#------------------------------------------------------------------------------
#$Date: 2017-10-13 11:42:48 +0300 (Fri, 13 Oct 2017) $
#$Revision: 201978 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/22/24/2222499.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/. The original data for this entry
# were provided by IUCr Journals, http://journals.iucr.org/.
#
# The file may be used within the scientific community so long as
# proper attribution is given to the journal article from which the
# data were obtained.
#
data_2222499
loop_
_publ_author_name
'Huang, Ping-Hsin'
'Shen, Jiun-Yi'
'Wen, Yuh-Sheng'
_publ_section_title
;
 3,4-Dinitro-2,5-bis[4-(trifluoromethyl)phenyl]thiophene
;
_journal_coeditor_code           XU2528
_journal_issue                   7
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o1469
_journal_paper_doi               10.1107/S1600536809020443
_journal_volume                  65
_journal_year                    2009
_chemical_formula_iupac          'C18 H8 F6 N2 O4 S'
_chemical_formula_moiety         'C18 H8 F6 N2 O4 S'
_chemical_formula_sum            'C18 H8 F6 N2 O4 S'
_chemical_formula_weight         462.32
_chemical_name_systematic
;
3,4-Dinitro-2,5-bis[4-(trifluoromethyl)phenyl]thiophene
;
_space_group_IT_number           61
_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_Hall  '-P 2ac 2ab'
_symmetry_space_group_name_H-M   'P b c a'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_formula_units_Z            8
_cell_length_a                   8.1572(3)
_cell_length_b                   17.6371(6)
_cell_length_c                   24.4150(8)
_cell_measurement_reflns_used    3689
_cell_measurement_temperature    100.00(10)
_cell_measurement_theta_max      21.23
_cell_measurement_theta_min      2.31
_cell_volume                     3512.6(2)
_computing_cell_refinement       'SAINT (Bruker, 2001)'
_computing_data_collection       'SMART (Bruker, 2001)'
_computing_data_reduction        'SAINT (Bruker, 2001'
_computing_molecular_graphics    'ORTEP-3 for Windows (Farrugia, 1997)'
_computing_publication_material  'WinGX (Farrugia, 1999)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      100.00(10)
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measurement_device_type  'Bruker SMART CCD area-detector'
_diffrn_measurement_method       'ω and φ'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0582
_diffrn_reflns_av_sigmaI/netI    0.0729
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       20
_diffrn_reflns_limit_k_min       -20
_diffrn_reflns_limit_l_max       29
_diffrn_reflns_limit_l_min       -29
_diffrn_reflns_number            22650
_diffrn_reflns_theta_full        25.03
_diffrn_reflns_theta_max         25.03
_diffrn_reflns_theta_min         1.67
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.278
_exptl_absorpt_correction_T_max  0.9732
_exptl_absorpt_correction_T_min  0.8948
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(SADABS; Bruker, 2001)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.748
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       plate
_exptl_crystal_F_000             1856
_exptl_crystal_size_max          0.4
_exptl_crystal_size_mid          0.36
_exptl_crystal_size_min          0.1
_refine_diff_density_max         0.285
_refine_diff_density_min         -0.280
_refine_ls_extinction_coef       0.00042(7)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     'SHELXL97 (Sheldrick, 2008)'
_refine_ls_goodness_of_fit_ref   0.804
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     281
_refine_ls_number_reflns         3098
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.804
_refine_ls_R_factor_all          0.0554
_refine_ls_R_factor_gt           0.0300
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w = 1/[σ²(Fo²)+(0.0222P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0509
_refine_ls_wR_factor_ref         0.0534
_reflns_number_gt                1888
_reflns_number_total             3098
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            xu2528.cif
_cod_data_source_block           I
_cod_database_code               2222499
_cod_database_fobs_code          2222499
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'
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 . .
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'
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_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_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
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 24742512
