . ? C1 C2 C3 121.20(15) . . ? C4 C3 C2 119.26(15) . . ? C4 C3 H3 120.4 . . ? C2 C3 H3 120.4 . . ? C3 C4 C5 121.88(16) . . ? C3 C4 H4 119.1 . . ? C5 C4 H4 119.1 . . ? C4 C5 C6 122.07(15) . . ? C4 C5 C10 119.24(15) . . ? C6 C5 C10 118.70(15) . . ? C7 C6 C5 121.59(16) . . ? C7 C6 H6 119.2 . . ? C5 C6 H6 119.2 . . ? C6 C7 C8 119.32(16) . . ? C6 C7 H7 120.3 . . ? C8 C7 H7 120.3 . . ? C9 C8 O3 125.00(15) . . ? C9 C8 C7 121.37(16) . . ? O3 C8 C7 113.63(14) . . ? C8 C9 C10 120.13(15) . . ? C8 C9 H9 119.9 . . ? C10 C9 H9 119.9 . . ? C5 C10 C9 118.80(14) . . ? C5 C10 C1 118.27(14) . . ? C9 C10 C1 122.93(14) . . ? O1 C11 C12 121.74(14) . . ? O1 C11 C1 119.78(14) . . ? C12 C11 C1 118.43(13) . . ? C13 C12 C17 118.41(14) . . ? C13 C12 C11 120.74(14) . . ? C17 C12 C11 120.83(14) . . ? C14 C13 C12 121.13(14) . . ? C14 C13 H13 119.4 . . ? C12 C13 H13 119.4 . . ? C13 C14 C15 119.63(14) . . ? C13 C14 H14 120.2 . . ? C15 C14 H14 120.2 . . ? O4 C15 C16 117.85(14) . . ? O4 C15 C14 122.06(14) . . ? C16 C15 C14 120.08(14) . . ? C17 C16 C15 119.86(15) . . ? C17 C16 H16 120.1 . . ? C15 C16 H16 120.1 . . ? C16 C17 C12 120.87(15) . . ? C16 C17 H17 119.6 . . ? C12 C17 H17 119.6 . . ? O2 C18 H18A 109.5 . . ? O2 C18 H18B 109.5 . . ? H18A C18 H18B 109.5 . . ? O2 C18 H18C 109.5 . . ? H18A C18 H18C 109.5 . . ? H18B C18 H18C 109.5 . . ? O3 C19 H19A 109.5 . . ? O3 C19 H19B 109.5 . . ? H19A C19 H19B 109.5 . . ? O3 C19 H19C 109.5 . . ? H19A C19 H19C 109.5 . . ? H19B C19 H19C 109.5 . . ? C21 C20 C29 119.98(14) . . ? C21 C20 C30 118.34(14) . . ? C29 C20 C30 121.67(13) . . ? O6 C21 C20 114.87(14) . . ? O6 C21 C22 123.60(15) . . ? C20 C21 C22 121.52(16) . . ? C23 C22 C21 119.15(16) . . ? C23 C22 H22 120.4 . . ? C21 C22 H22 120.4 . . ? C22 C23 C24 121.92(16) . . ? C22 C23 H23 119.0 . . ? C24 C23 H23 119.0 . . ? C23 C24 C25 122.15(16) . . ? C23 C24 C29 119.10(16) . . ? C25 C24 C29 118.73(17) . . ? C26 C25 C24 121.47(17) . . ? C26 C25 H25 119.3 . . ? C24 C25 H25 119.3 . . ? C25 C26 C27 120.10(17) . . ? C25 C26 H26 119.9 . . ? C27 C26 H26 119.9 . . ? O7 C27 C28 125.27(16) . . ? O7 C27 C26 113.83(15) . . ? C28 C27 C26 120.89(17) . . ? C27 C28 C29 119.72(16) . . ? C27 C28 H28 120.1 . . ? C29 C28 H28 120.1 . . ? C20 C29 C28 122.67(14) . . ? C20 C29 C24 118.28(15) . . ? C28 C29 C24 119.05(15) . . ? O5 C30 C31 122.40(14) . . ? O5 C30 C20 119.01(14) . . ? C31 C30 C20 118.59(13) . . ? C32 C31 C36 118.22(14) . . ? C32 C31 C30 120.74(14) . . ? C36 C31 C30 121.03(14) . . ? C33 C32 C31 121.13(15) . . ? C33 C32 H32 119.4 . . ? C31 C32 H32 119.4 . . ? C32 C33 C34 119.62(15) . . ? C32 C33 H33 120.2 . . ? C34 C33 H33 120.2 . . ? O8 C34 C33 122.09(14) . . ? O8 C34 C35 117.63(14) . . ? C33 C34 C35 120.28(15) . . ? C36 C35 C34 119.49(15) . . ? C36 C35 H35 120.3 . . ? C34 C35 H35 120.3 . . ? C35 C36 C31 121.25(14) . . ? C35 C36 H36 119.4 . . ? C31 C36 H36 119.4 . . ? O6 C37 H37A 109.5 . . ? O6 C37 H37B 109.5 . . ? H37A C37 H37B 109.5 . . ? O6 C37 H37C 109.5 . . ? H37A C37 H37C 109.5 . . ? H37B C37 H37C 109.5 . . ? O7 C38 H38A 109.5 . . ? O7 C38 H38B 109.5 . . ? H38A C38 H38B 109.5 . . ? O7 C38 H38C 109.5 . . ? H38A C38 H38C 109.5 . . ? H38B C38 H38C 109.5 . . ? 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_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag C18 O2 C2 C1 -173.08(13) . . . . ? C18 O2 C2 C3 5.7(2) . . . . ? C10 C1 C2 O2 176.93(12) . . . . ? C11 C1 C2 O2 -3.9(2) . . . . ? C10 C1 C2 C3 -1.9(2) . . . . ? C11 C1 C2 C3 177.23(14) . . . . ? O2 C2 C3 C4 179.64(14) . . . . ? C1 C2 C3 C4 -1.6(2) . . . . ? C2 C3 C4 C5 2.6(2) . . . . ? C3 C4 C5 C6 179.36(15) . . . . ? C3 C4 C5 C10 -0.1(2) . . . . ? C4 C5 C6 C7 -177.00(16) . . . . ? C10 C5 C6 C7 2.5(2) . . . . ? C5 C6 C7 C8 0.1(3) . . . . ? C19 O3 C8 C9 7.1(2) . . . . ? C19 O3 C8 C7 -172.90(15) . . . . ? C6 C7 C8 C9 -2.5(3) . . . . ? C6 C7 C8 O3 177.59(16) . . . . ? O3 C8 C9 C10 -177.87(14) . . . . ? C7 C8 C9 C10 2.2(2) . . . . ? C4 C5 C10 C9 176.80(14) . . . . ? C6 C5 C10 C9 -2.7(2) . . . . ? C4 C5 C10 C1 -3.4(2) . . . . ? C6 C5 C10 C1 177.17(14) . . . . ? C8 C9 C10 C5 0.4(2) . . . . ? C8 C9 C10 C1 -179.42(14) . . . . ? C2 C1 C10 C5 4.3(2) . . . . ? C11 C1 C10 C5 -174.78(14) . . . . ? C2 C1 C10 C9 -175.83(14) . . . . ? C11 C1 C10 C9 5.0(2) . . . . ? C2 C1 C11 O1 117.27(16) . . . . ? C10 C1 C11 O1 -63.6(2) . . . . ? C2 C1 C11 C12 -65.29(18) . . . . ? C10 C1 C11 C12 113.84(15) . . . . ? O1 C11 C12 C13 168.06(14) . . . . ? C1 C11 C12 C13 -9.3(2) . . . . ? O1 C11 C12 C17 -10.3(2) . . . . ? C1 C11 C12 C17 172.34(14) . . . . ? C17 C12 C13 C14 -0.3(2) . . . . ? C11 C12 C13 C14 -178.65(14) . . . . ? C12 C13 C14 C15 -0.8(2) . . . . ? C13 C14 C15 O4 -177.30(14) . . . . ? C13 C14 C15 C16 1.6(2) . . . . ? O4 C15 C16 C17 177.57(14) . . . . ? C14 C15 C16 C17 -1.4(2) . . . . ? C15 C16 C17 C12 0.3(2) . . . . ? C13 C12 C17 C16 0.5(2) . . . . ? C11 C12 C17 C16 178.88(14) . . . . ? C37 O6 C21 C20 178.16(14) . . . . ? C37 O6 C21 C22 -0.7(2) . . . . ? C29 C20 C21 O6 -177.04(13) . . . . ? C30 C20 C21 O6 1.8(2) . . . . ? C29 C20 C21 C22 1.9(2) . . . . ? C30 C20 C21 C22 -179.30(14) . . . . ? O6 C21 C22 C23 179.00(15) . . . . ? C20 C21 C22 C23 0.2(2) . . . . ? C21 C22 C23 C24 -1.5(2) . . . . ? C22 C23 C24 C25 -177.97(16) . . . . ? C22 C23 C24 C29 0.7(2) . . . . ? C23 C24 C25 C26 177.41(17) . . . . ? C29 C24 C25 C26 -1.2(3) . . . . ? C24 C25 C26 C27 1.4(3) . . . . ? C38 O7 C27 C28 1.8(3) . . . . ? C38 O7 C27 C26 -178.77(18) . . . . ? C25 C26 C27 O7 -179.57(16) . . . . ? C25 C26 C27 C28 -0.1(3) . . . . ? O7 C27 C28 C29 178.18(15) . . . . ? C26 C27 C28 C29 -1.2(2) . . . . ? C21 C20 C29 C28 177.56(14) . . . . ? C30 C20 C29 C28 -1.2(2) . . . . ? C21 C20 C29 C24 -2.6(2) . . . . ? C30 C20 C29 C24 178.61(14) . . . . ? C27 C28 C29 C20 -178.86(14) . . . . ? C27 C28 C29 C24 1.3(2) . . . . ? C23 C24 C29 C20 1.4(2) . . . . ? C25 C24 C29 C20 -179.95(14) . . . . ? C23 C24 C29 C28 -178.79(14) . . . . ? C25 C24 C29 C28 -0.1(2) . . . . ? C21 C20 C30 O5 -111.04(17) . . . . ? C29 C20 C30 O5 67.8(2) . . . . ? C21 C20 C30 C31 68.99(19) . . . . ? C29 C20 C30 C31 -112.20(16) . . . . ? O5 C30 C31 C32 -171.01(14) . . . . ? C20 C30 C31 C32 9.0(2) . . . . ? O5 C30 C31 C36 9.0(2) . . . . ? C20 C30 C31 C36 -171.06(14) . . . . ? C36 C31 C32 C33 -0.7(2) . . . . ? C30 C31 C32 C33 179.29(14) . . . . ? C31 C32 C33 C34 1.3(2) . . . . ? C32 C33 C34 O8 179.09(15) . . . . ? C32 C33 C34 C35 -1.0(2) . . . . ? O8 C34 C35 C36 -179.99(14) . . . . ? C33 C34 C35 C36 0.1(2) . . . . ? C34 C35 C36 C31 0.5(2) . . . . ? C32 C31 C36 C35 -0.2(2) . . . . ? C30 C31 C36 C35 179.79(14) . . . . ? _diffrn_measured_fraction_theta_max 0.999 _diffrn_reflns_theta_full 68.25 _diffrn_measured_fraction_theta_full 0.999 _refine_diff_density_max 0.180 _refine_diff_density_min -0.174 _refine_diff_density_rms 0.042 loop_ _publcif_info_datablock.id _publcif_info_datablock.publ_exptl _publcif_info_datablock.publ_geom _publcif_info_datablock.structure '{e47e116c-60a1-43be-9d6b-ebf9155e0872}' y y y loop_ _publcif_info_exptl_table_extra_item sin_theta_over_lambda_max loop_ _publcif_info_exptl_table_header_item ? _publcif_info_exptl_table_max_cols 4 _publcif_info_exptl_table_use_headnotes n loop_ _publcif_info_tables.block_id _publcif_info_tables.reference_item "{e47e116c-60a1-43be-9d6b-ebf9155e0872}" "_publcif_info_datablock.publ_exptl" loop_ _publcif_info_cif.paper_type EE