#------------------------------------------------------------------------------ #$Date: 2025-08-18 23:52:38 +0100 (Mon, 18 Aug 2025) $ #$Revision: 301791 $ #$URL: svn://www.crystallography.net/cod/cif/2/00/32/2003249.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_2003249 loop_ _publ_author_name 'Jasinski, J. P.' 'Paight, E. S.' _publ_contact_author ; Dr. Jerry P. Jasinski Chemistry Department Keene State College 229 Main St. Keene, New Hampshire 03431 USA ; _publ_section_title ; 3-(2-Benzothiazolyl)-7-(diethylamino)coumarin ; _journal_issue 3 _journal_name_full 'Acta Crystallographica Section C' _journal_page_first 531 _journal_page_last 533 _journal_paper_doi 10.1107/S0108270194003628 _journal_volume 51 _journal_year 1995 _chemical_compound_source 'Sigma Chemical Co.,St. Louis, Mo.,USA' _chemical_formula_sum 'C20 H18 N2 O2 S' _chemical_formula_weight 350.43 _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 'from TEXRAY.INF file' _cell_angle_alpha 95.14(1) _cell_angle_beta 104.50(1) _cell_angle_gamma 86.74(1) _cell_formula_units_Z 2 _cell_length_a 8.962(1) _cell_length_b 11.136(2) _cell_length_c 8.922(1) _cell_measurement_reflns_used 25 _cell_measurement_temperature 296.0 _cell_measurement_theta_max 49.37 _cell_measurement_theta_min 42.38 _cell_volume 858.0(2) _computing_cell_refinement 'MSC/AFC Diffractometer Control Software' _computing_data_collection ;MSC/AFC Diffractometer Control Software (Molecular Structure Corporation, 1988) ; _computing_data_reduction 'TEXSAN: PROCESS (Molecular Structure Corporation, 1985)' _computing_publication_material 'TEXSAN: FINISH' _computing_structure_refinement 'TEXSAN: LS' _computing_structure_solution 'MITHRIL (Gilmore, 1984)' _diffrn_ambient_temperature 296.0 _diffrn_measurement_device AFC6S _diffrn_measurement_method '\w/2\q scans (speed 8.0\% min^-1^ in \w)' _diffrn_radiation_monochromator graphite _diffrn_radiation_source 'X-ray tube' _diffrn_radiation_type MoK\a _diffrn_radiation_wavelength 0.7107 _diffrn_reflns_av_R_equivalents 0.022 _diffrn_reflns_limit_h_max 11 _diffrn_reflns_limit_h_min 0 _diffrn_reflns_limit_k_max 13 _diffrn_reflns_limit_k_min -13 _diffrn_reflns_limit_l_max 11 _diffrn_reflns_limit_l_min -11 _diffrn_reflns_number 3226 _diffrn_reflns_theta_max 25 _diffrn_reflns_theta_min 5.000 _diffrn_standards_decay_% -0.60 _diffrn_standards_interval_count 150 _diffrn_standards_number 3 _exptl_absorpt_coefficient_mu 0.1945 _exptl_absorpt_correction_T_max 1.000 _exptl_absorpt_correction_T_min 0.981 _exptl_absorpt_correction_type 'empirical (\y scans)' _exptl_absorpt_process_details \y-scan _exptl_crystal_colour orange _exptl_crystal_density_diffrn 1.356 _exptl_crystal_description needle _exptl_crystal_F_000 368.00 _exptl_crystal_size_max 1.00 _exptl_crystal_size_mid 0.20 _exptl_crystal_size_min 0.20 _refine_diff_density_max 0.16 _refine_diff_density_min -0.22 _refine_ls_extinction_coef 1.2790E-6(1) _refine_ls_extinction_method ' Type 2, Gaussian, isotropic (Zachariasen, 1963)' _refine_ls_goodness_of_fit_obs 1.528 _refine_ls_hydrogen_treatment refall _refine_ls_matrix_type full _refine_ls_number_parameters 299 _refine_ls_number_reflns 2123 _refine_ls_number_restraints 0 _refine_ls_R_factor_obs 0.0359 _refine_ls_shift/esd_max 0.4404 _refine_ls_structure_factor_coef F _refine_ls_weighting_details 'w = 4F~o~^2^/\s^2^(F~o~^2^) where \s(F^2^) = [S^2^(C + 4B) + (\rF~o~^2^)^2^]' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_obs 0.0413 _reflns_number_observed 2123 _reflns_number_total 3010 _reflns_observed_criterion I>3.0\s(I) _cod_data_source_file cd1034.cif _cod_data_source_block cd1034a _cod_depositor_comments ; The following automatic conversions were performed: '_refine_ls_weighting_scheme' value 'w = 4F~o~^2^/\s^2^(F~o~^2^) where \s(F^2^) = [S^2^(C + 4B) + (\rF~o~^2^)^2^]' was changed to 'calc'. New tag '_refine_ls_weighting_details' was created. The value of the new tag was set to 'w = 4F~o~^2^/\s^2^(F~o~^2^) where \s(F^2^) = [S^2^(C + 4B) + (\rF~o~^2^)^2^]'. Automatic conversion script Id: cif_fix_values 3143 2015-03-26 13:38:13Z robertas ; _cod_original_formula_sum 'C20 H18 N2 O2 S1' _cod_database_code 2003249 loop_ _symmetry_equiv_pos_as_xyz ' +x, +y, +z' ' -x, -y, -z' loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_12 _atom_site_aniso_U_13 _atom_site_aniso_U_22 _atom_site_aniso_U_23 _atom_site_aniso_U_33 S1' 0.0475(3) -0.0035(2) 0.0062(2) 0.0443(3) -0.0053(2) 0.0366(2) O1 0.0483(7) -0.0010(6) 0.0033(6) 0.0353(7) -0.0074(5) 0.0328(6) O11 0.0602(9) 0.0001(7) -0.0037(7) 0.0517(8) -0.0143(6) 0.0403(8) N3' 0.0418(8) -0.0009(7) 0.0097(7) 0.0415(9) -0.0028(7) 0.0362(8) N12 0.0471(9) 0.0006(7) 0.0064(7) 0.0380(9) -0.0007(7) 0.0414(9) C2 0.044(1) -0.0084(9) 0.0115(8) 0.037(1) -0.0038(8) 0.0376(10) C2' 0.0408(10) -0.0097(8) 0.0132(8) 0.039(1) -0.0026(8) 0.0329(9) C3 0.0357(9) -0.0054(8) 0.0107(7) 0.0351(10) -0.0004(8) 0.0320(9) C4 0.0424(10) -0.0071(8) 0.0158(8) 0.034(1) -0.0051(8) 0.0365(9) C4' 0.052(1) 0.0008(10) 0.0178(9) 0.047(1) -0.0028(10) 0.047(1) C5 0.049(1) -0.0045(9) 0.0109(8) 0.033(1) -0.0073(8) 0.0355(9) C5' 0.059(1) 0.009(1) 0.025(1) 0.046(1) 0.006(1) 0.060(1) C6 0.044(1) -0.0079(9) 0.0045(8) 0.044(1) -0.0042(9) 0.0341(10) C6' 0.048(1) 0.007(1) 0.013(1) 0.060(1) 0.017(1) 0.056(1) C7 0.0400(10) -0.0073(8) 0.0124(8) 0.0344(10) -0.0002(8) 0.0385(10) C7' 0.049(1) -0.003(1) 0.0079(9) 0.059(1) 0.006(1) 0.043(1) C8 0.045(1) -0.0026(8) 0.0126(8) 0.0317(10) -0.0047(8) 0.0381(10) C8' 0.0404(10) -0.0027(9) 0.0131(8) 0.041(1) 0.0022(8) 0.041(1) C9 0.0388(9) -0.0109(8) 0.0096(7) 0.0376(10) -0.0025(8) 0.0299(9) C9' 0.0403(10) -0.0049(9) 0.0141(8) 0.043(1) 0.0019(8) 0.0369(9) C10 0.0401(10) -0.0054(8) 0.0115(7) 0.0308(9) -0.0033(7) 0.0317(9) C13 0.051(1) 0.0047(10) 0.0148(10) 0.043(1) -0.0002(9) 0.049(1) C14 0.058(1) -0.001(1) -0.003(1) 0.046(1) 0.0017(10) 0.049(1) C15 0.097(2) -0.010(1) 0.038(1) 0.041(1) -0.009(1) 0.086(2) C16 0.126(2) -0.020(2) 0.011(2) 0.075(2) 0.007(1) 0.046(1) loop_ _atom_site_label _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_thermal_displace_type S1' 0.53462(6) 0.44911(5) 0.30382(6) 0.0440 Uij O1 0.1364(1) 0.69047(10) 0.0719(1) 0.0406 Uij O11 0.3324(2) 0.6513(1) 0.2674(2) 0.0548 Uij N3' 0.4428(2) 0.3225(1) 0.0409(2) 0.0402 Uij N12 -0.2867(2) 0.8045(1) -0.3372(2) 0.0433 Uij C2 0.2597(2) 0.6171(2) 0.1396(2) 0.0395 Uij C2' 0.4139(2) 0.4225(2) 0.1172(2) 0.0369 Uij C3 0.2872(2) 0.5054(2) 0.0509(2) 0.0339 Uij C4 0.1928(2) 0.4778(2) -0.0911(2) 0.0369 Uij C4' 0.6247(2) 0.1473(2) 0.0813(2) 0.0483 Uij C5 -0.0316(2) 0.5341(2) -0.3049(2) 0.0396 Uij C5' 0.7455(2) 0.0930(2) 0.1816(3) 0.0539 Uij C6 -0.1461(2) 0.6146(2) -0.3637(2) 0.0416 Uij C6' 0.8087(2) 0.1470(2) 0.3288(3) 0.0542 Uij C7 -0.1714(2) 0.7251(2) -0.2778(2) 0.0371 Uij C7' 0.7525(2) 0.2567(2) 0.3787(2) 0.0507 Uij C8 -0.0716(2) 0.7457(2) -0.1296(2) 0.0383 Uij C8' 0.6303(2) 0.3127(2) 0.2767(2) 0.0401 Uij C9 0.0432(2) 0.6633(2) -0.0743(2) 0.0352 Uij C9' 0.5657(2) 0.2585(2) 0.1285(2) 0.0391 Uij C10 0.0694(2) 0.5552(2) -0.1583(2) 0.0339 Uij C13 -0.3096(2) 0.9190(2) -0.2511(2) 0.0478 Uij C14 -0.3823(3) 0.7855(2) -0.4955(2) 0.0540 Uij C15 -0.2044(3) 1.0165(2) -0.2631(3) 0.0725 Uij C16 -0.3058(4) 0.8155(3) -0.6189(3) 0.0830 Uij H4 0.211(2) 0.400(1) -0.146(2) 0.036(5) Uij H4' 0.583(2) 0.108(2) -0.014(2) 0.064(6) Uij H5 -0.017(2) 0.462(2) -0.362(2) 0.048(5) Uij H5' 0.788(2) 0.015(2) 0.152(2) 0.053(6) Uij H6 -0.212(2) 0.596(2) -0.460(2) 0.054(6) Uij H6' 0.893(2) 0.111(2) 0.399(2) 0.053(6) Uij H7' 0.792(2) 0.298(2) 0.481(2) 0.058(6) Uij H8 -0.083(2) 0.819(1) -0.069(2) 0.038(5) Uij H13A -0.419(2) 0.944(2) -0.286(2) 0.060(6) Uij H13B -0.303(2) 0.904(2) -0.142(2) 0.051(5) Uij H14B -0.410(2) 0.701(2) -0.514(2) 0.050(5) Uij H15A -0.222(3) 1.035(2) -0.366(3) 0.108(9) Uij H15B -0.224(3) 1.084(2) -0.210(3) 0.100(9) Uij H15C -0.094(3) 0.994(2) -0.227(3) 0.112(9) Uij H16A -0.293(3) 0.895(2) -0.611(3) 0.111(9) Uij H16B -0.367(3) 0.789(2) -0.719(3) 0.101(8) Uij H16C -0.201(3) 0.778(2) -0.606(3) 0.084(8) Uij H14A -0.479(2) 0.835(2) -0.500(2) 0.080(7) Uij loop_ _atom_type_symbol _atom_type_scat_source _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag C 'International Tables' 0.002 0.002 H 'International Tables' 0.000 0.000 O 'International Tables' 0.008 0.006 N 'International Tables' 0.004 0.003 S 'International Tables' 0.110 0.124 loop_ _diffrn_standard_refln_index_h _diffrn_standard_refln_index_k _diffrn_standard_refln_index_l 3 -2 -1 4 -2 -1 2 4 1 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 C2' S1' C8' 88.81(9) yes C2 O1 C9 122.90(10) yes C2' N3' C9' 110.80(10) yes C7 N12 C13 121.00(10) yes C7 N12 C14 121.6(2) yes C13 N12 C14 117.1(2) yes O1 C2 O11 116.4(2) yes O1 C2 C3 117.00(10) yes O11 C2 C3 126.6(2) yes S1' C2' N3' 115.60(10) yes S1' C2' C3 122.90(10) yes N3' C2' C3 121.5(2) yes C2 C3 C2' 119.70(10) yes C2 C3 C4 119.7(2) yes C2' C3 C4 120.5(2) yes C3 C4 C10 122.0(2) yes C5' C4' C9' 119.0(2) yes C6 C5 C10 122.1(2) yes C4' C5' C6' 121.1(2) yes C5 C6 C7 121.5(2) yes C5' C6' C7' 121.2(2) yes N12 C7 C6 121.1(2) yes N12 C7 C8 122.5(2) yes C6 C7 C8 116.4(2) yes C6' C7' C8' 117.9(2) yes C7 C8 C9 120.6(2) yes S1' C8' C7' 129.2(2) yes S1' C8' C9' 109.70(10) yes C7' C8' C9' 121.1(2) yes O1 C9 C8 117.0(2) yes O1 C9 C10 119.7(2) yes C8 C9 C10 123.3(2) yes N3' C9' C4' 125.2(2) yes N3' C9' C8' 115.1(2) yes C4' C9' C8' 119.7(2) yes C4 C10 C5 125.5(2) yes C4 C10 C9 118.5(2) yes C5 C10 C9 116.0(2) yes N12 C13 C15 114.6(2) yes N12 C14 C16 114.2(2) yes loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_publ_flag S1' C2' 1.754(2) yes S1' C8' 1.730(2) yes O1 C2 1.380(2) yes O1 C9 1.379(2) yes O11 C2 1.204(2) yes N3' C2' 1.300(2) yes N3' C9' 1.382(2) yes N12 C7 1.355(2) yes N12 C13 1.460(2) yes N12 C14 1.461(2) yes C2 C3 1.456(2) yes C2' C3 1.461(2) yes C3 C4 1.356(2) yes C4 C10 1.406(2) yes C4' C5' 1.369(3) yes C4' C9' 1.391(3) yes C5 C6 1.357(2) yes C5 C10 1.401(2) yes C5' C6' 1.390(3) yes C6 C7 1.428(2) yes C6' C7' 1.375(3) yes C7 C8 1.406(2) yes C7' C8' 1.393(3) yes C8 C9 1.365(2) yes C8' C9' 1.400(2) yes C9 C10 1.400(2) yes C13 C15 1.505(3) yes C14 C16 1.504(4) yes loop_ _cod_related_entry_id _cod_related_entry_database _cod_related_entry_code 1 PubChem 100334