Supplementary Material (ESI) for Journal of Materials Chemistry This journal is © The Royal Society of Chemistry 2001 data_global _journal_coden_Cambridge 1145 _publ_contact_author 'Prof M Bryce' _publ_contact_author_address ; Department of Chemistry University of Durham South Road DURHAM DH1 3LE UK ; _publ_contact_author_email 'M.R.BRYCE@DURHAM.AC.UK' loop_ _publ_author_name 'Batsanov, Andrei S.' 'Bryce, Martin R.' 'Chesney, Antony' 'Howard, Judith A. K.' 'John, Derek E.' 'Moore, Adrian J.' 'Wood, Clare L.' 'Gershtenman, Hargit' 'Becker, James Y.' 'Khodorkovsky, Vladimir Y.' 'Ellern, Arkady' 'Bernstein, Joel' 'Perepichka, Igor F.' 'Rotello, Vincent' 'Gray, Mark' 'Cuello, Alejandro O.' _journal_name_full 'Journal of Materials Chemistry' _journal_volume '?' _journal_page_first '?' _journal_page_last '?' _journal_year '2001' _publ_section_title ; Synthesis and crystal engineering of new halogenated tetathiafulvalene (TTF) derivatives and their charge transfer complexes nd radical ion salts ; #====================================================================== data_2 _database_code_CSD 161754 _audit_creation_method SHELXL _chemical_name_systematic ; 4,4',5,5'-tetraiodotetrathiafulvalene ; _chemical_name_common ? _chemical_formula_moiety ? _chemical_formula_sum 'C6 I4 S4' _chemical_formula_weight 707.90 _chemical_melting_point '203\% C' _chemical_compound_source ? _ccdc_compound_id '2' _ccdc_biological_activity '?' _ccdc_polymorph '?' _ccdc_disorder 'none' _ccdc_comments '?' loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source 'C' 'C' 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 'S' 'S' 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 'I' 'I' -0.4742 1.8119 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting triclinic _symmetry_space_group_name_H-M P-1 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 4.190(1) _cell_length_b 11.746(2) _cell_length_c 14.294(3) _cell_angle_alpha 95.18(1) _cell_angle_beta 91.92(1) _cell_angle_gamma 96.69(1) _cell_volume 695.2(3) _cell_formula_units_Z 2 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used 35 _cell_measurement_theta_min 7 _cell_measurement_theta_max 13 _exptl_crystal_description needle _exptl_crystal_colour red _exptl_crystal_size_max 0.4 _exptl_crystal_size_mid 0.2 _exptl_crystal_size_min 0.2 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 3.382 _exptl_crystal_density_method ? _exptl_crystal_F_000 624 _exptl_absorpt_coefficient_mu 9.528 _exptl_absorpt_correction_type 'integration' _exptl_absorpt_correction_T_min 0.115 _exptl_absorpt_correction_T_max 0.252 _exptl_absorpt_process_details 'SHELXTL (XPREP, 1997) program' _exptl_special_details ; ? ; _diffrn_ambient_temperature 293(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device 'Syntex P\=1' _diffrn_measurement_method '2\q/\w scan' _diffrn_standards_number 2 _diffrn_standards_interval_count 98 _diffrn_standards_interval_time . _diffrn_standards_decay_% 2 _diffrn_reflns_number 3149 _diffrn_reflns_av_R_equivalents 0.0219 _diffrn_reflns_av_sigmaI/netI 0.0191 _diffrn_reflns_limit_h_min 0 _diffrn_reflns_limit_h_max 4 _diffrn_reflns_limit_k_min -16 _diffrn_reflns_limit_k_max 16 _diffrn_reflns_limit_l_min -20 _diffrn_reflns_limit_l_max 20 _diffrn_reflns_theta_min 1.43 _diffrn_reflns_theta_max 29.99 _reflns_number_total 2640 _reflns_number_observed 2377 _reflns_observed_criterion I>2\s(I) _computing_data_collection 'P3, (Siemens, 1988)' _computing_cell_refinement 'P3, (Siemens, 1988)' _computing_data_reduction 'XDISK (Siemens, 1988)' _computing_structure_solution 'SHELXS-86 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-93 (Sheldrick, 1993)' _computing_molecular_graphics SHELXTL _computing_publication_material SHELXTL _refine_special_details ; Refinement on F^2^ for ALL reflections except for 10 with very negative F^2^ or flagged by the user for potential systematic errors. Weighted R-factors wR and all goodnesses of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The observed criterion of F^2^ > 2sigma(F^2^) is used only for calculating _R_factor_obs etc. and is not relevant to the choice of reflections for refinement. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme 'calc w=1/[\s^2^(Fo^2^)+(0.09P)^2^+6.0P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens . _refine_ls_hydrogen_treatment . _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 2630 _refine_ls_number_parameters 127 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0606 _refine_ls_R_factor_obs 0.0540 _refine_ls_wR_factor_all 0.1533 _refine_ls_wR_factor_obs 0.1409 _refine_ls_goodness_of_fit_all 1.140 _refine_ls_goodness_of_fit_obs 1.165 _refine_ls_restrained_S_all 1.202 _refine_ls_restrained_S_obs 1.165 _refine_ls_shift/esd_max 0.027 _refine_ls_shift/esd_mean 0.006 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_thermal_displace_type _atom_site_occupancy _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_group I2 I 0.6815(2) 0.68279(6) 0.18574(4) 0.0391(2) Uani 1 d . . I3 I 0.3511(2) 0.88969(6) 0.36920(5) 0.0438(2) Uani 1 d . . S1 S 0.6524(8) 0.5182(2) 0.3560(2) 0.0376(6) Uani 1 d . . S2 S 0.3882(7) 0.6778(2) 0.4966(2) 0.0371(6) Uani 1 d . . C1 C 0.5118(26) 0.5402(9) 0.4700(6) 0.032(2) Uani 1 d . . C2 C 0.5818(25) 0.6516(7) 0.3224(6) 0.030(2) Uani 1 d . . C3 C 0.4583(25) 0.7243(8) 0.3868(7) 0.032(2) Uani 1 d . . I5 I 0.8211(2) 0.60892(5) 0.88988(5) 0.0427(2) Uani 1 d . . I6 I 0.8767(2) 0.80522(6) 0.69415(4) 0.0381(2) Uani 1 d . . S3 S 1.2442(7) 0.8267(2) 1.0071(2) 0.0357(6) Uani 1 d . . S4 S 1.2910(7) 0.9816(2) 0.8552(2) 0.0361(6) Uani 1 d . . C4 C 1.3980(25) 0.9604(7) 0.9720(6) 0.028(2) Uani 1 d . . C5 C 1.0604(25) 0.7759(8) 0.8985(7) 0.030(2) Uani 1 d . . C6 C 1.0742(24) 0.8458(8) 0.8305(6) 0.030(2) Uani 1 d . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 I2 0.0552(5) 0.0367(4) 0.0267(4) 0.0063(3) 0.0067(3) 0.0060(3) I3 0.0555(5) 0.0273(3) 0.0488(4) -0.0003(3) 0.0014(3) 0.0094(3) S1 0.064(2) 0.0265(10) 0.0237(11) 0.0015(8) 0.0026(11) 0.0106(11) S2 0.056(2) 0.0326(11) 0.0220(11) -0.0025(9) 0.0004(10) 0.0080(11) C1 0.041(6) 0.035(5) 0.019(4) -0.001(3) -0.006(4) 0.004(4) C2 0.044(6) 0.021(4) 0.025(4) 0.002(3) -0.002(4) 0.000(4) C3 0.034(5) 0.032(4) 0.027(4) -0.003(4) -0.004(4) -0.002(4) I5 0.0475(5) 0.0251(3) 0.0514(5) -0.0044(3) -0.0035(3) -0.0047(3) I6 0.0459(4) 0.0400(4) 0.0250(3) -0.0107(2) -0.0096(3) 0.0049(3) S3 0.054(2) 0.0266(10) 0.0229(11) -0.0005(8) -0.0079(11) -0.0036(11) S4 0.059(2) 0.0242(10) 0.0216(10) -0.0025(8) -0.0082(11) -0.0044(11) C4 0.041(5) 0.021(4) 0.022(4) -0.007(3) -0.001(4) 0.005(4) C5 0.036(5) 0.022(4) 0.030(5) -0.004(3) -0.002(4) 0.003(4) C6 0.036(5) 0.027(4) 0.024(4) -0.009(3) -0.002(4) 0.004(4) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag I3 C3 2.079(10) . ? I2 C2 2.067(9) . ? S1 C2 1.734(9) . ? S1 C1 1.759(10) . ? S2 C3 1.731(10) . ? S2 C1 1.766(10) . ? C2 C3 1.356(13) . ? C1 C1 1.33(2) 2_666 ? I5 C5 2.088(9) . ? I6 C6 2.084(9) . ? S3 C5 1.733(10) . ? S3 C4 1.750(10) . ? S4 C6 1.741(10) . ? S4 C4 1.761(9) . ? C5 C6 1.326(14) . ? C4 C4 1.37(2) 2_877 ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C2 S1 C1 95.7(5) . . ? C1 S2 C3 95.5(5) . . ? C3 C2 S1 117.3(7) . . ? C3 C2 I2 126.1(7) . . ? S1 C2 I2 116.6(5) . . ? C2 C3 S2 117.6(8) . . ? C2 C3 I3 126.8(7) . . ? S2 C3 I3 115.6(5) . . ? C1 C1 S2 122.6(10) 2_666 . ? C1 C1 S1 123.5(11) 2_666 . ? S2 C1 S1 113.9(5) . . ? C5 S3 C4 94.8(4) . . ? C6 S4 C4 94.7(4) . . ? C6 C5 S3 118.4(7) . . ? C6 C5 I5 126.2(7) . . ? S3 C5 I5 115.4(5) . . ? C5 C6 S4 117.4(7) . . ? C5 C6 I6 125.8(7) . . ? S4 C6 I6 116.7(5) . . ? C4 C4 S3 123.2(10) 2_877 . ? C4 C4 S4 122.2(10) 2_877 . ? S3 C4 S4 114.5(5) . . ? _refine_diff_density_max 2.291 _refine_diff_density_min -2.861 _refine_diff_density_rms 0.353 #===============================================END data_5 _database_code_CSD 161755 _audit_creation_method SHELXL _chemical_name_systematic ;4-iodo-4',5,5'-trimethyltetrathiafulvalene ; _chemical_name_common ? _chemical_formula_moiety ? _chemical_formula_sum 'C9 H9 I S4' _chemical_formula_weight 372.30 _chemical_melting_point ? _chemical_compound_source ? _ccdc_compound_id '5' _ccdc_biological_activity '?' _ccdc_polymorph '?' _ccdc_disorder ; The iodine atom is disordered over all four positions I(2), I(3), I(5) and I(6), with occupancies (refined to) 74.1(5), 4.4(5), 18.1(5) and 3.3(7)%. respectively. The methyl group at C(2) (supposed occupancy of 26%) was not revealed and attempts to introduce it into the calculated position gave worse results. ; _ccdc_comments '?' loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source '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' 'S' 'S' 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 'I' 'I' -0.4742 1.8119 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Monoclinic _symmetry_space_group_name_H-M P2(1) loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y+1/2, -z' _cell_length_a 6.225(1) _cell_length_b 15.209(2) _cell_length_c 6.766(1) _cell_angle_alpha 90.00 _cell_angle_beta 96.65(1) _cell_angle_gamma 90.00 _cell_volume 636.3(2) _cell_formula_units_Z 2 _cell_measurement_temperature 295(2) _cell_measurement_reflns_used 223 _cell_measurement_theta_min 10.3 _cell_measurement_theta_max 17.6 _exptl_crystal_description prism _exptl_crystal_colour orange _exptl_crystal_size_max 0.30 _exptl_crystal_size_mid 0.08 _exptl_crystal_size_min 0.02 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.943 _exptl_crystal_density_method ? _exptl_crystal_F_000 360 _exptl_absorpt_coefficient_mu 3.133 _exptl_absorpt_correction_type 'integration' _exptl_absorpt_correction_T_min 0.4068 _exptl_absorpt_correction_T_max 0.9258 _exptl_absorpt_process_details 'SHELXTL (XPREP,1997), R(int)=0.086 before correction' _exptl_special_details ; The data collection nominally covered a hemisphere of reciprocal space, by a combination of 4 sets of \w scans; each set at different \f and/or 2\q angles and each scan (20 sec exposure) covering 0.3\% in \w. Crystal to detector distance 4.51 cm. Crystal decay was monitored by repeating 50 initial frames at the end of data collection and comparing 45 duplicate reflections. ; _diffrn_ambient_temperature 295(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device 'SMART 1K CCD area detector' _diffrn_measurement_method '\w scans' _diffrn_standards_number . _diffrn_standards_interval_count . _diffrn_standards_interval_time . _diffrn_standards_decay_% 0.48 _diffrn_reflns_number 5227 _diffrn_reflns_av_R_equivalents 0.0719 _diffrn_reflns_av_sigmaI/netI 0.0745 _diffrn_reflns_limit_h_min -8 _diffrn_reflns_limit_h_max 8 _diffrn_reflns_limit_k_min -21 _diffrn_reflns_limit_k_max 16 _diffrn_reflns_limit_l_min -9 _diffrn_reflns_limit_l_max 9 _diffrn_reflns_theta_min 2.68 _diffrn_reflns_theta_max 30.01 _reflns_number_total 3112 _reflns_number_observed 2217 _reflns_observed_criterion I>2\s(I) _computing_data_collection 'Siemens SMART' _computing_cell_refinement 'Siemens SMART' _computing_data_reduction 'Siemens SAINT' _computing_structure_solution 'SHELXS-86 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-93 (Sheldrick, 1993)' _computing_molecular_graphics 'SHELXTL' _computing_publication_material 'SHELXTL' _refine_special_details ; Racemic twin with contributions refined to 44(7) and 56(7)%. Refinement on F^2^ for ALL reflections except for 44 with very negative F^2^. Weighted R-factors wR and all goodnesses of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The observed criterion of F^2^ > 2sigma(F^2^) is used only for calculating _R_factor_obs etc. and is not relevant to the choice of reflections for refinement. Methyl groups refined as rigid rotating bodies. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme 'calc w=1/[\s^2^(Fo^2^)+(0.0466P)^2^+3.4253P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment constr _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881' _refine_ls_abs_structure_Flack 0.56(7) _refine_ls_number_reflns 3068 _refine_ls_number_parameters 142 _refine_ls_number_restraints 9 _refine_ls_R_factor_all 0.1238 _refine_ls_R_factor_obs 0.0782 _refine_ls_wR_factor_all 0.2208 _refine_ls_wR_factor_obs 0.1643 _refine_ls_goodness_of_fit_all 1.272 _refine_ls_goodness_of_fit_obs 1.243 _refine_ls_restrained_S_all 1.414 _refine_ls_restrained_S_obs 1.255 _refine_ls_shift/esd_max 0.007 _refine_ls_shift/esd_mean 0.001 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_thermal_displace_type _atom_site_occupancy _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_group S1 S 0.4310(7) 0.3787(3) 0.3937(6) 0.0563(10) Uani 1 d . . S2 S 0.4391(6) 0.4643(2) 0.0021(6) 0.0539(9) Uani 1 d . . S3 S 0.0387(6) 0.5068(3) 0.4898(7) 0.0510(10) Uani 1 d . . S4 S 0.0484(7) 0.5949(3) 0.1042(6) 0.0569(10) Uani 1 d . . C1 C 0.3205(20) 0.4587(9) 0.2260(19) 0.046(3) Uani 1 d . . C2 C 0.6345(19) 0.3469(8) 0.2464(20) 0.045(3) Uani 1 d D . C3 C 0.6374(18) 0.3843(9) 0.0709(18) 0.043(3) Uani 1 d D . C4 C 0.1580(20) 0.5125(9) 0.2691(21) 0.049(3) Uani 1 d . . C5 C -0.1610(20) 0.5856(9) 0.4301(20) 0.047(3) Uani 1 d D . C6 C -0.1525(20) 0.6260(9) 0.2503(22) 0.050(3) Uani 1 d D . C15 C -0.3288(22) 0.6005(10) 0.5813(21) 0.041(3) Uani 0.967(7) d PD 1 H151 H -0.2566(25) 0.6192(57) 0.7079(42) 0.062 Uiso 1 d R 1 H152 H -0.4096(104) 0.5477(20) 0.5993(105) 0.062 Uiso 1 d R 1 H153 H -0.4259(88) 0.6462(43) 0.5288(65) 0.062 Uiso 1 d R 1 I2 I 0.8385(2) 0.25302(9) 0.3681(2) 0.0560(4) Uani 0.741(5) d PD 1 I3 I 0.8501(44) 0.3620(19) -0.1050(40) 0.052(9) Uiso 0.044(5) d PD 2 C13 C 0.7961(34) 0.3652(16) -0.0759(33) 0.071(7) Uiso 0.956(5) d PD 1 H131 H 0.8171(163) 0.4163(30) -0.1548(135) 0.107 Uiso 0.956(5) d PR 1 H132 H 0.7396(104) 0.3182(60) -0.1615(129) 0.107 Uiso 0.956(5) d PR 1 H133 H 0.9321(72) 0.3476(83) -0.0053(34) 0.107 Uiso 0.956(5) d PR 1 I6 I -0.3342(12) 0.7174(6) 0.1307(14) 0.055(2) Uani 0.181(5) d PD 2 C16 C -0.3164(44) 0.6959(18) 0.1512(45) 0.056(10) Uiso 0.819(5) d PD 1 H161 H -0.3818(149) 0.6727(38) 0.0263(93) 0.085 Uiso 0.819(5) d PR 1 H162 H -0.2364(52) 0.7482(33) 0.1277(167) 0.085 Uiso 0.819(5) d PR 1 H163 H -0.4276(117) 0.7103(59) 0.2334(88) 0.085 Uiso 0.819(5) d PR 1 I5 I -0.3630(126) 0.6375(62) 0.6168(121) 0.158(46) Uiso 0.033(7) d PD 2 loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 S1 0.050(2) 0.066(3) 0.054(2) 0.016(2) 0.013(2) 0.013(2) S2 0.051(2) 0.063(2) 0.048(2) 0.009(2) 0.007(2) 0.010(2) S3 0.051(2) 0.056(2) 0.047(2) 0.0059(15) 0.011(2) 0.007(2) S4 0.057(2) 0.062(2) 0.053(2) 0.012(2) 0.009(2) 0.011(2) C1 0.038(6) 0.057(8) 0.043(7) 0.001(6) 0.003(5) 0.004(6) C2 0.039(6) 0.045(8) 0.052(8) -0.001(6) 0.006(6) -0.001(5) C3 0.033(6) 0.052(8) 0.043(7) -0.002(6) 0.005(5) -0.002(5) C4 0.035(6) 0.050(8) 0.059(9) 0.004(7) -0.005(6) -0.003(6) C5 0.041(7) 0.041(7) 0.058(8) -0.014(6) 0.000(6) -0.006(5) C6 0.046(7) 0.044(8) 0.059(9) -0.004(7) -0.002(6) -0.001(6) C15 0.039(7) 0.040(8) 0.044(8) -0.013(6) 0.004(5) -0.008(6) I2 0.0480(6) 0.0498(6) 0.0702(7) 0.0061(8) 0.0066(5) 0.0171(7) I6 0.050(3) 0.047(4) 0.068(4) 0.001(3) 0.004(3) 0.024(3) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag S1 C1 1.749(14) . ? S1 C2 1.768(13) . ? S2 C3 1.757(13) . ? S2 C1 1.763(13) . ? S3 C5 1.740(14) . ? S3 C4 1.74(2) . ? S4 C6 1.746(15) . ? S4 C4 1.762(14) . ? C1 C4 1.36(2) . ? C2 C3 1.32(2) . ? C2 I2 2.022(12) . ? C3 C13 1.51(2) . ? C3 I3 1.91(2) . ? C5 C6 1.37(2) . ? C5 C15 1.56(2) . ? C5 I5 2.04(3) . ? C6 C16 1.57(2) . ? C6 I6 1.912(14) . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C1 S1 C2 94.5(6) . . ? C3 S2 C1 95.2(6) . . ? C5 S3 C4 97.5(6) . . ? C6 S4 C4 94.8(7) . . ? C4 C1 S1 121.7(9) . . ? C4 C1 S2 123.5(9) . . ? S1 C1 S2 114.8(7) . . ? C3 C2 S1 118.3(9) . . ? C3 C2 I2 126.7(10) . . ? S1 C2 I2 114.9(7) . . ? C2 C3 C13 126.0(14) . . ? C2 C3 S2 117.1(9) . . ? C13 C3 S2 116.9(12) . . ? C2 C3 I3 124.5(13) . . ? S2 C3 I3 118.3(11) . . ? C1 C4 S3 123.7(9) . . ? C1 C4 S4 122.4(10) . . ? S3 C4 S4 113.9(8) . . ? C6 C5 C15 127.9(13) . . ? C6 C5 S3 114.5(10) . . ? C15 C5 S3 117.5(10) . . ? C6 C5 I5 117.8(31) . . ? S3 C5 I5 126.7(30) . . ? C5 C6 C16 126.4(16) . . ? C5 C6 S4 119.0(10) . . ? C16 C6 S4 114.5(14) . . ? C5 C6 I6 128.4(11) . . ? S4 C6 I6 112.6(8) . . ? _refine_diff_density_max 0.676 _refine_diff_density_min -0.689 _refine_diff_density_rms 0.141 #===============================================END data_6 _database_code_CSD 161756 _audit_creation_method SHELXL _chemical_name_systematic ;4-bromo-4',5,5'-trimethyltetrathiafulvalene ; _chemical_name_common ? _chemical_formula_moiety ? _chemical_formula_sum 'C9 H9 Br S4' _chemical_formula_weight 325.31 _chemical_melting_point '174--175\% C' _chemical_compound_source ? _ccdc_compound_id '6' _ccdc_biological_activity '?' _ccdc_polymorph '?' _ccdc_disorder ; Bromine and methyl substituents are statistically distributed between all four positions (25% Br and 75% Me in each). ; _ccdc_comments 'isostructural with 8' loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source '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' 'S' 'S' 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 'Br' 'Br' -0.2901 2.4595 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Triclinic _symmetry_space_group_name_H-M P-1 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 6.033(2) _cell_length_b 6.830(1) _cell_length_c 7.862(4) _cell_angle_alpha 107.70(2) _cell_angle_beta 103.17(1) _cell_angle_gamma 95.81(1) _cell_volume 295.4(2) _cell_formula_units_Z 1 _cell_measurement_temperature 150(2) _cell_measurement_reflns_used 413 _cell_measurement_theta_min 10.4 _cell_measurement_theta_max 27.6 _exptl_crystal_description plate _exptl_crystal_colour orange _exptl_crystal_size_max 0.25 _exptl_crystal_size_mid 0.15 _exptl_crystal_size_min 0.04 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.829 _exptl_crystal_density_method ? _exptl_crystal_F_000 162 _exptl_absorpt_coefficient_mu 4.143 _exptl_absorpt_correction_type integration _exptl_absorpt_correction_T_min 0.4776 _exptl_absorpt_correction_T_max 0.8544 _exptl_absorpt_process_details 'SHELXTL (XPREP,1997)' loop_ _exptl_crystal_face_index_h _exptl_crystal_face_index_k _exptl_crystal_face_index_l _exptl_crystal_face_perp_dist 0.00 0.00 1.00 0.0200 0.00 0.00 -1.00 0.0200 0.00 -1.00 0.00 0.0500 -2.00 2.00 1.00 0.0800 0.00 1.00 0.00 0.0800 1.00 0.00 0.00 0.1200 _exptl_special_details ; The data collection nominally covered over a hemisphere of reciprocal space, by a combination of 4 sets of \w scans; each set at different \f and/or 2\q angles and each scan (20 sec exposure) covering 0.3\% in \w. Crystal to detector distance 4.51 cm. Crystal decay was monitored by repeating 50 initial frames at the end of data collection and comparing 36 duplicate reflections. ; _diffrn_ambient_temperature 150(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device 'SMART 1K CCD area detector' _diffrn_measurement_method '\w scans' _diffrn_standards_number 0 _diffrn_standards_interval_count . _diffrn_standards_interval_time . _diffrn_standards_decay_% 0.6 _diffrn_reflns_number 2415 _diffrn_reflns_av_R_equivalents 0.0453 _diffrn_reflns_av_sigmaI/netI 0.0515 _diffrn_reflns_limit_h_min -4 _diffrn_reflns_limit_h_max 8 _diffrn_reflns_limit_k_min -9 _diffrn_reflns_limit_k_max 9 _diffrn_reflns_limit_l_min -10 _diffrn_reflns_limit_l_max 9 _diffrn_reflns_theta_min 2.83 _diffrn_reflns_theta_max 28.98 _reflns_number_total 1533 _reflns_number_observed 1223 _reflns_observed_criterion >2sigma(I) _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'Bruker SMART' _computing_data_reduction 'Bruker SAINT' _computing_structure_solution 'SHELXS-86 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-93 (Sheldrick, 1993)' _computing_molecular_graphics SHELXTL _computing_publication_material SHELXTL _refine_special_details ; Refinement on F^2^ for ALL reflections except for 52 with very negative F^2^ or flagged by the user for potential systematic errors. Weighted R-factors wR and all goodnesses of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The observed criterion of F^2^ > 2sigma(F^2^) is used only for calculating _R_factor_obs etc. and is not relevant to the choice of reflections for refinement. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme 'calc w=1/[\s^2^(Fo^2^)+(0.0351P)^2^+0.7877P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment constr _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 1481 _refine_ls_number_parameters 74 _refine_ls_number_restraints 2 _refine_ls_R_factor_all 0.0783 _refine_ls_R_factor_obs 0.0556 _refine_ls_wR_factor_all 0.1555 _refine_ls_wR_factor_obs 0.1197 _refine_ls_goodness_of_fit_all 1.173 _refine_ls_goodness_of_fit_obs 1.173 _refine_ls_restrained_S_all 1.358 _refine_ls_restrained_S_obs 1.175 _refine_ls_shift/esd_max -0.022 _refine_ls_shift/esd_mean 0.002 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_thermal_displace_type _atom_site_occupancy _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_group Br2 Br 0.2108(7) 0.2062(7) 0.0913(6) 0.0304(10) Uani 0.25 d P 2 Br3 Br 0.3197(6) 0.7275(6) 0.1840(6) 0.0295(8) Uani 0.25 d P 1 S1 S 0.69554(15) 0.25752(15) 0.32587(14) 0.0242(2) Uani 1 d . . S2 S 0.7955(2) 0.7152(2) 0.40385(14) 0.0256(3) Uani 1 d . . C1 C 0.8942(6) 0.4941(6) 0.4431(5) 0.0206(7) Uani 1 d . . C2 C 0.4706(6) 0.3719(6) 0.2315(5) 0.0230(7) Uani 1 d D . C3 C 0.5163(6) 0.5780(6) 0.2675(5) 0.0242(8) Uani 1 d D . C12 C 0.2403(24) 0.2204(27) 0.1074(24) 0.037(5) Uiso 0.75 d PD 1 H121 H 0.1844(48) 0.1397(57) 0.1780(33) 0.055 Uiso 0.75 d PR 1 H122 H 0.2680(30) 0.1248(55) -0.0039(40) 0.055 Uiso 0.75 d PR 1 H123 H 0.1239(35) 0.3009(27) 0.0709(57) 0.055 Uiso 0.75 d PR 1 C13 C 0.3493(24) 0.7137(24) 0.1973(22) 0.035(4) Uiso 0.75 d PD 2 H131 H 0.3374(65) 0.8306(47) 0.3035(22) 0.053 Uiso 0.75 d PR 2 H132 H 0.1939(31) 0.6279(30) 0.1317(58) 0.053 Uiso 0.75 d PR 2 H133 H 0.4074(47) 0.7713(63) 0.1115(54) 0.053 Uiso 0.75 d PR 2 loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 Br2 0.0161(11) 0.0331(14) 0.0323(15) 0.0075(9) -0.0044(9) -0.0021(9) Br3 0.0194(11) 0.0371(14) 0.0353(14) 0.0186(10) 0.0024(8) 0.0114(10) S1 0.0168(4) 0.0238(5) 0.0278(5) 0.0070(4) 0.0003(3) 0.0039(3) S2 0.0168(4) 0.0262(5) 0.0326(5) 0.0117(4) 0.0014(4) 0.0047(3) C1 0.015(2) 0.024(2) 0.024(2) 0.0101(14) 0.0044(13) 0.0034(13) C2 0.020(2) 0.032(2) 0.018(2) 0.0084(15) 0.0046(13) 0.0072(14) C3 0.015(2) 0.032(2) 0.024(2) 0.010(2) 0.0020(14) 0.0045(14) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag Br2 C2 1.746(6) . ? Br3 C3 1.783(6) . ? S1 C1 1.760(4) . ? S1 C2 1.763(4) . ? S2 C1 1.764(4) . ? S2 C3 1.764(4) . ? C1 C1 1.360(7) 2_766 ? C2 C3 1.335(6) . ? C2 C12 1.559(13) . ? C3 C13 1.557(12) . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C1 S1 C2 95.3(2) . . ? C1 S2 C3 94.8(2) . . ? C1 C1 S1 122.7(4) 2_766 . ? C1 C1 S2 122.7(4) 2_766 . ? S1 C1 S2 114.6(2) . . ? C3 C2 C12 126.3(7) . . ? C3 C2 Br2 125.2(3) . . ? C3 C2 S1 117.1(3) . . ? C12 C2 S1 116.6(7) . . ? Br2 C2 S1 117.7(3) . . ? C2 C3 C13 126.8(7) . . ? C2 C3 S2 118.0(3) . . ? C13 C3 S2 115.2(6) . . ? C2 C3 Br3 125.3(3) . . ? S2 C3 Br3 116.7(3) . . ? _refine_diff_density_max 0.479 _refine_diff_density_min -0.680 _refine_diff_density_rms 0.130 #===============================================END data_8 _database_code_CSD 161757 _audit_creation_method SHELXL-97 _chemical_name_systematic ; 4,4',5,5'-tetramethyltetrathiafulvalene ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C10 H12 S4' _chemical_formula_weight 260.44 _ccdc_compound_id '8' _ccdc_biological_activity '?' _ccdc_polymorph '?' _ccdc_disorder 'none' _ccdc_comments '?' loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source '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' 'S' 'S' 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Triclinic _symmetry_space_group_name_H-M P-1 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 6.0472(3) _cell_length_b 6.7723(4) _cell_length_c 7.7964(4) _cell_angle_alpha 107.635(2) _cell_angle_beta 103.913(2) _cell_angle_gamma 96.561(2) _cell_volume 289.25(3) _cell_formula_units_Z 1 _cell_measurement_temperature 120(2) _cell_measurement_reflns_used 996 _cell_measurement_theta_min 10.6 _cell_measurement_theta_max 26.2 _exptl_crystal_description plate _exptl_crystal_colour orange _exptl_crystal_size_max 0.50 _exptl_crystal_size_mid 0.14 _exptl_crystal_size_min 0.07 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.495 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 136 _exptl_absorpt_coefficient_mu 0.778 _exptl_absorpt_correction_type integration _exptl_absorpt_correction_T_min 0.7722 _exptl_absorpt_correction_T_max 0.9504 _exptl_absorpt_process_details 'XPREP (SHELXTL, 1997) program' loop_ _exptl_crystal_face_index_h _exptl_crystal_face_index_k _exptl_crystal_face_index_l _exptl_crystal_face_perp_dist 0.00 1.00 0.00 0.0350 0.00 -1.00 0.00 0.0350 0.00 0.00 1.00 0.0700 0.00 0.00 -1.00 0.0700 -1.00 0.00 1.00 0.1800 -1.00 0.00 0.00 0.2000 1.00 0.00 -1.00 0.2000 _exptl_special_details ; The data collection nominally covered full sphere of reciprocal space, by a combination of 5 sets of \w scans; each set at different \f and/or 2\q angles and each scan (15 sec exposure) covering 0.3\% in \w. Crystal to detector distance 4.51 cm. ; _diffrn_ambient_temperature 120(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'SMART 1K CCD area detector' _diffrn_measurement_method '\w scans' _diffrn_detector_area_resol_mean 8 _diffrn_standards_number . _diffrn_standards_interval_count . _diffrn_standards_interval_time . _diffrn_standards_decay_% 0 _diffrn_reflns_number 3566 _diffrn_reflns_av_R_equivalents 0.0375 _diffrn_reflns_av_sigmaI/netI 0.0283 _diffrn_reflns_limit_h_min -7 _diffrn_reflns_limit_h_max 8 _diffrn_reflns_limit_k_min -9 _diffrn_reflns_limit_k_max 8 _diffrn_reflns_limit_l_min -10 _diffrn_reflns_limit_l_max 10 _diffrn_reflns_theta_min 2.87 _diffrn_reflns_theta_max 29.13 _reflns_number_total 1512 _reflns_number_gt 1366 _reflns_threshold_expression I>2\s(I) _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'Bruker SMART' _computing_data_reduction 'Bruker SHELXTL' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Bruker SHELXTL' _computing_publication_material 'Bruker SHELXTL' _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0363P)^2^+0.0705P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens difmap _refine_ls_hydrogen_treatment refall _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 1512 _refine_ls_number_parameters 88 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0287 _refine_ls_R_factor_gt 0.0247 _refine_ls_wR_factor_ref 0.0656 _refine_ls_wR_factor_gt 0.0633 _refine_ls_goodness_of_fit_ref 1.066 _refine_ls_restrained_S_all 1.066 _refine_ls_shift/su_max 0.001 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group S1 S 0.31105(5) 0.74831(5) 0.17119(4) 0.01755(10) Uani 1 1 d . . . S2 S 0.20411(5) 0.29077(5) 0.10934(4) 0.01896(10) Uani 1 1 d . . . C1 C 0.1067(2) 0.5080(2) 0.05823(17) 0.0165(2) Uani 1 1 d . . . C2 C 0.5393(2) 0.6373(2) 0.26880(17) 0.0172(2) Uani 1 1 d . . . C3 C 0.4904(2) 0.4293(2) 0.23998(17) 0.0173(2) Uani 1 1 d . . . C4 C 0.7663(2) 0.7897(2) 0.3802(2) 0.0220(3) Uani 1 1 d . . . H41 H 0.824(3) 0.862(3) 0.304(3) 0.046(6) Uiso 1 1 d . . . H42 H 0.753(4) 0.894(4) 0.487(4) 0.062(7) Uiso 1 1 d . . . H43 H 0.876(4) 0.722(4) 0.427(3) 0.043(6) Uiso 1 1 d . . . C5 C 0.6541(2) 0.2999(2) 0.3091(2) 0.0226(3) Uani 1 1 d . . . H51 H 0.647(4) 0.171(4) 0.205(3) 0.057(7) Uiso 1 1 d . . . H52 H 0.618(4) 0.263(4) 0.393(4) 0.068(8) Uiso 1 1 d . . . H53 H 0.806(4) 0.375(4) 0.367(3) 0.054(6) Uiso 1 1 d . . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 S1 0.01223(15) 0.01707(16) 0.02032(16) 0.00567(12) 0.00040(11) 0.00254(11) S2 0.01319(15) 0.01803(17) 0.02360(17) 0.00816(12) 0.00070(11) 0.00236(11) C1 0.0126(5) 0.0171(6) 0.0185(5) 0.0057(4) 0.0026(4) 0.0032(4) C2 0.0110(5) 0.0231(6) 0.0151(5) 0.0059(4) 0.0004(4) 0.0038(4) C3 0.0120(5) 0.0222(6) 0.0169(5) 0.0072(4) 0.0018(4) 0.0043(4) C4 0.0136(5) 0.0235(7) 0.0233(6) 0.0063(5) -0.0014(5) 0.0012(5) C5 0.0170(6) 0.0254(7) 0.0260(6) 0.0126(6) 0.0015(5) 0.0061(5) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag S1 C1 1.7606(13) . ? S1 C2 1.7688(12) . ? S2 C1 1.7640(13) . ? S2 C3 1.7655(13) . ? C1 C1 1.358(2) 2_565 ? C2 C3 1.3423(19) . ? C2 C4 1.5047(17) . ? C3 C5 1.5057(17) . ? C4 H41 0.97(2) . ? C4 H42 0.94(3) . ? C4 H43 0.91(2) . ? C5 H51 0.99(2) . ? C5 H52 0.83(3) . ? C5 H53 0.93(2) . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C1 S1 C2 95.69(6) . . ? C1 S2 C3 95.60(6) . . ? C1 C1 S1 122.83(13) 2_565 . ? C1 C1 S2 123.16(13) 2_565 . ? S1 C1 S2 114.01(6) . . ? C3 C2 C4 127.23(11) . . ? C3 C2 S1 117.03(9) . . ? C4 C2 S1 115.72(10) . . ? C2 C3 C5 126.85(12) . . ? C2 C3 S2 117.32(9) . . ? C5 C3 S2 115.83(10) . . ? C2 C4 H41 111.2(12) . . ? C2 C4 H42 112.2(15) . . ? H41 C4 H42 107.4(19) . . ? C2 C4 H43 111.1(14) . . ? H41 C4 H43 110.1(18) . . ? H42 C4 H43 105(2) . . ? C3 C5 H51 110.0(14) . . ? C3 C5 H52 110.9(18) . . ? H51 C5 H52 108(2) . . ? C3 C5 H53 113.3(15) . . ? H51 C5 H53 110.8(19) . . ? H52 C5 H53 104(2) . . ? _diffrn_measured_fraction_theta_max 0.970 _diffrn_reflns_theta_full 29.13 _diffrn_measured_fraction_theta_full 0.970 _refine_diff_density_max 0.298 _refine_diff_density_min -0.331 _refine_diff_density_rms 0.066 #===============================================END data_15 _database_code_CSD 161758 _audit_creation_method SHELXL _chemical_name_systematic ; 4,5-dibromo-4',5'-bis(2'-cyanoethylsulfanyl)- tetrathiafulvalene ; _chemical_name_common ? _chemical_formula_moiety ? _chemical_formula_sum 'C12 H8 Br2 N2 S6' _chemical_formula_weight 532.38 _chemical_melting_point '132--134\% C' _chemical_compound_source ? _ccdc_compound_id '15' _ccdc_biological_activity '?' _ccdc_polymorph '?' _ccdc_disorder 'none' _ccdc_comments '?' 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' 'Br' 'Br' -.2901 2.4595 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting 'Orthorhombic' _symmetry_space_group_name_H-M 'Pbca ' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, -y, z+1/2' '-x, y+1/2, -z+1/2' 'x+1/2, -y+1/2, -z' '-x, -y, -z' 'x-1/2, y, -z-1/2' 'x, -y-1/2, z-1/2' '-x-1/2, y-1/2, z' _cell_length_a 14.609(1) _cell_length_b 11.607(1) _cell_length_c 21.020(1) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 3564.3(4) _cell_formula_units_Z 8 _cell_measurement_temperature 150(2) _cell_measurement_reflns_used 262 _cell_measurement_theta_min 12.1 _cell_measurement_theta_max 25.9 _exptl_crystal_description block _exptl_crystal_colour scarlet _exptl_crystal_size_max 0.40 _exptl_crystal_size_mid 0.30 _exptl_crystal_size_min 0.25 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.984 _exptl_crystal_density_method ? _exptl_crystal_F_000 2080 _exptl_absorpt_coefficient_mu 5.246 _exptl_absorpt_correction_type 'integration' _exptl_absorpt_correction_T_min 0.1762 _exptl_absorpt_correction_T_max 0.3664 loop_ _exptl_crystal_face_index_h _exptl_crystal_face_index_k _exptl_crystal_face_index_l _exptl_crystal_face_perp_dist 1.00 -1.00 1.00 0.2000 1.00 -1.00 -1.00 0.1800 -1.00 1.00 1.00 0.1400 0.00 0.00 -1.00 0.1200 0.00 0.00 1.00 0.1200 -1.00 -1.00 -1.00 0.1800 1.00 0.00 0.00 0.2000 5.00 1.00 -1.00 0.1800 _exptl_special_details ; The data collection nominally covered over a hemisphere of reciprocal space, by a combination of 5 sets of \w scans; each set at different \f and/or 2\q angles and each scan (20 sec exposure) covering 0.3\% in \w. Crystal to detector distance 4.51 cm. Crystal decay was monitored by repeating 50 initial frames at the end of data collection and comparing 502 duplicate reflections. ; _diffrn_ambient_temperature 150(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device 'SMART 1K CCD area detector' _diffrn_measurement_method '\w scan' _diffrn_standards_number . _diffrn_standards_interval_count . _diffrn_standards_interval_time . _diffrn_standards_decay_% 0.1 _diffrn_reflns_number 27012 _diffrn_reflns_av_R_equivalents 0.0566 _diffrn_reflns_av_sigmaI/netI 0.0300 _diffrn_reflns_limit_h_min -20 _diffrn_reflns_limit_h_max 20 _diffrn_reflns_limit_k_min -16 _diffrn_reflns_limit_k_max 16 _diffrn_reflns_limit_l_min -27 _diffrn_reflns_limit_l_max 28 _diffrn_reflns_theta_min 1.94 _diffrn_reflns_theta_max 30.48 _reflns_number_total 5108 _reflns_number_observed 4324 _reflns_observed_criterion >2sigma(I) _computing_data_collection 'Siemens SMART' _computing_cell_refinement 'Siemens SMART' _computing_data_reduction 'Siemens SAINT' _computing_structure_solution 'SHELXS-86 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-93 (Sheldrick, 1993)' _computing_molecular_graphics 'Siemens SHELXTL' _computing_publication_material 'Siemens SHELXTL' _refine_special_details ; Refinement on F^2^ for ALL reflections except for 22 with very negative F^2^ or flagged by the user for potential systematic errors. Weighted R-factors wR and all goodnesses of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The observed criterion of F^2^ > 2sigma(F^2^) is used only for calculating _R_factor_obs etc. and is not relevant to the choice of reflections for refinement. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme 'calc w=1/[\s^2^(Fo^2^)+(0.0113P)^2^+4.2021P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens difmap _refine_ls_hydrogen_treatment refall _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 5086 _refine_ls_number_parameters 231 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0411 _refine_ls_R_factor_obs 0.0291 _refine_ls_wR_factor_all 0.0655 _refine_ls_wR_factor_obs 0.0571 _refine_ls_goodness_of_fit_all 1.209 _refine_ls_goodness_of_fit_obs 1.185 _refine_ls_restrained_S_all 1.247 _refine_ls_restrained_S_obs 1.185 _refine_ls_shift/esd_max -0.001 _refine_ls_shift/esd_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_thermal_displace_type _atom_site_occupancy _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_group Br1 Br 0.790363(15) 0.73529(2) 0.494410(12) 0.02340(6) Uani 1 d . . Br2 Br 0.62590(2) 0.95095(2) 0.466195(13) 0.02586(6) Uani 1 d . . S1 S 0.64143(4) 0.56743(5) 0.44731(3) 0.02044(12) Uani 1 d . . S2 S 0.50211(4) 0.75056(5) 0.42318(3) 0.02216(12) Uani 1 d . . S3 S 0.49537(4) 0.37247(5) 0.40821(3) 0.02127(12) Uani 1 d . . S4 S 0.35613(4) 0.55129(5) 0.38020(3) 0.02157(12) Uani 1 d . . S5 S 0.37331(4) 0.17766(5) 0.36439(3) 0.02286(12) Uani 1 d . . S6 S 0.21759(4) 0.38054(5) 0.33199(3) 0.02038(12) Uani 1 d . . C1 C 0.52927(15) 0.6022(2) 0.42193(11) 0.0180(4) Uani 1 d . . C2 C 0.67142(15) 0.7109(2) 0.46315(11) 0.0179(4) Uani 1 d . . C3 C 0.60935(15) 0.7927(2) 0.45264(11) 0.0191(4) Uani 1 d . . C4 C 0.46906(15) 0.5203(2) 0.40437(11) 0.0187(4) Uani 1 d . . C5 C 0.39229(15) 0.3262(2) 0.37262(11) 0.0181(4) Uani 1 d . . C6 C 0.32873(15) 0.4078(2) 0.36021(11) 0.0180(4) Uani 1 d . . C7 C 0.4836(2) 0.1242(2) 0.33670(13) 0.0251(5) Uani 1 d . . H71 H 0.4796(21) 0.0433(28) 0.3455(15) 0.030(8) Uiso 1 d . . H72 H 0.5307(22) 0.1540(28) 0.3619(15) 0.036(9) Uiso 1 d . . C8 C 0.5036(2) 0.1455(2) 0.26630(14) 0.0318(6) Uani 1 d . . H81 H 0.5634(24) 0.1114(29) 0.2548(16) 0.041(9) Uiso 1 d . . H82 H 0.4628(27) 0.1160(35) 0.2425(19) 0.055(12) Uiso 1 d . . C9 C 0.5075(2) 0.2687(2) 0.24979(12) 0.0243(5) Uani 1 d . . C10 C 0.2197(2) 0.4604(2) 0.25725(12) 0.0209(4) Uani 1 d . . H101 H 0.2392(19) 0.5344(26) 0.2650(13) 0.022(7) Uiso 1 d . . H102 H 0.1573(22) 0.4614(26) 0.2452(14) 0.028(8) Uiso 1 d . . C11 C 0.2765(2) 0.4043(2) 0.20515(13) 0.0266(5) Uani 1 d . . H111 H 0.2720(22) 0.4514(29) 0.1695(16) 0.036(9) Uiso 1 d . . H112 H 0.3367(26) 0.3985(31) 0.2183(17) 0.048(10) Uiso 1 d . . C12 C 0.2440(2) 0.2878(2) 0.18965(12) 0.0271(5) Uani 1 d . . N1 N 0.5088(2) 0.3640(2) 0.23670(12) 0.0316(5) Uani 1 d . . N2 N 0.2169(2) 0.1980(2) 0.17822(12) 0.0410(6) Uani 1 d . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 Br1 0.01596(10) 0.02346(12) 0.03077(13) -0.00573(10) -0.00369(9) -0.00320(8) Br2 0.02521(11) 0.01627(11) 0.03609(14) -0.00155(10) 0.00229(10) -0.00209(9) S1 0.0152(2) 0.0165(3) 0.0296(3) -0.0038(2) -0.0038(2) -0.0003(2) S2 0.0174(2) 0.0192(3) 0.0299(3) -0.0004(2) -0.0047(2) 0.0007(2) S3 0.0177(2) 0.0188(3) 0.0273(3) -0.0054(2) -0.0048(2) 0.0014(2) S4 0.0158(2) 0.0196(3) 0.0294(3) -0.0061(2) -0.0049(2) 0.0010(2) S5 0.0223(3) 0.0181(3) 0.0282(3) -0.0036(2) 0.0045(2) -0.0046(2) S6 0.0148(2) 0.0238(3) 0.0225(3) -0.0009(2) -0.0011(2) -0.0050(2) C1 0.0151(9) 0.0194(11) 0.0195(11) -0.0023(8) -0.0004(8) 0.0000(8) C2 0.0146(9) 0.0191(10) 0.0201(10) -0.0027(9) 0.0004(8) -0.0035(8) C3 0.0177(10) 0.0162(10) 0.0235(11) -0.0007(9) 0.0009(8) -0.0038(8) C4 0.0159(9) 0.0197(11) 0.0206(11) -0.0026(9) -0.0015(8) -0.0002(8) C5 0.0175(10) 0.0181(11) 0.0189(10) -0.0035(8) 0.0004(8) -0.0035(8) C6 0.0157(9) 0.0198(11) 0.0184(10) -0.0037(8) 0.0013(8) -0.0034(8) C7 0.0266(12) 0.0177(12) 0.0309(13) -0.0004(10) 0.0029(10) 0.0015(9) C8 0.040(2) 0.0210(13) 0.0340(15) -0.0066(11) 0.0118(13) -0.0053(11) C9 0.0213(10) 0.0286(13) 0.0229(11) -0.0030(10) 0.0043(9) -0.0038(9) C10 0.0188(10) 0.0196(11) 0.0244(11) 0.0001(9) -0.0033(9) 0.0003(9) C11 0.0243(12) 0.0303(14) 0.0253(13) 0.0035(11) 0.0017(10) -0.0014(10) C12 0.0323(13) 0.0285(14) 0.0206(11) 0.0008(10) 0.0013(10) 0.0085(10) N1 0.0273(11) 0.0304(13) 0.0373(13) 0.0073(10) 0.0039(10) -0.0023(9) N2 0.059(2) 0.0306(13) 0.0328(13) -0.0041(11) 0.0039(12) 0.0039(12) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag Br1 C2 1.879(2) . y Br2 C3 1.875(2) . y S1 C2 1.754(2) . y S1 C1 1.770(2) . y S2 C3 1.754(2) . y S2 C1 1.767(2) . y S3 C4 1.760(2) . y S3 C5 1.765(2) . y S4 C4 1.763(2) . y S4 C6 1.764(2) . y S5 C5 1.755(2) . y S5 C7 1.822(3) . y S6 C6 1.757(2) . y S6 C10 1.825(3) . y C1 C4 1.347(3) . y C2 C3 1.331(3) . y C5 C6 1.351(3) . y C7 C8 1.528(4) . y C7 H71 0.96(3) . ? C7 H72 0.94(3) . ? C8 C9 1.472(4) . y C8 H81 0.99(4) . ? C8 H82 0.85(4) . ? C9 N1 1.140(3) . y C10 C11 1.521(4) . y C10 H101 0.92(3) . ? C10 H102 0.95(3) . ? C11 C12 1.470(4) . y C11 H111 0.93(3) . ? C11 H112 0.92(4) . ? C12 N2 1.141(4) . y loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C2 S1 C1 94.11(11) . . y C3 S2 C1 94.36(11) . . y C4 S3 C5 95.20(11) . . y C4 S4 C6 95.06(11) . . y C5 S5 C7 103.06(11) . . y C6 S6 C10 100.58(11) . . y C4 C1 S2 123.1(2) . . y C4 C1 S1 121.7(2) . . y S2 C1 S1 115.20(12) . . y C3 C2 S1 118.4(2) . . y C3 C2 Br1 125.5(2) . . y S1 C2 Br1 116.13(12) . . y C2 C3 S2 117.9(2) . . y C2 C3 Br2 125.8(2) . . y S2 C3 Br2 116.22(12) . . y C1 C4 S3 122.2(2) . . y C1 C4 S4 123.1(2) . . y S3 C4 S4 114.62(12) . . y C6 C5 S5 124.1(2) . . y C6 C5 S3 117.1(2) . . y S5 C5 S3 118.38(13) . . y C5 C6 S6 125.0(2) . . y C5 C6 S4 117.4(2) . . y S6 C6 S4 117.39(13) . . y C8 C7 S5 115.1(2) . . y C8 C7 H71 110.9(19) . . ? S5 C7 H71 102.5(18) . . ? C8 C7 H72 110.4(20) . . ? S5 C7 H72 110.1(20) . . ? H71 C7 H72 107.3(27) . . ? C9 C8 C7 113.1(2) . . y C9 C8 H81 107.3(20) . . ? C7 C8 H81 109.9(20) . . ? C9 C8 H82 106.2(27) . . ? C7 C8 H82 111.7(27) . . ? H81 C8 H82 108.4(32) . . ? N1 C9 C8 178.8(3) . . y C11 C10 S6 114.3(2) . . y C11 C10 H101 111.0(18) . . ? S6 C10 H101 109.1(17) . . ? C11 C10 H102 109.7(18) . . ? S6 C10 H102 102.7(18) . . ? H101 C10 H102 109.6(25) . . ? C12 C11 C10 112.2(2) . . y C12 C11 H111 109.9(20) . . ? C10 C11 H111 106.8(20) . . ? C12 C11 H112 107.8(22) . . ? C10 C11 H112 109.6(22) . . ? H111 C11 H112 110.6(29) . . ? N2 C12 C11 178.4(3) . . y 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 _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag C9 C8 C7 S5 62.3(3) . . . . y C8 C7 S5 C5 -77.6(2) . . . . y C7 S5 C5 C6 144.6(2) . . . . y S5 C5 C6 S6 -1.7(3) . . . . y C5 C6 S6 C10 -120.2(2) . . . . y C6 S6 C10 C11 73.1(2) . . . . y S6 C10 C11 C12 58.8(3) . . . . y _refine_diff_density_max .387 _refine_diff_density_min -.552 _refine_diff_density_rms .103 #==========================================END data_3.TCNQ _database_code_CSD 161759 _audit_creation_method SHELXL _chemical_name_systematic ; 4-iodo-5-methyl-4',5'-bis(methylsulfanyl)tetrathiafulvalene 7,7,8,8-tetracyanoquinodimethane ; _chemical_name_common ? _chemical_formula_moiety 'C9 H9 S6 I,C12 H4 N4' _chemical_formula_sum 'C21 H13 I N4 S6' _chemical_formula_weight 640.61 _chemical_melting_point ? _chemical_compound_source ? _ccdc_compound_id '3.TCNQ' _ccdc_biological_activity '?' _ccdc_polymorph '?' _ccdc_disorder ; The iodine atom and methyl group are disordered over two positions, I and I', C(9) and C(9'), respectively. ; _ccdc_comments '?' loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source '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' 'N' 'N' 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 'S' 'S' 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 'I' 'I' -0.4742 1.8119 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Triclinic _symmetry_space_group_name_H-M P-1 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 7.635(1) _cell_length_b 7.959(2) _cell_length_c 20.021(3) _cell_angle_alpha 81.20(1) _cell_angle_beta 88.64(1) _cell_angle_gamma 87.21(1) _cell_volume 1200.7(4) _cell_formula_units_Z 2 _cell_measurement_temperature 150(2) _cell_measurement_reflns_used 506 _cell_measurement_theta_min 12.0 _cell_measurement_theta_max 25.5 _exptl_crystal_description prism _exptl_crystal_colour black _exptl_crystal_size_max 0.40 _exptl_crystal_size_mid 0.16 _exptl_crystal_size_min 0.13 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.772 _exptl_crystal_density_method ? _exptl_crystal_F_000 632 _exptl_absorpt_coefficient_mu 1.874 _exptl_absorpt_correction_type integration _exptl_absorpt_correction_T_min 0.5932 _exptl_absorpt_correction_T_max 0.8095 _exptl_absorpt_process_details 'XPREP (SHELXTL,1997), R(int)=0.054 before correction' loop_ _exptl_crystal_face_index_h _exptl_crystal_face_index_k _exptl_crystal_face_index_l _exptl_crystal_face_perp_dist 0.00 0.00 -1.00 0.0650 0.00 0.00 1.00 0.0650 0.00 -1.00 -1.00 0.0800 0.00 1.00 1.00 0.0800 1.00 0.00 0.00 0.2000 -1.00 0.00 0.00 0.1900 -1.00 0.00 3.00 0.1200 _exptl_special_details ; The data collection nominally covered full sphere of reciprocal space, by a combination of 5 sets of \w scans; each set at different \f and/or 2\q angles and each scan (10 sec exposure) covering 0.3\% in \w. Crystal to detector distance 4.51 cm. Crystal decay was monitored by repeating 50 initial frames at the end of data collection and comparing 180 duplicate reflections. ; _diffrn_ambient_temperature 150(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device 'SMART 1K CCD area detector' _diffrn_measurement_method '\w scans' _diffrn_standards_number . _diffrn_standards_interval_count . _diffrn_standards_interval_time . _diffrn_standards_decay_% 0 _diffrn_reflns_number 13517 _diffrn_reflns_av_R_equivalents 0.0277 _diffrn_reflns_av_sigmaI/netI 0.0314 _diffrn_reflns_limit_h_min -10 _diffrn_reflns_limit_h_max 10 _diffrn_reflns_limit_k_min -11 _diffrn_reflns_limit_k_max 11 _diffrn_reflns_limit_l_min -26 _diffrn_reflns_limit_l_max 27 _diffrn_reflns_theta_min 2.06 _diffrn_reflns_theta_max 30.17 _reflns_number_total 6399 _reflns_number_observed 5505 _reflns_observed_criterion I>2\s(I) _computing_data_collection 'Siemens SMART' _computing_cell_refinement 'Siemens SMART' _computing_data_reduction 'Siemens SAINT' _computing_structure_solution 'SHELXS-86 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-93 (Sheldrick, 1993)' _computing_molecular_graphics SHELXTL _computing_publication_material SHELXTL _refine_special_details ; Refinement on F^2^ for ALL reflections except for 37 with very negative F^2^ or flagged by the user for potential systematic errors. Weighted R-factors wR and all goodnesses of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The observed criterion of F^2^ > 2sigma(F^2^) is used only for calculating _R_factor_obs etc. and is not relevant to the choice of reflections for refinement. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme 'calc w=1/[\s^2^(Fo^2^)+(0.0086P)^2^+1.8693P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens difmap _refine_ls_hydrogen_treatment refall _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 6362 _refine_ls_number_parameters 352 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0528 _refine_ls_R_factor_obs 0.0407 _refine_ls_wR_factor_all 0.0923 _refine_ls_wR_factor_obs 0.0801 _refine_ls_goodness_of_fit_all 1.242 _refine_ls_goodness_of_fit_obs 1.228 _refine_ls_restrained_S_all 1.307 _refine_ls_restrained_S_obs 1.228 _refine_ls_shift/esd_max -0.001 _refine_ls_shift/esd_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_thermal_displace_type _atom_site_occupancy _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_group I I 0.34337(6) 0.25477(7) 0.02064(2) 0.02760(12) Uani 0.5374(9) d P 1 I' I 0.36063(7) -0.11325(7) 0.12174(3) 0.02991(15) Uani 0.4626(9) d P 2 S1 S 0.51684(11) 0.41552(10) 0.14672(4) 0.0316(2) Uani 1 d . . S2 S 0.53526(10) 0.08357(9) 0.23606(4) 0.0280(2) Uani 1 d . . S3 S 0.67934(10) 0.59624(8) 0.26714(4) 0.02682(15) Uani 1 d . . S4 S 0.70660(9) 0.25986(8) 0.35385(3) 0.02344(14) Uani 1 d . . S5 S 0.77405(10) 0.78695(9) 0.37905(4) 0.0308(2) Uani 1 d . . S6 S 0.79421(13) 0.41567(10) 0.47792(4) 0.0396(2) Uani 1 d . . C11 C 0.5755(4) 0.3020(3) 0.22601(13) 0.0229(5) Uani 1 d . . C12 C 0.4365(4) 0.2396(5) 0.1156(2) 0.0338(7) Uani 1 d . . C13 C 0.4440(4) 0.0893(4) 0.1562(2) 0.0316(6) Uani 1 d . . C14 C 0.6442(3) 0.3771(3) 0.27533(13) 0.0221(5) Uani 1 d . . C15 C 0.7388(4) 0.5918(3) 0.35191(14) 0.0242(5) Uani 1 d . . C16 C 0.7496(3) 0.4388(3) 0.39157(14) 0.0230(5) Uani 1 d . . C9' C 0.3653(11) 0.3074(11) 0.0405(5) 0.033(2) Uani 0.4626(9) d P 2 H91' H 0.4643(15) 0.3401(95) 0.0096(10) 0.098(27) Uiso 0.4626(9) d PR 2 H92' H 0.2861(82) 0.4082(61) 0.0423(9) 0.098(27) Uiso 0.4626(9) d PR 2 H93' H 0.3012(90) 0.2193(37) 0.0230(17) 0.098(27) Uiso 0.4626(9) d PR 2 C9 C 0.3870(10) -0.0977(9) 0.1474(4) 0.0266(15) Uani 0.5374(9) d P 1 H91 H 0.3239(73) -0.1495(33) 0.1881(13) 0.087(20) Uiso 0.5374(9) d PR 1 H92 H 0.4923(12) -0.1689(25) 0.1400(32) 0.087(20) Uiso 0.5374(9) d PR 1 H93 H 0.3102(68) -0.0901(12) 0.1082(20) 0.087(20) Uiso 0.5374(9) d PR 1 C17 C 0.5594(4) 0.8290(4) 0.4152(2) 0.0323(6) Uani 1 d . . H171 H 0.5685(51) 0.9312(50) 0.4322(20) 0.047(11) Uiso 1 d . . H172 H 0.5389(48) 0.7477(49) 0.4523(19) 0.041(10) Uiso 1 d . . H173 H 0.4727(54) 0.8427(50) 0.3789(21) 0.052(12) Uiso 1 d . . C18 C 0.8468(5) 0.1909(5) 0.4994(2) 0.0396(8) Uani 1 d . . H181 H 0.8654(50) 0.1768(47) 0.5483(21) 0.045(10) Uiso 1 d . . H182 H 0.9358(53) 0.1570(48) 0.4739(20) 0.044(11) Uiso 1 d . . H183 H 0.7481(55) 0.1237(50) 0.4921(20) 0.049(11) Uiso 1 d . . C1 C 0.9662(3) 0.1961(3) 0.15305(14) 0.0226(5) Uani 1 d . . C2 C 1.0126(4) 0.0900(3) 0.21616(14) 0.0235(5) Uani 1 d . . H2 H 0.9973(43) -0.0338(42) 0.2239(16) 0.029(8) Uiso 1 d . . C3 C 1.0840(4) 0.1567(3) 0.26665(14) 0.0233(5) Uani 1 d . . H3 H 1.1120(43) 0.0912(41) 0.3075(17) 0.028(8) Uiso 1 d . . C4 C 1.1112(3) 0.3373(3) 0.26024(14) 0.0219(5) Uani 1 d . . C5 C 1.0635(4) 0.4432(3) 0.19760(14) 0.0242(5) Uani 1 d . . H5 H 1.0924(44) 0.5577(43) 0.1921(17) 0.031(9) Uiso 1 d . . C6 C 0.9944(4) 0.3765(3) 0.14612(14) 0.0247(5) Uani 1 d . . H6 H 0.9621(40) 0.4581(38) 0.1060(16) 0.022(8) Uiso 1 d . . C7 C 0.8975(4) 0.1256(4) 0.10073(14) 0.0253(5) Uani 1 d . . C8 C 1.1790(4) 0.4045(3) 0.31371(14) 0.0239(5) Uani 1 d . . C71 C 0.8563(4) 0.2250(4) 0.03676(15) 0.0309(6) Uani 1 d . . C72 C 0.8671(4) -0.0524(4) 0.1071(2) 0.0301(6) Uani 1 d . . C81 C 1.1945(4) 0.5855(4) 0.31116(15) 0.0282(6) Uani 1 d . . C82 C 1.2322(4) 0.2987(4) 0.37482(15) 0.0275(6) Uani 1 d . . N71 N 0.8248(4) 0.3023(4) -0.01579(15) 0.0442(7) Uani 1 d . . N81 N 1.2050(4) 0.7295(3) 0.31078(15) 0.0383(6) Uani 1 d . . N82 N 1.2761(4) 0.2111(4) 0.42320(14) 0.0395(6) Uani 1 d . . N72 N 0.8419(4) -0.1956(4) 0.1113(2) 0.0400(6) Uani 1 d . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 I 0.0270(2) 0.0369(3) 0.0181(2) -0.0015(2) -0.00360(14) -0.0010(2) I' 0.0268(2) 0.0263(2) 0.0402(4) -0.0158(2) -0.0047(2) -0.0013(2) S1 0.0354(4) 0.0338(4) 0.0246(3) -0.0008(3) -0.0056(3) -0.0014(3) S2 0.0324(4) 0.0236(3) 0.0294(3) -0.0074(3) -0.0059(3) -0.0038(3) S3 0.0351(4) 0.0194(3) 0.0256(3) -0.0015(2) -0.0009(3) -0.0034(3) S4 0.0288(3) 0.0184(3) 0.0236(3) -0.0035(2) -0.0037(3) -0.0036(2) S5 0.0309(4) 0.0224(3) 0.0417(4) -0.0113(3) -0.0006(3) -0.0076(3) S6 0.0586(5) 0.0327(4) 0.0295(4) -0.0069(3) -0.0165(4) -0.0072(4) C11 0.0245(13) 0.0245(13) 0.0202(12) -0.0043(10) -0.0034(10) -0.0014(10) C12 0.0233(14) 0.056(2) 0.0265(14) -0.0181(14) -0.0029(11) -0.0018(13) C13 0.0217(13) 0.045(2) 0.033(2) -0.0213(13) -0.0016(11) -0.0024(12) C14 0.0226(12) 0.0190(12) 0.0249(13) -0.0030(10) -0.0023(10) -0.0016(9) C15 0.0239(13) 0.0201(12) 0.0299(14) -0.0069(10) -0.0011(10) -0.0042(10) C16 0.0225(12) 0.0220(12) 0.0259(13) -0.0072(10) -0.0029(10) -0.0030(10) C9' 0.036(4) 0.032(4) 0.032(4) -0.010(3) 0.005(3) -0.005(3) C9 0.031(3) 0.027(3) 0.023(3) -0.005(3) -0.001(3) -0.005(2) C17 0.037(2) 0.0262(15) 0.035(2) -0.0098(13) 0.0020(13) -0.0019(12) C18 0.044(2) 0.041(2) 0.030(2) 0.0016(14) -0.0056(15) 0.008(2) C1 0.0184(12) 0.0253(13) 0.0245(13) -0.0056(10) 0.0023(10) 0.0006(10) C2 0.0244(13) 0.0200(12) 0.0257(13) -0.0033(10) 0.0004(10) 0.0017(10) C3 0.0257(13) 0.0187(12) 0.0249(13) -0.0019(10) 0.0002(10) 0.0003(10) C4 0.0188(12) 0.0214(12) 0.0255(13) -0.0044(10) 0.0020(10) -0.0007(9) C5 0.0250(13) 0.0187(12) 0.0279(14) -0.0006(10) 0.0009(10) -0.0017(10) C6 0.0274(13) 0.0226(13) 0.0229(13) -0.0003(10) 0.0011(10) 0.0003(10) C7 0.0209(12) 0.0308(14) 0.0253(13) -0.0083(11) 0.0011(10) 0.0008(10) C8 0.0219(12) 0.0243(13) 0.0258(13) -0.0051(10) 0.0016(10) -0.0012(10) C71 0.0275(14) 0.042(2) 0.0242(14) -0.0092(12) -0.0025(11) 0.0005(12) C72 0.0265(14) 0.038(2) 0.0286(14) -0.0127(12) -0.0033(11) 0.0003(12) C81 0.0262(14) 0.0311(15) 0.0280(14) -0.0053(11) -0.0036(11) -0.0034(11) C82 0.0293(14) 0.0249(13) 0.0298(14) -0.0088(11) -0.0005(11) -0.0017(11) N71 0.043(2) 0.057(2) 0.0332(15) -0.0067(13) -0.0061(12) 0.0001(14) N81 0.046(2) 0.0269(13) 0.043(2) -0.0068(11) -0.0066(13) -0.0056(11) N82 0.048(2) 0.0357(14) 0.0347(15) -0.0052(12) -0.0088(12) 0.0039(12) N72 0.042(2) 0.038(2) 0.043(2) -0.0166(13) -0.0020(13) -0.0048(12) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag I C12 2.029(3) . ? I' C13 1.985(3) . ? S1 C11 1.759(3) . ? S1 C12 1.759(3) . ? S2 C13 1.753(3) . ? S2 C11 1.761(3) . ? S3 C14 1.760(3) . ? S3 C15 1.762(3) . ? S4 C16 1.759(3) . ? S4 C14 1.764(3) . ? S5 C15 1.757(3) . ? S5 C17 1.812(3) . ? S6 C16 1.750(3) . ? S6 C18 1.803(4) . ? C11 C14 1.357(4) . ? C12 C13 1.339(5) . ? C12 C9' 1.615(10) . ? C13 C9 1.606(8) . ? C15 C16 1.348(4) . ? C17 H171 0.93(4) . ? C17 H172 0.92(4) . ? C17 H173 0.98(4) . ? C18 H181 0.98(4) . ? C18 H182 0.90(4) . ? C18 H183 0.97(4) . ? C1 C7 1.386(4) . ? C1 C6 1.447(4) . ? C1 C2 1.450(4) . ? C2 C3 1.349(4) . ? C2 H2 0.99(3) . ? C3 C4 1.448(4) . ? C3 H3 0.92(3) . ? C4 C8 1.389(4) . ? C4 C5 1.444(4) . ? C5 C6 1.358(4) . ? C5 H5 0.94(3) . ? C6 H6 0.98(3) . ? C7 C71 1.432(4) . ? C7 C72 1.433(4) . ? C8 C82 1.430(4) . ? C8 C81 1.444(4) . ? C71 N71 1.159(4) . ? C72 N72 1.155(4) . ? C81 N81 1.152(4) . ? C82 N82 1.150(4) . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C11 S1 C12 95.33(14) . . ? C13 S2 C11 95.71(14) . . ? C14 S3 C15 95.23(12) . . ? C16 S4 C14 95.33(13) . . ? C15 S5 C17 99.69(14) . . ? C16 S6 C18 103.0(2) . . ? C14 C11 S1 122.8(2) . . ? C14 C11 S2 123.1(2) . . ? S1 C11 S2 114.18(14) . . ? C13 C12 C9' 135.2(4) . . ? C13 C12 S1 117.6(2) . . ? C9' C12 S1 107.1(4) . . ? C13 C12 I 119.6(2) . . ? S1 C12 I 122.8(2) . . ? C12 C13 C9 133.2(4) . . ? C12 C13 S2 117.1(2) . . ? C9 C13 S2 109.7(3) . . ? C12 C13 I' 118.7(2) . . ? S2 C13 I' 124.1(2) . . ? C11 C14 S3 123.7(2) . . ? C11 C14 S4 122.0(2) . . ? S3 C14 S4 114.31(15) . . ? C16 C15 S5 124.9(2) . . ? C16 C15 S3 117.4(2) . . ? S5 C15 S3 117.7(2) . . ? C15 C16 S6 122.6(2) . . ? C15 C16 S4 117.1(2) . . ? S6 C16 S4 120.2(2) . . ? S5 C17 H171 104.9(24) . . ? S5 C17 H172 109.6(23) . . ? H171 C17 H172 105.7(32) . . ? S5 C17 H173 108.6(24) . . ? H171 C17 H173 110.4(33) . . ? H172 C17 H173 116.9(33) . . ? S6 C18 H181 103.1(22) . . ? S6 C18 H182 111.6(24) . . ? H181 C18 H182 116.8(33) . . ? S6 C18 H183 111.5(24) . . ? H181 C18 H183 107.5(32) . . ? H182 C18 H183 106.4(34) . . ? C7 C1 C6 121.1(3) . . ? C7 C1 C2 120.5(2) . . ? C6 C1 C2 118.3(2) . . ? C3 C2 C1 120.9(2) . . ? C3 C2 H2 116.8(19) . . ? C1 C2 H2 122.2(19) . . ? C2 C3 C4 121.0(3) . . ? C2 C3 H3 122.0(20) . . ? C4 C3 H3 117.0(20) . . ? C8 C4 C5 121.8(2) . . ? C8 C4 C3 120.1(2) . . ? C5 C4 C3 118.0(2) . . ? C6 C5 C4 121.3(2) . . ? C6 C5 H5 121.0(21) . . ? C4 C5 H5 117.4(21) . . ? C5 C6 C1 120.4(2) . . ? C5 C6 H6 115.9(18) . . ? C1 C6 H6 123.7(18) . . ? C1 C7 C71 122.2(3) . . ? C1 C7 C72 121.8(3) . . ? C71 C7 C72 116.0(3) . . ? C4 C8 C82 121.8(2) . . ? C4 C8 C81 121.6(3) . . ? C82 C8 C81 116.6(2) . . ? N71 C71 C7 178.3(3) . . ? N72 C72 C7 179.1(3) . . ? N81 C81 C8 178.2(3) . . ? N82 C82 C8 178.6(3) . . ? 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 _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag C17 S5 C15 C16 -82.9(3) . . . . ? S5 C15 C16 S6 2.2(4) . . . . ? C15 C16 S6 C18 -166.2(3) . . . . ? _refine_diff_density_max 0.475 _refine_diff_density_min -0.406 _refine_diff_density_rms 0.080 #=======================================END data_4.TCNQ _database_code_CSD 161760 _audit_creation_method SHELXL _chemical_name_systematic ; 4-iodo-4',5'-bis(methylsulfanyl)tetrathiafulvalene 7,7,8,8-tetracyanoquinodimethane ; _chemical_name_common ? _chemical_formula_moiety 'C12 H4 N4,C8 H7 S6 I' _chemical_formula_sum 'C20 H11 I N4 S6' _chemical_formula_weight 626.59 _chemical_melting_point ? _chemical_compound_source ? _ccdc_compound_id '4.TCNQ' _ccdc_biological_activity '?' _ccdc_polymorph '?' _ccdc_disorder ; The I atom is disordered over two positions, refined with occupancies 97% (I) and 3% (I'). For the corresponding hydrogen, only the major position, H(13), was refined. ; _ccdc_comments '?' loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source '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' 'N' 'N' 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 'S' 'S' 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 'I' 'I' -0.4742 1.8119 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting triclinic _symmetry_space_group_name_H-M P-1 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 7.969(1) _cell_length_b 9.066(1) _cell_length_c 17.482(1) _cell_angle_alpha 81.02(1) _cell_angle_beta 83.25(1) _cell_angle_gamma 77.12(1) _cell_volume 1211.7(2) _cell_formula_units_Z 2 _cell_measurement_temperature 295(2) _cell_measurement_reflns_used 491 _cell_measurement_theta_min 12.0 _cell_measurement_theta_max 24.0 _exptl_crystal_description plate _exptl_crystal_colour black _exptl_crystal_size_max 0.3 _exptl_crystal_size_mid 0.2 _exptl_crystal_size_min 0.1 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.717 _exptl_crystal_density_method ? _exptl_crystal_F_000 616 _exptl_absorpt_coefficient_mu 1.855 _exptl_absorpt_correction_type 'multi-scan' _exptl_absorpt_correction_T_min 0.3452 _exptl_absorpt_correction_T_max 0.9333 _exptl_absorpt_process_details 'integration then SADABS (Sheldrick,1996),R(int)=0.067 before correction' loop_ _exptl_crystal_face_index_h _exptl_crystal_face_index_k _exptl_crystal_face_index_l _exptl_crystal_face_perp_dist 0.00 0.00 -1.00 0.0500 0.00 0.00 1.00 0.0500 0.00 1.00 -1.00 0.1000 0.00 -1.00 1.00 0.1000 1.00 0.00 -1.00 0.1000 -1.00 0.00 1.00 0.1000 _exptl_special_details ; The data collection nominally covered full sphere of reciprocal space, by a combination of 5 sets of \w scans; each set at different \f and/or 2\q angles and each scan (10 sec exposure) covering 0.3\% in \w. Crystal to detector distance 4.51 cm. Crystal decay was monitored by repeating 50 initial frames at the end of data collection and comparing 121 duplicate reflections. ; _diffrn_ambient_temperature 295(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device 'SMART 1K CCD area detector' _diffrn_measurement_method '\w scans' _diffrn_standards_number . _diffrn_standards_interval_count . _diffrn_standards_interval_time . _diffrn_standards_decay_% 0 _diffrn_reflns_number 14342 _diffrn_reflns_av_R_equivalents 0.0355 _diffrn_reflns_av_sigmaI/netI 0.0554 _diffrn_reflns_limit_h_min -11 _diffrn_reflns_limit_h_max 11 _diffrn_reflns_limit_k_min -12 _diffrn_reflns_limit_k_max 12 _diffrn_reflns_limit_l_min -23 _diffrn_reflns_limit_l_max 24 _diffrn_reflns_theta_min 2.33 _diffrn_reflns_theta_max 30.53 _reflns_number_total 6471 _reflns_number_observed 4372 _reflns_observed_criterion I>2\s(I) _computing_data_collection 'Siemens SMART' _computing_cell_refinement 'Siemens SMART' _computing_data_reduction 'Siemens SAINT' _computing_structure_solution 'SHELXS-86 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-93 (Sheldrick, 1993)' _computing_molecular_graphics 'Siemens SHELXTL' _computing_publication_material 'Siemens SHELXTL' _refine_special_details ; Refinement on F^2^ for ALL reflections except for 16 with very negative F^2^ or flagged by the user for potential systematic errors. Weighted R-factors wR and all goodnesses of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The observed criterion of F^2^ > 2sigma(F^2^) is used only for calculating _R_factor_obs etc. and is not relevant to the choice of reflections for refinement. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme 'calc w=1/[\s^2^(Fo^2^)+(0.0235P)^2^+0.6613P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens difmap _refine_ls_hydrogen_treatment refall _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 6455 _refine_ls_number_parameters 328 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0777 _refine_ls_R_factor_obs 0.0412 _refine_ls_wR_factor_all 0.0939 _refine_ls_wR_factor_obs 0.0761 _refine_ls_goodness_of_fit_all 1.077 _refine_ls_goodness_of_fit_obs 1.093 _refine_ls_restrained_S_all 1.096 _refine_ls_restrained_S_obs 1.093 _refine_ls_shift/esd_max -0.002 _refine_ls_shift/esd_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_thermal_displace_type _atom_site_occupancy _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_group I I 0.69557(3) 0.65074(3) 0.40740(2) 0.05459(10) Uani 0.97 d P 1 I' I 0.4012(14) 0.7227(12) 0.4904(6) 0.069(3) Uiso 0.03 d P 2 S1 S 0.51248(11) 0.46562(12) 0.30656(6) 0.0524(3) Uani 1 d . . S2 S 0.15859(11) 0.55972(11) 0.37934(5) 0.0460(2) Uani 1 d . . S3 S 0.36701(11) 0.28382(12) 0.19120(6) 0.0494(2) Uani 1 d . . S4 S 0.01178(11) 0.38790(11) 0.25823(5) 0.0466(2) Uani 1 d . . S5 S 0.24897(14) 0.16541(13) 0.05781(6) 0.0601(3) Uani 1 d . . S6 S -0.14861(13) 0.27626(12) 0.13630(6) 0.0549(3) Uani 1 d . . C1 C 0.1949(4) 0.0173(4) 0.3397(2) 0.0392(8) Uani 1 d . . C2 C 0.0133(4) 0.0254(4) 0.3371(2) 0.0406(8) Uani 1 d . . H2 H -0.0637(45) 0.0688(40) 0.3732(21) 0.047(10) Uiso 1 d . . C3 C -0.0447(4) -0.0370(4) 0.2826(2) 0.0414(8) Uani 1 d . . H3 H -0.1737(44) -0.0252(38) 0.2806(19) 0.042(9) Uiso 1 d . . C4 C 0.0732(4) -0.1159(4) 0.2263(2) 0.0396(8) Uani 1 d . . C5 C 0.2543(4) -0.1251(4) 0.2293(2) 0.0426(8) Uani 1 d . . H5 H 0.3298(45) -0.1664(39) 0.1929(21) 0.045(10) Uiso 1 d . . C6 C 0.3132(5) -0.0618(4) 0.2829(2) 0.0428(8) Uani 1 d . . H6 H 0.4329(43) -0.0712(36) 0.2830(18) 0.035(9) Uiso 1 d . . C7 C 0.2531(4) 0.0842(4) 0.3946(2) 0.0417(8) Uani 1 d . . C8 C 0.0132(5) -0.1818(4) 0.1710(2) 0.0465(9) Uani 1 d . . C11 C 0.2923(4) 0.4602(4) 0.3089(2) 0.0421(8) Uani 1 d . . C12 C 0.4806(4) 0.5844(4) 0.3792(2) 0.0412(8) Uani 1 d . . C13 C 0.3218(5) 0.6262(4) 0.4118(2) 0.0444(8) Uani 1 d . . H13 H 0.2775(50) 0.6853(45) 0.4534(23) 0.058(12) Uiso 0.97 d P 1 C14 C 0.2309(4) 0.3877(4) 0.2593(2) 0.0410(8) Uani 1 d . . C15 C 0.2000(5) 0.2571(4) 0.1410(2) 0.0423(8) Uani 1 d . . C16 C 0.0365(4) 0.3035(4) 0.1722(2) 0.0425(8) Uani 1 d . . C17 C 0.4624(7) 0.1957(7) 0.0252(3) 0.0675(13) Uani 1 d . . H171 H 0.5514(56) 0.1326(49) 0.0571(24) 0.063(13) Uiso 1 d . . H172 H 0.4895(55) 0.1679(50) -0.0204(27) 0.071(14) Uiso 1 d . . H173 H 0.4666(56) 0.3024(56) 0.0203(25) 0.074(15) Uiso 1 d . . C18 C -0.2406(7) 0.4678(6) 0.0961(3) 0.0655(12) Uani 1 d . . H181 H -0.3409(63) 0.4682(54) 0.0651(27) 0.090(15) Uiso 1 d . . H182 H -0.1609(58) 0.5010(52) 0.0591(27) 0.071(15) Uiso 1 d . . H183 H -0.2737(64) 0.5419(60) 0.1348(30) 0.102(18) Uiso 1 d . . C71 C 0.4326(5) 0.0852(5) 0.3976(2) 0.0508(9) Uani 1 d . . C72 C 0.1358(5) 0.1596(4) 0.4516(2) 0.0472(9) Uani 1 d . . C81 C 0.1275(5) -0.2705(5) 0.1181(2) 0.0576(10) Uani 1 d . . C82 C -0.1688(5) -0.1671(5) 0.1654(2) 0.0571(10) Uani 1 d . . N71 N 0.5747(4) 0.0883(5) 0.4002(2) 0.0719(11) Uani 1 d . . N72 N 0.0392(4) 0.2202(4) 0.4963(2) 0.0640(10) Uani 1 d . . N81 N 0.2229(5) -0.3447(5) 0.0778(2) 0.0821(12) Uani 1 d . . N82 N -0.3134(5) -0.1541(5) 0.1610(2) 0.0810(12) Uani 1 d . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 I 0.04096(14) 0.0697(2) 0.0639(2) -0.02052(14) -0.01082(11) -0.02299(13) S1 0.0349(4) 0.0688(6) 0.0635(6) -0.0343(5) 0.0014(4) -0.0170(4) S2 0.0351(4) 0.0569(6) 0.0518(5) -0.0218(5) -0.0004(4) -0.0135(4) S3 0.0385(5) 0.0634(6) 0.0544(6) -0.0268(5) -0.0002(4) -0.0163(4) S4 0.0373(4) 0.0587(6) 0.0507(5) -0.0218(5) -0.0047(4) -0.0145(4) S5 0.0694(7) 0.0730(7) 0.0491(6) -0.0285(5) 0.0022(5) -0.0281(6) S6 0.0520(5) 0.0543(6) 0.0679(7) -0.0134(5) -0.0233(5) -0.0180(5) C1 0.040(2) 0.044(2) 0.035(2) -0.007(2) -0.0014(14) -0.011(2) C2 0.038(2) 0.047(2) 0.040(2) -0.012(2) 0.0059(15) -0.017(2) C3 0.034(2) 0.049(2) 0.044(2) -0.013(2) 0.0020(15) -0.013(2) C4 0.044(2) 0.042(2) 0.036(2) -0.0078(15) -0.0001(14) -0.014(2) C5 0.037(2) 0.051(2) 0.041(2) -0.014(2) 0.002(2) -0.011(2) C6 0.036(2) 0.051(2) 0.043(2) -0.009(2) -0.0015(15) -0.009(2) C7 0.036(2) 0.048(2) 0.043(2) -0.012(2) -0.0016(15) -0.009(2) C8 0.050(2) 0.054(2) 0.040(2) -0.013(2) 0.000(2) -0.017(2) C11 0.037(2) 0.048(2) 0.047(2) -0.017(2) -0.0030(15) -0.013(2) C12 0.040(2) 0.047(2) 0.044(2) -0.015(2) -0.0080(15) -0.015(2) C13 0.043(2) 0.052(2) 0.044(2) -0.019(2) -0.003(2) -0.015(2) C14 0.035(2) 0.048(2) 0.045(2) -0.016(2) -0.0041(14) -0.012(2) C15 0.052(2) 0.042(2) 0.037(2) -0.008(2) -0.006(2) -0.017(2) C16 0.044(2) 0.042(2) 0.047(2) -0.012(2) -0.009(2) -0.014(2) C17 0.060(3) 0.085(4) 0.059(3) -0.027(3) 0.006(2) -0.015(3) C18 0.069(3) 0.065(3) 0.067(3) -0.007(3) -0.025(3) -0.013(3) C71 0.046(2) 0.058(2) 0.052(2) -0.019(2) -0.005(2) -0.008(2) C72 0.044(2) 0.060(2) 0.044(2) -0.015(2) -0.006(2) -0.018(2) C81 0.063(2) 0.071(3) 0.048(2) -0.020(2) -0.001(2) -0.025(2) C82 0.058(2) 0.070(3) 0.053(2) -0.026(2) -0.003(2) -0.023(2) N71 0.045(2) 0.084(3) 0.089(3) -0.018(2) -0.012(2) -0.013(2) N72 0.052(2) 0.087(3) 0.061(2) -0.038(2) 0.003(2) -0.016(2) N81 0.084(3) 0.102(3) 0.069(3) -0.043(2) 0.014(2) -0.027(2) N82 0.057(2) 0.115(3) 0.087(3) -0.048(3) -0.004(2) -0.027(2) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag I C12 2.071(3) . ? I' C13 1.970(11) . ? I' C12 2.422(11) . ? I' H13 1.37(4) . ? S1 C12 1.751(3) . ? S1 C11 1.762(3) . ? S2 C13 1.734(3) . ? S2 C11 1.754(3) . ? S3 C14 1.753(3) . ? S3 C15 1.757(3) . ? S4 C14 1.748(3) . ? S4 C16 1.762(3) . ? S5 C15 1.748(3) . ? S5 C17 1.796(5) . ? S6 C16 1.749(3) . ? S6 C18 1.794(5) . ? C1 C7 1.385(4) . ? C1 C2 1.438(5) . ? C1 C6 1.445(5) . ? C2 C3 1.352(5) . ? C2 H2 0.90(4) . ? C3 C4 1.437(5) . ? C3 H3 1.01(3) . ? C4 C8 1.393(4) . ? C4 C5 1.434(5) . ? C5 C6 1.349(5) . ? C5 H5 0.89(3) . ? C6 H6 0.94(3) . ? C7 C72 1.429(5) . ? C7 C71 1.440(5) . ? C8 C81 1.428(5) . ? C8 C82 1.440(5) . ? C11 C14 1.358(4) . ? C12 C13 1.324(5) . ? C13 H13 0.96(4) . ? C15 C16 1.354(5) . ? C17 H171 0.98(4) . ? C17 H172 0.86(4) . ? C17 H173 0.97(5) . ? C18 H181 1.02(5) . ? C18 H182 0.92(5) . ? C18 H183 1.00(5) . ? C71 N71 1.145(5) . ? C72 N72 1.145(4) . ? C81 N81 1.149(5) . ? C82 N82 1.142(5) . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C13 I' C12 33.1(2) . . ? C13 I' H13 26.3(16) . . ? C12 I' H13 59.3(17) . . ? C12 S1 C11 94.5(2) . . ? C13 S2 C11 95.4(2) . . ? C14 S3 C15 95.6(2) . . ? C14 S4 C16 95.4(2) . . ? C15 S5 C17 102.3(2) . . ? C16 S6 C18 100.9(2) . . ? C7 C1 C2 120.8(3) . . ? C7 C1 C6 121.5(3) . . ? C2 C1 C6 117.8(3) . . ? C3 C2 C1 121.1(3) . . ? C3 C2 H2 118.7(22) . . ? C1 C2 H2 120.2(22) . . ? C2 C3 C4 121.1(3) . . ? C2 C3 H3 119.3(19) . . ? C4 C3 H3 119.6(19) . . ? C8 C4 C5 121.1(3) . . ? C8 C4 C3 121.0(3) . . ? C5 C4 C3 117.9(3) . . ? C6 C5 C4 121.4(3) . . ? C6 C5 H5 118.5(23) . . ? C4 C5 H5 119.9(23) . . ? C5 C6 C1 120.8(3) . . ? C5 C6 H6 118.6(19) . . ? C1 C6 H6 120.6(19) . . ? C1 C7 C72 121.3(3) . . ? C1 C7 C71 123.0(3) . . ? C72 C7 C71 115.7(3) . . ? C4 C8 C81 122.2(3) . . ? C4 C8 C82 121.5(3) . . ? C81 C8 C82 116.3(3) . . ? C14 C11 S2 122.8(3) . . ? C14 C11 S1 122.8(3) . . ? S2 C11 S1 114.3(2) . . ? C13 C12 S1 118.1(3) . . ? C13 C12 I 124.7(2) . . ? S1 C12 I 117.2(2) . . ? C13 C12 I' 54.3(3) . . ? S1 C12 I' 170.1(3) . . ? C12 C13 S2 117.6(3) . . ? C12 C13 I' 92.6(4) . . ? S2 C13 I' 149.0(4) . . ? C12 C13 H13 131.6(24) . . ? S2 C13 H13 110.7(24) . . ? C11 C14 S4 123.4(3) . . ? C11 C14 S3 122.3(3) . . ? S4 C14 S3 114.3(2) . . ? C16 C15 S5 123.1(3) . . ? C16 C15 S3 116.7(3) . . ? S5 C15 S3 120.1(2) . . ? C15 C16 S6 124.6(3) . . ? C15 C16 S4 116.9(3) . . ? S6 C16 S4 118.3(2) . . ? S5 C17 H171 113.5(25) . . ? S5 C17 H172 108.2(30) . . ? H171 C17 H172 105.0(37) . . ? S5 C17 H173 111.3(27) . . ? H171 C17 H173 111.3(37) . . ? H172 C17 H173 107.1(40) . . ? S6 C18 H181 110.1(27) . . ? S6 C18 H182 107.8(29) . . ? H181 C18 H182 103.2(38) . . ? S6 C18 H183 114.6(30) . . ? H181 C18 H183 111.7(39) . . ? H182 C18 H183 108.6(42) . . ? N71 C71 C7 178.9(4) . . ? N72 C72 C7 178.6(4) . . ? N81 C81 C8 177.5(5) . . ? N82 C82 C8 179.4(5) . . ? _refine_diff_density_max 0.589 _refine_diff_density_min -0.589 _refine_diff_density_rms 0.079 #=====================================END data_5.I4 _database_code_CSD 161761 _audit_creation_method SHELXL _chemical_name_systematic ; 4-iodo-4',5,5'-trimethyltetrathiafulvalenium triiodide hemi(diiodine) ; _chemical_name_common ? _chemical_formula_moiety 'C9 H9 S4 1+,I3 1-,0.5(I2)' _chemical_formula_sum 'C9 H9 I5 S4' _chemical_formula_weight 879.90 _chemical_melting_point ? _chemical_compound_source ? _ccdc_compound_id '5.I4' _ccdc_biological_activity '?' _ccdc_polymorph '?' _ccdc_disorder ; Iodo-substituent at TTF is distributed between 4 positions, I(11), I(12), I(13), I(14) with the probabilities 25%, 25%, 35%, 15% respectively, i.e. I is mixed with Me-substituents. ; _ccdc_comments '?' loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source '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' 'S' 'S' 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 'I' 'I' -0.4742 1.8119 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting 'Monoclinic' _symmetry_space_group_name_H-M 'P2(1)/n ' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, y+1/2, -z+1/2' '-x, -y, -z' 'x-1/2, -y-1/2, z-1/2' _cell_length_a 14.034(1) _cell_length_b 8.077(1) _cell_length_c 17.960(1) _cell_angle_alpha 90.00 _cell_angle_beta 107.20(1) _cell_angle_gamma 90.00 _cell_volume 1944.8(3) _cell_formula_units_Z 4 _cell_measurement_temperature 150(2) _cell_measurement_reflns_used 417 _cell_measurement_theta_min 12.0 _cell_measurement_theta_max 21.9 _exptl_crystal_description 'plate ' _exptl_crystal_colour 'black ' _exptl_crystal_size_max 0.44 _exptl_crystal_size_mid 0.17 _exptl_crystal_size_min 0.008 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 3.005 _exptl_crystal_density_method ? _exptl_crystal_F_000 1568 _exptl_absorpt_coefficient_mu 8.410 _exptl_absorpt_correction_type 'integration' _exptl_absorpt_correction_T_min 0.1241 _exptl_absorpt_correction_T_max 0.9329 _exptl_absorpt_process_details 'XPREP (SHELXTL,1997), R(int)=0.184 before correction' loop_ _exptl_crystal_face_index_h _exptl_crystal_face_index_k _exptl_crystal_face_index_l _exptl_crystal_face_perp_dist -1.00 0.00 1.00 0.0040 1.00 0.00 -1.00 0.0040 0.00 0.00 1.00 0.0850 0.00 0.00 -1.00 0.0850 0.00 -1.00 -1.00 0.1500 0.00 1.00 0.00 0.2200 -1.00 4.00 -3.00 0.1900 _exptl_special_details ; The data collection nominally covered over a hemisphere of reciprocal space, by a combination of 4 sets of \w scans; each set at different \f and/or 2\q angles and each scan (30 sec exposure) covering 0.3\% in \w. Crystal to detector distance 4.51 cm. Crystal decay was monitored by repeating 50 initial frames at the end of data collection and comparing 142 duplicate reflections. ; _diffrn_ambient_temperature 150(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device 'SMART 1K CCD area detector' _diffrn_measurement_method '\w scans' _diffrn_standards_number . _diffrn_standards_interval_count . _diffrn_standards_interval_time . _diffrn_standards_decay_% 0 _diffrn_reflns_number 13637 _diffrn_reflns_av_R_equivalents 0.1516 _diffrn_reflns_av_sigmaI/netI 0.0995 _diffrn_reflns_limit_h_min -14 _diffrn_reflns_limit_h_max 18 _diffrn_reflns_limit_k_min -10 _diffrn_reflns_limit_k_max 10 _diffrn_reflns_limit_l_min -23 _diffrn_reflns_limit_l_max 23 _diffrn_reflns_theta_min 1.6 _diffrn_reflns_theta_max 27.5 _reflns_number_total 4458 _reflns_number_observed 3068 _reflns_observed_criterion >2sigma(I) _computing_data_collection 'Siemens SMART' _computing_cell_refinement 'Siemens SMART' _computing_data_reduction 'Siemens SAINT' _computing_structure_solution 'SHELXS-86 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-93 (Sheldrick, 1993)' _computing_molecular_graphics 'Siemens SHELXTL' _computing_publication_material 'Siemens SHELXTL' _refine_special_details ; Refinement on F^2^ for ALL reflections except for 150 with very negative F^2^ . Weighted R-factors wR and all goodnesses of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The observed criterion of F^2^ > 2sigma(F^2^) is used only for calculating _R_factor_obs etc. and is not relevant to the choice of reflections for refinement. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme 'calc w=1/[\s^2^(Fo^2^)+(0.0430P)^2^+35.2117P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment constr _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 4308 _refine_ls_number_parameters 179 _refine_ls_number_restraints 4 _refine_ls_R_factor_all 0.1174 _refine_ls_R_factor_obs 0.0766 _refine_ls_wR_factor_all 0.2244 _refine_ls_wR_factor_obs 0.1772 _refine_ls_goodness_of_fit_all 1.177 _refine_ls_goodness_of_fit_obs 1.248 _refine_ls_restrained_S_all 1.308 _refine_ls_restrained_S_obs 1.247 _refine_ls_shift/esd_max -0.014 _refine_ls_shift/esd_mean 0.001 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_thermal_displace_type _atom_site_occupancy _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_group I1 I 0.23214(9) 0.50760(14) 0.35672(6) 0.0557(3) Uani 1 d . . I2 I 0.39130(9) 0.41333(12) 0.29919(5) 0.0483(3) Uani 1 d . . I3 I 0.55996(11) 0.3082(2) 0.23478(6) 0.0653(4) Uani 1 d . . I4 I 0.50424(9) 0.0855(2) 0.06831(7) 0.0673(4) Uani 1 d . . I12 I 0.2581(4) 0.3977(6) 0.5942(3) 0.0562(11) Uani 0.25 d P 1 I13 I 0.3649(11) 0.1816(9) 0.7423(5) 0.120(4) Uani 0.25 d P 1 I15 I 0.8168(3) 0.1043(5) 0.3968(2) 0.0539(9) Uani 0.35 d P 1 I16 I 0.9036(7) -0.1088(12) 0.5620(9) 0.089(4) Uani 0.15 d P 1 S1 S 0.4381(2) 0.3006(4) 0.5243(2) 0.0325(7) Uani 1 d . . S2 S 0.5228(4) 0.0897(5) 0.6585(2) 0.0493(10) Uani 1 d . . S3 S 0.6279(3) 0.1946(5) 0.4579(2) 0.0390(8) Uani 1 d . . S4 S 0.7013(3) -0.0117(5) 0.5958(2) 0.0505(10) Uani 1 d . . C1 C 0.5323(9) 0.1672(16) 0.5712(6) 0.030(3) Uani 1 d . . C2 C 0.3804(11) 0.2986(20) 0.5965(8) 0.043(3) Uani 1 d D . C3 C 0.4204(14) 0.2020(20) 0.6594(8) 0.050(4) Uani 1 d D . C4 C 0.6115(10) 0.1210(17) 0.5433(7) 0.035(3) Uani 1 d . . C5 C 0.7438(13) 0.0966(22) 0.4723(12) 0.061(5) Uani 1 d D . C6 C 0.7773(10) 0.0029(19) 0.5398(12) 0.057(5) Uani 1 d D . C12 C 0.2873(27) 0.4018(62) 0.5720(27) 0.132(21) Uiso 0.75 d PD 2 H121 H 0.2433(27) 0.3887(62) 0.5187(27) 0.198 Uiso 0.75 d PR 2 H122 H 0.3053(27) 0.5187(62) 0.5818(27) 0.198 Uiso 0.75 d PR 2 H123 H 0.2527(27) 0.3639(62) 0.6090(27) 0.198 Uiso 0.75 d PR 2 C13 C 0.3831(68) 0.2050(123) 0.7296(35) 0.245(50) Uiso 0.75 d PD 2 H131 H 0.4352(68) 0.2454(123) 0.7754(35) 0.367 Uiso 0.75 d PR 2 H132 H 0.3617(68) 0.0945(123) 0.7404(35) 0.367 Uiso 0.75 d PR 2 H133 H 0.3259(68) 0.2806(123) 0.7179(35) 0.367 Uiso 0.75 d PR 2 C15 C 0.7997(37) 0.1332(75) 0.4144(25) 0.105(22) Uiso 0.65 d PD 2 H151 H 0.7819(37) 0.2449(75) 0.3937(25) 0.157 Uiso 0.65 d PR 2 H152 H 0.7786(37) 0.0527(75) 0.3719(25) 0.157 Uiso 0.65 d PR 2 H153 H 0.8721(37) 0.1260(75) 0.4380(25) 0.157 Uiso 0.65 d PR 2 C16 C 0.8736(18) -0.0931(45) 0.5676(20) 0.084(11) Uiso 0.85 d PD 2 H161 H 0.8677(18) -0.1720(45) 0.6075(20) 0.126 Uiso 0.85 d PR 2 H162 H 0.9294(18) -0.0176(45) 0.5901(20) 0.126 Uiso 0.85 d PR 2 H163 H 0.8857(18) -0.1534(45) 0.5239(20) 0.126 Uiso 0.85 d PR 2 loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 I1 0.0549(6) 0.0419(6) 0.0515(6) -0.0063(5) -0.0130(5) 0.0094(5) I2 0.0807(7) 0.0306(5) 0.0206(4) -0.0014(3) -0.0051(4) -0.0026(5) I3 0.1048(10) 0.0522(7) 0.0494(6) -0.0116(5) 0.0392(6) -0.0154(7) I4 0.0557(7) 0.0997(11) 0.0549(6) 0.0056(7) 0.0296(5) 0.0077(7) I12 0.059(3) 0.042(2) 0.070(3) -0.015(2) 0.023(2) 0.004(2) I13 0.253(12) 0.049(3) 0.106(5) -0.011(3) 0.128(7) -0.021(5) I15 0.055(2) 0.061(2) 0.057(2) -0.003(2) 0.034(2) -0.011(2) I16 0.033(4) 0.036(4) 0.192(13) -0.022(6) 0.025(6) 0.005(4) S1 0.037(2) 0.028(2) 0.0284(13) 0.0000(12) 0.0031(12) -0.0019(14) S2 0.083(3) 0.035(2) 0.0243(14) 0.0019(14) 0.007(2) 0.001(2) S3 0.039(2) 0.037(2) 0.038(2) -0.0043(15) 0.0090(14) -0.003(2) S4 0.041(2) 0.036(2) 0.056(2) -0.002(2) -0.014(2) 0.003(2) C1 0.032(6) 0.028(6) 0.023(5) 0.006(5) -0.003(5) -0.006(5) C2 0.043(8) 0.045(9) 0.042(7) -0.014(7) 0.017(6) -0.002(7) C3 0.076(11) 0.039(8) 0.037(7) -0.013(6) 0.023(7) -0.008(8) C4 0.035(7) 0.027(6) 0.034(6) -0.004(5) -0.005(5) -0.003(6) C5 0.047(9) 0.040(9) 0.102(14) -0.040(10) 0.029(9) -0.019(8) C6 0.020(6) 0.028(8) 0.101(13) -0.010(9) -0.014(7) -0.002(6) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag I1 I2 2.829(2) . ? I2 I3 3.047(2) . ? I3 I4 3.377(2) . ? I4 I4 2.788(3) 3_655 ? I12 C2 1.88(2) . ? I13 C3 1.88(2) . ? I15 C5 1.93(2) . ? I16 C6 1.92(2) . ? S1 C2 1.719(14) . ? S1 C1 1.720(13) . ? S2 C3 1.70(2) . ? S2 C1 1.730(12) . ? S3 C4 1.724(14) . ? S3 C5 1.76(2) . ? S4 C6 1.67(2) . ? S4 C4 1.710(13) . ? C1 C4 1.40(2) . ? C2 C3 1.35(2) . ? C2 C12 1.502(10) . ? C3 C13 1.502(10) . ? C5 C6 1.39(3) . ? C5 C15 1.506(10) . ? C6 C16 1.509(10) . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag I1 I2 I3 178.92(5) . . ? I2 I3 I4 118.83(5) . . ? I4 I4 I3 169.04(7) 3_655 . ? C2 S1 C1 95.2(7) . . ? C3 S2 C1 96.1(7) . . ? C4 S3 C5 94.3(8) . . ? C6 S4 C4 97.0(7) . . ? C4 C1 S1 124.7(9) . . ? C4 C1 S2 120.7(10) . . ? S1 C1 S2 114.6(8) . . ? C3 C2 C12 132.5(23) . . ? C3 C2 S1 117.7(12) . . ? C12 C2 S1 109.7(21) . . ? C3 C2 I12 114.4(11) . . ? S1 C2 I12 127.5(9) . . ? C2 C3 C13 122.1(41) . . ? C2 C3 S2 116.2(12) . . ? C13 C3 S2 121.4(40) . . ? C2 C3 I13 123.1(13) . . ? S2 C3 I13 120.6(10) . . ? C1 C4 S4 120.3(10) . . ? C1 C4 S3 123.8(10) . . ? S4 C4 S3 115.8(8) . . ? C6 C5 C15 126.8(28) . . ? C6 C5 S3 115.7(13) . . ? C15 C5 S3 117.3(27) . . ? C6 C5 I15 121.2(14) . . ? S3 C5 I15 122.9(13) . . ? C5 C6 C16 127.5(22) . . ? C5 C6 S4 116.9(11) . . ? C16 C6 S4 115.6(18) . . ? C5 C6 I16 119.4(15) . . ? S4 C6 I16 123.7(12) . . ? _refine_diff_density_max 1.836 _refine_diff_density_min -2.108 _refine_diff_density_rms 0.298 #==================================END data_16.I3 _database_code_CSD 161762 _audit_creation_method SHELXL _chemical_name_systematic ; 4,5-dibromo-4',5'-bis(methylsulfanyl)tetrathiafulvalenium triiodide ; _chemical_name_common ? _chemical_formula_moiety 'C8 H6 Br2 S6 1+,I3 1-' _chemical_formula_sum 'C8 H6 Br2 I3 S6' _chemical_formula_weight 835.01 _chemical_melting_point ? _chemical_compound_source ? _ccdc_compound_id '16.I3' _ccdc_biological_activity '?' _ccdc_polymorph '?' _ccdc_disorder 'none' _ccdc_comments 'repeat of NIQCOF' loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source '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' 'S' 'S' 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 'Br' 'Br' -0.2901 2.4595 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 'I' 'I' -0.4742 1.8119 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting 'Orthorhombic' _symmetry_space_group_name_H-M 'Cmcm ' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, z+1/2' '-x, y, -z+1/2' 'x, -y, -z' 'x+1/2, y+1/2, z' '-x+1/2, -y+1/2, z+1/2' '-x+1/2, y+1/2, -z+1/2' 'x+1/2, -y+1/2, -z' '-x, -y, -z' 'x, y, -z-1/2' 'x, -y, z-1/2' '-x, y, z' '-x+1/2, -y+1/2, -z' 'x+1/2, y+1/2, -z-1/2' 'x+1/2, -y+1/2, z-1/2' '-x+1/2, y+1/2, z' _cell_length_a 7.098(1) _cell_length_b 16.255(1) _cell_length_c 16.541(1) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 1908.5(3) _cell_formula_units_Z 4 _cell_measurement_temperature 150(2) _cell_measurement_reflns_used 418 _cell_measurement_theta_min 12.0 _cell_measurement_theta_max 28.4 _exptl_crystal_description plate _exptl_crystal_colour black _exptl_crystal_size_max 0.3 _exptl_crystal_size_mid 0.3 _exptl_crystal_size_min 0.04 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 2.906 _exptl_crystal_density_method ? _exptl_crystal_F_000 1516 _exptl_absorpt_coefficient_mu 9.741 _exptl_absorpt_correction_type 'integration' _exptl_absorpt_correction_T_min 0.0928 _exptl_absorpt_correction_T_max 0.6776 _exptl_absorpt_process_details 'XPREP (SHELXTL,1997), R(int)=0.173 before correction' loop_ _exptl_crystal_face_index_h _exptl_crystal_face_index_k _exptl_crystal_face_index_l _exptl_crystal_face_perp_dist 0.00 0.00 -1.00 0.02 0.00 0.00 1.00 0.02 0.00 -1.00 0.00 0.15 0.00 1.00 0.00 0.15 1.00 0.00 0.00 0.15 -1.00 0.00 0.00 0.15 _exptl_special_details ; The data collection nominally covered over a hemisphere of reciprocal space, by a combination of 4 sets of \w scans; each set at different \f and/or 2\q angles and each scan (10 sec exposure) covering 0.3\% in \w. Crystal to detector distance 4.51 cm. Crystal decay was monitored by repeating 50 initial frames at the end of data collection and comparing 158 duplicate reflections. ; _diffrn_ambient_temperature 150(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device 'SMART 1K CCD area detector' _diffrn_measurement_method '\w scans' _diffrn_standards_number . _diffrn_standards_interval_count . _diffrn_standards_interval_time . _diffrn_standards_decay_% 0 _diffrn_reflns_number 9133 _diffrn_reflns_av_R_equivalents 0.0557 _diffrn_reflns_av_sigmaI/netI 0.0272 _diffrn_reflns_limit_h_min -9 _diffrn_reflns_limit_h_max 9 _diffrn_reflns_limit_k_min -22 _diffrn_reflns_limit_k_max 21 _diffrn_reflns_limit_l_min -23 _diffrn_reflns_limit_l_max 21 _diffrn_reflns_theta_min 2.46 _diffrn_reflns_theta_max 30.46 _reflns_number_total 1508 _reflns_number_observed 1345 _reflns_observed_criterion I>2\s(I) _computing_data_collection 'Siemens SMART' _computing_cell_refinement 'Siemens SMART' _computing_data_reduction 'Siemens SAINT' _computing_structure_solution 'SHELXS-86 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-93 (Sheldrick, 1993)' _computing_molecular_graphics 'Siemens SHELXTL' _computing_publication_material 'Siemens SHELXTL' _refine_special_details ; Refinement on F^2^ for ALL reflections except for 4 with very negative F^2^ or flagged by the user for potential systematic errors. Weighted R-factors wR and all goodnesses of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The observed criterion of F^2^ > 2sigma(F^2^) is used only for calculating _R_factor_obs etc. and is not relevant to the choice of reflections for refinement. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme 'calc w=1/[\s^2^(Fo^2^)+(0.0225P)^2^+4.8709P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens difmap _refine_ls_hydrogen_treatment refall _refine_ls_extinction_method SHELXL _refine_ls_extinction_coef 0.00064(7) _refine_ls_extinction_expression 'Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^' _refine_ls_number_reflns 1504 _refine_ls_number_parameters 69 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0305 _refine_ls_R_factor_obs 0.0245 _refine_ls_wR_factor_all 0.0614 _refine_ls_wR_factor_obs 0.0561 _refine_ls_goodness_of_fit_all 1.188 _refine_ls_goodness_of_fit_obs 1.178 _refine_ls_restrained_S_all 1.215 _refine_ls_restrained_S_obs 1.178 _refine_ls_shift/esd_max 0.001 _refine_ls_shift/esd_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_thermal_displace_type _atom_site_occupancy _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_group I1 I 0.5000 0.14916(2) 0.2500 0.01699(10) Uani 1 d S . I2 I 0.5000 0.14591(2) 0.42651(2) 0.02518(10) Uani 1 d S . Br Br 0.5000 0.93638(2) 0.35518(2) 0.01918(11) Uani 1 d S . S1 S 0.5000 0.74660(6) 0.33873(6) 0.0193(2) Uani 1 d S . S2 S 0.5000 0.54729(6) 0.33803(6) 0.0190(2) Uani 1 d S . S3 S 0.5000 0.35965(6) 0.34632(6) 0.0187(2) Uani 1 d S . C1 C 0.5000 0.6893(3) 0.2500 0.0188(11) Uani 1 d S . C2 C 0.5000 0.8417(2) 0.2902(2) 0.0163(7) Uani 1 d S . C3 C 0.5000 0.6048(3) 0.2500 0.0170(10) Uani 1 d S . C4 C 0.5000 0.4517(2) 0.2913(2) 0.0169(7) Uani 1 d S . C5 C 0.5000 0.3963(3) 0.4492(3) 0.0261(9) Uani 1 d S . H51 H 0.3798(50) 0.4276(22) 0.4592(21) 0.025(9) Uiso 1 d . . H52 H 0.5000 0.3513(38) 0.4809(48) 0.057(21) Uiso 1 d S . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 I1 0.0166(2) 0.0159(2) 0.0185(2) 0.000 0.000 0.000 I2 0.0343(2) 0.0243(2) 0.01695(15) 0.00063(9) 0.000 0.000 Br 0.0233(2) 0.0158(2) 0.0185(2) -0.00205(14) 0.000 0.000 S1 0.0259(5) 0.0143(4) 0.0177(5) 0.0004(3) 0.000 0.000 S2 0.0260(5) 0.0137(4) 0.0174(5) -0.0011(3) 0.000 0.000 S3 0.0251(5) 0.0143(4) 0.0166(5) 0.0005(3) 0.000 0.000 C1 0.018(2) 0.016(2) 0.022(3) 0.000 0.000 0.000 C2 0.020(2) 0.012(2) 0.017(2) 0.0001(13) 0.000 0.000 C3 0.014(2) 0.016(2) 0.021(3) 0.000 0.000 0.000 C4 0.019(2) 0.013(2) 0.019(2) -0.0012(14) 0.000 0.000 C5 0.043(3) 0.023(2) 0.013(2) -0.0003(15) 0.000 0.000 _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag I1 I2 2.9200(3) 10_556 ? I1 I2 2.9201(3) . ? I1 S3 3.7744(10) . ? I2 S3 3.7190(10) . ? Br C2 1.876(4) . ? Br I2 3.6044(5) 1_565 ? Br I2 3.8509(5) 9_666 ? Br I1 3.8717(5) 1_565 ? S2 C3 1.730(3) . ? S2 C4 1.736(4) . ? S1 C1 1.738(3) . ? S1 C2 1.742(4) . ? S3 C4 1.751(4) . ? S3 C5 1.803(4) . ? C1 C3 1.374(8) . ? C1 S1 1.738(3) 10_556 ? C2 C2 1.331(8) 10_556 ? C3 S2 1.730(3) 10_556 ? C4 C4 1.366(8) 10_556 ? C5 H51 1.01(4) . ? C5 H52 0.90(7) . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag I2 I1 I2 177.92(2) 10_556 . ? I2 I1 S3 116.01(2) 10_556 . ? I2 I1 S3 66.07(2) . . ? I1 I2 S3 68.07(2) . . ? C2 Br I2 164.19(12) . 1_565 ? C2 Br I2 104.60(12) . 9_666 ? I2 Br I2 91.218(11) 1_565 9_666 ? C2 Br I1 118.38(12) . 1_565 ? I2 Br I1 45.808(8) 1_565 1_565 ? I2 Br I1 137.026(12) 9_666 1_565 ? C3 S2 C4 96.3(2) . . ? C1 S1 C2 95.0(2) . . ? C4 S3 C5 102.0(2) . . ? C4 S3 I2 169.58(13) . . ? C5 S3 I2 88.38(15) . . ? C4 S3 I1 123.72(13) . . ? C5 S3 I1 134.2(2) . . ? I2 S3 I1 45.862(13) . . ? C3 C1 S1 122.4(2) . 10_556 ? C3 C1 S1 122.4(2) . . ? S1 C1 S1 115.2(3) 10_556 . ? C2 C2 S1 117.42(13) 10_556 . ? C2 C2 Br 124.92(12) 10_556 . ? S1 C2 Br 117.7(2) . . ? C1 C3 S2 122.7(2) . . ? C1 C3 S2 122.7(2) . 10_556 ? S2 C3 S2 114.6(3) . 10_556 ? C4 C4 S2 116.45(13) 10_556 . ? C4 C4 S3 121.31(13) 10_556 . ? S2 C4 S3 122.2(2) . . ? S3 C5 H51 108.7(21) . . ? S3 C5 H52 106.3(47) . . ? H51 C5 H52 108.4(28) . . ? _refine_diff_density_max 1.042 _refine_diff_density_min -0.880 _refine_diff_density_rms 0.154 #========================================END data_1.19 _database_code_CSD 161763 _audit_creation_method SHELXL _chemical_name_systematic ; 4-iodotetrathiafulvalene 2,4,5,7-tetranitro-9- dicyanomethylenefluorene bis-dioxane ; _chemical_name_common ? _chemical_formula_moiety 'C16 H4 N6 O8,C6 H3 S4 I,2(C4 H8 O2)' _chemical_formula_sum 'C30 H23 I N6 O12 S4' _chemical_formula_weight 914.68 _chemical_melting_point ? _chemical_compound_source ? _ccdc_compound_id '1.19' _ccdc_biological_activity '?' _ccdc_polymorph '?' _ccdc_disorder 'none' _ccdc_comments '?' loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source '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' 'N' 'N' 0.0061 0.0033 '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' 'S' 'S' 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 'I' 'I' -0.4742 1.8119 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting 'Monoclinic' _symmetry_space_group_name_H-M 'P2(1)/c ' 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' _cell_length_a 10.178(1) _cell_length_b 24.490(1) _cell_length_c 14.101(1) _cell_angle_alpha 90.00 _cell_angle_beta 100.99(1) _cell_angle_gamma 90.00 _cell_volume 3450.3(4) _cell_formula_units_Z 4 _cell_measurement_temperature 150(2) _cell_measurement_reflns_used 512 _cell_measurement_theta_min 4 _cell_measurement_theta_max 26 _exptl_crystal_description 'prism' _exptl_crystal_colour 'greenish black' _exptl_crystal_size_max 0.40 _exptl_crystal_size_mid 0.14 _exptl_crystal_size_min 0.07 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.761 _exptl_crystal_density_method ? _exptl_crystal_F_000 1832 _exptl_absorpt_coefficient_mu 1.243 _exptl_absorpt_correction_type 'integration' _exptl_absorpt_correction_T_min 0.6766 _exptl_absorpt_correction_T_max 0.9185 _exptl_absorpt_process_details 'XPREP (SHELXTL,1997), R(int)=0.047 before correction' loop_ _exptl_crystal_face_index_h _exptl_crystal_face_index_k _exptl_crystal_face_index_l _exptl_crystal_face_perp_dist 0.00 -1.00 0.00 0.0350 0.00 1.00 0.00 0.0350 -1.00 0.00 0.00 0.0700 1.00 0.00 0.00 0.0700 0.00 -1.00 -2.00 0.1800 0.00 0.00 1.00 0.1800 1.00 1.00 -2.00 0.1800 _exptl_special_details ; The data collection nominally covered over a hemisphere of reciprocal space, by a combination of 5 sets of \w scans; each set at different \f and/or 2\q angles and each scan (25 sec exposure) covering 0.3\% in \w. Crystal to detector distance 4.51 cm. Crystal decay was monitored by repeating 50 initial frames at the end of data collection and comparing 477 duplicate reflections. ; _diffrn_ambient_temperature 150(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device 'SMART 1K CCD area detector' _diffrn_measurement_method '\w scans' _diffrn_standards_number . _diffrn_standards_interval_count . _diffrn_standards_interval_time . _diffrn_standards_decay_% 0 _diffrn_reflns_number 27818 _diffrn_reflns_av_R_equivalents 0.0337 _diffrn_reflns_av_sigmaI/netI 0.0321 _diffrn_reflns_limit_h_min -14 _diffrn_reflns_limit_h_max 9 _diffrn_reflns_limit_k_min -33 _diffrn_reflns_limit_k_max 33 _diffrn_reflns_limit_l_min -19 _diffrn_reflns_limit_l_max 18 _diffrn_reflns_theta_min 1.66 _diffrn_reflns_theta_max 30.36 _reflns_number_total 9517 _reflns_number_observed 7789 _reflns_observed_criterion I>2\s(I) _computing_data_collection 'Siemens SMART' _computing_cell_refinement 'Siemens SMART' _computing_data_reduction 'Siemens SAINT' _computing_structure_solution 'SHELXS-86 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-93 (Sheldrick, 1993)' _computing_molecular_graphics 'SHELXTL' _computing_publication_material 'SHELXTL' _refine_special_details ; Refinement on F^2^ for ALL reflections except for 70 with very negative F^2^ or flagged by the user for potential systematic errors. Weighted R-factors wR and all goodnesses of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The observed criterion of F^2^ > 2sigma(F^2^) is used only for calculating _R_factor_obs etc. and is not relevant to the choice of reflections for refinement. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme 'calc w=1/[\s^2^(Fo^2^)+(0.0004P)^2^+5.2141P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens difmap _refine_ls_hydrogen_treatment refall _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 9447 _refine_ls_number_parameters 569 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0507 _refine_ls_R_factor_obs 0.0344 _refine_ls_wR_factor_all 0.0764 _refine_ls_wR_factor_obs 0.0630 _refine_ls_goodness_of_fit_all 1.190 _refine_ls_goodness_of_fit_obs 1.159 _refine_ls_restrained_S_all 1.264 _refine_ls_restrained_S_obs 1.159 _refine_ls_shift/esd_max -0.002 _refine_ls_shift/esd_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_thermal_displace_type _atom_site_occupancy _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_group I I 0.69842(2) 0.417503(7) 0.648373(14) 0.02904(5) Uani 1 d . . S1 S 0.50338(6) 0.31337(2) 0.57740(4) 0.01963(12) Uani 1 d . . S2 S 0.71164(6) 0.22800(3) 0.62116(5) 0.02202(12) Uani 1 d . . S3 S 0.27619(6) 0.21945(2) 0.52022(4) 0.02023(12) Uani 1 d . . S4 S 0.47928(6) 0.13359(2) 0.57870(4) 0.02115(12) Uani 1 d . . C1T C 0.5410(2) 0.24321(10) 0.5835(2) 0.0182(4) Uani 1 d . . C2T C 0.6672(2) 0.33423(10) 0.6258(2) 0.0208(5) Uani 1 d . . C3T C 0.7614(2) 0.29560(10) 0.6453(2) 0.0223(5) Uani 1 d . . H3T H 0.8483(31) 0.3040(12) 0.6655(21) 0.029(8) Uiso 1 d . . C4T C 0.4450(2) 0.20375(9) 0.5625(2) 0.0170(4) Uani 1 d . . C5T C 0.2213(3) 0.15177(11) 0.5152(2) 0.0257(5) Uani 1 d . . H5T H 0.1294(31) 0.1400(12) 0.4979(21) 0.031 Uiso 1 d . . C6T C 0.3133(3) 0.11294(11) 0.5416(2) 0.0257(5) Uani 1 d . . H6T H 0.2934(34) 0.0758(15) 0.5415(25) 0.047(10) Uiso 1 d . . N2 N 0.4826(2) 0.02526(8) 0.3640(2) 0.0225(4) Uani 1 d . . N4 N 0.1361(2) 0.15410(8) 0.22187(15) 0.0187(4) Uani 1 d . . N5 N 0.1029(2) 0.27306(8) 0.25311(15) 0.0192(4) Uani 1 d . . N7 N 0.4236(2) 0.42183(8) 0.30527(15) 0.0209(4) Uani 1 d . . N15 N 0.8775(2) 0.14995(10) 0.4157(2) 0.0308(5) Uani 1 d . . N16 N 0.8416(2) 0.32300(11) 0.4099(2) 0.0401(6) Uani 1 d . . O21 O 0.5895(2) 0.01790(8) 0.4195(2) 0.0388(5) Uani 1 d . . O22 O 0.4080(2) -0.01155(7) 0.3283(2) 0.0323(4) Uani 1 d . . O41 O 0.0454(2) 0.12805(7) 0.24605(14) 0.0277(4) Uani 1 d . . O42 O 0.1229(2) 0.18572(7) 0.15236(12) 0.0236(4) Uani 1 d . . O51 O 0.0666(2) 0.24165(7) 0.31139(13) 0.0238(4) Uani 1 d . . O52 O 0.0287(2) 0.29485(7) 0.18497(15) 0.0300(4) Uani 1 d . . O71 O 0.3452(2) 0.45121(7) 0.25115(14) 0.0266(4) Uani 1 d . . O72 O 0.5226(2) 0.43835(7) 0.36188(14) 0.0300(4) Uani 1 d . . C1 C 0.5383(2) 0.12282(9) 0.3603(2) 0.0175(4) Uani 1 d . . H1 H 0.6293(28) 0.1134(11) 0.3916(20) 0.022(7) Uiso 1 d . . C2 C 0.4417(2) 0.08208(9) 0.3393(2) 0.0177(4) Uani 1 d . . C3 C 0.3098(2) 0.09234(9) 0.2978(2) 0.0173(4) Uani 1 d . . H3 H 0.2442(28) 0.0638(11) 0.2841(19) 0.021(7) Uiso 1 d . . C4 C 0.2728(2) 0.14625(9) 0.2767(2) 0.0152(4) Uani 1 d . . C5 C 0.2459(2) 0.28833(9) 0.2710(2) 0.0146(4) Uani 1 d . . C6 C 0.2684(2) 0.34430(9) 0.2687(2) 0.0163(4) Uani 1 d . . H6 H 0.1997(28) 0.3669(12) 0.2464(20) 0.022(7) Uiso 1 d . . C7 C 0.3984(2) 0.36266(9) 0.3018(2) 0.0157(4) Uani 1 d . . C8 C 0.5051(2) 0.32813(9) 0.3338(2) 0.0163(4) Uani 1 d . . H8 H 0.5939(30) 0.3436(12) 0.3565(21) 0.028(8) Uiso 1 d . . C9 C 0.5767(2) 0.22718(9) 0.3554(2) 0.0157(4) Uani 1 d . . C10 C 0.4973(2) 0.17674(9) 0.3401(2) 0.0143(4) Uani 1 d . . C11 C 0.3610(2) 0.18998(9) 0.3010(2) 0.0138(4) Uani 1 d . . C12 C 0.3502(2) 0.25036(9) 0.2971(2) 0.0143(4) Uani 1 d . . C13 C 0.4813(2) 0.27208(9) 0.3288(2) 0.0149(4) Uani 1 d . . C14 C 0.7129(2) 0.23149(10) 0.3856(2) 0.0189(4) Uani 1 d . . C15 C 0.8019(2) 0.18522(10) 0.4029(2) 0.0214(5) Uani 1 d . . C16 C 0.7830(2) 0.28289(11) 0.3982(2) 0.0238(5) Uani 1 d . . O1A O 0.0100(2) 0.42438(8) 0.2308(2) 0.0403(5) Uani 1 d . . C2A C -0.1251(3) 0.41683(14) 0.1832(4) 0.0547(11) Uani 1 d . . H21A H -0.1390(38) 0.3782(17) 0.1742(28) 0.061(12) Uiso 1 d . . H22A H -0.1932(46) 0.4330(18) 0.2210(31) 0.078(14) Uiso 1 d . . C3A C -0.1511(5) 0.4448(2) 0.0895(3) 0.0580(11) Uani 1 d . . H31A H -0.2396(43) 0.4416(16) 0.0565(29) 0.063(12) Uiso 1 d . . H32A H -0.0940(31) 0.4437(13) 0.0477(22) 0.023(8) Uiso 1 d . . O4A O -0.1215(3) 0.50267(9) 0.0981(2) 0.0450(6) Uani 1 d . . C5A C 0.0145(3) 0.50940(14) 0.1472(3) 0.0424(8) Uani 1 d . . H51A H 0.0292(32) 0.5488(14) 0.1508(23) 0.040(9) Uiso 1 d . . H52A H 0.0733(39) 0.4938(16) 0.1092(28) 0.059(12) Uiso 1 d . . C6A C 0.0358(3) 0.48139(12) 0.2426(2) 0.0357(7) Uani 1 d . . H61A H -0.0181(32) 0.4968(13) 0.2842(22) 0.033(8) Uiso 1 d . . H62A H 0.1241(37) 0.4831(14) 0.2787(25) 0.048(10) Uiso 1 d . . O1B O 0.2579(2) 0.07725(8) -0.05814(13) 0.0302(4) Uani 1 d . . C2B C 0.1510(3) 0.11066(12) -0.0371(2) 0.0287(6) Uani 1 d . . H21B H 0.1876(32) 0.1393(14) 0.0014(23) 0.035(9) Uiso 1 d . . H22B H 0.1041(31) 0.1243(13) -0.0994(23) 0.032(8) Uiso 1 d . . C3B C 0.0578(3) 0.07744(12) 0.0108(2) 0.0251(5) Uani 1 d . . H31B H 0.0187(28) 0.0486(12) -0.0329(21) 0.024(7) Uiso 1 d . . H32B H -0.0086(28) 0.1020(12) 0.0291(20) 0.022(7) Uiso 1 d . . O4B O 0.1278(2) 0.05206(8) 0.09691(13) 0.0278(4) Uani 1 d . . C5B C 0.2335(3) 0.01849(11) 0.0753(2) 0.0279(6) Uani 1 d . . H51B H 0.1944(30) -0.0098(13) 0.0321(21) 0.028(8) Uiso 1 d . . H52B H 0.2826(33) 0.0029(14) 0.1376(25) 0.042(9) Uiso 1 d . . C6B C 0.3273(3) 0.05196(11) 0.0284(2) 0.0257(5) Uani 1 d . . H61B H 0.3703(30) 0.0808(13) 0.0750(21) 0.029(8) Uiso 1 d . . H62B H 0.3929(27) 0.0296(11) 0.0116(19) 0.019(7) Uiso 1 d . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 I 0.02580(9) 0.02129(8) 0.03671(10) 0.00205(7) -0.00244(7) -0.00576(7) S1 0.0163(3) 0.0175(3) 0.0234(3) -0.0017(2) -0.0003(2) 0.0021(2) S2 0.0166(3) 0.0233(3) 0.0247(3) -0.0006(2) 0.0001(2) 0.0048(2) S3 0.0170(3) 0.0195(3) 0.0236(3) -0.0002(2) 0.0024(2) 0.0018(2) S4 0.0256(3) 0.0175(3) 0.0206(3) 0.0015(2) 0.0050(2) 0.0049(2) C1T 0.0177(11) 0.0203(11) 0.0163(11) -0.0009(9) 0.0029(8) 0.0038(9) C2T 0.0192(11) 0.0218(11) 0.0204(12) -0.0003(9) 0.0010(9) -0.0040(9) C3T 0.0167(11) 0.0258(12) 0.0230(12) 0.0004(10) 0.0001(9) -0.0012(9) C4T 0.0177(11) 0.0182(10) 0.0150(10) -0.0005(8) 0.0033(8) 0.0031(8) C5T 0.0251(13) 0.0260(13) 0.0265(13) -0.0020(10) 0.0065(10) -0.0050(10) C6T 0.0322(14) 0.0199(12) 0.0257(13) -0.0002(10) 0.0078(11) -0.0046(10) N2 0.0275(11) 0.0140(9) 0.0255(11) -0.0009(8) 0.0042(9) 0.0041(8) N4 0.0160(9) 0.0146(9) 0.0243(10) -0.0041(8) 0.0013(8) -0.0003(7) N5 0.0139(9) 0.0146(9) 0.0280(11) -0.0038(8) 0.0009(8) 0.0014(7) N7 0.0221(10) 0.0162(9) 0.0257(10) -0.0003(8) 0.0081(8) -0.0031(8) N15 0.0207(11) 0.0320(12) 0.0402(14) 0.0075(10) 0.0066(10) 0.0034(9) N16 0.0229(12) 0.0328(13) 0.061(2) -0.0053(12) -0.0007(12) -0.0059(10) O21 0.0436(12) 0.0198(9) 0.0437(12) -0.0009(9) -0.0154(10) 0.0085(8) O22 0.0266(10) 0.0153(8) 0.0543(13) -0.0012(8) 0.0058(9) -0.0010(7) O41 0.0172(8) 0.0226(9) 0.0440(11) -0.0006(8) 0.0072(8) -0.0042(7) O42 0.0253(9) 0.0226(9) 0.0203(9) -0.0017(7) -0.0026(7) 0.0020(7) O51 0.0195(8) 0.0228(9) 0.0306(10) -0.0035(7) 0.0085(7) -0.0046(7) O52 0.0202(9) 0.0220(9) 0.0419(11) 0.0031(8) -0.0086(8) 0.0026(7) O71 0.0307(10) 0.0156(8) 0.0340(10) 0.0053(7) 0.0077(8) 0.0021(7) O72 0.0287(10) 0.0218(9) 0.0379(11) -0.0058(8) 0.0023(8) -0.0100(7) C1 0.0174(11) 0.0174(10) 0.0173(11) -0.0019(9) 0.0022(9) 0.0034(8) C2 0.0211(11) 0.0137(10) 0.0182(10) 0.0021(9) 0.0038(9) 0.0039(9) C3 0.0191(11) 0.0143(10) 0.0188(11) -0.0010(8) 0.0046(9) -0.0016(8) C4 0.0124(10) 0.0164(10) 0.0165(10) -0.0012(8) 0.0018(8) -0.0009(8) C5 0.0137(10) 0.0151(10) 0.0150(10) -0.0014(8) 0.0025(8) -0.0007(8) C6 0.0180(11) 0.0152(10) 0.0156(10) -0.0006(8) 0.0025(8) 0.0025(8) C7 0.0200(11) 0.0123(10) 0.0156(10) -0.0009(8) 0.0052(8) -0.0016(8) C8 0.0162(10) 0.0160(10) 0.0173(11) -0.0014(8) 0.0044(8) -0.0026(8) C9 0.0150(10) 0.0167(10) 0.0147(10) -0.0011(8) 0.0011(8) 0.0002(8) C10 0.0123(10) 0.0160(10) 0.0144(10) -0.0017(8) 0.0021(8) -0.0002(8) C11 0.0148(10) 0.0136(10) 0.0137(10) 0.0004(8) 0.0039(8) 0.0000(8) C12 0.0147(10) 0.0157(10) 0.0128(10) -0.0006(8) 0.0035(8) 0.0006(8) C13 0.0136(10) 0.0179(10) 0.0134(10) -0.0002(8) 0.0031(8) -0.0007(8) C14 0.0164(11) 0.0206(11) 0.0199(11) -0.0031(9) 0.0039(9) -0.0007(8) C15 0.0153(11) 0.0268(12) 0.0219(12) -0.0002(10) 0.0033(9) -0.0019(9) C16 0.0139(11) 0.0261(12) 0.0297(13) -0.0019(10) -0.0005(9) -0.0001(9) O1A 0.0259(10) 0.0238(10) 0.0644(15) -0.0016(10) -0.0090(10) 0.0056(8) C2A 0.026(2) 0.0242(15) 0.103(3) 0.009(2) -0.015(2) 0.0012(13) C3A 0.054(2) 0.045(2) 0.064(3) -0.025(2) -0.017(2) 0.012(2) O4A 0.061(2) 0.0323(11) 0.0378(12) -0.0016(9) -0.0010(11) 0.0134(10) C5A 0.041(2) 0.030(2) 0.061(2) -0.005(2) 0.023(2) 0.0001(13) C6A 0.0269(14) 0.0308(15) 0.046(2) -0.0148(13) -0.0022(13) 0.0076(11) O1B 0.0282(10) 0.0379(11) 0.0275(10) 0.0100(8) 0.0130(8) 0.0092(8) C2B 0.0274(14) 0.0303(14) 0.0299(14) 0.0098(12) 0.0097(11) 0.0081(11) C3B 0.0189(11) 0.0307(13) 0.0256(12) 0.0016(11) 0.0040(10) 0.0027(10) O4B 0.0287(10) 0.0301(10) 0.0281(10) 0.0092(8) 0.0139(8) 0.0081(8) C5B 0.0280(14) 0.0241(13) 0.0338(15) 0.0062(12) 0.0116(11) 0.0079(10) C6B 0.0182(12) 0.0273(13) 0.0315(14) 0.0022(11) 0.0044(10) 0.0026(10) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag I C2T 2.079(2) . ? S1 C2T 1.753(2) . ? S1 C1T 1.759(2) . ? S2 C3T 1.746(3) . ? S2 C1T 1.757(2) . ? S3 C5T 1.746(3) . ? S3 C4T 1.750(2) . ? S4 C6T 1.746(3) . ? S4 C4T 1.760(2) . ? C1T C4T 1.366(3) . ? C2T C3T 1.338(3) . ? C3T H3T 0.90(3) . ? C5T C6T 1.336(4) . ? C5T H5T 0.96(3) . ? C6T H6T 0.93(4) . ? N2 O22 1.223(3) . ? N2 O21 1.226(3) . ? N2 C2 1.475(3) . ? N4 O41 1.223(3) . ? N4 O42 1.236(3) . ? N4 C4 1.470(3) . ? N5 O52 1.225(3) . ? N5 O51 1.233(3) . ? N5 C5 1.478(3) . ? N7 O71 1.226(3) . ? N7 O72 1.229(3) . ? N7 C7 1.471(3) . ? N15 C15 1.148(3) . ? N16 C16 1.145(3) . ? C1 C2 1.393(3) . ? C1 C10 1.398(3) . ? C1 H1 0.97(3) . ? C2 C3 1.381(3) . ? C3 C4 1.389(3) . ? C3 H3 0.96(3) . ? C4 C11 1.397(3) . ? C5 C6 1.391(3) . ? C5 C12 1.406(3) . ? C6 C7 1.390(3) . ? C6 H6 0.90(3) . ? C7 C8 1.383(3) . ? C8 C13 1.393(3) . ? C8 H8 0.98(3) . ? C9 C14 1.374(3) . ? C9 C13 1.468(3) . ? C9 C10 1.470(3) . ? C10 C11 1.429(3) . ? C11 C12 1.483(3) . ? C12 C13 1.427(3) . ? C14 C16 1.441(3) . ? C14 C15 1.443(3) . ? O1A C2A 1.422(4) . ? O1A C6A 1.425(3) . ? C2A C3A 1.467(6) . ? C2A H21A 0.96(4) . ? C2A H22A 1.03(4) . ? C3A O4A 1.449(5) . ? C3A H31A 0.93(4) . ? C3A H32A 0.90(3) . ? O4A C5A 1.434(4) . ? C5A C6A 1.488(5) . ? C5A H51A 0.98(3) . ? C5A H52A 0.96(4) . ? C6A H61A 0.95(3) . ? C6A H62A 0.95(4) . ? O1B C6B 1.429(3) . ? O1B C2B 1.437(3) . ? C2B C3B 1.505(4) . ? C2B H21B 0.92(3) . ? C2B H22B 0.97(3) . ? C3B O4B 1.427(3) . ? C3B H31B 0.97(3) . ? C3B H32B 0.97(3) . ? O4B C5B 1.432(3) . ? C5B C6B 1.505(4) . ? C5B H51B 0.96(3) . ? C5B H52B 1.00(3) . ? C6B H61B 1.01(3) . ? C6B H62B 0.93(3) . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C2T S1 C1T 94.81(11) . . ? C3T S2 C1T 95.24(12) . . ? C5T S3 C4T 95.22(12) . . ? C6T S4 C4T 95.00(12) . . ? C4T C1T S2 122.7(2) . . ? C4T C1T S1 122.7(2) . . ? S2 C1T S1 114.53(13) . . ? C3T C2T S1 117.7(2) . . ? C3T C2T I 125.4(2) . . ? S1 C2T I 116.86(13) . . ? C2T C3T S2 117.4(2) . . ? C2T C3T H3T 121.7(19) . . ? S2 C3T H3T 120.7(19) . . ? C1T C4T S3 122.2(2) . . ? C1T C4T S4 123.1(2) . . ? S3 C4T S4 114.60(13) . . ? C6T C5T S3 117.5(2) . . ? C6T C5T H5T 116.8(18) . . ? S3 C5T H5T 125.6(18) . . ? C5T C6T S4 117.6(2) . . ? C5T C6T H6T 123.6(22) . . ? S4 C6T H6T 118.7(22) . . ? O22 N2 O21 124.0(2) . . ? O22 N2 C2 118.2(2) . . ? O21 N2 C2 117.7(2) . . ? O41 N4 O42 125.0(2) . . ? O41 N4 C4 118.3(2) . . ? O42 N4 C4 116.6(2) . . ? O52 N5 O51 125.2(2) . . ? O52 N5 C5 117.6(2) . . ? O51 N5 C5 117.0(2) . . ? O71 N7 O72 124.5(2) . . ? O71 N7 C7 117.9(2) . . ? O72 N7 C7 117.6(2) . . ? C2 C1 C10 117.5(2) . . ? C2 C1 H1 119.9(17) . . ? C10 C1 H1 122.5(17) . . ? C3 C2 C1 123.4(2) . . ? C3 C2 N2 118.6(2) . . ? C1 C2 N2 118.0(2) . . ? C2 C3 C4 117.7(2) . . ? C2 C3 H3 122.4(17) . . ? C4 C3 H3 119.9(17) . . ? C3 C4 C11 122.7(2) . . ? C3 C4 N4 115.3(2) . . ? C11 C4 N4 121.9(2) . . ? C6 C5 C12 122.6(2) . . ? C6 C5 N5 114.0(2) . . ? C12 C5 N5 123.2(2) . . ? C7 C6 C5 117.5(2) . . ? C7 C6 H6 123.0(18) . . ? C5 C6 H6 119.5(18) . . ? C8 C7 C6 123.3(2) . . ? C8 C7 N7 118.0(2) . . ? C6 C7 N7 118.6(2) . . ? C7 C8 C13 117.9(2) . . ? C7 C8 H8 119.4(18) . . ? C13 C8 H8 122.7(18) . . ? C14 C9 C13 126.9(2) . . ? C14 C9 C10 127.2(2) . . ? C13 C9 C10 105.9(2) . . ? C1 C10 C11 121.6(2) . . ? C1 C10 C9 129.0(2) . . ? C11 C10 C9 109.4(2) . . ? C4 C11 C10 116.9(2) . . ? C4 C11 C12 135.7(2) . . ? C10 C11 C12 107.5(2) . . ? C5 C12 C13 116.7(2) . . ? C5 C12 C11 135.7(2) . . ? C13 C12 C11 107.6(2) . . ? C8 C13 C12 121.8(2) . . ? C8 C13 C9 128.7(2) . . ? C12 C13 C9 109.5(2) . . ? C9 C14 C16 123.5(2) . . ? C9 C14 C15 123.8(2) . . ? C16 C14 C15 112.6(2) . . ? N15 C15 C14 176.8(3) . . ? N16 C16 C14 178.1(3) . . ? C2A O1A C6A 108.8(2) . . ? O1A C2A C3A 110.9(3) . . ? O1A C2A H21A 107.2(23) . . ? C3A C2A H21A 110.1(24) . . ? O1A C2A H22A 113.0(25) . . ? C3A C2A H22A 105.3(25) . . ? H21A C2A H22A 110.4(34) . . ? O4A C3A C2A 112.5(3) . . ? O4A C3A H31A 106.9(25) . . ? C2A C3A H31A 113.5(26) . . ? O4A C3A H32A 86.3(21) . . ? C2A C3A H32A 123.0(20) . . ? H31A C3A H32A 110.6(32) . . ? C5A O4A C3A 108.6(3) . . ? O4A C5A C6A 110.2(3) . . ? O4A C5A H51A 105.3(20) . . ? C6A C5A H51A 114.5(20) . . ? O4A C5A H52A 109.4(24) . . ? C6A C5A H52A 108.9(24) . . ? H51A C5A H52A 108.4(30) . . ? O1A C6A C5A 110.8(3) . . ? O1A C6A H61A 110.2(19) . . ? C5A C6A H61A 111.8(19) . . ? O1A C6A H62A 104.0(22) . . ? C5A C6A H62A 115.2(21) . . ? H61A C6A H62A 104.4(27) . . ? C6B O1B C2B 110.0(2) . . ? O1B C2B C3B 110.6(2) . . ? O1B C2B H21B 108.5(20) . . ? C3B C2B H21B 111.5(20) . . ? O1B C2B H22B 105.6(18) . . ? C3B C2B H22B 110.4(18) . . ? H21B C2B H22B 110.1(27) . . ? O4B C3B C2B 111.3(2) . . ? O4B C3B H31B 107.5(17) . . ? C2B C3B H31B 109.0(17) . . ? O4B C3B H32B 107.7(16) . . ? C2B C3B H32B 108.2(16) . . ? H31B C3B H32B 113.3(24) . . ? C3B O4B C5B 110.0(2) . . ? O4B C5B C6B 110.3(2) . . ? O4B C5B H51B 108.2(18) . . ? C6B C5B H51B 109.5(18) . . ? O4B C5B H52B 107.6(19) . . ? C6B C5B H52B 110.0(19) . . ? H51B C5B H52B 111.2(26) . . ? O1B C6B C5B 111.1(2) . . ? O1B C6B H61B 109.6(17) . . ? C5B C6B H61B 109.2(17) . . ? O1B C6B H62B 107.5(17) . . ? C5B C6B H62B 109.8(17) . . ? H61B C6B H62B 109.7(24) . . ? _refine_diff_density_max 0.551 _refine_diff_density_min -0.697 _refine_diff_density_rms 0.085 #========================================END data_1.18 _database_code_CSD 161764 _audit_creation_method SHELXL-97 _chemical_name_systematic ; 2,4,7-trinitro-9-dicyanomethylenefluorene 4-iodotetrathiafulvalene ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C16 H5 N5 O6,C6 H3 S4 I' _chemical_formula_sum 'C22 H8 I N5 O6 S4' _chemical_formula_weight 693.47 _ccdc_compound_id '1.18' _ccdc_biological_activity '?' _ccdc_polymorph '?' _ccdc_disorder ; One nitro-group in 18 is disordered between positions 4 [N(4), O(3A), O(4A)] and 5 [N(5), O(3B), O(4B)] with occupancies 74(2)% and 26(2)%. The collateral disorder of 1 was not resolved, hence large residual electron density. ; _ccdc_comments '?' loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source 'C' 'C' 0.0181 0.0091 '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' 'N' 'N' 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 'O' 'O' 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 'S' 'S' 0.3331 0.5567 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 'I' 'I' -0.3257 6.8362 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Monoclinic _symmetry_space_group_name_H-M P2(1)/c 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' _cell_length_a 11.209(4) _cell_length_b 7.160(3) _cell_length_c 29.917(3) _cell_angle_alpha 90.00 _cell_angle_beta 94.03(2) _cell_angle_gamma 90.00 _cell_volume 2394.9(13) _cell_formula_units_Z 4 _cell_measurement_temperature 150(2) _cell_measurement_reflns_used 25 _cell_measurement_theta_min 13.2 _cell_measurement_theta_max 20.0 _exptl_crystal_description plate _exptl_crystal_colour purple _exptl_crystal_size_max 0.30 _exptl_crystal_size_mid 0.25 _exptl_crystal_size_min 0.01 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.923 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1360 _exptl_absorpt_coefficient_mu 14.238 _exptl_absorpt_correction_type ? _exptl_absorpt_correction_T_min 0.3816 _exptl_absorpt_correction_T_max 1.0000 _exptl_absorpt_process_details 'TEXSAN (MSC,1989), on \y-scans of 3 reflections' _exptl_special_details ; At room temperature, a=11.235(2), b=7.292(3), c=30.042(5), \b=93.90(2), V=2455(1). ; _diffrn_ambient_temperature 150(2) _diffrn_radiation_wavelength 1.54178 _diffrn_radiation_type CuK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Rigaku AFC6S 4-circle diffractometer' _diffrn_measurement_method '\w scans' _diffrn_standards_number 3 _diffrn_standards_interval_count 150 _diffrn_standards_interval_time . _diffrn_standards_decay_% 0 _diffrn_reflns_number 4070 _diffrn_reflns_av_R_equivalents 0.1084 _diffrn_reflns_av_sigmaI/netI 0.0991 _diffrn_reflns_limit_h_min -1 _diffrn_reflns_limit_h_max 11 _diffrn_reflns_limit_k_min -1 _diffrn_reflns_limit_k_max 8 _diffrn_reflns_limit_l_min -33 _diffrn_reflns_limit_l_max 33 _diffrn_reflns_theta_min 3.95 _diffrn_reflns_theta_max 59.99 _reflns_number_total 2913 _reflns_number_gt 2120 _reflns_threshold_expression I>2\s(I) _computing_data_collection 'AFC (MSC, 1989)' _computing_cell_refinement 'AFC (MSC, 1989)' _computing_data_reduction 'TEXSAN (MSC, 1989)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics SHELXTL _computing_publication_material SHELXTL _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.2000P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment constr _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 2913 _refine_ls_number_parameters 191 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.1581 _refine_ls_R_factor_gt 0.1299 _refine_ls_wR_factor_ref 0.3381 _refine_ls_wR_factor_gt 0.3127 _refine_ls_goodness_of_fit_ref 1.285 _refine_ls_restrained_S_all 1.285 _refine_ls_shift/su_max 0.007 _refine_ls_shift/su_mean 0.001 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group I I 0.61502(11) 0.1559(2) 0.56229(4) 0.0411(6) Uani 1 1 d . . . S1 S 0.3347(4) 0.0426(8) 0.56202(14) 0.0373(13) Uani 1 1 d . . . S2 S 0.3220(5) 0.0359(8) 0.66103(15) 0.0391(13) Uani 1 1 d . . . S3 S 0.0601(5) -0.0820(9) 0.54852(16) 0.0456(15) Uani 1 1 d . . . S4 S 0.0357(4) -0.0659(7) 0.64629(14) 0.0373(13) Uani 1 1 d . . . C1 C 0.5698(17) 0.432(3) 0.3664(6) 0.034(4) Uiso 1 1 d . A . H1 H 0.5103 0.4264 0.3422 0.041 Uiso 1 1 d R . . C2 C 0.5394(16) 0.401(3) 0.4092(6) 0.028(4) Uiso 1 1 d . . . C3 C 0.6212(17) 0.426(3) 0.4459(6) 0.035(5) Uiso 1 1 d . A . H3 H 0.5976 0.4113 0.4756 0.042 Uiso 1 1 d R . . C4 C 0.7381(15) 0.475(2) 0.4382(5) 0.024(4) Uiso 1 1 d . . . C5 C 1.0049(18) 0.563(3) 0.3966(6) 0.038(5) Uiso 1 1 d . . . C6 C 1.0998(18) 0.596(3) 0.3702(6) 0.033(4) Uiso 1 1 d . A . H6 H 1.1782 0.6155 0.3835 0.040 Uiso 1 1 d R . . C7 C 1.0782(18) 0.598(3) 0.3235(6) 0.038(5) Uiso 1 1 d . . . C8 C 0.9626(18) 0.576(3) 0.3037(7) 0.038(5) Uiso 1 1 d . A . H8 H 0.9492 0.5764 0.2720 0.046 Uiso 1 1 d R . . C9 C 0.7422(16) 0.503(3) 0.3177(6) 0.030(4) Uiso 1 1 d . A . C10 C 0.6876(17) 0.473(3) 0.3583(6) 0.032(4) Uiso 1 1 d . . . C11 C 0.7731(16) 0.496(3) 0.3958(6) 0.030(4) Uiso 1 1 d . A . C12 C 0.8896(17) 0.536(3) 0.3769(6) 0.033(4) Uiso 1 1 d . A . C13 C 0.8711(17) 0.553(3) 0.3294(6) 0.032(4) Uiso 1 1 d . . . C14 C 0.6926(17) 0.498(3) 0.2748(6) 0.036(5) Uiso 1 1 d . . . C15 C 0.5727(19) 0.429(3) 0.2638(7) 0.038(5) Uiso 1 1 d . A . C16 C 0.7464(19) 0.552(3) 0.2364(7) 0.042(5) Uiso 1 1 d . A . N2 N 0.4186(14) 0.351(2) 0.4175(5) 0.033(4) Uiso 1 1 d . . . N4 N 0.8135(17) 0.495(3) 0.4795(6) 0.027(5) Uiso 0.74(2) 1 d P A 1 N7 N 1.1774(16) 0.632(2) 0.2975(6) 0.044(4) Uiso 1 1 d . A . N15 N 0.4794(17) 0.371(3) 0.2552(6) 0.052(5) Uiso 1 1 d . . . N16 N 0.7955(18) 0.611(3) 0.2060(7) 0.060(5) Uiso 1 1 d . . . O1 O 0.3449(13) 0.328(2) 0.3855(5) 0.051(4) Uiso 1 1 d . . . O2 O 0.3885(13) 0.3353(19) 0.4574(5) 0.045(4) Uiso 1 1 d . . . O3A O 0.8017(16) 0.394(3) 0.5115(6) 0.037(5) Uiso 0.74(2) 1 d P A 1 O4A O 0.8855(19) 0.625(3) 0.4801(6) 0.040(5) Uiso 0.74(2) 1 d P A 1 O5 O 1.2761(15) 0.657(2) 0.3146(6) 0.061(4) Uiso 1 1 d . . . O6 O 1.1569(15) 0.630(2) 0.2556(6) 0.062(4) Uiso 1 1 d . . . N5 N 1.033(6) 0.591(10) 0.442(2) 0.045(19) Uiso 0.26(2) 1 d P A 2 O3B O 0.953(4) 0.658(6) 0.4641(15) 0.026(12) Uiso 0.26(2) 1 d P A 2 O4B O 1.139(6) 0.575(9) 0.455(2) 0.058(18) Uiso 0.26(2) 1 d P A 2 C21 C 0.2466(16) 0.007(3) 0.6082(6) 0.027(4) Uiso 1 1 d . . . C22 C 0.4604(18) 0.090(3) 0.5959(6) 0.037(5) Uiso 1 1 d . . . C23 C 0.4562(18) 0.081(3) 0.6405(6) 0.035(5) Uiso 1 1 d . . . H23 H 0.5258 0.1007 0.6600 0.042 Uiso 1 1 d R . . C24 C 0.1319(17) -0.042(3) 0.6022(6) 0.034(5) Uiso 1 1 d . . . C25 C -0.0841(19) -0.110(3) 0.5687(7) 0.041(5) Uiso 1 1 d . . . H25 H -0.1524 -0.1240 0.5483 0.049 Uiso 1 1 d R . . C26 C -0.094(2) -0.109(3) 0.6092(7) 0.047(6) Uiso 1 1 d . . . H26 H -0.1697 -0.1323 0.6208 0.056 Uiso 1 1 d R . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 I 0.0370(10) 0.0501(9) 0.0368(8) 0.0006(6) 0.0057(6) -0.0012(7) S1 0.038(3) 0.051(3) 0.022(2) -0.004(2) 0.001(2) -0.002(2) S2 0.039(3) 0.052(3) 0.026(2) -0.001(2) -0.002(2) 0.000(2) S3 0.035(3) 0.076(4) 0.024(2) -0.003(3) -0.004(2) -0.002(3) S4 0.039(3) 0.048(3) 0.025(2) -0.002(2) 0.002(2) -0.005(2) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag I C22 2.12(2) . ? S1 C22 1.71(2) . ? S1 C21 1.772(18) . ? S2 C23 1.69(2) . ? S2 C21 1.752(17) . ? S3 C24 1.767(19) . ? S3 C25 1.78(2) . ? S4 C24 1.771(19) . ? S4 C26 1.79(2) . ? C1 C2 1.37(3) . ? C1 C10 1.39(3) . ? C2 C3 1.39(3) . ? C2 N2 1.44(3) . ? C3 C4 1.39(3) . ? C4 C11 1.36(2) . ? C4 N4 1.46(3) . ? C5 N5 1.39(7) . ? C5 C6 1.39(3) . ? C5 C12 1.40(3) . ? C6 C7 1.40(3) . ? C7 C8 1.39(3) . ? C7 N7 1.42(3) . ? C8 C13 1.33(3) . ? C9 C14 1.36(3) . ? C9 C10 1.41(3) . ? C9 C13 1.50(3) . ? C10 C11 1.43(3) . ? C11 C12 1.49(3) . ? C12 C13 1.43(3) . ? C14 C16 1.39(3) . ? C14 C15 1.45(3) . ? C15 N15 1.14(2) . ? C16 N16 1.17(3) . ? N2 O1 1.23(2) . ? N2 O2 1.27(2) . ? N4 O3A 1.21(2) . ? N4 O4A 1.23(3) . ? N7 O5 1.20(2) . ? N7 O6 1.26(2) . ? N5 O4B 1.23(8) . ? N5 O3B 1.25(8) . ? C21 C24 1.33(3) . ? C22 C23 1.34(3) . ? C25 C26 1.23(3) . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C22 S1 C21 92.8(9) . . ? C23 S2 C21 94.6(9) . . ? C24 S3 C25 94.4(9) . . ? C24 S4 C26 93.8(10) . . ? C2 C1 C10 119.9(17) . . ? C1 C2 C3 121.7(18) . . ? C1 C2 N2 120.1(16) . . ? C3 C2 N2 118.1(16) . . ? C2 C3 C4 118.4(17) . . ? C11 C4 C3 121.3(16) . . ? C11 C4 N4 126.4(17) . . ? C3 C4 N4 112.3(16) . . ? N5 C5 C6 114(3) . . ? N5 C5 C12 125(3) . . ? C6 C5 C12 120.4(18) . . ? C5 C6 C7 119.0(19) . . ? C8 C7 C6 120.8(19) . . ? C8 C7 N7 121.7(18) . . ? C6 C7 N7 117.4(18) . . ? C13 C8 C7 120.0(19) . . ? C14 C9 C10 129.2(18) . . ? C14 C9 C13 123.0(17) . . ? C10 C9 C13 107.7(15) . . ? C1 C10 C9 130.9(17) . . ? C1 C10 C11 118.8(17) . . ? C9 C10 C11 110.3(16) . . ? C4 C11 C10 119.7(17) . . ? C4 C11 C12 133.9(17) . . ? C10 C11 C12 106.5(15) . . ? C5 C12 C13 118.4(17) . . ? C5 C12 C11 132.7(17) . . ? C13 C12 C11 108.9(16) . . ? C8 C13 C12 121.3(18) . . ? C8 C13 C9 131.4(17) . . ? C12 C13 C9 106.3(15) . . ? C9 C14 C16 126.8(19) . . ? C9 C14 C15 122.2(18) . . ? C16 C14 C15 111.0(17) . . ? N15 C15 C14 178(2) . . ? N16 C16 C14 174(2) . . ? O1 N2 O2 120.7(17) . . ? O1 N2 C2 119.2(16) . . ? O2 N2 C2 120.1(15) . . ? O3A N4 O4A 123(2) . . ? O3A N4 C4 121.6(19) . . ? O4A N4 C4 115.1(18) . . ? O5 N7 O6 121.7(19) . . ? O5 N7 C7 121.7(18) . . ? O6 N7 C7 116.7(18) . . ? O4B N5 O3B 126(6) . . ? O4B N5 C5 116(6) . . ? O3B N5 C5 117(5) . . ? C24 C21 S2 123.6(14) . . ? C24 C21 S1 121.2(14) . . ? S2 C21 S1 115.2(10) . . ? C23 C22 S1 119.7(16) . . ? C23 C22 I 124.8(15) . . ? S1 C22 I 115.5(10) . . ? C22 C23 S2 117.6(16) . . ? C21 C24 S3 122.6(14) . . ? C21 C24 S4 123.8(14) . . ? S3 C24 S4 113.5(11) . . ? C26 C25 S3 119.1(19) . . ? C25 C26 S4 119(2) . . ? _diffrn_measured_fraction_theta_max 0.821 _diffrn_reflns_theta_full 59.99 _diffrn_measured_fraction_theta_full 0.821 _refine_diff_density_max 5.204 _refine_diff_density_min -2.489 _refine_diff_density_rms 0.339 #===============================================END