# Supplementary Material (ESI) for Chemical Communications # This journal is © The Royal Society of Chemistry 2003 data_global _audit_creation_method 'SHELXL-97 plus manual editing' _journal_coden_Cambridge 182 loop_ _publ_author_name 'Jeremy M. Rawson' 'Andrew D. Bond' 'Caroline S. Clarke' 'Delia A. Haynes' _publ_contact_author_name 'Jeremy M. Rawson' _publ_contact_author_address ; University of Cambridge Department of Chemistry Lensfield Road Cambridge CB2 1EW U.K. ; _publ_contact_author_email jmr31@cus.cam.ac.uk _publ_requested_journal 'Chemical Communications' _publ_section_title ; Small molecule fixation by a dithiadiazolyl radical: X-ray ctrystal structures of (CF3C6H3FCNSSN)2 and (CF3C6H3FCNSSN)2.G (G = N2, Ar, CO2 and SO2) ; ################################# ## Structure denoted 1 in text ## ################################# data_jr0037 _database_code_CSD 214198 _chemical_name_systematic ? _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C8 H3 F4 N2 S2' _chemical_formula_sum 'C8 H3 F4 N2 S2' _chemical_formula_weight 267.24 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' F F 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' S S 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting triclinic _symmetry_space_group_name_H-M P-1 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 10.6611(6) _cell_length_b 11.6471(5) _cell_length_c 16.0947(5) _cell_angle_alpha 75.318(3) _cell_angle_beta 79.351(3) _cell_angle_gamma 89.511(2) _cell_volume 1898.40(15) _cell_formula_units_Z 8 _cell_measurement_temperature 180(2) _cell_measurement_reflns_used 9506 _cell_measurement_theta_min 1.00 _cell_measurement_theta_max 24.71 _exptl_crystal_description block _exptl_crystal_colour red _exptl_crystal_size_max 0.35 _exptl_crystal_size_mid 0.12 _exptl_crystal_size_min 0.12 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.870 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1064 _exptl_absorpt_coefficient_mu 0.591 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.859 _exptl_absorpt_correction_T_max 0.932 _exptl_absorpt_process_details 'Sortav Blessing (1995)' _exptl_special_details ; ? ; _diffrn_ambient_temperature 180(2) _diffrn_radiation_wavelength 0.7107 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Nonius KappaCCD' _diffrn_measurement_method 'thin-slice \w and \f scans' _diffrn_standards_number 0 _diffrn_reflns_number 15483 _diffrn_reflns_av_R_equivalents 0.0494 _diffrn_reflns_av_sigmaI/netI 0.0598 _diffrn_reflns_limit_h_min 0 _diffrn_reflns_limit_h_max 12 _diffrn_reflns_limit_k_min -13 _diffrn_reflns_limit_k_max 13 _diffrn_reflns_limit_l_min -18 _diffrn_reflns_limit_l_max 18 _diffrn_reflns_theta_min 1.33 _diffrn_reflns_theta_max 24.67 _diffrn_measured_fraction_theta_max 0.996 _diffrn_reflns_theta_full 24.67 _diffrn_measured_fraction_theta_full 0.996 _reflns_number_total 6425 _reflns_number_gt 4717 _reflns_threshold_expression I>2\s(I) _computing_data_collection 'Collect (Nonius, 1998)' _computing_cell_refinement 'HKL Scalepack (Otwinowski & Minor, 1997)' _computing_data_reduction ; HKL Denzo and Scalepack (Otwinowski & Minor, 1997) ; _computing_structure_solution 'SIR-92 (Altomare et al., 1994)' _computing_structure_refinement 'SHELXTL v6.12 (Bruker AXS, 2001)' _computing_publication_material 'SHELXTL v6.12 (Bruker AXS, 2001)' _computing_molecular_graphics 'SHELXTL v6.12 (Bruker AXS, 2001)' _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^)+(0.1042P)^2^+0.1127P] 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 6425 _refine_ls_number_parameters 578 _refine_ls_number_restraints 24 _refine_ls_R_factor_all 0.0712 _refine_ls_R_factor_gt 0.0471 _refine_ls_wR_factor_ref 0.1626 _refine_ls_wR_factor_gt 0.1295 _refine_ls_goodness_of_fit_ref 1.046 _refine_ls_restrained_S_all 1.046 _refine_ls_shift/su_max 0.009 _refine_ls_shift/su_mean 0.001 _refine_diff_density_max 0.976 _refine_diff_density_min -0.566 _refine_diff_density_rms 0.164 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 F11 F 0.6026(3) 0.7195(2) 0.16520(16) 0.0495(7) Uani 1 1 d . . . F12 F 0.4064(4) 0.5635(2) 0.14797(16) 0.0745(10) Uani 1 1 d D . . F13 F 0.5397(3) 0.6281(2) 0.02935(18) 0.0607(8) Uani 1 1 d D . . F14 F 0.3423(3) 0.6374(2) 0.02890(18) 0.0621(8) Uani 1 1 d D . . S11 S 0.51511(10) 1.27874(8) 0.19317(6) 0.0309(3) Uani 1 1 d . . . S12 S 0.32632(10) 1.29466(8) 0.17325(6) 0.0310(3) Uani 1 1 d . . . N11 N 0.5287(3) 1.1459(3) 0.17655(19) 0.0285(7) Uani 1 1 d . . . N12 N 0.3172(3) 1.1654(3) 0.15263(19) 0.0304(8) Uani 1 1 d . . . C10 C 0.4247(4) 1.1051(3) 0.1560(2) 0.0269(8) Uani 1 1 d . . . C11 C 0.4284(4) 0.9893(3) 0.1342(2) 0.0255(8) Uani 1 1 d . . . C12 C 0.5187(4) 0.9066(3) 0.1602(2) 0.0286(9) Uani 1 1 d . . . H12 H 0.5801 0.9244 0.1916 0.034 Uiso 1 1 calc R . . C13 C 0.5170(4) 0.7999(3) 0.1397(2) 0.0291(9) Uani 1 1 d . . . C14 C 0.4299(4) 0.7692(3) 0.0935(2) 0.0280(9) Uani 1 1 d . . . C15 C 0.3425(4) 0.8521(3) 0.0665(2) 0.0313(9) Uani 1 1 d . . . H15 H 0.2836 0.8345 0.0334 0.038 Uiso 1 1 calc R . . C16 C 0.3400(4) 0.9607(3) 0.0872(2) 0.0313(9) Uani 1 1 d . . . H16 H 0.2780 1.0161 0.0695 0.038 Uiso 1 1 calc R . . C17 C 0.4302(4) 0.6496(3) 0.0755(2) 0.0360(10) Uani 1 1 d D . . F21 F 0.4838(3) 0.61764(19) 0.44481(14) 0.0459(6) Uani 1 1 d . . . F22 F 0.2906(3) 0.44855(19) 0.44041(15) 0.0614(8) Uani 1 1 d D . . F23 F 0.4313(2) 0.48891(19) 0.32358(15) 0.0440(6) Uani 1 1 d D . . F24 F 0.2341(2) 0.4965(2) 0.31571(16) 0.0482(7) Uani 1 1 d D . . S21 S 0.41394(10) 1.19734(8) 0.39137(6) 0.0283(3) Uani 1 1 d . . . S22 S 0.22632(9) 1.20826(8) 0.36954(6) 0.0291(3) Uani 1 1 d . . . N21 N 0.4259(3) 1.0581(3) 0.38843(18) 0.0263(7) Uani 1 1 d . . . N22 N 0.2152(3) 1.0710(3) 0.36260(19) 0.0271(7) Uani 1 1 d . . . C20 C 0.3211(4) 1.0100(3) 0.3744(2) 0.0231(8) Uani 1 1 d . . . C21 C 0.3206(3) 0.8851(3) 0.3706(2) 0.0229(8) Uani 1 1 d . . . C22 C 0.4059(4) 0.8083(3) 0.4099(2) 0.0261(8) Uani 1 1 d . . . H22 H 0.4646 0.8358 0.4390 0.031 Uiso 1 1 calc R . . C23 C 0.4034(4) 0.6920(3) 0.4057(2) 0.0264(8) Uani 1 1 d . . . C24 C 0.3196(4) 0.6491(3) 0.3627(2) 0.0255(8) Uani 1 1 d . . . C25 C 0.2369(4) 0.7267(3) 0.3229(2) 0.0269(8) Uani 1 1 d . . . H25 H 0.1806 0.6997 0.2919 0.032 Uiso 1 1 calc R . . C26 C 0.2353(4) 0.8433(3) 0.3280(2) 0.0266(8) Uani 1 1 d . . . H26 H 0.1757 0.8952 0.3024 0.032 Uiso 1 1 calc R . . C27 C 0.3195(4) 0.5211(3) 0.3610(2) 0.0315(9) Uani 1 1 d D . . F31 F 0.0031(2) 0.41706(18) 0.57854(13) 0.0388(6) Uani 1 1 d . . . F32 F 0.2016(3) 0.24632(19) 0.57571(14) 0.0552(8) Uani 1 1 d D . . F33 F 0.0712(2) 0.21507(19) 0.69735(14) 0.0439(6) Uani 1 1 d D . . F34 F 0.2721(3) 0.21796(19) 0.69506(16) 0.0492(7) Uani 1 1 d D . . S31 S 0.08868(10) 0.97670(8) 0.59289(6) 0.0288(3) Uani 1 1 d . . . S32 S 0.27652(9) 0.97352(8) 0.61365(6) 0.0287(3) Uani 1 1 d . . . N31 N 0.0780(3) 0.8351(3) 0.59816(19) 0.0285(7) Uani 1 1 d . . . N32 N 0.2891(3) 0.8308(3) 0.62326(19) 0.0268(7) Uani 1 1 d . . . C30 C 0.1836(4) 0.7775(3) 0.6142(2) 0.0236(8) Uani 1 1 d . . . C31 C 0.1841(3) 0.6480(3) 0.6239(2) 0.0226(8) Uani 1 1 d . . . C32 C 0.0902(4) 0.5927(3) 0.5958(2) 0.0250(8) Uani 1 1 d . . . H32 H 0.0265 0.6378 0.5697 0.030 Uiso 1 1 calc R . . C33 C 0.0917(4) 0.4723(3) 0.6064(2) 0.0262(8) Uani 1 1 d . . . C34 C 0.1825(4) 0.4022(3) 0.6456(2) 0.0251(8) Uani 1 1 d . . . C35 C 0.2739(4) 0.4579(3) 0.6740(2) 0.0287(9) Uani 1 1 d . . . H35 H 0.3363 0.4124 0.7015 0.034 Uiso 1 1 calc R . . C36 C 0.2749(4) 0.5798(3) 0.6627(2) 0.0265(8) Uani 1 1 d . . . H36 H 0.3390 0.6173 0.6819 0.032 Uiso 1 1 calc R . . C37 C 0.1804(4) 0.2714(3) 0.6530(2) 0.0340(10) Uani 1 1 d D . . F41 F -0.0984(2) 0.3407(2) 0.83404(15) 0.0464(6) Uani 1 1 d . . . F42 F 0.0936(4) 0.1641(2) 0.87028(17) 0.0910(13) Uani 1 1 d D . . F43 F -0.0454(3) 0.1641(2) 0.98335(19) 0.0677(8) Uani 1 1 d D . . F44 F 0.1477(3) 0.1687(2) 0.98856(19) 0.0702(9) Uani 1 1 d D . . S42 S 0.17674(10) 0.92375(8) 0.81178(6) 0.0305(3) Uani 1 1 d . . . S41 S -0.01100(10) 0.92283(8) 0.79027(6) 0.0305(3) Uani 1 1 d . . . N41 N -0.0241(3) 0.7783(3) 0.80891(19) 0.0291(7) Uani 1 1 d . . . N42 N 0.1856(3) 0.7794(3) 0.83478(19) 0.0302(7) Uani 1 1 d . . . C40 C 0.0797(4) 0.7231(3) 0.8313(2) 0.0252(8) Uani 1 1 d . . . C41 C 0.0754(3) 0.5911(3) 0.8577(2) 0.0232(8) Uani 1 1 d . . . C42 C -0.0141(4) 0.5263(3) 0.8327(2) 0.0239(8) Uani 1 1 d . . . H42 H -0.0731 0.5654 0.7985 0.029 Uiso 1 1 calc R . . C43 C -0.0143(4) 0.4041(3) 0.8590(2) 0.0272(9) Uani 1 1 d . . . C44 C 0.0686(4) 0.3428(3) 0.9102(2) 0.0276(9) Uani 1 1 d . . . C45 C 0.1550(4) 0.4090(3) 0.9352(2) 0.0324(9) Uani 1 1 d . . . H45 H 0.2121 0.3695 0.9709 0.039 Uiso 1 1 calc R . . C46 C 0.1598(4) 0.5320(3) 0.9090(2) 0.0307(9) Uani 1 1 d . . . H46 H 0.2207 0.5760 0.9261 0.037 Uiso 1 1 calc R . . C47 C 0.0647(4) 0.2106(3) 0.9359(2) 0.0365(10) Uani 1 1 d 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 F11 0.0617(19) 0.0363(14) 0.0643(15) -0.0225(11) -0.0341(14) 0.0220(13) F12 0.147(3) 0.0239(14) 0.0475(15) -0.0088(11) -0.0050(17) -0.0159(16) F13 0.0590(19) 0.0569(17) 0.0743(18) -0.0410(15) 0.0006(15) 0.0072(14) F14 0.070(2) 0.0560(17) 0.0813(19) -0.0407(15) -0.0349(17) 0.0039(15) S11 0.0270(6) 0.0217(5) 0.0446(6) -0.0112(4) -0.0044(4) -0.0026(4) S12 0.0333(6) 0.0207(5) 0.0412(5) -0.0096(4) -0.0104(4) 0.0063(4) N11 0.0250(19) 0.0228(17) 0.0392(17) -0.0118(13) -0.0048(14) 0.0018(14) N12 0.033(2) 0.0237(17) 0.0387(17) -0.0112(13) -0.0116(15) 0.0046(15) C10 0.026(2) 0.024(2) 0.0293(19) -0.0051(15) -0.0035(16) 0.0002(17) C11 0.025(2) 0.025(2) 0.0250(18) -0.0065(14) 0.0007(16) 0.0006(16) C12 0.030(2) 0.026(2) 0.0319(19) -0.0088(16) -0.0106(17) 0.0007(17) C13 0.031(2) 0.022(2) 0.034(2) -0.0048(15) -0.0096(17) 0.0066(17) C14 0.033(2) 0.027(2) 0.0232(18) -0.0086(15) -0.0010(16) -0.0055(17) C15 0.034(2) 0.030(2) 0.032(2) -0.0091(16) -0.0109(18) -0.0024(18) C16 0.030(2) 0.030(2) 0.035(2) -0.0074(16) -0.0112(18) 0.0071(18) C17 0.043(3) 0.037(2) 0.033(2) -0.0169(18) -0.0066(19) 0.001(2) F21 0.0602(18) 0.0327(13) 0.0517(14) -0.0109(10) -0.0287(13) 0.0190(12) F22 0.106(3) 0.0199(13) 0.0443(14) 0.0020(10) 0.0068(14) -0.0016(13) F23 0.0444(16) 0.0301(13) 0.0598(15) -0.0193(11) -0.0053(12) 0.0121(11) F24 0.0510(17) 0.0263(13) 0.0751(17) -0.0242(11) -0.0159(14) -0.0013(12) S21 0.0298(6) 0.0199(5) 0.0397(5) -0.0129(4) -0.0103(4) 0.0007(4) S22 0.0252(6) 0.0191(5) 0.0453(6) -0.0138(4) -0.0047(4) 0.0017(4) N21 0.0286(19) 0.0191(16) 0.0332(16) -0.0075(12) -0.0099(14) 0.0012(14) N22 0.0268(19) 0.0172(16) 0.0382(17) -0.0100(13) -0.0041(14) -0.0019(13) C20 0.025(2) 0.0209(19) 0.0246(18) -0.0077(14) -0.0045(15) -0.0011(16) C21 0.025(2) 0.0213(19) 0.0218(17) -0.0064(14) -0.0015(15) 0.0011(16) C22 0.029(2) 0.026(2) 0.0261(18) -0.0085(15) -0.0087(16) 0.0020(16) C23 0.034(2) 0.021(2) 0.0244(18) -0.0030(14) -0.0092(16) 0.0078(17) C24 0.030(2) 0.0163(19) 0.0279(19) -0.0046(14) -0.0001(16) -0.0025(16) C25 0.028(2) 0.020(2) 0.0333(19) -0.0068(15) -0.0070(17) -0.0027(16) C26 0.027(2) 0.0184(19) 0.035(2) -0.0041(15) -0.0100(17) 0.0033(16) C27 0.036(3) 0.020(2) 0.037(2) -0.0084(17) -0.0029(19) 0.0022(18) F31 0.0514(16) 0.0270(12) 0.0438(12) -0.0089(9) -0.0232(12) -0.0069(11) F32 0.104(2) 0.0264(13) 0.0345(13) -0.0175(10) 0.0010(13) 0.0020(13) F33 0.0499(17) 0.0255(13) 0.0504(14) -0.0029(10) -0.0038(12) -0.0110(11) F34 0.0553(18) 0.0228(13) 0.0723(16) -0.0096(11) -0.0233(14) 0.0089(12) S31 0.0318(6) 0.0176(5) 0.0387(5) -0.0072(4) -0.0116(4) 0.0040(4) S32 0.0266(6) 0.0174(5) 0.0418(5) -0.0098(4) -0.0025(4) -0.0009(4) N31 0.029(2) 0.0204(17) 0.0399(17) -0.0127(13) -0.0106(15) 0.0052(14) N32 0.0249(19) 0.0166(16) 0.0401(17) -0.0108(13) -0.0037(14) -0.0001(13) C30 0.026(2) 0.0200(19) 0.0254(18) -0.0088(14) -0.0026(16) -0.0015(16) C31 0.024(2) 0.0197(18) 0.0240(17) -0.0075(14) -0.0007(15) -0.0014(16) C32 0.029(2) 0.024(2) 0.0255(18) -0.0084(14) -0.0097(16) 0.0004(16) C33 0.031(2) 0.024(2) 0.0259(18) -0.0114(15) -0.0049(16) -0.0041(17) C34 0.030(2) 0.0199(19) 0.0251(18) -0.0089(14) 0.0002(16) -0.0006(16) C35 0.031(2) 0.023(2) 0.034(2) -0.0093(15) -0.0072(17) 0.0049(17) C36 0.021(2) 0.025(2) 0.037(2) -0.0141(16) -0.0071(17) 0.0007(16) C37 0.045(3) 0.024(2) 0.033(2) -0.0090(16) -0.0066(19) 0.0015(19) F41 0.0560(18) 0.0317(13) 0.0575(15) -0.0107(11) -0.0262(13) -0.0051(12) F42 0.194(4) 0.0298(15) 0.0449(15) -0.0164(12) -0.0033(19) 0.0230(18) F43 0.061(2) 0.0396(16) 0.0813(19) 0.0123(13) 0.0019(16) -0.0089(14) F44 0.088(2) 0.0392(16) 0.086(2) 0.0015(14) -0.0461(18) 0.0100(15) S42 0.0327(6) 0.0216(5) 0.0400(5) -0.0109(4) -0.0100(5) -0.0011(4) S41 0.0268(6) 0.0211(5) 0.0437(6) -0.0102(4) -0.0042(4) 0.0037(4) N41 0.0271(19) 0.0205(17) 0.0390(17) -0.0077(13) -0.0043(14) 0.0017(14) N42 0.031(2) 0.0207(17) 0.0411(18) -0.0084(13) -0.0118(15) -0.0016(14) C40 0.024(2) 0.026(2) 0.0269(18) -0.0099(15) -0.0039(16) 0.0013(17) C41 0.019(2) 0.0227(19) 0.0283(18) -0.0082(15) -0.0024(15) -0.0002(16) C42 0.023(2) 0.022(2) 0.0261(18) -0.0055(14) -0.0047(15) 0.0048(16) C43 0.027(2) 0.029(2) 0.0282(19) -0.0140(15) -0.0021(16) -0.0034(17) C44 0.030(2) 0.024(2) 0.0245(18) -0.0030(15) 0.0011(16) 0.0052(17) C45 0.032(2) 0.030(2) 0.035(2) -0.0046(16) -0.0114(18) 0.0071(18) C46 0.031(2) 0.029(2) 0.035(2) -0.0088(16) -0.0114(18) -0.0010(17) C47 0.046(3) 0.027(2) 0.031(2) 0.0004(16) -0.0044(19) 0.005(2) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag F11 C13 1.344(4) . ? F12 C17 1.317(5) . ? F13 C17 1.322(5) . ? F14 C17 1.333(5) . ? S11 N11 1.637(3) . ? S11 S12 2.0952(14) . ? S12 N12 1.630(3) . ? N11 C10 1.337(5) . ? N12 C10 1.341(5) . ? C10 C11 1.476(5) . ? C11 C12 1.400(5) . ? C11 C16 1.402(5) . ? C12 C13 1.367(5) . ? C12 H12 0.9500 . ? C13 C14 1.392(5) . ? C14 C15 1.382(5) . ? C14 C17 1.492(5) . ? C15 C16 1.386(5) . ? C15 H15 0.9500 . ? C16 H16 0.9500 . ? F21 C23 1.338(4) . ? F22 C27 1.324(4) . ? F23 C27 1.329(4) . ? F24 C27 1.341(4) . ? S21 N21 1.637(3) . ? S21 S22 2.0913(14) . ? S22 N22 1.637(3) . ? N21 C20 1.335(5) . ? N22 C20 1.346(5) . ? C20 C21 1.472(5) . ? C21 C22 1.392(5) . ? C21 C26 1.393(5) . ? C22 C23 1.374(5) . ? C22 H22 0.9500 . ? C23 C24 1.393(5) . ? C24 C25 1.380(5) . ? C24 C27 1.498(5) . ? C25 C26 1.380(5) . ? C25 H25 0.9500 . ? C26 H26 0.9500 . ? F31 C33 1.349(4) . ? F32 C37 1.327(4) . ? F33 C37 1.328(5) . ? F34 C37 1.350(4) . ? S31 N31 1.634(3) . ? S31 S32 2.0888(14) . ? S32 N32 1.637(3) . ? N31 C30 1.339(5) . ? N32 C30 1.337(5) . ? C30 C31 1.476(5) . ? C31 C36 1.384(5) . ? C31 C32 1.396(5) . ? C32 C33 1.369(5) . ? C32 H32 0.9500 . ? C33 C34 1.397(5) . ? C34 C35 1.381(5) . ? C34 C37 1.497(5) . ? C35 C36 1.385(5) . ? C35 H35 0.9500 . ? C36 H36 0.9500 . ? F41 C43 1.343(4) . ? F42 C47 1.293(4) . ? F43 C47 1.314(5) . ? F44 C47 1.341(5) . ? S42 N42 1.633(3) . ? S42 S41 2.0938(14) . ? S41 N41 1.635(3) . ? N41 C40 1.336(5) . ? N42 C40 1.328(5) . ? C40 C41 1.485(5) . ? C41 C46 1.394(5) . ? C41 C42 1.396(5) . ? C42 C43 1.378(5) . ? C42 H42 0.9500 . ? C43 C44 1.390(5) . ? C44 C45 1.382(5) . ? C44 C47 1.488(5) . ? C45 C46 1.386(5) . ? C45 H45 0.9500 . ? C46 H46 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 N11 S11 S12 94.39(12) . . ? N12 S12 S11 94.78(12) . . ? C10 N11 S11 113.8(3) . . ? C10 N12 S12 113.7(3) . . ? N11 C10 N12 123.3(3) . . ? N11 C10 C11 118.8(3) . . ? N12 C10 C11 117.9(3) . . ? C12 C11 C16 119.2(3) . . ? C12 C11 C10 120.9(3) . . ? C16 C11 C10 119.9(3) . . ? C13 C12 C11 118.7(4) . . ? C13 C12 H12 120.6 . . ? C11 C12 H12 120.6 . . ? F11 C13 C12 119.1(3) . . ? F11 C13 C14 117.7(3) . . ? C12 C13 C14 123.2(3) . . ? C15 C14 C13 117.8(3) . . ? C15 C14 C17 121.5(3) . . ? C13 C14 C17 120.7(4) . . ? C14 C15 C16 120.8(4) . . ? C14 C15 H15 119.6 . . ? C16 C15 H15 119.6 . . ? C15 C16 C11 120.3(4) . . ? C15 C16 H16 119.8 . . ? C11 C16 H16 119.8 . . ? F12 C17 F13 107.3(4) . . ? F12 C17 F14 106.7(4) . . ? F13 C17 F14 105.1(3) . . ? F12 C17 C14 112.0(3) . . ? F13 C17 C14 113.0(3) . . ? F14 C17 C14 112.2(3) . . ? N21 S21 S22 94.44(12) . . ? N22 S22 S21 94.81(12) . . ? C20 N21 S21 114.2(3) . . ? C20 N22 S22 113.6(3) . . ? N21 C20 N22 122.9(3) . . ? N21 C20 C21 119.0(3) . . ? N22 C20 C21 118.0(3) . . ? C22 C21 C26 119.9(3) . . ? C22 C21 C20 119.7(3) . . ? C26 C21 C20 120.4(3) . . ? C23 C22 C21 118.7(3) . . ? C23 C22 H22 120.7 . . ? C21 C22 H22 120.7 . . ? F21 C23 C22 118.7(3) . . ? F21 C23 C24 119.1(3) . . ? C22 C23 C24 122.2(3) . . ? C25 C24 C23 118.5(3) . . ? C25 C24 C27 121.5(3) . . ? C23 C24 C27 120.1(3) . . ? C26 C25 C24 120.5(3) . . ? C26 C25 H25 119.7 . . ? C24 C25 H25 119.7 . . ? C25 C26 C21 120.3(3) . . ? C25 C26 H26 119.9 . . ? C21 C26 H26 119.9 . . ? F22 C27 F23 106.7(3) . . ? F22 C27 F24 106.8(3) . . ? F23 C27 F24 105.8(3) . . ? F22 C27 C24 112.4(3) . . ? F23 C27 C24 113.2(3) . . ? F24 C27 C24 111.7(3) . . ? N31 S31 S32 94.76(12) . . ? N32 S32 S31 94.63(12) . . ? C30 N31 S31 113.6(3) . . ? C30 N32 S32 113.6(3) . . ? N32 C30 N31 123.4(3) . . ? N32 C30 C31 117.8(3) . . ? N31 C30 C31 118.8(3) . . ? C36 C31 C32 119.3(3) . . ? C36 C31 C30 120.8(3) . . ? C32 C31 C30 119.9(3) . . ? C33 C32 C31 118.8(3) . . ? C33 C32 H32 120.6 . . ? C31 C32 H32 120.6 . . ? F31 C33 C32 119.9(3) . . ? F31 C33 C34 117.5(3) . . ? C32 C33 C34 122.6(3) . . ? C35 C34 C33 117.9(3) . . ? C35 C34 C37 122.4(3) . . ? C33 C34 C37 119.7(3) . . ? C34 C35 C36 120.3(4) . . ? C34 C35 H35 119.9 . . ? C36 C35 H35 119.9 . . ? C31 C36 C35 121.0(3) . . ? C31 C36 H36 119.5 . . ? C35 C36 H36 119.5 . . ? F32 C37 F33 106.7(3) . . ? F32 C37 F34 106.0(3) . . ? F33 C37 F34 105.7(3) . . ? F32 C37 C34 112.8(3) . . ? F33 C37 C34 113.8(3) . . ? F34 C37 C34 111.2(3) . . ? N42 S42 S41 94.48(13) . . ? N41 S41 S42 94.46(13) . . ? C40 N41 S41 113.5(3) . . ? C40 N42 S42 113.8(3) . . ? N42 C40 N41 123.7(3) . . ? N42 C40 C41 117.6(3) . . ? N41 C40 C41 118.7(3) . . ? C46 C41 C42 119.9(3) . . ? C46 C41 C40 119.7(3) . . ? C42 C41 C40 120.4(3) . . ? C43 C42 C41 118.2(3) . . ? C43 C42 H42 120.9 . . ? C41 C42 H42 120.9 . . ? F41 C43 C42 118.7(3) . . ? F41 C43 C44 118.1(3) . . ? C42 C43 C44 123.1(3) . . ? C45 C44 C43 117.6(3) . . ? C45 C44 C47 121.7(4) . . ? C43 C44 C47 120.7(4) . . ? C44 C45 C46 121.2(4) . . ? C44 C45 H45 119.4 . . ? C46 C45 H45 119.4 . . ? C45 C46 C41 120.0(4) . . ? C45 C46 H46 120.0 . . ? C41 C46 H46 120.0 . . ? F42 C47 F43 109.2(4) . . ? F42 C47 F44 105.9(4) . . ? F43 C47 F44 103.0(3) . . ? F42 C47 C44 113.5(3) . . ? F43 C47 C44 113.0(3) . . ? F44 C47 C44 111.5(3) . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag N11 S11 S12 N12 -0.89(15) . . . . ? S12 S11 N11 C10 1.8(3) . . . . ? S11 S12 N12 C10 -0.1(3) . . . . ? S11 N11 C10 N12 -2.5(5) . . . . ? S11 N11 C10 C11 176.3(2) . . . . ? S12 N12 C10 N11 1.6(5) . . . . ? S12 N12 C10 C11 -177.2(2) . . . . ? N11 C10 C11 C12 20.1(5) . . . . ? N12 C10 C11 C12 -161.1(3) . . . . ? N11 C10 C11 C16 -160.2(3) . . . . ? N12 C10 C11 C16 18.6(5) . . . . ? C16 C11 C12 C13 -0.7(5) . . . . ? C10 C11 C12 C13 179.0(3) . . . . ? C11 C12 C13 F11 -179.3(3) . . . . ? C11 C12 C13 C14 0.4(6) . . . . ? F11 C13 C14 C15 -179.4(3) . . . . ? C12 C13 C14 C15 0.9(6) . . . . ? F11 C13 C14 C17 1.6(5) . . . . ? C12 C13 C14 C17 -178.1(3) . . . . ? C13 C14 C15 C16 -1.8(5) . . . . ? C17 C14 C15 C16 177.1(3) . . . . ? C14 C15 C16 C11 1.6(6) . . . . ? C12 C11 C16 C15 -0.3(5) . . . . ? C10 C11 C16 C15 -179.9(3) . . . . ? C15 C14 C17 F12 -117.4(4) . . . . ? C13 C14 C17 F12 61.5(5) . . . . ? C15 C14 C17 F13 121.2(4) . . . . ? C13 C14 C17 F13 -59.9(5) . . . . ? C15 C14 C17 F14 2.6(5) . . . . ? C13 C14 C17 F14 -178.5(3) . . . . ? N21 S21 S22 N22 -0.68(15) . . . . ? S22 S21 N21 C20 0.1(2) . . . . ? S21 S22 N22 C20 1.2(2) . . . . ? S21 N21 C20 N22 0.8(4) . . . . ? S21 N21 C20 C21 -179.9(2) . . . . ? S22 N22 C20 N21 -1.5(4) . . . . ? S22 N22 C20 C21 179.3(2) . . . . ? N21 C20 C21 C22 22.1(5) . . . . ? N22 C20 C21 C22 -158.6(3) . . . . ? N21 C20 C21 C26 -158.1(3) . . . . ? N22 C20 C21 C26 21.2(5) . . . . ? C26 C21 C22 C23 -0.1(5) . . . . ? C20 C21 C22 C23 179.8(3) . . . . ? C21 C22 C23 F21 -178.9(3) . . . . ? C21 C22 C23 C24 0.7(5) . . . . ? F21 C23 C24 C25 179.8(3) . . . . ? C22 C23 C24 C25 0.2(5) . . . . ? F21 C23 C24 C27 0.4(5) . . . . ? C22 C23 C24 C27 -179.2(3) . . . . ? C23 C24 C25 C26 -1.8(5) . . . . ? C27 C24 C25 C26 177.6(3) . . . . ? C24 C25 C26 C21 2.4(5) . . . . ? C22 C21 C26 C25 -1.5(5) . . . . ? C20 C21 C26 C25 178.6(3) . . . . ? C25 C24 C27 F22 -118.4(4) . . . . ? C23 C24 C27 F22 61.0(5) . . . . ? C25 C24 C27 F23 120.8(4) . . . . ? C23 C24 C27 F23 -59.9(4) . . . . ? C25 C24 C27 F24 1.6(5) . . . . ? C23 C24 C27 F24 -179.1(3) . . . . ? N31 S31 S32 N32 -0.91(15) . . . . ? S32 S31 N31 C30 1.3(2) . . . . ? S31 S32 N32 C30 0.4(2) . . . . ? S32 N32 C30 N31 0.4(4) . . . . ? S32 N32 C30 C31 -178.5(2) . . . . ? S31 N31 C30 N32 -1.3(4) . . . . ? S31 N31 C30 C31 177.6(2) . . . . ? N32 C30 C31 C36 16.3(5) . . . . ? N31 C30 C31 C36 -162.7(3) . . . . ? N32 C30 C31 C32 -165.3(3) . . . . ? N31 C30 C31 C32 15.7(5) . . . . ? C36 C31 C32 C33 -0.8(5) . . . . ? C30 C31 C32 C33 -179.2(3) . . . . ? C31 C32 C33 F31 -179.0(3) . . . . ? C31 C32 C33 C34 1.0(5) . . . . ? F31 C33 C34 C35 179.7(3) . . . . ? C32 C33 C34 C35 -0.2(5) . . . . ? F31 C33 C34 C37 1.6(5) . . . . ? C32 C33 C34 C37 -178.4(3) . . . . ? C33 C34 C35 C36 -0.7(5) . . . . ? C37 C34 C35 C36 177.5(3) . . . . ? C32 C31 C36 C35 -0.1(5) . . . . ? C30 C31 C36 C35 178.4(3) . . . . ? C34 C35 C36 C31 0.8(5) . . . . ? C35 C34 C37 F32 -115.0(4) . . . . ? C33 C34 C37 F32 63.1(5) . . . . ? C35 C34 C37 F33 123.3(4) . . . . ? C33 C34 C37 F33 -58.6(4) . . . . ? C35 C34 C37 F34 4.0(5) . . . . ? C33 C34 C37 F34 -177.9(3) . . . . ? N42 S42 S41 N41 -0.99(15) . . . . ? S42 S41 N41 C40 1.9(2) . . . . ? S41 S42 N42 C40 -0.1(3) . . . . ? S42 N42 C40 N41 1.7(4) . . . . ? S42 N42 C40 C41 -175.6(2) . . . . ? S41 N41 C40 N42 -2.6(4) . . . . ? S41 N41 C40 C41 174.6(2) . . . . ? N42 C40 C41 C46 19.6(5) . . . . ? N41 C40 C41 C46 -157.7(3) . . . . ? N42 C40 C41 C42 -161.6(3) . . . . ? N41 C40 C41 C42 21.1(5) . . . . ? C46 C41 C42 C43 -1.1(5) . . . . ? C40 C41 C42 C43 -179.9(3) . . . . ? C41 C42 C43 F41 -178.8(3) . . . . ? C41 C42 C43 C44 1.1(5) . . . . ? F41 C43 C44 C45 179.8(3) . . . . ? C42 C43 C44 C45 -0.2(5) . . . . ? F41 C43 C44 C47 0.5(5) . . . . ? C42 C43 C44 C47 -179.4(3) . . . . ? C43 C44 C45 C46 -0.9(5) . . . . ? C47 C44 C45 C46 178.4(3) . . . . ? C44 C45 C46 C41 0.9(6) . . . . ? C42 C41 C46 C45 0.1(5) . . . . ? C40 C41 C46 C45 178.9(3) . . . . ? C45 C44 C47 F42 -115.7(4) . . . . ? C43 C44 C47 F42 63.5(5) . . . . ? C45 C44 C47 F43 119.3(4) . . . . ? C43 C44 C47 F43 -61.5(5) . . . . ? C45 C44 C47 F44 3.8(5) . . . . ? C43 C44 C47 F44 -177.0(3) . . . . ? #===END ######################################## ## Structure denoted 1(alpha) in text ## ######################################## data_jr0008 _database_code_CSD 214199 _chemical_name_systematic ? _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C8 H3 F4 N2 S2, 0.54 N2' ## SEE NOTE REGARDING N2 IN _exptl_special_details _chemical_formula_sum 'C8 H3 F4 N2 S2' _chemical_formula_weight 267.24 ## Including 0.54 N2, formula weight = 282.37 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' F F 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' S S 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting orthorhombic _symmetry_space_group_name_H-M Pbcn loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, -y+1/2, z+1/2' 'x+1/2, -y+1/2, -z' '-x, y, -z+1/2' '-x, -y, -z' 'x-1/2, y-1/2, -z-1/2' '-x-1/2, y-1/2, z' 'x, -y, z-1/2' _cell_length_a 17.1674(8) _cell_length_b 23.2395(11) _cell_length_c 10.6653(4) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 4255.0(3) _cell_formula_units_Z 16 _cell_measurement_temperature 180(2) _cell_measurement_reflns_used 6968 _cell_measurement_theta_min 1.00 _cell_measurement_theta_max 25.03 _exptl_crystal_description plate _exptl_crystal_colour red _exptl_crystal_size_max 0.21 _exptl_crystal_size_mid 0.16 _exptl_crystal_size_min 0.07 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.669 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 2128 _exptl_absorpt_coefficient_mu 0.528 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.888 _exptl_absorpt_correction_T_max 0.964 _exptl_absorpt_process_details 'Sortav Blessing (1995)' _exptl_special_details ; Crystals obtained by sublimation under ca. 0.33 atm. of N2. Structure contains channels containing diffuse electron density. Chemical evidence suggests that this comprises N2 molecules. The diffuse electron density could not be modelled, so was treated using the SQUEEZE procedure (van der Sluis and Spek, 1990), implemented in PLATON (Spek, 1998). The contribution of 243 electrons per unit cell was subtracted from F(obs). Before correction, R1 = 0.0929 and wR2 = 0.2886. On refinement against the corrected data, R1 = 0.0496, wR2 = 0.1449 (for the same SHELX job). This CIF contains the final structure refined against the "squeezed" data. ; _diffrn_ambient_temperature 180(2) _diffrn_radiation_wavelength 0.7107 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Nonius KappaCCD' _diffrn_measurement_method 'Thin slice \w and \f scans' _diffrn_standards_number 0 _diffrn_reflns_number 15146 _diffrn_reflns_av_R_equivalents 0.0684 _diffrn_reflns_av_sigmaI/netI 0.0667 _diffrn_reflns_limit_h_min 0 _diffrn_reflns_limit_h_max 20 _diffrn_reflns_limit_k_min -26 _diffrn_reflns_limit_k_max 27 _diffrn_reflns_limit_l_min -12 _diffrn_reflns_limit_l_max 12 _diffrn_reflns_theta_min 3.52 _diffrn_reflns_theta_max 25.01 _diffrn_measured_fraction_theta_max 0.992 _diffrn_reflns_theta_full 25.01 _diffrn_measured_fraction_theta_full 0.992 _reflns_number_total 3736 _reflns_number_gt 2292 _reflns_threshold_expression I>2\s(I) _computing_data_collection 'Collect (Nonius, 1998)' _computing_cell_refinement 'HKL Scalepack (Otwinowski & Minor, 1997)' _computing_data_reduction ; HKL Denzo and Scalepack (Otwinowski & Minor, 1997) ; _computing_structure_solution 'SIR-92 (Altomare et al., 1994)' _computing_structure_refinement 'SHELXTL v6.12 (Bruker AXS, 2001)' _computing_publication_material 'SHELXTL v6.12 (Bruker AXS, 2001)' _computing_molecular_graphics 'SHELXTL v6.12 (Bruker AXS, 2001)' _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^)+(0.0767P)^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 3736 _refine_ls_number_parameters 289 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0888 _refine_ls_R_factor_gt 0.0498 _refine_ls_wR_factor_ref 0.1360 _refine_ls_wR_factor_gt 0.1230 _refine_ls_goodness_of_fit_ref 0.945 _refine_ls_restrained_S_all 0.945 _refine_ls_shift/su_max 0.000 _refine_ls_shift/su_mean 0.000 _refine_diff_density_max 0.485 _refine_diff_density_min -0.315 _refine_diff_density_rms 0.072 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 S11 S 0.60882(6) -0.04566(4) 0.67750(8) 0.0439(3) Uani 1 1 d . . . S12 S 0.60252(6) -0.04580(4) 0.48127(8) 0.0414(3) Uani 1 1 d . . . S21 S 0.78841(6) -0.04835(4) 0.65782(9) 0.0441(3) Uani 1 1 d . . . S22 S 0.77859(6) -0.04566(4) 0.46280(8) 0.0451(3) Uani 1 1 d . . . F23 F 0.76134(13) 0.23783(9) 0.37734(19) 0.0541(6) Uani 1 1 d . . . F13 F 0.52566(13) 0.22743(9) 0.37202(18) 0.0552(6) Uani 1 1 d . . . F241 F 0.85462(14) 0.31639(9) 0.68783(19) 0.0586(6) Uani 1 1 d . . . F242 F 0.86868(14) 0.31684(9) 0.4900(2) 0.0593(6) Uani 1 1 d . . . F243 F 0.75471(14) 0.32343(10) 0.5708(2) 0.0718(8) Uani 1 1 d . . . F141 F 0.58823(14) 0.32411(9) 0.6771(2) 0.0637(7) Uani 1 1 d . . . F142 F 0.59678(14) 0.32329(9) 0.4777(2) 0.0592(7) Uani 1 1 d . . . F143 F 0.48530(13) 0.31130(10) 0.5665(2) 0.0643(7) Uani 1 1 d . . . N21 N 0.79467(18) 0.02150(13) 0.6731(2) 0.0411(8) Uani 1 1 d . . . N22 N 0.78293(18) 0.02446(13) 0.4546(2) 0.0411(8) Uani 1 1 d . . . N11 N 0.60467(18) 0.02458(12) 0.6893(3) 0.0411(8) Uani 1 1 d . . . N12 N 0.59635(17) 0.02434(12) 0.4698(3) 0.0377(7) Uani 1 1 d . . . C14 C 0.57371(19) 0.23441(14) 0.5774(3) 0.0351(8) Uani 1 1 d . . . C13 C 0.55551(19) 0.20083(16) 0.4738(3) 0.0371(9) Uani 1 1 d . . . C26 C 0.8310(2) 0.14051(15) 0.6749(3) 0.0378(9) Uani 1 1 d . . . H26 H 0.8466 0.1180 0.7449 0.045 Uiso 1 1 calc R . . C22 C 0.7768(2) 0.14639(15) 0.4678(3) 0.0355(9) Uani 1 1 d . . . H22 H 0.7560 0.1289 0.3945 0.043 Uiso 1 1 calc R . . C27 C 0.8230(2) 0.29617(16) 0.5815(3) 0.0411(9) Uani 1 1 d . . . C25 C 0.8398(2) 0.19930(14) 0.6793(3) 0.0350(9) Uani 1 1 d . . . H25 H 0.8626 0.2169 0.7509 0.042 Uiso 1 1 calc R . . C24 C 0.81539(18) 0.23325(15) 0.5785(3) 0.0309(8) Uani 1 1 d . . . C23 C 0.7851(2) 0.20472(16) 0.4753(3) 0.0374(9) Uani 1 1 d . . . C11 C 0.59094(19) 0.11501(14) 0.5797(3) 0.0321(8) Uani 1 1 d . . . C16 C 0.6099(2) 0.14746(15) 0.6842(3) 0.0381(9) Uani 1 1 d . . . H16 H 0.6293 0.1289 0.7571 0.046 Uiso 1 1 calc R . . C17 C 0.5615(2) 0.29817(17) 0.5739(3) 0.0473(10) Uani 1 1 d . . . C12 C 0.5638(2) 0.14254(15) 0.4722(3) 0.0370(9) Uani 1 1 d . . . H12 H 0.5513 0.1211 0.3991 0.044 Uiso 1 1 calc R . . C10 C 0.5985(2) 0.05176(15) 0.5795(3) 0.0346(9) Uani 1 1 d . . . C20 C 0.7920(2) 0.05034(15) 0.5652(3) 0.0357(9) Uani 1 1 d . . . C15 C 0.6011(2) 0.20645(16) 0.6837(3) 0.0415(9) Uani 1 1 d . . . H15 H 0.6139 0.2281 0.7565 0.050 Uiso 1 1 calc R . . C21 C 0.79951(19) 0.11327(15) 0.5692(3) 0.0310(8) 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 S11 0.0670(7) 0.0317(6) 0.0329(5) 0.0012(4) 0.0083(5) -0.0062(5) S12 0.0576(6) 0.0328(6) 0.0338(5) -0.0030(4) -0.0001(4) -0.0075(5) S21 0.0694(7) 0.0274(6) 0.0357(5) 0.0022(4) -0.0035(5) -0.0030(5) S22 0.0714(7) 0.0299(6) 0.0338(5) -0.0030(4) 0.0064(5) -0.0056(5) F23 0.0719(16) 0.0451(14) 0.0453(12) 0.0124(10) -0.0191(11) -0.0062(12) F13 0.0733(16) 0.0489(14) 0.0434(12) 0.0034(10) -0.0106(11) -0.0025(12) F241 0.0872(17) 0.0344(13) 0.0542(13) -0.0043(10) -0.0093(12) -0.0114(12) F242 0.0793(16) 0.0416(14) 0.0571(14) 0.0097(11) 0.0126(12) -0.0170(12) F243 0.0509(15) 0.0371(14) 0.127(2) -0.0026(13) -0.0092(14) 0.0106(12) F141 0.0885(18) 0.0399(14) 0.0626(15) -0.0136(11) -0.0047(13) -0.0008(12) F142 0.0779(17) 0.0384(14) 0.0615(14) 0.0089(11) 0.0154(12) -0.0029(12) F143 0.0534(15) 0.0512(16) 0.0883(18) -0.0035(12) 0.0025(12) 0.0131(12) N21 0.066(2) 0.0251(17) 0.0327(17) -0.0006(13) -0.0046(15) -0.0075(15) N22 0.065(2) 0.0312(18) 0.0265(16) -0.0018(13) 0.0032(14) -0.0081(16) N11 0.061(2) 0.0293(18) 0.0333(17) -0.0013(13) 0.0073(14) -0.0020(15) N12 0.0506(19) 0.0315(18) 0.0310(16) -0.0027(13) -0.0028(14) -0.0042(14) C14 0.036(2) 0.029(2) 0.040(2) -0.0052(16) 0.0081(16) -0.0032(17) C13 0.037(2) 0.045(3) 0.0299(19) 0.0093(17) -0.0045(16) -0.0011(18) C26 0.052(2) 0.034(2) 0.0274(19) 0.0025(15) -0.0011(17) -0.0009(18) C22 0.041(2) 0.036(2) 0.0295(19) 0.0002(16) -0.0003(16) -0.0073(17) C27 0.042(2) 0.034(2) 0.047(2) 0.0030(18) 0.0027(19) -0.0048(18) C25 0.046(2) 0.027(2) 0.0315(19) -0.0026(15) 0.0033(16) -0.0003(17) C24 0.0289(18) 0.029(2) 0.0345(19) -0.0026(16) 0.0076(15) -0.0017(15) C23 0.041(2) 0.038(2) 0.034(2) 0.0095(17) -0.0004(17) -0.0036(17) C11 0.0341(19) 0.032(2) 0.0304(19) 0.0017(16) 0.0060(15) -0.0033(16) C16 0.049(2) 0.038(2) 0.0271(19) 0.0015(16) 0.0006(16) -0.0009(18) C17 0.051(3) 0.048(3) 0.043(2) -0.003(2) 0.007(2) 0.007(2) C12 0.045(2) 0.033(2) 0.033(2) -0.0048(16) 0.0021(17) -0.0080(17) C10 0.041(2) 0.036(2) 0.0268(19) -0.0020(16) 0.0013(15) -0.0051(17) C20 0.046(2) 0.034(2) 0.0267(19) 0.0021(16) 0.0008(16) -0.0017(17) C15 0.049(2) 0.041(3) 0.035(2) -0.0002(18) -0.0010(17) -0.0031(18) C21 0.039(2) 0.029(2) 0.0251(18) 0.0009(15) 0.0043(15) -0.0049(16) _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 S11 N11 1.639(3) . ? S11 S12 2.0956(12) . ? S12 N12 1.638(3) . ? S21 N21 1.635(3) . ? S21 S22 2.0876(13) . ? S22 N22 1.634(3) . ? F23 C23 1.360(4) . ? F13 C13 1.350(4) . ? F241 C27 1.342(4) . ? F242 C27 1.341(4) . ? F243 C27 1.338(4) . ? F141 C17 1.336(4) . ? F142 C17 1.327(4) . ? F143 C17 1.346(4) . ? N21 C20 1.332(4) . ? N22 C20 1.334(4) . ? N11 C10 1.334(4) . ? N12 C10 1.333(4) . ? C14 C13 1.389(4) . ? C14 C15 1.389(5) . ? C14 C17 1.497(5) . ? C13 C12 1.362(5) . ? C26 C25 1.375(5) . ? C26 C21 1.402(4) . ? C26 H26 0.9500 . ? C22 C23 1.365(5) . ? C22 C21 1.384(4) . ? C22 H22 0.9500 . ? C27 C24 1.468(5) . ? C25 C24 1.398(4) . ? C25 H25 0.9500 . ? C24 C23 1.386(5) . ? C11 C16 1.384(4) . ? C11 C12 1.393(4) . ? C11 C10 1.476(5) . ? C16 C15 1.379(5) . ? C16 H16 0.9500 . ? C12 H12 0.9500 . ? C20 C21 1.469(5) . ? C15 H15 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 N11 S11 S12 94.34(11) . . ? N12 S12 S11 94.38(10) . . ? N21 S21 S22 94.30(10) . . ? N22 S22 S21 94.57(10) . . ? C20 N21 S21 114.3(2) . . ? C20 N22 S22 114.0(2) . . ? C10 N11 S11 114.1(2) . . ? C10 N12 S12 114.1(2) . . ? C13 C14 C15 117.6(3) . . ? C13 C14 C17 120.3(3) . . ? C15 C14 C17 122.1(3) . . ? F13 C13 C12 119.0(3) . . ? F13 C13 C14 117.9(3) . . ? C12 C13 C14 123.0(3) . . ? C25 C26 C21 121.2(3) . . ? C25 C26 H26 119.4 . . ? C21 C26 H26 119.4 . . ? C23 C22 C21 118.5(3) . . ? C23 C22 H22 120.8 . . ? C21 C22 H22 120.8 . . ? F243 C27 F242 106.3(3) . . ? F243 C27 F241 105.1(3) . . ? F242 C27 F241 104.7(3) . . ? F243 C27 C24 113.1(3) . . ? F242 C27 C24 113.1(3) . . ? F241 C27 C24 113.8(3) . . ? C26 C25 C24 120.1(3) . . ? C26 C25 H25 120.0 . . ? C24 C25 H25 120.0 . . ? C23 C24 C25 117.0(3) . . ? C23 C24 C27 121.8(3) . . ? C25 C24 C27 121.2(3) . . ? F23 C23 C22 119.0(3) . . ? F23 C23 C24 116.9(3) . . ? C22 C23 C24 124.1(3) . . ? C16 C11 C12 119.4(3) . . ? C16 C11 C10 121.5(3) . . ? C12 C11 C10 119.1(3) . . ? C15 C16 C11 120.9(3) . . ? C15 C16 H16 119.6 . . ? C11 C16 H16 119.6 . . ? F142 C17 F141 106.4(3) . . ? F142 C17 F143 107.4(3) . . ? F141 C17 F143 106.2(3) . . ? F142 C17 C14 113.0(3) . . ? F141 C17 C14 112.2(3) . . ? F143 C17 C14 111.2(3) . . ? C13 C12 C11 118.8(3) . . ? C13 C12 H12 120.6 . . ? C11 C12 H12 120.6 . . ? N12 C10 N11 123.1(3) . . ? N12 C10 C11 118.4(3) . . ? N11 C10 C11 118.5(3) . . ? N21 C20 N22 122.8(3) . . ? N21 C20 C21 118.2(3) . . ? N22 C20 C21 119.0(3) . . ? C16 C15 C14 120.3(3) . . ? C16 C15 H15 119.8 . . ? C14 C15 H15 119.8 . . ? C22 C21 C26 119.1(3) . . ? C22 C21 C20 120.5(3) . . ? C26 C21 C20 120.4(3) . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag N11 S11 S12 N12 -0.77(15) . . . . ? N21 S21 S22 N22 -0.43(16) . . . . ? S22 S21 N21 C20 -0.5(3) . . . . ? S21 S22 N22 C20 1.3(3) . . . . ? S12 S11 N11 C10 0.7(3) . . . . ? S11 S12 N12 C10 0.7(3) . . . . ? C15 C14 C13 F13 177.2(3) . . . . ? C17 C14 C13 F13 -1.1(5) . . . . ? C15 C14 C13 C12 -0.4(5) . . . . ? C17 C14 C13 C12 -178.6(3) . . . . ? C21 C26 C25 C24 1.7(5) . . . . ? C26 C25 C24 C23 -2.1(5) . . . . ? C26 C25 C24 C27 179.1(3) . . . . ? F243 C27 C24 C23 61.2(4) . . . . ? F242 C27 C24 C23 -59.6(4) . . . . ? F241 C27 C24 C23 -179.0(3) . . . . ? F243 C27 C24 C25 -120.0(3) . . . . ? F242 C27 C24 C25 119.1(4) . . . . ? F241 C27 C24 C25 -0.2(5) . . . . ? C21 C22 C23 F23 -178.5(3) . . . . ? C21 C22 C23 C24 0.3(5) . . . . ? C25 C24 C23 F23 180.0(3) . . . . ? C27 C24 C23 F23 -1.2(5) . . . . ? C25 C24 C23 C22 1.1(5) . . . . ? C27 C24 C23 C22 180.0(3) . . . . ? C12 C11 C16 C15 1.0(5) . . . . ? C10 C11 C16 C15 -178.8(3) . . . . ? C13 C14 C17 F142 -54.3(5) . . . . ? C15 C14 C17 F142 127.5(4) . . . . ? C13 C14 C17 F141 -174.6(3) . . . . ? C15 C14 C17 F141 7.2(5) . . . . ? C13 C14 C17 F143 66.5(4) . . . . ? C15 C14 C17 F143 -111.6(4) . . . . ? F13 C13 C12 C11 -176.8(3) . . . . ? C14 C13 C12 C11 0.7(5) . . . . ? C16 C11 C12 C13 -1.0(5) . . . . ? C10 C11 C12 C13 178.8(3) . . . . ? S12 N12 C10 N11 -0.4(4) . . . . ? S12 N12 C10 C11 -178.2(2) . . . . ? S11 N11 C10 N12 -0.4(4) . . . . ? S11 N11 C10 C11 177.4(2) . . . . ? C16 C11 C10 N12 -165.2(3) . . . . ? C12 C11 C10 N12 15.0(5) . . . . ? C16 C11 C10 N11 16.9(5) . . . . ? C12 C11 C10 N11 -162.8(3) . . . . ? S21 N21 C20 N22 1.7(5) . . . . ? S21 N21 C20 C21 -178.2(3) . . . . ? S22 N22 C20 N21 -2.1(5) . . . . ? S22 N22 C20 C21 177.8(3) . . . . ? C11 C16 C15 C14 -0.7(5) . . . . ? C13 C14 C15 C16 0.3(5) . . . . ? C17 C14 C15 C16 178.5(3) . . . . ? C23 C22 C21 C26 -0.9(5) . . . . ? C23 C22 C21 C20 -179.7(3) . . . . ? C25 C26 C21 C22 -0.1(5) . . . . ? C25 C26 C21 C20 178.8(3) . . . . ? N21 C20 C21 C22 -162.7(3) . . . . ? N22 C20 C21 C22 17.4(5) . . . . ? N21 C20 C21 C26 18.5(5) . . . . ? N22 C20 C21 C26 -161.5(3) . . . . ? #===END ####################################### ## Structure denoted 1(beta) in text ## ####################################### data_jr0123 _database_code_CSD 214200 _chemical_name_systematic ? _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C8 H3 F4 N2 S2, 0.38 CO2' ## SEE NOTE REGARDING CO2 IN _exptl_special_details _chemical_formula_sum 'C8 H3 F4 N2 S2' _chemical_formula_weight 267.24 ## Including 0.38 CO2, formula weight = 283.96 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' F F 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' S S 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting orthorhombic _symmetry_space_group_name_H-M Pbcn loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, -y+1/2, z+1/2' 'x+1/2, -y+1/2, -z' '-x, y, -z+1/2' '-x, -y, -z' 'x-1/2, y-1/2, -z-1/2' '-x-1/2, y-1/2, z' 'x, -y, z-1/2' _cell_length_a 17.1277(7) _cell_length_b 23.2356(10) _cell_length_c 10.6532(2) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 4239.7(3) _cell_formula_units_Z 16 _cell_measurement_temperature 180(2) _cell_measurement_reflns_used 13806 _cell_measurement_theta_min 1.00 _cell_measurement_theta_max 25.03 _exptl_crystal_description block _exptl_crystal_colour red _exptl_crystal_size_max 0.25 _exptl_crystal_size_mid 0.12 _exptl_crystal_size_min 0.09 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.675 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 2128 _exptl_absorpt_coefficient_mu 0.530 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.921 _exptl_absorpt_correction_T_max 0.953 _exptl_absorpt_process_details 'Sortav Blessing (1995)' _exptl_special_details ; Crystals obtained by sublimation under ca. 0.33 atm. of CO2. Structure contains channels containing diffuse electron density. Chemical evidence suggests that this comprises CO2 molecules. The diffuse electron density could not be modelled, so was treated using the SQUEEZE procedure (van der Sluis and Spek, 1990), implemented in PLATON (Spek, 1998). The contribution of 267 electrons per unit cell was subtracted from F(obs). Before correction, R1 = 0.0890 and wR2 = 0.2854. On refinement against the corrected data, R1 = 0.0519, wR2 = 0.1545 (for the same SHELX job). This CIF contains the final structure refined against the "squeezed" data. ; _diffrn_ambient_temperature 180(2) _diffrn_radiation_wavelength 0.7107 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Nonius Kappa CCD' _diffrn_measurement_method 'thin-slice \w and \f scans' _diffrn_standards_number 0 _diffrn_reflns_number 24190 _diffrn_reflns_av_R_equivalents 0.0756 _diffrn_reflns_av_sigmaI/netI 0.0546 _diffrn_reflns_limit_h_min -20 _diffrn_reflns_limit_h_max 20 _diffrn_reflns_limit_k_min -26 _diffrn_reflns_limit_k_max 27 _diffrn_reflns_limit_l_min -12 _diffrn_reflns_limit_l_max 12 _diffrn_reflns_theta_min 3.52 _diffrn_reflns_theta_max 25.03 _diffrn_measured_fraction_theta_max 0.995 _diffrn_reflns_theta_full 25.03 _diffrn_measured_fraction_theta_full 0.995 _reflns_number_total 3741 _reflns_number_gt 2512 _reflns_threshold_expression I>2\s(I) _computing_data_collection 'Collect (Nonius B.V. 1998)' _computing_cell_refinement 'HKL Scalepack (Otwinowski & Minor 1997)' _computing_data_reduction ; HKL Denzo and Scalepack (Otwinowski & Minor 1997) ; _computing_structure_solution 'SHELXS-97 (Sheldrick 1997)' _computing_structure_refinement 'SHELXL-97 (Sheldrick 1997)' _computing_publication_material 'SHELXL-97 (Sheldrick 1997)' _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^)+(0.0909P)^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 3741 _refine_ls_number_parameters 289 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0838 _refine_ls_R_factor_gt 0.0518 _refine_ls_wR_factor_ref 0.1538 _refine_ls_wR_factor_gt 0.1403 _refine_ls_goodness_of_fit_ref 1.052 _refine_ls_restrained_S_all 1.052 _refine_ls_shift/su_max 0.000 _refine_ls_shift/su_mean 0.000 _refine_diff_density_max 0.566 _refine_diff_density_min -0.363 _refine_diff_density_rms 0.078 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 S11 S 0.60897(6) -0.04572(4) 0.67844(8) 0.0412(3) Uani 1 1 d . . . S12 S 0.60252(6) -0.04585(4) 0.48180(8) 0.0384(3) Uani 1 1 d . . . S21 S 0.78876(6) -0.04838(4) 0.65870(9) 0.0411(3) Uani 1 1 d . . . S22 S 0.77902(7) -0.04575(4) 0.46323(8) 0.0414(3) Uani 1 1 d . . . F23 F 0.76089(13) 0.23781(8) 0.37777(18) 0.0489(6) Uani 1 1 d . . . F13 F 0.52515(13) 0.22780(9) 0.37231(17) 0.0493(6) Uani 1 1 d . . . F241 F 0.85491(14) 0.31661(9) 0.68878(19) 0.0534(6) Uani 1 1 d . . . F242 F 0.86852(15) 0.31721(9) 0.49052(19) 0.0538(6) Uani 1 1 d . . . F243 F 0.75438(15) 0.32365(10) 0.5719(2) 0.0652(7) Uani 1 1 d . . . F141 F 0.58785(15) 0.32441(9) 0.6780(2) 0.0567(7) Uani 1 1 d . . . F142 F 0.59655(15) 0.32351(9) 0.4780(2) 0.0542(7) Uani 1 1 d . . . F143 F 0.48500(14) 0.31155(10) 0.5668(2) 0.0597(7) Uani 1 1 d . . . N21 N 0.79495(19) 0.02160(13) 0.6744(2) 0.0372(8) Uani 1 1 d . . . N22 N 0.7833(2) 0.02460(13) 0.4546(2) 0.0389(8) Uani 1 1 d . . . N11 N 0.60475(18) 0.02443(12) 0.6909(2) 0.0376(8) Uani 1 1 d . . . N12 N 0.59658(18) 0.02410(13) 0.4700(3) 0.0366(7) Uani 1 1 d . . . C14 C 0.5735(2) 0.23472(15) 0.5782(3) 0.0345(8) Uani 1 1 d . . . C13 C 0.5549(2) 0.20104(15) 0.4741(3) 0.0331(8) Uani 1 1 d . . . C26 C 0.8312(2) 0.14028(15) 0.6762(3) 0.0353(9) Uani 1 1 d . . . H26 H 0.8461 0.1177 0.7466 0.042 Uiso 1 1 calc R . . C22 C 0.7769(2) 0.14642(15) 0.4683(3) 0.0319(8) Uani 1 1 d . . . H22 H 0.7561 0.1288 0.3951 0.038 Uiso 1 1 calc R . . C27 C 0.8231(2) 0.29625(16) 0.5821(3) 0.0372(9) Uani 1 1 d . . . C25 C 0.8405(2) 0.19895(15) 0.6800(3) 0.0339(9) Uani 1 1 d . . . H25 H 0.8638 0.2164 0.7513 0.041 Uiso 1 1 calc R . . C24 C 0.8156(2) 0.23331(15) 0.5789(3) 0.0296(8) Uani 1 1 d . . . C23 C 0.7847(2) 0.20489(15) 0.4753(3) 0.0331(8) Uani 1 1 d . . . C11 C 0.5908(2) 0.11501(15) 0.5798(3) 0.0315(8) Uani 1 1 d . . . C16 C 0.6100(2) 0.14747(15) 0.6850(3) 0.0349(9) Uani 1 1 d . . . H16 H 0.6295 0.1289 0.7581 0.042 Uiso 1 1 calc R . . C17 C 0.5610(2) 0.29864(17) 0.5739(3) 0.0420(10) Uani 1 1 d . . . C12 C 0.5632(2) 0.14290(15) 0.4719(3) 0.0351(9) Uani 1 1 d . . . H12 H 0.5506 0.1215 0.3986 0.042 Uiso 1 1 calc R . . C10 C 0.5985(2) 0.05179(15) 0.5810(3) 0.0330(9) Uani 1 1 d . . . C20 C 0.7923(2) 0.05040(15) 0.5659(3) 0.0347(9) Uani 1 1 d . . . C15 C 0.6010(2) 0.20664(16) 0.6839(3) 0.0391(9) Uani 1 1 d . . . H15 H 0.6139 0.2283 0.7566 0.047 Uiso 1 1 calc R . . C21 C 0.8001(2) 0.11330(15) 0.5702(3) 0.0295(8) 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 S11 0.0661(8) 0.0272(6) 0.0303(5) 0.0015(4) 0.0083(4) -0.0037(5) S12 0.0560(7) 0.0279(6) 0.0311(5) -0.0026(4) -0.0007(4) -0.0041(4) S21 0.0671(7) 0.0230(5) 0.0332(5) 0.0026(4) -0.0041(4) -0.0015(5) S22 0.0693(8) 0.0243(6) 0.0306(5) -0.0026(4) 0.0058(4) -0.0022(5) F23 0.0711(17) 0.0351(13) 0.0406(11) 0.0131(9) -0.0174(10) -0.0052(11) F13 0.0680(16) 0.0422(14) 0.0379(12) 0.0028(9) -0.0101(10) -0.0004(11) F241 0.0827(18) 0.0298(13) 0.0477(13) -0.0050(9) -0.0085(11) -0.0118(12) F242 0.0729(17) 0.0387(14) 0.0498(13) 0.0083(10) 0.0118(11) -0.0177(12) F243 0.0502(16) 0.0328(14) 0.112(2) -0.0035(12) -0.0088(14) 0.0087(12) F141 0.0831(18) 0.0333(14) 0.0538(13) -0.0123(10) -0.0039(12) -0.0031(12) F142 0.0735(18) 0.0343(14) 0.0547(13) 0.0076(10) 0.0142(12) -0.0030(11) F143 0.0509(17) 0.0463(16) 0.0819(17) -0.0034(12) 0.0015(12) 0.0129(12) N21 0.063(2) 0.0200(17) 0.0286(16) 0.0024(12) -0.0053(13) -0.0069(14) N22 0.066(2) 0.0255(18) 0.0249(15) -0.0024(12) 0.0045(13) -0.0009(16) N11 0.061(2) 0.0233(17) 0.0284(16) -0.0017(12) 0.0057(13) -0.0028(15) N12 0.051(2) 0.0308(18) 0.0276(15) -0.0025(13) -0.0008(13) -0.0023(15) C14 0.040(2) 0.027(2) 0.0364(19) -0.0026(15) 0.0068(15) -0.0013(17) C13 0.036(2) 0.032(2) 0.0305(18) 0.0053(15) -0.0044(15) -0.0007(17) C26 0.050(3) 0.032(2) 0.0244(17) 0.0022(14) -0.0010(15) 0.0025(17) C22 0.043(2) 0.028(2) 0.0245(17) -0.0025(14) 0.0021(14) -0.0036(17) C27 0.043(2) 0.027(2) 0.042(2) 0.0022(15) -0.0026(17) -0.0034(18) C25 0.044(2) 0.026(2) 0.0314(18) -0.0045(14) 0.0044(15) -0.0012(17) C24 0.032(2) 0.026(2) 0.0315(19) 0.0000(14) 0.0068(14) -0.0010(16) C23 0.040(2) 0.031(2) 0.0285(18) 0.0068(15) 0.0009(15) -0.0016(17) C11 0.038(2) 0.027(2) 0.0298(18) -0.0015(14) 0.0039(14) 0.0009(16) C16 0.049(2) 0.031(2) 0.0249(18) -0.0012(14) -0.0006(15) 0.0008(17) C17 0.045(3) 0.042(2) 0.040(2) -0.0048(17) 0.0034(17) 0.006(2) C12 0.042(2) 0.035(2) 0.0278(18) -0.0042(15) 0.0004(15) -0.0084(18) C10 0.045(2) 0.029(2) 0.0252(19) -0.0015(14) 0.0021(14) -0.0048(17) C20 0.047(2) 0.029(2) 0.028(2) -0.0007(14) 0.0018(15) -0.0014(17) C15 0.047(3) 0.036(2) 0.034(2) -0.0058(16) 0.0005(16) -0.0027(18) C21 0.040(2) 0.021(2) 0.0271(18) 0.0018(14) 0.0068(14) -0.0019(16) _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 S11 N11 1.637(3) . ? S11 S12 2.0978(12) . ? S12 N12 1.633(3) . ? S21 N21 1.638(3) . ? S21 S22 2.0900(12) . ? S22 N22 1.639(3) . ? F23 C23 1.353(4) . ? F13 C13 1.349(4) . ? F241 C27 1.347(4) . ? F242 C27 1.340(4) . ? F243 C27 1.342(4) . ? F141 C17 1.342(4) . ? F142 C17 1.322(4) . ? F143 C17 1.337(4) . ? N21 C20 1.336(4) . ? N22 C20 1.337(4) . ? N11 C10 1.336(4) . ? N12 C10 1.346(4) . ? C14 C15 1.384(5) . ? C14 C13 1.394(5) . ? C14 C17 1.501(5) . ? C13 C12 1.359(5) . ? C26 C25 1.373(5) . ? C26 C21 1.397(4) . ? C26 H26 0.9500 . ? C22 C23 1.367(5) . ? C22 C21 1.388(4) . ? C22 H22 0.9500 . ? C27 C24 1.468(5) . ? C25 C24 1.407(5) . ? C25 H25 0.9500 . ? C24 C23 1.390(5) . ? C11 C16 1.390(4) . ? C11 C12 1.402(5) . ? C11 C10 1.475(5) . ? C16 C15 1.384(5) . ? C16 H16 0.9500 . ? C12 H12 0.9500 . ? C20 C21 1.468(5) . ? C15 H15 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 N11 S11 S12 94.58(10) . . ? N12 S12 S11 94.50(10) . . ? N21 S21 S22 94.46(10) . . ? N22 S22 S21 94.66(10) . . ? C20 N21 S21 114.0(2) . . ? C20 N22 S22 113.7(2) . . ? C10 N11 S11 114.0(2) . . ? C10 N12 S12 114.0(2) . . ? C15 C14 C13 117.4(3) . . ? C15 C14 C17 122.7(3) . . ? C13 C14 C17 119.9(3) . . ? F13 C13 C12 119.0(3) . . ? F13 C13 C14 117.8(3) . . ? C12 C13 C14 123.2(3) . . ? C25 C26 C21 120.9(3) . . ? C25 C26 H26 119.5 . . ? C21 C26 H26 119.5 . . ? C23 C22 C21 118.7(3) . . ? C23 C22 H22 120.6 . . ? C21 C22 H22 120.6 . . ? F242 C27 F243 106.1(3) . . ? F242 C27 F241 104.6(3) . . ? F243 C27 F241 104.9(3) . . ? F242 C27 C24 113.3(3) . . ? F243 C27 C24 113.2(3) . . ? F241 C27 C24 113.9(3) . . ? C26 C25 C24 120.4(3) . . ? C26 C25 H25 119.8 . . ? C24 C25 H25 119.8 . . ? C23 C24 C25 117.0(3) . . ? C23 C24 C27 121.7(3) . . ? C25 C24 C27 121.4(3) . . ? F23 C23 C22 119.4(3) . . ? F23 C23 C24 117.1(3) . . ? C22 C23 C24 123.5(3) . . ? C16 C11 C12 119.4(3) . . ? C16 C11 C10 120.8(3) . . ? C12 C11 C10 119.8(3) . . ? C15 C16 C11 120.4(3) . . ? C15 C16 H16 119.8 . . ? C11 C16 H16 119.8 . . ? F142 C17 F143 107.9(3) . . ? F142 C17 F141 106.6(3) . . ? F143 C17 F141 106.3(3) . . ? F142 C17 C14 113.0(3) . . ? F143 C17 C14 111.3(3) . . ? F141 C17 C14 111.5(3) . . ? C13 C12 C11 118.7(3) . . ? C13 C12 H12 120.6 . . ? C11 C12 H12 120.6 . . ? N11 C10 N12 122.9(3) . . ? N11 C10 C11 119.2(3) . . ? N12 C10 C11 117.8(3) . . ? N21 C20 N22 123.1(3) . . ? N21 C20 C21 117.9(3) . . ? N22 C20 C21 119.0(3) . . ? C16 C15 C14 120.9(3) . . ? C16 C15 H15 119.5 . . ? C14 C15 H15 119.5 . . ? C22 C21 C26 119.5(3) . . ? C22 C21 C20 120.1(3) . . ? C26 C21 C20 120.4(3) . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag N11 S11 S12 N12 -0.56(16) . . . . ? N21 S21 S22 N22 -0.41(16) . . . . ? S22 S21 N21 C20 -0.5(3) . . . . ? S21 S22 N22 C20 1.3(3) . . . . ? S12 S11 N11 C10 0.6(3) . . . . ? S11 S12 N12 C10 0.4(3) . . . . ? C15 C14 C13 F13 177.5(3) . . . . ? C17 C14 C13 F13 -0.6(5) . . . . ? C15 C14 C13 C12 -0.6(5) . . . . ? C17 C14 C13 C12 -178.7(3) . . . . ? C21 C26 C25 C24 2.8(5) . . . . ? C26 C25 C24 C23 -2.4(5) . . . . ? C26 C25 C24 C27 178.4(3) . . . . ? F242 C27 C24 C23 -60.0(5) . . . . ? F243 C27 C24 C23 61.0(4) . . . . ? F241 C27 C24 C23 -179.3(3) . . . . ? F242 C27 C24 C25 119.1(4) . . . . ? F243 C27 C24 C25 -120.0(3) . . . . ? F241 C27 C24 C25 -0.2(5) . . . . ? C21 C22 C23 F23 -178.7(3) . . . . ? C21 C22 C23 C24 0.8(5) . . . . ? C25 C24 C23 F23 -179.8(3) . . . . ? C27 C24 C23 F23 -0.7(5) . . . . ? C25 C24 C23 C22 0.6(5) . . . . ? C27 C24 C23 C22 179.8(3) . . . . ? C12 C11 C16 C15 0.9(5) . . . . ? C10 C11 C16 C15 -178.6(3) . . . . ? C15 C14 C17 F142 127.0(4) . . . . ? C13 C14 C17 F142 -55.0(5) . . . . ? C15 C14 C17 F143 -111.5(4) . . . . ? C13 C14 C17 F143 66.5(4) . . . . ? C15 C14 C17 F141 7.0(5) . . . . ? C13 C14 C17 F141 -175.0(3) . . . . ? F13 C13 C12 C11 -177.2(3) . . . . ? C14 C13 C12 C11 0.9(5) . . . . ? C16 C11 C12 C13 -1.0(5) . . . . ? C10 C11 C12 C13 178.5(3) . . . . ? S11 N11 C10 N12 -0.5(5) . . . . ? S11 N11 C10 C11 177.4(3) . . . . ? S12 N12 C10 N11 0.0(5) . . . . ? S12 N12 C10 C11 -178.0(3) . . . . ? C16 C11 C10 N11 17.0(5) . . . . ? C12 C11 C10 N11 -162.6(3) . . . . ? C16 C11 C10 N12 -165.0(3) . . . . ? C12 C11 C10 N12 15.4(5) . . . . ? S21 N21 C20 N22 1.6(5) . . . . ? S21 N21 C20 C21 -178.0(3) . . . . ? S22 N22 C20 N21 -2.0(5) . . . . ? S22 N22 C20 C21 177.6(3) . . . . ? C11 C16 C15 C14 -0.6(5) . . . . ? C13 C14 C15 C16 0.4(5) . . . . ? C17 C14 C15 C16 178.5(3) . . . . ? C23 C22 C21 C26 -0.6(5) . . . . ? C23 C22 C21 C20 179.7(3) . . . . ? C25 C26 C21 C22 -1.2(5) . . . . ? C25 C26 C21 C20 178.4(3) . . . . ? N21 C20 C21 C22 -162.4(3) . . . . ? N22 C20 C21 C22 18.0(5) . . . . ? N21 C20 C21 C26 17.9(5) . . . . ? N22 C20 C21 C26 -161.7(3) . . . . ? #===END ######################################## ## Structure denoted 1(gamma) in text ## ######################################## data_jr0116 _database_code_CSD 214201 _chemical_name_systematic ? _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C8 H3 F4 N2 S2, 0.94Ar' ## SEE NOTE REGARDING Ar IN _exptl_special_details _chemical_formula_sum 'C8 H3 F4 N2 S2' _chemical_formula_weight 267.24 ## Including 0.94 N2, formula weight = 304.79 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' F F 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' S S 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting orthorhombic _symmetry_space_group_name_H-M Pbcn loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, -y+1/2, z+1/2' 'x+1/2, -y+1/2, -z' '-x, y, -z+1/2' '-x, -y, -z' 'x-1/2, y-1/2, -z-1/2' '-x-1/2, y-1/2, z' 'x, -y, z-1/2' _cell_length_a 17.1483(6) _cell_length_b 23.2411(8) _cell_length_c 10.6610(2) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 4248.9(2) _cell_formula_units_Z 16 _cell_measurement_temperature 180(2) _cell_measurement_reflns_used 15588 _cell_measurement_theta_min 1.00 _cell_measurement_theta_max 25.03 _exptl_crystal_description block _exptl_crystal_colour red _exptl_crystal_size_max 0.21 _exptl_crystal_size_mid 0.16 _exptl_crystal_size_min 0.07 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.671 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 2128 _exptl_absorpt_coefficient_mu 0.528 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.854 _exptl_absorpt_correction_T_max 0.964 _exptl_absorpt_process_details 'Sortav Blessing (1995)' _exptl_special_details ; Crystals obtained by sublimation under ca. 0.33 atm. of Ar. Structure contains channels containing diffuse electron density. Chemical evidence suggests that this comprises Ar molecules. The diffuse electron density could not be modelled, so was treated using the SQUEEZE procedure (van der Sluis and Spek, 1990), implemented in PLATON (Spek, 1998). The contribution of 270 electrons per unit cell was subtracted from F(obs). Before correction, R1 = 0.0897 and wR2 = 0.2913. On refinement against the corrected data, R1 = 0.0479, wR2 = 0.1512 (for the same SHELX job). This CIF contains the final structure refined against the "squeezed" data. ; _diffrn_ambient_temperature 180(2) _diffrn_radiation_wavelength 0.7107 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Nonius KappaCCD' _diffrn_measurement_method 'Thin slice \w and \f scans' _diffrn_standards_number 0 _diffrn_reflns_number 23982 _diffrn_reflns_av_R_equivalents 0.0636 _diffrn_reflns_av_sigmaI/netI 0.0437 _diffrn_reflns_limit_h_min -20 _diffrn_reflns_limit_h_max 20 _diffrn_reflns_limit_k_min -27 _diffrn_reflns_limit_k_max 26 _diffrn_reflns_limit_l_min -12 _diffrn_reflns_limit_l_max 12 _diffrn_reflns_theta_min 3.52 _diffrn_reflns_theta_max 25.02 _diffrn_measured_fraction_theta_max 0.996 _diffrn_reflns_theta_full 25.02 _diffrn_measured_fraction_theta_full 0.996 _reflns_number_total 3753 _reflns_number_gt 2801 _reflns_threshold_expression I>2\s(I) _computing_data_collection 'Collect (Nonius, 1998)' _computing_cell_refinement 'HKL Scalepack (Otwinowski & Minor, 1997)' _computing_data_reduction ; HKL Denzo and Scalepack (Otwinowski & Minor, 1997) ; _computing_structure_solution 'SIR-92 (Altomare et al., 1994)' _computing_structure_refinement 'SHELXTL v6.12 (Bruker AXS, 2001)' _computing_publication_material 'SHELXTL v6.12 (Bruker AXS, 2001)' _computing_molecular_graphics 'SHELXTL v6.12 (Bruker AXS, 2001)' _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^)+(0.1015P)^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 3753 _refine_ls_number_parameters 289 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0666 _refine_ls_R_factor_gt 0.0483 _refine_ls_wR_factor_ref 0.1504 _refine_ls_wR_factor_gt 0.1411 _refine_ls_goodness_of_fit_ref 1.035 _refine_ls_restrained_S_all 1.035 _refine_ls_shift/su_max 0.000 _refine_ls_shift/su_mean 0.000 _refine_diff_density_max 0.698 _refine_diff_density_min -0.347 _refine_diff_density_rms 0.105 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 S11 S 0.60886(5) -0.04566(3) 0.67774(7) 0.0415(3) Uani 1 1 d . . . S12 S 0.60245(5) -0.04586(3) 0.48132(7) 0.0387(3) Uani 1 1 d . . . S21 S 0.78858(5) -0.04841(3) 0.65819(8) 0.0410(3) Uani 1 1 d . . . S22 S 0.77873(6) -0.04569(3) 0.46285(7) 0.0418(3) Uani 1 1 d . . . F23 F 0.76110(12) 0.23775(7) 0.37719(16) 0.0504(5) Uani 1 1 d . . . F13 F 0.52537(11) 0.22774(8) 0.37197(15) 0.0497(5) Uani 1 1 d . . . F241 F 0.85457(13) 0.31656(8) 0.68843(16) 0.0541(5) Uani 1 1 d . . . F242 F 0.86869(13) 0.31725(8) 0.48998(17) 0.0560(5) Uani 1 1 d . . . F243 F 0.75473(13) 0.32348(9) 0.5710(2) 0.0678(7) Uani 1 1 d . . . F141 F 0.58803(13) 0.32413(8) 0.67753(18) 0.0593(6) Uani 1 1 d . . . F142 F 0.59670(13) 0.32346(8) 0.47774(18) 0.0565(6) Uani 1 1 d . . . F143 F 0.48494(12) 0.31125(9) 0.56668(19) 0.0607(6) Uani 1 1 d . . . N21 N 0.79513(16) 0.02169(11) 0.6734(2) 0.0380(6) Uani 1 1 d . . . N22 N 0.78322(16) 0.02453(12) 0.4545(2) 0.0385(6) Uani 1 1 d . . . N11 N 0.60476(15) 0.02453(11) 0.6897(2) 0.0379(6) Uani 1 1 d . . . N12 N 0.59664(15) 0.02431(11) 0.4701(2) 0.0365(6) Uani 1 1 d . . . C14 C 0.57341(17) 0.23439(13) 0.5770(2) 0.0343(7) Uani 1 1 d . . . C13 C 0.55487(17) 0.20104(13) 0.4736(3) 0.0354(7) Uani 1 1 d . . . C26 C 0.83118(18) 0.14026(12) 0.6760(2) 0.0353(7) Uani 1 1 d . . . H26 H 0.8465 0.1177 0.7460 0.042 Uiso 1 1 calc R . . C22 C 0.77692(17) 0.14656(13) 0.4677(3) 0.0332(7) Uani 1 1 d . . . H22 H 0.7560 0.1291 0.3945 0.040 Uiso 1 1 calc R . . C27 C 0.82260(18) 0.29631(14) 0.5822(3) 0.0376(7) Uani 1 1 d . . . C25 C 0.83976(17) 0.19891(13) 0.6800(3) 0.0349(7) Uani 1 1 d . . . H25 H 0.8624 0.2164 0.7518 0.042 Uiso 1 1 calc R . . C24 C 0.81550(16) 0.23332(13) 0.5792(2) 0.0292(7) Uani 1 1 d . . . C23 C 0.78487(17) 0.20496(13) 0.4752(3) 0.0338(7) Uani 1 1 d . . . C11 C 0.59072(17) 0.11502(13) 0.5790(2) 0.0320(7) Uani 1 1 d . . . C16 C 0.60987(18) 0.14744(13) 0.6847(2) 0.0366(7) Uani 1 1 d . . . H16 H 0.6287 0.1288 0.7579 0.044 Uiso 1 1 calc R . . C17 C 0.5612(2) 0.29804(15) 0.5744(3) 0.0443(8) Uani 1 1 d . . . C12 C 0.56334(17) 0.14260(13) 0.4719(3) 0.0343(7) Uani 1 1 d . . . H12 H 0.5507 0.1211 0.3989 0.041 Uiso 1 1 calc R . . C10 C 0.59852(18) 0.05145(13) 0.5797(2) 0.0338(7) Uani 1 1 d . . . C20 C 0.79211(18) 0.05009(12) 0.5654(2) 0.0338(8) Uani 1 1 d . . . C15 C 0.60160(18) 0.20635(13) 0.6835(3) 0.0394(8) Uani 1 1 d . . . H15 H 0.6152 0.2281 0.7557 0.047 Uiso 1 1 calc R . . C21 C 0.80002(16) 0.11331(13) 0.5694(2) 0.0303(7) 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 S11 0.0659(6) 0.0281(5) 0.0307(4) 0.0021(3) 0.0080(4) -0.0048(4) S12 0.0560(6) 0.0279(5) 0.0321(4) -0.0035(3) -0.0006(3) -0.0056(3) S21 0.0660(6) 0.0240(5) 0.0330(4) 0.0021(3) -0.0035(3) -0.0024(4) S22 0.0686(6) 0.0258(5) 0.0310(4) -0.0030(3) 0.0067(4) -0.0041(4) F23 0.0704(14) 0.0386(11) 0.0421(10) 0.0127(8) -0.0180(9) -0.0059(9) F13 0.0672(13) 0.0442(11) 0.0379(10) 0.0046(8) -0.0124(8) -0.0019(9) F241 0.0821(15) 0.0322(11) 0.0479(11) -0.0057(8) -0.0084(9) -0.0111(10) F242 0.0767(14) 0.0382(11) 0.0531(11) 0.0085(8) 0.0117(10) -0.0167(10) F243 0.0518(14) 0.0338(12) 0.118(2) -0.0040(10) -0.0076(11) 0.0084(10) F141 0.0854(15) 0.0369(11) 0.0557(12) -0.0128(9) -0.0037(10) -0.0023(10) F142 0.0766(15) 0.0365(12) 0.0563(12) 0.0084(9) 0.0138(10) -0.0018(10) F143 0.0497(13) 0.0461(13) 0.0862(15) -0.0035(10) 0.0043(10) 0.0115(10) N21 0.0604(18) 0.0247(14) 0.0288(13) 0.0009(10) -0.0021(11) -0.0048(12) N22 0.0618(18) 0.0278(15) 0.0258(13) -0.0011(10) 0.0050(11) -0.0035(13) N11 0.0598(18) 0.0250(14) 0.0290(13) -0.0001(10) 0.0058(11) -0.0035(12) N12 0.0498(16) 0.0316(14) 0.0283(13) -0.0027(11) -0.0003(10) -0.0028(12) C14 0.0359(17) 0.0280(16) 0.0391(17) -0.0006(12) 0.0088(12) -0.0040(13) C13 0.0341(16) 0.0403(19) 0.0316(15) 0.0091(13) -0.0025(12) -0.0017(14) C26 0.051(2) 0.0267(17) 0.0276(15) 0.0012(11) 0.0001(13) -0.0016(14) C22 0.0436(18) 0.0312(17) 0.0247(14) -0.0004(12) 0.0000(12) -0.0039(14) C27 0.0380(18) 0.0311(18) 0.0436(18) 0.0018(13) 0.0011(13) -0.0032(14) C25 0.0441(19) 0.0294(17) 0.0311(15) -0.0032(12) 0.0024(12) -0.0038(14) C24 0.0285(16) 0.0259(16) 0.0333(16) 0.0001(11) 0.0075(11) -0.0016(12) C23 0.0371(17) 0.0326(18) 0.0318(15) 0.0069(13) 0.0004(12) -0.0030(13) C11 0.0373(16) 0.0302(17) 0.0285(15) -0.0008(11) 0.0061(11) -0.0035(13) C16 0.052(2) 0.0329(18) 0.0251(15) -0.0004(12) -0.0014(13) 0.0014(14) C17 0.051(2) 0.043(2) 0.0397(18) -0.0032(14) 0.0070(14) 0.0055(16) C12 0.0396(18) 0.0355(18) 0.0278(14) -0.0040(12) -0.0004(12) -0.0056(14) C10 0.0403(18) 0.0356(19) 0.0254(16) -0.0014(12) 0.0011(12) -0.0039(13) C20 0.0451(19) 0.0292(19) 0.0270(17) -0.0014(12) 0.0009(12) -0.0035(13) C15 0.051(2) 0.0320(18) 0.0348(16) -0.0057(13) -0.0001(13) -0.0013(15) C21 0.0372(17) 0.0268(17) 0.0271(15) 0.0022(11) 0.0058(11) -0.0034(13) _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 S11 N11 1.638(3) . ? S11 S12 2.0969(10) . ? S12 N12 1.638(3) . ? S21 N21 1.641(3) . ? S21 S22 2.0903(11) . ? S22 N22 1.636(3) . ? F23 C23 1.356(3) . ? F13 C13 1.347(3) . ? F241 C27 1.343(3) . ? F242 C27 1.352(3) . ? F243 C27 1.329(4) . ? F141 C17 1.337(4) . ? F142 C17 1.335(4) . ? F143 C17 1.345(4) . ? N21 C20 1.328(4) . ? N22 C20 1.332(4) . ? N11 C10 1.334(4) . ? N12 C10 1.328(4) . ? C14 C13 1.385(4) . ? C14 C15 1.395(4) . ? C14 C17 1.494(4) . ? C13 C12 1.366(4) . ? C26 C25 1.372(4) . ? C26 C21 1.403(4) . ? C26 H26 0.9500 . ? C22 C23 1.367(4) . ? C22 C21 1.389(4) . ? C22 H22 0.9500 . ? C27 C24 1.469(4) . ? C25 C24 1.402(4) . ? C25 H25 0.9500 . ? C24 C23 1.393(4) . ? C11 C12 1.391(4) . ? C11 C16 1.394(4) . ? C11 C10 1.483(4) . ? C16 C15 1.376(4) . ? C16 H16 0.9500 . ? C12 H12 0.9500 . ? C20 C21 1.476(4) . ? C15 H15 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 N11 S11 S12 94.47(9) . . ? N12 S12 S11 94.23(9) . . ? N21 S21 S22 94.26(9) . . ? N22 S22 S21 94.62(9) . . ? C20 N21 S21 113.9(2) . . ? C20 N22 S22 113.7(2) . . ? C10 N11 S11 113.7(2) . . ? C10 N12 S12 114.0(2) . . ? C13 C14 C15 117.8(3) . . ? C13 C14 C17 120.5(3) . . ? C15 C14 C17 121.7(3) . . ? F13 C13 C12 119.2(2) . . ? F13 C13 C14 118.0(3) . . ? C12 C13 C14 122.8(3) . . ? C25 C26 C21 120.6(3) . . ? C25 C26 H26 119.7 . . ? C21 C26 H26 119.7 . . ? C23 C22 C21 118.6(3) . . ? C23 C22 H22 120.7 . . ? C21 C22 H22 120.7 . . ? F243 C27 F241 105.4(2) . . ? F243 C27 F242 106.0(2) . . ? F241 C27 F242 104.4(2) . . ? F243 C27 C24 113.5(3) . . ? F241 C27 C24 113.6(2) . . ? F242 C27 C24 113.0(2) . . ? C26 C25 C24 120.7(3) . . ? C26 C25 H25 119.6 . . ? C24 C25 H25 119.6 . . ? C23 C24 C25 116.9(3) . . ? C23 C24 C27 121.3(2) . . ? C25 C24 C27 121.8(3) . . ? F23 C23 C22 118.9(3) . . ? F23 C23 C24 117.5(3) . . ? C22 C23 C24 123.7(3) . . ? C12 C11 C16 119.6(3) . . ? C12 C11 C10 119.6(2) . . ? C16 C11 C10 120.9(2) . . ? C15 C16 C11 120.4(3) . . ? C15 C16 H16 119.8 . . ? C11 C16 H16 119.8 . . ? F142 C17 F141 106.1(3) . . ? F142 C17 F143 107.2(3) . . ? F141 C17 F143 106.4(2) . . ? F142 C17 C14 112.8(2) . . ? F141 C17 C14 112.7(3) . . ? F143 C17 C14 111.3(3) . . ? C13 C12 C11 118.9(3) . . ? C13 C12 H12 120.5 . . ? C11 C12 H12 120.5 . . ? N12 C10 N11 123.6(3) . . ? N12 C10 C11 117.8(2) . . ? N11 C10 C11 118.6(2) . . ? N21 C20 N22 123.5(3) . . ? N21 C20 C21 117.8(2) . . ? N22 C20 C21 118.7(2) . . ? C16 C15 C14 120.5(3) . . ? C16 C15 H15 119.7 . . ? C14 C15 H15 119.7 . . ? C22 C21 C26 119.5(3) . . ? C22 C21 C20 120.4(2) . . ? C26 C21 C20 120.1(2) . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag N11 S11 S12 N12 -0.57(13) . . . . ? N21 S21 S22 N22 -0.51(14) . . . . ? S22 S21 N21 C20 -0.2(2) . . . . ? S21 S22 N22 C20 1.1(2) . . . . ? S12 S11 N11 C10 0.7(2) . . . . ? S11 S12 N12 C10 0.3(2) . . . . ? C15 C14 C13 F13 178.0(3) . . . . ? C17 C14 C13 F13 -0.3(4) . . . . ? C15 C14 C13 C12 -0.3(4) . . . . ? C17 C14 C13 C12 -178.5(3) . . . . ? C21 C26 C25 C24 1.9(4) . . . . ? C26 C25 C24 C23 -1.8(4) . . . . ? C26 C25 C24 C27 178.8(3) . . . . ? F243 C27 C24 C23 60.6(4) . . . . ? F241 C27 C24 C23 -178.9(3) . . . . ? F242 C27 C24 C23 -60.1(4) . . . . ? F243 C27 C24 C25 -119.9(3) . . . . ? F241 C27 C24 C25 0.5(4) . . . . ? F242 C27 C24 C25 119.3(3) . . . . ? C21 C22 C23 F23 -178.8(3) . . . . ? C21 C22 C23 C24 0.5(4) . . . . ? C25 C24 C23 F23 179.9(3) . . . . ? C27 C24 C23 F23 -0.6(4) . . . . ? C25 C24 C23 C22 0.6(4) . . . . ? C27 C24 C23 C22 -179.9(3) . . . . ? C12 C11 C16 C15 0.2(4) . . . . ? C10 C11 C16 C15 -179.3(3) . . . . ? C13 C14 C17 F142 -54.7(4) . . . . ? C15 C14 C17 F142 127.1(3) . . . . ? C13 C14 C17 F141 -174.8(3) . . . . ? C15 C14 C17 F141 7.0(4) . . . . ? C13 C14 C17 F143 65.8(3) . . . . ? C15 C14 C17 F143 -112.4(3) . . . . ? F13 C13 C12 C11 -177.3(3) . . . . ? C14 C13 C12 C11 0.9(4) . . . . ? C16 C11 C12 C13 -0.9(4) . . . . ? C10 C11 C12 C13 178.6(3) . . . . ? S12 N12 C10 N11 0.2(4) . . . . ? S12 N12 C10 C11 -177.9(2) . . . . ? S11 N11 C10 N12 -0.7(4) . . . . ? S11 N11 C10 C11 177.3(2) . . . . ? C12 C11 C10 N12 15.5(4) . . . . ? C16 C11 C10 N12 -165.1(3) . . . . ? C12 C11 C10 N11 -162.6(3) . . . . ? C16 C11 C10 N11 16.8(4) . . . . ? S21 N21 C20 N22 1.1(4) . . . . ? S21 N21 C20 C21 -178.1(2) . . . . ? S22 N22 C20 N21 -1.6(4) . . . . ? S22 N22 C20 C21 177.6(2) . . . . ? C11 C16 C15 C14 0.5(4) . . . . ? C13 C14 C15 C16 -0.5(4) . . . . ? C17 C14 C15 C16 177.8(3) . . . . ? C23 C22 C21 C26 -0.5(4) . . . . ? C23 C22 C21 C20 179.7(3) . . . . ? C25 C26 C21 C22 -0.7(4) . . . . ? C25 C26 C21 C20 179.1(3) . . . . ? N21 C20 C21 C22 -162.6(3) . . . . ? N22 C20 C21 C22 18.1(4) . . . . ? N21 C20 C21 C26 17.5(4) . . . . ? N22 C20 C21 C26 -161.8(3) . . . . ? #===END ######################################## ## Structure denoted 1(delta) in text ## ######################################## data_jr0250 _database_code_CSD 214202 _chemical_name_systematic ? _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C8 H3 F4 N2 S2, 0.26 SO2' ## SEE NOTE REGARDING SO2 IN _exptl_special_details _chemical_formula_sum 'C8 H3 F4 N2 S2' _chemical_formula_weight 267.24 ## Including 0.26 SO2, formula weight = 283.90 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' F F 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' S S 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting orthorhombic _symmetry_space_group_name_H-M Pbcn loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, -y+1/2, z+1/2' 'x+1/2, -y+1/2, -z' '-x, y, -z+1/2' '-x, -y, -z' 'x-1/2, y-1/2, -z-1/2' '-x-1/2, y-1/2, z' 'x, -y, z-1/2' _cell_length_a 17.1333(3) _cell_length_b 23.2358(4) _cell_length_c 10.6538(2) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 4241.34(13) _cell_formula_units_Z 16 _cell_measurement_temperature 180(2) _cell_measurement_reflns_used 15972 _cell_measurement_theta_min 1.02 _cell_measurement_theta_max 27.48 _exptl_crystal_description plate _exptl_crystal_colour red _exptl_crystal_size_max 0.21 _exptl_crystal_size_mid 0.16 _exptl_crystal_size_min 0.07 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.674 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 2128 _exptl_absorpt_coefficient_mu 0.529 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.917 _exptl_absorpt_correction_T_max 0.981 _exptl_absorpt_process_details 'Sortav Blessing (1995)' _exptl_special_details ; Crystals obtained by sublimation under ca. 0.33 atm. of SO2. Structure contains channels containing diffuse electron density. Chemical evidence suggests that this comprises SO2 molecules. The diffuse electron density could not be modelled, so was treated using the SQUEEZE procedure (van der Sluis and Spek, 1990), implemented in PLATON (Spek, 1998). The contribution of 266 electrons per unit cell was subtracted from F(obs). Before correction, R1 = 0.0905 and wR2 = 0.3401. On refinement against the corrected data, R1 = 0.0520, wR2 = 0.1513 (for the same SHELX job). This CIF contains the final structure refined against the "squeezed" data. ; _diffrn_ambient_temperature 180(2) _diffrn_radiation_wavelength 0.7107 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Nonius KappaCCD' _diffrn_measurement_method 'Thin slice \w and \f scans' _diffrn_standards_number 0 _diffrn_reflns_number 21236 _diffrn_reflns_av_R_equivalents 0.0614 _diffrn_reflns_av_sigmaI/netI 0.0531 _diffrn_reflns_limit_h_min -22 _diffrn_reflns_limit_h_max 22 _diffrn_reflns_limit_k_min -23 _diffrn_reflns_limit_k_max 30 _diffrn_reflns_limit_l_min -13 _diffrn_reflns_limit_l_max 13 _diffrn_reflns_theta_min 3.52 _diffrn_reflns_theta_max 27.48 _diffrn_measured_fraction_theta_max 0.996 _diffrn_reflns_theta_full 27.48 _diffrn_measured_fraction_theta_full 0.996 _reflns_number_total 4847 _reflns_number_gt 3449 _reflns_threshold_expression I>2\s(I) _computing_data_collection 'Collect (Nonius, 1998)' _computing_cell_refinement 'HKL Scalepack (Otwinowski & Minor, 1997)' _computing_data_reduction ; HKL Denzo and Scalepack (Otwinowski & Minor, 1997) ; _computing_structure_solution 'SIR-92 (Altomare et al., 1994)' _computing_structure_refinement 'SHELXTL v6.12 (Bruker AXS, 2001)' _computing_publication_material 'SHELXTL v6.12 (Bruker AXS, 2001)' _computing_molecular_graphics 'SHELXTL v6.12 (Bruker AXS, 2001)' _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^)+(0.0758P)^2^+1.4460P] 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 4847 _refine_ls_number_parameters 289 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0780 _refine_ls_R_factor_gt 0.0519 _refine_ls_wR_factor_ref 0.1460 _refine_ls_wR_factor_gt 0.1348 _refine_ls_goodness_of_fit_ref 1.071 _refine_ls_restrained_S_all 1.071 _refine_ls_shift/su_max 0.000 _refine_ls_shift/su_mean 0.000 _refine_diff_density_max 0.651 _refine_diff_density_min -0.466 _refine_diff_density_rms 0.106 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 S11 S 0.60881(5) -0.04570(3) 0.67785(7) 0.0387(2) Uani 1 1 d . . . S12 S 0.60252(4) -0.04589(3) 0.48138(7) 0.0365(2) Uani 1 1 d . . . S21 S 0.78850(5) -0.04838(3) 0.65829(7) 0.0386(2) Uani 1 1 d . . . S22 S 0.77884(5) -0.04577(3) 0.46312(7) 0.0393(2) Uani 1 1 d . . . F23 F 0.76080(11) 0.23785(7) 0.37760(16) 0.0479(5) Uani 1 1 d . . . F13 F 0.52519(10) 0.22774(7) 0.37220(16) 0.0475(4) Uani 1 1 d . . . F241 F 0.85487(11) 0.31649(7) 0.68866(17) 0.0509(5) Uani 1 1 d . . . F242 F 0.86871(11) 0.31724(7) 0.49027(18) 0.0526(5) Uani 1 1 d . . . F243 F 0.75466(11) 0.32341(7) 0.5715(2) 0.0624(6) Uani 1 1 d . . . F141 F 0.58806(12) 0.32422(7) 0.67759(18) 0.0557(5) Uani 1 1 d . . . F142 F 0.59665(11) 0.32343(7) 0.47794(18) 0.0526(5) Uani 1 1 d . . . F143 F 0.48495(10) 0.31146(8) 0.56662(19) 0.0580(5) Uani 1 1 d . . . N21 N 0.79507(14) 0.02141(10) 0.6741(2) 0.0366(5) Uani 1 1 d . . . N22 N 0.78341(15) 0.02458(10) 0.4545(2) 0.0368(5) Uani 1 1 d . . . N11 N 0.60464(14) 0.02478(9) 0.6899(2) 0.0366(5) Uani 1 1 d . . . N12 N 0.59643(14) 0.02443(9) 0.4696(2) 0.0337(5) Uani 1 1 d . . . C14 C 0.57340(15) 0.23450(11) 0.5778(3) 0.0325(6) Uani 1 1 d . . . C13 C 0.55470(15) 0.20105(11) 0.4737(2) 0.0323(6) Uani 1 1 d . . . C26 C 0.83139(16) 0.13998(11) 0.6757(2) 0.0328(6) Uani 1 1 d . . . H26 H 0.8468 0.1173 0.7457 0.039 Uiso 1 1 calc R . . C22 C 0.77678(15) 0.14638(11) 0.4675(2) 0.0323(6) Uani 1 1 d . . . H22 H 0.7564 0.1288 0.3939 0.039 Uiso 1 1 calc R . . C27 C 0.82298(16) 0.29668(12) 0.5822(3) 0.0355(6) Uani 1 1 d . . . C25 C 0.84037(15) 0.19921(11) 0.6795(2) 0.0324(6) Uani 1 1 d . . . H25 H 0.8636 0.2168 0.7508 0.039 Uiso 1 1 calc R . . C24 C 0.81547(14) 0.23323(11) 0.5792(2) 0.0282(5) Uani 1 1 d . . . C23 C 0.78447(15) 0.20534(12) 0.4757(3) 0.0322(6) Uani 1 1 d . . . C11 C 0.59076(15) 0.11499(10) 0.5792(2) 0.0286(5) Uani 1 1 d . . . C16 C 0.60960(16) 0.14726(11) 0.6846(2) 0.0342(6) Uani 1 1 d . . . H16 H 0.6282 0.1285 0.7581 0.041 Uiso 1 1 calc R . . C17 C 0.56083(17) 0.29809(12) 0.5741(3) 0.0398(7) Uani 1 1 d . . . C12 C 0.56325(15) 0.14251(11) 0.4720(2) 0.0323(6) Uani 1 1 d . . . H12 H 0.5506 0.1210 0.3989 0.039 Uiso 1 1 calc R . . C10 C 0.59823(16) 0.05157(11) 0.5802(2) 0.0315(6) Uani 1 1 d . . . C20 C 0.79190(16) 0.05023(11) 0.5656(2) 0.0324(6) Uani 1 1 d . . . C15 C 0.60143(16) 0.20659(12) 0.6834(3) 0.0376(6) Uani 1 1 d . . . H15 H 0.6152 0.2283 0.7556 0.045 Uiso 1 1 calc R . . C21 C 0.79975(14) 0.11344(11) 0.5697(2) 0.0279(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 S11 0.0622(5) 0.0268(4) 0.0271(4) 0.0018(3) 0.0082(3) -0.0055(3) S12 0.0538(4) 0.0272(4) 0.0284(4) -0.0029(3) -0.0006(3) -0.0062(3) S21 0.0632(5) 0.0235(3) 0.0290(4) 0.0021(3) -0.0029(3) -0.0028(3) S22 0.0656(5) 0.0250(4) 0.0273(4) -0.0030(3) 0.0066(3) -0.0052(3) F23 0.0702(12) 0.0357(9) 0.0378(10) 0.0128(7) -0.0182(8) -0.0069(8) F13 0.0642(11) 0.0435(9) 0.0347(10) 0.0042(8) -0.0113(8) -0.0013(8) F241 0.0777(12) 0.0300(8) 0.0449(11) -0.0068(8) -0.0083(9) -0.0104(8) F242 0.0704(12) 0.0384(9) 0.0490(11) 0.0088(8) 0.0113(9) -0.0163(8) F243 0.0484(10) 0.0325(9) 0.1064(18) -0.0024(9) -0.0068(10) 0.0091(8) F141 0.0804(13) 0.0351(9) 0.0516(12) -0.0138(8) -0.0041(10) -0.0004(8) F142 0.0705(12) 0.0360(9) 0.0514(11) 0.0074(8) 0.0125(9) -0.0029(8) F143 0.0476(10) 0.0475(10) 0.0790(15) -0.0047(10) 0.0027(9) 0.0123(8) N21 0.0599(15) 0.0230(11) 0.0269(12) 0.0011(9) -0.0042(11) -0.0052(10) N22 0.0588(15) 0.0287(12) 0.0227(12) -0.0018(9) 0.0037(10) -0.0049(11) N11 0.0595(15) 0.0250(11) 0.0253(12) -0.0011(9) 0.0068(10) -0.0042(10) N12 0.0500(13) 0.0273(11) 0.0238(12) -0.0022(9) -0.0014(10) -0.0050(10) C14 0.0342(13) 0.0292(13) 0.0342(15) -0.0016(11) 0.0071(11) -0.0040(11) C13 0.0329(13) 0.0380(14) 0.0260(13) 0.0051(11) -0.0011(11) -0.0034(11) C26 0.0469(15) 0.0283(13) 0.0233(13) 0.0022(10) 0.0001(11) -0.0012(11) C22 0.0399(14) 0.0341(14) 0.0229(13) -0.0008(11) 0.0006(11) -0.0052(11) C27 0.0372(14) 0.0301(14) 0.0391(16) 0.0016(12) 0.0013(12) -0.0039(11) C25 0.0422(15) 0.0280(13) 0.0271(14) -0.0032(11) 0.0008(11) -0.0033(11) C24 0.0309(12) 0.0239(12) 0.0298(14) -0.0012(10) 0.0058(10) -0.0031(10) C23 0.0355(13) 0.0348(14) 0.0262(13) 0.0081(11) 0.0000(11) -0.0037(11) C11 0.0346(13) 0.0269(13) 0.0244(13) 0.0007(10) 0.0036(10) -0.0032(10) C16 0.0492(16) 0.0318(14) 0.0216(13) 0.0001(11) 0.0000(11) -0.0002(12) C17 0.0453(16) 0.0359(15) 0.0383(16) -0.0035(13) 0.0086(13) 0.0022(12) C12 0.0386(14) 0.0316(13) 0.0267(14) -0.0025(11) -0.0004(11) -0.0076(11) C10 0.0422(14) 0.0287(13) 0.0238(13) 0.0007(11) 0.0011(11) -0.0050(11) C20 0.0465(15) 0.0286(14) 0.0221(13) -0.0005(10) 0.0010(11) -0.0051(11) C15 0.0492(16) 0.0364(15) 0.0273(14) -0.0070(12) 0.0013(12) -0.0047(12) C21 0.0372(13) 0.0228(12) 0.0238(13) 0.0000(10) 0.0020(10) -0.0030(10) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag S11 N11 1.644(2) . ? S11 S12 2.0959(10) . ? S12 N12 1.642(2) . ? S21 N21 1.634(2) . ? S21 S22 2.0867(10) . ? S22 N22 1.639(2) . ? F23 C23 1.352(3) . ? F13 C13 1.345(3) . ? F241 C27 1.341(3) . ? F242 C27 1.342(3) . ? F243 C27 1.330(3) . ? F141 C17 1.342(3) . ? F142 C17 1.331(3) . ? F143 C17 1.339(3) . ? N21 C20 1.337(3) . ? N22 C20 1.333(3) . ? N11 C10 1.329(3) . ? N12 C10 1.337(3) . ? C14 C15 1.384(4) . ? C14 C13 1.392(4) . ? C14 C17 1.494(4) . ? C13 C12 1.368(4) . ? C26 C25 1.385(4) . ? C26 C21 1.396(4) . ? C26 H26 0.9500 . ? C22 C23 1.379(4) . ? C22 C21 1.389(4) . ? C22 H22 0.9500 . ? C27 C24 1.480(4) . ? C25 C24 1.396(4) . ? C25 H25 0.9500 . ? C24 C23 1.384(4) . ? C11 C16 1.389(4) . ? C11 C12 1.391(4) . ? C11 C10 1.479(3) . ? C16 C15 1.386(4) . ? C16 H16 0.9500 . ? C12 H12 0.9500 . ? C20 C21 1.475(3) . ? C15 H15 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 N11 S11 S12 94.45(9) . . ? N12 S12 S11 94.46(8) . . ? N21 S21 S22 94.55(9) . . ? N22 S22 S21 94.64(9) . . ? C20 N21 S21 113.90(19) . . ? C20 N22 S22 113.68(19) . . ? C10 N11 S11 113.68(19) . . ? C10 N12 S12 113.60(19) . . ? C15 C14 C13 117.8(2) . . ? C15 C14 C17 122.3(2) . . ? C13 C14 C17 119.9(2) . . ? F13 C13 C12 119.2(2) . . ? F13 C13 C14 118.0(2) . . ? C12 C13 C14 122.7(2) . . ? C25 C26 C21 120.3(2) . . ? C25 C26 H26 119.8 . . ? C21 C26 H26 119.8 . . ? C23 C22 C21 118.1(2) . . ? C23 C22 H22 121.0 . . ? C21 C22 H22 121.0 . . ? F243 C27 F241 105.7(2) . . ? F243 C27 F242 106.6(2) . . ? F241 C27 F242 104.9(2) . . ? F243 C27 C24 112.8(2) . . ? F241 C27 C24 113.3(2) . . ? F242 C27 C24 112.9(2) . . ? C26 C25 C24 120.4(2) . . ? C26 C25 H25 119.8 . . ? C24 C25 H25 119.8 . . ? C23 C24 C25 117.5(2) . . ? C23 C24 C27 121.1(2) . . ? C25 C24 C27 121.4(2) . . ? F23 C23 C22 118.5(2) . . ? F23 C23 C24 118.0(2) . . ? C22 C23 C24 123.6(2) . . ? C16 C11 C12 119.7(2) . . ? C16 C11 C10 120.8(2) . . ? C12 C11 C10 119.6(2) . . ? C15 C16 C11 120.4(2) . . ? C15 C16 H16 119.8 . . ? C11 C16 H16 119.8 . . ? F142 C17 F143 107.4(2) . . ? F142 C17 F141 105.8(2) . . ? F143 C17 F141 106.3(2) . . ? F142 C17 C14 113.0(2) . . ? F143 C17 C14 111.8(2) . . ? F141 C17 C14 112.1(2) . . ? C13 C12 C11 118.8(2) . . ? C13 C12 H12 120.6 . . ? C11 C12 H12 120.6 . . ? N11 C10 N12 123.8(2) . . ? N11 C10 C11 118.7(2) . . ? N12 C10 C11 117.5(2) . . ? N22 C20 N21 123.2(2) . . ? N22 C20 C21 118.8(2) . . ? N21 C20 C21 118.0(2) . . ? C14 C15 C16 120.6(2) . . ? C14 C15 H15 119.7 . . ? C16 C15 H15 119.7 . . ? C22 C21 C26 120.1(2) . . ? C22 C21 C20 120.0(2) . . ? C26 C21 C20 119.9(2) . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag N11 S11 S12 N12 -0.70(12) . . . . ? N21 S21 S22 N22 -0.49(13) . . . . ? S22 S21 N21 C20 0.1(2) . . . . ? S21 S22 N22 C20 0.9(2) . . . . ? S12 S11 N11 C10 0.9(2) . . . . ? S11 S12 N12 C10 0.4(2) . . . . ? C15 C14 C13 F13 178.0(2) . . . . ? C17 C14 C13 F13 -0.3(4) . . . . ? C15 C14 C13 C12 -0.3(4) . . . . ? C17 C14 C13 C12 -178.6(2) . . . . ? C21 C26 C25 C24 2.2(4) . . . . ? C26 C25 C24 C23 -2.2(4) . . . . ? C26 C25 C24 C27 178.7(2) . . . . ? F243 C27 C24 C23 60.6(3) . . . . ? F241 C27 C24 C23 -179.3(2) . . . . ? F242 C27 C24 C23 -60.2(3) . . . . ? F243 C27 C24 C25 -120.3(3) . . . . ? F241 C27 C24 C25 -0.3(4) . . . . ? F242 C27 C24 C25 118.8(3) . . . . ? C21 C22 C23 F23 -178.7(2) . . . . ? C21 C22 C23 C24 1.6(4) . . . . ? C25 C24 C23 F23 -179.4(2) . . . . ? C27 C24 C23 F23 -0.4(4) . . . . ? C25 C24 C23 C22 0.3(4) . . . . ? C27 C24 C23 C22 179.4(2) . . . . ? C12 C11 C16 C15 -0.3(4) . . . . ? C10 C11 C16 C15 -179.1(2) . . . . ? C15 C14 C17 F142 126.5(3) . . . . ? C13 C14 C17 F142 -55.2(3) . . . . ? C15 C14 C17 F143 -112.1(3) . . . . ? C13 C14 C17 F143 66.1(3) . . . . ? C15 C14 C17 F141 7.1(4) . . . . ? C13 C14 C17 F141 -174.6(2) . . . . ? F13 C13 C12 C11 -177.4(2) . . . . ? C14 C13 C12 C11 0.9(4) . . . . ? C16 C11 C12 C13 -0.6(4) . . . . ? C10 C11 C12 C13 178.3(2) . . . . ? S11 N11 C10 N12 -0.9(4) . . . . ? S11 N11 C10 C11 177.57(19) . . . . ? S12 N12 C10 N11 0.3(4) . . . . ? S12 N12 C10 C11 -178.26(19) . . . . ? C16 C11 C10 N11 16.2(4) . . . . ? C12 C11 C10 N11 -162.7(2) . . . . ? C16 C11 C10 N12 -165.2(2) . . . . ? C12 C11 C10 N12 15.9(4) . . . . ? S22 N22 C20 N21 -1.1(4) . . . . ? S22 N22 C20 C21 177.7(2) . . . . ? S21 N21 C20 N22 0.6(4) . . . . ? S21 N21 C20 C21 -178.18(19) . . . . ? C13 C14 C15 C16 -0.6(4) . . . . ? C17 C14 C15 C16 177.6(2) . . . . ? C11 C16 C15 C14 0.9(4) . . . . ? C23 C22 C21 C26 -1.6(4) . . . . ? C23 C22 C21 C20 179.4(2) . . . . ? C25 C26 C21 C22 -0.3(4) . . . . ? C25 C26 C21 C20 178.8(2) . . . . ? N22 C20 C21 C22 18.1(4) . . . . ? N21 C20 C21 C22 -163.0(3) . . . . ? N22 C20 C21 C26 -160.9(3) . . . . ? N21 C20 C21 C26 18.0(4) . . . . ? #===END