##############################################################################
###                                                                        ###
###        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  #
# this CIF.  For information consult the CIF home page http://www.iucr.org/  #
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data_global
_audit_creation_method     SHELXL97
_journal_date_recd_electronic     2009-05-21
_journal_date_accepted     2009-05-28
_journal_name_full     'Acta Crystallographica, Section E'
_journal_year     2009
_journal_volume     65
_journal_issue      7
_journal_page_first     o1469
_journal_page_last     o1469
_journal_paper_category     QO
_journal_coeditor_code     XU2528
_publ_contact_author_name     'Professor Ping-Hsin Huang'
_publ_contact_author_address
;
Cardinal Tien College of Healthcare and Management
Taipei 231
Taiwan
;
_publ_contact_author_email     pshuang@ctcn.edu.tw
_publ_contact_author_fax     886-2-22192721
_publ_contact_author_phone     886-2-22191131
_publ_section_title
;
3,4-Dinitro-2,5-bis[4-(trifluoromethyl)phenyl]thiophene
;
loop_
    _publ_author_name
    _publ_author_address
    'Huang, Ping-Hsin'
;
Cardinal Tien College of Healthcare and Management
Taipei 231
Taiwan
;
    'Shen, Jiun-Yi'
;
Institute of Chemistry
Academia Sinica
Nankang
Taipei
Taiwan
;
    'Wen, Yuh-Sheng'
;
Institute of Chemistry
Academia Sinica
Nankang
Taipei
Taiwan
;
data_I
_chemical_name_systematic
;
3,4-Dinitro-2,5-bis[4-(trifluoromethyl)phenyl]thiophene
;
_chemical_name_common     ?
_chemical_formula_moiety     'C18 H8 F6 N2 O4 S'
_chemical_formula_sum     'C18 H8 F6 N2 O4 S'
_chemical_formula_iupac     'C18 H8 F6 N2 O4 S'
_chemical_formula_weight     462.32
_chemical_melting_point     ?
_symmetry_cell_setting     orthorhombic
_symmetry_space_group_name_H-M     'P b c a'
_symmetry_space_group_name_Hall     '-P 2ac 2ab'
loop_
    _symmetry_equiv_pos_as_xyz
    'x, y, z'
    '-x+1/2, -y, z+1/2'
    'x+1/2, -y+1/2, -z'
    '-x, y+1/2, -z+1/2'
    '-x, -y, -z'
    'x-1/2, y, -z-1/2'
    '-x-1/2, y-1/2, z'
    'x, -y-1/2, z-1/2'
_cell_length_a     8.1572(3)
_cell_length_b     17.6371(6)
_cell_length_c     24.4150(8)
_cell_angle_alpha     90.00
_cell_angle_beta     90.00
_cell_angle_gamma     90.00
_cell_volume     3512.6(2)
_cell_formula_units_Z     8
_cell_measurement_reflns_used     3689
_cell_measurement_theta_min     2.31
_cell_measurement_theta_max     21.23
_cell_measurement_temperature     100.00(10)
_exptl_crystal_description     plate
_exptl_crystal_colour     colourless
_exptl_crystal_size_max     0.4
_exptl_crystal_size_mid     0.36
_exptl_crystal_size_min     0.1
_exptl_crystal_density_diffrn     1.748
_exptl_crystal_density_meas     ?
_exptl_crystal_density_method     'not measured'
_exptl_crystal_F_000     1856
_exptl_absorpt_coefficient_mu     0.278
_exptl_absorpt_correction_type     multi-scan
_exptl_absorpt_process_details     '(SADABS; Bruker, 2001)'
_exptl_absorpt_correction_T_min     0.8948
_exptl_absorpt_correction_T_max     0.9732
_exptl_special_details
;
¹H NMR (CDCl₃):
7.77 (d, J = 8.2, 4H), 7.64 (d, J = 8.2, 4H). FAB MS (m/e): 462 (M⁺).
Analysis calculated for C₁₈H₈F₆N₂O₄S: C 46.76, H 1.74, N 6.06%;
found: C 46.80, H 1.88, N 5.79%.
;
_diffrn_ambient_temperature     100.00(10)
_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     'ω and φ'
_diffrn_detector_area_resol_mean     ?
_diffrn_reflns_number     22650
_diffrn_reflns_av_R_equivalents     0.0582
_diffrn_reflns_av_sigmaI/netI     0.0729
_diffrn_reflns_theta_min     1.67
_diffrn_reflns_theta_max     25.03
_diffrn_reflns_theta_full     25.03
_diffrn_measured_fraction_theta_max     1.000
_diffrn_measured_fraction_theta_full     1.000
_diffrn_reflns_limit_h_min     -8
_diffrn_reflns_limit_h_max     9
_diffrn_reflns_limit_k_min     -20
_diffrn_reflns_limit_k_max     20
_diffrn_reflns_limit_l_min     -29
_diffrn_reflns_limit_l_max     29
_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 >
σ(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     3098
_reflns_number_gt     1888
_reflns_threshold_expression     I>2σ(I)
_refine_ls_structure_factor_coef     Fsqd
_refine_ls_matrix_type     full
_refine_ls_R_factor_all     0.0554
_refine_ls_R_factor_gt     0.0300
_refine_ls_wR_factor_gt     0.0509
_refine_ls_wR_factor_ref     0.0534
_refine_ls_goodness_of_fit_ref     0.804
_refine_ls_restrained_S_all     0.804
_refine_ls_number_reflns     3098
_refine_ls_number_parameters     281
_refine_ls_number_restraints     0
_refine_ls_hydrogen_treatment     constr
_refine_ls_weighting_scheme     calc
_refine_ls_weighting_details
               'calc w = 1/[σ²(Fo²)+(0.0222P)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     0.000
_refine_ls_shift/su_mean     0.000
_refine_diff_density_max     0.285
_refine_diff_density_min     -0.280
_refine_ls_extinction_method     'SHELXL97 (Sheldrick, 2008)'
_refine_ls_extinction_coef     0.00042(7)
_refine_ls_extinction_expression
                                  'Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^'
loop_
    _atom_type_symbol
    _atom_type_description
    _atom_type_scat_dispersion_real
    _atom_type_scat_dispersion_imag
    _atom_type_scat_source
    'S' 'S' 0.1246 0.1234
                         'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
    'F' 'F' 0.0171 0.0103
                         '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'
    'N' 'N' 0.0061 0.0033
                         'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
    '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'
_computing_data_collection     'SMART (Bruker, 2001)'
_computing_cell_refinement     'SAINT (Bruker, 2001)'
_computing_data_reduction     'SAINT (Bruker, 2001'
_computing_structure_solution     'SHELXS97 (Sheldrick, 2008)'
_computing_structure_refinement     'SHELXL97 (Sheldrick, 2008)'
_computing_molecular_graphics     'ORTEP-3 for Windows (Farrugia, 1997)'
_computing_publication_material     'WinGX (Farrugia, 1999)'
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 S 0.49028(6) 0.16607(3) 0.10370(2) 0.01968(14) Uani d . 1 . .
    F F1 0.35605(13) 0.58240(6) 0.14011(4) 0.0308(3) Uani d . 1 . .
    F F2 0.55441(13) 0.58514(6) 0.08266(5) 0.0355(3) Uani d . 1 . .
    F F3 0.31448(13) 0.55311(6) 0.05612(4) 0.0317(3) Uani d . 1 . .
    F F4 0.39559(15) -0.25593(7) 0.10705(5) 0.0436(4) Uani d . 1 . .
    F F5 0.59498(14) -0.24370(7) 0.05129(5) 0.0414(4) Uani d . 1 . .
    F F6 0.35364(14) -0.21365(7) 0.02679(5) 0.0421(4) Uani d . 1 . .
    O O1 0.84762(17) 0.29479(8) 0.21049(6) 0.0336(4) Uani d . 1 . .
    O O2 0.72134(16) 0.23172(8) 0.27348(6) 0.0327(4) Uani d . 1 . .
    O O3 0.89423(17) 0.10570(8) 0.23361(6) 0.0326(4) Uani d . 1 . .
    O O4 0.72044(15) 0.01316(8) 0.23007(5) 0.0227(4) Uani d . 1 . .
    N N2 0.75230(19) 0.24606(10) 0.22593(7) 0.0206(4) Uani d . 1 . .
    N N3 0.7648(2) 0.07741(10) 0.21850(6) 0.0198(4) Uani d . 1 . .
    C C1 0.5770(2) 0.23578(11) 0.14335(7) 0.0154(5) Uani d . 1 . .
    C C2 0.6654(2) 0.20278(11) 0.18389(8) 0.0152(5) Uani d . 1 . .
    C C3 0.6626(2) 0.12295(11) 0.18302(7) 0.0151(5) Uani d . 1 . .
    C C4 0.5731(2) 0.09335(10) 0.14100(7) 0.0145(5) Uani d . 1 . .
    C C11 0.5395(2) 0.31580(10) 0.13231(8) 0.0153(5) Uani d . 1 . .
    C C12 0.5170(2) 0.36726(11) 0.17431(8) 0.0177(5) Uani d . 1 . .
    H H12 0.5278 0.3514 0.2105 0.021 Uiso calc R 1 . .
    C C13 0.4788(2) 0.44149(11) 0.16326(8) 0.0182(5) Uani d . 1 . .
    H H13 0.4654 0.4758 0.1918 0.022 Uiso calc R 1 . .
    C C14 0.4601(2) 0.46509(11) 0.10993(8) 0.0169(5) Uani d . 1 . .
    C C15 0.4800(2) 0.41410(11) 0.06754(8) 0.0213(5) Uani d . 1 . .
    H H15 0.4659 0.4299 0.0315 0.026 Uiso calc R 1 . .
    C C16 0.5204(2) 0.34036(11) 0.07853(8) 0.0203(5) Uani d . 1 . .
    H H16 0.5353 0.3064 0.0498 0.024 Uiso calc R 1 . .
    C C17 0.4211(2) 0.54560(12) 0.09785(9) 0.0225(5) Uani d . 1 . .
    C C21 0.5441(2) 0.01459(11) 0.12329(8) 0.0154(5) Uani d . 1 . .
    C C22 0.5951(2) -0.00879(11) 0.07186(8) 0.0191(5) Uani d . 1 . .
    H H22 0.6485 0.0252 0.0488 0.023 Uiso calc R 1 . .
    C C23 0.5672(2) -0.08169(11) 0.05477(8) 0.0204(5) Uani d . 1 . .
    H H23 0.6030 -0.0973 0.0204 0.024 Uiso calc R 1 . .
    C C24 0.4859(2) -0.13201(11) 0.08861(7) 0.0167(5) Uani d . 1 . .
    C C25 0.4314(2) -0.10885(11) 0.13930(8) 0.0182(5) Uani d . 1 . .
    H H25 0.3749 -0.1424 0.1618 0.022 Uiso calc R 1 . .
    C C26 0.4607(2) -0.03585(11) 0.15652(8) 0.0171(5) Uani d . 1 . .
    H H26 0.4242 -0.0203 0.1908 0.021 Uiso calc R 1 . .
    C C27 0.4586(3) -0.21090(12) 0.06936(9) 0.0249(5) Uani d . 1 . .
_geom_special_details
;
All e.s.d.'s (except the e.s.d. in the dihedral angle between two l.s. planes)
are estimated using the full covariance matrix. The cell e.s.d.'s are taken
into account individually in the estimation of e.s.d.'s in distances, angles
and torsion angles; correlations between e.s.d.'s in cell parameters are only
used when they are defined by crystal symmetry. An approximate (isotropic)
treatment of cell e.s.d.'s is used for estimating e.s.d.'s 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
    S C4 . 1.7119(19) ?
    S C1 . 1.7173(19) ?
    F1 C17 . 1.329(2) ?
    F2 C17 . 1.344(2) ?
    F3 C17 . 1.346(2) ?
    F4 C27 . 1.320(2) ?
    F5 C27 . 1.330(2) ?
    F6 C27 . 1.347(2) ?
    O1 N2 . 1.2187(19) ?
    O2 N2 . 1.2147(18) ?
    O3 N3 . 1.2249(18) ?
    O4 N3 . 1.2226(18) ?
    N2 C2 . 1.462(2) ?
    N3 C3 . 1.446(2) ?
    C1 C2 . 1.356(2) ?
    C1 C11 . 1.469(2) ?
    C2 C3 . 1.408(2) ?
    C3 C4 . 1.363(2) ?
    C4 C21 . 1.474(2) ?
    C11 C12 . 1.382(2) ?
    C11 C16 . 1.391(2) ?
    C12 C13 . 1.373(2) ?
    C12 H12 . 0.9300 ?
    C13 C14 . 1.375(2) ?
    C13 H13 . 0.9300 ?
    C14 C15 . 1.381(2) ?
    C14 C17 . 1.485(3) ?
    C15 C16 . 1.368(3) ?
    C15 H15 . 0.9300 ?
    C16 H16 . 0.9300 ?
    C21 C26 . 1.383(2) ?
    C21 C22 . 1.386(2) ?
    C22 C23 . 1.371(3) ?
    C22 H22 . 0.9300 ?
    C23 C24 . 1.382(3) ?
    C23 H23 . 0.9300 ?
    C24 C25 . 1.377(2) ?
    C24 C27 . 1.485(3) ?
    C25 C26 . 1.375(2) ?
    C25 H25 . 0.9300 ?
    C26 H26 . 0.9300 ?
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
    C4 S C1 . . 94.24(9) ?
    O2 N2 O1 . . 125.10(17) ?
    O2 N2 C2 . . 117.48(17) ?
    O1 N2 C2 . . 117.40(17) ?
    O4 N3 O3 . . 124.26(17) ?
    O4 N3 C3 . . 118.87(17) ?
    O3 N3 C3 . . 116.82(17) ?
    C2 C1 C11 . . 131.07(18) ?
    C2 C1 S . . 108.86(14) ?
    C11 C1 S . . 119.92(14) ?
    C1 C2 C3 . . 114.15(17) ?
    C1 C2 N2 . . 123.10(18) ?
    C3 C2 N2 . . 122.72(18) ?
    C4 C3 C2 . . 113.78(17) ?
    C4 C3 N3 . . 123.16(18) ?
    C2 C3 N3 . . 122.46(18) ?
    C3 C4 C21 . . 131.90(18) ?
    C3 C4 S . . 108.95(14) ?
    C21 C4 S . . 119.11(14) ?
    C12 C11 C16 . . 118.74(18) ?
    C12 C11 C1 . . 121.51(17) ?
    C16 C11 C1 . . 119.71(17) ?
    C13 C12 C11 . . 120.72(17) ?
    C13 C12 H12 . . 119.6 ?
    C11 C12 H12 . . 119.6 ?
    C12 C13 C14 . . 119.99(18) ?
    C12 C13 H13 . . 120.0 ?
    C14 C13 H13 . . 120.0 ?
    C13 C14 C15 . . 119.97(19) ?
    C13 C14 C17 . . 120.08(18) ?
    C15 C14 C17 . . 119.94(18) ?
    C16 C15 C14 . . 120.02(18) ?
    C16 C15 H15 . . 120.0 ?
    C14 C15 H15 . . 120.0 ?
    C15 C16 C11 . . 120.54(18) ?
    C15 C16 H16 . . 119.7 ?
    C11 C16 H16 . . 119.7 ?
    F1 C17 F2 . . 106.49(16) ?
    F1 C17 F3 . . 106.33(16) ?
    F2 C17 F3 . . 105.24(16) ?
    F1 C17 C14 . . 113.47(17) ?
    F2 C17 C14 . . 112.20(16) ?
    F3 C17 C14 . . 112.51(17) ?
    C26 C21 C22 . . 119.21(18) ?
    C26 C21 C4 . . 120.86(17) ?
    C22 C21 C4 . . 119.88(17) ?
    C23 C22 C21 . . 120.34(19) ?
    C23 C22 H22 . . 119.8 ?
    C21 C22 H22 . . 119.8 ?
    C22 C23 C24 . . 120.00(18) ?
    C22 C23 H23 . . 120.0 ?
    C24 C23 H23 . . 120.0 ?
    C25 C24 C23 . . 120.11(18) ?
    C25 C24 C27 . . 120.92(18) ?
    C23 C24 C27 . . 118.97(18) ?
    C26 C25 C24 . . 119.76(18) ?
    C26 C25 H25 . . 120.1 ?
    C24 C25 H25 . . 120.1 ?
    C25 C26 C21 . . 120.55(18) ?
    C25 C26 H26 . . 119.7 ?
    C21 C26 H26 . . 119.7 ?
    F4 C27 F5 . . 107.18(18) ?
    F4 C27 F6 . . 105.61(16) ?
    F5 C27 F6 . . 105.08(16) ?
    F4 C27 C24 . . 113.67(17) ?
    F5 C27 C24 . . 112.76(17) ?
    F6 C27 C24 . . 111.91(18) ?
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
    C13 H13 O4 4_655 0.93 2.52 3.320(2) 144 yes
