data_16srv100 _audit_creation_date 2016-03-09 _audit_creation_method ; Olex2 1.2-beta (compiled 2016.02.19 svn.r3266 for OlexSys, GUI svn.r5155) ; loop_ _publ_author_name _publ_author_email _publ_author_address 'Yufit, D.' d.s.yufit@durham.ac.uk ; Science Site, South Rd. Durham DH1 3LE UK ; _publ_contact_author_address ? _publ_contact_author_email ? _publ_contact_author_name '' _publ_contact_author_phone ? _publ_section_references ; Bourhis, L.J., Dolomanov, O.V., Gildea, R.J., Howard, J.A.K., Puschmann, H. (2015). Acta Cryst. A71, 59-75. 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 H12 F N O4' _chemical_formula_sum 'C7 H12 F N O4' _chemical_formula_weight 193.18 _chemical_absolute_configuration unk _chemical_melting_point ? _chemical_oxdiff_formula 'C9 H17 Cl1 F1 N1 O4' 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 33 _space_group_name_H-M_alt 'P n a 21' _space_group_name_Hall 'P 2c -2n' loop_ _space_group_symop_id _space_group_symop_operation_xyz 1 'x, y, z' 2 '-x, -y, z+1/2' 3 '-x+1/2, y+1/2, z+1/2' 4 'x+1/2, -y+1/2, z' _cell_length_a 11.0907(3) _cell_length_b 8.2238(2) _cell_length_c 9.5589(3) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 871.85(4) _cell_formula_units_Z 4 _cell_measurement_reflns_used 4089 _cell_measurement_temperature 120.0 _cell_measurement_theta_max 32.5510 _cell_measurement_theta_min 3.0750 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 0.55614(7) 0.83378(10) 0.48296(8) 0.01531(18) Uani 1 d . . . O1 O 0.77251(9) 0.52920(12) 0.52671(11) 0.0154(2) Uani 1 d . . . O2 O 0.74489(10) 0.76557(13) 0.63786(12) 0.0184(2) Uani 1 d . . . O3 O 0.79807(10) 0.74281(13) 0.26226(11) 0.0201(2) Uani 1 d . . . O4 O 0.63871(9) 0.90955(12) 0.24013(11) 0.0177(2) Uani 1 d . . . H4 H 0.6759 0.9430 0.1692 0.027 Uiso 1 calc . . GR N1 N 0.42019(12) 0.07550(14) 0.30693(13) 0.0150(2) Uani 1 d . . . H1A H 0.3743 0.1150 0.2357 0.018 Uiso 1 calc . . GR H1B H 0.3714 0.0324 0.3739 0.018 Uiso 1 calc . . GR H1C H 0.4704 -0.0030 0.2736 0.018 Uiso 1 calc . . GR C1 C 0.63455(13) 0.71739(15) 0.42538(14) 0.0121(3) Uani 1 d . . . C2 C 0.72515(13) 0.66983(17) 0.54084(14) 0.0126(3) Uani 1 d . . . C3 C 0.70098(13) 0.79435(16) 0.30029(14) 0.0124(3) Uani 1 d . . . C4 C 0.55974(13) 0.57556(17) 0.37074(15) 0.0133(3) Uani 1 d . . . H4A H 0.6142 0.4969 0.3242 0.016 Uiso 1 calc . . R H4B H 0.5027 0.6168 0.2994 0.016 Uiso 1 calc . . R C5 C 0.48816(14) 0.48644(17) 0.48465(15) 0.0155(3) Uani 1 d . . . H5A H 0.4339 0.5644 0.5322 0.019 Uiso 1 calc . . R H5B H 0.5447 0.4424 0.5553 0.019 Uiso 1 calc . . R C6 C 0.41315(14) 0.34691(17) 0.42302(15) 0.0164(3) Uani 1 d . . . H6A H 0.3585 0.3035 0.4959 0.020 Uiso 1 calc . . R H6B H 0.3629 0.3890 0.3455 0.020 Uiso 1 calc . . R C7 C 0.49317(14) 0.21033(17) 0.36867(17) 0.0179(3) Uani 1 d . . . H7A H 0.5486 0.2540 0.2967 0.022 Uiso 1 calc . . R H7B H 0.5426 0.1672 0.4465 0.022 Uiso 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 F1 0.0161(4) 0.0133(4) 0.0165(4) 0.0003(3) 0.0022(3) 0.0046(3) O1 0.0185(5) 0.0145(4) 0.0132(4) 0.0011(4) -0.0018(4) 0.0043(4) O2 0.0185(5) 0.0200(5) 0.0167(5) -0.0044(4) -0.0027(4) 0.0017(4) O3 0.0165(5) 0.0223(5) 0.0214(5) 0.0056(4) 0.0050(4) 0.0048(4) O4 0.0173(5) 0.0181(5) 0.0179(5) 0.0090(4) 0.0054(4) 0.0039(4) N1 0.0163(6) 0.0122(5) 0.0165(5) 0.0016(5) 0.0012(5) -0.0003(4) C1 0.0126(7) 0.0110(6) 0.0127(6) 0.0007(5) 0.0013(5) 0.0025(5) C2 0.0116(6) 0.0142(6) 0.0120(6) 0.0029(5) 0.0018(5) -0.0011(5) C3 0.0147(7) 0.0112(5) 0.0114(6) 0.0014(5) -0.0008(5) -0.0021(5) C4 0.0136(7) 0.0134(6) 0.0129(6) 0.0016(5) 0.0002(5) -0.0007(5) C5 0.0181(7) 0.0152(6) 0.0132(6) -0.0001(5) 0.0016(6) -0.0033(5) C6 0.0161(7) 0.0135(6) 0.0196(7) 0.0001(5) 0.0032(5) -0.0018(5) C7 0.0141(7) 0.0143(6) 0.0254(7) -0.0012(6) 0.0011(6) -0.0021(5) _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 C1 1.4055(15) . ? O1 C2 1.2774(17) . ? O2 C2 1.2361(18) . ? O3 C3 1.2129(17) . ? O4 H4 0.8400 . ? O4 C3 1.3058(16) . ? N1 H1A 0.9100 . ? N1 H1B 0.9100 . ? N1 H1C 0.9100 . ? N1 C7 1.4942(18) . ? C1 C2 1.543(2) . ? C1 C3 1.5405(19) . ? C1 C4 1.5236(19) . ? C4 H4A 0.9900 . ? C4 H4B 0.9900 . ? C4 C5 1.534(2) . ? C5 H5A 0.9900 . ? C5 H5B 0.9900 . ? C5 C6 1.535(2) . ? C6 H6A 0.9900 . ? C6 H6B 0.9900 . ? C6 C7 1.523(2) . ? C7 H7A 0.9900 . ? C7 H7B 0.9900 . ? 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 O4 H4 109.5 . . ? H1A N1 H1B 109.5 . . ? H1A N1 H1C 109.5 . . ? H1B N1 H1C 109.5 . . ? C7 N1 H1A 109.5 . . ? C7 N1 H1B 109.5 . . ? C7 N1 H1C 109.5 . . ? F1 C1 C2 107.18(10) . . ? F1 C1 C3 108.67(10) . . ? F1 C1 C4 108.58(11) . . ? C3 C1 C2 110.36(11) . . ? C4 C1 C2 113.94(11) . . ? C4 C1 C3 107.99(11) . . ? O1 C2 C1 114.93(12) . . ? O2 C2 O1 125.68(13) . . ? O2 C2 C1 119.38(12) . . ? O3 C3 O4 126.23(13) . . ? O3 C3 C1 120.90(12) . . ? O4 C3 C1 112.77(12) . . ? C1 C4 H4A 108.8 . . ? C1 C4 H4B 108.8 . . ? C1 C4 C5 113.85(12) . . ? H4A C4 H4B 107.7 . . ? C5 C4 H4A 108.8 . . ? C5 C4 H4B 108.8 . . ? C4 C5 H5A 109.3 . . ? C4 C5 H5B 109.3 . . ? C4 C5 C6 111.42(12) . . ? H5A C5 H5B 108.0 . . ? C6 C5 H5A 109.3 . . ? C6 C5 H5B 109.3 . . ? C5 C6 H6A 109.3 . . ? C5 C6 H6B 109.3 . . ? H6A C6 H6B 108.0 . . ? C7 C6 C5 111.50(13) . . ? C7 C6 H6A 109.3 . . ? C7 C6 H6B 109.3 . . ? N1 C7 C6 111.49(12) . . ? N1 C7 H7A 109.3 . . ? N1 C7 H7B 109.3 . . ? C6 C7 H7A 109.3 . . ? C6 C7 H7B 109.3 . . ? H7A C7 H7B 108.0 . . ? 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 O4 H4 O1 0.84 1.64 2.4697(14) 169.8 3_654 N1 H1A O2 0.91 1.89 2.7699(17) 160.9 2_664 N1 H1B O1 0.91 1.90 2.7996(16) 171.9 4_455 N1 H1C O4 0.91 2.03 2.8538(17) 150.5 1_545 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 C1 C2 O1 155.43(11) . . . . ? F1 C1 C2 O2 -23.59(17) . . . . ? F1 C1 C3 O3 155.59(13) . . . . ? F1 C1 C3 O4 -27.80(15) . . . . ? F1 C1 C4 C5 -62.40(14) . . . . ? C1 C4 C5 C6 179.06(12) . . . . ? C2 C1 C3 O3 38.34(17) . . . . ? C2 C1 C3 O4 -145.06(12) . . . . ? C2 C1 C4 C5 56.95(16) . . . . ? C3 C1 C2 O1 -86.40(14) . . . . ? C3 C1 C2 O2 94.58(15) . . . . ? C3 C1 C4 C5 179.94(11) . . . . ? C4 C1 C2 O1 35.29(17) . . . . ? C4 C1 C2 O2 -143.74(14) . . . . ? C4 C1 C3 O3 -86.80(16) . . . . ? C4 C1 C3 O4 89.80(14) . . . . ? C4 C5 C6 C7 67.95(15) . . . . ? C5 C6 C7 N1 -179.24(12) . . . . ? loop_ _exptl_crystal_face_index_h _exptl_crystal_face_index_k _exptl_crystal_face_index_l _exptl_crystal_face_perp_dist _exptl_oxdiff_crystal_face_indexfrac_h _exptl_oxdiff_crystal_face_indexfrac_k _exptl_oxdiff_crystal_face_indexfrac_l _exptl_oxdiff_crystal_face_x _exptl_oxdiff_crystal_face_y _exptl_oxdiff_crystal_face_z 1 -2 -5 0.0390 1.0000 -2.0000 -5.0000 0.0815 -0.3703 -0.1672 -1 2 5 0.0390 -1.0000 2.0000 5.0000 -0.0815 0.3703 0.1672 5 0 3 0.1023 5.0000 0.0000 3.0000 0.0257 -0.0016 0.3887 -5 0 -3 0.1023 -5.0000 -0.0000 -3.0000 -0.0257 0.0016 -0.3887 -4 -5 3 0.1549 -4.0000 -5.0000 3.0000 -0.5456 -0.0326 -0.0468 4 5 -3 0.1549 4.0000 5.0000 -3.0000 0.5456 0.0326 0.0468 -5 -2 -1 0.1331 -5.0000 -2.0000 -1.0000 -0.2298 -0.0193 -0.2903 5 2 1 0.1331 5.0000 2.0000 1.0000 0.2298 0.0193 0.2903 -3 -5 -1 0.1245 -3.0000 -5.0000 -1.0000 -0.3707 -0.2442 -0.1769 _iucr_refine_instructions_details ; TITL 16srv100 CELL 0.71073 11.090733 8.223778 9.558937 90 90 90 ZERR 4 0.000349 0.000205 0.000263 0 0 0 LATT -1 SYMM -X,-Y,0.5+Z SYMM 0.5-X,0.5+Y,0.5+Z SYMM 0.5+X,0.5-Y,+Z SFAC C H F N O UNIT 28 48 4 4 16 EQIV $1 1.5-X,0.5+Y,-0.5+Z EQIV $2 1-X,1-Y,-0.5+Z EQIV $3 -0.5+X,0.5-Y,+Z EQIV $4 +X,-1+Y,+Z L.S. 9 PLAN 5 SIZE 0.08 0.25 0.37 TEMP -153.15 HTAB O4 O1_$1 HTAB N1 O2_$2 HTAB N1 O1_$3 HTAB N1 O4_$4 CONF BOND $h fmap 2 acta OMIT -2 60 OMIT 2 0 0 OMIT 14 5 -1 WGHT 0.04 0.1 FVAR 8.29199 REM REM REM F1 3 0.55614 0.83378 0.48296 11.00000 0.01615 0.01329 0.01648 = 0.00027 0.00225 0.00458 O1 5 0.77251 0.52920 0.52671 11.00000 0.01847 0.01449 0.01320 = 0.00110 -0.00178 0.00427 O2 5 0.74489 0.76557 0.63786 11.00000 0.01848 0.01996 0.01668 = -0.00440 -0.00270 0.00166 O3 5 0.79807 0.74281 0.26226 11.00000 0.01650 0.02226 0.02144 = 0.00558 0.00503 0.00477 O4 5 0.63872 0.90955 0.24013 11.00000 0.01726 0.01806 0.01788 = 0.00903 0.00541 0.00391 AFIX 147 H4 2 0.67593 0.94304 0.16923 11.00000 -1.50000 AFIX 0 N1 4 0.42019 0.07551 0.30693 11.00000 0.01635 0.01223 0.01648 = 0.00160 0.00125 -0.00033 AFIX 137 H1A 2 0.37433 0.11502 0.23569 11.00000 -1.20000 H1B 2 0.37141 0.03239 0.37390 11.00000 -1.20000 H1C 2 0.47038 -0.00300 0.27362 11.00000 -1.20000 AFIX 0 C1 1 0.63455 0.71739 0.42538 11.00000 0.01260 0.01102 0.01272 = 0.00072 0.00132 0.00248 C2 1 0.72515 0.66983 0.54084 11.00000 0.01158 0.01421 0.01200 = 0.00286 0.00182 -0.00106 C3 1 0.70098 0.79435 0.30029 11.00000 0.01471 0.01115 0.01142 = 0.00144 -0.00075 -0.00207 C4 1 0.55974 0.57556 0.37074 11.00000 0.01358 0.01339 0.01291 = 0.00165 0.00024 -0.00073 AFIX 23 H4A 2 0.61416 0.49692 0.32424 11.00000 -1.20000 H4B 2 0.50273 0.61676 0.29937 11.00000 -1.20000 AFIX 0 C5 1 0.48816 0.48644 0.48465 11.00000 0.01806 0.01516 0.01322 = -0.00006 0.00162 -0.00326 AFIX 23 H5A 2 0.43392 0.56441 0.53224 11.00000 -1.20000 H5B 2 0.54469 0.44235 0.55527 11.00000 -1.20000 AFIX 0 C6 1 0.41315 0.34691 0.42302 11.00000 0.01610 0.01352 0.01960 = 0.00011 0.00316 -0.00184 AFIX 23 H6A 2 0.35852 0.30352 0.49593 11.00000 -1.20000 H6B 2 0.36288 0.38905 0.34549 11.00000 -1.20000 AFIX 0 C7 1 0.49317 0.21033 0.36867 11.00000 0.01415 0.01429 0.02540 = -0.00116 0.00107 -0.00213 AFIX 23 H7A 2 0.54855 0.25403 0.29668 11.00000 -1.20000 H7B 2 0.54263 0.16718 0.44648 11.00000 -1.20000 AFIX 0 HKLF 4 END ;