#------------------------------------------------------------------------------
#$Date: 2017-10-13 09:09:21 +0300 (Fri, 13 Oct 2017) $
#$Revision: 201973 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/20/70/2207029.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_2207029
loop_
_publ_author_name
'Ping-Hsin Huang'
'Yu-Da Cheng'
'Yuh-Sheng Wen'
'Ming-Chang P. Yeh'
'Jiann T. Lin'
_publ_section_title
;
 2,5-Bis(4-tert-butylphenyl)-3,4-dinitrothiophene
;
_journal_coeditor_code           OB6565
_journal_issue                   10
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o3168
_journal_page_last               o3169
_journal_paper_doi               10.1107/S1600536805026097
_journal_volume                  61
_journal_year                    2005
_chemical_formula_iupac          'C24 H26 N2 O4 S'
_chemical_formula_moiety         'C24 H26 N2 O4 S'
_chemical_formula_sum            'C24 H26 N2 O4 S'
_chemical_formula_weight         438.53
_chemical_name_systematic
;
2,5-Bis(4-tert-butylphenyl)-3,4-dinitrothiophene
;
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2ybc'
_symmetry_space_group_name_H-M   'P 1 21/c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                90.00
_cell_angle_beta                 99.349(9)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   14.026(3)
_cell_length_b                   11.120(2)
_cell_length_c                   14.491(3)
_cell_measurement_reflns_used    7514
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      31.21
_cell_measurement_theta_min      2.85
_cell_volume                     2230.1(8)
_computing_cell_refinement       'SAINT (Bruker, 2001)'
_computing_data_collection       'SMART (Bruker, 2001)'
_computing_data_reduction        SAINT
_computing_molecular_graphics    'ORTEP-3 for Windows (Farrugia, 1997)'
_computing_publication_material  'WinGX (Farrugia, 1999)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 1997)'
_diffrn_ambient_temperature      100(2)
_diffrn_measured_fraction_theta_full 0.995
_diffrn_measured_fraction_theta_max 0.995
_diffrn_measurement_device_type  'Bruker SMART CCD area-detector'
_diffrn_measurement_method       'φ and ω'
_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  0.0252
_diffrn_reflns_av_sigmaI/netI    0.0179
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            32280
_diffrn_reflns_theta_full        25.03
_diffrn_reflns_theta_max         25.03
_diffrn_reflns_theta_min         2.32
_exptl_absorpt_coefficient_mu    0.178
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.306
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             928
_exptl_crystal_size_max          0.32
_exptl_crystal_size_mid          0.24
_exptl_crystal_size_min          0.2
_refine_diff_density_max         0.222
_refine_diff_density_min         -0.234
_refine_ls_extinction_coef       0.0031(5)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     SHELXL97
_refine_ls_goodness_of_fit_ref   1.036
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     281
_refine_ls_number_reflns         3915
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.036
_refine_ls_R_factor_all          0.0341
_refine_ls_R_factor_gt           0.0302
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w = 1/[σ²(Fo²)+(0.0326P)²+1.2009P] where P = (Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0742
_refine_ls_wR_factor_ref         0.0772
_reflns_number_gt                3530
_reflns_number_total             3915
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            ob6565.cif
_cod_data_source_block           I
_cod_depositor_comments
;
The following automatic conversions were performed:
'_symmetry_cell_setting' value 'Monoclinic' changed to 'monoclinic'
according to '/home/saulius/struct/CIF-dictionaries/cif_core.dic'
dictionary named 'cif_core.dic' version 2.4.1 from 2010-06-29.

Automatic conversion script
Id: cif_fix_enum 1527 2010-12-29 10:47:43Z saulius 

The following automatic conversions were performed:

'_symmetry_cell_setting' value 'Monoclinic' changed to 'monoclinic'
according to /home/saulius/struct/CIF-dictionaries/cif_core.dic
dictionary named 'cif_core.dic' version 2.4.1 from 2010-06-29.

Automatic conversion script
Id: cif_fix_values 1715 2011-07-08 13:25:40Z adriana 
;
_cod_original_cell_volume        2230.2(8)
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               2207029
_cod_database_fobs_code          2207029
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'
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_type_symbol
S 0.14983(2) 0.08831(3) 0.58157(2) 0.01804(11) Uani d . 1 S
O1 0.31389(7) -0.06073(10) 0.36082(7) 0.0294(3) Uani d . 1 O
O2 0.16866(8) -0.06315(10) 0.28221(7) 0.0295(3) Uani d . 1 O
O3 0.11336(8) 0.18529(11) 0.26159(7) 0.0332(3) Uani d . 1 O
O4 -0.02213(8) 0.10858(11) 0.28763(8) 0.0349(3) Uani d . 1 O
N3 0.22802(8) -0.03514(10) 0.35079(8) 0.0201(3) Uani d . 1 N
N4 0.06309(9) 0.13440(11) 0.31079(8) 0.0225(3) Uani d . 1 N
C2 0.22356(9) 0.01059(12) 0.51825(9) 0.0168(3) Uani d . 1 C
C3 0.19237(10) 0.03018(12) 0.42469(9) 0.0175(3) Uani d . 1 C
C4 0.10854(10) 0.10342(12) 0.40599(9) 0.0181(3) Uani d . 1 C
C5 0.07559(9) 0.14406(12) 0.48364(9) 0.0182(3) Uani d . 1 C
C11 0.30055(10) -0.06503(12) 0.57029(9) 0.0166(3) Uani d . 1 C
C12 0.39619(10) -0.05294(13) 0.55743(10) 0.0204(3) Uani d . 1 C
H12 0.4119 0.0004 0.5110 0.024 Uiso calc R 1 H
C13 0.46855(10) -0.11787(13) 0.61171(10) 0.0205(3) Uani d . 1 C
H13 0.5334 -0.1080 0.6017 0.025 Uiso calc R 1 H
C14 0.44934(9) -0.19708(12) 0.68036(9) 0.0169(3) Uani d . 1 C
C15 0.35282(10) -0.21019(12) 0.69175(9) 0.0186(3) Uani d . 1 C
H15 0.3371 -0.2651 0.7372 0.022 Uiso calc R 1 H
C16 0.27962(10) -0.14511(12) 0.63845(9) 0.0180(3) Uani d . 1 C
H16 0.2148 -0.1550 0.6483 0.022 Uiso calc R 1 H
C17 0.52959(10) -0.26877(12) 0.74022(10) 0.0194(3) Uani d . 1 C
C18 0.63043(10) -0.22355(14) 0.72934(11) 0.0250(3) Uani d . 1 C
H18A 0.6384 -0.2290 0.6635 0.037 Uiso calc R 1 H
H18B 0.6796 -0.2731 0.7675 0.037 Uiso calc R 1 H
H18C 0.6377 -0.1397 0.7500 0.037 Uiso calc R 1 H
C19 0.52019(10) -0.25867(13) 0.84402(10) 0.0234(3) Uani d . 1 C
H19A 0.5721 -0.3047 0.8817 0.035 Uiso calc R 1 H
H19B 0.4574 -0.2908 0.8535 0.035 Uiso calc R 1 H
H19C 0.5251 -0.1740 0.8631 0.035 Uiso calc R 1 H
C20 0.52005(11) -0.40104(13) 0.70881(11) 0.0253(3) Uani d . 1 C
H20A 0.5259 -0.4066 0.6425 0.038 Uiso calc R 1 H
H20B 0.4569 -0.4321 0.7180 0.038 Uiso calc R 1 H
H20C 0.5713 -0.4487 0.7459 0.038 Uiso calc R 1 H
C21 -0.00364(10) 0.22648(12) 0.49495(10) 0.0183(3) Uani d . 1 C
C22 -0.05037(10) 0.21570(13) 0.57232(9) 0.0190(3) Uani d . 1 C
H22 -0.0314 0.1541 0.6170 0.023 Uiso calc R 1 H
C23 -0.12390(10) 0.29344(12) 0.58488(10) 0.0193(3) Uani d . 1 C
H23 -0.1550 0.2838 0.6379 0.023 Uiso calc R 1 H
C24 -0.15370(10) 0.38585(12) 0.52166(10) 0.0191(3) Uani d . 1 C
C25 -0.10578(10) 0.39718(13) 0.44527(10) 0.0227(3) Uani d . 1 C
H25 -0.1238 0.4599 0.4014 0.027 Uiso calc R 1 H
C26 -0.03232(10) 0.31915(13) 0.43164(10) 0.0226(3) Uani d . 1 C
H26 -0.0012 0.3289 0.3786 0.027 Uiso calc R 1 H
C27 -0.23583(10) 0.46944(13) 0.53889(10) 0.0238(3) Uani d . 1 C
C28 -0.20964(12) 0.52867(15) 0.63508(12) 0.0339(4) Uani d . 1 C
H28A -0.2623 0.5819 0.6462 0.051 Uiso calc R 1 H
H28B -0.1502 0.5757 0.6371 0.051 Uiso calc R 1 H
H28C -0.1996 0.4664 0.6835 0.051 Uiso calc R 1 H
C29 -0.32802(11) 0.39450(15) 0.53742(12) 0.0309(4) Uani d . 1 C
H29A -0.3812 0.4472 0.5481 0.046 Uiso calc R 1 H
H29B -0.3170 0.3334 0.5867 0.046 Uiso calc R 1 H
H29C -0.3448 0.3550 0.4765 0.046 Uiso calc R 1 H
C30 -0.25536(13) 0.56730(17) 0.46464(14) 0.0432(5) Uani d . 1 C
H30A -0.3085 0.6184 0.4776 0.065 Uiso calc R 1 H
H30B -0.2729 0.5301 0.4029 0.065 Uiso calc R 1 H
H30C -0.1971 0.6163 0.4656 0.065 Uiso calc R 1 H
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'
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
_geom_angle_publ_flag
C2 S C5 94.37(7) yes
O1 N3 O2 124.20(12) ?
O1 N3 C3 118.70(11) ?
O2 N3 C3 117.08(12) ?
O3 N4 O4 125.50(12) ?
O3 N4 C4 117.09(12) ?
O4 N4 C4 117.40(12) ?
C3 C2 C11 133.20(12) ?
C3 C2 S 108.90(10) yes
C11 C2 S 117.81(10) ?
C2 C3 C4 113.62(12) yes
C2 C3 N3 123.90(12) ?
C4 C3 N3 121.41(12) ?
C5 C4 C3 114.49(12) yes
C5 C4 N4 123.14(12) ?
C3 C4 N4 122.36(12) ?
C4 C5 C21 131.57(13) ?
C4 C5 S 108.58(10) ?
C21 C5 S 119.75(10) ?
C12 C11 C16 118.34(12) ?
C12 C11 C2 121.22(12) ?
C16 C11 C2 120.30(12) ?
C13 C12 C11 120.56(13) ?
C13 C12 H12 119.7 ?
C11 C12 H12 119.7 ?
C12 C13 C14 121.97(13) ?
C12 C13 H13 119.0 ?
C14 C13 H13 119.0 ?
C13 C14 C15 117.10(12) ?
C13 C14 C17 121.80(12) ?
C15 C14 C17 121.09(12) ?
C16 C15 C14 121.62(13) ?
C16 C15 H15 119.2 ?
C14 C15 H15 119.2 ?
C15 C16 C11 120.40(12) ?
C15 C16 H16 119.8 ?
C11 C16 H16 119.8 ?
C14 C17 C18 112.15(12) ?
C14 C17 C19 110.20(11) ?
C18 C17 C19 107.71(12) ?
C14 C17 C20 108.06(11) ?
C18 C17 C20 108.68(12) ?
C19 C17 C20 110.03(12) ?
C17 C18 H18A 109.5 ?
C17 C18 H18B 109.5 ?
H18A C18 H18B 109.5 ?
C17 C18 H18C 109.5 ?
H18A C18 H18C 109.5 ?
H18B C18 H18C 109.5 ?
C17 C19 H19A 109.5 ?
C17 C19 H19B 109.5 ?
H19A C19 H19B 109.5 ?
C17 C19 H19C 109.5 ?
H19A C19 H19C 109.5 ?
H19B C19 H19C 109.5 ?
C17 C20 H20A 109.5 ?
C17 C20 H20B 109.5 ?
H20A C20 H20B 109.5 ?
C17 C20 H20C 109.5 ?
H20A C20 H20C 109.5 ?
H20B C20 H20C 109.5 ?
C22 C21 C26 118.03(13) ?
C22 C21 C5 119.95(12) ?
C26 C21 C5 121.99(13) ?
C23 C22 C21 120.77(13) ?
C23 C22 H22 119.6 ?
C21 C22 H22 119.6 ?
C22 C23 C24 121.70(13) ?
C22 C23 H23 119.1 ?
C24 C23 H23 119.1 ?
C25 C24 C23 117.22(13) ?
C25 C24 C27 123.24(13) ?
C23 C24 C27 119.54(13) ?
C26 C25 C24 121.56(13) ?
C26 C25 H25 119.2 ?
C24 C25 H25 119.2 ?
C25 C26 C21 120.70(13) ?
C25 C26 H26 119.6 ?
C21 C26 H26 119.6 ?
C30 C27 C28 108.95(14) ?
C30 C27 C24 111.84(12) ?
C28 C27 C24 109.50(12) ?
C30 C27 C29 108.87(13) ?
C28 C27 C29 108.84(13) ?
C24 C27 C29 108.79(12) ?
C27 C28 H28A 109.5 ?
C27 C28 H28B 109.5 ?
H28A C28 H28B 109.5 ?
C27 C28 H28C 109.5 ?
H28A C28 H28C 109.5 ?
H28B C28 H28C 109.5 ?
C27 C29 H29A 109.5 ?
C27 C29 H29B 109.5 ?
H29A C29 H29B 109.5 ?
C27 C29 H29C 109.5 ?
H29A C29 H29C 109.5 ?
H29B C29 H29C 109.5 ?
C27 C30 H30A 109.5 ?
C27 C30 H30B 109.5 ?
H30A C30 H30B 109.5 ?
C27 C30 H30C 109.5 ?
H30A C30 H30C 109.5 ?
H30B C30 H30C 109.5 ?
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_publ_flag
S C2 1.7224(14) yes
S C5 1.7327(14) yes
O1 N3 1.2231(15) ?
O2 N3 1.2284(15) ?
O3 N4 1.2202(16) ?
O4 N4 1.2220(16) ?
N3 C3 1.4486(18) ?
N4 C4 1.4638(18) ?
C2 C3 1.3727(19) yes
C2 C11 1.4755(19) ?
C3 C4 1.4198(19) yes
C4 C5 1.361(2) yes
C5 C21 1.4699(19) ?
C11 C12 1.391(2) ?
C11 C16 1.3961(19) ?
C12 C13 1.382(2) ?
C12 H12 0.9500 ?
C13 C14 1.3875(19) ?
C13 H13 0.9500 ?
C14 C15 1.3977(19) ?
C14 C17 1.5290(19) ?
C15 C16 1.3844(19) ?
C15 H15 0.9500 ?
C16 H16 0.9500 ?
C17 C18 1.5333(19) ?
C17 C19 1.535(2) ?
C17 C20 1.539(2) ?
C18 H18A 0.9800 ?
C18 H18B 0.9800 ?
C18 H18C 0.9800 ?
C19 H19A 0.9800 ?
C19 H19B 0.9800 ?
C19 H19C 0.9800 ?
C20 H20A 0.9800 ?
C20 H20B 0.9800 ?
C20 H20C 0.9800 ?
C21 C22 1.393(2) ?
C21 C26 1.395(2) ?
C22 C23 1.380(2) ?
C22 H22 0.9500 ?
C23 C24 1.395(2) ?
C23 H23 0.9500 ?
C24 C25 1.391(2) ?
C24 C27 1.5319(19) ?
C25 C26 1.385(2) ?
C25 H25 0.9500 ?
C26 H26 0.9500 ?
C27 C30 1.524(2) ?
C27 C28 1.531(2) ?
C27 C29 1.536(2) ?
C28 H28A 0.9800 ?
C28 H28B 0.9800 ?
C28 H28C 0.9800 ?
C29 H29A 0.9800 ?
C29 H29B 0.9800 ?
C29 H29C 0.9800 ?
C30 H30A 0.9800 ?
C30 H30B 0.9800 ?
C30 H30C 0.9800 ?
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 21128754
