#------------------------------------------------------------------------------ #$Date: 2011-09-10 04:16:28 +0100 (Sat, 10 Sep 2011) $ #$Revision: 25271 $ #$URL: svn://www.crystallography.net/cod/cif/2/2011281.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_2011281 loop_ _publ_author_name 'Maiti, Susim' 'Mukherjee, Monika' 'Nandi, Bidisha' 'Helliwell, Madeleine' 'Kundu, Nitya G.' _publ_section_title ; (E)-2-[2-(1-Naphthyl)vinyl]-3-tosyl-2,3-dihydro-1,3-benzothiazole ; _journal_issue 8 _journal_name_full 'Acta Crystallographica Section C' _journal_page_first 992 _journal_page_last 994 _journal_volume 56 _journal_year 2000 _chemical_formula_analytical 'C26 H21 N O2 S2' _chemical_formula_moiety 'C26 H21 N O2 S2' _chemical_formula_structural 'C26 H21 N O2 S2' _chemical_formula_sum 'C26 H21 N O2 S2' _chemical_formula_weight 443.56 _chemical_name_systematic ; (E)-2-(2-\a-Naphthyl)vinyl-3-p-tosyl benzothiazoline ; _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' _audit_creation_method SHELXL-97 _cell_angle_alpha 90.00 _cell_angle_beta 98.52(4) _cell_angle_gamma 90.00 _cell_formula_units_Z 4 _cell_length_a 10.006(4) _cell_length_b 8.543(3) _cell_length_c 26.090(10) _cell_measurement_reflns_used 20 _cell_measurement_temperature 296.2 _cell_measurement_theta_max 16.4 _cell_measurement_theta_min 14.4 _cell_volume 2205.6(15) _computing_cell_refinement 'MSC/AFC Diffractometer Control Software' _computing_data_collection ; MSC/AFC Diffractometer Control Software (Molecular Structure Corporation, 1994) ; _computing_data_reduction 'TEXSAN (Molecular Structure Corporation, 1995)' _computing_molecular_graphics 'ZORTEP (Zsolnai, 1995)' _computing_publication_material SHELXL97 _computing_structure_refinement 'SHELXL97 (Sheldrick, 1997)' _computing_structure_solution 'MULTAN88 (Debaerdemaeker et al., 1988)' _diffrn_ambient_temperature 296.2 _diffrn_measured_fraction_theta_full .946 _diffrn_measured_fraction_theta_max .946 _diffrn_measurement_device_type 'Rigaku AFC-5R' _diffrn_measurement_method \w-2\q _diffrn_radiation_monochromator graphite _diffrn_radiation_source 'Rigaku rotating anode' _diffrn_radiation_type CuK\a _diffrn_radiation_wavelength 1.54180 _diffrn_reflns_av_R_equivalents .0388 _diffrn_reflns_av_sigmaI/netI .0827 _diffrn_reflns_limit_h_max 11 _diffrn_reflns_limit_h_min -12 _diffrn_reflns_limit_k_max 10 _diffrn_reflns_limit_k_min -8 _diffrn_reflns_limit_l_max 32 _diffrn_reflns_limit_l_min -33 _diffrn_reflns_number 4742 _diffrn_reflns_theta_full 78.26 _diffrn_reflns_theta_max 78.26 _diffrn_reflns_theta_min 3.43 _diffrn_standards_decay_% 4.20 _diffrn_standards_interval_count 150 _diffrn_standards_number 3 _exptl_absorpt_coefficient_mu 2.371 _exptl_absorpt_correction_T_max .6485 _exptl_absorpt_correction_T_min .5365 _exptl_absorpt_correction_type empirical _exptl_absorpt_process_details '(North et al., 1968)' _exptl_crystal_colour colourless _exptl_crystal_density_diffrn 1.336 _exptl_crystal_density_meas 'not measured' _exptl_crystal_density_method none _exptl_crystal_description prismatic _exptl_crystal_F_000 928 _exptl_crystal_size_max .30 _exptl_crystal_size_mid .30 _exptl_crystal_size_min .20 _refine_diff_density_max .437 _refine_diff_density_min -.697 _refine_ls_extinction_coef none _refine_ls_extinction_method none _refine_ls_goodness_of_fit_ref 1.012 _refine_ls_hydrogen_treatment constr _refine_ls_matrix_type full _refine_ls_number_parameters 282 _refine_ls_number_reflns 4476 _refine_ls_number_restraints 0 _refine_ls_restrained_S_all 1.012 _refine_ls_R_factor_all .144 _refine_ls_R_factor_gt .069 _refine_ls_shift/su_max .021 _refine_ls_shift/su_mean .000 _refine_ls_structure_factor_coef Fsqd _refine_ls_weighting_details 'calc w = 1/[\s^2^(Fo^2^)+(0.1300P)^2^] where P = (Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_ref .225 _reflns_number_gt 2609 _reflns_number_total 4476 _reflns_threshold_expression I>2\s(I) _[local]_cod_data_source_file sk1385.cif _[local]_cod_data_source_block II _[local]_cod_cif_authors_sg_H-M 'P 21/n' _cod_original_cell_volume 2205.0(10) _cod_database_code 2011281 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_type_symbol S1 .68306(12) .12191(12) .13897(4) .0418(3) Uani d . 1 S S2 .72636(13) -.31393(14) .19327(4) .0487(3) Uani d . 1 S N .6235(4) -.0549(4) .14712(12) .0394(8) Uani d . 1 N O1 .5988(4) .1867(4) .09521(12) .0561(9) Uani d . 1 O O2 .6927(4) .1978(4) .18794(12) .0545(9) Uani d . 1 O C1 .9521(6) .0613(7) .1587(2) .0624(14) Uani d . 1 C H1 .9382 .0418 .1926 .075 Uiso calc R 1 H C2 1.0811(6) .0500(7) .1455(3) .0713(16) Uani d . 1 C H2 1.1525 .0200 .1706 .086 Uiso calc R 1 H C3 1.1052(7) .0822(7) .0964(3) .0737(17) Uani d . 1 C C4 1.2456(7) .0734(10) .0824(3) .118(4) Uani d . 1 C H4A 1.291(3) .161(6) .093(2) .176 Uiso calc R 1 H H4B 1.2406(8) .064(8) .0478(19) .176 Uiso calc R 1 H H4C 1.289(3) -.010(6) .098(2) .176 Uiso calc R 1 H C5 .9983(8) .1224(9) .0605(3) .093(2) Uani d . 1 C H5 1.0134 .1440 .0269 .112 Uiso calc R 1 H C6 .8674(6) .1325(8) .0720(2) .0724(17) Uani d . 1 C H6 .7962 .1597 .0464 .087 Uiso calc R 1 H C7 .8447(5) .1014(5) .12186(16) .0425(10) Uani d . 1 C C8 .6233(4) -.1704(5) .10762(14) .0367(9) Uani d . 1 C C9 .5751(5) -.1500(6) .05554(16) .0518(12) Uani d . 1 C H9 .5357 -.0558 .0435 .062 Uiso calc R 1 H C10 .5865(6) -.2721(6) .02197(17) .0591(14) Uani d . 1 C H10 .5562 -.2595 -.0132 .071 Uiso calc R 1 H C11 .6420(5) -.4117(6) .0399(2) .0568(13) Uani d . 1 C H11 .6507 -.4920 .0165 .068 Uiso calc R 1 H C12 .6859(5) -.4355(6) .09261(19) .0500(12) Uani d . 1 C H12 .7204 -.5318 .1048 .060 Uiso calc R 1 H C13 .6767(4) -.3126(5) .12603(15) .0369(9) Uani d . 1 C C14 .6411(4) -.1258(5) .19956(16) .0395(10) Uani d . 1 C H14 .6991 -.0583 .2238 .047 Uiso calc . 1 H C15 .5076(5) -.1458(6) .21776(16) .0453(11) Uani d . 1 C H15 .4398 -.1988 .1964 .054 Uiso calc R 1 H C16 .4810(5) -.0932(6) .26178(17) .0460(11) Uani d . 1 C H16 .5524 -.0446 .2827 .055 Uiso calc R 1 H C17 .3535(5) -.1002(5) .28294(17) .0429(10) Uani d . 1 C C18 .2433(5) -.1782(7) .2576(2) .0590(13) Uani d . 1 C H18 .2516 -.2322 .2273 .071 Uiso calc R 1 H C19 .1185(5) -.1788(7) .2760(2) .0661(15) Uani d . 1 C H19 .0449 -.2302 .2574 .079 Uiso calc R 1 H C20 .1049(6) -.1052(7) .3207(2) .0632(14) Uani d . 1 C H20 .0220 -.1073 .3327 .076 Uiso calc R 1 H C21 .2130(5) -.0261(6) .3491(2) .0515(12) Uani d . 1 C C22 .2014(7) .0518(7) .3966(2) .0725(17) Uani d . 1 C H22 .1190 .0510 .4090 .087 Uiso calc R 1 H C23 .3057(7) .1254(9) .4234(2) .088(2) Uani d . 1 C H23 .2951 .1747 .4543 .106 Uiso calc R 1 H C24 .4305(7) .1304(9) .4062(2) .090(2) Uani d . 1 C H24 .5029 .1813 .4258 .108 Uiso calc R 1 H C25 .4465(6) .0597(7) .3602(2) .0630(15) Uani d . 1 C H25 .5296 .0666 .3485 .076 Uiso calc R 1 H C26 .3403(5) -.0231(5) .33032(17) .0422(10) 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 S1 .0519(7) .0315(5) .0425(6) .0052(5) .0091(5) .0003(4) S2 .0608(8) .0507(7) .0350(5) .0172(6) .0087(5) .0079(5) N .054(2) .0349(18) .0311(17) .0020(16) .0113(16) .0013(14) O1 .066(2) .0441(18) .0560(19) .0105(17) .0009(17) .0132(16) O2 .074(2) .0434(18) .0487(18) .0032(17) .0161(17) -.0155(14) C1 .059(4) .071(4) .058(3) .000(3) .013(3) .002(3) C2 .053(4) .081(4) .079(4) .005(3) .008(3) -.005(3) C3 .070(4) .068(4) .089(5) -.016(3) .033(4) -.021(3) C4 .082(5) .128(7) .158(8) -.024(5) .069(5) -.031(6) C5 .099(5) .123(6) .068(4) -.013(5) .048(4) .003(4) C6 .079(4) .094(4) .049(3) .000(4) .022(3) .011(3) C7 .049(3) .042(2) .039(2) -.006(2) .014(2) -.0035(19) C8 .042(2) .040(2) .0288(18) -.0053(19) .0054(17) -.0001(17) C9 .068(3) .049(3) .036(2) -.003(2) .002(2) .004(2) C10 .079(4) .066(4) .031(2) -.015(3) .005(2) -.006(2) C11 .061(3) .056(3) .054(3) -.013(3) .013(2) -.026(2) C12 .054(3) .041(2) .057(3) -.001(2) .013(2) -.007(2) C13 .042(2) .036(2) .0335(19) -.0030(19) .0072(17) -.0002(17) C14 .044(3) .036(2) .040(2) -.0005(19) .0126(19) .0006(18) C15 .047(3) .051(3) .038(2) -.001(2) .008(2) -.0041(19) C16 .043(3) .053(3) .044(2) -.008(2) .013(2) -.007(2) C17 .041(3) .044(2) .046(2) -.002(2) .015(2) .000(2) C18 .049(3) .069(3) .062(3) -.015(3) .017(2) -.011(3) C19 .044(3) .076(4) .079(4) -.021(3) .012(3) -.003(3) C20 .052(3) .065(3) .078(4) -.009(3) .024(3) .001(3) C21 .052(3) .050(3) .058(3) .001(2) .027(2) .007(2) C22 .078(4) .085(4) .065(4) .001(3) .046(3) -.005(3) C23 .103(5) .104(5) .068(4) -.012(5) .046(4) -.030(4) C24 .081(4) .119(6) .076(4) -.029(4) .032(3) -.050(4) C25 .057(3) .079(4) .059(3) -.006(3) .028(3) -.017(3) C26 .042(3) .045(2) .043(2) -.002(2) .017(2) .0029(19) loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C .0181 .0091 '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' S S .3331 .5567 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N .0311 .0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O .0492 .0322 '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 119.7(2) yes O2 S1 N 106.2(2) yes O1 S1 N 106.1(2) yes O2 S1 C7 109.4(2) yes O1 S1 C7 107.1(2) yes N S1 C7 107.9(2) yes C13 S2 C14 91.0(2) yes C8 N C14 111.8(3) yes C8 N S1 120.1(3) no C14 N S1 119.8(3) no C7 C1 C2 120.2(5) no C7 C1 H1 119.9 no C2 C1 H1 119.9 no C3 C2 C1 121.3(6) no C3 C2 H2 119.4 no C1 C2 H2 119.4 no C5 C3 C2 117.9(6) no C5 C3 C4 120.8(7) no C2 C3 C4 121.3(7) no C3 C4 H4A 109.5 no C3 C4 H4B 109.5 no H4A C4 H4B 109.5 no C3 C4 H4C 109.5 no H4A C4 H4C 109.5 no H4B C4 H4C 109.5 no C3 C5 C6 122.6(6) no C3 C5 H5 118.7 no C6 C5 H5 118.7 no C7 C6 C5 118.9(6) no C7 C6 H6 120.6 no C5 C6 H6 120.6 no C1 C7 C6 119.2(5) no C1 C7 S1 120.2(4) no C6 C7 S1 120.6(4) no C9 C8 C13 120.8(4) no C9 C8 N 125.8(4) no C13 C8 N 113.4(3) yes C10 C9 C8 118.6(5) no C10 C9 H9 120.7 no C8 C9 H9 120.7 no C11 C10 C9 120.7(4) no C11 C10 H10 119.7 no C9 C10 H10 119.7 no C10 C11 C12 121.1(4) no C10 C11 H11 119.4 no C12 C11 H11 119.4 no C13 C12 C11 118.2(4) no C13 C12 H12 120.9 no C11 C12 H12 120.9 no C12 C13 C8 120.6(4) no C12 C13 S2 126.4(4) no C8 C13 S2 113.0(3) yes N C14 C15 110.5(4) yes N C14 S2 105.5(3) yes C15 C14 S2 112.2(3) yes N C14 H14 109.5 no C15 C14 H14 109.5 no S2 C14 H14 109.5 no C16 C15 C14 123.6(4) yes C16 C15 H15 118.2 no C14 C15 H15 118.2 no C15 C16 C17 128.6(4) yes C15 C16 H16 115.7 no C17 C16 H16 115.7 no C18 C17 C26 118.2(4) no C18 C17 C16 121.4(4) no C26 C17 C16 120.4(4) no C17 C18 C19 122.0(5) no C17 C18 H18 119.0 no C19 C18 H18 119.0 no C20 C19 C18 120.2(5) no C20 C19 H19 119.9 no C18 C19 H19 119.9 no C19 C20 C21 121.1(5) no C19 C20 H20 119.4 no C21 C20 H20 119.4 no C20 C21 C22 122.2(5) no C20 C21 C26 119.1(5) no C22 C21 C26 118.7(5) no C23 C22 C21 121.4(5) no C23 C22 H22 119.3 no C21 C22 H22 119.3 no C22 C23 C24 121.3(6) no C22 C23 H23 119.3 no C24 C23 H23 119.3 no C25 C24 C23 119.7(6) no C25 C24 H24 120.2 no C23 C24 H24 120.2 no C24 C25 C26 121.8(5) no C24 C25 H25 119.1 no C26 C25 H25 119.1 no C25 C26 C17 123.5(4) no C25 C26 C21 117.0(4) no C17 C26 C21 119.4(4) no loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_publ_flag S1 O2 1.423(3) yes S1 O1 1.426(3) yes S1 N 1.649(4) yes S1 C7 1.750(5) yes S2 C13 1.751(4) yes S2 C14 1.838(4) yes N C8 1.426(5) yes N C14 1.482(5) yes C1 C7 1.375(7) no C1 C2 1.388(7) no C1 H1 .9300 no C2 C3 1.365(9) no C2 H2 .9300 no C3 C5 1.357(9) no C3 C4 1.506(9) no C4 H4A .8987 no C4 H4B .8987 no C4 H4C .8987 no C5 C6 1.389(9) no C5 H5 .9300 no C6 C7 1.379(6) no C6 H6 .9300 no C8 C9 1.384(5) no C8 C13 1.384(6) no C9 C10 1.378(7) no C9 H9 .9300 no C10 C11 1.368(7) no C10 H10 .9300 no C11 C12 1.396(7) no C11 H11 .9300 no C12 C13 1.377(6) no C12 H12 .9300 no C14 C15 1.492(6) yes C14 H14 .9800 no C15 C16 1.297(6) yes C15 H15 .9300 no C16 C17 1.465(6) yes C16 H16 .9300 no C17 C18 1.371(6) no C17 C26 1.424(6) no C18 C19 1.403(7) no C18 H18 .9300 no C19 C20 1.349(7) no C19 H19 .9300 no C20 C21 1.392(7) no C20 H20 .9300 no C21 C22 1.425(7) no C21 C26 1.431(6) no C22 C23 1.326(8) no C22 H22 .9300 no C23 C24 1.388(8) no C23 H23 .9300 no C24 C25 1.374(7) no C24 H24 .9300 no C25 C26 1.412(7) no C25 H25 .9300 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 C10 H10 O1 3_655 .93 2.53 3.411(6) 159.1 yes C12 H12 O1 1_545 .93 2.69 3.346(6) 128.3 yes C20 H20 O2 2_545 .93 2.71 3.399(6) 131.8 yes 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 O2 S1 N C8 -169.4(3) no O1 S1 N C8 62.3(4) no C7 S1 N C8 -52.2(4) no O2 S1 N C14 -23.4(4) no O1 S1 N C14 -151.8(3) no C7 S1 N C14 93.8(3) no C7 C1 C2 C3 1.8(9) no C1 C2 C3 C5 -1.4(10) no C1 C2 C3 C4 178.6(6) no C2 C3 C5 C6 .3(11) no C4 C3 C5 C6 -179.7(7) no C3 C5 C6 C7 .4(11) no C2 C1 C7 C6 -1.0(8) no C2 C1 C7 S1 -177.9(4) no C5 C6 C7 C1 .0(9) no C5 C6 C7 S1 176.8(5) no O2 S1 C7 C1 40.1(5) no O1 S1 C7 C1 171.2(4) no N S1 C7 C1 -75.0(4) no O2 S1 C7 C6 -136.8(4) no O1 S1 C7 C6 -5.6(5) no N S1 C7 C6 108.1(5) no C14 N C8 C9 162.1(4) no S1 N C8 C9 -49.4(6) no C14 N C8 C13 -17.4(5) no S1 N C8 C13 131.0(3) no C13 C8 C9 C10 -2.7(7) no N C8 C9 C10 177.8(4) no C8 C9 C10 C11 1.2(8) no C9 C10 C11 C12 1.4(8) no C10 C11 C12 C13 -2.5(7) no C11 C12 C13 C8 1.0(7) no C11 C12 C13 S2 -179.4(4) no C9 C8 C13 C12 1.6(7) no N C8 C13 C12 -178.9(4) no C9 C8 C13 S2 -178.0(4) no N C8 C13 S2 1.5(5) no C14 S2 C13 C12 -168.6(4) no C14 S2 C13 C8 11.0(3) no C8 N C14 C15 -97.6(4) no S1 N C14 C15 113.9(4) no C8 N C14 S2 23.9(4) no S1 N C14 S2 -124.6(3) no C13 S2 C14 N -19.3(3) no C13 S2 C14 C15 101.1(3) no N C14 C15 C16 -127.0(5) no S2 C14 C15 C16 115.5(5) no C14 C15 C16 C17 177.5(4) yes C15 C16 C17 C18 4.5(8) no C15 C16 C17 C26 -174.3(5) no C26 C17 C18 C19 2.3(8) no C16 C17 C18 C19 -176.5(5) no C17 C18 C19 C20 -2.0(9) no C18 C19 C20 C21 .6(9) no C19 C20 C21 C22 -179.6(6) no C19 C20 C21 C26 .1(8) no C20 C21 C22 C23 179.4(6) no C26 C21 C22 C23 -.4(9) no C21 C22 C23 C24 .3(11) no C22 C23 C24 C25 .9(12) no C23 C24 C25 C26 -2.1(11) no C24 C25 C26 C17 -178.8(6) no C24 C25 C26 C21 2.0(8) no C18 C17 C26 C25 179.4(5) no C16 C17 C26 C25 -1.7(7) no C18 C17 C26 C21 -1.5(7) no C16 C17 C26 C21 177.4(4) no C20 C21 C26 C25 179.4(5) no C22 C21 C26 C25 -.8(7) no C20 C21 C26 C17 .3(7) no C22 C21 C26 C17 -179.9(5) no