#------------------------------------------------------------------------------ #$Date: 2026-06-05 20:28:14 +0100 (Fri, 05 Jun 2026) $ #$Revision: 306471 $ #$URL: svn://www.crystallography.net/cod/cif/7/06/44/7064408.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_7064408 loop_ _publ_author_name 'Jebbari, Said' 'Omari, Mohamed' 'Fouad, Mohammed Riad' 'Mohammad-Salim, Haydar' 'Alaqarbeh, Marwa' 'Ben Ahmed, Ali' 'Tounsi, Abdessamad' 'Harrad, Mohamed Anouar' _publ_section_title ; Synthesis and multiscale computational analysis of 6-nitrobenzoxazole-2-thione: electronic structure, intermolecular interactions, and predicted protease inhibition ; _journal_issue 20 _journal_name_full 'New Journal of Chemistry' _journal_page_first 8856 _journal_page_last 8867 _journal_paper_doi 10.1039/D6NJ00979D _journal_volume 50 _journal_year 2026 _chemical_formula_moiety 'C7 H4 N2 O3 S' _chemical_formula_sum 'C7 H4 N2 O3 S' _chemical_formula_weight 196.18 _space_group_IT_number 14 _space_group_name_Hall '-P 2yn' _space_group_name_H-M_alt 'P 1 21/n 1' _symmetry_cell_setting monoclinic _symmetry_Int_Tables_number 14 _symmetry_space_group_name_Hall '-P 2yn' _symmetry_space_group_name_H-M 'P 1 21/n 1' _atom_sites_solution_hydrogens mixed _atom_sites_solution_primary dual _atom_sites_solution_secondary dual _audit_conform_dict_location ftp://ftp.iucr.org/pub/cif_core.dic _audit_conform_dict_name cif_core.dic _audit_conform_dict_version 2.4.5 _audit_creation_date 2025-06-06T12:45:55-00:00 _audit_creation_method 'WinGX routine CIF_UPDATE' _audit_update_record ; 2026-03-16 deposited with the CCDC. 2026-04-17 downloaded from the CCDC. ; _cell_angle_alpha 90 _cell_angle_beta 98.719(2) _cell_angle_gamma 90 _cell_formula_units_Z 4 _cell_length_a 4.5721(2) _cell_length_b 15.6411(7) _cell_length_c 10.7748(5) _cell_measurement_reflns_used 9936 _cell_measurement_temperature 100(2) _cell_measurement_theta_max 28.30 _cell_measurement_theta_min 2.60 _cell_measurement_wavelength 0.71073 _cell_volume 761.63(6) _computing_cell_refinement 'SAINT V8.40B (Bruker AXS LLC, 2019)' _computing_data_collection 'APPEX5v2023.9-2 (BRUKER AXS, 2021-2023)' _computing_data_reduction 'SAINT V8.40B (Bruker AXS LLC, 2019)' _computing_molecular_graphics 'Ortep for Windows (Farrugia, 2012)' _computing_publication_material 'WinGX publication routines (Farrugia, 2012)' _computing_structure_refinement 'SHELXL-2019/2 (Sheldrick, 2019)' _computing_structure_solution 'SHELXT 2018/2 (Sheldrick, 2018)' _diffrn_ambient_temperature 100(2) _diffrn_detector 'APEX-II CCD' _diffrn_measured_fraction_theta_full 1 _diffrn_measured_fraction_theta_max 1 _diffrn_measurement_device '\k-geometry diffractometer' _diffrn_measurement_device_type 'Bruker APEX-II' _diffrn_measurement_method '\f or \w oscillation scans' _diffrn_radiation_monochromator graphite _diffrn_radiation_probe x-ray _diffrn_radiation_type MoK\a _diffrn_radiation_wavelength 0.71073 _diffrn_reflns_av_R_equivalents 0.0378 _diffrn_reflns_av_unetI/netI 0.0196 _diffrn_reflns_Laue_measured_fraction_full 1 _diffrn_reflns_Laue_measured_fraction_max 1 _diffrn_reflns_limit_h_max 6 _diffrn_reflns_limit_h_min -6 _diffrn_reflns_limit_k_max 20 _diffrn_reflns_limit_k_min -20 _diffrn_reflns_limit_l_max 14 _diffrn_reflns_limit_l_min -14 _diffrn_reflns_number 17343 _diffrn_reflns_point_group_measured_fraction_full 1 _diffrn_reflns_point_group_measured_fraction_max 1 _diffrn_reflns_theta_full 25.242 _diffrn_reflns_theta_max 28.316 _diffrn_reflns_theta_min 2.314 _exptl_absorpt_coefficient_mu 0.395 _exptl_absorpt_correction_T_max 0.9775 _exptl_absorpt_correction_T_min 0.4863 _exptl_absorpt_process_details 'BRUKER SADABS-2016/2' _exptl_crystal_colour Colourless _exptl_crystal_density_diffrn 1.711 _exptl_crystal_density_method 'not measured' _exptl_crystal_description needle _exptl_crystal_F_000 400 _exptl_crystal_size_max 0.14 _exptl_crystal_size_mid 0.12 _exptl_crystal_size_min 0.08 _refine_diff_density_max 0.368 _refine_diff_density_min -0.317 _refine_diff_density_rms 0.09 _refine_ls_extinction_method none _refine_ls_goodness_of_fit_ref 1.104 _refine_ls_hydrogen_treatment mixed _refine_ls_matrix_type full _refine_ls_number_constraints 0 _refine_ls_number_parameters 121 _refine_ls_number_reflns 1892 _refine_ls_number_restraints 0 _refine_ls_restrained_S_all 1.104 _refine_ls_R_factor_all 0.0359 _refine_ls_R_factor_gt 0.0273 _refine_ls_shift/su_max 0.001 _refine_ls_shift/su_mean 0 _refine_ls_structure_factor_coef Fsqd _refine_ls_weighting_details 'w=1/[\s^2^(Fo^2^)+(0.0427P)^2^+0.2733P] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_gt 0.0759 _refine_ls_wR_factor_ref 0.0785 _reflns_Friedel_coverage 0 _reflns_number_gt 1710 _reflns_number_total 1892 _reflns_threshold_expression 'I > 2\s(I)' _cod_data_source_file d6nj00979d1.cif _cod_data_source_block JS4 _cod_depositor_comments 'Adding full bibliography for 7064408.cif.' _cod_original_sg_symbol_H-M 'P 21/n' _cod_database_code 7064408 _shelx_estimated_absorpt_t_min 0.947 _shelx_estimated_absorpt_t_max 0.969 _shelx_shelxl_version_number 2019/3 _shelx_res_file ; TITL mo_JS4_0m_a.res in P2(1)/n mo_JS4_0m.res created by SHELXL-2019/3 at 12:43:17 on 06-Jun-2025 CELL 0.71073 4.5721 15.6411 10.7748 90.000 98.719 90.000 ZERR 2.00 0.0002 0.0007 0.0005 0.000 0.002 0.000 LATT 1 SYMM 1/2 - X, 1/2 + Y, 1/2 - Z SFAC C H N S O UNIT 28 16 8 4 12 MERG 2 EQIV $1 -x+3/2, y+1/2, -z+3/2 HTAB N2 O1_$1 HTAB N2 O2_$1 EQIV $2 -x, -y+1, -z+1 HTAB C3 S1_$2 HTAB C6 O1_$1 FMAP 2 PLAN 10 SIZE 0.14 0.12 0.08 ACTA HTAB 2.00000 BOND $H CONF LIST 4 WPDB -2 L.S. 10 TEMP -173.15 WGHT 0.0427 0.2733 FVAR 0.66577 S1 4 -0.182876 0.727352 0.484913 11.00000 0.01820 0.01659 = 0.02295 0.00373 -0.00070 0.00202 O1 5 0.741840 0.333561 0.731270 11.00000 0.04350 0.01517 = 0.02838 -0.00347 -0.00679 0.00800 O2 5 1.098118 0.392378 0.856133 11.00000 0.01946 0.02168 = 0.04018 0.00908 -0.00235 0.00366 O3 5 0.119027 0.587834 0.559129 11.00000 0.01852 0.01176 = 0.01952 -0.00018 -0.00201 0.00073 N2 3 0.281259 0.701521 0.669281 11.00000 0.01585 0.01046 = 0.02064 -0.00043 0.00048 -0.00054 N3 3 0.861693 0.396305 0.784653 11.00000 0.02244 0.01674 = 0.01958 0.00427 0.00448 0.00442 C1 1 0.077392 0.674289 0.573464 11.00000 0.01647 0.01290 = 0.01893 0.00052 0.00393 -0.00073 C7 1 0.462942 0.634806 0.716596 11.00000 0.01533 0.01220 = 0.01870 0.00041 0.00355 -0.00035 C2 1 0.356800 0.563589 0.646850 11.00000 0.01475 0.01425 = 0.01505 0.00071 0.00106 -0.00056 C3 1 0.475812 0.483268 0.665515 11.00000 0.01999 0.01250 = 0.01760 -0.00065 0.00289 -0.00012 AFIX 43 H3 2 0.399647 0.434807 0.618137 11.00000 -1.20000 AFIX 0 C4 1 0.718767 0.479441 0.760439 11.00000 0.01808 0.01290 = 0.01902 0.00342 0.00426 0.00310 C5 1 0.833946 0.549074 0.832016 11.00000 0.01624 0.01871 = 0.01870 0.00184 0.00137 -0.00060 AFIX 43 H5 2 1.001498 0.541841 0.894993 11.00000 -1.20000 AFIX 0 C6 1 0.704257 0.629207 0.811529 11.00000 0.01789 0.01526 = 0.01992 -0.00143 0.00034 -0.00225 AFIX 43 H6 2 0.776843 0.677605 0.859912 11.00000 -1.20000 AFIX 0 H2 2 0.307652 0.754659 0.684572 11.00000 -1.20000 HKLF 4 REM mo_JS4_0m_a.res in P2(1)/n REM wR2 = 0.0785, GooF = S = 1.104, Restrained GooF = 1.104 for all data REM R1 = 0.0273 for 1710 Fo > 4sig(Fo) and 0.0359 for all 1892 data REM 121 parameters refined using 0 restraints END WGHT 0.0427 0.2733 REM Instructions for potential hydrogen bonds HTAB C3 S1_$2 HTAB C6 O1_$1 HTAB N2 O1_$1 HTAB N2 O2_$1 HTAB N2 N3_$1 REM Highest difference peak 0.368, deepest hole -0.317, 1-sigma level 0.090 Q1 1 0.4113 0.5986 0.6838 11.00000 0.05 0.37 Q2 1 0.7455 0.5853 0.8291 11.00000 0.05 0.28 Q3 1 0.3635 0.6707 0.7021 11.00000 0.05 0.27 Q4 1 0.5841 0.6347 0.7672 11.00000 0.05 0.27 Q5 1 -0.3349 0.7259 0.5463 11.00000 0.05 0.26 Q6 1 0.7749 0.4425 0.7704 11.00000 0.05 0.25 Q7 1 0.4024 0.5218 0.6577 11.00000 0.05 0.25 Q8 1 0.7597 0.5132 0.8004 11.00000 0.05 0.24 Q9 1 0.1511 0.6853 0.6429 11.00000 0.05 0.23 Q10 1 0.8801 0.3588 0.7157 11.00000 0.05 0.22 ; _shelx_res_checksum 57373 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_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_site_symmetry_order _atom_site_calc_flag _atom_site_refinement_flags_posn _atom_site_refinement_flags_adp _atom_site_refinement_flags_occupancy _atom_site_disorder_assembly _atom_site_disorder_group S1 S -0.18288(7) 0.72735(2) 0.48491(3) 0.01964(11) Uani 1 1 d . . . . . O1 O 0.7418(2) 0.33356(6) 0.73127(9) 0.0303(2) Uani 1 1 d . . . . . O2 O 1.0981(2) 0.39238(6) 0.85613(10) 0.0278(2) Uani 1 1 d . . . . . O3 O 0.11903(19) 0.58783(5) 0.55913(8) 0.01711(19) Uani 1 1 d . . . . . N2 N 0.2813(2) 0.70152(6) 0.66928(9) 0.0159(2) Uani 1 1 d . . . . . N3 N 0.8617(2) 0.39631(7) 0.78465(9) 0.0195(2) Uani 1 1 d . . . . . C1 C 0.0774(3) 0.67429(7) 0.57346(11) 0.0160(2) Uani 1 1 d . . . . . C7 C 0.4629(3) 0.63481(7) 0.71660(11) 0.0153(2) Uani 1 1 d . . . . . C2 C 0.3568(3) 0.56359(7) 0.64685(10) 0.0148(2) Uani 1 1 d . . . . . C3 C 0.4758(3) 0.48327(7) 0.66551(11) 0.0167(2) Uani 1 1 d . . . . . H3 H 0.399647 0.434807 0.618137 0.02 Uiso 1 1 calc R U . . . C4 C 0.7188(3) 0.47944(7) 0.76044(11) 0.0165(2) Uani 1 1 d . . . . . C5 C 0.8339(3) 0.54907(8) 0.83202(11) 0.0180(2) Uani 1 1 d . . . . . H5 H 1.001498 0.541841 0.894993 0.022 Uiso 1 1 calc R U . . . C6 C 0.7043(3) 0.62921(8) 0.81153(11) 0.0179(2) Uani 1 1 d . . . . . H6 H 0.776843 0.677605 0.859912 0.022 Uiso 1 1 calc R U . . . H2 H 0.308(4) 0.7547(11) 0.6846(15) 0.022 Uiso 1 1 d . U . . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 S1 0.01820(17) 0.01659(16) 0.02295(17) 0.00373(10) -0.00070(11) 0.00202(11) O1 0.0435(6) 0.0152(4) 0.0284(5) -0.0035(4) -0.0068(4) 0.0080(4) O2 0.0195(5) 0.0217(5) 0.0402(5) 0.0091(4) -0.0023(4) 0.0037(4) O3 0.0185(4) 0.0118(4) 0.0195(4) -0.0002(3) -0.0020(3) 0.0007(3) N2 0.0159(5) 0.0105(5) 0.0206(5) -0.0004(4) 0.0005(4) -0.0005(4) N3 0.0224(5) 0.0167(5) 0.0196(5) 0.0043(4) 0.0045(4) 0.0044(4) C1 0.0165(5) 0.0129(5) 0.0189(5) 0.0005(4) 0.0039(4) -0.0007(4) C7 0.0153(5) 0.0122(5) 0.0187(5) 0.0004(4) 0.0036(4) -0.0003(4) C2 0.0148(5) 0.0142(5) 0.0150(5) 0.0007(4) 0.0011(4) -0.0006(4) C3 0.0200(6) 0.0125(5) 0.0176(5) -0.0006(4) 0.0029(4) -0.0001(4) C4 0.0181(6) 0.0129(5) 0.0190(5) 0.0034(4) 0.0043(4) 0.0031(4) C5 0.0162(6) 0.0187(6) 0.0187(5) 0.0018(4) 0.0014(4) -0.0006(4) C6 0.0179(6) 0.0153(5) 0.0199(5) -0.0014(4) 0.0003(4) -0.0023(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 0 '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' S S 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.006 '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_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C1 O3 C2 107.49(9) . . ? C1 N2 C7 110.51(10) . . ? C1 N2 H2 121.1(11) . . ? C7 N2 H2 127.3(11) . . ? O1 N3 O2 122.85(11) . . ? O1 N3 C4 118.25(10) . . ? O2 N3 C4 118.89(11) . . ? N2 C1 O3 107.71(10) . . ? N2 C1 S1 130.03(9) . . ? O3 C1 S1 122.26(9) . . ? N2 C7 C6 133.25(11) . . ? N2 C7 C2 105.35(10) . . ? C6 C7 C2 121.41(11) . . ? C3 C2 O3 127.26(10) . . ? C3 C2 C7 123.83(11) . . ? O3 C2 C7 108.92(10) . . ? C2 C3 C4 113.68(10) . . ? C2 C3 H3 123.2 . . ? C4 C3 H3 123.2 . . ? C5 C4 C3 124.49(11) . . ? C5 C4 N3 118.45(10) . . ? C3 C4 N3 117.05(10) . . ? C6 C5 C4 120.10(11) . . ? C6 C5 H5 120 . . ? C4 C5 H5 120 . . ? C7 C6 C5 116.49(11) . . ? C7 C6 H6 121.8 . . ? C5 C6 H6 121.8 . . ? loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag S1 C1 1.6343(12) . ? O1 N3 1.2242(15) . ? O2 N3 1.2301(14) . ? O3 C1 1.3775(14) . ? O3 C2 1.3811(13) . ? N2 C1 1.3507(15) . ? N2 C7 1.3822(15) . ? N2 H2 0.852(17) . ? N3 C4 1.4609(15) . ? C7 C6 1.3889(16) . ? C7 C2 1.3894(16) . ? C2 C3 1.3717(16) . ? C3 C4 1.3925(16) . ? C3 H3 0.95 . ? C4 C5 1.3911(17) . ? C5 C6 1.3898(17) . ? C5 H5 0.95 . ? C6 H6 0.95 . ? loop_ _geom_hbond_atom_site_label_D _geom_hbond_atom_site_label_H _geom_hbond_atom_site_label_A _geom_hbond_distance_DH _geom_hbond_distance_HA _geom_hbond_distance_DA _geom_hbond_angle_DHA _geom_hbond_site_symmetry_A _geom_hbond_publ_flag N2 H2 O1 0.852(17) 2.454(17) 3.0756(14) 130.4(14) 2_656 yes N2 H2 O2 0.852(17) 2.253(17) 3.0556(14) 157.0(15) 2_656 yes C3 H3 S1 0.95 2.88 3.8230(12) 170.2 3_566 yes C6 H6 O1 0.95 2.63 3.2441(16) 123.1 2_656 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_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag C7 N2 C1 O3 1.62(13) . . . . ? C7 N2 C1 S1 -178.90(10) . . . . ? C2 O3 C1 N2 -1.19(12) . . . . ? C2 O3 C1 S1 179.28(8) . . . . ? C1 N2 C7 C6 178.79(13) . . . . ? C1 N2 C7 C2 -1.39(13) . . . . ? C1 O3 C2 C3 -179.74(12) . . . . ? C1 O3 C2 C7 0.34(12) . . . . ? N2 C7 C2 C3 -179.31(11) . . . . ? C6 C7 C2 C3 0.54(19) . . . . ? N2 C7 C2 O3 0.61(13) . . . . ? C6 C7 C2 O3 -179.53(11) . . . . ? O3 C2 C3 C4 179.09(11) . . . . ? C7 C2 C3 C4 -0.99(17) . . . . ? C2 C3 C4 C5 0.51(17) . . . . ? C2 C3 C4 N3 -178.93(10) . . . . ? O1 N3 C4 C5 172.28(11) . . . . ? O2 N3 C4 C5 -8.66(17) . . . . ? O1 N3 C4 C3 -8.24(16) . . . . ? O2 N3 C4 C3 170.81(11) . . . . ? C3 C4 C5 C6 0.45(19) . . . . ? N3 C4 C5 C6 179.88(11) . . . . ? N2 C7 C6 C5 -179.73(12) . . . . ? C2 C7 C6 C5 0.47(18) . . . . ? C4 C5 C6 C7 -0.92(18) . . . . ?