Supplementary Material (ESI) for Photochemical & Photobiological Sciences This journal is © The Royal Society of Chemistry and Owner Societies 2006 data_global _journal_coden_Cambridge 171 loop_ _publ_author_name 'Jay Kochi' 'S. M. Dibrov' 'S.V. Rosokha' 'T.Y. Rosokha' _publ_contact_author_name 'Jay Kochi' _publ_contact_author_address ; Chemistry University of Houston 4800 Calhoun Rd Fleming Bldg Houston TX 77204 UNITED STATES OF AMERICA ; _publ_contact_author_email JKOCHI@UH.EDU _publ_requested_journal 'Photochemical & Photobiological Sciences' _publ_section_title ; Electronic Structures of Intermolecular Charge-Transfer States in Fast Electron Transfers with Tetrathiafulvalene Donor. Thermal and Photoactivation of [2+4] Cycloaddition to o-Chloranil Acceptor. ; data_vas2 _database_code_depnum_ccdc_archive 'CCDC 611965' _audit_creation_method SHELXL-97 _chemical_name_systematic ; tetrachloro-o-benzoquinone, beta form ; _chemical_name_common beta-oCA _chemical_melting_point ? _chemical_formula_moiety 'C6 Cl4 O2' _chemical_formula_sum 'C6 Cl4 O2' _chemical_formula_weight 245.86 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' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Cl Cl 0.1484 0.1585 '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 _symmetry_space_group_name_Hall '-P 2yn' 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 26.010(2) _cell_length_b 8.1572(6) _cell_length_c 28.795(2) _cell_angle_alpha 90.00 _cell_angle_beta 113.518(4) _cell_angle_gamma 90.00 _cell_volume 5601.9(7) _cell_formula_units_Z 28 _cell_measurement_temperature 173(2) _cell_measurement_reflns_used 188 _cell_measurement_theta_min 4.98 _cell_measurement_theta_max 20.77 _exptl_crystal_description plate _exptl_crystal_colour red _exptl_crystal_size_max 0.6 _exptl_crystal_size_mid 0.4 _exptl_crystal_size_min 0.2 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 2.041 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 3360 _exptl_absorpt_coefficient_mu 1.423 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details 'Semi-empirical (SADABS procedure)' _exptl_absorpt_correction_T_min 0.469 _exptl_absorpt_correction_T_max 0.752 _exptl_special_details ; ? ; _diffrn_ambient_temperature 173(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 SMART' _diffrn_measurement_method ; \w-scan, frame range 0.3 deg, hemisphere ; _diffrn_standards_number none _diffrn_standards_interval_count 0 _diffrn_standards_interval_time 0 _diffrn_standards_decay_% 0 _diffrn_reflns_number 48388 _diffrn_reflns_av_R_equivalents 0.0382 _diffrn_reflns_av_sigmaI/netI 0.0367 _diffrn_reflns_limit_h_min -37 _diffrn_reflns_limit_h_max 37 _diffrn_reflns_limit_k_min -11 _diffrn_reflns_limit_k_max 9 _diffrn_reflns_limit_l_min -31 _diffrn_reflns_limit_l_max 41 _diffrn_reflns_theta_min 0.89 _diffrn_reflns_theta_max 31.00 _reflns_number_total 16756 _reflns_number_gt 7532 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'SMART V5.630 (BrukerAXS, 1997-2001)' _computing_cell_refinement 'SAINT V6.28 (BrukerAXS, 1997-2001)' _computing_data_reduction 'SAINT & SADABS V2.06 (Sheldrick, 2000)' _computing_structure_solution 'SHELXTL v. 6.12 (Sheldrick, 2001)' _computing_structure_refinement 'SHELXTL v. 6.12 (Sheldrick, 2001)' _computing_molecular_graphics 'XP V5.06 (BrukerAXS, 1997-99)' _computing_publication_material 'SHELXL-93, XCIF V5.05 (BrukerAXS, 1997-99)' _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. 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 _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0876P)^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 16756 _refine_ls_number_parameters 757 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.1128 _refine_ls_R_factor_gt 0.0596 _refine_ls_wR_factor_ref 0.1888 _refine_ls_wR_factor_gt 0.1561 _refine_ls_goodness_of_fit_ref 0.989 _refine_ls_restrained_S_all 0.989 _refine_ls_shift/su_max 0.005 _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 C11 C 0.39297(14) 0.4264(4) 0.39284(12) 0.0227(8) Uani 1 1 d . . . C12 C 0.34444(13) 0.3988(5) 0.34053(13) 0.0232(8) Uani 1 1 d . . . C13 C 0.32959(13) 0.2277(4) 0.32378(12) 0.0203(8) Uani 1 1 d . . . C14 C 0.35852(13) 0.1025(4) 0.35279(11) 0.0174(7) Uani 1 1 d . . . C15 C 0.40644(13) 0.1285(4) 0.40172(11) 0.0169(7) Uani 1 1 d . . . C16 C 0.42211(14) 0.2806(4) 0.42094(12) 0.0210(8) Uani 1 1 d . . . O11 O 0.40420(11) 0.5654(3) 0.40874(10) 0.0358(7) Uani 1 1 d . . . O12 O 0.32175(11) 0.5171(3) 0.31536(10) 0.0354(7) Uani 1 1 d . . . Cl13 Cl 0.27456(4) 0.19762(14) 0.26732(3) 0.0353(2) Uani 1 1 d . . . Cl14 Cl 0.34080(3) -0.09656(11) 0.33481(3) 0.0261(2) Uani 1 1 d . . . Cl15 Cl 0.44150(4) -0.03847(11) 0.43447(3) 0.0274(2) Uani 1 1 d . . . Cl16 Cl 0.47528(4) 0.31597(12) 0.47857(3) 0.0315(2) Uani 1 1 d . . . C21 C 0.39255(14) 0.9251(4) 0.24462(12) 0.0214(8) Uani 1 1 d . . . C22 C 0.44131(14) 0.8989(5) 0.29677(12) 0.0222(8) Uani 1 1 d . . . C23 C 0.45651(13) 0.7273(5) 0.31395(12) 0.0210(8) Uani 1 1 d . . . C24 C 0.42747(13) 0.6021(4) 0.28507(11) 0.0177(7) Uani 1 1 d . . . C25 C 0.37878(12) 0.6275(4) 0.23662(11) 0.0166(7) Uani 1 1 d . . . C26 C 0.36270(14) 0.7791(4) 0.21720(12) 0.0185(7) Uani 1 1 d . . . O21 O 0.38112(11) 1.0634(3) 0.22860(9) 0.0323(7) Uani 1 1 d . . . O22 O 0.46490(11) 1.0170(3) 0.32144(10) 0.0349(7) Uani 1 1 d . . . Cl23 Cl 0.51126(4) 0.69897(14) 0.37099(3) 0.0354(3) Uani 1 1 d . . . Cl24 Cl 0.44608(4) 0.40357(11) 0.30342(3) 0.0262(2) Uani 1 1 d . . . Cl25 Cl 0.34387(4) 0.45919(11) 0.20438(3) 0.0274(2) Uani 1 1 d . . . Cl26 Cl 0.30835(4) 0.81264(12) 0.16028(3) 0.0311(2) Uani 1 1 d . . . C31 C 0.62600(13) 0.4038(5) 0.48307(13) 0.0242(8) Uani 1 1 d . . . C32 C 0.67356(13) 0.4306(4) 0.53615(12) 0.0206(8) Uani 1 1 d . . . C33 C 0.70207(14) 0.2846(4) 0.56420(12) 0.0193(7) Uani 1 1 d . . . C34 C 0.68640(13) 0.1329(4) 0.54499(11) 0.0171(7) Uani 1 1 d . . . C35 C 0.63939(13) 0.1061(4) 0.49549(11) 0.0185(7) Uani 1 1 d . . . C36 C 0.61129(13) 0.2321(4) 0.46541(12) 0.0203(8) Uani 1 1 d . . . O31 O 0.60374(11) 0.5215(3) 0.45763(10) 0.0375(7) Uani 1 1 d . . . O32 O 0.68455(11) 0.5693(3) 0.55200(9) 0.0341(7) Uani 1 1 d . . . Cl33 Cl 0.75534(4) 0.31925(12) 0.62188(3) 0.0293(2) Uani 1 1 d . . . Cl34 Cl 0.72081(4) -0.03493(10) 0.57810(3) 0.0253(2) Uani 1 1 d . . . Cl35 Cl 0.62136(4) -0.09266(11) 0.47747(3) 0.0262(2) Uani 1 1 d . . . Cl36 Cl 0.55813(4) 0.20245(13) 0.40792(3) 0.0348(2) Uani 1 1 d . . . C41 C 0.68364(14) 0.9319(4) 0.39652(12) 0.0224(8) Uani 1 1 d . . . C42 C 0.73015(14) 0.9038(5) 0.44975(12) 0.0243(8) Uani 1 1 d . . . C43 C 0.74529(14) 0.7324(4) 0.46641(12) 0.0239(9) Uani 1 1 d . . . C44 C 0.71677(13) 0.6069(4) 0.43640(12) 0.0203(8) Uani 1 1 d . . . C45 C 0.67014(13) 0.6348(4) 0.38668(11) 0.0190(8) Uani 1 1 d . . . C46 C 0.65503(14) 0.7857(4) 0.36746(12) 0.0221(8) Uani 1 1 d . . . O41 O 0.67252(11) 1.0705(3) 0.38070(9) 0.0345(7) Uani 1 1 d . . . O42 O 0.75232(12) 1.0209(3) 0.47516(9) 0.0366(7) Uani 1 1 d . . . Cl43 Cl 0.79840(4) 0.70096(13) 0.52357(3) 0.0346(2) Uani 1 1 d . . . Cl44 Cl 0.73429(4) 0.40722(11) 0.45421(3) 0.0275(2) Uani 1 1 d . . . Cl45 Cl 0.63576(4) 0.46682(11) 0.35311(3) 0.0279(2) Uani 1 1 d . . . Cl46 Cl 0.60272(4) 0.82194(12) 0.30945(3) 0.0310(2) Uani 1 1 d . . . C51 C 0.91866(14) 0.3962(5) 0.63185(13) 0.0254(8) Uani 1 1 d . . . C52 C 0.96818(14) 0.4234(5) 0.68358(12) 0.0229(8) Uani 1 1 d . . . C53 C 0.99820(13) 0.2768(4) 0.71059(12) 0.0203(8) Uani 1 1 d . . . C54 C 0.98220(13) 0.1249(4) 0.69102(12) 0.0204(8) Uani 1 1 d . . . C55 C 0.93333(13) 0.0989(5) 0.64267(12) 0.0221(8) Uani 1 1 d . . . C56 C 0.90303(14) 0.2250(5) 0.61444(12) 0.0255(9) Uani 1 1 d . . . O51 O 0.89499(11) 0.5139(3) 0.60763(10) 0.0401(8) Uani 1 1 d . . . O52 O 0.98001(11) 0.5602(3) 0.69959(10) 0.0367(7) Uani 1 1 d . . . Cl53 Cl 1.05269(4) 0.30949(12) 0.76759(3) 0.0312(2) Uani 1 1 d . . . Cl54 Cl 1.01775(4) -0.04367(11) 0.72301(3) 0.0300(2) Uani 1 1 d . . . Cl55 Cl 0.91496(4) -0.09985(12) 0.62486(3) 0.0300(2) Uani 1 1 d . . . Cl56 Cl 0.84747(4) 0.19589(14) 0.55902(3) 0.0395(3) Uani 1 1 d . . . C61 C 1.01067(15) 0.8957(5) 0.58097(14) 0.0311(9) Uani 1 1 d . . . C62 C 0.96076(16) 0.9228(5) 0.52920(14) 0.0298(9) Uani 1 1 d . . . C63 C 0.93071(15) 0.7763(5) 0.50254(13) 0.0272(9) Uani 1 1 d . . . C64 C 0.94715(15) 0.6247(5) 0.52188(13) 0.0269(9) Uani 1 1 d . . . C65 C 0.99614(15) 0.5994(5) 0.56984(13) 0.0269(9) Uani 1 1 d . . . C66 C 1.02576(16) 0.7255(5) 0.59793(14) 0.0307(10) Uani 1 1 d . . . O61 O 1.03443(12) 1.0147(4) 0.60443(10) 0.0419(8) Uani 1 1 d . . . O62 O 0.94932(12) 1.0596(3) 0.51283(10) 0.0408(8) Uani 1 1 d . . . Cl63 Cl 0.87572(4) 0.80867(13) 0.44575(3) 0.0354(3) Uani 1 1 d . . . Cl64 Cl 0.91121(4) 0.45603(12) 0.49012(3) 0.0344(3) Uani 1 1 d . . . Cl65 Cl 1.01483(4) 0.40041(13) 0.58790(3) 0.0336(2) Uani 1 1 d . . . Cl66 Cl 1.08194(4) 0.69623(15) 0.65374(3) 0.0409(3) Uani 1 1 d . . . C71 C 1.19713(15) 0.4043(5) 0.76495(13) 0.0260(8) Uani 1 1 d . . . C72 C 1.24341(15) 0.4329(5) 0.81885(13) 0.0271(9) Uani 1 1 d . . . C73 C 1.27172(15) 0.2872(5) 0.84770(13) 0.0263(8) Uani 1 1 d . . . C74 C 1.25658(14) 0.1352(4) 0.82848(12) 0.0243(9) Uani 1 1 d . . . C75 C 1.21055(15) 0.1080(5) 0.77870(13) 0.0262(9) Uani 1 1 d . . . C76 C 1.18219(15) 0.2329(5) 0.74807(13) 0.0287(9) Uani 1 1 d . . . O71 O 1.17496(11) 0.5227(3) 0.73930(10) 0.0385(7) Uani 1 1 d . . . O72 O 1.25398(12) 0.5708(3) 0.83404(10) 0.0377(7) Uani 1 1 d . . . Cl73 Cl 1.32378(4) 0.32291(12) 0.90564(3) 0.0335(2) Uani 1 1 d . . . Cl74 Cl 1.29051(4) -0.03229(11) 0.86203(3) 0.0310(2) Uani 1 1 d . . . Cl75 Cl 1.19254(4) -0.09121(12) 0.76037(3) 0.0322(2) Uani 1 1 d . . . Cl76 Cl 1.12971(4) 0.20277(14) 0.69017(3) 0.0382(3) Uani 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 C11 0.0279(16) 0.0136(19) 0.0325(17) -0.0042(14) 0.0183(14) -0.0042(12) C12 0.0236(16) 0.0170(19) 0.0334(17) 0.0040(14) 0.0159(14) 0.0042(13) C13 0.0173(14) 0.022(2) 0.0232(15) -0.0013(13) 0.0094(13) -0.0030(12) C14 0.0200(15) 0.0150(17) 0.0208(14) -0.0047(12) 0.0119(12) -0.0071(12) C15 0.0205(14) 0.0123(17) 0.0209(14) -0.0014(12) 0.0114(12) -0.0043(11) C16 0.0271(16) 0.0132(18) 0.0250(16) -0.0044(12) 0.0130(14) -0.0048(12) O11 0.0463(15) 0.0156(15) 0.0464(15) -0.0061(12) 0.0195(13) -0.0050(11) O12 0.0352(14) 0.0264(17) 0.0437(15) 0.0064(12) 0.0148(12) 0.0123(11) Cl13 0.0232(4) 0.0461(6) 0.0297(4) -0.0017(4) 0.0033(3) -0.0014(4) Cl14 0.0323(4) 0.0166(5) 0.0326(4) -0.0100(3) 0.0163(4) -0.0109(3) Cl15 0.0379(4) 0.0143(4) 0.0277(4) 0.0027(3) 0.0109(3) 0.0022(3) Cl16 0.0382(5) 0.0251(5) 0.0257(4) -0.0088(4) 0.0070(3) -0.0106(4) C21 0.0292(16) 0.0125(19) 0.0280(16) -0.0005(13) 0.0172(14) 0.0031(13) C22 0.0217(15) 0.021(2) 0.0269(16) -0.0027(14) 0.0128(13) -0.0061(13) C23 0.0194(15) 0.026(2) 0.0188(14) 0.0000(13) 0.0086(13) 0.0035(12) C24 0.0202(14) 0.0160(18) 0.0209(14) 0.0039(12) 0.0123(12) 0.0062(12) C25 0.0196(14) 0.0174(19) 0.0173(14) 0.0002(12) 0.0120(12) 0.0017(11) C26 0.0232(15) 0.0170(18) 0.0176(14) 0.0019(12) 0.0106(12) 0.0022(12) O21 0.0464(15) 0.0116(14) 0.0390(14) 0.0027(11) 0.0170(12) 0.0028(11) O22 0.0359(14) 0.0251(17) 0.0420(14) -0.0080(12) 0.0137(12) -0.0122(11) Cl23 0.0229(4) 0.0474(7) 0.0275(4) 0.0017(4) 0.0013(3) 0.0019(4) Cl24 0.0336(4) 0.0179(5) 0.0308(4) 0.0096(3) 0.0167(4) 0.0116(3) Cl25 0.0398(5) 0.0149(5) 0.0251(4) -0.0038(3) 0.0105(4) -0.0039(3) Cl26 0.0374(5) 0.0246(5) 0.0229(4) 0.0066(3) 0.0032(4) 0.0071(4) C31 0.0199(15) 0.019(2) 0.0351(17) 0.0039(15) 0.0120(14) 0.0037(13) C32 0.0243(15) 0.0125(18) 0.0288(16) -0.0015(13) 0.0146(14) -0.0005(13) C33 0.0242(15) 0.0120(17) 0.0221(15) -0.0018(13) 0.0098(13) -0.0024(12) C34 0.0202(14) 0.0113(17) 0.0199(14) -0.0016(11) 0.0080(12) 0.0003(11) C35 0.0201(15) 0.0159(18) 0.0190(14) -0.0059(12) 0.0075(12) -0.0051(12) C36 0.0160(14) 0.023(2) 0.0211(15) 0.0001(13) 0.0064(13) 0.0003(12) O31 0.0389(15) 0.0251(17) 0.0438(15) 0.0094(12) 0.0116(13) 0.0115(12) O32 0.0451(15) 0.0147(15) 0.0423(15) -0.0038(11) 0.0173(13) -0.0019(11) Cl33 0.0341(4) 0.0236(5) 0.0236(4) -0.0071(3) 0.0047(3) -0.0074(3) Cl34 0.0341(4) 0.0140(5) 0.0259(4) 0.0032(3) 0.0102(3) 0.0039(3) Cl35 0.0308(4) 0.0169(5) 0.0320(4) -0.0098(3) 0.0138(4) -0.0090(3) Cl36 0.0217(4) 0.0464(6) 0.0272(4) -0.0002(4) 0.0001(3) -0.0004(4) C41 0.0301(17) 0.0132(19) 0.0253(16) -0.0015(13) 0.0125(14) 0.0002(13) C42 0.0253(17) 0.022(2) 0.0258(16) -0.0037(15) 0.0105(14) -0.0050(14) C43 0.0235(17) 0.026(2) 0.0203(15) 0.0002(13) 0.0068(14) 0.0013(13) C44 0.0222(16) 0.0155(18) 0.0237(15) 0.0040(13) 0.0096(13) 0.0046(12) C45 0.0220(15) 0.0147(18) 0.0204(15) -0.0019(12) 0.0088(13) -0.0021(12) C46 0.0262(16) 0.0178(19) 0.0210(15) -0.0002(13) 0.0079(13) 0.0005(13) O41 0.0460(15) 0.0147(15) 0.0407(14) 0.0030(11) 0.0153(13) 0.0046(11) O42 0.0455(16) 0.0279(17) 0.0343(14) -0.0109(11) 0.0138(12) -0.0122(12) Cl43 0.0262(4) 0.0460(6) 0.0235(4) 0.0009(4) 0.0015(3) 0.0017(4) Cl44 0.0355(5) 0.0184(5) 0.0300(4) 0.0076(3) 0.0147(4) 0.0095(3) Cl45 0.0358(4) 0.0174(5) 0.0275(4) -0.0043(3) 0.0093(4) -0.0048(3) Cl46 0.0339(4) 0.0264(5) 0.0242(4) 0.0050(4) 0.0025(3) 0.0056(4) C51 0.0253(17) 0.023(2) 0.0313(17) 0.0041(15) 0.0149(15) 0.0018(14) C52 0.0256(16) 0.019(2) 0.0290(17) 0.0014(14) 0.0161(14) -0.0012(13) C53 0.0197(15) 0.019(2) 0.0225(16) -0.0032(13) 0.0090(13) -0.0036(12) C54 0.0230(15) 0.0140(19) 0.0261(16) 0.0011(13) 0.0118(13) 0.0010(12) C55 0.0206(15) 0.021(2) 0.0242(16) -0.0036(14) 0.0090(13) -0.0039(13) C56 0.0224(16) 0.029(2) 0.0254(17) 0.0008(14) 0.0098(14) -0.0007(14) O51 0.0373(15) 0.0309(18) 0.0465(16) 0.0131(13) 0.0107(13) 0.0140(12) O52 0.0445(15) 0.0121(15) 0.0524(16) -0.0025(12) 0.0184(13) -0.0009(11) Cl53 0.0307(4) 0.0280(5) 0.0282(4) -0.0061(4) 0.0049(4) -0.0047(4) Cl54 0.0370(5) 0.0170(5) 0.0336(4) 0.0042(3) 0.0116(4) 0.0065(3) Cl55 0.0344(5) 0.0221(5) 0.0354(4) -0.0100(4) 0.0158(4) -0.0101(4) Cl56 0.0263(4) 0.0540(7) 0.0285(4) 0.0001(4) 0.0007(4) -0.0016(4) C61 0.0325(19) 0.027(2) 0.039(2) -0.0042(17) 0.0187(17) -0.0045(16) C62 0.037(2) 0.016(2) 0.041(2) -0.0009(16) 0.0201(17) -0.0002(15) C63 0.0278(18) 0.023(2) 0.0277(18) 0.0018(15) 0.0074(15) 0.0020(14) C64 0.0347(19) 0.014(2) 0.0339(18) -0.0029(14) 0.0157(16) -0.0031(14) C65 0.0321(18) 0.022(2) 0.0269(17) 0.0055(14) 0.0119(15) 0.0070(15) C66 0.0302(19) 0.030(2) 0.0314(19) -0.0027(16) 0.0117(16) 0.0004(15) O61 0.0468(17) 0.035(2) 0.0435(15) -0.0129(13) 0.0174(14) -0.0127(13) O62 0.0495(17) 0.0187(17) 0.0519(16) -0.0008(13) 0.0178(14) 0.0016(12) Cl63 0.0362(5) 0.0298(6) 0.0339(5) 0.0056(4) 0.0073(4) 0.0043(4) Cl64 0.0425(5) 0.0202(5) 0.0391(5) -0.0043(4) 0.0148(4) -0.0056(4) Cl65 0.0417(5) 0.0242(6) 0.0397(5) 0.0090(4) 0.0213(4) 0.0117(4) Cl66 0.0308(5) 0.0553(8) 0.0324(5) 0.0004(5) 0.0081(4) 0.0023(4) C71 0.0295(18) 0.024(2) 0.0327(18) 0.0037(15) 0.0213(15) 0.0026(15) C72 0.0325(19) 0.020(2) 0.0311(18) 0.0003(15) 0.0153(16) -0.0007(15) C73 0.0300(18) 0.021(2) 0.0285(17) 0.0004(15) 0.0123(15) -0.0014(14) C74 0.0308(18) 0.018(2) 0.0223(16) -0.0002(13) 0.0092(14) -0.0011(13) C75 0.0354(19) 0.021(2) 0.0278(17) -0.0035(14) 0.0184(15) -0.0049(15) C76 0.0267(18) 0.033(3) 0.0275(18) -0.0012(15) 0.0121(15) -0.0022(15) O71 0.0397(15) 0.0309(18) 0.0456(15) 0.0125(13) 0.0177(13) 0.0122(12) O72 0.0501(16) 0.0164(16) 0.0499(16) -0.0013(12) 0.0234(14) -0.0031(12) Cl73 0.0365(5) 0.0283(6) 0.0309(4) -0.0062(4) 0.0085(4) -0.0040(4) Cl74 0.0402(5) 0.0197(5) 0.0335(4) 0.0035(4) 0.0150(4) 0.0054(4) Cl75 0.0397(5) 0.0233(6) 0.0375(5) -0.0082(4) 0.0194(4) -0.0093(4) Cl76 0.0315(5) 0.0516(7) 0.0282(4) 0.0003(4) 0.0082(4) -0.0018(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 C11 O11 1.214(4) . ? C11 C16 1.468(5) . ? C11 C12 1.548(4) . ? C12 O12 1.210(4) . ? C12 C13 1.476(4) . ? C13 C14 1.344(4) . ? C13 Cl13 1.701(3) . ? C14 C15 1.477(4) . ? C14 Cl14 1.711(3) . ? C15 C16 1.353(4) . ? C15 Cl15 1.700(3) . ? C16 Cl16 1.708(3) . ? C21 O21 1.210(4) . ? C21 C26 1.468(5) . ? C21 C22 1.546(4) . ? C22 O22 1.209(4) . ? C22 C23 1.484(5) . ? C23 C24 1.343(5) . ? C23 Cl23 1.706(3) . ? C24 C25 1.477(4) . ? C24 Cl24 1.712(3) . ? C25 C26 1.353(4) . ? C25 Cl25 1.702(3) . ? C26 Cl26 1.706(3) . ? C31 O31 1.207(4) . ? C31 C36 1.487(5) . ? C31 C32 1.551(4) . ? C32 O32 1.210(4) . ? C32 C33 1.464(4) . ? C33 C34 1.350(4) . ? C33 Cl33 1.709(3) . ? C34 C35 1.478(4) . ? C34 Cl34 1.704(3) . ? C35 C36 1.355(5) . ? C35 Cl35 1.710(3) . ? C36 Cl36 1.698(3) . ? C41 O41 1.210(4) . ? C41 C46 1.476(5) . ? C41 C42 1.544(4) . ? C42 O42 1.201(4) . ? C42 C43 1.480(5) . ? C43 C44 1.353(5) . ? C43 Cl43 1.693(3) . ? C44 C45 1.479(4) . ? C44 Cl44 1.714(3) . ? C45 C46 1.343(5) . ? C45 Cl45 1.709(3) . ? C46 Cl46 1.707(3) . ? C51 O51 1.202(4) . ? C51 C56 1.485(5) . ? C51 C52 1.548(4) . ? C52 O52 1.199(4) . ? C52 C53 1.470(5) . ? C53 C54 1.356(5) . ? C53 Cl53 1.708(3) . ? C54 C55 1.479(4) . ? C54 Cl54 1.707(3) . ? C55 C56 1.353(5) . ? C55 Cl55 1.710(4) . ? C56 Cl56 1.688(3) . ? C61 O61 1.203(4) . ? C61 C66 1.472(6) . ? C61 C62 1.553(5) . ? C62 O62 1.201(4) . ? C62 C63 1.467(5) . ? C63 C64 1.354(5) . ? C63 Cl63 1.710(3) . ? C64 C65 1.473(4) . ? C64 Cl64 1.709(4) . ? C65 C66 1.345(5) . ? C65 Cl65 1.714(4) . ? C66 Cl66 1.703(4) . ? C71 O71 1.213(4) . ? C71 C76 1.481(5) . ? C71 C72 1.556(5) . ? C72 O72 1.198(4) . ? C72 C73 1.469(5) . ? C73 C74 1.350(5) . ? C73 Cl73 1.703(3) . ? C74 C75 1.472(4) . ? C74 Cl74 1.703(4) . ? C75 C76 1.357(5) . ? C75 Cl75 1.715(4) . ? C76 Cl76 1.699(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 O11 C11 C16 123.7(3) . . ? O11 C11 C12 118.9(3) . . ? C16 C11 C12 117.4(3) . . ? O12 C12 C13 123.8(3) . . ? O12 C12 C11 118.7(3) . . ? C13 C12 C11 117.5(3) . . ? C14 C13 C12 120.5(3) . . ? C14 C13 Cl13 122.2(3) . . ? C12 C13 Cl13 117.3(2) . . ? C13 C14 C15 122.2(3) . . ? C13 C14 Cl14 121.1(2) . . ? C15 C14 Cl14 116.6(2) . . ? C16 C15 C14 121.6(3) . . ? C16 C15 Cl15 120.0(2) . . ? C14 C15 Cl15 118.4(2) . . ? C15 C16 C11 120.8(3) . . ? C15 C16 Cl16 123.2(3) . . ? C11 C16 Cl16 116.0(2) . . ? O21 C21 C26 123.7(3) . . ? O21 C21 C22 118.8(3) . . ? C26 C21 C22 117.6(3) . . ? O22 C22 C23 123.4(3) . . ? O22 C22 C21 119.2(3) . . ? C23 C22 C21 117.4(3) . . ? C24 C23 C22 120.1(3) . . ? C24 C23 Cl23 122.7(3) . . ? C22 C23 Cl23 117.2(2) . . ? C23 C24 C25 122.5(3) . . ? C23 C24 Cl24 120.5(2) . . ? C25 C24 Cl24 117.0(2) . . ? C26 C25 C24 121.7(3) . . ? C26 C25 Cl25 120.1(2) . . ? C24 C25 Cl25 118.2(2) . . ? C25 C26 C21 120.6(3) . . ? C25 C26 Cl26 123.0(3) . . ? C21 C26 Cl26 116.4(2) . . ? O31 C31 C36 123.1(3) . . ? O31 C31 C32 119.1(4) . . ? C36 C31 C32 117.7(3) . . ? O32 C32 C33 124.1(3) . . ? O32 C32 C31 118.6(3) . . ? C33 C32 C31 117.2(3) . . ? C34 C33 C32 121.1(3) . . ? C34 C33 Cl33 123.0(3) . . ? C32 C33 Cl33 115.9(2) . . ? C33 C34 C35 122.0(3) . . ? C33 C34 Cl34 120.1(2) . . ? C35 C34 Cl34 117.9(2) . . ? C36 C35 C34 122.1(3) . . ? C36 C35 Cl35 120.8(2) . . ? C34 C35 Cl35 117.0(2) . . ? C35 C36 C31 119.8(3) . . ? C35 C36 Cl36 122.5(3) . . ? C31 C36 Cl36 117.8(2) . . ? O41 C41 C46 123.4(3) . . ? O41 C41 C42 119.2(3) . . ? C46 C41 C42 117.4(3) . . ? O42 C42 C43 123.6(3) . . ? O42 C42 C41 118.8(4) . . ? C43 C42 C41 117.6(3) . . ? C44 C43 C42 120.0(3) . . ? C44 C43 Cl43 122.2(3) . . ? C42 C43 Cl43 117.8(2) . . ? C43 C44 C45 122.1(3) . . ? C43 C44 Cl44 121.0(2) . . ? C45 C44 Cl44 116.9(2) . . ? C46 C45 C44 122.1(3) . . ? C46 C45 Cl45 120.1(2) . . ? C44 C45 Cl45 117.8(2) . . ? C45 C46 C41 120.6(3) . . ? C45 C46 Cl46 123.4(3) . . ? C41 C46 Cl46 116.1(3) . . ? O51 C51 C56 123.2(3) . . ? O51 C51 C52 118.8(4) . . ? C56 C51 C52 118.1(3) . . ? O52 C52 C53 123.6(3) . . ? O52 C52 C51 119.4(3) . . ? C53 C52 C51 117.1(3) . . ? C54 C53 C52 120.9(3) . . ? C54 C53 Cl53 122.8(3) . . ? C52 C53 Cl53 116.3(3) . . ? C53 C54 C55 121.9(3) . . ? C53 C54 Cl54 120.1(2) . . ? C55 C54 Cl54 118.0(3) . . ? C56 C55 C54 122.2(3) . . ? C56 C55 Cl55 121.0(3) . . ? C54 C55 Cl55 116.8(3) . . ? C55 C56 C51 119.8(3) . . ? C55 C56 Cl56 122.3(3) . . ? C51 C56 Cl56 117.9(3) . . ? O61 C61 C66 124.4(4) . . ? O61 C61 C62 118.0(4) . . ? C66 C61 C62 117.6(3) . . ? O62 C62 C63 123.7(3) . . ? O62 C62 C61 119.4(3) . . ? C63 C62 C61 116.9(3) . . ? C64 C63 C62 121.0(3) . . ? C64 C63 Cl63 122.8(3) . . ? C62 C63 Cl63 116.2(3) . . ? C63 C64 C65 121.8(3) . . ? C63 C64 Cl64 120.0(3) . . ? C65 C64 Cl64 118.2(3) . . ? C66 C65 C64 122.0(4) . . ? C66 C65 Cl65 121.1(3) . . ? C64 C65 Cl65 116.8(3) . . ? C65 C66 C61 120.6(3) . . ? C65 C66 Cl66 122.0(3) . . ? C61 C66 Cl66 117.4(3) . . ? O71 C71 C76 123.6(3) . . ? O71 C71 C72 118.6(4) . . ? C76 C71 C72 117.8(3) . . ? O72 C72 C73 124.3(3) . . ? O72 C72 C71 118.6(3) . . ? C73 C72 C71 117.2(3) . . ? C74 C73 C72 120.8(3) . . ? C74 C73 Cl73 123.1(3) . . ? C72 C73 Cl73 116.0(3) . . ? C73 C74 C75 121.9(3) . . ? C73 C74 Cl74 120.2(3) . . ? C75 C74 Cl74 117.9(3) . . ? C76 C75 C74 122.7(3) . . ? C76 C75 Cl75 120.0(3) . . ? C74 C75 Cl75 117.3(3) . . ? C75 C76 C71 119.5(3) . . ? C75 C76 Cl76 123.0(3) . . ? C71 C76 Cl76 117.5(3) . . ? _diffrn_measured_fraction_theta_max 0.937 _diffrn_reflns_theta_full 30.00 _diffrn_measured_fraction_theta_full 0.990 _refine_diff_density_max 1.192 _refine_diff_density_min -0.502 _refine_diff_density_rms 0.154 # Attachment 'CA.cif' data_ros-ts _database_code_depnum_ccdc_archive 'CCDC 611966' _audit_creation_method SHELXL-97 _chemical_name_systematic ; tetrachloro-o-benzoquinone ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C6 Cl4 O2' _chemical_formula_sum 'C6 Cl4 O2' _chemical_formula_weight 245.86 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' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Cl Cl 0.1484 0.1585 '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 ' _symmetry_space_group_name_Hall '-P 2ybc' 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 6.0592(4) _cell_length_b 16.3472(11) _cell_length_c 8.1183(6) _cell_angle_alpha 90.00 _cell_angle_beta 94.2490(10) _cell_angle_gamma 90.00 _cell_volume 801.92(10) _cell_formula_units_Z 4 _cell_measurement_temperature 123(2) _cell_measurement_reflns_used 5251 _cell_measurement_theta_min 2.49 _cell_measurement_theta_max 31.74 _exptl_crystal_description rod _exptl_crystal_colour dark-red _exptl_crystal_size_max 0.3 _exptl_crystal_size_mid 0.2 _exptl_crystal_size_min 0.2 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 2.036 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 480 _exptl_absorpt_coefficient_mu 1.420 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min ? _exptl_absorpt_correction_T_max ? _exptl_absorpt_process_details 'Semi-empirical (SADABS procedure)' _exptl_special_details ; Tmin/Tmax ratio from multi-scan correction: 0.523 SADABS (Sheldrick, 2001) ; _diffrn_ambient_temperature 123(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 SMART' _diffrn_measurement_method ; \w-scan, frame range 0.3 deg, hemisphere ; _diffrn_detector_area_resol_mean ? _diffrn_standards_number none _diffrn_standards_interval_count 0 _diffrn_standards_interval_time 0 _diffrn_standards_decay_% 0 _diffrn_reflns_number 8492 _diffrn_reflns_av_R_equivalents 0.0307 _diffrn_reflns_av_sigmaI/netI 0.0275 _diffrn_reflns_limit_h_min -8 _diffrn_reflns_limit_h_max 8 _diffrn_reflns_limit_k_min -23 _diffrn_reflns_limit_k_max 24 _diffrn_reflns_limit_l_min -11 _diffrn_reflns_limit_l_max 11 _diffrn_reflns_theta_min 2.49 _diffrn_reflns_theta_max 31.76 _reflns_number_total 2570 _reflns_number_gt 2293 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'SMART V5.630 (BrukerAXS, 1997-2001)' _computing_cell_refinement 'SAINT V6.28 (BrukerAXS, 1997-2001)' _computing_data_reduction 'SAINT & SADABS V2.06 (Sheldrick, 2000)' _computing_structure_solution 'SHELXTL v. 6.12 (Sheldrick, 2001)' _computing_structure_refinement 'SHELXTL v. 6.12 (Sheldrick, 2001)' _computing_molecular_graphics 'XP V5.06 (BrukerAXS, 1997-99)' _computing_publication_material 'SHELXL-93, XCIF V5.05 (BrukerAXS, 1997-99)' _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. 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 _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0781P)^2^+0.0554P] 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 2570 _refine_ls_number_parameters 109 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0434 _refine_ls_R_factor_gt 0.0393 _refine_ls_wR_factor_ref 0.1057 _refine_ls_wR_factor_gt 0.1017 _refine_ls_goodness_of_fit_ref 1.056 _refine_ls_restrained_S_all 1.056 _refine_ls_shift/su_max 0.010 _refine_ls_shift/su_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_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 C1 C -0.0919(3) 0.72692(8) 0.82040(18) 0.0188(3) Uani 1 1 d . . . C2 C 0.0983(3) 0.71905(9) 0.70456(19) 0.0199(3) Uani 1 1 d . . . C3 C 0.1708(3) 0.63591(9) 0.66431(18) 0.0187(3) Uani 1 1 d . . . C4 C 0.0659(2) 0.56979(8) 0.72148(17) 0.0172(3) Uani 1 1 d . . . C5 C -0.1278(2) 0.57773(8) 0.82025(17) 0.0172(3) Uani 1 1 d . . . C6 C -0.2009(3) 0.65131(8) 0.86878(18) 0.0179(3) Uani 1 1 d . . . O1 O -0.1454(2) 0.79420(7) 0.86592(15) 0.0274(3) Uani 1 1 d . . . O2 O 0.1782(2) 0.78118(7) 0.65311(16) 0.0293(3) Uani 1 1 d . . . Cl3 Cl 0.38730(7) 0.62875(3) 0.54282(5) 0.02690(12) Uani 1 1 d . . . Cl4 Cl 0.15256(7) 0.47325(2) 0.68155(5) 0.02342(12) Uani 1 1 d . . . Cl5 Cl -0.26265(7) 0.49077(2) 0.86929(5) 0.02304(12) Uani 1 1 d . . . Cl6 Cl -0.42189(6) 0.66374(2) 0.98471(5) 0.02337(12) Uani 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 C1 0.0257(7) 0.0097(6) 0.0206(7) 0.0011(4) 0.0005(5) 0.0006(5) C2 0.0249(7) 0.0139(6) 0.0206(7) 0.0004(5) 0.0007(5) -0.0029(5) C3 0.0220(7) 0.0147(6) 0.0196(7) -0.0006(5) 0.0023(5) 0.0002(5) C4 0.0216(7) 0.0114(5) 0.0184(6) 0.0000(4) -0.0008(5) 0.0009(5) C5 0.0212(7) 0.0102(5) 0.0200(7) 0.0013(4) 0.0005(5) -0.0018(5) C6 0.0207(7) 0.0131(6) 0.0200(7) 0.0011(5) 0.0029(5) 0.0002(5) O1 0.0385(7) 0.0093(4) 0.0348(6) -0.0019(4) 0.0051(5) 0.0011(4) O2 0.0390(7) 0.0160(5) 0.0336(6) 0.0035(4) 0.0082(5) -0.0078(4) Cl3 0.0264(2) 0.0290(2) 0.0263(2) -0.00016(14) 0.00858(15) -0.00004(14) Cl4 0.0313(2) 0.01298(18) 0.0257(2) -0.00272(12) 0.00015(15) 0.00640(12) Cl5 0.0284(2) 0.01167(17) 0.0290(2) 0.00221(12) 0.00229(15) -0.00522(11) Cl6 0.0247(2) 0.01919(19) 0.0270(2) -0.00052(12) 0.00715(15) 0.00173(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 C1 O1 1.2121(17) . ? C1 C6 1.468(2) . ? C1 C2 1.546(2) . ? C2 O2 1.2126(18) . ? C2 C3 1.472(2) . ? C3 C4 1.353(2) . ? C3 Cl3 1.7026(16) . ? C4 C5 1.475(2) . ? C4 Cl4 1.7019(14) . ? C5 C6 1.351(2) . ? C5 Cl5 1.7016(14) . ? C6 Cl6 1.7049(16) . ? 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 O1 C1 C6 123.13(16) . . ? O1 C1 C2 119.29(13) . . ? C6 C1 C2 117.58(12) . . ? O2 C2 C3 124.29(16) . . ? O2 C2 C1 118.33(13) . . ? C3 C2 C1 117.38(12) . . ? C4 C3 C2 120.37(14) . . ? C4 C3 Cl3 123.05(12) . . ? C2 C3 Cl3 116.57(11) . . ? C3 C4 C5 121.93(13) . . ? C3 C4 Cl4 121.05(12) . . ? C5 C4 Cl4 117.02(10) . . ? C6 C5 C4 121.89(13) . . ? C6 C5 Cl5 120.14(12) . . ? C4 C5 Cl5 117.96(10) . . ? C5 C6 C1 120.52(15) . . ? C5 C6 Cl6 123.73(12) . . ? C1 C6 Cl6 115.75(11) . . ? _diffrn_measured_fraction_theta_max 0.946 _diffrn_reflns_theta_full 30.00 _diffrn_measured_fraction_theta_full 0.999 _refine_diff_density_max 0.938 _refine_diff_density_min -0.504 _refine_diff_density_rms 0.158 # Attachment 'DUR-CA.cif' data_ros-psx _database_code_depnum_ccdc_archive 'CCDC 611967' _audit_creation_method SHELXL-97 _chemical_name_systematic ; durene tetrachloro-o-benzoquinnone ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'c10 H14, C6 Cl4 O2' _chemical_formula_sum 'C16 H14 Cl4 O2' _chemical_formula_weight 380.07 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' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Cl Cl 0.1484 0.1585 '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 9.1022(5) _cell_length_b 13.8161(8) _cell_length_c 13.3595(8) _cell_angle_alpha 90.00 _cell_angle_beta 100.2020(10) _cell_angle_gamma 90.00 _cell_volume 1653.49(16) _cell_formula_units_Z 4 _cell_measurement_temperature 123(2) _cell_measurement_reflns_used 5137 _cell_measurement_theta_min 2.71 _cell_measurement_theta_max 31.84 _exptl_crystal_description needle _exptl_crystal_colour red _exptl_crystal_size_max 0.5 _exptl_crystal_size_mid 0.1 _exptl_crystal_size_min 0.1 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.527 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 776 _exptl_absorpt_coefficient_mu 0.718 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min ? _exptl_absorpt_correction_T_max ? _exptl_absorpt_process_details 'Semi-empirical (SADABS procedure)' _exptl_special_details ; Tmin/Tmax ratio from multi-scan correction: 0.858 SADABS (Sheldrick, 2001) ; _diffrn_ambient_temperature 123(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 'CCD area detector' _diffrn_measurement_method 'phi and omega scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number none _diffrn_standards_interval_count 0 _diffrn_standards_interval_time 0 _diffrn_standards_decay_% 0 _diffrn_reflns_number 5361 _diffrn_reflns_av_R_equivalents 0.0000 _diffrn_reflns_av_sigmaI/netI 0.0146 _diffrn_reflns_limit_h_min -13 _diffrn_reflns_limit_h_max 13 _diffrn_reflns_limit_k_min 0 _diffrn_reflns_limit_k_max 20 _diffrn_reflns_limit_l_min 0 _diffrn_reflns_limit_l_max 19 _diffrn_reflns_theta_min 2.14 _diffrn_reflns_theta_max 31.96 _reflns_number_total 5361 _reflns_number_gt 4919 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'SMART V5.630 (BrukerAXS, 1997-2001)' _computing_cell_refinement 'SAINT V6.28 (BrukerAXS, 1997-2001)' _computing_data_reduction 'SAINT & SADABS V2.06 (Sheldrick, 2000)' _computing_structure_solution 'SHELXTL v. 6.12 (Sheldrick, 2001)' _computing_structure_refinement 'SHELXTL v. 6.12 (Sheldrick, 2001)' _computing_molecular_graphics 'XP V5.06 (BrukerAXS, 1997-99)' _computing_publication_material 'SHELXL-93, XCIF V5.05 (BrukerAXS, 1997-99)' _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. 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 _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0523P)^2^+0.5673P] 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 5361 _refine_ls_number_parameters 255 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0392 _refine_ls_R_factor_gt 0.0362 _refine_ls_wR_factor_ref 0.0970 _refine_ls_wR_factor_gt 0.0947 _refine_ls_goodness_of_fit_ref 1.044 _refine_ls_restrained_S_all 1.044 _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 Cl1 Cl 0.16968(3) 0.08699(3) 0.22050(3) 0.04179(10) Uani 1 1 d . . . Cl2 Cl 0.44505(4) 0.22336(2) 0.25103(3) 0.03743(9) Uani 1 1 d . . . Cl3 Cl 0.76310(3) 0.14428(2) 0.27537(2) 0.03332(8) Uani 1 1 d . . . Cl4 Cl 0.82359(4) -0.08047(3) 0.28300(3) 0.04184(10) Uani 1 1 d . . . O1 O 0.54195(12) -0.19052(7) 0.25545(8) 0.0375(2) Uani 1 1 d . . . O2 O 0.25997(11) -0.11812(8) 0.22260(8) 0.0374(2) Uani 1 1 d . . . C1 C 0.52458(13) -0.10373(8) 0.25315(9) 0.0273(2) Uani 1 1 d . . . C2 C 0.36426(13) -0.06276(8) 0.23558(9) 0.0277(2) Uani 1 1 d . . . C3 C 0.34712(12) 0.04303(9) 0.23625(9) 0.0269(2) Uani 1 1 d . . . C4 C 0.46782(12) 0.10119(8) 0.24940(9) 0.0244(2) Uani 1 1 d . . . C5 C 0.62086(12) 0.06244(8) 0.26342(9) 0.0242(2) Uani 1 1 d . . . C6 C 0.64793(12) -0.03360(8) 0.26589(9) 0.0266(2) Uani 1 1 d . . . C1A C 0.39684(13) 0.07285(9) -0.01519(10) 0.0295(2) Uani 1 1 d . . . C2A C 0.54750(14) 0.09699(9) -0.00455(9) 0.0288(2) Uani 1 1 d . . . C3A C 0.65350(12) 0.02209(10) 0.01126(9) 0.0292(2) Uani 1 1 d . . . C4A C 0.5949(2) 0.20099(11) -0.00849(12) 0.0416(3) Uani 1 1 d . . . C5A C 0.81784(14) 0.04329(14) 0.02492(12) 0.0427(3) Uani 1 1 d . . . C1B C 0.39475(13) 0.07171(8) 0.49298(9) 0.0272(2) Uani 1 1 d . . . C2B C 0.54541(13) 0.09742(8) 0.51476(9) 0.0268(2) Uani 1 1 d . . . C3B C 0.65342(12) 0.02389(9) 0.52230(9) 0.0267(2) Uani 1 1 d . . . C4B C 0.59034(18) 0.20187(10) 0.52890(12) 0.0366(3) Uani 1 1 d . . . C5B C 0.81721(14) 0.04698(12) 0.54459(12) 0.0373(3) Uani 1 1 d . . . H1A H 0.326(2) 0.1233(15) -0.0278(14) 0.044(5) Uiso 1 1 d . . . H4AA H 0.510(3) 0.2435(18) -0.0208(17) 0.068(7) Uiso 1 1 d . . . H4AB H 0.657(2) 0.2206(15) 0.0537(16) 0.053(6) Uiso 1 1 d . . . H4AC H 0.649(2) 0.2130(15) -0.0644(15) 0.051(5) Uiso 1 1 d . . . H5AA H 0.871(3) -0.0198(19) 0.0368(18) 0.067(7) Uiso 1 1 d . . . H5AB H 0.851(2) 0.0878(15) 0.0817(16) 0.055(6) Uiso 1 1 d . . . H5AC H 0.843(2) 0.0736(15) -0.0349(15) 0.050(5) Uiso 1 1 d . . . H1B H 0.322(2) 0.1233(15) 0.4897(14) 0.043(5) Uiso 1 1 d . . . H4BA H 0.650(2) 0.2234(16) 0.4806(16) 0.057(6) Uiso 1 1 d . . . H4BB H 0.503(2) 0.2434(16) 0.5208(15) 0.054(6) Uiso 1 1 d . . . H4BC H 0.645(2) 0.2135(15) 0.5929(15) 0.049(5) Uiso 1 1 d . . . H5BA H 0.844(2) 0.0819(14) 0.6071(15) 0.047(5) Uiso 1 1 d . . . H5BB H 0.874(3) -0.0147(18) 0.5497(17) 0.059(6) Uiso 1 1 d . . . H5BC H 0.848(2) 0.0864(16) 0.4927(16) 0.055(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 Cl1 0.02220(14) 0.0462(2) 0.0565(2) 0.01132(15) 0.00573(13) 0.00815(11) Cl2 0.04186(17) 0.01740(13) 0.05242(19) 0.00200(11) 0.00667(14) 0.00586(10) Cl3 0.02739(14) 0.03024(15) 0.04230(17) -0.00308(11) 0.00608(11) -0.00972(10) Cl4 0.02737(15) 0.03892(18) 0.0583(2) 0.00096(14) 0.00520(13) 0.01321(12) O1 0.0503(6) 0.0183(4) 0.0451(5) 0.0005(3) 0.0115(4) 0.0019(4) O2 0.0343(5) 0.0357(5) 0.0413(5) 0.0021(4) 0.0039(4) -0.0144(4) C1 0.0305(5) 0.0193(5) 0.0322(5) 0.0003(4) 0.0063(4) 0.0001(4) C2 0.0274(5) 0.0234(5) 0.0321(5) 0.0018(4) 0.0050(4) -0.0039(4) C3 0.0208(4) 0.0253(5) 0.0344(6) 0.0041(4) 0.0044(4) 0.0029(4) C4 0.0249(5) 0.0170(4) 0.0315(5) 0.0022(4) 0.0053(4) 0.0020(4) C5 0.0213(4) 0.0207(5) 0.0304(5) -0.0002(4) 0.0044(4) -0.0017(3) C6 0.0225(5) 0.0223(5) 0.0347(6) 0.0000(4) 0.0045(4) 0.0036(4) C1A 0.0251(5) 0.0297(5) 0.0347(6) -0.0002(4) 0.0078(4) 0.0054(4) C2A 0.0291(5) 0.0263(5) 0.0321(6) -0.0023(4) 0.0083(4) -0.0037(4) C3A 0.0210(5) 0.0350(6) 0.0324(6) -0.0010(4) 0.0073(4) -0.0021(4) C4A 0.0549(9) 0.0281(6) 0.0426(7) -0.0037(5) 0.0109(7) -0.0115(6) C5A 0.0212(5) 0.0633(10) 0.0439(8) 0.0008(7) 0.0062(5) -0.0081(6) C1B 0.0239(5) 0.0260(5) 0.0310(5) -0.0041(4) 0.0032(4) 0.0019(4) C2B 0.0271(5) 0.0232(5) 0.0294(5) -0.0041(4) 0.0032(4) -0.0040(4) C3B 0.0217(5) 0.0288(5) 0.0291(5) -0.0033(4) 0.0027(4) -0.0037(4) C4B 0.0449(7) 0.0242(5) 0.0399(7) -0.0057(5) 0.0050(6) -0.0090(5) C5B 0.0219(5) 0.0469(8) 0.0423(7) -0.0038(6) 0.0038(5) -0.0075(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 Cl1 C3 1.7032(11) . ? Cl2 C4 1.7012(11) . ? Cl3 C5 1.7050(11) . ? Cl4 C6 1.7025(11) . ? O1 C1 1.2091(14) . ? O2 C2 1.2074(14) . ? C1 C6 1.4700(16) . ? C1 C2 1.5439(17) . ? C2 C3 1.4702(16) . ? C3 C4 1.3473(16) . ? C4 C5 1.4729(15) . ? C5 C6 1.3490(15) . ? C1A C3A 1.3934(18) 3_655 ? C1A C2A 1.3939(17) . ? C1A H1A 0.94(2) . ? C2A C3A 1.4051(17) . ? C2A C4A 1.5038(18) . ? C3A C1A 1.3934(18) 3_655 ? C3A C5A 1.5034(17) . ? C4A H4AA 0.96(3) . ? C4A H4AB 0.96(2) . ? C4A H4AC 0.98(2) . ? C5A H5AA 1.00(3) . ? C5A H5AB 0.98(2) . ? C5A H5AC 0.97(2) . ? C1B C3B 1.3953(16) 3_656 ? C1B C2B 1.3964(16) . ? C1B H1B 0.97(2) . ? C2B C3B 1.4049(16) . ? C2B C4B 1.5027(17) . ? C3B C1B 1.3953(16) 3_656 ? C3B C5B 1.5020(16) . ? C4B H4BA 0.96(2) . ? C4B H4BB 0.97(2) . ? C4B H4BC 0.92(2) . ? C5B H5BA 0.96(2) . ? C5B H5BB 0.99(2) . ? C5B H5BC 0.96(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 O1 C1 C6 123.85(11) . . ? O1 C1 C2 118.90(11) . . ? C6 C1 C2 117.25(9) . . ? O2 C2 C3 123.30(12) . . ? O2 C2 C1 119.17(11) . . ? C3 C2 C1 117.52(10) . . ? C4 C3 C2 120.58(10) . . ? C4 C3 Cl1 122.48(9) . . ? C2 C3 Cl1 116.94(9) . . ? C3 C4 C5 122.06(10) . . ? C3 C4 Cl2 119.67(9) . . ? C5 C4 Cl2 118.27(8) . . ? C6 C5 C4 121.68(10) . . ? C6 C5 Cl3 121.17(9) . . ? C4 C5 Cl3 117.14(8) . . ? C5 C6 C1 120.87(10) . . ? C5 C6 Cl4 122.72(9) . . ? C1 C6 Cl4 116.41(8) . . ? C3A C1A C2A 123.06(11) 3_655 . ? C3A C1A H1A 119.0(12) 3_655 . ? C2A C1A H1A 117.9(12) . . ? C1A C2A C3A 118.43(11) . . ? C1A C2A C4A 120.55(12) . . ? C3A C2A C4A 121.02(12) . . ? C1A C3A C2A 118.51(10) 3_655 . ? C1A C3A C5A 120.37(12) 3_655 . ? C2A C3A C5A 121.11(13) . . ? C2A C4A H4AA 111.2(14) . . ? C2A C4A H4AB 111.6(13) . . ? H4AA C4A H4AB 107.9(19) . . ? C2A C4A H4AC 112.0(12) . . ? H4AA C4A H4AC 105.5(18) . . ? H4AB C4A H4AC 108.3(17) . . ? C3A C5A H5AA 106.9(14) . . ? C3A C5A H5AB 112.4(13) . . ? H5AA C5A H5AB 110.5(19) . . ? C3A C5A H5AC 111.3(12) . . ? H5AA C5A H5AC 109.4(18) . . ? H5AB C5A H5AC 106.3(17) . . ? C3B C1B C2B 122.88(10) 3_656 . ? C3B C1B H1B 119.7(12) 3_656 . ? C2B C1B H1B 117.4(12) . . ? C1B C2B C3B 118.68(10) . . ? C1B C2B C4B 120.39(11) . . ? C3B C2B C4B 120.93(11) . . ? C1B C3B C2B 118.44(10) 3_656 . ? C1B C3B C5B 120.35(11) 3_656 . ? C2B C3B C5B 121.20(11) . . ? C2B C4B H4BA 112.7(13) . . ? C2B C4B H4BB 110.7(13) . . ? H4BA C4B H4BB 107.1(17) . . ? C2B C4B H4BC 111.9(13) . . ? H4BA C4B H4BC 107.1(18) . . ? H4BB C4B H4BC 107.1(17) . . ? C3B C5B H5BA 111.9(12) . . ? C3B C5B H5BB 108.7(13) . . ? H5BA C5B H5BB 108.7(17) . . ? C3B C5B H5BC 112.6(13) . . ? H5BA C5B H5BC 106.3(17) . . ? H5BB C5B H5BC 108.6(18) . . ? _diffrn_measured_fraction_theta_max 0.936 _diffrn_reflns_theta_full 30.00 _diffrn_measured_fraction_theta_full 0.996 _refine_diff_density_max 0.633 _refine_diff_density_min -0.331 _refine_diff_density_rms 0.066 # Attachment 'PYR-CA.cif' data_ros-rsx _database_code_depnum_ccdc_archive 'CCDC 611968' _audit_creation_method SHELXL-97 _chemical_name_systematic ; pyrene tetrachloro-o-benzoquinnone ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety '3 C16 H10, 2 C6 Cl4 O2' _chemical_formula_sum 'C60 H30 Cl8 O4' _chemical_formula_weight 1098.44 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' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Monoclinic _symmetry_space_group_name_H-M Pc _symmetry_space_group_name_Hall 'P -2yc' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' 'x, -y, z+1/2' _cell_length_a 8.3157(4) _cell_length_b 38.9670(18) _cell_length_c 14.2436(6) _cell_angle_alpha 90.00 _cell_angle_beta 91.7180(10) _cell_angle_gamma 90.00 _cell_volume 4613.4(4) _cell_formula_units_Z 4 _cell_measurement_temperature 123(2) _cell_measurement_reflns_used 7526 _cell_measurement_theta_min 2.53 _cell_measurement_theta_max 31.68 _exptl_crystal_description plate _exptl_crystal_colour brown-green _exptl_crystal_size_max 0.4 _exptl_crystal_size_mid 0.2 _exptl_crystal_size_min 0.1 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.581 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 2232 _exptl_absorpt_coefficient_mu 0.543 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min ? _exptl_absorpt_correction_T_max ? _exptl_absorpt_process_details ? _exptl_special_details ; Tmin/Tmax ratio from multi-scan correction: 0.802 SADABS (Sheldrick, 2001) ; _diffrn_ambient_temperature 123(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 'CCD area detector' _diffrn_measurement_method 'phi and omega scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number none _diffrn_standards_interval_count 0 _diffrn_standards_interval_time 0 _diffrn_standards_decay_% 0 _diffrn_reflns_number 26525 _diffrn_reflns_av_R_equivalents 0.0000 _diffrn_reflns_av_sigmaI/netI 0.0499 _diffrn_reflns_limit_h_min -12 _diffrn_reflns_limit_h_max 11 _diffrn_reflns_limit_k_min 0 _diffrn_reflns_limit_k_max 58 _diffrn_reflns_limit_l_min -20 _diffrn_reflns_limit_l_max 21 _diffrn_reflns_theta_min 1.52 _diffrn_reflns_theta_max 32.06 _reflns_number_total 26525 _reflns_number_gt 24099 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'Bruker SMART' _computing_data_reduction 'Bruker SAINT' _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. 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 _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0603P)^2^+0.7410P] 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 0.14(3) _refine_ls_number_reflns 26525 _refine_ls_number_parameters 1298 _refine_ls_number_restraints 2 _refine_ls_R_factor_all 0.0543 _refine_ls_R_factor_gt 0.0478 _refine_ls_wR_factor_ref 0.1109 _refine_ls_wR_factor_gt 0.1074 _refine_ls_goodness_of_fit_ref 1.058 _refine_ls_restrained_S_all 1.058 _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 Cl1A Cl 0.94923(7) 0.484781(18) 0.87095(5) 0.02388(13) Uani 1 1 d . . . Cl2A Cl 0.66518(8) 0.434931(16) 0.91555(5) 0.02284(13) Uani 1 1 d . . . Cl3A Cl 0.33416(7) 0.462320(16) 0.96413(5) 0.02204(12) Uani 1 1 d . . . Cl4A Cl 0.26722(8) 0.541594(18) 0.97544(5) 0.02449(13) Uani 1 1 d . . . O1A O 0.5593(3) 0.58162(5) 0.93836(15) 0.0294(5) Uani 1 1 d . . . O2A O 0.8496(2) 0.55696(6) 0.88397(16) 0.0289(5) Uani 1 1 d . . . C1AA C 0.5776(3) 0.55116(7) 0.93127(18) 0.0192(5) Uani 1 1 d . . . C2AA C 0.7445(3) 0.53705(7) 0.90261(19) 0.0200(5) Uani 1 1 d . . . C3AA C 0.7639(3) 0.49971(7) 0.89918(19) 0.0186(5) Uani 1 1 d . . . C4AA C 0.6411(3) 0.47834(6) 0.91877(17) 0.0151(4) Uani 1 1 d . . . C5AA C 0.4820(3) 0.49165(6) 0.94388(17) 0.0157(4) Uani 1 1 d . . . C6AA C 0.4520(3) 0.52555(7) 0.94889(18) 0.0179(5) Uani 1 1 d . . . C1A C 0.4693(4) 0.40245(8) 1.2070(2) 0.0306(7) Uani 1 1 d . . . H1AA H 0.4883 0.3784 1.2058 0.037 Uiso 1 1 calc R . . C2A C 0.3162(4) 0.41477(9) 1.2265(2) 0.0323(7) Uani 1 1 d . . . H2AA H 0.2313 0.3990 1.2365 0.039 Uiso 1 1 calc R . . C3A C 0.2864(3) 0.44938(9) 1.2314(2) 0.0288(6) Uani 1 1 d . . . H3AA H 0.1823 0.4572 1.2468 0.035 Uiso 1 1 calc R . . C4A C 0.4084(3) 0.47343(8) 1.21389(18) 0.0217(5) Uani 1 1 d . . . C5A C 0.3822(3) 0.50979(8) 1.2167(2) 0.0255(6) Uani 1 1 d . . . H5AA H 0.2799 0.5182 1.2338 0.031 Uiso 1 1 calc R . . C6A C 0.4975(3) 0.53213(7) 1.1959(2) 0.0241(6) Uani 1 1 d . . . H6AA H 0.4758 0.5560 1.1989 0.029 Uiso 1 1 calc R . . C7A C 0.6538(3) 0.52069(7) 1.16899(19) 0.0202(5) Uani 1 1 d . . . C8A C 0.7743(4) 0.54358(8) 1.1421(2) 0.0266(6) Uani 1 1 d . . . H8AA H 0.7538 0.5676 1.1414 0.032 Uiso 1 1 calc R . . C9A C 0.9243(4) 0.53122(8) 1.1165(2) 0.0287(6) Uani 1 1 d . . . H9AA H 1.0050 0.5470 1.0985 0.034 Uiso 1 1 calc R . . C10A C 0.9572(3) 0.49666(8) 1.11691(19) 0.0255(6) Uani 1 1 d . . . H10A H 1.0602 0.4888 1.0993 0.031 Uiso 1 1 calc R . . C11A C 0.8408(3) 0.47294(7) 1.14301(18) 0.0209(5) Uani 1 1 d . . . C12A C 0.8705(4) 0.43643(8) 1.1456(2) 0.0273(6) Uani 1 1 d . . . H12A H 0.9744 0.4281 1.1314 0.033 Uiso 1 1 calc R . . C13A C 0.7542(4) 0.41378(7) 1.1677(2) 0.0268(6) Uani 1 1 d . . . H13A H 0.7783 0.3899 1.1690 0.032 Uiso 1 1 calc R . . C14A C 0.5948(3) 0.42512(7) 1.18926(18) 0.0218(5) Uani 1 1 d . . . C15A C 0.5646(3) 0.46113(7) 1.19074(18) 0.0189(5) Uani 1 1 d . . . C16A C 0.6870(3) 0.48466(7) 1.16803(17) 0.0179(5) Uani 1 1 d . . . Cl1B Cl 0.34839(7) 0.010518(18) 0.40371(5) 0.02387(13) Uani 1 1 d . . . Cl2B Cl 0.63369(8) 0.060891(16) 0.44936(5) 0.02218(12) Uani 1 1 d . . . Cl3B Cl 0.96992(7) 0.034381(16) 0.50008(5) 0.02202(12) Uani 1 1 d . . . Cl4B Cl 1.04494(7) -0.044541(17) 0.50824(5) 0.02272(13) Uani 1 1 d . . . O1B O 0.7541(2) -0.08557(5) 0.46211(14) 0.0242(4) Uani 1 1 d . . . O2B O 0.4528(2) -0.06151(5) 0.41678(16) 0.0279(4) Uani 1 1 d . . . C1AB C 0.7312(3) -0.05498(6) 0.45992(17) 0.0178(5) Uani 1 1 d . . . C2AB C 0.5593(3) -0.04137(7) 0.43413(18) 0.0193(5) Uani 1 1 d . . . C3AB C 0.5375(3) -0.00412(7) 0.43223(18) 0.0172(5) Uani 1 1 d . . . C4AB C 0.6608(3) 0.01737(6) 0.45210(17) 0.0152(4) Uani 1 1 d . . . C5AB C 0.8237(3) 0.00452(6) 0.47732(17) 0.0164(4) Uani 1 1 d . . . C6AB C 0.8568(3) -0.02922(7) 0.48083(17) 0.0162(4) Uani 1 1 d . . . C1B C 1.0270(3) -0.05897(8) 0.27051(18) 0.0246(6) Uani 1 1 d . . . H1BA H 1.1336 -0.0523 0.2881 0.029 Uiso 1 1 calc R . . C2B C 0.9889(4) -0.09327(8) 0.26529(19) 0.0270(6) Uani 1 1 d . . . H2BA H 1.0698 -0.1100 0.2778 0.032 Uiso 1 1 calc R . . C3B C 0.8329(4) -0.10364(7) 0.24179(19) 0.0243(5) Uani 1 1 d . . . H3BA H 0.8082 -0.1274 0.2394 0.029 Uiso 1 1 calc R . . C4B C 0.7118(3) -0.07972(6) 0.22159(17) 0.0183(5) Uani 1 1 d . . . C5B C 0.5490(3) -0.08916(7) 0.19690(19) 0.0217(5) Uani 1 1 d . . . H5BA H 0.5202 -0.1128 0.1955 0.026 Uiso 1 1 calc R . . C6B C 0.4360(3) -0.06530(7) 0.17557(18) 0.0214(5) Uani 1 1 d . . . H6BA H 0.3295 -0.0726 0.1598 0.026 Uiso 1 1 calc R . . C7B C 0.4720(3) -0.02941(7) 0.17603(17) 0.0185(5) Uani 1 1 d . . . C8B C 0.3586(3) -0.00402(8) 0.15117(19) 0.0247(6) Uani 1 1 d . . . H8BA H 0.2521 -0.0106 0.1331 0.030 Uiso 1 1 calc R . . C9B C 0.3997(4) 0.03036(8) 0.1526(2) 0.0282(6) Uani 1 1 d . . . H9BA H 0.3215 0.0471 0.1346 0.034 Uiso 1 1 calc R . . C10B C 0.5539(4) 0.04087(7) 0.1800(2) 0.0242(5) Uani 1 1 d . . . H10B H 0.5794 0.0646 0.1818 0.029 Uiso 1 1 calc R . . C11B C 0.6718(3) 0.01654(7) 0.20484(18) 0.0184(5) Uani 1 1 d . . . C12B C 0.8329(3) 0.02620(7) 0.23356(19) 0.0212(5) Uani 1 1 d . . . H12B H 0.8600 0.0498 0.2379 0.025 Uiso 1 1 calc R . . C13B C 0.9463(3) 0.00239(8) 0.25448(19) 0.0218(5) Uani 1 1 d . . . H13B H 1.0518 0.0097 0.2724 0.026 Uiso 1 1 calc R . . C14B C 0.9111(3) -0.03364(7) 0.25032(17) 0.0186(5) Uani 1 1 d . . . C15B C 0.7512(3) -0.04412(6) 0.22504(17) 0.0152(4) Uani 1 1 d . . . C16B C 0.6321(3) -0.01883(6) 0.20211(16) 0.0150(4) Uani 1 1 d . . . Cl1C Cl 0.40661(7) 0.241426(18) 0.16214(5) 0.02443(13) Uani 1 1 d . . . Cl2C Cl 0.11159(8) 0.195063(16) 0.20907(5) 0.02240(12) Uani 1 1 d . . . Cl3C Cl -0.21594(7) 0.226362(17) 0.24962(5) 0.02314(13) Uani 1 1 d . . . Cl4C Cl -0.27681(8) 0.305722(18) 0.22736(5) 0.02509(13) Uani 1 1 d . . . O1C O 0.0219(2) 0.34234(5) 0.18425(16) 0.0268(4) Uani 1 1 d . . . O2C O 0.3220(2) 0.31519(5) 0.16661(15) 0.0261(4) Uani 1 1 d . . . C1AC C 0.0407(3) 0.31194(6) 0.19410(18) 0.0168(4) Uani 1 1 d . . . C2AC C 0.2096(3) 0.29599(7) 0.18045(18) 0.0194(5) Uani 1 1 d . . . C3AC C 0.2232(3) 0.25855(7) 0.18492(18) 0.0181(5) Uani 1 1 d . . . C4AC C 0.0952(3) 0.23868(6) 0.20584(18) 0.0161(5) Uani 1 1 d . . . C5AC C -0.0626(3) 0.25390(7) 0.22442(18) 0.0167(5) Uani 1 1 d . . . C6AC C -0.0902(3) 0.28787(7) 0.21719(18) 0.0174(5) Uani 1 1 d . . . C1C C -0.0541(3) 0.35502(7) 0.43955(19) 0.0230(5) Uani 1 1 d . . . H1CA H -0.1590 0.3640 0.4474 0.028 Uiso 1 1 calc R . . C2C C 0.0703(3) 0.37691(7) 0.4179(2) 0.0249(6) Uani 1 1 d . . . H2CA H 0.0498 0.4008 0.4111 0.030 Uiso 1 1 calc R . . C3C C 0.2252(3) 0.36440(7) 0.40599(19) 0.0214(5) Uani 1 1 d . . . H3CA H 0.3100 0.3799 0.3930 0.026 Uiso 1 1 calc R . . C4C C 0.2567(3) 0.32931(6) 0.41293(17) 0.0161(5) Uani 1 1 d . . . C5C C 0.4132(3) 0.31506(7) 0.39672(18) 0.0189(5) Uani 1 1 d . . . H5CA H 0.4995 0.3300 0.3830 0.023 Uiso 1 1 calc R . . C6C C 0.4403(3) 0.28094(7) 0.40056(17) 0.0182(5) Uani 1 1 d . . . H6CA H 0.5442 0.2724 0.3875 0.022 Uiso 1 1 calc R . . C7C C 0.3158(3) 0.25745(7) 0.42384(17) 0.0172(5) Uani 1 1 d . . . C8C C 0.3414(3) 0.22196(7) 0.42885(19) 0.0221(5) Uani 1 1 d . . . H8CA H 0.4446 0.2129 0.4163 0.026 Uiso 1 1 calc R . . C9C C 0.2178(3) 0.20000(7) 0.4520(2) 0.0238(5) Uani 1 1 d . . . H9CA H 0.2373 0.1760 0.4549 0.029 Uiso 1 1 calc R . . C10C C 0.0659(3) 0.21249(7) 0.47090(19) 0.0231(5) Uani 1 1 d . . . H10C H -0.0168 0.1970 0.4875 0.028 Uiso 1 1 calc R . . C11C C 0.0336(3) 0.24759(7) 0.46573(18) 0.0179(5) Uani 1 1 d . . . C12C C -0.1228(3) 0.26195(7) 0.48254(19) 0.0222(5) Uani 1 1 d . . . H12C H -0.2079 0.2471 0.4993 0.027 Uiso 1 1 calc R . . C13C C -0.1512(3) 0.29615(7) 0.4750(2) 0.0219(5) Uani 1 1 d . . . H13C H -0.2557 0.3047 0.4865 0.026 Uiso 1 1 calc R . . C14C C -0.0271(3) 0.31971(7) 0.44998(18) 0.0176(5) Uani 1 1 d . . . C15C C 0.1292(3) 0.30651(6) 0.43533(17) 0.0148(4) Uani 1 1 d . . . C16C C 0.1596(3) 0.27057(6) 0.44220(17) 0.0141(4) Uani 1 1 d . . . Cl1D Cl 0.57089(8) 0.198852(17) 0.63921(5) 0.02440(13) Uani 1 1 d . . . Cl2D Cl 0.49930(7) 0.277884(17) 0.65342(5) 0.02232(12) Uani 1 1 d . . . Cl3D Cl 0.16367(8) 0.304146(16) 0.69720(5) 0.02254(13) Uani 1 1 d . . . Cl4D Cl -0.11803(7) 0.253296(18) 0.73858(5) 0.02340(13) Uani 1 1 d . . . O1D O -0.0173(3) 0.18143(5) 0.71549(16) 0.0300(5) Uani 1 1 d . . . O2D O 0.2836(2) 0.15771(5) 0.68017(14) 0.0248(4) Uani 1 1 d . . . C1AD C 0.0908(3) 0.20186(7) 0.70650(19) 0.0193(5) Uani 1 1 d . . . C2AD C 0.2609(3) 0.18814(7) 0.68305(18) 0.0187(5) Uani 1 1 d . . . C3AD C 0.3849(3) 0.21430(7) 0.66589(18) 0.0176(5) Uani 1 1 d . . . C4AD C 0.3530(3) 0.24795(6) 0.67157(18) 0.0161(5) Uani 1 1 d . . . C5AD C 0.1922(3) 0.26083(6) 0.69506(18) 0.0163(5) Uani 1 1 d . . . C6AD C 0.0695(3) 0.23917(6) 0.71273(18) 0.0166(5) Uani 1 1 d . . . C1D C -0.1309(4) 0.23772(8) 0.9961(2) 0.0262(6) Uani 1 1 d . . . H1DA H -0.2335 0.2299 1.0143 0.031 Uiso 1 1 calc R . . C2D C -0.1001(4) 0.27269(8) 0.9928(2) 0.0284(6) Uani 1 1 d . . . H2DA H -0.1821 0.2885 1.0080 0.034 Uiso 1 1 calc R . . C3D C 0.0498(4) 0.28474(7) 0.9675(2) 0.0267(6) Uani 1 1 d . . . H3DA H 0.0689 0.3088 0.9658 0.032 Uiso 1 1 calc R . . C4D C 0.1728(3) 0.26207(7) 0.94455(19) 0.0217(5) Uani 1 1 d . . . C5D C 0.3294(4) 0.27341(7) 0.91846(19) 0.0247(6) Uani 1 1 d . . . H5DA H 0.3510 0.2973 0.9160 0.030 Uiso 1 1 calc R . . C6D C 0.4472(4) 0.25099(8) 0.8973(2) 0.0265(6) Uani 1 1 d . . . H6DA H 0.5491 0.2594 0.8797 0.032 Uiso 1 1 calc R . . C7D C 0.4200(3) 0.21444(7) 0.90110(18) 0.0218(5) Uani 1 1 d . . . C8D C 0.5403(4) 0.19032(9) 0.8817(2) 0.0307(7) Uani 1 1 d . . . H8DA H 0.6437 0.1981 0.8647 0.037 Uiso 1 1 calc R . . C9D C 0.5107(4) 0.15566(9) 0.8870(2) 0.0331(7) Uani 1 1 d . . . H9DA H 0.5944 0.1398 0.8750 0.040 Uiso 1 1 calc R . . C10D C 0.3595(4) 0.14358(8) 0.9098(2) 0.0316(7) Uani 1 1 d . . . H10D H 0.3405 0.1196 0.9123 0.038 Uiso 1 1 calc R . . C11D C 0.2351(4) 0.16647(7) 0.92898(19) 0.0235(5) Uani 1 1 d . . . C12D C 0.0769(4) 0.15527(7) 0.95235(19) 0.0259(6) Uani 1 1 d . . . H12D H 0.0543 0.1314 0.9531 0.031 Uiso 1 1 calc R . . C13D C -0.0399(4) 0.17735(8) 0.9731(2) 0.0254(6) Uani 1 1 d . . . H13D H -0.1430 0.1688 0.9883 0.030 Uiso 1 1 calc R . . C14D C -0.0121(3) 0.21373(7) 0.97282(18) 0.0215(5) Uani 1 1 d . . . C15D C 0.1422(3) 0.22601(6) 0.94735(18) 0.0177(5) Uani 1 1 d . . . C16D C 0.2657(3) 0.20244(7) 0.92520(17) 0.0190(5) Uani 1 1 d . . . C1E C 0.5199(3) 0.15188(7) 0.2819(2) 0.0215(5) Uani 1 1 d . . . H1EA H 0.4240 0.1602 0.3085 0.026 Uiso 1 1 calc R . . C2E C 0.5282(4) 0.14815(7) 0.1845(2) 0.0246(5) Uani 1 1 d . . . H2EA H 0.4381 0.1542 0.1453 0.029 Uiso 1 1 calc R . . C3E C 0.6662(3) 0.13580(7) 0.14496(19) 0.0219(5) Uani 1 1 d . . . H3EA H 0.6688 0.1329 0.0788 0.026 Uiso 1 1 calc R . . C4E C 0.8032(3) 0.12749(6) 0.20082(18) 0.0181(5) Uani 1 1 d . . . C5E C 0.9481(3) 0.11504(6) 0.16139(19) 0.0204(5) Uani 1 1 d . . . H5EA H 0.9532 0.1123 0.0953 0.024 Uiso 1 1 calc R . . C6E C 1.0776(3) 0.10713(6) 0.2162(2) 0.0201(5) Uani 1 1 d . . . H6EA H 1.1726 0.0992 0.1878 0.024 Uiso 1 1 calc R . . C7E C 1.0754(3) 0.11042(6) 0.31694(18) 0.0180(5) Uani 1 1 d . . . C8E C 1.2080(3) 0.10175(7) 0.3754(2) 0.0227(5) Uani 1 1 d . . . H8EA H 1.3031 0.0931 0.3486 0.027 Uiso 1 1 calc R . . C9E C 1.2014(3) 0.10568(7) 0.4723(2) 0.0253(6) Uani 1 1 d . . . H9EA H 1.2923 0.0999 0.5110 0.030 Uiso 1 1 calc R . . C10E C 1.0636(3) 0.11793(7) 0.51272(19) 0.0217(5) Uani 1 1 d . . . H10E H 1.0613 0.1207 0.5789 0.026 Uiso 1 1 calc R . . C11E C 0.9272(3) 0.12639(6) 0.45722(18) 0.0173(5) Uani 1 1 d . . . C12E C 0.7802(3) 0.13863(7) 0.49628(19) 0.0212(5) Uani 1 1 d . . . H12E H 0.7742 0.1412 0.5624 0.025 Uiso 1 1 calc R . . C13E C 0.6501(3) 0.14663(7) 0.44105(19) 0.0204(5) Uani 1 1 d . . . H13E H 0.5549 0.1545 0.4693 0.025 Uiso 1 1 calc R . . C14E C 0.6533(3) 0.14341(6) 0.34046(18) 0.0173(5) Uani 1 1 d . . . C15E C 0.7968(3) 0.13139(6) 0.30000(17) 0.0154(4) Uani 1 1 d . . . C16E C 0.9329(3) 0.12279(6) 0.35819(17) 0.0152(4) Uani 1 1 d . . . C1F C -0.7792(4) 0.37659(8) 0.9912(2) 0.0289(6) Uani 1 1 d . . . H1FA H -0.7755 0.3732 1.0573 0.035 Uiso 1 1 calc R . . C2F C -0.9175(4) 0.38908(8) 0.9481(3) 0.0322(7) Uani 1 1 d . . . H2FA H -1.0080 0.3941 0.9850 0.039 Uiso 1 1 calc R . . C3F C -0.9270(3) 0.39442(7) 0.8518(2) 0.0283(6) Uani 1 1 d . . . H3FA H -1.0229 0.4034 0.8235 0.034 Uiso 1 1 calc R . . C4F C -0.7962(3) 0.38662(7) 0.7962(2) 0.0220(5) Uani 1 1 d . . . C5F C -0.8007(3) 0.39063(7) 0.6956(2) 0.0256(6) Uani 1 1 d . . . H5FA H -0.8965 0.3988 0.6652 0.031 Uiso 1 1 calc R . . C6F C -0.6729(4) 0.38314(7) 0.6434(2) 0.0262(6) Uani 1 1 d . . . H6FA H -0.6799 0.3864 0.5773 0.031 Uiso 1 1 calc R . . C7F C -0.5265(3) 0.37030(7) 0.6861(2) 0.0211(5) Uani 1 1 d . . . C8F C -0.3922(4) 0.36231(7) 0.6331(2) 0.0273(6) Uani 1 1 d . . . H8FA H -0.3964 0.3657 0.5670 0.033 Uiso 1 1 calc R . . C9F C -0.2524(4) 0.34940(8) 0.6767(2) 0.0295(6) Uani 1 1 d . . . H9FA H -0.1625 0.3438 0.6400 0.035 Uiso 1 1 calc R . . C10F C -0.2435(3) 0.34463(7) 0.7730(2) 0.0266(6) Uani 1 1 d . . . H10F H -0.1476 0.3357 0.8015 0.032 Uiso 1 1 calc R . . C11F C -0.3734(3) 0.35267(6) 0.8288(2) 0.0206(5) Uani 1 1 d . . . C12F C -0.3680(3) 0.34898(7) 0.9289(2) 0.0245(6) Uani 1 1 d . . . H12F H -0.2717 0.3410 0.9592 0.029 Uiso 1 1 calc R . . C13F C -0.4951(4) 0.35642(7) 0.9810(2) 0.0247(6) Uani 1 1 d . . . H13F H -0.4868 0.3535 1.0472 0.030 Uiso 1 1 calc R . . C14F C -0.6441(3) 0.36879(7) 0.93908(19) 0.0211(5) Uani 1 1 d . . . C15F C -0.6517(3) 0.37379(6) 0.83975(19) 0.0178(5) Uani 1 1 d . . . C16F C -0.5173(3) 0.36566(6) 0.78405(19) 0.0178(5) Uani 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 Cl1A 0.0144(3) 0.0328(3) 0.0245(3) -0.0010(3) 0.0012(2) -0.0002(2) Cl2A 0.0209(3) 0.0151(3) 0.0324(3) 0.0001(2) -0.0001(2) 0.0019(2) Cl3A 0.0170(3) 0.0217(3) 0.0276(3) 0.0019(2) 0.0025(2) -0.0044(2) Cl4A 0.0226(3) 0.0260(3) 0.0250(3) -0.0007(2) 0.0025(2) 0.0072(2) O1A 0.0361(11) 0.0201(10) 0.0315(12) -0.0011(8) -0.0057(9) -0.0012(8) O2A 0.0263(10) 0.0277(11) 0.0324(12) 0.0025(8) -0.0043(9) -0.0096(8) C1AA 0.0224(12) 0.0175(12) 0.0174(12) 0.0000(9) -0.0037(10) 0.0007(9) C2AA 0.0186(11) 0.0226(13) 0.0184(12) 0.0006(9) -0.0039(9) -0.0054(9) C3AA 0.0145(11) 0.0214(12) 0.0198(12) -0.0003(9) -0.0020(9) 0.0014(9) C4AA 0.0174(11) 0.0111(10) 0.0166(11) -0.0020(8) -0.0012(9) 0.0017(8) C5AA 0.0132(10) 0.0195(11) 0.0144(11) 0.0017(9) -0.0005(8) -0.0039(8) C6AA 0.0169(11) 0.0208(12) 0.0158(12) -0.0013(9) -0.0015(9) 0.0021(9) C1A 0.0472(18) 0.0265(15) 0.0178(13) 0.0016(11) -0.0059(13) -0.0108(13) C2A 0.0353(16) 0.0456(19) 0.0157(13) 0.0023(12) -0.0025(11) -0.0161(14) C3A 0.0212(13) 0.0482(19) 0.0168(13) 0.0021(12) -0.0016(10) -0.0075(12) C4A 0.0200(12) 0.0343(15) 0.0105(11) 0.0005(10) -0.0027(9) 0.0000(10) C5A 0.0185(12) 0.0383(16) 0.0196(13) -0.0012(11) -0.0030(10) 0.0103(11) C6A 0.0285(14) 0.0235(13) 0.0198(13) -0.0025(10) -0.0054(11) 0.0100(11) C7A 0.0228(12) 0.0218(13) 0.0158(12) 0.0012(9) -0.0012(9) 0.0019(10) C8A 0.0360(15) 0.0229(14) 0.0209(13) 0.0017(10) -0.0019(12) -0.0030(11) C9A 0.0308(15) 0.0380(17) 0.0171(13) 0.0002(11) -0.0005(11) -0.0117(12) C10A 0.0190(12) 0.0408(17) 0.0168(13) -0.0036(11) 0.0013(10) -0.0008(11) C11A 0.0195(12) 0.0285(14) 0.0146(12) -0.0040(10) -0.0008(9) -0.0005(10) C12A 0.0252(13) 0.0340(16) 0.0226(14) -0.0092(11) -0.0037(11) 0.0108(11) C13A 0.0375(16) 0.0188(13) 0.0235(14) -0.0046(10) -0.0075(12) 0.0069(11) C14A 0.0313(14) 0.0204(13) 0.0134(12) -0.0023(9) -0.0041(10) -0.0032(10) C15A 0.0199(12) 0.0234(13) 0.0134(11) -0.0004(9) -0.0031(9) 0.0002(9) C16A 0.0200(11) 0.0212(12) 0.0122(11) -0.0015(9) -0.0024(9) 0.0010(9) Cl1B 0.0175(3) 0.0297(3) 0.0243(3) 0.0014(2) -0.0019(2) -0.0015(2) Cl2B 0.0225(3) 0.0141(3) 0.0300(3) -0.0002(2) 0.0022(2) -0.0012(2) Cl3B 0.0185(3) 0.0200(3) 0.0275(3) -0.0022(2) -0.0011(2) -0.0069(2) Cl4B 0.0205(3) 0.0243(3) 0.0232(3) 0.0023(2) -0.0016(2) 0.0018(2) O1B 0.0317(10) 0.0180(9) 0.0228(10) 0.0005(7) -0.0008(8) -0.0030(8) O2B 0.0259(10) 0.0247(10) 0.0331(11) -0.0027(8) -0.0015(9) -0.0093(8) C1AB 0.0243(12) 0.0189(12) 0.0103(11) 0.0013(8) 0.0026(9) -0.0017(9) C2AB 0.0212(12) 0.0189(12) 0.0177(12) 0.0010(9) 0.0015(10) -0.0050(9) C3AB 0.0156(10) 0.0192(12) 0.0167(12) 0.0010(9) -0.0006(9) -0.0007(9) C4AB 0.0176(11) 0.0136(11) 0.0144(11) 0.0014(8) 0.0028(8) -0.0027(8) C5AB 0.0160(10) 0.0197(11) 0.0135(11) -0.0004(8) 0.0017(8) -0.0057(9) C6AB 0.0149(10) 0.0209(12) 0.0129(11) -0.0002(8) 0.0005(8) 0.0000(9) C1B 0.0207(12) 0.0407(16) 0.0124(12) 0.0020(10) 0.0008(10) 0.0062(11) C2B 0.0317(14) 0.0342(16) 0.0153(12) 0.0016(10) 0.0037(11) 0.0154(12) C3B 0.0354(14) 0.0212(13) 0.0165(12) -0.0005(10) 0.0053(11) 0.0072(11) C4B 0.0265(12) 0.0171(11) 0.0117(11) -0.0009(8) 0.0053(9) 0.0002(9) C5B 0.0305(14) 0.0174(12) 0.0174(12) -0.0060(9) 0.0060(10) -0.0053(10) C6B 0.0192(12) 0.0289(14) 0.0161(12) -0.0054(10) 0.0027(9) -0.0056(10) C7B 0.0178(11) 0.0272(13) 0.0105(11) -0.0020(9) 0.0017(8) -0.0007(9) C8B 0.0182(12) 0.0390(16) 0.0168(12) -0.0046(11) -0.0011(10) 0.0047(11) C9B 0.0302(14) 0.0327(15) 0.0215(14) 0.0014(11) -0.0033(11) 0.0146(12) C10B 0.0336(15) 0.0184(12) 0.0205(13) 0.0028(10) 0.0009(11) 0.0029(11) C11B 0.0224(12) 0.0183(12) 0.0147(11) 0.0004(9) 0.0031(9) -0.0007(9) C12B 0.0261(13) 0.0202(12) 0.0176(12) 0.0012(9) 0.0034(10) -0.0061(10) C13B 0.0180(11) 0.0313(14) 0.0162(12) -0.0013(10) 0.0018(9) -0.0071(10) C14B 0.0148(11) 0.0297(13) 0.0113(11) -0.0004(9) 0.0025(8) 0.0003(9) C15B 0.0164(11) 0.0167(11) 0.0126(10) 0.0006(8) 0.0013(8) -0.0010(8) C16B 0.0166(11) 0.0191(12) 0.0093(10) 0.0018(8) 0.0006(8) -0.0007(9) Cl1C 0.0142(3) 0.0314(3) 0.0277(3) -0.0001(3) 0.0013(2) 0.0043(2) Cl2C 0.0225(3) 0.0181(3) 0.0264(3) 0.0017(2) -0.0023(2) 0.0022(2) Cl3C 0.0161(3) 0.0227(3) 0.0307(3) 0.0033(2) 0.0013(2) -0.0040(2) Cl4C 0.0173(3) 0.0266(3) 0.0316(3) 0.0016(3) 0.0049(2) 0.0055(2) O1C 0.0286(10) 0.0190(9) 0.0332(11) 0.0007(8) 0.0042(8) 0.0009(8) O2C 0.0194(9) 0.0283(10) 0.0306(11) 0.0029(8) 0.0013(8) -0.0071(8) C1AC 0.0164(11) 0.0191(11) 0.0152(11) -0.0013(9) 0.0022(9) 0.0014(9) C2AC 0.0149(11) 0.0265(13) 0.0166(12) 0.0001(10) -0.0007(9) -0.0008(9) C3AC 0.0146(10) 0.0231(12) 0.0164(11) 0.0012(9) -0.0017(9) 0.0026(9) C4AC 0.0170(11) 0.0128(11) 0.0185(11) 0.0010(8) -0.0028(9) 0.0011(8) C5AC 0.0118(10) 0.0213(12) 0.0170(12) 0.0014(9) -0.0012(9) -0.0040(9) C6AC 0.0127(10) 0.0223(12) 0.0174(12) -0.0015(9) 0.0017(9) 0.0026(9) C1C 0.0195(12) 0.0256(13) 0.0236(13) -0.0028(10) -0.0017(10) 0.0059(10) C2C 0.0305(14) 0.0175(12) 0.0264(14) 0.0016(10) -0.0028(11) 0.0036(10) C3C 0.0239(12) 0.0202(12) 0.0198(12) 0.0035(9) -0.0017(10) -0.0034(10) C4C 0.0153(11) 0.0193(11) 0.0136(11) 0.0019(8) -0.0021(9) -0.0008(8) C5C 0.0141(11) 0.0256(13) 0.0170(11) 0.0029(9) 0.0018(9) -0.0021(9) C6C 0.0142(10) 0.0275(13) 0.0132(11) 0.0003(9) 0.0032(8) 0.0019(9) C7C 0.0168(11) 0.0215(12) 0.0131(11) -0.0002(9) -0.0017(9) 0.0017(9) C8C 0.0257(13) 0.0199(12) 0.0205(12) -0.0009(10) -0.0017(10) 0.0051(10) C9C 0.0304(14) 0.0177(12) 0.0232(13) -0.0002(10) -0.0009(11) -0.0002(10) C10C 0.0306(14) 0.0181(12) 0.0204(13) 0.0007(9) -0.0019(11) -0.0091(10) C11C 0.0183(11) 0.0202(12) 0.0149(11) 0.0001(9) -0.0009(9) -0.0033(9) C12C 0.0162(11) 0.0293(14) 0.0211(13) -0.0006(10) 0.0008(10) -0.0098(10) C13C 0.0129(11) 0.0291(14) 0.0238(13) -0.0043(11) 0.0026(9) 0.0001(10) C14C 0.0156(11) 0.0207(12) 0.0164(11) -0.0018(9) 0.0013(9) 0.0006(9) C15C 0.0130(10) 0.0171(11) 0.0141(11) 0.0003(8) -0.0009(8) -0.0008(8) C16C 0.0147(10) 0.0153(11) 0.0122(10) -0.0001(8) 0.0002(8) -0.0019(8) Cl1D 0.0199(3) 0.0259(3) 0.0275(3) -0.0056(3) 0.0027(2) 0.0045(2) Cl2D 0.0183(3) 0.0211(3) 0.0277(3) 0.0004(2) 0.0034(2) -0.0055(2) Cl3D 0.0223(3) 0.0136(3) 0.0316(3) 0.0002(2) -0.0006(2) 0.0009(2) Cl4D 0.0151(3) 0.0278(3) 0.0273(3) -0.0002(3) 0.0016(2) 0.0006(2) O1D 0.0268(10) 0.0222(10) 0.0412(13) 0.0020(9) 0.0026(9) -0.0091(8) O2D 0.0309(10) 0.0158(9) 0.0275(10) -0.0012(7) -0.0034(8) -0.0009(8) C1AD 0.0213(12) 0.0176(12) 0.0187(12) 0.0005(9) -0.0033(10) -0.0017(9) C2AD 0.0218(12) 0.0183(12) 0.0158(11) -0.0018(9) -0.0020(9) -0.0014(9) C3AD 0.0164(11) 0.0202(12) 0.0162(11) -0.0033(9) 0.0006(9) 0.0006(9) C4AD 0.0180(11) 0.0161(11) 0.0142(11) -0.0023(8) 0.0001(9) -0.0045(9) C5AD 0.0169(11) 0.0161(11) 0.0157(11) -0.0017(9) -0.0033(9) 0.0003(9) C6AD 0.0158(11) 0.0191(12) 0.0150(11) 0.0010(9) 0.0009(9) -0.0019(9) C1D 0.0257(13) 0.0360(16) 0.0168(13) -0.0026(11) -0.0013(10) 0.0071(12) C2D 0.0356(16) 0.0332(16) 0.0162(13) -0.0033(11) -0.0039(11) 0.0158(12) C3D 0.0418(16) 0.0185(13) 0.0192(13) -0.0010(10) -0.0087(12) 0.0067(11) C4D 0.0333(14) 0.0167(12) 0.0145(11) -0.0002(9) -0.0083(10) 0.0013(10) C5D 0.0336(15) 0.0228(13) 0.0172(12) 0.0006(10) -0.0075(11) -0.0085(11) C6D 0.0275(14) 0.0326(15) 0.0191(13) 0.0014(11) -0.0043(11) -0.0099(12) C7D 0.0242(13) 0.0274(14) 0.0137(11) -0.0008(10) -0.0031(10) 0.0029(10) C8D 0.0225(13) 0.050(2) 0.0191(13) -0.0064(13) -0.0020(11) 0.0112(13) C9D 0.0397(17) 0.0385(17) 0.0208(14) -0.0053(12) -0.0049(12) 0.0227(14) C10D 0.0522(19) 0.0257(14) 0.0165(13) -0.0015(10) -0.0054(13) 0.0153(13) C11D 0.0395(15) 0.0152(12) 0.0157(12) 0.0002(9) -0.0010(11) 0.0027(11) C12D 0.0455(17) 0.0153(12) 0.0169(12) 0.0011(9) -0.0004(12) -0.0053(11) C13D 0.0291(14) 0.0292(14) 0.0179(13) 0.0021(10) 0.0004(11) -0.0071(11) C14D 0.0230(12) 0.0279(14) 0.0137(12) -0.0008(10) -0.0017(10) 0.0009(10) C15D 0.0229(12) 0.0166(11) 0.0133(11) -0.0001(9) -0.0024(9) -0.0004(9) C16D 0.0262(13) 0.0183(12) 0.0122(11) -0.0007(9) -0.0026(9) 0.0027(9) C1E 0.0181(11) 0.0171(12) 0.0296(14) 0.0008(10) 0.0032(10) 0.0019(9) C2E 0.0274(13) 0.0204(13) 0.0256(14) 0.0006(10) -0.0040(11) 0.0022(10) C3E 0.0294(14) 0.0170(12) 0.0191(12) 0.0019(9) -0.0013(10) -0.0021(10) C4E 0.0240(12) 0.0139(11) 0.0164(12) 0.0007(8) 0.0012(9) -0.0021(9) C5E 0.0299(13) 0.0138(11) 0.0179(12) -0.0011(9) 0.0077(10) -0.0023(9) C6E 0.0236(12) 0.0118(11) 0.0255(13) -0.0014(9) 0.0120(10) -0.0012(9) C7E 0.0203(11) 0.0133(11) 0.0204(12) 0.0023(9) 0.0030(9) -0.0011(9) C8E 0.0189(12) 0.0196(12) 0.0298(14) 0.0071(10) 0.0024(10) -0.0002(9) C9E 0.0225(13) 0.0258(14) 0.0273(14) 0.0062(11) -0.0060(11) -0.0054(10) C10E 0.0273(13) 0.0178(12) 0.0197(12) 0.0032(9) -0.0020(10) -0.0060(10) C11E 0.0220(11) 0.0119(10) 0.0181(11) 0.0006(9) 0.0020(9) -0.0034(9) C12E 0.0297(13) 0.0188(12) 0.0153(12) -0.0019(9) 0.0062(10) -0.0022(10) C13E 0.0221(12) 0.0177(12) 0.0220(13) -0.0040(9) 0.0079(10) 0.0010(9) C14E 0.0195(11) 0.0138(11) 0.0188(12) -0.0005(9) 0.0045(9) -0.0015(9) C15E 0.0186(11) 0.0095(10) 0.0183(11) -0.0015(8) 0.0028(9) -0.0022(8) C16E 0.0196(11) 0.0101(10) 0.0162(11) 0.0003(8) 0.0040(9) -0.0023(8) C1F 0.0317(15) 0.0301(15) 0.0255(14) -0.0091(11) 0.0101(12) -0.0126(12) C2F 0.0260(14) 0.0260(15) 0.0453(19) -0.0158(13) 0.0122(13) -0.0078(11) C3F 0.0183(12) 0.0231(14) 0.0435(18) -0.0099(12) 0.0008(12) -0.0023(10) C4F 0.0213(12) 0.0135(11) 0.0309(14) -0.0040(10) -0.0049(10) 0.0006(9) C5F 0.0240(13) 0.0181(12) 0.0338(15) 0.0006(11) -0.0113(12) 0.0008(10) C6F 0.0382(15) 0.0188(13) 0.0209(13) 0.0020(10) -0.0093(12) -0.0014(11) C7F 0.0284(13) 0.0130(11) 0.0218(13) -0.0002(9) -0.0001(10) -0.0043(9) C8F 0.0342(15) 0.0226(13) 0.0256(14) -0.0041(11) 0.0075(12) -0.0072(11) C9F 0.0270(14) 0.0250(14) 0.0370(17) -0.0089(12) 0.0120(12) -0.0037(11) C10F 0.0207(12) 0.0173(12) 0.0418(17) -0.0067(11) 0.0020(12) -0.0010(10) C11F 0.0190(12) 0.0135(11) 0.0292(14) -0.0025(10) -0.0019(10) -0.0003(9) C12F 0.0240(13) 0.0206(13) 0.0283(15) 0.0000(10) -0.0084(11) 0.0004(10) C13F 0.0353(15) 0.0200(13) 0.0185(13) 0.0009(10) -0.0028(11) -0.0063(11) C14F 0.0258(13) 0.0147(11) 0.0228(13) -0.0030(9) 0.0021(10) -0.0066(9) C15F 0.0191(11) 0.0119(11) 0.0222(12) -0.0036(9) -0.0007(9) -0.0020(8) C16F 0.0187(11) 0.0105(10) 0.0240(13) -0.0026(9) -0.0009(9) -0.0011(8) _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 Cl1A C3AA 1.706(3) . ? Cl2A C4AA 1.704(2) . ? Cl3A C5AA 1.709(2) . ? Cl4A C6AA 1.711(3) . ? O1A C1AA 1.201(3) . ? O2A C2AA 1.204(3) . ? C1AA C6AA 1.472(4) . ? C1AA C2AA 1.558(4) . ? C2AA C3AA 1.465(4) . ? C3AA C4AA 1.353(4) . ? C4AA C5AA 1.475(3) . ? C5AA C6AA 1.347(4) . ? C1A C14A 1.396(4) . ? C1A C2A 1.397(5) . ? C1A H1AA 0.9500 . ? C2A C3A 1.373(5) . ? C2A H2AA 0.9500 . ? C3A C4A 1.409(4) . ? C3A H3AA 0.9500 . ? C4A C15A 1.433(4) . ? C4A C5A 1.434(4) . ? C5A C6A 1.335(4) . ? C5A H5AA 0.9500 . ? C6A C7A 1.437(4) . ? C6A H6AA 0.9500 . ? C7A C8A 1.403(4) . ? C7A C16A 1.431(4) . ? C8A C9A 1.396(5) . ? C8A H8AA 0.9500 . ? C9A C10A 1.374(5) . ? C9A H9AA 0.9500 . ? C10A C11A 1.397(4) . ? C10A H10A 0.9500 . ? C11A C16A 1.414(4) . ? C11A C12A 1.444(4) . ? C12A C13A 1.353(5) . ? C12A H12A 0.9500 . ? C13A C14A 1.440(4) . ? C13A H13A 0.9500 . ? C14A C15A 1.426(4) . ? C15A C16A 1.415(4) . ? Cl1B C3AB 1.710(3) . ? Cl2B C4AB 1.711(2) . ? Cl3B C5AB 1.707(2) . ? Cl4B C6AB 1.709(2) . ? O1B C1AB 1.207(3) . ? O2B C2AB 1.204(3) . ? C1AB C6AB 1.472(3) . ? C1AB C2AB 1.559(4) . ? C2AB C3AB 1.463(4) . ? C3AB C4AB 1.348(3) . ? C4AB C5AB 1.478(3) . ? C5AB C6AB 1.344(4) . ? C1B C2B 1.375(5) . ? C1B C14B 1.403(4) . ? C1B H1BA 0.9500 . ? C2B C3B 1.390(4) . ? C2B H2BA 0.9500 . ? C3B C4B 1.395(4) . ? C3B H3BA 0.9500 . ? C4B C15B 1.425(3) . ? C4B C5B 1.437(4) . ? C5B C6B 1.350(4) . ? C5B H5BA 0.9500 . ? C6B C7B 1.430(4) . ? C6B H6BA 0.9500 . ? C7B C8B 1.405(4) . ? C7B C16B 1.432(3) . ? C8B C9B 1.382(5) . ? C8B H8BA 0.9500 . ? C9B C10B 1.390(4) . ? C9B H9BA 0.9500 . ? C10B C11B 1.402(4) . ? C10B H10B 0.9500 . ? C11B C16B 1.417(3) . ? C11B C12B 1.439(4) . ? C12B C13B 1.350(4) . ? C12B H12B 0.9500 . ? C13B C14B 1.435(4) . ? C13B H13B 0.9500 . ? C14B C15B 1.427(3) . ? C15B C16B 1.428(3) . ? Cl1C C3AC 1.705(3) . ? Cl2C C4AC 1.705(2) . ? Cl3C C5AC 1.713(2) . ? Cl4C C6AC 1.710(2) . ? O1C C1AC 1.202(3) . ? O2C C2AC 1.218(3) . ? C1AC C6AC 1.481(4) . ? C1AC C2AC 1.553(4) . ? C2AC C3AC 1.465(4) . ? C3AC C4AC 1.357(4) . ? C4AC C5AC 1.471(3) . ? C5AC C6AC 1.347(4) . ? C1C C2C 1.382(4) . ? C1C C14C 1.401(4) . ? C1C H1CA 0.9500 . ? C2C C3C 1.393(4) . ? C2C H2CA 0.9500 . ? C3C C4C 1.395(4) . ? C3C H3CA 0.9500 . ? C4C C15C 1.427(3) . ? C4C C5C 1.440(3) . ? C5C C6C 1.350(4) . ? C5C H5CA 0.9500 . ? C6C C7C 1.429(4) . ? C6C H6CA 0.9500 . ? C7C C8C 1.401(4) . ? C7C C16C 1.427(3) . ? C8C C9C 1.385(4) . ? C8C H8CA 0.9500 . ? C9C C10C 1.388(4) . ? C9C H9CA 0.9500 . ? C10C C11C 1.395(4) . ? C10C H10C 0.9500 . ? C11C C16C 1.426(3) . ? C11C C12C 1.442(4) . ? C12C C13C 1.357(4) . ? C12C H12C 0.9500 . ? C13C C14C 1.434(4) . ? C13C H13C 0.9500 . ? C14C C15C 1.419(3) . ? C15C C16C 1.426(3) . ? Cl1D C3AD 1.713(3) . ? Cl2D C4AD 1.710(3) . ? Cl3D C5AD 1.705(3) . ? Cl4D C6AD 1.704(3) . ? O1D C1AD 1.211(3) . ? O2D C2AD 1.202(3) . ? C1AD C6AD 1.468(4) . ? C1AD C2AD 1.558(4) . ? C2AD C3AD 1.475(4) . ? C3AD C4AD 1.341(4) . ? C4AD C5AD 1.477(4) . ? C5AD C6AD 1.353(3) . ? C1D C2D 1.388(5) . ? C1D C14D 1.407(4) . ? C1D H1DA 0.9500 . ? C2D C3D 1.389(5) . ? C2D H2DA 0.9500 . ? C3D C4D 1.398(4) . ? C3D H3DA 0.9500 . ? C4D C15D 1.429(4) . ? C4D C5D 1.434(4) . ? C5D C6D 1.353(4) . ? C5D H5DA 0.9500 . ? C6D C7D 1.443(4) . ? C6D H6DA 0.9500 . ? C7D C8D 1.406(4) . ? C7D C16D 1.418(4) . ? C8D C9D 1.376(5) . ? C8D H8DA 0.9500 . ? C9D C10D 1.390(5) . ? C9D H9DA 0.9500 . ? C10D C11D 1.399(4) . ? C10D H10D 0.9500 . ? C11D C16D 1.426(4) . ? C11D C12D 1.435(4) . ? C12D C13D 1.337(4) . ? C12D H12D 0.9500 . ? C13D C14D 1.436(4) . ? C13D H13D 0.9500 . ? C14D C15D 1.426(4) . ? C15D C16D 1.420(4) . ? C1E C2E 1.398(4) . ? C1E C14E 1.407(4) . ? C1E H1EA 0.9500 . ? C2E C3E 1.380(4) . ? C2E H2EA 0.9500 . ? C3E C4E 1.408(4) . ? C3E H3EA 0.9500 . ? C4E C15E 1.423(4) . ? C4E C5E 1.429(4) . ? C5E C6E 1.346(4) . ? C5E H5EA 0.9500 . ? C6E C7E 1.442(4) . ? C6E H6EA 0.9500 . ? C7E C8E 1.403(4) . ? C7E C16E 1.422(3) . ? C8E C9E 1.391(4) . ? C8E H8EA 0.9500 . ? C9E C10E 1.382(4) . ? C9E H9EA 0.9500 . ? C10E C11E 1.402(4) . ? C10E H10E 0.9500 . ? C11E C16E 1.420(4) . ? C11E C12E 1.440(4) . ? C12E C13E 1.354(4) . ? C12E H12E 0.9500 . ? C13E C14E 1.439(4) . ? C13E H13E 0.9500 . ? C14E C15E 1.420(3) . ? C15E C16E 1.423(3) . ? C1F C2F 1.376(5) . ? C1F C14F 1.399(4) . ? C1F H1FA 0.9500 . ? C2F C3F 1.388(5) . ? C2F H2FA 0.9500 . ? C3F C4F 1.398(4) . ? C3F H3FA 0.9500 . ? C4F C15F 1.426(4) . ? C4F C5F 1.440(4) . ? C5F C6F 1.347(5) . ? C5F H5FA 0.9500 . ? C6F C7F 1.434(4) . ? C6F H6FA 0.9500 . ? C7F C8F 1.402(4) . ? C7F C16F 1.407(4) . ? C8F C9F 1.396(5) . ? C8F H8FA 0.9500 . ? C9F C10F 1.384(5) . ? C9F H9FA 0.9500 . ? C10F C11F 1.395(4) . ? C10F H10F 0.9500 . ? C11F C16F 1.431(3) . ? C11F C12F 1.433(4) . ? C12F C13F 1.342(4) . ? C12F H12F 0.9500 . ? C13F C14F 1.442(4) . ? C13F H13F 0.9500 . ? C14F C15F 1.428(4) . ? C15F C16F 1.425(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 O1A C1AA C6AA 124.3(3) . . ? O1A C1AA C2AA 119.1(2) . . ? C6AA C1AA C2AA 116.6(2) . . ? O2A C2AA C3AA 123.4(3) . . ? O2A C2AA C1AA 119.2(2) . . ? C3AA C2AA C1AA 117.3(2) . . ? C4AA C3AA C2AA 121.3(2) . . ? C4AA C3AA Cl1A 122.1(2) . . ? C2AA C3AA Cl1A 116.59(19) . . ? C3AA C4AA C5AA 121.4(2) . . ? C3AA C4AA Cl2A 121.01(19) . . ? C5AA C4AA Cl2A 117.54(18) . . ? C6AA C5AA C4AA 121.8(2) . . ? C6AA C5AA Cl3A 120.8(2) . . ? C4AA C5AA Cl3A 117.43(18) . . ? C5AA C6AA C1AA 121.5(2) . . ? C5AA C6AA Cl4A 122.6(2) . . ? C1AA C6AA Cl4A 115.90(19) . . ? C14A C1A C2A 120.6(3) . . ? C14A C1A H1AA 119.7 . . ? C2A C1A H1AA 119.7 . . ? C3A C2A C1A 121.0(3) . . ? C3A C2A H2AA 119.5 . . ? C1A C2A H2AA 119.5 . . ? C2A C3A C4A 120.8(3) . . ? C2A C3A H3AA 119.6 . . ? C4A C3A H3AA 119.6 . . ? C3A C4A C15A 118.7(3) . . ? C3A C4A C5A 122.8(3) . . ? C15A C4A C5A 118.5(3) . . ? C6A C5A C4A 121.8(3) . . ? C6A C5A H5AA 119.1 . . ? C4A C5A H5AA 119.1 . . ? C5A C6A C7A 121.2(3) . . ? C5A C6A H6AA 119.4 . . ? C7A C6A H6AA 119.4 . . ? C8A C7A C16A 118.8(3) . . ? C8A C7A C6A 122.3(3) . . ? C16A C7A C6A 118.9(3) . . ? C9A C8A C7A 120.2(3) . . ? C9A C8A H8AA 119.9 . . ? C7A C8A H8AA 119.9 . . ? C10A C9A C8A 121.1(3) . . ? C10A C9A H9AA 119.4 . . ? C8A C9A H9AA 119.4 . . ? C9A C10A C11A 120.7(3) . . ? C9A C10A H10A 119.7 . . ? C11A C10A H10A 119.7 . . ? C10A C11A C16A 119.5(3) . . ? C10A C11A C12A 122.6(3) . . ? C16A C11A C12A 117.8(3) . . ? C13A C12A C11A 121.7(3) . . ? C13A C12A H12A 119.1 . . ? C11A C12A H12A 119.1 . . ? C12A C13A C14A 121.2(3) . . ? C12A C13A H13A 119.4 . . ? C14A C13A H13A 119.4 . . ? C1A C14A C15A 119.2(3) . . ? C1A C14A C13A 122.9(3) . . ? C15A C14A C13A 118.0(3) . . ? C16A C15A C14A 120.4(2) . . ? C16A C15A C4A 120.0(2) . . ? C14A C15A C4A 119.6(3) . . ? C11A C16A C15A 120.7(2) . . ? C11A C16A C7A 119.7(2) . . ? C15A C16A C7A 119.6(2) . . ? O1B C1AB C6AB 123.9(2) . . ? O1B C1AB C2AB 119.0(2) . . ? C6AB C1AB C2AB 117.1(2) . . ? O2B C2AB C3AB 123.6(2) . . ? O2B C2AB C1AB 119.4(2) . . ? C3AB C2AB C1AB 117.0(2) . . ? C4AB C3AB C2AB 121.3(2) . . ? C4AB C3AB Cl1B 122.1(2) . . ? C2AB C3AB Cl1B 116.61(18) . . ? C3AB C4AB C5AB 121.8(2) . . ? C3AB C4AB Cl2B 120.80(19) . . ? C5AB C4AB Cl2B 117.43(17) . . ? C6AB C5AB C4AB 121.7(2) . . ? C6AB C5AB Cl3B 121.05(19) . . ? C4AB C5AB Cl3B 117.23(18) . . ? C5AB C6AB C1AB 121.1(2) . . ? C5AB C6AB Cl4B 122.38(19) . . ? C1AB C6AB Cl4B 116.54(19) . . ? C2B C1B C14B 121.1(3) . . ? C2B C1B H1BA 119.5 . . ? C14B C1B H1BA 119.5 . . ? C1B C2B C3B 120.5(3) . . ? C1B C2B H2BA 119.7 . . ? C3B C2B H2BA 119.8 . . ? C2B C3B C4B 121.2(3) . . ? C2B C3B H3BA 119.4 . . ? C4B C3B H3BA 119.4 . . ? C3B C4B C15B 118.6(2) . . ? C3B C4B C5B 123.2(2) . . ? C15B C4B C5B 118.1(2) . . ? C6B C5B C4B 121.6(2) . . ? C6B C5B H5BA 119.2 . . ? C4B C5B H5BA 119.2 . . ? C5B C6B C7B 121.9(2) . . ? C5B C6B H6BA 119.1 . . ? C7B C6B H6BA 119.1 . . ? C8B C7B C6B 123.3(2) . . ? C8B C7B C16B 118.3(2) . . ? C6B C7B C16B 118.4(2) . . ? C9B C8B C7B 121.0(3) . . ? C9B C8B H8BA 119.5 . . ? C7B C8B H8BA 119.5 . . ? C8B C9B C10B 121.0(3) . . ? C8B C9B H9BA 119.5 . . ? C10B C9B H9BA 119.5 . . ? C9B C10B C11B 120.2(3) . . ? C9B C10B H10B 119.9 . . ? C11B C10B H10B 119.9 . . ? C10B C11B C16B 119.3(2) . . ? C10B C11B C12B 122.2(2) . . ? C16B C11B C12B 118.4(2) . . ? C13B C12B C11B 121.4(2) . . ? C13B C12B H12B 119.3 . . ? C11B C12B H12B 119.3 . . ? C12B C13B C14B 121.5(2) . . ? C12B C13B H13B 119.2 . . ? C14B C13B H13B 119.2 . . ? C1B C14B C15B 118.7(2) . . ? C1B C14B C13B 122.8(2) . . ? C15B C14B C13B 118.5(2) . . ? C4B C15B C14B 119.9(2) . . ? C4B C15B C16B 120.5(2) . . ? C14B C15B C16B 119.6(2) . . ? C11B C16B C15B 120.4(2) . . ? C11B C16B C7B 120.1(2) . . ? C15B C16B C7B 119.6(2) . . ? O1C C1AC C6AC 123.8(2) . . ? O1C C1AC C2AC 119.6(2) . . ? C6AC C1AC C2AC 116.6(2) . . ? O2C C2AC C3AC 124.1(2) . . ? O2C C2AC C1AC 118.4(2) . . ? C3AC C2AC C1AC 117.5(2) . . ? C4AC C3AC C2AC 121.2(2) . . ? C4AC C3AC Cl1C 122.1(2) . . ? C2AC C3AC Cl1C 116.75(19) . . ? C3AC C4AC C5AC 121.3(2) . . ? C3AC C4AC Cl2C 120.8(2) . . ? C5AC C4AC Cl2C 117.91(19) . . ? C6AC C5AC C4AC 122.3(2) . . ? C6AC C5AC Cl3C 120.3(2) . . ? C4AC C5AC Cl3C 117.30(19) . . ? C5AC C6AC C1AC 121.0(2) . . ? C5AC C6AC Cl4C 123.1(2) . . ? C1AC C6AC Cl4C 115.83(19) . . ? C2C C1C C14C 120.8(2) . . ? C2C C1C H1CA 119.6 . . ? C14C C1C H1CA 119.6 . . ? C1C C2C C3C 120.8(2) . . ? C1C C2C H2CA 119.6 . . ? C3C C2C H2CA 119.6 . . ? C2C C3C C4C 120.4(2) . . ? C2C C3C H3CA 119.8 . . ? C4C C3C H3CA 119.8 . . ? C3C C4C C15C 119.2(2) . . ? C3C C4C C5C 122.3(2) . . ? C15C C4C C5C 118.5(2) . . ? C6C C5C C4C 121.6(2) . . ? C6C C5C H5CA 119.2 . . ? C4C C5C H5CA 119.2 . . ? C5C C6C C7C 121.3(2) . . ? C5C C6C H6CA 119.3 . . ? C7C C6C H6CA 119.3 . . ? C8C C7C C16C 118.8(2) . . ? C8C C7C C6C 122.3(2) . . ? C16C C7C C6C 118.9(2) . . ? C9C C8C C7C 120.6(3) . . ? C9C C8C H8CA 119.7 . . ? C7C C8C H8CA 119.7 . . ? C8C C9C C10C 121.1(3) . . ? C8C C9C H9CA 119.5 . . ? C10C C9C H9CA 119.5 . . ? C9C C10C C11C 120.6(3) . . ? C9C C10C H10C 119.7 . . ? C11C C10C H10C 119.7 . . ? C10C C11C C16C 119.1(2) . . ? C10C C11C C12C 123.0(2) . . ? C16C C11C C12C 117.9(2) . . ? C13C C12C C11C 121.5(2) . . ? C13C C12C H12C 119.2 . . ? C11C C12C H12C 119.2 . . ? C12C C13C C14C 121.6(2) . . ? C12C C13C H13C 119.2 . . ? C14C C13C H13C 119.2 . . ? C1C C14C C15C 119.0(2) . . ? C1C C14C C13C 122.7(2) . . ? C15C C14C C13C 118.3(2) . . ? C14C C15C C16C 120.5(2) . . ? C14C C15C C4C 119.8(2) . . ? C16C C15C C4C 119.7(2) . . ? C15C C16C C11C 120.2(2) . . ? C15C C16C C7C 120.0(2) . . ? C11C C16C C7C 119.8(2) . . ? O1D C1AD C6AD 123.6(3) . . ? O1D C1AD C2AD 118.7(2) . . ? C6AD C1AD C2AD 117.7(2) . . ? O2D C2AD C3AD 124.4(2) . . ? O2D C2AD C1AD 119.4(2) . . ? C3AD C2AD C1AD 116.2(2) . . ? C4AD C3AD C2AD 121.7(2) . . ? C4AD C3AD Cl1D 122.6(2) . . ? C2AD C3AD Cl1D 115.72(19) . . ? C3AD C4AD C5AD 121.9(2) . . ? C3AD C4AD Cl2D 121.0(2) . . ? C5AD C4AD Cl2D 117.12(18) . . ? C6AD C5AD C4AD 121.6(2) . . ? C6AD C5AD Cl3D 120.5(2) . . ? C4AD C5AD Cl3D 117.89(18) . . ? C5AD C6AD C1AD 120.9(2) . . ? C5AD C6AD Cl4D 122.6(2) . . ? C1AD C6AD Cl4D 116.47(19) . . ? C2D C1D C14D 120.9(3) . . ? C2D C1D H1DA 119.6 . . ? C14D C1D H1DA 119.6 . . ? C1D C2D C3D 120.6(3) . . ? C1D C2D H2DA 119.7 . . ? C3D C2D H2DA 119.7 . . ? C2D C3D C4D 121.0(3) . . ? C2D C3D H3DA 119.5 . . ? C4D C3D H3DA 119.5 . . ? C3D C4D C15D 118.9(3) . . ? C3D C4D C5D 122.8(3) . . ? C15D C4D C5D 118.3(3) . . ? C6D C5D C4D 121.8(3) . . ? C6D C5D H5DA 119.1 . . ? C4D C5D H5DA 119.1 . . ? C5D C6D C7D 120.9(3) . . ? C5D C6D H6DA 119.5 . . ? C7D C6D H6DA 119.5 . . ? C8D C7D C16D 118.8(3) . . ? C8D C7D C6D 122.6(3) . . ? C16D C7D C6D 118.6(3) . . ? C9D C8D C7D 121.1(3) . . ? C9D C8D H8DA 119.5 . . ? C7D C8D H8DA 119.5 . . ? C8D C9D C10D 120.7(3) . . ? C8D C9D H9DA 119.7 . . ? C10D C9D H9DA 119.7 . . ? C9D C10D C11D 120.6(3) . . ? C9D C10D H10D 119.7 . . ? C11D C10D H10D 119.7 . . ? C10D C11D C16D 119.0(3) . . ? C10D C11D C12D 122.7(3) . . ? C16D C11D C12D 118.3(3) . . ? C13D C12D C11D 122.2(3) . . ? C13D C12D H12D 118.9 . . ? C11D C12D H12D 118.9 . . ? C12D C13D C14D 121.1(3) . . ? C12D C13D H13D 119.5 . . ? C14D C13D H13D 119.5 . . ? C1D C14D C15D 118.7(3) . . ? C1D C14D C13D 122.7(3) . . ? C15D C14D C13D 118.6(3) . . ? C16D C15D C14D 120.1(2) . . ? C16D C15D C4D 120.0(3) . . ? C14D C15D C4D 119.9(3) . . ? C7D C16D C15D 120.4(2) . . ? C7D C16D C11D 119.8(3) . . ? C15D C16D C11D 119.8(3) . . ? C2E C1E C14E 120.2(2) . . ? C2E C1E H1EA 119.9 . . ? C14E C1E H1EA 119.9 . . ? C3E C2E C1E 120.5(3) . . ? C3E C2E H2EA 119.8 . . ? C1E C2E H2EA 119.8 . . ? C2E C3E C4E 121.2(3) . . ? C2E C3E H3EA 119.4 . . ? C4E C3E H3EA 119.4 . . ? C3E C4E C15E 118.8(2) . . ? C3E C4E C5E 122.2(2) . . ? C15E C4E C5E 118.9(2) . . ? C6E C5E C4E 121.3(2) . . ? C6E C5E H5EA 119.4 . . ? C4E C5E H5EA 119.4 . . ? C5E C6E C7E 121.5(2) . . ? C5E C6E H6EA 119.3 . . ? C7E C6E H6EA 119.2 . . ? C8E C7E C16E 119.1(2) . . ? C8E C7E C6E 122.4(2) . . ? C16E C7E C6E 118.5(2) . . ? C9E C8E C7E 120.6(3) . . ? C9E C8E H8EA 119.7 . . ? C7E C8E H8EA 119.7 . . ? C10E C9E C8E 120.6(3) . . ? C10E C9E H9EA 119.7 . . ? C8E C9E H9EA 119.7 . . ? C9E C10E C11E 120.9(3) . . ? C9E C10E H10E 119.6 . . ? C11E C10E H10E 119.6 . . ? C10E C11E C16E 119.1(2) . . ? C10E C11E C12E 122.8(2) . . ? C16E C11E C12E 118.1(2) . . ? C13E C12E C11E 121.6(2) . . ? C13E C12E H12E 119.2 . . ? C11E C12E H12E 119.2 . . ? C12E C13E C14E 121.3(2) . . ? C12E C13E H13E 119.3 . . ? C14E C13E H13E 119.3 . . ? C1E C14E C15E 119.6(2) . . ? C1E C14E C13E 122.2(2) . . ? C15E C14E C13E 118.3(2) . . ? C14E C15E C16E 120.3(2) . . ? C14E C15E C4E 119.7(2) . . ? C16E C15E C4E 120.0(2) . . ? C11E C16E C7E 119.8(2) . . ? C11E C16E C15E 120.4(2) . . ? C7E C16E C15E 119.8(2) . . ? C2F C1F C14F 121.0(3) . . ? C2F C1F H1FA 119.5 . . ? C14F C1F H1FA 119.5 . . ? C1F C2F C3F 121.0(3) . . ? C1F C2F H2FA 119.5 . . ? C3F C2F H2FA 119.5 . . ? C2F C3F C4F 120.4(3) . . ? C2F C3F H3FA 119.8 . . ? C4F C3F H3FA 119.8 . . ? C3F C4F C15F 119.2(3) . . ? C3F C4F C5F 122.9(3) . . ? C15F C4F C5F 117.9(3) . . ? C6F C5F C4F 121.9(2) . . ? C6F C5F H5FA 119.1 . . ? C4F C5F H5FA 119.1 . . ? C5F C6F C7F 121.0(3) . . ? C5F C6F H6FA 119.5 . . ? C7F C6F H6FA 119.5 . . ? C8F C7F C16F 119.0(3) . . ? C8F C7F C6F 122.0(3) . . ? C16F C7F C6F 119.0(3) . . ? C9F C8F C7F 120.5(3) . . ? C9F C8F H8FA 119.8 . . ? C7F C8F H8FA 119.8 . . ? C10F C9F C8F 120.6(3) . . ? C10F C9F H9FA 119.7 . . ? C8F C9F H9FA 119.7 . . ? C9F C10F C11F 121.0(3) . . ? C9F C10F H10F 119.5 . . ? C11F C10F H10F 119.5 . . ? C10F C11F C16F 118.5(3) . . ? C10F C11F C12F 122.9(3) . . ? C16F C11F C12F 118.6(2) . . ? C13F C12F C11F 121.8(2) . . ? C13F C12F H12F 119.1 . . ? C11F C12F H12F 119.1 . . ? C12F C13F C14F 121.6(3) . . ? C12F C13F H13F 119.2 . . ? C14F C13F H13F 119.2 . . ? C1F C14F C15F 118.9(3) . . ? C1F C14F C13F 123.1(3) . . ? C15F C14F C13F 117.9(3) . . ? C16F C15F C4F 120.0(2) . . ? C16F C15F C14F 120.6(2) . . ? C4F C15F C14F 119.4(3) . . ? C7F C16F C15F 120.2(2) . . ? C7F C16F C11F 120.4(3) . . ? C15F C16F C11F 119.4(2) . . ? _diffrn_measured_fraction_theta_max 0.927 _diffrn_reflns_theta_full 30.00 _diffrn_measured_fraction_theta_full 0.997 _refine_diff_density_max 0.846 _refine_diff_density_min -0.327 _refine_diff_density_rms 0.094 # Attachment 'TTF-CA-adduct.cif' data_ros39 _database_code_depnum_ccdc_archive 'CCDC 611969' _audit_creation_method SHELXL-97 _chemical_name_systematic ; 5',6',7',8'-Tetrachlorodispiro(1,3-dithiole-2,2'-(1,4)benzodioxine-3',2''-(1,3 )dithiole) dichloromethane solvate ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C26 H12 Cl12 O4 S8' _chemical_formula_weight 1070.24 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' 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' Cl Cl 0.1484 0.1585 '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 17.000(5) _cell_length_b 13.405(4) _cell_length_c 17.205(5) _cell_angle_alpha 90.00 _cell_angle_beta 97.907(10) _cell_angle_gamma 90.00 _cell_volume 3883(2) _cell_formula_units_Z 4 _cell_measurement_temperature 173(2) _cell_measurement_reflns_used 1148 _cell_measurement_theta_min 2.37 _cell_measurement_theta_max 25.53 _exptl_crystal_description plate _exptl_crystal_colour colorless _exptl_crystal_size_min 0.05 _exptl_crystal_size_mid 0.20 _exptl_crystal_size_max 0.50 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.831 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 2128 _exptl_absorpt_coefficient_mu 1.321 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.397 _exptl_absorpt_correction_T_max 0.513 _exptl_absorpt_process_details 'Semi-empirical (SADABS procedure)' _exptl_special_details ; ? ; _diffrn_ambient_temperature 173(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 SMART' _diffrn_measurement_method ; \w-scan, frame range 0.3 deg, hemisphere ; _diffrn_standards_number none _diffrn_standards_interval_count 0 _diffrn_standards_interval_time 0 _diffrn_standards_decay_% 0 _diffrn_reflns_number 8301 _diffrn_reflns_av_R_equivalents 0.0473 _diffrn_reflns_av_sigmaI/netI 0.1097 _diffrn_reflns_limit_h_min -23 _diffrn_reflns_limit_h_max 12 _diffrn_reflns_limit_k_min -17 _diffrn_reflns_limit_k_max 11 _diffrn_reflns_limit_l_min -3 _diffrn_reflns_limit_l_max 24 _diffrn_reflns_theta_min 1.93 _diffrn_reflns_theta_max 29.99 _reflns_number_total 6663 _reflns_number_gt 3800 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'SMART V5.630 (BrukerAXS, 1997-2001)' _computing_cell_refinement 'SAINT V6.28 (BrukerAXS, 1997-2001)' _computing_data_reduction 'SAINT & SADABS V2.06 (Sheldrick, 2000)' _computing_structure_solution 'SHELXTL v. 6.12 (Sheldrick, 2001)' _computing_structure_refinement 'SHELXTL v. 6.12 (Sheldrick, 2001)' _computing_molecular_graphics 'XP V5.06 (BrukerAXS, 1997-99)' _computing_publication_material 'SHELXL-93, XCIF V5.05 (BrukerAXS, 1997-99)' _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. 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 _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0431P)^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 6663 _refine_ls_number_parameters 451 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.1004 _refine_ls_R_factor_gt 0.0564 _refine_ls_wR_factor_ref 0.1221 _refine_ls_wR_factor_gt 0.1074 _refine_ls_goodness_of_fit_ref 0.836 _refine_ls_restrained_S_all 0.836 _refine_ls_shift/su_max 0.000 _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 Cl1 Cl 0.15834(10) 0.69729(11) 0.12897(7) 0.0287(4) Uani 1 1 d . . . Cl2 Cl 0.28086(10) 0.78201(11) 0.26576(8) 0.0334(4) Uani 1 1 d . . . Cl3 Cl 0.24547(12) 0.76218(13) 0.43806(8) 0.0411(5) Uani 1 1 d . . . Cl4 Cl 0.09778(10) 0.63754(11) 0.47390(7) 0.0311(4) Uani 1 1 d . . . S1 S -0.11338(11) 0.67129(11) 0.25366(8) 0.0266(4) Uani 1 1 d . . . S2 S -0.13200(11) 0.46389(12) 0.30699(8) 0.0322(4) Uani 1 1 d . . . S3 S 0.02076(10) 0.39565(11) 0.21993(7) 0.0248(4) Uani 1 1 d . . . S4 S -0.10146(11) 0.50165(12) 0.11409(7) 0.0294(4) Uani 1 1 d . . . O1 O 0.0012(3) 0.5602(3) 0.33633(17) 0.0238(10) Uani 1 1 d . . . O2 O 0.0261(2) 0.5910(3) 0.17985(17) 0.0207(10) Uani 1 1 d . . . C1 C 0.1433(4) 0.6817(4) 0.2250(3) 0.0216(15) Uani 1 1 d . . . C2 C 0.1964(4) 0.7215(4) 0.2860(3) 0.0214(15) Uani 1 1 d . . . C3 C 0.1812(4) 0.7089(4) 0.3627(3) 0.0236(16) Uani 1 1 d . . . C4 C 0.1175(4) 0.6548(4) 0.3792(3) 0.0184(14) Uani 1 1 d . . . C5 C 0.0646(4) 0.6143(4) 0.3180(3) 0.0150(14) Uani 1 1 d . . . C6 C 0.0777(4) 0.6288(4) 0.2415(3) 0.0150(13) Uani 1 1 d . . . C7 C -0.0281(4) 0.5162(4) 0.2005(3) 0.0186(14) Uani 1 1 d . . . C8 C -0.0631(4) 0.5507(4) 0.2731(3) 0.0224(16) Uani 1 1 d . . . C9 C -0.1817(4) 0.6492(5) 0.3180(3) 0.0308(17) Uani 1 1 d . . . H9 H -0.2118 0.7021 0.3359 0.037 Uiso 1 1 calc R . . C10 C -0.1905(4) 0.5560(5) 0.3414(3) 0.0373(18) Uani 1 1 d . . . H10 H -0.2277 0.5400 0.3759 0.045 Uiso 1 1 calc R . . C11 C -0.0495(4) 0.4060(4) 0.0745(3) 0.0332(18) Uani 1 1 d . . . H11 H -0.0607 0.3885 0.0206 0.040 Uiso 1 1 calc R . . C12 C 0.0064(4) 0.3586(4) 0.1223(3) 0.0311(18) Uani 1 1 d . . . H12 H 0.0371 0.3067 0.1038 0.037 Uiso 1 1 calc R . . Cl5 Cl 0.64890(11) 0.01980(12) 0.14172(7) 0.0348(4) Uani 1 1 d . . . Cl6 Cl 0.77720(10) -0.05803(11) 0.27709(8) 0.0337(4) Uani 1 1 d . . . Cl7 Cl 0.75058(11) -0.02677(13) 0.45115(8) 0.0399(5) Uani 1 1 d . . . Cl8 Cl 0.59808(11) 0.08785(13) 0.48798(7) 0.0378(5) Uani 1 1 d . . . S5 S 0.35579(11) 0.23936(12) 0.32421(8) 0.0306(4) Uani 1 1 d . . . S6 S 0.38223(10) 0.03054(11) 0.27806(7) 0.0257(4) Uani 1 1 d . . . S7 S 0.37855(11) 0.19068(12) 0.13162(7) 0.0292(4) Uani 1 1 d . . . S8 S 0.50203(11) 0.31113(11) 0.22607(8) 0.0304(4) Uani 1 1 d . . . O3 O 0.4938(3) 0.1530(3) 0.35196(18) 0.0244(10) Uani 1 1 d . . . O4 O 0.5131(2) 0.1145(3) 0.19490(17) 0.0201(10) Uani 1 1 d . . . C13 C 0.6366(4) 0.0364(4) 0.2386(3) 0.0198(15) Uani 1 1 d . . . C14 C 0.6931(4) 0.0020(4) 0.2992(3) 0.0228(15) Uani 1 1 d . . . C15 C 0.6811(4) 0.0196(4) 0.3762(3) 0.0256(16) Uani 1 1 d . . . C16 C 0.6156(4) 0.0697(4) 0.3935(3) 0.0243(16) Uani 1 1 d . . . C17 C 0.5589(4) 0.1031(4) 0.3329(3) 0.0217(15) Uani 1 1 d . . . C18 C 0.5702(4) 0.0854(4) 0.2557(3) 0.0159(14) Uani 1 1 d . . . C19 C 0.4565(4) 0.1873(4) 0.2146(3) 0.0224(15) Uani 1 1 d . . . C20 C 0.4262(4) 0.1552(4) 0.2908(3) 0.0224(15) Uani 1 1 d . . . C21 C 0.3014(4) 0.1454(5) 0.3626(3) 0.0312(17) Uani 1 1 d . . . H21 H 0.2644 0.1611 0.3975 0.037 Uiso 1 1 calc R . . C22 C 0.3127(4) 0.0518(5) 0.3422(3) 0.0306(17) Uani 1 1 d . . . H22 H 0.2842 -0.0015 0.3616 0.037 Uiso 1 1 calc R . . C23 C 0.4188(5) 0.2923(4) 0.0865(3) 0.0351(19) Uani 1 1 d . . . H23 H 0.4017 0.3082 0.0331 0.042 Uiso 1 1 calc R . . C24 C 0.4736(4) 0.3457(4) 0.1291(3) 0.0313(17) Uani 1 1 d . . . H24 H 0.4969 0.4017 0.1073 0.038 Uiso 1 1 calc R . . Cl9 Cl 0.51824(14) 0.14298(14) 0.98644(9) 0.0585(6) Uani 1 1 d . . . Cl10 Cl 0.65365(16) 0.12958(17) 0.90202(11) 0.0764(7) Uani 1 1 d . . . C25 C 0.5698(6) 0.0723(6) 0.9267(4) 0.076(3) Uani 1 1 d . . . H25A H 0.5854 0.0086 0.9535 0.091 Uiso 1 1 calc R . . H25B H 0.5340 0.0563 0.8779 0.091 Uiso 1 1 calc R . . Cl11 Cl 0.7951(2) 0.8954(2) 0.05833(18) 0.1366(15) Uani 1 1 d . . . Cl12 Cl 0.91334(19) 0.74865(16) 0.04655(14) 0.1008(10) Uani 1 1 d . . . C26 C 0.8914(6) 0.8724(5) 0.0420(4) 0.065(3) Uani 1 1 d . . . H26A H 0.8989 0.8983 -0.0104 0.079 Uiso 1 1 calc R . . H26B H 0.9285 0.9084 0.0817 0.079 Uiso 1 1 calc 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 Cl1 0.0343(13) 0.0290(9) 0.0238(6) 0.0029(5) 0.0071(6) -0.0019(8) Cl2 0.0214(13) 0.0270(9) 0.0513(8) 0.0015(7) 0.0031(8) -0.0050(8) Cl3 0.0349(15) 0.0461(11) 0.0361(8) -0.0079(7) -0.0169(7) -0.0120(9) Cl4 0.0402(13) 0.0334(9) 0.0178(6) -0.0036(5) -0.0024(6) -0.0014(8) S1 0.0251(13) 0.0225(9) 0.0313(7) -0.0030(6) -0.0002(7) 0.0005(8) S2 0.0314(14) 0.0278(9) 0.0376(8) -0.0005(6) 0.0051(7) -0.0126(9) S3 0.0272(13) 0.0197(8) 0.0261(6) -0.0002(5) -0.0014(6) 0.0012(8) S4 0.0287(14) 0.0280(9) 0.0274(7) -0.0053(6) -0.0109(7) -0.0024(8) O1 0.023(3) 0.028(2) 0.0185(17) 0.0030(15) -0.0048(17) -0.005(2) O2 0.018(3) 0.023(2) 0.0183(16) -0.0026(14) -0.0071(16) -0.009(2) C1 0.025(5) 0.019(3) 0.021(2) 0.001(2) 0.004(2) 0.007(3) C2 0.010(5) 0.016(3) 0.037(3) 0.003(2) -0.001(3) 0.004(3) C3 0.023(5) 0.017(3) 0.028(3) -0.006(2) -0.009(3) 0.002(3) C4 0.017(5) 0.018(3) 0.018(2) 0.001(2) -0.004(2) 0.001(3) C5 0.005(4) 0.014(3) 0.025(2) -0.002(2) -0.001(2) -0.003(3) C6 0.007(4) 0.015(3) 0.021(2) -0.001(2) -0.006(2) 0.000(3) C7 0.009(5) 0.015(3) 0.029(3) 0.001(2) -0.005(2) 0.000(3) C8 0.025(5) 0.018(3) 0.022(2) 0.002(2) -0.005(3) 0.000(3) C9 0.015(5) 0.042(4) 0.034(3) -0.010(3) -0.002(3) -0.003(3) C10 0.021(5) 0.058(5) 0.033(3) -0.008(3) 0.004(3) -0.011(4) C11 0.043(6) 0.026(4) 0.029(3) -0.007(2) -0.003(3) -0.004(4) C12 0.046(6) 0.019(3) 0.028(3) -0.009(2) 0.005(3) -0.002(3) Cl5 0.0367(13) 0.0402(10) 0.0280(6) -0.0051(6) 0.0063(7) 0.0086(9) Cl6 0.0233(13) 0.0277(9) 0.0499(8) 0.0019(7) 0.0034(8) 0.0047(8) Cl7 0.0262(14) 0.0500(11) 0.0394(8) 0.0158(7) -0.0102(7) -0.0002(9) Cl8 0.0336(14) 0.0566(12) 0.0213(6) -0.0005(6) -0.0026(7) -0.0065(9) S5 0.0257(13) 0.0288(9) 0.0368(7) -0.0057(6) 0.0034(7) 0.0072(8) S6 0.0239(13) 0.0213(9) 0.0308(7) -0.0003(6) -0.0005(7) -0.0032(8) S7 0.0237(13) 0.0342(10) 0.0272(7) 0.0041(6) -0.0055(7) 0.0011(8) S8 0.0311(14) 0.0192(9) 0.0406(8) -0.0011(6) 0.0033(7) -0.0024(8) O3 0.016(3) 0.029(2) 0.0266(18) -0.0074(16) -0.0050(17) 0.005(2) O4 0.015(3) 0.020(2) 0.0232(17) -0.0018(15) -0.0041(17) 0.006(2) C13 0.019(5) 0.015(3) 0.024(2) -0.002(2) -0.001(2) -0.008(3) C14 0.011(5) 0.014(3) 0.043(3) 0.002(2) 0.001(3) -0.001(3) C15 0.022(5) 0.025(4) 0.027(3) 0.009(2) -0.006(3) -0.009(3) C16 0.021(5) 0.028(4) 0.022(3) 0.003(2) -0.004(3) -0.017(3) C17 0.018(5) 0.016(3) 0.030(3) 0.002(2) 0.001(3) -0.001(3) C18 0.009(5) 0.012(3) 0.025(2) 0.004(2) -0.003(2) 0.000(3) C19 0.013(5) 0.021(3) 0.031(3) -0.004(2) -0.004(3) 0.002(3) C20 0.017(5) 0.025(3) 0.023(2) -0.001(2) -0.006(2) 0.004(3) C21 0.021(5) 0.050(4) 0.022(3) 0.007(3) 0.001(3) 0.010(4) C22 0.012(5) 0.049(5) 0.028(3) 0.011(3) -0.005(3) 0.005(3) C23 0.052(6) 0.027(4) 0.027(3) 0.006(2) 0.007(3) 0.013(4) C24 0.040(6) 0.018(3) 0.038(3) 0.004(2) 0.012(3) 0.007(3) Cl9 0.080(2) 0.0438(12) 0.0509(10) 0.0010(8) 0.0081(10) 0.0148(12) Cl10 0.075(2) 0.0841(17) 0.0716(12) -0.0356(12) 0.0152(12) -0.0219(14) C25 0.133(10) 0.052(5) 0.054(4) -0.014(4) 0.050(5) -0.023(6) Cl11 0.156(4) 0.102(2) 0.180(3) 0.058(2) 0.124(3) 0.068(2) Cl12 0.148(3) 0.0521(14) 0.1214(18) 0.0333(13) 0.0879(19) 0.0353(15) C26 0.094(10) 0.048(5) 0.052(4) -0.010(4) 0.003(5) -0.011(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 Cl1 C1 1.719(5) . ? Cl2 C2 1.726(6) . ? Cl3 C3 1.730(6) . ? Cl4 C4 1.723(5) . ? S1 C9 1.737(6) . ? S1 C8 1.838(6) . ? S2 C10 1.740(7) . ? S2 C8 1.804(6) . ? S3 C12 1.737(5) . ? S3 C7 1.826(6) . ? S4 C11 1.748(6) . ? S4 C7 1.815(6) . ? O1 C5 1.372(7) . ? O1 C8 1.438(7) . ? O2 C6 1.377(6) . ? O2 C7 1.438(7) . ? C1 C6 1.383(8) . ? C1 C2 1.394(8) . ? C2 C3 1.389(7) . ? C3 C4 1.365(8) . ? C4 C5 1.398(7) . ? C5 C6 1.379(6) . ? C7 C8 1.527(7) . ? C9 C10 1.327(8) . ? C9 H9 0.9500 . ? C10 H10 0.9500 . ? C11 C12 1.329(8) . ? C11 H11 0.9500 . ? C12 H12 0.9500 . ? Cl5 C13 1.722(5) . ? Cl6 C14 1.728(6) . ? Cl7 C15 1.739(6) . ? Cl8 C16 1.710(5) . ? S5 C21 1.746(6) . ? S5 C20 1.796(6) . ? S6 C22 1.748(6) . ? S6 C20 1.831(6) . ? S7 C23 1.753(6) . ? S7 C19 1.809(6) . ? S8 C24 1.736(5) . ? S8 C19 1.832(6) . ? O3 C17 1.370(7) . ? O3 C20 1.449(7) . ? O4 C18 1.382(6) . ? O4 C19 1.444(7) . ? C13 C18 1.373(8) . ? C13 C14 1.395(8) . ? C14 C15 1.389(7) . ? C15 C16 1.369(9) . ? C16 C17 1.392(8) . ? C17 C18 1.388(6) . ? C19 C20 1.535(7) . ? C21 C22 1.323(8) . ? C21 H21 0.9500 . ? C22 H22 0.9500 . ? C23 C24 1.314(8) . ? C23 H23 0.9500 . ? C24 H24 0.9500 . ? Cl9 C25 1.724(7) . ? Cl10 C25 1.722(9) . ? C25 H25A 0.9900 . ? C25 H25B 0.9900 . ? Cl11 C26 1.727(10) . ? Cl12 C26 1.699(7) . ? C26 H26A 0.9900 . ? C26 H26B 0.9900 . ? 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 C9 S1 C8 94.0(3) . . ? C10 S2 C8 94.6(3) . . ? C12 S3 C7 94.4(3) . . ? C11 S4 C7 94.0(3) . . ? C5 O1 C8 114.3(4) . . ? C6 O2 C7 115.4(4) . . ? C6 C1 C2 119.9(4) . . ? C6 C1 Cl1 119.4(4) . . ? C2 C1 Cl1 120.7(4) . . ? C3 C2 C1 118.9(5) . . ? C3 C2 Cl2 121.2(4) . . ? C1 C2 Cl2 119.9(4) . . ? C4 C3 C2 121.3(5) . . ? C4 C3 Cl3 120.0(4) . . ? C2 C3 Cl3 118.7(5) . . ? C3 C4 C5 119.7(4) . . ? C3 C4 Cl4 122.1(4) . . ? C5 C4 Cl4 118.1(4) . . ? O1 C5 C6 122.0(5) . . ? O1 C5 C4 118.5(4) . . ? C6 C5 C4 119.5(5) . . ? O2 C6 C5 120.9(5) . . ? O2 C6 C1 118.5(4) . . ? C5 C6 C1 120.6(5) . . ? O2 C7 C8 109.0(4) . . ? O2 C7 S4 105.3(3) . . ? C8 C7 S4 113.6(4) . . ? O2 C7 S3 111.8(4) . . ? C8 C7 S3 109.7(3) . . ? S4 C7 S3 107.4(3) . . ? O1 C8 C7 107.7(5) . . ? O1 C8 S2 105.8(3) . . ? C7 C8 S2 114.4(4) . . ? O1 C8 S1 110.2(3) . . ? C7 C8 S1 110.0(3) . . ? S2 C8 S1 108.6(4) . . ? C10 C9 S1 117.8(5) . . ? C10 C9 H9 121.1 . . ? S1 C9 H9 121.1 . . ? C9 C10 S2 118.1(5) . . ? C9 C10 H10 120.9 . . ? S2 C10 H10 120.9 . . ? C12 C11 S4 117.8(4) . . ? C12 C11 H11 121.1 . . ? S4 C11 H11 121.1 . . ? C11 C12 S3 117.1(5) . . ? C11 C12 H12 121.5 . . ? S3 C12 H12 121.5 . . ? C21 S5 C20 94.5(3) . . ? C22 S6 C20 94.3(3) . . ? C23 S7 C19 94.6(3) . . ? C24 S8 C19 94.6(3) . . ? C17 O3 C20 115.0(4) . . ? C18 O4 C19 115.8(4) . . ? C18 C13 C14 120.0(5) . . ? C18 C13 Cl5 118.8(4) . . ? C14 C13 Cl5 121.2(5) . . ? C15 C14 C13 118.7(5) . . ? C15 C14 Cl6 121.6(5) . . ? C13 C14 Cl6 119.6(4) . . ? C16 C15 C14 121.4(5) . . ? C16 C15 Cl7 120.3(4) . . ? C14 C15 Cl7 118.2(5) . . ? C15 C16 C17 119.7(5) . . ? C15 C16 Cl8 121.9(5) . . ? C17 C16 Cl8 118.2(5) . . ? O3 C17 C18 122.3(5) . . ? O3 C17 C16 118.5(5) . . ? C18 C17 C16 119.3(5) . . ? C13 C18 O4 119.0(4) . . ? C13 C18 C17 120.9(5) . . ? O4 C18 C17 120.1(5) . . ? O4 C19 C20 108.9(4) . . ? O4 C19 S7 105.8(3) . . ? C20 C19 S7 112.7(4) . . ? O4 C19 S8 110.6(4) . . ? C20 C19 S8 110.4(3) . . ? S7 C19 S8 108.4(3) . . ? O3 C20 C19 107.5(5) . . ? O3 C20 S5 106.1(3) . . ? C19 C20 S5 114.5(4) . . ? O3 C20 S6 109.8(4) . . ? C19 C20 S6 109.4(3) . . ? S5 C20 S6 109.4(3) . . ? C22 C21 S5 118.6(5) . . ? C22 C21 H21 120.7 . . ? S5 C21 H21 120.7 . . ? C21 C22 S6 117.2(5) . . ? C21 C22 H22 121.4 . . ? S6 C22 H22 121.4 . . ? C24 C23 S7 117.8(4) . . ? C24 C23 H23 121.1 . . ? S7 C23 H23 121.1 . . ? C23 C24 S8 118.2(5) . . ? C23 C24 H24 120.9 . . ? S8 C24 H24 120.9 . . ? Cl10 C25 Cl9 114.1(4) . . ? Cl10 C25 H25A 108.7 . . ? Cl9 C25 H25A 108.7 . . ? Cl10 C25 H25B 108.7 . . ? Cl9 C25 H25B 108.7 . . ? H25A C25 H25B 107.6 . . ? Cl12 C26 Cl11 112.0(5) . . ? Cl12 C26 H26A 109.2 . . ? Cl11 C26 H26A 109.2 . . ? Cl12 C26 H26B 109.2 . . ? Cl11 C26 H26B 109.2 . . ? H26A C26 H26B 107.9 . . ? _diffrn_measured_fraction_theta_max 0.589 _diffrn_reflns_theta_full 29.99 _diffrn_measured_fraction_theta_full 0.589 _refine_diff_density_max 0.806 _refine_diff_density_min -0.708 _refine_diff_density_rms 0.095 # Attachment 'TTF-CA.cif' data_ros444 _database_code_depnum_ccdc_archive 'CCDC 611970' _audit_creation_method SHELXL-97 _chemical_name_systematic ; Tetrathiafulvalene tetrachloro-o-benzoquinnone ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'c6 Cl4 O2, C6 H4 S4' _chemical_formula_sum 'C12 H4 Cl4 O2 S4' _chemical_formula_weight 450.19 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' 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' Cl Cl 0.1484 0.1585 '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 7.170(3) _cell_length_b 16.961(6) _cell_length_c 12.731(5) _cell_angle_alpha 90.00 _cell_angle_beta 97.176(7) _cell_angle_gamma 90.00 _cell_volume 1536.1(10) _cell_formula_units_Z 4 _cell_measurement_temperature 173(2) _cell_measurement_reflns_used 868 _cell_measurement_theta_min 2.89 _cell_measurement_theta_max 27.14 _exptl_crystal_description block _exptl_crystal_colour black _exptl_crystal_size_max 0.20 _exptl_crystal_size_mid 0.20 _exptl_crystal_size_min 0.10 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.947 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 896 _exptl_absorpt_coefficient_mu 1.314 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.762 _exptl_absorpt_correction_T_max 0.862 _exptl_absorpt_process_details 'Semi-empirical (SADABS procedure)' _exptl_special_details ; ? ; _diffrn_ambient_temperature 173(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 SMART' _diffrn_measurement_method ; \w-scan, frame range 0.3 deg, hemisphere ; _diffrn_detector_area_resol_mean ? _diffrn_standards_number none _diffrn_standards_interval_count 0 _diffrn_standards_interval_time 0 _diffrn_standards_decay_% 0 _diffrn_reflns_number 5633 _diffrn_reflns_av_R_equivalents 0.0546 _diffrn_reflns_av_sigmaI/netI 0.1271 _diffrn_reflns_limit_h_min -10 _diffrn_reflns_limit_h_max 5 _diffrn_reflns_limit_k_min -20 _diffrn_reflns_limit_k_max 10 _diffrn_reflns_limit_l_min -17 _diffrn_reflns_limit_l_max 17 _diffrn_reflns_theta_min 2.01 _diffrn_reflns_theta_max 29.86 _reflns_number_total 3901 _reflns_number_gt 2142 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'SMART V5.630 (BrukerAXS, 1997-2001)' _computing_cell_refinement 'SAINT V6.28 (BrukerAXS, 1997-2001)' _computing_data_reduction 'SAINT & SADABS V2.06 (Sheldrick, 2000)' _computing_structure_solution 'SHELXTL v. 6.12 (Sheldrick, 2001)' _computing_structure_refinement 'SHELXTL v. 6.12 (Sheldrick, 2001)' _computing_molecular_graphics 'XP V5.06 (BrukerAXS, 1997-99)' _computing_publication_material 'SHELXL-93, XCIF V5.05 (BrukerAXS, 1997-99)' _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. 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 _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0294P)^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 3901 _refine_ls_number_parameters 199 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0950 _refine_ls_R_factor_gt 0.0485 _refine_ls_wR_factor_ref 0.1003 _refine_ls_wR_factor_gt 0.0900 _refine_ls_goodness_of_fit_ref 0.773 _refine_ls_restrained_S_all 0.773 _refine_ls_shift/su_max 0.000 _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 Cl1 Cl 0.65956(15) 0.27542(6) 0.41719(8) 0.0276(3) Uani 1 1 d . . . Cl2 Cl 0.39626(15) 0.23559(6) 0.20377(8) 0.0264(3) Uani 1 1 d . . . Cl3 Cl 0.33907(14) 0.06255(7) 0.13265(8) 0.0259(3) Uani 1 1 d . . . Cl4 Cl 0.48623(15) -0.07583(6) 0.28375(8) 0.0281(3) Uani 1 1 d . . . O1 O 0.7122(4) -0.01957(17) 0.4756(2) 0.0263(7) Uani 1 1 d . . . O2 O 0.7822(4) 0.13425(17) 0.5345(2) 0.0276(7) Uani 1 1 d . . . C1 C 0.6488(6) 0.0343(3) 0.4173(3) 0.0209(10) Uani 1 1 d . . . C2 C 0.6905(6) 0.1190(3) 0.4493(3) 0.0206(10) Uani 1 1 d . . . C3 C 0.6090(5) 0.1800(2) 0.3764(3) 0.0194(9) Uani 1 1 d . . . C4 C 0.4992(6) 0.1629(3) 0.2848(3) 0.0218(10) Uani 1 1 d . . . C5 C 0.4656(5) 0.0812(3) 0.2536(3) 0.0185(9) Uani 1 1 d . . . C6 C 0.5337(6) 0.0211(2) 0.3181(3) 0.0188(9) Uani 1 1 d . . . S1 S 0.53239(15) 0.59239(7) 0.20284(8) 0.0226(3) Uani 1 1 d . . . S2 S 0.66110(16) 0.48900(7) 0.37988(8) 0.0263(3) Uani 1 1 d . . . S3 S 0.81059(16) 0.63973(7) 0.52054(9) 0.0284(3) Uani 1 1 d . . . S4 S 0.64757(16) 0.74580(7) 0.35344(9) 0.0270(3) Uani 1 1 d . . . C7 C 0.4795(6) 0.4935(3) 0.1878(3) 0.0238(10) Uani 1 1 d . . . H7 H 0.4100 0.4733 0.1251 0.029 Uiso 1 1 calc R . . C8 C 0.5411(6) 0.4477(3) 0.2680(3) 0.0268(11) Uani 1 1 d . . . H8 H 0.5195 0.3924 0.2642 0.032 Uiso 1 1 calc R . . C9 C 0.6386(5) 0.5848(2) 0.3314(3) 0.0189(9) Uani 1 1 d . . . C10 C 0.6953(5) 0.6492(2) 0.3936(3) 0.0206(10) Uani 1 1 d . . . C11 C 0.8247(6) 0.7389(3) 0.5465(3) 0.0281(11) Uani 1 1 d . . . H11 H 0.8823 0.7583 0.6127 0.034 Uiso 1 1 calc R . . C12 C 0.7517(6) 0.7878(3) 0.4702(3) 0.0284(11) Uani 1 1 d . . . H12 H 0.7566 0.8433 0.4795 0.034 Uiso 1 1 calc 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 Cl1 0.0324(6) 0.0173(7) 0.0312(6) -0.0018(5) -0.0040(5) 0.0001(5) Cl2 0.0247(6) 0.0216(7) 0.0305(6) 0.0056(5) -0.0057(4) 0.0053(5) Cl3 0.0240(6) 0.0268(7) 0.0243(5) 0.0008(5) -0.0074(4) -0.0026(5) Cl4 0.0316(6) 0.0188(7) 0.0318(6) 0.0016(5) -0.0042(5) -0.0040(5) O1 0.0285(17) 0.0185(19) 0.0299(17) 0.0061(14) -0.0044(13) 0.0038(14) O2 0.0364(18) 0.0215(19) 0.0225(16) -0.0003(14) -0.0062(13) -0.0005(15) C1 0.021(2) 0.023(3) 0.018(2) 0.0044(19) 0.0011(17) 0.002(2) C2 0.018(2) 0.022(3) 0.022(2) 0.0032(18) 0.0001(17) 0.0049(19) C3 0.018(2) 0.014(3) 0.025(2) 0.0015(18) 0.0029(17) 0.0007(18) C4 0.020(2) 0.023(3) 0.024(2) 0.0036(19) 0.0063(17) 0.0038(19) C5 0.016(2) 0.025(3) 0.0127(19) -0.0013(18) -0.0028(15) 0.0014(19) C6 0.019(2) 0.014(3) 0.023(2) 0.0016(18) -0.0013(17) -0.0015(18) S1 0.0215(6) 0.0223(7) 0.0222(5) 0.0017(5) -0.0047(4) 0.0000(5) S2 0.0320(7) 0.0196(7) 0.0249(6) 0.0024(5) -0.0056(5) -0.0006(5) S3 0.0317(7) 0.0257(8) 0.0255(6) -0.0049(5) -0.0051(5) 0.0010(6) S4 0.0298(6) 0.0183(7) 0.0319(6) -0.0004(5) -0.0003(5) 0.0030(5) C7 0.018(2) 0.029(3) 0.023(2) -0.005(2) -0.0046(17) -0.004(2) C8 0.023(2) 0.021(3) 0.034(3) -0.005(2) -0.005(2) -0.003(2) C9 0.015(2) 0.017(3) 0.024(2) -0.0009(18) -0.0014(16) 0.0019(18) C10 0.020(2) 0.018(3) 0.024(2) 0.0020(19) 0.0003(17) 0.0020(19) C11 0.027(2) 0.025(3) 0.031(2) -0.014(2) -0.0040(19) -0.006(2) C12 0.025(2) 0.022(3) 0.038(3) -0.010(2) 0.006(2) -0.004(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 Cl1 C3 1.724(4) . ? Cl2 C4 1.715(4) . ? Cl3 C5 1.716(4) . ? Cl4 C6 1.723(4) . ? O1 C1 1.227(4) . ? O2 C2 1.224(4) . ? C1 C6 1.437(5) . ? C1 C2 1.513(6) . ? C2 C3 1.463(5) . ? C3 C4 1.354(5) . ? C4 C5 1.453(6) . ? C5 C6 1.362(5) . ? S1 C9 1.722(4) . ? S1 C7 1.725(4) . ? S2 C8 1.718(4) . ? S2 C9 1.738(4) . ? S3 C11 1.715(4) . ? S3 C10 1.729(4) . ? S4 C12 1.731(4) . ? S4 C10 1.737(4) . ? C7 C8 1.316(6) . ? C7 H7 0.9500 . ? C8 H8 0.9500 . ? C9 C10 1.380(5) . ? C11 C12 1.333(6) . ? C11 H11 0.9500 . ? C12 H12 0.9500 . ? 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 O1 C1 C6 122.9(4) . . ? O1 C1 C2 119.9(4) . . ? C6 C1 C2 117.2(4) . . ? O2 C2 C3 122.7(4) . . ? O2 C2 C1 120.4(4) . . ? C3 C2 C1 116.8(3) . . ? C4 C3 C2 122.5(4) . . ? C4 C3 Cl1 122.6(3) . . ? C2 C3 Cl1 114.9(3) . . ? C3 C4 C5 120.0(4) . . ? C3 C4 Cl2 121.6(4) . . ? C5 C4 Cl2 118.5(3) . . ? C6 C5 C4 120.9(3) . . ? C6 C5 Cl3 120.9(3) . . ? C4 C5 Cl3 118.2(3) . . ? C5 C6 C1 122.5(4) . . ? C5 C6 Cl4 121.1(3) . . ? C1 C6 Cl4 116.5(3) . . ? C9 S1 C7 95.6(2) . . ? C8 S2 C9 94.2(2) . . ? C11 S3 C10 95.6(2) . . ? C12 S4 C10 95.0(2) . . ? C8 C7 S1 116.1(3) . . ? C8 C7 H7 121.9 . . ? S1 C7 H7 121.9 . . ? C7 C8 S2 119.2(4) . . ? C7 C8 H8 120.4 . . ? S2 C8 H8 120.4 . . ? C10 C9 S1 123.3(3) . . ? C10 C9 S2 122.0(3) . . ? S1 C9 S2 114.7(2) . . ? C9 C10 S3 122.3(3) . . ? C9 C10 S4 123.0(3) . . ? S3 C10 S4 114.6(2) . . ? C12 C11 S3 117.5(3) . . ? C12 C11 H11 121.3 . . ? S3 C11 H11 121.3 . . ? C11 C12 S4 117.3(4) . . ? C11 C12 H12 121.4 . . ? S4 C12 H12 121.4 . . ? _diffrn_measured_fraction_theta_max 0.883 _diffrn_reflns_theta_full 29.00 _diffrn_measured_fraction_theta_full 0.901 _refine_diff_density_max 0.710 _refine_diff_density_min -0.442 _refine_diff_density_rms 0.114 # Attachment 'TTF-CB-ET2O.cif' data_ros41m _database_code_depnum_ccdc_archive 'CCDC 611971' _audit_creation_method SHELXL-97 _chemical_name_systematic ; Tetrathiafulvalenium Dodecamethylcarba-closo-dodecaboranate diethylether disolvate ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C35 H80 B11 O4 S4' _chemical_formula_weight 812.14 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' B B 0.0013 0.0007 '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' O O 0.0106 0.0060 '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 10.587(5) _cell_length_b 11.677(5) _cell_length_c 12.740(6) _cell_angle_alpha 63.152(7) _cell_angle_beta 67.095(8) _cell_angle_gamma 68.555(8) _cell_volume 1259.4(10) _cell_formula_units_Z 1 _cell_measurement_temperature 173(2) _cell_measurement_reflns_used 6806 _cell_measurement_theta_min 0.00 _cell_measurement_theta_max 0.00 _exptl_crystal_description block _exptl_crystal_colour orange _exptl_crystal_size_max 0.50 _exptl_crystal_size_mid 0.20 _exptl_crystal_size_min 0.10 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.071 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 441 _exptl_absorpt_coefficient_mu 0.221 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min ? _exptl_absorpt_correction_T_max ? _exptl_absorpt_process_details ? _exptl_special_details ; Tmin/Tmax ratio from multi-scan correction: 0.893 SADABS (Sheldrick, 2001) ; _diffrn_ambient_temperature 173(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 'CCD area detector' _diffrn_measurement_method 'phi and omega scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number none _diffrn_standards_interval_count 0 _diffrn_standards_interval_time 0 _diffrn_standards_decay_% 0 _diffrn_reflns_number 19065 _diffrn_reflns_av_R_equivalents 0.0900 _diffrn_reflns_av_sigmaI/netI 0.0705 _diffrn_reflns_limit_h_min -14 _diffrn_reflns_limit_h_max 14 _diffrn_reflns_limit_k_min -16 _diffrn_reflns_limit_k_max 16 _diffrn_reflns_limit_l_min -17 _diffrn_reflns_limit_l_max 17 _diffrn_reflns_theta_min 1.86 _diffrn_reflns_theta_max 30.06 _reflns_number_total 7248 _reflns_number_gt 5370 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'Bruker SMART' _computing_data_reduction 'Bruker SAINT' _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. 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 _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0821P)^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 7248 _refine_ls_number_parameters 304 _refine_ls_number_restraints 1 _refine_ls_R_factor_all 0.0628 _refine_ls_R_factor_gt 0.0485 _refine_ls_wR_factor_ref 0.1444 _refine_ls_wR_factor_gt 0.1363 _refine_ls_goodness_of_fit_ref 0.985 _refine_ls_restrained_S_all 0.985 _refine_ls_shift/su_max 0.023 _refine_ls_shift/su_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_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 0.57834(3) 0.87444(4) 0.39292(3) 0.03435(11) Uani 1 1 d . . . S2 S 0.29614(3) 1.00906(4) 0.49156(3) 0.03599(11) Uani 1 1 d . . . C1 C 0.47292(13) 0.97521(12) 0.47461(11) 0.0268(3) Uani 1 1 d . . . C2 C 0.44196(16) 0.85645(15) 0.36365(14) 0.0376(3) Uani 1 1 d . . . H2 H 0.4585 0.8048 0.3176 0.045 Uiso 1 1 calc R . . C3 C 0.31223(16) 0.91868(15) 0.40895(14) 0.0392(3) Uani 1 1 d . . . H3 H 0.2321 0.9135 0.3963 0.047 Uiso 1 1 calc R . . B1 B 0.47474(17) 0.58258(16) 0.09002(13) 0.0320(3) Uani 1 1 d . . . B2 B 0.36442(17) 0.47816(16) 0.12764(14) 0.0339(3) Uani 1 1 d . . . B3 B 0.35914(17) 0.62818(16) -0.00028(15) 0.0341(3) Uani 1 1 d . . . B4 B 0.53290(17) 0.65070(15) -0.07180(14) 0.0327(3) Uani 1 1 d . . . B6 B 0.54185(17) 0.40948(16) 0.13367(13) 0.0332(3) Uani 1 1 d . . . C4 C 0.45050(19) 0.66132(18) 0.17395(15) 0.0484(4) Uani 1 1 d . . . H4A H 0.3896 0.6227 0.2551 0.073 Uiso 1 1 calc R . . H4B H 0.4055 0.7541 0.1366 0.073 Uiso 1 1 calc R . . H4C H 0.5415 0.6554 0.1816 0.073 Uiso 1 1 calc R . . C5 C 0.23701(19) 0.4551(2) 0.24928(16) 0.0552(4) Uani 1 1 d . . . H5A H 0.2215 0.3670 0.2770 0.083 Uiso 1 1 calc R . . H5B H 0.1513 0.5218 0.2323 0.083 Uiso 1 1 calc R . . H5C H 0.2601 0.4623 0.3131 0.083 Uiso 1 1 calc R . . C6 C 0.22651(19) 0.75023(18) -0.00141(18) 0.0545(4) Uani 1 1 d . . . H6A H 0.2014 0.7698 0.0723 0.082 Uiso 1 1 calc R . . H6B H 0.1466 0.7285 -0.0034 0.082 Uiso 1 1 calc R . . H6C H 0.2499 0.8275 -0.0738 0.082 Uiso 1 1 calc R . . C7 C 0.5650(2) 0.79457(17) -0.13994(16) 0.0544(4) Uani 1 1 d . . . H7A H 0.4966 0.8542 -0.1870 0.082 Uiso 1 1 calc R . . H7B H 0.6604 0.7895 -0.1952 0.082 Uiso 1 1 calc R . . H7C H 0.5576 0.8281 -0.0793 0.082 Uiso 1 1 calc R . . B5 B 0.64549(17) 0.51620(16) 0.01028(14) 0.0367(3) Uani 0.50 1 d P . 1 C8A C 0.78391(19) 0.5320(2) 0.02005(18) 0.0541(4) Uani 0.50 1 d P A 1 H8A1 H 0.7979 0.4750 0.1013 0.081 Uiso 0.50 1 calc PR A 1 H8A2 H 0.7728 0.6241 0.0072 0.081 Uiso 0.50 1 calc PR A 1 H8A3 H 0.8658 0.5066 -0.0423 0.081 Uiso 0.50 1 calc PR A 1 C18 C 0.64549(17) 0.51620(16) 0.01028(14) 0.0367(3) Uani 0.50 1 d P . 2 C8B C 0.78391(19) 0.5320(2) 0.02005(18) 0.0541(4) Uani 0.50 1 d P B 2 H8B1 H 0.7615 0.5501 0.0941 0.081 Uiso 0.50 1 calc PR B 2 H8B2 H 0.8179 0.6053 -0.0517 0.081 Uiso 0.50 1 calc PR B 2 H8B3 H 0.8572 0.4503 0.0237 0.081 Uiso 0.50 1 calc PR B 2 C9 C 0.5823(2) 0.32248(18) 0.26019(15) 0.0541(4) Uani 1 1 d . . . H9A H 0.4969 0.3239 0.3282 0.081 Uiso 1 1 calc R . . H9B H 0.6483 0.3588 0.2661 0.081 Uiso 1 1 calc R . . H9C H 0.6266 0.2314 0.2639 0.081 Uiso 1 1 calc R . . O1 O 0.98042(11) 0.02049(12) 0.65914(10) 0.0463(3) Uani 1 1 d . . . C10 C 1.0069(2) -0.2054(2) 0.6945(2) 0.0643(5) Uani 1 1 d . . . H10A H 0.9317 -0.1767 0.6553 0.096 Uiso 1 1 calc R . . H10B H 1.0033 -0.2927 0.7587 0.096 Uiso 1 1 calc R . . H10C H 1.0985 -0.2101 0.6335 0.096 Uiso 1 1 calc R . . C11 C 0.9881(3) -0.1119(2) 0.74785(17) 0.0750(6) Uani 1 1 d . . . H11A H 0.9005 -0.1144 0.8155 0.090 Uiso 1 1 calc R . . H11B H 1.0679 -0.1377 0.7823 0.090 Uiso 1 1 calc R . . C12 C 0.9737(3) 0.1143(3) 0.7029(2) 0.0821(7) Uani 1 1 d . . . H12A H 1.0589 0.0895 0.7301 0.098 Uiso 1 1 calc R . . H12B H 0.8904 0.1155 0.7740 0.098 Uiso 1 1 calc R . . C13 C 0.9640(3) 0.2457(3) 0.6074(3) 0.0869(8) Uani 1 1 d . . . H13A H 1.0493 0.2459 0.5392 0.130 Uiso 1 1 calc R . . H13B H 0.9545 0.3104 0.6406 0.130 Uiso 1 1 calc R . . H13C H 0.8815 0.2688 0.5784 0.130 Uiso 1 1 calc R . . O2 O 0.7351(4) 0.6866(4) 0.2695(4) 0.0455(7) Uani 0.609(7) 1 d P C 1 C14 C 0.7840(10) 0.8719(6) 0.0875(7) 0.083(2) Uani 0.609(7) 1 d P C 1 H14A H 0.7323 0.8630 0.0433 0.125 Uiso 0.609(7) 1 calc PR C 1 H14B H 0.8602 0.9159 0.0287 0.125 Uiso 0.609(7) 1 calc PR C 1 H14C H 0.7195 0.9245 0.1377 0.125 Uiso 0.609(7) 1 calc PR C 1 C15 C 0.8449(4) 0.7380(5) 0.1678(4) 0.0546(11) Uani 0.609(7) 1 d P C 1 H15A H 0.8926 0.6784 0.1210 0.066 Uiso 0.609(7) 1 calc PR C 1 H15B H 0.9155 0.7442 0.1969 0.066 Uiso 0.609(7) 1 calc PR C 1 C16 C 0.7831(8) 0.5555(7) 0.3432(7) 0.0652(17) Uani 0.609(7) 1 d P C 1 H16A H 0.8559 0.5513 0.3762 0.078 Uiso 0.609(7) 1 calc PR C 1 H16B H 0.8258 0.4985 0.2938 0.078 Uiso 0.609(7) 1 calc PR C 1 C17 C 0.6614(7) 0.5079(5) 0.4458(5) 0.0759(15) Uani 0.609(7) 1 d P C 1 H17A H 0.6193 0.5650 0.4940 0.114 Uiso 0.609(7) 1 calc PR C 1 H17B H 0.6945 0.4172 0.4981 0.114 Uiso 0.609(7) 1 calc PR C 1 H17C H 0.5908 0.5102 0.4126 0.114 Uiso 0.609(7) 1 calc PR C 1 O3 O 0.7297(5) 0.7317(7) 0.2191(7) 0.0496(12) Uani 0.391(7) 1 d P C 2 C19 C 0.6892(9) 0.9225(7) 0.0457(6) 0.074(2) Uani 0.391(7) 1 d P C 2 H19A H 0.6362 0.8815 0.0296 0.111 Uiso 0.391(7) 1 calc PR C 2 H19B H 0.7352 0.9834 -0.0317 0.111 Uiso 0.391(7) 1 calc PR C 2 H19C H 0.6246 0.9712 0.0993 0.111 Uiso 0.391(7) 1 calc PR C 2 C20 C 0.7988(9) 0.8177(10) 0.1065(9) 0.061(3) Uani 0.391(7) 1 d P C 2 H20A H 0.8641 0.7675 0.0532 0.073 Uiso 0.391(7) 1 calc PR C 2 H20B H 0.8541 0.8585 0.1214 0.073 Uiso 0.391(7) 1 calc PR C 2 C21 C 0.8253(10) 0.6235(11) 0.2718(9) 0.086(3) Uani 0.391(7) 1 d PD C 2 H21A H 0.8903 0.6519 0.2889 0.103 Uiso 0.391(7) 1 calc PR C 2 H21B H 0.8816 0.5743 0.2160 0.103 Uiso 0.391(7) 1 calc PR C 2 C22 C 0.7424(17) 0.5368(15) 0.3898(11) 0.117(7) Uani 0.391(7) 1 d PD C 2 H22A H 0.7120 0.5742 0.4532 0.176 Uiso 0.391(7) 1 calc PR C 2 H22B H 0.8021 0.4478 0.4160 0.176 Uiso 0.391(7) 1 calc PR C 2 H22C H 0.6595 0.5322 0.3764 0.176 Uiso 0.391(7) 1 calc PR C 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 0.02719(18) 0.0386(2) 0.03603(19) -0.01714(15) -0.00495(13) -0.00544(14) S2 0.02152(17) 0.0406(2) 0.0423(2) -0.01428(16) -0.00803(13) -0.00487(14) C1 0.0215(5) 0.0266(6) 0.0226(5) -0.0030(5) -0.0040(4) -0.0051(5) C2 0.0416(8) 0.0385(8) 0.0378(7) -0.0121(6) -0.0140(6) -0.0133(6) C3 0.0368(7) 0.0413(8) 0.0424(8) -0.0091(6) -0.0164(6) -0.0136(6) B1 0.0334(7) 0.0334(8) 0.0263(7) -0.0053(6) -0.0090(6) -0.0107(6) B2 0.0319(7) 0.0377(8) 0.0277(7) -0.0072(6) -0.0053(6) -0.0124(6) B3 0.0327(8) 0.0330(8) 0.0332(8) -0.0078(6) -0.0118(6) -0.0061(6) B4 0.0353(8) 0.0305(7) 0.0264(7) -0.0024(6) -0.0086(6) -0.0110(6) B6 0.0365(8) 0.0322(7) 0.0255(7) -0.0018(6) -0.0118(6) -0.0096(6) C4 0.0540(10) 0.0527(10) 0.0430(9) -0.0193(8) -0.0129(7) -0.0145(8) C5 0.0473(9) 0.0697(12) 0.0436(9) -0.0213(8) 0.0056(7) -0.0262(9) C6 0.0451(9) 0.0491(10) 0.0650(11) -0.0215(8) -0.0222(8) 0.0029(8) C7 0.0722(12) 0.0414(9) 0.0447(9) -0.0011(7) -0.0168(8) -0.0255(9) B5 0.0339(7) 0.0394(8) 0.0342(7) -0.0083(6) -0.0109(6) -0.0103(6) C8A 0.0442(9) 0.0666(12) 0.0587(10) -0.0207(9) -0.0172(8) -0.0192(9) C18 0.0339(7) 0.0394(8) 0.0342(7) -0.0083(6) -0.0109(6) -0.0103(6) C8B 0.0442(9) 0.0666(12) 0.0587(10) -0.0207(9) -0.0172(8) -0.0192(9) C9 0.0680(12) 0.0498(10) 0.0366(8) 0.0004(7) -0.0252(8) -0.0139(9) O1 0.0315(5) 0.0681(8) 0.0453(6) -0.0284(6) -0.0115(5) -0.0064(5) C10 0.0551(11) 0.0611(12) 0.0649(12) -0.0104(10) -0.0156(9) -0.0173(9) C11 0.0768(15) 0.0887(17) 0.0372(10) -0.0139(10) -0.0129(9) -0.0095(12) C12 0.0798(16) 0.105(2) 0.0873(16) -0.0711(16) -0.0280(13) 0.0041(14) C13 0.0773(16) 0.0782(16) 0.135(2) -0.0740(17) -0.0393(16) 0.0081(13) O2 0.0513(15) 0.0384(16) 0.0428(16) -0.0171(12) -0.0166(14) 0.0012(13) C14 0.105(5) 0.064(4) 0.038(2) -0.009(3) 0.006(2) -0.015(3) C15 0.0488(19) 0.064(3) 0.061(2) -0.036(2) -0.0069(17) -0.0153(18) C16 0.070(3) 0.040(3) 0.086(5) -0.021(3) -0.041(4) 0.006(2) C17 0.108(4) 0.053(2) 0.061(3) -0.001(2) -0.038(3) -0.021(2) O3 0.041(2) 0.055(3) 0.059(3) -0.031(2) -0.013(2) -0.006(2) C19 0.090(5) 0.057(4) 0.058(3) -0.023(3) 0.010(3) -0.029(4) C20 0.040(3) 0.078(8) 0.067(7) -0.041(7) 0.007(4) -0.019(5) C21 0.082(5) 0.089(7) 0.105(8) -0.054(7) -0.057(6) 0.017(5) C22 0.146(17) 0.078(9) 0.078(10) -0.018(7) -0.058(10) 0.043(9) _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 1.7191(14) . ? S1 C2 1.7263(16) . ? S2 C1 1.7110(15) . ? S2 C3 1.7270(17) . ? C1 C1 1.397(3) 2_676 ? C2 C3 1.334(2) . ? C2 H2 0.9500 . ? C3 H3 0.9500 . ? B1 C4 1.599(2) . ? B1 B6 1.773(2) . ? B1 B4 1.775(2) . ? B1 B5 1.777(2) . ? B1 B2 1.777(2) . ? B1 B3 1.781(2) . ? B2 C5 1.599(2) . ? B2 B4 1.767(2) 2_665 ? B2 B6 1.770(2) . ? B2 C18 1.771(2) 2_665 ? B2 B5 1.771(2) 2_665 ? B2 B3 1.774(2) . ? B3 C6 1.593(2) . ? B3 B4 1.765(2) . ? B3 C18 1.766(2) 2_665 ? B3 B5 1.766(2) 2_665 ? B3 B6 1.770(2) 2_665 ? B4 C7 1.601(2) . ? B4 B5 1.760(2) . ? B4 B2 1.767(2) 2_665 ? B4 B6 1.770(2) 2_665 ? B6 C9 1.598(2) . ? B6 B5 1.765(2) . ? B6 B3 1.770(2) 2_665 ? B6 B4 1.770(2) 2_665 ? C4 H4A 0.9800 . ? C4 H4B 0.9800 . ? C4 H4C 0.9800 . ? C5 H5A 0.9800 . ? C5 H5B 0.9800 . ? C5 H5C 0.9800 . ? C6 H6A 0.9800 . ? C6 H6B 0.9800 . ? C6 H6C 0.9800 . ? C7 H7A 0.9800 . ? C7 H7B 0.9800 . ? C7 H7C 0.9800 . ? B5 C8A 1.599(2) . ? B5 B3 1.766(2) 2_665 ? B5 B2 1.771(2) 2_665 ? C8A H8A1 0.9800 . ? C8A H8A2 0.9800 . ? C8A H8A3 0.9800 . ? C9 H9A 0.9800 . ? C9 H9B 0.9800 . ? C9 H9C 0.9800 . ? O1 C12 1.407(2) . ? O1 C11 1.440(2) . ? C10 C11 1.449(3) . ? C10 H10A 0.9800 . ? C10 H10B 0.9800 . ? C10 H10C 0.9800 . ? C11 H11A 0.9900 . ? C11 H11B 0.9900 . ? C12 C13 1.463(4) . ? C12 H12A 0.9900 . ? C12 H12B 0.9900 . ? C13 H13A 0.9800 . ? C13 H13B 0.9800 . ? C13 H13C 0.9800 . ? O2 C16 1.410(8) . ? O2 C15 1.423(5) . ? C14 C15 1.496(6) . ? C14 H14A 0.9800 . ? C14 H14B 0.9800 . ? C14 H14C 0.9800 . ? C15 H15A 0.9900 . ? C15 H15B 0.9900 . ? C16 C17 1.495(8) . ? C16 H16A 0.9900 . ? C16 H16B 0.9900 . ? C17 H17A 0.9800 . ? C17 H17B 0.9800 . ? C17 H17C 0.9800 . ? O3 C21 1.378(9) . ? O3 C20 1.422(10) . ? C19 C20 1.500(11) . ? C19 H19A 0.9800 . ? C19 H19B 0.9800 . ? C19 H19C 0.9800 . ? C20 H20A 0.9900 . ? C20 H20B 0.9900 . ? C21 C22 1.518(9) . ? C21 H21A 0.9900 . ? C21 H21B 0.9900 . ? C22 H22A 0.9800 . ? C22 H22B 0.9800 . ? C22 H22C 0.9800 . ? 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 95.40(7) . . ? C1 S2 C3 95.32(7) . . ? C1 C1 S2 122.07(13) 2_676 . ? C1 C1 S1 122.55(13) 2_676 . ? S2 C1 S1 115.38(8) . . ? C3 C2 S1 116.71(12) . . ? C3 C2 H2 121.6 . . ? S1 C2 H2 121.6 . . ? C2 C3 S2 117.19(12) . . ? C2 C3 H3 121.4 . . ? S2 C3 H3 121.4 . . ? C4 B1 B6 122.50(12) . . ? C4 B1 B4 122.11(13) . . ? B6 B1 B4 107.01(11) . . ? C4 B1 B5 122.46(13) . . ? B6 B1 B5 59.64(9) . . ? B4 B1 B5 59.42(9) . . ? C4 B1 B2 122.12(12) . . ? B6 B1 B2 59.82(9) . . ? B4 B1 B2 107.18(11) . . ? B5 B1 B2 107.27(12) . . ? C4 B1 B3 121.86(13) . . ? B6 B1 B3 107.36(11) . . ? B4 B1 B3 59.53(9) . . ? B5 B1 B3 106.99(12) . . ? B2 B1 B3 59.83(9) . . ? C5 B2 B4 121.27(13) . 2_665 ? C5 B2 B6 121.22(13) . . ? B4 B2 B6 60.07(9) 2_665 . ? C5 B2 C18 122.04(13) . 2_665 ? B4 B2 C18 59.69(9) 2_665 2_665 ? B6 B2 C18 107.80(11) . 2_665 ? C5 B2 B5 122.04(13) . 2_665 ? B4 B2 B5 59.69(9) 2_665 2_665 ? B6 B2 B5 107.80(11) . 2_665 ? C5 B2 B3 122.75(14) . . ? B4 B2 B3 107.45(12) 2_665 . ? B6 B2 B3 107.75(11) . . ? C18 B2 B3 59.77(9) 2_665 . ? B5 B2 B3 59.77(9) 2_665 . ? C5 B2 B1 121.76(14) . . ? B4 B2 B1 108.08(11) 2_665 . ? B6 B2 B1 59.96(9) . . ? C18 B2 B1 108.14(10) 2_665 . ? B5 B2 B1 108.14(10) 2_665 . ? B3 B2 B1 60.18(9) . . ? C6 B3 B4 121.58(13) . . ? C6 B3 C18 122.05(13) . 2_665 ? B4 B3 C18 107.76(12) . 2_665 ? C6 B3 B5 122.05(13) . 2_665 ? B4 B3 B5 107.76(12) . 2_665 ? C6 B3 B6 121.44(13) . 2_665 ? B4 B3 B6 60.11(9) . 2_665 ? C18 B3 B6 59.89(9) 2_665 2_665 ? B5 B3 B6 59.89(9) 2_665 2_665 ? C6 B3 B2 122.07(14) . . ? B4 B3 B2 107.74(11) . . ? C18 B3 B2 60.02(10) 2_665 . ? B5 B3 B2 60.02(10) 2_665 . ? B6 B3 B2 108.03(12) 2_665 . ? C6 B3 B1 121.33(14) . . ? B4 B3 B1 60.07(9) . . ? C18 B3 B1 108.18(11) 2_665 . ? B5 B3 B1 108.18(11) 2_665 . ? B6 B3 B1 108.48(12) 2_665 . ? B2 B3 B1 59.99(9) . . ? C7 B4 B5 121.19(13) . . ? C7 B4 B3 121.68(13) . . ? B5 B4 B3 108.42(11) . . ? C7 B4 B2 121.35(13) . 2_665 ? B5 B4 B2 60.28(10) . 2_665 ? B3 B4 B2 108.41(11) . 2_665 ? C7 B4 B6 121.92(12) . 2_665 ? B5 B4 B6 108.26(12) . 2_665 ? B3 B4 B6 60.07(9) . 2_665 ? B2 B4 B6 60.06(10) 2_665 2_665 ? C7 B4 B1 120.82(13) . . ? B5 B4 B1 60.35(9) . . ? B3 B4 B1 60.40(9) . . ? B2 B4 B1 108.97(11) 2_665 . ? B6 B4 B1 108.70(11) 2_665 . ? C9 B6 B5 121.81(13) . . ? C9 B6 B3 121.26(14) . 2_665 ? B5 B6 B3 59.97(9) . 2_665 ? C9 B6 B2 121.85(13) . . ? B5 B6 B2 108.12(11) . . ? B3 B6 B2 108.06(11) 2_665 . ? C9 B6 B4 121.78(13) . 2_665 ? B5 B6 B4 107.60(11) . 2_665 ? B3 B6 B4 59.83(9) 2_665 2_665 ? B2 B6 B4 59.87(9) . 2_665 ? C9 B6 B1 121.63(14) . . ? B5 B6 B1 60.31(9) . . ? B3 B6 B1 108.55(11) 2_665 . ? B2 B6 B1 60.22(9) . . ? B4 B6 B1 108.12(11) 2_665 . ? B1 C4 H4A 109.5 . . ? B1 C4 H4B 109.5 . . ? H4A C4 H4B 109.5 . . ? B1 C4 H4C 109.5 . . ? H4A C4 H4C 109.5 . . ? H4B C4 H4C 109.5 . . ? B2 C5 H5A 109.5 . . ? B2 C5 H5B 109.5 . . ? H5A C5 H5B 109.5 . . ? B2 C5 H5C 109.5 . . ? H5A C5 H5C 109.5 . . ? H5B C5 H5C 109.5 . . ? B3 C6 H6A 109.5 . . ? B3 C6 H6B 109.5 . . ? H6A C6 H6B 109.5 . . ? B3 C6 H6C 109.5 . . ? H6A C6 H6C 109.5 . . ? H6B C6 H6C 109.5 . . ? B4 C7 H7A 109.5 . . ? B4 C7 H7B 109.5 . . ? H7A C7 H7B 109.5 . . ? B4 C7 H7C 109.5 . . ? H7A C7 H7C 109.5 . . ? H7B C7 H7C 109.5 . . ? C8A B5 B4 121.69(13) . . ? C8A B5 B6 121.61(12) . . ? B4 B5 B6 107.98(11) . . ? C8A B5 B3 121.74(13) . 2_665 ? B4 B5 B3 108.07(11) . 2_665 ? B6 B5 B3 60.14(9) . 2_665 ? C8A B5 B2 121.55(13) . 2_665 ? B4 B5 B2 60.03(9) . 2_665 ? B6 B5 B2 108.38(11) . 2_665 ? B3 B5 B2 60.21(9) 2_665 2_665 ? C8A B5 B1 121.06(14) . . ? B4 B5 B1 60.23(9) . . ? B6 B5 B1 60.05(9) . . ? B3 B5 B1 108.48(11) 2_665 . ? B2 B5 B1 108.67(11) 2_665 . ? B6 C9 H9A 109.5 . . ? B6 C9 H9B 109.5 . . ? H9A C9 H9B 109.5 . . ? B6 C9 H9C 109.5 . . ? H9A C9 H9C 109.5 . . ? H9B C9 H9C 109.5 . . ? C12 O1 C11 114.48(17) . . ? C11 C10 H10A 109.5 . . ? C11 C10 H10B 109.5 . . ? H10A C10 H10B 109.5 . . ? C11 C10 H10C 109.5 . . ? H10A C10 H10C 109.5 . . ? H10B C10 H10C 109.5 . . ? O1 C11 C10 111.76(16) . . ? O1 C11 H11A 109.3 . . ? C10 C11 H11A 109.3 . . ? O1 C11 H11B 109.3 . . ? C10 C11 H11B 109.3 . . ? H11A C11 H11B 107.9 . . ? O1 C12 C13 110.62(19) . . ? O1 C12 H12A 109.5 . . ? C13 C12 H12A 109.5 . . ? O1 C12 H12B 109.5 . . ? C13 C12 H12B 109.5 . . ? H12A C12 H12B 108.1 . . ? C12 C13 H13A 109.5 . . ? C12 C13 H13B 109.5 . . ? H13A C13 H13B 109.5 . . ? C12 C13 H13C 109.5 . . ? H13A C13 H13C 109.5 . . ? H13B C13 H13C 109.5 . . ? C16 O2 C15 112.4(4) . . ? O2 C15 C14 109.4(4) . . ? O2 C15 H15A 109.8 . . ? C14 C15 H15A 109.8 . . ? O2 C15 H15B 109.8 . . ? C14 C15 H15B 109.8 . . ? H15A C15 H15B 108.2 . . ? O2 C16 C17 109.1(6) . . ? O2 C16 H16A 109.9 . . ? C17 C16 H16A 109.9 . . ? O2 C16 H16B 109.9 . . ? C17 C16 H16B 109.9 . . ? H16A C16 H16B 108.3 . . ? C21 O3 C20 111.2(7) . . ? C20 C19 H19A 109.5 . . ? C20 C19 H19B 109.5 . . ? H19A C19 H19B 109.5 . . ? C20 C19 H19C 109.5 . . ? H19A C19 H19C 109.5 . . ? H19B C19 H19C 109.5 . . ? O3 C20 C19 108.5(6) . . ? O3 C20 H20A 110.0 . . ? C19 C20 H20A 110.0 . . ? O3 C20 H20B 110.0 . . ? C19 C20 H20B 110.0 . . ? H20A C20 H20B 108.4 . . ? O3 C21 C22 107.5(8) . . ? O3 C21 H21A 110.2 . . ? C22 C21 H21A 110.2 . . ? O3 C21 H21B 110.2 . . ? C22 C21 H21B 110.2 . . ? H21A C21 H21B 108.5 . . ? C21 C22 H22A 109.5 . . ? C21 C22 H22B 109.5 . . ? H22A C22 H22B 109.5 . . ? C21 C22 H22C 109.5 . . ? H22A C22 H22C 109.5 . . ? H22B C22 H22C 109.5 . . ? _diffrn_measured_fraction_theta_max 0.982 _diffrn_reflns_theta_full 30.06 _diffrn_measured_fraction_theta_full 0.982 _refine_diff_density_max 0.382 _refine_diff_density_min -0.294 _refine_diff_density_rms 0.061 # Attachment 'TTF-CB.cif' data_ros5 _database_code_depnum_ccdc_archive 'CCDC 611972' _audit_creation_method SHELXL-97 _chemical_name_systematic ; Tetrathiafulvalenium Dodecamethylcarba-closo-dodecaboranate ; _chemical_name_common 'TTf+ Car-' _chemical_melting_point ? _chemical_formula_moiety 'C13 H36 B11, C6 H4 S4' _chemical_formula_sum 'C19 H40 B11 S4' _chemical_formula_weight 515.66 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' B B 0.0013 0.0007 '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 _symmetry_space_group_name_Hall '-P 2yn' 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 9.1393(8) _cell_length_b 13.3909(13) _cell_length_c 12.5744(10) _cell_angle_alpha 90.00 _cell_angle_beta 109.609(5) _cell_angle_gamma 90.00 _cell_volume 1449.6(2) _cell_formula_units_Z 2 _cell_measurement_temperature 173(2) _cell_measurement_reflns_used 527 _cell_measurement_theta_min 2.30 _cell_measurement_theta_max 28.03 _exptl_crystal_description plate _exptl_crystal_colour black _exptl_crystal_size_max 0.3 _exptl_crystal_size_mid 0.3 _exptl_crystal_size_min 0.1 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.181 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 546 _exptl_absorpt_coefficient_mu 0.337 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details 'Semi-empirical (SADABS procedure)' _exptl_absorpt_correction_T_min 0.928 _exptl_absorpt_correction_T_max 0.999 _exptl_special_details ; ? ; _diffrn_ambient_temperature 173(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 SMART' _diffrn_measurement_method ; \w-scan, frame range 0.3 deg, hemisphere ; _diffrn_standards_number none _diffrn_standards_interval_count 0 _diffrn_standards_interval_time 0 _diffrn_standards_decay_% 0 _diffrn_reflns_number 13301 _diffrn_reflns_av_R_equivalents 0.0282 _diffrn_reflns_av_sigmaI/netI 0.0262 _diffrn_reflns_limit_h_min -12 _diffrn_reflns_limit_h_max 12 _diffrn_reflns_limit_k_min -12 _diffrn_reflns_limit_k_max 19 _diffrn_reflns_limit_l_min -17 _diffrn_reflns_limit_l_max 17 _diffrn_reflns_theta_min 2.30 _diffrn_reflns_theta_max 30.52 _reflns_number_total 4128 _reflns_number_gt 3505 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'SMART V5.630 (BrukerAXS, 1997-2001)' _computing_cell_refinement 'SAINT V6.28 (BrukerAXS, 1997-2001)' _computing_data_reduction 'SAINT & SADABS V2.06 (Sheldrick, 2000)' _computing_structure_solution 'SHELXTL v. 6.12 (Sheldrick, 2001)' _computing_structure_refinement 'SHELXTL v. 6.12 (Sheldrick, 2001)' _computing_molecular_graphics 'XP V5.06 (BrukerAXS, 1997-99)' _computing_publication_material 'SHELXL-93, XCIF V5.05 (BrukerAXS, 1997-99)' _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. 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 _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0771P)^2^+0.1363P] 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 4128 _refine_ls_number_parameters 158 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0514 _refine_ls_R_factor_gt 0.0454 _refine_ls_wR_factor_ref 0.1319 _refine_ls_wR_factor_gt 0.1292 _refine_ls_goodness_of_fit_ref 1.109 _refine_ls_restrained_S_all 1.109 _refine_ls_shift/su_max 0.008 _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 S1 S 0.17111(5) 0.11891(3) 0.53780(3) 0.03760(13) Uani 1 1 d . . . S2 S 0.20203(5) -0.09583(3) 0.56770(3) 0.03478(13) Uani 1 1 d . . . C21 C 0.08062(17) 0.00500(10) 0.52306(11) 0.0267(3) Uani 1 1 d . . . C22 C 0.3705(2) -0.02658(14) 0.61058(14) 0.0426(4) Uani 1 1 d . . . H22A H 0.4693 -0.0574 0.6420 0.051 Uiso 1 1 calc R . . C23 C 0.35641(19) 0.07192(14) 0.59778(15) 0.0433(4) Uani 1 1 d . . . H23A H 0.4446 0.1146 0.6207 0.052 Uiso 1 1 calc R . . B1 B 0.98893(17) 0.12213(12) 0.96341(12) 0.0249(3) Uani 1 1 d . . . C2 C 1.09956(17) 0.03460(12) 0.91727(12) 0.0287(3) Uani 0.50 1 d P . . B2 B 1.09956(17) 0.03460(12) 0.91727(12) 0.0287(3) Uani 0.50 1 d P . . B3 B 1.16045(17) 0.06972(12) 1.06109(12) 0.0257(3) Uani 1 1 d . . . B4 B 0.99150(18) 0.08340(12) 1.09920(12) 0.0257(3) Uani 1 1 d . . . B5 B 0.82738(16) 0.05691(12) 0.97761(12) 0.0261(3) Uani 1 1 d . . . B6 B 0.89523(17) 0.02736(12) 0.86398(12) 0.0255(3) Uani 1 1 d . . . C11 C 0.98132(19) 0.23675(11) 0.92719(13) 0.0369(3) Uani 1 1 d . . . H11A H 0.8782 0.2516 0.8731 0.055 Uiso 0.567(19) 1 calc PR . . H11B H 1.0603 0.2499 0.8921 0.055 Uiso 0.567(19) 1 calc PR . . H11C H 1.0008 0.2791 0.9941 0.055 Uiso 0.567(19) 1 calc PR . . H11D H 1.0813 0.2688 0.9664 0.055 Uiso 0.433(19) 1 calc PR . . H11E H 0.8992 0.2705 0.9474 0.055 Uiso 0.433(19) 1 calc PR . . H11F H 0.9587 0.2413 0.8455 0.055 Uiso 0.433(19) 1 calc PR . . C12 C 1.1964(2) 0.06790(14) 0.83957(14) 0.0426(4) Uani 1 1 d . . . H12A H 1.2492 0.0112 0.8229 0.064 Uiso 1 1 d R . . H12B H 1.2711 0.1176 0.8780 0.064 Uiso 1 1 d R . . H12C H 1.1269 0.0953 0.7705 0.064 Uiso 1 1 d R . . C13 C 1.31213(19) 0.13596(14) 1.11622(14) 0.0402(4) Uani 1 1 d . . . H13A H 1.3941 0.0946 1.1676 0.060 Uiso 0.50(2) 1 calc PR . . H13B H 1.2877 0.1913 1.1584 0.060 Uiso 0.50(2) 1 calc PR . . H13C H 1.3477 0.1626 1.0565 0.060 Uiso 0.50(2) 1 calc PR . . H13D H 1.2923 0.2044 1.0874 0.060 Uiso 0.50(2) 1 calc PR . . H13E H 1.3987 0.1077 1.0966 0.060 Uiso 0.50(2) 1 calc PR . . H13F H 1.3387 0.1364 1.1985 0.060 Uiso 0.50(2) 1 calc PR . . C14 C 0.9835(2) 0.16080(13) 1.19409(13) 0.0399(4) Uani 1 1 d . . . H14A H 1.0852 0.1644 1.2537 0.060 Uiso 0.15(2) 1 calc PR . . H14B H 0.9054 0.1384 1.2265 0.060 Uiso 0.15(2) 1 calc PR . . H14C H 0.9549 0.2270 1.1602 0.060 Uiso 0.15(2) 1 calc PR . . H14D H 0.8785 0.1887 1.1732 0.060 Uiso 0.85(2) 1 calc PR . . H14E H 1.0583 0.2148 1.2004 0.060 Uiso 0.85(2) 1 calc PR . . H14F H 1.0088 0.1262 1.2667 0.060 Uiso 0.85(2) 1 calc PR . . C15 C 0.66335(19) 0.10862(13) 0.95660(15) 0.0421(4) Uani 1 1 d . . . H15A H 0.5890 0.0843 0.8854 0.063 Uiso 0.38(2) 1 calc PR . . H15B H 0.6743 0.1812 0.9526 0.063 Uiso 0.38(2) 1 calc PR . . H15C H 0.6257 0.0922 1.0189 0.063 Uiso 0.38(2) 1 calc PR . . H15D H 0.6704 0.1541 1.0191 0.063 Uiso 0.62(2) 1 calc PR . . H15E H 0.5850 0.0573 0.9520 0.063 Uiso 0.62(2) 1 calc PR . . H15F H 0.6336 0.1463 0.8857 0.063 Uiso 0.62(2) 1 calc PR . . C16 C 0.79749(19) 0.05468(14) 0.73560(12) 0.0392(4) Uani 1 1 d . . . H16A H 0.7548 -0.0065 0.6941 0.059 Uiso 1 1 calc R . . H16B H 0.8656 0.0874 0.7004 0.059 Uiso 1 1 calc R . . H16C H 0.7123 0.0999 0.7339 0.059 Uiso 1 1 calc 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 S1 0.0399(2) 0.0306(2) 0.0386(2) 0.00214(15) 0.00823(17) -0.00627(15) S2 0.0349(2) 0.0318(2) 0.0354(2) 0.00098(14) 0.00874(16) 0.00546(14) C21 0.0323(7) 0.0255(6) 0.0226(6) 0.0006(5) 0.0094(5) -0.0002(5) C22 0.0294(7) 0.0562(11) 0.0385(8) -0.0011(8) 0.0065(6) 0.0024(7) C23 0.0322(8) 0.0514(10) 0.0422(9) -0.0023(7) 0.0072(7) -0.0102(7) B1 0.0246(7) 0.0283(7) 0.0200(6) -0.0006(5) 0.0052(5) -0.0016(5) C2 0.0266(7) 0.0360(8) 0.0224(6) -0.0019(6) 0.0066(5) -0.0013(6) B2 0.0266(7) 0.0360(8) 0.0224(6) -0.0019(6) 0.0066(5) -0.0013(6) B3 0.0232(6) 0.0313(8) 0.0201(6) -0.0005(5) 0.0040(5) -0.0027(6) B4 0.0277(7) 0.0300(8) 0.0189(6) -0.0027(5) 0.0070(5) -0.0015(6) B5 0.0215(6) 0.0325(8) 0.0234(7) -0.0004(6) 0.0062(5) -0.0006(6) B6 0.0242(7) 0.0313(8) 0.0188(6) -0.0002(5) 0.0044(5) -0.0028(6) C11 0.0430(8) 0.0326(8) 0.0329(7) 0.0030(6) 0.0099(6) -0.0018(6) C12 0.0410(9) 0.0541(11) 0.0356(8) -0.0032(7) 0.0168(7) -0.0042(8) C13 0.0332(8) 0.0460(9) 0.0346(8) -0.0009(7) 0.0023(6) -0.0100(7) C14 0.0525(10) 0.0390(9) 0.0301(7) -0.0075(6) 0.0163(7) -0.0011(7) C15 0.0300(8) 0.0467(10) 0.0485(10) 0.0024(7) 0.0116(7) 0.0052(7) C16 0.0420(8) 0.0455(9) 0.0220(7) 0.0038(6) 0.0001(6) -0.0036(7) _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 C21 1.7154(14) . ? S1 C23 1.7249(18) . ? S2 C21 1.7180(14) . ? S2 C22 1.7218(18) . ? C21 C21 1.397(3) 3_556 ? C22 C23 1.330(3) . ? C22 H22A 0.9500 . ? C23 H23A 0.9500 . ? B1 C11 1.596(2) . ? B1 C2 1.768(2) . ? B1 B5 1.775(2) . ? B1 B4 1.777(2) . ? B1 B3 1.779(2) . ? B1 B6 1.786(2) . ? C2 C12 1.587(2) . ? C2 B5 1.761(2) 3_757 ? C2 B6 1.762(2) . ? C2 B4 1.765(2) 3_757 ? C2 B3 1.768(2) . ? B3 C13 1.595(2) . ? B3 B4 1.773(2) . ? B3 B6 1.777(2) 3_757 ? B3 B5 1.778(2) 3_757 ? B4 C14 1.600(2) . ? B4 B2 1.765(2) 3_757 ? B4 C2 1.765(2) 3_757 ? B4 B6 1.779(2) 3_757 ? B4 B5 1.782(2) . ? B5 C15 1.591(2) . ? B5 B2 1.761(2) 3_757 ? B5 C2 1.761(2) 3_757 ? B5 B3 1.778(2) 3_757 ? B5 B6 1.782(2) . ? B6 C16 1.603(2) . ? B6 B3 1.777(2) 3_757 ? B6 B4 1.779(2) 3_757 ? C11 H11A 0.9800 . ? C11 H11B 0.9800 . ? C11 H11C 0.9800 . ? C11 H11D 0.9800 . ? C11 H11E 0.9800 . ? C11 H11F 0.9800 . ? C12 H12A 0.9600 . ? C12 H12B 0.9600 . ? C12 H12C 0.9600 . ? C13 H13A 0.9800 . ? C13 H13B 0.9800 . ? C13 H13C 0.9800 . ? C13 H13D 0.9800 . ? C13 H13E 0.9800 . ? C13 H13F 0.9800 . ? C14 H14A 0.9800 . ? C14 H14B 0.9800 . ? C14 H14C 0.9800 . ? C14 H14D 0.9800 . ? C14 H14E 0.9800 . ? C14 H14F 0.9800 . ? C15 H15A 0.9800 . ? C15 H15B 0.9800 . ? C15 H15C 0.9800 . ? C15 H15D 0.9800 . ? C15 H15E 0.9800 . ? C15 H15F 0.9800 . ? C16 H16A 0.9800 . ? C16 H16B 0.9800 . ? C16 H16C 0.9800 . ? 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 C21 S1 C23 95.15(8) . . ? C21 S2 C22 95.20(8) . . ? C21 C21 S1 122.22(14) 3_556 . ? C21 C21 S2 122.41(14) 3_556 . ? S1 C21 S2 115.37(8) . . ? C23 C22 S2 117.14(13) . . ? C23 C22 H22A 121.4 . . ? S2 C22 H22A 121.4 . . ? C22 C23 S1 117.12(13) . . ? C22 C23 H23A 121.4 . . ? S1 C23 H23A 121.4 . . ? C11 B1 C2 121.25(12) . . ? C11 B1 B5 122.94(12) . . ? C2 B1 B5 107.06(11) . . ? C11 B1 B4 122.69(12) . . ? C2 B1 B4 107.29(11) . . ? B5 B1 B4 60.20(8) . . ? C11 B1 B3 121.35(12) . . ? C2 B1 B3 59.78(8) . . ? B5 B1 B3 107.84(11) . . ? B4 B1 B3 59.81(8) . . ? C11 B1 B6 121.27(12) . . ? C2 B1 B6 59.46(8) . . ? B5 B1 B6 60.08(8) . . ? B4 B1 B6 108.30(11) . . ? B3 B1 B6 107.90(11) . . ? C12 C2 B5 120.56(12) . 3_757 ? C12 C2 B6 121.35(12) . . ? B5 C2 B6 109.48(10) 3_757 . ? C12 C2 B4 121.18(12) . 3_757 ? B5 C2 B4 60.68(9) 3_757 3_757 ? B6 C2 B4 60.56(9) . 3_757 ? C12 C2 B3 120.40(12) . . ? B5 C2 B3 60.49(9) 3_757 . ? B6 C2 B3 109.46(10) . . ? B4 C2 B3 109.41(10) 3_757 . ? C12 C2 B1 120.96(13) . . ? B5 C2 B1 109.24(10) 3_757 . ? B6 C2 B1 60.76(8) . . ? B4 C2 B1 109.44(10) 3_757 . ? B3 C2 B1 60.43(8) . . ? C13 B3 C2 121.45(11) . . ? C13 B3 B4 122.26(12) . . ? C2 B3 B4 107.47(10) . . ? C13 B3 B6 122.56(11) . 3_757 ? C2 B3 B6 107.45(11) . 3_757 ? B4 B3 B6 60.14(9) . 3_757 ? C13 B3 B5 121.62(12) . 3_757 ? C2 B3 B5 59.57(9) . 3_757 ? B4 B3 B5 108.22(11) . 3_757 ? B6 B3 B5 60.18(9) 3_757 3_757 ? C13 B3 B1 121.10(13) . . ? C2 B3 B1 59.79(8) . . ? B4 B3 B1 60.03(8) . . ? B6 B3 B1 108.17(10) 3_757 . ? B5 B3 B1 107.99(10) 3_757 . ? C14 B4 B2 121.97(11) . 3_757 ? C14 B4 C2 121.97(11) . 3_757 ? C14 B4 B3 122.02(12) . . ? B2 B4 B3 107.14(11) 3_757 . ? C2 B4 B3 107.14(11) 3_757 . ? C14 B4 B1 122.56(12) . . ? B2 B4 B1 107.14(10) 3_757 . ? C2 B4 B1 107.14(10) 3_757 . ? B3 B4 B1 60.16(8) . . ? C14 B4 B6 120.94(12) . 3_757 ? B2 B4 B6 59.63(8) 3_757 3_757 ? C2 B4 B6 59.63(8) 3_757 3_757 ? B3 B4 B6 60.04(9) . 3_757 ? B1 B4 B6 108.19(10) . 3_757 ? C14 B4 B5 122.19(12) . . ? B2 B4 B5 59.54(9) 3_757 . ? C2 B4 B5 59.54(9) 3_757 . ? B3 B4 B5 107.83(10) . . ? B1 B4 B5 59.85(8) . . ? B6 B4 B5 107.82(11) 3_757 . ? C15 B5 B2 121.75(12) . 3_757 ? C15 B5 C2 121.75(12) . 3_757 ? C15 B5 B1 122.57(13) . . ? B2 B5 B1 107.41(10) 3_757 . ? C2 B5 B1 107.41(10) 3_757 . ? C15 B5 B3 120.78(12) . 3_757 ? B2 B5 B3 59.94(9) 3_757 3_757 ? C2 B5 B3 59.94(9) 3_757 3_757 ? B1 B5 B3 108.13(10) . 3_757 ? C15 B5 B4 122.06(12) . . ? B2 B5 B4 59.77(9) 3_757 . ? C2 B5 B4 59.77(9) 3_757 . ? B1 B5 B4 59.95(8) . . ? B3 B5 B4 108.23(11) 3_757 . ? C15 B5 B6 121.70(12) . . ? B2 B5 B6 107.51(11) 3_757 . ? C2 B5 B6 107.51(11) 3_757 . ? B1 B5 B6 60.25(8) . . ? B3 B5 B6 59.89(8) 3_757 . ? B4 B5 B6 108.24(10) . . ? C16 B6 C2 122.11(11) . . ? C16 B6 B3 122.61(12) . 3_757 ? C2 B6 B3 107.10(11) . 3_757 ? C16 B6 B4 122.09(12) . 3_757 ? C2 B6 B4 59.81(9) . 3_757 ? B3 B6 B4 59.82(9) 3_757 3_757 ? C16 B6 B5 122.03(12) . . ? C2 B6 B5 107.00(10) . . ? B3 B6 B5 59.93(9) 3_757 . ? B4 B6 B5 107.77(10) 3_757 . ? C16 B6 B1 121.14(13) . . ? C2 B6 B1 59.78(8) . . ? B3 B6 B1 107.70(10) 3_757 . ? B4 B6 B1 108.06(10) 3_757 . ? B5 B6 B1 59.67(8) . . ? B1 C11 H11A 109.5 . . ? B1 C11 H11B 109.5 . . ? H11A C11 H11B 109.5 . . ? B1 C11 H11C 109.5 . . ? H11A C11 H11C 109.5 . . ? H11B C11 H11C 109.5 . . ? B1 C11 H11D 109.5 . . ? H11A C11 H11D 141.1 . . ? H11B C11 H11D 56.3 . . ? H11C C11 H11D 56.3 . . ? B1 C11 H11E 109.5 . . ? H11A C11 H11E 56.3 . . ? H11B C11 H11E 141.1 . . ? H11C C11 H11E 56.3 . . ? H11D C11 H11E 109.5 . . ? B1 C11 H11F 109.5 . . ? H11A C11 H11F 56.3 . . ? H11B C11 H11F 56.3 . . ? H11C C11 H11F 141.1 . . ? H11D C11 H11F 109.5 . . ? H11E C11 H11F 109.5 . . ? C2 C12 H12A 109.7 . . ? C2 C12 H12B 109.5 . . ? H12A C12 H12B 109.5 . . ? C2 C12 H12C 109.1 . . ? H12A C12 H12C 109.5 . . ? H12B C12 H12C 109.5 . . ? B3 C13 H13A 109.5 . . ? B3 C13 H13B 109.5 . . ? H13A C13 H13B 109.5 . . ? B3 C13 H13C 109.5 . . ? H13A C13 H13C 109.5 . . ? H13B C13 H13C 109.5 . . ? B3 C13 H13D 109.5 . . ? H13A C13 H13D 141.1 . . ? H13B C13 H13D 56.3 . . ? H13C C13 H13D 56.3 . . ? B3 C13 H13E 109.5 . . ? H13A C13 H13E 56.3 . . ? H13B C13 H13E 141.1 . . ? H13C C13 H13E 56.3 . . ? H13D C13 H13E 109.5 . . ? B3 C13 H13F 109.5 . . ? H13A C13 H13F 56.3 . . ? H13B C13 H13F 56.3 . . ? H13C C13 H13F 141.1 . . ? H13D C13 H13F 109.5 . . ? H13E C13 H13F 109.5 . . ? B4 C14 H14A 109.5 . . ? B4 C14 H14B 109.5 . . ? H14A C14 H14B 109.5 . . ? B4 C14 H14C 109.5 . . ? H14A C14 H14C 109.5 . . ? H14B C14 H14C 109.5 . . ? B4 C14 H14D 109.5 . . ? H14A C14 H14D 141.1 . . ? H14B C14 H14D 56.3 . . ? H14C C14 H14D 56.3 . . ? B4 C14 H14E 109.5 . . ? H14A C14 H14E 56.3 . . ? H14B C14 H14E 141.1 . . ? H14C C14 H14E 56.3 . . ? H14D C14 H14E 109.5 . . ? B4 C14 H14F 109.5 . . ? H14A C14 H14F 56.3 . . ? H14B C14 H14F 56.3 . . ? H14C C14 H14F 141.1 . . ? H14D C14 H14F 109.5 . . ? H14E C14 H14F 109.5 . . ? B5 C15 H15A 109.5 . . ? B5 C15 H15B 109.5 . . ? H15A C15 H15B 109.5 . . ? B5 C15 H15C 109.5 . . ? H15A C15 H15C 109.5 . . ? H15B C15 H15C 109.5 . . ? B5 C15 H15D 109.5 . . ? H15A C15 H15D 141.1 . . ? H15B C15 H15D 56.3 . . ? H15C C15 H15D 56.3 . . ? B5 C15 H15E 109.5 . . ? H15A C15 H15E 56.3 . . ? H15B C15 H15E 141.1 . . ? H15C C15 H15E 56.3 . . ? H15D C15 H15E 109.5 . . ? B5 C15 H15F 109.5 . . ? H15A C15 H15F 56.3 . . ? H15B C15 H15F 56.3 . . ? H15C C15 H15F 141.1 . . ? H15D C15 H15F 109.5 . . ? H15E C15 H15F 109.5 . . ? B6 C16 H16A 109.5 . . ? B6 C16 H16B 109.5 . . ? H16A C16 H16B 109.5 . . ? B6 C16 H16C 109.5 . . ? H16A C16 H16C 109.5 . . ? H16B C16 H16C 109.5 . . ? _diffrn_measured_fraction_theta_max 0.933 _diffrn_reflns_theta_full 29.00 _diffrn_measured_fraction_theta_full 0.999 _refine_diff_density_max 0.500 _refine_diff_density_min -0.230 _refine_diff_density_rms 0.072