data_15srv201 _audit_creation_date 2015-07-22 _audit_creation_method ; Olex2 1.2-beta (compiled 2015.01.26 svn.r3150 for OlexSys, GUI svn.r4998) ; _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 'C11 H12 F N O3' _chemical_formula_sum 'C11 H12 F N O3' _chemical_formula_weight 225.22 _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' 0.0033 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' 'F' 'F' 0.0171 0.0103 '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' _space_group_crystal_system 'orthorhombic' _space_group_IT_number 61 _space_group_name_H-M_alt 'P b c a' _space_group_name_Hall '-P 2ac 2ab' loop_ _space_group_symop_id _space_group_symop_operation_xyz 1 'x, y, z' 2 '-x+1/2, -y, z+1/2' 3 'x+1/2, -y+1/2, -z' 4 '-x, y+1/2, -z+1/2' 5 '-x, -y, -z' 6 'x-1/2, y, -z-1/2' 7 '-x-1/2, y-1/2, z' 8 'x, -y-1/2, z-1/2' _cell_length_a 8.5328(6) _cell_length_b 10.3079(8) _cell_length_c 23.8695(18) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 2099.4(3) _cell_formula_units_Z 8 _cell_measurement_reflns_used 4529 _cell_measurement_temperature 120.0 _cell_measurement_theta_max 27.72 _cell_measurement_theta_min 2.93 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 0.16681(12) 0.10469(10) 0.43571(4) 0.0309(3) Uani 1 d . . . O1 O 0.07033(13) 0.33051(12) 0.48096(5) 0.0286(3) Uani 1 d . . . O2 O 0.41156(14) 0.34685(12) 0.38175(5) 0.0270(3) Uani 1 d . . . O3 O 0.19027(14) 0.25986(13) 0.34664(5) 0.0317(3) Uani 1 d . . . N1 N 0.31445(17) 0.35571(14) 0.51665(6) 0.0240(3) Uani 1 d . . . C1 C 0.21097(18) 0.30267(16) 0.48232(6) 0.0225(3) Uani 1 d . . . C2 C 0.27461(19) 0.20448(16) 0.43993(6) 0.0233(3) Uani 1 d . . . C3 C 0.28570(18) 0.27161(15) 0.38326(6) 0.0229(3) Uani 1 d . . . C4 C 0.4282(2) 0.42626(19) 0.33180(7) 0.0315(4) Uani 1 d . . . C5 C 0.2708(2) 0.46238(17) 0.55389(7) 0.0260(3) Uani 1 d . . . C6 C 0.20976(18) 0.41923(15) 0.61027(6) 0.0230(3) Uani 1 d . . . C7 C 0.2856(2) 0.32325(17) 0.64093(7) 0.0281(3) Uani 1 d . . . C8 C 0.2337(2) 0.29153(19) 0.69439(8) 0.0331(4) Uani 1 d . . . C9 C 0.1068(2) 0.35531(19) 0.71770(7) 0.0330(4) Uani 1 d . . . C10 C 0.0300(2) 0.45013(19) 0.68727(7) 0.0321(4) Uani 1 d . . . C11 C 0.0810(2) 0.48187(16) 0.63355(7) 0.0264(3) Uani 1 d . . . H1 H 0.407(3) 0.323(2) 0.5176(9) 0.038(6) Uiso 1 d . . . H2 H 0.374(2) 0.1691(19) 0.4500(8) 0.023(5) Uiso 1 d . . . H4A H 0.410(3) 0.375(2) 0.2999(10) 0.036(6) Uiso 1 d . . . H4B H 0.536(3) 0.459(3) 0.3319(10) 0.054(7) Uiso 1 d . . . H4C H 0.354(3) 0.494(3) 0.3318(10) 0.049(7) Uiso 1 d . . . H5A H 0.364(2) 0.514(2) 0.5592(8) 0.030(5) Uiso 1 d . . . H5B H 0.189(2) 0.517(2) 0.5345(9) 0.031(5) Uiso 1 d . . . H7 H 0.375(3) 0.278(2) 0.6246(9) 0.038(6) Uiso 1 d . . . H8 H 0.292(3) 0.224(3) 0.7149(10) 0.049(7) Uiso 1 d . . . H9 H 0.072(3) 0.333(2) 0.7544(10) 0.041(6) Uiso 1 d . . . H10 H -0.061(3) 0.495(2) 0.7033(9) 0.036(6) Uiso 1 d . . . H11 H 0.025(2) 0.551(2) 0.6119(9) 0.036(6) 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 0.0375(6) 0.0249(5) 0.0303(5) -0.0001(4) -0.0018(4) -0.0081(4) O1 0.0211(5) 0.0340(7) 0.0307(6) -0.0019(5) -0.0002(4) 0.0001(5) O2 0.0279(6) 0.0296(6) 0.0235(6) 0.0008(4) -0.0005(4) -0.0046(5) O3 0.0318(6) 0.0389(7) 0.0245(6) 0.0019(5) -0.0049(5) -0.0043(5) N1 0.0222(7) 0.0265(7) 0.0234(6) -0.0035(5) -0.0004(5) 0.0005(5) C1 0.0237(7) 0.0238(7) 0.0199(7) 0.0011(6) 0.0013(5) -0.0016(6) C2 0.0245(7) 0.0221(7) 0.0232(7) -0.0003(6) -0.0010(6) -0.0021(6) C3 0.0234(7) 0.0229(7) 0.0224(7) -0.0030(6) 0.0012(6) 0.0008(6) C4 0.0408(10) 0.0289(9) 0.0248(8) 0.0013(7) 0.0039(7) -0.0027(8) C5 0.0296(8) 0.0243(8) 0.0239(7) -0.0014(6) 0.0013(6) -0.0016(6) C6 0.0245(7) 0.0225(7) 0.0220(7) -0.0018(5) -0.0018(6) -0.0027(6) C7 0.0250(8) 0.0281(9) 0.0311(8) 0.0020(7) -0.0018(6) 0.0015(6) C8 0.0360(9) 0.0333(9) 0.0299(8) 0.0068(7) -0.0080(7) -0.0028(7) C9 0.0386(10) 0.0387(10) 0.0219(8) -0.0001(7) -0.0003(7) -0.0075(8) C10 0.0335(9) 0.0345(9) 0.0282(8) -0.0057(7) 0.0040(7) -0.0008(7) C11 0.0279(8) 0.0244(8) 0.0268(8) -0.0028(6) -0.0010(6) 0.0014(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 F1 C2 1.3836(18) . ? O1 C1 1.2344(19) . ? O2 C3 1.3252(19) . ? O2 C4 1.453(2) . ? O3 C3 1.2007(19) . ? N1 C1 1.323(2) . ? N1 C5 1.462(2) . ? N1 H1 0.86(2) . ? C1 C2 1.531(2) . ? C2 C3 1.522(2) . ? C2 H2 0.957(19) . ? C4 H4A 0.94(2) . ? C4 H4B 0.98(3) . ? C4 H4C 0.94(3) . ? C5 C6 1.510(2) . ? C5 H5A 0.97(2) . ? C5 H5B 1.01(2) . ? C6 C7 1.390(2) . ? C6 C11 1.390(2) . ? C7 C8 1.390(3) . ? C7 H7 0.97(2) . ? C8 C9 1.383(3) . ? C8 H8 0.98(3) . ? C9 C10 1.383(3) . ? C9 H9 0.95(2) . ? C10 C11 1.393(2) . ? C10 H10 0.98(2) . ? C11 H11 1.00(2) . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C3 O2 C4 115.55(13) . . ? C1 N1 C5 121.14(14) . . ? C1 N1 H1 117.7(15) . . ? C5 N1 H1 121.1(15) . . ? O1 C1 N1 124.70(15) . . ? O1 C1 C2 118.76(14) . . ? N1 C1 C2 116.48(14) . . ? F1 C2 C1 107.68(12) . . ? F1 C2 C3 108.33(12) . . ? F1 C2 H2 109.1(12) . . ? C1 C2 H2 113.6(12) . . ? C3 C2 C1 107.99(13) . . ? C3 C2 H2 110.0(12) . . ? O2 C3 C2 109.90(13) . . ? O3 C3 O2 126.08(15) . . ? O3 C3 C2 123.97(15) . . ? O2 C4 H4A 109.2(14) . . ? O2 C4 H4B 106.5(15) . . ? O2 C4 H4C 110.5(15) . . ? H4A C4 H4B 111(2) . . ? H4A C4 H4C 107.8(19) . . ? H4B C4 H4C 112(2) . . ? N1 C5 C6 114.09(14) . . ? N1 C5 H5A 106.4(12) . . ? N1 C5 H5B 108.6(12) . . ? C6 C5 H5A 109.3(12) . . ? C6 C5 H5B 109.5(12) . . ? H5A C5 H5B 108.9(17) . . ? C7 C6 C5 121.22(15) . . ? C7 C6 C11 119.21(15) . . ? C11 C6 C5 119.46(15) . . ? C6 C7 H7 119.5(13) . . ? C8 C7 C6 120.15(16) . . ? C8 C7 H7 120.3(13) . . ? C7 C8 H8 117.4(14) . . ? C9 C8 C7 120.46(17) . . ? C9 C8 H8 122.1(14) . . ? C8 C9 H9 120.0(13) . . ? C10 C9 C8 119.71(17) . . ? C10 C9 H9 120.3(13) . . ? C9 C10 C11 120.08(17) . . ? C9 C10 H10 120.3(13) . . ? C11 C10 H10 119.6(13) . . ? C6 C11 C10 120.38(16) . . ? C6 C11 H11 120.1(12) . . ? C10 C11 H11 119.5(12) . . ? 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 O1 0.86(2) 2.11(2) 2.9077(19) 155(2) 3_556 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 C2 F1 -41.90(19) . . . . ? O2 C3 C2 F1 -165.68(13) . . . . ? O3 C3 C2 F1 16.5(2) . . . . ? N1 C1 C2 F1 140.78(14) . . . . ? C1 C2 C3 O2 77.95(16) . . . . ? C1 C2 C3 O3 -99.84(18) . . . . ? C2 C1 N1 C5 172.14(14) . . . . ? C2 C3 O2 C4 -174.42(14) . . . . ? C3 C2 C1 O1 74.89(18) . . . . ? C3 C2 C1 N1 -102.43(16) . . . . ? C4 O2 C3 O3 3.3(2) . . . . ? C5 N1 C1 O1 -5.0(3) . . . . ? C6 C5 N1 C1 89.20(19) . . . . ? C7 C6 C5 N1 45.7(2) . . . . ? C11 C6 C5 N1 -138.24(16) . . . . ? _olex2_submission_special_instructions 'No special instructions were received'