# Supplementary Material (ESI) for Chemical Communications # This journal is © The Royal Society of Chemistry 2003 data_global _journal_coden_Cambridge 182 _publ_contact_author_name 'Prof Jerome Lacour' _publ_contact_author_address ; Department of Organic Chemistry University of Geneva Quai Ernest Ansermet 30 Geneva 4 CH-1211 SWITZERLAND ; _publ_contact_author_email JEROME.LACOUR@CHIORG.UNIGE.CH _publ_requested_journal 'Chemical Communications' loop_ _publ_author_name _publ_author_address 'Celine Perollier' ; Departement de chimie organique Universite de Geneve CH - 1212 Geneve 4 Switzerland ; 'Samuel Constant' ; Departement de chimie organique Universite de Geneve CH - 1212 Geneve 4 Switzerland ; 'Jonathan J. Jodry' ; Departement de chimie organique Universite de Geneve CH - 1212 Geneve 4 Switzerland ; 'Gerald Bernardinelli' ; Laboratoire de Cristallographie Universite de Geneve 24, quai E. Ansermet CH - 1211 Geneve 4 Switzerland ; 'Jerome Lacour' ; Departement de chimie organique Universite de Geneve CH - 1212 Geneve 4 Switzerland ; _publ_section_title ; Mannose derived hexacoordinated phosphate - a generally efficient chiral anion for asymmetric applications ; data_PERO _database_code_CSD 210499 #----- Compound (+)-[Me2NH2][3](C3H6O)--------------------------------------- _audit_creation_date 2003-03-25 _audit_creation_method from_xtal_archive_file_using_CIFIO _audit_update_record 2003-03-25 _audit_conform_dict_name cif_core.dic _audit_conform_dict_version 2.0.1 #---------------------------------------------------------------------------- _chemical_name_systematic ; Dimethylammonium (\L)-Bis[3,4,5,6-tetrachlorobenzene-1,2-diolato] [D-6-Methoxy-2-phenyl-hexahydro-pyrano[3,2-d][1,3]dioxine-7,8- diolato]phosphate acetone solvate ; _chemical_formula_moiety '(C26 H16 O10 P Cl8) (C2 H8 N) (C3 H6 O)' _chemical_formula_sum 'C31 H30 N O11 P Cl8' _chemical_formula_weight 907.2 _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M 'C 2' loop_ _symmetry_equiv_pos_as_xyz +x,+y,+z -x,+y,-z 1/2+x,1/2+y,+z 1/2-x,1/2+y,-z _cell_length_a 18.5028(13) _cell_length_b 16.1920(8) _cell_length_c 14.6519(9) _cell_angle_alpha 90.00000 _cell_angle_beta 110.117(7) _cell_angle_gamma 90.00000 _cell_volume 4121.9(5) _cell_formula_units_Z 4 _exptl_crystal_density_diffrn 1.462 _exptl_crystal_density_meas not_measured _diffrn_radiation_type MoK\a _diffrn_radiation_wavelength .71073 _cell_measurement_reflns_used 8000 _cell_measurement_theta_min 2.55 _cell_measurement_theta_max 27.85 _cell_measurement_temperature 200 _exptl_absorpt_coefficient_mu .64 _exptl_crystal_description prism _exptl_crystal_size_max .23 _exptl_crystal_size_mid .19 _exptl_crystal_size_min .16 _exptl_crystal_colour colourless _diffrn_measurement_device_type 'Stoe Ipds' _diffrn_measurement_method \f _diffrn_detector_area_resol_mean 6 _exptl_absorpt_correction_type numerical _exptl_absorpt_process_details 'XRED; Stoe & Cie, 1999' _exptl_absorpt_correction_T_min .8679 _exptl_absorpt_correction_T_max .9235 _diffrn_reflns_number 31887 _reflns_number_total 9336 _reflns_number_gt 5943 _reflns_threshold_expression 'refl observed if Fo > 4.0 \s(Fo)' _diffrn_reflns_theta_max 28.14 _diffrn_reflns_av_R_equivalents .046 _diffrn_reflns_limit_h_min -24 _diffrn_reflns_limit_h_max 24 _diffrn_reflns_limit_k_min -21 _diffrn_reflns_limit_k_max 21 _diffrn_reflns_limit_l_min -19 _diffrn_reflns_limit_l_max 19 _diffrn_standards_decay_% 0 _refine_ls_structure_factor_coef F _refine_ls_R_factor_gt .036 _refine_ls_wR_factor_ref .036 _refine_ls_goodness_of_fit_ref 1.80(3) _refine_ls_number_reflns 5943 _refine_ls_number_parameters 511 _refine_ls_weighting_scheme calc _refine_ls_weighting_details \w=1/[\s^2^(Fo)+0.0002(Fo^2^)] _refine_ls_hydrogen_treatment noref _refine_ls_shift/su_max .173 _refine_diff_density_max .555 _refine_diff_density_min -.339 _refine_ls_extinction_method none _refine_ls_abs_structure_details Flack_xabs_refined _refine_ls_abs_structure_Flack .01(7) _refine_special_details ; - The dimethylamonium "a" is located on a C2 axis with the N atom in spécial position 2b and a global multiplicity of 0.5 - The dimethylamonium "b" is disordered and located on a C2 axis with the N atom in spécial position 2a and a global multiplicity of 0.5 - The acetone "c" is located in general position with all atomic population parameters of 0.5 - The acetone "d" is disordered and located around a C2 axis with a global multiplicity of 0.5 ; _computing_data_collection 'EXPOSE (Stoe & Cie, 1999)' _computing_cell_refinement 'CELL (Stoe & Cie, 1999)' _computing_data_reduction 'XRED (Stoe & Cie, 1999)' _computing_structure_solution SIR97 _computing_structure_refinement xtal_CRYLSQ _computing_molecular_graphics xtal_gx3 _computing_publication_material xtal_CIFIO loop_ _atom_type_symbol _atom_type_scat_source _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag C Int._Tables_Vol_IV_Tables_2.2B_and_2.3.1 .002 .002 H Int._Tables_Vol_IV_Tables_2.2B_and_2.3.1 0 0 N Int._Tables_Vol_IV_Tables_2.2B_and_2.3.1 .004 .003 O Int._Tables_Vol_IV_Tables_2.2B_and_2.3.1 .008 .006 P Int._Tables_Vol_IV_Tables_2.2B_and_2.3.1 .09 .095 Cl Int._Tables_Vol_IV_Tables_2.2B_and_2.3.1 .132 .159 loop_ _atom_site_label _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_occupancy _atom_site_adp_type P1 .50626(8) .16351(11) .24949(12) .0314(7) 1.00000 Uani O1 .47656(19) .0645(3) .2654(3) .0339(19) 1.00000 Uani O2 .5430(3) .1270(3) .1628(4) .039(3) 1.00000 Uani O3 .59141(19) .1372(3) .3432(3) .0353(19) 1.00000 Uani O4 .5457(2) .2592(3) .2384(3) .036(2) 1.00000 Uani O5 .47028(19) .1996(3) .3328(3) .0320(19) 1.00000 Uani O6 .4260(2) .1881(3) .1591(3) .036(2) 1.00000 Uani O7 .2622(2) .1312(3) .1053(4) .038(2) 1.00000 Uani O8 .1613(2) .1024(3) .1628(4) .049(3) 1.00000 Uani O9 .3113(3) .2117(3) .3528(4) .038(2) 1.00000 Uani O10 .3249(3) .3507(3) .3191(4) .050(3) 1.00000 Uani Cl1 .45816(11) -.11808(12) .30355(15) .0602(10) 1.00000 Uani Cl2 .53542(12) -.23195(13) .18711(17) .0755(12) 1.00000 Uani Cl3 .61845(12) -.15180(16) .05587(17) .0784(13) 1.00000 Uani Cl4 .62165(10) .04354(15) .03779(15) .0663(11) 1.00000 Uani Cl5 .75084(8) .10035(12) .48417(13) .0490(8) 1.00000 Uani Cl6 .85888(9) .25808(15) .51995(18) .0775(12) 1.00000 Uani Cl7 .79695(10) .41836(14) .3999(2) .0873(13) 1.00000 Uani Cl8 .62963(9) .42259(12) .24494(15) .0577(9) 1.00000 Uani C1 .5072(3) .0085(4) .2216(5) .036(3) 1.00000 Uani C2 .5040(4) -.0765(5) .2300(5) .045(4) 1.00000 Uani C3 .5393(4) -.1266(5) .1779(6) .052(4) 1.00000 Uani C4 .5762(4) -.0906(5) .1203(6) .053(4) 1.00000 Uani C5 .5790(3) -.0044(6) .1114(5) .048(4) 1.00000 Uani C6 .5449(3) .0436(5) .1624(5) .042(4) 1.00000 Uani C7 .6443(3) .1971(4) .3609(5) .031(3) 1.00000 Uani C8 .7182(3) .1922(4) .4252(5) .039(3) 1.00000 Uani C9 .7661(3) .2617(5) .4376(5) .048(4) 1.00000 Uani C10 .7384(4) .3328(4) .3832(6) .050(4) 1.00000 Uani C11 .6639(4) .3363(4) .3153(5) .043(4) 1.00000 Uani C12 .6178(3) .2677(4) .3038(5) .035(3) 1.00000 Uani C13 .4111(3) .2593(4) .2897(5) .033(3) 1.00000 Uani C14 .3677(3) .2226(4) .1907(5) .033(3) 1.00000 Uani C15 .3109(3) .1579(4) .1996(5) .036(3) 1.00000 Uani C16 .2097(3) .0694(4) .1161(5) .041(3) 1.00000 Uani C17 .2042(4) .1272(4) .2604(6) .044(4) 1.00000 Uani C18 .2625(3) .1920(4) .2548(5) .036(3) 1.00000 Uani C19 .3636(3) .2755(4) .3549(5) .036(3) 1.00000 Uani C20 .2796(5) .3805(5) .3733(7) .070(5) 1.00000 Uani C21 .1622(4) .0410(4) .0144(6) .049(4) 1.00000 Uani C22 .1940(4) -.0154(4) -.0308(6) .053(4) 1.00000 Uani C23 .1518(5) -.0408(5) -.1256(7) .071(5) 1.00000 Uani C24 .0779(5) -.0122(6) -.1705(7) .074(5) 1.00000 Uani C25 .0471(4) .0431(6) -.1246(7) .078(5) 1.00000 Uani C26 .0894(4) .0716(5) -.0332(7) .064(5) 1.00000 Uani N1a .50000 .1006(4) .50000 .031(4) 1.00000 Uani C1a .4300(4) .0497(4) .4729(5) .043(4) 1.00000 Uani N1b .50000 .2635(6) .00000 .099(9) 1.00000 Uani C1b .4220(8) .2766(10) -.0283(14) .075(11) .50000 Uani C2b .5405(9) .3427(11) -.0140(15) .094(13) .50000 Uani C1c .2404(14) .2289(11) -.1522(17) .087(13) .50000 Uani C2c .1988(19) .1694(14) -.222(3) .129(19) .50000 Uani C3c .1998(9) .2599(11) -.0988(11) .065(9) .50000 Uani O1c .3151(11) .2427(10) -.1286(19) .155(15) .50000 Uani C1d .5096(19) .4622(13) .483(3) .14(3) .50000 Uani C2d .542(2) .525(2) .439(3) .15(3) .50000 Uani C3d .471(5) .485(3) .548(6) .23(4) .50000 Uiso O1d .5124(16) .3938(14) .462(2) .18(3) .50000 Uani H13 .42984 .31649 .28323 .05000 1.00000 Uiso H14 .33704 .26548 .14409 .05000 1.00000 Uiso H15 .34080 .11249 .23549 .05000 1.00000 Uiso H16 .23820 .02508 .15598 .05000 1.00000 Uiso H171 .16969 .15321 .29127 .05000 1.00000 Uiso H172 .23112 .08171 .29848 .05000 1.00000 Uiso H18 .23520 .24278 .22120 .05000 1.00000 Uiso H19 .39615 .28021 .42310 .05000 1.00000 Uiso H201 .24073 .34014 .37074 .05000 1.00000 Uiso H202 .31316 .39005 .44106 .05000 1.00000 Uiso H203 .25323 .43425 .34928 .05000 1.00000 Uiso H22 .24522 -.03587 .00226 .05000 1.00000 Uiso H23 .17399 -.07743 -.15984 .05000 1.00000 Uiso H24 .04761 -.02854 -.23625 .05000 1.00000 Uiso H25 -.00466 .06445 -.15670 .05000 1.00000 Uiso H26 .06710 .11467 -.00244 .05000 1.00000 Uiso H01a .50213 .13761 .55544 .05000 1.00000 Uiso H11a .42654 .01723 .41565 .05000 1.00000 Uiso H12a .43224 .01514 .52731 .05000 1.00000 Uiso H13a .38451 .08722 .45764 .05000 1.00000 Uiso H01b .51975 .24940 .06819 .05000 .50000 Uiso H02b .51027 .22084 -.03887 .05000 .50000 Uiso H11b .41270 .33367 -.00698 .05000 .50000 Uiso H12b .39947 .27437 -.09903 .05000 .50000 Uiso H13b .39924 .23660 .00186 .05000 .50000 Uiso H21b .51370 .36618 -.08000 .05000 .50000 Uiso H22b .53861 .38587 .03384 .05000 .50000 Uiso H23b .59370 .33225 -.00674 .05000 .50000 Uiso H21c .22625 .15829 -.26540 .05000 .50000 Uiso H22c .19224 .12124 -.18862 .05000 .50000 Uiso H23c .14764 .19351 -.25955 .05000 .50000 Uiso H31c .22061 .23880 -.03370 .05000 .50000 Uiso H32c .20347 .32026 -.09714 .05000 .50000 Uiso H33c .14632 .24432 -.12836 .05000 .50000 Uiso H21d .59691 .53480 .47778 .05000 .50000 Uiso H22d .53826 .50896 .37329 .05000 .50000 Uiso H23d .51422 .57825 .43484 .05000 .50000 Uiso H31d .44009 .53343 .52539 .05000 .50000 Uiso H32d .44396 .43952 .56080 .05000 .50000 Uiso H33d .51356 .50133 .61266 .05000 .50000 Uiso loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_12 _atom_site_aniso_U_13 _atom_site_aniso_U_23 P1 .0315(7) .0342(8) .0275(9) -.0082(6) .0088(6) -.0003(7) O1 .0340(18) .032(3) .037(3) -.0072(15) .0138(18) -.0042(17) O2 .038(3) .042(3) .038(3) -.0046(17) .0150(19) -.0027(19) O3 .0336(18) .036(3) .033(3) -.0084(16) .0080(17) .0016(17) O4 .0328(18) .039(3) .033(3) -.0098(16) .0074(17) .0063(19) O5 .0342(18) .033(2) .026(3) -.0039(15) .0067(17) -.0003(16) O6 .0346(19) .042(3) .029(3) -.0070(16) .0092(17) -.0018(17) O7 .0310(18) .040(3) .038(3) -.0069(16) .0065(18) -.0051(18) O8 .0274(18) .056(3) .056(4) -.0100(18) .007(2) -.010(3) O9 .045(3) .034(3) .036(3) -.0062(17) .0141(19) -.0029(18) O10 .061(3) .033(3) .057(4) .006(2) .024(3) -.002(3) Cl1 .0782(12) .0361(9) .0743(15) -.0113(8) .0364(10) -.0057(9) Cl2 .0931(14) .0449(10) .0831(17) .0157(10) .0234(12) -.0113(10) Cl3 .0786(12) .0892(14) .0692(16) .0312(11) .0276(11) -.0194(12) Cl4 .0594(10) .0964(14) .0537(14) .0047(10) .0330(10) -.0065(10) Cl5 .0376(7) .0497(9) .0544(12) .0101(7) .0090(7) .0045(8) Cl6 .0301(7) .0773(13) .1027(17) -.0070(8) -.0057(8) -.0095(12) Cl7 .0490(10) .0550(11) .139(3) -.0292(9) .0078(11) -.0027(12) Cl8 .0524(9) .0394(9) .0782(14) -.0122(7) .0183(9) .0116(9) C1 .032(3) .037(4) .036(4) -.003(3) .007(3) -.005(3) C2 .042(3) .043(4) .047(5) -.002(3) .010(3) -.010(4) C3 .050(4) .047(4) .049(5) .008(3) .004(4) -.016(4) C4 .048(4) .069(5) .041(5) .012(4) .013(4) -.013(4) C5 .035(3) .061(5) .047(5) .008(4) .011(3) -.010(4) C6 .034(3) .055(4) .031(5) -.003(3) .004(3) -.008(3) C7 .031(3) .033(3) .032(4) -.005(3) .013(3) -.005(3) C8 .031(3) .045(4) .043(5) .000(3) .015(3) -.003(3) C9 .028(3) .053(4) .057(5) -.000(3) .006(3) -.009(4) C10 .037(3) .041(4) .068(6) -.014(3) .014(4) -.009(4) C11 .037(3) .038(4) .054(5) -.008(3) .015(3) -.006(3) C12 .031(3) .037(4) .040(4) -.006(3) .015(3) -.002(3) C13 .038(3) .025(3) .033(4) -.005(3) .007(3) .004(3) C14 .032(3) .031(3) .033(4) -.002(3) .006(3) -.003(3) C15 .033(3) .034(3) .035(4) -.006(3) .004(3) .004(3) C16 .035(3) .035(4) .051(5) -.005(3) .013(3) -.006(3) C17 .044(4) .040(4) .052(5) -.005(3) .019(4) -.004(3) C18 .025(3) .034(3) .044(5) -.002(3) .006(3) -.002(3) C19 .044(3) .031(3) .030(4) -.003(3) .009(3) -.002(3) C20 .083(5) .053(5) .084(7) .013(4) .042(5) -.004(4) C21 .036(3) .047(4) .059(5) -.015(3) .012(3) -.011(4) C22 .044(4) .047(5) .066(6) -.010(3) .017(4) -.016(4) C23 .074(5) .063(5) .076(7) -.022(4) .024(5) -.034(5) C24 .075(5) .070(6) .063(6) -.023(5) .002(5) -.027(5) C25 .049(4) .078(6) .081(8) -.006(4) -.011(4) -.009(5) C26 .041(4) .060(5) .075(7) -.004(3) -.001(4) -.016(4) N1a .035(4) .032(4) .025(5) .00000 .010(3) .00000 C1a .038(3) .054(4) .042(5) -.007(3) .018(3) -.008(4) N1b .214(16) .055(6) .014(7) .00000 .021(7) .00000 C1b .073(11) .095(13) .061(13) -.013(10) .029(10) .018(11) C2b .089(12) .098(14) .073(16) -.024(12) .002(10) -.016(12) C1c .156(19) .046(10) .104(16) -.003(11) .102(16) .022(10) C2c .23(3) .086(15) .13(3) -.009(17) .15(3) .039(16) C3c .078(9) .084(11) .031(10) .029(9) .017(8) .019(8) O1c .150(14) .093(11) .29(3) -.001(10) .157(17) .025(13) C1d .04(2) .126(19) .19(5) -.03(2) -.017(18) .09(4) C2d .12(2) .18(4) .14(3) -.07(3) .044(18) -.07(3) O1d .12(2) .145(16) .19(4) -.042(16) -.044(19) .045(17) loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_site_symmetry_1 _geom_bond_site_symmetry_2 _geom_bond_distance P1 O1 . . 1.736(5) P1 O2 . . 1.737(6) P1 O3 . . 1.749(4) P1 O4 . . 1.744(5) P1 O5 . . 1.683(5) P1 O6 . . 1.663(4) O1 C1 . . 1.344(8) O2 C6 . . 1.350(8) O3 C7 . . 1.338(7) O4 C12 . . 1.355(6) O5 C13 . . 1.435(6) O6 C14 . . 1.427(8) O7 C15 . . 1.432(7) O7 C16 . . 1.440(8) O8 C16 . . 1.407(9) O8 C17 . . 1.433(8) O9 C18 . . 1.445(7) O9 C19 . . 1.409(7) O10 C19 . . 1.418(7) O10 C20 . . 1.424(12) Cl1 C2 . . 1.722(8) Cl2 C3 . . 1.715(8) Cl3 C4 . . 1.729(9) Cl4 C5 . . 1.725(8) Cl5 C8 . . 1.722(7) Cl6 C9 . . 1.726(6) Cl7 C10 . . 1.724(7) Cl8 C11 . . 1.723(7) C1 C2 . . 1.385(10) C1 C6 . . 1.406(10) C2 C3 . . 1.417(11) C3 C4 . . 1.384(12) C4 C5 . . 1.405(12) C5 C6 . . 1.373(11) C7 C8 . . 1.371(7) C7 C12 . . 1.401(8) C8 C9 . . 1.405(9) C9 C10 . . 1.393(10) C10 C11 . . 1.397(8) C11 C12 . . 1.375(9) C13 C14 . . 1.516(8) C13 C19 . . 1.526(10) C14 C15 . . 1.522(8) C15 C18 . . 1.502(10) C16 C21 . . 1.518(9) C17 C18 . . 1.528(9) C21 C22 . . 1.374(11) C21 C26 . . 1.379(9) C22 C23 . . 1.400(11) C23 C24 . . 1.379(11) C24 C25 . . 1.358(14) C25 C26 . . 1.378(12) N1a C1a . . 1.469(7) N1a C1a . 2_656 1.469(7) N1b C1b . . 1.375(14) N1b C2b . . 1.53(2) N1b C1b . 2_655 1.375(14) N1b C2b . 2_655 1.53(2) C1c C2c . . 1.43(4) C1c C3c . . 1.35(4) C1c O1c . . 1.32(4) C1d C2d . . 1.44(5) C1d C3d . . 1.42(10) C1d O1d . . 1.16(4) loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_2 _geom_angle_site_symmetry_3 _geom_angle O1 P1 O2 . . . 90.3(3) O1 P1 O3 . . . 84.90(18) O1 P1 O4 . . . 174.12(18) O1 P1 O5 . . . 90.0(3) O1 P1 O6 . . . 95.22(18) O2 P1 O3 . . . 91.0(2) O2 P1 O4 . . . 87.3(3) O2 P1 O5 . . . 179.5(3) O2 P1 O6 . . . 88.1(3) O3 P1 O4 . . . 89.77(18) O3 P1 O5 . . . 89.4(2) O3 P1 O6 . . . 179.0(3) O4 P1 O5 . . . 92.4(3) O4 P1 O6 . . . 90.07(19) O5 P1 O6 . . . 91.5(2) P1 O1 C1 . . . 110.7(4) P1 O2 C6 . . . 111.2(5) P1 O3 C7 . . . 112.1(4) P1 O4 C12 . . . 111.5(4) P1 O5 C13 . . . 110.3(4) P1 O6 C14 . . . 113.8(4) C15 O7 C16 . . . 109.1(5) C16 O8 C17 . . . 111.4(5) C18 O9 C19 . . . 111.9(5) C19 O10 C20 . . . 113.9(6) O1 C1 C2 . . . 126.2(7) O1 C1 C6 . . . 113.7(6) C2 C1 C6 . . . 120.1(7) Cl1 C2 C1 . . . 119.3(6) Cl1 C2 C3 . . . 122.0(6) C1 C2 C3 . . . 118.6(7) Cl2 C3 C2 . . . 119.2(7) Cl2 C3 C4 . . . 120.6(7) C2 C3 C4 . . . 120.2(7) Cl3 C4 C3 . . . 120.2(6) Cl3 C4 C5 . . . 118.8(7) C3 C4 C5 . . . 121.0(8) Cl4 C5 C4 . . . 122.9(6) Cl4 C5 C6 . . . 118.7(7) C4 C5 C6 . . . 118.4(7) O2 C6 C1 . . . 112.5(6) O2 C6 C5 . . . 125.9(7) C1 C6 C5 . . . 121.6(7) O3 C7 C8 . . . 125.6(5) O3 C7 C12 . . . 113.1(4) C8 C7 C12 . . . 121.3(6) Cl5 C8 C7 . . . 119.3(5) Cl5 C8 C9 . . . 122.1(4) C7 C8 C9 . . . 118.6(6) Cl6 C9 C8 . . . 119.6(5) Cl6 C9 C10 . . . 120.7(5) C8 C9 C10 . . . 119.7(5) Cl7 C10 C9 . . . 119.5(5) Cl7 C10 C11 . . . 119.1(5) C9 C10 C11 . . . 121.3(6) Cl8 C11 C10 . . . 121.9(5) Cl8 C11 C12 . . . 119.8(4) C10 C11 C12 . . . 118.2(6) O4 C12 C7 . . . 113.4(5) O4 C12 C11 . . . 125.9(5) C7 C12 C11 . . . 120.7(5) O5 C13 C14 . . . 103.3(5) O5 C13 C19 . . . 110.9(5) C14 C13 C19 . . . 115.9(5) O6 C14 C13 . . . 104.6(4) O6 C14 C15 . . . 112.3(5) C13 C14 C15 . . . 110.0(6) O7 C15 C14 . . . 110.4(5) O7 C15 C18 . . . 109.7(4) C14 C15 C18 . . . 110.5(5) O7 C16 O8 . . . 110.9(5) O7 C16 C21 . . . 106.7(6) O8 C16 C21 . . . 110.0(5) O8 C17 C18 . . . 107.3(6) O9 C18 C15 . . . 109.4(4) O9 C18 C17 . . . 108.0(6) C15 C18 C17 . . . 109.8(5) O9 C19 O10 . . . 111.4(5) O9 C19 C13 . . . 113.6(5) O10 C19 C13 . . . 104.0(5) C16 C21 C22 . . . 118.4(5) C16 C21 C26 . . . 121.5(7) C22 C21 C26 . . . 120.1(7) C21 C22 C23 . . . 119.2(6) C22 C23 C24 . . . 119.9(9) C23 C24 C25 . . . 120.1(8) C24 C25 C26 . . . 120.5(7) C21 C26 C25 . . . 120.1(8) C1b N1b C2b . . . 109.9(11) C1b N1b C2b 2_655 . 2_655 109.9(11) C2c C1c C3c . . . 113(3) C2c C1c O1c . . . 124(3) C3c C1c O1c . . . 121.6(19) C2d C1d C3d . . . 120(3) C2d C1d O1d . . . 120(4) C3d C1d O1d . . . 120(4) 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_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion O2 P1 O1 C1 . . . . 11.6(4) O3 P1 O1 C1 . . . . -79.4(4) O4 P1 O1 C1 . . . . -54(3) O5 P1 O1 C1 . . . . -168.8(3) O6 P1 O1 C1 . . . . 99.7(4) O1 P1 O2 C6 . . . . -11.4(4) O3 P1 O2 C6 . . . . 73.5(4) O4 P1 O2 C6 . . . . 163.3(4) O5 P1 O2 C6 . . . . -142(22) O6 P1 O2 C6 . . . . -106.6(4) O1 P1 O3 C7 . . . . 176.4(5) O2 P1 O3 C7 . . . . 86.2(5) O4 P1 O3 C7 . . . . -1.1(5) O5 P1 O3 C7 . . . . -93.5(5) O6 P1 O3 C7 . . . . 79(13) O1 P1 O4 C12 . . . . -26(3) O2 P1 O4 C12 . . . . -91.9(5) O3 P1 O4 C12 . . . . -.9(5) O5 P1 O4 C12 . . . . 88.5(5) O6 P1 O4 C12 . . . . -180.0(5) O1 P1 O5 C13 . . . . -118.8(4) O2 P1 O5 C13 . . . . 12(22) O3 P1 O5 C13 . . . . 156.3(4) O4 P1 O5 C13 . . . . 66.5(4) O6 P1 O5 C13 . . . . -23.6(4) O1 P1 O6 C14 . . . . 88.2(4) O2 P1 O6 C14 . . . . 178.3(4) O3 P1 O6 C14 . . . . -175(13) O4 P1 O6 C14 . . . . -94.3(4) O5 P1 O6 C14 . . . . -1.9(4) P1 O1 C1 C2 . . . . 171.1(5) P1 O1 C1 C6 . . . . -9.2(5) P1 O2 C6 C1 . . . . 8.4(5) P1 O2 C6 C5 . . . . -171.6(5) P1 O3 C7 C8 . . . . -175.2(6) P1 O3 C7 C12 . . . . 2.8(7) P1 O4 C12 C7 . . . . 2.7(7) P1 O4 C12 C11 . . . . -178.5(6) P1 O5 C13 C14 . . . . 40.1(5) P1 O5 C13 C19 . . . . 164.9(4) P1 O6 C14 C13 . . . . 24.7(5) P1 O6 C14 C15 . . . . -94.6(5) C16 O7 C15 C14 . . . . 179.4(5) C16 O7 C15 C18 . . . . -58.7(6) C15 O7 C16 O8 . . . . 62.6(6) C15 O7 C16 C21 . . . . -177.6(5) C17 O8 C16 O7 . . . . -64.3(6) C17 O8 C16 C21 . . . . 178.0(5) C16 O8 C17 C18 . . . . 59.3(6) C19 O9 C18 C15 . . . . 64.6(6) C19 O9 C18 C17 . . . . -175.9(5) C18 O9 C19 O10 . . . . 64.1(7) C18 O9 C19 C13 . . . . -52.9(6) C20 O10 C19 O9 . . . . 60.5(7) C20 O10 C19 C13 . . . . -176.8(5) O1 C1 C2 Cl1 . . . . -.8(7) O1 C1 C2 C3 . . . . 179.7(5) C6 C1 C2 Cl1 . . . . 179.5(4) C6 C1 C2 C3 . . . . -.1(8) O1 C1 C6 O2 . . . . .5(6) O1 C1 C6 C5 . . . . -179.4(5) C2 C1 C6 O2 . . . . -179.7(5) C2 C1 C6 C5 . . . . .3(8) Cl1 C2 C3 Cl2 . . . . .8(7) Cl1 C2 C3 C4 . . . . -179.3(5) C1 C2 C3 Cl2 . . . . -179.7(4) C1 C2 C3 C4 . . . . .2(9) Cl2 C3 C4 Cl3 . . . . .5(8) Cl2 C3 C4 C5 . . . . 179.3(5) C2 C3 C4 Cl3 . . . . -179.4(5) C2 C3 C4 C5 . . . . -.6(9) Cl3 C4 C5 Cl4 . . . . .8(7) Cl3 C4 C5 C6 . . . . 179.6(4) C3 C4 C5 Cl4 . . . . -178.0(5) C3 C4 C5 C6 . . . . .9(8) Cl4 C5 C6 O2 . . . . -1.8(7) Cl4 C5 C6 C1 . . . . 178.2(4) C4 C5 C6 O2 . . . . 179.3(5) C4 C5 C6 C1 . . . . -.7(8) O3 C7 C8 Cl5 . . . . 4.7(10) O3 C7 C8 C9 . . . . -178.1(7) C12 C7 C8 Cl5 . . . . -173.3(6) C12 C7 C8 C9 . . . . 3.9(11) O3 C7 C12 O4 . . . . -3.6(9) O3 C7 C12 C11 . . . . 177.5(7) C8 C7 C12 O4 . . . . 174.6(7) C8 C7 C12 C11 . . . . -4.3(11) Cl5 C8 C9 Cl6 . . . . -4.2(10) Cl5 C8 C9 C10 . . . . 175.7(7) C7 C8 C9 Cl6 . . . . 178.6(6) C7 C8 C9 C10 . . . . -1.4(11) Cl6 C9 C10 Cl7 . . . . -1.0(10) Cl6 C9 C10 C11 . . . . 179.2(7) C8 C9 C10 Cl7 . . . . 179.1(6) C8 C9 C10 C11 . . . . -.7(12) Cl7 C10 C11 Cl8 . . . . 2.1(10) Cl7 C10 C11 C12 . . . . -179.4(6) C9 C10 C11 Cl8 . . . . -178.0(7) C9 C10 C11 C12 . . . . .5(12) Cl8 C11 C12 O4 . . . . 1.8(11) Cl8 C11 C12 C7 . . . . -179.5(6) C10 C11 C12 O4 . . . . -176.7(7) C10 C11 C12 C7 . . . . 2.0(11) O5 C13 C14 O6 . . . . -39.4(6) O5 C13 C14 C15 . . . . 81.5(6) C19 C13 C14 O6 . . . . -160.9(5) C19 C13 C14 C15 . . . . -40.0(6) O5 C13 C19 O9 . . . . -75.7(5) O5 C13 C19 O10 . . . . 163.1(4) C14 C13 C19 O9 . . . . 41.7(7) C14 C13 C19 O10 . . . . -79.6(6) O6 C14 C15 O7 . . . . -71.9(6) O6 C14 C15 C18 . . . . 166.6(5) C13 C14 C15 O7 . . . . 172.0(5) C13 C14 C15 C18 . . . . 50.5(6) O7 C15 C18 O9 . . . . 174.7(5) O7 C15 C18 C17 . . . . 56.3(6) C14 C15 C18 O9 . . . . -63.3(6) C14 C15 C18 C17 . . . . 178.3(5) O7 C16 C21 C22 . . . . 80.1(8) O7 C16 C21 C26 . . . . -98.7(8) O8 C16 C21 C22 . . . . -159.5(7) O8 C16 C21 C26 . . . . 21.6(9) O8 C17 C18 O9 . . . . -174.4(5) O8 C17 C18 C15 . . . . -55.2(6) C16 C21 C22 C23 . . . . -178.4(7) C26 C21 C22 C23 . . . . .4(12) C16 C21 C26 C25 . . . . -178.6(8) C22 C21 C26 C25 . . . . 2.6(12) C21 C22 C23 C24 . . . . -3.1(13) C22 C23 C24 C25 . . . . 2.7(14) C23 C24 C25 C26 . . . . .3(15) C24 C25 C26 C21 . . . . -3.0(14)