# 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_8415 _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C15 H6 F4 N4 O' _chemical_formula_weight 334.24 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 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 6.1396(12) _cell_length_b 7.5599(15) _cell_length_c 30.535(6) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 1417.3(5) _cell_formula_units_Z 4 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used 11630 _cell_measurement_theta_min 2.67 _cell_measurement_theta_max 27.47 _exptl_crystal_description block _exptl_crystal_colour colorless _exptl_crystal_size_max 0.80 _exptl_crystal_size_mid 0.40 _exptl_crystal_size_min 0.10 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.566 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 672 _exptl_absorpt_coefficient_mu 0.139 _exptl_absorpt_correction_type Empirical _exptl_absorpt_correction_T_min 0.8968 _exptl_absorpt_correction_T_max 0.9862 _exptl_absorpt_process_details ; HIGASHI, T. (1995). Abscor-Empirical Absorption Correction based on Fourier Series Approximation. Rigaku Corporation,Tokyo,Japan. ; _diffrn_ambient_temperature 293(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 'Rigaku RAXIS RAPID IP' _diffrn_measurement_method \W _diffrn_detector_area_resol_mean 10.00 _diffrn_standards_number 0 _diffrn_standards_interval_count 0 _diffrn_standards_interval_time 0 _diffrn_standards_decay_% 0 _diffrn_reflns_number 11630 _diffrn_reflns_av_R_equivalents 0.04723670 _diffrn_reflns_av_sigmaI/netI 0.0855 _diffrn_reflns_limit_h_min -7 _diffrn_reflns_limit_h_max 7 _diffrn_reflns_limit_k_min -9 _diffrn_reflns_limit_k_max 9 _diffrn_reflns_limit_l_min -39 _diffrn_reflns_limit_l_max 39 _diffrn_reflns_theta_min 2.67 _diffrn_reflns_theta_max 27.47 _reflns_number_total 1905 _reflns_number_gt 845 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Rapid-AUTO (Rigaku,2000)' _computing_cell_refinement Rapid-AUTO _computing_data_reduction 'CrystalStructure (Rigaku/MSC,2000)' _computing_structure_solution SHELXS-97,(Sheldrick,1997) _computing_structure_refinement SHELXL-97,(Sheldrick,1997) _computing_molecular_graphics 'Siemens SHELXTL V4.2,(Sheldrick,1990)' _computing_publication_material SHELXL-97,(Sheldrick,1997) _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^)+(0.0120P)^2^+0.0000P] 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 none _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 4.2(17) _refine_ls_number_reflns 1905 _refine_ls_number_parameters 217 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.1025 _refine_ls_R_factor_gt 0.0386 _refine_ls_wR_factor_ref 0.0701 _refine_ls_wR_factor_gt 0.0616 _refine_ls_goodness_of_fit_ref 0.970 _refine_ls_restrained_S_all 0.970 _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 0.5891(6) 0.4542(5) 0.24878(11) 0.0468(10) Uani 1 1 d . . . C2 C 0.6114(6) 0.4204(5) 0.20074(11) 0.0443(10) Uani 1 1 d . . . C3 C 0.7983(6) 0.3504(6) 0.18357(13) 0.0511(11) Uani 1 1 d . . . C4 C 0.8372(6) 0.3353(6) 0.13910(14) 0.0528(11) Uani 1 1 d . . . C5 C 0.6871(7) 0.3960(6) 0.10916(12) 0.0565(12) Uani 1 1 d . . . C6 C 0.4968(6) 0.4667(6) 0.12534(11) 0.0524(11) Uani 1 1 d . . . C7 C 0.4603(6) 0.4781(6) 0.16968(12) 0.0496(11) Uani 1 1 d . . . C8 C 0.3573(6) 0.3939(5) 0.31285(11) 0.0433(10) Uani 1 1 d . . . C9 C 0.1535(6) 0.3318(5) 0.32405(11) 0.0494(11) Uani 1 1 d . . . H9 H 0.0582 0.2953 0.3022 0.059 Uiso 1 1 calc R . . C10 C 0.0890(6) 0.3232(5) 0.36755(12) 0.0551(12) Uani 1 1 d . . . H10 H -0.0478 0.2788 0.3747 0.066 Uiso 1 1 calc R . . C11 C 0.2283(7) 0.3806(6) 0.40051(12) 0.0582(12) Uani 1 1 d . . . C12 C 0.4309(7) 0.4429(6) 0.38918(11) 0.0594(12) Uani 1 1 d . . . H12 H 0.5263 0.4791 0.4111 0.071 Uiso 1 1 calc R . . C13 C 0.4962(6) 0.4529(5) 0.34553(11) 0.0513(10) Uani 1 1 d . . . H13 H 0.6321 0.4988 0.3384 0.062 Uiso 1 1 calc R . . C14 C 0.1602(8) 0.3726(7) 0.44582(12) 0.0735(14) Uani 1 1 d . . . C15 C 0.1035(8) 0.3676(7) 0.48175(13) 0.110(2) Uani 1 1 d . . . H15 H 0.0577 0.3636 0.5108 0.132 Uiso 1 1 calc R . . F1 F 0.9497(3) 0.2840(4) 0.21113(6) 0.0706(7) Uani 1 1 d . . . F2 F 1.0234(3) 0.2599(3) 0.12560(8) 0.0759(8) Uani 1 1 d . . . F3 F 0.3445(3) 0.5310(3) 0.09779(6) 0.0742(8) Uani 1 1 d . . . F4 F 0.2736(3) 0.5561(3) 0.18366(6) 0.0630(7) Uani 1 1 d . . . N1 N 0.4086(5) 0.3872(4) 0.26695(8) 0.0457(8) Uani 1 1 d . . . N2 N 0.7024(6) 0.3912(6) 0.06325(11) 0.0860(14) Uani 1 1 d . . . N3 N 0.8819(8) 0.3522(7) 0.04708(13) 0.0926(15) Uani 1 1 d . . . N4 N 1.0275(8) 0.3228(8) 0.02615(13) 0.142(2) Uani 1 1 d . . . O1 O 0.7327(4) 0.5375(4) 0.26698(7) 0.0660(8) 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 0.050(2) 0.034(3) 0.056(2) 0.010(2) -0.017(2) 0.005(2) C2 0.0335(19) 0.040(3) 0.059(2) 0.005(2) -0.0095(19) -0.004(2) C3 0.048(2) 0.037(3) 0.068(3) 0.012(2) -0.017(2) -0.008(2) C4 0.043(2) 0.043(3) 0.072(3) -0.001(3) 0.001(2) -0.007(2) C5 0.068(3) 0.047(3) 0.054(2) 0.005(2) -0.002(2) -0.015(3) C6 0.051(2) 0.053(3) 0.053(2) 0.010(2) -0.014(2) -0.009(3) C7 0.045(2) 0.044(3) 0.060(2) 0.008(2) -0.009(2) -0.008(2) C8 0.041(2) 0.037(3) 0.052(2) 0.003(2) -0.0101(19) 0.006(2) C9 0.045(2) 0.050(3) 0.053(2) -0.003(2) -0.012(2) 0.001(2) C10 0.044(2) 0.059(3) 0.062(2) 0.000(2) -0.007(2) 0.001(2) C11 0.066(3) 0.048(3) 0.060(2) -0.004(2) 0.003(2) 0.013(3) C12 0.068(3) 0.055(3) 0.055(2) -0.014(2) -0.016(2) 0.001(3) C13 0.045(2) 0.049(3) 0.060(2) -0.003(3) -0.012(2) 0.001(3) C14 0.084(3) 0.083(4) 0.054(2) -0.008(3) -0.006(3) 0.001(3) C15 0.128(4) 0.132(5) 0.069(3) -0.016(4) 0.006(3) -0.005(5) F1 0.0545(11) 0.0656(19) 0.0915(14) 0.0130(15) -0.0235(13) 0.0109(15) F2 0.0598(13) 0.0685(19) 0.0994(16) -0.0052(17) 0.0127(14) 0.0081(17) F3 0.0700(14) 0.092(2) 0.0610(12) 0.0205(15) -0.0253(12) -0.0032(17) F4 0.0433(11) 0.080(2) 0.0661(12) 0.0136(14) -0.0075(11) 0.0101(15) N1 0.0429(16) 0.048(2) 0.0464(16) 0.0060(17) -0.0032(16) -0.0017(19) N2 0.093(3) 0.110(4) 0.055(2) -0.008(2) 0.007(2) -0.017(3) N3 0.115(4) 0.091(4) 0.072(3) -0.018(3) 0.006(3) -0.026(4) N4 0.149(5) 0.167(6) 0.110(4) -0.045(4) 0.045(4) -0.038(5) O1 0.0651(15) 0.073(2) 0.0600(15) 0.0125(17) -0.0220(15) -0.0289(19) _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 O1 1.217(4) . ? C1 N1 1.339(4) . ? C1 C2 1.495(5) . ? C2 C3 1.368(5) . ? C2 C7 1.396(5) . ? C3 F1 1.351(4) . ? C3 C4 1.383(5) . ? C4 F2 1.342(4) . ? C4 C5 1.377(5) . ? C5 C6 1.376(5) . ? C5 N2 1.405(4) . ? C6 F3 1.349(4) . ? C6 C7 1.375(4) . ? C7 F4 1.358(4) . ? C8 C9 1.380(5) . ? C8 C13 1.386(4) . ? C8 N1 1.437(4) . ? C9 C10 1.388(5) . ? C9 H9 0.9300 . ? C10 C11 1.390(5) . ? C10 H10 0.9300 . ? C11 C12 1.374(5) . ? C11 C14 1.447(5) . ? C12 C13 1.394(4) . ? C12 H12 0.9300 . ? C13 H13 0.9300 . ? C14 C15 1.152(5) . ? C15 H15 0.9300 . ? N2 N3 1.243(5) . ? N3 N4 1.121(5) . ? 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 C1 N1 127.3(3) . . ? O1 C1 C2 118.0(4) . . ? N1 C1 C2 114.7(3) . . ? C3 C2 C7 114.7(3) . . ? C3 C2 C1 121.2(3) . . ? C7 C2 C1 123.5(4) . . ? F1 C3 C2 118.8(3) . . ? F1 C3 C4 117.5(4) . . ? C2 C3 C4 123.6(4) . . ? F2 C4 C5 120.5(4) . . ? F2 C4 C3 118.9(4) . . ? C5 C4 C3 120.6(4) . . ? C6 C5 C4 117.3(3) . . ? C6 C5 N2 115.1(4) . . ? C4 C5 N2 127.5(4) . . ? F3 C6 C7 118.6(4) . . ? F3 C6 C5 120.3(3) . . ? C7 C6 C5 121.1(4) . . ? F4 C7 C6 118.3(3) . . ? F4 C7 C2 118.9(3) . . ? C6 C7 C2 122.7(4) . . ? C9 C8 C13 119.3(3) . . ? C9 C8 N1 115.4(3) . . ? C13 C8 N1 125.4(3) . . ? C8 C9 C10 120.8(4) . . ? C8 C9 H9 119.6 . . ? C10 C9 H9 119.6 . . ? C9 C10 C11 120.2(4) . . ? C9 C10 H10 119.9 . . ? C11 C10 H10 119.9 . . ? C12 C11 C10 118.8(4) . . ? C12 C11 C14 121.1(4) . . ? C10 C11 C14 120.1(4) . . ? C11 C12 C13 121.3(4) . . ? C11 C12 H12 119.3 . . ? C13 C12 H12 119.3 . . ? C8 C13 C12 119.6(3) . . ? C8 C13 H13 120.2 . . ? C12 C13 H13 120.2 . . ? C15 C14 C11 179.0(6) . . ? C14 C15 H15 180.0 . . ? C1 N1 C8 124.9(3) . . ? N3 N2 C5 117.5(4) . . ? N4 N3 N2 168.6(5) . . ? _diffrn_measured_fraction_theta_max 0.998 _diffrn_reflns_theta_full 27.47 _diffrn_measured_fraction_theta_full 0.998 _refine_diff_density_max 0.199 _refine_diff_density_min -0.201 _refine_diff_density_rms 0.047 _database_code_depnum_ccdc_archive 'CCDC 696107'