# 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_orth_p212121 _database_code_depnum_ccdc_archive 'CCDC 914474' #TrackingRef '15927_web_deposit_cif_file_0_YoichiHabata_1354751754.orth_p212121.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C15 H18 F6 N P' _chemical_formula_weight 357.27 _chemical_absolute_configuration rm 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' F F 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' P P 0.1023 0.0942 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Orthorhombic _symmetry_space_group_name_H-M P2(1)2(1)2(1) loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, -y, z+1/2' '-x, y+1/2, -z+1/2' 'x+1/2, -y+1/2, -z' _cell_length_a 8.7662(6) _cell_length_b 11.1969(7) _cell_length_c 16.9395(12) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 1662.68(19) _cell_formula_units_Z 4 _cell_measurement_temperature 173 _cell_measurement_reflns_used 1354 _cell_measurement_theta_min 2.18 _cell_measurement_theta_max 21.55 _exptl_crystal_description block _exptl_crystal_colour colourless _exptl_crystal_size_max 0.21 _exptl_crystal_size_mid 0.18 _exptl_crystal_size_min 0.09 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.427 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 736 _exptl_absorpt_coefficient_mu 0.222 _exptl_absorpt_correction_type empirical _exptl_absorpt_correction_T_min 0.9557 _exptl_absorpt_correction_T_max 0.9799 _exptl_absorpt_process_details 'SADABS; Sheldrick 1996' _exptl_special_details ; ? ; _diffrn_ambient_temperature 173 _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 'CCD area detector' _diffrn_measurement_method 'phi and omega scans' _diffrn_detector_area_resol_mean 8.333 _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 8693 _diffrn_reflns_av_R_equivalents 0.0425 _diffrn_reflns_av_sigmaI/netI 0.0472 _diffrn_reflns_limit_h_min -9 _diffrn_reflns_limit_h_max 10 _diffrn_reflns_limit_k_min -13 _diffrn_reflns_limit_k_max 13 _diffrn_reflns_limit_l_min -16 _diffrn_reflns_limit_l_max 20 _diffrn_reflns_theta_min 2.18 _diffrn_reflns_theta_max 24.81 _reflns_number_total 2864 _reflns_number_gt 2114 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'Bruker SMART' _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^)+(0.0828P)^2^+0.4809P] 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_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881' _refine_ls_abs_structure_Flack -0.1(2) _refine_ls_number_reflns 2864 _refine_ls_number_parameters 280 _refine_ls_number_restraints 36 _refine_ls_R_factor_all 0.0757 _refine_ls_R_factor_gt 0.0508 _refine_ls_wR_factor_ref 0.1501 _refine_ls_wR_factor_gt 0.1305 _refine_ls_goodness_of_fit_ref 1.017 _refine_ls_restrained_S_all 1.190 _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 P1 P 0.07104(16) 0.94368(12) 0.44110(8) 0.0468(4) Uani 1 1 d . . . F1 F -0.0617(4) 0.8492(3) 0.4618(2) 0.0710(10) Uani 1 1 d U . . F2 F 0.1932(4) 0.8411(3) 0.4596(2) 0.0658(10) Uani 1 1 d U . . C8 C -0.0688(7) 0.8347(4) 0.7179(3) 0.0455(13) Uani 1 1 d . . . N1 N 0.2482(5) 0.8056(4) 0.6352(3) 0.0376(10) Uani 1 1 d . . . C6 C -0.1325(7) 0.8387(5) 0.8552(4) 0.0517(14) Uani 1 1 d . . . C10 C 0.4420(5) 0.9618(4) 0.6566(3) 0.0394(11) Uani 1 1 d . . . F6 F 0.0733(5) 0.9738(3) 0.5339(2) 0.0779(11) Uani 1 1 d U . . C2 C 0.0604(7) 0.6482(5) 0.6007(3) 0.0442(12) Uani 1 1 d . . . F3 F 0.1980(5) 1.0343(4) 0.4205(3) 0.1122(16) Uani 1 1 d U . . C11 C 0.5740(6) 0.9381(5) 0.6148(3) 0.0468(12) Uani 1 1 d . . . C1 C 0.1479(5) 0.7062(4) 0.6674(3) 0.0360(11) Uani 1 1 d . . . C7 C -0.1579(6) 0.8775(5) 0.7789(4) 0.0514(14) Uani 1 1 d . . . C4 C 0.0701(7) 0.7143(5) 0.8096(3) 0.0474(12) Uani 1 1 d . . . C9 C 0.3528(6) 0.8627(5) 0.6949(3) 0.0455(13) Uani 1 1 d . . . F4 F -0.0550(5) 1.0426(4) 0.4311(3) 0.0945(13) Uani 1 1 d U . . C12 C 0.6543(6) 1.0289(5) 0.5784(3) 0.0507(14) Uani 1 1 d . . . C3 C 0.0476(5) 0.7537(4) 0.7325(3) 0.0351(11) Uani 1 1 d . . . C13 C 0.6019(7) 1.1447(5) 0.5836(3) 0.0503(14) Uani 1 1 d . . . F5 F 0.0615(8) 0.9017(5) 0.3535(3) 0.1373(18) Uani 1 1 d U . . C14 C 0.4727(7) 1.1699(6) 0.6248(4) 0.0612(17) Uani 1 1 d . . . C15 C 0.3921(6) 1.0800(5) 0.6611(3) 0.0508(14) Uani 1 1 d . . . C5 C -0.0191(7) 0.7584(6) 0.8700(4) 0.0598(17) Uani 1 1 d . . . H10 H 0.223(4) 0.649(3) 0.689(2) 0.017(9) Uiso 1 1 d . . . H4 H -0.234(6) 0.926(4) 0.770(3) 0.044(14) Uiso 1 1 d . . . H3 H 0.001(6) 0.697(5) 0.583(3) 0.045(17) Uiso 1 1 d . . . H14 H 0.737(7) 1.011(5) 0.546(3) 0.056(17) Uiso 1 1 d . . . H9 H 0.432(6) 0.782(5) 0.711(3) 0.066(15) Uiso 1 1 d . . . H13 H 0.621(6) 0.851(5) 0.612(3) 0.056(16) Uiso 1 1 d . . . H15 H 0.447(7) 1.256(5) 0.631(3) 0.069(18) Uiso 1 1 d . . . H2 H 0.130(6) 0.605(5) 0.564(3) 0.061(17) Uiso 1 1 d . . . H12 H 0.313(6) 1.094(4) 0.690(3) 0.047(16) Uiso 1 1 d . . . H5 H -0.184(7) 0.873(5) 0.891(3) 0.055(17) Uiso 1 1 d . . . H16 H 0.651(9) 1.200(7) 0.564(4) 0.10(3) Uiso 1 1 d . . . H6 H -0.017(7) 0.732(6) 0.926(4) 0.08(2) Uiso 1 1 d . . . H8 H 0.294(5) 0.894(4) 0.732(3) 0.037(14) Uiso 1 1 d . . . H1 H 0.007(6) 0.570(5) 0.615(3) 0.062(16) Uiso 1 1 d . . . H7 H 0.136(7) 0.659(5) 0.817(4) 0.067(19) Uiso 1 1 d . . . H11 H -0.080(7) 0.850(4) 0.673(3) 0.050(16) Uiso 1 1 d . . . H18 H 0.185(7) 0.866(5) 0.614(4) 0.067(18) Uiso 1 1 d . . . H17 H 0.296(8) 0.784(6) 0.599(4) 0.08(2) Uiso 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 P1 0.0377(7) 0.0493(7) 0.0532(8) 0.0077(6) -0.0022(7) 0.0026(7) F1 0.0516(17) 0.0656(19) 0.096(3) 0.0066(18) -0.0114(19) -0.0126(17) F2 0.0499(17) 0.065(2) 0.082(2) 0.0071(18) 0.0090(16) 0.0158(16) C8 0.050(3) 0.043(3) 0.043(3) 0.006(2) 0.000(3) 0.016(3) N1 0.033(2) 0.045(2) 0.035(2) 0.0010(19) 0.002(2) 0.0010(19) C6 0.049(3) 0.056(3) 0.051(4) -0.018(3) 0.012(3) -0.008(3) C10 0.035(2) 0.047(3) 0.036(3) -0.002(2) -0.005(2) -0.003(3) F6 0.093(2) 0.0720(19) 0.069(2) -0.0143(16) -0.015(2) 0.015(2) C2 0.047(3) 0.042(3) 0.044(3) -0.005(2) -0.002(3) 0.004(3) F3 0.076(2) 0.082(2) 0.178(4) 0.040(3) 0.033(3) -0.014(2) C11 0.043(3) 0.048(3) 0.050(3) -0.010(2) 0.000(3) -0.005(3) C1 0.034(2) 0.039(2) 0.035(3) 0.005(2) 0.002(2) 0.007(2) C7 0.043(3) 0.042(3) 0.069(4) -0.006(3) 0.007(3) 0.010(3) C4 0.044(3) 0.056(3) 0.042(3) 0.006(2) 0.003(3) 0.006(3) C9 0.041(3) 0.059(3) 0.036(3) -0.002(3) -0.005(2) -0.004(3) F4 0.071(2) 0.080(2) 0.132(3) 0.045(2) 0.000(2) 0.027(2) C12 0.038(3) 0.065(4) 0.049(3) -0.014(3) 0.001(3) -0.012(3) C3 0.028(2) 0.038(2) 0.039(2) -0.0015(19) 0.003(2) 0.001(2) C13 0.053(4) 0.055(3) 0.043(3) 0.006(3) -0.007(3) -0.011(3) F5 0.180(4) 0.175(4) 0.056(2) 0.005(2) 0.004(3) 0.017(4) C14 0.051(4) 0.055(4) 0.077(4) 0.006(3) -0.007(3) 0.002(3) C15 0.037(3) 0.061(4) 0.054(3) 0.001(3) 0.003(3) 0.010(3) C5 0.059(4) 0.080(4) 0.041(3) -0.004(3) 0.008(3) -0.005(3) _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 P1 F3 1.546(4) . ? P1 F5 1.559(5) . ? P1 F4 1.573(4) . ? P1 F2 1.601(3) . ? P1 F6 1.609(4) . ? P1 F1 1.611(3) . ? C8 C7 1.381(8) . ? C8 C3 1.388(7) . ? C8 H11 0.79(6) . ? N1 C9 1.507(7) . ? N1 C1 1.520(6) . ? N1 H18 0.95(6) . ? N1 H17 0.78(7) . ? C6 C5 1.364(8) . ? C6 C7 1.382(9) . ? C6 H5 0.85(6) . ? C10 C11 1.382(7) . ? C10 C15 1.397(7) . ? C10 C9 1.504(7) . ? C2 C1 1.513(7) . ? C2 H3 0.81(5) . ? C2 H2 1.00(6) . ? C2 H1 1.02(6) . ? C11 C12 1.382(8) . ? C11 H13 1.06(5) . ? C1 C3 1.507(6) . ? C1 H10 0.99(4) . ? C7 H4 0.87(5) . ? C4 C5 1.379(8) . ? C4 C3 1.392(7) . ? C4 H7 0.86(6) . ? C9 H9 1.17(6) . ? C9 H8 0.89(5) . ? C12 C13 1.379(8) . ? C12 H14 0.93(6) . ? C13 C14 1.359(8) . ? C13 H16 0.83(7) . ? C14 C15 1.375(8) . ? C14 H15 0.99(5) . ? C15 H12 0.86(6) . ? C5 H6 0.99(7) . ? 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 F3 P1 F5 91.3(3) . . ? F3 P1 F4 91.1(2) . . ? F5 P1 F4 94.1(3) . . ? F3 P1 F2 91.9(2) . . ? F5 P1 F2 90.3(3) . . ? F4 P1 F2 174.6(2) . . ? F3 P1 F6 94.2(3) . . ? F5 P1 F6 174.0(3) . . ? F4 P1 F6 88.1(2) . . ? F2 P1 F6 87.21(19) . . ? F3 P1 F1 179.5(3) . . ? F5 P1 F1 88.3(3) . . ? F4 P1 F1 88.8(2) . . ? F2 P1 F1 88.25(17) . . ? F6 P1 F1 86.2(2) . . ? C7 C8 C3 120.6(5) . . ? C7 C8 H11 125(4) . . ? C3 C8 H11 114(4) . . ? C9 N1 C1 115.0(4) . . ? C9 N1 H18 108(4) . . ? C1 N1 H18 109(4) . . ? C9 N1 H17 109(5) . . ? C1 N1 H17 111(5) . . ? H18 N1 H17 104(6) . . ? C5 C6 C7 119.8(6) . . ? C5 C6 H5 123(4) . . ? C7 C6 H5 117(4) . . ? C11 C10 C15 118.2(5) . . ? C11 C10 C9 121.0(5) . . ? C15 C10 C9 120.8(5) . . ? C1 C2 H3 108(4) . . ? C1 C2 H2 112(3) . . ? H3 C2 H2 119(5) . . ? C1 C2 H1 115(3) . . ? H3 C2 H1 111(5) . . ? H2 C2 H1 90(4) . . ? C12 C11 C10 120.9(5) . . ? C12 C11 H13 117(3) . . ? C10 C11 H13 122(3) . . ? C3 C1 C2 113.7(4) . . ? C3 C1 N1 110.0(4) . . ? C2 C1 N1 109.8(4) . . ? C3 C1 H10 110(2) . . ? C2 C1 H10 110(2) . . ? N1 C1 H10 103(2) . . ? C8 C7 C6 120.0(5) . . ? C8 C7 H4 121(3) . . ? C6 C7 H4 119(3) . . ? C5 C4 C3 120.2(5) . . ? C5 C4 H7 123(4) . . ? C3 C4 H7 117(4) . . ? C10 C9 N1 109.9(4) . . ? C10 C9 H9 111(3) . . ? N1 C9 H9 101(3) . . ? C10 C9 H8 109(3) . . ? N1 C9 H8 107(3) . . ? H9 C9 H8 118(4) . . ? C13 C12 C11 119.6(5) . . ? C13 C12 H14 120(3) . . ? C11 C12 H14 120(3) . . ? C8 C3 C4 118.6(5) . . ? C8 C3 C1 121.9(4) . . ? C4 C3 C1 119.5(4) . . ? C14 C13 C12 120.4(6) . . ? C14 C13 H16 119(5) . . ? C12 C13 H16 120(5) . . ? C13 C14 C15 120.4(6) . . ? C13 C14 H15 116(4) . . ? C15 C14 H15 123(4) . . ? C14 C15 C10 120.5(5) . . ? C14 C15 H12 122(3) . . ? C10 C15 H12 117(3) . . ? C6 C5 C4 120.8(6) . . ? C6 C5 H6 113(4) . . ? C4 C5 H6 126(4) . . ? _diffrn_measured_fraction_theta_max 1.000 _diffrn_reflns_theta_full 24.81 _diffrn_measured_fraction_theta_full 1.000 _refine_diff_density_max 0.438 _refine_diff_density_min -0.240 _refine_diff_density_rms 0.051