# Electronic Supplementary Material (ESI) for Chemical Communications # This journal is © The Royal Society of Chemistry 2013 ####################################################################### # # Cambridge Crystallographic Data Centre # CCDC # ####################################################################### # # This CIF contains data from an original supplementary publication # deposited with the CCDC, and may include chemical, crystal, # experimental, refinement, atomic coordinates, # anisotropic displacement parameters and molecular geometry data, # as required by the journal to which it was submitted. # # This CIF is provided on the understanding that it is used for bona # fide research purposes only. It may contain copyright material # of the CCDC or of third parties, and may not be copied or further # disseminated in any form, whether machine-readable or not, # except for the purpose of generating routine backup copies # on your local computer system. # # For further information on the CCDC, data deposition and # data retrieval see: # www.ccdc.cam.ac.uk # # Bona fide researchers may freely download Mercury and enCIFer # from this site to visualise CIF-encoded structures and # to carry out CIF format checking respectively. # ####################################################################### data_ram_a _database_code_depnum_ccdc_archive 'CCDC 903580' #TrackingRef 'RAM_A.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C24 H19 F N2 O2 S' _chemical_formula_weight 418.48 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 Triclinic _symmetry_space_group_name_H-M 'P-1 ' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 8.4548(9) _cell_length_b 11.3819(12) _cell_length_c 11.7256(12) _cell_angle_alpha 106.632(2) _cell_angle_beta 107.674(3) _cell_angle_gamma 91.787(2) _cell_volume 1021.48(19) _cell_formula_units_Z 2 _cell_measurement_temperature 298(2) _cell_measurement_reflns_used 5698 _cell_measurement_theta_min 2.55 _cell_measurement_theta_max 27.66 _exptl_crystal_description PLATE _exptl_crystal_colour WHITE _exptl_crystal_size_max 0.49 _exptl_crystal_size_mid 0.21 _exptl_crystal_size_min 0.12 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.361 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 436 _exptl_absorpt_coefficient_mu 0.192 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.953 _exptl_absorpt_correction_T_max 0.977 _exptl_absorpt_process_details 'SADABS; BRUKER, 2008' _exptl_special_details ; ? ; _diffrn_ambient_temperature 298(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 DUO' _diffrn_measurement_method '\ f and \ w scans' _diffrn_detector_area_resol_mean ? _diffrn_reflns_number 18280 _diffrn_reflns_av_R_equivalents 0.0283 _diffrn_reflns_av_sigmaI/netI 0.0267 _diffrn_reflns_limit_h_min -9 _diffrn_reflns_limit_h_max 11 _diffrn_reflns_limit_k_min -15 _diffrn_reflns_limit_k_max 15 _diffrn_reflns_limit_l_min -15 _diffrn_reflns_limit_l_max 15 _diffrn_reflns_theta_min 1.88 _diffrn_reflns_theta_max 28.00 _reflns_number_total 4932 _reflns_number_gt 3687 _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, 2008)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 2008)' _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^)+(0.0432P)^2^+0.2763P] 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 SHELXL _refine_ls_extinction_coef 0.0041(12) _refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^ _refine_ls_number_reflns 4932 _refine_ls_number_parameters 273 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0581 _refine_ls_R_factor_gt 0.0393 _refine_ls_wR_factor_ref 0.1072 _refine_ls_wR_factor_gt 0.0952 _refine_ls_goodness_of_fit_ref 1.036 _refine_ls_restrained_S_all 1.036 _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 O1 O 0.29492(15) 0.03212(10) 0.28603(11) 0.0510(3) Uani 1 1 d . . . N2 N 0.36320(16) 0.26074(12) 0.35655(12) 0.0418(3) Uani 1 1 d . . . S1 S 0.29968(5) 0.12953(4) 0.23336(4) 0.04224(12) Uani 1 1 d . . . C17 C 0.2280(3) -0.0761(2) 0.5829(2) 0.0734(6) Uani 1 1 d . . . H17A H 0.3106 -0.0624 0.6605 0.088 Uiso 1 1 calc R . . H17B H 0.1435 -0.1423 0.5529 0.088 Uiso 1 1 calc R . . C16 C 0.2308(2) -0.00303(16) 0.51685(18) 0.0536(4) Uani 1 1 d . . . H16 H 0.1461 -0.0198 0.4398 0.064 Uiso 1 1 calc R . . C15 C 0.3594(2) 0.10629(15) 0.55449(16) 0.0457(4) Uani 1 1 d . . . H15A H 0.4263 0.1228 0.6421 0.055 Uiso 1 1 calc R . . H15B H 0.4334 0.0863 0.5046 0.055 Uiso 1 1 calc R . . N1 N 0.28766(17) 0.21797(12) 0.53845(12) 0.0427(3) Uani 1 1 d . . . C14 C 0.29743(19) 0.28159(14) 0.45725(14) 0.0398(3) Uani 1 1 d . . . C18 C 0.09610(19) 0.14501(14) 0.14831(14) 0.0385(3) Uani 1 1 d . . . C19 C 0.0662(2) 0.17781(15) 0.03975(15) 0.0459(4) Uani 1 1 d . . . H19 H 0.1533 0.1896 0.0096 0.055 Uiso 1 1 calc R . . C20 C -0.0947(2) 0.19285(16) -0.02344(15) 0.0481(4) Uani 1 1 d . . . H20 H -0.1154 0.2144 -0.0969 0.058 Uiso 1 1 calc R . . C21 C -0.2259(2) 0.17652(15) 0.02017(15) 0.0451(4) Uani 1 1 d . . . C24 C -0.4008(2) 0.1946(2) -0.04830(19) 0.0659(5) Uani 1 1 d . . . H24A H -0.4181 0.2788 -0.0150 0.099 Uiso 1 1 calc R . . H24B H -0.4801 0.1403 -0.0372 0.099 Uiso 1 1 calc R . . H24C H -0.4157 0.1761 -0.1364 0.099 Uiso 1 1 calc R . . C3 C 0.1592(3) 0.3766(2) 0.8138(2) 0.0701(6) Uani 1 1 d . . . H3 H 0.1427 0.3670 0.8857 0.084 Uiso 1 1 calc R . . C2 C 0.2059(2) 0.27942(19) 0.73408(18) 0.0586(5) Uani 1 1 d . . . H2 H 0.2201 0.2045 0.7504 0.070 Uiso 1 1 calc R . . C1 C 0.2307(2) 0.29860(15) 0.62864(15) 0.0456(4) Uani 1 1 d . . . C6 C 0.2076(2) 0.41129(15) 0.60161(16) 0.0457(4) Uani 1 1 d . . . C7 C 0.2514(2) 0.39738(14) 0.49005(15) 0.0431(4) Uani 1 1 d . . . C8 C 0.2856(2) 0.45975(15) 0.40760(15) 0.0457(4) Uani 1 1 d . . . C9 C 0.2686(2) 0.57755(17) 0.39699(19) 0.0577(5) Uani 1 1 d . . . H9 H 0.2277 0.6358 0.4508 0.069 Uiso 1 1 calc R . . C10 C 0.3144(3) 0.60407(18) 0.3043(2) 0.0656(6) Uani 1 1 d . . . F1 F 0.29540(19) 0.71863(12) 0.29067(14) 0.0935(5) Uani 1 1 d . . . C11 C 0.3783(3) 0.5234(2) 0.2234(2) 0.0689(6) Uani 1 1 d . . . H11 H 0.4065 0.5467 0.1616 0.083 Uiso 1 1 calc R . . C12 C 0.4002(2) 0.40644(18) 0.23476(18) 0.0588(5) Uani 1 1 d . . . H12 H 0.4453 0.3504 0.1822 0.071 Uiso 1 1 calc R . . C13 C 0.3531(2) 0.37611(15) 0.32647(15) 0.0450(4) Uani 1 1 d . . . C22 C -0.1928(2) 0.14354(18) 0.12916(17) 0.0527(4) Uani 1 1 d . . . H22 H -0.2798 0.1323 0.1597 0.063 Uiso 1 1 calc R . . C23 C -0.0334(2) 0.12704(17) 0.19326(16) 0.0495(4) Uani 1 1 d . . . H23 H -0.0130 0.1041 0.2659 0.059 Uiso 1 1 calc R . . O2 O 0.40667(15) 0.13162(12) 0.16056(12) 0.0575(3) Uani 1 1 d . . . C5 C 0.1592(2) 0.50683(17) 0.68418(19) 0.0585(5) Uani 1 1 d . . . H5 H 0.1427 0.5818 0.6684 0.070 Uiso 1 1 calc R . . C4 C 0.1364(3) 0.4882(2) 0.7891(2) 0.0704(6) Uani 1 1 d . . . H4 H 0.1051 0.5516 0.8447 0.085 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 O1 0.0572(7) 0.0432(6) 0.0490(7) 0.0131(5) 0.0128(6) 0.0142(5) N2 0.0393(7) 0.0421(7) 0.0387(7) 0.0099(5) 0.0077(6) 0.0031(6) S1 0.0377(2) 0.0454(2) 0.0405(2) 0.00907(16) 0.01198(17) 0.00952(16) C17 0.0761(15) 0.0707(13) 0.0922(16) 0.0418(12) 0.0377(13) 0.0159(11) C16 0.0554(11) 0.0493(10) 0.0569(10) 0.0201(8) 0.0154(9) 0.0123(8) C15 0.0440(9) 0.0474(9) 0.0469(9) 0.0201(7) 0.0103(7) 0.0152(7) N1 0.0455(8) 0.0413(7) 0.0423(7) 0.0145(6) 0.0138(6) 0.0125(6) C14 0.0354(8) 0.0415(8) 0.0372(8) 0.0111(6) 0.0051(6) 0.0062(6) C18 0.0362(8) 0.0398(8) 0.0342(7) 0.0062(6) 0.0091(6) 0.0041(6) C19 0.0459(9) 0.0516(9) 0.0398(8) 0.0125(7) 0.0154(7) 0.0020(7) C20 0.0514(10) 0.0541(10) 0.0379(8) 0.0177(7) 0.0103(7) 0.0065(8) C21 0.0424(9) 0.0461(9) 0.0402(8) 0.0089(7) 0.0081(7) 0.0088(7) C24 0.0511(11) 0.0864(14) 0.0592(12) 0.0270(11) 0.0111(9) 0.0232(10) C3 0.0738(14) 0.0799(15) 0.0564(12) 0.0100(10) 0.0320(11) 0.0073(11) C2 0.0602(12) 0.0634(11) 0.0541(11) 0.0173(9) 0.0220(9) 0.0089(9) C1 0.0397(9) 0.0469(9) 0.0441(9) 0.0084(7) 0.0105(7) 0.0063(7) C6 0.0360(8) 0.0442(8) 0.0476(9) 0.0074(7) 0.0069(7) 0.0069(7) C7 0.0382(8) 0.0392(8) 0.0439(8) 0.0109(7) 0.0038(7) 0.0080(6) C8 0.0366(8) 0.0430(8) 0.0467(9) 0.0147(7) -0.0017(7) 0.0008(7) C9 0.0493(10) 0.0445(9) 0.0668(12) 0.0193(8) -0.0004(9) 0.0017(8) C10 0.0584(12) 0.0520(11) 0.0740(13) 0.0332(10) -0.0070(10) -0.0111(9) F1 0.1011(10) 0.0623(8) 0.1133(11) 0.0526(8) 0.0071(9) -0.0036(7) C11 0.0677(13) 0.0716(13) 0.0621(12) 0.0330(11) 0.0050(10) -0.0192(11) C12 0.0557(11) 0.0610(11) 0.0525(10) 0.0174(9) 0.0097(9) -0.0108(9) C13 0.0366(8) 0.0457(9) 0.0430(8) 0.0141(7) 0.0000(7) -0.0046(7) C22 0.0397(9) 0.0736(12) 0.0504(10) 0.0227(9) 0.0189(8) 0.0108(8) C23 0.0434(9) 0.0694(11) 0.0417(9) 0.0244(8) 0.0153(7) 0.0112(8) O2 0.0456(7) 0.0728(8) 0.0560(7) 0.0134(6) 0.0247(6) 0.0134(6) C5 0.0511(11) 0.0491(10) 0.0646(12) 0.0042(8) 0.0161(9) 0.0114(8) C4 0.0654(13) 0.0696(13) 0.0655(13) -0.0047(10) 0.0301(11) 0.0098(10) _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 S1 1.4201(12) . ? N2 C14 1.416(2) . ? N2 C13 1.453(2) . ? N2 S1 1.6880(13) . ? S1 O2 1.4236(12) . ? S1 C18 1.7508(16) . ? C17 C16 1.293(3) . ? C17 H17A 0.9300 . ? C17 H17B 0.9300 . ? C16 C15 1.495(2) . ? C16 H16 0.9300 . ? C15 N1 1.4612(19) . ? C15 H15A 0.9700 . ? C15 H15B 0.9700 . ? N1 C14 1.370(2) . ? N1 C1 1.405(2) . ? C14 C7 1.367(2) . ? C18 C19 1.381(2) . ? C18 C23 1.384(2) . ? C19 C20 1.380(2) . ? C19 H19 0.9300 . ? C20 C21 1.383(2) . ? C20 H20 0.9300 . ? C21 C22 1.384(2) . ? C21 C24 1.505(2) . ? C24 H24A 0.9600 . ? C24 H24B 0.9600 . ? C24 H24C 0.9600 . ? C3 C2 1.383(3) . ? C3 C4 1.388(3) . ? C3 H3 0.9300 . ? C2 C1 1.389(2) . ? C2 H2 0.9300 . ? C1 C6 1.412(2) . ? C6 C5 1.397(2) . ? C6 C7 1.433(2) . ? C7 C8 1.439(2) . ? C8 C9 1.389(2) . ? C8 C13 1.408(2) . ? C9 C10 1.364(3) . ? C9 H9 0.9300 . ? C10 F1 1.367(2) . ? C10 C11 1.370(3) . ? C11 C12 1.388(3) . ? C11 H11 0.9300 . ? C12 C13 1.378(2) . ? C12 H12 0.9300 . ? C22 C23 1.378(2) . ? C22 H22 0.9300 . ? C23 H23 0.9300 . ? C5 C4 1.373(3) . ? C5 H5 0.9300 . ? C4 H4 0.9300 . ? 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 C14 N2 C13 103.57(12) . . ? C14 N2 S1 121.01(10) . . ? C13 N2 S1 116.41(10) . . ? O1 S1 O2 120.09(8) . . ? O1 S1 N2 105.82(7) . . ? O2 S1 N2 105.86(7) . . ? O1 S1 C18 109.70(7) . . ? O2 S1 C18 109.40(7) . . ? N2 S1 C18 104.78(7) . . ? C16 C17 H17A 120.0 . . ? C16 C17 H17B 120.0 . . ? H17A C17 H17B 120.0 . . ? C17 C16 C15 125.14(19) . . ? C17 C16 H16 117.4 . . ? C15 C16 H16 117.4 . . ? N1 C15 C16 113.44(14) . . ? N1 C15 H15A 108.9 . . ? C16 C15 H15A 108.9 . . ? N1 C15 H15B 108.9 . . ? C16 C15 H15B 108.9 . . ? H15A C15 H15B 107.7 . . ? C14 N1 C1 105.32(13) . . ? C14 N1 C15 129.55(13) . . ? C1 N1 C15 123.34(13) . . ? C7 C14 N1 112.57(14) . . ? C7 C14 N2 112.53(14) . . ? N1 C14 N2 134.37(14) . . ? C19 C18 C23 120.59(15) . . ? C19 C18 S1 120.34(12) . . ? C23 C18 S1 119.05(12) . . ? C20 C19 C18 119.13(15) . . ? C20 C19 H19 120.4 . . ? C18 C19 H19 120.4 . . ? C19 C20 C21 121.38(15) . . ? C19 C20 H20 119.3 . . ? C21 C20 H20 119.3 . . ? C20 C21 C22 118.41(15) . . ? C20 C21 C24 121.13(16) . . ? C22 C21 C24 120.46(16) . . ? C21 C24 H24A 109.5 . . ? C21 C24 H24B 109.5 . . ? H24A C24 H24B 109.5 . . ? C21 C24 H24C 109.5 . . ? H24A C24 H24C 109.5 . . ? H24B C24 H24C 109.5 . . ? C2 C3 C4 121.53(19) . . ? C2 C3 H3 119.2 . . ? C4 C3 H3 119.2 . . ? C3 C2 C1 117.14(19) . . ? C3 C2 H2 121.4 . . ? C1 C2 H2 121.4 . . ? C2 C1 N1 127.95(16) . . ? C2 C1 C6 122.18(16) . . ? N1 C1 C6 109.80(14) . . ? C5 C6 C1 118.84(17) . . ? C5 C6 C7 135.38(17) . . ? C1 C6 C7 105.69(14) . . ? C14 C7 C6 106.61(14) . . ? C14 C7 C8 107.35(15) . . ? C6 C7 C8 145.42(15) . . ? C9 C8 C13 119.28(17) . . ? C9 C8 C7 133.90(17) . . ? C13 C8 C7 106.80(14) . . ? C10 C9 C8 117.2(2) . . ? C10 C9 H9 121.4 . . ? C8 C9 H9 121.4 . . ? C9 C10 F1 118.0(2) . . ? C9 C10 C11 124.37(18) . . ? F1 C10 C11 117.6(2) . . ? C10 C11 C12 119.28(19) . . ? C10 C11 H11 120.4 . . ? C12 C11 H11 120.4 . . ? C13 C12 C11 117.8(2) . . ? C13 C12 H12 121.1 . . ? C11 C12 H12 121.1 . . ? C12 C13 C8 122.07(17) . . ? C12 C13 N2 128.17(17) . . ? C8 C13 N2 109.76(14) . . ? C23 C22 C21 121.22(16) . . ? C23 C22 H22 119.4 . . ? C21 C22 H22 119.4 . . ? C22 C23 C18 119.26(15) . . ? C22 C23 H23 120.4 . . ? C18 C23 H23 120.4 . . ? C4 C5 C6 118.92(19) . . ? C4 C5 H5 120.6 . . ? C6 C5 H5 120.5 . . ? C5 C4 C3 121.39(18) . . ? C5 C4 H4 119.3 . . ? C3 C4 H4 119.3 . . ? _diffrn_measured_fraction_theta_max 1.000 _diffrn_reflns_theta_full 28.00 _diffrn_measured_fraction_theta_full 1.000 _refine_diff_density_max 0.226 _refine_diff_density_min -0.348 _refine_diff_density_rms 0.036