#------------------------------------------------------------------------------ #$Date: 2013-08-29 16:37:19 +0100 (Thu, 29 Aug 2013) $ #$Revision: 88064 $ #$URL: svn://www.crystallography.net/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_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 '\f and \w' _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+0.001xFc^2^\l^3^/sin(2\q)]^-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/[\s^2^(Fo^2^)+(0.0326P)^2^+1.2009P] where P = (Fo^2^+2Fc^2^)/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>2\s(I) _[local]_cod_data_source_file ob6565.cif _[local]_cod_data_source_block I _[local]_cod_cif_authors_sg_H-M 'P 21/c' _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_database_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_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 S 0.01659(18) 0.02116(19) 0.01617(19) 0.00389(13) 0.00204(13) -0.00043(13) O1 0.0225(6) 0.0372(6) 0.0295(6) 0.0079(5) 0.0074(4) -0.0052(5) O2 0.0324(6) 0.0372(6) 0.0176(5) 0.0020(5) 0.0000(5) -0.0055(5) O3 0.0313(6) 0.0436(7) 0.0252(6) -0.0008(5) 0.0060(5) 0.0131(5) O4 0.0216(6) 0.0542(8) 0.0260(6) -0.0051(5) -0.0051(4) 0.0026(5) N3 0.0241(7) 0.0192(6) 0.0175(6) 0.0010(5) 0.0044(5) 0.0015(5) N4 0.0222(6) 0.0253(7) 0.0196(6) 0.0026(5) 0.0015(5) 0.0018(5) C2 0.0157(7) 0.0156(7) 0.0195(7) -0.0016(5) 0.0042(5) -0.0013(5) C3 0.0172(7) 0.0173(7) 0.0185(7) -0.0006(5) 0.0043(5) -0.0012(6) C4 0.0165(7) 0.0199(7) 0.0171(7) -0.0008(5) 0.0007(5) 0.0015(6) C5 0.0155(7) 0.0188(7) 0.0196(7) -0.0014(5) 0.0012(5) 0.0012(6) C11 0.0176(7) 0.0156(7) 0.0161(7) 0.0006(5) 0.0013(5) -0.0028(5) C12 0.0203(7) 0.0212(7) 0.0206(7) -0.0003(6) 0.0061(6) 0.0040(6) C13 0.0151(7) 0.0234(8) 0.0240(8) 0.0006(6) 0.0060(6) 0.0024(6) C14 0.0181(7) 0.0137(7) 0.0188(7) 0.0009(5) 0.0030(5) -0.0022(5) C15 0.0211(7) 0.0162(7) 0.0188(7) -0.0019(6) 0.0048(5) 0.0017(5) C16 0.0157(7) 0.0189(7) 0.0202(7) -0.0006(5) 0.0049(5) -0.0010(6) C17 0.0179(7) 0.0170(7) 0.0230(7) 0.0020(6) 0.0027(6) 0.0018(6) C18 0.0182(7) 0.0263(8) 0.0300(8) 0.0051(6) 0.0028(6) 0.0043(7) C19 0.0219(7) 0.0241(8) 0.0233(8) 0.0032(6) 0.0008(6) 0.0020(6) C20 0.0282(8) 0.0177(7) 0.0291(8) 0.0051(6) 0.0024(6) 0.0010(6) C21 0.0139(6) 0.0202(7) 0.0202(7) -0.0004(5) 0.0008(5) -0.0016(6) C22 0.0187(7) 0.0192(7) 0.0179(7) 0.0001(6) -0.0002(5) 0.0006(6) C23 0.0183(7) 0.0215(7) 0.0181(7) -0.0006(6) 0.0034(5) -0.0023(6) C24 0.0150(7) 0.0192(7) 0.0219(7) -0.0007(5) -0.0004(5) -0.0032(6) C25 0.0205(7) 0.0230(8) 0.0237(8) 0.0030(6) 0.0010(6) 0.0038(6) C26 0.0196(7) 0.0270(8) 0.0218(7) 0.0013(6) 0.0054(6) 0.0038(6) C27 0.0196(7) 0.0232(8) 0.0283(8) 0.0047(6) 0.0029(6) -0.0013(6) C28 0.0268(8) 0.0309(9) 0.0433(10) 0.0054(7) 0.0034(7) -0.0144(8) C29 0.0182(8) 0.0359(9) 0.0385(9) 0.0037(7) 0.0037(7) -0.0102(7) C30 0.0404(10) 0.0411(10) 0.0514(12) 0.0241(8) 0.0170(9) 0.0162(9) 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 ? _cod_database_fobs_code 2207029