#------------------------------------------------------------------------------
#$Date: 2011-09-10 04:16:28 +0100 (Sat, 10 Sep 2011) $
#$Revision: 25271 $
#$URL: svn://www.crystallography.net/cod/cif/2/2007357.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_2007357
loop_
_publ_author_name
'Kumar, M. S.'
'Ponnuswamy, M. N.'
'Ponnuswamy, S.'
'Jeyaraman, R.'
'Paneerselvam, K.'
'Soriano-Garcia, M.'
_publ_section_title
;
 Ethyl
 3,5-Dimethyl-4-oxo-<i>cis</i>-2,6-diphenylpiperidine-1-carboxylate
;
_journal_issue                   6
_journal_name_full               'Acta Crystallographica Section C'
_journal_page_first              870
_journal_page_last               872
_journal_volume                  54
_journal_year                    1998
_chemical_formula_moiety         'C22 H25 N O3'
_chemical_formula_sum            'C22 H25 N O3'
_chemical_formula_weight         351.43
_chemical_melting_point          67
_chemical_name_systematic
;
 N-ethoxycarbonyl-3,5-dimethyl-cis-2,6-diphenyl piperidin-4-one
;
_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           SHELXL
_cell_angle_alpha                90.00
_cell_angle_beta                 95.70(2)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   10.404(2)
_cell_length_b                   9.743(2)
_cell_length_c                   19.096(3)
_cell_measurement_reflns_used    20
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      18
_cell_measurement_theta_min      10
_cell_volume                     1926.1(6)
_computing_cell_refinement       XSCANS
_computing_data_collection       'XSCANS (Siemens, 1992)'
_computing_data_reduction        XSCANS
_computing_molecular_graphics    'ZORTEP (Zsolnai, 1997)'
_computing_publication_material  'PARST (Nardelli, 1983, 1995)'
_computing_structure_refinement  'SHELXL93 (Sheldrick, 1993)'
_computing_structure_solution    'SHELXS86 (Sheldrick, 1990)'
_diffrn_ambient_temperature      293(2)
_diffrn_measurement_device       'Siemens P4'
_diffrn_measurement_method       \w/2\q
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.016
_diffrn_reflns_av_sigmaI/netI    0.027
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       0
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_limit_l_min       0
_diffrn_reflns_number            3244
_diffrn_reflns_theta_max         62.49
_diffrn_reflns_theta_min         4.65
_diffrn_standards_decay_%        <1
_diffrn_standards_interval_count 200
_diffrn_standards_interval_time  60
_diffrn_standards_number         3
_exptl_absorpt_coefficient_mu    0.639
_exptl_absorpt_correction_T_max  0.826
_exptl_absorpt_correction_T_min  0.717
_exptl_absorpt_correction_type   'CYLABS (Nardelli, 1997)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.212
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       'thick plate'
_exptl_crystal_F_000             752
_exptl_crystal_size_max          0.6
_exptl_crystal_size_mid          0.5
_exptl_crystal_size_min          0.3
_refine_diff_density_max         0.182
_refine_diff_density_min         -0.200
_refine_ls_extinction_coef       0.0087(9)
_refine_ls_extinction_method     SHELXL93
_refine_ls_goodness_of_fit_all   1.030
_refine_ls_goodness_of_fit_obs   1.031
_refine_ls_hydrogen_treatment    'H atoms constrained'
_refine_ls_matrix_type           full
_refine_ls_number_parameters     239
_refine_ls_number_reflns         3055
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.047
_refine_ls_restrained_S_obs      1.031
_refine_ls_R_factor_all          0.063
_refine_ls_R_factor_obs          0.050
_refine_ls_shift/esd_max         0.000
_refine_ls_shift/esd_mean        0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_scheme
'calc w = 1/[\s^2^(Fo^2^)+(0.07P)^2^+0.9P] where P = (Fo^2^+2Fc^2^)/3'
_refine_ls_wR_factor_all         0.157
_refine_ls_wR_factor_obs         0.138
_reflns_number_observed          2495
_reflns_number_total             3058
_reflns_observed_criterion       I>2\s(I)
_[local]_cod_data_source_file    na1307.cif
_[local]_cod_data_source_block   sur
_[local]_cod_cif_authors_sg_H-M  'P 21/n'
_cod_database_code               2007357
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_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 0.0437(9) 0.0516(10) 0.0445(9) -0.0112(8) 0.0103(7) -0.0091(7)
C2 0.0459(11) 0.0467(12) 0.0432(11) -0.0035(9) 0.0076(9) -0.0019(9)
C3 0.0462(12) 0.0513(12) 0.0455(11) -0.0035(9) 0.0008(9) -0.0044(9)
C4 0.0462(12) 0.0646(15) 0.0578(13) -0.0044(11) 0.0009(10) -0.0029(11)
C5 0.0512(13) 0.0572(14) 0.0617(14) -0.0009(10) 0.0109(11) -0.0033(11)
C6 0.0511(12) 0.0533(13) 0.0463(11) -0.0092(10) 0.0113(9) -0.0086(9)
C7 0.0559(13) 0.0537(13) 0.0418(11) -0.0101(10) 0.0106(9) -0.0026(9)
C8 0.0628(15) 0.0617(15) 0.0602(14) -0.0158(12) 0.0012(11) 0.0006(11)
C9 0.093(2) 0.059(2) 0.072(2) -0.0261(15) 0.0085(15) -0.0017(13)
C10 0.099(2) 0.061(2) 0.073(2) -0.005(2) 0.015(2) 0.0084(13)
C11 0.091(2) 0.075(2) 0.073(2) 0.001(2) -0.001(2) 0.0207(15)
C12 0.073(2) 0.070(2) 0.0607(14) -0.0132(13) -0.0039(12) 0.0051(12)
C13 0.0397(11) 0.0579(13) 0.0433(11) -0.0031(9) 0.0048(9) -0.0061(9)
C14 0.0622(15) 0.068(2) 0.0605(14) -0.0087(12) 0.0191(12) -0.0028(12)
C15 0.057(2) 0.104(2) 0.080(2) -0.017(2) 0.0286(14) -0.017(2)
C16 0.0508(14) 0.109(3) 0.084(2) 0.007(2) 0.0120(13) -0.022(2)
C17 0.070(2) 0.087(2) 0.086(2) 0.023(2) 0.0033(15) -0.002(2)
C18 0.0568(14) 0.064(2) 0.0685(15) 0.0056(12) 0.0103(11) 0.0041(12)
C19 0.0496(12) 0.0493(12) 0.0506(12) -0.0067(10) 0.0090(10) -0.0084(10)
O20 0.0669(10) 0.0619(10) 0.0600(10) -0.0247(8) 0.0117(8) -0.0101(8)
O21 0.0793(12) 0.0839(12) 0.0509(9) -0.0366(10) 0.0177(8) -0.0237(8)
C22 0.067(2) 0.089(2) 0.0643(15) -0.0262(14) 0.0053(13) -0.0333(14)
C23 0.089(2) 0.079(2) 0.0581(15) 0.009(2) -0.0005(14) -0.0168(13)
C24 0.0638(15) 0.082(2) 0.0481(13) -0.0026(13) 0.0025(11) -0.0064(12)
C25 0.085(2) 0.066(2) 0.089(2) 0.0171(15) 0.017(2) -0.0018(14)
O26 0.0549(11) 0.166(2) 0.0697(12) 0.0000(13) -0.0116(9) -0.0152(13)
loop_
_atom_site_label
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_thermal_displace_type
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_occupancy
_atom_site_type_symbol
N1 0.7325(2) 0.3027(2) 0.59282(9) 0.0462(5) Uani d . 1 N
C2 0.7062(2) 0.3038(2) 0.66789(10) 0.0451(5) Uani d . 1 C
H2 0.7121(2) 0.2090(2) 0.68499(10) 0.054 Uiso calc R 1 H
C3 0.8085(2) 0.3888(2) 0.71297(10) 0.0479(5) Uani d . 1 C
H3 0.7950(2) 0.4852(2) 0.69964(10) 0.058 Uiso calc R 1 H
C4 0.9450(2) 0.3515(3) 0.69875(12) 0.0565(6) Uani d . 1 C
C5 0.9658(2) 0.3088(2) 0.62480(12) 0.0563(6) Uani d . 1 C
H5 1.0464(2) 0.3501(2) 0.61256(12) 0.068 Uiso calc R 1 H
C6 0.8557(2) 0.3591(2) 0.57223(11) 0.0498(6) Uani d . 1 C
H6 0.8692(2) 0.3177(2) 0.52676(11) 0.060 Uiso calc R 1 H
C7 0.8470(2) 0.5143(2) 0.56030(11) 0.0501(5) Uani d . 1 C
C8 0.9389(2) 0.6059(3) 0.58980(12) 0.0619(6) Uani d . 1 C
H8 1.0099(2) 0.5730(3) 0.61829(12) 0.074 Uiso calc R 1 H
C9 0.9264(3) 0.7460(3) 0.57743(15) 0.0746(8) Uani d . 1 C
H9 0.9889(3) 0.8058(3) 0.59791(15) 0.090 Uiso calc R 1 H
C10 0.8237(3) 0.7968(3) 0.53566(15) 0.0774(8) Uani d . 1 C
H10 0.8150(3) 0.8909(3) 0.52836(15) 0.093 Uiso calc R 1 H
C11 0.7329(3) 0.7077(3) 0.5044(2) 0.0804(8) Uani d . 1 C
H11 0.6634(3) 0.7412(3) 0.4749(2) 0.096 Uiso calc R 1 H
C12 0.7450(3) 0.5679(3) 0.51681(13) 0.0685(7) Uani d . 1 C
H12 0.6830(3) 0.5087(3) 0.49537(13) 0.082 Uiso calc R 1 H
C13 0.5712(2) 0.3554(2) 0.67672(10) 0.0469(5) Uani d . 1 C
C14 0.4846(2) 0.2737(3) 0.70866(13) 0.0628(7) Uani d . 1 C
H14 0.5086(2) 0.1854(3) 0.72305(13) 0.075 Uiso calc R 1 H
C15 0.3631(3) 0.3217(4) 0.7194(2) 0.0789(9) Uani d . 1 C
H15 0.3062(3) 0.2652(4) 0.7406(2) 0.095 Uiso calc R 1 H
C16 0.3260(3) 0.4505(4) 0.6993(2) 0.0807(9) Uani d . 1 C
H16 0.2446(3) 0.4827(4) 0.7072(2) 0.097 Uiso calc R 1 H
C17 0.4093(3) 0.5327(3) 0.6672(2) 0.0811(8) Uani d . 1 C
H17 0.3838(3) 0.6207(3) 0.6529(2) 0.097 Uiso calc R 1 H
C18 0.5324(2) 0.4855(3) 0.65557(13) 0.0629(6) Uani d . 1 C
H18 0.5881(2) 0.5420(3) 0.63356(13) 0.076 Uiso calc R 1 H
C19 0.6602(2) 0.2099(2) 0.55217(11) 0.0496(5) Uani d . 1 C
O20 0.5783(2) 0.1383(2) 0.57364(8) 0.0626(5) Uani d . 1 O
O21 0.6921(2) 0.2078(2) 0.48566(8) 0.0706(6) Uani d . 1 O
C22 0.6220(3) 0.1096(3) 0.43870(14) 0.0737(8) Uani d . 1 C
H22A 0.5464(3) 0.1529(3) 0.41431(14) 0.088 Uiso calc R 1 H
H22B 0.5937(3) 0.0327(3) 0.46551(14) 0.088 Uiso calc R 1 H
C23 0.7082(3) 0.0618(3) 0.38795(13) 0.0760(8) Uani d . 1 C
H23A 0.6631(7) -0.0021(16) 0.3561(7) 0.114 Uiso calc R 1 H
H23B 0.7818(10) 0.0173(19) 0.4124(2) 0.114 Uiso calc R 1 H
H23C 0.7365(15) 0.1386(4) 0.3620(7) 0.114 Uiso calc R 1 H
C24 0.7903(3) 0.3772(3) 0.79114(12) 0.0650(7) Uani d . 1 C
H24A 0.7061(7) 0.4104(18) 0.7991(2) 0.097 Uiso calc R 1 H
H24B 0.8549(11) 0.4309(16) 0.81800(14) 0.097 Uiso calc R 1 H
H24C 0.7983(18) 0.2828(4) 0.8054(3) 0.097 Uiso calc R 1 H
C25 0.9803(3) 0.1523(3) 0.6233(2) 0.0792(8) Uani d . 1 C
H25A 0.999(2) 0.1239(4) 0.5771(4) 0.119 Uiso calc R 1 H
H25B 0.9015(8) 0.1101(3) 0.6345(11) 0.119 Uiso calc R 1 H
H25C 1.0499(14) 0.1249(3) 0.6571(8) 0.119 Uiso calc R 1 H
O26 1.0337(2) 0.3558(3) 0.74452(11) 0.0980(8) Uani d . 1 O
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'
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
C19 N1 C2 114.1(2) yes
C19 N1 C6 122.4(2) yes
C2 N1 C6 120.0(2) yes
N1 C2 C13 111.8(2) ?
N1 C2 C3 111.1(2) ?
C13 C2 C3 110.8(2) yes
N1 C2 H2 107.65(11) ?
C13 C2 H2 107.65(11) ?
C3 C2 H2 107.65(12) ?
C4 C3 C24 111.5(2) ?
C4 C3 C2 112.2(2) ?
C24 C3 C2 111.1(2) ?
C4 C3 H3 107.24(13) ?
C24 C3 H3 107.24(13) ?
C2 C3 H3 107.24(12) ?
O26 C4 C3 121.6(2) ?
O26 C4 C5 121.1(2) ?
C3 C4 C5 117.2(2) ?
C4 C5 C6 111.0(2) ?
C4 C5 C25 108.4(2) ?
C6 C5 C25 112.1(2) ?
C4 C5 H5 108.40(12) ?
C6 C5 H5 108.40(12) ?
C25 C5 H5 108.40(15) ?
N1 C6 C7 111.4(2) ?
N1 C6 C5 108.6(2) ?
C7 C6 C5 116.4(2) ?
N1 C6 H6 106.63(10) ?
C7 C6 H6 106.63(11) ?
C5 C6 H6 106.63(12) ?
C12 C7 C8 117.3(2) ?
C12 C7 C6 119.5(2) ?
C8 C7 C6 123.2(2) ?
C9 C8 C7 121.0(3) ?
C9 C8 H8 119.5(2) ?
C7 C8 H8 119.52(15) ?
C10 C9 C8 120.8(3) ?
C10 C9 H9 119.6(2) ?
C8 C9 H9 119.6(2) ?
C9 C10 C11 119.4(3) ?
C9 C10 H10 120.3(2) ?
C11 C10 H10 120.3(2) ?
C10 C11 C12 119.9(3) ?
C10 C11 H11 120.0(2) ?
C12 C11 H11 120.0(2) ?
C7 C12 C11 121.7(3) ?
C7 C12 H12 119.16(14) ?
C11 C12 H12 119.2(2) ?
C18 C13 C14 118.2(2) ?
C18 C13 C2 121.3(2) ?
C14 C13 C2 120.5(2) ?
C13 C14 C15 120.9(3) ?
C13 C14 H14 119.53(15) ?
C15 C14 H14 119.5(2) ?
C16 C15 C14 120.6(3) ?
C16 C15 H15 119.7(2) ?
C14 C15 H15 119.7(2) ?
C15 C16 C17 119.5(3) ?
C15 C16 H16 120.2(2) ?
C17 C16 H16 120.2(2) ?
C16 C17 C18 120.6(3) ?
C16 C17 H17 119.7(2) ?
C18 C17 H17 119.7(2) ?
C13 C18 C17 120.1(3) ?
C13 C18 H18 119.94(13) ?
C17 C18 H18 119.9(2) ?
O20 C19 O21 124.2(2) yes
O20 C19 N1 123.9(2) yes
O21 C19 N1 111.9(2) yes
C19 O21 C22 115.9(2) yes
O21 C22 C23 108.4(2) ?
O21 C22 H22A 110.0(2) ?
C23 C22 H22A 110.0(2) ?
O21 C22 H22B 110.02(14) ?
C23 C22 H22B 110.0(2) ?
H22A C22 H22B 108.4 ?
C22 C23 H23A 109.47(15) ?
C22 C23 H23B 109.5(2) ?
H23A C23 H23B 109.5 ?
C22 C23 H23C 109.5(2) ?
H23A C23 H23C 109.5 ?
H23B C23 H23C 109.5 ?
C3 C24 H24A 109.47(13) ?
C3 C24 H24B 109.47(12) ?
H24A C24 H24B 109.5 ?
C3 C24 H24C 109.47(13) ?
H24A C24 H24C 109.5 ?
H24B C24 H24C 109.5 ?
C5 C25 H25A 109.47(15) ?
C5 C25 H25B 109.47(15) ?
H25A C25 H25B 109.5 ?
C5 C25 H25C 109.5(2) ?
H25A C25 H25C 109.5 ?
H25B C25 H25C 109.5 ?
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_publ_flag
N1 C19 1.367(3) yes
N1 C2 1.486(2) yes
N1 C6 1.483(3) yes
C2 C13 1.517(3) ?
C2 C3 1.542(3) ?
C2 H2 0.98 ?
C3 C4 1.516(3) ?
C3 C24 1.527(3) ?
C3 H3 0.98 ?
C4 O26 1.208(3) yes
C4 C5 1.508(3) ?
C5 C6 1.527(3) ?
C5 C25 1.533(4) ?
C5 H5 0.98 ?
C6 C7 1.531(3) ?
C6 H6 0.98 ?
C7 C12 1.383(3) ?
C7 C8 1.386(3) ?
C8 C9 1.389(4) ?
C8 H8 0.93 ?
C9 C10 1.362(4) ?
C9 H9 0.93 ?
C10 C11 1.375(4) ?
C10 H10 0.93 ?
C11 C12 1.386(4) ?
C11 H11 0.93 ?
C12 H12 0.93 ?
C13 C18 1.378(3) ?
C13 C14 1.388(3) ?
C14 C15 1.382(4) ?
C14 H14 0.93 ?
C15 C16 1.357(4) ?
C15 H15 0.93 ?
C16 C17 1.368(4) ?
C16 H16 0.93 ?
C17 C18 1.399(4) ?
C17 H17 0.93 ?
C18 H18 0.93 ?
C19 O20 1.204(3) yes
C19 O21 1.344(3) yes
O21 C22 1.456(3) yes
C22 C23 1.461(4) ?
C22 H22A 0.97 ?
C22 H22B 0.97 ?
C23 H23A 0.96 ?
C23 H23B 0.96 ?
C23 H23C 0.96 ?
C24 H24A 0.96 ?
C24 H24B 0.96 ?
C24 H24C 0.96 ?
C25 H25A 0.96 ?
C25 H25B 0.96 ?
C25 H25C 0.96 ?
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
C19 N1 C2 C13 -66.9(2) yes
C6 N1 C2 C13 133.7(2) ?
C19 N1 C2 C3 168.7(2) ?
C6 N1 C2 C3 9.3(3) yes
N1 C2 C3 C4 -48.2(2) yes
C13 C2 C3 C4 -173.1(2) ?
N1 C2 C3 C24 -173.8(2) ?
C13 C2 C3 C24 61.3(2) yes
C24 C3 C4 O26 -21.5(3) ?
C2 C3 C4 O26 -146.9(3) ?
C24 C3 C4 C5 158.6(2) ?
C2 C3 C4 C5 33.2(3) yes
O26 C4 C5 C6 -159.6(2) ?
C3 C4 C5 C6 20.3(3) yes
O26 C4 C5 C25 76.8(3) ?
C3 C4 C5 C25 -103.2(3) ?
C19 N1 C6 C7 116.6(2) ?
C2 N1 C6 C7 -85.7(2) ?
C19 N1 C6 C5 -113.9(2) ?
C2 N1 C6 C5 43.8(2) yes
C4 C5 C6 N1 -58.0(2) yes
C25 C5 C6 N1 63.4(2) ?
C4 C5 C6 C7 68.6(2) yes
C25 C5 C6 C7 -170.0(2) ?
N1 C6 C7 C12 -50.7(3) ?
C5 C6 C7 C12 -176.0(2) ?
N1 C6 C7 C8 130.9(2) ?
C5 C6 C7 C8 5.7(3) ?
C12 C7 C8 C9 1.7(4) ?
C6 C7 C8 C9 -179.9(2) ?
C7 C8 C9 C10 -0.3(4) ?
C8 C9 C10 C11 -1.3(4) ?
C9 C10 C11 C12 1.5(4) ?
C8 C7 C12 C11 -1.5(4) ?
C6 C7 C12 C11 -180.0(2) ?
C10 C11 C12 C7 0.0(4) ?
N1 C2 C13 C18 -60.4(3) ?
C3 C2 C13 C18 64.1(3) ?
N1 C2 C13 C14 121.8(2) ?
C3 C2 C13 C14 -113.7(2) ?
C18 C13 C14 C15 -0.4(4) ?
C2 C13 C14 C15 177.5(2) ?
C13 C14 C15 C16 -0.5(4) ?
C14 C15 C16 C17 0.9(4) ?
C15 C16 C17 C18 -0.6(5) ?
C14 C13 C18 C17 0.7(3) ?
C2 C13 C18 C17 -177.2(2) ?
C16 C17 C18 C13 -0.2(4) ?
C2 N1 C19 O20 2.9(3) ?
C6 N1 C19 O20 161.7(2) ?
C2 N1 C19 O21 -176.8(2) yes
C6 N1 C19 O21 -18.0(3) ?
O20 C19 O21 C22 -1.0(4) ?
N1 C19 O21 C22 178.7(2) yes
C19 O21 C22 C23 -147.4(2) ?