Supplementary Material for Organic & Biomolecular Chemistry This journal is © The Royal Society of Chemistry 2005 data_global _journal_name_full Org.Biomol.Chem. _journal_coden_Cambridge 0177 _publ_contact_author_name 'Prof James Utley' _publ_contact_author_address ; Chemistry Queen Mary University of London Mile End Road London E1 4NS UNITED KINGDOM ; _publ_contact_author_email J.UTLEY@QMUL.AC.UK _publ_section_title ; The reactivity, as electrogenerated bases, of chiral and achiral phenazine radical-anions, including application in asymmetric deprotonation ; loop_ _publ_author_name 'James Utley' 'A. Mateo Alonso' 'Roberto Horcajada' 'Majid Motevalli' 'Peter B. Wyatt' data_ama-192-5 _database_code_depnum_ccdc_archive 'CCDC 266539' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C13 H15 Cl O5 S' _chemical_formula_weight 318.76 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' S S 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Orthorhombic _symmetry_space_group_name_H-M P212121 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 6.8530(2) _cell_length_b 9.6726(3) _cell_length_c 21.2802(7) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 1410.59(8) _cell_formula_units_Z 4 _cell_measurement_temperature 120(2) _cell_measurement_reflns_used 23832 _cell_measurement_theta_min 2.91 _cell_measurement_theta_max 27.48 _exptl_crystal_description block _exptl_crystal_colour colourless _exptl_crystal_size_max 0.40 _exptl_crystal_size_mid 0.35 _exptl_crystal_size_min 0.10 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.501 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 664 _exptl_absorpt_coefficient_mu 0.434 _exptl_absorpt_correction_type Multi-scan _exptl_absorpt_correction_T_min 0.87611 _exptl_absorpt_correction_T_max 0.99988 _exptl_absorpt_process_details 'SADABS V2.10 (Sheldrick, G.M.,2003)' _diffrn_ambient_temperature 120(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'Bruker-Nonius FR591 rotating anode' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Bruker-Nonius 95mm CCD camera on \k-goniostat' _diffrn_measurement_method '\f & \w scans' _diffrn_detector_area_resol_mean 9.091 _diffrn_standards_decay_% 0 _diffrn_reflns_number 10821 _diffrn_reflns_av_R_equivalents 0.0472 _diffrn_reflns_av_sigmaI/netI 0.0361 _diffrn_reflns_limit_h_min -6 _diffrn_reflns_limit_h_max 8 _diffrn_reflns_limit_k_min -12 _diffrn_reflns_limit_k_max 12 _diffrn_reflns_limit_l_min -27 _diffrn_reflns_limit_l_max 26 _diffrn_reflns_theta_min 3.54 _diffrn_reflns_theta_max 27.47 _reflns_number_total 3199 _reflns_number_gt 2998 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'COLLECT (Hooft, R.W.W., 1998)' _computing_cell_refinement 'DENZO (Otwinowski & Minor, 1997) & COLLECT (Hooft, R.W.W., 1998)' #Although determined using DirAx, the cell is refined in the HKL #package during data reduction _computing_data_reduction 'DENZO (Otwinowski & Minor, 1997) & COLLECT (Hooft, R.W.W., 1998)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1997b)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997b)' _computing_molecular_graphics 'Ortep-3 for Windows (Farrugia, 1997) &PLUTON (Spek,A.L.,1990)' _computing_publication_material 'WinGX publication routines (Farrugia, 1999)' _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0321P)^2^+0.3143P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment mixed _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881' _refine_ls_abs_structure_Flack -0.05(5) _refine_ls_number_reflns 3199 _refine_ls_number_parameters 182 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0309 _refine_ls_R_factor_gt 0.0276 _refine_ls_wR_factor_ref 0.0683 _refine_ls_wR_factor_gt 0.0666 _refine_ls_goodness_of_fit_ref 1.051 _refine_ls_restrained_S_all 1.051 _refine_ls_shift/su_max 0.001 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group C1 C 0.3695(3) 0.42287(19) 0.86915(8) 0.0196(4) Uani 1 1 d . . . H1A H 0.3902 0.4644 0.9111 0.024 Uiso 1 1 calc R . . H1B H 0.3099 0.4932 0.8413 0.024 Uiso 1 1 calc R . . C2 C 0.2391(2) 0.29605(19) 0.87390(7) 0.0179(3) Uani 1 1 d . . . H2 H 0.0988 0.3243 0.8728 0.021 Uiso 1 1 calc R . . C3 C 0.2863(2) 0.20390(17) 0.81719(7) 0.0154(3) Uani 1 1 d . . . H3 H 0.2339 0.1084 0.8235 0.018 Uiso 1 1 calc R . . C4 C 0.5054(2) 0.20071(18) 0.80825(8) 0.0167(3) Uani 1 1 d . . . H4A H 0.5382 0.1891 0.7633 0.020 Uiso 1 1 calc R . . H4B H 0.5634 0.1231 0.8321 0.020 Uiso 1 1 calc R . . C5 C 0.0242(2) 0.21623(17) 0.74533(7) 0.0137(3) Uani 1 1 d . . . C6 C -0.0586(2) 0.29513(17) 0.68957(7) 0.0133(3) Uani 1 1 d . . . H6 H -0.0804 0.3936 0.7021 0.016 Uiso 1 1 calc R . . C7 C 0.0716(2) 0.29138(18) 0.63207(7) 0.0148(3) Uani 1 1 d . . . C8 C 0.1277(3) 0.41260(19) 0.60224(8) 0.0201(4) Uani 1 1 d . . . H8 H 0.0938 0.4998 0.6197 0.024 Uiso 1 1 calc R . . C9 C 0.2340(3) 0.4056(2) 0.54662(8) 0.0258(4) Uani 1 1 d . . . H9 H 0.2725 0.4884 0.5261 0.031 Uiso 1 1 calc R . . C10 C 0.2843(3) 0.2787(2) 0.52100(8) 0.0271(4) Uani 1 1 d . . . H10 H 0.3557 0.2747 0.4828 0.032 Uiso 1 1 calc R . . C11 C 0.2303(2) 0.1579(2) 0.55113(8) 0.0234(4) Uani 1 1 d . . . H11 H 0.2660 0.0709 0.5339 0.028 Uiso 1 1 calc R . . C12 C 0.1240(2) 0.16389(18) 0.60642(8) 0.0181(4) Uani 1 1 d . . . H12 H 0.0866 0.0808 0.6270 0.022 Uiso 1 1 calc R . . C13 C -0.3713(2) 0.3196(2) 0.64307(8) 0.0207(4) Uani 1 1 d . . . H13A H -0.4082 0.3985 0.6694 0.031 Uiso 1 1 calc R . . H13B H -0.4886 0.2675 0.6315 0.031 Uiso 1 1 calc R . . H13C H -0.3065 0.3532 0.6049 0.031 Uiso 1 1 calc R . . O1 O -0.05675(17) 0.12341(13) 0.77186(6) 0.0227(3) Uani 1 1 d . . . O2 O 0.6535(2) 0.45238(13) 0.78606(6) 0.0240(3) Uani 1 1 d . . . O3 O 0.73710(18) 0.33849(13) 0.88584(6) 0.0247(3) Uani 1 1 d . . . O4 O 0.19991(17) 0.26749(12) 0.76221(5) 0.0164(2) Uani 1 1 d . . . O7 O -0.24185(16) 0.23224(11) 0.67694(5) 0.0162(3) Uani 1 1 d . . . S1 S 0.59641(6) 0.36303(4) 0.836968(19) 0.01603(10) Uani 1 1 d . . . Cl1 Cl 0.28888(7) 0.20061(5) 0.94432(2) 0.02972(12) Uani 1 1 d . . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 C1 0.0190(9) 0.0202(8) 0.0197(8) -0.0031(7) 0.0010(7) 0.0034(7) C2 0.0146(8) 0.0246(8) 0.0146(7) 0.0039(7) -0.0008(6) 0.0008(7) C3 0.0129(8) 0.0174(7) 0.0157(8) 0.0046(6) -0.0039(6) -0.0008(7) C4 0.0137(8) 0.0150(8) 0.0214(8) -0.0018(7) -0.0016(6) 0.0002(7) C5 0.0107(7) 0.0153(7) 0.0150(7) -0.0030(6) 0.0001(6) 0.0014(6) C6 0.0101(7) 0.0129(7) 0.0170(7) -0.0015(6) -0.0014(6) -0.0005(6) C7 0.0100(7) 0.0208(8) 0.0137(7) 0.0001(7) -0.0023(6) 0.0011(7) C8 0.0173(8) 0.0242(8) 0.0188(8) 0.0023(7) -0.0026(7) -0.0019(7) C9 0.0177(9) 0.0401(11) 0.0197(9) 0.0077(8) -0.0015(7) -0.0079(8) C10 0.0137(8) 0.0523(12) 0.0152(8) -0.0019(8) -0.0007(7) -0.0004(9) C11 0.0139(8) 0.0366(10) 0.0198(8) -0.0090(8) -0.0034(7) 0.0058(8) C12 0.0131(8) 0.0237(9) 0.0174(8) -0.0014(7) -0.0029(6) 0.0029(7) C13 0.0140(8) 0.0269(9) 0.0212(8) -0.0005(7) -0.0052(6) 0.0016(7) O1 0.0154(6) 0.0236(6) 0.0292(7) 0.0109(6) -0.0030(5) -0.0041(5) O2 0.0288(7) 0.0221(6) 0.0212(7) 0.0001(5) 0.0057(5) -0.0071(5) O3 0.0173(6) 0.0304(7) 0.0265(7) -0.0017(6) -0.0067(5) -0.0016(5) O4 0.0149(6) 0.0195(6) 0.0148(6) 0.0041(5) -0.0053(5) -0.0033(5) O7 0.0105(5) 0.0173(5) 0.0207(6) -0.0006(5) -0.0031(4) -0.0007(4) S1 0.01326(18) 0.01708(18) 0.01776(19) -0.00106(16) -0.00004(16) -0.00249(16) Cl1 0.0327(3) 0.0389(3) 0.0176(2) 0.0091(2) -0.00231(18) -0.0058(2) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag C1 C2 1.521(2) . ? C1 S1 1.7948(17) . ? C1 H1A 0.9900 . ? C1 H1B 0.9900 . ? C2 C3 1.535(2) . ? C2 Cl1 1.7928(17) . ? C2 H2 1.0000 . ? C3 O4 1.4484(19) . ? C3 C4 1.514(2) . ? C3 H3 1.0000 . ? C4 S1 1.7966(18) . ? C4 H4A 0.9900 . ? C4 H4B 0.9900 . ? C5 O1 1.197(2) . ? C5 O4 1.3508(19) . ? C5 C6 1.521(2) . ? C6 O7 1.4212(18) . ? C6 C7 1.515(2) . ? C6 H6 1.0000 . ? C7 C8 1.388(2) . ? C7 C12 1.396(2) . ? C8 C9 1.391(2) . ? C8 H8 0.9500 . ? C9 C10 1.387(3) . ? C9 H9 0.9500 . ? C10 C11 1.383(3) . ? C10 H10 0.9500 . ? C11 C12 1.385(2) . ? C11 H11 0.9500 . ? C12 H12 0.9500 . ? C13 O7 1.422(2) . ? C13 H13A 0.9800 . ? C13 H13B 0.9800 . ? C13 H13C 0.9800 . ? O2 S1 1.4401(13) . ? O3 S1 1.4378(13) . ? 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 C2 C1 S1 105.92(12) . . ? C2 C1 H1A 110.6 . . ? S1 C1 H1A 110.6 . . ? C2 C1 H1B 110.6 . . ? S1 C1 H1B 110.6 . . ? H1A C1 H1B 108.7 . . ? C1 C2 C3 106.99(13) . . ? C1 C2 Cl1 111.04(12) . . ? C3 C2 Cl1 108.55(12) . . ? C1 C2 H2 110.1 . . ? C3 C2 H2 110.1 . . ? Cl1 C2 H2 110.1 . . ? O4 C3 C4 108.23(13) . . ? O4 C3 C2 107.59(13) . . ? C4 C3 C2 108.65(14) . . ? O4 C3 H3 110.8 . . ? C4 C3 H3 110.8 . . ? C2 C3 H3 110.8 . . ? C3 C4 S1 106.48(12) . . ? C3 C4 H4A 110.4 . . ? S1 C4 H4A 110.4 . . ? C3 C4 H4B 110.4 . . ? S1 C4 H4B 110.4 . . ? H4A C4 H4B 108.6 . . ? O1 C5 O4 124.26(15) . . ? O1 C5 C6 124.86(15) . . ? O4 C5 C6 110.85(13) . . ? O7 C6 C7 110.96(12) . . ? O7 C6 C5 105.22(13) . . ? C7 C6 C5 113.48(13) . . ? O7 C6 H6 109.0 . . ? C7 C6 H6 109.0 . . ? C5 C6 H6 109.0 . . ? C8 C7 C12 119.77(15) . . ? C8 C7 C6 120.83(15) . . ? C12 C7 C6 119.25(15) . . ? C7 C8 C9 119.55(17) . . ? C7 C8 H8 120.2 . . ? C9 C8 H8 120.2 . . ? C10 C9 C8 120.48(17) . . ? C10 C9 H9 119.8 . . ? C8 C9 H9 119.8 . . ? C11 C10 C9 119.95(16) . . ? C11 C10 H10 120.0 . . ? C9 C10 H10 120.0 . . ? C10 C11 C12 119.95(17) . . ? C10 C11 H11 120.0 . . ? C12 C11 H11 120.0 . . ? C11 C12 C7 120.30(16) . . ? C11 C12 H12 119.9 . . ? C7 C12 H12 119.9 . . ? O7 C13 H13A 109.5 . . ? O7 C13 H13B 109.5 . . ? H13A C13 H13B 109.5 . . ? O7 C13 H13C 109.5 . . ? H13A C13 H13C 109.5 . . ? H13B C13 H13C 109.5 . . ? C5 O4 C3 115.06(12) . . ? C6 O7 C13 113.13(12) . . ? O3 S1 O2 117.45(8) . . ? O3 S1 C1 110.99(8) . . ? O2 S1 C1 109.21(8) . . ? O3 S1 C4 109.54(8) . . ? O2 S1 C4 111.28(8) . . ? C1 S1 C4 96.36(8) . . ? _diffrn_measured_fraction_theta_max 0.993 _diffrn_reflns_theta_full 27.47 _diffrn_measured_fraction_theta_full 0.993 _refine_diff_density_max 0.185 _refine_diff_density_min -0.325 _refine_diff_density_rms 0.047 data_ama-157 _database_code_depnum_ccdc_archive 'CCDC 269382' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C14 H16 O4 S' _chemical_formula_weight 280.33 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' S S 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Monoclinic _symmetry_space_group_name_H-M P21/c loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y-1/2, z-1/2' _cell_length_a 21.102(8) _cell_length_b 10.963(6) _cell_length_c 5.929(2) _cell_angle_alpha 90.00 _cell_angle_beta 92.57(5) _cell_angle_gamma 90.00 _cell_volume 1370.2(10) _cell_formula_units_Z 4 _cell_measurement_temperature 160(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description plate _exptl_crystal_colour colourless _exptl_crystal_size_max 0.40 _exptl_crystal_size_mid 0.20 _exptl_crystal_size_min 0.05 _exptl_crystal_density_meas 'not measured' _exptl_crystal_density_diffrn 1.359 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 592 _exptl_absorpt_coefficient_mu 0.243 _exptl_absorpt_correction_type psi-scan _exptl_absorpt_correction_T_min 0.9090 _exptl_absorpt_correction_T_max 0.9879 _exptl_absorpt_process_details ; North A.C.T., Phillips D.C. & Mathews F.S. (1968) Acta. Cryst. A24, 351 Number of psi-scan sets used was 3 Theta correction was applied. Averaged transmission function was used. No Fourier smoothing was applied. ; _diffrn_ambient_temperature 160(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Enraf Nonius CAD4' _diffrn_measurement_method 'non-profiled omega/2theta scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number 2 _diffrn_standards_interval_count 100 _diffrn_standards_interval_time 60 _diffrn_standards_decay_% 2 _diffrn_reflns_number 2730 _diffrn_reflns_av_R_equivalents 0.0192 _diffrn_reflns_av_sigmaI/netI 0.0933 _diffrn_reflns_limit_h_min -25 _diffrn_reflns_limit_h_max 25 _diffrn_reflns_limit_k_min 0 _diffrn_reflns_limit_k_max 13 _diffrn_reflns_limit_l_min 0 _diffrn_reflns_limit_l_max 7 _diffrn_reflns_theta_min 2.09 _diffrn_reflns_theta_max 24.99 _reflns_number_total 2394 _reflns_number_gt 1400 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'CAD4 /PC (Enraf Nonius, 1994)' _computing_cell_refinement 'CAD4 /PC (Enraf Nonius, 1994)' _computing_data_reduction 'XCAD4 (Harms & Wocadlo, 1995)' _computing_structure_solution 'SHELXL-97 (Sheldrick, 1997)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Ortep-3 for Windows (Farrugia, 1997)' _computing_publication_material 'WinGX publication routines (Farrugia, 1999)' _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0794P)^2^+0.2457P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment mixed _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 2394 _refine_ls_number_parameters 175 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.1293 _refine_ls_R_factor_gt 0.0521 _refine_ls_wR_factor_ref 0.1498 _refine_ls_wR_factor_gt 0.1250 _refine_ls_goodness_of_fit_ref 1.008 _refine_ls_restrained_S_all 1.008 _refine_ls_shift/su_max 0.017 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group S1 S 0.43681(4) 0.93814(9) 0.26749(17) 0.0271(3) Uani 1 1 d . . . O1 O 0.50423(13) 0.9202(3) 0.2624(5) 0.0391(7) Uani 1 1 d . . . O2 O 0.40441(13) 0.8794(3) 0.4452(5) 0.0390(8) Uani 1 1 d . . . O3 O 0.29849(11) 0.9907(2) -0.1043(4) 0.0298(7) Uani 1 1 d . . . O4 O 0.28531(13) 1.1333(3) -0.3739(6) 0.0453(8) Uani 1 1 d . . . C1 C 0.41654(18) 1.0921(3) 0.2621(7) 0.0272(9) Uani 1 1 d . . . H1 H 0.4310 1.1499 0.3722 0.033 Uiso 1 1 calc R . . C2 C 0.37854(18) 1.1185(4) 0.0853(7) 0.0300(9) Uani 1 1 d . . . H2 H 0.3599 1.1970 0.0670 0.036 Uiso 1 1 calc R . . C3 C 0.36619(17) 1.0201(3) -0.0833(7) 0.0277(9) Uani 1 1 d . . . H3 H 0.3818 1.0452 -0.2332 0.033 Uiso 1 1 calc R . . C4 C 0.40027(18) 0.9041(3) -0.0014(7) 0.0315(10) Uani 1 1 d . . . H4A H 0.4326 0.8798 -0.1086 0.038 Uiso 1 1 calc R . . H4B H 0.3696 0.8364 0.0112 0.038 Uiso 1 1 calc R . . C5 C 0.26414(17) 1.0531(4) -0.2632(7) 0.0283(9) Uani 1 1 d . . . C6 C 0.19812(17) 1.0033(4) -0.2859(6) 0.0272(9) Uani 1 1 d . . . C7 C 0.15230(18) 1.0435(4) -0.1432(7) 0.0317(10) Uani 1 1 d . . . C8 C 0.09170(18) 0.9937(4) -0.1700(7) 0.0394(11) Uani 1 1 d . . . H8 H 0.0599 1.0202 -0.0728 0.047 Uiso 1 1 calc R . . C9 C 0.07627(19) 0.9078(4) -0.3316(7) 0.0388(11) Uani 1 1 d . . . C10 C 0.12325(19) 0.8691(4) -0.4711(7) 0.0380(11) Uani 1 1 d . . . H10 H 0.1131 0.8095 -0.5834 0.046 Uiso 1 1 calc R . . C11 C 0.18487(19) 0.9148(4) -0.4517(7) 0.0333(10) Uani 1 1 d . . . C12 C 0.1667(2) 1.1388(4) 0.0372(8) 0.0462(12) Uani 1 1 d . . . H12A H 0.1774 1.0982 0.1812 0.069 Uiso 1 1 calc R . . H12B H 0.1294 1.1908 0.0533 0.069 Uiso 1 1 calc R . . H12C H 0.2026 1.1888 -0.0065 0.069 Uiso 1 1 calc R . . C13 C 0.0105(2) 0.8541(5) -0.3593(9) 0.0602(15) Uani 1 1 d . . . H13A H -0.0093 0.8806 -0.5037 0.090 Uiso 1 1 calc R . . H13B H -0.0152 0.8819 -0.2356 0.090 Uiso 1 1 calc R . . H13C H 0.0133 0.7648 -0.3566 0.090 Uiso 1 1 calc R . . C14 C 0.2349(2) 0.8687(4) -0.6007(8) 0.0452(12) Uani 1 1 d . . . H14A H 0.2227 0.7880 -0.6593 0.068 Uiso 1 1 calc R . . H14B H 0.2753 0.8625 -0.5137 0.068 Uiso 1 1 calc R . . H14C H 0.2394 0.9252 -0.7270 0.068 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 S1 0.0273(5) 0.0223(5) 0.0315(6) 0.0009(5) -0.0004(4) 0.0028(4) O1 0.0263(14) 0.0443(18) 0.0462(17) -0.0057(15) -0.0023(12) 0.0089(13) O2 0.0468(18) 0.0324(16) 0.0381(17) 0.0054(14) 0.0064(14) -0.0028(13) O3 0.0197(13) 0.0352(16) 0.0341(15) 0.0083(13) -0.0038(11) -0.0043(12) O4 0.0336(16) 0.0382(18) 0.063(2) 0.0254(17) -0.0077(15) -0.0073(13) C1 0.031(2) 0.022(2) 0.028(2) -0.0041(17) 0.0056(18) -0.0037(16) C2 0.027(2) 0.023(2) 0.040(3) 0.0027(19) 0.0016(19) 0.0032(17) C3 0.021(2) 0.029(2) 0.034(2) 0.0028(18) 0.0000(17) -0.0031(16) C4 0.031(2) 0.024(2) 0.039(2) -0.0050(18) -0.0044(18) 0.0011(16) C5 0.024(2) 0.029(2) 0.032(2) 0.000(2) 0.0008(17) 0.0011(18) C6 0.024(2) 0.027(2) 0.030(2) 0.0066(19) -0.0039(16) -0.0021(17) C7 0.029(2) 0.031(2) 0.035(2) 0.0000(19) -0.0021(18) 0.0013(17) C8 0.024(2) 0.048(3) 0.047(3) -0.001(2) 0.008(2) -0.002(2) C9 0.024(2) 0.049(3) 0.043(3) 0.003(2) -0.0027(19) -0.0099(19) C10 0.037(2) 0.037(2) 0.039(3) -0.001(2) -0.003(2) -0.0092(19) C11 0.037(2) 0.033(2) 0.030(2) 0.0051(19) 0.0017(19) 0.0000(18) C12 0.040(3) 0.050(3) 0.049(3) -0.010(2) 0.002(2) -0.004(2) C13 0.035(3) 0.073(4) 0.072(4) -0.010(3) 0.004(2) -0.017(3) C14 0.038(3) 0.049(3) 0.050(3) -0.006(2) 0.010(2) -0.006(2) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag S1 O2 1.434(3) . ? S1 O1 1.438(3) . ? S1 C1 1.742(4) . ? S1 C4 1.779(4) . ? O3 C5 1.349(4) . ? O3 C3 1.464(4) . ? O4 C5 1.196(5) . ? C1 C2 1.323(5) . ? C1 H1 0.9500 . ? C2 C3 1.486(5) . ? C2 H2 0.9500 . ? C3 C4 1.529(5) . ? C3 H3 1.0000 . ? C4 H4A 0.9900 . ? C4 H4B 0.9900 . ? C5 C6 1.497(5) . ? C6 C7 1.385(5) . ? C6 C11 1.400(6) . ? C7 C8 1.393(5) . ? C7 C12 1.516(6) . ? C8 C9 1.373(6) . ? C8 H8 0.9500 . ? C9 C10 1.386(6) . ? C9 C13 1.510(6) . ? C10 C11 1.394(6) . ? C10 H10 0.9500 . ? C11 C14 1.495(6) . ? C12 H12A 0.9800 . ? C12 H12B 0.9800 . ? C12 H12C 0.9800 . ? C13 H13A 0.9800 . ? C13 H13B 0.9800 . ? C13 H13C 0.9800 . ? C14 H14A 0.9800 . ? C14 H14B 0.9800 . ? C14 H14C 0.9800 . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag O2 S1 O1 117.28(18) . . ? O2 S1 C1 108.92(18) . . ? O1 S1 C1 112.00(18) . . ? O2 S1 C4 111.25(18) . . ? O1 S1 C4 110.01(19) . . ? C1 S1 C4 95.20(19) . . ? C5 O3 C3 116.1(3) . . ? C2 C1 S1 111.5(3) . . ? C2 C1 H1 124.3 . . ? S1 C1 H1 124.3 . . ? C1 C2 C3 117.1(4) . . ? C1 C2 H2 121.4 . . ? C3 C2 H2 121.4 . . ? O3 C3 C2 111.0(3) . . ? O3 C3 C4 106.7(3) . . ? C2 C3 C4 108.9(3) . . ? O3 C3 H3 110.1 . . ? C2 C3 H3 110.1 . . ? C4 C3 H3 110.1 . . ? C3 C4 S1 106.8(3) . . ? C3 C4 H4A 110.4 . . ? S1 C4 H4A 110.4 . . ? C3 C4 H4B 110.4 . . ? S1 C4 H4B 110.4 . . ? H4A C4 H4B 108.6 . . ? O4 C5 O3 123.6(3) . . ? O4 C5 C6 126.0(4) . . ? O3 C5 C6 110.3(3) . . ? C7 C6 C11 121.8(4) . . ? C7 C6 C5 120.1(4) . . ? C11 C6 C5 118.1(3) . . ? C6 C7 C8 117.9(4) . . ? C6 C7 C12 121.8(4) . . ? C8 C7 C12 120.3(4) . . ? C9 C8 C7 122.4(4) . . ? C9 C8 H8 118.8 . . ? C7 C8 H8 118.8 . . ? C8 C9 C10 118.2(4) . . ? C8 C9 C13 122.1(4) . . ? C10 C9 C13 119.6(4) . . ? C9 C10 C11 122.0(4) . . ? C9 C10 H10 119.0 . . ? C11 C10 H10 119.0 . . ? C10 C11 C6 117.6(4) . . ? C10 C11 C14 120.7(4) . . ? C6 C11 C14 121.7(4) . . ? C7 C12 H12A 109.5 . . ? C7 C12 H12B 109.5 . . ? H12A C12 H12B 109.5 . . ? C7 C12 H12C 109.5 . . ? H12A C12 H12C 109.5 . . ? H12B C12 H12C 109.5 . . ? C9 C13 H13A 109.5 . . ? C9 C13 H13B 109.5 . . ? H13A C13 H13B 109.5 . . ? C9 C13 H13C 109.5 . . ? H13A C13 H13C 109.5 . . ? H13B C13 H13C 109.5 . . ? C11 C14 H14A 109.5 . . ? C11 C14 H14B 109.5 . . ? H14A C14 H14B 109.5 . . ? C11 C14 H14C 109.5 . . ? H14A C14 H14C 109.5 . . ? H14B C14 H14C 109.5 . . ? _diffrn_measured_fraction_theta_max 0.997 _diffrn_reflns_theta_full 24.99 _diffrn_measured_fraction_theta_full 0.997 _refine_diff_density_max 0.398 _refine_diff_density_min -0.429 _refine_diff_density_rms 0.070