# Supplementary Material (ESI) for CrystEngComm # This journal is (c) The Royal Society of Chemistry 2011 data_global _journal_name_full CrystEngComm _journal_coden_Cambridge 1350 _publ_contact_author_name 'Gallagher, John' _publ_contact_author_email john.gallagher@dcu.ie _publ_section_title ; Structures and conformational analysis of a 3 x 3 isomer grid of nine N-(fluorophenyl)pyridinecarboxamides ; _publ_author_name J.Gallagher # C22 H22 C11 0.95 3.14 3.864(2) 133.8 3_566 no # C22 H22 C12 0.95 3.24 3.698(2) 111.3 3_566 no # C22 H22 C13 0.95 3.18 3.539(2) 104.3 3_566 no # C22 H22 C14 0.95 3.08 3.590(2) 115.1 3_566 no # C22 H22 C15 0.95 2.95 3.733(2) 140.8 3_566 no # C22 H22 C16 0.95 2.97 3.860(2) 155.9 3_566 no # C15 H15 C21 0.95 2.87 3.549(2) 129.7 2_556 no # C15 H15 C21 0.95 2.87 3.549(2) 129.7 2_556 no # C15 H15 N23 0.95 3.20 4.078(2) 153.8 2_556 no # C15 H15 C24 0.95 3.35 4.026(2) 130.3 2_556 no # C15 H15 C25 0.95 3.33 3.803(2) 113.0 2_556 no # C15 H15 C26 0.95 3.10 3.555(2) 111.5 2_556 no # Cg1 [C21,...,C26] and Cg2 [C11,...,C16] are the C~6~ aromatic ring # centroids located at sites 2_556 and 3_566, respectively. # Complete details for the C-H...\p(arene) interactions. #========================================================================= data_NmoF_[8-13] _database_code_depnum_ccdc_archive 'CCDC 722730' #TrackingRef '- NxxF-Final04.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common NmoF _chemical_melting_point 390 _chemical_formula_moiety 'C12 H9 F N2 O' _chemical_formula_sum 'C12 H9 F N2 O' _chemical_formula_weight 216.21 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' F F 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Orthorhombic _symmetry_space_group_name_H-M 'P 21 21 21' _symmetry_space_group_name_Hall 'P 2ac 2ab' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, -y, z+1/2' 'x+1/2, -y+1/2, -z' '-x, y+1/2, -z+1/2' _cell_length_a 4.0813(2) _cell_length_b 10.7319(7) _cell_length_c 22.5900(11) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 989.44(9) _cell_formula_units_Z 4 _cell_measurement_temperature 150(2) _cell_measurement_reflns_used 4723 _cell_measurement_theta_min 2.55 _cell_measurement_theta_max 27.5 _exptl_crystal_description block _exptl_crystal_colour colourless _exptl_crystal_size_max 0.12 _exptl_crystal_size_mid 0.08 _exptl_crystal_size_min 0.08 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.451 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 448 _exptl_absorpt_coefficient_mu 0.108 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.987 _exptl_absorpt_correction_T_max 0.991 _exptl_absorpt_process_details '(SORTAV; Blessing, 1995)' _exptl_special_details ; ? ; _diffrn_ambient_temperature 150(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed X-ray tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device 'Nonius KappaCCD' _diffrn_measurement_method '\f, \w scans with \k offsets' _diffrn_standards_number 4723 _diffrn_standards_decay_% ? _diffrn_reflns_number 4223 _diffrn_reflns_av_R_equivalents 0.0512 _diffrn_reflns_av_sigmaI/netI 0.0600 _diffrn_reflns_limit_h_min -4 _diffrn_reflns_limit_h_max 5 _diffrn_reflns_limit_k_min -10 _diffrn_reflns_limit_k_max 13 _diffrn_reflns_limit_l_min -28 _diffrn_reflns_limit_l_max 28 _diffrn_reflns_theta_min 2.62 _diffrn_reflns_theta_max 27.48 _diffrn_measured_fraction_theta_max 0.991 _diffrn_reflns_theta_full 27.48 _diffrn_measured_fraction_theta_full 0.991 _reflns_number_total 1364 _reflns_number_gt 957 _reflns_threshold_expression I>2\s(I) _computing_data_collection 'kappaCCD Server software (Nonius, 1997)' _computing_cell_refinement 'DENZO-SMN (Otwinowski and Minor, 1997)' _computing_data_reduction 'DENZO-SMN (Otwinowski and Minor, 1997)' _computing_structure_solution 'SHELXS97 (Sheldrick, 2008)' _computing_structure_refinement 'SHELXL97 (Sheldrick, 2008) and SORTX (McArdle, 1995)' _computing_molecular_graphics 'PLATON (Spek, 2009)' _computing_publication_material 'SHELXL97 and PREP8 (Ferguson, 1998)' _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 'w=1/[\s^2^(Fo^2^)+(0.0644P)^2^+0.144P] 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_abs_structure_details ? _refine_ls_abs_structure_Flack ? _refine_ls_number_reflns 1364 _refine_ls_number_parameters 149 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0848 _refine_ls_R_factor_gt 0.0486 _refine_ls_wR_factor_ref 0.1248 _refine_ls_wR_factor_gt 0.1074 _refine_ls_goodness_of_fit_ref 1.040 _refine_ls_restrained_S_all 1.040 _refine_ls_shift/su_max 0.000 _refine_ls_shift/su_mean 0.000 _refine_diff_density_max 0.253 _refine_diff_density_min -0.231 _refine_diff_density_rms 0.057 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 F12 F 0.1539(5) -0.29814(15) 0.18063(7) 0.0405(5) Uani 1 1 d . . . O1 O -0.0166(7) 0.10458(18) 0.11007(9) 0.0427(7) Uani 1 1 d . . . C1 C 0.0203(8) 0.0021(3) 0.08710(12) 0.0295(7) Uani 1 1 d . . . N1 N -0.0596(7) -0.1063(2) 0.11474(10) 0.0301(7) Uani 1 1 d . . . H1 H -0.033(9) -0.179(3) 0.0990(14) 0.042(10) Uiso 1 1 d . . . C11 C -0.1618(8) -0.1152(3) 0.17490(12) 0.0273(7) Uani 1 1 d . . . C12 C -0.0539(8) -0.2167(3) 0.20759(13) 0.0299(7) Uani 1 1 d . . . C13 C -0.1379(9) -0.2364(3) 0.26568(13) 0.0353(8) Uani 1 1 d . . . H13 H -0.0591 -0.3070 0.2867 0.042 Uiso 1 1 calc R . . C14 C -0.3404(9) -0.1504(3) 0.29272(13) 0.0369(8) Uani 1 1 d . . . H14 H -0.4061 -0.1624 0.3327 0.044 Uiso 1 1 calc R . . C15 C -0.4480(9) -0.0467(3) 0.26170(13) 0.0369(8) Uani 1 1 d . . . H15 H -0.5814 0.0134 0.2810 0.044 Uiso 1 1 calc R . . C16 C -0.3628(9) -0.0298(3) 0.20277(12) 0.0321(8) Uani 1 1 d . . . H16 H -0.4425 0.0405 0.1816 0.039 Uiso 1 1 calc R . . C21 C 0.1610(8) -0.0083(3) 0.02605(11) 0.0273(7) Uani 1 1 d . . . C22 C 0.2717(8) -0.1183(3) 0.00105(12) 0.0303(8) Uani 1 1 d . . . H22 H 0.2556 -0.1924 0.0239 0.036 Uiso 1 1 calc R . . N23 N 0.4018(8) -0.1266(2) -0.05408(10) 0.0344(7) Uani 1 1 d . . . C24 C 0.4256(10) -0.0205(3) -0.08469(13) 0.0346(8) Uani 1 1 d . . . H24 H 0.5142 -0.0241 -0.1235 0.041 Uiso 1 1 calc R . . C25 C 0.3289(10) 0.0944(3) -0.06314(12) 0.0340(8) Uani 1 1 d . . . H25 H 0.3545 0.1677 -0.0863 0.041 Uiso 1 1 calc R . . C26 C 0.1939(9) 0.1000(3) -0.00697(12) 0.0314(7) Uani 1 1 d . . . H26 H 0.1240 0.1776 0.0089 0.038 Uiso 1 1 calc R . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 F12 0.0540(12) 0.0291(10) 0.0384(9) -0.0005(8) -0.0019(10) 0.0056(10) O1 0.0702(18) 0.0231(10) 0.0347(12) -0.0012(10) 0.0089(12) -0.0002(13) C1 0.0375(19) 0.0212(13) 0.0299(15) 0.0006(13) -0.0029(14) -0.0023(16) N1 0.0427(17) 0.0201(12) 0.0276(13) -0.0007(11) -0.0006(13) -0.0010(13) C11 0.0318(17) 0.0236(14) 0.0264(13) -0.0018(13) -0.0034(14) -0.0072(16) C12 0.0335(19) 0.0243(14) 0.0321(16) -0.0027(14) -0.0043(15) -0.0038(16) C13 0.040(2) 0.0329(17) 0.0333(16) 0.0038(14) -0.0077(16) -0.0088(17) C14 0.0363(19) 0.0434(19) 0.0311(15) 0.0015(15) -0.0021(16) -0.0095(18) C15 0.0346(19) 0.0402(18) 0.0359(17) -0.0063(16) 0.0016(16) -0.0046(17) C16 0.0334(18) 0.0286(16) 0.0343(15) 0.0014(14) -0.0040(16) -0.0010(16) C21 0.0332(18) 0.0223(14) 0.0264(14) -0.0001(12) -0.0052(14) -0.0033(16) C22 0.0390(19) 0.0223(15) 0.0298(15) 0.0018(13) 0.0000(15) -0.0032(15) N23 0.0469(18) 0.0240(13) 0.0322(13) -0.0002(11) 0.0021(14) 0.0001(14) C24 0.045(2) 0.0300(16) 0.0288(15) 0.0016(13) 0.0006(15) -0.0001(17) C25 0.046(2) 0.0231(15) 0.0327(15) 0.0056(13) 0.0019(17) -0.0013(17) C26 0.0404(19) 0.0208(14) 0.0330(15) 0.0008(13) -0.0039(15) 0.0011(15) _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 F12 C12 1.361(4) . ? O1 C1 1.226(3) . ? C1 N1 1.360(3) . ? C1 C21 1.498(4) . ? N1 C11 1.425(3) . ? N1 H1 0.87(3) . ? C11 C16 1.382(4) . ? C11 C12 1.388(4) . ? C12 C13 1.373(4) . ? C13 C14 1.381(5) . ? C13 H13 0.9500 . ? C14 C15 1.387(4) . ? C14 H14 0.9500 . ? C15 C16 1.388(4) . ? C15 H15 0.9500 . ? C16 H16 0.9500 . ? C21 C22 1.384(4) . ? C21 C26 1.387(4) . ? C22 N23 1.357(3) . ? C22 H22 0.9500 . ? N23 C24 1.336(3) . ? C24 C25 1.383(4) . ? C24 H24 0.9500 . ? C25 C26 1.385(4) . ? C25 H25 0.9500 . ? C26 H26 0.9500 . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag O1 C1 N1 122.9(3) . . ? O1 C1 C21 120.2(3) . . ? N1 C1 C21 116.8(2) . . ? C1 N1 C11 124.5(2) . . ? C1 N1 H1 124(2) . . ? C11 N1 H1 112(2) . . ? C16 C11 C12 117.8(3) . . ? C16 C11 N1 124.3(3) . . ? C12 C11 N1 117.9(3) . . ? F12 C12 C13 119.0(3) . . ? F12 C12 C11 117.6(3) . . ? C13 C12 C11 123.4(3) . . ? C12 C13 C14 118.0(3) . . ? C12 C13 H13 121.0 . . ? C14 C13 H13 121.0 . . ? C13 C14 C15 120.2(3) . . ? C13 C14 H14 119.9 . . ? C15 C14 H14 119.9 . . ? C14 C15 C16 120.7(3) . . ? C14 C15 H15 119.7 . . ? C16 C15 H15 119.7 . . ? C11 C16 C15 119.9(3) . . ? C11 C16 H16 120.0 . . ? C15 C16 H16 120.0 . . ? C22 C21 C26 117.6(2) . . ? C22 C21 C1 124.3(2) . . ? C26 C21 C1 118.0(3) . . ? N23 C22 C21 123.9(3) . . ? N23 C22 H22 118.0 . . ? C21 C22 H22 118.0 . . ? C24 N23 C22 116.6(2) . . ? N23 C24 C25 123.8(3) . . ? N23 C24 H24 118.1 . . ? C25 C24 H24 118.1 . . ? C24 C25 C26 118.3(3) . . ? C24 C25 H25 120.8 . . ? C26 C25 H25 120.8 . . ? C25 C26 C21 119.7(3) . . ? C25 C26 H26 120.2 . . ? C21 C26 H26 120.2 . . ? 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 C1 N1 C11 -6.8(5) . . . . ? C21 C1 N1 C11 172.8(3) . . . . ? C1 N1 C11 C16 38.3(5) . . . . ? C1 N1 C11 C12 -142.1(3) . . . . ? C16 C11 C12 F12 -177.6(3) . . . . ? N1 C11 C12 F12 2.8(4) . . . . ? C16 C11 C12 C13 0.3(5) . . . . ? N1 C11 C12 C13 -179.3(3) . . . . ? F12 C12 C13 C14 177.9(3) . . . . ? C11 C12 C13 C14 0.0(5) . . . . ? C12 C13 C14 C15 -1.2(5) . . . . ? C13 C14 C15 C16 2.0(5) . . . . ? C12 C11 C16 C15 0.5(5) . . . . ? N1 C11 C16 C15 -179.9(3) . . . . ? C14 C15 C16 C11 -1.7(5) . . . . ? O1 C1 C21 C22 166.7(3) . . . . ? N1 C1 C21 C22 -12.9(5) . . . . ? O1 C1 C21 C26 -10.9(5) . . . . ? N1 C1 C21 C26 169.5(3) . . . . ? C26 C21 C22 N23 -1.7(5) . . . . ? C1 C21 C22 N23 -179.3(3) . . . . ? C21 C22 N23 C24 1.0(5) . . . . ? C22 N23 C24 C25 0.5(5) . . . . ? N23 C24 C25 C26 -1.2(6) . . . . ? C24 C25 C26 C21 0.4(5) . . . . ? C22 C21 C26 C25 1.0(5) . . . . ? C1 C21 C26 C25 178.7(3) . . . . ? loop_ _geom_hbond_atom_site_label_D _geom_hbond_atom_site_label_H _geom_hbond_atom_site_label_A _geom_hbond_distance_DH _geom_hbond_distance_HA _geom_hbond_distance_DA _geom_hbond_angle_DHA _geom_hbond_site_symmetry_A _geom_hbond_publ_flag # # Hydrogen bonding scheme # ======== ======= ====== # # D H A D-H H...A D...A D-H...A symm publ # - - - --- ----- ----- ------- ---- ---- N1 H1 N23 0.87(3) 2.33(3) 3.182(4) 166(4) 3_445 yes N1 H1 F12 0.87(3) 2.37(3) 2.686(3) 102(2) . yes C16 H16 O1 0.95 2.47 2.909(4) 108 . yes C13 H13 O1 0.95 2.54 3.345(4) 143 4_545 yes C22 H22 N23 0.95 2.52 3.348(4) 147 3_445 yes C24 H24 F12 0.95 2.37 3.059(4) 129 3_545 yes C25 H25 O1 0.95 2.56 3.458(4) 158 3 yes #===================================================================== data_NooF_[8-14] _database_code_depnum_ccdc_archive 'CCDC 722731' #TrackingRef '- NxxF-Final04.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common NooF _chemical_melting_point 379 _chemical_formula_moiety 'C12 H8.97 Cl0.03 F N2 O' _chemical_formula_sum 'C12 H8.97 Cl0.03 F N2 O' _chemical_formula_weight 217.33 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' F F 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Monoclinic _symmetry_space_group_name_H-M 'P 21/n' _symmetry_space_group_name_Hall '-P 2yn' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, y+1/2, -z+1/2' '-x, -y, -z' 'x-1/2, -y-1/2, z-1/2' _cell_length_a 4.8030(4) _cell_length_b 19.1318(18) _cell_length_c 10.8759(8) _cell_angle_alpha 90.00 _cell_angle_beta 99.276(5) _cell_angle_gamma 90.00 _cell_volume 986.32(14) _cell_formula_units_Z 4 _cell_measurement_temperature 150(2) _cell_measurement_reflns_used 12678 _cell_measurement_theta_min 2.55 _cell_measurement_theta_max 27.5 _exptl_crystal_description plate _exptl_crystal_colour colourless _exptl_crystal_size_max 0.20 _exptl_crystal_size_mid 0.15 _exptl_crystal_size_min 0.03 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.464 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 449.6 _exptl_absorpt_coefficient_mu 0.117 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.979 _exptl_absorpt_correction_T_max 0.997 _exptl_absorpt_process_details '(SORTAV; Blessing, 1995)' _exptl_special_details ; ? ; _diffrn_ambient_temperature 150(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type 'Molybdenum K\a' _diffrn_radiation_source 'fine-focus sealed X-ray tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device 'Nonius KappaCCD' _diffrn_measurement_method '\f, \w scans with \k offsets' _diffrn_standards_number 6843 _diffrn_standards_decay_% ? _diffrn_reflns_number 6707 _diffrn_reflns_av_R_equivalents 0.0765 _diffrn_reflns_av_sigmaI/netI 0.0897 _diffrn_reflns_limit_h_min -6 _diffrn_reflns_limit_h_max 6 _diffrn_reflns_limit_k_min -21 _diffrn_reflns_limit_k_max 24 _diffrn_reflns_limit_l_min -13 _diffrn_reflns_limit_l_max 13 _diffrn_reflns_theta_min 2.85 _diffrn_reflns_theta_max 27.5 _diffrn_measured_fraction_theta_max 0.987 _diffrn_reflns_theta_full 27.50 _diffrn_measured_fraction_theta_full 0.987 _reflns_number_total 2238 _reflns_number_gt 1160 _reflns_threshold_expression I>2\s(I) _computing_data_collection 'kappaCCD Server software (Nonius, 1997)' _computing_cell_refinement 'DENZO-SMN (Otwinowski and Minor, 1997)' _computing_data_reduction 'DENZO-SMN (Otwinowski and Minor, 1997)' _computing_structure_solution 'SHELXS97 (Sheldrick, 2008)' _computing_structure_refinement 'SHELXL97 (Sheldrick, 2008) and SORTX (McArdle, 1995)' _computing_molecular_graphics 'PLATON (Spek, 2003)' _computing_publication_material 'SHELXL97 and PREP8 (Ferguson, 1998)' _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 'w=1/[\s^2^(Fo^2^)+(0.0713P)^2^] 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 2238 _refine_ls_number_parameters 154 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.1325 _refine_ls_R_factor_gt 0.0568 _refine_ls_wR_factor_ref 0.1535 _refine_ls_wR_factor_gt 0.1227 _refine_ls_goodness_of_fit_ref 0.995 _refine_ls_restrained_S_all 0.995 _refine_ls_shift/su_max 0.000 _refine_ls_shift/su_mean 0.000 _refine_diff_density_max 0.220 _refine_diff_density_min -0.210 _refine_diff_density_rms 0.054 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 F12 F -0.0260(3) 0.16417(7) -0.06780(11) 0.0503(4) Uani 1 1 d . . . O1 O -0.1037(4) 0.08145(8) 0.35051(13) 0.0507(5) Uani 1 1 d . . . C1 C -0.0008(5) 0.06727(12) 0.2579(2) 0.0391(6) Uani 1 1 d . . . N1 N -0.0569(4) 0.10146(10) 0.14724(17) 0.0417(5) Uani 1 1 d . . . H1 H 0.046(5) 0.0834(12) 0.090(2) 0.050(7) Uiso 1 1 d . . . C11 C -0.2233(5) 0.16107(11) 0.1164(2) 0.0386(6) Uani 1 1 d . . . C12 C -0.2052(5) 0.19352(13) 0.0037(2) 0.0413(6) Uani 1 1 d . . . C13 C -0.3520(5) 0.25245(13) -0.0371(2) 0.0455(6) Uani 1 1 d . . . H13 H -0.3323 0.2730 -0.1148 0.055 Uiso 1 1 calc R . . C14 C -0.5299(5) 0.28156(13) 0.0371(2) 0.0449(6) Uani 1 1 d . . . H14 H -0.6342 0.3226 0.0107 0.054 Uiso 1 1 calc R . . C15 C -0.5554(5) 0.25074(12) 0.14967(19) 0.0438(6) Uani 1 1 d . . . H15 H -0.6781 0.2707 0.2004 0.053 Uiso 1 1 calc R . . C16 C -0.4033(5) 0.19084(12) 0.1896(2) 0.0417(6) Uani 1 1 d . . . H16 H -0.4227 0.1702 0.2672 0.050 Uiso 1 1 calc R . . C21 C 0.2114(5) 0.00946(12) 0.25693(19) 0.0386(6) Uani 1 1 d . A . N22 N 0.3157(4) 0.00048(10) 0.15019(15) 0.0424(5) Uani 1 1 d . . . C23 C 0.5067(5) -0.04998(13) 0.1486(2) 0.0458(6) Uani 1 1 d . A . H23 H 0.5818 -0.0573 0.0740 0.055 Uiso 1 1 calc R . . C24 C 0.6013(5) -0.09229(12) 0.2503(2) 0.0454(6) Uani 1 1 d . . . H24 H 0.7377 -0.1277 0.2453 0.054 Uiso 1 1 calc R A . C25 C 0.4938(5) -0.08190(12) 0.3586(2) 0.0462(7) Uani 1 1 d . A -1 H25 H 0.5568 -0.1097 0.4300 0.055 Uiso 0.968(3) 1 calc PR B -1 C26 C 0.2930(5) -0.03060(13) 0.36250(19) 0.0435(6) Uani 1 1 d . . . H26 H 0.2131 -0.0230 0.4358 0.052 Uiso 1 1 calc R A . Cl25 Cl 0.618(4) -0.1199(11) 0.4673(18) 0.056(9) Uiso 0.032(3) 1 d P B -2 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 F12 0.0581(10) 0.0560(10) 0.0417(8) 0.0024(6) 0.0227(7) 0.0095(7) O1 0.0671(12) 0.0517(11) 0.0368(9) 0.0008(7) 0.0191(9) 0.0083(9) C1 0.0422(15) 0.0410(13) 0.0353(13) -0.0023(10) 0.0098(11) -0.0017(12) N1 0.0459(13) 0.0457(12) 0.0368(11) 0.0008(9) 0.0164(10) 0.0045(10) C11 0.0416(15) 0.0385(15) 0.0367(12) -0.0007(10) 0.0091(11) -0.0038(11) C12 0.0449(15) 0.0464(15) 0.0360(13) -0.0045(11) 0.0166(11) 0.0004(12) C13 0.0553(17) 0.0476(16) 0.0356(12) 0.0027(11) 0.0132(11) -0.0011(13) C14 0.0501(16) 0.0433(15) 0.0424(13) 0.0017(11) 0.0110(11) 0.0029(12) C15 0.0470(15) 0.0489(15) 0.0373(13) -0.0017(11) 0.0122(11) -0.0002(13) C16 0.0455(15) 0.0486(15) 0.0338(12) -0.0009(10) 0.0143(11) -0.0017(12) C21 0.0390(14) 0.0397(13) 0.0386(13) -0.0001(10) 0.0109(10) -0.0069(11) N22 0.0437(12) 0.0452(13) 0.0403(11) -0.0011(9) 0.0133(9) 0.0006(10) C23 0.0464(16) 0.0485(15) 0.0452(14) -0.0051(11) 0.0153(12) 0.0001(13) C24 0.0438(15) 0.0450(15) 0.0486(14) -0.0001(11) 0.0113(11) 0.0002(12) C25 0.0464(16) 0.0462(15) 0.0462(15) 0.0063(11) 0.0077(12) -0.0008(13) C26 0.0466(16) 0.0483(16) 0.0369(12) -0.0006(11) 0.0108(11) -0.0048(13) _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 F12 C12 1.370(2) . ? O1 C1 1.222(2) . ? C1 N1 1.358(3) . ? C1 C21 1.505(3) . ? N1 C11 1.402(3) . ? N1 H1 0.92(2) . ? C11 C16 1.388(3) . ? C11 C12 1.389(3) . ? C12 C13 1.365(3) . ? C13 C14 1.383(3) . ? C13 H13 0.9500 . ? C14 C15 1.382(3) . ? C14 H14 0.9500 . ? C15 C16 1.390(3) . ? C15 H15 0.9500 . ? C16 H16 0.9500 . ? C21 N22 1.348(2) . ? C21 C26 1.384(3) . ? N22 C23 1.334(3) . ? C23 C24 1.386(3) . ? C23 H23 0.9500 . ? C24 C25 1.375(3) . ? C24 H24 0.9500 . ? C25 C26 1.381(3) . ? C25 H25 0.9500 . ? C26 H26 0.9500 . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag O1 C1 N1 125.1(2) . . ? O1 C1 C21 122.2(2) . . ? N1 C1 C21 112.67(19) . . ? C1 N1 C11 128.9(2) . . ? C1 N1 H1 111.7(14) . . ? C11 N1 H1 119.2(14) . . ? C16 C11 C12 117.1(2) . . ? C16 C11 N1 125.5(2) . . ? C12 C11 N1 117.4(2) . . ? C13 C12 F12 119.53(19) . . ? C13 C12 C11 123.6(2) . . ? F12 C12 C11 116.9(2) . . ? C12 C13 C14 118.6(2) . . ? C12 C13 H13 120.7 . . ? C14 C13 H13 120.7 . . ? C15 C14 C13 119.8(2) . . ? C15 C14 H14 120.1 . . ? C13 C14 H14 120.1 . . ? C14 C15 C16 120.7(2) . . ? C14 C15 H15 119.6 . . ? C16 C15 H15 119.6 . . ? C11 C16 C15 120.2(2) . . ? C11 C16 H16 119.9 . . ? C15 C16 H16 119.9 . . ? N22 C21 C26 123.3(2) . . ? N22 C21 C1 116.5(2) . . ? C26 C21 C1 120.2(2) . . ? C23 N22 C21 117.08(19) . . ? N22 C23 C24 123.4(2) . . ? N22 C23 H23 118.3 . . ? C24 C23 H23 118.3 . . ? C25 C24 C23 118.6(2) . . ? C25 C24 H24 120.7 . . ? C23 C24 H24 120.7 . . ? C24 C25 C26 119.3(2) . . ? C24 C25 H25 120.3 . . ? C26 C25 H25 120.3 . . ? C25 C26 C21 118.3(2) . . ? C25 C26 H26 120.8 . . ? C21 C26 H26 120.8 . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag O1 C1 N1 C11 4.5(4) . . . . ? C21 C1 N1 C11 -174.2(2) . . . . ? C1 N1 C11 C16 -11.2(4) . . . . ? C1 N1 C11 C12 168.2(2) . . . . ? C16 C11 C12 C13 0.5(4) . . . . ? N1 C11 C12 C13 -179.0(2) . . . . ? C16 C11 C12 F12 179.63(19) . . . . ? N1 C11 C12 F12 0.1(3) . . . . ? F12 C12 C13 C14 -179.4(2) . . . . ? C11 C12 C13 C14 -0.3(4) . . . . ? C12 C13 C14 C15 0.0(4) . . . . ? C13 C14 C15 C16 0.2(4) . . . . ? C12 C11 C16 C15 -0.3(3) . . . . ? N1 C11 C16 C15 179.1(2) . . . . ? C14 C15 C16 C11 0.0(4) . . . . ? O1 C1 C21 N22 -177.9(2) . . . . ? N1 C1 C21 N22 0.8(3) . . . . ? O1 C1 C21 C26 1.1(4) . . . . ? N1 C1 C21 C26 179.9(2) . . . . ? C26 C21 N22 C23 0.1(3) . . . . ? C1 C21 N22 C23 179.14(19) . . . . ? C21 N22 C23 C24 -0.4(4) . . . . ? N22 C23 C24 C25 -0.1(4) . . . . ? C23 C24 C25 C26 0.9(4) . . . . ? C24 C25 C26 C21 -1.2(3) . . . . ? N22 C21 C26 C25 0.7(4) . . . . ? C1 C21 C26 C25 -178.3(2) . . . . ? loop_ _geom_hbond_atom_site_label_D _geom_hbond_atom_site_label_H _geom_hbond_atom_site_label_A _geom_hbond_distance_DH _geom_hbond_distance_HA _geom_hbond_distance_DA _geom_hbond_angle_DHA _geom_hbond_site_symmetry_A _geom_hbond_publ_flag # # Hydrogen bonding scheme # ======== ======= ====== # # D H A D-H H...A D...A D-H...A symm publ # - - - --- ----- ----- ------- ---- ---- N1 H1 F12 0.92(2) 2.29(2) 2.654(2) 102.8(16) . yes N1 H1 N22 0.92(2) 2.09(2) 2.630(3) 116.2(17) . yes C14 H14 O1 0.95 2.55 3.298(3) 136 4_565 yes C16 H16 O1 0.95 2.37 2.950(3) 119 . yes #===================================================================== # Attachment '- NxxF-Final04.cif' # File 9-16 c:\x\9-16\9-isomers\NxxF-Final01.cif #============================================================ data_NppF_[9-08] _database_code_depnum_ccdc_archive 'CCDC 781752' #TrackingRef '- NxxF-Final04.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common NppF _chemical_melting_point 409 _chemical_formula_moiety 'C12 H9 F N2 O' _chemical_formula_sum 'C12 H9 F N2 O' _chemical_formula_weight 216.21 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' F F 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Triclinic _symmetry_space_group_name_H-M 'P -1' _symmetry_space_group_name_Hall '-P 1' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 5.4260(2) _cell_length_b 7.4928(3) _cell_length_c 24.0074(9) _cell_angle_alpha 80.9694(18) _cell_angle_beta 90.041(2) _cell_angle_gamma 90.243(2) _cell_volume 963.94(6) _cell_formula_units_Z 4 _cell_measurement_temperature 200(2) _cell_measurement_reflns_used 7481 _cell_measurement_theta_min 2.55 _cell_measurement_theta_max 27.5 _exptl_crystal_description block _exptl_crystal_colour colourless _exptl_crystal_size_max 0.25 _exptl_crystal_size_mid 0.10 _exptl_crystal_size_min 0.08 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.490 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 448 _exptl_absorpt_coefficient_mu 0.111 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.973 _exptl_absorpt_correction_T_max 0.991 _exptl_absorpt_process_details '(SORTAV; Blessing, 1995)' _exptl_special_details ; ? ; _diffrn_ambient_temperature 200(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed X-ray tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device 'Nonius KappaCCD' _diffrn_measurement_method '\f, \w scans with \k offsets' _diffrn_standards_number ? _diffrn_standards_decay_% ? _diffrn_reflns_number 4341 _diffrn_reflns_av_R_equivalents 0.0000 _diffrn_reflns_av_sigmaI/netI 0.0583 _diffrn_reflns_limit_h_min -7 _diffrn_reflns_limit_h_max 7 _diffrn_reflns_limit_k_min -9 _diffrn_reflns_limit_k_max 9 _diffrn_reflns_limit_l_min -31 _diffrn_reflns_limit_l_max 31 _diffrn_reflns_theta_min 2.58 _diffrn_reflns_theta_max 27.55 _diffrn_measured_fraction_theta_max 0.982 _diffrn_reflns_theta_full 27.55 _diffrn_measured_fraction_theta_full 0.982 _reflns_number_total 4341 _reflns_number_gt 3270 _reflns_threshold_expression I>2\s(I) _computing_data_collection 'kappaCCD Server software (Nonius, 1997)' _computing_cell_refinement 'DENZO-SMN (Otwinowski and Minor, 1997)' _computing_data_reduction 'DENZO-SMN (Otwinowski and Minor, 1997)' _computing_structure_solution 'SHELXS97 (Sheldrick, 2008)' _computing_structure_refinement 'SHELXL97 (Sheldrick, 2008) and SORTX (McArdle, 1995)' _computing_molecular_graphics 'PLATON (Spek, 2003)' _computing_publication_material 'SHELXL97 and PREP8 (Ferguson, 1998)' _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 'w=1/[\s^2^(Fo^2^)+(0.0676P)^2^+0.2313P] 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 SHELXL _refine_ls_extinction_coef 0.018(5) _refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^ _refine_ls_number_reflns 4341 _refine_ls_number_parameters 299 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0760 _refine_ls_R_factor_gt 0.0510 _refine_ls_wR_factor_ref 0.1420 _refine_ls_wR_factor_gt 0.1233 _refine_ls_goodness_of_fit_ref 1.034 _refine_ls_restrained_S_all 1.034 _refine_ls_shift/su_max 0.000 _refine_ls_shift/su_mean 0.000 _refine_diff_density_max 0.231 _refine_diff_density_min -0.232 _refine_diff_density_rms 0.049 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 F14A F 0.8371(2) 0.57432(19) -0.24174(5) 0.0440(4) Uani 1 1 d . . . O1A O 0.3904(3) 0.2496(2) -0.00080(7) 0.0445(4) Uani 1 1 d . . . C1A C 0.6036(4) 0.2261(3) 0.01610(9) 0.0311(5) Uani 1 1 d . . . N1A N 0.8045(3) 0.2674(2) -0.01707(7) 0.0316(4) Uani 1 1 d . . . H1A H 0.945(5) 0.255(3) 0.0009(10) 0.037(6) Uiso 1 1 d . . . C11A C 0.8038(4) 0.3457(3) -0.07495(8) 0.0288(4) Uani 1 1 d . . . C12A C 0.6159(4) 0.3139(3) -0.11168(9) 0.0321(5) Uani 1 1 d . . . H12A H 0.4793 0.2399 -0.0981 0.038 Uiso 1 1 calc R . . C13A C 0.6277(4) 0.3900(3) -0.16811(9) 0.0327(5) Uani 1 1 d . . . H13A H 0.5004 0.3687 -0.1935 0.039 Uiso 1 1 calc R . . C14A C 0.8274(4) 0.4970(3) -0.18670(8) 0.0315(5) Uani 1 1 d . . . C15A C 1.0174(4) 0.5293(3) -0.15161(9) 0.0334(5) Uani 1 1 d . . . H15A H 1.1540 0.6025 -0.1657 0.040 Uiso 1 1 calc R . . C16A C 1.0052(4) 0.4525(3) -0.09523(9) 0.0312(5) Uani 1 1 d . . . H16A H 1.1348 0.4729 -0.0703 0.037 Uiso 1 1 calc R . . C21A C 0.6542(4) 0.1491(3) 0.07653(8) 0.0291(4) Uani 1 1 d . . . C22A C 0.8624(4) 0.0490(3) 0.09491(9) 0.0316(5) Uani 1 1 d . . . H22A H 0.9881 0.0293 0.0691 0.038 Uiso 1 1 calc R . . C23A C 0.8830(4) -0.0217(3) 0.15181(9) 0.0350(5) Uani 1 1 d . . . H23A H 1.0261 -0.0895 0.1640 0.042 Uiso 1 1 calc R . . N24A N 0.7129(3) 0.0003(3) 0.19045(8) 0.0374(4) Uani 1 1 d . . . C25A C 0.5156(4) 0.0988(3) 0.17215(9) 0.0349(5) Uani 1 1 d . . . H25A H 0.3938 0.1178 0.1990 0.042 Uiso 1 1 calc R . . C26A C 0.4781(4) 0.1746(3) 0.11652(9) 0.0325(5) Uani 1 1 d . . . H26A H 0.3341 0.2431 0.1058 0.039 Uiso 1 1 calc R . . F14B F 0.6631(2) 0.3394(2) 0.27260(5) 0.0475(4) Uani 1 1 d . . . O1B O 1.1072(3) 0.2616(2) 0.52136(7) 0.0438(4) Uani 1 1 d . . . C1B C 0.8947(4) 0.2440(3) 0.53925(9) 0.0333(5) Uani 1 1 d . . . N1B N 0.6948(3) 0.2482(3) 0.50527(8) 0.0342(4) Uani 1 1 d . . . H1B H 0.560(5) 0.249(3) 0.5205(11) 0.041(7) Uiso 1 1 d . . . C11B C 0.6954(4) 0.2726(3) 0.44531(9) 0.0317(5) Uani 1 1 d . . . C12B C 0.8836(4) 0.2058(3) 0.41511(9) 0.0337(5) Uani 1 1 d . . . H12B H 1.0195 0.1449 0.4344 0.040 Uiso 1 1 calc R . . C13B C 0.8718(4) 0.2285(3) 0.35651(9) 0.0346(5) Uani 1 1 d . . . H13B H 0.9986 0.1830 0.3354 0.042 Uiso 1 1 calc R . . C14B C 0.6740(4) 0.3176(3) 0.32973(9) 0.0349(5) Uani 1 1 d . . . C15B C 0.4854(4) 0.3856(3) 0.35848(9) 0.0357(5) Uani 1 1 d . . . H15B H 0.3512 0.4476 0.3388 0.043 Uiso 1 1 calc R . . C16B C 0.4973(4) 0.3610(3) 0.41692(9) 0.0336(5) Uani 1 1 d . . . H16B H 0.3683 0.4052 0.4377 0.040 Uiso 1 1 calc R . . C21B C 0.8440(4) 0.2148(3) 0.60138(9) 0.0309(5) Uani 1 1 d . . . C22B C 0.6361(4) 0.1252(3) 0.62607(9) 0.0345(5) Uani 1 1 d . . . H22B H 0.5122 0.0819 0.6035 0.041 Uiso 1 1 calc R . . C23B C 0.6147(4) 0.1009(3) 0.68436(9) 0.0376(5) Uani 1 1 d . . . H23B H 0.4723 0.0404 0.7010 0.045 Uiso 1 1 calc R . . N24B N 0.7821(4) 0.1575(3) 0.71856(8) 0.0398(5) Uani 1 1 d . . . C25B C 0.9799(4) 0.2428(3) 0.69426(9) 0.0387(5) Uani 1 1 d . . . H25B H 1.1010 0.2840 0.7179 0.046 Uiso 1 1 calc R . . C26B C 1.0189(4) 0.2749(3) 0.63658(9) 0.0344(5) Uani 1 1 d . . . H26B H 1.1626 0.3370 0.6213 0.041 Uiso 1 1 calc R . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 F14A 0.0424(7) 0.0612(9) 0.0250(7) 0.0037(6) 0.0002(5) -0.0024(6) O1A 0.0315(8) 0.0694(11) 0.0305(9) -0.0009(8) -0.0030(6) 0.0042(8) C1A 0.0319(11) 0.0362(11) 0.0250(11) -0.0044(8) -0.0006(8) 0.0025(9) N1A 0.0282(9) 0.0395(10) 0.0262(9) -0.0016(8) -0.0018(7) -0.0003(7) C11A 0.0302(10) 0.0323(10) 0.0237(10) -0.0039(8) 0.0016(8) 0.0028(8) C12A 0.0293(10) 0.0350(11) 0.0315(11) -0.0042(9) 0.0010(8) -0.0031(8) C13A 0.0302(10) 0.0400(12) 0.0284(11) -0.0066(9) -0.0028(8) 0.0008(9) C14A 0.0364(11) 0.0351(11) 0.0215(10) 0.0004(8) 0.0021(8) 0.0039(9) C15A 0.0316(11) 0.0373(11) 0.0302(12) -0.0022(9) 0.0026(8) -0.0023(9) C16A 0.0313(10) 0.0363(11) 0.0263(11) -0.0054(9) -0.0031(8) 0.0015(9) C21A 0.0307(10) 0.0304(10) 0.0257(11) -0.0029(8) -0.0016(8) -0.0040(8) C22A 0.0312(10) 0.0346(11) 0.0290(11) -0.0049(9) 0.0020(8) -0.0013(9) C23A 0.0328(11) 0.0358(11) 0.0347(12) 0.0000(9) -0.0036(9) 0.0015(9) N24A 0.0375(10) 0.0432(11) 0.0297(10) 0.0002(8) -0.0021(8) -0.0016(8) C25A 0.0328(11) 0.0423(12) 0.0289(12) -0.0037(9) 0.0025(8) -0.0019(9) C26A 0.0304(10) 0.0367(11) 0.0301(11) -0.0038(9) -0.0003(8) 0.0002(9) F14B 0.0442(8) 0.0732(10) 0.0243(7) -0.0049(6) -0.0011(5) 0.0008(7) O1B 0.0351(8) 0.0648(11) 0.0308(9) -0.0058(8) 0.0048(6) -0.0053(8) C1B 0.0361(11) 0.0363(11) 0.0267(11) -0.0026(9) 0.0017(8) -0.0001(9) N1B 0.0304(10) 0.0461(11) 0.0254(10) -0.0036(8) 0.0025(7) 0.0000(8) C11B 0.0335(11) 0.0362(11) 0.0249(11) -0.0033(9) -0.0004(8) -0.0051(9) C12B 0.0341(11) 0.0376(11) 0.0292(11) -0.0045(9) -0.0024(8) 0.0015(9) C13B 0.0332(11) 0.0421(12) 0.0299(11) -0.0098(9) 0.0037(8) -0.0008(9) C14B 0.0367(11) 0.0448(12) 0.0226(11) -0.0042(9) 0.0008(8) -0.0057(9) C15B 0.0309(11) 0.0418(12) 0.0334(12) -0.0030(9) -0.0016(9) -0.0006(9) C16B 0.0319(11) 0.0406(12) 0.0283(11) -0.0055(9) 0.0015(8) -0.0004(9) C21B 0.0331(10) 0.0338(11) 0.0253(11) -0.0025(8) 0.0004(8) 0.0033(9) C22B 0.0328(11) 0.0408(12) 0.0296(11) -0.0044(9) -0.0011(8) -0.0012(9) C23B 0.0356(11) 0.0438(12) 0.0315(12) -0.0007(10) 0.0034(9) -0.0021(10) N24B 0.0404(10) 0.0499(11) 0.0280(10) -0.0033(8) -0.0002(8) 0.0004(9) C25B 0.0371(11) 0.0481(13) 0.0316(12) -0.0089(10) -0.0046(9) -0.0013(10) C26B 0.0318(11) 0.0389(12) 0.0324(12) -0.0049(9) 0.0009(9) -0.0005(9) _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 F14A C14A 1.358(2) . ? O1A C1A 1.229(2) . ? C1A N1A 1.356(3) . ? C1A C21A 1.500(3) . ? N1A C11A 1.421(3) . ? N1A H1A 0.88(3) . ? C11A C12A 1.392(3) . ? C11A C16A 1.394(3) . ? C12A C13A 1.386(3) . ? C12A H12A 0.9500 . ? C13A C14A 1.378(3) . ? C13A H13A 0.9500 . ? C14A C15A 1.376(3) . ? C15A C16A 1.387(3) . ? C15A H15A 0.9500 . ? C16A H16A 0.9500 . ? C21A C26A 1.390(3) . ? C21A C22A 1.392(3) . ? C22A C23A 1.390(3) . ? C22A H22A 0.9500 . ? C23A N24A 1.338(3) . ? C23A H23A 0.9500 . ? N24A C25A 1.337(3) . ? C25A C26A 1.382(3) . ? C25A H25A 0.9500 . ? C26A H26A 0.9500 . ? F14B C14B 1.357(2) . ? O1B C1B 1.230(3) . ? C1B N1B 1.354(3) . ? C1B C21B 1.499(3) . ? N1B C11B 1.422(3) . ? N1B H1B 0.82(3) . ? C11B C16B 1.387(3) . ? C11B C12B 1.392(3) . ? C12B C13B 1.392(3) . ? C12B H12B 0.9500 . ? C13B C14B 1.372(3) . ? C13B H13B 0.9500 . ? C14B C15B 1.378(3) . ? C15B C16B 1.387(3) . ? C15B H15B 0.9500 . ? C16B H16B 0.9500 . ? C21B C26B 1.390(3) . ? C21B C22B 1.394(3) . ? C22B C23B 1.388(3) . ? C22B H22B 0.9500 . ? C23B N24B 1.336(3) . ? C23B H23B 0.9500 . ? N24B C25B 1.334(3) . ? C25B C26B 1.384(3) . ? C25B H25B 0.9500 . ? C26B H26B 0.9500 . ? 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 O1A C1A N1A 123.68(19) . . ? O1A C1A C21A 120.38(18) . . ? N1A C1A C21A 115.94(18) . . ? C1A N1A C11A 126.30(18) . . ? C1A N1A H1A 114.5(16) . . ? C11A N1A H1A 118.8(16) . . ? C12A C11A C16A 119.79(19) . . ? C12A C11A N1A 122.46(18) . . ? C16A C11A N1A 117.71(18) . . ? C13A C12A C11A 120.06(19) . . ? C13A C12A H12A 120.0 . . ? C11A C12A H12A 120.0 . . ? C14A C13A C12A 118.77(19) . . ? C14A C13A H13A 120.6 . . ? C12A C13A H13A 120.6 . . ? F14A C14A C15A 118.59(18) . . ? F14A C14A C13A 118.86(18) . . ? C15A C14A C13A 122.55(19) . . ? C14A C15A C16A 118.49(19) . . ? C14A C15A H15A 120.8 . . ? C16A C15A H15A 120.8 . . ? C15A C16A C11A 120.33(19) . . ? C15A C16A H16A 119.8 . . ? C11A C16A H16A 119.8 . . ? C26A C21A C22A 117.83(19) . . ? C26A C21A C1A 117.89(18) . . ? C22A C21A C1A 124.24(19) . . ? C23A C22A C21A 118.75(19) . . ? C23A C22A H22A 120.6 . . ? C21A C22A H22A 120.6 . . ? N24A C23A C22A 123.77(19) . . ? N24A C23A H23A 118.1 . . ? C22A C23A H23A 118.1 . . ? C25A N24A C23A 116.65(19) . . ? N24A C25A C26A 123.9(2) . . ? N24A C25A H25A 118.0 . . ? C26A C25A H25A 118.0 . . ? C25A C26A C21A 119.06(19) . . ? C25A C26A H26A 120.5 . . ? C21A C26A H26A 120.5 . . ? O1B C1B N1B 123.3(2) . . ? O1B C1B C21B 120.69(19) . . ? N1B C1B C21B 116.01(18) . . ? C1B N1B C11B 126.49(19) . . ? C1B N1B H1B 116.6(18) . . ? C11B N1B H1B 116.5(18) . . ? C16B C11B C12B 119.90(19) . . ? C16B C11B N1B 118.10(19) . . ? C12B C11B N1B 121.96(18) . . ? C13B C12B C11B 119.71(19) . . ? C13B C12B H12B 120.1 . . ? C11B C12B H12B 120.1 . . ? C14B C13B C12B 118.89(19) . . ? C14B C13B H13B 120.6 . . ? C12B C13B H13B 120.6 . . ? F14B C14B C13B 118.70(19) . . ? F14B C14B C15B 118.61(19) . . ? C13B C14B C15B 122.69(19) . . ? C14B C15B C16B 118.1(2) . . ? C14B C15B H15B 120.9 . . ? C16B C15B H15B 120.9 . . ? C11B C16B C15B 120.7(2) . . ? C11B C16B H16B 119.7 . . ? C15B C16B H16B 119.7 . . ? C26B C21B C22B 118.14(19) . . ? C26B C21B C1B 118.00(19) . . ? C22B C21B C1B 123.82(19) . . ? C23B C22B C21B 118.3(2) . . ? C23B C22B H22B 120.8 . . ? C21B C22B H22B 120.8 . . ? N24B C23B C22B 124.0(2) . . ? N24B C23B H23B 118.0 . . ? C22B C23B H23B 118.0 . . ? C25B N24B C23B 116.89(19) . . ? N24B C25B C26B 123.8(2) . . ? N24B C25B H25B 118.1 . . ? C26B C25B H25B 118.1 . . ? C25B C26B C21B 118.8(2) . . ? C25B C26B H26B 120.6 . . ? C21B C26B H26B 120.6 . . ? 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 O1A C1A N1A C11A 1.3(3) . . . . ? C21A C1A N1A C11A -178.25(18) . . . . ? C1A N1A C11A C12A -31.5(3) . . . . ? C1A N1A C11A C16A 150.9(2) . . . . ? C16A C11A C12A C13A -0.8(3) . . . . ? N1A C11A C12A C13A -178.28(18) . . . . ? C11A C12A C13A C14A -0.2(3) . . . . ? C12A C13A C14A F14A -178.83(18) . . . . ? C12A C13A C14A C15A 1.0(3) . . . . ? F14A C14A C15A C16A 179.00(18) . . . . ? C13A C14A C15A C16A -0.8(3) . . . . ? C14A C15A C16A C11A -0.2(3) . . . . ? C12A C11A C16A C15A 0.9(3) . . . . ? N1A C11A C16A C15A 178.58(18) . . . . ? O1A C1A C21A C26A -26.1(3) . . . . ? N1A C1A C21A C26A 153.4(2) . . . . ? O1A C1A C21A C22A 151.8(2) . . . . ? N1A C1A C21A C22A -28.7(3) . . . . ? C26A C21A C22A C23A 0.6(3) . . . . ? C1A C21A C22A C23A -177.27(19) . . . . ? C21A C22A C23A N24A 0.2(3) . . . . ? C22A C23A N24A C25A -1.0(3) . . . . ? C23A N24A C25A C26A 1.0(3) . . . . ? N24A C25A C26A C21A -0.2(3) . . . . ? C22A C21A C26A C25A -0.6(3) . . . . ? C1A C21A C26A C25A 177.41(19) . . . . ? O1B C1B N1B C11B 0.1(4) . . . . ? C21B C1B N1B C11B -179.52(19) . . . . ? C1B N1B C11B C16B -148.1(2) . . . . ? C1B N1B C11B C12B 33.9(3) . . . . ? C16B C11B C12B C13B 0.1(3) . . . . ? N1B C11B C12B C13B 178.0(2) . . . . ? C11B C12B C13B C14B 0.3(3) . . . . ? C12B C13B C14B F14B -179.99(19) . . . . ? C12B C13B C14B C15B -0.1(3) . . . . ? F14B C14B C15B C16B 179.4(2) . . . . ? C13B C14B C15B C16B -0.5(3) . . . . ? C12B C11B C16B C15B -0.7(3) . . . . ? N1B C11B C16B C15B -178.7(2) . . . . ? C14B C15B C16B C11B 0.9(3) . . . . ? O1B C1B C21B C26B 24.1(3) . . . . ? N1B C1B C21B C26B -156.2(2) . . . . ? O1B C1B C21B C22B -153.5(2) . . . . ? N1B C1B C21B C22B 26.1(3) . . . . ? C26B C21B C22B C23B 0.0(3) . . . . ? C1B C21B C22B C23B 177.65(19) . . . . ? C21B C22B C23B N24B -0.3(3) . . . . ? C22B C23B N24B C25B 0.3(3) . . . . ? C23B N24B C25B C26B 0.1(3) . . . . ? N24B C25B C26B C21B -0.3(3) . . . . ? C22B C21B C26B C25B 0.3(3) . . . . ? C1B C21B C26B C25B -177.49(19) . . . . ? loop_ _geom_hbond_atom_site_label_D _geom_hbond_atom_site_label_H _geom_hbond_atom_site_label_A _geom_hbond_distance_DH _geom_hbond_distance_HA _geom_hbond_distance_DA _geom_hbond_angle_DHA _geom_hbond_site_symmetry_A _geom_hbond_publ_flag # # Hydrogen bonding scheme # ======== ======= ====== # # D H A D-H H...A D...A D-H...A symm publ # - - - --- ----- ----- ------- ---- ---- N1A H1A O1A 0.88(3) 2.42(3) 3.203(2) 150(2) 1_655 yes N1B H1B O1B 0.82(3) 2.46(3) 3.216(2) 154(2) 1_455 yes C12A H12A O1A 0.95 2.40 2.900(3) 113 . yes C12B H12B O1B 0.95 2.43 2.912(3) 111 . yes C16A H16A O1A 0.95 2.58 3.280(2) 131 1_655 yes C16B H16B O1B 0.95 2.55 3.275(3) 133 1_455 yes # Cg1 and Cg2 are the C~6~ aromatic ring centroids located # at sites X and a_xyz # Complete details for the C-H...\p(arene) interaction #========================================================================= data_NpmF_[9-17] _database_code_depnum_ccdc_archive 'CCDC 781753' #TrackingRef '- NxxF-Final04.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common NpmF _chemical_melting_point 405 _chemical_formula_moiety 'C12 H9 F N2 O' _chemical_formula_sum 'C12 H9 F N2 O' _chemical_formula_weight 216.21 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' F F 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Monoclinic _symmetry_space_group_name_H-M 'C c' _symmetry_space_group_name_Hall 'C -2yc' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' 'x, -y, z+1/2' 'x+1/2, y+1/2, z' 'x+1/2, -y+1/2, z+1/2' _cell_length_a 11.0723(7) _cell_length_b 12.8655(8) _cell_length_c 7.9596(3) _cell_angle_alpha 90.00 _cell_angle_beta 114.444(4) _cell_angle_gamma 90.00 _cell_volume 1032.22(10) _cell_formula_units_Z 4 _cell_measurement_temperature 150(2) _cell_measurement_reflns_used 5211 _cell_measurement_theta_min 2.55 _cell_measurement_theta_max 27.5 _exptl_crystal_description block _exptl_crystal_colour colourless _exptl_crystal_size_max 0.36 _exptl_crystal_size_mid 0.16 _exptl_crystal_size_min 0.16 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.391 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 448 _exptl_absorpt_coefficient_mu 0.103 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.964 _exptl_absorpt_correction_T_max 0.984 _exptl_absorpt_process_details '(SORTAV; Blessing, 1995)' _exptl_special_details ; ? ; _diffrn_ambient_temperature 150(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed X-ray tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device 'Nonius KappaCCD' _diffrn_measurement_method '\f, \w scans with \k offsets' _diffrn_standards_number ? _diffrn_standards_decay_% ? _diffrn_reflns_number 3643 _diffrn_reflns_av_R_equivalents 0.0777 _diffrn_reflns_av_sigmaI/netI 0.0590 _diffrn_reflns_limit_h_min -14 _diffrn_reflns_limit_h_max 10 _diffrn_reflns_limit_k_min -15 _diffrn_reflns_limit_k_max 16 _diffrn_reflns_limit_l_min -10 _diffrn_reflns_limit_l_max 10 _diffrn_reflns_theta_min 2.57 _diffrn_reflns_theta_max 27.51 _diffrn_measured_fraction_theta_max 0.987 _diffrn_reflns_theta_full 27.51 _diffrn_measured_fraction_theta_full 0.987 _reflns_number_total 1176 _reflns_number_gt 989 _reflns_threshold_expression I>2\s(I) _computing_data_collection 'kappaCCD Server software (Nonius, 1997)' _computing_cell_refinement 'DENZO-SMN (Otwinowski and Minor, 1997)' _computing_data_reduction 'DENZO-SMN (Otwinowski and Minor, 1997)' _computing_structure_solution 'SHELXS97 (Sheldrick, 2008)' _computing_structure_refinement 'SHELXL97 (Sheldrick, 2008) and SORTX (McArdle, 1995)' _computing_molecular_graphics 'PLATON (Spek, 2009)' _computing_publication_material 'SHELXL97 and PREP8 (Ferguson, 1998)' _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 'w=1/[\s^2^(Fo^2^)+(0.0568P)^2^+0.2699P] 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 SHELXL _refine_ls_extinction_coef 0.012(3) _refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^ #_refine_ls_abs_structure_details '(Flack, 1983)' #_refine_ls_abs_structure_Flack 0(1) _refine_ls_number_reflns 1176 _refine_ls_number_parameters 150 _refine_ls_number_restraints 2 _refine_ls_R_factor_all 0.0553 _refine_ls_R_factor_gt 0.0418 _refine_ls_wR_factor_ref 0.1133 _refine_ls_wR_factor_gt 0.1021 _refine_ls_goodness_of_fit_ref 1.038 _refine_ls_restrained_S_all 1.037 _refine_ls_shift/su_max 0.000 _refine_ls_shift/su_mean 0.000 _refine_diff_density_max 0.179 _refine_diff_density_min -0.252 _refine_diff_density_rms 0.046 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 F13 F -0.0826(2) 0.02418(17) 0.1514(3) 0.0523(6) Uani 1 1 d . . . O1 O 0.5293(2) 0.08487(17) 0.5847(3) 0.0410(6) Uani 1 1 d . . . C1 C 0.5016(3) -0.0048(2) 0.5304(4) 0.0298(6) Uani 1 1 d . . . N1 N 0.3822(3) -0.0334(2) 0.3976(4) 0.0322(6) Uani 1 1 d . . . H1 H 0.363(4) -0.100(3) 0.372(5) 0.045(11) Uiso 1 1 d . . . C11 C 0.2734(3) 0.0339(2) 0.3082(4) 0.0311(7) Uani 1 1 d . . . C12 C 0.1473(3) -0.0021(3) 0.2746(4) 0.0328(7) Uani 1 1 d . . . H12 H 0.1354 -0.0694 0.3147 0.039 Uiso 1 1 calc R . . C13 C 0.0401(3) 0.0609(3) 0.1827(4) 0.0378(7) Uani 1 1 d . . . C14 C 0.0513(4) 0.1601(3) 0.1262(4) 0.0417(8) Uani 1 1 d . . . H14 H -0.0244 0.2027 0.0651 0.050 Uiso 1 1 calc R . . C15 C 0.1778(4) 0.1952(3) 0.1623(4) 0.0415(8) Uani 1 1 d . . . H15 H 0.1887 0.2633 0.1245 0.050 Uiso 1 1 calc R . . C16 C 0.2887(4) 0.1342(2) 0.2517(4) 0.0363(7) Uani 1 1 d . . . H16 H 0.3745 0.1600 0.2746 0.044 Uiso 1 1 calc R . . C21 C 0.5989(3) -0.0909(2) 0.6106(4) 0.0292(6) Uani 1 1 d . . . C22 C 0.6956(3) -0.0815(2) 0.7896(4) 0.0328(7) Uani 1 1 d . . . H22 H 0.7016 -0.0202 0.8590 0.039 Uiso 1 1 calc R . . C23 C 0.7830(3) -0.1627(2) 0.8652(4) 0.0353(7) Uani 1 1 d . . . H23 H 0.8486 -0.1551 0.9878 0.042 Uiso 1 1 calc R . . N24 N 0.7810(3) -0.2516(2) 0.7764(3) 0.0340(6) Uani 1 1 d . . . C25 C 0.6898(3) -0.2587(2) 0.6019(4) 0.0326(7) Uani 1 1 d . . . H25 H 0.6882 -0.3201 0.5346 0.039 Uiso 1 1 calc R . . C26 C 0.5982(3) -0.1817(2) 0.5140(4) 0.0317(7) Uani 1 1 d . . . H26 H 0.5356 -0.1905 0.3898 0.038 Uiso 1 1 calc R . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 F13 0.0273(11) 0.0527(14) 0.0699(14) -0.0141(11) 0.0131(10) 0.0035(10) O1 0.0386(13) 0.0235(11) 0.0553(14) -0.0067(9) 0.0138(11) -0.0025(9) C1 0.0308(16) 0.0229(14) 0.0390(15) -0.0014(12) 0.0179(13) 0.0001(12) N1 0.0275(14) 0.0243(13) 0.0422(15) -0.0026(11) 0.0120(11) 0.0012(11) C11 0.0288(16) 0.0287(15) 0.0353(15) -0.0034(12) 0.0128(12) 0.0043(13) C12 0.0302(15) 0.0303(15) 0.0362(15) -0.0045(12) 0.0120(12) 0.0014(12) C13 0.0283(16) 0.0410(18) 0.0395(17) -0.0094(14) 0.0092(13) 0.0072(14) C14 0.042(2) 0.042(2) 0.0370(17) -0.0010(15) 0.0127(14) 0.0164(16) C15 0.053(2) 0.0340(17) 0.0431(19) 0.0077(14) 0.0256(17) 0.0121(16) C16 0.0406(18) 0.0301(15) 0.0430(17) 0.0015(13) 0.0220(14) 0.0026(14) C21 0.0261(15) 0.0248(14) 0.0404(17) 0.0027(11) 0.0173(13) 0.0006(12) C22 0.0291(15) 0.0287(15) 0.0397(17) -0.0041(12) 0.0133(12) -0.0018(13) C23 0.0350(17) 0.0306(15) 0.0376(16) -0.0003(13) 0.0124(12) -0.0015(14) N24 0.0292(13) 0.0283(13) 0.0418(15) 0.0039(11) 0.0121(11) 0.0015(11) C25 0.0323(17) 0.0261(14) 0.0383(16) 0.0000(12) 0.0133(13) 0.0029(12) C26 0.0314(16) 0.0277(14) 0.0345(15) 0.0000(12) 0.0122(12) 0.0016(12) _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 F13 C13 1.360(4) . ? O1 C1 1.226(4) . ? C1 N1 1.358(4) . ? C1 C21 1.492(4) . ? N1 C11 1.414(4) . ? N1 H1 0.88(4) . ? C11 C12 1.388(5) . ? C11 C16 1.399(4) . ? C12 C13 1.372(5) . ? C12 H12 0.9500 . ? C13 C14 1.376(5) . ? C14 C15 1.384(5) . ? C14 H14 0.9500 . ? C15 C16 1.381(5) . ? C15 H15 0.9500 . ? C16 H16 0.9500 . ? C21 C22 1.389(4) . ? C21 C26 1.397(4) . ? C22 C23 1.381(4) . ? C22 H22 0.9500 . ? C23 N24 1.340(4) . ? C23 H23 0.9500 . ? N24 C25 1.340(4) . ? C25 C26 1.383(4) . ? C25 H25 0.9500 . ? C26 H26 0.9500 . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag O1 C1 N1 123.4(3) . . ? O1 C1 C21 121.1(3) . . ? N1 C1 C21 115.5(3) . . ? C1 N1 C11 125.3(3) . . ? C1 N1 H1 120(3) . . ? C11 N1 H1 114(3) . . ? C12 C11 C16 119.5(3) . . ? C12 C11 N1 118.2(3) . . ? C16 C11 N1 122.3(3) . . ? C13 C12 C11 119.0(3) . . ? C13 C12 H12 120.5 . . ? C11 C12 H12 120.5 . . ? F13 C13 C12 118.1(3) . . ? F13 C13 C14 118.7(3) . . ? C12 C13 C14 123.2(3) . . ? C13 C14 C15 117.1(3) . . ? C13 C14 H14 121.5 . . ? C15 C14 H14 121.5 . . ? C16 C15 C14 122.0(3) . . ? C16 C15 H15 119.0 . . ? C14 C15 H15 119.0 . . ? C15 C16 C11 119.3(3) . . ? C15 C16 H16 120.4 . . ? C11 C16 H16 120.4 . . ? C22 C21 C26 117.6(3) . . ? C22 C21 C1 119.2(3) . . ? C26 C21 C1 123.1(3) . . ? C23 C22 C21 119.0(3) . . ? C23 C22 H22 120.5 . . ? C21 C22 H22 120.5 . . ? N24 C23 C22 124.1(3) . . ? N24 C23 H23 118.0 . . ? C22 C23 H23 118.0 . . ? C23 N24 C25 116.5(2) . . ? N24 C25 C26 123.8(3) . . ? N24 C25 H25 118.1 . . ? C26 C25 H25 118.1 . . ? C25 C26 C21 119.0(3) . . ? C25 C26 H26 120.5 . . ? C21 C26 H26 120.5 . . ? 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 C1 N1 C11 -1.9(5) . . . . ? C21 C1 N1 C11 177.2(3) . . . . ? C1 N1 C11 C12 -139.2(3) . . . . ? C1 N1 C11 C16 41.4(4) . . . . ? C16 C11 C12 C13 1.5(5) . . . . ? N1 C11 C12 C13 -177.9(3) . . . . ? C11 C12 C13 F13 -179.9(3) . . . . ? C11 C12 C13 C14 -2.0(5) . . . . ? F13 C13 C14 C15 179.3(3) . . . . ? C12 C13 C14 C15 1.4(5) . . . . ? C13 C14 C15 C16 -0.3(5) . . . . ? C14 C15 C16 C11 -0.2(5) . . . . ? C12 C11 C16 C15 -0.5(4) . . . . ? N1 C11 C16 C15 178.9(3) . . . . ? O1 C1 C21 C22 26.2(4) . . . . ? N1 C1 C21 C22 -152.9(3) . . . . ? O1 C1 C21 C26 -153.7(3) . . . . ? N1 C1 C21 C26 27.2(4) . . . . ? C26 C21 C22 C23 -2.0(4) . . . . ? C1 C21 C22 C23 178.1(3) . . . . ? C21 C22 C23 N24 0.0(5) . . . . ? C22 C23 N24 C25 2.0(5) . . . . ? C23 N24 C25 C26 -1.9(4) . . . . ? N24 C25 C26 C21 -0.1(5) . . . . ? C22 C21 C26 C25 2.1(4) . . . . ? C1 C21 C26 C25 -178.0(3) . . . . ? loop_ _geom_hbond_atom_site_label_D _geom_hbond_atom_site_label_H _geom_hbond_atom_site_label_A _geom_hbond_distance_DH _geom_hbond_distance_HA _geom_hbond_distance_DA _geom_hbond_angle_DHA _geom_hbond_site_symmetry_A _geom_hbond_publ_flag # # Hydrogen bonding scheme # ======== ======= ====== # # D H A D-H H...A D...A D-H...A symm publ # - - - --- ----- ----- ------- ---- ---- # C23 H23 F13 0.95 2.60 3.222(4) 123 1_656 yes N1 H1 N24 0.88(4) 2.12(4) 2.991(4) 169(4) 4_444 yes C15 H15 O1 0.95 2.56 3.202(4) 125 4_454 yes C16 H16 O1 0.95 2.54 2.946(4) 106 . yes C25 H25 Cg1 0.95 2.65 3.484(3) 147 3_545 yes # C25 H25 C11 0.95 3.01 3.902(4) 157 3_545 no # C25 H25 C12 0.95 3.03 3.975(5) 172 3_545 no # C25 H25 C13 0.95 3.01 3.833(4) 145 3_545 no # C25 H25 C14 0.95 2.98 3.602(4) 125 3_545 no # C25 H25 C15 0.95 2.92 3.496(4) 120 3_545 no # C25 H25 C16 0.95 2.96 3.660(4) 132 3_545 no # Cg1 [C11,...,C16] is the C~6~ aromatic ring centroid located at 3_545 # Complete details for the C-H...\p(arene) interaction #========================================================================= data_NpoF_[9-09] _database_code_depnum_ccdc_archive 'CCDC 781754' #TrackingRef '- NxxF-Final04.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common NpoF _chemical_melting_point 412 _chemical_formula_moiety 'C12 H9 F N2 O' _chemical_formula_sum 'C12 H9 F N2 O' _chemical_formula_weight 216.21 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' F F 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Monoclinic _symmetry_space_group_name_H-M 'C c' _symmetry_space_group_name_Hall 'C -2yc' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' 'x, -y, z+1/2' 'x+1/2, y+1/2, z' 'x+1/2, -y+1/2, z+1/2' _cell_length_a 10.9275(5) _cell_length_b 12.8165(4) _cell_length_c 8.2422(4) _cell_angle_alpha 90.00 _cell_angle_beta 117.130(2) _cell_angle_gamma 90.00 _cell_volume 1027.33(8) _cell_formula_units_Z 4 _cell_measurement_temperature 150(2) _cell_measurement_reflns_used 3603 _cell_measurement_theta_min 2.55 _cell_measurement_theta_max 27.5 _exptl_crystal_description block _exptl_crystal_colour colourless _exptl_crystal_size_max 0.32 _exptl_crystal_size_mid 0.30 _exptl_crystal_size_min 0.26 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.398 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 448 _exptl_absorpt_coefficient_mu 0.104 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.968 _exptl_absorpt_correction_T_max 0.974 _exptl_absorpt_process_details '(SORTAV; Blessing, 1995)' _exptl_special_details ; ? ; _diffrn_ambient_temperature 150(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed X-ray tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device 'Nonius KappaCCD' _diffrn_measurement_method '\f, \w scans with \k offsets' _diffrn_standards_number ? _diffrn_standards_decay_% ? _diffrn_reflns_number 3196 _diffrn_reflns_av_R_equivalents 0.0410 _diffrn_reflns_av_sigmaI/netI 0.0395 _diffrn_reflns_limit_h_min -13 _diffrn_reflns_limit_h_max 14 _diffrn_reflns_limit_k_min -15 _diffrn_reflns_limit_k_max 16 _diffrn_reflns_limit_l_min -10 _diffrn_reflns_limit_l_max 10 _diffrn_reflns_theta_min 3.05 _diffrn_reflns_theta_max 27.48 _diffrn_measured_fraction_theta_max 0.986 _diffrn_reflns_theta_full 27.48 _diffrn_measured_fraction_theta_full 0.986 _reflns_number_total 1165 _reflns_number_gt 1013 _reflns_threshold_expression I>2\s(I) _computing_data_collection 'kappaCCD Server software (Nonius, 1997)' _computing_cell_refinement 'DENZO-SMN (Otwinowski and Minor, 1997)' _computing_data_reduction 'DENZO-SMN (Otwinowski and Minor, 1997)' _computing_structure_solution 'SHELXS97 (Sheldrick, 2008)' _computing_structure_refinement 'SHELXL97 (Sheldrick, 2008) and SORTX (McArdle, 1995)' _computing_molecular_graphics 'PLATON (Spek, 2009)' _computing_publication_material 'SHELXL97 and PREP8 (Ferguson, 1998)' _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 'w=1/[\s^2^(Fo^2^)+(0.0831P)^2^+0.5400P] 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_abs_structure_details '(Flack, 1983)' #_refine_ls_abs_structure_Flack 0(2) _refine_ls_number_reflns 1165 _refine_ls_number_parameters 154 _refine_ls_number_restraints 3 _refine_ls_R_factor_all 0.0616 _refine_ls_R_factor_gt 0.0506 _refine_ls_wR_factor_ref 0.1353 _refine_ls_wR_factor_gt 0.1237 _refine_ls_goodness_of_fit_ref 1.062 _refine_ls_restrained_S_all 1.063 _refine_ls_shift/su_max 0.000 _refine_ls_shift/su_mean 0.000 _refine_diff_density_max 0.223 _refine_diff_density_min -0.240 _refine_diff_density_rms 0.056 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 O1 O 0.5203(3) 0.08445(19) 0.5993(4) 0.0370(6) Uani 1 1 d . . . C1 C 0.4993(3) -0.0034(2) 0.5334(4) 0.0282(7) Uani 1 1 d . A . N1 N 0.3808(3) -0.0336(2) 0.3897(4) 0.0312(7) Uani 1 1 d . . . H1 H 0.363(5) -0.104(4) 0.368(7) 0.048(13) Uiso 1 1 d . . . C11 C 0.2648(3) 0.0335(3) 0.3011(4) 0.0291(7) Uani 1 1 d . A -1 C12 C 0.2736(4) 0.1298(3) 0.2328(5) 0.0322(8) Uani 1 1 d . A -1 H12 H 0.3604 0.1527 0.2463 0.039 Uiso 0.083(9) 1 calc PR B -1 C13 C 0.1606(4) 0.1944(3) 0.1452(5) 0.0372(8) Uani 1 1 d . A -1 H13 H 0.1702 0.2613 0.1026 0.045 Uiso 1 1 calc R A -1 C14 C 0.0326(4) 0.1594(3) 0.1209(5) 0.0392(9) Uani 1 1 d . A -1 H14 H -0.0463 0.2023 0.0602 0.047 Uiso 1 1 calc R A -1 C15 C 0.0207(4) 0.0624(3) 0.1852(6) 0.0402(9) Uani 1 1 d . A -1 H15 H -0.0668 0.0384 0.1673 0.048 Uiso 1 1 calc R A -1 C16 C 0.1359(3) -0.0003(3) 0.2757(5) 0.0338(8) Uani 1 1 d D A -1 H16 H 0.1268 -0.0666 0.3206 0.041 Uiso 0.917(9) 1 calc PR B -1 F12 F 0.3949(2) 0.16256(18) 0.2458(3) 0.0388(9) Uani 0.917(9) 1 d P B -2 F16 F 0.110(4) -0.0965(17) 0.301(5) 0.065(12) Uiso 0.083(9) 1 d PD B -2 C21 C 0.6051(3) -0.0884(3) 0.6129(5) 0.0281(7) Uani 1 1 d . . . C22 C 0.6999(4) -0.0839(3) 0.7960(5) 0.0323(8) Uani 1 1 d . A . H22 H 0.7027 -0.0251 0.8678 0.039 Uiso 1 1 calc R . . C23 C 0.7901(4) -0.1662(3) 0.8725(4) 0.0344(8) Uani 1 1 d . . . H23 H 0.8546 -0.1620 0.9978 0.041 Uiso 1 1 calc R A . N24 N 0.7913(3) -0.2511(2) 0.7797(4) 0.0333(7) Uani 1 1 d . A . C25 C 0.7039(4) -0.2530(3) 0.6016(5) 0.0329(8) Uani 1 1 d . . . H25 H 0.7065 -0.3114 0.5323 0.040 Uiso 1 1 calc R A . C26 C 0.6093(3) -0.1742(3) 0.5122(4) 0.0290(7) Uani 1 1 d . A . H26 H 0.5491 -0.1789 0.3853 0.035 Uiso 1 1 calc R . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 O1 0.0411(14) 0.0250(12) 0.0364(14) -0.0039(10) 0.0102(11) -0.0005(10) C1 0.0290(17) 0.0252(15) 0.0274(17) -0.0016(13) 0.0102(14) 0.0004(12) N1 0.0275(14) 0.0272(15) 0.0322(16) -0.0016(13) 0.0077(12) 0.0044(11) C11 0.0246(16) 0.0293(17) 0.0265(16) -0.0027(14) 0.0058(13) 0.0027(13) C12 0.0341(19) 0.0314(18) 0.0319(18) -0.0003(14) 0.0157(16) 0.0033(15) C13 0.045(2) 0.0357(18) 0.0326(18) 0.0062(16) 0.0186(16) 0.0100(16) C14 0.039(2) 0.040(2) 0.0354(18) 0.0010(16) 0.0139(17) 0.0136(16) C15 0.0283(18) 0.048(2) 0.039(2) -0.0052(17) 0.0099(16) 0.0021(16) C16 0.0295(17) 0.0315(17) 0.0350(19) -0.0034(15) 0.0100(15) -0.0004(14) F12 0.0363(14) 0.0354(13) 0.0482(15) 0.0073(11) 0.0224(11) 0.0030(10) C21 0.0228(15) 0.0271(16) 0.0320(18) -0.0007(13) 0.0102(13) -0.0020(12) C22 0.0298(17) 0.0335(18) 0.0281(17) -0.0030(14) 0.0084(14) -0.0025(13) C23 0.0304(17) 0.0391(19) 0.0241(17) 0.0006(15) 0.0040(13) -0.0002(15) N24 0.0286(14) 0.0310(14) 0.0348(15) 0.0047(13) 0.0096(12) 0.0033(12) C25 0.0311(18) 0.0283(16) 0.0359(18) -0.0011(14) 0.0123(15) 0.0026(13) C26 0.0260(16) 0.0287(17) 0.0279(16) -0.0002(13) 0.0086(13) 0.0018(13) _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 F12 C12 1.348(4) . ? F16 C16 1.303(19) . ? O1 C1 1.225(4) . ? C1 N1 1.353(4) . ? C1 C21 1.504(5) . ? N1 C11 1.427(4) . ? N1 H1 0.92(5) . ? C11 C12 1.378(5) . ? C11 C16 1.396(5) . ? C12 C13 1.385(5) . ? C12 H12 0.9500 . ? C13 C14 1.393(6) . ? C13 H13 0.9500 . ? C14 C15 1.381(6) . ? C14 H14 0.9500 . ? C15 C16 1.389(5) . ? C15 H15 0.9500 . ? C16 H16 0.9500 . ? C21 C22 1.388(5) . ? C21 C26 1.392(5) . ? C22 C23 1.384(5) . ? C22 H22 0.9500 . ? C23 N24 1.333(5) . ? C23 H23 0.9500 . ? N24 C25 1.338(5) . ? C25 C26 1.391(5) . ? C25 H25 0.9500 . ? C26 H26 0.9500 . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag O1 C1 N1 124.2(3) . . ? O1 C1 C21 121.4(3) . . ? N1 C1 C21 114.4(3) . . ? C1 N1 C11 123.2(3) . . ? C1 N1 H1 119(3) . . ? C11 N1 H1 115(3) . . ? C12 C11 C16 118.0(3) . . ? C12 C11 N1 122.6(3) . . ? C16 C11 N1 119.4(3) . . ? C11 C12 C13 122.5(3) . . ? C11 C12 H12 118.7 . . ? C13 C12 H12 118.7 . . ? C12 C13 C14 118.7(4) . . ? C12 C13 H13 120.7 . . ? C14 C13 H13 120.7 . . ? C15 C14 C13 119.9(4) . . ? C15 C14 H14 120.0 . . ? C13 C14 H14 120.0 . . ? C14 C15 C16 120.4(4) . . ? C14 C15 H15 119.8 . . ? C16 C15 H15 119.8 . . ? C15 C16 C11 120.4(3) . . ? C15 C16 H16 119.8 . . ? C11 C16 H16 119.8 . . ? C22 C21 C26 118.1(3) . . ? C22 C21 C1 119.2(3) . . ? C26 C21 C1 122.7(3) . . ? C23 C22 C21 119.1(3) . . ? C23 C22 H22 120.5 . . ? C21 C22 H22 120.5 . . ? N24 C23 C22 123.5(3) . . ? N24 C23 H23 118.2 . . ? C22 C23 H23 118.2 . . ? C23 N24 C25 117.1(3) . . ? N24 C25 C26 123.7(3) . . ? N24 C25 H25 118.2 . . ? C26 C25 H25 118.2 . . ? C25 C26 C21 118.4(3) . . ? C25 C26 H26 120.8 . . ? C21 C26 H26 120.8 . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag O1 C1 N1 C11 -1.7(5) . . . . ? C21 C1 N1 C11 176.5(3) . . . . ? C1 N1 C11 C12 54.5(5) . . . . ? C1 N1 C11 C16 -128.0(4) . . . . ? C16 C11 C12 C13 1.8(5) . . . . ? N1 C11 C12 C13 179.3(3) . . . . ? C11 C12 C13 C14 -1.8(5) . . . . ? C12 C13 C14 C15 0.6(5) . . . . ? C13 C14 C15 C16 0.7(6) . . . . ? C14 C15 C16 C11 -0.7(6) . . . . ? C12 C11 C16 C15 -0.5(5) . . . . ? N1 C11 C16 C15 -178.1(3) . . . . ? O1 C1 C21 C22 26.0(5) . . . . ? N1 C1 C21 C22 -152.3(3) . . . . ? O1 C1 C21 C26 -156.5(3) . . . . ? N1 C1 C21 C26 25.2(5) . . . . ? C26 C21 C22 C23 -2.7(5) . . . . ? C1 C21 C22 C23 174.9(3) . . . . ? C21 C22 C23 N24 -0.2(6) . . . . ? C22 C23 N24 C25 3.0(5) . . . . ? C23 N24 C25 C26 -3.0(5) . . . . ? N24 C25 C26 C21 0.1(5) . . . . ? C22 C21 C26 C25 2.8(5) . . . . ? C1 C21 C26 C25 -174.7(3) . . . . ? loop_ _geom_hbond_atom_site_label_D _geom_hbond_atom_site_label_H _geom_hbond_atom_site_label_A _geom_hbond_distance_DH _geom_hbond_distance_HA _geom_hbond_distance_DA _geom_hbond_angle_DHA _geom_hbond_site_symmetry_A _geom_hbond_publ_flag # # Hydrogen bonding scheme # ======== ======= ====== # # D H A D-H H...A D...A D-H...A symm publ # - - - --- ----- ----- ------- ---- ---- N1 H1 N24 0.92(5) 2.02(5) 2.930(4) 169(4) 4_444 yes C13 H13 O1 0.95 2.56 3.162(4) 122 4_454 yes C26 H26 O1 0.95 2.54 3.291(4) 136 2_554 yes C25 H25 Cg1 0.95 2.70 3.564(4) 151 3_545 yes # C25 H25 C11 0.95 3.02 3.946(5) 167 3_545 no # C25 H25 C12 0.95 2.97 3.767(5) 142 3_545 no # C25 H25 C13 0.95 3.00 3.634(5) 126 3_545 no # C25 H25 C14 0.95 3.06 3.701(5) 126 3_545 no # C25 H25 C15 0.95 3.10 3.889(5) 141 3_545 no # C25 H25 C16 0.95 3.07 3.999(5) 165 3_545 no # Cg1 [C11,...,C16] is the C~6~ aromatic ring centroids located # at site 3_545. # Complete details for the C-H...\p(arene) interaction #========================================================================= data_NmpF_[9-06] _database_code_depnum_ccdc_archive 'CCDC 781755' #TrackingRef '- NxxF-Final04.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common NmpF _chemical_melting_point 406 _chemical_formula_moiety 'C12 H9 F N2 O' _chemical_formula_sum 'C12 H9 F N2 O' _chemical_formula_weight 216.21 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' F F 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Triclinic _symmetry_space_group_name_H-M 'P -1' _symmetry_space_group_name_Hall '-P 1' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 9.7585(3) _cell_length_b 9.7644(2) _cell_length_c 21.1700(6) _cell_angle_alpha 96.1397(17) _cell_angle_beta 95.7365(14) _cell_angle_gamma 89.9958(18) _cell_volume 1995.47(9) _cell_formula_units_Z 8 _cell_measurement_temperature 150(2) _cell_measurement_reflns_used 20462 _cell_measurement_theta_min 2.55 _cell_measurement_theta_max 27.5 _exptl_crystal_description block _exptl_crystal_colour colourless _exptl_crystal_size_max 0.32 _exptl_crystal_size_mid 0.26 _exptl_crystal_size_min 0.18 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.439 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 896 _exptl_absorpt_coefficient_mu 0.107 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.9666 _exptl_absorpt_correction_T_max 0.9810 _exptl_absorpt_process_details '(SORTAV; Blessing, 1995)' _exptl_special_details ; ? ; _diffrn_ambient_temperature 150(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed X-ray tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device 'Nonius KappaCCD' _diffrn_measurement_method '\f, \w scans with \k offsets' _diffrn_standards_number 22261 _diffrn_standards_decay_% ? _diffrn_reflns_number 22261 _diffrn_reflns_av_R_equivalents 0.0491 _diffrn_reflns_av_sigmaI/netI 0.0522 _diffrn_reflns_limit_h_min -12 _diffrn_reflns_limit_h_max 12 _diffrn_reflns_limit_k_min -12 _diffrn_reflns_limit_k_max 12 _diffrn_reflns_limit_l_min -21 _diffrn_reflns_limit_l_max 27 _diffrn_reflns_theta_min 2.70 _diffrn_reflns_theta_max 27.45 _diffrn_measured_fraction_theta_max 0.985 _diffrn_reflns_theta_full 27.45 _diffrn_measured_fraction_theta_full 0.985 _reflns_number_total 8999 _reflns_number_gt 6611 _reflns_threshold_expression I>2\s(I) _computing_data_collection 'kappaCCD Server software (Nonius, 1997)' _computing_cell_refinement 'DENZO-SMN (Otwinowski and Minor, 1997)' _computing_data_reduction 'DENZO-SMN (Otwinowski and Minor, 1997)' _computing_structure_solution 'SHELXS97 (Sheldrick, 2008)' _computing_structure_refinement 'SHELXL97 (Sheldrick, 2008) and SORTX (McArdle, 1995)' _computing_molecular_graphics 'PLATON (Spek, 2003)' _computing_publication_material 'SHELXL97 and PREP8 (Ferguson, 1998)' _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 'w=1/[\s^2^(Fo^2^)+(0.0504P)^2^+0.5837P] 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 8999 _refine_ls_number_parameters 593 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0760 _refine_ls_R_factor_gt 0.0504 _refine_ls_wR_factor_ref 0.1242 _refine_ls_wR_factor_gt 0.1105 _refine_ls_goodness_of_fit_ref 1.039 _refine_ls_restrained_S_all 1.039 _refine_ls_shift/su_max 0.001 _refine_ls_shift/su_mean 0.000 _refine_diff_density_max 0.228 _refine_diff_density_min -0.240 _refine_diff_density_rms 0.044 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 F14A F 0.72494(11) 1.35857(10) 0.13880(5) 0.0484(3) Uani 1 1 d . . . O1A O 0.26496(13) 0.88372(12) 0.04524(5) 0.0397(3) Uani 1 1 d . . . C1A C 0.24980(16) 0.88255(15) 0.10189(8) 0.0295(3) Uani 1 1 d . . . N1A N 0.32257(14) 0.96479(13) 0.14954(7) 0.0288(3) Uani 1 1 d . . . H1A H 0.3047(18) 0.9641(17) 0.1882(9) 0.033(5) Uiso 1 1 d . . . C11A C 0.42518(16) 1.06372(15) 0.14309(8) 0.0284(3) Uani 1 1 d . . . C12A C 0.47254(18) 1.08748(17) 0.08530(8) 0.0369(4) Uani 1 1 d . . . H12A H 0.4353 1.0362 0.0467 0.044 Uiso 1 1 calc R . . C13A C 0.57456(19) 1.18652(18) 0.08419(9) 0.0398(4) Uani 1 1 d . . . H13A H 0.6082 1.2030 0.0451 0.048 Uiso 1 1 calc R . . C14A C 0.62572(17) 1.26000(16) 0.14041(9) 0.0351(4) Uani 1 1 d . . . C15A C 0.58084(18) 1.23984(16) 0.19791(8) 0.0355(4) Uani 1 1 d . . . H15A H 0.6179 1.2926 0.2361 0.043 Uiso 1 1 calc R . . C16A C 0.48003(17) 1.14069(16) 0.19910(8) 0.0326(4) Uani 1 1 d . . . H16A H 0.4478 1.1249 0.2386 0.039 Uiso 1 1 calc R . . C21A C 0.14677(16) 0.78456(15) 0.12159(7) 0.0278(3) Uani 1 1 d . . . C22A C 0.12383(16) 0.76990(16) 0.18406(8) 0.0304(3) Uani 1 1 d . . . H22A H 0.1756 0.8269 0.2172 0.036 Uiso 1 1 calc R . . N23A N 0.03326(14) 0.68037(13) 0.20078(7) 0.0328(3) Uani 1 1 d . . . C24A C -0.04023(17) 0.60250(16) 0.15322(8) 0.0345(4) Uani 1 1 d . . . H24A H -0.1054 0.5389 0.1640 0.041 Uiso 1 1 calc R . . C25A C -0.02626(19) 0.60987(17) 0.08949(8) 0.0389(4) Uani 1 1 d . . . H25A H -0.0813 0.5537 0.0572 0.047 Uiso 1 1 calc R . . C26A C 0.06989(18) 0.70102(16) 0.07371(8) 0.0343(4) Uani 1 1 d . . . H26A H 0.0833 0.7065 0.0302 0.041 Uiso 1 1 calc R . . F14B F -0.15464(11) -0.02453(10) 0.13809(5) 0.0493(3) Uani 1 1 d . . . O1B O 0.25987(13) 0.41131(12) 0.04300(6) 0.0426(3) Uani 1 1 d . . . C1B C 0.30068(17) 0.43746(16) 0.09957(8) 0.0315(4) Uani 1 1 d . . . N1B N 0.25051(14) 0.37546(13) 0.14709(7) 0.0305(3) Uani 1 1 d . . . H1B H 0.2840(19) 0.3962(18) 0.1843(9) 0.037(5) Uiso 1 1 d . . . C11B C 0.14610(16) 0.27282(15) 0.14134(8) 0.0298(3) Uani 1 1 d . . . C12B C 0.08020(18) 0.21453(18) 0.08318(9) 0.0382(4) Uani 1 1 d . . . H12B H 0.1051 0.2425 0.0442 0.046 Uiso 1 1 calc R . . C13B C -0.02241(19) 0.11498(18) 0.08258(9) 0.0411(4) Uani 1 1 d . . . H13B H -0.0691 0.0755 0.0433 0.049 Uiso 1 1 calc R . . C14B C -0.05512(17) 0.07474(16) 0.13929(9) 0.0366(4) Uani 1 1 d . . . C15B C 0.00898(18) 0.12874(17) 0.19722(9) 0.0367(4) Uani 1 1 d . . . H15B H -0.0153 0.0985 0.2358 0.044 Uiso 1 1 calc R . . C16B C 0.10998(17) 0.22859(16) 0.19783(8) 0.0338(4) Uani 1 1 d . . . H16B H 0.1554 0.2675 0.2375 0.041 Uiso 1 1 calc R . . C21B C 0.41187(16) 0.54542(15) 0.11968(7) 0.0290(3) Uani 1 1 d . . . C22B C 0.46238(17) 0.58706(16) 0.18220(8) 0.0321(4) Uani 1 1 d . . . H22B H 0.4260 0.5436 0.2151 0.038 Uiso 1 1 calc R . . N23B N 0.55942(15) 0.68490(14) 0.19937(7) 0.0349(3) Uani 1 1 d . . . C24B C 0.61127(18) 0.74270(17) 0.15213(8) 0.0350(4) Uani 1 1 d . . . H24B H 0.6807 0.8117 0.1632 0.042 Uiso 1 1 calc R . . C25B C 0.56912(19) 0.70731(18) 0.08833(9) 0.0398(4) Uani 1 1 d . . . H25B H 0.6098 0.7498 0.0563 0.048 Uiso 1 1 calc R . . C26B C 0.46639(18) 0.60870(16) 0.07197(8) 0.0357(4) Uani 1 1 d . . . H26B H 0.4334 0.5845 0.0285 0.043 Uiso 1 1 calc R . . F14C F -0.35744(11) 1.16272(10) 0.36165(5) 0.0485(3) Uani 1 1 d . . . O1C O 0.11705(13) 0.74517(12) 0.45458(5) 0.0392(3) Uani 1 1 d . . . C1C C 0.11886(16) 0.70395(15) 0.39787(8) 0.0294(3) Uani 1 1 d . . . N1C N 0.03665(14) 0.75517(13) 0.35043(7) 0.0293(3) Uani 1 1 d . . . H1C H 0.0422(18) 0.7192(17) 0.3116(9) 0.034(5) Uiso 1 1 d . . . C11C C -0.06253(16) 0.86037(15) 0.35682(8) 0.0283(3) Uani 1 1 d . . . C12C C -0.08649(18) 0.93426(17) 0.41468(8) 0.0367(4) Uani 1 1 d . . . H12C H -0.0353 0.9147 0.4532 0.044 Uiso 1 1 calc R . . C13C C -0.18547(19) 1.03669(18) 0.41587(9) 0.0400(4) Uani 1 1 d . . . H13C H -0.2022 1.0879 0.4550 0.048 Uiso 1 1 calc R . . C14C C -0.25855(17) 1.06272(16) 0.35989(9) 0.0357(4) Uani 1 1 d . . . C15C C -0.23798(18) 0.99209(17) 0.30220(8) 0.0358(4) Uani 1 1 d . . . H15C H -0.2903 1.0121 0.2641 0.043 Uiso 1 1 calc R . . C16C C -0.13869(17) 0.89064(16) 0.30104(8) 0.0319(4) Uani 1 1 d . . . H16C H -0.1224 0.8409 0.2615 0.038 Uiso 1 1 calc R . . C21C C 0.21702(16) 0.59220(15) 0.37835(7) 0.0279(3) Uani 1 1 d . . . C22C C 0.23203(17) 0.54077(15) 0.31594(8) 0.0306(3) Uani 1 1 d . . . H22C H 0.1750 0.5771 0.2828 0.037 Uiso 1 1 calc R . . N23C N 0.32229(14) 0.44251(13) 0.29925(6) 0.0329(3) Uani 1 1 d . . . C24C C 0.39976(18) 0.39076(16) 0.34702(8) 0.0346(4) Uani 1 1 d . . . H24C H 0.4639 0.3209 0.3364 0.041 Uiso 1 1 calc R . . C25C C 0.39104(19) 0.43375(18) 0.41064(9) 0.0391(4) Uani 1 1 d . . . H25C H 0.4465 0.3932 0.4430 0.047 Uiso 1 1 calc R . . C26C C 0.29978(18) 0.53728(17) 0.42643(8) 0.0347(4) Uani 1 1 d . . . H26C H 0.2938 0.5706 0.4699 0.042 Uiso 1 1 calc R . . F14D F 1.02575(11) 0.28365(10) 0.36167(5) 0.0488(3) Uani 1 1 d . . . O1D O 0.58938(13) 0.74188(13) 0.45714(6) 0.0429(3) Uani 1 1 d . . . C1D C 0.56323(17) 0.75655(16) 0.40050(8) 0.0312(4) Uani 1 1 d . . . N1D N 0.62556(14) 0.68436(13) 0.35310(7) 0.0300(3) Uani 1 1 d . . . H1D H 0.6048(19) 0.7004(17) 0.3158(9) 0.033(5) Uiso 1 1 d . . . C11D C 0.72831(16) 0.58285(15) 0.35877(8) 0.0300(3) Uani 1 1 d . . . C12D C 0.78598(19) 0.54264(17) 0.41674(9) 0.0380(4) Uani 1 1 d . . . H12D H 0.7574 0.5849 0.4557 0.046 Uiso 1 1 calc R . . C13D C 0.88523(19) 0.44072(18) 0.41746(9) 0.0410(4) Uani 1 1 d . . . H13D H 0.9240 0.4117 0.4567 0.049 Uiso 1 1 calc R . . C14D C 0.92648(17) 0.38267(16) 0.36077(9) 0.0364(4) Uani 1 1 d . . . C15D C 0.87302(17) 0.42098(17) 0.30282(9) 0.0360(4) Uani 1 1 d . . . H15D H 0.9040 0.3796 0.2642 0.043 Uiso 1 1 calc R . . C16D C 0.77306(17) 0.52133(16) 0.30216(8) 0.0333(4) Uani 1 1 d . . . H16D H 0.7344 0.5487 0.2625 0.040 Uiso 1 1 calc R . . C21D C 0.45562(16) 0.85842(15) 0.38037(7) 0.0287(3) Uani 1 1 d . . . C22D C 0.41488(17) 0.88027(16) 0.31766(8) 0.0318(4) Uani 1 1 d . . . H22D H 0.4587 0.8287 0.2849 0.038 Uiso 1 1 calc R . . N23D N 0.31725(14) 0.96979(13) 0.30032(7) 0.0335(3) Uani 1 1 d . . . C24D C 0.25904(18) 1.04326(17) 0.34748(8) 0.0354(4) Uani 1 1 d . . . H24D H 0.1906 1.1081 0.3364 0.042 Uiso 1 1 calc R . . C25D C 0.29326(19) 1.02980(18) 0.41137(9) 0.0395(4) Uani 1 1 d . . . H25D H 0.2500 1.0847 0.4433 0.047 Uiso 1 1 calc R . . C26D C 0.39176(18) 0.93489(17) 0.42779(8) 0.0354(4) Uani 1 1 d . . . H26D H 0.4156 0.9221 0.4714 0.042 Uiso 1 1 calc R . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 F14A 0.0444(6) 0.0442(6) 0.0576(7) 0.0060(5) 0.0087(5) -0.0163(5) O1A 0.0437(7) 0.0495(7) 0.0256(7) 0.0030(5) 0.0036(5) -0.0094(6) C1A 0.0293(8) 0.0322(8) 0.0269(9) 0.0034(6) 0.0015(7) 0.0024(6) N1A 0.0320(7) 0.0313(7) 0.0231(7) 0.0026(5) 0.0033(6) -0.0030(5) C11A 0.0265(8) 0.0285(8) 0.0303(9) 0.0044(6) 0.0026(7) 0.0021(6) C12A 0.0425(10) 0.0372(9) 0.0308(9) 0.0005(7) 0.0071(8) -0.0060(7) C13A 0.0431(10) 0.0416(9) 0.0371(10) 0.0061(7) 0.0129(8) -0.0060(8) C14A 0.0298(9) 0.0315(8) 0.0449(11) 0.0065(7) 0.0052(7) -0.0034(7) C15A 0.0359(9) 0.0341(8) 0.0353(10) 0.0026(7) -0.0019(7) -0.0039(7) C16A 0.0331(9) 0.0355(8) 0.0296(9) 0.0057(7) 0.0023(7) -0.0007(7) C21A 0.0266(8) 0.0286(8) 0.0277(8) 0.0028(6) 0.0003(6) 0.0036(6) C22A 0.0310(9) 0.0327(8) 0.0265(9) 0.0007(6) 0.0004(7) -0.0026(6) N23A 0.0338(8) 0.0336(7) 0.0312(8) 0.0052(6) 0.0022(6) -0.0030(6) C24A 0.0331(9) 0.0326(8) 0.0373(10) 0.0050(7) 0.0002(7) -0.0038(7) C25A 0.0416(10) 0.0396(9) 0.0328(10) 0.0006(7) -0.0056(8) -0.0073(8) C26A 0.0400(10) 0.0373(9) 0.0249(9) 0.0034(7) -0.0001(7) -0.0022(7) F14B 0.0424(6) 0.0451(6) 0.0601(7) 0.0075(5) 0.0021(5) -0.0149(5) O1B 0.0504(8) 0.0495(7) 0.0270(7) 0.0044(5) -0.0006(6) -0.0111(6) C1B 0.0333(9) 0.0322(8) 0.0292(9) 0.0039(6) 0.0030(7) 0.0029(7) N1B 0.0330(8) 0.0327(7) 0.0252(8) 0.0037(6) -0.0007(6) -0.0027(6) C11B 0.0274(8) 0.0278(8) 0.0341(9) 0.0049(6) 0.0016(7) 0.0023(6) C12B 0.0386(10) 0.0434(9) 0.0322(10) 0.0080(7) -0.0034(8) -0.0049(8) C13B 0.0401(10) 0.0430(10) 0.0379(10) 0.0046(8) -0.0069(8) -0.0074(8) C14B 0.0312(9) 0.0305(8) 0.0481(11) 0.0061(7) 0.0024(8) -0.0038(7) C15B 0.0389(10) 0.0357(9) 0.0372(10) 0.0069(7) 0.0092(8) -0.0007(7) C16B 0.0360(9) 0.0345(8) 0.0302(9) 0.0016(7) 0.0026(7) 0.0004(7) C21B 0.0305(8) 0.0288(8) 0.0281(9) 0.0037(6) 0.0038(7) 0.0036(6) C22B 0.0328(9) 0.0337(8) 0.0307(9) 0.0064(6) 0.0048(7) -0.0014(7) N23B 0.0366(8) 0.0350(7) 0.0331(8) 0.0041(6) 0.0031(6) -0.0022(6) C24B 0.0336(9) 0.0331(8) 0.0389(10) 0.0054(7) 0.0054(7) -0.0023(7) C25B 0.0459(11) 0.0403(9) 0.0353(10) 0.0087(7) 0.0099(8) -0.0046(8) C26B 0.0419(10) 0.0373(9) 0.0279(9) 0.0033(7) 0.0043(7) 0.0003(7) F14C 0.0443(6) 0.0430(6) 0.0576(7) 0.0031(5) 0.0047(5) 0.0164(5) O1C 0.0494(8) 0.0429(7) 0.0242(6) 0.0014(5) 0.0013(5) 0.0084(5) C1C 0.0310(8) 0.0311(8) 0.0261(9) 0.0046(6) 0.0006(7) -0.0030(6) N1C 0.0317(7) 0.0317(7) 0.0240(8) 0.0023(5) 0.0019(6) 0.0015(6) C11C 0.0273(8) 0.0254(7) 0.0322(9) 0.0031(6) 0.0028(7) -0.0017(6) C12C 0.0364(9) 0.0405(9) 0.0311(9) -0.0017(7) -0.0020(7) 0.0039(7) C13C 0.0402(10) 0.0401(9) 0.0375(10) -0.0047(7) 0.0033(8) 0.0047(8) C14C 0.0308(9) 0.0299(8) 0.0467(11) 0.0048(7) 0.0050(8) 0.0037(7) C15C 0.0350(9) 0.0379(9) 0.0351(10) 0.0102(7) 0.0003(7) 0.0024(7) C16C 0.0344(9) 0.0345(8) 0.0271(9) 0.0038(6) 0.0045(7) 0.0012(7) C21C 0.0281(8) 0.0280(7) 0.0278(8) 0.0054(6) 0.0009(6) -0.0030(6) C22C 0.0320(9) 0.0319(8) 0.0278(9) 0.0058(6) -0.0004(7) 0.0027(7) N23C 0.0344(8) 0.0350(7) 0.0297(8) 0.0052(6) 0.0031(6) 0.0038(6) C24C 0.0343(9) 0.0338(8) 0.0366(10) 0.0078(7) 0.0042(7) 0.0036(7) C25C 0.0399(10) 0.0445(10) 0.0336(10) 0.0112(7) -0.0008(8) 0.0066(8) C26C 0.0385(10) 0.0402(9) 0.0253(9) 0.0054(7) 0.0013(7) 0.0019(7) F14D 0.0452(6) 0.0438(6) 0.0585(7) 0.0102(5) 0.0065(5) 0.0147(5) O1D 0.0501(8) 0.0522(7) 0.0271(7) 0.0078(5) 0.0034(6) 0.0102(6) C1D 0.0322(9) 0.0331(8) 0.0284(9) 0.0045(6) 0.0030(7) -0.0038(7) N1D 0.0329(8) 0.0329(7) 0.0246(8) 0.0058(6) 0.0024(6) 0.0020(6) C11D 0.0281(8) 0.0294(8) 0.0331(9) 0.0055(6) 0.0037(7) -0.0018(6) C12D 0.0423(10) 0.0411(9) 0.0323(10) 0.0094(7) 0.0067(8) 0.0054(8) C13D 0.0427(10) 0.0445(10) 0.0373(10) 0.0141(8) 0.0017(8) 0.0071(8) C14D 0.0316(9) 0.0309(8) 0.0472(11) 0.0070(7) 0.0034(8) 0.0015(7) C15D 0.0341(9) 0.0360(9) 0.0376(10) 0.0000(7) 0.0058(8) 0.0009(7) C16D 0.0331(9) 0.0358(8) 0.0302(9) 0.0032(7) -0.0002(7) -0.0013(7) C21D 0.0286(8) 0.0295(8) 0.0277(9) 0.0018(6) 0.0027(7) -0.0056(6) C22D 0.0334(9) 0.0342(8) 0.0277(9) 0.0020(6) 0.0042(7) 0.0006(7) N23D 0.0348(8) 0.0336(7) 0.0321(8) 0.0040(6) 0.0025(6) 0.0011(6) C24D 0.0359(9) 0.0327(8) 0.0373(10) 0.0019(7) 0.0041(8) 0.0021(7) C25D 0.0426(10) 0.0415(9) 0.0336(10) -0.0032(7) 0.0076(8) 0.0049(8) C26D 0.0369(9) 0.0418(9) 0.0268(9) 0.0010(7) 0.0025(7) -0.0006(7) _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 F14A C14A 1.3707(18) . ? O1A C1A 1.2241(19) . ? C1A N1A 1.360(2) . ? C1A C21A 1.507(2) . ? N1A C11A 1.418(2) . ? N1A H1A 0.854(19) . ? C11A C12A 1.392(2) . ? C11A C16A 1.393(2) . ? C12A C13A 1.392(2) . ? C12A H12A 0.9500 . ? C13A C14A 1.371(2) . ? C13A H13A 0.9500 . ? C14A C15A 1.368(2) . ? C15A C16A 1.384(2) . ? C15A H15A 0.9500 . ? C16A H16A 0.9500 . ? C21A C22A 1.385(2) . ? C21A C26A 1.388(2) . ? C22A N23A 1.341(2) . ? C22A H22A 0.9500 . ? N23A C24A 1.341(2) . ? C24A C25A 1.379(2) . ? C24A H24A 0.9500 . ? C25A C26A 1.382(2) . ? C25A H25A 0.9500 . ? C26A H26A 0.9500 . ? F14B C14B 1.3687(18) . ? O1B C1B 1.2237(19) . ? C1B N1B 1.359(2) . ? C1B C21B 1.511(2) . ? N1B C11B 1.417(2) . ? N1B H1B 0.827(19) . ? C11B C16B 1.391(2) . ? C11B C12B 1.395(2) . ? C12B C13B 1.394(2) . ? C12B H12B 0.9500 . ? C13B C14B 1.369(3) . ? C13B H13B 0.9500 . ? C14B C15B 1.372(2) . ? C15B C16B 1.385(2) . ? C15B H15B 0.9500 . ? C16B H16B 0.9500 . ? C21B C22B 1.384(2) . ? C21B C26B 1.388(2) . ? C22B N23B 1.341(2) . ? C22B H22B 0.9500 . ? N23B C24B 1.341(2) . ? C24B C25B 1.379(2) . ? C24B H24B 0.9500 . ? C25B C26B 1.383(2) . ? C25B H25B 0.9500 . ? C26B H26B 0.9500 . ? F14C C14C 1.3731(19) . ? O1C C1C 1.2266(19) . ? C1C N1C 1.360(2) . ? C1C C21C 1.504(2) . ? N1C C11C 1.416(2) . ? N1C H1C 0.865(18) . ? C11C C16C 1.390(2) . ? C11C C12C 1.394(2) . ? C12C C13C 1.390(2) . ? C12C H12C 0.9500 . ? C13C C14C 1.369(3) . ? C13C H13C 0.9500 . ? C14C C15C 1.370(2) . ? C15C C16C 1.386(2) . ? C15C H15C 0.9500 . ? C16C H16C 0.9500 . ? C21C C22C 1.384(2) . ? C21C C26C 1.389(2) . ? C22C N23C 1.346(2) . ? C22C H22C 0.9500 . ? N23C C24C 1.344(2) . ? C24C C25C 1.378(2) . ? C24C H24C 0.9500 . ? C25C C26C 1.383(2) . ? C25C H25C 0.9500 . ? C26C H26C 0.9500 . ? F14D C14D 1.3688(19) . ? O1D C1D 1.2244(19) . ? C1D N1D 1.358(2) . ? C1D C21D 1.508(2) . ? N1D C11D 1.415(2) . ? N1D H1D 0.826(19) . ? C11D C16D 1.392(2) . ? C11D C12D 1.393(2) . ? C12D C13D 1.389(2) . ? C12D H12D 0.9500 . ? C13D C14D 1.369(3) . ? C13D H13D 0.9500 . ? C14D C15D 1.374(2) . ? C15D C16D 1.383(2) . ? C15D H15D 0.9500 . ? C16D H16D 0.9500 . ? C21D C26D 1.385(2) . ? C21D C22D 1.386(2) . ? C22D N23D 1.344(2) . ? C22D H22D 0.9500 . ? N23D C24D 1.339(2) . ? C24D C25D 1.381(2) . ? C24D H24D 0.9500 . ? C25D C26D 1.380(2) . ? C25D H25D 0.9500 . ? C26D H26D 0.9500 . ? 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 O1A C1A N1A 123.68(15) . . ? O1A C1A C21A 119.56(14) . . ? N1A C1A C21A 116.75(14) . . ? C1A N1A C11A 127.18(14) . . ? C1A N1A H1A 120.3(12) . . ? C11A N1A H1A 112.4(11) . . ? C12A C11A C16A 119.31(15) . . ? C12A C11A N1A 124.32(14) . . ? C16A C11A N1A 116.37(14) . . ? C13A C12A C11A 119.82(16) . . ? C13A C12A H12A 120.1 . . ? C11A C12A H12A 120.1 . . ? C14A C13A C12A 118.98(16) . . ? C14A C13A H13A 120.5 . . ? C12A C13A H13A 120.5 . . ? C15A C14A F14A 118.71(15) . . ? C15A C14A C13A 122.67(15) . . ? F14A C14A C13A 118.62(16) . . ? C14A C15A C16A 118.36(16) . . ? C14A C15A H15A 120.8 . . ? C16A C15A H15A 120.8 . . ? C15A C16A C11A 120.85(16) . . ? C15A C16A H16A 119.6 . . ? C11A C16A H16A 119.6 . . ? C22A C21A C26A 117.21(14) . . ? C22A C21A C1A 125.02(14) . . ? C26A C21A C1A 117.76(14) . . ? N23A C22A C21A 124.21(14) . . ? N23A C22A H22A 117.9 . . ? C21A C22A H22A 117.9 . . ? C24A N23A C22A 116.88(14) . . ? N23A C24A C25A 123.51(15) . . ? N23A C24A H24A 118.2 . . ? C25A C24A H24A 118.2 . . ? C24A C25A C26A 118.34(15) . . ? C24A C25A H25A 120.8 . . ? C26A C25A H25A 120.8 . . ? C25A C26A C21A 119.82(16) . . ? C25A C26A H26A 120.1 . . ? C21A C26A H26A 120.1 . . ? O1B C1B N1B 123.74(15) . . ? O1B C1B C21B 119.77(15) . . ? N1B C1B C21B 116.49(14) . . ? C1B N1B C11B 127.79(15) . . ? C1B N1B H1B 119.1(13) . . ? C11B N1B H1B 113.1(13) . . ? C16B C11B C12B 119.33(15) . . ? C16B C11B N1B 116.73(14) . . ? C12B C11B N1B 123.94(15) . . ? C13B C12B C11B 119.60(16) . . ? C13B C12B H12B 120.2 . . ? C11B C12B H12B 120.2 . . ? C14B C13B C12B 119.17(16) . . ? C14B C13B H13B 120.4 . . ? C12B C13B H13B 120.4 . . ? F14B C14B C13B 118.69(15) . . ? F14B C14B C15B 118.66(16) . . ? C13B C14B C15B 122.64(16) . . ? C14B C15B C16B 118.16(16) . . ? C14B C15B H15B 120.9 . . ? C16B C15B H15B 120.9 . . ? C15B C16B C11B 121.07(16) . . ? C15B C16B H16B 119.5 . . ? C11B C16B H16B 119.5 . . ? C22B C21B C26B 117.53(15) . . ? C22B C21B C1B 124.86(14) . . ? C26B C21B C1B 117.61(14) . . ? N23B C22B C21B 124.17(15) . . ? N23B C22B H22B 117.9 . . ? C21B C22B H22B 117.9 . . ? C24B N23B C22B 116.83(15) . . ? N23B C24B C25B 123.46(16) . . ? N23B C24B H24B 118.3 . . ? C25B C24B H24B 118.3 . . ? C24B C25B C26B 118.56(16) . . ? C24B C25B H25B 120.7 . . ? C26B C25B H25B 120.7 . . ? C25B C26B C21B 119.42(16) . . ? C25B C26B H26B 120.3 . . ? C21B C26B H26B 120.3 . . ? O1C C1C N1C 123.34(15) . . ? O1C C1C C21C 119.55(14) . . ? N1C C1C C21C 117.10(14) . . ? C1C N1C C11C 127.45(14) . . ? C1C N1C H1C 118.0(12) . . ? C11C N1C H1C 114.5(12) . . ? C16C C11C C12C 119.13(15) . . ? C16C C11C N1C 116.69(14) . . ? C12C C11C N1C 124.18(15) . . ? C13C C12C C11C 119.82(16) . . ? C13C C12C H12C 120.1 . . ? C11C C12C H12C 120.1 . . ? C14C C13C C12C 119.15(16) . . ? C14C C13C H13C 120.4 . . ? C12C C13C H13C 120.4 . . ? C13C C14C C15C 122.65(16) . . ? C13C C14C F14C 118.74(16) . . ? C15C C14C F14C 118.61(16) . . ? C14C C15C C16C 118.13(16) . . ? C14C C15C H15C 120.9 . . ? C16C C15C H15C 120.9 . . ? C15C C16C C11C 121.12(15) . . ? C15C C16C H16C 119.4 . . ? C11C C16C H16C 119.4 . . ? C22C C21C C26C 117.47(15) . . ? C22C C21C C1C 124.87(14) . . ? C26C C21C C1C 117.66(14) . . ? N23C C22C C21C 124.10(15) . . ? N23C C22C H22C 117.9 . . ? C21C C22C H22C 117.9 . . ? C24C N23C C22C 116.82(14) . . ? N23C C24C C25C 123.41(16) . . ? N23C C24C H24C 118.3 . . ? C25C C24C H24C 118.3 . . ? C24C C25C C26C 118.59(16) . . ? C24C C25C H25C 120.7 . . ? C26C C25C H25C 120.7 . . ? C25C C26C C21C 119.58(16) . . ? C25C C26C H26C 120.2 . . ? C21C C26C H26C 120.2 . . ? O1D C1D N1D 123.56(15) . . ? O1D C1D C21D 119.84(15) . . ? N1D C1D C21D 116.60(14) . . ? C1D N1D C11D 128.02(14) . . ? C1D N1D H1D 119.0(13) . . ? C11D N1D H1D 113.0(13) . . ? C16D C11D C12D 119.21(15) . . ? C16D C11D N1D 116.68(14) . . ? C12D C11D N1D 124.11(15) . . ? C13D C12D C11D 119.95(17) . . ? C13D C12D H12D 120.0 . . ? C11D C12D H12D 120.0 . . ? C14D C13D C12D 119.08(16) . . ? C14D C13D H13D 120.5 . . ? C12D C13D H13D 120.5 . . ? F14D C14D C13D 118.96(16) . . ? F14D C14D C15D 118.53(16) . . ? C13D C14D C15D 122.50(16) . . ? C14D C15D C16D 118.33(16) . . ? C14D C15D H15D 120.8 . . ? C16D C15D H15D 120.8 . . ? C15D C16D C11D 120.92(16) . . ? C15D C16D H16D 119.5 . . ? C11D C16D H16D 119.5 . . ? C26D C21D C22D 117.46(15) . . ? C26D C21D C1D 117.84(14) . . ? C22D C21D C1D 124.70(15) . . ? N23D C22D C21D 124.10(15) . . ? N23D C22D H22D 117.9 . . ? C21D C22D H22D 117.9 . . ? C24D N23D C22D 116.78(14) . . ? N23D C24D C25D 123.48(16) . . ? N23D C24D H24D 118.3 . . ? C25D C24D H24D 118.3 . . ? C26D C25D C24D 118.53(16) . . ? C26D C25D H25D 120.7 . . ? C24D C25D H25D 120.7 . . ? C25D C26D C21D 119.62(16) . . ? C25D C26D H26D 120.2 . . ? C21D C26D H26D 120.2 . . ? 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 O1A C1A N1A C11A 0.2(3) . . . . ? C21A C1A N1A C11A 179.49(14) . . . . ? C1A N1A C11A C12A -3.2(3) . . . . ? C1A N1A C11A C16A 176.70(15) . . . . ? C16A C11A C12A C13A 0.6(3) . . . . ? N1A C11A C12A C13A -179.53(15) . . . . ? C11A C12A C13A C14A -0.6(3) . . . . ? C12A C13A C14A C15A 0.2(3) . . . . ? C12A C13A C14A F14A -179.18(15) . . . . ? F14A C14A C15A C16A 179.61(14) . . . . ? C13A C14A C15A C16A 0.3(3) . . . . ? C14A C15A C16A C11A -0.3(2) . . . . ? C12A C11A C16A C15A -0.1(2) . . . . ? N1A C11A C16A C15A 179.96(14) . . . . ? O1A C1A C21A C22A 177.51(15) . . . . ? N1A C1A C21A C22A -1.8(2) . . . . ? O1A C1A C21A C26A -1.6(2) . . . . ? N1A C1A C21A C26A 179.09(14) . . . . ? C26A C21A C22A N23A 0.3(2) . . . . ? C1A C21A C22A N23A -178.80(14) . . . . ? C21A C22A N23A C24A -1.1(2) . . . . ? C22A N23A C24A C25A 0.4(2) . . . . ? N23A C24A C25A C26A 0.9(3) . . . . ? C24A C25A C26A C21A -1.6(3) . . . . ? C22A C21A C26A C25A 1.1(2) . . . . ? C1A C21A C26A C25A -179.76(15) . . . . ? O1B C1B N1B C11B 0.1(3) . . . . ? C21B C1B N1B C11B 179.36(14) . . . . ? C1B N1B C11B C16B -178.08(15) . . . . ? C1B N1B C11B C12B 2.5(3) . . . . ? C16B C11B C12B C13B 1.2(3) . . . . ? N1B C11B C12B C13B -179.37(15) . . . . ? C11B C12B C13B C14B -1.0(3) . . . . ? C12B C13B C14B F14B -179.06(15) . . . . ? C12B C13B C14B C15B 0.1(3) . . . . ? F14B C14B C15B C16B 179.67(14) . . . . ? C13B C14B C15B C16B 0.5(3) . . . . ? C14B C15B C16B C11B -0.2(3) . . . . ? C12B C11B C16B C15B -0.6(2) . . . . ? N1B C11B C16B C15B 179.94(15) . . . . ? O1B C1B C21B C22B 177.52(16) . . . . ? N1B C1B C21B C22B -1.8(2) . . . . ? O1B C1B C21B C26B -1.7(2) . . . . ? N1B C1B C21B C26B 178.99(15) . . . . ? C26B C21B C22B N23B 0.5(2) . . . . ? C1B C21B C22B N23B -178.72(14) . . . . ? C21B C22B N23B C24B -1.4(2) . . . . ? C22B N23B C24B C25B 0.5(2) . . . . ? N23B C24B C25B C26B 1.1(3) . . . . ? C24B C25B C26B C21B -2.0(3) . . . . ? C22B C21B C26B C25B 1.2(2) . . . . ? C1B C21B C26B C25B -179.50(15) . . . . ? O1C C1C N1C C11C -0.2(3) . . . . ? C21C C1C N1C C11C -179.60(13) . . . . ? C1C N1C C11C C16C -177.14(15) . . . . ? C1C N1C C11C C12C 3.4(3) . . . . ? C16C C11C C12C C13C -0.1(2) . . . . ? N1C C11C C12C C13C 179.39(15) . . . . ? C11C C12C C13C C14C 0.4(3) . . . . ? C12C C13C C14C C15C -0.3(3) . . . . ? C12C C13C C14C F14C 179.09(15) . . . . ? C13C C14C C15C C16C -0.1(3) . . . . ? F14C C14C C15C C16C -179.49(14) . . . . ? C14C C15C C16C C11C 0.5(2) . . . . ? C12C C11C C16C C15C -0.3(2) . . . . ? N1C C11C C16C C15C -179.84(14) . . . . ? O1C C1C C21C C22C -177.58(15) . . . . ? N1C C1C C21C C22C 1.8(2) . . . . ? O1C C1C C21C C26C 1.8(2) . . . . ? N1C C1C C21C C26C -178.85(14) . . . . ? C26C C21C C22C N23C -0.7(2) . . . . ? C1C C21C C22C N23C 178.68(14) . . . . ? C21C C22C N23C C24C 1.3(2) . . . . ? C22C N23C C24C C25C -0.3(2) . . . . ? N23C C24C C25C C26C -1.2(3) . . . . ? C24C C25C C26C C21C 1.8(3) . . . . ? C22C C21C C26C C25C -0.9(2) . . . . ? C1C C21C C26C C25C 179.65(15) . . . . ? O1D C1D N1D C11D -0.1(3) . . . . ? C21D C1D N1D C11D -179.56(14) . . . . ? C1D N1D C11D C16D 178.42(15) . . . . ? C1D N1D C11D C12D -1.8(3) . . . . ? C16D C11D C12D C13D -1.0(2) . . . . ? N1D C11D C12D C13D 179.21(15) . . . . ? C11D C12D C13D C14D 1.0(3) . . . . ? C12D C13D C14D F14D 179.07(15) . . . . ? C12D C13D C14D C15D -0.2(3) . . . . ? F14D C14D C15D C16D -179.81(14) . . . . ? C13D C14D C15D C16D -0.5(3) . . . . ? C14D C15D C16D C11D 0.5(2) . . . . ? C12D C11D C16D C15D 0.3(2) . . . . ? N1D C11D C16D C15D -179.94(14) . . . . ? O1D C1D C21D C26D 1.4(2) . . . . ? N1D C1D C21D C26D -179.11(14) . . . . ? O1D C1D C21D C22D -177.91(15) . . . . ? N1D C1D C21D C22D 1.5(2) . . . . ? C26D C21D C22D N23D -0.5(2) . . . . ? C1D C21D C22D N23D 178.87(14) . . . . ? C21D C22D N23D C24D 1.4(2) . . . . ? C22D N23D C24D C25D -0.8(2) . . . . ? N23D C24D C25D C26D -0.6(3) . . . . ? C24D C25D C26D C21D 1.5(3) . . . . ? C22D C21D C26D C25D -1.0(2) . . . . ? C1D C21D C26D C25D 179.63(15) . . . . ? loop_ _geom_hbond_atom_site_label_D _geom_hbond_atom_site_label_H _geom_hbond_atom_site_label_A _geom_hbond_distance_DH _geom_hbond_distance_HA _geom_hbond_distance_DA _geom_hbond_angle_DHA _geom_hbond_site_symmetry_A _geom_hbond_publ_flag # # Hydrogen bonding scheme # ======== ======= ====== # # D H A D-H H...A D...A D-H...A symm publ # - - - --- ----- ----- ------- ---- ---- N1A H1A N23D 0.854(19) 2.359(19) 3.193(2) 165.2(16) . yes N1B H1B N23C 0.827(19) 2.42(2) 3.224(2) 165.2(18) . yes N1C H1C N23A 0.865(18) 2.329(19) 3.171(2) 164.4(15) . yes N1D H1D N23B 0.826(19) 2.449(19) 3.254(2) 165.1(16) . yes C16A H16A N23D 0.95 2.53 3.368(2) 148 . yes C16B H16B N23C 0.95 2.53 3.379(2) 150 . yes C16C H16C N23A 0.95 2.52 3.364(2) 147 . yes C16D H16D N23B 0.95 2.53 3.387(2) 150 . yes C22A H22A N23D 0.95 2.44 3.387(2) 178 . yes C22B H22B N23C 0.95 2.43 3.380(2) 177 . yes C22C H22C N23A 0.95 2.42 3.366(2) 177 . yes C22D H22D N23B 0.95 2.45 3.403(2) 176 . yes C12A H12A O1A 0.95 2.23 2.842(2) 122 . yes C12B H12B O1B 0.95 2.24 2.853(2) 121 . yes C12C H12C O1C 0.95 2.23 2.840(2) 122 . yes C12D H12D O1D 0.95 2.24 2.858(2) 122 . yes # A hydrogen bonded tetrameric unit. #========================================================================= data_NmmF_[9-16] _database_code_depnum_ccdc_archive 'CCDC 781756' #TrackingRef '- NxxF-Final04.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common NmmF _chemical_melting_point 395 _chemical_formula_moiety 'C12 H9 F N2 O' _chemical_formula_sum 'C12 H9 F N2 O' _chemical_formula_weight 216.21 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' F F 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Monoclinic _symmetry_space_group_name_H-M 'P 21/n' _symmetry_space_group_name_Hall '-P 2yn' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, y+1/2, -z+1/2' '-x, -y, -z' 'x-1/2, -y-1/2, z-1/2' _cell_length_a 8.8514(6) _cell_length_b 12.1628(10) _cell_length_c 9.6489(5) _cell_angle_alpha 90.00 _cell_angle_beta 105.823(4) _cell_angle_gamma 90.00 _cell_volume 999.42(12) _cell_formula_units_Z 4 _cell_measurement_temperature 150(2) _cell_measurement_reflns_used 4811 _cell_measurement_theta_min 2.55 _cell_measurement_theta_max 27.5 _exptl_crystal_description block _exptl_crystal_colour colourless _exptl_crystal_size_max 0.30 _exptl_crystal_size_mid 0.16 _exptl_crystal_size_min 0.15 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.437 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 448 _exptl_absorpt_coefficient_mu 0.107 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.969 _exptl_absorpt_correction_T_max 0.984 _exptl_absorpt_process_details '(SORTAV; Blessing, 1995)' _exptl_special_details ; ? ; _diffrn_ambient_temperature 150(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed X-ray tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device 'Nonius KappaCCD' _diffrn_measurement_method '\f, \w scans with \k offsets' _diffrn_standards_number ? _diffrn_standards_decay_% ? _diffrn_reflns_number 6578 _diffrn_reflns_av_R_equivalents 0.0340 _diffrn_reflns_av_sigmaI/netI 0.0468 _diffrn_reflns_limit_h_min -11 _diffrn_reflns_limit_h_max 11 _diffrn_reflns_limit_k_min -15 _diffrn_reflns_limit_k_max 15 _diffrn_reflns_limit_l_min -12 _diffrn_reflns_limit_l_max 12 _diffrn_reflns_theta_min 2.76 _diffrn_reflns_theta_max 27.47 _diffrn_measured_fraction_theta_max 0.991 _diffrn_reflns_theta_full 27.47 _diffrn_measured_fraction_theta_full 0.991 _reflns_number_total 2271 _reflns_number_gt 1595 _reflns_threshold_expression I>2\s(I) _computing_data_collection 'kappaCCD Server software (Nonius, 1997)' _computing_cell_refinement 'DENZO-SMN (Otwinowski and Minor, 1997)' _computing_data_reduction 'DENZO-SMN (Otwinowski and Minor, 1997)' _computing_structure_solution 'SHELXS97 (Sheldrick, 2008)' _computing_structure_refinement 'SHELXL97 (Sheldrick, 2008) and SORTX (McArdle, 1995)' _computing_molecular_graphics 'PLATON (Spek, 2009)' _computing_publication_material 'SHELXL97 and PREP8 (Ferguson, 1998)' _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 'w=1/[\s^2^(Fo^2^)+(0.0584P)^2^+0.1062P] 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 SHELXL _refine_ls_extinction_coef 0.013(3) _refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^ _refine_ls_number_reflns 2271 _refine_ls_number_parameters 150 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0746 _refine_ls_R_factor_gt 0.0444 _refine_ls_wR_factor_ref 0.1181 _refine_ls_wR_factor_gt 0.1023 _refine_ls_goodness_of_fit_ref 1.050 _refine_ls_restrained_S_all 1.050 _refine_ls_shift/su_max 0.000 _refine_ls_shift/su_mean 0.000 _refine_diff_density_max 0.221 _refine_diff_density_min -0.248 _refine_diff_density_rms 0.049 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 F13 F 0.25794(13) 0.86360(8) 0.48213(11) 0.0471(3) Uani 1 1 d . . . O1 O 0.07226(13) 0.49631(9) 0.34025(11) 0.0333(3) Uani 1 1 d . . . C1 C 0.16919(17) 0.43609(12) 0.41945(15) 0.0245(4) Uani 1 1 d . . . N1 N 0.27518(16) 0.47110(11) 0.54215(13) 0.0264(3) Uani 1 1 d . . . H1 H 0.332(2) 0.4208(15) 0.6018(18) 0.037(5) Uiso 1 1 d . . . C11 C 0.29358(17) 0.58010(13) 0.59558(16) 0.0249(4) Uani 1 1 d . . . C12 C 0.25655(17) 0.67203(13) 0.50699(16) 0.0272(4) Uani 1 1 d . . . H12 H 0.2090 0.6648 0.4065 0.033 Uiso 1 1 calc R . . C13 C 0.29121(19) 0.77385(13) 0.57000(18) 0.0305(4) Uani 1 1 d . . . C14 C 0.35979(18) 0.79070(14) 0.71412(18) 0.0326(4) Uani 1 1 d . . . H14 H 0.3831 0.8625 0.7526 0.039 Uiso 1 1 calc R . . C15 C 0.39335(18) 0.69834(14) 0.80071(17) 0.0315(4) Uani 1 1 d . . . H15 H 0.4401 0.7067 0.9012 0.038 Uiso 1 1 calc R . . C16 C 0.36006(18) 0.59392(14) 0.74348(16) 0.0286(4) Uani 1 1 d . . . H16 H 0.3825 0.5315 0.8049 0.034 Uiso 1 1 calc R . . C21 C 0.17692(17) 0.31625(12) 0.38614(15) 0.0227(3) Uani 1 1 d . . . C22 C 0.04210(18) 0.26677(12) 0.30045(16) 0.0253(4) Uani 1 1 d . . . H22 H -0.0482 0.3113 0.2643 0.030 Uiso 1 1 calc R . . N23 N 0.03220(15) 0.15999(10) 0.26592(13) 0.0282(3) Uani 1 1 d . . . C24 C 0.16142(18) 0.09902(14) 0.31788(16) 0.0282(4) Uani 1 1 d . . . H24 H 0.1561 0.0227 0.2964 0.034 Uiso 1 1 calc R . . C25 C 0.30150(19) 0.14102(13) 0.40078(16) 0.0291(4) Uani 1 1 d . . . H25 H 0.3907 0.0948 0.4335 0.035 Uiso 1 1 calc R . . C26 C 0.30999(18) 0.25137(13) 0.43544(15) 0.0267(4) Uani 1 1 d . . . H26 H 0.4053 0.2825 0.4921 0.032 Uiso 1 1 calc R . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 F13 0.0549(7) 0.0237(6) 0.0566(7) 0.0049(5) 0.0045(5) -0.0045(5) O1 0.0300(7) 0.0249(6) 0.0362(6) 0.0036(5) -0.0057(5) 0.0024(5) C1 0.0222(8) 0.0229(8) 0.0261(7) 0.0017(6) 0.0024(6) -0.0014(6) N1 0.0280(7) 0.0202(7) 0.0257(7) -0.0007(6) -0.0015(5) 0.0024(6) C11 0.0188(8) 0.0240(8) 0.0302(8) -0.0046(7) 0.0038(6) 0.0000(6) C12 0.0238(8) 0.0248(9) 0.0310(8) -0.0005(7) 0.0039(6) -0.0011(6) C13 0.0266(9) 0.0220(9) 0.0417(10) 0.0017(7) 0.0074(7) -0.0005(7) C14 0.0224(9) 0.0290(9) 0.0455(10) -0.0119(8) 0.0074(7) -0.0030(7) C15 0.0224(8) 0.0385(10) 0.0316(8) -0.0095(7) 0.0037(6) 0.0006(7) C16 0.0245(8) 0.0303(9) 0.0287(8) -0.0022(7) 0.0033(6) 0.0032(7) C21 0.0230(8) 0.0220(8) 0.0217(7) 0.0022(6) 0.0036(6) -0.0003(6) C22 0.0242(8) 0.0234(8) 0.0258(8) 0.0009(6) 0.0025(6) 0.0010(6) N23 0.0273(7) 0.0242(7) 0.0307(7) -0.0014(6) 0.0038(5) -0.0012(6) C24 0.0304(9) 0.0219(8) 0.0314(8) -0.0015(7) 0.0069(7) 0.0008(7) C25 0.0270(9) 0.0267(9) 0.0308(8) 0.0009(7) 0.0033(6) 0.0061(7) C26 0.0217(8) 0.0289(9) 0.0266(8) -0.0017(7) 0.0016(6) -0.0018(6) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag F13 C13 1.3642(19) . ? O1 C1 1.2244(18) . ? C1 N1 1.3629(19) . ? C1 C21 1.498(2) . ? N1 C11 1.416(2) . ? N1 H1 0.896(18) . ? C11 C12 1.391(2) . ? C11 C16 1.398(2) . ? C12 C13 1.377(2) . ? C12 H12 0.9500 . ? C13 C14 1.373(2) . ? C14 C15 1.383(2) . ? C14 H14 0.9500 . ? C15 C16 1.384(2) . ? C15 H15 0.9500 . ? C16 H16 0.9500 . ? C21 C26 1.390(2) . ? C21 C22 1.390(2) . ? C22 N23 1.3377(19) . ? C22 H22 0.9500 . ? N23 C24 1.340(2) . ? C24 C25 1.377(2) . ? C24 H24 0.9500 . ? C25 C26 1.380(2) . ? C25 H25 0.9500 . ? C26 H26 0.9500 . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag O1 C1 N1 123.68(14) . . ? O1 C1 C21 120.88(13) . . ? N1 C1 C21 115.44(13) . . ? C1 N1 C11 126.33(13) . . ? C1 N1 H1 118.6(11) . . ? C11 N1 H1 114.6(11) . . ? C12 C11 C16 119.59(14) . . ? C12 C11 N1 122.99(13) . . ? C16 C11 N1 117.32(13) . . ? C13 C12 C11 117.70(14) . . ? C13 C12 H12 121.2 . . ? C11 C12 H12 121.2 . . ? F13 C13 C14 118.11(14) . . ? F13 C13 C12 117.45(14) . . ? C14 C13 C12 124.43(15) . . ? C13 C14 C15 116.97(15) . . ? C13 C14 H14 121.5 . . ? C15 C14 H14 121.5 . . ? C14 C15 C16 121.13(14) . . ? C14 C15 H15 119.4 . . ? C16 C15 H15 119.4 . . ? C15 C16 C11 120.15(14) . . ? C15 C16 H16 119.9 . . ? C11 C16 H16 119.9 . . ? C26 C21 C22 117.90(14) . . ? C26 C21 C1 124.27(14) . . ? C22 C21 C1 117.83(13) . . ? N23 C22 C21 123.77(14) . . ? N23 C22 H22 118.1 . . ? C21 C22 H22 118.1 . . ? C22 N23 C24 116.92(13) . . ? N23 C24 C25 123.59(15) . . ? N23 C24 H24 118.2 . . ? C25 C24 H24 118.2 . . ? C24 C25 C26 118.83(14) . . ? C24 C25 H25 120.6 . . ? C26 C25 H25 120.6 . . ? C25 C26 C21 118.96(14) . . ? C25 C26 H26 120.5 . . ? C21 C26 H26 120.5 . . ? 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 C1 N1 C11 -1.7(2) . . . . ? C21 C1 N1 C11 178.79(13) . . . . ? C1 N1 C11 C12 -28.1(2) . . . . ? C1 N1 C11 C16 155.48(15) . . . . ? C16 C11 C12 C13 1.5(2) . . . . ? N1 C11 C12 C13 -174.89(14) . . . . ? C11 C12 C13 F13 178.54(13) . . . . ? C11 C12 C13 C14 0.0(2) . . . . ? F13 C13 C14 C15 -179.55(13) . . . . ? C12 C13 C14 C15 -1.0(3) . . . . ? C13 C14 C15 C16 0.5(2) . . . . ? C14 C15 C16 C11 1.0(2) . . . . ? C12 C11 C16 C15 -2.0(2) . . . . ? N1 C11 C16 C15 174.58(13) . . . . ? O1 C1 C21 C26 156.16(15) . . . . ? N1 C1 C21 C26 -24.3(2) . . . . ? O1 C1 C21 C22 -23.9(2) . . . . ? N1 C1 C21 C22 155.64(14) . . . . ? C26 C21 C22 N23 1.7(2) . . . . ? C1 C21 C22 N23 -178.19(13) . . . . ? C21 C22 N23 C24 -0.2(2) . . . . ? C22 N23 C24 C25 -1.4(2) . . . . ? N23 C24 C25 C26 1.3(2) . . . . ? C24 C25 C26 C21 0.3(2) . . . . ? C22 C21 C26 C25 -1.7(2) . . . . ? C1 C21 C26 C25 178.22(14) . . . . ? loop_ _geom_hbond_atom_site_label_D _geom_hbond_atom_site_label_H _geom_hbond_atom_site_label_A _geom_hbond_distance_DH _geom_hbond_distance_HA _geom_hbond_distance_DA _geom_hbond_angle_DHA _geom_hbond_site_symmetry_A _geom_hbond_publ_flag # # Hydrogen bonding scheme # ======== ======= ====== # # D H A D-H H...A D...A D-H...A symm publ # - - - --- ----- ----- ------- ---- ---- N1 H1 N23 0.896(18) 2.253(19) 3.1146(18) 161.3(16) 4_666 yes C12 H12 O1 0.95 2.38 2.8959(19) 114 . yes C14 H14 O1 0.95 2.39 3.2375(19) 149 4_676 yes C15 H15 Cg1 0.95 2.82 3.5574(17) 135 2_556 yes C22 H22 Cg2 0.95 2.77 3.4486(18) 129 3_566 yes #========================================================================= data_NopF_9-04] _database_code_depnum_ccdc_archive 'CCDC 781757' #TrackingRef '- NxxF-Final04.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common NopF _chemical_melting_point 367 _chemical_formula_moiety 'C12 H8.96 Cl0.04 F N2 O' _chemical_formula_sum 'C12 H8.96 Cl0.04 F N2 O' _chemical_formula_weight 217.68 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' F F 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Monoclinic _symmetry_space_group_name_H-M 'P 21/c' _symmetry_space_group_name_Hall '-P 2ybc' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y-1/2, z-1/2' _cell_length_a 8.0622(9) _cell_length_b 6.0665(4) _cell_length_c 20.392(2) _cell_angle_alpha 90.00 _cell_angle_beta 95.296(4) _cell_angle_gamma 90.00 _cell_volume 993.10(16) _cell_formula_units_Z 4 _cell_measurement_temperature 150(2) _cell_measurement_reflns_used 11385 _cell_measurement_theta_min 2.55 _cell_measurement_theta_max 27.5 _exptl_crystal_description block _exptl_crystal_colour colourless _exptl_crystal_size_max 0.34 _exptl_crystal_size_mid 0.20 _exptl_crystal_size_min 0.03 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.456 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 451.2 _exptl_absorpt_coefficient_mu 0.119 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.9606 _exptl_absorpt_correction_T_max 0.9964 _exptl_absorpt_process_details '(SORTAV; Blessing, 1995)' _exptl_special_details ; ? ; _diffrn_ambient_temperature 150(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed X-ray tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device 'Nonius KappaCCD' _diffrn_measurement_method '\f, \w scans with \k offsets' _diffrn_standards_number 6521 _diffrn_standards_decay_% ? _diffrn_reflns_number 6521 _diffrn_reflns_av_R_equivalents 0.1009 _diffrn_reflns_av_sigmaI/netI 0.1018 _diffrn_reflns_limit_h_min -10 _diffrn_reflns_limit_h_max 10 _diffrn_reflns_limit_k_min -6 _diffrn_reflns_limit_k_max 7 _diffrn_reflns_limit_l_min -20 _diffrn_reflns_limit_l_max 26 _diffrn_reflns_theta_min 3.09 _diffrn_reflns_theta_max 27.56 _diffrn_measured_fraction_theta_max 0.975 _diffrn_reflns_theta_full 27.56 _diffrn_measured_fraction_theta_full 0.975 _reflns_number_total 2234 _reflns_number_gt 1187 _reflns_threshold_expression I>2\s(I) _computing_data_collection 'kappaCCD Server software (Nonius, 1997)' _computing_cell_refinement 'DENZO-SMN (Otwinowski and Minor, 1997)' _computing_data_reduction 'DENZO-SMN (Otwinowski and Minor, 1997)' _computing_structure_solution 'SHELXS97 (Sheldrick, 2008)' _computing_structure_refinement 'SHELXL97 (Sheldrick, 2008) and SORTX (McArdle, 1995)' _computing_molecular_graphics 'PLATON (Spek, 2003)' _computing_publication_material 'SHELXL97 and PREP8 (Ferguson, 1998)' _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 'w=1/[\s^2^(Fo^2^)+(0.0473P)^2^+0.4318P] 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 2234 _refine_ls_number_parameters 154 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.1420 _refine_ls_R_factor_gt 0.0634 _refine_ls_wR_factor_ref 0.1656 _refine_ls_wR_factor_gt 0.1333 _refine_ls_goodness_of_fit_ref 1.029 _refine_ls_restrained_S_all 1.029 _refine_ls_shift/su_max 0.000 _refine_ls_shift/su_mean 0.000 _refine_diff_density_max 0.192 _refine_diff_density_min -0.239 _refine_diff_density_rms 0.044 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 F14 F 0.4930(2) 0.1504(3) 0.88278(8) 0.0598(5) Uani 1 1 d . A -1 O1 O 0.0747(2) -0.3521(3) 0.64264(10) 0.0530(6) Uani 1 1 d . A -1 C1 C 0.0164(3) -0.1699(4) 0.62793(13) 0.0412(6) Uani 1 1 d . A -1 N1 N 0.0586(3) 0.0191(4) 0.66073(11) 0.0421(6) Uani 1 1 d . A -1 H1 H 0.013(4) 0.140(5) 0.6411(15) 0.063(9) Uiso 1 1 d . B -1 C11 C 0.1738(3) 0.0444(4) 0.71687(13) 0.0388(6) Uani 1 1 d . A -1 C12 C 0.2051(3) -0.1231(4) 0.76270(14) 0.0431(7) Uani 1 1 d . A -1 H12 H 0.1534 -0.2628 0.7557 0.052 Uiso 1 1 calc R A -1 C13 C 0.3117(3) -0.0858(4) 0.81853(14) 0.0460(7) Uani 1 1 d . A -1 H13 H 0.3321 -0.1986 0.8506 0.055 Uiso 1 1 calc R A -1 C14 C 0.3878(3) 0.1153(4) 0.82734(14) 0.0445(7) Uani 1 1 d . A -1 C15 C 0.3604(3) 0.2829(4) 0.78288(14) 0.0455(7) Uani 1 1 d . A -1 H15 H 0.4141 0.4213 0.7901 0.055 Uiso 1 1 calc R A -1 C16 C 0.2524(3) 0.2464(4) 0.72698(14) 0.0453(7) Uani 1 1 d . A -1 H16 H 0.2321 0.3607 0.6954 0.054 Uiso 1 1 calc R A -1 C21 C -0.1066(3) -0.1412(4) 0.56841(13) 0.0395(6) Uani 1 1 d . A -1 N22 N -0.1663(3) 0.0633(4) 0.55633(11) 0.0443(6) Uani 1 1 d . A -1 C23 C -0.2721(3) 0.0880(4) 0.50236(15) 0.0479(7) Uani 1 1 d . A -1 H23 H -0.3185 0.2299 0.4934 0.057 Uiso 1 1 calc R A -1 C24 C -0.3179(4) -0.0802(5) 0.45894(15) 0.0489(7) Uani 1 1 d . A -1 H24 H -0.3911 -0.0532 0.4206 0.059 Uiso 1 1 calc R A -1 C25 C -0.2554(4) -0.2876(5) 0.47237(15) 0.0505(8) Uani 1 1 d . A -1 H25 H -0.2842 -0.4069 0.4433 0.061 Uiso 0.958(4) 1 calc PR C -1 C26 C -0.1500(3) -0.3195(4) 0.52888(14) 0.0465(7) Uani 1 1 d . A -1 H26 H -0.1083 -0.4622 0.5403 0.056 Uiso 1 1 calc R A -1 Cl25 Cl -0.339(3) -0.403(4) 0.4352(13) 0.089(11) Uiso 0.042(4) 1 d P C -2 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 F14 0.0547(11) 0.0672(11) 0.0539(11) -0.0028(8) -0.0148(9) -0.0011(8) O1 0.0539(12) 0.0478(12) 0.0552(13) 0.0000(9) -0.0067(10) 0.0105(10) C1 0.0347(15) 0.0476(16) 0.0417(16) 0.0001(13) 0.0064(12) 0.0015(13) N1 0.0393(14) 0.0435(14) 0.0427(15) 0.0026(11) -0.0008(11) 0.0058(10) C11 0.0299(14) 0.0460(15) 0.0410(16) 0.0000(12) 0.0060(12) 0.0055(12) C12 0.0394(15) 0.0453(15) 0.0445(17) 0.0033(13) 0.0045(13) -0.0008(12) C13 0.0430(17) 0.0495(17) 0.0450(18) 0.0055(12) 0.0017(14) 0.0032(13) C14 0.0354(15) 0.0543(18) 0.0434(17) -0.0028(13) 0.0002(13) 0.0026(13) C15 0.0396(16) 0.0447(15) 0.0520(19) -0.0027(13) 0.0030(14) -0.0014(12) C16 0.0457(17) 0.0412(15) 0.0491(18) 0.0034(12) 0.0042(14) 0.0041(13) C21 0.0322(14) 0.0435(15) 0.0431(17) 0.0050(12) 0.0050(12) 0.0006(12) N22 0.0366(13) 0.0485(13) 0.0470(14) 0.0025(11) 0.0005(11) 0.0025(10) C23 0.0399(16) 0.0461(16) 0.0571(19) 0.0068(14) 0.0019(14) 0.0010(12) C24 0.0426(17) 0.0535(18) 0.0492(18) 0.0039(13) -0.0036(14) -0.0035(13) C25 0.0481(18) 0.0513(18) 0.0512(19) -0.0041(14) 0.0005(15) -0.0087(14) C26 0.0459(17) 0.0446(16) 0.0484(18) 0.0033(13) 0.0016(14) 0.0006(13) _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 F14 C14 1.366(3) . ? O1 C1 1.227(3) . ? C1 N1 1.355(3) . ? C1 C21 1.505(4) . ? N1 C11 1.414(3) . ? N1 H1 0.90(3) . ? C11 C16 1.386(4) . ? C11 C12 1.388(4) . ? C12 C13 1.380(4) . ? C12 H12 0.9500 . ? C13 C14 1.370(4) . ? C13 H13 0.9500 . ? C14 C15 1.366(4) . ? C15 C16 1.387(4) . ? C15 H15 0.9500 . ? C16 H16 0.9500 . ? C21 N22 1.345(3) . ? C21 C26 1.375(4) . ? N22 C23 1.337(3) . ? C23 C24 1.379(4) . ? C23 H23 0.9500 . ? C24 C25 1.374(4) . ? C24 H24 0.9500 . ? C25 C26 1.381(4) . ? C25 H25 0.9500 . ? C26 H26 0.9500 . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag O1 C1 N1 124.6(3) . . ? O1 C1 C21 120.7(2) . . ? N1 C1 C21 114.7(2) . . ? C1 N1 C11 127.4(2) . . ? C1 N1 H1 113.5(19) . . ? C11 N1 H1 118.8(19) . . ? C16 C11 C12 119.7(3) . . ? C16 C11 N1 118.2(2) . . ? C12 C11 N1 122.1(2) . . ? C13 C12 C11 119.8(2) . . ? C13 C12 H12 120.1 . . ? C11 C12 H12 120.1 . . ? C14 C13 C12 119.4(3) . . ? C14 C13 H13 120.3 . . ? C12 C13 H13 120.3 . . ? F14 C14 C15 118.9(2) . . ? F14 C14 C13 118.9(2) . . ? C15 C14 C13 122.2(3) . . ? C14 C15 C16 118.5(3) . . ? C14 C15 H15 120.7 . . ? C16 C15 H15 120.7 . . ? C11 C16 C15 120.5(3) . . ? C11 C16 H16 119.8 . . ? C15 C16 H16 119.8 . . ? N22 C21 C26 123.4(2) . . ? N22 C21 C1 116.9(2) . . ? C26 C21 C1 119.7(2) . . ? C23 N22 C21 116.4(2) . . ? N22 C23 C24 123.9(3) . . ? N22 C23 H23 118.0 . . ? C24 C23 H23 118.0 . . ? C25 C24 C23 118.6(3) . . ? C25 C24 H24 120.7 . . ? C23 C24 H24 120.7 . . ? C24 C25 C26 118.7(3) . . ? C24 C25 H25 120.6 . . ? C26 C25 H25 120.6 . . ? C21 C26 C25 118.9(3) . . ? C21 C26 H26 120.6 . . ? C25 C26 H26 120.6 . . ? 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 C1 N1 C11 -0.3(4) . . . . ? C21 C1 N1 C11 -178.1(2) . . . . ? C1 N1 C11 C16 153.2(3) . . . . ? C1 N1 C11 C12 -29.2(4) . . . . ? C16 C11 C12 C13 1.2(4) . . . . ? N1 C11 C12 C13 -176.4(2) . . . . ? C11 C12 C13 C14 -1.3(4) . . . . ? C12 C13 C14 F14 180.0(2) . . . . ? C12 C13 C14 C15 0.8(4) . . . . ? F14 C14 C15 C16 -179.5(2) . . . . ? C13 C14 C15 C16 -0.3(4) . . . . ? C12 C11 C16 C15 -0.7(4) . . . . ? N1 C11 C16 C15 177.0(2) . . . . ? C14 C15 C16 C11 0.3(4) . . . . ? O1 C1 C21 N22 179.0(2) . . . . ? N1 C1 C21 N22 -3.1(3) . . . . ? O1 C1 C21 C26 -2.2(4) . . . . ? N1 C1 C21 C26 175.7(2) . . . . ? C26 C21 N22 C23 -0.5(4) . . . . ? C1 C21 N22 C23 178.3(2) . . . . ? C21 N22 C23 C24 -1.8(4) . . . . ? N22 C23 C24 C25 1.9(4) . . . . ? C23 C24 C25 C26 0.3(4) . . . . ? N22 C21 C26 C25 2.5(4) . . . . ? C1 C21 C26 C25 -176.2(2) . . . . ? C24 C25 C26 C21 -2.3(4) . . . . ? loop_ _geom_hbond_atom_site_label_D _geom_hbond_atom_site_label_H _geom_hbond_atom_site_label_A _geom_hbond_distance_DH _geom_hbond_distance_HA _geom_hbond_distance_DA _geom_hbond_angle_DHA _geom_hbond_site_symmetry_A _geom_hbond_publ_flag # # Hydrogen bonding scheme # ======== ======= ====== # # D H A D-H H...A D...A D-H...A symm publ # - - - --- ----- ----- ------- ---- ---- N1 H1 N22 0.90(3) 2.20(3) 2.679(3) 113(2) . yes C12 H12 O1 0.95 2.40 2.925(3) 115 . yes C16 H16 O1 0.95 2.36 3.238(3) 154 1_565 yes C25 H25 F14 0.95 2.55 3.408(3) 150 4_455 yes #===================================================================== data_NomF_[9-07] _database_code_depnum_ccdc_archive 'CCDC 781758' #TrackingRef '- NxxF-Final04.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common NomF _chemical_melting_point 351 _chemical_formula_moiety 'C12 H9 F N2 O' _chemical_formula_sum 'C12 H9 F N2 O' _chemical_formula_weight 216.21 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' F F 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Monoclinic _symmetry_space_group_name_H-M 'P 21/n' _symmetry_space_group_name_Hall '-P 2yn' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, y+1/2, -z+1/2' '-x, -y, -z' 'x-1/2, -y-1/2, z-1/2' _cell_length_a 5.7289(2) _cell_length_b 23.2077(13) _cell_length_c 15.1001(9) _cell_angle_alpha 90.00 _cell_angle_beta 95.260(3) _cell_angle_gamma 90.00 _cell_volume 1999.17(18) _cell_formula_units_Z 8 _cell_measurement_temperature 150(2) _cell_measurement_reflns_used 7698 _cell_measurement_theta_min 2.55 _cell_measurement_theta_max 27.5 _exptl_crystal_description block _exptl_crystal_colour colourless _exptl_crystal_size_max 0.26 _exptl_crystal_size_mid 0.16 _exptl_crystal_size_min 0.14 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.437 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 896 _exptl_absorpt_coefficient_mu 0.107 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.9728 _exptl_absorpt_correction_T_max 0.9852 _exptl_absorpt_process_details '(SORTAV; Blessing, 1995)' _exptl_special_details ; ? ; _diffrn_ambient_temperature 150(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed X-ray tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device 'Nonius KappaCCD' _diffrn_measurement_method '\f, \w scans with \k offsets' _diffrn_standards_number 13916 _diffrn_standards_decay_% ? _diffrn_reflns_number 13916 _diffrn_reflns_av_R_equivalents 0.0731 _diffrn_reflns_av_sigmaI/netI 0.1066 _diffrn_reflns_limit_h_min -7 _diffrn_reflns_limit_h_max 7 _diffrn_reflns_limit_k_min -26 _diffrn_reflns_limit_k_max 29 _diffrn_reflns_limit_l_min -19 _diffrn_reflns_limit_l_max 19 _diffrn_reflns_theta_min 2.71 _diffrn_reflns_theta_max 27.50 _diffrn_measured_fraction_theta_max 0.967 _diffrn_reflns_theta_full 27.50 _diffrn_measured_fraction_theta_full 0.967 _reflns_number_total 4454 _reflns_number_gt 2033 _reflns_threshold_expression I>2\s(I) _computing_data_collection 'kappaCCD Server software (Nonius, 1997)' _computing_cell_refinement 'DENZO-SMN (Otwinowski and Minor, 1997)' _computing_data_reduction 'DENZO-SMN (Otwinowski and Minor, 1997)' _computing_structure_solution 'SHELXS97 (Sheldrick, 2008)' _computing_structure_refinement 'SHELXL97 (Sheldrick, 2008) and SORTX (McArdle, 1995)' _computing_molecular_graphics 'PLATON (Spek, 2009)' _computing_publication_material 'SHELXL97 and PREP8 (Ferguson, 1998)' _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 'w=1/[\s^2^(Fo^2^)+(0.1008P)^2^+0.2096P] 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 4454 _refine_ls_number_parameters 307 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.1900 _refine_ls_R_factor_gt 0.0742 _refine_ls_wR_factor_ref 0.2230 _refine_ls_wR_factor_gt 0.1620 _refine_ls_goodness_of_fit_ref 1.067 _refine_ls_restrained_S_all 1.067 _refine_ls_shift/su_max 0.000 _refine_ls_shift/su_mean 0.000 _refine_diff_density_max 0.359 _refine_diff_density_min -0.296 _refine_diff_density_rms 0.072 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 O1A O -0.1704(4) 0.21163(11) 0.75737(16) 0.0505(7) Uani 1 1 d . . . C1A C 0.0059(5) 0.21535(14) 0.7169(2) 0.0356(8) Uani 1 1 d . A . N1A N 0.1876(4) 0.17837(12) 0.72506(18) 0.0359(7) Uani 1 1 d . . . H1A H 0.321(5) 0.1872(15) 0.689(2) 0.050(10) Uiso 1 1 d . . . C11A C 0.2196(5) 0.13030(14) 0.7823(2) 0.0337(8) Uani 1 1 d . A -1 C12A C 0.0631(5) 0.11613(15) 0.8440(2) 0.0392(9) Uani 1 1 d . A -1 H12A H -0.0733 0.1386 0.8496 0.047 Uiso 1 1 calc R A -1 C13A C 0.1120(5) 0.06844(15) 0.8969(2) 0.0394(9) Uani 1 1 d . A -1 H13A H 0.0052 0.0589 0.9391 0.047 Uiso 0.061(5) 1 calc PR B -1 C14A C 0.3047(5) 0.03394(15) 0.8925(2) 0.0412(9) Uani 1 1 d . A -1 H14A H 0.3315 0.0013 0.9299 0.049 Uiso 1 1 calc R A -1 C15A C 0.4584(5) 0.04895(15) 0.8308(2) 0.0397(9) Uani 1 1 d . A -1 H15A H 0.5937 0.0260 0.8256 0.048 Uiso 0.939(5) 1 calc PR B -1 C16A C 0.4195(5) 0.09675(15) 0.7766(2) 0.0386(8) Uani 1 1 d . A -1 H16A H 0.5290 0.1067 0.7355 0.046 Uiso 1 1 calc R A -1 F13A F -0.0392(3) 0.05588(10) 0.95865(15) 0.0553(8) Uani 0.939(5) 1 d P B -2 F15A F 0.635(4) 0.0114(12) 0.8301(17) 0.033(10) Uani 0.061(5) 1 d P B -2 C21A C 0.0323(5) 0.26428(14) 0.6528(2) 0.0325(8) Uani 1 1 d . . . N22A N 0.2295(4) 0.26493(12) 0.61060(18) 0.0395(7) Uani 1 1 d . A . C23A C 0.2502(6) 0.30810(16) 0.5530(2) 0.0454(9) Uani 1 1 d . . . H23A H 0.3864 0.3092 0.5216 0.055 Uiso 1 1 calc R A . C24A C 0.0853(5) 0.35100(15) 0.5366(2) 0.0430(9) Uani 1 1 d . A . H24A H 0.1080 0.3807 0.4950 0.052 Uiso 1 1 calc R . . C25A C -0.1113(6) 0.34998(15) 0.5814(2) 0.0415(9) Uani 1 1 d . . . H25A H -0.2266 0.3793 0.5720 0.050 Uiso 1 1 calc R A . C26A C -0.1401(5) 0.30565(15) 0.6407(2) 0.0399(9) Uani 1 1 d . A . H26A H -0.2758 0.3038 0.6723 0.048 Uiso 1 1 calc R . . F13B F 0.8958(3) -0.07614(10) 0.79059(14) 0.0638(7) Uani 1 1 d . . . O1B O 0.7354(4) 0.08726(11) 0.60018(15) 0.0449(7) Uani 1 1 d . . . C1B C 0.9143(5) 0.09406(14) 0.5624(2) 0.0354(8) Uani 1 1 d . . . N1B N 1.1066(4) 0.06016(12) 0.57311(18) 0.0358(7) Uani 1 1 d . . . H1B H 1.223(5) 0.0708(13) 0.532(2) 0.039(9) Uiso 1 1 d . . . C11B C 1.1445(5) 0.00958(14) 0.6248(2) 0.0343(8) Uani 1 1 d . . . C12B C 0.9887(5) -0.00926(15) 0.6838(2) 0.0383(8) Uani 1 1 d . . . H12B H 0.8478 0.0110 0.6911 0.046 Uiso 1 1 calc R . . C13B C 1.0473(6) -0.05868(16) 0.7313(2) 0.0436(9) Uani 1 1 d . . . C14B C 1.2455(6) -0.09003(16) 0.7237(2) 0.0442(9) Uani 1 1 d . . . H14B H 1.2783 -0.1239 0.7580 0.053 Uiso 1 1 calc R . . C15B C 1.3965(6) -0.07063(15) 0.6642(2) 0.0408(9) Uani 1 1 d . . . H15B H 1.5358 -0.0916 0.6568 0.049 Uiso 1 1 calc R . . C16B C 1.3481(5) -0.02128(14) 0.6155(2) 0.0361(8) Uani 1 1 d . . . H16B H 1.4547 -0.0083 0.5752 0.043 Uiso 1 1 calc R . . C21B C 0.9352(5) 0.14331(14) 0.4991(2) 0.0343(8) Uani 1 1 d . . . N22B N 1.1305(4) 0.14498(12) 0.45630(18) 0.0359(7) Uani 1 1 d . . . C23B C 1.1472(5) 0.18807(15) 0.3980(2) 0.0398(9) Uani 1 1 d . . . H23B H 1.2835 0.1902 0.3667 0.048 Uiso 1 1 calc R . . C24B C 0.9754(5) 0.22958(15) 0.3810(2) 0.0393(9) Uani 1 1 d . . . H24B H 0.9938 0.2593 0.3390 0.047 Uiso 1 1 calc R . . C25B C 0.7777(5) 0.22710(15) 0.4262(2) 0.0394(9) Uani 1 1 d . . . H25B H 0.6580 0.2553 0.4162 0.047 Uiso 1 1 calc R . . C26B C 0.7558(5) 0.18307(15) 0.4862(2) 0.0356(8) Uani 1 1 d . . . H26B H 0.6205 0.1801 0.5179 0.043 Uiso 1 1 calc R . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 O1A 0.0446(14) 0.0491(17) 0.0606(18) 0.0100(13) 0.0195(12) 0.0097(11) C1A 0.0353(19) 0.033(2) 0.038(2) -0.0004(16) 0.0034(15) -0.0026(14) N1A 0.0337(15) 0.0381(18) 0.0359(17) -0.0003(14) 0.0038(12) 0.0007(12) C11A 0.0328(17) 0.031(2) 0.037(2) -0.0063(16) -0.0024(14) -0.0053(14) C12A 0.0383(18) 0.041(2) 0.039(2) -0.0047(18) 0.0063(15) -0.0019(15) C13A 0.0381(19) 0.043(2) 0.038(2) 0.0030(18) 0.0089(15) -0.0048(16) C14A 0.0413(19) 0.038(2) 0.043(2) 0.0023(18) -0.0052(15) -0.0021(16) C15A 0.0347(19) 0.040(2) 0.043(2) -0.0073(18) -0.0022(15) 0.0064(15) C16A 0.0318(18) 0.043(2) 0.041(2) -0.0041(18) 0.0012(14) -0.0023(15) F13A 0.0516(13) 0.0588(16) 0.0578(16) 0.0168(12) 0.0183(11) 0.0038(11) F15A 0.037(17) 0.04(2) 0.022(17) 0.008(13) 0.002(12) 0.004(13) C21A 0.0326(18) 0.033(2) 0.0319(19) -0.0053(15) 0.0007(13) -0.0043(14) N22A 0.0356(16) 0.0436(19) 0.0396(18) 0.0029(15) 0.0046(12) -0.0025(12) C23A 0.0411(19) 0.050(3) 0.046(2) 0.007(2) 0.0083(16) -0.0066(17) C24A 0.046(2) 0.037(2) 0.045(2) 0.0046(17) -0.0001(16) -0.0011(16) C25A 0.042(2) 0.038(2) 0.044(2) -0.0024(18) 0.0006(15) 0.0066(15) C26A 0.0371(18) 0.042(2) 0.040(2) -0.0048(19) 0.0017(14) -0.0007(15) F13B 0.0520(13) 0.0755(18) 0.0645(16) 0.0323(13) 0.0090(11) -0.0055(11) O1B 0.0384(13) 0.0521(17) 0.0458(16) 0.0079(12) 0.0123(11) 0.0025(11) C1B 0.0333(19) 0.037(2) 0.035(2) -0.0037(16) 0.0003(14) -0.0033(14) N1B 0.0340(15) 0.0352(17) 0.0384(17) 0.0021(14) 0.0049(12) 0.0013(12) C11B 0.0370(18) 0.030(2) 0.034(2) -0.0009(16) -0.0043(14) -0.0013(14) C12B 0.0363(18) 0.041(2) 0.037(2) 0.0026(17) -0.0009(14) -0.0049(15) C13B 0.044(2) 0.049(2) 0.038(2) 0.0095(19) 0.0017(16) -0.0100(17) C14B 0.049(2) 0.040(2) 0.040(2) 0.0017(18) -0.0140(16) -0.0040(17) C15B 0.0395(19) 0.040(2) 0.041(2) -0.0023(18) -0.0033(15) 0.0010(15) C16B 0.0359(18) 0.039(2) 0.033(2) -0.0028(16) 0.0007(14) -0.0016(15) C21B 0.0355(18) 0.035(2) 0.0316(19) -0.0040(16) -0.0014(14) -0.0046(14) N22B 0.0338(15) 0.0373(18) 0.0366(17) 0.0042(14) 0.0038(12) -0.0028(11) C23B 0.0360(18) 0.044(2) 0.039(2) 0.0048(18) -0.0025(14) -0.0017(16) C24B 0.042(2) 0.037(2) 0.038(2) 0.0076(17) -0.0008(15) -0.0042(15) C25B 0.0361(19) 0.040(2) 0.042(2) 0.0019(18) -0.0013(15) 0.0017(15) C26B 0.0335(17) 0.035(2) 0.037(2) -0.0019(16) -0.0003(14) -0.0005(14) _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 O1A C1A 1.231(4) . ? C1A N1A 1.346(4) . ? C1A C21A 1.508(4) . ? N1A C11A 1.412(4) . ? N1A H1A 1.00(3) . ? C11A C12A 1.391(4) . ? C11A C16A 1.394(4) . ? C12A C13A 1.378(5) . ? C12A H12A 0.9500 . ? C13A C14A 1.370(4) . ? C13A H13A 0.9500 . ? C14A C15A 1.383(5) . ? C14A H14A 0.9500 . ? C15A C16A 1.385(5) . ? C15A H15A 0.9500 . ? C16A H16A 0.9500 . ? C21A N22A 1.347(4) . ? C21A C26A 1.377(4) . ? N22A C23A 1.339(4) . ? C23A C24A 1.379(5) . ? C23A H23A 0.9500 . ? C24A C25A 1.366(4) . ? C24A H24A 0.9500 . ? C25A C26A 1.383(5) . ? C25A H25A 0.9500 . ? C26A H26A 0.9500 . ? F13B C13B 1.364(4) . ? O1B C1B 1.228(4) . ? C1B N1B 1.351(4) . ? C1B C21B 1.501(5) . ? N1B C11B 1.416(4) . ? N1B H1B 0.98(3) . ? C11B C16B 1.387(4) . ? C11B C12B 1.388(4) . ? C12B C13B 1.378(5) . ? C12B H12B 0.9500 . ? C13B C14B 1.362(5) . ? C14B C15B 1.379(5) . ? C14B H14B 0.9500 . ? C15B C16B 1.376(5) . ? C15B H15B 0.9500 . ? C16B H16B 0.9500 . ? C21B N22B 1.343(4) . ? C21B C26B 1.382(4) . ? N22B C23B 1.342(4) . ? C23B C24B 1.384(4) . ? C23B H23B 0.9500 . ? C24B C25B 1.376(4) . ? C24B H24B 0.9500 . ? C25B C26B 1.379(5) . ? C25B H25B 0.9500 . ? C26B H26B 0.9500 . ? 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 O1A C1A N1A 124.9(3) . . ? O1A C1A C21A 120.4(3) . . ? N1A C1A C21A 114.6(3) . . ? C1A N1A C11A 128.0(3) . . ? C1A N1A H1A 116.3(19) . . ? C11A N1A H1A 115.6(19) . . ? C12A C11A C16A 119.5(3) . . ? C12A C11A N1A 122.8(3) . . ? C16A C11A N1A 117.7(3) . . ? C13A C12A C11A 117.9(3) . . ? C13A C12A H12A 121.0 . . ? C11A C12A H12A 121.0 . . ? C14A C13A C12A 124.3(3) . . ? C14A C13A H13A 117.9 . . ? C12A C13A H13A 117.9 . . ? C13A C14A C15A 116.8(3) . . ? C13A C14A H14A 121.6 . . ? C15A C14A H14A 121.6 . . ? C14A C15A C16A 121.4(3) . . ? C14A C15A H15A 119.3 . . ? C16A C15A H15A 119.3 . . ? C15A C16A C11A 120.0(3) . . ? C15A C16A H16A 120.0 . . ? C11A C16A H16A 120.0 . . ? N22A C21A C26A 123.5(3) . . ? N22A C21A C1A 116.7(3) . . ? C26A C21A C1A 119.8(3) . . ? C23A N22A C21A 116.3(3) . . ? N22A C23A C24A 123.8(3) . . ? N22A C23A H23A 118.1 . . ? C24A C23A H23A 118.1 . . ? C25A C24A C23A 118.8(3) . . ? C25A C24A H24A 120.6 . . ? C23A C24A H24A 120.6 . . ? C24A C25A C26A 119.1(3) . . ? C24A C25A H25A 120.5 . . ? C26A C25A H25A 120.5 . . ? C21A C26A C25A 118.5(3) . . ? C21A C26A H26A 120.7 . . ? C25A C26A H26A 120.7 . . ? O1B C1B N1B 125.1(3) . . ? O1B C1B C21B 120.8(3) . . ? N1B C1B C21B 114.1(3) . . ? C1B N1B C11B 129.1(3) . . ? C1B N1B H1B 111.8(18) . . ? C11B N1B H1B 118.5(18) . . ? C16B C11B C12B 119.9(3) . . ? C16B C11B N1B 117.4(3) . . ? C12B C11B N1B 122.7(3) . . ? C13B C12B C11B 117.1(3) . . ? C13B C12B H12B 121.4 . . ? C11B C12B H12B 121.4 . . ? C14B C13B F13B 118.8(3) . . ? C14B C13B C12B 124.5(3) . . ? F13B C13B C12B 116.7(3) . . ? C13B C14B C15B 117.3(3) . . ? C13B C14B H14B 121.4 . . ? C15B C14B H14B 121.4 . . ? C16B C15B C14B 120.8(3) . . ? C16B C15B H15B 119.6 . . ? C14B C15B H15B 119.6 . . ? C15B C16B C11B 120.4(3) . . ? C15B C16B H16B 119.8 . . ? C11B C16B H16B 119.8 . . ? N22B C21B C26B 123.7(3) . . ? N22B C21B C1B 116.5(3) . . ? C26B C21B C1B 119.8(3) . . ? C23B N22B C21B 116.7(3) . . ? N22B C23B C24B 123.2(3) . . ? N22B C23B H23B 118.4 . . ? C24B C23B H23B 118.4 . . ? C25B C24B C23B 118.9(3) . . ? C25B C24B H24B 120.6 . . ? C23B C24B H24B 120.6 . . ? C24B C25B C26B 119.0(3) . . ? C24B C25B H25B 120.5 . . ? C26B C25B H25B 120.5 . . ? C25B C26B C21B 118.5(3) . . ? C25B C26B H26B 120.8 . . ? C21B C26B H26B 120.8 . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag O1A C1A N1A C11A -2.7(5) . . . . ? C21A C1A N1A C11A 176.8(3) . . . . ? C1A N1A C11A C12A -3.5(5) . . . . ? C1A N1A C11A C16A 177.6(3) . . . . ? C16A C11A C12A C13A -0.8(5) . . . . ? N1A C11A C12A C13A -179.7(3) . . . . ? C11A C12A C13A C14A -0.1(5) . . . . ? C12A C13A C14A C15A 0.4(5) . . . . ? C13A C14A C15A C16A 0.3(5) . . . . ? C14A C15A C16A C11A -1.2(5) . . . . ? C12A C11A C16A C15A 1.4(5) . . . . ? N1A C11A C16A C15A -179.6(3) . . . . ? O1A C1A C21A N22A -179.4(3) . . . . ? N1A C1A C21A N22A 1.1(4) . . . . ? O1A C1A C21A C26A 1.1(5) . . . . ? N1A C1A C21A C26A -178.4(3) . . . . ? C26A C21A N22A C23A -1.4(5) . . . . ? C1A C21A N22A C23A 179.2(3) . . . . ? C21A N22A C23A C24A 1.0(5) . . . . ? N22A C23A C24A C25A 0.1(5) . . . . ? C23A C24A C25A C26A -0.9(5) . . . . ? N22A C21A C26A C25A 0.7(5) . . . . ? C1A C21A C26A C25A -179.9(3) . . . . ? C24A C25A C26A C21A 0.5(5) . . . . ? O1B C1B N1B C11B 2.9(5) . . . . ? C21B C1B N1B C11B -177.8(3) . . . . ? C1B N1B C11B C16B 172.0(3) . . . . ? C1B N1B C11B C12B -8.6(5) . . . . ? C16B C11B C12B C13B 0.4(5) . . . . ? N1B C11B C12B C13B -179.0(3) . . . . ? C11B C12B C13B C14B -0.4(5) . . . . ? C11B C12B C13B F13B 178.5(3) . . . . ? F13B C13B C14B C15B -179.0(3) . . . . ? C12B C13B C14B C15B 0.0(5) . . . . ? C13B C14B C15B C16B 0.5(5) . . . . ? C14B C15B C16B C11B -0.6(5) . . . . ? C12B C11B C16B C15B 0.1(5) . . . . ? N1B C11B C16B C15B 179.6(3) . . . . ? O1B C1B C21B N22B -175.5(3) . . . . ? N1B C1B C21B N22B 5.1(4) . . . . ? O1B C1B C21B C26B 3.0(5) . . . . ? N1B C1B C21B C26B -176.4(3) . . . . ? C26B C21B N22B C23B -0.1(5) . . . . ? C1B C21B N22B C23B 178.3(3) . . . . ? C21B N22B C23B C24B 0.1(5) . . . . ? N22B C23B C24B C25B 0.3(5) . . . . ? C23B C24B C25B C26B -0.6(5) . . . . ? C24B C25B C26B C21B 0.5(5) . . . . ? N22B C21B C26B C25B -0.2(5) . . . . ? C1B C21B C26B C25B -178.6(3) . . . . ? loop_ _geom_hbond_atom_site_label_D _geom_hbond_atom_site_label_H _geom_hbond_atom_site_label_A _geom_hbond_distance_DH _geom_hbond_distance_HA _geom_hbond_distance_DA _geom_hbond_angle_DHA _geom_hbond_site_symmetry_A _geom_hbond_publ_flag # # Hydrogen bonding scheme # ======== ======= ====== # # D H A D-H H...A D...A D-H...A symm publ # - - - --- ----- ----- ------- ---- ---- N1A H1A N22A 1.00(3) 2.20(3) 2.675(4) 108(2) . yes N1B H1B N22B 0.98(3) 2.11(3) 2.655(4) 113(2) . yes C12A H12A O1A 0.95 2.23 2.845(4) 122 . yes C12B H12B O1B 0.95 2.29 2.895(4) 121 . yes C16A H16A O1B 0.95 2.49 3.362(4) 152 . yes