# Copyright The Royal Society of Chemistry, 1999 # CCDC Number: 188/158 data_global _publ_contact_author 'Andrei S.Batsanov' _publ_contact_author_email a.s.batsanov@durham.ac.uk loop_ _publ_author_name 'Bryce, Martin R.' 'Lay, Alexander K.' 'Chesney, Anthony' 'Batsanov, Andrei S.' 'Howard, Judith A. K.' 'Buser, Urs' 'Gerson, Fabian' 'Merstetter, Pascal' _journal_name_full 'Journal of the Chemical Society, Perkin Transaction 2' _journal_volume '?' _journal_page_first '?' _journal_page_last '?' _journal_year '1999' _ccdc_journal_depnumber '188/??' _publ_section_title ; The radical ions of acenaphthyleno[1,2-b][1,4]dithiine derivatives and acenaphthyleno[1,2-b][1,4]oxathiine: solution EPR and ENDOR studies. The X-ray crystal structures of 8,9- di(methylsulfanyl)acenaphthyleno[1,2- b][1,4]dithiine 5 and its complexes with 7,7,8,8-tetracyano-p- quinodimethane (TCNQ), 2,5-dibromo-TCNQ and iodine. ; #====================================================================== data_(5) _audit_creation_method SHELXL _chemical_name_systematic ; 8,9-di(methylsulfanyl)acenaphthyleno[1,2-b][1,4]dithiine ; _chemical_name_common ? _chemical_formula_moiety ? _chemical_formula_structural ? _chemical_formula_analytical ? _chemical_formula_sum 'C16 H12 S4' _chemical_formula_weight 332.50 _chemical_melting_point '375-377 K' _chemical_compound_source ? _ccdc_compound_id '5' _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 '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 11.928(1) _cell_length_b 8.302(1) _cell_length_c 15.736(1) _cell_angle_alpha 90.00 _cell_angle_beta 103.34(1) _cell_angle_gamma 90.00 _cell_volume 1516.2(2) _cell_formula_units_Z 4 _cell_measurement_temperature 295(2) _cell_measurement_reflns_used 398 _cell_measurement_theta_min 10 _cell_measurement_theta_max 20 _exptl_crystal_description 'plate ' _exptl_crystal_colour 'purple ' _exptl_crystal_size_max 0.40 _exptl_crystal_size_mid 0.18 _exptl_crystal_size_min 0.08 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.457 _exptl_crystal_density_method ? _exptl_crystal_F_000 688 _exptl_absorpt_coefficient_mu 0.612 _exptl_absorpt_correction_type 'integration' _exptl_absorpt_correction_T_min 0.8319 _exptl_absorpt_correction_T_max 0.9576 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 0.0400 1.00 0.00 1.00 0.0400 0.00 0.00 -1.00 0.0900 0.00 0.00 1.00 0.0900 1.00 -3.00 1.00 0.2000 0.00 1.00 0.00 0.2000 _exptl_special_details ; Before absorption correction, R(int)=0.0425. ; _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 'Siemens CCD area detector' _diffrn_measurement_method '\w scan in 0.3\% frames, 10 s/frame' _diffrn_standards_number '128 (50 frames)' _diffrn_standards_interval_count ? _diffrn_standards_interval_time '8 h' _diffrn_standards_decay_% 0 _diffrn_reflns_number 9795 _diffrn_reflns_av_R_equivalents 0.0361 _diffrn_reflns_av_sigmaI/netI 0.0376 _diffrn_reflns_limit_h_min -15 _diffrn_reflns_limit_h_max 16 _diffrn_reflns_limit_k_min -10 _diffrn_reflns_limit_k_max 11 _diffrn_reflns_limit_l_min -22 _diffrn_reflns_limit_l_max 15 _diffrn_reflns_theta_min 1.94 _diffrn_reflns_theta_max 27.49 _reflns_number_total 3472 _reflns_number_observed 2533 _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 'SHELXTL, Version 5/VMS' _computing_publication_material 'SHELXTL, Version 5/VMS' _refine_special_details ; Refinement on F^2^ for ALL reflections except for 90 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. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme 'calc w=1/[\s^2^(Fo^2^)+(0.0143P)^2^+1.5947P] 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 0.0025(5) _refine_ls_extinction_expression 'Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^' _refine_ls_number_reflns 3382 _refine_ls_number_parameters 230 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0763 _refine_ls_R_factor_obs 0.0466 _refine_ls_wR_factor_all 0.1048 _refine_ls_wR_factor_obs 0.0829 _refine_ls_goodness_of_fit_all 1.106 _refine_ls_goodness_of_fit_obs 1.134 _refine_ls_restrained_S_all 1.210 _refine_ls_restrained_S_obs 1.134 _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 S1 S 0.29073(6) 0.54232(9) 0.21419(4) 0.0452(2) Uani 1 d . . S2 S 0.38873(7) 0.87233(9) 0.14030(5) 0.0461(2) Uani 1 d . . S3 S 0.48529(8) 0.56965(10) 0.37575(5) 0.0610(3) Uani 1 d . . S4 S 0.56838(7) 0.90238(11) 0.30066(5) 0.0556(2) Uani 1 d . . C1 C 0.3058(2) 0.4315(3) 0.0430(2) 0.0405(6) Uani 1 d . . C2 C 0.2739(3) 0.2721(4) 0.0375(2) 0.0491(7) Uani 1 d . . H2 H 0.2543(24) 0.2163(36) 0.0837(19) 0.050(9) Uiso 1 d . . C3 C 0.2733(3) 0.1891(4) -0.0418(2) 0.0607(9) Uani 1 d . . H3 H 0.2463(29) 0.0805(42) -0.0448(21) 0.068(10) Uiso 1 d . . C4 C 0.3028(3) 0.2615(5) -0.1118(2) 0.0599(9) Uani 1 d . . H4 H 0.3009(29) 0.2064(42) -0.1633(22) 0.075(11) Uiso 1 d . . C5 C 0.3731(3) 0.5221(5) -0.1716(2) 0.0594(9) Uani 1 d . . H5 H 0.3723(25) 0.4770(37) -0.2245(20) 0.057(9) Uiso 1 d . . C6 C 0.4051(3) 0.6786(5) -0.1551(2) 0.0590(9) Uani 1 d . . H6 H 0.4282(25) 0.7408(37) -0.1988(20) 0.059(9) Uiso 1 d . . C7 C 0.4048(3) 0.7550(4) -0.0743(2) 0.0498(7) Uani 1 d . . H7 H 0.4292(25) 0.8636(37) -0.0637(19) 0.052(9) Uiso 1 d . . C8 C 0.3697(2) 0.6678(3) -0.0112(2) 0.0397(6) Uani 1 d . . C9 C 0.3377(2) 0.5052(4) -0.0292(2) 0.0399(6) Uani 1 d . . C10 C 0.3379(2) 0.4261(4) -0.1075(2) 0.0500(8) Uani 1 d . . C11 C 0.3162(2) 0.5594(3) 0.1092(2) 0.0382(6) Uani 1 d . . C12 C 0.3546(2) 0.6971(3) 0.0780(2) 0.0372(6) Uani 1 d . . C13 C 0.4129(2) 0.6498(3) 0.2738(2) 0.0372(6) Uani 1 d . . C14 C 0.4494(2) 0.7878(3) 0.2449(2) 0.0395(6) Uani 1 d . . C15 C 0.4538(5) 0.3605(5) 0.3703(3) 0.0743(12) Uani 1 d . . H151 H 0.3783(46) 0.3616(63) 0.3756(33) 0.136(22) Uiso 1 d . . H152 H 0.4933(34) 0.3230(47) 0.4267(28) 0.093(13) Uiso 1 d . . H153 H 0.4735(53) 0.3097(76) 0.3191(42) 0.186(27) Uiso 1 d . . C16 C 0.5334(4) 0.9495(5) 0.4036(2) 0.0618(9) Uani 1 d . . H161 H 0.5807(30) 1.0400(45) 0.4270(23) 0.076(11) Uiso 1 d . . H162 H 0.5535(42) 0.8678(62) 0.4404(32) 0.130(20) Uiso 1 d . . H163 H 0.4502(40) 0.9778(52) 0.3914(28) 0.110(15) 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 S1 0.0442(4) 0.0569(5) 0.0345(4) 0.0028(3) 0.0093(3) -0.0114(3) S2 0.0610(5) 0.0378(4) 0.0397(4) 0.0024(3) 0.0123(3) -0.0004(3) S3 0.0797(6) 0.0516(5) 0.0406(4) 0.0055(4) -0.0087(4) -0.0030(4) S4 0.0524(5) 0.0628(5) 0.0527(5) -0.0139(4) 0.0142(4) -0.0173(4) C1 0.0319(13) 0.046(2) 0.0395(14) 0.0000(12) 0.0008(11) 0.0023(12) C2 0.042(2) 0.047(2) 0.055(2) 0.0007(15) 0.0037(14) -0.0017(14) C3 0.055(2) 0.050(2) 0.071(2) -0.016(2) 0.003(2) -0.001(2) C4 0.049(2) 0.070(2) 0.056(2) -0.024(2) 0.002(2) 0.011(2) C5 0.050(2) 0.096(3) 0.034(2) -0.007(2) 0.0123(14) 0.016(2) C6 0.056(2) 0.084(3) 0.041(2) 0.008(2) 0.0209(15) 0.007(2) C7 0.046(2) 0.059(2) 0.045(2) 0.0074(15) 0.0119(14) 0.004(2) C8 0.0338(14) 0.050(2) 0.0339(14) 0.0019(12) 0.0052(11) 0.0040(12) C9 0.0310(13) 0.054(2) 0.0336(13) -0.0002(12) 0.0046(11) 0.0053(12) C10 0.0366(15) 0.069(2) 0.042(2) -0.0091(15) 0.0043(12) 0.0122(14) C11 0.0355(13) 0.047(2) 0.0303(13) 0.0002(11) 0.0043(10) 0.0003(12) C12 0.0385(14) 0.0409(15) 0.0318(13) 0.0012(11) 0.0070(11) 0.0019(12) C13 0.0382(14) 0.042(2) 0.0317(13) -0.0004(11) 0.0083(11) 0.0025(12) C14 0.0409(15) 0.044(2) 0.0344(14) -0.0038(12) 0.0100(12) 0.0001(12) C15 0.095(3) 0.055(2) 0.063(3) 0.018(2) -0.002(2) -0.002(2) C16 0.071(3) 0.061(2) 0.051(2) -0.020(2) 0.010(2) -0.009(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 S1 C11 1.753(3) . ? S1 C13 1.780(3) . ? S2 C12 1.749(3) . ? S2 C14 1.782(3) . ? S3 C13 1.767(3) . ? S3 C15 1.774(4) . ? S4 C14 1.765(3) . ? S4 C16 1.807(4) . ? C1 C2 1.374(4) . ? C1 C9 1.418(4) . ? C1 C11 1.473(4) . ? C2 C3 1.424(5) . ? C2 H2 0.94(3) . ? C3 C4 1.371(5) . ? C3 H3 0.95(3) . ? C4 C10 1.426(5) . ? C4 H4 0.93(3) . ? C5 C6 1.362(5) . ? C5 C10 1.423(5) . ? C5 H5 0.91(3) . ? C6 C7 1.422(4) . ? C6 H6 0.95(3) . ? C7 C8 1.371(4) . ? C7 H7 0.95(3) . ? C8 C9 1.414(4) . ? C8 C12 1.476(3) . ? C9 C10 1.397(4) . ? C11 C12 1.364(4) . ? C13 C14 1.341(4) . ? C15 H151 0.92(5) . ? C15 H152 0.96(4) . ? C15 H153 0.98(6) . ? C16 H161 0.96(4) . ? C16 H162 0.89(5) . ? C16 H163 0.99(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 C13 99.04(12) . . ? C12 S2 C14 100.51(13) . . ? C13 S3 C15 105.7(2) . . ? C14 S4 C16 103.7(2) . . ? C2 C1 C9 119.2(3) . . ? C2 C1 C11 135.7(3) . . ? C9 C1 C11 105.1(2) . . ? C1 C2 C3 117.8(3) . . ? C1 C2 H2 123.0(18) . . ? C3 C2 H2 119.2(18) . . ? C4 C3 C2 122.8(3) . . ? C4 C3 H3 121.4(20) . . ? C2 C3 H3 115.7(21) . . ? C3 C4 C10 120.6(3) . . ? C3 C4 H4 121.8(22) . . ? C10 C4 H4 117.5(22) . . ? C6 C5 C10 121.0(3) . . ? C6 C5 H5 120.6(20) . . ? C10 C5 H5 118.4(20) . . ? C5 C6 C7 122.5(3) . . ? C5 C6 H6 119.7(19) . . ? C7 C6 H6 117.8(19) . . ? C8 C7 C6 118.6(3) . . ? C8 C7 H7 120.3(18) . . ? C6 C7 H7 121.1(18) . . ? C7 C8 C9 118.1(3) . . ? C7 C8 C12 136.7(3) . . ? C9 C8 C12 105.2(2) . . ? C10 C9 C8 124.8(3) . . ? C10 C9 C1 124.0(3) . . ? C8 C9 C1 111.2(2) . . ? C9 C10 C5 115.0(3) . . ? C9 C10 C4 115.6(3) . . ? C5 C10 C4 129.4(3) . . ? C12 C11 C1 109.3(2) . . ? C12 C11 S1 123.5(2) . . ? C1 C11 S1 127.1(2) . . ? C11 C12 C8 109.2(2) . . ? C11 C12 S2 123.4(2) . . ? C8 C12 S2 127.3(2) . . ? C14 C13 S3 120.0(2) . . ? C14 C13 S1 122.7(2) . . ? S3 C13 S1 117.3(2) . . ? C13 C14 S4 125.3(2) . . ? C13 C14 S2 123.7(2) . . ? S4 C14 S2 110.8(2) . . ? S3 C15 H151 100.7(34) . . ? S3 C15 H152 102.8(24) . . ? H151 C15 H152 101.7(38) . . ? S3 C15 H153 111.8(37) . . ? H151 C15 H153 119.9(49) . . ? H152 C15 H153 117.5(43) . . ? S4 C16 H161 106.0(21) . . ? S4 C16 H162 109.6(32) . . ? H161 C16 H162 107.5(36) . . ? S4 C16 H163 107.7(25) . . ? H161 C16 H163 111.2(32) . . ? H162 C16 H163 114.5(40) . . ? 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 C15 S3 C13 C14 -156.7(3) . . . . ? S3 C13 C14 S4 0.4(3) . . . . ? C13 C14 S4 C16 -58.4(3) . . . . ? _refine_diff_density_max 0.250 _refine_diff_density_min -0.378 _refine_diff_density_rms 0.055 #====================================================================END data_5:TCNQ _audit_creation_method SHELXL _chemical_name_systematic ; 8,9-di(methylsulfanyl)acenaphthyleno[1,2-b][1,4]dithiine 7,7,8,8-tetracyano-p-quinodimethane (1:1) ; _chemical_name_common ? _chemical_formula_moiety 'C12 H4 N4, C16 H12 S4' _chemical_formula_structural ? _chemical_formula_analytical ? _chemical_formula_sum 'C28 H16 N4 S4' _chemical_formula_weight 536.69 _chemical_melting_point 'not measured' _chemical_compound_source ? _ccdc_compound_id '5:TCNQ' _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' 'S' 'S' 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting 'Orthorhombic' _symmetry_space_group_name_H-M 'Pnma' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, -y, z+1/2' '-x, y+1/2, -z' 'x+1/2, -y+1/2, -z+1/2' '-x, -y, -z' 'x-1/2, y, -z-1/2' 'x, -y-1/2, z' '-x-1/2, y-1/2, z-1/2' _cell_length_a 19.451(1) _cell_length_b 18.738(1) _cell_length_c 6.883(1) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 2508.7(4) _cell_formula_units_Z 4 _cell_measurement_temperature 150(2) _cell_measurement_reflns_used 505 _cell_measurement_theta_min 10 _cell_measurement_theta_max 20 _exptl_crystal_description prism _exptl_crystal_colour black _exptl_crystal_size_max 0.44 _exptl_crystal_size_mid 0.16 _exptl_crystal_size_min 0.06 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.421 _exptl_crystal_density_method ? _exptl_crystal_F_000 1104 _exptl_absorpt_coefficient_mu 0.405 _exptl_absorpt_correction_type 'semi-empirical' _exptl_absorpt_correction_T_min 0.759 _exptl_absorpt_correction_T_max 0.978 _exptl_special_details ; Over a hemisphere of the reciprocal space scanned by \w scans in frames of 0.3\% \w, exposure time 30 seconds per frame. Absorption correction using SADABS program (G.M.Sheldrick, 1996); without it, R(int)=0.078. ; _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 'Siemens CCD area detector' _diffrn_measurement_method '\w scans' _diffrn_standards_number 0 _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 8339 _diffrn_reflns_av_R_equivalents 0.0547 _diffrn_reflns_av_sigmaI/netI 0.0510 _diffrn_reflns_limit_h_min -22 _diffrn_reflns_limit_h_max 17 _diffrn_reflns_limit_k_min -23 _diffrn_reflns_limit_k_max 24 _diffrn_reflns_limit_l_min -8 _diffrn_reflns_limit_l_max 6 _diffrn_reflns_theta_min 2.17 _diffrn_reflns_theta_max 25.00 _reflns_number_total 2185 _reflns_number_observed 1693 _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 'SHELXTL' _computing_publication_material 'SHELXTL' _refine_special_details ; Refinement on F^2^ for ALL reflections except for 32 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. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme 'calc w=1/[\s^2^(Fo^2^)+(0.0492P)^2^+4.9673P] 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 2153 _refine_ls_number_parameters 198 _refine_ls_number_restraints 1 _refine_ls_R_factor_all 0.0827 _refine_ls_R_factor_obs 0.0580 _refine_ls_wR_factor_all 0.1444 _refine_ls_wR_factor_obs 0.1275 _refine_ls_goodness_of_fit_all 1.128 _refine_ls_goodness_of_fit_obs 1.183 _refine_ls_restrained_S_all 1.165 _refine_ls_restrained_S_obs 1.184 _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 S1 S 0.54296(5) 0.66269(5) 0.22245(14) 0.0246(3) Uani 1 d . . S2 S 0.65861(5) 0.66830(5) -0.0726(2) 0.0316(3) Uani 1 d . . C1 C 0.3995(2) 0.6878(2) 0.1348(5) 0.0187(8) Uani 1 d . . C2 C 0.3682(2) 0.6221(2) 0.1140(6) 0.0242(9) Uani 1 d . . H2 H 0.3934(23) 0.5791(25) 0.1358(65) 0.045(13) Uiso 1 d . . C3 C 0.2973(2) 0.6204(2) 0.0679(6) 0.0277(10) Uani 1 d . . H3 H 0.2771(21) 0.5770(22) 0.0589(60) 0.030(11) Uiso 1 d . . C4 C 0.2585(2) 0.6813(2) 0.0466(6) 0.0257(9) Uani 1 d . . H4 H 0.2113(21) 0.6746(18) 0.0196(52) 0.015(10) Uiso 1 d . . C5 C 0.2894(3) 0.7500 0.0675(8) 0.0204(12) Uani 1 d S . C6 C 0.3591(3) 0.7500 0.1097(7) 0.0192(12) Uani 1 d S . C7 C 0.4689(2) 0.7136(2) 0.1826(5) 0.0175(8) Uani 1 d . . C8 C 0.6044(2) 0.7139(2) 0.0888(6) 0.0208(8) Uani 1 d . . C9 C 0.6603(3) 0.5783(2) 0.0198(9) 0.0412(13) Uani 1 d . . H91 H 0.6860(26) 0.5553(27) -0.0832(74) 0.051(15) Uiso 1 d . . H92 H 0.6822(26) 0.5789(25) 0.1412(77) 0.048(15) Uiso 1 d . . H93 H 0.6196(27) 0.5612(25) 0.0196(68) 0.042(15) Uiso 1 d . . C10 C 0.4222(2) 0.6743(2) 0.6387(5) 0.0215(8) Uani 1 d . . C11 C 0.4830(2) 0.7141(2) 0.6918(5) 0.0215(9) Uani 1 d D . H11 H 0.5263(14) 0.6864(16) 0.7254(50) 0.013(9) Uiso 1 d D . C12 C 0.3610(2) 0.7144(2) 0.5907(5) 0.0216(9) Uani 1 d . . H12 H 0.3216(21) 0.6926(19) 0.5675(55) 0.018(10) Uiso 1 d . . C13 C 0.4227(2) 0.6010(2) 0.6350(6) 0.0256(9) Uani 1 d . . C14 C 0.3647(2) 0.5590(2) 0.5801(7) 0.0317(10) Uani 1 d . . C15 C 0.4829(2) 0.5604(2) 0.6892(6) 0.0306(10) Uani 1 d . . N1 N 0.3192(2) 0.5233(2) 0.5372(7) 0.0446(11) Uani 1 d . . N2 N 0.5289(2) 0.5261(2) 0.7330(6) 0.0485(11) 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 S1 0.0222(6) 0.0232(5) 0.0286(5) 0.0070(4) 0.0028(4) 0.0038(4) S2 0.0224(6) 0.0311(5) 0.0413(6) -0.0040(5) 0.0089(5) 0.0057(4) C1 0.022(2) 0.021(2) 0.012(2) 0.0008(14) 0.003(2) 0.002(2) C2 0.028(3) 0.021(2) 0.024(2) 0.000(2) 0.003(2) -0.003(2) C3 0.027(3) 0.026(2) 0.029(2) -0.002(2) 0.002(2) -0.007(2) C4 0.020(3) 0.038(2) 0.019(2) -0.003(2) 0.001(2) -0.005(2) C5 0.018(3) 0.028(3) 0.014(3) 0.000 0.002(2) 0.000 C6 0.021(3) 0.022(2) 0.015(3) 0.000 0.004(2) 0.000 C7 0.015(2) 0.023(2) 0.014(2) 0.0017(14) 0.006(2) 0.0024(15) C8 0.012(2) 0.027(2) 0.024(2) 0.001(2) -0.001(2) 0.003(2) C9 0.029(3) 0.029(2) 0.065(4) -0.004(2) -0.005(3) 0.008(2) C10 0.023(2) 0.028(2) 0.013(2) 0.0043(15) 0.004(2) -0.002(2) C11 0.019(2) 0.029(2) 0.016(2) 0.002(2) -0.005(2) 0.000(2) C12 0.014(2) 0.033(2) 0.018(2) 0.002(2) 0.002(2) -0.003(2) C13 0.023(2) 0.031(2) 0.023(2) 0.006(2) 0.001(2) -0.001(2) C14 0.026(3) 0.029(2) 0.040(3) 0.010(2) -0.001(2) -0.003(2) C15 0.035(3) 0.027(2) 0.030(2) 0.001(2) -0.005(2) -0.005(2) N1 0.027(2) 0.034(2) 0.072(3) 0.012(2) -0.008(2) -0.007(2) N2 0.048(3) 0.035(2) 0.063(3) -0.002(2) -0.017(2) 0.009(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 S1 C7 1.749(4) . ? S1 C8 1.787(4) . ? S2 C8 1.753(4) . ? S2 C9 1.804(5) . ? C1 C2 1.381(5) . ? C1 C6 1.417(5) . ? C1 C7 1.470(5) . ? C2 C3 1.415(6) . ? C2 H2 0.95(5) . ? C3 C4 1.376(6) . ? C3 H3 0.91(4) . ? C4 C5 1.429(4) . ? C4 H4 0.94(4) . ? C5 C6 1.387(8) . ? C5 C4 1.429(4) 7_575 ? C6 C1 1.416(5) 7_575 ? C7 C7 1.365(7) 7_575 ? C8 C8 1.355(7) 7_575 ? C9 H91 0.97(5) . ? C9 H92 0.94(5) . ? C9 H93 0.85(5) . ? C10 C13 1.373(5) . ? C10 C12 1.446(5) . ? C10 C11 1.447(5) . ? C11 C11 1.345(7) 7_575 ? C11 H11 1.02(2) . ? C12 C12 1.334(8) 7_575 ? C12 H12 0.88(4) . ? C13 C14 1.427(6) . ? C13 C15 1.447(6) . ? C14 N1 1.147(5) . ? C15 N2 1.141(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 C7 S1 C8 100.2(2) . . ? C8 S2 C9 104.1(2) . . ? C2 C1 C6 118.4(4) . . ? C2 C1 C7 136.2(3) . . ? C6 C1 C7 105.4(3) . . ? C1 C2 C3 118.3(4) . . ? C1 C2 H2 120.6(28) . . ? C3 C2 H2 121.1(27) . . ? C4 C3 C2 122.7(4) . . ? C4 C3 H3 119.9(26) . . ? C2 C3 H3 117.3(26) . . ? C3 C4 C5 120.3(4) . . ? C3 C4 H4 116.5(21) . . ? C5 C4 H4 123.2(21) . . ? C6 C5 C4 115.7(3) . 7_575 ? C6 C5 C4 115.7(3) . . ? C4 C5 C4 128.7(5) 7_575 . ? C5 C6 C1 124.6(2) . 7_575 ? C5 C6 C1 124.6(2) . . ? C1 C6 C1 110.8(5) 7_575 . ? C7 C7 C1 109.2(2) 7_575 . ? C7 C7 S1 123.04(12) 7_575 . ? C1 C7 S1 127.7(3) . . ? C8 C8 S2 119.14(12) 7_575 . ? C8 C8 S1 122.43(12) 7_575 . ? S2 C8 S1 117.8(2) . . ? S2 C9 H91 99.5(29) . . ? S2 C9 H92 108.1(30) . . ? H91 C9 H92 115.1(42) . . ? S2 C9 H93 109.4(32) . . ? H91 C9 H93 108.2(44) . . ? H92 C9 H93 115.3(45) . . ? C13 C10 C12 121.5(4) . . ? C13 C10 C11 120.9(4) . . ? C12 C10 C11 117.6(3) . . ? C11 C11 C10 121.0(2) 7_575 . ? C11 C11 H11 120.7(19) 7_575 . ? C10 C11 H11 118.2(19) . . ? C12 C12 C10 121.3(2) 7_575 . ? C12 C12 H12 117.6(24) 7_575 . ? C10 C12 H12 121.0(24) . . ? C10 C13 C14 123.4(4) . . ? C10 C13 C15 121.8(4) . . ? C14 C13 C15 114.7(3) . . ? N1 C14 C13 177.9(4) . . ? N2 C15 C13 177.4(4) . . ? _refine_diff_density_max 0.614 _refine_diff_density_min -0.417 _refine_diff_density_rms 0.075 #====================================================================END data_5:Br2TCNQ _audit_creation_method SHELXL _chemical_name_systematic ; 8,9-di(methylsulfanyl)acenaphthyleno[1,2-b][1,4]dithiine 2,5-dibromo-7,7,8,8-tetracyano-p-quinodimethane (1:1) ; _chemical_name_common ? _chemical_formula_moiety 'C12 H4 N4, C16 H10 S4 Br2' _chemical_formula_structural ? _chemical_formula_analytical ? _chemical_formula_sum 'C28 H14 Br2 N4 S4' _chemical_formula_weight 694.49 _chemical_melting_point 'not measured' _chemical_compound_source ? _ccdc_compound_id '5:Br2TCNQ' _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' '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 7.848(1) _cell_length_b 10.295(1) _cell_length_c 17.309(1) _cell_angle_alpha 77.29(1) _cell_angle_beta 83.47(1) _cell_angle_gamma 89.59(1) _cell_volume 1355.1(2) _cell_formula_units_Z 2 _cell_measurement_temperature 150(2) _cell_measurement_reflns_used 512 _cell_measurement_theta_min 12 _cell_measurement_theta_max 20 _exptl_crystal_description 'plate' _exptl_crystal_colour 'black' _exptl_crystal_size_max 0.36 _exptl_crystal_size_mid 0.13 _exptl_crystal_size_min 0.08 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.702 _exptl_crystal_density_method ? _exptl_crystal_F_000 688 _exptl_absorpt_coefficient_mu 3.326 _exptl_absorpt_correction_type 'semiempirical' _exptl_absorpt_correction_T_min 0.5911 _exptl_absorpt_correction_T_max 0.9065 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 1.00 0.0400 0.00 -1.00 -1.00 0.0400 0.00 0.00 1.00 0.0650 0.00 0.00 -1.00 0.0650 -1.00 0.00 0.00 0.1800 1.00 0.00 0.00 0.1800 _exptl_special_details ; \w scans of 0.3\% \w each (exposure time 20 seconds per frame) nominally covered over a hemisphere of the reciprocal space. Semi-empirical absorption correction using SADABS program (G.M.Sheldrick, 1996). Without absorption correction, R(int)=0.086. From face-indexing (integration) absorption correction, T_min=0.4143, T_max=0.7878, R(int)=0.052. ; _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 'Siemens CCD area detector' _diffrn_measurement_method '\w scan in 0.3\% frames, 20 s/frame' _diffrn_standards_number 0 _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 13741 _diffrn_reflns_av_R_equivalents 0.0287 _diffrn_reflns_av_sigmaI/netI 0.0480 _diffrn_reflns_limit_h_min -11 _diffrn_reflns_limit_h_max 10 _diffrn_reflns_limit_k_min -14 _diffrn_reflns_limit_k_max 14 _diffrn_reflns_limit_l_min -23 _diffrn_reflns_limit_l_max 22 _diffrn_reflns_theta_min 2.03 _diffrn_reflns_theta_max 30.53 _reflns_number_total 7147 _reflns_number_observed 5664 _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 'SHELXTL Version 5/VMS' _computing_publication_material 'SHELXTL Version 5/VMS' _refine_special_details ; Refinement on F^2^ for ALL reflections except for 26 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. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme 'calc w=1/[\s^2^(Fo^2^)+(0.0191P)^2^+1.0675P] 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 0.0104(5) _refine_ls_extinction_expression 'Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^' _refine_ls_number_reflns 7121 _refine_ls_number_parameters 400 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0540 _refine_ls_R_factor_obs 0.0344 _refine_ls_wR_factor_all 0.0809 _refine_ls_wR_factor_obs 0.0671 _refine_ls_goodness_of_fit_all 1.108 _refine_ls_goodness_of_fit_obs 1.067 _refine_ls_restrained_S_all 1.137 _refine_ls_restrained_S_obs 1.067 _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 Br2 Br 0.46545(3) 0.43384(2) 0.38499(2) 0.02056(8) Uani 1 d . . Br5 Br 0.58345(4) 1.08612(2) 0.28033(2) 0.02336(8) Uani 1 d . . C01 C 0.6155(3) 0.6805(2) 0.2809(2) 0.0165(5) Uani 1 d . . C02 C 0.5018(3) 0.6202(2) 0.3518(2) 0.0172(5) Uani 1 d . . C03 C 0.4139(3) 0.6950(2) 0.3974(2) 0.0177(5) Uani 1 d . . H03 H 0.3390(36) 0.6553(28) 0.4445(18) 0.017(7) Uiso 1 d . . C04 C 0.4303(3) 0.8389(2) 0.3812(2) 0.0165(5) Uani 1 d . . C05 C 0.5435(3) 0.9002(2) 0.3102(2) 0.0168(5) Uani 1 d . . C06 C 0.6276(3) 0.8252(2) 0.2637(2) 0.0185(5) Uani 1 d . . H06 H 0.6995(38) 0.8629(30) 0.2194(19) 0.022(8) Uiso 1 d . . C07 C 0.7100(3) 0.6146(2) 0.2293(2) 0.0181(5) Uani 1 d . . C08 C 0.3413(3) 0.9040(3) 0.4349(2) 0.0192(5) Uani 1 d . . C71 C 0.7294(3) 0.4728(3) 0.2375(2) 0.0221(6) Uani 1 d . . C72 C 0.8129(3) 0.6899(3) 0.1593(2) 0.0210(5) Uani 1 d . . C81 C 0.2314(4) 0.8314(3) 0.5027(2) 0.0225(6) Uani 1 d . . C82 C 0.3510(4) 1.0437(3) 0.4355(2) 0.0225(6) Uani 1 d . . N71 N 0.7626(3) 0.3644(3) 0.2372(2) 0.0320(6) Uani 1 d . . N72 N 0.8974(3) 0.7467(3) 0.1038(2) 0.0302(6) Uani 1 d . . N81 N 0.1411(3) 0.7782(2) 0.5574(2) 0.0319(6) Uani 1 d . . N82 N 0.3492(4) 1.1488(3) 0.4473(2) 0.0354(6) Uani 1 d . . S1 S 0.32361(9) 0.51326(7) 0.17628(4) 0.02236(15) Uani 1 d . . S2 S 0.40237(9) 0.82997(7) 0.09321(4) 0.0252(2) Uani 1 d . . S3 S 0.27400(11) 0.46394(9) 0.01657(5) 0.0345(2) Uani 1 d . . S4 S 0.34917(11) 0.77511(8) -0.06411(5) 0.0330(2) Uani 1 d . . C1 C 0.1133(3) 0.6325(3) 0.2891(2) 0.0185(5) Uani 1 d . . C2 C 0.0326(3) 0.5299(3) 0.3464(2) 0.0217(5) Uani 1 d . . H2 H 0.0420(37) 0.4393(31) 0.3441(18) 0.021(8) Uiso 1 d . . C3 C -0.0763(4) 0.5643(3) 0.4106(2) 0.0257(6) Uani 1 d . . H3 H -0.1314(45) 0.4893(36) 0.4496(22) 0.040(10) Uiso 1 d . . C4 C -0.1022(4) 0.6933(3) 0.4180(2) 0.0259(6) Uani 1 d . . H4 H -0.1716(48) 0.7127(38) 0.4629(24) 0.049(11) Uiso 1 d . . C5 C -0.0308(4) 0.9411(3) 0.3557(2) 0.0290(7) Uani 1 d . . H5 H -0.0956(42) 0.9692(33) 0.4002(21) 0.033(9) Uiso 1 d . . C6 C 0.0553(4) 1.0316(3) 0.2927(2) 0.0308(7) Uani 1 d . . H6 H 0.0448(44) 1.1245(37) 0.2929(22) 0.041(10) Uiso 1 d . . C7 C 0.1595(4) 0.9917(3) 0.2295(2) 0.0266(6) Uani 1 d . . H7 H 0.2195(41) 1.0595(33) 0.1865(20) 0.031(9) Uiso 1 d . . C8 C 0.1744(3) 0.8580(3) 0.2318(2) 0.0203(5) Uani 1 d . . C9 C 0.0841(3) 0.7654(3) 0.2965(2) 0.0189(5) Uani 1 d . . C10 C -0.0194(3) 0.8013(3) 0.3592(2) 0.0232(6) Uani 1 d . . C11 C 0.2355(3) 0.6434(3) 0.2167(2) 0.0180(5) Uani 1 d . . C12 C 0.2697(3) 0.7751(3) 0.1827(2) 0.0189(5) Uani 1 d . . C13 C 0.3107(3) 0.5823(3) 0.0729(2) 0.0214(5) Uani 1 d . . C14 C 0.3429(3) 0.7110(3) 0.0393(2) 0.0229(6) Uani 1 d . . C15 C 0.1115(6) 0.3554(5) 0.0782(3) 0.0480(11) Uani 1 d . . H151 H 0.1455(65) 0.3161(51) 0.1243(34) 0.085(18) Uiso 1 d . . H152 H 0.0166(78) 0.4066(61) 0.0886(36) 0.109(22) Uiso 1 d . . H153 H 0.0899(64) 0.2981(53) 0.0513(33) 0.088(17) Uiso 1 d . . C16 C 0.2017(5) 0.9120(4) -0.0666(2) 0.0359(8) Uani 1 d . . H161 H 0.2614(46) 0.9934(37) -0.0595(22) 0.043(10) Uiso 1 d . . H162 H 0.1025(49) 0.8831(37) -0.0295(24) 0.046(11) Uiso 1 d . . H163 H 0.1623(51) 0.9328(40) -0.1200(26) 0.057(12) 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 Br2 0.02607(14) 0.01177(12) 0.02244(15) -0.00270(9) 0.00108(11) 0.00000(9) Br5 0.0319(2) 0.01222(13) 0.02380(15) -0.00335(10) 0.00466(11) -0.00210(10) C01 0.0162(11) 0.0158(12) 0.0177(13) -0.0031(9) -0.0037(10) -0.0009(9) C02 0.0185(12) 0.0137(11) 0.0201(13) -0.0035(9) -0.0054(10) -0.0005(9) C03 0.0198(12) 0.0149(12) 0.0182(13) -0.0037(10) -0.0011(10) -0.0020(10) C04 0.0178(12) 0.0165(12) 0.0152(12) -0.0036(9) -0.0023(10) -0.0011(9) C05 0.0190(12) 0.0118(11) 0.0192(13) -0.0026(9) -0.0028(10) -0.0003(9) C06 0.0215(13) 0.0143(12) 0.0183(13) -0.0020(10) 0.0009(11) -0.0032(10) C07 0.0192(12) 0.0161(12) 0.0200(13) -0.0055(10) -0.0030(10) -0.0001(9) C08 0.0216(13) 0.0164(12) 0.0192(13) -0.0035(10) -0.0011(10) -0.0016(10) C71 0.0226(13) 0.0222(14) 0.0223(14) -0.0081(11) 0.0000(11) 0.0017(10) C72 0.0232(13) 0.0174(12) 0.0240(14) -0.0084(11) -0.0026(11) 0.0026(10) C81 0.0288(14) 0.0196(13) 0.0211(14) -0.0105(11) 0.0010(12) 0.0010(11) C82 0.0266(14) 0.0179(13) 0.0222(14) -0.0053(10) 0.0026(11) -0.0007(10) N71 0.0380(15) 0.0240(13) 0.034(2) -0.0110(11) 0.0042(12) 0.0026(11) N72 0.0308(13) 0.0301(14) 0.0278(14) -0.0062(11) 0.0042(11) 0.0003(11) N81 0.0406(15) 0.0253(13) 0.0280(14) -0.0068(11) 0.0065(12) -0.0017(11) N82 0.051(2) 0.0228(13) 0.032(2) -0.0123(11) 0.0114(13) -0.0055(12) S1 0.0263(3) 0.0210(3) 0.0219(4) -0.0091(3) -0.0034(3) 0.0045(3) S2 0.0265(3) 0.0273(4) 0.0212(3) -0.0064(3) 0.0024(3) -0.0077(3) S3 0.0377(4) 0.0411(5) 0.0290(4) -0.0226(4) 0.0077(3) -0.0097(4) S4 0.0403(4) 0.0393(4) 0.0175(4) -0.0058(3) 0.0034(3) -0.0029(3) C1 0.0173(12) 0.0210(13) 0.0186(13) -0.0070(10) -0.0031(10) 0.0000(10) C2 0.0230(13) 0.0232(14) 0.0205(14) -0.0066(11) -0.0052(11) -0.0021(11) C3 0.0225(14) 0.034(2) 0.0197(14) -0.0042(12) -0.0035(11) -0.0029(12) C4 0.0214(13) 0.037(2) 0.0214(15) -0.0121(12) -0.0019(11) 0.0015(12) C5 0.0270(15) 0.033(2) 0.033(2) -0.0195(14) -0.0060(13) 0.0106(12) C6 0.034(2) 0.0243(15) 0.039(2) -0.0147(13) -0.0093(14) 0.0088(12) C7 0.0299(15) 0.0206(14) 0.031(2) -0.0070(12) -0.0079(13) 0.0022(12) C8 0.0205(13) 0.0216(13) 0.0203(13) -0.0055(10) -0.0072(11) 0.0018(10) C9 0.0180(12) 0.0221(13) 0.0187(13) -0.0071(10) -0.0054(10) 0.0010(10) C10 0.0185(13) 0.0301(15) 0.0243(15) -0.0119(12) -0.0046(11) 0.0045(11) C11 0.0179(12) 0.0199(12) 0.0174(13) -0.0071(10) -0.0020(10) 0.0018(10) C12 0.0179(12) 0.0220(13) 0.0170(13) -0.0057(10) -0.0005(10) -0.0020(10) C13 0.0182(12) 0.0290(14) 0.0195(14) -0.0123(11) 0.0006(10) 0.0002(10) C14 0.0207(13) 0.0294(15) 0.0198(14) -0.0098(11) 0.0019(11) -0.0006(11) C15 0.065(3) 0.048(2) 0.033(2) -0.015(2) 0.002(2) -0.027(2) C16 0.038(2) 0.034(2) 0.030(2) 0.0043(14) -0.005(2) -0.0049(15) _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 C02 1.892(2) . ? Br5 C05 1.888(2) . ? C01 C07 1.385(3) . ? C01 C02 1.453(4) . ? C01 C06 1.455(3) . ? C02 C03 1.353(4) . ? C03 C04 1.450(3) . ? C03 H03 0.96(3) . ? C04 C08 1.387(4) . ? C04 C05 1.455(3) . ? C05 C06 1.350(4) . ? C06 H06 0.91(3) . ? C07 C71 1.444(4) . ? C07 C72 1.447(4) . ? C08 C81 1.439(4) . ? C08 C82 1.444(4) . ? C71 N71 1.146(4) . ? C72 N72 1.148(4) . ? C81 N81 1.150(4) . ? C82 N82 1.143(3) . ? S1 C11 1.747(3) . ? S1 C13 1.788(3) . ? S2 C12 1.749(3) . ? S2 C14 1.788(3) . ? S3 C13 1.763(3) . ? S3 C15 1.789(4) . ? S4 C14 1.762(3) . ? S4 C16 1.813(4) . ? C1 C2 1.381(4) . ? C1 C9 1.417(4) . ? C1 C11 1.473(4) . ? C2 C3 1.429(4) . ? C2 H2 0.94(3) . ? C3 C4 1.373(4) . ? C3 H3 0.97(4) . ? C4 C10 1.433(4) . ? C4 H4 0.95(4) . ? C5 C6 1.382(5) . ? C5 C10 1.430(4) . ? C5 H5 0.97(3) . ? C6 C7 1.422(4) . ? C6 H6 0.96(4) . ? C7 C8 1.373(4) . ? C7 H7 0.98(3) . ? C8 C9 1.422(4) . ? C8 C12 1.475(4) . ? C9 C10 1.395(4) . ? C11 C12 1.369(4) . ? C13 C14 1.338(4) . ? C15 H151 0.88(6) . ? C15 H152 0.93(6) . ? C15 H153 0.86(5) . ? C16 H161 1.00(4) . ? C16 H162 0.95(4) . ? C16 H163 0.99(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 C07 C01 C02 126.7(2) . . ? C07 C01 C06 118.1(2) . . ? C02 C01 C06 115.2(2) . . ? C03 C02 C01 121.5(2) . . ? C03 C02 Br2 116.1(2) . . ? C01 C02 Br2 122.3(2) . . ? C02 C03 C04 123.0(2) . . ? C02 C03 H03 121.7(17) . . ? C04 C03 H03 115.3(17) . . ? C08 C04 C03 117.6(2) . . ? C08 C04 C05 126.6(2) . . ? C03 C04 C05 115.8(2) . . ? C06 C05 C04 120.9(2) . . ? C06 C05 Br5 117.2(2) . . ? C04 C05 Br5 121.8(2) . . ? C05 C06 C01 123.5(2) . . ? C05 C06 H06 121.4(19) . . ? C01 C06 H06 115.1(19) . . ? C01 C07 C71 128.0(2) . . ? C01 C07 C72 119.9(2) . . ? C71 C07 C72 112.0(2) . . ? C04 C08 C81 121.0(2) . . ? C04 C08 C82 127.4(2) . . ? C81 C08 C82 111.5(2) . . ? N71 C71 C07 171.4(3) . . ? N72 C72 C07 178.1(3) . . ? N81 C81 C08 177.2(3) . . ? N82 C82 C08 170.1(3) . . ? C11 S1 C13 99.58(13) . . ? C12 S2 C14 99.74(12) . . ? C13 S3 C15 104.0(2) . . ? C14 S4 C16 101.1(2) . . ? C2 C1 C9 118.9(2) . . ? C2 C1 C11 136.0(2) . . ? C9 C1 C11 105.1(2) . . ? C1 C2 C3 117.7(3) . . ? C1 C2 H2 123.4(18) . . ? C3 C2 H2 118.8(18) . . ? C4 C3 C2 123.2(3) . . ? C4 C3 H3 121.6(21) . . ? C2 C3 H3 115.2(21) . . ? C3 C4 C10 120.0(3) . . ? C3 C4 H4 121.0(23) . . ? C10 C4 H4 118.9(23) . . ? C6 C5 C10 120.5(3) . . ? C6 C5 H5 121.7(20) . . ? C10 C5 H5 117.8(20) . . ? C5 C6 C7 122.5(3) . . ? C5 C6 H6 117.7(22) . . ? C7 C6 H6 119.8(22) . . ? C8 C7 C6 118.3(3) . . ? C8 C7 H7 122.2(19) . . ? C6 C7 H7 119.6(19) . . ? C7 C8 C9 118.9(3) . . ? C7 C8 C12 136.2(3) . . ? C9 C8 C12 104.8(2) . . ? C10 C9 C1 124.4(3) . . ? C10 C9 C8 124.2(3) . . ? C1 C9 C8 111.4(2) . . ? C9 C10 C5 115.6(3) . . ? C9 C10 C4 115.8(3) . . ? C5 C10 C4 128.6(3) . . ? C12 C11 C1 109.3(2) . . ? C12 C11 S1 123.4(2) . . ? C1 C11 S1 127.2(2) . . ? C11 C12 C8 109.4(2) . . ? C11 C12 S2 123.3(2) . . ? C8 C12 S2 127.3(2) . . ? C14 C13 S3 122.4(2) . . ? C14 C13 S1 122.8(2) . . ? S3 C13 S1 114.4(2) . . ? C13 C14 S4 122.5(2) . . ? C13 C14 S2 123.4(2) . . ? S4 C14 S2 113.8(2) . . ? S3 C15 H151 112.0(34) . . ? S3 C15 H152 108.0(36) . . ? H151 C15 H152 107.7(47) . . ? S3 C15 H153 105.5(35) . . ? H151 C15 H153 111.0(47) . . ? H152 C15 H153 112.7(48) . . ? S4 C16 H161 110.8(21) . . ? S4 C16 H162 109.3(23) . . ? H161 C16 H162 115.3(31) . . ? S4 C16 H163 107.2(23) . . ? H161 C16 H163 107.6(31) . . ? H162 C16 H163 106.4(32) . . ? 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 C15 S3 C13 C14 -142.6(3) . . . . ? S3 C13 C14 S4 0.8(4) . . . . ? C13 C14 S4 C16 127.5(3) . . . . ? _refine_diff_density_max 0.490 _refine_diff_density_min -0.522 _refine_diff_density_rms 0.091 #====================================================================END data_5(I7) _audit_creation_method SHELXL _chemical_name_systematic ; 8,9-di(methylsulfanyl)acenaphthyleno[1,2-b][1,4]dithiine bis(diiodine) triiodide ; _chemical_name_common ? _chemical_formula_moiety 'C16 H12 S4 1+, I3 1-, 2(I2)' _chemical_formula_structural ? _chemical_formula_analytical ? _chemical_formula_sum 'C16 H12 I7 S4' _chemical_formula_weight 1220.80 _chemical_melting_point ? _chemical_compound_source ? _ccdc_compound_id '5(I7)' _ccdc_biological_activity '?' _ccdc_polymorph '?' _ccdc_disorder ; One iodine atom is disordered over 2 positions, I(1) and I(1'), with occupancies of 90 and 10%, 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' '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 10.420(1) _cell_length_b 11.263(1) _cell_length_c 13.087(1) _cell_angle_alpha 64.76(1) _cell_angle_beta 78.80(1) _cell_angle_gamma 79.74(1) _cell_volume 1354.9(2) _cell_formula_units_Z 2 _cell_measurement_temperature 150(2) _cell_measurement_reflns_used 512 _cell_measurement_theta_min 12 _cell_measurement_theta_max 20 _exptl_crystal_description rhombohedron _exptl_crystal_colour black _exptl_crystal_size_max 0.30 _exptl_crystal_size_mid 0.17 _exptl_crystal_size_min 0.15 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 2.992 _exptl_crystal_density_method ? _exptl_crystal_F_000 1086 _exptl_absorpt_coefficient_mu 8.330 _exptl_absorpt_correction_type 'semi-empirical' _exptl_absorpt_correction_T_min 0.2586 _exptl_absorpt_correction_T_max 0.4191 _exptl_special_details ; Full sphere of the reciprocal space was scanned in frames of 0.3\% \w, exposure time 10 second per frame. Absorption correction with SADABS program (G.M.Sheldrick, 1996); without correction, R(int)=0.139. ; _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 'Siemens CCD area detector' _diffrn_measurement_method '\w scans' _diffrn_standards_number 212 _diffrn_standards_interval_count ? _diffrn_standards_interval_time '16 h' _diffrn_standards_decay_% 0.1 _diffrn_reflns_number 17175 _diffrn_reflns_av_R_equivalents 0.0346 _diffrn_reflns_av_sigmaI/netI 0.0457 _diffrn_reflns_limit_h_min -14 _diffrn_reflns_limit_h_max 13 _diffrn_reflns_limit_k_min -15 _diffrn_reflns_limit_k_max 15 _diffrn_reflns_limit_l_min -17 _diffrn_reflns_limit_l_max 18 _diffrn_reflns_theta_min 1.74 _diffrn_reflns_theta_max 30.25 _reflns_number_total 7267 _reflns_number_observed 5770 _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 'SHELXTL' _computing_publication_material 'SHELXTL' _refine_special_details ; Refinement on F^2^ for ALL reflections except for 5 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. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme 'calc w=1/[\s^2^(Fo^2^)+(0.0398P)^2^+3.6829P] 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 constr _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 7262 _refine_ls_number_parameters 252 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0569 _refine_ls_R_factor_obs 0.0395 _refine_ls_wR_factor_all 0.0992 _refine_ls_wR_factor_obs 0.0881 _refine_ls_goodness_of_fit_all 1.104 _refine_ls_goodness_of_fit_obs 1.109 _refine_ls_restrained_S_all 1.108 _refine_ls_restrained_S_obs 1.109 _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 0.87969(7) -0.21339(7) 1.04910(5) 0.03657(14) Uani 0.90 d P 1 I1' I 0.9159(6) -0.1832(7) 1.0414(6) 0.038(2) Uiso 0.10 d P 2 I2 I 0.70233(4) 0.00892(4) 1.02836(4) 0.02958(10) Uani 1 d . . I3 I 0.50166(4) 0.25991(4) 1.01423(4) 0.03232(11) Uani 1 d . . I4 I 0.72318(4) 0.42545(4) 0.91662(3) 0.02676(10) Uani 1 d . . I5 I 0.94680(5) 0.57517(4) 0.82475(4) 0.03602(11) Uani 1 d . . I6 I 0.95620(4) 0.67266(4) 0.54641(4) 0.03046(10) Uani 1 d . . I7 I 0.97273(5) 0.74885(4) 0.31550(4) 0.03747(12) Uani 1 d . . S1 S 0.37696(14) 0.14726(14) 0.35169(12) 0.0222(3) Uani 1 d . . S2 S 0.34765(14) 0.03930(14) 0.64780(12) 0.0215(3) Uani 1 d . . S3 S 0.18735(15) -0.0449(2) 0.40523(13) 0.0252(3) Uani 1 d . . S4 S 0.15931(14) -0.13133(15) 0.65355(13) 0.0246(3) Uani 1 d . . C1 C 0.5307(5) 0.3128(5) 0.3737(5) 0.0204(11) Uani 1 d . . C2 C 0.5788(6) 0.3909(6) 0.2630(6) 0.0256(12) Uani 1 d . . H2 H 0.5535(6) 0.3840(6) 0.2001(6) 0.031 Uiso 1 d R . C3 C 0.6678(6) 0.4821(6) 0.2465(6) 0.0283(13) Uani 1 d . . H3 H 0.7027(6) 0.5353(6) 0.1709(6) 0.034 Uiso 1 d R . C4 C 0.7053(6) 0.4962(6) 0.3364(6) 0.0287(13) Uani 1 d . . H4 H 0.7654(6) 0.5577(6) 0.3216(6) 0.034 Uiso 1 d R . C5 C 0.6792(6) 0.4192(6) 0.5542(6) 0.0298(14) Uani 1 d . . H5 H 0.7370(6) 0.4778(6) 0.5504(6) 0.036 Uiso 1 d R . C6 C 0.6210(6) 0.3359(7) 0.6592(6) 0.0300(14) Uani 1 d . . H6 H 0.6402(6) 0.3394(7) 0.7259(6) 0.036 Uiso 1 d R . C7 C 0.5342(6) 0.2455(6) 0.6717(5) 0.0234(12) Uani 1 d . . H7 H 0.4947(6) 0.1899(6) 0.7446(5) 0.028 Uiso 1 d R . C8 C 0.5096(5) 0.2420(5) 0.5724(5) 0.0213(11) Uani 1 d . . C9 C 0.5685(5) 0.3285(6) 0.4655(5) 0.0224(11) Uani 1 d . . C10 C 0.6534(6) 0.4180(6) 0.4521(6) 0.0276(13) Uani 1 d . . C11 C 0.4431(5) 0.2077(5) 0.4281(5) 0.0197(11) Uani 1 d . . C12 C 0.4323(5) 0.1654(5) 0.5454(5) 0.0195(11) Uani 1 d . . C13 C 0.2810(5) 0.0284(5) 0.4554(5) 0.0208(11) Uani 1 d . . C14 C 0.2692(5) -0.0122(5) 0.5713(5) 0.0203(11) Uani 1 d . . C15 C 0.2194(7) 0.0388(7) 0.2524(6) 0.0339(15) Uani 1 d . . H151 H 0.1633(36) 0.0096(37) 0.2173(6) 0.050(14) Uiso 1 d R . H152 H 0.3120(14) 0.0180(39) 0.2267(7) 0.050(14) Uiso 1 d R . H153 H 0.2001(46) 0.1343(8) 0.2299(6) 0.050(14) Uiso 1 d R . C16 C 0.1684(7) -0.1574(7) 0.7980(5) 0.0320(14) Uani 1 d . . H161 H 0.2589(12) -0.1896(45) 0.8149(14) 0.046(13) Uiso 1 d R . H162 H 0.1094(36) -0.2229(36) 0.8507(6) 0.046(13) Uiso 1 d R . H163 H 0.1419(46) -0.0740(12) 0.8068(12) 0.046(13) Uiso 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 I1 0.0407(3) 0.0353(3) 0.0284(3) -0.0106(2) -0.0007(2) -0.0010(3) I2 0.0365(2) 0.0302(2) 0.0224(2) -0.0098(2) -0.0004(2) -0.0106(2) I3 0.0307(2) 0.0282(2) 0.0333(2) -0.0090(2) 0.0006(2) -0.0058(2) I4 0.0327(2) 0.0216(2) 0.0238(2) -0.00777(15) -0.0049(2) -0.00004(15) I5 0.0396(2) 0.0312(2) 0.0391(3) -0.0141(2) -0.0019(2) -0.0125(2) I6 0.0273(2) 0.0228(2) 0.0405(3) -0.0124(2) -0.0041(2) -0.00257(15) I7 0.0417(2) 0.0278(2) 0.0389(3) -0.0111(2) -0.0069(2) 0.0013(2) S1 0.0248(7) 0.0230(7) 0.0166(7) -0.0056(5) -0.0013(5) -0.0052(5) S2 0.0223(6) 0.0252(7) 0.0169(7) -0.0079(5) 0.0002(5) -0.0071(5) S3 0.0276(7) 0.0271(7) 0.0224(7) -0.0086(6) -0.0049(6) -0.0088(6) S4 0.0251(7) 0.0255(7) 0.0205(7) -0.0046(6) -0.0019(6) -0.0096(6) C1 0.018(2) 0.015(2) 0.026(3) -0.007(2) -0.002(2) 0.002(2) C2 0.018(3) 0.025(3) 0.028(3) -0.006(2) -0.004(2) 0.001(2) C3 0.026(3) 0.022(3) 0.027(3) -0.001(2) -0.002(2) -0.003(2) C4 0.022(3) 0.018(3) 0.041(4) -0.008(3) 0.000(3) -0.004(2) C5 0.028(3) 0.026(3) 0.039(4) -0.016(3) -0.006(3) -0.002(2) C6 0.031(3) 0.035(3) 0.033(4) -0.020(3) -0.008(3) -0.003(3) C7 0.025(3) 0.019(3) 0.026(3) -0.009(2) -0.007(2) 0.001(2) C8 0.020(3) 0.017(2) 0.025(3) -0.006(2) -0.003(2) -0.003(2) C9 0.018(3) 0.021(3) 0.026(3) -0.010(2) -0.001(2) 0.001(2) C10 0.024(3) 0.019(3) 0.037(4) -0.009(3) -0.005(3) -0.001(2) C11 0.020(3) 0.021(3) 0.019(3) -0.008(2) -0.004(2) -0.003(2) C12 0.018(2) 0.019(3) 0.018(3) -0.006(2) -0.001(2) -0.002(2) C13 0.021(3) 0.016(2) 0.023(3) -0.007(2) -0.003(2) -0.001(2) C14 0.020(3) 0.018(3) 0.021(3) -0.006(2) 0.000(2) -0.003(2) C15 0.045(4) 0.038(4) 0.022(3) -0.009(3) -0.009(3) -0.016(3) C16 0.040(4) 0.036(4) 0.017(3) -0.005(3) 0.001(3) -0.018(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 I1 I2 2.7795(8) . ? I1' I2 2.789(7) . ? I2 I3 3.1617(7) . ? I3 I4 2.9652(7) . ? I4 I5 2.8811(7) . ? I5 I6 3.3125(7) . ? I6 I7 2.7453(7) . ? S1 C11 1.718(6) . ? S1 C13 1.742(6) . ? S2 C12 1.719(6) . ? S2 C14 1.729(6) . ? S3 C13 1.750(6) . ? S3 C15 1.802(7) . ? S4 C14 1.763(6) . ? S4 C16 1.804(6) . ? C1 C2 1.383(8) . ? C1 C9 1.421(8) . ? C1 C11 1.468(8) . ? C2 C3 1.426(9) . ? C3 C4 1.386(10) . ? C4 C10 1.441(9) . ? C5 C6 1.385(10) . ? C5 C10 1.419(9) . ? C6 C7 1.418(8) . ? C7 C8 1.390(8) . ? C8 C9 1.414(8) . ? C8 C12 1.461(8) . ? C9 C10 1.391(8) . ? C11 C12 1.388(8) . ? C13 C14 1.371(8) . ? 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 177.84(2) . . ? I1' I2 I3 168.68(13) . . ? I4 I3 I2 89.37(2) . . ? I5 I4 I3 177.32(2) . . ? I4 I5 I6 102.66(2) . . ? I7 I6 I5 177.99(2) . . ? C11 S1 C13 103.9(3) . . ? C12 S2 C14 104.3(3) . . ? C13 S3 C15 104.2(3) . . ? C14 S4 C16 103.5(3) . . ? C2 C1 C9 119.3(5) . . ? C2 C1 C11 135.7(6) . . ? C9 C1 C11 104.9(5) . . ? C1 C2 C3 117.9(6) . . ? C4 C3 C2 122.6(6) . . ? C3 C4 C10 120.2(6) . . ? C6 C5 C10 120.6(6) . . ? C5 C6 C7 122.9(6) . . ? C8 C7 C6 117.0(6) . . ? C7 C8 C9 119.6(5) . . ? C7 C8 C12 135.5(5) . . ? C9 C8 C12 104.9(5) . . ? C10 C9 C8 124.0(6) . . ? C10 C9 C1 124.2(6) . . ? C8 C9 C1 111.9(5) . . ? C9 C10 C5 115.9(6) . . ? C9 C10 C4 115.8(6) . . ? C5 C10 C4 128.3(6) . . ? C12 C11 C1 108.7(5) . . ? C12 C11 S1 128.6(4) . . ? C1 C11 S1 122.6(4) . . ? C11 C12 C8 109.6(5) . . ? C11 C12 S2 127.2(4) . . ? C8 C12 S2 123.2(4) . . ? C14 C13 S1 127.3(4) . . ? C14 C13 S3 116.7(4) . . ? S1 C13 S3 116.0(3) . . ? C13 C14 S2 128.3(4) . . ? C13 C14 S4 116.2(4) . . ? S2 C14 S4 115.4(3) . . ? _refine_diff_density_max 1.152 _refine_diff_density_min -1.886 _refine_diff_density_rms 0.222 #====================================================================END