#------------------------------------------------------------------------------ #$Date: 2016-03-21 18:35:38 +0200 (Mon, 21 Mar 2016) $ #$Revision: 178817 $ #$URL: file:///home/coder/svn-repositories/cod/cif/4/10/71/4107182.cif $ #------------------------------------------------------------------------------ # # This file is available in the Crystallography Open Database (COD), # http://www.crystallography.net/ # # All data on this site have been placed in the public domain by the # contributors. # data_4107182 loop_ _publ_author_name 'Ourida Saidi' 'Jameel Marafie' 'Araminta E. W. Ledger' 'Po Man Liu' 'Mary F. Mahon' 'Gabriele Kociok-K\"ohn' 'Michael K. Whittlesey' 'Christopher G. Frost' _publ_section_title ; Ruthenium-Catalyzed Meta Sulfonation of 2-Phenylpyridines ; _journal_name_full 'Journal of the American Chemical Society' _journal_page_first 19298 _journal_page_last 19301 _journal_paper_doi 10.1021/ja208286b _journal_volume 133 _journal_year 2011 _chemical_formula_moiety 'C17 H12 F N O2 S' _chemical_formula_sum 'C17 H12 F N O2 S' _chemical_formula_weight 313.34 _chemical_name_systematic ; ? ; _space_group_IT_number 14 _symmetry_cell_setting monoclinic _symmetry_space_group_name_Hall '-P 2yab' _symmetry_space_group_name_H-M 'P 1 21/a 1' _atom_sites_solution_hydrogens geom _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _audit_creation_method SHELXL-97 _cell_angle_alpha 90.00 _cell_angle_beta 92.162(2) _cell_angle_gamma 90.00 _cell_formula_units_Z 4 _cell_length_a 11.6399(4) _cell_length_b 6.7536(2) _cell_length_c 17.8463(7) _cell_measurement_reflns_used 12232 _cell_measurement_temperature 150(2) _cell_measurement_theta_max 27.485 _cell_measurement_theta_min 2.910 _cell_volume 1401.92(8) _computing_cell_refinement 'HKL Scalepack (Otwinski & Minor, 1997)' _computing_data_collection 'Collect (Nonius BV, 1997-2000)' _computing_data_reduction ; DENZO-SCALEPACK Z. Otwinowski and W. Minor, " Processing of X-ray Diffraction Data Collected in Oscillation Mode ", Methods in Enzymology, Volume 276: Macromolecular Crystallography, part A, p.307-326, 1997,C.W. Carter, Jr. & R. M. Sweet, Eds., Academic Press. ; _computing_molecular_graphics 'ORTEP3 for Windows - Farrugia, L. J. J. Appl. Crystallogr. 1997, 30, 565' _computing_publication_material ; 'WinGX publication routines, Farrugia, L. J., J. Appl. Crystallogr., 1999, 32, 837-838 ; _computing_structure_refinement ; SHELXL97 -Program for Crystal Structure Analysis (Release 97-2). Sheldrick, G.M., Instit\"ut f\"ur Anorganische Chemie der Universit\"at, Tammanstrasse 4, D-3400 G\"ottingen, Germany, 1998 ; _computing_structure_solution ; SIR97- Altomare A., Burla M.C., Camalli M., Cascarano G.L., Giacovazzo C. , Guagliardi A., Moliterni A.G.G., Polidori G.,Spagna R. (1999) J. Appl. Cryst. 32, 115-119 ; _diffrn_ambient_temperature 150(2) _diffrn_measured_fraction_theta_full 0.992 _diffrn_measured_fraction_theta_max 0.992 _diffrn_measurement_device_type 'Nonius Kappa CCD' _diffrn_measurement_method '158 2.0 degree images with \w scans' _diffrn_radiation_monochromator graphite _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_type MoK\a _diffrn_radiation_wavelength 0.71073 _diffrn_reflns_av_R_equivalents 0.0615 _diffrn_reflns_av_sigmaI/netI 0.0410 _diffrn_reflns_limit_h_max 15 _diffrn_reflns_limit_h_min -15 _diffrn_reflns_limit_k_max 8 _diffrn_reflns_limit_k_min -8 _diffrn_reflns_limit_l_max 22 _diffrn_reflns_limit_l_min -23 _diffrn_reflns_number 15525 _diffrn_reflns_theta_full 27.48 _diffrn_reflns_theta_max 27.48 _diffrn_reflns_theta_min 3.43 _diffrn_standards_decay_% 0 _diffrn_standards_number 0 _exptl_absorpt_coefficient_mu 0.249 _exptl_absorpt_correction_type none _exptl_crystal_colour colourless _exptl_crystal_density_diffrn 1.485 _exptl_crystal_description prism _exptl_crystal_F_000 648 _exptl_crystal_size_max 0.50 _exptl_crystal_size_mid 0.20 _exptl_crystal_size_min 0.13 _refine_diff_density_max 0.246 _refine_diff_density_min -0.506 _refine_diff_density_rms 0.067 _refine_ls_extinction_method none _refine_ls_goodness_of_fit_ref 1.035 _refine_ls_hydrogen_treatment constr _refine_ls_matrix_type full _refine_ls_number_parameters 199 _refine_ls_number_reflns 3195 _refine_ls_number_restraints 0 _refine_ls_restrained_S_all 1.035 _refine_ls_R_factor_all 0.0582 _refine_ls_R_factor_gt 0.0403 _refine_ls_shift/su_max 0.001 _refine_ls_shift/su_mean 0.000 _refine_ls_structure_factor_coef Fsqd _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0509P)^2^+0.3972P] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_gt 0.0928 _refine_ls_wR_factor_ref 0.1012 _reflns_number_gt 2491 _reflns_number_total 3195 _reflns_threshold_expression >2sigma(I) _cod_data_source_file ja208286b_si_004.cif _cod_data_source_block h11cgf2 _cod_database_code 4107182 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, y+1/2, -z' '-x, -y, -z' 'x-1/2, -y-1/2, z' 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 S S 0.65666(3) 0.35108(6) 0.81524(2) 0.02292(13) Uani 1 1 d . O1 O 0.76048(9) 0.46061(18) 0.80412(6) 0.0299(3) Uani 1 1 d . O2 O 0.66313(10) 0.16580(17) 0.85499(6) 0.0294(3) Uani 1 1 d . N N 0.34707(12) -0.1203(2) 0.57041(8) 0.0291(3) Uani 1 1 d . F F 0.33869(9) 0.86076(16) 0.97132(6) 0.0403(3) Uani 1 1 d . C1 C 0.55974(13) 0.5059(2) 0.86151(8) 0.0222(3) Uani 1 1 d . C2 C 0.58806(14) 0.7033(2) 0.87410(9) 0.0252(4) Uani 1 1 d . H2 H 0.6581 0.7554 0.8568 0.030 Uiso 1 1 calc R C3 C 0.51324(15) 0.8236(3) 0.91208(9) 0.0286(4) Uani 1 1 d . H3 H 0.5313 0.9585 0.9219 0.034 Uiso 1 1 calc R C4 C 0.41225(14) 0.7424(3) 0.93514(9) 0.0281(4) Uani 1 1 d . C5 C 0.38175(14) 0.5471(3) 0.92312(9) 0.0296(4) Uani 1 1 d . H5 H 0.3113 0.4964 0.9403 0.036 Uiso 1 1 calc R C6 C 0.45657(14) 0.4274(3) 0.88543(9) 0.0270(4) Uani 1 1 d . H6 H 0.4379 0.2926 0.8759 0.032 Uiso 1 1 calc R C7 C 0.58983(13) 0.3014(2) 0.72653(9) 0.0223(3) Uani 1 1 d . C8 C 0.60828(13) 0.4264(3) 0.66663(9) 0.0243(3) Uani 1 1 d . H8 H 0.6545 0.5416 0.6728 0.029 Uiso 1 1 calc R C9 C 0.55756(14) 0.3792(2) 0.59737(9) 0.0264(4) Uani 1 1 d . H9 H 0.5690 0.4632 0.5556 0.032 Uiso 1 1 calc R C10 C 0.49031(13) 0.2106(2) 0.58851(9) 0.0253(4) Uani 1 1 d . H10 H 0.4571 0.1799 0.5405 0.030 Uiso 1 1 calc R C11 C 0.47039(13) 0.0848(2) 0.64909(9) 0.0224(3) Uani 1 1 d . C12 C 0.39903(13) -0.0978(2) 0.63874(9) 0.0234(3) Uani 1 1 d . C13 C 0.28118(15) -0.2814(3) 0.55918(10) 0.0333(4) Uani 1 1 d . H13 H 0.2447 -0.2987 0.5111 0.040 Uiso 1 1 calc R C14 C 0.26310(14) -0.4232(3) 0.61286(10) 0.0330(4) Uani 1 1 d . H14 H 0.2153 -0.5344 0.6021 0.040 Uiso 1 1 calc R C15 C 0.31659(15) -0.3993(3) 0.68294(10) 0.0319(4) Uani 1 1 d . H15 H 0.3060 -0.4938 0.7215 0.038 Uiso 1 1 calc R C16 C 0.38566(14) -0.2354(2) 0.69570(9) 0.0273(4) Uani 1 1 d . H16 H 0.4238 -0.2169 0.7432 0.033 Uiso 1 1 calc R C17 C 0.52147(13) 0.1333(2) 0.71882(9) 0.0229(3) Uani 1 1 d . H17 H 0.5094 0.0513 0.7610 0.027 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 S 0.0196(2) 0.0250(2) 0.0239(2) 0.00055(16) -0.00166(14) -0.00184(15) O1 0.0200(6) 0.0374(7) 0.0323(6) -0.0022(5) 0.0009(5) -0.0064(5) O2 0.0314(7) 0.0271(6) 0.0292(6) 0.0032(5) -0.0058(5) 0.0019(5) N 0.0236(7) 0.0369(8) 0.0267(7) -0.0072(6) 0.0001(6) -0.0030(6) F 0.0358(6) 0.0497(7) 0.0357(6) -0.0143(5) 0.0049(5) 0.0070(5) C1 0.0209(8) 0.0254(8) 0.0203(8) 0.0016(6) -0.0018(6) -0.0021(6) C2 0.0249(8) 0.0270(8) 0.0234(8) 0.0016(7) -0.0015(6) -0.0068(7) C3 0.0347(10) 0.0264(8) 0.0244(8) -0.0024(7) -0.0018(7) -0.0031(7) C4 0.0279(9) 0.0367(10) 0.0196(8) -0.0047(7) -0.0010(6) 0.0050(7) C5 0.0227(8) 0.0390(10) 0.0272(9) -0.0009(8) 0.0020(7) -0.0051(7) C6 0.0267(9) 0.0276(9) 0.0266(8) 0.0001(7) -0.0011(7) -0.0061(7) C7 0.0177(7) 0.0257(8) 0.0237(8) -0.0005(7) 0.0015(6) 0.0009(6) C8 0.0195(8) 0.0250(8) 0.0285(9) 0.0004(7) 0.0025(6) -0.0001(6) C9 0.0246(8) 0.0305(9) 0.0243(8) 0.0044(7) 0.0031(6) 0.0024(7) C10 0.0198(8) 0.0322(9) 0.0237(8) -0.0006(7) -0.0012(6) 0.0034(7) C11 0.0164(7) 0.0255(8) 0.0252(8) -0.0023(7) 0.0014(6) 0.0026(6) C12 0.0172(8) 0.0265(8) 0.0265(8) -0.0047(7) 0.0016(6) 0.0022(6) C13 0.0238(9) 0.0441(11) 0.0320(9) -0.0125(9) 0.0006(7) -0.0040(8) C14 0.0215(9) 0.0331(9) 0.0446(11) -0.0125(9) 0.0033(7) -0.0042(7) C15 0.0281(9) 0.0273(9) 0.0405(10) -0.0021(8) 0.0020(7) -0.0003(7) C16 0.0236(8) 0.0275(9) 0.0305(9) -0.0036(7) -0.0025(7) 0.0010(7) C17 0.0214(8) 0.0246(8) 0.0226(8) 0.0008(7) 0.0017(6) 0.0005(6) 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' loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle O1 S O2 119.14(7) O1 S C1 108.38(7) O2 S C1 107.87(7) O1 S C7 108.52(7) O2 S C7 106.81(7) C1 S C7 105.29(7) C13 N C12 117.43(15) C2 C1 C6 121.13(15) C2 C1 S 119.46(12) C6 C1 S 119.41(12) C3 C2 C1 119.45(15) C3 C2 H2 120.3 C1 C2 H2 120.3 C4 C3 C2 118.22(16) C4 C3 H3 120.9 C2 C3 H3 120.9 F C4 C3 118.11(16) F C4 C5 118.35(15) C3 C4 C5 123.54(16) C4 C5 C6 118.13(15) C4 C5 H5 120.9 C6 C5 H5 120.9 C5 C6 C1 119.52(16) C5 C6 H6 120.2 C1 C6 H6 120.2 C8 C7 C17 121.74(15) C8 C7 S 119.94(12) C17 C7 S 118.30(12) C7 C8 C9 118.33(15) C7 C8 H8 120.8 C9 C8 H8 120.8 C8 C9 C10 120.64(15) C8 C9 H9 119.7 C10 C9 H9 119.7 C9 C10 C11 121.25(15) C9 C10 H10 119.4 C11 C10 H10 119.4 C17 C11 C10 117.88(15) C17 C11 C12 121.29(14) C10 C11 C12 120.82(14) N C12 C16 121.77(15) N C12 C11 115.66(14) C16 C12 C11 122.57(14) N C13 C14 124.18(16) N C13 H13 117.9 C14 C13 H13 117.9 C13 C14 C15 118.17(17) C13 C14 H14 120.9 C15 C14 H14 120.9 C16 C15 C14 118.74(17) C16 C15 H15 120.6 C14 C15 H15 120.6 C15 C16 C12 119.70(16) C15 C16 H16 120.1 C12 C16 H16 120.1 C7 C17 C11 120.16(15) C7 C17 H17 119.9 C11 C17 H17 119.9 loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance S O1 1.4370(12) S O2 1.4390(12) S C1 1.7657(16) S C7 1.7695(16) N C13 1.342(2) N C12 1.349(2) F C4 1.3531(19) C1 C2 1.390(2) C1 C6 1.394(2) C2 C3 1.386(2) C2 H2 0.9500 C3 C4 1.374(2) C3 H3 0.9500 C4 C5 1.381(3) C5 C6 1.381(2) C5 H5 0.9500 C6 H6 0.9500 C7 C8 1.385(2) C7 C17 1.390(2) C8 C9 1.387(2) C8 H8 0.9500 C9 C10 1.388(2) C9 H9 0.9500 C10 C11 1.401(2) C10 H10 0.9500 C11 C17 1.398(2) C11 C12 1.494(2) C12 C16 1.391(2) C13 C14 1.376(3) C13 H13 0.9500 C14 C15 1.385(3) C14 H14 0.9500 C15 C16 1.382(2) C15 H15 0.9500 C16 H16 0.9500 C17 H17 0.9500