##############################################################################
###                                                                        ###
###        Electronic paper (Acta Crystallographica Section E)             ###
###                                                                        ###
##############################################################################
#                                                                            #
# 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/  #
# cif/home.html                                                              #
#                                                                            #
#            Copyright International Union of Crystallography                #
#                                                                            #
##############################################################################
                                             
data_global
_audit_creation_method     SHELXL-97
_journal_date_recd_electronic     2005-03-22
_journal_date_accepted     2005-06-17
_journal_name_full     'Acta Crystallographica, Section E'
_journal_year     2005
_journal_volume     61
_journal_issue      7
_journal_page_first     o2261
_journal_page_last     o2262
_journal_paper_category     EO
_publ_contact_author_name     'Prof. Guang-Fu Yang'
_publ_contact_author_address
; Key Laboratory of Pesticide and Chemical Biology of Ministry of Education
   College of Chemistry
   Central China Normal University
   Wuhan  430079
   China
;
_publ_contact_author_email     gfyang@mail.ccnu.edu.cn
_publ_contact_author_fax     '86 27 67867706'
_publ_contact_author_phone     '86 27 67867141'
_publ_section_title
;\
3-[3-(4-Chlorophenyl)-4-oxothiazolidin-2-yl]-6-methyl-4H-benzopyran-4-\
one
;
loop_
    _publ_author_name
    _publ_author_footnote
    _publ_author_address
    'Zhou, Zhong-Zhen' .
;
Key Laboratory of Pesticide and Chemical Biology of Ministry of Education
College of Chemistry
Central China Normal University
Wuhan 430079
People's Republic of China
;
    'Huang, Wei' .
;
Key Laboratory of Pesticide and Chemical Biology of Ministry of Education
College of Chemistry
Central China Normal University
Wuhan 430079
People's Republic of China
;
    'Zhao, Pei-Liang' .
;
Key Laboratory of Pesticide and Chemical Biology of Ministry of Education
College of Chemistry
Central China Normal University
Wuhan 430079
People's Republic of China
;
    'Chen, Qiong' .
;
Key Laboratory of Pesticide and Chemical Biology of Ministry of Education
College of Chemistry
Central China Normal University
Wuhan 430079
People's Republic of China
;
    'Yang, Guang-Fu' .
;
Key Laboratory of Pesticide and Chemical Biology of Ministry of Education
College of Chemistry
Central China Normal University
Wuhan 430079
People's Republic of China
;
data_I
_audit_creation_method     SHELXL-97
_chemical_name_systematic
;
3-[3-(4-Chlorophenyl)-4-oxothiazolidin-2-yl]-6-methyl-4H-benzopyran-4-one
;
_chemical_name_common     ?
_chemical_formula_moiety     'C19 H14 Cl N O3 S'
_chemical_formula_sum     'C19 H14 Cl N O3 S'
_chemical_formula_iupac     'C19 H14 Cl N O3 S'
_chemical_formula_weight     371.82
_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     11.1830(9)
_cell_length_b     13.9851(10)
_cell_length_c     12.3419(9)
_cell_angle_alpha     90.00
_cell_angle_beta     116.4450(10)
_cell_angle_gamma     90.00
_cell_volume     1728.2(2)
_cell_formula_units_Z     4
_cell_measurement_reflns_used     3801
_cell_measurement_theta_min     2.35
_cell_measurement_theta_max     27.70
_cell_measurement_temperature     293(2)
_exptl_crystal_description     block
_exptl_crystal_colour     colorless
_exptl_crystal_size_max     0.40
_exptl_crystal_size_mid     0.38
_exptl_crystal_size_min     0.34
_exptl_crystal_density_diffrn     1.429
_exptl_crystal_density_meas     ?
_exptl_crystal_density_method     'not measured'
_exptl_crystal_F_000     768
_exptl_absorpt_coefficient_mu     0.360
_exptl_absorpt_correction_type     'multi-scan'
_exptl_absorpt_process_details     '(SADABS; Sheldrick, 1997)'
_exptl_absorpt_correction_T_min     0.8695
_exptl_absorpt_correction_T_max     0.8875
_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 CCD area-detector'
_diffrn_measurement_method     'φ and ω'
_diffrn_detector_area_resol_mean     ?
_diffrn_reflns_number     9946
_diffrn_reflns_av_R_equivalents     0.0181
_diffrn_reflns_av_sigmaI/netI     0.0221
_diffrn_reflns_theta_min     2.05
_diffrn_reflns_theta_max     26.99
_diffrn_reflns_theta_full     26.99
_diffrn_measured_fraction_theta_max     0.995
_diffrn_measured_fraction_theta_full     0.995
_diffrn_reflns_limit_h_min     -13
_diffrn_reflns_limit_h_max     14
_diffrn_reflns_limit_k_min     -17
_diffrn_reflns_limit_k_max     13
_diffrn_reflns_limit_l_min     -14
_diffrn_reflns_limit_l_max     15
_diffrn_standards_number     0
_diffrn_standards_interval_count     0
_diffrn_standards_interval_time     0
_diffrn_standards_decay_%     0
_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     3747
_reflns_number_gt     2974
_reflns_threshold_expression     I>2σ(I)
_refine_ls_structure_factor_coef     Fsqd
_refine_ls_matrix_type     full
_refine_ls_R_factor_all     0.0551
_refine_ls_R_factor_gt     0.0443
_refine_ls_wR_factor_gt     0.1252
_refine_ls_wR_factor_ref     0.1344
_refine_ls_goodness_of_fit_ref     1.047
_refine_ls_restrained_S_all     1.047
_refine_ls_number_reflns     3747
_refine_ls_number_parameters     227
_refine_ls_number_restraints     0
_refine_ls_hydrogen_treatment     constr
_refine_ls_weighting_scheme     calc
_refine_ls_weighting_details
     'calc w = 1/[σ²(Fo²)+(0.0722P)²+0.3678P] 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     0.308
_refine_diff_density_min     -0.198
_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, 2003)'
_computing_cell_refinement     'SAINT (Bruker, 2003)'
_computing_data_reduction     'SAINT'
_computing_structure_solution     'SHELXS97 (Sheldrick, 1997a)'
_computing_structure_refinement     'SHELXL97 (Sheldrick, 1997a)'
_computing_molecular_graphics     'SHELXTL (Sheldrick, 1997b)'
_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
    C1 0.4528(3) -0.13740(18) 0.4983(3) 0.0791(7) Uani d . 1 . . C
    H1 0.4846 -0.1741 0.4539 0.095 Uiso calc R 1 . . H
    C2 0.3325(3) -0.09187(18) 0.4386(2) 0.0777(7) Uani d . 1 . . C
    H2 0.2826 -0.0983 0.3554 0.093 Uiso calc R 1 . . H
    C3 0.2867(2) -0.03594(14) 0.50518(18) 0.0572(5) Uani d . 1 . . C
    C4 0.3593(2) -0.02567(13) 0.62870(18) 0.0518(4) Uani d . 1 . . C
    C5 0.4808(2) -0.07449(15) 0.6867(2) 0.0605(5) Uani d . 1 . . C
    H5 0.5301 -0.0688 0.7701 0.073 Uiso calc R 1 . . H
    C6 0.5295(3) -0.13087(16) 0.6235(3) 0.0712(6) Uani d . 1 . . C
    C7 0.6605(3) -0.1828(2) 0.6854(3) 0.0970(9) Uani d . 1 . . C
    H7A 0.7156 -0.1672 0.6465 0.146 Uiso calc R 1 . . H
    H7B 0.6446 -0.2505 0.6804 0.146 Uiso calc R 1 . . H
    H7C 0.7049 -0.1639 0.7688 0.146 Uiso calc R 1 . . H
    C8 0.31050(18) 0.03658(13) 0.69621(16) 0.0482(4) Uani d . 1 . . C
    C9 0.18190(17) 0.08215(13) 0.62177(16) 0.0458(4) Uani d . 1 . . C
    C10 0.1207(2) 0.06672(14) 0.50249(17) 0.0533(5) Uani d . 1 . . C
    H10 0.0402 0.0982 0.4582 0.064 Uiso calc R 1 . . H
    C11 0.11957(17) 0.14996(13) 0.67667(16) 0.0470(4) Uani d . 1 . . C
    H11 0.0369 0.1750 0.6117 0.056 Uiso calc R 1 . . H
    C12 0.2199(2) 0.15738(16) 0.91390(18) 0.0613(5) Uani d . 1 . . C
    H12A 0.1922 0.1853 0.9711 0.074 Uiso calc R 1 . . H
    H12B 0.2903 0.1114 0.9566 0.074 Uiso calc R 1 . . H
    C13 0.26937(19) 0.23403(14) 0.85850(17) 0.0510(4) Uani d . 1 . . C
    C14 0.24323(17) 0.29129(12) 0.66110(16) 0.0448(4) Uani d . 1 . . C
    C15 0.14329(19) 0.33736(15) 0.56497(18) 0.0566(5) Uani d . 1 . . C
    H15 0.0555 0.3325 0.5536 0.068 Uiso calc R 1 . . H
    C16 0.1712(2) 0.39050(15) 0.48545(19) 0.0617(5) Uani d . 1 . . C
    H16 0.1030 0.4206 0.4198 0.074 Uiso calc R 1 . . H
    C17 0.3012(2) 0.39843(14) 0.50436(18) 0.0540(5) Uani d . 1 . . C
    C18 0.4035(2) 0.35463(15) 0.6009(2) 0.0585(5) Uani d . 1 . . C
    H18 0.4912 0.3612 0.6128 0.070 Uiso calc R 1 . . H
    C19 0.37468(18) 0.30067(14) 0.68015(18) 0.0521(4) Uani d . 1 . . C
    H19 0.4431 0.2708 0.7459 0.062 Uiso calc R 1 . . H
    Cl1 0.33525(7) 0.46507(5) 0.40205(6) 0.0827(2) Uani d . 1 . . Cl
    N1 0.20848(14) 0.23126(10) 0.73598(13) 0.0460(4) Uani d . 1 . . N
    O1 0.37359(14) 0.05043(12) 0.80520(12) 0.0646(4) Uani d . 1 . . O
    O2 0.16562(16) 0.00957(11) 0.44096(12) 0.0643(4) Uani d . 1 . . O
    O3 0.35456(14) 0.29216(11) 0.91807(12) 0.0630(4) Uani d . 1 . . O
    S1 0.08034(6) 0.09930(4) 0.79287(5) 0.06342(19) Uani d . 1 . . S
_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
    C1 C2 . 1.369(4) ?
    C1 C6 . 1.397(4) ?
    C1 H1 . 0.93 ?
    C2 C3 . 1.387(3) ?
    C2 H2 . 0.93 ?
    C3 C4 . 1.379(3) ?
    C3 O2 . 1.382(3) Yes
    C4 C5 . 1.400(3) ?
    C4 C8 . 1.468(3) ?
    C5 C6 . 1.380(3) ?
    C5 H5 . 0.93 ?
    C6 C7 . 1.503(4) ?
    C7 H7A . 0.96 ?
    C7 H7B . 0.96 ?
    C7 H7C . 0.96 ?
    C8 O1 . 1.225(2) yes
    C8 C9 . 1.463(3) yes
    C9 C10 . 1.336(3) yes
    C9 C11 . 1.505(3) yes
    C10 O2 . 1.344(3) yes
    C10 H10 . 0.93 ?
    C11 N1 . 1.473(2) yes
    C11 S1 . 1.8197(18) yes
    C11 H11 . 0.98 ?
    C12 C13 . 1.503(3) ?
    C12 S1 . 1.803(2) yes
    C12 H12A . 0.97 ?
    C12 H12B . 0.97 ?
    C13 O3 . 1.219(2) yes
    C13 N1 . 1.354(2) yes
    C14 C15 . 1.375(3) ?
    C14 C19 . 1.388(3) ?
    C14 N1 . 1.425(2) yes
    C15 C16 . 1.373(3) ?
    C15 H15 . 0.93 ?
    C16 C17 . 1.370(3) ?
    C16 H16 . 0.93 ?
    C17 C18 . 1.374(3) ?
    C17 Cl1 . 1.742(2) ?
    C18 C19 . 1.382(3) ?
    C18 H18 . 0.93 ?
    C19 H19 . 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
    C2 C1 C6 . . 122.5(2) ?
    C2 C1 H1 . . 118.7 ?
    C6 C1 H1 . . 118.7 ?
    C1 C2 C3 . . 118.5(2) ?
    C1 C2 H2 . . 120.8 ?
    C3 C2 H2 . . 120.8 ?
    C4 C3 O2 . . 122.00(19) ?
    C4 C3 C2 . . 121.5(2) ?
    O2 C3 C2 . . 116.5(2) ?
    C3 C4 C5 . . 118.3(2) ?
    C3 C4 C8 . . 120.32(19) ?
    C5 C4 C8 . . 121.37(18) ?
    C6 C5 C4 . . 121.8(2) ?
    C6 C5 H5 . . 119.1 ?
    C4 C5 H5 . . 119.1 ?
    C5 C6 C1 . . 117.4(2) ?
    C5 C6 C7 . . 122.0(3) ?
    C1 C6 C7 . . 120.7(2) ?
    C6 C7 H7A . . 109.5 ?
    C6 C7 H7B . . 109.5 ?
    H7A C7 H7B . . 109.5 ?
    C6 C7 H7C . . 109.5 ?
    H7A C7 H7C . . 109.5 ?
    H7B C7 H7C . . 109.5 ?
    O1 C8 C9 . . 123.03(18) ?
    O1 C8 C4 . . 122.65(18) ?
    C9 C8 C4 . . 114.31(16) ?
    C10 C9 C8 . . 119.96(18) ?
    C10 C9 C11 . . 119.03(17) ?
    C8 C9 C11 . . 120.96(15) ?
    C9 C10 O2 . . 125.56(19) ?
    C9 C10 H10 . . 117.2 ?
    O2 C10 H10 . . 117.2 ?
    N1 C11 C9 . . 111.39(14) yes
    N1 C11 S1 . . 104.79(12) yes
    C9 C11 S1 . . 115.60(13) yes
    N1 C11 H11 . . 108.3 ?
    C9 C11 H11 . . 108.3 ?
    S1 C11 H11 . . 108.3 ?
    C13 C12 S1 . . 107.61(13) yes
    C13 C12 H12A . . 110.2 ?
    S1 C12 H12A . . 110.2 ?
    C13 C12 H12B . . 110.2 ?
    S1 C12 H12B . . 110.2 ?
    H12A C12 H12B . . 108.5 ?
    O3 C13 N1 . . 124.19(19) ?
    O3 C13 C12 . . 123.27(17) ?
    N1 C13 C12 . . 112.55(17) yes
    C15 C14 C19 . . 119.64(18) ?
    C15 C14 N1 . . 118.95(16) ?
    C19 C14 N1 . . 121.35(16) ?
    C16 C15 C14 . . 120.92(18) ?
    C16 C15 H15 . . 119.5 ?
    C14 C15 H15 . . 119.5 ?
    C17 C16 C15 . . 118.93(19) ?
    C17 C16 H16 . . 120.5 ?
    C15 C16 H16 . . 120.5 ?
    C16 C17 C18 . . 121.42(19) ?
    C16 C17 Cl1 . . 118.51(16) ?
    C18 C17 Cl1 . . 120.06(16) ?
    C17 C18 C19 . . 119.40(18) ?
    C17 C18 H18 . . 120.3 ?
    C19 C18 H18 . . 120.3 ?
    C18 C19 C14 . . 119.66(18) ?
    C18 C19 H19 . . 120.2 ?
    C14 C19 H19 . . 120.2 ?
    C13 N1 C14 . . 124.09(15) yes
    C13 N1 C11 . . 118.00(15) yes
    C14 N1 C11 . . 116.83(13) yes
    C10 O2 C3 . . 117.83(15) yes
    C12 S1 C11 . . 93.10(9) 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_site_symmetry_1
    _geom_torsion_site_symmetry_2
    _geom_torsion_site_symmetry_3
    _geom_torsion_site_symmetry_4
    _geom_torsion
    _geom_torsion_publ_flag
    C6 C1 C2 C3 . . . . 1.1(4) ?
    C1 C2 C3 C4 . . . . -0.1(3) ?
    C1 C2 C3 O2 . . . . 179.3(2) ?
    O2 C3 C4 C5 . . . . 179.85(18) ?
    C2 C3 C4 C5 . . . . -0.9(3) ?
    O2 C3 C4 C8 . . . . -1.3(3) ?
    C2 C3 C4 C8 . . . . 177.94(19) ?
    C3 C4 C5 C6 . . . . 0.8(3) ?
    C8 C4 C5 C6 . . . . -177.99(19) ?
    C4 C5 C6 C1 . . . . 0.2(3) ?
    C4 C5 C6 C7 . . . . 179.5(2) ?
    C2 C1 C6 C5 . . . . -1.2(4) ?
    C2 C1 C6 C7 . . . . 179.5(3) ?
    C3 C4 C8 O1 . . . . -177.49(19) ?
    C5 C4 C8 O1 . . . . 1.3(3) ?
    C3 C4 C8 C9 . . . . 1.2(3) ?
    C5 C4 C8 C9 . . . . 179.97(17) ?
    O1 C8 C9 C10 . . . . 177.47(18) ?
    C4 C8 C9 C10 . . . . -1.2(2) ?
    O1 C8 C9 C11 . . . . 0.1(3) ?
    C4 C8 C9 C11 . . . . -178.56(15) ?
    C8 C9 C10 O2 . . . . 1.4(3) ?
    C11 C9 C10 O2 . . . . 178.82(17) ?
    C10 C9 C11 N1 . . . . -119.16(18) ?
    C8 C9 C11 N1 . . . . 58.2(2) ?
    C10 C9 C11 S1 . . . . 121.40(16) ?
    C8 C9 C11 S1 . . . . -61.23(19) ?
    S1 C12 C13 O3 . . . . 172.49(16) ?
    S1 C12 C13 N1 . . . . -7.2(2) ?
    C19 C14 C15 C16 . . . . 1.8(3) ?
    N1 C14 C15 C16 . . . . -175.39(18) ?
    C14 C15 C16 C17 . . . . -1.1(3) ?
    C15 C16 C17 C18 . . . . -0.1(3) ?
    C15 C16 C17 Cl1 . . . . 179.38(16) ?
    C16 C17 C18 C19 . . . . 0.6(3) ?
    Cl1 C17 C18 C19 . . . . -178.91(15) ?
    C17 C18 C19 C14 . . . . 0.1(3) ?
    C15 C14 C19 C18 . . . . -1.3(3) ?
    N1 C14 C19 C18 . . . . 175.81(17) ?
    O3 C13 N1 C14 . . . . 5.0(3) ?
    C12 C13 N1 C14 . . . . -175.34(16) ?
    O3 C13 N1 C11 . . . . 172.67(17) ?
    C12 C13 N1 C11 . . . . -7.6(2) ?
    C15 C14 N1 C13 . . . . -132.5(2) ?
    C19 C14 N1 C13 . . . . 50.3(3) ?
    C15 C14 N1 C11 . . . . 59.6(2) ?
    C19 C14 N1 C11 . . . . -117.53(19) ?
    C9 C11 N1 C13 . . . . -107.42(18) ?
    S1 C11 N1 C13 . . . . 18.27(19) ?
    C9 C11 N1 C14 . . . . 61.20(19) ?
    S1 C11 N1 C14 . . . . -173.11(12) ?
    C9 C10 O2 C3 . . . . -1.4(3) ?
    C4 C3 O2 C10 . . . . 1.4(3) ?
    C2 C3 O2 C10 . . . . -177.94(19) ?
    C13 C12 S1 C11 . . . . 15.02(15) ?
    N1 C11 S1 C12 . . . . -18.20(13) ?
    C9 C11 S1 C12 . . . . 104.80(14) ?
