# Electronic Supplementary Material (ESI) for Organic & Biomolecular Chemistry # This journal is © The Royal Society of Chemistry 2012 data_global _journal_name_full Org.Biomol.Chem. _journal_coden_cambridge 0177 _journal_year ? _journal_volume ? _journal_page_first ? _publ_contact_author_name 'Roman Dembinski' _publ_contact_author_email dembinsk@oakland.edu loop_ _publ_author_name Y.Li K.A.Wheeler R.Dembinski #===END # Attachment '- DEMB18_pub.CIF' data_demb18 _database_code_depnum_ccdc_archive 'CCDC 826570' #TrackingRef '- DEMB18_pub.CIF' _audit_creation_method SHELXL-97 _chemical_name_systematic ; (Z)-((1-(4-bromophenyl)-4-(4-(tert-butyl)phenyl)but-1-en-3-yn-1-yl)oxy)(tert-butyl)dimethylsilane ; _chemical_name_common ; (Z)-((1-(4-bromophenyl)-4-(4-(tert-butyl)phenyl)but-1-en-3-yn- 1-yl)oxy)(tert-but ; _chemical_melting_point ? _chemical_formula_moiety 'C26 H33 Br O Si' _chemical_formula_sum 'C26 H33 Br O Si' _chemical_formula_weight 469.52 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0181 0.0091 '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 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Si Si 0.2541 0.3302 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Br Br -0.6763 1.2805 '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' _symmetry_space_group_name_Hall '-P 1' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 7.0214(2) _cell_length_b 12.5519(5) _cell_length_c 14.2927(5) _cell_angle_alpha 93.591(2) _cell_angle_beta 92.240(2) _cell_angle_gamma 103.988(2) _cell_volume 1217.98(7) _cell_formula_units_Z 2 _cell_measurement_temperature 173(2) _cell_measurement_reflns_used 8178 _cell_measurement_theta_min 3.112 _cell_measurement_theta_max 71.035 _exptl_crystal_description 'transparent prism' _exptl_crystal_colour colorless _exptl_crystal_size_max 0.43 _exptl_crystal_size_mid 0.31 _exptl_crystal_size_min 0.26 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.280 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 492 _exptl_absorpt_coefficient_mu 2.863 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.3724 _exptl_absorpt_correction_T_max 0.5232 _exptl_absorpt_process_details 'SADABS (Bruker, 2010)' _exptl_special_details ; ? ; _diffrn_ambient_temperature 173(2) _diffrn_radiation_wavelength 1.54178 _diffrn_radiation_type CuK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Bruker APEXII CCD' _diffrn_measurement_method 'phi and omega scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count . _diffrn_standards_interval_time . _diffrn_standards_decay_% ? _diffrn_reflns_number 24258 _diffrn_reflns_av_R_equivalents 0.0423 _diffrn_reflns_av_sigmaI/netI 0.0286 _diffrn_reflns_limit_h_min -8 _diffrn_reflns_limit_h_max 8 _diffrn_reflns_limit_k_min -12 _diffrn_reflns_limit_k_max 14 _diffrn_reflns_limit_l_min -17 _diffrn_reflns_limit_l_max 17 _diffrn_reflns_theta_min 3.10 _diffrn_reflns_theta_max 68.23 _reflns_number_total 4343 _reflns_number_gt 4051 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'APEX2 (Bruker, 2010)' _computing_cell_refinement APEX2 _computing_data_reduction ; SAINT (Bruker, 2008) and XPREP (Bruker, 2008) ; _computing_structure_solution 'SHELXS-97 (Sheldrick, 2008)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 2008)' _computing_molecular_graphics 'XSEED (Barbour, 2001)' _computing_publication_material 'XSEED (Barbour, 2001)' _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. All non-hydrogen atoms were located in a single Fourier diff map and refined with anisotropic displacement parameters. H atoms were placed in calculated positions with Ueq = 1.2xUiso of the corresponding attached atom [Ueq = 1.5xUiso for methyl gorups]. residula electron density is located near (0.85 ang) the Br atom. ; _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^)+(0.0618P)^2^+0.4955P] 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 4343 _refine_ls_number_parameters 270 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0382 _refine_ls_R_factor_gt 0.0352 _refine_ls_wR_factor_ref 0.0967 _refine_ls_wR_factor_gt 0.0899 _refine_ls_goodness_of_fit_ref 1.112 _refine_ls_restrained_S_all 1.112 _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 Br1 Br 0.18259(3) 0.350715(19) 0.581085(15) 0.02622(11) Uani 1 1 d . . . Si1 Si 1.01474(8) 0.25426(5) 0.24184(4) 0.01821(14) Uani 1 1 d . . . O1 O 0.9449(2) 0.22999(12) 0.35075(10) 0.0198(3) Uani 1 1 d . . . C2 C 0.7937(3) 0.15311(17) 0.38181(14) 0.0192(4) Uani 1 1 d . . . C3 C 0.7887(3) 0.04499(19) 0.37496(15) 0.0238(4) Uani 1 1 d . . . H3 H 0.6807 -0.0037 0.4001 0.029 Uiso 1 1 calc R . . C4 C 0.9328(3) -0.00176(18) 0.33293(15) 0.0235(4) Uani 1 1 d . . . C5 C 1.0537(3) -0.04401(18) 0.29857(15) 0.0234(4) Uani 1 1 d . . . C6 C 0.6439(3) 0.19858(17) 0.42881(14) 0.0193(4) Uani 1 1 d . . . C7 C 0.6905(3) 0.30936(18) 0.46291(14) 0.0206(4) Uani 1 1 d . . . H7 H 0.8178 0.3543 0.4550 0.025 Uiso 1 1 calc R . . C8 C 0.5545(3) 0.35455(18) 0.50797(14) 0.0214(4) Uani 1 1 d . . . H8 H 0.5878 0.4297 0.5313 0.026 Uiso 1 1 calc R . . C9 C 0.3685(3) 0.28829(18) 0.51860(14) 0.0196(4) Uani 1 1 d . . . C10 C 0.3161(3) 0.17915(18) 0.48456(14) 0.0211(4) Uani 1 1 d . . . H10 H 0.1873 0.1354 0.4915 0.025 Uiso 1 1 calc R . . C11 C 0.4543(3) 0.13423(18) 0.44005(14) 0.0207(4) Uani 1 1 d . . . H11 H 0.4198 0.0590 0.4170 0.025 Uiso 1 1 calc R . . C12 C 1.1949(3) -0.09125(18) 0.25216(15) 0.0216(4) Uani 1 1 d . . . C13 C 1.2823(3) -0.16651(19) 0.29356(15) 0.0245(5) Uani 1 1 d . . . H13 H 1.2519 -0.1859 0.3554 0.029 Uiso 1 1 calc R . . C14 C 1.4130(3) -0.21334(18) 0.24563(15) 0.0235(4) Uani 1 1 d . . . H14 H 1.4711 -0.2642 0.2755 0.028 Uiso 1 1 calc R . . C15 C 1.4619(3) -0.18769(18) 0.15412(15) 0.0215(4) Uani 1 1 d . . . C16 C 1.3754(3) -0.11070(19) 0.11400(15) 0.0235(4) Uani 1 1 d . . . H16 H 1.4065 -0.0908 0.0524 0.028 Uiso 1 1 calc R . . C17 C 1.2466(3) -0.06292(18) 0.16132(15) 0.0234(4) Uani 1 1 d . . . H17 H 1.1920 -0.0102 0.1323 0.028 Uiso 1 1 calc R . . C18 C 1.5943(3) -0.24383(19) 0.09678(15) 0.0237(4) Uani 1 1 d . . . C19 C 1.7526(3) -0.1575(2) 0.05343(19) 0.0333(5) Uani 1 1 d . . . H19A H 1.6899 -0.1174 0.0098 0.050 Uiso 1 1 calc R . . H19B H 1.8403 -0.1942 0.0194 0.050 Uiso 1 1 calc R . . H19C H 1.8287 -0.1058 0.1033 0.050 Uiso 1 1 calc R . . C20 C 1.4670(4) -0.3192(2) 0.01714(17) 0.0315(5) Uani 1 1 d . . . H20A H 1.4059 -0.2749 -0.0232 0.047 Uiso 1 1 calc R . . H20B H 1.3643 -0.3744 0.0440 0.047 Uiso 1 1 calc R . . H20C H 1.5496 -0.3562 -0.0201 0.047 Uiso 1 1 calc R . . C21 C 1.6975(4) -0.3131(2) 0.15580(18) 0.0390(6) Uani 1 1 d . . . H21A H 1.7825 -0.3459 0.1163 0.059 Uiso 1 1 calc R . . H21B H 1.5989 -0.3716 0.1814 0.059 Uiso 1 1 calc R . . H21C H 1.7771 -0.2661 0.2075 0.059 Uiso 1 1 calc R . . C22 C 0.8372(3) 0.15862(19) 0.15620(16) 0.0264(5) Uani 1 1 d . . . H22A H 0.8459 0.0828 0.1638 0.040 Uiso 1 1 calc R . . H22B H 0.8689 0.1776 0.0922 0.040 Uiso 1 1 calc R . . H22C H 0.7036 0.1650 0.1675 0.040 Uiso 1 1 calc R . . C23 C 1.2688(3) 0.23720(19) 0.23472(15) 0.0251(5) Uani 1 1 d . . . H23A H 1.3548 0.2867 0.2831 0.038 Uiso 1 1 calc R . . H23B H 1.3159 0.2551 0.1726 0.038 Uiso 1 1 calc R . . H23C H 1.2700 0.1608 0.2447 0.038 Uiso 1 1 calc R . . C24 C 1.0115(3) 0.40186(18) 0.22649(15) 0.0232(4) Uani 1 1 d . . . C25 C 1.0886(4) 0.4350(2) 0.13042(18) 0.0355(6) Uani 1 1 d . . . H25A H 1.0755 0.5094 0.1205 0.053 Uiso 1 1 calc R . . H25B H 1.0121 0.3831 0.0807 0.053 Uiso 1 1 calc R . . H25C H 1.2274 0.4333 0.1290 0.053 Uiso 1 1 calc R . . C26 C 1.1420(3) 0.47861(19) 0.30413(18) 0.0308(5) Uani 1 1 d . . . H26A H 1.1333 0.5545 0.2973 0.046 Uiso 1 1 calc R . . H26B H 1.2787 0.4741 0.2990 0.046 Uiso 1 1 calc R . . H26C H 1.0974 0.4562 0.3657 0.046 Uiso 1 1 calc R . . C27 C 0.8012(3) 0.41685(19) 0.23040(16) 0.0262(5) Uani 1 1 d . . . H27A H 0.7481 0.3942 0.2904 0.039 Uiso 1 1 calc R . . H27B H 0.7185 0.3715 0.1787 0.039 Uiso 1 1 calc R . . H27C H 0.8027 0.4944 0.2245 0.039 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 Br1 0.02295(14) 0.03528(17) 0.02332(15) -0.00089(9) 0.00546(9) 0.01286(10) Si1 0.0161(3) 0.0206(3) 0.0177(3) 0.0014(2) 0.0030(2) 0.0039(2) O1 0.0174(7) 0.0214(8) 0.0195(7) 0.0015(5) 0.0039(5) 0.0024(5) C2 0.0172(9) 0.0228(11) 0.0175(10) 0.0043(7) 0.0027(7) 0.0039(8) C3 0.0206(10) 0.0260(12) 0.0260(11) 0.0061(8) 0.0073(8) 0.0058(8) C4 0.0230(10) 0.0220(12) 0.0251(11) 0.0046(8) 0.0048(8) 0.0040(8) C5 0.0227(11) 0.0203(11) 0.0266(11) 0.0032(8) 0.0026(8) 0.0037(8) C6 0.0199(10) 0.0225(11) 0.0164(9) 0.0050(7) 0.0011(7) 0.0061(8) C7 0.0161(9) 0.0258(11) 0.0188(10) 0.0018(8) 0.0000(7) 0.0030(8) C8 0.0225(10) 0.0228(11) 0.0183(10) -0.0016(8) -0.0017(8) 0.0059(8) C9 0.0181(9) 0.0281(11) 0.0158(9) 0.0025(8) 0.0031(7) 0.0113(8) C10 0.0175(9) 0.0260(11) 0.0200(10) 0.0046(8) 0.0025(8) 0.0048(8) C11 0.0195(10) 0.0227(11) 0.0196(10) 0.0026(8) 0.0014(8) 0.0043(8) C12 0.0161(9) 0.0239(11) 0.0235(10) -0.0011(8) 0.0014(8) 0.0030(8) C13 0.0256(11) 0.0290(12) 0.0195(10) 0.0030(8) 0.0038(8) 0.0073(9) C14 0.0255(11) 0.0251(12) 0.0216(10) 0.0038(8) 0.0011(8) 0.0092(8) C15 0.0178(10) 0.0257(11) 0.0205(10) -0.0004(8) 0.0001(8) 0.0052(8) C16 0.0225(10) 0.0303(12) 0.0190(10) 0.0053(8) 0.0032(8) 0.0077(8) C17 0.0236(10) 0.0221(11) 0.0259(11) 0.0042(8) 0.0014(8) 0.0077(8) C18 0.0238(10) 0.0267(12) 0.0221(10) 0.0020(8) 0.0016(8) 0.0093(8) C19 0.0247(11) 0.0339(14) 0.0412(14) -0.0008(10) 0.0113(10) 0.0067(9) C20 0.0302(12) 0.0339(13) 0.0288(12) -0.0057(10) 0.0050(9) 0.0062(9) C21 0.0455(15) 0.0540(17) 0.0305(13) 0.0086(11) 0.0088(11) 0.0347(13) C22 0.0267(11) 0.0269(12) 0.0238(11) -0.0006(8) -0.0009(9) 0.0041(9) C23 0.0184(10) 0.0325(12) 0.0258(11) 0.0060(9) 0.0067(8) 0.0073(8) C24 0.0241(11) 0.0226(11) 0.0231(11) 0.0022(8) 0.0053(8) 0.0054(8) C25 0.0446(14) 0.0319(14) 0.0340(13) 0.0132(10) 0.0162(11) 0.0121(11) C26 0.0275(12) 0.0219(12) 0.0392(13) -0.0027(9) 0.0038(10) -0.0002(9) C27 0.0289(11) 0.0276(12) 0.0246(11) 0.0028(8) 0.0021(9) 0.0117(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 Br1 C9 1.901(2) . ? Si1 O1 1.6742(14) . ? Si1 C23 1.853(2) . ? Si1 C22 1.862(2) . ? Si1 C24 1.885(2) . ? O1 C2 1.361(2) . ? C2 C3 1.346(3) . ? C2 C6 1.477(3) . ? C3 C4 1.421(3) . ? C3 H3 0.9500 . ? C4 C5 1.209(3) . ? C5 C12 1.435(3) . ? C6 C7 1.400(3) . ? C6 C11 1.401(3) . ? C7 C8 1.383(3) . ? C7 H7 0.9500 . ? C8 C9 1.388(3) . ? C8 H8 0.9500 . ? C9 C10 1.381(3) . ? C10 C11 1.390(3) . ? C10 H10 0.9500 . ? C11 H11 0.9500 . ? C12 C13 1.393(3) . ? C12 C17 1.406(3) . ? C13 C14 1.384(3) . ? C13 H13 0.9500 . ? C14 C15 1.402(3) . ? C14 H14 0.9500 . ? C15 C16 1.399(3) . ? C15 C18 1.528(3) . ? C16 C17 1.376(3) . ? C16 H16 0.9500 . ? C17 H17 0.9500 . ? C18 C21 1.530(3) . ? C18 C19 1.532(3) . ? C18 C20 1.538(3) . ? C19 H19A 0.9800 . ? C19 H19B 0.9800 . ? C19 H19C 0.9800 . ? C20 H20A 0.9800 . ? C20 H20B 0.9800 . ? C20 H20C 0.9800 . ? C21 H21A 0.9800 . ? C21 H21B 0.9800 . ? C21 H21C 0.9800 . ? C22 H22A 0.9800 . ? C22 H22B 0.9800 . ? C22 H22C 0.9800 . ? C23 H23A 0.9800 . ? C23 H23B 0.9800 . ? C23 H23C 0.9800 . ? C24 C26 1.536(3) . ? C24 C27 1.536(3) . ? C24 C25 1.540(3) . ? C25 H25A 0.9800 . ? C25 H25B 0.9800 . ? C25 H25C 0.9800 . ? C26 H26A 0.9800 . ? C26 H26B 0.9800 . ? C26 H26C 0.9800 . ? C27 H27A 0.9800 . ? C27 H27B 0.9800 . ? C27 H27C 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 Si1 C23 107.89(9) . . ? O1 Si1 C22 109.04(9) . . ? C23 Si1 C22 112.71(11) . . ? O1 Si1 C24 105.91(9) . . ? C23 Si1 C24 109.93(10) . . ? C22 Si1 C24 111.09(10) . . ? C2 O1 Si1 130.81(13) . . ? C3 C2 O1 122.16(19) . . ? C3 C2 C6 123.12(18) . . ? O1 C2 C6 114.60(18) . . ? C2 C3 C4 124.92(19) . . ? C2 C3 H3 117.5 . . ? C4 C3 H3 117.5 . . ? C5 C4 C3 178.2(2) . . ? C4 C5 C12 176.3(2) . . ? C7 C6 C11 118.5(2) . . ? C7 C6 C2 119.59(18) . . ? C11 C6 C2 121.96(19) . . ? C8 C7 C6 121.19(19) . . ? C8 C7 H7 119.4 . . ? C6 C7 H7 119.4 . . ? C7 C8 C9 118.9(2) . . ? C7 C8 H8 120.6 . . ? C9 C8 H8 120.6 . . ? C10 C9 C8 121.61(19) . . ? C10 C9 Br1 119.72(15) . . ? C8 C9 Br1 118.67(16) . . ? C9 C10 C11 119.08(19) . . ? C9 C10 H10 120.5 . . ? C11 C10 H10 120.5 . . ? C10 C11 C6 120.8(2) . . ? C10 C11 H11 119.6 . . ? C6 C11 H11 119.6 . . ? C13 C12 C17 118.0(2) . . ? C13 C12 C5 122.2(2) . . ? C17 C12 C5 119.8(2) . . ? C14 C13 C12 120.8(2) . . ? C14 C13 H13 119.6 . . ? C12 C13 H13 119.6 . . ? C13 C14 C15 121.7(2) . . ? C13 C14 H14 119.1 . . ? C15 C14 H14 119.1 . . ? C16 C15 C14 116.9(2) . . ? C16 C15 C18 120.03(19) . . ? C14 C15 C18 123.00(19) . . ? C17 C16 C15 121.9(2) . . ? C17 C16 H16 119.1 . . ? C15 C16 H16 119.1 . . ? C16 C17 C12 120.8(2) . . ? C16 C17 H17 119.6 . . ? C12 C17 H17 119.6 . . ? C15 C18 C21 112.60(18) . . ? C15 C18 C19 110.24(18) . . ? C21 C18 C19 108.0(2) . . ? C15 C18 C20 108.42(17) . . ? C21 C18 C20 108.8(2) . . ? C19 C18 C20 108.70(19) . . ? C18 C19 H19A 109.5 . . ? C18 C19 H19B 109.5 . . ? H19A C19 H19B 109.5 . . ? C18 C19 H19C 109.5 . . ? H19A C19 H19C 109.5 . . ? H19B C19 H19C 109.5 . . ? C18 C20 H20A 109.5 . . ? C18 C20 H20B 109.5 . . ? H20A C20 H20B 109.5 . . ? C18 C20 H20C 109.5 . . ? H20A C20 H20C 109.5 . . ? H20B C20 H20C 109.5 . . ? C18 C21 H21A 109.5 . . ? C18 C21 H21B 109.5 . . ? H21A C21 H21B 109.5 . . ? C18 C21 H21C 109.5 . . ? H21A C21 H21C 109.5 . . ? H21B C21 H21C 109.5 . . ? Si1 C22 H22A 109.5 . . ? Si1 C22 H22B 109.5 . . ? H22A C22 H22B 109.5 . . ? Si1 C22 H22C 109.5 . . ? H22A C22 H22C 109.5 . . ? H22B C22 H22C 109.5 . . ? Si1 C23 H23A 109.5 . . ? Si1 C23 H23B 109.5 . . ? H23A C23 H23B 109.5 . . ? Si1 C23 H23C 109.5 . . ? H23A C23 H23C 109.5 . . ? H23B C23 H23C 109.5 . . ? C26 C24 C27 108.85(19) . . ? C26 C24 C25 108.89(19) . . ? C27 C24 C25 108.24(19) . . ? C26 C24 Si1 110.40(16) . . ? C27 C24 Si1 110.53(15) . . ? C25 C24 Si1 109.88(16) . . ? C24 C25 H25A 109.5 . . ? C24 C25 H25B 109.5 . . ? H25A C25 H25B 109.5 . . ? C24 C25 H25C 109.5 . . ? H25A C25 H25C 109.5 . . ? H25B C25 H25C 109.5 . . ? C24 C26 H26A 109.5 . . ? C24 C26 H26B 109.5 . . ? H26A C26 H26B 109.5 . . ? C24 C26 H26C 109.5 . . ? H26A C26 H26C 109.5 . . ? H26B C26 H26C 109.5 . . ? C24 C27 H27A 109.5 . . ? C24 C27 H27B 109.5 . . ? H27A C27 H27B 109.5 . . ? C24 C27 H27C 109.5 . . ? H27A C27 H27C 109.5 . . ? H27B C27 H27C 109.5 . . ? 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 C23 Si1 O1 C2 -119.74(18) . . . . ? C22 Si1 O1 C2 3.0(2) . . . . ? C24 Si1 O1 C2 122.59(18) . . . . ? Si1 O1 C2 C3 68.1(3) . . . . ? Si1 O1 C2 C6 -115.74(18) . . . . ? O1 C2 C3 C4 -2.1(3) . . . . ? C6 C2 C3 C4 -178.0(2) . . . . ? C2 C3 C4 C5 158(8) . . . . ? C3 C4 C5 C12 143(7) . . . . ? C3 C2 C6 C7 157.3(2) . . . . ? O1 C2 C6 C7 -18.8(3) . . . . ? C3 C2 C6 C11 -23.1(3) . . . . ? O1 C2 C6 C11 160.74(18) . . . . ? C11 C6 C7 C8 0.9(3) . . . . ? C2 C6 C7 C8 -179.47(18) . . . . ? C6 C7 C8 C9 -0.4(3) . . . . ? C7 C8 C9 C10 -0.6(3) . . . . ? C7 C8 C9 Br1 179.72(15) . . . . ? C8 C9 C10 C11 1.2(3) . . . . ? Br1 C9 C10 C11 -179.20(15) . . . . ? C9 C10 C11 C6 -0.6(3) . . . . ? C7 C6 C11 C10 -0.4(3) . . . . ? C2 C6 C11 C10 -179.98(18) . . . . ? C4 C5 C12 C13 -171(3) . . . . ? C4 C5 C12 C17 8(4) . . . . ? C17 C12 C13 C14 -1.3(3) . . . . ? C5 C12 C13 C14 177.8(2) . . . . ? C12 C13 C14 C15 -0.3(3) . . . . ? C13 C14 C15 C16 1.3(3) . . . . ? C13 C14 C15 C18 -175.6(2) . . . . ? C14 C15 C16 C17 -0.7(3) . . . . ? C18 C15 C16 C17 176.3(2) . . . . ? C15 C16 C17 C12 -0.8(3) . . . . ? C13 C12 C17 C16 1.8(3) . . . . ? C5 C12 C17 C16 -177.3(2) . . . . ? C16 C15 C18 C21 172.2(2) . . . . ? C14 C15 C18 C21 -11.0(3) . . . . ? C16 C15 C18 C19 51.5(3) . . . . ? C14 C15 C18 C19 -131.7(2) . . . . ? C16 C15 C18 C20 -67.4(3) . . . . ? C14 C15 C18 C20 109.4(2) . . . . ? O1 Si1 C24 C26 55.74(16) . . . . ? C23 Si1 C24 C26 -60.56(17) . . . . ? C22 Si1 C24 C26 174.00(15) . . . . ? O1 Si1 C24 C27 -64.74(16) . . . . ? C23 Si1 C24 C27 178.95(15) . . . . ? C22 Si1 C24 C27 53.51(18) . . . . ? O1 Si1 C24 C25 175.86(15) . . . . ? C23 Si1 C24 C25 59.56(19) . . . . ? C22 Si1 C24 C25 -65.88(19) . . . . ? _diffrn_measured_fraction_theta_max 0.971 _diffrn_reflns_theta_full 68.23 _diffrn_measured_fraction_theta_full 0.971 _refine_diff_density_max 0.799 _refine_diff_density_min -0.313 _refine_diff_density_rms 0.083 data_demb17 _database_code_depnum_ccdc_archive 'CCDC 826571' #TrackingRef '- DEMB17_pub.CIF' _audit_creation_method SHELXL-97 _chemical_name_systematic ; 3-bromo-4-fluoro-2-(4-methylphenyl)-5-phenylfuran ; _chemical_name_common 3-bromo-4-fluoro-2-(4-methylphenyl)-5-phenylfuran _chemical_melting_point ? _chemical_formula_moiety 'C17 H12 Br F O' _chemical_formula_sum 'C17 H12 Br F O' _chemical_formula_weight 331.18 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0181 0.0091 '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 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' F F 0.0727 0.0534 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Br Br -0.6763 1.2805 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Monoclinic _symmetry_space_group_name_H-M 'C 2/c' _symmetry_space_group_name_Hall '-C 2yc' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y, -z+1/2' 'x+1/2, y+1/2, z' '-x+1/2, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y, z-1/2' '-x+1/2, -y+1/2, -z' 'x+1/2, -y+1/2, z-1/2' _cell_length_a 33.7073(6) _cell_length_b 5.6320(1) _cell_length_c 14.5599(3) _cell_angle_alpha 90.00 _cell_angle_beta 97.857(1) _cell_angle_gamma 90.00 _cell_volume 2738.10(9) _cell_formula_units_Z 8 _cell_measurement_temperature 100(2) _cell_measurement_reflns_used 8120 _cell_measurement_theta_min 2.639 _cell_measurement_theta_max 70.688 _exptl_crystal_description 'transparent needle' _exptl_crystal_colour colorless _exptl_crystal_size_max 0.38 _exptl_crystal_size_mid 0.11 _exptl_crystal_size_min 0.04 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.607 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1328 _exptl_absorpt_coefficient_mu 4.131 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.3014 _exptl_absorpt_correction_T_max 0.8555 _exptl_absorpt_process_details 'SADABS v2.05(Bruker, 2009)' _exptl_special_details ; ? ; _diffrn_ambient_temperature 100(2) _diffrn_radiation_wavelength 1.54178 _diffrn_radiation_type CuK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Bruker SMART APEXII CCD' _diffrn_measurement_method 'phi and omega scans' _diffrn_detector_area_resol_mean . _diffrn_standards_number . _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% . _diffrn_reflns_number 18001 _diffrn_reflns_av_R_equivalents 0.0401 _diffrn_reflns_av_sigmaI/netI 0.0220 _diffrn_reflns_limit_h_min -40 _diffrn_reflns_limit_h_max 40 _diffrn_reflns_limit_k_min -5 _diffrn_reflns_limit_k_max 6 _diffrn_reflns_limit_l_min -17 _diffrn_reflns_limit_l_max 17 _diffrn_reflns_theta_min 2.65 _diffrn_reflns_theta_max 68.20 _reflns_number_total 2486 _reflns_number_gt 2168 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'SMART (Bruker, 2009)' _computing_cell_refinement 'SMART (Bruker, 2009)' _computing_data_reduction ; 'SAINT (Bruker, 2002) and XPREP (Bruker, 2001)' ; _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'X-SEED (Barbour, 2001)' _computing_publication_material 'X-SEED (Barbour, 2001)' _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^)+(0.0433P)^2^+7.9011P] 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 2486 _refine_ls_number_parameters 182 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0411 _refine_ls_R_factor_gt 0.0342 _refine_ls_wR_factor_ref 0.0890 _refine_ls_wR_factor_gt 0.0854 _refine_ls_goodness_of_fit_ref 1.098 _refine_ls_restrained_S_all 1.098 _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 Br1 Br 0.105293(10) 0.18962(6) 0.65962(2) 0.02960(13) Uani 1 1 d . . . F1 F 0.04188(5) 0.5707(3) 0.72067(12) 0.0311(4) Uani 1 1 d . . . O1 O 0.13371(6) 0.6656(4) 0.86775(14) 0.0253(5) Uani 1 1 d . . . C2 C 0.09413(9) 0.7240(6) 0.8403(2) 0.0261(7) Uani 1 1 d . . . C3 C 0.08022(9) 0.5750(6) 0.7704(2) 0.0270(7) Uani 1 1 d . . . C4 C 0.11119(9) 0.4196(6) 0.75379(19) 0.0247(6) Uani 1 1 d . . . C5 C 0.14390(9) 0.4781(5) 0.8148(2) 0.0241(6) Uani 1 1 d . . . C6 C 0.07772(9) 0.9216(6) 0.8871(2) 0.0264(6) Uani 1 1 d . . . C7 C 0.10283(9) 1.0666(6) 0.9479(2) 0.0275(7) Uani 1 1 d . . . H7 H 0.1307 1.0344 0.9592 0.033 Uiso 1 1 calc R . . C8 C 0.08730(10) 1.2557(6) 0.9914(2) 0.0303(7) Uani 1 1 d . . . H8 H 0.1046 1.3535 1.0323 0.036 Uiso 1 1 calc R . . C9 C 0.04647(10) 1.3043(6) 0.9758(2) 0.0353(8) Uani 1 1 d . . . H9 H 0.0358 1.4340 1.0062 0.042 Uiso 1 1 calc R . . C10 C 0.02168(11) 1.1622(7) 0.9159(3) 0.0451(10) Uani 1 1 d . . . H10 H -0.0062 1.1960 0.9045 0.054 Uiso 1 1 calc R . . C11 C 0.03678(10) 0.9716(7) 0.8721(2) 0.0374(8) Uani 1 1 d . . . H11 H 0.0192 0.8742 0.8316 0.045 Uiso 1 1 calc R . . C12 C 0.18501(9) 0.3970(5) 0.8354(2) 0.0234(6) Uani 1 1 d . . . C13 C 0.19785(10) 0.1773(6) 0.8057(2) 0.0271(7) Uani 1 1 d . . . H13 H 0.1791 0.0741 0.7711 0.033 Uiso 1 1 calc R . . C14 C 0.23749(9) 0.1086(6) 0.8261(2) 0.0253(6) Uani 1 1 d . . . H14 H 0.2454 -0.0413 0.8049 0.030 Uiso 1 1 calc R . . C15 C 0.26606(9) 0.2529(6) 0.8767(2) 0.0266(7) Uani 1 1 d . . . C16 C 0.25318(9) 0.4706(6) 0.9073(2) 0.0280(7) Uani 1 1 d . . . H16 H 0.2720 0.5721 0.9426 0.034 Uiso 1 1 calc R . . C17 C 0.21385(9) 0.5419(6) 0.8875(2) 0.0265(6) Uani 1 1 d . . . H17 H 0.2060 0.6914 0.9094 0.032 Uiso 1 1 calc R . . C18 C 0.30918(9) 0.1788(6) 0.8969(2) 0.0313(7) Uani 1 1 d . . . H18A H 0.3124 0.0198 0.8716 0.047 Uiso 1 1 calc R . . H18B H 0.3174 0.1767 0.9641 0.047 Uiso 1 1 calc R . . H18C H 0.3259 0.2917 0.8682 0.047 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 Br1 0.0345(2) 0.0265(2) 0.02661(19) -0.00486(13) -0.00001(13) -0.00211(14) F1 0.0284(9) 0.0323(11) 0.0316(9) -0.0016(8) 0.0008(7) 0.0085(8) O1 0.0269(11) 0.0218(11) 0.0269(11) -0.0017(8) 0.0026(8) 0.0010(9) C2 0.0231(15) 0.0282(17) 0.0266(15) 0.0042(13) 0.0014(12) 0.0002(12) C3 0.0263(15) 0.0298(18) 0.0242(15) 0.0016(13) 0.0011(12) -0.0002(13) C4 0.0318(16) 0.0204(15) 0.0218(14) -0.0027(12) 0.0028(12) -0.0023(13) C5 0.0309(16) 0.0191(16) 0.0233(14) 0.0003(11) 0.0071(12) -0.0017(12) C6 0.0299(16) 0.0246(16) 0.0245(15) 0.0021(13) 0.0035(12) 0.0010(13) C7 0.0250(15) 0.0291(18) 0.0278(15) 0.0009(13) 0.0014(12) 0.0005(13) C8 0.0311(17) 0.0278(17) 0.0316(16) -0.0020(13) 0.0026(13) 0.0006(13) C9 0.0353(18) 0.032(2) 0.0386(19) -0.0036(15) 0.0057(14) 0.0048(15) C10 0.0287(17) 0.051(3) 0.054(2) -0.0122(19) -0.0002(16) 0.0094(16) C11 0.0276(17) 0.041(2) 0.0409(19) -0.0109(16) -0.0047(14) 0.0024(15) C12 0.0306(15) 0.0200(16) 0.0204(14) 0.0019(11) 0.0056(12) -0.0003(12) C13 0.0328(16) 0.0235(17) 0.0247(15) -0.0022(12) 0.0026(12) -0.0038(13) C14 0.0327(16) 0.0192(16) 0.0244(15) -0.0001(12) 0.0052(12) 0.0011(12) C15 0.0319(16) 0.0289(17) 0.0195(14) 0.0042(12) 0.0053(12) -0.0007(13) C16 0.0323(16) 0.0275(18) 0.0241(15) -0.0018(12) 0.0029(12) -0.0063(13) C17 0.0307(16) 0.0210(16) 0.0282(15) -0.0026(12) 0.0059(13) -0.0010(13) C18 0.0303(16) 0.0339(19) 0.0292(16) 0.0007(14) 0.0030(13) 0.0006(14) _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 Br1 C4 1.877(3) . ? F1 C3 1.392(3) . ? O1 C5 1.378(4) . ? O1 C2 1.379(4) . ? C2 C3 1.353(4) . ? C2 C6 1.453(5) . ? C3 C4 1.408(4) . ? C4 C5 1.358(4) . ? C5 C12 1.451(4) . ? C6 C11 1.396(4) . ? C6 C7 1.401(4) . ? C7 C8 1.379(5) . ? C7 H7 0.9500 . ? C8 C9 1.391(5) . ? C8 H8 0.9500 . ? C9 C10 1.379(5) . ? C9 H9 0.9500 . ? C10 C11 1.381(5) . ? C10 H10 0.9500 . ? C11 H11 0.9500 . ? C12 C13 1.399(4) . ? C12 C17 1.409(4) . ? C13 C14 1.383(4) . ? C13 H13 0.9500 . ? C14 C15 1.392(4) . ? C14 H14 0.9500 . ? C15 C16 1.394(5) . ? C15 C18 1.502(4) . ? C16 C17 1.377(4) . ? C16 H16 0.9500 . ? C17 H17 0.9500 . ? C18 H18A 0.9800 . ? C18 H18B 0.9800 . ? C18 H18C 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 C5 O1 C2 109.0(2) . . ? C3 C2 O1 107.0(3) . . ? C3 C2 C6 135.5(3) . . ? O1 C2 C6 117.5(3) . . ? C2 C3 F1 127.1(3) . . ? C2 C3 C4 109.0(3) . . ? F1 C3 C4 123.9(3) . . ? C5 C4 C3 106.9(3) . . ? C5 C4 Br1 129.8(2) . . ? C3 C4 Br1 123.2(2) . . ? C4 C5 O1 108.1(3) . . ? C4 C5 C12 136.5(3) . . ? O1 C5 C12 115.4(3) . . ? C11 C6 C7 118.7(3) . . ? C11 C6 C2 120.9(3) . . ? C7 C6 C2 120.5(3) . . ? C8 C7 C6 120.4(3) . . ? C8 C7 H7 119.8 . . ? C6 C7 H7 119.8 . . ? C7 C8 C9 120.4(3) . . ? C7 C8 H8 119.8 . . ? C9 C8 H8 119.8 . . ? C10 C9 C8 119.3(3) . . ? C10 C9 H9 120.3 . . ? C8 C9 H9 120.3 . . ? C9 C10 C11 120.9(3) . . ? C9 C10 H10 119.5 . . ? C11 C10 H10 119.5 . . ? C10 C11 C6 120.3(3) . . ? C10 C11 H11 119.9 . . ? C6 C11 H11 119.9 . . ? C13 C12 C17 117.3(3) . . ? C13 C12 C5 122.8(3) . . ? C17 C12 C5 119.9(3) . . ? C14 C13 C12 120.8(3) . . ? C14 C13 H13 119.6 . . ? C12 C13 H13 119.6 . . ? C13 C14 C15 121.9(3) . . ? C13 C14 H14 119.1 . . ? C15 C14 H14 119.1 . . ? C14 C15 C16 117.4(3) . . ? C14 C15 C18 121.5(3) . . ? C16 C15 C18 121.1(3) . . ? C17 C16 C15 121.5(3) . . ? C17 C16 H16 119.2 . . ? C15 C16 H16 119.2 . . ? C16 C17 C12 121.1(3) . . ? C16 C17 H17 119.4 . . ? C12 C17 H17 119.4 . . ? C15 C18 H18A 109.5 . . ? C15 C18 H18B 109.5 . . ? H18A C18 H18B 109.5 . . ? C15 C18 H18C 109.5 . . ? H18A C18 H18C 109.5 . . ? H18B C18 H18C 109.5 . . ? 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 C5 O1 C2 C3 -0.6(3) . . . . ? C5 O1 C2 C6 -179.0(3) . . . . ? O1 C2 C3 F1 -179.2(3) . . . . ? C6 C2 C3 F1 -1.3(6) . . . . ? O1 C2 C3 C4 0.4(3) . . . . ? C6 C2 C3 C4 178.4(3) . . . . ? C2 C3 C4 C5 -0.1(4) . . . . ? F1 C3 C4 C5 179.6(3) . . . . ? C2 C3 C4 Br1 -177.9(2) . . . . ? F1 C3 C4 Br1 1.7(4) . . . . ? C3 C4 C5 O1 -0.3(3) . . . . ? Br1 C4 C5 O1 177.4(2) . . . . ? C3 C4 C5 C12 -179.1(3) . . . . ? Br1 C4 C5 C12 -1.5(6) . . . . ? C2 O1 C5 C4 0.5(3) . . . . ? C2 O1 C5 C12 179.7(2) . . . . ? C3 C2 C6 C11 10.8(6) . . . . ? O1 C2 C6 C11 -171.5(3) . . . . ? C3 C2 C6 C7 -168.9(4) . . . . ? O1 C2 C6 C7 8.9(4) . . . . ? C11 C6 C7 C8 -0.4(5) . . . . ? C2 C6 C7 C8 179.2(3) . . . . ? C6 C7 C8 C9 0.3(5) . . . . ? C7 C8 C9 C10 -0.4(5) . . . . ? C8 C9 C10 C11 0.7(6) . . . . ? C9 C10 C11 C6 -0.9(6) . . . . ? C7 C6 C11 C10 0.7(5) . . . . ? C2 C6 C11 C10 -179.0(3) . . . . ? C4 C5 C12 C13 -17.3(5) . . . . ? O1 C5 C12 C13 163.9(3) . . . . ? C4 C5 C12 C17 162.7(3) . . . . ? O1 C5 C12 C17 -16.1(4) . . . . ? C17 C12 C13 C14 -0.8(4) . . . . ? C5 C12 C13 C14 179.2(3) . . . . ? C12 C13 C14 C15 0.2(5) . . . . ? C13 C14 C15 C16 0.6(4) . . . . ? C13 C14 C15 C18 -178.8(3) . . . . ? C14 C15 C16 C17 -0.6(4) . . . . ? C18 C15 C16 C17 178.7(3) . . . . ? C15 C16 C17 C12 0.0(5) . . . . ? C13 C12 C17 C16 0.7(4) . . . . ? C5 C12 C17 C16 -179.3(3) . . . . ? _diffrn_measured_fraction_theta_max 0.991 _diffrn_reflns_theta_full 68.20 _diffrn_measured_fraction_theta_full 0.991 _refine_diff_density_max 1.228 _refine_diff_density_min -0.217 _refine_diff_density_rms 0.077 #===END # Attachment '- DEMB18a_pub.CIF' data_demb18a _database_code_depnum_ccdc_archive 'CCDC 827011' #TrackingRef '- DEMB18a_pub.CIF' _audit_creation_method SHELXL-97 _chemical_name_systematic ; 3-fluoro-5-(4-methylphenyl)-2-phenyl-4-(phenylethynyl)furan ; _chemical_name_common 3-fluoro-5-(4-methylphenyl)-2-phenyl-4-(phenylethynyl)furan _chemical_melting_point ? _chemical_formula_moiety 'C25 H17 F O' _chemical_formula_sum 'C25 H17 F O' _chemical_formula_weight 352.39 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0181 0.0091 '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 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' F F 0.0727 0.0534 '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_space_group_name_Hall '-P 2ybc' 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 13.0824(6) _cell_length_b 5.1563(2) _cell_length_c 26.5341(12) _cell_angle_alpha 90.00 _cell_angle_beta 93.297(3) _cell_angle_gamma 90.00 _cell_volume 1786.94(13) _cell_formula_units_Z 4 _cell_measurement_temperature 100(2) _cell_measurement_reflns_used 5647 _cell_measurement_theta_min 3.345 _cell_measurement_theta_max 66.194 _exptl_crystal_description 'transparent needle' _exptl_crystal_colour colorless _exptl_crystal_size_max 0.52 _exptl_crystal_size_mid 0.31 _exptl_crystal_size_min 0.23 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.310 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 736 _exptl_absorpt_coefficient_mu 0.685 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.7158 _exptl_absorpt_correction_T_max 0.8561 _exptl_absorpt_process_details 'SADABS (Bruker, 2010)' _exptl_special_details ; ? ; _diffrn_ambient_temperature 100(2) _diffrn_radiation_wavelength 1.54178 _diffrn_radiation_type CuK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Bruker APEXII CCD' _diffrn_measurement_method 'phi and omega scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count . _diffrn_standards_interval_time . _diffrn_standards_decay_% ? _diffrn_reflns_number 23456 _diffrn_reflns_av_R_equivalents 0.0760 _diffrn_reflns_av_sigmaI/netI 0.0381 _diffrn_reflns_limit_h_min -15 _diffrn_reflns_limit_h_max 15 _diffrn_reflns_limit_k_min -5 _diffrn_reflns_limit_k_max 6 _diffrn_reflns_limit_l_min -31 _diffrn_reflns_limit_l_max 31 _diffrn_reflns_theta_min 3.34 _diffrn_reflns_theta_max 67.59 _reflns_number_total 3205 _reflns_number_gt 2279 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'APEX2 (Bruker, 2010)' _computing_cell_refinement APEX2 _computing_data_reduction ; SAINT (Bruker, 2008) and XPREP (Bruker, 2008) ; _computing_structure_solution 'SHELXS-97 (Sheldrick, 2008)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 2008)' _computing_molecular_graphics 'XSEED (Barbour, 2001)' _computing_publication_material 'XSEED (Barbour, 2001)' _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. All non-hydrogen atoms were located in a difference Fourier map and refined using anisotropic displacement parameters. The hydrogen atoms were placed in fixed positions with Ueq = 1.2xUiso of the carbon atom to which they are attached (Ueq = 1.5xUiso for methyl groups). ; _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^)+(0.0464P)^2^+0.3177P] 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 3205 _refine_ls_number_parameters 245 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0668 _refine_ls_R_factor_gt 0.0384 _refine_ls_wR_factor_ref 0.0962 _refine_ls_wR_factor_gt 0.0851 _refine_ls_goodness_of_fit_ref 1.010 _refine_ls_restrained_S_all 1.010 _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 F1 F 0.08842(8) 0.9047(2) 0.27175(3) 0.0351(3) Uani 1 1 d . . . O1 O 0.11319(9) 0.6752(2) 0.39611(4) 0.0260(3) Uani 1 1 d . . . C2 C 0.07000(13) 0.8427(3) 0.36046(6) 0.0255(4) Uani 1 1 d . . . C3 C 0.11013(13) 0.7846(3) 0.31606(6) 0.0274(4) Uani 1 1 d . . . C4 C 0.17986(13) 0.5758(4) 0.32246(6) 0.0281(4) Uani 1 1 d . . . C5 C 0.17950(13) 0.5142(3) 0.37301(6) 0.0269(4) Uani 1 1 d . . . C6 C -0.00255(12) 1.0335(3) 0.37670(6) 0.0255(4) Uani 1 1 d . . . C7 C -0.02612(13) 1.0541(4) 0.42707(6) 0.0301(4) Uani 1 1 d . . . H7 H 0.0040 0.9375 0.4514 0.036 Uiso 1 1 calc R . . C8 C -0.09302(14) 1.2429(4) 0.44196(7) 0.0343(4) Uani 1 1 d . . . H8 H -0.1077 1.2569 0.4765 0.041 Uiso 1 1 calc R . . C9 C -0.13889(14) 1.4117(4) 0.40697(7) 0.0343(4) Uani 1 1 d . . . H9 H -0.1850 1.5409 0.4173 0.041 Uiso 1 1 calc R . . C10 C -0.11697(14) 1.3906(4) 0.35678(7) 0.0336(4) Uani 1 1 d . . . H10 H -0.1485 1.5054 0.3326 0.040 Uiso 1 1 calc R . . C11 C -0.04957(13) 1.2041(4) 0.34153(7) 0.0307(4) Uani 1 1 d . . . H11 H -0.0350 1.1916 0.3069 0.037 Uiso 1 1 calc R . . C12 C 0.23244(12) 0.3227(3) 0.40515(6) 0.0269(4) Uani 1 1 d . . . C13 C 0.21060(14) 0.2978(4) 0.45574(7) 0.0311(4) Uani 1 1 d . . . H13 H 0.1604 0.4065 0.4693 0.037 Uiso 1 1 calc R . . C14 C 0.26119(14) 0.1165(4) 0.48635(7) 0.0328(4) Uani 1 1 d . . . H14 H 0.2455 0.1047 0.5208 0.039 Uiso 1 1 calc R . . C15 C 0.33425(13) -0.0489(4) 0.46814(7) 0.0334(4) Uani 1 1 d . . . C16 C 0.35491(14) -0.0251(4) 0.41744(8) 0.0371(5) Uani 1 1 d . . . H16 H 0.4042 -0.1364 0.4038 0.045 Uiso 1 1 calc R . . C17 C 0.30519(14) 0.1571(4) 0.38654(7) 0.0332(4) Uani 1 1 d . . . H17 H 0.3210 0.1692 0.3521 0.040 Uiso 1 1 calc R . . C18 C 0.38952(15) -0.2455(4) 0.50181(8) 0.0426(5) Uani 1 1 d . . . H18A H 0.4543 -0.1715 0.5155 0.064 Uiso 1 1 calc R . . H18B H 0.4034 -0.4012 0.4822 0.064 Uiso 1 1 calc R . . H18C H 0.3468 -0.2914 0.5296 0.064 Uiso 1 1 calc R . . C19 C 0.23548(13) 0.4595(4) 0.28381(7) 0.0298(4) Uani 1 1 d . . . C20 C 0.28015(14) 0.3659(4) 0.25008(7) 0.0311(4) Uani 1 1 d . . . C21 C 0.33605(13) 0.2496(4) 0.21092(6) 0.0278(4) Uani 1 1 d . . . C22 C 0.33084(13) 0.3543(4) 0.16221(7) 0.0309(4) Uani 1 1 d . . . H22 H 0.2892 0.5018 0.1547 0.037 Uiso 1 1 calc R . . C23 C 0.38640(13) 0.2429(4) 0.12501(7) 0.0322(4) Uani 1 1 d . . . H23 H 0.3828 0.3148 0.0920 0.039 Uiso 1 1 calc R . . C24 C 0.44689(14) 0.0285(4) 0.13547(7) 0.0331(4) Uani 1 1 d . . . H24 H 0.4848 -0.0467 0.1097 0.040 Uiso 1 1 calc R . . C25 C 0.45244(14) -0.0772(4) 0.18347(7) 0.0340(4) Uani 1 1 d . . . H25 H 0.4944 -0.2245 0.1907 0.041 Uiso 1 1 calc R . . C26 C 0.39685(14) 0.0316(4) 0.22100(7) 0.0317(4) Uani 1 1 d . . . H26 H 0.4002 -0.0428 0.2538 0.038 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 F1 0.0445(6) 0.0391(6) 0.0216(5) 0.0015(4) 0.0007(4) 0.0008(5) O1 0.0263(6) 0.0279(7) 0.0236(6) -0.0010(5) 0.0014(5) 0.0031(5) C2 0.0252(9) 0.0270(9) 0.0240(9) 0.0008(7) -0.0021(7) -0.0020(8) C3 0.0306(9) 0.0302(10) 0.0213(9) 0.0004(7) -0.0004(7) -0.0032(8) C4 0.0286(9) 0.0297(10) 0.0262(9) -0.0056(8) 0.0038(7) -0.0049(8) C5 0.0239(9) 0.0276(10) 0.0294(9) -0.0052(8) 0.0025(7) -0.0010(8) C6 0.0230(8) 0.0264(9) 0.0270(9) -0.0008(7) 0.0000(7) -0.0028(8) C7 0.0336(10) 0.0319(10) 0.0246(9) 0.0014(8) -0.0003(7) 0.0025(8) C8 0.0360(10) 0.0369(11) 0.0303(10) -0.0018(8) 0.0057(8) 0.0045(9) C9 0.0299(10) 0.0305(10) 0.0425(11) -0.0034(9) 0.0034(8) 0.0039(9) C10 0.0306(10) 0.0328(11) 0.0367(11) 0.0044(8) -0.0045(8) 0.0018(9) C11 0.0303(10) 0.0343(10) 0.0270(9) 0.0006(8) -0.0024(7) -0.0025(8) C12 0.0222(9) 0.0281(10) 0.0303(9) -0.0035(7) -0.0002(7) -0.0028(8) C13 0.0320(10) 0.0298(10) 0.0312(10) -0.0045(8) -0.0005(8) 0.0035(8) C14 0.0349(10) 0.0316(10) 0.0313(10) -0.0019(8) -0.0038(8) -0.0019(9) C15 0.0247(9) 0.0283(10) 0.0465(12) -0.0007(9) -0.0048(8) -0.0044(8) C16 0.0260(10) 0.0351(11) 0.0508(13) -0.0019(9) 0.0070(9) 0.0051(9) C17 0.0285(10) 0.0342(11) 0.0375(10) -0.0001(8) 0.0066(8) 0.0009(9) C18 0.0336(10) 0.0348(11) 0.0582(13) 0.0065(10) -0.0075(9) 0.0006(10) C19 0.0297(9) 0.0307(10) 0.0290(10) -0.0031(8) 0.0021(8) -0.0039(8) C20 0.0317(10) 0.0331(10) 0.0288(10) -0.0026(8) 0.0033(8) -0.0040(9) C21 0.0258(9) 0.0311(10) 0.0268(9) -0.0056(8) 0.0039(7) -0.0067(8) C22 0.0253(9) 0.0321(10) 0.0352(10) -0.0014(8) 0.0008(7) -0.0015(8) C23 0.0298(10) 0.0403(11) 0.0268(9) 0.0012(8) 0.0046(7) -0.0035(9) C24 0.0292(10) 0.0384(11) 0.0321(10) -0.0084(8) 0.0063(8) -0.0027(9) C25 0.0332(10) 0.0315(10) 0.0371(11) -0.0047(9) 0.0010(8) 0.0016(9) C26 0.0358(10) 0.0323(10) 0.0269(10) -0.0011(8) 0.0014(8) -0.0039(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 F1 C3 1.3448(19) . ? O1 C5 1.371(2) . ? O1 C2 1.378(2) . ? C2 C3 1.351(2) . ? C2 C6 1.450(2) . ? C3 C4 1.415(3) . ? C4 C5 1.379(2) . ? C4 C19 1.423(2) . ? C5 C12 1.454(2) . ? C6 C7 1.393(2) . ? C6 C11 1.399(2) . ? C7 C8 1.382(3) . ? C7 H7 0.9500 . ? C8 C9 1.384(3) . ? C8 H8 0.9500 . ? C9 C10 1.383(3) . ? C9 H9 0.9500 . ? C10 C11 1.381(3) . ? C10 H10 0.9500 . ? C11 H11 0.9500 . ? C12 C17 1.390(2) . ? C12 C13 1.394(3) . ? C13 C14 1.382(3) . ? C13 H13 0.9500 . ? C14 C15 1.388(3) . ? C14 H14 0.9500 . ? C15 C16 1.393(3) . ? C15 C18 1.508(3) . ? C16 C17 1.385(3) . ? C16 H16 0.9500 . ? C17 H17 0.9500 . ? C18 H18A 0.9800 . ? C18 H18B 0.9800 . ? C18 H18C 0.9800 . ? C19 C20 1.198(2) . ? C20 C21 1.436(2) . ? C21 C26 1.394(3) . ? C21 C22 1.399(3) . ? C22 C23 1.384(3) . ? C22 H22 0.9500 . ? C23 C24 1.378(3) . ? C23 H23 0.9500 . ? C24 C25 1.384(3) . ? C24 H24 0.9500 . ? C25 C26 1.385(3) . ? C25 H25 0.9500 . ? C26 H26 0.9500 . ? 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 C5 O1 C2 108.52(13) . . ? C3 C2 O1 107.18(14) . . ? C3 C2 C6 134.73(16) . . ? O1 C2 C6 118.09(14) . . ? F1 C3 C2 125.96(16) . . ? F1 C3 C4 123.91(15) . . ? C2 C3 C4 110.13(15) . . ? C5 C4 C3 104.71(15) . . ? C5 C4 C19 129.38(17) . . ? C3 C4 C19 125.91(16) . . ? O1 C5 C4 109.46(15) . . ? O1 C5 C12 116.19(14) . . ? C4 C5 C12 134.35(16) . . ? C7 C6 C11 118.62(16) . . ? C7 C6 C2 121.45(15) . . ? C11 C6 C2 119.93(15) . . ? C8 C7 C6 120.46(17) . . ? C8 C7 H7 119.8 . . ? C6 C7 H7 119.8 . . ? C7 C8 C9 120.56(17) . . ? C7 C8 H8 119.7 . . ? C9 C8 H8 119.7 . . ? C10 C9 C8 119.39(17) . . ? C10 C9 H9 120.3 . . ? C8 C9 H9 120.3 . . ? C11 C10 C9 120.55(17) . . ? C11 C10 H10 119.7 . . ? C9 C10 H10 119.7 . . ? C10 C11 C6 120.41(17) . . ? C10 C11 H11 119.8 . . ? C6 C11 H11 119.8 . . ? C17 C12 C13 117.89(16) . . ? C17 C12 C5 121.42(16) . . ? C13 C12 C5 120.68(16) . . ? C14 C13 C12 120.69(17) . . ? C14 C13 H13 119.7 . . ? C12 C13 H13 119.7 . . ? C13 C14 C15 121.81(18) . . ? C13 C14 H14 119.1 . . ? C15 C14 H14 119.1 . . ? C14 C15 C16 117.25(17) . . ? C14 C15 C18 121.53(18) . . ? C16 C15 C18 121.21(18) . . ? C17 C16 C15 121.40(18) . . ? C17 C16 H16 119.3 . . ? C15 C16 H16 119.3 . . ? C16 C17 C12 120.95(17) . . ? C16 C17 H17 119.5 . . ? C12 C17 H17 119.5 . . ? C15 C18 H18A 109.5 . . ? C15 C18 H18B 109.5 . . ? H18A C18 H18B 109.5 . . ? C15 C18 H18C 109.5 . . ? H18A C18 H18C 109.5 . . ? H18B C18 H18C 109.5 . . ? C20 C19 C4 177.8(2) . . ? C19 C20 C21 178.0(2) . . ? C26 C21 C22 119.05(16) . . ? C26 C21 C20 120.44(16) . . ? C22 C21 C20 120.51(17) . . ? C23 C22 C21 119.94(17) . . ? C23 C22 H22 120.0 . . ? C21 C22 H22 120.0 . . ? C24 C23 C22 120.55(17) . . ? C24 C23 H23 119.7 . . ? C22 C23 H23 119.7 . . ? C23 C24 C25 120.03(17) . . ? C23 C24 H24 120.0 . . ? C25 C24 H24 120.0 . . ? C24 C25 C26 120.02(18) . . ? C24 C25 H25 120.0 . . ? C26 C25 H25 120.0 . . ? C25 C26 C21 120.40(17) . . ? C25 C26 H26 119.8 . . ? C21 C26 H26 119.8 . . ? 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 C5 O1 C2 C3 -0.27(18) . . . . ? C5 O1 C2 C6 -179.49(14) . . . . ? O1 C2 C3 F1 -179.51(15) . . . . ? C6 C2 C3 F1 -0.5(3) . . . . ? O1 C2 C3 C4 0.40(19) . . . . ? C6 C2 C3 C4 179.43(18) . . . . ? F1 C3 C4 C5 179.54(16) . . . . ? C2 C3 C4 C5 -0.4(2) . . . . ? F1 C3 C4 C19 -1.1(3) . . . . ? C2 C3 C4 C19 178.98(17) . . . . ? C2 O1 C5 C4 0.04(18) . . . . ? C2 O1 C5 C12 -179.94(14) . . . . ? C3 C4 C5 O1 0.20(19) . . . . ? C19 C4 C5 O1 -179.13(17) . . . . ? C3 C4 C5 C12 -179.83(19) . . . . ? C19 C4 C5 C12 0.8(3) . . . . ? C3 C2 C6 C7 -176.98(19) . . . . ? O1 C2 C6 C7 2.0(2) . . . . ? C3 C2 C6 C11 2.2(3) . . . . ? O1 C2 C6 C11 -178.84(15) . . . . ? C11 C6 C7 C8 -1.3(3) . . . . ? C2 C6 C7 C8 177.91(17) . . . . ? C6 C7 C8 C9 1.0(3) . . . . ? C7 C8 C9 C10 -0.2(3) . . . . ? C8 C9 C10 C11 -0.4(3) . . . . ? C9 C10 C11 C6 0.1(3) . . . . ? C7 C6 C11 C10 0.7(3) . . . . ? C2 C6 C11 C10 -178.47(16) . . . . ? O1 C5 C12 C17 -176.85(15) . . . . ? C4 C5 C12 C17 3.2(3) . . . . ? O1 C5 C12 C13 3.9(2) . . . . ? C4 C5 C12 C13 -176.02(19) . . . . ? C17 C12 C13 C14 1.0(3) . . . . ? C5 C12 C13 C14 -179.75(16) . . . . ? C12 C13 C14 C15 -0.8(3) . . . . ? C13 C14 C15 C16 0.0(3) . . . . ? C13 C14 C15 C18 179.72(17) . . . . ? C14 C15 C16 C17 0.5(3) . . . . ? C18 C15 C16 C17 -179.25(17) . . . . ? C15 C16 C17 C12 -0.2(3) . . . . ? C13 C12 C17 C16 -0.5(3) . . . . ? C5 C12 C17 C16 -179.78(17) . . . . ? C5 C4 C19 C20 165(5) . . . . ? C3 C4 C19 C20 -14(5) . . . . ? C4 C19 C20 C21 177(100) . . . . ? C19 C20 C21 C26 22(6) . . . . ? C19 C20 C21 C22 -158(6) . . . . ? C26 C21 C22 C23 -0.6(3) . . . . ? C20 C21 C22 C23 178.95(17) . . . . ? C21 C22 C23 C24 0.2(3) . . . . ? C22 C23 C24 C25 0.0(3) . . . . ? C23 C24 C25 C26 0.3(3) . . . . ? C24 C25 C26 C21 -0.8(3) . . . . ? C22 C21 C26 C25 0.9(3) . . . . ? C20 C21 C26 C25 -178.64(17) . . . . ? _diffrn_measured_fraction_theta_max 0.993 _diffrn_reflns_theta_full 67.59 _diffrn_measured_fraction_theta_full 0.993 _refine_diff_density_max 0.186 _refine_diff_density_min -0.161 _refine_diff_density_rms 0.036 #===END