##############################################################################
###                                                                        ###
###        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 2.4.    #
#                                                                            #
# Software is freely available for graphical display of the structure(s) in  #
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data_I
_audit_creation_method     SHELXL-97
_chemical_name_systematic
;
(E)-3-(4-Hydroxy-3-methoxybenzylidene)-4-(4-hydroxyphenyl)pyrrolidin-
2-one
;
_chemical_name_common     ?
_chemical_formula_moiety     'C18 H17 N O4'
_chemical_formula_sum     'C18 H17 N O4'
_chemical_formula_iupac     'C18 H17 N O4'
_chemical_formula_weight     311.33
_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     6.3880(10)
_cell_length_b     14.520(2)
_cell_length_c     16.880(2)
_cell_angle_alpha     90.00
_cell_angle_beta     96.514(2)
_cell_angle_gamma     90.00
_cell_volume     1555.6(4)
_cell_formula_units_Z     4
_cell_measurement_reflns_used     1858
_cell_measurement_theta_min     2.429
_cell_measurement_theta_max     23.063
_cell_measurement_temperature     298(2)
_exptl_crystal_description     block
_exptl_crystal_colour     colourless
_exptl_crystal_size_max     0.47
_exptl_crystal_size_mid     0.42
_exptl_crystal_size_min     0.35
_exptl_crystal_density_diffrn     1.329
_exptl_crystal_density_meas     ?
_exptl_crystal_density_method     'not measured'
_exptl_crystal_F_000     656
_exptl_absorpt_coefficient_mu     0.094
_exptl_absorpt_correction_type     'multi-scan'
_exptl_absorpt_process_details     '(SADABS; Sheldrick, 1999)'
_exptl_absorpt_correction_T_min     0.9540
_exptl_absorpt_correction_T_max     0.969
_diffrn_ambient_temperature     298(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 CCD area-detector'
_diffrn_measurement_method     'φ and ω'
_diffrn_detector_area_resol_mean     10.0
_diffrn_reflns_number     9225
_diffrn_reflns_av_R_equivalents     0.0410
_diffrn_reflns_av_sigmaI/netI     0.0593
_diffrn_reflns_theta_min     1.86
_diffrn_reflns_theta_max     27.00
_diffrn_reflns_theta_full     27.00
_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     7
_diffrn_reflns_limit_k_min     -13
_diffrn_reflns_limit_k_max     18
_diffrn_reflns_limit_l_min     -20
_diffrn_reflns_limit_l_max     21
_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     3387
_reflns_number_gt     1756
_reflns_threshold_expression     I>2σ(I)
_refine_ls_structure_factor_coef     Fsqd
_refine_ls_matrix_type     full
_refine_ls_R_factor_all     0.1102
_refine_ls_R_factor_gt     0.0468
_refine_ls_wR_factor_gt     0.1028
_refine_ls_wR_factor_ref     0.1371
_refine_ls_goodness_of_fit_ref     1.020
_refine_ls_restrained_S_all     1.020
_refine_ls_number_reflns     3387
_refine_ls_number_parameters     209
_refine_ls_number_restraints     0
_refine_ls_hydrogen_treatment     constr
_refine_ls_weighting_scheme     calc
_refine_ls_weighting_details
          'calc w=1/[σ²(Fo²)+(0.0524P)²+0.295P] 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     ?
_refine_ls_shift/su_max_lt     0.000
_refine_ls_shift/su_mean     0.000
_refine_diff_density_max     0.218
_refine_diff_density_min     -0.202
_refine_ls_extinction_method     none
_refine_ls_extinction_coef     ?
_refine_ls_abs_structure_details     ?
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'
_computing_data_collection     'SMART (Bruker, 2001)'
_computing_cell_refinement     'SMART (Bruker, 2001)'
_computing_data_reduction     'SAINT (Bruker, 2001)'
_computing_structure_solution     'SHELXS97 (Sheldrick, 2008)'
_computing_structure_refinement     'SHELXL97 (Sheldrick, 2008)'
_computing_molecular_graphics     'SHELXTL (Sheldrick, 2008)'
_computing_publication_material     'SHELXTL (Sheldrick, 2008)'
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
    N N 0.1955(3) 0.50621(13) 0.43227(10) 0.0407(5) Uani d . 1 . .
    H H1 0.1694 0.5304 0.4766 0.049 Uiso calc R 1 . .
    O O1 -0.1146(2) 0.42888(11) 0.40852(9) 0.0482(4) Uani d . 1 . .
    O O2 0.3756(3) 0.78432(11) 0.09921(11) 0.0678(6) Uani d . 1 . .
    H H2 0.2621 0.8112 0.0921 0.102 Uiso calc R 1 . .
    O O3 0.5094(3) 0.35253(12) 0.04340(10) 0.0600(5) Uani d . 1 . .
    O O4 0.2796(3) 0.20997(13) -0.01836(11) 0.0762(6) Uani d . 1 . .
    H H4 0.3957 0.2277 -0.0283 0.114 Uiso calc R 1 . .
    C C1 0.0580(4) 0.45390(14) 0.38830(13) 0.0372(5) Uani d . 1 . .
    C C2 0.1463(3) 0.43166(15) 0.31329(12) 0.0358(5) Uani d . 1 . .
    C C3 0.3493(3) 0.48408(15) 0.31322(12) 0.0382(5) Uani d . 1 . .
    H H3 0.4610 0.4408 0.3031 0.046 Uiso calc R 1 . .
    C C4 0.3928(4) 0.5193(2) 0.39970(13) 0.0536(7) Uani d . 1 . .
    H H4A 0.5045 0.4840 0.4294 0.064 Uiso calc R 1 . .
    H H4B 0.4325 0.5838 0.4008 0.064 Uiso calc R 1 . .
    C C5 0.3457(3) 0.56253(15) 0.25340(12) 0.0365(5) Uani d . 1 . .
    C C6 0.1668(4) 0.59272(15) 0.20783(14) 0.0433(6) Uani d . 1 . .
    H H6 0.0395 0.5631 0.2121 0.052 Uiso calc R 1 . .
    C C7 0.1720(4) 0.66655(16) 0.15552(14) 0.0472(6) Uani d . 1 . .
    H H7 0.0495 0.6858 0.1250 0.057 Uiso calc R 1 . .
    C C8 0.3594(4) 0.71071(16) 0.14939(14) 0.0476(6) Uani d . 1 . .
    C C9 0.5397(4) 0.68061(18) 0.19335(17) 0.0562(7) Uani d . 1 . .
    H H9 0.6671 0.7098 0.1884 0.067 Uiso calc R 1 . .
    C C10 0.5334(4) 0.60767(17) 0.24462(15) 0.0523(7) Uani d . 1 . .
    H H10 0.6572 0.5880 0.2741 0.063 Uiso calc R 1 . .
    C C11 0.0515(4) 0.37125(15) 0.26114(13) 0.0401(6) Uani d . 1 . .
    H H11 -0.0771 0.3493 0.2741 0.048 Uiso calc R 1 . .
    C C12 0.1159(4) 0.33400(15) 0.18741(13) 0.0396(6) Uani d . 1 . .
    C C13 0.2897(4) 0.36572(15) 0.15170(13) 0.0419(6) Uani d . 1 . .
    H H13 0.3690 0.4145 0.1747 0.050 Uiso calc R 1 . .
    C C14 0.3449(4) 0.32596(16) 0.08338(13) 0.0431(6) Uani d . 1 . .
    C C15 0.2293(4) 0.25225(17) 0.04909(14) 0.0507(7) Uani d . 1 . .
    C C16 0.0567(4) 0.22166(18) 0.08261(15) 0.0619(8) Uani d . 1 . .
    H H16 -0.0229 0.1732 0.0591 0.074 Uiso calc R 1 . .
    C C17 -0.0002(4) 0.26206(17) 0.15097(14) 0.0536(7) Uani d . 1 . .
    H H17 -0.1182 0.2407 0.1729 0.064 Uiso calc R 1 . .
    C C18 0.6343(4) 0.4276(2) 0.07462(17) 0.0672(8) Uani d . 1 . .
    H H18A 0.5482 0.4818 0.0749 0.101 Uiso calc R 1 . .
    H H18B 0.7457 0.4382 0.0420 0.101 Uiso calc R 1 . .
    H H18C 0.6937 0.4137 0.1281 0.101 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
    N C1 . 1.323(3) ?
    N C4 . 1.444(3) ?
    N H1 . 0.8600 ?
    O1 C1 . 1.245(2) ?
    O2 C8 . 1.375(3) ?
    O2 H2 . 0.8200 ?
    O3 C14 . 1.367(3) ?
    O3 C18 . 1.417(3) ?
    O4 C15 . 1.364(3) ?
    O4 H4 . 0.8200 ?
    C1 C2 . 1.479(3) ?
    C2 C11 . 1.338(3) ?
    C2 C3 . 1.504(3) ?
    C3 C5 . 1.521(3) ?
    C3 C4 . 1.542(3) ?
    C3 H3 . 0.9800 ?
    C4 H4A . 0.9700 ?
    C4 H4B . 0.9700 ?
    C5 C6 . 1.375(3) ?
    C5 C10 . 1.389(3) ?
    C6 C7 . 1.392(3) ?
    C6 H6 . 0.9300 ?
    C7 C8 . 1.372(3) ?
    C7 H7 . 0.9300 ?
    C8 C9 . 1.369(3) ?
    C9 C10 . 1.371(3) ?
    C9 H9 . 0.9300 ?
    C10 H10 . 0.9300 ?
    C11 C12 . 1.458(3) ?
    C11 H11 . 0.9300 ?
    C12 C17 . 1.384(3) ?
    C12 C13 . 1.400(3) ?
    C13 C14 . 1.371(3) ?
    C13 H13 . 0.9300 ?
    C14 C15 . 1.389(3) ?
    C15 C16 . 1.369(3) ?
    C16 C17 . 1.379(3) ?
    C16 H16 . 0.9300 ?
    C17 H17 . 0.9300 ?
    C18 H18A . 0.9600 ?
    C18 H18B . 0.9600 ?
    C18 H18C . 0.9600 ?
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
    C1 N C4 . . 114.5(2) ?
    C1 N H1 . . 122.8 ?
    C4 N H1 . . 122.8 ?
    C8 O2 H2 . . 109.5 ?
    C14 O3 C18 . . 117.7(2) ?
    C15 O4 H4 . . 109.5 ?
    O1 C1 N . . 124.4(2) ?
    O1 C1 C2 . . 127.4(2) ?
    N C1 C2 . . 108.20(19) ?
    C11 C2 C1 . . 121.2(2) ?
    C11 C2 C3 . . 131.1(2) ?
    C1 C2 C3 . . 107.6(2) ?
    C2 C3 C5 . . 115.6(2) ?
    C2 C3 C4 . . 103.3(2) ?
    C5 C3 C4 . . 111.6(2) ?
    C2 C3 H3 . . 108.7 ?
    C5 C3 H3 . . 108.7 ?
    C4 C3 H3 . . 108.7 ?
    N C4 C3 . . 104.2(2) ?
    N C4 H4A . . 110.9 ?
    C3 C4 H4A . . 110.9 ?
    N C4 H4B . . 110.9 ?
    C3 C4 H4B . . 110.9 ?
    H4A C4 H4B . . 108.9 ?
    C6 C5 C10 . . 117.5(2) ?
    C6 C5 C3 . . 124.0(2) ?
    C10 C5 C3 . . 118.4(2) ?
    C5 C6 C7 . . 121.5(2) ?
    C5 C6 H6 . . 119.2 ?
    C7 C6 H6 . . 119.2 ?
    C8 C7 C6 . . 119.4(2) ?
    C8 C7 H7 . . 120.3 ?
    C6 C7 H7 . . 120.3 ?
    C9 C8 C7 . . 119.8(2) ?
    C9 C8 O2 . . 117.7(2) ?
    C7 C8 O2 . . 122.5(2) ?
    C8 C9 C10 . . 120.4(2) ?
    C8 C9 H9 . . 119.8 ?
    C10 C9 H9 . . 119.8 ?
    C9 C10 C5 . . 121.3(2) ?
    C9 C10 H10 . . 119.4 ?
    C5 C10 H10 . . 119.4 ?
    C2 C11 C12 . . 130.9(2) ?
    C2 C11 H11 . . 114.6 ?
    C12 C11 H11 . . 114.6 ?
    C17 C12 C13 . . 117.9(2) ?
    C17 C12 C11 . . 118.1(2) ?
    C13 C12 C11 . . 124.0(2) ?
    C14 C13 C12 . . 121.0(2) ?
    C14 C13 H13 . . 119.5 ?
    C12 C13 H13 . . 119.5 ?
    O3 C14 C13 . . 125.6(2) ?
    O3 C14 C15 . . 114.4(2) ?
    C13 C14 C15 . . 120.0(2) ?
    O4 C15 C16 . . 118.4(2) ?
    O4 C15 C14 . . 122.0(2) ?
    C16 C15 C14 . . 119.5(2) ?
    C15 C16 C17 . . 120.6(2) ?
    C15 C16 H16 . . 119.7 ?
    C17 C16 H16 . . 119.7 ?
    C16 C17 C12 . . 120.9(2) ?
    C16 C17 H17 . . 119.5 ?
    C12 C17 H17 . . 119.5 ?
    O3 C18 H18A . . 109.5 ?
    O3 C18 H18B . . 109.5 ?
    H18A C18 H18B . . 109.5 ?
    O3 C18 H18C . . 109.5 ?
    H18A C18 H18C . . 109.5 ?
    H18B C18 H18C . . 109.5 ?
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
    C4 N C1 O1 . . . . 174.6(2) ?
    C4 N C1 C2 . . . . -5.3(3) ?
    O1 C1 C2 C11 . . . . -7.4(4) ?
    N C1 C2 C11 . . . . 172.5(2) ?
    O1 C1 C2 C3 . . . . 175.2(2) ?
    N C1 C2 C3 . . . . -4.9(2) ?
    C11 C2 C3 C5 . . . . 72.8(3) ?
    C1 C2 C3 C5 . . . . -110.1(2) ?
    C11 C2 C3 C4 . . . . -165.1(2) ?
    C1 C2 C3 C4 . . . . 12.0(2) ?
    C1 N C4 C3 . . . . 12.9(3) ?
    C2 C3 C4 N . . . . -14.5(2) ?
    C5 C3 C4 N . . . . 110.3(2) ?
    C2 C3 C5 C6 . . . . 7.3(3) ?
    C4 C3 C5 C6 . . . . -110.3(2) ?
    C2 C3 C5 C10 . . . . -173.59(19) ?
    C4 C3 C5 C10 . . . . 68.8(2) ?
    C10 C5 C6 C7 . . . . -0.9(3) ?
    C3 C5 C6 C7 . . . . 178.2(2) ?
    C5 C6 C7 C8 . . . . -0.3(3) ?
    C6 C7 C8 C9 . . . . 1.4(4) ?
    C6 C7 C8 O2 . . . . -179.7(2) ?
    C7 C8 C9 C10 . . . . -1.2(4) ?
    O2 C8 C9 C10 . . . . 179.8(2) ?
    C8 C9 C10 C5 . . . . 0.0(4) ?
    C6 C5 C10 C9 . . . . 1.0(3) ?
    C3 C5 C10 C9 . . . . -178.1(2) ?
    C1 C2 C11 C12 . . . . -175.0(2) ?
    C3 C2 C11 C12 . . . . 1.8(4) ?
    C2 C11 C12 C17 . . . . 170.9(2) ?
    C2 C11 C12 C13 . . . . -8.2(4) ?
    C17 C12 C13 C14 . . . . -0.9(4) ?
    C11 C12 C13 C14 . . . . 178.3(2) ?
    C18 O3 C14 C13 . . . . -0.1(4) ?
    C18 O3 C14 C15 . . . . 179.8(2) ?
    C12 C13 C14 O3 . . . . 179.0(2) ?
    C12 C13 C14 C15 . . . . -0.8(4) ?
    O3 C14 C15 O4 . . . . 0.8(4) ?
    C13 C14 C15 O4 . . . . -179.3(2) ?
    O3 C14 C15 C16 . . . . -177.9(2) ?
    C13 C14 C15 C16 . . . . 2.0(4) ?
    O4 C15 C16 C17 . . . . 179.8(2) ?
    C14 C15 C16 C17 . . . . -1.5(4) ?
    C15 C16 C17 C12 . . . . -0.3(4) ?
    C13 C12 C17 C16 . . . . 1.4(4) ?
    C11 C12 C17 C16 . . . . -177.8(2) ?
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
    N H1 O1 3_566 0.86 2.09 2.948(2) 172.0
    O2 H2 O1 2 0.82 1.95 2.675(2) 146.7
    O4 H4 O2 3_665 0.82 2.00 2.721(2) 146.5
data_global
_journal_date_recd_electronic     2008-02-28
_journal_date_accepted     2008-03-31
_journal_name_full     'Acta Crystallographica, Section E'
_journal_year     2008
_journal_volume     64
_journal_issue      5
_journal_page_first     o814
_journal_page_last     o814
_journal_paper_category     QO
_journal_coeditor_code     LX2053
_publ_contact_author_name     'Bo-Yang Yu'
_publ_contact_author_address
;
Department of Complex Prescription of TCM,
China Pharmaceutical University,
Nanjing 210038, People's Republic of China
;
_publ_contact_author_email     'boyangyu59@163.com'
_publ_contact_author_fax     '+86-25-83313080'
_publ_contact_author_phone     '+86-25-85391042'
_publ_section_title
;\
(E)-3-(4-Hydroxy-3-methoxybenzylidene)-4-(4-hydroxyphenyl)pyrrolidin-2-\
one
;
loop_
    _publ_author_name
    _publ_author_footnote
    _publ_author_address
    'Zhou, Yi-Feng' .
;
Department of Complex Prescription of TCM,
China Pharmaceutical University,
Nanjing 210038, People's Republic of China
;
    'Wang, Xiao-Bing' .
;
Department of Natural Medicinal Chemistry
China Pharmaceutical University
Nanjing, 210009
People's Republic of China
;
    'Qi, Jin' .
;
Department of Complex Prescription of TCM,
China Pharmaceutical University,
Nanjing 210038, People's Republic of China
;
    'Yu, Bo-Yang' .
;
Department of Complex Prescription of TCM,
China Pharmaceutical University,
Nanjing 210038, People's Republic of China
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_exptl_special_details
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Spectroscopic analysis: ESI-MS: m/z 310 [M---H]⁻; ¹HNMR
(DMSO-d₆, 400
MHz, δ, p.p.m.): 4.51(1H, d, J = 7.34 Hz, H-3), 2.99
(1H, d, J = 9.46 Hz, H-4a), 3.77 (1H, t, J = 8.85
Hz, H-4 b), 7.02 (2H, d, J = 8.14 Hz, H-6,10), 6.67(3H,
d, J = 8.15 Hz, H-7, 9, 17), 6.86(2H, d, J=7.37 Hz, H-11,
16),7.22 (1H, s, H-13), 3.51(3H, s, H-OCH₃), 7.90 (1H,
s, H---NH); ¹³C NMR (DMSO-d₆,400 MHz, δ, p.p.m.): 171.6(C1), 131.7(C2),
42.0(C3), 49.6(C4), 131.1(C5), 128.2(C6), 116.0(C7),156.4(C8), 116.0
(C9), 128.2(C10), 134.2(C11), 126.5(C12), 113.5(C13), 147.9(C14), 147.8
(C15), 115.8(C16), 124.9(C17), 55.7(C18).
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