data_bra_dmso_1 # SUBMISSION DETAILS _publ_contact_author_name 'Doris E. Braun' _publ_contact_author_address ; Department of Chemistry University College London 20 Gordon Street London WC1H 0AJ United Kingdom ; _publ_contact_author_phone '44 (0)20 7679 4622' _publ_contact_author_fax '44 (0)20 7679 7463' _publ_contact_author_email 's.l.price@ucl.ac.uk' _publ_requested_journal 'Crystal Growth & Design' # TITLE AND AUTHOR LIST _publ_section_title ; Solid state forms of beta-Resorcylic Acid: How Exhaustive should a Polymorph Screen be? ; loop_ _publ_author_name _publ_author_address 'Doris E. Braun' ; Department of Chemistry University College London 20 Gordon Street London WC1H 0AJ United Kingdom ; 'Panagiotis G.Karamertzanis' ; Centre for Process Systems Engineering Department of chemical Engineering Imperial College London Lodon SW7 2AZ United Kingdom ; 'Jean-Baptiste Arlin' ; University of Strathclyde Strathclyde Institute of Pharmacy and Biomedical Sciences 27 Taylor Street Glasgow G4 0NR United Kingdom ; 'Alastair J. Florence' ; University of Strathclyde Strathclyde Institute of Pharmacy and Biomedical Sciences 27 Taylor Street Glasgow G4 0NR United Kingdom ; 'Volker Kahlenberg' ; Institute of Mineralogy and Petrography University of Innsbruck Innrain 52 6020 Innsbruck Austria ; 'Derek A. Tocher' ; Department of Chemistry University College London 20 Gordon Street London WC1H 0AJ United Kingdom ; 'Ulrich J. Griesser' ; Institute of Pharmacy University of Innsbruck Innrain 52 6020 Innsbruck Austria ; 'Sarah L. Price' ; Department of Chemistry University College London 20 Gordon Street London WC1H 0AJ United Kingdom ; #\#CIF_1.1 # CIF produced by WinGX routine CIF_UPDATE # Created on 2010-05-27 at 10:39:19 # Using CIFtbx version 2.6.2 16 Jun 1998 # Dictionary name : cif_core.dic # Dictionary vers : 2.3 # Request file : c:\wingx\files\archive.dat # CIF files read : bra_dmso_1 bra_dmso_archive _audit_creation_date 2010-05-27T10:39:19-00:00 _audit_creation_method 'WinGX routine CIF_UPDATE' _audit_conform_dict_name cif_core.dic _audit_conform_dict_version 2.3 _audit_conform_dict_location ftp://ftp.iucr.org/pub/cif_core.dic _publ_requested_category FO #----------------------------------------------------------------------------# # CHEMICAL INFORMATION # #----------------------------------------------------------------------------# _chemical_name_systematic '2,4-hidyroxybenzoic acid DMSO hemisolvate' _chemical_name_common 'beta resoryclic DMSO hemisolvate' _chemical_formula_moiety '2(C7 H6 O4), C2 H6 O S' _chemical_formula_sum 'C16 H18 O9 S' _chemical_formula_weight 386.36 #----------------------------------------------------------------------------# # UNIT CELL INFORMATION # #----------------------------------------------------------------------------# _symmetry_cell_setting orthorhombic _symmetry_space_group_name_H-M 'P 21 21 21' _symmetry_space_group_name_Hall 'P 2ac 2ab' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, -y, z+1/2' 'x+1/2, -y+1/2, -z' '-x, y+1/2, -z+1/2' _cell_length_a 6.39832(12) _cell_length_b 11.7099(3) _cell_length_c 23.2362(5) _cell_angle_alpha 90 _cell_angle_beta 90 _cell_angle_gamma 90 _cell_volume 1740.94(7) _cell_formula_units_Z 4 _cell_measurement_temperature 173(2) _cell_measurement_reflns_used 6563 _cell_measurement_theta_min 3.1494 _cell_measurement_theta_max 28.464 #----------------------------------------------------------------------------# # CRYSTAL INFORMATION # #----------------------------------------------------------------------------# _exptl_crystal_description fragment _exptl_crystal_colour colourless _exptl_crystal_size_max 0.4 _exptl_crystal_size_mid 0.32 _exptl_crystal_size_min 0.3 _exptl_crystal_density_diffrn 1.474 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 808 _exptl_special_details ; ? ; #----------------------------------------------------------------------------# # ABSORPTION CORRECTION # #----------------------------------------------------------------------------# _exptl_absorpt_coefficient_mu 0.234 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details ; CrysAlis RED, Oxford Diffraction Ltd., Version 1.171.32.24 (release 21-04-2008 CrysAlis171 .NET) (compiled Apr 21 2008,18:23:10) Empirical absorption correction using spherical harmonics, implemented in SCALE3 ABSPACK scaling algorithm. ; _exptl_absorpt_correction_T_min 0.8779 _exptl_absorpt_correction_T_max 0.93 #----------------------------------------------------------------------------# # DATA COLLECTION # #----------------------------------------------------------------------------# _diffrn_ambient_temperature 173(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_monochromator graphite _diffrn_detector_area_resol_mean 10.3822 _diffrn_orient_matrix_ub_11 -0.0082428086 _diffrn_orient_matrix_ub_12 0.0194012496 _diffrn_orient_matrix_ub_13 -0.0288132714 _diffrn_orient_matrix_ub_21 -0.0061561137 _diffrn_orient_matrix_ub_22 -0.0573519272 _diffrn_orient_matrix_ub_23 -0.009657181 _diffrn_orient_matrix_ub_31 -0.110402888 _diffrn_orient_matrix_ub_32 0.0017515071 _diffrn_orient_matrix_ub_33 0.0026989795 _diffrn_measurement_device_type 'Oxford diffraction GEMINI R ULTRA' _diffrn_measurement_method '\w scans' _diffrn_reflns_av_R_equivalents 0.032 _diffrn_reflns_av_unetI/netI 0.0337 _diffrn_reflns_number 11590 _diffrn_reflns_limit_h_min -7 _diffrn_reflns_limit_h_max 7 _diffrn_reflns_limit_k_min -12 _diffrn_reflns_limit_k_max 14 _diffrn_reflns_limit_l_min -28 _diffrn_reflns_limit_l_max 23 _diffrn_reflns_theta_min 3.15 _diffrn_reflns_theta_max 25.99 _diffrn_reflns_theta_full 25.99 _diffrn_measured_fraction_theta_full 0.996 _diffrn_measured_fraction_theta_max 0.996 _reflns_number_total 3400 _reflns_number_gt 3014 _reflns_threshold_expression >2sigma(I) #----------------------------------------------------------------------------# # COMPUTER PROGRAMS USED # #----------------------------------------------------------------------------# _computing_data_collection ; CrysAlis CCD, Oxford Diffraction Ltd., Version 1.171.32.24 (release 21-04-2008 CrysAlis171 .NET) (compiled Apr 21 2008,18:23:10) ; _computing_cell_refinement ; CrysAlis RED, Oxford Diffraction Ltd., Version 1.171.32.24 (release 21-04-2008 CrysAlis171 .NET) (compiled Apr 21 2008,18:23:10) ; _computing_data_reduction ; CrysAlis RED, Oxford Diffraction Ltd., Version 1.171.32.24 (release 21-04-2008 CrysAlis171 .NET) (compiled Apr 21 2008,18:23:10) ; _computing_structure_solution 'SIR2002 (Burla et al., 2002)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' #----------------------------------------------------------------------------# # REFINEMENT INFORMATION # #----------------------------------------------------------------------------# _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 distance between O8 and H9 was restrained with DFIX 0.82in SHELXL with a standard uncertainty of 0.02. PLAT094_ALERT_2_C Ratio of Maximum / Minimum Residual Density 2.59: Largest diff. peak and hole in proximity to solvent molecule. ; _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^)+(0.0574P)^2^+0.0000P] 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_number_reflns 3400 _refine_ls_number_parameters 261 _refine_ls_number_restraints 1 _refine_ls_R_factor_all 0.0431 _refine_ls_R_factor_gt 0.0367 _refine_ls_wR_factor_ref 0.0887 _refine_ls_wR_factor_gt 0.0863 _refine_ls_goodness_of_fit_ref 1.019 _refine_ls_restrained_S_all 1.02 _refine_ls_shift/su_max 0.004 _refine_ls_shift/su_mean 0 _refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881' _refine_ls_abs_structure_Flack 0.15(9) _refine_diff_density_max 0.617 _refine_diff_density_min -0.238 _refine_diff_density_rms 0.047 #----------------------------------------------------------------------------# # ATOMIC TYPES, COORDINATES AND THERMAL PARAMETERS # #----------------------------------------------------------------------------# 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 0 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.006 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' S S 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 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 S S 0.38657(9) 0.21771(5) 0.21540(2) 0.02708(15) Uani 1 1 d . . . O6 O -0.0974(2) 0.08137(13) 0.54965(6) 0.0262(3) Uani 1 1 d . . . O1 O 0.5618(3) 0.10327(15) 0.48694(7) 0.0306(4) Uani 1 1 d . . . H1 H 0.661(4) 0.098(2) 0.5037(11) 0.032(8) Uiso 1 1 d . . . O2 O 0.6280(2) -0.07940(13) 0.46424(7) 0.0261(3) Uani 1 1 d . . . O7 O 0.1333(3) 0.19090(13) 0.62063(7) 0.0321(4) Uani 1 1 d . . . H8 H 0.007(5) 0.177(3) 0.5971(15) 0.069(10) Uiso 1 1 d . . . O8 O 0.7634(3) 0.01569(15) 0.68062(8) 0.0310(4) Uani 1 1 d D . . H9 H 0.765(4) 0.0697(18) 0.7003(11) 0.040(9) Uiso 1 1 d D . . O4 O -0.2364(2) 0.00919(15) 0.33674(7) 0.0310(4) Uani 1 1 d . . . H3 H -0.246(5) -0.050(3) 0.3149(15) 0.063(10) Uiso 1 1 d . . . O3 O 0.3771(3) -0.18466(13) 0.39426(7) 0.0344(4) Uani 1 1 d . . . H2 H 0.502(5) -0.174(3) 0.4180(14) 0.065(10) Uiso 1 1 d . . . O5 O -0.0184(3) -0.09814(14) 0.52557(7) 0.0281(4) Uani 1 1 d . . . H7 H -0.133(4) -0.091(2) 0.5063(11) 0.031(7) Uiso 1 1 d . . . C7 C 0.5149(3) 0.0071(2) 0.46070(9) 0.0223(5) Uani 1 1 d . . . C4 C -0.0543(3) 0.0056(2) 0.36668(9) 0.0225(5) Uani 1 1 d . . . C8 C 0.2120(3) -0.00013(19) 0.58709(9) 0.0230(5) Uani 1 1 d . . . O9 O 0.2728(2) 0.32576(14) 0.23435(7) 0.0359(4) Uani 1 1 d . . . C13 C 0.3561(3) -0.09039(19) 0.58757(9) 0.0247(5) Uani 1 1 d . . . H12 H 0.3265 -0.1573 0.5659 0.03 Uiso 1 1 calc R . . C12 C 0.5382(3) -0.08471(19) 0.61833(10) 0.0255(5) Uani 1 1 d . . . H11 H 0.6345 -0.1465 0.6176 0.031 Uiso 1 1 calc R . . C14 C 0.0213(3) -0.0023(2) 0.55295(9) 0.0223(5) Uani 1 1 d . . . C2 C 0.2596(3) -0.08897(18) 0.39675(9) 0.0222(5) Uani 1 1 d . . . C9 C 0.2598(3) 0.09835(18) 0.61950(9) 0.0218(4) Uani 1 1 d . . . C1 C 0.3202(3) 0.00771(19) 0.42806(9) 0.0217(5) Uani 1 1 d . . . C11 C 0.5808(3) 0.01313(19) 0.65079(9) 0.0230(5) Uani 1 1 d . . . C5 C 0.0016(3) 0.10223(19) 0.39856(10) 0.0258(5) Uani 1 1 d . . . H5 H -0.0881 0.1668 0.3997 0.031 Uiso 1 1 calc R . . C6 C 0.1867(3) 0.1029(2) 0.42816(9) 0.0236(5) Uani 1 1 d . . . H6 H 0.2256 0.1692 0.4492 0.028 Uiso 1 1 calc R . . C10 C 0.4419(3) 0.10400(19) 0.65156(10) 0.0232(5) Uani 1 1 d . . . H10 H 0.4716 0.1699 0.674 0.028 Uiso 1 1 calc R . . C3 C 0.0721(3) -0.08932(19) 0.36621(10) 0.0242(5) Uani 1 1 d . . . H4 H 0.0317 -0.1552 0.3451 0.029 Uiso 1 1 calc R . . C15 C 0.2994(4) 0.1087(2) 0.26227(12) 0.0415(6) Uani 1 1 d . . . H15A H 0.3223 0.1323 0.3022 0.062 Uiso 1 1 calc R . . H15B H 0.3775 0.0384 0.2546 0.062 Uiso 1 1 calc R . . H15C H 0.15 0.0951 0.256 0.062 Uiso 1 1 calc R . . C16 C 0.6441(3) 0.2327(2) 0.24331(11) 0.0316(5) Uani 1 1 d . . . H16A H 0.7125 0.2983 0.2251 0.047 Uiso 1 1 calc R . . H16B H 0.7244 0.1632 0.2352 0.047 Uiso 1 1 calc R . . H16C H 0.6373 0.2447 0.285 0.047 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 S 0.0291(3) 0.0313(3) 0.0209(3) -0.0023(2) -0.0005(2) -0.0028(2) O6 0.0249(7) 0.0283(9) 0.0255(8) -0.0017(7) -0.0025(7) -0.0009(7) O1 0.0255(9) 0.0322(10) 0.0341(10) -0.0054(8) -0.0067(8) -0.0035(8) O2 0.0218(7) 0.0304(9) 0.0262(8) -0.0033(7) -0.0014(7) 0.0010(7) O7 0.0299(8) 0.0294(9) 0.0371(10) -0.0056(7) -0.0085(8) 0.0052(8) O8 0.0258(8) 0.0331(10) 0.0342(9) -0.0011(8) -0.0068(7) 0.0028(8) O4 0.0248(8) 0.0345(10) 0.0336(9) 0.0003(8) -0.0066(7) 0.0027(7) O3 0.0302(8) 0.0285(9) 0.0445(10) -0.0098(7) -0.0128(8) 0.0067(8) O5 0.0262(8) 0.0278(9) 0.0304(9) -0.0043(8) -0.0052(7) -0.0047(7) C7 0.0223(10) 0.0248(12) 0.0199(11) -0.0028(9) 0.0065(9) -0.0086(10) C4 0.0172(10) 0.0288(12) 0.0214(11) 0.0047(10) 0.0030(8) -0.0027(9) C8 0.0236(10) 0.0258(12) 0.0194(10) 0.0010(9) 0.0059(9) -0.0054(10) O9 0.0341(8) 0.0379(10) 0.0356(9) 0.0010(7) -0.0013(7) 0.0095(8) C13 0.0287(11) 0.0216(11) 0.0238(11) 0.0004(9) 0.0053(9) -0.0048(10) C12 0.0240(10) 0.0242(12) 0.0284(12) 0.0065(10) 0.0064(9) 0.0024(9) C14 0.0226(10) 0.0265(12) 0.0178(11) 0.0017(10) 0.0059(9) -0.0081(10) C2 0.0206(10) 0.0234(11) 0.0226(11) -0.0013(9) 0.0031(9) -0.0008(9) C9 0.0206(10) 0.0225(11) 0.0222(11) 0.0019(9) 0.0044(9) 0.0004(9) C1 0.0218(10) 0.0242(12) 0.0192(11) 0.0021(9) 0.0030(8) -0.0049(9) C11 0.0193(10) 0.0293(12) 0.0204(11) 0.0065(9) 0.0016(9) -0.0030(9) C5 0.0239(11) 0.0232(12) 0.0303(12) 0.0040(10) 0.0052(9) 0.0047(10) C6 0.0277(11) 0.0219(11) 0.0212(11) -0.0006(9) 0.0061(9) -0.0044(9) C10 0.0246(11) 0.0229(12) 0.0220(11) -0.0009(9) -0.0004(9) -0.0015(9) C3 0.0244(11) 0.0225(11) 0.0257(12) -0.0014(9) 0.0016(9) -0.0024(9) C15 0.0412(13) 0.0371(14) 0.0463(15) 0.0050(12) 0.0031(12) -0.0115(12) C16 0.0260(11) 0.0344(13) 0.0342(13) -0.0062(11) 0.0015(10) -0.0006(10) #----------------------------------------------------------------------------# # MOLECULAR GEOMETRY # #----------------------------------------------------------------------------# _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 S O9 1.5246(17) . ? S C15 1.768(3) . ? S C16 1.780(2) . ? O6 C14 1.242(3) . ? O1 C7 1.315(3) . ? O1 H1 0.75(3) . ? O2 C7 1.248(3) . ? O7 C9 1.353(2) . ? O7 H8 0.99(3) . ? O8 C11 1.359(3) . ? O8 H9 0.781(17) . ? O4 C4 1.357(2) . ? O4 H3 0.86(3) . ? O3 C2 1.351(3) . ? O3 H2 0.98(3) . ? O5 C14 1.314(3) . ? O5 H7 0.86(3) . ? C7 C1 1.458(3) . ? C4 C3 1.375(3) . ? C4 C5 1.399(3) . ? C8 C13 1.402(3) . ? C8 C9 1.411(3) . ? C8 C14 1.456(3) . ? C13 C12 1.369(3) . ? C13 H12 0.95 . ? C12 C11 1.398(3) . ? C12 H11 0.95 . ? C2 C3 1.393(3) . ? C2 C1 1.400(3) . ? C9 C10 1.384(3) . ? C1 C6 1.405(3) . ? C11 C10 1.386(3) . ? C5 C6 1.370(3) . ? C5 H5 0.95 . ? C6 H6 0.95 . ? C10 H10 0.95 . ? C3 H4 0.95 . ? C15 H15A 0.98 . ? C15 H15B 0.98 . ? C15 H15C 0.98 . ? C16 H16A 0.98 . ? C16 H16B 0.98 . ? C16 H16C 0.98 . ? 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 O9 S C15 105.70(11) . . ? O9 S C16 104.79(10) . . ? C15 S C16 97.97(12) . . ? C7 O1 H1 111(2) . . ? C9 O7 H8 110.3(18) . . ? C11 O8 H9 109(2) . . ? C4 O4 H3 110(2) . . ? C2 O3 H2 108.9(19) . . ? C14 O5 H7 109.8(17) . . ? O2 C7 O1 122.14(19) . . ? O2 C7 C1 122.26(19) . . ? O1 C7 C1 115.6(2) . . ? O4 C4 C3 121.7(2) . . ? O4 C4 C5 117.8(2) . . ? C3 C4 C5 120.50(19) . . ? C13 C8 C9 117.99(19) . . ? C13 C8 C14 122.8(2) . . ? C9 C8 C14 119.2(2) . . ? C12 C13 C8 121.8(2) . . ? C12 C13 H12 119.1 . . ? C8 C13 H12 119.1 . . ? C13 C12 C11 119.2(2) . . ? C13 C12 H11 120.4 . . ? C11 C12 H11 120.4 . . ? O6 C14 O5 121.72(19) . . ? O6 C14 C8 122.1(2) . . ? O5 C14 C8 116.2(2) . . ? O3 C2 C3 117.06(19) . . ? O3 C2 C1 122.59(19) . . ? C3 C2 C1 120.3(2) . . ? O7 C9 C10 117.05(19) . . ? O7 C9 C8 122.37(18) . . ? C10 C9 C8 120.58(19) . . ? C2 C1 C6 118.31(19) . . ? C2 C1 C7 120.2(2) . . ? C6 C1 C7 121.48(19) . . ? O8 C11 C10 121.8(2) . . ? O8 C11 C12 117.43(19) . . ? C10 C11 C12 120.72(19) . . ? C6 C5 C4 119.5(2) . . ? C6 C5 H5 120.3 . . ? C4 C5 H5 120.3 . . ? C5 C6 C1 121.3(2) . . ? C5 C6 H6 119.3 . . ? C1 C6 H6 119.3 . . ? C9 C10 C11 119.7(2) . . ? C9 C10 H10 120.1 . . ? C11 C10 H10 120.1 . . ? C4 C3 C2 120.0(2) . . ? C4 C3 H4 120 . . ? C2 C3 H4 120 . . ? S C15 H15A 109.5 . . ? S C15 H15B 109.5 . . ? H15A C15 H15B 109.5 . . ? S C15 H15C 109.5 . . ? H15A C15 H15C 109.5 . . ? H15B C15 H15C 109.5 . . ? S C16 H16A 109.5 . . ? S C16 H16B 109.5 . . ? H16A C16 H16B 109.5 . . ? S C16 H16C 109.5 . . ? H16A C16 H16C 109.5 . . ? H16B C16 H16C 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 C9 C8 C13 C12 0.1(3) . . . . ? C14 C8 C13 C12 177.54(19) . . . . ? C8 C13 C12 C11 0.8(3) . . . . ? C13 C8 C14 O6 -174.7(2) . . . . ? C9 C8 C14 O6 2.8(3) . . . . ? C13 C8 C14 O5 5.1(3) . . . . ? C9 C8 C14 O5 -177.40(19) . . . . ? C13 C8 C9 O7 178.35(19) . . . . ? C14 C8 C9 O7 0.8(3) . . . . ? C13 C8 C9 C10 -1.2(3) . . . . ? C14 C8 C9 C10 -178.79(19) . . . . ? O3 C2 C1 C6 -179.76(18) . . . . ? C3 C2 C1 C6 0.6(3) . . . . ? O3 C2 C1 C7 -1.3(3) . . . . ? C3 C2 C1 C7 179.03(19) . . . . ? O2 C7 C1 C2 -3.4(3) . . . . ? O1 C7 C1 C2 177.63(19) . . . . ? O2 C7 C1 C6 174.99(19) . . . . ? O1 C7 C1 C6 -4.0(3) . . . . ? C13 C12 C11 O8 -179.83(19) . . . . ? C13 C12 C11 C10 -0.6(3) . . . . ? O4 C4 C5 C6 -178.36(19) . . . . ? C3 C4 C5 C6 1.8(3) . . . . ? C4 C5 C6 C1 -1.2(3) . . . . ? C2 C1 C6 C5 0.0(3) . . . . ? C7 C1 C6 C5 -178.4(2) . . . . ? O7 C9 C10 C11 -178.13(18) . . . . ? C8 C9 C10 C11 1.5(3) . . . . ? O8 C11 C10 C9 178.65(19) . . . . ? C12 C11 C10 C9 -0.5(3) . . . . ? O4 C4 C3 C2 178.93(19) . . . . ? C5 C4 C3 C2 -1.2(3) . . . . ? O3 C2 C3 C4 -179.64(19) . . . . ? C1 C2 C3 C4 0.0(3) . . . . ?