#------------------------------------------------------------------------------ #$Date: 2025-08-19 07:12:48 +0100 (Tue, 19 Aug 2025) $ #$Revision: 301798 $ #$URL: svn://www.crystallography.net/cod/cif/2/01/22/2012215.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_2012215 loop_ _publ_author_name 'Wolf, Wojciech M.' _publ_section_title ; X-ray investigations of sulfur-containing fungicides. IV. 4'-{[Benzoyl(4-chlorophenylhydrazono)methyl]sulfonyl}acetanilide and 4'-{[benzoyl(4-methoxyphenylhydrazono)methyl]sulfonyl}acetanilide ; _journal_issue 9 _journal_name_full 'Acta Crystallographica Section C' _journal_page_first 1112 _journal_page_last 1115 _journal_paper_doi 10.1107/S0108270101010642 _journal_volume 57 _journal_year 2001 _chemical_formula_moiety 'C23 H21 N3 O5 S' _chemical_formula_sum 'C23 H21 N3 O5 S' _chemical_formula_weight 451.49 _chemical_name_systematic ; 4'-{[benzoyl(4-methoxyphenylhydrazono)methyl]sulfonyl}acetanilide ; _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 'manual editing of the SHELXL97 .cif file' _cell_angle_alpha 90 _cell_angle_beta 91.53(3) _cell_angle_gamma 90 _cell_formula_units_Z 4 _cell_length_a 11.4897(12) _cell_length_b 7.4158(9) _cell_length_c 25.507(3) _cell_measurement_reflns_used 48 _cell_measurement_temperature 293(2) _cell_measurement_theta_max 10.2 _cell_measurement_theta_min 4.5 _cell_volume 2172.6(4) _computing_cell_refinement P3 _computing_data_collection 'P3 (Siemens, 1989)' _computing_data_reduction 'XDISK (Siemens, 1991)' _computing_molecular_graphics 'InsightII (Molecular Simulations, 1997) and XP (Siemens, 1990)' _computing_publication_material SHELXL97 _computing_structure_refinement SHELXL97 _computing_structure_solution 'SHELXS97 (Sheldrick, 1997)' _diffrn_ambient_temperature 293(2) _diffrn_measured_fraction_theta_full .920 _diffrn_measured_fraction_theta_max .920 _diffrn_measurement_device_type 'Siemens P3' _diffrn_measurement_method \w/2\q _diffrn_radiation_monochromator graphite _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_type MoK\a _diffrn_radiation_wavelength .71073 _diffrn_reflns_av_R_equivalents .052 _diffrn_reflns_av_sigmaI/netI .040 _diffrn_reflns_limit_h_max 13 _diffrn_reflns_limit_h_min -1 _diffrn_reflns_limit_k_max 8 _diffrn_reflns_limit_k_min -1 _diffrn_reflns_limit_l_max 30 _diffrn_reflns_limit_l_min -30 _diffrn_reflns_number 5473 _diffrn_reflns_theta_full 25.00 _diffrn_reflns_theta_max 25 _diffrn_reflns_theta_min 1.93 _diffrn_standards_decay_% 18 _diffrn_standards_interval_count 97 _diffrn_standards_number 3 _exptl_absorpt_coefficient_mu .190 _exptl_absorpt_correction_type none _exptl_crystal_colour yellow _exptl_crystal_density_diffrn 1.380 _exptl_crystal_density_method 'not measured' _exptl_crystal_description plate _exptl_crystal_F_000 944 _exptl_crystal_size_max .55 _exptl_crystal_size_mid .35 _exptl_crystal_size_min .15 _refine_diff_density_max .22 _refine_diff_density_min -.34 _refine_ls_extinction_method none _refine_ls_goodness_of_fit_ref 1.033 _refine_ls_hydrogen_treatment mixed _refine_ls_matrix_type full _refine_ls_number_parameters 317 _refine_ls_number_reflns 3823 _refine_ls_number_restraints 0 _refine_ls_restrained_S_all 1.033 _refine_ls_R_factor_all .070 _refine_ls_R_factor_gt .042 _refine_ls_shift/su_max .002 _refine_ls_shift/su_mean .000 _refine_ls_structure_factor_coef Fsqd _refine_ls_weighting_details 'w = 1/[\s^2^(Fo^2^)+(0.0674P)^2^+0.2858P] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_ref .127 _reflns_number_gt 2647 _reflns_number_total 3823 _reflns_threshold_expression I>2\s(I) _cod_data_source_file jz1471.cif _cod_data_source_block II _cod_original_cell_volume 2172.5(4) _cod_original_sg_symbol_H-M 'P 21/n' _cod_database_code 2012215 _cod_database_fobs_code 2012215 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 S .61621(5) .59505(10) .17476(2) .0521(2) Uani d . 1 . . S O1 .60399(17) .7844(3) .16310(7) .0666(6) Uani d . 1 . . O O2 .70669(15) .5408(3) .21149(7) .0706(6) Uani d . 1 . . O O3 .38431(15) .5667(3) .12279(6) .0559(5) Uani d . 1 . . O O4 .6503(2) -.0913(3) -.00458(8) .0757(6) Uani d . 1 . . O O5 .46487(18) .2345(3) .48744(7) .0756(6) Uani d . 1 . . O N1 .47501(15) .4549(3) .25010(7) .0398(5) Uani d . 1 . . N N2 .55876(17) .4410(3) .28465(7) .0453(5) Uani d . 1 . . N H2 .630(3) .465(4) .2764(11) .070(9) Uiso d . 1 . . H N3 .63852(18) .2040(3) -.02660(8) .0483(5) Uani d . 1 . . N H3 .628(2) .276(4) -.0542(11) .053(7) Uiso d . 1 . . H C1 .48435(19) .5148(3) .20211(9) .0429(6) Uani d . 1 . . C C2 .37866(19) .5247(3) .16923(8) .0411(5) Uani d . 1 . . C C3 .26206(19) .4801(3) .19102(8) .0392(5) Uani d . 1 . . C C4 .2266(2) .5384(3) .23990(9) .0440(6) Uani d . 1 . . C H4 .2798(15) .5993(18) .2628(7) .057(3) Uiso calc R 1 . . H C5 .1139(2) .5073(4) .25510(10) .0524(7) Uani d . 1 . . C H5 .0898(7) .5480(13) .2885(10) .057(3) Uiso calc R 1 . . H C6 .0364(2) .4183(4) .22238(11) .0578(7) Uani d . 1 . . C H6 -.040(2) .3982(7) .2329(3) .057(3) Uiso calc R 1 . . H C7 .0705(2) .3588(4) .17432(11) .0555(7) Uani d . 1 . . C H7 .0185(15) .2965(19) .1526(6) .057(3) Uiso calc R 1 . . H C8 .1824(2) .3916(3) .15829(9) .0473(6) Uani d . 1 . . C H8 .2044(7) .3543(12) .1255(10) .057(3) Uiso calc R 1 . . H C9 .6335(2) .4780(4) .11585(9) .0472(6) Uani d . 1 . . C C10 .6465(2) .2921(4) .11625(11) .0591(7) Uani d . 1 . . C H10 .6528(3) .229(2) .1488(10) .063(4) Uiso calc R 1 . . H C11 .6503(2) .1982(4) .06995(10) .0584(7) Uani d . 1 . . C H11 .6575(3) .079(4) .07039(10) .063(4) Uiso calc R 1 . . H C12 .64300(19) .2895(3) .02237(9) .0441(6) Uani d . 1 . . C C13 .6359(2) .4766(3) .02270(10) .0468(6) Uani d . 1 . . C H13 .6355(2) .538(2) -.0084(10) .063(4) Uiso calc R 1 . . H C14 .6293(2) .5702(4) .06881(10) .0493(6) Uani d . 1 . . C H14 .6218(3) .698(4) .06842(10) .063(4) Uiso calc R 1 . . H C15 .6394(2) .0249(4) -.03769(11) .0525(6) Uani d . 1 . . C C16 .6277(3) -.0188(4) -.09492(11) .0659(8) Uani d . 1 . . C H161 .5726(11) .0659(16) -.1120(4) .119(8) Uiso calc R 1 . . H H162 .5986(6) -.143(2) -.09927(15) .119(8) Uiso calc R 1 . . H H163 .7044(15) -.0080(5) -.1111(3) .119(8) Uiso calc R 1 . . H C17 .53525(18) .3858(3) .33639(8) .0391(5) Uani d . 1 . . C C18 .4251(2) .3332(3) .35020(9) .0458(6) Uani d . 1 . . C H18 .3646(17) .3325(4) .3256(7) .057(4) Uiso calc R 1 . . H C19 .4068(2) .2820(4) .40092(9) .0487(6) Uani d . 1 . . C H19 .334(2) .2445(11) .4101(3) .057(4) Uiso calc R 1 . . H C20 .4951(2) .2857(4) .43840(9) .0499(6) Uani d . 1 . . C C21 .6048(2) .3385(4) .42436(10) .0608(7) Uani d . 1 . . C H21 .6663(17) .3415(4) .4496(7) .057(4) Uiso calc R 1 . . H C22 .6241(2) .3872(4) .37291(10) .0545(7) Uani d . 1 . . C H22 .697(2) .4206(11) .3634(3) .057(4) Uiso calc R 1 . . H C23 .5531(3) .2246(6) .52671(12) .0906(12) Uani d . 1 . . C H231 .6058(12) .126(2) .5189(2) .118(8) Uiso calc R 1 . . H H232 .5183(7) .2033(7) .5605(7) .118(8) Uiso calc R 1 . . H H233 .5962(10) .337(2) .52788(12) .118(8) Uiso calc R 1 . . H 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 S .0471(3) .0709(5) .0389(3) -.0078(3) .0141(2) -.0010(3) O1 .0778(13) .0587(12) .0647(13) -.0157(10) .0300(10) -.0059(10) O2 .0440(9) .1245(18) .0437(10) -.0098(11) .0093(8) .0027(11) O3 .0560(10) .0772(13) .0349(9) .0039(9) .0088(7) .0157(9) O4 .1111(17) .0494(12) .0662(14) .0074(11) -.0021(12) .0135(10) O5 .0836(13) .1034(17) .0399(11) -.0027(12) .0059(9) .0156(11) N1 .0426(10) .0446(11) .0324(10) .0025(9) .0058(8) -.0005(8) N2 .0359(10) .0646(14) .0356(11) -.0010(10) .0056(8) .0014(10) N3 .0604(13) .0472(13) .0380(12) .0092(10) .0134(9) .0086(10) C1 .0424(12) .0493(14) .0377(13) -.0014(11) .0098(9) .0022(11) C2 .0468(13) .0447(13) .0322(13) .0059(11) .0091(9) .0035(10) C3 .0431(12) .0424(13) .0324(11) .0041(10) .0035(9) .0067(10) C4 .0477(13) .0496(14) .0349(13) .0037(11) .0052(10) .0010(11) C5 .0552(15) .0646(17) .0380(13) .0071(13) .0139(11) .0041(12) C6 .0460(13) .0717(19) .0562(16) -.0042(13) .0101(12) .0156(14) C7 .0536(14) .0634(18) .0494(15) -.0138(13) -.0032(12) .0047(13) C8 .0545(14) .0529(15) .0345(12) .0012(12) -.0009(10) .0016(11) C9 .0439(13) .0628(17) .0353(13) .0029(12) .0112(10) .0051(12) C10 .0743(18) .0642(19) .0392(15) .0167(15) .0115(12) .0152(13) C11 .0817(19) .0529(16) .0414(15) .0229(14) .0138(12) .0103(12) C12 .0414(12) .0525(15) .0390(13) .0089(11) .0125(9) .0086(11) C13 .0532(14) .0519(15) .0358(13) .0028(12) .0136(10) .0132(11) C14 .0542(14) .0511(15) .0433(14) .0021(12) .0140(11) .0082(12) C15 .0511(14) .0547(17) .0521(16) .0044(12) .0092(11) .0066(13) C16 .0777(19) .0611(18) .0594(18) -.0011(15) .0101(14) -.0057(14) C17 .0394(11) .0439(13) .0342(11) .0024(10) .0032(9) -.0018(10) C18 .0420(12) .0596(16) .0357(12) -.0046(11) .0005(10) -.0009(11) C19 .0449(13) .0588(16) .0429(14) -.0067(12) .0079(10) .0019(12) C20 .0592(14) .0567(16) .0340(12) .0042(13) .0038(10) .0049(12) C21 .0508(14) .087(2) .0437(15) .0048(14) -.0103(11) .0039(15) C22 .0357(12) .082(2) .0463(14) .0014(13) .0021(10) .0043(14) C23 .114(3) .116(3) .0415(16) .003(2) -.0097(17) .0160(18) loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C .0033 .0016 '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' N N .0061 .0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O .0106 .0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' S S .1246 .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 _geom_angle_publ_flag O1 S O2 118.15(13) y O1 S C1 109.04(11) y O1 S C9 108.56(12) y O2 S C1 104.97(11) y O2 S C9 108.87(12) y C1 S C9 106.67(12) y N2 N1 C1 125.93(19) y N1 N2 C17 120.15(18) y N1 C1 C2 117.82(19) y S C1 N1 124.71(17) y S C1 C2 117.40(16) y O3 C2 C1 120.2(2) y O3 C2 C3 118.9(2) y C1 C2 C3 120.89(19) y C15 N3 C12 128.9(2) y C20 O5 C23 118.1(2) y C8 C3 C4 118.9(2) n C8 C3 C2 117.5(2) n C4 C3 C2 123.3(2) n C5 C4 C3 119.9(2) n C6 C5 C4 120.5(2) n C7 C6 C5 120.2(2) n C7 C8 C3 120.6(2) n C6 C7 C8 119.9(3) n C14 C9 C10 120.0(3) n C14 C9 S 119.9(2) n C10 C9 S 120.1(2) n C11 C10 C9 120.3(3) n C10 C11 C12 120.1(3) n C13 C12 C11 118.9(2) n C13 C12 N3 117.2(2) n C11 C12 N3 123.9(2) n C14 C13 C12 121.1(2) n C13 C14 C9 119.6(2) n O4 C15 N3 123.5(3) n O4 C15 C16 122.0(3) n N3 C15 C16 114.5(2) n C22 C17 C18 120.2(2) n C22 C17 N2 118.5(2) n C18 C17 N2 121.3(2) n C19 C18 C17 119.0(2) n C18 C19 C20 121.4(2) n O5 C20 C19 115.5(2) n O5 C20 C21 125.2(2) n C19 C20 C21 119.2(2) n C20 C21 C22 119.5(2) n C17 C22 C21 120.7(2) n N1 N2 H2 120.4(19) n C17 N2 H2 119.5(19) n C15 N3 H3 115.3(17) n C12 N3 H3 115.6(17) n C5 C4 H4 120.0 n C3 C4 H4 120.0 n C6 C5 H5 119.8 n C4 C5 H5 119.8 n C7 C6 H6 119.9 n C5 C6 H6 119.9 n C6 C7 H7 120.0 n C8 C7 H7 120.0 n C7 C8 H8 119.7 n C3 C8 H8 119.7 n C11 C10 H10 119.9 n C9 C10 H10 119.9 n C10 C11 H11 120.0 n C12 C11 H11 120.0 n C14 C13 H13 119.5 n C12 C13 H13 119.5 n C13 C14 H14 120.2 n C9 C14 H14 120.2 n C15 C16 H161 109.5 n C15 C16 H162 109.5 n H161 C16 H162 109.5 n C15 C16 H163 109.5 n H161 C16 H163 109.5 n H162 C16 H163 109.5 n C19 C18 H18 120.5 n C17 C18 H18 120.5 n C18 C19 H19 119.3 n C20 C19 H19 119.3 n C20 C21 H21 120.3 n C22 C21 H21 120.3 n C17 C22 H22 119.7 n C21 C22 H22 119.7 n O5 C23 H231 109.5 n O5 C23 H232 109.5 n H231 C23 H232 109.5 n O5 C23 H233 109.5 n H231 C23 H233 109.5 n H232 C23 H233 109.5 n 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 S O1 . 1.441(2) y S O2 . 1.438(2) y S C1 . 1.787(2) y S C9 . 1.751(3) y O3 C2 . 1.228(3) y N1 N2 . 1.291(3) y N1 C1 . 1.309(3) y N2 C17 . 1.415(3) y C1 C2 . 1.459(3) y C2 C3 . 1.501(3) y C3 C8 . 1.387(3) n C3 C4 . 1.391(3) n C4 C5 . 1.381(3) n C5 C6 . 1.373(4) n C6 C7 . 1.370(4) n C7 C8 . 1.382(4) n C9 C10 . 1.386(4) n C9 C14 . 1.381(3) n C10 C11 . 1.373(4) n C11 C12 . 1.390(3) n C12 C13 . 1.390(3) n C13 C14 . 1.370(3) n C17 C22 . 1.363(3) n C17 C18 . 1.378(3) n C18 C19 . 1.370(3) n C19 C20 . 1.376(3) n C20 C21 . 1.376(4) n C21 C22 . 1.385(4) n N3 C12 . 1.401(3) y N3 C15 . 1.358(3) y O4 C15 . 1.211(3) y C15 C16 . 1.498(4) n O5 C20 . 1.361(3) y O5 C23 . 1.408(4) y N2 H2 . .86(3) n N3 H3 . .89(3) n C4 H4 . .95 n C5 H5 . .95 n C6 H6 . .94 n C7 H7 . .93 n C8 H8 . .92 n C10 H10 . .95 n C11 H11 . .89 n C13 H13 . .92 n C14 H14 . .95 n C16 H161 . .99 n C16 H162 . .99 n C16 H163 . .99 n C18 H18 . .92 n C19 H19 . .92 n C21 H21 . .94 n C22 H22 . .91 n C23 H231 . .97 n C23 H232 . .97 n C23 H233 . .97 n loop_ _geom_contact_atom_site_label_1 _geom_contact_atom_site_label_2 _geom_contact_distance _geom_contact_publ_flag S O3 2.952(2) y S N2 3.114(2) y O1 C2 3.234(3) y O2 C2 3.894(3) y O1 N2 4.056(3) n O2 N2 2.663(3) n N2 C2 3.607(3) n 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 N2 H2 O2 . .86(3) 1.98(3) 2.663(3) 135(2) N3 H3 O3 3_665 .89(3) 2.10(3) 2.991(3) 174(2) C11 H11 O4 . .89 2.29 2.867(4) 122 C21 H21 O4 2_655 .94 2.55 3.474(4) 167 C14 H14 O4 1_565 .95 2.46 3.144(3) 129 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 S C1 C2 O3 8.4(3) y S C1 N1 N2 -1.4(4) y O1 S C1 C2 62.1(2) y O1 S C1 N1 -114.9(2) y O2 S C1 C2 -170.4(2) y O2 S C1 N1 12.6(3) y S C1 C2 C3 -173.0(2) n N1 C1 C2 O3 -174.4(2) n N1 C1 C2 C3 4.2(3) n N2 N1 C1 C2 -178.4(2) n C1 N1 N2 C17 175.6(2) n C9 S C1 N1 128.0(2) n C9 S C1 C2 -55.0(2) n C12 N3 C15 O4 -3.9(4) n C12 N3 C15 C16 177.2(2) n C23 O5 C20 C21 -3.7(4) n C23 O5 C20 C19 176.1(3) n loop_ _cod_related_entry_id _cod_related_entry_database _cod_related_entry_code 1 ChemSpider 21182043 2 PubChem 15113112