# 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_TFP _database_code_depnum_ccdc_archive 'CCDC 909676' #TrackingRef 'deposit_corr_CCDC_909676_909677.cif' _audit_creation_date '24-Oct-10 T17:22:57-00:00' _audit_creation_method 'XD routine XDCIF' #----------------------------------------------------------------------------# # CHEMICAL INFORMATION # #----------------------------------------------------------------------------# _chemical_name_common 2,3,5,6-tetrafluoropyridine _chemical_formula_moiety 'C5 H F4 N' _chemical_formula_sum 'C5 H F4 N' _chemical_formula_weight 151.07 #----------------------------------------------------------------------------# # UNIT CELL INFORMATION # #----------------------------------------------------------------------------# loop_ _space_group_symop_id _space_group_symop_operation_xyz 1 +X,+Y,+Z 2 1/2-X,-Y,1/2+Z 3 1/2+X,1/2-Y,1/2-Z 4 -X,1/2+Y,-Z 5 -X,-Y,-Z 6 1/2+X,+Y,1/2-Z 7 1/2-X,1/2+Y,1/2+Z 8 +X,1/2-Y,+Z _cell_length_a 6.6796(2) _cell_length_b 7.6493(3) _cell_length_c 10.2128(5) _cell_angle_alpha 90.000 _cell_angle_beta 90.000 _cell_angle_gamma 90.000 _cell_volume 521.82(4) _cell_formula_units_Z 4 _cell_measurement_temperature 100(2) _cell_measurement_reflns_used 11558 _cell_measurement_theta_min 3 _cell_measurement_theta_max 50 _symmetry_cell_setting orthorhombic _symmetry_space_group_name_H-M Pnma _computing_molecular_graphics 'Volkov et al, (2006)' _computing_publication_material 'Volkov et al, (2006)' #----------------------------------------------------------------------------# # CRYSTAL INFORMATION # #----------------------------------------------------------------------------# _exptl_crystal_description 'capillary like' _exptl_crystal_colour colorless _exptl_crystal_size_max .35 _exptl_crystal_size_mid .3 _exptl_crystal_size_min .3 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.923 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 296 #----------------------------------------------------------------------------# # ABSORPTION CORRECTION # #----------------------------------------------------------------------------# _exptl_absorpt_coefficient_mu 0.217 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.92717 _exptl_absorpt_correction_T_max 0.93756 _exptl_absorpt_process_details 'SADABS - Bruker Nonius area detector scaling and absorption correction - V2.10' #----------------------------------------------------------------------------# # DATA COLLECTION # #----------------------------------------------------------------------------# _diffrn_ambient_temperature 100(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_measurement_device_type KappaCCD _diffrn_measurement_method CCD _diffrn_detector_area_resol_mean ? _diffrn_reflns_number 35952 _reflns_number_total 2841 _reflns_number_gt 1807 _reflns_threshold_expression >3sigma(I) _diffrn_reflns_av_R_equivalents 0.0289 _diffrn_reflns_av_sigmaI/netI 0.0133 _diffrn_reflns_limit_h_min -14 _diffrn_reflns_limit_h_max 14 _diffrn_reflns_limit_k_min -16 _diffrn_reflns_limit_k_max 16 _diffrn_reflns_limit_l_min -22 _diffrn_reflns_limit_l_max 21 _diffrn_reflns_theta_min 3.64 _diffrn_reflns_theta_max 50.00 _diffrn_measured_fraction_theta_max 0.994 _diffrn_reflns_theta_full 50.00 _diffrn_measured_fraction_theta_full 0.994 #----------------------------------------------------------------------------# # COMPUTER PROGRAMS USED # #----------------------------------------------------------------------------# _computing_structure_refinement 'Volkov et al, (2006)' _refine_ls_extinction_coef 0.027(2) _refine_ls_extinction_expression ; Becker, P.J. & Coppens, P. (1974) Acta Cryst., A30, 129-153. ; _refine_ls_extinction_method 'Becker-Coppens type 1 Lorentzian isotropic' _refine_ls_goodness_of_fit_ref 2.106 _refine_ls_matrix_type full _refine_ls_number_parameters 189 _refine_ls_number_reflns 1807 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.041 _refine_ls_R_factor_gt 0.0202 _refine_ls_R_Fsqd_factor 0.0184 _refine_ls_shift/su_max 0.00001 _refine_ls_structure_factor_coef Fsqd _refine_ls_weighting_details ; Standard weighting scheme was used: calc w2 = 1/[s^2^(Fo^2^)] ; _refine_ls_weighting_scheme calc _refine_ls_wR_factor_ref 0.0221 _refine_diff_density_max 0.130 _refine_diff_density_min -0.189 _refine_diff_density_rms 0.034 #----------------------------------------------------------------------------# # REFINEMENT INFORMATION # #----------------------------------------------------------------------------# _refine_special_details ; Multipole refinement up to hexadecapoles ; #----------------------------------------------------------------------------# # ATOMIC TYPES, COORDINATES AND THERMAL PARAMETERS # #----------------------------------------------------------------------------# _atom_type_scat_source 'Volkov et al, (2006)' loop_ _atom_site_label _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_occupancy _atom_site_symmetry_multiplicity F(1) 0.45518(9) 0.54535(6) 0.71684(5) 0.028 1 8 F(2) 0.21790(7) 0.55906(5) 0.50098(5) 0.026 1 8 N(1) 0.45200(7) 0.25 0.71549(4) 0.02 1 4 C(1) 0.39204(4) 0.39661(5) 0.66142(3) 0.018 1 8 C(2) 0.27177(4) 0.40407(4) 0.55070(3) 0.017 1 8 C(3) 0.20995(6) 0.25 0.49255(4) 0.018 1 4 H(3) 0.1256(13) 0.25 0.4143(9) 0.02115(9) 1 4 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 F(1) 0.0320(2) 0.02446(18) 0.02842(18) -0.00829(14) -0.00083(18) -0.00732(15) F(2) 0.02615(18) 0.01864(14) 0.03248(18) 0.00649(13) -0.00041(17) 0.00159(14) N(1) 0.01921(18) 0.0240(2) 0.01597(15) 0 -0.00222(16) 0 C(1) 0.01828(11) 0.01941(12) 0.01719(10) -0.00230(11) 0.00043(8) -0.00227(10) C(2) 0.01674(11) 0.01648(11) 0.01847(10) 0.00145(10) 0.00060(8) 0.00009(10) C(3) 0.01705(16) 0.01929(16) 0.01654(16) 0 -0.00193(13) 0 loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_1 _geom_bond_site_symmetry_2 _geom_bond_publ_flag F(1) C(1) 1.3389(5) 1_555 1_555 yes F(2) C(2) 1.3389(4) 1_555 1_555 yes N(1) C(1) 1.3126(4) 1_555 1_555 yes N(1) C(1) 1.3126(4) 1_555 8_555 yes C(1) C(2) 1.3883(4) 1_555 1_555 yes C(2) C(3) 1.3828(4) 1_555 8_555 yes C(2) C(3) 1.3828(4) 1_555 1_555 yes C(3) H(3) 0.978(10) 1_555 8_555 yes C(3) H(3) 0.978(10) 1_555 1_555 yes 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_2 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C(1) N(1) C(1) 117.37(5) 1_555 1_555 8_555 yes F(1) C(1) N(1) 116.87(4) 1_555 1_555 8_555 yes F(1) C(1) N(1) 116.87(4) 1_555 1_555 1_555 yes F(1) C(1) C(2) 119.45(4) 1_555 1_555 1_555 yes N(1) C(1) C(2) 123.67(4) 8_555 1_555 1_555 yes N(1) C(1) C(2) 123.67(4) 1_555 1_555 1_555 yes F(2) C(2) C(1) 120.05(4) 1_555 1_555 1_555 yes F(2) C(2) C(3) 120.76(4) 1_555 1_555 8_555 yes F(2) C(2) C(3) 120.76(4) 1_555 1_555 1_555 yes C(1) C(2) C(3) 119.18(3) 1_555 1_555 8_555 yes C(1) C(2) C(3) 119.18(3) 1_555 1_555 1_555 yes C(2) C(3) C(2) 116.92(4) 1_555 1_555 8_555 yes C(2) C(3) H(3) 121.54(2) 8_555 1_555 8_555 yes C(2) C(3) H(3) 121.54(2) 8_555 1_555 1_555 yes C(2) C(3) H(3) 121.54(2) 1_555 1_555 8_555 yes C(2) C(3) H(3) 121.54(2) 1_555 1_555 1_555 yes 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 F(1) C(1) C(2) F(2) -0.74(4) 1_555 1_555 1_555 1_555 yes F(1) C(1) C(2) C(3) 178.87(5) 1_555 1_555 1_555 1_555 yes N(1) C(1) C(2) F(2) -179.61(5) 1_555 1_555 1_555 1_555 yes N(1) C(1) C(2) F(2) -179.61(5) 8_555 1_555 1_555 1_555 yes N(1) C(1) C(2) C(3) 0.00(3) 8_555 1_555 1_555 1_555 yes N(1) C(1) C(2) C(3) 0.00(3) 1_555 1_555 1_555 1_555 yes C(1) N(1) C(1) F(1) -179.56(5) 8_555 1_555 1_555 1_555 yes C(1) N(1) C(1) C(2) -0.67(3) 8_555 1_555 1_555 1_555 yes C(2) C(3) C(2) F(2) -179.73(5) 8_555 1_555 1_555 1_555 yes C(2) C(3) C(2) C(1) 0.66(3) 8_555 1_555 1_555 1_555 yes C(3) C(2) C(1) F(1) 178.87(5) 8_555 1_555 1_555 1_555 yes C(3) C(2) C(1) N(1) 0.00(3) 8_555 1_555 1_555 1_555 yes H(3) C(3) C(2) F(2) -0.2(5) 8_555 1_555 1_555 1_555 yes H(3) C(3) C(2) F(2) -0.2(5) 1_555 1_555 1_555 1_555 yes H(3) C(3) C(2) C(1) -179.8(5) 1_555 1_555 1_555 1_555 yes H(3) C(3) C(2) C(1) -179.8(5) 8_555 1_555 1_555 1_555 yes loop_ _atom_local_axes_atom_label _atom_local_axes_atom0 _atom_local_axes_ax1 _atom_local_axes_atom1 _atom_local_axes_atom2 _atom_local_axes_ax2 F(1) C(1) Z F(1) N(1) Y F(2) C(2) Z F(2) C(1) Y N(1) DUM0 Z N(1) C(3) Y C(1) N(1) Z C(1) F(1) Y C(2) F(2) Z C(2) C(3) Y C(3) DUM1 Z C(3) N(1) Y H(3) C(3) Z H(3) F(2) Y loop_ _atom_rho_multipole_atom_label _atom_rho_multipole_coeff_Pv _atom_rho_multipole_coeff_P00 _atom_rho_multipole_coeff_P11 _atom_rho_multipole_coeff_P1-1 _atom_rho_multipole_coeff_P10 _atom_rho_multipole_coeff_P20 _atom_rho_multipole_coeff_P21 _atom_rho_multipole_coeff_P2-1 _atom_rho_multipole_coeff_P22 _atom_rho_multipole_coeff_P2-2 _atom_rho_multipole_coeff_P30 _atom_rho_multipole_coeff_P31 _atom_rho_multipole_coeff_P3-1 _atom_rho_multipole_coeff_P32 _atom_rho_multipole_coeff_P3-2 _atom_rho_multipole_coeff_P33 _atom_rho_multipole_coeff_P3-3 _atom_rho_multipole_coeff_P40 _atom_rho_multipole_coeff_P41 _atom_rho_multipole_coeff_P4-1 _atom_rho_multipole_coeff_P42 _atom_rho_multipole_coeff_P4-2 _atom_rho_multipole_coeff_P43 _atom_rho_multipole_coeff_P4-3 _atom_rho_multipole_coeff_P44 _atom_rho_multipole_coeff_P4-4 _atom_rho_multipole_kappa _atom_rho_multipole_kappa_prime0 _atom_rho_multipole_kappa_prime1 _atom_rho_multipole_kappa_prime2 _atom_rho_multipole_kappa_prime3 _atom_rho_multipole_kappa_prime4 _atom_rho_multipole_radial_slater_n0 _atom_rho_multipole_radial_slater_zeta0 _atom_rho_multipole_radial_slater_n1 _atom_rho_multipole_radial_slater_zeta1 _atom_rho_multipole_radial_slater_n2 _atom_rho_multipole_radial_slater_zeta2 _atom_rho_multipole_radial_slater_n3 _atom_rho_multipole_radial_slater_zeta3 _atom_rho_multipole_radial_slater_n4 _atom_rho_multipole_radial_slater_zeta4 F(1) 7.076(18) 0 -0.044(10) -0.015(12) 0.040(10) -0.077(12) -0.010(10) 0.003(11) 0.010(12) 0.017(11) 0.009(6) 0.035(5) 0.068(6) 0.015(6) -0.024(6) 0.029(5) 0.016(5) 0.009(7) 0.020(6) 0.026(7) -0.019(7) 0.003(7) 0.005(7) 0.019(7) 0.005(7) -0.003(7) 0.9939(19) 0.91(4) 0.906412 0.906412 0.906412 0.906412 2 5.1078857142857 2 5.1078857142857 2 5.1078857142857 3 5.1078857142857 4 5.1078857142857 F(2) 7.071(19) 0 -0.004(9) 0.057(10) -0.010(9) -0.106(11) 0.005(10) 0.008(10) -0.001(11) 0.039(10) 0.017(6) 0.008(5) -0.033(5) 0.021(5) -0.005(5) 0.000(5) 0.007(5) 0.002(7) 0.010(6) -0.012(6) -0.013(6) -0.003(7) -0.001(6) -0.009(6) 0.009(6) -0.004(6) 0.9939(19) 0.91(4) 0.906412 0.906412 0.906412 0.906412 2 5.1078857142857 2 5.1078857142857 2 5.1078857142857 3 5.1078857142857 4 5.1078857142857 N(1) 2.59(4) 0 0.002(8) -0.010(11) 0 0.030(12) 0 0 -0.091(7) -0.019(6) 0 -0.017(7) 0.111(12) 0 0 0.003(5) -0.015(5) -0.008(9) 0 0 -0.037(9) -0.004(7) 0 0 0.014(5) 0.006(5) 0.985(5) 0.81(2) 0.812395 0.812395 0.812395 0.812395 2 3.83936 2 3.83936 2 3.83936 3 3.83936 4 3.83936 C(1) 3.86(4) 0 -0.001(10) -0.155(15) 0.00(2) 0.129(17) 0.017(10) 0.075(13) -0.100(10) 0.002(8) 0.281(16) 0.000(10) -0.026(13) 0.250(12) 0.016(9) 0.022(8) -0.066(9) -0.054(17) 0.001(11) 0.045(16) -0.022(15) -0.004(13) -0.010(11) 0.021(13) 0.024(9) -0.015(9) 0.998(4) 0.912(10) 0.911622 0.911622 0.911622 0.911622 2 3.1762 2 3.1762 2 3.1762 3 3.1762 4 3.1762 C(2) 3.90(3) 0 0.004(9) 0.001(15) -0.111(15) 0.004(12) -0.026(8) -0.024(12) -0.166(11) -0.029(9) 0.343(14) 0.018(8) 0.016(12) 0.151(11) -0.003(9) -0.008(9) 0.019(9) 0.084(15) -0.013(11) -0.008(18) -0.003(13) -0.013(12) 0.003(10) -0.034(11) 0.032(10) 0.003(9) 0.998(4) 0.912(10) 0.911622 0.911622 0.911622 0.911622 2 3.1762 2 3.1762 2 3.1762 3 3.1762 4 3.1762 C(3) 2.07(2) 0 -0.004(7) 0.004(12) 0 0.041(9) 0 0 -0.093(8) -0.001(6) 0 0.003(7) 0.146(10) 0 0 -0.009(6) 0.046(6) 0.001(9) 0 0 -0.016(9) 0.002(8) 0 0 0.010(6) -0.007(6) 0.998(4) 0.912(10) 0.911622 0.911622 0.911622 0.911622 2 3.1762 2 3.1762 2 3.1762 3 3.1762 4 3.1762 H(3) 0.432(14) 0 0 0 0 -0.008(6) 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 1.1 1.18 1.18 1.18 1.18 1.18 0 2 1 2 2 2 3 2 4 2 _audit_conform_dict_location ftp://ftp.iucr.org/pub/cif_core.dic _audit_conform_dict_name cif_core.dic _audit_conform_dict_version 2.3 data_PFP _database_code_depnum_ccdc_archive 'CCDC 909677' #TrackingRef 'deposit_corr_CCDC_909676_909677.cif' _audit_creation_date '19-Oct-10 T10:19:01-00:00' _audit_creation_method 'XD routine XDCIF' _audit_conform_dict_name cif_core.dic _audit_conform_dict_version 2.3 _audit_conform_dict_location ftp://ftp.iucr.org/pub/cif_core.dic #----------------------------------------------------------------------------# # CHEMICAL INFORMATION # #----------------------------------------------------------------------------# _chemical_name_common 'Pyridine, 2,3,4,5,6-pentafluoro-' _chemical_melting_point 231 _chemical_formula_moiety 'C5 F5 N' _chemical_formula_sum 'C5 F5 N' _chemical_formula_weight 169.06 #----------------------------------------------------------------------------# # UNIT CELL INFORMATION # #----------------------------------------------------------------------------# loop_ _space_group_symop_id _space_group_symop_operation_xyz 1 +X,+Y,+Z 2 1/2-X,1/2+Y,1/2-Z 3 -X,-Y,-Z 4 1/2+X,1/2-Y,1/2+Z _cell_length_a 10.8764(7) _cell_length_b 10.2849(10) _cell_length_c 11.1336(15) _cell_angle_alpha 90 _cell_angle_beta 116.979(5) _cell_angle_gamma 90 _cell_volume 1109.9(2) _cell_formula_units_Z 8 _cell_measurement_temperature 100(2) _symmetry_cell_setting Monoclinic _symmetry_space_group_name_H-M 'P 21/n' _symmetry_space_group_name_Hall '-P 2yn' #----------------------------------------------------------------------------# # CRYSTAL INFORMATION # #----------------------------------------------------------------------------# _exptl_crystal_description 'capillary like' _exptl_crystal_colour colorless _exptl_crystal_size_max 0.35 _exptl_crystal_size_mid 0.30 _exptl_crystal_size_min 0.30 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 2.023 _exptl_crystal_density_method 'not measured' #----------------------------------------------------------------------------# # ABSORPTION CORRECTION # #----------------------------------------------------------------------------# _exptl_crystal_F_000 656 _exptl_absorpt_coefficient_mu 0.241 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.8889 _exptl_absorpt_correction_T_max 0.9312 _exptl_absorpt_process_details 'SADABS - Bruker Nonius area detector scaling and absorption correction - V2.10' #----------------------------------------------------------------------------# # DATA COLLECTION # #----------------------------------------------------------------------------# _diffrn_ambient_temperature 100(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 KappaCCD _diffrn_measurement_method CCD _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 120270 _diffrn_reflns_av_R_equivalents 0.0344 _diffrn_reflns_av_sigmaI/netI 0.0209 _diffrn_reflns_limit_h_min -23 _diffrn_reflns_limit_h_max 23 _diffrn_reflns_limit_k_min -22 _diffrn_reflns_limit_k_max 22 _diffrn_reflns_limit_l_min -23 _diffrn_reflns_limit_l_max 23 _diffrn_reflns_theta_min 2.17 _diffrn_reflns_theta_max 50.0 _reflns_number_total 11508 _reflns_number_gt 6265 _reflns_threshold_expression >3sigma(I) _diffrn_measured_fraction_theta_max 0.988 _diffrn_reflns_theta_full 50.0 _diffrn_measured_fraction_theta_full 0.988 #----------------------------------------------------------------------------# # COMPUTER PROGRAMS USED # #----------------------------------------------------------------------------# _computing_structure_refinement 'Volkov et al, (2006)' _computing_molecular_graphics 'Volkov et al, (2006)' _computing_publication_material 'Volkov et al, (2006)' #----------------------------------------------------------------------------# # REFINEMENT INFORMATION # #----------------------------------------------------------------------------# _refine_special_details ; Multipole refinement up to octupole ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details ; Standard weighting scheme was used: calc w2 = 1/[s^2^(Fo^2^)] ; _refine_ls_extinction_method none _refine_ls_number_reflns 5782 _refine_ls_number_parameters 553 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.066 _refine_ls_R_factor_gt 0.0295 _refine_ls_wR_factor_ref 0.0326 _refine_ls_R_Fsqd_factor 0.0240 _refine_ls_goodness_of_fit_ref 2.944 _refine_ls_shift/su_max 0 _refine_diff_density_max 0.234 _refine_diff_density_min -0.188 _refine_diff_density_rms 0.046 #----------------------------------------------------------------------------# # ATOMIC TYPES, COORDINATES AND THERMAL PARAMETERS # #----------------------------------------------------------------------------# _atom_type_scat_source 'Volkov et al, (2006)' loop_ _atom_site_label _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_occupancy _atom_site_symmetry_multiplicity F(1) 0.40400(8) 0.23254(10) 0.69327(9) 0.028 1 4 F(2) 0.58422(10) 0.43666(8) 0.78851(10) 0.029 1 4 F(3) 0.85937(9) 0.38226(9) 0.93390(10) 0.029 1 4 F(4) 0.94447(8) 0.12930(9) 0.97959(9) 0.026 1 4 F(5) 0.74898(10) -0.06177(8) 0.86832(10) 0.029 1 4 F(6) 0.80114(11) -0.04608(11) 0.16833(14) 0.037 1 4 F(7) 0.83080(11) -0.01543(12) 0.42458(13) 0.038 1 4 F(8) 0.65961(14) 0.15882(15) 0.46325(13) 0.041 1 4 F(9) 0.46204(11) 0.28670(10) 0.24328(13) 0.033 1 4 F(10) 0.45025(11) 0.24019(12) -0.00308(12) 0.035 1 4 N(1) 0.57908(6) 0.08762(6) 0.77892(6) 0.021 1 4 N(2) 0.62744(7) 0.09897(7) 0.08679(7) 0.024 1 4 C(1) 0.53950(6) 0.20949(7) 0.76169(6) 0.02 1 4 C(2) 0.62887(6) 0.31468(6) 0.81065(6) 0.02 1 4 C(3) 0.76864(6) 0.28691(6) 0.88436(6) 0.019 1 4 C(4) 0.81205(6) 0.15812(6) 0.90621(6) 0.018 1 4 C(5) 0.71142(7) 0.06289(6) 0.84961(6) 0.02 1 4 C(6) 0.71957(6) 0.03643(6) 0.19146(8) 0.023 1 4 C(7) 0.73654(7) 0.05197(7) 0.32204(8) 0.024 1 4 C(8) 0.64956(7) 0.13930(7) 0.34158(8) 0.024 1 4 C(9) 0.55001(7) 0.20471(6) 0.23074(8) 0.022 1 4 C(10) 0.54499(6) 0.17988(6) 0.10605(7) 0.022 1 4 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 F(1) 0.0170(3) 0.0356(4) 0.0246(4) 0.0003(3) 0.0034(3) 0.0027(3) F(2) 0.0336(4) 0.0184(3) 0.0283(4) 0.0011(3) 0.0069(3) 0.0079(3) F(3) 0.0266(3) 0.0207(3) 0.0314(4) -0.0006(3) 0.0069(3) -0.0075(3) F(4) 0.0177(3) 0.0284(3) 0.0275(3) 0.0040(3) 0.0070(3) 0.0041(3) F(5) 0.0337(4) 0.0158(3) 0.0342(4) -0.0004(3) 0.0133(3) 0.0030(3) F(6) 0.0265(4) 0.0335(5) 0.0508(6) -0.0050(5) 0.0183(4) 0.0070(3) F(7) 0.0286(4) 0.0386(5) 0.0355(5) 0.0138(4) 0.0034(4) 0.0028(4) F(8) 0.0463(6) 0.0542(6) 0.0239(5) -0.0027(5) 0.0182(4) -0.0055(5) F(9) 0.0332(4) 0.0266(4) 0.0466(5) -0.0030(4) 0.0259(4) 0.0036(3) F(10) 0.0277(4) 0.0437(5) 0.0302(4) 0.0133(4) 0.0102(4) 0.0115(4) N(1) 0.0195(2) 0.0187(2) 0.0211(2) -0.00163(19) 0.0068(2) -0.00222(18) N(2) 0.0202(2) 0.0281(3) 0.0237(3) -0.0010(2) 0.0104(2) 0.0020(2) C(1) 0.0173(2) 0.0211(3) 0.0183(2) -0.0007(2) 0.00568(18) 0.0004(2) C(2) 0.0204(2) 0.0169(2) 0.0188(2) 0.00040(18) 0.00597(19) 0.00210(19) C(3) 0.0185(2) 0.0163(2) 0.0193(2) 0.00043(19) 0.00571(19) -0.00142(19) C(4) 0.0174(2) 0.0171(2) 0.0196(2) 0.00106(19) 0.00772(18) 0.00088(18) C(5) 0.0213(2) 0.0152(2) 0.0213(2) -0.00082(19) 0.0090(2) 0.00024(19) C(6) 0.0176(2) 0.0221(2) 0.0291(3) -0.0013(2) 0.0096(2) 0.00068(19) C(7) 0.0197(2) 0.0226(3) 0.0256(3) 0.0039(2) 0.0064(2) -0.0016(2) C(8) 0.0251(3) 0.0248(3) 0.0231(3) -0.0004(2) 0.0112(2) -0.0041(2) C(9) 0.0219(2) 0.0184(2) 0.0281(3) -0.0007(2) 0.0140(2) -0.00126(19) C(10) 0.0190(2) 0.0235(2) 0.0237(3) 0.0027(2) 0.0095(2) 0.0016(2) #----------------------------------------------------------------------------# # MULTIPOLE PARAMETERS # #----------------------------------------------------------------------------# loop_ _atom_rho_multipole_atom_label _atom_rho_multipole_coeff_Pv _atom_rho_multipole_coeff_P00 _atom_rho_multipole_coeff_P11 _atom_rho_multipole_coeff_P1-1 _atom_rho_multipole_coeff_P10 _atom_rho_multipole_coeff_P20 _atom_rho_multipole_coeff_P21 _atom_rho_multipole_coeff_P2-1 _atom_rho_multipole_coeff_P22 _atom_rho_multipole_coeff_P2-2 _atom_rho_multipole_coeff_P30 _atom_rho_multipole_coeff_P31 _atom_rho_multipole_coeff_P3-1 _atom_rho_multipole_coeff_P32 _atom_rho_multipole_coeff_P3-2 _atom_rho_multipole_coeff_P33 _atom_rho_multipole_coeff_P3-3 _atom_rho_multipole_coeff_P40 _atom_rho_multipole_coeff_P41 _atom_rho_multipole_coeff_P4-1 _atom_rho_multipole_coeff_P42 _atom_rho_multipole_coeff_P4-2 _atom_rho_multipole_coeff_P43 _atom_rho_multipole_coeff_P4-3 _atom_rho_multipole_coeff_P44 _atom_rho_multipole_coeff_P4-4 _atom_rho_multipole_kappa _atom_rho_multipole_kappa_prime0 _atom_rho_multipole_kappa_prime1 _atom_rho_multipole_kappa_prime2 _atom_rho_multipole_kappa_prime3 _atom_rho_multipole_kappa_prime4 _atom_rho_multipole_radial_slater_n0 _atom_rho_multipole_radial_slater_zeta0 _atom_rho_multipole_radial_slater_n1 _atom_rho_multipole_radial_slater_zeta1 _atom_rho_multipole_radial_slater_n2 _atom_rho_multipole_radial_slater_zeta2 _atom_rho_multipole_radial_slater_n3 _atom_rho_multipole_radial_slater_zeta3 _atom_rho_multipole_radial_slater_n4 _atom_rho_multipole_radial_slater_zeta4 F(1) 7.042(14) 0 0.017(16) 0.004(16) 0.092(15) -0.06(2) 0.032(18) -0.029(18) 0.04(2) 0.01(2) 0.010(9) -0.015(8) 0.029(8) 0.003(8) -0.027(8) 0.002(8) 0.030(8) 0 0 0 0 0 0 0 0 0 0.9944(15) 1.001325 1.001325 1.001325 1.001325 1.001325 2 5.1078857142857 2 5.1078857142857 2 5.1078857142857 3 5.1078857142857 4 5.1078857142857 F(2) 7.064(15) 0 -0.057(17) -0.027(16) 0.021(15) -0.06(2) 0.016(19) 0.009(18) 0.01(2) -0.07(2) 0.051(9) 0.009(9) -0.007(8) 0.019(8) -0.003(8) 0.033(9) -0.080(9) 0 0 0 0 0 0 0 0 0 0.9944(15) 1.001325 1.001325 1.001325 1.001325 1.001325 2 5.1078857142857 2 5.1078857142857 2 5.1078857142857 3 5.1078857142857 4 5.1078857142857 F(3) 7.063(15) 0 0.014(17) 0.023(16) -0.016(15) -0.09(2) 0.008(19) -0.011(18) 0.01(2) 0.04(2) 0.024(9) 0.000(9) -0.020(8) -0.017(8) 0.010(8) -0.037(8) -0.009(8) 0 0 0 0 0 0 0 0 0 0.9944(15) 1.001325 1.001325 1.001325 1.001325 1.001325 2 5.1078857142857 2 5.1078857142857 2 5.1078857142857 3 5.1078857142857 4 5.1078857142857 F(4) 7.068(14) 0 -0.016(15) -0.014(15) 0.055(15) -0.074(19) -0.018(17) 0.002(17) -0.004(19) -0.002(19) 0.011(9) -0.015(8) 0.006(8) -0.002(8) 0.020(8) 0.008(8) -0.032(8) 0 0 0 0 0 0 0 0 0 0.9944(15) 1.001325 1.001325 1.001325 1.001325 1.001325 2 5.1078857142857 2 5.1078857142857 2 5.1078857142857 3 5.1078857142857 4 5.1078857142857 F(5) 7.069(15) 0 -0.014(17) -0.033(16) 0.067(15) -0.06(2) -0.031(19) -0.008(18) 0.02(2) 0.01(2) 0.000(9) 0.018(9) -0.008(8) 0.022(8) -0.016(8) -0.036(8) -0.021(9) 0 0 0 0 0 0 0 0 0 0.9944(15) 1.001325 1.001325 1.001325 1.001325 1.001325 2 5.1078857142857 2 5.1078857142857 2 5.1078857142857 3 5.1078857142857 4 5.1078857142857 F(6) 6.982(16) 0 -0.020(19) -0.13(2) 0.077(18) -0.10(2) -0.03(2) -0.02(2) 0.01(3) -0.03(3) -0.078(11) 0.021(9) 0.051(10) -0.023(9) 0.000(9) 0.022(10) 0.017(10) 0 0 0 0 0 0 0 0 0 0.9944(15) 1.001325 1.001325 1.001325 1.001325 1.001325 2 5.1078857142857 2 5.1078857142857 2 5.1078857142857 3 5.1078857142857 4 5.1078857142857 F(7) 7.075(16) 0 0.035(19) 0.03(2) 0.040(19) -0.08(3) 0.01(2) 0.00(3) 0.03(3) -0.03(3) 0.026(11) -0.017(9) 0.017(11) 0.020(9) -0.018(10) -0.044(10) 0.040(10) 0 0 0 0 0 0 0 0 0 0.9944(15) 1.001325 1.001325 1.001325 1.001325 1.001325 2 5.1078857142857 2 5.1078857142857 2 5.1078857142857 3 5.1078857142857 4 5.1078857142857 F(8) 7.088(18) 0 0.14(2) -0.09(2) 0.11(2) 0.03(3) -0.02(3) 0.05(3) 0.02(3) 0.06(3) 0.001(12) -0.022(10) 0.023(11) 0.061(10) -0.007(11) 0.076(11) 0.127(11) 0 0 0 0 0 0 0 0 0 0.9944(15) 1.001325 1.001325 1.001325 1.001325 1.001325 2 5.1078857142857 2 5.1078857142857 2 5.1078857142857 3 5.1078857142857 4 5.1078857142857 F(9) 7.084(15) 0 -0.053(17) 0.18(2) 0.071(17) -0.04(2) 0.024(19) 0.00(2) -0.06(2) 0.00(2) -0.013(10) -0.027(9) -0.021(10) -0.065(9) -0.018(9) -0.096(9) -0.080(9) 0 0 0 0 0 0 0 0 0 0.9944(15) 1.001325 1.001325 1.001325 1.001325 1.001325 2 5.1078857142857 2 5.1078857142857 2 5.1078857142857 3 5.1078857142857 4 5.1078857142857 F(10) 7.060(15) 0 -0.12(2) -0.15(2) 0.141(18) -0.01(3) -0.01(2) -0.02(2) -0.06(3) -0.05(3) -0.010(11) -0.004(10) 0.027(10) -0.016(9) 0.027(9) 0.024(10) 0.014(10) 0 0 0 0 0 0 0 0 0 0.9944(15) 1.001325 1.001325 1.001325 1.001325 1.001325 2 5.1078857142857 2 5.1078857142857 2 5.1078857142857 3 5.1078857142857 4 5.1078857142857 N(1) 5.25(4) 0 -0.010(11) 0.000(13) -0.001(15) 0.069(16) -0.010(12) -0.014(14) -0.103(12) -0.017(11) 0.122(11) -0.011(9) 0.025(11) 0.074(10) -0.012(9) 0.007(8) -0.042(9) 0 0 0 0 0 0 0 0 0 0.973(3) 0.952142 0.952142 0.952142 0.952142 0.952142 2 3.83936 2 3.83936 2 3.83936 3 3.83936 4 3.83936 N(2) 5.29(4) 0 0.006(11) -0.021(14) -0.001(16) 0.066(17) -0.003(13) -0.028(16) -0.144(13) 0.007(12) 0.150(12) 0.002(10) 0.003(12) 0.051(10) -0.021(10) -0.008(9) -0.025(9) 0 0 0 0 0 0 0 0 0 0.973(3) 0.952142 0.952142 0.952142 0.952142 0.952142 2 3.83936 2 3.83936 2 3.83936 3 3.83936 4 3.83936 C(1) 3.82(3) 0 -0.007(9) -0.150(11) -0.013(14) 0.100(15) -0.001(11) 0.082(13) -0.072(12) 0.012(10) 0.205(12) 0.002(10) -0.041(12) 0.164(10) 0.001(9) -0.012(8) -0.049(9) 0 0 0 0 0 0 0 0 0 1.010(2) 1.14222 1.14222 1.14222 1.14222 1.14222 2 3.1762 2 3.1762 2 3.1762 3 3.1762 4 3.1762 C(2) 3.86(2) 0 -0.007(9) 0.010(12) -0.113(11) -0.035(13) -0.005(10) -0.002(12) -0.108(12) -0.009(11) 0.206(11) 0.005(9) 0.011(11) 0.073(10) -0.022(9) 0.017(9) 0.007(9) 0 0 0 0 0 0 0 0 0 1.010(2) 1.14222 1.14222 1.14222 1.14222 1.14222 2 3.1762 2 3.1762 2 3.1762 3 3.1762 4 3.1762 C(3) 3.84(2) 0 0.001(9) 0.045(11) -0.103(11) 0.013(13) -0.018(10) -0.013(12) -0.137(12) 0.011(10) 0.257(11) -0.004(9) -0.006(11) 0.115(10) 0.007(9) -0.003(9) -0.022(9) 0 0 0 0 0 0 0 0 0 1.010(2) 1.14222 1.14222 1.14222 1.14222 1.14222 2 3.1762 2 3.1762 2 3.1762 3 3.1762 4 3.1762 C(4) 3.97(2) 0 -0.008(9) -0.002(11) -0.123(11) -0.053(13) -0.005(10) 0.020(12) -0.132(11) -0.010(10) 0.247(11) -0.010(9) -0.009(11) 0.109(9) 0.006(9) -0.004(8) 0.007(9) 0 0 0 0 0 0 0 0 0 1.010(2) 1.14222 1.14222 1.14222 1.14222 1.14222 2 3.1762 2 3.1762 2 3.1762 3 3.1762 4 3.1762 C(5) 3.81(3) 0 0.014(9) -0.142(11) -0.002(14) 0.075(15) -0.013(11) 0.032(13) -0.083(11) 0.015(10) 0.191(12) 0.006(10) -0.030(12) 0.160(10) 0.004(9) 0.001(8) -0.053(9) 0 0 0 0 0 0 0 0 0 1.010(2) 1.14222 1.14222 1.14222 1.14222 1.14222 2 3.1762 2 3.1762 2 3.1762 3 3.1762 4 3.1762 C(6) 3.90(3) 0 0.013(10) -0.134(13) -0.023(16) 0.091(17) -0.013(11) 0.041(15) -0.127(12) 0.015(11) 0.229(13) 0.003(10) -0.052(15) 0.210(11) -0.008(10) 0.009(9) -0.056(9) 0 0 0 0 0 0 0 0 0 1.010(2) 1.14222 1.14222 1.14222 1.14222 1.14222 2 3.1762 2 3.1762 2 3.1762 3 3.1762 4 3.1762 C(7) 3.99(3) 0 0.001(9) 0.024(15) -0.089(13) -0.011(16) 0.013(10) 0.024(16) -0.112(13) -0.010(12) 0.224(12) -0.009(9) -0.012(14) 0.070(11) -0.007(10) 0.035(10) 0.014(10) 0 0 0 0 0 0 0 0 0 1.010(2) 1.14222 1.14222 1.14222 1.14222 1.14222 2 3.1762 2 3.1762 2 3.1762 3 3.1762 4 3.1762 C(8) 3.88(3) 0 -0.038(9) -0.030(14) -0.129(14) -0.033(16) -0.011(11) -0.003(15) -0.159(13) 0.011(11) 0.236(13) 0.009(10) -0.016(14) 0.099(11) -0.021(10) -0.006(10) 0.016(10) 0 0 0 0 0 0 0 0 0 1.010(2) 1.14222 1.14222 1.14222 1.14222 1.14222 2 3.1762 2 3.1762 2 3.1762 3 3.1762 4 3.1762 C(9) 3.95(3) 0 0.023(9) -0.014(14) -0.130(12) -0.013(14) 0.005(10) 0.000(15) -0.113(12) 0.014(11) 0.225(12) -0.020(9) -0.017(13) 0.101(10) -0.012(10) -0.002(9) 0.028(10) 0 0 0 0 0 0 0 0 0 1.010(2) 1.14222 1.14222 1.14222 1.14222 1.14222 2 3.1762 2 3.1762 2 3.1762 3 3.1762 4 3.1762 C(10) 3.84(3) 0 0.003(9) -0.172(13) -0.016(15) 0.086(16) -0.011(11) 0.064(15) -0.097(12) -0.001(11) 0.177(12) 0.007(10) -0.025(13) 0.158(11) 0.020(10) 0.001(9) -0.038(9) 0 0 0 0 0 0 0 0 0 1.010(2) 1.14222 1.14222 1.14222 1.14222 1.14222 2 3.1762 2 3.1762 2 3.1762 3 3.1762 4 3.1762 loop_ _atom_local_axes_atom_label _atom_local_axes_atom0 _atom_local_axes_ax1 _atom_local_axes_atom1 _atom_local_axes_atom2 _atom_local_axes_ax2 F(1) C(1) Z F(1) N(1) Y F(2) C(2) Z F(2) C(3) Y F(3) C(3) Z F(3) C(2) Y F(4) C(4) Z F(4) C(3) Y F(5) C(5) Z F(5) N(1) Y F(6) C(6) Z F(6) N(2) Y F(7) C(7) Z F(7) C(6) Y F(8) C(8) Z F(8) C(9) Y F(9) C(9) Z F(9) C(8) Y F(10) C(10) Z F(10) N(2) Y N(1) C(1) Z N(1) C(5) Y N(2) C(6) Z N(2) C(10) Y C(1) N(1) Z C(1) F(1) Y C(2) F(2) Z C(2) C(1) Y C(3) F(3) Z C(3) C(2) Y C(4) F(4) Z C(4) C(5) Y C(5) N(1) Z C(5) F(5) Y C(6) N(2) Z C(6) F(6) Y C(7) F(7) Z C(7) C(6) Y C(8) F(8) Z C(8) C(9) Y C(9) F(9) Z C(9) C(10) Y C(10) N(2) Z C(10) F(10) Y #----------------------------------------------------------------------------# # MOLECULAR GEOMETRY # #----------------------------------------------------------------------------# loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_1 _geom_bond_site_symmetry_2 _geom_bond_publ_flag F(1) C(1) 1.3379(9) 1_555 1_555 yes F(2) C(2) 1.3274(9) 1_555 1_555 yes F(3) C(3) 1.3213(9) 1_555 1_555 yes F(4) C(4) 1.3275(9) 1_555 1_555 yes F(5) C(5) 1.3330(9) 1_555 1_555 yes F(6) C(6) 1.3345(11) 1_555 1_555 yes F(7) C(7) 1.3315(11) 1_555 1_555 yes F(8) C(8) 1.3239(13) 1_555 1_555 yes F(9) C(9) 1.3293(10) 1_555 1_555 yes F(10) C(10) 1.3367(11) 1_555 1_555 yes N(1) C(1) 1.3108(8) 1_555 1_555 yes N(1) C(5) 1.3146(8) 1_555 1_555 yes N(2) C(6) 1.3101(9) 1_555 1_555 yes N(2) C(10) 1.3104(8) 1_555 1_555 yes C(1) C(2) 1.3898(8) 1_555 1_555 yes C(2) C(3) 1.3907(8) 1_555 1_555 yes C(3) C(4) 1.3901(8) 1_555 1_555 yes C(4) C(5) 1.3887(8) 1_555 1_555 yes C(6) C(7) 1.3892(10) 1_555 1_555 yes C(7) C(8) 1.3914(10) 1_555 1_555 yes C(8) C(9) 1.3912(9) 1_555 1_555 yes C(9) C(10) 1.3880(9) 1_555 1_555 yes 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_2 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C(1) N(1) C(5) 118.06(6) 1_555 1_555 1_555 yes C(6) N(2) C(10) 118.06(7) 1_555 1_555 1_555 yes F(1) C(1) N(1) 117.16(7) 1_555 1_555 1_555 yes F(1) C(1) C(2) 118.63(7) 1_555 1_555 1_555 yes N(1) C(1) C(2) 124.20(6) 1_555 1_555 1_555 yes F(2) C(2) C(1) 122.07(7) 1_555 1_555 1_555 yes F(2) C(2) C(3) 120.90(7) 1_555 1_555 1_555 yes C(1) C(2) C(3) 117.03(6) 1_555 1_555 1_555 yes F(3) C(3) C(2) 120.23(7) 1_555 1_555 1_555 yes F(3) C(3) C(4) 120.27(7) 1_555 1_555 1_555 yes C(2) C(3) C(4) 119.50(5) 1_555 1_555 1_555 yes F(4) C(4) C(3) 120.53(6) 1_555 1_555 1_555 yes F(4) C(4) C(5) 122.24(6) 1_555 1_555 1_555 yes C(3) C(4) C(5) 117.23(5) 1_555 1_555 1_555 yes F(5) C(5) N(1) 117.03(7) 1_555 1_555 1_555 yes F(5) C(5) C(4) 119.01(7) 1_555 1_555 1_555 yes N(1) C(5) C(4) 123.96(6) 1_555 1_555 1_555 yes F(6) C(6) N(2) 116.60(9) 1_555 1_555 1_555 yes F(6) C(6) C(7) 119.39(9) 1_555 1_555 1_555 yes N(2) C(6) C(7) 124.00(7) 1_555 1_555 1_555 yes F(7) C(7) C(6) 121.50(9) 1_555 1_555 1_555 yes F(7) C(7) C(8) 121.05(9) 1_555 1_555 1_555 yes C(6) C(7) C(8) 117.45(7) 1_555 1_555 1_555 yes F(8) C(8) C(7) 120.76(9) 1_555 1_555 1_555 yes F(8) C(8) C(9) 120.27(9) 1_555 1_555 1_555 yes C(7) C(8) C(9) 118.96(7) 1_555 1_555 1_555 yes F(9) C(9) C(8) 121.41(8) 1_555 1_555 1_555 yes F(9) C(9) C(10) 121.20(8) 1_555 1_555 1_555 yes C(8) C(9) C(10) 117.38(6) 1_555 1_555 1_555 yes F(10) C(10) N(2) 116.65(8) 1_555 1_555 1_555 yes F(10) C(10) C(9) 119.22(8) 1_555 1_555 1_555 yes N(2) C(10) C(9) 124.14(7) 1_555 1_555 1_555 yes loop_ _atom_dummy_label _atom_dummy_fract_x _atom_dummy_fract_y _atom_dummy_fract_z DUM0 0 0 0