Electronic Supplementary Material for CrystEngComm This journal is (c) The Royal Society of Chemistry 2007 data_global _journal_name_full CrystEngComm #=============================================================================== # 2. PROCESSING SUMMARY (JOURNAL OFFICE ONLY) _journal_coden_Cambridge 1350 #============================================================================== # 0. AUDIT DETAILS _audit_creation_date 'Jan 21 14:33:58 2005' _audit_creation_method 'PLATON option' _audit_update_record ; ? ; #=============================================================================== # 1. SUBMISSION DETAILS _publ_contact_author_name 'Tayur Guru Row' _publ_contact_author_address # address of author for correspondence ; Indian Institute of Science Bangalore Karnataka 560012 INDIA ; _publ_contact_author_email SSCTNG@SSCU.IISC.ERNET.IN _journal_year ? _journal_volume ? _journal_issue ? _journal_page_first ? _journal_page_last ? #=============================================================================== # 3. TITLE AND AUTHOR LIST _publ_section_title ; Evaluation of Interchangeability of C-H and C-F groups: Insights from Crystal Packing in a series of isomeric Fluorinated Benzanilides. ; _publ_section_title_footnote ; ? ; #=============================================================================== # 4. TEXT _publ_section_synopsis ; ? ; _publ_section_abstract ; ? ; # Insert blank lines between paragraphs _publ_section_comment ; ? ; _publ_section_exptl_prep ; ? ; _publ_section_exptl_refinement ; ? ; # Insert blank lines between references _publ_section_references ; Allen, F.H. & Kennard, O. (1993). Chem. Des. Autom. News., 8, 31-37. Altomare, A., Burla, M.C., Camalli, M., Cascarano, G.L., Giacovazzo, C. Guagliardi, A., Moliterni, A.G.G., Polidori, G. & Spagna, R. (1999) J. Appl. Cryst. 32, 115-119. Beurskens, P.T., Admiraal, G., Beurskens, G., Bosman, W.P., Garc\'ia-Granda, S., Gould, R.O., Smits, J.M.M. & Smykalla, C. (1999) The DIRDIF99 program system, Technical Report of the Crystallography Laboratory, University of Nijmegen, The Netherlands. Boer, J.L. de & Duisenberg, A.J.M. (1984). Acta Cryst. A40, C-410. Boeyens, J.C.A. (1978). J.Cryst.Mol.Struct. 8, 317-320. Cremer, D. & Pople, J.A. (1975). J. Am. Chem. Soc. 97, 1354-1358. Enraf-Nonius (1989). CAD-4 Software. Version 5. Enraf-Nonius, Delft, The Netherlands. Flack, H.D. (1983). Acta Cryst. A39, 876-881. LePage, Y. (1987). J. Appl. Cryst. 20, 264-269. Mackay, A.L. (1984). Acta Cryst. A40, 165-166. Meulenaer, J. de & Tompa, H. (1965). Acta Cryst. 19, 1014-1018. Nonius (1998). Collect Software, Nonius, Delft, The Netherlands. North, A.C.T., Phillips, D.C. & Mathews, F.S. (1968). Acta Cryst. A24, 351-359. Otwinowski, Z. & Minor, W. (1997). Methods in Enzymology, 276, 307-326. Sheldrick, G.M. SHELXL93. Program for crystal structure refinement. University of G\\"ottingen, Germany, 1993. Sheldrick, G.M. SHELXL97. Program for crystal structure refinement. University of G\\"ottingen, Germany, 1997. Sheldrick, G.M. SHELXS86. Program for Crystal Structure solution. University of G\\"ottingen, Germany, 1986. Sheldrick, G.M. SHELXS97. Program for Crystal Structure solution. University of G\\"ottingen, Germany, 1997. Spek, A.L. (1987). Acta Cryst. C43, 1233-1235. Spek, A.L. (1988). J. Appl. Cryst. 21, 578-579. Spek, A.L. (1990). Acta Cryst. A46, C-34. Spek, A.L. (1997). HELENA, Program for Datareduction, Utrecht University, The Netherlands. Spek, A.L. (1994). Am. Crystallogr. Assoc.-Abstracts, 22, 66. Wilson, A.J.C. (1992) Ed. International Tables for Crystallography, Volume C, Kluwer Academic Publishers, Dordrecht, The Netherlands. ; _publ_section_acknowledgements ; ? ; _publ_section_figure_captions ; View of the title compound with the atom numbering scheme. Displacement ellipsoids for non-H atoms are drawn at the 50% probability level. ; loop_ _publ_author_name 'Tayur Guru Row' 'Deepak Chopra' data_dc4_2n_m _database_code_depnum_ccdc_archive 'CCDC 285374' #=============================================================================== # 5. CHEMICAL DATA _chemical_name_systematic ; ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C13 H9 F N O' # Ex: 'C12 H16 N2 O6, H2 O' and '(Cd 2+)3, (C6 N6 Cr 3-)2, 2(H2 O)' _chemical_formula_structural ? _chemical_formula_sum 'C13 H9 F N O' _chemical_formula_iupac ? _chemical_formula_weight 214.21 _chemical_compound_source ? loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source O O 0.0106 0.0060 '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' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' #=============================================================================== # 6. CRYSTAL DATA _symmetry_cell_setting Monoclinic _symmetry_space_group_name_Hall '-P 2ybc' _symmetry_space_group_name_H-M 'P 21/c' _symmetry_Int_Tables_number 14 loop_ _symmetry_equiv_pos_site_id _symmetry_equiv_pos_as_xyz 1 x,y,z 2 -x,1/2+y,1/2-z 3 -x,-y,-z 4 x,1/2-y,1/2+z _cell_length_a 8.0355(18) _cell_length_b 5.3598(12) _cell_length_c 23.640(5) _cell_angle_alpha 90 _cell_angle_beta 90.074(4) _cell_angle_gamma 90 _cell_volume 1018.2(4) _cell_formula_units_Z 4 _cell_measurement_temperature 290(2) _cell_measurement_reflns_used 935 _cell_measurement_theta_min 1.4 _cell_measurement_theta_max 27.4 _cell_special_details ; ; _exptl_crystal_description block _exptl_crystal_colour ' colorless' _exptl_crystal_size_max 0.41 _exptl_crystal_size_mid 0.36 _exptl_crystal_size_min 0.09 _exptl_crystal_size_rad ? _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.397 _exptl_crystal_density_method 'Not Measured' _exptl_crystal_F_000 444 _exptl_absorpt_coefficient_mu 0.102 _exptl_crystal_density_meas_temp ? # Permitted for _exptl_absorpt_correction_type : # analytical 'analytical from crystal shape' # Example: de Meulenaer&Tompa: ABST # cylinder 'cylindrical' # gaussian 'Gaussian from crystal shape' # Example: PLATON/ABSG # integration 'integration from crystal shape' # multi-scan 'symmetry-related measurements' # Example: SADABS, MULABS # none 'no absorption corr. applied' # numerical 'numerical from crystal shape' # psi-scan 'psi-scan corrections' # Example: PLATON/ABSP # refdelf 'refined from delta-F' # Example: SHELXA, DIFABS, DELABS # sphere 'spherical' # Example: PLATON/ABSS _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details '(SADABS; Sheldrick, 1996)' _exptl_absorpt_correction_T_min 0.9415 _exptl_absorpt_correction_T_max 0.9910 #=============================================================================== # 7. EXPERIMENTAL DATA _exptl_special_details ; ; _diffrn_ambient_temperature 290(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 'Bruker SMART APEX CCD area detector' _diffrn_measurement_method '\f and \w scans' _diffrn_detector_area_resol_mean ? # number of measured reflections (redundant set) _diffrn_reflns_number 6666 _diffrn_reflns_av_R_equivalents 0.0241 _diffrn_reflns_av_sigmaI/netI 0.0222 _diffrn_reflns_limit_h_min -9 _diffrn_reflns_limit_h_max 9 _diffrn_reflns_limit_k_min -6 _diffrn_reflns_limit_k_max 6 _diffrn_reflns_limit_l_min -28 _diffrn_reflns_limit_l_max 28 _diffrn_reflns_theta_min 1.72 _diffrn_reflns_theta_max 25.00 _diffrn_measured_fraction_theta_max 0.977 _diffrn_reflns_theta_full 25.00 _diffrn_measured_fraction_theta_full 0.977 _diffrn_reflns_reduction_process ; ; _reflns_number_total 1761 _reflns_number_gt 1523 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'SMART (Bruker, 1998)' _computing_cell_refinement SMART _computing_data_reduction 'SAINT (Bruker, 1998)' _computing_structure_solution 'SIR92 (Altomare et al., 1993)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Ortep-3 for Windows (Farrugia, 1997) and CAMERON (Watkin et al., 1993)' _computing_publication_material 'PLATON (Spek, 2003)' #=============================================================================== # 8. REFINEMENT DATA _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^)+(0.0551P)^2^+0.4798P] 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_number_reflns 1761 _refine_ls_number_parameters 168 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0706 _refine_ls_R_factor_gt 0.0605 _refine_ls_wR_factor_ref 0.1417 _refine_ls_wR_factor_gt 0.1361 _refine_ls_goodness_of_fit_ref 1.132 _refine_ls_restrained_S_all 1.132 _refine_ls_shift/su_max 0.001 _refine_ls_shift/su_mean 0.000 _refine_diff_density_max 0.243 _refine_diff_density_min -0.155 _refine_diff_density_rms 0.041 #=============================================================================== # 9. ATOMIC COORDINATES AND DISPLACEMENT PARAMETERS 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 C13 C 0.2604(3) 0.4083(6) 1.01651(14) 0.0394(9) Uani 0.824(9) 1 d P A 1 N1 N 0.2321(3) 0.2088(5) 0.98143(11) 0.0401(10) Uani 0.824(9) 1 d P A 1 F1 F 0.2888(2) 0.6224(4) 1.21326(7) 0.0633(6) Uani 0.806(4) 1 d P B 1 F1A F 0.2090(13) 0.5300(19) 0.7899(4) 0.095(4) Uani 0.194(4) 1 d P B 2 N1A N 0.2714(17) 0.210(3) 1.0228(8) 0.068(6) Uiso 0.176(9) 1 d P A 2 C13A C 0.240(2) 0.389(4) 0.9857(9) 0.057(5) Uiso 0.176(9) 1 d P A 2 O1 O 0.2439(2) 0.6226(3) 1.00083(6) 0.0621(6) Uani 1 1 d . . . C9 C 0.1830(3) 0.4007(5) 0.83131(10) 0.0523(6) Uani 1 1 d . . . C3 C 0.3253(3) 0.4582(4) 1.17149(9) 0.0470(6) Uani 1 1 d . . . C12 C 0.0865(3) 0.0311(5) 0.90450(11) 0.0547(7) Uani 1 1 d . A . H12 H 0.0533 -0.0950 0.9290 0.066 Uiso 1 1 calc R . . C6 C 0.4093(3) 0.1261(5) 1.08941(11) 0.0566(7) Uani 1 1 d . . . H6 H 0.4376 0.0115 1.0615 0.068 Uiso 1 1 calc R A 2 C4 C 0.4187(3) 0.2564(5) 1.18642(10) 0.0545(7) Uani 1 1 d . A . H4 H 0.4527 0.2325 1.2237 0.065 Uiso 1 1 calc R . . C2 C 0.2736(3) 0.5013(5) 1.11738(9) 0.0483(6) Uani 1 1 d . A . H2 H 0.2110 0.6423 1.1088 0.058 Uiso 1 1 calc R . . C11 C 0.0409(3) 0.0220(5) 0.84887(12) 0.0608(7) Uani 1 1 d . . . H11 H -0.0233 -0.1104 0.8358 0.073 Uiso 1 1 calc R B . C8 C 0.2299(3) 0.4155(4) 0.88747(10) 0.0503(6) Uani 1 1 d . A . H8 H 0.2926 0.5498 0.9004 0.060 Uiso 1 1 calc R . . C10 C 0.0889(3) 0.2057(5) 0.81211(10) 0.0570(7) Uani 1 1 d . B . H10 H 0.0575 0.1980 0.7743 0.068 Uiso 1 1 calc R . . C7 C 0.1817(3) 0.2264(5) 0.92452(9) 0.0465(6) Uani 1 1 d . . . C5 C 0.4616(3) 0.0882(5) 1.14455(12) 0.0607(7) Uani 1 1 d . A . H5 H 0.5257 -0.0508 1.1535 0.073 Uiso 1 1 calc R . . C1 C 0.3152(3) 0.3336(5) 1.07564(10) 0.0482(6) Uani 1 1 d . A . H1N H 0.239(3) 0.066(6) 0.9966(12) 0.058(8) 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 C13 0.0476(16) 0.0333(18) 0.0373(18) 0.0037(13) -0.0002(12) 0.0020(11) N1 0.0526(14) 0.0315(18) 0.0362(15) 0.0022(10) -0.0050(10) -0.0002(10) F1 0.0813(13) 0.0705(12) 0.0381(10) -0.0124(8) -0.0055(8) 0.0030(10) F1A 0.111(8) 0.080(7) 0.094(7) 0.021(5) 0.015(6) -0.010(6) O1 0.1086(16) 0.0331(10) 0.0445(10) 0.0024(7) -0.0131(9) 0.0038(9) C9 0.0629(16) 0.0519(15) 0.0420(13) 0.0042(12) 0.0011(11) 0.0097(12) C3 0.0547(14) 0.0491(14) 0.0374(12) -0.0027(10) -0.0035(10) -0.0080(11) C12 0.0499(14) 0.0473(14) 0.0670(17) 0.0113(12) 0.0022(12) -0.0016(11) C6 0.0568(15) 0.0542(15) 0.0587(16) -0.0126(12) 0.0051(12) -0.0064(12) C4 0.0549(15) 0.0632(16) 0.0455(13) 0.0113(12) -0.0113(11) -0.0082(12) C2 0.0498(14) 0.0526(14) 0.0426(13) 0.0052(11) -0.0040(10) 0.0041(11) C11 0.0616(16) 0.0515(15) 0.0691(18) -0.0114(13) -0.0125(13) -0.0008(12) C8 0.0550(14) 0.0466(13) 0.0492(14) -0.0059(11) 0.0011(11) -0.0065(11) C10 0.0610(16) 0.0653(17) 0.0447(13) -0.0070(12) -0.0099(11) 0.0118(13) C7 0.0421(12) 0.0607(15) 0.0367(12) 0.0023(11) 0.0002(9) 0.0082(11) C5 0.0530(15) 0.0484(15) 0.0807(19) 0.0150(14) -0.0040(13) 0.0057(12) C1 0.0411(12) 0.0604(15) 0.0429(13) -0.0007(11) -0.0028(10) -0.0054(11) #=============================================================================== # 10. 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 C13 O1 1.214(3) . ? C13 N1 1.372(5) . ? C13 C1 1.519(4) . ? N1 C7 1.407(3) . ? N1 H1N 0.85(3) . ? F1 C3 1.355(3) . ? F1A C9 1.217(9) . ? N1A C13A 1.32(3) . ? N1A C1 1.456(18) . ? N1A C6 1.976(18) . ? N1A H1N 1.02(3) . ? C13A O1 1.30(2) . ? C9 C10 1.368(4) . ? C9 C8 1.382(3) . ? C3 C4 1.363(3) . ? C3 C2 1.364(3) . ? C12 C11 1.365(4) . ? C12 C7 1.380(3) . ? C12 H12 0.9300 . ? C6 C1 1.384(4) . ? C6 C5 1.384(4) . ? C6 H6 0.9300 . ? C4 C5 1.383(4) . ? C4 H4 0.9300 . ? C2 C1 1.376(3) . ? C2 H2 0.9300 . ? C11 C10 1.369(4) . ? C11 H11 0.9300 . ? C8 C7 1.395(3) . ? C8 H8 0.9300 . ? C10 H10 0.9300 . ? C5 H5 0.9300 . ? 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 C13 N1 122.3(3) . . ? O1 C13 C1 124.2(3) . . ? N1 C13 C1 113.5(2) . . ? C13 N1 C7 125.0(3) . . ? C13 N1 H1N 116.0(18) . . ? C7 N1 H1N 118.9(19) . . ? C13A N1A C1 106.7(16) . . ? C13A N1A C6 143.1(15) . . ? C13A N1A H1N 95(2) . . ? C1 N1A H1N 157(2) . . ? C6 N1A H1N 117(2) . . ? O1 C13A N1A 121(2) . . ? O1 C13A C7 135.2(16) . . ? N1A C13A C7 103.9(16) . . ? F1A C9 C10 105.3(6) . . ? F1A C9 C8 133.9(6) . . ? C10 C9 C8 120.8(2) . . ? F1 C3 C4 116.5(2) . . ? F1 C3 C2 120.5(2) . . ? C4 C3 C2 123.0(2) . . ? C11 C12 C7 120.4(2) . . ? C11 C12 H12 119.8 . . ? C7 C12 H12 119.8 . . ? C1 C6 C5 120.3(2) . . ? C1 C6 N1A 47.4(5) . . ? C5 C6 N1A 162.3(5) . . ? C1 C6 H6 119.8 . . ? C5 C6 H6 119.8 . . ? N1A C6 H6 73.9 . . ? C3 C4 C5 118.0(2) . . ? C3 C4 H4 121.0 . . ? C5 C4 H4 121.0 . . ? C3 C2 C1 119.2(2) . . ? C3 C2 H2 120.4 . . ? C1 C2 H2 120.4 . . ? C12 C11 C10 120.7(2) . . ? C12 C11 H11 119.7 . . ? C10 C11 H11 119.7 . . ? C9 C8 C7 119.1(2) . . ? C9 C8 H8 120.5 . . ? C7 C8 H8 120.5 . . ? C9 C10 C11 119.7(2) . . ? C9 C10 H10 120.2 . . ? C11 C10 H10 120.2 . . ? C12 C7 C8 119.3(2) . . ? C12 C7 N1 115.8(2) . . ? C8 C7 N1 124.7(2) . . ? C12 C7 C13A 143.9(7) . . ? C4 C5 C6 120.2(2) . . ? C4 C5 H5 119.9 . . ? C6 C5 H5 119.9 . . ? C2 C1 C6 119.3(2) . . ? C2 C1 C13 114.7(2) . . ? C6 C1 C13 125.9(2) . . ? 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 O1 C13 N1 C7 0.0(4) . . . . ? C1 C13 N1 C7 -179.4(2) . . . . ? C1 N1A C13A O1 -3.3(19) . . . . ? C6 N1A C13A O1 -36(3) . . . . ? C1 N1A C13A C7 -178.0(8) . . . . ? C6 N1A C13A C7 149.6(16) . . . . ? N1 C13 O1 C13A -3.9(13) . . . . ? C1 C13 O1 C13A 175.4(15) . . . . ? N1A C13A O1 C13 -0.5(8) . . . . ? C7 C13A O1 C13 172(3) . . . . ? C13A N1A C6 C1 47(2) . . . . ? C13A N1A C6 C5 98(2) . . . . ? C1 N1A C6 C5 51.0(19) . . . . ? F1 C3 C4 C5 -178.5(2) . . . . ? C2 C3 C4 C5 -0.4(4) . . . . ? F1 C3 C2 C1 178.8(2) . . . . ? C4 C3 C2 C1 0.7(4) . . . . ? C7 C12 C11 C10 0.1(4) . . . . ? F1A C9 C8 C7 -177.9(7) . . . . ? C10 C9 C8 C7 0.9(4) . . . . ? F1A C9 C10 C11 178.8(6) . . . . ? C8 C9 C10 C11 -0.3(4) . . . . ? C12 C11 C10 C9 -0.1(4) . . . . ? C11 C12 C7 C8 0.5(4) . . . . ? C11 C12 C7 N1 -175.5(2) . . . . ? C11 C12 C7 C13A 159.4(11) . . . . ? C9 C8 C7 C12 -1.0(3) . . . . ? C9 C8 C7 N1 174.7(2) . . . . ? C9 C8 C7 C13A -168.7(6) . . . . ? C13 N1 C7 C12 -150.2(2) . . . . ? C13 N1 C7 C8 33.9(4) . . . . ? C13 N1 C7 C13A 3.0(10) . . . . ? O1 C13A C7 C12 -129.3(15) . . . . ? N1A C13A C7 C12 44.3(17) . . . . ? O1 C13A C7 C8 32.4(17) . . . . ? N1A C13A C7 C8 -154.1(10) . . . . ? O1 C13A C7 N1 -173(2) . . . . ? N1A C13A C7 N1 0.8(6) . . . . ? C3 C4 C5 C6 -0.3(4) . . . . ? C1 C6 C5 C4 0.6(4) . . . . ? N1A C6 C5 C4 -40.9(18) . . . . ? C3 C2 C1 C6 -0.4(3) . . . . ? C3 C2 C1 N1A 147.5(13) . . . . ? C3 C2 C1 C13 -176.4(2) . . . . ? C5 C6 C1 C2 -0.3(4) . . . . ? N1A C6 C1 C2 163.9(6) . . . . ? C5 C6 C1 N1A -164.2(6) . . . . ? C5 C6 C1 C13 175.3(2) . . . . ? N1A C6 C1 C13 -20.6(6) . . . . ? C13A N1A C1 C2 55.0(18) . . . . ? C6 N1A C1 C2 -152.4(12) . . . . ? C13A N1A C1 C6 -152.6(11) . . . . ? C13A N1A C1 C13 2.3(8) . . . . ? C6 N1A C1 C13 155.0(6) . . . . ? O1 C13 C1 C2 28.6(4) . . . . ? N1 C13 C1 C2 -152.0(2) . . . . ? O1 C13 C1 C6 -147.1(3) . . . . ? N1 C13 C1 C6 32.3(3) . . . . ? O1 C13 C1 N1A -178.6(9) . . . . ? N1 C13 C1 N1A 0.8(8) . . . . ? data_dc5_32_m _database_code_depnum_ccdc_archive 'CCDC 285375' #=============================================================================== # 5. CHEMICAL DATA _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C13 H10 F N O' # Ex: 'C12 H16 N2 O6, H2 O' and '(Cd 2+)3, (C6 N6 Cr 3-)2, 2(H2 O)' _chemical_formula_structural ? _chemical_formula_sum 'C13 H10 F N O' _chemical_formula_iupac ? _chemical_formula_weight 215.22 _chemical_compound_source 'see text' loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source O O 0.0106 0.0060 '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' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' #=============================================================================== # 6. CRYSTAL DATA _symmetry_cell_setting Triclinic _symmetry_space_group_name_Hall '-P 1' _symmetry_space_group_name_H-M 'P -1' _symmetry_Int_Tables_number 2 loop_ _symmetry_equiv_pos_as_xyz x,y,z -x,-y,-z _cell_length_a 5.3691(10) _cell_length_b 7.8623(15) _cell_length_c 12.892(2) _cell_angle_alpha 72.465(3) _cell_angle_beta 80.495(3) _cell_angle_gamma 89.707(3) _cell_volume 511.24(16) _cell_formula_units_Z 2 _cell_measurement_temperature 290(2) _cell_measurement_reflns_used 780 _cell_measurement_theta_min 1.4 _cell_measurement_theta_max 25.8 _cell_special_details ; ? ; _exptl_crystal_description 'plates ' _exptl_crystal_colour colorless _exptl_crystal_size_max 0.20 _exptl_crystal_size_mid 0.18 _exptl_crystal_size_min 0.08 _exptl_crystal_size_rad ? _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.398 _exptl_crystal_density_method 'Not Measured' _exptl_crystal_F_000 224 _exptl_absorpt_coefficient_mu 0.101 _exptl_crystal_density_meas_temp ? # Permitted for _exptl_absorpt_correction_type : # analytical 'analytical from crystal shape' # Example: de Meulenaer&Tompa: ABST # cylinder 'cylindrical' # gaussian 'Gaussian from crystal shape' # Example: PLATON/ABSG # integration 'integration from crystal shape' # multi-scan 'symmetry-related measurements' # Example: SADABS, MULABS # none 'no absorption corr. applied' # numerical 'numerical from crystal shape' # psi-scan 'psi-scan corrections' # Example: PLATON/ABSP # refdelf 'refined from delta-F' # Example: SHELXA, DIFABS, DELABS # sphere 'spherical' # Example: PLATON/ABSS _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details '(SADABS; Sheldrick, 1996)' _exptl_absorpt_correction_T_min 0.9423 _exptl_absorpt_correction_T_max 0.9919 #=============================================================================== # 7. EXPERIMENTAL DATA _exptl_special_details ; ? ; _diffrn_ambient_temperature 290(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 'Bruker SMART APEX CCD area detector' _diffrn_measurement_method '\f and \w scans' _diffrn_detector_area_resol_mean ? # number of measured reflections (redundant set) _diffrn_reflns_number 3399 _diffrn_reflns_av_R_equivalents 0.0146 _diffrn_reflns_av_sigmaI/netI 0.0286 _diffrn_reflns_limit_h_min -6 _diffrn_reflns_limit_h_max 6 _diffrn_reflns_limit_k_min -8 _diffrn_reflns_limit_k_max 9 _diffrn_reflns_limit_l_min -15 _diffrn_reflns_limit_l_max 11 _diffrn_reflns_theta_min 2.72 _diffrn_reflns_theta_max 25.00 _diffrn_measured_fraction_theta_max 0.972 _diffrn_reflns_theta_full 25.00 _diffrn_measured_fraction_theta_full 0.972 _diffrn_reflns_reduction_process ; ? ; _reflns_number_total 1768 _reflns_number_gt 1619 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'SMART (Bruker, 1998)' _computing_cell_refinement SMART _computing_data_reduction 'SAINT (Bruker, 1998)' _computing_structure_solution 'SIR92 (Altomare et al., 1993)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Ortep-3 for Windows (Farrugia, 1997) and CAMERON (Watkin et al., 1993)' _computing_publication_material 'PLATON (Spek, 2003)' #=============================================================================== # 8. REFINEMENT DATA _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^)+(0.0295P)^2^+0.2526P] 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_number_reflns 1768 _refine_ls_number_parameters 185 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0711 _refine_ls_R_factor_gt 0.0626 _refine_ls_wR_factor_ref 0.1201 _refine_ls_wR_factor_gt 0.1165 _refine_ls_goodness_of_fit_ref 1.244 _refine_ls_restrained_S_all 1.244 _refine_ls_shift/su_max 0.000 _refine_ls_shift/su_mean 0.000 _refine_diff_density_max 0.186 _refine_diff_density_min -0.180 _refine_diff_density_rms 0.035 #=============================================================================== # 9. ATOMIC COORDINATES AND DISPLACEMENT PARAMETERS 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 0.1863(4) 0.2431(3) 0.53071(17) 0.0388(5) Uani 1 1 d . . . F1 F -0.0081(3) 0.2216(2) 0.96847(13) 0.0669(5) Uani 1 1 d . . . C12 C -0.0669(4) 0.3160(3) 0.6825(2) 0.0388(6) Uani 1 1 d . . . C9 C 0.2522(5) 0.1468(4) 0.8251(2) 0.0443(7) Uani 1 1 d . . . C8 C 0.3043(4) 0.1523(3) 0.7154(2) 0.0397(6) Uani 1 1 d . . . C6 C 0.2095(4) 0.1850(3) 0.3160(2) 0.0406(6) Uani 1 1 d . . . C7 C 0.1459(4) 0.2380(3) 0.64325(19) 0.0354(6) Uani 1 1 d . . . C11 C -0.1191(5) 0.3104(4) 0.7916(2) 0.0430(6) Uani 1 1 d . . . C10 C 0.0411(5) 0.2262(3) 0.8610(2) 0.0427(6) Uani 1 1 d . . . C2 C 0.6081(4) 0.3487(3) 0.2679(2) 0.0406(6) Uani 1 1 d . . . O1 O 0.6144(3) 0.2533(3) 0.49813(15) 0.0557(6) Uani 1 1 d . . . C3 C 0.6164(5) 0.3594(4) 0.1595(2) 0.0452(7) Uani 1 1 d . . . C1 C 0.4043(4) 0.2625(3) 0.34782(19) 0.0332(5) Uani 1 1 d . . . C5 C 0.2197(5) 0.1940(4) 0.2068(2) 0.0437(6) Uani 1 1 d . . . C13 C 0.4134(4) 0.2513(3) 0.4650(2) 0.0382(6) Uani 1 1 d . . . C4 C 0.4223(5) 0.2816(4) 0.1282(2) 0.0443(6) Uani 1 1 d . . . H4 H 0.441(4) 0.284(3) 0.049(2) 0.037(6) Uiso 1 1 d . . . H12 H -0.170(4) 0.375(3) 0.631(2) 0.040(7) Uiso 1 1 d . . . H9 H 0.356(5) 0.089(3) 0.877(2) 0.045(7) Uiso 1 1 d . . . H5 H 0.087(5) 0.145(4) 0.181(2) 0.058(8) Uiso 1 1 d . . . H11 H -0.260(5) 0.365(4) 0.821(2) 0.060(8) Uiso 1 1 d . . . H6 H 0.069(5) 0.122(3) 0.369(2) 0.045(7) Uiso 1 1 d . . . H3 H 0.756(5) 0.419(4) 0.102(2) 0.058(8) Uiso 1 1 d . . . H8 H 0.448(5) 0.099(3) 0.689(2) 0.045(7) Uiso 1 1 d . . . H2 H 0.739(5) 0.403(4) 0.292(2) 0.061(8) Uiso 1 1 d . . . H1N H 0.052(5) 0.256(3) 0.499(2) 0.044(7) 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 N1 0.0329(11) 0.0482(13) 0.0373(12) -0.0144(10) -0.0096(9) 0.0040(9) F1 0.0745(11) 0.0900(13) 0.0391(10) -0.0276(9) -0.0028(8) 0.0034(10) C12 0.0353(12) 0.0417(15) 0.0419(16) -0.0144(12) -0.0108(11) 0.0043(11) C9 0.0412(14) 0.0485(17) 0.0419(16) -0.0087(13) -0.0128(12) 0.0011(12) C8 0.0345(13) 0.0442(16) 0.0407(15) -0.0149(12) -0.0034(11) 0.0045(11) C6 0.0351(13) 0.0423(15) 0.0435(16) -0.0132(12) -0.0043(11) 0.0005(11) C7 0.0347(12) 0.0361(14) 0.0345(14) -0.0099(11) -0.0051(10) -0.0026(10) C11 0.0376(13) 0.0495(17) 0.0459(16) -0.0218(13) -0.0044(12) 0.0042(12) C10 0.0493(14) 0.0471(16) 0.0319(14) -0.0157(12) 0.0001(11) -0.0068(12) C2 0.0344(13) 0.0468(16) 0.0415(16) -0.0144(12) -0.0073(11) 0.0017(11) O1 0.0312(9) 0.0940(16) 0.0440(12) -0.0235(10) -0.0074(8) -0.0022(9) C3 0.0425(14) 0.0521(17) 0.0385(16) -0.0130(13) -0.0016(12) 0.0047(12) C1 0.0374(12) 0.0316(13) 0.0323(13) -0.0103(10) -0.0096(10) 0.0081(10) C5 0.0432(14) 0.0508(17) 0.0460(17) -0.0236(13) -0.0154(12) 0.0053(12) C13 0.0343(13) 0.0398(14) 0.0418(15) -0.0131(12) -0.0089(11) 0.0018(10) C4 0.0497(15) 0.0523(17) 0.0343(15) -0.0166(13) -0.0107(12) 0.0117(12) #=============================================================================== # 10. 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 C13 1.355(3) . ? N1 C7 1.419(3) . ? N1 H1N 0.88(3) . ? F1 C10 1.357(3) . ? C12 C11 1.375(4) . ? C12 C7 1.388(3) . ? C12 H12 0.94(2) . ? C9 C10 1.372(4) . ? C9 C8 1.384(4) . ? C9 H9 0.95(3) . ? C8 C7 1.386(3) . ? C8 H8 0.94(2) . ? C6 C5 1.380(4) . ? C6 C1 1.390(3) . ? C6 H6 0.95(3) . ? C11 C10 1.367(4) . ? C11 H11 0.95(3) . ? C2 C3 1.367(4) . ? C2 C1 1.390(3) . ? C2 H2 0.96(3) . ? O1 C13 1.226(3) . ? C3 C4 1.384(4) . ? C3 H3 0.97(3) . ? C1 C13 1.495(3) . ? C5 C4 1.381(4) . ? C5 H5 0.96(3) . ? C4 H4 1.01(2) . ? 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 C13 N1 C7 126.2(2) . . ? C13 N1 H1N 117.2(17) . . ? C7 N1 H1N 116.1(16) . . ? C11 C12 C7 120.5(2) . . ? C11 C12 H12 121.8(15) . . ? C7 C12 H12 117.7(15) . . ? C10 C9 C8 118.9(3) . . ? C10 C9 H9 118.7(15) . . ? C8 C9 H9 122.3(15) . . ? C9 C8 C7 120.1(2) . . ? C9 C8 H8 120.4(15) . . ? C7 C8 H8 119.4(15) . . ? C5 C6 C1 120.2(2) . . ? C5 C6 H6 118.5(15) . . ? C1 C6 H6 121.3(15) . . ? C8 C7 C12 119.4(2) . . ? C8 C7 N1 122.5(2) . . ? C12 C7 N1 118.1(2) . . ? C10 C11 C12 119.1(2) . . ? C10 C11 H11 118.1(17) . . ? C12 C11 H11 122.9(17) . . ? F1 C10 C11 119.3(2) . . ? F1 C10 C9 118.7(2) . . ? C11 C10 C9 122.0(2) . . ? C3 C2 C1 120.8(2) . . ? C3 C2 H2 122.3(17) . . ? C1 C2 H2 116.8(17) . . ? C2 C3 C4 120.1(3) . . ? C2 C3 H3 122.3(17) . . ? C4 C3 H3 117.6(16) . . ? C6 C1 C2 118.9(2) . . ? C6 C1 C13 123.5(2) . . ? C2 C1 C13 117.6(2) . . ? C6 C5 C4 120.2(3) . . ? C6 C5 H5 122.6(16) . . ? C4 C5 H5 117.2(16) . . ? O1 C13 N1 122.5(2) . . ? O1 C13 C1 121.8(2) . . ? N1 C13 C1 115.7(2) . . ? C5 C4 C3 119.7(3) . . ? C5 C4 H4 122.2(13) . . ? C3 C4 H4 118.0(13) . . ? 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 C10 C9 C8 C7 0.5(4) . . . . ? C9 C8 C7 C12 -0.9(4) . . . . ? C9 C8 C7 N1 -178.1(2) . . . . ? C11 C12 C7 C8 0.7(4) . . . . ? C11 C12 C7 N1 178.1(2) . . . . ? C13 N1 C7 C8 -34.3(4) . . . . ? C13 N1 C7 C12 148.4(2) . . . . ? C7 C12 C11 C10 -0.2(4) . . . . ? C12 C11 C10 F1 179.4(2) . . . . ? C12 C11 C10 C9 -0.1(4) . . . . ? C8 C9 C10 F1 -179.5(2) . . . . ? C8 C9 C10 C11 0.0(4) . . . . ? C1 C2 C3 C4 -1.0(4) . . . . ? C5 C6 C1 C2 0.0(4) . . . . ? C5 C6 C1 C13 -177.0(2) . . . . ? C3 C2 C1 C6 0.8(4) . . . . ? C3 C2 C1 C13 178.0(2) . . . . ? C1 C6 C5 C4 -0.7(4) . . . . ? C7 N1 C13 O1 0.8(4) . . . . ? C7 N1 C13 C1 -177.7(2) . . . . ? C6 C1 C13 O1 150.2(3) . . . . ? C2 C1 C13 O1 -26.9(4) . . . . ? C6 C1 C13 N1 -31.3(3) . . . . ? C2 C1 C13 N1 151.7(2) . . . . ? C6 C5 C4 C3 0.5(4) . . . . ? C2 C3 C4 C5 0.3(4) . . . . ? data_dc5_2a_m _database_code_depnum_ccdc_archive 'CCDC 285376' #=============================================================================== # 5. CHEMICAL DATA _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C13 H10 F N O' _chemical_formula_structural ? # Ex: 'C12 H16 N2 O6, H2 O' and '(Cd 2+)3, (C6 N6 Cr 3-)2, 2(H2 O)' _chemical_formula_sum 'C13 H10 F N O' _chemical_formula_weight 215.22 _chemical_compound_source ? loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source O O 0.0106 0.0060 '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' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' #=============================================================================== # 6. CRYSTAL DATA _symmetry_cell_setting Monoclinic _symmetry_space_group_name_Hall '-P 2ybc' _symmetry_space_group_name_H-M 'P 21/c' loop_ _symmetry_equiv_pos_as_xyz x,y,z -x,1/2+y,1/2-z -x,-y,-z x,1/2-y,1/2+z _cell_length_a 8.069(2) _cell_length_b 5.3914(14) _cell_length_c 23.238(6) _cell_angle_alpha 90 _cell_angle_beta 90.169(4) _cell_angle_gamma 90 _cell_volume 1011.0(4) _cell_formula_units_Z 4 _cell_measurement_temperature 290(2) _cell_measurement_reflns_used 965 _cell_measurement_theta_min 1.4 _cell_measurement_theta_max 25.8 _cell_special_details ; ? ; _exptl_crystal_description blocks _exptl_crystal_colour colorless _exptl_crystal_size_max 0.40 _exptl_crystal_size_mid 0.30 _exptl_crystal_size_min 0.20 _exptl_crystal_size_rad ? _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.414 _exptl_crystal_density_method 'Not Measured' _exptl_crystal_F_000 448 _exptl_absorpt_coefficient_mu 0.103 _exptl_crystal_density_meas_temp ? # Permitted for _exptl_absorpt_correction_type : # analytical 'analytical from crystal shape' # cylinder 'cylindrical' # empirical 'empirical from intensities' # gaussian 'Gaussian from crystal shape' # integration 'integration from crystal shape' # multi-scan 'symmetry-related measurements' # none 'no absorption corr. applied' # numerical 'numerical from crystal shape' # psi-scan 'psi-scan corrections' # refdelf 'refined from delta-F' # sphere 'spherical' _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details '(SADABS; Sheldrick, 1996)' _exptl_absorpt_correction_T_min 0.9308 _exptl_absorpt_correction_T_max 0.9798 #=============================================================================== # 7. EXPERIMENTAL DATA _exptl_special_details ; ? ; _diffrn_ambient_temperature 290(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 'Bruker SMART APEX CCD area detector' _diffrn_measurement_method '\f and \w scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? # number of measured reflections (redundant set) _diffrn_reflns_number 7141 _diffrn_reflns_av_R_equivalents 0.0209 _diffrn_reflns_av_sigmaI/netI 0.0226 _diffrn_reflns_limit_h_min -10 _diffrn_reflns_limit_h_max 9 _diffrn_reflns_limit_k_min -6 _diffrn_reflns_limit_k_max 6 _diffrn_reflns_limit_l_min -28 _diffrn_reflns_limit_l_max 28 _diffrn_reflns_theta_min 1.75 _diffrn_reflns_theta_max 27.30 _diffrn_measured_fraction_theta_max 0.922 _diffrn_reflns_theta_full 25.00 _diffrn_measured_fraction_theta_full 0.997 _diffrn_reflns_reduction_process ; ? ; _reflns_number_total 2045 _reflns_number_gt 1705 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'SMART (Bruker, 1998)' _computing_cell_refinement SMART _computing_data_reduction 'SAINT (Bruker, 1998)' _computing_structure_solution 'SIR92 (Altomare et al., 1993)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Ortep-3 for Windows (Farrugia, 1997) and CAMERON (Watkin et al., 1993)' _computing_publication_material 'PLATON (Spek, 2003)' #=============================================================================== # 8. REFINEMENT DATA _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^)+(0.0650P)^2^+0.3336P] 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_number_reflns 2045 _refine_ls_number_parameters 185 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0648 _refine_ls_R_factor_gt 0.0524 _refine_ls_wR_factor_ref 0.1287 _refine_ls_wR_factor_gt 0.1209 _refine_ls_goodness_of_fit_ref 1.022 _refine_ls_restrained_S_all 1.022 _refine_ls_shift/su_max 0.000 _refine_ls_shift/su_mean 0.000 _refine_diff_density_max 0.224 _refine_diff_density_min -0.180 _refine_diff_density_rms 0.045 #=============================================================================== # 9. ATOMIC COORDINATES AND DISPLACEMENT PARAMETERS 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 F1 F 0.28526(16) 0.4502(2) 0.29269(4) 0.0590(4) Uani 1 1 d . . . N1 N 0.2578(2) 0.7950(3) 0.48257(6) 0.0416(4) Uani 1 1 d . . . C8 C 0.2711(2) 0.6077(3) 0.38625(7) 0.0393(4) Uani 1 1 d . . . C6 C 0.0869(2) 0.8562(4) 0.59209(8) 0.0429(4) Uani 1 1 d . . . C7 C 0.3156(2) 0.7931(3) 0.42507(7) 0.0365(4) Uani 1 1 d . . . C12 C 0.4139(2) 0.9892(4) 0.40740(8) 0.0435(4) Uani 1 1 d . . . C9 C 0.3286(2) 0.6295(3) 0.33074(7) 0.0405(4) Uani 1 1 d . . . C1 C 0.1781(2) 0.6490(3) 0.57654(7) 0.0372(4) Uani 1 1 d . . . C2 C 0.2233(2) 0.4789(4) 0.61870(8) 0.0425(4) Uani 1 1 d . . . O1 O 0.24517(19) 0.3798(2) 0.49877(5) 0.0577(4) Uani 1 1 d . . . C10 C 0.4258(2) 0.8207(4) 0.31196(8) 0.0449(5) Uani 1 1 d . . . C4 C 0.0894(2) 0.7232(4) 0.69035(8) 0.0476(5) Uani 1 1 d . . . C13 C 0.2291(2) 0.5932(3) 0.51598(7) 0.0390(4) Uani 1 1 d . . . C5 C 0.0414(2) 0.8922(4) 0.64880(8) 0.0479(5) Uani 1 1 d . . . C3 C 0.1799(3) 0.5181(4) 0.67554(8) 0.0470(5) Uani 1 1 d . . . C11 C 0.4685(2) 1.0012(4) 0.35119(8) 0.0472(5) Uani 1 1 d . . . H3 H 0.215(2) 0.385(3) 0.7039(7) 0.031(4) Uiso 1 1 d . . . H11 H 0.534(2) 1.135(4) 0.3384(7) 0.034(4) Uiso 1 1 d . . . H8 H 0.198(3) 0.478(4) 0.3971(8) 0.048(5) Uiso 1 1 d . . . H2 H 0.288(2) 0.345(4) 0.6087(8) 0.046(5) Uiso 1 1 d . . . H6 H 0.056(3) 0.976(4) 0.5640(9) 0.050(5) Uiso 1 1 d . . . H12 H 0.442(2) 1.114(4) 0.4332(8) 0.047(5) Uiso 1 1 d . . . H4 H 0.058(3) 0.752(4) 0.7284(10) 0.056(6) Uiso 1 1 d . . . H10 H 0.465(2) 0.823(4) 0.2735(9) 0.048(5) Uiso 1 1 d . . . H5 H -0.026(3) 1.033(4) 0.6611(9) 0.060(6) Uiso 1 1 d . . . H1N H 0.258(2) 0.937(4) 0.4992(8) 0.053(6) 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 F1 0.0793(9) 0.0613(8) 0.0363(6) -0.0110(5) 0.0004(5) -0.0031(6) N1 0.0561(9) 0.0360(8) 0.0328(7) -0.0041(6) 0.0045(6) 0.0003(7) C8 0.0444(10) 0.0391(9) 0.0343(9) 0.0019(7) 0.0018(7) -0.0016(8) C6 0.0494(11) 0.0409(10) 0.0385(9) 0.0016(8) 0.0003(7) 0.0015(8) C7 0.0400(9) 0.0403(9) 0.0293(8) 0.0022(7) 0.0014(6) 0.0067(7) C12 0.0483(11) 0.0389(10) 0.0434(10) -0.0013(8) -0.0023(8) 0.0007(8) C9 0.0479(10) 0.0423(10) 0.0314(8) -0.0026(7) -0.0023(7) 0.0090(8) C1 0.0416(9) 0.0381(9) 0.0318(8) -0.0007(7) 0.0002(6) -0.0047(7) C2 0.0526(11) 0.0372(9) 0.0377(9) 0.0006(7) 0.0022(7) 0.0024(8) O1 0.1028(12) 0.0341(7) 0.0362(7) -0.0034(5) 0.0108(7) 0.0058(7) C10 0.0493(11) 0.0524(11) 0.0331(9) 0.0065(8) 0.0080(7) 0.0080(9) C4 0.0543(11) 0.0577(12) 0.0309(9) -0.0067(8) 0.0072(8) -0.0093(9) C13 0.0473(10) 0.0359(9) 0.0338(8) -0.0021(7) -0.0004(7) 0.0010(8) C5 0.0531(12) 0.0444(11) 0.0463(11) -0.0080(8) 0.0081(8) 0.0027(9) C3 0.0564(12) 0.0488(11) 0.0356(9) 0.0063(8) -0.0019(8) -0.0051(9) C11 0.0471(11) 0.0437(10) 0.0510(11) 0.0096(9) 0.0072(8) -0.0009(9) #=============================================================================== # 10. 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 F1 C9 1.355(2) . ? N1 C13 1.357(2) . ? N1 C7 1.416(2) . ? N1 H1N 0.86(2) . ? C8 C9 1.377(2) . ? C8 C7 1.393(2) . ? C8 H8 0.95(2) . ? C6 C5 1.383(3) . ? C6 C1 1.386(3) . ? C6 H6 0.95(2) . ? C7 C12 1.385(3) . ? C12 C11 1.381(3) . ? C12 H12 0.93(2) . ? C9 C10 1.368(3) . ? C1 C2 1.390(2) . ? C1 C13 1.498(2) . ? C2 C3 1.384(2) . ? C2 H2 0.92(2) . ? O1 C13 1.225(2) . ? C10 C11 1.376(3) . ? C10 H10 0.95(2) . ? C4 C3 1.369(3) . ? C4 C5 1.382(3) . ? C4 H4 0.93(2) . ? C5 H5 0.98(2) . ? C3 H3 1.013(17) . ? C11 H11 0.943(19) . ? 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 C13 N1 C7 126.24(15) . . ? C13 N1 H1N 117.2(13) . . ? C7 N1 H1N 115.5(13) . . ? C9 C8 C7 117.29(17) . . ? C9 C8 H8 121.5(12) . . ? C7 C8 H8 121.1(12) . . ? C5 C6 C1 120.27(17) . . ? C5 C6 H6 119.3(12) . . ? C1 C6 H6 120.4(12) . . ? C12 C7 C8 120.18(15) . . ? C12 C7 N1 117.68(16) . . ? C8 C7 N1 122.09(16) . . ? C7 C12 C11 120.04(18) . . ? C7 C12 H12 120.0(12) . . ? C11 C12 H12 120.0(12) . . ? F1 C9 C10 118.47(15) . . ? F1 C9 C8 117.60(16) . . ? C10 C9 C8 123.93(17) . . ? C6 C1 C2 119.10(16) . . ? C6 C1 C13 123.68(15) . . ? C2 C1 C13 117.21(16) . . ? C3 C2 C1 120.34(18) . . ? C3 C2 H2 120.3(12) . . ? C1 C2 H2 119.2(12) . . ? C9 C10 C11 117.66(16) . . ? C9 C10 H10 120.0(12) . . ? C11 C10 H10 122.3(12) . . ? C3 C4 C5 120.33(17) . . ? C3 C4 H4 121.3(13) . . ? C5 C4 H4 118.3(13) . . ? O1 C13 N1 123.22(16) . . ? O1 C13 C1 121.68(15) . . ? N1 C13 C1 115.10(15) . . ? C4 C5 C6 119.93(18) . . ? C4 C5 H5 117.6(12) . . ? C6 C5 H5 122.5(12) . . ? C4 C3 C2 120.02(18) . . ? C4 C3 H3 123.8(9) . . ? C2 C3 H3 116.1(9) . . ? C10 C11 C12 120.90(18) . . ? C10 C11 H11 118.1(10) . . ? C12 C11 H11 121.0(10) . . ? 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 C9 C8 C7 C12 0.0(3) . . . . ? C9 C8 C7 N1 177.31(15) . . . . ? C13 N1 C7 C12 -148.05(18) . . . . ? C13 N1 C7 C8 34.5(3) . . . . ? C8 C7 C12 C11 -0.2(3) . . . . ? N1 C7 C12 C11 -177.62(16) . . . . ? C7 C8 C9 F1 -179.79(15) . . . . ? C7 C8 C9 C10 0.0(3) . . . . ? C5 C6 C1 C2 -0.2(3) . . . . ? C5 C6 C1 C13 178.58(17) . . . . ? C6 C1 C2 C3 -1.0(3) . . . . ? C13 C1 C2 C3 -179.79(16) . . . . ? F1 C9 C10 C11 179.97(16) . . . . ? C8 C9 C10 C11 0.1(3) . . . . ? C7 N1 C13 O1 -2.7(3) . . . . ? C7 N1 C13 C1 176.43(15) . . . . ? C6 C1 C13 O1 -149.06(19) . . . . ? C2 C1 C13 O1 29.7(3) . . . . ? C6 C1 C13 N1 31.8(2) . . . . ? C2 C1 C13 N1 -149.45(17) . . . . ? C3 C4 C5 C6 -0.9(3) . . . . ? C1 C6 C5 C4 1.1(3) . . . . ? C5 C4 C3 C2 -0.2(3) . . . . ? C1 C2 C3 C4 1.2(3) . . . . ? C9 C10 C11 C12 -0.3(3) . . . . ? C7 C12 C11 C10 0.3(3) . . . . ? data_dc4_3_m _database_code_depnum_ccdc_archive 'CCDC 285377' #=============================================================================== # 5. CHEMICAL DATA _chemical_name_systematic ; ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C13 H10 F N O' # Ex: 'C12 H16 N2 O6, H2 O' and '(Cd 2+)3, (C6 N6 Cr 3-)2, 2(H2 O)' _chemical_formula_structural ? _chemical_formula_sum 'C13 H10 F N O' _chemical_formula_iupac ? _chemical_formula_weight 215.22 _chemical_compound_source ? loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source O O 0.0106 0.0060 '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' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' #=============================================================================== # 6. CRYSTAL DATA _symmetry_cell_setting Triclinic _symmetry_space_group_name_Hall '-P 1' _symmetry_space_group_name_H-M 'P -1' _symmetry_Int_Tables_number 2 loop_ _symmetry_equiv_pos_site_id _symmetry_equiv_pos_as_xyz 1 x,y,z 2 -x,-y,-z _cell_length_a 5.349(3) _cell_length_b 7.599(4) _cell_length_c 12.945(6) _cell_angle_alpha 92.124(8) _cell_angle_beta 101.179(7) _cell_angle_gamma 90.162(8) _cell_volume 515.8(5) _cell_formula_units_Z 2 _cell_measurement_temperature 290(2) _cell_measurement_reflns_used 775 _cell_measurement_theta_min 1.3 _cell_measurement_theta_max 25.4 _cell_special_details ; ; _exptl_crystal_description ' needle' _exptl_crystal_colour ' colorless' _exptl_crystal_size_max 0.25 _exptl_crystal_size_mid 0.19 _exptl_crystal_size_min 0.05 _exptl_crystal_size_rad ? _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.386 _exptl_crystal_density_method 'Not Measured' _exptl_crystal_F_000 224 _exptl_absorpt_coefficient_mu 0.101 _exptl_crystal_density_meas_temp ? # Permitted for _exptl_absorpt_correction_type : # analytical 'analytical from crystal shape' # Example: de Meulenaer&Tompa: ABST # cylinder 'cylindrical' # gaussian 'Gaussian from crystal shape' # Example: PLATON/ABSG # integration 'integration from crystal shape' # multi-scan 'symmetry-related measurements' # Example: SADABS, MULABS # none 'no absorption corr. applied' # numerical 'numerical from crystal shape' # psi-scan 'psi-scan corrections' # Example: PLATON/ABSP # refdelf 'refined from delta-F' # Example: SHELXA, DIFABS, DELABS # sphere 'spherical' # Example: PLATON/ABSS _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details '(SADABS; Sheldrick, 1996)' _exptl_absorpt_correction_T_min 0.9453 _exptl_absorpt_correction_T_max 0.9950 #=============================================================================== # 7. EXPERIMENTAL DATA _exptl_special_details ; ; _diffrn_ambient_temperature 290(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 'Bruker SMART APEX CCD area detector' _diffrn_measurement_method '\f and \w scans' _diffrn_detector_area_resol_mean ? # number of measured reflections (redundant set) _diffrn_reflns_number 3381 _diffrn_reflns_av_R_equivalents 0.0202 _diffrn_reflns_av_sigmaI/netI 0.0216 _diffrn_reflns_limit_h_min -5 _diffrn_reflns_limit_h_max 5 _diffrn_reflns_limit_k_min -7 _diffrn_reflns_limit_k_max 7 _diffrn_reflns_limit_l_min -12 _diffrn_reflns_limit_l_max 12 _diffrn_reflns_theta_min 1.60 _diffrn_reflns_theta_max 20.81 _diffrn_measured_fraction_theta_max 1.000 _diffrn_reflns_theta_full 20.81 _diffrn_measured_fraction_theta_full 1.000 _diffrn_reflns_reduction_process ; ; _reflns_number_total 1082 _reflns_number_gt 880 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'SMART (Bruker, 1998)' _computing_cell_refinement SMART _computing_data_reduction 'SAINT (Bruker, 1998)' _computing_structure_solution 'SIR92 (Altomare et al., 1993)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Ortep-3 for Windows (Farrugia, 1997) and CAMERON (Watkin et al., 1993)' _computing_publication_material 'PLATON (Spek, 2003)' #=============================================================================== # 8. REFINEMENT DATA _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^)+(0.0677P)^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 refall _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 1082 _refine_ls_number_parameters 185 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0469 _refine_ls_R_factor_gt 0.0323 _refine_ls_wR_factor_ref 0.1121 _refine_ls_wR_factor_gt 0.0821 _refine_ls_goodness_of_fit_ref 1.222 _refine_ls_restrained_S_all 1.222 _refine_ls_shift/su_max 0.000 _refine_ls_shift/su_mean 0.000 _refine_diff_density_max 0.158 _refine_diff_density_min -0.164 _refine_diff_density_rms 0.060 #=============================================================================== # 9. ATOMIC COORDINATES AND DISPLACEMENT PARAMETERS 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 F1 F 0.4206(3) 0.7737(3) 1.42280(13) 0.0679(7) Uani 1 1 d . . . N1 N 0.1687(5) 0.7429(3) 0.92229(18) 0.0374(7) Uani 1 1 d . . . O1 O 0.6007(3) 0.7564(3) 0.95873(13) 0.0539(7) Uani 1 1 d . . . C1 C 0.3904(5) 0.7591(3) 1.1039(2) 0.0321(7) Uani 1 1 d . . . C3 C 0.6005(6) 0.8522(4) 1.2796(2) 0.0428(8) Uani 1 1 d . . . C13 C 0.3970(5) 0.7525(3) 0.9896(2) 0.0362(7) Uani 1 1 d . . . C4 C 0.4104(6) 0.7694(4) 1.3169(2) 0.0411(8) Uani 1 1 d . . . C12 C -0.0940(5) 0.8108(4) 0.7554(2) 0.0389(8) Uani 1 1 d . . . C2 C 0.5895(5) 0.8435(4) 1.1727(2) 0.0382(8) Uani 1 1 d . . . C5 C 0.2109(6) 0.6827(4) 1.2535(2) 0.0416(8) Uani 1 1 d . . . C8 C 0.2878(5) 0.6499(4) 0.7546(2) 0.0401(8) Uani 1 1 d . . . C7 C 0.1242(5) 0.7346(3) 0.8103(2) 0.0332(7) Uani 1 1 d . . . C6 C 0.2013(5) 0.6789(4) 1.1464(2) 0.0380(8) Uani 1 1 d . . . C9 C 0.2331(6) 0.6436(4) 0.6462(2) 0.0447(8) Uani 1 1 d . . . C11 C -0.1479(6) 0.8029(4) 0.6475(2) 0.0447(8) Uani 1 1 d . . . C10 C 0.0151(6) 0.7188(4) 0.5919(2) 0.0466(8) Uani 1 1 d . . . H10 H -0.026(5) 0.716(3) 0.515(2) 0.044(8) Uiso 1 1 d . . . H9 H 0.345(5) 0.587(3) 0.606(2) 0.046(8) Uiso 1 1 d . . . H3 H 0.736(6) 0.917(4) 1.327(2) 0.062(9) Uiso 1 1 d . . . H12 H -0.206(5) 0.866(3) 0.7933(19) 0.044(8) Uiso 1 1 d . . . H5 H 0.090(5) 0.622(3) 1.285(2) 0.051(8) Uiso 1 1 d . . . H8 H 0.434(5) 0.596(3) 0.7910(19) 0.040(7) Uiso 1 1 d . . . H11 H -0.300(6) 0.857(4) 0.608(2) 0.058(9) Uiso 1 1 d . . . H2 H 0.708(5) 0.897(3) 1.1445(19) 0.038(8) Uiso 1 1 d . . . H6 H 0.072(5) 0.622(3) 1.1021(18) 0.029(7) Uiso 1 1 d . . . H1N H 0.044(6) 0.761(4) 0.950(2) 0.051(10) 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 F1 0.0705(13) 0.0952(15) 0.0380(12) 0.0033(9) 0.0108(9) -0.0019(10) N1 0.0284(14) 0.0502(16) 0.0341(16) 0.0009(11) 0.0073(13) 0.0024(11) O1 0.0319(12) 0.0875(17) 0.0430(13) 0.0017(11) 0.0093(10) -0.0048(10) C1 0.0296(16) 0.0311(16) 0.0361(18) 0.0030(13) 0.0072(14) 0.0019(13) C3 0.0395(18) 0.048(2) 0.038(2) -0.0033(15) 0.0010(15) 0.0016(15) C13 0.0297(17) 0.0371(18) 0.0417(19) 0.0033(13) 0.0061(16) 0.0003(12) C4 0.0476(19) 0.0490(19) 0.0273(19) 0.0052(14) 0.0083(16) 0.0091(16) C12 0.0306(17) 0.0456(19) 0.041(2) -0.0019(15) 0.0084(16) 0.0024(14) C2 0.0300(17) 0.0388(18) 0.046(2) 0.0048(15) 0.0081(16) -0.0018(14) C5 0.0382(18) 0.0478(19) 0.040(2) 0.0066(15) 0.0094(16) -0.0005(15) C8 0.0325(17) 0.0432(19) 0.044(2) 0.0014(15) 0.0059(15) 0.0026(14) C7 0.0303(16) 0.0358(16) 0.0328(19) 0.0005(13) 0.0048(13) -0.0036(13) C6 0.0315(17) 0.0395(18) 0.041(2) 0.0003(15) 0.0008(16) -0.0033(14) C9 0.046(2) 0.050(2) 0.041(2) -0.0069(15) 0.0162(17) -0.0020(16) C11 0.0371(18) 0.056(2) 0.039(2) 0.0033(15) 0.0021(16) 0.0035(15) C10 0.0474(19) 0.059(2) 0.032(2) 0.0011(15) 0.0041(17) -0.0047(16) #=============================================================================== # 10. 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 F1 C4 1.360(3) . ? N1 C13 1.356(3) . ? N1 C7 1.422(3) . ? N1 H1N 0.83(3) . ? O1 C13 1.231(3) . ? C1 C2 1.387(4) . ? C1 C6 1.390(4) . ? C1 C13 1.486(4) . ? C3 C4 1.368(4) . ? C3 C2 1.373(4) . ? C3 H3 0.98(3) . ? C4 C5 1.365(4) . ? C12 C11 1.369(4) . ? C12 C7 1.384(4) . ? C12 H12 0.93(3) . ? C2 H2 0.89(3) . ? C5 C6 1.377(4) . ? C5 H5 0.96(3) . ? C8 C9 1.376(4) . ? C8 C7 1.383(4) . ? C8 H8 0.93(3) . ? C6 H6 0.90(2) . ? C9 C10 1.377(4) . ? C9 H9 0.96(3) . ? C11 C10 1.378(4) . ? C11 H11 0.97(3) . ? C10 H10 0.98(3) . ? 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 C13 N1 C7 127.3(3) . . ? C13 N1 H1N 114.7(19) . . ? C7 N1 H1N 117.2(19) . . ? C2 C1 C6 118.0(3) . . ? C2 C1 C13 118.2(2) . . ? C6 C1 C13 123.7(2) . . ? C4 C3 C2 117.4(3) . . ? C4 C3 H3 120.9(16) . . ? C2 C3 H3 121.7(17) . . ? O1 C13 N1 122.4(3) . . ? O1 C13 C1 121.1(2) . . ? N1 C13 C1 116.5(2) . . ? F1 C4 C5 118.2(3) . . ? F1 C4 C3 118.3(3) . . ? C5 C4 C3 123.4(3) . . ? C11 C12 C7 120.7(3) . . ? C11 C12 H12 120.5(15) . . ? C7 C12 H12 118.8(15) . . ? C3 C2 C1 121.9(3) . . ? C3 C2 H2 120.8(16) . . ? C1 C2 H2 117.3(16) . . ? C4 C5 C6 118.0(3) . . ? C4 C5 H5 118.8(15) . . ? C6 C5 H5 123.1(16) . . ? C9 C8 C7 119.9(3) . . ? C9 C8 H8 120.5(15) . . ? C7 C8 H8 119.7(15) . . ? C8 C7 C12 119.1(3) . . ? C8 C7 N1 122.4(2) . . ? C12 C7 N1 118.5(3) . . ? C5 C6 C1 121.1(3) . . ? C5 C6 H6 120.3(15) . . ? C1 C6 H6 118.5(15) . . ? C8 C9 C10 120.9(3) . . ? C8 C9 H9 121.3(16) . . ? C10 C9 H9 117.8(16) . . ? C12 C11 C10 120.3(3) . . ? C12 C11 H11 121.4(16) . . ? C10 C11 H11 118.2(16) . . ? C9 C10 C11 119.2(3) . . ? C9 C10 H10 121.9(14) . . ? C11 C10 H10 118.9(14) . . ? 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 N1 C13 O1 0.5(4) . . . . ? C7 N1 C13 C1 -179.7(2) . . . . ? C2 C1 C13 O1 27.7(4) . . . . ? C6 C1 C13 O1 -149.5(3) . . . . ? C2 C1 C13 N1 -152.0(2) . . . . ? C6 C1 C13 N1 30.8(4) . . . . ? C2 C3 C4 F1 178.8(2) . . . . ? C2 C3 C4 C5 -1.2(4) . . . . ? C4 C3 C2 C1 1.9(4) . . . . ? C6 C1 C2 C3 -1.3(4) . . . . ? C13 C1 C2 C3 -178.6(2) . . . . ? F1 C4 C5 C6 179.9(2) . . . . ? C3 C4 C5 C6 0.0(4) . . . . ? C9 C8 C7 C12 0.5(4) . . . . ? C9 C8 C7 N1 179.0(2) . . . . ? C11 C12 C7 C8 0.0(4) . . . . ? C11 C12 C7 N1 -178.6(2) . . . . ? C13 N1 C7 C8 33.5(4) . . . . ? C13 N1 C7 C12 -148.0(3) . . . . ? C4 C5 C6 C1 0.7(4) . . . . ? C2 C1 C6 C5 -0.1(4) . . . . ? C13 C1 C6 C5 177.1(2) . . . . ? C7 C8 C9 C10 -0.9(4) . . . . ? C7 C12 C11 C10 -0.1(4) . . . . ? C8 C9 C10 C11 0.8(4) . . . . ? C12 C11 C10 C9 -0.3(4) . . . . ? #=============================================================================== data_dc4_1_m _database_code_depnum_ccdc_archive 'CCDC 285378' #=============================================================================== # 5. CHEMICAL DATA _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C13 H10 F N O' _chemical_formula_structural ? # Ex: 'C12 H16 N2 O6, H2 O' and '(Cd 2+)3, (C6 N6 Cr 3-)2, 2(H2 O)' _chemical_formula_sum 'C13 H10 F N O' _chemical_formula_weight 215.22 _chemical_compound_source ? loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source O O 0.0106 0.0060 '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' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' #=============================================================================== # 6. CRYSTAL DATA _symmetry_cell_setting Monoclinic _symmetry_space_group_name_Hall 'P 2yb' _symmetry_space_group_name_H-M 'P 21' loop_ _symmetry_equiv_pos_as_xyz x,y,z -x,1/2+y,-z _cell_length_a 5.4206(15) _cell_length_b 6.2580(17) _cell_length_c 15.534(4) _cell_angle_alpha 90 _cell_angle_beta 97.454(5) _cell_angle_gamma 90 _cell_volume 522.5(2) _cell_formula_units_Z 2 _cell_measurement_temperature 290(2) _cell_measurement_reflns_used 556 _cell_measurement_theta_min 1.6 _cell_measurement_theta_max 25.4 _cell_special_details ; ? ; _exptl_crystal_description plates _exptl_crystal_colour colorless _exptl_crystal_size_max 0.20 _exptl_crystal_size_mid 0.11 _exptl_crystal_size_min 0.07 _exptl_crystal_size_rad ? _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.368 _exptl_crystal_density_method 'Not Measured' _exptl_crystal_F_000 224 _exptl_absorpt_coefficient_mu 0.099 _exptl_crystal_density_meas_temp ? # Permitted for _exptl_absorpt_correction_type : # analytical 'analytical from crystal shape' # cylinder 'cylindrical' # empirical 'empirical from intensities' # gaussian 'Gaussian from crystal shape' # integration 'integration from crystal shape' # multi-scan 'symmetry-related measurements' # none 'no absorption corr. applied' # numerical 'numerical from crystal shape' # psi-scan 'psi-scan corrections' # refdelf 'refined from delta-F' # sphere 'spherical' _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details '(SADABS; Sheldrick, 1996)' _exptl_absorpt_correction_T_min 0.9434 _exptl_absorpt_correction_T_max 0.9931 #=============================================================================== # 7. EXPERIMENTAL DATA _exptl_special_details ; ? ; _diffrn_ambient_temperature 290(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 'Bruker SMART APEX CCD area detector' _diffrn_measurement_method '\f and \w scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? # number of measured reflections (redundant set) _diffrn_reflns_number 3606 _diffrn_reflns_av_R_equivalents 0.0336 _diffrn_reflns_av_sigmaI/netI 0.0736 _diffrn_reflns_limit_h_min -6 _diffrn_reflns_limit_h_max 6 _diffrn_reflns_limit_k_min -7 _diffrn_reflns_limit_k_max 7 _diffrn_reflns_limit_l_min -18 _diffrn_reflns_limit_l_max 18 _diffrn_reflns_theta_min 2.64 _diffrn_reflns_theta_max 24.99 _diffrn_measured_fraction_theta_max 1.000 _diffrn_reflns_theta_full 25.00 _diffrn_measured_fraction_theta_full 1.000 _diffrn_reflns_reduction_process ; ? ; _reflns_number_total 1783 _reflns_number_gt 1070 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'SMART (Bruker, 1998)' _computing_cell_refinement SMART _computing_data_reduction 'SAINT (Bruker, 1998)' _computing_structure_solution 'SIR92 (Altomare et al., 1993)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Ortep-3 for Windows (Farrugia, 1997) and CAMERON (Watkin et al., 1993)' _computing_publication_material 'PLATON (Spek, 2003)' #=============================================================================== # 8. REFINEMENT DATA _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^)+(0.0857P)^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 mixed _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 1783 _refine_ls_number_parameters 149 _refine_ls_number_restraints 1 _refine_ls_R_factor_all 0.1272 _refine_ls_R_factor_gt 0.0635 _refine_ls_wR_factor_ref 0.1116 _refine_ls_wR_factor_gt 0.0931 _refine_ls_goodness_of_fit_ref 1.001 _refine_ls_restrained_S_all 1.001 _refine_ls_shift/su_max 0.000 _refine_ls_shift/su_mean 0.000 _refine_diff_density_max 0.118 _refine_diff_density_min -0.108 _refine_diff_density_rms 0.031 #=============================================================================== # 9. ATOMIC COORDINATES AND DISPLACEMENT PARAMETERS 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 F1 F 0.0478(4) 0.2195(5) 0.38346(14) 0.0848(8) Uani 1 1 d . . . O1 O 0.6152(5) 0.2647(5) 0.23456(17) 0.0758(9) Uani 1 1 d . . . N1 N 0.2056(7) 0.3462(5) 0.2286(2) 0.0566(10) Uani 1 1 d . . . C6 C 0.2025(7) 0.0511(8) 0.3787(3) 0.0573(11) Uani 1 1 d . . . C12 C 0.0081(8) 0.6680(7) 0.1759(3) 0.0627(12) Uani 1 1 d . . . H12 H -0.1065 0.6434 0.2144 0.075 Uiso 1 1 calc R . . C1 C 0.3720(7) 0.0564(6) 0.3208(2) 0.0498(10) Uani 1 1 d . . . C7 C 0.1965(7) 0.5270(7) 0.1713(2) 0.0504(10) Uani 1 1 d . . . C5 C 0.1835(8) -0.1153(8) 0.4360(3) 0.0739(14) Uani 1 1 d . . . H5 H 0.0636 -0.1139 0.4737 0.089 Uiso 1 1 calc R . . C10 C 0.1541(8) 0.8842(8) 0.0662(3) 0.0719(14) Uani 1 1 d . . . H10 H 0.1408 1.0048 0.0310 0.086 Uiso 1 1 calc R . . C3 C 0.5195(8) -0.2841(8) 0.3797(3) 0.0718(12) Uani 1 1 d . . . H3 H 0.6277 -0.3995 0.3796 0.086 Uiso 1 1 calc R . . C13 C 0.4090(8) 0.2322(7) 0.2576(2) 0.0584(11) Uani 1 1 d . . . C11 C -0.0147(7) 0.8471(7) 0.1239(3) 0.0721(14) Uani 1 1 d . . . H11 H -0.1439 0.9431 0.1277 0.087 Uiso 1 1 calc R . . C4 C 0.3445(8) -0.2803(9) 0.4355(3) 0.0737(13) Uani 1 1 d . . . H4 H 0.3359 -0.3932 0.4739 0.088 Uiso 1 1 calc R . . C8 C 0.3625(7) 0.5622(8) 0.1134(3) 0.0667(12) Uani 1 1 d . . . H8 H 0.4900 0.4650 0.1090 0.080 Uiso 1 1 calc R . . C9 C 0.3405(8) 0.7398(9) 0.0621(3) 0.0789(13) Uani 1 1 d . . . H9 H 0.4552 0.7630 0.0234 0.095 Uiso 1 1 calc R . . C2 C 0.5345(8) -0.1152(7) 0.3233(3) 0.0656(12) Uani 1 1 d . . . H2 H 0.6562 -0.1166 0.2862 0.079 Uiso 1 1 calc R . . H1N H 0.060(8) 0.313(7) 0.250(3) 0.100(18) 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 F1 0.0825(16) 0.1021(19) 0.0759(15) 0.0070(16) 0.0335(13) 0.0184(19) O1 0.0501(16) 0.088(2) 0.094(2) 0.0186(19) 0.0252(15) 0.0039(19) N1 0.044(2) 0.063(3) 0.064(2) -0.003(2) 0.0127(19) -0.004(2) C6 0.055(3) 0.065(3) 0.051(3) -0.002(3) 0.005(2) 0.012(3) C12 0.060(3) 0.061(3) 0.070(3) 0.004(3) 0.017(2) 0.001(2) C1 0.060(3) 0.047(3) 0.044(2) -0.007(2) 0.013(2) -0.015(3) C7 0.053(3) 0.059(3) 0.041(2) 0.000(3) 0.012(2) -0.004(2) C5 0.067(3) 0.095(4) 0.059(3) 0.018(3) 0.003(2) -0.009(3) C10 0.069(3) 0.065(3) 0.081(4) 0.021(3) 0.006(3) -0.016(3) C3 0.078(3) 0.053(3) 0.084(3) 0.003(3) 0.007(3) -0.001(3) C13 0.047(2) 0.066(3) 0.062(3) -0.016(3) 0.006(2) 0.004(3) C11 0.053(3) 0.070(4) 0.092(3) -0.003(3) 0.003(3) 0.007(3) C4 0.066(3) 0.073(4) 0.078(3) 0.020(3) -0.007(3) -0.016(3) C8 0.067(3) 0.071(3) 0.063(3) 0.004(3) 0.013(2) 0.013(3) C9 0.062(3) 0.103(4) 0.075(3) 0.027(3) 0.019(2) -0.001(4) C2 0.067(3) 0.057(3) 0.075(3) -0.005(3) 0.020(2) 0.006(3) #=============================================================================== # 10. 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 F1 C6 1.355(5) . ? O1 C13 1.234(4) . ? N1 C13 1.341(5) . ? N1 C7 1.436(5) . ? N1 H1N 0.91(4) . ? C6 C1 1.367(5) . ? C6 C5 1.382(6) . ? C12 C7 1.358(5) . ? C12 C11 1.377(6) . ? C12 H12 0.9300 . ? C1 C2 1.386(5) . ? C1 C13 1.505(5) . ? C7 C8 1.371(5) . ? C5 C4 1.353(6) . ? C5 H5 0.9300 . ? C10 C9 1.363(6) . ? C10 C11 1.381(6) . ? C10 H10 0.9300 . ? C3 C4 1.366(5) . ? C3 C2 1.382(6) . ? C3 H3 0.9300 . ? C11 H11 0.9300 . ? C4 H4 0.9300 . ? C8 C9 1.364(6) . ? C8 H8 0.9300 . ? C9 H9 0.9300 . ? C2 H2 0.9300 . ? 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 C13 N1 C7 126.0(4) . . ? C13 N1 H1N 118(3) . . ? C7 N1 H1N 116(3) . . ? F1 C6 C1 119.4(4) . . ? F1 C6 C5 116.9(4) . . ? C1 C6 C5 123.7(4) . . ? C7 C12 C11 120.6(4) . . ? C7 C12 H12 119.7 . . ? C11 C12 H12 119.7 . . ? C6 C1 C2 116.2(4) . . ? C6 C1 C13 127.2(4) . . ? C2 C1 C13 116.5(4) . . ? C12 C7 C8 119.4(4) . . ? C12 C7 N1 116.5(4) . . ? C8 C7 N1 124.1(4) . . ? C4 C5 C6 118.0(4) . . ? C4 C5 H5 121.0 . . ? C6 C5 H5 121.0 . . ? C9 C10 C11 118.5(5) . . ? C9 C10 H10 120.8 . . ? C11 C10 H10 120.8 . . ? C4 C3 C2 119.4(5) . . ? C4 C3 H3 120.3 . . ? C2 C3 H3 120.3 . . ? O1 C13 N1 123.4(4) . . ? O1 C13 C1 120.8(4) . . ? N1 C13 C1 115.8(4) . . ? C12 C11 C10 120.0(4) . . ? C12 C11 H11 120.0 . . ? C10 C11 H11 120.0 . . ? C5 C4 C3 121.3(5) . . ? C5 C4 H4 119.4 . . ? C3 C4 H4 119.4 . . ? C9 C8 C7 120.0(4) . . ? C9 C8 H8 120.0 . . ? C7 C8 H8 120.0 . . ? C10 C9 C8 121.4(4) . . ? C10 C9 H9 119.3 . . ? C8 C9 H9 119.3 . . ? C3 C2 C1 121.4(4) . . ? C3 C2 H2 119.3 . . ? C1 C2 H2 119.3 . . ? 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 F1 C6 C1 C2 176.1(3) . . . . ? C5 C6 C1 C2 -1.7(6) . . . . ? F1 C6 C1 C13 -0.9(6) . . . . ? C5 C6 C1 C13 -178.7(4) . . . . ? C11 C12 C7 C8 -1.1(6) . . . . ? C11 C12 C7 N1 179.5(3) . . . . ? C13 N1 C7 C12 -155.1(4) . . . . ? C13 N1 C7 C8 25.6(5) . . . . ? F1 C6 C5 C4 -176.7(3) . . . . ? C1 C6 C5 C4 1.1(6) . . . . ? C7 N1 C13 O1 -3.6(6) . . . . ? C7 N1 C13 C1 177.0(3) . . . . ? C6 C1 C13 O1 150.7(4) . . . . ? C2 C1 C13 O1 -26.3(5) . . . . ? C6 C1 C13 N1 -29.9(5) . . . . ? C2 C1 C13 N1 153.2(3) . . . . ? C7 C12 C11 C10 0.3(6) . . . . ? C9 C10 C11 C12 0.3(6) . . . . ? C6 C5 C4 C3 -0.6(7) . . . . ? C2 C3 C4 C5 0.8(7) . . . . ? C12 C7 C8 C9 1.3(6) . . . . ? N1 C7 C8 C9 -179.4(4) . . . . ? C11 C10 C9 C8 -0.1(7) . . . . ? C7 C8 C9 C10 -0.7(7) . . . . ? C4 C3 C2 C1 -1.4(6) . . . . ? C6 C1 C2 C3 1.8(5) . . . . ? C13 C1 C2 C3 179.1(4) . . . . ? data_dc2_3 _database_code_depnum_ccdc_archive 'CCDC 285379' #=============================================================================== # 5. CHEMICAL DATA _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C13 H9 F2 N O' _chemical_formula_structural ? # Ex: 'C12 H16 N2 O6, H2 O' and '(Cd 2+)3, (C6 N6 Cr 3-)2, 2(H2 O)' _chemical_formula_sum 'C13 H9 F2 N O' _chemical_formula_weight 233.21 _chemical_compound_source ? loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source O O 0.0106 0.0060 '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' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' #=============================================================================== # 6. CRYSTAL DATA _symmetry_cell_setting Monoclinic _symmetry_space_group_name_Hall '-P 2ybc' _symmetry_space_group_name_H-M 'P 21/c' loop_ _symmetry_equiv_pos_as_xyz x,y,z -x,1/2+y,1/2-z -x,-y,-z x,1/2-y,1/2+z _cell_length_a 12.2353(16) _cell_length_b 10.8787(14) _cell_length_c 7.8648(10) _cell_angle_alpha 90 _cell_angle_beta 90.232(2) _cell_angle_gamma 90 _cell_volume 1046.8(2) _cell_formula_units_Z 4 _cell_measurement_temperature 290(2) _cell_measurement_reflns_used 555 _cell_measurement_theta_min 1.2 _cell_measurement_theta_max 25.4 _cell_special_details ; ? ; _exptl_crystal_description ' plates ' _exptl_crystal_colour colorless _exptl_crystal_size_max 0.45 _exptl_crystal_size_mid 0.43 _exptl_crystal_size_min 0.05 _exptl_crystal_size_rad ? _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.480 _exptl_crystal_density_method 'Not Measured' _exptl_crystal_F_000 480 _exptl_absorpt_coefficient_mu 0.119 _exptl_crystal_density_meas_temp ? # Permitted for _exptl_absorpt_correction_type : # analytical 'analytical from crystal shape' # cylinder 'cylindrical' # empirical 'empirical from intensities' # gaussian 'Gaussian from crystal shape' # integration 'integration from crystal shape' # multi-scan 'symmetry-related measurements' # none 'no absorption corr. applied' # numerical 'numerical from crystal shape' # psi-scan 'psi-scan corrections' # refdelf 'refined from delta-F' # sphere 'spherical' _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details '(SADABS; Sheldrick, 1996)' _exptl_absorpt_correction_T_min 0.9381 _exptl_absorpt_correction_T_max 0.9941 #=============================================================================== # 7. EXPERIMENTAL DATA _exptl_special_details ; ? ; _diffrn_ambient_temperature 290(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 'Bruker SMART APEX CCD area detector' _diffrn_measurement_method '\f and \w scans' # number of measured reflections (redundant set) _diffrn_reflns_number 7786 _diffrn_reflns_av_R_equivalents 0.0266 _diffrn_reflns_av_sigmaI/netI 0.0253 _diffrn_reflns_limit_h_min -15 _diffrn_reflns_limit_h_max 15 _diffrn_reflns_limit_k_min -12 _diffrn_reflns_limit_k_max 13 _diffrn_reflns_limit_l_min -9 _diffrn_reflns_limit_l_max 9 _diffrn_reflns_theta_min 1.66 _diffrn_reflns_theta_max 26.36 _diffrn_measured_fraction_theta_max 0.960 _diffrn_reflns_theta_full 25.00 _diffrn_measured_fraction_theta_full 0.977 _diffrn_reflns_reduction_process ; ? ; _reflns_number_total 2051 _reflns_number_gt 1670 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'SMART (Bruker, 1998)' _computing_cell_refinement SMART _computing_data_reduction 'SAINT (Bruker, 1998)' _computing_structure_solution 'SIR92 (Altomare et al., 1993)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Ortep-3 for Windows (Farrugia, 1997) and CAMERON (Watkin et al., 1993)' _computing_publication_material 'PLATON (Spek, 2003)' #=============================================================================== # 8. REFINEMENT DATA _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^)+(0.0369P)^2^+0.2256P] 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_number_reflns 2051 _refine_ls_number_parameters 190 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0685 _refine_ls_R_factor_gt 0.0499 _refine_ls_wR_factor_ref 0.1002 _refine_ls_wR_factor_gt 0.0933 _refine_ls_goodness_of_fit_ref 1.149 _refine_ls_restrained_S_all 1.149 _refine_ls_shift/su_max 0.000 _refine_ls_shift/su_mean 0.000 _refine_diff_density_max 0.185 _refine_diff_density_min -0.225 _refine_diff_density_rms 0.034 #=============================================================================== # 9. ATOMIC COORDINATES AND DISPLACEMENT PARAMETERS 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 F2 F 0.89773(8) 1.06031(11) 0.22360(17) 0.0623(4) Uani 1 1 d . . . N1 N 0.54829(12) 0.86011(16) 0.2261(2) 0.0375(4) Uani 1 1 d . . . F1 F 0.05271(9) 0.82266(13) 0.44500(18) 0.0686(4) Uani 1 1 d . . . O1 O 0.50136(10) 1.06169(12) 0.24338(19) 0.0531(4) Uani 1 1 d . . . C12 C 0.70257(15) 0.77422(18) 0.0820(2) 0.0387(4) Uani 1 1 d . . . C7 C 0.65912(13) 0.86951(16) 0.1757(2) 0.0332(4) Uani 1 1 d . . . C13 C 0.47692(13) 0.95327(17) 0.2567(2) 0.0351(4) Uani 1 1 d . . . C4 C 0.15578(15) 0.85305(18) 0.4000(3) 0.0437(5) Uani 1 1 d . . . C2 C 0.27763(14) 0.98829(17) 0.2634(3) 0.0374(4) Uani 1 1 d . . . C8 C 0.72471(15) 0.96796(18) 0.2242(3) 0.0388(5) Uani 1 1 d . . . C5 C 0.23969(16) 0.77595(19) 0.4473(3) 0.0447(5) Uani 1 1 d . . . C1 C 0.36478(13) 0.91309(16) 0.3077(2) 0.0324(4) Uani 1 1 d . . . C6 C 0.34471(15) 0.80633(17) 0.3990(2) 0.0390(5) Uani 1 1 d . . . C3 C 0.17192(15) 0.95854(19) 0.3094(3) 0.0435(5) Uani 1 1 d . . . C10 C 0.87837(15) 0.87149(18) 0.0845(3) 0.0426(5) Uani 1 1 d . . . C11 C 0.81142(16) 0.77512(19) 0.0373(3) 0.0440(5) Uani 1 1 d . . . C9 C 0.83282(14) 0.96506(17) 0.1761(3) 0.0400(5) Uani 1 1 d . . . H2 H 0.2894(13) 1.0611(17) 0.205(2) 0.031(5) Uiso 1 1 d . . . H8 H 0.6999(14) 1.0303(17) 0.286(2) 0.036(5) Uiso 1 1 d . . . H10 H 0.9521(16) 0.8751(17) 0.059(2) 0.042(5) Uiso 1 1 d . . . H6 H 0.4050(14) 0.7538(17) 0.432(2) 0.036(5) Uiso 1 1 d . . . H11 H 0.8410(16) 0.7112(18) -0.028(2) 0.046(5) Uiso 1 1 d . . . H12 H 0.6547(15) 0.7060(18) 0.049(2) 0.043(5) Uiso 1 1 d . . . H3 H 0.1115(16) 1.0102(18) 0.280(2) 0.045(5) Uiso 1 1 d . . . H5 H 0.2276(16) 0.704(2) 0.513(3) 0.053(6) Uiso 1 1 d . . . H1N H 0.5256(16) 0.789(2) 0.229(2) 0.043(6) 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 F2 0.0341(6) 0.0541(8) 0.0987(11) -0.0133(7) 0.0036(6) -0.0103(5) N1 0.0288(8) 0.0325(9) 0.0512(10) -0.0004(7) 0.0055(7) -0.0025(7) F1 0.0352(7) 0.0776(9) 0.0931(10) 0.0033(8) 0.0168(6) -0.0159(6) O1 0.0323(7) 0.0319(7) 0.0950(12) 0.0064(7) 0.0096(7) -0.0027(6) C12 0.0379(10) 0.0349(10) 0.0434(11) -0.0009(8) 0.0014(8) 0.0013(8) C7 0.0280(9) 0.0346(9) 0.0370(10) 0.0058(8) 0.0028(7) 0.0011(7) C13 0.0284(9) 0.0363(10) 0.0406(11) 0.0014(8) -0.0008(7) -0.0011(7) C4 0.0302(10) 0.0505(12) 0.0504(12) -0.0082(10) 0.0089(8) -0.0112(9) C2 0.0330(10) 0.0322(10) 0.0471(12) 0.0020(9) 0.0017(8) -0.0014(8) C8 0.0336(10) 0.0357(10) 0.0473(12) -0.0054(9) 0.0049(8) 0.0035(8) C5 0.0440(11) 0.0399(11) 0.0502(13) 0.0056(10) 0.0074(9) -0.0082(9) C1 0.0290(9) 0.0328(9) 0.0355(10) -0.0040(8) 0.0015(7) -0.0011(7) C6 0.0351(10) 0.0356(10) 0.0464(12) 0.0010(9) 0.0014(8) 0.0023(8) C3 0.0291(10) 0.0464(12) 0.0549(13) -0.0025(10) -0.0002(8) 0.0036(9) C10 0.0272(9) 0.0480(12) 0.0525(12) 0.0059(10) 0.0081(8) 0.0038(8) C11 0.0406(11) 0.0442(11) 0.0473(12) -0.0034(10) 0.0091(9) 0.0093(9) C9 0.0275(9) 0.0392(11) 0.0532(12) 0.0026(9) 0.0002(8) -0.0045(8) #=============================================================================== # 10. 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 F2 C9 1.357(2) . ? N1 C13 1.360(2) . ? N1 C7 1.418(2) . ? N1 H1N 0.83(2) . ? F1 C4 1.352(2) . ? O1 C13 1.221(2) . ? C12 C11 1.379(3) . ? C12 C7 1.380(2) . ? C12 H12 0.98(2) . ? C7 C8 1.391(2) . ? C13 C1 1.496(2) . ? C4 C3 1.365(3) . ? C4 C5 1.376(3) . ? C2 C3 1.383(3) . ? C2 C1 1.387(2) . ? C2 H2 0.926(18) . ? C8 C9 1.378(2) . ? C8 H8 0.891(19) . ? C5 C6 1.381(3) . ? C5 H5 0.95(2) . ? C1 C6 1.388(2) . ? C6 H6 0.968(18) . ? C3 H3 0.96(2) . ? C10 C9 1.367(3) . ? C10 C11 1.380(3) . ? C10 H10 0.926(19) . ? C11 H11 0.94(2) . ? 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 C13 N1 C7 127.68(17) . . ? C13 N1 H1N 118.8(14) . . ? C7 N1 H1N 113.4(14) . . ? C11 C12 C7 120.36(18) . . ? C11 C12 H12 121.0(11) . . ? C7 C12 H12 118.6(11) . . ? C12 C7 C8 120.13(16) . . ? C12 C7 N1 117.78(16) . . ? C8 C7 N1 122.02(16) . . ? O1 C13 N1 123.15(16) . . ? O1 C13 C1 122.02(16) . . ? N1 C13 C1 114.83(16) . . ? F1 C4 C3 118.62(18) . . ? F1 C4 C5 118.41(18) . . ? C3 C4 C5 122.97(17) . . ? C3 C2 C1 121.01(18) . . ? C3 C2 H2 118.5(10) . . ? C1 C2 H2 120.5(10) . . ? C9 C8 C7 117.43(17) . . ? C9 C8 H8 119.9(11) . . ? C7 C8 H8 122.7(11) . . ? C4 C5 C6 118.27(19) . . ? C4 C5 H5 122.1(13) . . ? C6 C5 H5 119.6(13) . . ? C2 C1 C6 119.07(16) . . ? C2 C1 C13 117.73(16) . . ? C6 C1 C13 123.19(16) . . ? C5 C6 C1 120.61(18) . . ? C5 C6 H6 119.6(11) . . ? C1 C6 H6 119.7(11) . . ? C4 C3 C2 118.07(18) . . ? C4 C3 H3 120.5(11) . . ? C2 C3 H3 121.4(11) . . ? C9 C10 C11 117.67(17) . . ? C9 C10 H10 118.9(12) . . ? C11 C10 H10 123.5(12) . . ? C12 C11 C10 120.65(18) . . ? C12 C11 H11 120.6(12) . . ? C10 C11 H11 118.7(12) . . ? F2 C9 C10 118.32(15) . . ? F2 C9 C8 117.92(17) . . ? C10 C9 C8 123.76(18) . . ? 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 C11 C12 C7 C8 0.7(3) . . . . ? C11 C12 C7 N1 -176.46(18) . . . . ? C13 N1 C7 C12 -152.11(18) . . . . ? C13 N1 C7 C8 30.8(3) . . . . ? C7 N1 C13 O1 0.1(3) . . . . ? C7 N1 C13 C1 179.80(17) . . . . ? C12 C7 C8 C9 -0.4(3) . . . . ? N1 C7 C8 C9 176.61(17) . . . . ? F1 C4 C5 C6 179.07(17) . . . . ? C3 C4 C5 C6 -0.8(3) . . . . ? C3 C2 C1 C6 0.2(3) . . . . ? C3 C2 C1 C13 -178.56(17) . . . . ? O1 C13 C1 C2 30.0(3) . . . . ? N1 C13 C1 C2 -149.63(17) . . . . ? O1 C13 C1 C6 -148.67(19) . . . . ? N1 C13 C1 C6 31.7(3) . . . . ? C4 C5 C6 C1 1.1(3) . . . . ? C2 C1 C6 C5 -0.8(3) . . . . ? C13 C1 C6 C5 177.86(18) . . . . ? F1 C4 C3 C2 -179.68(18) . . . . ? C5 C4 C3 C2 0.2(3) . . . . ? C1 C2 C3 C4 0.1(3) . . . . ? C7 C12 C11 C10 -0.4(3) . . . . ? C9 C10 C11 C12 -0.1(3) . . . . ? C11 C10 C9 F2 179.87(18) . . . . ? C11 C10 C9 C8 0.4(3) . . . . ? C7 C8 C9 F2 -179.61(17) . . . . ? C7 C8 C9 C10 -0.1(3) . . . . ? data_dc2_1am _database_code_depnum_ccdc_archive 'CCDC 285380' #=============================================================================== # 5. CHEMICAL DATA _chemical_name_systematic ; ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C13 H9 F2 N O' # Ex: 'C12 H16 N2 O6, H2 O' and '(Cd 2+)3, (C6 N6 Cr 3-)2, 2(H2 O)' _chemical_formula_structural ? _chemical_formula_sum 'C13 H9 F2 N O' _chemical_formula_iupac ? _chemical_formula_weight 233.21 _chemical_compound_source 'see text' loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source O O 0.0106 0.0060 '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' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' #=============================================================================== # 6. CRYSTAL DATA _symmetry_cell_setting Orthorhombic _symmetry_space_group_name_Hall 'P 2c -2ac' _symmetry_space_group_name_H-M 'P c a 21' _symmetry_Int_Tables_number 29 loop_ _symmetry_equiv_pos_site_id _symmetry_equiv_pos_as_xyz 1 x,y,z 2 -x,-y,1/2+z 3 1/2-x,y,1/2+z 4 1/2+x,-y,z _cell_length_a 24.660(5) _cell_length_b 5.2031(12) _cell_length_c 8.2440(18) _cell_angle_alpha 90 _cell_angle_beta 90 _cell_angle_gamma 90 _cell_volume 1057.8(4) _cell_formula_units_Z 4 _cell_measurement_temperature 290(2) _cell_measurement_reflns_used 685 _cell_measurement_theta_min 1.4 _cell_measurement_theta_max 25.4 _cell_special_details ; ; _exptl_crystal_description plates _exptl_crystal_colour colorless _exptl_crystal_size_max 0.50 _exptl_crystal_size_mid 0.38 _exptl_crystal_size_min 0.08 _exptl_crystal_size_rad ? _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.464 _exptl_crystal_density_method 'Not Measured' _exptl_crystal_F_000 480 _exptl_absorpt_coefficient_mu 0.117 _exptl_crystal_density_meas_temp ? # Permitted for _exptl_absorpt_correction_type : # analytical 'analytical from crystal shape' # Example: de Meulenaer&Tompa: ABST # cylinder 'cylindrical' # gaussian 'Gaussian from crystal shape' # Example: PLATON/ABSG # integration 'integration from crystal shape' # multi-scan 'symmetry-related measurements' # Example: SADABS, MULABS # none 'no absorption corr. applied' # numerical 'numerical from crystal shape' # psi-scan 'psi-scan corrections' # Example: PLATON/ABSP # refdelf 'refined from delta-F' # Example: SHELXA, DIFABS, DELABS # sphere 'spherical' # Example: PLATON/ABSS _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details '(SADABS; Sheldrick, 1996)' _exptl_absorpt_correction_T_min 0.9255 _exptl_absorpt_correction_T_max 0.9907 #=============================================================================== # 7. EXPERIMENTAL DATA _exptl_special_details ; ; _diffrn_ambient_temperature 290(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 'Bruker SMART APEX CCD area detector' _diffrn_measurement_method '\f and \w scans' # number of measured reflections (redundant set) _diffrn_reflns_number 6748 _diffrn_reflns_av_R_equivalents 0.0706 _diffrn_reflns_av_sigmaI/netI 0.0700 _diffrn_reflns_limit_h_min -29 _diffrn_reflns_limit_h_max 28 _diffrn_reflns_limit_k_min -6 _diffrn_reflns_limit_k_max 6 _diffrn_reflns_limit_l_min -9 _diffrn_reflns_limit_l_max 9 _diffrn_reflns_theta_min 1.65 _diffrn_reflns_theta_max 25.00 _diffrn_measured_fraction_theta_max 0.984 _diffrn_reflns_theta_full 25.00 _diffrn_measured_fraction_theta_full 0.984 _diffrn_reflns_reduction_process ; ; _reflns_number_total 1796 _reflns_number_gt 1291 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'SMART (Bruker, 1998)' _computing_cell_refinement SMART _computing_data_reduction 'SAINT (Bruker, 1998)' _computing_structure_solution 'SIR92 (Altomare et al., 1993)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Ortep-3 for Windows (Farrugia, 1997) and CAMERON (Watkin et al., 1993)' _computing_publication_material 'PLATON (Spek, 2003)' #=============================================================================== # 8. REFINEMENT DATA _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^)+(0.0397P)^2^+0.7164P] 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_number_reflns 1796 _refine_ls_number_parameters 155 _refine_ls_number_restraints 1 _refine_ls_R_factor_all 0.1259 _refine_ls_R_factor_gt 0.0853 _refine_ls_wR_factor_ref 0.1494 _refine_ls_wR_factor_gt 0.1356 _refine_ls_goodness_of_fit_ref 1.148 _refine_ls_restrained_S_all 1.148 _refine_ls_shift/su_max 0.001 _refine_ls_shift/su_mean 0.000 _refine_diff_density_max 0.238 _refine_diff_density_min -0.238 _refine_diff_density_rms 0.046 #=============================================================================== # 9. ATOMIC COORDINATES AND DISPLACEMENT PARAMETERS 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 F1 F -0.03373(14) -0.0139(7) 0.8954(5) 0.0654(11) Uani 1 1 d . . . O1 O 0.03761(13) 0.6150(6) 0.6899(6) 0.0589(12) Uani 1 1 d . . . F2 F 0.22522(13) 0.5366(8) 0.5750(6) 0.0891(14) Uani 1 1 d . . . N1 N 0.05370(15) 0.1926(7) 0.7342(6) 0.0373(10) Uani 1 1 d . . . C7 C 0.11101(19) 0.1972(9) 0.7357(8) 0.0389(12) Uani 1 1 d . . . C6 C -0.0643(2) 0.1539(10) 0.8071(7) 0.0395(13) Uani 1 1 d . . . C5 C -0.1197(2) 0.1256(11) 0.8195(8) 0.0539(17) Uani 1 1 d . . . H5 H -0.1348 -0.0041 0.8824 0.065 Uiso 1 1 calc R . . C12 C 0.1370(2) 0.0093(10) 0.8220(8) 0.0488(16) Uani 1 1 d . . . H12 H 0.1166 -0.1112 0.8786 0.059 Uiso 1 1 calc R . . C3 C -0.1283(2) 0.4879(10) 0.6441(7) 0.0484(16) Uani 1 1 d . . . H3 H -0.1500 0.6008 0.5856 0.058 Uiso 1 1 calc R . . C4 C -0.1522(2) 0.2975(10) 0.7347(9) 0.0495(14) Uani 1 1 d . . . H4 H -0.1897 0.2838 0.7394 0.059 Uiso 1 1 calc R . . C1 C -0.03992(19) 0.3444(8) 0.7208(7) 0.0384(12) Uani 1 1 d . . . C2 C -0.0738(2) 0.5140(10) 0.6385(7) 0.0439(15) Uani 1 1 d . . . H2 H -0.0587 0.6475 0.5786 0.053 Uiso 1 1 calc R . . C13 C 0.02036(19) 0.3980(9) 0.7169(7) 0.0395(12) Uani 1 1 d . . . C9 C 0.1955(2) 0.3586(12) 0.6563(9) 0.0592(19) Uani 1 1 d . . . C10 C 0.2230(2) 0.1782(12) 0.7430(10) 0.069(2) Uani 1 1 d . . . H10 H 0.2607 0.1782 0.7457 0.083 Uiso 1 1 calc R . . C11 C 0.1936(2) -0.0057(12) 0.8272(10) 0.070(2) Uani 1 1 d . . . H11 H 0.2110 -0.1350 0.8853 0.084 Uiso 1 1 calc R . . C8 C 0.1411(2) 0.3785(10) 0.6476(7) 0.0457(15) Uani 1 1 d . . . H8 H 0.1244 0.5059 0.5863 0.055 Uiso 1 1 calc R . . H1N H 0.0413 0.0149 0.7758 0.068(18) Uiso 1 1 d 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 F1 0.071(2) 0.057(2) 0.068(2) 0.0257(18) 0.0127(19) 0.0051(19) O1 0.040(2) 0.0284(19) 0.108(4) 0.017(2) 0.008(2) -0.0090(17) F2 0.062(2) 0.089(3) 0.117(4) 0.013(3) 0.013(2) -0.015(2) N1 0.039(2) 0.029(2) 0.044(3) -0.003(2) -0.005(2) 0.0017(19) C7 0.040(3) 0.030(3) 0.047(3) -0.010(3) -0.003(3) 0.006(2) C6 0.045(3) 0.031(3) 0.042(3) 0.003(3) 0.002(3) 0.009(3) C5 0.055(4) 0.037(3) 0.069(5) 0.007(4) 0.007(4) -0.012(3) C12 0.039(3) 0.034(3) 0.073(5) -0.005(3) -0.005(3) 0.002(3) C3 0.039(3) 0.047(4) 0.060(4) -0.003(3) -0.012(3) 0.012(3) C4 0.032(3) 0.048(3) 0.068(4) -0.010(4) 0.008(4) -0.006(3) C1 0.047(3) 0.025(3) 0.043(3) 0.001(3) 0.003(3) -0.009(2) C2 0.046(3) 0.044(3) 0.042(4) 0.012(3) 0.003(3) 0.008(3) C13 0.044(3) 0.035(3) 0.039(3) 0.008(3) 0.015(3) -0.010(2) C9 0.056(4) 0.047(4) 0.075(5) 0.011(4) 0.024(3) -0.005(3) C10 0.040(3) 0.067(4) 0.100(6) -0.010(5) 0.006(4) 0.004(3) C11 0.056(4) 0.055(4) 0.099(6) -0.017(4) 0.003(4) -0.001(3) C8 0.043(3) 0.037(3) 0.057(4) -0.004(3) -0.008(3) -0.002(3) #=============================================================================== # 10. 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 F1 C6 1.365(6) . ? O1 C13 1.227(5) . ? F2 C9 1.358(7) . ? N1 C13 1.356(6) . ? N1 C7 1.413(6) . ? N1 H1N 1.0326 . ? C7 C12 1.369(7) . ? C7 C8 1.404(7) . ? C6 C1 1.360(7) . ? C6 C5 1.377(7) . ? C5 C4 1.389(8) . ? C5 H5 0.9300 . ? C12 C11 1.398(8) . ? C12 H12 0.9300 . ? C3 C2 1.352(8) . ? C3 C4 1.373(7) . ? C3 H3 0.9300 . ? C4 H4 0.9300 . ? C1 C2 1.392(7) . ? C1 C13 1.513(6) . ? C2 H2 0.9300 . ? C9 C8 1.347(8) . ? C9 C10 1.360(8) . ? C10 C11 1.387(9) . ? C10 H10 0.9300 . ? C11 H11 0.9300 . ? C8 H8 0.9300 . ? 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 C13 N1 C7 126.4(4) . . ? C13 N1 H1N 124.1 . . ? C7 N1 H1N 108.0 . . ? C12 C7 C8 120.0(5) . . ? C12 C7 N1 117.5(5) . . ? C8 C7 N1 122.4(5) . . ? C1 C6 F1 120.0(5) . . ? C1 C6 C5 123.7(5) . . ? F1 C6 C5 116.1(5) . . ? C6 C5 C4 117.8(5) . . ? C6 C5 H5 121.1 . . ? C4 C5 H5 121.1 . . ? C7 C12 C11 121.6(6) . . ? C7 C12 H12 119.2 . . ? C11 C12 H12 119.2 . . ? C2 C3 C4 121.1(5) . . ? C2 C3 H3 119.4 . . ? C4 C3 H3 119.4 . . ? C3 C4 C5 119.4(5) . . ? C3 C4 H4 120.3 . . ? C5 C4 H4 120.3 . . ? C6 C1 C2 116.9(5) . . ? C6 C1 C13 125.5(5) . . ? C2 C1 C13 117.5(4) . . ? C3 C2 C1 121.1(5) . . ? C3 C2 H2 119.5 . . ? C1 C2 H2 119.5 . . ? O1 C13 N1 122.3(4) . . ? O1 C13 C1 120.9(4) . . ? N1 C13 C1 116.6(4) . . ? C8 C9 F2 117.2(6) . . ? C8 C9 C10 125.3(6) . . ? F2 C9 C10 117.5(6) . . ? C9 C10 C11 118.6(6) . . ? C9 C10 H10 120.7 . . ? C11 C10 H10 120.7 . . ? C10 C11 C12 117.9(7) . . ? C10 C11 H11 121.1 . . ? C12 C11 H11 121.1 . . ? C9 C8 C7 116.6(5) . . ? C9 C8 H8 121.7 . . ? C7 C8 H8 121.7 . . ? 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 C13 N1 C7 C12 151.6(6) . . . . ? C13 N1 C7 C8 -31.1(9) . . . . ? C1 C6 C5 C4 2.0(9) . . . . ? F1 C6 C5 C4 178.3(6) . . . . ? C8 C7 C12 C11 1.0(9) . . . . ? N1 C7 C12 C11 178.4(6) . . . . ? C2 C3 C4 C5 -1.3(9) . . . . ? C6 C5 C4 C3 -0.5(9) . . . . ? F1 C6 C1 C2 -177.7(5) . . . . ? C5 C6 C1 C2 -1.6(9) . . . . ? F1 C6 C1 C13 -2.3(8) . . . . ? C5 C6 C1 C13 173.8(6) . . . . ? C4 C3 C2 C1 1.8(9) . . . . ? C6 C1 C2 C3 -0.4(9) . . . . ? C13 C1 C2 C3 -176.1(5) . . . . ? C7 N1 C13 O1 4.7(9) . . . . ? C7 N1 C13 C1 -179.4(6) . . . . ? C6 C1 C13 O1 -152.7(6) . . . . ? C2 C1 C13 O1 22.7(9) . . . . ? C6 C1 C13 N1 31.4(8) . . . . ? C2 C1 C13 N1 -153.2(5) . . . . ? C8 C9 C10 C11 1.6(11) . . . . ? F2 C9 C10 C11 180.0(6) . . . . ? C9 C10 C11 C12 -1.8(10) . . . . ? C7 C12 C11 C10 0.6(10) . . . . ? F2 C9 C8 C7 -178.4(5) . . . . ? C10 C9 C8 C7 0.0(10) . . . . ? C12 C7 C8 C9 -1.3(8) . . . . ? N1 C7 C8 C9 -178.5(5) . . . . ? data_dc1_1_m _database_code_depnum_ccdc_archive 'CCDC 285381' #=============================================================================== # 5. CHEMICAL DATA _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_absolute_configuration unk _chemical_formula_moiety 'C13 H9 F2 N O' # Ex: 'C12 H16 N2 O6, H2 O' and '(Cd 2+)3, (C6 N6 Cr 3-)2, 2(H2 O)' _chemical_formula_structural ? _chemical_formula_sum 'C13 H9 F2 N O' _chemical_formula_iupac ? _chemical_formula_weight 233.21 _chemical_compound_source ? loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source O O 0.0106 0.0060 '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' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' #=============================================================================== # 6. CRYSTAL DATA _symmetry_cell_setting Orthorhombic _symmetry_space_group_name_Hall 'P 2ac 2ab' _symmetry_space_group_name_H-M 'P 21 21 21' _symmetry_Int_Tables_number 19 loop_ _symmetry_equiv_pos_as_xyz x,y,z 1/2-x,-y,1/2+z 1/2+x,1/2-y,-z -x,1/2+y,1/2-z _cell_length_a 5.1864(14) _cell_length_b 5.8673(16) _cell_length_c 35.127(9) _cell_angle_alpha 90 _cell_angle_beta 90 _cell_angle_gamma 90 _cell_volume 1068.9(5) _cell_formula_units_Z 4 _cell_measurement_temperature 290(2) _cell_measurement_reflns_used 565 _cell_measurement_theta_min 1.2 _cell_measurement_theta_max 25.2 _cell_special_details ; ? ; _exptl_crystal_description 'plates ' _exptl_crystal_colour ' colorless' _exptl_crystal_size_max 0.58 _exptl_crystal_size_mid 0.53 _exptl_crystal_size_min 0.13 _exptl_crystal_size_rad ? _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.449 _exptl_crystal_density_method 'Not Measured' _exptl_crystal_F_000 480 _exptl_absorpt_coefficient_mu 0.116 _exptl_crystal_density_meas_temp ? # Permitted for _exptl_absorpt_correction_type : # analytical 'analytical from crystal shape' # Example: de Meulenaer&Tompa: ABST # cylinder 'cylindrical' # gaussian 'Gaussian from crystal shape' # Example: PLATON/ABSG # integration 'integration from crystal shape' # multi-scan 'symmetry-related measurements' # Example: SADABS, MULABS # none 'no absorption corr. applied' # numerical 'numerical from crystal shape' # psi-scan 'psi-scan corrections' # Example: PLATON/ABSP # refdelf 'refined from delta-F' # Example: SHELXA, DIFABS, DELABS # sphere 'spherical' # Example: PLATON/ABSS _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details '(SADABS; Sheldrick, 1997)' _exptl_absorpt_correction_T_min 0.9056 _exptl_absorpt_correction_T_max 0.9851 #=============================================================================== # 7. EXPERIMENTAL DATA _exptl_special_details ; ? ; _diffrn_ambient_temperature 290(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 'Bruker SMART CCD area detector' _diffrn_measurement_method '\f and \w scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? # number of measured reflections (redundant set) _diffrn_reflns_number 7182 _diffrn_reflns_av_R_equivalents 0.0283 _diffrn_reflns_av_sigmaI/netI 0.0302 _diffrn_reflns_limit_h_min -6 _diffrn_reflns_limit_h_max 6 _diffrn_reflns_limit_k_min -7 _diffrn_reflns_limit_k_max 7 _diffrn_reflns_limit_l_min -42 _diffrn_reflns_limit_l_max 44 _diffrn_reflns_theta_min 1.16 _diffrn_reflns_theta_max 27.14 _diffrn_measured_fraction_theta_max 0.956 _diffrn_reflns_theta_full 25.00 _diffrn_measured_fraction_theta_full 1.000 _diffrn_reflns_reduction_process ; ? ; _reflns_number_total 1829 _reflns_number_gt 1551 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'SMART (Bruker, 1998)' _computing_cell_refinement SMART _computing_data_reduction 'SAINT (Bruker, 1998)' _computing_structure_solution 'SIR92 (Altomare et al., 1993)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Ortep-3 for Windows (Farrugia, 1997) and CAMERON (Watkin et al., 1993)' _computing_publication_material 'PLATON (Spek, 2003)' #=============================================================================== # 8. REFINEMENT DATA _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^)+(0.0000P)^2^+2.0915P] 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_number_reflns 1829 _refine_ls_number_parameters 158 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0890 _refine_ls_R_factor_gt 0.0760 _refine_ls_wR_factor_ref 0.1350 _refine_ls_wR_factor_gt 0.1310 _refine_ls_goodness_of_fit_ref 1.090 _refine_ls_restrained_S_all 1.090 _refine_ls_shift/su_max 0.000 _refine_ls_shift/su_mean 0.000 _refine_diff_density_max 0.354 _refine_diff_density_min -0.242 _refine_diff_density_rms 0.044 #=============================================================================== # 9. ATOMIC COORDINATES AND DISPLACEMENT PARAMETERS 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 F2 F 0.0184(8) -0.0586(7) 0.19142(10) 0.0926(13) Uani 1 1 d . . . F1 F 0.0537(8) 0.3493(7) 0.11935(11) 0.0925(13) Uani 1 1 d . . . O1 O 0.7136(7) -0.0850(7) 0.10701(12) 0.0763(13) Uani 1 1 d . . . C7 C 0.3742(13) -0.2365(9) 0.16280(15) 0.0598(17) Uani 1 1 d . . . C1 C 0.4032(12) 0.2062(9) 0.08382(15) 0.0547(14) Uani 1 1 d . . . C12 C 0.1972(13) -0.2307(10) 0.19144(18) 0.0642(15) Uani 1 1 d . . . C5 C 0.1715(12) 0.5454(10) 0.06452(17) 0.0656(16) Uani 1 1 d . . . H5 H 0.0421 0.6514 0.0693 0.079 Uiso 1 1 calc R . . C11 C 0.1908(11) -0.3848(10) 0.21956(17) 0.0648(16) Uani 1 1 d . . . H11 H 0.0691 -0.3735 0.2389 0.078 Uiso 1 1 calc R . . C2 C 0.5578(12) 0.2334(11) 0.05202(16) 0.0660(16) Uani 1 1 d . . . H2 H 0.6906 0.1300 0.0478 0.079 Uiso 1 1 calc R . . N1 N 0.3268(11) -0.0435(14) 0.1326(2) 0.106(3) Uani 1 1 d . . . C6 C 0.2102(12) 0.3660(10) 0.08834(15) 0.0586(14) Uani 1 1 d . . . C10 C 0.3670(11) -0.5602(11) 0.21941(19) 0.0711(17) Uani 1 1 d . . . H10 H 0.3616 -0.6718 0.2382 0.085 Uiso 1 1 calc R . . C3 C 0.5217(11) 0.4066(10) 0.02680(16) 0.0637(15) Uani 1 1 d . . . H3 H 0.6260 0.4180 0.0053 0.076 Uiso 1 1 calc R . . C8 C 0.5555(12) -0.4089(11) 0.16218(18) 0.0714(17) Uani 1 1 d . . . H8 H 0.6775 -0.4178 0.1428 0.086 Uiso 1 1 calc R . . C4 C 0.3294(12) 0.5659(10) 0.03317(17) 0.0657(16) Uani 1 1 d . . . H4 H 0.3069 0.6865 0.0163 0.079 Uiso 1 1 calc R . . C9 C 0.5499(11) -0.5693(11) 0.19146(18) 0.0685(16) Uani 1 1 d . . . H9 H 0.6729 -0.6845 0.1920 0.082 Uiso 1 1 calc R . . C13 C 0.4986(12) -0.0042(13) 0.1111(2) 0.091(3) Uani 1 1 d . . . H1N H 0.183(12) 0.002(10) 0.1367(16) 0.11(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 F2 0.109(3) 0.076(2) 0.093(3) -0.011(2) -0.017(2) 0.031(3) F1 0.092(3) 0.092(3) 0.094(3) -0.012(2) 0.022(2) -0.007(2) O1 0.042(2) 0.084(3) 0.103(3) 0.007(3) 0.017(2) 0.019(2) C7 0.098(5) 0.036(3) 0.046(3) -0.003(2) -0.027(3) -0.008(3) C1 0.072(4) 0.038(3) 0.054(3) -0.004(2) -0.016(3) 0.002(3) C12 0.065(4) 0.061(4) 0.067(4) -0.008(3) -0.013(3) 0.001(3) C5 0.059(3) 0.055(3) 0.083(4) -0.010(3) -0.011(3) 0.007(3) C11 0.058(3) 0.072(4) 0.064(3) 0.007(3) -0.007(3) -0.005(3) C2 0.065(4) 0.069(4) 0.064(3) -0.007(3) -0.005(3) 0.008(3) N1 0.046(3) 0.136(6) 0.134(6) -0.081(5) 0.018(4) 0.004(4) C6 0.067(3) 0.059(3) 0.049(3) -0.015(3) 0.007(3) -0.016(3) C10 0.056(3) 0.059(4) 0.098(5) 0.018(4) -0.010(3) -0.009(3) C3 0.061(3) 0.064(4) 0.067(4) 0.007(3) 0.009(3) 0.001(3) C8 0.066(4) 0.072(4) 0.076(4) -0.012(4) 0.005(3) -0.018(4) C4 0.073(4) 0.057(3) 0.067(4) 0.005(3) -0.013(3) -0.007(3) C9 0.051(3) 0.063(4) 0.091(4) 0.001(4) -0.012(3) 0.000(3) C13 0.047(3) 0.112(6) 0.114(6) -0.075(5) 0.008(4) -0.011(4) #=============================================================================== # 10. 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 F2 C12 1.371(7) . ? F1 C6 1.362(6) . ? O1 C13 1.221(7) . ? C7 C12 1.362(8) . ? C7 C8 1.381(8) . ? C7 N1 1.569(9) . ? C1 C6 1.381(8) . ? C1 C2 1.384(8) . ? C1 C13 1.640(9) . ? C12 C11 1.340(8) . ? C5 C6 1.359(8) . ? C5 C4 1.378(8) . ? C5 H5 0.9300 . ? C11 C10 1.376(8) . ? C11 H11 0.9300 . ? C2 C3 1.361(8) . ? C2 H2 0.9300 . ? N1 C13 1.191(9) . ? N1 H1N 0.80(6) . ? C10 C9 1.366(8) . ? C10 H10 0.9300 . ? C3 C4 1.385(8) . ? C3 H3 0.9300 . ? C8 C9 1.394(8) . ? C8 H8 0.9300 . ? C4 H4 0.9300 . ? C9 H9 0.9300 . ? 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 C12 C7 C8 119.2(6) . . ? C12 C7 N1 112.0(6) . . ? C8 C7 N1 128.6(6) . . ? C6 C1 C2 115.7(5) . . ? C6 C1 C13 131.5(5) . . ? C2 C1 C13 112.6(5) . . ? C11 C12 C7 123.0(6) . . ? C11 C12 F2 118.7(6) . . ? C7 C12 F2 118.3(6) . . ? C6 C5 C4 118.2(6) . . ? C6 C5 H5 120.9 . . ? C4 C5 H5 120.9 . . ? C12 C11 C10 119.1(6) . . ? C12 C11 H11 120.5 . . ? C10 C11 H11 120.5 . . ? C3 C2 C1 122.1(6) . . ? C3 C2 H2 118.9 . . ? C1 C2 H2 118.9 . . ? C13 N1 C7 116.8(7) . . ? C13 N1 H1N 138(5) . . ? C7 N1 H1N 106(4) . . ? C5 C6 F1 117.4(6) . . ? C5 C6 C1 124.2(5) . . ? F1 C6 C1 118.4(5) . . ? C9 C10 C11 119.5(6) . . ? C9 C10 H10 120.2 . . ? C11 C10 H10 120.2 . . ? C2 C3 C4 119.9(6) . . ? C2 C3 H3 120.1 . . ? C4 C3 H3 120.1 . . ? C7 C8 C9 117.9(6) . . ? C7 C8 H8 121.0 . . ? C9 C8 H8 121.0 . . ? C5 C4 C3 119.9(6) . . ? C5 C4 H4 120.1 . . ? C3 C4 H4 120.1 . . ? C10 C9 C8 121.2(6) . . ? C10 C9 H9 119.4 . . ? C8 C9 H9 119.4 . . ? N1 C13 O1 133.1(9) . . ? N1 C13 C1 106.9(7) . . ? O1 C13 C1 119.9(7) . . ? 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 C8 C7 C12 C11 0.5(9) . . . . ? N1 C7 C12 C11 176.8(5) . . . . ? C8 C7 C12 F2 -179.7(5) . . . . ? N1 C7 C12 F2 -3.4(7) . . . . ? C7 C12 C11 C10 -1.3(9) . . . . ? F2 C12 C11 C10 178.9(5) . . . . ? C6 C1 C2 C3 -0.1(8) . . . . ? C13 C1 C2 C3 -176.0(5) . . . . ? C12 C7 N1 C13 164.9(6) . . . . ? C8 C7 N1 C13 -19.2(9) . . . . ? C4 C5 C6 F1 179.5(5) . . . . ? C4 C5 C6 C1 2.1(9) . . . . ? C2 C1 C6 C5 -1.9(8) . . . . ? C13 C1 C6 C5 173.1(5) . . . . ? C2 C1 C6 F1 -179.3(5) . . . . ? C13 C1 C6 F1 -4.3(8) . . . . ? C12 C11 C10 C9 2.3(9) . . . . ? C1 C2 C3 C4 1.7(9) . . . . ? C12 C7 C8 C9 -0.6(8) . . . . ? N1 C7 C8 C9 -176.3(5) . . . . ? C6 C5 C4 C3 -0.3(9) . . . . ? C2 C3 C4 C5 -1.5(9) . . . . ? C11 C10 C9 C8 -2.5(9) . . . . ? C7 C8 C9 C10 1.7(9) . . . . ? C7 N1 C13 O1 0.3(11) . . . . ? C7 N1 C13 C1 -178.5(4) . . . . ? C6 C1 C13 N1 19.1(8) . . . . ? C2 C1 C13 N1 -165.7(6) . . . . ? C6 C1 C13 O1 -159.8(6) . . . . ? C2 C1 C13 O1 15.3(7) . . . . ? data_dc3_3 _database_code_depnum_ccdc_archive 'CCDC 644095' #=============================================================================== # 5. CHEMICAL DATA _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C13 H9 F2 N O' _chemical_formula_structural ? # Ex: 'C12 H16 N2 O6, H2 O' and '(Cd 2+)3, (C6 N6 Cr 3-)2, 2(H2 O)' _chemical_formula_sum 'C13 H9 F2 N O' _chemical_formula_weight 233.21 _chemical_compound_source ? loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source O O 0.0106 0.0060 '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' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' #=============================================================================== # 6. CRYSTAL DATA _symmetry_cell_setting Triclinic _symmetry_space_group_name_Hall '-P 1' _symmetry_space_group_name_H-M 'P -1' loop_ _symmetry_equiv_pos_as_xyz x,y,z -x,-y,-z _cell_length_a 5.460(2) _cell_length_b 7.693(3) _cell_length_c 13.038(5) _cell_angle_alpha 106.758(6) _cell_angle_beta 100.371(6) _cell_angle_gamma 90.016(6) _cell_volume 515.0(3) _cell_formula_units_Z 2 _cell_measurement_temperature 290(2) _cell_measurement_reflns_used 655 _cell_measurement_theta_min 1.4 _cell_measurement_theta_max 26.4 _cell_special_details ; ? ; _exptl_crystal_description prism _exptl_crystal_colour colorless _exptl_crystal_size_max 0.53 _exptl_crystal_size_mid 0.34 _exptl_crystal_size_min 0.09 _exptl_crystal_size_rad ? _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.504 _exptl_crystal_density_method 'Not Measured' _exptl_crystal_F_000 240 _exptl_absorpt_coefficient_mu 0.120 _exptl_crystal_density_meas_temp ? # Permitted for _exptl_absorpt_correction_type : # analytical 'analytical from crystal shape' # cylinder 'cylindrical' # empirical 'empirical from intensities' # gaussian 'Gaussian from crystal shape' # integration 'integration from crystal shape' # multi-scan 'symmetry-related measurements' # none 'no absorption corr. applied' # numerical 'numerical from crystal shape' # psi-scan 'psi-scan corrections' # refdelf 'refined from delta-F' # sphere 'spherical' _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details '(SADABS; Sheldrick, 1996)' _exptl_absorpt_correction_T_min 0.8903 _exptl_absorpt_correction_T_max 0.9892 #=============================================================================== # 7. EXPERIMENTAL DATA _exptl_special_details ; ? ; _diffrn_ambient_temperature 290(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 'Bruker SMART CCD area detector' _diffrn_measurement_method '\f and \w scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? # number of measured reflections (redundant set) _diffrn_reflns_number 3767 _diffrn_reflns_av_R_equivalents 0.0231 _diffrn_reflns_av_sigmaI/netI 0.0331 _diffrn_reflns_limit_h_min -6 _diffrn_reflns_limit_h_max 6 _diffrn_reflns_limit_k_min -9 _diffrn_reflns_limit_k_max 9 _diffrn_reflns_limit_l_min -15 _diffrn_reflns_limit_l_max 15 _diffrn_reflns_theta_min 1.66 _diffrn_reflns_theta_max 25.35 _diffrn_measured_fraction_theta_max 0.986 _diffrn_reflns_theta_full 25.00 _diffrn_measured_fraction_theta_full 0.986 _diffrn_reflns_reduction_process ; ? ; _reflns_number_total 1862 _reflns_number_gt 1431 _reflns_threshold_expression I>2\s(I) _computing_data_collection 'SMART (Bruker, 1998)' _computing_cell_refinement SMART _computing_data_reduction 'SAINT (Bruker, 1998)' _computing_structure_solution 'SIR92 (Altomare et al., 1993)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Ortep-3 for Windows (Farrugia, 1997) and CAMERON (Watkin et al., 1993)' _computing_publication_material 'PLATON (Spek, 2003)' #=============================================================================== # 8. REFINEMENT DATA _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^)+(0.0939P)^2^+0.2360P] 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_number_reflns 1862 _refine_ls_number_parameters 190 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0786 _refine_ls_R_factor_gt 0.0612 _refine_ls_wR_factor_ref 0.1729 _refine_ls_wR_factor_gt 0.1625 _refine_ls_goodness_of_fit_ref 1.059 _refine_ls_restrained_S_all 1.059 _refine_ls_shift/su_max 0.000 _refine_ls_shift/su_mean 0.000 _refine_diff_density_max 0.450 _refine_diff_density_min -0.238 _refine_diff_density_rms 0.060 #=============================================================================== # 9. ATOMIC COORDINATES AND DISPLACEMENT PARAMETERS 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 0.1886(4) 0.7452(3) 0.96604(19) 0.0413(6) Uani 1 1 d . . . F2 F -0.0270(3) 0.7179(3) 0.53203(13) 0.0614(6) Uani 1 1 d . . . F1 F 0.4421(3) 0.7800(3) 1.46567(13) 0.0619(6) Uani 1 1 d . . . C11 C -0.1283(5) 0.8064(4) 0.7066(2) 0.0410(7) Uani 1 1 d . . . C5 C 0.2241(5) 0.6886(4) 1.2854(2) 0.0420(7) Uani 1 1 d . . . C8 C 0.3031(5) 0.6574(4) 0.7831(2) 0.0386(6) Uani 1 1 d . . . C3 C 0.6241(5) 0.8539(4) 1.3326(2) 0.0410(7) Uani 1 1 d . . . C13 C 0.4144(5) 0.7532(4) 1.0308(2) 0.0402(6) Uani 1 1 d . . . C1 C 0.4073(5) 0.7606(3) 1.1461(2) 0.0354(6) Uani 1 1 d . . . C10 C 0.0300(5) 0.7250(4) 0.6382(2) 0.0385(6) Uani 1 1 d . . . C6 C 0.2124(5) 0.6829(4) 1.1779(2) 0.0401(6) Uani 1 1 d . . . C7 C 0.1452(5) 0.7397(3) 0.8544(2) 0.0348(6) Uani 1 1 d . . . O1 O 0.6121(3) 0.7552(3) 0.99884(15) 0.0525(6) Uani 1 1 d . . . C2 C 0.6107(5) 0.8444(4) 1.2253(2) 0.0387(6) Uani 1 1 d . . . C12 C -0.0684(5) 0.8142(4) 0.8146(2) 0.0382(6) Uani 1 1 d . . . C9 C 0.2438(5) 0.6499(4) 0.6747(2) 0.0409(7) Uani 1 1 d . . . C4 C 0.4286(5) 0.7742(4) 1.3608(2) 0.0380(6) Uani 1 1 d . . . H8 H 0.442(6) 0.605(4) 0.810(2) 0.045(8) Uiso 1 1 d . . . H9 H 0.335(6) 0.591(4) 0.625(2) 0.041(7) Uiso 1 1 d . . . H12 H -0.176(6) 0.877(4) 0.867(2) 0.045(7) Uiso 1 1 d . . . H11 H -0.278(6) 0.865(4) 0.680(2) 0.055(9) Uiso 1 1 d . . . H6 H 0.062(6) 0.621(4) 1.122(2) 0.054(8) Uiso 1 1 d . . . H1N H 0.067(7) 0.763(4) 1.008(2) 0.057(9) Uiso 1 1 d . . . H5 H 0.094(6) 0.635(4) 1.310(2) 0.050(8) Uiso 1 1 d . . . H3 H 0.754(7) 0.911(5) 1.391(3) 0.070(10) Uiso 1 1 d . . . H2 H 0.744(6) 0.909(4) 1.202(2) 0.061(9) 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 N1 0.0316(12) 0.0505(15) 0.0439(13) 0.0146(11) 0.0114(10) 0.0015(10) F2 0.0496(10) 0.0951(15) 0.0437(10) 0.0295(9) 0.0047(8) 0.0011(9) F1 0.0522(11) 0.0976(15) 0.0430(10) 0.0284(10) 0.0143(8) -0.0010(10) C11 0.0290(13) 0.0460(16) 0.0526(17) 0.0220(14) 0.0071(12) -0.0004(11) C5 0.0332(14) 0.0462(16) 0.0543(17) 0.0219(13) 0.0160(12) 0.0003(12) C8 0.0303(13) 0.0440(16) 0.0418(15) 0.0145(12) 0.0045(11) 0.0034(11) C3 0.0310(13) 0.0487(17) 0.0418(16) 0.0116(13) 0.0058(11) -0.0031(11) C13 0.0320(14) 0.0434(16) 0.0446(15) 0.0112(12) 0.0083(11) -0.0023(11) C1 0.0343(13) 0.0342(14) 0.0408(15) 0.0133(11) 0.0108(11) 0.0008(10) C10 0.0328(13) 0.0477(16) 0.0368(14) 0.0170(12) 0.0036(11) -0.0070(11) C6 0.0294(13) 0.0443(16) 0.0457(16) 0.0130(12) 0.0048(11) -0.0011(11) C7 0.0343(13) 0.0353(14) 0.0350(14) 0.0097(11) 0.0077(10) -0.0056(10) O1 0.0287(10) 0.0887(16) 0.0428(11) 0.0203(10) 0.0123(8) -0.0041(9) C2 0.0310(13) 0.0448(16) 0.0416(15) 0.0129(12) 0.0098(11) -0.0016(11) C12 0.0324(13) 0.0359(14) 0.0486(16) 0.0122(12) 0.0137(12) 0.0001(11) C9 0.0323(14) 0.0465(16) 0.0419(16) 0.0067(13) 0.0126(12) -0.0007(12) C4 0.0347(14) 0.0494(16) 0.0336(14) 0.0159(12) 0.0100(11) 0.0076(11) #=============================================================================== # 10. 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 C13 1.354(4) . ? N1 C7 1.421(3) . ? N1 H1N 0.92(3) . ? F2 C10 1.348(3) . ? F1 C4 1.344(3) . ? C11 C12 1.370(4) . ? C11 C10 1.375(4) . ? C11 H11 0.99(3) . ? C5 C4 1.370(4) . ? C5 C6 1.379(4) . ? C5 H5 0.97(3) . ? C8 C9 1.376(4) . ? C8 C7 1.399(4) . ? C8 H8 0.92(3) . ? C3 C2 1.368(4) . ? C3 C4 1.386(4) . ? C3 H3 0.95(4) . ? C13 O1 1.227(3) . ? C13 C1 1.495(4) . ? C1 C2 1.385(4) . ? C1 C6 1.402(4) . ? C10 C9 1.372(4) . ? C6 H6 1.00(3) . ? C7 C12 1.383(4) . ? C2 H2 1.02(3) . ? C12 H12 1.00(3) . ? C9 H9 0.90(3) . ? 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 C13 N1 C7 126.0(2) . . ? C13 N1 H1N 109.1(19) . . ? C7 N1 H1N 124.2(19) . . ? C12 C11 C10 118.8(2) . . ? C12 C11 H11 120.0(18) . . ? C10 C11 H11 121.0(18) . . ? C4 C5 C6 118.7(2) . . ? C4 C5 H5 118.5(17) . . ? C6 C5 H5 122.8(17) . . ? C9 C8 C7 120.0(3) . . ? C9 C8 H8 121.5(18) . . ? C7 C8 H8 118.5(18) . . ? C2 C3 C4 118.2(2) . . ? C2 C3 H3 127(2) . . ? C4 C3 H3 115(2) . . ? O1 C13 N1 123.3(3) . . ? O1 C13 C1 121.7(2) . . ? N1 C13 C1 115.1(2) . . ? C2 C1 C6 118.4(2) . . ? C2 C1 C13 117.5(2) . . ? C6 C1 C13 124.1(2) . . ? F2 C10 C9 119.0(2) . . ? F2 C10 C11 119.1(2) . . ? C9 C10 C11 121.9(2) . . ? C5 C6 C1 120.7(2) . . ? C5 C6 H6 118.9(17) . . ? C1 C6 H6 120.3(17) . . ? C12 C7 C8 119.2(2) . . ? C12 C7 N1 117.7(2) . . ? C8 C7 N1 123.1(2) . . ? C3 C2 C1 121.8(2) . . ? C3 C2 H2 120.5(18) . . ? C1 C2 H2 117.5(17) . . ? C11 C12 C7 120.9(2) . . ? C11 C12 H12 120.5(16) . . ? C7 C12 H12 118.5(16) . . ? C10 C9 C8 119.2(3) . . ? C10 C9 H9 118.0(17) . . ? C8 C9 H9 122.7(17) . . ? F1 C4 C5 119.1(2) . . ? F1 C4 C3 118.6(2) . . ? C5 C4 C3 122.3(2) . . ? 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 N1 C13 O1 -0.6(4) . . . . ? C7 N1 C13 C1 179.1(2) . . . . ? O1 C13 C1 C2 26.8(4) . . . . ? N1 C13 C1 C2 -152.9(3) . . . . ? O1 C13 C1 C6 -150.9(3) . . . . ? N1 C13 C1 C6 29.4(4) . . . . ? C12 C11 C10 F2 -179.6(2) . . . . ? C12 C11 C10 C9 0.8(4) . . . . ? C4 C5 C6 C1 1.0(4) . . . . ? C2 C1 C6 C5 -0.6(4) . . . . ? C13 C1 C6 C5 177.2(2) . . . . ? C9 C8 C7 C12 -0.6(4) . . . . ? C9 C8 C7 N1 177.1(2) . . . . ? C13 N1 C7 C12 -150.5(3) . . . . ? C13 N1 C7 C8 31.7(4) . . . . ? C4 C3 C2 C1 1.0(4) . . . . ? C6 C1 C2 C3 -0.5(4) . . . . ? C13 C1 C2 C3 -178.3(3) . . . . ? C10 C11 C12 C7 -0.9(4) . . . . ? C8 C7 C12 C11 0.8(4) . . . . ? N1 C7 C12 C11 -177.0(2) . . . . ? F2 C10 C9 C8 179.8(2) . . . . ? C11 C10 C9 C8 -0.6(4) . . . . ? C7 C8 C9 C10 0.5(4) . . . . ? C6 C5 C4 F1 -179.8(2) . . . . ? C6 C5 C4 C3 -0.5(4) . . . . ? C2 C3 C4 F1 178.8(2) . . . . ? C2 C3 C4 C5 -0.5(4) . . . . ? #===END