##############################################################################
###                                                                        ###
###        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     'SHELXL97'
_journal_date_recd_electronic     2007-10-29
_journal_date_accepted     2007-10-29
_journal_name_full     'Acta Crystallographica, Section E'
_journal_year     2007
_journal_volume     63
_journal_issue     12
_journal_page_first     o4568
_journal_page_last     o4569
_journal_paper_category     QO
_journal_coeditor_code     NG2356
_publ_contact_author_name     'Tomura, Masaaki'
_publ_contact_author_address
;
Institute for Molecular Science
Myodaiji, Okazaki 444-8585, Japan
;
_publ_contact_author_email     tomura@ims.ac.jp
_publ_contact_author_fax     '+81-564-53-5728'
_publ_contact_author_phone     '+81-564-55-7486'
_publ_section_title
;\
2H,10H-1,4-Dioxepino[5',6':4,5]thieno[3,2-e][1,4]\
dioxepine-5,7(3H,9H)-dione
;
loop_
    _publ_author_name
    _publ_author_address
    'Tomura, Masaaki'
;
Institute for Molecular Science
Myodaiji
Okazaki 444-8585
Japan
;
    'Ono, Katsuhiko'
;
Department of Materials Science and Engineering
Nagoya Institute of Technology
Gokiso
Showa-ku
Nagoya 466-8555
Japan
;
    'Kaiden, Masanori'
;
Department of Materials Science and Engineering
Nagoya Institute of Technology
Gokiso
Showa-ku
Nagoya 466-8555
Japan
;
    'Tsukamoto, Kenichi'
;
Department of Materials Science and Engineering
Nagoya Institute of Technology
Gokiso
Showa-ku
Nagoya 466-8555
Japan
;
    'Saito, Katsuhiro'
;
Department of Materials Science and Engineering
Nagoya Institute of Technology
Gokiso
Showa-ku
Nagoya 466-8555
Japan
;
data_I
_chemical_name_systematic
;
2H,10H-1,4-Dioxepino[5',6':4,5]thieno[3,2-
e][1,4]dioxepine-5,7(3H,9H)-dione
;
_chemical_name_common     ?
_chemical_formula_moiety     'C10 H8 O6 S'
_chemical_formula_sum     'C10 H8 O6 S'
_chemical_formula_iupac     'C10 H8 O6 S'
_chemical_formula_weight     256.22
_chemical_melting_point     '>573'
_symmetry_cell_setting     orthorhombic
_symmetry_space_group_name_H-M     'P n m a'
_symmetry_space_group_name_Hall     '-P 2ac 2n'
loop_
    _symmetry_equiv_pos_as_xyz
    'x, y, z'
    'x+1/2, -y+1/2, -z+1/2'
    '-x, y+1/2, -z'
    '-x+1/2, -y, z+1/2'
    '-x, -y, -z'
    '-x-1/2, y-1/2, z-1/2'
    'x, -y-1/2, z'
    'x-1/2, y, -z-1/2'
_cell_length_a     20.301(2)
_cell_length_b     6.9037(8)
_cell_length_c     7.3463(8)
_cell_angle_alpha     90.00
_cell_angle_beta     90.00
_cell_angle_gamma     90.00
_cell_volume     1029.6(2)
_cell_formula_units_Z     4
_cell_measurement_reflns_used     2531
_cell_measurement_theta_min     3.0088
_cell_measurement_theta_max     27.4835
_cell_measurement_temperature     296(2)
_exptl_crystal_description     'Prism'
_exptl_crystal_colour     'Colorless'
_exptl_crystal_size_max     0.25
_exptl_crystal_size_mid     0.25
_exptl_crystal_size_min     0.10
_exptl_crystal_density_diffrn     1.653
_exptl_crystal_density_meas     ?
_exptl_crystal_density_method     'not measured'
_exptl_crystal_F_000     528
_exptl_absorpt_coefficient_mu     0.329
_exptl_absorpt_correction_type     none
_exptl_special_details
;
 ?
;
_diffrn_ambient_temperature     296(2)
_diffrn_radiation_type     MoK\a
_diffrn_radiation_wavelength     0.71070
_diffrn_radiation_source     'Rotating Anode'
_diffrn_radiation_monochromator     'Graphite Monochromator'
_diffrn_measurement_device_type     'Rigaku/MSC Mercury CCD'
_diffrn_measurement_method     'φ & ω scans'
_diffrn_detector_area_resol_mean     14.6199
_diffrn_reflns_number     7769
_diffrn_reflns_av_R_equivalents     0.0378
_diffrn_reflns_av_sigmaI/netI     0.0225
_diffrn_reflns_theta_min     3.42
_diffrn_reflns_theta_max     27.47
_diffrn_reflns_theta_full     27.47
_diffrn_measured_fraction_theta_max     0.977
_diffrn_measured_fraction_theta_full     0.977
_diffrn_reflns_limit_h_min     -26
_diffrn_reflns_limit_h_max     23
_diffrn_reflns_limit_k_min     -8
_diffrn_reflns_limit_k_max     8
_diffrn_reflns_limit_l_min     -6
_diffrn_reflns_limit_l_max     9
_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     1246
_reflns_number_gt     1222
_reflns_threshold_expression     'I>2σ(I)'
_refine_ls_structure_factor_coef     Fsqd
_refine_ls_matrix_type     full
_refine_ls_R_factor_all     0.0679
_refine_ls_R_factor_gt     0.0656
_refine_ls_wR_factor_gt     0.1493
_refine_ls_wR_factor_ref     0.1506
_refine_ls_goodness_of_fit_ref     1.121
_refine_ls_restrained_S_all     1.105
_refine_ls_number_reflns     1246
_refine_ls_number_parameters     115
_refine_ls_number_restraints     39
_refine_ls_hydrogen_treatment     constr
_refine_ls_weighting_scheme     calc
_refine_ls_weighting_details
         'calc w=1/[σ²(Fo²)+(0.1532P)²+1.2875P] 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     0.003
_refine_ls_shift/su_mean     0.000
_refine_diff_density_max     0.241
_refine_diff_density_min     -0.284
_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'
    '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'
_computing_data_collection
;
CrystalClear (Molecular Structure Corporation & Rigaku,2001)
;
_computing_cell_refinement
;
CrystalClear (Molecular Structure Corporation & Rigaku, 2001)
;
_computing_data_reduction
;
TEXSAN (Molecular Structure Corporation & Rigaku, 2000)
;
_computing_structure_solution     'SHELXS97 (Sheldrick, 1997)'
_computing_structure_refinement     'SHELXL97 (Sheldrick, 1997)'
_computing_molecular_graphics     'PLATON (Spek, 2003)'
_computing_publication_material     'SHELXL97 (Sheldrick, 1997)'
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 0.03443(5) 0.2500 0.59051(10) 0.0415(3) Uani d S 1 A .
    O O1 0.16771(17) 0.2500 0.7229(4) 0.0830(12) Uani d SU 1 A .
    O O2 0.22262(18) 0.1835(6) 0.4789(5) 0.0626(14) Uani d PU 0.50 A -1
    O O3 0.12917(14) 0.2500 0.1296(3) 0.0647(9) Uani d SU 1 . .
    O O4 -0.10643(16) 0.2500 0.5961(4) 0.0637(8) Uani d SU 1 . .
    O O5 -0.13039(15) 0.2500 0.3096(4) 0.0825(12) Uani d SU 1 . .
    O O6 0.00129(15) 0.2500 0.0697(3) 0.0829(13) Uani d SU 1 . .
    C C1 0.10475(18) 0.2500 0.4587(4) 0.0393(7) Uani d SU 1 A .
    C C2 0.08960(18) 0.2500 0.2764(4) 0.0436(8) Uani d SU 1 . .
    C C3 0.02063(18) 0.2500 0.2444(4) 0.0446(8) Uani d SU 1 B .
    C C4 -0.01558(18) 0.2500 0.4004(4) 0.0382(7) Uani d SU 1 . .
    C C5 0.1665(2) 0.2500 0.5615(5) 0.0551(10) Uani d SU 1 . .
    C C6 0.2204(3) 0.1130(11) 0.2935(8) 0.0624(15) Uani d PU 0.50 A -1
    H H6A 0.1911 0.0020 0.2890 0.075 Uiso calc PR 0.50 A -1
    H H6B 0.2641 0.0684 0.2601 0.075 Uiso calc PR 0.50 A -1
    C C7 0.1991(2) 0.2500 0.1616(6) 0.0687(13) Uani d SU 1 . .
    H H7A 0.2215 0.2234 0.0476 0.082 Uiso calc PR 0.50 A .
    H H7B 0.2123 0.3784 0.2011 0.082 Uiso calc PR 0.50 . .
    C C8 -0.08665(19) 0.2500 0.4417(5) 0.0452(8) Uani d SU 1 B .
    C C9 -0.1102(3) 0.1692(10) 0.1254(7) 0.0619(15) Uani d PU 0.50 B -1
    H H9A -0.0861 0.0488 0.1399 0.074 Uiso calc PR 0.50 B -1
    H H9B -0.1486 0.1453 0.0502 0.074 Uiso calc PR 0.50 B -1
    C C10 -0.0673(3) 0.3208(10) 0.0416(7) 0.0599(18) Uani d PU 0.50 B -1
    H H10A -0.0769 0.3347 -0.0871 0.072 Uiso calc PR 0.50 B -1
    H H10B -0.0738 0.4449 0.1008 0.072 Uiso calc PR 0.50 B -1
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
    S1 0.0580(6) 0.0389(5) 0.0277(4) 0.000 0.0007(3) 0.000
    O1 0.077(2) 0.135(3) 0.0370(14) 0.000 -0.0137(14) 0.000
    O2 0.0498(19) 0.092(4) 0.0462(18) -0.0018(18) -0.0067(15) 0.0049(18)
    O3 0.0526(16) 0.111(3) 0.0304(12) 0.000 0.0031(11) 0.000
    O4 0.0643(18) 0.082(2) 0.0452(15) 0.000 0.0140(13) 0.000
    O5 0.0471(17) 0.154(4) 0.0467(16) 0.000 0.0001(13) 0.000
    O6 0.0514(17) 0.168(4) 0.0289(13) 0.000 -0.0037(11) 0.000
    C1 0.0520(19) 0.0342(17) 0.0317(14) 0.000 -0.0017(13) 0.000
    C2 0.054(2) 0.047(2) 0.0293(15) 0.000 0.0005(13) 0.000
    C3 0.050(2) 0.054(2) 0.0292(15) 0.000 -0.0043(13) 0.000
    C4 0.0517(18) 0.0304(15) 0.0326(15) 0.000 -0.0003(13) 0.000
    C5 0.057(2) 0.070(3) 0.0378(18) 0.000 -0.0049(16) 0.000
    C6 0.046(3) 0.084(4) 0.057(3) 0.004(3) 0.004(2) -0.008(3)
    C7 0.051(2) 0.107(4) 0.048(2) 0.000 0.0029(18) 0.000
    C8 0.052(2) 0.0413(19) 0.0425(18) 0.000 0.0015(15) 0.000
    C9 0.055(3) 0.080(4) 0.051(3) 0.003(3) -0.012(2) -0.011(3)
    C10 0.056(3) 0.090(5) 0.034(2) 0.010(3) -0.011(2) 0.004(2)
_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 C1 . 1.725(4) ?
    S1 C4 . 1.727(3) ?
    O1 C5 . 1.186(4) ?
    O2 C6 . 1.447(6) ?
    O2 C5 . 1.370(5) ?
    O3 C2 . 1.345(4) ?
    O3 C7 . 1.439(5) ?
    O4 C8 . 1.204(4) ?
    O5 C8 . 1.315(5) ?
    O5 C9 7_565 1.520(6) no
    O5 C9 . 1.520(6) ?
    O6 C3 . 1.342(4) ?
    O6 C10 . 1.491(6) ?
    O6 C10 7_565 1.491(6) no
    C1 C2 . 1.375(4) ?
    C1 C5 . 1.463(5) ?
    C2 C3 . 1.420(5) ?
    C3 C4 . 1.361(5) ?
    C4 C8 . 1.474(5) ?
    C5 O2 7_565 1.370(5) no
    C6 C7 . 1.421(7) ?
    C6 H6A . 0.9700 no
    C6 H6B . 0.9700 no
    C7 C6 7_565 1.421(7) no
    C7 H7A . 0.9700 no
    C7 H7B . 0.9700 no
    C9 C10 . 1.494(8) ?
    C9 H9A . 0.9700 no
    C9 H9B . 0.9700 no
    C10 H10A . 0.9700 no
    C10 H10B . 0.9700 no
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 S1 C4 . . 91.88(16) ?
    C6 O2 C5 . . 120.2(4) no
    C2 O3 C7 . . 117.3(3) no
    C8 O5 C9 . 7_565 118.3(3) no
    C8 O5 C9 . . 118.3(3) no
    C3 O6 C10 . . 113.9(3) no
    C3 O6 C10 . 7_565 113.9(3) no
    C2 C1 C5 . . 134.0(3) no
    C2 C1 S1 . . 111.2(3) ?
    C5 C1 S1 . . 114.8(2) no
    O3 C2 C1 . . 130.4(3) no
    O3 C2 C3 . . 117.2(3) no
    C1 C2 C3 . . 112.4(3) ?
    O6 C3 C4 . . 130.3(3) no
    O6 C3 C2 . . 116.5(3) no
    C4 C3 C2 . . 113.2(3) ?
    C3 C4 C8 . . 134.6(3) no
    C3 C4 S1 . . 111.3(3) ?
    C8 C4 S1 . . 114.1(2) no
    O1 C5 C1 . . 122.2(4) no
    O1 C5 O2 . 7_565 115.2(4) no
    C1 C5 O2 . 7_565 119.0(3) no
    O1 C5 O2 . . 115.2(4) no
    C1 C5 O2 . . 119.0(3) no
    O2 C6 C7 . . 115.3(5) no
    O2 C6 H6A . . 108.4 no
    C7 C6 H6A . . 108.4 no
    O2 C6 H6B . . 108.4 no
    C7 C6 H6B . . 108.4 no
    H6A C6 H6B . . 107.5 no
    C6 C7 C6 7_565 . 83.4(6) no
    C6 C7 O3 7_565 . 114.3(3) no
    C6 C7 O3 . . 114.3(3) no
    C6 C7 H7A 7_565 . 124.9 no
    C6 C7 H7A . . 108.7 no
    O3 C7 H7A . . 108.7 no
    C6 C7 H7B . . 108.7 no
    O3 C7 H7B . . 108.7 no
    H7A C7 H7B . . 107.6 no
    O4 C8 O5 . . 118.0(4) no
    O4 C8 C4 . . 121.4(3) no
    O5 C8 C4 . . 120.6(3) no
    C10 C9 O5 . . 105.5(4) no
    C10 C9 H9A . . 110.6 no
    O5 C9 H9A . . 110.6 no
    C10 C9 H9B . . 110.6 no
    O5 C9 H9B . . 110.6 no
    H9A C9 H9B . . 108.8 no
    O6 C10 C9 . . 104.9(4) no
    O6 C10 H10A . . 110.8 no
    C9 C10 H10A . . 110.8 no
    O6 C10 H10B . . 110.8 no
    C9 C10 H10B . . 110.8 no
    H10A C10 H10B . . 108.8 no
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 S1 C1 C2 . . . . 0.0 no
    C4 S1 C1 C5 . . . . 180.0 no
    C7 O3 C2 C1 . . . . 0.0 no
    C7 O3 C2 C3 . . . . 180.0 no
    C5 C1 C2 O3 . . . . 0.0 no
    S1 C1 C2 O3 . . . . 180.0 no
    C5 C1 C2 C3 . . . . 180.0 no
    S1 C1 C2 C3 . . . . 0.0 no
    C10 O6 C3 C4 . . . . 21.0(3) no
    C10 O6 C3 C4 7_565 . . . -21.0(3) no
    C10 O6 C3 C2 . . . . -159.0(3) no
    C10 O6 C3 C2 7_565 . . . 159.0(3) no
    O3 C2 C3 O6 . . . . 0.0 no
    C1 C2 C3 O6 . . . . 180.0 no
    O3 C2 C3 C4 . . . . 180.0 no
    C1 C2 C3 C4 . . . . 0.0 no
    O6 C3 C4 C8 . . . . 0.0 no
    C2 C3 C4 C8 . . . . 180.0 no
    O6 C3 C4 S1 . . . . 180.0 no
    C2 C3 C4 S1 . . . . 0.0 no
    C1 S1 C4 C3 . . . . 0.0 no
    C1 S1 C4 C8 . . . . 180.0 no
    C2 C1 C5 O1 . . . . 180.0 no
    S1 C1 C5 O1 . . . . 0.0 no
    C2 C1 C5 O2 . . . 7_565 22.5(2) no
    S1 C1 C5 O2 . . . 7_565 -157.5(2) no
    C2 C1 C5 O2 . . . . -22.5(2) no
    S1 C1 C5 O2 . . . . 157.5(2) no
    C6 O2 C5 O1 . . . . 158.5(4) no
    C6 O2 C5 C1 . . . . -0.5(5) no
    C6 O2 C5 O2 . . . 7_565 -101.9(4) no
    C5 O2 C6 C7 . . . . 60.1(6) no
    O2 C6 C7 C6 . . . 7_565 23.1(6) no
    O2 C6 C7 O3 . . . . -90.6(5) no
    C2 O3 C7 C6 . . . 7_565 -46.9(4) no
    C2 O3 C7 C6 . . . . 46.9(4) no
    C9 O5 C8 O4 7_565 . . . 155.4(3) no
    C9 O5 C8 O4 . . . . -155.4(3) no
    C9 O5 C8 C4 7_565 . . . -24.6(3) no
    C9 O5 C8 C4 . . . . 24.6(3) no
    C3 C4 C8 O4 . . . . 180.0 no
    S1 C4 C8 O4 . . . . 0.0 no
    C3 C4 C8 O5 . . . . 0.0 no
    S1 C4 C8 O5 . . . . 180.0 no
    C8 O5 C9 C10 . . . . -75.3(4) no
    C9 O5 C9 C10 7_565 . . . 27.0(4) no
    C3 O6 C10 C9 . . . . -68.2(4) no
    C10 O6 C10 C9 7_565 . . . 30.7(4) no
    O5 C9 C10 O6 . . . . 101.2(4) no
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
    C6 H6A O4 3_546 0.97 2.59 3.506(7) 158.0 yes
    C10 H10A O4 1_554 0.97 2.47 3.403(6) 160.4 yes
    C6 H6B O5 2 0.97 2.53 3.262(7) 131.8 yes
    C6 H6B O1 4_554 0.97 2.61 3.422(7) 141.1 yes
