##############################################################################
###                                                                        ###
###        Electronic paper (Acta Crystallographica Section E)             ###
###                                                                        ###
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#                                                                            #
# This CIF contains the data in a paper accepted for publication in Acta     #
# Crystallographica Section E. It conforms to the requirements of Notes      #
# for Authors for Section E, and has been peer reviewed under the auspices   #
# of the IUCr Commission on Journals.                                        #
#                                                                            #
# Full details of the Crystallographic Information File format               #
# are given in the paper "The Crystallographic Information File (CIF):       #
# a New Standard Archive File for Crystallography" by S. R. Hall, F. H.      #
# Allen and I. D. Brown [Acta Cryst. (1991), A47, 655-685].                  #
#                                                                            #
# The current version of the core CIF dictionary is obtainable from          #
# ftp://ftp.iucr.org/pub/cif_core.dic. The current version number is 2.1.    #
#                                                                            #
# Software is freely available for graphical display of the structure(s) in  #
# this CIF.  For information consult the CIF home page http://www.iucr.org/  #
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##############################################################################
                                             
data_global
_audit_creation_method     'SHELXL-97'
_journal_date_recd_electronic     2006-03-29
_journal_date_accepted     2006-03-31
_journal_name_full     'Acta Crystallographica, Section E'
_journal_year     2006
_journal_volume     62
_journal_issue      5
_journal_page_first     o1713
_journal_page_last     o1714
_journal_paper_category     EO
_journal_coeditor_code     CI2043
_publ_contact_author_name     'Shu-Rong Ban'
_publ_contact_author_address
;
State Key Laboratory and Institute of Elemento-Organic Chemistry
Nankai University
Tianjin
Weijin road No 94, Tianjin
China
;
_publ_contact_author_email     banshurong@syn.nankai.edu.cn
_publ_contact_author_fax     86-22-23504782
_publ_contact_author_phone     86-22-23504782
_publ_section_title
;
N-(3-Benzyloxy-5-methylpyrazin-2-yl)-2-chlorobenzenesulfonamide
;
loop_
    _publ_author_name
    _publ_author_footnote
    _publ_author_address
    'Shu-Rong Ban' .
;
State Key Laboratory and Institute of Elemento-Organic Chemistry
Nankai University
Tianjin
Weijin Road No. 94, Tianjin
People's Republic of China
;
    'Xing Yang' .
;
State Key Laboratory and Institute of Elemento-Organic Chemistry
Nankai University
Tianjin
Weijin Road No. 94, Tianjin
People's Republic of China
;
    'Wen-Bin Chen' .
;
State Key Laboratory and Institute of Elemento-Organic Chemistry
Nankai University
Tianjin
Weijin Road No. 94, Tianjin
People's Republic of China
;
    'Xiao-Feng Cheng' .
;
State Key Laboratory and Institute of Elemento-Organic Chemistry
Nankai University
Tianjin
Weijin Road No. 94, Tianjin
People's Republic of China
;
    'Hai-Bin Song' .
;
State Key Laboratory and Institute of Elemento-Organic Chemistry
Nankai University
Tianjin
Weijin Road No. 94, Tianjin
People's Republic of China
;
data_I
_chemical_name_systematic
;
N-(3-benzyloxy-5-methylpyrazin-2-yl)-2-chloro-benzenesulfonamide
;
_chemical_name_common     ?
_chemical_formula_moiety     'C18 H16 Cl N3 O3 S'
_chemical_formula_sum     'C18 H16 Cl N3 O3 S'
_chemical_formula_iupac     'C18 H16 Cl N3 O3 S'
_chemical_formula_weight     389.85
_chemical_melting_point     ?
_symmetry_cell_setting     Monoclinic
_symmetry_space_group_name_H-M     'P 21/n'
_symmetry_space_group_name_Hall     '-P 2yn'
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'
_cell_length_a     11.764(3)
_cell_length_b     13.519(4)
_cell_length_c     12.068(4)
_cell_angle_alpha     90.00
_cell_angle_beta     107.466(5)
_cell_angle_gamma     90.00
_cell_volume     1830.7(9)
_cell_formula_units_Z     4
_cell_measurement_reflns_used     741
_cell_measurement_theta_min     2.32
_cell_measurement_theta_max     23.45
_cell_measurement_temperature     293(2)
_exptl_crystal_description     Prism
_exptl_crystal_colour     colourless
_exptl_crystal_size_max     0.26
_exptl_crystal_size_mid     0.22
_exptl_crystal_size_min     0.20
_exptl_crystal_density_diffrn     1.414
_exptl_crystal_density_meas     ?
_exptl_crystal_density_method     'not measured'
_exptl_crystal_F_000     808
_exptl_absorpt_coefficient_mu     0.346
_exptl_absorpt_correction_type     multi-scan
_exptl_absorpt_process_details     '(SADABS; Sheldrick, 1996)'
_exptl_absorpt_correction_T_min     0.9154
_exptl_absorpt_correction_T_max     0.9340
_exptl_special_details
;
;
_diffrn_ambient_temperature     293(2)
_diffrn_radiation_type     MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_source     'fine-focus sealed tube'
_diffrn_radiation_monochromator     graphite
_diffrn_measurement_device_type     'Bruker SMART 1000 CCD area-detector'
_diffrn_measurement_method     'φ and ω'
_diffrn_detector_area_resol_mean     ?
_diffrn_reflns_number     10398
_diffrn_reflns_av_R_equivalents     0.0501
_diffrn_reflns_av_sigmaI/netI     0.0634
_diffrn_reflns_theta_min     2.12
_diffrn_reflns_theta_max     26.41
_diffrn_reflns_theta_full     26.41
_diffrn_measured_fraction_theta_max     0.998
_diffrn_measured_fraction_theta_full     0.998
_diffrn_reflns_limit_h_min     -8
_diffrn_reflns_limit_h_max     14
_diffrn_reflns_limit_k_min     -16
_diffrn_reflns_limit_k_max     16
_diffrn_reflns_limit_l_min     -15
_diffrn_reflns_limit_l_max     14
_diffrn_standards_number     0
_diffrn_standards_interval_count     .
_diffrn_standards_interval_time     .
_diffrn_standards_decay_%     ?
_refine_special_details
;
 Refinement of F² against ALL reflections.  The weighted R-factor wR and
 goodness of fit S are based on F², conventional R-factors R are based
 on F, with F set to zero for negative F². The threshold expression of
 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is
 not relevant to the choice of reflections for refinement.  R-factors based
 on F² are statistically about twice as large as those based on F, and R-
 factors based on ALL data will be even larger.
;
_reflns_number_total     3745
_reflns_number_gt     2227
_reflns_threshold_expression     I>2σ(I)
_refine_ls_structure_factor_coef     Fsqd
_refine_ls_matrix_type     full
_refine_ls_R_factor_all     0.0953
_refine_ls_R_factor_gt     0.0450
_refine_ls_wR_factor_gt     0.0899
_refine_ls_wR_factor_ref     0.1062
_refine_ls_goodness_of_fit_ref     1.006
_refine_ls_restrained_S_all     1.006
_refine_ls_number_reflns     3745
_refine_ls_number_parameters     236
_refine_ls_number_restraints     0
_refine_ls_hydrogen_treatment     constr
_refine_ls_weighting_scheme     calc
_refine_ls_weighting_details
                 'calc w=1/[σ²(Fo²)+(0.0461P)²] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_hydrogens     geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary     difmap
_refine_ls_shift/su_max     0.002
_refine_ls_shift/su_mean     0.000
_refine_diff_density_max     0.241
_refine_diff_density_min     -0.316
_refine_ls_extinction_method     none
_refine_ls_extinction_coef     ?
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'
    'Cl' 'Cl' 0.1484 0.1585
                         'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
_computing_data_collection     'SMART (Bruker, 1998)'
_computing_cell_refinement     'SAINT (Bruker, 1999)'
_computing_data_reduction     'SAINT'
_computing_structure_solution     'SHELXS97 (Sheldrick, 1997)'
_computing_structure_refinement     'SHELXL97 (Sheldrick, 1997)'
_computing_molecular_graphics     'SHELXTL (Bruker, 1999)'
_computing_publication_material     'SHELXTL'
loop_
    _atom_site_type_symbol
    _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
    S S1 1.11173(6) 0.10591(5) 0.65465(6) 0.04022(18) Uani d . 1 . .
    Cl Cl1 0.88304(7) 0.17454(6) 0.44238(6) 0.0642(2) Uani d . 1 . .
    N N1 1.00012(19) 0.12341(15) 0.84574(18) 0.0456(5) Uani d . 1 . .
    N N2 0.81038(19) 0.00464(15) 0.85792(18) 0.0454(5) Uani d . 1 . .
    N N3 1.00358(19) 0.04077(14) 0.67572(17) 0.0433(5) Uani d . 1 . .
    H H3 0.9738 -0.0057 0.6270 0.052 Uiso calc R 1 . .
    O O1 0.81798(18) -0.06867(13) 0.68538(15) 0.0560(5) Uani d . 1 . .
    O O2 1.12520(16) 0.07065(13) 0.54749(15) 0.0508(5) Uani d . 1 . .
    O O3 1.21291(15) 0.10343(13) 0.75551(15) 0.0528(5) Uani d . 1 . .
    C C1 0.9557(2) 0.05524(18) 0.7677(2) 0.0388(6) Uani d . 1 . .
    C C2 0.8587(2) -0.00424(17) 0.7739(2) 0.0407(6) Uani d . 1 . .
    C C3 0.8562(2) 0.07508(19) 0.9390(2) 0.0442(7) Uani d . 1 . .
    C C4 0.9496(2) 0.13287(18) 0.9318(2) 0.0465(7) Uani d . 1 . .
    H H4 0.9794 0.1806 0.9887 0.056 Uiso calc R 1 . .
    C C5 0.7991(3) 0.0881(2) 1.0339(2) 0.0617(8) Uani d . 1 . .
    H H5A 0.7208 0.1155 1.0018 0.093 Uiso calc R 1 . .
    H H5B 0.8466 0.1321 1.0919 0.093 Uiso calc R 1 . .
    H H5C 0.7933 0.0251 1.0685 0.093 Uiso calc R 1 . .
    C C6 1.0591(2) 0.22972(17) 0.6365(2) 0.0365(6) Uani d . 1 . .
    C C7 0.9627(2) 0.25923(19) 0.5442(2) 0.0430(6) Uani d . 1 . .
    C C8 0.9248(3) 0.3566(2) 0.5342(3) 0.0588(8) Uani d . 1 . .
    H H8 0.8603 0.3762 0.4722 0.071 Uiso calc R 1 . .
    C C9 0.9834(3) 0.4242(2) 0.6168(3) 0.0664(9) Uani d . 1 . .
    H H9 0.9579 0.4896 0.6107 0.080 Uiso calc R 1 . .
    C C10 1.0798(3) 0.3960(2) 0.7087(3) 0.0619(8) Uani d . 1 . .
    H H10 1.1197 0.4424 0.7635 0.074 Uiso calc R 1 . .
    C C11 1.1166(2) 0.2989(2) 0.7186(2) 0.0524(7) Uani d . 1 . .
    H H11 1.1807 0.2796 0.7811 0.063 Uiso calc R 1 . .
    C C12 0.7486(3) -0.1525(2) 0.7025(3) 0.0587(8) Uani d . 1 . .
    H H12A 0.7001 -0.1769 0.6277 0.070 Uiso calc R 1 . .
    H H12B 0.6957 -0.1318 0.7462 0.070 Uiso calc R 1 . .
    C C13 0.8285(3) -0.23395(19) 0.7669(2) 0.0488(7) Uani d . 1 . .
    C C14 0.9298(3) -0.2587(3) 0.7390(3) 0.0751(10) Uani d . 1 . .
    H H14 0.9488 -0.2244 0.6802 0.090 Uiso calc R 1 . .
    C C15 1.0034(4) -0.3334(3) 0.7965(4) 0.0956(13) Uani d . 1 . .
    H H15 1.0720 -0.3487 0.7769 0.115 Uiso calc R 1 . .
    C C16 0.9764(4) -0.3848(3) 0.8819(4) 0.0922(12) Uani d . 1 . .
    H H16 1.0260 -0.4356 0.9205 0.111 Uiso calc R 1 . .
    C C17 0.8755(4) -0.3613(3) 0.9107(3) 0.0870(11) Uani d . 1 . .
    H H17 0.8565 -0.3963 0.9691 0.104 Uiso calc R 1 . .
    C C18 0.8018(3) -0.2860(2) 0.8533(3) 0.0662(9) Uani d . 1 . .
    H H18 0.7336 -0.2704 0.8736 0.079 Uiso calc R 1 . .
_geom_special_details
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
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 O3 . 1.4246(18) y
    S1 O2 . 1.4310(17) y
    S1 N3 . 1.629(2) y
    S1 C6 . 1.775(2) y
    Cl1 C7 . 1.734(3) ?
    N1 C1 . 1.309(3) y
    N1 C4 . 1.349(3) y
    N2 C2 . 1.308(3) y
    N2 C3 . 1.356(3) y
    N3 C1 . 1.401(3) y
    N3 H3 . 0.86 ?
    O1 C2 . 1.350(3) y
    O1 C12 . 1.447(3) y
    C1 C2 . 1.417(3) ?
    C3 C4 . 1.372(4) ?
    C3 C5 . 1.502(3) ?
    C4 H4 . 0.93 ?
    C5 H5A . 0.96 ?
    C5 H5B . 0.96 ?
    C5 H5C . 0.96 ?
    C6 C11 . 1.382(3) ?
    C6 C7 . 1.389(3) ?
    C7 C8 . 1.383(4) ?
    C8 C9 . 1.376(4) ?
    C8 H8 . 0.93 ?
    C9 C10 . 1.380(4) ?
    C9 H9 . 0.93 ?
    C10 C11 . 1.376(4) ?
    C10 H10 . 0.93 ?
    C11 H11 . 0.93 ?
    C12 C13 . 1.504(4) ?
    C12 H12A . 0.97 ?
    C12 H12B . 0.97 ?
    C13 C18 . 1.370(4) ?
    C13 C14 . 1.374(4) ?
    C14 C15 . 1.375(5) ?
    C14 H14 . 0.93 ?
    C15 C16 . 1.357(5) ?
    C15 H15 . 0.93 ?
    C16 C17 . 1.371(5) ?
    C16 H16 . 0.93 ?
    C17 C18 . 1.381(5) ?
    C17 H17 . 0.93 ?
    C18 H18 . 0.93 ?
loop_
    _geom_angle_atom_site_label_1
    _geom_angle_atom_site_label_2
    _geom_angle_atom_site_label_3
    _geom_angle_site_symmetry_1
    _geom_angle_site_symmetry_3
    _geom_angle
    _geom_angle_publ_flag
    O3 S1 O2 . . 118.26(11) y
    O3 S1 N3 . . 110.20(11) y
    O2 S1 N3 . . 105.34(11) y
    O3 S1 C6 . . 107.38(11) y
    O2 S1 C6 . . 109.35(11) y
    N3 S1 C6 . . 105.64(11) y
    C1 N1 C4 . . 116.6(2) ?
    C2 N2 C3 . . 116.9(2) y
    C1 N3 S1 . . 124.52(18) y
    C1 N3 H3 . . 117.7 ?
    S1 N3 H3 . . 117.7 ?
    C2 O1 C12 . . 118.3(2) ?
    N1 C1 N3 . . 120.0(2) ?
    N1 C1 C2 . . 121.0(2) ?
    N3 C1 C2 . . 119.0(2) ?
    N2 C2 O1 . . 122.7(2) y
    N2 C2 C1 . . 122.2(2) ?
    O1 C2 C1 . . 115.1(2) y
    N2 C3 C4 . . 120.5(2) ?
    N2 C3 C5 . . 117.4(2) ?
    C4 C3 C5 . . 122.1(3) ?
    N1 C4 C3 . . 122.7(2) ?
    N1 C4 H4 . . 118.6 ?
    C3 C4 H4 . . 118.6 ?
    C3 C5 H5A . . 109.5 ?
    C3 C5 H5B . . 109.5 ?
    H5A C5 H5B . . 109.5 ?
    C3 C5 H5C . . 109.5 ?
    H5A C5 H5C . . 109.5 ?
    H5B C5 H5C . . 109.5 ?
    C11 C6 C7 . . 119.1(2) ?
    C11 C6 S1 . . 118.2(2) ?
    C7 C6 S1 . . 122.74(19) ?
    C8 C7 C6 . . 120.5(2) ?
    C8 C7 Cl1 . . 118.4(2) ?
    C6 C7 Cl1 . . 121.1(2) ?
    C9 C8 C7 . . 119.4(3) ?
    C9 C8 H8 . . 120.3 ?
    C7 C8 H8 . . 120.3 ?
    C8 C9 C10 . . 120.8(3) ?
    C8 C9 H9 . . 119.6 ?
    C10 C9 H9 . . 119.6 ?
    C11 C10 C9 . . 119.6(3) ?
    C11 C10 H10 . . 120.2 ?
    C9 C10 H10 . . 120.2 ?
    C10 C11 C6 . . 120.7(3) ?
    C10 C11 H11 . . 119.7 ?
    C6 C11 H11 . . 119.7 ?
    O1 C12 C13 . . 110.9(2) ?
    O1 C12 H12A . . 109.5 ?
    C13 C12 H12A . . 109.5 ?
    O1 C12 H12B . . 109.5 ?
    C13 C12 H12B . . 109.5 ?
    H12A C12 H12B . . 108.1 ?
    C18 C13 C14 . . 118.4(3) ?
    C18 C13 C12 . . 121.3(3) ?
    C14 C13 C12 . . 120.3(3) ?
    C13 C14 C15 . . 121.1(3) ?
    C13 C14 H14 . . 119.4 ?
    C15 C14 H14 . . 119.4 ?
    C16 C15 C14 . . 120.2(4) ?
    C16 C15 H15 . . 119.9 ?
    C14 C15 H15 . . 119.9 ?
    C15 C16 C17 . . 119.5(4) ?
    C15 C16 H16 . . 120.3 ?
    C17 C16 H16 . . 120.3 ?
    C16 C17 C18 . . 120.3(3) ?
    C16 C17 H17 . . 119.8 ?
    C18 C17 H17 . . 119.8 ?
    C13 C18 C17 . . 120.5(3) ?
    C13 C18 H18 . . 119.7 ?
    C17 C18 H18 . . 119.7 ?
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_site_symmetry_1
    _geom_torsion_site_symmetry_2
    _geom_torsion_site_symmetry_3
    _geom_torsion_site_symmetry_4
    _geom_torsion
    _geom_torsion_publ_flag
    O3 S1 N3 C1 . . . . 55.5(2) ?
    O2 S1 N3 C1 . . . . -175.9(2) ?
    C6 S1 N3 C1 . . . . -60.2(2) ?
    C4 N1 C1 N3 . . . . -179.9(2) ?
    C4 N1 C1 C2 . . . . 0.7(3) ?
    S1 N3 C1 N1 . . . . -1.7(3) ?
    S1 N3 C1 C2 . . . . 177.73(18) ?
    C3 N2 C2 O1 . . . . -177.2(2) ?
    C3 N2 C2 C1 . . . . 1.1(4) ?
    C12 O1 C2 N2 . . . . -21.7(4) ?
    C12 O1 C2 C1 . . . . 159.9(2) ?
    N1 C1 C2 N2 . . . . -1.2(4) ?
    N3 C1 C2 N2 . . . . 179.3(2) ?
    N1 C1 C2 O1 . . . . 177.2(2) ?
    N3 C1 C2 O1 . . . . -2.3(3) ?
    C2 N2 C3 C4 . . . . -0.5(4) ?
    C2 N2 C3 C5 . . . . 178.2(2) ?
    C1 N1 C4 C3 . . . . -0.2(4) ?
    N2 C3 C4 N1 . . . . 0.1(4) ?
    C5 C3 C4 N1 . . . . -178.5(2) ?
    O3 S1 C6 C11 . . . . -2.3(2) ?
    O2 S1 C6 C11 . . . . -131.8(2) ?
    N3 S1 C6 C11 . . . . 115.3(2) ?
    O3 S1 C6 C7 . . . . 178.30(19) ?
    O2 S1 C6 C7 . . . . 48.8(2) ?
    N3 S1 C6 C7 . . . . -64.1(2) ?
    C11 C6 C7 C8 . . . . 0.3(4) ?
    S1 C6 C7 C8 . . . . 179.7(2) ?
    C11 C6 C7 Cl1 . . . . -177.00(19) ?
    S1 C6 C7 Cl1 . . . . 2.4(3) ?
    C6 C7 C8 C9 . . . . -0.2(4) ?
    Cl1 C7 C8 C9 . . . . 177.2(2) ?
    C7 C8 C9 C10 . . . . 0.5(4) ?
    C8 C9 C10 C11 . . . . -0.9(4) ?
    C9 C10 C11 C6 . . . . 1.1(4) ?
    C7 C6 C11 C10 . . . . -0.7(4) ?
    S1 C6 C11 C10 . . . . 179.8(2) ?
    C2 O1 C12 C13 . . . . -81.4(3) ?
    O1 C12 C13 C18 . . . . 138.0(3) ?
    O1 C12 C13 C14 . . . . -42.8(4) ?
    C18 C13 C14 C15 . . . . -0.4(5) ?
    C12 C13 C14 C15 . . . . -179.6(3) ?
    C13 C14 C15 C16 . . . . 0.6(6) ?
    C14 C15 C16 C17 . . . . -0.4(6) ?
    C15 C16 C17 C18 . . . . 0.0(6) ?
    C14 C13 C18 C17 . . . . 0.1(4) ?
    C12 C13 C18 C17 . . . . 179.3(3) ?
    C16 C17 C18 C13 . . . . 0.1(5) ?
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
    N3 H3 O2 3_756 0.86 2.26 3.061(3) 156 yes
    C11 H11 Cl1 4_666 0.93 2.66 3.488(3) 149 yes
