data_14srv258 _audit_creation_date 2014-11-24 _audit_creation_method ; Olex2 1.2-beta (compiled 2014.11.21 svn.r3092 for OlexSys, GUI svn.r4949) ; _publ_contact_author_address ; Science site South Rd Durham ; _publ_contact_author_email d.s.yufit@durham.ac.uk _publ_contact_author_name 'Yufit, D.S.' _publ_contact_author_phone '' _publ_section_references ; Dolomanov, O.V., Bourhis, L.J., Gildea, R.J, Howard, J.A.K. & Puschmann, H. (2009), J. Appl. Cryst. 42, 339-341. Sheldrick, G.M. (2008). Acta Cryst. A64, 112-122. ; _chemical_name_common ? _chemical_name_systematic ; ? ; _chemical_formula_moiety 'C7 H10 F N O3' _chemical_formula_sum 'C7 H10 F N O3' _chemical_formula_weight 175.16 _chemical_absolute_configuration ad _chemical_melting_point ? loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source 'C' 'C' 0.0181 0.0091 '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' 'F' 'F' 0.0727 0.0534 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 'N' 'N' 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 'O' 'O' 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _space_group_crystal_system 'monoclinic' _space_group_IT_number 4 _space_group_name_H-M_alt 'P 1 21 1' _space_group_name_Hall 'P 2yb' loop_ _space_group_symop_id _space_group_symop_operation_xyz 1 'x, y, z' 2 '-x, y+1/2, -z' _cell_length_a 8.5211(3) _cell_length_b 10.3039(3) _cell_length_c 9.1547(3) _cell_angle_alpha 90.00 _cell_angle_beta 90.3650(8) _cell_angle_gamma 90.00 _cell_volume 803.77(5) _cell_formula_units_Z 4 _cell_measurement_reflns_used 7543 _cell_measurement_temperature 120.0(2) _cell_measurement_theta_max 74.36 _cell_measurement_theta_min 4.29 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_calc_flag _atom_site_disorder_assembly _atom_site_disorder_group _atom_site_refinement_flags_posn F1 F 0.74634(17) 0.54728(15) 0.13756(16) 0.0368(4) Uani 1 d . . . O1 O 0.6903(2) 0.29830(19) 0.2600(2) 0.0373(4) Uani 1 d . . . O2 O 0.80105(19) 0.27347(17) -0.08541(19) 0.0311(4) Uani 1 d . . . O3 O 0.9704(2) 0.3938(3) 0.0451(3) 0.0528(6) Uani 1 d . . . N1 N 0.4532(3) 0.3510(2) 0.1621(2) 0.0358(5) Uani 1 d . . . C1 C 0.6094(3) 0.3546(2) 0.1680(2) 0.0286(5) Uani 1 d . . . C2 C 0.6929(3) 0.4414(2) 0.0549(3) 0.0290(5) Uani 1 d . . . C3 C 0.5934(3) 0.4920(3) -0.0694(3) 0.0346(6) Uani 1 d . . . C4 C 0.4317(3) 0.5305(3) -0.0134(3) 0.0379(6) Uani 1 d . . . C5 C 0.3524(3) 0.4125(3) 0.0507(3) 0.0440(7) Uani 1 d . . . C6 C 0.8403(3) 0.3682(2) 0.0053(3) 0.0299(5) Uani 1 d . . . C7 C 0.9305(3) 0.1902(3) -0.1316(3) 0.0396(6) Uani 1 d . . . H1 H 0.411(4) 0.319(4) 0.234(4) 0.036(8) Uiso 1 d . . . H3A H 0.582(5) 0.432(4) -0.137(4) 0.052(10) Uiso 1 d . . . H3B H 0.650(5) 0.563(4) -0.117(4) 0.051(10) Uiso 1 d . . . H4A H 0.444(4) 0.599(3) 0.055(4) 0.031(7) Uiso 1 d . . . H4B H 0.371(3) 0.560(3) -0.097(3) 0.019(6) Uiso 1 d . . . H5A H 0.263(4) 0.444(4) 0.098(4) 0.038(8) Uiso 1 d . . . H5B H 0.321(4) 0.344(4) -0.037(4) 0.046(9) Uiso 1 d . . . H7A H 0.874(4) 0.137(3) -0.217(4) 0.035(8) Uiso 1 d . . . H7B H 0.961(5) 0.139(5) -0.055(5) 0.056(11) Uiso 1 d . . . H7C H 1.001(5) 0.244(4) -0.177(4) 0.047(9) Uiso 1 d . . . F11 F 0.21984(18) 0.36622(16) 0.67839(16) 0.0375(4) Uani 1 d . . . O11 O 0.2110(2) 0.32427(19) 0.3745(2) 0.0360(4) Uani 1 d . . . O12 O 0.3261(2) 0.61490(19) 0.43529(19) 0.0342(4) Uani 1 d . . . O13 O 0.4675(2) 0.50597(19) 0.6046(2) 0.0355(4) Uani 1 d . . . N11 N -0.0241(2) 0.4225(2) 0.4037(2) 0.0338(5) Uani 1 d . . . C11 C 0.1242(3) 0.3988(2) 0.4416(3) 0.0298(5) Uani 1 d . . . C12 C 0.1891(3) 0.4664(2) 0.5796(3) 0.0289(5) Uani 1 d . . . C13 C 0.0769(3) 0.5633(3) 0.6508(3) 0.0354(5) Uani 1 d . . . C14 C -0.0918(3) 0.5154(3) 0.6408(3) 0.0354(5) Uani 1 d . . . C15 C -0.1381(3) 0.5033(3) 0.4817(3) 0.0361(6) Uani 1 d . . . C16 C 0.3466(3) 0.5293(2) 0.5431(2) 0.0297(5) Uani 1 d . . . C17 C 0.4646(3) 0.6888(3) 0.3979(3) 0.0391(6) Uani 1 d . . . H11 H -0.057(4) 0.396(4) 0.329(4) 0.045(9) Uiso 1 d . . . H13A H 0.095(4) 0.647(4) 0.600(4) 0.036(8) Uiso 1 d . . . H13B H 0.104(5) 0.584(4) 0.749(5) 0.057(11) Uiso 1 d . . . H14A H -0.170(4) 0.576(4) 0.692(4) 0.040(8) Uiso 1 d . . . H14B H -0.101(4) 0.433(4) 0.687(4) 0.038(8) Uiso 1 d . . . H15A H -0.141(3) 0.591(3) 0.438(3) 0.019(6) Uiso 1 d . . . H15B H -0.231(4) 0.461(4) 0.473(4) 0.037(8) Uiso 1 d . . . H17A H 0.422(4) 0.742(5) 0.328(4) 0.050(10) Uiso 1 d . . . H17B H 0.544(6) 0.625(6) 0.345(6) 0.083(15) Uiso 1 d . . . H17C H 0.502(4) 0.726(4) 0.472(4) 0.039(9) Uiso 1 d . . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 F1 0.0366(8) 0.0332(8) 0.0406(8) -0.0089(6) 0.0044(6) -0.0034(6) O1 0.0364(9) 0.0395(10) 0.0359(9) 0.0050(8) -0.0047(7) 0.0011(8) O2 0.0261(8) 0.0285(8) 0.0388(9) -0.0028(7) 0.0027(6) 0.0022(7) O3 0.0252(9) 0.0621(14) 0.0711(15) -0.0277(12) -0.0060(8) 0.0026(9) N1 0.0280(10) 0.0436(12) 0.0358(11) 0.0039(10) 0.0019(8) -0.0002(9) C1 0.0293(11) 0.0297(11) 0.0269(10) -0.0024(9) -0.0018(8) 0.0014(9) C2 0.0267(11) 0.0295(11) 0.0308(11) -0.0014(9) -0.0001(8) 0.0012(10) C3 0.0338(13) 0.0390(14) 0.0308(12) 0.0008(11) 0.0014(10) 0.0104(10) C4 0.0347(13) 0.0437(14) 0.0352(12) 0.0006(12) -0.0027(10) 0.0125(11) C5 0.0224(11) 0.0600(19) 0.0495(15) 0.0010(14) -0.0063(10) 0.0030(12) C6 0.0216(10) 0.0325(11) 0.0356(11) 0.0019(10) 0.0010(8) -0.0004(9) C7 0.0346(13) 0.0344(13) 0.0499(15) -0.0038(13) 0.0077(11) 0.0074(11) F11 0.0376(7) 0.0408(8) 0.0342(7) 0.0103(6) -0.0012(6) -0.0015(6) O11 0.0339(9) 0.0364(9) 0.0379(9) -0.0046(7) 0.0045(7) 0.0015(7) O12 0.0317(9) 0.0370(9) 0.0339(9) 0.0067(7) -0.0033(7) -0.0045(7) O13 0.0292(9) 0.0400(10) 0.0374(9) 0.0042(8) -0.0028(7) -0.0013(7) N11 0.0304(10) 0.0371(12) 0.0338(11) -0.0030(9) -0.0052(8) 0.0009(9) C11 0.0300(11) 0.0279(11) 0.0315(11) 0.0016(9) 0.0018(9) -0.0039(9) C12 0.0285(12) 0.0295(12) 0.0286(11) 0.0026(9) -0.0023(8) 0.0005(9) C13 0.0319(12) 0.0406(14) 0.0338(12) -0.0069(11) 0.0017(9) -0.0010(10) C14 0.0307(12) 0.0391(14) 0.0365(12) 0.0032(11) 0.0041(9) 0.0038(10) C15 0.0295(12) 0.0396(14) 0.0393(13) 0.0003(11) -0.0030(9) 0.0030(11) C16 0.0310(11) 0.0294(11) 0.0287(10) -0.0024(9) -0.0026(8) -0.0013(9) C17 0.0398(14) 0.0385(14) 0.0391(14) 0.0063(12) -0.0015(11) -0.0119(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 F1 C2 1.402(3) . ? O1 C1 1.230(3) . ? O2 C6 1.323(3) . ? O2 C7 1.462(3) . ? O3 C6 1.195(3) . ? N1 C1 1.332(3) . ? N1 C5 1.472(4) . ? N1 H1 0.82(4) . ? C1 C2 1.545(3) . ? C2 C3 1.507(3) . ? C2 C6 1.536(3) . ? C3 C4 1.525(4) . ? C3 H3A 0.88(4) . ? C3 H3B 0.98(4) . ? C4 C5 1.512(4) . ? C4 H4A 0.95(4) . ? C4 H4B 0.97(3) . ? C5 H5A 0.94(4) . ? C5 H5B 1.10(4) . ? C7 H7A 1.07(3) . ? C7 H7B 0.91(4) . ? C7 H7C 0.91(4) . ? F11 C12 1.396(3) . ? O11 C11 1.234(3) . ? O12 C16 1.334(3) . ? O12 C17 1.447(3) . ? O13 C16 1.195(3) . ? N11 C11 1.331(3) . ? N11 C15 1.468(3) . ? N11 H11 0.79(4) . ? C11 C12 1.542(3) . ? C12 C13 1.530(3) . ? C12 C16 1.529(3) . ? C13 C14 1.522(4) . ? C13 H13A 0.99(4) . ? C13 H13B 0.95(4) . ? C14 C15 1.512(4) . ? C14 H14A 1.03(4) . ? C14 H14B 0.95(4) . ? C15 H15A 0.99(3) . ? C15 H15B 0.91(4) . ? C17 H17A 0.92(4) . ? C17 H17B 1.06(6) . ? C17 H17C 0.84(4) . ? 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 C6 O2 C7 115.23(19) . . ? C1 N1 C5 126.5(2) . . ? C1 N1 H1 115(2) . . ? C5 N1 H1 118(2) . . ? O1 C1 N1 124.8(2) . . ? O1 C1 C2 118.3(2) . . ? N1 C1 C2 116.9(2) . . ? F1 C2 C1 103.74(18) . . ? F1 C2 C3 108.5(2) . . ? F1 C2 C6 106.14(18) . . ? C3 C2 C1 116.5(2) . . ? C3 C2 C6 113.84(19) . . ? C6 C2 C1 107.14(19) . . ? C2 C3 C4 109.9(2) . . ? C2 C3 H3A 110(3) . . ? C2 C3 H3B 109(2) . . ? C4 C3 H3A 109(3) . . ? C4 C3 H3B 114(2) . . ? H3A C3 H3B 105(3) . . ? C3 C4 H4A 108.7(19) . . ? C3 C4 H4B 106.9(16) . . ? C5 C4 C3 109.2(2) . . ? C5 C4 H4A 113(2) . . ? C5 C4 H4B 108.7(17) . . ? H4A C4 H4B 110(3) . . ? N1 C5 C4 110.7(2) . . ? N1 C5 H5A 108(2) . . ? N1 C5 H5B 112(2) . . ? C4 C5 H5A 105(2) . . ? C4 C5 H5B 110(2) . . ? H5A C5 H5B 111(3) . . ? O2 C6 C2 110.10(19) . . ? O3 C6 O2 125.8(2) . . ? O3 C6 C2 124.1(2) . . ? O2 C7 H7A 100.1(18) . . ? O2 C7 H7B 109(3) . . ? O2 C7 H7C 106(3) . . ? H7A C7 H7B 113(3) . . ? H7A C7 H7C 106(3) . . ? H7B C7 H7C 121(3) . . ? C16 O12 C17 114.81(19) . . ? C11 N11 C15 127.4(2) . . ? C11 N11 H11 120(3) . . ? C15 N11 H11 113(3) . . ? O11 C11 N11 123.7(2) . . ? O11 C11 C12 118.5(2) . . ? N11 C11 C12 117.8(2) . . ? F11 C12 C11 105.15(19) . . ? F11 C12 C13 108.76(19) . . ? F11 C12 C16 107.08(18) . . ? C13 C12 C11 114.9(2) . . ? C16 C12 C11 108.84(19) . . ? C16 C12 C13 111.6(2) . . ? C12 C13 H13A 106(2) . . ? C12 C13 H13B 113(3) . . ? C14 C13 C12 110.8(2) . . ? C14 C13 H13A 113.6(19) . . ? C14 C13 H13B 111(3) . . ? H13A C13 H13B 102(3) . . ? C13 C14 H14A 113(2) . . ? C13 C14 H14B 110(2) . . ? C15 C14 C13 109.0(2) . . ? C15 C14 H14A 108.7(19) . . ? C15 C14 H14B 110(2) . . ? H14A C14 H14B 107(3) . . ? N11 C15 C14 110.3(2) . . ? N11 C15 H15A 109.5(17) . . ? N11 C15 H15B 106(2) . . ? C14 C15 H15A 108.7(16) . . ? C14 C15 H15B 110(2) . . ? H15A C15 H15B 112(3) . . ? O12 C16 C12 109.32(19) . . ? O13 C16 O12 126.1(2) . . ? O13 C16 C12 124.5(2) . . ? O12 C17 H17A 99(2) . . ? O12 C17 H17B 108(3) . . ? O12 C17 H17C 110(3) . . ? H17A C17 H17B 108(4) . . ? H17A C17 H17C 116(4) . . ? H17B C17 H17C 115(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 N1 H1 O11 0.82(4) 2.14(4) 2.858(3) 145(3) . N11 H11 O1 0.79(4) 2.46(4) 3.042(3) 132(3) 1_455 loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag F1 C2 C3 C4 -77.0(3) . . . . ? F1 C2 C6 O2 -174.02(19) . . . . ? F1 C2 C6 O3 6.6(3) . . . . ? O1 C1 C2 F1 -69.9(3) . . . . ? O1 C1 C2 C3 170.9(2) . . . . ? O1 C1 C2 C6 42.1(3) . . . . ? N1 C1 C2 F1 107.3(2) . . . . ? N1 C1 C2 C3 -11.9(3) . . . . ? N1 C1 C2 C6 -140.7(2) . . . . ? C1 N1 C5 C4 -27.6(4) . . . . ? C1 C2 C3 C4 39.6(3) . . . . ? C1 C2 C6 O2 75.6(2) . . . . ? C1 C2 C6 O3 -103.8(3) . . . . ? C2 C3 C4 C5 -60.9(3) . . . . ? C3 C2 C6 O2 -54.7(3) . . . . ? C3 C2 C6 O3 125.9(3) . . . . ? C3 C4 C5 N1 54.0(3) . . . . ? C5 N1 C1 O1 -177.3(3) . . . . ? C5 N1 C1 C2 5.7(4) . . . . ? C6 C2 C3 C4 165.1(2) . . . . ? C7 O2 C6 O3 3.9(4) . . . . ? C7 O2 C6 C2 -175.51(19) . . . . ? F11 C12 C13 C14 -80.8(2) . . . . ? F11 C12 C16 O12 172.25(19) . . . . ? F11 C12 C16 O13 -9.0(3) . . . . ? O11 C11 C12 F11 -63.9(3) . . . . ? O11 C11 C12 C13 176.5(2) . . . . ? O11 C11 C12 C16 50.5(3) . . . . ? N11 C11 C12 F11 114.7(2) . . . . ? N11 C11 C12 C13 -4.9(3) . . . . ? N11 C11 C12 C16 -130.9(2) . . . . ? C11 N11 C15 C14 -22.7(4) . . . . ? C11 C12 C13 C14 36.7(3) . . . . ? C11 C12 C16 O12 59.1(3) . . . . ? C11 C12 C16 O13 -122.2(3) . . . . ? C12 C13 C14 C15 -61.7(3) . . . . ? C13 C12 C16 O12 -68.8(2) . . . . ? C13 C12 C16 O13 109.9(3) . . . . ? C13 C14 C15 N11 53.6(3) . . . . ? C15 N11 C11 O11 176.1(2) . . . . ? C15 N11 C11 C12 -2.4(4) . . . . ? C16 C12 C13 C14 161.3(2) . . . . ? C17 O12 C16 O13 -3.3(4) . . . . ? C17 O12 C16 C12 175.4(2) . . . . ? _olex2_submission_special_instructions 'No special instructions were received'