#------------------------------------------------------------------------------ #$Date: 2016-02-20 00:18:51 +0200 (Sat, 20 Feb 2016) $ #$Revision: 176760 $ #$URL: file:///home/coder/svn-repositories/cod/cif/2/01/24/2012459.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_paper_doi 10.1107/S0108270101017632 _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 ? _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) _cod_data_source_file sk1518.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 The following automatic conversions were performed: '_exptl_crystal_density_meas' value 'not measured' was changed to '?' - the value is perceived as not measured. Automatic conversion script Id: cif_fix_values 3008 2015-01-20 13:52:24Z robertas ; _cod_original_sg_symbol_H-M 'P 21/c' _cod_database_code 2012459 _cod_database_fobs_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_disorder_assembly _atom_site_disorder_group _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_site_symmetry_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)