# Supplementary Material (ESI) for Chemical Communications # This journal is © The Royal Society of Chemistry 2006 data_global _journal_name_full Chem.Commun. _journal_coden_Cambridge 0182 _publ_contact_author_name 'Holger Butenschon' _publ_contact_author_address ; Institut fur Organische Chemie Universitat Hannover Schneiderberg 1B Hannover D-30167 GERMANY ; _publ_contact_author_email HOLGER.BUTENSCHOEN@MBOX.OCI.UNI-HANNOVER.DE _publ_contact_letter ; Please consider this CIF submission as supplementary material to the following publication : ; _publ_section_title ; Unanticipated Formation of ortho Sulfone Substituted Phenols by Anionic Thia-Fries Rearrangement of Aryl Triflate Tricarbonylchromium Complexes ; loop_ _publ_author_name _publ_author_address 'Zhao, Z.' ; Institut fur Organische Chemie Universitat Hannover Schneiderberg 1B D-30167 Hannover ; J.Messinger ; Solvay Pharmaceuticals GmbH Hans-Boeckler-Allee 20 D-30173 Hannover ; U.Schon ; Solvay Pharmaceuticals GmbH Hans-Boeckler-Allee 20 D-30173 Hannover ; R.Wartchow ; Institut fur Anorganische Chemie Universitat Hannover Callinstr. 9 D-30167 Hannover ; H.Butenschon ; Institut fur Organische Chemie Universitat Hannover Schneiderberg 1B D-30167 Hannover E-mail: holger.butenschoen@mbox.oci.uni-hannover.de ; _publ_section_abstract ; see paper ; _publ_section_comment ; The following crystal data belong to compound 17-THF in the paper ; _publ_section_experimental ; see paper ; _publ_section_references ; Sheldrick, G. M.: SHELXS-86, program for crystal structure determination University of Gottingen, 1990 Sheldrick, G. M.: SHELXL-97, program for refining crystal structures University of Gottingen, 1997 Sheldrick, G. M.: CIFTAB, program preparing tables from a CIF University of Gottingen, 1993 Spek, A. L.: PLATON, an integrated tool for the analysis of the results of a single crystal structure determination. Acta Crystallogr. Suppl. A46(1990)C-34 IPDS V2.93, X-RED, X-SHAPE, program packages for processing the data collected with Stoe diffractometers Fa. Stoe, Darmstadt, 1996, 1999 Further references in the paper ; _publ_section_figure_captions ; see paper ; _publ_section_acknowledgements ; The crystallographic work was supported by Prof. Dr. M. Binnewies, Institut fuer Anorganische Chemie der Universitaet Hannover. Computing facilities of RRZN (Hannover) were used. ; data_wart_zhzh2a _database_code_depnum_ccdc_archive 'CCDC 600472' _audit_creation_method SHELXL-97 _chemical_name_systematic ; Tricarbonyl(2-trifluoromethylsulfonylphenol)chromium(0) tetrahydrofurane solvate ; _chemical_name_common ;Tricarbonyl(2-trifluoromethylsulfonylphenol)chromium(0) tetrahydrofurane solvate ; _chemical_melting_point ? _chemical_formula_moiety 'C10 H5 Cr1 F3 O6 S1, C4 H8 O1' _chemical_formula_sum 'C14 H13 Cr F3 O7 S' _chemical_formula_weight 434.30 _chemical_compound_source 'synthetic ' 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' Cr Cr 0.3209 0.6236 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' F F 0.0171 0.0103 '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 'P 21/c' _symmetry_Int_Tables_number 14 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 6.519(3) _cell_length_b 17.392(7) _cell_length_c 16.169(8) _cell_angle_alpha 90.00 _cell_angle_beta 101.43(5) _cell_angle_gamma 90.00 _cell_volume 1796.9(14) _cell_formula_units_Z 4 _cell_measurement_temperature 307(2) _cell_measurement_reflns_used 4414 _cell_measurement_theta_min 2.35 _cell_measurement_theta_max 19.8 _exptl_crystal_description 'irregular shape' _exptl_crystal_colour orange _exptl_crystal_size_max 0.44 _exptl_crystal_size_mid 0.41 _exptl_crystal_size_min 0.26 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.605 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 880 _exptl_absorpt_coefficient_mu 0.815 _exptl_absorpt_correction_type none _exptl_absorpt_correction_T_min 1.0 _exptl_absorpt_correction_T_max 1.0 _exptl_absorpt_process_details none _exptl_special_details ; IPDS measurement on 3.6.2003. Short descriptions of the IPDS are given in (e.g.) : Schuett W et al., J. Organomet. Chem. 443 (1993) C33-C36 and Sheldrick G M et al., Acta Crystallogr. B51 (1995) 89-98. Completeness of unique data set 100 %. 0 overloaded reflections. 1 overlapped reflection omitted, many further overlaps ignored due to an unresolved twin problem, for this reason many reflection intensities are erraneous and R-values are unsatisfying. 25380 measured reflections including unobserved and forbidden ones. 14 systematic absence violations. 14 forbidden reflections with 32\s(I)). R~int~ of the observed reflections is 0.13. Possible hydrogen bonds : O1-H1...O1', O1' belongs to the THF solvate molecule. Decay correction was necessary because of loss of solvate molecules. chemical melting point not measured, decomposition ; _diffrn_ambient_temperature 307(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 'Stoe IPDS area detector diffractometer' _diffrn_measurement_method '240 exposures, \D \f 1.5 \%' _diffrn_detector_area_resol_mean ? _diffrn_standards_number 0 _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% 46 _diffrn_reflns_number 24868 _diffrn_reflns_av_R_equivalents 0.2789 _diffrn_reflns_av_sigmaI/netI 0.2750 _diffrn_reflns_limit_h_min -8 _diffrn_reflns_limit_h_max 8 _diffrn_reflns_limit_k_min -21 _diffrn_reflns_limit_k_max 21 _diffrn_reflns_limit_l_min -20 _diffrn_reflns_limit_l_max 19 _diffrn_reflns_theta_min 2.34 _diffrn_reflns_theta_max 26.29 _reflns_number_total 3537 _reflns_number_gt 883 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Stoe IPDS software' _computing_cell_refinement 'Stoe IPDS software' _computing_data_reduction 'Stoe IPDS software and SHELXL-97' _computing_structure_solution 'SHELXS-86 (Sheldrick, 1986)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'PLATON (Spek, 1990)' _computing_publication_material ; The first CIF was issued by SHELXL-97. The edited CIF is finally treated with the program CIF2SX written by L. Farrugia, Univ. of Glasgow (1997) and a refinement cycle is repeated to assure that essential parameters were not changed. ; _refine_special_details ; Last refinement cycle on 12.5.2006 at 15:45. Distance restraints were applied to O1-H1---O1'. Only the heavier atoms Cr, S, F, and O were refined anisotropically because of the small amount of observed reflections in the data set. Anisotropic refinement of C atoms is possible in the sense that they don't become non positive definite, but the direction of longest half axes of the ellipsoids is not reasonable for some atoms. 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^)+(0.0100P)^2^] 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 3537 _refine_ls_number_parameters 169 _refine_ls_number_restraints 2 _refine_ls_R_factor_all 0.2711 _refine_ls_R_factor_gt 0.1099 _refine_ls_wR_factor_ref 0.1915 _refine_ls_wR_factor_gt 0.1725 _refine_ls_goodness_of_fit_ref 1.067 _refine_ls_restrained_S_all 1.067 _refine_ls_shift/su_max 0.000 _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 Cr Cr 0.4880(4) 0.34564(12) 0.00114(13) 0.0670(7) Uani 1 1 d . . . S S 0.1944(6) 0.2719(3) -0.1891(2) 0.0810(12) Uani 1 1 d . . . F1 F -0.1002(15) 0.2219(7) -0.3042(5) 0.152(4) Uani 1 1 d . . . F2 F -0.0848(16) 0.1681(7) -0.1813(6) 0.163(4) Uani 1 1 d . . . F3 F -0.2100(16) 0.2747(8) -0.1989(6) 0.161(4) Uani 1 1 d . . . O1 O 0.2832(15) 0.1690(5) -0.0332(5) 0.086(3) Uani 1 1 d D . . H1 H 0.320(14) 0.127(2) 0.002(3) 0.06(4) Uiso 1 1 d D . . O2 O 0.1847(16) 0.3411(7) -0.2340(5) 0.119(4) Uani 1 1 d . . . O3 O 0.3410(16) 0.2128(6) -0.1959(5) 0.108(3) Uani 1 1 d . . . O4 O 0.7811(14) 0.4405(5) 0.1249(5) 0.095(3) Uani 1 1 d . . . O5 O 0.6596(14) 0.4360(5) -0.1275(5) 0.099(3) Uani 1 1 d . . . O6 O 0.8136(14) 0.2208(6) 0.0036(5) 0.090(3) Uani 1 1 d . . . C1 C 0.2669(19) 0.2419(9) -0.0141(8) 0.075(4) Uiso 1 1 d . . . C2 C 0.2113(16) 0.2964(7) -0.0803(6) 0.051(3) Uiso 1 1 d . . . C3 C 0.1707(17) 0.3705(7) -0.0646(7) 0.067(3) Uiso 1 1 d . . . H2 H 0.1292 0.4029 -0.1106 0.080 Uiso 1 1 calc R . . C4 C 0.1874(17) 0.4029(8) 0.0186(7) 0.077(4) Uiso 1 1 d . . . H3 H 0.1519 0.4533 0.0288 0.092 Uiso 1 1 calc R . . C5 C 0.2656(17) 0.3478(8) 0.0840(6) 0.071(3) Uiso 1 1 d . . . H4 H 0.2961 0.3650 0.1395 0.085 Uiso 1 1 calc R . . C6 C 0.2973(17) 0.2720(7) 0.0691(6) 0.057(3) Uiso 1 1 d . . . H5 H 0.3401 0.2392 0.1146 0.069 Uiso 1 1 calc R . . C7 C -0.055(3) 0.2303(12) -0.2179(11) 0.107(5) Uiso 1 1 d . . . C8 C 0.672(2) 0.3981(8) 0.0758(8) 0.069(4) Uiso 1 1 d . . . C9 C 0.5924(19) 0.4024(8) -0.0806(7) 0.073(4) Uiso 1 1 d . . . C10 C 0.698(2) 0.2693(9) 0.0015(7) 0.067(4) Uiso 1 1 d . . . O1' O 0.437(2) 0.0783(7) 0.0936(8) 0.152(4) Uani 1 1 d D . . C1' C 0.638(4) 0.0804(14) 0.1315(13) 0.172(9) Uiso 1 1 d . . . H6 H 0.6643 0.1207 0.1737 0.207 Uiso 1 1 calc R . . H7 H 0.7277 0.0883 0.0910 0.207 Uiso 1 1 calc R . . C2' C 0.672(3) 0.0036(16) 0.1707(12) 0.189(7) Uiso 1 1 d . . . H8 H 0.7435 -0.0296 0.1375 0.227 Uiso 1 1 calc R . . H9 H 0.7561 0.0076 0.2271 0.227 Uiso 1 1 calc R . . C3' C 0.465(3) -0.0279(11) 0.1741(10) 0.149(7) Uiso 1 1 d . . . H10 H 0.4551 -0.0812 0.1560 0.179 Uiso 1 1 calc R . . H11 H 0.4383 -0.0248 0.2308 0.179 Uiso 1 1 calc R . . C4' C 0.318(3) 0.0199(14) 0.1163(12) 0.177(8) Uiso 1 1 d . . . H12 H 0.2514 -0.0095 0.0672 0.212 Uiso 1 1 calc R . . H13 H 0.2102 0.0400 0.1441 0.212 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 Cr 0.0729(14) 0.0770(13) 0.0542(9) 0.0034(15) 0.0201(8) 0.0071(17) S 0.081(3) 0.103(3) 0.059(2) -0.007(2) 0.0127(18) -0.010(3) F1 0.174(10) 0.195(11) 0.082(6) -0.050(7) 0.015(6) -0.013(8) F2 0.169(9) 0.142(10) 0.174(9) 0.007(8) 0.025(6) -0.063(9) F3 0.112(8) 0.214(13) 0.143(7) -0.005(8) -0.005(6) 0.000(8) O1 0.125(8) 0.053(7) 0.083(6) -0.016(5) 0.030(5) -0.006(6) O2 0.200(11) 0.090(7) 0.065(5) 0.016(6) 0.021(6) -0.024(8) O3 0.121(8) 0.139(9) 0.073(6) -0.017(6) 0.042(6) 0.026(8) O4 0.108(8) 0.094(7) 0.083(6) -0.005(6) 0.020(5) -0.030(6) O5 0.115(8) 0.094(8) 0.103(7) -0.002(6) 0.060(6) -0.019(6) O6 0.089(7) 0.096(8) 0.098(6) -0.011(5) 0.047(5) 0.010(6) O1' 0.173(13) 0.096(10) 0.192(12) 0.032(8) 0.047(10) -0.013(9) _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 Cr C8 1.776(14) . ? Cr C9 1.882(13) . ? Cr C10 1.904(15) . ? Cr C5 2.160(10) . ? Cr C3 2.173(12) . ? Cr C2 2.186(11) . ? Cr C6 2.221(11) . ? Cr C4 2.264(12) . ? Cr C1 2.292(15) . ? S O2 1.401(10) . ? S O3 1.422(10) . ? S C7 1.755(19) . ? S C2 1.792(10) . ? F1 C7 1.376(16) . ? F2 C7 1.266(18) . ? F3 C7 1.355(17) . ? O1 C1 1.314(15) . ? O4 C8 1.207(13) . ? O5 C9 1.114(12) . ? O6 C10 1.129(13) . ? C1 C6 1.420(14) . ? C1 C2 1.422(15) . ? C2 C3 1.350(13) . ? C3 C4 1.442(13) . ? C4 C5 1.443(15) . ? C5 C6 1.362(16) . ? O1' C1' 1.335(19) . ? O1' C4' 1.37(2) . ? C1' C2' 1.48(3) . ? C2' C3' 1.46(2) . ? C3' C4' 1.46(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 C8 Cr C9 85.3(6) . . ? C8 Cr C10 88.2(6) . . ? C9 Cr C10 90.5(6) . . ? C8 Cr C5 90.9(5) . . ? C9 Cr C5 143.8(6) . . ? C10 Cr C5 125.4(5) . . ? C8 Cr C3 132.8(5) . . ? C9 Cr C3 89.6(5) . . ? C10 Cr C3 138.8(5) . . ? C5 Cr C3 67.0(4) . . ? C8 Cr C2 167.4(5) . . ? C9 Cr C2 98.8(5) . . ? C10 Cr C2 103.5(5) . . ? C5 Cr C2 78.8(4) . . ? C3 Cr C2 36.1(4) . . ? C8 Cr C6 109.2(5) . . ? C9 Cr C6 164.9(5) . . ? C10 Cr C6 93.9(5) . . ? C5 Cr C6 36.2(4) . . ? C3 Cr C6 77.6(4) . . ? C2 Cr C6 66.2(4) . . ? C8 Cr C4 100.0(5) . . ? C9 Cr C4 107.4(5) . . ? C10 Cr C4 160.7(5) . . ? C5 Cr C4 38.0(4) . . ? C3 Cr C4 37.9(3) . . ? C2 Cr C4 67.4(4) . . ? C6 Cr C4 67.0(4) . . ? C8 Cr C1 143.4(5) . . ? C9 Cr C1 130.2(5) . . ? C10 Cr C1 83.5(5) . . ? C5 Cr C1 66.1(5) . . ? C3 Cr C1 65.6(4) . . ? C2 Cr C1 36.9(4) . . ? C6 Cr C1 36.6(4) . . ? C4 Cr C1 79.5(5) . . ? O2 S O3 122.8(6) . . ? O2 S C7 105.8(8) . . ? O3 S C7 106.5(8) . . ? O2 S C2 107.0(6) . . ? O3 S C2 109.6(5) . . ? C7 S C2 103.4(7) . . ? O1 C1 C6 125.2(12) . . ? O1 C1 C2 119.1(11) . . ? C6 C1 C2 115.7(13) . . ? O1 C1 Cr 134.9(10) . . ? C6 C1 Cr 68.9(7) . . ? C2 C1 Cr 67.5(7) . . ? C3 C2 C1 121.7(10) . . ? C3 C2 S 115.8(9) . . ? C1 C2 S 122.5(9) . . ? C3 C2 Cr 71.4(7) . . ? C1 C2 Cr 75.6(7) . . ? S C2 Cr 124.6(5) . . ? C2 C3 C4 124.5(11) . . ? C2 C3 Cr 72.5(7) . . ? C4 C3 Cr 74.5(6) . . ? C3 C4 C5 112.0(12) . . ? C3 C4 Cr 67.6(6) . . ? C5 C4 Cr 67.1(6) . . ? C6 C5 C4 123.8(11) . . ? C6 C5 Cr 74.3(7) . . ? C4 C5 Cr 74.9(6) . . ? C5 C6 C1 121.8(11) . . ? C5 C6 Cr 69.5(7) . . ? C1 C6 Cr 74.4(7) . . ? F2 C7 F3 101.0(15) . . ? F2 C7 F1 111.2(17) . . ? F3 C7 F1 105.7(15) . . ? F2 C7 S 116.6(14) . . ? F3 C7 S 113.4(14) . . ? F1 C7 S 108.3(12) . . ? O4 C8 Cr 172.7(11) . . ? O5 C9 Cr 178.0(12) . . ? O6 C10 Cr 175.6(12) . . ? C1' O1' C4' 117.0(17) . . ? O1' C1' C2' 102.8(19) . . ? C3' C2' C1' 107.2(19) . . ? C4' C3' C2' 105.0(18) . . ? O1' C4' C3' 104.9(16) . . ? _diffrn_measured_fraction_theta_max 0.973 _diffrn_reflns_theta_full 26.29 _diffrn_measured_fraction_theta_full 0.973 _refine_diff_density_max 0.553 _refine_diff_density_min -0.352 _refine_diff_density_rms 0.095 # _eof