# Electronic Supplementary Material (ESI) for Chemical Science # This journal is © The Royal Society of Chemistry 2012 ####################################################################### # # 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_ltp230s _database_code_depnum_ccdc_archive 'CCDC 881754' #TrackingRef '- ltp230s.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C12 H9 F3 N2 O' _chemical_formula_sum 'C12 H9 F3 N2 O' _chemical_formula_weight 254.21 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' _symmetry_cell_setting Monoclinic _symmetry_space_group_name_H-M P2(1)/n loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, y+1/2, -z+1/2' '-x, -y, -z' 'x-1/2, -y-1/2, z-1/2' _cell_length_a 6.2648(2) _cell_length_b 8.9839(3) _cell_length_c 20.5622(5) _cell_angle_alpha 90.00 _cell_angle_beta 95.4600(10) _cell_angle_gamma 90.00 _cell_volume 1152.04(6) _cell_formula_units_Z 4 _cell_measurement_temperature 103(2) _cell_measurement_reflns_used 3207 _cell_measurement_theta_min 3.02 _cell_measurement_theta_max 29.61 _exptl_crystal_description plate _exptl_crystal_colour colourless _exptl_crystal_size_max 0.40 _exptl_crystal_size_mid 0.38 _exptl_crystal_size_min 0.10 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.466 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 520 _exptl_absorpt_coefficient_mu 0.128 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.9504 _exptl_absorpt_correction_T_max 0.9873 _exptl_absorpt_process_details sadabs _exptl_special_details ; ? ; _diffrn_ambient_temperature 103(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 ? _diffrn_reflns_number 9979 _diffrn_reflns_av_R_equivalents 0.0299 _diffrn_reflns_av_sigmaI/netI 0.0346 _diffrn_reflns_limit_h_min -6 _diffrn_reflns_limit_h_max 8 _diffrn_reflns_limit_k_min -12 _diffrn_reflns_limit_k_max 12 _diffrn_reflns_limit_l_min -28 _diffrn_reflns_limit_l_max 28 _diffrn_reflns_theta_min 1.99 _diffrn_reflns_theta_max 29.64 _reflns_number_total 3206 _reflns_number_gt 2565 _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^)+(0.0772P)^2^+0.3540P] 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 3206 _refine_ls_number_parameters 164 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0588 _refine_ls_R_factor_gt 0.0454 _refine_ls_wR_factor_ref 0.1427 _refine_ls_wR_factor_gt 0.1258 _refine_ls_goodness_of_fit_ref 1.088 _refine_ls_restrained_S_all 1.088 _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 C1 C 0.2335(2) 0.39184(18) 0.50488(7) 0.0204(3) Uani 1 1 d . . . C2 C 0.1971(2) 0.26999(17) 0.45906(7) 0.0170(3) Uani 1 1 d . . . C3 C 0.3519(2) 0.23627(18) 0.41714(7) 0.0183(3) Uani 1 1 d . . . H3 H 0.4829 0.2902 0.4194 0.022 Uiso 1 1 calc R . . C4 C 0.3119(2) 0.12253(17) 0.37190(7) 0.0160(3) Uani 1 1 d . . . H4 H 0.4169 0.0979 0.3432 0.019 Uiso 1 1 calc R . . C5 C 0.1197(2) 0.04446(16) 0.36818(6) 0.0129(3) Uani 1 1 d . . . C6 C -0.0345(2) 0.07951(17) 0.41052(6) 0.0156(3) Uani 1 1 d . . . H6 H -0.1663 0.0266 0.4078 0.019 Uiso 1 1 calc R . . C7 C 0.0046(2) 0.19126(17) 0.45643(7) 0.0174(3) Uani 1 1 d . . . H7 H -0.0987 0.2141 0.4859 0.021 Uiso 1 1 calc R . . C8 C 0.0742(2) -0.07143(16) 0.31670(6) 0.0130(3) Uani 1 1 d . . . C9 C -0.2167(2) -0.12712(16) 0.22932(6) 0.0141(3) Uani 1 1 d . . . C10 C -0.4101(2) -0.05861(18) 0.19257(7) 0.0202(3) Uani 1 1 d . . . H10A H -0.4505 -0.1166 0.1529 0.030 Uiso 1 1 calc R . . H10B H -0.3771 0.0438 0.1805 0.030 Uiso 1 1 calc R . . H10C H -0.5292 -0.0582 0.2202 0.030 Uiso 1 1 calc R . . C11 C 0.1903(2) -0.19499(17) 0.31136(7) 0.0162(3) Uani 1 1 d . . . H11 H 0.1581 -0.2544 0.2735 0.019 Uiso 1 1 calc R . . C12 C 0.3654(2) -0.24708(17) 0.35966(7) 0.0177(3) Uani 1 1 d . . . F1 F 0.34693(16) -0.20723(13) 0.42141(4) 0.0292(3) Uani 1 1 d . . . F2 F 0.56102(16) -0.19954(15) 0.34693(5) 0.0346(3) Uani 1 1 d . . . F3 F 0.37573(19) -0.39568(12) 0.35864(6) 0.0387(3) Uani 1 1 d . . . N1 N 0.2606(2) 0.48905(18) 0.54043(7) 0.0274(3) Uani 1 1 d . . . N2 N -0.10356(19) -0.03474(13) 0.27300(5) 0.0139(3) Uani 1 1 d . . . H2 H -0.1475 0.0582 0.2737 0.017 Uiso 1 1 calc R . . O1 O -0.16531(17) -0.25693(12) 0.22118(5) 0.0172(2) Uani 1 1 d . . . 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 C1 0.0191(7) 0.0195(8) 0.0214(7) -0.0040(6) -0.0041(5) 0.0034(6) C2 0.0204(7) 0.0138(7) 0.0156(6) -0.0023(5) -0.0042(5) 0.0028(6) C3 0.0150(7) 0.0162(7) 0.0229(7) -0.0018(6) -0.0028(5) -0.0018(6) C4 0.0151(7) 0.0145(7) 0.0184(6) -0.0014(5) 0.0021(5) -0.0005(5) C5 0.0151(6) 0.0101(6) 0.0130(6) 0.0003(5) -0.0007(5) 0.0000(5) C6 0.0156(7) 0.0142(7) 0.0171(6) 0.0012(5) 0.0017(5) -0.0006(5) C7 0.0190(7) 0.0179(7) 0.0154(6) 0.0000(5) 0.0026(5) 0.0022(6) C8 0.0133(6) 0.0121(6) 0.0134(5) 0.0011(5) 0.0011(5) -0.0028(5) C9 0.0171(7) 0.0117(6) 0.0135(5) 0.0000(5) 0.0017(5) -0.0015(5) C10 0.0221(7) 0.0155(7) 0.0214(7) -0.0031(6) -0.0062(5) 0.0026(6) C11 0.0156(7) 0.0141(7) 0.0186(6) -0.0018(5) -0.0001(5) -0.0003(5) C12 0.0167(7) 0.0151(7) 0.0212(7) -0.0005(5) 0.0015(5) 0.0016(6) F1 0.0316(6) 0.0372(6) 0.0184(4) 0.0025(4) 0.0003(4) 0.0145(5) F2 0.0150(5) 0.0541(8) 0.0343(5) 0.0132(5) 0.0008(4) -0.0010(5) F3 0.0413(6) 0.0151(5) 0.0548(7) -0.0016(5) -0.0208(5) 0.0083(5) N1 0.0243(7) 0.0260(8) 0.0302(7) -0.0105(6) -0.0063(5) 0.0046(6) N2 0.0165(6) 0.0081(5) 0.0167(5) -0.0007(4) -0.0016(4) 0.0006(4) O1 0.0195(5) 0.0110(5) 0.0209(5) -0.0034(4) 0.0002(4) -0.0003(4) _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 C1 N1 1.141(2) . ? C1 C2 1.448(2) . ? C2 C3 1.391(2) . ? C2 C7 1.395(2) . ? C3 C4 1.388(2) . ? C3 H3 0.9500 . ? C4 C5 1.390(2) . ? C4 H4 0.9500 . ? C5 C6 1.3962(19) . ? C5 C8 1.4927(18) . ? C6 C7 1.384(2) . ? C6 H6 0.9500 . ? C7 H7 0.9500 . ? C8 C11 1.338(2) . ? C8 N2 1.4020(17) . ? C9 O1 1.2255(18) . ? C9 N2 1.3699(18) . ? C9 C10 1.498(2) . ? C10 H10A 0.9800 . ? C10 H10B 0.9800 . ? C10 H10C 0.9800 . ? C11 C12 1.483(2) . ? C11 H11 0.9500 . ? C12 F1 1.3348(17) . ? C12 F3 1.3368(18) . ? C12 F2 1.3469(18) . ? N2 H2 0.8800 . ? 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 N1 C1 C2 179.10(18) . . ? C3 C2 C7 121.12(13) . . ? C3 C2 C1 119.49(14) . . ? C7 C2 C1 119.36(13) . . ? C4 C3 C2 118.92(14) . . ? C4 C3 H3 120.5 . . ? C2 C3 H3 120.5 . . ? C3 C4 C5 120.56(13) . . ? C3 C4 H4 119.7 . . ? C5 C4 H4 119.7 . . ? C4 C5 C6 119.94(13) . . ? C4 C5 C8 119.80(12) . . ? C6 C5 C8 120.18(12) . . ? C7 C6 C5 120.06(13) . . ? C7 C6 H6 120.0 . . ? C5 C6 H6 120.0 . . ? C6 C7 C2 119.38(13) . . ? C6 C7 H7 120.3 . . ? C2 C7 H7 120.3 . . ? C11 C8 N2 123.20(13) . . ? C11 C8 C5 124.64(12) . . ? N2 C8 C5 112.14(12) . . ? O1 C9 N2 122.68(13) . . ? O1 C9 C10 122.17(13) . . ? N2 C9 C10 115.15(13) . . ? C9 C10 H10A 109.5 . . ? C9 C10 H10B 109.5 . . ? H10A C10 H10B 109.5 . . ? C9 C10 H10C 109.5 . . ? H10A C10 H10C 109.5 . . ? H10B C10 H10C 109.5 . . ? C8 C11 C12 125.46(13) . . ? C8 C11 H11 117.3 . . ? C12 C11 H11 117.3 . . ? F1 C12 F3 106.95(13) . . ? F1 C12 F2 105.23(12) . . ? F3 C12 F2 105.50(13) . . ? F1 C12 C11 115.27(12) . . ? F3 C12 C11 109.77(12) . . ? F2 C12 C11 113.46(12) . . ? C9 N2 C8 127.41(13) . . ? C9 N2 H2 116.3 . . ? C8 N2 H2 116.3 . . ? _diffrn_measured_fraction_theta_max 0.982 _diffrn_reflns_theta_full 29.64 _diffrn_measured_fraction_theta_full 0.982 _refine_diff_density_max 0.436 _refine_diff_density_min -0.477 _refine_diff_density_rms 0.107