#------------------------------------------------------------------------------ #$Date: 2013-12-28 15:58:47 +0200 (Sat, 28 Dec 2013) $ #$Revision: 91933 $ #$URL: file:///home/coder/svn-repositories/cod/cif/2/20/01/2200180.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_2200180 loop_ _publ_author_name 'Cannon, Debbie' 'Quesada, Antonio' 'Quiroga, Jairo' 'Insuasty, Braulio' 'Abonia, Rodrigo' 'Hern\'andez, Pedro' 'Cobo, Justo' 'Nogueras, Manuel' 'S\'anchez, Adolfo' 'Low, John Nicolson' _publ_section_title ; 5-(1,3-Benzothiazol-2-yliminomethyl)-2,2-dimethyl-1,3-dioxane-4,6-dione ; _journal_issue 2 _journal_name_full 'Acta Crystallographica Section E' _journal_page_first o180 _journal_page_last o181 _journal_volume 57 _journal_year 2001 _chemical_formula_moiety 'C14 H12 N2 O4 S' _chemical_formula_sum 'C14 H12 N2 O4 S' _chemical_formula_weight 304.32 _chemical_melting_point 480 _chemical_name_systematic ; 5-(1,3-Benzothiazol-2-yliminomethyl)-2,2-dimethyl-1,3-dioxane-4,6-dione ; _space_group_IT_number 14 _symmetry_cell_setting monoclinic _symmetry_space_group_name_Hall '-P 2ybc' _symmetry_space_group_name_H-M 'P 1 21/c 1' _cell_angle_alpha 90.00 _cell_angle_beta 103.07(3) _cell_angle_gamma 90.00 _cell_formula_units_Z 4 _cell_length_a 6.3459(13) _cell_length_b 19.235(4) _cell_length_c 11.144(2) _cell_measurement_reflns_used 6132 _cell_measurement_temperature 150.0(10) _cell_measurement_theta_max 30.51 _cell_measurement_theta_min 1.02 _cell_volume 1325.0(5) _computing_cell_refinement 'DENZO-SMN (Otwinowski & Minor, 1997)' _computing_data_collection 'KappaCCD Server Software (Nonius, 1997)' _computing_data_reduction DENZO-SMN _computing_molecular_graphics 'ORTEPII (Johnson, 1976) and PLATON (Spek, 2000)' _computing_publication_material 'SHELXL97 and WordPerfect macro PRPKAPPA (Ferguson, 1999)' _computing_structure_refinement 'SHELXL97 (Sheldrick, 1997)' _computing_structure_solution 'SHELXS97 (Sheldrick, 1997)' _diffrn_ambient_temperature 150.0(10) _diffrn_measured_fraction_theta_full .995 _diffrn_measured_fraction_theta_max .843 _diffrn_measurement_device_type KappaCCD _diffrn_measurement_method '\f and \w scans with \k offsets' _diffrn_radiation_monochromator graphite _diffrn_radiation_source 'fine-focus sealed X-ray tube' _diffrn_radiation_type MoK\a _diffrn_radiation_wavelength .71073 _diffrn_reflns_av_R_equivalents .081 _diffrn_reflns_av_sigmaI/netI .0586 _diffrn_reflns_limit_h_max 8 _diffrn_reflns_limit_h_min -9 _diffrn_reflns_limit_k_max 27 _diffrn_reflns_limit_k_min -22 _diffrn_reflns_limit_l_max 15 _diffrn_reflns_limit_l_min -13 _diffrn_reflns_number 12128 _diffrn_reflns_theta_full 25.00 _diffrn_reflns_theta_max 30.50 _diffrn_reflns_theta_min 2.12 _exptl_absorpt_coefficient_mu .263 _exptl_absorpt_correction_T_max .987 _exptl_absorpt_correction_T_min .908 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details '(DENZO-SMN; Otwinowski & Minor, 1997)' _exptl_crystal_colour orange _exptl_crystal_density_diffrn 1.526 _exptl_crystal_density_method 'not measured' _exptl_crystal_description needle _exptl_crystal_F_000 632 _exptl_crystal_size_max .38 _exptl_crystal_size_mid .05 _exptl_crystal_size_min .05 _refine_diff_density_max .418 _refine_diff_density_min -.516 _refine_ls_extinction_method none _refine_ls_goodness_of_fit_ref 1.076 _refine_ls_hydrogen_treatment constr _refine_ls_matrix_type full _refine_ls_number_parameters 192 _refine_ls_number_reflns 3392 _refine_ls_number_restraints 0 _refine_ls_restrained_S_all 1.076 _refine_ls_R_factor_all .0671 _refine_ls_R_factor_gt .0451 _refine_ls_shift/su_max .001 _refine_ls_shift/su_mean .000 _refine_ls_structure_factor_coef Fsqd _refine_ls_weighting_details 'w = 1/[\s^2^(Fo^2^)+(0.0684P)^2^+0.1432P] where P = (Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_ref .1231 _reflns_number_gt 2645 _reflns_number_total 3392 _reflns_threshold_expression I>2\s(I) _[local]_cod_data_source_file na6043.cif _[local]_cod_data_source_block 1 _[local]_cod_cif_authors_sg_H-M 'P 21/c' _cod_database_code 2200180 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' 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 O1 1.30516(18) .33588(5) 1.01481(10) .0176(3) Uani d . 1 . . O C2 1.2845(3) .26447(8) 1.05018(14) .0160(3) Uani d . 1 . . C C21 1.4987(3) .22996(9) 1.05657(16) .0214(4) Uani d . 1 . . C C22 1.2121(3) .26217(9) 1.17025(14) .0211(4) Uani d . 1 . . C O3 1.13153(17) .22842(6) .95487(10) .0175(3) Uani d . 1 . . O C4 .9419(3) .25966(8) .90183(14) .0164(3) Uani d . 1 . . C O41 .80048(19) .22442(6) .83965(11) .0232(3) Uani d . 1 . . O C5 .9286(2) .33450(8) .92197(14) .0155(3) Uani d . 1 . . C C6 1.1201(2) .37333(8) .97893(13) .0149(3) Uani d . 1 . . C O61 1.12713(19) .43617(6) .99149(10) .0200(3) Uani d . 1 . . O C51 .7346(3) .36591(8) .87199(14) .0164(3) Uani d . 1 . . C N51 .6866(2) .43317(7) .87370(12) .0166(3) Uani d . 1 . . N S51 .41125(6) .54339(2) .82927(4) .01825(14) Uani d . 1 . . S C52 .4810(3) .45697(8) .81356(14) .0159(3) Uani d . 1 . . C N53 .3390(2) .41683(7) .74643(12) .0178(3) Uani d . 1 . . N C54 .1509(3) .45444(8) .70129(15) .0166(3) Uani d . 1 . . C C55 -.0374(3) .42851(9) .62415(15) .0226(4) Uani d . 1 . . C C56 -.2110(3) .47256(10) .58642(17) .0259(4) Uani d . 1 . . C C57 -.2004(3) .54215(9) .62270(17) .0254(4) Uani d . 1 . . C C58 -.0151(3) .56924(9) .69764(15) .0206(4) Uani d . 1 . . C C59 .1594(3) .52439(8) .73635(14) .0164(3) Uani d . 1 . . C H21A 1.4915 .1815 1.0824 .032 Uiso calc R 1 . . H H21B 1.6113 .2545 1.1163 .032 Uiso calc R 1 . . H H21C 1.5332 .2314 .9752 .032 Uiso calc R 1 . . H H22A 1.0651 .2809 1.1577 .032 Uiso calc R 1 . . H H22B 1.3105 .2902 1.2321 .032 Uiso calc R 1 . . H H22C 1.2136 .2140 1.1989 .032 Uiso calc R 1 . . H H51A .6212 .3362 .8314 .020 Uiso calc R 1 . . H H51 .7842 .4628 .9126 .020 Uiso calc R 1 . . H H55 -.0456 .3814 .5982 .027 Uiso calc R 1 . . H H56 -.3404 .4552 .5347 .031 Uiso calc R 1 . . H H57 -.3226 .5714 .5954 .030 Uiso calc R 1 . . H H58 -.0069 .6167 .7219 .025 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 O1 .0176(5) .0113(6) .0220(6) -.0004(4) .0004(5) .0039(4) C2 .0187(8) .0103(7) .0171(8) .0001(6) .0000(6) .0000(6) C21 .0202(8) .0186(8) .0240(9) .0030(7) .0017(7) .0011(7) C22 .0298(9) .0161(8) .0171(8) .0022(7) .0047(7) .0017(6) O3 .0193(6) .0114(6) .0196(6) .0014(4) -.0002(5) -.0022(4) C4 .0180(8) .0146(8) .0163(8) .0018(6) .0035(6) .0004(6) O41 .0215(6) .0173(6) .0278(6) -.0006(5) -.0010(5) -.0078(5) C5 .0183(8) .0126(8) .0147(7) .0005(6) .0015(6) -.0006(6) C6 .0190(8) .0135(8) .0124(7) .0008(6) .0038(6) .0017(6) O61 .0237(6) .0104(6) .0242(6) -.0010(4) .0021(5) -.0006(4) C51 .0184(7) .0147(8) .0154(7) -.0001(6) .0019(6) -.0010(6) N51 .0172(7) .0129(7) .0177(7) .0006(5) -.0001(5) -.0008(5) S51 .0188(2) .0114(2) .0221(2) .00052(14) -.00051(16) -.00246(14) C52 .0202(8) .0120(8) .0151(8) .0004(6) .0030(6) .0005(6) N53 .0198(7) .0138(7) .0181(7) .0014(5) .0004(5) -.0009(5) C54 .0195(8) .0142(8) .0156(8) .0010(6) .0029(6) .0019(6) C55 .0254(9) .0165(8) .0232(9) -.0009(7) -.0004(7) -.0013(7) C56 .0194(8) .0270(9) .0265(9) -.0021(7) -.0046(7) .0022(7) C57 .0195(8) .0264(10) .0276(9) .0060(7) .0000(7) .0060(7) C58 .0236(8) .0147(8) .0233(8) .0037(7) .0047(7) .0009(7) C59 .0181(8) .0154(8) .0150(8) .0001(6) .0026(6) -.0002(6) 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 O1 C6 . 1.3583(18) no O1 C2 . 1.4430(18) no C2 O3 . 1.4439(18) no C2 C21 . 1.500(2) no C2 C22 . 1.511(2) no C21 H21A . .9800 no C21 H21B . .9800 no C21 H21C . .9800 no C22 H22A . .9800 no C22 H22B . .9800 no C22 H22C . .9800 no O3 C4 . 1.3555(18) no C4 O41 . 1.2097(18) no C4 C5 . 1.462(2) no C5 C51 . 1.371(2) no C5 C6 . 1.445(2) no C6 O61 . 1.2164(19) no C51 N51 . 1.330(2) yes C51 H51A . .9500 no N51 C52 . 1.402(2) yes N51 H51 . .8800 no S51 C59 . 1.7355(16) yes S51 C52 . 1.7391(15) yes C52 N53 . 1.290(2) yes N53 C54 . 1.389(2) yes C54 C55 . 1.397(2) no C54 C59 . 1.399(2) no C55 C56 . 1.378(2) no C55 H55 . .9500 no C56 C57 . 1.395(3) no C56 H56 . .9500 no C57 C58 . 1.381(2) no C57 H57 . .9500 no C58 C59 . 1.393(2) no C58 H58 . .9500 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 C6 O1 C2 117.34(12) no O1 C2 O3 110.10(11) no O1 C2 C21 107.27(13) no O3 C2 C21 105.88(12) no O1 C2 C22 109.54(12) no O3 C2 C22 110.41(13) no C21 C2 C22 113.52(14) no C2 C21 H21A 109.5 no C2 C21 H21B 109.5 no H21A C21 H21B 109.5 no C2 C21 H21C 109.5 no H21A C21 H21C 109.5 no H21B C21 H21C 109.5 no C2 C22 H22A 109.5 no C2 C22 H22B 109.5 no H22A C22 H22B 109.5 no C2 C22 H22C 109.5 no H22A C22 H22C 109.5 no H22B C22 H22C 109.5 no C4 O3 C2 119.39(12) no O41 C4 O3 118.15(14) no O41 C4 C5 125.35(14) no O3 C4 C5 116.47(13) no C51 C5 C6 122.64(14) no C51 C5 C4 116.67(14) no C6 C5 C4 120.27(14) no O61 C6 O1 119.10(14) no O61 C6 C5 124.69(14) no O1 C6 C5 116.13(13) no N51 C51 C5 127.59(15) no N51 C51 H51A 116.2 no C5 C51 H51A 116.2 no C51 N51 C52 120.14(14) yes C51 N51 H51 119.9 no C52 N51 H51 119.9 no C59 S51 C52 87.69(8) yes N53 C52 N51 122.31(14) no N53 C52 S51 118.05(12) no N51 C52 S51 119.64(11) no C52 N53 C54 109.19(13) yes N53 C54 C55 125.62(14) no N53 C54 C59 115.11(14) no C55 C54 C59 119.26(15) no C56 C55 C54 118.82(16) no C56 C55 H55 120.6 no C54 C55 H55 120.6 no C55 C56 C57 121.22(16) no C55 C56 H56 119.4 no C57 C56 H56 119.4 no C58 C57 C56 121.05(16) no C58 C57 H57 119.5 no C56 C57 H57 119.5 no C57 C58 C59 117.52(15) no C57 C58 H58 121.2 no C59 C58 H58 121.2 no C58 C59 C54 122.13(15) no C58 C59 S51 127.93(13) no C54 C59 S51 109.94(12) 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 _geom_hbond_publ_flag N51 H51 O61 3_767 .88 2.23 3.028(2) 151 y N51 H51 O61 . .88 2.22 2.807(2) 124 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 _geom_torsion_publ_flag C6 O1 C2 O3 52.11(17) no C6 O1 C2 C21 166.88(13) no C6 O1 C2 C22 -69.48(16) no O1 C2 O3 C4 -44.54(17) no C21 C2 O3 C4 -160.19(13) no C22 C2 O3 C4 76.54(16) no C2 O3 C4 O41 -166.52(13) no C2 O3 C4 C5 15.38(19) no O41 C4 C5 C51 4.2(2) no O3 C4 C5 C51 -177.86(13) no O41 C4 C5 C6 -168.60(15) no O3 C4 C5 C6 9.3(2) no C2 O1 C6 O61 153.43(13) no C2 O1 C6 C5 -29.61(18) no C51 C5 C6 O61 2.3(2) no C4 C5 C6 O61 174.68(15) no C51 C5 C6 O1 -174.44(13) no C4 C5 C6 O1 -2.1(2) no C6 C5 C51 N51 -4.4(3) no C4 C5 C51 N51 -177.04(15) no C5 C51 N51 C52 177.55(15) no C51 N51 C52 N53 -6.1(2) no C51 N51 C52 S51 173.61(12) no C59 S51 C52 N53 .74(14) no C59 S51 C52 N51 -179.02(13) no N51 C52 N53 C54 178.81(14) no S51 C52 N53 C54 -.94(18) no C52 N53 C54 C55 179.34(16) no C52 N53 C54 C59 .7(2) no N53 C54 C55 C56 -179.64(15) no C59 C54 C55 C56 -1.0(3) no C54 C55 C56 C57 .8(3) no C55 C56 C57 C58 .1(3) no C56 C57 C58 C59 -.6(3) no C57 C58 C59 C54 .3(3) no C57 C58 C59 S51 179.63(13) no N53 C54 C59 C58 179.29(14) no C55 C54 C59 C58 .5(3) no N53 C54 C59 S51 -.18(18) no C55 C54 C59 S51 -178.92(13) no C52 S51 C59 C58 -179.69(16) no C52 S51 C59 C54 -.27(12) no _cod_database_fobs_code 2200180 _journal_paper_doi 10.1107/S1600536801001684