# Supplementary Material (ESI) for New Journal of Chemistry # This journal is (c) The Royal Society of Chemistry and # The Centre National de la Recherche Scientifique, 2007 data_global _journal_name_full 'New J.Chem.(Nouv.J.Chim.)' _journal_coden_Cambridge 0440 _publ_contact_author_name 'Michel Etienne' _publ_contact_author_address ; Lab Chimie de Coordination CNRS 205 Route de Narbonne Toulouse Cedex 4 31077 FRANCE ; _publ_contact_author_email ETIENNE@LCC-TOULOUSE.FR _publ_section_title ; The structure of fluorinated indazoles: the effect of the replacement of an H by a F atom on the supramolecular structure of NH-indazoles ; _publ_section_references ; Altomare, A., Cascarano, G., Giacovazzo, G., Guagliardi, A., Burla, M.C., Polidori, G. and Camalli, M. (1994)., SIR92 program for automatic solution of crystal structures by direct methods. J. Appl. Cryst. 27, 435. Sheldrick, G. M. (1997). SHELXL97. Program for the refinement of Crystal Structures. University of Gottingen, Germany. Stoe, IPDS Manual. Version 2.75. Stoe & Cie, Darmstadt,1996, Germany. Stoe, X-RED, Data Reduction for STADI4 and IPDS, Revision 1.08. Stoe & Cie, Darmstadt, 1996, Germany. MULTI SCAN - c.f. r.h. blessing, acta cryst. (1995), a51, 33-38 WINGX - 1.63 Integrated System of Windows Programs for the Solution, Refinement and Analysis of Single Crystal X-Ray Diffraction Data. Farrugia, L. J. Appl. Crystallogr., 1999, 32, 837. ORTEP3 for Windows, Farrugia, L. J. J. Appl. Crystallogr. 1997, 30, 565.; ; loop_ _publ_author_name 'Michel Etienne' 'Ibon Alkorta' 'Rosa Claramunt' 'J. Elguero' 'Kane Jacob' 'Concepcion Lopez' ; C.P.Medina ; 'Pascal Oulie' 'Johannes Teichert' 'Laure Vendier' data_1 _database_code_depnum_ccdc_archive 'CCDC 615981' #----------------------------------------------------------------------------# # CHEMICAL INFORMATION # #----------------------------------------------------------------------------# _chemical_name_systematic ; ? ; _chemical_formula_moiety 'C8 H8 N2' _chemical_formula_sum 'C8 H8 N2' _chemical_formula_weight 132.16 _chemical_compound_source 'synthesis as described' #----------------------------------------------------------------------------# # UNIT CELL INFORMATION # #----------------------------------------------------------------------------# _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M 'P 1 21/n 1' _symmetry_space_group_name_Hall '-P 2yn' _symmetry_Int_Tables_number 14 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 8.9070(9) _cell_length_b 5.6894(8) _cell_length_c 13.0599(13) _cell_angle_alpha 90 _cell_angle_beta 90.588(12) _cell_angle_gamma 90 _cell_volume 661.78(13) _cell_formula_units_Z 4 _cell_measurement_temperature 180 _cell_measurement_reflns_used 8000 _cell_measurement_theta_min 1.65 _cell_measurement_theta_max 26.05 _cell_measurement_wavelength 0.71073 #----------------------------------------------------------------------------# # CRYSTAL INFORMATION # #----------------------------------------------------------------------------# _exptl_crystal_description parallelepiped _exptl_crystal_colour colourless _exptl_crystal_size_max 0.15 _exptl_crystal_size_mid 0.15 _exptl_crystal_size_min 0.07 _exptl_crystal_density_diffrn 1.327 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 280 _exptl_special_details ; ? ; #----------------------------------------------------------------------------# # ABSORPTION CORRECTION # #----------------------------------------------------------------------------# _exptl_absorpt_coefficient_mu 0.082 _exptl_absorpt_correction_type refdelf _exptl_absorpt_process_details ; (See: Walker, N. & Stuart, D. (1983) Acta Cryst. A39, 158-166) ; _exptl_absorpt_correction_T_min 0.989 _exptl_absorpt_correction_T_max 0.992 #----------------------------------------------------------------------------# # DATA COLLECTION # #----------------------------------------------------------------------------# _diffrn_ambient_temperature 180 _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device 'Stoe IPDS' _diffrn_measurement_method \f _diffrn_standards_number 200 _diffrn_standards_interval_count ? _diffrn_standards_interval_time 4 _diffrn_standards_decay_% 0.1 _diffrn_reflns_av_R_equivalents 0.0244 _diffrn_reflns_av_unetI/netI 0.0162 _diffrn_reflns_number 4874 _diffrn_reflns_limit_h_min -10 _diffrn_reflns_limit_h_max 10 _diffrn_reflns_limit_k_min -7 _diffrn_reflns_limit_k_max 7 _diffrn_reflns_limit_l_min -16 _diffrn_reflns_limit_l_max 15 _diffrn_reflns_theta_min 3.91 _diffrn_reflns_theta_max 26.03 _diffrn_reflns_theta_full 26.03 _diffrn_measured_fraction_theta_full 0.947 _diffrn_measured_fraction_theta_max 0.947 _reflns_number_total 1224 _reflns_number_gt 1095 _reflns_threshold_expression >2\s(I) #----------------------------------------------------------------------------# # COMPUTER PROGRAMS USED # #----------------------------------------------------------------------------# _computing_data_collection 'Stoe IPDS software (Stoe, 1996)' _computing_cell_refinement 'Stoe IPDS software (Stoe, 1996)' _computing_data_reduction 'XRED (Stoe, 1.08, 1996)' _computing_structure_solution 'SIR92 (Giacovazzo et al, 1993)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Ortep-3 for Windows (Farrugia, 1997)' _computing_publication_material 'WinGX publication routines (Farrugia, 1999)' #----------------------------------------------------------------------------# # REFINEMENT INFORMATION # #----------------------------------------------------------------------------# _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^)+(0.0414P)^2^+0.2704P] 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_number_reflns 1224 _refine_ls_number_parameters 92 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.042 _refine_ls_R_factor_gt 0.0368 _refine_ls_wR_factor_ref 0.0943 _refine_ls_wR_factor_gt 0.091 _refine_ls_goodness_of_fit_ref 1.063 _refine_ls_restrained_S_all 1.063 _refine_ls_shift/su_max 0 _refine_ls_shift/su_mean 0 _refine_diff_density_max 0.185 _refine_diff_density_min -0.225 _refine_diff_density_rms 0.034 #----------------------------------------------------------------------------# # ATOMIC TYPES, COORDINATES AND THERMAL PARAMETERS # #----------------------------------------------------------------------------# 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 0 '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' 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 N1 N 0.49318(13) 0.38551(19) 0.11567(8) 0.0266(3) Uani 1 1 d . . . H1 H 0.4509 0.5185 0.1033 0.032 Uiso 1 1 calc R . . N2 N 0.59043(12) 0.27624(19) 0.05057(8) 0.0258(3) Uani 1 1 d . . . C3A C 0.56302(13) 0.0575(2) 0.19347(9) 0.0219(3) Uani 1 1 d . . . C6 C 0.38817(15) 0.1285(2) 0.36464(10) 0.0280(3) Uani 1 1 d . . . H6 H 0.3301 0.1482 0.4228 0.034 Uiso 1 1 calc R . . C7A C 0.47154(14) 0.2576(2) 0.20261(9) 0.0223(3) Uani 1 1 d . . . C4 C 0.56729(15) -0.1098(2) 0.27256(10) 0.0267(3) Uani 1 1 d . . . H4 H 0.6277 -0.2426 0.2679 0.032 Uiso 1 1 calc R . . C5 C 0.47987(15) -0.0720(2) 0.35689(10) 0.0289(3) Uani 1 1 d . . . H5 H 0.4813 -0.1809 0.41 0.035 Uiso 1 1 calc R . . C8 C 0.74438(15) -0.0829(2) 0.04945(11) 0.0307(3) Uani 1 1 d . . . H8A H 0.7466 -0.0573 -0.0232 0.046 Uiso 1 1 calc R . . H8B H 0.7152 -0.2423 0.0629 0.046 Uiso 1 1 calc R . . H8C H 0.8423 -0.0546 0.0782 0.046 Uiso 1 1 calc R . . C3 C 0.63403(14) 0.0808(2) 0.09660(9) 0.0233(3) Uani 1 1 d . . . C7 C 0.38182(14) 0.2961(2) 0.28878(9) 0.0262(3) Uani 1 1 d . . . H7 H 0.3211 0.4284 0.2943 0.031 Uiso 1 1 calc R . . 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 N1 0.0321(6) 0.0223(6) 0.0254(6) 0.0037(4) 0.0035(5) 0.0060(4) N2 0.0282(6) 0.0265(6) 0.0229(5) 0.0018(4) 0.0028(4) 0.0001(4) C3A 0.0210(6) 0.0221(6) 0.0226(6) -0.0007(5) -0.0018(5) -0.0020(5) C6 0.0266(7) 0.0350(7) 0.0224(6) -0.0020(5) 0.0025(5) -0.0053(5) C7A 0.0228(6) 0.0221(6) 0.0220(6) 0.0011(5) -0.0020(5) -0.0019(5) C4 0.0283(7) 0.0238(7) 0.0281(6) 0.0029(5) -0.0023(5) 0.0008(5) C5 0.0329(7) 0.0296(7) 0.0241(6) 0.0066(5) -0.0015(5) -0.0043(5) C8 0.0309(7) 0.0286(7) 0.0325(7) -0.0009(6) 0.0046(6) 0.0016(5) C3 0.0227(6) 0.0237(6) 0.0235(6) 0.0004(5) -0.0003(5) -0.0024(5) C7 0.0241(7) 0.0282(7) 0.0264(6) -0.0033(5) 0.0000(5) 0.0013(5) #----------------------------------------------------------------------------# # MOLECULAR GEOMETRY # #----------------------------------------------------------------------------# _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 N1 C7A 1.3638(16) . ? N1 N2 1.3693(15) . ? N2 C3 1.3203(16) . ? C3A C4 1.4050(17) . ? C3A C7A 1.4060(17) . ? C3A C3 1.4264(18) . ? C6 C7 1.3762(19) . ? C6 C5 1.4069(19) . ? C7A C7 1.4041(19) . ? C4 C5 1.372(2) . ? C8 C3 1.4919(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 C7A N1 N2 111.75(10) . . ? C3 N2 N1 106.53(10) . . ? C4 C3A C7A 119.85(12) . . ? C4 C3A C3 134.93(12) . . ? C7A C3A C3 105.22(11) . . ? C7 C6 C5 121.98(13) . . ? N1 C7A C7 132.11(12) . . ? N1 C7A C3A 105.92(11) . . ? C7 C7A C3A 121.97(11) . . ? C5 C4 C3A 118.18(12) . . ? C4 C5 C6 121.31(12) . . ? N2 C3 C3A 110.56(11) . . ? N2 C3 C8 121.99(11) . . ? C3A C3 C8 127.44(11) . . ? C6 C7 C7A 116.70(12) . . ? # Attachment 'B617988F_Cpd7.cif' data_2 _database_code_depnum_ccdc_archive 'CCDC 615982' #----------------------------------------------------------------------------# # CHEMICAL INFORMATION # #----------------------------------------------------------------------------# _chemical_name_systematic ; ? ; _chemical_formula_moiety 'C8 H5 F3 N2' _chemical_formula_sum 'C8 H5 F3 N2' _chemical_formula_weight 186.14 _chemical_compound_source 'synthesis as described' _chemical_absolute_configuration unk #----------------------------------------------------------------------------# # UNIT CELL INFORMATION # #----------------------------------------------------------------------------# _symmetry_cell_setting trigonal _symmetry_space_group_name_H-M 'P 32' _symmetry_space_group_name_Hall 'P 32' _symmetry_Int_Tables_number 145 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-y, x-y, z+2/3' '-x+y, -x, z+1/3' _cell_length_a 12.5397(18) _cell_length_b 12.5397(18) _cell_length_c 4.3463(9) _cell_angle_alpha 90 _cell_angle_beta 90 _cell_angle_gamma 120 _cell_volume 591.87(17) _cell_formula_units_Z 3 _cell_measurement_temperature 180 _cell_measurement_reflns_used 3500 _cell_measurement_theta_min 3.2421 _cell_measurement_theta_max 32.1205 _cell_measurement_wavelength 0.71073 #----------------------------------------------------------------------------# # CRYSTAL INFORMATION # #----------------------------------------------------------------------------# _exptl_crystal_description needle _exptl_crystal_colour colourless _exptl_crystal_size_max 0.5 _exptl_crystal_size_mid 0.05 _exptl_crystal_size_min 0.05 _exptl_crystal_density_diffrn 1.567 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 282 _exptl_special_details ; ? ; #----------------------------------------------------------------------------# # ABSORPTION CORRECTION # #----------------------------------------------------------------------------# _exptl_absorpt_coefficient_mu 0.146 _exptl_absorpt_correction_type refdelf _exptl_absorpt_process_details ; (See: Walker, N. & Stuart, D. (1983) Acta Cryst. A39, 158-166) ; _exptl_absorpt_correction_T_min 0.931 _exptl_absorpt_correction_T_max 0.991 #----------------------------------------------------------------------------# # DATA COLLECTION # #----------------------------------------------------------------------------# _diffrn_ambient_temperature 180 _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 'Oxford-Diffraction XCALIBUR' _diffrn_measurement_method \w-\f _diffrn_detector_area_resol_mean ? _diffrn_standards_number 0 _diffrn_standards_interval_count 0 _diffrn_standards_interval_time 0 _diffrn_standards_decay_% 0 _diffrn_reflns_av_R_equivalents 0.1597 _diffrn_reflns_av_unetI/netI 0.1097 _diffrn_reflns_number 6295 _diffrn_reflns_limit_h_min -18 _diffrn_reflns_limit_h_max 17 _diffrn_reflns_limit_k_min -17 _diffrn_reflns_limit_k_max 18 _diffrn_reflns_limit_l_min -6 _diffrn_reflns_limit_l_max 6 _diffrn_reflns_theta_min 3.25 _diffrn_reflns_theta_max 32.13 _diffrn_reflns_theta_full 32.13 _diffrn_measured_fraction_theta_full 0.96 _diffrn_measured_fraction_theta_max 0.96 _reflns_number_total 1329 _reflns_number_gt 861 _reflns_threshold_expression >2\s(I) #----------------------------------------------------------------------------# # COMPUTER PROGRAMS USED # #----------------------------------------------------------------------------# _computing_data_collection 'CrysAlis CCD, Oxford Diffraction Ltd.' _computing_cell_refinement 'CrysAlis RED, Oxford Diffraction Ltd.' _computing_data_reduction 'CrysAlis RED, Oxford Diffraction Ltd.' _computing_structure_solution 'SIR92 (Giacovazzo et al, 1993)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Ortep-3 for Windows (Farrugia, 1997)' _computing_publication_material 'WinGX publication routines (Farrugia, 1999)' #----------------------------------------------------------------------------# # REFINEMENT INFORMATION # #----------------------------------------------------------------------------# _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^)+(0.0697P)^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 constr _refine_ls_extinction_method none _refine_ls_number_reflns 1329 _refine_ls_number_parameters 118 _refine_ls_number_restraints 1 _refine_ls_R_factor_all 0.1277 _refine_ls_R_factor_gt 0.0885 _refine_ls_wR_factor_ref 0.1687 _refine_ls_wR_factor_gt 0.1489 _refine_ls_goodness_of_fit_ref 1.048 _refine_ls_restrained_S_all 1.048 _refine_ls_shift/su_max 0 _refine_ls_shift/su_mean 0 _refine_diff_density_max 0.255 _refine_diff_density_min -0.246 _refine_diff_density_rms 0.065 #----------------------------------------------------------------------------# # ATOMIC TYPES, COORDINATES AND THERMAL PARAMETERS # #----------------------------------------------------------------------------# 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 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0 0 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' F F 0.0171 0 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 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 C3 C 0.3007(4) 0.2101(4) 1.2877(9) 0.0339(9) Uani 1 1 d . . . C8 C 0.3853(4) 0.1758(4) 1.4393(10) 0.0372(9) Uani 1 1 d . . . C7A C 0.2155(4) 0.2971(4) 1.0143(9) 0.0315(8) Uani 1 1 d . . . C3A C 0.3295(4) 0.3209(4) 1.1358(9) 0.0316(8) Uani 1 1 d . . . C4 C 0.4350(4) 0.4364(4) 1.0853(10) 0.0395(10) Uani 1 1 d . . . H4 H 0.5111 0.4545 1.1646 0.047 Uiso 1 1 calc R . . C5 C 0.4221(5) 0.5210(5) 0.9161(12) 0.0447(11) Uani 1 1 d . . . H5 H 0.4906 0.5983 0.8834 0.054 Uiso 1 1 calc R . . C6 C 0.3084(5) 0.4945(5) 0.7901(11) 0.0444(11) Uani 1 1 d . . . H6 H 0.3042 0.5539 0.6708 0.053 Uiso 1 1 calc R . . C7 C 0.2038(5) 0.3840(4) 0.8380(10) 0.0415(10) Uani 1 1 d . . . H7 H 0.1283 0.3674 0.7571 0.05 Uiso 1 1 calc R . . N2 N 0.1820(3) 0.1263(3) 1.2641(8) 0.0364(8) Uani 1 1 d . . . N1 N 0.1314(3) 0.1810(3) 1.0971(9) 0.0377(8) Uani 1 1 d . . . H1 H 0.0546 0.1459 1.0493 0.045 Uiso 1 1 calc R . . F2 F 0.4742(3) 0.2680(3) 1.5933(7) 0.0582(9) Uani 1 1 d . . . F3 F 0.4389(3) 0.1367(4) 1.2422(6) 0.0687(11) Uani 1 1 d . . . F1 F 0.3260(3) 0.0841(3) 1.6400(7) 0.0646(9) 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 C3 0.032(2) 0.035(2) 0.0337(19) -0.0014(16) 0.0013(16) 0.0164(18) C8 0.041(2) 0.041(2) 0.0327(18) -0.0037(17) -0.0048(17) 0.023(2) C7A 0.028(2) 0.030(2) 0.037(2) -0.0027(15) 0.0020(15) 0.0147(18) C3A 0.0282(19) 0.031(2) 0.0349(17) -0.0035(16) 0.0020(15) 0.0139(17) C4 0.033(2) 0.032(2) 0.048(2) -0.0038(18) 0.0033(19) 0.0129(18) C5 0.044(3) 0.032(2) 0.053(3) 0.0030(19) 0.011(2) 0.016(2) C6 0.058(3) 0.042(3) 0.044(2) 0.0089(19) 0.012(2) 0.033(3) C7 0.046(3) 0.041(3) 0.047(2) 0.0031(19) 0.0053(19) 0.028(2) N2 0.0345(19) 0.0306(19) 0.045(2) 0.0013(14) 0.0001(15) 0.0169(16) N1 0.0277(18) 0.0294(18) 0.056(2) -0.0005(15) -0.0043(16) 0.0146(15) F2 0.0450(16) 0.062(2) 0.067(2) -0.0132(16) -0.0187(14) 0.0256(16) F3 0.090(3) 0.119(3) 0.0444(16) -0.0114(17) -0.0071(15) 0.088(3) F1 0.064(2) 0.067(2) 0.0606(18) 0.0201(16) -0.0043(15) 0.0312(18) #----------------------------------------------------------------------------# # MOLECULAR GEOMETRY # #----------------------------------------------------------------------------# _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 C3 N2 1.329(6) . ? C3 C3A 1.413(6) . ? C3 C8 1.483(6) . ? C8 F2 1.319(5) . ? C8 F3 1.325(5) . ? C8 F1 1.334(6) . ? C7A N1 1.352(5) . ? C7A C7 1.398(6) . ? C7A C3A 1.410(6) . ? C3A C4 1.407(6) . ? C4 C5 1.365(7) . ? C5 C6 1.404(8) . ? C6 C7 1.366(7) . ? N2 N1 1.355(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 N2 C3 C3A 112.1(4) . . ? N2 C3 C8 119.1(4) . . ? C3A C3 C8 128.7(4) . . ? F2 C8 F3 106.8(4) . . ? F2 C8 F1 106.6(4) . . ? F3 C8 F1 105.7(4) . . ? F2 C8 C3 112.7(4) . . ? F3 C8 C3 112.9(4) . . ? F1 C8 C3 111.6(4) . . ? N1 C7A C7 131.0(4) . . ? N1 C7A C3A 106.9(3) . . ? C7 C7A C3A 122.1(4) . . ? C4 C3A C7A 119.4(4) . . ? C4 C3A C3 137.0(4) . . ? C7A C3A C3 103.5(4) . . ? C5 C4 C3A 117.9(4) . . ? C4 C5 C6 121.8(5) . . ? C7 C6 C5 121.8(4) . . ? C6 C7 C7A 116.9(4) . . ? C3 N2 N1 105.3(4) . . ? C7A N1 N2 112.2(4) . . ? # Attachment 'B617988F_Cpd9.cif' data_3 _database_code_depnum_ccdc_archive 'CCDC 615983' #----------------------------------------------------------------------------# # CHEMICAL INFORMATION # #----------------------------------------------------------------------------# _chemical_name_systematic ; ? ; _chemical_formula_moiety 'C8 H1 F7 N2' _chemical_formula_sum 'C8 H F7 N2' _chemical_formula_weight 258.11 _chemical_compound_source 'synthesis as described' _chemical_absolute_configuration unk #----------------------------------------------------------------------------# # UNIT CELL INFORMATION # #----------------------------------------------------------------------------# _symmetry_cell_setting trigonal _symmetry_space_group_name_H-M 'P 32' _symmetry_space_group_name_Hall 'P 32' _symmetry_Int_Tables_number 145 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-y, x-y, z+2/3' '-x+y, -x, z+1/3' _cell_length_a 12.5382(18) _cell_length_b 12.5382(18) _cell_length_c 4.9499(10) _cell_angle_alpha 90 _cell_angle_beta 90 _cell_angle_gamma 120 _cell_volume 673.90(19) _cell_formula_units_Z 3 _cell_measurement_temperature 180 _cell_measurement_reflns_used 1650 _cell_measurement_theta_min 3.24 _cell_measurement_theta_max 32.1231 _cell_measurement_wavelength 0.71073 #----------------------------------------------------------------------------# # CRYSTAL INFORMATION # #----------------------------------------------------------------------------# _exptl_crystal_description stick _exptl_crystal_colour colourless _exptl_crystal_size_max 0.35 _exptl_crystal_size_mid 0.15 _exptl_crystal_size_min 0.1 _exptl_crystal_density_diffrn 1.908 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 378 _exptl_special_details ; ? ; #----------------------------------------------------------------------------# # ABSORPTION CORRECTION # #----------------------------------------------------------------------------# _exptl_absorpt_coefficient_mu 0.219 _exptl_absorpt_correction_type refdelf _exptl_absorpt_process_details ; (See: Walker, N. & Stuart, D. (1983) Acta Cryst. A39, 158-166) ; _exptl_absorpt_correction_T_min 0.928 _exptl_absorpt_correction_T_max 0.974 #----------------------------------------------------------------------------# # DATA COLLECTION # #----------------------------------------------------------------------------# _diffrn_ambient_temperature 180 _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 'Oxford-Diffraction XCALIBUR' _diffrn_measurement_method \w-\f _diffrn_detector_area_resol_mean ? _diffrn_standards_number 0 _diffrn_standards_interval_count 0 _diffrn_standards_interval_time 0 _diffrn_standards_decay_% 0 _diffrn_reflns_av_R_equivalents 0.0828 _diffrn_reflns_av_unetI/netI 0.0946 _diffrn_reflns_number 7260 _diffrn_reflns_limit_h_min -18 _diffrn_reflns_limit_h_max 18 _diffrn_reflns_limit_k_min -17 _diffrn_reflns_limit_k_max 18 _diffrn_reflns_limit_l_min -7 _diffrn_reflns_limit_l_max 6 _diffrn_reflns_theta_min 3.25 _diffrn_reflns_theta_max 32.14 _diffrn_reflns_theta_full 32.14 _diffrn_measured_fraction_theta_full 0.959 _diffrn_measured_fraction_theta_max 0.959 _reflns_number_total 1520 _reflns_number_gt 694 _reflns_threshold_expression >2\s(I) #----------------------------------------------------------------------------# # COMPUTER PROGRAMS USED # #----------------------------------------------------------------------------# _computing_data_collection 'CrysAlis CCD, Oxford Diffraction Ltd.' _computing_cell_refinement 'CrysAlis RED, Oxford Diffraction Ltd.' _computing_data_reduction 'CrysAlis RED, Oxford Diffraction Ltd.' _computing_structure_solution 'SIR92 (Giacovazzo et al, 1993)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Ortep-3 for Windows (Farrugia, 1997)' _computing_publication_material 'WinGX publication routines (Farrugia, 1999)' #----------------------------------------------------------------------------# # REFINEMENT INFORMATION # #----------------------------------------------------------------------------# _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^)+(0.0324P)^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 constr _refine_ls_extinction_method none _refine_ls_number_reflns 1520 _refine_ls_number_parameters 154 _refine_ls_number_restraints 1 _refine_ls_R_factor_all 0.1385 _refine_ls_R_factor_gt 0.0418 _refine_ls_wR_factor_ref 0.0934 _refine_ls_wR_factor_gt 0.0713 _refine_ls_goodness_of_fit_ref 0.92 _refine_ls_restrained_S_all 0.92 _refine_ls_shift/su_max 0 _refine_ls_shift/su_mean 0 _refine_diff_density_max 0.177 _refine_diff_density_min -0.206 _refine_diff_density_rms 0.045 #----------------------------------------------------------------------------# # ATOMIC TYPES, COORDINATES AND THERMAL PARAMETERS # #----------------------------------------------------------------------------# 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 0 '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' 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 C3 C 0.2938(4) 0.2177(4) 1.2547(8) 0.0372(9) Uani 1 1 d . . . C3A C 0.3236(3) 0.3207(3) 1.0923(8) 0.0335(8) Uani 1 1 d . . . C4 C 0.4281(4) 0.4350(4) 1.0308(9) 0.0410(10) Uani 1 1 d . . . C5 C 0.4212(4) 0.5098(4) 0.8455(8) 0.0440(10) Uani 1 1 d . . . C6 C 0.3095(4) 0.4737(4) 0.7063(9) 0.0427(10) Uani 1 1 d . . . C7 C 0.2061(4) 0.3661(4) 0.7612(8) 0.0422(10) Uani 1 1 d . . . C7A C 0.2126(3) 0.2893(3) 0.9554(8) 0.0359(9) Uani 1 1 d . . . C8 C 0.3750(4) 0.1901(4) 1.4260(10) 0.0425(9) Uani 1 1 d . . . N1 N 0.1273(3) 0.1761(3) 1.0439(7) 0.0439(9) Uani 1 1 d . . . H1 H 0.0518 0.1375 0.9911 0.053 Uiso 1 1 calc R . . N2 N 0.1758(3) 0.1311(3) 1.2272(7) 0.0427(8) Uani 1 1 d . . . F1 F 0.3106(2) 0.0981(3) 1.5975(5) 0.0735(9) Uani 1 1 d . . . F2 F 0.4514(2) 0.2874(2) 1.5753(5) 0.0602(7) Uani 1 1 d . . . F3 F 0.4446(3) 0.1608(3) 1.2786(5) 0.0645(8) Uani 1 1 d . . . F4 F 0.5359(2) 0.4681(2) 1.1565(5) 0.0564(7) Uani 1 1 d . . . F5 F 0.5191(2) 0.6189(2) 0.7810(5) 0.0614(7) Uani 1 1 d . . . F6 F 0.3102(2) 0.5519(2) 0.5172(5) 0.0587(7) Uani 1 1 d . . . F7 F 0.1001(2) 0.3317(2) 0.6290(5) 0.0612(7) 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 C3 0.036(2) 0.035(2) 0.042(2) -0.0007(18) 0.0047(18) 0.0182(18) C3A 0.036(2) 0.0322(19) 0.037(2) -0.0003(17) 0.0071(17) 0.0205(18) C4 0.033(2) 0.038(2) 0.049(3) -0.005(2) 0.0009(19) 0.0155(19) C5 0.046(2) 0.030(2) 0.052(3) 0.007(2) 0.014(2) 0.016(2) C6 0.057(3) 0.040(2) 0.039(2) 0.002(2) 0.003(2) 0.030(2) C7 0.045(2) 0.049(3) 0.042(3) 0.003(2) 0.0001(19) 0.030(2) C7A 0.036(2) 0.031(2) 0.045(3) -0.0017(19) 0.0030(18) 0.0194(18) C8 0.043(2) 0.045(3) 0.045(2) 0.004(2) 0.006(2) 0.026(2) N1 0.0341(19) 0.041(2) 0.057(2) 0.0017(16) -0.0050(17) 0.0190(16) N2 0.042(2) 0.0375(18) 0.053(2) 0.0004(17) -0.0023(17) 0.0231(17) F1 0.0621(18) 0.0719(19) 0.084(2) 0.0363(16) 0.0009(15) 0.0316(15) F2 0.0648(17) 0.0649(18) 0.0594(17) -0.0143(14) -0.0198(14) 0.0388(15) F3 0.0705(18) 0.085(2) 0.0655(18) -0.0083(15) -0.0023(14) 0.0598(18) F4 0.0344(13) 0.0512(15) 0.0698(18) 0.0066(13) -0.0060(12) 0.0111(11) F5 0.0580(17) 0.0407(14) 0.0742(18) 0.0102(13) 0.0144(14) 0.0161(13) F6 0.0769(18) 0.0561(15) 0.0538(16) 0.0152(13) 0.0076(13) 0.0413(15) F7 0.0568(16) 0.0670(17) 0.0641(17) 0.0036(14) -0.0156(13) 0.0342(15) #----------------------------------------------------------------------------# # MOLECULAR GEOMETRY # #----------------------------------------------------------------------------# _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 C3 N2 1.334(5) . ? C3 C3A 1.405(6) . ? C3 C8 1.492(6) . ? C3A C4 1.409(5) . ? C3A C7A 1.415(6) . ? C4 C5 1.346(5) . ? C4 F4 1.351(5) . ? C5 F5 1.342(5) . ? C5 C6 1.417(6) . ? C6 C7 1.351(5) . ? C6 F6 1.352(5) . ? C7 F7 1.345(4) . ? C7 C7A 1.391(5) . ? C7A N1 1.353(5) . ? C8 F3 1.323(5) . ? C8 F1 1.331(5) . ? C8 F2 1.336(5) . ? N1 N2 1.362(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 N2 C3 C3A 111.5(4) . . ? N2 C3 C8 118.5(4) . . ? C3A C3 C8 129.8(4) . . ? C3 C3A C4 138.0(4) . . ? C3 C3A C7A 104.2(3) . . ? C4 C3A C7A 117.7(4) . . ? C5 C4 F4 120.2(3) . . ? C5 C4 C3A 120.3(4) . . ? F4 C4 C3A 119.5(4) . . ? F5 C5 C4 121.9(4) . . ? F5 C5 C6 117.6(4) . . ? C4 C5 C6 120.5(4) . . ? C7 C6 F6 121.3(4) . . ? C7 C6 C5 121.5(4) . . ? F6 C6 C5 117.3(4) . . ? F7 C7 C6 121.5(4) . . ? F7 C7 C7A 120.3(4) . . ? C6 C7 C7A 118.1(4) . . ? N1 C7A C7 131.3(4) . . ? N1 C7A C3A 106.8(3) . . ? C7 C7A C3A 121.8(4) . . ? F3 C8 F1 108.0(3) . . ? F3 C8 F2 106.7(3) . . ? F1 C8 F2 106.6(4) . . ? F3 C8 C3 111.9(4) . . ? F1 C8 C3 112.0(3) . . ? F2 C8 C3 111.3(3) . . ? C7A N1 N2 111.6(3) . . ? C3 N2 N1 105.9(3) . . ?