# Supplementary Material (ESI) for Perkin Transactions # This journal is © The Royal Society of Chemistry 2000 # CCDC Number: 188/267 data_2,2'-diphenyl-2,2'-bis(1,3-dithianyl) #1 _audit_creation_method SHELXL _chemical_name_systematic ; 2,2'-diphenyl-2,2'-bis(1,3-dithianyl) ; _chemical_name_common ? _chemical_formula_moiety ? _chemical_formula_structural ? _chemical_formula_analytical ? _chemical_formula_sum 'C20 H22 S4' _chemical_formula_weight 390.62 _chemical_melting_point 205.0oC _chemical_compound_source 'see text' 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' '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 15.4890(3) _cell_length_b 7.7878(1) _cell_length_c 15.7930(3) _cell_angle_alpha 90.00 _cell_angle_beta 101.341(1) _cell_angle_gamma 90.00 _cell_volume 1867.84(6) _cell_formula_units_Z 4 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used 6739 _cell_measurement_theta_min 2.63 _cell_measurement_theta_max 29.30 _exptl_crystal_description 'hexagonal blocks' _exptl_crystal_colour 'colorless' _exptl_crystal_size_max 0.33 _exptl_crystal_size_mid 0.25 _exptl_crystal_size_min 0.23 _exptl_crystal_density_meas 'not measured' _exptl_crystal_density_diffrn 1.389 _exptl_crystal_density_method ? _exptl_crystal_F_000 824 _exptl_absorpt_coefficient_mu 0.508 _exptl_absorpt_correction_type 'sadabs (Sheldrick, 1996)' _exptl_absorpt_correction_T_min 0.7940 _exptl_absorpt_correction_T_max 0.9111 _exptl_special_details ; ? ; _diffrn_ambient_temperature 293(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 'Siemens SMART CCD System' _diffrn_measurement_method 'frames \w scans' _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 11341 _diffrn_reflns_av_R_equivalents 0.0227 _diffrn_reflns_av_sigmaI/netI 0.0319 _diffrn_reflns_limit_h_min -11 _diffrn_reflns_limit_h_max 21 _diffrn_reflns_limit_k_min -10 _diffrn_reflns_limit_k_max 10 _diffrn_reflns_limit_l_min -21 _diffrn_reflns_limit_l_max 15 _diffrn_reflns_theta_min 2.63 _diffrn_reflns_theta_max 29.30 _reflns_number_total 4566 _reflns_number_observed 3713 _reflns_observed_criterion >2sigma(I) _computing_data_collection 'SMART (Siemens, 1996)' _computing_cell_refinement 'SAINT (Siemens, 1996)' _computing_data_reduction 'SAINT (Siemens, 1996)' _computing_structure_solution 'SHELXS-86 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXTL (Siemens, 1996)' _computing_molecular_graphics 'SHELXTL (Siemens, 1996)' _computing_publication_material 'SHELXTL (Siemens, 1996)' _refine_special_details ; Refinement on F^2^ for ALL reflections except for 0 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. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme 'calc w=1/[\s^2^(Fo^2^)+(0.0405P)^2^+1.9758P] 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 ; riding models ; _refine_ls_extinction_method SHELXL _refine_ls_extinction_coef 0.0020(6) _refine_ls_extinction_expression 'Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^' _refine_ls_number_reflns 4566 _refine_ls_number_parameters 218 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0630 _refine_ls_R_factor_obs 0.0484 _refine_ls_wR_factor_all 0.1153 _refine_ls_wR_factor_obs 0.1079 _refine_ls_goodness_of_fit_all 1.045 _refine_ls_goodness_of_fit_obs 1.089 _refine_ls_restrained_S_all 1.045 _refine_ls_restrained_S_obs 1.089 _refine_ls_shift/esd_max -0.001 _refine_ls_shift/esd_mean 0.000 _refine_diff_density_max 1.011 _refine_diff_density_min -0.891 _refine_diff_density_rms 0.061 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 S1 S 0.00185(4) 0.27247(7) 0.46308(4) 0.03113(14) Uani 1 d . . S2 S 0.12644(4) 0.05936(8) 0.58828(4) 0.0356(2) Uani 1 d . . C1 C 0.04067(13) 0.0513(3) 0.48857(12) 0.0244(4) Uani 1 d . . C2 C 0.07612(13) -0.0304(3) 0.41357(14) 0.0270(4) Uani 1 d . . C3 C 0.14140(15) -0.1560(3) 0.4278(2) 0.0350(5) Uani 1 d . . H3 H 0.16533(15) -0.1894(3) 0.4840(2) 0.042 Uiso 1 calc R . C4 C 0.1714(2) -0.2323(3) 0.3595(2) 0.0453(6) Uani 1 d . . H4 H 0.2150(2) -0.3160(3) 0.3704(2) 0.054 Uiso 1 calc R . C5 C 0.1369(2) -0.1844(4) 0.2757(2) 0.0508(7) Uani 1 d . . H5 H 0.1565(2) -0.2365(4) 0.2300(2) 0.061 Uiso 1 calc R . C6 C 0.0730(2) -0.0586(4) 0.2602(2) 0.0472(6) Uani 1 d . . H6 H 0.0501(2) -0.0247(4) 0.2038(2) 0.057 Uiso 1 calc R . C7 C 0.0426(2) 0.0178(3) 0.32835(14) 0.0351(5) Uani 1 d . . H7 H -0.0006(2) 0.1022(3) 0.31699(14) 0.042 Uiso 1 calc R . C8 C 0.1020(2) 0.3717(3) 0.4438(2) 0.0371(5) Uani 1 d . . H8A H 0.1213(2) 0.3111(3) 0.3972(2) 0.045 Uiso 1 calc R . H8B H 0.0891(2) 0.4892(3) 0.4251(2) 0.045 Uiso 1 calc R . C9 C 0.1762(2) 0.3724(3) 0.5219(2) 0.0449(6) Uani 1 d . . H9A H 0.1565(2) 0.4304(3) 0.5691(2) 0.054 Uiso 1 calc R . H9B H 0.2252(2) 0.4372(3) 0.5084(2) 0.054 Uiso 1 calc R . C10 C 0.2079(2) 0.1928(3) 0.5514(2) 0.0411(6) Uani 1 d . . H10A H 0.2588(2) 0.2034(3) 0.5979(2) 0.049 Uiso 1 calc R . H10B H 0.2269(2) 0.1350(3) 0.5038(2) 0.049 Uiso 1 calc R . S3 S 0.44986(5) 0.37621(11) 0.60658(5) 0.0555(2) Uani 1 d . . S4 S 0.40219(5) 0.70087(11) 0.50926(5) 0.0595(2) Uani 1 d . . C11 C 0.49119(14) 0.5451(3) 0.54276(13) 0.0310(5) Uani 1 d . . C12 C 0.57442(14) 0.6302(3) 0.59510(14) 0.0310(5) Uani 1 d . . C13 C 0.5954(2) 0.8004(4) 0.5813(2) 0.0467(6) Uani 1 d . . H13 H 0.5578(2) 0.8652(4) 0.5403(2) 0.056 Uiso 1 calc R . C14 C 0.6714(2) 0.8743(5) 0.6275(2) 0.0641(10) Uani 1 d . . H14 H 0.6841(2) 0.9882(5) 0.6173(2) 0.077 Uiso 1 calc R . C15 C 0.7278(2) 0.7824(5) 0.6880(2) 0.0695(11) Uani 1 d . . H15 H 0.7788(2) 0.8330(5) 0.7187(2) 0.083 Uiso 1 calc R . C16 C 0.7087(2) 0.6157(5) 0.7030(2) 0.0633(10) Uani 1 d . . H16 H 0.7471(2) 0.5525(5) 0.7440(2) 0.076 Uiso 1 calc R . C17 C 0.6323(2) 0.5389(4) 0.6575(2) 0.0449(6) Uani 1 d . . H17 H 0.6198(2) 0.4255(4) 0.6691(2) 0.054 Uiso 1 calc R . C18 C 0.4282(2) 0.5019(6) 0.6961(2) 0.0741(12) Uani 1 d . . H18A H 0.4105(2) 0.4250(6) 0.7379(2) 0.089 Uiso 1 calc R . H18B H 0.4824(2) 0.5575(6) 0.7240(2) 0.089 Uiso 1 calc R . C19 C 0.3589(2) 0.6356(7) 0.6719(3) 0.089(2) Uani 1 d . . H19A H 0.3467(2) 0.6878(7) 0.7241(3) 0.107 Uiso 1 calc R . H19B H 0.3051(2) 0.5810(7) 0.6421(3) 0.107 Uiso 1 calc R . C20 C 0.3846(2) 0.7754(5) 0.6144(2) 0.0792(13) Uani 1 d . . H20A H 0.4382(2) 0.8297(5) 0.6446(2) 0.095 Uiso 1 calc R . H20B H 0.3387(2) 0.8620(5) 0.6051(2) 0.095 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 S1 0.0331(3) 0.0231(3) 0.0392(3) 0.0019(2) 0.0122(2) 0.0009(2) S2 0.0308(3) 0.0451(3) 0.0282(3) 0.0027(2) -0.0007(2) -0.0094(2) C1 0.0251(9) 0.0244(10) 0.0230(9) -0.0001(7) 0.0031(8) -0.0018(8) C2 0.0257(10) 0.0245(10) 0.0316(10) -0.0029(8) 0.0071(8) -0.0035(8) C3 0.0309(11) 0.0297(11) 0.0460(13) 0.0017(10) 0.0118(10) -0.0007(9) C4 0.0377(13) 0.0322(12) 0.072(2) -0.0125(12) 0.0254(13) -0.0022(10) C5 0.0480(15) 0.052(2) 0.059(2) -0.0290(14) 0.0274(14) -0.0134(13) C6 0.0486(15) 0.060(2) 0.0345(13) -0.0149(12) 0.0113(11) -0.0120(13) C7 0.0344(11) 0.0406(13) 0.0302(11) -0.0036(9) 0.0059(9) -0.0010(10) C8 0.0416(13) 0.0276(11) 0.0455(13) 0.0010(10) 0.0168(11) -0.0075(10) C9 0.0434(14) 0.0405(14) 0.053(2) -0.0079(11) 0.0145(12) -0.0179(11) C10 0.0300(11) 0.0498(15) 0.0427(13) -0.0016(11) 0.0055(10) -0.0120(11) S3 0.0654(5) 0.0643(5) 0.0414(4) -0.0080(3) 0.0218(3) -0.0330(4) S4 0.0472(4) 0.0719(5) 0.0518(4) -0.0178(4) -0.0085(3) 0.0265(4) C11 0.0278(10) 0.0367(12) 0.0281(11) -0.0020(9) 0.0042(8) -0.0007(9) C12 0.0283(10) 0.0359(12) 0.0288(10) -0.0045(9) 0.0055(8) -0.0029(9) C13 0.060(2) 0.0445(15) 0.0371(13) -0.0052(11) 0.0136(12) -0.0150(13) C14 0.073(2) 0.070(2) 0.059(2) -0.028(2) 0.035(2) -0.041(2) C15 0.0369(15) 0.103(3) 0.073(2) -0.054(2) 0.021(2) -0.027(2) C16 0.0390(15) 0.091(3) 0.051(2) -0.033(2) -0.0117(13) 0.016(2) C17 0.0429(14) 0.0476(15) 0.0392(13) -0.0083(11) -0.0038(11) 0.0053(12) C18 0.069(2) 0.116(3) 0.047(2) -0.027(2) 0.033(2) -0.042(2) C19 0.058(2) 0.149(4) 0.070(2) -0.061(3) 0.036(2) -0.035(3) C20 0.054(2) 0.100(3) 0.077(2) -0.050(2) -0.001(2) 0.024(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 C8 1.811(2) . ? S1 C1 1.842(2) . ? S2 C10 1.817(2) . ? S2 C1 1.851(2) . ? C1 C2 1.538(3) . ? C1 C1 1.592(4) 3_556 ? C2 C3 1.393(3) . ? C2 C7 1.395(3) . ? C3 C4 1.388(3) . ? C4 C5 1.378(4) . ? C5 C6 1.380(4) . ? C6 C7 1.391(3) . ? C8 C9 1.512(4) . ? C9 C10 1.525(4) . ? S3 C18 1.804(3) . ? S3 C11 1.846(2) . ? S4 C20 1.829(3) . ? S4 C11 1.834(2) . ? C11 C12 1.538(3) . ? C11 C11 1.593(4) 3_666 ? C12 C17 1.390(3) . ? C12 C13 1.392(4) . ? C13 C14 1.382(4) . ? C14 C15 1.364(5) . ? C15 C16 1.362(5) . ? C16 C17 1.393(4) . ? C18 C19 1.490(6) . ? C19 C20 1.520(6) . ? 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 C8 S1 C1 100.48(10) . . ? C10 S2 C1 100.04(10) . . ? C2 C1 C1 112.6(2) . 3_556 ? C2 C1 S1 111.67(13) . . ? C1 C1 S1 106.3(2) 3_556 . ? C2 C1 S2 111.34(14) . . ? C1 C1 S2 107.0(2) 3_556 . ? S1 C1 S2 107.65(10) . . ? C3 C2 C7 117.7(2) . . ? C3 C2 C1 121.6(2) . . ? C7 C2 C1 120.7(2) . . ? C4 C3 C2 121.3(2) . . ? C5 C4 C3 120.3(2) . . ? C4 C5 C6 119.5(2) . . ? C5 C6 C7 120.4(3) . . ? C6 C7 C2 120.9(2) . . ? C9 C8 S1 113.8(2) . . ? C8 C9 C10 113.2(2) . . ? C9 C10 S2 114.8(2) . . ? C18 S3 C11 100.33(15) . . ? C20 S4 C11 100.71(14) . . ? C12 C11 C11 112.4(2) . 3_666 ? C12 C11 S4 111.9(2) . . ? C11 C11 S4 106.9(2) 3_666 . ? C12 C11 S3 110.94(15) . . ? C11 C11 S3 106.5(2) 3_666 . ? S4 C11 S3 107.88(11) . . ? C17 C12 C13 117.4(2) . . ? C17 C12 C11 121.1(2) . . ? C13 C12 C11 121.5(2) . . ? C14 C13 C12 121.0(3) . . ? C15 C14 C13 120.9(3) . . ? C16 C15 C14 119.4(3) . . ? C15 C16 C17 120.7(3) . . ? C12 C17 C16 120.7(3) . . ? C19 C18 S3 114.4(2) . . ? C18 C19 C20 113.2(3) . . ? C19 C20 S4 114.7(3) . . ? 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 C8 S1 C1 C2 -59.3(2) . . . . ? C8 S1 C1 C1 177.6(2) . . . 3_556 ? C8 S1 C1 S2 63.25(12) . . . . ? C10 S2 C1 C2 60.7(2) . . . . ? C10 S2 C1 C1 -175.9(2) . . . 3_556 ? C10 S2 C1 S1 -62.04(13) . . . . ? C1 C1 C2 C3 -89.3(3) 3_556 . . . ? S1 C1 C2 C3 151.2(2) . . . . ? S2 C1 C2 C3 30.8(2) . . . . ? C1 C1 C2 C7 89.8(3) 3_556 . . . ? S1 C1 C2 C7 -29.7(2) . . . . ? S2 C1 C2 C7 -150.1(2) . . . . ? C7 C2 C3 C4 -0.8(3) . . . . ? C1 C2 C3 C4 178.3(2) . . . . ? C2 C3 C4 C5 0.1(4) . . . . ? C3 C4 C5 C6 0.8(4) . . . . ? C4 C5 C6 C7 -0.9(4) . . . . ? C5 C6 C7 C2 0.2(4) . . . . ? C3 C2 C7 C6 0.6(3) . . . . ? C1 C2 C7 C6 -178.5(2) . . . . ? C1 S1 C8 C9 -62.8(2) . . . . ? S1 C8 C9 C10 64.2(3) . . . . ? C8 C9 C10 S2 -63.7(3) . . . . ? C1 S2 C10 C9 60.8(2) . . . . ? C20 S4 C11 C12 -61.5(2) . . . . ? C20 S4 C11 C11 175.1(2) . . . 3_666 ? C20 S4 C11 S3 60.8(2) . . . . ? C18 S3 C11 C12 60.4(2) . . . . ? C18 S3 C11 C11 -177.0(2) . . . 3_666 ? C18 S3 C11 S4 -62.5(2) . . . . ? C11 C11 C12 C17 -89.0(3) 3_666 . . . ? S4 C11 C12 C17 150.7(2) . . . . ? S3 C11 C12 C17 30.1(3) . . . . ? C11 C11 C12 C13 90.3(3) 3_666 . . . ? S4 C11 C12 C13 -30.1(3) . . . . ? S3 C11 C12 C13 -150.6(2) . . . . ? C17 C12 C13 C14 0.6(4) . . . . ? C11 C12 C13 C14 -178.7(2) . . . . ? C12 C13 C14 C15 0.0(4) . . . . ? C13 C14 C15 C16 -0.2(5) . . . . ? C14 C15 C16 C17 -0.3(5) . . . . ? C13 C12 C17 C16 -1.0(4) . . . . ? C11 C12 C17 C16 178.3(2) . . . . ? C15 C16 C17 C12 0.9(4) . . . . ? C11 S3 C18 C19 63.3(3) . . . . ? S3 C18 C19 C20 -65.1(4) . . . . ? C18 C19 C20 S4 62.8(4) . . . . ? C11 S4 C20 C19 -59.5(3) . . . . ? #===END data_2,2'-diphenyl-2,2'-bis(1,3-dioxolanyl) #2 _audit_creation_method SHELXL _chemical_name_systematic ; 2,2'-diphenyl-2,2'-bis(1,3-dioxolanyl) ; _chemical_name_common ? _chemical_formula_moiety ? _chemical_formula_structural ? _chemical_formula_analytical ? _chemical_formula_sum 'C18 H18 O4' _chemical_formula_weight 298.32 _chemical_melting_point 230.0oC _chemical_compound_source 'see text' loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source 'C' 'C' 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 'H' 'H' 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 'O' 'O' 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting 'monoclinic' _symmetry_space_group_name_H-M 'P2(1)/n' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, y+1/2, -z+1/2' '-x, -y, -z' 'x-1/2, -y-1/2, z-1/2' _cell_length_a 6.0592(3) _cell_length_b 6.9442(4) _cell_length_c 17.666(1) _cell_angle_alpha 90.00 _cell_angle_beta 94.023(1) _cell_angle_gamma 90.00 _cell_volume 741.50(7) _cell_formula_units_Z 2 _cell_measurement_temperature 296(2) _cell_measurement_reflns_used 2739 _cell_measurement_theta_min 2.31 _cell_measurement_theta_max 28.97 _exptl_crystal_description 'long thin plates cut' _exptl_crystal_colour 'colorless' _exptl_crystal_size_max 0.40 _exptl_crystal_size_mid 0.37 _exptl_crystal_size_min 0.15 _exptl_crystal_density_meas 'not measured' _exptl_crystal_density_diffrn 1.336 _exptl_crystal_density_method ? _exptl_crystal_F_000 316 _exptl_absorpt_coefficient_mu 0.094 _exptl_absorpt_correction_type 'SADABS (Sheldrick, 1996)' _exptl_absorpt_correction_T_min 0.7594 _exptl_absorpt_correction_T_max 0.9778 _exptl_special_details ; ? ; _diffrn_ambient_temperature 296(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 'Siemens SMART CCD System' _diffrn_measurement_method 'frames,\w scans' _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 4412 _diffrn_reflns_av_R_equivalents 0.0167 _diffrn_reflns_av_sigmaI/netI 0.0234 _diffrn_reflns_limit_h_min -7 _diffrn_reflns_limit_h_max 8 _diffrn_reflns_limit_k_min -9 _diffrn_reflns_limit_k_max 6 _diffrn_reflns_limit_l_min -24 _diffrn_reflns_limit_l_max 23 _diffrn_reflns_theta_min 2.31 _diffrn_reflns_theta_max 28.97 _reflns_number_total 1789 _reflns_number_observed 1415 _reflns_observed_criterion >2sigma(I) _computing_data_collection 'SMART (Siemens, 1996)' _computing_cell_refinement 'SAINT (Siemens, 1996)' _computing_data_reduction 'SAINT (Siemens, 1996)' _computing_structure_solution 'SHELXS-86 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXTL (Siemens, 1996)' _computing_molecular_graphics 'SHELXTL (Siemens, 1996)' _computing_publication_material 'SHELXTL (Siemens, 1996)' _refine_special_details ; Refinement on F^2^ for ALL reflections except for 0 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. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme 'calc w=1/[\s^2^(Fo^2^)+(0.0425P)^2^+0.1433P] 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 ; riding models ; _refine_ls_extinction_method SHELXL _refine_ls_extinction_coef 0.0075(38) _refine_ls_extinction_expression 'Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^' _refine_ls_number_reflns 1789 _refine_ls_number_parameters 101 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0526 _refine_ls_R_factor_obs 0.0389 _refine_ls_wR_factor_all 0.1021 _refine_ls_wR_factor_obs 0.0956 _refine_ls_goodness_of_fit_all 1.059 _refine_ls_goodness_of_fit_obs 1.123 _refine_ls_restrained_S_all 1.059 _refine_ls_restrained_S_obs 1.123 _refine_ls_shift/esd_max 0.000 _refine_ls_shift/esd_mean 0.000 _refine_diff_density_max 0.191 _refine_diff_density_min -0.156 _refine_diff_density_rms 0.031 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 O1 O 0.25562(14) 0.14616(14) 0.00796(5) 0.0433(3) Uani 1 d . . O2 O 0.60488(15) 0.20493(13) 0.05515(5) 0.0416(3) Uani 1 d . . C1 C 0.4551(2) 0.0542(2) 0.03403(6) 0.0344(3) Uani 1 d . . C2 C 0.2426(3) 0.3197(2) 0.05179(9) 0.0576(4) Uani 1 d . . H2A H 0.1341(3) 0.3065(2) 0.08927(9) 0.069 Uiso 1 calc R . H2B H 0.2020(3) 0.4283(2) 0.01922(9) 0.069 Uiso 1 calc R . C3 C 0.4716(3) 0.3468(2) 0.08984(8) 0.0540(4) Uani 1 d . . H3A H 0.5261(3) 0.4757(2) 0.08102(8) 0.065 Uiso 1 calc R . H3B H 0.4714(3) 0.3255(2) 0.14409(8) 0.065 Uiso 1 calc R . C4 C 0.4192(2) -0.0783(2) 0.10141(7) 0.0354(3) Uani 1 d . . C5 C 0.2162(2) -0.1676(2) 0.10792(8) 0.0436(3) Uani 1 d . . H5 H 0.1019(2) -0.1491(2) 0.07067(8) 0.052 Uiso 1 calc R . C6 C 0.1836(3) -0.2848(2) 0.17023(9) 0.0530(4) Uani 1 d . . H6 H 0.0479(3) -0.3452(2) 0.17415(9) 0.064 Uiso 1 calc R . C7 C 0.3508(3) -0.3117(2) 0.22587(8) 0.0576(4) Uani 1 d . . H7 H 0.3277(3) -0.3891(2) 0.26754(8) 0.069 Uiso 1 calc R . C8 C 0.5530(3) -0.2237(2) 0.21985(8) 0.0557(4) Uani 1 d . . H8 H 0.6660(3) -0.2420(2) 0.25756(8) 0.067 Uiso 1 calc R . C9 C 0.5887(2) -0.1075(2) 0.15746(7) 0.0446(3) Uani 1 d . . H9 H 0.7257(2) -0.0497(2) 0.15335(7) 0.054 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 O1 0.0437(5) 0.0470(5) 0.0386(5) -0.0020(4) -0.0003(4) 0.0157(4) O2 0.0486(5) 0.0366(5) 0.0399(5) -0.0090(4) 0.0061(4) -0.0037(4) C1 0.0347(6) 0.0353(6) 0.0328(6) -0.0038(5) 0.0001(4) 0.0041(5) C2 0.0667(10) 0.0461(8) 0.0612(9) -0.0054(7) 0.0138(7) 0.0182(7) C3 0.0781(10) 0.0380(7) 0.0469(8) -0.0094(6) 0.0108(7) 0.0055(7) C4 0.0416(6) 0.0352(6) 0.0297(6) -0.0041(5) 0.0045(5) 0.0039(5) C5 0.0454(7) 0.0441(7) 0.0421(7) -0.0046(5) 0.0074(5) 0.0005(6) C6 0.0633(9) 0.0418(8) 0.0571(9) -0.0031(6) 0.0256(7) -0.0030(7) C7 0.0915(12) 0.0413(8) 0.0426(8) 0.0063(6) 0.0226(8) 0.0093(8) C8 0.0776(11) 0.0535(9) 0.0349(7) 0.0042(6) -0.0025(7) 0.0144(8) C9 0.0505(8) 0.0458(7) 0.0367(7) -0.0002(5) -0.0022(5) 0.0030(6) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag O1 C1 1.4152(14) . ? O1 C2 1.437(2) . ? O2 C1 1.4185(15) . ? O2 C3 1.438(2) . ? C1 C4 1.532(2) . ? C1 C1 1.549(2) 3_655 ? C2 C3 1.510(2) . ? C4 C5 1.389(2) . ? C4 C9 1.391(2) . ? C5 C6 1.394(2) . ? C6 C7 1.374(2) . ? C7 C8 1.380(2) . ? C8 C9 1.395(2) . ? 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 C1 O1 C2 106.31(10) . . ? C1 O2 C3 104.46(10) . . ? O1 C1 O2 105.58(9) . . ? O1 C1 C4 111.06(9) . . ? O2 C1 C4 111.22(9) . . ? O1 C1 C1 107.77(11) . 3_655 ? O2 C1 C1 108.01(12) . 3_655 ? C4 C1 C1 112.86(12) . 3_655 ? O1 C2 C3 105.14(11) . . ? O2 C3 C2 104.51(11) . . ? C5 C4 C9 119.32(12) . . ? C5 C4 C1 120.47(11) . . ? C9 C4 C1 120.20(11) . . ? C4 C5 C6 120.08(13) . . ? C7 C6 C5 120.41(14) . . ? C6 C7 C8 119.92(14) . . ? C7 C8 C9 120.30(14) . . ? C4 C9 C8 119.96(14) . . ? 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 C2 O1 C1 O2 -32.73(12) . . . . ? C2 O1 C1 C4 87.93(13) . . . . ? C2 O1 C1 C1 -147.97(13) . . . 3_655 ? C3 O2 C1 O1 38.51(12) . . . . ? C3 O2 C1 C4 -82.05(11) . . . . ? C3 O2 C1 C1 153.58(12) . . . 3_655 ? C1 O1 C2 C3 14.08(15) . . . . ? C1 O2 C3 C2 -28.65(14) . . . . ? O1 C2 C3 O2 9.0(2) . . . . ? O1 C1 C4 C5 30.29(15) . . . . ? O2 C1 C4 C5 147.56(11) . . . . ? C1 C1 C4 C5 -90.86(15) 3_655 . . . ? O1 C1 C4 C9 -148.57(11) . . . . ? O2 C1 C4 C9 -31.30(15) . . . . ? C1 C1 C4 C9 90.3(2) 3_655 . . . ? C9 C4 C5 C6 0.1(2) . . . . ? C1 C4 C5 C6 -178.72(12) . . . . ? C4 C5 C6 C7 0.5(2) . . . . ? C5 C6 C7 C8 -0.6(2) . . . . ? C6 C7 C8 C9 0.0(2) . . . . ? C5 C4 C9 C8 -0.8(2) . . . . ? C1 C4 C9 C8 178.10(12) . . . . ? C7 C8 C9 C4 0.7(2) . . . . ?