#------------------------------------------------------------------------------ #$Date: 2025-08-19 11:43:10 +0100 (Tue, 19 Aug 2025) $ #$Revision: 301803 $ #$URL: svn://www.crystallography.net/cod/cif/2/20/26/2202616.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_2202616 loop_ _publ_author_name 'Dupont, L\'eon' 'Somers, Fabian' 'De Tullio, Pascal' 'Pirotte, Bernard' _publ_section_title ; 3-Isopropylamino-7-nitro-1,4,2-benzodithiazine 1,1-dioxide ; _journal_issue 10 _journal_name_full 'Acta Crystallographica Section E' _journal_page_first o1509 _journal_page_last o1511 _journal_paper_doi 10.1107/S1600536803020324 _journal_volume 59 _journal_year 2003 _chemical_formula_iupac 'C10 H11 N3 O4 S2' _chemical_formula_moiety 'C10 H11 N3 O4 S2' _chemical_formula_sum 'C10 H11 N3 O4 S2' _chemical_formula_weight 301.34 _chemical_name_systematic ; 3-isopropylamino-7-nitro-1,4,2-benzothiadiazine 1,1-dioxide ; _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' _atom_sites_solution_hydrogens geom _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _audit_creation_method SHELXL-97 _cell_angle_alpha 90.00 _cell_angle_beta 101.840(12) _cell_angle_gamma 90.00 _cell_formula_units_Z 4 _cell_length_a 7.4143(7) _cell_length_b 21.461(4) _cell_length_c 8.3958(11) _cell_measurement_reflns_used 31 _cell_measurement_temperature 293(2) _cell_measurement_theta_max 41.5 _cell_measurement_theta_min 34.1 _cell_volume 1307.5(3) _computing_cell_refinement DIF4 _computing_data_collection 'DIF4 (Stoe & Cie, 1987)' _computing_data_reduction 'REDU4 (Stoe & Cie, 1987)' _computing_molecular_graphics 'ORTEPIII (Burnett & Johnson, 1996)' _computing_publication_material SHELXL97 _computing_structure_refinement 'SHELXL97 (Sheldrick, 1997)' _computing_structure_solution 'SHELXS97 (Sheldrick, 1997)' _diffrn_ambient_temperature 293(2) _diffrn_measured_fraction_theta_full 0.979 _diffrn_measured_fraction_theta_max 0.979 _diffrn_measurement_device_type 'Stoe--Siemens AED four-circle' _diffrn_measurement_method \w _diffrn_radiation_monochromator graphite _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_type CuK\a _diffrn_radiation_wavelength 1.54180 _diffrn_reflns_av_R_equivalents 0.0444 _diffrn_reflns_av_sigmaI/netI 0.0275 _diffrn_reflns_limit_h_max 0 _diffrn_reflns_limit_h_min -8 _diffrn_reflns_limit_k_max 25 _diffrn_reflns_limit_k_min 0 _diffrn_reflns_limit_l_max 10 _diffrn_reflns_limit_l_min -9 _diffrn_reflns_number 2498 _diffrn_reflns_theta_full 67.85 _diffrn_reflns_theta_max 67.85 _diffrn_reflns_theta_min 4.12 _diffrn_standards_decay_% 10 _diffrn_standards_interval_time 60 _diffrn_standards_number 2 _exptl_absorpt_coefficient_mu 3.849 _exptl_absorpt_correction_T_max 0.270 _exptl_absorpt_correction_T_min 0.137 _exptl_absorpt_correction_type '\y scan' _exptl_absorpt_process_details '(EMPIR; Stoe & Cie, 1987)' _exptl_crystal_colour colourless _exptl_crystal_density_diffrn 1.531 _exptl_crystal_density_method 'not measured' _exptl_crystal_description prism _exptl_crystal_F_000 624 _exptl_crystal_size_max 0.68 _exptl_crystal_size_mid 0.53 _exptl_crystal_size_min 0.34 _refine_diff_density_max 0.437 _refine_diff_density_min -0.566 _refine_ls_extinction_coef 0.0102(13) _refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^ _refine_ls_extinction_method SHELXL97 _refine_ls_goodness_of_fit_ref 1.081 _refine_ls_hydrogen_treatment mixed _refine_ls_matrix_type full _refine_ls_number_parameters 178 _refine_ls_number_reflns 2317 _refine_ls_number_restraints 0 _refine_ls_restrained_S_all 1.081 _refine_ls_R_factor_all 0.0593 _refine_ls_R_factor_gt 0.0524 _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^)+(0.1169P)^2^+0.1969P] where P = (Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_gt 0.1519 _refine_ls_wR_factor_ref 0.1563 _reflns_number_gt 1955 _reflns_number_total 2317 _reflns_threshold_expression I>2\s(I) _cod_data_source_file dn6092.cif _cod_data_source_block II _cod_original_sg_symbol_H-M 'P 21/n' _cod_database_code 2202616 _cod_database_fobs_code 2202616 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_disorder_assembly _atom_site_disorder_group _atom_site_type_symbol S1 0.22976(9) 0.09769(3) 0.11063(8) 0.0417(3) Uani d . 1 . . S N2 0.3981(3) 0.14534(10) 0.1511(3) 0.0459(6) Uani d . 1 . . N C3 0.5667(4) 0.12775(13) 0.1460(3) 0.0430(6) Uani d . 1 . . C S4 0.65181(9) 0.05028(3) 0.15770(9) 0.0479(3) Uani d . 1 . . S C5 0.4841(4) 0.00923(13) 0.2358(3) 0.0425(6) Uani d . 1 . . C C6 0.5389(4) -0.04736(14) 0.3117(4) 0.0505(7) Uani d . 1 . . C H6 0.6600 -0.0607 0.3214 0.061 Uiso calc R 1 . . H C7 0.4167(4) -0.08335(15) 0.3718(4) 0.0537(7) Uani d . 1 . . C H7 0.4523 -0.1217 0.4194 0.064 Uiso calc R 1 . . H C8 0.2376(4) -0.06151(14) 0.3606(3) 0.0452(6) Uani d . 1 . . C C9 0.1786(4) -0.00546(13) 0.2874(3) 0.0437(6) Uani d . 1 . . C H9 0.0589 0.0086 0.2823 0.052 Uiso calc R 1 . . H C10 0.3026(3) 0.02921(12) 0.2217(3) 0.0406(6) Uani d . 1 . . C N11 0.6957(3) 0.16836(11) 0.1314(3) 0.0486(6) Uani d . 1 . . N H11 0.798(5) 0.1592(19) 0.143(4) 0.058 Uiso d . 1 . . H C12 0.6659(4) 0.23559(13) 0.1002(4) 0.0508(7) Uani d . 1 . . C H12 0.5338 0.2427 0.0601 0.061 Uiso calc R 1 . . H C13 0.7255(8) 0.27127(18) 0.2564(6) 0.0918(15) Uani d . 1 . . C H13A 0.6584 0.2566 0.3354 0.138 Uiso calc R 1 . . H H13B 0.7012 0.3148 0.2366 0.138 Uiso calc R 1 . . H H13C 0.8551 0.2652 0.2970 0.138 Uiso calc R 1 . . H C14 0.7657(7) 0.2553(2) -0.0292(6) 0.0967(15) Uani d . 1 . . C H14A 0.8961 0.2515 0.0110 0.145 Uiso calc R 1 . . H H14B 0.7358 0.2978 -0.0586 0.145 Uiso calc R 1 . . H H14C 0.7291 0.2291 -0.1231 0.145 Uiso calc R 1 . . H N3 0.1082(4) -0.09914(13) 0.4297(3) 0.0554(7) Uani d . 1 . . N O1 0.1917(3) 0.08075(10) -0.0577(2) 0.0548(5) Uani d . 1 . . O O2 0.0799(3) 0.12379(10) 0.1739(3) 0.0563(6) Uani d . 1 . . O O3 -0.0370(3) -0.07592(12) 0.4450(3) 0.0640(6) Uani d . 1 . . O O4 0.1545(4) -0.15259(13) 0.4707(4) 0.0868(9) Uani d . 1 . . O 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 0.0373(4) 0.0340(4) 0.0531(4) 0.0036(2) 0.0077(3) 0.0022(3) N2 0.0402(12) 0.0332(11) 0.0647(14) 0.0035(9) 0.0115(10) -0.0021(10) C3 0.0454(15) 0.0340(13) 0.0485(13) -0.0013(11) 0.0068(11) -0.0049(11) S4 0.0415(4) 0.0346(4) 0.0701(5) 0.0036(3) 0.0174(3) -0.0013(3) C5 0.0397(13) 0.0374(14) 0.0505(14) 0.0030(11) 0.0094(11) -0.0033(11) C6 0.0436(15) 0.0404(15) 0.0666(17) 0.0079(12) 0.0093(13) 0.0042(13) C7 0.0522(17) 0.0412(14) 0.0653(18) 0.0041(13) 0.0064(14) 0.0058(13) C8 0.0445(14) 0.0420(14) 0.0486(14) -0.0026(12) 0.0084(11) 0.0026(12) C9 0.0413(14) 0.0382(14) 0.0508(14) 0.0000(11) 0.0078(11) -0.0019(11) C10 0.0409(13) 0.0334(13) 0.0464(13) 0.0035(11) 0.0066(10) -0.0011(10) N11 0.0398(12) 0.0347(12) 0.0714(15) -0.0005(10) 0.0115(11) 0.0021(11) C12 0.0454(15) 0.0351(14) 0.0688(18) -0.0012(12) 0.0044(13) 0.0076(13) C13 0.123(4) 0.046(2) 0.092(3) 0.001(2) -0.012(3) -0.0123(19) C14 0.104(3) 0.078(3) 0.116(4) 0.010(3) 0.042(3) 0.040(3) N3 0.0539(15) 0.0526(15) 0.0577(14) -0.0073(12) 0.0066(11) 0.0100(11) O1 0.0609(13) 0.0482(12) 0.0518(11) 0.0017(10) 0.0034(9) 0.0029(9) O2 0.0415(11) 0.0459(12) 0.0845(14) 0.0101(9) 0.0199(10) 0.0066(11) O3 0.0532(13) 0.0689(16) 0.0716(14) -0.0041(11) 0.0166(11) 0.0075(12) O4 0.0747(17) 0.0568(15) 0.131(2) 0.0000(13) 0.0253(16) 0.0353(16) loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0181 0.0091 '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 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' S S 0.3331 0.5567 '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 O1 S1 O2 116.91(14) no O1 S1 N2 111.14(13) no O2 S1 N2 107.54(13) no O1 S1 C10 106.71(12) no O2 S1 C10 107.74(13) no N2 S1 C10 106.26(12) yes C3 N2 S1 121.10(19) yes N2 C3 N11 121.7(3) yes N2 C3 S4 126.7(2) yes N11 C3 S4 111.6(2) yes C5 S4 C3 102.69(13) yes C6 C5 C10 119.5(3) no C6 C5 S4 116.5(2) no C10 C5 S4 124.0(2) no C7 C6 C5 120.6(3) no C7 C6 H6 119.7 no C5 C6 H6 119.7 no C6 C7 C8 118.8(3) no C6 C7 H7 120.6 no C8 C7 H7 120.6 no C9 C8 C7 122.2(3) no C9 C8 N3 119.0(3) no C7 C8 N3 118.8(3) no C8 C9 C10 118.1(3) no C8 C9 H9 120.9 no C10 C9 H9 120.9 no C9 C10 C5 120.7(2) no C9 C10 S1 120.2(2) no C5 C10 S1 119.1(2) no C3 N11 C12 125.3(3) yes C3 N11 H11 122(3) no C12 N11 H11 112(3) no N11 C12 C14 109.1(3) no N11 C12 C13 109.7(3) no C14 C12 C13 112.9(4) no N11 C12 H12 108.4 no C14 C12 H12 108.4 no C13 C12 H12 108.4 no C12 C13 H13A 109.5 no C12 C13 H13B 109.5 no H13A C13 H13B 109.5 no C12 C13 H13C 109.5 no H13A C13 H13C 109.5 no H13B C13 H13C 109.5 no C12 C14 H14A 109.5 no C12 C14 H14B 109.5 no H14A C14 H14B 109.5 no C12 C14 H14C 109.5 no H14A C14 H14C 109.5 no H14B C14 H14C 109.5 no O3 N3 O4 123.8(3) no O3 N3 C8 118.8(3) no O4 N3 C8 117.3(3) no 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 S1 O1 . 1.430(2) no S1 O2 . 1.440(2) no S1 N2 . 1.595(2) yes S1 C10 . 1.765(3) yes N2 C3 . 1.315(3) yes C3 N11 . 1.318(4) yes C3 S4 . 1.774(3) yes S4 C5 . 1.757(3) yes C5 C6 . 1.393(4) no C5 C10 . 1.394(3) no C6 C7 . 1.364(4) no C6 H6 . 0.9300 no C7 C8 . 1.393(4) no C7 H7 . 0.9300 no C8 C9 . 1.381(4) no C8 N3 . 1.462(4) yes C9 C10 . 1.382(4) no C9 H9 . 0.9300 no N11 C12 . 1.475(4) yes N11 H11 . 0.77(4) yes C12 C14 . 1.496(5) no C12 C13 . 1.505(5) no C12 H12 . 0.9800 no C13 H13A . 0.9600 no C13 H13B . 0.9600 no C13 H13C . 0.9600 no C14 H14A . 0.9600 no C14 H14B . 0.9600 no C14 H14C . 0.9600 no N3 O3 . 1.217(4) yes N3 O4 . 1.226(4) yes 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 N11 H11 O2 1_655 0.77(4) 2.19(4) 2.957(3) 175(4) 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 O1 S1 N2 C3 -68.3(3) no O2 S1 N2 C3 162.6(2) no C10 S1 N2 C3 47.4(3) yes S1 N2 C3 N11 159.7(2) yes S1 N2 C3 S4 -20.5(4) yes N2 C3 S4 C5 -16.7(3) yes N11 C3 S4 C5 163.1(2) yes C3 S4 C5 C6 -158.4(2) no C3 S4 C5 C10 23.5(3) no C10 C5 C6 C7 0.1(4) no S4 C5 C6 C7 -178.1(2) no C5 C6 C7 C8 -2.0(5) no C6 C7 C8 C9 1.6(5) no C6 C7 C8 N3 -178.1(3) no C7 C8 C9 C10 0.8(4) no N3 C8 C9 C10 -179.5(2) no C8 C9 C10 C5 -2.8(4) no C8 C9 C10 S1 174.3(2) no C6 C5 C10 C9 2.3(4) no S4 C5 C10 C9 -179.6(2) no C6 C5 C10 S1 -174.8(2) no S4 C5 C10 S1 3.3(3) no O1 S1 C10 C9 -96.9(2) no O2 S1 C10 C9 29.4(3) no N2 S1 C10 C9 144.4(2) no O1 S1 C10 C5 80.2(2) no O2 S1 C10 C5 -153.5(2) no N2 S1 C10 C5 -38.5(2) no N2 C3 N11 C12 -7.5(5) yes S4 C3 N11 C12 172.7(2) no C3 N11 C12 C14 -134.7(4) yes C3 N11 C12 C13 101.2(4) yes C9 C8 N3 O3 -12.0(4) no C7 C8 N3 O3 167.7(3) no C9 C8 N3 O4 168.9(3) no C7 C8 N3 O4 -11.5(4) no loop_ _cod_related_entry_id _cod_related_entry_database _cod_related_entry_code 1 ChemSpider 21131429 2 PubChem 136242863