##############################################################################
###                                                                        ###
###        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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#                                                                            #
#            Copyright International Union of Crystallography                #
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##############################################################################
                                             
data_global
_audit_creation_method     'from SHELXL97 CIF and IUCr SHELXL97-template'
_journal_date_recd_electronic     2003-04-14
_journal_date_accepted     2003-05-06
_journal_name_full     'Acta Crystallographica, Section E'
_journal_year     2003
_journal_volume     59
_journal_issue      6
_journal_page_first     o814
_journal_page_last     o816
_journal_paper_category     EO
_publ_contact_author_name     'Prof. Ma, Yong-Xiang'
_publ_contact_author_address
;
National Laboratory of Applied Organic Chemistry,
Lanzhou University,
Lanzhou 730000,
P. R. China
;
_publ_contact_author_email     llyyjz@nju.edu.cn
_publ_contact_author_fax     ?
_publ_contact_author_phone     ?
_publ_section_title
;
3-[(5-Chloro-2-hydroxyphenyl)phenylmethyl]-2-(2-pyridyl)-1H-benzimidazole
;
loop_
    _publ_author_name
    _publ_author_address
    'Jian, Pan-Ming'
;
National Laboratory of Applied Organic Chemistry,
Lanzhou University,
Lanzhou 730000,
People's Republic of China
;
    'Li, Yi-Zhi'
;
Coordination Chemistry Institute,
State Key Laboratory of Coordination Chemistry
Nanjing University,
Nanjing 210093
People's Republic of China
;
    'Wu, Xiao-Li'
;
National Laboratory of Applied Organic Chemistry,
Lanzhou University,
Lanzhou 730000,
People's Republic of China
;
    'Ma, Yong-Xiang'
;
National Laboratory of Applied Organic Chemistry,
Lanzhou University,
Lanzhou 730000,
People's Republic of China
;
    'Pan, Da-Hua'
;
National Laboratory of Applied Organic Chemistry,
Lanzhou University,
Lanzhou 730000,
People's Republic of China
;
    'Chen, Bao-Hua'
;
National Laboratory of Applied Organic Chemistry,
Lanzhou University,
Lanzhou 730000,
People's Republic of China
;
data_II
_chemical_name_systematic
;
3-[(5-Chloro-2-hydroxyphenyl)phenylmethyl]-2-(2-pyridyl)-1H-benzimidazole
;
_chemical_name_common     ?
_chemical_formula_moiety     'C25 H18 Cl N3 O'
_chemical_formula_sum     'C25 H18 Cl N3 O'
_chemical_formula_iupac     'C25 H18 Cl N3 O'
_chemical_formula_weight     411.87
_chemical_melting_point     ?
_symmetry_cell_setting     monoclinic
_symmetry_space_group_name_H-M     'P 21/c'
_symmetry_space_group_name_Hall     '-P 2ybc'
loop_
    _symmetry_equiv_pos_as_xyz
    'x, y, z'
    '-x, y+1/2, -z+1/2'
    '-x, -y, -z'
    'x, -y-1/2, z-1/2'
_cell_length_a     13.515(2)
_cell_length_b     9.597(2)
_cell_length_c     16.875(2)
_cell_angle_alpha     90.00
_cell_angle_beta     110.010(10)
_cell_angle_gamma     90.00
_cell_volume     2056.6(6)
_cell_formula_units_Z     4
_cell_measurement_reflns_used     25
_cell_measurement_theta_min     2.12
_cell_measurement_theta_max     23.22
_cell_measurement_temperature     293(2)
_exptl_crystal_description     block
_exptl_crystal_colour     Colorless
_exptl_crystal_size_max     0.3
_exptl_crystal_size_mid     0.2
_exptl_crystal_size_min     0.2
_exptl_crystal_density_diffrn     1.330
_exptl_crystal_density_meas     ?
_exptl_crystal_density_method     'not measured'
_exptl_crystal_F_000     856
_exptl_absorpt_coefficient_mu     0.208
_exptl_absorpt_correction_type     '\y scan'
_exptl_absorpt_process_details     '(XPREP; Bruker, 2000)'
_exptl_absorpt_correction_T_min     0.95
_exptl_absorpt_correction_T_max     0.96
_exptl_special_details
;
;
_diffrn_ambient_temperature     293(2)
_diffrn_radiation_type     'MoK\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_source     'sealed tube'
_diffrn_radiation_monochromator     'graphite'
_diffrn_measurement_device_type     'Bruker P4'
_diffrn_measurement_method     ω
_diffrn_detector_area_resol_mean     ?
_diffrn_reflns_number     10228
_diffrn_reflns_av_R_equivalents     0.0450
_diffrn_reflns_av_sigmaI/netI     0.0480
_diffrn_reflns_theta_min     1.60
_diffrn_reflns_theta_max     25.99
_diffrn_reflns_theta_full     25.99
_diffrn_measured_fraction_theta_max     0.985
_diffrn_measured_fraction_theta_full     0.985
_diffrn_reflns_limit_h_min     -16
_diffrn_reflns_limit_h_max     16
_diffrn_reflns_limit_k_min     -11
_diffrn_reflns_limit_k_max     11
_diffrn_reflns_limit_l_min     -19
_diffrn_reflns_limit_l_max     19
_diffrn_standards_number     3
_diffrn_standards_interval_count     97
_diffrn_standards_interval_time     ?
_diffrn_standards_decay_%     0.005
_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     3982
_reflns_number_gt     3129
_reflns_threshold_expression     I>2σ(I)
_refine_ls_structure_factor_coef     Fsqd
_refine_ls_matrix_type     full
_refine_ls_R_factor_all     0.0404
_refine_ls_R_factor_gt     0.0335
_refine_ls_wR_factor_gt     0.0891
_refine_ls_wR_factor_ref     0.0923
_refine_ls_goodness_of_fit_ref     1.005
_refine_ls_restrained_S_all     1.005
_refine_ls_number_reflns     3982
_refine_ls_number_parameters     343
_refine_ls_number_restraints     0
_refine_ls_hydrogen_treatment     refall
_refine_ls_weighting_scheme     calc
_refine_ls_weighting_details
               'calc w = 1/[σ²(Fo²)+(0.02P)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     <0.001
_refine_ls_shift/su_mean     0.000
_refine_diff_density_max     0.203
_refine_diff_density_min     -0.149
_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'
    'Cl' 'Cl' 0.1484 0.1585
                         'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
_computing_data_collection     'XSCANS  (Bruker, 2000)'
_computing_cell_refinement     'XSCANS'
_computing_data_reduction     'XSCANS'
_computing_structure_solution     'SHELXTL (Bruker, 2000)'
_computing_structure_refinement     'SHELXTL'
_computing_molecular_graphics     'SHELXTL'
_computing_publication_material     'SHELXTL'
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
    N2 0.27370(8) 0.13167(11) 0.18508(6) 0.0471(3) Uani d . 1 . . N
    N1 0.39468(9) -0.02686(12) 0.18339(7) 0.0547(3) Uani d . 1 . . N
    C6 0.28406(11) 0.14024(14) 0.10580(8) 0.0493(3) Uani d . 1 . . C
    C7 0.34144(11) 0.02950(14) 0.22825(8) 0.0504(3) Uani d . 1 . . C
    C1 0.35919(11) 0.04011(15) 0.10617(9) 0.0534(3) Uani d . 1 . . C
    C8 0.35184(12) -0.02258(15) 0.31334(9) 0.0567(4) Uani d . 1 . . C
    C14 0.09869(11) 0.18864(14) 0.19490(8) 0.0518(3) Uani d . 1 . . C
    C20 0.23141(11) 0.37906(13) 0.19685(8) 0.0490(3) Uani d . 1 . . C
    C13 0.21320(11) 0.22933(13) 0.21886(9) 0.0473(3) Uani d . 1 . . C
    C21 0.15082(13) 0.46110(15) 0.14484(9) 0.0559(4) Uani d . 1 . . C
    N3 0.26999(11) -0.00367(14) 0.33936(8) 0.0674(4) Uani d . 1 . . N
    C5 0.23442(13) 0.22136(16) 0.03491(9) 0.0578(4) Uani d . 1 . . C
    C25 0.33245(11) 0.43563(15) 0.23018(9) 0.0536(3) Uani d . 1 . . C
    C15 0.05079(12) 0.08976(17) 0.13415(9) 0.0604(4) Uani d . 1 . . C
    C23 0.26988(14) 0.65271(18) 0.15976(10) 0.0671(4) Uani d . 1 . . C
    C2 0.38656(13) 0.01773(17) 0.03450(10) 0.0613(4) Uani d . 1 . . C
    C22 0.17066(13) 0.59602(16) 0.12594(9) 0.0621(4) Uani d . 1 . . C
    C3 0.33773(13) 0.09732(18) -0.03571(10) 0.0652(4) Uani d . 1 . . C
    C19 0.03843(12) 0.25473(18) 0.23605(10) 0.0640(4) Uani d . 1 . . C
    C4 0.26306(14) 0.19749(17) -0.03527(10) 0.0637(4) Uani d . 1 . . C
    C24 0.35072(14) 0.57270(17) 0.21221(11) 0.0649(4) Uani d . 1 . . C
    C18 -0.06732(13) 0.2243(2) 0.21586(12) 0.0741(5) Uani d . 1 . . C
    C16 -0.05565(14) 0.0605(2) 0.11388(12) 0.0749(5) Uani d . 1 . . C
    C10 0.4456(2) -0.1491(2) 0.43792(13) 0.0946(6) Uani d . 1 . . C
    C9 0.44085(16) -0.0947(2) 0.36024(12) 0.0807(5) Uani d . 1 . . C
    C17 -0.11394(15) 0.1269(2) 0.15494(12) 0.0777(5) Uani d . 1 . . C
    C12 0.27714(17) -0.0583(2) 0.41450(11) 0.0792(5) Uani d . 1 . . C
    C11 0.36287(19) -0.1305(2) 0.46453(13) 0.0883(6) Uani d . 1 . . C
    Cl1 0.06903(5) 0.69575(5) 0.05804(3) 0.0996(2) Uani d . 1 . . Cl
    O1 0.41034(8) 0.35159(11) 0.28005(6) 0.0625(3) Uani d . 1 . . O
    H13 0.2429(10) 0.2156(13) 0.2782(8) 0.047(3) Uiso d . 1 . . H
    H5 0.1811(12) 0.2929(16) 0.0350(9) 0.065(4) Uiso d . 1 . . H
    H21 0.0784(13) 0.4275(16) 0.1212(9) 0.068(4) Uiso d . 1 . . H
    H15 0.0938(13) 0.0354(16) 0.1066(9) 0.067(4) Uiso d . 1 . . H
    H19 0.0747(13) 0.3327(17) 0.2798(10) 0.075(5) Uiso d . 1 . . H
    H23 0.2850(14) 0.749(2) 0.1481(11) 0.090(6) Uiso d . 1 . . H
    H24 0.4235(14) 0.6024(18) 0.2399(10) 0.085(5) Uiso d . 1 . . H
    H2 0.4402(14) -0.0545(18) 0.0399(10) 0.082(5) Uiso d . 1 . . H
    H4 0.2233(13) 0.2518(17) -0.0894(10) 0.079(5) Uiso d . 1 . . H
    H3 0.3580(12) 0.0765(16) -0.0898(10) 0.071(4) Uiso d . 1 . . H
    H16 -0.0850(16) -0.008(2) 0.0682(11) 0.096(6) Uiso d . 1 . . H
    H17 -0.1927(18) 0.110(2) 0.1410(13) 0.119(7) Uiso d . 1 . . H
    H12 0.2131(16) -0.044(2) 0.4339(11) 0.102(6) Uiso d . 1 . . H
    H11 0.3677(18) -0.169(2) 0.5182(14) 0.125(8) Uiso d . 1 . . H
    H18 -0.1087(19) 0.271(2) 0.2452(14) 0.126(8) Uiso d . 1 . . H
    H9 0.4990(17) -0.091(2) 0.3391(12) 0.108(7) Uiso d . 1 . . H
    H10 0.516(2) -0.191(3) 0.4730(17) 0.171(11) Uiso d . 1 . . H
    H1' 0.4802(18) 0.397(2) 0.2964(12) 0.114(7) Uiso d . 1 . . H
_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.
Least-squares planes (x,y,z in crystal coordinates) and deviations from them
 (* indicates atom used to define plane)
  3.8274 (0.0129) x + 7.9081 (0.0035) y + 6.1455 (0.0090) z = 3.1747 (0.0027)
 *   -0.0810 (0.0013)  C8
 *   -0.0222 (0.0016)  C9
 *    0.0426 (0.0017)  C10
 *    0.0368 (0.0017)  C11
 *   -0.0277 (0.0012)  C12
 *    0.0515 (0.0007)  N2
 Rms deviation of fitted atoms =   0.0477
  8.7556 (0.0051) x + 6.5746 (0.0035) y + 1.5415 (0.0053) z = 3.5549 (0.0013)
 Angle to previous plane (with approximate esd) = 24.29 ( 0.08 )
 *    0.0174 (0.0013)  C1
 *   -0.0006 (0.0012)  C2
 *   -0.0131 (0.0012)  C3
 *   -0.0076 (0.0012)  C4
 *    0.0068 (0.0011)  C5
 *    0.0174 (0.0012)  C6
 *   -0.0196 (0.0010)  C7
 *    0.0068 (0.0010)  N1
 *   -0.0075 (0.0010)  N2
 Rms deviation of fitted atoms =0.0123
;
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
    N2 C7 . 1.3688(17) ?
    N2 C6 . 1.3945(16) ?
    N2 C13 . 1.4802(16) y
    N1 C7 . 1.3252(17) ?
    N1 C1 . 1.3833(17) ?
    C6 C5 . 1.392(2) ?
    C6 C1 . 1.3965(19) ?
    C7 C8 . 1.4810(19) ?
    C1 C2 . 1.397(2) ?
    C8 N3 . 1.3348(19) ?
    C8 C9 . 1.379(2) ?
    C14 C15 . 1.384(2) ?
    C14 C19 . 1.3909(19) ?
    C14 C13 . 1.5109(19) y
    C20 C21 . 1.3865(19) ?
    C20 C25 . 1.3965(19) ?
    C20 C13 . 1.5251(18) y
    C13 H13 . 0.952(13) y
    C21 C22 . 1.382(2) ?
    C21 H21 . 0.976(16) ?
    N3 C12 . 1.345(2) ?
    C5 C4 . 1.385(2) ?
    C5 H5 . 0.996(15) ?
    C25 O1 . 1.3640(17) ?
    C25 C24 . 1.391(2) ?
    C15 C16 . 1.389(2) ?
    C15 H15 . 1.005(15) ?
    C23 C22 . 1.377(2) ?
    C23 C24 . 1.380(2) ?
    C23 H23 . 0.977(19) ?
    C2 C3 . 1.374(2) ?
    C2 H2 . 0.984(17) ?
    C22 Cl1 . 1.7431(16) ?
    C3 C4 . 1.396(2) ?
    C3 H3 . 1.058(15) ?
    C19 C18 . 1.382(2) ?
    C19 H19 . 1.047(16) ?
    C4 H4 . 1.029(17) ?
    C24 H24 . 0.975(18) ?
    C18 C17 . 1.373(3) ?
    C18 H18 . 0.97(2) ?
    C16 C17 . 1.371(3) ?
    C16 H16 . 0.988(18) ?
    C10 C11 . 1.352(3) ?
    C10 C9 . 1.392(3) ?
    C10 H10 . 1.01(3) ?
    C9 H9 . 0.97(2) ?
    C17 H17 . 1.02(2) ?
    C12 C11 . 1.366(3) ?
    C12 H12 . 1.03(2) ?
    C11 H11 . 0.96(2) ?
    O1 H1' . 0.99(2) ?
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
    C7 N2 C6 . . 106.53(10) ?
    C7 N2 C13 . . 127.27(11) ?
    C6 N2 C13 . . 125.60(11) ?
    C7 N1 C1 . . 105.52(11) ?
    C5 C6 N2 . . 132.88(13) ?
    C5 C6 C1 . . 121.64(12) ?
    N2 C6 C1 . . 105.46(12) ?
    N1 C7 N2 . . 112.54(12) ?
    N1 C7 C8 . . 121.75(12) ?
    N2 C7 C8 . . 125.59(12) ?
    N1 C1 C6 . . 109.95(11) ?
    N1 C1 C2 . . 129.42(14) ?
    C6 C1 C2 . . 120.62(14) ?
    N3 C8 C9 . . 122.55(14) ?
    N3 C8 C7 . . 117.30(13) ?
    C9 C8 C7 . . 120.04(14) ?
    C15 C14 C19 . . 118.49(14) ?
    C15 C14 C13 . . 123.49(12) ?
    C19 C14 C13 . . 118.01(12) ?
    C21 C20 C25 . . 118.84(13) ?
    C21 C20 C13 . . 122.13(12) ?
    C25 C20 C13 . . 119.03(12) ?
    N2 C13 C14 . . 112.56(11) y
    N2 C13 C20 . . 110.27(10) y
    C14 C13 C20 . . 114.47(11) y
    N2 C13 H13 . . 103.2(8) y
    C14 C13 H13 . . 105.7(8) y
    C20 C13 H13 . . 110.0(8) y
    C22 C21 C20 . . 120.39(15) ?
    C22 C21 H21 . . 117.5(9) ?
    C20 C21 H21 . . 122.1(9) ?
    C8 N3 C12 . . 117.19(15) ?
    C4 C5 C6 . . 116.67(15) ?
    C4 C5 H5 . . 122.0(8) ?
    C6 C5 H5 . . 121.3(8) ?
    O1 C25 C24 . . 122.46(14) ?
    O1 C25 C20 . . 117.42(13) ?
    C24 C25 C20 . . 120.13(14) ?
    C14 C15 C16 . . 120.23(16) ?
    C14 C15 H15 . . 120.0(9) ?
    C16 C15 H15 . . 119.7(9) ?
    C22 C23 C24 . . 119.40(16) ?
    C22 C23 H23 . . 122.0(11) ?
    C24 C23 H23 . . 118.6(11) ?
    C3 C2 C1 . . 118.02(15) ?
    C3 C2 H2 . . 126.4(9) ?
    C1 C2 H2 . . 115.6(9) ?
    C23 C22 C21 . . 120.87(15) ?
    C23 C22 Cl1 . . 119.47(12) ?
    C21 C22 Cl1 . . 119.66(13) ?
    C2 C3 C4 . . 120.87(15) ?
    C2 C3 H3 . . 116.7(8) ?
    C4 C3 H3 . . 122.4(8) ?
    C18 C19 C14 . . 120.87(16) ?
    C18 C19 H19 . . 121.3(9) ?
    C14 C19 H19 . . 117.7(9) ?
    C5 C4 C3 . . 122.18(16) ?
    C5 C4 H4 . . 117.5(9) ?
    C3 C4 H4 . . 120.2(9) ?
    C23 C24 C25 . . 120.35(16) ?
    C23 C24 H24 . . 126.3(11) ?
    C25 C24 H24 . . 113.4(11) ?
    C17 C18 C19 . . 119.97(18) ?
    C17 C18 H18 . . 120.0(14) ?
    C19 C18 H18 . . 120.0(14) ?
    C17 C16 C15 . . 120.49(18) ?
    C17 C16 H16 . . 123.9(11) ?
    C15 C16 H16 . . 115.6(12) ?
    C11 C10 C9 . . 119.1(2) ?
    C11 C10 H10 . . 124.9(16) ?
    C9 C10 H10 . . 115.6(16) ?
    C8 C9 C10 . . 118.63(19) ?
    C8 C9 H9 . . 115.3(12) ?
    C10 C9 H9 . . 125.5(12) ?
    C16 C17 C18 . . 119.93(17) ?
    C16 C17 H17 . . 123.0(12) ?
    C18 C17 H17 . . 117.0(12) ?
    N3 C12 C11 . . 123.55(19) ?
    N3 C12 H12 . . 116.6(11) ?
    C11 C12 H12 . . 119.8(11) ?
    C10 C11 C12 . . 119.00(19) ?
    C10 C11 H11 . . 117.7(14) ?
    C12 C11 H11 . . 123.3(14) ?
    C25 O1 H1' . . 112.0(12) ?
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
    O1 H1' N1 2_655 0.99(2) 1.77(2) 2.7520(16) 174.8(17)
    C13 H13 N3 . 0.952(13) 2.317(13) 2.9422(19) 122.6(9)
    C15 H15 N2 . 1.005(15) 2.513(15) 2.8643(19) 100.0(10)
    C23 H23 N1 1_565 0.977(19) 2.568(19) 3.464(2) 152.5(14)
