#------------------------------------------------------------------------------ #$Date: 2016-02-20 05:06:23 +0200 (Sat, 20 Feb 2016) $ #$Revision: 176774 $ #$URL: file:///home/coder/svn-repositories/cod/cif/2/20/40/2204098.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_2204098 loop_ _publ_author_name 'Yu, Zhifang' 'Gu, Xiuyan' 'Zhao, Bing' 'Li, Yan' _publ_section_title ; 3-(4-Methoxyphenyl)-1-phenyl-3-(p-toluenesulfonylamino)propan-1-one ; _journal_issue 8 _journal_name_full 'Acta Crystallographica Section E' _journal_page_first o1290 _journal_page_last o1291 _journal_paper_doi 10.1107/S1600536804015661 _journal_volume 60 _journal_year 2004 _chemical_formula_iupac 'C23 H23 N O4 S' _chemical_formula_moiety 'C23 H23 N O4 S' _chemical_formula_sum 'C23 H23 N O4 S' _chemical_formula_weight 409.49 _chemical_melting_point 399 _chemical_name_systematic ; 3-(4-methoxyphenyl)-1-phenyl-3-(p-toluenesulfonylamino)propan-1-one ; _space_group_IT_number 2 _symmetry_cell_setting triclinic _symmetry_space_group_name_Hall '-P 1' _symmetry_space_group_name_H-M 'P -1' _atom_sites_solution_hydrogens geom _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _cell_angle_alpha 94.267(5) _cell_angle_beta 91.985(4) _cell_angle_gamma 116.676(4) _cell_formula_units_Z 2 _cell_length_a 9.884(3) _cell_length_b 9.924(3) _cell_length_c 11.738(3) _cell_measurement_reflns_used 991 _cell_measurement_temperature 293(2) _cell_measurement_theta_max 26.39 _cell_measurement_theta_min 3.00 _cell_volume 1023.0(5) _computing_cell_refinement SMART _computing_data_collection 'SMART (Bruker, 1997)' _computing_data_reduction 'SAINT (Bruker, 1997)' _computing_molecular_graphics 'SHELXTL (Bruker, 1997)' _computing_publication_material SHELXTL _computing_structure_refinement 'SHELXL97 (Sheldrick, 1997)' _computing_structure_solution 'SHELXS97 (Sheldrick, 1997)' _diffrn_ambient_temperature 293(2) _diffrn_measured_fraction_theta_full 0.996 _diffrn_measured_fraction_theta_max 0.996 _diffrn_measurement_device_type 'Bruker SMART 1000 CCD area-detector' _diffrn_measurement_method '\y and \w' _diffrn_radiation_monochromator graphite _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_type 'Mo K\a' _diffrn_radiation_wavelength 0.71073 _diffrn_reflns_av_R_equivalents 0.0183 _diffrn_reflns_av_sigmaI/netI 0.0411 _diffrn_reflns_limit_h_max 11 _diffrn_reflns_limit_h_min -11 _diffrn_reflns_limit_k_max 8 _diffrn_reflns_limit_k_min -11 _diffrn_reflns_limit_l_max 13 _diffrn_reflns_limit_l_min -13 _diffrn_reflns_number 5353 _diffrn_reflns_theta_full 25.01 _diffrn_reflns_theta_max 25.01 _diffrn_reflns_theta_min 2.31 _diffrn_standards_number 0 _exptl_absorpt_coefficient_mu 0.188 _exptl_absorpt_correction_T_max 0.978 _exptl_absorpt_correction_T_min 0.965 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details '(SADABS; Sheldrick, 1996)' _exptl_crystal_colour colorless _exptl_crystal_density_diffrn 1.329 _exptl_crystal_density_method 'not measured' _exptl_crystal_description prism _exptl_crystal_F_000 432 _exptl_crystal_size_max 0.26 _exptl_crystal_size_mid 0.16 _exptl_crystal_size_min 0.12 _refine_diff_density_max 0.299 _refine_diff_density_min -0.359 _refine_ls_extinction_method none _refine_ls_goodness_of_fit_ref 1.042 _refine_ls_hydrogen_treatment constr _refine_ls_matrix_type full _refine_ls_number_parameters 264 _refine_ls_number_reflns 3607 _refine_ls_number_restraints 0 _refine_ls_restrained_S_all 1.042 _refine_ls_R_factor_all 0.0805 _refine_ls_R_factor_gt 0.0500 _refine_ls_shift/su_max 0.002 _refine_ls_shift/su_mean 0.000 _refine_ls_structure_factor_coef Fsqd _refine_ls_weighting_details 'w = 1/[\s^2^(Fo^2^)+(0.0503P)^2^+0.4833P] where P = (Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_gt 0.1110 _refine_ls_wR_factor_ref 0.1271 _reflns_number_gt 2537 _reflns_number_total 3607 _reflns_threshold_expression I>2\s(I) _cod_data_source_file wn6259.cif _cod_data_source_block I _cod_depositor_comments ; The following automatic conversions were performed: '_symmetry_cell_setting' value 'Triclinic' changed to 'triclinic' according to '/home/saulius/struct/CIF-dictionaries/cif_core.dic' dictionary named 'cif_core.dic' version 2.4.1 from 2010-06-29. Automatic conversion script Id: cif_fix_enum 1527 2010-12-29 10:47:43Z saulius The following automatic conversions were performed: '_symmetry_cell_setting' value 'Triclinic' changed to 'triclinic' according to /home/saulius/struct/CIF-dictionaries/cif_core.dic dictionary named 'cif_core.dic' version 2.4.1 from 2010-06-29. Automatic conversion script Id: cif_fix_values 1715 2011-07-08 13:25:40Z adriana ; _cod_database_code 2204098 _cod_database_fobs_code 2204098 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' 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_type_symbol S1 0.71528(8) 0.29972(9) 0.23854(6) 0.0497(2) Uani d . 1 S O1 0.7606(2) 0.4533(2) 0.27705(17) 0.0699(6) Uani d . 1 O O2 0.8216(2) 0.2391(3) 0.24615(18) 0.0707(7) Uani d . 1 O O3 0.3755(2) 0.0346(2) -0.01740(16) 0.0494(5) Uani d . 1 O O4 0.7045(2) 0.4956(3) -0.39457(16) 0.0672(6) Uani d . 1 O N1 0.6584(2) 0.2737(2) 0.10482(17) 0.0423(5) Uani d . 1 N H1 0.6812 0.2164 0.0591 0.051 Uiso calc R 1 H C1 0.5590(3) 0.1879(3) 0.3134(2) 0.0431(6) Uani d . 1 C C2 0.4877(4) 0.2528(4) 0.3800(2) 0.0587(8) Uani d . 1 C H2 0.5242 0.3575 0.3889 0.070 Uiso calc R 1 H C3 0.3613(4) 0.1606(4) 0.4335(2) 0.0672(9) Uani d . 1 C H3 0.3122 0.2044 0.4774 0.081 Uiso calc R 1 H C4 0.3064(3) 0.0060(4) 0.4234(3) 0.0629(9) Uani d . 1 C C5 0.3799(4) -0.0560(4) 0.3581(3) 0.0673(9) Uani d . 1 C H5 0.3447 -0.1605 0.3510 0.081 Uiso calc R 1 H C6 0.5048(3) 0.0329(3) 0.3026(3) 0.0575(8) Uani d . 1 C H6 0.5527 -0.0116 0.2579 0.069 Uiso calc R 1 H C7 0.1688(4) -0.0940(5) 0.4832(3) 0.1026(15) Uani d . 1 C H7A 0.1208 -0.0351 0.5134 0.154 Uiso calc R 1 H H7B 0.1998 -0.1350 0.5447 0.154 Uiso calc R 1 H H7C 0.0985 -0.1752 0.4295 0.154 Uiso calc R 1 H C8 0.5690(3) 0.3446(3) 0.0585(2) 0.0384(6) Uani d . 1 C H8 0.6085 0.4446 0.1019 0.046 Uiso calc R 1 H C9 0.6047(3) 0.3756(3) -0.0646(2) 0.0355(6) Uani d . 1 C C10 0.7542(3) 0.4607(3) -0.0889(2) 0.0399(6) Uani d . 1 C H10 0.8306 0.4905 -0.0303 0.048 Uiso calc R 1 H C11 0.7938(3) 0.5026(3) -0.1972(2) 0.0418(6) Uani d . 1 C H11 0.8951 0.5591 -0.2111 0.050 Uiso calc R 1 H C12 0.6808(3) 0.4597(3) -0.2847(2) 0.0446(7) Uani d . 1 C C13 0.5307(3) 0.3752(3) -0.2618(2) 0.0510(7) Uani d . 1 C H13 0.4539 0.3471 -0.3199 0.061 Uiso calc R 1 H C14 0.4942(3) 0.3326(3) -0.1537(2) 0.0440(7) Uani d . 1 C H14 0.3931 0.2736 -0.1404 0.053 Uiso calc R 1 H C15 0.8561(4) 0.5762(5) -0.4235(3) 0.0847(12) Uani d . 1 C H15A 0.9034 0.6736 -0.3796 0.127 Uiso calc R 1 H H15B 0.8568 0.5896 -0.5037 0.127 Uiso calc R 1 H H15C 0.9111 0.5202 -0.4070 0.127 Uiso calc R 1 H C16 0.3999(3) 0.2628(3) 0.0808(2) 0.0388(6) Uani d . 1 C H16A 0.3906 0.2813 0.1617 0.047 Uiso calc R 1 H H16B 0.3469 0.3080 0.0391 0.047 Uiso calc R 1 H C17 0.3209(3) 0.0941(3) 0.0480(2) 0.0371(6) Uani d . 1 C C18 0.1777(3) 0.0027(3) 0.1024(2) 0.0393(6) Uani d . 1 C C19 0.0906(3) 0.0655(3) 0.1495(2) 0.0508(7) Uani d . 1 C H19 0.1187 0.1679 0.1461 0.061 Uiso calc R 1 H C20 -0.0388(3) -0.0240(4) 0.2018(3) 0.0640(9) Uani d . 1 C H20 -0.0993 0.0177 0.2312 0.077 Uiso calc R 1 H C21 -0.0780(3) -0.1734(4) 0.2104(3) 0.0613(9) Uani d . 1 C H21 -0.1631 -0.2321 0.2480 0.074 Uiso calc R 1 H C22 0.0078(3) -0.2372(4) 0.1638(3) 0.0623(9) Uani d . 1 C H22 -0.0191 -0.3389 0.1694 0.075 Uiso calc R 1 H C23 0.1334(3) -0.1501(3) 0.1089(3) 0.0555(8) Uani d . 1 C H23 0.1898 -0.1943 0.0754 0.067 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 S1 0.0399(4) 0.0526(5) 0.0439(4) 0.0083(3) 0.0025(3) 0.0143(3) O1 0.0763(15) 0.0485(13) 0.0558(13) 0.0019(11) 0.0024(11) 0.0106(10) O2 0.0417(11) 0.0996(18) 0.0738(15) 0.0312(12) 0.0045(10) 0.0319(13) O3 0.0516(11) 0.0417(11) 0.0602(12) 0.0242(9) 0.0214(9) 0.0072(9) O4 0.0568(13) 0.0836(16) 0.0410(11) 0.0123(11) 0.0078(9) 0.0157(10) N1 0.0445(12) 0.0479(13) 0.0397(12) 0.0241(11) 0.0104(10) 0.0119(10) C1 0.0411(15) 0.0472(17) 0.0367(14) 0.0153(13) 0.0032(11) 0.0100(12) C2 0.071(2) 0.0543(19) 0.0457(17) 0.0240(17) 0.0083(15) 0.0026(14) C3 0.068(2) 0.098(3) 0.0422(17) 0.041(2) 0.0145(15) 0.0099(17) C4 0.0482(17) 0.085(3) 0.0495(18) 0.0214(18) 0.0061(14) 0.0320(17) C5 0.058(2) 0.055(2) 0.084(2) 0.0181(17) 0.0106(18) 0.0293(18) C6 0.0566(18) 0.0512(19) 0.067(2) 0.0247(16) 0.0136(15) 0.0156(15) C7 0.061(2) 0.149(4) 0.084(3) 0.027(2) 0.023(2) 0.061(3) C8 0.0382(14) 0.0351(14) 0.0442(15) 0.0176(12) 0.0093(11) 0.0084(11) C9 0.0376(13) 0.0317(14) 0.0414(14) 0.0187(11) 0.0055(11) 0.0064(11) C10 0.0345(14) 0.0430(15) 0.0427(15) 0.0173(12) 0.0034(11) 0.0090(12) C11 0.0342(13) 0.0413(15) 0.0479(16) 0.0141(12) 0.0096(12) 0.0094(12) C12 0.0478(16) 0.0438(16) 0.0407(15) 0.0184(13) 0.0096(12) 0.0072(12) C13 0.0418(15) 0.0604(19) 0.0412(16) 0.0146(14) -0.0029(12) 0.0080(13) C14 0.0323(13) 0.0417(16) 0.0508(16) 0.0095(12) 0.0049(12) 0.0108(12) C15 0.063(2) 0.114(3) 0.051(2) 0.013(2) 0.0228(17) 0.0234(19) C16 0.0397(14) 0.0384(15) 0.0429(14) 0.0203(12) 0.0119(11) 0.0097(11) C17 0.0374(13) 0.0406(15) 0.0389(14) 0.0214(12) 0.0071(11) 0.0115(11) C18 0.0324(13) 0.0442(16) 0.0414(15) 0.0166(12) 0.0044(11) 0.0098(12) C19 0.0441(16) 0.0525(18) 0.0612(18) 0.0244(14) 0.0154(13) 0.0163(14) C20 0.0477(17) 0.082(3) 0.072(2) 0.0363(18) 0.0209(15) 0.0154(18) C21 0.0336(15) 0.074(2) 0.065(2) 0.0120(16) 0.0113(14) 0.0227(17) C22 0.0500(17) 0.0484(19) 0.078(2) 0.0107(15) 0.0135(16) 0.0183(16) C23 0.0473(16) 0.0451(18) 0.073(2) 0.0180(14) 0.0192(15) 0.0147(15) 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 _geom_angle_publ_flag O1 S1 O2 120.06(15) yes O1 S1 N1 107.86(12) yes O2 S1 N1 105.50(13) yes O1 S1 C1 107.74(14) yes O2 S1 C1 107.40(13) yes N1 S1 C1 107.75(12) yes C12 O4 C15 118.0(2) ? C8 N1 S1 122.13(18) yes C8 N1 H1 118.9 ? S1 N1 H1 118.9 ? C2 C1 C6 119.7(3) ? C2 C1 S1 120.9(2) ? C6 C1 S1 119.4(2) ? C1 C2 C3 119.2(3) ? C1 C2 H2 120.4 ? C3 C2 H2 120.4 ? C4 C3 C2 121.7(3) ? C4 C3 H3 119.1 ? C2 C3 H3 119.1 ? C5 C4 C3 118.2(3) ? C5 C4 C7 120.5(4) ? C3 C4 C7 121.3(4) ? C4 C5 C6 121.4(3) ? C4 C5 H5 119.3 ? C6 C5 H5 119.3 ? C5 C6 C1 119.9(3) ? C5 C6 H6 120.1 ? C1 C6 H6 120.1 ? C4 C7 H7A 109.5 ? C4 C7 H7B 109.5 ? H7A C7 H7B 109.5 ? C4 C7 H7C 109.5 ? H7A C7 H7C 109.5 ? H7B C7 H7C 109.5 ? N1 C8 C9 109.68(19) ? N1 C8 C16 113.49(19) ? C9 C8 C16 116.4(2) ? N1 C8 H8 105.4 ? C9 C8 H8 105.4 ? C16 C8 H8 105.4 ? C14 C9 C10 117.3(2) ? C14 C9 C8 123.2(2) ? C10 C9 C8 119.3(2) ? C11 C10 C9 122.4(2) ? C11 C10 H10 118.8 ? C9 C10 H10 118.8 ? C10 C11 C12 119.2(2) ? C10 C11 H11 120.4 ? C12 C11 H11 120.4 ? O4 C12 C11 124.9(2) ? O4 C12 C13 115.9(2) ? C11 C12 C13 119.2(2) ? C14 C13 C12 120.6(2) ? C14 C13 H13 119.7 ? C12 C13 H13 119.7 ? C13 C14 C9 121.3(2) ? C13 C14 H14 119.3 ? C9 C14 H14 119.3 ? O4 C15 H15A 109.5 ? O4 C15 H15B 109.5 ? H15A C15 H15B 109.5 ? O4 C15 H15C 109.5 ? H15A C15 H15C 109.5 ? H15B C15 H15C 109.5 ? C17 C16 C8 116.0(2) ? C17 C16 H16A 108.3 ? C8 C16 H16A 108.3 ? C17 C16 H16B 108.3 ? C8 C16 H16B 108.3 ? H16A C16 H16B 107.4 ? O3 C17 C18 121.4(2) ? O3 C17 C16 120.7(2) ? C18 C17 C16 117.8(2) ? C19 C18 C23 118.8(2) ? C19 C18 C17 122.5(2) ? C23 C18 C17 118.7(2) ? C18 C19 C20 119.9(3) ? C18 C19 H19 120.0 ? C20 C19 H19 120.0 ? C21 C20 C19 120.3(3) ? C21 C20 H20 119.8 ? C19 C20 H20 119.8 ? C20 C21 C22 120.2(3) ? C20 C21 H21 119.9 ? C22 C21 H21 119.9 ? C23 C22 C21 119.7(3) ? C23 C22 H22 120.2 ? C21 C22 H22 120.2 ? C22 C23 C18 121.0(3) ? C22 C23 H23 119.5 ? C18 C23 H23 119.5 ? loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_publ_flag S1 O1 1.413(2) yes S1 O2 1.430(2) yes S1 N1 1.611(2) yes S1 C1 1.758(3) yes O3 C17 1.215(3) yes O4 C12 1.363(3) yes O4 C15 1.415(4) yes N1 C8 1.467(3) yes N1 H1 0.8600 ? C1 C2 1.376(4) ? C1 C6 1.377(4) ? C2 C3 1.380(4) ? C2 H2 0.9300 ? C3 C4 1.372(5) ? C3 H3 0.9300 ? C4 C5 1.365(5) ? C4 C7 1.511(4) ? C5 C6 1.375(4) ? C5 H5 0.9300 ? C6 H6 0.9300 ? C7 H7A 0.9600 ? C7 H7B 0.9600 ? C7 H7C 0.9600 ? C8 C9 1.520(3) ? C8 C16 1.537(3) ? C8 H8 0.9800 ? C9 C14 1.380(3) ? C9 C10 1.387(3) ? C10 C11 1.382(3) ? C10 H10 0.9300 ? C11 C12 1.383(4) ? C11 H11 0.9300 ? C12 C13 1.386(4) ? C13 C14 1.376(4) ? C13 H13 0.9300 ? C14 H14 0.9300 ? C15 H15A 0.9600 ? C15 H15B 0.9600 ? C15 H15C 0.9600 ? C16 C17 1.506(3) ? C16 H16A 0.9700 ? C16 H16B 0.9700 ? C17 C18 1.493(3) ? C18 C19 1.378(4) ? C18 C23 1.386(4) ? C19 C20 1.385(4) ? C19 H19 0.9300 ? C20 C21 1.367(4) ? C20 H20 0.9300 ? C21 C22 1.371(4) ? C21 H21 0.9300 ? C22 C23 1.370(4) ? C22 H22 0.9300 ? C23 H23 0.9300 ? 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 _geom_hbond_publ_flag N1 H1 O3 2_655 0.86 2.30 3.019(3) 141 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_publ_flag O1 S1 N1 C8 -39.4(2) yes O2 S1 N1 C8 -168.84(19) yes C1 S1 N1 C8 76.7(2) yes O1 S1 C1 C2 10.0(3) ? O2 S1 C1 C2 140.7(2) ? N1 S1 C1 C2 -106.1(2) ? O1 S1 C1 C6 -171.7(2) ? O2 S1 C1 C6 -41.1(3) ? N1 S1 C1 C6 72.1(2) ? C6 C1 C2 C3 -1.0(4) ? S1 C1 C2 C3 177.2(2) ? C1 C2 C3 C4 1.1(5) ? C2 C3 C4 C5 -0.2(5) ? C2 C3 C4 C7 179.4(3) ? C3 C4 C5 C6 -0.6(5) ? C7 C4 C5 C6 179.7(3) ? C4 C5 C6 C1 0.6(5) ? C2 C1 C6 C5 0.2(4) ? S1 C1 C6 C5 -178.1(2) ? S1 N1 C8 C9 148.75(18) yes S1 N1 C8 C16 -79.2(3) yes N1 C8 C9 C14 129.8(2) ? C16 C8 C9 C14 -0.8(3) ? N1 C8 C9 C10 -55.1(3) ? C16 C8 C9 C10 174.4(2) ? C14 C9 C10 C11 0.3(4) ? C8 C9 C10 C11 -175.1(2) ? C9 C10 C11 C12 0.5(4) ? C15 O4 C12 C11 3.4(4) ? C15 O4 C12 C13 -177.4(3) ? C10 C11 C12 O4 179.0(2) ? C10 C11 C12 C13 -0.2(4) ? O4 C12 C13 C14 179.9(3) ? C11 C12 C13 C14 -0.9(4) ? C12 C13 C14 C9 1.7(4) ? C10 C9 C14 C13 -1.4(4) ? C8 C9 C14 C13 173.8(2) ? N1 C8 C16 C17 -50.6(3) yes C9 C8 C16 C17 78.1(3) ? C8 C16 C17 O3 -18.0(3) yes C8 C16 C17 C18 159.4(2) yes O3 C17 C18 C19 -161.1(2) ? C16 C17 C18 C19 21.5(3) ? O3 C17 C18 C23 20.9(4) ? C16 C17 C18 C23 -156.5(2) ? C23 C18 C19 C20 -0.1(4) ? C17 C18 C19 C20 -178.1(3) ? C18 C19 C20 C21 2.2(5) ? C19 C20 C21 C22 -2.2(5) ? C20 C21 C22 C23 0.2(5) ? C21 C22 C23 C18 1.8(5) ? C19 C18 C23 C22 -1.8(4) ? C17 C18 C23 C22 176.2(3) ?