data_song8cult _audit_creation_date 2014-06-11 _audit_creation_method ; Olex2 1.2-beta (compiled May 9 2012 12:37:22, GUI svn.r4230) ; _publ_contact_author_address ? _publ_contact_author_email ? _publ_contact_author_name '' _publ_contact_author_phone ? _chemical_name_common ? _chemical_name_systematic ; ? ; _chemical_formula_moiety 'C16 H16 O4' _chemical_formula_sum 'C16 H16 O4' _chemical_formula_weight 272.29 _chemical_melting_point ? 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 P2(1)/n _space_group_IT_number 14 _space_group_name_Hall '-P 2yn' loop_ _space_group_symop_id _space_group_symop_operation_xyz 1 'x, y, z' 2 '-x+1/2, y+1/2, -z+1/2' 3 '-x, -y, -z' 4 'x-1/2, -y-1/2, z-1/2' _cell_length_a 7.73155(6) _cell_length_b 24.5151(2) _cell_length_c 13.61877(10) _cell_angle_alpha 90.00 _cell_angle_beta 91.9617(7) _cell_angle_gamma 90.00 _cell_volume 2579.78(4) _cell_formula_units_Z 8 _cell_measurement_reflns_used 10305 _cell_measurement_temperature 99.9(2) _cell_measurement_theta_max 75.3210 _cell_measurement_theta_min 4.8410 _exptl_absorpt_coefficient_mu 0.826 _exptl_absorpt_correction_T_max 1.00000 _exptl_absorpt_correction_T_min 0.56906 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details ; CrysAlisPro, Agilent Technologies, Version 1.171.36.32 (release 02-08-2013 CrysAlis171 .NET) (compiled Aug 2 2013,16:46:58) Empirical absorption correction using spherical harmonics, implemented in SCALE3 ABSPACK scaling algorithm. ; _exptl_crystal_colour colourless _exptl_crystal_density_diffrn 1.402 _exptl_crystal_density_meas ? _exptl_crystal_density_method 'not measured' _exptl_crystal_description block _exptl_crystal_F_000 1152 _exptl_crystal_size_max 0.35 _exptl_crystal_size_mid 0.25 _exptl_crystal_size_min 0.25 _exptl_special_details ; ? ; _diffrn_reflns_av_R_equivalents 0.0265 _diffrn_reflns_av_unetI/netI 0.0232 _diffrn_reflns_limit_h_max 9 _diffrn_reflns_limit_h_min -9 _diffrn_reflns_limit_k_max 29 _diffrn_reflns_limit_k_min -17 _diffrn_reflns_limit_l_max 16 _diffrn_reflns_limit_l_min -16 _diffrn_reflns_number 13779 _diffrn_reflns_theta_full 66.50 _diffrn_reflns_theta_max 67.50 _diffrn_reflns_theta_min 4.86 _diffrn_ambient_temperature 99.9(2) _diffrn_detector_area_resol_mean 10.3587 _diffrn_measured_fraction_theta_full 0.9975 _diffrn_measured_fraction_theta_max 0.9805 _diffrn_measurement_details ; #__ type_ start__ end____ width___ exp.time_ 1 omega 70.00 132.00 1.0000 4.0000 omega____ theta____ kappa____ phi______ frames - 110.5703 -77.0000 -180.0000 62 #__ type_ start__ end____ width___ exp.time_ 2 omega -49.00 -10.00 1.0000 2.0000 omega____ theta____ kappa____ phi______ frames - -40.9453 37.0000 -90.0000 39 #__ type_ start__ end____ width___ exp.time_ 3 omega 10.00 35.00 1.0000 2.0000 omega____ theta____ kappa____ phi______ frames - -40.9453 37.0000 -90.0000 25 #__ type_ start__ end____ width___ exp.time_ 4 omega -112.00 -13.00 1.0000 2.0000 omega____ theta____ kappa____ phi______ frames - -40.9453 -57.0000 -90.0000 99 #__ type_ start__ end____ width___ exp.time_ 5 omega -48.00 34.00 1.0000 2.0000 omega____ theta____ kappa____ phi______ frames - -40.9453 37.0000 60.0000 82 #__ type_ start__ end____ width___ exp.time_ 6 omega -96.00 -2.00 1.0000 2.0000 omega____ theta____ kappa____ phi______ frames - -40.9453 125.0000 90.0000 94 #__ type_ start__ end____ width___ exp.time_ 7 omega 66.00 140.00 1.0000 4.0000 omega____ theta____ kappa____ phi______ frames - 110.5703 -61.0000 90.0000 74 #__ type_ start__ end____ width___ exp.time_ 8 omega 39.00 115.00 1.0000 4.0000 omega____ theta____ kappa____ phi______ frames - 110.5703 -111.0000 150.0000 76 #__ type_ start__ end____ width___ exp.time_ 9 omega 33.00 114.00 1.0000 4.0000 omega____ theta____ kappa____ phi______ frames - 110.5703 -111.0000 0.0000 81 #__ type_ start__ end____ width___ exp.time_ 10 omega 34.00 75.00 1.0000 4.0000 omega____ theta____ kappa____ phi______ frames - 110.5703 -30.0000 0.0000 41 #__ type_ start__ end____ width___ exp.time_ 11 omega 82.00 178.00 1.0000 4.0000 omega____ theta____ kappa____ phi______ frames - 110.5703 30.0000 -90.0000 96 #__ type_ start__ end____ width___ exp.time_ 12 omega 81.00 177.00 1.0000 4.0000 omega____ theta____ kappa____ phi______ frames - 110.5703 30.0000 -180.0000 96 #__ type_ start__ end____ width___ exp.time_ 13 omega 33.00 90.00 1.0000 4.0000 omega____ theta____ kappa____ phi______ frames - 110.5703 -30.0000 -120.0000 57 #__ type_ start__ end____ width___ exp.time_ 14 omega 36.00 124.00 1.0000 4.0000 omega____ theta____ kappa____ phi______ frames - 110.5703 -61.0000 -30.0000 88 ; _diffrn_measurement_device 'kappa diffractometer' _diffrn_measurement_device_type 'SuperNova, Dual, Cu at zero, Atlas' _diffrn_measurement_method '\w scans' _diffrn_orient_matrix_UB_11 0.1379696000 _diffrn_orient_matrix_UB_12 0.0269255000 _diffrn_orient_matrix_UB_13 0.0684239000 _diffrn_orient_matrix_UB_21 0.0636763000 _diffrn_orient_matrix_UB_22 0.0339628000 _diffrn_orient_matrix_UB_23 -0.0868438000 _diffrn_orient_matrix_UB_31 -0.1290244000 _diffrn_orient_matrix_UB_32 0.0455173000 _diffrn_orient_matrix_UB_33 0.0242654000 _diffrn_radiation_monochromator mirror _diffrn_radiation_probe x-ray _diffrn_radiation_type CuK\a _diffrn_radiation_wavelength 1.5418 _diffrn_source 'sealed X-ray tube' _diffrn_source_current 0.80 _diffrn_source_power 0.040 _diffrn_source_target Cu _diffrn_source_voltage 50 _diffrn_standards_decay_% ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_number ? _reflns_number_gt 4232 _reflns_number_total 4542 _reflns_odcompleteness_completeness 99.75 _reflns_odcompleteness_iscentric 1 _reflns_odcompleteness_theta 68.13 _reflns_threshold_expression >2sigma(I) _computing_cell_refinement ; CrysAlisPro, Agilent Technologies, Version 1.171.36.32 (release 02-08-2013 CrysAlis171 .NET) (compiled Aug 2 2013,16:46:58) ; _computing_data_collection ; CrysAlisPro, Agilent Technologies, Version 1.171.36.32 (release 02-08-2013 CrysAlis171 .NET) (compiled Aug 2 2013,16:46:58) ; _computing_data_reduction ; CrysAlisPro, Agilent Technologies, Version 1.171.36.32 (release 02-08-2013 CrysAlis171 .NET) (compiled Aug 2 2013,16:46:58) ; _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 ; XL, G.M. Sheldrick, Acta Cryst. (2008). A64, 112-122 ; _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _refine_diff_density_max 0.384 _refine_diff_density_min -0.193 _refine_diff_density_rms 0.037 _refine_ls_extinction_coef ? _refine_ls_extinction_method none _refine_ls_goodness_of_fit_ref 1.003 _refine_ls_hydrogen_treatment constr _refine_ls_matrix_type full _refine_ls_number_parameters 361 _refine_ls_number_reflns 4542 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0357 _refine_ls_R_factor_gt 0.0335 _refine_ls_restrained_S_all 1.003 _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^)+(0.0409P)^2^+0.9341P] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_gt 0.0812 _refine_ls_wR_factor_ref 0.0830 _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. ; _atom_sites_solution_hydrogens geom _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap 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 0.75558(13) 0.47826(4) 0.63329(6) 0.0266(2) Uani 1 1 d . . . O2 O 0.68334(12) 0.39674(3) 0.57679(6) 0.0208(2) Uani 1 1 d . . . O3 O 0.71232(11) 0.44929(3) 0.28984(6) 0.01647(18) Uani 1 1 d . . . O4 O 0.78181(12) 0.51115(3) 0.17288(6) 0.02067(19) Uani 1 1 d . . . C1 C 0.72607(16) 0.45074(5) 0.56080(9) 0.0194(3) Uani 1 1 d . . . C2 C 0.73037(15) 0.47010(5) 0.46087(9) 0.0171(2) Uani 1 1 d . . . C3 C 0.70511(15) 0.43468(5) 0.38505(8) 0.0160(2) Uani 1 1 d . . . C4 C 0.67006(15) 0.37764(5) 0.40241(9) 0.0161(2) Uani 1 1 d . . . C5 C 0.65394(15) 0.33815(5) 0.32781(9) 0.0176(2) Uani 1 1 d . . . H5 H 0.6641 0.3485 0.2611 0.021 Uiso 1 1 calc R . . C6 C 0.62336(16) 0.28422(5) 0.35130(9) 0.0192(3) Uani 1 1 d . . . H6 H 0.6129 0.2576 0.3008 0.023 Uiso 1 1 calc R . . C7 C 0.60790(16) 0.26891(5) 0.44960(10) 0.0207(3) Uani 1 1 d . . . H7 H 0.5847 0.2319 0.4652 0.025 Uiso 1 1 calc R . . C8 C 0.62596(16) 0.30701(5) 0.52440(9) 0.0209(3) Uani 1 1 d . . . H8 H 0.6165 0.2965 0.5911 0.025 Uiso 1 1 calc R . . C9 C 0.65812(15) 0.36077(5) 0.49966(9) 0.0180(2) Uani 1 1 d . . . C10 C 0.76025(16) 0.52992(5) 0.44441(9) 0.0189(3) Uani 1 1 d . . . H10A H 0.8836 0.5387 0.4584 0.023 Uiso 1 1 calc R . . H10B H 0.6898 0.5514 0.4898 0.023 Uiso 1 1 calc R . . C11 C 0.71107(17) 0.54525(5) 0.33835(9) 0.0208(3) Uani 1 1 d . . . H11 H 0.5824 0.5429 0.3290 0.025 Uiso 1 1 calc R . . C12 C 0.79336(17) 0.50299(5) 0.27312(9) 0.0199(3) Uani 1 1 d . . . H12 H 0.9187 0.5002 0.2931 0.024 Uiso 1 1 calc R . . C13 C 0.76908(19) 0.60324(5) 0.31289(9) 0.0239(3) Uani 1 1 d . . . H13A H 0.7647 0.6263 0.3724 0.029 Uiso 1 1 calc R . . H13B H 0.8906 0.6022 0.2923 0.029 Uiso 1 1 calc R . . C14 C 0.65672(19) 0.62885(5) 0.23124(10) 0.0247(3) Uani 1 1 d . . . H14A H 0.6910 0.6675 0.2242 0.030 Uiso 1 1 calc R . . H14B H 0.5348 0.6283 0.2513 0.030 Uiso 1 1 calc R . . C15 C 0.66679(18) 0.60114(5) 0.13118(9) 0.0229(3) Uani 1 1 d . . . H15A H 0.5813 0.6185 0.0853 0.027 Uiso 1 1 calc R . . H15B H 0.7831 0.6077 0.1054 0.027 Uiso 1 1 calc R . . C16 C 0.63369(17) 0.54006(5) 0.13167(9) 0.0227(3) Uani 1 1 d . . . H16A H 0.5311 0.5321 0.1708 0.027 Uiso 1 1 calc R . . H16B H 0.6090 0.5273 0.0636 0.027 Uiso 1 1 calc R . . O1A O 0.12478(14) 0.27167(4) 0.62377(6) 0.0276(2) Uani 1 1 d . . . O2A O 0.20223(12) 0.18970(3) 0.57483(6) 0.0212(2) Uani 1 1 d . . . O3A O 0.19122(11) 0.23847(3) 0.28407(6) 0.01761(19) Uani 1 1 d . . . O4A O 0.13059(11) 0.29917(3) 0.15987(6) 0.01771(18) Uani 1 1 d . . . C1A C 0.15713(16) 0.24324(5) 0.55423(9) 0.0196(3) Uani 1 1 d . . . C2A C 0.15049(15) 0.26074(5) 0.45257(9) 0.0176(2) Uani 1 1 d . . . C3A C 0.19458(15) 0.22551(5) 0.38047(9) 0.0164(2) Uani 1 1 d . . . C4A C 0.24906(15) 0.17030(5) 0.40367(9) 0.0176(2) Uani 1 1 d . . . C5A C 0.29550(16) 0.13205(5) 0.33259(9) 0.0201(3) Uani 1 1 d . . . H5A H 0.2987 0.1424 0.2655 0.024 Uiso 1 1 calc R . . C6A C 0.33656(17) 0.07925(5) 0.36053(10) 0.0228(3) Uani 1 1 d . . . H6A H 0.3679 0.0533 0.3124 0.027 Uiso 1 1 calc R . . C7A C 0.33212(17) 0.06390(5) 0.45909(10) 0.0235(3) Uani 1 1 d . . . H7A H 0.3599 0.0275 0.4774 0.028 Uiso 1 1 calc R . . C8A C 0.28762(16) 0.10115(5) 0.53057(10) 0.0221(3) Uani 1 1 d . . . H8A H 0.2847 0.0907 0.5977 0.026 Uiso 1 1 calc R . . C9A C 0.24747(16) 0.15417(5) 0.50164(9) 0.0187(3) Uani 1 1 d . . . C10A C 0.10613(17) 0.31925(5) 0.43085(9) 0.0194(3) Uani 1 1 d . . . H10C H 0.1616 0.3432 0.4813 0.023 Uiso 1 1 calc R . . H10D H -0.0207 0.3245 0.4325 0.023 Uiso 1 1 calc R . . C11A C 0.16967(16) 0.33433(5) 0.32937(8) 0.0174(2) Uani 1 1 d . . . H11A H 0.2990 0.3329 0.3324 0.021 Uiso 1 1 calc R . . C12A C 0.10521(16) 0.29038(5) 0.25845(8) 0.0168(2) Uani 1 1 d . . . H12A H -0.0218 0.2856 0.2673 0.020 Uiso 1 1 calc R . . C13A C 0.11567(16) 0.39133(5) 0.29394(9) 0.0186(2) Uani 1 1 d . . . H13C H 0.0019 0.3890 0.2585 0.022 Uiso 1 1 calc R . . H13D H 0.1025 0.4154 0.3516 0.022 Uiso 1 1 calc R . . C14A C 0.24766(17) 0.41648(5) 0.22595(9) 0.0203(3) Uani 1 1 d . . . H14C H 0.2137 0.4547 0.2123 0.024 Uiso 1 1 calc R . . H14D H 0.3619 0.4172 0.2610 0.024 Uiso 1 1 calc R . . C15A C 0.26698(17) 0.38695(5) 0.12796(9) 0.0209(3) Uani 1 1 d . . . H15C H 0.1631 0.3947 0.0857 0.025 Uiso 1 1 calc R . . H15D H 0.3679 0.4025 0.0950 0.025 Uiso 1 1 calc R . . C16A C 0.29022(16) 0.32535(5) 0.13419(9) 0.0190(3) Uani 1 1 d . . . H16C H 0.3273 0.3113 0.0701 0.023 Uiso 1 1 calc R . . H16D H 0.3818 0.3166 0.1843 0.023 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 0.0430(6) 0.0230(5) 0.0136(4) -0.0024(3) 0.0003(4) -0.0034(4) O2 0.0307(5) 0.0183(4) 0.0135(4) 0.0006(3) 0.0028(3) -0.0012(4) O3 0.0227(4) 0.0151(4) 0.0117(4) 0.0004(3) 0.0009(3) -0.0007(3) O4 0.0290(5) 0.0186(4) 0.0145(4) 0.0016(3) 0.0023(3) 0.0042(3) C1 0.0208(6) 0.0192(6) 0.0182(6) 0.0006(5) 0.0017(5) 0.0004(5) C2 0.0179(6) 0.0181(6) 0.0154(6) 0.0004(4) 0.0009(4) 0.0004(5) C3 0.0127(5) 0.0203(6) 0.0150(5) 0.0008(5) 0.0010(4) 0.0015(4) C4 0.0132(5) 0.0190(6) 0.0161(6) 0.0011(4) 0.0008(4) 0.0014(4) C5 0.0159(6) 0.0202(6) 0.0167(6) -0.0001(4) -0.0008(4) 0.0014(5) C6 0.0178(6) 0.0185(6) 0.0211(6) -0.0017(5) -0.0022(5) 0.0006(5) C7 0.0189(6) 0.0172(6) 0.0259(6) 0.0035(5) -0.0027(5) -0.0001(5) C8 0.0226(6) 0.0218(6) 0.0184(6) 0.0047(5) 0.0017(5) -0.0002(5) C9 0.0165(6) 0.0205(6) 0.0171(6) -0.0014(5) 0.0011(5) 0.0010(5) C10 0.0236(6) 0.0176(6) 0.0156(6) -0.0010(4) 0.0001(5) -0.0008(5) C11 0.0252(6) 0.0197(6) 0.0174(6) -0.0007(5) -0.0005(5) 0.0001(5) C12 0.0255(6) 0.0170(6) 0.0173(6) 0.0006(5) 0.0010(5) -0.0018(5) C13 0.0368(7) 0.0172(6) 0.0175(6) -0.0007(5) -0.0021(5) -0.0028(5) C14 0.0331(7) 0.0180(6) 0.0229(6) -0.0005(5) 0.0013(6) 0.0026(5) C15 0.0283(7) 0.0235(6) 0.0168(6) 0.0036(5) -0.0002(5) 0.0061(5) C16 0.0248(7) 0.0256(7) 0.0175(6) -0.0028(5) -0.0026(5) 0.0024(5) O1A 0.0454(6) 0.0217(5) 0.0159(4) -0.0019(4) 0.0058(4) -0.0040(4) O2A 0.0274(5) 0.0199(4) 0.0162(4) 0.0012(3) 0.0012(4) -0.0013(3) O3A 0.0240(4) 0.0151(4) 0.0138(4) 0.0001(3) 0.0017(3) 0.0022(3) O4A 0.0211(4) 0.0186(4) 0.0134(4) -0.0003(3) -0.0002(3) -0.0006(3) C1A 0.0220(6) 0.0185(6) 0.0183(6) 0.0007(5) 0.0006(5) -0.0047(5) C2A 0.0173(6) 0.0187(6) 0.0169(6) -0.0004(5) 0.0011(5) -0.0022(5) C3A 0.0143(6) 0.0192(6) 0.0157(6) 0.0015(5) -0.0003(4) -0.0023(4) C4A 0.0149(6) 0.0180(6) 0.0198(6) 0.0009(5) 0.0005(5) -0.0017(4) C5A 0.0199(6) 0.0202(6) 0.0201(6) 0.0002(5) 0.0013(5) -0.0001(5) C6A 0.0216(6) 0.0190(6) 0.0278(7) -0.0011(5) 0.0014(5) 0.0010(5) C7A 0.0203(6) 0.0183(6) 0.0316(7) 0.0040(5) -0.0016(5) 0.0013(5) C8A 0.0212(6) 0.0227(6) 0.0220(6) 0.0060(5) -0.0024(5) -0.0018(5) C9A 0.0163(6) 0.0202(6) 0.0195(6) -0.0004(5) 0.0001(5) -0.0024(5) C10A 0.0252(6) 0.0184(6) 0.0146(6) -0.0014(5) 0.0024(5) 0.0012(5) C11A 0.0198(6) 0.0176(6) 0.0148(6) -0.0012(4) 0.0011(5) 0.0012(5) C12A 0.0187(6) 0.0164(6) 0.0154(6) 0.0006(4) 0.0012(5) 0.0029(5) C13A 0.0236(6) 0.0167(6) 0.0155(5) -0.0018(4) 0.0010(5) 0.0034(5) C14A 0.0263(7) 0.0157(6) 0.0188(6) 0.0000(5) 0.0004(5) 0.0002(5) C15A 0.0247(6) 0.0210(6) 0.0170(6) 0.0022(5) 0.0019(5) -0.0009(5) C16A 0.0200(6) 0.0219(6) 0.0152(5) -0.0006(5) 0.0026(5) 0.0008(5) _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 C1 1.2110(15) . ? O2 C1 1.3833(15) . ? O2 C9 1.3803(15) . ? O3 C3 1.3482(14) . ? O3 C12 1.4790(14) . ? O4 C12 1.3795(15) . ? O4 C16 1.4439(15) . ? C1 C2 1.4428(17) . ? C2 C3 1.3580(17) . ? C2 C10 1.5028(16) . ? C3 C4 1.4454(16) . ? C4 C5 1.4058(17) . ? C4 C9 1.3935(17) . ? C5 C6 1.3824(17) . ? C6 C7 1.3994(18) . ? C7 C8 1.3855(18) . ? C8 C9 1.3850(18) . ? C10 C11 1.5280(16) . ? C11 C12 1.5186(17) . ? C11 C13 1.5339(17) . ? C13 C14 1.5228(18) . ? C14 C15 1.5270(17) . ? C15 C16 1.5192(18) . ? O1A C1A 1.2089(16) . ? O2A C1A 1.3844(15) . ? O2A C9A 1.3778(15) . ? O3A C3A 1.3501(14) . ? O3A C12A 1.4721(14) . ? O4A C12A 1.3803(14) . ? O4A C16A 1.4448(15) . ? C1A C2A 1.4486(17) . ? C2A C3A 1.3600(17) . ? C2A C10A 1.5017(16) . ? C3A C4A 1.4491(17) . ? C4A C5A 1.4033(17) . ? C4A C9A 1.3921(17) . ? C5A C6A 1.3830(18) . ? C6A C7A 1.3955(19) . ? C7A C8A 1.3867(19) . ? C8A C9A 1.3901(18) . ? C10A C11A 1.5280(16) . ? C11A C12A 1.5196(16) . ? C11A C13A 1.5316(16) . ? C13A C14A 1.5309(17) . ? C14A C15A 1.5300(16) . ? C15A C16A 1.5228(17) . ? 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 C9 O2 C1 121.32(9) . . ? C3 O3 C12 114.60(9) . . ? C12 O4 C16 118.65(9) . . ? O1 C1 O2 116.37(11) . . ? O1 C1 C2 125.16(11) . . ? O2 C1 C2 118.47(10) . . ? C1 C2 C10 118.06(10) . . ? C3 C2 C1 119.97(11) . . ? C3 C2 C10 121.97(11) . . ? O3 C3 C2 123.49(11) . . ? O3 C3 C4 115.37(10) . . ? C2 C3 C4 121.14(11) . . ? C5 C4 C3 124.09(11) . . ? C9 C4 C3 117.48(11) . . ? C9 C4 C5 118.38(11) . . ? C6 C5 C4 120.20(11) . . ? C5 C6 C7 119.91(11) . . ? C8 C7 C6 120.86(11) . . ? C9 C8 C7 118.49(11) . . ? O2 C9 C4 121.43(11) . . ? O2 C9 C8 116.40(11) . . ? C8 C9 C4 122.13(11) . . ? C2 C10 C11 110.27(10) . . ? C10 C11 C13 112.11(10) . . ? C12 C11 C10 106.83(10) . . ? C12 C11 C13 111.62(10) . . ? O3 C12 C11 109.21(10) . . ? O4 C12 O3 105.55(9) . . ? O4 C12 C11 117.76(10) . . ? C14 C13 C11 112.53(11) . . ? C13 C14 C15 115.03(11) . . ? C16 C15 C14 114.88(10) . . ? O4 C16 C15 110.74(10) . . ? C9A O2A C1A 121.41(10) . . ? C3A O3A C12A 115.31(9) . . ? C12A O4A C16A 117.12(9) . . ? O1A C1A O2A 116.45(11) . . ? O1A C1A C2A 125.20(12) . . ? O2A C1A C2A 118.36(10) . . ? C1A C2A C10A 118.13(10) . . ? C3A C2A C1A 120.03(11) . . ? C3A C2A C10A 121.70(11) . . ? O3A C3A C2A 123.76(11) . . ? O3A C3A C4A 115.32(10) . . ? C2A C3A C4A 120.92(11) . . ? C5A C4A C3A 123.58(11) . . ? C9A C4A C3A 117.54(11) . . ? C9A C4A C5A 118.83(11) . . ? C6A C5A C4A 119.83(12) . . ? C5A C6A C7A 120.26(12) . . ? C8A C7A C6A 120.83(12) . . ? C7A C8A C9A 118.37(12) . . ? O2A C9A C4A 121.64(11) . . ? O2A C9A C8A 116.47(11) . . ? C8A C9A C4A 121.87(12) . . ? C2A C10A C11A 109.33(10) . . ? C10A C11A C13A 114.40(10) . . ? C12A C11A C10A 107.13(10) . . ? C12A C11A C13A 111.52(10) . . ? O3A C12A C11A 109.06(9) . . ? O4A C12A O3A 106.70(9) . . ? O4A C12A C11A 116.94(10) . . ? C14A C13A C11A 112.19(10) . . ? C15A C14A C13A 115.10(10) . . ? C16A C15A C14A 115.81(10) . . ? O4A C16A C15A 110.73(10) . . ? 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 O1 C1 C2 C3 176.05(13) . . . . ? O1 C1 C2 C10 -4.96(19) . . . . ? O2 C1 C2 C3 -4.69(18) . . . . ? O2 C1 C2 C10 174.30(11) . . . . ? O3 C3 C4 C5 3.67(17) . . . . ? O3 C3 C4 C9 -178.82(10) . . . . ? C1 O2 C9 C4 -1.74(17) . . . . ? C1 O2 C9 C8 176.28(11) . . . . ? C1 C2 C3 O3 -177.94(11) . . . . ? C1 C2 C3 C4 1.32(18) . . . . ? C1 C2 C10 C11 -164.23(11) . . . . ? C2 C3 C4 C5 -175.65(12) . . . . ? C2 C3 C4 C9 1.86(17) . . . . ? C2 C10 C11 C12 -47.26(14) . . . . ? C2 C10 C11 C13 -169.84(10) . . . . ? C3 O3 C12 O4 -177.64(9) . . . . ? C3 O3 C12 C11 -50.14(13) . . . . ? C3 C2 C10 C11 14.74(17) . . . . ? C3 C4 C5 C6 178.83(11) . . . . ? C3 C4 C9 O2 -1.71(17) . . . . ? C3 C4 C9 C8 -179.62(11) . . . . ? C4 C5 C6 C7 0.18(18) . . . . ? C5 C4 C9 O2 175.95(11) . . . . ? C5 C4 C9 C8 -1.96(18) . . . . ? C5 C6 C7 C8 -1.18(19) . . . . ? C6 C7 C8 C9 0.59(19) . . . . ? C7 C8 C9 O2 -177.01(11) . . . . ? C7 C8 C9 C4 1.00(19) . . . . ? C9 O2 C1 O1 -175.75(11) . . . . ? C9 O2 C1 C2 4.92(17) . . . . ? C9 C4 C5 C6 1.34(17) . . . . ? C10 C2 C3 O3 3.11(19) . . . . ? C10 C2 C3 C4 -177.63(11) . . . . ? C10 C11 C12 O3 66.06(12) . . . . ? C10 C11 C12 O4 -173.66(10) . . . . ? C10 C11 C13 C14 -153.33(11) . . . . ? C11 C13 C14 C15 -65.40(15) . . . . ? C12 O3 C3 C2 15.03(16) . . . . ? C12 O3 C3 C4 -164.28(10) . . . . ? C12 O4 C16 C15 88.06(13) . . . . ? C12 C11 C13 C14 86.85(14) . . . . ? C13 C11 C12 O3 -171.06(10) . . . . ? C13 C11 C12 O4 -50.78(15) . . . . ? C13 C14 C15 C16 52.92(16) . . . . ? C14 C15 C16 O4 -75.42(14) . . . . ? C16 O4 C12 O3 92.29(11) . . . . ? C16 O4 C12 C11 -29.88(16) . . . . ? O1A C1A C2A C3A 178.09(12) . . . . ? O1A C1A C2A C10A 2.26(19) . . . . ? O2A C1A C2A C3A -2.57(18) . . . . ? O2A C1A C2A C10A -178.40(10) . . . . ? O3A C3A C4A C5A -0.13(17) . . . . ? O3A C3A C4A C9A -177.26(10) . . . . ? C1A O2A C9A C4A -0.35(17) . . . . ? C1A O2A C9A C8A -178.98(11) . . . . ? C1A C2A C3A O3A 179.71(11) . . . . ? C1A C2A C3A C4A -0.18(18) . . . . ? C1A C2A C10A C11A 159.23(11) . . . . ? C2A C3A C4A C5A 179.76(12) . . . . ? C2A C3A C4A C9A 2.64(17) . . . . ? C2A C10A C11A C12A 49.82(13) . . . . ? C2A C10A C11A C13A 173.97(10) . . . . ? C3A O3A C12A O4A 173.90(9) . . . . ? C3A O3A C12A C11A 46.73(13) . . . . ? C3A C2A C10A C11A -16.53(16) . . . . ? C3A C4A C5A C6A -176.33(12) . . . . ? C3A C4A C9A O2A -2.40(17) . . . . ? C3A C4A C9A C8A 176.16(11) . . . . ? C4A C5A C6A C7A -0.05(19) . . . . ? C5A C4A C9A O2A -179.67(11) . . . . ? C5A C4A C9A C8A -1.11(18) . . . . ? C5A C6A C7A C8A -0.4(2) . . . . ? C6A C7A C8A C9A 0.02(19) . . . . ? C7A C8A C9A O2A 179.34(11) . . . . ? C7A C8A C9A C4A 0.72(19) . . . . ? C9A O2A C1A O1A -177.74(11) . . . . ? C9A O2A C1A C2A 2.86(17) . . . . ? C9A C4A C5A C6A 0.76(18) . . . . ? C10A C2A C3A O3A -4.61(18) . . . . ? C10A C2A C3A C4A 175.50(11) . . . . ? C10A C11A C12A O3A -66.29(12) . . . . ? C10A C11A C12A O4A 172.61(10) . . . . ? C10A C11A C13A C14A 149.99(10) . . . . ? C11A C13A C14A C15A 65.27(14) . . . . ? C12A O3A C3A C2A -11.05(16) . . . . ? C12A O3A C3A C4A 168.84(10) . . . . ? C12A O4A C16A C15A -91.87(12) . . . . ? C12A C11A C13A C14A -88.24(12) . . . . ? C13A C11A C12A O3A 167.82(9) . . . . ? C13A C11A C12A O4A 46.72(14) . . . . ? C13A C14A C15A C16A -48.72(15) . . . . ? C14A C15A C16A O4A 71.67(13) . . . . ? C16A O4A C12A O3A -85.14(11) . . . . ? C16A O4A C12A C11A 37.20(14) . . . . ?