# Electronic Supplementary Material (ESI) for Chemical Communications # 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_fro6548 _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C20 H24 O6' _chemical_formula_weight 360.39 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 '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 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M P21/n 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 16.5605(3) _cell_length_b 6.61010(10) _cell_length_c 16.8166(3) _cell_angle_alpha 90.00 _cell_angle_beta 93.3030(10) _cell_angle_gamma 90.00 _cell_volume 1837.80(5) _cell_formula_units_Z 4 _cell_measurement_temperature 223(2) _cell_measurement_reflns_used 4229 _cell_measurement_theta_min 4.08 _cell_measurement_theta_max 28.28 _exptl_crystal_description block _exptl_crystal_colour colourless _exptl_crystal_size_max 0.23 _exptl_crystal_size_mid 0.15 _exptl_crystal_size_min 0.12 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.303 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 768 _exptl_absorpt_coefficient_mu 0.096 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.9783 _exptl_absorpt_correction_T_max 0.9886 _exptl_absorpt_process_details 'Denzo (Otwinowski, Borek, Majewski & Minor, 2003)' _exptl_special_details ; ? ; _diffrn_ambient_temperature 223(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'rotating anode Nonius FR591' _diffrn_radiation_monochromator 'Montel mirror' _diffrn_measurement_device_type 'Nonius KappaCCD APEXII' _diffrn_measurement_method '\w and \f scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 12943 _diffrn_reflns_av_R_equivalents 0.037 _diffrn_reflns_av_sigmaI/netI 0.0349 _diffrn_reflns_limit_h_min -21 _diffrn_reflns_limit_h_max 22 _diffrn_reflns_limit_k_min -8 _diffrn_reflns_limit_k_max 8 _diffrn_reflns_limit_l_min -22 _diffrn_reflns_limit_l_max 22 _diffrn_reflns_theta_min 4.09 _diffrn_reflns_theta_max 28.29 _reflns_number_total 4501 _reflns_number_gt 3543 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Collect (Nonius B.V., 1998)' _computing_cell_refinement 'Collect (Nonius B.V., 1998)' _computing_data_reduction 'Denzo-SMN (Otwinowski & Minor, 1997)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'XP (BrukerAXS, 2000)' _computing_publication_material 'SHELXL-97 (Sheldrick, 1997)' _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. C32-C38 refined with split positions, using AFIX 66 and SIMU. ; _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^)+(0.0305P)^2^+1.6074P] 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 4501 _refine_ls_number_parameters 279 _refine_ls_number_restraints 192 _refine_ls_R_factor_all 0.0759 _refine_ls_R_factor_gt 0.0567 _refine_ls_wR_factor_ref 0.1317 _refine_ls_wR_factor_gt 0.1184 _refine_ls_goodness_of_fit_ref 1.063 _refine_ls_restrained_S_all 1.062 _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 C1 C 0.03186(10) -0.0125(3) 0.63908(10) 0.0252(3) Uani 1 1 d . . . H1 H 0.0215 -0.0778 0.5865 0.030 Uiso 1 1 calc R . . C2 C 0.12154(10) 0.0406(3) 0.64945(10) 0.0250(3) Uani 1 1 d . . . H2 H 0.1330 0.1021 0.7026 0.030 Uiso 1 1 calc R . . C3 C 0.17137(9) -0.1529(3) 0.64279(10) 0.0240(3) Uani 1 1 d . A . H3 H 0.1604 -0.2117 0.5891 0.029 Uiso 1 1 calc R . . C4 C 0.14941(10) -0.3069(3) 0.70467(10) 0.0261(3) Uani 1 1 d . . . H4 H 0.1637 -0.2519 0.7584 0.031 Uiso 1 1 calc R . . C5 C 0.05895(10) -0.3525(3) 0.69750(10) 0.0276(4) Uani 1 1 d . . . H5 H 0.0452 -0.4477 0.7401 0.033 Uiso 1 1 calc R . . C6 C 0.00907(10) -0.1603(3) 0.70368(10) 0.0278(4) Uani 1 1 d . . . H6 H 0.0229 -0.0975 0.7562 0.033 Uiso 1 1 calc R . . O11 O -0.01685(7) 0.16646(18) 0.64191(7) 0.0278(3) Uani 1 1 d . . . C12 C -0.07579(11) 0.1809(3) 0.57589(11) 0.0338(4) Uani 1 1 d . . . H12A H -0.0949 0.0452 0.5607 0.041 Uiso 1 1 calc R . . H12B H -0.0508 0.2412 0.5301 0.041 Uiso 1 1 calc R . . C13 C -0.14580(10) 0.3079(3) 0.59811(11) 0.0308(4) Uani 1 1 d . . . C14 C -0.19653(13) 0.2417(4) 0.65512(14) 0.0488(5) Uani 1 1 d . . . H14 H -0.1861 0.1181 0.6814 0.059 Uiso 1 1 calc R . . C15 C -0.26280(15) 0.3571(5) 0.67353(19) 0.0714(8) Uani 1 1 d . . . H15 H -0.2975 0.3121 0.7122 0.086 Uiso 1 1 calc R . . C16 C -0.27752(16) 0.5387(5) 0.6348(2) 0.0767(9) Uani 1 1 d . . . H16 H -0.3224 0.6171 0.6474 0.092 Uiso 1 1 calc R . . C17 C -0.22778(16) 0.6062(4) 0.57829(17) 0.0641(7) Uani 1 1 d . . . H17 H -0.2385 0.7299 0.5522 0.077 Uiso 1 1 calc R . . C18 C -0.16144(13) 0.4908(3) 0.55979(13) 0.0409(5) Uani 1 1 d . . . H18 H -0.1269 0.5368 0.5211 0.049 Uiso 1 1 calc R . . O21 O 0.14224(8) 0.1799(2) 0.58952(8) 0.0351(3) Uani 1 1 d . . . H21 H 0.1579 0.2875 0.6107 0.053 Uiso 1 1 calc R . . O31 O 0.25578(7) -0.1050(2) 0.65311(7) 0.0296(3) Uani 1 1 d . . . C32A C 0.2961(2) -0.1144(7) 0.5794(2) 0.0462(9) Uani 0.759(4) 1 d PU A 1 H32A H 0.2737 -0.0120 0.5422 0.055 Uiso 0.759(4) 1 calc PR A 1 H32B H 0.2880 -0.2479 0.5549 0.055 Uiso 0.759(4) 1 calc PR A 1 C33A C 0.38495(9) -0.0766(4) 0.5970(2) 0.0354(7) Uani 0.759(4) 1 d PGU A 1 C34A C 0.43267(12) -0.2321(3) 0.62961(18) 0.0450(8) Uani 0.759(4) 1 d PGU A 1 H34A H 0.4092 -0.3576 0.6409 0.054 Uiso 0.759(4) 1 calc PR A 1 C35A C 0.51509(12) -0.2021(4) 0.64554(15) 0.0561(9) Uani 0.759(4) 1 d PGU A 1 H35A H 0.5474 -0.3073 0.6676 0.067 Uiso 0.759(4) 1 calc PR A 1 C36A C 0.54979(9) -0.0165(4) 0.62890(18) 0.0588(11) Uani 0.759(4) 1 d PGU A 1 H36A H 0.6055 0.0038 0.6397 0.071 Uiso 0.759(4) 1 calc PR A 1 C37A C 0.50206(14) 0.1391(3) 0.59632(17) 0.0582(10) Uani 0.759(4) 1 d PGU A 1 H37A H 0.5255 0.2646 0.5851 0.070 Uiso 0.759(4) 1 calc PR A 1 C38A C 0.41964(13) 0.1090(3) 0.58040(17) 0.0481(8) Uani 0.759(4) 1 d PGU A 1 H38A H 0.3874 0.2142 0.5584 0.058 Uiso 0.759(4) 1 calc PR A 1 C32B C 0.3082(8) -0.195(2) 0.6008(8) 0.046(2) Uani 0.241(4) 1 d PU A 2 H32C H 0.2828 -0.1944 0.5467 0.056 Uiso 0.241(4) 1 calc PR A 2 H32D H 0.3184 -0.3354 0.6166 0.056 Uiso 0.241(4) 1 calc PR A 2 C33B C 0.3854(3) -0.0831(14) 0.6018(7) 0.043(2) Uani 0.241(4) 1 d PGU A 2 C34B C 0.4583(4) -0.1782(12) 0.6233(6) 0.047(2) Uani 0.241(4) 1 d PGU A 2 H34B H 0.4587 -0.3142 0.6396 0.057 Uiso 0.241(4) 1 calc PR A 2 C35B C 0.5305(3) -0.0720(15) 0.6208(6) 0.057(2) Uani 0.241(4) 1 d PGU A 2 H35B H 0.5798 -0.1362 0.6354 0.069 Uiso 0.241(4) 1 calc PR A 2 C36B C 0.5299(4) 0.1293(15) 0.5968(7) 0.059(2) Uani 0.241(4) 1 d PGU A 2 H36B H 0.5787 0.2011 0.5951 0.071 Uiso 0.241(4) 1 calc PR A 2 C37B C 0.4570(5) 0.2243(12) 0.5753(5) 0.063(2) Uani 0.241(4) 1 d PGU A 2 H37B H 0.4566 0.3604 0.5591 0.076 Uiso 0.241(4) 1 calc PR A 2 C38B C 0.3847(4) 0.1181(14) 0.5778(6) 0.052(2) Uani 0.241(4) 1 d PGU A 2 H38B H 0.3355 0.1824 0.5633 0.062 Uiso 0.241(4) 1 calc PR A 2 O41 O 0.19448(8) -0.48846(19) 0.69381(8) 0.0329(3) Uani 1 1 d . . . H41 H 0.2110 -0.5334 0.7379 0.049 Uiso 1 1 calc R . . O51 O 0.03735(8) -0.43989(19) 0.62155(8) 0.0325(3) Uani 1 1 d . . . H51 H 0.0304 -0.5635 0.6267 0.049 Uiso 1 1 calc R . . O61 O -0.07500(7) -0.2038(2) 0.69874(9) 0.0390(3) Uani 1 1 d . . . H61 H -0.0849 -0.2896 0.6635 0.059 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 C1 0.0273(8) 0.0194(8) 0.0289(8) -0.0022(6) 0.0021(6) 0.0029(6) C2 0.0283(8) 0.0199(8) 0.0269(8) -0.0004(6) 0.0034(6) -0.0020(6) C3 0.0220(7) 0.0226(8) 0.0273(8) -0.0020(6) -0.0007(6) -0.0016(6) C4 0.0285(8) 0.0209(8) 0.0285(8) 0.0006(7) -0.0017(6) 0.0020(7) C5 0.0302(8) 0.0217(8) 0.0310(8) 0.0034(7) 0.0023(7) -0.0029(7) C6 0.0258(8) 0.0259(9) 0.0322(8) -0.0013(7) 0.0052(7) -0.0011(7) O11 0.0298(6) 0.0222(6) 0.0310(6) -0.0041(5) -0.0019(5) 0.0054(5) C12 0.0338(9) 0.0359(10) 0.0311(9) -0.0036(8) -0.0026(7) 0.0077(8) C13 0.0272(8) 0.0311(9) 0.0336(9) -0.0036(7) -0.0029(7) 0.0027(7) C14 0.0442(11) 0.0497(13) 0.0538(13) 0.0022(11) 0.0146(10) -0.0006(10) C15 0.0441(13) 0.091(2) 0.0819(19) -0.0102(18) 0.0266(13) 0.0007(15) C16 0.0430(13) 0.088(2) 0.099(2) -0.0221(19) 0.0026(14) 0.0321(15) C17 0.0597(15) 0.0543(16) 0.0759(18) -0.0017(14) -0.0164(14) 0.0283(13) C18 0.0417(10) 0.0376(11) 0.0424(11) 0.0016(9) -0.0056(9) 0.0067(9) O21 0.0434(7) 0.0228(6) 0.0399(7) 0.0053(6) 0.0094(6) -0.0028(6) O31 0.0235(6) 0.0337(7) 0.0318(6) -0.0049(5) 0.0030(5) -0.0037(5) C32A 0.0297(14) 0.080(3) 0.0291(15) -0.0032(16) 0.0041(11) 0.0030(17) C33A 0.0298(14) 0.0479(16) 0.0292(14) -0.0041(13) 0.0078(12) 0.0017(14) C34A 0.0324(16) 0.0493(18) 0.0545(16) 0.0016(14) 0.0123(14) -0.0014(13) C35A 0.0321(15) 0.069(2) 0.068(2) -0.0015(18) 0.0089(13) 0.0117(15) C36A 0.0322(15) 0.083(3) 0.062(2) -0.0243(19) 0.0147(14) -0.0133(16) C37A 0.048(2) 0.072(2) 0.0565(18) -0.0163(17) 0.0212(17) -0.0214(19) C38A 0.050(2) 0.0523(18) 0.0434(15) -0.0004(14) 0.0127(16) -0.0012(17) C32B 0.038(4) 0.058(5) 0.044(5) -0.015(4) 0.012(4) -0.001(4) C33B 0.036(4) 0.057(4) 0.038(4) -0.006(4) 0.010(4) -0.002(4) C34B 0.031(4) 0.062(4) 0.050(4) -0.006(4) 0.011(3) 0.005(4) C35B 0.032(3) 0.077(4) 0.063(4) -0.019(4) 0.008(3) -0.003(4) C36B 0.038(4) 0.081(5) 0.061(4) -0.026(4) 0.022(4) -0.009(4) C37B 0.060(4) 0.077(5) 0.055(4) -0.018(4) 0.017(4) -0.018(4) C38B 0.048(4) 0.063(4) 0.045(4) -0.010(4) 0.016(4) -0.014(4) O41 0.0359(7) 0.0256(6) 0.0368(7) 0.0029(5) -0.0017(5) 0.0084(5) O51 0.0339(6) 0.0199(6) 0.0429(7) -0.0043(5) -0.0034(5) -0.0031(5) O61 0.0262(6) 0.0351(8) 0.0566(9) -0.0013(7) 0.0107(6) -0.0019(6) _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 C1 O11 1.4342(19) . ? C1 C6 1.525(2) . ? C1 C2 1.526(2) . ? C1 H1 0.9900 . ? C2 O21 1.421(2) . ? C2 C3 1.530(2) . ? C2 H2 0.9900 . ? C3 O31 1.4340(19) . ? C3 C4 1.515(2) . ? C3 H3 0.9900 . ? C4 O41 1.431(2) . ? C4 C5 1.526(2) . ? C4 H4 0.9900 . ? C5 O51 1.428(2) . ? C5 C6 1.522(2) . ? C5 H5 0.9900 . ? C6 O61 1.419(2) . ? C6 H6 0.9900 . ? O11 C12 1.439(2) . ? C12 C13 1.496(2) . ? C12 H12A 0.9800 . ? C12 H12B 0.9800 . ? C13 C14 1.382(3) . ? C13 C18 1.387(3) . ? C14 C15 1.386(3) . ? C14 H14 0.9400 . ? C15 C16 1.381(5) . ? C15 H15 0.9400 . ? C16 C17 1.367(4) . ? C16 H16 0.9400 . ? C17 C18 1.387(3) . ? C17 H17 0.9400 . ? C18 H18 0.9400 . ? O21 H21 0.8300 . ? O31 C32B 1.401(12) . ? O31 C32A 1.443(4) . ? C32A C33A 1.505(4) . ? C32A H32A 0.9800 . ? C32A H32B 0.9800 . ? C33A C34A 1.3900 . ? C33A C38A 1.3900 . ? C34A C35A 1.3900 . ? C34A H34A 0.9400 . ? C35A C36A 1.3900 . ? C35A H35A 0.9400 . ? C36A C37A 1.3900 . ? C36A H36A 0.9400 . ? C37A C38A 1.3900 . ? C37A H37A 0.9400 . ? C38A H38A 0.9400 . ? C32B C33B 1.475(13) . ? C32B H32C 0.9800 . ? C32B H32D 0.9800 . ? C33B C34B 1.3900 . ? C33B C38B 1.3900 . ? C34B C35B 1.3900 . ? C34B H34B 0.9400 . ? C35B C36B 1.3900 . ? C35B H35B 0.9400 . ? C36B C37B 1.3900 . ? C36B H36B 0.9400 . ? C37B C38B 1.3900 . ? C37B H37B 0.9400 . ? C38B H38B 0.9400 . ? O41 H41 0.8300 . ? O51 H51 0.8300 . ? O61 H61 0.8300 . ? 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 O11 C1 C6 110.01(13) . . ? O11 C1 C2 110.60(13) . . ? C6 C1 C2 110.20(14) . . ? O11 C1 H1 108.7 . . ? C6 C1 H1 108.7 . . ? C2 C1 H1 108.7 . . ? O21 C2 C1 109.93(14) . . ? O21 C2 C3 109.66(13) . . ? C1 C2 C3 108.94(13) . . ? O21 C2 H2 109.4 . . ? C1 C2 H2 109.4 . . ? C3 C2 H2 109.4 . . ? O31 C3 C4 109.65(13) . . ? O31 C3 C2 109.42(13) . . ? C4 C3 C2 111.08(13) . . ? O31 C3 H3 108.9 . . ? C4 C3 H3 108.9 . . ? C2 C3 H3 108.9 . . ? O41 C4 C3 109.16(13) . . ? O41 C4 C5 109.97(14) . . ? C3 C4 C5 110.59(13) . . ? O41 C4 H4 109.0 . . ? C3 C4 H4 109.0 . . ? C5 C4 H4 109.0 . . ? O51 C5 C6 106.84(14) . . ? O51 C5 C4 110.16(14) . . ? C6 C5 C4 111.36(14) . . ? O51 C5 H5 109.5 . . ? C6 C5 H5 109.5 . . ? C4 C5 H5 109.5 . . ? O61 C6 C5 111.20(14) . . ? O61 C6 C1 111.74(14) . . ? C5 C6 C1 109.18(13) . . ? O61 C6 H6 108.2 . . ? C5 C6 H6 108.2 . . ? C1 C6 H6 108.2 . . ? C1 O11 C12 112.77(13) . . ? O11 C12 C13 110.21(14) . . ? O11 C12 H12A 109.6 . . ? C13 C12 H12A 109.6 . . ? O11 C12 H12B 109.6 . . ? C13 C12 H12B 109.6 . . ? H12A C12 H12B 108.1 . . ? C14 C13 C18 119.59(19) . . ? C14 C13 C12 120.40(18) . . ? C18 C13 C12 119.98(18) . . ? C13 C14 C15 120.1(2) . . ? C13 C14 H14 120.0 . . ? C15 C14 H14 120.0 . . ? C16 C15 C14 119.6(3) . . ? C16 C15 H15 120.2 . . ? C14 C15 H15 120.2 . . ? C17 C16 C15 121.0(2) . . ? C17 C16 H16 119.5 . . ? C15 C16 H16 119.5 . . ? C16 C17 C18 119.6(3) . . ? C16 C17 H17 120.2 . . ? C18 C17 H17 120.2 . . ? C17 C18 C13 120.2(2) . . ? C17 C18 H18 119.9 . . ? C13 C18 H18 119.9 . . ? C2 O21 H21 109.5 . . ? C32B O31 C3 117.7(5) . . ? C32B O31 C32A 27.0(5) . . ? C3 O31 C32A 112.51(17) . . ? O31 C32A C33A 108.6(2) . . ? O31 C32A H32A 110.0 . . ? C33A C32A H32A 110.0 . . ? O31 C32A H32B 110.0 . . ? C33A C32A H32B 110.0 . . ? H32A C32A H32B 108.3 . . ? C34A C33A C38A 120.0 . . ? C34A C33A C32A 118.8(2) . . ? C38A C33A C32A 121.2(2) . . ? C33A C34A C35A 120.0 . . ? C33A C34A H34A 120.0 . . ? C35A C34A H34A 120.0 . . ? C34A C35A C36A 120.0 . . ? C34A C35A H35A 120.0 . . ? C36A C35A H35A 120.0 . . ? C37A C36A C35A 120.0 . . ? C37A C36A H36A 120.0 . . ? C35A C36A H36A 120.0 . . ? C38A C37A C36A 120.0 . . ? C38A C37A H37A 120.0 . . ? C36A C37A H37A 120.0 . . ? C37A C38A C33A 120.0 . . ? C37A C38A H38A 120.0 . . ? C33A C38A H38A 120.0 . . ? O31 C32B C33B 110.4(9) . . ? O31 C32B H32C 109.6 . . ? C33B C32B H32C 109.6 . . ? O31 C32B H32D 109.6 . . ? C33B C32B H32D 109.6 . . ? H32C C32B H32D 108.1 . . ? C34B C33B C38B 120.0 . . ? C34B C33B C32B 121.1(8) . . ? C38B C33B C32B 118.9(8) . . ? C33B C34B C35B 120.0 . . ? C33B C34B H34B 120.0 . . ? C35B C34B H34B 120.0 . . ? C34B C35B C36B 120.0 . . ? C34B C35B H35B 120.0 . . ? C36B C35B H35B 120.0 . . ? C37B C36B C35B 120.0 . . ? C37B C36B H36B 120.0 . . ? C35B C36B H36B 120.0 . . ? C36B C37B C38B 120.0 . . ? C36B C37B H37B 120.0 . . ? C38B C37B H37B 120.0 . . ? C37B C38B C33B 120.0 . . ? C37B C38B H38B 120.0 . . ? C33B C38B H38B 120.0 . . ? C4 O41 H41 109.5 . . ? C5 O51 H51 109.5 . . ? C6 O61 H61 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 O11 C1 C2 O21 -57.60(17) . . . . ? C6 C1 C2 O21 -179.46(13) . . . . ? O11 C1 C2 C3 -177.79(13) . . . . ? C6 C1 C2 C3 60.35(17) . . . . ? O21 C2 C3 O31 60.12(17) . . . . ? C1 C2 C3 O31 -179.52(12) . . . . ? O21 C2 C3 C4 -178.67(13) . . . . ? C1 C2 C3 C4 -58.31(17) . . . . ? O31 C3 C4 O41 -61.70(17) . . . . ? C2 C3 C4 O41 177.23(13) . . . . ? O31 C3 C4 C5 177.19(13) . . . . ? C2 C3 C4 C5 56.12(18) . . . . ? O41 C4 C5 O51 -58.14(17) . . . . ? C3 C4 C5 O51 62.49(18) . . . . ? O41 C4 C5 C6 -176.50(13) . . . . ? C3 C4 C5 C6 -55.87(18) . . . . ? O51 C5 C6 O61 60.95(17) . . . . ? C4 C5 C6 O61 -178.71(14) . . . . ? O51 C5 C6 C1 -62.79(17) . . . . ? C4 C5 C6 C1 57.55(18) . . . . ? O11 C1 C6 O61 54.28(18) . . . . ? C2 C1 C6 O61 176.49(14) . . . . ? O11 C1 C6 C5 177.71(13) . . . . ? C2 C1 C6 C5 -60.09(18) . . . . ? C6 C1 O11 C12 -108.51(16) . . . . ? C2 C1 O11 C12 129.52(15) . . . . ? C1 O11 C12 C13 154.80(15) . . . . ? O11 C12 C13 C14 -66.8(2) . . . . ? O11 C12 C13 C18 115.02(19) . . . . ? C18 C13 C14 C15 0.3(3) . . . . ? C12 C13 C14 C15 -177.9(2) . . . . ? C13 C14 C15 C16 -0.2(4) . . . . ? C14 C15 C16 C17 0.2(5) . . . . ? C15 C16 C17 C18 -0.2(5) . . . . ? C16 C17 C18 C13 0.2(4) . . . . ? C14 C13 C18 C17 -0.3(3) . . . . ? C12 C13 C18 C17 177.9(2) . . . . ? C4 C3 O31 C32B 101.9(7) . . . . ? C2 C3 O31 C32B -136.0(7) . . . . ? C4 C3 O31 C32A 131.3(2) . . . . ? C2 C3 O31 C32A -106.7(2) . . . . ? C32B O31 C32A C33A -68.9(12) . . . . ? C3 O31 C32A C33A -176.0(2) . . . . ? O31 C32A C33A C34A 77.5(3) . . . . ? O31 C32A C33A C38A -103.3(3) . . . . ? C38A C33A C34A C35A 0.0 . . . . ? C32A C33A C34A C35A 179.2(3) . . . . ? C33A C34A C35A C36A 0.0 . . . . ? C34A C35A C36A C37A 0.0 . . . . ? C35A C36A C37A C38A 0.0 . . . . ? C36A C37A C38A C33A 0.0 . . . . ? C34A C33A C38A C37A 0.0 . . . . ? C32A C33A C38A C37A -179.2(3) . . . . ? C3 O31 C32B C33B 161.7(7) . . . . ? C32A O31 C32B C33B 76.2(14) . . . . ? O31 C32B C33B C34B 120.5(9) . . . . ? O31 C32B C33B C38B -62.0(12) . . . . ? C38B C33B C34B C35B 0.0 . . . . ? C32B C33B C34B C35B 177.5(11) . . . . ? C33B C34B C35B C36B 0.0 . . . . ? C34B C35B C36B C37B 0.0 . . . . ? C35B C36B C37B C38B 0.0 . . . . ? C36B C37B C38B C33B 0.0 . . . . ? C34B C33B C38B C37B 0.0 . . . . ? C32B C33B C38B C37B -177.5(11) . . . . ? loop_ _geom_hbond_atom_site_label_D _geom_hbond_atom_site_label_H _geom_hbond_atom_site_label_A _geom_hbond_distance_DH _geom_hbond_distance_HA _geom_hbond_distance_DA _geom_hbond_angle_DHA _geom_hbond_site_symmetry_A O21 H21 O41 0.83 2.10 2.9078(19) 163.7 1_565 O41 H41 O31 0.83 1.94 2.7667(17) 172.3 2_546 O51 H51 O11 0.83 1.97 2.7801(18) 164.3 1_545 O61 H61 O51 0.83 2.40 2.8038(19) 110.9 . _diffrn_measured_fraction_theta_max 0.984 _diffrn_reflns_theta_full 28.29 _diffrn_measured_fraction_theta_full 0.984 _refine_diff_density_max 0.276 _refine_diff_density_min -0.204 _refine_diff_density_rms 0.046 _database_code_depnum_ccdc_archive 'CCDC 938829' ####################################################################### # # 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_fro6596 _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C12 H20 O6' _chemical_formula_weight 260.28 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 '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 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M C2/c loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y, -z+1/2' 'x+1/2, y+1/2, z' '-x+1/2, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y, z-1/2' '-x+1/2, -y+1/2, -z' 'x+1/2, -y+1/2, z-1/2' _cell_length_a 21.6206(4) _cell_length_b 11.0216(2) _cell_length_c 23.9782(5) _cell_angle_alpha 90.00 _cell_angle_beta 108.049(1) _cell_angle_gamma 90.00 _cell_volume 5432.68(18) _cell_formula_units_Z 16 _cell_measurement_temperature 223(2) _cell_measurement_reflns_used 4861 _cell_measurement_theta_min 4.08 _cell_measurement_theta_max 28.28 _exptl_crystal_description plate _exptl_crystal_colour colourless _exptl_crystal_size_max 0.20 _exptl_crystal_size_mid 0.20 _exptl_crystal_size_min 0.07 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.273 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 2240 _exptl_absorpt_coefficient_mu 0.102 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.9799 _exptl_absorpt_correction_T_max 0.9929 _exptl_absorpt_process_details 'Denzo (Otwinowski, Borek, Majewski & Minor, 2003)' _exptl_special_details ; ? ; _diffrn_ambient_temperature 223(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'rotating anode Nonius FR591' _diffrn_radiation_monochromator 'Montel mirror' _diffrn_measurement_device_type 'Nonius KappaCCD APEXII' _diffrn_measurement_method '\w and \f scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 15088 _diffrn_reflns_av_R_equivalents 0.037 _diffrn_reflns_av_sigmaI/netI 0.0449 _diffrn_reflns_limit_h_min -28 _diffrn_reflns_limit_h_max 28 _diffrn_reflns_limit_k_min -14 _diffrn_reflns_limit_k_max 13 _diffrn_reflns_limit_l_min -31 _diffrn_reflns_limit_l_max 31 _diffrn_reflns_theta_min 4.11 _diffrn_reflns_theta_max 28.35 _reflns_number_total 6704 _reflns_number_gt 4318 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Collect (Nonius B.V., 1998)' _computing_cell_refinement 'Collect (Nonius B.V., 1998)' _computing_data_reduction 'Denzo-SMN (Otwinowski & Minor, 1997)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'XP (BrukerAXS, 2000)' _computing_publication_material 'SHELXL-97 (Sheldrick, 1997)' _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^)+(0.0735P)^2^+12.7218P] 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 6704 _refine_ls_number_parameters 363 _refine_ls_number_restraints 183 _refine_ls_R_factor_all 0.1254 _refine_ls_R_factor_gt 0.0841 _refine_ls_wR_factor_ref 0.2275 _refine_ls_wR_factor_gt 0.1943 _refine_ls_goodness_of_fit_ref 1.034 _refine_ls_restrained_S_all 1.103 _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 C1A C 0.34455(16) 0.4525(3) 0.11919(13) 0.0492(8) Uani 1 1 d . A . H1A H 0.3772 0.4022 0.1086 0.059 Uiso 1 1 calc R . . O11A O 0.35208(11) 0.4374(2) 0.18031(9) 0.0585(6) Uani 1 1 d D . . C12A C 0.4149(6) 0.4331(14) 0.2251(6) 0.0669(17) Uani 0.264(7) 1 d PDU A 1 H12A H 0.4188 0.4993 0.2533 0.080 Uiso 0.264(7) 1 calc PR A 1 H12B H 0.4499 0.4408 0.2074 0.080 Uiso 0.264(7) 1 calc PR A 1 C13A C 0.4186(8) 0.3159(14) 0.2542(6) 0.0716(17) Uani 0.264(7) 1 d PDU A 1 H13A H 0.4074 0.2444 0.2320 0.086 Uiso 0.264(7) 1 calc PR A 1 C14A C 0.4379(18) 0.311(2) 0.3127(7) 0.088(3) Uani 0.264(7) 1 d PDU A 1 H14A H 0.4490 0.3827 0.3348 0.105 Uiso 0.264(7) 1 calc PR A 1 H14B H 0.4405 0.2359 0.3318 0.105 Uiso 0.264(7) 1 calc PR A 1 C12C C 0.4137(3) 0.3813(7) 0.2118(2) 0.0669(17) Uani 0.736(7) 1 d PDU A 2 H12E H 0.4498 0.4294 0.2068 0.080 Uiso 0.736(7) 1 calc PR A 2 H12F H 0.4161 0.2996 0.1965 0.080 Uiso 0.736(7) 1 calc PR A 2 C13C C 0.4183(3) 0.3750(6) 0.2740(2) 0.0716(17) Uani 0.736(7) 1 d PDU A 2 H13C H 0.4112 0.4445 0.2938 0.086 Uiso 0.736(7) 1 calc PR A 2 C14C C 0.4329(6) 0.2690(7) 0.3022(3) 0.088(3) Uani 0.736(7) 1 d PDU A 2 H14E H 0.4400 0.1998 0.2821 0.105 Uiso 0.736(7) 1 calc PR A 2 H14F H 0.4360 0.2637 0.3421 0.105 Uiso 0.736(7) 1 calc PR A 2 C2A C 0.35361(14) 0.5848(3) 0.10567(12) 0.0462(7) Uani 1 1 d . . . H2A H 0.3236 0.6338 0.1205 0.055 Uiso 1 1 calc R A . O21A O 0.41807(12) 0.6244(3) 0.13502(11) 0.0763(9) Uani 1 1 d . A . H21A H 0.4444 0.5750 0.1292 0.114 Uiso 1 1 calc R . . C3A C 0.33567(15) 0.6058(3) 0.03946(13) 0.0444(7) Uani 1 1 d . A . H3A H 0.3637 0.5558 0.0228 0.053 Uiso 1 1 calc R . . O31A O 0.34473(12) 0.7312(2) 0.02982(10) 0.0593(6) Uani 1 1 d D . . C32A C 0.3925(3) 0.7716(7) 0.0048(3) 0.0663(17) Uani 0.633(6) 1 d PDU A 1 H32A H 0.4295 0.7155 0.0154 0.080 Uiso 0.633(6) 1 calc PR A 1 H32B H 0.4083 0.8518 0.0204 0.080 Uiso 0.633(6) 1 calc PR A 1 C33A C 0.3656(3) 0.7783(6) -0.0589(3) 0.0698(15) Uani 0.633(6) 1 d PDU A 1 H33A H 0.3482 0.7068 -0.0790 0.084 Uiso 0.633(6) 1 calc PR A 1 C34A C 0.3637(5) 0.8774(8) -0.0907(4) 0.081(2) Uani 0.633(6) 1 d PDU A 1 H34A H 0.3806 0.9508 -0.0722 0.097 Uiso 0.633(6) 1 calc PR A 1 H34B H 0.3454 0.8744 -0.1317 0.097 Uiso 0.633(6) 1 calc PR A 1 C32C C 0.3763(6) 0.7340(9) -0.0164(5) 0.0663(17) Uani 0.367(6) 1 d PDU A 2 H32E H 0.4155 0.6835 -0.0046 0.080 Uiso 0.367(6) 1 calc PR A 2 H32F H 0.3466 0.7003 -0.0527 0.080 Uiso 0.367(6) 1 calc PR A 2 C33C C 0.3938(5) 0.8572(9) -0.0271(5) 0.0698(15) Uani 0.367(6) 1 d PDU A 2 H33C H 0.4158 0.9021 0.0065 0.084 Uiso 0.367(6) 1 calc PR A 2 C34C C 0.3833(9) 0.9142(15) -0.0769(6) 0.081(2) Uani 0.367(6) 1 d PDU A 2 H34E H 0.3616 0.8748 -0.1123 0.097 Uiso 0.367(6) 1 calc PR A 2 H34F H 0.3975 0.9947 -0.0773 0.097 Uiso 0.367(6) 1 calc PR A 2 C4A C 0.26518(15) 0.5698(3) 0.01248(12) 0.0440(7) Uani 1 1 d . . . H4A H 0.2390 0.6133 0.0335 0.053 Uiso 1 1 calc R A . O41A O 0.24102(12) 0.6009(2) -0.04818(9) 0.0569(6) Uani 1 1 d . A . H41A H 0.2095 0.6474 -0.0537 0.085 Uiso 1 1 calc R . . C5A C 0.25804(18) 0.4342(3) 0.02053(13) 0.0528(8) Uani 1 1 d . A . H5A H 0.2123 0.4096 0.0013 0.063 Uiso 1 1 calc R . . O51A O 0.29978(15) 0.3693(2) -0.00461(11) 0.0715(8) Uani 1 1 d . . . H51A H 0.2776 0.3253 -0.0315 0.107 Uiso 1 1 calc R A . C6A C 0.27702(18) 0.4073(3) 0.08647(14) 0.0507(8) Uani 1 1 d . . . H6A H 0.2455 0.4482 0.1026 0.061 Uiso 1 1 calc R A . O61A O 0.27240(18) 0.2797(2) 0.09379(12) 0.0786(9) Uani 1 1 d . A . H61A H 0.2623 0.2661 0.1239 0.118 Uiso 1 1 calc R . . C1B C 0.14375(16) 0.3709(3) 0.28293(12) 0.0451(7) Uani 1 1 d . B . H1B H 0.1368 0.4453 0.2587 0.054 Uiso 1 1 calc R . . O11B O 0.11357(12) 0.3852(2) 0.32820(9) 0.0530(6) Uani 1 1 d . . . C12B C 0.0883(2) 0.5042(4) 0.33087(18) 0.0745(12) Uani 1 1 d . . . H12C H 0.1243 0.5625 0.3403 0.089 Uiso 1 1 calc R . . H12D H 0.0584 0.5254 0.2922 0.089 Uiso 1 1 calc R . . C13B C 0.0548(3) 0.5141(5) 0.3736(2) 0.0884(14) Uani 1 1 d . . . H13B H 0.0234 0.4545 0.3725 0.106 Uiso 1 1 calc R . . C14B C 0.0636(3) 0.5967(6) 0.4134(2) 0.120(2) Uani 1 1 d . . . H14C H 0.0945 0.6582 0.4163 0.143 Uiso 1 1 calc R . . H14D H 0.0390 0.5953 0.4396 0.143 Uiso 1 1 calc R . . C2B C 0.11240(16) 0.2644(3) 0.24480(14) 0.0524(8) Uani 1 1 d . . . H2B H 0.1157 0.1923 0.2702 0.063 Uiso 1 1 calc R . . O21B O 0.04511(13) 0.2883(4) 0.21552(13) 0.0856(10) Uani 1 1 d . . . H21B H 0.0375 0.3613 0.2189 0.128 Uiso 1 1 calc R . . C3B C 0.14679(16) 0.2367(3) 0.19968(14) 0.0523(8) Uani 1 1 d . B . H3B H 0.1420 0.3062 0.1725 0.063 Uiso 1 1 calc R . . O31B O 0.11689(15) 0.1317(3) 0.16804(14) 0.0869(10) Uani 1 1 d D . . C32B C 0.0848(7) 0.1659(10) 0.1073(3) 0.099(3) Uani 0.454(5) 1 d PDU B 1 H32C H 0.0538 0.2310 0.1067 0.119 Uiso 0.454(5) 1 calc PR B 1 H32D H 0.1177 0.1991 0.0910 0.119 Uiso 0.454(5) 1 calc PR B 1 C33B C 0.0507(6) 0.0695(11) 0.0693(4) 0.109(3) Uani 0.454(5) 1 d PDU B 1 H33B H 0.0339 0.0057 0.0863 0.130 Uiso 0.454(5) 1 calc PR B 1 C34B C 0.0415(7) 0.0650(16) 0.0125(5) 0.144(4) Uani 0.454(5) 1 d PDU B 1 H34C H 0.0576 0.1273 -0.0059 0.173 Uiso 0.454(5) 1 calc PR B 1 H34D H 0.0188 -0.0005 -0.0097 0.173 Uiso 0.454(5) 1 calc PR B 1 C32D C 0.1133(5) 0.1129(9) 0.1089(3) 0.099(3) Uani 0.546(5) 1 d PDU B 2 H32G H 0.1005 0.0296 0.0963 0.119 Uiso 0.546(5) 1 calc PR B 2 H32H H 0.1547 0.1317 0.1020 0.119 Uiso 0.546(5) 1 calc PR B 2 C33D C 0.0631(5) 0.1992(10) 0.0801(4) 0.109(3) Uani 0.546(5) 1 d PDU B 2 H33D H 0.0249 0.2042 0.0909 0.130 Uiso 0.546(5) 1 calc PR B 2 C34D C 0.0710(7) 0.2706(12) 0.0388(5) 0.144(4) Uani 0.546(5) 1 d PDU B 2 H34G H 0.1091 0.2656 0.0281 0.173 Uiso 0.546(5) 1 calc PR B 2 H34H H 0.0384 0.3267 0.0201 0.173 Uiso 0.546(5) 1 calc PR B 2 C4B C 0.21820(16) 0.2128(3) 0.23047(14) 0.0451(7) Uani 1 1 d . . . H4B H 0.2220 0.1431 0.2574 0.054 Uiso 1 1 calc R B . O41B O 0.25269(13) 0.18507(19) 0.19027(11) 0.0568(6) Uani 1 1 d . B . H41B H 0.2500 0.1113 0.1831 0.085 Uiso 1 1 calc R . . C5B C 0.25010(15) 0.3221(3) 0.26607(13) 0.0418(6) Uani 1 1 d . B . H5B H 0.2964 0.3036 0.2864 0.050 Uiso 1 1 calc R . . O51B O 0.24593(11) 0.42524(18) 0.22912(9) 0.0461(5) Uani 1 1 d . . . H51B H 0.2780 0.4268 0.2171 0.069 Uiso 1 1 calc R B . C6B C 0.21634(15) 0.3510(3) 0.31121(12) 0.0420(6) Uani 1 1 d . . . H6B H 0.2223 0.2810 0.3382 0.050 Uiso 1 1 calc R B . O61B O 0.24673(13) 0.4537(2) 0.34444(9) 0.0549(6) Uani 1 1 d . B . H61B H 0.2441 0.4486 0.3782 0.082 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 C1A 0.0561(18) 0.0562(18) 0.0419(16) 0.0095(14) 0.0247(14) 0.0198(15) O11A 0.0523(13) 0.0856(18) 0.0417(11) 0.0204(12) 0.0203(10) 0.0198(12) C12A 0.056(2) 0.086(4) 0.060(3) 0.023(3) 0.020(2) 0.026(3) C13A 0.058(2) 0.094(4) 0.063(3) 0.018(3) 0.018(2) 0.020(3) C14A 0.073(3) 0.097(6) 0.090(4) 0.044(4) 0.021(3) 0.004(5) C12C 0.056(2) 0.086(4) 0.060(3) 0.023(3) 0.020(2) 0.026(3) C13C 0.058(2) 0.094(4) 0.063(3) 0.018(3) 0.018(2) 0.020(3) C14C 0.073(3) 0.097(6) 0.090(4) 0.044(4) 0.021(3) 0.004(5) C2A 0.0413(16) 0.0606(19) 0.0378(15) 0.0012(14) 0.0138(12) 0.0040(14) O21A 0.0455(13) 0.129(3) 0.0514(14) 0.0111(16) 0.0107(11) -0.0066(15) C3A 0.0538(18) 0.0438(16) 0.0398(15) 0.0029(12) 0.0206(13) 0.0082(13) O31A 0.0788(17) 0.0501(13) 0.0509(13) 0.0058(11) 0.0228(12) -0.0025(12) C32A 0.051(3) 0.061(4) 0.086(4) 0.014(3) 0.020(3) -0.011(3) C33A 0.071(3) 0.077(3) 0.074(3) -0.005(3) 0.041(3) -0.002(3) C34A 0.083(6) 0.087(5) 0.089(4) 0.010(4) 0.050(4) -0.001(4) C32C 0.051(3) 0.061(4) 0.086(4) 0.014(3) 0.020(3) -0.011(3) C33C 0.071(3) 0.077(3) 0.074(3) -0.005(3) 0.041(3) -0.002(3) C34C 0.083(6) 0.087(5) 0.089(4) 0.010(4) 0.050(4) -0.001(4) C4A 0.0545(18) 0.0498(17) 0.0291(13) -0.0007(12) 0.0153(12) 0.0059(14) O41A 0.0656(15) 0.0725(16) 0.0322(10) 0.0038(10) 0.0146(10) 0.0131(12) C5A 0.072(2) 0.0523(18) 0.0387(16) -0.0089(14) 0.0239(15) -0.0058(16) O51A 0.117(2) 0.0541(15) 0.0593(15) -0.0150(12) 0.0496(15) 0.0008(15) C6A 0.076(2) 0.0404(16) 0.0440(16) -0.0006(13) 0.0305(16) 0.0059(15) O61A 0.149(3) 0.0439(13) 0.0591(16) -0.0035(12) 0.0556(17) -0.0065(15) C1B 0.0602(19) 0.0425(15) 0.0370(14) 0.0042(12) 0.0216(13) 0.0086(14) O11B 0.0718(15) 0.0485(12) 0.0484(12) 0.0041(10) 0.0329(11) 0.0110(11) C12B 0.102(3) 0.065(2) 0.068(2) 0.0095(19) 0.043(2) 0.035(2) C13B 0.108(4) 0.085(3) 0.087(3) 0.005(3) 0.051(3) 0.030(3) C14B 0.165(6) 0.119(5) 0.089(3) 0.001(3) 0.060(4) 0.067(4) C2B 0.0481(18) 0.063(2) 0.0475(17) -0.0054(15) 0.0176(14) -0.0005(15) O21B 0.0504(15) 0.130(3) 0.0703(17) -0.0298(19) 0.0102(13) 0.0104(16) C3B 0.0567(19) 0.0532(18) 0.0500(18) -0.0171(15) 0.0210(15) -0.0097(15) O31B 0.091(2) 0.089(2) 0.089(2) -0.0505(17) 0.0398(17) -0.0301(17) C32B 0.102(5) 0.093(5) 0.094(4) -0.048(4) 0.018(4) 0.000(4) C33B 0.112(5) 0.118(5) 0.085(4) 0.001(4) 0.013(4) 0.004(5) C34B 0.136(6) 0.151(6) 0.142(6) 0.012(5) 0.039(5) 0.003(5) C32D 0.102(5) 0.093(5) 0.094(4) -0.048(4) 0.018(4) 0.000(4) C33D 0.112(5) 0.118(5) 0.085(4) 0.001(4) 0.013(4) 0.004(5) C34D 0.136(6) 0.151(6) 0.142(6) 0.012(5) 0.039(5) 0.003(5) C4B 0.0617(19) 0.0325(14) 0.0503(17) 0.0003(13) 0.0307(15) 0.0016(13) O41B 0.0782(16) 0.0364(11) 0.0714(15) -0.0034(11) 0.0459(13) 0.0021(11) C5B 0.0483(16) 0.0350(14) 0.0441(15) 0.0078(12) 0.0172(13) 0.0022(12) O51B 0.0647(14) 0.0346(10) 0.0471(11) 0.0071(9) 0.0290(10) 0.0010(10) C6B 0.0580(18) 0.0328(13) 0.0361(14) 0.0051(11) 0.0159(12) -0.0025(12) O61B 0.0863(17) 0.0443(12) 0.0381(11) -0.0031(9) 0.0252(11) -0.0187(11) _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 C1A O11A 1.433(3) . ? C1A C6A 1.512(5) . ? C1A C2A 1.520(5) . ? C1A H1A 0.9900 . ? O11A C12A 1.447(8) . ? O11A C12C 1.451(5) . ? C12A C13A 1.459(9) . ? C12A H12A 0.9800 . ? C12A H12B 0.9800 . ? C13A C14A 1.335(9) . ? C13A H13A 0.9400 . ? C14A H14A 0.9400 . ? C14A H14B 0.9400 . ? C12C C13C 1.465(6) . ? C12C H12E 0.9800 . ? C12C H12F 0.9800 . ? C13C C14C 1.337(7) . ? C13C H13C 0.9400 . ? C14C H14E 0.9400 . ? C14C H14F 0.9400 . ? C2A O21A 1.421(4) . ? C2A C3A 1.531(4) . ? C2A H2A 0.9900 . ? O21A H21A 0.8300 . ? C3A O31A 1.425(4) . ? C3A C4A 1.513(4) . ? C3A H3A 0.9900 . ? O31A C32A 1.418(5) . ? O31A C32C 1.470(8) . ? C32A C33A 1.458(7) . ? C32A H32A 0.9800 . ? C32A H32B 0.9800 . ? C33A C34A 1.325(7) . ? C33A H33A 0.9400 . ? C34A H34A 0.9400 . ? C34A H34B 0.9400 . ? C32C C33C 1.453(8) . ? C32C H32E 0.9800 . ? C32C H32F 0.9800 . ? C33C C34C 1.305(9) . ? C33C H33C 0.9400 . ? C34C H34E 0.9400 . ? C34C H34F 0.9400 . ? C4A O41A 1.427(3) . ? C4A C5A 1.520(4) . ? C4A H4A 0.9900 . ? O41A H41A 0.8300 . ? C5A O51A 1.424(4) . ? C5A C6A 1.534(4) . ? C5A H5A 0.9900 . ? O51A H51A 0.8300 . ? C6A O61A 1.424(4) . ? C6A H6A 0.9900 . ? O61A H61A 0.8300 . ? C1B O11B 1.438(3) . ? C1B C2B 1.512(5) . ? C1B C6B 1.520(4) . ? C1B H1B 0.9900 . ? O11B C12B 1.430(4) . ? C12B C13B 1.429(6) . ? C12B H12C 0.9800 . ? C12B H12D 0.9800 . ? C13B C14B 1.291(7) . ? C13B H13B 0.9400 . ? C14B H14C 0.9400 . ? C14B H14D 0.9400 . ? C2B O21B 1.430(4) . ? C2B C3B 1.521(4) . ? C2B H2B 0.9900 . ? O21B H21B 0.8300 . ? C3B O31B 1.425(4) . ? C3B C4B 1.514(5) . ? C3B H3B 0.9900 . ? O31B C32D 1.412(7) . ? O31B C32B 1.456(8) . ? C32B C33B 1.445(8) . ? C32B H32C 0.9800 . ? C32B H32D 0.9800 . ? C33B C34B 1.314(9) . ? C33B H33B 0.9400 . ? C34B H34C 0.9400 . ? C34B H34D 0.9400 . ? C32D C33D 1.447(8) . ? C32D H32G 0.9800 . ? C32D H32H 0.9800 . ? C33D C34D 1.315(9) . ? C33D H33D 0.9400 . ? C34D H34G 0.9400 . ? C34D H34H 0.9400 . ? C4B O41B 1.423(3) . ? C4B C5B 1.513(4) . ? C4B H4B 0.9900 . ? O41B H41B 0.8300 . ? C5B O51B 1.427(3) . ? C5B C6B 1.515(4) . ? C5B H5B 0.9900 . ? O51B H51B 0.8300 . ? C6B O61B 1.422(3) . ? C6B H6B 0.9900 . ? O61B H61B 0.8300 . ? 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 O11A C1A C6A 106.2(2) . . ? O11A C1A C2A 110.4(3) . . ? C6A C1A C2A 111.9(3) . . ? O11A C1A H1A 109.5 . . ? C6A C1A H1A 109.5 . . ? C2A C1A H1A 109.5 . . ? C1A O11A C12A 123.1(8) . . ? C1A O11A C12C 112.1(3) . . ? C12A O11A C12C 26.0(7) . . ? O11A C12A C13A 106.5(9) . . ? O11A C12A H12A 110.4 . . ? C13A C12A H12A 110.4 . . ? O11A C12A H12B 110.4 . . ? C13A C12A H12B 110.4 . . ? H12A C12A H12B 108.6 . . ? C14A C13A C12A 119.4(14) . . ? C14A C13A H13A 120.3 . . ? C12A C13A H13A 120.3 . . ? C13A C14A H14A 120.0 . . ? C13A C14A H14B 120.0 . . ? H14A C14A H14B 120.0 . . ? O11A C12C C13C 108.2(4) . . ? O11A C12C H12E 110.1 . . ? C13C C12C H12E 110.1 . . ? O11A C12C H12F 110.1 . . ? C13C C12C H12F 110.1 . . ? H12E C12C H12F 108.4 . . ? C14C C13C C12C 119.1(8) . . ? C14C C13C H13C 120.4 . . ? C12C C13C H13C 120.4 . . ? C13C C14C H14E 120.0 . . ? C13C C14C H14F 120.0 . . ? H14E C14C H14F 120.0 . . ? O21A C2A C1A 111.1(3) . . ? O21A C2A C3A 111.2(2) . . ? C1A C2A C3A 111.0(3) . . ? O21A C2A H2A 107.8 . . ? C1A C2A H2A 107.8 . . ? C3A C2A H2A 107.8 . . ? C2A O21A H21A 109.5 . . ? O31A C3A C4A 110.9(2) . . ? O31A C3A C2A 108.1(2) . . ? C4A C3A C2A 107.6(2) . . ? O31A C3A H3A 110.1 . . ? C4A C3A H3A 110.1 . . ? C2A C3A H3A 110.1 . . ? C32A O31A C3A 121.9(4) . . ? C32A O31A C32C 26.5(4) . . ? C3A O31A C32C 105.2(4) . . ? O31A C32A C33A 110.6(5) . . ? O31A C32A H32A 109.5 . . ? C33A C32A H32A 109.5 . . ? O31A C32A H32B 109.5 . . ? C33A C32A H32B 109.5 . . ? H32A C32A H32B 108.1 . . ? C34A C33A C32A 125.1(7) . . ? C34A C33A H33A 117.4 . . ? C32A C33A H33A 117.4 . . ? C33A C34A H34A 120.0 . . ? C33A C34A H34B 120.0 . . ? H34A C34A H34B 120.0 . . ? C33C C32C O31A 111.1(7) . . ? C33C C32C H32E 109.4 . . ? O31A C32C H32E 109.4 . . ? C33C C32C H32F 109.4 . . ? O31A C32C H32F 109.4 . . ? H32E C32C H32F 108.0 . . ? C34C C33C C32C 129.1(11) . . ? C34C C33C H33C 115.5 . . ? C32C C33C H33C 115.5 . . ? C33C C34C H34E 120.0 . . ? C33C C34C H34F 120.0 . . ? H34E C34C H34F 120.0 . . ? O41A C4A C3A 112.0(2) . . ? O41A C4A C5A 110.3(3) . . ? C3A C4A C5A 109.4(3) . . ? O41A C4A H4A 108.4 . . ? C3A C4A H4A 108.4 . . ? C5A C4A H4A 108.4 . . ? C4A O41A H41A 109.5 . . ? O51A C5A C4A 109.7(3) . . ? O51A C5A C6A 109.7(3) . . ? C4A C5A C6A 108.4(2) . . ? O51A C5A H5A 109.7 . . ? C4A C5A H5A 109.7 . . ? C6A C5A H5A 109.7 . . ? C5A O51A H51A 109.5 . . ? O61A C6A C1A 110.8(3) . . ? O61A C6A C5A 108.1(3) . . ? C1A C6A C5A 112.2(3) . . ? O61A C6A H6A 108.5 . . ? C1A C6A H6A 108.5 . . ? C5A C6A H6A 108.5 . . ? C6A O61A H61A 109.5 . . ? O11B C1B C2B 108.6(3) . . ? O11B C1B C6B 109.0(2) . . ? C2B C1B C6B 111.4(2) . . ? O11B C1B H1B 109.3 . . ? C2B C1B H1B 109.3 . . ? C6B C1B H1B 109.3 . . ? C12B O11B C1B 113.8(2) . . ? C13B C12B O11B 112.8(3) . . ? C13B C12B H12C 109.0 . . ? O11B C12B H12C 109.0 . . ? C13B C12B H12D 109.0 . . ? O11B C12B H12D 109.0 . . ? H12C C12B H12D 107.8 . . ? C14B C13B C12B 126.4(6) . . ? C14B C13B H13B 116.8 . . ? C12B C13B H13B 116.8 . . ? C13B C14B H14C 120.0 . . ? C13B C14B H14D 120.0 . . ? H14C C14B H14D 120.0 . . ? O21B C2B C1B 110.6(3) . . ? O21B C2B C3B 109.6(3) . . ? C1B C2B C3B 111.0(3) . . ? O21B C2B H2B 108.5 . . ? C1B C2B H2B 108.5 . . ? C3B C2B H2B 108.5 . . ? C2B O21B H21B 109.5 . . ? O31B C3B C4B 110.1(3) . . ? O31B C3B C2B 107.5(3) . . ? C4B C3B C2B 109.7(3) . . ? O31B C3B H3B 109.8 . . ? C4B C3B H3B 109.8 . . ? C2B C3B H3B 109.8 . . ? C32D O31B C3B 121.9(5) . . ? C32D O31B C32B 34.1(5) . . ? C3B O31B C32B 108.6(5) . . ? C33B C32B O31B 115.6(8) . . ? C33B C32B H32C 108.4 . . ? O31B C32B H32C 108.4 . . ? C33B C32B H32D 108.4 . . ? O31B C32B H32D 108.4 . . ? H32C C32B H32D 107.4 . . ? C34B C33B C32B 124.4(11) . . ? C34B C33B H33B 117.8 . . ? C32B C33B H33B 117.8 . . ? C33B C34B H34C 120.0 . . ? C33B C34B H34D 120.0 . . ? H34C C34B H34D 120.0 . . ? O31B C32D C33D 100.5(6) . . ? O31B C32D H32G 111.7 . . ? C33D C32D H32G 111.7 . . ? O31B C32D H32H 111.7 . . ? C33D C32D H32H 111.7 . . ? H32G C32D H32H 109.4 . . ? C34D C33D C32D 120.0(10) . . ? C34D C33D H33D 120.0 . . ? C32D C33D H33D 120.0 . . ? C33D C34D H34G 120.0 . . ? C33D C34D H34H 120.0 . . ? H34G C34D H34H 120.0 . . ? O41B C4B C5B 108.1(2) . . ? O41B C4B C3B 112.1(3) . . ? C5B C4B C3B 110.7(2) . . ? O41B C4B H4B 108.6 . . ? C5B C4B H4B 108.6 . . ? C3B C4B H4B 108.6 . . ? C4B O41B H41B 109.5 . . ? O51B C5B C4B 110.7(2) . . ? O51B C5B C6B 108.9(2) . . ? C4B C5B C6B 109.5(2) . . ? O51B C5B H5B 109.2 . . ? C4B C5B H5B 109.2 . . ? C6B C5B H5B 109.2 . . ? C5B O51B H51B 109.5 . . ? O61B C6B C5B 109.0(2) . . ? O61B C6B C1B 111.7(2) . . ? C5B C6B C1B 111.8(2) . . ? O61B C6B H6B 108.1 . . ? C5B C6B H6B 108.1 . . ? C1B C6B H6B 108.1 . . ? C6B O61B H61B 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 C6A C1A O11A C12A 159.8(8) . . . . ? C2A C1A O11A C12A -78.8(8) . . . . ? C6A C1A O11A C12C 133.1(4) . . . . ? C2A C1A O11A C12C -105.4(4) . . . . ? C1A O11A C12A C13A -120.6(11) . . . . ? C12C O11A C12A C13A -48.8(13) . . . . ? O11A C12A C13A C14A -132(2) . . . . ? C1A O11A C12C C13C 177.4(5) . . . . ? C12A O11A C12C C13C 56.6(16) . . . . ? O11A C12C C13C C14C 128.6(7) . . . . ? O11A C1A C2A O21A 64.3(3) . . . . ? C6A C1A C2A O21A -177.8(2) . . . . ? O11A C1A C2A C3A -171.4(2) . . . . ? C6A C1A C2A C3A -53.4(3) . . . . ? O21A C2A C3A O31A -56.2(3) . . . . ? C1A C2A C3A O31A 179.6(2) . . . . ? O21A C2A C3A C4A -176.0(3) . . . . ? C1A C2A C3A C4A 59.8(3) . . . . ? C4A C3A O31A C32A -127.5(4) . . . . ? C2A C3A O31A C32A 114.8(4) . . . . ? C4A C3A O31A C32C -104.9(6) . . . . ? C2A C3A O31A C32C 137.4(6) . . . . ? C3A O31A C32A C33A 90.2(6) . . . . ? C32C O31A C32A C33A 33.9(12) . . . . ? O31A C32A C33A C34A 121.7(8) . . . . ? C32A O31A C32C C33C -42.0(10) . . . . ? C3A O31A C32C C33C -174.9(8) . . . . ? O31A C32C C33C C34C -131.8(15) . . . . ? O31A C3A C4A O41A 54.2(3) . . . . ? C2A C3A C4A O41A 172.2(2) . . . . ? O31A C3A C4A C5A 176.8(2) . . . . ? C2A C3A C4A C5A -65.2(3) . . . . ? O41A C4A C5A O51A 66.8(3) . . . . ? C3A C4A C5A O51A -56.8(3) . . . . ? O41A C4A C5A C6A -173.4(3) . . . . ? C3A C4A C5A C6A 63.0(3) . . . . ? O11A C1A C6A O61A -67.1(3) . . . . ? C2A C1A C6A O61A 172.4(2) . . . . ? O11A C1A C6A C5A 171.9(2) . . . . ? C2A C1A C6A C5A 51.4(3) . . . . ? O51A C5A C6A O61A -58.2(4) . . . . ? C4A C5A C6A O61A -178.0(3) . . . . ? O51A C5A C6A C1A 64.2(3) . . . . ? C4A C5A C6A C1A -55.6(4) . . . . ? C2B C1B O11B C12B -125.6(3) . . . . ? C6B C1B O11B C12B 112.9(3) . . . . ? C1B O11B C12B C13B 176.1(4) . . . . ? O11B C12B C13B C14B 130.3(5) . . . . ? O11B C1B C2B O21B 63.8(3) . . . . ? C6B C1B C2B O21B -176.1(3) . . . . ? O11B C1B C2B C3B -174.4(3) . . . . ? C6B C1B C2B C3B -54.3(4) . . . . ? O21B C2B C3B O31B -60.9(4) . . . . ? C1B C2B C3B O31B 176.7(3) . . . . ? O21B C2B C3B C4B 179.4(3) . . . . ? C1B C2B C3B C4B 56.9(4) . . . . ? C4B C3B O31B C32D -90.9(6) . . . . ? C2B C3B O31B C32D 149.6(5) . . . . ? C4B C3B O31B C32B -125.8(7) . . . . ? C2B C3B O31B C32B 114.7(7) . . . . ? C32D O31B C32B C33B 61.4(12) . . . . ? C3B O31B C32B C33B -178.7(10) . . . . ? O31B C32B C33B C34B -151.7(14) . . . . ? C3B O31B C32D C33D -74.2(9) . . . . ? C32B O31B C32D C33D 1.3(11) . . . . ? O31B C32D C33D C34D 134.5(11) . . . . ? O31B C3B C4B O41B 61.2(3) . . . . ? C2B C3B C4B O41B 179.4(3) . . . . ? O31B C3B C4B C5B -177.9(3) . . . . ? C2B C3B C4B C5B -59.8(3) . . . . ? O41B C4B C5B O51B 62.3(3) . . . . ? C3B C4B C5B O51B -60.9(3) . . . . ? O41B C4B C5B C6B -177.6(2) . . . . ? C3B C4B C5B C6B 59.2(3) . . . . ? O51B C5B C6B O61B -58.8(3) . . . . ? C4B C5B C6B O61B 179.9(2) . . . . ? O51B C5B C6B C1B 65.1(3) . . . . ? C4B C5B C6B C1B -56.1(3) . . . . ? O11B C1B C6B O61B -63.5(3) . . . . ? C2B C1B C6B O61B 176.7(2) . . . . ? O11B C1B C6B C5B 174.0(2) . . . . ? C2B C1B C6B C5B 54.2(3) . . . . ? _diffrn_measured_fraction_theta_max 0.987 _diffrn_reflns_theta_full 28.35 _diffrn_measured_fraction_theta_full 0.987 _refine_diff_density_max 0.518 _refine_diff_density_min -0.427 _refine_diff_density_rms 0.050 _database_code_depnum_ccdc_archive 'CCDC 938830' ####################################################################### # # 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_fro6703 _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C34 H35 Br O10' _chemical_formula_weight 683.53 _chemical_absolute_configuration ad loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 '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 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Br Br -0.2901 2.4595 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M P21 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y+1/2, -z' _cell_length_a 11.9744(2) _cell_length_b 8.0367(2) _cell_length_c 17.1372(3) _cell_angle_alpha 90.00 _cell_angle_beta 108.8580(10) _cell_angle_gamma 90.00 _cell_volume 1560.67(5) _cell_formula_units_Z 2 _cell_measurement_temperature 223(2) _cell_measurement_reflns_used 1922 _cell_measurement_theta_min 4.08 _cell_measurement_theta_max 28.28 _exptl_crystal_description block _exptl_crystal_colour colourless _exptl_crystal_size_max 0.28 _exptl_crystal_size_mid 0.23 _exptl_crystal_size_min 0.23 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.455 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 708 _exptl_absorpt_coefficient_mu 1.376 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.6993 _exptl_absorpt_correction_T_max 0.7426 _exptl_absorpt_process_details 'Denzo (Otwinowski, Borek, Majewski & Minor, 2003)' _exptl_special_details ; ? ; _diffrn_ambient_temperature 223(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'rotating anode Nonius FR591' _diffrn_radiation_monochromator 'Montel mirror' _diffrn_measurement_device_type 'Nonius KappaCCD APEXII' _diffrn_measurement_method '\w and \f scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 8893 _diffrn_reflns_av_R_equivalents 0.021 _diffrn_reflns_av_sigmaI/netI 0.0291 _diffrn_reflns_limit_h_min -14 _diffrn_reflns_limit_h_max 14 _diffrn_reflns_limit_k_min -9 _diffrn_reflns_limit_k_max 8 _diffrn_reflns_limit_l_min -20 _diffrn_reflns_limit_l_max 20 _diffrn_reflns_theta_min 4.35 _diffrn_reflns_theta_max 25.00 _reflns_number_total 4744 _reflns_number_gt 4550 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Collect (Nonius B.V., 1998)' _computing_cell_refinement 'Collect (Nonius B.V., 1998)' _computing_data_reduction 'Denzo-SMN (Otwinowski & Minor, 1997)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'XP (BrukerAXS, 2000)' _computing_publication_material 'SHELXL-97 (Sheldrick, 1997)' _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. The hydrogens at O51 and watter molecule (O71 and O72, O72A) were refined freely, but with O-H distance restraints (SADI). ; _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^)+(0.0000P)^2^+1.2026P] 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 mixed _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881' _refine_ls_abs_structure_Flack -0.014(8) _refine_ls_number_reflns 4744 _refine_ls_number_parameters 439 _refine_ls_number_restraints 18 _refine_ls_R_factor_all 0.0344 _refine_ls_R_factor_gt 0.0315 _refine_ls_wR_factor_ref 0.0708 _refine_ls_wR_factor_gt 0.0681 _refine_ls_goodness_of_fit_ref 1.101 _refine_ls_restrained_S_all 1.341 _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 Br1 Br -0.03942(4) 0.25473(6) 0.02927(2) 0.05302(14) Uani 1 1 d . . . C1 C 0.2577(3) 0.8638(5) 0.4243(2) 0.0286(8) Uani 1 1 d . . . H1 H 0.3054 0.9386 0.4017 0.034 Uiso 1 1 calc R . . C2 C 0.3363(3) 0.7860(4) 0.50428(19) 0.0283(8) Uani 1 1 d . . . H2 H 0.4017 0.7256 0.4933 0.034 Uiso 1 1 calc R . . C3 C 0.3874(3) 0.9226(5) 0.5669(2) 0.0286(8) Uani 1 1 d . . . H3 H 0.4402 0.9949 0.5477 0.034 Uiso 1 1 calc R . . C4 C 0.2905(3) 1.0266(4) 0.5830(2) 0.0285(7) Uani 1 1 d . . . H4 H 0.2464 0.9583 0.6113 0.034 Uiso 1 1 calc R . . C5 C 0.2059(3) 1.0958(4) 0.5024(2) 0.0275(7) Uani 1 1 d . . . H5 H 0.2482 1.1791 0.4799 0.033 Uiso 1 1 calc R . . C6 C 0.1565(3) 0.9612(4) 0.4378(2) 0.0275(7) Uani 1 1 d . . . H6 H 0.1053 0.8852 0.4565 0.033 Uiso 1 1 calc R . . O11 O 0.20427(18) 0.7358(4) 0.36481(13) 0.0330(5) Uani 1 1 d . . . C12 C 0.2629(3) 0.6864(5) 0.3140(2) 0.0332(8) Uani 1 1 d . . . O13 O 0.3612(2) 0.7323(5) 0.32036(16) 0.0527(8) Uani 1 1 d . . . C14 C 0.1897(3) 0.5757(5) 0.2479(2) 0.0307(8) Uani 1 1 d . . . C15 C 0.2216(3) 0.5575(5) 0.1774(2) 0.0356(9) Uani 1 1 d . . . H15 H 0.2901 0.6101 0.1742 0.043 Uiso 1 1 calc R . . C16 C 0.1538(3) 0.4628(5) 0.1119(2) 0.0368(9) Uani 1 1 d . . . H16 H 0.1747 0.4516 0.0638 0.044 Uiso 1 1 calc R . . C17 C 0.0550(3) 0.3853(5) 0.1189(2) 0.0362(9) Uani 1 1 d . . . C18 C 0.0232(3) 0.3960(5) 0.1888(2) 0.0399(9) Uani 1 1 d . . . H18 H -0.0431 0.3382 0.1926 0.048 Uiso 1 1 calc R . . C19 C 0.0908(3) 0.4936(5) 0.2540(2) 0.0385(9) Uani 1 1 d . . . H19 H 0.0696 0.5040 0.3020 0.046 Uiso 1 1 calc R . . O21 O 0.2692(2) 0.6718(3) 0.53414(16) 0.0357(6) Uani 1 1 d . . . H21 H 0.3115 0.5920 0.5565 0.054 Uiso 1 1 calc R . . O31 O 0.4519(2) 0.8488(3) 0.64545(14) 0.0328(6) Uani 1 1 d . . . C32 C 0.5613(3) 0.7916(5) 0.6555(2) 0.0333(9) Uani 1 1 d . . . O33 O 0.6091(2) 0.8037(4) 0.60384(15) 0.0454(8) Uani 1 1 d . . . C34 C 0.6136(3) 0.7124(4) 0.7376(2) 0.0319(9) Uani 1 1 d . . . C35 C 0.7203(3) 0.6288(5) 0.7537(2) 0.0378(9) Uani 1 1 d . . . H35 H 0.7586 0.6253 0.7137 0.045 Uiso 1 1 calc R . . C36 C 0.7701(4) 0.5505(6) 0.8294(3) 0.0470(11) Uani 1 1 d . . . H36 H 0.8412 0.4914 0.8402 0.056 Uiso 1 1 calc R . . C37 C 0.7152(4) 0.5594(6) 0.8886(3) 0.0539(12) Uani 1 1 d . . . H37 H 0.7491 0.5062 0.9397 0.065 Uiso 1 1 calc R . . C38 C 0.6113(4) 0.6457(7) 0.8735(3) 0.0536(12) Uani 1 1 d . . . H38 H 0.5755 0.6535 0.9148 0.064 Uiso 1 1 calc R . . C39 C 0.5589(3) 0.7211(6) 0.7980(2) 0.0431(11) Uani 1 1 d . . . H39 H 0.4869 0.7780 0.7874 0.052 Uiso 1 1 calc R . . O41 O 0.3478(2) 1.1617(4) 0.63478(15) 0.0401(6) Uani 1 1 d . . . C42 C 0.2952(4) 1.2178(6) 0.6941(2) 0.0528(12) Uani 1 1 d . . . H42A H 0.2109 1.1907 0.6745 0.063 Uiso 1 1 calc R . . H42B H 0.3028 1.3390 0.6992 0.063 Uiso 1 1 calc R . . C43 C 0.3514(3) 1.1399(6) 0.7780(2) 0.0419(10) Uani 1 1 d . . . C44 C 0.4660(4) 1.1808(7) 0.8240(3) 0.0538(12) Uani 1 1 d . . . H44 H 0.5099 1.2535 0.8023 0.065 Uiso 1 1 calc R . . C45 C 0.5163(4) 1.1142(7) 0.9026(3) 0.0609(14) Uani 1 1 d . . . H45 H 0.5939 1.1430 0.9340 0.073 Uiso 1 1 calc R . . C46 C 0.4528(5) 1.0063(7) 0.9346(3) 0.0593(13) Uani 1 1 d . . . H46 H 0.4869 0.9605 0.9875 0.071 Uiso 1 1 calc R . . C47 C 0.3402(5) 0.9669(7) 0.8887(3) 0.0648(14) Uani 1 1 d . . . H47 H 0.2963 0.8938 0.9103 0.078 Uiso 1 1 calc R . . C48 C 0.2890(4) 1.0334(7) 0.8103(3) 0.0549(12) Uani 1 1 d . . . H48 H 0.2111 1.0049 0.7794 0.066 Uiso 1 1 calc R . . O51 O 0.1110(2) 1.1763(4) 0.52093(16) 0.0331(6) Uani 1 1 d . . . H05 H 0.096(4) 1.267(7) 0.497(3) 0.057(15) Uiso 1 1 d . . . O61 O 0.0911(2) 1.0329(3) 0.36069(15) 0.0352(6) Uani 1 1 d . . . C62 C -0.0318(3) 1.0558(6) 0.3454(2) 0.0432(10) Uani 1 1 d . . . H62A H -0.0473 1.1721 0.3558 0.052 Uiso 1 1 calc R . . H62B H -0.0578 0.9856 0.3831 0.052 Uiso 1 1 calc R . . C63 C -0.1002(3) 1.0112(5) 0.2578(2) 0.0359(9) Uani 1 1 d . . . C64 C -0.0587(4) 0.8969(6) 0.2141(2) 0.0453(10) Uani 1 1 d . . . H64 H 0.0165 0.8501 0.2382 0.054 Uiso 1 1 calc R . . C65 C -0.1261(4) 0.8492(7) 0.1349(2) 0.0513(11) Uani 1 1 d . . . H65 H -0.0964 0.7712 0.1058 0.062 Uiso 1 1 calc R . . C66 C -0.2365(4) 0.9167(7) 0.0993(3) 0.0542(12) Uani 1 1 d . . . H66 H -0.2829 0.8844 0.0459 0.065 Uiso 1 1 calc R . . C67 C -0.2784(4) 1.0313(6) 0.1420(3) 0.0516(12) Uani 1 1 d . . . H67 H -0.3538 1.0775 0.1176 0.062 Uiso 1 1 calc R . . C68 C -0.2111(3) 1.0802(6) 0.2211(3) 0.0434(10) Uani 1 1 d . . . H68 H -0.2406 1.1598 0.2496 0.052 Uiso 1 1 calc R . . O71 O 0.0645(2) 0.4794(4) 0.44911(19) 0.0412(7) Uani 1 1 d D . . H71A H 0.121(3) 0.524(6) 0.465(3) 0.062 Uiso 1 1 d D . . H71B H 0.016(3) 0.526(6) 0.457(3) 0.062 Uiso 1 1 d D . . O72 O 0.4363(9) 0.4361(10) 0.5595(10) 0.045(3) Uani 0.67(5) 1 d PD A 1 H72A H 0.429(6) 0.366(9) 0.583(7) 0.068 Uiso 0.67(5) 1 d PD A 1 H72B H 0.426(7) 0.392(11) 0.522(3) 0.068 Uiso 0.67(5) 1 d PD A 1 O72A O 0.437(2) 0.445(3) 0.606(5) 0.092(15) Uani 0.33(5) 1 d PD A 2 H72C H 0.396(13) 0.388(18) 0.613(11) 0.138 Uiso 0.33(5) 1 d PD A 2 H72D H 0.471(14) 0.376(14) 0.627(10) 0.138 Uiso 0.33(5) 1 d PD A 2 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 Br1 0.0551(2) 0.0508(3) 0.0422(2) -0.0124(2) 0.00059(16) -0.0062(2) C1 0.0284(18) 0.030(2) 0.0281(17) -0.0045(15) 0.0102(14) -0.0036(14) C2 0.0268(15) 0.026(2) 0.0319(16) -0.0011(15) 0.0101(13) 0.0023(14) C3 0.0264(17) 0.032(2) 0.0258(17) 0.0024(16) 0.0068(14) 0.0026(15) C4 0.0281(17) 0.0265(19) 0.0316(18) -0.0006(16) 0.0105(14) 0.0016(14) C5 0.0237(16) 0.0261(19) 0.0341(18) 0.0014(15) 0.0112(14) 0.0043(14) C6 0.0263(17) 0.0271(19) 0.0276(17) 0.0007(15) 0.0068(14) 0.0000(14) O11 0.0309(11) 0.0368(15) 0.0321(11) -0.0080(13) 0.0111(9) -0.0045(12) C12 0.0310(18) 0.035(2) 0.0334(18) -0.0032(16) 0.0106(15) 0.0029(15) O13 0.0344(13) 0.069(2) 0.0591(16) -0.0275(18) 0.0210(12) -0.0128(16) C14 0.0339(18) 0.028(2) 0.0308(18) -0.0014(15) 0.0109(15) 0.0029(15) C15 0.0361(19) 0.037(2) 0.0356(19) 0.0001(18) 0.0145(16) -0.0017(17) C16 0.048(2) 0.036(2) 0.0281(18) 0.0033(17) 0.0144(17) 0.0040(17) C17 0.043(2) 0.029(2) 0.0305(18) -0.0016(16) 0.0037(16) 0.0022(16) C18 0.037(2) 0.037(2) 0.045(2) -0.0073(19) 0.0124(17) -0.0049(17) C19 0.042(2) 0.038(2) 0.038(2) -0.0058(18) 0.0163(17) -0.0022(17) O21 0.0341(13) 0.0281(14) 0.0444(14) 0.0070(12) 0.0119(11) 0.0013(11) O31 0.0287(13) 0.0394(15) 0.0284(12) 0.0030(11) 0.0066(10) 0.0081(11) C32 0.0256(16) 0.036(2) 0.0356(17) -0.0045(16) 0.0056(14) 0.0011(14) O33 0.0318(13) 0.071(2) 0.0346(13) 0.0040(14) 0.0125(11) 0.0099(13) C34 0.0266(16) 0.033(2) 0.0318(16) -0.0008(15) 0.0040(13) -0.0009(14) C35 0.0316(19) 0.038(2) 0.039(2) -0.0086(18) 0.0037(16) 0.0004(16) C36 0.041(2) 0.039(3) 0.049(3) -0.004(2) -0.0018(19) 0.0069(19) C37 0.046(2) 0.059(3) 0.046(2) 0.016(2) 0.000(2) 0.000(2) C38 0.043(2) 0.076(3) 0.041(2) 0.018(2) 0.0131(19) 0.002(2) C39 0.0304(18) 0.054(3) 0.0426(19) 0.007(2) 0.0093(15) 0.0024(18) O41 0.0421(15) 0.0400(15) 0.0350(13) -0.0119(13) 0.0078(11) 0.0028(12) C42 0.062(3) 0.051(3) 0.041(2) -0.010(2) 0.0119(19) 0.022(2) C43 0.042(2) 0.047(3) 0.0346(19) -0.0135(19) 0.0099(17) 0.0089(18) C44 0.046(2) 0.072(3) 0.044(2) -0.002(2) 0.0150(19) 0.003(2) C45 0.046(3) 0.090(4) 0.041(2) -0.010(3) 0.005(2) 0.006(3) C46 0.070(3) 0.070(3) 0.038(2) 0.000(2) 0.018(2) 0.018(3) C47 0.083(4) 0.056(3) 0.067(3) -0.004(3) 0.041(3) -0.005(3) C48 0.047(2) 0.063(3) 0.053(3) -0.014(2) 0.015(2) -0.002(2) O51 0.0299(13) 0.0291(14) 0.0423(15) 0.0043(13) 0.0144(11) 0.0065(11) O61 0.0233(12) 0.0474(17) 0.0308(13) 0.0089(12) 0.0031(10) 0.0031(11) C62 0.0289(18) 0.058(3) 0.039(2) 0.002(2) 0.0061(16) 0.0109(18) C63 0.0267(18) 0.042(2) 0.0359(19) 0.0095(18) 0.0056(15) -0.0038(16) C64 0.036(2) 0.052(3) 0.044(2) 0.004(2) 0.0087(18) 0.0061(19) C65 0.051(3) 0.063(3) 0.037(2) -0.006(2) 0.0112(19) -0.004(2) C66 0.045(2) 0.071(3) 0.037(2) 0.010(2) 0.0011(19) -0.014(2) C67 0.032(2) 0.059(3) 0.051(3) 0.015(2) -0.0038(19) -0.001(2) C68 0.034(2) 0.043(2) 0.049(2) 0.010(2) 0.0074(18) 0.0009(18) O71 0.0388(16) 0.0332(17) 0.0565(18) 0.0001(14) 0.0221(15) 0.0005(12) O72 0.057(4) 0.033(3) 0.049(6) 0.010(3) 0.022(4) 0.012(2) O72A 0.070(9) 0.045(9) 0.13(4) 0.019(13) -0.015(13) 0.013(7) _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 Br1 C17 1.902(4) . ? C1 O11 1.445(4) . ? C1 C6 1.522(5) . ? C1 C2 1.523(5) . ? C1 H1 0.9900 . ? C2 O21 1.420(4) . ? C2 C3 1.519(5) . ? C2 H2 0.9900 . ? C3 O31 1.446(4) . ? C3 C4 1.526(5) . ? C3 H3 0.9900 . ? C4 O41 1.430(4) . ? C4 C5 1.530(5) . ? C4 H4 0.9900 . ? C5 O51 1.430(4) . ? C5 C6 1.523(5) . ? C5 H5 0.9900 . ? C6 O61 1.422(4) . ? C6 H6 0.9900 . ? O11 C12 1.342(4) . ? C12 O13 1.204(4) . ? C12 C14 1.484(5) . ? C14 C15 1.387(5) . ? C14 C19 1.390(5) . ? C15 C16 1.381(5) . ? C15 H15 0.9400 . ? C16 C17 1.377(5) . ? C16 H16 0.9400 . ? C17 C18 1.371(5) . ? C18 C19 1.390(5) . ? C18 H18 0.9400 . ? C19 H19 0.9400 . ? O21 H21 0.8300 . ? O31 C32 1.346(4) . ? C32 O33 1.203(4) . ? C32 C34 1.486(5) . ? C34 C35 1.389(5) . ? C34 C39 1.394(5) . ? C35 C36 1.391(6) . ? C35 H35 0.9400 . ? C36 C37 1.377(6) . ? C36 H36 0.9400 . ? C37 C38 1.374(6) . ? C37 H37 0.9400 . ? C38 C39 1.383(5) . ? C38 H38 0.9400 . ? C39 H39 0.9400 . ? O41 C42 1.431(4) . ? C42 C43 1.511(5) . ? C42 H42A 0.9800 . ? C42 H42B 0.9800 . ? C43 C48 1.366(7) . ? C43 C44 1.383(6) . ? C44 C45 1.393(6) . ? C44 H44 0.9400 . ? C45 C46 1.378(7) . ? C45 H45 0.9400 . ? C46 C47 1.361(7) . ? C46 H46 0.9400 . ? C47 C48 1.391(7) . ? C47 H47 0.9400 . ? C48 H48 0.9400 . ? O51 H05 0.82(6) . ? O61 C62 1.421(4) . ? C62 C63 1.503(5) . ? C62 H62A 0.9800 . ? C62 H62B 0.9800 . ? C63 C64 1.375(6) . ? C63 C68 1.388(5) . ? C64 C65 1.390(6) . ? C64 H64 0.9400 . ? C65 C66 1.376(6) . ? C65 H65 0.9400 . ? C66 C67 1.369(7) . ? C66 H66 0.9400 . ? C67 C68 1.391(6) . ? C67 H67 0.9400 . ? C68 H68 0.9400 . ? O71 H71A 0.736(16) . ? O71 H71B 0.738(16) . ? O72 H72A 0.712(17) . ? O72 H72B 0.713(17) . ? O72 H72C 1.22(11) . ? O72 H72D 1.19(12) . ? O72A H72A 0.73(11) . ? O72A H72B 1.47(7) . ? O72A H72C 0.707(17) . ? O72A H72D 0.706(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 O11 C1 C6 106.3(3) . . ? O11 C1 C2 110.3(3) . . ? C6 C1 C2 111.4(3) . . ? O11 C1 H1 109.6 . . ? C6 C1 H1 109.6 . . ? C2 C1 H1 109.6 . . ? O21 C2 C3 111.0(3) . . ? O21 C2 C1 109.4(3) . . ? C3 C2 C1 109.2(3) . . ? O21 C2 H2 109.1 . . ? C3 C2 H2 109.1 . . ? C1 C2 H2 109.1 . . ? O31 C3 C2 109.5(3) . . ? O31 C3 C4 105.4(3) . . ? C2 C3 C4 111.6(3) . . ? O31 C3 H3 110.1 . . ? C2 C3 H3 110.1 . . ? C4 C3 H3 110.1 . . ? O41 C4 C3 106.7(3) . . ? O41 C4 C5 109.2(3) . . ? C3 C4 C5 110.9(3) . . ? O41 C4 H4 110.0 . . ? C3 C4 H4 110.0 . . ? C5 C4 H4 110.0 . . ? O51 C5 C6 109.5(3) . . ? O51 C5 C4 107.8(3) . . ? C6 C5 C4 112.7(3) . . ? O51 C5 H5 108.9 . . ? C6 C5 H5 108.9 . . ? C4 C5 H5 108.9 . . ? O61 C6 C1 107.1(3) . . ? O61 C6 C5 110.8(3) . . ? C1 C6 C5 109.5(3) . . ? O61 C6 H6 109.8 . . ? C1 C6 H6 109.8 . . ? C5 C6 H6 109.8 . . ? C12 O11 C1 117.6(3) . . ? O13 C12 O11 123.5(3) . . ? O13 C12 C14 124.8(3) . . ? O11 C12 C14 111.7(3) . . ? C15 C14 C19 119.8(3) . . ? C15 C14 C12 117.9(3) . . ? C19 C14 C12 122.3(3) . . ? C16 C15 C14 120.7(3) . . ? C16 C15 H15 119.7 . . ? C14 C15 H15 119.7 . . ? C17 C16 C15 118.3(3) . . ? C17 C16 H16 120.8 . . ? C15 C16 H16 120.8 . . ? C18 C17 C16 122.4(3) . . ? C18 C17 Br1 118.7(3) . . ? C16 C17 Br1 118.9(3) . . ? C17 C18 C19 118.9(4) . . ? C17 C18 H18 120.6 . . ? C19 C18 H18 120.6 . . ? C14 C19 C18 119.8(4) . . ? C14 C19 H19 120.1 . . ? C18 C19 H19 120.1 . . ? C2 O21 H21 109.5 . . ? C32 O31 C3 117.7(3) . . ? O33 C32 O31 123.6(3) . . ? O33 C32 C34 125.2(3) . . ? O31 C32 C34 111.2(3) . . ? C35 C34 C39 119.9(3) . . ? C35 C34 C32 118.3(3) . . ? C39 C34 C32 121.7(3) . . ? C34 C35 C36 119.6(4) . . ? C34 C35 H35 120.2 . . ? C36 C35 H35 120.2 . . ? C37 C36 C35 120.0(4) . . ? C37 C36 H36 120.0 . . ? C35 C36 H36 120.0 . . ? C38 C37 C36 120.4(4) . . ? C38 C37 H37 119.8 . . ? C36 C37 H37 119.8 . . ? C37 C38 C39 120.4(4) . . ? C37 C38 H38 119.8 . . ? C39 C38 H38 119.8 . . ? C38 C39 C34 119.6(4) . . ? C38 C39 H39 120.2 . . ? C34 C39 H39 120.2 . . ? C4 O41 C42 116.5(3) . . ? O41 C42 C43 112.5(3) . . ? O41 C42 H42A 109.1 . . ? C43 C42 H42A 109.1 . . ? O41 C42 H42B 109.1 . . ? C43 C42 H42B 109.1 . . ? H42A C42 H42B 107.8 . . ? C48 C43 C44 119.3(4) . . ? C48 C43 C42 120.7(4) . . ? C44 C43 C42 119.9(4) . . ? C43 C44 C45 120.0(5) . . ? C43 C44 H44 120.0 . . ? C45 C44 H44 120.0 . . ? C46 C45 C44 120.3(4) . . ? C46 C45 H45 119.8 . . ? C44 C45 H45 119.8 . . ? C47 C46 C45 119.2(4) . . ? C47 C46 H46 120.4 . . ? C45 C46 H46 120.4 . . ? C46 C47 C48 120.9(5) . . ? C46 C47 H47 119.5 . . ? C48 C47 H47 119.5 . . ? C43 C48 C47 120.3(5) . . ? C43 C48 H48 119.9 . . ? C47 C48 H48 119.9 . . ? C5 O51 H05 111(3) . . ? C62 O61 C6 116.7(3) . . ? O61 C62 C63 110.5(3) . . ? O61 C62 H62A 109.6 . . ? C63 C62 H62A 109.6 . . ? O61 C62 H62B 109.6 . . ? C63 C62 H62B 109.6 . . ? H62A C62 H62B 108.1 . . ? C64 C63 C68 118.7(4) . . ? C64 C63 C62 121.9(3) . . ? C68 C63 C62 119.3(4) . . ? C63 C64 C65 121.2(4) . . ? C63 C64 H64 119.4 . . ? C65 C64 H64 119.4 . . ? C66 C65 C64 119.7(5) . . ? C66 C65 H65 120.2 . . ? C64 C65 H65 120.2 . . ? C67 C66 C65 119.6(4) . . ? C67 C66 H66 120.2 . . ? C65 C66 H66 120.2 . . ? C66 C67 C68 120.9(4) . . ? C66 C67 H67 119.5 . . ? C68 C67 H67 119.5 . . ? C63 C68 C67 119.8(4) . . ? C63 C68 H68 120.1 . . ? C67 C68 H68 120.1 . . ? H71A O71 H71B 111(6) . . ? H72A O72 H72B 96(10) . . ? H72A O72 H72C 35(10) . . ? H72B O72 H72C 121(10) . . ? H72A O72 H72D 37(10) . . ? H72B O72 H72D 125(10) . . ? H72C O72 H72D 41(10) . . ? H72A O72A H72B 43(6) . . ? H72A O72A H72C 63(10) . . ? H72B O72A H72C 97(10) . . ? H72A O72A H72D 63(10) . . ? H72B O72A H72D 97(10) . . ? H72C O72A H72D 74(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 O11 C1 C2 O21 -56.0(3) . . . . ? C6 C1 C2 O21 61.8(4) . . . . ? O11 C1 C2 C3 -177.7(3) . . . . ? C6 C1 C2 C3 -59.9(4) . . . . ? O21 C2 C3 O31 53.3(3) . . . . ? C1 C2 C3 O31 174.1(3) . . . . ? O21 C2 C3 C4 -62.9(4) . . . . ? C1 C2 C3 C4 57.8(4) . . . . ? O31 C3 C4 O41 67.9(3) . . . . ? C2 C3 C4 O41 -173.4(3) . . . . ? O31 C3 C4 C5 -173.3(3) . . . . ? C2 C3 C4 C5 -54.5(4) . . . . ? O41 C4 C5 O51 -68.7(3) . . . . ? C3 C4 C5 O51 173.9(3) . . . . ? O41 C4 C5 C6 170.4(3) . . . . ? C3 C4 C5 C6 53.0(4) . . . . ? O11 C1 C6 O61 -61.7(3) . . . . ? C2 C1 C6 O61 178.2(3) . . . . ? O11 C1 C6 C5 178.1(3) . . . . ? C2 C1 C6 C5 57.9(4) . . . . ? O51 C5 C6 O61 67.8(3) . . . . ? C4 C5 C6 O61 -172.3(3) . . . . ? O51 C5 C6 C1 -174.3(3) . . . . ? C4 C5 C6 C1 -54.4(4) . . . . ? C6 C1 O11 C12 149.0(3) . . . . ? C2 C1 O11 C12 -90.1(3) . . . . ? C1 O11 C12 O13 6.8(6) . . . . ? C1 O11 C12 C14 -170.7(3) . . . . ? O13 C12 C14 C15 -17.4(6) . . . . ? O11 C12 C14 C15 160.0(3) . . . . ? O13 C12 C14 C19 163.6(4) . . . . ? O11 C12 C14 C19 -18.9(5) . . . . ? C19 C14 C15 C16 2.2(6) . . . . ? C12 C14 C15 C16 -176.8(4) . . . . ? C14 C15 C16 C17 -0.9(6) . . . . ? C15 C16 C17 C18 -1.4(6) . . . . ? C15 C16 C17 Br1 179.9(3) . . . . ? C16 C17 C18 C19 2.4(6) . . . . ? Br1 C17 C18 C19 -178.9(3) . . . . ? C15 C14 C19 C18 -1.1(6) . . . . ? C12 C14 C19 C18 177.8(4) . . . . ? C17 C18 C19 C14 -1.1(6) . . . . ? C2 C3 O31 C32 79.0(4) . . . . ? C4 C3 O31 C32 -160.8(3) . . . . ? C3 O31 C32 O33 2.6(5) . . . . ? C3 O31 C32 C34 -177.2(3) . . . . ? O33 C32 C34 C35 -7.6(6) . . . . ? O31 C32 C34 C35 172.2(3) . . . . ? O33 C32 C34 C39 172.0(4) . . . . ? O31 C32 C34 C39 -8.2(5) . . . . ? C39 C34 C35 C36 1.8(6) . . . . ? C32 C34 C35 C36 -178.6(4) . . . . ? C34 C35 C36 C37 -1.6(6) . . . . ? C35 C36 C37 C38 -0.1(7) . . . . ? C36 C37 C38 C39 1.6(8) . . . . ? C37 C38 C39 C34 -1.4(7) . . . . ? C35 C34 C39 C38 -0.3(6) . . . . ? C32 C34 C39 C38 -179.9(4) . . . . ? C3 C4 O41 C42 -145.7(3) . . . . ? C5 C4 O41 C42 94.4(3) . . . . ? C4 O41 C42 C43 95.7(4) . . . . ? O41 C42 C43 C48 -113.8(5) . . . . ? O41 C42 C43 C44 68.5(5) . . . . ? C48 C43 C44 C45 -0.3(7) . . . . ? C42 C43 C44 C45 177.5(4) . . . . ? C43 C44 C45 C46 0.6(7) . . . . ? C44 C45 C46 C47 -0.6(8) . . . . ? C45 C46 C47 C48 0.3(8) . . . . ? C44 C43 C48 C47 0.0(7) . . . . ? C42 C43 C48 C47 -177.7(4) . . . . ? C46 C47 C48 C43 0.0(8) . . . . ? C1 C6 O61 C62 149.4(3) . . . . ? C5 C6 O61 C62 -91.2(4) . . . . ? C6 O61 C62 C63 -139.2(3) . . . . ? O61 C62 C63 C64 27.6(6) . . . . ? O61 C62 C63 C68 -155.9(3) . . . . ? C68 C63 C64 C65 -0.5(6) . . . . ? C62 C63 C64 C65 176.0(4) . . . . ? C63 C64 C65 C66 -0.2(7) . . . . ? C64 C65 C66 C67 0.6(7) . . . . ? C65 C66 C67 C68 -0.2(7) . . . . ? C64 C63 C68 C67 0.9(6) . . . . ? C62 C63 C68 C67 -175.6(4) . . . . ? C66 C67 C68 C63 -0.6(7) . . . . ? loop_ _geom_hbond_atom_site_label_D _geom_hbond_atom_site_label_H _geom_hbond_atom_site_label_A _geom_hbond_distance_DH _geom_hbond_distance_HA _geom_hbond_distance_DA _geom_hbond_angle_DHA _geom_hbond_site_symmetry_A O71 H71A O21 0.736(16) 2.14(2) 2.866(4) 167(6) . O51 H05 O71 0.82(6) 1.89(6) 2.704(4) 177(4) 1_565 O71 H71B O51 0.738(16) 2.071(17) 2.807(4) 175(6) 2_546 _diffrn_measured_fraction_theta_max 0.987 _diffrn_reflns_theta_full 25.00 _diffrn_measured_fraction_theta_full 0.987 _refine_diff_density_max 0.177 _refine_diff_density_min -0.215 _refine_diff_density_rms 0.038 _database_code_depnum_ccdc_archive 'CCDC 938831'