# Electronic Supplementary Material (ESI) for RSC Advances # This journal is © The Royal Society of Chemistry 2013 ####################################################################### # # Cambridge Crystallographic Data Centre # CCDC # ####################################################################### # # This CIF contains data from an original supplementary publication # deposited with the CCDC, and may include chemical, crystal, # experimental, refinement, atomic coordinates, # anisotropic displacement parameters and molecular geometry data, # as required by the journal to which it was submitted. # # This CIF is provided on the understanding that it is used for bona # fide research purposes only. It may contain copyright material # of the CCDC or of third parties, and may not be copied or further # disseminated in any form, whether machine-readable or not, # except for the purpose of generating routine backup copies # on your local computer system. # # For further information on the CCDC, data deposition and # data retrieval see: # www.ccdc.cam.ac.uk # # Bona fide researchers may freely download Mercury and enCIFer # from this site to visualise CIF-encoded structures and # to carry out CIF format checking respectively. # data_121227_pmg_52c _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C39 H32 O10, C H2 Cl2 ' _chemical_formula_sum 'C40 H34 Cl2 O10' _chemical_formula_weight 745.57 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' Cl Cl 0.3639 0.7018 '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 21/n' _symmetry_space_group_name_Hall '-P 2yn' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, y+1/2, -z+1/2' '-x, -y, -z' 'x-1/2, -y-1/2, z-1/2' _cell_length_a 11.5284(2) _cell_length_b 15.3983(3) _cell_length_c 20.2646(4) _cell_angle_alpha 90.00 _cell_angle_beta 91.7392(17) _cell_angle_gamma 90.00 _cell_volume 3595.67(11) _cell_formula_units_Z 4 _cell_measurement_temperature 170(2) _cell_measurement_reflns_used 8050 _cell_measurement_theta_min 3.6027 _cell_measurement_theta_max 67.5388 _exptl_crystal_description platelet _exptl_crystal_colour red _exptl_crystal_size_max 0.32 _exptl_crystal_size_mid 0.28 _exptl_crystal_size_min 0.13 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.377 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1552 _exptl_absorpt_coefficient_mu 2.129 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.5490 _exptl_absorpt_correction_T_max 0.7693 _exptl_absorpt_process_details ; CrysAlis PRO (Agilent Technologies, 2011) ; _exptl_special_details ; ? ; _diffrn_ambient_temperature 170(2) _diffrn_radiation_wavelength 1.54184 _diffrn_radiation_type CuK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Xcalibur, Atlas, Gemini ultra' _diffrn_measurement_method '\w scans' _diffrn_detector_area_resol_mean 10.3592 _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 18937 _diffrn_reflns_av_R_equivalents 0.0322 _diffrn_reflns_av_sigmaI/netI 0.0279 _diffrn_reflns_limit_h_min -13 _diffrn_reflns_limit_h_max 11 _diffrn_reflns_limit_k_min -18 _diffrn_reflns_limit_k_max 17 _diffrn_reflns_limit_l_min -24 _diffrn_reflns_limit_l_max 23 _diffrn_reflns_theta_min 3.61 _diffrn_reflns_theta_max 67.65 _reflns_number_total 6408 _reflns_number_gt 5587 _reflns_threshold_expression >2sigma(I) _computing_cell_refinement 'CrysAlis PRO (Agilent Technologies, 2011)' _computing_data_collection 'CrysAlis PRO' _computing_data_reduction 'CrysAlis PRO' _computing_molecular_graphics 'OLEX2 (Dolomanov et al., 2009)' _computing_publication_material OLEX2 _computing_structure_solution 'SHELXS-97 (Sheldrick, 2008)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 2008)' _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^)+(0.0902P)^2^+2.5668P] 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 none _refine_ls_extinction_coef ? _refine_ls_number_reflns 6408 _refine_ls_number_parameters 473 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0644 _refine_ls_R_factor_gt 0.0580 _refine_ls_wR_factor_ref 0.1695 _refine_ls_wR_factor_gt 0.1623 _refine_ls_goodness_of_fit_ref 1.074 _refine_ls_restrained_S_all 1.074 _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 Cl1 Cl 0.14297(10) 0.66197(9) 0.21224(6) 0.0935(4) Uani 1 1 d . . . Cl2 Cl -0.05375(13) 0.76929(9) 0.23988(9) 0.1161(5) Uani 1 1 d . . . O1 O 0.33748(14) 0.76274(11) 0.36455(10) 0.0427(4) Uani 1 1 d . . . O2 O -0.09041(14) 0.83317(11) 0.46786(9) 0.0410(4) Uani 1 1 d . . . O3 O 0.08058(14) 0.51314(11) 0.42754(9) 0.0404(4) Uani 1 1 d . . . O4 O -0.35073(13) 0.59745(12) 0.35562(9) 0.0405(4) Uani 1 1 d . . . O5 O -0.08604(15) 0.38506(12) 0.20538(9) 0.0431(4) Uani 1 1 d . . . O6 O -0.33167(15) 0.67042(12) 0.11297(9) 0.0429(4) Uani 1 1 d . . . O7 O 0.08637(16) 0.60336(12) 0.02924(11) 0.0514(5) Uani 1 1 d . . . O8 O -0.08997(16) 0.91796(12) 0.06089(10) 0.0491(5) Uani 1 1 d . . . O9 O 0.34049(15) 0.82768(12) 0.13136(9) 0.0424(4) Uani 1 1 d . . . O10 O 0.07534(15) 1.01985(12) 0.28248(8) 0.0438(4) Uani 1 1 d . . . C1 C 0.25919(19) 0.93233(15) 0.35073(11) 0.0328(5) Uani 1 1 d . . . H1A H 0.2366 0.9904 0.3669 0.039 Uiso 1 1 calc R . . H1B H 0.3426 0.9236 0.3618 0.039 Uiso 1 1 calc R . . C2 C 0.18839(18) 0.86317(14) 0.38447(10) 0.0284(4) Uani 1 1 d . . . C3 C 0.08059(19) 0.88213(15) 0.40991(10) 0.0304(5) Uani 1 1 d . . . H3 H 0.0499 0.9391 0.4053 0.037 Uiso 1 1 calc R . . C4 C 0.01687(18) 0.81890(15) 0.44204(10) 0.0301(5) Uani 1 1 d . . . C5 C 0.06156(18) 0.73564(14) 0.45046(10) 0.0285(5) Uani 1 1 d . . . C6 C 0.16858(19) 0.71606(15) 0.42376(11) 0.0306(5) Uani 1 1 d . . . H6 H 0.1991 0.6590 0.4283 0.037 Uiso 1 1 calc R . . C7 C 0.23111(18) 0.77854(15) 0.39075(11) 0.0306(5) Uani 1 1 d . . . C8 C -0.1379(2) 0.91713(19) 0.46105(18) 0.0561(8) Uani 1 1 d . . . H8A H -0.1435 0.9327 0.4142 0.084 Uiso 1 1 calc R . . H8B H -0.0879 0.9589 0.4847 0.084 Uiso 1 1 calc R . . H8C H -0.2155 0.9181 0.4795 0.084 Uiso 1 1 calc R . . C9 C 0.3712(2) 0.67375(18) 0.36072(17) 0.0529(7) Uani 1 1 d . . . H9A H 0.4404 0.6687 0.3341 0.079 Uiso 1 1 calc R . . H9B H 0.3078 0.6399 0.3402 0.079 Uiso 1 1 calc R . . H9C H 0.3884 0.6515 0.4053 0.079 Uiso 1 1 calc R . . C10 C -0.00447(19) 0.66621(15) 0.48690(10) 0.0311(5) Uani 1 1 d . . . H10A H 0.0510 0.6289 0.5121 0.037 Uiso 1 1 calc R . . H10B H -0.0565 0.6940 0.5187 0.037 Uiso 1 1 calc R . . C11 C -0.07504(18) 0.61142(14) 0.43916(10) 0.0276(4) Uani 1 1 d . . . C12 C -0.18335(19) 0.63109(15) 0.41891(11) 0.0306(5) Uani 1 1 d . . . H12 H -0.2183 0.6818 0.4362 0.037 Uiso 1 1 calc R . . C13 C -0.25084(18) 0.57805(14) 0.37129(10) 0.0293(5) Uani 1 1 d . . . C14 C -0.19420(18) 0.49993(14) 0.34277(10) 0.0276(4) Uani 1 1 d . . . C15 C -0.08612(19) 0.47963(14) 0.36327(11) 0.0306(5) Uani 1 1 d . . . H15 H -0.0511 0.4290 0.3459 0.037 Uiso 1 1 calc R . . C16 C -0.01915(18) 0.53242(14) 0.41155(10) 0.0293(5) Uani 1 1 d . . . C17 C -0.25998(19) 0.45128(15) 0.28904(11) 0.0315(5) Uani 1 1 d . . . H17A H -0.3443 0.4541 0.2968 0.038 Uiso 1 1 calc R . . H17B H -0.2363 0.3895 0.2895 0.038 Uiso 1 1 calc R . . C18 C -0.23471(18) 0.49135(14) 0.22250(11) 0.0284(4) Uani 1 1 d . . . C19 C -0.29657(18) 0.56362(15) 0.19951(11) 0.0309(5) Uani 1 1 d . . . H19 H -0.3566 0.5871 0.2252 0.037 Uiso 1 1 calc R . . C20 C -0.27166(18) 0.60163(15) 0.13963(11) 0.0309(5) Uani 1 1 d . . . C21 C -0.18196(18) 0.56936(15) 0.10125(11) 0.0309(5) Uani 1 1 d . . . C22 C -0.12014(19) 0.49741(15) 0.12457(11) 0.0323(5) Uani 1 1 d . . . H22 H -0.0592 0.4745 0.0993 0.039 Uiso 1 1 calc R . . C23 C -0.14625(18) 0.45862(15) 0.18414(11) 0.0311(5) Uani 1 1 d . . . C24 C -0.4303(3) 0.7010(2) 0.14630(17) 0.0597(8) Uani 1 1 d . . . H24A H -0.4674 0.7478 0.1205 0.090 Uiso 1 1 calc R . . H24B H -0.4060 0.7231 0.1899 0.090 Uiso 1 1 calc R . . H24C H -0.4855 0.6533 0.1514 0.090 Uiso 1 1 calc R . . C25 C -0.1213(3) 0.30941(19) 0.17031(17) 0.0591(8) Uani 1 1 d . . . H25A H -0.0990 0.3145 0.1242 0.089 Uiso 1 1 calc R . . H25B H -0.2057 0.3030 0.1721 0.089 Uiso 1 1 calc R . . H25C H -0.0835 0.2584 0.1904 0.089 Uiso 1 1 calc R . . C26 C -0.1588(2) 0.60888(17) 0.03446(11) 0.0363(5) Uani 1 1 d . . . H26A H -0.1206 0.5651 0.0066 0.044 Uiso 1 1 calc R . . H26B H -0.2336 0.6248 0.0124 0.044 Uiso 1 1 calc R . . C27 C -0.0829(2) 0.68834(16) 0.04019(10) 0.0325(5) Uani 1 1 d . . . C28 C -0.1238(2) 0.76856(17) 0.04845(11) 0.0370(5) Uani 1 1 d . . . H28 H -0.2053 0.7764 0.0506 0.044 Uiso 1 1 calc R . . C29 C -0.0485(2) 0.84537(16) 0.05431(11) 0.0350(5) Uani 1 1 d . . . C30 C 0.0800(2) 0.83252(15) 0.05203(10) 0.0318(5) Uani 1 1 d . . . C31 C 0.1210(2) 0.75241(16) 0.04367(11) 0.0356(5) Uani 1 1 d . . . H31 H 0.2026 0.7445 0.0420 0.043 Uiso 1 1 calc R . . C32 C 0.0451(2) 0.67549(16) 0.03684(11) 0.0356(5) Uani 1 1 d . . . C33 C 0.1551(2) 0.91175(16) 0.06329(11) 0.0353(5) Uani 1 1 d . . . H33A H 0.2289 0.9050 0.0401 0.042 Uiso 1 1 calc R . . H33B H 0.1148 0.9640 0.0456 0.042 Uiso 1 1 calc R . . C34 C 0.17918(18) 0.92194(14) 0.13641(11) 0.0291(5) Uani 1 1 d . . . C35 C 0.11166(18) 0.96784(14) 0.17652(11) 0.0298(5) Uani 1 1 d . . . H35 H 0.0454 0.9967 0.1581 0.036 Uiso 1 1 calc R . . C36 C 0.13671(18) 0.97499(14) 0.24793(11) 0.0294(5) Uani 1 1 d . . . C37 C 0.23970(18) 0.92826(14) 0.27696(11) 0.0284(4) Uani 1 1 d . . . C38 C 0.30745(19) 0.88358(15) 0.23673(12) 0.0333(5) Uani 1 1 d . . . H38 H 0.3753 0.8566 0.2549 0.040 Uiso 1 1 calc R . . C39 C 0.28139(18) 0.87442(14) 0.16571(11) 0.0313(5) Uani 1 1 d . . . C51 C 0.0103(4) 0.6690(3) 0.2526(2) 0.0822(11) Uani 1 1 d . . . H51A H -0.0428 0.6229 0.2359 0.099 Uiso 1 1 calc R . . H51B H 0.0239 0.6596 0.3006 0.099 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 Cl1 0.0920(7) 0.0989(8) 0.0905(7) 0.0004(6) 0.0145(6) 0.0142(6) Cl2 0.1054(9) 0.0802(8) 0.1626(13) -0.0086(8) 0.0047(8) 0.0266(7) O1 0.0324(8) 0.0309(9) 0.0654(11) 0.0031(8) 0.0137(8) 0.0039(7) O2 0.0340(9) 0.0385(9) 0.0513(10) 0.0066(8) 0.0120(7) 0.0082(7) O3 0.0302(8) 0.0370(9) 0.0535(10) -0.0009(8) -0.0057(7) 0.0071(7) O4 0.0274(8) 0.0427(10) 0.0512(10) -0.0026(8) -0.0020(7) 0.0080(7) O5 0.0414(9) 0.0380(10) 0.0498(10) 0.0021(8) 0.0000(8) 0.0140(7) O6 0.0403(9) 0.0418(10) 0.0466(10) 0.0144(8) 0.0040(7) 0.0098(7) O7 0.0460(10) 0.0369(10) 0.0724(13) -0.0148(9) 0.0190(9) -0.0049(8) O8 0.0459(10) 0.0376(10) 0.0635(12) 0.0010(8) -0.0022(9) 0.0042(8) O9 0.0379(9) 0.0430(10) 0.0471(10) -0.0036(8) 0.0165(7) 0.0076(7) O10 0.0442(10) 0.0471(10) 0.0402(9) -0.0028(8) 0.0069(7) 0.0176(8) C1 0.0317(11) 0.0302(11) 0.0363(12) -0.0007(9) -0.0013(9) -0.0040(9) C2 0.0306(10) 0.0281(11) 0.0263(10) -0.0012(8) -0.0026(8) -0.0015(8) C3 0.0333(11) 0.0283(11) 0.0295(10) -0.0006(8) -0.0025(9) 0.0040(9) C4 0.0276(10) 0.0338(12) 0.0288(10) -0.0007(9) -0.0005(8) 0.0029(9) C5 0.0300(11) 0.0306(11) 0.0247(10) -0.0002(8) -0.0026(8) -0.0005(9) C6 0.0309(11) 0.0275(11) 0.0332(11) 0.0001(9) -0.0006(9) 0.0029(9) C7 0.0266(10) 0.0317(11) 0.0337(11) -0.0022(9) 0.0013(8) 0.0012(9) C8 0.0365(14) 0.0420(15) 0.091(2) 0.0010(15) 0.0169(14) 0.0108(12) C9 0.0398(14) 0.0363(14) 0.084(2) 0.0013(13) 0.0195(13) 0.0088(11) C10 0.0341(11) 0.0338(12) 0.0254(10) 0.0030(9) 0.0012(8) -0.0004(9) C11 0.0306(10) 0.0283(11) 0.0243(10) 0.0056(8) 0.0063(8) 0.0006(8) C12 0.0305(11) 0.0313(11) 0.0303(10) 0.0009(9) 0.0069(8) 0.0049(9) C13 0.0275(11) 0.0298(11) 0.0308(10) 0.0054(9) 0.0050(8) 0.0032(9) C14 0.0290(10) 0.0254(10) 0.0286(10) 0.0048(8) 0.0036(8) 0.0003(8) C15 0.0320(11) 0.0253(11) 0.0346(11) 0.0014(9) 0.0039(9) 0.0049(9) C16 0.0286(11) 0.0278(11) 0.0318(11) 0.0065(9) 0.0033(8) 0.0028(8) C17 0.0307(11) 0.0282(11) 0.0355(11) 0.0015(9) 0.0012(9) -0.0020(9) C18 0.0252(10) 0.0271(11) 0.0326(11) -0.0020(9) -0.0023(8) -0.0035(8) C19 0.0271(10) 0.0302(11) 0.0354(11) -0.0005(9) 0.0011(8) 0.0004(8) C20 0.0277(10) 0.0287(11) 0.0359(11) 0.0013(9) -0.0029(9) -0.0007(9) C21 0.0298(11) 0.0322(11) 0.0305(11) -0.0027(9) -0.0030(8) -0.0076(9) C22 0.0270(10) 0.0351(12) 0.0350(11) -0.0075(9) 0.0014(9) -0.0027(9) C23 0.0284(10) 0.0289(11) 0.0357(11) -0.0027(9) -0.0035(9) 0.0015(9) C24 0.0545(17) 0.0591(19) 0.0664(19) 0.0210(15) 0.0158(14) 0.0281(15) C25 0.0691(19) 0.0336(14) 0.075(2) -0.0071(14) 0.0050(16) 0.0116(13) C26 0.0375(12) 0.0409(13) 0.0303(11) -0.0019(9) -0.0002(9) -0.0089(10) C27 0.0365(12) 0.0383(13) 0.0225(10) -0.0006(9) 0.0006(8) -0.0077(10) C28 0.0328(11) 0.0430(14) 0.0349(12) 0.0037(10) -0.0031(9) -0.0039(10) C29 0.0401(12) 0.0363(13) 0.0283(11) 0.0042(9) -0.0008(9) -0.0008(10) C30 0.0368(12) 0.0350(12) 0.0238(10) 0.0014(9) 0.0052(8) -0.0063(9) C31 0.0336(11) 0.0375(13) 0.0363(12) -0.0025(10) 0.0107(9) -0.0050(10) C32 0.0405(12) 0.0362(13) 0.0309(11) -0.0040(9) 0.0106(9) -0.0044(10) C33 0.0400(12) 0.0341(12) 0.0322(11) 0.0039(9) 0.0070(9) -0.0074(10) C34 0.0289(10) 0.0246(10) 0.0343(11) 0.0019(8) 0.0058(8) -0.0056(8) C35 0.0261(10) 0.0264(11) 0.0369(11) 0.0027(9) 0.0033(8) 0.0002(8) C36 0.0271(10) 0.0252(11) 0.0364(11) 0.0010(9) 0.0058(9) -0.0006(8) C37 0.0248(10) 0.0247(10) 0.0356(11) 0.0036(9) 0.0028(8) -0.0038(8) C38 0.0253(10) 0.0338(12) 0.0411(12) 0.0026(9) 0.0028(9) 0.0020(9) C39 0.0264(10) 0.0269(11) 0.0411(12) 0.0008(9) 0.0108(9) -0.0018(8) C51 0.092(3) 0.072(3) 0.084(3) 0.021(2) 0.003(2) -0.018(2) _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 Cl1 C51 1.760(5) . ? Cl2 C51 1.727(5) . ? O1 C7 1.373(3) . ? O1 C9 1.427(3) . ? O2 C4 1.375(3) . ? O2 C8 1.409(3) . ? O3 C16 1.222(3) . ? O4 C13 1.222(3) . ? O5 C23 1.390(3) . ? O5 C25 1.418(4) . ? O6 C20 1.367(3) . ? O6 C24 1.421(3) . ? O7 C32 1.220(3) . ? O8 C29 1.225(3) . ? O9 C39 1.223(3) . ? O10 C36 1.224(3) . ? C1 C37 1.506(3) . ? C1 C2 1.517(3) . ? C1 H1A 0.9900 . ? C1 H1B 0.9900 . ? C2 C3 1.391(3) . ? C2 C7 1.398(3) . ? C3 C4 1.393(3) . ? C3 H3 0.9500 . ? C4 C5 1.390(3) . ? C5 C6 1.395(3) . ? C5 C10 1.517(3) . ? C6 C7 1.386(3) . ? C6 H6 0.9500 . ? C8 H8A 0.9800 . ? C8 H8B 0.9800 . ? C8 H8C 0.9800 . ? C9 H9A 0.9800 . ? C9 H9B 0.9800 . ? C9 H9C 0.9800 . ? C10 C11 1.504(3) . ? C10 H10A 0.9900 . ? C10 H10B 0.9900 . ? C11 C12 1.337(3) . ? C11 C16 1.493(3) . ? C12 C13 1.469(3) . ? C12 H12 0.9500 . ? C13 C14 1.493(3) . ? C14 C15 1.338(3) . ? C14 C17 1.507(3) . ? C15 C16 1.473(3) . ? C15 H15 0.9500 . ? C17 C18 1.519(3) . ? C17 H17A 0.9900 . ? C17 H17B 0.9900 . ? C18 C19 1.394(3) . ? C18 C23 1.395(3) . ? C19 C20 1.385(3) . ? C19 H19 0.9500 . ? C20 C21 1.404(3) . ? C21 C22 1.392(3) . ? C21 C26 1.515(3) . ? C22 C23 1.388(3) . ? C22 H22 0.9500 . ? C24 H24A 0.9800 . ? C24 H24B 0.9800 . ? C24 H24C 0.9800 . ? C25 H25A 0.9800 . ? C25 H25B 0.9800 . ? C25 H25C 0.9800 . ? C26 C27 1.507(3) . ? C26 H26A 0.9900 . ? C26 H26B 0.9900 . ? C27 C28 1.335(4) . ? C27 C32 1.492(3) . ? C28 C29 1.470(3) . ? C28 H28 0.9500 . ? C29 C30 1.497(3) . ? C30 C31 1.333(3) . ? C30 C33 1.509(3) . ? C31 C32 1.477(3) . ? C31 H31 0.9500 . ? C33 C34 1.508(3) . ? C33 H33A 0.9900 . ? C33 H33B 0.9900 . ? C34 C35 1.343(3) . ? C34 C39 1.495(3) . ? C35 C36 1.471(3) . ? C35 H35 0.9500 . ? C36 C37 1.494(3) . ? C37 C38 1.337(3) . ? C38 C39 1.468(3) . ? C38 H38 0.9500 . ? C51 H51A 0.9900 . ? C51 H51B 0.9900 . ? 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 C7 O1 C9 116.04(19) . . ? C4 O2 C8 117.44(19) . . ? C23 O5 C25 112.4(2) . . ? C20 O6 C24 118.15(19) . . ? C37 C1 C2 110.60(18) . . ? C37 C1 H1A 109.5 . . ? C2 C1 H1A 109.5 . . ? C37 C1 H1B 109.5 . . ? C2 C1 H1B 109.5 . . ? H1A C1 H1B 108.1 . . ? C3 C2 C7 118.6(2) . . ? C3 C2 C1 121.2(2) . . ? C7 C2 C1 120.18(19) . . ? C2 C3 C4 121.1(2) . . ? C2 C3 H3 119.5 . . ? C4 C3 H3 119.5 . . ? O2 C4 C5 115.8(2) . . ? O2 C4 C3 124.0(2) . . ? C5 C4 C3 120.2(2) . . ? C4 C5 C6 118.7(2) . . ? C4 C5 C10 121.33(19) . . ? C6 C5 C10 119.9(2) . . ? C7 C6 C5 121.1(2) . . ? C7 C6 H6 119.5 . . ? C5 C6 H6 119.5 . . ? O1 C7 C6 123.2(2) . . ? O1 C7 C2 116.52(19) . . ? C6 C7 C2 120.3(2) . . ? O2 C8 H8A 109.5 . . ? O2 C8 H8B 109.5 . . ? H8A C8 H8B 109.5 . . ? O2 C8 H8C 109.5 . . ? H8A C8 H8C 109.5 . . ? H8B C8 H8C 109.5 . . ? O1 C9 H9A 109.5 . . ? O1 C9 H9B 109.5 . . ? H9A C9 H9B 109.5 . . ? O1 C9 H9C 109.5 . . ? H9A C9 H9C 109.5 . . ? H9B C9 H9C 109.5 . . ? C11 C10 C5 110.60(17) . . ? C11 C10 H10A 109.5 . . ? C5 C10 H10A 109.5 . . ? C11 C10 H10B 109.5 . . ? C5 C10 H10B 109.5 . . ? H10A C10 H10B 108.1 . . ? C12 C11 C16 118.6(2) . . ? C12 C11 C10 123.5(2) . . ? C16 C11 C10 117.83(19) . . ? C11 C12 C13 123.1(2) . . ? C11 C12 H12 118.4 . . ? C13 C12 H12 118.4 . . ? O4 C13 C12 120.7(2) . . ? O4 C13 C14 121.1(2) . . ? C12 C13 C14 118.23(18) . . ? C15 C14 C13 118.8(2) . . ? C15 C14 C17 123.5(2) . . ? C13 C14 C17 117.62(18) . . ? C14 C15 C16 122.8(2) . . ? C14 C15 H15 118.6 . . ? C16 C15 H15 118.6 . . ? O3 C16 C15 120.8(2) . . ? O3 C16 C11 120.8(2) . . ? C15 C16 C11 118.37(18) . . ? C14 C17 C18 109.49(17) . . ? C14 C17 H17A 109.8 . . ? C18 C17 H17A 109.8 . . ? C14 C17 H17B 109.8 . . ? C18 C17 H17B 109.8 . . ? H17A C17 H17B 108.2 . . ? C19 C18 C23 118.5(2) . . ? C19 C18 C17 120.72(19) . . ? C23 C18 C17 120.7(2) . . ? C20 C19 C18 120.8(2) . . ? C20 C19 H19 119.6 . . ? C18 C19 H19 119.6 . . ? O6 C20 C19 123.9(2) . . ? O6 C20 C21 115.3(2) . . ? C19 C20 C21 120.8(2) . . ? C22 C21 C20 118.2(2) . . ? C22 C21 C26 121.4(2) . . ? C20 C21 C26 120.4(2) . . ? C23 C22 C21 121.0(2) . . ? C23 C22 H22 119.5 . . ? C21 C22 H22 119.5 . . ? C22 C23 O5 120.0(2) . . ? C22 C23 C18 120.7(2) . . ? O5 C23 C18 119.2(2) . . ? O6 C24 H24A 109.5 . . ? O6 C24 H24B 109.5 . . ? H24A C24 H24B 109.5 . . ? O6 C24 H24C 109.5 . . ? H24A C24 H24C 109.5 . . ? H24B C24 H24C 109.5 . . ? O5 C25 H25A 109.5 . . ? O5 C25 H25B 109.5 . . ? H25A C25 H25B 109.5 . . ? O5 C25 H25C 109.5 . . ? H25A C25 H25C 109.5 . . ? H25B C25 H25C 109.5 . . ? C27 C26 C21 112.02(18) . . ? C27 C26 H26A 109.2 . . ? C21 C26 H26A 109.2 . . ? C27 C26 H26B 109.2 . . ? C21 C26 H26B 109.2 . . ? H26A C26 H26B 107.9 . . ? C28 C27 C32 118.8(2) . . ? C28 C27 C26 123.7(2) . . ? C32 C27 C26 117.5(2) . . ? C27 C28 C29 123.0(2) . . ? C27 C28 H28 118.5 . . ? C29 C28 H28 118.5 . . ? O8 C29 C28 120.8(2) . . ? O8 C29 C30 120.9(2) . . ? C28 C29 C30 118.3(2) . . ? C31 C30 C29 118.7(2) . . ? C31 C30 C33 124.3(2) . . ? C29 C30 C33 116.9(2) . . ? C30 C31 C32 122.9(2) . . ? C30 C31 H31 118.6 . . ? C32 C31 H31 118.6 . . ? O7 C32 C31 120.6(2) . . ? O7 C32 C27 121.1(2) . . ? C31 C32 C27 118.3(2) . . ? C34 C33 C30 108.69(17) . . ? C34 C33 H33A 110.0 . . ? C30 C33 H33A 110.0 . . ? C34 C33 H33B 110.0 . . ? C30 C33 H33B 110.0 . . ? H33A C33 H33B 108.3 . . ? C35 C34 C39 118.8(2) . . ? C35 C34 C33 123.8(2) . . ? C39 C34 C33 117.33(19) . . ? C34 C35 C36 122.3(2) . . ? C34 C35 H35 118.8 . . ? C36 C35 H35 118.8 . . ? O10 C36 C35 120.4(2) . . ? O10 C36 C37 120.9(2) . . ? C35 C36 C37 118.76(18) . . ? C38 C37 C36 118.7(2) . . ? C38 C37 C1 123.7(2) . . ? C36 C37 C1 117.62(19) . . ? C37 C38 C39 122.8(2) . . ? C37 C38 H38 118.6 . . ? C39 C38 H38 118.6 . . ? O9 C39 C38 120.9(2) . . ? O9 C39 C34 120.5(2) . . ? C38 C39 C34 118.54(19) . . ? Cl2 C51 Cl1 111.0(2) . . ? Cl2 C51 H51A 109.4 . . ? Cl1 C51 H51A 109.4 . . ? Cl2 C51 H51B 109.4 . . ? Cl1 C51 H51B 109.4 . . ? H51A C51 H51B 108.0 . . ? _diffrn_measured_fraction_theta_max 0.985 _diffrn_reflns_theta_full 67.65 _diffrn_measured_fraction_theta_full 0.985 _refine_diff_density_max 1.175 _refine_diff_density_min -0.885 _refine_diff_density_rms 0.060 _database_code_depnum_ccdc_archive 'CCDC 938940' ####################################################################### # # Cambridge Crystallographic Data Centre # CCDC # ####################################################################### # # This CIF contains data from an original supplementary publication # deposited with the CCDC, and may include chemical, crystal, # experimental, refinement, atomic coordinates, # anisotropic displacement parameters and molecular geometry data, # as required by the journal to which it was submitted. # # This CIF is provided on the understanding that it is used for bona # fide research purposes only. It may contain copyright material # of the CCDC or of third parties, and may not be copied or further # disseminated in any form, whether machine-readable or not, # except for the purpose of generating routine backup copies # on your local computer system. # # For further information on the CCDC, data deposition and # data retrieval see: # www.ccdc.cam.ac.uk # # Bona fide researchers may freely download Mercury and enCIFer # from this site to visualise CIF-encoded structures and # to carry out CIF format checking respectively. # data_130507_pmg_52d _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C37 H26 O10, 3(C2 H3 N)' _chemical_formula_sum 'C43 H35 N3 O10' _chemical_formula_weight 753.74 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' N N 0.0311 0.0180 '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 21/c' _symmetry_space_group_name_Hall '-P 2ybc' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y-1/2, z-1/2' _cell_length_a 12.0359(3) _cell_length_b 21.1081(5) _cell_length_c 14.8313(4) _cell_angle_alpha 90.00 _cell_angle_beta 98.540(3) _cell_angle_gamma 90.00 _cell_volume 3726.19(16) _cell_formula_units_Z 4 _cell_measurement_temperature 170(2) _cell_measurement_reflns_used 4722 _cell_measurement_theta_min 3.0105 _cell_measurement_theta_max 67.3549 _exptl_crystal_description block _exptl_crystal_colour red _exptl_crystal_size_max 0.32 _exptl_crystal_size_mid 0.26 _exptl_crystal_size_min 0.20 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.344 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1576 _exptl_absorpt_coefficient_mu 0.799 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.7840 _exptl_absorpt_correction_T_max 0.8565 _exptl_absorpt_process_details ; CrysAlis PRO (Agilent Technologies, 2011) ; _exptl_special_details ; ? ; _diffrn_ambient_temperature 170(2) _diffrn_radiation_wavelength 1.54184 _diffrn_radiation_type CuK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Xcalibur, Atlas, Gemini ultra' _diffrn_measurement_method '\w scans' _diffrn_detector_area_resol_mean 10.3592 _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 13643 _diffrn_reflns_av_R_equivalents 0.0287 _diffrn_reflns_av_sigmaI/netI 0.0346 _diffrn_reflns_limit_h_min -11 _diffrn_reflns_limit_h_max 14 _diffrn_reflns_limit_k_min -21 _diffrn_reflns_limit_k_max 25 _diffrn_reflns_limit_l_min -16 _diffrn_reflns_limit_l_max 17 _diffrn_reflns_theta_min 3.67 _diffrn_reflns_theta_max 67.47 _reflns_number_total 6549 _reflns_number_gt 5203 _reflns_threshold_expression >2sigma(I) _computing_cell_refinement 'CrysAlis PRO (Agilent Technologies, 2011)' _computing_data_collection 'CrysAlis PRO' _computing_data_reduction 'CrysAlis PRO' _computing_molecular_graphics 'OLEX2 (Dolomanov et al., 2009)' _computing_publication_material OLEX2 _computing_structure_solution 'SHELXS-97 (Sheldrick, 2008)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 2008)' _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^)+(0.1001P)^2^+1.7086P] 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 none _refine_ls_extinction_coef ? _refine_ls_number_reflns 6549 _refine_ls_number_parameters 510 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0714 _refine_ls_R_factor_gt 0.0580 _refine_ls_wR_factor_ref 0.1761 _refine_ls_wR_factor_gt 0.1618 _refine_ls_goodness_of_fit_ref 1.036 _refine_ls_restrained_S_all 1.036 _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 0.64085(15) 0.39634(8) 0.11756(11) 0.0408(4) Uani 1 1 d . . . O2 O 0.52574(15) 0.29090(9) 0.43160(11) 0.0435(4) Uani 1 1 d . . . O3 O 0.88523(16) 0.23830(9) 0.01686(13) 0.0502(5) Uani 1 1 d . . . O4 O 1.01036(18) 0.31630(10) 0.35506(13) 0.0568(5) Uani 1 1 d . . . O5 O 0.79795(19) 0.01647(11) -0.02644(15) 0.0645(6) Uani 1 1 d . . . O6 O 1.09799(16) 0.08130(11) 0.25645(14) 0.0570(5) Uani 1 1 d . . . O7 O 0.58180(16) -0.08003(9) 0.02371(12) 0.0450(4) Uani 1 1 d . . . O8 O 0.58053(16) 0.03586(10) 0.33911(13) 0.0542(5) Uani 1 1 d . . . O9 O 0.34583(16) 0.23803(8) 0.11638(12) 0.0455(4) Uani 1 1 d . . . O10 O 0.33894(15) 0.08621(8) 0.39893(12) 0.0416(4) Uani 1 1 d . . . N1 N 0.7603(4) 0.1469(2) 0.1952(3) 0.1065(13) Uani 1 1 d . . . N2 N 0.9113(4) 0.0723(3) 0.4124(3) 0.1227(16) Uani 1 1 d . . . N3 N 1.1088(3) 0.10987(18) 0.6374(2) 0.0839(9) Uani 1 1 d . . . C1 C 0.6093(2) 0.36945(10) 0.19454(15) 0.0335(5) Uani 1 1 d . . . C2 C 0.5004(2) 0.35078(10) 0.20135(16) 0.0334(5) Uani 1 1 d . . . H2 H 0.4431 0.3562 0.1505 0.040 Uiso 1 1 calc R . . C3 C 0.47377(19) 0.32444(10) 0.28090(16) 0.0335(5) Uani 1 1 d . . . C4 C 0.5579(2) 0.31784(10) 0.35563(16) 0.0341(5) Uani 1 1 d . . . C5 C 0.6674(2) 0.33669(10) 0.34882(16) 0.0337(5) Uani 1 1 d . . . H5 H 0.7241 0.3324 0.4003 0.040 Uiso 1 1 calc R . . C6 C 0.69521(19) 0.36153(10) 0.26863(16) 0.0329(5) Uani 1 1 d . . . C7 C 0.5540(3) 0.40681(15) 0.04231(18) 0.0532(7) Uani 1 1 d . . . H7A H 0.5859 0.4272 -0.0074 0.080 Uiso 1 1 calc R . . H7B H 0.4962 0.4343 0.0615 0.080 Uiso 1 1 calc R . . H7C H 0.5205 0.3662 0.0212 0.080 Uiso 1 1 calc R . . C8 C 0.5973(2) 0.29893(16) 0.51597(18) 0.0519(7) Uani 1 1 d . . . H8A H 0.6686 0.2770 0.5137 0.078 Uiso 1 1 calc R . . H8B H 0.5611 0.2811 0.5653 0.078 Uiso 1 1 calc R . . H8C H 0.6115 0.3442 0.5272 0.078 Uiso 1 1 calc R . . C9 C 0.8158(2) 0.37887(12) 0.26138(17) 0.0383(5) Uani 1 1 d . . . H9A H 0.8165 0.4171 0.2229 0.046 Uiso 1 1 calc R . . H9B H 0.8558 0.3892 0.3229 0.046 Uiso 1 1 calc R . . C10 C 0.8777(2) 0.32589(12) 0.22091(17) 0.0374(5) Uani 1 1 d . . . C11 C 0.9769(2) 0.29684(12) 0.27842(17) 0.0404(6) Uani 1 1 d . . . C12 C 1.0359(2) 0.24441(13) 0.23966(19) 0.0439(6) Uani 1 1 d . . . H12 H 1.0974 0.2250 0.2771 0.053 Uiso 1 1 calc R . . C13 C 1.00745(19) 0.22290(12) 0.15489(18) 0.0392(6) Uani 1 1 d . . . C14 C 0.9108(2) 0.25337(12) 0.09645(17) 0.0403(6) Uani 1 1 d . . . C15 C 0.8492(2) 0.30354(13) 0.13650(18) 0.0434(6) Uani 1 1 d . . . H15 H 0.7850 0.3212 0.1001 0.052 Uiso 1 1 calc R . . C16 C 1.0683(2) 0.17020(12) 0.1128(2) 0.0448(6) Uani 1 1 d . . . H16A H 1.0779 0.1823 0.0499 0.054 Uiso 1 1 calc R . . H16B H 1.1439 0.1645 0.1485 0.054 Uiso 1 1 calc R . . C17 C 1.00502(19) 0.10862(12) 0.11045(17) 0.0383(5) Uani 1 1 d . . . C18 C 1.0253(2) 0.06737(13) 0.19235(18) 0.0413(6) Uani 1 1 d . . . C19 C 0.9566(2) 0.00974(12) 0.19421(18) 0.0414(6) Uani 1 1 d . . . H19 H 0.9684 -0.0165 0.2468 0.050 Uiso 1 1 calc R . . C20 C 0.8786(2) -0.00707(11) 0.12503(17) 0.0372(5) Uani 1 1 d . . . C21 C 0.8651(2) 0.03207(13) 0.04064(18) 0.0428(6) Uani 1 1 d . . . C22 C 0.9324(2) 0.08961(13) 0.03890(18) 0.0429(6) Uani 1 1 d . . . H22 H 0.9239 0.1144 -0.0152 0.052 Uiso 1 1 calc R . . C23 C 0.8000(2) -0.06203(12) 0.1284(2) 0.0419(6) Uani 1 1 d . . . H23A H 0.8357 -0.0941 0.1721 0.050 Uiso 1 1 calc R . . H23B H 0.7846 -0.0821 0.0675 0.050 Uiso 1 1 calc R . . C24 C 0.6903(2) -0.04012(10) 0.15726(16) 0.0339(5) Uani 1 1 d . . . C25 C 0.6861(2) -0.01139(12) 0.23672(17) 0.0385(5) Uani 1 1 d . . . H25 H 0.7543 -0.0046 0.2768 0.046 Uiso 1 1 calc R . . C26 C 0.5802(2) 0.01022(11) 0.26504(16) 0.0360(5) Uani 1 1 d . . . C27 C 0.47404(19) 0.00063(10) 0.20230(16) 0.0309(5) Uani 1 1 d . . . C28 C 0.4776(2) -0.02825(10) 0.12300(15) 0.0324(5) Uani 1 1 d . . . H28 H 0.4094 -0.0341 0.0825 0.039 Uiso 1 1 calc R . . C29 C 0.5830(2) -0.05155(10) 0.09549(15) 0.0323(5) Uani 1 1 d . . . C30 C 0.3672(2) 0.02351(11) 0.23361(17) 0.0354(5) Uani 1 1 d . . . H30A H 0.3021 0.0097 0.1892 0.043 Uiso 1 1 calc R . . H30B H 0.3603 0.0037 0.2931 0.043 Uiso 1 1 calc R . . C31 C 0.36373(18) 0.09459(10) 0.24336(16) 0.0314(5) Uani 1 1 d . . . C32 C 0.34997(18) 0.12070(11) 0.33452(16) 0.0320(5) Uani 1 1 d . . . C33 C 0.35012(19) 0.19010(11) 0.34566(17) 0.0358(5) Uani 1 1 d . . . H33 H 0.3481 0.2072 0.4047 0.043 Uiso 1 1 calc R . . C34 C 0.35301(17) 0.22984(10) 0.27626(16) 0.0322(5) Uani 1 1 d . . . C35 C 0.35656(18) 0.20354(11) 0.18368(16) 0.0339(5) Uani 1 1 d . . . C36 C 0.36832(19) 0.13456(11) 0.17419(16) 0.0349(5) Uani 1 1 d . . . H36 H 0.3796 0.1178 0.1168 0.042 Uiso 1 1 calc R . . C37 C 0.3559(2) 0.30104(11) 0.28638(18) 0.0375(5) Uani 1 1 d . . . H37A H 0.3339 0.3131 0.3458 0.045 Uiso 1 1 calc R . . H37B H 0.3021 0.3206 0.2373 0.045 Uiso 1 1 calc R . . C38 C 0.7341(4) 0.15964(19) 0.2582(4) 0.0818(12) Uani 1 1 d . . . C39 C 0.7074(5) 0.17227(18) 0.3495(3) 0.0937(14) Uani 1 1 d . . . H39A H 0.6364 0.1956 0.3447 0.141 Uiso 1 1 calc R . . H39B H 0.7676 0.1976 0.3837 0.141 Uiso 1 1 calc R . . H39C H 0.7005 0.1321 0.3812 0.141 Uiso 1 1 calc R . . C40 C 0.8750(3) 0.0444(2) 0.4684(3) 0.0739(10) Uani 1 1 d . . . C41 C 0.8281(4) 0.0093(2) 0.5349(3) 0.0910(13) Uani 1 1 d . . . H41A H 0.7772 -0.0230 0.5046 0.137 Uiso 1 1 calc R . . H41B H 0.7861 0.0379 0.5696 0.137 Uiso 1 1 calc R . . H41C H 0.8884 -0.0112 0.5763 0.137 Uiso 1 1 calc R . . C42 C 1.1175(3) 0.13591(17) 0.5713(3) 0.0635(8) Uani 1 1 d . . . C43 C 1.1271(4) 0.16976(19) 0.4884(3) 0.0808(11) Uani 1 1 d . . . H43A H 1.1548 0.1410 0.4448 0.121 Uiso 1 1 calc R . . H43B H 1.1797 0.2051 0.5019 0.121 Uiso 1 1 calc R . . H43C H 1.0532 0.1862 0.4620 0.121 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 0.0465(10) 0.0406(9) 0.0342(9) 0.0072(7) 0.0023(7) -0.0009(8) O2 0.0463(10) 0.0461(10) 0.0382(9) 0.0060(8) 0.0064(7) -0.0067(8) O3 0.0509(11) 0.0557(11) 0.0428(10) -0.0015(9) 0.0025(8) 0.0119(9) O4 0.0565(12) 0.0642(13) 0.0448(11) -0.0012(9) -0.0085(9) 0.0009(10) O5 0.0610(13) 0.0703(14) 0.0551(12) 0.0071(11) -0.0146(10) -0.0146(11) O6 0.0422(11) 0.0711(14) 0.0529(11) 0.0105(10) -0.0086(9) -0.0101(10) O7 0.0537(11) 0.0437(10) 0.0388(9) -0.0099(8) 0.0107(8) -0.0041(8) O8 0.0445(10) 0.0717(13) 0.0461(11) -0.0271(10) 0.0056(8) -0.0023(9) O9 0.0549(11) 0.0338(9) 0.0461(10) 0.0037(8) 0.0016(8) -0.0047(8) O10 0.0473(10) 0.0357(9) 0.0419(9) 0.0018(8) 0.0063(8) -0.0007(7) N1 0.091(3) 0.126(4) 0.102(3) 0.040(3) 0.013(2) 0.008(2) N2 0.104(3) 0.162(4) 0.103(3) 0.016(3) 0.021(3) -0.041(3) N3 0.099(3) 0.079(2) 0.072(2) -0.0009(18) 0.0076(18) 0.0222(19) C1 0.0417(13) 0.0254(11) 0.0323(11) -0.0001(9) 0.0021(9) -0.0006(9) C2 0.0343(12) 0.0244(10) 0.0391(12) -0.0033(9) -0.0024(9) 0.0002(9) C3 0.0342(12) 0.0207(10) 0.0439(13) -0.0028(9) 0.0002(10) -0.0008(9) C4 0.0404(12) 0.0238(10) 0.0376(12) -0.0008(9) 0.0042(10) -0.0012(9) C5 0.0349(12) 0.0286(11) 0.0354(12) 0.0001(9) -0.0019(9) -0.0002(9) C6 0.0341(12) 0.0255(10) 0.0378(12) -0.0026(9) 0.0010(9) -0.0031(9) C7 0.0593(17) 0.0614(18) 0.0359(14) 0.0087(12) -0.0024(12) 0.0069(14) C8 0.0505(16) 0.0666(18) 0.0378(14) 0.0106(13) 0.0039(11) 0.0043(14) C9 0.0365(13) 0.0355(12) 0.0417(13) -0.0023(10) 0.0018(10) -0.0078(10) C10 0.0304(12) 0.0379(12) 0.0433(13) 0.0035(10) 0.0033(10) -0.0059(10) C11 0.0349(12) 0.0417(13) 0.0428(14) 0.0054(11) 0.0000(10) -0.0072(10) C12 0.0321(12) 0.0436(14) 0.0532(16) 0.0091(12) -0.0034(11) -0.0018(11) C13 0.0281(11) 0.0386(13) 0.0504(14) 0.0057(11) 0.0045(10) -0.0036(10) C14 0.0342(12) 0.0436(14) 0.0418(14) 0.0033(11) 0.0016(10) 0.0000(10) C15 0.0363(13) 0.0462(14) 0.0450(14) -0.0006(12) -0.0030(10) 0.0060(11) C16 0.0301(12) 0.0430(14) 0.0614(16) 0.0055(12) 0.0071(11) 0.0005(10) C17 0.0281(11) 0.0405(13) 0.0474(14) 0.0039(11) 0.0088(10) 0.0050(10) C18 0.0291(12) 0.0478(14) 0.0466(14) 0.0038(11) 0.0039(10) 0.0044(11) C19 0.0343(13) 0.0409(13) 0.0482(14) 0.0086(11) 0.0041(11) 0.0046(10) C20 0.0313(12) 0.0346(12) 0.0471(13) 0.0005(10) 0.0102(10) 0.0074(10) C21 0.0345(12) 0.0470(14) 0.0455(14) 0.0004(12) 0.0015(11) 0.0037(11) C22 0.0386(13) 0.0458(14) 0.0431(14) 0.0080(11) 0.0018(11) 0.0039(11) C23 0.0372(13) 0.0313(12) 0.0586(16) -0.0042(11) 0.0121(11) 0.0040(10) C24 0.0347(12) 0.0239(10) 0.0434(13) 0.0015(9) 0.0075(10) 0.0007(9) C25 0.0321(12) 0.0400(13) 0.0420(13) -0.0060(10) 0.0007(10) 0.0007(10) C26 0.0359(12) 0.0330(12) 0.0388(13) -0.0055(10) 0.0050(10) -0.0006(10) C27 0.0333(12) 0.0201(10) 0.0392(12) 0.0010(9) 0.0051(9) 0.0010(8) C28 0.0361(12) 0.0237(10) 0.0354(12) 0.0004(9) -0.0012(9) 0.0001(9) C29 0.0419(13) 0.0224(10) 0.0330(12) 0.0023(9) 0.0070(9) -0.0001(9) C30 0.0325(12) 0.0258(11) 0.0478(13) -0.0043(10) 0.0054(10) -0.0007(9) C31 0.0238(10) 0.0281(11) 0.0417(12) -0.0047(9) 0.0032(9) 0.0013(9) C32 0.0253(10) 0.0309(11) 0.0394(12) 0.0003(10) 0.0029(9) -0.0003(9) C33 0.0344(12) 0.0316(12) 0.0422(13) -0.0073(10) 0.0084(10) -0.0006(9) C34 0.0223(10) 0.0278(11) 0.0460(13) -0.0041(10) 0.0030(9) -0.0006(8) C35 0.0273(11) 0.0300(11) 0.0438(13) 0.0015(10) 0.0032(9) -0.0029(9) C36 0.0338(12) 0.0317(12) 0.0396(12) -0.0054(10) 0.0062(9) 0.0006(9) C37 0.0336(12) 0.0263(11) 0.0527(14) -0.0048(10) 0.0068(10) 0.0014(9) C38 0.093(3) 0.058(2) 0.102(3) 0.004(2) 0.039(3) -0.016(2) C39 0.124(4) 0.050(2) 0.105(3) -0.015(2) 0.010(3) 0.000(2) C40 0.067(2) 0.078(2) 0.075(2) -0.002(2) 0.0076(19) -0.0008(19) C41 0.115(4) 0.074(2) 0.094(3) 0.005(2) 0.049(3) 0.019(2) C42 0.0615(19) 0.0583(19) 0.072(2) -0.0128(17) 0.0140(17) 0.0072(16) C43 0.084(3) 0.067(2) 0.101(3) -0.007(2) 0.046(2) -0.0021(19) _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 1.378(3) . ? O1 C7 1.428(3) . ? O2 C4 1.368(3) . ? O2 C8 1.420(3) . ? O3 C14 1.217(3) . ? O4 C11 1.219(3) . ? O5 C21 1.230(3) . ? O6 C18 1.228(3) . ? O7 C29 1.221(3) . ? O8 C26 1.224(3) . ? O9 C35 1.227(3) . ? O10 C32 1.224(3) . ? N1 C38 1.063(6) . ? N2 C40 1.154(6) . ? N3 C42 1.142(5) . ? C1 C2 1.387(3) . ? C1 C6 1.402(3) . ? C2 C3 1.384(3) . ? C2 H2 0.9500 . ? C3 C4 1.393(3) . ? C3 C37 1.515(3) . ? C4 C5 1.395(3) . ? C5 C6 1.386(3) . ? C5 H5 0.9500 . ? C6 C9 1.516(3) . ? C7 H7A 0.9800 . ? C7 H7B 0.9800 . ? C7 H7C 0.9800 . ? C8 H8A 0.9800 . ? C8 H8B 0.9800 . ? C8 H8C 0.9800 . ? C9 C10 1.516(4) . ? C9 H9A 0.9900 . ? C9 H9B 0.9900 . ? C10 C15 1.334(4) . ? C10 C11 1.492(3) . ? C11 C12 1.477(4) . ? C12 C13 1.333(4) . ? C12 H12 0.9500 . ? C13 C14 1.489(3) . ? C13 C16 1.517(4) . ? C14 C15 1.468(4) . ? C15 H15 0.9500 . ? C16 C17 1.504(4) . ? C16 H16A 0.9900 . ? C16 H16B 0.9900 . ? C17 C22 1.333(4) . ? C17 C18 1.485(4) . ? C18 C19 1.473(4) . ? C19 C20 1.332(4) . ? C19 H19 0.9500 . ? C20 C21 1.488(4) . ? C20 C23 1.503(4) . ? C21 C22 1.462(4) . ? C22 H22 0.9500 . ? C23 C24 1.520(3) . ? C23 H23A 0.9900 . ? C23 H23B 0.9900 . ? C24 C25 1.333(3) . ? C24 C29 1.488(3) . ? C25 C26 1.472(3) . ? C25 H25 0.9500 . ? C26 C27 1.479(3) . ? C27 C28 1.331(3) . ? C27 C30 1.510(3) . ? C28 C29 1.474(3) . ? C28 H28 0.9500 . ? C30 C31 1.508(3) . ? C30 H30A 0.9900 . ? C30 H30B 0.9900 . ? C31 C36 1.336(3) . ? C31 C32 1.492(3) . ? C32 C33 1.474(3) . ? C33 C34 1.332(3) . ? C33 H33 0.9500 . ? C34 C35 1.488(3) . ? C34 C37 1.510(3) . ? C35 C36 1.472(3) . ? C36 H36 0.9500 . ? C37 H37A 0.9900 . ? C37 H37B 0.9900 . ? C38 C39 1.462(6) . ? C39 H39A 0.9800 . ? C39 H39B 0.9800 . ? C39 H39C 0.9800 . ? C40 C41 1.416(6) . ? C41 H41A 0.9800 . ? C41 H41B 0.9800 . ? C41 H41C 0.9800 . ? C42 C43 1.441(6) . ? C43 H43A 0.9800 . ? C43 H43B 0.9800 . ? C43 H43C 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 C1 O1 C7 116.9(2) . . ? C4 O2 C8 117.9(2) . . ? O1 C1 C2 123.8(2) . . ? O1 C1 C6 115.9(2) . . ? C2 C1 C6 120.3(2) . . ? C3 C2 C1 121.1(2) . . ? C3 C2 H2 119.4 . . ? C1 C2 H2 119.4 . . ? C2 C3 C4 119.1(2) . . ? C2 C3 C37 120.9(2) . . ? C4 C3 C37 120.0(2) . . ? O2 C4 C3 115.9(2) . . ? O2 C4 C5 124.3(2) . . ? C3 C4 C5 119.8(2) . . ? C6 C5 C4 121.4(2) . . ? C6 C5 H5 119.3 . . ? C4 C5 H5 119.3 . . ? C5 C6 C1 118.3(2) . . ? C5 C6 C9 120.5(2) . . ? C1 C6 C9 121.2(2) . . ? O1 C7 H7A 109.5 . . ? O1 C7 H7B 109.5 . . ? H7A C7 H7B 109.5 . . ? O1 C7 H7C 109.5 . . ? H7A C7 H7C 109.5 . . ? H7B C7 H7C 109.5 . . ? O2 C8 H8A 109.5 . . ? O2 C8 H8B 109.5 . . ? H8A C8 H8B 109.5 . . ? O2 C8 H8C 109.5 . . ? H8A C8 H8C 109.5 . . ? H8B C8 H8C 109.5 . . ? C10 C9 C6 112.46(19) . . ? C10 C9 H9A 109.1 . . ? C6 C9 H9A 109.1 . . ? C10 C9 H9B 109.1 . . ? C6 C9 H9B 109.1 . . ? H9A C9 H9B 107.8 . . ? C15 C10 C11 117.6(2) . . ? C15 C10 C9 124.0(2) . . ? C11 C10 C9 118.4(2) . . ? O4 C11 C12 120.3(2) . . ? O4 C11 C10 121.3(2) . . ? C12 C11 C10 118.4(2) . . ? C13 C12 C11 123.5(2) . . ? C13 C12 H12 118.3 . . ? C11 C12 H12 118.3 . . ? C12 C13 C14 118.1(2) . . ? C12 C13 C16 124.5(2) . . ? C14 C13 C16 117.4(2) . . ? O3 C14 C15 120.7(2) . . ? O3 C14 C13 121.0(2) . . ? C15 C14 C13 118.3(2) . . ? C10 C15 C14 124.0(2) . . ? C10 C15 H15 118.0 . . ? C14 C15 H15 118.0 . . ? C17 C16 C13 111.7(2) . . ? C17 C16 H16A 109.3 . . ? C13 C16 H16A 109.3 . . ? C17 C16 H16B 109.3 . . ? C13 C16 H16B 109.3 . . ? H16A C16 H16B 107.9 . . ? C22 C17 C18 118.9(2) . . ? C22 C17 C16 123.3(2) . . ? C18 C17 C16 117.8(2) . . ? O6 C18 C19 121.4(2) . . ? O6 C18 C17 120.3(2) . . ? C19 C18 C17 118.3(2) . . ? C20 C19 C18 122.6(2) . . ? C20 C19 H19 118.7 . . ? C18 C19 H19 118.7 . . ? C19 C20 C21 118.5(2) . . ? C19 C20 C23 123.8(2) . . ? C21 C20 C23 117.7(2) . . ? O5 C21 C22 120.5(2) . . ? O5 C21 C20 120.6(2) . . ? C22 C21 C20 119.0(2) . . ? C17 C22 C21 122.4(2) . . ? C17 C22 H22 118.8 . . ? C21 C22 H22 118.8 . . ? C20 C23 C24 110.62(19) . . ? C20 C23 H23A 109.5 . . ? C24 C23 H23A 109.5 . . ? C20 C23 H23B 109.5 . . ? C24 C23 H23B 109.5 . . ? H23A C23 H23B 108.1 . . ? C25 C24 C29 118.4(2) . . ? C25 C24 C23 122.4(2) . . ? C29 C24 C23 119.2(2) . . ? C24 C25 C26 122.8(2) . . ? C24 C25 H25 118.6 . . ? C26 C25 H25 118.6 . . ? O8 C26 C25 120.4(2) . . ? O8 C26 C27 120.8(2) . . ? C25 C26 C27 118.8(2) . . ? C28 C27 C26 118.7(2) . . ? C28 C27 C30 124.0(2) . . ? C26 C27 C30 117.3(2) . . ? C27 C28 C29 122.6(2) . . ? C27 C28 H28 118.7 . . ? C29 C28 H28 118.7 . . ? O7 C29 C28 120.4(2) . . ? O7 C29 C24 120.9(2) . . ? C28 C29 C24 118.66(19) . . ? C31 C30 C27 112.62(19) . . ? C31 C30 H30A 109.1 . . ? C27 C30 H30A 109.1 . . ? C31 C30 H30B 109.1 . . ? C27 C30 H30B 109.1 . . ? H30A C30 H30B 107.8 . . ? C36 C31 C32 119.0(2) . . ? C36 C31 C30 123.4(2) . . ? C32 C31 C30 117.6(2) . . ? O10 C32 C33 120.1(2) . . ? O10 C32 C31 121.8(2) . . ? C33 C32 C31 118.1(2) . . ? C34 C33 C32 122.6(2) . . ? C34 C33 H33 118.7 . . ? C32 C33 H33 118.7 . . ? C33 C34 C35 119.1(2) . . ? C33 C34 C37 123.6(2) . . ? C35 C34 C37 117.4(2) . . ? O9 C35 C36 120.6(2) . . ? O9 C35 C34 121.0(2) . . ? C36 C35 C34 118.3(2) . . ? C31 C36 C35 122.4(2) . . ? C31 C36 H36 118.8 . . ? C35 C36 H36 118.8 . . ? C34 C37 C3 109.09(18) . . ? C34 C37 H37A 109.9 . . ? C3 C37 H37A 109.9 . . ? C34 C37 H37B 109.9 . . ? C3 C37 H37B 109.9 . . ? H37A C37 H37B 108.3 . . ? N1 C38 C39 173.7(6) . . ? C38 C39 H39A 109.5 . . ? C38 C39 H39B 109.5 . . ? H39A C39 H39B 109.5 . . ? C38 C39 H39C 109.5 . . ? H39A C39 H39C 109.5 . . ? H39B C39 H39C 109.5 . . ? N2 C40 C41 178.1(5) . . ? C40 C41 H41A 109.5 . . ? C40 C41 H41B 109.5 . . ? H41A C41 H41B 109.5 . . ? C40 C41 H41C 109.5 . . ? H41A C41 H41C 109.5 . . ? H41B C41 H41C 109.5 . . ? N3 C42 C43 178.9(4) . . ? C42 C43 H43A 109.5 . . ? C42 C43 H43B 109.5 . . ? H43A C43 H43B 109.5 . . ? C42 C43 H43C 109.5 . . ? H43A C43 H43C 109.5 . . ? H43B C43 H43C 109.5 . . ? _diffrn_measured_fraction_theta_max 0.975 _diffrn_reflns_theta_full 67.47 _diffrn_measured_fraction_theta_full 0.975 _refine_diff_density_max 1.158 _refine_diff_density_min -0.452 _refine_diff_density_rms 0.056 _database_code_depnum_ccdc_archive 'CCDC 938941' ####################################################################### # # Cambridge Crystallographic Data Centre # CCDC # ####################################################################### # # This CIF contains data from an original supplementary publication # deposited with the CCDC, and may include chemical, crystal, # experimental, refinement, atomic coordinates, # anisotropic displacement parameters and molecular geometry data, # as required by the journal to which it was submitted. # # This CIF is provided on the understanding that it is used for bona # fide research purposes only. It may contain copyright material # of the CCDC or of third parties, and may not be copied or further # disseminated in any form, whether machine-readable or not, # except for the purpose of generating routine backup copies # on your local computer system. # # For further information on the CCDC, data deposition and # data retrieval see: # www.ccdc.cam.ac.uk # # Bona fide researchers may freely download Mercury and enCIFer # from this site to visualise CIF-encoded structures and # to carry out CIF format checking respectively. # data_130417_pmg_71a _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C39 H38 O10, 2(C3 H6 O) ' _chemical_formula_sum 'C45 H50 O12' _chemical_formula_weight 782.85 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 Triclinic _symmetry_space_group_name_H-M 'P -1' _symmetry_space_group_name_Hall '-P 1' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 10.3617(4) _cell_length_b 12.5519(7) _cell_length_c 17.8498(9) _cell_angle_alpha 70.793(5) _cell_angle_beta 86.489(4) _cell_angle_gamma 66.809(4) _cell_volume 2008.92(17) _cell_formula_units_Z 2 _cell_measurement_temperature 170(2) _cell_measurement_reflns_used 6868 _cell_measurement_theta_min 4.0366 _cell_measurement_theta_max 67.3085 _exptl_crystal_description block _exptl_crystal_colour colorless _exptl_crystal_size_max 0.32 _exptl_crystal_size_mid 0.26 _exptl_crystal_size_min 0.23 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.294 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 832 _exptl_absorpt_coefficient_mu 0.769 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.7909 _exptl_absorpt_correction_T_max 0.8429 _exptl_absorpt_process_details ; CrysAlis PRO (Agilent Technologies, 2011) ; _exptl_special_details ; ? ; _diffrn_ambient_temperature 170(2) _diffrn_radiation_wavelength 1.54184 _diffrn_radiation_type CuK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Xcalibur, Atlas, Gemini ultra' _diffrn_measurement_method '\w scans' _diffrn_detector_area_resol_mean 10.3592 _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 15832 _diffrn_reflns_av_R_equivalents 0.0370 _diffrn_reflns_av_sigmaI/netI 0.0341 _diffrn_reflns_limit_h_min -11 _diffrn_reflns_limit_h_max 12 _diffrn_reflns_limit_k_min -14 _diffrn_reflns_limit_k_max 14 _diffrn_reflns_limit_l_min -21 _diffrn_reflns_limit_l_max 21 _diffrn_reflns_theta_min 4.04 _diffrn_reflns_theta_max 67.42 _reflns_number_total 7117 _reflns_number_gt 5944 _reflns_threshold_expression >2sigma(I) _computing_cell_refinement 'CrysAlis PRO (Agilent Technologies, 2011)' _computing_data_collection 'CrysAlis PRO' _computing_data_reduction 'CrysAlis PRO' _computing_molecular_graphics 'OLEX2 (Dolomanov et al., 2009)' _computing_publication_material OLEX2 _computing_structure_solution 'SHELXS-97 (Sheldrick, 2008)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 2008)' _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^)+(0.1213P)^2^+0.3734P] 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 none _refine_ls_extinction_coef ? _refine_ls_number_reflns 7117 _refine_ls_number_parameters 528 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0665 _refine_ls_R_factor_gt 0.0581 _refine_ls_wR_factor_ref 0.1763 _refine_ls_wR_factor_gt 0.1642 _refine_ls_goodness_of_fit_ref 1.033 _refine_ls_restrained_S_all 1.033 _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 0.05731(15) 0.06168(14) 0.72529(8) 0.0409(3) Uani 1 1 d . . . O2 O 0.11157(15) 0.10124(13) 1.02068(8) 0.0396(3) Uani 1 1 d . . . O3 O -0.39571(15) 0.63190(13) 0.74788(8) 0.0386(3) Uani 1 1 d . . . H3 H -0.3824 0.6964 0.7248 0.058 Uiso 1 1 calc R . . O4 O -0.02304(17) 0.33666(13) 1.01327(8) 0.0413(4) Uani 1 1 d . . . H4 H 0.0107 0.2627 1.0158 0.062 Uiso 1 1 calc R . . O5 O -0.34020(14) 0.83260(13) 0.66045(8) 0.0387(3) Uani 1 1 d . . . O6 O 0.19647(14) 0.76537(13) 0.74683(8) 0.0355(3) Uani 1 1 d . . . O7 O 0.05992(16) 0.71708(15) 0.49763(8) 0.0433(4) Uani 1 1 d . . . H7 H 0.0483 0.6752 0.4724 0.065 Uiso 1 1 calc R . . O8 O 0.57807(15) 0.47882(13) 0.66946(9) 0.0391(3) Uani 1 1 d . . . H8 H 0.5863 0.4088 0.6996 0.059 Uiso 1 1 calc R . . O9 O 0.2708(2) 0.07037(17) 0.62216(10) 0.0521(4) Uani 1 1 d . . . H9 H 0.2024 0.0644 0.6484 0.078 Uiso 1 1 calc R . . O10 O 0.57415(16) 0.24502(15) 0.76034(9) 0.0445(4) Uani 1 1 d . . . H10 H 0.6558 0.1908 0.7755 0.067 Uiso 1 1 calc R . . O11 O 0.0135(2) 0.3562(2) 0.61564(15) 0.0831(7) Uani 1 1 d . . . O12 O 0.4646(3) 0.1854(2) 0.99710(18) 0.1006(9) Uani 1 1 d . . . C1 C 0.0681(2) 0.07509(17) 0.79807(11) 0.0328(4) Uani 1 1 d . . . C2 C 0.2033(2) 0.02439(17) 0.83571(12) 0.0343(4) Uani 1 1 d . . . C3 C 0.2187(2) 0.03182(17) 0.91034(12) 0.0355(4) Uani 1 1 d . . . H3A H 0.3098 -0.0044 0.9373 0.043 Uiso 1 1 calc R . . C4 C 0.1023(2) 0.09166(17) 0.94592(11) 0.0320(4) Uani 1 1 d . . . C5 C -0.0315(2) 0.14680(17) 0.90717(11) 0.0301(4) Uani 1 1 d . . . C6 C -0.0474(2) 0.13600(17) 0.83363(11) 0.0312(4) Uani 1 1 d . . . H6 H -0.1388 0.1708 0.8073 0.037 Uiso 1 1 calc R . . C7 C -0.0808(2) 0.1067(2) 0.68783(13) 0.0446(5) Uani 1 1 d . . . H7A H -0.0737 0.0920 0.6368 0.067 Uiso 1 1 calc R . . H7B H -0.1284 0.1951 0.6787 0.067 Uiso 1 1 calc R . . H7C H -0.1350 0.0640 0.7223 0.067 Uiso 1 1 calc R . . C8 C 0.2447(2) 0.0379(2) 1.06590(14) 0.0433(5) Uani 1 1 d . . . H8A H 0.3109 0.0733 1.0387 0.065 Uiso 1 1 calc R . . H8B H 0.2813 -0.0493 1.0711 0.065 Uiso 1 1 calc R . . H8C H 0.2334 0.0462 1.1189 0.065 Uiso 1 1 calc R . . C9 C -0.1587(2) 0.22239(17) 0.94129(11) 0.0316(4) Uani 1 1 d . . . H9A H -0.2431 0.2129 0.9264 0.038 Uiso 1 1 calc R . . H9B H -0.1440 0.1909 1.0001 0.038 Uiso 1 1 calc R . . C10 C -0.18425(19) 0.35759(17) 0.91134(10) 0.0278(4) Uani 1 1 d . . . C11 C -0.11573(19) 0.40653(17) 0.94700(10) 0.0293(4) Uani 1 1 d . . . C12 C -0.14268(19) 0.53095(17) 0.91754(10) 0.0289(4) Uani 1 1 d . . . H12 H -0.0954 0.5623 0.9432 0.035 Uiso 1 1 calc R . . C13 C -0.23658(18) 0.61090(17) 0.85177(10) 0.0273(4) Uani 1 1 d . . . C14 C -0.30162(19) 0.56141(17) 0.81436(11) 0.0295(4) Uani 1 1 d . . . C15 C -0.27638(19) 0.43734(17) 0.84450(11) 0.0300(4) Uani 1 1 d . . . H15 H -0.3234 0.4059 0.8187 0.036 Uiso 1 1 calc R . . C16 C -0.2636(2) 0.74650(17) 0.82303(11) 0.0302(4) Uani 1 1 d . . . H16A H -0.3625 0.7951 0.8005 0.036 Uiso 1 1 calc R . . H16B H -0.2512 0.7700 0.8690 0.036 Uiso 1 1 calc R . . C17 C -0.16638(19) 0.77831(16) 0.76056(10) 0.0282(4) Uani 1 1 d . . . C18 C -0.0314(2) 0.76038(16) 0.78367(10) 0.0291(4) Uani 1 1 d . . . H18 H -0.0028 0.7324 0.8387 0.035 Uiso 1 1 calc R . . C19 C 0.06244(19) 0.78276(16) 0.72737(11) 0.0290(4) Uani 1 1 d . . . C20 C 0.0215(2) 0.82456(16) 0.64613(11) 0.0312(4) Uani 1 1 d . . . C21 C -0.1141(2) 0.84500(17) 0.62334(11) 0.0328(4) Uani 1 1 d . . . H21 H -0.1441 0.8756 0.5684 0.039 Uiso 1 1 calc R . . C22 C -0.2071(2) 0.82134(16) 0.67988(11) 0.0306(4) Uani 1 1 d . . . C23 C -0.3993(2) 0.9011(2) 0.58118(13) 0.0481(5) Uani 1 1 d . . . H23A H -0.3454 0.8579 0.5454 0.072 Uiso 1 1 calc R . . H23B H -0.3959 0.9824 0.5659 0.072 Uiso 1 1 calc R . . H23C H -0.4973 0.9105 0.5774 0.072 Uiso 1 1 calc R . . C24 C 0.2460(2) 0.7130(2) 0.82814(13) 0.0457(5) Uani 1 1 d . . . H24A H 0.3463 0.6966 0.8330 0.068 Uiso 1 1 calc R . . H24B H 0.2330 0.6358 0.8516 0.068 Uiso 1 1 calc R . . H24C H 0.1930 0.7702 0.8562 0.068 Uiso 1 1 calc R . . C25 C 0.1267(2) 0.83990(18) 0.58489(11) 0.0347(4) Uani 1 1 d . . . H25A H 0.1800 0.8819 0.5989 0.042 Uiso 1 1 calc R . . H25B H 0.0761 0.8914 0.5319 0.042 Uiso 1 1 calc R . . C26 C 0.2281(2) 0.71523(17) 0.58192(10) 0.0301(4) Uani 1 1 d . . . C27 C 0.3591(2) 0.65521(18) 0.62421(11) 0.0320(4) Uani 1 1 d . . . H27 H 0.3882 0.6953 0.6525 0.038 Uiso 1 1 calc R . . C28 C 0.4484(2) 0.53800(18) 0.62601(10) 0.0308(4) Uani 1 1 d . . . C29 C 0.4104(2) 0.47661(17) 0.58499(10) 0.0292(4) Uani 1 1 d . . . C30 C 0.2796(2) 0.53798(18) 0.54158(10) 0.0320(4) Uani 1 1 d . . . H30 H 0.2517 0.4984 0.5124 0.038 Uiso 1 1 calc R . . C31 C 0.1891(2) 0.65474(18) 0.53964(10) 0.0316(4) Uani 1 1 d . . . C32 C 0.5082(2) 0.34857(18) 0.58654(11) 0.0330(4) Uani 1 1 d . . . H32A H 0.6051 0.3328 0.6036 0.040 Uiso 1 1 calc R . . H32B H 0.5090 0.3448 0.5320 0.040 Uiso 1 1 calc R . . C33 C 0.4662(2) 0.24851(17) 0.64179(11) 0.0319(4) Uani 1 1 d . . . C34 C 0.49997(19) 0.20298(18) 0.72378(11) 0.0334(4) Uani 1 1 d . . . C35 C 0.4582(2) 0.11194(18) 0.77190(12) 0.0363(4) Uani 1 1 d . . . H35 H 0.4826 0.0812 0.8276 0.044 Uiso 1 1 calc R . . C36 C 0.3812(2) 0.06436(17) 0.74069(12) 0.0347(4) Uani 1 1 d . . . C37 C 0.3450(2) 0.11188(19) 0.65899(12) 0.0376(5) Uani 1 1 d . . . C38 C 0.3890(2) 0.20129(19) 0.61126(12) 0.0372(5) Uani 1 1 d . . . H38 H 0.3654 0.2314 0.5555 0.045 Uiso 1 1 calc R . . C39 C 0.3338(2) -0.03261(18) 0.79552(13) 0.0402(5) Uani 1 1 d . . . H39A H 0.4109 -0.0929 0.8367 0.048 Uiso 1 1 calc R . . H39B H 0.3131 -0.0771 0.7644 0.048 Uiso 1 1 calc R . . C40 C -0.1125(3) 0.5534(3) 0.62219(19) 0.0663(7) Uani 1 1 d . . . H40A H -0.0768 0.6096 0.5838 0.100 Uiso 1 1 calc R . . H40B H -0.1426 0.5815 0.6679 0.100 Uiso 1 1 calc R . . H40C H -0.1928 0.5520 0.5968 0.100 Uiso 1 1 calc R . . C41 C -0.0004(2) 0.4290(2) 0.64921(14) 0.0447(5) Uani 1 1 d . . . C42 C 0.0940(3) 0.3946(3) 0.72009(18) 0.0680(8) Uani 1 1 d . . . H42A H 0.0385 0.3985 0.7663 0.102 Uiso 1 1 calc R . . H42B H 0.1408 0.4517 0.7102 0.102 Uiso 1 1 calc R . . H42C H 0.1650 0.3108 0.7306 0.102 Uiso 1 1 calc R . . C43 C 0.2978(4) 0.3445(3) 0.8974(2) 0.0753(8) Uani 1 1 d . . . H43A H 0.2151 0.4069 0.9100 0.113 Uiso 1 1 calc R . . H43B H 0.2733 0.2782 0.8942 0.113 Uiso 1 1 calc R . . H43C H 0.3290 0.3821 0.8463 0.113 Uiso 1 1 calc R . . C44 C 0.4128(3) 0.2939(2) 0.96072(16) 0.0556(6) Uani 1 1 d . . . C45 C 0.4598(3) 0.3811(3) 0.97965(17) 0.0642(7) Uani 1 1 d . . . H45A H 0.3801 0.4407 0.9963 0.096 Uiso 1 1 calc R . . H45B H 0.4949 0.4245 0.9323 0.096 Uiso 1 1 calc R . . H45C H 0.5351 0.3353 1.0227 0.096 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 0.0450(8) 0.0412(8) 0.0398(8) -0.0203(6) 0.0169(6) -0.0167(7) O2 0.0453(8) 0.0360(8) 0.0353(7) -0.0097(6) 0.0023(6) -0.0155(6) O3 0.0391(8) 0.0347(7) 0.0410(8) -0.0094(6) -0.0067(6) -0.0150(6) O4 0.0588(9) 0.0322(7) 0.0313(7) -0.0073(6) -0.0075(6) -0.0176(7) O5 0.0353(7) 0.0405(8) 0.0342(7) -0.0082(6) -0.0036(6) -0.0113(6) O6 0.0368(7) 0.0402(8) 0.0314(7) -0.0112(6) 0.0043(5) -0.0179(6) O7 0.0445(8) 0.0514(9) 0.0334(7) -0.0176(7) -0.0022(6) -0.0149(7) O8 0.0378(8) 0.0361(8) 0.0428(8) -0.0127(6) 0.0005(6) -0.0140(6) O9 0.0715(11) 0.0670(11) 0.0532(9) -0.0397(8) 0.0340(8) -0.0513(9) O10 0.0425(8) 0.0561(10) 0.0366(8) -0.0068(7) -0.0005(6) -0.0278(7) O11 0.0815(14) 0.0679(13) 0.1019(16) -0.0565(13) -0.0291(12) -0.0035(11) O12 0.0678(14) 0.0562(13) 0.136(2) 0.0195(14) -0.0095(14) -0.0213(11) C1 0.0404(11) 0.0267(9) 0.0341(10) -0.0099(8) 0.0152(8) -0.0181(8) C2 0.0370(10) 0.0215(9) 0.0419(10) -0.0064(8) 0.0160(8) -0.0145(8) C3 0.0361(10) 0.0251(9) 0.0436(11) -0.0048(8) 0.0087(8) -0.0165(8) C4 0.0401(10) 0.0261(9) 0.0319(9) -0.0057(7) 0.0074(8) -0.0191(8) C5 0.0364(10) 0.0274(9) 0.0314(9) -0.0089(7) 0.0134(7) -0.0198(8) C6 0.0339(10) 0.0280(9) 0.0350(10) -0.0096(8) 0.0116(8) -0.0178(8) C7 0.0497(13) 0.0465(12) 0.0361(11) -0.0181(9) 0.0073(9) -0.0146(10) C8 0.0481(12) 0.0342(11) 0.0471(12) -0.0080(9) -0.0066(9) -0.0186(9) C9 0.0350(10) 0.0338(10) 0.0326(9) -0.0125(8) 0.0143(7) -0.0207(8) C10 0.0297(9) 0.0327(10) 0.0275(9) -0.0142(7) 0.0138(7) -0.0172(8) C11 0.0328(9) 0.0340(10) 0.0242(8) -0.0118(7) 0.0078(7) -0.0155(8) C12 0.0332(9) 0.0337(10) 0.0268(9) -0.0154(7) 0.0079(7) -0.0168(8) C13 0.0267(9) 0.0317(9) 0.0276(9) -0.0152(7) 0.0103(7) -0.0125(7) C14 0.0260(9) 0.0337(10) 0.0302(9) -0.0130(8) 0.0062(7) -0.0118(7) C15 0.0294(9) 0.0350(10) 0.0332(9) -0.0159(8) 0.0089(7) -0.0176(8) C16 0.0321(9) 0.0288(9) 0.0315(9) -0.0153(7) 0.0075(7) -0.0103(7) C17 0.0337(10) 0.0213(8) 0.0283(9) -0.0110(7) 0.0042(7) -0.0077(7) C18 0.0382(10) 0.0249(9) 0.0246(8) -0.0091(7) 0.0047(7) -0.0125(8) C19 0.0339(10) 0.0245(9) 0.0290(9) -0.0096(7) 0.0037(7) -0.0117(7) C20 0.0400(10) 0.0230(9) 0.0294(9) -0.0090(7) 0.0054(7) -0.0113(8) C21 0.0421(11) 0.0257(9) 0.0261(9) -0.0078(7) 0.0019(8) -0.0096(8) C22 0.0341(10) 0.0237(9) 0.0317(9) -0.0094(7) 0.0004(7) -0.0086(7) C23 0.0442(12) 0.0558(14) 0.0347(11) -0.0121(10) -0.0068(9) -0.0110(10) C24 0.0467(12) 0.0487(13) 0.0386(11) 0.0008(9) -0.0061(9) -0.0270(10) C25 0.0440(11) 0.0287(10) 0.0288(9) -0.0057(8) 0.0065(8) -0.0155(8) C26 0.0380(10) 0.0310(10) 0.0221(8) -0.0064(7) 0.0100(7) -0.0174(8) C27 0.0405(10) 0.0354(10) 0.0271(9) -0.0122(8) 0.0087(7) -0.0215(8) C28 0.0340(10) 0.0365(10) 0.0244(9) -0.0080(7) 0.0080(7) -0.0190(8) C29 0.0369(10) 0.0336(10) 0.0226(8) -0.0093(7) 0.0133(7) -0.0211(8) C30 0.0412(10) 0.0403(11) 0.0243(9) -0.0139(8) 0.0110(7) -0.0246(9) C31 0.0358(10) 0.0393(10) 0.0211(8) -0.0078(7) 0.0078(7) -0.0188(8) C32 0.0390(10) 0.0356(10) 0.0298(9) -0.0138(8) 0.0158(8) -0.0198(8) C33 0.0331(10) 0.0309(10) 0.0347(10) -0.0148(8) 0.0162(7) -0.0144(8) C34 0.0275(9) 0.0336(10) 0.0364(10) -0.0093(8) 0.0086(7) -0.0120(8) C35 0.0303(10) 0.0333(10) 0.0359(10) -0.0039(8) 0.0081(8) -0.0100(8) C36 0.0312(10) 0.0250(9) 0.0441(11) -0.0114(8) 0.0168(8) -0.0096(8) C37 0.0446(11) 0.0372(11) 0.0421(11) -0.0235(9) 0.0213(9) -0.0216(9) C38 0.0469(11) 0.0412(11) 0.0336(10) -0.0208(9) 0.0186(8) -0.0232(9) C39 0.0389(11) 0.0260(10) 0.0505(12) -0.0105(9) 0.0199(9) -0.0118(8) C40 0.0699(18) 0.0533(16) 0.0791(19) -0.0308(14) 0.0060(14) -0.0207(14) C41 0.0460(12) 0.0453(12) 0.0539(13) -0.0270(10) 0.0093(10) -0.0216(10) C42 0.0719(18) 0.0738(19) 0.0675(18) -0.0356(15) -0.0048(14) -0.0269(15) C43 0.083(2) 0.0639(19) 0.0699(19) -0.0178(15) -0.0049(16) -0.0221(16) C44 0.0418(12) 0.0497(14) 0.0599(15) -0.0053(12) 0.0158(10) -0.0149(11) C45 0.0492(14) 0.0780(19) 0.0654(17) -0.0229(14) 0.0203(12) -0.0284(14) _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 1.380(2) . ? O1 C7 1.431(3) . ? O2 C4 1.391(2) . ? O2 C8 1.428(3) . ? O3 C14 1.383(2) . ? O3 H3 0.8400 . ? O4 C11 1.373(2) . ? O4 H4 0.8400 . ? O5 C22 1.383(2) . ? O5 C23 1.417(2) . ? O6 C19 1.366(2) . ? O6 C24 1.414(3) . ? O7 C31 1.371(2) . ? O7 H7 0.8400 . ? O8 C28 1.386(2) . ? O8 H8 0.8400 . ? O9 C37 1.378(3) . ? O9 H9 0.8400 . ? O10 C34 1.379(2) . ? O10 H10 0.8400 . ? O11 C41 1.208(3) . ? O12 C44 1.204(3) . ? C1 C6 1.388(3) . ? C1 C2 1.396(3) . ? C2 C3 1.389(3) . ? C2 C39 1.520(3) . ? C3 C4 1.389(3) . ? C3 H3A 0.9500 . ? C4 C5 1.388(3) . ? C5 C6 1.389(3) . ? C5 C9 1.518(2) . ? C6 H6 0.9500 . ? C7 H7A 0.9800 . ? C7 H7B 0.9800 . ? C7 H7C 0.9800 . ? C8 H8A 0.9800 . ? C8 H8B 0.9800 . ? C8 H8C 0.9800 . ? C9 C10 1.517(3) . ? C9 H9A 0.9900 . ? C9 H9B 0.9900 . ? C10 C15 1.392(3) . ? C10 C11 1.394(3) . ? C11 C12 1.388(3) . ? C12 C13 1.389(3) . ? C12 H12 0.9500 . ? C13 C14 1.394(3) . ? C13 C16 1.519(3) . ? C14 C15 1.389(3) . ? C15 H15 0.9500 . ? C16 C17 1.518(2) . ? C16 H16A 0.9900 . ? C16 H16B 0.9900 . ? C17 C22 1.388(3) . ? C17 C18 1.392(3) . ? C18 C19 1.395(3) . ? C18 H18 0.9500 . ? C19 C20 1.399(3) . ? C20 C21 1.386(3) . ? C20 C25 1.517(3) . ? C21 C22 1.395(3) . ? C21 H21 0.9500 . ? C23 H23A 0.9800 . ? C23 H23B 0.9800 . ? C23 H23C 0.9800 . ? C24 H24A 0.9800 . ? C24 H24B 0.9800 . ? C24 H24C 0.9800 . ? C25 C26 1.519(3) . ? C25 H25A 0.9900 . ? C25 H25B 0.9900 . ? C26 C27 1.388(3) . ? C26 C31 1.402(3) . ? C27 C28 1.386(3) . ? C27 H27 0.9500 . ? C28 C29 1.390(3) . ? C29 C30 1.395(3) . ? C29 C32 1.517(3) . ? C30 C31 1.384(3) . ? C30 H30 0.9500 . ? C32 C33 1.517(2) . ? C32 H32A 0.9900 . ? C32 H32B 0.9900 . ? C33 C38 1.388(3) . ? C33 C34 1.395(3) . ? C34 C35 1.389(3) . ? C35 C36 1.397(3) . ? C35 H35 0.9500 . ? C36 C37 1.393(3) . ? C36 C39 1.520(3) . ? C37 C38 1.385(3) . ? C38 H38 0.9500 . ? C39 H39A 0.9900 . ? C39 H39B 0.9900 . ? C40 C41 1.471(4) . ? C40 H40A 0.9800 . ? C40 H40B 0.9800 . ? C40 H40C 0.9800 . ? C41 C42 1.485(4) . ? C42 H42A 0.9800 . ? C42 H42B 0.9800 . ? C42 H42C 0.9800 . ? C43 C44 1.481(4) . ? C43 H43A 0.9800 . ? C43 H43B 0.9800 . ? C43 H43C 0.9800 . ? C44 C45 1.495(4) . ? C45 H45A 0.9800 . ? C45 H45B 0.9800 . ? C45 H45C 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 C1 O1 C7 117.69(15) . . ? C4 O2 C8 118.57(16) . . ? C14 O3 H3 109.5 . . ? C11 O4 H4 109.5 . . ? C22 O5 C23 118.11(16) . . ? C19 O6 C24 118.15(15) . . ? C31 O7 H7 109.5 . . ? C28 O8 H8 109.5 . . ? C37 O9 H9 109.5 . . ? C34 O10 H10 109.5 . . ? O1 C1 C6 123.03(18) . . ? O1 C1 C2 116.79(16) . . ? C6 C1 C2 120.18(18) . . ? C3 C2 C1 118.79(17) . . ? C3 C2 C39 119.30(19) . . ? C1 C2 C39 121.83(19) . . ? C2 C3 C4 120.61(19) . . ? C2 C3 H3A 119.7 . . ? C4 C3 H3A 119.7 . . ? C5 C4 C3 120.74(18) . . ? C5 C4 O2 116.22(16) . . ? C3 C4 O2 123.04(18) . . ? C4 C5 C6 118.59(17) . . ? C4 C5 C9 121.87(17) . . ? C6 C5 C9 119.49(17) . . ? C1 C6 C5 121.00(18) . . ? C1 C6 H6 119.5 . . ? C5 C6 H6 119.5 . . ? O1 C7 H7A 109.5 . . ? O1 C7 H7B 109.5 . . ? H7A C7 H7B 109.5 . . ? O1 C7 H7C 109.5 . . ? H7A C7 H7C 109.5 . . ? H7B C7 H7C 109.5 . . ? O2 C8 H8A 109.5 . . ? O2 C8 H8B 109.5 . . ? H8A C8 H8B 109.5 . . ? O2 C8 H8C 109.5 . . ? H8A C8 H8C 109.5 . . ? H8B C8 H8C 109.5 . . ? C10 C9 C5 111.92(13) . . ? C10 C9 H9A 109.2 . . ? C5 C9 H9A 109.2 . . ? C10 C9 H9B 109.2 . . ? C5 C9 H9B 109.2 . . ? H9A C9 H9B 107.9 . . ? C15 C10 C11 117.43(17) . . ? C15 C10 C9 119.97(16) . . ? C11 C10 C9 122.58(17) . . ? O4 C11 C12 116.98(16) . . ? O4 C11 C10 122.48(17) . . ? C12 C11 C10 120.52(17) . . ? C11 C12 C13 122.02(17) . . ? C11 C12 H12 119.0 . . ? C13 C12 H12 119.0 . . ? C12 C13 C14 117.56(17) . . ? C12 C13 C16 119.69(16) . . ? C14 C13 C16 122.75(17) . . ? O3 C14 C15 116.90(16) . . ? O3 C14 C13 122.65(17) . . ? C15 C14 C13 120.43(17) . . ? C14 C15 C10 121.98(17) . . ? C14 C15 H15 119.0 . . ? C10 C15 H15 119.0 . . ? C17 C16 C13 112.88(14) . . ? C17 C16 H16A 109.0 . . ? C13 C16 H16A 109.0 . . ? C17 C16 H16B 109.0 . . ? C13 C16 H16B 109.0 . . ? H16A C16 H16B 107.8 . . ? C22 C17 C18 118.61(16) . . ? C22 C17 C16 121.35(17) . . ? C18 C17 C16 120.00(16) . . ? C17 C18 C19 121.07(17) . . ? C17 C18 H18 119.5 . . ? C19 C18 H18 119.5 . . ? O6 C19 C18 123.44(16) . . ? O6 C19 C20 116.49(16) . . ? C18 C19 C20 120.07(17) . . ? C21 C20 C19 118.67(17) . . ? C21 C20 C25 121.07(17) . . ? C19 C20 C25 120.17(17) . . ? C20 C21 C22 121.02(17) . . ? C20 C21 H21 119.5 . . ? C22 C21 H21 119.5 . . ? O5 C22 C17 116.05(16) . . ? O5 C22 C21 123.35(17) . . ? C17 C22 C21 120.52(18) . . ? O5 C23 H23A 109.5 . . ? O5 C23 H23B 109.5 . . ? H23A C23 H23B 109.5 . . ? O5 C23 H23C 109.5 . . ? H23A C23 H23C 109.5 . . ? H23B C23 H23C 109.5 . . ? O6 C24 H24A 109.5 . . ? O6 C24 H24B 109.5 . . ? H24A C24 H24B 109.5 . . ? O6 C24 H24C 109.5 . . ? H24A C24 H24C 109.5 . . ? H24B C24 H24C 109.5 . . ? C20 C25 C26 110.17(15) . . ? C20 C25 H25A 109.6 . . ? C26 C25 H25A 109.6 . . ? C20 C25 H25B 109.6 . . ? C26 C25 H25B 109.6 . . ? H25A C25 H25B 108.1 . . ? C27 C26 C31 118.05(17) . . ? C27 C26 C25 120.96(17) . . ? C31 C26 C25 120.91(18) . . ? C28 C27 C26 121.30(17) . . ? C28 C27 H27 119.3 . . ? C26 C27 H27 119.3 . . ? O8 C28 C27 120.51(17) . . ? O8 C28 C29 118.32(17) . . ? C27 C28 C29 121.17(18) . . ? C28 C29 C30 117.34(18) . . ? C28 C29 C32 121.30(18) . . ? C30 C29 C32 121.36(17) . . ? C31 C30 C29 122.06(17) . . ? C31 C30 H30 119.0 . . ? C29 C30 H30 119.0 . . ? O7 C31 C30 123.30(17) . . ? O7 C31 C26 116.64(17) . . ? C30 C31 C26 120.06(18) . . ? C29 C32 C33 113.20(14) . . ? C29 C32 H32A 108.9 . . ? C33 C32 H32A 108.9 . . ? C29 C32 H32B 108.9 . . ? C33 C32 H32B 108.9 . . ? H32A C32 H32B 107.8 . . ? C38 C33 C34 117.90(17) . . ? C38 C33 C32 119.94(17) . . ? C34 C33 C32 122.15(18) . . ? O10 C34 C35 117.49(17) . . ? O10 C34 C33 122.58(16) . . ? C35 C34 C33 119.93(19) . . ? C34 C35 C36 121.83(19) . . ? C34 C35 H35 119.1 . . ? C36 C35 H35 119.1 . . ? C37 C36 C35 118.12(17) . . ? C37 C36 C39 121.52(19) . . ? C35 C36 C39 120.31(19) . . ? O9 C37 C38 117.56(19) . . ? O9 C37 C36 122.71(17) . . ? C38 C37 C36 119.67(19) . . ? C37 C38 C33 122.51(19) . . ? C37 C38 H38 118.7 . . ? C33 C38 H38 118.7 . . ? C36 C39 C2 111.48(15) . . ? C36 C39 H39A 109.3 . . ? C2 C39 H39A 109.3 . . ? C36 C39 H39B 109.3 . . ? C2 C39 H39B 109.3 . . ? H39A C39 H39B 108.0 . . ? C41 C40 H40A 109.5 . . ? C41 C40 H40B 109.5 . . ? H40A C40 H40B 109.5 . . ? C41 C40 H40C 109.5 . . ? H40A C40 H40C 109.5 . . ? H40B C40 H40C 109.5 . . ? O11 C41 C40 121.3(2) . . ? O11 C41 C42 120.8(2) . . ? C40 C41 C42 117.9(2) . . ? C41 C42 H42A 109.5 . . ? C41 C42 H42B 109.5 . . ? H42A C42 H42B 109.5 . . ? C41 C42 H42C 109.5 . . ? H42A C42 H42C 109.5 . . ? H42B C42 H42C 109.5 . . ? C44 C43 H43A 109.5 . . ? C44 C43 H43B 109.5 . . ? H43A C43 H43B 109.5 . . ? C44 C43 H43C 109.5 . . ? H43A C43 H43C 109.5 . . ? H43B C43 H43C 109.5 . . ? O12 C44 C43 120.7(3) . . ? O12 C44 C45 121.0(3) . . ? C43 C44 C45 118.3(2) . . ? C44 C45 H45A 109.5 . . ? C44 C45 H45B 109.5 . . ? H45A C45 H45B 109.5 . . ? C44 C45 H45C 109.5 . . ? H45A C45 H45C 109.5 . . ? H45B C45 H45C 109.5 . . ? _diffrn_measured_fraction_theta_max 0.985 _diffrn_reflns_theta_full 67.42 _diffrn_measured_fraction_theta_full 0.985 _refine_diff_density_max 0.468 _refine_diff_density_min -0.472 _refine_diff_density_rms 0.065 _database_code_depnum_ccdc_archive 'CCDC 938943'