# Electronic Supplementary Material (ESI) for CrystEngComm # 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_shelxl _database_code_depnum_ccdc_archive 'CCDC 905485' #TrackingRef '14604_web_deposit_cif_file_0_GrahamSaunders_1349917590.gsbzbzi_2.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C14 H5 F4 N3' _chemical_formula_sum 'C14 H5 F4 N3' _chemical_formula_weight 291.21 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' 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 'C c' 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' _cell_length_a 10.5156(3) _cell_length_b 9.1793(3) _cell_length_c 12.2202(4) _cell_angle_alpha 90.00 _cell_angle_beta 98.3810(10) _cell_angle_gamma 90.00 _cell_volume 1166.97(6) _cell_formula_units_Z 4 _cell_measurement_temperature 89(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min 2 _cell_measurement_theta_max 26 _exptl_crystal_description brick _exptl_crystal_colour colourless _exptl_crystal_size_max 0.40 _exptl_crystal_size_mid 0.32 _exptl_crystal_size_min 0.25 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.658 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 584 _exptl_absorpt_coefficient_mu 0.147 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.9435 _exptl_absorpt_correction_T_max 0.9642 _exptl_absorpt_process_details SADABS _exptl_special_details ; ? ; _diffrn_ambient_temperature 89(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 ? _diffrn_measurement_method ? _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 14129 _diffrn_reflns_av_R_equivalents 0.0272 _diffrn_reflns_av_sigmaI/netI 0.0197 _diffrn_reflns_limit_h_min -13 _diffrn_reflns_limit_h_max 13 _diffrn_reflns_limit_k_min -12 _diffrn_reflns_limit_k_max 12 _diffrn_reflns_limit_l_min -15 _diffrn_reflns_limit_l_max 16 _diffrn_reflns_theta_min 2.96 _diffrn_reflns_theta_max 28.13 _reflns_number_total 2768 _reflns_number_gt 2755 _reflns_threshold_expression >2sigma(I) _computing_data_collection ? _computing_cell_refinement ? _computing_data_reduction ? _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics ? _computing_publication_material ? _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^)+(0.0489P)^2^+0.2500P] 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_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881' _refine_ls_abs_structure_Flack 0.4(3) _refine_ls_number_reflns 2768 _refine_ls_number_parameters 190 _refine_ls_number_restraints 2 _refine_ls_R_factor_all 0.0251 _refine_ls_R_factor_gt 0.0250 _refine_ls_wR_factor_ref 0.0709 _refine_ls_wR_factor_gt 0.0708 _refine_ls_goodness_of_fit_ref 1.076 _refine_ls_restrained_S_all 1.075 _refine_ls_shift/su_max 0.006 _refine_ls_shift/su_mean 0.001 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 0.80950(10) -0.21493(12) 0.59411(9) 0.0193(2) Uani 1 1 d . . . H1 H 0.7752 -0.3105 0.5957 0.023 Uiso 1 1 calc R . . C2 C 0.90615(10) -0.01492(11) 0.64287(9) 0.0176(2) Uani 1 1 d . . . C3 C 0.86415(10) -0.00019(11) 0.52883(9) 0.01562(19) Uani 1 1 d . . . C4 C 0.89154(10) 0.12163(12) 0.46834(9) 0.0187(2) Uani 1 1 d . . . H4 H 0.8627 0.1302 0.3912 0.022 Uiso 1 1 calc R . . C5 C 0.96389(11) 0.23019(12) 0.52806(10) 0.0222(2) Uani 1 1 d . . . H5 H 0.9843 0.3159 0.4907 0.027 Uiso 1 1 calc R . . C6 C 1.00770(10) 0.21660(13) 0.64210(10) 0.0235(2) Uani 1 1 d . . . H6 H 1.0569 0.2931 0.6796 0.028 Uiso 1 1 calc R . . C7 C 0.98066(10) 0.09418(13) 0.70097(9) 0.0215(2) Uani 1 1 d . . . H7 H 1.0115 0.0847 0.7777 0.026 Uiso 1 1 calc R . . C8 C 0.76100(10) -0.18496(11) 0.39097(8) 0.01561(19) Uani 1 1 d . . . C9 C 0.80482(10) -0.31971(12) 0.35898(9) 0.0184(2) Uani 1 1 d . . . C10 C 0.76950(10) -0.37158(12) 0.25276(10) 0.0204(2) Uani 1 1 d . . . C11 C 0.69121(11) -0.29002(14) 0.17430(9) 0.0206(2) Uani 1 1 d . . . C12 C 0.64644(10) -0.15651(13) 0.20618(9) 0.0195(2) Uani 1 1 d . . . C13 C 0.67909(10) -0.10522(12) 0.31302(9) 0.0176(2) Uani 1 1 d . . . C14 C 0.66076(12) -0.34183(15) 0.06234(10) 0.0269(2) Uani 1 1 d . . . F9 F 0.88598(7) -0.39794(7) 0.42989(6) 0.02524(16) Uani 1 1 d . . . F10 F 0.81665(8) -0.49911(8) 0.22494(7) 0.03102(18) Uani 1 1 d . . . F12 F 0.57110(7) -0.07523(9) 0.13253(6) 0.02781(16) Uani 1 1 d . . . F13 F 0.63164(7) 0.02178(7) 0.34192(6) 0.02328(15) Uani 1 1 d . . . N1 N 0.80080(9) -0.13174(9) 0.49842(7) 0.01580(17) Uani 1 1 d . . . N2 N 0.86897(9) -0.14980(11) 0.68142(8) 0.02055(19) Uani 1 1 d . . . N3 N 0.63858(13) -0.38424(17) -0.02624(10) 0.0395(3) 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 0.0217(5) 0.0203(5) 0.0157(5) 0.0030(4) 0.0024(4) 0.0012(4) C2 0.0162(5) 0.0219(5) 0.0149(5) -0.0021(4) 0.0022(4) 0.0025(4) C3 0.0148(4) 0.0171(4) 0.0147(5) -0.0032(3) 0.0014(3) 0.0014(3) C4 0.0196(4) 0.0181(4) 0.0183(5) 0.0002(4) 0.0030(4) 0.0015(4) C5 0.0216(5) 0.0187(4) 0.0266(5) -0.0023(4) 0.0048(4) -0.0006(4) C6 0.0194(5) 0.0239(5) 0.0269(6) -0.0102(4) 0.0022(4) -0.0014(4) C7 0.0182(5) 0.0297(5) 0.0156(5) -0.0076(4) -0.0001(4) 0.0022(4) C8 0.0160(4) 0.0170(4) 0.0134(4) -0.0005(3) 0.0010(3) -0.0018(3) C9 0.0177(5) 0.0188(5) 0.0178(5) -0.0003(4) -0.0003(4) -0.0003(4) C10 0.0211(5) 0.0177(4) 0.0224(6) -0.0070(4) 0.0037(4) -0.0031(4) C11 0.0199(5) 0.0274(5) 0.0143(5) -0.0047(4) 0.0018(4) -0.0079(4) C12 0.0174(5) 0.0245(5) 0.0153(5) 0.0030(4) -0.0019(4) -0.0033(4) C13 0.0174(4) 0.0185(5) 0.0164(5) -0.0009(4) 0.0009(4) -0.0001(4) C14 0.0243(5) 0.0360(6) 0.0207(6) -0.0068(5) 0.0037(4) -0.0121(5) F9 0.0273(3) 0.0207(3) 0.0254(4) -0.0007(2) -0.0038(3) 0.0077(3) F10 0.0352(4) 0.0233(3) 0.0338(4) -0.0137(3) 0.0025(3) 0.0029(3) F12 0.0280(3) 0.0329(4) 0.0193(3) 0.0055(3) -0.0074(3) 0.0005(3) F13 0.0254(3) 0.0204(3) 0.0226(3) -0.0005(2) -0.0016(3) 0.0071(2) N1 0.0189(4) 0.0163(4) 0.0116(4) 0.0002(3) 0.0003(3) -0.0001(3) N2 0.0222(4) 0.0252(4) 0.0140(4) 0.0023(3) 0.0017(3) 0.0017(3) N3 0.0380(6) 0.0582(8) 0.0222(6) -0.0108(5) 0.0041(5) -0.0229(6) _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 N2 1.3009(14) . ? C1 N1 1.3883(13) . ? C2 C7 1.3995(14) . ? C2 N2 1.4005(14) . ? C2 C3 1.4058(15) . ? C3 C4 1.3935(14) . ? C3 N1 1.4028(13) . ? C4 C5 1.3938(15) . ? C5 C6 1.4081(17) . ? C6 C7 1.3859(17) . ? C8 C13 1.3950(13) . ? C8 C9 1.3956(14) . ? C8 N1 1.4063(13) . ? C9 F9 1.3339(12) . ? C9 C10 1.3817(15) . ? C10 F10 1.3345(13) . ? C10 C11 1.3883(16) . ? C11 C12 1.3889(16) . ? C11 C14 1.4397(15) . ? C12 F12 1.3366(12) . ? C12 C13 1.3832(14) . ? C13 F13 1.3357(12) . ? C14 N3 1.1420(18) . ? 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 N2 C1 N1 113.75(10) . . ? C7 C2 N2 128.69(10) . . ? C7 C2 C3 120.39(10) . . ? N2 C2 C3 110.84(9) . . ? C4 C3 N1 132.62(10) . . ? C4 C3 C2 122.93(10) . . ? N1 C3 C2 104.37(9) . . ? C3 C4 C5 115.80(10) . . ? C4 C5 C6 121.99(11) . . ? C7 C6 C5 121.55(10) . . ? C6 C7 C2 117.32(10) . . ? C13 C8 C9 118.03(9) . . ? C13 C8 N1 121.70(9) . . ? C9 C8 N1 120.26(9) . . ? F9 C9 C10 118.93(10) . . ? F9 C9 C8 120.08(9) . . ? C10 C9 C8 120.94(10) . . ? F10 C10 C9 118.86(11) . . ? F10 C10 C11 120.14(10) . . ? C9 C10 C11 120.94(10) . . ? C10 C11 C12 118.25(10) . . ? C10 C11 C14 120.37(11) . . ? C12 C11 C14 121.37(11) . . ? F12 C12 C13 119.13(10) . . ? F12 C12 C11 119.70(10) . . ? C13 C12 C11 121.16(10) . . ? F13 C13 C12 119.72(10) . . ? F13 C13 C8 119.65(9) . . ? C12 C13 C8 120.64(10) . . ? N3 C14 C11 178.80(16) . . ? C1 N1 C3 106.25(9) . . ? C1 N1 C8 124.71(9) . . ? C3 N1 C8 127.70(9) . . ? C1 N2 C2 104.76(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 C7 C2 C3 C4 -1.02(15) . . . . ? N2 C2 C3 C4 -177.89(9) . . . . ? C7 C2 C3 N1 176.31(9) . . . . ? N2 C2 C3 N1 -0.56(11) . . . . ? N1 C3 C4 C5 -176.60(11) . . . . ? C2 C3 C4 C5 -0.12(14) . . . . ? C3 C4 C5 C6 0.70(15) . . . . ? C4 C5 C6 C7 -0.16(17) . . . . ? C5 C6 C7 C2 -0.97(15) . . . . ? N2 C2 C7 C6 177.78(10) . . . . ? C3 C2 C7 C6 1.52(14) . . . . ? C13 C8 C9 F9 178.23(9) . . . . ? N1 C8 C9 F9 -0.80(15) . . . . ? C13 C8 C9 C10 0.89(15) . . . . ? N1 C8 C9 C10 -178.14(10) . . . . ? F9 C9 C10 F10 0.74(15) . . . . ? C8 C9 C10 F10 178.11(9) . . . . ? F9 C9 C10 C11 -176.26(10) . . . . ? C8 C9 C10 C11 1.12(16) . . . . ? F10 C10 C11 C12 -178.65(9) . . . . ? C9 C10 C11 C12 -1.70(17) . . . . ? F10 C10 C11 C14 -0.30(17) . . . . ? C9 C10 C11 C14 176.65(10) . . . . ? C10 C11 C12 F12 179.86(9) . . . . ? C14 C11 C12 F12 1.52(16) . . . . ? C10 C11 C12 C13 0.28(16) . . . . ? C14 C11 C12 C13 -178.05(11) . . . . ? F12 C12 C13 F13 2.24(15) . . . . ? C11 C12 C13 F13 -178.18(9) . . . . ? F12 C12 C13 C8 -177.84(9) . . . . ? C11 C12 C13 C8 1.74(16) . . . . ? C9 C8 C13 F13 177.62(9) . . . . ? N1 C8 C13 F13 -3.36(14) . . . . ? C9 C8 C13 C12 -2.30(14) . . . . ? N1 C8 C13 C12 176.72(10) . . . . ? C10 C11 C14 N3 -28(7) . . . . ? C12 C11 C14 N3 151(7) . . . . ? N2 C1 N1 C3 1.16(12) . . . . ? N2 C1 N1 C8 168.81(10) . . . . ? C4 C3 N1 C1 176.66(11) . . . . ? C2 C3 N1 C1 -0.29(10) . . . . ? C4 C3 N1 C8 9.49(18) . . . . ? C2 C3 N1 C8 -167.46(10) . . . . ? C13 C8 N1 C1 138.38(10) . . . . ? C9 C8 N1 C1 -42.62(15) . . . . ? C13 C8 N1 C3 -56.66(15) . . . . ? C9 C8 N1 C3 122.34(11) . . . . ? N1 C1 N2 C2 -1.46(12) . . . . ? C7 C2 N2 C1 -175.31(10) . . . . ? C3 C2 N2 C1 1.24(11) . . . . ? _diffrn_measured_fraction_theta_max 0.994 _diffrn_reflns_theta_full 27.50 _diffrn_measured_fraction_theta_full 0.996 _refine_diff_density_max 0.322 _refine_diff_density_min -0.169 _refine_diff_density_rms 0.040