# Electronic Supplementary Material (ESI) for Chemical Communications # This journal is © The Royal Society of Chemistry 2012 data_global _journal_name_full Chem.Commun. _journal_coden_cambridge 0182 _publ_contact_author # Name and address of author for correspondence ; Pr G. Evano Universit\'e Libre de Bruxelles Service de Chimie et PhysicoChimie Organiques Laboratoire de Chimie Organique Avenue F. D. Roosevelt 50 CP160/06 B-1050 Brussels Belgium ; _publ_contact_author_phone '(32) 2 650 30 57' _publ_contact_author_fax '(32) 2 650 27 98' _publ_contact_author_email gevano@ulb.ac.be _publ_requested_coeditor_name ? _publ_contact_letter ; ; #==================================================================== # 2. processing summary (iucr office use only) _journal_date_recd_electronic ? _journal_date_to_coeditor ? _journal_date_from_coeditor ? _journal_date_accepted ? _journal_date_printers_first ? _journal_date_printers_final ? _journal_date_proofs_out ? _journal_date_proofs_in ? _journal_coeditor_name ? _journal_coeditor_code ? _journal_coeditor_notes ; ; _journal_techeditor_code ? _journal_techeditor_notes ; ; _journal_coden_ASTM ? _journal_year ? _journal_volume ? _journal_issue ? _journal_page_first ? _journal_page_last ? _journal_suppl_publ_number ? _journal_suppl_publ_pages ? #==================================================================== # 3. title and author list _publ_section_title ; Stereoselective hydrofluorination of ynamides: a straightforward synthesis of novel \a-fluoroenamides ; # The loop structure below should contain the names and addresses of all # authors, in the required order of publication. Repeat as necessary. loop_ _publ_author_name _publ_author_address G.Compain ; Laboratoire Synth\`ese et r\'eactivit\'e des Substances naturelles UMR CNRS 6514, Universit\'e de Poitiers, Equipe Superacide 40, avenue du Recteur Pineau 86022 Poitiers Cedex France ; K.Jouvin ; Institut Lavoisier de Versailles, UMR CNRS 8180 Universit\'e de Versailles 45 Avenue des Etats Unis 78035 Versailles cedex France ; A.Martin-Mingot ; Laboratoire Synth\`ese et r\'eactivit\'e des Substances naturelles UMR CNRS 6514, Universit\'e de Poitiers, Equipe Superacide 40, avenue du Recteur Pineau 86022 Poitiers Cedex France ; G.Evano ; Universit\'e Libre de Bruxelles Service de Chimie et PhysicoChimie Organiques Laboratoire de Chimie Organique Avenue F. D. Roosevelt 50 CP160/06 B-1050 Brussels Belgium ; J.Marrot ; Institut Lavoisier de Versailles, UMR CNRS 8180 Universit\'e de Versailles 45 Avenue des Etats Unis 78035 Versailles cedex France ; ; S.Thibaudeau ; ; Laboratoire Synth\`ese et r\'eactivit\'e des Substances naturelles UMR CNRS 6514, Universit\'e de Poitiers, Equipe Superacide 40, avenue du Recteur Pineau 86022 Poitiers Cedex France ; #==================================================================== # 4. text _publ_section_abstract ; ; _publ_section_comment ; ; _publ_section_experimental ; ; _publ_section_references ; Sheldrick, G.M. (1993). SHELXL-93. Program for crystal structure determination. Univ. of G\"ottingen, Federal Republic of Germany. Sheldrick, G.M. (1997). SHELXS-86. Program for the solution of crystal structures. Univ. of G\"ottingen, Federal Republic of Germany. ; _publ_section_figure_captions ; ; _publ_section_acknowledgements ; ; _publ_contact_author_name 'Pr G. Evano' #==================================================================== data_1 _database_code_depnum_ccdc_archive 'CCDC 868335' #TrackingRef 'data12.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C21 H19 F N2 O2 S' _chemical_formula_weight 382.44 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' N N 0.0061 0.0033 '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' F F 0.0171 0.0103 '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 P2(1)/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 11.4189(10) _cell_length_b 14.9794(13) _cell_length_c 12.4070(9) _cell_angle_alpha 90.00 _cell_angle_beta 116.424(3) _cell_angle_gamma 90.00 _cell_volume 1900.5(3) _cell_formula_units_Z 4 _cell_measurement_temperature 150(2) _cell_measurement_reflns_used 9411 _cell_measurement_theta_min 2.41 _cell_measurement_theta_max 29.93 _exptl_crystal_description parallelepiped _exptl_crystal_colour colorless _exptl_crystal_size_max 0.28 _exptl_crystal_size_mid 0.20 _exptl_crystal_size_min 0.10 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.337 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 800 _exptl_absorpt_coefficient_mu 0.198 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.9466 _exptl_absorpt_correction_T_max 0.9805 _exptl_absorpt_process_details 'SADABS (Sheldrick, V2.10)' _exptl_special_details ; 'Blessing, Acta Cryst. (1995) A51, 33-38' ; _diffrn_ambient_temperature 150(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 'Bruker APEX-II CCD' _diffrn_measurement_method '\f and \w scans' _diffrn_detector_area_resol_mean 512x512 _diffrn_standards_number 0 _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 175446 _diffrn_reflns_av_R_equivalents 0.0271 _diffrn_reflns_av_sigmaI/netI 0.0075 _diffrn_reflns_limit_h_min -16 _diffrn_reflns_limit_h_max 16 _diffrn_reflns_limit_k_min -21 _diffrn_reflns_limit_k_max 21 _diffrn_reflns_limit_l_min -17 _diffrn_reflns_limit_l_max 17 _diffrn_reflns_theta_min 1.99 _diffrn_reflns_theta_max 30.00 _reflns_number_total 5522 _reflns_number_gt 5005 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker APEX2' _computing_cell_refinement 'Bruker SAINT' _computing_data_reduction 'Bruker SAINT' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Bruker SHELXTL' _computing_publication_material 'Bruker SHELXTL' _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^)+(0.0726P)^2^+0.5579P] 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_number_reflns 5522 _refine_ls_number_parameters 245 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0459 _refine_ls_R_factor_gt 0.0381 _refine_ls_wR_factor_ref 0.1220 _refine_ls_wR_factor_gt 0.1115 _refine_ls_goodness_of_fit_ref 1.062 _refine_ls_restrained_S_all 1.062 _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 S1 S 0.46980(3) 0.290687(18) 0.52467(2) 0.02636(9) Uani 1 1 d . . . O1 O 0.48519(9) 0.28876(6) 0.64581(8) 0.0347(2) Uani 1 1 d . . . O2 O 0.57876(8) 0.27408(7) 0.50001(9) 0.0370(2) Uani 1 1 d . . . F1 F 0.31535(8) 0.12487(7) 0.57826(9) 0.0567(3) Uani 1 1 d . . . N1 N -0.04275(10) 0.26277(7) 0.47442(9) 0.0301(2) Uani 1 1 d . . . C2 C -0.13767(13) 0.24572(9) 0.50654(12) 0.0362(3) Uani 1 1 d . . . H2 H -0.2075 0.2873 0.4835 0.043 Uiso 1 1 calc R . . C3 C -0.14057(14) 0.17128(11) 0.57128(14) 0.0434(3) Uani 1 1 d . . . H3 H -0.2110 0.1615 0.5909 0.052 Uiso 1 1 calc R . . C4 C -0.03799(14) 0.11148(11) 0.60659(14) 0.0455(3) Uani 1 1 d . . . H4 H -0.0361 0.0600 0.6521 0.055 Uiso 1 1 calc R . . C5 C 0.06218(12) 0.12740(9) 0.57482(12) 0.0359(3) Uani 1 1 d . . . H5 H 0.1336 0.0871 0.5982 0.043 Uiso 1 1 calc R . . C6 C 0.05644(11) 0.20356(7) 0.50796(10) 0.0251(2) Uani 1 1 d . . . C7 C 0.15378(10) 0.22692(7) 0.46542(9) 0.0253(2) Uani 1 1 d . . . H7 H 0.1301 0.2741 0.4084 0.030 Uiso 1 1 calc R . . C8 C 0.27016(11) 0.19088(8) 0.49612(10) 0.0271(2) Uani 1 1 d . . . N9 N 0.35973(10) 0.21243(6) 0.45169(9) 0.02627(19) Uani 1 1 d . . . C10 C 0.31896(13) 0.19997(8) 0.32091(10) 0.0307(2) Uani 1 1 d . . . H10A H 0.3891 0.2214 0.3011 0.037 Uiso 1 1 calc R . . H10B H 0.2393 0.2356 0.2739 0.037 Uiso 1 1 calc R . . C11 C 0.29172(11) 0.10295(8) 0.28741(9) 0.0260(2) Uani 1 1 d . . . C12 C 0.39195(11) 0.04046(8) 0.33697(11) 0.0315(2) Uani 1 1 d . . . H12 H 0.4770 0.0592 0.3927 0.038 Uiso 1 1 calc R . . C13 C 0.36837(14) -0.04910(9) 0.30554(12) 0.0381(3) Uani 1 1 d . . . H13 H 0.4373 -0.0914 0.3397 0.046 Uiso 1 1 calc R . . C14 C 0.24420(15) -0.07685(9) 0.22425(12) 0.0398(3) Uani 1 1 d . . . H14 H 0.2280 -0.1381 0.2028 0.048 Uiso 1 1 calc R . . C15 C 0.14446(13) -0.01532(10) 0.17469(11) 0.0403(3) Uani 1 1 d . . . H15 H 0.0595 -0.0343 0.1189 0.048 Uiso 1 1 calc R . . C16 C 0.16768(12) 0.07441(9) 0.20602(11) 0.0334(2) Uani 1 1 d . . . H16 H 0.0985 0.1164 0.1717 0.040 Uiso 1 1 calc R . . C17 C 0.39602(10) 0.39119(7) 0.45470(9) 0.0242(2) Uani 1 1 d . . . C18 C 0.41867(11) 0.42393(8) 0.36087(10) 0.0280(2) Uani 1 1 d . . . H18 H 0.4796 0.3954 0.3394 0.034 Uiso 1 1 calc R . . C19 C 0.35073(12) 0.49897(8) 0.29902(10) 0.0306(2) Uani 1 1 d . . . H19 H 0.3664 0.5221 0.2353 0.037 Uiso 1 1 calc R . . C20 C 0.26010(11) 0.54097(8) 0.32849(10) 0.0297(2) Uani 1 1 d . . . C21 C 0.24119(11) 0.50803(8) 0.42476(10) 0.0303(2) Uani 1 1 d . . . H21 H 0.1811 0.5371 0.4469 0.036 Uiso 1 1 calc R . . C22 C 0.30863(11) 0.43350(8) 0.48882(10) 0.0275(2) Uani 1 1 d . . . H22 H 0.2956 0.4117 0.5546 0.033 Uiso 1 1 calc R . . C23 C 0.18343(15) 0.61993(10) 0.25683(12) 0.0424(3) Uani 1 1 d . . . H23A H 0.2422 0.6711 0.2718 0.064 Uiso 1 1 calc R . . H23B H 0.1150 0.6350 0.2811 0.064 Uiso 1 1 calc R . . H23C H 0.1432 0.6052 0.1709 0.064 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 0.02201(14) 0.02961(15) 0.02923(15) 0.00224(9) 0.01300(11) 0.00276(9) O1 0.0336(4) 0.0403(5) 0.0274(4) 0.0033(3) 0.0111(3) 0.0028(3) O2 0.0249(4) 0.0404(5) 0.0512(5) 0.0041(4) 0.0220(4) 0.0058(3) F1 0.0391(4) 0.0729(6) 0.0706(6) 0.0506(5) 0.0355(4) 0.0259(4) N1 0.0279(4) 0.0284(5) 0.0364(5) -0.0002(4) 0.0165(4) 0.0020(4) C2 0.0324(6) 0.0385(6) 0.0444(7) 0.0024(5) 0.0231(5) 0.0064(5) C3 0.0374(6) 0.0547(8) 0.0502(7) 0.0117(6) 0.0303(6) 0.0059(6) C4 0.0397(7) 0.0532(8) 0.0529(8) 0.0234(7) 0.0289(6) 0.0080(6) C5 0.0286(5) 0.0411(6) 0.0411(6) 0.0147(5) 0.0182(5) 0.0065(5) C6 0.0223(4) 0.0284(5) 0.0246(5) -0.0006(4) 0.0104(4) -0.0007(4) C7 0.0249(5) 0.0254(5) 0.0259(5) 0.0022(4) 0.0116(4) -0.0008(4) C8 0.0274(5) 0.0301(5) 0.0266(5) 0.0063(4) 0.0144(4) 0.0025(4) N9 0.0287(4) 0.0278(4) 0.0278(4) 0.0000(3) 0.0175(4) -0.0015(3) C10 0.0403(6) 0.0293(5) 0.0277(5) 0.0026(4) 0.0197(5) 0.0002(4) C11 0.0281(5) 0.0302(5) 0.0236(4) 0.0017(4) 0.0151(4) -0.0007(4) C12 0.0272(5) 0.0359(6) 0.0306(5) -0.0009(4) 0.0121(4) 0.0019(4) C13 0.0451(7) 0.0339(6) 0.0390(6) 0.0016(5) 0.0221(5) 0.0074(5) C14 0.0563(8) 0.0346(6) 0.0366(6) -0.0056(5) 0.0280(6) -0.0107(6) C15 0.0367(6) 0.0524(8) 0.0314(6) -0.0035(5) 0.0150(5) -0.0167(6) C16 0.0262(5) 0.0449(7) 0.0290(5) 0.0060(4) 0.0123(4) -0.0002(5) C17 0.0215(4) 0.0261(5) 0.0258(4) -0.0014(4) 0.0114(4) -0.0011(4) C18 0.0288(5) 0.0306(5) 0.0293(5) -0.0026(4) 0.0171(4) -0.0027(4) C19 0.0365(6) 0.0312(5) 0.0256(5) -0.0005(4) 0.0150(4) -0.0036(4) C20 0.0289(5) 0.0288(5) 0.0254(5) -0.0018(4) 0.0066(4) -0.0010(4) C21 0.0276(5) 0.0317(5) 0.0328(5) -0.0023(4) 0.0144(4) 0.0028(4) C22 0.0270(5) 0.0306(5) 0.0288(5) -0.0005(4) 0.0158(4) 0.0007(4) C23 0.0444(7) 0.0379(7) 0.0357(6) 0.0059(5) 0.0094(5) 0.0090(5) _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 1.4291(9) . ? S1 O1 1.4337(9) . ? S1 N9 1.6616(10) . ? S1 C17 1.7547(11) . ? F1 C8 1.3471(13) . ? N1 C2 1.3354(16) . ? N1 C6 1.3502(14) . ? C2 C3 1.3833(19) . ? C2 H2 0.9500 . ? C3 C4 1.382(2) . ? C3 H3 0.9500 . ? C4 C5 1.3863(17) . ? C4 H4 0.9500 . ? C5 C6 1.3948(16) . ? C5 H5 0.9500 . ? C6 C7 1.4692(15) . ? C7 C8 1.3236(15) . ? C7 H7 0.9500 . ? C8 N9 1.3986(13) . ? N9 C10 1.4872(14) . ? C10 C11 1.5055(16) . ? C10 H10A 0.9900 . ? C10 H10B 0.9900 . ? C11 C16 1.3913(16) . ? C11 C12 1.3921(16) . ? C12 C13 1.3895(18) . ? C12 H12 0.9500 . ? C13 C14 1.388(2) . ? C13 H13 0.9500 . ? C14 C15 1.379(2) . ? C14 H14 0.9500 . ? C15 C16 1.392(2) . ? C15 H15 0.9500 . ? C16 H16 0.9500 . ? C17 C18 1.3895(15) . ? C17 C22 1.3974(14) . ? C18 C19 1.3872(16) . ? C18 H18 0.9500 . ? C19 C20 1.3919(17) . ? C19 H19 0.9500 . ? C20 C21 1.3952(17) . ? C20 C23 1.5044(17) . ? C21 C22 1.3879(16) . ? C21 H21 0.9500 . ? C22 H22 0.9500 . ? C23 H23A 0.9800 . ? C23 H23B 0.9800 . ? C23 H23C 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 120.58(6) . . ? O2 S1 N9 106.26(6) . . ? O1 S1 N9 105.50(5) . . ? O2 S1 C17 108.39(5) . . ? O1 S1 C17 110.11(5) . . ? N9 S1 C17 104.80(5) . . ? C2 N1 C6 117.61(11) . . ? N1 C2 C3 124.04(12) . . ? N1 C2 H2 118.0 . . ? C3 C2 H2 118.0 . . ? C4 C3 C2 118.08(12) . . ? C4 C3 H3 121.0 . . ? C2 C3 H3 121.0 . . ? C3 C4 C5 119.25(12) . . ? C3 C4 H4 120.4 . . ? C5 C4 H4 120.4 . . ? C4 C5 C6 118.91(12) . . ? C4 C5 H5 120.5 . . ? C6 C5 H5 120.5 . . ? N1 C6 C5 122.10(11) . . ? N1 C6 C7 113.45(10) . . ? C5 C6 C7 124.44(10) . . ? C8 C7 C6 128.52(10) . . ? C8 C7 H7 115.7 . . ? C6 C7 H7 115.7 . . ? C7 C8 F1 120.97(10) . . ? C7 C8 N9 127.53(10) . . ? F1 C8 N9 111.50(9) . . ? C8 N9 C10 118.18(10) . . ? C8 N9 S1 117.17(8) . . ? C10 N9 S1 118.47(7) . . ? N9 C10 C11 110.38(9) . . ? N9 C10 H10A 109.6 . . ? C11 C10 H10A 109.6 . . ? N9 C10 H10B 109.6 . . ? C11 C10 H10B 109.6 . . ? H10A C10 H10B 108.1 . . ? C16 C11 C12 119.03(11) . . ? C16 C11 C10 121.03(11) . . ? C12 C11 C10 119.94(10) . . ? C13 C12 C11 120.45(11) . . ? C13 C12 H12 119.8 . . ? C11 C12 H12 119.8 . . ? C14 C13 C12 120.04(12) . . ? C14 C13 H13 120.0 . . ? C12 C13 H13 120.0 . . ? C15 C14 C13 119.84(12) . . ? C15 C14 H14 120.1 . . ? C13 C14 H14 120.1 . . ? C14 C15 C16 120.28(12) . . ? C14 C15 H15 119.9 . . ? C16 C15 H15 119.9 . . ? C11 C16 C15 120.36(12) . . ? C11 C16 H16 119.8 . . ? C15 C16 H16 119.8 . . ? C18 C17 C22 121.20(10) . . ? C18 C17 S1 119.34(8) . . ? C22 C17 S1 119.32(8) . . ? C19 C18 C17 118.86(10) . . ? C19 C18 H18 120.6 . . ? C17 C18 H18 120.6 . . ? C18 C19 C20 121.27(10) . . ? C18 C19 H19 119.4 . . ? C20 C19 H19 119.4 . . ? C19 C20 C21 118.78(11) . . ? C19 C20 C23 120.35(11) . . ? C21 C20 C23 120.86(11) . . ? C22 C21 C20 121.12(11) . . ? C22 C21 H21 119.4 . . ? C20 C21 H21 119.4 . . ? C21 C22 C17 118.71(10) . . ? C21 C22 H22 120.6 . . ? C17 C22 H22 120.6 . . ? C20 C23 H23A 109.5 . . ? C20 C23 H23B 109.5 . . ? H23A C23 H23B 109.5 . . ? C20 C23 H23C 109.5 . . ? H23A C23 H23C 109.5 . . ? H23B C23 H23C 109.5 . . ? _diffrn_measured_fraction_theta_max 0.995 _diffrn_reflns_theta_full 30.00 _diffrn_measured_fraction_theta_full 0.995 _refine_diff_density_max 0.719 _refine_diff_density_min -0.639 _refine_diff_density_rms 0.237 #===END data_2 _database_code_depnum_ccdc_archive 'CCDC 868336' #TrackingRef 'data12.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C22 H19 F2 N O2 S' _chemical_formula_weight 399.44 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' N N 0.0061 0.0033 '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' F F 0.0171 0.0103 '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 P2(1) loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y+1/2, -z' _cell_length_a 9.0138(8) _cell_length_b 12.0813(10) _cell_length_c 9.5129(9) _cell_angle_alpha 90.00 _cell_angle_beta 109.254(4) _cell_angle_gamma 90.00 _cell_volume 978.00(15) _cell_formula_units_Z 2 _cell_measurement_temperature 150(2) _cell_measurement_reflns_used 9603 _cell_measurement_theta_min 2.39 _cell_measurement_theta_max 29.97 _exptl_crystal_description parallelepiped _exptl_crystal_colour colorless _exptl_crystal_size_max 0.25 _exptl_crystal_size_mid 0.15 _exptl_crystal_size_min 0.10 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.356 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 416 _exptl_absorpt_coefficient_mu 0.201 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.9514 _exptl_absorpt_correction_T_max 0.9801 _exptl_absorpt_process_details 'SADABS (Sheldrick, V2.10)' _exptl_special_details ; 'Blessing, Acta Cryst. (1995) A51, 33-38' ; _diffrn_ambient_temperature 150(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 'Bruker APEX-II CCD' _diffrn_measurement_method '\f and \w scans' _diffrn_detector_area_resol_mean 512x512 _diffrn_standards_number 0 _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 86545 _diffrn_reflns_av_R_equivalents 0.0270 _diffrn_reflns_av_sigmaI/netI 0.0103 _diffrn_reflns_limit_h_min -12 _diffrn_reflns_limit_h_max 12 _diffrn_reflns_limit_k_min -16 _diffrn_reflns_limit_k_max 16 _diffrn_reflns_limit_l_min -13 _diffrn_reflns_limit_l_max 13 _diffrn_reflns_theta_min 2.27 _diffrn_reflns_theta_max 30.00 _reflns_number_total 5702 _reflns_number_gt 5542 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker APEX2' _computing_cell_refinement 'Bruker SAINT' _computing_data_reduction 'Bruker SAINT' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Bruker SHELXTL' _computing_publication_material 'Bruker SHELXTL' _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^)+(0.0531P)^2^+0.0956P] 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 -0.01(4) _refine_ls_number_reflns 5702 _refine_ls_number_parameters 254 _refine_ls_number_restraints 1 _refine_ls_R_factor_all 0.0294 _refine_ls_R_factor_gt 0.0283 _refine_ls_wR_factor_ref 0.0789 _refine_ls_wR_factor_gt 0.0779 _refine_ls_goodness_of_fit_ref 1.084 _refine_ls_restrained_S_all 1.084 _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 S1 S 0.17294(3) 0.25214(2) 0.26877(3) 0.02330(6) Uani 1 1 d . . . F1 F 0.37828(10) 0.03262(6) 0.23921(10) 0.03664(18) Uani 1 1 d . . . F2 F 0.78144(10) 0.58138(8) 0.11387(11) 0.0446(2) Uani 1 1 d . . . O1 O 0.15830(11) 0.28928(8) 0.12167(11) 0.03319(19) Uani 1 1 d . . . O2 O 0.15727(11) 0.32894(8) 0.37818(12) 0.0344(2) Uani 1 1 d . . . C1 C 0.52484(16) 0.38457(11) 0.20383(15) 0.0322(2) Uani 1 1 d . . . H1 H 0.4439 0.3835 0.2472 0.039 Uiso 1 1 calc R . . C2 C 0.59324(17) 0.48462(11) 0.18828(15) 0.0335(3) Uani 1 1 d . . . H2 H 0.5591 0.5521 0.2188 0.040 Uiso 1 1 calc R . . C3 C 0.71320(15) 0.48322(11) 0.12672(15) 0.0323(2) Uani 1 1 d . . . C4 C 0.76177(15) 0.38895(13) 0.07579(18) 0.0391(3) Uani 1 1 d . . . H4 H 0.8424 0.3912 0.0319 0.047 Uiso 1 1 calc R . . C5 C 0.69011(15) 0.28958(12) 0.08981(16) 0.0340(3) Uani 1 1 d . . . H5 H 0.7212 0.2234 0.0533 0.041 Uiso 1 1 calc R . . C6 C 0.57298(13) 0.28503(10) 0.15668(12) 0.0249(2) Uani 1 1 d . . . C7 C 0.50804(13) 0.17556(10) 0.16811(13) 0.0271(2) Uani 1 1 d . . . H7 H 0.5354 0.1191 0.1115 0.033 Uiso 1 1 calc R . . C8 C 0.41680(13) 0.14269(9) 0.24524(13) 0.0249(2) Uani 1 1 d . . . N9 N 0.35567(11) 0.20251(8) 0.33997(10) 0.02284(17) Uani 1 1 d . . . C10 C 0.40053(13) 0.15908(10) 0.49511(13) 0.0264(2) Uani 1 1 d . . . H10A H 0.3794 0.0786 0.4926 0.032 Uiso 1 1 calc R . . H10B H 0.3361 0.1956 0.5482 0.032 Uiso 1 1 calc R . . C11 C 0.57245(13) 0.18007(10) 0.57756(12) 0.02406(19) Uani 1 1 d . . . C12 C 0.62612(15) 0.28787(11) 0.61069(16) 0.0343(3) Uani 1 1 d . . . H12 H 0.5551 0.3481 0.5788 0.041 Uiso 1 1 calc R . . C13 C 0.78325(17) 0.30812(11) 0.69035(19) 0.0398(3) Uani 1 1 d . . . H13 H 0.8196 0.3820 0.7121 0.048 Uiso 1 1 calc R . . C14 C 0.88688(15) 0.22046(12) 0.73798(15) 0.0342(3) Uani 1 1 d . . . H14 H 0.9940 0.2343 0.7935 0.041 Uiso 1 1 calc R . . C15 C 0.83450(14) 0.11259(11) 0.70480(14) 0.0311(2) Uani 1 1 d . . . H15 H 0.9057 0.0525 0.7367 0.037 Uiso 1 1 calc R . . C16 C 0.67668(14) 0.09269(9) 0.62434(12) 0.0259(2) Uani 1 1 d . . . H16 H 0.6406 0.0188 0.6016 0.031 Uiso 1 1 calc R . . C17 C 0.04224(12) 0.14193(9) 0.25472(12) 0.02102(18) Uani 1 1 d . . . C18 C -0.00975(15) 0.11589(11) 0.37343(13) 0.0293(2) Uani 1 1 d . . . H18 H 0.0247 0.1577 0.4630 0.035 Uiso 1 1 calc R . . C19 C -0.11286(16) 0.02772(12) 0.35843(14) 0.0328(2) Uani 1 1 d . . . H19 H -0.1471 0.0085 0.4396 0.039 Uiso 1 1 calc R . . C20 C -0.16689(13) -0.03289(10) 0.22703(13) 0.0262(2) Uani 1 1 d . . . C21 C -0.11434(13) -0.00448(9) 0.10897(13) 0.0257(2) Uani 1 1 d . . . H21 H -0.1512 -0.0449 0.0184 0.031 Uiso 1 1 calc R . . C22 C -0.00903(13) 0.08188(9) 0.12225(12) 0.02334(19) Uani 1 1 d . . . H22 H 0.0276 0.0998 0.0422 0.028 Uiso 1 1 calc R . . C23 C -0.28116(16) -0.12651(12) 0.21144(18) 0.0386(3) Uani 1 1 d . . . H23A H -0.2487 -0.1714 0.3024 0.058 Uiso 1 1 calc R . . H23B H -0.2828 -0.1727 0.1263 0.058 Uiso 1 1 calc R . . H23C H -0.3864 -0.0964 0.1955 0.058 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 0.02090(11) 0.01799(10) 0.02952(12) 0.00189(9) 0.00629(8) -0.00061(9) F1 0.0416(4) 0.0207(3) 0.0514(5) -0.0026(3) 0.0205(4) -0.0046(3) F2 0.0361(4) 0.0442(5) 0.0553(5) 0.0084(4) 0.0176(4) -0.0156(4) O1 0.0290(4) 0.0303(4) 0.0368(4) 0.0141(3) 0.0063(3) -0.0015(3) O2 0.0313(4) 0.0227(4) 0.0478(5) -0.0095(4) 0.0113(4) -0.0015(3) C1 0.0357(6) 0.0304(6) 0.0382(6) -0.0077(5) 0.0225(5) -0.0087(5) C2 0.0397(7) 0.0301(6) 0.0359(6) -0.0064(5) 0.0193(5) -0.0112(5) C3 0.0242(5) 0.0372(6) 0.0345(6) 0.0076(5) 0.0083(5) -0.0077(5) C4 0.0251(5) 0.0448(8) 0.0539(8) 0.0154(6) 0.0219(5) 0.0056(5) C5 0.0265(5) 0.0349(6) 0.0462(7) 0.0091(5) 0.0196(5) 0.0087(5) C6 0.0197(4) 0.0298(5) 0.0253(5) 0.0016(4) 0.0073(4) 0.0002(4) C7 0.0255(5) 0.0268(5) 0.0298(5) -0.0027(4) 0.0100(4) 0.0003(4) C8 0.0228(5) 0.0217(5) 0.0285(5) 0.0001(4) 0.0062(4) -0.0010(4) N9 0.0186(4) 0.0242(4) 0.0247(4) 0.0026(3) 0.0058(3) -0.0020(3) C10 0.0220(5) 0.0307(5) 0.0249(5) 0.0056(4) 0.0055(4) -0.0036(4) C11 0.0223(5) 0.0255(5) 0.0234(4) 0.0007(4) 0.0063(4) -0.0011(4) C12 0.0268(6) 0.0236(5) 0.0454(7) -0.0039(5) 0.0024(5) 0.0026(4) C13 0.0316(6) 0.0265(6) 0.0524(8) -0.0079(5) 0.0017(6) -0.0040(5) C14 0.0236(5) 0.0375(6) 0.0358(6) -0.0043(5) 0.0022(4) -0.0015(4) C15 0.0268(6) 0.0318(6) 0.0314(5) 0.0027(5) 0.0053(4) 0.0056(4) C16 0.0278(5) 0.0220(5) 0.0263(5) 0.0010(4) 0.0067(4) 0.0000(4) C17 0.0172(4) 0.0206(4) 0.0248(4) -0.0001(3) 0.0062(3) -0.0006(3) C18 0.0301(5) 0.0350(6) 0.0249(5) -0.0063(4) 0.0119(4) -0.0081(5) C19 0.0320(6) 0.0411(6) 0.0300(5) -0.0033(5) 0.0163(5) -0.0109(5) C20 0.0202(5) 0.0243(5) 0.0336(6) 0.0001(4) 0.0081(4) -0.0018(4) C21 0.0237(5) 0.0236(5) 0.0291(5) -0.0054(4) 0.0079(4) -0.0007(4) C22 0.0223(5) 0.0244(5) 0.0245(4) -0.0015(4) 0.0093(4) 0.0010(4) C23 0.0312(6) 0.0324(6) 0.0527(8) -0.0016(5) 0.0145(6) -0.0119(5) _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 O1 1.4336(10) . ? S1 O2 1.4356(10) . ? S1 N9 1.6720(10) . ? S1 C17 1.7535(11) . ? F1 C8 1.3708(13) . ? F2 C3 1.3599(14) . ? C1 C2 1.3867(17) . ? C1 C6 1.4014(17) . ? C1 H1 0.9500 . ? C2 C3 1.3892(18) . ? C2 H2 0.9500 . ? C3 C4 1.365(2) . ? C4 C5 1.390(2) . ? C4 H4 0.9500 . ? C5 C6 1.4019(16) . ? C5 H5 0.9500 . ? C6 C7 1.4648(16) . ? C7 C8 1.3306(17) . ? C7 H7 0.9500 . ? C8 N9 1.4019(15) . ? N9 C10 1.4911(14) . ? C10 C11 1.5097(15) . ? C10 H10A 0.9900 . ? C10 H10B 0.9900 . ? C11 C16 1.3854(16) . ? C11 C12 1.3888(17) . ? C12 C13 1.3901(18) . ? C12 H12 0.9500 . ? C13 C14 1.3857(19) . ? C13 H13 0.9500 . ? C14 C15 1.3866(19) . ? C14 H14 0.9500 . ? C15 C16 1.3962(16) . ? C15 H15 0.9500 . ? C16 H16 0.9500 . ? C17 C18 1.3939(15) . ? C17 C22 1.3942(15) . ? C18 C19 1.3897(17) . ? C18 H18 0.9500 . ? C19 C20 1.3907(17) . ? C19 H19 0.9500 . ? C20 C21 1.3980(16) . ? C20 C23 1.5038(16) . ? C21 C22 1.3879(15) . ? C21 H21 0.9500 . ? C22 H22 0.9500 . ? C23 H23A 0.9800 . ? C23 H23B 0.9800 . ? C23 H23C 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 O1 S1 O2 120.39(6) . . ? O1 S1 N9 105.60(5) . . ? O2 S1 N9 104.92(5) . . ? O1 S1 C17 108.66(5) . . ? O2 S1 C17 108.78(5) . . ? N9 S1 C17 107.81(5) . . ? C2 C1 C6 121.22(11) . . ? C2 C1 H1 119.4 . . ? C6 C1 H1 119.4 . . ? C1 C2 C3 118.01(12) . . ? C1 C2 H2 121.0 . . ? C3 C2 H2 121.0 . . ? F2 C3 C4 119.22(11) . . ? F2 C3 C2 117.73(12) . . ? C4 C3 C2 123.03(12) . . ? C3 C4 C5 118.22(11) . . ? C3 C4 H4 120.9 . . ? C5 C4 H4 120.9 . . ? C4 C5 C6 121.37(13) . . ? C4 C5 H5 119.3 . . ? C6 C5 H5 119.3 . . ? C1 C6 C5 118.07(11) . . ? C1 C6 C7 125.28(10) . . ? C5 C6 C7 116.63(11) . . ? C8 C7 C6 130.18(11) . . ? C8 C7 H7 114.9 . . ? C6 C7 H7 114.9 . . ? C7 C8 F1 117.42(10) . . ? C7 C8 N9 130.25(11) . . ? F1 C8 N9 112.28(10) . . ? C8 N9 C10 114.77(9) . . ? C8 N9 S1 117.90(8) . . ? C10 N9 S1 115.88(7) . . ? N9 C10 C11 110.61(9) . . ? N9 C10 H10A 109.5 . . ? C11 C10 H10A 109.5 . . ? N9 C10 H10B 109.5 . . ? C11 C10 H10B 109.5 . . ? H10A C10 H10B 108.1 . . ? C16 C11 C12 119.55(10) . . ? C16 C11 C10 120.66(11) . . ? C12 C11 C10 119.77(11) . . ? C11 C12 C13 120.31(11) . . ? C11 C12 H12 119.8 . . ? C13 C12 H12 119.8 . . ? C14 C13 C12 119.97(12) . . ? C14 C13 H13 120.0 . . ? C12 C13 H13 120.0 . . ? C13 C14 C15 120.11(12) . . ? C13 C14 H14 119.9 . . ? C15 C14 H14 119.9 . . ? C14 C15 C16 119.70(11) . . ? C14 C15 H15 120.1 . . ? C16 C15 H15 120.1 . . ? C11 C16 C15 120.35(11) . . ? C11 C16 H16 119.8 . . ? C15 C16 H16 119.8 . . ? C18 C17 C22 121.00(10) . . ? C18 C17 S1 120.43(8) . . ? C22 C17 S1 118.57(8) . . ? C19 C18 C17 118.81(10) . . ? C19 C18 H18 120.6 . . ? C17 C18 H18 120.6 . . ? C18 C19 C20 121.33(11) . . ? C18 C19 H19 119.3 . . ? C20 C19 H19 119.3 . . ? C19 C20 C21 118.80(10) . . ? C19 C20 C23 120.67(11) . . ? C21 C20 C23 120.52(11) . . ? C22 C21 C20 120.94(10) . . ? C22 C21 H21 119.5 . . ? C20 C21 H21 119.5 . . ? C21 C22 C17 119.10(10) . . ? C21 C22 H22 120.4 . . ? C17 C22 H22 120.4 . . ? C20 C23 H23A 109.5 . . ? C20 C23 H23B 109.5 . . ? H23A C23 H23B 109.5 . . ? C20 C23 H23C 109.5 . . ? H23A C23 H23C 109.5 . . ? H23B C23 H23C 109.5 . . ? _diffrn_measured_fraction_theta_max 0.998 _diffrn_reflns_theta_full 30.00 _diffrn_measured_fraction_theta_full 0.998 _refine_diff_density_max 0.413 _refine_diff_density_min -0.175 _refine_diff_density_rms 0.044 #===END