#------------------------------------------------------------------------------ #$Date: 2011-09-10 06:16:28 +0300 (Sat, 10 Sep 2011) $ #$Revision: 25271 $ #$URL: file:///home/coder/svn-repositories/cod/cif/2/2012459.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_2012459 loop_ _publ_author_name 'Crean, Colm' 'Gallagher, John F.' 'Pratt, Albert C.' _publ_section_title ; 2,2'-[2,3-Dihydro-2-(prop-2-enyl)-1H-isoindole-1,3-diylidene]bis(propanedinitrile)--tetrathiafulvalene (1/1), TCPI--TTF ; _journal_issue 1 _journal_name_full 'Acta Crystallographica Section C' _journal_page_first o36 _journal_page_last o38 _journal_volume 58 _journal_year 2002 _chemical_formula_moiety 'C17 H9 N5, C6 H4 S4' _chemical_formula_sum 'C23 H13 N5 S4' _chemical_formula_weight 487.62 _chemical_melting_point 443 _chemical_name_common TCPI-TTF _chemical_name_systematic ; 2-[3-(1-cyano-2-nitriloethylidene)-2-prop-2-enyl-2,3-dihydro- 1H-isoindol-1-yliden]propanedinitrile tetrathiafulvalene (1:1) ; _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 _cell_angle_alpha 90 _cell_angle_beta 94.608(17) _cell_angle_gamma 90 _cell_formula_units_Z 4 _cell_length_a 7.3982(11) _cell_length_b 31.854(5) _cell_length_c 9.516(2) _cell_measurement_reflns_used 25 _cell_measurement_temperature 294.0(10) _cell_measurement_theta_max 19.9 _cell_measurement_theta_min 5.5 _cell_volume 2235.3(7) _computing_cell_refinement 'XSCANS ' _computing_data_collection 'XSCANS (Siemens, 1994)' _computing_data_reduction 'XSCANS ' _computing_molecular_graphics 'ORTEPIII (Burnett & Johnson, 1996), PLATON (Spek, 1998)' _computing_publication_material 'SHELXL97 and WordPerfect macro PREP8 (Ferguson, 1998)' _computing_structure_refinement 'SHELXL97 (Sheldrick, 1997)' _computing_structure_solution 'SHELXS97 (Sheldrick, 1997)' _diffrn_ambient_temperature 296(2) _diffrn_measured_fraction_theta_full .99 _diffrn_measured_fraction_theta_max .99 _diffrn_measurement_device 'Bruker AXS P4 diffractometer' _diffrn_measurement_method \w _diffrn_radiation_monochromator graphite _diffrn_radiation_source 'X-ray tube' _diffrn_radiation_type 'Molybdenum K\a' _diffrn_radiation_wavelength .71073 _diffrn_reflns_av_R_equivalents .018 _diffrn_reflns_av_sigmaI/netI .021 _diffrn_reflns_limit_h_max 9 _diffrn_reflns_limit_h_min -1 _diffrn_reflns_limit_k_max 1 _diffrn_reflns_limit_k_min -42 _diffrn_reflns_limit_l_max 12 _diffrn_reflns_limit_l_min -12 _diffrn_reflns_number 5764 _diffrn_reflns_theta_full 28.00 _diffrn_reflns_theta_max 28.0 _diffrn_reflns_theta_min 2.2 _diffrn_standards_decay_% 1 _diffrn_standards_interval_count 296 _diffrn_standards_number 3 _exptl_absorpt_coefficient_mu .447 _exptl_absorpt_correction_T_max .860 _exptl_absorpt_correction_T_min .806 _exptl_absorpt_correction_type psi-scan _exptl_absorpt_process_details '(North et al., 1968)' _exptl_crystal_colour red _exptl_crystal_density_diffrn 1.449 _exptl_crystal_density_meas 'not measured' _exptl_crystal_description block _exptl_crystal_F_000 1000 _exptl_crystal_size_max .50 _exptl_crystal_size_mid .50 _exptl_crystal_size_min .35 _refine_diff_density_max .71 _refine_diff_density_min -.38 _refine_ls_extinction_method none _refine_ls_goodness_of_fit_ref 1.09 _refine_ls_hydrogen_treatment constr _refine_ls_matrix_type full _refine_ls_number_parameters 289 _refine_ls_number_reflns 5366 _refine_ls_number_restraints 0 _refine_ls_restrained_S_all 1.09 _refine_ls_R_factor_all .060 _refine_ls_R_factor_gt .045 _refine_ls_shift/su_max .001 _refine_ls_shift/su_mean .000 _refine_ls_structure_factor_coef Fsqd _refine_ls_weighting_details 'w=1/[\s^2^(Fo^2^)+(0.0586P)^2^+0.6527P] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_gt .110 _refine_ls_wR_factor_ref .121 _reflns_number_gt 4247 _reflns_number_total 5366 _reflns_threshold_expression I>2\s(I) _[local]_cod_data_source_file sk1518.cif _[local]_cod_data_source_block I _[local]_cod_cif_authors_sg_H-M P21/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_values 1715 2011-07-08 13:25:40Z adriana ; _cod_database_code 2012459 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 S1 .42240(8) .311005(18) .43274(6) .05158(15) Uani d . 1 S S2 .29873(8) .397780(17) .36781(6) .04844(14) Uani d . 1 S S3 .20999(8) .372260(17) .04086(6) .05053(15) Uani d . 1 S S4 .33541(9) .285452(17) .10331(6) .05370(16) Uani d . 1 S C1T .3349(3) .34667(6) .3047(2) .0406(4) Uani d . 1 C C2T .2992(3) .33626(6) .1685(2) .0412(4) Uani d . 1 C C3T .3757(4) .38603(9) .5401(2) .0626(6) Uani d . 1 C C4T .4310(4) .34756(9) .5689(2) .0634(6) Uani d . 1 C C5T .2666(4) .29802(9) -.0692(3) .0635(6) Uani d . 1 C C6T .2110(4) .33689(9) -.0971(2) .0625(6) Uani d . 1 C N1 -.2780(2) .41884(5) .25033(16) .0370(3) Uani d . 1 N N2A -.0196(3) .41153(7) .7339(2) .0666(6) Uani d . 1 N N3A -.2593(4) .51313(7) .5137(3) .0823(8) Uani d . 1 N N2B -.2645(4) .32291(7) -.1453(2) .0711(6) Uani d . 1 N N3B -.4189(3) .44801(8) -.1456(2) .0729(6) Uani d . 1 N C1 -.3455(3) .46094(6) .2103(2) .0440(4) Uani d . 1 C C2 -.1977(3) .48993(7) .1729(2) .0552(6) Uani d . 1 C C3 -.0272(4) .48082(8) .1703(3) .0601(6) Uani d . 1 C C4 -.2067(2) .40810(6) .38449(19) .0361(4) Uani d . 1 C C5 -.2669(2) .38570(6) .15770(19) .0359(4) Uani d . 1 C C11 -.1602(2) .36343(5) .3808(2) .0359(4) Uani d . 1 C C12 -.0962(3) .33577(6) .4859(2) .0446(4) Uani d . 1 C C13 -.0705(3) .29412(7) .4495(2) .0512(5) Uani d . 1 C C14 -.1085(3) .28042(6) .3131(2) .0513(5) Uani d . 1 C C15 -.1727(3) .30756(6) .2067(2) .0460(4) Uani d . 1 C C16 -.1979(2) .34963(6) .24217(19) .0360(4) Uani d . 1 C C6A -.1806(3) .43472(6) .4976(2) .0420(4) Uani d . 1 C C7A -.0920(3) .42079(6) .6283(2) .0480(5) Uani d . 1 C C8A -.2266(3) .47860(7) .5015(2) .0541(5) Uani d . 1 C C6B -.3069(3) .38675(6) .0142(2) .0419(4) Uani d . 1 C C7B -.2814(3) .35038(7) -.0704(2) .0494(5) Uani d . 1 C C8B -.3692(3) .42203(7) -.0695(2) .0505(5) Uani d . 1 C H3T .3779 .4064 .6102 .075 Uiso calc R 1 H H4T .4737 .3400 .6600 .076 Uiso calc R 1 H H5T .2685 .2781 -.1405 .076 Uiso calc R 1 H H6T .1734 .3450 -.1887 .075 Uiso calc R 1 H H1A -.4053 .4729 .2881 .053 Uiso calc R 1 H H1B -.4348 .4585 .1303 .053 Uiso calc R 1 H H2 -.2316 .5173 .1489 .066 Uiso calc R 1 H H3A .0136 .4539 .1934 .072 Uiso calc R 1 H H3B .0543 .5012 .1455 .072 Uiso calc R 1 H H12 -.0712 .3449 .5783 .054 Uiso calc R 1 H H13 -.0269 .2752 .5184 .061 Uiso calc R 1 H H14 -.0907 .2523 .2919 .062 Uiso calc R 1 H H15 -.1981 .2981 .1147 .055 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 S1 .0551(3) .0500(3) .0493(3) .0000(2) .0016(2) .0095(2) S2 .0518(3) .0415(3) .0527(3) -.0018(2) .0085(2) -.0052(2) S3 .0547(3) .0452(3) .0513(3) .0057(2) .0021(2) .0079(2) S4 .0721(4) .0400(3) .0484(3) .0047(2) .0012(3) -.0020(2) C1T .0390(10) .0382(9) .0450(10) -.0031(8) .0059(8) .0006(8) C2T .0436(10) .0367(9) .0434(10) -.0014(8) .0044(8) .0026(8) C3T .0694(16) .0723(16) .0463(12) -.0032(13) .0066(11) -.0135(11) C4T .0669(15) .0818(18) .0405(11) -.0003(13) -.0004(10) .0024(11) C5T .0734(16) .0682(15) .0469(12) .0133(13) -.0070(11) -.0110(11) C6T .0700(16) .0729(16) .0431(11) .0134(13) -.0048(11) .0012(11) N1 .0401(8) .0311(7) .0397(8) .0051(6) .0037(6) .0051(6) N2A .0947(16) .0528(11) .0506(11) .0065(11) -.0055(11) .0038(9) N3A .130(2) .0469(12) .0673(14) .0220(13) -.0099(14) -.0118(10) N2B .1015(18) .0563(12) .0536(11) .0069(12) -.0058(11) -.0079(10) N3B .0888(16) .0725(14) .0569(12) .0256(12) .0023(11) .0176(11) C1 .0511(11) .0344(9) .0459(10) .0114(8) .0012(8) .0056(8) C2 .0728(16) .0344(10) .0583(13) .0024(10) .0037(11) .0131(9) C3 .0676(15) .0532(13) .0605(14) -.0105(12) .0118(11) .0106(11) C4 .0353(9) .0334(9) .0401(9) .0011(7) .0068(7) .0066(7) C5 .0315(9) .0337(8) .0429(9) .0014(7) .0056(7) .0037(7) C11 .0339(9) .0301(8) .0442(9) -.0001(7) .0058(7) .0055(7) C12 .0502(11) .0375(10) .0456(10) .0014(8) .0003(9) .0073(8) C13 .0572(13) .0381(10) .0574(12) .0048(9) -.0001(10) .0140(9) C14 .0610(13) .0309(9) .0623(13) .0061(9) .0068(10) .0048(9) C15 .0545(12) .0340(9) .0494(11) .0030(8) .0040(9) .0021(8) C16 .0340(9) .0315(8) .0427(9) -.0001(7) .0045(7) .0052(7) C6A .0479(11) .0362(9) .0423(9) .0039(8) .0060(8) .0034(7) C7A .0618(13) .0379(10) .0448(10) .0017(9) .0066(9) .0009(8) C8A .0726(15) .0431(11) .0459(11) .0082(10) .0012(10) -.0041(9) C6B .0412(10) .0419(10) .0424(10) .0016(8) .0029(8) .0038(8) C7B .0552(12) .0482(11) .0437(10) .0022(9) -.0028(9) .0032(9) C8B .0533(12) .0543(12) .0439(10) .0095(10) .0037(9) .0059(9) loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C .0033 .0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H .0000 .0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N .0061 .0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' S S .1246 .1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' loop_ _diffrn_standard_refln_index_h _diffrn_standard_refln_index_k _diffrn_standard_refln_index_l 0 16 0 -2 5 1 0 0 2 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 S1 C1T S2 114.83(11) ? S3 C2T S4 114.51(11) ? C1T S1 C4T 94.21(11) ? C1T S2 C3T 94.32(11) ? C2T S3 C6T 94.30(11) ? C2T S4 C5T 94.60(11) ? C2T C1T S1 122.97(16) ? C2T C1T S2 122.20(16) ? C1T C2T S3 122.61(16) ? C1T C2T S4 122.88(15) ? C3T C4T S1 118.46(19) ? C4T C3T S2 118.18(19) ? C5T C6T S3 118.47(19) ? C6T C5T S4 118.06(19) ? S1 C4T H4T 120.8 ? S2 C3T H3T 120.9 ? S3 C6T H6T 120.8 ? S4 C5T H5T 121.0 ? C3T C4T H4T 120.8 ? C4T C3T H3T 120.9 ? C5T C6T H6T 120.8 ? C6T C5T H5T 121.0 ? C1 N1 C4 124.08(16) ? C1 N1 C5 124.61(16) ? C4 N1 C5 111.20(15) ? N1 C1 C2 112.65(17) yes C1 C2 C3 126.6(2) yes C6A C4 N1 126.14(17) ? C6A C4 C11 126.93(17) ? N1 C4 C11 106.91(16) ? C6B C5 N1 126.59(17) ? C6B C5 C16 126.88(17) ? N1 C5 C16 106.51(15) ? C12 C11 C4 131.83(18) ? C16 C11 C4 107.37(15) ? C12 C11 C16 120.77(17) ? C11 C12 C13 118.20(19) ? C12 C13 C14 121.12(19) ? C13 C14 C15 121.54(19) ? C14 C15 C16 117.8(2) ? C11 C16 C15 120.62(17) ? C11 C16 C5 107.74(16) ? C15 C16 C5 131.62(18) ? C4 C6A C7A 121.10(17) ? C4 C6A C8A 127.01(18) ? C5 C6B C7B 120.75(18) ? C5 C6B C8B 127.29(19) ? N2A C7A C6A 176.9(2) ? N3A C8A C6A 175.5(3) ? N2B C7B C6B 175.6(2) ? N3B C8B C6B 174.3(3) ? C7A C6A C8A 111.82(18) ? C7B C6B C8B 111.92(18) ? N1 C1 H1A 109.1 ? C2 C1 H1A 109.1 ? N1 C1 H1B 109.1 ? C2 C1 H1B 109.1 ? C3 C2 H2 116.7 ? C1 C2 H2 116.7 ? C2 C3 H3A 120.0 ? C2 C3 H3B 120.0 ? H3A C3 H3B 120.0 ? H1A C1 H1B 107.8 ? C11 C12 H12 120.9 ? C13 C12 H12 120.9 ? C14 C13 H13 119.4 ? C12 C13 H13 119.4 ? C13 C14 H14 119.2 ? C15 C14 H14 119.2 ? C14 C15 H15 121.1 ? C16 C15 H15 121.1 ? loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_publ_flag S1 C1T 1.751(2) yes S1 C4T 1.740(3) yes S2 C1T 1.763(2) yes S2 C3T 1.733(3) yes S3 C2T 1.760(2) yes S3 C6T 1.731(3) yes S4 C2T 1.761(2) yes S4 C5T 1.726(3) yes C1T C2T 1.344(3) yes C3T C4T 1.314(4) yes C5T C6T 1.325(4) yes N1 C1 1.471(2) yes N1 C4 1.385(2) yes N1 C5 1.382(2) yes N2A C7A 1.139(3) no N3A C8A 1.134(3) no N2B C7B 1.142(3) no N3B C8B 1.141(3) no C1 C2 1.496(3) yes C2 C3 1.296(3) yes C4 C6A 1.372(3) no C4 C11 1.465(2) no C5 C6B 1.374(3) no C5 C16 1.470(2) no C6A C7A 1.430(3) no C6A C8A 1.440(3) no C6B C7B 1.432(3) no C6B C8B 1.432(3) no C11 C12 1.387(3) no C11 C16 1.398(3) no C12 C13 1.388(3) no C13 C14 1.377(3) no C14 C15 1.387(3) no C15 C16 1.398(3) no C3T H3T .9300 no C4T H4T .9300 no C5T H5T .9300 no C6T H6T .9300 no C1 H1A .9700 no C1 H1B .9700 no C2 H2 .9300 no C3 H3A .9300 no C3 H3B .9300 no C12 H12 .9300 no C13 H13 .9300 no C14 H14 .9300 no C15 H15 .9300 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 C12 H12 N2A 1_555 .93 2.60 3.391(3) 143 yes C12 H12 C7A 1_555 .93 2.47 3.027(3) 118 yes C15 H15 N2B 1_555 .93 2.61 3.399(3) 144 yes C15 H15 C7B 1_555 .93 2.47 3.020(3) 118 yes C4T H4T N2B 1_656 .93 2.63 3.479(3) 152 yes C6T H6T N2A 1_554 .93 2.63 3.273(3) 127 yes 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 S1 C1T C2T S3 179.61(11) S2 C1T C2T S3 -1.0(3) S1 C1T C2T S4 .3(3) S2 C1T C2T S4 179.70(11) S2 C3T C4T S1 -.2(3) S4 C5T C6T S3 -.3(3) C3T S2 C1T S1 .27(14) C4T S1 C1T S2 -.36(14) C5T S4 C2T S3 2.12(15) C6T S3 C2T S4 -2.24(15) C4T S1 C1T C2T 179.11(19) C3T S2 C1T C2T -179.21(19) C6T S3 C2T C1T 178.37(19) C5T S4 C2T C1T -178.5(2) C1T S2 C3T C4T .0(2) C1T S1 C4T C3T .4(2) C2T S4 C5T C6T -1.1(3) C2T S3 C6T C5T 1.6(3) C4 N1 C1 C2 84.3(2) C5 N1 C1 C2 -91.4(2) N1 C1 C2 C3 1.6(3) C1 N1 C4 C6A -3.0(3) C5 N1 C4 C6A 173.26(18) C1 N1 C4 C11 178.58(16) C5 N1 C4 C11 -5.2(2) C1 N1 C5 C6B 3.6(3) C4 N1 C5 C6B -172.65(18) C1 N1 C5 C16 -178.33(17) C4 N1 C5 C16 5.4(2) C6A C4 C11 C12 6.5(3) N1 C4 C11 C12 -175.1(2) C6A C4 C11 C16 -175.68(18) N1 C4 C11 C16 2.7(2) C16 C11 C12 C13 .1(3) C4 C11 C12 C13 177.7(2) C11 C12 C13 C14 -.4(3) C12 C13 C14 C15 .4(4) C13 C14 C15 C16 .0(3) C12 C11 C16 C15 .3(3) C4 C11 C16 C15 -177.86(17) C12 C11 C16 C5 178.64(17) C4 C11 C16 C5 .5(2) C14 C15 C16 C11 -.3(3) C14 C15 C16 C5 -178.2(2) C6B C5 C16 C11 174.54(18) N1 C5 C16 C11 -3.5(2) C6B C5 C16 C15 -7.4(3) N1 C5 C16 C15 174.6(2) N1 C4 C6A C7A -174.86(18) C11 C4 C6A C7A 3.3(3) N1 C4 C6A C8A 2.0(3) C11 C4 C6A C8A -179.8(2) N1 C5 C6B C7B 177.14(19) C16 C5 C6B C7B -.6(3) N1 C5 C6B C8B -.4(3) C16 C5 C6B C8B -178.1(2)