#------------------------------------------------------------------------------ #$Date: 2013-12-28 15:58:47 +0200 (Sat, 28 Dec 2013) $ #$Revision: 91933 $ #$URL: file:///home/coder/svn-repositories/cod/cif/2/01/46/2014655.cif $ #------------------------------------------------------------------------------ # # This file is available in the Crystallography Open Database (COD), # http://www.crystallography.net/. The original data for this entry # were provided by IUCr Journals, http://journals.iucr.org/. # # The file may be used within the scientific community so long as # proper attribution is given to the journal article from which the # data were obtained. # data_2014655 loop_ _publ_author_name 'Li, Bin' 'Lan, Yu-Ming' 'Hsu, Chi-Tung' 'Liu, Zhen-Long' 'Song, Hai-Bin' 'Wu, Chao' 'Yang, Hua-Zheng' _publ_section_title ; Three trifluoromethyl-substituted protoporphyrinogen IX oxidase inhibitors ; _journal_issue 2 _journal_name_full 'Acta Crystallographica Section C' _journal_page_first o122 _journal_page_last o126 _journal_volume 61 _journal_year 2005 _chemical_formula_iupac 'C14 H10 Cl F3 N2 O4' _chemical_formula_moiety 'C14 H10 Cl F3 N2 O4' _chemical_formula_sum 'C14 H10 Cl F3 N2 O4' _chemical_formula_weight 362.69 _chemical_melting_point 443.0(10) _chemical_name_systematic ;methyl 2-chloro-5-[3-methyl-2,6-dioxo-4-(trifluoromethyl)-1,2,3,6-tetrahydropyrimidin- 1-yl]benzoate ; _space_group_IT_number 14 _symmetry_cell_setting monoclinic _symmetry_space_group_name_Hall '-P 2yn' _symmetry_space_group_name_H-M 'P 1 21/n 1' _atom_sites_solution_hydrogens geom _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _cell_angle_alpha 90.00 _cell_angle_beta 110.599(15) _cell_angle_gamma 90.00 _cell_formula_units_Z 4 _cell_length_a 14.326(13) _cell_length_b 7.802(7) _cell_length_c 14.337(13) _cell_measurement_reflns_used 823 _cell_measurement_temperature 293(2) _cell_measurement_theta_max 25.36 _cell_measurement_theta_min 2.50 _cell_volume 1500(2) _computing_cell_refinement SMART _computing_data_collection 'SMART (Bruker, 1998)' _computing_data_reduction 'SAINT (Bruker, 1999)' _computing_molecular_graphics 'PLATON (Spek, 2003)' _computing_publication_material SHELXL97 _computing_structure_refinement 'SHELXL97 (Sheldrick, 1997) in WinGX (Farrugia, 1999)' _computing_structure_solution 'SHELXS97 (Sheldrick, 1997)' _diffrn_ambient_temperature 293(2) _diffrn_measured_fraction_theta_full 1.000 _diffrn_measured_fraction_theta_max 1.000 _diffrn_measurement_device_type 'Bruker SMART CCD area-detector' _diffrn_measurement_method '\f and \w' _diffrn_radiation_monochromator graphite _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_type MoK\a _diffrn_radiation_wavelength 0.71073 _diffrn_reflns_av_R_equivalents 0.0215 _diffrn_reflns_av_sigmaI/netI 0.0233 _diffrn_reflns_limit_h_max 17 _diffrn_reflns_limit_h_min -12 _diffrn_reflns_limit_k_max 9 _diffrn_reflns_limit_k_min -9 _diffrn_reflns_limit_l_max 15 _diffrn_reflns_limit_l_min -17 _diffrn_reflns_number 7542 _diffrn_reflns_theta_full 25.00 _diffrn_reflns_theta_max 25.00 _diffrn_reflns_theta_min 2.50 _diffrn_standards_interval_count 0 _diffrn_standards_interval_time 0 _diffrn_standards_number 0 _exptl_absorpt_coefficient_mu 0.312 _exptl_absorpt_correction_T_max 1.000000 _exptl_absorpt_correction_T_min 0.806256 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details '(SADABS; Sheldrick, 1996)' _exptl_crystal_colour colourless _exptl_crystal_density_diffrn 1.606 _exptl_crystal_density_meas 'not measured' _exptl_crystal_density_method 'not measured' _exptl_crystal_description prism _exptl_crystal_F_000 736 _exptl_crystal_size_max 0.26 _exptl_crystal_size_mid 0.22 _exptl_crystal_size_min 0.16 _refine_diff_density_max 0.262 _refine_diff_density_min -0.339 _refine_ls_extinction_coef 0.0072(12) _refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^ _refine_ls_extinction_method 'SHELXL97 (Sheldrick, 1997)' _refine_ls_goodness_of_fit_ref 1.103 _refine_ls_hydrogen_treatment constr _refine_ls_matrix_type full _refine_ls_number_parameters 220 _refine_ls_number_reflns 2646 _refine_ls_number_restraints 0 _refine_ls_restrained_S_all 1.103 _refine_ls_R_factor_all 0.0560 _refine_ls_R_factor_gt 0.0389 _refine_ls_shift/su_max 0.006 _refine_ls_shift/su_mean 0.000 _refine_ls_structure_factor_coef Fsqd _refine_ls_weighting_details 'calc w = 1/[\s^2^(Fo^2^)+(0.0399P)^2^+1.2049P] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_gt 0.1035 _refine_ls_wR_factor_ref 0.1151 _reflns_number_gt 2007 _reflns_number_total 2646 _reflns_threshold_expression I>2\s(I) _[local]_cod_data_source_file fg1802.cif _[local]_cod_data_source_block II _[local]_cod_cif_authors_sg_H-M 'P 21/n' _cod_depositor_comments ; The following automatic conversions were performed: '_symmetry_cell_setting' value 'Monoclinic' changed to 'monoclinic' according to '/home/saulius/struct/CIF-dictionaries/cif_core.dic' dictionary named 'cif_core.dic' version 2.4.1 from 2010-06-29. Automatic conversion script Id: cif_fix_enum 1527 2010-12-29 10:47:43Z saulius The following automatic conversions were performed: '_symmetry_cell_setting' value 'Monoclinic' changed to 'monoclinic' according to /home/saulius/struct/CIF-dictionaries/cif_core.dic dictionary named 'cif_core.dic' version 2.4.1 from 2010-06-29. Automatic conversion script Id: cif_fix_values 1715 2011-07-08 13:25:40Z adriana ; _cod_database_code 2014655 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' 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 ? 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' 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' F F 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle C17 O4 C18 117.4(2) C2 N1 C6 125.4(2) C2 N1 C15 115.53(19) C6 N1 C15 118.98(19) C4 N3 C2 120.5(2) C4 N3 C8 124.3(2) C2 N3 C8 115.1(2) O1 C2 N3 122.2(2) O1 C2 N1 121.6(2) N3 C2 N1 116.2(2) C5 C4 N3 122.7(2) C5 C4 C7 119.3(2) N3 C4 C7 118.0(2) C4 C5 C6 120.9(2) C4 C5 H5 119.5 C6 C5 H5 119.5 O2 C6 N1 120.9(2) O2 C6 C5 124.8(2) N1 C6 C5 114.3(2) F73 C7 F72 106.9(2) F73 C7 F71 106.3(3) F72 C7 F71 106.2(2) F73 C7 C4 112.8(2) F72 C7 C4 113.4(2) F71 C7 C4 110.7(2) N3 C8 H8A 109.5 N3 C8 H8B 109.5 H8A C8 H8B 109.5 N3 C8 H8C 109.5 H8A C8 H8C 109.5 H8B C8 H8C 109.5 C12 C11 C16 118.2(2) C12 C11 C17 123.5(2) C16 C11 C17 118.3(2) C13 C12 C11 120.6(2) C13 C12 Cl1 117.9(2) C11 C12 Cl1 121.5(2) C14 C13 C12 120.5(2) C14 C13 H13 119.8 C12 C13 H13 119.8 C15 C14 C13 119.1(2) C15 C14 H14 120.5 C13 C14 H14 120.5 C16 C15 C14 120.8(2) C16 C15 N1 118.2(2) C14 C15 N1 121.0(2) C15 C16 C11 120.6(2) C15 C16 H16 119.7 C11 C16 H16 119.7 O3 C17 O4 123.3(3) O3 C17 C11 126.8(3) O4 C17 C11 109.9(2) O4 C18 H18A 109.5 O4 C18 H18B 109.5 H18A C18 H18B 109.5 O4 C18 H18C 109.5 H18A C18 H18C 109.5 H18B C18 H18C 109.5 loop_ _geom_hbond_atom_site_label_D _geom_hbond_atom_site_label_H _geom_hbond_atom_site_label_A _geom_hbond_site_symmetry_A _geom_hbond_distance_DH _geom_hbond_distance_HA _geom_hbond_distance_DA _geom_hbond_angle_DHA _geom_hbond_publ_flag C5 H5 O2 3_556 0.93 2.51 3.427(4) 169 y C16 H16 O3 2_545 0.93 2.47 3.260(4) 143 y 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 C4 N3 C2 O1 179.3(2) C8 N3 C2 O1 -0.2(4) C4 N3 C2 N1 -0.6(3) C8 N3 C2 N1 179.9(2) C6 N1 C2 O1 -178.5(2) C15 N1 C2 O1 5.7(3) C6 N1 C2 N3 1.4(3) C15 N1 C2 N3 -174.4(2) C2 N3 C4 C5 -1.3(4) C8 N3 C4 C5 178.2(3) C2 N3 C4 C7 177.5(2) C8 N3 C4 C7 -3.1(4) N3 C4 C5 C6 2.4(4) C7 C4 C5 C6 -176.3(2) C2 N1 C6 O2 -179.5(2) C15 N1 C6 O2 -3.8(3) C2 N1 C6 C5 -0.3(3) C15 N1 C6 C5 175.4(2) C4 C5 C6 O2 177.6(3) C4 C5 C6 N1 -1.6(3) C5 C4 C7 F73 120.6(3) N3 C4 C7 F73 -58.2(3) C5 C4 C7 F72 -117.7(3) N3 C4 C7 F72 63.5(3) C5 C4 C7 F71 1.6(3) N3 C4 C7 F71 -177.2(2) C16 C11 C12 C13 -3.0(4) C17 C11 C12 C13 175.7(2) C16 C11 C12 Cl1 179.11(19) C17 C11 C12 Cl1 -2.2(3) C11 C12 C13 C14 2.7(4) Cl1 C12 C13 C14 -179.3(2) C12 C13 C14 C15 0.2(4) C13 C14 C15 C16 -2.9(4) C13 C14 C15 N1 176.8(2) C2 N1 C15 C16 87.7(3) C6 N1 C15 C16 -88.4(3) C2 N1 C15 C14 -92.0(3) C6 N1 C15 C14 91.9(3) C14 C15 C16 C11 2.6(4) N1 C15 C16 C11 -177.1(2) C12 C11 C16 C15 0.3(4) C17 C11 C16 C15 -178.4(2) C18 O4 C17 O3 -1.5(4) C18 O4 C17 C11 178.5(2) C12 C11 C17 O3 38.9(4) C16 C11 C17 O3 -142.4(3) C12 C11 C17 O4 -141.1(3) C16 C11 C17 O4 37.6(3) _journal_paper_doi 10.1107/S0108270105000545