# Supplementary Material (ESI) for New Journal of Chemistry # This journal is © The Royal Society of Chemistry and # The Centre National de la Recherche Scientifique, 2002 data_global _journal_coden_Cambridge 440 loop_ _publ_author_name 'Aleksandra Skowronska' 'Ewa Krawczyk' 'Krzysztof Owsianik' 'Michal Wieczorek' _publ_contact_author_name 'Prof Aleksandra Skowronska' _publ_contact_author_address ; Centre of Molecular and Macrom Polish Academy of Sciences Sienkiewicza 112 Lodz 90-363 POLAND ; _publ_contact_author_email 'ASKOW@BILBO.CBMM.LODZ.PL' _publ_requested_journal 'New Journal of Chemistry' _publ_section_title ; An Expedient, Stereoselective Synthesis of Highly Functionalized Cyclic Compounds ; data_Compound9d _database_code_CSD 195722 _audit_creation_method SHELXL _chemical_name_systematic ; ? ; _chemical_name_common ; Ethyl 1-[(diethoxyphosphoryl)sulfanyl]-5- phenyl-2-oxocyclohexanecarboxylate ; _chemical_formula_moiety 'C19 H27 O6 P S' _chemical_formula_structural ? _chemical_formula_analytical ? _chemical_formula_sum 'C19 H27 O6 P S' _chemical_formula_weight 414.44 _chemical_melting_point ? _chemical_compound_source ? loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source 'C' 'C' 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 'H' 'H' 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 'O' 'O' 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 'P' 'P' 0.2955 0.4335 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 'S' 'S' 0.3331 0.5567 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M 'C 2/c' _symmetry_space_group_name_Hall '-C 2yc' 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 17.797(12) _cell_length_b 10.521(4) _cell_length_c 23.330(12) _cell_angle_alpha 90.00 _cell_angle_beta 106.53(5) _cell_angle_gamma 90.00 _cell_volume 4188.0(38) _cell_formula_units_Z 8 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used 25 _cell_measurement_theta_min 21.86 _cell_measurement_theta_max 27.67 _exptl_crystal_description 'monoclinic prism' _exptl_crystal_colour 'colourless' _exptl_crystal_size_max 0.88 _exptl_crystal_size_mid 0.40 _exptl_crystal_size_min 0.20 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.315 _exptl_crystal_density_method ? _exptl_crystal_F_000 1760 _exptl_absorpt_coefficient_mu 2.369 _exptl_absorpt_correction_type 'empirical' _exptl_absorpt_process_details ; (\y scans; North, Phillips, Mathews, 1968; Frenz, 1986) ; _exptl_absorpt_correction_T_min 0.8439 _exptl_absorpt_correction_T_max 0.9994 _exptl_special_details ; ? ; _diffrn_ambient_temperature 293(2) _diffrn_radiation_wavelength 1.54178 _diffrn_radiation_type CuK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device 'Enraf-Nonius CAD-4' _diffrn_measurement_method '\w/2\q scans' _diffrn_standards_number 3 _diffrn_standards_interval_count ? _diffrn_standards_interval_time 60 _diffrn_standards_decay_% 3.5 _diffrn_reflns_number 8572 _diffrn_reflns_av_R_equivalents 0.0731 _diffrn_reflns_av_sigmaI/netI 0.0579 _diffrn_reflns_limit_h_min -22 _diffrn_reflns_limit_h_max 22 _diffrn_reflns_limit_k_min -13 _diffrn_reflns_limit_k_max 12 _diffrn_reflns_limit_l_min -12 _diffrn_reflns_limit_l_max 29 _diffrn_reflns_theta_min 3.95 _diffrn_reflns_theta_max 75.60 _reflns_number_total 4315 _reflns_number_gt 3553 _reflns_threshold_expression >2sigma(I) #+------------------------------------------------------------ _computing_data_collection ; Enraf--Nonius CAD-4 (Schagen, Straver, van Meurs & Williams, 1989) ; _computing_cell_refinement ; Enraf--Nonius CAD-4 (Schagen, Straver, van Meurs & Williams, 1989) ; _computing_data_reduction ; Enraf--Nonius SDP (Frenz, 1986; North, Phillips & Mathews, 1968) ; _computing_structure_solution ; SHELXS-86 (Sheldrick, 1990) ; _computing_structure_refinement ; SHELXL-93 (Sheldrick, 1993) ; _computing_molecular_graphics ; SHELXTL-Plus - XP (Sheldrick, 1991) ; _computing_publication_material ; CSU (Vickovic, 1988) ; #+------------------------------------------------------------ _refine_special_details ; Refinement on F^2^ for ALL reflections except for 206 with very negative F^2^ or flagged by the user for potential systematic errors. Weighted R-factors wR and all goodnesses 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 observed criterion of F^2^ > 2sigma(F^2^) is used only for calculating _R_factor_obs 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. Hydrogen atoms were placed geometrically at idealised positions, and set as riding with fixed thermal parameters equal to 1.33 times of the equivalent isotropic thermal parameter of the parent-atom. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme 'calc' _refine_ls_weighting_details 'w=1/[\s^2^(Fo^2^)+(0.0647P)^2^+2.7789P] 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 SHELXL _refine_ls_extinction_coef 0.00099(9) _refine_ls_extinction_expression 'Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^' _refine_ls_number_reflns 4109 _refine_ls_number_parameters 248 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0618 _refine_ls_R_factor_gt 0.0484 _refine_ls_wR_factor_all 0.1710 _refine_ls_wR_factor_ref 0.1358 _refine_ls_goodness_of_fit_all 1.093 _refine_ls_goodness_of_fit_ref 1.099 _refine_ls_restrained_S_all 1.250 _refine_ls_restrained_S_obs 1.099 _refine_ls_shift/su_max -0.001 _refine_ls_shift/esd_mean 0.000 _refine_diff_density_max 0.249 _refine_diff_density_min -0.327 _refine_diff_density_rms 0.057 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_thermal_displace_type _atom_site_occupancy _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_group P1 P 0.32727(3) 0.61344(5) 0.25238(2) 0.0492(2) Uani 1 d . . S1 S 0.43942(3) 0.63614(5) 0.31098(2) 0.0481(2) Uani 1 d . . C1 C 0.42922(12) 0.5752(2) 0.38316(9) 0.0459(5) Uani 1 d . . C2 C 0.51455(13) 0.5688(2) 0.42435(9) 0.0516(5) Uani 1 d . . C3 C 0.55346(13) 0.6935(3) 0.44186(12) 0.0629(6) Uani 1 d . . H31 H 0.56247(13) 0.7339(3) 0.40702(12) 0.084 Uiso 1 calc R . H32 H 0.60394(13) 0.6802(3) 0.47098(12) 0.084 Uiso 1 calc R . C4 C 0.50343(14) 0.7810(2) 0.46856(11) 0.0627(6) Uani 1 d . . H41 H 0.50128(14) 0.7467(2) 0.50666(11) 0.083 Uiso 1 calc R . H42 H 0.52795(14) 0.8641(2) 0.47586(11) 0.083 Uiso 1 calc R . C5 C 0.42016(13) 0.7954(2) 0.42744(9) 0.0510(5) Uani 1 d . . H51 H 0.42338(13) 0.8348(2) 0.39015(9) 0.068 Uiso 1 calc R . C6 C 0.38211(13) 0.6650(2) 0.41226(9) 0.0478(5) Uani 1 d . . H61 H 0.32991(13) 0.6758(2) 0.38519(9) 0.064 Uiso 1 calc R . H62 H 0.37681(13) 0.6259(2) 0.44857(9) 0.064 Uiso 1 calc R . O10 O 0.35173(12) 0.4062(2) 0.40571(9) 0.0738(5) Uani 1 d . . O11 O 0.42093(11) 0.36921(15) 0.34049(8) 0.0634(5) Uani 1 d . . C11 C 0.39523(14) 0.4414(2) 0.37761(10) 0.0523(5) Uani 1 d . . C12 C 0.3954(2) 0.2383(3) 0.3353(2) 0.0824(9) Uani 1 d . . H121 H 0.3825(2) 0.2132(3) 0.3713(2) 0.110 Uiso 1 calc R . H122 H 0.3486(2) 0.2298(3) 0.3019(2) 0.110 Uiso 1 calc R . C13 C 0.4545(3) 0.1575(3) 0.3265(2) 0.1166(14) Uani 1 d . . H131 H 0.4329(5) 0.0748(9) 0.3146(14) 0.155 Uiso 1 calc R . H132 H 0.4961(9) 0.1506(24) 0.3630(4) 0.155 Uiso 1 calc R . H133 H 0.4748(13) 0.1921(16) 0.2958(10) 0.155 Uiso 1 calc R . O20 O 0.54338(11) 0.4681(2) 0.44252(8) 0.0703(5) Uani 1 d . . C50 C 0.36997(14) 0.8803(2) 0.45442(9) 0.0527(5) Uani 1 d . . C51 C 0.3394(2) 0.9922(2) 0.42682(12) 0.0650(6) Uani 1 d . . H511 H 0.3493(2) 1.0154(2) 0.39122(12) 0.086 Uiso 1 calc R . C52 C 0.2940(2) 1.0707(3) 0.45114(14) 0.0765(8) Uani 1 d . . H521 H 0.2746(2) 1.1464(3) 0.43199(14) 0.102 Uiso 1 calc R . C53 C 0.2773(2) 1.0382(3) 0.50316(13) 0.0759(8) Uani 1 d . . H531 H 0.2468(2) 1.0910(3) 0.51940(13) 0.101 Uiso 1 calc R . C54 C 0.3065(2) 0.9262(3) 0.53075(13) 0.0835(9) Uani 1 d . . H541 H 0.2953(2) 0.9024(3) 0.56581(13) 0.111 Uiso 1 calc R . C55 C 0.3523(2) 0.8487(3) 0.50689(11) 0.0730(8) Uani 1 d . . H551 H 0.3719(2) 0.7735(3) 0.52640(11) 0.097 Uiso 1 calc R . O2 O 0.26474(10) 0.6237(2) 0.28117(8) 0.0642(5) Uani 1 d . . O3 O 0.32221(9) 0.4853(2) 0.21832(7) 0.0565(4) Uani 1 d . . C31 C 0.3761(2) 0.4492(3) 0.18431(13) 0.0721(7) Uani 1 d . . H311 H 0.4280(2) 0.4355(3) 0.21123(13) 0.096 Uiso 1 calc R . H312 H 0.3792(2) 0.5168(3) 0.15679(13) 0.096 Uiso 1 calc R . C32 C 0.3474(2) 0.3315(3) 0.15078(14) 0.0762(8) Uani 1 d . . H321 H 0.3856(6) 0.3017(11) 0.1320(8) 0.101 Uiso 1 calc R . H322 H 0.2989(7) 0.3485(6) 0.1208(6) 0.101 Uiso 1 calc R . H323 H 0.3390(12) 0.2677(7) 0.1778(2) 0.101 Uiso 1 calc R . O4 O 0.33085(11) 0.7130(2) 0.20341(7) 0.0636(5) Uani 1 d . . C41 C 0.3257(2) 0.8487(3) 0.21458(15) 0.0765(8) Uani 1 d . . H411 H 0.2720(2) 0.8772(3) 0.19856(15) 0.102 Uiso 1 calc R . H412 H 0.3418(2) 0.8648(3) 0.25728(15) 0.102 Uiso 1 calc R . C42 C 0.3760(3) 0.9179(4) 0.1864(2) 0.131(2) Uani 1 d . . H421 H 0.3706(16) 1.0074(4) 0.1920(14) 0.174 Uiso 1 calc R . H422 H 0.3611(14) 0.8990(27) 0.1444(4) 0.174 Uiso 1 calc R . H423 H 0.4295(4) 0.8930(26) 0.2041(11) 0.174 Uiso 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 P1 0.0545(3) 0.0434(3) 0.0447(3) -0.0002(2) 0.0060(2) 0.0017(2) S1 0.0507(3) 0.0467(3) 0.0445(3) 0.0020(2) 0.0095(2) -0.0030(2) C1 0.0492(10) 0.0409(10) 0.0433(9) 0.0038(8) 0.0060(8) 0.0006(9) C2 0.0532(11) 0.0517(12) 0.0463(10) 0.0014(9) 0.0082(9) 0.0044(10) C3 0.0503(12) 0.0608(14) 0.0673(13) -0.0029(11) -0.0001(11) -0.0025(11) C4 0.0599(13) 0.0556(14) 0.0630(13) -0.0096(11) 0.0022(11) -0.0047(11) C5 0.0591(12) 0.0445(11) 0.0456(10) 0.0000(8) 0.0085(9) -0.0010(10) C6 0.0507(11) 0.0459(11) 0.0429(9) -0.0007(8) 0.0069(8) -0.0007(9) O10 0.0914(13) 0.0591(11) 0.0812(12) -0.0041(9) 0.0414(11) -0.0193(10) O11 0.0835(12) 0.0403(8) 0.0705(10) -0.0051(7) 0.0289(9) -0.0065(8) C11 0.0588(12) 0.0430(11) 0.0502(10) 0.0027(9) 0.0077(10) -0.0019(10) C12 0.095(2) 0.0427(13) 0.115(2) -0.0124(14) 0.039(2) -0.0123(14) C13 0.121(3) 0.055(2) 0.189(4) -0.028(2) 0.070(3) -0.007(2) O20 0.0706(11) 0.0587(10) 0.0692(10) 0.0089(8) 0.0000(9) 0.0150(9) C50 0.0623(13) 0.0435(11) 0.0468(10) -0.0017(8) 0.0068(10) -0.0003(10) C51 0.080(2) 0.0484(13) 0.0664(14) 0.0055(11) 0.0198(12) 0.0034(12) C52 0.086(2) 0.0528(14) 0.089(2) 0.0015(13) 0.021(2) 0.0131(14) C53 0.078(2) 0.072(2) 0.079(2) -0.0155(14) 0.0230(15) 0.0082(15) C54 0.110(2) 0.079(2) 0.068(2) -0.0006(14) 0.036(2) 0.014(2) C55 0.105(2) 0.061(2) 0.0570(13) 0.0062(11) 0.0289(14) 0.0186(15) O2 0.0522(9) 0.0747(11) 0.0635(9) -0.0071(8) 0.0128(8) 0.0018(8) O3 0.0615(9) 0.0496(9) 0.0565(8) -0.0084(7) 0.0136(7) -0.0064(7) C31 0.074(2) 0.065(2) 0.081(2) -0.0205(13) 0.0299(14) -0.0124(13) C32 0.084(2) 0.064(2) 0.077(2) -0.0214(14) 0.0171(15) -0.0020(15) O4 0.0855(11) 0.0465(9) 0.0505(8) 0.0056(7) 0.0059(8) 0.0047(8) C41 0.091(2) 0.0444(13) 0.091(2) 0.0091(12) 0.020(2) 0.0104(13) C42 0.190(5) 0.060(2) 0.174(4) 0.002(2) 0.100(4) -0.014(3) _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 P1 O2 1.458(2) . yes P1 O3 1.555(2) . yes P1 O4 1.565(2) . yes P1 S1 2.087(2) . yes S1 C1 1.859(2) . yes C1 C2 1.551(3) . yes C2 C3 1.485(3) . yes C3 C4 1.531(4) . yes C4 C5 1.527(3) . yes C5 C6 1.527(3) . yes C6 C1 1.543(3) . yes C1 C11 1.523(3) . yes C2 O20 1.201(3) . yes C5 C50 1.521(3) . yes C11 O10 1.206(3) . yes C11 O11 1.327(3) . yes O11 C12 1.445(3) . yes C12 C13 1.413(5) . yes O3 C31 1.458(3) . yes C31 C32 1.476(4) . yes O4 C41 1.459(3) . yes C41 C42 1.447(5) . yes C50 C51 1.377(3) . no C51 C52 1.385(4) . no C52 C53 1.372(5) . no C53 C54 1.372(4) . no C54 C55 1.377(4) . no C55 C50 1.388(4) . no C3 H31 0.97 . no C3 H32 0.97 . no C4 H41 0.97 . no C4 H42 0.97 . no C5 H51 0.98 . no C6 H61 0.97 . no C6 H62 0.97 . no C12 H121 0.97 . no C12 H122 0.97 . no C13 H131 0.96 . no C13 H132 0.96 . no C13 H133 0.96 . no C51 H511 0.93 . no C52 H521 0.93 . no C53 H531 0.93 . no C54 H541 0.93 . no C55 H551 0.93 . no C31 H311 0.97 . no C31 H312 0.97 . no C32 H321 0.96 . no C32 H322 0.96 . no C32 H323 0.96 . no C41 H411 0.97 . no C41 H412 0.97 . no C42 H421 0.96 . no C42 H422 0.96 . no C42 H423 0.96 . no 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 O2 P1 O3 111.03(10) . . yes O2 P1 O4 118.79(11) . . yes O3 P1 O4 102.48(10) . . yes O2 P1 S1 113.75(8) . . yes O3 P1 S1 109.84(7) . . yes O4 P1 S1 99.88(8) . . yes C1 S1 P1 103.43(8) . . yes C11 C1 S1 112.39(15) . . yes C2 C1 S1 104.2(2) . . yes C6 C1 S1 113.12(14) . . yes C11 C1 C2 108.0(2) . . yes C11 C1 C6 110.5(2) . . yes C6 C1 C2 108.2(2) . . yes O20 C2 C1 120.1(2) . . yes O20 C2 C3 124.3(2) . . yes C1 C2 C3 115.5(2) . . yes C2 C3 C4 111.3(2) . . yes C3 C4 C5 112.1(2) . . yes C4 C5 C6 110.1(2) . . yes C5 C6 C1 113.1(2) . . yes C11 O11 C12 116.2(2) . . yes O10 C11 O11 124.9(2) . . yes O10 C11 C1 122.6(2) . . yes O11 C11 C1 112.5(2) . . yes C13 C12 O11 110.9(3) . . yes C31 O3 P1 123.5(2) . . yes O3 C31 C32 109.0(2) . . yes C41 O4 P1 120.5(2) . . yes O4 C41 C42 109.4(3) . . yes C50 C5 C4 112.2(2) . . yes C50 C5 C6 110.5(2) . . yes C5 C50 C51 120.6(2) . . no C50 C51 C52 121.2(3) . . no C51 C52 C53 120.8(3) . . no C52 C53 C54 118.7(3) . . no C53 C54 C55 120.5(3) . . no C54 C55 C50 121.6(3) . . no C55 C50 C51 117.3(2) . . no C55 C50 C5 122.1(2) . . no C2 C3 H31 109.37(14) . . no C4 C3 H31 109.37(15) . . no C2 C3 H32 109.37(12) . . no C4 C3 H32 109.37(12) . . no H31 C3 H32 108.0 . . no C5 C4 H41 109.18(14) . . no C3 C4 H41 109.18(15) . . no C5 C4 H42 109.18(13) . . no C3 C4 H42 109.18(14) . . no H41 C4 H42 107.9 . . no C50 C5 H51 107.97(12) . . no C4 C5 H51 107.97(14) . . no C6 C5 H51 107.97(12) . . no C5 C6 H61 108.97(11) . . no C1 C6 H61 108.97(11) . . no C5 C6 H62 108.97(12) . . no C1 C6 H62 108.97(11) . . no H61 C6 H62 107.8 . . no C13 C12 H121 109.5(3) . . no O11 C12 H121 109.5(2) . . no C13 C12 H122 109.5(2) . . no O11 C12 H122 109.5(2) . . no H121 C12 H122 108.0 . . no C12 C13 H131 109.5(2) . . no C12 C13 H132 109.5(3) . . no H131 C13 H132 109.5 . . no C12 C13 H133 109.5(3) . . no H131 C13 H133 109.5 . . no H132 C13 H133 109.5 . . no C50 C51 H511 119.4(2) . . no C52 C51 H511 119.4(2) . . no C53 C52 H521 119.6(2) . . no C51 C52 H521 119.6(2) . . no C54 C53 H531 120.6(2) . . no C52 C53 H531 120.6(2) . . no C53 C54 H541 119.8(2) . . no C55 C54 H541 119.8(2) . . no C54 C55 H551 119.2(2) . . no C50 C55 H551 119.2(2) . . no O3 C31 H311 109.89(14) . . no C32 C31 H311 109.9(2) . . no O3 C31 H312 109.89(15) . . no C32 C31 H312 109.9(2) . . no H311 C31 H312 108.3 . . no C31 C32 H321 109.5(2) . . no C31 C32 H322 109.5(2) . . no H321 C32 H322 109.5 . . no C31 C32 H323 109.5(2) . . no H321 C32 H323 109.5 . . no H322 C32 H323 109.5 . . no C42 C41 H411 109.8(2) . . no O4 C41 H411 109.79(15) . . no C42 C41 H412 109.8(3) . . no O4 C41 H412 109.79(14) . . no H411 C41 H412 108.2 . . no C41 C42 H421 109.5(2) . . no C41 C42 H422 109.5(3) . . no H421 C42 H422 109.5 . . no C41 C42 H423 109.5(3) . . no H421 C42 H423 109.5 . . no H422 C42 H423 109.5 . . no 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 O2 P1 S1 C1 30.23(12) . . . . yes O3 P1 S1 C1 -94.92(10) . . . . yes O4 P1 S1 C1 157.86(10) . . . . yes P1 S1 C1 C11 53.7(2) . . . . yes P1 S1 C1 C6 -72.37(15) . . . . yes P1 S1 C1 C2 170.33(12) . . . . yes S1 C1 C2 O20 -115.4(2) . . . . yes C11 C1 C2 O20 4.3(3) . . . . yes C6 C1 C2 O20 124.0(2) . . . . yes S1 C1 C2 C3 68.6(2) . . . . yes C11 C1 C2 C3 -171.7(2) . . . . yes O20 C2 C3 C4 -123.2(3) . . . . yes C1 C2 C3 C4 52.6(3) . . . . yes C2 C3 C4 C5 -53.3(3) . . . . yes C3 C4 C5 C6 55.4(3) . . . . yes C4 C5 C6 C1 -57.0(2) . . . . yes C5 C6 C1 C2 53.5(2) . . . . yes C6 C1 C2 C3 -52.0(3) . . . . yes S1 C1 C6 C5 -61.4(2) . . . . yes C11 C1 C6 C5 171.6(2) . . . . yes C12 O11 C11 C1 176.4(2) . . . . yes C12 O11 C11 O10 -1.5(4) . . . . yes S1 C1 C11 O10 -144.8(2) . . . . yes C2 C1 C11 O10 100.9(3) . . . . yes C6 C1 C11 O10 -17.3(3) . . . . yes S1 C1 C11 O11 37.3(2) . . . . yes C2 C1 C11 O11 -77.1(2) . . . . yes C6 C1 C11 O11 164.7(2) . . . . yes C11 O11 C12 C13 -145.6(3) . . . . yes S1 P1 O3 C31 -54.5(2) . . . . yes O2 P1 O3 C31 178.8(2) . . . . yes O4 P1 O3 C31 51.0(2) . . . . yes P1 O3 C31 C32 -171.7(2) . . . . yes S1 P1 O4 C41 -75.0(2) . . . . yes O2 P1 O4 C41 49.2(2) . . . . yes O3 P1 O4 C41 171.9(2) . . . . yes P1 O4 C41 C42 144.1(3) . . . . yes C50 C5 C4 C3 178.9(2) . . . . yes C50 C5 C6 C1 178.5(2) . . . . yes C4 C5 C50 C51 117.7(2) . . . . yes C6 C5 C50 C51 -119.0(2) . . . . yes C4 C5 C50 C55 -63.0(3) . . . . no C6 C5 C50 C55 60.3(3) . . . . no C5 C50 C51 C52 -179.6(2) . . . . no C55 C50 C51 C52 1.1(4) . . . . no C50 C51 C52 C53 -0.9(5) . . . . no C51 C52 C53 C54 0.0(5) . . . . no C52 C53 C54 C55 0.7(5) . . . . no C53 C54 C55 C50 -0.5(5) . . . . no C54 C55 C50 C51 -0.4(4) . . . . no C54 C55 C50 C5 -179.7(3) . . . . no loop_ _publ_manuscript_incl_extra_item '_geom_bond_atom_site_label_D' '_geom_bond_atom_site_label_H' '_geom_contact_atom_site_label_A' '_geom_bond_distance_DH' '_geom_contact_distance_HA' '_geom_contact_distance_DA' '_geom_angle_DHA' '_geom_contact_site_symmetry_A' '_geom_extra_tableA_col_1' '_geom_extra_tableA_col_2' '_geom_extra_tableA_col_3' '_geom_extra_tableA_col_4' '_geom_extra_table_head_A' '_geom_extra_tableB_col_1' '_geom_extra_tableB_col_2' '_geom_extra_tableB_col_3' '_geom_extra_tableB_col_4' '_geom_extra_tableB_col_5' '_geom_extra_table_head_B' '_geom_extra_tableC_col_1' '_geom_extra_tableC_col_2' '_geom_extra_tableC_col_3' '_geom_extra_tableC_col_4' '_geom_extra_tableC_col_5' '_geom_extra_table_head_C' loop_ _geom_bond_atom_site_label_D _geom_bond_atom_site_label_H _geom_contact_atom_site_label_A _geom_bond_distance_DH _geom_contact_distance_HA _geom_contact_distance_DA _geom_angle_DHA _geom_contact_site_symmetry_A C4 H41 O20 0.970 2.772 3.584(4) 141.8 5_666 C6 H61 O2 0.970 2.436 3.205(3) 136.0 . C6 H62 O10 0.970 2.508 2.772(3) 95.3 . C6 H62 O20 0.970 2.720 3.555(3) 144.6 5_666 C12 H121 O10 0.970 2.306 2.674(5) 101.6 . C12 H122 O2 0.970 2.617 3.543(4) 160.0 4_545 C31 H312 O4 0.970 2.591 2.959(4) 102.6 . C32 H323 O2 0.960 2.761 3.616(4) 148.7 4_545 C41 H411 O10 0.970 2.795 3.629(4) 144.6 4_555 C41 H411 O2 0.970 2.748 3.326(4) 118.8 4_555 _geom_extra_table_head_A ; Asymmetry parameters (Duax & Norton, 1975) of six-membered ring C1,C2,C3,C4,C5,C6. ; loop_ _geom_extra_tableA_col_1 _geom_extra_tableA_col_2 _geom_extra_tableA_col_3 _geom_extra_tableA_col_4 \DC~s~^(C1)^=\DC~s~^(C4)^ 2.9(5) \DC~2~^(C1\\-C2)^=\DC~2~^(C4\\-C5)^ 2.7(4) \DC~s~^(C2)^=\DC~s~^(C5)^ 1.0(5) \DC~2~^(C2\\-C3)^=\DC~2~^(C5\\-C6)^ 1.6(5) \DC~s~^(C3)^=\DC~s~^(C6)^ 2.8(5) \DC~2~^(C3\\-C4)^=\DC~2~^(C6\\-C1)^ 4.1(5) _geom_extra_table_head_B ; Dihedral angles (\%) between selected weighted least-squares planes (Nardelli, Musatti, Domiano & Andreetti, 1965). Equation of the plane: A*x+B*y+C*z=D ; loop_ _geom_extra_tableB_col_1 _geom_extra_tableB_col_2 _geom_extra_tableB_col_3 _geom_extra_tableB_col_4 _geom_extra_tableB_col_5 'Plane1' C1,C3,C4,C6 ? 'Plane1^\\wedge^Plane2' 48.23(15) 'Plane2' C1,C2,C3 ? 'Plane1^\\wedge^Plane3' 50.34(14) 'Plane3' C4,C5,C6 ? 'Plane2^\\wedge^Plane3' 2.17(20) 'Plane4' C50,C51,C52,C53,C54,C55 ? 'Plane1^\\wedge^Plane4' 88.91(7) ? ? ? 'Plane2^\\wedge^Plane4' 88.84(10) ? ? ? 'Plane3^\\wedge^Plane4' 88.36(10) ? A B C D 'Plane1' 0.1096(12) 0.6364(10) -0.7635(8) -2.1384(131) 'Plane2' -0.5936(13) 0.0207(27) 0.8045(10) 3.9954(132) 'Plane3' -0.6012(12) 0.0570(24) 0.7970(10) 5.3057(132) 'Plane4' -0.6983(6) -0.4834(9) -0.5280(9) -12.3330(72) _geom_extra_table_head_C ; Distances (\%A) of non-hydrogen atoms from weighted least-squares planes 1a and 1b (^*^ indicates atom used to define plane) ; loop_ _geom_extra_tableC_col_1 _geom_extra_tableC_col_2 _geom_extra_tableC_col_3 _geom_extra_tableC_col_4 _geom_extra_tableC_col_5 ? 'Plane1' 'Plane2' 'Plane3' 'Plane4' P1 '2.390(1)' '-1.784(1)' '-2.933(1)' '3.335(1)' S1 '1.717(1)' '-1.678(1)' '-2.841(1)' '1.406(1)' C1 '0.004(2)^*^' '0.000(1)^*^' '-1.193(1)' '1.324(1)' C2 '-0.606(2)' '0.000(1)^*^' '-1.211(1)' '0.000(1)' C3 '-0.006(2)^*^' '0.000(1)^*^' '-1.171(1)' '-1.243(2)' C4 '0.006(2)^*^' '1.134(1)' '0.000(1)^*^' '-1.257(2)' C5 '0.674(2)' '1.112(1)' '0.000(1)^*^' '-0.001(1)' C6 '-0.004(2)^*^' '1.155(1)' '0.000(1)^*^' '1.244(1)' O10 '-1.679(2)' '1.275(1)' '0.026(1)' '2.986(1)' O11 '-0.631(2)' '-0.894(1)' '-2.159(1)' '2.782(1)' C11 '-0.858(2)' '0.207(1)' '-1.031(1)' '2.467(1)' C12 '-1.465(3)' '-0.767(3)' '-2.078(3)' '3.801(3)' C13 '-1.734(5)' '-1.602(5)' '-2.951(5)' '3.541(4)' O20 '-1.546(2)' '0.071(1)' '-1.185(1)' '0.024(1)' C50 '0.664(2)' '2.253(1)' '1.177(1)' '-0.003(1)^*^' C51 '1.845(2)' '1.996(2)' '0.970(2)' '0.007(2)^*^' C52 '1.850(2)' '3.025(2)' '2.033(2)' '-0.003(2)^*^' C53 '0.672(2)' '4.338(2)' '3.328(2)' '-0.004(2)^*^' C54 '-0.513(2)' '4.610(2)' '3.551(2)' '0.005(2)^*^' C55 '-0.517(2)' '3.584(2)' '2.492(2)' '0.000(2)^*^' O2 '1.824(2)' '-0.489(1)' '-1.629(1)' '3.854(1)' O3 '2.130(2)' '-2.506(1)' '-3.699(1)' '4.294(1)' C31 '2.598(2)' '-3.829(2)' '-5.040(2)' '4.052(2)' C32 '2.351(2)' '-4.286(2)' '-5.534(2)' '5.248(2)' O4 '3.936(2)' '-2.875(1)' '-3.981(1)' '3.135(1)' C41 '4.635(3)' '-2.545(3)' '-3.600(3)' '2.429(3)' C42 '5.699(4)' '-3.680(4)' '-4.712(4)' '1.655(4)' #+------------------------------------------------------------ data_Compound9g _database_code_CSD 195723 ##+------------------------------------------------------------- _audit_creation_method SHELXL _chemical_name_systematic ; ? ; _chemical_name_common ; Ethyl 1-[(dineopentoxyphosphoryl)sulfanyl]-3- methyl-2-oxocyclohexanecarboxylate ; _chemical_formula_moiety 'C20 H37 O6 P S' _chemical_formula_structural ? _chemical_formula_analytical ? _chemical_formula_sum 'C20 H37 O6 P S' _chemical_formula_weight 436.53 _chemical_melting_point ? _chemical_compound_source ? loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source 'C' 'C' 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 'H' 'H' 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 'O' 'O' 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 'P' 'P' 0.2955 0.4335 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 'S' 'S' 0.3331 0.5567 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _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, y+1/2, -z+1/2' 'x+1/2, -y+1/2, -z' _cell_length_a 6.075(2) _cell_length_b 19.042(5) _cell_length_c 20.889(8) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 2416.4(14) _cell_formula_units_Z 4 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used 25 _cell_measurement_theta_min 15.44 _cell_measurement_theta_max 30.48 _exptl_crystal_description 'prism' _exptl_crystal_colour 'colourless' _exptl_crystal_size_max 0.50 _exptl_crystal_size_mid 0.30 _exptl_crystal_size_min 0.15 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.200 _exptl_crystal_density_method ? _exptl_crystal_F_000 944 _exptl_absorpt_coefficient_mu 2.069 _exptl_absorpt_correction_type 'empirical' _exptl_absorpt_process_details ; (\y scans; North, Phillips, Mathews, 1968; Frenz, 1986) ; _exptl_absorpt_correction_T_min 0.9142 _exptl_absorpt_correction_T_max 0.9981 _exptl_special_details ; ? ; _diffrn_ambient_temperature 293(2) _diffrn_radiation_wavelength 1.54178 _diffrn_radiation_type CuK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device 'Enraf-Nonius CAD-4' _diffrn_measurement_method '\w/2\q scans' _diffrn_standards_number 3 _diffrn_standards_interval_count ? _diffrn_standards_interval_time 60 _diffrn_standards_decay_% 15.6 _diffrn_reflns_number 11162 _diffrn_reflns_av_R_equivalents 0.0837 _diffrn_reflns_av_sigmaI/netI 0.0828 _diffrn_reflns_limit_h_min 0 _diffrn_reflns_limit_h_max 7 _diffrn_reflns_limit_k_min -23 _diffrn_reflns_limit_k_max 23 _diffrn_reflns_limit_l_min -26 _diffrn_reflns_limit_l_max 26 _diffrn_reflns_theta_min 3.14 _diffrn_reflns_theta_max 74.97 _reflns_number_total 4976 _reflns_number_gt 3385 _reflns_threshold_expression >2sigma(I) #+------------------------------------------------------------ _computing_data_collection ; Enraf--Nonius CAD-4 (Schagen, Straver, van Meurs & Williams, 1989) ; _computing_cell_refinement ; Enraf--Nonius CAD-4 (Schagen, Straver, van Meurs & Williams, 1989) ; _computing_data_reduction ; Enraf--Nonius SDP (Frenz, 1986; North, Phillips & Mathews, 1968) ; _computing_structure_solution ; SHELXS-86 (Sheldrick, 1990) ; _computing_structure_refinement ; SHELXL-93 (Sheldrick, 1993) ; _computing_molecular_graphics ; SHELXTL-Plus - XP (Sheldrick, 1991) ; _computing_publication_material ; CSU (Vickovic, 1988) ; #+------------------------------------------------------------ _refine_special_details ; Refinement on F^2^ for ALL reflections except for 517 with very negative F^2^ or flagged by the user for potential systematic errors. Weighted R-factors wR and all goodnesses 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 observed criterion of F^2^ > 2sigma(F^2^) is used only for calculating _R_factor_obs 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. Refinement of racemic twinning. Hydrogen atoms were placed geometrically at idealised positions, and set as riding with fixed thermal parameters equal to 1.33 times of the equivalent isotropic thermal parameter of the parent-atom. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme 'calc' _refine_ls_weighting_details 'w=1/[\s^2^(Fo^2^)+(0.0539P)^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 'constr' _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 0.48(3) _refine_ls_number_reflns 4459 _refine_ls_number_parameters 262 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0924 _refine_ls_R_factor_gt 0.0503 _refine_ls_wR_factor_all 0.1368 _refine_ls_wR_factor_ref 0.1136 _refine_ls_goodness_of_fit_all 1.042 _refine_ls_goodness_of_fit_ref 1.107 _refine_ls_restrained_S_all 1.089 _refine_ls_restrained_S_obs 1.107 _refine_ls_shift/su_max 0.001 _refine_ls_shift/esd_mean 0.000 _refine_diff_density_max 0.233 _refine_diff_density_min -0.261 _refine_diff_density_rms 0.044 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_thermal_displace_type _atom_site_occupancy _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_group P1 P 0.35856(14) 0.57196(5) 0.76580(4) 0.0501(2) Uani 1 d . . S1 S 0.19304(13) 0.50331(5) 0.82726(4) 0.0509(2) Uani 1 d . . C1 C 0.3360(6) 0.5185(2) 0.9040(2) 0.0506(8) Uani 1 d . . C2 C 0.2206(6) 0.4688(2) 0.9518(2) 0.0542(8) Uani 1 d . . C3 C 0.2597(6) 0.3917(2) 0.9432(2) 0.0575(10) Uani 1 d . . H31 H 0.1988(6) 0.3782(2) 0.9015(2) 0.076 Uiso 1 calc R . C4 C 0.5081(7) 0.3776(2) 0.9413(2) 0.0670(11) Uani 1 d . . H41 H 0.5716(7) 0.3883(2) 0.9828(2) 0.089 Uiso 1 calc R . H42 H 0.5336(7) 0.3283(2) 0.9324(2) 0.089 Uiso 1 calc R . C5 C 0.6200(6) 0.4218(2) 0.8905(2) 0.0647(10) Uani 1 d . . H51 H 0.7768(6) 0.4122(2) 0.8907(2) 0.086 Uiso 1 calc R . H52 H 0.5631(6) 0.4091(2) 0.8487(2) 0.086 Uiso 1 calc R . C6 C 0.5826(5) 0.4992(2) 0.9017(2) 0.0583(9) Uani 1 d . . H61 H 0.6530(5) 0.5257(2) 0.8677(2) 0.078 Uiso 1 calc R . H62 H 0.6511(5) 0.5126(2) 0.9418(2) 0.078 Uiso 1 calc R . O10 O 0.4384(7) 0.6186(2) 0.9656(2) 0.1058(12) Uani 1 d . . O11 O 0.1242(5) 0.62293(13) 0.91045(14) 0.0741(8) Uani 1 d . . C11 C 0.3080(8) 0.5931(2) 0.9300(2) 0.0656(10) Uani 1 d . . C12 C 0.0879(12) 0.6932(3) 0.9360(3) 0.125(3) Uani 1 d . . H121 H 0.0813(12) 0.6906(3) 0.9823(3) 0.166 Uiso 1 calc R . H122 H 0.2120(12) 0.7227(3) 0.9246(3) 0.166 Uiso 1 calc R . C13 C -0.0955(13) 0.7227(4) 0.9145(3) 0.165(4) Uani 1 d . . H131 H -0.1178(54) 0.7668(15) 0.9357(22) 0.220 Uiso 1 calc R . H132 H -0.2180(19) 0.6923(15) 0.9230(25) 0.220 Uiso 1 calc R . H133 H -0.0833(41) 0.7303(29) 0.8692(6) 0.220 Uiso 1 calc R . O20 O 0.1139(6) 0.4918(2) 0.99477(15) 0.0989(11) Uani 1 d . . C30 C 0.1419(8) 0.3483(2) 0.9944(2) 0.0775(12) Uani 1 d . . H301 H -0.0142(8) 0.3552(12) 0.9907(9) 0.103 Uiso 1 calc R . H302 H 0.1900(35) 0.3630(10) 1.0361(2) 0.103 Uiso 1 calc R . H303 H 0.1758(37) 0.2995(3) 0.9885(8) 0.103 Uiso 1 calc R . O2 O 0.4835(4) 0.62537(13) 0.80006(13) 0.0629(7) Uani 1 d . . O3 O 0.1717(4) 0.59732(12) 0.71942(10) 0.0574(6) Uani 1 d . . C31 C 0.0123(6) 0.6497(2) 0.7428(2) 0.0632(10) Uani 1 d . . H311 H 0.0732(6) 0.6741(2) 0.7795(2) 0.084 Uiso 1 calc R . H312 H -0.1216(6) 0.6262(2) 0.7563(2) 0.084 Uiso 1 calc R . C32 C -0.0404(6) 0.7020(2) 0.6903(2) 0.0510(8) Uani 1 d . . C33 C 0.1699(7) 0.7381(2) 0.6671(2) 0.0779(12) Uani 1 d . . H331 H 0.2589(23) 0.7050(4) 0.6441(12) 0.104 Uiso 1 calc R . H332 H 0.2507(24) 0.7555(13) 0.7033(2) 0.104 Uiso 1 calc R . H333 H 0.1321(7) 0.7765(10) 0.6394(11) 0.104 Uiso 1 calc R . C34 C -0.1531(8) 0.6664(2) 0.6346(2) 0.0776(12) Uani 1 d . . H341 H -0.2833(28) 0.6429(13) 0.6495(3) 0.103 Uiso 1 calc R . H342 H -0.0548(19) 0.6327(11) 0.6158(9) 0.103 Uiso 1 calc R . H343 H -0.1927(43) 0.7009(3) 0.6031(7) 0.103 Uiso 1 calc R . C35 C -0.1949(7) 0.7564(2) 0.7199(2) 0.0735(11) Uani 1 d . . H351 H -0.3216(24) 0.7332(2) 0.7373(13) 0.098 Uiso 1 calc R . H352 H -0.2409(39) 0.7891(9) 0.6875(4) 0.098 Uiso 1 calc R . H353 H -0.1192(17) 0.7812(11) 0.7533(10) 0.098 Uiso 1 calc R . O4 O 0.5108(4) 0.52827(12) 0.72102(11) 0.0593(6) Uani 1 d . . C41 C 0.4280(6) 0.4759(2) 0.6781(2) 0.0716(11) Uani 1 d . . H411 H 0.3557(6) 0.4986(2) 0.6423(2) 0.095 Uiso 1 calc R . H412 H 0.3195(6) 0.4474(2) 0.7002(2) 0.095 Uiso 1 calc R . C42 C 0.6135(6) 0.4286(2) 0.6532(2) 0.0594(9) Uani 1 d . . C43 C 0.7786(8) 0.4714(3) 0.6151(2) 0.0882(14) Uani 1 d . . H431 H 0.8807(32) 0.4404(3) 0.5944(12) 0.117 Uiso 1 calc R . H432 H 0.8570(37) 0.5022(12) 0.6434(3) 0.117 Uiso 1 calc R . H433 H 0.7025(9) 0.4987(13) 0.5834(10) 0.117 Uiso 1 calc R . C44 C 0.7304(11) 0.3942(3) 0.7089(2) 0.114(2) Uani 1 d . . H441 H 0.8406(48) 0.3625(17) 0.6930(2) 0.152 Uiso 1 calc R . H442 H 0.6258(16) 0.3685(17) 0.7342(11) 0.152 Uiso 1 calc R . H443 H 0.7989(56) 0.4296(3) 0.7348(11) 0.152 Uiso 1 calc R . C45 C 0.5047(11) 0.3751(3) 0.6113(3) 0.106(2) Uani 1 d . . H451 H 0.6150(11) 0.3466(12) 0.5911(13) 0.142 Uiso 1 calc R . H452 H 0.4188(48) 0.3985(3) 0.5791(11) 0.142 Uiso 1 calc R . H453 H 0.4104(46) 0.3459(12) 0.6368(4) 0.142 Uiso 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 P1 0.0465(4) 0.0523(4) 0.0516(4) 0.0063(4) 0.0057(4) 0.0056(4) S1 0.0468(4) 0.0565(4) 0.0493(4) 0.0046(4) -0.0043(4) -0.0043(4) C1 0.047(2) 0.055(2) 0.050(2) -0.0009(14) -0.003(2) 0.001(2) C2 0.050(2) 0.066(2) 0.046(2) 0.002(2) 0.006(2) 0.008(2) C3 0.060(2) 0.060(2) 0.052(2) 0.007(2) 0.000(2) 0.007(2) C4 0.059(2) 0.068(2) 0.074(3) 0.015(2) 0.002(2) 0.019(2) C5 0.050(2) 0.078(3) 0.066(2) 0.009(2) 0.006(2) 0.015(2) C6 0.044(2) 0.071(2) 0.060(2) 0.008(2) -0.0087(15) -0.001(2) O10 0.128(3) 0.084(2) 0.106(2) -0.033(2) -0.041(2) -0.001(2) O11 0.089(2) 0.0566(14) 0.076(2) -0.0108(13) -0.002(2) 0.028(2) C11 0.081(3) 0.057(2) 0.060(2) -0.003(2) -0.011(2) 0.006(2) C12 0.187(7) 0.073(3) 0.115(4) -0.020(3) -0.022(5) 0.063(4) C13 0.222(9) 0.142(6) 0.132(6) -0.056(5) -0.023(6) 0.107(6) O20 0.130(3) 0.085(2) 0.083(2) 0.006(2) 0.051(2) 0.028(2) C30 0.075(3) 0.082(3) 0.075(3) 0.027(2) 0.003(2) -0.001(2) O2 0.0574(14) 0.0611(15) 0.070(2) 0.0032(13) 0.0011(13) -0.0102(13) O3 0.0625(14) 0.0594(12) 0.0502(12) 0.0085(10) 0.0029(12) 0.0190(13) C31 0.059(2) 0.069(2) 0.061(2) 0.011(2) 0.011(2) 0.019(2) C32 0.045(2) 0.049(2) 0.059(2) 0.0087(15) -0.002(2) 0.0000(15) C33 0.069(3) 0.064(2) 0.101(3) -0.002(2) 0.015(3) -0.012(2) C34 0.082(3) 0.076(3) 0.075(3) 0.008(2) -0.025(3) -0.005(3) C35 0.063(2) 0.061(2) 0.096(3) 0.008(2) -0.001(2) 0.012(2) O4 0.0533(13) 0.0604(14) 0.0641(15) -0.0071(12) 0.0082(13) 0.0018(11) C41 0.060(2) 0.069(2) 0.085(3) -0.007(2) -0.014(2) 0.001(2) C42 0.074(2) 0.051(2) 0.053(2) -0.002(2) -0.006(2) 0.008(2) C43 0.079(3) 0.100(3) 0.086(3) -0.013(3) 0.016(3) 0.006(3) C44 0.162(6) 0.098(4) 0.083(3) 0.013(3) -0.025(4) 0.057(4) C45 0.124(4) 0.080(3) 0.115(4) -0.027(3) -0.006(4) -0.003(3) _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 P1 O2 1.457(3) . yes P1 O3 1.569(2) . yes P1 O4 1.557(2) . yes P1 S1 2.0900(12) . yes S1 C1 1.846(3) . yes C1 C2 1.544(5) . yes C2 C3 1.498(5) . yes C3 C4 1.533(5) . yes C4 C5 1.516(5) . yes C5 C6 1.509(5) . yes C6 C1 1.543(4) . yes C1 C11 1.531(5) . yes C2 O20 1.190(4) . yes C3 C30 1.529(5) . yes C11 O10 1.189(5) . yes C11 O11 1.318(5) . yes O11 C12 1.457(5) . yes C12 C13 1.326(8) . yes O3 C31 1.473(4) . yes C31 C32 1.517(5) . yes O4 C41 1.432(4) . yes C41 C42 1.534(5) . yes C32 C34 1.510(5) . no C32 C35 1.529(5) . no C32 C33 1.530(5) . no C42 C45 1.496(6) . no C42 C44 1.513(5) . no C42 C43 1.517(6) . no C3 H31 0.98 . no C4 H41 0.97 . no C4 H42 0.97 . no C5 H51 0.97 . no C5 H52 0.97 . no C6 H61 0.97 . no C6 H62 0.97 . no C12 H121 0.97 . no C12 H122 0.97 . no C13 H131 0.96 . no C13 H132 0.96 . no C13 H133 0.96 . no C30 H301 0.96 . no C30 H302 0.96 . no C30 H303 0.96 . no C31 H311 0.97 . no C31 H312 0.97 . no C33 H331 0.96 . no C33 H332 0.96 . no C33 H333 0.96 . no C34 H341 0.96 . no C34 H342 0.96 . no C34 H343 0.96 . no C35 H351 0.96 . no C35 H352 0.96 . no C35 H353 0.96 . no C41 H411 0.97 . no C41 H412 0.97 . no C43 H431 0.96 . no C43 H432 0.96 . no C43 H433 0.96 . no C44 H441 0.96 . no C44 H442 0.96 . no C44 H443 0.96 . no C45 H451 0.96 . no C45 H452 0.96 . no C45 H453 0.96 . no 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 O2 P1 O3 117.75(15) . . yes O2 P1 O4 111.0(2) . . yes O3 P1 O4 102.91(13) . . yes O2 P1 S1 112.68(11) . . yes O3 P1 S1 102.93(10) . . yes O4 P1 S1 108.71(10) . . yes C1 S1 P1 102.07(12) . . yes C11 C1 S1 113.7(2) . . yes C2 C1 S1 104.6(2) . . yes C6 C1 S1 113.1(2) . . yes C11 C1 C2 106.8(3) . . yes C11 C1 C6 109.9(3) . . yes C6 C1 C2 108.3(3) . . yes O20 C2 C1 120.6(3) . . yes O20 C2 C3 122.5(4) . . yes C1 C2 C3 116.8(3) . . yes C2 C3 C4 109.3(3) . . yes C3 C4 C5 111.3(3) . . yes C4 C5 C6 111.4(3) . . yes C5 C6 C1 112.5(3) . . yes C11 O11 C12 114.2(4) . . yes O10 C11 O11 125.7(4) . . yes O10 C11 C1 121.7(4) . . yes O11 C11 C1 112.5(3) . . yes C13 C12 O11 113.1(6) . . yes C31 O3 P1 118.6(2) . . yes O3 C31 C32 110.1(3) . . yes C41 O4 P1 122.7(2) . . yes O4 C41 C42 111.3(3) . . yes C30 C3 C2 111.8(3) . . yes C30 C3 C4 112.6(3) . . yes C31 C32 C33 110.4(3) . . no C31 C32 C34 111.0(3) . . no C31 C32 C35 106.4(3) . . no C33 C32 C34 109.7(3) . . no C34 C32 C35 109.8(3) . . no C35 C32 C33 109.6(3) . . no C41 C42 C43 110.4(3) . . no C41 C42 C44 109.8(3) . . no C41 C42 C45 105.9(4) . . no C43 C42 C44 109.0(4) . . no C44 C42 C45 111.2(4) . . no C45 C42 C43 110.6(4) . . no C2 C3 H31 107.6(2) . . no C30 C3 H31 107.6(2) . . no C4 C3 H31 107.6(2) . . no C5 C4 H41 109.4(2) . . no C3 C4 H41 109.4(2) . . no C5 C4 H42 109.4(2) . . no C3 C4 H42 109.4(2) . . no H41 C4 H42 108.0 . . no C6 C5 H51 109.3(2) . . no C4 C5 H51 109.3(2) . . no C6 C5 H52 109.3(2) . . no C4 C5 H52 109.3(2) . . no H51 C5 H52 108.0 . . no C5 C6 H61 109.1(2) . . no C1 C6 H61 109.1(2) . . no C5 C6 H62 109.1(2) . . no C1 C6 H62 109.1(2) . . no H61 C6 H62 107.8 . . no C13 C12 H121 109.0(4) . . no O11 C12 H121 109.0(3) . . no C13 C12 H122 109.0(5) . . no O11 C12 H122 109.0(3) . . no H121 C12 H122 107.8 . . no C12 C13 H131 109.5(4) . . no C12 C13 H132 109.5(5) . . no H131 C13 H132 109.47(5) . . no C12 C13 H133 109.5(4) . . no H131 C13 H133 109.5 . . no H132 C13 H133 109.47(7) . . no C3 C30 H301 109.5(2) . . no C3 C30 H302 109.5(2) . . no H301 C30 H302 109.5 . . no C3 C30 H303 109.5(2) . . no H301 C30 H303 109.5 . . no H302 C30 H303 109.5 . . no O3 C31 H311 109.6(2) . . no C32 C31 H311 109.6(2) . . no O3 C31 H312 109.6(2) . . no C32 C31 H312 109.6(2) . . no H311 C31 H312 108.2 . . no C32 C33 H331 109.5(2) . . no C32 C33 H332 109.5(2) . . no H331 C33 H332 109.5 . . no C32 C33 H333 109.5(2) . . no H331 C33 H333 109.5 . . no H332 C33 H333 109.5 . . no C32 C34 H341 109.5(2) . . no C32 C34 H342 109.5(2) . . no H341 C34 H342 109.5 . . no C32 C34 H343 109.5(2) . . no H341 C34 H343 109.5 . . no H342 C34 H343 109.5 . . no C32 C35 H351 109.5(2) . . no C32 C35 H352 109.5(2) . . no H351 C35 H352 109.5 . . no C32 C35 H353 109.5(2) . . no H351 C35 H353 109.5 . . no H352 C35 H353 109.5 . . no O4 C41 H411 109.4(2) . . no C42 C41 H411 109.4(2) . . no O4 C41 H412 109.4(2) . . no C42 C41 H412 109.4(2) . . no H411 C41 H412 108.0 . . no C42 C43 H431 109.5(2) . . no C42 C43 H432 109.5(2) . . no H431 C43 H432 109.5 . . no C42 C43 H433 109.5(2) . . no H431 C43 H433 109.5 . . no H432 C43 H433 109.5 . . no C42 C44 H441 109.5(3) . . no C42 C44 H442 109.5(3) . . no H441 C44 H442 109.5 . . no C42 C44 H443 109.5(3) . . no H441 C44 H443 109.5 . . no H442 C44 H443 109.5 . . no C42 C45 H451 109.5(3) . . no C42 C45 H452 109.5(3) . . no H451 C45 H452 109.5 . . no C42 C45 H453 109.5(3) . . no H451 C45 H453 109.5 . . no H452 C45 H453 109.5 . . no 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 O2 P1 S1 C1 -17.3(2) . . . . yes O3 P1 S1 C1 -145.11(14) . . . . yes O4 P1 S1 C1 106.25(15) . . . . yes P1 S1 C1 C11 64.0(3) . . . . yes P1 S1 C1 C2 -179.9(2) . . . . yes P1 S1 C1 C6 -62.2(3) . . . . yes S1 C1 C2 O20 -113.2(4) . . . . yes C11 C1 C2 O20 7.7(5) . . . . yes C6 C1 C2 O20 126.0(4) . . . . yes S1 C1 C2 C3 69.9(3) . . . . yes C11 C1 C2 C3 -169.3(3) . . . . yes O20 C2 C3 C4 -123.8(4) . . . . yes C1 C2 C3 C4 53.1(4) . . . . yes C2 C3 C4 C5 -54.7(5) . . . . yes C3 C4 C5 C6 58.3(5) . . . . yes C4 C5 C6 C1 -57.2(4) . . . . yes C5 C6 C1 C2 51.1(4) . . . . yes C6 C1 C2 C3 -51.0(4) . . . . yes S1 C1 C6 C5 -64.3(4) . . . . yes C11 C1 C6 C5 167.5(3) . . . . yes C12 O11 C11 C1 178.0(4) . . . . yes C12 O11 C11 O10 0.4(7) . . . . yes S1 C1 C11 O10 -155.5(4) . . . . yes C2 C1 C11 O10 89.7(5) . . . . yes C6 C1 C11 O10 -27.6(5) . . . . yes S1 C1 C11 O11 26.8(4) . . . . yes C2 C1 C11 O11 -88.0(4) . . . . yes C6 C1 C11 O11 154.7(3) . . . . yes S1 P1 O3 C31 76.2(3) . . . . yes O2 P1 O3 C31 -48.4(3) . . . . yes O4 P1 O3 C31 -170.8(2) . . . . yes P1 O3 C31 C32 140.7(3) . . . . yes S1 P1 O4 C41 60.4(3) . . . . yes O2 P1 O4 C41 -175.1(3) . . . . yes O3 P1 O4 C41 -48.2(3) . . . . yes P1 O4 C41 C42 -165.3(2) . . . . yes C30 C3 C2 C1 178.5(3) . . . . yes C30 C3 C4 C5 -179.6(4) . . . . yes C30 C3 C2 O20 1.6(6) . . . . yes C11 O11 C12 C13 178.6(6) . . . . no O3 C31 C32 C33 -57.8(4) . . . . no O3 C31 C32 C34 64.0(4) . . . . no O3 C31 C32 C35 -176.6(3) . . . . no O4 C41 C42 C43 -62.4(5) . . . . no O4 C41 C42 C44 57.8(5) . . . . no O4 C41 C42 C45 177.9(4) . . . . no loop_ _publ_manuscript_incl_extra_item '_geom_bond_atom_site_label_D' '_geom_bond_atom_site_label_H' '_geom_contact_atom_site_label_A' '_geom_bond_distance_DH' '_geom_contact_distance_HA' '_geom_contact_distance_DA' '_geom_angle_DHA' '_geom_contact_site_symmetry_A' '_geom_extra_tableA_col_1' '_geom_extra_tableA_col_2' '_geom_extra_tableA_col_3' '_geom_extra_tableA_col_4' '_geom_extra_table_head_A' '_geom_extra_tableB_col_1' '_geom_extra_tableB_col_2' '_geom_extra_tableB_col_3' '_geom_extra_tableB_col_4' '_geom_extra_tableB_col_5' '_geom_extra_table_head_B' '_geom_extra_tableC_col_1' '_geom_extra_tableC_col_2' '_geom_extra_tableC_col_3' '_geom_extra_tableC_col_4' '_geom_extra_table_head_C' loop_ _geom_bond_atom_site_label_D _geom_bond_atom_site_label_H _geom_contact_atom_site_label_A _geom_bond_distance_DH _geom_contact_distance_HA _geom_contact_distance_DA _geom_angle_DHA _geom_contact_site_symmetry_A C6 H61 O2 0.970 2.580 3.262(4) 127.4 . C6 H62 O10 0.970 2.448 2.778(6) 99.5 . C12 H121 O10 0.970 2.590 2.633(8) 81.8 . C12 H122 O10 0.970 2.559 2.633(8) 83.6 . C13 H132 O10 0.960 2.668 3.617(9) 170.4 1_455 C30 H301 O20 0.960 2.717 2.738(5) 81.1 . C30 H302 O20 0.960 2.641 2.738(5) 85.5 . C31 H311 O2 0.970 2.694 3.137(5) 108.3 . C31 H312 O2 0.970 2.568 3.459(5) 152.8 1_455 C33 H331 O3 0.960 2.638 2.895(4) 95.7 . C34 H342 O3 0.960 2.652 2.960(5) 99.1 . C35 H351 O2 0.960 2.708 3.584(5) 152.1 1_455 C41 H411 O3 0.970 2.716 2.918(5) 92.1 . C43 H432 O4 0.960 2.701 2.952(5) 95.5 . C43 H433 O20 0.960 2.674 3.534(6) 149.3 2_564 C44 H443 O4 0.960 2.584 2.892(6) 98.9 . C45 H452 O20 0.960 2.739 3.587(7) 147.5 2_564 _geom_extra_table_head_A ; Asymmetry parameters (Duax & Norton, 1975) of six-membered ring C1,C2,C3,C4,C5,C6. ; loop_ _geom_extra_tableA_col_1 _geom_extra_tableA_col_2 _geom_extra_tableA_col_3 _geom_extra_tableA_col_4 \DC~s~^(C1)^=\DC~s~^(C4)^ 3.2(7) \DC~2~^(C1\\-C2)^=\DC~2~^(C4\\-C5)^ 2.3(9) \DC~s~^(C2)^=\DC~s~^(C5)^ 2.5(8) \DC~2~^(C2\\-C3)^=\DC~2~^(C5\\-C6)^ 5.7(8) \DC~s~^(C3)^=\DC~s~^(C6)^ 5.6(8) \DC~2~^(C3\\-C4)^=\DC~2~^(C6\\-C1)^ 5.7(9) _geom_extra_table_head_B ; Dihedral angles (\%) between selected weighted least-squares planes (Nardelli, Musatti, Domiano & Andreetti, 1965). Equation of the plane: A*x+B*y+C*z=D ; loop_ _geom_extra_tableB_col_1 _geom_extra_tableB_col_2 _geom_extra_tableB_col_3 _geom_extra_tableB_col_4 _geom_extra_tableB_col_5 'Plane1' C1,C3,C4,C6 ? 'Plane1^\\wedge^Plane2' 48.30(26) 'Plane2' C1,C2,C3 ? 'Plane1^\\wedge^Plane3' 51.74(28) 'Plane3' C4,C5,C6 ? 'Plane2^\\wedge^Plane3' 3.46(35) ? A B C D 'Plane1' -0.0932(26) -0.3110(16) -0.9458(5) -21.1123(40) 'Plane2' 0.7925(36) 0.0538(29) 0.6075(46) 13.6214(1013) 'Plane3' 0.8273(31) 0.0385(28) 0.5604(45) 13.8514(897) _geom_extra_table_head_C ; Distances (\%A) of non-hydrogen atoms from weighted least-squares planes 1a and 1b (^*^ indicates atom used to define plane) ; loop_ _geom_extra_tableC_col_1 _geom_extra_tableC_col_2 _geom_extra_tableC_col_3 _geom_extra_tableC_col_4 ? 'Plane1' 'Plane2' 'Plane3' P1 '2.391(1)' '-1.590(1)' '-2.663(1)' S1 '1.677(1)' '-1.677(1)' '-2.826(1)' C1 '-0.010(4)^*^' '0.000(3)^*^' '-1.198(3)' C2 '-0.595(4)' '0.000(3)^*^' '-1.255(3)' C3 '0.010(4)^*^' '0.000(3)^*^' '-1.216(3)' C4 '-0.010(4)^*^' '1.157(4)' '0.000(4)^*^' C5 '0.669(4)' '1.097(3)' '0.000(3)^*^' C6 '0.010(4)^*^' '1.138(3)' '0.000(3)^*^' O10 '-1.878(4)' '1.377(4)' '0.111(4)' O11 '-0.637(2)' '-0.830(2)' '-2.110(2)' C11 '-0.952(4)' '0.273(4)' '-0.979(4)' C12 '-1.536(6)' '-0.609(6)' '-1.942(6)' C13 '-1.182(6)' '-1.735(7)' '-3.094(7)' O20 '-1.520(4)' '0.056(3)' '-1.271(3)' C30 '-0.678(4)' '0.038(4)' '-1.240(4)' O2 '1.326(2)' '-0.499(2)' '-1.595(2)' O3 '3.264(2)' '-3.053(2)' '-4.127(2)' C31 '2.581(4)' '-3.469(4)' '-4.616(4)' C32 '3.339(4)' '-4.336(3)' '-5.457(3)' C33 '3.464(4)' '-3.581(4)' '-4.645(4)' C34 '4.714(4)' '-5.622(4)' '-6.702(4)' C35 '2.519(4)' '-4.648(4)' '-5.847(4)' O4 '3.449(2)' '-1.471(2)' '-2.455(2)' C41 '4.654(4)' '-2.467(4)' '-3.412(4)' C42 '5.321(4)' '-1.939(4)' '-2.806(4)' C43 '5.726(4)' '-1.584(4)' '-2.391(4)' C44 '4.358(4)' '-0.705(5)' '-1.592(6)' C45 '6.527(6)' '-3.049(6)' '-3.883(6)' #+------------------------------------------------------------ data_Compound28d _database_code_CSD 195724 ##+------------------------------------------------------------- _audit_creation_method SHELXL _chemical_name_systematic: ; Ethyl 2-[(diethoxyphosphoryl)oxy]-5-phenyl-1- (methylsylfinyl)cyclohexanecarboxylate ; _chemical_name_common sulphoxide _chemical_formula_moiety 'C20 H31 O7 P S' _chemical_formula_structural ? _chemical_formula_analytical ? _chemical_formula_sum 'C20 H31 O7 P S' _chemical_formula_weight 446.48 _chemical_melting_point ? _chemical_compound_source ? loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source 'C' 'C' 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 'H' 'H' 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 'O' 'O' 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 'P' 'P' 0.2955 0.4335 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 'S' 'S' 0.3331 0.5567 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M 'P 21/n' _symmetry_space_group_name_Hall '-P 2yn' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, y+1/2, -z+1/2' '-x, -y, -z' 'x-1/2, -y-1/2, z-1/2' _cell_length_a 13.705(3) _cell_length_b 11.378(2) _cell_length_c 15.252(3) _cell_angle_alpha 90.00 _cell_angle_beta 103.02(3) _cell_angle_gamma 90.00 _cell_volume 2317.2(8) _cell_formula_units_Z 4 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used 25 _cell_measurement_theta_min 20.38 _cell_measurement_theta_max 27.55 _exptl_crystal_description 'monoclinic prism' _exptl_crystal_colour 'colourless' _exptl_crystal_size_max 0.40 _exptl_crystal_size_mid 0.24 _exptl_crystal_size_min 0.20 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.280 _exptl_crystal_density_method ? _exptl_crystal_F_000 952 _exptl_absorpt_coefficient_mu 2.209 _exptl_absorpt_correction_type 'empirical' _exptl_absorpt_process_details ; (\y scans; North, Phillips, Mathews, 1968; Frenz, 1986) ; _exptl_absorpt_correction_T_min 0.9049 _exptl_absorpt_correction_T_max 0.9993 _exptl_special_details ; ? ; _diffrn_ambient_temperature 293(2) _diffrn_radiation_wavelength 1.54178 _diffrn_radiation_type CuK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device 'Enraf-Nonius CAD-4' _diffrn_measurement_method '\w/2\q scans' _diffrn_standards_number 3 _diffrn_standards_interval_count ? _diffrn_standards_interval_time 60 _diffrn_standards_decay_% 27.9 _diffrn_reflns_number 9532 _diffrn_reflns_av_R_equivalents 0.0384 _diffrn_reflns_av_sigmaI/netI 0.0329 _diffrn_reflns_limit_h_min -16 _diffrn_reflns_limit_h_max 17 _diffrn_reflns_limit_k_min -13 _diffrn_reflns_limit_k_max 14 _diffrn_reflns_limit_l_min -19 _diffrn_reflns_limit_l_max 0 _diffrn_reflns_theta_min 3.92 _diffrn_reflns_theta_max 74.82 _reflns_number_total 4757 _reflns_number_gt 4089 _reflns_threshold_expression >2sigma(I) #+------------------------------------------------------------ _computing_data_collection ; Enraf--Nonius CAD-4 (Schagen, Straver, van Meurs & Williams, 1989) ; _computing_cell_refinement ; Enraf--Nonius CAD-4 (Schagen, Straver, van Meurs & Williams, 1989) ; _computing_data_reduction ; Enraf--Nonius SDP (Frenz, 1986; North, Phillips & Mathews, 1968) ; _computing_structure_solution ; SHELXS-86 (Sheldrick, 1990) ; _computing_structure_refinement ; SHELXL-93 (Sheldrick, 1993) ; _computing_molecular_graphics ; SHELXTL-Plus - XP (Sheldrick, 1991) ; _computing_publication_material ; CSU (Vickovic, 1988) ; #+------------------------------------------------------------ _refine_special_details ; Refinement on F^2^ for ALL reflections except for 180 with very negative F^2^ or flagged by the user for potential systematic errors. Weighted R-factors wR and all goodnesses 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 observed criterion of F^2^ > 2sigma(F^2^) is used only for calculating _R_factor_obs 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. Hydrogen atoms were placed geometrically at idealised positions, and set as riding with fixed thermal parameters equal to 1.33 times of the equivalent isotropic thermal parameter of the parent-atom. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme 'calc' _refine_ls_weighting_details 'w=1/[\s^2^(Fo^2^)+(0.1030P)^2^+0.5780P] 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 SHELXL _refine_ls_extinction_coef 0.0017(3) _refine_ls_extinction_expression 'Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^' _refine_ls_number_reflns 4577 _refine_ls_number_parameters 267 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0635 _refine_ls_R_factor_gt 0.0570 _refine_ls_wR_factor_all 0.1734 _refine_ls_wR_factor_ref 0.1641 _refine_ls_goodness_of_fit_all 1.044 _refine_ls_goodness_of_fit_ref 1.073 _refine_ls_restrained_S_all 1.047 _refine_ls_restrained_S_obs 1.073 _refine_ls_shift/su_max -0.001 _refine_ls_shift/esd_mean 0.000 _refine_diff_density_max 0.518 _refine_diff_density_min -0.345 _refine_diff_density_rms 0.054 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_thermal_displace_type _atom_site_occupancy _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_group P1 P 1.02200(4) -0.04014(6) 0.31745(4) 0.0657(2) Uani 1 d . . S1 S 0.73854(4) 0.11800(4) 0.17118(4) 0.0576(2) Uani 1 d . . C1 C 0.73983(14) -0.0367(2) 0.21759(13) 0.0477(4) Uani 1 d . . C2 C 0.82642(15) -0.0414(2) 0.30112(14) 0.0534(5) Uani 1 d . . H21 H 0.84058(15) -0.1238(2) 0.31803(14) 0.071 Uiso 1 calc R . C3 C 0.8056(2) 0.0244(2) 0.38136(15) 0.0669(6) Uani 1 d . . H31 H 0.8001(2) 0.1077(2) 0.36781(15) 0.089 Uiso 1 calc R . H32 H 0.8612(2) 0.0133(2) 0.43271(15) 0.089 Uiso 1 calc R . C4 C 0.7093(2) -0.0181(3) 0.4052(2) 0.0731(7) Uani 1 d . . H41 H 0.7158(2) -0.1004(3) 0.4220(2) 0.097 Uiso 1 calc R . H42 H 0.6974(2) 0.0262(3) 0.4561(2) 0.097 Uiso 1 calc R . C5 C 0.6216(2) -0.0021(2) 0.32483(15) 0.0603(5) Uani 1 d . . H51 H 0.6180(2) 0.0813(2) 0.30849(15) 0.080 Uiso 1 calc R . C6 C 0.64234(14) -0.0719(2) 0.24478(13) 0.0521(4) Uani 1 d . . H61 H 0.58670(14) -0.0607(2) 0.19348(13) 0.069 Uiso 1 calc R . H62 H 0.64550(14) -0.1548(2) 0.25982(13) 0.069 Uiso 1 calc R . O10 O 0.83063(12) -0.1827(2) 0.15350(12) 0.0723(5) Uani 1 d . . O11 O 0.68291(13) -0.11892(15) 0.07354(11) 0.0668(4) Uani 1 d . . C11 C 0.75882(15) -0.1201(2) 0.14493(14) 0.0517(4) Uani 1 d . . C12 C 0.6924(3) -0.1883(3) -0.0044(2) 0.0815(8) Uani 1 d . . H122 H 0.7542(3) -0.2332(3) 0.0097(2) 0.108 Uiso 1 calc R . H121 H 0.6370(3) -0.2431(3) -0.0200(2) 0.108 Uiso 1 calc R . C13 C 0.6926(4) -0.1113(3) -0.0790(2) 0.1130(13) Uani 1 d . . H133 H 0.6362(13) -0.0592(19) -0.0870(13) 0.150 Uiso 1 calc R . H131 H 0.6885(24) -0.1570(4) -0.1326(5) 0.150 Uiso 1 calc R . H132 H 0.7534(11) -0.0661(19) -0.0671(9) 0.150 Uiso 1 calc R . O20 O 0.91432(10) 0.00974(14) 0.27761(10) 0.0578(4) Uani 1 d . . C50 C 0.5210(2) -0.0378(2) 0.3416(2) 0.0648(6) Uani 1 d . . C51 C 0.4399(2) 0.0377(3) 0.3182(2) 0.0795(7) Uani 1 d . . H511 H 0.4489(2) 0.1115(3) 0.2951(2) 0.106 Uiso 1 calc R . C52 C 0.3456(2) 0.0052(3) 0.3287(2) 0.0917(9) Uani 1 d . . H521 H 0.2920(2) 0.0569(3) 0.3120(2) 0.122 Uiso 1 calc R . C53 C 0.3310(2) -0.1024(4) 0.3633(2) 0.0908(9) Uani 1 d . . H531 H 0.2683(2) -0.1233(4) 0.3719(2) 0.121 Uiso 1 calc R . C54 C 0.4098(2) -0.1794(4) 0.3853(3) 0.1023(11) Uani 1 d . . H541 H 0.3998(2) -0.2536(4) 0.4073(3) 0.136 Uiso 1 calc R . C55 C 0.5045(2) -0.1472(3) 0.3749(2) 0.0880(9) Uani 1 d . . H551 H 0.5574(2) -0.1999(3) 0.3906(2) 0.117 Uiso 1 calc R . O2 O 1.0285(2) -0.1153(2) 0.3962(2) 0.0934(7) Uani 1 d . . O3 O 1.08716(14) 0.0724(2) 0.3305(2) 0.0923(6) Uani 1 d . . C31 C 1.0665(3) 0.1723(4) 0.3820(3) 0.1138(13) Uani 1 d . . H311 H 0.9996(3) 0.2015(4) 0.3566(3) 0.151 Uiso 1 calc R . H312 H 1.0695(3) 0.1485(4) 0.4436(3) 0.151 Uiso 1 calc R . C32 C 1.1388(4) 0.2642(4) 0.3806(3) 0.137(2) Uani 1 d . . H321 H 1.1156(13) 0.3362(8) 0.4017(23) 0.182 Uiso 1 calc R . H322 H 1.1470(21) 0.2748(23) 0.3203(5) 0.182 Uiso 1 calc R . H323 H 1.2019(8) 0.2428(15) 0.4191(20) 0.182 Uiso 1 calc R . O4 O 1.0559(2) -0.1077(2) 0.2415(2) 0.0898(6) Uani 1 d . . C41 C 1.0512(3) -0.0510(4) 0.1543(3) 0.1093(12) Uani 1 d . . H412 H 0.9848(3) -0.0188(4) 0.1313(3) 0.145 Uiso 1 calc R . H411 H 1.0993(3) 0.0127(4) 0.1611(3) 0.145 Uiso 1 calc R . C42 C 1.0737(5) -0.1380(5) 0.0921(4) 0.156(2) Uani 1 d . . H423 H 1.1373(16) -0.1737(28) 0.1173(14) 0.208 Uiso 1 calc R . H421 H 1.0761(33) -0.1006(9) 0.0362(11) 0.208 Uiso 1 calc R . H422 H 1.0225(18) -0.1973(21) 0.0816(23) 0.208 Uiso 1 calc R . O1 O 0.79723(14) 0.1157(2) 0.10026(12) 0.0764(5) Uani 1 d . . C10 C 0.6100(2) 0.1320(2) 0.1121(2) 0.0727(6) Uani 1 d . . H103 H 0.6014(4) 0.2039(9) 0.0783(11) 0.097 Uiso 1 calc R . H101 H 0.5679(2) 0.1328(18) 0.1545(2) 0.097 Uiso 1 calc R . H102 H 0.5921(5) 0.0667(9) 0.0718(10) 0.097 Uiso 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 P1 0.0467(3) 0.0637(4) 0.0795(4) 0.0028(3) -0.0013(3) 0.0009(2) S1 0.0628(3) 0.0468(3) 0.0605(3) 0.0025(2) 0.0080(2) -0.0010(2) C1 0.0440(9) 0.0475(10) 0.0501(9) -0.0012(7) 0.0075(7) -0.0007(7) C2 0.0487(10) 0.0523(11) 0.0560(10) 0.0048(8) 0.0050(8) -0.0040(8) C3 0.0634(13) 0.080(2) 0.0526(11) -0.0075(10) 0.0040(9) -0.0074(11) C4 0.0734(15) 0.094(2) 0.0523(11) -0.0046(12) 0.0153(10) -0.0063(13) C5 0.0612(12) 0.0629(13) 0.0601(11) -0.0019(10) 0.0204(9) 0.0011(10) C6 0.0458(9) 0.0537(11) 0.0564(10) 0.0018(9) 0.0107(8) -0.0026(8) O10 0.0603(9) 0.0677(10) 0.0883(11) -0.0176(9) 0.0152(8) 0.0091(8) O11 0.0719(10) 0.0675(10) 0.0559(8) -0.0160(7) 0.0040(7) 0.0039(7) C11 0.0504(10) 0.0465(10) 0.0587(11) -0.0039(8) 0.0135(8) -0.0054(8) C12 0.112(2) 0.072(2) 0.0579(13) -0.0187(12) 0.0142(13) -0.0007(15) C13 0.174(4) 0.099(3) 0.074(2) 0.006(2) 0.043(2) 0.024(2) O20 0.0454(7) 0.0580(8) 0.0660(8) 0.0058(7) 0.0038(6) -0.0038(6) C50 0.0621(13) 0.0751(15) 0.0616(12) 0.0006(11) 0.0230(10) 0.0024(10) C51 0.0691(15) 0.087(2) 0.087(2) 0.0089(14) 0.0271(13) 0.0127(13) C52 0.065(2) 0.113(3) 0.100(2) 0.008(2) 0.0252(14) 0.018(2) C53 0.069(2) 0.127(3) 0.083(2) 0.012(2) 0.0321(14) 0.002(2) C54 0.081(2) 0.116(3) 0.118(2) 0.031(2) 0.039(2) -0.005(2) C55 0.071(2) 0.093(2) 0.107(2) 0.029(2) 0.0343(15) 0.0076(14) O2 0.0740(12) 0.0918(15) 0.1007(14) 0.0238(11) -0.0094(10) 0.0052(10) O3 0.0578(10) 0.0843(13) 0.125(2) -0.0164(13) 0.0008(10) -0.0121(9) C31 0.121(3) 0.108(3) 0.114(3) -0.035(2) 0.030(2) -0.034(2) C32 0.186(5) 0.103(3) 0.127(3) -0.032(3) 0.046(3) -0.058(3) O4 0.0720(11) 0.0870(14) 0.108(2) -0.0093(11) 0.0143(11) 0.0059(9) C41 0.108(3) 0.111(3) 0.121(3) -0.002(2) 0.051(2) -0.006(2) C42 0.200(5) 0.147(5) 0.141(4) -0.022(3) 0.080(4) 0.011(4) O1 0.0772(11) 0.0815(12) 0.0746(11) 0.0186(9) 0.0256(9) -0.0062(9) C10 0.0714(14) 0.0657(15) 0.0769(15) 0.0102(12) 0.0080(11) 0.0171(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 P1 O2 1.460(2) . yes P1 O3 1.548(2) . yes P1 O4 1.547(2) . yes P1 O20 1.570(2) . yes S1 O1 1.486(2) . yes S1 C10 1.796(3) . yes S1 C1 1.896(2) . yes C1 C2 1.534(3) . yes C2 C3 1.516(3) . yes C3 C4 1.524(3) . yes C4 C5 1.522(3) . yes C5 C6 1.535(3) . yes C6 C1 1.538(3) . yes C1 C11 1.525(3) . yes C2 O20 1.454(2) . yes C5 C50 1.515(3) . yes C11 O10 1.198(3) . yes C11 O11 1.326(3) . yes O11 C12 1.458(3) . yes C12 C13 1.437(4) . yes O3 C31 1.445(4) . yes C31 C32 1.444(5) . yes O4 C41 1.466(4) . yes C41 C42 1.451(6) . yes C50 C51 1.386(4) . no C51 C52 1.388(4) . no C52 C53 1.366(5) . no C53 C54 1.372(5) . no C54 C55 1.392(4) . no C55 C50 1.381(4) . no C2 H21 0.98 . no C3 H31 0.97 . no C3 H32 0.97 . no C4 H41 0.97 . no C4 H42 0.97 . no C5 H51 0.98 . no C6 H61 0.97 . no C6 H62 0.97 . no C12 H122 0.97 . no C12 H121 0.97 . no C13 H133 0.96 . no C13 H131 0.96 . no C13 H132 0.96 . no C51 H511 0.93 . no C52 H521 0.93 . no C53 H531 0.93 . no C54 H541 0.93 . no C55 H551 0.93 . no C31 H311 0.97 . no C31 H312 0.97 . no C32 H321 0.96 . no C32 H322 0.96 . no C32 H323 0.96 . no C41 H412 0.97 . no C41 H411 0.97 . no C42 H423 0.96 . no C42 H421 0.96 . no C42 H422 0.96 . no C10 H103 0.96 . no C10 H101 0.96 . no C10 H102 0.96 . no 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 O2 P1 O3 116.85(13) . . yes O2 P1 O4 110.62(14) . . yes O3 P1 O4 104.23(13) . . yes O2 P1 O20 114.05(11) . . yes O3 P1 O20 102.44(10) . . yes O4 P1 O20 107.74(11) . . yes C2 O20 P1 121.24(13) . . yes C1 S1 O1 107.12(10) . . yes C1 S1 C10 101.26(11) . . yes O1 S1 C10 105.47(12) . . yes C11 C1 S1 107.17(13) . . yes C2 C1 S1 106.43(13) . . yes C6 C1 S1 113.97(13) . . yes C11 C1 C2 110.8(2) . . yes C11 C1 C6 109.6(2) . . yes C6 C1 C2 108.9(2) . . yes O20 C2 C1 108.1(2) . . yes O20 C2 C3 108.6(2) . . yes C1 C2 C3 113.7(2) . . yes C2 C3 C4 111.5(2) . . yes C3 C4 C5 109.8(2) . . yes C4 C5 C6 109.0(2) . . yes C5 C6 C1 114.0(2) . . yes C11 O11 C12 117.8(2) . . yes O10 C11 O11 124.7(2) . . yes O10 C11 C1 124.1(2) . . yes O11 C11 C1 111.1(2) . . yes C13 C12 O11 109.3(2) . . yes C31 O3 P1 122.9(2) . . yes O3 C31 C32 110.1(3) . . yes C41 O4 P1 120.1(2) . . yes O4 C41 C42 108.7(4) . . yes C50 C5 C4 114.6(2) . . yes C50 C5 C6 109.5(2) . . yes C5 C50 C51 119.9(2) . . no C50 C51 C52 121.2(3) . . no C51 C52 C53 120.3(3) . . no C52 C53 C54 119.5(3) . . no C53 C54 C55 120.4(3) . . no C54 C55 C50 120.9(3) . . no C55 C50 C51 117.7(2) . . no C55 C50 C5 122.3(2) . . no O20 C2 H21 108.80(10) . . no C3 C2 H21 108.80(13) . . no C1 C2 H21 108.80(10) . . no C2 C3 H31 109.32(13) . . no C4 C3 H31 109.3(2) . . no C2 C3 H32 109.32(12) . . no C4 C3 H32 109.32(13) . . no H31 C3 H32 108.0 . . no C5 C4 H41 109.71(15) . . no C3 C4 H41 109.7(2) . . no C5 C4 H42 109.71(13) . . no C3 C4 H42 109.71(14) . . no H41 C4 H42 108.2 . . no C50 C5 H51 107.86(14) . . no C4 C5 H51 107.9(2) . . no C6 C5 H51 107.86(12) . . no C5 C6 H61 108.74(11) . . no C1 C6 H61 108.74(10) . . no C5 C6 H62 108.74(12) . . no C1 C6 H62 108.74(11) . . no H61 C6 H62 107.6 . . no C13 C12 H122 109.8(2) . . no O11 C12 H122 109.81(14) . . no C13 C12 H121 109.8(2) . . no O11 C12 H121 109.81(15) . . no H122 C12 H121 108.3 . . no C12 C13 H133 109.5(2) . . no C12 C13 H131 109.5(2) . . no H133 C13 H131 109.5 . . no C12 C13 H132 109.5(2) . . no H133 C13 H132 109.5 . . no H131 C13 H132 109.5 . . no C50 C51 H511 119.4(2) . . no C52 C51 H511 119.4(2) . . no C53 C52 H521 119.9(2) . . no C51 C52 H521 119.9(2) . . no C52 C53 H531 120.3(2) . . no C54 C53 H531 120.3(2) . . no C53 C54 H541 119.8(2) . . no C55 C54 H541 119.8(2) . . no C50 C55 H551 119.6(2) . . no C54 C55 H551 119.6(2) . . no C32 C31 H311 109.6(3) . . no O3 C31 H311 109.6(2) . . no C32 C31 H312 109.6(3) . . no O3 C31 H312 109.6(2) . . no H311 C31 H312 108.2 . . no C31 C32 H321 109.5(3) . . no C31 C32 H322 109.5(2) . . no H321 C32 H322 109.5 . . no C31 C32 H323 109.5(3) . . no H321 C32 H323 109.5 . . no H322 C32 H323 109.5 . . no C42 C41 H412 110.0(3) . . no O4 C41 H412 110.0(2) . . no C42 C41 H411 110.0(3) . . no O4 C41 H411 110.0(2) . . no H412 C41 H411 108.3 . . no C41 C42 H423 109.5(3) . . no C41 C42 H421 109.5(3) . . no H423 C42 H421 109.5 . . no C41 C42 H422 109.5(3) . . no H423 C42 H422 109.5 . . no H421 C42 H422 109.5 . . no S1 C10 H103 109.47(9) . . no S1 C10 H101 109.47(10) . . no H103 C10 H101 109.5 . . no S1 C10 H102 109.47(9) . . no H103 C10 H102 109.5 . . no H101 C10 H102 109.5 . . no 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 O2 P1 O20 C2 -16.6(2) . . . . yes O3 P1 O20 C2 -143.8(2) . . . . yes O4 P1 O20 C2 106.6(2) . . . . yes P1 O20 C2 C1 -143.93(14) . . . . yes P1 O20 C2 C3 92.3(2) . . . . yes O1 S1 C1 C11 -23.8(2) . . . . yes C10 S1 C1 C11 86.4(2) . . . . yes O1 S1 C1 C2 94.77(15) . . . . yes C10 S1 C1 C2 -155.0(2) . . . . yes O1 S1 C1 C6 -145.21(15) . . . . yes C10 S1 C1 C6 -35.0(2) . . . . yes S1 C1 C2 O20 -47.7(2) . . . . yes C11 C1 C2 O20 68.4(2) . . . . yes C6 C1 C2 O20 -171.0(2) . . . . yes S1 C1 C2 C3 72.9(2) . . . . yes C11 C1 C2 C3 -170.9(2) . . . . yes O20 C2 C3 C4 175.4(2) . . . . yes C1 C2 C3 C4 55.1(3) . . . . yes C2 C3 C4 C5 -58.5(3) . . . . yes C3 C4 C5 C6 58.8(3) . . . . yes C4 C5 C6 C1 -57.8(3) . . . . yes C5 C6 C1 C2 52.4(2) . . . . yes C6 C1 C2 C3 -50.4(2) . . . . yes S1 C1 C6 C5 -66.2(2) . . . . yes C11 C1 C6 C5 173.7(2) . . . . yes C12 O11 C11 C1 176.1(2) . . . . yes C12 O11 C11 O10 -7.5(3) . . . . yes S1 C1 C11 O10 117.5(2) . . . . yes C2 C1 C11 O10 1.8(3) . . . . yes C6 C1 C11 O10 -118.4(2) . . . . yes S1 C1 C11 O11 -66.0(2) . . . . yes C2 C1 C11 O11 178.2(2) . . . . yes C6 C1 C11 O11 58.1(2) . . . . yes C11 O11 C12 C13 -115.6(3) . . . . yes O20 P1 O3 C31 54.8(3) . . . . yes O2 P1 O3 C31 -70.6(3) . . . . yes O4 P1 O3 C31 167.0(3) . . . . yes P1 O3 C31 C32 -178.9(3) . . . . yes O20 P1 O4 C41 51.9(3) . . . . yes O2 P1 O4 C41 177.2(2) . . . . yes O3 P1 O4 C41 -56.4(3) . . . . yes P1 O4 C41 C42 -172.2(3) . . . . yes C50 C5 C4 C3 -178.1(2) . . . . yes C50 C5 C6 C1 176.2(2) . . . . yes C4 C5 C50 C51 130.9(3) . . . . yes C6 C5 C50 C51 -106.4(3) . . . . yes C4 C5 C50 C55 -53.1(4) . . . . no C6 C5 C50 C55 69.6(3) . . . . no C5 C50 C51 C52 176.8(3) . . . . no C55 C50 C51 C52 0.6(5) . . . . no C50 C51 C52 C53 0.6(5) . . . . no C51 C52 C53 C54 -1.9(5) . . . . no C52 C53 C54 C55 1.9(6) . . . . no C53 C54 C55 C50 -0.6(6) . . . . no C54 C55 C50 C51 -0.6(5) . . . . no C54 C55 C50 C5 -176.7(3) . . . . no loop_ _publ_manuscript_incl_extra_item '_geom_bond_atom_site_label_D' '_geom_bond_atom_site_label_H' '_geom_contact_atom_site_label_A' '_geom_bond_distance_DH' '_geom_contact_distance_HA' '_geom_contact_distance_DA' '_geom_angle_DHA' '_geom_contact_site_symmetry_A' '_geom_extra_tableA_col_1' '_geom_extra_tableA_col_2' '_geom_extra_tableA_col_3' '_geom_extra_tableA_col_4' '_geom_extra_table_head_A' '_geom_extra_tableB_col_1' '_geom_extra_tableB_col_2' '_geom_extra_tableB_col_3' '_geom_extra_tableB_col_4' '_geom_extra_tableB_col_5' '_geom_extra_table_head_B' '_geom_extra_tableC_col_1' '_geom_extra_tableC_col_2' '_geom_extra_tableC_col_3' '_geom_extra_tableC_col_4' '_geom_extra_tableC_col_5' '_geom_extra_table_head_C' loop_ _geom_bond_atom_site_label_D _geom_bond_atom_site_label_H _geom_contact_atom_site_label_A _geom_bond_distance_DH _geom_contact_distance_HA _geom_contact_distance_DA _geom_angle_DHA _geom_contact_site_symmetry_A C2 H21 O10 0.980 2.571 2.778(3) 91.7 . C2 H21 O2 0.980 2.585 2.945(4) 101.8 . C6 H61 O11 0.970 2.572 2.842(2) 96.0 . C6 H61 C10 0.970 2.575 3.045(3) 109.9 . C12 H122 O10 0.970 2.281 2.709(3) 105.6 . C12 H121 O2 0.969 2.363 3.286(4) 159.0 4_555 C31 H311 O20 0.970 2.636 2.969(4) 100.4 . C41 H412 O20 0.970 2.644 3.020(5) 103.4 . C41 H411 O3 0.969 2.712 2.973(5) 95.9 . C10 H102 O11 0.960 2.448 3.124(3) 127.2 . _geom_extra_table_head_A ; Asymmetry parameters (Duax & Norton, 1975) of six-membered ring C1,C2,C3,C4,C5,C6. ; loop_ _geom_extra_tableA_col_1 _geom_extra_tableA_col_2 _geom_extra_tableA_col_3 _geom_extra_tableA_col_4 \DC~s~^(C1)^=\DC~s~^(C4)^ 1.9(4) \DC~2~^(C1\\-C2)^=\DC~2~^(C4\\-C5)^ 2.0(4) \DC~s~^(C2)^=\DC~s~^(C5)^ 4.5(5) \DC~2~^(C2\\-C3)^=\DC~2~^(C5\\-C6)^ 7.3(5) \DC~s~^(C3)^=\DC~s~^(C6)^ 6.1(5) \DC~2~^(C3\\-C4)^=\DC~2~^(C6\\-C1)^ 5.9(5) loop_ _geom_extra_tableB_col_1 _geom_extra_tableB_col_2 _geom_extra_tableB_col_3 _geom_extra_tableB_col_4 _geom_extra_tableB_col_5 'Plane1' C1,C3,C4,C6 ? 'Plane1^\\wedge^Plane2' 45.78(17) 'Plane2' C1,C2,C3 ? 'Plane1^\\wedge^Plane3' 53.44(23) 'Plane3' C4,C5,C6 ? 'Plane2^\\wedge^Plane3' 7.71(28) 'Plane4' C50,C51,C52,C53,C54,C55 ? 'Plane1^\\wedge^Plane4' 80.48(10) ? ? ? 'Plane2^\\wedge^Plane4' 57.43(17) ? ? ? 'Plane3^\\wedge^Plane4' 50.19(23) ? A B C D 'Plane1' 0.0669(10) 0.8501(9) -0.5224(14) -2.0558(94) 'Plane2' 0.2129(14) -0.9573(7) -0.1956(28) 1.7662(128) 'Plane3' 0.2352(21) -0.9171(18) -0.3219(41) 0.2090(183) 'Plane4' -0.0076(13) -0.3746(14) -0.9272(6) -4.5843(75) _geom_extra_table_head_C ; Distances (\%A) of non-hydrogen atoms from weighted least-squares planes 1a and 1b (^*^ indicates atom used to define plane) ; loop_ _geom_extra_tableC_col_1 _geom_extra_tableC_col_2 _geom_extra_tableC_col_3 _geom_extra_tableC_col_4 _geom_extra_tableC_col_5 ? 'Plane1' 'Plane2' 'Plane3' 'Plane4' P1 '0.068(1)' '0.497(1)' '1.728(1)' '0.283(1)' S1 '2.506(1)' '-1.520(1)' '-0.017(1)' '1.651(1)' C1 '0.640(2)' '0.000(2)^*^' '1.341(2)' '1.672(1)' C2 '0.007(2)^*^' '0.000(2)^*^' '1.203(2)' '0.535(1)' C3 '-0.017(3)^*^' '-1.070(3)' '0.000(3)^*^' '-0.848(3)' C4 '-0.707(3)' '-0.974(3)' '0.000(3)^*^' '-0.984(3)' C5 '0.010(2)^*^' '-1.112(2)' '0.000(2)^*^' '0.062(2)' C6 '-0.007(2)^*^' '0.000(2)^*^' '1.242(2)' '1.458(1)' O10 '-0.176(2)' '2.088(2)' '3.516(2)' '3.166(1)' O11 '0.945(2)' '1.254(2)' '2.822(2)' '4.010(1)' C11 '0.431(2)' '1.229(2)' '2.681(2)' '3.025(1)' C12 '0.904(3)' '2.322(3)' '4.013(3)' '5.376(3)' C13 '2.246(3)' '1.754(3)' '3.626(3)' '6.073(3)' O20 '0.770(1)' '-0.215(1)' '1.084(1)' '0.631(1)' C50 '-0.562(2)' '-1.078(2)' '-0.046(2)' '-0.006(2)^*^' C51 '0.281(3)' '-2.051(3)' '-0.964(3)' '0.002(3)^*^' C52 '-0.204(4)' '-2.011(4)' '-0.988(4)' '0.006(3)^*^' C53 '-1.535(4)' '-1.007(4)' '-0.105(4)' '-0.010(3)^*^' C54 '-2.383(4)' '-0.019(4)' '0.829(4)' '0.008(4)^*^' C55 '-1.901(3)' '-0.055(3)' '0.856(3)' '0.004(3)^*^' O2 '-1.282(2)' '1.048(2)' '2.093(2)' '-0.479(2)' O3 '1.112(2)' '-0.586(2)' '0.691(2)' '-0.382(2)' C31 '1.648(4)' '-1.922(4)' '-0.706(4)' '-1.514(4)' C32 '2.613(4)' '-2.707(4)' '-1.424(4)' '-1.895(4)' O4 '0.053(2)' '1.609(2)' '2.967(2)' '1.613(2)' C41 '1.294(4)' '1.295(4)' '2.848(4)' '2.571(4)' C42 '0.970(5)' '2.534(5)' '4.177(5)' '3.795(5)' O1 '3.105(2)' '-1.066(2)' '0.592(2)' '2.629(1)' C10 '2.996(2)' '-1.832(2)' '-0.247(2)' '2.417(2)' #+------------------------------------------------------------