#------------------------------------------------------------------------------ #$Date: 2013-12-28 13:58:47 +0000 (Sat, 28 Dec 2013) $ #$Revision: 91933 $ #$URL: svn://www.crystallography.net/cod/cif/2/01/13/2011395.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_2011395 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_volume 56 _journal_year 2000 _chemical_formula_moiety 'C12 H12 N2 O4 S' _chemical_formula_sum 'C12 H12 N2 O4 S' _chemical_formula_weight 280.30 _chemical_name_systematic ; 1-cyano-2-hydroxy-N-[4-(methylsulfonyl)phenyl]but-2-enamide ; _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' _cell_angle_alpha 90.00 _cell_angle_beta 97.6440(10) _cell_angle_gamma 90.00 _cell_formula_units_Z 4 _cell_length_a 8.8002(10) _cell_length_b 5.5336(6) _cell_length_c 25.852(3) _cell_measurement_reflns_used 5320 _cell_measurement_temperature 295(2) _cell_measurement_theta_max 26.40 _cell_measurement_theta_min 1.59 _cell_volume 1247.7(2) _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 .985 _diffrn_measured_fraction_theta_max .985 _diffrn_measurement_device_type 'Bruker SMART CCD area-detector' _diffrn_measurement_method \w _diffrn_radiation_type MoK\a _diffrn_radiation_wavelength .71073 _diffrn_reflns_av_R_equivalents .030 _diffrn_reflns_limit_h_max 10 _diffrn_reflns_limit_h_min -11 _diffrn_reflns_limit_k_max 6 _diffrn_reflns_limit_k_min -6 _diffrn_reflns_limit_l_max 31 _diffrn_reflns_limit_l_min -32 _diffrn_reflns_number 10595 _diffrn_reflns_theta_full 26.40 _diffrn_reflns_theta_max 26.40 _diffrn_reflns_theta_min 1.59 _exptl_absorpt_coefficient_mu .271 _exptl_absorpt_correction_T_max .928 _exptl_absorpt_correction_T_min .913 _exptl_absorpt_correction_type empirical _exptl_absorpt_process_details '(SADABS; Sheldrick, 1996)' _exptl_crystal_colour colorless _exptl_crystal_density_diffrn 1.492 _exptl_crystal_density_method 'not measured' _exptl_crystal_description prism _exptl_crystal_F_000 584 _exptl_crystal_size_max .34 _exptl_crystal_size_mid .31 _exptl_crystal_size_min .28 _refine_diff_density_max .23 _refine_diff_density_min -.45 _refine_ls_extinction_method none _refine_ls_goodness_of_fit_ref 1.07 _refine_ls_hydrogen_treatment mixed _refine_ls_matrix_type full _refine_ls_number_parameters 182 _refine_ls_number_reflns 2503 _refine_ls_number_restraints 2 _refine_ls_restrained_S_all 1.066 _refine_ls_R_factor_all .051 _refine_ls_R_factor_gt .044 _refine_ls_shift/su_max .003 _refine_ls_shift/su_mean .000 _refine_ls_structure_factor_coef Fsqd _refine_ls_weighting_details 'calc w = 1/[\s^2^(Fo^2^)+(0.0570P)^2^+0.5101P] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_ref .113 _reflns_number_gt 2157 _reflns_number_total 2503 _reflns_threshold_expression I>2\s(I) _[local]_cod_data_source_file bk1544.cif _[local]_cod_data_source_block PHI492 _[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 2011395 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 S1 .92302(6) .96106(9) .186661(18) .03941(17) Uani d . 1 . . S O1 .7903(2) .8542(3) .20405(7) .0594(4) Uani d . 1 . . O O2 1.04355(19) .8031(3) .17545(6) .0555(4) Uani d . 1 . . O O7 .82385(16) 1.4044(3) -.06543(5) .0446(4) Uani d . 1 . . O O9 .75956(19) 1.5746(3) -.15671(6) .0540(4) Uani d D 1 . . O H9 .799(3) 1.485(5) -.1335(9) .076(9) Uiso d D 1 . . H N1 .71869(19) 1.5741(3) .00206(6) .0389(4) Uani d D 1 . . N H1 .657(2) 1.682(3) .0096(9) .043(6) Uiso d D 1 . . H N11 .5095(2) 2.0899(4) -.05154(8) .0566(5) Uani d . 1 . . N C1 .7722(2) 1.4183(3) .04377(7) .0347(4) Uani d . 1 . . C C2 .8655(2) 1.2177(4) .03973(8) .0404(4) Uani d . 1 . . C H2 .8960 1.1769 .0078 .048 Uiso calc R 1 . . H C3 .9123(2) 1.0798(3) .08344(8) .0388(4) Uani d . 1 . . C H3 .9761 .9475 .0810 .047 Uiso calc R 1 . . H C4 .8650(2) 1.1370(3) .13082(7) .0337(4) Uani d . 1 . . C C5 .7714(2) 1.3354(4) .13495(8) .0413(5) Uani d . 1 . . C H5 .7389 1.3734 .1668 .050 Uiso calc R 1 . . H C6 .7270(2) 1.4751(4) .09191(8) .0422(5) Uani d . 1 . . C H6 .6658 1.6100 .0949 .051 Uiso calc R 1 . . H C7 .7434(2) 1.5618(3) -.04842(8) .0355(4) Uani d . 1 . . C C8 .6686(2) 1.7474(3) -.08386(8) .0366(4) Uani d . 1 . . C C9 .6804(2) 1.7415(4) -.13599(8) .0405(4) Uani d . 1 . . C C10 .6065(3) 1.9207(4) -.17414(9) .0530(6) Uani d . 1 . . C H10A .5829 1.8454 -.2077 .079 Uiso calc R 1 . . H H10B .6752 2.0537 -.1767 .079 Uiso calc R 1 . . H H10C .5138 1.9788 -.1627 .079 Uiso calc R 1 . . H C11 .5806(2) 1.9372(4) -.06545(8) .0407(4) Uani d . 1 . . C C12 .9998(3) 1.1723(4) .23398(8) .0517(5) Uani d . 1 . . C H12A 1.0518 1.0884 .2637 .078 Uiso calc R 1 . . H H12B .9184 1.2682 .2446 .078 Uiso calc R 1 . . H H12C 1.0710 1.2754 .2195 .078 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 S1 .0506(3) .0333(3) .0355(3) .0060(2) .0100(2) .00012(18) O1 .0708(10) .0500(9) .0616(10) -.0100(8) .0247(8) .0067(8) O2 .0685(10) .0520(9) .0462(8) .0283(8) .0079(7) .0012(7) O7 .0515(8) .0398(8) .0448(8) .0173(6) .0143(6) .0045(6) O9 .0674(10) .0517(9) .0441(9) .0244(8) .0125(8) .0043(7) N1 .0438(9) .0332(8) .0403(9) .0129(7) .0079(7) -.0003(7) N11 .0625(12) .0487(11) .0594(12) .0251(10) .0112(10) .0002(9) C1 .0353(9) .0301(9) .0388(10) .0029(7) .0055(7) -.0017(7) C2 .0456(10) .0404(10) .0365(10) .0123(9) .0105(8) -.0025(8) C3 .0431(10) .0346(10) .0397(10) .0115(8) .0088(8) -.0017(8) C4 .0344(9) .0309(9) .0363(9) .0017(7) .0068(7) -.0014(7) C5 .0488(11) .0390(10) .0378(10) .0097(9) .0122(9) -.0038(8) C6 .0472(11) .0352(10) .0451(11) .0141(9) .0095(9) -.0032(8) C7 .0339(9) .0305(9) .0425(10) .0028(7) .0063(8) -.0001(8) C8 .0349(9) .0312(9) .0439(11) .0053(8) .0065(8) .0009(8) C9 .0399(10) .0371(10) .0449(11) .0073(8) .0069(8) .0021(8) C10 .0597(13) .0518(13) .0473(12) .0182(11) .0070(10) .0093(10) C11 .0403(10) .0379(10) .0436(11) .0072(8) .0039(8) .0036(8) C12 .0640(13) .0536(13) .0370(11) .0040(11) .0045(10) -.0069(9) 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 S1 O2 . 1.4336(15) yes S1 O1 . 1.4339(16) yes S1 C4 . 1.7596(19) yes S1 C12 . 1.760(2) yes O7 C7 . 1.239(2) yes O9 C9 . 1.313(2) yes O9 H9 . .819(10) yes N1 C7 . 1.353(3) yes N1 C1 . 1.412(2) yes N1 H1 . .851(10) no N11 C11 . 1.138(2) yes C1 C6 . 1.392(3) no C1 C2 . 1.393(2) no C2 C3 . 1.380(3) no C2 H2 . .9300 no C3 C4 . 1.382(3) no C3 H3 . .9300 no C4 C5 . 1.385(3) no C5 C6 . 1.368(3) no C5 H5 . .9300 no C6 H6 . .9300 no C7 C8 . 1.472(3) yes C8 C9 . 1.366(3) yes C8 C11 . 1.424(3) yes C9 C10 . 1.486(3) yes C10 H10A . .9600 no C10 H10B . .9600 no C10 H10C . .9600 no C12 H12A . .9600 no C12 H12B . .9600 no C12 H12C . .9600 no 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' S S .1246 .1234 '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 O2 S1 O1 117.86(10) yes O2 S1 C4 108.26(9) yes O1 S1 C4 109.02(9) yes O2 S1 C12 108.63(11) yes O1 S1 C12 108.03(11) yes C4 S1 C12 104.20(10) yes C9 O9 H9 109(2) no C7 N1 C1 128.78(16) yes C7 N1 H1 116.6(15) no C1 N1 H1 114.4(15) no C6 C1 C2 119.22(18) no C6 C1 N1 116.07(16) yes C2 C1 N1 124.71(17) yes C3 C2 C1 119.60(17) no C3 C2 H2 120.2 no C1 C2 H2 120.2 no C2 C3 C4 120.46(17) no C2 C3 H3 119.8 no C4 C3 H3 119.8 no C3 C4 C5 120.13(18) no C3 C4 S1 120.80(14) yes C5 C4 S1 119.07(14) yes C6 C5 C4 119.56(17) no C6 C5 H5 120.2 no C4 C5 H5 120.2 no C5 C6 C1 121.01(17) no C5 C6 H6 119.5 no C1 C6 H6 119.5 no O7 C7 N1 123.37(17) yes O7 C7 C8 119.91(17) yes N1 C7 C8 116.72(16) yes C9 C8 C11 117.63(17) yes C9 C8 C7 120.73(17) yes C11 C8 C7 121.64(17) yes O9 C9 C8 122.25(18) yes O9 C9 C10 114.07(18) yes C8 C9 C10 123.69(18) yes C9 C10 H10A 109.5 no C9 C10 H10B 109.5 no H10A C10 H10B 109.5 no C9 C10 H10C 109.5 no H10A C10 H10C 109.5 no H10B C10 H10C 109.5 no N11 C11 C8 178.9(2) yes S1 C12 H12A 109.5 no S1 C12 H12B 109.5 no H12A C12 H12B 109.5 no S1 C12 H12C 109.5 no H12A C12 H12C 109.5 no H12B C12 H12C 109.5 no 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 O9 H9 O7 . .819(10) 1.800(18) 2.534(2) 148(3) N1 H1 N11 3_695 .851(10) 2.307(11) 3.132(2) 164(2) _cod_database_fobs_code 2011395 _journal_paper_doi 10.1107/S0108270100009768