data_2014655 _journal_name_full 'Acta Crystallographica, Section C' _journal_year 2005 _journal_volume 61 _journal_page_first o122 _journal_page_last o126 _publ_section_title ; Three trifluoromethyl-substituted protoporphyrinogen-IX oxidase inhibitors ; loop_ _publ_author_name 'Li, Bin' 'Lan, Yu-Ming' 'Hsu, Chi-Tung' 'Liu, Zhen-Long' 'Song, Hai-Bin' 'Wu, Chao' 'Yang, Hua-Zheng' _chemical_formula_moiety 'C14 H10 Cl F3 N2 O4' _chemical_formula_sum 'C14 H10 Cl F3 N2 O4' _chemical_formula_iupac 'C14 H10 Cl F3 N2 O4' _chemical_formula_weight 362.69 _chemical_melting_point 443.0(10) _symmetry_cell_setting Monoclinic _symmetry_space_group_name_H-M 'P 21/n' 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 14.326(13) _cell_length_b 7.802(7) _cell_length_c 14.337(13) _cell_angle_alpha 90.00 _cell_angle_beta 110.599(15) _cell_angle_gamma 90.00 _cell_volume 1500(2) _cell_formula_units_Z 4 _cell_measurement_temperature 293(2) _exptl_crystal_density_diffrn 1.606 _diffrn_ambient_temperature 293(2) loop_ _atom_site_label _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_calc_flag _atom_site_refinement_flags _atom_site_occupancy _atom_site_disorder_assembly _atom_site_disorder_group _atom_site_type_symbol Cl1 0.07694(7) 0.88697(10) 0.19239(6) 0.0751(3) Uani d . 1 . . Cl F71 0.21795(16) -0.1887(2) 0.68455(15) 0.0899(7) Uani d . 1 . . F F72 0.32208(15) -0.0282(2) 0.78845(11) 0.0697(5) Uani d . 1 . . F F73 0.36128(17) -0.1549(3) 0.67724(14) 0.0861(7) Uani d . 1 . . F O1 0.33607(14) 0.4512(3) 0.55205(15) 0.0635(6) Uani d . 1 . . O O2 0.02759(13) 0.2154(3) 0.43625(14) 0.0581(5) Uani d . 1 . . O O3 0.1805(2) 0.6179(3) 0.11095(17) 0.0864(8) Uani d . 1 . . O O4 0.12446(17) 0.3650(3) 0.13431(14) 0.0606(6) Uani d . 1 . . O N1 0.18198(14) 0.3337(2) 0.49334(13) 0.0349(5) Uani d . 1 . . N N3 0.31324(14) 0.2012(3) 0.62138(14) 0.0391(5) Uani d . 1 . . N C2 0.28141(18) 0.3369(3) 0.55551(17) 0.0394(6) Uani d . 1 . . C C4 0.24823(18) 0.0740(3) 0.62383(17) 0.0370(6) Uani d . 1 . . C C5 0.15265(19) 0.0750(3) 0.56586(18) 0.0419(6) Uani d . 1 . . C H5 0.1108 -0.0120 0.5720 0.050 Uiso calc R 1 . . H C6 0.11304(18) 0.2085(3) 0.49387(18) 0.0394(6) Uani d . 1 . . C C7 0.2883(2) -0.0737(4) 0.6940(2) 0.0499(7) Uani d . 1 . . C C8 0.4187(2) 0.2073(5) 0.6862(2) 0.0699(10) Uani d . 1 . . C H8A 0.4290 0.1339 0.7427 0.105 Uiso calc R 1 . . H H8B 0.4364 0.3227 0.7086 0.105 Uiso calc R 1 . . H H8C 0.4595 0.1691 0.6496 0.105 Uiso calc R 1 . . H C11 0.14032(17) 0.5648(3) 0.25663(17) 0.0372(6) Uani d . 1 . . C C12 0.10602(19) 0.7209(3) 0.27755(19) 0.0435(6) Uani d . 1 . . C C13 0.0911(2) 0.7464(4) 0.3663(2) 0.0512(7) Uani d . 1 . . C H13 0.0653 0.8502 0.3782 0.061 Uiso calc R 1 . . H C14 0.1139(2) 0.6196(3) 0.43735(19) 0.0466(6) Uani d . 1 . . C H14 0.1036 0.6367 0.4972 0.056 Uiso calc R 1 . . H C15 0.15216(17) 0.4672(3) 0.41879(17) 0.0357(5) Uani d . 1 . . C C16 0.16351(17) 0.4382(3) 0.32921(17) 0.0357(5) Uani d . 1 . . C H16 0.1870 0.3326 0.3169 0.043 Uiso calc R 1 . . H C17 0.15162(19) 0.5245(4) 0.15984(18) 0.0439(6) Uani d . 1 . . C C18 0.1284(3) 0.3052(5) 0.0407(2) 0.0793(11) Uani d . 1 . . C H18A 0.1937 0.3255 0.0386 0.119 Uiso calc R 1 . . H H18B 0.0798 0.3655 -0.0130 0.119 Uiso calc R 1 . . H H18C 0.1142 0.1846 0.0340 0.119 Uiso calc R 1 . . H loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_12 _atom_site_aniso_U_13 _atom_site_aniso_U_23 Cl1 0.0942(7) 0.0516(5) 0.0700(5) 0.0180(4) 0.0171(5) 0.0255(4) F71 0.1013(16) 0.0612(12) 0.0870(14) -0.0221(11) 0.0081(12) 0.0321(10) F72 0.1064(14) 0.0615(11) 0.0346(9) 0.0083(10) 0.0165(9) 0.0090(8) F73 0.1133(16) 0.0802(13) 0.0721(12) 0.0521(12) 0.0416(12) 0.0223(11) O1 0.0468(11) 0.0647(13) 0.0636(13) -0.0223(10) 0.0001(9) 0.0202(11) O2 0.0398(11) 0.0680(13) 0.0560(12) -0.0102(9) 0.0036(9) 0.0113(10) O3 0.135(2) 0.0793(17) 0.0610(14) -0.0390(16) 0.0538(15) -0.0009(12) O4 0.0907(16) 0.0538(12) 0.0506(12) -0.0072(11) 0.0415(11) -0.0092(9) N1 0.0352(10) 0.0373(11) 0.0301(10) -0.0024(9) 0.0090(8) 0.0011(9) N3 0.0338(11) 0.0482(12) 0.0319(10) -0.0021(9) 0.0072(8) 0.0063(9) C2 0.0377(13) 0.0437(14) 0.0334(13) -0.0072(12) 0.0081(11) 0.0026(11) C4 0.0464(14) 0.0378(13) 0.0296(12) -0.0010(11) 0.0167(11) -0.0012(10) C5 0.0470(15) 0.0398(14) 0.0393(13) -0.0096(11) 0.0156(12) 0.0015(11) C6 0.0383(14) 0.0445(14) 0.0351(13) -0.0061(11) 0.0124(11) -0.0029(11) C7 0.0642(18) 0.0450(15) 0.0412(15) 0.0033(14) 0.0192(13) 0.0047(12) C8 0.0397(16) 0.090(2) 0.066(2) -0.0078(16) 0.0002(14) 0.0288(18) C11 0.0359(13) 0.0386(13) 0.0337(12) -0.0026(10) 0.0083(10) 0.0027(10) C12 0.0435(14) 0.0369(14) 0.0417(14) 0.0028(11) 0.0044(11) 0.0061(11) C13 0.0572(17) 0.0403(15) 0.0501(16) 0.0136(13) 0.0114(13) -0.0036(12) C14 0.0522(15) 0.0480(16) 0.0389(14) 0.0069(13) 0.0152(12) -0.0063(12) C15 0.0364(13) 0.0362(13) 0.0316(12) -0.0016(10) 0.0083(10) 0.0008(10) C16 0.0365(12) 0.0332(12) 0.0357(13) 0.0024(10) 0.0106(10) 0.0003(10) C17 0.0433(14) 0.0496(16) 0.0371(13) -0.0015(12) 0.0121(12) 0.0059(12) C18 0.103(3) 0.090(3) 0.0538(19) 0.004(2) 0.0383(19) -0.0206(18) loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_site_symmetry_2 _geom_bond_distance _geom_bond_publ_flag Cl1 C12 . 1.728(3) ? F71 C7 . 1.321(3) ? F72 C7 . 1.316(3) ? F73 C7 . 1.315(3) ? O1 C2 . 1.199(3) ? O2 C6 . 1.213(3) ? O3 C17 . 1.182(3) ? O4 C17 . 1.317(3) ? O4 C18 . 1.441(4) ? N1 C2 . 1.390(3) ? N1 C6 . 1.391(3) ? N1 C15 . 1.445(3) ? N3 C4 . 1.370(3) ? N3 C2 . 1.385(3) ? N3 C8 . 1.470(3) ? C4 C5 . 1.329(4) ? C4 C7 . 1.504(4) ? C5 C6 . 1.435(4) ? C5 H5 . 0.9300 ? C8 H8A . 0.9600 ? C8 H8B . 0.9600 ? C8 H8C . 0.9600 ? C11 C12 . 1.385(4) ? C11 C16 . 1.387(3) ? C11 C17 . 1.486(4) ? C12 C13 . 1.377(4) ? C13 C14 . 1.375(4) ? C13 H13 . 0.9300 ? C14 C15 . 1.374(4) ? C14 H14 . 0.9300 ? C15 C16 . 1.369(3) ? C16 H16 . 0.9300 ? C18 H18A . 0.9600 ? C18 H18B . 0.9600 ? C18 H18C . 0.9600 ?