#------------------------------------------------------------------------------
#$Date: 2009-11-16 03:43:51 +0200 (Mon, 16 Nov 2009) $
#$Revision: 853 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/2014654.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/
#
# All data on this site have been placed in the public domain by the
# contributors.
#
data_2014654
_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
;
_space_group_IT_number           14
_symmetry_space_group_name_Hall  '-P 2ybc'
_symmetry_space_group_name_H-M   'P 1 21/c 1'
_[local]_cod_cif_authors_sg_H-M  'P 21/c'
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  'C15 H9 Cl1 F3 N O5'
_chemical_formula_sum  'C15 H9 Cl1 F3 N O5'
_chemical_formula_iupac  'C15 H9 Cl1 F3 N O5'
_chemical_formula_weight  375.68
_chemical_melting_point  332.0(10)
_symmetry_cell_setting  monoclinic
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  19.280(5)
_cell_length_b  9.715(3)
_cell_length_c  18.050(5)
_cell_angle_alpha  90.00
_cell_angle_beta  109.509(5)
_cell_angle_gamma  90.00
_cell_volume  3186.8(15)
_cell_formula_units_Z  8
_cell_measurement_temperature  293(2)
_exptl_crystal_density_diffrn  1.566
_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 0.29501(10) 0.76114(13) 0.60249(9) 0.1354(6) Uani d . 1 . . Cl
  F71 0.3742(4) 0.5081(6) 0.9148(2) 0.182(3) Uani d PD 0.827(10) . . F
  F72 0.4480(3) 0.5082(11) 0.8546(3) 0.201(4) Uani d PD 0.827(10) . . F
  F73 0.3870(4) 0.3284(5) 0.8584(3) 0.173(3) Uani d PD 0.827(10) . . F
  O1 0.15154(19) 0.6484(3) 0.5910(2) 0.1265(14) Uani d . 1 . . O
  O2 0.2045(2) 0.2603(3) 0.3961(2) 0.1263(14) Uani d . 1 . . O
  O3 0.12343(16) 0.1541(3) 0.43781(17) 0.0833(9) Uani d . 1 . . O
  O4 0.0453(3) 0.2812(4) 0.2907(2) 0.1469(18) Uani d . 1 . . O
  O5 -0.0419(2) 0.4212(5) 0.2694(2) 0.1589(19) Uani d . 1 . . O
  N1 0.0164(3) 0.3783(6) 0.3102(3) 0.1002(14) Uani d . 1 . . N
  C1 0.2089(3) 0.5935(5) 0.6511(3) 0.0799(14) Uani d . 1 . . C
  C2 0.2784(3) 0.6437(4) 0.6657(3) 0.0704(12) Uani d . 1 . . C
  C3 0.3358(3) 0.6018(4) 0.7306(3) 0.0721(12) Uani d . 1 . . C
  H3 0.3826 0.6386 0.7412 0.086 Uiso calc R 1 . . H
  C4 0.3225(3) 0.5050(5) 0.7790(3) 0.0683(12) Uani d . 1 . . C
  C5 0.2541(4) 0.4511(5) 0.7642(3) 0.0919(15) Uani d . 1 . . C
  H5 0.2459 0.3844 0.7973 0.110 Uiso calc R 1 . . H
  C6 0.1974(3) 0.4958(6) 0.7003(4) 0.0993(17) Uani d . 1 . . C
  H6 0.1506 0.4593 0.6903 0.119 Uiso calc R 1 . . H
  C7 0.3834(4) 0.4605(7) 0.8502(4) 0.1063(18) Uani d D 1 . . C
  C11 0.1191(2) 0.3911(4) 0.4351(2) 0.0630(11) Uani d . 1 . . C
  C12 0.0562(3) 0.4491(5) 0.3831(3) 0.0708(12) Uani d . 1 . . C
  C13 0.0277(2) 0.5701(5) 0.3992(3) 0.0846(14) Uani d . 1 . . C
  H13 -0.0140 0.6080 0.3625 0.102 Uiso calc R 1 . . H
  C14 0.0606(2) 0.6348(5) 0.4689(3) 0.0872(14) Uani d . 1 . . C
  H14 0.0413 0.7164 0.4808 0.105 Uiso calc R 1 . . H
  C15 0.1227(2) 0.5778(5) 0.5216(3) 0.0780(13) Uani d . 1 . . C
  C16 0.1525(2) 0.4573(4) 0.5050(2) 0.0688(12) Uani d . 1 . . C
  H16 0.1951 0.4213 0.5411 0.083 Uiso calc R 1 . . H
  C17 0.1532(3) 0.2617(5) 0.4197(2) 0.0704(12) Uani d . 1 . . C
  C18 0.1502(3) 0.0228(4) 0.4218(3) 0.1033(17) Uani d . 1 . . C
  H18A 0.1378 0.0112 0.3661 0.155 Uiso calc R 1 . . H
  H18B 0.1280 -0.0494 0.4425 0.155 Uiso calc R 1 . . H
  H18C 0.2027 0.0193 0.4463 0.155 Uiso calc R 1 . . H
  F74 0.4198(13) 0.539(2) 0.8858(12) 0.111(7) Uiso d PD 0.173(10) . . F
  F75 0.4347(10) 0.377(2) 0.8287(8) 0.111(7) Uiso d PD 0.173(10) . . F
  F76 0.3558(8) 0.370(3) 0.8897(10) 0.111(7) Uiso d PD 0.173(10) . . F
  Cl1A 0.21997(9) 0.73650(13) 0.38441(8) 0.1254(6) Uani d . 1 . . Cl
  F71A 0.0891(2) 0.5237(5) 0.0679(2) 0.136(2) Uani d PD 0.858(9) . . F
  F72A 0.0348(2) 0.4778(8) 0.1478(3) 0.166(3) Uani d PD 0.858(9) . . F
  F73A 0.0949(2) 0.3220(5) 0.1122(3) 0.154(2) Uani d PD 0.858(9) . . F
  O1A 0.35465(18) 0.6238(3) 0.3665(2) 0.0954(10) Uani d . 1 . . O
  O2A 0.30895(19) 0.2834(3) 0.5934(2) 0.1195(14) Uani d . 1 . . O
  O3A 0.39627(16) 0.1812(3) 0.55869(15) 0.0762(8) Uani d . 1 . . O
  O4A 0.4648(3) 0.3438(5) 0.6969(2) 0.160(2) Uani d . 1 . . O
  O5A 0.5256(2) 0.5276(5) 0.7190(2) 0.1477(17) Uani d . 1 . . O
  N1A 0.4807(2) 0.4506(6) 0.6756(3) 0.0982(14) Uani d . 1 . . N
  C1A 0.2902(3) 0.5716(5) 0.3137(3) 0.0719(12) Uani d . 1 . . C
  C2A 0.2231(3) 0.6224(4) 0.3125(3) 0.0715(12) Uani d . 1 . . C
  C3A 0.1598(3) 0.5844(4) 0.2536(3) 0.0741(12) Uani d . 1 . . C
  H3A 0.1148 0.6218 0.2516 0.089 Uiso calc R 1 . . H
  C4A 0.1630(3) 0.4920(5) 0.1982(3) 0.0706(12) Uani d . 1 . . C
  C5A 0.2289(3) 0.4390(5) 0.2008(3) 0.0868(14) Uani d . 1 . . C
  H5A 0.2309 0.3759 0.1629 0.104 Uiso calc R 1 . . H
  C6A 0.2928(3) 0.4773(5) 0.2588(3) 0.0848(14) Uani d . 1 . . C
  H6A 0.3375 0.4391 0.2605 0.102 Uiso calc R 1 . . H
  C7A 0.0950(4) 0.4560(7) 0.1323(4) 0.1022(18) Uani d D 1 . . C
  C11A 0.3872(2) 0.4171(4) 0.5452(2) 0.0569(10) Uani d . 1 . . C
  C12A 0.4432(2) 0.4951(5) 0.5947(3) 0.0681(12) Uani d . 1 . . C
  C13A 0.4678(2) 0.6134(5) 0.5700(3) 0.0863(14) Uani d . 1 . . C
  H13A 0.5053 0.6649 0.6050 0.104 Uiso calc R 1 . . H
  C14A 0.4368(3) 0.6546(4) 0.4938(3) 0.0859(14) Uani d . 1 . . C
  H14A 0.4535 0.7338 0.4762 0.103 Uiso calc R 1 . . H
  C15A 0.3804(2) 0.5780(4) 0.4428(3) 0.0691(12) Uani d . 1 . . C
  C16A 0.3551(2) 0.4605(4) 0.4682(2) 0.0624(11) Uani d . 1 . . C
  H16A 0.3165 0.4106 0.4338 0.075 Uiso calc R 1 . . H
  C17A 0.3590(3) 0.2881(5) 0.5692(2) 0.0665(11) Uani d . 1 . . C
  C18A 0.3754(3) 0.0499(4) 0.5823(3) 0.0954(15) Uani d . 1 . . C
  H18D 0.3877 0.0480 0.6384 0.143 Uiso calc R 1 . . H
  H18E 0.4014 -0.0223 0.5663 0.143 Uiso calc R 1 . . H
  H18F 0.3234 0.0367 0.5578 0.143 Uiso calc R 1 . . H
  F74A 0.0498(11) 0.584(2) 0.1057(13) 0.122(8) Uiso d PD 0.142(9) . . F
  F75A 0.0499(12) 0.383(3) 0.1554(12) 0.122(8) Uiso d PD 0.142(9) . . F
  F76A 0.1050(9) 0.393(4) 0.0825(12) 0.122(8) Uiso d PD 0.142(9) . . F
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 0.2095(18) 0.0896(9) 0.1154(12) 0.0051(10) 0.0651(11) 0.0311(8)
  F71 0.286(7) 0.193(6) 0.057(3) 0.089(5) 0.044(3) 0.014(3)
  F72 0.093(4) 0.349(11) 0.126(4) -0.008(5) -0.009(3) 0.055(5)
  F73 0.185(5) 0.108(4) 0.184(5) 0.073(3) 0.006(4) 0.018(3)
  O1 0.119(3) 0.088(2) 0.122(3) 0.054(2) -0.027(2) -0.038(2)
  O2 0.125(3) 0.105(3) 0.189(4) -0.034(2) 0.106(3) -0.058(2)
  O3 0.099(2) 0.0573(18) 0.112(2) 0.0063(18) 0.060(2) 0.0059(17)
  O4 0.188(5) 0.117(3) 0.088(3) 0.022(3) -0.017(3) -0.018(2)
  O5 0.094(3) 0.251(5) 0.098(3) 0.031(3) -0.012(2) -0.037(3)
  N1 0.088(4) 0.124(4) 0.078(4) 0.003(4) 0.014(3) 0.012(3)
  C1 0.078(4) 0.065(3) 0.086(4) 0.014(3) 0.014(3) -0.025(3)
  C2 0.099(4) 0.046(3) 0.069(3) 0.008(3) 0.032(3) -0.005(2)
  C3 0.082(4) 0.066(3) 0.074(3) -0.006(3) 0.033(3) -0.014(3)
  C4 0.083(4) 0.071(3) 0.056(3) 0.009(3) 0.031(3) -0.003(3)
  C5 0.109(5) 0.087(4) 0.101(4) -0.003(4) 0.064(4) 0.005(3)
  C6 0.077(4) 0.092(4) 0.139(5) -0.012(3) 0.049(4) -0.014(4)
  C7 0.150(7) 0.088(5) 0.087(5) 0.018(5) 0.047(5) 0.002(4)
  C11 0.064(3) 0.062(3) 0.062(3) -0.007(3) 0.019(2) -0.001(2)
  C12 0.065(3) 0.074(3) 0.065(3) -0.014(3) 0.010(3) -0.001(3)
  C13 0.066(3) 0.086(4) 0.087(4) 0.010(3) 0.006(3) 0.016(3)
  C14 0.066(3) 0.067(3) 0.111(4) 0.021(3) 0.007(3) 0.006(3)
  C15 0.072(3) 0.064(3) 0.087(4) 0.012(3) 0.012(3) -0.008(3)
  C16 0.060(3) 0.059(3) 0.075(3) 0.011(2) 0.005(2) -0.003(2)
  C17 0.065(3) 0.078(3) 0.072(3) -0.009(3) 0.027(3) -0.016(3)
  C18 0.132(5) 0.069(3) 0.119(4) 0.020(3) 0.057(4) -0.013(3)
  Cl1A 0.1726(15) 0.0890(9) 0.1181(11) 0.0154(9) 0.0531(10) -0.0283(8)
  F71A 0.161(4) 0.151(4) 0.072(3) -0.024(3) 0.008(2) 0.024(2)
  F72A 0.086(3) 0.276(8) 0.124(4) -0.003(3) 0.018(3) -0.009(4)
  F73A 0.150(4) 0.115(4) 0.163(4) -0.055(3) 0.006(3) -0.013(3)
  O1A 0.100(3) 0.089(2) 0.089(2) -0.035(2) 0.020(2) 0.0201(19)
  O2A 0.103(3) 0.120(3) 0.171(4) 0.033(2) 0.093(3) 0.062(2)
  O3A 0.093(2) 0.0669(19) 0.078(2) 0.0029(18) 0.0420(17) 0.0004(16)
  O4A 0.236(6) 0.129(3) 0.067(3) -0.017(4) -0.014(3) 0.006(3)
  O5A 0.106(3) 0.219(5) 0.090(3) -0.047(3) -0.004(2) -0.035(3)
  N1A 0.084(3) 0.129(4) 0.069(4) 0.001(3) 0.009(3) -0.028(3)
  C1A 0.080(4) 0.065(3) 0.074(3) -0.016(3) 0.030(3) 0.015(3)
  C2A 0.105(4) 0.053(3) 0.066(3) 0.004(3) 0.041(3) 0.007(2)
  C3A 0.071(3) 0.076(3) 0.079(3) 0.012(3) 0.030(3) 0.017(3)
  C4A 0.073(4) 0.085(3) 0.061(3) -0.010(3) 0.033(3) 0.000(3)
  C5A 0.108(4) 0.091(3) 0.075(4) -0.015(4) 0.050(3) -0.014(3)
  C6A 0.085(4) 0.092(4) 0.092(4) 0.005(3) 0.049(3) 0.002(3)
  C7A 0.104(5) 0.130(6) 0.081(5) -0.015(4) 0.043(4) -0.001(4)
  C11A 0.050(3) 0.066(3) 0.057(3) -0.002(2) 0.021(2) -0.007(2)
  C12A 0.052(3) 0.082(3) 0.066(3) 0.002(3) 0.015(3) -0.017(3)
  C13A 0.063(3) 0.090(4) 0.100(4) -0.017(3) 0.020(3) -0.034(3)
  C14A 0.081(4) 0.063(3) 0.117(4) -0.020(3) 0.037(3) -0.014(3)
  C15A 0.063(3) 0.058(3) 0.085(4) -0.011(2) 0.023(3) -0.003(3)
  C16A 0.066(3) 0.057(3) 0.068(3) -0.014(2) 0.026(2) -0.008(2)
  C17A 0.062(3) 0.081(3) 0.056(3) 0.007(3) 0.020(2) 0.012(2)
  C18A 0.131(4) 0.072(3) 0.085(3) 0.002(3) 0.040(3) 0.019(3)
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 C2 . 1.717(4) ?
  F71 F74 . 1.20(3) ?
  F71 C7 . 1.320(7) ?
  F71 F76 . 1.43(3) ?
  F72 F74 . 0.95(3) ?
  F72 C7 . 1.305(8) ?
  F72 F75 . 1.35(2) ?
  F73 F76 . 1.03(2) ?
  F73 C7 . 1.291(7) ?
  F73 F75 . 1.30(2) ?
  O1 C1 . 1.373(5) ?
  O1 C15 . 1.373(5) ?
  O2 C17 . 1.199(4) ?
  O3 C17 . 1.287(5) ?
  O3 C18 . 1.440(4) ?
  O4 N1 . 1.206(5) ?
  O5 N1 . 1.194(5) ?
  N1 C12 . 1.455(6) ?
  C1 C2 . 1.366(6) ?
  C1 C6 . 1.368(6) ?
  C2 C3 . 1.378(5) ?
  C3 C4 . 1.365(5) ?
  C3 H3 . 0.9300 ?
  C4 C5 . 1.360(6) ?
  C4 C7 . 1.487(7) ?
  C5 C6 . 1.367(6) ?
  C5 H5 . 0.9300 ?
  C6 H6 . 0.9300 ?
  C7 F74 . 1.09(2) ?
  C7 F76 . 1.350(19) ?
  C7 F75 . 1.427(19) ?
  C11 C16 . 1.370(5) ?
  C11 C12 . 1.382(5) ?
  C11 C17 . 1.487(5) ?
  C12 C13 . 1.369(6) ?
  C13 C14 . 1.360(6) ?
  C13 H13 . 0.9300 ?
  C14 C15 . 1.372(5) ?
  C14 H14 . 0.9300 ?
  C15 C16 . 1.380(5) ?
  C16 H16 . 0.9300 ?
  C18 H18A . 0.9600 ?
  C18 H18B . 0.9600 ?
  C18 H18C . 0.9600 ?
  Cl1A C2A . 1.723(4) ?
  F71A C7A . 1.308(6) ?
  F71A F76A . 1.31(3) ?
  F71A F74A . 1.32(3) ?
  F72A F75A . 0.96(3) ?
  F72A C7A . 1.301(6) ?
  F72A F74A . 1.37(2) ?
  F73A F76A . 0.93(3) ?
  F73A C7A . 1.350(7) ?
  F73A F75A . 1.47(3) ?
  O1A C15A . 1.373(5) ?
  O1A C1A . 1.386(5) ?
  O2A C17A . 1.186(4) ?
  O3A C17A . 1.312(5) ?
  O3A C18A . 1.444(4) ?
  O4A N1A . 1.183(5) ?
  O5A N1A . 1.212(5) ?
  N1A C12A . 1.462(6) ?
  C1A C6A . 1.363(6) ?
  C1A C2A . 1.377(6) ?
  C2A C3A . 1.375(6) ?
  C3A C4A . 1.361(5) ?
  C3A H3A . 0.9300 ?
  C4A C5A . 1.357(6) ?
  C4A C7A . 1.488(7) ?
  C5A C6A . 1.373(6) ?
  C5A H5A . 0.9300 ?
  C6A H6A . 0.9300 ?
  C7A F76A . 1.15(2) ?
  C7A F75A . 1.29(3) ?
  C7A F74A . 1.51(2) ?
  C11A C12A . 1.376(5) ?
  C11A C16A . 1.385(5) ?
  C11A C17A . 1.487(5) ?
  C12A C13A . 1.373(6) ?
  C13A C14A . 1.365(6) ?
  C13A H13A . 0.9300 ?
  C14A C15A . 1.384(5) ?
  C14A H14A . 0.9300 ?
  C15A C16A . 1.380(5) ?
  C16A H16A . 0.9300 ?
  C18A H18D . 0.9600 ?
  C18A H18E . 0.9600 ?
  C18A H18F . 0.9600 ?