#------------------------------------------------------------------------------ #$Date: 2016-02-19 22:18:51 +0000 (Fri, 19 Feb 2016) $ #$Revision: 176760 $ #$URL: svn://www.crystallography.net/cod/cif/2/01/13/2011394.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_2011394 loop_ _publ_author_name 'Ghosh, Sutapa' 'Jennissen, Jason D.' 'Zheng, Yaguo' 'Uckun, Fatih M.' _publ_section_title ; Three leflunomide metabolite analogs ; _journal_issue 10 _journal_name_full 'Acta Crystallographica Section C' _journal_page_first 1254 _journal_page_last 1257 _journal_paper_doi 10.1107/S0108270100009768 _journal_volume 56 _journal_year 2000 _chemical_formula_moiety 'C12 H8 Br F3 N2 O3' _chemical_formula_sum 'C12 H8 Br F3 N2 O3' _chemical_formula_weight 365.11 _chemical_name_systematic ; 1-cyano-2-hydroxy-N-[3-bromo-4-(trifluromethoxy)phenyl]but-2-enamide ; _space_group_IT_number 2 _symmetry_cell_setting triclinic _symmetry_space_group_name_Hall '-P 1' _symmetry_space_group_name_H-M 'P -1' _audit_creation_method 'manual editing of form.cif' _cell_angle_alpha 69.0090(10) _cell_angle_beta 81.0850(10) _cell_angle_gamma 83.2380(10) _cell_formula_units_Z 2 _cell_length_a 5.2834(4) _cell_length_b 10.8265(8) _cell_length_c 13.1634(10) _cell_measurement_reflns_used 1906 _cell_measurement_temperature 295(2) _cell_measurement_theta_max 25.74 _cell_measurement_theta_min 1.67 _cell_volume 692.91(9) _computing_cell_refinement 'SAINT (Bruker, 1998)' _computing_data_collection 'SMART (Bruker, 1998)' _computing_data_reduction SAINT _computing_molecular_graphics 'SHELXTL (Bruker, 1997)' _computing_publication_material SHELXTL _computing_structure_refinement 'SHELXL97 (Sheldrick, 1997)' _computing_structure_solution 'SHELXS97 (Sheldrick, 1990)' _diffrn_ambient_temperature 295(2) _diffrn_measured_fraction_theta_full .994 _diffrn_measured_fraction_theta_max .994 _diffrn_measurement_device_type 'Bruker SMART CCD area-detector' _diffrn_measurement_method \w _diffrn_radiation_monochromator graphite _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_type MoK\a _diffrn_radiation_wavelength .71073 _diffrn_reflns_av_R_equivalents .037 _diffrn_reflns_av_sigmaI/netI .052 _diffrn_reflns_limit_h_max 6 _diffrn_reflns_limit_h_min -6 _diffrn_reflns_limit_k_max 13 _diffrn_reflns_limit_k_min -13 _diffrn_reflns_limit_l_max 16 _diffrn_reflns_limit_l_min -16 _diffrn_reflns_number 7235 _diffrn_reflns_theta_full 25.74 _diffrn_reflns_theta_max 25.74 _diffrn_reflns_theta_min 1.67 _diffrn_standards_decay_% .05 _exptl_absorpt_coefficient_mu 3.012 _exptl_absorpt_correction_T_max .753 _exptl_absorpt_correction_T_min .344 _exptl_absorpt_correction_type empirical _exptl_absorpt_process_details '(SADABS; Sheldrick, 1996)' _exptl_crystal_colour colorless _exptl_crystal_density_diffrn 1.750 _exptl_crystal_density_meas 1.76(2) _exptl_crystal_density_method 'flotation in phenyliodide and hexane' _exptl_crystal_description needle _exptl_crystal_F_000 360 _exptl_crystal_size_max .45 _exptl_crystal_size_mid .11 _exptl_crystal_size_min .10 _refine_diff_density_max .61 _refine_diff_density_min -.51 _refine_ls_extinction_method none _refine_ls_goodness_of_fit_ref 1.01 _refine_ls_hydrogen_treatment mixed _refine_ls_matrix_type full _refine_ls_number_parameters 200 _refine_ls_number_reflns 2643 _refine_ls_number_restraints 0 _refine_ls_restrained_S_all 1.009 _refine_ls_R_factor_all .103 _refine_ls_R_factor_gt .045 _refine_ls_shift/su_max .004 _refine_ls_shift/su_mean .000 _refine_ls_structure_factor_coef Fsqd _refine_ls_weighting_details 'calc w = 1/[\s^2^(Fo^2^)+(0.0639P)^2^] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_ref .131 _reflns_number_gt 1364 _reflns_number_total 2643 _reflns_threshold_expression I>2\s(I) _cod_data_source_file bk1544.cif _cod_data_source_block PHI495 _cod_depositor_comments ; The following automatic conversions were performed: '_symmetry_cell_setting' value 'Triclinic' changed to 'triclinic' 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 'Triclinic' changed to 'triclinic' 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_original_sg_symbol_H-M P-1 _cod_database_code 2011394 _cod_database_fobs_code 2011394 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' 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 Br1 .18630(13) .49058(6) .37570(5) .1136(4) Uani d . 1 . . Br F1 -.2881(9) .0828(5) .5088(3) .1625(17) Uani d . 1 . . F F2 -.3853(8) .2333(4) .5740(3) .1645(17) Uani d . 1 . . F F3 -.0019(9) .1602(5) .5507(3) .1481(16) Uani d . 1 . . F O4 -.1978(6) .2863(4) .4107(3) .0898(10) Uani d . 1 . . O O7 .5577(5) .1190(3) .0302(2) .0699(9) Uani d . 1 . . O O9 .8665(6) .0708(3) -.1182(3) .0754(10) Uani d . 1 . . O H9 .727(10) .068(5) -.070(5) .109(19) Uiso d . 1 . . H N1 .6152(7) .2897(4) .0847(3) .0552(9) Uani d . 1 . . N H1 .696(7) .355(3) .070(3) .042(11) Uiso d . 1 . . H N11 1.1555(8) .4453(4) -.0794(3) .0810(12) Uani d . 1 . . N C1 .4079(7) .2789(4) .1688(3) .0515(10) Uani d . 1 . . C C2 .2253(8) .1866(4) .1979(3) .0601(11) Uani d . 1 . . C H2 .2345 .1250 .1630 .072 Uiso calc R 1 . . H C3 .0286(8) .1882(5) .2803(3) .0700(12) Uani d . 1 . . C H3 -.0972 .1278 .2997 .084 Uiso calc R 1 . . H C4 .0153(8) .2761(5) .3334(3) .0666(12) Uani d . 1 . . C C5 .1969(9) .3664(4) .3048(3) .0652(12) Uani d . 1 . . C C6 .3926(8) .3670(4) .2232(3) .0611(11) Uani d . 1 . . C H6 .5170 .4280 .2045 .073 Uiso calc R 1 . . H C7 .6795(7) .2146(4) .0208(3) .0518(10) Uani d . 1 . . C C8 .9063(7) .2481(4) -.0615(3) .0507(10) Uani d . 1 . . C C9 .9902(8) .1735(4) -.1260(3) .0582(11) Uani d . 1 . . C C10 1.2180(9) .1980(5) -.2098(4) .0747(13) Uani d . 1 . . C H10A 1.2344 .1339 -.2458 .112 Uiso calc PR .29(5) . . H H10B 1.3690 .1904 -.1752 .112 Uiso calc PR .29(5) . . H H10C 1.1982 .2856 -.2628 .112 Uiso calc PR .29(5) . . H H10D 1.3000 .2727 -.2101 .112 Uiso calc PR .71(5) . . H H10E 1.1654 .2162 -.2807 .112 Uiso calc PR .71(5) . . H H10F 1.3362 .1211 -.1931 .112 Uiso calc PR .71(5) . . H C11 1.0481(8) .3575(4) -.0728(3) .0568(11) Uani d . 1 . . C C12 -.2141(14) .1923(7) .5082(6) .0981(19) Uani d . 1 . . C 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 _atom_site_aniso_type_symbol Br1 .1548(7) .1008(5) .0998(5) -.0162(4) .0380(4) -.0721(4) Br F1 .192(4) .161(4) .140(3) -.090(3) .061(3) -.068(3) F F2 .175(3) .192(4) .109(3) -.017(3) .084(3) -.072(3) F F3 .137(3) .218(5) .070(2) -.035(3) -.002(2) -.025(3) F O4 .076(2) .117(3) .068(2) .0010(19) .0266(18) -.039(2) O O7 .0687(18) .078(2) .079(2) -.0349(17) .0287(15) -.0525(17) O O9 .071(2) .084(2) .091(2) -.0331(18) .0266(19) -.0607(19) O N1 .057(2) .060(2) .057(2) -.0201(19) .0132(17) -.0339(19) N N11 .088(3) .084(3) .081(3) -.038(2) .017(2) -.041(2) N C1 .050(2) .061(3) .047(2) -.011(2) .0060(19) -.025(2) C C2 .058(3) .071(3) .060(3) -.017(2) .010(2) -.036(2) C C3 .067(3) .087(3) .059(3) -.026(2) .019(2) -.033(3) C C4 .059(3) .082(3) .053(3) .000(3) .016(2) -.026(2) C C5 .077(3) .066(3) .057(3) .000(2) .011(2) -.036(2) C C6 .072(3) .061(3) .057(3) -.018(2) .014(2) -.033(2) C C7 .049(2) .061(3) .051(2) -.015(2) .0087(19) -.027(2) C C8 .050(2) .056(2) .049(2) -.0156(19) .0088(19) -.025(2) C C9 .060(3) .064(3) .055(3) -.014(2) .008(2) -.030(2) C C10 .073(3) .088(3) .068(3) -.020(3) .024(2) -.042(3) C C11 .060(3) .064(3) .052(3) -.020(2) .011(2) -.028(2) C C12 .096(5) .129(5) .074(4) -.035(4) .033(4) -.050(4) C loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C .0033 .0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H .0000 .0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N .0061 .0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O .0106 .0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' F F .0171 .0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Br Br -.2901 2.4595 '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 _geom_angle_publ_flag C12 O4 C4 117.6(4) yes C7 N1 C1 128.8(4) yes C6 C1 C2 119.5(3) no C6 C1 N1 116.4(4) yes C2 C1 N1 124.1(4) yes C1 C2 C3 118.4(4) no C4 C3 C2 121.4(4) no C3 C4 C5 119.9(4) no C3 C4 O4 121.6(4) yes C5 C4 O4 118.2(4) yes C4 C5 C6 119.7(4) no C4 C5 Br1 121.4(3) yes C6 C5 Br1 118.8(3) yes C5 C6 C1 121.0(4) no O7 C7 N1 122.7(4) yes O7 C7 C8 119.7(3) yes N1 C7 C8 117.5(4) yes C9 C8 C11 118.7(3) yes C9 C8 C7 121.1(4) yes C11 C8 C7 120.2(3) yes O9 C9 C8 121.0(4) yes O9 C9 C10 114.0(4) yes C8 C9 C10 125.1(4) yes N11 C11 C8 177.9(4) yes F3 C12 F1 105.1(7) yes F3 C12 F2 108.6(6) yes F1 C12 F2 106.6(5) yes F3 C12 O4 114.2(5) yes F1 C12 O4 113.7(6) yes F2 C12 O4 108.2(6) yes loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_site_symmetry_1 _geom_bond_site_symmetry_2 _geom_bond_distance _geom_bond_publ_flag Br1 C5 . . 1.884(4) yes F1 C12 . . 1.288(7) yes F2 C12 . . 1.305(6) yes F3 C12 . . 1.286(7) yes O4 C12 . . 1.319(7) yes O4 C4 . . 1.418(5) yes O7 C7 . . 1.241(5) yes O9 C9 . . 1.320(5) yes N1 C7 . . 1.349(5) yes N1 C1 . . 1.415(5) yes N11 C11 . . 1.134(5) yes C1 C6 . . 1.372(5) no C1 C2 . . 1.383(5) no C2 C3 . . 1.384(6) no C3 C4 . . 1.358(6) no C4 C5 . . 1.365(6) no C5 C6 . . 1.368(5) no C7 C8 . . 1.469(5) yes C8 C9 . . 1.364(5) yes C8 C11 . . 1.427(6) yes C9 C10 . . 1.479(6) yes 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 O9 H9 O7 . .89(6) 1.70(6) 2.508(4) 150(5) yes O9 H9 O7 2_655 .89(6) 2.52(5) 3.027(4) 117(4) yes N1 H1 N11 2_765 .82(3) 2.44(4) 3.218(5) 161(3) yes