#------------------------------------------------------------------------------ #$Date: 2025-08-19 15:49:58 +0100 (Tue, 19 Aug 2025) $ #$Revision: 301806 $ #$URL: svn://www.crystallography.net/cod/cif/2/23/90/2239052.cif $ #------------------------------------------------------------------------------ # # This file is available in the Crystallography Open Database (COD), # http://www.crystallography.net/ # # All data on this site have been placed in the public domain by the # contributors. # data_2239052 loop_ _publ_author_name 'Bunev, Alexander S.' 'Sukhonosova, Elena V.' 'Statsyuk, Vladimir E.' 'Ostapenko, Gennady I.' 'Khrustalev, Victor N.' _publ_section_title ; 7-Nitro-2-phenylimidazo[2,1-b][1,3]benzothiazole ; _journal_coeditor_code RK2421 _journal_issue 2 _journal_name_full 'Acta Crystallographica Section E' _journal_page_first o143 _journal_page_last o144 _journal_paper_doi 10.1107/S1600536814000476 _journal_volume 70 _journal_year 2014 _chemical_formula_iupac 'C15 H9 N3 O2 S' _chemical_formula_moiety 'C15 H9 N3 O2 S' _chemical_formula_sum 'C15 H9 N3 O2 S' _chemical_formula_weight 295.32 _chemical_melting_point_gt 539 _chemical_melting_point_lt 541 _chemical_name_systematic ; 7-Nitro-2-phenylimidazo[2,1-b][1,3]benzothiazole ; _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' _atom_sites_solution_hydrogens geom _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _audit_creation_method SHELXL97 _cell_angle_alpha 90.00 _cell_angle_beta 105.0770(10) _cell_angle_gamma 90.00 _cell_formula_units_Z 4 _cell_length_a 6.8068(3) _cell_length_b 21.0244(9) _cell_length_c 9.0699(4) _cell_measurement_reflns_used 6622 _cell_measurement_temperature 120(2) _cell_measurement_theta_max 32.65 _cell_measurement_theta_min 2.52 _cell_volume 1253.30(9) _computing_cell_refinement 'SAINT (Bruker, 2001)' _computing_data_collection 'APEX2 (Bruker, 2005)' _computing_data_reduction 'SAINT (Bruker, 2001)' _computing_molecular_graphics 'SHELXTL (Sheldrick, 2008)' _computing_publication_material 'SHELXTL (Sheldrick, 2008)' _computing_structure_refinement 'SHELXTL (Sheldrick, 2008)' _computing_structure_solution 'SHELXTL (Sheldrick, 2008)' _diffrn_ambient_temperature 120(2) _diffrn_measured_fraction_theta_full 0.999 _diffrn_measured_fraction_theta_max 0.999 _diffrn_measurement_device_type 'Bruker APEXII CCD' _diffrn_measurement_method '\f and \w scans' _diffrn_radiation_monochromator graphite _diffrn_radiation_source 'fine--focus sealed tube' _diffrn_radiation_type MoK\a _diffrn_radiation_wavelength 0.71073 _diffrn_reflns_av_R_equivalents 0.0406 _diffrn_reflns_av_sigmaI/netI 0.0335 _diffrn_reflns_limit_h_max 10 _diffrn_reflns_limit_h_min -10 _diffrn_reflns_limit_k_max 30 _diffrn_reflns_limit_k_min -31 _diffrn_reflns_limit_l_max 13 _diffrn_reflns_limit_l_min -13 _diffrn_reflns_number 19380 _diffrn_reflns_theta_full 32.66 _diffrn_reflns_theta_max 32.66 _diffrn_reflns_theta_min 1.94 _exptl_absorpt_coefficient_mu 0.266 _exptl_absorpt_correction_T_max 0.974 _exptl_absorpt_correction_T_min 0.924 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details '(SADABS; Bruker, 2003)' _exptl_crystal_colour yellow _exptl_crystal_density_diffrn 1.565 _exptl_crystal_density_method 'not measured' _exptl_crystal_description prism _exptl_crystal_F_000 608 _exptl_crystal_size_max 0.30 _exptl_crystal_size_mid 0.10 _exptl_crystal_size_min 0.10 _refine_diff_density_max 0.544 _refine_diff_density_min -0.382 _refine_ls_extinction_method none _refine_ls_goodness_of_fit_ref 1.026 _refine_ls_hydrogen_treatment constr _refine_ls_matrix_type full _refine_ls_number_parameters 190 _refine_ls_number_reflns 4586 _refine_ls_number_restraints 0 _refine_ls_restrained_S_all 1.026 _refine_ls_R_factor_all 0.0540 _refine_ls_R_factor_gt 0.0412 _refine_ls_shift/su_max 0.001 _refine_ls_shift/su_mean 0.000 _refine_ls_structure_factor_coef Fsqd _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.058P)^2^+0.471P] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_gt 0.1020 _refine_ls_wR_factor_ref 0.1104 _reflns_number_gt 3740 _reflns_number_total 4586 _reflns_threshold_expression I>2\s(I) _iucr_refine_instructions_details ; TITL I in P2(1)/c CELL 0.71073 6.8068 21.0244 9.0699 90.000 105.077 90.000 ZERR 4.00 0.0003 0.0009 0.0004 0.000 0.001 0.000 LATT 1 SYMM -X, 0.5+Y, 0.5-Z SFAC C H N O S UNIT 60 36 12 8 4 TEMP -153.0 SIZE 0.10 0.10 0.30 L.S. 12 BOND $H ACTA CONF WGHT 0.058000 0.471000 FVAR 0.16308 N1 3 0.285915 0.516051 0.715849 11.00000 0.01961 0.01293 = 0.01377 0.00054 0.00381 0.00078 C2 1 0.285235 0.453069 0.664324 11.00000 0.01253 0.01330 = 0.01483 0.00064 0.00367 0.00046 C3 1 0.257240 0.450887 0.508203 11.00000 0.01561 0.01235 = 0.01508 0.00035 0.00468 0.00046 AFIX 43 H3 2 0.250264 0.414169 0.446006 11.00000 -1.20000 AFIX 0 N4 3 0.241499 0.513938 0.461811 11.00000 0.01483 0.01219 = 0.01202 0.00039 0.00331 0.00094 C4A 1 0.212276 0.548328 0.327290 11.00000 0.01199 0.01294 = 0.01366 0.00119 0.00371 -0.00035 C5 1 0.192972 0.524213 0.181230 11.00000 0.01604 0.01373 = 0.01423 -0.00049 0.00492 0.00035 AFIX 43 H5 2 0.203501 0.479867 0.164699 11.00000 -1.20000 AFIX 0 C6 1 0.157928 0.566878 0.060686 11.00000 0.01594 0.01623 = 0.01343 0.00014 0.00450 -0.00016 AFIX 43 H6 2 0.144952 0.552236 -0.040490 11.00000 -1.20000 AFIX 0 C7 1 0.141923 0.631627 0.089718 11.00000 0.01403 0.01501 = 0.01357 0.00255 0.00430 0.00045 N7 3 0.092294 0.675061 -0.040627 11.00000 0.01946 0.01874 = 0.01635 0.00354 0.00627 0.00274 O1 4 0.038302 0.652105 -0.169902 11.00000 0.04477 0.02777 = 0.01293 0.00222 0.00757 0.00875 O2 4 0.103208 0.732616 -0.015622 11.00000 0.03868 0.01546 = 0.02479 0.00575 0.00756 -0.00067 C8 1 0.168501 0.657072 0.235201 11.00000 0.01586 0.01312 = 0.01566 0.00079 0.00529 -0.00032 AFIX 43 H8 2 0.162147 0.701579 0.251449 11.00000 -1.20000 AFIX 0 C8A 1 0.204848 0.613982 0.355581 11.00000 0.01455 0.01321 = 0.01305 -0.00017 0.00326 -0.00019 S9 5 0.236012 0.631304 0.550048 11.00000 0.02653 0.01152 = 0.01288 -0.00043 0.00455 0.00037 C9A 1 0.259200 0.550103 0.591077 11.00000 0.01726 0.01312 = 0.01317 -0.00098 0.00361 0.00018 C10 1 0.316348 0.399845 0.772468 11.00000 0.01274 0.01337 = 0.01519 0.00198 0.00442 0.00079 C11 1 0.371987 0.411480 0.929595 11.00000 0.01647 0.01604 = 0.01461 0.00095 0.00440 -0.00113 AFIX 43 H11 2 0.384294 0.454031 0.966091 11.00000 -1.20000 AFIX 0 C12 1 0.409571 0.361132 1.033198 11.00000 0.02053 0.02177 = 0.01527 0.00318 0.00497 -0.00113 AFIX 43 H12 2 0.447420 0.369543 1.139776 11.00000 -1.20000 AFIX 0 C13 1 0.391858 0.298634 0.981100 11.00000 0.02344 0.01801 = 0.02094 0.00683 0.00830 0.00076 AFIX 43 H13 2 0.420497 0.264365 1.051728 11.00000 -1.20000 AFIX 0 C14 1 0.331762 0.286565 0.824453 11.00000 0.02636 0.01419 = 0.02168 0.00222 0.00901 0.00092 AFIX 43 H14 2 0.316299 0.243954 0.788432 11.00000 -1.20000 AFIX 0 C15 1 0.294520 0.336623 0.721137 11.00000 0.02034 0.01438 = 0.01642 0.00087 0.00562 0.00161 AFIX 43 H15 2 0.253878 0.328011 0.614690 11.00000 -1.20000 HKLF 4 REM I in P2(1)/c REM R1 = 0.0412 for 3740 Fo > 4sig(Fo) and 0.0540 for all 4586 data REM 190 parameters refined using 0 restraints END WGHT 0.0580 0.4710 REM Highest difference peak 0.544, deepest hole -0.382, 1-sigma level 0.070 Q1 1 0.2117 0.6270 0.4575 11.00000 0.05 0.54 Q2 1 0.3448 0.4081 0.8445 11.00000 0.05 0.54 Q3 1 0.1577 0.6432 0.1657 11.00000 0.05 0.54 Q4 1 0.3691 0.2919 0.9077 11.00000 0.05 0.52 Q5 1 0.2710 0.4481 0.5918 11.00000 0.05 0.52 Q6 1 0.1441 0.5999 0.0813 11.00000 0.05 0.52 Q7 1 0.2151 0.5807 0.3441 11.00000 0.05 0.51 Q8 1 0.2142 0.5324 0.2620 11.00000 0.05 0.51 Q9 1 0.2268 0.5945 0.5737 11.00000 0.05 0.50 Q10 1 0.3152 0.3133 0.7763 11.00000 0.05 0.49 Q11 1 0.3846 0.3849 0.9757 11.00000 0.05 0.48 Q12 1 0.1875 0.6373 0.2990 11.00000 0.05 0.48 Q13 1 0.1975 0.5524 0.1335 11.00000 0.05 0.48 Q14 1 0.4185 0.3321 0.9987 11.00000 0.05 0.47 Q15 1 0.3172 0.3696 0.7482 11.00000 0.05 0.44 Q16 1 0.2271 0.5295 0.3912 11.00000 0.05 0.43 Q17 1 0.2561 0.5270 0.6468 11.00000 0.05 0.43 Q18 1 0.2468 0.5346 0.5287 11.00000 0.05 0.41 Q19 1 0.2487 0.4822 0.4837 11.00000 0.05 0.40 Q20 1 0.1918 0.6610 0.5816 11.00000 0.05 0.39 ; _cod_data_source_file rk2421sup1.cif _cod_data_source_block I _cod_original_sg_symbol_H-M 'P 21/c' _cod_database_code 2239052 _cod_database_fobs_code 2239052 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_type_symbol _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_symmetry_multiplicity N N1 0.28591(16) 0.51605(5) 0.71585(12) 0.01553(19) Uani d . 1 1 C C2 0.28524(17) 0.45307(5) 0.66432(13) 0.0135(2) Uani d . 1 1 C C3 0.25724(17) 0.45089(5) 0.50820(14) 0.0142(2) Uani d . 1 1 H H3 0.2503 0.4142 0.4460 0.017 Uiso calc R 1 1 N N4 0.24150(15) 0.51394(5) 0.46181(11) 0.01305(18) Uani d . 1 1 C C4A 0.21228(17) 0.54833(5) 0.32729(13) 0.0128(2) Uani d . 1 1 C C5 0.19297(18) 0.52421(6) 0.18123(13) 0.0145(2) Uani d . 1 1 H H5 0.2035 0.4799 0.1647 0.017 Uiso calc R 1 1 C C6 0.15793(18) 0.56688(6) 0.06069(13) 0.0151(2) Uani d . 1 1 H H6 0.1450 0.5522 -0.0405 0.018 Uiso calc R 1 1 C C7 0.14192(17) 0.63163(6) 0.08972(13) 0.0141(2) Uani d . 1 1 N N7 0.09229(16) 0.67506(5) -0.04063(12) 0.0179(2) Uani d . 1 1 O O1 0.03830(18) 0.65210(5) -0.16990(11) 0.0285(2) Uani d . 1 1 O O2 0.10321(17) 0.73262(5) -0.01562(12) 0.0264(2) Uani d . 1 1 C C8 0.16850(18) 0.65707(5) 0.23520(13) 0.0147(2) Uani d . 1 1 H H8 0.1621 0.7016 0.2514 0.018 Uiso calc R 1 1 C C8A 0.20485(17) 0.61398(6) 0.35558(13) 0.0137(2) Uani d . 1 1 S S9 0.23601(5) 0.631304(14) 0.55005(3) 0.01708(8) Uani d . 1 1 C C9A 0.25920(18) 0.55010(6) 0.59108(13) 0.0146(2) Uani d . 1 1 C C10 0.31635(17) 0.39985(5) 0.77247(13) 0.0136(2) Uani d . 1 1 C C11 0.37199(18) 0.41148(6) 0.92960(14) 0.0156(2) Uani d . 1 1 H H11 0.3843 0.4540 0.9661 0.019 Uiso calc R 1 1 C C12 0.4096(2) 0.36113(6) 1.03320(14) 0.0191(2) Uani d . 1 1 H H12 0.4474 0.3695 1.1398 0.023 Uiso calc R 1 1 C C13 0.3919(2) 0.29863(6) 0.98110(15) 0.0203(2) Uani d . 1 1 H H13 0.4205 0.2644 1.0517 0.024 Uiso calc R 1 1 C C14 0.3318(2) 0.28656(6) 0.82445(15) 0.0202(2) Uani d . 1 1 H H14 0.3163 0.2440 0.7884 0.024 Uiso calc R 1 1 C C15 0.29452(19) 0.33662(6) 0.72114(14) 0.0169(2) Uani d . 1 1 H H15 0.2539 0.3280 0.6147 0.020 Uiso calc R 1 1 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 N1 0.0196(5) 0.0129(4) 0.0138(4) 0.0008(3) 0.0038(4) 0.0005(3) C2 0.0125(5) 0.0133(5) 0.0148(5) 0.0005(4) 0.0037(4) 0.0006(4) C3 0.0156(5) 0.0124(5) 0.0151(5) 0.0005(4) 0.0047(4) 0.0003(4) N4 0.0148(4) 0.0122(4) 0.0120(4) 0.0009(3) 0.0033(3) 0.0004(3) C4A 0.0120(5) 0.0129(5) 0.0137(5) -0.0003(4) 0.0037(4) 0.0012(4) C5 0.0160(5) 0.0137(5) 0.0142(5) 0.0004(4) 0.0049(4) -0.0005(4) C6 0.0159(5) 0.0162(5) 0.0134(5) -0.0002(4) 0.0045(4) 0.0001(4) C7 0.0140(5) 0.0150(5) 0.0136(5) 0.0004(4) 0.0043(4) 0.0026(4) N7 0.0195(5) 0.0187(5) 0.0164(5) 0.0027(4) 0.0063(4) 0.0035(4) O1 0.0448(6) 0.0278(5) 0.0129(4) 0.0087(5) 0.0076(4) 0.0022(4) O2 0.0387(6) 0.0155(4) 0.0248(5) -0.0007(4) 0.0076(4) 0.0058(4) C8 0.0159(5) 0.0131(5) 0.0157(5) -0.0003(4) 0.0053(4) 0.0008(4) C8A 0.0146(5) 0.0132(5) 0.0131(5) -0.0002(4) 0.0033(4) -0.0002(4) S9 0.02653(16) 0.01152(13) 0.01288(13) 0.00037(10) 0.00455(11) -0.00043(9) C9A 0.0173(5) 0.0131(5) 0.0132(5) 0.0002(4) 0.0036(4) -0.0010(4) C10 0.0127(5) 0.0134(5) 0.0152(5) 0.0008(4) 0.0044(4) 0.0020(4) C11 0.0165(5) 0.0160(5) 0.0146(5) -0.0011(4) 0.0044(4) 0.0010(4) C12 0.0205(6) 0.0218(6) 0.0153(5) -0.0011(4) 0.0050(4) 0.0032(4) C13 0.0234(6) 0.0180(5) 0.0209(6) 0.0008(4) 0.0083(5) 0.0068(4) C14 0.0264(6) 0.0142(5) 0.0217(6) 0.0009(4) 0.0090(5) 0.0022(4) C15 0.0203(5) 0.0144(5) 0.0164(5) 0.0016(4) 0.0056(4) 0.0009(4) loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' S S 0.1246 0.1234 '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 C9A N1 C2 103.89(10) C3 C2 N1 111.14(10) C3 C2 C10 128.20(11) N1 C2 C10 120.64(10) C2 C3 N4 105.00(10) C2 C3 H3 127.5 N4 C3 H3 127.5 C9A N4 C3 106.68(10) C9A N4 C4A 114.97(10) C3 N4 C4A 138.35(10) N4 C4A C5 127.12(10) N4 C4A C8A 110.77(10) C5 C4A C8A 122.12(10) C6 C5 C4A 117.98(11) C6 C5 H5 121.0 C4A C5 H5 121.0 C5 C6 C7 119.22(11) C5 C6 H6 120.4 C7 C6 H6 120.4 C8 C7 C6 123.81(11) C8 C7 N7 118.19(10) C6 C7 N7 118.00(10) O2 N7 O1 123.34(11) O2 N7 C7 118.37(11) O1 N7 C7 118.28(11) C8A C8 C7 116.54(11) C8A C8 H8 121.7 C7 C8 H8 121.7 C8 C8A C4A 120.22(11) C8 C8A S9 127.08(9) C4A C8A S9 112.66(9) C9A S9 C8A 89.54(5) N1 C9A N4 113.29(10) N1 C9A S9 134.63(9) N4 C9A S9 112.07(8) C11 C10 C15 118.77(11) C11 C10 C2 120.14(10) C15 C10 C2 121.09(11) C12 C11 C10 120.52(11) C12 C11 H11 119.7 C10 C11 H11 119.7 C13 C12 C11 120.25(12) C13 C12 H12 119.9 C11 C12 H12 119.9 C12 C13 C14 119.61(12) C12 C13 H13 120.2 C14 C13 H13 120.2 C15 C14 C13 120.21(12) C15 C14 H14 119.9 C13 C14 H14 119.9 C14 C15 C10 120.61(11) C14 C15 H15 119.7 C10 C15 H15 119.7 loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance N1 C9A 1.3112(15) N1 C2 1.4038(15) C2 C3 1.3795(16) C2 C10 1.4666(16) C3 N4 1.3865(15) C3 H3 0.9500 N4 C9A 1.3761(15) N4 C4A 1.3873(14) C4A C5 1.3924(16) C4A C8A 1.4073(16) C5 C6 1.3861(16) C5 H5 0.9500 C6 C7 1.3962(17) C6 H6 0.9500 C7 C8 1.3913(16) C7 N7 1.4621(15) N7 O2 1.2298(15) N7 O1 1.2323(15) C8 C8A 1.3905(16) C8 H8 0.9500 C8A S9 1.7590(12) S9 C9A 1.7457(12) C10 C11 1.3977(16) C10 C15 1.4034(16) C11 C12 1.3942(17) C11 H11 0.9500 C12 C13 1.3909(19) C12 H12 0.9500 C13 C14 1.3957(19) C13 H13 0.9500 C14 C15 1.3880(17) C14 H14 0.9500 C15 H15 0.9500 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 C9A N1 C2 C3 -0.18(13) C9A N1 C2 C10 178.54(10) N1 C2 C3 N4 0.39(13) C10 C2 C3 N4 -178.21(11) C2 C3 N4 C9A -0.43(12) C2 C3 N4 C4A -179.63(13) C9A N4 C4A C5 178.88(11) C3 N4 C4A C5 -2.0(2) C9A N4 C4A C8A -0.78(14) C3 N4 C4A C8A 178.38(13) N4 C4A C5 C6 177.96(11) C8A C4A C5 C6 -2.41(17) C4A C5 C6 C7 -0.48(17) C5 C6 C7 C8 3.11(18) C5 C6 C7 N7 -176.24(10) C8 C7 N7 O2 9.70(17) C6 C7 N7 O2 -170.91(11) C8 C7 N7 O1 -169.09(11) C6 C7 N7 O1 10.30(16) C6 C7 C8 C8A -2.66(17) N7 C7 C8 C8A 176.69(10) C7 C8 C8A C4A -0.31(17) C7 C8 C8A S9 -177.77(9) N4 C4A C8A C8 -177.46(10) C5 C4A C8A C8 2.86(17) N4 C4A C8A S9 0.33(12) C5 C4A C8A S9 -179.35(9) C8 C8A S9 C9A 177.73(11) C4A C8A S9 C9A 0.12(9) C2 N1 C9A N4 -0.11(14) C2 N1 C9A S9 178.45(11) C3 N4 C9A N1 0.36(14) C4A N4 C9A N1 179.77(10) C3 N4 C9A S9 -178.54(8) C4A N4 C9A S9 0.88(13) C8A S9 C9A N1 -179.12(13) C8A S9 C9A N4 -0.55(9) C3 C2 C10 C11 170.54(12) N1 C2 C10 C11 -7.93(17) C3 C2 C10 C15 -8.38(18) N1 C2 C10 C15 173.14(11) C15 C10 C11 C12 1.45(17) C2 C10 C11 C12 -177.50(11) C10 C11 C12 C13 -0.06(19) C11 C12 C13 C14 -1.4(2) C12 C13 C14 C15 1.5(2) C13 C14 C15 C10 -0.10(19) C11 C10 C15 C14 -1.37(18) C2 C10 C15 C14 177.57(11) loop_ _cod_related_entry_id _cod_related_entry_database _cod_related_entry_code 1 PubChem 19209665